# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 loop_ _publ_author_name 'Jonathan White' 'Marissa Spiniello' _publ_contact_author_name 'Dr Jonathan White' _publ_contact_author_address ; Chemistry University of Melbourne Parkville Melbourne VIC 3010 AUSTRALIA ; _publ_contact_author_email WHITEJM@UNIMELB.EDU.AU _publ_section_title ; Low temperature X-ray structural studies of the ester and ether derivatives of cis- and trans-4-tert-butyl cyclohexanol and 2-adamantanol; An attempt to determine the relative s-donor ability of C-H and C-C bonds ; data_compound4e _database_code_CSD 205439 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 89.5-90.5 _chemical_formula_moiety ? _chemical_formula_sum 'C17 H22 N2 O6' _chemical_formula_weight 350.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.388(5) _cell_length_b 7.1290(10) _cell_length_c 16.839(6) _cell_angle_alpha 90.00 _cell_angle_beta 112.56(3) _cell_angle_gamma 90.00 _cell_volume 1705.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 130.0(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 15 _exptl_crystal_description slabs _exptl_crystal_colour yellow _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130.0(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method \q2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 9600 _diffrn_standards_decay_% 2 _diffrn_reflns_number 3114 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2993 _reflns_number_gt 2323 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software 5.0 (Enraf-Nonius, 1989)' _computing_cell_refinement ? _computing_data_reduction 'PROCESS_DATA (Gable et al., 1994)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0619P)^2^+0.3901P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0053(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2993 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0610 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1147 _refine_ls_wR_factor_gt 0.1032 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.72333(14) 0.5798(3) 0.05189(13) 0.0252(4) Uani 1 1 d . . . H1 H 0.7334 0.4554 0.0293 0.030 Uiso 1 1 calc R . . C2 C 0.61885(14) 0.6181(3) 0.02241(13) 0.0272(4) Uani 1 1 d . . . H2A H 0.5880 0.5081 0.0363 0.033 Uiso 1 1 calc R . . H2B H 0.5921 0.6339 -0.0408 0.033 Uiso 1 1 calc R . . C3 C 0.59658(13) 0.7923(3) 0.06375(12) 0.0238(4) Uani 1 1 d . . . H3A H 0.5275 0.8040 0.0455 0.029 Uiso 1 1 calc R . . H3B H 0.6196 0.9049 0.0434 0.029 Uiso 1 1 calc R . . C4 C 0.64212(13) 0.7838(3) 0.16209(12) 0.0213(4) Uani 1 1 d . . . H4 H 0.6178 0.6677 0.1798 0.026 Uiso 1 1 calc R . . C5 C 0.74868(13) 0.7566(3) 0.18905(12) 0.0236(4) Uani 1 1 d . . . H5A H 0.7753 0.8681 0.1715 0.028 Uiso 1 1 calc R . . H5B H 0.7785 0.7466 0.2525 0.028 Uiso 1 1 calc R . . C6 C 0.77208(14) 0.5819(3) 0.14896(12) 0.0258(4) Uani 1 1 d . . . H6A H 0.8410 0.5757 0.1649 0.031 Uiso 1 1 calc R . . H6B H 0.7531 0.4693 0.1727 0.031 Uiso 1 1 calc R . . C7 C 0.61510(13) 0.9508(3) 0.20753(12) 0.0238(4) Uani 1 1 d . . . C8 C 0.64759(15) 1.1391(3) 0.18508(14) 0.0297(5) Uani 1 1 d . . . H8A H 0.7159 1.1364 0.2009 0.045 Uiso 1 1 calc R . . H8B H 0.6316 1.2397 0.2167 0.045 Uiso 1 1 calc R . . H8C H 0.6162 1.1618 0.1232 0.045 Uiso 1 1 calc R . . C9 C 0.66088(15) 0.9241(3) 0.30551(13) 0.0308(5) Uani 1 1 d . . . H9A H 0.7294 0.9193 0.3236 0.046 Uiso 1 1 calc R . . H9B H 0.6386 0.8067 0.3213 0.046 Uiso 1 1 calc R . . H9C H 0.6438 1.0294 0.3341 0.046 Uiso 1 1 calc R . . C10 C 0.50833(14) 0.9561(3) 0.18173(14) 0.0314(5) Uani 1 1 d . . . H10A H 0.4917 1.0624 0.2101 0.047 Uiso 1 1 calc R . . H10B H 0.4875 0.8391 0.1994 0.047 Uiso 1 1 calc R . . H10C H 0.4774 0.9703 0.1192 0.047 Uiso 1 1 calc R . . C11 C 0.84148(13) 0.6946(3) 0.00463(12) 0.0227(4) Uani 1 1 d . . . C12 C 0.86919(13) 0.8504(3) -0.04093(11) 0.0209(4) Uani 1 1 d . . . C13 C 0.83455(12) 1.0331(3) -0.04923(11) 0.0204(4) Uani 1 1 d . . . C14 C 0.85605(13) 1.1673(3) -0.09753(12) 0.0231(4) Uani 1 1 d . . . H14 H 0.8308 1.2905 -0.1033 0.028 Uiso 1 1 calc R . . C15 C 0.91591(13) 1.1152(3) -0.13733(12) 0.0224(4) Uani 1 1 d . . . C16 C 0.95376(13) 0.9374(3) -0.13050(12) 0.0234(4) Uani 1 1 d . . . H16 H 0.9952 0.9063 -0.1583 0.028 Uiso 1 1 calc R . . C17 C 0.92966(13) 0.8056(3) -0.08198(12) 0.0224(4) Uani 1 1 d . . . H17 H 0.9548 0.6824 -0.0766 0.027 Uiso 1 1 calc R . . N1 N 0.77733(11) 1.0995(2) -0.00208(11) 0.0235(4) Uani 1 1 d . . . N2 N 0.94115(12) 1.2581(2) -0.18833(11) 0.0289(4) Uani 1 1 d . . . O1 O 0.76166(9) 0.73029(18) 0.01427(8) 0.0216(3) Uani 1 1 d . . . O2 O 0.88637(10) 0.5506(2) 0.02498(10) 0.0331(4) Uani 1 1 d . . . O3 O 0.81521(10) 1.1043(2) 0.07652(9) 0.0294(3) Uani 1 1 d . . . O4 O 0.69733(10) 1.1520(2) -0.04435(10) 0.0342(4) Uani 1 1 d . . . O5 O 0.90349(11) 1.4123(2) -0.19672(10) 0.0391(4) Uani 1 1 d . . . O6 O 0.99891(13) 1.2138(2) -0.21819(12) 0.0470(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0341(11) 0.0144(9) 0.0312(10) -0.0012(8) 0.0170(9) -0.0028(8) C2 0.0310(10) 0.0245(10) 0.0270(10) -0.0041(8) 0.0121(9) -0.0073(9) C3 0.0212(9) 0.0253(10) 0.0226(10) -0.0002(8) 0.0057(8) -0.0006(8) C4 0.0247(10) 0.0171(9) 0.0223(10) 0.0020(7) 0.0091(8) -0.0021(7) C5 0.0254(10) 0.0244(10) 0.0194(9) 0.0020(8) 0.0067(8) -0.0006(8) C6 0.0280(10) 0.0182(9) 0.0320(11) 0.0076(8) 0.0122(8) 0.0029(8) C7 0.0279(10) 0.0214(10) 0.0226(9) 0.0009(8) 0.0102(8) -0.0013(8) C8 0.0398(12) 0.0186(10) 0.0342(11) -0.0004(8) 0.0181(9) 0.0004(9) C9 0.0385(11) 0.0296(11) 0.0253(10) -0.0024(9) 0.0132(9) -0.0017(9) C10 0.0308(11) 0.0307(11) 0.0347(11) -0.0001(9) 0.0150(9) 0.0031(9) C11 0.0273(10) 0.0185(10) 0.0223(9) -0.0037(7) 0.0095(8) 0.0020(8) C12 0.0211(9) 0.0190(9) 0.0189(9) -0.0027(7) 0.0037(7) 0.0004(8) C13 0.0195(9) 0.0196(9) 0.0205(9) -0.0039(7) 0.0059(7) 0.0011(8) C14 0.0218(9) 0.0197(9) 0.0248(10) -0.0003(8) 0.0056(8) 0.0012(8) C15 0.0213(9) 0.0229(10) 0.0208(9) -0.0002(8) 0.0057(7) -0.0038(8) C16 0.0210(9) 0.0268(10) 0.0219(9) -0.0071(8) 0.0077(7) -0.0020(8) C17 0.0237(9) 0.0186(9) 0.0222(9) -0.0037(7) 0.0057(8) 0.0020(8) N1 0.0268(9) 0.0139(8) 0.0329(10) -0.0015(7) 0.0148(7) -0.0002(7) N2 0.0301(9) 0.0283(10) 0.0295(9) -0.0002(7) 0.0127(8) -0.0047(8) O1 0.0269(7) 0.0145(6) 0.0251(7) -0.0002(5) 0.0120(6) -0.0002(5) O2 0.0411(9) 0.0231(8) 0.0418(9) 0.0073(6) 0.0234(7) 0.0113(7) O3 0.0396(8) 0.0247(7) 0.0281(8) -0.0036(6) 0.0178(6) -0.0011(6) O4 0.0255(8) 0.0315(8) 0.0465(9) -0.0007(7) 0.0147(7) 0.0061(6) O5 0.0414(9) 0.0293(9) 0.0504(10) 0.0137(7) 0.0216(8) 0.0053(7) O6 0.0611(11) 0.0364(9) 0.0650(11) 0.0050(8) 0.0482(10) 0.0009(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.479(2) . ? C1 C6 1.515(3) . ? C1 C2 1.514(3) . ? C1 H1 1.0000 . ? C2 C3 1.525(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.532(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.537(3) . ? C4 C7 1.555(3) . ? C4 H4 1.0000 . ? C5 C6 1.524(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.530(3) . ? C7 C10 1.530(3) . ? C7 C9 1.537(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 O2 1.211(2) . ? C11 O1 1.324(2) . ? C11 C12 1.502(3) . ? C12 C17 1.392(3) . ? C12 C13 1.394(3) . ? C13 C14 1.376(3) . ? C13 N1 1.472(2) . ? C14 C15 1.382(3) . ? C14 H14 0.9500 . ? C15 C16 1.381(3) . ? C15 N2 1.477(3) . ? C16 C17 1.386(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? N1 O4 1.221(2) . ? N1 O3 1.225(2) . ? N2 O6 1.219(2) . ? N2 O5 1.225(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C6 109.95(15) . . ? O1 C1 C2 106.05(15) . . ? C6 C1 C2 112.08(16) . . ? O1 C1 H1 109.6 . . ? C6 C1 H1 109.6 . . ? C2 C1 H1 109.6 . . ? C1 C2 C3 113.16(16) . . ? C1 C2 H2A 108.9 . . ? C3 C2 H2A 108.9 . . ? C1 C2 H2B 108.9 . . ? C3 C2 H2B 108.9 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C4 111.82(16) . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 107.9 . . ? C3 C4 C5 108.54(15) . . ? C3 C4 C7 113.83(15) . . ? C5 C4 C7 114.05(15) . . ? C3 C4 H4 106.6 . . ? C5 C4 H4 106.6 . . ? C7 C4 H4 106.6 . . ? C6 C5 C4 112.26(16) . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5B 109.2 . . ? C4 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C1 C6 C5 112.51(16) . . ? C1 C6 H6A 109.1 . . ? C5 C6 H6A 109.1 . . ? C1 C6 H6B 109.1 . . ? C5 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? C8 C7 C10 108.98(17) . . ? C8 C7 C9 108.36(16) . . ? C10 C7 C9 107.93(16) . . ? C8 C7 C4 112.06(15) . . ? C10 C7 C4 109.87(16) . . ? C9 C7 C4 109.54(16) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O2 C11 O1 125.71(18) . . ? O2 C11 C12 121.91(17) . . ? O1 C11 C12 112.26(16) . . ? C17 C12 C13 117.87(18) . . ? C17 C12 C11 117.29(17) . . ? C13 C12 C11 124.73(17) . . ? C14 C13 C12 122.66(18) . . ? C14 C13 N1 115.12(16) . . ? C12 C13 N1 122.10(17) . . ? C13 C14 C15 117.13(18) . . ? C13 C14 H14 121.4 . . ? C15 C14 H14 121.4 . . ? C14 C15 C16 122.99(18) . . ? C14 C15 N2 118.01(17) . . ? C16 C15 N2 118.99(17) . . ? C15 C16 C17 118.15(18) . . ? C15 C16 H16 120.9 . . ? C17 C16 H16 120.9 . . ? C16 C17 C12 121.19(18) . . ? C16 C17 H17 119.4 . . ? C12 C17 H17 119.4 . . ? O4 N1 O3 125.22(17) . . ? O4 N1 C13 117.53(16) . . ? O3 N1 C13 117.19(15) . . ? O6 N2 O5 124.93(18) . . ? O6 N2 C15 117.21(17) . . ? O5 N2 C15 117.86(16) . . ? C11 O1 C1 117.01(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -69.63(19) . . . . ? C6 C1 C2 C3 50.4(2) . . . . ? C1 C2 C3 C4 -54.5(2) . . . . ? C2 C3 C4 C5 56.4(2) . . . . ? C2 C3 C4 C7 -175.43(16) . . . . ? C3 C4 C5 C6 -56.9(2) . . . . ? C7 C4 C5 C6 175.07(15) . . . . ? O1 C1 C6 C5 67.5(2) . . . . ? C2 C1 C6 C5 -50.2(2) . . . . ? C4 C5 C6 C1 54.8(2) . . . . ? C3 C4 C7 C8 -62.2(2) . . . . ? C5 C4 C7 C8 63.1(2) . . . . ? C3 C4 C7 C10 59.1(2) . . . . ? C5 C4 C7 C10 -175.55(16) . . . . ? C3 C4 C7 C9 177.55(15) . . . . ? C5 C4 C7 C9 -57.2(2) . . . . ? O2 C11 C12 C17 18.9(3) . . . . ? O1 C11 C12 C17 -157.40(16) . . . . ? O2 C11 C12 C13 -165.01(18) . . . . ? O1 C11 C12 C13 18.7(3) . . . . ? C17 C12 C13 C14 1.5(3) . . . . ? C11 C12 C13 C14 -174.53(17) . . . . ? C17 C12 C13 N1 -174.28(16) . . . . ? C11 C12 C13 N1 9.7(3) . . . . ? C12 C13 C14 C15 -1.2(3) . . . . ? N1 C13 C14 C15 174.92(16) . . . . ? C13 C14 C15 C16 0.1(3) . . . . ? C13 C14 C15 N2 -179.01(16) . . . . ? C14 C15 C16 C17 0.5(3) . . . . ? N2 C15 C16 C17 179.64(16) . . . . ? C15 C16 C17 C12 -0.2(3) . . . . ? C13 C12 C17 C16 -0.8(3) . . . . ? C11 C12 C17 C16 175.52(17) . . . . ? C14 C13 N1 O4 65.2(2) . . . . ? C12 C13 N1 O4 -118.70(19) . . . . ? C14 C13 N1 O3 -112.05(19) . . . . ? C12 C13 N1 O3 64.1(2) . . . . ? C14 C15 N2 O6 175.16(18) . . . . ? C16 C15 N2 O6 -4.0(3) . . . . ? C14 C15 N2 O5 -4.1(3) . . . . ? C16 C15 N2 O5 176.79(17) . . . . ? O2 C11 O1 C1 -1.1(3) . . . . ? C12 C11 O1 C1 175.08(14) . . . . ? C6 C1 O1 C11 81.80(19) . . . . ? C2 C1 O1 C11 -156.83(15) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.283 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.047 data_compound4f _database_code_CSD 205440 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 118-119.5 _chemical_formula_moiety ? _chemical_formula_sum 'C17 H22 N2 O6' _chemical_formula_weight 350.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.441(2) _cell_length_b 5.981(2) _cell_length_c 18.722(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.47(2) _cell_angle_gamma 90.00 _cell_volume 1735.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 130.0(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 20 _cell_measurement_theta_max 25 _exptl_crystal_description needles _exptl_crystal_colour yellow _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.856 _exptl_absorpt_correction_type Analytical _exptl_absorpt_correction_T_min 0.69 _exptl_absorpt_correction_T_max 0.95 _exptl_absorpt_process_details 'ABSORB Platon' _exptl_special_details ; ? ; _diffrn_ambient_temperature 130.0(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method \q2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 9600 _diffrn_standards_decay_% 2 _diffrn_reflns_number 3027 _diffrn_reflns_av_R_equivalents 0.0080 _diffrn_reflns_av_sigmaI/netI 0.0172 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.87 _diffrn_reflns_theta_max 65.00 _reflns_number_total 2923 _reflns_number_gt 2622 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software 5.0 (Enraf-Nonius, 1989)' _computing_cell_refinement ? _computing_data_reduction 'PROCESS_DATA (Gable et al., 1994)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0621P)^2^+0.6469P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0049(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2923 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.1048 _refine_ls_wR_factor_gt 0.1014 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.75206(9) 0.2376(2) 0.11422(8) 0.0277(3) Uani 1 1 d . . . H1 H 0.7409 0.2934 0.0615 0.033 Uiso 1 1 calc R . . C2 C 0.82532(9) 0.0697(3) 0.13480(8) 0.0300(3) Uani 1 1 d . . . H2A H 0.8751 0.1355 0.1237 0.036 Uiso 1 1 calc R . . H2B H 0.8067 -0.0648 0.1027 0.036 Uiso 1 1 calc R . . C3 C 0.85412(9) 0.0001(2) 0.21788(8) 0.0286(3) Uani 1 1 d . . . H3A H 0.9048 -0.0999 0.2288 0.034 Uiso 1 1 calc R . . H3B H 0.8071 -0.0848 0.2275 0.034 Uiso 1 1 calc R . . C4 C 0.87776(8) 0.2023(2) 0.27135(8) 0.0254(3) Uani 1 1 d . . . H4 H 0.9241 0.2854 0.2589 0.030 Uiso 1 1 calc R . . C5 C 0.79926(9) 0.3580(2) 0.25149(8) 0.0289(3) Uani 1 1 d . . . H5A H 0.7509 0.2794 0.2610 0.035 Uiso 1 1 calc R . . H5B H 0.8137 0.4912 0.2848 0.035 Uiso 1 1 calc R . . C6 C 0.77105(9) 0.4326(2) 0.16897(9) 0.0302(3) Uani 1 1 d . . . H6A H 0.7187 0.5265 0.1580 0.036 Uiso 1 1 calc R . . H6B H 0.8171 0.5256 0.1611 0.036 Uiso 1 1 calc R . . C7 C 0.91561(9) 0.1386(2) 0.35656(8) 0.0275(3) Uani 1 1 d . . . C8 C 0.84922(10) 0.0217(3) 0.38448(9) 0.0374(4) Uani 1 1 d . . . H8A H 0.7992 0.1198 0.3766 0.056 Uiso 1 1 calc R . . H8B H 0.8752 -0.0120 0.4386 0.056 Uiso 1 1 calc R . . H8C H 0.8307 -0.1177 0.3562 0.056 Uiso 1 1 calc R . . C9 C 0.99316(10) -0.0162(3) 0.36928(9) 0.0361(4) Uani 1 1 d . . . H9A H 1.0361 0.0574 0.3515 0.054 Uiso 1 1 calc R . . H9B H 0.9743 -0.1556 0.3411 0.054 Uiso 1 1 calc R . . H9C H 1.0188 -0.0496 0.4234 0.054 Uiso 1 1 calc R . . C10 C 0.94815(10) 0.3490(3) 0.40428(9) 0.0354(4) Uani 1 1 d . . . H10A H 0.9908 0.4248 0.3866 0.053 Uiso 1 1 calc R . . H10B H 0.9749 0.3069 0.4576 0.053 Uiso 1 1 calc R . . H10C H 0.8995 0.4499 0.3991 0.053 Uiso 1 1 calc R . . C11 C 0.59970(9) 0.2060(2) 0.08213(7) 0.0239(3) Uani 1 1 d . . . C12 C 0.52764(8) 0.0755(2) 0.09365(7) 0.0223(3) Uani 1 1 d . . . C13 C 0.54188(9) -0.1248(2) 0.13369(7) 0.0251(3) Uani 1 1 d . . . H13 H 0.5983 -0.1856 0.1541 0.030 Uiso 1 1 calc R . . C14 C 0.47199(9) -0.2327(2) 0.14290(7) 0.0256(3) Uani 1 1 d . . . C15 C 0.38924(10) -0.1510(2) 0.11525(7) 0.0278(3) Uani 1 1 d . . . H15 H 0.3422 -0.2277 0.1228 0.033 Uiso 1 1 calc R . . C16 C 0.37792(9) 0.0490(2) 0.07584(7) 0.0248(3) Uani 1 1 d . . . C17 C 0.44503(9) 0.1639(2) 0.06378(7) 0.0232(3) Uani 1 1 d . . . H17 H 0.4350 0.2996 0.0358 0.028 Uiso 1 1 calc R . . N1 N 0.48692(9) -0.4433(2) 0.18613(6) 0.0317(3) Uani 1 1 d . . . N2 N 0.29108(8) 0.1462(2) 0.04729(7) 0.0307(3) Uani 1 1 d . . . O1 O 0.67630(6) 0.11460(16) 0.11842(5) 0.0265(3) Uani 1 1 d . . . O2 O 0.58821(6) 0.37349(17) 0.04430(6) 0.0313(3) Uani 1 1 d . . . O3 O 0.56050(8) -0.51668(18) 0.21050(6) 0.0388(3) Uani 1 1 d . . . O4 O 0.42428(8) -0.53658(19) 0.19452(6) 0.0418(3) Uani 1 1 d . . . O5 O 0.23166(7) 0.0366(2) 0.05454(7) 0.0468(3) Uani 1 1 d . . . O6 O 0.28245(7) 0.32917(19) 0.01698(7) 0.0415(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0244(7) 0.0255(8) 0.0324(7) 0.0032(6) 0.0083(6) -0.0026(6) C2 0.0281(7) 0.0270(8) 0.0342(8) -0.0040(6) 0.0094(6) 0.0013(6) C3 0.0271(7) 0.0212(7) 0.0352(8) -0.0019(6) 0.0074(6) 0.0046(6) C4 0.0236(7) 0.0202(7) 0.0328(7) -0.0010(6) 0.0099(6) -0.0004(5) C5 0.0288(7) 0.0196(7) 0.0372(8) -0.0037(6) 0.0094(6) 0.0022(6) C6 0.0257(7) 0.0201(7) 0.0418(8) 0.0013(6) 0.0070(6) 0.0008(6) C7 0.0280(7) 0.0230(7) 0.0315(7) -0.0003(6) 0.0100(6) 0.0001(6) C8 0.0410(8) 0.0351(9) 0.0393(8) 0.0024(7) 0.0178(7) -0.0031(7) C9 0.0344(8) 0.0359(9) 0.0350(8) 0.0028(7) 0.0078(6) 0.0086(7) C10 0.0374(8) 0.0320(8) 0.0347(8) -0.0040(7) 0.0090(6) -0.0023(7) C11 0.0270(7) 0.0217(7) 0.0213(6) 0.0006(6) 0.0058(5) 0.0015(5) C12 0.0279(7) 0.0206(7) 0.0173(6) -0.0019(5) 0.0062(5) -0.0011(5) C13 0.0334(7) 0.0217(7) 0.0188(6) -0.0023(5) 0.0070(5) -0.0003(6) C14 0.0421(8) 0.0181(7) 0.0173(6) -0.0011(5) 0.0106(6) -0.0027(6) C15 0.0391(8) 0.0251(7) 0.0228(7) -0.0041(6) 0.0148(6) -0.0088(6) C16 0.0290(7) 0.0251(7) 0.0209(6) -0.0027(5) 0.0090(5) -0.0021(6) C17 0.0311(7) 0.0198(7) 0.0194(6) -0.0014(5) 0.0095(5) -0.0014(5) N1 0.0543(8) 0.0210(6) 0.0201(6) -0.0013(5) 0.0126(6) -0.0050(6) N2 0.0302(6) 0.0328(7) 0.0327(6) -0.0003(5) 0.0151(5) -0.0033(5) O1 0.0237(5) 0.0217(5) 0.0311(5) 0.0036(4) 0.0050(4) -0.0006(4) O2 0.0281(5) 0.0294(6) 0.0351(6) 0.0122(5) 0.0090(4) 0.0012(4) O3 0.0592(7) 0.0264(6) 0.0299(6) 0.0064(4) 0.0136(5) 0.0075(5) O4 0.0642(8) 0.0304(6) 0.0330(6) 0.0029(5) 0.0190(5) -0.0158(5) O5 0.0348(6) 0.0467(7) 0.0660(8) 0.0086(6) 0.0263(6) -0.0056(5) O6 0.0335(6) 0.0375(7) 0.0552(7) 0.0151(5) 0.0169(5) 0.0049(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.4712(16) . ? C1 C2 1.516(2) . ? C1 C6 1.515(2) . ? C1 H1 1.0000 . ? C2 C3 1.525(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5350(19) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5334(19) . ? C4 C7 1.554(2) . ? C4 H4 1.0000 . ? C5 C6 1.524(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.528(2) . ? C7 C9 1.529(2) . ? C7 C10 1.533(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 O2 1.2049(17) . ? C11 O1 1.3326(16) . ? C11 C12 1.4931(19) . ? C12 C17 1.389(2) . ? C12 C13 1.391(2) . ? C13 C14 1.378(2) . ? C13 H13 0.9500 . ? C14 C15 1.374(2) . ? C14 N1 1.4730(18) . ? C15 C16 1.385(2) . ? C15 H15 0.9500 . ? C16 C17 1.3807(19) . ? C16 N2 1.4676(19) . ? C17 H17 0.9500 . ? N1 O3 1.2231(17) . ? N1 O4 1.2265(17) . ? N2 O6 1.2188(17) . ? N2 O5 1.2212(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 105.68(11) . . ? O1 C1 C6 109.64(11) . . ? C2 C1 C6 111.77(12) . . ? O1 C1 H1 109.9 . . ? C2 C1 H1 109.9 . . ? C6 C1 H1 109.9 . . ? C1 C2 C3 112.99(12) . . ? C1 C2 H2A 109.0 . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2B 109.0 . . ? C3 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C4 112.01(12) . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C5 C4 C3 108.10(11) . . ? C5 C4 C7 114.48(11) . . ? C3 C4 C7 113.82(11) . . ? C5 C4 H4 106.6 . . ? C3 C4 H4 106.6 . . ? C7 C4 H4 106.6 . . ? C6 C5 C4 111.76(12) . . ? C6 C5 H5A 109.3 . . ? C4 C5 H5A 109.3 . . ? C6 C5 H5B 109.3 . . ? C4 C5 H5B 109.3 . . ? H5A C5 H5B 107.9 . . ? C1 C6 C5 112.62(12) . . ? C1 C6 H6A 109.1 . . ? C5 C6 H6A 109.1 . . ? C1 C6 H6B 109.1 . . ? C5 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? C8 C7 C9 108.88(12) . . ? C8 C7 C10 109.06(12) . . ? C9 C7 C10 107.18(12) . . ? C8 C7 C4 112.10(12) . . ? C9 C7 C4 109.64(11) . . ? C10 C7 C4 109.84(12) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O2 C11 O1 125.25(13) . . ? O2 C11 C12 122.88(12) . . ? O1 C11 C12 111.87(11) . . ? C17 C12 C13 120.71(13) . . ? C17 C12 C11 117.35(12) . . ? C13 C12 C11 121.92(12) . . ? C14 C13 C12 118.25(13) . . ? C14 C13 H13 120.9 . . ? C12 C13 H13 120.9 . . ? C15 C14 C13 123.25(13) . . ? C15 C14 N1 118.30(13) . . ? C13 C14 N1 118.43(13) . . ? C14 C15 C16 116.64(13) . . ? C14 C15 H15 121.7 . . ? C16 C15 H15 121.7 . . ? C17 C16 C15 122.95(13) . . ? C17 C16 N2 118.48(12) . . ? C15 C16 N2 118.55(12) . . ? C16 C17 C12 118.19(13) . . ? C16 C17 H17 120.9 . . ? C12 C17 H17 120.9 . . ? O3 N1 O4 123.88(13) . . ? O3 N1 C14 118.34(12) . . ? O4 N1 C14 117.77(13) . . ? O6 N2 O5 124.10(13) . . ? O6 N2 C16 118.26(12) . . ? O5 N2 C16 117.63(12) . . ? C11 O1 C1 116.15(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -69.11(14) . . . . ? C6 C1 C2 C3 50.10(16) . . . . ? C1 C2 C3 C4 -54.52(16) . . . . ? C2 C3 C4 C5 57.02(15) . . . . ? C2 C3 C4 C7 -174.60(11) . . . . ? C3 C4 C5 C6 -57.78(15) . . . . ? C7 C4 C5 C6 174.22(11) . . . . ? O1 C1 C6 C5 66.05(14) . . . . ? C2 C1 C6 C5 -50.80(16) . . . . ? C4 C5 C6 C1 56.02(15) . . . . ? C5 C4 C7 C8 58.97(16) . . . . ? C3 C4 C7 C8 -66.07(15) . . . . ? C5 C4 C7 C9 -179.98(12) . . . . ? C3 C4 C7 C9 54.98(15) . . . . ? C5 C4 C7 C10 -62.45(15) . . . . ? C3 C4 C7 C10 172.51(12) . . . . ? O2 C11 C12 C17 -5.11(19) . . . . ? O1 C11 C12 C17 174.85(11) . . . . ? O2 C11 C12 C13 175.97(12) . . . . ? O1 C11 C12 C13 -4.07(18) . . . . ? C17 C12 C13 C14 -0.04(19) . . . . ? C11 C12 C13 C14 178.85(11) . . . . ? C12 C13 C14 C15 -0.8(2) . . . . ? C12 C13 C14 N1 -179.19(11) . . . . ? C13 C14 C15 C16 0.7(2) . . . . ? N1 C14 C15 C16 179.10(11) . . . . ? C14 C15 C16 C17 0.23(19) . . . . ? C14 C15 C16 N2 -178.15(12) . . . . ? C15 C16 C17 C12 -1.0(2) . . . . ? N2 C16 C17 C12 177.40(11) . . . . ? C13 C12 C17 C16 0.87(19) . . . . ? C11 C12 C17 C16 -178.07(11) . . . . ? C15 C14 N1 O3 179.72(12) . . . . ? C13 C14 N1 O3 -1.77(18) . . . . ? C15 C14 N1 O4 0.81(18) . . . . ? C13 C14 N1 O4 179.32(12) . . . . ? C17 C16 N2 O6 -3.13(19) . . . . ? C15 C16 N2 O6 175.32(12) . . . . ? C17 C16 N2 O5 175.86(12) . . . . ? C15 C16 N2 O5 -5.70(19) . . . . ? O2 C11 O1 C1 3.29(19) . . . . ? C12 C11 O1 C1 -176.67(10) . . . . ? C2 C1 O1 C11 -161.16(11) . . . . ? C6 C1 O1 C11 78.23(14) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 65.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.251 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.041 data_compound4g _database_code_CSD 205441 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 55-57 _chemical_formula_moiety ? _chemical_formula_sum 'C12 H19 Cl3 O2' _chemical_formula_weight 301.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.6540(10) _cell_length_b 6.026(2) _cell_length_c 13.044(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.090(10) _cell_angle_gamma 90.00 _cell_volume 725.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 130.0(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 20 _cell_measurement_theta_max 30 _exptl_crystal_description needles _exptl_crystal_colour brown _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 5.630 _exptl_absorpt_correction_type Analytical _exptl_absorpt_correction_T_min 0.22 _exptl_absorpt_correction_T_max 0.67 _exptl_absorpt_process_details 'ABSORB Platon' _exptl_special_details ; ? ; _diffrn_ambient_temperature 130.0(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method \q2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 9600 _diffrn_standards_decay_% 2 _diffrn_reflns_number 1733 _diffrn_reflns_av_R_equivalents 0.0665 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 74.89 _reflns_number_total 1636 _reflns_number_gt 1589 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software 5.0 (Enraf-Nonius, 1989)' _computing_cell_refinement ? _computing_data_reduction 'PROCESS_DATA (Gable et al., 1994)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1044P)^2^+0.1497P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0082(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(2) _refine_ls_number_reflns 1636 _refine_ls_number_parameters 155 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0988 _refine_ls_wR_factor_gt 0.0966 _refine_ls_goodness_of_fit_ref 0.846 _refine_ls_restrained_S_all 0.845 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4610(3) 0.5887(6) 0.6742(2) 0.0248(6) Uani 1 1 d . . . H1 H 0.5461 0.5471 0.6493 0.030 Uiso 1 1 calc R . . C2 C 0.5061(3) 0.7565(6) 0.7639(2) 0.0271(7) Uani 1 1 d . . . H2A H 0.5360 0.8955 0.7359 0.033 Uiso 1 1 calc R . . H2B H 0.5907 0.6987 0.8206 0.033 Uiso 1 1 calc R . . C3 C 0.3835(3) 0.8073(6) 0.8126(2) 0.0247(6) Uani 1 1 d . . . H3A H 0.3040 0.8831 0.7583 0.030 Uiso 1 1 calc R . . H3B H 0.4198 0.9097 0.8740 0.030 Uiso 1 1 calc R . . C4 C 0.3239(3) 0.5978(5) 0.8510(2) 0.0195(5) Uani 1 1 d . . . H4 H 0.4070 0.5240 0.9045 0.023 Uiso 1 1 calc R . . C5 C 0.2724(3) 0.4397(6) 0.7556(2) 0.0240(6) Uani 1 1 d . . . H5A H 0.1913 0.5092 0.7000 0.029 Uiso 1 1 calc R . . H5B H 0.2359 0.3013 0.7794 0.029 Uiso 1 1 calc R . . C6 C 0.3943(4) 0.3829(6) 0.7068(2) 0.0277(7) Uani 1 1 d . . . H6A H 0.4704 0.2980 0.7597 0.033 Uiso 1 1 calc R . . H6B H 0.3552 0.2874 0.6430 0.033 Uiso 1 1 calc R . . C7 C 0.2069(3) 0.6479(6) 0.9090(2) 0.0257(7) Uani 1 1 d . . . C8 C 0.2741(4) 0.7906(8) 1.0083(2) 0.0367(8) Uani 1 1 d . . . H8A H 0.3076 0.9314 0.9864 0.055 Uiso 1 1 calc R . . H8B H 0.3564 0.7116 1.0566 0.055 Uiso 1 1 calc R . . H8C H 0.2013 0.8201 1.0455 0.055 Uiso 1 1 calc R . . C9 C 0.0749(3) 0.7682(8) 0.8359(2) 0.0344(8) Uani 1 1 d . . . H9A H 0.1061 0.9071 0.8104 0.052 Uiso 1 1 calc R . . H9B H 0.0061 0.8011 0.8761 0.052 Uiso 1 1 calc R . . H9C H 0.0280 0.6735 0.7744 0.052 Uiso 1 1 calc R . . C10 C 0.1571(5) 0.4319(9) 0.9470(3) 0.0449(9) Uani 1 1 d . . . H10A H 0.1118 0.3377 0.8850 0.067 Uiso 1 1 calc R . . H10B H 0.0867 0.4641 0.9860 0.067 Uiso 1 1 calc R . . H10C H 0.2408 0.3546 0.9947 0.067 Uiso 1 1 calc R . . C11 C 0.3399(3) 0.6335(6) 0.4883(2) 0.0210(6) Uani 1 1 d . . . C12 C 0.2059(3) 0.7458(5) 0.4085(2) 0.0218(6) Uani 1 1 d . . . O1 O 0.3496(2) 0.6996(4) 0.58677(15) 0.0228(4) Uani 1 1 d . . . O2 O 0.4139(2) 0.5019(5) 0.46062(17) 0.0313(5) Uani 1 1 d . . . Cl1 Cl 0.20147(8) 1.03268(12) 0.43233(6) 0.0273(2) Uani 1 1 d . . . Cl2 Cl 0.20956(8) 0.70131(15) 0.27572(5) 0.0309(2) Uani 1 1 d . . . Cl3 Cl 0.05085(7) 0.61547(15) 0.42818(6) 0.0311(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0203(12) 0.0308(18) 0.0212(13) 0.0032(13) 0.0028(10) 0.0075(12) C2 0.0224(13) 0.0339(18) 0.0246(13) 0.0007(13) 0.0063(11) -0.0056(13) C3 0.0295(15) 0.0205(14) 0.0230(13) -0.0043(12) 0.0061(11) -0.0048(12) C4 0.0211(12) 0.0187(13) 0.0164(11) 0.0004(11) 0.0018(9) -0.0012(11) C5 0.0301(14) 0.0187(13) 0.0212(13) 0.0002(12) 0.0044(11) -0.0037(13) C6 0.0360(16) 0.0206(14) 0.0250(14) 0.0005(12) 0.0066(13) 0.0070(13) C7 0.0227(13) 0.0336(18) 0.0201(13) 0.0022(13) 0.0053(11) -0.0002(13) C8 0.0373(17) 0.050(2) 0.0216(14) -0.0078(16) 0.0067(13) 0.0033(17) C9 0.0247(14) 0.051(2) 0.0259(14) -0.0005(15) 0.0050(12) 0.0093(15) C10 0.047(2) 0.050(2) 0.0435(18) 0.009(2) 0.0227(16) -0.008(2) C11 0.0199(12) 0.0229(14) 0.0198(12) -0.0006(11) 0.0052(10) -0.0009(12) C12 0.0167(12) 0.0252(16) 0.0219(13) -0.0007(12) 0.0030(10) -0.0003(11) O1 0.0221(9) 0.0284(11) 0.0173(8) 0.0015(9) 0.0049(7) 0.0056(9) O2 0.0293(11) 0.0372(14) 0.0265(10) -0.0028(11) 0.0067(8) 0.0121(11) Cl1 0.0292(4) 0.0220(3) 0.0284(3) 0.0019(3) 0.0049(3) 0.0035(3) Cl2 0.0295(4) 0.0433(5) 0.0185(3) -0.0019(3) 0.0050(2) 0.0009(3) Cl3 0.0207(3) 0.0374(4) 0.0358(4) 0.0020(3) 0.0094(3) -0.0059(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.478(3) . ? C1 C2 1.510(4) . ? C1 C6 1.515(5) . ? C1 H1 1.0000 . ? C2 C3 1.529(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.531(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.529(4) . ? C4 C7 1.562(4) . ? C4 H4 1.0000 . ? C5 C6 1.532(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C10 1.520(5) . ? C7 C9 1.531(4) . ? C7 C8 1.532(4) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 O2 1.192(4) . ? C11 O1 1.321(3) . ? C11 C12 1.557(4) . ? C12 Cl1 1.759(3) . ? C12 Cl2 1.763(3) . ? C12 Cl3 1.775(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 105.9(3) . . ? O1 C1 C6 108.3(2) . . ? C2 C1 C6 112.4(2) . . ? O1 C1 H1 110.1 . . ? C2 C1 H1 110.1 . . ? C6 C1 H1 110.1 . . ? C1 C2 C3 111.9(2) . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C2 C3 C4 112.5(3) . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C3 108.1(2) . . ? C5 C4 C7 114.0(2) . . ? C3 C4 C7 113.2(3) . . ? C5 C4 H4 107.1 . . ? C3 C4 H4 107.1 . . ? C7 C4 H4 107.1 . . ? C4 C5 C6 111.8(2) . . ? C4 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? C4 C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 107.9 . . ? C1 C6 C5 112.0(3) . . ? C1 C6 H6A 109.2 . . ? C5 C6 H6A 109.2 . . ? C1 C6 H6B 109.2 . . ? C5 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C10 C7 C9 108.9(3) . . ? C10 C7 C8 107.5(3) . . ? C9 C7 C8 109.2(3) . . ? C10 C7 C4 109.6(3) . . ? C9 C7 C4 112.2(2) . . ? C8 C7 C4 109.4(2) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O2 C11 O1 128.1(3) . . ? O2 C11 C12 122.7(3) . . ? O1 C11 C12 109.1(2) . . ? C11 C12 Cl1 111.6(2) . . ? C11 C12 Cl2 109.8(2) . . ? Cl1 C12 Cl2 109.37(17) . . ? C11 C12 Cl3 106.3(2) . . ? Cl1 C12 Cl3 110.11(17) . . ? Cl2 C12 Cl3 109.64(16) . . ? C11 O1 C1 116.2(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 67.0(3) . . . . ? C6 C1 C2 C3 -51.0(4) . . . . ? C1 C2 C3 C4 55.0(3) . . . . ? C2 C3 C4 C5 -57.2(3) . . . . ? C2 C3 C4 C7 175.5(2) . . . . ? C3 C4 C5 C6 57.4(3) . . . . ? C7 C4 C5 C6 -175.8(3) . . . . ? O1 C1 C6 C5 -65.0(3) . . . . ? C2 C1 C6 C5 51.6(3) . . . . ? C4 C5 C6 C1 -55.7(3) . . . . ? C5 C4 C7 C10 57.5(3) . . . . ? C3 C4 C7 C10 -178.4(3) . . . . ? C5 C4 C7 C9 -63.6(4) . . . . ? C3 C4 C7 C9 60.5(3) . . . . ? C5 C4 C7 C8 175.1(3) . . . . ? C3 C4 C7 C8 -60.8(3) . . . . ? O2 C11 C12 Cl1 -135.3(3) . . . . ? O1 C11 C12 Cl1 47.9(3) . . . . ? O2 C11 C12 Cl2 -13.9(4) . . . . ? O1 C11 C12 Cl2 169.3(2) . . . . ? O2 C11 C12 Cl3 104.6(3) . . . . ? O1 C11 C12 Cl3 -72.2(3) . . . . ? O2 C11 O1 C1 -3.5(5) . . . . ? C12 C11 O1 C1 173.1(2) . . . . ? C2 C1 O1 C11 151.1(3) . . . . ? C6 C1 O1 C11 -88.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 74.89 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.761 _refine_diff_density_min -0.406 _refine_diff_density_rms 0.077 data_compound4h _database_code_CSD 205442 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H22 Cl N O4' _chemical_formula_weight 339.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.9757(3) _cell_length_b 36.6182(8) _cell_length_c 7.0342(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.5550(10) _cell_angle_gamma 90.00 _cell_volume 1713.12(10) _cell_formula_units_Z 4 _cell_measurement_temperature 130.0(2) _cell_measurement_reflns_used 25460 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.242 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130.0(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _diffrn_measurement_method CCD _diffrn_standards_decay_% ? _diffrn_reflns_number 10738 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_sigmaI/netI 0.0624 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -43 _diffrn_reflns_limit_k_max 43 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2860 _reflns_number_gt 1991 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0412P)^2^+0.0407P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2860 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0770 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.0947 _refine_ls_wR_factor_gt 0.0865 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1205(3) -0.12455(6) 0.5856(3) 0.0300(5) Uani 1 1 d . . . H1 H -0.0012 -0.1167 0.4765 0.036 Uiso 1 1 calc R . . C2 C 0.2394(3) -0.15216(6) 0.5072(3) 0.0327(6) Uani 1 1 d . . . H2A H 0.2887 -0.1404 0.4040 0.039 Uiso 1 1 calc R . . H2B H 0.1496 -0.1725 0.4434 0.039 Uiso 1 1 calc R . . C3 C 0.4177(3) -0.16739(6) 0.6708(3) 0.0291(5) Uani 1 1 d . . . H3A H 0.5160 -0.1476 0.7234 0.035 Uiso 1 1 calc R . . H3B H 0.4850 -0.1864 0.6136 0.035 Uiso 1 1 calc R . . C4 C 0.3529(3) -0.18393(6) 0.8424(3) 0.0267(5) Uani 1 1 d . . . H4 H 0.2529 -0.2034 0.7815 0.032 Uiso 1 1 calc R . . C5 C 0.2388(3) -0.15516(6) 0.9230(3) 0.0311(5) Uani 1 1 d . . . H5A H 0.3318 -0.1350 0.9840 0.037 Uiso 1 1 calc R . . H5B H 0.1906 -0.1663 1.0285 0.037 Uiso 1 1 calc R . . C6 C 0.0593(3) -0.13958(6) 0.7602(3) 0.0325(6) Uani 1 1 d . . . H6A H -0.0424 -0.1590 0.7118 0.039 Uiso 1 1 calc R . . H6B H -0.0031 -0.1198 0.8174 0.039 Uiso 1 1 calc R . . C7 C 0.5263(3) -0.20321(6) 1.0053(3) 0.0321(6) Uani 1 1 d . . . C8 C 0.6818(4) -0.17579(7) 1.1244(4) 0.0525(7) Uani 1 1 d . . . H8A H 0.6151 -0.1575 1.1845 0.079 Uiso 1 1 calc R . . H8B H 0.7459 -0.1636 1.0353 0.079 Uiso 1 1 calc R . . H8C H 0.7841 -0.1886 1.2297 0.079 Uiso 1 1 calc R . . C9 C 0.6314(4) -0.23113(7) 0.9103(3) 0.0447(7) Uani 1 1 d . . . H9A H 0.5323 -0.2486 0.8321 0.067 Uiso 1 1 calc R . . H9B H 0.7334 -0.2442 1.0150 0.067 Uiso 1 1 calc R . . H9C H 0.6959 -0.2186 0.8228 0.067 Uiso 1 1 calc R . . C10 C 0.4366(4) -0.22384(7) 1.1491(4) 0.0513(7) Uani 1 1 d . . . H10A H 0.3669 -0.2066 1.2116 0.077 Uiso 1 1 calc R . . H10B H 0.5448 -0.2359 1.2523 0.077 Uiso 1 1 calc R . . H10C H 0.3411 -0.2422 1.0749 0.077 Uiso 1 1 calc R . . C11 C 0.1780(3) -0.06046(6) 0.6520(3) 0.0248(5) Uani 1 1 d . . . C12 C 0.3361(3) -0.03180(6) 0.7033(3) 0.0226(5) Uani 1 1 d . . . C13 C 0.2788(3) 0.00446(6) 0.7147(3) 0.0231(5) Uani 1 1 d . . . H13 H 0.1420 0.0104 0.6974 0.028 Uiso 1 1 calc R . . C14 C 0.4220(3) 0.03158(6) 0.7510(3) 0.0225(5) Uani 1 1 d . . . C15 C 0.6244(3) 0.02350(6) 0.7836(3) 0.0244(5) Uani 1 1 d . . . C16 C 0.6816(3) -0.01239(6) 0.7762(3) 0.0278(5) Uani 1 1 d . . . H16 H 0.8196 -0.0182 0.8006 0.033 Uiso 1 1 calc R . . C17 C 0.5387(3) -0.04007(6) 0.7334(3) 0.0265(5) Uani 1 1 d . . . H17 H 0.5788 -0.0646 0.7245 0.032 Uiso 1 1 calc R . . N1 N 0.3542(3) 0.06959(5) 0.7486(3) 0.0275(4) Uani 1 1 d . . . O1 O 0.2572(2) -0.09358(4) 0.6530(2) 0.0284(4) Uani 1 1 d . . . O2 O -0.0009(2) -0.05414(4) 0.6107(2) 0.0301(4) Uani 1 1 d . . . O3 O 0.2371(2) 0.07688(4) 0.8439(2) 0.0340(4) Uani 1 1 d . . . O4 O 0.4141(2) 0.09179(4) 0.6487(2) 0.0368(4) Uani 1 1 d . . . Cl1 Cl 0.80951(8) 0.056615(16) 0.84170(8) 0.03503(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0289(12) 0.0244(14) 0.0309(13) -0.0015(11) 0.0001(10) 0.0013(10) C2 0.0433(14) 0.0271(14) 0.0271(13) -0.0007(11) 0.0097(10) 0.0037(11) C3 0.0339(13) 0.0245(13) 0.0311(13) 0.0002(11) 0.0129(10) 0.0055(10) C4 0.0297(12) 0.0195(13) 0.0283(12) -0.0029(10) 0.0049(9) -0.0032(9) C5 0.0374(13) 0.0256(13) 0.0328(13) 0.0023(11) 0.0145(10) 0.0005(11) C6 0.0297(13) 0.0255(14) 0.0431(14) -0.0010(12) 0.0124(11) 0.0024(10) C7 0.0376(13) 0.0255(13) 0.0304(13) 0.0014(11) 0.0060(10) 0.0040(11) C8 0.0456(16) 0.0382(17) 0.0553(17) -0.0042(14) -0.0126(13) 0.0058(13) C9 0.0487(16) 0.0373(16) 0.0417(15) 0.0022(12) 0.0040(12) 0.0168(12) C10 0.0646(19) 0.0483(18) 0.0398(15) 0.0159(13) 0.0140(13) 0.0150(14) C11 0.0306(13) 0.0255(14) 0.0177(11) 0.0008(10) 0.0065(9) 0.0075(11) C12 0.0271(12) 0.0242(13) 0.0165(11) 0.0002(10) 0.0064(9) 0.0031(10) C13 0.0244(11) 0.0284(14) 0.0173(11) 0.0019(10) 0.0075(9) 0.0045(10) C14 0.0265(12) 0.0216(12) 0.0199(12) 0.0018(10) 0.0076(9) 0.0034(10) C15 0.0262(12) 0.0311(14) 0.0159(11) -0.0015(10) 0.0062(9) -0.0035(10) C16 0.0253(12) 0.0358(15) 0.0230(12) -0.0002(11) 0.0083(9) 0.0039(10) C17 0.0325(13) 0.0275(14) 0.0206(12) -0.0005(10) 0.0094(9) 0.0051(10) N1 0.0264(10) 0.0268(12) 0.0270(11) -0.0026(10) 0.0046(8) -0.0019(9) O1 0.0283(8) 0.0196(9) 0.0359(9) 0.0002(7) 0.0077(7) 0.0026(7) O2 0.0266(9) 0.0265(9) 0.0351(9) -0.0013(7) 0.0064(7) 0.0035(7) O3 0.0328(9) 0.0343(10) 0.0381(9) -0.0032(8) 0.0156(7) 0.0042(7) O4 0.0413(10) 0.0272(10) 0.0443(10) 0.0058(8) 0.0166(8) -0.0040(8) Cl1 0.0274(3) 0.0401(4) 0.0367(4) -0.0024(3) 0.0082(2) -0.0066(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.466(2) . ? C1 C2 1.513(3) . ? C1 C6 1.520(3) . ? C1 H1 1.0000 . ? C2 C3 1.523(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.536(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.529(3) . ? C4 C7 1.562(3) . ? C4 H4 1.0000 . ? C5 C6 1.530(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C9 1.524(3) . ? C7 C8 1.529(3) . ? C7 C10 1.539(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 O2 1.215(2) . ? C11 O1 1.332(2) . ? C11 C12 1.486(3) . ? C12 C13 1.396(3) . ? C12 C17 1.398(3) . ? C13 C14 1.377(3) . ? C13 H13 0.9500 . ? C14 C15 1.392(3) . ? C14 N1 1.468(3) . ? C15 C16 1.379(3) . ? C15 Cl1 1.728(2) . ? C16 C17 1.389(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? N1 O4 1.227(2) . ? N1 O3 1.232(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 105.08(17) . . ? O1 C1 C6 109.45(16) . . ? C2 C1 C6 111.76(18) . . ? O1 C1 H1 110.1 . . ? C2 C1 H1 110.1 . . ? C6 C1 H1 110.1 . . ? C1 C2 C3 112.45(18) . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2B 109.1 . . ? C3 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C4 111.78(17) . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 107.9 . . ? C5 C4 C3 109.24(17) . . ? C5 C4 C7 114.47(16) . . ? C3 C4 C7 114.10(17) . . ? C5 C4 H4 106.1 . . ? C3 C4 H4 106.1 . . ? C7 C4 H4 106.1 . . ? C4 C5 C6 112.30(18) . . ? C4 C5 H5A 109.1 . . ? C6 C5 H5A 109.1 . . ? C4 C5 H5B 109.1 . . ? C6 C5 H5B 109.1 . . ? H5A C5 H5B 107.9 . . ? C1 C6 C5 111.98(17) . . ? C1 C6 H6A 109.2 . . ? C5 C6 H6A 109.2 . . ? C1 C6 H6B 109.2 . . ? C5 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C9 C7 C8 108.99(19) . . ? C9 C7 C10 107.7(2) . . ? C8 C7 C10 108.91(18) . . ? C9 C7 C4 110.50(17) . . ? C8 C7 C4 111.69(19) . . ? C10 C7 C4 109.00(18) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O2 C11 O1 124.7(2) . . ? O2 C11 C12 123.9(2) . . ? O1 C11 C12 111.43(17) . . ? C13 C12 C17 119.4(2) . . ? C13 C12 C11 118.78(18) . . ? C17 C12 C11 121.75(19) . . ? C14 C13 C12 119.50(19) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C13 C14 C15 121.4(2) . . ? C13 C14 N1 117.92(18) . . ? C15 C14 N1 120.69(19) . . ? C16 C15 C14 119.13(19) . . ? C16 C15 Cl1 118.28(16) . . ? C14 C15 Cl1 122.55(17) . . ? C15 C16 C17 120.46(19) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C16 C17 C12 120.1(2) . . ? C16 C17 H17 120.0 . . ? C12 C17 H17 120.0 . . ? O4 N1 O3 124.30(18) . . ? O4 N1 C14 118.09(17) . . ? O3 N1 C14 117.59(17) . . ? C11 O1 C1 118.31(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 65.9(2) . . . . ? C6 C1 C2 C3 -52.7(2) . . . . ? C1 C2 C3 C4 55.3(2) . . . . ? C2 C3 C4 C5 -55.8(2) . . . . ? C2 C3 C4 C7 174.62(18) . . . . ? C3 C4 C5 C6 55.7(2) . . . . ? C7 C4 C5 C6 -174.94(17) . . . . ? O1 C1 C6 C5 -63.9(2) . . . . ? C2 C1 C6 C5 52.0(2) . . . . ? C4 C5 C6 C1 -54.6(2) . . . . ? C5 C4 C7 C9 -179.65(19) . . . . ? C3 C4 C7 C9 -52.8(2) . . . . ? C5 C4 C7 C8 -58.1(2) . . . . ? C3 C4 C7 C8 68.7(2) . . . . ? C5 C4 C7 C10 62.2(2) . . . . ? C3 C4 C7 C10 -170.87(19) . . . . ? O2 C11 C12 C13 3.2(3) . . . . ? O1 C11 C12 C13 -178.13(16) . . . . ? O2 C11 C12 C17 -174.55(18) . . . . ? O1 C11 C12 C17 4.1(3) . . . . ? C17 C12 C13 C14 1.4(3) . . . . ? C11 C12 C13 C14 -176.39(17) . . . . ? C12 C13 C14 C15 -2.2(3) . . . . ? C12 C13 C14 N1 175.96(17) . . . . ? C13 C14 C15 C16 0.9(3) . . . . ? N1 C14 C15 C16 -177.18(18) . . . . ? C13 C14 C15 Cl1 -176.75(15) . . . . ? N1 C14 C15 Cl1 5.1(3) . . . . ? C14 C15 C16 C17 1.2(3) . . . . ? Cl1 C15 C16 C17 178.95(14) . . . . ? C15 C16 C17 C12 -2.0(3) . . . . ? C13 C12 C17 C16 0.7(3) . . . . ? C11 C12 C17 C16 178.38(17) . . . . ? C13 C14 N1 O4 -130.31(19) . . . . ? C15 C14 N1 O4 47.9(2) . . . . ? C13 C14 N1 O3 48.2(2) . . . . ? C15 C14 N1 O3 -133.66(18) . . . . ? O2 C11 O1 C1 4.8(3) . . . . ? C12 C11 O1 C1 -173.86(15) . . . . ? C2 C1 O1 C11 152.66(16) . . . . ? C6 C1 O1 C11 -87.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.224 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.046 data_compound4i _database_code_CSD 205443 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 80-83 _chemical_formula_moiety ? _chemical_formula_sum 'C16 H23 N O3' _chemical_formula_weight 277.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.179(2) _cell_length_b 11.071(3) _cell_length_c 11.130(2) _cell_angle_alpha 100.57(2) _cell_angle_beta 90.17(2) _cell_angle_gamma 95.16(2) _cell_volume 745.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 130.0(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 15 _exptl_crystal_description plates _exptl_crystal_colour yellow _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130.0(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method \q2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 9600 _diffrn_standards_decay_% 2 _diffrn_reflns_number 2888 _diffrn_reflns_av_R_equivalents 0.0196 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 24.97 _reflns_number_total 2622 _reflns_number_gt 2196 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software 5.0 (Enraf-Nonius, 1989)' _computing_cell_refinement ? _computing_data_reduction 'PROCESS_DATA (Gable et al., 1994)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0785P)^2^+0.2995P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.011(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2622 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1332 _refine_ls_wR_factor_gt 0.1252 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3865(3) 0.07958(15) 0.85672(14) 0.0234(4) Uani 1 1 d . . . H1 H 0.4509 0.1144 0.9397 0.028 Uiso 1 1 calc R . . C2 C 0.1834(3) -0.00456(16) 0.86885(15) 0.0275(4) Uani 1 1 d . . . H2A H 0.0708 0.0457 0.9098 0.033 Uiso 1 1 calc R . . H2B H 0.2174 -0.0636 0.9215 0.033 Uiso 1 1 calc R . . C3 C 0.0918(3) -0.07673(15) 0.74619(15) 0.0241(4) Uani 1 1 d . . . H3A H 0.0425 -0.0185 0.6965 0.029 Uiso 1 1 calc R . . H3B H -0.0358 -0.1328 0.7605 0.029 Uiso 1 1 calc R . . C4 C 0.2623(2) -0.15245(14) 0.67575(14) 0.0205(4) Uani 1 1 d . . . H4 H 0.3132 -0.2067 0.7306 0.025 Uiso 1 1 calc R . . C5 C 0.4576(3) -0.06245(15) 0.65725(14) 0.0234(4) Uani 1 1 d . . . H5A H 0.5711 -0.1093 0.6126 0.028 Uiso 1 1 calc R . . H5B H 0.4115 -0.0043 0.6065 0.028 Uiso 1 1 calc R . . C6 C 0.5537(3) 0.01078(15) 0.77855(15) 0.0227(4) Uani 1 1 d . . . H6A H 0.6164 -0.0465 0.8248 0.027 Uiso 1 1 calc R . . H6B H 0.6731 0.0708 0.7616 0.027 Uiso 1 1 calc R . . C7 C 0.1731(3) -0.23881(15) 0.55625(15) 0.0243(4) Uani 1 1 d . . . C8 C 0.3532(3) -0.31444(18) 0.49629(17) 0.0362(5) Uani 1 1 d . . . H8A H 0.4094 -0.3612 0.5544 0.054 Uiso 1 1 calc R . . H8B H 0.4712 -0.2588 0.4727 0.054 Uiso 1 1 calc R . . H8C H 0.2941 -0.3717 0.4235 0.054 Uiso 1 1 calc R . . C9 C 0.0866(3) -0.16610(18) 0.46449(16) 0.0340(4) Uani 1 1 d . . . H9A H 0.2031 -0.1074 0.4445 0.051 Uiso 1 1 calc R . . H9B H -0.0342 -0.1211 0.5005 0.051 Uiso 1 1 calc R . . H9C H 0.0355 -0.2233 0.3899 0.051 Uiso 1 1 calc R . . C10 C -0.0119(3) -0.32990(17) 0.58622(17) 0.0314(4) Uani 1 1 d . . . H10A H 0.0411 -0.3771 0.6448 0.047 Uiso 1 1 calc R . . H10B H -0.0627 -0.3865 0.5112 0.047 Uiso 1 1 calc R . . H10C H -0.1322 -0.2843 0.6218 0.047 Uiso 1 1 calc R . . C11 C 0.4309(3) 0.29030(15) 0.82239(14) 0.0217(4) Uani 1 1 d . . . C12 C 0.6414(3) 0.31271(15) 0.87319(15) 0.0247(4) Uani 1 1 d . . . H12 H 0.7123 0.2474 0.8960 0.030 Uiso 1 1 calc R . . C13 C 0.7453(3) 0.43071(16) 0.89000(15) 0.0250(4) Uani 1 1 d . . . H13 H 0.8885 0.4466 0.9240 0.030 Uiso 1 1 calc R . . C14 C 0.6412(3) 0.52519(15) 0.85750(14) 0.0222(4) Uani 1 1 d . . . C15 C 0.4310(3) 0.50498(15) 0.80790(14) 0.0247(4) Uani 1 1 d . . . H15 H 0.3594 0.5712 0.7877 0.030 Uiso 1 1 calc R . . C16 C 0.3292(3) 0.38710(16) 0.78880(15) 0.0245(4) Uani 1 1 d . . . H16 H 0.1879 0.3714 0.7523 0.029 Uiso 1 1 calc R . . N1 N 0.7489(2) 0.65006(13) 0.88015(12) 0.0262(4) Uani 1 1 d . . . O1 O 0.31333(18) 0.17921(10) 0.80173(10) 0.0250(3) Uani 1 1 d . . . O2 O 0.6475(2) 0.73451(11) 0.85959(12) 0.0343(3) Uani 1 1 d . . . O3 O 0.9383(2) 0.66542(12) 0.91877(13) 0.0389(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0276(9) 0.0239(8) 0.0193(8) 0.0052(6) -0.0015(6) 0.0031(7) C2 0.0302(9) 0.0297(9) 0.0235(9) 0.0069(7) 0.0080(7) 0.0024(7) C3 0.0189(8) 0.0250(8) 0.0293(9) 0.0074(7) 0.0058(7) 0.0011(6) C4 0.0184(8) 0.0229(8) 0.0214(8) 0.0067(6) 0.0003(6) 0.0031(6) C5 0.0202(8) 0.0264(8) 0.0234(8) 0.0044(7) 0.0039(6) 0.0022(7) C6 0.0190(8) 0.0231(8) 0.0263(9) 0.0056(7) -0.0012(6) 0.0015(6) C7 0.0230(8) 0.0259(9) 0.0237(8) 0.0044(7) -0.0009(7) 0.0011(7) C8 0.0337(10) 0.0379(11) 0.0317(10) -0.0071(8) 0.0022(8) 0.0022(8) C9 0.0384(10) 0.0355(10) 0.0275(9) 0.0077(8) -0.0102(8) -0.0044(8) C10 0.0297(9) 0.0289(9) 0.0341(10) 0.0050(7) -0.0037(7) -0.0039(7) C11 0.0238(8) 0.0234(8) 0.0171(7) 0.0013(6) 0.0007(6) 0.0032(6) C12 0.0261(9) 0.0255(9) 0.0232(8) 0.0043(7) -0.0049(7) 0.0059(7) C13 0.0221(8) 0.0307(9) 0.0218(8) 0.0050(7) -0.0045(6) 0.0005(7) C14 0.0252(8) 0.0243(8) 0.0171(8) 0.0043(6) 0.0005(6) 0.0015(7) C15 0.0266(9) 0.0266(9) 0.0226(8) 0.0066(7) -0.0003(7) 0.0071(7) C16 0.0212(8) 0.0293(9) 0.0229(8) 0.0033(7) -0.0034(6) 0.0039(7) N1 0.0283(8) 0.0288(8) 0.0224(7) 0.0083(6) -0.0014(6) -0.0007(6) O1 0.0239(6) 0.0225(6) 0.0284(6) 0.0047(5) -0.0043(5) 0.0017(5) O2 0.0358(7) 0.0265(7) 0.0438(8) 0.0142(6) -0.0018(6) 0.0048(6) O3 0.0330(8) 0.0352(7) 0.0488(8) 0.0132(6) -0.0150(6) -0.0062(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.460(2) . ? C1 C2 1.516(2) . ? C1 C6 1.520(2) . ? C1 H1 1.0000 . ? C2 C3 1.529(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.533(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.534(2) . ? C4 C7 1.556(2) . ? C4 H4 1.0000 . ? C5 C6 1.530(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C9 1.534(2) . ? C7 C10 1.534(2) . ? C7 C8 1.534(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 O1 1.352(2) . ? C11 C16 1.396(2) . ? C11 C12 1.399(2) . ? C12 C13 1.383(2) . ? C12 H12 0.9500 . ? C13 C14 1.377(2) . ? C13 H13 0.9500 . ? C14 C15 1.393(2) . ? C14 N1 1.457(2) . ? C15 C16 1.376(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N1 O2 1.2257(19) . ? N1 O3 1.232(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 105.47(13) . . ? O1 C1 C6 111.61(13) . . ? C2 C1 C6 111.33(14) . . ? O1 C1 H1 109.5 . . ? C2 C1 H1 109.5 . . ? C6 C1 H1 109.5 . . ? C1 C2 C3 113.25(13) . . ? C1 C2 H2A 108.9 . . ? C3 C2 H2A 108.9 . . ? C1 C2 H2B 108.9 . . ? C3 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? C2 C3 C4 111.39(14) . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? C3 C4 C5 107.57(13) . . ? C3 C4 C7 114.09(13) . . ? C5 C4 C7 114.23(13) . . ? C3 C4 H4 106.8 . . ? C5 C4 H4 106.8 . . ? C7 C4 H4 106.8 . . ? C6 C5 C4 112.16(13) . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5B 109.2 . . ? C4 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C1 C6 C5 112.72(13) . . ? C1 C6 H6A 109.0 . . ? C5 C6 H6A 109.0 . . ? C1 C6 H6B 109.0 . . ? C5 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C9 C7 C10 108.54(14) . . ? C9 C7 C8 108.97(15) . . ? C10 C7 C8 107.59(15) . . ? C9 C7 C4 111.92(14) . . ? C10 C7 C4 109.85(13) . . ? C8 C7 C4 109.87(13) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O1 C11 C16 115.58(14) . . ? O1 C11 C12 124.80(15) . . ? C16 C11 C12 119.61(15) . . ? C13 C12 C11 119.47(15) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C14 C13 C12 120.02(15) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 121.37(15) . . ? C13 C14 N1 119.52(15) . . ? C15 C14 N1 119.05(15) . . ? C16 C15 C14 118.63(15) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C15 C16 C11 120.86(15) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? O2 N1 O3 123.19(15) . . ? O2 N1 C14 118.62(14) . . ? O3 N1 C14 118.19(14) . . ? C11 O1 C1 119.05(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 70.72(17) . . . . ? C6 C1 C2 C3 -50.49(19) . . . . ? C1 C2 C3 C4 56.24(19) . . . . ? C2 C3 C4 C5 -58.25(17) . . . . ? C2 C3 C4 C7 173.94(13) . . . . ? C3 C4 C5 C6 58.23(17) . . . . ? C7 C4 C5 C6 -174.04(13) . . . . ? O1 C1 C6 C5 -67.81(17) . . . . ? C2 C1 C6 C5 49.75(18) . . . . ? C4 C5 C6 C1 -55.38(18) . . . . ? C3 C4 C7 C9 61.46(18) . . . . ? C5 C4 C7 C9 -62.86(18) . . . . ? C3 C4 C7 C10 -59.18(18) . . . . ? C5 C4 C7 C10 176.50(13) . . . . ? C3 C4 C7 C8 -177.35(14) . . . . ? C5 C4 C7 C8 58.33(18) . . . . ? O1 C11 C12 C13 -179.95(14) . . . . ? C16 C11 C12 C13 0.3(2) . . . . ? C11 C12 C13 C14 0.4(2) . . . . ? C12 C13 C14 C15 0.2(2) . . . . ? C12 C13 C14 N1 177.55(14) . . . . ? C13 C14 C15 C16 -1.6(2) . . . . ? N1 C14 C15 C16 -178.88(14) . . . . ? C14 C15 C16 C11 2.3(2) . . . . ? O1 C11 C16 C15 178.57(14) . . . . ? C12 C11 C16 C15 -1.7(2) . . . . ? C13 C14 N1 O2 -174.33(14) . . . . ? C15 C14 N1 O2 3.0(2) . . . . ? C13 C14 N1 O3 5.9(2) . . . . ? C15 C14 N1 O3 -176.73(14) . . . . ? C16 C11 O1 C1 -167.24(13) . . . . ? C12 C11 O1 C1 13.0(2) . . . . ? C2 C1 O1 C11 154.01(13) . . . . ? C6 C1 O1 C11 -84.96(16) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.273 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.045 data_compound5e _database_code_CSD 205444 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 88-90 _chemical_formula_moiety ? _chemical_formula_sum 'C17 H23 N O4' _chemical_formula_weight 305.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.23700(10) _cell_length_b 12.7728(2) _cell_length_c 20.4391(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.7220(10) _cell_angle_gamma 90.00 _cell_volume 1613.49(5) _cell_formula_units_Z 4 _cell_measurement_temperature 130.0(2) _cell_measurement_reflns_used 18573 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _diffrn_measurement_method CCD _diffrn_standards_decay_% ? _diffrn_reflns_number 16946 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0421 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 28.49 _reflns_number_total 3719 _reflns_number_gt 2826 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0328P)^2^+0.7320P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3719 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0697 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1033 _refine_ls_wR_factor_gt 0.0943 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2274(2) 0.49331(11) 0.13064(7) 0.0226(3) Uani 1 1 d . . . H1 H 0.3004 0.4725 0.1753 0.027 Uiso 1 1 calc R . . C2 C 0.3870(2) 0.49077(11) 0.08168(7) 0.0257(3) Uani 1 1 d . . . H2A H 0.5121 0.5362 0.0972 0.031 Uiso 1 1 calc R . . H2B H 0.3178 0.5177 0.0385 0.031 Uiso 1 1 calc R . . C3 C 0.4642(2) 0.37838(11) 0.07381(7) 0.0243(3) Uani 1 1 d . . . H3A H 0.5379 0.3529 0.1168 0.029 Uiso 1 1 calc R . . H3B H 0.5703 0.3773 0.0419 0.029 Uiso 1 1 calc R . . C4 C 0.2751(2) 0.30484(11) 0.04952(7) 0.0228(3) Uani 1 1 d . . . H4 H 0.2001 0.3351 0.0075 0.027 Uiso 1 1 calc R . . C5 C 0.1153(2) 0.30891(12) 0.09959(8) 0.0278(3) Uani 1 1 d . . . H5A H 0.1851 0.2809 0.1424 0.033 Uiso 1 1 calc R . . H5B H -0.0109 0.2641 0.0842 0.033 Uiso 1 1 calc R . . C6 C 0.0378(2) 0.42107(12) 0.10943(8) 0.0280(3) Uani 1 1 d . . . H6A H -0.0435 0.4470 0.0676 0.034 Uiso 1 1 calc R . . H6B H -0.0611 0.4214 0.1435 0.034 Uiso 1 1 calc R . . C7 C 0.3493(2) 0.19269(12) 0.03329(7) 0.0252(3) Uani 1 1 d . . . C8 C 0.4714(3) 0.19770(13) -0.02658(8) 0.0355(4) Uani 1 1 d . . . H8A H 0.5989 0.2427 -0.0165 0.053 Uiso 1 1 calc R . . H8B H 0.3764 0.2265 -0.0644 0.053 Uiso 1 1 calc R . . H8C H 0.5174 0.1271 -0.0373 0.053 Uiso 1 1 calc R . . C9 C 0.4979(3) 0.14311(12) 0.09171(8) 0.0307(4) Uani 1 1 d . . . H9A H 0.6238 0.1883 0.1040 0.046 Uiso 1 1 calc R . . H9B H 0.5464 0.0741 0.0787 0.046 Uiso 1 1 calc R . . H9C H 0.4177 0.1355 0.1295 0.046 Uiso 1 1 calc R . . C10 C 0.1507(3) 0.12173(13) 0.01438(9) 0.0357(4) Uani 1 1 d . . . H10A H 0.0677 0.1168 0.0517 0.054 Uiso 1 1 calc R . . H10B H 0.1989 0.0517 0.0032 0.054 Uiso 1 1 calc R . . H10C H 0.0592 0.1516 -0.0238 0.054 Uiso 1 1 calc R . . C11 C 0.0786(2) 0.63388(11) 0.18715(7) 0.0237(3) Uani 1 1 d . . . C12 C 0.0322(2) 0.74905(11) 0.18414(7) 0.0232(3) Uani 1 1 d . . . C13 C -0.1410(2) 0.79318(11) 0.21012(7) 0.0235(3) Uani 1 1 d . . . C14 C -0.1726(3) 0.90012(12) 0.21351(7) 0.0301(3) Uani 1 1 d . . . H14 H -0.2928 0.9277 0.2319 0.036 Uiso 1 1 calc R . . C15 C -0.0249(3) 0.96620(13) 0.18953(8) 0.0346(4) Uani 1 1 d . . . H15 H -0.0434 1.0399 0.1911 0.042 Uiso 1 1 calc R . . C16 C 0.1479(3) 0.92475(13) 0.16347(8) 0.0341(4) Uani 1 1 d . . . H16 H 0.2492 0.9702 0.1473 0.041 Uiso 1 1 calc R . . C17 C 0.1765(2) 0.81717(12) 0.16050(7) 0.0285(3) Uani 1 1 d . . . H17 H 0.2967 0.7899 0.1420 0.034 Uiso 1 1 calc R . . N1 N -0.3073(2) 0.72513(10) 0.23136(6) 0.0270(3) Uani 1 1 d . . . O1 O 0.15043(16) 0.60199(8) 0.13214(5) 0.0250(2) Uani 1 1 d . . . O2 O 0.06059(19) 0.57958(8) 0.23421(5) 0.0339(3) Uani 1 1 d . . . O3 O -0.37136(19) 0.65077(9) 0.19614(6) 0.0377(3) Uani 1 1 d . . . O4 O -0.3784(2) 0.74853(10) 0.28202(6) 0.0431(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0241(8) 0.0205(7) 0.0241(7) -0.0001(6) 0.0064(6) 0.0015(6) C2 0.0265(8) 0.0231(7) 0.0293(8) -0.0034(6) 0.0100(6) -0.0057(6) C3 0.0223(8) 0.0255(8) 0.0268(7) -0.0047(6) 0.0100(6) -0.0048(6) C4 0.0240(8) 0.0231(7) 0.0218(7) -0.0017(6) 0.0050(6) -0.0035(6) C5 0.0251(8) 0.0248(8) 0.0356(8) -0.0022(6) 0.0120(7) -0.0069(6) C6 0.0228(8) 0.0284(8) 0.0345(8) -0.0008(6) 0.0098(6) -0.0008(6) C7 0.0274(8) 0.0226(7) 0.0266(7) -0.0035(6) 0.0072(6) -0.0052(6) C8 0.0470(10) 0.0302(8) 0.0322(8) -0.0065(7) 0.0162(7) -0.0014(7) C9 0.0340(9) 0.0241(8) 0.0347(9) 0.0006(6) 0.0066(7) -0.0012(6) C10 0.0371(9) 0.0284(8) 0.0415(9) -0.0099(7) 0.0046(7) -0.0078(7) C11 0.0223(8) 0.0252(7) 0.0244(7) -0.0001(6) 0.0057(6) 0.0017(6) C12 0.0253(8) 0.0241(7) 0.0201(7) -0.0006(6) 0.0024(6) 0.0014(6) C13 0.0261(8) 0.0236(7) 0.0204(7) -0.0006(6) 0.0017(6) 0.0000(6) C14 0.0370(9) 0.0275(8) 0.0253(7) -0.0041(6) 0.0023(6) 0.0063(7) C15 0.0507(11) 0.0204(8) 0.0316(8) -0.0023(6) 0.0019(8) 0.0007(7) C16 0.0427(10) 0.0274(8) 0.0317(8) 0.0022(7) 0.0032(7) -0.0092(7) C17 0.0288(8) 0.0296(8) 0.0275(8) 0.0019(6) 0.0050(6) -0.0015(6) N1 0.0258(7) 0.0296(7) 0.0264(6) -0.0004(5) 0.0065(5) 0.0042(5) O1 0.0294(6) 0.0218(5) 0.0252(5) 0.0005(4) 0.0088(4) 0.0028(4) O2 0.0471(7) 0.0282(6) 0.0295(6) 0.0063(5) 0.0166(5) 0.0092(5) O3 0.0389(7) 0.0369(7) 0.0383(7) -0.0081(5) 0.0091(5) -0.0121(5) O4 0.0502(8) 0.0447(7) 0.0398(7) -0.0045(6) 0.0262(6) 0.0023(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.4705(17) . ? C1 C2 1.5034(19) . ? C1 C6 1.516(2) . ? C1 H1 1.0000 . ? C2 C3 1.530(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5370(19) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5224(19) . ? C4 C7 1.555(2) . ? C4 H4 1.0000 . ? C5 C6 1.534(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.527(2) . ? C7 C10 1.542(2) . ? C7 C9 1.545(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 O2 1.2032(17) . ? C11 O1 1.3292(16) . ? C11 C12 1.499(2) . ? C12 C17 1.384(2) . ? C12 C13 1.386(2) . ? C13 C14 1.383(2) . ? C13 N1 1.4629(19) . ? C14 C15 1.387(2) . ? C14 H14 0.9500 . ? C15 C16 1.371(2) . ? C15 H15 0.9500 . ? C16 C17 1.388(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? N1 O4 1.2173(15) . ? N1 O3 1.2259(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 106.34(11) . . ? O1 C1 C6 109.63(11) . . ? C2 C1 C6 110.91(12) . . ? O1 C1 H1 110.0 . . ? C2 C1 H1 110.0 . . ? C6 C1 H1 110.0 . . ? C1 C2 C3 109.65(12) . . ? C1 C2 H2A 109.7 . . ? C3 C2 H2A 109.7 . . ? C1 C2 H2B 109.7 . . ? C3 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C2 C3 C4 111.64(12) . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C3 107.78(11) . . ? C5 C4 C7 114.55(12) . . ? C3 C4 C7 113.24(12) . . ? C5 C4 H4 106.9 . . ? C3 C4 H4 106.9 . . ? C7 C4 H4 106.9 . . ? C4 C5 C6 111.49(12) . . ? C4 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? C4 C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? C1 C6 C5 111.02(12) . . ? C1 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? C1 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C8 C7 C10 107.12(13) . . ? C8 C7 C9 108.93(13) . . ? C10 C7 C9 109.33(13) . . ? C8 C7 C4 109.10(12) . . ? C10 C7 C4 110.06(12) . . ? C9 C7 C4 112.17(12) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O2 C11 O1 125.30(13) . . ? O2 C11 C12 124.09(13) . . ? O1 C11 C12 110.55(12) . . ? C17 C12 C13 117.05(14) . . ? C17 C12 C11 120.03(13) . . ? C13 C12 C11 122.63(13) . . ? C14 C13 C12 122.98(14) . . ? C14 C13 N1 117.41(13) . . ? C12 C13 N1 119.49(13) . . ? C13 C14 C15 118.52(15) . . ? C13 C14 H14 120.7 . . ? C15 C14 H14 120.7 . . ? C16 C15 C14 119.77(15) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 120.76(15) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C12 C17 C16 120.91(15) . . ? C12 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? O4 N1 O3 124.23(13) . . ? O4 N1 C13 117.41(13) . . ? O3 N1 C13 118.31(12) . . ? C11 O1 C1 117.07(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -176.33(11) . . . . ? C6 C1 C2 C3 -57.19(16) . . . . ? C1 C2 C3 C4 59.56(16) . . . . ? C2 C3 C4 C5 -58.74(16) . . . . ? C2 C3 C4 C7 173.48(11) . . . . ? C3 C4 C5 C6 56.92(16) . . . . ? C7 C4 C5 C6 -176.06(12) . . . . ? O1 C1 C6 C5 173.44(11) . . . . ? C2 C1 C6 C5 56.30(16) . . . . ? C4 C5 C6 C1 -56.91(17) . . . . ? C5 C4 C7 C8 168.87(13) . . . . ? C3 C4 C7 C8 -66.97(16) . . . . ? C5 C4 C7 C10 51.61(17) . . . . ? C3 C4 C7 C10 175.77(12) . . . . ? C5 C4 C7 C9 -70.35(16) . . . . ? C3 C4 C7 C9 53.81(16) . . . . ? O2 C11 C12 C17 133.72(16) . . . . ? O1 C11 C12 C17 -43.58(18) . . . . ? O2 C11 C12 C13 -39.9(2) . . . . ? O1 C11 C12 C13 142.81(14) . . . . ? C17 C12 C13 C14 -0.5(2) . . . . ? C11 C12 C13 C14 173.32(14) . . . . ? C17 C12 C13 N1 175.51(13) . . . . ? C11 C12 C13 N1 -10.7(2) . . . . ? C12 C13 C14 C15 0.3(2) . . . . ? N1 C13 C14 C15 -175.71(13) . . . . ? C13 C14 C15 C16 -0.2(2) . . . . ? C14 C15 C16 C17 0.3(2) . . . . ? C13 C12 C17 C16 0.5(2) . . . . ? C11 C12 C17 C16 -173.45(14) . . . . ? C15 C16 C17 C12 -0.4(2) . . . . ? C14 C13 N1 O4 -43.92(19) . . . . ? C12 C13 N1 O4 139.88(14) . . . . ? C14 C13 N1 O3 133.59(15) . . . . ? C12 C13 N1 O3 -42.60(19) . . . . ? O2 C11 O1 C1 -4.3(2) . . . . ? C12 C11 O1 C1 172.99(11) . . . . ? C2 C1 O1 C11 -154.35(12) . . . . ? C6 C1 O1 C11 85.68(14) . . . . ? _diffrn_measured_fraction_theta_max 0.909 _diffrn_reflns_theta_full 28.49 _diffrn_measured_fraction_theta_full 0.909 _refine_diff_density_max 0.251 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.040 data_compound5f _database_code_CSD 205445 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H24 O3 S' _chemical_formula_weight 296.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 24.7358(3) _cell_length_b 6.20220(10) _cell_length_c 20.9387(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.4870(10) _cell_angle_gamma 90.00 _cell_volume 3158.68(9) _cell_formula_units_Z 8 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 40594 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.210 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130.0(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _diffrn_measurement_method CCD _diffrn_standards_decay_% ? _diffrn_reflns_number 38021 _diffrn_reflns_av_R_equivalents 0.0579 _diffrn_reflns_av_sigmaI/netI 0.0610 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 28.28 _reflns_number_total 7783 _reflns_number_gt 5301 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+0.5290P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7783 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0816 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1112 _refine_ls_wR_factor_gt 0.0989 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S S 0.361173(18) 0.29280(7) 0.24489(2) 0.02563(12) Uani 1 1 d . . . O1 O 0.30604(5) 0.16307(17) 0.22969(5) 0.0245(3) Uani 1 1 d . . . O3 O 0.37704(5) 0.2829(2) 0.31369(6) 0.0354(3) Uani 1 1 d . . . O2 O 0.35482(5) 0.49650(18) 0.21297(7) 0.0362(3) Uani 1 1 d . . . C4 C 0.17243(7) 0.0448(2) 0.07297(8) 0.0211(4) Uani 1 1 d . . . H4 H 0.1535 -0.0163 0.1072 0.025 Uiso 1 1 calc R . . C1 C 0.27472(7) 0.1620(3) 0.16190(8) 0.0227(4) Uani 1 1 d . . . H1 H 0.2978 0.2260 0.1321 0.027 Uiso 1 1 calc R . . C2 C 0.26208(7) -0.0698(3) 0.14364(8) 0.0265(4) Uani 1 1 d . . . H2A H 0.2428 -0.1379 0.1760 0.032 Uiso 1 1 calc R . . H2B H 0.2968 -0.1495 0.1436 0.032 Uiso 1 1 calc R . . C3 C 0.22601(7) -0.0819(3) 0.07644(8) 0.0282(4) Uani 1 1 d . . . H3A H 0.2172 -0.2347 0.0654 0.034 Uiso 1 1 calc R . . H3B H 0.2466 -0.0236 0.0439 0.034 Uiso 1 1 calc R . . C5 C 0.18706(7) 0.2788(3) 0.09249(8) 0.0263(4) Uani 1 1 d . . . H5A H 0.2064 0.3448 0.0600 0.032 Uiso 1 1 calc R . . H5B H 0.1528 0.3613 0.0925 0.032 Uiso 1 1 calc R . . C6 C 0.22347(7) 0.2944(3) 0.15960(8) 0.0265(4) Uani 1 1 d . . . H6A H 0.2336 0.4469 0.1694 0.032 Uiso 1 1 calc R . . H6B H 0.2029 0.2419 0.1929 0.032 Uiso 1 1 calc R . . C7 C 0.13178(7) 0.0212(3) 0.00724(8) 0.0228(4) Uani 1 1 d . . . C8 C 0.15360(7) 0.1279(3) -0.04910(8) 0.0282(4) Uani 1 1 d . . . H8A H 0.1605 0.2812 -0.0395 0.042 Uiso 1 1 calc R . . H8B H 0.1263 0.1130 -0.0891 0.042 Uiso 1 1 calc R . . H8C H 0.1879 0.0577 -0.0547 0.042 Uiso 1 1 calc R . . C9 C 0.12121(8) -0.2182(3) -0.00837(9) 0.0382(5) Uani 1 1 d . . . H9A H 0.1073 -0.2878 0.0274 0.057 Uiso 1 1 calc R . . H9B H 0.1556 -0.2876 -0.0141 0.057 Uiso 1 1 calc R . . H9C H 0.0939 -0.2323 -0.0484 0.057 Uiso 1 1 calc R . . C10 C 0.07645(7) 0.1254(3) 0.01263(9) 0.0338(4) Uani 1 1 d . . . H10A H 0.0820 0.2790 0.0227 0.051 Uiso 1 1 calc R . . H10B H 0.0612 0.0546 0.0473 0.051 Uiso 1 1 calc R . . H10C H 0.0508 0.1091 -0.0287 0.051 Uiso 1 1 calc R . . C11 C 0.40718(7) 0.1358(3) 0.20937(8) 0.0228(4) Uani 1 1 d . . . C12 C 0.42261(7) -0.0655(3) 0.23575(9) 0.0283(4) Uani 1 1 d . . . H12 H 0.4076 -0.1192 0.2713 0.034 Uiso 1 1 calc R . . C13 C 0.46020(7) -0.1864(3) 0.20942(9) 0.0327(4) Uani 1 1 d . . . H13 H 0.4710 -0.3245 0.2268 0.039 Uiso 1 1 calc R . . C14 C 0.48201(7) -0.1072(3) 0.15797(9) 0.0359(5) Uani 1 1 d . . . H14 H 0.5084 -0.1896 0.1408 0.043 Uiso 1 1 calc R . . C15 C 0.46567(8) 0.0913(3) 0.13135(9) 0.0381(5) Uani 1 1 d . . . H15 H 0.4802 0.1433 0.0953 0.046 Uiso 1 1 calc R . . C16 C 0.42804(7) 0.2151(3) 0.15702(9) 0.0301(4) Uani 1 1 d . . . H16 H 0.4168 0.3520 0.1390 0.036 Uiso 1 1 calc R . . S' S 0.124074(17) 0.67607(7) 0.24608(2) 0.02367(12) Uani 1 1 d . . . O1' O 0.17484(4) 0.82687(17) 0.26743(5) 0.0234(3) Uani 1 1 d . . . O2' O 0.10471(5) 0.73003(19) 0.17944(6) 0.0324(3) Uani 1 1 d . . . O3' O 0.13776(5) 0.45715(17) 0.26313(6) 0.0307(3) Uani 1 1 d . . . C1' C 0.21068(7) 0.7990(2) 0.33241(8) 0.0222(4) Uani 1 1 d . . . H1' H 0.1887 0.7388 0.3639 0.027 Uiso 1 1 calc R . . C2' C 0.23034(7) 1.0231(3) 0.35318(8) 0.0245(4) Uani 1 1 d . . . H2'1 H 0.1986 1.1124 0.3596 0.029 Uiso 1 1 calc R . . H2'2 H 0.2470 1.0905 0.3185 0.029 Uiso 1 1 calc R . . C3' C 0.27270(7) 1.0165(3) 0.41621(8) 0.0269(4) Uani 1 1 d . . . H3'1 H 0.2551 0.9614 0.4518 0.032 Uiso 1 1 calc R . . H3'2 H 0.2860 1.1645 0.4278 0.032 Uiso 1 1 calc R . . C4' C 0.32167(7) 0.8716(2) 0.40931(8) 0.0230(4) Uani 1 1 d . . . H4' H 0.3366 0.9280 0.3713 0.028 Uiso 1 1 calc R . . C5' C 0.29933(7) 0.6455(3) 0.39045(8) 0.0262(4) Uani 1 1 d . . . H5'1 H 0.3302 0.5489 0.3857 0.031 Uiso 1 1 calc R . . H5'2 H 0.2816 0.5872 0.4255 0.031 Uiso 1 1 calc R . . C6' C 0.25765(7) 0.6492(3) 0.32683(9) 0.0265(4) Uani 1 1 d . . . H6'1 H 0.2759 0.6978 0.2911 0.032 Uiso 1 1 calc R . . H6'2 H 0.2433 0.5018 0.3165 0.032 Uiso 1 1 calc R . . C7' C 0.36987(7) 0.8781(3) 0.46824(9) 0.0289(4) Uani 1 1 d . . . C8' C 0.38956(8) 1.1118(3) 0.48088(10) 0.0399(5) Uani 1 1 d . . . H8'1 H 0.4003 1.1707 0.4416 0.060 Uiso 1 1 calc R . . H8'2 H 0.4212 1.1148 0.5167 0.060 Uiso 1 1 calc R . . H8'3 H 0.3597 1.1989 0.4924 0.060 Uiso 1 1 calc R . . C9' C 0.35361(8) 0.7883(3) 0.53039(9) 0.0379(5) Uani 1 1 d . . . H9'1 H 0.3409 0.6391 0.5230 0.057 Uiso 1 1 calc R . . H9'2 H 0.3240 0.8762 0.5421 0.057 Uiso 1 1 calc R . . H9'3 H 0.3855 0.7921 0.5658 0.057 Uiso 1 1 calc R . . C10' C 0.41812(8) 0.7476(3) 0.45206(10) 0.0424(5) Uani 1 1 d . . . H10D H 0.4068 0.5972 0.4439 0.064 Uiso 1 1 calc R . . H10E H 0.4490 0.7543 0.4887 0.064 Uiso 1 1 calc R . . H10F H 0.4294 0.8079 0.4132 0.064 Uiso 1 1 calc R . . C11' C 0.07577(7) 0.7620(2) 0.29323(8) 0.0209(4) Uani 1 1 d . . . C12' C 0.03632(7) 0.6127(3) 0.30380(8) 0.0238(4) Uani 1 1 d . . . H12' H 0.0374 0.4693 0.2881 0.029 Uiso 1 1 calc R . . C13' C -0.00439(7) 0.6750(3) 0.33730(8) 0.0271(4) Uani 1 1 d . . . H13' H -0.0319 0.5750 0.3439 0.033 Uiso 1 1 calc R . . C14' C -0.00496(7) 0.8838(3) 0.36125(8) 0.0273(4) Uani 1 1 d . . . H14' H -0.0326 0.9258 0.3848 0.033 Uiso 1 1 calc R . . C15' C 0.03475(7) 1.0310(3) 0.35084(8) 0.0265(4) Uani 1 1 d . . . H15' H 0.0343 1.1730 0.3677 0.032 Uiso 1 1 calc R . . C16' C 0.07501(7) 0.9723(3) 0.31602(8) 0.0245(4) Uani 1 1 d . . . H16' H 0.1016 1.0741 0.3078 0.029 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S 0.0218(2) 0.0259(2) 0.0288(3) -0.00404(18) 0.00338(18) -0.00272(17) O1 0.0194(6) 0.0317(7) 0.0216(6) 0.0002(5) 0.0020(5) -0.0043(5) O3 0.0298(7) 0.0494(8) 0.0258(7) -0.0121(6) 0.0023(6) -0.0039(6) O2 0.0334(7) 0.0204(6) 0.0542(9) 0.0000(6) 0.0064(6) -0.0020(5) C4 0.0237(9) 0.0198(8) 0.0204(9) 0.0012(6) 0.0052(7) -0.0013(7) C1 0.0217(9) 0.0283(9) 0.0175(8) 0.0011(7) 0.0021(7) -0.0021(7) C2 0.0272(10) 0.0236(9) 0.0269(10) -0.0016(7) 0.0004(8) 0.0052(7) C3 0.0331(10) 0.0237(9) 0.0265(10) -0.0040(7) 0.0017(8) 0.0051(8) C5 0.0262(9) 0.0228(9) 0.0282(10) -0.0021(7) 0.0000(8) 0.0031(7) C6 0.0274(10) 0.0218(9) 0.0282(10) -0.0049(7) -0.0006(8) 0.0014(7) C7 0.0236(9) 0.0224(9) 0.0223(9) -0.0002(7) 0.0036(7) -0.0014(7) C8 0.0300(10) 0.0308(10) 0.0237(9) 0.0006(7) 0.0046(8) 0.0014(8) C9 0.0451(12) 0.0280(10) 0.0351(11) -0.0003(8) -0.0095(9) -0.0100(9) C10 0.0237(10) 0.0489(12) 0.0283(10) -0.0005(8) 0.0035(8) -0.0015(8) C11 0.0175(8) 0.0243(9) 0.0254(9) -0.0016(7) 0.0008(7) -0.0023(7) C12 0.0261(10) 0.0263(10) 0.0311(10) 0.0001(7) 0.0018(8) -0.0047(7) C13 0.0252(10) 0.0274(10) 0.0425(12) -0.0026(8) -0.0019(9) 0.0007(8) C14 0.0208(10) 0.0467(12) 0.0384(12) -0.0122(9) 0.0001(8) 0.0046(8) C15 0.0275(10) 0.0578(13) 0.0300(11) 0.0040(9) 0.0076(9) 0.0018(9) C16 0.0253(10) 0.0351(10) 0.0294(10) 0.0050(8) 0.0036(8) 0.0010(8) S' 0.0226(2) 0.0258(2) 0.0232(2) -0.00168(17) 0.00573(18) -0.00365(17) O1' 0.0201(6) 0.0263(6) 0.0233(6) 0.0019(5) 0.0030(5) -0.0038(5) O2' 0.0318(7) 0.0451(8) 0.0202(7) -0.0014(5) 0.0043(5) -0.0095(6) O3' 0.0313(7) 0.0210(6) 0.0419(8) -0.0029(5) 0.0122(6) -0.0005(5) C1' 0.0222(9) 0.0252(9) 0.0189(9) 0.0015(7) 0.0028(7) -0.0022(7) C2' 0.0236(9) 0.0217(9) 0.0288(10) -0.0010(7) 0.0063(7) 0.0018(7) C3' 0.0274(10) 0.0229(9) 0.0296(10) -0.0051(7) 0.0032(8) -0.0006(7) C4' 0.0235(9) 0.0219(9) 0.0244(9) -0.0008(7) 0.0061(7) -0.0012(7) C5' 0.0252(9) 0.0234(9) 0.0292(10) -0.0004(7) 0.0028(8) 0.0042(7) C6' 0.0273(9) 0.0219(9) 0.0300(10) -0.0040(7) 0.0045(8) 0.0003(7) C7' 0.0241(9) 0.0327(10) 0.0290(10) -0.0006(8) 0.0028(8) -0.0006(8) C8' 0.0385(12) 0.0404(11) 0.0355(11) -0.0018(9) -0.0072(9) -0.0113(9) C9' 0.0328(11) 0.0489(12) 0.0295(11) 0.0057(9) -0.0010(9) -0.0017(9) C10' 0.0254(11) 0.0558(13) 0.0445(13) -0.0069(10) 0.0021(9) 0.0037(9) C11' 0.0205(9) 0.0228(9) 0.0185(9) 0.0031(7) 0.0013(7) 0.0017(7) C12' 0.0264(9) 0.0233(9) 0.0211(9) 0.0011(7) 0.0026(7) -0.0026(7) C13' 0.0238(9) 0.0330(10) 0.0247(9) 0.0040(7) 0.0046(7) -0.0039(8) C14' 0.0241(9) 0.0359(10) 0.0224(9) 0.0050(7) 0.0052(7) 0.0070(8) C15' 0.0295(10) 0.0234(9) 0.0257(9) 0.0022(7) 0.0029(8) 0.0038(7) C16' 0.0229(9) 0.0246(9) 0.0251(9) 0.0037(7) 0.0017(7) -0.0004(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S O3 1.4238(13) . ? S O2 1.4246(12) . ? S O1 1.5655(11) . ? S C11 1.7620(17) . ? O1 C1 1.4882(18) . ? C4 C3 1.531(2) . ? C4 C5 1.533(2) . ? C4 C7 1.557(2) . ? C4 H4 1.0000 . ? C1 C6 1.504(2) . ? C1 C2 1.506(2) . ? C1 H1 1.0000 . ? C2 C3 1.525(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C5 C6 1.528(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C9 1.533(2) . ? C7 C8 1.534(2) . ? C7 C10 1.536(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C16 1.384(2) . ? C11 C12 1.390(2) . ? C12 C13 1.385(2) . ? C12 H12 0.9500 . ? C13 C14 1.380(3) . ? C13 H13 0.9500 . ? C14 C15 1.381(3) . ? C14 H14 0.9500 . ? C15 C16 1.388(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? S' O3' 1.4288(12) . ? S' O2' 1.4300(12) . ? S' O1' 1.5644(11) . ? S' C11' 1.7652(17) . ? O1' C1' 1.4926(18) . ? C1' C6' 1.509(2) . ? C1' C2' 1.510(2) . ? C1' H1' 1.0000 . ? C2' C3' 1.529(2) . ? C2' H2'1 0.9900 . ? C2' H2'2 0.9900 . ? C3' C4' 1.536(2) . ? C3' H3'1 0.9900 . ? C3' H3'2 0.9900 . ? C4' C5' 1.533(2) . ? C4' C7' 1.552(2) . ? C4' H4' 1.0000 . ? C5' C6' 1.529(2) . ? C5' H5'1 0.9900 . ? C5' H5'2 0.9900 . ? C6' H6'1 0.9900 . ? C6' H6'2 0.9900 . ? C7' C10' 1.530(2) . ? C7' C9' 1.535(2) . ? C7' C8' 1.537(2) . ? C8' H8'1 0.9800 . ? C8' H8'2 0.9800 . ? C8' H8'3 0.9800 . ? C9' H9'1 0.9800 . ? C9' H9'2 0.9800 . ? C9' H9'3 0.9800 . ? C10' H10D 0.9800 . ? C10' H10E 0.9800 . ? C10' H10F 0.9800 . ? C11' C16' 1.390(2) . ? C11' C12' 1.392(2) . ? C12' C13' 1.383(2) . ? C12' H12' 0.9500 . ? C13' C14' 1.390(2) . ? C13' H13' 0.9500 . ? C14' C15' 1.387(2) . ? C14' H14' 0.9500 . ? C15' C16' 1.386(2) . ? C15' H15' 0.9500 . ? C16' H16' 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S O2 119.97(8) . . ? O3 S O1 104.66(7) . . ? O2 S O1 110.04(7) . . ? O3 S C11 108.84(8) . . ? O2 S C11 108.46(8) . . ? O1 S C11 103.64(7) . . ? C1 O1 S 118.63(10) . . ? C3 C4 C5 108.23(13) . . ? C3 C4 C7 114.06(13) . . ? C5 C4 C7 114.09(13) . . ? C3 C4 H4 106.6 . . ? C5 C4 H4 106.6 . . ? C7 C4 H4 106.6 . . ? O1 C1 C6 108.51(13) . . ? O1 C1 C2 107.12(12) . . ? C6 C1 C2 112.24(14) . . ? O1 C1 H1 109.6 . . ? C6 C1 H1 109.6 . . ? C2 C1 H1 109.6 . . ? C1 C2 C3 109.92(13) . . ? C1 C2 H2A 109.7 . . ? C3 C2 H2A 109.7 . . ? C1 C2 H2B 109.7 . . ? C3 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C2 C3 C4 112.00(14) . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C6 C5 C4 112.12(13) . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5B 109.2 . . ? C4 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C1 C6 C5 110.30(14) . . ? C1 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? C1 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C9 C7 C8 108.91(14) . . ? C9 C7 C10 107.67(15) . . ? C8 C7 C10 108.53(14) . . ? C9 C7 C4 109.73(13) . . ? C8 C7 C4 112.24(13) . . ? C10 C7 C4 109.65(13) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 121.26(16) . . ? C16 C11 S 120.03(13) . . ? C12 C11 S 118.70(13) . . ? C13 C12 C11 118.94(17) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C14 C13 C12 120.27(17) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 120.35(18) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C15 C16 120.28(18) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C11 C16 C15 118.87(17) . . ? C11 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? O3' S' O2' 119.22(7) . . ? O3' S' O1' 110.82(7) . . ? O2' S' O1' 104.34(7) . . ? O3' S' C11' 107.50(7) . . ? O2' S' C11' 109.55(7) . . ? O1' S' C11' 104.45(7) . . ? C1' O1' S' 120.27(9) . . ? O1' C1' C6' 109.79(13) . . ? O1' C1' C2' 105.24(12) . . ? C6' C1' C2' 112.15(14) . . ? O1' C1' H1' 109.9 . . ? C6' C1' H1' 109.9 . . ? C2' C1' H1' 109.9 . . ? C1' C2' C3' 111.00(13) . . ? C1' C2' H2'1 109.4 . . ? C3' C2' H2'1 109.4 . . ? C1' C2' H2'2 109.4 . . ? C3' C2' H2'2 109.4 . . ? H2'1 C2' H2'2 108.0 . . ? C2' C3' C4' 111.25(14) . . ? C2' C3' H3'1 109.4 . . ? C4' C3' H3'1 109.4 . . ? C2' C3' H3'2 109.4 . . ? C4' C3' H3'2 109.4 . . ? H3'1 C3' H3'2 108.0 . . ? C5' C4' C3' 107.82(13) . . ? C5' C4' C7' 114.65(13) . . ? C3' C4' C7' 114.51(13) . . ? C5' C4' H4' 106.4 . . ? C3' C4' H4' 106.4 . . ? C7' C4' H4' 106.4 . . ? C6' C5' C4' 111.43(13) . . ? C6' C5' H5'1 109.3 . . ? C4' C5' H5'1 109.3 . . ? C6' C5' H5'2 109.3 . . ? C4' C5' H5'2 109.3 . . ? H5'1 C5' H5'2 108.0 . . ? C1' C6' C5' 110.39(13) . . ? C1' C6' H6'1 109.6 . . ? C5' C6' H6'1 109.6 . . ? C1' C6' H6'2 109.6 . . ? C5' C6' H6'2 109.6 . . ? H6'1 C6' H6'2 108.1 . . ? C10' C7' C9' 109.35(16) . . ? C10' C7' C8' 107.54(16) . . ? C9' C7' C8' 108.67(15) . . ? C10' C7' C4' 109.12(14) . . ? C9' C7' C4' 112.50(15) . . ? C8' C7' C4' 109.55(14) . . ? C7' C8' H8'1 109.5 . . ? C7' C8' H8'2 109.5 . . ? H8'1 C8' H8'2 109.5 . . ? C7' C8' H8'3 109.5 . . ? H8'1 C8' H8'3 109.5 . . ? H8'2 C8' H8'3 109.5 . . ? C7' C9' H9'1 109.5 . . ? C7' C9' H9'2 109.5 . . ? H9'1 C9' H9'2 109.5 . . ? C7' C9' H9'3 109.5 . . ? H9'1 C9' H9'3 109.5 . . ? H9'2 C9' H9'3 109.5 . . ? C7' C10' H10D 109.5 . . ? C7' C10' H10E 109.5 . . ? H10D C10' H10E 109.5 . . ? C7' C10' H10F 109.5 . . ? H10D C10' H10F 109.5 . . ? H10E C10' H10F 109.5 . . ? C16' C11' C12' 121.07(16) . . ? C16' C11' S' 121.86(13) . . ? C12' C11' S' 116.98(12) . . ? C13' C12' C11' 119.41(15) . . ? C13' C12' H12' 120.3 . . ? C11' C12' H12' 120.3 . . ? C12' C13' C14' 119.97(16) . . ? C12' C13' H13' 120.0 . . ? C14' C13' H13' 120.0 . . ? C15' C14' C13' 120.17(16) . . ? C15' C14' H14' 119.9 . . ? C13' C14' H14' 119.9 . . ? C16' C15' C14' 120.49(16) . . ? C16' C15' H15' 119.8 . . ? C14' C15' H15' 119.8 . . ? C15' C16' C11' 118.86(16) . . ? C15' C16' H16' 120.6 . . ? C11' C16' H16' 120.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 S O1 C1 173.31(11) . . . . ? O2 S O1 C1 43.14(12) . . . . ? C11 S O1 C1 -72.67(12) . . . . ? S O1 C1 C6 -109.05(13) . . . . ? S O1 C1 C2 129.56(12) . . . . ? O1 C1 C2 C3 175.53(13) . . . . ? C6 C1 C2 C3 56.53(19) . . . . ? C1 C2 C3 C4 -57.54(19) . . . . ? C5 C4 C3 C2 56.98(18) . . . . ? C7 C4 C3 C2 -174.87(13) . . . . ? C3 C4 C5 C6 -56.24(18) . . . . ? C7 C4 C5 C6 175.63(14) . . . . ? O1 C1 C6 C5 -174.14(13) . . . . ? C2 C1 C6 C5 -55.95(19) . . . . ? C4 C5 C6 C1 56.28(19) . . . . ? C3 C4 C7 C9 53.42(19) . . . . ? C5 C4 C7 C9 178.52(15) . . . . ? C3 C4 C7 C8 -67.82(17) . . . . ? C5 C4 C7 C8 57.28(18) . . . . ? C3 C4 C7 C10 171.48(14) . . . . ? C5 C4 C7 C10 -63.42(18) . . . . ? O3 S C11 C16 -135.17(14) . . . . ? O2 S C11 C16 -3.08(16) . . . . ? O1 S C11 C16 113.85(14) . . . . ? O3 S C11 C12 43.61(15) . . . . ? O2 S C11 C12 175.71(13) . . . . ? O1 S C11 C12 -67.37(14) . . . . ? C16 C11 C12 C13 0.9(2) . . . . ? S C11 C12 C13 -177.82(13) . . . . ? C11 C12 C13 C14 0.2(3) . . . . ? C12 C13 C14 C15 -1.4(3) . . . . ? C13 C14 C15 C16 1.4(3) . . . . ? C12 C11 C16 C15 -0.9(3) . . . . ? S C11 C16 C15 177.81(13) . . . . ? C14 C15 C16 C11 -0.2(3) . . . . ? O3' S' O1' C1' -42.92(13) . . . . ? O2' S' O1' C1' -172.44(11) . . . . ? C11' S' O1' C1' 72.57(12) . . . . ? S' O1' C1' C6' 91.99(14) . . . . ? S' O1' C1' C2' -147.12(11) . . . . ? O1' C1' C2' C3' -173.92(13) . . . . ? C6' C1' C2' C3' -54.60(19) . . . . ? C1' C2' C3' C4' 56.73(19) . . . . ? C2' C3' C4' C5' -58.21(18) . . . . ? C2' C3' C4' C7' 172.88(14) . . . . ? C3' C4' C5' C6' 58.97(18) . . . . ? C7' C4' C5' C6' -172.20(14) . . . . ? O1' C1' C6' C5' 171.51(12) . . . . ? C2' C1' C6' C5' 54.88(19) . . . . ? C4' C5' C6' C1' -57.85(19) . . . . ? C5' C4' C7' C10' 60.8(2) . . . . ? C3' C4' C7' C10' -173.75(15) . . . . ? C5' C4' C7' C9' -60.7(2) . . . . ? C3' C4' C7' C9' 64.71(19) . . . . ? C5' C4' C7' C8' 178.33(15) . . . . ? C3' C4' C7' C8' -56.3(2) . . . . ? O3' S' C11' C16' 145.13(13) . . . . ? O2' S' C11' C16' -83.94(14) . . . . ? O1' S' C11' C16' 27.34(15) . . . . ? O3' S' C11' C12' -38.26(14) . . . . ? O2' S' C11' C12' 92.67(13) . . . . ? O1' S' C11' C12' -156.05(12) . . . . ? C16' C11' C12' C13' 0.2(2) . . . . ? S' C11' C12' C13' -176.40(12) . . . . ? C11' C12' C13' C14' -1.3(2) . . . . ? C12' C13' C14' C15' 0.9(2) . . . . ? C13' C14' C15' C16' 0.6(2) . . . . ? C14' C15' C16' C11' -1.7(2) . . . . ? C12' C11' C16' C15' 1.3(2) . . . . ? S' C11' C16' C15' 177.75(12) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.268 _refine_diff_density_min -0.414 _refine_diff_density_rms 0.052 data_compound5g _database_code_CSD 205446 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 75.5-77 _chemical_formula_moiety ? _chemical_formula_sum 'C17 H26 O3 S' _chemical_formula_weight 310.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.2680(14) _cell_length_b 10.4090(15) _cell_length_c 13.1900(19) _cell_angle_alpha 94.300(11) _cell_angle_beta 95.040(15) _cell_angle_gamma 98.830(15) _cell_volume 843.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 130.0(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 20 _cell_measurement_theta_max 30 _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.050 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 1.761 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.66 _exptl_absorpt_correction_T_max 0.91 _exptl_absorpt_process_details 'ABSORB Platon' _exptl_special_details ; ? ; _diffrn_ambient_temperature 130.0(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method \q2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 9600 _diffrn_standards_decay_% 2 _diffrn_reflns_number 3519 _diffrn_reflns_av_R_equivalents 0.0158 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 69.93 _reflns_number_total 3204 _reflns_number_gt 2819 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software 5.0 (Enraf-Nonius, 1989)' _computing_cell_refinement ? _computing_data_reduction 'PROCESS_DATA (Gable et al., 1994)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0556P)^2^+0.3223P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0104(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3204 _refine_ls_number_parameters 295 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0442 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.1009 _refine_ls_wR_factor_gt 0.0954 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2670(3) 0.33404(14) 0.56967(12) 0.0228(3) Uani 1 1 d . . . C2 C 0.4826(3) 0.30312(15) 0.54065(12) 0.0249(3) Uani 1 1 d . . . C3 C 0.4500(3) 0.17734(16) 0.46908(12) 0.0250(3) Uani 1 1 d . . . C4 C 0.2958(2) 0.18461(14) 0.37350(11) 0.0208(3) Uani 1 1 d . . . C5 C 0.0791(2) 0.21286(16) 0.40774(13) 0.0252(3) Uani 1 1 d . . . C6 C 0.1081(3) 0.33977(16) 0.47780(13) 0.0267(3) Uani 1 1 d . . . C7 C 0.2718(3) 0.06458(15) 0.29328(12) 0.0253(3) Uani 1 1 d . . . C8 C 0.4970(3) 0.03684(19) 0.26953(15) 0.0344(4) Uani 1 1 d . . . C9 C 0.1465(3) -0.05806(17) 0.33027(15) 0.0332(4) Uani 1 1 d . . . C10 C 0.1519(3) 0.0955(2) 0.19375(14) 0.0382(4) Uani 1 1 d . . . C11 C 0.3547(3) 0.40894(16) 0.81732(12) 0.0278(3) Uani 1 1 d . . . C12 C 0.5727(3) 0.4556(2) 0.84418(15) 0.0401(4) Uani 1 1 d . . . C13 C 0.6881(3) 0.3899(2) 0.91185(16) 0.0456(5) Uani 1 1 d . . . C14 C 0.5916(3) 0.27921(19) 0.95220(13) 0.0394(4) Uani 1 1 d . . . C15 C 0.3727(4) 0.23587(19) 0.92554(14) 0.0400(4) Uani 1 1 d . . . C16 C 0.2520(3) 0.29985(17) 0.85788(13) 0.0343(4) Uani 1 1 d . . . C17 C 0.7228(5) 0.2059(3) 1.02267(17) 0.0565(7) Uani 1 1 d . . . O1 O 0.31401(18) 0.46526(10) 0.62727(8) 0.0263(3) Uani 1 1 d . . . O2 O 0.2600(2) 0.62646(12) 0.75390(10) 0.0415(3) Uani 1 1 d . . . 03 O -0.0138(2) 0.42646(13) 0.71693(9) 0.0378(3) Uani 1 1 d . . . S1 S 0.20759(7) 0.48867(4) 0.72871(3) 0.02831(15) Uani 1 1 d . . . H1 H 0.209(3) 0.2740(18) 0.6167(14) 0.025(4) Uiso 1 1 d . . . H3A H 0.392(3) 0.1044(19) 0.5033(15) 0.030(5) Uiso 1 1 d . . . H3B H 0.593(3) 0.164(2) 0.4492(16) 0.040(5) Uiso 1 1 d . . . H4 H 0.361(3) 0.2570(17) 0.3390(13) 0.021(4) Uiso 1 1 d . . . H4A H 0.576(3) 0.2967(18) 0.6022(15) 0.029(5) Uiso 1 1 d . . . H4B H 0.555(3) 0.3755(18) 0.5063(14) 0.026(4) Uiso 1 1 d . . . H5A H -0.022(3) 0.2167(19) 0.3504(16) 0.039(5) Uiso 1 1 d . . . H5B H 0.009(3) 0.1396(19) 0.4444(14) 0.029(5) Uiso 1 1 d . . . H6A H -0.028(4) 0.354(2) 0.5027(16) 0.042(6) Uiso 1 1 d . . . H6B H 0.165(3) 0.4137(18) 0.4413(14) 0.027(5) Uiso 1 1 d . . . H8A H 0.590(4) 0.115(2) 0.2482(17) 0.048(6) Uiso 1 1 d . . . H8B H 0.576(4) -0.001(2) 0.3275(18) 0.047(6) Uiso 1 1 d . . . H8C H 0.482(3) -0.027(2) 0.2091(17) 0.043(6) Uiso 1 1 d . . . H9A H 0.209(4) -0.077(2) 0.3995(18) 0.046(6) Uiso 1 1 d . . . H9B H 0.147(4) -0.131(2) 0.2825(17) 0.046(6) Uiso 1 1 d . . . H9C H -0.007(3) -0.0517(19) 0.3344(15) 0.037(5) Uiso 1 1 d . . . H10A H 0.140(4) 0.024(2) 0.1405(18) 0.050(6) Uiso 1 1 d . . . H10B H 0.240(4) 0.171(2) 0.1672(18) 0.054(7) Uiso 1 1 d . . . H10C H -0.001(4) 0.110(2) 0.2010(18) 0.052(6) Uiso 1 1 d . . . H12 H 0.640(4) 0.529(2) 0.8144(17) 0.047(6) Uiso 1 1 d . . . H13 H 0.831(4) 0.421(2) 0.9303(19) 0.058(7) Uiso 1 1 d . . . H15 H 0.301(4) 0.159(2) 0.9552(17) 0.048(6) Uiso 1 1 d . . . H16 H 0.097(4) 0.270(2) 0.8392(16) 0.042(6) Uiso 1 1 d . . . H17A H 0.640(8) 0.143(5) 1.055(4) 0.153(19) Uiso 1 1 d . . . H17B H 0.850(7) 0.179(4) 0.988(3) 0.137(15) Uiso 1 1 d . . . H17C H 0.783(6) 0.261(4) 1.081(3) 0.122(13) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0301(8) 0.0170(7) 0.0206(7) 0.0004(6) 0.0038(6) 0.0016(6) C2 0.0248(8) 0.0258(8) 0.0235(8) 0.0009(6) -0.0023(6) 0.0049(6) C3 0.0238(8) 0.0258(8) 0.0252(8) 0.0004(6) -0.0025(6) 0.0077(6) C4 0.0220(7) 0.0194(7) 0.0211(7) 0.0032(6) 0.0013(6) 0.0031(5) C5 0.0211(7) 0.0261(8) 0.0276(8) -0.0016(6) -0.0017(6) 0.0058(6) C6 0.0240(8) 0.0256(8) 0.0310(9) -0.0010(7) 0.0002(6) 0.0082(6) C7 0.0282(8) 0.0251(8) 0.0223(8) -0.0013(6) 0.0002(6) 0.0060(6) C8 0.0339(9) 0.0362(10) 0.0332(9) -0.0074(8) 0.0058(7) 0.0096(8) C9 0.0355(10) 0.0230(8) 0.0383(10) -0.0035(7) -0.0011(7) 0.0018(7) C10 0.0476(11) 0.0443(11) 0.0223(9) -0.0025(8) -0.0041(8) 0.0132(9) C11 0.0368(9) 0.0296(8) 0.0181(7) -0.0003(6) 0.0031(6) 0.0101(7) C12 0.0355(10) 0.0477(11) 0.0384(10) 0.0115(9) 0.0050(8) 0.0062(8) C13 0.0367(11) 0.0638(14) 0.0372(11) 0.0042(9) -0.0007(8) 0.0140(10) C14 0.0588(12) 0.0472(11) 0.0172(8) -0.0011(7) 0.0034(7) 0.0269(9) C15 0.0592(12) 0.0332(10) 0.0284(9) 0.0055(7) 0.0034(8) 0.0096(9) C16 0.0431(10) 0.0306(9) 0.0276(9) 0.0003(7) 0.0015(7) 0.0031(8) C17 0.0808(17) 0.0721(16) 0.0257(10) 0.0035(10) -0.0013(10) 0.0453(14) O1 0.0349(6) 0.0207(5) 0.0227(6) -0.0002(4) 0.0055(4) 0.0023(4) O2 0.0642(9) 0.0280(7) 0.0342(7) -0.0034(5) 0.0041(6) 0.0169(6) 03 0.0320(7) 0.0526(8) 0.0318(7) 0.0065(6) 0.0067(5) 0.0132(6) S1 0.0369(2) 0.0280(2) 0.0220(2) 0.00070(15) 0.00494(15) 0.01127(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.4869(17) . ? C1 C2 1.510(2) . ? C1 C6 1.510(2) . ? C1 H1 0.968(19) . ? C2 C3 1.532(2) . ? C2 H4A 0.970(19) . ? C2 H4B 0.981(19) . ? C3 C4 1.534(2) . ? C3 H3A 0.95(2) . ? C3 H3B 0.98(2) . ? C4 C5 1.531(2) . ? C4 C7 1.555(2) . ? C4 H4 0.965(18) . ? C5 C6 1.532(2) . ? C5 H5A 0.95(2) . ? C5 H5B 1.00(2) . ? C6 H6A 0.97(2) . ? C6 H6B 0.976(19) . ? C7 C9 1.529(2) . ? C7 C10 1.535(2) . ? C7 C8 1.537(2) . ? C8 H8A 1.00(2) . ? C8 H8B 1.01(2) . ? C8 H8C 0.99(2) . ? C9 H9A 1.01(2) . ? C9 H9B 0.95(2) . ? C9 H9C 0.98(2) . ? C10 H10A 0.97(2) . ? C10 H10B 0.99(2) . ? C10 H10C 1.01(2) . ? C11 C12 1.383(3) . ? C11 C16 1.385(2) . ? C11 S1 1.7595(17) . ? C12 C13 1.385(3) . ? C12 H12 0.95(2) . ? C13 C14 1.383(3) . ? C13 H13 0.91(3) . ? C14 C15 1.382(3) . ? C14 C17 1.512(3) . ? C15 C16 1.392(3) . ? C15 H15 0.98(2) . ? C16 H16 0.98(2) . ? C17 H17A 0.92(5) . ? C17 H17B 1.02(5) . ? C17 H17C 0.94(4) . ? O1 S1 1.5660(11) . ? O2 S1 1.4283(13) . ? 03 S1 1.4286(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 106.14(12) . . ? O1 C1 C6 108.36(12) . . ? C2 C1 C6 112.69(13) . . ? O1 C1 H1 106.3(10) . . ? C2 C1 H1 110.2(11) . . ? C6 C1 H1 112.7(11) . . ? C1 C2 C3 110.57(13) . . ? C1 C2 H4A 109.2(11) . . ? C3 C2 H4A 111.6(11) . . ? C1 C2 H4B 109.5(11) . . ? C3 C2 H4B 109.4(11) . . ? H4A C2 H4B 106.6(15) . . ? C2 C3 C4 111.88(13) . . ? C2 C3 H3A 110.7(11) . . ? C4 C3 H3A 108.4(12) . . ? C2 C3 H3B 107.8(12) . . ? C4 C3 H3B 109.9(12) . . ? H3A C3 H3B 108.2(17) . . ? C5 C4 C3 108.32(13) . . ? C5 C4 C7 113.50(12) . . ? C3 C4 C7 114.31(12) . . ? C5 C4 H4 109.2(10) . . ? C3 C4 H4 106.6(10) . . ? C7 C4 H4 104.5(10) . . ? C4 C5 C6 111.61(13) . . ? C4 C5 H5A 111.0(13) . . ? C6 C5 H5A 109.9(12) . . ? C4 C5 H5B 110.6(11) . . ? C6 C5 H5B 109.0(11) . . ? H5A C5 H5B 104.5(16) . . ? C1 C6 C5 110.38(13) . . ? C1 C6 H6A 107.6(13) . . ? C5 C6 H6A 111.1(12) . . ? C1 C6 H6B 108.0(11) . . ? C5 C6 H6B 110.2(11) . . ? H6A C6 H6B 109.5(17) . . ? C9 C7 C10 109.03(15) . . ? C9 C7 C8 108.68(14) . . ? C10 C7 C8 107.88(15) . . ? C9 C7 C4 112.09(13) . . ? C10 C7 C4 109.02(13) . . ? C8 C7 C4 110.05(13) . . ? C7 C8 H8A 112.5(13) . . ? C7 C8 H8B 112.9(13) . . ? H8A C8 H8B 110.5(18) . . ? C7 C8 H8C 109.9(12) . . ? H8A C8 H8C 103.2(18) . . ? H8B C8 H8C 107.2(18) . . ? C7 C9 H9A 112.3(12) . . ? C7 C9 H9B 109.7(14) . . ? H9A C9 H9B 109.2(18) . . ? C7 C9 H9C 112.1(12) . . ? H9A C9 H9C 107.9(17) . . ? H9B C9 H9C 105.3(17) . . ? C7 C10 H10A 111.3(14) . . ? C7 C10 H10B 108.6(14) . . ? H10A C10 H10B 105.1(19) . . ? C7 C10 H10C 113.5(13) . . ? H10A C10 H10C 105.4(18) . . ? H10B C10 H10C 112.5(19) . . ? C12 C11 C16 121.06(16) . . ? C12 C11 S1 119.19(14) . . ? C16 C11 S1 119.75(14) . . ? C11 C12 C13 118.66(19) . . ? C11 C12 H12 119.4(14) . . ? C13 C12 H12 121.9(14) . . ? C14 C13 C12 121.7(2) . . ? C14 C13 H13 119.4(16) . . ? C12 C13 H13 118.9(17) . . ? C15 C14 C13 118.47(17) . . ? C15 C14 C17 120.7(2) . . ? C13 C14 C17 120.9(2) . . ? C14 C15 C16 121.16(18) . . ? C14 C15 H15 119.3(13) . . ? C16 C15 H15 119.5(13) . . ? C11 C16 C15 118.88(18) . . ? C11 C16 H16 119.8(13) . . ? C15 C16 H16 121.3(13) . . ? C14 C17 H17A 114(3) . . ? C14 C17 H17B 110(2) . . ? H17A C17 H17B 118(4) . . ? C14 C17 H17C 110(2) . . ? H17A C17 H17C 98(4) . . ? H17B C17 H17C 106(3) . . ? C1 O1 S1 119.34(9) . . ? O2 S1 03 120.00(8) . . ? O2 S1 O1 103.99(7) . . ? 03 S1 O1 110.07(7) . . ? O2 S1 C11 109.19(8) . . ? 03 S1 C11 108.72(8) . . ? O1 S1 C11 103.63(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -172.77(12) . . . . ? C6 C1 C2 C3 -54.31(17) . . . . ? C1 C2 C3 C4 55.99(18) . . . . ? C2 C3 C4 C5 -57.45(17) . . . . ? C2 C3 C4 C7 174.92(13) . . . . ? C3 C4 C5 C6 57.94(17) . . . . ? C7 C4 C5 C6 -173.97(13) . . . . ? O1 C1 C6 C5 171.98(12) . . . . ? C2 C1 C6 C5 54.84(18) . . . . ? C4 C5 C6 C1 -57.04(18) . . . . ? C5 C4 C7 C9 -54.54(18) . . . . ? C3 C4 C7 C9 70.38(17) . . . . ? C5 C4 C7 C10 66.26(18) . . . . ? C3 C4 C7 C10 -168.81(14) . . . . ? C5 C4 C7 C8 -175.61(14) . . . . ? C3 C4 C7 C8 -50.68(18) . . . . ? C16 C11 C12 C13 0.8(3) . . . . ? S1 C11 C12 C13 -178.27(15) . . . . ? C11 C12 C13 C14 0.5(3) . . . . ? C12 C13 C14 C15 -1.6(3) . . . . ? C12 C13 C14 C17 177.51(19) . . . . ? C13 C14 C15 C16 1.4(3) . . . . ? C17 C14 C15 C16 -177.68(17) . . . . ? C12 C11 C16 C15 -0.9(3) . . . . ? S1 C11 C16 C15 178.11(13) . . . . ? C14 C15 C16 C11 -0.2(3) . . . . ? C2 C1 O1 S1 -134.78(11) . . . . ? C6 C1 O1 S1 103.94(13) . . . . ? C1 O1 S1 O2 -171.47(11) . . . . ? C1 O1 S1 03 -41.71(12) . . . . ? C1 O1 S1 C11 74.40(12) . . . . ? C12 C11 S1 O2 -44.93(16) . . . . ? C16 C11 S1 O2 136.01(14) . . . . ? C12 C11 S1 03 -177.52(14) . . . . ? C16 C11 S1 03 3.42(16) . . . . ? C12 C11 S1 O1 65.42(15) . . . . ? C16 C11 S1 O1 -113.64(14) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 69.93 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.356 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.052 data_compound6a _database_code_CSD 205447 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 84-85.5 _chemical_formula_moiety ? _chemical_formula_sum 'C16 H19 N O3' _chemical_formula_weight 273.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.767(2) _cell_length_b 9.556(3) _cell_length_c 10.887(3) _cell_angle_alpha 99.43(3) _cell_angle_beta 90.68(2) _cell_angle_gamma 105.38(2) _cell_volume 668.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 130.0(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 20 _cell_measurement_theta_max 30 _exptl_crystal_description blocks _exptl_crystal_colour yellow _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 0.759 _exptl_absorpt_correction_type Analytical _exptl_absorpt_correction_T_min 0.73 _exptl_absorpt_correction_T_max 0.84 _exptl_absorpt_process_details 'ABSORB Platon' _exptl_special_details ; ? ; _diffrn_ambient_temperature 130.0(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator Nickel-filtered _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method \q2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 9600 _diffrn_standards_decay_% 2 _diffrn_reflns_number 2833 _diffrn_reflns_av_R_equivalents 0.0095 _diffrn_reflns_av_sigmaI/netI 0.0130 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.12 _diffrn_reflns_theta_max 74.89 _reflns_number_total 2689 _reflns_number_gt 2645 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software 5.0 (Enraf-Nonius, 1989)' _computing_cell_refinement ? _computing_data_reduction 'PROCESS_DATA (Gable et al., 1994)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0360P)^2^+0.3026P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.042(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2689 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0359 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0898 _refine_ls_wR_factor_gt 0.0896 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.48825(16) 0.63447(11) 0.69257(10) 0.0182(2) Uani 1 1 d . . . C2 C 0.34849(16) 0.69076(12) 0.78584(10) 0.0175(2) Uani 1 1 d . . . C3 C 0.39468(17) 0.85886(12) 0.79987(10) 0.0196(2) Uani 1 1 d . . . C4 C 0.62073(18) 0.93109(12) 0.84273(11) 0.0241(3) Uani 1 1 d . . . C5 C 0.75913(17) 0.87597(13) 0.74688(11) 0.0237(3) Uani 1 1 d . . . C6 C 0.71412(17) 0.70787(13) 0.73553(11) 0.0224(3) Uani 1 1 d . . . C7 C 0.44371(18) 0.67279(12) 0.56558(10) 0.0206(2) Uani 1 1 d . . . C8 C 0.48815(18) 0.84055(12) 0.57682(10) 0.0212(3) Uani 1 1 d . . . C9 C 0.34885(18) 0.89566(13) 0.67191(11) 0.0229(3) Uani 1 1 d . . . C10 C 0.71411(18) 0.91372(13) 0.61984(11) 0.0244(3) Uani 1 1 d . . . C11 C 0.26685(16) 0.66067(11) 0.99810(10) 0.0176(2) Uani 1 1 d . . . C12 C 0.33363(17) 0.63317(12) 1.11156(10) 0.0203(2) Uani 1 1 d . . . C13 C 0.21936(17) 0.64610(12) 1.21493(10) 0.0208(2) Uani 1 1 d . . . C14 C 0.03772(17) 0.68617(11) 1.20374(10) 0.0197(2) Uani 1 1 d . . . C15 C -0.03125(17) 0.71279(12) 1.09216(11) 0.0208(2) Uani 1 1 d . . . C16 C 0.08340(16) 0.70014(12) 0.98884(10) 0.0202(2) Uani 1 1 d . . . N N -0.08397(15) 0.70039(10) 1.31250(9) 0.0229(2) Uani 1 1 d . . . O1 O 0.38949(12) 0.64466(8) 0.90237(7) 0.0202(2) Uani 1 1 d . . . O2 O -0.03123(15) 0.66393(11) 1.40805(8) 0.0355(2) Uani 1 1 d . . . O3 O -0.23567(13) 0.74666(10) 1.30323(8) 0.0309(2) Uani 1 1 d . . . H1 H 0.457(2) 0.5275(15) 0.6870(12) 0.021(3) Uiso 1 1 d . . . H2 H 0.204(2) 0.6430(14) 0.7589(12) 0.019(3) Uiso 1 1 d . . . H3 H 0.307(2) 0.8952(15) 0.8607(13) 0.023(3) Uiso 1 1 d . . . H4A H 0.647(2) 1.0370(17) 0.8497(13) 0.029(4) Uiso 1 1 d . . . H4B H 0.652(2) 0.9109(16) 0.9268(14) 0.030(4) Uiso 1 1 d . . . H5 H 0.904(2) 0.9211(16) 0.7745(14) 0.031(4) Uiso 1 1 d . . . H6A H 0.747(2) 0.6817(16) 0.8147(14) 0.030(4) Uiso 1 1 d . . . H6B H 0.806(2) 0.6701(16) 0.6750(14) 0.031(4) Uiso 1 1 d . . . H7A H 0.297(2) 0.6230(16) 0.5361(13) 0.029(4) Uiso 1 1 d . . . H7B H 0.532(2) 0.6369(16) 0.5050(13) 0.026(3) Uiso 1 1 d . . . H8 H 0.460(2) 0.8637(15) 0.4951(14) 0.026(3) Uiso 1 1 d . . . H9A H 0.201(2) 0.8500(16) 0.6440(14) 0.030(4) Uiso 1 1 d . . . H9B H 0.371(2) 1.0025(17) 0.6783(14) 0.031(4) Uiso 1 1 d . . . H10A H 0.744(2) 1.0218(16) 0.6253(13) 0.025(3) Uiso 1 1 d . . . H10B H 0.805(2) 0.8794(16) 0.5592(14) 0.029(4) Uiso 1 1 d . . . H12 H 0.459(2) 0.6043(15) 1.1160(13) 0.024(3) Uiso 1 1 d . . . H13 H 0.266(2) 0.6280(16) 1.2921(14) 0.030(4) Uiso 1 1 d . . . H15 H -0.154(2) 0.7409(16) 1.0873(13) 0.027(4) Uiso 1 1 d . . . H18 H 0.035(2) 0.7189(16) 0.9126(14) 0.027(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0227(5) 0.0152(5) 0.0172(5) 0.0029(4) 0.0014(4) 0.0062(4) C2 0.0192(5) 0.0188(5) 0.0149(5) 0.0048(4) 0.0001(4) 0.0049(4) C3 0.0240(5) 0.0177(5) 0.0182(5) 0.0023(4) 0.0042(4) 0.0079(4) C4 0.0283(6) 0.0190(5) 0.0207(6) -0.0009(4) 0.0007(4) 0.0019(4) C5 0.0186(5) 0.0238(6) 0.0254(6) 0.0022(4) 0.0004(4) 0.0012(4) C6 0.0209(5) 0.0266(6) 0.0225(6) 0.0060(4) 0.0019(4) 0.0100(4) C7 0.0268(6) 0.0189(5) 0.0155(5) 0.0016(4) 0.0012(4) 0.0057(4) C8 0.0282(6) 0.0201(5) 0.0175(5) 0.0066(4) 0.0028(4) 0.0085(4) C9 0.0273(6) 0.0214(6) 0.0241(6) 0.0078(4) 0.0035(4) 0.0112(5) C10 0.0276(6) 0.0196(5) 0.0251(6) 0.0051(4) 0.0075(5) 0.0040(4) C11 0.0190(5) 0.0155(5) 0.0171(5) 0.0027(4) 0.0016(4) 0.0023(4) C12 0.0215(5) 0.0204(5) 0.0202(6) 0.0048(4) 0.0006(4) 0.0073(4) C13 0.0252(6) 0.0200(5) 0.0172(5) 0.0047(4) -0.0007(4) 0.0053(4) C14 0.0213(5) 0.0170(5) 0.0185(5) 0.0024(4) 0.0036(4) 0.0017(4) C15 0.0168(5) 0.0212(5) 0.0240(6) 0.0051(4) 0.0007(4) 0.0038(4) C16 0.0189(5) 0.0229(5) 0.0181(5) 0.0057(4) -0.0015(4) 0.0033(4) N 0.0239(5) 0.0221(5) 0.0211(5) 0.0031(4) 0.0036(4) 0.0038(4) O1 0.0227(4) 0.0249(4) 0.0160(4) 0.0071(3) 0.0030(3) 0.0095(3) O2 0.0388(5) 0.0530(6) 0.0205(5) 0.0132(4) 0.0076(4) 0.0181(4) O3 0.0290(5) 0.0376(5) 0.0301(5) 0.0066(4) 0.0087(4) 0.0151(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.5259(15) . ? C1 C7 1.5333(15) . ? C1 C6 1.5342(16) . ? C1 H1 0.979(14) . ? C2 O1 1.4561(13) . ? C2 C3 1.5341(15) . ? C2 H2 0.983(14) . ? C3 C4 1.5335(16) . ? C3 C9 1.5390(15) . ? C3 H3 0.979(14) . ? C4 C5 1.5323(17) . ? C4 H4A 0.970(15) . ? C4 H4B 0.998(15) . ? C5 C10 1.5322(17) . ? C5 C6 1.5373(16) . ? C5 H5 0.981(16) . ? C6 H6A 0.974(15) . ? C6 H6B 1.001(15) . ? C7 C8 1.5344(15) . ? C7 H7A 1.003(15) . ? C7 H7B 0.976(15) . ? C8 C9 1.5315(16) . ? C8 C10 1.5346(17) . ? C8 H8 0.979(15) . ? C9 H9A 1.001(16) . ? C9 H9B 0.983(15) . ? C10 H10A 0.990(14) . ? C10 H10B 0.984(15) . ? C11 O1 1.3542(13) . ? C11 C16 1.3970(16) . ? C11 C12 1.3983(15) . ? C12 C13 1.3804(16) . ? C12 H12 0.964(14) . ? C13 C14 1.3905(16) . ? C13 H13 0.951(15) . ? C14 C15 1.3817(16) . ? C14 N 1.4589(15) . ? C15 C16 1.3812(16) . ? C15 H15 0.942(15) . ? C16 H18 0.949(15) . ? N O2 1.2275(13) . ? N O3 1.2298(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C7 108.38(9) . . ? C2 C1 C6 110.15(9) . . ? C7 C1 C6 109.50(9) . . ? C2 C1 H1 107.9(8) . . ? C7 C1 H1 110.3(8) . . ? C6 C1 H1 110.5(8) . . ? O1 C2 C1 105.97(8) . . ? O1 C2 C3 112.00(9) . . ? C1 C2 C3 109.96(9) . . ? O1 C2 H2 107.6(8) . . ? C1 C2 H2 110.3(8) . . ? C3 C2 H2 110.9(8) . . ? C4 C3 C2 110.00(9) . . ? C4 C3 C9 110.07(9) . . ? C2 C3 C9 107.80(9) . . ? C4 C3 H3 109.7(8) . . ? C2 C3 H3 110.0(8) . . ? C9 C3 H3 109.3(8) . . ? C5 C4 C3 109.81(9) . . ? C5 C4 H4A 109.4(9) . . ? C3 C4 H4A 108.5(9) . . ? C5 C4 H4B 110.5(8) . . ? C3 C4 H4B 111.2(9) . . ? H4A C4 H4B 107.3(12) . . ? C10 C5 C4 109.66(10) . . ? C10 C5 C6 109.30(10) . . ? C4 C5 C6 108.79(10) . . ? C10 C5 H5 110.2(9) . . ? C4 C5 H5 110.0(9) . . ? C6 C5 H5 108.8(9) . . ? C1 C6 C5 109.85(9) . . ? C1 C6 H6A 110.6(9) . . ? C5 C6 H6A 110.6(9) . . ? C1 C6 H6B 110.2(9) . . ? C5 C6 H6B 110.0(9) . . ? H6A C6 H6B 105.5(12) . . ? C1 C7 C8 109.55(9) . . ? C1 C7 H7A 109.8(8) . . ? C8 C7 H7A 110.7(8) . . ? C1 C7 H7B 109.1(8) . . ? C8 C7 H7B 109.3(8) . . ? H7A C7 H7B 108.3(12) . . ? C9 C8 C7 108.91(9) . . ? C9 C8 C10 109.89(10) . . ? C7 C8 C10 109.64(9) . . ? C9 C8 H8 110.1(8) . . ? C7 C8 H8 108.8(8) . . ? C10 C8 H8 109.5(8) . . ? C8 C9 C3 109.45(9) . . ? C8 C9 H9A 110.6(9) . . ? C3 C9 H9A 110.4(9) . . ? C8 C9 H9B 110.3(9) . . ? C3 C9 H9B 110.0(9) . . ? H9A C9 H9B 106.0(12) . . ? C5 C10 C8 109.72(9) . . ? C5 C10 H10A 110.3(8) . . ? C8 C10 H10A 109.9(8) . . ? C5 C10 H10B 109.1(8) . . ? C8 C10 H10B 110.6(9) . . ? H10A C10 H10B 107.1(12) . . ? O1 C11 C16 124.40(10) . . ? O1 C11 C12 115.54(9) . . ? C16 C11 C12 120.05(10) . . ? C13 C12 C11 120.11(10) . . ? C13 C12 H12 120.9(8) . . ? C11 C12 H12 119.0(8) . . ? C12 C13 C14 118.87(10) . . ? C12 C13 H13 119.9(9) . . ? C14 C13 H13 121.2(9) . . ? C15 C14 C13 121.79(10) . . ? C15 C14 N 118.92(10) . . ? C13 C14 N 119.29(10) . . ? C16 C15 C14 119.31(10) . . ? C16 C15 H15 120.5(9) . . ? C14 C15 H15 120.1(9) . . ? C15 C16 C11 119.87(10) . . ? C15 C16 H18 118.8(9) . . ? C11 C16 H18 121.3(9) . . ? O2 N O3 123.36(10) . . ? O2 N C14 118.37(10) . . ? O3 N C14 118.26(10) . . ? C11 O1 C2 119.43(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 C1 C2 O1 177.06(8) . . . . ? C6 C1 C2 O1 -63.15(11) . . . . ? C7 C1 C2 C3 -61.71(11) . . . . ? C6 C1 C2 C3 58.08(11) . . . . ? O1 C2 C3 C4 59.34(11) . . . . ? C1 C2 C3 C4 -58.20(11) . . . . ? O1 C2 C3 C9 179.37(8) . . . . ? C1 C2 C3 C9 61.83(11) . . . . ? C2 C3 C4 C5 59.64(12) . . . . ? C9 C3 C4 C5 -59.00(12) . . . . ? C3 C4 C5 C10 59.22(12) . . . . ? C3 C4 C5 C6 -60.27(12) . . . . ? C2 C1 C6 C5 -59.38(12) . . . . ? C7 C1 C6 C5 59.73(12) . . . . ? C10 C5 C6 C1 -59.64(12) . . . . ? C4 C5 C6 C1 60.07(12) . . . . ? C2 C1 C7 C8 60.57(12) . . . . ? C6 C1 C7 C8 -59.62(12) . . . . ? C1 C7 C8 C9 -60.53(12) . . . . ? C1 C7 C8 C10 59.74(12) . . . . ? C7 C8 C9 C3 60.96(12) . . . . ? C10 C8 C9 C3 -59.16(12) . . . . ? C4 C3 C9 C8 58.86(12) . . . . ? C2 C3 C9 C8 -61.12(12) . . . . ? C4 C5 C10 C8 -59.58(12) . . . . ? C6 C5 C10 C8 59.60(12) . . . . ? C9 C8 C10 C5 59.79(12) . . . . ? C7 C8 C10 C5 -59.88(12) . . . . ? O1 C11 C12 C13 -179.85(9) . . . . ? C16 C11 C12 C13 -0.51(16) . . . . ? C11 C12 C13 C14 0.22(16) . . . . ? C12 C13 C14 C15 0.21(16) . . . . ? C12 C13 C14 N -179.89(9) . . . . ? C13 C14 C15 C16 -0.35(17) . . . . ? N C14 C15 C16 179.75(9) . . . . ? C14 C15 C16 C11 0.05(16) . . . . ? O1 C11 C16 C15 179.65(10) . . . . ? C12 C11 C16 C15 0.37(16) . . . . ? C15 C14 N O2 173.63(10) . . . . ? C13 C14 N O2 -6.28(15) . . . . ? C15 C14 N O3 -5.51(15) . . . . ? C13 C14 N O3 174.58(10) . . . . ? C16 C11 O1 C2 9.31(15) . . . . ? C12 C11 O1 C2 -171.39(9) . . . . ? C1 C2 O1 C11 -170.63(8) . . . . ? C3 C2 O1 C11 69.47(12) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 74.89 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.262 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.034 data_compound6b _database_code_CSD 205448 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H18 N2 O6' _chemical_formula_weight 346.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 29.1896(6) _cell_length_b 7.05180(10) _cell_length_c 15.4150(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.7170(10) _cell_angle_gamma 90.00 _cell_volume 3166.34(10) _cell_formula_units_Z 8 _cell_measurement_temperature 130.0(2) _cell_measurement_reflns_used 28281 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130.0(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _diffrn_measurement_method CCD _diffrn_standards_decay_% ? _diffrn_reflns_number 19999 _diffrn_reflns_av_R_equivalents 0.0638 _diffrn_reflns_av_sigmaI/netI 0.0523 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5513 _reflns_number_gt 3957 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0926P)^2^+0.2241P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5513 _refine_ls_number_parameters 451 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0797 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1680 _refine_ls_wR_factor_gt 0.1377 _refine_ls_goodness_of_fit_ref 1.137 _refine_ls_restrained_S_all 1.137 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.16332(5) 0.34452(19) 0.63848(10) 0.0278(4) Uani 1 1 d . . . O2 O 0.20781(5) 0.1177(2) 0.58553(13) 0.0470(5) Uani 1 1 d . . . O3 O 0.17829(5) 0.7574(2) 0.70084(10) 0.0343(4) Uani 1 1 d . . . O4 O 0.16019(5) 0.7205(2) 0.56405(9) 0.0264(4) Uani 1 1 d . . . O5 O 0.34177(5) 0.9811(2) 0.61348(10) 0.0335(4) Uani 1 1 d . . . O6 O 0.38908(5) 0.7444(2) 0.61111(11) 0.0356(4) Uani 1 1 d . . . N1 N 0.18643(6) 0.7037(2) 0.62829(11) 0.0202(4) Uani 1 1 d . . . N2 N 0.35042(6) 0.8105(3) 0.61122(11) 0.0259(4) Uani 1 1 d . . . C1 C 0.09771(8) 0.1855(3) 0.56135(15) 0.0312(6) Uani 1 1 d . . . H1 H 0.1182 0.1421 0.5157 0.037 Uiso 1 1 calc R . . C2 C 0.12534(7) 0.2080(3) 0.64725(16) 0.0289(5) Uani 1 1 d . . . H2 H 0.1383 0.0822 0.6660 0.035 Uiso 1 1 calc R . . C3 C 0.09557(8) 0.2837(3) 0.71676(15) 0.0287(5) Uani 1 1 d . . . H3 H 0.1148 0.3035 0.7721 0.034 Uiso 1 1 calc R . . C4 C 0.07265(8) 0.4703(3) 0.68816(15) 0.0295(5) Uani 1 1 d . . . H4A H 0.0964 0.5673 0.6792 0.035 Uiso 1 1 calc R . . H4B H 0.0532 0.5164 0.7340 0.035 Uiso 1 1 calc R . . C5 C 0.04322(8) 0.4396(3) 0.60358(15) 0.0309(6) Uani 1 1 d . . . H5 H 0.0281 0.5615 0.5850 0.037 Uiso 1 1 calc R . . C6 C 0.07457(8) 0.3723(3) 0.53333(15) 0.0318(6) Uani 1 1 d . . . H6A H 0.0562 0.3541 0.4777 0.038 Uiso 1 1 calc R . . H6B H 0.0982 0.4697 0.5244 0.038 Uiso 1 1 calc R . . C7 C 0.06068(8) 0.0338(3) 0.57497(16) 0.0353(6) Uani 1 1 d . . . H7A H 0.0421 0.0121 0.5198 0.042 Uiso 1 1 calc R . . H7B H 0.0755 -0.0874 0.5930 0.042 Uiso 1 1 calc R . . C8 C 0.02963(7) 0.1014(3) 0.64505(16) 0.0316(6) Uani 1 1 d . . . H8 H 0.0056 0.0034 0.6540 0.038 Uiso 1 1 calc R . . C9 C 0.05873(8) 0.1330(3) 0.73061(16) 0.0365(6) Uani 1 1 d . . . H9A H 0.0388 0.1755 0.7764 0.044 Uiso 1 1 calc R . . H9B H 0.0736 0.0125 0.7498 0.044 Uiso 1 1 calc R . . C10 C 0.00651(8) 0.2889(3) 0.61768(16) 0.0324(6) Uani 1 1 d . . . H10A H -0.0134 0.3318 0.6633 0.039 Uiso 1 1 calc R . . H10B H -0.0129 0.2704 0.5632 0.039 Uiso 1 1 calc R . . C11 C 0.20160(8) 0.2796(3) 0.60793(16) 0.0292(5) Uani 1 1 d . . . C12 C 0.23829(7) 0.4266(3) 0.60507(14) 0.0245(5) Uani 1 1 d . . . C13 C 0.23231(7) 0.6215(3) 0.61717(13) 0.0197(5) Uani 1 1 d . . . C14 C 0.26810(7) 0.7484(3) 0.61905(13) 0.0223(5) Uani 1 1 d . . . H14 H 0.2631 0.8802 0.6269 0.027 Uiso 1 1 calc R . . C15 C 0.31148(7) 0.6775(3) 0.60913(13) 0.0217(5) Uani 1 1 d . . . C16 C 0.31969(7) 0.4873(3) 0.59606(14) 0.0271(5) Uani 1 1 d . . . H16 H 0.3499 0.4422 0.5890 0.032 Uiso 1 1 calc R . . C17 C 0.28277(7) 0.3642(3) 0.59351(15) 0.0293(6) Uani 1 1 d . . . H17 H 0.2879 0.2332 0.5836 0.035 Uiso 1 1 calc R . . O1' O 0.33594(5) 0.3406(2) 0.37032(11) 0.0314(4) Uani 1 1 d . . . O2' O 0.28408(6) 0.1332(2) 0.31145(13) 0.0471(5) Uani 1 1 d . . . O3' O 0.32788(5) 0.7081(2) 0.29230(10) 0.0302(4) Uani 1 1 d . . . O4' O 0.33024(5) 0.7834(2) 0.42827(10) 0.0385(4) Uani 1 1 d . . . O5' O 0.15825(5) 0.9861(2) 0.39295(10) 0.0337(4) Uani 1 1 d . . . O6' O 0.10977(5) 0.7526(2) 0.38658(11) 0.0355(4) Uani 1 1 d . . . N1' N 0.31195(6) 0.7100(2) 0.36337(12) 0.0232(4) Uani 1 1 d . . . N2' N 0.14876(6) 0.8163(3) 0.38824(11) 0.0259(4) Uani 1 1 d . . . C1' C 0.40169(8) 0.2569(4) 0.28477(16) 0.0397(6) Uani 1 1 d . . . H1' H 0.3812 0.2641 0.2303 0.048 Uiso 1 1 calc R . . C2' C 0.37378(8) 0.2036(3) 0.36124(17) 0.0347(6) Uani 1 1 d . . . H2' H 0.3605 0.0742 0.3511 0.042 Uiso 1 1 calc R . . C3' C 0.40343(8) 0.2026(4) 0.44472(16) 0.0384(6) Uani 1 1 d . . . H3' H 0.3841 0.1742 0.4944 0.046 Uiso 1 1 calc R . . C4' C 0.42694(9) 0.3912(4) 0.45967(17) 0.0427(7) Uani 1 1 d . . . H4'1 H 0.4461 0.3879 0.5150 0.051 Uiso 1 1 calc R . . H4'2 H 0.4036 0.4923 0.4639 0.051 Uiso 1 1 calc R . . C5' C 0.45697(8) 0.4346(3) 0.38462(18) 0.0414(7) Uani 1 1 d . . . H5' H 0.4729 0.5587 0.3953 0.050 Uiso 1 1 calc R . . C6' C 0.42600(8) 0.4468(4) 0.30160(17) 0.0420(7) Uani 1 1 d . . . H6'1 H 0.4445 0.4785 0.2520 0.050 Uiso 1 1 calc R . . H6'2 H 0.4030 0.5483 0.3072 0.050 Uiso 1 1 calc R . . C7' C 0.43744(9) 0.0992(4) 0.27699(19) 0.0517(8) Uani 1 1 d . . . H7'1 H 0.4561 0.1254 0.2270 0.062 Uiso 1 1 calc R . . H7'2 H 0.4217 -0.0239 0.2667 0.062 Uiso 1 1 calc R . . C8' C 0.46876(8) 0.0887(3) 0.36121(16) 0.0348(6) Uani 1 1 d . . . H8' H 0.4921 -0.0136 0.3559 0.042 Uiso 1 1 calc R . . C9' C 0.43930(8) 0.0443(4) 0.43702(18) 0.0456(7) Uani 1 1 d . . . H9'1 H 0.4590 0.0356 0.4917 0.055 Uiso 1 1 calc R . . H9'2 H 0.4236 -0.0791 0.4271 0.055 Uiso 1 1 calc R . . C10' C 0.49278(8) 0.2778(3) 0.37629(18) 0.0408(7) Uani 1 1 d . . . H10C H 0.5118 0.3063 0.3271 0.049 Uiso 1 1 calc R . . H10D H 0.5132 0.2718 0.4301 0.049 Uiso 1 1 calc R . . C11' C 0.29409(8) 0.2858(3) 0.34308(16) 0.0293(5) Uani 1 1 d . . . C12' C 0.25812(7) 0.4321(3) 0.35710(14) 0.0246(5) Uani 1 1 d . . . C13' C 0.26597(7) 0.6263(3) 0.36978(13) 0.0207(5) Uani 1 1 d . . . C14' C 0.23112(7) 0.7524(3) 0.38293(13) 0.0226(5) Uani 1 1 d . . . H14' H 0.2372 0.8836 0.3919 0.027 Uiso 1 1 calc R . . C15' C 0.18708(7) 0.6817(3) 0.38265(13) 0.0212(5) Uani 1 1 d . . . C16' C 0.17718(7) 0.4910(3) 0.37264(14) 0.0260(5) Uani 1 1 d . . . H16' H 0.1466 0.4455 0.3746 0.031 Uiso 1 1 calc R . . C17' C 0.21318(7) 0.3683(3) 0.35971(15) 0.0280(5) Uani 1 1 d . . . H17' H 0.2070 0.2368 0.3524 0.034 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0164(8) 0.0209(8) 0.0467(10) 0.0019(7) 0.0060(7) 0.0009(6) O2 0.0290(10) 0.0245(9) 0.0889(15) -0.0084(9) 0.0149(9) -0.0007(8) O3 0.0315(10) 0.0489(10) 0.0230(9) -0.0084(8) 0.0060(7) 0.0057(8) O4 0.0231(8) 0.0299(8) 0.0259(8) 0.0026(7) 0.0003(7) 0.0040(7) O5 0.0307(9) 0.0248(9) 0.0452(11) 0.0027(7) 0.0034(8) -0.0033(7) O6 0.0167(9) 0.0413(10) 0.0487(11) -0.0028(8) 0.0015(7) 0.0001(8) N1 0.0201(10) 0.0192(9) 0.0213(10) 0.0016(8) 0.0009(8) -0.0006(8) N2 0.0227(11) 0.0314(11) 0.0236(10) 0.0003(8) 0.0022(8) -0.0027(9) C1 0.0241(13) 0.0332(13) 0.0375(14) -0.0113(11) 0.0111(10) -0.0024(10) C2 0.0209(12) 0.0189(11) 0.0468(15) 0.0029(10) 0.0020(10) -0.0013(10) C3 0.0256(12) 0.0334(13) 0.0269(13) 0.0048(10) 0.0015(10) -0.0041(11) C4 0.0260(12) 0.0293(12) 0.0341(13) -0.0072(10) 0.0083(10) -0.0013(10) C5 0.0248(12) 0.0271(12) 0.0407(14) 0.0007(11) 0.0014(10) 0.0035(10) C6 0.0275(13) 0.0400(14) 0.0277(13) 0.0018(10) -0.0003(10) -0.0071(11) C7 0.0262(13) 0.0307(13) 0.0492(16) -0.0110(11) 0.0048(11) -0.0042(11) C8 0.0190(12) 0.0260(12) 0.0504(16) 0.0007(11) 0.0055(11) -0.0039(10) C9 0.0309(14) 0.0371(14) 0.0420(15) 0.0097(11) 0.0070(11) -0.0053(11) C10 0.0217(12) 0.0337(13) 0.0422(15) -0.0052(11) 0.0044(11) -0.0006(11) C11 0.0217(12) 0.0218(12) 0.0445(15) 0.0011(10) 0.0048(10) 0.0029(10) C12 0.0198(11) 0.0226(11) 0.0311(13) 0.0010(9) 0.0020(9) 0.0016(10) C13 0.0174(11) 0.0247(11) 0.0172(11) 0.0008(8) 0.0027(8) 0.0034(9) C14 0.0251(12) 0.0213(11) 0.0203(11) 0.0010(9) 0.0007(9) 0.0004(10) C15 0.0196(12) 0.0262(12) 0.0190(11) 0.0025(9) -0.0009(9) -0.0028(10) C16 0.0192(12) 0.0305(13) 0.0320(13) 0.0028(10) 0.0051(9) 0.0029(10) C17 0.0253(13) 0.0227(11) 0.0403(14) 0.0005(10) 0.0057(10) 0.0025(10) O1' 0.0164(8) 0.0222(8) 0.0556(11) 0.0004(7) 0.0016(7) 0.0007(7) O2' 0.0296(10) 0.0347(10) 0.0763(14) -0.0184(9) -0.0016(9) 0.0010(8) O3' 0.0287(9) 0.0332(9) 0.0297(9) 0.0052(7) 0.0100(7) 0.0018(7) O4' 0.0338(10) 0.0553(11) 0.0255(9) 0.0020(8) -0.0047(7) -0.0198(9) O5' 0.0333(10) 0.0252(9) 0.0434(10) 0.0006(7) 0.0087(8) 0.0038(7) O6' 0.0168(9) 0.0418(10) 0.0477(11) -0.0003(8) -0.0004(7) -0.0015(8) N1' 0.0198(10) 0.0244(10) 0.0254(11) 0.0053(8) 0.0015(8) 0.0003(8) N2' 0.0249(11) 0.0305(11) 0.0222(10) 0.0019(8) 0.0020(8) 0.0025(9) C1' 0.0347(14) 0.0533(16) 0.0304(14) -0.0088(12) -0.0048(11) 0.0163(13) C2' 0.0205(12) 0.0181(11) 0.0651(18) 0.0012(11) -0.0014(12) 0.0034(10) C3' 0.0275(13) 0.0509(16) 0.0382(15) 0.0186(12) 0.0130(11) 0.0103(12) C4' 0.0326(15) 0.0592(17) 0.0355(15) -0.0112(13) -0.0049(11) 0.0128(14) C5' 0.0225(13) 0.0296(13) 0.072(2) 0.0007(13) 0.0032(12) -0.0050(11) C6' 0.0341(14) 0.0422(15) 0.0520(17) 0.0203(13) 0.0208(12) 0.0103(12) C7' 0.0438(17) 0.0564(17) 0.0547(19) -0.0172(14) 0.0023(14) 0.0171(14) C8' 0.0207(13) 0.0313(13) 0.0529(16) 0.0038(11) 0.0062(11) 0.0077(11) C9' 0.0272(14) 0.0449(15) 0.0656(19) 0.0240(14) 0.0096(13) 0.0074(12) C10' 0.0245(13) 0.0367(14) 0.0619(18) 0.0083(13) 0.0083(12) 0.0017(12) C11' 0.0238(13) 0.0253(12) 0.0391(14) -0.0001(11) 0.0042(10) -0.0025(10) C12' 0.0224(12) 0.0239(11) 0.0274(12) -0.0012(9) 0.0002(9) 0.0001(10) C13' 0.0168(11) 0.0270(11) 0.0182(11) 0.0034(9) -0.0011(8) -0.0029(9) C14' 0.0263(12) 0.0220(11) 0.0194(11) 0.0003(9) 0.0003(9) -0.0011(10) C15' 0.0193(11) 0.0282(12) 0.0160(11) 0.0016(9) 0.0014(8) 0.0026(10) C16' 0.0208(12) 0.0296(12) 0.0275(12) -0.0002(9) 0.0010(9) -0.0042(10) C17' 0.0233(12) 0.0228(11) 0.0375(14) -0.0013(10) 0.0005(10) -0.0032(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.322(3) . ? O1 C2 1.481(2) . ? O2 C11 1.210(3) . ? O3 N1 1.219(2) . ? O4 N1 1.218(2) . ? O5 N2 1.230(2) . ? O6 N2 1.221(2) . ? N1 C13 1.479(3) . ? N2 C15 1.472(3) . ? C1 C2 1.513(3) . ? C1 C6 1.530(3) . ? C1 C7 1.545(3) . ? C1 H1 1.0000 . ? C2 C3 1.520(3) . ? C2 H2 1.0000 . ? C3 C4 1.528(3) . ? C3 C9 1.537(3) . ? C3 H3 1.0000 . ? C4 C5 1.529(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C10 1.535(3) . ? C5 C6 1.538(3) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.531(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C10 1.531(3) . ? C8 C9 1.538(3) . ? C8 H8 1.0000 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.493(3) . ? C12 C17 1.394(3) . ? C12 C13 1.399(3) . ? C13 C14 1.374(3) . ? C14 C15 1.379(3) . ? C14 H14 0.9500 . ? C15 C16 1.380(3) . ? C16 C17 1.382(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? O1' C11' 1.323(3) . ? O1' C2' 1.481(3) . ? O2' C11' 1.210(3) . ? O3' N1' 1.218(2) . ? O4' N1' 1.218(2) . ? O5' N2' 1.230(2) . ? O6' N2' 1.222(2) . ? N1' C13' 1.475(3) . ? N2' C15' 1.474(3) . ? C1' C2' 1.523(4) . ? C1' C6' 1.530(4) . ? C1' C7' 1.535(3) . ? C1' H1' 1.0000 . ? C2' C3' 1.504(3) . ? C2' H2' 1.0000 . ? C3' C4' 1.508(4) . ? C3' C9' 1.540(3) . ? C3' H3' 1.0000 . ? C4' C5' 1.527(4) . ? C4' H4'1 0.9900 . ? C4' H4'2 0.9900 . ? C5' C6' 1.521(4) . ? C5' C10' 1.532(3) . ? C5' H5' 1.0000 . ? C6' H6'1 0.9900 . ? C6' H6'2 0.9900 . ? C7' C8' 1.540(4) . ? C7' H7'1 0.9900 . ? C7' H7'2 0.9900 . ? C8' C10' 1.518(3) . ? C8' C9' 1.528(3) . ? C8' H8' 1.0000 . ? C9' H9'1 0.9900 . ? C9' H9'2 0.9900 . ? C10' H10C 0.9900 . ? C10' H10D 0.9900 . ? C11' C12' 1.497(3) . ? C12' C17' 1.390(3) . ? C12' C13' 1.400(3) . ? C13' C14' 1.376(3) . ? C14' C15' 1.378(3) . ? C14' H14' 0.9500 . ? C15' C16' 1.382(3) . ? C16' C17' 1.386(3) . ? C16' H16' 0.9500 . ? C17' H17' 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O1 C2 117.54(16) . . ? O4 N1 O3 124.50(18) . . ? O4 N1 C13 118.04(17) . . ? O3 N1 C13 117.38(16) . . ? O6 N2 O5 124.40(18) . . ? O6 N2 C15 117.95(18) . . ? O5 N2 C15 117.65(18) . . ? C2 C1 C6 110.96(18) . . ? C2 C1 C7 106.94(19) . . ? C6 C1 C7 109.56(18) . . ? C2 C1 H1 109.8 . . ? C6 C1 H1 109.8 . . ? C7 C1 H1 109.8 . . ? O1 C2 C1 110.35(18) . . ? O1 C2 C3 107.53(17) . . ? C1 C2 C3 110.91(18) . . ? O1 C2 H2 109.3 . . ? C1 C2 H2 109.3 . . ? C3 C2 H2 109.3 . . ? C2 C3 C4 111.03(18) . . ? C2 C3 C9 106.98(18) . . ? C4 C3 C9 109.77(18) . . ? C2 C3 H3 109.7 . . ? C4 C3 H3 109.7 . . ? C9 C3 H3 109.7 . . ? C3 C4 C5 109.60(18) . . ? C3 C4 H4A 109.8 . . ? C5 C4 H4A 109.8 . . ? C3 C4 H4B 109.8 . . ? C5 C4 H4B 109.8 . . ? H4A C4 H4B 108.2 . . ? C4 C5 C10 109.63(19) . . ? C4 C5 C6 108.48(18) . . ? C10 C5 C6 109.81(18) . . ? C4 C5 H5 109.6 . . ? C10 C5 H5 109.6 . . ? C6 C5 H5 109.6 . . ? C1 C6 C5 109.81(19) . . ? C1 C6 H6A 109.7 . . ? C5 C6 H6A 109.7 . . ? C1 C6 H6B 109.7 . . ? C5 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? C8 C7 C1 109.38(18) . . ? C8 C7 H7A 109.8 . . ? C1 C7 H7A 109.8 . . ? C8 C7 H7B 109.8 . . ? C1 C7 H7B 109.8 . . ? H7A C7 H7B 108.2 . . ? C7 C8 C10 110.2(2) . . ? C7 C8 C9 109.32(19) . . ? C10 C8 C9 108.68(19) . . ? C7 C8 H8 109.5 . . ? C10 C8 H8 109.5 . . ? C9 C8 H8 109.5 . . ? C3 C9 C8 109.49(19) . . ? C3 C9 H9A 109.8 . . ? C8 C9 H9A 109.8 . . ? C3 C9 H9B 109.8 . . ? C8 C9 H9B 109.8 . . ? H9A C9 H9B 108.2 . . ? C8 C10 C5 109.75(18) . . ? C8 C10 H10A 109.7 . . ? C5 C10 H10A 109.7 . . ? C8 C10 H10B 109.7 . . ? C5 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? O2 C11 O1 125.0(2) . . ? O2 C11 C12 121.7(2) . . ? O1 C11 C12 113.25(18) . . ? C17 C12 C13 116.92(19) . . ? C17 C12 C11 117.42(19) . . ? C13 C12 C11 125.59(19) . . ? C14 C13 C12 122.74(19) . . ? C14 C13 N1 115.81(17) . . ? C12 C13 N1 121.45(18) . . ? C13 C14 C15 117.66(19) . . ? C13 C14 H14 121.2 . . ? C15 C14 H14 121.2 . . ? C14 C15 C16 122.5(2) . . ? C14 C15 N2 118.67(18) . . ? C16 C15 N2 118.79(19) . . ? C15 C16 C17 118.2(2) . . ? C15 C16 H16 120.9 . . ? C17 C16 H16 120.9 . . ? C16 C17 C12 121.9(2) . . ? C16 C17 H17 119.0 . . ? C12 C17 H17 119.0 . . ? C11' O1' C2' 117.27(16) . . ? O3' N1' O4' 124.80(18) . . ? O3' N1' C13' 117.27(17) . . ? O4' N1' C13' 117.84(18) . . ? O6' N2' O5' 124.39(18) . . ? O6' N2' C15' 118.12(17) . . ? O5' N2' C15' 117.47(18) . . ? C2' C1' C6' 110.50(19) . . ? C2' C1' C7' 106.4(2) . . ? C6' C1' C7' 109.7(2) . . ? C2' C1' H1' 110.1 . . ? C6' C1' H1' 110.1 . . ? C7' C1' H1' 110.1 . . ? O1' C2' C3' 108.3(2) . . ? O1' C2' C1' 110.61(18) . . ? C3' C2' C1' 110.88(19) . . ? O1' C2' H2' 109.0 . . ? C3' C2' H2' 109.0 . . ? C1' C2' H2' 109.0 . . ? C2' C3' C4' 110.96(19) . . ? C2' C3' C9' 107.1(2) . . ? C4' C3' C9' 110.3(2) . . ? C2' C3' H3' 109.5 . . ? C4' C3' H3' 109.5 . . ? C9' C3' H3' 109.5 . . ? C3' C4' C5' 109.8(2) . . ? C3' C4' H4'1 109.7 . . ? C5' C4' H4'1 109.7 . . ? C3' C4' H4'2 109.7 . . ? C5' C4' H4'2 109.7 . . ? H4'1 C4' H4'2 108.2 . . ? C6' C5' C4' 108.04(19) . . ? C6' C5' C10' 110.0(2) . . ? C4' C5' C10' 110.3(2) . . ? C6' C5' H5' 109.5 . . ? C4' C5' H5' 109.5 . . ? C10' C5' H5' 109.5 . . ? C5' C6' C1' 109.68(19) . . ? C5' C6' H6'1 109.7 . . ? C1' C6' H6'1 109.7 . . ? C5' C6' H6'2 109.7 . . ? C1' C6' H6'2 109.7 . . ? H6'1 C6' H6'2 108.2 . . ? C1' C7' C8' 109.8(2) . . ? C1' C7' H7'1 109.7 . . ? C8' C7' H7'1 109.7 . . ? C1' C7' H7'2 109.7 . . ? C8' C7' H7'2 109.7 . . ? H7'1 C7' H7'2 108.2 . . ? C10' C8' C9' 109.9(2) . . ? C10' C8' C7' 109.3(2) . . ? C9' C8' C7' 108.8(2) . . ? C10' C8' H8' 109.6 . . ? C9' C8' H8' 109.6 . . ? C7' C8' H8' 109.6 . . ? C8' C9' C3' 109.24(19) . . ? C8' C9' H9'1 109.8 . . ? C3' C9' H9'1 109.8 . . ? C8' C9' H9'2 109.8 . . ? C3' C9' H9'2 109.8 . . ? H9'1 C9' H9'2 108.3 . . ? C8' C10' C5' 109.62(19) . . ? C8' C10' H10C 109.7 . . ? C5' C10' H10C 109.7 . . ? C8' C10' H10D 109.7 . . ? C5' C10' H10D 109.7 . . ? H10C C10' H10D 108.2 . . ? O2' C11' O1' 125.6(2) . . ? O2' C11' C12' 121.2(2) . . ? O1' C11' C12' 113.24(18) . . ? C17' C12' C13' 117.30(19) . . ? C17' C12' C11' 116.95(19) . . ? C13' C12' C11' 125.73(19) . . ? C14' C13' C12' 122.48(19) . . ? C14' C13' N1' 115.83(18) . . ? C12' C13' N1' 121.54(19) . . ? C13' C14' C15' 117.63(19) . . ? C13' C14' H14' 121.2 . . ? C15' C14' H14' 121.2 . . ? C14' C15' C16' 122.7(2) . . ? C14' C15' N2' 118.56(18) . . ? C16' C15' N2' 118.63(19) . . ? C15' C16' C17' 118.0(2) . . ? C15' C16' H16' 121.0 . . ? C17' C16' H16' 121.0 . . ? C16' C17' C12' 121.9(2) . . ? C16' C17' H17' 119.1 . . ? C12' C17' H17' 119.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 O1 C2 C1 -83.5(2) . . . . ? C11 O1 C2 C3 155.38(19) . . . . ? C6 C1 C2 O1 -63.5(2) . . . . ? C7 C1 C2 O1 177.06(16) . . . . ? C6 C1 C2 C3 55.6(2) . . . . ? C7 C1 C2 C3 -63.9(2) . . . . ? O1 C2 C3 C4 64.9(2) . . . . ? C1 C2 C3 C4 -55.9(2) . . . . ? O1 C2 C3 C9 -175.37(16) . . . . ? C1 C2 C3 C9 63.9(2) . . . . ? C2 C3 C4 C5 58.8(2) . . . . ? C9 C3 C4 C5 -59.3(2) . . . . ? C3 C4 C5 C10 59.3(2) . . . . ? C3 C4 C5 C6 -60.6(2) . . . . ? C2 C1 C6 C5 -58.3(2) . . . . ? C7 C1 C6 C5 59.6(2) . . . . ? C4 C5 C6 C1 60.5(2) . . . . ? C10 C5 C6 C1 -59.3(2) . . . . ? C2 C1 C7 C8 60.8(2) . . . . ? C6 C1 C7 C8 -59.5(2) . . . . ? C1 C7 C8 C10 59.4(2) . . . . ? C1 C7 C8 C9 -59.9(2) . . . . ? C2 C3 C9 C8 -60.5(2) . . . . ? C4 C3 C9 C8 60.1(2) . . . . ? C7 C8 C9 C3 60.0(2) . . . . ? C10 C8 C9 C3 -60.3(2) . . . . ? C7 C8 C10 C5 -59.2(2) . . . . ? C9 C8 C10 C5 60.5(2) . . . . ? C4 C5 C10 C8 -60.3(2) . . . . ? C6 C5 C10 C8 58.8(2) . . . . ? C2 O1 C11 O2 1.0(3) . . . . ? C2 O1 C11 C12 -177.66(17) . . . . ? O2 C11 C12 C17 -13.3(3) . . . . ? O1 C11 C12 C17 165.4(2) . . . . ? O2 C11 C12 C13 170.0(2) . . . . ? O1 C11 C12 C13 -11.3(3) . . . . ? C17 C12 C13 C14 -0.9(3) . . . . ? C11 C12 C13 C14 175.9(2) . . . . ? C17 C12 C13 N1 178.76(19) . . . . ? C11 C12 C13 N1 -4.5(3) . . . . ? O4 N1 C13 C14 103.6(2) . . . . ? O3 N1 C13 C14 -73.4(2) . . . . ? O4 N1 C13 C12 -76.1(2) . . . . ? O3 N1 C13 C12 107.0(2) . . . . ? C12 C13 C14 C15 -0.5(3) . . . . ? N1 C13 C14 C15 179.85(18) . . . . ? C13 C14 C15 C16 1.2(3) . . . . ? C13 C14 C15 N2 -179.79(17) . . . . ? O6 N2 C15 C14 172.82(19) . . . . ? O5 N2 C15 C14 -6.8(3) . . . . ? O6 N2 C15 C16 -8.1(3) . . . . ? O5 N2 C15 C16 172.29(18) . . . . ? C14 C15 C16 C17 -0.4(3) . . . . ? N2 C15 C16 C17 -179.47(19) . . . . ? C15 C16 C17 C12 -1.0(3) . . . . ? C13 C12 C17 C16 1.7(3) . . . . ? C11 C12 C17 C16 -175.4(2) . . . . ? C11' O1' C2' C3' -134.8(2) . . . . ? C11' O1' C2' C1' 103.5(2) . . . . ? C6' C1' C2' O1' 65.0(2) . . . . ? C7' C1' C2' O1' -175.92(18) . . . . ? C6' C1' C2' C3' -55.1(2) . . . . ? C7' C1' C2' C3' 63.9(2) . . . . ? O1' C2' C3' C4' -65.5(2) . . . . ? C1' C2' C3' C4' 56.0(3) . . . . ? O1' C2' C3' C9' 174.10(18) . . . . ? C1' C2' C3' C9' -64.4(2) . . . . ? C2' C3' C4' C5' -59.7(3) . . . . ? C9' C3' C4' C5' 58.8(3) . . . . ? C3' C4' C5' C6' 61.8(3) . . . . ? C3' C4' C5' C10' -58.5(3) . . . . ? C4' C5' C6' C1' -61.0(3) . . . . ? C10' C5' C6' C1' 59.5(3) . . . . ? C2' C1' C6' C5' 58.2(3) . . . . ? C7' C1' C6' C5' -58.8(3) . . . . ? C2' C1' C7' C8' -60.7(3) . . . . ? C6' C1' C7' C8' 58.8(3) . . . . ? C1' C7' C8' C10' -59.5(3) . . . . ? C1' C7' C8' C9' 60.5(3) . . . . ? C10' C8' C9' C3' 59.5(3) . . . . ? C7' C8' C9' C3' -60.1(3) . . . . ? C2' C3' C9' C8' 61.5(3) . . . . ? C4' C3' C9' C8' -59.4(3) . . . . ? C9' C8' C10' C5' -59.4(3) . . . . ? C7' C8' C10' C5' 59.9(3) . . . . ? C6' C5' C10' C8' -60.4(3) . . . . ? C4' C5' C10' C8' 58.7(3) . . . . ? C2' O1' C11' O2' 0.1(4) . . . . ? C2' O1' C11' C12' 178.53(19) . . . . ? O2' C11' C12' C17' 20.4(3) . . . . ? O1' C11' C12' C17' -158.1(2) . . . . ? O2' C11' C12' C13' -161.2(2) . . . . ? O1' C11' C12' C13' 20.3(3) . . . . ? C17' C12' C13' C14' -1.1(3) . . . . ? C11' C12' C13' C14' -179.5(2) . . . . ? C17' C12' C13' N1' -176.52(18) . . . . ? C11' C12' C13' N1' 5.1(3) . . . . ? O3' N1' C13' C14' -109.6(2) . . . . ? O4' N1' C13' C14' 67.1(2) . . . . ? O3' N1' C13' C12' 66.1(3) . . . . ? O4' N1' C13' C12' -117.2(2) . . . . ? C12' C13' C14' C15' -0.5(3) . . . . ? N1' C13' C14' C15' 175.15(17) . . . . ? C13' C14' C15' C16' 2.2(3) . . . . ? C13' C14' C15' N2' -174.27(17) . . . . ? O6' N2' C15' C14' 178.87(18) . . . . ? O5' N2' C15' C14' 0.0(3) . . . . ? O6' N2' C15' C16' 2.3(3) . . . . ? O5' N2' C15' C16' -176.60(18) . . . . ? C14' C15' C16' C17' -2.1(3) . . . . ? N2' C15' C16' C17' 174.36(18) . . . . ? C15' C16' C17' C12' 0.3(3) . . . . ? C13' C12' C17' C16' 1.2(3) . . . . ? C11' C12' C17' C16' 179.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.373 _refine_diff_density_min -0.467 _refine_diff_density_rms 0.139 data_compound6c _database_code_CSD 205449 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 68-70 _chemical_formula_moiety ? _chemical_formula_sum 'C17 H19 N O4' _chemical_formula_weight 301.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.539(3) _cell_length_b 8.479(2) _cell_length_c 12.043(3) _cell_angle_alpha 75.30(2) _cell_angle_beta 76.86(2) _cell_angle_gamma 88.83(3) _cell_volume 724.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 130.0(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 15 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.809 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130.0(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method \q2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 9600 _diffrn_standards_decay_% 2 _diffrn_reflns_number 4014 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0169 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.90 _diffrn_reflns_theta_max 73.20 _reflns_number_total 2761 _reflns_number_gt 2635 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software 5.0 (Enraf-Nonius, 1989)' _computing_cell_refinement ? _computing_data_reduction 'PROCESS_DATA (Gable et al., 1994)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0578P)^2^+0.2867P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0173(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2761 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1113 _refine_ls_wR_factor_gt 0.1096 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.30953(12) 0.08925(10) 0.18764(8) 0.0234(2) Uani 1 1 d . . . C14 C 0.21602(16) 0.57349(15) -0.08941(11) 0.0223(3) Uani 1 1 d . . . O3 O 0.27102(16) 0.82751(12) -0.06239(9) 0.0374(3) Uani 1 1 d . . . O2 O 0.35333(18) 0.32809(12) 0.22850(9) 0.0429(3) Uani 1 1 d . . . O4 O 0.16115(16) 0.81940(13) -0.21348(9) 0.0408(3) Uani 1 1 d . . . C2 C 0.36240(17) -0.00098(14) 0.29665(11) 0.0207(3) Uani 1 1 d . . . H2 H 0.4427 0.0706 0.3205 0.025 Uiso 1 1 calc R . . N N 0.21650(15) 0.75318(13) -0.12446(9) 0.0263(3) Uani 1 1 d . . . C12 C 0.26038(16) 0.32898(15) 0.05055(11) 0.0212(3) Uani 1 1 d . . . C7 C 0.52876(17) -0.24008(15) 0.38320(11) 0.0240(3) Uani 1 1 d . . . H7A H 0.5992 -0.3353 0.3681 0.029 Uiso 1 1 calc R . . H7B H 0.6085 -0.1666 0.4044 0.029 Uiso 1 1 calc R . . C10 C 0.24134(19) -0.40879(16) 0.44764(12) 0.0293(3) Uani 1 1 d . . . H10A H 0.1339 -0.4477 0.5135 0.035 Uiso 1 1 calc R . . H10B H 0.3094 -0.5051 0.4324 0.035 Uiso 1 1 calc R . . C5 C 0.17722(19) -0.31698(16) 0.33572(13) 0.0293(3) Uani 1 1 d . . . H5 H 0.0976 -0.3918 0.3142 0.035 Uiso 1 1 calc R . . C11 C 0.31200(18) 0.25105(15) 0.16563(11) 0.0238(3) Uani 1 1 d . . . C1 C 0.46475(17) -0.14847(15) 0.27105(11) 0.0228(3) Uani 1 1 d . . . H1 H 0.5738 -0.1110 0.2045 0.027 Uiso 1 1 calc R . . C13 C 0.26464(16) 0.49866(15) 0.01576(11) 0.0219(3) Uani 1 1 d . . . H13 H 0.2999 0.5618 0.0626 0.026 Uiso 1 1 calc R . . C9 C 0.25948(19) -0.14603(17) 0.50405(11) 0.0282(3) Uani 1 1 d . . . H9A H 0.3389 -0.0721 0.5251 0.034 Uiso 1 1 calc R . . H9B H 0.1525 -0.1807 0.5709 0.034 Uiso 1 1 calc R . . C17 C 0.20717(17) 0.23888(16) -0.02006(11) 0.0240(3) Uani 1 1 d . . . H17 H 0.2043 0.1230 0.0036 0.029 Uiso 1 1 calc R . . C4 C 0.07179(18) -0.16736(17) 0.35736(13) 0.0299(3) Uani 1 1 d . . . H4A H -0.0389 -0.2021 0.4214 0.036 Uiso 1 1 calc R . . H4B H 0.0335 -0.1084 0.2850 0.036 Uiso 1 1 calc R . . C15 C 0.16208(17) 0.48719(17) -0.16110(11) 0.0259(3) Uani 1 1 d . . . H15 H 0.1290 0.5423 -0.2322 0.031 Uiso 1 1 calc R . . C3 C 0.19504(17) -0.05386(16) 0.39200(11) 0.0243(3) Uani 1 1 d . . . H3 H 0.1268 0.0438 0.4071 0.029 Uiso 1 1 calc R . . C6 C 0.3416(2) -0.26165(16) 0.23679(12) 0.0284(3) Uani 1 1 d . . . H6A H 0.3032 -0.2027 0.1644 0.034 Uiso 1 1 calc R . . H6B H 0.4097 -0.3574 0.2204 0.034 Uiso 1 1 calc R . . C8 C 0.36440(17) -0.29572(16) 0.48224(11) 0.0241(3) Uani 1 1 d . . . H8 H 0.4032 -0.3554 0.5552 0.029 Uiso 1 1 calc R . . C16 C 0.15823(18) 0.31823(17) -0.12528(12) 0.0275(3) Uani 1 1 d . . . H16 H 0.1222 0.2559 -0.1723 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0315(5) 0.0148(4) 0.0237(5) -0.0026(3) -0.0088(4) 0.0020(3) C14 0.0205(6) 0.0204(6) 0.0213(6) -0.0012(5) 0.0000(5) 0.0015(5) O3 0.0544(7) 0.0213(5) 0.0357(6) -0.0010(4) -0.0151(5) -0.0043(4) O2 0.0835(9) 0.0181(5) 0.0352(6) -0.0064(4) -0.0310(6) 0.0041(5) O4 0.0584(7) 0.0313(6) 0.0286(5) 0.0051(4) -0.0163(5) 0.0063(5) C2 0.0243(6) 0.0164(6) 0.0217(6) -0.0035(5) -0.0077(5) 0.0018(5) N 0.0280(6) 0.0230(6) 0.0216(5) 0.0015(4) -0.0013(4) 0.0003(4) C12 0.0205(6) 0.0198(6) 0.0209(6) -0.0038(5) -0.0017(5) 0.0015(4) C7 0.0206(6) 0.0202(6) 0.0294(7) -0.0028(5) -0.0060(5) 0.0022(5) C10 0.0285(7) 0.0217(6) 0.0332(7) 0.0036(5) -0.0094(5) -0.0044(5) C5 0.0331(7) 0.0209(6) 0.0354(7) -0.0011(5) -0.0170(6) -0.0057(5) C11 0.0292(7) 0.0167(6) 0.0243(6) -0.0042(5) -0.0049(5) 0.0011(5) C1 0.0245(6) 0.0177(6) 0.0223(6) -0.0022(5) -0.0010(5) 0.0027(5) C13 0.0229(6) 0.0201(6) 0.0213(6) -0.0045(5) -0.0028(5) 0.0002(5) C9 0.0299(7) 0.0328(7) 0.0208(6) -0.0062(5) -0.0042(5) 0.0047(5) C17 0.0235(6) 0.0215(6) 0.0266(6) -0.0077(5) -0.0031(5) 0.0028(5) C4 0.0220(6) 0.0308(7) 0.0334(7) 0.0015(6) -0.0098(5) -0.0012(5) C15 0.0244(6) 0.0315(7) 0.0199(6) -0.0043(5) -0.0039(5) 0.0048(5) C3 0.0239(6) 0.0248(6) 0.0235(6) -0.0060(5) -0.0048(5) 0.0062(5) C6 0.0443(8) 0.0179(6) 0.0251(6) -0.0063(5) -0.0121(6) 0.0048(5) C8 0.0239(6) 0.0245(6) 0.0215(6) 0.0000(5) -0.0071(5) 0.0018(5) C16 0.0283(7) 0.0311(7) 0.0264(7) -0.0131(5) -0.0067(5) 0.0040(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.3293(15) . ? O1 C2 1.4776(15) . ? C14 C13 1.3910(18) . ? C14 C15 1.3924(19) . ? C14 N 1.4740(17) . ? O3 N 1.2305(16) . ? O2 C11 1.2098(17) . ? O4 N 1.2358(15) . ? C2 C3 1.4882(18) . ? C2 C1 1.5175(17) . ? C2 H2 1.0000 . ? C12 C13 1.3915(18) . ? C12 C17 1.4018(18) . ? C12 C11 1.5095(18) . ? C7 C8 1.4989(18) . ? C7 C1 1.5521(17) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C10 C8 1.5389(18) . ? C10 C5 1.5508(18) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C5 C6 1.498(2) . ? C5 C4 1.530(2) . ? C5 H5 1.0000 . ? C1 C6 1.5377(19) . ? C1 H1 1.0000 . ? C13 H13 0.9500 . ? C9 C8 1.5294(19) . ? C9 C3 1.5540(18) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C17 C16 1.4016(19) . ? C17 H17 0.9500 . ? C4 C3 1.5427(19) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C15 C16 1.386(2) . ? C15 H15 0.9500 . ? C3 H3 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C8 H8 1.0000 . ? C16 H16 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O1 C2 116.92(9) . . ? C13 C14 C15 123.31(12) . . ? C13 C14 N 118.08(11) . . ? C15 C14 N 118.58(11) . . ? O1 C2 C3 109.08(10) . . ? O1 C2 C1 107.73(10) . . ? C3 C2 C1 110.24(10) . . ? O1 C2 H2 109.9 . . ? C3 C2 H2 109.9 . . ? C1 C2 H2 109.9 . . ? O3 N O4 124.25(11) . . ? O3 N C14 117.65(11) . . ? O4 N C14 118.10(11) . . ? C13 C12 C17 119.66(12) . . ? C13 C12 C11 117.15(11) . . ? C17 C12 C11 123.18(11) . . ? C8 C7 C1 108.76(10) . . ? C8 C7 H7A 109.9 . . ? C1 C7 H7A 109.9 . . ? C8 C7 H7B 109.9 . . ? C1 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? C8 C10 C5 110.46(10) . . ? C8 C10 H10A 109.6 . . ? C5 C10 H10A 109.6 . . ? C8 C10 H10B 109.6 . . ? C5 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C6 C5 C4 108.82(11) . . ? C6 C5 C10 108.64(11) . . ? C4 C5 C10 110.41(12) . . ? C6 C5 H5 109.6 . . ? C4 C5 H5 109.6 . . ? C10 C5 H5 109.6 . . ? O2 C11 O1 124.65(12) . . ? O2 C11 C12 123.50(11) . . ? O1 C11 C12 111.84(11) . . ? C2 C1 C6 110.52(11) . . ? C2 C1 C7 108.26(10) . . ? C6 C1 C7 110.42(10) . . ? C2 C1 H1 109.2 . . ? C6 C1 H1 109.2 . . ? C7 C1 H1 109.2 . . ? C14 C13 C12 118.28(12) . . ? C14 C13 H13 120.9 . . ? C12 C13 H13 120.9 . . ? C8 C9 C3 110.38(10) . . ? C8 C9 H9A 109.6 . . ? C3 C9 H9A 109.6 . . ? C8 C9 H9B 109.6 . . ? C3 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C16 C17 C12 120.57(12) . . ? C16 C17 H17 119.7 . . ? C12 C17 H17 119.7 . . ? C5 C4 C3 109.22(11) . . ? C5 C4 H4A 109.8 . . ? C3 C4 H4A 109.8 . . ? C5 C4 H4B 109.8 . . ? C3 C4 H4B 109.8 . . ? H4A C4 H4B 108.3 . . ? C16 C15 C14 117.78(12) . . ? C16 C15 H15 121.1 . . ? C14 C15 H15 121.1 . . ? C2 C3 C4 110.45(11) . . ? C2 C3 C9 106.61(10) . . ? C4 C3 C9 110.38(11) . . ? C2 C3 H3 109.8 . . ? C4 C3 H3 109.8 . . ? C9 C3 H3 109.8 . . ? C5 C6 C1 109.43(11) . . ? C5 C6 H6A 109.8 . . ? C1 C6 H6A 109.8 . . ? C5 C6 H6B 109.8 . . ? C1 C6 H6B 109.8 . . ? H6A C6 H6B 108.2 . . ? C7 C8 C9 108.68(11) . . ? C7 C8 C10 109.33(11) . . ? C9 C8 C10 109.34(11) . . ? C7 C8 H8 109.8 . . ? C9 C8 H8 109.8 . . ? C10 C8 H8 109.8 . . ? C15 C16 C17 120.39(12) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 O1 C2 C3 96.03(13) . . . . ? C11 O1 C2 C1 -144.31(11) . . . . ? C13 C14 N O3 4.47(17) . . . . ? C15 C14 N O3 -177.36(11) . . . . ? C13 C14 N O4 -175.03(11) . . . . ? C15 C14 N O4 3.15(17) . . . . ? C8 C10 C5 C6 60.11(15) . . . . ? C8 C10 C5 C4 -59.15(14) . . . . ? C2 O1 C11 O2 -0.37(19) . . . . ? C2 O1 C11 C12 178.47(9) . . . . ? C13 C12 C11 O2 1.16(19) . . . . ? C17 C12 C11 O2 -177.95(13) . . . . ? C13 C12 C11 O1 -177.69(10) . . . . ? C17 C12 C11 O1 3.19(17) . . . . ? O1 C2 C1 C6 -61.49(12) . . . . ? C3 C2 C1 C6 57.44(13) . . . . ? O1 C2 C1 C7 177.47(9) . . . . ? C3 C2 C1 C7 -63.60(13) . . . . ? C8 C7 C1 C2 61.23(13) . . . . ? C8 C7 C1 C6 -59.88(13) . . . . ? C15 C14 C13 C12 0.48(18) . . . . ? N C14 C13 C12 178.56(10) . . . . ? C17 C12 C13 C14 -0.26(18) . . . . ? C11 C12 C13 C14 -179.41(10) . . . . ? C13 C12 C17 C16 -0.02(18) . . . . ? C11 C12 C17 C16 179.07(11) . . . . ? C6 C5 C4 C3 -60.75(14) . . . . ? C10 C5 C4 C3 58.41(14) . . . . ? C13 C14 C15 C16 -0.40(19) . . . . ? N C14 C15 C16 -178.47(11) . . . . ? O1 C2 C3 C4 60.62(13) . . . . ? C1 C2 C3 C4 -57.48(13) . . . . ? O1 C2 C3 C9 -179.44(9) . . . . ? C1 C2 C3 C9 62.46(13) . . . . ? C5 C4 C3 C2 59.33(14) . . . . ? C5 C4 C3 C9 -58.32(14) . . . . ? C8 C9 C3 C2 -61.05(14) . . . . ? C8 C9 C3 C4 58.94(14) . . . . ? C4 C5 C6 C1 60.80(14) . . . . ? C10 C5 C6 C1 -59.46(13) . . . . ? C2 C1 C6 C5 -59.36(14) . . . . ? C7 C1 C6 C5 60.40(13) . . . . ? C1 C7 C8 C9 -60.05(13) . . . . ? C1 C7 C8 C10 59.23(13) . . . . ? C3 C9 C8 C7 60.95(14) . . . . ? C3 C9 C8 C10 -58.33(14) . . . . ? C5 C10 C8 C7 -60.43(14) . . . . ? C5 C10 C8 C9 58.45(14) . . . . ? C14 C15 C16 C17 0.09(19) . . . . ? C12 C17 C16 C15 0.11(19) . . . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 73.20 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 0.307 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.045 data_compound6d _database_code_CSD 205450 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 79-82 _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 O3 S' _chemical_formula_weight 292.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.7354(9) _cell_length_b 11.1250(10) _cell_length_c 11.1320(10) _cell_angle_alpha 90.00 _cell_angle_beta 104.382(7) _cell_angle_gamma 90.00 _cell_volume 1407.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 130.0(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 20 _cell_measurement_theta_max 25 _exptl_crystal_description blocks _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 2.084 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.57 _exptl_absorpt_correction_T_max 0.83 _exptl_absorpt_process_details 'ABSORB Platon' _exptl_special_details ; ? ; _diffrn_ambient_temperature 130.0(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator Nickel-Filtered _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method \q2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 9600 _diffrn_standards_decay_% 2 _diffrn_reflns_number 3055 _diffrn_reflns_av_R_equivalents 0.0142 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.89 _diffrn_reflns_theta_max 74.91 _reflns_number_total 2900 _reflns_number_gt 2612 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software 5.0 (Enraf-Nonius, 1989)' _computing_cell_refinement ? _computing_data_reduction 'PROCESS_DATA (Gable et al., 1994)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0389P)^2^+0.7011P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0025(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2900 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0813 _refine_ls_wR_factor_gt 0.0781 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.13972(13) -0.10620(13) -0.08817(12) 0.0207(3) Uani 1 1 d . . . C2 C 0.23321(12) -0.01858(12) -0.10580(12) 0.0183(3) Uani 1 1 d . . . C3 C 0.23000(12) -0.00245(12) -0.24272(12) 0.0188(3) Uani 1 1 d . . . C4 C 0.10692(12) 0.03640(13) -0.31582(13) 0.0215(3) Uani 1 1 d . . . C5 C 0.01565(12) -0.05698(14) -0.30010(13) 0.0225(3) Uani 1 1 d . . . C6 C 0.01731(13) -0.06581(15) -0.16200(13) 0.0240(3) Uani 1 1 d . . . C7 C 0.16999(14) -0.22869(13) -0.13583(13) 0.0236(3) Uani 1 1 d . . . C8 C 0.16886(13) -0.21906(13) -0.27368(13) 0.0223(3) Uani 1 1 d . . . C9 C 0.26014(13) -0.12567(14) -0.28946(13) 0.0220(3) Uani 1 1 d . . . C10 C 0.04600(13) -0.17926(14) -0.34744(13) 0.0247(3) Uani 1 1 d . . . C11 C 0.35395(12) 0.07311(13) 0.17094(13) 0.0202(3) Uani 1 1 d . . . C12 C 0.30312(13) 0.09408(14) 0.26960(14) 0.0242(3) Uani 1 1 d . . . C13 C 0.33447(14) 0.02074(15) 0.37348(14) 0.0290(3) Uani 1 1 d . . . C14 C 0.41379(14) -0.07229(15) 0.37779(14) 0.0291(3) Uani 1 1 d . . . C15 C 0.46411(13) -0.09233(14) 0.27945(15) 0.0284(3) Uani 1 1 d . . . C16 C 0.43523(12) -0.01881(14) 0.17549(14) 0.0242(3) Uani 1 1 d . . . O1 O 0.20991(9) 0.09804(9) -0.05159(9) 0.0229(2) Uani 1 1 d . . . O2 O 0.41346(9) 0.16878(10) -0.01669(10) 0.0277(2) Uani 1 1 d . . . O3 O 0.26537(9) 0.27409(9) 0.06828(10) 0.0274(2) Uani 1 1 d . . . S1 S 0.31536(3) 0.16472(3) 0.03800(3) 0.02025(12) Uani 1 1 d . . . H1 H 0.1426(14) -0.1113(16) 0.0001(16) 0.024(4) Uiso 1 1 d . . . H2 H 0.3108(14) -0.0455(14) -0.0602(14) 0.016(4) Uiso 1 1 d . . . H3 H 0.2898(14) 0.0571(15) -0.2496(15) 0.017(4) Uiso 1 1 d . . . H4A H 0.1079(15) 0.0436(16) -0.4030(17) 0.028(4) Uiso 1 1 d . . . H4B H 0.0887(14) 0.1143(16) -0.2872(15) 0.019(4) Uiso 1 1 d . . . H5 H -0.0622(15) -0.0330(16) -0.3480(16) 0.027(4) Uiso 1 1 d . . . H6A H -0.0396(15) -0.1256(16) -0.1487(16) 0.026(4) Uiso 1 1 d . . . H6B H -0.0041(15) 0.0121(17) -0.1328(17) 0.027(4) Uiso 1 1 d . . . H7A H 0.2487(16) -0.2563(16) -0.0878(17) 0.028(4) Uiso 1 1 d . . . H7B H 0.1132(16) -0.2873(17) -0.1236(17) 0.030(5) Uiso 1 1 d . . . H8 H 0.1892(14) -0.2975(16) -0.3014(15) 0.022(4) Uiso 1 1 d . . . H9A H 0.2631(16) -0.1183(17) -0.3749(18) 0.032(5) Uiso 1 1 d . . . H9B H 0.3403(15) -0.1516(15) -0.2434(16) 0.023(4) Uiso 1 1 d . . . H10A H 0.0445(16) -0.1739(16) -0.4333(18) 0.030(5) Uiso 1 1 d . . . H10B H -0.0118(17) -0.2389(17) -0.3382(17) 0.032(5) Uiso 1 1 d . . . H12 H 0.2520(15) 0.1602(16) 0.2650(16) 0.025(4) Uiso 1 1 d . . . H13 H 0.3021(16) 0.0348(17) 0.4433(18) 0.031(5) Uiso 1 1 d . . . H14 H 0.4365(17) -0.1208(18) 0.4493(18) 0.037(5) Uiso 1 1 d . . . H15 H 0.5218(17) -0.1547(17) 0.2830(18) 0.034(5) Uiso 1 1 d . . . H16 H 0.4729(16) -0.0329(17) 0.1083(18) 0.035(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0276(7) 0.0221(7) 0.0128(6) 0.0012(5) 0.0058(5) 0.0002(6) C2 0.0204(6) 0.0160(6) 0.0167(6) -0.0034(5) 0.0011(5) 0.0036(5) C3 0.0196(6) 0.0191(7) 0.0181(6) 0.0009(5) 0.0056(5) -0.0007(5) C4 0.0245(7) 0.0220(7) 0.0173(6) 0.0038(5) 0.0039(5) 0.0024(6) C5 0.0184(6) 0.0286(8) 0.0187(6) 0.0022(6) 0.0017(5) 0.0006(6) C6 0.0219(7) 0.0302(8) 0.0213(7) 0.0003(6) 0.0081(5) -0.0015(6) C7 0.0325(8) 0.0176(7) 0.0192(7) 0.0023(5) 0.0039(6) -0.0013(6) C8 0.0292(7) 0.0190(7) 0.0176(7) -0.0035(5) 0.0039(5) 0.0006(6) C9 0.0233(7) 0.0252(7) 0.0183(7) -0.0025(6) 0.0064(5) 0.0025(6) C10 0.0265(7) 0.0280(8) 0.0177(7) -0.0026(6) 0.0016(5) -0.0058(6) C11 0.0169(6) 0.0211(7) 0.0206(6) -0.0039(5) 0.0009(5) -0.0034(5) C12 0.0208(7) 0.0262(7) 0.0246(7) -0.0067(6) 0.0037(5) -0.0021(6) C13 0.0281(8) 0.0356(9) 0.0225(7) -0.0047(6) 0.0046(6) -0.0080(6) C14 0.0258(7) 0.0315(8) 0.0248(7) 0.0024(6) -0.0037(6) -0.0084(6) C15 0.0207(7) 0.0269(8) 0.0330(8) 0.0000(6) -0.0018(6) 0.0000(6) C16 0.0173(6) 0.0274(8) 0.0264(7) -0.0031(6) 0.0025(5) -0.0003(6) O1 0.0231(5) 0.0196(5) 0.0226(5) -0.0064(4) -0.0006(4) 0.0046(4) O2 0.0302(6) 0.0247(5) 0.0309(6) -0.0023(4) 0.0126(4) -0.0030(4) O3 0.0336(6) 0.0184(5) 0.0291(5) -0.0060(4) 0.0060(4) 0.0037(4) S1 0.02201(18) 0.01699(18) 0.02114(18) -0.00421(12) 0.00420(13) 0.00013(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.5164(19) . ? C1 C6 1.534(2) . ? C1 C7 1.536(2) . ? C1 H1 0.977(17) . ? C2 O1 1.4847(15) . ? C2 C3 1.5259(18) . ? C2 H2 0.973(16) . ? C3 C4 1.5334(18) . ? C3 C9 1.5384(19) . ? C3 H3 0.981(16) . ? C4 C5 1.533(2) . ? C4 H4A 0.976(18) . ? C4 H4B 0.966(17) . ? C5 C10 1.532(2) . ? C5 C6 1.5358(19) . ? C5 H5 0.974(18) . ? C6 H6A 0.979(18) . ? C6 H6B 0.980(19) . ? C7 C8 1.5351(19) . ? C7 H7A 0.994(18) . ? C7 H7B 0.966(19) . ? C8 C9 1.533(2) . ? C8 C10 1.537(2) . ? C8 H8 0.975(18) . ? C9 H9A 0.963(19) . ? C9 H9B 0.995(17) . ? C10 H10A 0.953(19) . ? C10 H10B 0.972(19) . ? C11 C16 1.391(2) . ? C11 C12 1.394(2) . ? C11 S1 1.7609(15) . ? C12 C13 1.388(2) . ? C12 H12 0.942(18) . ? C13 C14 1.385(2) . ? C13 H13 0.960(19) . ? C14 C15 1.385(2) . ? C14 H14 0.94(2) . ? C15 C16 1.389(2) . ? C15 H15 0.963(19) . ? C16 H16 0.971(19) . ? O1 S1 1.5695(10) . ? O2 S1 1.4305(11) . ? O3 S1 1.4270(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 110.71(11) . . ? C2 C1 C7 106.79(11) . . ? C6 C1 C7 109.93(12) . . ? C2 C1 H1 108.8(10) . . ? C6 C1 H1 110.5(10) . . ? C7 C1 H1 110.1(10) . . ? O1 C2 C1 107.27(11) . . ? O1 C2 C3 109.99(11) . . ? C1 C2 C3 111.46(11) . . ? O1 C2 H2 107.4(9) . . ? C1 C2 H2 110.4(9) . . ? C3 C2 H2 110.1(9) . . ? C2 C3 C4 110.46(11) . . ? C2 C3 C9 106.40(11) . . ? C4 C3 C9 109.70(11) . . ? C2 C3 H3 108.4(9) . . ? C4 C3 H3 111.4(9) . . ? C9 C3 H3 110.3(9) . . ? C3 C4 C5 109.95(11) . . ? C3 C4 H4A 108.0(10) . . ? C5 C4 H4A 110.5(10) . . ? C3 C4 H4B 109.5(10) . . ? C5 C4 H4B 110.6(10) . . ? H4A C4 H4B 108.2(14) . . ? C10 C5 C4 109.49(12) . . ? C10 C5 C6 109.95(12) . . ? C4 C5 C6 108.79(12) . . ? C10 C5 H5 108.8(10) . . ? C4 C5 H5 109.8(10) . . ? C6 C5 H5 110.0(10) . . ? C1 C6 C5 109.41(11) . . ? C1 C6 H6A 107.7(10) . . ? C5 C6 H6A 110.8(10) . . ? C1 C6 H6B 111.4(10) . . ? C5 C6 H6B 109.6(10) . . ? H6A C6 H6B 108.0(14) . . ? C8 C7 C1 109.76(11) . . ? C8 C7 H7A 109.6(10) . . ? C1 C7 H7A 110.6(11) . . ? C8 C7 H7B 110.7(11) . . ? C1 C7 H7B 108.9(11) . . ? H7A C7 H7B 107.2(15) . . ? C9 C8 C7 109.21(11) . . ? C9 C8 C10 109.45(12) . . ? C7 C8 C10 109.17(12) . . ? C9 C8 H8 109.7(10) . . ? C7 C8 H8 108.2(10) . . ? C10 C8 H8 111.1(10) . . ? C8 C9 C3 109.83(11) . . ? C8 C9 H9A 111.6(11) . . ? C3 C9 H9A 109.0(11) . . ? C8 C9 H9B 110.0(10) . . ? C3 C9 H9B 110.5(10) . . ? H9A C9 H9B 105.8(14) . . ? C5 C10 C8 109.84(12) . . ? C5 C10 H10A 110.0(11) . . ? C8 C10 H10A 109.6(11) . . ? C5 C10 H10B 110.0(11) . . ? C8 C10 H10B 109.5(11) . . ? H10A C10 H10B 108.0(15) . . ? C16 C11 C12 121.22(14) . . ? C16 C11 S1 119.15(11) . . ? C12 C11 S1 119.63(11) . . ? C13 C12 C11 118.78(14) . . ? C13 C12 H12 122.5(11) . . ? C11 C12 H12 118.6(11) . . ? C14 C13 C12 120.33(15) . . ? C14 C13 H13 119.5(11) . . ? C12 C13 H13 120.2(11) . . ? C15 C14 C13 120.52(15) . . ? C15 C14 H14 119.2(12) . . ? C13 C14 H14 120.2(12) . . ? C14 C15 C16 120.01(15) . . ? C14 C15 H15 121.1(12) . . ? C16 C15 H15 118.8(12) . . ? C15 C16 C11 119.12(14) . . ? C15 C16 H16 118.9(11) . . ? C11 C16 H16 122.0(11) . . ? C2 O1 S1 118.40(8) . . ? O3 S1 O2 119.68(7) . . ? O3 S1 O1 104.33(6) . . ? O2 S1 O1 109.59(6) . . ? O3 S1 C11 109.27(7) . . ? O2 S1 C11 108.05(7) . . ? O1 S1 C11 104.95(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 O1 64.42(13) . . . . ? C7 C1 C2 O1 -175.93(10) . . . . ? C6 C1 C2 C3 -56.03(15) . . . . ? C7 C1 C2 C3 63.62(14) . . . . ? O1 C2 C3 C4 -63.39(14) . . . . ? C1 C2 C3 C4 55.46(15) . . . . ? O1 C2 C3 C9 177.62(10) . . . . ? C1 C2 C3 C9 -63.54(14) . . . . ? C2 C3 C4 C5 -57.87(15) . . . . ? C9 C3 C4 C5 59.10(14) . . . . ? C3 C4 C5 C10 -59.46(15) . . . . ? C3 C4 C5 C6 60.72(15) . . . . ? C2 C1 C6 C5 58.69(15) . . . . ? C7 C1 C6 C5 -59.06(15) . . . . ? C10 C5 C6 C1 59.06(15) . . . . ? C4 C5 C6 C1 -60.83(15) . . . . ? C2 C1 C7 C8 -60.40(15) . . . . ? C6 C1 C7 C8 59.75(15) . . . . ? C1 C7 C8 C9 59.97(16) . . . . ? C1 C7 C8 C10 -59.67(16) . . . . ? C7 C8 C9 C3 -60.17(15) . . . . ? C10 C8 C9 C3 59.29(14) . . . . ? C2 C3 C9 C8 60.43(14) . . . . ? C4 C3 C9 C8 -59.06(14) . . . . ? C4 C5 C10 C8 59.77(15) . . . . ? C6 C5 C10 C8 -59.70(15) . . . . ? C9 C8 C10 C5 -59.78(15) . . . . ? C7 C8 C10 C5 59.70(15) . . . . ? C16 C11 C12 C13 -0.4(2) . . . . ? S1 C11 C12 C13 179.86(11) . . . . ? C11 C12 C13 C14 -0.8(2) . . . . ? C12 C13 C14 C15 0.9(2) . . . . ? C13 C14 C15 C16 0.1(2) . . . . ? C14 C15 C16 C11 -1.2(2) . . . . ? C12 C11 C16 C15 1.3(2) . . . . ? S1 C11 C16 C15 -178.90(11) . . . . ? C1 C2 O1 S1 132.00(10) . . . . ? C3 C2 O1 S1 -106.62(11) . . . . ? C2 O1 S1 O3 177.36(9) . . . . ? C2 O1 S1 O2 48.06(11) . . . . ? C2 O1 S1 C11 -67.75(11) . . . . ? C16 C11 S1 O3 -160.28(11) . . . . ? C12 C11 S1 O3 19.48(13) . . . . ? C16 C11 S1 O2 -28.55(13) . . . . ? C12 C11 S1 O2 151.21(11) . . . . ? C16 C11 S1 O1 88.32(12) . . . . ? C12 C11 S1 O1 -91.92(12) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 74.91 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.349 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.043 data_compound6e _database_code_CSD 205451 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 51-53 _chemical_formula_moiety ? _chemical_formula_sum 'C11 H18 O3 S' _chemical_formula_weight 230.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.000(2) _cell_length_b 9.594(4) _cell_length_c 26.225(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2264.4(12) _cell_formula_units_Z 8 _cell_measurement_temperature 130.0(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 15 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.271 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130.0(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method \q2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 9600 _diffrn_standards_decay_% 2 _diffrn_reflns_number 3002 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2585 _reflns_number_gt 2045 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software 5.0 (Enraf-Nonius, 1989)' _computing_cell_refinement ? _computing_data_reduction 'PROCESS_DATA (Gable et al., 1994)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.5863P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0035(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2585 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.1012 _refine_ls_wR_factor_gt 0.0918 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.35911(5) 0.15131(4) 0.449310(15) 0.01609(14) Uani 1 1 d . . . O1 O 0.22935(14) 0.19579(12) 0.41292(4) 0.0173(3) Uani 1 1 d . . . O2 O 0.42096(15) 0.27963(13) 0.46709(5) 0.0229(3) Uani 1 1 d . . . O3 O 0.45509(14) 0.05531(14) 0.42382(5) 0.0260(3) Uani 1 1 d . . . C1 C -0.0141(2) 0.08775(19) 0.40173(6) 0.0166(3) Uani 1 1 d . . . C2 C 0.1472(2) 0.08658(18) 0.38422(6) 0.0155(3) Uani 1 1 d . . . C3 C 0.1586(2) 0.12333(19) 0.32772(6) 0.0184(4) Uani 1 1 d . . . C4 C 0.0884(2) 0.2662(2) 0.31818(7) 0.0215(4) Uani 1 1 d . . . C5 C -0.0747(2) 0.2650(2) 0.33495(7) 0.0204(4) Uani 1 1 d . . . C6 C -0.0829(2) 0.2304(2) 0.39190(7) 0.0191(4) Uani 1 1 d . . . C7 C -0.0981(2) -0.0234(2) 0.37117(7) 0.0215(4) Uani 1 1 d . . . C8 C -0.0902(2) 0.0110(2) 0.31412(7) 0.0205(4) Uani 1 1 d . . . C9 C 0.0734(2) 0.0118(2) 0.29742(7) 0.0232(4) Uani 1 1 d . . . C10 C -0.1595(2) 0.1544(2) 0.30445(7) 0.0237(4) Uani 1 1 d . . . C11 C 0.2679(2) 0.0665(2) 0.49951(7) 0.0227(4) Uani 1 1 d . . . H1 H -0.013(2) 0.068(2) 0.4386(7) 0.014(5) Uiso 1 1 d . . . H2 H 0.195(2) 0.002(2) 0.3911(7) 0.016(5) Uiso 1 1 d . . . H3 H 0.263(2) 0.118(2) 0.3186(7) 0.022(5) Uiso 1 1 d . . . H4A H 0.146(2) 0.338(2) 0.3368(8) 0.024(5) Uiso 1 1 d . . . H4B H 0.096(2) 0.288(2) 0.2817(9) 0.028(6) Uiso 1 1 d . . . H5 H -0.117(2) 0.353(2) 0.3290(8) 0.024(6) Uiso 1 1 d . . . H6A H -0.034(3) 0.296(2) 0.4116(9) 0.031(6) Uiso 1 1 d . . . H6B H -0.191(2) 0.228(2) 0.4031(7) 0.019(5) Uiso 1 1 d . . . H7A H -0.054(2) -0.118(2) 0.3768(8) 0.023(5) Uiso 1 1 d . . . H7B H -0.204(3) -0.025(2) 0.3819(8) 0.028(6) Uiso 1 1 d . . . H8 H -0.143(2) -0.061(2) 0.2941(8) 0.024(5) Uiso 1 1 d . . . H9A H 0.079(2) 0.036(2) 0.2607(9) 0.028(6) Uiso 1 1 d . . . H9B H 0.113(3) -0.077(3) 0.3021(8) 0.032(6) Uiso 1 1 d . . . H10A H -0.154(2) 0.173(2) 0.2676(9) 0.029(6) Uiso 1 1 d . . . H10B H -0.263(3) 0.156(2) 0.3156(7) 0.022(5) Uiso 1 1 d . . . H11A H 0.344(3) 0.047(2) 0.5242(9) 0.032(6) Uiso 1 1 d . . . H11B H 0.196(3) 0.133(2) 0.5142(8) 0.031(6) Uiso 1 1 d . . . H11C H 0.224(3) -0.011(2) 0.4863(8) 0.028(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0160(2) 0.0142(2) 0.0180(2) -0.00077(15) -0.00383(16) 0.00030(16) O1 0.0201(6) 0.0128(6) 0.0191(6) -0.0002(5) -0.0064(5) 0.0006(5) O2 0.0233(7) 0.0170(7) 0.0284(7) -0.0025(5) -0.0070(6) -0.0037(5) O3 0.0210(7) 0.0279(7) 0.0291(7) -0.0071(6) -0.0038(6) 0.0084(6) C1 0.0187(8) 0.0182(8) 0.0130(7) 0.0008(6) 0.0006(6) -0.0028(7) C2 0.0178(8) 0.0128(8) 0.0158(7) -0.0018(6) -0.0036(7) 0.0002(7) C3 0.0147(8) 0.0245(9) 0.0159(8) -0.0009(7) 0.0012(6) -0.0004(7) C4 0.0217(9) 0.0240(9) 0.0188(8) 0.0058(7) -0.0011(7) -0.0023(8) C5 0.0195(8) 0.0189(9) 0.0229(8) 0.0035(7) -0.0041(7) 0.0037(8) C6 0.0176(8) 0.0197(9) 0.0202(8) -0.0041(7) 0.0003(7) 0.0005(7) C7 0.0234(9) 0.0196(9) 0.0216(8) 0.0003(7) -0.0012(7) -0.0059(8) C8 0.0195(9) 0.0242(9) 0.0178(8) -0.0053(7) -0.0026(7) -0.0038(8) C9 0.0233(9) 0.0299(10) 0.0164(8) -0.0078(8) -0.0005(7) 0.0024(9) C10 0.0178(9) 0.0335(10) 0.0199(9) 0.0002(8) -0.0047(7) 0.0005(8) C11 0.0279(10) 0.0211(9) 0.0190(8) 0.0037(7) -0.0049(8) -0.0052(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O3 1.4287(13) . ? S1 O2 1.4293(13) . ? S1 O1 1.5674(12) . ? S1 C11 1.7519(19) . ? O1 C2 1.487(2) . ? C1 C2 1.522(2) . ? C1 C6 1.525(3) . ? C1 C7 1.534(2) . ? C1 H1 0.984(19) . ? C2 C3 1.527(2) . ? C2 H2 0.94(2) . ? C3 C4 1.530(3) . ? C3 C9 1.537(3) . ? C3 H3 0.97(2) . ? C4 C5 1.532(3) . ? C4 H4A 0.99(2) . ? C4 H4B 0.98(2) . ? C5 C6 1.532(3) . ? C5 C10 1.532(3) . ? C5 H5 0.94(2) . ? C6 H6A 0.92(2) . ? C6 H6B 1.02(2) . ? C7 C8 1.534(2) . ? C7 H7A 1.00(2) . ? C7 H7B 0.99(2) . ? C8 C10 1.531(3) . ? C8 C9 1.536(3) . ? C8 H8 0.99(2) . ? C9 H9A 0.99(2) . ? C9 H9B 0.93(2) . ? C10 H10A 0.98(2) . ? C10 H10B 0.98(2) . ? C11 H11A 0.96(2) . ? C11 H11B 0.99(2) . ? C11 H11C 0.91(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S1 O2 118.19(8) . . ? O3 S1 O1 109.95(7) . . ? O2 S1 O1 104.73(7) . . ? O3 S1 C11 109.62(10) . . ? O2 S1 C11 109.72(9) . . ? O1 S1 C11 103.57(9) . . ? C2 O1 S1 119.13(10) . . ? C2 C1 C6 110.06(14) . . ? C2 C1 C7 107.93(14) . . ? C6 C1 C7 109.59(15) . . ? C2 C1 H1 106.8(11) . . ? C6 C1 H1 109.8(11) . . ? C7 C1 H1 112.6(11) . . ? O1 C2 C1 108.43(13) . . ? O1 C2 C3 107.17(13) . . ? C1 C2 C3 110.78(14) . . ? O1 C2 H2 106.6(12) . . ? C1 C2 H2 112.8(12) . . ? C3 C2 H2 110.8(12) . . ? C2 C3 C4 109.76(14) . . ? C2 C3 C9 107.93(15) . . ? C4 C3 C9 109.45(15) . . ? C2 C3 H3 106.9(12) . . ? C4 C3 H3 113.8(12) . . ? C9 C3 H3 108.8(12) . . ? C3 C4 C5 109.98(15) . . ? C3 C4 H4A 109.1(12) . . ? C5 C4 H4A 111.4(13) . . ? C3 C4 H4B 108.7(13) . . ? C5 C4 H4B 110.6(13) . . ? H4A C4 H4B 106.9(18) . . ? C6 C5 C10 109.59(16) . . ? C6 C5 C4 109.12(15) . . ? C10 C5 C4 109.42(15) . . ? C6 C5 H5 109.6(14) . . ? C10 C5 H5 109.6(13) . . ? C4 C5 H5 109.5(14) . . ? C1 C6 C5 109.85(14) . . ? C1 C6 H6A 109.1(15) . . ? C5 C6 H6A 112.0(15) . . ? C1 C6 H6B 108.7(12) . . ? C5 C6 H6B 109.4(11) . . ? H6A C6 H6B 107.8(19) . . ? C1 C7 C8 109.70(15) . . ? C1 C7 H7A 111.0(12) . . ? C8 C7 H7A 108.7(12) . . ? C1 C7 H7B 109.7(13) . . ? C8 C7 H7B 109.0(12) . . ? H7A C7 H7B 108.7(18) . . ? C10 C8 C7 109.61(15) . . ? C10 C8 C9 109.78(16) . . ? C7 C8 C9 108.91(15) . . ? C10 C8 H8 109.9(12) . . ? C7 C8 H8 110.3(12) . . ? C9 C8 H8 108.4(12) . . ? C8 C9 C3 109.52(15) . . ? C8 C9 H9A 109.0(13) . . ? C3 C9 H9A 108.4(13) . . ? C8 C9 H9B 108.7(14) . . ? C3 C9 H9B 112.4(14) . . ? H9A C9 H9B 108.8(19) . . ? C8 C10 C5 109.46(15) . . ? C8 C10 H10A 107.9(13) . . ? C5 C10 H10A 111.2(13) . . ? C8 C10 H10B 110.5(13) . . ? C5 C10 H10B 108.0(12) . . ? H10A C10 H10B 109.7(18) . . ? S1 C11 H11A 105.5(14) . . ? S1 C11 H11B 107.7(13) . . ? H11A C11 H11B 109.3(18) . . ? S1 C11 H11C 107.4(14) . . ? H11A C11 H11C 114(2) . . ? H11B C11 H11C 113(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 S1 O1 C2 47.32(13) . . . . ? O2 S1 O1 C2 175.28(12) . . . . ? C11 S1 O1 C2 -69.74(13) . . . . ? S1 O1 C2 C1 116.90(13) . . . . ? S1 O1 C2 C3 -123.47(13) . . . . ? C6 C1 C2 O1 59.40(17) . . . . ? C7 C1 C2 O1 178.96(13) . . . . ? C6 C1 C2 C3 -57.95(18) . . . . ? C7 C1 C2 C3 61.62(18) . . . . ? O1 C2 C3 C4 -60.48(18) . . . . ? C1 C2 C3 C4 57.64(19) . . . . ? O1 C2 C3 C9 -179.69(13) . . . . ? C1 C2 C3 C9 -61.57(18) . . . . ? C2 C3 C4 C5 -58.66(19) . . . . ? C9 C3 C4 C5 59.61(19) . . . . ? C3 C4 C5 C6 59.90(19) . . . . ? C3 C4 C5 C10 -60.00(19) . . . . ? C2 C1 C6 C5 59.02(18) . . . . ? C7 C1 C6 C5 -59.53(19) . . . . ? C10 C5 C6 C1 59.84(19) . . . . ? C4 C5 C6 C1 -59.96(19) . . . . ? C2 C1 C7 C8 -60.51(19) . . . . ? C6 C1 C7 C8 59.35(19) . . . . ? C1 C7 C8 C10 -59.5(2) . . . . ? C1 C7 C8 C9 60.6(2) . . . . ? C10 C8 C9 C3 59.55(19) . . . . ? C7 C8 C9 C3 -60.5(2) . . . . ? C2 C3 C9 C8 60.26(19) . . . . ? C4 C3 C9 C8 -59.15(19) . . . . ? C7 C8 C10 C5 59.7(2) . . . . ? C9 C8 C10 C5 -59.92(19) . . . . ? C6 C5 C10 C8 -59.73(19) . . . . ? C4 C5 C10 C8 59.88(19) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.419 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.058 data_compound6f _database_code_CSD 205452 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 68-70 _chemical_formula_moiety ? _chemical_formula_sum 'C17 H22 O3 S' _chemical_formula_weight 306.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.12450(10) _cell_length_b 12.5511(2) _cell_length_c 12.40940(10) _cell_angle_alpha 90.00 _cell_angle_beta 106.8600(10) _cell_angle_gamma 90.00 _cell_volume 1509.13(3) _cell_formula_units_Z 4 _cell_measurement_temperature 130.0(2) _cell_measurement_reflns_used 25493 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plates _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.222 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130.0(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _diffrn_measurement_method CCD _diffrn_standards_decay_% ? _diffrn_reflns_number 24439 _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 28.27 _reflns_number_total 3720 _reflns_number_gt 3276 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0819P)^2^+0.4594P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.017(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3720 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.1199 _refine_ls_wR_factor_gt 0.1143 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.33681(15) 0.00289(10) 0.80756(12) 0.0237(3) Uani 1 1 d . . . H1 H -0.3201 -0.0737 0.8037 0.028 Uiso 1 1 calc R . . C2 C -0.20025(13) 0.06262(10) 0.84117(10) 0.0192(3) Uani 1 1 d . . . H2 H -0.1442 0.0385 0.9155 0.023 Uiso 1 1 calc R . . C3 C -0.22252(14) 0.18247(10) 0.84310(11) 0.0217(3) Uani 1 1 d . . . H3 H -0.1335 0.2195 0.8617 0.026 Uiso 1 1 calc R . . C4 C -0.31472(14) 0.22053(11) 0.72859(12) 0.0261(3) Uani 1 1 d . . . H4A H -0.2697 0.2064 0.6709 0.031 Uiso 1 1 calc R . . H4B H -0.3295 0.2968 0.7310 0.031 Uiso 1 1 calc R . . C5 C -0.45415(14) 0.16234(12) 0.69958(11) 0.0256(3) Uani 1 1 d . . . H5 H -0.5129 0.1874 0.6266 0.031 Uiso 1 1 calc R . . C6 C -0.42877(14) 0.04267(12) 0.69339(12) 0.0273(3) Uani 1 1 d . . . H6A H -0.3842 0.0286 0.6354 0.033 Uiso 1 1 calc R . . H6B H -0.5161 0.0050 0.6738 0.033 Uiso 1 1 calc R . . C7 C -0.40854(15) 0.02543(12) 0.89893(13) 0.0293(3) Uani 1 1 d . . . H7A H -0.4959 -0.0122 0.8812 0.035 Uiso 1 1 calc R . . H7B H -0.3512 0.0001 0.9712 0.035 Uiso 1 1 calc R . . C8 C -0.43332(15) 0.14559(12) 0.90520(12) 0.0279(3) Uani 1 1 d . . . H8 H -0.4788 0.1597 0.9635 0.033 Uiso 1 1 calc R . . C9 C -0.29401(15) 0.20392(12) 0.93461(12) 0.0279(3) Uani 1 1 d . . . H9A H -0.2358 0.1793 1.0069 0.033 Uiso 1 1 calc R . . H9B H -0.3086 0.2799 0.9401 0.033 Uiso 1 1 calc R . . C10 C -0.52548(15) 0.18457(12) 0.79103(12) 0.0279(3) Uani 1 1 d . . . H10A H -0.5423 0.2604 0.7946 0.034 Uiso 1 1 calc R . . H10B H -0.6137 0.1481 0.7727 0.034 Uiso 1 1 calc R . . C11 C 0.08227(12) 0.05965(10) 0.68329(10) 0.0172(2) Uani 1 1 d . . . C12 C 0.14569(13) -0.00828(10) 0.62526(11) 0.0197(3) Uani 1 1 d . . . H12 H 0.1548 -0.0805 0.6426 0.024 Uiso 1 1 calc R . . C13 C 0.19518(13) 0.03337(11) 0.54092(11) 0.0209(3) Uani 1 1 d . . . H13 H 0.2375 -0.0118 0.5015 0.025 Uiso 1 1 calc R . . C14 C 0.18283(13) 0.14154(10) 0.51395(11) 0.0199(3) Uani 1 1 d . . . C15 C 0.11566(13) 0.20778(10) 0.57214(11) 0.0212(3) Uani 1 1 d . . . H15 H 0.1046 0.2797 0.5538 0.025 Uiso 1 1 calc R . . C16 C 0.06525(13) 0.16776(10) 0.65675(11) 0.0200(3) Uani 1 1 d . . . H16 H 0.0209 0.2123 0.6951 0.024 Uiso 1 1 calc R . . C17 C 0.24100(15) 0.18602(12) 0.42431(11) 0.0266(3) Uani 1 1 d . . . H17A H 0.2229 0.2611 0.4166 0.040 Uiso 1 1 calc R . . H17B H 0.1983 0.1512 0.3539 0.040 Uiso 1 1 calc R . . H17C H 0.3388 0.1740 0.4454 0.040 Uiso 1 1 calc R . . O1 O -0.12776(9) 0.03784(8) 0.75525(8) 0.0231(2) Uani 1 1 d . . . O2 O 0.09344(10) 0.07022(8) 0.89678(8) 0.0246(2) Uani 1 1 d . . . O3 O 0.04770(11) -0.10273(8) 0.80225(9) 0.0283(2) Uani 1 1 d . . . S1 S 0.03012(3) 0.01037(2) 0.79671(2) 0.01819(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0222(7) 0.0210(6) 0.0311(7) 0.0000(5) 0.0126(6) -0.0012(5) C2 0.0185(6) 0.0242(6) 0.0169(6) 0.0011(4) 0.0082(5) 0.0011(5) C3 0.0213(6) 0.0220(6) 0.0212(6) -0.0011(5) 0.0054(5) -0.0014(5) C4 0.0278(7) 0.0256(7) 0.0257(7) 0.0077(5) 0.0088(5) 0.0008(5) C5 0.0209(6) 0.0346(7) 0.0199(6) 0.0028(5) 0.0037(5) 0.0040(5) C6 0.0190(6) 0.0356(8) 0.0280(7) -0.0088(6) 0.0079(5) -0.0041(5) C7 0.0273(7) 0.0325(7) 0.0341(8) 0.0095(6) 0.0185(6) 0.0027(6) C8 0.0290(7) 0.0354(8) 0.0237(7) 0.0024(5) 0.0146(6) 0.0084(6) C9 0.0318(7) 0.0299(7) 0.0218(7) -0.0042(5) 0.0074(5) 0.0056(6) C10 0.0228(7) 0.0335(7) 0.0290(7) 0.0010(5) 0.0099(5) 0.0077(5) C11 0.0139(5) 0.0181(6) 0.0194(6) 0.0011(4) 0.0045(4) -0.0001(4) C12 0.0186(6) 0.0165(6) 0.0239(7) 0.0001(4) 0.0058(5) 0.0020(4) C13 0.0196(6) 0.0225(6) 0.0220(6) -0.0016(5) 0.0080(5) 0.0023(5) C14 0.0174(6) 0.0224(6) 0.0189(6) 0.0004(4) 0.0039(5) -0.0013(4) C15 0.0240(6) 0.0173(6) 0.0218(6) 0.0023(4) 0.0059(5) 0.0011(5) C16 0.0217(6) 0.0177(6) 0.0215(6) -0.0008(4) 0.0077(5) 0.0024(4) C17 0.0300(7) 0.0297(7) 0.0218(6) 0.0025(5) 0.0104(5) -0.0025(5) O1 0.0153(4) 0.0368(5) 0.0183(5) -0.0023(4) 0.0065(3) 0.0012(4) O2 0.0227(5) 0.0303(5) 0.0195(5) 0.0003(4) 0.0039(4) -0.0036(4) O3 0.0327(5) 0.0188(5) 0.0366(6) 0.0064(4) 0.0150(4) -0.0004(4) S1 0.01619(19) 0.01909(19) 0.0198(2) 0.00214(10) 0.00606(13) -0.00030(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.5208(18) . ? C1 C6 1.536(2) . ? C1 C7 1.5397(19) . ? C1 H1 0.9800 . ? C2 O1 1.4920(14) . ? C2 C3 1.5223(17) . ? C2 H2 0.9800 . ? C3 C4 1.5328(18) . ? C3 C9 1.5371(18) . ? C3 H3 0.9800 . ? C4 C5 1.5365(19) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.529(2) . ? C5 C10 1.5371(18) . ? C5 H5 0.9800 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.535(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C10 1.533(2) . ? C8 C9 1.536(2) . ? C8 H8 0.9800 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.3878(17) . ? C11 C16 1.3951(17) . ? C11 S1 1.7531(12) . ? C12 C13 1.3871(18) . ? C12 H12 0.9300 . ? C13 C14 1.3951(18) . ? C13 H13 0.9300 . ? C14 C15 1.4000(18) . ? C14 C17 1.5087(17) . ? C15 C16 1.3878(18) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? O1 S1 1.5689(9) . ? O2 S1 1.4336(10) . ? O3 S1 1.4298(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 110.63(11) . . ? C2 C1 C7 107.04(11) . . ? C6 C1 C7 109.29(12) . . ? C2 C1 H1 109.9 . . ? C6 C1 H1 109.9 . . ? C7 C1 H1 109.9 . . ? O1 C2 C1 107.32(10) . . ? O1 C2 C3 108.85(10) . . ? C1 C2 C3 111.37(10) . . ? O1 C2 H2 109.8 . . ? C1 C2 H2 109.8 . . ? C3 C2 H2 109.8 . . ? C2 C3 C4 110.28(11) . . ? C2 C3 C9 106.76(11) . . ? C4 C3 C9 109.86(11) . . ? C2 C3 H3 110.0 . . ? C4 C3 H3 110.0 . . ? C9 C3 H3 110.0 . . ? C3 C4 C5 109.88(11) . . ? C3 C4 H4A 109.7 . . ? C5 C4 H4A 109.7 . . ? C3 C4 H4B 109.7 . . ? C5 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? C6 C5 C4 108.80(11) . . ? C6 C5 C10 109.70(12) . . ? C4 C5 C10 109.71(12) . . ? C6 C5 H5 109.5 . . ? C4 C5 H5 109.5 . . ? C10 C5 H5 109.5 . . ? C5 C6 C1 109.80(11) . . ? C5 C6 H6A 109.7 . . ? C1 C6 H6A 109.7 . . ? C5 C6 H6B 109.7 . . ? C1 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? C8 C7 C1 109.68(11) . . ? C8 C7 H7A 109.7 . . ? C1 C7 H7A 109.7 . . ? C8 C7 H7B 109.7 . . ? C1 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? C10 C8 C7 109.36(12) . . ? C10 C8 C9 109.77(12) . . ? C7 C8 C9 109.15(12) . . ? C10 C8 H8 109.5 . . ? C7 C8 H8 109.5 . . ? C9 C8 H8 109.5 . . ? C8 C9 C3 109.73(11) . . ? C8 C9 H9A 109.7 . . ? C3 C9 H9A 109.7 . . ? C8 C9 H9B 109.7 . . ? C3 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C8 C10 C5 109.51(11) . . ? C8 C10 H10A 109.8 . . ? C5 C10 H10A 109.8 . . ? C8 C10 H10B 109.8 . . ? C5 C10 H10B 109.8 . . ? H10A C10 H10B 108.2 . . ? C12 C11 C16 121.27(12) . . ? C12 C11 S1 119.49(9) . . ? C16 C11 S1 119.17(9) . . ? C13 C12 C11 118.87(11) . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? C12 C13 C14 121.39(12) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C13 C14 C15 118.51(11) . . ? C13 C14 C17 120.66(12) . . ? C15 C14 C17 120.83(12) . . ? C16 C15 C14 121.03(11) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C11 118.90(11) . . ? C15 C16 H16 120.6 . . ? C11 C16 H16 120.6 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C2 O1 S1 118.49(8) . . ? O3 S1 O2 117.41(6) . . ? O3 S1 O1 109.55(6) . . ? O2 S1 O1 109.03(6) . . ? O3 S1 C11 109.06(6) . . ? O2 S1 C11 110.33(6) . . ? O1 S1 C11 100.06(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 O1 -63.10(13) . . . . ? C7 C1 C2 O1 177.91(10) . . . . ? C6 C1 C2 C3 55.94(14) . . . . ? C7 C1 C2 C3 -63.05(13) . . . . ? O1 C2 C3 C4 62.06(13) . . . . ? C1 C2 C3 C4 -56.07(14) . . . . ? O1 C2 C3 C9 -178.64(10) . . . . ? C1 C2 C3 C9 63.24(13) . . . . ? C2 C3 C4 C5 58.49(14) . . . . ? C9 C3 C4 C5 -58.92(15) . . . . ? C3 C4 C5 C6 -60.74(14) . . . . ? C3 C4 C5 C10 59.27(15) . . . . ? C4 C5 C6 C1 60.35(14) . . . . ? C10 C5 C6 C1 -59.67(14) . . . . ? C2 C1 C6 C5 -58.16(14) . . . . ? C7 C1 C6 C5 59.46(14) . . . . ? C2 C1 C7 C8 60.15(15) . . . . ? C6 C1 C7 C8 -59.70(15) . . . . ? C1 C7 C8 C10 60.10(15) . . . . ? C1 C7 C8 C9 -60.00(15) . . . . ? C10 C8 C9 C3 -59.45(15) . . . . ? C7 C8 C9 C3 60.39(15) . . . . ? C2 C3 C9 C8 -60.63(14) . . . . ? C4 C3 C9 C8 58.94(15) . . . . ? C7 C8 C10 C5 -59.96(15) . . . . ? C9 C8 C10 C5 59.77(15) . . . . ? C6 C5 C10 C8 59.85(15) . . . . ? C4 C5 C10 C8 -59.61(15) . . . . ? C16 C11 C12 C13 1.30(19) . . . . ? S1 C11 C12 C13 -175.49(10) . . . . ? C11 C12 C13 C14 0.2(2) . . . . ? C12 C13 C14 C15 -1.64(19) . . . . ? C12 C13 C14 C17 178.18(12) . . . . ? C13 C14 C15 C16 1.57(19) . . . . ? C17 C14 C15 C16 -178.25(12) . . . . ? C14 C15 C16 C11 -0.10(19) . . . . ? C12 C11 C16 C15 -1.37(19) . . . . ? S1 C11 C16 C15 175.44(10) . . . . ? C1 C2 O1 S1 -135.49(9) . . . . ? C3 C2 O1 S1 103.86(10) . . . . ? C2 O1 S1 O3 96.46(10) . . . . ? C2 O1 S1 O2 -33.28(11) . . . . ? C2 O1 S1 C11 -149.02(9) . . . . ? C12 C11 S1 O3 -7.53(12) . . . . ? C16 C11 S1 O3 175.61(10) . . . . ? C12 C11 S1 O2 122.82(10) . . . . ? C16 C11 S1 O2 -54.05(11) . . . . ? C12 C11 S1 O1 -122.42(10) . . . . ? C16 C11 S1 O1 60.71(11) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.385 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.068