#------------------------------------------------------------------------------ #$Date: 2025-02-01 03:45:13 +0200 (Sat, 01 Feb 2025) $ #$Revision: 297556 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/38/1573821.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_1573821 _journal_paper_doi 10.1039/D5OB00022J _chemical_formula_moiety 'C15 H14 O3 S2' _chemical_formula_sum 'C15 H14 O3 S2' _chemical_formula_weight 306.38 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2024-05-21 _audit_creation_method ; Olex2 1.5-beta (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439) ; _audit_update_record ; 2024-11-15 deposited with the CCDC. 2025-01-31 downloaded from the CCDC. ; _cell_angle_alpha 82.619(4) _cell_angle_beta 74.785(5) _cell_angle_gamma 73.760(5) _cell_formula_units_Z 2 _cell_length_a 6.1960(3) _cell_length_b 10.6217(6) _cell_length_c 11.3470(6) _cell_measurement_reflns_used 3667 _cell_measurement_temperature 149.99(10) _cell_measurement_theta_max 73.4280 _cell_measurement_theta_min 4.0030 _cell_volume 690.62(7) _computing_cell_refinement 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 1.5-beta (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-beta (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 149.99(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2684 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.963 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 2.00 82.00 1.00 1.00 -- 40.73 -99.00 120.00 80 2 \w 43.00 117.00 1.00 1.00 -- 107.58-125.00 0.00 74 3 \w 45.00 135.00 1.00 1.00 -- 107.58 -61.00 30.00 90 4 \w 112.00 153.00 1.00 1.00 -- 107.58 45.00 120.00 41 5 \w 32.00 135.00 1.00 1.00 -- 107.58 -30.00 150.00 103 6 \w -18.00 30.00 1.00 1.00 -- -40.73 57.00-180.00 48 7 \w 141.00 178.00 1.00 1.00 -- 107.58 45.00-180.00 37 8 \w 100.00 128.00 1.00 1.00 -- 107.58 125.00-180.00 28 9 \w 92.00 131.00 1.00 1.00 -- 107.58 45.00-180.00 39 10 \w -84.00 -16.00 1.00 1.00 -- -40.73 -38.00-120.00 68 11 \w -114.00 -86.00 1.00 1.00 -- -40.73 -38.00-120.00 28 12 \w -106.00 -15.00 1.00 1.00 -- -40.98 -57.00 0.00 91 13 \w -28.00 -2.00 1.00 1.00 -- -40.98 125.00 60.00 26 14 \w -28.00 -2.00 1.00 1.00 -- 40.98 -57.00-150.00 26 15 \w 13.00 67.00 1.00 1.00 -- 40.98 -57.00-150.00 54 16 \w 87.00 131.00 1.00 1.00 -- 107.58 61.00-120.00 44 17 \w 82.00 115.00 1.00 1.00 -- 107.58-125.00-180.00 33 18 \w 152.00 178.00 1.00 1.00 -- 107.58 30.00 120.00 26 19 \w 43.00 69.00 1.00 1.00 -- 107.58 -77.00 -90.00 26 20 \w 80.00 133.00 1.00 1.00 -- 107.58 30.00 120.00 53 21 \w 87.00 140.00 1.00 1.00 -- 107.58 -77.00 -90.00 53 22 \w 72.00 102.00 1.00 1.00 -- 107.58 -94.00 30.00 30 23 \w 32.00 102.00 1.00 1.00 -- 107.58 -94.00-150.00 70 24 \w 79.00 122.00 1.00 1.00 -- 107.58 61.00 0.00 43 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.1349399000 _diffrn_orient_matrix_UB_12 0.0210215000 _diffrn_orient_matrix_UB_13 -0.1326997000 _diffrn_orient_matrix_UB_21 0.0348816000 _diffrn_orient_matrix_UB_22 0.1281155000 _diffrn_orient_matrix_UB_23 0.0327639000 _diffrn_orient_matrix_UB_31 0.2272973000 _diffrn_orient_matrix_UB_32 -0.0777568000 _diffrn_orient_matrix_UB_33 0.0344108000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_unetI/netI 0.0375 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.963 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 4814 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.963 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.163 _diffrn_reflns_theta_min 4.045 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 3.536 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.14245 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_density_diffrn 1.473 _exptl_crystal_description needle _exptl_crystal_F_000 320 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.510 _refine_diff_density_min -0.664 _refine_diff_density_rms 0.112 _refine_ls_extinction_coef 0.012(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 183 _refine_ls_number_reflns 2708 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.071 _refine_ls_R_factor_all 0.0586 _refine_ls_R_factor_gt 0.0574 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1187P)^2^+0.2066P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1588 _refine_ls_wR_factor_ref 0.1612 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2593 _reflns_number_total 2708 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5ob00022j2.cif _cod_data_source_block exp_5389 _cod_database_code 1573821 _shelx_shelxl_version_number 2018/3 _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. ; _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 Ternary CH refined with riding coordinates: C10(H10), C11(H11) 2.b Secondary CH2 refined with riding coordinates: C12(H12A,H12B), C14(H14A,H14B) 2.c Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C6(H6) 2.d Idealised Me refined as rotating group: C15(H15A,H15B,H15C) ; _shelx_res_file ; TITL exp_5389_a.res in P-1 exp_5389.res created by SHELXL-2018/3 at 19:59:36 on 21-May-2024 REM Old TITL exp_5389 in P-1 REM SHELXT solution in P-1: R1 0.131, Rweak 0.007, Alpha 0.044 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C15 O3 Cl2 CELL 1.54184 6.196 10.6217 11.347 82.619 74.785 73.76 ZERR 2 0.0003 0.0006 0.0006 0.004 0.005 0.005 LATT 1 SFAC C H O S UNIT 30 28 6 4 L.S. 10 PLAN 5 TEMP -120 CONF BOND LIST 4 fmap 2 MORE -1 ACTA BOND $H REM REM REM WGHT 0.118700 0.206600 EXTI 0.012481 FVAR 1.03278 S1 4 0.122303 0.119999 0.983162 11.00000 0.02415 0.01863 = 0.01715 0.00163 0.00028 -0.01379 S2 4 0.438502 0.282869 1.002324 11.00000 0.02772 0.02023 = 0.01659 0.00304 -0.00461 -0.01443 O1 3 0.085740 0.171920 0.742764 11.00000 0.02280 0.02938 = 0.02129 -0.00077 -0.00201 -0.01208 O2 3 0.116489 0.567121 0.652078 11.00000 0.05903 0.05324 = 0.04601 0.00193 -0.02908 0.00921 O3 3 0.426058 0.519444 0.881507 11.00000 0.04540 0.01737 = 0.02577 -0.00034 -0.01065 -0.01433 C1 1 0.393393 0.192578 0.573716 11.00000 0.02400 0.01323 = 0.01915 -0.00028 -0.00313 -0.00832 C2 1 0.267326 0.239860 0.485214 11.00000 0.02451 0.02127 = 0.02285 -0.00214 -0.00516 -0.00798 AFIX 43 H2 2 0.106405 0.280899 0.508734 11.00000 -1.20000 AFIX 0 C3 1 0.377918 0.226794 0.362080 11.00000 0.03691 0.02235 = 0.01988 -0.00035 -0.00685 -0.01141 AFIX 43 H3 2 0.293952 0.262473 0.301205 11.00000 -1.20000 AFIX 0 C4 1 0.609865 0.161960 0.328141 11.00000 0.03924 0.02662 = 0.01701 -0.00186 -0.00006 -0.01251 AFIX 43 H4 2 0.683559 0.150616 0.244105 11.00000 -1.20000 AFIX 0 C5 1 0.735313 0.113425 0.416384 11.00000 0.02790 0.02911 = 0.02393 -0.00370 0.00300 -0.00276 AFIX 43 H5 2 0.894264 0.068184 0.392792 11.00000 -1.20000 AFIX 0 C6 1 0.628552 0.130968 0.539221 11.00000 0.02529 0.02092 = 0.02150 -0.00087 -0.00279 -0.00368 AFIX 43 H6 2 0.715718 0.101023 0.599494 11.00000 -1.20000 AFIX 0 C7 1 0.271395 0.202955 0.706094 11.00000 0.01927 0.01413 = 0.01925 0.00043 -0.00319 -0.00402 C8 1 0.372354 0.247248 0.790719 11.00000 0.01927 0.01229 = 0.01747 0.00034 -0.00083 -0.00505 C9 1 0.311112 0.216865 0.913049 11.00000 0.01896 0.01159 = 0.01870 0.00053 -0.00135 -0.00648 C10 1 0.550821 0.327451 0.754930 11.00000 0.02154 0.01560 = 0.01609 0.00211 -0.00001 -0.00990 AFIX 13 H10 2 0.706762 0.267849 0.722695 11.00000 -1.20000 AFIX 0 C11 1 0.553444 0.386774 0.871828 11.00000 0.02714 0.01908 = 0.02059 0.00318 -0.00521 -0.01437 AFIX 13 H11 2 0.717644 0.380970 0.871176 11.00000 -1.20000 AFIX 0 C12 1 0.499744 0.440796 0.658802 11.00000 0.03557 0.01707 = 0.01836 0.00481 -0.00169 -0.01475 AFIX 23 H12A 2 0.615576 0.492716 0.643174 11.00000 -1.20000 H12B 2 0.506107 0.405749 0.580874 11.00000 -1.20000 AFIX 0 C13 1 0.262339 0.525204 0.708939 11.00000 0.04071 0.01795 = 0.02985 0.00479 -0.01091 -0.00616 C14 1 0.216634 0.549828 0.842901 11.00000 0.03742 0.01642 = 0.02710 -0.00024 -0.00294 -0.00193 AFIX 23 H14A 2 0.134640 0.643191 0.856014 11.00000 -1.20000 H14B 2 0.115690 0.495219 0.892694 11.00000 -1.20000 AFIX 0 C15 1 0.198343 0.070537 1.128722 11.00000 0.02842 0.02285 = 0.01814 0.00600 -0.00057 -0.01339 AFIX 137 H15A 2 0.366181 0.034252 1.114951 11.00000 -1.50000 H15B 2 0.119679 0.003599 1.171620 11.00000 -1.50000 H15C 2 0.150360 0.146968 1.178444 11.00000 -1.50000 AFIX 0 HKLF 4 REM exp_5389_a.res in P-1 REM wR2 = 0.1612, GooF = S = 1.071, Restrained GooF = 1.071 for all data REM R1 = 0.0574 for 2593 Fo > 4sig(Fo) and 0.0586 for all 2708 data REM 183 parameters refined using 0 restraints END WGHT 0.1187 0.2069 REM Highest difference peak 0.510, deepest hole -0.664, 1-sigma level 0.112 Q1 1 0.4558 0.1807 0.9791 11.00000 0.05 0.51 Q2 1 -0.0281 0.1468 1.0056 11.00000 0.05 0.49 Q3 1 0.2593 0.1203 0.9259 11.00000 0.05 0.49 Q4 1 0.2850 0.2928 1.0216 11.00000 0.05 0.48 Q5 1 0.2422 0.1312 0.9560 11.00000 0.05 0.47 ; _shelx_res_checksum 3988 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 4.147 _oxdiff_exptl_absorpt_empirical_full_min 0.476 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 0.12230(8) 0.12000(5) 0.98316(4) 0.0195(2) Uani 1 1 d . . . . . S2 S 0.43850(9) 0.28287(5) 1.00232(4) 0.0203(2) Uani 1 1 d . . . . . O1 O 0.0857(3) 0.17192(16) 0.74276(14) 0.0241(4) Uani 1 1 d . . . . . O2 O 0.1165(4) 0.5671(2) 0.6521(2) 0.0549(6) Uani 1 1 d . . . . . O3 O 0.4261(3) 0.51944(15) 0.88151(15) 0.0279(4) Uani 1 1 d . . . . . C1 C 0.3934(4) 0.1926(2) 0.57372(19) 0.0185(4) Uani 1 1 d . . . . . C2 C 0.2673(4) 0.2399(2) 0.4852(2) 0.0225(5) Uani 1 1 d . . . . . H2 H 0.106405 0.280899 0.508734 0.027 Uiso 1 1 calc R U . . . C3 C 0.3779(4) 0.2268(2) 0.3621(2) 0.0257(5) Uani 1 1 d . . . . . H3 H 0.293952 0.262473 0.301205 0.031 Uiso 1 1 calc R U . . . C4 C 0.6099(4) 0.1620(2) 0.3281(2) 0.0280(5) Uani 1 1 d . . . . . H4 H 0.683559 0.150616 0.244105 0.034 Uiso 1 1 calc R U . . . C5 C 0.7353(4) 0.1134(2) 0.4164(2) 0.0295(5) Uani 1 1 d . . . . . H5 H 0.894264 0.068184 0.392792 0.035 Uiso 1 1 calc R U . . . C6 C 0.6286(4) 0.1310(2) 0.5392(2) 0.0236(5) Uani 1 1 d . . . . . H6 H 0.715718 0.101023 0.599494 0.028 Uiso 1 1 calc R U . . . C7 C 0.2714(4) 0.2030(2) 0.70609(19) 0.0180(4) Uani 1 1 d . . . . . C8 C 0.3724(3) 0.24725(19) 0.79072(18) 0.0169(4) Uani 1 1 d . . . . . C9 C 0.3111(3) 0.21686(19) 0.91305(18) 0.0166(4) Uani 1 1 d . . . . . C10 C 0.5508(4) 0.3275(2) 0.75493(18) 0.0178(4) Uani 1 1 d . . . . . H10 H 0.706762 0.267849 0.722695 0.021 Uiso 1 1 calc R U . . . C11 C 0.5534(4) 0.3868(2) 0.8718(2) 0.0210(5) Uani 1 1 d . . . . . H11 H 0.717644 0.380970 0.871176 0.025 Uiso 1 1 calc R U . . . C12 C 0.4997(4) 0.4408(2) 0.6588(2) 0.0235(5) Uani 1 1 d . . . . . H12A H 0.615576 0.492716 0.643174 0.028 Uiso 1 1 calc R U . . . H12B H 0.506107 0.405749 0.580874 0.028 Uiso 1 1 calc R U . . . C13 C 0.2623(5) 0.5252(2) 0.7089(2) 0.0299(5) Uani 1 1 d . . . . . C14 C 0.2166(4) 0.5498(2) 0.8429(2) 0.0290(5) Uani 1 1 d . . . . . H14A H 0.134640 0.643191 0.856014 0.035 Uiso 1 1 calc R U . . . H14B H 0.115690 0.495219 0.892694 0.035 Uiso 1 1 calc R U . . . C15 C 0.1983(4) 0.0705(2) 1.12872(19) 0.0234(5) Uani 1 1 d . . . . . H15A H 0.366181 0.034252 1.114951 0.035 Uiso 1 1 calc R U . . . H15B H 0.119679 0.003599 1.171620 0.035 Uiso 1 1 calc R U . . . H15C H 0.150360 0.146968 1.178444 0.035 Uiso 1 1 calc R U . . . 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 0.0241(4) 0.0186(3) 0.0171(3) 0.0016(2) 0.0003(2) -0.0138(2) S2 0.0277(4) 0.0202(3) 0.0166(3) 0.0030(2) -0.0046(2) -0.0144(2) O1 0.0228(8) 0.0294(9) 0.0213(8) -0.0008(6) -0.0020(6) -0.0121(7) O2 0.0590(14) 0.0532(13) 0.0460(12) 0.0019(10) -0.0291(11) 0.0092(11) O3 0.0454(10) 0.0174(8) 0.0258(8) -0.0003(6) -0.0106(7) -0.0143(7) C1 0.0240(10) 0.0132(9) 0.0192(10) -0.0003(7) -0.0031(8) -0.0083(8) C2 0.0245(11) 0.0213(10) 0.0228(11) -0.0021(8) -0.0052(9) -0.0080(8) C3 0.0369(12) 0.0223(11) 0.0199(11) -0.0003(8) -0.0069(9) -0.0114(9) C4 0.0392(13) 0.0266(12) 0.0170(10) -0.0019(8) -0.0001(9) -0.0125(10) C5 0.0279(11) 0.0291(12) 0.0239(12) -0.0037(9) 0.0030(9) -0.0028(9) C6 0.0253(11) 0.0209(11) 0.0215(11) -0.0009(8) -0.0028(9) -0.0037(9) C7 0.0193(10) 0.0141(9) 0.0193(10) 0.0004(7) -0.0032(8) -0.0040(7) C8 0.0193(9) 0.0123(9) 0.0175(10) 0.0003(7) -0.0008(8) -0.0051(7) C9 0.0190(9) 0.0116(9) 0.0187(10) 0.0005(7) -0.0013(8) -0.0065(7) C10 0.0215(10) 0.0156(10) 0.0161(10) 0.0021(7) 0.0000(8) -0.0099(8) C11 0.0271(11) 0.0191(10) 0.0206(10) 0.0032(8) -0.0052(8) -0.0144(8) C12 0.0356(12) 0.0171(10) 0.0184(10) 0.0048(8) -0.0017(9) -0.0148(9) C13 0.0407(13) 0.0180(11) 0.0299(12) 0.0048(9) -0.0109(11) -0.0062(10) C14 0.0374(13) 0.0164(10) 0.0271(12) -0.0002(9) -0.0029(10) -0.0019(9) C15 0.0284(11) 0.0229(11) 0.0181(11) 0.0060(8) -0.0006(8) -0.0134(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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 C9 S1 C15 102.07(10) . . ? C9 S2 C11 92.00(10) . . ? C11 O3 C14 114.42(17) . . ? C2 C1 C6 120.1(2) . . ? C2 C1 C7 119.32(19) . . ? C6 C1 C7 120.52(19) . . ? C1 C2 H2 120.2 . . ? C1 C2 C3 119.7(2) . . ? C3 C2 H2 120.2 . . ? C2 C3 H3 119.9 . . ? C4 C3 C2 120.1(2) . . ? C4 C3 H3 119.9 . . ? C3 C4 H4 119.9 . . ? C3 C4 C5 120.2(2) . . ? C5 C4 H4 119.9 . . ? C4 C5 H5 120.0 . . ? C4 C5 C6 120.0(2) . . ? C6 C5 H5 120.0 . . ? C1 C6 H6 120.1 . . ? C5 C6 C1 119.8(2) . . ? C5 C6 H6 120.1 . . ? O1 C7 C1 119.04(19) . . ? O1 C7 C8 120.67(19) . . ? C8 C7 C1 120.29(18) . . ? C7 C8 C10 125.49(18) . . ? C9 C8 C7 120.68(19) . . ? C9 C8 C10 113.82(18) . . ? S1 C9 S2 119.61(12) . . ? C8 C9 S1 125.40(17) . . ? C8 C9 S2 114.99(16) . . ? C8 C10 H10 109.0 . . ? C8 C10 C11 107.58(16) . . ? C8 C10 C12 113.94(18) . . ? C11 C10 H10 109.0 . . ? C12 C10 H10 109.0 . . ? C12 C10 C11 108.16(17) . . ? S2 C11 H11 108.5 . . ? O3 C11 S2 111.28(15) . . ? O3 C11 C10 113.30(17) . . ? O3 C11 H11 108.5 . . ? C10 C11 S2 106.70(14) . . ? C10 C11 H11 108.5 . . ? C10 C12 H12A 110.3 . . ? C10 C12 H12B 110.3 . . ? H12A C12 H12B 108.5 . . ? C13 C12 C10 107.30(17) . . ? C13 C12 H12A 110.3 . . ? C13 C12 H12B 110.3 . . ? O2 C13 C12 124.7(2) . . ? O2 C13 C14 121.8(2) . . ? C12 C13 C14 113.4(2) . . ? O3 C14 C13 111.1(2) . . ? O3 C14 H14A 109.4 . . ? O3 C14 H14B 109.4 . . ? C13 C14 H14A 109.4 . . ? C13 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? S1 C15 H15A 109.5 . . ? S1 C15 H15B 109.5 . . ? S1 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 C9 1.742(2) . ? S1 C15 1.809(2) . ? S2 C9 1.747(2) . ? S2 C11 1.840(2) . ? O1 C7 1.237(3) . ? O2 C13 1.199(3) . ? O3 C11 1.412(3) . ? O3 C14 1.417(3) . ? C1 C2 1.391(3) . ? C1 C6 1.392(3) . ? C1 C7 1.497(3) . ? C2 H2 0.9500 . ? C2 C3 1.391(3) . ? C3 H3 0.9500 . ? C3 C4 1.383(4) . ? C4 H4 0.9500 . ? C4 C5 1.387(4) . ? C5 H5 0.9500 . ? C5 C6 1.389(3) . ? C6 H6 0.9500 . ? C7 C8 1.460(3) . ? C8 C9 1.361(3) . ? C8 C10 1.522(3) . ? C10 H10 1.0000 . ? C10 C11 1.545(3) . ? C10 C12 1.539(3) . ? C11 H11 1.0000 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C12 C13 1.498(3) . ? C13 C14 1.515(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C7 C8 C9 21.2(3) . . . . ? O1 C7 C8 C10 -159.4(2) . . . . ? O2 C13 C14 O3 -165.7(3) . . . . ? C1 C2 C3 C4 2.8(3) . . . . ? C1 C7 C8 C9 -157.88(19) . . . . ? C1 C7 C8 C10 21.5(3) . . . . ? C2 C1 C6 C5 -1.9(3) . . . . ? C2 C1 C7 O1 45.4(3) . . . . ? C2 C1 C7 C8 -135.5(2) . . . . ? C2 C3 C4 C5 -2.1(4) . . . . ? C3 C4 C5 C6 -0.6(4) . . . . ? C4 C5 C6 C1 2.6(4) . . . . ? C6 C1 C2 C3 -0.8(3) . . . . ? C6 C1 C7 O1 -131.7(2) . . . . ? C6 C1 C7 C8 47.4(3) . . . . ? C7 C1 C2 C3 -177.93(19) . . . . ? C7 C1 C6 C5 175.2(2) . . . . ? C7 C8 C9 S1 2.7(3) . . . . ? C7 C8 C9 S2 -177.50(14) . . . . ? C7 C8 C10 C11 163.27(18) . . . . ? C7 C8 C10 C12 43.4(3) . . . . ? C8 C10 C11 S2 22.7(2) . . . . ? C8 C10 C11 O3 -100.1(2) . . . . ? C8 C10 C12 C13 56.3(2) . . . . ? C9 S2 C11 O3 105.34(15) . . . . ? C9 S2 C11 C10 -18.71(15) . . . . ? C9 C8 C10 C11 -17.3(2) . . . . ? C9 C8 C10 C12 -137.20(19) . . . . ? C10 C8 C9 S1 -176.77(14) . . . . ? C10 C8 C9 S2 3.0(2) . . . . ? C10 C12 C13 O2 -134.7(3) . . . . ? C10 C12 C13 C14 43.0(3) . . . . ? C11 S2 C9 S1 -170.44(13) . . . . ? C11 S2 C9 C8 9.73(17) . . . . ? C11 O3 C14 C13 -61.6(2) . . . . ? C11 C10 C12 C13 -63.3(2) . . . . ? C12 C10 C11 S2 146.22(15) . . . . ? C12 C10 C11 O3 23.4(2) . . . . ? C12 C13 C14 O3 16.6(3) . . . . ? C14 O3 C11 S2 -81.0(2) . . . . ? C14 O3 C11 C10 39.3(2) . . . . ? C15 S1 C9 S2 -19.86(15) . . . . ? C15 S1 C9 C8 159.94(18) . . . . ?