# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Yoshitane Imai' _publ_contact_author_email Y-IMAI@APCH.KINDAI.AC.JP _publ_section_title ; Development of novel thioether molecular skeleton for spontaneous chiral crystallization ; loop_ _publ_author_name 'Yoshitane Imai' 'Takafumi Kinuta' 'Reiko Kuroda' 'Yoshio Matsubara' 'Tomohiro Sato' 'Nobuo Tajima' ; E.Yokoyama ; # Attachment 'IMAI913ver2.CIF' data_imai913_2a _database_code_depnum_ccdc_archive 'CCDC 749801' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H16 O S' _chemical_formula_weight 268.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.5932(8) _cell_length_b 11.4042(8) _cell_length_c 11.6692(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1409.72(18) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2838 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 27.87 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.218 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9177 _exptl_absorpt_correction_T_max 0.9474 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12420 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 27.87 _reflns_number_total 3285 _reflns_number_gt 2838 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0939P)^2^+0.0987P] 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 -0.03(10) _refine_ls_number_reflns 3285 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0636 _refine_ls_R_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.1480 _refine_ls_wR_factor_gt 0.1417 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5354(2) 0.01663(19) 0.17761(18) 0.0539(5) Uani 1 1 d . . . C2 C 0.4658(3) 0.1094(2) 0.1158(2) 0.0657(7) Uani 1 1 d . . . C3 C 0.5337(4) 0.1682(3) 0.0190(3) 0.0928(11) Uani 1 1 d . . . H3A H 0.5068 0.2493 0.0146 0.111 Uiso 1 1 calc R . . H3B H 0.5103 0.1303 -0.0523 0.111 Uiso 1 1 calc R . . C4 C 0.6765(4) 0.1643(3) 0.0316(3) 0.1003(12) Uani 1 1 d . . . H4A H 0.7156 0.1948 -0.0374 0.120 Uiso 1 1 calc R . . H4B H 0.7019 0.2137 0.0953 0.120 Uiso 1 1 calc R . . C5 C 0.7206(4) 0.0428(3) 0.0519(3) 0.0999(12) Uani 1 1 d . . . H5A H 0.8102 0.0442 0.0690 0.120 Uiso 1 1 calc R . . H5B H 0.7089 -0.0026 -0.0176 0.120 Uiso 1 1 calc R . . C6 C 0.6521(3) -0.0169(2) 0.1488(2) 0.0663(6) Uani 1 1 d . . . C7 C 0.7214(4) -0.1141(4) 0.2034(4) 0.1068(12) Uani 1 1 d . . . H7A H 0.6831 -0.1323 0.2758 0.160 Uiso 1 1 calc R . . H7B H 0.8076 -0.0913 0.2152 0.160 Uiso 1 1 calc R . . H7C H 0.7184 -0.1818 0.1547 0.160 Uiso 1 1 calc R . . O2 O 0.3586(2) 0.13475(19) 0.1395(2) 0.0902(7) Uani 1 1 d . . . S8 S 0.44962(7) -0.05980(5) 0.28381(5) 0.0658(2) Uani 1 1 d . . . C9 C 0.5137(2) 0.1369(2) 0.4111(2) 0.0548(5) Uani 1 1 d . . . H9 H 0.5641 0.1614 0.3504 0.066 Uiso 1 1 calc R . . C10 C 0.4468(2) 0.03630(19) 0.40195(18) 0.0516(5) Uani 1 1 d . . . C11 C 0.3689(2) -0.0010(2) 0.4943(2) 0.0585(5) Uani 1 1 d . . . H11 H 0.3227 -0.0700 0.4878 0.070 Uiso 1 1 calc R . . C12 C 0.3617(2) 0.0634(2) 0.5920(2) 0.0612(6) Uani 1 1 d . . . H12 H 0.3108 0.0378 0.6519 0.073 Uiso 1 1 calc R . . C13 C 0.4256(3) 0.2355(3) 0.7062(2) 0.0761(7) Uani 1 1 d . . . H13 H 0.3738 0.2125 0.7664 0.091 Uiso 1 1 calc R . . C14 C 0.4970(4) 0.3337(3) 0.7159(3) 0.0868(9) Uani 1 1 d . . . H14 H 0.4944 0.3772 0.7833 0.104 Uiso 1 1 calc R . . C15 C 0.5744(3) 0.3701(3) 0.6261(3) 0.0820(8) Uani 1 1 d . . . H15 H 0.6238 0.4369 0.6346 0.098 Uiso 1 1 calc R . . C16 C 0.5783(3) 0.3089(2) 0.5263(2) 0.0706(7) Uani 1 1 d . . . H16 H 0.6284 0.3355 0.4662 0.085 Uiso 1 1 calc R . . C17 C 0.5075(2) 0.2060(2) 0.51322(19) 0.0555(5) Uani 1 1 d . . . C18 C 0.4299(2) 0.1674(2) 0.6035(2) 0.0560(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0648(13) 0.0527(10) 0.0441(10) -0.0041(8) -0.0012(9) -0.0031(10) C2 0.0789(17) 0.0540(12) 0.0643(14) -0.0040(10) -0.0201(13) -0.0082(12) C3 0.138(3) 0.0730(17) 0.0679(17) 0.0139(14) -0.021(2) -0.016(2) C4 0.127(3) 0.092(2) 0.082(2) -0.0001(19) 0.032(2) -0.020(2) C5 0.103(3) 0.100(2) 0.097(2) -0.006(2) 0.040(2) -0.001(2) C6 0.0735(16) 0.0665(14) 0.0589(13) -0.0038(12) 0.0059(12) 0.0052(12) C7 0.092(2) 0.106(3) 0.123(3) 0.016(2) 0.012(2) 0.034(2) O2 0.0697(12) 0.0721(12) 0.129(2) 0.0065(14) -0.0234(13) 0.0046(10) S8 0.0825(4) 0.0557(3) 0.0590(3) -0.0045(3) 0.0076(3) -0.0102(3) C9 0.0586(12) 0.0597(12) 0.0462(11) 0.0066(9) 0.0009(9) -0.0002(10) C10 0.0529(11) 0.0546(11) 0.0474(10) 0.0020(8) -0.0043(10) 0.0066(9) C11 0.0535(12) 0.0579(13) 0.0642(14) 0.0050(11) 0.0034(10) -0.0001(10) C12 0.0558(12) 0.0688(13) 0.0592(12) 0.0128(12) 0.0105(10) 0.0039(11) C13 0.0846(18) 0.0859(18) 0.0577(14) -0.0056(13) 0.0086(14) 0.0049(15) C14 0.111(2) 0.0791(18) 0.0705(17) -0.0224(16) -0.0059(18) 0.0041(17) C15 0.106(2) 0.0651(15) 0.0749(18) -0.0085(14) -0.0084(16) -0.0107(15) C16 0.0832(18) 0.0638(14) 0.0649(14) 0.0051(12) -0.0059(13) -0.0113(13) C17 0.0586(12) 0.0562(12) 0.0518(12) 0.0097(10) -0.0067(10) 0.0021(9) C18 0.0542(12) 0.0628(12) 0.0509(11) 0.0073(9) 0.0020(10) 0.0092(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.337(4) . ? C1 C2 1.478(3) . ? C1 S8 1.767(2) . ? C2 O2 1.204(4) . ? C2 C3 1.498(4) . ? C3 C4 1.520(6) . ? C4 C5 1.481(5) . ? C5 C6 1.506(4) . ? C6 C7 1.474(5) . ? S8 C10 1.761(2) . ? C9 C10 1.352(3) . ? C9 C17 1.430(3) . ? C10 C11 1.423(3) . ? C11 C12 1.358(3) . ? C12 C18 1.396(4) . ? C13 C14 1.355(5) . ? C13 C18 1.429(4) . ? C14 C15 1.394(5) . ? C15 C16 1.358(4) . ? C16 C17 1.401(3) . ? C17 C18 1.407(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 122.9(2) . . ? C6 C1 S8 120.75(19) . . ? C2 C1 S8 116.0(2) . . ? O2 C2 C1 122.0(3) . . ? O2 C2 C3 121.3(3) . . ? C1 C2 C3 116.7(3) . . ? C2 C3 C4 113.0(3) . . ? C5 C4 C3 110.9(3) . . ? C4 C5 C6 113.0(3) . . ? C1 C6 C7 124.5(3) . . ? C1 C6 C5 120.4(3) . . ? C7 C6 C5 115.1(3) . . ? C10 S8 C1 104.52(10) . . ? C10 C9 C17 120.6(2) . . ? C9 C10 C11 119.8(2) . . ? C9 C10 S8 125.51(18) . . ? C11 C10 S8 114.63(17) . . ? C12 C11 C10 120.5(2) . . ? C11 C12 C18 120.7(2) . . ? C14 C13 C18 120.1(3) . . ? C13 C14 C15 120.7(3) . . ? C16 C15 C14 120.7(3) . . ? C15 C16 C17 120.4(3) . . ? C16 C17 C18 119.6(2) . . ? C16 C17 C9 121.9(2) . . ? C18 C17 C9 118.5(2) . . ? C12 C18 C17 119.8(2) . . ? C12 C18 C13 121.8(2) . . ? C17 C18 C13 118.4(2) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.385 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.070 #===END data_imai913_2b _database_code_depnum_ccdc_archive 'CCDC 749802' #data_rth2nfb _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H16 O S' _chemical_formula_weight 268.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.7552(6) _cell_length_b 11.0921(7) _cell_length_c 12.3352(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1334.74(15) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 3125 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 28.31 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8836 _exptl_absorpt_correction_T_max 0.9553 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9720 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 28.31 _reflns_number_total 3305 _reflns_number_gt 3125 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.0354P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(6) _refine_ls_number_reflns 3305 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0342 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0842 _refine_ls_wR_factor_gt 0.0835 _refine_ls_goodness_of_fit_ref 1.044 _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 C1 C 0.64804(14) 0.80233(14) 0.64330(12) 0.0290(3) Uani 1 1 d . . . C2 C 0.73334(13) 0.72482(12) 0.57255(10) 0.0226(3) Uani 1 1 d . . . C3 C 0.76868(14) 0.61238(14) 0.60126(12) 0.0284(3) Uani 1 1 d . . . C4 C 0.71419(15) 0.55774(15) 0.70466(13) 0.0366(4) Uani 1 1 d . . . H4A H 0.7808 0.5721 0.7638 0.044 Uiso 1 1 calc R . . H4B H 0.7049 0.4695 0.6950 0.044 Uiso 1 1 calc R . . C5 C 0.57682(16) 0.60975(16) 0.73668(13) 0.0366(4) Uani 1 1 d . . . H5A H 0.5066 0.5860 0.6828 0.044 Uiso 1 1 calc R . . H5B H 0.5491 0.5773 0.8082 0.044 Uiso 1 1 calc R . . C6 C 0.58573(17) 0.74507(17) 0.74233(13) 0.0371(4) Uani 1 1 d . . . H6A H 0.4924 0.7781 0.7528 0.045 Uiso 1 1 calc R . . H6B H 0.6410 0.7677 0.8065 0.045 Uiso 1 1 calc R . . C7 C 0.86497(18) 0.53551(15) 0.53846(17) 0.0469(4) Uani 1 1 d . . . H7A H 0.8870 0.5751 0.4696 0.070 Uiso 1 1 calc R . . H7B H 0.8221 0.4572 0.5240 0.070 Uiso 1 1 calc R . . H7C H 0.9492 0.5235 0.5803 0.070 Uiso 1 1 calc R . . C9 C 0.68858(14) 0.84049(11) 0.26308(11) 0.0233(3) Uani 1 1 d . . . H9 H 0.7542 0.9036 0.2593 0.028 Uiso 1 1 calc R . . C10 C 0.68237(13) 0.76983(11) 0.35408(11) 0.0221(3) Uani 1 1 d . . . C11 C 0.58462(14) 0.67606(12) 0.36037(11) 0.0248(3) Uani 1 1 d . . . H11 H 0.5805 0.6266 0.4232 0.030 Uiso 1 1 calc R . . C12 C 0.49584(14) 0.65624(13) 0.27637(12) 0.0260(3) Uani 1 1 d . . . H12 H 0.4302 0.5933 0.2819 0.031 Uiso 1 1 calc R . . C13 C 0.40988(14) 0.70848(14) 0.09328(12) 0.0285(3) Uani 1 1 d . . . H13 H 0.3442 0.6454 0.0967 0.034 Uiso 1 1 calc R . . C14 C 0.41635(15) 0.77905(14) 0.00395(12) 0.0311(3) Uani 1 1 d . . . H14 H 0.3548 0.7659 -0.0545 0.037 Uiso 1 1 calc R . . C15 C 0.51452(16) 0.87225(13) -0.00241(12) 0.0306(3) Uani 1 1 d . . . H15 H 0.5180 0.9215 -0.0653 0.037 Uiso 1 1 calc R . . C16 C 0.60436(15) 0.89282(13) 0.07995(12) 0.0269(3) Uani 1 1 d . . . H16 H 0.6706 0.9553 0.0739 0.032 Uiso 1 1 calc R . . C17 C 0.59893(13) 0.82090(12) 0.17487(10) 0.0221(3) Uani 1 1 d . . . C18 C 0.49994(13) 0.72748(12) 0.18181(11) 0.0236(3) Uani 1 1 d . . . O1 O 0.63386(12) 0.90898(10) 0.62584(12) 0.0456(3) Uani 1 1 d . . . S8 S 0.80506(4) 0.79576(3) 0.45721(3) 0.02775(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0232(6) 0.0328(7) 0.0310(7) -0.0078(6) -0.0023(5) -0.0035(6) C2 0.0216(6) 0.0285(7) 0.0177(6) 0.0003(5) -0.0019(5) -0.0025(5) C3 0.0236(7) 0.0316(7) 0.0302(7) 0.0029(6) -0.0023(5) -0.0007(5) C4 0.0331(8) 0.0411(9) 0.0356(8) 0.0150(7) -0.0061(6) -0.0025(6) C5 0.0320(7) 0.0545(10) 0.0232(7) 0.0083(7) -0.0008(6) -0.0084(7) C6 0.0319(7) 0.0571(10) 0.0222(7) -0.0097(7) 0.0028(6) -0.0061(7) C7 0.0431(9) 0.0325(8) 0.0653(12) 0.0024(9) 0.0151(9) 0.0071(7) C9 0.0239(6) 0.0222(6) 0.0239(6) -0.0012(5) 0.0040(6) -0.0007(5) C10 0.0216(6) 0.0239(6) 0.0207(6) -0.0031(5) -0.0005(5) 0.0030(5) C11 0.0258(6) 0.0254(7) 0.0231(6) 0.0016(5) 0.0021(5) -0.0011(5) C12 0.0241(6) 0.0273(7) 0.0265(7) -0.0008(5) 0.0027(5) -0.0034(5) C13 0.0239(6) 0.0322(7) 0.0295(7) -0.0052(6) 0.0003(5) -0.0019(6) C14 0.0305(7) 0.0375(8) 0.0251(7) -0.0048(6) -0.0043(6) 0.0028(6) C15 0.0399(8) 0.0298(7) 0.0222(6) 0.0018(6) 0.0006(6) 0.0040(6) C16 0.0318(7) 0.0247(7) 0.0242(6) -0.0003(5) 0.0033(6) 0.0021(5) C17 0.0237(6) 0.0216(6) 0.0209(6) -0.0008(5) 0.0045(5) 0.0035(5) C18 0.0216(6) 0.0250(7) 0.0242(6) -0.0032(5) 0.0046(5) 0.0019(5) O1 0.0349(6) 0.0295(6) 0.0722(9) -0.0097(6) 0.0114(6) 0.0004(5) S8 0.02765(17) 0.03410(19) 0.02149(16) 0.00395(14) -0.00327(13) -0.00763(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.210(2) . ? C1 C2 1.4810(19) . ? C1 C6 1.505(2) . ? C2 C3 1.342(2) . ? C2 S8 1.7699(13) . ? C3 C7 1.486(2) . ? C3 C4 1.509(2) . ? C4 C5 1.511(2) . ? C5 C6 1.505(3) . ? C9 C10 1.3703(18) . ? C9 C17 1.4128(19) . ? C10 C11 1.4132(19) . ? C10 S8 1.7702(13) . ? C11 C12 1.368(2) . ? C12 C18 1.4094(19) . ? C13 C14 1.353(2) . ? C13 C18 1.4174(19) . ? C14 C15 1.411(2) . ? C15 C16 1.361(2) . ? C16 C17 1.4178(19) . ? C17 C18 1.4190(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 121.78(15) . . ? O1 C1 C6 120.72(15) . . ? C2 C1 C6 117.40(14) . . ? C3 C2 C1 121.90(13) . . ? C3 C2 S8 121.60(11) . . ? C1 C2 S8 115.96(11) . . ? C2 C3 C7 123.92(15) . . ? C2 C3 C4 120.40(14) . . ? C7 C3 C4 115.65(14) . . ? C3 C4 C5 112.33(13) . . ? C6 C5 C4 109.97(13) . . ? C1 C6 C5 113.99(14) . . ? C10 C9 C17 121.03(12) . . ? C9 C10 C11 119.72(12) . . ? C9 C10 S8 117.76(10) . . ? C11 C10 S8 122.44(11) . . ? C12 C11 C10 120.25(13) . . ? C11 C12 C18 121.25(12) . . ? C14 C13 C18 120.83(13) . . ? C13 C14 C15 120.05(14) . . ? C16 C15 C14 121.21(14) . . ? C15 C16 C17 119.87(13) . . ? C9 C17 C16 121.76(13) . . ? C9 C17 C18 119.15(12) . . ? C16 C17 C18 119.09(13) . . ? C12 C18 C13 122.46(13) . . ? C12 C18 C17 118.60(12) . . ? C13 C18 C17 118.94(13) . . ? C2 S8 C10 103.78(6) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.297 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.051 #===END data_imai913_3 _database_code_depnum_ccdc_archive 'CCDC 749803' #data_im9270a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H13 N O2 S' _chemical_formula_weight 331.37 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7637(6) _cell_length_b 8.5895(6) _cell_length_c 12.7850(9) _cell_angle_alpha 105.3860(10) _cell_angle_beta 98.5840(10) _cell_angle_gamma 105.8040(10) _cell_volume 768.07(10) _cell_formula_units_Z 2 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 3075 _cell_measurement_theta_min 1.70 _cell_measurement_theta_max 27.92 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.223 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9065 _exptl_absorpt_correction_T_max 0.9674 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 115(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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6801 _diffrn_reflns_av_R_equivalents 0.0156 _diffrn_reflns_av_sigmaI/netI 0.0264 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 27.92 _reflns_number_total 3434 _reflns_number_gt 3075 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.3489P] 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 3434 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1067 _refine_ls_wR_factor_gt 0.1033 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 0.50981(15) -0.02034(15) 0.69926(9) 0.0256(3) Uani 1 1 d . . . O4 O 0.22636(18) 0.28912(15) 0.45042(10) 0.0342(3) Uani 1 1 d . . . C1 C 0.4110(2) 0.03858(19) 0.65047(12) 0.0201(3) Uani 1 1 d . . . C2 C 0.41362(19) 0.21860(19) 0.69818(12) 0.0200(3) Uani 1 1 d . . . C3 C 0.3613(2) 0.30381(19) 0.63145(13) 0.0226(3) Uani 1 1 d . . . C4 C 0.2670(2) 0.2103(2) 0.51109(13) 0.0230(3) Uani 1 1 d . . . C5 C 0.1050(2) -0.0734(2) 0.36427(13) 0.0247(3) Uani 1 1 d . . . H5 H 0.0564 -0.0179 0.3179 0.030 Uiso 1 1 calc R . . C6 C 0.0638(2) -0.2488(2) 0.32673(13) 0.0289(4) Uani 1 1 d . . . H6 H -0.0145 -0.3138 0.2548 0.035 Uiso 1 1 calc R . . C7 C 0.1366(2) -0.3306(2) 0.39363(14) 0.0306(4) Uani 1 1 d . . . H7 H 0.1085 -0.4511 0.3671 0.037 Uiso 1 1 calc R . . C8 C 0.2496(2) -0.2369(2) 0.49855(13) 0.0266(3) Uani 1 1 d . . . H8 H 0.3002 -0.2929 0.5438 0.032 Uiso 1 1 calc R . . C9 C 0.2892(2) -0.06087(19) 0.53792(12) 0.0205(3) Uani 1 1 d . . . C10 C 0.2177(2) 0.02160(19) 0.47016(12) 0.0206(3) Uani 1 1 d . . . C11 C 0.3878(3) 0.4911(2) 0.66911(14) 0.0335(4) Uani 1 1 d . . . H11A H 0.4279 0.5368 0.7508 0.050 Uiso 1 1 calc R . . H11B H 0.2711 0.5091 0.6446 0.050 Uiso 1 1 calc R . . H11C H 0.4816 0.5500 0.6366 0.050 Uiso 1 1 calc R . . S12 S 0.51593(5) 0.32299(5) 0.84132(3) 0.02368(13) Uani 1 1 d . . . N13 N 0.25145(16) 0.04622(15) 0.83822(10) 0.0177(3) Uani 1 1 d . . . C14 C 0.39394(19) 0.17697(18) 0.90144(12) 0.0175(3) Uani 1 1 d . . . C15 C 0.4605(2) 0.21642(18) 1.01795(12) 0.0193(3) Uani 1 1 d . . . H15 H 0.5648 0.3140 1.0589 0.023 Uiso 1 1 calc R . . C16 C 0.3713(2) 0.11104(18) 1.06948(12) 0.0192(3) Uani 1 1 d . . . H16 H 0.4101 0.1358 1.1479 0.023 Uiso 1 1 calc R . . C17 C 0.1245(2) -0.15609(19) 1.05176(13) 0.0214(3) Uani 1 1 d . . . H17 H 0.1592 -0.1376 1.1297 0.026 Uiso 1 1 calc R . . C18 C -0.0177(2) -0.29868(19) 0.98461(14) 0.0237(3) Uani 1 1 d . . . H18 H -0.0811 -0.3791 1.0161 0.028 Uiso 1 1 calc R . . C19 C -0.0702(2) -0.32634(19) 0.86942(13) 0.0243(3) Uani 1 1 d . . . H19 H -0.1687 -0.4259 0.8238 0.029 Uiso 1 1 calc R . . C20 C 0.0181(2) -0.21247(18) 0.82188(12) 0.0207(3) Uani 1 1 d . . . H20 H -0.0193 -0.2329 0.7439 0.025 Uiso 1 1 calc R . . C21 C 0.16512(19) -0.06455(17) 0.88907(12) 0.0170(3) Uani 1 1 d . . . C22 C 0.21948(19) -0.03656(18) 1.00510(12) 0.0174(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0252(6) 0.0348(6) 0.0236(6) 0.0149(5) 0.0070(4) 0.0142(5) O4 0.0484(7) 0.0321(6) 0.0243(6) 0.0148(5) 0.0023(5) 0.0142(6) C1 0.0181(7) 0.0262(7) 0.0196(7) 0.0122(6) 0.0077(5) 0.0064(6) C2 0.0174(7) 0.0225(7) 0.0185(7) 0.0086(6) 0.0046(5) 0.0019(5) C3 0.0246(7) 0.0221(7) 0.0208(7) 0.0100(6) 0.0056(6) 0.0042(6) C4 0.0249(7) 0.0268(8) 0.0200(7) 0.0110(6) 0.0060(6) 0.0091(6) C5 0.0247(8) 0.0325(8) 0.0179(7) 0.0093(6) 0.0058(6) 0.0092(6) C6 0.0286(8) 0.0334(9) 0.0183(8) 0.0039(6) 0.0051(6) 0.0049(7) C7 0.0390(9) 0.0226(8) 0.0268(9) 0.0044(6) 0.0096(7) 0.0073(7) C8 0.0319(8) 0.0264(8) 0.0244(8) 0.0101(6) 0.0081(6) 0.0115(6) C9 0.0209(7) 0.0250(7) 0.0186(7) 0.0090(6) 0.0080(5) 0.0084(6) C10 0.0198(7) 0.0259(8) 0.0187(7) 0.0094(6) 0.0078(5) 0.0075(6) C11 0.0497(11) 0.0216(8) 0.0257(9) 0.0105(7) 0.0023(7) 0.0067(7) S12 0.0250(2) 0.0210(2) 0.0179(2) 0.00809(15) 0.00096(14) -0.00324(14) N13 0.0189(6) 0.0171(6) 0.0164(6) 0.0059(5) 0.0040(5) 0.0042(5) C14 0.0185(6) 0.0172(6) 0.0172(7) 0.0074(5) 0.0048(5) 0.0045(5) C15 0.0203(7) 0.0179(7) 0.0170(7) 0.0033(5) 0.0023(5) 0.0056(5) C16 0.0230(7) 0.0207(7) 0.0148(7) 0.0053(5) 0.0036(5) 0.0095(6) C17 0.0265(7) 0.0242(7) 0.0203(7) 0.0114(6) 0.0095(6) 0.0125(6) C18 0.0261(8) 0.0199(7) 0.0318(8) 0.0139(6) 0.0138(6) 0.0089(6) C19 0.0240(7) 0.0174(7) 0.0290(8) 0.0057(6) 0.0080(6) 0.0037(6) C20 0.0218(7) 0.0186(7) 0.0189(7) 0.0043(6) 0.0040(6) 0.0043(6) C21 0.0178(7) 0.0165(7) 0.0184(7) 0.0059(5) 0.0055(5) 0.0072(5) C22 0.0190(7) 0.0181(7) 0.0179(7) 0.0066(5) 0.0059(5) 0.0088(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2123(18) . ? O4 C4 1.2172(19) . ? C1 C9 1.482(2) . ? C1 C2 1.497(2) . ? C2 C3 1.348(2) . ? C2 S12 1.7582(15) . ? C3 C4 1.496(2) . ? C3 C11 1.497(2) . ? C4 C10 1.483(2) . ? C5 C6 1.382(2) . ? C5 C10 1.391(2) . ? C6 C7 1.391(2) . ? C7 C8 1.381(2) . ? C8 C9 1.390(2) . ? C9 C10 1.399(2) . ? S12 C14 1.7728(14) . ? N13 C14 1.3088(18) . ? N13 C21 1.3741(17) . ? C14 C15 1.417(2) . ? C15 C16 1.358(2) . ? C16 C22 1.420(2) . ? C17 C18 1.371(2) . ? C17 C22 1.4135(19) . ? C18 C19 1.405(2) . ? C19 C20 1.368(2) . ? C20 C21 1.4117(19) . ? C21 C22 1.416(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C9 121.61(14) . . ? O1 C1 C2 121.64(14) . . ? C9 C1 C2 116.67(13) . . ? C3 C2 C1 121.04(14) . . ? C3 C2 S12 121.17(12) . . ? C1 C2 S12 117.26(11) . . ? C2 C3 C4 120.06(14) . . ? C2 C3 C11 124.60(14) . . ? C4 C3 C11 115.34(13) . . ? O4 C4 C10 121.67(14) . . ? O4 C4 C3 119.66(14) . . ? C10 C4 C3 118.60(13) . . ? C6 C5 C10 119.83(15) . . ? C5 C6 C7 120.37(15) . . ? C8 C7 C6 120.11(15) . . ? C7 C8 C9 120.00(15) . . ? C8 C9 C10 119.87(14) . . ? C8 C9 C1 119.61(14) . . ? C10 C9 C1 120.50(14) . . ? C5 C10 C9 119.81(14) . . ? C5 C10 C4 120.70(14) . . ? C9 C10 C4 119.47(13) . . ? C2 S12 C14 101.59(7) . . ? C14 N13 C21 116.73(12) . . ? N13 C14 C15 125.29(13) . . ? N13 C14 S12 119.43(11) . . ? C15 C14 S12 115.27(10) . . ? C16 C15 C14 118.21(13) . . ? C15 C16 C22 119.40(13) . . ? C18 C17 C22 120.00(14) . . ? C17 C18 C19 120.25(13) . . ? C20 C19 C18 121.15(14) . . ? C19 C20 C21 119.79(14) . . ? N13 C21 C20 118.13(13) . . ? N13 C21 C22 122.54(13) . . ? C20 C21 C22 119.32(13) . . ? C17 C22 C21 119.48(13) . . ? C17 C22 C16 122.77(13) . . ? C21 C22 C16 117.74(13) . . ? _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 27.92 _diffrn_measured_fraction_theta_full 0.931 _refine_diff_density_max 0.450 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.059 #===END data_imai913_4 _database_code_depnum_ccdc_archive 'CCDC 749804' #data_th2nf8n _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H15 N O S' _chemical_formula_weight 269.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.6159(5) _cell_length_b 10.3651(7) _cell_length_c 17.2948(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1365.24(16) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3143 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 28.29 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9044 _exptl_absorpt_correction_T_max 0.9732 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10197 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 28.29 _reflns_number_total 3379 _reflns_number_gt 3143 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.07(5) _refine_ls_number_reflns 3379 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0323 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0762 _refine_ls_wR_factor_gt 0.0754 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 0.39769(13) 0.10192(9) 0.41508(6) 0.0270(2) Uani 1 1 d . . . C1 C 0.26883(17) 0.17146(12) 0.41266(7) 0.0208(3) Uani 1 1 d . . . C2 C 0.10361(18) 0.13322(12) 0.37339(7) 0.0207(3) Uani 1 1 d . . . C3 C -0.02322(17) 0.21985(14) 0.35681(7) 0.0229(3) Uani 1 1 d . . . C4 C -0.00285(19) 0.36104(14) 0.37625(8) 0.0255(3) Uani 1 1 d . . . H4A H -0.0768 0.3810 0.4218 0.031 Uiso 1 1 calc R . . H4B H -0.0470 0.4130 0.3323 0.031 Uiso 1 1 calc R . . C5 C 0.18481(18) 0.40108(14) 0.39351(9) 0.0270(3) Uani 1 1 d . . . H5A H 0.1859 0.4882 0.4170 0.032 Uiso 1 1 calc R . . H5B H 0.2532 0.4043 0.3449 0.032 Uiso 1 1 calc R . . C6 C 0.26823(19) 0.30413(14) 0.44913(8) 0.0265(3) Uani 1 1 d . . . H6A H 0.3901 0.3308 0.4611 0.032 Uiso 1 1 calc R . . H6B H 0.2010 0.3020 0.4981 0.032 Uiso 1 1 calc R . . C7 C -0.1952(2) 0.18635(17) 0.31915(9) 0.0343(3) Uani 1 1 d . . . H7A H -0.1999 0.0933 0.3094 0.051 Uiso 1 1 calc R . . H7B H -0.2058 0.2329 0.2701 0.051 Uiso 1 1 calc R . . H7C H -0.2920 0.2110 0.3534 0.051 Uiso 1 1 calc R . . S8 S 0.08287(5) -0.03061(3) 0.345105(19) 0.02558(9) Uani 1 1 d . . . N9 N 0.08385(14) -0.04293(10) 0.49975(6) 0.0205(2) Uani 1 1 d . . . C10 C 0.06348(18) -0.10931(12) 0.43561(7) 0.0213(3) Uani 1 1 d . . . C11 C 0.02613(19) -0.24410(13) 0.43234(8) 0.0269(3) Uani 1 1 d . . . H11 H 0.0094 -0.2864 0.3842 0.032 Uiso 1 1 calc R . . C12 C 0.0152(2) -0.31048(13) 0.50003(8) 0.0274(3) Uani 1 1 d . . . H12 H -0.0104 -0.4002 0.4996 0.033 Uiso 1 1 calc R . . C13 C 0.03951(17) -0.30887(13) 0.64385(8) 0.0274(3) Uani 1 1 d . . . H13 H 0.0197 -0.3993 0.6463 0.033 Uiso 1 1 calc R . . C14 C 0.06563(19) -0.24038(14) 0.71055(8) 0.0285(3) Uani 1 1 d . . . H14 H 0.0655 -0.2838 0.7589 0.034 Uiso 1 1 calc R . . C15 C 0.09264(19) -0.10603(14) 0.70795(8) 0.0262(3) Uani 1 1 d . . . H15 H 0.1083 -0.0593 0.7547 0.031 Uiso 1 1 calc R . . C16 C 0.09649(17) -0.04197(13) 0.63850(7) 0.0228(3) Uani 1 1 d . . . H16 H 0.1148 0.0487 0.6374 0.027 Uiso 1 1 calc R . . C17 C 0.07320(17) -0.11085(12) 0.56830(7) 0.0194(2) Uani 1 1 d . . . C18 C 0.04197(16) -0.24547(12) 0.57111(8) 0.0222(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0253(5) 0.0244(5) 0.0311(5) 0.0010(4) -0.0004(4) 0.0043(4) C1 0.0230(6) 0.0206(6) 0.0186(6) 0.0032(5) 0.0022(5) -0.0002(5) C2 0.0244(7) 0.0198(6) 0.0178(5) 0.0004(5) 0.0017(5) -0.0017(5) C3 0.0225(6) 0.0270(7) 0.0193(7) 0.0025(5) 0.0024(5) 0.0002(5) C4 0.0257(7) 0.0240(7) 0.0267(7) 0.0039(6) 0.0026(5) 0.0066(6) C5 0.0263(7) 0.0193(7) 0.0353(8) -0.0013(6) 0.0039(6) 0.0016(5) C6 0.0236(7) 0.0240(7) 0.0318(7) -0.0050(6) -0.0025(5) 0.0003(6) C7 0.0274(8) 0.0394(9) 0.0359(8) 0.0008(7) -0.0076(6) 0.0003(6) S8 0.03678(19) 0.02067(15) 0.01929(15) -0.00190(13) 0.00093(14) -0.00343(14) N9 0.0221(5) 0.0180(5) 0.0213(5) -0.0003(4) 0.0019(4) -0.0011(5) C10 0.0230(7) 0.0188(6) 0.0222(6) -0.0002(5) 0.0027(5) -0.0003(5) C11 0.0356(8) 0.0206(6) 0.0244(7) -0.0054(5) 0.0035(6) -0.0038(6) C12 0.0336(7) 0.0165(6) 0.0321(7) -0.0025(6) 0.0075(6) -0.0045(5) C13 0.0283(7) 0.0227(6) 0.0312(8) 0.0036(6) 0.0053(6) -0.0022(5) C14 0.0271(7) 0.0327(8) 0.0255(7) 0.0075(6) 0.0019(6) -0.0003(6) C15 0.0224(7) 0.0336(7) 0.0226(6) -0.0026(5) -0.0015(6) -0.0003(6) C16 0.0207(6) 0.0227(6) 0.0251(6) -0.0021(5) 0.0004(5) -0.0026(5) C17 0.0167(6) 0.0187(6) 0.0229(6) 0.0006(5) 0.0021(5) 0.0006(5) C18 0.0200(7) 0.0196(6) 0.0272(7) 0.0002(5) 0.0037(5) -0.0012(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2184(16) . ? C1 C2 1.4838(18) . ? C1 C6 1.5129(19) . ? C2 C3 1.3496(19) . ? C2 S8 1.7742(13) . ? C3 C7 1.5035(19) . ? C3 C4 1.5096(19) . ? C4 C5 1.518(2) . ? C5 C6 1.529(2) . ? S8 C10 1.7713(13) . ? N9 C10 1.3145(16) . ? N9 C17 1.3813(16) . ? C10 C11 1.4269(18) . ? C11 C12 1.3605(19) . ? C12 C18 1.4166(19) . ? C13 C14 1.369(2) . ? C13 C18 1.4194(19) . ? C14 C15 1.408(2) . ? C15 C16 1.3727(18) . ? C16 C17 1.4196(18) . ? C17 C18 1.4163(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 122.74(12) . . ? O1 C1 C6 121.73(12) . . ? C2 C1 C6 115.53(11) . . ? C3 C2 C1 121.77(12) . . ? C3 C2 S8 120.96(10) . . ? C1 C2 S8 117.22(9) . . ? C2 C3 C7 124.19(13) . . ? C2 C3 C4 121.61(12) . . ? C7 C3 C4 114.20(12) . . ? C3 C4 C5 113.93(12) . . ? C4 C5 C6 109.58(12) . . ? C1 C6 C5 109.65(11) . . ? C10 S8 C2 101.80(6) . . ? C10 N9 C17 116.79(11) . . ? N9 C10 C11 124.72(12) . . ? N9 C10 S8 119.66(10) . . ? C11 C10 S8 115.63(10) . . ? C12 C11 C10 118.24(13) . . ? C11 C12 C18 119.83(12) . . ? C14 C13 C18 120.32(13) . . ? C13 C14 C15 120.46(13) . . ? C16 C15 C14 120.62(12) . . ? C15 C16 C17 120.16(12) . . ? N9 C17 C16 118.07(11) . . ? N9 C17 C18 122.78(12) . . ? C16 C17 C18 119.15(12) . . ? C13 C18 C17 119.26(13) . . ? C13 C18 C12 123.16(12) . . ? C17 C18 C12 117.58(12) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.284 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.044 #===END