#------------------------------------------------------------------------------ #$Date: 2021-09-17 03:23:46 +0300 (Fri, 17 Sep 2021) $ #$Revision: 269171 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158306.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_7158306 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 H19 N O S2' _chemical_formula_sum 'C20 H19 N O S2' _chemical_formula_weight 353.48 _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 2020-07-22 _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 101.4180(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.8601(3) _cell_length_b 11.9035(3) _cell_length_c 15.2689(4) _cell_measurement_reflns_used 9963 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 54.99 _cell_measurement_theta_min 3.98 _cell_volume 1756.64(8) _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 173.01 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.993 _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 0.0478 _diffrn_reflns_av_unetI/netI 0.0354 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 15677 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 54.961 _diffrn_reflns_theta_min 3.979 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.811 _exptl_absorpt_correction_T_max 0.7508 _exptl_absorpt_correction_T_min 0.5889 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1163 before and 0.0651 after correction. The Ratio of minimum to maximum transmission is 0.7283. The \l/2 correction factor is Not present.' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.337 _exptl_crystal_description block _exptl_crystal_F_000 744 _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.363 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.045 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 220 _refine_ls_number_reflns 3317 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.095 _refine_ls_R_factor_all 0.0356 _refine_ls_R_factor_gt 0.0343 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0405P)^2^+0.8314P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0925 _refine_ls_wR_factor_ref 0.0937 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3181 _reflns_number_total 3317 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01731d2.cif _cod_data_source_block mj20395_0m _cod_database_code 7158306 _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 0.899 _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, All O(H) groups 2.a Ternary CH refined with riding coordinates: C1(H1A) 2.b Secondary CH2 refined with riding coordinates: C13(H13A,H13B) 2.c Aromatic/amide H refined with riding coordinates: C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C15(H15), C16(H16), C18(H18), C19(H19) 2.d Idealised Me refined as rotating group: C11(H11A,H11B,H11C), C12(H12A,H12B,H12C) 2.e Idealised tetrahedral OH refined as rotating group: O1(H1) ; _shelx_res_file ; TITL mj20395_0m_a.res in P2(1)/c mj20395_0m.res created by SHELXL-2016/6 at 11:58:46 on 22-Jul-2020 REM Old TITL mj20395_0m in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.102, Rweak 0.004, Alpha 0.030, Orientation as input REM Formula found by SHELXT: C20 N O S2 CELL 1.34139 9.8601 11.9035 15.2689 90 101.418 90 ZERR 4 0.0003 0.0003 0.0004 0 0.001 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O S DISP C 0.0148 0.007 57.7477 DISP H -0 0 0.6481 DISP N 0.0253 0.0136 110.5121 DISP O 0.0412 0.025 193.9543 DISP S 0.2924 0.4247 3241.7632 UNIT 80 76 4 4 8 L.S. 4 PLAN 20 SIZE 0.06 0.08 0.08 TEMP -100.14 BOND $H list 4 fmap 2 acta OMIT 2 1 2 OMIT 2 2 0 REM REM REM WGHT 0.040500 0.831400 FVAR 0.93550 S1 5 0.342912 0.621769 0.706058 11.00000 0.02376 0.03791 = 0.02103 0.00146 0.00326 -0.00535 S2 5 0.498758 0.669737 0.645651 11.00000 0.02079 0.03232 = 0.03053 0.00463 0.00566 0.00063 O1 4 0.108105 0.518663 0.743773 11.00000 0.02707 0.05431 = 0.03027 0.01410 0.00917 0.00139 AFIX 147 H1 2 0.034381 0.498287 0.758772 11.00000 -1.50000 AFIX 0 N1 3 0.898486 1.009110 0.353273 11.00000 0.04513 0.05357 = 0.05089 0.00025 0.02561 -0.00234 C1 1 0.081008 0.545202 0.650883 11.00000 0.02279 0.03002 = 0.02617 0.00199 0.00298 -0.00248 AFIX 13 H1A 2 0.017260 0.486564 0.618833 11.00000 -1.20000 AFIX 0 C2 1 0.220220 0.534658 0.620627 11.00000 0.02337 0.02668 = 0.02390 0.00102 0.00312 -0.00003 C3 1 0.210581 0.582838 0.527734 11.00000 0.02578 0.02951 = 0.02304 0.00012 0.00142 -0.00596 C4 1 0.288699 0.540698 0.468803 11.00000 0.02900 0.03630 = 0.02971 -0.00225 0.00436 -0.00316 AFIX 43 H4 2 0.349179 0.479073 0.486408 11.00000 -1.20000 AFIX 0 C5 1 0.279583 0.587572 0.384204 11.00000 0.03447 0.04787 = 0.02818 -0.00572 0.00783 -0.00910 AFIX 43 H5 2 0.332145 0.556588 0.344225 11.00000 -1.20000 AFIX 0 C6 1 0.194986 0.678384 0.358233 11.00000 0.03969 0.04605 = 0.02459 0.00552 0.00180 -0.01489 AFIX 43 H6 2 0.189900 0.710860 0.300840 11.00000 -1.20000 AFIX 0 C7 1 0.117167 0.722164 0.416506 11.00000 0.03754 0.03123 = 0.02976 0.00446 -0.00293 -0.00391 AFIX 43 H7 2 0.059674 0.785565 0.398977 11.00000 -1.20000 AFIX 0 C8 1 0.122146 0.674051 0.501165 11.00000 0.02900 0.02819 = 0.02639 -0.00106 -0.00013 -0.00550 C9 1 0.032914 0.715549 0.559716 11.00000 0.03118 0.02730 = 0.03207 -0.00082 -0.00129 0.00487 AFIX 43 H9 2 -0.011874 0.785966 0.546661 11.00000 -1.20000 AFIX 0 C10 1 0.011980 0.658328 0.630760 11.00000 0.02236 0.03162 = 0.02850 -0.00371 -0.00001 0.00114 C11 1 -0.090134 0.695083 0.685815 11.00000 0.03133 0.04596 = 0.03818 -0.00577 0.00627 0.00710 AFIX 137 H11A 2 -0.163058 0.638340 0.682135 11.00000 -1.50000 H11B 2 -0.131295 0.766918 0.663105 11.00000 -1.50000 H11C 2 -0.042810 0.704022 0.748199 11.00000 -1.50000 AFIX 0 C12 1 0.269873 0.413486 0.629006 11.00000 0.03561 0.02814 = 0.03521 0.00326 0.00802 0.00486 AFIX 137 H12A 2 0.366784 0.410222 0.622687 11.00000 -1.50000 H12B 2 0.213067 0.368118 0.582051 11.00000 -1.50000 H12C 2 0.261772 0.384017 0.687681 11.00000 -1.50000 AFIX 0 C13 1 0.443007 0.809730 0.602427 11.00000 0.02664 0.03221 = 0.04501 0.00768 0.01117 0.00273 AFIX 23 H13A 2 0.349638 0.805224 0.564058 11.00000 -1.20000 H13B 2 0.438684 0.861353 0.652636 11.00000 -1.20000 AFIX 0 C14 1 0.544722 0.853214 0.549204 11.00000 0.02309 0.02550 = 0.03273 0.00575 0.00434 0.00228 C15 1 0.649580 0.926078 0.587327 11.00000 0.03063 0.03150 = 0.02593 -0.00176 0.00396 -0.00048 AFIX 43 H15 2 0.657659 0.948214 0.647918 11.00000 -1.20000 AFIX 0 C16 1 0.742636 0.966949 0.538132 11.00000 0.02611 0.03074 = 0.03257 -0.00334 0.00415 -0.00515 AFIX 43 H16 2 0.814262 1.016864 0.564646 11.00000 -1.20000 AFIX 0 C17 1 0.730148 0.934120 0.449359 11.00000 0.02289 0.02735 = 0.03089 0.00396 0.00721 0.00427 C18 1 0.625997 0.860606 0.410409 11.00000 0.03403 0.03724 = 0.02687 -0.00382 0.00303 -0.00007 AFIX 43 H18 2 0.617983 0.838246 0.349875 11.00000 -1.20000 AFIX 0 C19 1 0.534360 0.820417 0.460503 11.00000 0.02839 0.03671 = 0.03558 -0.00432 0.00076 -0.00875 AFIX 43 H19 2 0.463386 0.769806 0.434226 11.00000 -1.20000 AFIX 0 C20 1 0.824923 0.976339 0.396328 11.00000 0.03270 0.03449 = 0.03841 0.00071 0.01192 0.00528 HKLF 4 REM mj20395_0m_a.res in P2(1)/c REM R1 = 0.0343 for 3181 Fo > 4sig(Fo) and 0.0356 for all 3317 data REM 220 parameters refined using 0 restraints END WGHT 0.0401 0.8395 REM Highest difference peak 0.363, deepest hole -0.393, 1-sigma level 0.045 Q1 1 0.3011 0.6944 0.7040 11.00000 0.05 0.36 Q2 1 0.1883 0.6379 0.5259 11.00000 0.05 0.24 Q3 1 0.4568 0.7443 0.6233 11.00000 0.05 0.24 Q4 1 0.7439 0.9408 0.4968 11.00000 0.05 0.24 Q5 1 0.4196 0.5565 0.7326 11.00000 0.05 0.24 Q6 1 0.2161 0.5574 0.5698 11.00000 0.05 0.23 Q7 1 0.6941 0.8945 0.4380 11.00000 0.05 0.23 Q8 1 0.1386 0.7208 0.4724 11.00000 0.05 0.21 Q9 1 0.5131 0.5657 0.6455 11.00000 0.05 0.20 Q10 1 0.1419 0.4495 0.7355 11.00000 0.05 0.20 Q11 1 0.5739 0.9040 0.5627 11.00000 0.05 0.19 Q12 1 0.4744 0.6736 0.7061 11.00000 0.05 0.19 Q13 1 0.2716 0.5702 0.6675 11.00000 0.05 0.19 Q14 1 0.5547 0.7330 0.6853 11.00000 0.05 0.19 Q15 1 0.5418 0.8355 0.5121 11.00000 0.05 0.18 Q16 1 0.1773 0.7483 0.3903 11.00000 0.05 0.18 Q17 1 0.0442 0.6138 0.6413 11.00000 0.05 0.18 Q18 1 0.5297 0.8587 0.5003 11.00000 0.05 0.17 Q19 1 0.2286 0.4639 0.6107 11.00000 0.05 0.17 Q20 1 0.2648 0.6576 0.3814 11.00000 0.05 0.17 ; _shelx_res_checksum 10824 _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 0.34291(4) 0.62177(4) 0.70606(2) 0.02772(13) Uani 1 1 d . . . . . S2 S 0.49876(4) 0.66974(3) 0.64565(3) 0.02780(13) Uani 1 1 d . . . . . O1 O 0.10810(12) 0.51866(12) 0.74377(8) 0.0367(3) Uani 1 1 d . . . . . H1 H 0.034381 0.498287 0.758772 0.055 Uiso 1 1 calc GR . . . . N1 N 0.89849(18) 1.00911(16) 0.35327(12) 0.0476(4) Uani 1 1 d . . . . . C1 C 0.08101(16) 0.54520(14) 0.65088(10) 0.0266(3) Uani 1 1 d . . . . . H1A H 0.017260 0.486564 0.618833 0.032 Uiso 1 1 calc R . . . . C2 C 0.22022(16) 0.53466(13) 0.62063(10) 0.0249(3) Uani 1 1 d . . . . . C3 C 0.21058(16) 0.58284(14) 0.52773(10) 0.0266(3) Uani 1 1 d . . . . . C4 C 0.28870(17) 0.54070(15) 0.46880(11) 0.0319(4) Uani 1 1 d . . . . . H4 H 0.349179 0.479073 0.486408 0.038 Uiso 1 1 calc R . . . . C5 C 0.27958(19) 0.58757(17) 0.38420(11) 0.0366(4) Uani 1 1 d . . . . . H5 H 0.332145 0.556588 0.344225 0.044 Uiso 1 1 calc R . . . . C6 C 0.19499(19) 0.67838(16) 0.35823(11) 0.0374(4) Uani 1 1 d . . . . . H6 H 0.189900 0.710860 0.300840 0.045 Uiso 1 1 calc R . . . . C7 C 0.11717(19) 0.72216(15) 0.41651(11) 0.0342(4) Uani 1 1 d . . . . . H7 H 0.059674 0.785565 0.398977 0.041 Uiso 1 1 calc R . . . . C8 C 0.12215(17) 0.67405(13) 0.50116(11) 0.0286(4) Uani 1 1 d . . . . . C9 C 0.03291(17) 0.71555(14) 0.55972(11) 0.0312(4) Uani 1 1 d . . . . . H9 H -0.011874 0.785966 0.546661 0.037 Uiso 1 1 calc R . . . . C10 C 0.01198(16) 0.65833(14) 0.63076(11) 0.0282(3) Uani 1 1 d . . . . . C11 C -0.09013(19) 0.69508(17) 0.68582(12) 0.0386(4) Uani 1 1 d . . . . . H11A H -0.163058 0.638340 0.682135 0.058 Uiso 1 1 calc GR . . . . H11B H -0.131295 0.766918 0.663105 0.058 Uiso 1 1 calc GR . . . . H11C H -0.042810 0.704022 0.748199 0.058 Uiso 1 1 calc GR . . . . C12 C 0.26987(18) 0.41349(14) 0.62901(12) 0.0328(4) Uani 1 1 d . . . . . H12A H 0.366784 0.410222 0.622687 0.049 Uiso 1 1 calc GR . . . . H12B H 0.213067 0.368118 0.582051 0.049 Uiso 1 1 calc GR . . . . H12C H 0.261772 0.384017 0.687681 0.049 Uiso 1 1 calc GR . . . . C13 C 0.44301(18) 0.80973(15) 0.60243(13) 0.0341(4) Uani 1 1 d . . . . . H13A H 0.349638 0.805224 0.564058 0.041 Uiso 1 1 calc R . . . . H13B H 0.438684 0.861353 0.652636 0.041 Uiso 1 1 calc R . . . . C14 C 0.54472(16) 0.85321(14) 0.54920(11) 0.0273(3) Uani 1 1 d . . . . . C15 C 0.64958(17) 0.92608(14) 0.58733(11) 0.0296(4) Uani 1 1 d . . . . . H15 H 0.657659 0.948214 0.647918 0.035 Uiso 1 1 calc R . . . . C16 C 0.74264(17) 0.96695(14) 0.53813(11) 0.0300(4) Uani 1 1 d . . . . . H16 H 0.814262 1.016864 0.564646 0.036 Uiso 1 1 calc R . . . . C17 C 0.73015(16) 0.93412(13) 0.44936(11) 0.0268(3) Uani 1 1 d . . . . . C18 C 0.62600(18) 0.86061(15) 0.41041(11) 0.0331(4) Uani 1 1 d . . . . . H18 H 0.617983 0.838246 0.349875 0.040 Uiso 1 1 calc R . . . . C19 C 0.53436(18) 0.82042(15) 0.46050(12) 0.0343(4) Uani 1 1 d . . . . . H19 H 0.463386 0.769806 0.434226 0.041 Uiso 1 1 calc R . . . . C20 C 0.82492(18) 0.97634(15) 0.39633(12) 0.0345(4) 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 S1 0.0238(2) 0.0379(3) 0.0210(2) 0.00146(15) 0.00326(15) -0.00535(15) S2 0.0208(2) 0.0323(2) 0.0305(2) 0.00463(16) 0.00566(15) 0.00063(15) O1 0.0271(6) 0.0543(8) 0.0303(6) 0.0141(5) 0.0092(5) 0.0014(6) N1 0.0451(10) 0.0536(10) 0.0509(10) 0.0002(8) 0.0256(8) -0.0023(8) C1 0.0228(8) 0.0300(8) 0.0262(8) 0.0020(6) 0.0030(6) -0.0025(6) C2 0.0234(8) 0.0267(8) 0.0239(7) 0.0010(6) 0.0031(6) 0.0000(6) C3 0.0258(8) 0.0295(8) 0.0230(7) 0.0001(6) 0.0014(6) -0.0060(6) C4 0.0290(8) 0.0363(9) 0.0297(8) -0.0022(7) 0.0044(7) -0.0032(7) C5 0.0345(9) 0.0479(11) 0.0282(8) -0.0057(8) 0.0078(7) -0.0091(8) C6 0.0397(10) 0.0461(11) 0.0246(8) 0.0055(7) 0.0018(7) -0.0149(8) C7 0.0375(9) 0.0312(9) 0.0298(8) 0.0045(7) -0.0029(7) -0.0039(7) C8 0.0290(8) 0.0282(8) 0.0264(8) -0.0011(6) -0.0001(6) -0.0055(7) C9 0.0312(9) 0.0273(8) 0.0321(8) -0.0008(7) -0.0013(7) 0.0049(7) C10 0.0224(8) 0.0316(9) 0.0285(8) -0.0037(6) 0.0000(6) 0.0011(6) C11 0.0313(9) 0.0460(11) 0.0382(9) -0.0058(8) 0.0063(7) 0.0071(8) C12 0.0356(9) 0.0281(9) 0.0352(9) 0.0033(7) 0.0080(7) 0.0049(7) C13 0.0266(9) 0.0322(9) 0.0450(10) 0.0077(8) 0.0112(7) 0.0027(7) C14 0.0231(8) 0.0255(8) 0.0327(8) 0.0057(6) 0.0043(6) 0.0023(6) C15 0.0306(8) 0.0315(9) 0.0259(8) -0.0018(7) 0.0040(6) -0.0005(7) C16 0.0261(8) 0.0307(9) 0.0326(8) -0.0033(7) 0.0041(7) -0.0052(7) C17 0.0229(7) 0.0274(8) 0.0309(8) 0.0040(6) 0.0072(6) 0.0043(6) C18 0.0340(9) 0.0372(9) 0.0269(8) -0.0038(7) 0.0030(7) -0.0001(7) C19 0.0284(9) 0.0367(9) 0.0356(9) -0.0043(7) 0.0008(7) -0.0088(7) C20 0.0327(9) 0.0345(9) 0.0384(9) 0.0007(7) 0.0119(8) 0.0053(7) 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' N N 0.0253 0.0136 '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 C2 S1 S2 106.17(5) . . ? C13 S2 S1 102.68(6) . . ? C1 O1 H1 109.5 . . ? O1 C1 H1A 107.9 . . ? O1 C1 C2 106.15(12) . . ? O1 C1 C10 112.80(13) . . ? C2 C1 H1A 107.9 . . ? C10 C1 H1A 107.9 . . ? C10 C1 C2 113.84(13) . . ? C1 C2 S1 103.53(10) . . ? C3 C2 S1 110.44(11) . . ? C3 C2 C1 110.86(13) . . ? C3 C2 C12 113.41(13) . . ? C12 C2 S1 108.00(11) . . ? C12 C2 C1 110.11(13) . . ? C4 C3 C2 121.98(15) . . ? C4 C3 C8 119.04(15) . . ? C8 C3 C2 118.97(14) . . ? C3 C4 H4 119.5 . . ? C3 C4 C5 120.91(17) . . ? C5 C4 H4 119.5 . . ? C4 C5 H5 119.8 . . ? C6 C5 C4 120.41(17) . . ? C6 C5 H5 119.8 . . ? C5 C6 H6 120.3 . . ? C5 C6 C7 119.45(16) . . ? C7 C6 H6 120.3 . . ? C6 C7 H7 119.5 . . ? C6 C7 C8 120.93(17) . . ? C8 C7 H7 119.5 . . ? C3 C8 C7 119.23(16) . . ? C3 C8 C9 120.07(15) . . ? C7 C8 C9 120.66(16) . . ? C8 C9 H9 118.8 . . ? C10 C9 C8 122.39(16) . . ? C10 C9 H9 118.8 . . ? C9 C10 C1 119.01(15) . . ? C9 C10 C11 122.51(16) . . ? C11 C10 C1 118.11(15) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C2 C12 H12A 109.5 . . ? C2 C12 H12B 109.5 . . ? C2 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? S2 C13 H13A 109.9 . . ? S2 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? C14 C13 S2 108.83(11) . . ? C14 C13 H13A 109.9 . . ? C14 C13 H13B 109.9 . . ? C15 C14 C13 120.71(15) . . ? C15 C14 C19 119.24(15) . . ? C19 C14 C13 120.05(15) . . ? C14 C15 H15 119.6 . . ? C16 C15 C14 120.76(15) . . ? C16 C15 H15 119.6 . . ? C15 C16 H16 120.4 . . ? C15 C16 C17 119.29(15) . . ? C17 C16 H16 120.4 . . ? C16 C17 C20 120.42(15) . . ? C18 C17 C16 120.57(15) . . ? C18 C17 C20 119.01(15) . . ? C17 C18 H18 120.3 . . ? C19 C18 C17 119.37(15) . . ? C19 C18 H18 120.3 . . ? C14 C19 H19 119.6 . . ? C18 C19 C14 120.76(16) . . ? C18 C19 H19 119.6 . . ? N1 C20 C17 178.9(2) . . ? 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 2.0246(5) . ? S1 C2 1.9014(16) . ? S2 C13 1.8360(17) . ? O1 H1 0.8400 . ? O1 C1 1.4258(19) . ? N1 C20 1.140(2) . ? C1 H1A 1.0000 . ? C1 C2 1.538(2) . ? C1 C10 1.513(2) . ? C2 C3 1.515(2) . ? C2 C12 1.520(2) . ? C3 C4 1.389(2) . ? C3 C8 1.401(2) . ? C4 H4 0.9500 . ? C4 C5 1.394(2) . ? C5 H5 0.9500 . ? C5 C6 1.375(3) . ? C6 H6 0.9500 . ? C6 C7 1.386(3) . ? C7 H7 0.9500 . ? C7 C8 1.406(2) . ? C8 C9 1.459(2) . ? C9 H9 0.9500 . ? C9 C10 1.331(2) . ? C10 C11 1.499(2) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C13 C14 1.502(2) . ? C14 C15 1.386(2) . ? C14 C19 1.394(2) . ? C15 H15 0.9500 . ? C15 C16 1.384(2) . ? C16 H16 0.9500 . ? C16 C17 1.393(2) . ? C17 C18 1.390(2) . ? C17 C20 1.443(2) . ? C18 H18 0.9500 . ? C18 C19 1.380(3) . ? C19 H19 0.9500 . ?