# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Dr Brian P Roberts' _publ_contact_author_address ; Department of Chemistry University College London Christopher Ingold Laboratories 20 Gordon Street London WC1H OAJ UNITED KINGDOM ; _publ_contact_author_email B.P.ROBERTS@UCL.AC.UK _publ_section_title ; Carbon-carbon formation by radical addition-fragmentation reactions of O-alkylated enols ; loop_ _publ_author_name 'Brian P. Roberts' 'Sarah A. Barnett' 'Yudong Cai' 'Derek A. Tocher' data_str0163_Structure_25 _database_code_depnum_ccdc_archive 'CCDC 238608' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H24 O3' _chemical_formula_weight 264.35 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' 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 P2(1)/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 12.9963(15) _cell_length_b 15.2812(17) _cell_length_c 15.4858(17) _cell_angle_alpha 90.00 _cell_angle_beta 113.494(2) _cell_angle_gamma 90.00 _cell_volume 2820.5(5) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9608 _exptl_absorpt_correction_T_max 0.9687 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22903 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 28.32 _reflns_number_total 6578 _reflns_number_gt 5697 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.1035P)^2^+0.8029P] 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 6578 _refine_ls_number_parameters 353 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1661 _refine_ls_wR_factor_gt 0.1588 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 1.05418(10) 0.61096(8) 0.05030(9) 0.0437(3) Uani 1 1 d . . . O2 O 0.89113(10) 0.64274(7) 0.05697(9) 0.0411(3) Uani 1 1 d . . . O3 O 0.71127(11) 0.58966(8) 0.01070(9) 0.0478(3) Uani 1 1 d . . . O4 O -0.01991(10) 0.98991(8) 0.11596(9) 0.0473(3) Uani 1 1 d . . . O5 O 0.15329(8) 0.93811(6) 0.16005(6) 0.0294(2) Uani 1 1 d . . . O6 O 0.30666(8) 0.90174(6) 0.12729(7) 0.0287(2) Uani 1 1 d . . . C1 C 0.98221(12) 0.59250(9) 0.07759(10) 0.0318(3) Uani 1 1 d . . . C2 C 0.97905(14) 0.51667(10) 0.13737(12) 0.0394(3) Uani 1 1 d . . . H2A H 1.0394 0.5217 0.2012 0.047 Uiso 1 1 calc R . . H2B H 0.9888 0.4609 0.1089 0.047 Uiso 1 1 calc R . . C3 C 0.86596(18) 0.52008(11) 0.14178(16) 0.0533(5) Uani 1 1 d . . . H3A H 0.8738 0.5218 0.2080 0.064 Uiso 1 1 calc R . . H3B H 0.8210 0.4680 0.1108 0.064 Uiso 1 1 calc R . . C4 C 0.80917(13) 0.60415(9) 0.08980(11) 0.0353(3) Uani 1 1 d . . . C5 C 0.7138(3) 0.52865(16) -0.05917(19) 0.0794(8) Uani 1 1 d . . . C6A C 0.5963(3) 0.4731(3) -0.0866(3) 0.0449(8) Uani 0.50 1 d P . . C6B C 0.6160(4) 0.5124(4) -0.1235(4) 0.0747(17) Uani 0.50 1 d P . . C7 C 0.77978(10) 0.67248(9) 0.14911(9) 0.0268(3) Uani 1 1 d . . . C8 C 0.88252(11) 0.69676(12) 0.23788(10) 0.0397(4) Uani 1 1 d . . . H8A H 0.9416 0.7213 0.2198 0.048 Uiso 1 1 calc R . . H8B H 0.9129 0.6436 0.2762 0.048 Uiso 1 1 calc R . . C9 C 0.73389(12) 0.75617(9) 0.09144(9) 0.0316(3) Uani 1 1 d . . . H9A H 0.7916 0.7814 0.0721 0.038 Uiso 1 1 calc R . . H9B H 0.6672 0.7417 0.0338 0.038 Uiso 1 1 calc R . . C10 C 0.68901(12) 0.63508(10) 0.17925(11) 0.0330(3) Uani 1 1 d . . . H10A H 0.6218 0.6191 0.1227 0.040 Uiso 1 1 calc R . . H10B H 0.7175 0.5815 0.2172 0.040 Uiso 1 1 calc R . . C11 C 0.85055(13) 0.76411(13) 0.29616(11) 0.0457(4) Uani 1 1 d . . . H11 H 0.9185 0.7792 0.3537 0.055 Uiso 1 1 calc R . . C12 C 0.80590(17) 0.84638(12) 0.23784(13) 0.0510(5) Uani 1 1 d . . . H12A H 0.8643 0.8717 0.2194 0.061 Uiso 1 1 calc R . . H12B H 0.7862 0.8905 0.2756 0.061 Uiso 1 1 calc R . . C13 C 0.70191(15) 0.82318(10) 0.14977(11) 0.0400(3) Uani 1 1 d . . . H13 H 0.6723 0.8772 0.1114 0.048 Uiso 1 1 calc R . . C14 C 0.61157(13) 0.78467(11) 0.17838(11) 0.0395(3) Uani 1 1 d . . . H14A H 0.5897 0.8282 0.2153 0.047 Uiso 1 1 calc R . . H14B H 0.5442 0.7698 0.1214 0.047 Uiso 1 1 calc R . . C15 C 0.65712(12) 0.70271(10) 0.23730(10) 0.0323(3) Uani 1 1 d . . . H15 H 0.5981 0.6776 0.2561 0.039 Uiso 1 1 calc R . . C16 C 0.76030(13) 0.72594(12) 0.32559(10) 0.0396(3) Uani 1 1 d . . . H16A H 0.7894 0.6729 0.3645 0.048 Uiso 1 1 calc R . . H16B H 0.7399 0.7693 0.3636 0.048 Uiso 1 1 calc R . . C17 C 0.04226(12) 0.93599(9) 0.10654(10) 0.0318(3) Uani 1 1 d . . . C18 C 0.01400(12) 0.86014(10) 0.03967(10) 0.0336(3) Uani 1 1 d . . . H18A H -0.0320 0.8795 -0.0254 0.040 Uiso 1 1 calc R . . H18B H -0.0279 0.8148 0.0580 0.040 Uiso 1 1 calc R . . C19 C 0.12627(11) 0.82529(9) 0.04714(9) 0.0278(3) Uani 1 1 d . . . H19A H 0.1410 0.8428 -0.0084 0.033 Uiso 1 1 calc R . . H19B H 0.1281 0.7606 0.0514 0.033 Uiso 1 1 calc R . . C20 C 0.21397(10) 0.86600(8) 0.13769(8) 0.0235(2) Uani 1 1 d . . . C21 C 0.28978(15) 0.97198(11) 0.06180(12) 0.0410(4) Uani 1 1 d . . . H21A H 0.2522 1.0219 0.0779 0.049 Uiso 1 1 calc R . . H21B H 0.2428 0.9525 -0.0030 0.049 Uiso 1 1 calc R . . C22 C 0.40327(19) 0.99786(17) 0.06915(15) 0.0738(8) Uani 1 1 d . . . H22A H 0.4496 1.0148 0.1342 0.111 Uiso 1 1 calc R . . H22B H 0.3967 1.0474 0.0271 0.111 Uiso 1 1 calc R . . H22C H 0.4383 0.9484 0.0510 0.111 Uiso 1 1 calc R . . C23 C 0.26098(10) 0.80537(8) 0.22408(8) 0.0220(2) Uani 1 1 d . . . C24 C 0.34033(11) 0.85678(9) 0.31080(9) 0.0264(3) Uani 1 1 d . . . H24A H 0.4028 0.8817 0.2976 0.032 Uiso 1 1 calc R . . H24B H 0.2989 0.9058 0.3240 0.032 Uiso 1 1 calc R . . C25 C 0.32858(11) 0.73042(9) 0.20488(9) 0.0269(3) Uani 1 1 d . . . H25A H 0.2792 0.6961 0.1497 0.032 Uiso 1 1 calc R . . H25B H 0.3904 0.7551 0.1905 0.032 Uiso 1 1 calc R . . C26 C 0.16613(10) 0.76574(9) 0.24673(9) 0.0266(3) Uani 1 1 d . . . H26A H 0.1146 0.7325 0.1916 0.032 Uiso 1 1 calc R . . H26B H 0.1228 0.8132 0.2601 0.032 Uiso 1 1 calc R . . C27 C 0.38740(11) 0.79675(9) 0.39687(9) 0.0300(3) Uani 1 1 d . . . H27 H 0.4379 0.8312 0.4526 0.036 Uiso 1 1 calc R . . C28 C 0.45410(12) 0.72282(10) 0.37694(10) 0.0343(3) Uani 1 1 d . . . H28A H 0.4855 0.6839 0.4325 0.041 Uiso 1 1 calc R . . H28B H 0.5172 0.7475 0.3644 0.041 Uiso 1 1 calc R . . C29 C 0.37703(12) 0.67043(9) 0.29148(9) 0.0323(3) Uani 1 1 d . . . H29 H 0.4210 0.6223 0.2784 0.039 Uiso 1 1 calc R . . C30 C 0.28106(13) 0.63099(10) 0.31153(10) 0.0372(3) Uani 1 1 d . . . H30A H 0.3115 0.5910 0.3662 0.045 Uiso 1 1 calc R . . H30B H 0.2313 0.5968 0.2564 0.045 Uiso 1 1 calc R . . C31 C 0.21407(12) 0.70449(10) 0.33244(9) 0.0326(3) Uani 1 1 d . . . H31 H 0.1512 0.6788 0.3459 0.039 Uiso 1 1 calc R . . C32 C 0.29137(12) 0.75739(11) 0.41799(9) 0.0344(3) Uani 1 1 d . . . H32A H 0.2482 0.8047 0.4318 0.041 Uiso 1 1 calc R . . H32B H 0.3223 0.7188 0.4739 0.041 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 0.0414(6) 0.0438(6) 0.0584(7) -0.0111(5) 0.0331(5) -0.0097(5) O2 0.0460(6) 0.0357(5) 0.0584(7) 0.0149(5) 0.0388(6) 0.0074(5) O3 0.0516(7) 0.0531(7) 0.0475(7) -0.0220(5) 0.0290(6) -0.0114(5) O4 0.0406(6) 0.0522(7) 0.0464(6) 0.0006(5) 0.0145(5) 0.0190(5) O5 0.0299(5) 0.0300(5) 0.0262(4) -0.0042(4) 0.0092(4) 0.0049(4) O6 0.0287(5) 0.0310(5) 0.0280(5) 0.0040(4) 0.0130(4) -0.0041(4) C1 0.0330(7) 0.0318(6) 0.0346(7) -0.0072(5) 0.0177(6) -0.0043(5) C2 0.0403(8) 0.0372(7) 0.0420(8) 0.0050(6) 0.0176(6) 0.0041(6) C3 0.0740(12) 0.0334(8) 0.0787(13) 0.0192(8) 0.0579(11) 0.0132(8) C4 0.0393(7) 0.0324(7) 0.0463(8) 0.0058(6) 0.0299(7) 0.0000(6) C5 0.134(2) 0.0584(12) 0.0800(16) -0.0346(12) 0.0794(17) -0.0283(14) C6A 0.0449(19) 0.0402(18) 0.045(2) -0.0082(15) 0.0134(15) -0.0064(15) C6B 0.044(2) 0.088(4) 0.071(3) -0.055(3) 0.001(2) 0.004(2) C7 0.0237(6) 0.0308(6) 0.0276(6) 0.0041(5) 0.0121(5) -0.0011(5) C8 0.0214(6) 0.0643(10) 0.0309(7) 0.0094(7) 0.0078(5) -0.0008(6) C9 0.0354(7) 0.0344(7) 0.0259(6) 0.0055(5) 0.0130(5) 0.0040(5) C10 0.0310(7) 0.0355(7) 0.0399(7) -0.0025(6) 0.0219(6) -0.0063(5) C11 0.0332(7) 0.0720(11) 0.0266(7) -0.0078(7) 0.0063(6) -0.0180(8) C12 0.0686(12) 0.0455(9) 0.0488(10) -0.0174(7) 0.0339(9) -0.0250(8) C13 0.0555(9) 0.0326(7) 0.0368(8) 0.0070(6) 0.0236(7) 0.0087(7) C14 0.0374(7) 0.0478(8) 0.0335(7) 0.0002(6) 0.0143(6) 0.0118(6) C15 0.0288(6) 0.0402(7) 0.0313(7) -0.0014(6) 0.0156(5) -0.0027(5) C16 0.0370(8) 0.0563(9) 0.0251(6) 0.0017(6) 0.0120(6) -0.0024(7) C17 0.0297(6) 0.0373(7) 0.0274(6) 0.0046(5) 0.0102(5) 0.0054(5) C18 0.0279(6) 0.0385(7) 0.0284(6) -0.0001(5) 0.0047(5) 0.0003(5) C19 0.0308(6) 0.0318(6) 0.0199(6) -0.0028(5) 0.0090(5) -0.0033(5) C20 0.0243(6) 0.0251(6) 0.0221(5) -0.0024(4) 0.0103(4) 0.0001(4) C21 0.0512(9) 0.0365(7) 0.0404(8) 0.0122(6) 0.0236(7) -0.0002(7) C22 0.0675(13) 0.0882(16) 0.0494(11) 0.0252(10) 0.0061(9) -0.0460(12) C23 0.0213(5) 0.0261(5) 0.0192(5) -0.0020(4) 0.0089(4) -0.0009(4) C24 0.0254(6) 0.0303(6) 0.0222(6) -0.0044(5) 0.0081(5) -0.0029(5) C25 0.0277(6) 0.0300(6) 0.0235(6) -0.0015(5) 0.0107(5) 0.0037(5) C26 0.0232(6) 0.0352(6) 0.0224(6) -0.0003(5) 0.0100(5) -0.0031(5) C27 0.0283(6) 0.0382(7) 0.0200(6) -0.0034(5) 0.0061(5) -0.0018(5) C28 0.0288(6) 0.0422(8) 0.0268(6) 0.0016(6) 0.0055(5) 0.0049(6) C29 0.0343(7) 0.0326(7) 0.0265(6) 0.0007(5) 0.0084(5) 0.0069(5) C30 0.0448(8) 0.0330(7) 0.0282(7) 0.0045(5) 0.0086(6) -0.0043(6) C31 0.0320(7) 0.0412(7) 0.0250(6) 0.0047(5) 0.0118(5) -0.0061(6) C32 0.0363(7) 0.0464(8) 0.0211(6) 0.0009(5) 0.0120(5) -0.0012(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 O1 C1 1.2034(17) . ? O2 C1 1.3382(18) . ? O2 C4 1.4739(16) . ? O3 C4 1.388(2) . ? O3 C5 1.438(2) . ? O4 C17 1.2029(18) . ? O5 C17 1.3478(17) . ? O5 C20 1.4743(14) . ? O6 C20 1.3892(15) . ? O6 C21 1.4323(17) . ? C1 C2 1.494(2) . ? C2 C3 1.499(2) . ? C3 C4 1.539(2) . ? C4 C7 1.5360(19) . ? C5 C6B 1.289(5) . ? C5 C6A 1.648(5) . ? C6A C6B 0.933(7) . ? C7 C8 1.5319(19) . ? C7 C9 1.5376(18) . ? C7 C10 1.5411(17) . ? C8 C11 1.531(2) . ? C9 C13 1.529(2) . ? C10 C15 1.5314(19) . ? C11 C12 1.522(3) . ? C11 C16 1.533(2) . ? C12 C13 1.531(2) . ? C13 C14 1.528(2) . ? C14 C15 1.523(2) . ? C15 C16 1.527(2) . ? C17 C18 1.499(2) . ? C18 C19 1.5137(19) . ? C19 C20 1.5422(17) . ? C20 C23 1.5394(16) . ? C21 C22 1.487(3) . ? C23 C26 1.5343(16) . ? C23 C24 1.5426(16) . ? C23 C25 1.5429(17) . ? C24 C27 1.5304(18) . ? C25 C29 1.5369(18) . ? C26 C31 1.5384(18) . ? C27 C28 1.529(2) . ? C27 C32 1.5336(19) . ? C28 C29 1.5293(19) . ? C29 C30 1.524(2) . ? C30 C31 1.533(2) . ? C31 C32 1.5351(19) . ? 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 C1 O2 C4 112.36(11) . . ? C4 O3 C5 118.67(18) . . ? C17 O5 C20 112.30(10) . . ? C20 O6 C21 118.79(11) . . ? O1 C1 O2 121.28(14) . . ? O1 C1 C2 128.07(14) . . ? O2 C1 C2 110.65(12) . . ? C1 C2 C3 105.71(12) . . ? C2 C3 C4 106.24(12) . . ? O3 C4 O2 107.08(12) . . ? O3 C4 C7 106.10(11) . . ? O2 C4 C7 108.69(11) . . ? O3 C4 C3 114.09(15) . . ? O2 C4 C3 104.62(12) . . ? C7 C4 C3 115.87(13) . . ? C6B C5 O3 113.3(3) . . ? C6B C5 C6A 34.4(3) . . ? O3 C5 C6A 103.4(2) . . ? C6B C6A C5 51.2(4) . . ? C6A C6B C5 94.4(6) . . ? C8 C7 C4 111.45(12) . . ? C8 C7 C9 108.49(12) . . ? C4 C7 C9 110.46(11) . . ? C8 C7 C10 108.46(11) . . ? C4 C7 C10 109.38(11) . . ? C9 C7 C10 108.53(11) . . ? C7 C8 C11 110.33(12) . . ? C13 C9 C7 110.36(11) . . ? C15 C10 C7 110.28(11) . . ? C12 C11 C8 109.54(13) . . ? C12 C11 C16 109.57(15) . . ? C8 C11 C16 109.81(14) . . ? C11 C12 C13 109.26(13) . . ? C14 C13 C9 109.56(13) . . ? C14 C13 C12 109.78(13) . . ? C9 C13 C12 109.28(14) . . ? C15 C14 C13 109.28(12) . . ? C14 C15 C16 109.76(13) . . ? C14 C15 C10 109.56(12) . . ? C16 C15 C10 109.63(12) . . ? C15 C16 C11 108.97(11) . . ? O4 C17 O5 121.02(14) . . ? O4 C17 C18 128.45(14) . . ? O5 C17 C18 110.53(11) . . ? C17 C18 C19 104.83(11) . . ? C18 C19 C20 105.55(10) . . ? O6 C20 O5 107.65(10) . . ? O6 C20 C23 105.98(10) . . ? O5 C20 C23 108.05(9) . . ? O6 C20 C19 114.45(10) . . ? O5 C20 C19 104.15(9) . . ? C23 C20 C19 116.16(10) . . ? O6 C21 C22 106.13(14) . . ? C26 C23 C20 111.07(10) . . ? C26 C23 C24 108.74(9) . . ? C20 C23 C24 110.24(10) . . ? C26 C23 C25 108.80(10) . . ? C20 C23 C25 109.78(9) . . ? C24 C23 C25 108.14(10) . . ? C27 C24 C23 110.45(10) . . ? C29 C25 C23 109.95(10) . . ? C23 C26 C31 110.57(10) . . ? C28 C27 C24 109.22(10) . . ? C28 C27 C32 109.17(12) . . ? C24 C27 C32 110.13(11) . . ? C27 C28 C29 109.46(11) . . ? C30 C29 C28 109.73(11) . . ? C30 C29 C25 109.25(11) . . ? C28 C29 C25 110.00(12) . . ? C29 C30 C31 109.45(12) . . ? C30 C31 C32 109.68(12) . . ? C30 C31 C26 109.41(11) . . ? C32 C31 C26 108.96(11) . . ? C27 C32 C31 109.31(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 C4 O2 C1 O1 174.79(13) . . . . ? C4 O2 C1 C2 -6.26(17) . . . . ? O1 C1 C2 C3 -174.37(16) . . . . ? O2 C1 C2 C3 6.76(18) . . . . ? C1 C2 C3 C4 -4.58(19) . . . . ? C5 O3 C4 O2 63.27(18) . . . . ? C5 O3 C4 C7 179.23(14) . . . . ? C5 O3 C4 C3 -51.98(19) . . . . ? C1 O2 C4 O3 -118.35(14) . . . . ? C1 O2 C4 C7 127.43(13) . . . . ? C1 O2 C4 C3 3.08(18) . . . . ? C2 C3 C4 O3 117.93(16) . . . . ? C2 C3 C4 O2 1.24(19) . . . . ? C2 C3 C4 C7 -118.40(15) . . . . ? C4 O3 C5 C6B 172.1(4) . . . . ? C4 O3 C5 C6A 137.3(2) . . . . ? O3 C5 C6A C6B 111.9(5) . . . . ? O3 C5 C6B C6A -79.4(5) . . . . ? O3 C4 C7 C8 -178.18(11) . . . . ? O2 C4 C7 C8 -63.33(15) . . . . ? C3 C4 C7 C8 54.07(17) . . . . ? O3 C4 C7 C9 -57.50(14) . . . . ? O2 C4 C7 C9 57.36(15) . . . . ? C3 C4 C7 C9 174.76(13) . . . . ? O3 C4 C7 C10 61.89(14) . . . . ? O2 C4 C7 C10 176.75(11) . . . . ? C3 C4 C7 C10 -65.85(17) . . . . ? C4 C7 C8 C11 -179.36(12) . . . . ? C9 C7 C8 C11 58.81(15) . . . . ? C10 C7 C8 C11 -58.90(16) . . . . ? C8 C7 C9 C13 -59.01(15) . . . . ? C4 C7 C9 C13 178.56(12) . . . . ? C10 C7 C9 C13 58.65(15) . . . . ? C8 C7 C10 C15 59.10(15) . . . . ? C4 C7 C10 C15 -179.16(12) . . . . ? C9 C7 C10 C15 -58.58(15) . . . . ? C7 C8 C11 C12 -60.25(16) . . . . ? C7 C8 C11 C16 60.12(16) . . . . ? C8 C11 C12 C13 60.32(17) . . . . ? C16 C11 C12 C13 -60.20(17) . . . . ? C7 C9 C13 C14 -60.12(16) . . . . ? C7 C9 C13 C12 60.19(16) . . . . ? C11 C12 C13 C14 59.83(17) . . . . ? C11 C12 C13 C9 -60.34(16) . . . . ? C9 C13 C14 C15 60.38(16) . . . . ? C12 C13 C14 C15 -59.62(17) . . . . ? C13 C14 C15 C16 60.06(15) . . . . ? C13 C14 C15 C10 -60.36(15) . . . . ? C7 C10 C15 C14 60.10(15) . . . . ? C7 C10 C15 C16 -60.40(15) . . . . ? C14 C15 C16 C11 -60.36(17) . . . . ? C10 C15 C16 C11 60.01(17) . . . . ? C12 C11 C16 C15 60.46(17) . . . . ? C8 C11 C16 C15 -59.89(17) . . . . ? C20 O5 C17 O4 179.60(13) . . . . ? C20 O5 C17 C18 -0.11(15) . . . . ? O4 C17 C18 C19 170.27(15) . . . . ? O5 C17 C18 C19 -10.05(15) . . . . ? C17 C18 C19 C20 15.52(14) . . . . ? C21 O6 C20 O5 -54.49(14) . . . . ? C21 O6 C20 C23 -169.92(11) . . . . ? C21 O6 C20 C19 60.74(15) . . . . ? C17 O5 C20 O6 131.87(11) . . . . ? C17 O5 C20 C23 -114.09(11) . . . . ? C17 O5 C20 C19 9.99(13) . . . . ? C18 C19 C20 O6 -132.80(11) . . . . ? C18 C19 C20 O5 -15.54(13) . . . . ? C18 C19 C20 C23 103.13(12) . . . . ? C20 O6 C21 C22 177.98(15) . . . . ? O6 C20 C23 C26 176.61(9) . . . . ? O5 C20 C23 C26 61.47(12) . . . . ? C19 C20 C23 C26 -55.05(13) . . . . ? O6 C20 C23 C24 56.02(12) . . . . ? O5 C20 C23 C24 -59.13(12) . . . . ? C19 C20 C23 C24 -175.65(10) . . . . ? O6 C20 C23 C25 -63.02(12) . . . . ? O5 C20 C23 C25 -178.17(9) . . . . ? C19 C20 C23 C25 65.32(13) . . . . ? C26 C23 C24 C27 58.08(13) . . . . ? C20 C23 C24 C27 -179.94(10) . . . . ? C25 C23 C24 C27 -59.91(13) . . . . ? C26 C23 C25 C29 -59.03(13) . . . . ? C20 C23 C25 C29 179.23(10) . . . . ? C24 C23 C25 C29 58.91(13) . . . . ? C20 C23 C26 C31 179.35(10) . . . . ? C24 C23 C26 C31 -59.17(13) . . . . ? C25 C23 C26 C31 58.40(13) . . . . ? C23 C24 C27 C28 60.85(14) . . . . ? C23 C24 C27 C32 -59.03(14) . . . . ? C24 C27 C28 C29 -59.93(15) . . . . ? C32 C27 C28 C29 60.53(14) . . . . ? C27 C28 C29 C30 -60.49(15) . . . . ? C27 C28 C29 C25 59.73(15) . . . . ? C23 C25 C29 C30 60.78(14) . . . . ? C23 C25 C29 C28 -59.73(14) . . . . ? C28 C29 C30 C31 59.72(14) . . . . ? C25 C29 C30 C31 -60.95(14) . . . . ? C29 C30 C31 C32 -59.42(14) . . . . ? C29 C30 C31 C26 60.04(14) . . . . ? C23 C26 C31 C30 -59.24(14) . . . . ? C23 C26 C31 C32 60.67(14) . . . . ? C28 C27 C32 C31 -60.17(14) . . . . ? C24 C27 C32 C31 59.73(15) . . . . ? C30 C31 C32 C27 59.72(15) . . . . ? C26 C31 C32 C27 -60.02(15) . . . . ? _diffrn_measured_fraction_theta_max 0.937 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.475 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.057 data_str0196_Structure_30b _database_code_depnum_ccdc_archive 'CCDC 238609' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H27 N O4' _chemical_formula_weight 333.42 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 P2(1)/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 6.7197(6) _cell_length_b 20.8230(17) _cell_length_c 12.2379(10) _cell_angle_alpha 90.00 _cell_angle_beta 98.890(2) _cell_angle_gamma 90.00 _cell_volume 1691.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9680 _exptl_absorpt_correction_T_max 0.9928 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14945 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4058 _reflns_number_gt 3215 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0691P)^2^+0.6810P] 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 4058 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0694 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1363 _refine_ls_wR_factor_gt 0.1255 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.992 _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 N1 N 0.0284(2) 0.79880(6) 0.41729(11) 0.0217(3) Uani 1 1 d . . . O1 O -0.16226(17) 0.83727(6) 0.54124(11) 0.0327(3) Uani 1 1 d . . . O2 O 0.2810(2) 0.75789(7) 0.33257(10) 0.0353(3) Uani 1 1 d . . . O3 O 0.49009(19) 0.64189(6) 0.65492(12) 0.0362(3) Uani 1 1 d . . . O4 O 0.20270(17) 0.67635(5) 0.55571(10) 0.0243(3) Uani 1 1 d . . . C1 C 0.0005(2) 0.82197(7) 0.52017(13) 0.0199(3) Uani 1 1 d . . . C2 C 0.2023(2) 0.82259(7) 0.59563(12) 0.0162(3) Uani 1 1 d . . . H2A H 0.1968 0.7900 0.6551 0.019 Uiso 1 1 calc R . . C3 C 0.3510(2) 0.79834(7) 0.52142(12) 0.0178(3) Uani 1 1 d . . . H3A H 0.4381 0.8355 0.5077 0.021 Uiso 1 1 calc R . . C4 C 0.2242(2) 0.78156(7) 0.41239(13) 0.0218(3) Uani 1 1 d . . . C5 C -0.1361(3) 0.78793(9) 0.32690(15) 0.0326(4) Uani 1 1 d . . . H5A H -0.2620 0.8040 0.3478 0.049 Uiso 1 1 calc R . . H5B H -0.1487 0.7418 0.3113 0.049 Uiso 1 1 calc R . . H5C H -0.1083 0.8106 0.2608 0.049 Uiso 1 1 calc R . . C6 C 0.4906(2) 0.74359(8) 0.56651(15) 0.0248(4) Uani 1 1 d . . . H6A H 0.5756 0.7329 0.5098 0.030 Uiso 1 1 calc R . . H6B H 0.5815 0.7599 0.6320 0.030 Uiso 1 1 calc R . . C7 C 0.3977(2) 0.68240(8) 0.59931(13) 0.0220(3) Uani 1 1 d . . . C8 C 0.1079(3) 0.61658(8) 0.58009(15) 0.0264(4) Uani 1 1 d . . . H8A H 0.1063 0.6127 0.6606 0.032 Uiso 1 1 calc R . . H8B H 0.1824 0.5796 0.5558 0.032 Uiso 1 1 calc R . . C9 C -0.1022(3) 0.61804(9) 0.51871(16) 0.0328(4) Uani 1 1 d . . . H9A H -0.1722 0.5784 0.5334 0.049 Uiso 1 1 calc R . . H9B H -0.0985 0.6216 0.4392 0.049 Uiso 1 1 calc R . . H9C H -0.1739 0.6550 0.5432 0.049 Uiso 1 1 calc R . . C10 C 0.2571(2) 0.88828(7) 0.65208(12) 0.0154(3) Uani 1 1 d . . . C11 C 0.4750(2) 0.88573(7) 0.71403(13) 0.0182(3) Uani 1 1 d . . . H11A H 0.4868 0.8512 0.7703 0.022 Uiso 1 1 calc R . . H11B H 0.5683 0.8758 0.6612 0.022 Uiso 1 1 calc R . . C12 C 0.1174(2) 0.90326(7) 0.73762(13) 0.0197(3) Uani 1 1 d . . . H12A H -0.0240 0.9052 0.7002 0.024 Uiso 1 1 calc R . . H12B H 0.1280 0.8686 0.7936 0.024 Uiso 1 1 calc R . . C13 C 0.2390(2) 0.94305(7) 0.56686(12) 0.0187(3) Uani 1 1 d . . . H13A H 0.3278 0.9341 0.5112 0.022 Uiso 1 1 calc R . . H13B H 0.0986 0.9456 0.5280 0.022 Uiso 1 1 calc R . . C14 C 0.5329(2) 0.95017(8) 0.77048(13) 0.0210(3) Uani 1 1 d . . . H14A H 0.6751 0.9479 0.8093 0.025 Uiso 1 1 calc R . . C15 C 0.5156(2) 1.00319(8) 0.68325(14) 0.0234(4) Uani 1 1 d . . . H15A H 0.5559 1.0448 0.7190 0.028 Uiso 1 1 calc R . . H15B H 0.6070 0.9939 0.6291 0.028 Uiso 1 1 calc R . . C16 C 0.2985(2) 1.00717(7) 0.62401(13) 0.0209(3) Uani 1 1 d . . . H16A H 0.2869 1.0422 0.5676 0.025 Uiso 1 1 calc R . . C17 C 0.1582(3) 1.02137(8) 0.70835(14) 0.0240(4) Uani 1 1 d . . . H17A H 0.0174 1.0244 0.6703 0.029 Uiso 1 1 calc R . . H17B H 0.1952 1.0630 0.7452 0.029 Uiso 1 1 calc R . . C18 C 0.1762(2) 0.96758(8) 0.79466(13) 0.0222(3) Uani 1 1 d . . . H18A H 0.0838 0.9768 0.8494 0.027 Uiso 1 1 calc R . . C19 C 0.3930(3) 0.96466(8) 0.85469(13) 0.0244(4) Uani 1 1 d . . . H19A H 0.4057 0.9307 0.9119 0.029 Uiso 1 1 calc R . . H19B H 0.4304 1.0062 0.8916 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 N1 0.0245(7) 0.0200(6) 0.0181(7) -0.0004(5) -0.0042(5) -0.0005(5) O1 0.0175(6) 0.0387(7) 0.0420(8) -0.0117(6) 0.0051(5) -0.0035(5) O2 0.0409(8) 0.0401(8) 0.0256(7) -0.0139(6) 0.0074(6) -0.0014(6) O3 0.0302(7) 0.0284(7) 0.0466(8) 0.0146(6) -0.0044(6) 0.0024(5) O4 0.0214(6) 0.0170(5) 0.0331(7) 0.0038(5) -0.0001(5) -0.0019(4) C1 0.0213(8) 0.0155(7) 0.0225(8) -0.0004(6) 0.0018(6) -0.0037(6) C2 0.0175(7) 0.0147(7) 0.0165(7) 0.0011(6) 0.0025(6) -0.0013(6) C3 0.0193(7) 0.0145(7) 0.0194(7) -0.0013(6) 0.0025(6) -0.0001(6) C4 0.0285(9) 0.0165(7) 0.0202(8) -0.0030(6) 0.0027(7) -0.0020(6) C5 0.0336(10) 0.0332(10) 0.0260(9) 0.0005(8) -0.0109(8) -0.0032(8) C6 0.0198(8) 0.0189(8) 0.0343(9) -0.0005(7) 0.0001(7) 0.0008(6) C7 0.0218(8) 0.0201(8) 0.0237(8) -0.0011(6) 0.0019(6) 0.0027(6) C8 0.0277(9) 0.0190(8) 0.0336(9) 0.0043(7) 0.0084(7) -0.0034(7) C9 0.0278(9) 0.0336(10) 0.0371(10) 0.0016(8) 0.0049(8) -0.0079(8) C10 0.0170(7) 0.0146(7) 0.0144(7) -0.0002(5) 0.0015(6) -0.0008(5) C11 0.0182(7) 0.0182(7) 0.0174(7) -0.0013(6) -0.0001(6) 0.0004(6) C12 0.0210(7) 0.0199(7) 0.0189(7) -0.0021(6) 0.0050(6) -0.0016(6) C13 0.0223(8) 0.0167(7) 0.0167(7) 0.0009(6) 0.0017(6) 0.0001(6) C14 0.0209(8) 0.0214(8) 0.0195(8) -0.0030(6) -0.0012(6) -0.0022(6) C15 0.0265(8) 0.0193(8) 0.0246(8) -0.0042(6) 0.0052(7) -0.0073(6) C16 0.0290(9) 0.0140(7) 0.0194(8) 0.0020(6) 0.0028(6) -0.0008(6) C17 0.0274(8) 0.0187(8) 0.0254(8) -0.0039(6) 0.0022(7) 0.0023(6) C18 0.0252(8) 0.0223(8) 0.0204(8) -0.0051(6) 0.0072(6) -0.0005(6) C19 0.0318(9) 0.0246(8) 0.0156(7) -0.0037(6) 0.0003(6) -0.0032(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 N1 C4 1.374(2) . ? N1 C1 1.388(2) . ? N1 C5 1.455(2) . ? O1 C1 1.205(2) . ? O2 C4 1.207(2) . ? O3 C7 1.196(2) . ? O4 C7 1.3422(19) . ? O4 C8 1.4500(19) . ? C1 C2 1.518(2) . ? C2 C3 1.536(2) . ? C2 C10 1.551(2) . ? C3 C4 1.509(2) . ? C3 C6 1.524(2) . ? C6 C7 1.501(2) . ? C8 C9 1.494(2) . ? C10 C13 1.537(2) . ? C10 C12 1.542(2) . ? C10 C11 1.542(2) . ? C11 C14 1.532(2) . ? C12 C18 1.534(2) . ? C13 C16 1.532(2) . ? C14 C15 1.528(2) . ? C14 C19 1.529(2) . ? C15 C16 1.528(2) . ? C16 C17 1.531(2) . ? C17 C18 1.531(2) . ? C18 C19 1.528(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 C4 N1 C1 113.24(13) . . ? C4 N1 C5 123.10(14) . . ? C1 N1 C5 123.41(15) . . ? C7 O4 C8 115.59(12) . . ? O1 C1 N1 122.69(15) . . ? O1 C1 C2 128.51(15) . . ? N1 C1 C2 108.79(13) . . ? C1 C2 C3 103.83(12) . . ? C1 C2 C10 114.01(12) . . ? C3 C2 C10 114.96(12) . . ? C4 C3 C6 112.24(13) . . ? C4 C3 C2 105.61(12) . . ? C6 C3 C2 116.88(13) . . ? O2 C4 N1 124.48(15) . . ? O2 C4 C3 127.19(15) . . ? N1 C4 C3 108.33(13) . . ? C7 C6 C3 118.28(14) . . ? O3 C7 O4 123.31(15) . . ? O3 C7 C6 123.40(15) . . ? O4 C7 C6 113.22(13) . . ? O4 C8 C9 106.88(14) . . ? C13 C10 C12 108.54(12) . . ? C13 C10 C11 109.18(12) . . ? C12 C10 C11 107.73(12) . . ? C13 C10 C2 111.32(12) . . ? C12 C10 C2 110.69(12) . . ? C11 C10 C2 109.31(12) . . ? C14 C11 C10 110.34(12) . . ? C18 C12 C10 110.16(12) . . ? C16 C13 C10 110.44(12) . . ? C15 C14 C19 109.89(13) . . ? C15 C14 C11 109.35(12) . . ? C19 C14 C11 109.67(13) . . ? C16 C15 C14 109.56(13) . . ? C15 C16 C17 109.46(13) . . ? C15 C16 C13 109.42(13) . . ? C17 C16 C13 109.37(13) . . ? C16 C17 C18 109.43(13) . . ? C19 C18 C17 109.17(13) . . ? C19 C18 C12 110.08(13) . . ? C17 C18 C12 109.73(13) . . ? C18 C19 C14 108.90(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 C4 N1 C1 O1 -177.30(15) . . . . ? C5 N1 C1 O1 -2.9(2) . . . . ? C4 N1 C1 C2 1.58(17) . . . . ? C5 N1 C1 C2 175.95(14) . . . . ? O1 C1 C2 C3 -179.76(16) . . . . ? N1 C1 C2 C3 1.45(15) . . . . ? O1 C1 C2 C10 -53.9(2) . . . . ? N1 C1 C2 C10 127.28(13) . . . . ? C1 C2 C3 C4 -3.61(15) . . . . ? C10 C2 C3 C4 -128.83(13) . . . . ? C1 C2 C3 C6 -129.21(13) . . . . ? C10 C2 C3 C6 105.57(15) . . . . ? C1 N1 C4 O2 176.92(16) . . . . ? C5 N1 C4 O2 2.5(3) . . . . ? C1 N1 C4 C3 -4.01(18) . . . . ? C5 N1 C4 C3 -178.40(14) . . . . ? C6 C3 C4 O2 -47.9(2) . . . . ? C2 C3 C4 O2 -176.28(16) . . . . ? C6 C3 C4 N1 133.10(14) . . . . ? C2 C3 C4 N1 4.68(16) . . . . ? C4 C3 C6 C7 -65.3(2) . . . . ? C2 C3 C6 C7 56.9(2) . . . . ? C8 O4 C7 O3 -0.1(2) . . . . ? C8 O4 C7 C6 176.98(14) . . . . ? C3 C6 C7 O3 -164.70(16) . . . . ? C3 C6 C7 O4 18.2(2) . . . . ? C7 O4 C8 C9 -176.57(14) . . . . ? C1 C2 C10 C13 -52.01(17) . . . . ? C3 C2 C10 C13 67.72(16) . . . . ? C1 C2 C10 C12 68.80(16) . . . . ? C3 C2 C10 C12 -171.47(12) . . . . ? C1 C2 C10 C11 -172.70(12) . . . . ? C3 C2 C10 C11 -52.97(16) . . . . ? C13 C10 C11 C14 57.94(16) . . . . ? C12 C10 C11 C14 -59.74(16) . . . . ? C2 C10 C11 C14 179.93(12) . . . . ? C13 C10 C12 C18 -58.82(16) . . . . ? C11 C10 C12 C18 59.28(16) . . . . ? C2 C10 C12 C18 178.74(12) . . . . ? C12 C10 C13 C16 59.28(16) . . . . ? C11 C10 C13 C16 -57.89(16) . . . . ? C2 C10 C13 C16 -178.66(12) . . . . ? C10 C11 C14 C15 -59.61(16) . . . . ? C10 C11 C14 C19 60.95(16) . . . . ? C19 C14 C15 C16 -59.74(16) . . . . ? C11 C14 C15 C16 60.69(16) . . . . ? C14 C15 C16 C17 59.21(16) . . . . ? C14 C15 C16 C13 -60.63(16) . . . . ? C10 C13 C16 C15 59.56(16) . . . . ? C10 C13 C16 C17 -60.33(16) . . . . ? C15 C16 C17 C18 -59.94(16) . . . . ? C13 C16 C17 C18 59.93(16) . . . . ? C16 C17 C18 C19 60.87(16) . . . . ? C16 C17 C18 C12 -59.86(17) . . . . ? C10 C12 C18 C19 -60.43(16) . . . . ? C10 C12 C18 C17 59.74(17) . . . . ? C17 C18 C19 C14 -60.80(16) . . . . ? C12 C18 C19 C14 59.70(17) . . . . ? C15 C14 C19 C18 60.44(16) . . . . ? C11 C14 C19 C18 -59.80(17) . . . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.366 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.050 data_str0246_Structure_36a _database_code_depnum_ccdc_archive 'CCDC 238610' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H29 N O4' _chemical_formula_weight 323.42 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 orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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' _cell_length_a 8.1750(15) _cell_length_b 10.6612(19) _cell_length_c 20.842(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1816.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'block cut from large crysral' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.37 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.183 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9615 _exptl_absorpt_correction_T_max 0.9701 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16073 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28.34 _reflns_number_total 4242 _reflns_number_gt 4055 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0795P)^2^+0.1475P] 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 0.035(4) _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 0.4(12) _refine_ls_number_reflns 4242 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1301 _refine_ls_wR_factor_gt 0.1281 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 O1 O 0.0185(2) 0.23813(12) 0.71736(7) 0.0653(4) Uani 1 1 d . . . O2 O -0.1407(2) 0.08143(15) 0.68661(7) 0.0652(4) Uani 1 1 d . . . O3 O 0.4035(2) 0.13880(16) 0.73069(8) 0.0686(4) Uani 1 1 d . . . O4 O 0.2280(2) 0.35181(12) 0.90534(6) 0.0653(4) Uani 1 1 d . . . N1 N 0.34306(18) 0.26461(14) 0.81647(7) 0.0453(3) Uani 1 1 d . . . C1 C 0.3542(3) -0.0530(3) 1.05272(11) 0.0708(6) Uani 1 1 d . . . H1A H 0.3294 -0.0882 1.0940 0.106 Uiso 1 1 calc R . . H1B H 0.4283 0.0161 1.0578 0.106 Uiso 1 1 calc R . . H1C H 0.4038 -0.1159 1.0261 0.106 Uiso 1 1 calc R . . C2 C 0.1965(2) -0.00689(17) 1.02121(8) 0.0455(4) Uani 1 1 d . . . H2A H 0.1498 0.0587 1.0486 0.055 Uiso 1 1 calc R . . C3 C 0.0705(2) -0.11026(16) 1.01463(8) 0.0458(4) Uani 1 1 d . . . H3A H 0.0459 -0.1440 1.0568 0.055 Uiso 1 1 calc R . . H3B H 0.1157 -0.1775 0.9888 0.055 Uiso 1 1 calc R . . C4 C -0.0860(2) -0.06357(16) 0.98385(8) 0.0433(4) Uani 1 1 d . . . H4A H -0.1363 -0.0019 1.0118 0.052 Uiso 1 1 calc R . . H4B H -0.1615 -0.1332 0.9794 0.052 Uiso 1 1 calc R . . C5 C -0.05704(17) -0.00429(14) 0.91746(7) 0.0349(3) Uani 1 1 d . . . H5A H -0.0118 -0.0700 0.8897 0.042 Uiso 1 1 calc R . . C6 C 0.07379(18) 0.09921(13) 0.92310(7) 0.0337(3) Uani 1 1 d . . . H6A H 0.0287 0.1642 0.9512 0.040 Uiso 1 1 calc R . . C7 C 0.2292(2) 0.05003(16) 0.95543(8) 0.0417(3) Uani 1 1 d . . . H7A H 0.2788 -0.0130 0.9281 0.050 Uiso 1 1 calc R . . H7B H 0.3065 0.1185 0.9600 0.050 Uiso 1 1 calc R . . C8 C -0.21898(19) 0.04002(17) 0.88647(8) 0.0440(4) Uani 1 1 d . . . H8A H -0.1911 0.0725 0.8438 0.053 Uiso 1 1 calc R . . C9 C -0.3007(3) 0.1474(2) 0.92290(12) 0.0636(5) Uani 1 1 d . . . H9A H -0.3998 0.1711 0.9013 0.095 Uiso 1 1 calc R . . H9B H -0.2278 0.2180 0.9245 0.095 Uiso 1 1 calc R . . H9C H -0.3258 0.1207 0.9658 0.095 Uiso 1 1 calc R . . C10 C -0.3376(3) -0.0681(2) 0.87617(12) 0.0662(6) Uani 1 1 d . . . H10A H -0.4362 -0.0371 0.8568 0.099 Uiso 1 1 calc R . . H10B H -0.3631 -0.1061 0.9167 0.099 Uiso 1 1 calc R . . H10C H -0.2884 -0.1294 0.8485 0.099 Uiso 1 1 calc R . . C11 C 0.11144(19) 0.16231(13) 0.85821(7) 0.0350(3) Uani 1 1 d . . . H11A H 0.0084 0.1960 0.8415 0.042 Uiso 1 1 calc R . . C12 C 0.1878(2) 0.08089(13) 0.80533(7) 0.0375(3) Uani 1 1 d . . . H12A H 0.2396 0.0088 0.8263 0.045 Uiso 1 1 calc R . . C13 C 0.0757(2) 0.03001(15) 0.75320(8) 0.0450(4) Uani 1 1 d . . . H13A H 0.1408 -0.0167 0.7225 0.054 Uiso 1 1 calc R . . H13B H -0.0015 -0.0279 0.7725 0.054 Uiso 1 1 calc R . . C14 C -0.0176(2) 0.12993(15) 0.71815(7) 0.0421(4) Uani 1 1 d . . . C15 C -0.2343(3) 0.1640(3) 0.64668(12) 0.0773(7) Uani 1 1 d . . . H15A H -0.3197 0.1174 0.6259 0.116 Uiso 1 1 calc R . . H15B H -0.1642 0.2007 0.6149 0.116 Uiso 1 1 calc R . . H15C H -0.2817 0.2290 0.6725 0.116 Uiso 1 1 calc R . . C16 C 0.3232(2) 0.16118(16) 0.77745(8) 0.0450(4) Uani 1 1 d . . . C17 C 0.2294(2) 0.27103(14) 0.86521(8) 0.0434(4) Uani 1 1 d . . . C18 C 0.4660(3) 0.3612(2) 0.80524(11) 0.0662(6) Uani 1 1 d . . . H18A H 0.5311 0.3387 0.7687 0.099 Uiso 1 1 calc R . . H18B H 0.5350 0.3685 0.8423 0.099 Uiso 1 1 calc R . . H18C H 0.4128 0.4400 0.7973 0.099 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 0.0898(11) 0.0350(6) 0.0712(9) 0.0027(6) -0.0308(8) -0.0028(7) O2 0.0732(9) 0.0662(8) 0.0561(8) 0.0101(7) -0.0201(7) -0.0250(8) O3 0.0678(9) 0.0689(9) 0.0693(9) -0.0024(8) 0.0325(8) 0.0026(8) O4 0.1051(12) 0.0431(6) 0.0475(7) -0.0075(6) 0.0029(8) -0.0179(8) N1 0.0467(7) 0.0417(7) 0.0475(8) 0.0081(6) -0.0008(6) -0.0071(6) C1 0.0680(13) 0.0837(16) 0.0607(12) 0.0208(11) -0.0252(10) -0.0068(12) C2 0.0531(9) 0.0489(9) 0.0345(7) 0.0057(6) -0.0033(7) 0.0032(8) C3 0.0540(9) 0.0420(8) 0.0414(7) 0.0105(6) 0.0046(7) 0.0044(7) C4 0.0417(7) 0.0435(8) 0.0449(8) 0.0087(7) 0.0072(7) -0.0036(7) C5 0.0330(7) 0.0362(7) 0.0355(7) 0.0009(5) 0.0030(6) 0.0016(6) C6 0.0381(7) 0.0326(6) 0.0303(6) 0.0010(5) 0.0042(6) 0.0012(6) C7 0.0380(7) 0.0480(8) 0.0390(7) 0.0077(6) -0.0018(6) -0.0027(7) C8 0.0360(7) 0.0531(9) 0.0427(8) 0.0025(7) -0.0016(6) 0.0009(7) C9 0.0512(10) 0.0678(12) 0.0719(12) -0.0049(10) -0.0061(10) 0.0236(10) C10 0.0488(9) 0.0726(13) 0.0771(14) -0.0061(11) -0.0133(9) -0.0107(10) C11 0.0412(7) 0.0329(7) 0.0310(6) 0.0020(5) 0.0000(6) 0.0022(6) C12 0.0468(8) 0.0297(6) 0.0361(7) 0.0027(5) 0.0041(6) 0.0045(6) C13 0.0669(11) 0.0295(7) 0.0385(7) -0.0044(5) 0.0066(7) -0.0041(7) C14 0.0581(10) 0.0385(7) 0.0296(7) -0.0043(5) 0.0035(7) -0.0048(7) C15 0.0717(14) 0.0982(17) 0.0620(12) 0.0136(12) -0.0222(11) -0.0111(14) C16 0.0457(8) 0.0440(8) 0.0453(8) 0.0053(7) 0.0059(7) 0.0054(7) C17 0.0597(10) 0.0333(7) 0.0370(7) 0.0052(6) -0.0025(7) -0.0035(7) C18 0.0656(12) 0.0671(12) 0.0660(12) 0.0148(10) 0.0000(10) -0.0273(11) _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 C14 1.191(2) . ? O2 C14 1.309(2) . ? O2 C15 1.433(3) . ? O3 C16 1.199(2) . ? O4 C17 1.200(2) . ? N1 C17 1.378(2) . ? N1 C16 1.380(2) . ? N1 C18 1.458(2) . ? C1 C2 1.528(3) . ? C2 C3 1.514(3) . ? C2 C7 1.523(2) . ? C3 C4 1.516(2) . ? C4 C5 1.539(2) . ? C5 C6 1.541(2) . ? C5 C8 1.547(2) . ? C6 C7 1.530(2) . ? C6 C11 1.5415(19) . ? C8 C10 1.522(3) . ? C8 C9 1.528(3) . ? C11 C17 1.515(2) . ? C11 C12 1.536(2) . ? C12 C16 1.515(2) . ? C12 C13 1.522(2) . ? C13 C14 1.500(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 C14 O2 C15 117.38(16) . . ? C17 N1 C16 113.24(14) . . ? C17 N1 C18 123.23(16) . . ? C16 N1 C18 123.44(16) . . ? C3 C2 C7 109.14(13) . . ? C3 C2 C1 112.22(16) . . ? C7 C2 C1 111.54(16) . . ? C2 C3 C4 111.92(13) . . ? C3 C4 C5 112.67(13) . . ? C4 C5 C6 109.40(12) . . ? C4 C5 C8 111.66(12) . . ? C6 C5 C8 114.02(12) . . ? C7 C6 C11 111.72(12) . . ? C7 C6 C5 111.36(12) . . ? C11 C6 C5 112.59(12) . . ? C2 C7 C6 112.79(14) . . ? C10 C8 C9 111.05(16) . . ? C10 C8 C5 111.90(15) . . ? C9 C8 C5 113.29(14) . . ? C17 C11 C12 104.04(13) . . ? C17 C11 C6 112.12(12) . . ? C12 C11 C6 117.65(12) . . ? C16 C12 C13 111.57(13) . . ? C16 C12 C11 104.65(12) . . ? C13 C12 C11 117.96(14) . . ? C14 C13 C12 113.63(13) . . ? O1 C14 O2 124.49(18) . . ? O1 C14 C13 124.68(17) . . ? O2 C14 C13 110.79(14) . . ? O3 C16 N1 124.99(17) . . ? O3 C16 C12 126.82(17) . . ? N1 C16 C12 108.17(14) . . ? O4 C17 N1 123.76(17) . . ? O4 C17 C11 127.56(17) . . ? N1 C17 C11 108.67(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 C7 C2 C3 C4 -56.30(19) . . . . ? C1 C2 C3 C4 179.53(16) . . . . ? C2 C3 C4 C5 57.02(19) . . . . ? C3 C4 C5 C6 -54.03(17) . . . . ? C3 C4 C5 C8 178.79(14) . . . . ? C4 C5 C6 C7 52.91(16) . . . . ? C8 C5 C6 C7 178.74(13) . . . . ? C4 C5 C6 C11 179.30(12) . . . . ? C8 C5 C6 C11 -54.88(16) . . . . ? C3 C2 C7 C6 56.42(19) . . . . ? C1 C2 C7 C6 -179.01(17) . . . . ? C11 C6 C7 C2 177.09(13) . . . . ? C5 C6 C7 C2 -56.05(17) . . . . ? C4 C5 C8 C10 -60.85(19) . . . . ? C6 C5 C8 C10 174.51(15) . . . . ? C4 C5 C8 C9 65.63(19) . . . . ? C6 C5 C8 C9 -59.00(19) . . . . ? C7 C6 C11 C17 -58.62(17) . . . . ? C5 C6 C11 C17 175.19(12) . . . . ? C7 C6 C11 C12 61.95(17) . . . . ? C5 C6 C11 C12 -64.24(17) . . . . ? C17 C11 C12 C16 -10.84(15) . . . . ? C6 C11 C12 C16 -135.54(13) . . . . ? C17 C11 C12 C13 -135.52(14) . . . . ? C6 C11 C12 C13 99.78(16) . . . . ? C16 C12 C13 C14 -64.67(19) . . . . ? C11 C12 C13 C14 56.51(19) . . . . ? C15 O2 C14 O1 2.4(3) . . . . ? C15 O2 C14 C13 -175.34(19) . . . . ? C12 C13 C14 O1 18.9(3) . . . . ? C12 C13 C14 O2 -163.37(15) . . . . ? C17 N1 C16 O3 176.99(18) . . . . ? C18 N1 C16 O3 0.2(3) . . . . ? C17 N1 C16 C12 -4.83(19) . . . . ? C18 N1 C16 C12 178.41(16) . . . . ? C13 C12 C16 O3 -43.3(2) . . . . ? C11 C12 C16 O3 -171.98(18) . . . . ? C13 C12 C16 N1 138.53(14) . . . . ? C11 C12 C16 N1 9.89(17) . . . . ? C16 N1 C17 O4 178.01(17) . . . . ? C18 N1 C17 O4 -5.2(3) . . . . ? C16 N1 C17 C11 -2.54(19) . . . . ? C18 N1 C17 C11 174.23(16) . . . . ? C12 C11 C17 O4 -172.02(18) . . . . ? C6 C11 C17 O4 -43.8(2) . . . . ? C12 C11 C17 N1 8.55(16) . . . . ? C6 C11 C17 N1 136.73(13) . . . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.202 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.039 data_str0255_Structure_37a _database_code_depnum_ccdc_archive 'CCDC 238611' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H27 N O4' _chemical_formula_weight 321.41 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' 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 orthorhombic _symmetry_space_group_name_H-M C222(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.2843(8) _cell_length_b 10.1695(9) _cell_length_c 41.757(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3517.9(6) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.214 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9588 _exptl_absorpt_correction_T_max 0.9975 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15592 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -54 _diffrn_reflns_limit_l_max 54 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28.26 _reflns_number_total 4212 _reflns_number_gt 3685 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.1174P)^2^+5.8052P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(2) _refine_ls_number_reflns 4212 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0976 _refine_ls_R_factor_gt 0.0878 _refine_ls_wR_factor_ref 0.2295 _refine_ls_wR_factor_gt 0.2216 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 0.4085(3) 0.2058(3) 0.20437(6) 0.0509(8) Uani 1 1 d . . . O2 O 0.1856(3) 0.2557(3) 0.23229(6) 0.0477(7) Uani 1 1 d . . . O3 O 0.5351(3) 0.5430(3) 0.18291(7) 0.0438(7) Uani 1 1 d . . . O4 O 0.6269(4) 0.1534(3) 0.13455(7) 0.0584(9) Uani 1 1 d . . . N1 N 0.6195(3) 0.3578(3) 0.15692(6) 0.0274(6) Uani 1 1 d . . . C1 C 0.2254(6) 0.1511(5) 0.25422(9) 0.0568(12) Uani 1 1 d . . . H1A H 0.1445 0.1475 0.2713 0.085 Uiso 1 1 calc R . . H1B H 0.3321 0.1674 0.2635 0.085 Uiso 1 1 calc R . . H1C H 0.2267 0.0671 0.2427 0.085 Uiso 1 1 calc R . . C2 C 0.2873(4) 0.2703(4) 0.20783(8) 0.0405(9) Uani 1 1 d . . . C3 C 0.2283(4) 0.3743(4) 0.18541(9) 0.0426(9) Uani 1 1 d . . . H3A H 0.2161 0.4577 0.1974 0.051 Uiso 1 1 calc R . . H3B H 0.1203 0.3488 0.1774 0.051 Uiso 1 1 calc R . . C4 C 0.3395(4) 0.3980(3) 0.15687(8) 0.0288(7) Uani 1 1 d . . . H4A H 0.2904 0.4682 0.1432 0.035 Uiso 1 1 calc R . . C5 C 0.5045(4) 0.4446(3) 0.16761(8) 0.0272(6) Uani 1 1 d . . . C6 C 0.7878(4) 0.3645(4) 0.16648(9) 0.0398(8) Uani 1 1 d . . . H6A H 0.8086 0.4489 0.1770 0.060 Uiso 1 1 calc R . . H6B H 0.8567 0.3566 0.1475 0.060 Uiso 1 1 calc R . . H6C H 0.8118 0.2926 0.1814 0.060 Uiso 1 1 calc R . . C7 C 0.5534(4) 0.2515(3) 0.14138(7) 0.0333(7) Uani 1 1 d . . . C8 C 0.3752(4) 0.2783(3) 0.13544(7) 0.0283(6) Uani 1 1 d . . . H8A H 0.3102 0.2014 0.1430 0.034 Uiso 1 1 calc R . . C9 C 0.3294(4) 0.3106(3) 0.10089(7) 0.0302(7) Uani 1 1 d . . . H9A H 0.3830 0.3952 0.0949 0.036 Uiso 1 1 calc R . . C10 C 0.1359(5) 0.3315(4) 0.09874(8) 0.0399(8) Uani 1 1 d . . . H10A H 0.0818 0.3049 0.1189 0.048 Uiso 1 1 calc R . . H10B H 0.1082 0.4240 0.0939 0.048 Uiso 1 1 calc R . . C11 C 0.0912(5) 0.2412(4) 0.07137(10) 0.0448(9) Uani 1 1 d . . . H11A H -0.0156 0.2614 0.0614 0.054 Uiso 1 1 calc R . . C12 C 0.1067(7) 0.0990(5) 0.08390(13) 0.0613(13) Uani 1 1 d . . . H12A H 0.0521 0.0362 0.0694 0.074 Uiso 1 1 calc R . . H12B H 0.0598 0.0905 0.1056 0.074 Uiso 1 1 calc R . . C13 C 0.2910(6) 0.0750(4) 0.08449(10) 0.0504(11) Uani 1 1 d . . . H13A H 0.3222 0.0052 0.0692 0.060 Uiso 1 1 calc R . . H13B H 0.3279 0.0500 0.1062 0.060 Uiso 1 1 calc R . . C14 C 0.3619(5) 0.2102(3) 0.07435(8) 0.0362(8) Uani 1 1 d . . . C15 C 0.5325(6) 0.2099(4) 0.06326(10) 0.0486(10) Uani 1 1 d . . . H15A H 0.6030 0.1820 0.0809 0.073 Uiso 1 1 calc R . . H15B H 0.5629 0.2986 0.0564 0.073 Uiso 1 1 calc R . . H15C H 0.5441 0.1488 0.0453 0.073 Uiso 1 1 calc R . . C16 C 0.2344(5) 0.2530(4) 0.04831(8) 0.0415(9) Uani 1 1 d . . . C17 C 0.2259(8) 0.1600(5) 0.01961(12) 0.0729(16) Uani 1 1 d . . . H17A H 0.1441 0.1917 0.0045 0.109 Uiso 1 1 calc R . . H17B H 0.1969 0.0716 0.0270 0.109 Uiso 1 1 calc R . . H17C H 0.3313 0.1572 0.0090 0.109 Uiso 1 1 calc R . . C18 C 0.2580(7) 0.3908(4) 0.03566(11) 0.0574(12) Uani 1 1 d . . . H18A H 0.1740 0.4105 0.0199 0.086 Uiso 1 1 calc R . . H18B H 0.3644 0.3976 0.0255 0.086 Uiso 1 1 calc R . . H18C H 0.2511 0.4536 0.0534 0.086 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 0.0337(14) 0.079(2) 0.0402(14) 0.0212(14) -0.0015(11) 0.0059(14) O2 0.0396(14) 0.0710(19) 0.0326(12) -0.0060(13) 0.0056(11) -0.0136(14) O3 0.0343(13) 0.0388(14) 0.0584(16) -0.0173(13) -0.0053(12) 0.0008(11) O4 0.070(2) 0.0450(16) 0.0601(18) -0.0176(14) -0.0297(16) 0.0398(15) N1 0.0207(12) 0.0346(14) 0.0270(12) 0.0002(11) -0.0034(10) 0.0035(11) C1 0.054(3) 0.088(3) 0.0281(17) 0.009(2) -0.0035(17) -0.028(3) C2 0.0226(15) 0.064(2) 0.0344(16) -0.0016(17) -0.0037(13) -0.0132(17) C3 0.0216(15) 0.060(2) 0.046(2) -0.0017(18) 0.0004(14) 0.0050(16) C4 0.0224(14) 0.0293(15) 0.0348(16) -0.0002(13) -0.0068(12) 0.0064(12) C5 0.0198(14) 0.0323(16) 0.0294(14) -0.0010(13) -0.0008(11) 0.0008(12) C6 0.0231(15) 0.057(2) 0.0393(18) 0.0050(17) -0.0030(14) 0.0073(16) C7 0.0423(19) 0.0325(16) 0.0251(13) -0.0006(13) -0.0099(13) 0.0136(15) C8 0.0331(16) 0.0202(13) 0.0316(15) 0.0034(12) -0.0112(13) 0.0014(12) C9 0.0454(19) 0.0140(12) 0.0313(15) 0.0029(11) -0.0142(14) -0.0034(12) C10 0.045(2) 0.046(2) 0.0281(16) -0.0016(15) -0.0049(14) 0.0148(17) C11 0.0381(19) 0.052(2) 0.0439(19) -0.0023(18) -0.0136(16) -0.0112(18) C12 0.069(3) 0.047(2) 0.068(3) 0.000(2) -0.017(2) -0.025(2) C13 0.078(3) 0.0360(19) 0.0370(19) 0.0031(16) -0.004(2) 0.006(2) C14 0.051(2) 0.0266(15) 0.0316(15) -0.0011(13) -0.0040(15) 0.0025(15) C15 0.055(3) 0.047(2) 0.043(2) 0.0026(17) -0.0062(18) 0.0029(19) C16 0.058(2) 0.0328(17) 0.0334(16) -0.0036(14) -0.0078(16) 0.0040(17) C17 0.112(5) 0.059(3) 0.047(2) -0.018(2) -0.016(3) 0.012(3) C18 0.081(3) 0.043(2) 0.049(2) 0.0070(18) -0.016(2) 0.016(2) _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 C2 1.208(5) . ? O2 C2 1.332(4) . ? O2 C1 1.443(6) . ? O3 C5 1.214(4) . ? O4 C7 1.203(4) . ? N1 C5 1.374(4) . ? N1 C7 1.374(4) . ? N1 C6 1.452(4) . ? C2 C3 1.495(6) . ? C3 C4 1.526(5) . ? C4 C5 1.515(4) . ? C4 C8 1.539(4) . ? C7 C8 1.521(5) . ? C8 C9 1.528(4) . ? C9 C14 1.531(5) . ? C9 C10 1.620(5) . ? C10 C11 1.511(5) . ? C11 C16 1.533(6) . ? C11 C12 1.544(6) . ? C12 C13 1.546(8) . ? C13 C14 1.554(5) . ? C14 C15 1.488(6) . ? C14 C16 1.577(5) . ? C16 C18 1.510(6) . ? C16 C17 1.528(6) . ? 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 O2 C1 115.1(3) . . ? C5 N1 C7 112.5(3) . . ? C5 N1 C6 123.1(3) . . ? C7 N1 C6 123.3(3) . . ? O1 C2 O2 123.9(4) . . ? O1 C2 C3 125.5(3) . . ? O2 C2 C3 110.6(3) . . ? C2 C3 C4 113.8(3) . . ? C5 C4 C3 111.3(3) . . ? C5 C4 C8 104.2(2) . . ? C3 C4 C8 116.5(3) . . ? O3 C5 N1 123.8(3) . . ? O3 C5 C4 127.0(3) . . ? N1 C5 C4 109.1(3) . . ? O4 C7 N1 124.2(3) . . ? O4 C7 C8 126.9(3) . . ? N1 C7 C8 108.8(3) . . ? C7 C8 C9 115.7(3) . . ? C7 C8 C4 103.5(2) . . ? C9 C8 C4 109.3(2) . . ? C8 C9 C14 119.8(3) . . ? C8 C9 C10 109.1(3) . . ? C14 C9 C10 102.8(3) . . ? C11 C10 C9 101.8(3) . . ? C10 C11 C16 103.8(3) . . ? C10 C11 C12 107.0(3) . . ? C16 C11 C12 102.8(4) . . ? C11 C12 C13 103.6(4) . . ? C12 C13 C14 103.3(3) . . ? C15 C14 C9 113.2(3) . . ? C15 C14 C13 116.2(3) . . ? C9 C14 C13 109.0(3) . . ? C15 C14 C16 115.0(3) . . ? C9 C14 C16 101.4(3) . . ? C13 C14 C16 100.3(3) . . ? C18 C16 C17 107.8(4) . . ? C18 C16 C11 113.1(4) . . ? C17 C16 C11 114.1(4) . . ? C18 C16 C14 114.2(3) . . ? C17 C16 C14 113.6(3) . . ? C11 C16 C14 93.6(3) . . ? 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 C1 O2 C2 O1 -3.0(5) . . . . ? C1 O2 C2 C3 175.8(3) . . . . ? O1 C2 C3 C4 -1.8(6) . . . . ? O2 C2 C3 C4 179.3(3) . . . . ? C2 C3 C4 C5 -61.6(4) . . . . ? C2 C3 C4 C8 57.6(4) . . . . ? C7 N1 C5 O3 177.4(3) . . . . ? C6 N1 C5 O3 8.7(5) . . . . ? C7 N1 C5 C4 -3.3(4) . . . . ? C6 N1 C5 C4 -172.0(3) . . . . ? C3 C4 C5 O3 -59.8(5) . . . . ? C8 C4 C5 O3 173.9(3) . . . . ? C3 C4 C5 N1 120.9(3) . . . . ? C8 C4 C5 N1 -5.4(3) . . . . ? C5 N1 C7 O4 -167.5(4) . . . . ? C6 N1 C7 O4 1.1(5) . . . . ? C5 N1 C7 C8 10.9(4) . . . . ? C6 N1 C7 C8 179.5(3) . . . . ? O4 C7 C8 C9 -75.5(4) . . . . ? N1 C7 C8 C9 106.0(3) . . . . ? O4 C7 C8 C4 164.9(4) . . . . ? N1 C7 C8 C4 -13.5(3) . . . . ? C5 C4 C8 C7 11.0(3) . . . . ? C3 C4 C8 C7 -112.0(3) . . . . ? C5 C4 C8 C9 -112.9(3) . . . . ? C3 C4 C8 C9 124.1(3) . . . . ? C7 C8 C9 C14 60.3(4) . . . . ? C4 C8 C9 C14 176.6(3) . . . . ? C7 C8 C9 C10 178.2(3) . . . . ? C4 C8 C9 C10 -65.5(3) . . . . ? C8 C9 C10 C11 -128.6(3) . . . . ? C14 C9 C10 C11 -0.5(4) . . . . ? C9 C10 C11 C16 -35.9(4) . . . . ? C9 C10 C11 C12 72.4(4) . . . . ? C10 C11 C12 C13 -75.9(4) . . . . ? C16 C11 C12 C13 33.1(4) . . . . ? C11 C12 C13 C14 3.7(4) . . . . ? C8 C9 C14 C15 -80.0(4) . . . . ? C10 C9 C14 C15 159.0(3) . . . . ? C8 C9 C14 C13 51.1(4) . . . . ? C10 C9 C14 C13 -70.0(4) . . . . ? C8 C9 C14 C16 156.3(3) . . . . ? C10 C9 C14 C16 35.2(3) . . . . ? C12 C13 C14 C15 -162.4(4) . . . . ? C12 C13 C14 C9 68.2(4) . . . . ? C12 C13 C14 C16 -37.8(4) . . . . ? C10 C11 C16 C18 -61.6(4) . . . . ? C12 C11 C16 C18 -173.0(3) . . . . ? C10 C11 C16 C17 174.6(3) . . . . ? C12 C11 C16 C17 63.2(4) . . . . ? C10 C11 C16 C14 56.7(3) . . . . ? C12 C11 C16 C14 -54.8(3) . . . . ? C15 C14 C16 C18 -60.8(5) . . . . ? C9 C14 C16 C18 61.7(4) . . . . ? C13 C14 C16 C18 173.7(4) . . . . ? C15 C14 C16 C17 63.4(5) . . . . ? C9 C14 C16 C17 -174.0(4) . . . . ? C13 C14 C16 C17 -62.0(5) . . . . ? C15 C14 C16 C11 -178.2(3) . . . . ? C9 C14 C16 C11 -55.7(3) . . . . ? C13 C14 C16 C11 56.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.742 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.078 data_str0254_Structure_37b _database_code_depnum_ccdc_archive 'CCDC 238612' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H27 N O4' _chemical_formula_weight 321.41 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' 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 orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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' _cell_length_a 6.9054(5) _cell_length_b 9.2827(7) _cell_length_c 27.029(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1732.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9598 _exptl_absorpt_correction_T_max 0.9931 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15430 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4169 _reflns_number_gt 3589 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0798P)^2^+0.1483P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(16) _refine_ls_number_reflns 4169 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1513 _refine_ls_wR_factor_gt 0.1452 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _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 0.6666(4) 0.58566(18) 0.06569(7) 0.0809(6) Uani 1 1 d . . . O2 O 0.5669(3) 0.5398(2) -0.01082(6) 0.0711(5) Uani 1 1 d . . . O3 O 1.1575(3) 0.4295(2) 0.05247(7) 0.0804(6) Uani 1 1 d . . . O4 O 0.7925(4) 0.4886(2) 0.18920(6) 0.0793(6) Uani 1 1 d . . . N1 N 1.0166(3) 0.46543(18) 0.12792(6) 0.0499(4) Uani 1 1 d . . . C1 C 0.4688(5) 0.6768(3) -0.01193(15) 0.0959(11) Uani 1 1 d . . . H1A H 0.4097 0.6902 -0.0437 0.144 Uiso 1 1 calc R . . H1B H 0.5605 0.7526 -0.0061 0.144 Uiso 1 1 calc R . . H1C H 0.3709 0.6788 0.0133 0.144 Uiso 1 1 calc R . . C2 C 0.6561(4) 0.5063(2) 0.03123(8) 0.0548(6) Uani 1 1 d . . . C3 C 0.7399(4) 0.3587(2) 0.02828(7) 0.0547(6) Uani 1 1 d . . . H3A H 0.8238 0.3541 -0.0005 0.066 Uiso 1 1 calc R . . H3B H 0.6350 0.2909 0.0230 0.066 Uiso 1 1 calc R . . C4 C 0.8555(3) 0.3099(2) 0.07353(6) 0.0414(4) Uani 1 1 d . . . H4A H 0.9027 0.2120 0.0673 0.050 Uiso 1 1 calc R . . C5 C 1.0286(3) 0.4058(2) 0.08169(8) 0.0495(5) Uani 1 1 d . . . C6 C 1.1514(5) 0.5735(3) 0.14627(11) 0.0744(8) Uani 1 1 d . . . H6A H 1.2603 0.5800 0.1243 0.112 Uiso 1 1 calc R . . H6B H 1.1954 0.5465 0.1787 0.112 Uiso 1 1 calc R . . H6C H 1.0875 0.6652 0.1480 0.112 Uiso 1 1 calc R . . C7 C 0.8456(4) 0.4310(2) 0.15193(7) 0.0505(5) Uani 1 1 d . . . C8 C 0.7480(3) 0.30962(19) 0.12363(6) 0.0388(4) Uani 1 1 d . . . H8A H 0.6102 0.3304 0.1189 0.047 Uiso 1 1 calc R . . C9 C 0.7751(3) 0.16487(19) 0.15157(6) 0.0371(4) Uani 1 1 d . . . H9A H 0.9085 0.1335 0.1455 0.045 Uiso 1 1 calc R . . C10 C 0.7469(3) 0.1681(3) 0.20890(7) 0.0513(6) Uani 1 1 d . . . H10A H 0.8704 0.1624 0.2259 0.062 Uiso 1 1 calc R . . H10B H 0.6803 0.2551 0.2192 0.062 Uiso 1 1 calc R . . C11 C 0.6241(3) 0.0350(3) 0.21913(7) 0.0530(5) Uani 1 1 d . . . H11A H 0.5638 0.0339 0.2520 0.064 Uiso 1 1 calc R . . C12 C 0.7462(5) -0.0980(3) 0.20771(10) 0.0717(8) Uani 1 1 d . . . H12A H 0.6851 -0.1847 0.2202 0.086 Uiso 1 1 calc R . . H12B H 0.8747 -0.0896 0.2219 0.086 Uiso 1 1 calc R . . C13 C 0.7550(4) -0.0991(2) 0.15051(9) 0.0590(6) Uani 1 1 d . . . H13A H 0.8878 -0.0938 0.1389 0.071 Uiso 1 1 calc R . . H13B H 0.6948 -0.1851 0.1372 0.071 Uiso 1 1 calc R . . C14 C 0.6402(3) 0.0376(2) 0.13569(6) 0.0385(4) Uani 1 1 d . . . C15 C 0.5688(4) 0.0360(2) 0.08308(7) 0.0517(5) Uani 1 1 d . . . H15A H 0.4874 -0.0465 0.0780 0.077 Uiso 1 1 calc R . . H15B H 0.6774 0.0314 0.0609 0.077 Uiso 1 1 calc R . . H15C H 0.4961 0.1222 0.0767 0.077 Uiso 1 1 calc R . . C16 C 0.4788(3) 0.0395(2) 0.17597(7) 0.0474(5) Uani 1 1 d . . . C17 C 0.3476(4) 0.1712(3) 0.17521(10) 0.0650(7) Uani 1 1 d . . . H17A H 0.2532 0.1634 0.2012 0.097 Uiso 1 1 calc R . . H17B H 0.2828 0.1769 0.1438 0.097 Uiso 1 1 calc R . . H17C H 0.4239 0.2565 0.1802 0.097 Uiso 1 1 calc R . . C18 C 0.3451(4) -0.0933(3) 0.17449(11) 0.0748(8) Uani 1 1 d . . . H18A H 0.2495 -0.0856 0.2001 0.112 Uiso 1 1 calc R . . H18B H 0.4206 -0.1789 0.1795 0.112 Uiso 1 1 calc R . . H18C H 0.2819 -0.0983 0.1429 0.112 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 0.1192(17) 0.0508(9) 0.0729(12) -0.0098(9) -0.0300(12) 0.0039(11) O2 0.0785(12) 0.0730(11) 0.0619(10) 0.0074(9) -0.0200(9) 0.0000(10) O3 0.0793(12) 0.0856(13) 0.0763(12) -0.0063(10) 0.0329(10) -0.0340(12) O4 0.1185(16) 0.0623(10) 0.0571(10) -0.0251(8) 0.0273(11) -0.0222(11) N1 0.0594(10) 0.0398(8) 0.0505(10) 0.0000(7) -0.0026(8) -0.0139(9) C1 0.091(2) 0.082(2) 0.115(3) 0.0117(19) -0.037(2) 0.0101(19) C2 0.0633(13) 0.0516(12) 0.0495(12) 0.0054(9) -0.0062(10) -0.0194(11) C3 0.0835(16) 0.0479(11) 0.0326(9) 0.0008(8) -0.0013(10) -0.0136(12) C4 0.0583(12) 0.0338(8) 0.0322(8) -0.0021(7) 0.0079(9) -0.0087(9) C5 0.0590(13) 0.0433(10) 0.0462(11) 0.0027(9) 0.0099(10) -0.0093(10) C6 0.0865(18) 0.0586(14) 0.0779(17) -0.0046(12) -0.0138(16) -0.0308(14) C7 0.0730(14) 0.0390(10) 0.0395(10) -0.0040(8) 0.0068(10) -0.0104(10) C8 0.0454(10) 0.0384(9) 0.0325(8) -0.0011(7) 0.0029(8) -0.0072(9) C9 0.0357(9) 0.0421(9) 0.0336(8) 0.0026(7) -0.0022(7) -0.0074(8) C10 0.0552(13) 0.0678(14) 0.0309(9) 0.0033(9) -0.0052(9) -0.0200(12) C11 0.0578(12) 0.0677(13) 0.0335(9) 0.0126(9) -0.0015(9) -0.0181(12) C12 0.0806(19) 0.0700(16) 0.0646(15) 0.0274(13) -0.0151(15) -0.0072(16) C13 0.0686(15) 0.0427(11) 0.0657(14) 0.0097(10) -0.0023(13) 0.0030(11) C14 0.0460(9) 0.0351(8) 0.0343(8) 0.0007(7) -0.0011(8) -0.0052(9) C15 0.0682(13) 0.0480(11) 0.0388(10) -0.0051(9) -0.0068(9) -0.0146(11) C16 0.0451(10) 0.0568(12) 0.0403(10) 0.0035(9) 0.0001(8) -0.0176(10) C17 0.0440(12) 0.0841(17) 0.0667(15) -0.0014(13) 0.0125(12) 0.0017(13) C18 0.0686(16) 0.0883(19) 0.0675(16) 0.0092(14) -0.0025(14) -0.0448(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 O1 C2 1.190(3) . ? O2 C2 1.330(3) . ? O2 C1 1.441(4) . ? O3 C5 1.210(3) . ? O4 C7 1.198(3) . ? N1 C5 1.369(3) . ? N1 C7 1.385(3) . ? N1 C6 1.455(3) . ? C2 C3 1.490(3) . ? C3 C4 1.530(3) . ? C4 C5 1.506(3) . ? C4 C8 1.544(3) . ? C7 C8 1.519(3) . ? C8 C9 1.553(2) . ? C9 C10 1.562(3) . ? C9 C14 1.565(2) . ? C10 C11 1.523(3) . ? C11 C12 1.526(4) . ? C11 C16 1.540(3) . ? C12 C13 1.547(4) . ? C13 C14 1.548(3) . ? C14 C15 1.505(3) . ? C14 C16 1.558(3) . ? C16 C17 1.522(4) . ? C16 C18 1.541(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 C2 O2 C1 116.2(2) . . ? C5 N1 C7 112.68(18) . . ? C5 N1 C6 123.5(2) . . ? C7 N1 C6 123.0(2) . . ? O1 C2 O2 123.6(2) . . ? O1 C2 C3 126.0(2) . . ? O2 C2 C3 110.43(19) . . ? C2 C3 C4 115.62(17) . . ? C5 C4 C3 110.86(16) . . ? C5 C4 C8 104.70(15) . . ? C3 C4 C8 116.79(19) . . ? O3 C5 N1 124.5(2) . . ? O3 C5 C4 126.5(2) . . ? N1 C5 C4 108.96(17) . . ? O4 C7 N1 123.5(2) . . ? O4 C7 C8 128.2(2) . . ? N1 C7 C8 108.27(16) . . ? C7 C8 C4 103.14(15) . . ? C7 C8 C9 110.07(15) . . ? C4 C8 C9 111.71(15) . . ? C8 C9 C10 116.81(16) . . ? C8 C9 C14 116.65(15) . . ? C10 C9 C14 102.24(14) . . ? C11 C10 C9 103.54(16) . . ? C10 C11 C12 108.15(19) . . ? C10 C11 C16 101.72(16) . . ? C12 C11 C16 103.24(19) . . ? C11 C12 C13 103.23(18) . . ? C14 C13 C12 103.5(2) . . ? C15 C14 C13 113.85(17) . . ? C15 C14 C16 115.19(18) . . ? C13 C14 C16 101.26(16) . . ? C15 C14 C9 117.47(15) . . ? C13 C14 C9 104.07(16) . . ? C16 C14 C9 103.03(14) . . ? C17 C16 C11 114.85(19) . . ? C17 C16 C18 106.6(2) . . ? C11 C16 C18 112.84(19) . . ? C17 C16 C14 115.22(17) . . ? C11 C16 C14 93.58(16) . . ? C18 C16 C14 113.64(19) . . ? 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 C1 O2 C2 O1 -4.2(4) . . . . ? C1 O2 C2 C3 176.3(2) . . . . ? O1 C2 C3 C4 -2.4(4) . . . . ? O2 C2 C3 C4 177.1(2) . . . . ? C2 C3 C4 C5 -61.8(2) . . . . ? C2 C3 C4 C8 58.0(3) . . . . ? C7 N1 C5 O3 174.3(2) . . . . ? C6 N1 C5 O3 4.6(4) . . . . ? C7 N1 C5 C4 -4.8(2) . . . . ? C6 N1 C5 C4 -174.4(2) . . . . ? C3 C4 C5 O3 -57.5(3) . . . . ? C8 C4 C5 O3 175.7(2) . . . . ? C3 C4 C5 N1 121.6(2) . . . . ? C8 C4 C5 N1 -5.2(2) . . . . ? C5 N1 C7 O4 -168.3(2) . . . . ? C6 N1 C7 O4 1.4(4) . . . . ? C5 N1 C7 C8 13.0(2) . . . . ? C6 N1 C7 C8 -177.3(2) . . . . ? O4 C7 C8 C4 166.2(3) . . . . ? N1 C7 C8 C4 -15.2(2) . . . . ? O4 C7 C8 C9 -74.4(3) . . . . ? N1 C7 C8 C9 104.12(19) . . . . ? C5 C4 C8 C7 12.0(2) . . . . ? C3 C4 C8 C7 -111.05(19) . . . . ? C5 C4 C8 C9 -106.21(17) . . . . ? C3 C4 C8 C9 130.76(17) . . . . ? C7 C8 C9 C10 43.0(2) . . . . ? C4 C8 C9 C10 156.95(17) . . . . ? C7 C8 C9 C14 164.30(17) . . . . ? C4 C8 C9 C14 -81.7(2) . . . . ? C8 C9 C10 C11 135.35(19) . . . . ? C14 C9 C10 C11 6.7(2) . . . . ? C9 C10 C11 C12 67.2(2) . . . . ? C9 C10 C11 C16 -41.1(2) . . . . ? C10 C11 C12 C13 -73.1(2) . . . . ? C16 C11 C12 C13 34.2(2) . . . . ? C11 C12 C13 C14 1.5(3) . . . . ? C12 C13 C14 C15 -160.2(2) . . . . ? C12 C13 C14 C16 -36.0(2) . . . . ? C12 C13 C14 C9 70.7(2) . . . . ? C8 C9 C14 C15 28.4(3) . . . . ? C10 C9 C14 C15 157.09(19) . . . . ? C8 C9 C14 C13 155.26(17) . . . . ? C10 C9 C14 C13 -76.03(19) . . . . ? C8 C9 C14 C16 -99.40(18) . . . . ? C10 C9 C14 C16 29.3(2) . . . . ? C10 C11 C16 C17 -62.7(2) . . . . ? C12 C11 C16 C17 -174.74(19) . . . . ? C10 C11 C16 C18 174.8(2) . . . . ? C12 C11 C16 C18 62.8(2) . . . . ? C10 C11 C16 C14 57.29(19) . . . . ? C12 C11 C16 C14 -54.77(18) . . . . ? C15 C14 C16 C17 -62.2(2) . . . . ? C13 C14 C16 C17 174.45(19) . . . . ? C9 C14 C16 C17 67.0(2) . . . . ? C15 C14 C16 C11 178.10(18) . . . . ? C13 C14 C16 C11 54.79(18) . . . . ? C9 C14 C16 C11 -52.70(18) . . . . ? C15 C14 C16 C18 61.2(2) . . . . ? C13 C14 C16 C18 -62.1(2) . . . . ? C9 C14 C16 C18 -169.56(18) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.245 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.037 data_str0241_Structure_38a _database_code_depnum_ccdc_archive 'CCDC 238613' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H28 O6' _chemical_formula_weight 352.41 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' _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 16.5381(12) _cell_length_b 11.3348(8) _cell_length_c 19.0816(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3577.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9643 _exptl_absorpt_correction_T_max 0.9942 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29906 _diffrn_reflns_av_R_equivalents 0.0786 _diffrn_reflns_av_sigmaI/netI 0.0522 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 28.31 _reflns_number_total 4366 _reflns_number_gt 3387 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0463P)^2^+2.8191P] 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 4366 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1113 _refine_ls_R_factor_gt 0.0803 _refine_ls_wR_factor_ref 0.1543 _refine_ls_wR_factor_gt 0.1423 _refine_ls_goodness_of_fit_ref 1.174 _refine_ls_restrained_S_all 1.174 _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 0.49554(10) 0.45804(17) 0.39079(10) 0.0338(5) Uani 1 1 d . . . O2 O 0.43209(11) 0.28675(16) 0.41115(10) 0.0327(5) Uani 1 1 d . . . O3 O 0.25183(10) 0.23197(13) 0.45357(8) 0.0193(4) Uani 1 1 d . . . O4 O 0.28415(10) 0.40971(15) 0.49576(9) 0.0239(4) Uani 1 1 d . . . O5 O 0.22907(10) 0.60865(14) 0.25629(8) 0.0218(4) Uani 1 1 d . . . O6 O 0.24245(11) 0.42048(15) 0.22375(9) 0.0272(4) Uani 1 1 d . . . C1 C 0.57089(16) 0.4066(3) 0.41324(16) 0.0418(8) Uani 1 1 d . . . H1A H 0.6139 0.4659 0.4103 0.063 Uiso 1 1 calc R . . H1B H 0.5843 0.3396 0.3829 0.063 Uiso 1 1 calc R . . H1C H 0.5658 0.3794 0.4618 0.063 Uiso 1 1 calc R . . C2 C 0.43062(15) 0.3873(2) 0.39191(12) 0.0230(5) Uani 1 1 d . . . C3 C 0.35834(14) 0.4530(2) 0.36537(13) 0.0225(5) Uani 1 1 d . . . H3A H 0.3676 0.4742 0.3157 0.027 Uiso 1 1 calc R . . H3B H 0.3527 0.5272 0.3923 0.027 Uiso 1 1 calc R . . C4 C 0.27915(14) 0.3834(2) 0.37085(12) 0.0185(5) Uani 1 1 d . . . H4A H 0.2826 0.3116 0.3405 0.022 Uiso 1 1 calc R . . C5 C 0.27155(12) 0.3460(2) 0.44675(12) 0.0162(5) Uani 1 1 d . . . C6 C 0.25215(17) 0.1902(2) 0.52514(13) 0.0283(6) Uani 1 1 d . . . H6A H 0.2374 0.1065 0.5261 0.042 Uiso 1 1 calc R . . H6B H 0.2130 0.2355 0.5527 0.042 Uiso 1 1 calc R . . H6C H 0.3063 0.2003 0.5452 0.042 Uiso 1 1 calc R . . C7 C 0.20913(13) 0.4635(2) 0.34435(12) 0.0174(5) Uani 1 1 d . . . H7A H 0.2117 0.5390 0.3714 0.021 Uiso 1 1 calc R . . C8 C 0.22884(13) 0.4921(2) 0.26856(12) 0.0181(5) Uani 1 1 d . . . C9 C 0.24425(17) 0.6412(2) 0.18429(13) 0.0288(6) Uani 1 1 d . . . H9A H 0.2434 0.7274 0.1799 0.043 Uiso 1 1 calc R . . H9B H 0.2023 0.6071 0.1542 0.043 Uiso 1 1 calc R . . H9C H 0.2973 0.6113 0.1699 0.043 Uiso 1 1 calc R . . C10 C 0.12084(14) 0.4164(2) 0.34948(12) 0.0173(5) Uani 1 1 d . . . C11 C 0.09148(14) 0.4205(2) 0.42610(12) 0.0197(5) Uani 1 1 d . . . H11A H 0.1259 0.3685 0.4552 0.024 Uiso 1 1 calc R . . H11B H 0.0966 0.5020 0.4443 0.024 Uiso 1 1 calc R . . C12 C 0.11110(14) 0.29012(19) 0.32148(12) 0.0182(5) Uani 1 1 d . . . H12A H 0.1286 0.2869 0.2719 0.022 Uiso 1 1 calc R . . H12B H 0.1458 0.2358 0.3488 0.022 Uiso 1 1 calc R . . C13 C 0.06512(14) 0.4990(2) 0.30671(12) 0.0202(5) Uani 1 1 d . . . H13A H 0.0702 0.5807 0.3245 0.024 Uiso 1 1 calc R . . H13B H 0.0821 0.4985 0.2570 0.024 Uiso 1 1 calc R . . C14 C 0.00291(14) 0.3805(2) 0.43156(13) 0.0230(5) Uani 1 1 d . . . H14A H -0.0146 0.3827 0.4817 0.028 Uiso 1 1 calc R . . C15 C -0.00404(15) 0.2542(2) 0.40371(13) 0.0242(5) Uani 1 1 d . . . H15A H 0.0305 0.2010 0.4319 0.029 Uiso 1 1 calc R . . H15B H -0.0607 0.2268 0.4077 0.029 Uiso 1 1 calc R . . C16 C 0.02250(15) 0.2507(2) 0.32714(13) 0.0234(5) Uani 1 1 d . . . H16A H 0.0172 0.1683 0.3089 0.028 Uiso 1 1 calc R . . C17 C -0.03092(15) 0.3330(2) 0.28380(14) 0.0262(6) Uani 1 1 d . . . H17A H -0.0880 0.3070 0.2866 0.031 Uiso 1 1 calc R . . H17B H -0.0140 0.3308 0.2340 0.031 Uiso 1 1 calc R . . C18 C -0.02306(14) 0.4591(2) 0.31223(13) 0.0236(5) Uani 1 1 d . . . H18A H -0.0578 0.5131 0.2837 0.028 Uiso 1 1 calc R . . C19 C -0.05068(15) 0.4631(2) 0.38826(13) 0.0260(6) Uani 1 1 d . . . H19A H -0.1079 0.4379 0.3917 0.031 Uiso 1 1 calc R . . H19B H -0.0464 0.5447 0.4064 0.031 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 0.0185(9) 0.0382(11) 0.0449(12) 0.0114(9) -0.0058(8) -0.0052(8) O2 0.0244(10) 0.0296(10) 0.0442(12) 0.0124(9) -0.0019(8) 0.0032(8) O3 0.0220(8) 0.0169(8) 0.0190(8) 0.0015(6) -0.0011(7) -0.0036(7) O4 0.0291(9) 0.0208(9) 0.0216(9) -0.0037(7) -0.0020(7) -0.0024(7) O5 0.0285(10) 0.0185(8) 0.0183(8) 0.0008(7) 0.0003(7) -0.0015(7) O6 0.0400(11) 0.0208(9) 0.0209(9) -0.0025(7) 0.0060(8) 0.0017(8) C1 0.0188(14) 0.062(2) 0.0448(18) 0.0180(16) -0.0063(12) -0.0041(13) C2 0.0195(12) 0.0307(14) 0.0187(12) 0.0025(10) 0.0026(10) 0.0004(10) C3 0.0203(12) 0.0237(13) 0.0234(12) 0.0060(10) 0.0010(10) 0.0003(10) C4 0.0173(12) 0.0179(11) 0.0204(11) 0.0005(9) 0.0019(9) 0.0011(9) C5 0.0104(11) 0.0180(11) 0.0203(12) 0.0009(9) 0.0004(9) 0.0012(8) C6 0.0365(15) 0.0248(14) 0.0237(13) 0.0071(11) -0.0035(12) -0.0071(11) C7 0.0184(12) 0.0161(11) 0.0178(11) -0.0013(9) -0.0009(9) 0.0011(9) C8 0.0152(11) 0.0167(11) 0.0223(12) 0.0020(9) -0.0016(9) -0.0004(9) C9 0.0426(16) 0.0216(13) 0.0221(13) 0.0046(10) 0.0016(12) -0.0024(11) C10 0.0173(11) 0.0161(11) 0.0186(11) -0.0016(9) 0.0000(9) 0.0021(9) C11 0.0167(11) 0.0238(12) 0.0186(12) -0.0045(10) -0.0008(9) 0.0038(9) C12 0.0202(12) 0.0180(11) 0.0163(11) -0.0007(9) -0.0003(9) 0.0002(9) C13 0.0202(12) 0.0218(12) 0.0186(12) 0.0020(10) -0.0009(10) 0.0022(10) C14 0.0196(12) 0.0320(14) 0.0175(12) 0.0005(10) 0.0038(9) 0.0025(10) C15 0.0189(12) 0.0269(13) 0.0269(13) 0.0055(11) 0.0028(10) -0.0028(10) C16 0.0243(13) 0.0213(12) 0.0247(13) -0.0015(10) 0.0003(10) -0.0049(10) C17 0.0216(13) 0.0318(14) 0.0253(13) 0.0016(11) -0.0041(11) -0.0050(11) C18 0.0189(12) 0.0269(13) 0.0250(13) 0.0038(10) -0.0057(10) 0.0021(10) C19 0.0165(12) 0.0293(14) 0.0320(14) -0.0008(11) 0.0024(10) 0.0018(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 C2 1.340(3) . ? O1 C1 1.441(3) . ? O2 C2 1.198(3) . ? O3 C5 1.339(3) . ? O3 C6 1.445(3) . ? O4 C5 1.200(3) . ? O5 C8 1.341(3) . ? O5 C9 1.445(3) . ? O6 C8 1.201(3) . ? C2 C3 1.497(3) . ? C3 C4 1.532(3) . ? C4 C5 1.514(3) . ? C4 C7 1.556(3) . ? C7 C8 1.517(3) . ? C7 C10 1.558(3) . ? C10 C12 1.537(3) . ? C10 C11 1.541(3) . ? C10 C13 1.546(3) . ? C11 C14 1.537(3) . ? C12 C16 1.536(3) . ? C13 C18 1.530(3) . ? C14 C19 1.531(3) . ? C14 C15 1.531(4) . ? C15 C16 1.526(3) . ? C16 C17 1.528(3) . ? C17 C18 1.534(3) . ? C18 C19 1.522(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 C2 O1 C1 116.5(2) . . ? C5 O3 C6 114.01(18) . . ? C8 O5 C9 114.72(18) . . ? O2 C2 O1 123.9(2) . . ? O2 C2 C3 126.4(2) . . ? O1 C2 C3 109.7(2) . . ? C2 C3 C4 113.8(2) . . ? C5 C4 C3 106.28(19) . . ? C5 C4 C7 114.35(18) . . ? C3 C4 C7 108.25(18) . . ? O4 C5 O3 123.2(2) . . ? O4 C5 C4 124.2(2) . . ? O3 C5 C4 112.53(19) . . ? C8 C7 C4 105.93(18) . . ? C8 C7 C10 109.54(18) . . ? C4 C7 C10 118.48(19) . . ? O6 C8 O5 122.8(2) . . ? O6 C8 C7 125.1(2) . . ? O5 C8 C7 112.16(19) . . ? C12 C10 C11 108.96(19) . . ? C12 C10 C13 108.53(18) . . ? C11 C10 C13 107.13(18) . . ? C12 C10 C7 113.32(18) . . ? C11 C10 C7 110.16(18) . . ? C13 C10 C7 108.53(18) . . ? C14 C11 C10 110.84(19) . . ? C16 C12 C10 110.28(19) . . ? C18 C13 C10 110.67(19) . . ? C19 C14 C15 109.9(2) . . ? C19 C14 C11 109.5(2) . . ? C15 C14 C11 108.90(19) . . ? C16 C15 C14 109.6(2) . . ? C15 C16 C17 109.6(2) . . ? C15 C16 C12 109.5(2) . . ? C17 C16 C12 109.6(2) . . ? C16 C17 C18 109.2(2) . . ? C19 C18 C13 110.0(2) . . ? C19 C18 C17 109.8(2) . . ? C13 C18 C17 109.4(2) . . ? C18 C19 C14 108.8(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 C1 O1 C2 O2 1.1(4) . . . . ? C1 O1 C2 C3 -178.5(2) . . . . ? O2 C2 C3 C4 5.7(4) . . . . ? O1 C2 C3 C4 -174.7(2) . . . . ? C2 C3 C4 C5 54.5(3) . . . . ? C2 C3 C4 C7 177.8(2) . . . . ? C6 O3 C5 O4 -3.8(3) . . . . ? C6 O3 C5 C4 174.00(19) . . . . ? C3 C4 C5 O4 44.8(3) . . . . ? C7 C4 C5 O4 -74.5(3) . . . . ? C3 C4 C5 O3 -132.95(19) . . . . ? C7 C4 C5 O3 107.7(2) . . . . ? C5 C4 C7 C8 179.12(19) . . . . ? C3 C4 C7 C8 60.9(2) . . . . ? C5 C4 C7 C10 -57.5(3) . . . . ? C3 C4 C7 C10 -175.7(2) . . . . ? C9 O5 C8 O6 2.0(3) . . . . ? C9 O5 C8 C7 -177.61(19) . . . . ? C4 C7 C8 O6 54.2(3) . . . . ? C10 C7 C8 O6 -74.7(3) . . . . ? C4 C7 C8 O5 -126.2(2) . . . . ? C10 C7 C8 O5 104.9(2) . . . . ? C8 C7 C10 C12 73.7(2) . . . . ? C4 C7 C10 C12 -47.8(3) . . . . ? C8 C7 C10 C11 -163.90(19) . . . . ? C4 C7 C10 C11 74.5(2) . . . . ? C8 C7 C10 C13 -46.9(2) . . . . ? C4 C7 C10 C13 -168.49(19) . . . . ? C12 C10 C11 C14 -58.1(2) . . . . ? C13 C10 C11 C14 59.1(2) . . . . ? C7 C10 C11 C14 176.99(18) . . . . ? C11 C10 C12 C16 57.9(2) . . . . ? C13 C10 C12 C16 -58.4(2) . . . . ? C7 C10 C12 C16 -179.06(19) . . . . ? C12 C10 C13 C18 58.5(2) . . . . ? C11 C10 C13 C18 -59.0(2) . . . . ? C7 C10 C13 C18 -177.92(19) . . . . ? C10 C11 C14 C19 -60.8(3) . . . . ? C10 C11 C14 C15 59.5(3) . . . . ? C19 C14 C15 C16 59.6(3) . . . . ? C11 C14 C15 C16 -60.4(3) . . . . ? C14 C15 C16 C17 -59.4(3) . . . . ? C14 C15 C16 C12 61.0(3) . . . . ? C10 C12 C16 C15 -59.9(2) . . . . ? C10 C12 C16 C17 60.4(3) . . . . ? C15 C16 C17 C18 59.7(3) . . . . ? C12 C16 C17 C18 -60.6(3) . . . . ? C10 C13 C18 C19 60.9(3) . . . . ? C10 C13 C18 C17 -59.8(2) . . . . ? C16 C17 C18 C19 -60.6(3) . . . . ? C16 C17 C18 C13 60.2(3) . . . . ? C13 C18 C19 C14 -60.0(3) . . . . ? C17 C18 C19 C14 60.4(3) . . . . ? C15 C14 C19 C18 -59.9(3) . . . . ? C11 C14 C19 C18 59.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.342 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.058 data_str0205 #(Structure 46) _database_code_depnum_ccdc_archive 'CCDC 238614' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H26 N2 O6' _chemical_formula_weight 378.42 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 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 18.717(3) _cell_length_b 10.0246(14) _cell_length_c 19.808(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3716.6(10) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9419 _exptl_absorpt_correction_T_max 0.9910 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31099 _diffrn_reflns_av_R_equivalents 0.0598 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4548 _reflns_number_gt 3899 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0502P)^2^+2.3298P] 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 4548 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0629 _refine_ls_wR_factor_ref 0.1391 _refine_ls_wR_factor_gt 0.1334 _refine_ls_goodness_of_fit_ref 1.171 _refine_ls_restrained_S_all 1.171 _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 N1 N 0.87139(8) 0.98308(15) 0.03114(8) 0.0214(3) Uani 1 1 d . . . N2 N 0.85327(9) 0.38568(16) 0.20200(8) 0.0244(4) Uani 1 1 d . . . O1 O 0.89356(8) 0.50941(15) -0.06380(8) 0.0332(4) Uani 1 1 d . . . O2 O 0.83317(7) 0.69384(13) -0.03470(7) 0.0236(3) Uani 1 1 d . . . O3 O 0.94480(8) 0.95156(15) -0.06015(7) 0.0290(3) Uani 1 1 d . . . O4 O 0.80731(7) 0.95685(15) 0.12848(7) 0.0290(3) Uani 1 1 d . . . O5 O 0.86558(8) 0.48313(14) 0.09878(7) 0.0281(3) Uani 1 1 d . . . O6 O 0.82235(10) 0.33315(16) 0.31048(8) 0.0431(4) Uani 1 1 d . . . C1 C 0.82751(13) 0.4537(3) -0.08922(15) 0.0478(7) Uani 1 1 d . . . H1A H 0.8035 0.5194 -0.1180 0.072 Uiso 1 1 calc R . . H1B H 0.7963 0.4304 -0.0512 0.072 Uiso 1 1 calc R . . H1C H 0.8379 0.3734 -0.1157 0.072 Uiso 1 1 calc R . . C2 C 0.88750(10) 0.63031(19) -0.03579(9) 0.0201(4) Uani 1 1 d . . . C3 C 0.95767(9) 0.67545(19) -0.00659(9) 0.0209(4) Uani 1 1 d . . . H3A H 0.9916 0.6932 -0.0438 0.025 Uiso 1 1 calc R . . H3B H 0.9778 0.6030 0.0216 0.025 Uiso 1 1 calc R . . C4 C 0.94981(9) 0.80095(17) 0.03624(8) 0.0171(3) Uani 1 1 d . . . H4A H 0.9980 0.8244 0.0546 0.021 Uiso 1 1 calc R . . C5 C 0.92339(10) 0.91773(19) -0.00509(9) 0.0202(4) Uani 1 1 d . . . C6 C 0.83555(13) 1.1029(2) 0.00659(11) 0.0341(5) Uani 1 1 d . . . H6A H 0.8351 1.1024 -0.0429 0.051 Uiso 1 1 calc R . . H6B H 0.8611 1.1820 0.0227 0.051 Uiso 1 1 calc R . . H6C H 0.7863 1.1046 0.0235 0.051 Uiso 1 1 calc R . . C7 C 0.85321(10) 0.91766(18) 0.09004(9) 0.0187(4) Uani 1 1 d . . . C8 C 0.89766(9) 0.79118(16) 0.09579(8) 0.0143(3) Uani 1 1 d . . . H8A H 0.8651 0.7142 0.0866 0.017 Uiso 1 1 calc R . . C9 C 0.93093(9) 0.76848(17) 0.16712(8) 0.0151(3) Uani 1 1 d . . . C10 C 0.96420(10) 0.89892(18) 0.19309(9) 0.0216(4) Uani 1 1 d . . . H10A H 0.9903 0.8814 0.2351 0.032 Uiso 1 1 calc R . . H10B H 0.9263 0.9643 0.2016 0.032 Uiso 1 1 calc R . . H10C H 0.9972 0.9342 0.1591 0.032 Uiso 1 1 calc R . . C11 C 0.99086(10) 0.66414(19) 0.16292(9) 0.0211(4) Uani 1 1 d . . . H11A H 1.0076 0.6426 0.2085 0.032 Uiso 1 1 calc R . . H11B H 1.0306 0.7001 0.1364 0.032 Uiso 1 1 calc R . . H11C H 0.9726 0.5832 0.1412 0.032 Uiso 1 1 calc R . . C12 C 0.87077(9) 0.72653(17) 0.21628(8) 0.0151(3) Uani 1 1 d . . . H12A H 0.8396 0.8071 0.2209 0.018 Uiso 1 1 calc R . . C13 C 0.89340(10) 0.69108(19) 0.28869(9) 0.0211(4) Uani 1 1 d . . . H13A H 0.9315 0.6225 0.2888 0.025 Uiso 1 1 calc R . . H13B H 0.9106 0.7709 0.3132 0.025 Uiso 1 1 calc R . . C14 C 0.82463(10) 0.6372(2) 0.31997(9) 0.0237(4) Uani 1 1 d . . . H14A H 0.7918 0.7106 0.3323 0.028 Uiso 1 1 calc R . . H14B H 0.8349 0.5830 0.3606 0.028 Uiso 1 1 calc R . . C15 C 0.79318(10) 0.55123(19) 0.26340(9) 0.0225(4) Uani 1 1 d . . . H15A H 0.7398 0.5496 0.2658 0.027 Uiso 1 1 calc R . . C16 C 0.81889(9) 0.61050(18) 0.19521(9) 0.0177(4) Uani 1 1 d . . . H16A H 0.7772 0.6479 0.1699 0.021 Uiso 1 1 calc R . . C17 C 0.84875(10) 0.49170(18) 0.15762(9) 0.0205(4) Uani 1 1 d . . . C18 C 0.88104(13) 0.2558(2) 0.18236(12) 0.0352(5) Uani 1 1 d . . . H18A H 0.8492 0.2155 0.1488 0.053 Uiso 1 1 calc R . . H18B H 0.8837 0.1979 0.2221 0.053 Uiso 1 1 calc R . . H18C H 0.9289 0.2665 0.1629 0.053 Uiso 1 1 calc R . . C19 C 0.82332(11) 0.4116(2) 0.26417(10) 0.0269(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 N1 0.0270(8) 0.0155(7) 0.0216(8) 0.0030(6) -0.0059(6) 0.0002(6) N2 0.0271(8) 0.0172(8) 0.0289(9) 0.0021(6) -0.0060(7) -0.0047(6) O1 0.0294(8) 0.0318(8) 0.0384(8) -0.0204(7) -0.0089(6) 0.0065(6) O2 0.0230(7) 0.0235(7) 0.0244(7) -0.0024(5) -0.0043(5) 0.0021(5) O3 0.0340(8) 0.0336(8) 0.0193(7) 0.0071(6) -0.0029(6) -0.0134(6) O4 0.0284(7) 0.0317(8) 0.0269(7) -0.0005(6) 0.0014(6) 0.0148(6) O5 0.0392(8) 0.0221(7) 0.0230(7) -0.0048(6) 0.0040(6) -0.0061(6) O6 0.0581(11) 0.0339(9) 0.0372(9) 0.0188(7) -0.0003(8) -0.0124(8) C1 0.0393(13) 0.0392(13) 0.0648(17) -0.0311(13) -0.0195(12) 0.0033(11) C2 0.0233(9) 0.0223(9) 0.0146(8) -0.0031(7) 0.0000(7) 0.0005(7) C3 0.0178(8) 0.0259(10) 0.0190(8) -0.0057(7) 0.0016(6) 0.0014(7) C4 0.0145(8) 0.0206(9) 0.0162(8) -0.0005(7) 0.0002(6) -0.0030(6) C5 0.0211(9) 0.0217(9) 0.0179(8) 0.0016(7) -0.0041(7) -0.0097(7) C6 0.0496(13) 0.0211(10) 0.0317(11) 0.0059(9) -0.0137(10) 0.0069(9) C7 0.0197(9) 0.0174(8) 0.0191(8) -0.0006(7) -0.0049(7) 0.0020(7) C8 0.0149(8) 0.0136(8) 0.0144(8) -0.0006(6) -0.0001(6) -0.0006(6) C9 0.0159(8) 0.0145(8) 0.0149(8) -0.0001(6) -0.0005(6) -0.0007(6) C10 0.0258(9) 0.0192(9) 0.0199(8) 0.0004(7) -0.0041(7) -0.0046(7) C11 0.0185(8) 0.0236(9) 0.0213(9) 0.0010(7) -0.0008(7) 0.0039(7) C12 0.0168(8) 0.0152(8) 0.0134(7) -0.0008(6) -0.0002(6) 0.0002(6) C13 0.0237(9) 0.0247(9) 0.0148(8) 0.0009(7) -0.0033(7) -0.0029(7) C14 0.0254(9) 0.0314(10) 0.0144(8) 0.0027(7) 0.0012(7) -0.0007(8) C15 0.0176(8) 0.0296(10) 0.0202(9) 0.0055(8) 0.0018(7) -0.0052(7) C16 0.0167(8) 0.0200(9) 0.0164(8) 0.0017(7) -0.0018(6) -0.0034(7) C17 0.0216(9) 0.0175(8) 0.0224(9) -0.0002(7) -0.0034(7) -0.0079(7) C18 0.0459(13) 0.0182(10) 0.0414(12) -0.0019(9) -0.0100(10) -0.0015(9) C19 0.0264(10) 0.0270(10) 0.0275(10) 0.0075(8) -0.0042(8) -0.0118(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 N1 C5 1.375(2) . ? N1 C7 1.381(2) . ? N1 C6 1.459(2) . ? N2 C19 1.378(3) . ? N2 C17 1.382(2) . ? N2 C18 1.455(3) . ? O1 C2 1.338(2) . ? O1 C1 1.447(3) . ? O2 C2 1.200(2) . ? O3 C5 1.210(2) . ? O4 C7 1.213(2) . ? O5 C17 1.210(2) . ? O6 C19 1.208(2) . ? C2 C3 1.505(2) . ? C3 C4 1.525(2) . ? C4 C5 1.512(2) . ? C4 C8 1.534(2) . ? C7 C8 1.521(2) . ? C8 C9 1.561(2) . ? C9 C11 1.536(2) . ? C9 C10 1.537(2) . ? C9 C12 1.547(2) . ? C12 C13 1.537(2) . ? C12 C16 1.572(2) . ? C13 C14 1.527(3) . ? C14 C15 1.531(3) . ? C15 C19 1.510(3) . ? C15 C16 1.552(2) . ? C16 C17 1.512(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 C5 N1 C7 112.90(15) . . ? C5 N1 C6 122.93(17) . . ? C7 N1 C6 124.00(17) . . ? C19 N2 C17 113.51(16) . . ? C19 N2 C18 123.57(17) . . ? C17 N2 C18 122.68(17) . . ? C2 O1 C1 114.95(16) . . ? O2 C2 O1 124.06(17) . . ? O2 C2 C3 124.97(17) . . ? O1 C2 C3 110.97(16) . . ? C2 C3 C4 112.21(15) . . ? C5 C4 C3 111.67(14) . . ? C5 C4 C8 104.93(14) . . ? C3 C4 C8 115.88(14) . . ? O3 C5 N1 124.82(18) . . ? O3 C5 C4 126.63(18) . . ? N1 C5 C4 108.53(15) . . ? O4 C7 N1 123.43(17) . . ? O4 C7 C8 127.61(16) . . ? N1 C7 C8 108.93(15) . . ? C7 C8 C4 103.73(13) . . ? C7 C8 C9 114.05(13) . . ? C4 C8 C9 116.84(13) . . ? C11 C9 C10 107.55(14) . . ? C11 C9 C12 112.37(14) . . ? C10 C9 C12 108.40(14) . . ? C11 C9 C8 109.98(14) . . ? C10 C9 C8 109.91(14) . . ? C12 C9 C8 108.61(13) . . ? C13 C12 C9 116.72(14) . . ? C13 C12 C16 104.29(14) . . ? C9 C12 C16 118.94(13) . . ? C14 C13 C12 103.19(14) . . ? C13 C14 C15 103.07(14) . . ? C19 C15 C14 111.78(16) . . ? C19 C15 C16 104.36(15) . . ? C14 C15 C16 107.60(14) . . ? C17 C16 C15 103.99(14) . . ? C17 C16 C12 119.03(14) . . ? C15 C16 C12 104.11(13) . . ? O5 C17 N2 122.83(18) . . ? O5 C17 C16 128.79(17) . . ? N2 C17 C16 108.37(15) . . ? O6 C19 N2 124.2(2) . . ? O6 C19 C15 127.3(2) . . ? N2 C19 C15 108.53(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 C1 O1 C2 O2 -4.4(3) . . . . ? C1 O1 C2 C3 175.97(19) . . . . ? O2 C2 C3 C4 10.4(3) . . . . ? O1 C2 C3 C4 -170.00(15) . . . . ? C2 C3 C4 C5 -62.26(19) . . . . ? C2 C3 C4 C8 57.8(2) . . . . ? C7 N1 C5 O3 175.32(17) . . . . ? C6 N1 C5 O3 0.1(3) . . . . ? C7 N1 C5 C4 -6.2(2) . . . . ? C6 N1 C5 C4 178.50(16) . . . . ? C3 C4 C5 O3 -45.5(2) . . . . ? C8 C4 C5 O3 -171.84(17) . . . . ? C3 C4 C5 N1 136.05(15) . . . . ? C8 C4 C5 N1 9.75(18) . . . . ? C5 N1 C7 O4 -178.22(17) . . . . ? C6 N1 C7 O4 -3.0(3) . . . . ? C5 N1 C7 C8 -0.1(2) . . . . ? C6 N1 C7 C8 175.10(16) . . . . ? O4 C7 C8 C4 -175.83(18) . . . . ? N1 C7 C8 C4 6.16(18) . . . . ? O4 C7 C8 C9 -47.7(2) . . . . ? N1 C7 C8 C9 134.33(15) . . . . ? C5 C4 C8 C7 -9.31(17) . . . . ? C3 C4 C8 C7 -132.95(15) . . . . ? C5 C4 C8 C9 -135.74(14) . . . . ? C3 C4 C8 C9 100.62(17) . . . . ? C7 C8 C9 C11 -163.76(14) . . . . ? C4 C8 C9 C11 -42.62(19) . . . . ? C7 C8 C9 C10 -45.53(19) . . . . ? C4 C8 C9 C10 75.60(18) . . . . ? C7 C8 C9 C12 72.90(18) . . . . ? C4 C8 C9 C12 -165.96(14) . . . . ? C11 C9 C12 C13 54.5(2) . . . . ? C10 C9 C12 C13 -64.18(19) . . . . ? C8 C9 C12 C13 176.43(14) . . . . ? C11 C9 C12 C16 -71.92(19) . . . . ? C10 C9 C12 C16 169.37(14) . . . . ? C8 C9 C12 C16 49.97(19) . . . . ? C9 C12 C13 C14 -172.62(15) . . . . ? C16 C12 C13 C14 -39.20(18) . . . . ? C12 C13 C14 C15 41.51(18) . . . . ? C13 C14 C15 C19 85.77(18) . . . . ? C13 C14 C15 C16 -28.24(19) . . . . ? C19 C15 C16 C17 10.65(18) . . . . ? C14 C15 C16 C17 129.53(15) . . . . ? C19 C15 C16 C12 -114.69(15) . . . . ? C14 C15 C16 C12 4.19(19) . . . . ? C13 C12 C16 C17 -93.78(17) . . . . ? C9 C12 C16 C17 38.4(2) . . . . ? C13 C12 C16 C15 21.35(17) . . . . ? C9 C12 C16 C15 153.50(15) . . . . ? C19 N2 C17 O5 -172.36(18) . . . . ? C18 N2 C17 O5 2.2(3) . . . . ? C19 N2 C17 C16 6.4(2) . . . . ? C18 N2 C17 C16 -179.01(17) . . . . ? C15 C16 C17 O5 168.11(19) . . . . ? C12 C16 C17 O5 -76.7(2) . . . . ? C15 C16 C17 N2 -10.57(18) . . . . ? C12 C16 C17 N2 104.62(17) . . . . ? C17 N2 C19 O6 -179.04(19) . . . . ? C18 N2 C19 O6 6.4(3) . . . . ? C17 N2 C19 C15 0.9(2) . . . . ? C18 N2 C19 C15 -173.62(17) . . . . ? C14 C15 C19 O6 56.5(3) . . . . ? C16 C15 C19 O6 172.5(2) . . . . ? C14 C15 C19 N2 -123.49(16) . . . . ? C16 C15 C19 N2 -7.49(19) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.439 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.054