# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Ke Wen' _publ_contact_author_email kwen@brain.ecnu.edu.cn _publ_author_name 'Ke Wen' # Attachment '- 1-EA-862803.cif' data_z2 _database_code_depnum_ccdc_archive 'CCDC 862803' #TrackingRef '- 1-EA-862803.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H12 N4 O8,2(C4 H8 O2),2(H2O)' _chemical_formula_sum 'C30 H32 N4 O14' _chemical_formula_weight 672.59 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 Pnn2 _symmetry_space_group_name_Hall 'P 2 -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1/2' _cell_length_a 14.0268(8) _cell_length_b 17.7897(10) _cell_length_c 5.0012(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1247.96(12) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9925 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 28.33 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.368 _exptl_crystal_size_mid 0.324 _exptl_crystal_size_min 0.268 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.651 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.839693 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'Bruker SAINT (SADABS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13766 _diffrn_reflns_av_R_equivalents 0.0191 _diffrn_reflns_av_sigmaI/netI 0.0118 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2168 _reflns_number_gt 2133 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1019P)^2^+1.1336P] 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 1.1(18) _refine_ls_number_reflns 2168 _refine_ls_number_parameters 203 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1649 _refine_ls_wR_factor_gt 0.1639 _refine_ls_goodness_of_fit_ref 1.132 _refine_ls_restrained_S_all 1.131 _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 0.81155(17) -0.19008(14) 0.2366(6) 0.0372(7) Uani 1 1 d . . . O01 O 0.9334(5) -0.0237(4) 0.3892(19) 0.131(2) Uani 1 1 d . . . O02 O 1.0210(6) -0.1131(4) 0.186(2) 0.156(3) Uani 1 1 d . . . C01 C 0.9903(5) -0.1254(3) 0.680(2) 0.094(3) Uani 1 1 d . . . H01A H 0.9292 -0.1497 0.7285 0.113 Uiso 1 1 calc R . . H01B H 1.0388 -0.1654 0.6564 0.113 Uiso 1 1 calc R . . C02 C 0.9772(5) -0.0792(4) 0.396(2) 0.106(3) Uani 1 1 d . . . C03 C 1.0225(13) -0.0703(9) -0.087(3) 0.187(6) Uani 1 1 d . . . H03A H 1.0876 -0.0514 -0.1238 0.224 Uiso 1 1 calc R . . H03B H 0.9787 -0.0267 -0.0795 0.224 Uiso 1 1 calc R . . O2 O 0.69876(16) -0.27651(12) 0.3047(5) 0.0285(5) Uani 1 1 d . . . H2A H 0.7282 -0.2997 0.1840 0.043 Uiso 1 1 calc R . . O3 O 0.73557(16) 0.01196(13) 0.8905(5) 0.0333(7) Uani 1 1 d . . . O4 O 0.50536(16) -0.18514(12) 1.0606(5) 0.0287(6) Uani 1 1 d . . . N1 N 0.71265(19) 0.15135(15) 1.3988(6) 0.0251(6) Uani 1 1 d . . . N2 N 0.60830(19) 0.09266(14) 0.9721(6) 0.0218(6) Uani 1 1 d . . . C1 C 0.4221(2) -0.14977(17) 1.1181(7) 0.0220(7) Uani 1 1 d . . . C2 C 0.5756(2) -0.15083(17) 0.9055(7) 0.0219(7) Uani 1 1 d . . . C3 C 0.6140(2) -0.19379(17) 0.7017(7) 0.0220(6) Uani 1 1 d . . . H3A H 0.5874 -0.2413 0.6576 0.026 Uiso 1 1 calc R . . C4 C 0.6920(2) -0.16621(17) 0.5633(7) 0.0204(6) Uani 1 1 d . . . C5 C 0.7290(2) -0.09600(17) 0.6237(7) 0.0215(6) Uani 1 1 d . . . H5A H 0.7814 -0.0765 0.5254 0.026 Uiso 1 1 calc R . . C6 C 0.6885(2) -0.05460(18) 0.8299(7) 0.0228(7) Uani 1 1 d . . . C7 C 0.6121(2) -0.08140(17) 0.9774(6) 0.0222(6) Uani 1 1 d . . . H7A H 0.5859 -0.0534 1.1215 0.027 Uiso 1 1 calc R . . C8 C 0.7408(2) -0.21127(18) 0.3490(7) 0.0231(7) Uani 1 1 d . . . C9 C 0.6931(2) 0.06552(18) 1.0466(7) 0.0235(7) Uani 1 1 d . . . C10 C 0.7459(2) 0.09310(17) 1.2587(7) 0.0251(7) Uani 1 1 d . . . H10A H 0.8052 0.0708 1.3042 0.030 Uiso 1 1 calc R . . C11 C 0.6288(2) 0.18009(16) 1.3317(5) 0.0238(7) Uani 1 1 d . . . H11A H 0.6034 0.2213 1.4293 0.029 Uiso 1 1 calc R . . O1W O 0.5000(2) 0.00000(16) 0.4916(5) 0.0412(9) Uani 1 2 d SR . . 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 0.0347(12) 0.0320(13) 0.0451(16) -0.0203(12) 0.0186(12) -0.0073(10) O01 0.130(4) 0.108(4) 0.153(7) 0.015(4) 0.015(5) 0.039(4) O02 0.176(6) 0.119(5) 0.172(9) 0.016(5) 0.063(6) 0.045(5) C01 0.078(4) 0.044(3) 0.159(9) -0.006(4) -0.037(5) 0.009(3) C02 0.081(4) 0.062(3) 0.175(10) -0.008(5) 0.020(6) 0.025(3) C03 0.268(18) 0.174(12) 0.118(11) 0.014(10) 0.018(11) 0.039(13) O2 0.0349(12) 0.0219(11) 0.0288(12) -0.0108(10) 0.0100(10) -0.0016(9) O3 0.0267(11) 0.0298(13) 0.0435(17) -0.0205(12) 0.0050(10) -0.0009(9) O4 0.0354(12) 0.0174(11) 0.0332(14) 0.0071(9) 0.0151(11) 0.0066(9) N1 0.0294(13) 0.0224(13) 0.0234(14) -0.0057(11) -0.0058(11) -0.0013(11) N2 0.0294(13) 0.0170(12) 0.0191(13) -0.0015(10) -0.0014(10) -0.0016(10) C1 0.0289(15) 0.0178(14) 0.0193(15) -0.0007(12) 0.0023(12) -0.0012(11) C2 0.0273(14) 0.0175(14) 0.0210(16) 0.0056(12) 0.0046(13) 0.0066(12) C3 0.0255(14) 0.0184(14) 0.0222(15) -0.0027(12) -0.0014(12) 0.0029(11) C4 0.0247(14) 0.0184(15) 0.0181(14) -0.0034(11) -0.0016(12) 0.0055(11) C5 0.0215(13) 0.0220(15) 0.0209(15) -0.0021(12) -0.0013(13) 0.0022(12) C6 0.0236(14) 0.0214(14) 0.0233(16) -0.0050(12) -0.0047(12) 0.0038(11) C7 0.0272(14) 0.0214(14) 0.0179(15) -0.0020(12) 0.0004(12) 0.0106(12) C8 0.0237(14) 0.0233(15) 0.0223(16) -0.0045(13) 0.0021(13) 0.0046(12) C9 0.0274(15) 0.0188(15) 0.0242(16) -0.0053(12) 0.0021(12) -0.0008(12) C10 0.0284(15) 0.0208(15) 0.0259(18) -0.0052(13) -0.0031(13) 0.0008(12) C11 0.0315(15) 0.0166(13) 0.0234(16) -0.0064(12) -0.0025(13) 0.0013(11) O1W 0.0453(19) 0.058(2) 0.0207(19) 0.000 0.000 0.0200(18) _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 C8 1.201(4) . ? O01 C02 1.164(9) . ? O02 C02 1.359(12) . ? O02 C03 1.565(17) . ? C01 C03 1.588(19) 1_556 ? C01 C02 1.649(15) . ? C03 C01 1.588(19) 1_554 ? O2 C8 1.321(4) . ? O3 C9 1.368(4) . ? O3 C6 1.389(4) . ? O4 C1 1.358(4) . ? O4 C2 1.394(4) . ? N1 C11 1.326(4) . ? N1 C10 1.335(4) . ? N2 C1 1.322(4) 2_655 ? N2 C9 1.337(4) . ? C1 N2 1.322(4) 2_655 ? C1 C11 1.393(4) 2_655 ? C2 C3 1.384(5) . ? C2 C7 1.385(5) . ? C3 C4 1.383(5) . ? C4 C5 1.386(4) . ? C4 C8 1.504(4) . ? C5 C6 1.389(4) . ? C6 C7 1.385(5) . ? C9 C10 1.383(5) . ? C11 C1 1.393(4) 2_655 ? 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 C02 O02 C03 117.8(8) . . ? C03 C01 C02 110.7(7) 1_556 . ? O01 C02 O02 126.3(11) . . ? O01 C02 C01 120.5(10) . . ? O02 C02 C01 113.1(6) . . ? O02 C03 C01 109.7(12) . 1_554 ? C9 O3 C6 120.7(2) . . ? C1 O4 C2 121.5(2) . . ? C11 N1 C10 118.4(3) . . ? C1 N2 C9 114.2(3) 2_655 . ? N2 C1 O4 121.1(3) 2_655 . ? N2 C1 C11 123.8(3) 2_655 2_655 ? O4 C1 C11 115.1(3) . 2_655 ? C3 C2 C7 122.7(3) . . ? C3 C2 O4 116.3(3) . . ? C7 C2 O4 120.5(3) . . ? C4 C3 C2 118.7(3) . . ? C3 C4 C5 120.4(3) . . ? C3 C4 C8 121.8(3) . . ? C5 C4 C8 117.7(3) . . ? C4 C5 C6 119.1(3) . . ? C7 C6 C5 122.0(3) . . ? C7 C6 O3 123.0(3) . . ? C5 C6 O3 114.8(3) . . ? C2 C7 C6 117.1(3) . . ? O1 C8 O2 124.5(3) . . ? O1 C8 C4 122.9(3) . . ? O2 C8 C4 112.6(3) . . ? N2 C9 O3 118.7(3) . . ? N2 C9 C10 124.2(3) . . ? O3 C9 C10 116.8(3) . . ? N1 C10 C9 119.4(3) . . ? N1 C11 C1 119.9(3) . 2_655 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.313 _refine_diff_density_min -0.488 _refine_diff_density_rms 0.081 # Attachment '- 1-Methanol-862804.cif' data_z3 _database_code_depnum_ccdc_archive 'CCDC 862804' #TrackingRef '- 1-Methanol-862804.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H12 N4 O8, (H2 O)' _chemical_formula_sum 'C22 H14 N4 O9' _chemical_formula_weight 478.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnn2 _symmetry_space_group_name_Hall 'P 2 -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 17.7028(17) _cell_length_b 13.9075(14) _cell_length_c 5.0090(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1233.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7007 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 492 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9621 _exptl_absorpt_correction_T_max 0.9818 _exptl_absorpt_process_details 'Bruker SAINT (SADABS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13525 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2121 _reflns_number_gt 2037 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1081P)^2^+0.1972P] 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 0.6(16) _refine_ls_number_reflns 2121 _refine_ls_number_parameters 159 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1477 _refine_ls_wR_factor_gt 0.1459 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _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 0.31405(10) -0.01455(16) 0.2797(5) 0.0488(6) Uani 1 1 d . . . O2 O 0.50326(13) -0.23880(13) 0.1526(6) 0.0611(8) Uani 1 1 d . . . O3 O 0.29982(11) 0.29774(15) -0.5279(5) 0.0469(6) Uani 1 1 d . . . O4 O 0.21678(10) 0.17868(13) -0.4689(4) 0.0370(5) Uani 1 1 d . . . H4A H 0.1932 0.2074 -0.5906 0.055 Uiso 1 1 calc R . . N1 N 0.41439(12) -0.11944(15) 0.2156(4) 0.0324(5) Uani 1 1 d . . . N2 N 0.35514(12) -0.22821(14) 0.6312(5) 0.0327(5) Uani 1 1 d . . . C1 C 0.28050(13) 0.22462(17) -0.4185(5) 0.0276(5) Uani 1 1 d . . . C2 C 0.32617(14) 0.17820(17) -0.2040(5) 0.0274(5) Uani 1 1 d . . . C3 C 0.30288(13) 0.09514(19) -0.0740(5) 0.0320(6) Uani 1 1 d . . . H3A H 0.2578 0.0633 -0.1267 0.038 Uiso 1 1 calc R . . C4 C 0.34618(14) 0.05931(18) 0.1331(5) 0.0326(6) Uani 1 1 d . . . C5 C 0.41262(14) 0.10172(19) 0.2132(5) 0.0331(6) Uani 1 1 d . . . H5A H 0.4418 0.0760 0.3554 0.040 Uiso 1 1 calc R . . C6 C 0.43519(15) 0.18408(18) 0.0765(6) 0.0364(7) Uani 1 1 d . . . C7 C 0.39396(14) 0.22280(17) -0.1298(6) 0.0318(6) Uani 1 1 d . . . H7A H 0.4111 0.2787 -0.2203 0.038 Uiso 1 1 calc R . . C8 C 0.35272(13) -0.09443(19) 0.3472(6) 0.0308(6) Uani 1 1 d . . . C9 C 0.32297(14) -0.14754(19) 0.5544(5) 0.0313(6) Uani 1 1 d . . . H9A H 0.2787 -0.1256 0.6428 0.038 Uiso 1 1 calc R . . C10 C 0.41718(16) -0.25686(19) 0.5027(7) 0.0389(7) Uani 1 1 d . . . H10A H 0.4422 -0.3145 0.5533 0.047 Uiso 1 1 calc R . . C11 C 0.44455(15) -0.20158(19) 0.2949(6) 0.0372(7) Uani 1 1 d . . . O1W O 0.5000 0.0000 -0.2628(16) 0.130(2) Uani 1 2 d S . . H1WA H 0.5006 -0.0493 -0.1624 0.156 Uiso 0.50 1 d PR . . H1WB H 0.4994 0.0493 -0.1624 0.156 Uiso 0.50 1 d PR . . 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 0.0244(8) 0.0627(13) 0.0593(15) 0.0386(11) 0.0043(9) 0.0060(8) O2 0.0595(14) 0.0294(9) 0.094(2) -0.0096(11) 0.0525(14) -0.0037(9) O3 0.0414(11) 0.0438(10) 0.0555(14) 0.0243(10) -0.0189(10) -0.0122(9) O4 0.0296(9) 0.0439(10) 0.0373(11) 0.0121(8) -0.0135(8) -0.0051(7) N1 0.0327(11) 0.0400(11) 0.0245(11) 0.0015(9) 0.0068(9) -0.0095(9) N2 0.0305(11) 0.0339(10) 0.0335(12) 0.0020(9) 0.0084(9) 0.0005(8) C1 0.0249(11) 0.0328(12) 0.0251(13) 0.0033(10) -0.0037(10) 0.0001(9) C2 0.0273(11) 0.0318(12) 0.0231(12) -0.0015(9) -0.0035(10) 0.0028(10) C3 0.0183(11) 0.0440(14) 0.0337(15) 0.0076(11) -0.0025(10) -0.0008(9) C4 0.0244(11) 0.0433(13) 0.0300(14) 0.0099(11) 0.0031(10) 0.0020(10) C5 0.0343(13) 0.0405(13) 0.0244(13) 0.0007(10) -0.0056(11) 0.0131(10) C6 0.0374(13) 0.0313(12) 0.0405(17) -0.0044(10) -0.0185(13) 0.0046(10) C7 0.0289(13) 0.0292(12) 0.0371(15) 0.0032(10) -0.0109(11) -0.0010(10) C8 0.0230(11) 0.0407(13) 0.0288(14) 0.0062(11) -0.0034(10) -0.0043(10) C9 0.0268(10) 0.0404(13) 0.0267(13) 0.0096(11) 0.0048(10) 0.0030(10) C10 0.0343(13) 0.0317(12) 0.0506(18) 0.0006(12) 0.0164(13) -0.0001(10) C11 0.0384(14) 0.0271(11) 0.0462(17) -0.0067(11) 0.0184(13) -0.0048(11) O1W 0.150(5) 0.133(4) 0.107(4) 0.000 0.000 0.046(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C8 1.348(3) . ? O1 C4 1.385(3) . ? O2 C11 1.363(3) . ? O2 C6 1.383(3) 2_655 ? O3 C1 1.205(3) . ? O4 C1 1.321(3) . ? O4 H4A 0.8400 . ? N1 C8 1.322(3) . ? N1 C11 1.322(4) . ? N2 C9 1.316(3) . ? N2 C10 1.334(3) . ? C1 C2 1.492(3) . ? C2 C3 1.389(3) . ? C2 C7 1.401(3) . ? C3 C4 1.383(4) . ? C3 H3A 0.9500 . ? C4 C5 1.375(4) . ? C5 C6 1.393(4) . ? C5 H5A 0.9500 . ? C6 C7 1.375(4) . ? C6 O2 1.383(3) 2_655 ? C7 H7A 0.9500 . ? C8 C9 1.378(4) . ? C9 H9A 0.9500 . ? C10 C11 1.382(4) . ? C10 H10A 0.9500 . ? O1W H1WA 0.8500 . ? O1W H1WB 0.8500 . ? 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 C8 O1 C4 122.4(2) . . ? C11 O2 C6 122.4(2) . 2_655 ? C1 O4 H4A 109.5 . . ? C8 N1 C11 114.3(2) . . ? C9 N2 C10 118.0(2) . . ? O3 C1 O4 124.3(2) . . ? O3 C1 C2 122.6(2) . . ? O4 C1 C2 113.0(2) . . ? C3 C2 C7 119.9(2) . . ? C3 C2 C1 122.5(2) . . ? C7 C2 C1 117.6(2) . . ? C4 C3 C2 119.1(2) . . ? C4 C3 H3A 120.4 . . ? C2 C3 H3A 120.4 . . ? C5 C4 C3 122.6(2) . . ? C5 C4 O1 121.0(2) . . ? C3 C4 O1 115.9(2) . . ? C4 C5 C6 117.0(2) . . ? C4 C5 H5A 121.5 . . ? C6 C5 H5A 121.5 . . ? C7 C6 O2 114.2(2) . 2_655 ? C7 C6 C5 122.6(2) . . ? O2 C6 C5 122.9(3) 2_655 . ? C6 C7 C2 118.7(2) . . ? C6 C7 H7A 120.6 . . ? C2 C7 H7A 120.6 . . ? N1 C8 O1 120.7(2) . . ? N1 C8 C9 123.4(2) . . ? O1 C8 C9 115.9(2) . . ? N2 C9 C8 120.8(2) . . ? N2 C9 H9A 119.6 . . ? C8 C9 H9A 119.6 . . ? N2 C10 C11 119.1(2) . . ? N2 C10 H10A 120.5 . . ? C11 C10 H10A 120.5 . . ? N1 C11 O2 118.6(3) . . ? N1 C11 C10 124.4(2) . . ? O2 C11 C10 116.8(2) . . ? H1WA O1W H1WB 107.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 C1 C2 C3 178.5(3) . . . . ? O4 C1 C2 C3 0.1(3) . . . . ? O3 C1 C2 C7 0.1(4) . . . . ? O4 C1 C2 C7 -178.3(2) . . . . ? C7 C2 C3 C4 1.9(4) . . . . ? C1 C2 C3 C4 -176.4(2) . . . . ? C2 C3 C4 C5 -1.3(4) . . . . ? C2 C3 C4 O1 170.5(2) . . . . ? C8 O1 C4 C5 -53.6(4) . . . . ? C8 O1 C4 C3 134.5(3) . . . . ? C3 C4 C5 C6 0.3(4) . . . . ? O1 C4 C5 C6 -171.1(2) . . . . ? C4 C5 C6 C7 0.1(4) . . . . ? C4 C5 C6 O2 173.7(3) . . . 2_655 ? O2 C6 C7 C2 -173.5(3) 2_655 . . . ? C5 C6 C7 C2 0.6(4) . . . . ? C3 C2 C7 C6 -1.6(4) . . . . ? C1 C2 C7 C6 176.8(2) . . . . ? C11 N1 C8 O1 -177.0(3) . . . . ? C11 N1 C8 C9 1.6(4) . . . . ? C4 O1 C8 N1 -20.0(4) . . . . ? C4 O1 C8 C9 161.3(3) . . . . ? C10 N2 C9 C8 0.0(4) . . . . ? N1 C8 C9 N2 -0.6(4) . . . . ? O1 C8 C9 N2 178.1(2) . . . . ? C9 N2 C10 C11 -0.5(4) . . . . ? C8 N1 C11 O2 172.9(2) . . . . ? C8 N1 C11 C10 -2.2(4) . . . . ? C6 O2 C11 N1 47.9(5) 2_655 . . . ? C6 O2 C11 C10 -136.7(3) 2_655 . . . ? N2 C10 C11 N1 1.7(5) . . . . ? N2 C10 C11 O2 -173.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.313 _refine_diff_density_min -0.549 _refine_diff_density_rms 0.057 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 -0.067 149 46 ' ' 2 0.500 0.500 -0.038 149 46 ' ' _platon_squeeze_details ; ; # Attachment '- 1-Pyridine-862805.cif' data_z4 _database_code_depnum_ccdc_archive 'CCDC 862805' #TrackingRef '- 1-Pyridine-862805.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H12 N4 O8, 3(C5 H5 N)' _chemical_formula_sum 'C37 H27 N7 O8' _chemical_formula_weight 697.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.5968(4) _cell_length_b 12.7228(5) _cell_length_c 13.1435(5) _cell_angle_alpha 108.7840(10) _cell_angle_beta 93.2870(10) _cell_angle_gamma 91.0040(10) _cell_volume 1673.67(11) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6673 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 27.93 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9591 _exptl_absorpt_correction_T_max 0.9676 _exptl_absorpt_process_details 'Bruker SAINT (SADABS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19459 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0261 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5852 _reflns_number_gt 4428 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0470P)^2^+1.0414P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5852 _refine_ls_number_parameters 499 _refine_ls_number_restraints 258 _refine_ls_R_factor_all 0.0625 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1195 _refine_ls_wR_factor_gt 0.1043 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.044 _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 0.57251(16) 0.15368(12) -0.02085(12) 0.0468(4) Uani 1 1 d . . . H1A H 0.6067 0.0921 -0.0335 0.070 Uiso 1 1 calc R . . O2 O 0.66855(18) 0.18531(13) 0.14162(13) 0.0536(5) Uani 1 1 d . . . O3 O -0.09699(18) 0.21922(15) 0.30610(15) 0.0615(5) Uani 1 1 d . . . H3A H -0.1216 0.1574 0.3095 0.092 Uiso 1 1 calc R . . O4 O 0.03762(18) 0.21672(13) 0.44244(15) 0.0556(5) Uani 1 1 d . . . O5 O 0.31701(14) 0.48567(12) 0.01171(11) 0.0376(4) Uani 1 1 d . . . O6 O -0.00989(13) 0.57567(13) 0.24086(12) 0.0388(4) Uani 1 1 d . . . O7 O 0.27326(14) 0.58373(13) 0.54196(11) 0.0429(4) Uani 1 1 d . . . O8 O 0.60476(13) 0.58993(11) 0.32856(11) 0.0341(3) Uani 1 1 d . . . N1 N 0.05660(17) 0.66085(15) 0.01575(14) 0.0373(4) Uani 1 1 d . . . N2 N 0.16052(15) 0.53228(13) 0.13363(13) 0.0295(4) Uani 1 1 d . . . N3 N 0.54647(18) 0.76566(14) 0.59227(14) 0.0379(4) Uani 1 1 d . . . N4 N 0.43336(16) 0.58398(13) 0.42921(13) 0.0304(4) Uani 1 1 d . . . C1 C 0.54479(18) 0.50922(16) 0.23816(15) 0.0288(4) Uani 1 1 d . . . C2 C 0.59385(18) 0.40579(16) 0.20699(15) 0.0292(4) Uani 1 1 d . . . H2A H 0.6594 0.3877 0.2502 0.035 Uiso 1 1 calc R . . C3 C 0.54630(19) 0.32749(16) 0.11100(15) 0.0297(4) Uani 1 1 d . . . C4 C 0.45088(19) 0.35486(17) 0.04841(15) 0.0312(5) Uani 1 1 d . . . H4A H 0.4187 0.3022 -0.0176 0.037 Uiso 1 1 calc R . . C5 C 0.40342(18) 0.45980(17) 0.08350(15) 0.0299(4) Uani 1 1 d . . . C6 C 0.44896(19) 0.53926(16) 0.17863(16) 0.0305(5) Uani 1 1 d . . . H6A H 0.4157 0.6114 0.2019 0.037 Uiso 1 1 calc R . . C7 C 0.18736(19) 0.52762(17) 0.45663(15) 0.0319(5) Uani 1 1 d . . . C8 C 0.14243(19) 0.57744(18) 0.38348(16) 0.0335(5) Uani 1 1 d . . . H8A H 0.1760 0.6475 0.3846 0.040 Uiso 1 1 calc R . . C9 C 0.04728(19) 0.52195(17) 0.30892(16) 0.0315(5) Uani 1 1 d . . . C10 C -0.00304(19) 0.42002(17) 0.30467(16) 0.0325(5) Uani 1 1 d . . . H10A H -0.0686 0.3836 0.2521 0.039 Uiso 1 1 calc R . . C11 C 0.04451(19) 0.37151(17) 0.37937(16) 0.0316(5) Uani 1 1 d . . . C12 C 0.13941(18) 0.42609(17) 0.45605(16) 0.0310(5) Uani 1 1 d . . . H12A H 0.1711 0.3938 0.5078 0.037 Uiso 1 1 calc R . . C13 C 0.21293(18) 0.54401(16) 0.04845(15) 0.0295(4) Uani 1 1 d . . . C14 C 0.16319(19) 0.60735(18) -0.01066(16) 0.0341(5) Uani 1 1 d . . . H14A H 0.2052 0.6129 -0.0707 0.041 Uiso 1 1 calc R . . C15 C 0.0023(2) 0.65012(18) 0.10047(17) 0.0348(5) Uani 1 1 d . . . H15A H -0.0736 0.6870 0.1220 0.042 Uiso 1 1 calc R . . C16 C 0.05503(19) 0.58576(16) 0.15796(16) 0.0303(4) Uani 1 1 d . . . C17 C 0.6001(2) 0.72043(17) 0.50046(16) 0.0342(5) Uani 1 1 d . . . H17A H 0.6795 0.7498 0.4898 0.041 Uiso 1 1 calc R . . C18 C 0.54231(19) 0.63094(16) 0.41967(15) 0.0291(4) Uani 1 1 d . . . C19 C 0.38171(19) 0.63023(17) 0.52167(16) 0.0320(5) Uani 1 1 d . . . C20 C 0.4354(2) 0.72120(17) 0.60312(16) 0.0355(5) Uani 1 1 d . . . H20A H 0.3927 0.7521 0.6671 0.043 Uiso 1 1 calc R . . C21 C 0.6020(2) 0.21457(17) 0.07847(16) 0.0353(5) Uani 1 1 d . . . C22 C -0.0049(2) 0.26128(18) 0.37978(19) 0.0399(5) Uani 1 1 d . . . N01 N 0.6467(4) 0.2001(3) 0.6799(4) 0.0575(14) Uani 0.50 1 d PGU A 1 C01 C 0.7268(4) 0.1819(3) 0.7595(2) 0.0337(11) Uani 0.50 1 d PGU A 1 H01A H 0.7436 0.2391 0.8265 0.040 Uiso 0.50 1 calc PR A 1 C02 C 0.7825(4) 0.0798(3) 0.7410(3) 0.0455(14) Uani 0.50 1 d PGU A 1 H02A H 0.8373 0.0673 0.7954 0.055 Uiso 0.50 1 calc PR A 1 C03 C 0.7580(4) -0.0039(2) 0.6429(4) 0.0478(15) Uani 0.50 1 d PGU A 1 H03A H 0.7961 -0.0736 0.6303 0.057 Uiso 0.50 1 calc PR A 1 C04 C 0.6779(5) 0.0144(3) 0.5633(2) 0.0468(15) Uani 0.50 1 d PGU A 1 H04A H 0.6611 -0.0429 0.4963 0.056 Uiso 0.50 1 calc PR A 1 C05 C 0.6222(5) 0.1164(4) 0.5818(3) 0.0681(19) Uani 0.50 1 d PGU A 1 H05A H 0.5674 0.1289 0.5274 0.082 Uiso 0.50 1 calc PR A 1 N01' N 0.6642(5) 0.1947(3) 0.7199(4) 0.0610(14) Uani 0.50 1 d PGU B 2 C01' C 0.7494(5) 0.1482(4) 0.7760(2) 0.0599(17) Uani 0.50 1 d PGU B 2 H01H H 0.7695 0.1841 0.8507 0.072 Uiso 0.50 1 calc PR B 2 C02' C 0.8052(4) 0.0492(4) 0.7227(3) 0.0578(17) Uani 0.50 1 d PGU B 2 H02B H 0.8634 0.0175 0.7611 0.069 Uiso 0.50 1 calc PR B 2 C03' C 0.7758(4) -0.0033(3) 0.6134(3) 0.0492(15) Uani 0.50 1 d PGU B 2 H03B H 0.8140 -0.0710 0.5770 0.059 Uiso 0.50 1 calc PR B 2 C04' C 0.6906(5) 0.0432(4) 0.5573(2) 0.0494(16) Uani 0.50 1 d PGU B 2 H04B H 0.6705 0.0073 0.4825 0.059 Uiso 0.50 1 calc PR B 2 C05' C 0.6348(4) 0.1422(4) 0.6105(4) 0.0569(15) Uani 0.50 1 d PGU B 2 H05B H 0.5766 0.1740 0.5722 0.068 Uiso 0.50 1 calc PR B 2 N02 N 0.1876(2) -0.02232(17) 0.69729(17) 0.0523(5) Uani 1 1 d . . . C06 C 0.1189(3) 0.0413(3) 0.6565(2) 0.0617(7) Uani 1 1 d . . . H06A H 0.0406 0.0119 0.6180 0.074 Uiso 1 1 calc R . . C07 C 0.1557(4) 0.1488(3) 0.6674(2) 0.0735(10) Uani 1 1 d . . . H07A H 0.1037 0.1933 0.6378 0.088 Uiso 1 1 calc R . . C08 C 0.2691(4) 0.1900(2) 0.7222(2) 0.0758(11) Uani 1 1 d . . . H08A H 0.2965 0.2643 0.7319 0.091 Uiso 1 1 calc R . . C09 C 0.3426(3) 0.1240(2) 0.7627(2) 0.0623(8) Uani 1 1 d . . . H09A H 0.4226 0.1503 0.7994 0.075 Uiso 1 1 calc R . . C010 C 0.2975(3) 0.0187(2) 0.7489(2) 0.0533(6) Uani 1 1 d . . . H01B H 0.3476 -0.0273 0.7779 0.064 Uiso 1 1 calc R . . N03 N 0.30247(18) 0.02854(15) 0.06532(14) 0.0407(4) Uani 1 1 d . . . C011 C 0.2046(2) 0.0326(2) -0.00116(19) 0.0485(6) Uani 1 1 d . . . H01C H 0.1834 -0.0303 -0.0627 0.058 Uiso 1 1 calc R . . C012 C 0.1324(3) 0.1259(2) 0.0166(2) 0.0557(7) Uani 1 1 d . . . H01D H 0.0628 0.1270 -0.0319 0.067 Uiso 1 1 calc R . . C013 C 0.1636(2) 0.2166(2) 0.1057(2) 0.0511(6) Uani 1 1 d . . . H01E H 0.1166 0.2820 0.1192 0.061 Uiso 1 1 calc R . . C014 C 0.2634(2) 0.21171(19) 0.1748(2) 0.0478(6) Uani 1 1 d . . . H01F H 0.2861 0.2732 0.2374 0.057 Uiso 1 1 calc R . . C015 C 0.3297(2) 0.11650(19) 0.15197(18) 0.0434(6) Uani 1 1 d . . . H01G H 0.3985 0.1132 0.2003 0.052 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 0.0637(11) 0.0367(8) 0.0324(8) 0.0013(7) -0.0042(8) 0.0158(8) O2 0.0718(12) 0.0480(10) 0.0340(9) 0.0045(7) -0.0082(8) 0.0258(9) O3 0.0629(12) 0.0505(10) 0.0732(13) 0.0278(9) -0.0168(10) -0.0199(9) O4 0.0675(12) 0.0392(9) 0.0650(12) 0.0247(9) -0.0022(9) 0.0056(8) O5 0.0367(8) 0.0516(9) 0.0250(7) 0.0122(7) 0.0055(6) 0.0129(7) O6 0.0329(8) 0.0539(9) 0.0383(8) 0.0252(7) 0.0095(7) 0.0109(7) O7 0.0403(9) 0.0617(10) 0.0231(7) 0.0094(7) 0.0036(6) -0.0129(7) O8 0.0290(7) 0.0361(8) 0.0301(7) 0.0007(6) 0.0039(6) -0.0035(6) N1 0.0346(10) 0.0454(10) 0.0361(10) 0.0197(8) -0.0019(8) 0.0023(8) N2 0.0293(9) 0.0326(9) 0.0261(9) 0.0087(7) 0.0015(7) 0.0021(7) N3 0.0476(11) 0.0339(9) 0.0281(9) 0.0055(8) -0.0027(8) -0.0027(8) N4 0.0325(9) 0.0324(9) 0.0250(9) 0.0076(7) 0.0017(7) -0.0007(7) C1 0.0274(10) 0.0328(10) 0.0237(10) 0.0051(8) 0.0056(8) -0.0029(8) C2 0.0281(10) 0.0355(11) 0.0258(10) 0.0117(9) 0.0065(8) 0.0017(8) C3 0.0322(11) 0.0328(11) 0.0244(10) 0.0085(8) 0.0075(9) 0.0013(8) C4 0.0340(11) 0.0357(11) 0.0217(10) 0.0055(8) 0.0053(8) 0.0002(9) C5 0.0282(10) 0.0398(11) 0.0244(10) 0.0132(9) 0.0072(8) 0.0048(9) C6 0.0312(11) 0.0313(10) 0.0295(10) 0.0090(9) 0.0099(9) 0.0046(8) C7 0.0277(11) 0.0429(12) 0.0222(10) 0.0057(9) 0.0064(8) 0.0013(9) C8 0.0340(11) 0.0388(11) 0.0297(11) 0.0126(9) 0.0092(9) 0.0002(9) C9 0.0270(10) 0.0429(12) 0.0290(10) 0.0162(9) 0.0091(9) 0.0092(9) C10 0.0261(10) 0.0403(12) 0.0295(11) 0.0081(9) 0.0056(8) 0.0048(9) C11 0.0283(11) 0.0332(11) 0.0334(11) 0.0091(9) 0.0093(9) 0.0082(8) C12 0.0272(10) 0.0401(11) 0.0282(10) 0.0129(9) 0.0082(8) 0.0104(9) C13 0.0290(10) 0.0337(10) 0.0239(10) 0.0065(8) 0.0014(8) 0.0015(8) C14 0.0317(11) 0.0444(12) 0.0290(11) 0.0158(9) 0.0009(9) -0.0003(9) C15 0.0293(11) 0.0407(12) 0.0367(12) 0.0155(10) 0.0007(9) 0.0059(9) C16 0.0295(11) 0.0340(11) 0.0271(10) 0.0099(9) 0.0012(8) 0.0000(8) C17 0.0357(12) 0.0318(11) 0.0325(11) 0.0075(9) -0.0010(9) -0.0029(9) C18 0.0302(11) 0.0283(10) 0.0273(10) 0.0072(8) 0.0007(8) 0.0026(8) C19 0.0343(11) 0.0368(11) 0.0252(10) 0.0109(9) 0.0013(9) -0.0006(9) C20 0.0457(13) 0.0366(11) 0.0230(10) 0.0078(9) 0.0018(9) 0.0030(10) C21 0.0404(12) 0.0361(11) 0.0275(11) 0.0069(9) 0.0054(10) 0.0035(9) C22 0.0389(13) 0.0361(12) 0.0453(13) 0.0126(11) 0.0089(11) 0.0068(10) N01 0.064(2) 0.051(2) 0.054(2) 0.0149(16) -0.0066(16) 0.0106(15) C01 0.0339(18) 0.0345(17) 0.0312(17) 0.0105(14) -0.0077(14) 0.0002(15) C02 0.046(2) 0.042(2) 0.049(2) 0.0160(16) -0.0035(16) 0.0048(16) C03 0.051(2) 0.041(2) 0.050(2) 0.0122(15) 0.0061(17) 0.0083(16) C04 0.054(2) 0.044(2) 0.046(2) 0.0181(16) 0.0048(16) -0.0013(16) C05 0.073(3) 0.061(2) 0.068(2) 0.0183(18) -0.0010(18) 0.0072(18) N01' 0.066(2) 0.055(2) 0.058(2) 0.0124(15) 0.0043(17) 0.0085(16) C01' 0.060(2) 0.057(2) 0.061(2) 0.0153(17) 0.0071(17) 0.0051(17) C02' 0.056(2) 0.059(2) 0.056(2) 0.0149(17) 0.0070(17) 0.0046(17) C03' 0.051(2) 0.046(2) 0.050(2) 0.0152(15) 0.0089(17) 0.0021(16) C04' 0.051(2) 0.047(2) 0.048(2) 0.0127(16) 0.0046(16) 0.0004(17) C05' 0.061(2) 0.058(2) 0.051(2) 0.0185(17) -0.0044(16) 0.0089(17) N02 0.0615(14) 0.0433(11) 0.0530(13) 0.0175(10) 0.0028(11) -0.0076(10) C06 0.0591(17) 0.0705(19) 0.0548(16) 0.0191(15) 0.0038(14) 0.0075(15) C07 0.116(3) 0.0624(19) 0.0526(17) 0.0282(15) 0.0236(19) 0.038(2) C08 0.143(3) 0.0341(14) 0.0503(17) 0.0086(13) 0.038(2) -0.0126(18) C09 0.0744(19) 0.0585(17) 0.0451(15) 0.0049(13) 0.0088(14) -0.0213(15) C010 0.0656(18) 0.0493(15) 0.0446(14) 0.0154(12) 0.0002(13) 0.0026(13) N03 0.0464(11) 0.0399(10) 0.0335(10) 0.0083(8) 0.0040(9) 0.0095(8) C011 0.0574(16) 0.0491(14) 0.0337(12) 0.0067(11) -0.0027(11) 0.0057(12) C012 0.0592(17) 0.0597(16) 0.0453(14) 0.0132(13) -0.0025(12) 0.0206(13) C013 0.0582(16) 0.0491(14) 0.0462(14) 0.0130(12) 0.0124(12) 0.0248(12) C014 0.0570(16) 0.0390(13) 0.0420(13) 0.0043(10) 0.0076(12) 0.0069(11) C015 0.0428(13) 0.0434(13) 0.0387(13) 0.0061(10) 0.0009(10) 0.0047(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 C21 1.302(2) . ? O1 H1A 0.8400 . ? O2 C21 1.211(3) . ? O3 C22 1.310(3) . ? O3 H3A 0.8400 . ? O4 C22 1.212(3) . ? O5 C13 1.364(2) . ? O5 C5 1.396(2) . ? O6 C16 1.360(2) . ? O6 C9 1.407(2) . ? O7 C19 1.362(2) . ? O7 C7 1.393(2) . ? O8 C18 1.358(2) . ? O8 C1 1.405(2) . ? N1 C15 1.326(3) . ? N1 C14 1.334(3) . ? N2 C16 1.320(3) . ? N2 C13 1.327(2) . ? N3 C17 1.324(3) . ? N3 C20 1.332(3) . ? N4 C18 1.321(3) . ? N4 C19 1.323(2) . ? C1 C2 1.368(3) . ? C1 C6 1.380(3) . ? C2 C3 1.392(3) . ? C2 H2A 0.9500 . ? C3 C4 1.386(3) . ? C3 C21 1.503(3) . ? C4 C5 1.379(3) . ? C4 H4A 0.9500 . ? C5 C6 1.385(3) . ? C6 H6A 0.9500 . ? C7 C12 1.377(3) . ? C7 C8 1.380(3) . ? C8 C9 1.375(3) . ? C8 H8A 0.9500 . ? C9 C10 1.377(3) . ? C10 C11 1.394(3) . ? C10 H10A 0.9500 . ? C11 C12 1.385(3) . ? C11 C22 1.490(3) . ? C12 H12A 0.9500 . ? C13 C14 1.379(3) . ? C14 H14A 0.9500 . ? C15 C16 1.385(3) . ? C15 H15A 0.9500 . ? C17 C18 1.386(3) . ? C17 H17A 0.9500 . ? C19 C20 1.385(3) . ? C20 H20A 0.9500 . ? N01 C01 1.3900 . ? N01 C05 1.3900 . ? C01 C02 1.3900 . ? C01 H01A 0.9500 . ? C02 C03 1.3900 . ? C02 H02A 0.9500 . ? C03 C04 1.3900 . ? C03 H03A 0.9500 . ? C04 C05 1.3900 . ? C04 H04A 0.9500 . ? C05 H05A 0.9500 . ? N01' C01' 1.3900 . ? N01' C05' 1.3900 . ? C01' C02' 1.3900 . ? C01' H01H 0.9500 . ? C02' C03' 1.3900 . ? C02' H02B 0.9500 . ? C03' C04' 1.3900 . ? C03' H03B 0.9500 . ? C04' C05' 1.3900 . ? C04' H04B 0.9500 . ? C05' H05B 0.9500 . ? N02 C06 1.314(4) . ? N02 C010 1.323(3) . ? C06 C07 1.376(4) . ? C06 H06A 0.9500 . ? C07 C08 1.368(5) . ? C07 H07A 0.9500 . ? C08 C09 1.364(5) . ? C08 H08A 0.9500 . ? C09 C010 1.366(4) . ? C09 H09A 0.9500 . ? C010 H01B 0.9500 . ? N03 C015 1.328(3) . ? N03 C011 1.330(3) . ? C011 C012 1.386(3) . ? C011 H01C 0.9500 . ? C012 C013 1.372(4) . ? C012 H01D 0.9500 . ? C013 C014 1.370(3) . ? C013 H01E 0.9500 . ? C014 C015 1.368(3) . ? C014 H01F 0.9500 . ? C015 H01G 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C21 O1 H1A 109.5 . . ? C22 O3 H3A 109.5 . . ? C13 O5 C5 120.18(15) . . ? C16 O6 C9 118.49(15) . . ? C19 O7 C7 119.46(15) . . ? C18 O8 C1 119.85(15) . . ? C15 N1 C14 116.97(18) . . ? C16 N2 C13 114.74(17) . . ? C17 N3 C20 117.03(18) . . ? C18 N4 C19 114.81(17) . . ? C2 C1 C6 122.66(18) . . ? C2 C1 O8 117.38(18) . . ? C6 C1 O8 119.62(17) . . ? C1 C2 C3 118.99(19) . . ? C1 C2 H2A 120.5 . . ? C3 C2 H2A 120.5 . . ? C4 C3 C2 120.06(18) . . ? C4 C3 C21 121.99(18) . . ? C2 C3 C21 117.95(18) . . ? C5 C4 C3 118.96(18) . . ? C5 C4 H4A 120.5 . . ? C3 C4 H4A 120.5 . . ? C4 C5 C6 122.17(19) . . ? C4 C5 O5 115.97(17) . . ? C6 C5 O5 121.47(18) . . ? C1 C6 C5 117.15(18) . . ? C1 C6 H6A 121.4 . . ? C5 C6 H6A 121.4 . . ? C12 C7 C8 121.80(19) . . ? C12 C7 O7 116.79(18) . . ? C8 C7 O7 121.03(19) . . ? C9 C8 C7 117.60(19) . . ? C9 C8 H8A 121.2 . . ? C7 C8 H8A 121.2 . . ? C8 C9 C10 122.72(19) . . ? C8 C9 O6 118.92(19) . . ? C10 C9 O6 118.06(18) . . ? C9 C10 C11 118.41(19) . . ? C9 C10 H10A 120.8 . . ? C11 C10 H10A 120.8 . . ? C12 C11 C10 120.08(19) . . ? C12 C11 C22 118.35(19) . . ? C10 C11 C22 121.57(19) . . ? C7 C12 C11 119.38(19) . . ? C7 C12 H12A 120.3 . . ? C11 C12 H12A 120.3 . . ? N2 C13 O5 119.41(18) . . ? N2 C13 C14 123.49(19) . . ? O5 C13 C14 116.96(18) . . ? N1 C14 C13 120.61(19) . . ? N1 C14 H14A 119.7 . . ? C13 C14 H14A 119.7 . . ? N1 C15 C16 120.83(19) . . ? N1 C15 H15A 119.6 . . ? C16 C15 H15A 119.6 . . ? N2 C16 O6 119.82(18) . . ? N2 C16 C15 123.35(19) . . ? O6 C16 C15 116.78(18) . . ? N3 C17 C18 121.05(19) . . ? N3 C17 H17A 119.5 . . ? C18 C17 H17A 119.5 . . ? N4 C18 O8 120.07(17) . . ? N4 C18 C17 123.11(18) . . ? O8 C18 C17 116.79(18) . . ? N4 C19 O7 119.26(17) . . ? N4 C19 C20 123.61(19) . . ? O7 C19 C20 117.04(18) . . ? N3 C20 C19 120.38(19) . . ? N3 C20 H20A 119.8 . . ? C19 C20 H20A 119.8 . . ? O2 C21 O1 124.4(2) . . ? O2 C21 C3 121.09(18) . . ? O1 C21 C3 114.55(19) . . ? O4 C22 O3 124.7(2) . . ? O4 C22 C11 122.4(2) . . ? O3 C22 C11 113.0(2) . . ? C01 N01 C05 120.0 . . ? C02 C01 N01 120.0 . . ? C02 C01 H01A 120.0 . . ? N01 C01 H01A 120.0 . . ? C01 C02 C03 120.0 . . ? C01 C02 H02A 120.0 . . ? C03 C02 H02A 120.0 . . ? C04 C03 C02 120.0 . . ? C04 C03 H03A 120.0 . . ? C02 C03 H03A 120.0 . . ? C03 C04 C05 120.0 . . ? C03 C04 H04A 120.0 . . ? C05 C04 H04A 120.0 . . ? C04 C05 N01 120.0 . . ? C04 C05 H05A 120.0 . . ? N01 C05 H05A 120.0 . . ? C01' N01' C05' 120.0 . . ? N01' C01' C02' 120.0 . . ? N01' C01' H01H 120.0 . . ? C02' C01' H01H 120.0 . . ? C01' C02' C03' 120.0 . . ? C01' C02' H02B 120.0 . . ? C03' C02' H02B 120.0 . . ? C04' C03' C02' 120.0 . . ? C04' C03' H03B 120.0 . . ? C02' C03' H03B 120.0 . . ? C03' C04' C05' 120.0 . . ? C03' C04' H04B 120.0 . . ? C05' C04' H04B 120.0 . . ? C04' C05' N01' 120.0 . . ? C04' C05' H05B 120.0 . . ? N01' C05' H05B 120.0 . . ? C06 N02 C010 118.2(2) . . ? N02 C06 C07 122.6(3) . . ? N02 C06 H06A 118.7 . . ? C07 C06 H06A 118.7 . . ? C08 C07 C06 118.2(3) . . ? C08 C07 H07A 120.9 . . ? C06 C07 H07A 120.9 . . ? C09 C08 C07 119.7(3) . . ? C09 C08 H08A 120.1 . . ? C07 C08 H08A 120.1 . . ? C08 C09 C010 117.9(3) . . ? C08 C09 H09A 121.0 . . ? C010 C09 H09A 121.0 . . ? N02 C010 C09 123.3(3) . . ? N02 C010 H01B 118.3 . . ? C09 C010 H01B 118.3 . . ? C015 N03 C011 118.3(2) . . ? N03 C011 C012 122.1(2) . . ? N03 C011 H01C 119.0 . . ? C012 C011 H01C 119.0 . . ? C013 C012 C011 118.6(2) . . ? C013 C012 H01D 120.7 . . ? C011 C012 H01D 120.7 . . ? C014 C013 C012 119.2(2) . . ? C014 C013 H01E 120.4 . . ? C012 C013 H01E 120.4 . . ? C015 C014 C013 118.7(2) . . ? C015 C014 H01F 120.7 . . ? C013 C014 H01F 120.7 . . ? N03 C015 C014 123.1(2) . . ? N03 C015 H01G 118.5 . . ? C014 C015 H01G 118.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C18 O8 C1 C2 -114.4(2) . . . . ? C18 O8 C1 C6 72.1(2) . . . . ? C6 C1 C2 C3 0.5(3) . . . . ? O8 C1 C2 C3 -172.74(16) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C1 C2 C3 C21 179.88(18) . . . . ? C2 C3 C4 C5 -0.8(3) . . . . ? C21 C3 C4 C5 179.51(18) . . . . ? C3 C4 C5 C6 0.8(3) . . . . ? C3 C4 C5 O5 173.66(17) . . . . ? C13 O5 C5 C4 139.55(18) . . . . ? C13 O5 C5 C6 -47.5(3) . . . . ? C2 C1 C6 C5 -0.5(3) . . . . ? O8 C1 C6 C5 172.59(17) . . . . ? C4 C5 C6 C1 -0.1(3) . . . . ? O5 C5 C6 C1 -172.65(17) . . . . ? C19 O7 C7 C12 134.16(19) . . . . ? C19 O7 C7 C8 -52.9(3) . . . . ? C12 C7 C8 C9 -0.1(3) . . . . ? O7 C7 C8 C9 -172.71(17) . . . . ? C7 C8 C9 C10 -0.4(3) . . . . ? C7 C8 C9 O6 173.22(17) . . . . ? C16 O6 C9 C8 75.2(2) . . . . ? C16 O6 C9 C10 -111.0(2) . . . . ? C8 C9 C10 C11 0.2(3) . . . . ? O6 C9 C10 C11 -173.48(17) . . . . ? C9 C10 C11 C12 0.5(3) . . . . ? C9 C10 C11 C22 -179.89(18) . . . . ? C8 C7 C12 C11 0.8(3) . . . . ? O7 C7 C12 C11 173.68(17) . . . . ? C10 C11 C12 C7 -1.0(3) . . . . ? C22 C11 C12 C7 179.43(18) . . . . ? C16 N2 C13 O5 -175.20(17) . . . . ? C16 N2 C13 C14 0.5(3) . . . . ? C5 O5 C13 N2 -31.5(3) . . . . ? C5 O5 C13 C14 152.52(18) . . . . ? C15 N1 C14 C13 0.1(3) . . . . ? N2 C13 C14 N1 -0.3(3) . . . . ? O5 C13 C14 N1 175.44(18) . . . . ? C14 N1 C15 C16 -0.1(3) . . . . ? C13 N2 C16 O6 177.08(17) . . . . ? C13 N2 C16 C15 -0.5(3) . . . . ? C9 O6 C16 N2 9.6(3) . . . . ? C9 O6 C16 C15 -172.73(18) . . . . ? N1 C15 C16 N2 0.3(3) . . . . ? N1 C15 C16 O6 -177.29(18) . . . . ? C20 N3 C17 C18 0.1(3) . . . . ? C19 N4 C18 O8 179.40(18) . . . . ? C19 N4 C18 C17 1.2(3) . . . . ? C1 O8 C18 N4 10.0(3) . . . . ? C1 O8 C18 C17 -171.66(18) . . . . ? N3 C17 C18 N4 -1.5(3) . . . . ? N3 C17 C18 O8 -179.77(19) . . . . ? C18 N4 C19 O7 -176.02(18) . . . . ? C18 N4 C19 C20 0.4(3) . . . . ? C7 O7 C19 N4 -30.6(3) . . . . ? C7 O7 C19 C20 152.83(19) . . . . ? C17 N3 C20 C19 1.3(3) . . . . ? N4 C19 C20 N3 -1.7(3) . . . . ? O7 C19 C20 N3 174.80(19) . . . . ? C4 C3 C21 O2 -166.9(2) . . . . ? C2 C3 C21 O2 13.3(3) . . . . ? C4 C3 C21 O1 13.1(3) . . . . ? C2 C3 C21 O1 -166.64(18) . . . . ? C12 C11 C22 O4 -2.3(3) . . . . ? C10 C11 C22 O4 178.1(2) . . . . ? C12 C11 C22 O3 177.93(18) . . . . ? C10 C11 C22 O3 -1.7(3) . . . . ? C05 N01 C01 C02 0.0 . . . . ? N01 C01 C02 C03 0.0 . . . . ? C01 C02 C03 C04 0.0 . . . . ? C02 C03 C04 C05 0.0 . . . . ? C03 C04 C05 N01 0.0 . . . . ? C01 N01 C05 C04 0.0 . . . . ? C05' N01' C01' C02' 0.0 . . . . ? N01' C01' C02' C03' 0.0 . . . . ? C01' C02' C03' C04' 0.0 . . . . ? C02' C03' C04' C05' 0.0 . . . . ? C03' C04' C05' N01' 0.0 . . . . ? C01' N01' C05' C04' 0.0 . . . . ? C010 N02 C06 C07 -1.3(4) . . . . ? N02 C06 C07 C08 0.6(4) . . . . ? C06 C07 C08 C09 0.9(4) . . . . ? C07 C08 C09 C010 -1.6(4) . . . . ? C06 N02 C010 C09 0.5(4) . . . . ? C08 C09 C010 N02 0.9(4) . . . . ? C015 N03 C011 C012 1.0(4) . . . . ? N03 C011 C012 C013 0.1(4) . . . . ? C011 C012 C013 C014 -0.9(4) . . . . ? C012 C013 C014 C015 0.7(4) . . . . ? C011 N03 C015 C014 -1.3(4) . . . . ? C013 C014 C015 N03 0.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.342 _refine_diff_density_min -0.408 _refine_diff_density_rms 0.039 data_z1 _database_code_depnum_ccdc_archive 'CCDC 862806' #TrackingRef '- 1-DMSO-862806.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H12 N4 O8, 2(C2 H6 O1 S1)' _chemical_formula_sum 'C26 H24 N4 O10 S2' _chemical_formula_weight 616.61 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.1363(18) _cell_length_b 14.3111(11) _cell_length_c 15.8025(12) _cell_angle_alpha 90.00 _cell_angle_beta 94.313(2) _cell_angle_gamma 90.00 _cell_volume 5668.5(7) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9961 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 26.70 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2560 _exptl_absorpt_coefficient_mu 0.251 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8762 _exptl_absorpt_correction_T_max 0.9194 _exptl_absorpt_process_details 'Bruker SAINT (SADABS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 32387 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4983 _reflns_number_gt 3879 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0415P)^2^+10.9863P] 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 4983 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1221 _refine_ls_wR_factor_gt 0.1077 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.80175(9) 0.32946(16) 0.22508(14) 0.0765(7) Uani 1 1 d . . . H1A H 0.8067 0.3120 0.1769 0.115 Uiso 1 1 calc R . . O2 O 0.86455(10) 0.43131(17) 0.19964(13) 0.0806(7) Uani 1 1 d . . . O3 O 0.97526(9) 0.01386(14) 0.64684(16) 0.0738(6) Uani 1 1 d . . . O4 O 1.04032(9) 0.09502(14) 0.59310(16) 0.0760(7) Uani 1 1 d . . . H4A H 1.0526 0.0429 0.5854 0.114 Uiso 1 1 calc R . . O5 O 0.74650(7) 0.39872(19) 0.51172(12) 0.0719(7) Uani 1 1 d . . . O6 O 0.85138(7) 0.27043(14) 0.73563(12) 0.0574(5) Uani 1 1 d . . . O7 O 1.00557(7) 0.42424(12) 0.63610(12) 0.0507(5) Uani 1 1 d . . . O8 O 0.88912(7) 0.61434(12) 0.47226(11) 0.0502(5) Uani 1 1 d . . . N1 N 0.72718(9) 0.39005(17) 0.73353(15) 0.0560(6) Uani 1 1 d . . . N2 N 0.80219(8) 0.33761(16) 0.62117(14) 0.0488(5) Uani 1 1 d . . . N3 N 0.94402(8) 0.51448(14) 0.55480(12) 0.0387(5) Uani 1 1 d . . . N4 N 0.99424(10) 0.67213(16) 0.62654(16) 0.0578(6) Uani 1 1 d . . . C1 C 0.83294(11) 0.39995(18) 0.24522(17) 0.0479(6) Uani 1 1 d . . . C2 C 0.82663(10) 0.43666(17) 0.33252(15) 0.0403(6) Uani 1 1 d . . . C3 C 0.78916(10) 0.39967(19) 0.38360(16) 0.0452(6) Uani 1 1 d . . . H3A H 0.7657 0.3532 0.3631 0.054 Uiso 1 1 calc R . . C4 C 0.78732(10) 0.4329(2) 0.46501(16) 0.0487(7) Uani 1 1 d . . . C5 C 0.82099(10) 0.5023(2) 0.49696(16) 0.0502(7) Uani 1 1 d . . . H5A H 0.8192 0.5241 0.5521 0.060 Uiso 1 1 calc R . . C6 C 0.85736(10) 0.53849(17) 0.44497(16) 0.0424(6) Uani 1 1 d . . . C7 C 0.86081(10) 0.50687(17) 0.36316(15) 0.0411(6) Uani 1 1 d . . . H7A H 0.8857 0.5323 0.3291 0.049 Uiso 1 1 calc R . . C8 C 0.99492(11) 0.08718(19) 0.62887(18) 0.0513(7) Uani 1 1 d . . . C9 C 0.97030(10) 0.17990(17) 0.64527(16) 0.0429(6) Uani 1 1 d . . . C10 C 0.92045(10) 0.18336(18) 0.67803(16) 0.0462(6) Uani 1 1 d . . . H10A H 0.9024 0.1287 0.6896 0.055 Uiso 1 1 calc R . . C11 C 0.89849(10) 0.26912(19) 0.69292(16) 0.0437(6) Uani 1 1 d . . . C12 C 0.92355(10) 0.35206(18) 0.67576(15) 0.0420(6) Uani 1 1 d . . . H12A H 0.9075 0.4094 0.6845 0.050 Uiso 1 1 calc R . . C13 C 0.97351(9) 0.34637(17) 0.64506(15) 0.0389(5) Uani 1 1 d . . . C14 C 0.99690(10) 0.26208(17) 0.62929(16) 0.0423(6) Uani 1 1 d . . . H14A H 1.0304 0.2602 0.6080 0.051 Uiso 1 1 calc R . . C15 C 0.75754(10) 0.3824(2) 0.59661(17) 0.0491(7) Uani 1 1 d . . . C16 C 0.71975(11) 0.4084(2) 0.65072(19) 0.0535(7) Uani 1 1 d . . . H16A H 0.6889 0.4388 0.6295 0.064 Uiso 1 1 calc R . . C17 C 0.77153(10) 0.34600(19) 0.75960(17) 0.0482(6) Uani 1 1 d . . . H17A H 0.7782 0.3323 0.8170 0.058 Uiso 1 1 calc R . . C18 C 0.80841(9) 0.31973(18) 0.70321(17) 0.0430(6) Uani 1 1 d . . . C19 C 0.95377(12) 0.67946(19) 0.56855(18) 0.0524(7) Uani 1 1 d . . . H19A H 0.9417 0.7382 0.5510 0.063 Uiso 1 1 calc R . . C20 C 0.92924(10) 0.60006(17) 0.53375(15) 0.0399(6) Uani 1 1 d . . . C21 C 0.98439(9) 0.50949(17) 0.61319(15) 0.0389(5) Uani 1 1 d . . . C22 C 1.00969(11) 0.58616(19) 0.64964(17) 0.0489(6) Uani 1 1 d . . . H22A H 1.0378 0.5780 0.6907 0.059 Uiso 1 1 calc R . . S01 S 0.93660(3) 0.85208(5) 0.90425(5) 0.0530(2) Uani 1 1 d . . . O01 O 0.90836(8) 0.94197(14) 0.92439(16) 0.0697(6) Uani 1 1 d . . . C02 C 0.89313(13) 0.7633(2) 0.9379(2) 0.0638(8) Uani 1 1 d . . . H02A H 0.8948 0.7618 0.9988 0.096 Uiso 1 1 calc R . . H02B H 0.9039 0.7038 0.9170 0.096 Uiso 1 1 calc R . . H02C H 0.8572 0.7765 0.9161 0.096 Uiso 1 1 calc R . . C01 C 0.92541(13) 0.8391(2) 0.7927(2) 0.0681(9) Uani 1 1 d . . . H01A H 0.9467 0.8836 0.7649 0.102 Uiso 1 1 calc R . . H01B H 0.8884 0.8497 0.7761 0.102 Uiso 1 1 calc R . . H01C H 0.9351 0.7770 0.7768 0.102 Uiso 1 1 calc R . . S02 S 0.80469(5) 0.14984(11) 0.05271(11) 0.0438(4) Uani 0.50 1 d P A 1 O02 O 0.8301(3) 0.2401(6) 0.0953(5) 0.071(2) Uani 0.50 1 d P A 1 C03 C 0.8528(9) 0.0670(16) 0.0875(16) 0.085(6) Uani 0.50 1 d P A 1 H03A H 0.8509 0.0561 0.1471 0.128 Uiso 0.50 1 calc PR A 1 H03B H 0.8877 0.0900 0.0773 0.128 Uiso 0.50 1 calc PR A 1 H03C H 0.8463 0.0096 0.0570 0.128 Uiso 0.50 1 calc PR A 1 C04 C 0.8231(8) 0.1593(14) -0.0584(8) 0.085(7) Uani 0.50 1 d P A 1 H04A H 0.7988 0.2008 -0.0894 0.127 Uiso 0.50 1 calc PR A 1 H04B H 0.8213 0.0986 -0.0845 0.127 Uiso 0.50 1 calc PR A 1 H04C H 0.8587 0.1832 -0.0589 0.127 Uiso 0.50 1 calc PR A 1 S02' S 0.83780(17) 0.1747(2) 0.05203(17) 0.1238(10) Uani 0.50 1 d P B 2 O02' O 0.8027(3) 0.2392(7) 0.0824(6) 0.086(2) Uani 0.50 1 d P B 2 C03' C 0.8408(10) 0.0646(18) 0.0847(18) 0.121(9) Uani 0.50 1 d P B 2 H03D H 0.8480 0.0630 0.1453 0.182 Uiso 0.50 1 calc PR B 2 H03E H 0.8689 0.0328 0.0584 0.182 Uiso 0.50 1 calc PR B 2 H03F H 0.8074 0.0342 0.0695 0.182 Uiso 0.50 1 calc PR B 2 C04' C 0.8244(9) 0.1638(18) -0.0510(12) 0.112(9) Uani 0.50 1 d P B 2 H04D H 0.8209 0.2246 -0.0765 0.168 Uiso 0.50 1 calc PR B 2 H04E H 0.7916 0.1300 -0.0618 0.168 Uiso 0.50 1 calc PR B 2 H04F H 0.8528 0.1303 -0.0749 0.168 Uiso 0.50 1 calc PR B 2 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 0.0918(16) 0.0720(15) 0.0690(14) -0.0296(12) 0.0282(12) -0.0323(13) O2 0.1120(19) 0.0820(16) 0.0516(12) -0.0138(11) 0.0299(13) -0.0422(14) O3 0.0710(14) 0.0419(12) 0.1102(19) 0.0082(12) 0.0183(13) 0.0027(10) O4 0.0707(14) 0.0431(11) 0.1188(19) 0.0062(12) 0.0385(13) 0.0142(10) O5 0.0387(10) 0.130(2) 0.0466(11) 0.0171(12) 0.0009(9) -0.0164(11) O6 0.0450(10) 0.0675(13) 0.0620(12) 0.0224(10) 0.0188(9) 0.0093(9) O7 0.0374(9) 0.0399(10) 0.0741(13) 0.0074(9) 0.0006(9) -0.0005(8) O8 0.0599(11) 0.0403(10) 0.0485(10) 0.0013(8) -0.0081(9) 0.0010(8) N1 0.0477(13) 0.0620(15) 0.0606(15) 0.0050(12) 0.0202(11) 0.0037(11) N2 0.0378(12) 0.0639(15) 0.0460(13) -0.0014(11) 0.0109(10) -0.0030(10) N3 0.0408(11) 0.0366(11) 0.0391(11) -0.0015(9) 0.0044(9) 0.0002(9) N4 0.0666(16) 0.0423(14) 0.0631(15) -0.0072(11) -0.0051(13) -0.0056(11) C1 0.0574(16) 0.0395(14) 0.0470(15) -0.0005(12) 0.0059(13) -0.0042(12) C2 0.0439(13) 0.0369(13) 0.0397(13) 0.0035(10) 0.0005(11) 0.0044(11) C3 0.0382(13) 0.0482(15) 0.0482(15) 0.0052(12) -0.0027(11) -0.0018(11) C4 0.0351(13) 0.0699(18) 0.0412(14) 0.0100(13) 0.0031(11) -0.0012(12) C5 0.0457(15) 0.0671(18) 0.0377(14) -0.0015(13) 0.0018(12) 0.0027(13) C6 0.0439(14) 0.0404(14) 0.0419(14) 0.0013(11) -0.0045(11) 0.0042(11) C7 0.0441(14) 0.0371(13) 0.0423(14) 0.0070(11) 0.0050(11) 0.0026(11) C8 0.0507(16) 0.0421(15) 0.0610(17) 0.0045(13) 0.0026(13) 0.0058(12) C9 0.0432(14) 0.0396(14) 0.0453(14) 0.0033(11) 0.0000(11) 0.0041(11) C10 0.0439(14) 0.0439(15) 0.0507(15) 0.0081(12) 0.0026(12) -0.0038(11) C11 0.0374(13) 0.0527(16) 0.0416(14) 0.0069(12) 0.0068(11) 0.0030(11) C12 0.0432(14) 0.0420(14) 0.0411(13) 0.0008(11) 0.0045(11) 0.0058(11) C13 0.0372(12) 0.0386(13) 0.0405(13) 0.0035(11) 0.0005(10) -0.0009(10) C14 0.0370(13) 0.0455(14) 0.0446(14) 0.0031(11) 0.0035(11) 0.0050(11) C15 0.0358(14) 0.0650(18) 0.0469(15) 0.0060(13) 0.0065(11) -0.0109(12) C16 0.0382(14) 0.0604(18) 0.0630(18) 0.0116(14) 0.0119(13) -0.0006(12) C17 0.0474(15) 0.0538(16) 0.0450(14) 0.0048(12) 0.0144(12) -0.0053(12) C18 0.0354(13) 0.0435(14) 0.0512(15) 0.0051(12) 0.0112(11) -0.0045(11) C19 0.0653(18) 0.0356(14) 0.0552(17) -0.0039(12) -0.0025(14) 0.0008(12) C20 0.0430(13) 0.0403(14) 0.0368(13) -0.0025(11) 0.0054(11) 0.0016(11) C21 0.0382(13) 0.0365(13) 0.0430(13) 0.0012(10) 0.0089(11) 0.0019(10) C22 0.0475(15) 0.0482(16) 0.0498(15) -0.0037(12) -0.0034(12) -0.0030(12) S01 0.0459(4) 0.0444(4) 0.0678(5) -0.0011(3) -0.0013(3) -0.0070(3) O01 0.0601(12) 0.0454(11) 0.1058(17) -0.0133(11) 0.0211(12) -0.0125(10) C02 0.0668(19) 0.0518(17) 0.072(2) 0.0050(15) 0.0004(16) -0.0130(15) C01 0.071(2) 0.069(2) 0.064(2) 0.0092(16) 0.0042(16) 0.0126(17) S02 0.0257(6) 0.0410(8) 0.0666(9) -0.0142(7) 0.0153(6) -0.0121(6) O02 0.087(5) 0.053(3) 0.078(4) -0.040(3) 0.036(4) -0.019(4) C03 0.102(8) 0.090(13) 0.059(8) -0.008(8) -0.015(6) 0.048(9) C04 0.153(17) 0.071(9) 0.033(5) 0.001(5) 0.027(7) 0.026(9) S02' 0.197(4) 0.092(2) 0.0822(17) -0.0087(14) 0.006(2) 0.033(2) O02' 0.095(5) 0.084(5) 0.079(4) -0.023(3) 0.014(5) 0.015(5) C03' 0.20(2) 0.093(14) 0.078(13) -0.020(10) 0.031(13) -0.036(13) C04' 0.115(15) 0.108(15) 0.107(13) -0.037(10) -0.039(9) 0.017(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 C1 1.302(3) . ? O1 H1A 0.8200 . ? O2 C1 1.199(3) . ? O3 C8 1.203(3) . ? O4 C8 1.316(3) . ? O4 H4A 0.8200 . ? O5 C15 1.370(3) . ? O5 C4 1.397(3) . ? O6 C18 1.358(3) . ? O6 C11 1.406(3) . ? O7 C21 1.369(3) . ? O7 C13 1.389(3) . ? O8 C20 1.362(3) . ? O8 C6 1.396(3) . ? N1 C17 1.319(3) . ? N1 C16 1.334(4) . ? N2 C18 1.319(3) . ? N2 C15 1.325(3) . ? N3 C20 1.315(3) . ? N3 C21 1.321(3) . ? N4 C19 1.321(4) . ? N4 C22 1.333(4) . ? C1 C2 1.496(4) . ? C2 C7 1.386(3) . ? C2 C3 1.390(3) . ? C3 C4 1.375(4) . ? C3 H3A 0.9300 . ? C4 C5 1.376(4) . ? C5 C6 1.376(4) . ? C5 H5A 0.9300 . ? C6 C7 1.378(3) . ? C7 H7A 0.9300 . ? C8 C9 1.495(4) . ? C9 C14 1.386(3) . ? C9 C10 1.392(3) . ? C10 C11 1.373(4) . ? C10 H10A 0.9300 . ? C11 C12 1.380(3) . ? C12 C13 1.382(3) . ? C12 H12A 0.9300 . ? C13 C14 1.373(3) . ? C14 H14A 0.9300 . ? C15 C16 1.376(4) . ? C16 H16A 0.9300 . ? C17 C18 1.385(3) . ? C17 H17A 0.9300 . ? C19 C20 1.387(4) . ? C19 H19A 0.9300 . ? C21 C22 1.373(4) . ? C22 H22A 0.9300 . ? S01 O01 1.515(2) . ? S01 C01 1.774(3) . ? S01 C02 1.783(3) . ? C02 H02A 0.9600 . ? C02 H02B 0.9600 . ? C02 H02C 0.9600 . ? C01 H01A 0.9600 . ? C01 H01B 0.9600 . ? C01 H01C 0.9600 . ? S02 O02 1.571(7) . ? S02 C03 1.753(15) . ? S02 C04 1.854(12) . ? C03 H03A 0.9600 . ? C03 H03B 0.9600 . ? C03 H03C 0.9600 . ? C04 H04A 0.9600 . ? C04 H04B 0.9600 . ? C04 H04C 0.9600 . ? S02' O02' 1.387(9) . ? S02' C04' 1.646(18) . ? S02' C03' 1.66(2) . ? C03' H03D 0.9600 . ? C03' H03E 0.9600 . ? C03' H03F 0.9600 . ? C04' H04D 0.9600 . ? C04' H04E 0.9600 . ? C04' H04F 0.9600 . ? 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 H1A 109.5 . . ? C8 O4 H4A 109.5 . . ? C15 O5 C4 118.3(2) . . ? C18 O6 C11 120.02(19) . . ? C21 O7 C13 121.68(18) . . ? C20 O8 C6 118.62(19) . . ? C17 N1 C16 116.9(2) . . ? C18 N2 C15 114.6(2) . . ? C20 N3 C21 114.5(2) . . ? C19 N4 C22 117.2(2) . . ? O2 C1 O1 123.9(3) . . ? O2 C1 C2 122.9(2) . . ? O1 C1 C2 113.2(2) . . ? C7 C2 C3 120.2(2) . . ? C7 C2 C1 118.1(2) . . ? C3 C2 C1 121.7(2) . . ? C4 C3 C2 118.9(2) . . ? C4 C3 H3A 120.5 . . ? C2 C3 H3A 120.5 . . ? C3 C4 C5 122.0(2) . . ? C3 C4 O5 116.8(2) . . ? C5 C4 O5 121.0(2) . . ? C6 C5 C4 118.1(2) . . ? C6 C5 H5A 121.0 . . ? C4 C5 H5A 121.0 . . ? C5 C6 C7 121.9(2) . . ? C5 C6 O8 119.9(2) . . ? C7 C6 O8 118.0(2) . . ? C6 C7 C2 119.0(2) . . ? C6 C7 H7A 120.5 . . ? C2 C7 H7A 120.5 . . ? O3 C8 O4 124.1(3) . . ? O3 C8 C9 123.4(3) . . ? O4 C8 C9 112.5(2) . . ? C14 C9 C10 119.9(2) . . ? C14 C9 C8 120.7(2) . . ? C10 C9 C8 119.5(2) . . ? C11 C10 C9 118.7(2) . . ? C11 C10 H10A 120.7 . . ? C9 C10 H10A 120.7 . . ? C10 C11 C12 122.7(2) . . ? C10 C11 O6 117.2(2) . . ? C12 C11 O6 119.7(2) . . ? C11 C12 C13 117.3(2) . . ? C11 C12 H12A 121.4 . . ? C13 C12 H12A 121.4 . . ? C14 C13 C12 121.9(2) . . ? C14 C13 O7 115.3(2) . . ? C12 C13 O7 122.5(2) . . ? C13 C14 C9 119.6(2) . . ? C13 C14 H14A 120.2 . . ? C9 C14 H14A 120.2 . . ? N2 C15 O5 118.3(2) . . ? N2 C15 C16 123.9(3) . . ? O5 C15 C16 117.6(3) . . ? N1 C16 C15 120.3(3) . . ? N1 C16 H16A 119.9 . . ? C15 C16 H16A 119.9 . . ? N1 C17 C18 121.3(2) . . ? N1 C17 H17A 119.4 . . ? C18 C17 H17A 119.4 . . ? N2 C18 O6 120.3(2) . . ? N2 C18 C17 123.0(2) . . ? O6 C18 C17 116.7(2) . . ? N4 C19 C20 120.4(3) . . ? N4 C19 H19A 119.8 . . ? C20 C19 H19A 119.8 . . ? N3 C20 O8 120.0(2) . . ? N3 C20 C19 123.6(2) . . ? O8 C20 C19 116.3(2) . . ? N3 C21 O7 119.7(2) . . ? N3 C21 C22 123.9(2) . . ? O7 C21 C22 116.3(2) . . ? N4 C22 C21 120.4(2) . . ? N4 C22 H22A 119.8 . . ? C21 C22 H22A 119.8 . . ? O01 S01 C01 104.83(15) . . ? O01 S01 C02 103.59(14) . . ? C01 S01 C02 99.61(16) . . ? S01 C02 H02A 109.5 . . ? S01 C02 H02B 109.5 . . ? H02A C02 H02B 109.5 . . ? S01 C02 H02C 109.5 . . ? H02A C02 H02C 109.5 . . ? H02B C02 H02C 109.5 . . ? S01 C01 H01A 109.5 . . ? S01 C01 H01B 109.5 . . ? H01A C01 H01B 109.5 . . ? S01 C01 H01C 109.5 . . ? H01A C01 H01C 109.5 . . ? H01B C01 H01C 109.5 . . ? O02 S02 C03 99.9(9) . . ? O02 S02 C04 102.9(7) . . ? C03 S02 C04 97.5(11) . . ? S02 C03 H03A 109.5 . . ? S02 C03 H03B 109.5 . . ? H03A C03 H03B 109.5 . . ? S02 C03 H03C 109.5 . . ? H03A C03 H03C 109.5 . . ? H03B C03 H03C 109.5 . . ? S02 C04 H04A 109.5 . . ? S02 C04 H04B 109.5 . . ? H04A C04 H04B 109.5 . . ? S02 C04 H04C 109.5 . . ? H04A C04 H04C 109.5 . . ? H04B C04 H04C 109.5 . . ? O02' S02' C04' 108.5(10) . . ? O02' S02' C03' 122.7(11) . . ? C04' S02' C03' 102.7(14) . . ? S02' C03' H03D 109.5 . . ? S02' C03' H03E 109.5 . . ? H03D C03' H03E 109.5 . . ? S02' C03' H03F 109.5 . . ? H03D C03' H03F 109.5 . . ? H03E C03' H03F 109.5 . . ? S02' C04' H04D 109.5 . . ? S02' C04' H04E 109.5 . . ? H04D C04' H04E 109.5 . . ? S02' C04' H04F 109.5 . . ? H04D C04' H04F 109.5 . . ? H04E C04' H04F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C7 -3.3(4) . . . . ? O1 C1 C2 C7 175.0(2) . . . . ? O2 C1 C2 C3 179.2(3) . . . . ? O1 C1 C2 C3 -2.5(4) . . . . ? C7 C2 C3 C4 -1.0(4) . . . . ? C1 C2 C3 C4 176.4(2) . . . . ? C2 C3 C4 C5 0.8(4) . . . . ? C2 C3 C4 O5 175.3(2) . . . . ? C15 O5 C4 C3 142.7(3) . . . . ? C15 O5 C4 C5 -42.7(4) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? O5 C4 C5 C6 -174.5(2) . . . . ? C4 C5 C6 C7 -0.3(4) . . . . ? C4 C5 C6 O8 174.5(2) . . . . ? C20 O8 C6 C5 72.3(3) . . . . ? C20 O8 C6 C7 -112.7(3) . . . . ? C5 C6 C7 C2 0.0(4) . . . . ? O8 C6 C7 C2 -174.9(2) . . . . ? C3 C2 C7 C6 0.6(4) . . . . ? C1 C2 C7 C6 -176.9(2) . . . . ? O3 C8 C9 C14 174.9(3) . . . . ? O4 C8 C9 C14 -4.9(4) . . . . ? O3 C8 C9 C10 -4.2(4) . . . . ? O4 C8 C9 C10 176.0(2) . . . . ? C14 C9 C10 C11 0.7(4) . . . . ? C8 C9 C10 C11 179.8(2) . . . . ? C9 C10 C11 C12 0.8(4) . . . . ? C9 C10 C11 O6 -172.3(2) . . . . ? C18 O6 C11 C10 -129.5(3) . . . . ? C18 O6 C11 C12 57.2(3) . . . . ? C10 C11 C12 C13 -2.2(4) . . . . ? O6 C11 C12 C13 170.8(2) . . . . ? C11 C12 C13 C14 2.2(4) . . . . ? C11 C12 C13 O7 -171.3(2) . . . . ? C21 O7 C13 C14 151.2(2) . . . . ? C21 O7 C13 C12 -35.0(3) . . . . ? C12 C13 C14 C9 -0.7(4) . . . . ? O7 C13 C14 C9 173.1(2) . . . . ? C10 C9 C14 C13 -0.7(4) . . . . ? C8 C9 C14 C13 -179.8(2) . . . . ? C18 N2 C15 O5 -176.2(2) . . . . ? C18 N2 C15 C16 -0.5(4) . . . . ? C4 O5 C15 N2 -45.7(4) . . . . ? C4 O5 C15 C16 138.3(3) . . . . ? C17 N1 C16 C15 -0.6(4) . . . . ? N2 C15 C16 N1 1.1(4) . . . . ? O5 C15 C16 N1 176.7(3) . . . . ? C16 N1 C17 C18 -0.3(4) . . . . ? C15 N2 C18 O6 177.0(2) . . . . ? C15 N2 C18 C17 -0.4(4) . . . . ? C11 O6 C18 N2 24.8(4) . . . . ? C11 O6 C18 C17 -157.7(2) . . . . ? N1 C17 C18 N2 0.9(4) . . . . ? N1 C17 C18 O6 -176.6(2) . . . . ? C22 N4 C19 C20 -0.4(4) . . . . ? C21 N3 C20 O8 178.0(2) . . . . ? C21 N3 C20 C19 0.6(3) . . . . ? C6 O8 C20 N3 12.8(3) . . . . ? C6 O8 C20 C19 -169.7(2) . . . . ? N4 C19 C20 N3 -0.3(4) . . . . ? N4 C19 C20 O8 -177.7(2) . . . . ? C20 N3 C21 O7 -175.7(2) . . . . ? C20 N3 C21 C22 -0.3(3) . . . . ? C13 O7 C21 N3 -39.9(3) . . . . ? C13 O7 C21 C22 144.4(2) . . . . ? C19 N4 C22 C21 0.7(4) . . . . ? N3 C21 C22 N4 -0.4(4) . . . . ? O7 C21 C22 N4 175.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.601 _refine_diff_density_min -0.857 _refine_diff_density_rms 0.044