Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 loop_ _publ_author_name 'Hong-Min Liu' 'Fuyi Zhang' 'Da-Peng Zou' _publ_contact_author_name 'Dr Hong-Min Liu' _publ_contact_author_address ; Department of Chemistry Zhengzhou University Zhengzhou 450052 CHINA ; _publ_contact_author_email LIUHM@ZZU.EDU.CN _publ_section_title ; Stereoselective synthesis of 2,2-bis(C-branched-chain)glucopyranosid-3- ulose via autoxidation-Michael addition reaction ; data_compound_7 _database_code_CSD 200166 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 N0 O9' _chemical_formula_weight 378.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 6.3659(13) _cell_length_b 11.591(2) _cell_length_c 23.782(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1754.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 180 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25.4 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9659 _exptl_absorpt_correction_T_max 0.9771 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 R-axis-IV _diffrn_measurement_method 'Osillation frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5999 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0747 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 27.53 _reflns_number_total 3520 _reflns_number_gt 2474 _reflns_threshold_expression >2sigma(I) _computing_data_collection raxis _computing_cell_refinement raxis _computing_data_reduction raxis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics texsan _computing_publication_material texsan _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^)+(0.0571P)^2^+0.0000P] 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 0.8(14) _refine_ls_number_reflns 3520 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0993 _refine_ls_R_factor_gt 0.0557 _refine_ls_wR_factor_ref 0.1184 _refine_ls_wR_factor_gt 0.1064 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 0.7481(4) 0.57590(17) -0.00019(8) 0.0502(6) Uani 1 1 d . . . O2 O 0.3673(4) 0.23197(17) 0.13605(10) 0.0633(7) Uani 1 1 d . . . O3 O 0.3613(4) 0.42576(15) 0.13265(8) 0.0468(6) Uani 1 1 d . . . O4 O 0.4249(3) 0.67819(15) 0.16629(8) 0.0374(5) Uani 1 1 d . . . O5 O 0.9037(3) 0.59804(15) 0.08923(8) 0.0401(5) Uani 1 1 d . . . O6 O 0.6697(3) 0.82983(15) 0.17125(9) 0.0490(5) Uani 1 1 d . . . O7 O 0.8799(4) 0.2629(2) 0.01844(11) 0.0739(8) Uani 1 1 d . . . O8 O 0.7749(4) 0.15617(16) 0.09195(9) 0.0638(7) Uani 1 1 d . . . O9 O 0.3404(4) 0.56766(19) 0.06555(9) 0.0645(7) Uani 1 1 d . . . H9A H 0.2472 0.6017 0.0826 0.097 Uiso 1 1 calc R . . C1 C 0.8268(5) 0.5189(2) 0.04691(11) 0.0401(7) Uani 1 1 d . . . H1A H 0.9391 0.4659 0.0357 0.048 Uiso 1 1 calc R . . C2 C 0.6483(5) 0.4520(2) 0.07313(10) 0.0339(6) Uani 1 1 d . . . C3 C 0.4760(5) 0.5152(2) 0.10395(11) 0.0346(7) Uani 1 1 d . . . C4 C 0.5782(5) 0.6008(2) 0.14384(11) 0.0331(6) Uani 1 1 d . . . H4A H 0.6476 0.5592 0.1745 0.040 Uiso 1 1 calc R . . C5 C 0.7403(4) 0.6713(2) 0.11102(12) 0.0355(6) Uani 1 1 d . . . H5A H 0.6707 0.7112 0.0798 0.043 Uiso 1 1 calc R . . C6 C 0.8379(5) 0.7595(2) 0.15032(14) 0.0493(8) Uani 1 1 d . . . H6A H 0.9091 0.7211 0.1811 0.059 Uiso 1 1 calc R . . H6B H 0.9392 0.8065 0.1303 0.059 Uiso 1 1 calc R . . C7 C 0.9043(8) 0.6204(4) -0.03551(17) 0.0984(17) Uani 1 1 d . . . H7A H 0.8399 0.6593 -0.0667 0.148 Uiso 1 1 calc R . . H7B H 0.9905 0.5585 -0.0492 0.148 Uiso 1 1 calc R . . H7C H 0.9896 0.6740 -0.0149 0.148 Uiso 1 1 calc R . . C8 C 0.6288(5) 0.3394(2) 0.08188(12) 0.0398(7) Uani 1 1 d . . . C9 C 0.7755(5) 0.2489(2) 0.06038(14) 0.0463(8) Uani 1 1 d . . . C10 C 0.9248(7) 0.0667(3) 0.07572(17) 0.0823(13) Uani 1 1 d . . . H10A H 0.9127 0.0024 0.1010 0.123 Uiso 1 1 calc R . . H10B H 1.0649 0.0972 0.0775 0.123 Uiso 1 1 calc R . . H10C H 0.8954 0.0417 0.0380 0.123 Uiso 1 1 calc R . . C11 C 0.5244(5) 0.7642(3) 0.20228(12) 0.0418(7) Uani 1 1 d . . . H11A H 0.5957 0.7260 0.2337 0.050 Uiso 1 1 calc R . . C12 C 0.3503(5) 0.8399(2) 0.22420(11) 0.0404(7) Uani 1 1 d . . . C13 C 0.2227(6) 0.7980(2) 0.26679(12) 0.0484(8) Uani 1 1 d . . . H13A H 0.2526 0.7266 0.2828 0.058 Uiso 1 1 calc R . . C14 C 0.0533(6) 0.8597(3) 0.28567(14) 0.0545(9) Uani 1 1 d . . . H14A H -0.0323 0.8296 0.3138 0.065 Uiso 1 1 calc R . . C15 C 0.0092(6) 0.9675(3) 0.26281(14) 0.0535(9) Uani 1 1 d . . . H15A H -0.1053 1.0100 0.2755 0.064 Uiso 1 1 calc R . . C16 C 0.1368(6) 1.0104(3) 0.22130(13) 0.0522(9) Uani 1 1 d . . . H16A H 0.1081 1.0824 0.2059 0.063 Uiso 1 1 calc R . . C17 C 0.3076(5) 0.9480(2) 0.20198(12) 0.0447(8) Uani 1 1 d . . . H17A H 0.3936 0.9786 0.1741 0.054 Uiso 1 1 calc R . . C18 C 0.4429(5) 0.3191(2) 0.11896(13) 0.0449(8) 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 O1 0.0522(15) 0.0602(12) 0.0382(10) 0.0078(10) 0.0057(11) -0.0109(12) O2 0.0698(19) 0.0388(11) 0.0812(17) 0.0020(12) 0.0307(14) -0.0121(12) O3 0.0466(15) 0.0358(9) 0.0578(12) -0.0036(10) 0.0236(11) -0.0086(10) O4 0.0331(11) 0.0356(9) 0.0435(11) -0.0063(9) 0.0024(9) -0.0011(9) O5 0.0256(12) 0.0448(11) 0.0501(12) -0.0048(10) 0.0041(10) -0.0001(9) O6 0.0365(12) 0.0392(9) 0.0714(14) -0.0144(11) 0.0035(11) -0.0031(11) O7 0.076(2) 0.0636(14) 0.0822(18) -0.0015(13) 0.0396(16) 0.0159(15) O8 0.0853(19) 0.0411(11) 0.0649(14) 0.0012(11) 0.0131(14) 0.0194(13) O9 0.0491(15) 0.0734(14) 0.0710(15) -0.0020(13) 0.0041(14) 0.0105(13) C1 0.0401(19) 0.0392(14) 0.0409(15) -0.0023(13) 0.0075(14) -0.0014(14) C2 0.0294(16) 0.0393(14) 0.0330(13) -0.0012(12) 0.0034(13) 0.0008(13) C3 0.0265(17) 0.0364(14) 0.0410(15) 0.0036(13) 0.0036(13) 0.0027(12) C4 0.0269(16) 0.0368(14) 0.0358(14) 0.0018(12) 0.0010(13) 0.0055(12) C5 0.0271(16) 0.0357(13) 0.0437(15) 0.0028(13) 0.0059(13) 0.0040(13) C6 0.0342(19) 0.0472(16) 0.066(2) -0.0140(16) 0.0024(17) -0.0039(16) C7 0.083(4) 0.148(4) 0.065(3) 0.040(3) 0.014(3) -0.039(3) C8 0.0385(18) 0.0368(14) 0.0440(16) -0.0011(13) 0.0043(14) 0.0020(14) C9 0.049(2) 0.0364(14) 0.0539(18) -0.0061(15) 0.0060(17) 0.0040(15) C10 0.094(3) 0.057(2) 0.096(3) -0.011(2) 0.000(3) 0.036(2) C11 0.0412(19) 0.0437(16) 0.0405(15) -0.0032(14) -0.0010(15) -0.0014(15) C12 0.0411(18) 0.0421(16) 0.0380(15) -0.0109(14) -0.0060(15) 0.0036(15) C13 0.052(2) 0.0465(17) 0.0462(18) -0.0043(14) 0.0011(17) -0.0065(16) C14 0.054(2) 0.055(2) 0.055(2) -0.0123(16) 0.0142(18) -0.0051(17) C15 0.045(2) 0.0564(19) 0.059(2) -0.0227(17) 0.0038(18) 0.0031(16) C16 0.060(2) 0.0457(17) 0.0512(18) -0.0110(15) -0.0073(18) 0.0100(17) C17 0.049(2) 0.0448(15) 0.0399(15) -0.0075(13) 0.0030(15) 0.0039(15) C18 0.0466(19) 0.0370(14) 0.0509(18) 0.0012(15) 0.0108(16) -0.0045(15) _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 1.394(3) . ? O1 C7 1.400(5) . ? O2 C18 1.190(3) . ? O3 C18 1.380(3) . ? O3 C3 1.440(3) . ? O4 C4 1.429(3) . ? O4 C11 1.458(3) . ? O5 C5 1.439(3) . ? O5 C1 1.447(3) . ? O6 C11 1.407(3) . ? O6 C6 1.435(4) . ? O7 C9 1.210(4) . ? O8 C9 1.311(4) . ? O8 C10 1.462(4) . ? O9 C3 1.396(3) . ? C1 C2 1.510(4) . ? C2 C8 1.327(4) . ? C2 C3 1.509(4) . ? C3 C4 1.519(4) . ? C4 C5 1.531(4) . ? C5 C6 1.518(4) . ? C8 C18 1.495(4) . ? C8 C9 1.495(4) . ? C11 C12 1.507(4) . ? C12 C17 1.386(4) . ? C12 C13 1.387(4) . ? C13 C14 1.370(5) . ? C14 C15 1.391(5) . ? C15 C16 1.371(5) . ? C16 C17 1.384(4) . ? 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 O1 C7 113.7(3) . . ? C18 O3 C3 110.0(2) . . ? C4 O4 C11 110.6(2) . . ? C5 O5 C1 112.3(2) . . ? C11 O6 C6 111.4(2) . . ? C9 O8 C10 115.4(3) . . ? O1 C1 O5 112.3(2) . . ? O1 C1 C2 107.7(3) . . ? O5 C1 C2 107.0(2) . . ? C8 C2 C3 109.5(3) . . ? C8 C2 C1 129.8(3) . . ? C3 C2 C1 119.9(2) . . ? O9 C3 O3 108.1(2) . . ? O9 C3 C2 110.1(2) . . ? O3 C3 C2 104.4(2) . . ? O9 C3 C4 112.9(2) . . ? O3 C3 C4 113.0(2) . . ? C2 C3 C4 108.0(2) . . ? O4 C4 C3 110.6(2) . . ? O4 C4 C5 108.39(19) . . ? C3 C4 C5 108.6(2) . . ? O5 C5 C6 108.8(2) . . ? O5 C5 C4 110.8(2) . . ? C6 C5 C4 108.8(2) . . ? O6 C6 C5 106.9(2) . . ? C2 C8 C18 108.8(2) . . ? C2 C8 C9 125.3(3) . . ? C18 C8 C9 125.9(2) . . ? O7 C9 O8 125.7(3) . . ? O7 C9 C8 122.1(3) . . ? O8 C9 C8 112.2(3) . . ? O6 C11 O4 110.3(2) . . ? O6 C11 C12 110.5(2) . . ? O4 C11 C12 106.4(2) . . ? C17 C12 C13 118.7(3) . . ? C17 C12 C11 122.6(3) . . ? C13 C12 C11 118.6(3) . . ? C14 C13 C12 121.1(3) . . ? C13 C14 C15 120.0(3) . . ? C16 C15 C14 119.1(3) . . ? C15 C16 C17 121.0(3) . . ? C16 C17 C12 120.0(3) . . ? O2 C18 O3 121.8(3) . . ? O2 C18 C8 130.9(3) . . ? O3 C18 C8 107.2(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 O1 C1 O5 75.7(4) . . . . ? C7 O1 C1 C2 -166.7(3) . . . . ? C5 O5 C1 O1 62.5(3) . . . . ? C5 O5 C1 C2 -55.5(3) . . . . ? O1 C1 C2 C8 119.8(3) . . . . ? O5 C1 C2 C8 -119.2(3) . . . . ? O1 C1 C2 C3 -72.2(3) . . . . ? O5 C1 C2 C3 48.8(3) . . . . ? C18 O3 C3 O9 113.9(3) . . . . ? C18 O3 C3 C2 -3.2(3) . . . . ? C18 O3 C3 C4 -120.4(3) . . . . ? C8 C2 C3 O9 -113.9(3) . . . . ? C1 C2 C3 O9 75.8(3) . . . . ? C8 C2 C3 O3 1.9(3) . . . . ? C1 C2 C3 O3 -168.4(2) . . . . ? C8 C2 C3 C4 122.4(3) . . . . ? C1 C2 C3 C4 -47.8(3) . . . . ? C11 O4 C4 C3 -177.0(2) . . . . ? C11 O4 C4 C5 -58.1(3) . . . . ? O9 C3 C4 O4 47.1(3) . . . . ? O3 C3 C4 O4 -76.0(3) . . . . ? C2 C3 C4 O4 169.0(2) . . . . ? O9 C3 C4 C5 -71.7(3) . . . . ? O3 C3 C4 C5 165.2(2) . . . . ? C2 C3 C4 C5 50.2(3) . . . . ? C1 O5 C5 C6 -174.1(2) . . . . ? C1 O5 C5 C4 66.3(3) . . . . ? O4 C4 C5 O5 177.7(2) . . . . ? C3 C4 C5 O5 -62.1(3) . . . . ? O4 C4 C5 C6 58.1(3) . . . . ? C3 C4 C5 C6 178.2(2) . . . . ? C11 O6 C6 C5 62.1(3) . . . . ? O5 C5 C6 O6 -179.6(2) . . . . ? C4 C5 C6 O6 -58.7(3) . . . . ? C3 C2 C8 C18 0.1(3) . . . . ? C1 C2 C8 C18 169.1(3) . . . . ? C3 C2 C8 C9 -177.2(3) . . . . ? C1 C2 C8 C9 -8.2(5) . . . . ? C10 O8 C9 O7 4.0(5) . . . . ? C10 O8 C9 C8 -176.1(3) . . . . ? C2 C8 C9 O7 -26.3(5) . . . . ? C18 C8 C9 O7 156.9(3) . . . . ? C2 C8 C9 O8 153.8(3) . . . . ? C18 C8 C9 O8 -23.0(4) . . . . ? C6 O6 C11 O4 -63.1(3) . . . . ? C6 O6 C11 C12 179.6(2) . . . . ? C4 O4 C11 O6 60.9(3) . . . . ? C4 O4 C11 C12 -179.3(2) . . . . ? O6 C11 C12 C17 18.6(4) . . . . ? O4 C11 C12 C17 -101.2(3) . . . . ? O6 C11 C12 C13 -164.0(3) . . . . ? O4 C11 C12 C13 76.2(3) . . . . ? C17 C12 C13 C14 2.0(4) . . . . ? C11 C12 C13 C14 -175.5(3) . . . . ? C12 C13 C14 C15 -1.3(5) . . . . ? C13 C14 C15 C16 0.2(5) . . . . ? C14 C15 C16 C17 0.1(5) . . . . ? C15 C16 C17 C12 0.7(5) . . . . ? C13 C12 C17 C16 -1.8(4) . . . . ? C11 C12 C17 C16 175.6(3) . . . . ? C3 O3 C18 O2 -176.9(3) . . . . ? C3 O3 C18 C8 3.3(3) . . . . ? C2 C8 C18 O2 178.2(4) . . . . ? C9 C8 C18 O2 -4.6(6) . . . . ? C2 C8 C18 O3 -2.1(3) . . . . ? C9 C8 C18 O3 175.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.925 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.925 _refine_diff_density_max 0.152 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.044 data_compound_3 _database_code_CSD 212059 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H22 O8' _chemical_formula_weight 402.39 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.8818(18) _cell_length_b 8.5242(17) _cell_length_c 13.488(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.36(3) _cell_angle_gamma 90.00 _cell_volume 993.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 210 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25.2 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9696 _exptl_absorpt_correction_T_max 0.9796 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 R-axis-IV _diffrn_measurement_method 'Osillation frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2783 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2686 _reflns_number_gt 2378 _reflns_threshold_expression >2sigma(I) _computing_data_collection raxis _computing_cell_refinement raxis _computing_data_reduction raxis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics texsan _computing_publication_material texsan _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^)+(0.0645P)^2^+0.0886P] 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 0.022(2) _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 -1.6(16) _refine_ls_number_reflns 2686 _refine_ls_number_parameters 263 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1171 _refine_ls_wR_factor_gt 0.1118 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 0.72565(19) 0.9150(2) 1.27682(12) 0.0601(5) Uani 1 1 d . . . O2 O 1.29473(19) 0.8610(2) 1.11951(16) 0.0736(6) Uani 1 1 d . . . O3 O 1.05166(16) 0.94336(18) 1.05968(12) 0.0467(4) Uani 1 1 d . . . O4 O 0.73183(16) 0.89412(17) 0.92631(11) 0.0428(4) Uani 1 1 d . . . O5 O 0.73900(18) 0.70378(17) 1.16935(12) 0.0494(5) Uani 1 1 d . . . O6 O 0.50409(18) 0.7480(2) 0.91143(12) 0.0538(5) Uani 1 1 d . . . O7 O 1.0723(3) 0.9727(3) 1.41317(16) 0.0943(8) Uani 1 1 d . . . O8 O 0.85292(17) 1.09889(16) 1.08279(11) 0.0399(4) Uani 1 1 d . . . C1 C 0.8228(3) 0.8079(3) 1.24436(18) 0.0493(7) Uani 1 1 d . . . H1A H 0.8749 0.7455 1.3034 0.059 Uiso 1 1 calc R . . C2 C 0.9480(3) 0.9014(3) 1.20576(17) 0.0421(6) Uani 1 1 d . . . C3 C 0.9064(2) 0.9427(3) 1.09084(16) 0.0376(6) Uani 1 1 d . . . C4 C 0.7934(2) 0.8311(3) 1.02480(16) 0.0399(6) Uani 1 1 d . . . H4A H 0.8504 0.7355 1.0162 0.048 Uiso 1 1 calc R . . C5 C 0.6664(3) 0.7851(3) 1.07793(17) 0.0417(6) Uani 1 1 d . . . H5A H 0.6121 0.8785 1.0939 0.050 Uiso 1 1 calc R . . C6 C 0.5549(3) 0.6754(3) 1.0095(2) 0.0537(7) Uani 1 1 d . . . H6A H 0.6057 0.5766 1.0027 0.064 Uiso 1 1 calc R . . H6B H 0.4669 0.6545 1.0387 0.064 Uiso 1 1 calc R . . C7 C 0.6172(3) 0.8397(5) 1.3256(2) 0.0929(12) Uani 1 1 d . . . H7A H 0.5519 0.9175 1.3457 0.139 Uiso 1 1 calc R . . H7B H 0.6724 0.7839 1.3846 0.139 Uiso 1 1 calc R . . H7C H 0.5547 0.7675 1.2789 0.139 Uiso 1 1 calc R . . C8 C 1.0980(3) 0.8078(3) 1.2144(2) 0.0588(8) Uani 1 1 d . . . H8A H 1.1684 0.8252 1.2801 0.071 Uiso 1 1 calc R . . H8B H 1.0765 0.6964 1.2061 0.071 Uiso 1 1 calc R . . C9 C 0.8845(3) 1.3418(3) 1.1717(2) 0.0594(8) Uani 1 1 d . . . H9A H 0.8354 1.3716 1.1032 0.089 Uiso 1 1 calc R . . H9B H 0.9823 1.3945 1.1922 0.089 Uiso 1 1 calc R . . H9C H 0.8197 1.3707 1.2166 0.089 Uiso 1 1 calc R . . C10 C 0.9098(3) 1.1693(3) 1.17642(18) 0.0437(6) Uani 1 1 d . . . C11 C 0.6297(3) 0.7809(3) 0.86638(18) 0.0479(6) Uani 1 1 d . . . H11A H 0.6872 0.6839 0.8625 0.057 Uiso 1 1 calc R . . C12 C 0.5686(3) 0.8430(3) 0.76091(18) 0.0484(7) Uani 1 1 d . . . C13 C 0.4389(4) 0.7788(5) 0.6980(2) 0.0946(12) Uani 1 1 d . . . H13A H 0.3863 0.6985 0.7223 0.114 Uiso 1 1 calc R . . C14 C 0.3853(4) 0.8321(6) 0.5990(2) 0.1028(14) Uani 1 1 d . . . H14A H 0.2966 0.7881 0.5580 0.123 Uiso 1 1 calc R . . C15 C 0.4604(4) 0.9471(5) 0.5616(2) 0.0856(11) Uani 1 1 d . . . H15A H 0.4249 0.9815 0.4948 0.103 Uiso 1 1 calc R . . C16 C 0.5877(4) 1.0119(4) 0.6221(2) 0.0844(11) Uani 1 1 d . . . H16A H 0.6397 1.0916 0.5967 0.101 Uiso 1 1 calc R . . C17 C 0.6417(3) 0.9611(4) 0.7216(2) 0.0710(9) Uani 1 1 d . . . H17A H 0.7290 1.0079 0.7623 0.085 Uiso 1 1 calc R . . C18 C 1.1648(3) 0.8687(3) 1.1304(2) 0.0528(7) Uani 1 1 d . . . C19 C 0.9718(3) 1.0657(3) 1.24998(17) 0.0445(7) Uani 1 1 d . . . C20 C 1.0377(3) 1.0881(4) 1.3594(2) 0.0666(9) Uani 1 1 d . . . C21 C 1.0622(5) 1.2502(5) 1.4054(2) 0.1103(14) Uani 1 1 d . . . H21A H 1.1055 1.2419 1.4773 0.166 Uiso 1 1 calc R . . H21B H 0.9649 1.3042 1.3939 0.166 Uiso 1 1 calc R . . H21C H 1.1320 1.3077 1.3741 0.166 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 0.0564(9) 0.0763(12) 0.0529(9) -0.0003(9) 0.0238(8) -0.0029(9) O2 0.0382(9) 0.0813(13) 0.1033(14) -0.0007(12) 0.0203(9) 0.0044(10) O3 0.0377(8) 0.0492(9) 0.0547(9) -0.0003(7) 0.0136(7) -0.0013(7) O4 0.0417(8) 0.0431(8) 0.0420(8) -0.0058(7) 0.0065(6) -0.0056(7) O5 0.0503(9) 0.0386(8) 0.0580(10) 0.0104(7) 0.0097(8) -0.0032(7) O6 0.0402(9) 0.0646(10) 0.0573(10) -0.0040(8) 0.0129(8) -0.0117(8) O7 0.1041(16) 0.1075(17) 0.0547(12) 0.0262(11) -0.0160(11) -0.0096(14) O8 0.0475(8) 0.0312(7) 0.0372(8) 0.0042(7) 0.0020(7) 0.0028(7) C1 0.0470(13) 0.0512(13) 0.0477(13) 0.0181(11) 0.0068(11) 0.0041(11) C2 0.0390(11) 0.0404(12) 0.0431(12) 0.0091(10) 0.0020(10) 0.0041(10) C3 0.0323(11) 0.0355(11) 0.0451(12) 0.0017(10) 0.0093(10) 0.0046(9) C4 0.0347(11) 0.0365(11) 0.0480(13) 0.0012(10) 0.0086(10) 0.0052(9) C5 0.0402(11) 0.0375(11) 0.0483(13) 0.0022(10) 0.0119(10) -0.0020(10) C6 0.0475(13) 0.0530(14) 0.0622(16) -0.0011(12) 0.0161(13) -0.0149(12) C7 0.0739(18) 0.143(3) 0.0700(18) 0.012(2) 0.0347(15) -0.016(2) C8 0.0420(14) 0.0514(14) 0.0787(18) 0.0166(13) 0.0053(13) 0.0115(12) C9 0.0795(18) 0.0403(13) 0.0540(16) -0.0033(12) 0.0062(14) -0.0019(13) C10 0.0468(13) 0.0424(13) 0.0408(13) -0.0079(10) 0.0078(11) -0.0041(11) C11 0.0428(12) 0.0460(12) 0.0546(14) -0.0128(11) 0.0105(11) -0.0076(11) C12 0.0428(12) 0.0544(14) 0.0487(13) -0.0196(11) 0.0123(11) -0.0034(11) C13 0.085(2) 0.146(3) 0.0502(16) -0.023(2) 0.0100(16) -0.051(2) C14 0.0721(19) 0.177(4) 0.0553(19) -0.024(2) 0.0074(16) -0.030(2) C15 0.077(2) 0.132(3) 0.0452(16) -0.0125(19) 0.0083(15) 0.018(2) C16 0.096(2) 0.088(2) 0.060(2) 0.0079(17) 0.0013(18) -0.010(2) C17 0.0736(18) 0.0732(18) 0.0532(17) 0.0086(15) -0.0116(15) -0.0223(16) C18 0.0387(12) 0.0428(13) 0.0741(17) -0.0015(13) 0.0073(12) 0.0016(11) C19 0.0471(13) 0.0511(14) 0.0316(12) 0.0036(11) 0.0015(11) -0.0018(11) C20 0.0658(17) 0.0830(19) 0.0443(15) 0.0074(15) -0.0008(14) -0.0100(16) C21 0.143(3) 0.122(3) 0.0531(19) -0.031(2) -0.003(2) -0.033(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.394(3) . ? O1 C7 1.437(4) . ? O2 C18 1.198(3) . ? O3 C18 1.372(3) . ? O3 C3 1.446(3) . ? O4 C4 1.420(3) . ? O4 C11 1.438(3) . ? O5 C1 1.420(3) . ? O5 C5 1.432(3) . ? O6 C11 1.416(3) . ? O6 C6 1.436(3) . ? O7 C20 1.218(4) . ? O8 C10 1.384(3) . ? O8 C3 1.410(3) . ? C1 C2 1.552(3) . ? C2 C19 1.518(3) . ? C2 C8 1.534(3) . ? C2 C3 1.549(3) . ? C3 C4 1.514(3) . ? C4 C5 1.521(3) . ? C5 C6 1.511(3) . ? C8 C18 1.489(4) . ? C9 C10 1.486(3) . ? C10 C19 1.348(3) . ? C11 C12 1.497(3) . ? C12 C17 1.370(4) . ? C12 C13 1.376(4) . ? C13 C14 1.387(5) . ? C14 C15 1.348(6) . ? C15 C16 1.350(5) . ? C16 C17 1.386(4) . ? C19 C20 1.469(4) . ? C20 C21 1.510(5) . ? 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 O1 C7 112.3(2) . . ? C18 O3 C3 110.81(18) . . ? C4 O4 C11 109.17(17) . . ? C1 O5 C5 111.62(17) . . ? C11 O6 C6 111.69(17) . . ? C10 O8 C3 107.11(16) . . ? O1 C1 O5 111.88(19) . . ? O1 C1 C2 108.21(19) . . ? O5 C1 C2 112.32(19) . . ? C19 C2 C8 114.20(19) . . ? C19 C2 C3 99.37(17) . . ? C8 C2 C3 101.34(19) . . ? C19 C2 C1 112.8(2) . . ? C8 C2 C1 112.62(19) . . ? C3 C2 C1 115.38(18) . . ? O8 C3 O3 106.31(16) . . ? O8 C3 C4 112.49(16) . . ? O3 C3 C4 110.26(18) . . ? O8 C3 C2 106.86(17) . . ? O3 C3 C2 105.62(16) . . ? C4 C3 C2 114.74(19) . . ? O4 C4 C3 111.85(18) . . ? O4 C4 C5 111.79(17) . . ? C3 C4 C5 110.34(18) . . ? O5 C5 C6 109.11(18) . . ? O5 C5 C4 107.15(17) . . ? C6 C5 C4 108.91(19) . . ? O6 C6 C5 108.54(19) . . ? C18 C8 C2 104.6(2) . . ? C19 C10 O8 112.85(19) . . ? C19 C10 C9 135.4(2) . . ? O8 C10 C9 111.75(19) . . ? O6 C11 O4 110.41(18) . . ? O6 C11 C12 109.22(18) . . ? O4 C11 C12 109.9(2) . . ? C17 C12 C13 117.3(3) . . ? C17 C12 C11 121.8(2) . . ? C13 C12 C11 120.9(3) . . ? C12 C13 C14 121.0(4) . . ? C15 C14 C13 120.6(3) . . ? C14 C15 C16 119.3(3) . . ? C15 C16 C17 120.8(3) . . ? C12 C17 C16 121.0(3) . . ? O2 C18 O3 120.8(2) . . ? O2 C18 C8 129.7(2) . . ? O3 C18 C8 109.5(2) . . ? C10 C19 C20 130.9(2) . . ? C10 C19 C2 108.63(19) . . ? C20 C19 C2 120.1(2) . . ? O7 C20 C19 118.7(3) . . ? O7 C20 C21 120.2(3) . . ? C19 C20 C21 121.2(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 C7 O1 C1 O5 62.9(2) . . . . ? C7 O1 C1 C2 -172.86(19) . . . . ? C5 O5 C1 O1 64.4(2) . . . . ? C5 O5 C1 C2 -57.5(2) . . . . ? O1 C1 C2 C19 22.6(2) . . . . ? O5 C1 C2 C19 146.60(18) . . . . ? O1 C1 C2 C8 153.66(19) . . . . ? O5 C1 C2 C8 -82.3(2) . . . . ? O1 C1 C2 C3 -90.6(2) . . . . ? O5 C1 C2 C3 33.3(3) . . . . ? C10 O8 C3 O3 -91.18(19) . . . . ? C10 O8 C3 C4 148.04(19) . . . . ? C10 O8 C3 C2 21.3(2) . . . . ? C18 O3 C3 O8 129.59(18) . . . . ? C18 O3 C3 C4 -108.2(2) . . . . ? C18 O3 C3 C2 16.3(2) . . . . ? C19 C2 C3 O8 -22.1(2) . . . . ? C8 C2 C3 O8 -139.28(17) . . . . ? C1 C2 C3 O8 98.8(2) . . . . ? C19 C2 C3 O3 90.82(19) . . . . ? C8 C2 C3 O3 -26.4(2) . . . . ? C1 C2 C3 O3 -148.33(18) . . . . ? C19 C2 C3 C4 -147.53(19) . . . . ? C8 C2 C3 C4 95.3(2) . . . . ? C1 C2 C3 C4 -26.7(3) . . . . ? C11 O4 C4 C3 178.10(18) . . . . ? C11 O4 C4 C5 -57.6(2) . . . . ? O8 C3 C4 O4 43.5(2) . . . . ? O3 C3 C4 O4 -75.0(2) . . . . ? C2 C3 C4 O4 165.96(17) . . . . ? O8 C3 C4 C5 -81.6(2) . . . . ? O3 C3 C4 C5 159.93(16) . . . . ? C2 C3 C4 C5 40.8(2) . . . . ? C1 O5 C5 C6 -169.1(2) . . . . ? C1 O5 C5 C4 73.1(2) . . . . ? O4 C4 C5 O5 172.13(17) . . . . ? C3 C4 C5 O5 -62.7(2) . . . . ? O4 C4 C5 C6 54.2(2) . . . . ? C3 C4 C5 C6 179.37(18) . . . . ? C11 O6 C6 C5 59.5(3) . . . . ? O5 C5 C6 O6 -169.74(19) . . . . ? C4 C5 C6 O6 -53.1(2) . . . . ? C19 C2 C8 C18 -78.9(3) . . . . ? C3 C2 C8 C18 26.9(2) . . . . ? C1 C2 C8 C18 150.8(2) . . . . ? C3 O8 C10 C19 -11.3(3) . . . . ? C3 O8 C10 C9 169.8(2) . . . . ? C6 O6 C11 O4 -64.1(2) . . . . ? C6 O6 C11 C12 175.0(2) . . . . ? C4 O4 C11 O6 61.7(2) . . . . ? C4 O4 C11 C12 -177.78(18) . . . . ? O6 C11 C12 C17 141.7(2) . . . . ? O4 C11 C12 C17 20.4(3) . . . . ? O6 C11 C12 C13 -40.8(3) . . . . ? O4 C11 C12 C13 -162.1(3) . . . . ? C17 C12 C13 C14 0.0(5) . . . . ? C11 C12 C13 C14 -177.6(3) . . . . ? C12 C13 C14 C15 0.8(6) . . . . ? C13 C14 C15 C16 -0.9(6) . . . . ? C14 C15 C16 C17 0.2(6) . . . . ? C13 C12 C17 C16 -0.7(5) . . . . ? C11 C12 C17 C16 176.8(3) . . . . ? C15 C16 C17 C12 0.6(5) . . . . ? C3 O3 C18 O2 -177.9(2) . . . . ? C3 O3 C18 C8 1.6(3) . . . . ? C2 C8 C18 O2 160.5(3) . . . . ? C2 C8 C18 O3 -18.9(3) . . . . ? O8 C10 C19 C20 -176.8(2) . . . . ? C9 C10 C19 C20 1.7(5) . . . . ? O8 C10 C19 C2 -3.9(3) . . . . ? C9 C10 C19 C2 174.6(3) . . . . ? C8 C2 C19 C10 122.7(2) . . . . ? C3 C2 C19 C10 15.6(2) . . . . ? C1 C2 C19 C10 -107.1(2) . . . . ? C8 C2 C19 C20 -63.5(3) . . . . ? C3 C2 C19 C20 -170.5(2) . . . . ? C1 C2 C19 C20 66.7(3) . . . . ? C10 C19 C20 O7 172.3(3) . . . . ? C2 C19 C20 O7 0.0(4) . . . . ? C10 C19 C20 C21 -7.6(5) . . . . ? C2 C19 C20 C21 -179.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.892 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.892 _refine_diff_density_max 0.180 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.036 data_compound_6 _database_code_CSD 212060 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H19 N O8' _chemical_formula_weight 377.34 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 11.070(2) _cell_length_b 19.530(4) _cell_length_c 8.6828(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1877.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 230 _cell_measurement_theta_min 2 _cell_measurement_theta_max 25.2 _exptl_crystal_description PRISMATIC _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9688 _exptl_absorpt_correction_T_max 0.9791 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 R-axis-IV _diffrn_measurement_method 'Osillation frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4806 _diffrn_reflns_av_R_equivalents 0.0520 _diffrn_reflns_av_sigmaI/netI 0.0823 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2744 _reflns_number_gt 1892 _reflns_threshold_expression >2sigma(I) _computing_data_collection raxis _computing_cell_refinement raxis _computing_data_reduction raxis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics texsan _computing_publication_material texsan _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^)+(0.0580P)^2^+0.0000P] 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 0.0122(16) _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 2.3(18) _refine_ls_number_reflns 2744 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0980 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1232 _refine_ls_wR_factor_gt 0.1098 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 0.4019(3) 0.24886(15) 0.1391(3) 0.0603(8) Uani 1 1 d . . . O2 O 0.5682(3) 0.2075(2) 0.7821(3) 0.0947(12) Uani 1 1 d . . . O3 O 0.6460(2) 0.20555(15) 0.5460(3) 0.0567(8) Uani 1 1 d . . . O4 O 0.7305(2) 0.11676(14) 0.2805(3) 0.0533(8) Uani 1 1 d . . . O5 O 0.4050(2) 0.13830(14) 0.2398(3) 0.0527(7) Uani 1 1 d . . . O6 O 0.6590(3) 0.03803(16) 0.0984(3) 0.0663(9) Uani 1 1 d . . . O7 O 0.6748(2) 0.24959(14) 0.3023(3) 0.0532(8) Uani 1 1 d . . . O8 O 0.6784(3) 0.36725(18) 0.2880(4) 0.0789(10) Uani 1 1 d . . . N1 N 0.6138(3) 0.31767(19) 0.3231(4) 0.0581(9) Uani 1 1 d . . . C1 C 0.3862(4) 0.2092(2) 0.2709(4) 0.0501(11) Uani 1 1 d . . . H1A H 0.3034 0.2154 0.3083 0.060 Uiso 1 1 calc R . . C2 C 0.4745(4) 0.2363(2) 0.3940(4) 0.0461(10) Uani 1 1 d . . . C3 C 0.6040(3) 0.2051(2) 0.3873(4) 0.0457(10) Uani 1 1 d . . . C4 C 0.6095(4) 0.1336(2) 0.3235(4) 0.0480(10) Uani 1 1 d . . . H4A H 0.5838 0.1018 0.4044 0.058 Uiso 1 1 calc R . . C5 C 0.5255(4) 0.1254(2) 0.1875(5) 0.0510(11) Uani 1 1 d . . . H5A H 0.5476 0.1567 0.1040 0.061 Uiso 1 1 calc R . . C6 C 0.5354(4) 0.0512(2) 0.1358(5) 0.0652(13) Uani 1 1 d . . . H6A H 0.5090 0.0209 0.2175 0.078 Uiso 1 1 calc R . . H6B H 0.4847 0.0435 0.0463 0.078 Uiso 1 1 calc R . . C7 C 0.3162(5) 0.2325(3) 0.0184(5) 0.0794(16) Uani 1 1 d . . . H7A H 0.3317 0.2607 -0.0698 0.119 Uiso 1 1 calc R . . H7B H 0.2356 0.2406 0.0549 0.119 Uiso 1 1 calc R . . H7C H 0.3246 0.1851 -0.0096 0.119 Uiso 1 1 calc R . . C8 C 0.4360(4) 0.2201(2) 0.5586(4) 0.0572(12) Uani 1 1 d . . . H8A H 0.3882 0.2573 0.6009 0.069 Uiso 1 1 calc R . . H8B H 0.3883 0.1785 0.5618 0.069 Uiso 1 1 calc R . . C9 C 0.5044(4) 0.3102(2) 0.3719(5) 0.0525(11) Uani 1 1 d . . . C10 C 0.4245(5) 0.3699(3) 0.3950(6) 0.0829(16) Uani 1 1 d . . . H10A H 0.4676 0.4111 0.3696 0.124 Uiso 1 1 calc R . . H10B H 0.3992 0.3717 0.5006 0.124 Uiso 1 1 calc R . . H10C H 0.3550 0.3657 0.3296 0.124 Uiso 1 1 calc R . . C11 C 0.7365(4) 0.0472(2) 0.2253(5) 0.0576(12) Uani 1 1 d . . . H11A H 0.7132 0.0157 0.3081 0.069 Uiso 1 1 calc R . . C12 C 0.8651(4) 0.0334(2) 0.1785(5) 0.0625(13) Uani 1 1 d . . . C13 C 0.9233(5) -0.0239(3) 0.2328(5) 0.0690(13) Uani 1 1 d . . . H13A H 0.8825 -0.0545 0.2963 0.083 Uiso 1 1 calc R . . C14 C 1.0427(6) -0.0363(3) 0.1934(6) 0.0862(17) Uani 1 1 d . . . H14A H 1.0824 -0.0746 0.2320 0.103 Uiso 1 1 calc R . . C15 C 1.1018(6) 0.0078(4) 0.0980(8) 0.110(2) Uani 1 1 d . . . H15A H 1.1826 0.0002 0.0740 0.132 Uiso 1 1 calc R . . C16 C 1.0431(7) 0.0629(4) 0.0373(9) 0.129(3) Uani 1 1 d . . . H16A H 1.0831 0.0916 -0.0313 0.155 Uiso 1 1 calc R . . C17 C 0.9245(6) 0.0766(3) 0.0771(7) 0.1004(19) Uani 1 1 d . . . H17A H 0.8849 0.1145 0.0360 0.120 Uiso 1 1 calc R . . C18 C 0.5505(4) 0.2115(2) 0.6475(5) 0.0618(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.058(2) 0.058(2) 0.0650(16) 0.0052(14) -0.0127(15) 0.0063(16) O2 0.074(3) 0.156(4) 0.0533(19) -0.016(2) -0.0087(17) 0.016(2) O3 0.0370(17) 0.078(2) 0.0552(15) -0.0160(14) -0.0100(13) 0.0091(15) O4 0.0405(18) 0.060(2) 0.0591(16) -0.0088(14) 0.0013(13) 0.0103(14) O5 0.0369(18) 0.0470(19) 0.0740(17) -0.0064(14) 0.0009(14) -0.0023(13) O6 0.058(2) 0.064(2) 0.0764(19) -0.0191(16) -0.0015(16) 0.0084(16) O7 0.0368(16) 0.050(2) 0.0728(17) -0.0080(14) 0.0069(14) -0.0020(13) O8 0.056(2) 0.065(2) 0.115(3) 0.0036(19) 0.0094(19) -0.0196(19) N1 0.046(2) 0.045(2) 0.083(2) -0.0063(19) 0.0027(19) -0.006(2) C1 0.035(2) 0.053(3) 0.063(2) 0.001(2) -0.0036(19) 0.003(2) C2 0.036(2) 0.039(3) 0.063(2) -0.009(2) 0.0053(19) 0.0059(19) C3 0.032(2) 0.057(3) 0.048(2) -0.0040(19) -0.0060(18) 0.003(2) C4 0.038(3) 0.052(3) 0.054(2) -0.0068(19) -0.0003(18) 0.004(2) C5 0.043(3) 0.048(3) 0.062(2) -0.009(2) -0.001(2) -0.002(2) C6 0.060(4) 0.057(4) 0.079(3) -0.015(2) -0.002(2) -0.001(2) C7 0.071(4) 0.093(4) 0.074(3) -0.008(3) -0.022(3) 0.017(3) C8 0.046(3) 0.061(3) 0.065(2) -0.002(2) 0.007(2) 0.000(2) C9 0.033(3) 0.047(3) 0.077(3) 0.000(2) 0.005(2) 0.002(2) C10 0.070(3) 0.049(3) 0.130(4) -0.005(3) 0.014(3) 0.009(3) C11 0.063(3) 0.041(3) 0.069(3) -0.006(2) 0.001(2) 0.010(2) C12 0.065(3) 0.056(3) 0.067(3) -0.001(2) 0.010(2) 0.017(2) C13 0.073(4) 0.073(4) 0.061(2) -0.012(2) 0.001(2) 0.021(3) C14 0.079(5) 0.090(5) 0.089(3) -0.020(3) -0.006(3) 0.034(3) C15 0.058(4) 0.150(7) 0.122(5) -0.016(5) 0.013(4) 0.032(5) C16 0.100(6) 0.130(7) 0.158(6) 0.040(5) 0.057(5) 0.021(5) C17 0.078(4) 0.090(5) 0.133(4) 0.025(4) 0.035(4) 0.025(4) C18 0.049(3) 0.079(4) 0.057(3) -0.013(2) 0.002(2) 0.005(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 C1 1.393(5) . ? O1 C7 1.449(5) . ? O2 C18 1.188(5) . ? O3 C18 1.381(5) . ? O3 C3 1.455(4) . ? O4 C4 1.428(5) . ? O4 C11 1.443(5) . ? O5 C1 1.425(5) . ? O5 C5 1.431(5) . ? O6 C11 1.408(5) . ? O6 C6 1.430(5) . ? O7 C3 1.383(5) . ? O7 N1 1.502(4) . ? O8 N1 1.242(4) . ? N1 C9 1.292(5) . ? C1 C2 1.542(5) . ? C2 C9 1.493(6) . ? C2 C8 1.525(5) . ? C2 C3 1.559(5) . ? C3 C4 1.504(5) . ? C4 C5 1.512(5) . ? C5 C6 1.519(6) . ? C8 C18 1.494(6) . ? C9 C10 1.477(6) . ? C11 C12 1.505(6) . ? C12 C13 1.376(6) . ? C12 C17 1.385(7) . ? C13 C14 1.386(7) . ? C14 C15 1.362(8) . ? C15 C16 1.364(9) . ? C16 C17 1.383(8) . ? 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 O1 C7 112.9(3) . . ? C18 O3 C3 111.1(3) . . ? C4 O4 C11 110.3(3) . . ? C1 O5 C5 111.6(3) . . ? C11 O6 C6 112.5(3) . . ? C3 O7 N1 103.7(3) . . ? O8 N1 C9 135.1(4) . . ? O8 N1 O7 113.7(3) . . ? C9 N1 O7 111.2(3) . . ? O1 C1 O5 111.5(3) . . ? O1 C1 C2 107.4(3) . . ? O5 C1 C2 111.8(3) . . ? C9 C2 C8 112.5(3) . . ? C9 C2 C1 112.6(3) . . ? C8 C2 C1 113.7(3) . . ? C9 C2 C3 99.7(3) . . ? C8 C2 C3 102.2(3) . . ? C1 C2 C3 115.0(3) . . ? O7 C3 O3 108.7(3) . . ? O7 C3 C4 111.3(3) . . ? O3 C3 C4 109.9(3) . . ? O7 C3 C2 107.2(3) . . ? O3 C3 C2 104.9(3) . . ? C4 C3 C2 114.5(3) . . ? O4 C4 C3 110.4(3) . . ? O4 C4 C5 110.4(3) . . ? C3 C4 C5 111.2(3) . . ? O5 C5 C4 107.9(3) . . ? O5 C5 C6 109.2(3) . . ? C4 C5 C6 106.7(3) . . ? O6 C6 C5 108.0(3) . . ? C18 C8 C2 105.7(4) . . ? N1 C9 C10 121.1(4) . . ? N1 C9 C2 111.1(4) . . ? C10 C9 C2 127.8(4) . . ? O6 C11 O4 110.6(3) . . ? O6 C11 C12 110.0(3) . . ? O4 C11 C12 107.5(4) . . ? C13 C12 C17 119.4(5) . . ? C13 C12 C11 119.7(4) . . ? C17 C12 C11 120.8(4) . . ? C12 C13 C14 120.3(5) . . ? C15 C14 C13 119.9(5) . . ? C14 C15 C16 120.3(6) . . ? C15 C16 C17 120.6(6) . . ? C16 C17 C12 119.4(6) . . ? O2 C18 O3 119.7(4) . . ? O2 C18 C8 131.0(4) . . ? O3 C18 C8 109.3(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 C3 O7 N1 O8 163.2(3) . . . . ? C3 O7 N1 C9 -17.7(4) . . . . ? C7 O1 C1 O5 62.3(4) . . . . ? C7 O1 C1 C2 -174.8(3) . . . . ? C5 O5 C1 O1 61.5(4) . . . . ? C5 O5 C1 C2 -58.8(4) . . . . ? O1 C1 C2 C9 26.9(4) . . . . ? O5 C1 C2 C9 149.6(3) . . . . ? O1 C1 C2 C8 156.3(3) . . . . ? O5 C1 C2 C8 -81.0(4) . . . . ? O1 C1 C2 C3 -86.4(4) . . . . ? O5 C1 C2 C3 36.3(4) . . . . ? N1 O7 C3 O3 -86.8(3) . . . . ? N1 O7 C3 C4 151.9(3) . . . . ? N1 O7 C3 C2 26.1(3) . . . . ? C18 O3 C3 O7 133.3(3) . . . . ? C18 O3 C3 C4 -104.6(4) . . . . ? C18 O3 C3 C2 18.9(4) . . . . ? C9 C2 C3 O7 -25.4(4) . . . . ? C8 C2 C3 O7 -141.1(3) . . . . ? C1 C2 C3 O7 95.3(4) . . . . ? C9 C2 C3 O3 90.1(3) . . . . ? C8 C2 C3 O3 -25.6(4) . . . . ? C1 C2 C3 O3 -149.3(3) . . . . ? C9 C2 C3 C4 -149.3(3) . . . . ? C8 C2 C3 C4 95.0(4) . . . . ? C1 C2 C3 C4 -28.7(5) . . . . ? C11 O4 C4 C3 177.6(3) . . . . ? C11 O4 C4 C5 -59.1(4) . . . . ? O7 C3 C4 O4 41.6(4) . . . . ? O3 C3 C4 O4 -78.9(4) . . . . ? C2 C3 C4 O4 163.4(3) . . . . ? O7 C3 C4 C5 -81.2(4) . . . . ? O3 C3 C4 C5 158.2(3) . . . . ? C2 C3 C4 C5 40.5(4) . . . . ? C1 O5 C5 C4 72.0(4) . . . . ? C1 O5 C5 C6 -172.4(3) . . . . ? O4 C4 C5 O5 176.1(3) . . . . ? C3 C4 C5 O5 -61.0(4) . . . . ? O4 C4 C5 C6 58.8(4) . . . . ? C3 C4 C5 C6 -178.3(4) . . . . ? C11 O6 C6 C5 61.0(5) . . . . ? O5 C5 C6 O6 -174.5(3) . . . . ? C4 C5 C6 O6 -58.1(4) . . . . ? C9 C2 C8 C18 -82.5(4) . . . . ? C1 C2 C8 C18 148.1(4) . . . . ? C3 C2 C8 C18 23.5(4) . . . . ? O8 N1 C9 C10 1.4(7) . . . . ? O7 N1 C9 C10 -177.5(4) . . . . ? O8 N1 C9 C2 179.6(4) . . . . ? O7 N1 C9 C2 0.8(4) . . . . ? C8 C2 C9 N1 121.9(4) . . . . ? C1 C2 C9 N1 -108.1(4) . . . . ? C3 C2 C9 N1 14.3(4) . . . . ? C8 C2 C9 C10 -60.0(6) . . . . ? C1 C2 C9 C10 70.0(5) . . . . ? C3 C2 C9 C10 -167.6(4) . . . . ? C6 O6 C11 O4 -60.7(4) . . . . ? C6 O6 C11 C12 -179.3(4) . . . . ? C4 O4 C11 O6 58.5(4) . . . . ? C4 O4 C11 C12 178.6(3) . . . . ? O6 C11 C12 C13 -110.2(4) . . . . ? O4 C11 C12 C13 129.4(4) . . . . ? O6 C11 C12 C17 67.6(6) . . . . ? O4 C11 C12 C17 -52.8(6) . . . . ? C17 C12 C13 C14 3.7(7) . . . . ? C11 C12 C13 C14 -178.5(4) . . . . ? C12 C13 C14 C15 -1.3(7) . . . . ? C13 C14 C15 C16 -2.0(10) . . . . ? C14 C15 C16 C17 2.9(11) . . . . ? C15 C16 C17 C12 -0.5(11) . . . . ? C13 C12 C17 C16 -2.8(9) . . . . ? C11 C12 C17 C16 179.4(6) . . . . ? C3 O3 C18 O2 174.4(5) . . . . ? C3 O3 C18 C8 -3.7(5) . . . . ? C2 C8 C18 O2 168.8(5) . . . . ? C2 C8 C18 O3 -13.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.897 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.897 _refine_diff_density_max 0.141 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.043