Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_global #=============================================================================== _audit_creation_date 12-10-99 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Klotz, Philippe' 'Mann, Andre' 'Schoenfelder, Angele' 'Ungureanu, Ioana' _publ_contact_author_name 'Dr Andre Mann' _publ_contact_author_address ; Dr Andre Mann UMR 7081 Faculte de Pharmacie Laboratoire de Pharmacochimie de la Communication Cellulaire 74 route du Rhin, BP 24 Illkirch F-67401 FRANCE ; #=============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; ? ; _publ_section_exptl_refinement ; ? ; _publ_section_references ; Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Polidori, G., Spagna, R. &Viterbo, D. (1989). SIR. J. Appl. Cryst. 22, 389-393. OpenMoleN, Interactive Intelligent Structure solution (1997) Nonius B.V., Delft, The Netherlands. KappaCCD Operation Manual (1997), Nonius B.V., Delft, The Nederlands. Otwinowski, Z. & Minor, W. (1997), Methods in Enzymology, 276, 307-326. ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; data_st487 _database_code_CSD 142897 #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C21 H25 N O3 S' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C21 H25 N O3 S' _chemical_formula_weight 371.50 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1 H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 N ? 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1 O ? 0.008 0.006 International_Tables_Vol_IV_Table_2.3.1 S ? 0.110 0.124 International_Tables_Vol_IV_Table_2.3.1 #=============================================================================== # 6. CRYSTAL DATA _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 7.6170(4) _cell_length_b 11.0840(6) _cell_length_c 12.3600(6) _cell_angle_alpha 86.392(4) _cell_angle_beta 73.692(4) _cell_angle_gamma 78.942(4) _cell_volume 982.9(1) _cell_formula_units_Z 2 _cell_measurement_temperature 294 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_special_details ; Cell parameters refined using Scalepack part of DENZO Z. Otwinowski, W. Minor, 1997 ; _exptl_crystal_description plate _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.26 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.184 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=============================================================================== # 7. EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 294 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_source xray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\p scans' _diffrn_measurement_details ; 10796 reflections were collected using program Collect ("Collect" Data collection software, Nonius B.V., 1998) The conditions were as follow : crystal to detector distance = 35. mm. Scan angle = 2.0 deg 1 scans of 180 sec per frame. Data collection was divided into 4 sets with the following starting angles and number of frames : Set 1 Theta = 8.10 Omega = 180.00 Kappa = 0.00 91 frames Set 2 Theta = -7.90 Kappa = 137.00 Phi = 0.00 29 frames Set 3 Theta = 6.10 Kappa = -38.00 Phi = 0.00 49 frames Set 4 Theta = -7.90 Kappa = 105.00 Phi = 0.00 25 frames Friedel pairs were averaged. Internal R = 0.03 ; _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10796 _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 27.58 _reflns_number_total 4351 _reflns_number_gt 3037 _reflns_threshold_expression >3.0\s(I) _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_OpenMoleN_(_1997) _computing_molecular_graphics ? _computing_publication_material CIFGEN_IN_OpenMoleN_(_1997) #=============================================================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme '4Fo^2^/(\s^2^(Fo^2^)+0.0004 Fo^4^)+1.0' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_expression ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3037 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.077 _refine_ls_R_factor_gt 0.044 _refine_ls_wR_factor_all 0.068 _refine_ls_wR_factor_ref 0.057 _refine_ls_goodness_of_fit_all 1.549 _refine_ls_goodness_of_fit_ref 1.295 _refine_ls_shift/su_max 0.003 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.211 _refine_diff_density_min -0.407 #=============================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol S 0.66195(7) 0.16123(5) 0.02568(4) 0.0454(2) Uani ? ? S O1 0.5024(2) 0.2208(2) -0.0098(1) 0.0609(8) Uani ? ? O O2 0.8130(2) 0.0854(2) -0.0521(1) 0.0569(8) Uani ? ? O N 0.5880(2) 0.0733(1) 0.1339(1) 0.0405(7) Uani ? ? N C1 0.7276(2) 0.0011(2) 0.1867(2) 0.046(1) Uani ? ? C C2 0.6567(3) -0.1117(2) 0.2434(2) 0.048(1) Uani ? ? C C3 0.4665(2) -0.0780(2) 0.3307(1) 0.0413(8) Uani ? ? C C4 0.3971(2) -0.1905(2) 0.3898(2) 0.0425(9) Uani ? ? C C5 0.3481(3) -0.2779(2) 0.3329(2) 0.060(1) Uani ? ? C C6 0.2911(4) -0.3824(2) 0.3874(2) 0.072(1) Uani ? ? C C7 0.2806(3) -0.4022(2) 0.5002(2) 0.065(1) Uani ? ? C C8 0.3263(3) -0.3172(2) 0.5582(2) 0.064(1) Uani ? ? C C9 0.3835(3) -0.2123(2) 0.5036(2) 0.052(1) Uani ? ? C C10 0.3273(2) 0.0023(2) 0.2738(1) 0.0408(8) Uani ? ? C C11 0.1388(3) 0.0518(2) 0.3569(2) 0.049(1) Uani ? ? C C12 0.1533(3) 0.1502(2) 0.4329(2) 0.048(1) Uani ? ? C C13 0.2430(3) 0.2500(2) 0.3621(2) 0.051(1) Uani ? ? C O3 0.4200(2) 0.2002(1) 0.2861(1) 0.0445(6) Uani ? ? O C14 0.4044(2) 0.1120(2) 0.2106(1) 0.0389(8) Uani ? ? C C15 0.7565(3) 0.2760(2) 0.0714(2) 0.045(1) Uani ? ? C C16 0.6469(3) 0.3892(2) 0.1059(2) 0.059(1) Uani ? ? C C17 0.7225(3) 0.4781(2) 0.1413(2) 0.065(1) Uani ? ? C C18 0.9072(3) 0.4574(2) 0.1435(2) 0.057(1) Uani ? ? C C19 0.9886(4) 0.5535(3) 0.1841(2) 0.085(2) Uani ? ? C C20 1.0159(3) 0.3442(2) 0.1067(2) 0.060(1) Uani ? ? C C21 0.9429(3) 0.2534(2) 0.0715(2) 0.052(1) Uani ? ? C H1 0.7474 0.0499 0.2411 0.0633 Uiso calc C1 H H2 0.8414 -0.0232 0.1305 0.0633 Uiso calc C1 H H3 0.7437 -0.1555 0.2804 0.0649 Uiso calc C2 H H4 0.6448 -0.1624 0.1876 0.0649 Uiso calc C2 H H5 0.4796 -0.0308 0.3886 0.0539 Uiso calc C3 H H6 0.3539 -0.2654 0.2553 0.0802 Uiso calc C5 H H7 0.2589 -0.4410 0.3468 0.0949 Uiso calc C6 H H8 0.2421 -0.4742 0.5373 0.0903 Uiso calc C7 H H9 0.3188 -0.3300 0.6360 0.0848 Uiso calc C8 H H10 0.4143 -0.1540 0.5451 0.0671 Uiso calc C9 H H11 0.0950 -0.0143 0.4026 0.0660 Uiso calc C11 H H12 0.0530 0.0861 0.3155 0.0660 Uiso calc C11 H H13 0.2267 0.1142 0.4813 0.0680 Uiso calc C12 H H14 0.0323 0.1851 0.4769 0.0680 Uiso calc C12 H H15 0.2611 0.3068 0.4107 0.0707 Uiso calc C13 H H16 0.1629 0.2912 0.3195 0.0707 Uiso calc C13 H H17 0.3089 -0.0515 0.2227 0.0531 Uiso calc C10 H H18 0.3187 0.1487 0.1699 0.0527 Uiso calc C14 H H19 0.5201 0.4057 0.1051 0.0845 Uiso calc C16 H H20 0.6462 0.5554 0.1649 0.0952 Uiso calc C17 H H21 1.1158 0.5227 0.1793 0.1129 Uiso calc C19 H H22 0.9789 0.6254 0.1384 0.1129 Uiso calc C19 H H23 0.9225 0.5731 0.2602 0.1129 Uiso calc C19 H H24 1.1434 0.3286 0.1058 0.0775 Uiso calc C20 H H25 1.0193 0.1763 0.0476 0.0696 Uiso calc C21 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol S 0.0427(2) 0.0726(3) 0.0301(2) -0.0076(2) -0.0048(2) 0.0036(2) S O1 0.0513(7) 0.100(1) 0.0439(7) -0.0109(7) -0.0174(6) 0.0191(8) O O2 0.0534(7) 0.093(1) 0.0370(7) -0.0104(7) 0.0019(6) -0.0142(7) O N 0.0342(7) 0.0541(9) 0.0359(7) -0.0033(6) -0.0052(6) 0.0017(7) N C1 0.0349(8) 0.058(1) 0.048(1) 0.0005(8) -0.0079(8) -0.0003(9) C C2 0.0452(9) 0.049(1) 0.050(1) 0.0026(8) -0.0114(8) -0.0018(9) C C3 0.0443(8) 0.0428(9) 0.0372(8) -0.0046(7) -0.0127(7) -0.0033(7) C C4 0.0450(9) 0.0415(9) 0.0412(8) -0.0026(7) -0.0110(7) -0.0027(8) C C5 0.085(1) 0.054(1) 0.049(1) -0.018(1) -0.0169(9) -0.0048(9) C C6 0.095(1) 0.052(1) 0.075(1) -0.024(1) -0.019(1) -0.005(1) C C7 0.071(1) 0.048(1) 0.082(2) -0.014(1) -0.010(1) 0.014(1) C C8 0.070(1) 0.067(1) 0.056(1) -0.008(1) -0.018(1) 0.015(1) C C9 0.057(1) 0.054(1) 0.0454(9) -0.0086(9) -0.0182(8) 0.0035(9) C C10 0.0390(8) 0.048(1) 0.0362(8) -0.0078(7) -0.0110(6) -0.0027(7) C C11 0.0382(9) 0.058(1) 0.051(1) -0.0093(8) -0.0068(8) 0.009(1) C C12 0.045(1) 0.056(1) 0.044(1) 0.0023(9) 0.0009(9) -0.0004(9) C C13 0.052(1) 0.050(1) 0.049(1) 0.0029(9) -0.0028(9) -0.004(1) C O3 0.0447(6) 0.0459(7) 0.0428(6) -0.0082(5) -0.0031(5) -0.0040(6) O C14 0.0340(8) 0.050(1) 0.0344(8) -0.0021(7) -0.0088(7) 0.0011(8) C C15 0.0437(9) 0.054(1) 0.0376(9) -0.0044(9) -0.0026(8) 0.0097(9) C C16 0.047(1) 0.059(1) 0.075(1) -0.004(1) -0.001(1) 0.012(1) C C17 0.070(1) 0.050(1) 0.078(2) -0.000(1) 0.006(1) 0.005(1) C C18 0.076(1) 0.051(1) 0.048(1) -0.015(1) -0.009(1) 0.012(1) C C19 0.119(2) 0.069(1) 0.076(2) -0.031(1) -0.024(1) 0.008(1) C C20 0.059(1) 0.062(1) 0.060(1) -0.010(1) -0.0227(9) 0.014(1) C C21 0.052(1) 0.054(1) 0.051(1) -0.0008(9) -0.0150(8) 0.0044(9) C # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S O1 1.435(2) . . ? S O2 1.436(1) . . ? S N 1.637(2) . . ? S C15 1.768(2) . . ? N C1 1.482(3) . . ? N C14 1.454(2) . . ? C1 C2 1.511(3) . . ? C2 C3 1.539(3) . . ? C3 C4 1.514(3) . . ? C3 C10 1.545(3) . . ? C4 C5 1.394(3) . . ? C4 C9 1.391(3) . . ? C5 C6 1.384(3) . . ? C6 C7 1.380(4) . . ? C7 C8 1.369(4) . . ? C8 C9 1.388(3) . . ? C10 C11 1.536(3) . . ? C10 C14 1.527(3) . . ? C11 C12 1.522(3) . . ? C12 C13 1.512(3) . . ? C13 O3 1.440(2) . . ? O3 C14 1.436(2) . . ? C15 C16 1.385(3) . . ? C15 C21 1.394(3) . . ? C16 C17 1.382(4) . . ? C17 C18 1.389(4) . . ? C18 C19 1.506(4) . . ? C18 C20 1.389(3) . . ? C20 C21 1.384(3) . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S O2 119.63(9) . . . ? O1 S N 107.16(9) . . . ? O1 S C15 107.9(1) . . . ? O2 S N 106.47(9) . . . ? O2 S C15 106.90(9) . . . ? N S C15 108.31(9) . . . ? S N C1 117.8(1) . . . ? S N C14 119.0(1) . . . ? C1 N C14 115.1(1) . . . ? N C1 C2 109.2(2) . . . ? C1 C2 C3 111.8(2) . . . ? C2 C3 C4 112.0(2) . . . ? C2 C3 C10 109.6(2) . . . ? C4 C3 C10 113.0(2) . . . ? C3 C4 C5 122.0(2) . . . ? C3 C4 C9 120.9(2) . . . ? C5 C4 C9 117.1(2) . . . ? C4 C5 C6 121.2(2) . . . ? C5 C6 C7 120.4(2) . . . ? C6 C7 C8 119.5(2) . . . ? C7 C8 C9 120.1(2) . . . ? C4 C9 C8 121.7(2) . . . ? C3 C10 C11 113.4(2) . . . ? C3 C10 C14 111.9(1) . . . ? C11 C10 C14 107.8(2) . . . ? C10 C11 C12 111.9(2) . . . ? C11 C12 C13 110.0(2) . . . ? C12 C13 O3 111.6(2) . . . ? C13 O3 C14 112.3(1) . . . ? N C14 C10 111.2(2) . . . ? N C14 O3 107.7(1) . . . ? C10 C14 O3 112.0(1) . . . ? S C15 C16 120.4(2) . . . ? S C15 C21 120.0(2) . . . ? C16 C15 C21 119.6(2) . . . ? C15 C16 C17 119.7(2) . . . ? C16 C17 C18 121.8(2) . . . ? C17 C18 C19 121.7(2) . . . ? C17 C18 C20 117.7(2) . . . ? C19 C18 C20 120.6(2) . . . ? C18 C20 C21 121.6(2) . . . ? C15 C21 C20 119.6(2) . . . ? data_st526 _database_code_CSD 142898 #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C22 H27 N O2 S' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C22 H27 N O2 S' _chemical_formula_weight 369.53 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1 H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 N ? 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1 O ? 0.008 0.006 International_Tables_Vol_IV_Table_2.3.1 S ? 0.110 0.124 International_Tables_Vol_IV_Table_2.3.1 #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 9.4881(3) _cell_length_b 18.6503(8) _cell_length_c 11.1767(5) _cell_angle_alpha 90 _cell_angle_beta 101.626(8) _cell_angle_gamma 90 _cell_volume 1937.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_special_details ; Cell parameters refined using Scalepack part of DENZO Z. Otwinowski, W. Minor, 1997 ; _exptl_crystal_description prism _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.27 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.183 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=============================================================================== # 7. EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_source xray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\p scans' _diffrn_measurement_details ; 8028 reflections were collected using program Collect ("Collect" Data collection software, Nonius B.V., 1998) The conditions were as follow : crystal to detector distance = 35. mm. Scan angle = 2.0 deg 1 scans of 30 sec per frame. Data collection was divided into 3 set(s) with the following starting angles and number of frames : Set 1 Theta = 6.00 Omega = 0.00 Kappa = 0.00 90 frames Set 2 Theta = -4.50 Kappa = -172.00 Phi = 0.00 21 frames Set 3 Theta = -5.20 Kappa = -167.00 Phi = 0.00 20 frames Friedel pairs were averaged. Internal R = 0.04 ; _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8028 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4539 _reflns_number_gt 2079 _reflns_threshold_expression >3.0\s(I) _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_OpenMoleN_(_1997) _computing_molecular_graphics ? _computing_publication_material CIFGEN_IN_OpenMoleN_(_1997) #=============================================================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme '4Fo^2^/(\s^2^(Fo^2^) + 0.0064 Fo^4^)' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_expression ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2079 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.104 _refine_ls_R_factor_gt 0.046 _refine_ls_wR_factor_all 0.122 _refine_ls_wR_factor_ref 0.067 _refine_ls_goodness_of_fit_all 2.291 _refine_ls_goodness_of_fit_ref 1.213 _refine_ls_shift/su_max 0.018 _refine_ls_shift/esd_mean 0.004 _refine_diff_density_max 0.284 _refine_diff_density_min -0.279 #=============================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol S 0.45587(7) 0.25493(4) 1.06096(7) 0.0513(4) Uani ? ? S O1 0.4917(2) 0.3204(1) 1.1285(2) 0.072(1) Uani ? ? O O2 0.3507(2) 0.2566(1) 0.9481(2) 0.065(1) Uani ? ? O C1 0.3930(2) 0.1932(2) 1.1594(2) 0.044(1) Uani ? ? C C2 0.2597(3) 0.1600(2) 1.1228(2) 0.049(2) Uani ? ? C C3 0.2118(3) 0.1131(2) 1.2010(3) 0.054(2) Uani ? ? C C4 0.2942(3) 0.0966(2) 1.3160(2) 0.050(2) Uani ? ? C C5 0.4283(3) 0.1303(2) 1.3493(2) 0.053(2) Uani ? ? C C6 0.4757(3) 0.1782(2) 1.2734(2) 0.049(2) Uani ? ? C C7 0.2382(3) 0.0455(2) 1.3993(3) 0.077(2) Uani ? ? C N 0.6067(2) 0.2220(1) 1.0409(2) 0.043(1) Uani ? ? N C8 0.7429(3) 0.2626(2) 1.0820(3) 0.053(2) Uani ? ? C C9 0.8593(3) 0.2156(2) 1.0453(3) 0.052(2) Uani ? ? C C10 0.7869(2) 0.1433(1) 1.0014(2) 0.040(1) Uani ? ? C C11 0.6264(2) 0.1659(1) 0.9487(2) 0.038(1) Uani ? ? C C12 0.6134(3) 0.2010(2) 0.8211(2) 0.048(2) Uani ? ? C C13 0.6220(3) 0.1475(2) 0.7207(2) 0.055(2) Uani ? ? C C14 0.5149(3) 0.0877(2) 0.7157(3) 0.053(2) Uani ? ? C C15 0.5294(3) 0.0515(1) 0.8395(2) 0.045(2) Uani ? ? C C16 0.5161(2) 0.1052(1) 0.9403(2) 0.039(1) Uani ? ? C C17 0.8102(2) 0.0868(1) 1.1016(2) 0.039(1) Uani ? ? C C18 0.8447(2) 0.0162(2) 1.0763(3) 0.047(2) Uani ? ? C C19 0.8738(3) -0.0348(2) 1.1677(3) 0.054(2) Uani ? ? C C20 0.8655(3) -0.0172(2) 1.2874(3) 0.057(2) Uani ? ? C C21 0.8326(3) 0.0511(2) 1.3143(3) 0.057(2) Uani ? ? C C22 0.8043(3) 0.1025(2) 1.2233(2) 0.050(2) Uani ? ? C H1 0.2023 0.1697 1.0446 0.0646 Uiso calc C2 H H2 0.1201 0.0913 1.1760 0.0711 Uiso calc C3 H H3 0.4877 0.1196 1.4263 0.0705 Uiso calc C5 H H4 0.5659 0.2013 1.2991 0.0643 Uiso calc C6 H H5 0.1460 0.0286 1.3601 0.0969 Uiso calc C7 H H6 0.3024 0.0061 1.4177 0.0969 Uiso calc C7 H H7 0.2307 0.0695 1.4727 0.0969 Uiso calc C7 H H8 0.7614 0.2695 1.1680 0.0726 Uiso calc C8 H H9 0.7383 0.3079 1.0424 0.0726 Uiso calc C8 H H10 0.9358 0.2082 1.1134 0.0675 Uiso calc C9 H H11 0.8956 0.2377 0.9811 0.0675 Uiso calc C9 H H12 0.8266 0.1194 0.9408 0.0521 Uiso calc C10 H H13 0.6893 0.2347 0.8251 0.0628 Uiso calc C12 H H14 0.5236 0.2251 0.8011 0.0628 Uiso calc C12 H H15 0.7161 0.1276 0.7350 0.0730 Uiso calc C13 H H16 0.6038 0.1718 0.6445 0.0730 Uiso calc C13 H H17 0.5310 0.0532 0.6574 0.0710 Uiso calc C14 H H18 0.4205 0.1066 0.6920 0.0710 Uiso calc C14 H H19 0.6208 0.0289 0.8596 0.0607 Uiso calc C15 H H20 0.4558 0.0164 0.8347 0.0607 Uiso calc C15 H H21 0.4221 0.1252 0.9234 0.0516 Uiso calc C16 H H22 0.5312 0.0806 1.0163 0.0516 Uiso calc C16 H H23 0.8481 0.0030 0.9948 0.0627 Uiso calc C18 H H24 0.8996 -0.0821 1.1490 0.0769 Uiso calc C19 H H25 0.8827 -0.0526 1.3497 0.0763 Uiso calc C20 H H26 0.8291 0.0636 1.3960 0.0741 Uiso calc C21 H H27 0.7801 0.1498 1.2438 0.0648 Uiso calc C22 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol S 0.0548(4) 0.0384(4) 0.0640(5) 0.0067(3) 0.0115(4) -0.0004(4) S O1 0.089(1) 0.037(1) 0.112(2) -0.000(1) 0.027(1) -0.021(1) O O2 0.058(1) 0.066(1) 0.070(1) 0.016(1) -0.001(1) 0.017(1) O C1 0.042(1) 0.044(1) 0.046(1) 0.004(1) 0.011(1) -0.011(1) C C2 0.042(1) 0.057(2) 0.050(2) 0.003(1) 0.009(1) -0.010(2) C C3 0.045(1) 0.059(2) 0.060(2) -0.006(1) 0.010(1) -0.021(2) C C4 0.053(1) 0.053(2) 0.046(2) 0.001(1) 0.014(1) -0.013(1) C C5 0.045(1) 0.071(2) 0.046(2) 0.004(1) 0.009(1) -0.008(2) C C6 0.039(1) 0.061(2) 0.049(2) -0.004(1) 0.011(1) -0.007(1) C C7 0.080(2) 0.082(2) 0.070(2) -0.008(2) 0.035(1) -0.003(2) C N 0.047(1) 0.036(1) 0.047(1) -0.0071(9) 0.009(1) -0.005(1) N C8 0.060(2) 0.039(2) 0.062(2) -0.013(1) -0.002(1) 0.001(2) C C9 0.046(1) 0.055(2) 0.055(2) -0.012(1) 0.010(1) 0.007(2) C C10 0.038(1) 0.043(1) 0.040(1) -0.005(1) 0.010(1) 0.000(1) C C11 0.044(1) 0.032(1) 0.040(1) -0.004(1) 0.007(1) 0.003(1) C C12 0.057(2) 0.043(2) 0.044(2) -0.007(1) 0.009(1) 0.009(1) C C13 0.062(2) 0.064(2) 0.041(2) -0.001(2) 0.008(1) 0.010(2) C C14 0.061(2) 0.055(2) 0.045(2) 0.001(1) 0.003(1) -0.004(2) C C15 0.044(1) 0.039(1) 0.051(2) -0.004(1) -0.004(1) -0.000(1) C C16 0.038(1) 0.038(1) 0.042(1) -0.006(1) 0.004(1) 0.002(1) C C17 0.033(1) 0.041(1) 0.043(1) -0.002(1) 0.005(1) -0.003(1) C C18 0.041(1) 0.048(2) 0.053(2) 0.004(1) 0.002(1) -0.006(1) C C19 0.055(2) 0.038(2) 0.077(2) 0.006(1) -0.004(2) 0.003(2) C C20 0.054(2) 0.055(2) 0.063(2) 0.001(1) 0.003(1) 0.019(2) C C21 0.062(2) 0.063(2) 0.047(2) 0.007(1) 0.014(1) 0.010(2) C C22 0.054(1) 0.045(2) 0.051(2) 0.007(1) 0.013(1) 0.005(1) C # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S O1 1.439(2) . . ? S O2 1.442(2) . . ? S C1 1.777(3) . . ? S N 1.613(2) . . ? C1 C2 1.393(4) . . ? C1 C6 1.383(4) . . ? C2 C3 1.376(4) . . ? C3 C4 1.398(4) . . ? C4 C5 1.400(4) . . ? C4 C7 1.502(5) . . ? C5 C6 1.370(4) . . ? N C8 1.489(4) . . ? N C11 1.507(4) . . ? C8 C9 1.530(5) . . ? C9 C10 1.548(4) . . ? C10 C11 1.576(4) . . ? C10 C17 1.520(4) . . ? C11 C12 1.551(4) . . ? C11 C16 1.532(4) . . ? C12 C13 1.516(4) . . ? C13 C14 1.503(4) . . ? C14 C15 1.521(4) . . ? C15 C16 1.531(4) . . ? C17 C18 1.400(4) . . ? C17 C22 1.404(4) . . ? C18 C19 1.382(4) . . ? C19 C20 1.395(5) . . ? C20 C21 1.358(5) . . ? C21 C22 1.385(4) . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S O2 119.3(1) . . . ? O1 S C1 107.4(1) . . . ? O1 S N 105.8(1) . . . ? O2 S C1 107.2(1) . . . ? O2 S N 111.3(1) . . . ? C1 S N 104.9(1) . . . ? S C1 C2 120.3(3) . . . ? S C1 C6 120.1(2) . . . ? C2 C1 C6 119.6(3) . . . ? C1 C2 C3 119.5(3) . . . ? C2 C3 C4 121.9(3) . . . ? C3 C4 C5 117.1(3) . . . ? C3 C4 C7 120.5(3) . . . ? C5 C4 C7 122.4(3) . . . ? C4 C5 C6 121.4(3) . . . ? C1 C6 C5 120.4(3) . . . ? S N C8 120.2(2) . . . ? S N C11 126.5(2) . . . ? C8 N C11 110.1(2) . . . ? N C8 C9 104.8(2) . . . ? C8 C9 C10 106.6(2) . . . ? C9 C10 C11 102.6(2) . . . ? C9 C10 C17 112.4(2) . . . ? C11 C10 C17 116.5(2) . . . ? N C11 C10 100.1(2) . . . ? N C11 C12 109.7(2) . . . ? N C11 C16 112.2(2) . . . ? C10 C11 C12 110.4(2) . . . ? C10 C11 C16 114.9(2) . . . ? C12 C11 C16 109.2(2) . . . ? C11 C12 C13 113.4(2) . . . ? C12 C13 C14 112.3(2) . . . ? C13 C14 C15 111.0(3) . . . ? C14 C15 C16 111.9(2) . . . ? C11 C16 C15 111.9(2) . . . ? C10 C17 C18 120.5(3) . . . ? C10 C17 C22 122.7(3) . . . ? C18 C17 C22 116.7(3) . . . ? C17 C18 C19 121.2(3) . . . ? C18 C19 C20 120.4(3) . . . ? C19 C20 C21 119.5(3) . . . ? C20 C21 C22 120.5(3) . . . ? C17 C22 C21 121.8(3) . . . ?