#------------------------------------------------------------------------------ #$Date: 2019-01-19 01:18:16 +0200 (Sat, 19 Jan 2019) $ #$Revision: 213214 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/04/1550493.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_1550493 loop_ _publ_author_name 'Lei, Aiwen' 'Li, Dan-Dan' 'Li, Shuaibing' 'Peng, Chong' 'Lu, Lijun' 'Wang , Shengchun' 'Wang, Pan' 'Chen, Yi-Hung' 'Cong, Hengjiang' _publ_section_title ; Electrochemical Oxidative C-H/S-H Cross-Coupling between Enamines and Thiophenols with H2 Evolution ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C8SC05143G _journal_year 2019 _chemical_formula_sum 'C20 H20 Cl N O2 S' _chemical_formula_weight 373.88 _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' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2016/4 _audit_update_record ; 2018-09-15 deposited with the CCDC. 2019-01-07 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.176(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.5425(5) _cell_length_b 20.2515(9) _cell_length_c 8.2218(4) _cell_measurement_reflns_used 8070 _cell_measurement_temperature 253(2) _cell_measurement_theta_max 28.67 _cell_measurement_theta_min 2.68 _cell_volume 1920.48(15) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX3' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2016/4 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 253(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker Kappa APEX-Duo CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_unetI/netI 0.0184 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 22022 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.717 _diffrn_reflns_theta_min 1.766 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.320 _exptl_absorpt_correction_T_max 0.7458 _exptl_absorpt_correction_T_min 0.7063 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2012/1 (Bruker,2012)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_meas ? _exptl_crystal_description stick _exptl_crystal_F_000 784 _exptl_crystal_size_max 0.160 _exptl_crystal_size_mid 0.080 _exptl_crystal_size_min 0.060 _refine_diff_density_max 0.399 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 295 _refine_ls_number_reflns 4969 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.030 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0408 _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^)+(0.0585P)^2^+0.5039P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1063 _refine_ls_wR_factor_ref 0.1159 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3986 _reflns_number_total 4969 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c8sc05143g2.cif _cod_data_source_block x_a _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas ; _cod_database_code 1550493 _shelx_shelxl_version_number 2016/4 _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_min 0.951 _shelx_estimated_absorpt_t_max 0.981 _shelx_res_file ; TITL x_a.res in P2(1)/c x_a.res created by SHELXL-2016/4 at 18:06:30 on 03-Aug-2018 REM Old TITL x in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.152, Rweak 0.009, Alpha 0.021, Orientation as input REM Formula found by SHELXT: C19 N O3 S Cl CELL 0.71073 11.5425 20.2515 8.2218 90.000 92.176 90.000 ZERR 4.000 0.0005 0.0009 0.0004 0.000 0.002 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H N O S CL UNIT 80 80 4 8 4 4 TEMP -20 ACTA SIZE 0.06 0.08 0.16 L.S. 10 BOND $H CONF HTAB LIST 6 FMAP 2 PLAN 20 WGHT 0.058500 0.503900 FVAR 0.60987 S1 5 0.804728 0.402066 0.283977 11.00000 0.04055 0.04492 = 0.03637 -0.00600 0.00289 0.00747 H1 2 0.765471 0.336830 0.741610 11.00000 0.05970 CL1 6 0.342716 0.256225 0.071632 11.00000 0.06896 0.06981 = 0.09501 -0.01822 -0.00460 -0.02207 N1 3 0.790110 0.491033 0.714817 11.00000 0.06161 0.05083 = 0.03661 -0.00728 -0.00963 0.01886 O1 4 0.678401 0.561156 0.489436 11.00000 0.07454 0.04636 = 0.04909 -0.00783 -0.00864 0.02341 C1 1 0.888125 0.391429 0.638096 11.00000 0.03719 0.03492 = 0.03619 -0.00044 -0.00459 0.00188 O2 4 0.678229 0.523827 0.233453 11.00000 0.05233 0.04938 = 0.03803 0.00769 -0.00083 0.01232 H2 2 0.890208 0.249789 0.812713 11.00000 0.08193 C2 1 0.844939 0.337351 0.718305 11.00000 0.05401 0.04395 = 0.06305 0.00832 0.00486 -0.00151 C3 1 0.918415 0.285622 0.764296 11.00000 0.09079 0.03723 = 0.07234 0.01117 -0.00732 -0.00073 H3 2 1.086150 0.251396 0.766434 11.00000 0.08138 C4 1 1.033660 0.288224 0.729322 11.00000 0.07385 0.04547 = 0.08305 -0.00446 -0.02202 0.02131 H4 2 1.155344 0.343917 0.621584 11.00000 0.10512 C5 1 1.077005 0.341289 0.649271 11.00000 0.04393 0.06188 = 0.09308 -0.00412 -0.00654 0.01524 H5 2 1.032207 0.430471 0.547296 11.00000 0.07412 C7 1 0.812596 0.449266 0.594492 11.00000 0.03157 0.03430 = 0.03675 -0.00056 0.00009 -0.00042 H7 2 0.392524 0.357276 0.298904 11.00000 0.05354 C6 1 1.004311 0.393106 0.602212 11.00000 0.03975 0.04787 = 0.06626 0.00475 0.00024 0.00340 H6 2 0.561354 0.411567 0.376192 11.00000 0.04942 C8 1 0.771514 0.459688 0.435555 11.00000 0.03781 0.03317 = 0.03468 -0.00169 0.00070 0.00370 H8 2 0.579787 0.246452 -0.010228 11.00000 0.06167 C9 1 0.706598 0.518999 0.392260 11.00000 0.03885 0.03721 = 0.03816 0.00174 -0.00105 0.00168 H9 2 0.746077 0.304198 0.073727 11.00000 0.06350 C10 1 0.608757 0.580457 0.181359 11.00000 0.06090 0.05700 = 0.05361 0.01797 -0.00329 0.01578 H10 2 0.748170 0.524836 0.686229 11.00000 0.06132 C11 1 0.483445 0.566561 0.198896 11.00000 0.05871 0.11663 = 0.09571 0.02824 -0.00413 0.02487 AFIX 137 H11A 2 0.438589 0.603340 0.158204 11.00000 -1.50000 H11B 2 0.468408 0.559746 0.311702 11.00000 -1.50000 H11C 2 0.462377 0.527619 0.138110 11.00000 -1.50000 AFIX 0 H11 2 0.887715 0.453659 0.896763 11.00000 0.06811 C12 1 0.828096 0.486705 0.885223 11.00000 0.06219 0.06152 = 0.03508 -0.00575 -0.00834 0.00862 H12 2 0.759498 0.474097 0.949889 11.00000 0.07115 C13 1 0.870695 0.550177 0.952953 11.00000 0.05130 0.07554 = 0.04758 -0.01375 -0.00312 0.00146 H13 2 0.624493 0.585587 0.065967 11.00000 0.07768 C14 1 0.891577 0.603726 0.875460 11.00000 0.10153 0.07876 = 0.08191 -0.00941 0.00093 -0.02103 H14 2 0.639923 0.619174 0.235125 11.00000 0.08355 C15 1 0.671209 0.362453 0.234379 11.00000 0.04655 0.03312 = 0.03017 -0.00023 0.00011 0.00607 H15 2 0.882327 0.550555 1.078628 11.00000 0.08677 C16 1 0.565946 0.378123 0.301326 11.00000 0.05110 0.03360 = 0.03788 -0.00500 0.00695 0.00206 H16 2 0.921843 0.640489 0.937417 11.00000 0.11679 C17 1 0.465135 0.345270 0.251768 11.00000 0.04849 0.03767 = 0.04978 0.00130 0.00652 0.00123 H17 2 0.881437 0.604097 0.760372 11.00000 0.09518 C18 1 0.470116 0.296474 0.135518 11.00000 0.05445 0.03795 = 0.05212 0.00014 -0.00429 -0.00426 C19 1 0.573546 0.279689 0.067741 11.00000 0.06744 0.04726 = 0.05296 -0.01894 -0.00329 0.00316 C20 1 0.673603 0.312832 0.117158 11.00000 0.05279 0.04873 = 0.04633 -0.01379 0.00313 0.01100 HKLF 4 REM x_a.res in P2(1)/c REM R1 = 0.0408 for 3986 Fo > 4sig(Fo) and 0.0543 for all 4969 data REM 295 parameters refined using 0 restraints END WGHT 0.0567 0.5250 REM Instructions for potential hydrogen bonds EQIV $1 -x+1, -y+1, -z+ HTAB C17 O1_$1 HTAB N1 O1 REM Highest difference peak 0.399, deepest hole -0.196, 1-sigma level 0.041 Q1 1 0.9156 0.5552 0.8657 11.00000 0.05 0.40 Q2 1 0.4055 0.2340 0.1072 11.00000 0.05 0.29 Q3 1 0.8517 0.4185 0.6133 11.00000 0.05 0.29 Q4 1 0.7937 0.4421 0.3666 11.00000 0.05 0.28 Q5 1 0.7490 0.4867 0.4190 11.00000 0.05 0.28 Q6 1 0.7273 0.3799 0.2643 11.00000 0.05 0.28 Q7 1 0.5209 0.3504 0.3033 11.00000 0.05 0.24 Q8 1 0.9444 0.3989 0.6534 11.00000 0.05 0.23 Q9 1 0.8129 0.4591 0.5003 11.00000 0.05 0.23 Q10 1 0.6179 0.3059 0.0779 11.00000 0.05 0.23 Q11 1 0.3213 0.2644 0.1629 11.00000 0.05 0.22 Q12 1 0.6261 0.3628 0.2740 11.00000 0.05 0.22 Q13 1 0.8367 0.4877 0.6515 11.00000 0.05 0.21 Q14 1 0.6699 0.3467 0.1547 11.00000 0.05 0.21 Q15 1 0.7698 0.4464 0.5143 11.00000 0.05 0.21 Q16 1 0.4183 0.2773 0.0932 11.00000 0.05 0.21 Q17 1 0.4757 0.3124 0.2263 11.00000 0.05 0.20 Q18 1 1.0412 0.3736 0.6665 11.00000 0.05 0.20 Q19 1 0.9329 0.3838 0.5777 11.00000 0.05 0.20 Q20 1 0.5377 0.2832 0.1388 11.00000 0.05 0.19 ; _shelx_res_checksum 35073 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 S1 S 0.80473(3) 0.40207(2) 0.28398(4) 0.04058(11) Uani 1 1 d . . H1 H 0.7655(19) 0.3368(10) 0.742(2) 0.060(6) Uiso 1 1 d . . CL1 Cl 0.34272(5) 0.25622(3) 0.07163(8) 0.07812(18) Uani 1 1 d . . N1 N 0.79011(13) 0.49103(7) 0.71482(16) 0.0500(3) Uani 1 1 d . . O1 O 0.67840(12) 0.56116(6) 0.48944(15) 0.0569(3) Uani 1 1 d . . C1 C 0.88812(12) 0.39143(7) 0.63810(17) 0.0363(3) Uani 1 1 d . . O2 O 0.67823(10) 0.52383(6) 0.23345(13) 0.0466(3) Uani 1 1 d . . H2 H 0.890(2) 0.2498(13) 0.813(3) 0.082(7) Uiso 1 1 d . . C2 C 0.84494(17) 0.33735(9) 0.7183(2) 0.0536(4) Uani 1 1 d . . C3 C 0.9184(2) 0.28562(10) 0.7643(3) 0.0671(5) Uani 1 1 d . . H3 H 1.086(2) 0.2514(12) 0.766(3) 0.081(7) Uiso 1 1 d . . C4 C 1.0337(2) 0.28822(10) 0.7293(3) 0.0681(6) Uani 1 1 d . . H4 H 1.155(3) 0.3439(14) 0.622(4) 0.105(9) Uiso 1 1 d . . C5 C 1.07701(17) 0.34129(11) 0.6493(3) 0.0665(5) Uani 1 1 d . . H5 H 1.032(2) 0.4305(12) 0.547(3) 0.074(7) Uiso 1 1 d . . C7 C 0.81260(11) 0.44927(7) 0.59449(16) 0.0342(3) Uani 1 1 d . . H7 H 0.3925(17) 0.3573(9) 0.299(2) 0.054(5) Uiso 1 1 d . . C6 C 1.00431(14) 0.39311(9) 0.6022(2) 0.0513(4) Uani 1 1 d . . H6 H 0.5614(16) 0.4116(9) 0.376(2) 0.049(5) Uiso 1 1 d . . C8 C 0.77151(12) 0.45969(7) 0.43556(16) 0.0352(3) Uani 1 1 d . . H8 H 0.5798(18) 0.2465(10) -0.010(3) 0.062(6) Uiso 1 1 d . . C9 C 0.70660(12) 0.51900(7) 0.39226(17) 0.0381(3) Uani 1 1 d . . H9 H 0.7461(19) 0.3042(10) 0.074(2) 0.063(6) Uiso 1 1 d . . C10 C 0.60876(17) 0.58046(10) 0.1814(3) 0.0573(5) Uani 1 1 d . . H10 H 0.7482(18) 0.5248(11) 0.686(2) 0.061(6) Uiso 1 1 d . . C11 C 0.4834(2) 0.56656(15) 0.1989(3) 0.0905(8) Uani 1 1 d . . H11A H 0.438589 0.603340 0.158204 0.136 Uiso 1 1 calc R U H11B H 0.468408 0.559746 0.311702 0.136 Uiso 1 1 calc R U H11C H 0.462377 0.527619 0.138110 0.136 Uiso 1 1 calc R U H11 H 0.8877(19) 0.4537(11) 0.897(3) 0.068(6) Uiso 1 1 d . . C12 C 0.82810(18) 0.48670(10) 0.8852(2) 0.0532(4) Uani 1 1 d . . H12 H 0.759(2) 0.4741(11) 0.950(3) 0.071(6) Uiso 1 1 d . . C13 C 0.87070(16) 0.55018(11) 0.9530(2) 0.0583(5) Uani 1 1 d . . H13 H 0.624(2) 0.5856(12) 0.066(3) 0.078(7) Uiso 1 1 d . . C14 C 0.8916(3) 0.60373(15) 0.8755(4) 0.0875(8) Uani 1 1 d . . H14 H 0.640(2) 0.6192(13) 0.235(3) 0.084(8) Uiso 1 1 d . . C15 C 0.67121(13) 0.36245(7) 0.23438(16) 0.0366(3) Uani 1 1 d . . H15 H 0.882(2) 0.5506(12) 1.079(3) 0.087(7) Uiso 1 1 d . . C16 C 0.56595(14) 0.37812(8) 0.30133(18) 0.0407(3) Uani 1 1 d . . H16 H 0.922(3) 0.6405(17) 0.937(4) 0.117(10) Uiso 1 1 d . . C17 C 0.46514(15) 0.34527(8) 0.2518(2) 0.0452(3) Uani 1 1 d . . H17 H 0.881(2) 0.6041(13) 0.760(4) 0.095(9) Uiso 1 1 d . . C18 C 0.47012(15) 0.29647(8) 0.1355(2) 0.0483(4) Uani 1 1 d . . C19 C 0.57355(17) 0.27969(9) 0.0677(2) 0.0560(4) Uani 1 1 d . . C20 C 0.67360(16) 0.31283(9) 0.1172(2) 0.0493(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 0.0406(2) 0.0449(2) 0.03637(19) -0.00600(14) 0.00289(13) 0.00747(15) CL1 0.0690(3) 0.0698(3) 0.0950(4) -0.0182(3) -0.0046(3) -0.0221(3) N1 0.0616(9) 0.0508(8) 0.0366(7) -0.0073(6) -0.0096(6) 0.0189(7) O1 0.0745(8) 0.0464(7) 0.0491(6) -0.0078(5) -0.0086(6) 0.0234(6) C1 0.0372(7) 0.0349(7) 0.0362(7) -0.0004(5) -0.0046(5) 0.0019(5) O2 0.0523(6) 0.0494(6) 0.0380(5) 0.0077(4) -0.0008(4) 0.0123(5) C2 0.0540(10) 0.0439(9) 0.0630(11) 0.0083(8) 0.0049(8) -0.0015(7) C3 0.0908(16) 0.0372(10) 0.0723(13) 0.0112(9) -0.0073(11) -0.0007(9) C4 0.0739(13) 0.0455(10) 0.0830(14) -0.0045(9) -0.0220(11) 0.0213(9) C5 0.0439(10) 0.0619(12) 0.0931(15) -0.0041(11) -0.0065(9) 0.0152(8) C7 0.0316(6) 0.0343(7) 0.0368(7) -0.0006(5) 0.0001(5) -0.0004(5) C6 0.0398(8) 0.0479(10) 0.0663(11) 0.0047(8) 0.0002(7) 0.0034(7) C8 0.0378(7) 0.0332(7) 0.0347(7) -0.0017(5) 0.0007(5) 0.0037(5) C9 0.0388(7) 0.0372(7) 0.0382(7) 0.0017(6) -0.0010(5) 0.0017(6) C10 0.0609(11) 0.0570(11) 0.0536(10) 0.0180(8) -0.0033(8) 0.0158(9) C11 0.0587(13) 0.117(2) 0.0957(18) 0.0282(16) -0.0041(12) 0.0249(13) C12 0.0622(11) 0.0615(11) 0.0351(8) -0.0058(7) -0.0083(7) 0.0086(9) C13 0.0513(9) 0.0755(13) 0.0476(9) -0.0137(9) -0.0031(7) 0.0015(9) C14 0.102(2) 0.0788(17) 0.0819(18) -0.0094(14) 0.0009(14) -0.0210(14) C15 0.0465(8) 0.0331(7) 0.0302(6) -0.0002(5) 0.0001(5) 0.0061(6) C16 0.0511(8) 0.0336(7) 0.0379(7) -0.0050(6) 0.0070(6) 0.0021(6) C17 0.0485(8) 0.0377(8) 0.0498(8) 0.0013(6) 0.0065(7) 0.0012(6) C18 0.0544(9) 0.0380(8) 0.0521(9) 0.0001(7) -0.0043(7) -0.0043(7) C19 0.0674(11) 0.0473(10) 0.0530(10) -0.0189(8) -0.0033(8) 0.0032(8) C20 0.0528(9) 0.0487(9) 0.0463(8) -0.0138(7) 0.0031(7) 0.0110(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 C8 S1 C15 104.61(7) C7 N1 C12 128.01(14) C7 N1 H10 115.0(14) C12 N1 H10 117.0(14) C2 C1 C6 119.42(15) C2 C1 C7 121.18(14) C6 C1 C7 119.36(14) C9 O2 C10 117.19(13) C1 C2 C3 119.97(18) C1 C2 H1 118.5(12) C3 C2 H1 121.6(12) C4 C3 C2 119.99(19) C4 C3 H2 119.7(16) C2 C3 H2 120.2(16) C5 C4 C3 120.47(17) C5 C4 H3 120.3(14) C3 C4 H3 119.2(14) C4 C5 C6 120.02(19) C4 C5 H4 122.2(17) C6 C5 H4 117.7(18) N1 C7 C8 122.14(13) N1 C7 C1 116.53(12) C8 C7 C1 121.30(12) C1 C6 C5 120.12(18) C1 C6 H5 118.2(14) C5 C6 H5 121.7(14) C7 C8 C9 120.70(12) C7 C8 S1 119.31(10) C9 C8 S1 119.92(10) O1 C9 O2 121.72(13) O1 C9 C8 124.42(13) O2 C9 C8 113.86(12) O2 C10 C11 110.48(18) O2 C10 H13 104.4(14) C11 C10 H13 109.4(14) O2 C10 H14 108.3(15) C11 C10 H14 117.2(15) H13 C10 H14 106(2) C10 C11 H11A 109.5 C10 C11 H11B 109.5 H11A C11 H11B 109.5 C10 C11 H11C 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 N1 C12 C13 113.23(16) N1 C12 H11 109.0(13) C13 C12 H11 110.0(13) N1 C12 H12 108.1(13) C13 C12 H12 106.2(13) H11 C12 H12 110.3(18) C14 C13 C12 127.8(2) C14 C13 H15 117.9(14) C12 C13 H15 114.2(14) C13 C14 H16 117.5(19) C13 C14 H17 118.9(17) H16 C14 H17 123(3) C16 C15 C20 118.64(15) C16 C15 S1 124.86(11) C20 C15 S1 116.48(12) C17 C16 C15 120.67(14) C17 C16 H6 118.8(12) C15 C16 H6 120.5(12) C18 C17 C16 119.40(15) C18 C17 H7 121.2(11) C16 C17 H7 119.4(11) C17 C18 C19 121.12(16) C17 C18 CL1 119.15(14) C19 C18 CL1 119.73(13) C18 C19 C20 119.18(15) C18 C19 H8 123.1(13) C20 C19 H8 117.8(13) C19 C20 C15 120.98(16) C19 C20 H9 123.0(13) C15 C20 H9 116.0(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C8 1.7601(14) S1 C15 1.7712(15) CL1 C18 1.7447(17) N1 C7 1.3346(19) N1 C12 1.455(2) N1 H10 0.87(2) O1 C9 1.2219(18) C1 C2 1.381(2) C1 C6 1.384(2) C1 C7 1.4956(19) O2 C9 1.3376(17) O2 C10 1.455(2) C2 C3 1.391(3) C2 H1 0.94(2) C3 C4 1.373(3) C3 H2 0.89(3) C4 C5 1.365(3) C4 H3 1.00(2) C5 C6 1.389(2) C5 H4 0.94(3) C7 C8 1.3892(19) C6 H5 0.94(2) C8 C9 1.4528(19) C10 C11 1.486(3) C10 H13 0.98(2) C10 H14 0.96(3) C11 H11A 0.9600 C11 H11B 0.9600 C11 H11C 0.9600 C12 C13 1.478(3) C12 H11 0.96(2) C12 H12 1.00(2) C13 C14 1.285(4) C13 H15 1.04(3) C14 H16 0.96(3) C14 H17 0.95(3) C15 C16 1.389(2) C15 C20 1.393(2) C16 C17 1.388(2) C16 H6 0.918(19) C17 C18 1.378(2) C17 H7 0.97(2) C18 C19 1.379(3) C19 C20 1.383(3) C19 H8 0.93(2) C20 H9 0.94(2) 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 C6 C1 C2 C3 0.9(3) C7 C1 C2 C3 -176.92(16) C1 C2 C3 C4 -0.3(3) C2 C3 C4 C5 -0.1(3) C3 C4 C5 C6 -0.2(3) C12 N1 C7 C8 -179.36(17) C12 N1 C7 C1 -1.4(3) C2 C1 C7 N1 77.43(19) C6 C1 C7 N1 -100.39(18) C2 C1 C7 C8 -104.59(18) C6 C1 C7 C8 77.59(19) C2 C1 C6 C5 -1.2(3) C7 C1 C6 C5 176.71(17) C4 C5 C6 C1 0.8(3) N1 C7 C8 C9 3.2(2) C1 C7 C8 C9 -174.67(13) N1 C7 C8 S1 -179.81(12) C1 C7 C8 S1 2.32(19) C15 S1 C8 C7 109.90(12) C15 S1 C8 C9 -73.09(13) C10 O2 C9 O1 -2.0(2) C10 O2 C9 C8 177.40(14) C7 C8 C9 O1 -4.0(2) S1 C8 C9 O1 178.99(13) C7 C8 C9 O2 176.57(13) S1 C8 C9 O2 -0.40(18) C9 O2 C10 C11 -85.5(2) C7 N1 C12 C13 135.52(19) N1 C12 C13 C14 -10.0(3) C8 S1 C15 C16 2.27(14) C8 S1 C15 C20 -178.90(12) C20 C15 C16 C17 -0.4(2) S1 C15 C16 C17 178.44(12) C15 C16 C17 C18 0.3(2) C16 C17 C18 C19 0.1(3) C16 C17 C18 CL1 -179.06(12) C17 C18 C19 C20 -0.4(3) CL1 C18 C19 C20 178.77(14) C18 C19 C20 C15 0.3(3) C16 C15 C20 C19 0.1(2) S1 C15 C20 C19 -178.83(14)