#------------------------------------------------------------------------------ #$Date: 2021-09-17 03:23:46 +0300 (Fri, 17 Sep 2021) $ #$Revision: 269171 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158305.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7158305 loop_ _publ_author_name 'Zhang, Shan-Shan' 'Xue, Jiahui' 'Gu, Qing' 'Jiang, Xuefeng' 'You, Shuli' _publ_section_title ; Dearomatization Reaction of \b Naphthols with Disulfurating Reagents ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB01731D _journal_year 2021 _chemical_formula_moiety 'C20 H20 O S2' _chemical_formula_sum 'C20 H20 O S2' _chemical_formula_weight 340.48 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2020-07-17 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-06-22 deposited with the CCDC. 2021-09-16 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.794(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.8031(5) _cell_length_b 12.4858(6) _cell_length_c 14.4741(8) _cell_measurement_reflns_used 9964 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 54.96 _cell_measurement_theta_min 3.99 _cell_volume 1740.28(16) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 173.0 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type GaK\a _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_unetI/netI 0.0250 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 19615 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 54.954 _diffrn_reflns_theta_min 3.994 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.803 _exptl_absorpt_correction_T_max 0.7508 _exptl_absorpt_correction_T_min 0.5383 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1260 before and 0.0579 after correction. The Ratio of minimum to maximum transmission is 0.7170. The \l/2 correction factor is Not present.' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.300 _exptl_crystal_description block _exptl_crystal_F_000 720 _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.889 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.056 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 211 _refine_ls_number_reflns 3294 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.053 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0407 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+1.4247P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1097 _refine_ls_wR_factor_ref 0.1107 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3161 _reflns_number_total 3294 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01731d2.cif _cod_data_source_block mj20384_0m _cod_database_code 7158305 _shelx_shelxl_version_number 2016/6 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.915 _shelx_estimated_absorpt_t_min 0.869 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C12(H12A,H12B) 2.b Aromatic/amide H refined with riding coordinates: C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C17(H17), C18(H18) 2.c Idealised Me refined as rotating group: C11(H11A,H11B,H11C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C) ; _shelx_res_file ; TITL mj20384_0m_a.res in P2(1)/c mj20384_0m.res created by SHELXL-2016/6 at 09:46:42 on 17-Jul-2020 REM Old TITL mj20384_0m in P21/c #14 REM SHELXT solution in P2(1)/c REM R1 0.123, Rweak 0.006, Alpha 0.021, Orientation as input REM Formula found by SHELXT: C20 O S2 CELL 1.34139 9.8031 12.4858 14.4741 90 100.794 90 ZERR 4 0.0005 0.0006 0.0008 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H O S DISP C 0.0148 0.007 57.7477 DISP H -0 0 0.6481 DISP O 0.0412 0.025 193.9543 DISP S 0.2924 0.4247 3241.7632 UNIT 80 80 4 8 L.S. 8 PLAN 20 SIZE 0.05 0.06 0.08 TEMP -100.15 BOND $H list 4 fmap 2 ACTA REM REM REM WGHT 0.052000 1.424700 FVAR 0.66767 S1 4 0.428353 0.349954 0.424763 11.00000 0.03021 0.02536 = 0.04504 0.00156 0.01229 -0.00030 S2 4 0.571744 0.418089 0.359626 11.00000 0.03560 0.03794 = 0.03410 0.00923 0.00348 -0.00958 O1 3 0.665909 0.165313 0.393603 11.00000 0.03854 0.04233 = 0.04805 -0.00131 0.02548 0.00466 C1 1 0.428514 0.200706 0.400238 11.00000 0.02989 0.02527 = 0.03154 -0.00123 0.00781 -0.00267 C2 1 0.576403 0.166791 0.441945 11.00000 0.02852 0.02213 = 0.03921 -0.00500 0.01382 -0.00049 C3 1 0.611054 0.140798 0.543533 11.00000 0.02396 0.02432 = 0.03910 -0.00451 0.00751 -0.00023 C4 1 0.507816 0.125340 0.590940 11.00000 0.02788 0.03291 = 0.02982 -0.00082 0.00484 0.00061 AFIX 43 H4 2 0.531771 0.108278 0.655925 11.00000 -1.20000 AFIX 0 C5 1 0.361660 0.133044 0.549173 11.00000 0.02443 0.02359 = 0.03471 -0.00270 0.00674 -0.00063 C6 1 0.261387 0.105609 0.602150 11.00000 0.03199 0.03032 = 0.03683 0.00087 0.01269 -0.00070 AFIX 43 H6 2 0.289789 0.084218 0.665839 11.00000 -1.20000 AFIX 0 C7 1 0.122316 0.109133 0.563437 11.00000 0.02851 0.02877 = 0.05387 -0.00023 0.01857 -0.00227 AFIX 43 H7 2 0.055283 0.089511 0.600017 11.00000 -1.20000 AFIX 0 C8 1 0.080365 0.141222 0.471375 11.00000 0.02116 0.02867 = 0.05996 -0.00018 0.00520 -0.00119 AFIX 43 H8 2 -0.015758 0.144252 0.444645 11.00000 -1.20000 AFIX 0 C9 1 0.178367 0.169153 0.417574 11.00000 0.03039 0.02843 = 0.04174 0.00309 0.00139 0.00036 AFIX 43 H9 2 0.148459 0.191362 0.354241 11.00000 -1.20000 AFIX 0 C10 1 0.319660 0.165036 0.455183 11.00000 0.02503 0.02062 = 0.03547 -0.00124 0.00823 -0.00079 C11 1 0.395025 0.179740 0.295405 11.00000 0.05318 0.04341 = 0.03217 -0.00397 0.01065 -0.00646 AFIX 137 H11A 2 0.307672 0.215408 0.268196 11.00000 -1.50000 H11B 2 0.385717 0.102463 0.284112 11.00000 -1.50000 H11C 2 0.470006 0.207776 0.266047 11.00000 -1.50000 AFIX 0 C12 1 0.729476 0.426016 0.450222 11.00000 0.03380 0.03747 = 0.03196 0.00215 0.00428 -0.00704 AFIX 23 H12A 2 0.713536 0.472432 0.502631 11.00000 -1.20000 H12B 2 0.756390 0.353847 0.475590 11.00000 -1.20000 AFIX 0 C13 1 0.842113 0.472365 0.404361 11.00000 0.02927 0.03101 = 0.02881 0.00031 0.00356 -0.00320 C14 1 0.863203 0.581763 0.401337 11.00000 0.02863 0.03030 = 0.03933 -0.00508 0.00888 -0.00044 AFIX 43 H14 2 0.804640 0.629013 0.427502 11.00000 -1.20000 AFIX 0 C15 1 0.969055 0.623072 0.360458 11.00000 0.03231 0.02652 = 0.03954 -0.00297 0.00810 -0.00398 AFIX 43 H15 2 0.981728 0.698449 0.359073 11.00000 -1.20000 AFIX 0 C16 1 1.056838 0.556824 0.321549 11.00000 0.03064 0.03744 = 0.02858 0.00047 0.00599 -0.00158 C17 1 1.033746 0.447287 0.323184 11.00000 0.04367 0.03544 = 0.04237 -0.00091 0.01681 0.00767 AFIX 43 H17 2 1.091409 0.400147 0.296110 11.00000 -1.20000 AFIX 0 C18 1 0.927911 0.405563 0.363681 11.00000 0.04679 0.02583 = 0.04507 0.00079 0.01370 0.00173 AFIX 43 H18 2 0.913729 0.330295 0.363671 11.00000 -1.20000 AFIX 0 C19 1 1.174743 0.602195 0.279985 11.00000 0.04229 0.04914 = 0.04541 -0.00118 0.02179 -0.00403 AFIX 137 H19A 2 1.173046 0.680563 0.283366 11.00000 -1.50000 H19B 2 1.164420 0.579838 0.214138 11.00000 -1.50000 H19C 2 1.263298 0.575637 0.315472 11.00000 -1.50000 AFIX 0 C20 1 0.760834 0.124758 0.585346 11.00000 0.02442 0.03762 = 0.05446 -0.00175 0.00575 0.00082 AFIX 137 H20A 2 0.797481 0.064548 0.554048 11.00000 -1.50000 H20B 2 0.770434 0.109326 0.652641 11.00000 -1.50000 H20C 2 0.812891 0.189872 0.576791 11.00000 -1.50000 AFIX 0 HKLF 4 REM mj20384_0m_a.res in P2(1)/c REM R1 = 0.0407 for 3161 Fo > 4sig(Fo) and 0.0420 for all 3294 data REM 211 parameters refined using 0 restraints END WGHT 0.0520 1.4247 REM Highest difference peak 0.889, deepest hole -0.243, 1-sigma level 0.056 Q1 1 0.7044 0.3949 0.5097 11.00000 0.05 0.89 Q2 1 0.5155 0.3338 0.5223 11.00000 0.05 0.85 Q3 1 0.3703 0.1788 0.4294 11.00000 0.05 0.30 Q4 1 0.4963 0.1845 0.4181 11.00000 0.05 0.29 Q5 1 0.3489 0.1448 0.4983 11.00000 0.05 0.29 Q6 1 0.1258 0.1251 0.4308 11.00000 0.05 0.26 Q7 1 0.8616 0.4463 0.3659 11.00000 0.05 0.25 Q8 1 0.6709 0.4391 0.3919 11.00000 0.05 0.24 Q9 1 0.1169 0.1071 0.5129 11.00000 0.05 0.24 Q10 1 0.4364 0.2666 0.4099 11.00000 0.05 0.24 Q11 1 0.3086 0.1230 0.5734 11.00000 0.05 0.24 Q12 1 0.2628 0.1503 0.4328 11.00000 0.05 0.24 Q13 1 0.7935 0.4572 0.4210 11.00000 0.05 0.24 Q14 1 0.4215 0.1340 0.5675 11.00000 0.05 0.23 Q15 1 0.6782 0.1374 0.5688 11.00000 0.05 0.23 Q16 1 1.0156 0.5921 0.3334 11.00000 0.05 0.23 Q17 1 1.1186 0.5769 0.3104 11.00000 0.05 0.23 Q18 1 1.0348 0.5097 0.3197 11.00000 0.05 0.22 Q19 1 0.8343 0.5281 0.3841 11.00000 0.05 0.21 Q20 1 0.9084 0.6010 0.3659 11.00000 0.05 0.21 ; _shelx_res_checksum 32002 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.42835(5) 0.34995(4) 0.42476(4) 0.03286(15) Uani 1 1 d . . . . . S2 S 0.57174(5) 0.41809(4) 0.35963(3) 0.03627(16) Uani 1 1 d . . . . . O1 O 0.66591(15) 0.16531(12) 0.39360(11) 0.0407(4) Uani 1 1 d . . . . . C1 C 0.42851(19) 0.20071(15) 0.40024(13) 0.0286(4) Uani 1 1 d . . . . . C2 C 0.57640(19) 0.16679(15) 0.44194(14) 0.0290(4) Uani 1 1 d . . . . . C3 C 0.61105(19) 0.14080(15) 0.54353(14) 0.0289(4) Uani 1 1 d . . . . . C4 C 0.50782(19) 0.12534(16) 0.59094(13) 0.0303(4) Uani 1 1 d . . . . . H4 H 0.531771 0.108278 0.655925 0.036 Uiso 1 1 calc R . . . . C5 C 0.36166(19) 0.13304(15) 0.54917(13) 0.0274(4) Uani 1 1 d . . . . . C6 C 0.2614(2) 0.10561(16) 0.60215(14) 0.0322(4) Uani 1 1 d . . . . . H6 H 0.289789 0.084218 0.665839 0.039 Uiso 1 1 calc R . . . . C7 C 0.1223(2) 0.10913(16) 0.56344(16) 0.0356(5) Uani 1 1 d . . . . . H7 H 0.055283 0.089511 0.600017 0.043 Uiso 1 1 calc R . . . . C8 C 0.0804(2) 0.14122(16) 0.47138(16) 0.0369(5) Uani 1 1 d . . . . . H8 H -0.015758 0.144252 0.444645 0.044 Uiso 1 1 calc R . . . . C9 C 0.1784(2) 0.16915(16) 0.41757(15) 0.0342(4) Uani 1 1 d . . . . . H9 H 0.148459 0.191362 0.354241 0.041 Uiso 1 1 calc R . . . . C10 C 0.31966(19) 0.16504(14) 0.45518(13) 0.0267(4) Uani 1 1 d . . . . . C11 C 0.3950(3) 0.17974(19) 0.29540(14) 0.0426(5) Uani 1 1 d . . . . . H11A H 0.307672 0.215408 0.268196 0.064 Uiso 1 1 calc GR . . . . H11B H 0.385717 0.102463 0.284112 0.064 Uiso 1 1 calc GR . . . . H11C H 0.470006 0.207776 0.266047 0.064 Uiso 1 1 calc GR . . . . C12 C 0.7295(2) 0.42602(17) 0.45022(14) 0.0347(4) Uani 1 1 d . . . . . H12A H 0.713536 0.472432 0.502631 0.042 Uiso 1 1 calc R . . . . H12B H 0.756390 0.353847 0.475590 0.042 Uiso 1 1 calc R . . . . C13 C 0.8421(2) 0.47236(16) 0.40436(13) 0.0299(4) Uani 1 1 d . . . . . C14 C 0.8632(2) 0.58176(16) 0.40134(14) 0.0324(4) Uani 1 1 d . . . . . H14 H 0.804640 0.629013 0.427502 0.039 Uiso 1 1 calc R . . . . C15 C 0.9691(2) 0.62307(16) 0.36046(14) 0.0326(4) Uani 1 1 d . . . . . H15 H 0.981728 0.698449 0.359073 0.039 Uiso 1 1 calc R . . . . C16 C 1.0568(2) 0.55682(17) 0.32155(13) 0.0322(4) Uani 1 1 d . . . . . C17 C 1.0337(2) 0.44729(18) 0.32318(15) 0.0394(5) Uani 1 1 d . . . . . H17 H 1.091409 0.400147 0.296110 0.047 Uiso 1 1 calc R . . . . C18 C 0.9279(2) 0.40556(17) 0.36368(16) 0.0386(5) Uani 1 1 d . . . . . H18 H 0.913729 0.330295 0.363671 0.046 Uiso 1 1 calc R . . . . C19 C 1.1747(2) 0.6022(2) 0.27999(16) 0.0439(5) Uani 1 1 d . . . . . H19A H 1.173046 0.680563 0.283366 0.066 Uiso 1 1 calc GR . . . . H19B H 1.164420 0.579838 0.214138 0.066 Uiso 1 1 calc GR . . . . H19C H 1.263298 0.575637 0.315472 0.066 Uiso 1 1 calc GR . . . . C20 C 0.7608(2) 0.12476(18) 0.58535(17) 0.0390(5) Uani 1 1 d . . . . . H20A H 0.797481 0.064548 0.554048 0.059 Uiso 1 1 calc GR . . . . H20B H 0.770434 0.109326 0.652641 0.059 Uiso 1 1 calc GR . . . . H20C H 0.812891 0.189872 0.576791 0.059 Uiso 1 1 calc GR . . . . 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 S1 0.0302(3) 0.0254(3) 0.0450(3) 0.00156(19) 0.0123(2) -0.00030(18) S2 0.0356(3) 0.0379(3) 0.0341(3) 0.0092(2) 0.0035(2) -0.0096(2) O1 0.0385(8) 0.0423(9) 0.0481(9) -0.0013(7) 0.0255(7) 0.0047(6) C1 0.0299(10) 0.0253(9) 0.0315(9) -0.0012(7) 0.0078(7) -0.0027(7) C2 0.0285(10) 0.0221(9) 0.0392(10) -0.0050(8) 0.0138(8) -0.0005(7) C3 0.0240(9) 0.0243(9) 0.0391(10) -0.0045(8) 0.0075(8) -0.0002(7) C4 0.0279(10) 0.0329(10) 0.0298(9) -0.0008(8) 0.0048(7) 0.0006(8) C5 0.0244(9) 0.0236(9) 0.0347(10) -0.0027(7) 0.0067(7) -0.0006(7) C6 0.0320(10) 0.0303(10) 0.0368(10) 0.0009(8) 0.0127(8) -0.0007(8) C7 0.0285(10) 0.0288(10) 0.0539(13) -0.0002(9) 0.0186(9) -0.0023(8) C8 0.0212(9) 0.0287(10) 0.0600(13) -0.0002(9) 0.0052(9) -0.0012(8) C9 0.0304(10) 0.0284(10) 0.0417(11) 0.0031(8) 0.0014(8) 0.0004(8) C10 0.0250(9) 0.0206(9) 0.0355(10) -0.0012(7) 0.0082(7) -0.0008(7) C11 0.0532(13) 0.0434(12) 0.0322(11) -0.0040(9) 0.0107(9) -0.0065(10) C12 0.0338(10) 0.0375(11) 0.0320(10) 0.0021(8) 0.0043(8) -0.0070(8) C13 0.0293(9) 0.0310(10) 0.0288(9) 0.0003(8) 0.0036(7) -0.0032(8) C14 0.0286(10) 0.0303(10) 0.0393(10) -0.0051(8) 0.0089(8) -0.0004(8) C15 0.0323(10) 0.0265(10) 0.0395(11) -0.0030(8) 0.0081(8) -0.0040(8) C16 0.0306(10) 0.0374(11) 0.0286(9) 0.0005(8) 0.0060(8) -0.0016(8) C17 0.0437(12) 0.0354(11) 0.0424(11) -0.0009(9) 0.0168(9) 0.0077(9) C18 0.0468(12) 0.0258(10) 0.0451(12) 0.0008(8) 0.0137(10) 0.0017(9) C19 0.0423(12) 0.0491(13) 0.0454(12) -0.0012(10) 0.0218(10) -0.0040(10) C20 0.0244(10) 0.0376(11) 0.0545(13) -0.0018(10) 0.0057(9) 0.0008(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0148 0.0070 '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 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.2924 0.4247 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 S2 107.53(6) . . ? C12 S2 S1 104.84(7) . . ? C2 C1 S1 103.48(12) . . ? C10 C1 S1 99.52(12) . . ? C10 C1 C2 115.02(16) . . ? C10 C1 C11 115.73(17) . . ? C11 C1 S1 110.47(14) . . ? C11 C1 C2 111.16(17) . . ? O1 C2 C1 120.69(18) . . ? O1 C2 C3 120.65(18) . . ? C3 C2 C1 118.60(15) . . ? C2 C3 C20 117.18(17) . . ? C4 C3 C2 119.04(17) . . ? C4 C3 C20 123.59(19) . . ? C3 C4 H4 118.0 . . ? C3 C4 C5 124.02(18) . . ? C5 C4 H4 118.0 . . ? C6 C5 C4 119.76(17) . . ? C6 C5 C10 119.52(17) . . ? C10 C5 C4 120.70(17) . . ? C5 C6 H6 119.5 . . ? C7 C6 C5 120.95(19) . . ? C7 C6 H6 119.5 . . ? C6 C7 H7 120.1 . . ? C6 C7 C8 119.81(18) . . ? C8 C7 H7 120.1 . . ? C7 C8 H8 119.9 . . ? C7 C8 C9 120.15(18) . . ? C9 C8 H8 119.9 . . ? C8 C9 H9 119.5 . . ? C8 C9 C10 120.91(19) . . ? C10 C9 H9 119.5 . . ? C5 C10 C1 119.06(16) . . ? C9 C10 C1 122.16(17) . . ? C9 C10 C5 118.66(17) . . ? C1 C11 H11A 109.5 . . ? C1 C11 H11B 109.5 . . ? C1 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? S2 C12 H12A 110.3 . . ? S2 C12 H12B 110.3 . . ? H12A C12 H12B 108.5 . . ? C13 C12 S2 107.17(13) . . ? C13 C12 H12A 110.3 . . ? C13 C12 H12B 110.3 . . ? C14 C13 C12 121.30(18) . . ? C14 C13 C18 118.22(18) . . ? C18 C13 C12 120.49(18) . . ? C13 C14 H14 119.7 . . ? C13 C14 C15 120.60(18) . . ? C15 C14 H14 119.7 . . ? C14 C15 H15 119.3 . . ? C14 C15 C16 121.48(19) . . ? C16 C15 H15 119.3 . . ? C15 C16 C17 117.74(18) . . ? C15 C16 C19 121.17(19) . . ? C17 C16 C19 121.09(19) . . ? C16 C17 H17 119.5 . . ? C18 C17 C16 121.03(19) . . ? C18 C17 H17 119.5 . . ? C13 C18 H18 119.5 . . ? C17 C18 C13 120.91(19) . . ? C17 C18 H18 119.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C3 C20 H20A 109.5 . . ? C3 C20 H20B 109.5 . . ? C3 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? 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 S1 S2 2.0211(7) . ? S1 C1 1.897(2) . ? S2 C12 1.833(2) . ? O1 C2 1.221(2) . ? C1 C2 1.522(3) . ? C1 C10 1.512(3) . ? C1 C11 1.514(3) . ? C2 C3 1.482(3) . ? C3 C4 1.339(3) . ? C3 C20 1.493(3) . ? C4 H4 0.9500 . ? C4 C5 1.450(3) . ? C5 C6 1.398(3) . ? C5 C10 1.404(3) . ? C6 H6 0.9500 . ? C6 C7 1.374(3) . ? C7 H7 0.9500 . ? C7 C8 1.378(3) . ? C8 H8 0.9500 . ? C8 C9 1.390(3) . ? C9 H9 0.9500 . ? C9 C10 1.391(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C12 C13 1.506(3) . ? C13 C14 1.383(3) . ? C13 C18 1.391(3) . ? C14 H14 0.9500 . ? C14 C15 1.387(3) . ? C15 H15 0.9500 . ? C15 C16 1.387(3) . ? C16 C17 1.387(3) . ? C16 C19 1.510(3) . ? C17 H17 0.9500 . ? C17 C18 1.385(3) . ? C18 H18 0.9500 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ?