#------------------------------------------------------------------------------ #$Date: 2021-10-02 03:46:15 +0300 (Sat, 02 Oct 2021) $ #$Revision: 269447 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158332.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_7158332 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 'C20 H28 N3 O3 S, Cl' _chemical_formula_sum 'C20 H28 Cl N3 O3 S' _chemical_formula_weight 425.96 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 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 90 _cell_angle_beta 121.156(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.8822(17) _cell_length_b 31.959(6) _cell_length_c 9.896(2) _cell_measurement_reflns_used 9700 _cell_measurement_temperature 150 _cell_measurement_theta_max 27.5257 _cell_measurement_theta_min 2.5493 _cell_measurement_wavelength 0.71073 _cell_volume 2133.3(8) _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 0.995 _diffrn_measured_fraction_theta_max 0.989 _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 0.0406 _diffrn_reflns_av_unetI/netI 0.0346 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 20794 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.533 _diffrn_reflns_theta_min 2.488 _diffrn_source_current 1.0 _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 0.303 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_correction_T_min 0.822 _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 1.326 _exptl_crystal_description prism _exptl_crystal_F_000 904 _exptl_crystal_size_max 0.380 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.060 _refine_diff_density_max 0.369 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.066 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 260 _refine_ls_number_reflns 4862 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.072 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_gt 0.0407 _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0295P)^2^+1.9710P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0929 _refine_ls_wR_factor_ref 0.0972 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4208 _reflns_number_total 4862 _reflns_threshold_expression >2sigma(I) _cod_data_source_file d1ob01521d2.cif _cod_data_source_block JF680 _cod_original_cell_volume 2133.2(8) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7158332 _shelx_res_file ; TITL import_a.res in P2(1)/n (created by CRYSCALC) job.res created by SHELXL-2018/3 at 12:05:04 on 06-May-2019 REM Old TITL JF680 REM SHELXT solution in P2(1)/n: R1 0.123, Rweak 0.007, Alpha 0.027 REM 1.523 for 98 systematic absences, Orientation as input REM Formula found by SHELXT: C20 N4 O2 S Cl CELL 0.71073 7.8822 31.9586 9.8958 90.000 121.156 90.000 ZERR 4.000 0.0017 0.0064 0.0020 0.000 0.007 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O S CL UNIT 80 112 12 12 4 4 MERG 2 FMAP 2 PLAN 20 SIZE 0.06 0.30 0.38 ACTA BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.029500 1.971000 FVAR 0.49803 MOLE 1 S1 5 0.767937 0.416100 0.940422 11.00000 0.01681 0.02414 = 0.01046 0.00088 0.00655 -0.00163 C1 1 0.670019 0.480867 0.438627 11.00000 0.01595 0.01593 = 0.01626 0.00079 0.00935 0.00038 AFIX 23 H1A 2 0.809191 0.484514 0.466473 11.00000 -1.20000 H1B 2 0.634449 0.504408 0.484308 11.00000 -1.20000 AFIX 0 C2 1 0.531264 0.479795 0.258536 11.00000 0.01731 0.02378 = 0.01567 0.00440 0.00856 0.00140 AFIX 23 H2A 2 0.392356 0.476849 0.232163 11.00000 -1.20000 H2B 2 0.542571 0.506410 0.212586 11.00000 -1.20000 AFIX 0 C3 1 0.584448 0.443216 0.187599 11.00000 0.01902 0.03016 = 0.01284 -0.00061 0.00912 -0.00086 AFIX 23 H3A 2 0.487527 0.441918 0.072648 11.00000 -1.20000 H3B 2 0.717131 0.448182 0.202633 11.00000 -1.20000 AFIX 0 C4 1 0.585430 0.401349 0.262383 11.00000 0.02602 0.02305 = 0.01659 -0.00565 0.01129 -0.00227 AFIX 23 H4A 2 0.635872 0.379290 0.221923 11.00000 -1.20000 H4B 2 0.448049 0.393910 0.231504 11.00000 -1.20000 AFIX 0 C5 1 0.715173 0.402943 0.443223 11.00000 0.02356 0.01566 = 0.01633 -0.00005 0.01033 0.00175 AFIX 23 H5A 2 0.703732 0.376321 0.489065 11.00000 -1.20000 H5B 2 0.855829 0.406977 0.475759 11.00000 -1.20000 AFIX 0 C6 1 0.645347 0.439249 0.502279 11.00000 0.01271 0.01642 = 0.01080 0.00057 0.00554 -0.00109 AFIX 13 H6 2 0.499377 0.435265 0.454222 11.00000 -1.20000 AFIX 0 N7 3 0.733128 0.437354 0.676803 11.00000 0.01213 0.01590 = 0.01067 0.00029 0.00581 -0.00169 C8 1 0.922430 0.451536 0.795566 11.00000 0.01243 0.01812 = 0.01527 -0.00006 0.00426 -0.00290 C9 1 1.062945 0.473167 0.760374 11.00000 0.01337 0.03288 = 0.02198 0.00447 0.00492 -0.00765 AFIX 137 H9A 2 1.191340 0.476628 0.858263 11.00000 -1.50000 H9B 2 1.009652 0.500702 0.714319 11.00000 -1.50000 H9C 2 1.080159 0.456384 0.685420 11.00000 -1.50000 AFIX 0 C10 1 0.958912 0.442837 0.940647 11.00000 0.01491 0.02424 = 0.01505 -0.00126 0.00407 -0.00463 AFIX 43 H10 2 1.077978 0.450589 1.034463 11.00000 -1.20000 AFIX 0 C11 1 0.637273 0.417474 0.737752 11.00000 0.01549 0.01380 = 0.01232 -0.00011 0.00797 -0.00002 N12 3 0.460123 0.399106 0.654580 11.00000 0.01372 0.02277 = 0.01010 0.00189 0.00558 -0.00435 AFIX 2 H12 2 0.376550 0.402217 0.551232 11.00000 -1.20000 AFIX 0 N13 3 0.389718 0.381930 0.745850 11.00000 0.01684 0.02253 = 0.01637 0.00320 0.01053 -0.00292 C14 1 0.233524 0.359241 0.669209 11.00000 0.01680 0.01775 = 0.01577 0.00086 0.00838 -0.00078 AFIX 43 H14 2 0.178795 0.354065 0.559793 11.00000 -1.20000 AFIX 0 C15 1 0.140616 0.341463 0.751046 11.00000 0.01719 0.01574 = 0.02028 0.00177 0.01069 -0.00099 C16 1 0.202675 0.352376 0.906227 11.00000 0.02319 0.02204 = 0.02271 -0.00230 0.01409 -0.00663 AFIX 43 H16 2 0.313804 0.370376 0.961955 11.00000 -1.20000 AFIX 0 C17 1 0.107642 0.337836 0.981805 11.00000 0.03280 0.02389 = 0.02580 -0.00164 0.02105 -0.00411 AFIX 43 H17 2 0.155230 0.345201 1.088584 11.00000 -1.20000 AFIX 0 C18 1 -0.058269 0.312330 0.899782 11.00000 0.02949 0.01564 = 0.03564 0.00380 0.02488 -0.00043 C19 1 -0.123029 0.300157 0.744296 11.00000 0.02087 0.01462 = 0.03320 -0.00056 0.01590 -0.00393 C20 1 -0.021772 0.314089 0.671526 11.00000 0.01874 0.01594 = 0.02112 0.00071 0.01011 -0.00116 O21 4 -0.170880 0.298624 0.958865 11.00000 0.03992 0.02599 = 0.04620 -0.00065 0.03571 -0.00753 C22 1 -0.100235 0.308444 1.122055 11.00000 0.06061 0.03257 = 0.04997 0.00010 0.04720 -0.00687 AFIX 137 H22A 2 0.029785 0.295466 1.189651 11.00000 -1.50000 H22B 2 -0.194062 0.297671 1.150521 11.00000 -1.50000 H22C 2 -0.088491 0.338856 1.136723 11.00000 -1.50000 AFIX 0 O23 4 -0.284222 0.274072 0.664857 11.00000 0.02458 0.01807 = 0.04593 -0.00330 0.02092 -0.00771 C24 1 -0.462905 0.295347 0.561922 11.00000 0.01990 0.02605 = 0.13019 -0.00655 0.01491 -0.00448 AFIX 137 H24A 2 -0.493682 0.314807 0.622844 11.00000 -1.50000 H24B 2 -0.570788 0.275011 0.508167 11.00000 -1.50000 H24C 2 -0.448098 0.310970 0.483408 11.00000 -1.50000 AFIX 0 O25 4 -0.085304 0.303454 0.517780 11.00000 0.03301 0.02376 = 0.02259 -0.00381 0.01263 -0.01065 C26 1 -0.083634 0.259676 0.487145 11.00000 0.05523 0.03179 = 0.03703 -0.00691 0.02490 0.00266 AFIX 137 H26A 2 -0.015698 0.244366 0.587379 11.00000 -1.50000 H26B 2 -0.013840 0.255200 0.430261 11.00000 -1.50000 H26C 2 -0.220223 0.249524 0.422845 11.00000 -1.50000 AFIX 0 MOLE 2 CL1 6 0.122469 0.413121 0.317913 11.00000 0.01603 0.03652 = 0.01456 0.00469 0.00385 -0.00306 HKLF 4 REM import_a.res in P2(1)/n (created by CRYSCALC) REM wR2 = 0.0972, GooF = S = 1.072, Restrained GooF = 1.072 for all data REM R1 = 0.0407 for 4208 Fo > 4sig(Fo) and 0.0496 for all 4862 data REM 260 parameters refined using 0 restraints END WGHT 0.0325 1.7987 REM Highest difference peak 0.369, deepest hole -0.276, 1-sigma level 0.066 Q1 1 -0.1107 0.2391 0.5350 11.00000 0.05 0.37 Q2 1 0.6817 0.4602 0.4801 11.00000 0.05 0.37 Q3 1 0.9890 0.4644 0.7794 11.00000 0.05 0.32 Q4 1 0.6945 0.4225 0.4864 11.00000 0.05 0.32 Q5 1 0.6982 0.4436 0.5964 11.00000 0.05 0.31 Q6 1 0.9336 0.4564 0.8782 11.00000 0.05 0.31 Q7 1 0.8694 0.4347 0.9389 11.00000 0.05 0.31 Q8 1 -0.4559 0.3256 0.5535 11.00000 0.05 0.30 Q9 1 -0.1328 0.2556 0.3592 11.00000 0.05 0.30 Q10 1 0.1171 0.2610 0.5608 11.00000 0.05 0.29 Q11 1 0.5583 0.4620 0.2187 11.00000 0.05 0.29 Q12 1 0.4202 0.3880 0.7012 11.00000 0.05 0.27 Q13 1 0.1442 0.3856 0.2986 11.00000 0.05 0.27 Q14 1 0.3962 0.4074 0.1821 11.00000 0.05 0.27 Q15 1 0.8398 0.4463 0.7345 11.00000 0.05 0.26 Q16 1 0.9568 0.4319 0.8618 11.00000 0.05 0.25 Q17 1 0.0262 0.3283 0.9313 11.00000 0.05 0.25 Q18 1 0.5500 0.4217 0.2083 11.00000 0.05 0.24 Q19 1 0.7973 0.3994 1.0142 11.00000 0.05 0.24 Q20 1 0.2957 0.4202 0.4392 11.00000 0.05 0.24 ; _shelx_res_checksum 71340 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 0.76794(6) 0.41610(2) 0.94042(5) 0.01738(10) Uani 1 1 d . . . . . C1 C 0.6700(2) 0.48087(5) 0.43863(19) 0.0156(3) Uani 1 1 d . . . . . H1A H 0.809191 0.484514 0.466473 0.019 Uiso 1 1 calc R U . . . H1B H 0.634449 0.504408 0.484308 0.019 Uiso 1 1 calc R U . . . C2 C 0.5313(3) 0.47980(6) 0.2585(2) 0.0189(3) Uani 1 1 d . . . . . H2A H 0.392356 0.476849 0.232163 0.023 Uiso 1 1 calc R U . . . H2B H 0.542571 0.506410 0.212586 0.023 Uiso 1 1 calc R U . . . C3 C 0.5844(3) 0.44322(6) 0.1876(2) 0.0203(4) Uani 1 1 d . . . . . H3A H 0.487527 0.441918 0.072648 0.024 Uiso 1 1 calc R U . . . H3B H 0.717131 0.448182 0.202633 0.024 Uiso 1 1 calc R U . . . C4 C 0.5854(3) 0.40135(6) 0.2624(2) 0.0218(4) Uani 1 1 d . . . . . H4A H 0.635872 0.379290 0.221923 0.026 Uiso 1 1 calc R U . . . H4B H 0.448049 0.393910 0.231504 0.026 Uiso 1 1 calc R U . . . C5 C 0.7152(3) 0.40294(5) 0.4432(2) 0.0185(3) Uani 1 1 d . . . . . H5A H 0.703732 0.376321 0.489065 0.022 Uiso 1 1 calc R U . . . H5B H 0.855829 0.406977 0.475759 0.022 Uiso 1 1 calc R U . . . C6 C 0.6453(2) 0.43925(5) 0.50228(18) 0.0136(3) Uani 1 1 d . . . . . H6 H 0.499377 0.435265 0.454222 0.016 Uiso 1 1 calc R U . . . N7 N 0.7331(2) 0.43735(4) 0.67680(15) 0.0129(3) Uani 1 1 d . . . . . C8 C 0.9224(2) 0.45154(5) 0.79557(19) 0.0166(3) Uani 1 1 d . . . . . C9 C 1.0629(3) 0.47317(6) 0.7604(2) 0.0247(4) Uani 1 1 d . . . . . H9A H 1.191340 0.476628 0.858263 0.037 Uiso 1 1 calc R U . . . H9B H 1.009652 0.500702 0.714319 0.037 Uiso 1 1 calc R U . . . H9C H 1.080159 0.456384 0.685420 0.037 Uiso 1 1 calc R U . . . C10 C 0.9589(3) 0.44284(5) 0.9406(2) 0.0198(4) Uani 1 1 d . . . . . H10 H 1.077978 0.450589 1.034463 0.024 Uiso 1 1 calc R U . . . C11 C 0.6373(2) 0.41747(5) 0.73775(18) 0.0135(3) Uani 1 1 d . . . . . N12 N 0.4601(2) 0.39911(5) 0.65458(16) 0.0158(3) Uani 1 1 d . . . . . H12 H 0.377(3) 0.4022(6) 0.551(3) 0.019 Uiso 1 1 d . U . . . N13 N 0.3897(2) 0.38193(5) 0.74585(17) 0.0177(3) Uani 1 1 d . . . . . C14 C 0.2335(2) 0.35924(5) 0.6692(2) 0.0168(3) Uani 1 1 d . . . . . H14 H 0.178795 0.354065 0.559793 0.020 Uiso 1 1 calc R U . . . C15 C 0.1406(3) 0.34146(5) 0.7510(2) 0.0173(3) Uani 1 1 d . . . . . C16 C 0.2027(3) 0.35238(6) 0.9062(2) 0.0216(4) Uani 1 1 d . . . . . H16 H 0.313804 0.370376 0.961955 0.026 Uiso 1 1 calc R U . . . C17 C 0.1076(3) 0.33784(6) 0.9818(2) 0.0247(4) Uani 1 1 d . . . . . H17 H 0.155230 0.345201 1.088584 0.030 Uiso 1 1 calc R U . . . C18 C -0.0583(3) 0.31233(5) 0.8998(2) 0.0231(4) Uani 1 1 d . . . . . C19 C -0.1230(3) 0.30016(5) 0.7443(2) 0.0220(4) Uani 1 1 d . . . . . C20 C -0.0218(3) 0.31409(5) 0.6715(2) 0.0187(3) Uani 1 1 d . . . . . O21 O -0.1709(2) 0.29862(4) 0.95887(18) 0.0310(3) Uani 1 1 d . . . . . C22 C -0.1002(4) 0.30844(7) 1.1221(3) 0.0390(5) Uani 1 1 d . . . . . H22A H 0.029785 0.295466 1.189651 0.058 Uiso 1 1 calc R U . . . H22B H -0.194062 0.297671 1.150521 0.058 Uiso 1 1 calc R U . . . H22C H -0.088491 0.338856 1.136723 0.058 Uiso 1 1 calc R U . . . O23 O -0.2842(2) 0.27407(4) 0.66486(18) 0.0283(3) Uani 1 1 d . . . . . C24 C -0.4629(4) 0.29535(8) 0.5619(4) 0.0700(11) Uani 1 1 d . . . . . H24A H -0.493682 0.314807 0.622844 0.105 Uiso 1 1 calc R U . . . H24B H -0.570788 0.275011 0.508167 0.105 Uiso 1 1 calc R U . . . H24C H -0.448098 0.310970 0.483408 0.105 Uiso 1 1 calc R U . . . O25 O -0.0853(2) 0.30345(4) 0.51778(15) 0.0273(3) Uani 1 1 d . . . . . C26 C -0.0836(4) 0.25968(7) 0.4871(3) 0.0409(5) Uani 1 1 d . . . . . H26A H -0.015698 0.244366 0.587379 0.061 Uiso 1 1 calc R U . . . H26B H -0.013840 0.255200 0.430261 0.061 Uiso 1 1 calc R U . . . H26C H -0.220223 0.249524 0.422845 0.061 Uiso 1 1 calc R U . . . Cl1 Cl 0.12247(6) 0.41312(2) 0.31791(5) 0.02428(11) 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 0.0168(2) 0.0241(2) 0.01046(19) 0.00088(15) 0.00655(16) -0.00163(16) C1 0.0160(8) 0.0159(8) 0.0163(8) 0.0008(6) 0.0094(7) 0.0004(6) C2 0.0173(8) 0.0238(8) 0.0157(8) 0.0044(6) 0.0086(7) 0.0014(7) C3 0.0190(8) 0.0302(9) 0.0128(8) -0.0006(7) 0.0091(7) -0.0009(7) C4 0.0260(9) 0.0230(9) 0.0166(8) -0.0056(7) 0.0113(7) -0.0023(7) C5 0.0236(9) 0.0157(8) 0.0163(8) 0.0000(6) 0.0103(7) 0.0018(6) C6 0.0127(7) 0.0164(8) 0.0108(7) 0.0006(6) 0.0055(6) -0.0011(6) N7 0.0121(6) 0.0159(6) 0.0107(6) 0.0003(5) 0.0058(5) -0.0017(5) C8 0.0124(8) 0.0181(8) 0.0153(8) -0.0001(6) 0.0043(6) -0.0029(6) C9 0.0134(8) 0.0329(10) 0.0220(9) 0.0045(7) 0.0049(7) -0.0077(7) C10 0.0149(8) 0.0242(9) 0.0151(8) -0.0013(6) 0.0041(7) -0.0046(7) C11 0.0155(8) 0.0138(7) 0.0123(7) -0.0001(6) 0.0080(6) 0.0000(6) N12 0.0137(7) 0.0228(7) 0.0101(7) 0.0019(5) 0.0056(6) -0.0043(5) N13 0.0168(7) 0.0225(7) 0.0164(7) 0.0032(5) 0.0105(6) -0.0029(6) C14 0.0168(8) 0.0178(8) 0.0158(8) 0.0009(6) 0.0084(7) -0.0008(6) C15 0.0172(8) 0.0157(8) 0.0203(8) 0.0018(6) 0.0107(7) -0.0010(6) C16 0.0232(9) 0.0220(9) 0.0227(9) -0.0023(7) 0.0141(8) -0.0066(7) C17 0.0328(10) 0.0239(9) 0.0258(9) -0.0016(7) 0.0210(9) -0.0041(8) C18 0.0295(10) 0.0156(8) 0.0356(10) 0.0038(7) 0.0249(9) -0.0004(7) C19 0.0209(9) 0.0146(8) 0.0332(10) -0.0006(7) 0.0159(8) -0.0039(7) C20 0.0187(9) 0.0159(8) 0.0211(8) 0.0007(6) 0.0101(7) -0.0012(6) O21 0.0399(8) 0.0260(7) 0.0462(9) -0.0006(6) 0.0357(8) -0.0075(6) C22 0.0606(16) 0.0326(11) 0.0500(14) 0.0001(10) 0.0472(13) -0.0069(10) O23 0.0246(7) 0.0181(6) 0.0459(9) -0.0033(6) 0.0209(7) -0.0077(5) C24 0.0199(12) 0.0260(12) 0.130(3) -0.0065(15) 0.0149(15) -0.0045(9) O25 0.0330(8) 0.0238(7) 0.0226(7) -0.0038(5) 0.0126(6) -0.0106(6) C26 0.0552(15) 0.0318(11) 0.0370(12) -0.0069(9) 0.0249(12) 0.0027(10) Cl1 0.0160(2) 0.0365(3) 0.0146(2) 0.00469(17) 0.00385(16) -0.00306(17) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 S1 C10 89.12(8) . . ? C6 C1 C2 107.05(13) . . ? C6 C1 H1A 110.3 . . ? C2 C1 H1A 110.3 . . ? C6 C1 H1B 110.3 . . ? C2 C1 H1B 110.3 . . ? H1A C1 H1B 108.6 . . ? C3 C2 C1 110.49(14) . . ? C3 C2 H2A 109.6 . . ? C1 C2 H2A 109.6 . . ? C3 C2 H2B 109.6 . . ? C1 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C4 C3 C2 112.40(14) . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? C3 C4 C5 111.66(14) . . ? C3 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? C3 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? C6 C5 C4 108.50(14) . . ? C6 C5 H5A 110.0 . . ? C4 C5 H5A 110.0 . . ? C6 C5 H5B 110.0 . . ? C4 C5 H5B 110.0 . . ? H5A C5 H5B 108.4 . . ? N7 C6 C5 111.68(13) . . ? N7 C6 C1 115.53(13) . . ? C5 C6 C1 110.90(14) . . ? N7 C6 H6 106.0 . . ? C5 C6 H6 106.0 . . ? C1 C6 H6 106.0 . . ? C11 N7 C8 112.01(13) . . ? C11 N7 C6 120.41(13) . . ? C8 N7 C6 127.36(13) . . ? C10 C8 N7 111.93(15) . . ? C10 C8 C9 124.95(16) . . ? N7 C8 C9 123.11(15) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 S1 113.39(13) . . ? C8 C10 H10 123.3 . . ? S1 C10 H10 123.3 . . ? N12 C11 N7 125.60(15) . . ? N12 C11 S1 120.85(12) . . ? N7 C11 S1 113.53(12) . . ? C11 N12 N13 114.43(13) . . ? C11 N12 H12 125.1(13) . . ? N13 N12 H12 118.8(14) . . ? C14 N13 N12 114.89(14) . . ? N13 C14 C15 119.67(16) . . ? N13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C16 C15 C20 118.09(16) . . ? C16 C15 C14 121.56(16) . . ? C20 C15 C14 120.28(16) . . ? C17 C16 C15 122.13(17) . . ? C17 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? C16 C17 C18 119.31(17) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? O21 C18 C17 124.20(18) . . ? O21 C18 C19 115.67(17) . . ? C17 C18 C19 120.09(17) . . ? O23 C19 C20 120.26(17) . . ? O23 C19 C18 119.95(16) . . ? C20 C19 C18 119.79(16) . . ? O25 C20 C19 120.90(16) . . ? O25 C20 C15 118.51(16) . . ? C19 C20 C15 120.48(16) . . ? C18 O21 C22 116.73(16) . . ? O21 C22 H22A 109.5 . . ? O21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C19 O23 C24 113.67(15) . . ? O23 C24 H24A 109.5 . . ? O23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C20 O25 C26 115.93(15) . . ? O25 C26 H26A 109.5 . . ? O25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? O25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 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 C11 1.7169(16) . ? S1 C10 1.7299(18) . ? C1 C6 1.527(2) . ? C1 C2 1.535(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.530(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.527(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.535(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.524(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N7 1.4929(19) . ? C6 H6 1.0000 . ? N7 C11 1.345(2) . ? N7 C8 1.414(2) . ? C8 C10 1.339(2) . ? C8 C9 1.492(2) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10 0.9500 . ? C11 N12 1.335(2) . ? N12 N13 1.3942(19) . ? N12 H12 0.89(2) . ? N13 C14 1.285(2) . ? C14 C15 1.459(2) . ? C14 H14 0.9500 . ? C15 C16 1.393(2) . ? C15 C20 1.407(2) . ? C16 C17 1.384(3) . ? C16 H16 0.9500 . ? C17 C18 1.391(3) . ? C17 H17 0.9500 . ? C18 O21 1.363(2) . ? C18 C19 1.402(3) . ? C19 O23 1.376(2) . ? C19 C20 1.396(3) . ? C20 O25 1.376(2) . ? O21 C22 1.444(3) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? O23 C24 1.414(3) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? O25 C26 1.433(2) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 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 C6 C1 C2 C3 -59.43(18) . . . . ? C1 C2 C3 C4 54.87(19) . . . . ? C2 C3 C4 C5 -52.3(2) . . . . ? C3 C4 C5 C6 54.60(19) . . . . ? C4 C5 C6 N7 167.52(13) . . . . ? C4 C5 C6 C1 -62.07(18) . . . . ? C2 C1 C6 N7 -167.17(13) . . . . ? C2 C1 C6 C5 64.47(17) . . . . ? C5 C6 N7 C11 -91.67(18) . . . . ? C1 C6 N7 C11 140.36(15) . . . . ? C5 C6 N7 C8 82.48(19) . . . . ? C1 C6 N7 C8 -45.5(2) . . . . ? C11 N7 C8 C10 -1.8(2) . . . . ? C6 N7 C8 C10 -176.33(15) . . . . ? C11 N7 C8 C9 177.67(16) . . . . ? C6 N7 C8 C9 3.1(3) . . . . ? N7 C8 C10 S1 1.3(2) . . . . ? C9 C8 C10 S1 -178.17(15) . . . . ? C11 S1 C10 C8 -0.36(15) . . . . ? C8 N7 C11 N12 -176.83(15) . . . . ? C6 N7 C11 N12 -1.8(2) . . . . ? C8 N7 C11 S1 1.51(17) . . . . ? C6 N7 C11 S1 176.50(11) . . . . ? C10 S1 C11 N12 177.74(15) . . . . ? C10 S1 C11 N7 -0.68(13) . . . . ? N7 C11 N12 N13 -177.79(15) . . . . ? S1 C11 N12 N13 4.0(2) . . . . ? C11 N12 N13 C14 -170.75(15) . . . . ? N12 N13 C14 C15 -176.78(14) . . . . ? N13 C14 C15 C16 7.7(3) . . . . ? N13 C14 C15 C20 -175.35(16) . . . . ? C20 C15 C16 C17 -1.3(3) . . . . ? C14 C15 C16 C17 175.76(17) . . . . ? C15 C16 C17 C18 -1.6(3) . . . . ? C16 C17 C18 O21 -175.35(18) . . . . ? C16 C17 C18 C19 2.6(3) . . . . ? O21 C18 C19 O23 -3.5(3) . . . . ? C17 C18 C19 O23 178.37(17) . . . . ? O21 C18 C19 C20 177.43(16) . . . . ? C17 C18 C19 C20 -0.7(3) . . . . ? O23 C19 C20 O25 2.6(3) . . . . ? C18 C19 C20 O25 -178.35(16) . . . . ? O23 C19 C20 C15 178.67(16) . . . . ? C18 C19 C20 C15 -2.3(3) . . . . ? C16 C15 C20 O25 179.39(16) . . . . ? C14 C15 C20 O25 2.3(2) . . . . ? C16 C15 C20 C19 3.2(3) . . . . ? C14 C15 C20 C19 -173.86(16) . . . . ? C17 C18 O21 C22 -5.8(3) . . . . ? C19 C18 O21 C22 176.11(17) . . . . ? C20 C19 O23 C24 -82.4(3) . . . . ? C18 C19 O23 C24 98.6(3) . . . . ? C19 C20 O25 C26 -62.5(2) . . . . ? C15 C20 O25 C26 121.36(19) . . . . ?