#------------------------------------------------------------------------------ #$Date: 2021-10-02 03:46:15 +0300 (Sat, 02 Oct 2021) $ #$Revision: 269447 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158330.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_7158330 loop_ _publ_author_name 'Paysant, Hippolyte' 'Hedir, Siham' 'Justaud, Fr\'ed\'eric' 'Weiswald, Louis Bastien' 'El Dine, Assaad Nasr' 'Soulieman, Ali' 'Hachem, Ali' 'Elie, Nicolas' 'Brotin, Emilie' 'Denoyelle, Christophe' 'Bignon, J\'er\^ome' 'Roussi, Fanny' 'Jouanne, Marie' 'Tasseau, Olivier' 'Roisnel, Thierry' 'Voisin-Chiret, Anne Sophie' 'Gr\'ee, Ren\'e' 'Levoin, Nicolas' 'Poulain, Laurent' _publ_section_title ; Structural revision of the Mcl-1 inhibitor MIM1: synthesis and biological studies on ovarian cancer cells with evaluation of designed analogues ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB01521D _journal_year 2021 _chemical_compound_source 'synthesis as described' _chemical_formula_moiety 'C23 H20 N3 S, Br, H2 O' _chemical_formula_sum 'C23 H22 Br N3 O S' _chemical_formula_weight 468.40 _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 mixed _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_update_record ; 2020-05-29 deposited with the CCDC. 2021-09-16 downloaded from the CCDC. ; _cell_angle_alpha 80.956(4) _cell_angle_beta 81.422(4) _cell_angle_gamma 65.230(4) _cell_formula_units_Z 2 _cell_length_a 9.0870(10) _cell_length_b 10.0635(13) _cell_length_c 13.3909(17) _cell_measurement_reflns_used 9840 _cell_measurement_temperature 150 _cell_measurement_theta_max 27.6809 _cell_measurement_theta_min 2.2413 _cell_measurement_wavelength 0.71073 _cell_volume 1093.3(2) _computing_cell_refinement 'APEX3 (Bruker, 2015)' _computing_data_collection 'SAINT (Bruker, 2014)' _computing_data_reduction 'SAINT (Bruker, 2014)' _computing_molecular_graphics 'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)' _computing_publication_material 'CRYSCALC (T. Roisnel, local program, 2019)' _computing_structure_refinement 'SHELXL-2018_3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT (G. Sheldrick, 2015)' _diffrn_ambient_temperature 150 _diffrn_detector '(CMOS) PHOTON 100' _diffrn_detector_area_resol_mean 10.4167 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.977 _diffrn_measurement_device_type 'D8 VENTURE Bruker AXS' _diffrn_measurement_method 'rotation images' _diffrn_radiation_monochromator 'multilayer monochromator' _diffrn_radiation_probe x-ray _diffrn_radiation_source 'Incoatec microfocus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_unetI/netI 0.0306 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 21379 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.539 _diffrn_reflns_theta_min 2.241 _diffrn_source_current 1.0 _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 1.994 _exptl_absorpt_correction_T_max 0.772 _exptl_absorpt_correction_T_min 0.592 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.423 _exptl_crystal_description prism _exptl_crystal_F_000 480 _exptl_crystal_size_max 0.410 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.130 _refine_diff_density_max 0.311 _refine_diff_density_min -0.436 _refine_diff_density_rms 0.068 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 272 _refine_ls_number_reflns 4926 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.999 _refine_ls_R_factor_all 0.0333 _refine_ls_R_factor_gt 0.0264 _refine_ls_shift/su_max 0.026 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0082P)^2^+1.2468P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0557 _refine_ls_wR_factor_ref 0.0595 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4380 _reflns_number_total 4926 _reflns_threshold_expression >2sigma(I) _cod_data_source_file d1ob01521d2.cif _cod_data_source_block RG13 _cod_database_code 7158330 _shelx_res_file ; TITL import_a.res in P-1 (created by CRYSCALC) job.res created by SHELXL-2018/3 at 16:06:26 on 30-Apr-2019 REM Old TITL RG13 REM SHELXT solution in P-1: R1 0.088, Rweak 0.008, Alpha 0.028 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C23 Br N4 S CELL 0.71073 9.0870 10.0635 13.3909 80.956 81.422 65.230 ZERR 2.000 0.0010 0.0013 0.0017 0.004 0.004 0.004 LATT 1 SFAC C H BR N S O UNIT 46 44 2 6 2 2 MERG 2 FMAP 2 PLAN 20 SIZE 0.13 0.25 0.41 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.008200 1.246800 FVAR 0.47823 MOLE 1 S1 5 0.208697 0.285540 0.475101 11.00000 0.01461 0.02137 = 0.01557 0.00367 -0.00281 -0.01016 C1 1 0.123429 0.413458 0.374322 11.00000 0.01458 0.02052 = 0.01669 0.00222 -0.00544 -0.00747 AFIX 43 H1 2 0.012641 0.447525 0.361761 11.00000 -1.20000 AFIX 0 C2 1 0.230019 0.459230 0.316034 11.00000 0.01308 0.01670 = 0.01590 -0.00185 -0.00366 -0.00560 C3 1 0.195655 0.567057 0.224783 11.00000 0.01695 0.02024 = 0.01569 0.00119 -0.00573 -0.00930 C4 1 0.287640 0.534712 0.131765 11.00000 0.02390 0.02510 = 0.01691 -0.00058 -0.00361 -0.00692 AFIX 43 H4 2 0.378800 0.443196 0.126733 11.00000 -1.20000 AFIX 0 C5 1 0.246083 0.636127 0.046566 11.00000 0.03209 0.03852 = 0.01541 0.00216 -0.00244 -0.01333 AFIX 43 H5 2 0.308360 0.613395 -0.016829 11.00000 -1.20000 AFIX 0 C6 1 0.114134 0.770453 0.053503 11.00000 0.03827 0.03334 = 0.02192 0.01345 -0.01266 -0.01124 AFIX 43 H6 2 0.086098 0.839611 -0.004997 11.00000 -1.20000 AFIX 0 C7 1 0.023579 0.803505 0.145579 11.00000 0.03374 0.02683 = 0.03072 0.00669 -0.00693 0.00054 AFIX 43 H7 2 -0.066272 0.895890 0.150509 11.00000 -1.20000 AFIX 0 C8 1 0.063407 0.702122 0.231046 11.00000 0.02344 0.02648 = 0.02037 0.00140 -0.00233 -0.00301 AFIX 43 H8 2 0.000044 0.725107 0.294089 11.00000 -1.20000 AFIX 0 N9 4 0.387396 0.389896 0.351098 11.00000 0.01157 0.01699 = 0.01272 0.00135 -0.00252 -0.00704 C10 1 0.525730 0.422418 0.306901 11.00000 0.01289 0.02001 = 0.00944 0.00257 -0.00294 -0.00866 C11 1 0.520035 0.561514 0.309805 11.00000 0.01809 0.01877 = 0.01752 -0.00059 -0.00124 -0.00735 AFIX 43 H11 2 0.426776 0.635192 0.340522 11.00000 -1.20000 AFIX 0 C12 1 0.653689 0.591074 0.266814 11.00000 0.02611 0.02250 = 0.01996 0.00300 -0.00234 -0.01523 AFIX 43 H12 2 0.651903 0.685870 0.268044 11.00000 -1.20000 AFIX 0 C13 1 0.789526 0.482981 0.222171 11.00000 0.01738 0.03352 = 0.01356 0.00591 -0.00266 -0.01454 AFIX 43 H13 2 0.879721 0.504297 0.191969 11.00000 -1.20000 AFIX 0 C14 1 0.793648 0.343917 0.221633 11.00000 0.01508 0.02868 = 0.01576 -0.00060 -0.00139 -0.00532 AFIX 43 H14 2 0.887724 0.269484 0.192244 11.00000 -1.20000 AFIX 0 C15 1 0.661069 0.312740 0.263802 11.00000 0.01810 0.01859 = 0.01467 0.00081 -0.00435 -0.00682 AFIX 43 H15 2 0.663210 0.217699 0.263085 11.00000 -1.20000 AFIX 0 C16 1 0.391719 0.297083 0.435380 11.00000 0.01583 0.01565 = 0.01356 0.00064 -0.00287 -0.00737 N17 4 0.524564 0.218037 0.484576 11.00000 0.01524 0.02222 = 0.01495 0.00644 -0.00369 -0.01101 AFIX 2 H17 2 0.611903 0.232926 0.473696 11.00000 -1.20000 AFIX 0 N18 4 0.497898 0.138589 0.574997 11.00000 0.01991 0.01749 = 0.01178 0.00439 -0.00339 -0.00976 C19 1 0.623515 0.064024 0.623632 11.00000 0.01723 0.02003 = 0.01857 0.00378 -0.00296 -0.00839 AFIX 43 H19 2 0.726990 0.060082 0.594437 11.00000 -1.20000 AFIX 0 C20 1 0.609670 -0.015098 0.723507 11.00000 0.02061 0.01666 = 0.01692 0.00337 -0.00406 -0.00676 C21 1 0.746313 -0.079835 0.778231 11.00000 0.02048 0.04559 = 0.02800 0.01526 -0.00759 -0.01097 AFIX 43 H21 2 0.846514 -0.076094 0.748845 11.00000 -1.20000 AFIX 0 C22 1 0.736437 -0.149788 0.875579 11.00000 0.02876 0.04503 = 0.02809 0.01510 -0.01316 -0.01051 AFIX 43 H22 2 0.830803 -0.194024 0.911624 11.00000 -1.20000 AFIX 0 C23 1 0.592865 -0.156449 0.921019 11.00000 0.03669 0.01972 = 0.01761 0.00229 -0.00642 -0.01123 C24 1 0.456883 -0.092444 0.865704 11.00000 0.02909 0.02629 = 0.02132 0.00351 -0.00236 -0.01632 AFIX 43 H24 2 0.357072 -0.096880 0.895252 11.00000 -1.20000 AFIX 0 C25 1 0.464593 -0.022350 0.768257 11.00000 0.02402 0.02156 = 0.02021 0.00402 -0.00711 -0.01163 AFIX 43 H25 2 0.370388 0.020794 0.732055 11.00000 -1.20000 AFIX 0 C26 1 0.583321 -0.230339 1.027517 11.00000 0.05339 0.03024 = 0.01792 0.00537 -0.00721 -0.01877 AFIX 137 H26A 2 0.590548 -0.329619 1.024635 11.00000 -1.50000 H26B 2 0.479675 -0.172792 1.064394 11.00000 -1.50000 H26C 2 0.673545 -0.236583 1.062672 11.00000 -1.50000 AFIX 0 MOLE 2 BR1 3 0.843936 0.282646 0.499737 11.00000 0.01691 0.02746 = 0.01919 0.00226 -0.00389 -0.01307 MOLE 3 O1W 6 0.915167 0.009541 0.351706 11.00000 0.04601 0.02588 = 0.04088 -0.00168 -0.01388 -0.00144 AFIX 2 H1WA 2 0.901108 0.080514 0.385893 11.00000 -1.20000 H1WB 2 0.972969 -0.068115 0.388317 11.00000 -1.20000 AFIX 0 HKLF 4 REM import_a.res in P-1 (created by CRYSCALC) REM wR2 = 0.0595, GooF = S = 0.999, Restrained GooF = 0.999 for all data REM R1 = 0.0264 for 4380 Fo > 4sig(Fo) and 0.0333 for all 4926 data REM 272 parameters refined using 0 restraints END WGHT 0.0153 0.8623 REM Highest difference peak 0.311, deepest hole -0.436, 1-sigma level 0.068 Q1 1 0.5586 -0.1576 1.0743 11.00000 0.05 0.31 Q2 1 0.6158 0.0234 0.6758 11.00000 0.05 0.30 Q3 1 0.6745 -0.3252 1.0341 11.00000 0.05 0.30 Q4 1 0.3769 0.3537 0.3965 11.00000 0.05 0.26 Q5 1 0.4603 0.4017 0.3259 11.00000 0.05 0.25 Q6 1 0.7160 0.5212 0.2530 11.00000 0.05 0.25 Q7 1 0.3144 0.4116 0.3293 11.00000 0.05 0.25 Q8 1 0.4689 -0.0379 0.8336 11.00000 0.05 0.25 Q9 1 0.1590 0.3634 0.4096 11.00000 0.05 0.25 Q10 1 0.5053 -0.2702 1.0340 11.00000 0.05 0.25 Q11 1 0.5414 -0.1405 0.8806 11.00000 0.05 0.24 Q12 1 0.8060 0.4092 0.2436 11.00000 0.05 0.24 Q13 1 0.5833 0.5826 0.2749 11.00000 0.05 0.24 Q14 1 0.6095 0.5640 0.3067 11.00000 0.05 0.24 Q15 1 0.1225 0.6222 0.2203 11.00000 0.05 0.23 Q16 1 0.6679 -0.0312 0.7494 11.00000 0.05 0.23 Q17 1 0.9894 -0.2319 0.7083 11.00000 0.05 0.23 Q18 1 1.0509 0.2987 0.2512 11.00000 0.05 0.23 Q19 1 0.8166 -0.0996 0.5431 11.00000 0.05 0.23 Q20 1 0.3386 0.6832 0.3745 11.00000 0.05 0.23 ; _shelx_res_checksum 35393 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 0.20870(5) 0.28554(5) 0.47510(3) 0.01671(9) Uani 1 1 d . . . . . C1 C 0.1234(2) 0.41346(19) 0.37432(13) 0.0172(3) Uani 1 1 d . . . . . H1 H 0.012641 0.447525 0.361761 0.021 Uiso 1 1 calc R U . . . C2 C 0.2300(2) 0.45923(19) 0.31603(13) 0.0151(3) Uani 1 1 d . . . . . C3 C 0.1957(2) 0.5671(2) 0.22478(13) 0.0169(3) Uani 1 1 d . . . . . C4 C 0.2876(2) 0.5347(2) 0.13177(14) 0.0230(4) Uani 1 1 d . . . . . H4 H 0.378800 0.443196 0.126733 0.028 Uiso 1 1 calc R U . . . C5 C 0.2461(3) 0.6361(2) 0.04657(15) 0.0296(5) Uani 1 1 d . . . . . H5 H 0.308360 0.613395 -0.016829 0.035 Uiso 1 1 calc R U . . . C6 C 0.1141(3) 0.7705(2) 0.05350(16) 0.0331(5) Uani 1 1 d . . . . . H6 H 0.086098 0.839611 -0.004997 0.040 Uiso 1 1 calc R U . . . C7 C 0.0236(3) 0.8035(2) 0.14558(17) 0.0355(5) Uani 1 1 d . . . . . H7 H -0.066272 0.895890 0.150509 0.043 Uiso 1 1 calc R U . . . C8 C 0.0634(2) 0.7021(2) 0.23105(15) 0.0263(4) Uani 1 1 d . . . . . H8 H 0.000044 0.725107 0.294089 0.032 Uiso 1 1 calc R U . . . N9 N 0.38740(17) 0.38990(15) 0.35110(11) 0.0135(3) Uani 1 1 d . . . . . C10 C 0.5257(2) 0.42242(19) 0.30690(12) 0.0137(3) Uani 1 1 d . . . . . C11 C 0.5200(2) 0.5615(2) 0.30980(14) 0.0184(4) Uani 1 1 d . . . . . H11 H 0.426776 0.635192 0.340522 0.022 Uiso 1 1 calc R U . . . C12 C 0.6537(2) 0.5911(2) 0.26681(14) 0.0216(4) Uani 1 1 d . . . . . H12 H 0.651903 0.685870 0.268044 0.026 Uiso 1 1 calc R U . . . C13 C 0.7895(2) 0.4830(2) 0.22217(13) 0.0209(4) Uani 1 1 d . . . . . H13 H 0.879721 0.504297 0.191969 0.025 Uiso 1 1 calc R U . . . C14 C 0.7936(2) 0.3439(2) 0.22163(14) 0.0213(4) Uani 1 1 d . . . . . H14 H 0.887724 0.269484 0.192244 0.026 Uiso 1 1 calc R U . . . C15 C 0.6611(2) 0.3127(2) 0.26380(13) 0.0173(3) Uani 1 1 d . . . . . H15 H 0.663210 0.217699 0.263085 0.021 Uiso 1 1 calc R U . . . C16 C 0.3917(2) 0.29708(19) 0.43538(13) 0.0148(3) Uani 1 1 d . . . . . N17 N 0.52456(19) 0.21804(17) 0.48458(11) 0.0170(3) Uani 1 1 d . . . . . H17 H 0.612(3) 0.233(2) 0.4737(16) 0.020 Uiso 1 1 d . U . . . N18 N 0.49790(18) 0.13859(16) 0.57500(11) 0.0161(3) Uani 1 1 d . . . . . C19 C 0.6235(2) 0.0640(2) 0.62363(14) 0.0189(4) Uani 1 1 d . . . . . H19 H 0.726990 0.060082 0.594437 0.023 Uiso 1 1 calc R U . . . C20 C 0.6097(2) -0.01510(19) 0.72351(14) 0.0187(4) Uani 1 1 d . . . . . C21 C 0.7463(3) -0.0798(3) 0.77823(16) 0.0338(5) Uani 1 1 d . . . . . H21 H 0.846514 -0.076094 0.748845 0.041 Uiso 1 1 calc R U . . . C22 C 0.7364(3) -0.1498(3) 0.87558(17) 0.0365(5) Uani 1 1 d . . . . . H22 H 0.830803 -0.194024 0.911624 0.044 Uiso 1 1 calc R U . . . C23 C 0.5929(3) -0.1564(2) 0.92102(14) 0.0248(4) Uani 1 1 d . . . . . C24 C 0.4569(3) -0.0924(2) 0.86570(15) 0.0245(4) Uani 1 1 d . . . . . H24 H 0.357072 -0.096880 0.895252 0.029 Uiso 1 1 calc R U . . . C25 C 0.4646(2) -0.0223(2) 0.76826(14) 0.0213(4) Uani 1 1 d . . . . . H25 H 0.370388 0.020794 0.732055 0.026 Uiso 1 1 calc R U . . . C26 C 0.5833(3) -0.2303(2) 1.02752(15) 0.0337(5) Uani 1 1 d . . . . . H26A H 0.590548 -0.329619 1.024635 0.051 Uiso 1 1 calc R U . . . H26B H 0.479675 -0.172792 1.064394 0.051 Uiso 1 1 calc R U . . . H26C H 0.673545 -0.236583 1.062672 0.051 Uiso 1 1 calc R U . . . Br1 Br 0.84394(2) 0.28265(2) 0.49974(2) 0.02010(6) Uani 1 1 d . . . . . O1W O 0.9152(2) 0.00954(19) 0.35171(14) 0.0412(4) Uani 1 1 d . . . . . H1WA H 0.901(3) 0.081(3) 0.386(2) 0.049 Uiso 1 1 d . U . . . H1WB H 0.973(4) -0.068(3) 0.388(2) 0.049 Uiso 1 1 d . 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 0.01461(19) 0.0214(2) 0.0156(2) 0.00367(16) -0.00281(16) -0.01016(17) C1 0.0146(8) 0.0205(9) 0.0167(8) 0.0022(7) -0.0054(7) -0.0075(7) C2 0.0131(8) 0.0167(8) 0.0159(8) -0.0019(7) -0.0037(6) -0.0056(7) C3 0.0170(8) 0.0202(9) 0.0157(8) 0.0012(7) -0.0057(7) -0.0093(7) C4 0.0239(9) 0.0251(10) 0.0169(9) -0.0006(7) -0.0036(7) -0.0069(8) C5 0.0321(11) 0.0385(12) 0.0154(9) 0.0022(8) -0.0024(8) -0.0133(10) C6 0.0383(12) 0.0333(11) 0.0219(10) 0.0135(9) -0.0127(9) -0.0112(10) C7 0.0337(11) 0.0268(11) 0.0307(11) 0.0067(9) -0.0069(9) 0.0005(9) C8 0.0234(9) 0.0265(10) 0.0204(9) 0.0014(8) -0.0023(8) -0.0030(8) N9 0.0116(6) 0.0170(7) 0.0127(7) 0.0013(5) -0.0025(5) -0.0070(6) C10 0.0129(7) 0.0200(8) 0.0094(7) 0.0026(6) -0.0029(6) -0.0087(7) C11 0.0181(8) 0.0188(9) 0.0175(8) -0.0006(7) -0.0012(7) -0.0073(7) C12 0.0261(9) 0.0225(9) 0.0200(9) 0.0030(7) -0.0023(8) -0.0152(8) C13 0.0174(8) 0.0335(10) 0.0136(8) 0.0059(7) -0.0027(7) -0.0145(8) C14 0.0151(8) 0.0287(10) 0.0158(8) -0.0006(7) -0.0014(7) -0.0053(8) C15 0.0181(8) 0.0186(9) 0.0147(8) 0.0008(7) -0.0043(7) -0.0068(7) C16 0.0158(8) 0.0156(8) 0.0136(8) 0.0006(6) -0.0029(6) -0.0074(7) N17 0.0152(7) 0.0222(8) 0.0149(7) 0.0064(6) -0.0037(6) -0.0110(6) N18 0.0199(7) 0.0175(7) 0.0118(7) 0.0044(5) -0.0034(6) -0.0098(6) C19 0.0172(8) 0.0200(9) 0.0186(9) 0.0038(7) -0.0030(7) -0.0084(7) C20 0.0206(9) 0.0167(8) 0.0169(8) 0.0034(7) -0.0041(7) -0.0068(7) C21 0.0205(10) 0.0456(13) 0.0280(11) 0.0153(10) -0.0076(8) -0.0110(9) C22 0.0288(11) 0.0450(13) 0.0281(11) 0.0151(10) -0.0132(9) -0.0105(10) C23 0.0367(11) 0.0197(9) 0.0176(9) 0.0023(7) -0.0064(8) -0.0112(8) C24 0.0291(10) 0.0263(10) 0.0213(9) 0.0035(8) -0.0024(8) -0.0163(8) C25 0.0240(9) 0.0216(9) 0.0202(9) 0.0040(7) -0.0071(7) -0.0116(8) C26 0.0534(14) 0.0302(11) 0.0179(10) 0.0054(8) -0.0072(10) -0.0188(11) Br1 0.01691(9) 0.02746(10) 0.01919(9) 0.00226(7) -0.00389(7) -0.01307(7) O1W 0.0460(10) 0.0259(8) 0.0409(10) -0.0017(7) -0.0139(8) -0.0014(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Br Br -0.2901 2.4595 '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' S S 0.1246 0.1234 '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' 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 C16 S1 C1 89.38(8) . . ? C2 C1 S1 113.01(13) . . ? C2 C1 H1 123.5 . . ? S1 C1 H1 123.5 . . ? C1 C2 N9 111.96(15) . . ? C1 C2 C3 126.23(16) . . ? N9 C2 C3 121.80(15) . . ? C8 C3 C4 119.25(17) . . ? C8 C3 C2 118.86(16) . . ? C4 C3 C2 121.83(16) . . ? C5 C4 C3 120.04(18) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C6 C5 C4 120.32(19) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C7 C6 C5 119.86(19) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C6 C7 C8 120.2(2) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C7 C8 C3 120.32(19) . . ? C7 C8 H8 119.8 . . ? C3 C8 H8 119.8 . . ? C16 N9 C2 112.15(14) . . ? C16 N9 C10 122.98(14) . . ? C2 N9 C10 124.71(14) . . ? C15 C10 C11 121.72(17) . . ? C15 C10 N9 118.93(15) . . ? C11 C10 N9 119.35(15) . . ? C10 C11 C12 118.64(17) . . ? C10 C11 H11 120.7 . . ? C12 C11 H11 120.7 . . ? C13 C12 C11 120.40(18) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 119.98(18) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.36(17) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C10 C15 C14 118.89(17) . . ? C10 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? N17 C16 N9 124.53(16) . . ? N17 C16 S1 121.97(13) . . ? N9 C16 S1 113.49(12) . . ? C16 N17 N18 114.68(15) . . ? C16 N17 H17 124.0(15) . . ? N18 N17 H17 118.9(15) . . ? C19 N18 N17 115.38(15) . . ? N18 C19 C20 120.84(17) . . ? N18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C25 C20 C21 118.69(17) . . ? C25 C20 C19 122.91(16) . . ? C21 C20 C19 118.33(17) . . ? C22 C21 C20 120.3(2) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C23 C22 C21 121.52(19) . . ? C23 C22 H22 119.2 . . ? C21 C22 H22 119.2 . . ? C22 C23 C24 117.98(18) . . ? C22 C23 C26 120.89(19) . . ? C24 C23 C26 121.1(2) . . ? C25 C24 C23 121.29(19) . . ? C25 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? C24 C25 C20 120.25(17) . . ? C24 C25 H25 119.9 . . ? C20 C25 H25 119.9 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? H1WA O1W H1WB 104(3) . . ? 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 C16 1.7149(18) . ? S1 C1 1.7346(18) . ? C1 C2 1.340(3) . ? C1 H1 0.9500 . ? C2 N9 1.419(2) . ? C2 C3 1.477(2) . ? C3 C8 1.391(3) . ? C3 C4 1.395(3) . ? C4 C5 1.388(3) . ? C4 H4 0.9500 . ? C5 C6 1.386(3) . ? C5 H5 0.9500 . ? C6 C7 1.380(3) . ? C6 H6 0.9500 . ? C7 C8 1.389(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? N9 C16 1.341(2) . ? N9 C10 1.449(2) . ? C10 C15 1.384(2) . ? C10 C11 1.385(2) . ? C11 C12 1.391(3) . ? C11 H11 0.9500 . ? C12 C13 1.387(3) . ? C12 H12 0.9500 . ? C13 C14 1.385(3) . ? C13 H13 0.9500 . ? C14 C15 1.388(3) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 N17 1.339(2) . ? N17 N18 1.391(2) . ? N17 H17 0.86(2) . ? N18 C19 1.281(2) . ? C19 C20 1.462(2) . ? C19 H19 0.9500 . ? C20 C25 1.391(3) . ? C20 C21 1.395(3) . ? C21 C22 1.390(3) . ? C21 H21 0.9500 . ? C22 C23 1.379(3) . ? C22 H22 0.9500 . ? C23 C24 1.395(3) . ? C23 C26 1.509(3) . ? C24 C25 1.389(3) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? O1W H1WA 0.86(3) . ? O1W H1WB 0.86(3) . ? 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 C16 S1 C1 C2 0.09(14) . . . . ? S1 C1 C2 N9 0.60(19) . . . . ? S1 C1 C2 C3 179.91(14) . . . . ? C1 C2 C3 C8 51.3(3) . . . . ? N9 C2 C3 C8 -129.51(19) . . . . ? C1 C2 C3 C4 -125.9(2) . . . . ? N9 C2 C3 C4 53.3(2) . . . . ? C8 C3 C4 C5 -0.6(3) . . . . ? C2 C3 C4 C5 176.59(18) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C4 C5 C6 C7 0.0(3) . . . . ? C5 C6 C7 C8 -0.6(4) . . . . ? C6 C7 C8 C3 0.6(4) . . . . ? C4 C3 C8 C7 0.0(3) . . . . ? C2 C3 C8 C7 -177.3(2) . . . . ? C1 C2 N9 C16 -1.2(2) . . . . ? C3 C2 N9 C16 179.45(15) . . . . ? C1 C2 N9 C10 -176.66(15) . . . . ? C3 C2 N9 C10 4.0(2) . . . . ? C16 N9 C10 C15 68.0(2) . . . . ? C2 N9 C10 C15 -116.98(18) . . . . ? C16 N9 C10 C11 -111.25(19) . . . . ? C2 N9 C10 C11 63.7(2) . . . . ? C15 C10 C11 C12 0.9(3) . . . . ? N9 C10 C11 C12 -179.84(15) . . . . ? C10 C11 C12 C13 -0.1(3) . . . . ? C11 C12 C13 C14 -1.0(3) . . . . ? C12 C13 C14 C15 1.3(3) . . . . ? C11 C10 C15 C14 -0.6(3) . . . . ? N9 C10 C15 C14 -179.89(15) . . . . ? C13 C14 C15 C10 -0.5(3) . . . . ? C2 N9 C16 N17 -179.64(16) . . . . ? C10 N9 C16 N17 -4.1(3) . . . . ? C2 N9 C16 S1 1.29(18) . . . . ? C10 N9 C16 S1 176.83(12) . . . . ? C1 S1 C16 N17 -179.91(16) . . . . ? C1 S1 C16 N9 -0.80(14) . . . . ? N9 C16 N17 N18 174.78(15) . . . . ? S1 C16 N17 N18 -6.2(2) . . . . ? C16 N17 N18 C19 -179.07(16) . . . . ? N17 N18 C19 C20 175.21(16) . . . . ? N18 C19 C20 C25 4.2(3) . . . . ? N18 C19 C20 C21 -172.48(19) . . . . ? C25 C20 C21 C22 -0.1(3) . . . . ? C19 C20 C21 C22 176.8(2) . . . . ? C20 C21 C22 C23 -0.5(4) . . . . ? C21 C22 C23 C24 0.9(3) . . . . ? C21 C22 C23 C26 -178.8(2) . . . . ? C22 C23 C24 C25 -0.8(3) . . . . ? C26 C23 C24 C25 178.99(18) . . . . ? C23 C24 C25 C20 0.2(3) . . . . ? C21 C20 C25 C24 0.2(3) . . . . ? C19 C20 C25 C24 -176.48(18) . . . . ?