# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Gareth J. Rowlands' 'Rakesh Parmar' _publ_contact_author_name 'Dr Gareth J Rowlands' _publ_contact_author_address ; Department of Chemistry University of Sussex Falmer Brighton Sussex BN1 9QJ UNITED KINGDOM ; _publ_contact_author_email G.ROWLANDS@SUSSEX.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; The facile synthesis of enantiomerically pure 4-substituted [2.2]paracyclophanes ; _publ_requested_category FO data_jun1704 _database_code_depnum_ccdc_archive 'CCDC 276960' _audit_creation_date 2004-06-16T11:16:09-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C23 H22 O1 S1' _chemical_formula_sum 'C23 H22 O1 S1' _chemical_formula_weight 346.47 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.4226(2) _cell_length_b 11.4979(2) _cell_length_c 14.9892(2) _cell_angle_alpha 90 _cell_angle_beta 95.392(1) _cell_angle_gamma 90 _cell_volume 1788.33(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 23802 _cell_measurement_theta_min 3.705 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.188 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.116699E-1 _diffrn_orient_matrix_ub_12 0.6673E-2 _diffrn_orient_matrix_ub_13 0.667882E-1 _diffrn_orient_matrix_ub_21 0.95621E-1 _diffrn_orient_matrix_ub_22 -0.33735E-2 _diffrn_orient_matrix_ub_23 -0.16505E-2 _diffrn_orient_matrix_ub_31 0.2824E-2 _diffrn_orient_matrix_ub_32 0.866504E-1 _diffrn_orient_matrix_ub_33 -0.52076E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.051 _diffrn_reflns_av_unetI/netI 0.0298 _diffrn_reflns_number 40001 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.8 _diffrn_reflns_theta_max 25.05 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 6305 _reflns_number_gt 5866 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; The H atoms were refined, with the exception of that on C16b which had to be put in riding mode. The reason is that there appers to a very slight contamination by a product with a substituent at C16b. This is evidenced by a residual peak of ca. 1 electron at a distance of 1.54 angstroms from C16b. 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^)+(0.0637P)^2^+0.5005P] 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_number_reflns 6305 _refine_ls_number_parameters 623 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0936 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.994 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(5) _refine_diff_density_max 1.001 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.04 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' 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 S S 0.10309(6) 0.00386(5) 0.20488(4) 0.02900(15) Uani 1 1 d . . . O O 0.0720(2) -0.07700(16) 0.12797(11) 0.0398(4) Uani 1 1 d . . . C1 C -0.1629(3) -0.2373(2) 0.18054(19) 0.0396(7) Uani 1 1 d . . . H1B H -0.113(3) -0.235(3) 0.123(2) 0.054(9) Uiso 1 1 d . . . H1A H -0.250(3) -0.272(3) 0.1689(19) 0.039(7) Uiso 1 1 d . . . C2 C -0.1885(3) -0.1074(2) 0.20958(19) 0.0349(6) Uani 1 1 d . . . H2B H -0.167(3) -0.058(3) 0.159(2) 0.036(7) Uiso 1 1 d . . . H2A H -0.285(3) -0.105(2) 0.2229(17) 0.028(7) Uiso 1 1 d . . . C3 C -0.1091(2) -0.0721(2) 0.29445(15) 0.0258(5) Uani 1 1 d . . . C4 C 0.0211(2) -0.0414(2) 0.29885(15) 0.0241(5) Uani 1 1 d . . . C5 C 0.1028(2) -0.0611(2) 0.37634(16) 0.0266(5) Uani 1 1 d . . . H5 H 0.201(3) -0.054(2) 0.3713(17) 0.025(6) Uiso 1 1 d . . . C6 C 0.0563(3) -0.1093(2) 0.45189(16) 0.0311(6) Uani 1 1 d . . . C7 C -0.0764(3) -0.1110(2) 0.45404(17) 0.0344(6) Uani 1 1 d . . . H7 H -0.115(3) -0.134(3) 0.505(2) 0.046(8) Uiso 1 1 d . . . C8 C -0.1570(3) -0.0938(2) 0.37666(17) 0.0301(5) Uani 1 1 d . . . H8 H -0.250(3) -0.107(3) 0.379(2) 0.043(8) Uiso 1 1 d . . . C9 C 0.1432(3) -0.1759(3) 0.51998(18) 0.0416(7) Uani 1 1 d . . . H9A H 0.120(3) -0.156(3) 0.581(2) 0.048(9) Uiso 1 1 d . . . H9B H 0.236(3) -0.154(2) 0.5150(18) 0.029(7) Uiso 1 1 d . . . C10 C 0.1311(4) -0.3131(3) 0.5068(2) 0.0502(8) Uani 1 1 d . . . H10B H 0.218(4) -0.333(3) 0.511(2) 0.060(10) Uiso 1 1 d . . . H10A H 0.081(3) -0.344(3) 0.560(2) 0.055(9) Uiso 1 1 d . . . C11 C 0.0626(3) -0.3450(2) 0.41649(18) 0.0353(6) Uani 1 1 d . . . C12 C 0.1216(3) -0.3271(2) 0.33827(18) 0.0340(6) Uani 1 1 d . . . H12 H 0.223(3) -0.312(3) 0.3487(18) 0.038(7) Uiso 1 1 d . . . C13 C 0.0486(2) -0.3069(2) 0.25761(17) 0.0311(6) Uani 1 1 d . . . H13 H 0.086(3) -0.282(3) 0.204(2) 0.040(8) Uiso 1 1 d . . . C14 C -0.0862(2) -0.3057(2) 0.25343(17) 0.0318(6) Uani 1 1 d . . . C15 C -0.1422(3) -0.3502(2) 0.32625(19) 0.0364(6) Uani 1 1 d . . . H15 H -0.238(3) -0.356(3) 0.3240(18) 0.034(7) Uiso 1 1 d . . . C16 C -0.0687(3) -0.3691(2) 0.4070(2) 0.0389(6) Uani 1 1 d . . . H16 H -0.107(3) -0.386(3) 0.455(2) 0.039(8) Uiso 1 1 d . . . C17 C 0.0182(2) 0.1374(2) 0.17593(15) 0.0254(5) Uani 1 1 d . . . C18 C -0.0239(2) 0.1555(2) 0.08639(16) 0.0282(5) Uani 1 1 d . . . H18 H -0.018(3) 0.090(3) 0.0459(19) 0.039(8) Uiso 1 1 d . . . C19 C -0.0722(2) 0.2632(2) 0.05900(16) 0.0273(5) Uani 1 1 d . . . H19 H -0.097(2) 0.274(2) -0.0057(17) 0.027(6) Uiso 1 1 d . . . C20 C -0.0792(2) 0.3539(2) 0.11985(16) 0.0288(5) Uani 1 1 d . . . C21 C -0.0366(3) 0.3329(2) 0.21037(17) 0.0311(5) Uani 1 1 d . . . H21 H -0.043(3) 0.402(3) 0.249(2) 0.049(8) Uiso 1 1 d . . . C22 C 0.0122(2) 0.2260(2) 0.23801(16) 0.0307(5) Uani 1 1 d . . . H22 H 0.043(2) 0.210(2) 0.3016(18) 0.030(7) Uiso 1 1 d . . . C23 C -0.1307(3) 0.4702(3) 0.0890(2) 0.0395(7) Uani 1 1 d . . . H23C H -0.072(6) 0.528(6) 0.102(4) 0.14(2) Uiso 1 1 d . . . H23B H -0.151(4) 0.476(4) 0.023(3) 0.075(12) Uiso 1 1 d . . . H23A H -0.204(5) 0.493(4) 0.116(3) 0.090(13) Uiso 1 1 d . . . S1B S 0.68771(5) -0.21439(5) 0.63062(4) 0.02811(15) Uani 1 1 d . . . O1B O 0.68328(18) -0.34073(17) 0.65371(12) 0.0393(4) Uani 1 1 d . . . C1B C 0.4071(3) -0.3479(3) 0.7806(2) 0.0454(7) Uani 1 1 d . . . H1X H 0.447(4) -0.412(4) 0.762(3) 0.075(13) Uiso 1 1 d . . . H1Y H 0.316(4) -0.360(4) 0.796(3) 0.086(13) Uiso 1 1 d . . . C2B C 0.3969(3) -0.2638(3) 0.69633(19) 0.0355(6) Uani 1 1 d . . . H2Y H 0.308(3) -0.242(3) 0.679(2) 0.042(8) Uiso 1 1 d . . . H2X H 0.426(3) -0.305(3) 0.6453(19) 0.034(7) Uiso 1 1 d . . . C3B C 0.4655(2) -0.1498(2) 0.71462(15) 0.0266(5) Uani 1 1 d . . . C4B C 0.5956(2) -0.1295(2) 0.70213(14) 0.0248(5) Uani 1 1 d . . . C5B C 0.6688(3) -0.0497(2) 0.75401(16) 0.0286(5) Uani 1 1 d . . . H5B H 0.753(3) -0.042(3) 0.7487(19) 0.035(8) Uiso 1 1 d . . . C6B C 0.6142(3) 0.0157(2) 0.81927(16) 0.0324(6) Uani 1 1 d . . . C7B C 0.4807(3) 0.0163(2) 0.81514(16) 0.0357(6) Uani 1 1 d . . . H7B H 0.434(3) 0.071(3) 0.8563(19) 0.039(7) Uiso 1 1 d . . . C8B C 0.4085(3) -0.0644(2) 0.76410(17) 0.0329(6) Uani 1 1 d . . . H8B H 0.315(3) -0.077(3) 0.768(2) 0.050(9) Uiso 1 1 d . . . C9B C 0.6949(4) 0.0642(3) 0.89981(19) 0.0469(7) Uani 1 1 d . . . H9Y H 0.666(4) 0.144(4) 0.920(2) 0.068(11) Uiso 1 1 d . . . H9X H 0.784(3) 0.082(3) 0.887(2) 0.053(9) Uiso 1 1 d . . . C10B C 0.7045(4) -0.0209(3) 0.9834(2) 0.0489(8) Uani 1 1 d . . . H10Y H 0.661(4) 0.032(4) 1.031(3) 0.089(13) Uiso 1 1 d . . . H10X H 0.796(4) -0.029(3) 1.004(2) 0.061(10) Uiso 1 1 d . . . C11B C 0.6358(3) -0.1346(2) 0.96368(16) 0.0339(6) Uani 1 1 d . . . C12B C 0.6944(2) -0.2202(3) 0.91590(16) 0.0350(6) Uani 1 1 d . . . H12B H 0.788(3) -0.218(3) 0.9110(19) 0.042(8) Uiso 1 1 d . . . C13B C 0.6214(2) -0.3011(2) 0.86482(17) 0.0341(6) Uani 1 1 d . . . H13B H 0.663(3) -0.356(3) 0.822(2) 0.039(7) Uiso 1 1 d . . . C14B C 0.4873(2) -0.2984(2) 0.86089(17) 0.0341(6) Uani 1 1 d . . . C15B C 0.4327(2) -0.2309(3) 0.92450(17) 0.0364(6) Uani 1 1 d . . . H15B H 0.338(3) -0.232(3) 0.9289(17) 0.035(7) Uiso 1 1 d . . . C16B C 0.5063(3) -0.1491(3) 0.97569(17) 0.0390(7) Uani 1 1 d . . . H16B H 0.4678 -0.1034 1.0187 0.047 Uiso 1 1 calc R . . C17B C 0.5918(2) -0.1979(2) 0.52520(15) 0.0261(5) Uani 1 1 d . . . C18B C 0.5767(2) -0.2950(2) 0.47042(16) 0.0296(5) Uani 1 1 d . . . H18B H 0.612(2) -0.376(3) 0.4981(18) 0.031(7) Uiso 1 1 d . . . C19B C 0.5165(2) -0.2838(2) 0.38406(17) 0.0313(5) Uani 1 1 d . . . H24 H 0.512(3) -0.353(3) 0.3482(19) 0.038(7) Uiso 1 1 d . . . C20B C 0.4727(2) -0.1765(2) 0.35090(16) 0.0288(5) Uani 1 1 d . . . C21B C 0.4876(2) -0.0802(2) 0.40766(17) 0.0325(6) Uani 1 1 d . . . H21B H 0.466(3) 0.003(3) 0.384(2) 0.058(9) Uiso 1 1 d . . . C22B C 0.5475(2) -0.0900(2) 0.49411(16) 0.0302(5) Uani 1 1 d . . . H22B H 0.560(3) -0.016(3) 0.5309(19) 0.041(8) Uiso 1 1 d . . . C23B C 0.4138(3) -0.1643(3) 0.25548(19) 0.0398(6) Uani 1 1 d . . . H23Y H 0.353(4) -0.230(4) 0.242(3) 0.074(12) Uiso 1 1 d . . . H23X H 0.369(4) -0.093(4) 0.248(3) 0.071(11) Uiso 1 1 d . . . H23Z H 0.488(5) -0.168(4) 0.218(3) 0.089(14) Uiso 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 S 0.0321(3) 0.0298(3) 0.0261(3) 0.0033(3) 0.0084(2) 0.0025(3) O 0.0627(12) 0.0311(10) 0.0271(9) -0.0009(8) 0.0114(8) 0.0050(9) C1 0.0429(16) 0.0330(16) 0.0396(15) -0.0046(12) -0.0133(12) -0.0002(13) C2 0.0322(14) 0.0334(15) 0.0373(14) 0.0021(12) -0.0055(11) 0.0021(11) C3 0.0263(12) 0.0204(12) 0.0305(12) 0.0002(10) 0.0009(10) 0.0036(10) C4 0.0282(11) 0.0205(11) 0.0242(11) -0.0005(9) 0.0060(9) 0.0018(9) C5 0.0308(13) 0.0213(13) 0.0270(12) -0.0024(10) 0.0000(10) -0.0021(10) C6 0.0452(15) 0.0243(13) 0.0234(12) -0.0041(10) 0.0013(10) -0.0003(11) C7 0.0508(16) 0.0271(13) 0.0276(13) -0.0009(11) 0.0151(12) -0.0039(12) C8 0.0300(13) 0.0232(13) 0.0384(14) -0.0042(11) 0.0102(11) -0.0010(10) C9 0.0576(18) 0.0399(16) 0.0255(14) 0.0025(12) -0.0052(13) -0.0054(14) C10 0.067(2) 0.0419(19) 0.0388(17) 0.0068(14) -0.0101(15) 0.0065(16) C11 0.0458(15) 0.0223(12) 0.0364(14) 0.0036(11) -0.0034(12) 0.0046(11) C12 0.0350(14) 0.0264(13) 0.0401(15) -0.0020(11) 0.0012(11) 0.0027(11) C13 0.0378(14) 0.0248(13) 0.0311(13) -0.0070(11) 0.0056(11) 0.0006(10) C14 0.0375(13) 0.0216(13) 0.0352(14) -0.0073(10) -0.0025(11) -0.0001(10) C15 0.0347(14) 0.0260(13) 0.0479(16) -0.0025(12) 0.0009(12) -0.0014(11) C16 0.0508(17) 0.0251(14) 0.0426(16) 0.0034(12) 0.0139(13) 0.0004(12) C17 0.0244(11) 0.0280(13) 0.0240(11) 0.0023(10) 0.0030(9) -0.0021(10) C18 0.0304(13) 0.0312(13) 0.0233(12) -0.0033(11) 0.0041(9) -0.0058(11) C19 0.0290(12) 0.0306(14) 0.0227(12) 0.0017(10) 0.0048(9) -0.0016(10) C20 0.0274(12) 0.0291(14) 0.0306(13) 0.0021(10) 0.0068(10) -0.0022(10) C21 0.0362(13) 0.0290(14) 0.0290(12) -0.0028(11) 0.0078(10) -0.0039(11) C22 0.0335(13) 0.0353(14) 0.0232(12) -0.0002(11) 0.0031(10) -0.0031(12) C23 0.0525(18) 0.0309(15) 0.0372(15) 0.0077(12) 0.0144(14) 0.0077(13) S1B 0.0270(3) 0.0312(3) 0.0259(3) -0.0033(3) 0.0017(2) 0.0033(3) O1B 0.0505(11) 0.0324(10) 0.0341(10) -0.0026(8) -0.0009(8) 0.0094(9) C1B 0.0500(18) 0.0406(18) 0.0444(17) 0.0041(14) -0.0022(14) -0.0105(15) C2B 0.0284(14) 0.0394(15) 0.0379(15) -0.0016(12) -0.0010(11) -0.0026(12) C3B 0.0274(11) 0.0314(13) 0.0208(11) 0.0052(10) 0.0007(9) 0.0040(10) C4B 0.0281(12) 0.0249(12) 0.0213(11) 0.0031(9) 0.0007(9) 0.0041(10) C5B 0.0326(14) 0.0269(13) 0.0261(12) 0.0069(10) 0.0014(10) -0.0042(11) C6B 0.0520(15) 0.0200(12) 0.0252(12) 0.0014(10) 0.0034(11) -0.0035(11) C7B 0.0532(16) 0.0299(14) 0.0251(12) 0.0042(11) 0.0101(11) 0.0082(13) C8B 0.0351(14) 0.0381(15) 0.0258(12) 0.0101(11) 0.0039(11) 0.0073(12) C9B 0.069(2) 0.0416(18) 0.0299(15) -0.0076(13) 0.0047(14) -0.0189(16) C10B 0.0594(19) 0.053(2) 0.0322(15) -0.0026(14) -0.0071(14) -0.0069(16) C11B 0.0402(14) 0.0395(15) 0.0208(12) 0.0054(11) -0.0033(10) -0.0009(12) C12B 0.0310(13) 0.0431(15) 0.0301(12) 0.0112(13) -0.0016(10) 0.0037(13) C13B 0.0371(14) 0.0301(14) 0.0352(14) 0.0105(11) 0.0039(11) 0.0057(11) C14B 0.0349(13) 0.0327(15) 0.0348(14) 0.0129(11) 0.0034(11) -0.0041(11) C15B 0.0304(13) 0.0433(16) 0.0363(13) 0.0162(12) 0.0078(11) 0.0044(12) C16B 0.0476(16) 0.0480(17) 0.0225(12) 0.0090(12) 0.0087(11) 0.0092(13) C17B 0.0243(11) 0.0296(14) 0.0251(11) -0.0013(10) 0.0067(9) 0.0001(10) C18B 0.0343(13) 0.0268(13) 0.0277(12) 0.0020(10) 0.0034(10) -0.0019(11) C19B 0.0328(13) 0.0288(14) 0.0324(13) -0.0067(11) 0.0039(10) -0.0024(12) C20B 0.0237(11) 0.0336(14) 0.0294(12) 0.0012(10) 0.0046(10) 0.0001(10) C21B 0.0315(13) 0.0309(14) 0.0355(13) 0.0010(11) 0.0053(10) 0.0048(11) C22B 0.0342(13) 0.0289(13) 0.0278(12) -0.0038(11) 0.0051(10) 0.0025(11) C23B 0.0417(16) 0.0443(17) 0.0321(15) 0.0024(13) -0.0034(13) 0.0003(15) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 S O 1.4927(19) . ? S C4 1.792(2) . ? S C17 1.804(2) . ? C1 C14 1.512(4) . ? C1 C2 1.586(4) . ? C2 C3 1.507(3) . ? C3 C8 1.395(4) . ? C3 C4 1.398(3) . ? C4 C5 1.392(3) . ? C5 C6 1.388(4) . ? C6 C7 1.387(4) . ? C6 C9 1.508(4) . ? C7 C8 1.381(4) . ? C9 C10 1.593(5) . ? C10 C11 1.515(4) . ? C11 C12 1.390(4) . ? C11 C16 1.390(4) . ? C12 C13 1.387(4) . ? C13 C14 1.400(4) . ? C14 C15 1.383(4) . ? C15 C16 1.387(4) . ? C17 C22 1.385(4) . ? C17 C18 1.388(3) . ? C18 C19 1.384(4) . ? C19 C20 1.392(4) . ? C20 C21 1.408(4) . ? C20 C23 1.498(4) . ? C21 C22 1.379(4) . ? S1B O1B 1.495(2) . ? S1B C4B 1.793(2) . ? S1B C17B 1.799(2) . ? C1B C14B 1.511(4) . ? C1B C2B 1.587(4) . ? C2B C3B 1.505(4) . ? C3B C8B 1.396(4) . ? C3B C4B 1.406(3) . ? C4B C5B 1.385(3) . ? C5B C6B 1.396(4) . ? C6B C7B 1.387(4) . ? C6B C9B 1.512(4) . ? C7B C8B 1.380(4) . ? C9B C10B 1.586(4) . ? C10B C11B 1.507(4) . ? C11B C16B 1.388(4) . ? C11B C12B 1.392(4) . ? C12B C13B 1.386(4) . ? C13B C14B 1.394(4) . ? C14B C15B 1.392(4) . ? C15B C16B 1.397(4) . ? C17B C18B 1.386(3) . ? C17B C22B 1.388(4) . ? C18B C19B 1.391(3) . ? C19B C20B 1.391(4) . ? C20B C21B 1.396(4) . ? C20B C23B 1.509(4) . ? C21B C22B 1.389(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O S C4 109.96(11) . . ? O S C17 106.16(11) . . ? C4 S C17 100.20(10) . . ? C14 C1 C2 112.5(2) . . ? C3 C2 C1 113.1(2) . . ? C8 C3 C4 115.5(2) . . ? C8 C3 C2 118.9(2) . . ? C4 C3 C2 124.2(2) . . ? C5 C4 C3 120.8(2) . . ? C5 C4 S 113.82(17) . . ? C3 C4 S 124.66(18) . . ? C6 C5 C4 120.8(2) . . ? C7 C6 C5 116.8(2) . . ? C7 C6 C9 120.9(2) . . ? C5 C6 C9 121.4(2) . . ? C8 C7 C6 120.5(2) . . ? C7 C8 C3 121.8(2) . . ? C6 C9 C10 112.6(2) . . ? C11 C10 C9 112.1(2) . . ? C12 C11 C16 116.9(2) . . ? C12 C11 C10 120.6(3) . . ? C16 C11 C10 121.1(3) . . ? C13 C12 C11 120.7(2) . . ? C12 C13 C14 120.5(2) . . ? C15 C14 C13 117.2(2) . . ? C15 C14 C1 121.9(2) . . ? C13 C14 C1 119.8(2) . . ? C14 C15 C16 120.4(3) . . ? C15 C16 C11 121.1(3) . . ? C22 C17 C18 120.6(2) . . ? C22 C17 S 121.10(18) . . ? C18 C17 S 117.61(19) . . ? C19 C18 C17 119.6(2) . . ? C18 C19 C20 121.0(2) . . ? C19 C20 C21 118.2(2) . . ? C19 C20 C23 120.4(2) . . ? C21 C20 C23 121.4(2) . . ? C22 C21 C20 121.1(2) . . ? C21 C22 C17 119.5(2) . . ? O1B S1B C4B 111.14(11) . . ? O1B S1B C17B 106.21(11) . . ? C4B S1B C17B 100.54(10) . . ? C14B C1B C2B 113.2(2) . . ? C3B C2B C1B 113.0(2) . . ? C8B C3B C4B 114.7(2) . . ? C8B C3B C2B 119.4(2) . . ? C4B C3B C2B 124.6(2) . . ? C5B C4B C3B 121.5(2) . . ? C5B C4B S1B 113.52(18) . . ? C3B C4B S1B 124.50(19) . . ? C4B C5B C6B 120.7(2) . . ? C7B C6B C5B 116.4(2) . . ? C7B C6B C9B 120.9(2) . . ? C5B C6B C9B 121.7(3) . . ? C8B C7B C6B 120.9(2) . . ? C7B C8B C3B 122.1(2) . . ? C6B C9B C10B 113.1(2) . . ? C11B C10B C9B 112.7(2) . . ? C16B C11B C12B 117.4(3) . . ? C16B C11B C10B 121.9(3) . . ? C12B C11B C10B 119.4(3) . . ? C13B C12B C11B 120.9(2) . . ? C12B C13B C14B 120.3(3) . . ? C15B C14B C13B 117.2(2) . . ? C15B C14B C1B 121.6(3) . . ? C13B C14B C1B 120.2(3) . . ? C14B C15B C16B 120.8(2) . . ? C11B C16B C15B 120.0(3) . . ? C18B C17B C22B 120.3(2) . . ? C18B C17B S1B 117.25(19) . . ? C22B C17B S1B 121.94(18) . . ? C17B C18B C19B 119.5(2) . . ? C18B C19B C20B 121.3(2) . . ? C19B C20B C21B 118.2(2) . . ? C19B C20B C23B 120.8(2) . . ? C21B C20B C23B 121.0(2) . . ? C22B C21B C20B 121.2(2) . . ? C17B C22B C21B 119.5(2) . . ? #===END data_jun804 _database_code_depnum_ccdc_archive 'CCDC 276961' _audit_creation_date 2004-06-08T11:42:13-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C23 H22 O1 S1' _chemical_formula_sum 'C23 H22 O1 S1' _chemical_formula_weight 346.47 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 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 8.1055(2) _cell_length_b 14.4647(4) _cell_length_c 15.2330(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1785.97(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9886 _cell_measurement_theta_min 3.705 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.189 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.220475E-1 _diffrn_orient_matrix_ub_12 0.676525E-1 _diffrn_orient_matrix_ub_13 0.67133E-2 _diffrn_orient_matrix_ub_21 0.343753E-1 _diffrn_orient_matrix_ub_22 0.103712E-1 _diffrn_orient_matrix_ub_23 -0.622734E-1 _diffrn_orient_matrix_ub_31 -0.116418 _diffrn_orient_matrix_ub_32 -0.97498E-2 _diffrn_orient_matrix_ub_33 -0.196592E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_unetI/netI 0.024 _diffrn_reflns_number 16069 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.78 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _reflns_number_total 3137 _reflns_number_gt 3032 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0450P)^2^+0.4582P] 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 refall _refine_ls_extinction_method none _refine_ls_number_reflns 3137 _refine_ls_number_parameters 314 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0277 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_ref 0.0686 _refine_ls_wR_factor_gt 0.0672 _refine_ls_goodness_of_fit_ref 0.944 _refine_ls_restrained_S_all 0.944 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(6) _refine_diff_density_max 0.165 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.034 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' 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 S S 0.25956(5) 0.97508(2) 0.31057(2) 0.02251(11) Uani 1 1 d . . . O O 0.12610(14) 1.00784(8) 0.37095(8) 0.0308(3) Uani 1 1 d . . . C1 C 0.2474(2) 0.93920(11) 0.07770(10) 0.0279(3) Uani 1 1 d . . . H1B H 0.287(2) 0.9370(13) 0.0180(13) 0.030(5) Uiso 1 1 d . . . H1A H 0.257(2) 1.0023(13) 0.0992(11) 0.026(4) Uiso 1 1 d . . . C2 C 0.3704(2) 0.87834(12) 0.13476(11) 0.0258(4) Uani 1 1 d . . . H2A H 0.455(2) 0.9188(11) 0.1607(10) 0.018(4) Uiso 1 1 d . . . H2B H 0.430(3) 0.8374(14) 0.0935(13) 0.038(5) Uiso 1 1 d . . . C3 C 0.28099(17) 0.82108(10) 0.20345(10) 0.0212(3) Uani 1 1 d . . . C4 C 0.20511(18) 0.85985(10) 0.27702(10) 0.0201(3) Uani 1 1 d . . . C5 C 0.06851(19) 0.81957(10) 0.31586(10) 0.0222(3) Uani 1 1 d . . . H5 H 0.004(2) 0.8558(13) 0.3556(12) 0.026(5) Uiso 1 1 d . . . C6 C 0.0063(2) 0.73606(11) 0.28419(11) 0.0245(3) Uani 1 1 d . . . C7 C 0.1052(2) 0.68687(11) 0.22524(11) 0.0255(4) Uani 1 1 d . . . H7 H 0.064(2) 0.6235(14) 0.2013(13) 0.036(5) Uiso 1 1 d . . . C8 C 0.2397(2) 0.72925(10) 0.18553(11) 0.0254(3) Uani 1 1 d . . . H8 H 0.288(2) 0.6997(13) 0.1388(13) 0.028(5) Uiso 1 1 d . . . C9 C -0.1736(2) 0.71204(13) 0.29701(13) 0.0313(4) Uani 1 1 d . . . H9B H -0.183(2) 0.6451(15) 0.3058(13) 0.040(5) Uiso 1 1 d . . . H9A H -0.212(3) 0.7453(14) 0.3483(13) 0.035(5) Uiso 1 1 d . . . C10 C -0.2848(2) 0.74303(15) 0.21764(15) 0.0388(4) Uani 1 1 d . . . H10B H -0.324(3) 0.6880(18) 0.1846(16) 0.062(7) Uiso 1 1 d . . . H10A H -0.382(3) 0.7709(15) 0.2434(15) 0.050(6) Uiso 1 1 d . . . C11 C -0.19754(19) 0.80808(12) 0.15557(11) 0.0292(4) Uani 1 1 d . . . C12 C -0.1705(2) 0.90041(12) 0.17820(12) 0.0284(4) Uani 1 1 d . . . H12 H -0.239(2) 0.9311(13) 0.2289(13) 0.034(5) Uiso 1 1 d . . . C13 C -0.0382(2) 0.94871(11) 0.14315(11) 0.0259(4) Uani 1 1 d . . . H13 H -0.011(2) 1.0103(13) 0.1683(12) 0.026(4) Uiso 1 1 d . . . C14 C 0.0709(2) 0.90662(11) 0.08454(10) 0.0256(4) Uani 1 1 d . . . C15 C 0.0202(2) 0.82304(13) 0.04786(12) 0.0305(4) Uani 1 1 d . . . H15 H 0.087(3) 0.7944(13) 0.0050(13) 0.036(5) Uiso 1 1 d . . . C16 C -0.1113(2) 0.77434(13) 0.08334(12) 0.0324(4) Uani 1 1 d . . . H16 H -0.134(2) 0.7105(14) 0.0672(12) 0.033(5) Uiso 1 1 d . . . C17 C 0.4355(2) 0.94654(10) 0.37711(10) 0.0214(3) Uani 1 1 d . . . C18 C 0.5769(2) 0.99893(11) 0.36585(11) 0.0268(4) Uani 1 1 d . . . H18 H 0.581(2) 1.0458(13) 0.3206(13) 0.030(5) Uiso 1 1 d . . . C19 C 0.7140(2) 0.98261(12) 0.41851(12) 0.0300(4) Uani 1 1 d . . . H19 H 0.816(3) 1.0162(14) 0.4113(13) 0.034(5) Uiso 1 1 d . . . C20 C 0.7105(2) 0.91466(11) 0.48308(11) 0.0274(4) Uani 1 1 d . . . C21 C 0.5669(2) 0.86276(12) 0.49296(11) 0.0300(4) Uani 1 1 d . . . H21 H 0.564(3) 0.8138(16) 0.5398(15) 0.047(6) Uiso 1 1 d . . . C22 C 0.4301(2) 0.87795(12) 0.44067(11) 0.0295(4) Uani 1 1 d . . . H22 H 0.335(2) 0.8427(13) 0.4479(12) 0.029(5) Uiso 1 1 d . . . C23 C 0.8566(3) 0.89906(17) 0.54219(15) 0.0404(5) Uani 1 1 d . . . H23C H 0.885(4) 0.839(3) 0.537(2) 0.110(12) Uiso 1 1 d . . . H23B H 0.850(4) 0.928(2) 0.594(2) 0.080(9) Uiso 1 1 d . . . H23A H 0.960(5) 0.928(3) 0.517(2) 0.114(12) Uiso 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 S 0.0257(2) 0.01875(18) 0.02307(19) -0.00087(14) -0.00380(17) 0.00020(17) O 0.0282(6) 0.0307(6) 0.0334(6) -0.0110(5) -0.0030(5) 0.0049(5) C1 0.0302(9) 0.0313(8) 0.0222(8) 0.0039(6) 0.0016(8) 0.0011(8) C2 0.0185(8) 0.0323(9) 0.0264(8) -0.0024(7) 0.0037(7) 0.0000(7) C3 0.0164(7) 0.0249(7) 0.0224(7) 0.0008(6) -0.0041(6) 0.0030(6) C4 0.0212(8) 0.0196(7) 0.0194(7) 0.0012(6) -0.0054(6) 0.0010(6) C5 0.0251(8) 0.0242(8) 0.0173(7) 0.0006(7) -0.0019(7) 0.0027(7) C6 0.0252(8) 0.0225(8) 0.0258(8) 0.0051(7) -0.0020(7) -0.0015(6) C7 0.0254(8) 0.0201(8) 0.0310(9) -0.0006(7) -0.0063(7) 0.0000(7) C8 0.0234(8) 0.0250(7) 0.0278(8) -0.0041(7) -0.0028(8) 0.0074(7) C9 0.0279(9) 0.0293(9) 0.0368(10) 0.0022(8) 0.0032(8) -0.0053(7) C10 0.0223(9) 0.0403(10) 0.0538(12) 0.0067(9) -0.0017(8) -0.0059(8) C11 0.0156(7) 0.0364(9) 0.0357(9) 0.0044(7) -0.0070(7) 0.0018(7) C12 0.0201(8) 0.0349(9) 0.0303(9) 0.0030(7) -0.0018(7) 0.0078(7) C13 0.0256(8) 0.0256(8) 0.0264(8) 0.0043(7) -0.0047(7) 0.0056(7) C14 0.0261(8) 0.0314(9) 0.0193(8) 0.0060(6) -0.0028(7) 0.0037(7) C15 0.0270(9) 0.0391(10) 0.0256(9) -0.0061(8) -0.0045(7) 0.0056(8) C16 0.0251(9) 0.0341(10) 0.0381(10) -0.0059(8) -0.0112(8) 0.0004(7) C17 0.0231(8) 0.0213(7) 0.0200(8) -0.0031(6) -0.0009(6) 0.0007(6) C18 0.0283(9) 0.0244(8) 0.0277(9) -0.0001(7) 0.0027(7) -0.0028(7) C19 0.0214(8) 0.0322(9) 0.0363(9) -0.0042(7) 0.0030(7) -0.0050(7) C20 0.0244(8) 0.0306(8) 0.0272(8) -0.0099(7) -0.0032(7) 0.0042(7) C21 0.0318(9) 0.0310(9) 0.0272(9) 0.0038(7) -0.0028(8) -0.0011(8) C22 0.0269(9) 0.0303(9) 0.0314(9) 0.0044(7) -0.0030(7) -0.0098(8) C23 0.0300(10) 0.0501(12) 0.0412(12) -0.0098(10) -0.0093(9) 0.0075(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 S O 1.4969(12) . ? S C17 1.7978(16) . ? S C4 1.7984(15) . ? C1 C14 1.510(2) . ? C1 C2 1.589(2) . ? C2 C3 1.519(2) . ? C3 C4 1.396(2) . ? C3 C8 1.397(2) . ? C4 C5 1.384(2) . ? C5 C6 1.395(2) . ? C6 C7 1.398(2) . ? C6 C9 1.512(2) . ? C7 C8 1.390(2) . ? C9 C10 1.573(3) . ? C10 C11 1.510(3) . ? C11 C16 1.392(3) . ? C11 C12 1.397(3) . ? C12 C13 1.386(3) . ? C13 C14 1.396(2) . ? C14 C15 1.394(2) . ? C15 C16 1.387(3) . ? C17 C18 1.384(2) . ? C17 C22 1.387(2) . ? C18 C19 1.390(2) . ? C19 C20 1.391(2) . ? C20 C21 1.393(2) . ? C20 C23 1.505(3) . ? C21 C22 1.383(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 O S C17 107.44(7) . . ? O S C4 106.90(7) . . ? C17 S C4 98.18(7) . . ? C14 C1 C2 112.59(13) . . ? C3 C2 C1 112.30(13) . . ? C4 C3 C8 115.69(14) . . ? C4 C3 C2 122.98(14) . . ? C8 C3 C2 119.89(14) . . ? C5 C4 C3 121.78(14) . . ? C5 C4 S 117.71(11) . . ? C3 C4 S 119.49(12) . . ? C4 C5 C6 120.38(15) . . ? C5 C6 C7 117.10(15) . . ? C5 C6 C9 120.19(16) . . ? C7 C6 C9 121.27(15) . . ? C8 C7 C6 120.33(14) . . ? C7 C8 C3 121.49(15) . . ? C6 C9 C10 112.83(15) . . ? C11 C10 C9 112.97(15) . . ? C16 C11 C12 116.84(16) . . ? C16 C11 C10 120.78(17) . . ? C12 C11 C10 121.00(17) . . ? C13 C12 C11 120.55(16) . . ? C12 C13 C14 121.08(15) . . ? C15 C14 C13 116.60(16) . . ? C15 C14 C1 121.49(15) . . ? C13 C14 C1 120.55(15) . . ? C16 C15 C14 120.71(17) . . ? C15 C16 C11 121.05(17) . . ? C18 C17 C22 120.28(15) . . ? C18 C17 S 117.47(12) . . ? C22 C17 S 122.18(13) . . ? C17 C18 C19 119.80(16) . . ? C18 C19 C20 120.78(15) . . ? C19 C20 C21 118.31(15) . . ? C19 C20 C23 120.88(17) . . ? C21 C20 C23 120.79(17) . . ? C22 C21 C20 121.46(16) . . ? C21 C22 C17 119.37(16) . . ? #===END