#------------------------------------------------------------------------------ #$Date: 2021-01-09 07:32:57 +0200 (Sat, 09 Jan 2021) $ #$Revision: 260880 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/20/7242057.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_7242057 loop_ _publ_author_name 'Bangade, V. M.' 'Mali, P. R.' 'Meshram, H. M.' _publ_section_title ; Solid-phase reactive chromatography (SPRC): a sustainable method for the synthesis of benzimidazol-diphenyl-2-imino-thiazolidine-4-ols (hemiaminals) which are active against lung cancer ; _journal_issue 4 _journal_name_full 'RSC Advances' _journal_page_first 2320 _journal_page_last 2324 _journal_paper_doi 10.1039/D0RA09082D _journal_volume 11 _journal_year 2021 _chemical_formula_moiety '0.67(Br), 0.67(C23 H19 Br Cl N4 O S), 0.67(H2 O), 0.67(C H4 O)' _chemical_formula_sum 'C16 H16.67 Br1.33 Cl0.67 N2.67 O2 S0.67' _chemical_formula_weight 429.87 _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 _audit_creation_date 2014-12-27 _audit_creation_method ; Olex2 1.2 (compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4973) ; _audit_update_record ; 2014-12-27 deposited with the CCDC. 2020-11-30 downloaded from the CCDC. ; _cell_angle_alpha 71.877(10) _cell_angle_beta 79.537(9) _cell_angle_gamma 78.741(10) _cell_formula_units_Z 3 _cell_length_a 7.9404(8) _cell_length_b 11.6089(14) _cell_length_c 15.7240(18) _cell_measurement_reflns_used 3295 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 70.7207 _cell_measurement_theta_min 2.9798 _cell_volume 1339.6(3) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.1293 _diffrn_measured_fraction_theta_full 0.957 _diffrn_measured_fraction_theta_max 0.936 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -51.00 35.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - -33.5000 57.0000 -150.0000 86 #__ type_ start__ end____ width___ exp.time_ 2 omega -67.00 -41.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - -33.5000 125.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 3 omega -66.00 32.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - -33.5000 19.0000 150.0000 98 #__ type_ start__ end____ width___ exp.time_ 4 omega -85.00 -36.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - -33.5000 -50.0000 -60.0000 49 #__ type_ start__ end____ width___ exp.time_ 5 omega 25.00 104.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - 54.0000 -125.0000 -60.0000 79 #__ type_ start__ end____ width___ exp.time_ 6 omega 82.00 115.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - 54.0000 77.0000 90.0000 33 #__ type_ start__ end____ width___ exp.time_ 7 omega 11.00 58.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - 54.0000 -57.0000 120.0000 47 #__ type_ start__ end____ width___ exp.time_ 8 omega 53.00 113.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - 54.0000 57.0000 -120.0000 60 #__ type_ start__ end____ width___ exp.time_ 9 omega 25.00 71.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - 54.0000 77.0000 90.0000 46 #__ type_ start__ end____ width___ exp.time_ 10 omega 77.00 105.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - 54.0000 38.0000 -180.0000 28 #__ type_ start__ end____ width___ exp.time_ 11 omega -12.00 68.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - 54.0000 -57.0000 -30.0000 80 #__ type_ start__ end____ width___ exp.time_ 12 omega 37.00 111.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 -120.0000 74 #__ type_ start__ end____ width___ exp.time_ 13 omega 45.00 90.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - 108.0000 -38.0000 -120.0000 45 #__ type_ start__ end____ width___ exp.time_ 14 omega 40.00 92.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - 108.0000 -38.0000 30.0000 52 #__ type_ start__ end____ width___ exp.time_ 15 omega 44.00 88.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - 108.0000 -38.0000 -30.0000 44 #__ type_ start__ end____ width___ exp.time_ 16 omega 41.00 132.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - 108.0000 -91.0000 -90.0000 91 #__ type_ start__ end____ width___ exp.time_ 17 omega 37.00 75.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - 108.0000 -38.0000 90.0000 38 #__ type_ start__ end____ width___ exp.time_ 18 omega 65.00 92.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - 108.0000 -25.0000 90.0000 27 #__ type_ start__ end____ width___ exp.time_ 19 omega 48.00 113.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 90.0000 65 #__ type_ start__ end____ width___ exp.time_ 20 omega 97.00 164.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - 108.0000 50.0000 0.0000 67 #__ type_ start__ end____ width___ exp.time_ 21 omega 63.00 96.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - 108.0000 -50.0000 -90.0000 33 #__ type_ start__ end____ width___ exp.time_ 22 omega 50.00 94.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - 108.0000 -25.0000 -180.0000 44 #__ type_ start__ end____ width___ exp.time_ 23 omega 38.00 64.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - 108.0000 -38.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 24 omega 45.00 176.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - 108.0000 -12.0000 -30.0000 131 #__ type_ start__ end____ width___ exp.time_ 25 omega 36.00 63.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - 108.0000 -25.0000 -60.0000 27 #__ type_ start__ end____ width___ exp.time_ 26 omega 51.00 116.00 1.0000 3.9700 omega____ theta____ kappa____ phi______ frames - 108.0000 -77.0000 90.0000 65 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.1247698000 _diffrn_orient_matrix_UB_12 -0.0441220000 _diffrn_orient_matrix_UB_13 0.0719801000 _diffrn_orient_matrix_UB_21 0.1421526000 _diffrn_orient_matrix_UB_22 0.0623332000 _diffrn_orient_matrix_UB_23 -0.0696173000 _diffrn_orient_matrix_UB_31 -0.0634719000 _diffrn_orient_matrix_UB_32 0.1187633000 _diffrn_orient_matrix_UB_33 0.0279572000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_unetI/netI 0.0546 _diffrn_reflns_Laue_measured_fraction_full 0.957 _diffrn_reflns_Laue_measured_fraction_max 0.936 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 8394 _diffrn_reflns_point_group_measured_fraction_full 0.957 _diffrn_reflns_point_group_measured_fraction_max 0.936 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 70.857 _diffrn_reflns_theta_min 2.982 _diffrn_source 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 5.761 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.61265 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.599 _exptl_crystal_description plate _exptl_crystal_F_000 648 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.713 _refine_diff_density_min -1.292 _refine_diff_density_rms 0.129 _refine_ls_extinction_coef 0.0015(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.192 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 324 _refine_ls_number_reflns 4826 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.192 _refine_ls_R_factor_all 0.0874 _refine_ls_R_factor_gt 0.0640 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1045P)^2^+2.8972P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1851 _refine_ls_wR_factor_ref 0.2408 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3624 _reflns_number_total 4826 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra09082d2.cif _cod_data_source_block HMM-7-OH _cod_database_code 7242057 _shelxl_version_number 2014-3 _chemical_oxdiff_formula 'C24 H26 N3 S' _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 0.893 _shelx_estimated_absorpt_t_min 0.277 _reflns_odcompleteness_completeness 96.02 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups, All O(H,H) groups 2.a Free rotating group: O1W(H1WA,H1WB) 2.b Secondary CH2 refined with riding coordinates: C8(H8A,H8B) 2.c Aromatic/amide H refined with riding coordinates: N1(H1A), N2(H2), C14(H14), C21(H21), C22(H22), C18(H18), C2(H2A), C13(H13), C19(H19), C11(H11), C1(H1B), C4(H4), C3(H3) 2.d Idealised Me refined as rotating group: C16(H16A,H16B,H16C), C1S(H1SA,H1SB,H1SC) 2.e Idealised tetrahedral OH refined as rotating group: O1(H1), O1S(H1S) ; _shelx_res_file ; TITL CELL 1.54184 7.940373 11.60885 15.723959 71.8765 79.5366 78.7407 ZERR 3 0.000845 0.001388 0.001793 0.0104 0.0092 0.0095 LATT 1 SFAC C H N S Br Cl O UNIT 48 50 8 2 4 2 6 L.S. 4 PLAN 10 SIZE 0.02 0.25 0.3 BOND $H CONF HTAB ACTA fmap 2 REM REM REM WGHT 0.104500 2.897200 EXTI 0.001477 FVAR 5.21221 BR1C 5 0.314209 0.516528 0.170566 11.00000 0.06221 0.05345 = 0.07474 -0.01721 -0.00537 -0.00408 BR1 5 0.288583 0.567473 0.394748 11.00000 0.08117 0.08911 = 0.07177 -0.02613 -0.01590 0.00176 S1 4 0.067567 0.644619 0.934974 11.00000 0.07257 0.04583 = 0.05512 -0.00267 -0.00981 -0.00318 CL1 6 0.257369 1.183780 0.569032 11.00000 0.15858 0.09165 = 0.11781 0.00842 -0.00747 -0.08164 O1 7 0.363678 0.718023 0.772027 11.00000 0.04514 0.05629 = 0.08109 -0.01842 -0.01278 -0.00678 AFIX 147 H1 2 0.442107 0.660094 0.782682 11.00000 -1.50000 AFIX 6 O1W 7 0.403599 0.375122 0.012986 11.00000 0.10943 0.09395 = 0.08224 -0.04085 0.01572 -0.05470 H1WA 2 0.374869 0.397209 0.061000 11.00000 -1.50000 H1WB 2 0.513383 0.360810 0.002496 11.00000 -1.50000 AFIX 0 N4 3 0.070843 0.776461 0.768461 11.00000 0.04636 0.04100 = 0.05213 -0.00496 -0.00327 -0.00731 N1 3 -0.196532 0.989287 0.973772 11.00000 0.06264 0.03971 = 0.07377 -0.01394 -0.01847 -0.00297 AFIX 43 H1A 2 -0.149462 1.053718 0.945309 11.00000 -1.20000 AFIX 0 C10 1 0.038670 0.885032 0.694143 11.00000 0.04608 0.03904 = 0.05557 -0.00703 -0.00156 -0.00653 N3 3 -0.084254 0.883134 0.866668 11.00000 0.05724 0.04013 = 0.06970 -0.00387 -0.01262 -0.00804 N2 3 -0.265730 0.806777 1.006269 11.00000 0.05899 0.04883 = 0.05662 -0.01471 -0.00663 -0.01394 AFIX 43 H2 2 -0.271206 0.735390 1.002319 11.00000 -1.20000 AFIX 0 C20 1 0.270819 0.595054 0.505866 11.00000 0.05701 0.05488 = 0.06981 -0.01929 -0.01258 0.00373 C15 1 -0.112005 0.907341 0.655635 11.00000 0.05520 0.04718 = 0.05061 -0.01717 -0.00745 -0.00246 C9 1 0.213858 0.675934 0.762553 11.00000 0.04298 0.03943 = 0.06044 -0.00814 -0.00917 -0.00309 C14 1 -0.148731 1.019586 0.592033 11.00000 0.07069 0.05551 = 0.06235 -0.01115 -0.01642 0.00558 AFIX 43 H14 2 -0.251128 1.037561 0.566572 11.00000 -1.20000 AFIX 0 C5 1 -0.351771 0.857148 1.076941 11.00000 0.04999 0.05904 = 0.06423 -0.02067 -0.01277 -0.00662 C21 1 0.373619 0.667035 0.521869 11.00000 0.05816 0.08365 = 0.06201 -0.02378 -0.00445 -0.01594 AFIX 43 H21 2 0.457023 0.700726 0.475935 11.00000 -1.20000 AFIX 0 C8 1 0.164072 0.572683 0.847725 11.00000 0.06170 0.04385 = 0.05921 -0.00565 -0.00795 -0.00412 AFIX 23 H8A 2 0.266027 0.514775 0.865891 11.00000 -1.20000 H8B 2 0.082337 0.529094 0.836006 11.00000 -1.20000 AFIX 0 C22 1 0.356534 0.690419 0.603491 11.00000 0.05014 0.07415 = 0.08138 -0.00986 -0.01097 -0.02252 AFIX 43 H22 2 0.430073 0.738431 0.611495 11.00000 -1.20000 AFIX 0 C18 1 0.126900 0.572914 0.659597 11.00000 0.06386 0.06259 = 0.06948 -0.01049 -0.00009 -0.02687 AFIX 43 H18 2 0.041091 0.541806 0.705103 11.00000 -1.20000 AFIX 0 C7 1 0.004842 0.783257 0.854768 11.00000 0.05136 0.04478 = 0.05386 -0.00423 -0.01155 -0.01477 C23 1 -0.308131 0.973689 1.055714 11.00000 0.05148 0.05667 = 0.06149 -0.02805 -0.01209 0.00253 C12 1 0.114247 1.077383 0.602374 11.00000 0.09442 0.05018 = 0.05780 -0.00743 0.00420 -0.02887 C17 1 0.232723 0.644685 0.674855 11.00000 0.04301 0.04469 = 0.05759 -0.00524 -0.00718 -0.00395 C16 1 -0.232536 0.813313 0.679866 11.00000 0.04880 0.07011 = 0.09143 -0.02476 -0.00667 -0.01338 AFIX 137 H16A 2 -0.175980 0.743963 0.659352 11.00000 -1.50000 H16B 2 -0.335392 0.848672 0.651524 11.00000 -1.50000 H16C 2 -0.263045 0.787383 0.744162 11.00000 -1.50000 AFIX 0 C2 1 -0.479325 1.001061 1.188835 11.00000 0.06438 0.12231 = 0.09373 -0.07509 -0.00586 0.01241 AFIX 43 H2A 2 -0.521578 1.048307 1.228395 11.00000 -1.20000 AFIX 0 C6 1 -0.175533 0.888958 0.947469 11.00000 0.04413 0.04642 = 0.05424 -0.00957 -0.00602 -0.00449 C13 1 -0.035837 1.105468 0.565684 11.00000 0.09726 0.05093 = 0.05085 -0.00570 -0.00287 0.00207 AFIX 43 H13 2 -0.062559 1.180798 0.523695 11.00000 -1.20000 AFIX 0 C19 1 0.146900 0.546673 0.577435 11.00000 0.07987 0.07010 = 0.06709 -0.02049 -0.00650 -0.02946 AFIX 43 H19 2 0.076771 0.496089 0.569820 11.00000 -1.20000 AFIX 0 C11 1 0.154162 0.968796 0.668843 11.00000 0.06025 0.05052 = 0.06301 -0.00541 -0.00696 -0.01801 AFIX 43 H11 2 0.254901 0.952819 0.695468 11.00000 -1.20000 AFIX 0 C1 1 -0.369270 1.046414 1.110385 11.00000 0.06895 0.07084 = 0.09814 -0.04855 -0.02339 0.00991 AFIX 43 H1B 2 -0.338908 1.124279 1.096143 11.00000 -1.20000 AFIX 0 C4 1 -0.461994 0.810273 1.153430 11.00000 0.05949 0.08629 = 0.08518 -0.02791 -0.00292 -0.01902 AFIX 43 H4 2 -0.491228 0.732158 1.167194 11.00000 -1.20000 AFIX 0 C3 1 -0.526146 0.884953 1.208074 11.00000 0.06080 0.11569 = 0.10842 -0.04486 -0.00918 -0.00490 AFIX 43 H3 2 -0.603115 0.857402 1.259462 11.00000 -1.20000 AFIX 0 O1S 7 0.072451 0.792351 0.120540 11.00000 0.08538 0.04634 = 0.09273 -0.01920 -0.01903 -0.00326 AFIX 147 H1S 2 0.145246 0.731293 0.121783 11.00000 -1.50000 AFIX 0 C1S 1 -0.004830 0.789930 0.210609 11.00000 0.09440 0.07465 = 0.07020 -0.01726 -0.01336 0.00645 AFIX 137 H1SA 2 -0.088774 0.862041 0.209230 11.00000 -1.50000 H1SB 2 0.083203 0.787713 0.245872 11.00000 -1.50000 H1SC 2 -0.060745 0.718412 0.237124 11.00000 -1.50000 AFIX 0 HKLF 4 REM REM R1 = 0.0640 for 3624 Fo > 4sig(Fo) and 0.0874 for all 4826 data REM 324 parameters refined using 0 restraints END WGHT 0.1044 2.9006 REM Instructions for potential hydrogen bonds EQIV $1 -x+1, -y+1, -z+1 HTAB O1 Br1C_$1 HTAB O1W Br1C EQIV $2 -x+1, -y+1, -z HTAB O1W Br1C_$2 EQIV $3 -x, -y+2, -z+1 HTAB N1 O1S_$3 EQIV $4 -x, -y+1, -z+1 HTAB N2 O1W_$4 EQIV $5 -x+1, -y+2, -z+1 HTAB C21 Cl1_$5 EQIV $6 x, y, z+1 HTAB C8 O1W_$6 HTAB C19 Br1_$4 HTAB C11 O1 HTAB O1S Br1C REM Highest difference peak 0.713, deepest hole -1.292, 1-sigma level 0.129 Q1 1 0.3853 0.5816 0.4283 11.00000 0.05 0.71 Q2 1 0.4413 0.5211 0.3798 11.00000 0.05 0.69 Q3 1 0.2213 0.6380 0.4008 11.00000 0.05 0.69 Q4 1 0.4168 0.4521 0.1569 11.00000 0.05 0.69 Q5 1 0.1768 0.6216 0.4101 11.00000 0.05 0.68 Q6 1 0.1924 0.5244 0.1336 11.00000 0.05 0.64 Q7 1 0.2160 0.5822 0.1789 11.00000 0.05 0.63 Q8 1 0.1596 0.5504 0.3643 11.00000 0.05 0.61 Q9 1 0.3635 0.4766 0.0833 11.00000 0.05 0.59 Q10 1 0.2171 0.6012 0.4849 11.00000 0.05 0.57 ; _shelx_res_checksum 79460 _olex2_submission_special_instructions 'No special instructions were received' 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 Br1C Br 0.31421(10) 0.51653(7) 0.17057(6) 0.0648(3) Uani 1 1 d . . . . . Br1 Br 0.28858(13) 0.56747(10) 0.39475(7) 0.0812(4) Uani 1 1 d . . . . . S1 S 0.0676(3) 0.64462(16) 0.93497(13) 0.0612(5) Uani 1 1 d . . . . . Cl1 Cl 0.2574(5) 1.1838(3) 0.5690(2) 0.1241(12) Uani 1 1 d . . . . . O1 O 0.3637(6) 0.7180(4) 0.7720(4) 0.0606(13) Uani 1 1 d . . . . . H1 H 0.4421 0.6601 0.7827 0.091 Uiso 1 1 calc GR . . . . O1W O 0.4036(10) 0.3751(7) 0.0130(5) 0.090(2) Uani 1 1 d . . . . . H1WA H 0.3749 0.3972 0.0610 0.134 Uiso 1 1 d G . . . . H1WB H 0.5134 0.3608 0.0025 0.134 Uiso 1 1 d G . . . . N4 N 0.0708(7) 0.7765(5) 0.7685(4) 0.0487(13) Uani 1 1 d . . . . . N1 N -0.1965(8) 0.9893(5) 0.9738(4) 0.0586(15) Uani 1 1 d . . . . . H1A H -0.1495 1.0537 0.9453 0.070 Uiso 1 1 calc R . . . . C10 C 0.0387(8) 0.8850(6) 0.6941(5) 0.0491(15) Uani 1 1 d . . . . . N3 N -0.0843(8) 0.8831(5) 0.8667(4) 0.0578(15) Uani 1 1 d . . . . . N2 N -0.2657(7) 0.8068(5) 1.0063(4) 0.0542(14) Uani 1 1 d . . . . . H2 H -0.2712 0.7354 1.0023 0.065 Uiso 1 1 calc R . . . . C20 C 0.2708(10) 0.5951(7) 0.5059(6) 0.0614(18) Uani 1 1 d . . . . . C15 C -0.1120(9) 0.9073(6) 0.6556(5) 0.0509(15) Uani 1 1 d . . . . . C9 C 0.2139(8) 0.6759(6) 0.7626(5) 0.0492(15) Uani 1 1 d . . . . . C14 C -0.1487(11) 1.0196(7) 0.5920(5) 0.0653(19) Uani 1 1 d . . . . . H14 H -0.2511 1.0376 0.5666 0.078 Uiso 1 1 calc R . . . . C5 C -0.3518(9) 0.8571(7) 1.0769(5) 0.0565(17) Uani 1 1 d . . . . . C21 C 0.3736(10) 0.6670(8) 0.5219(6) 0.067(2) Uani 1 1 d . . . . . H21 H 0.4570 0.7007 0.4759 0.080 Uiso 1 1 calc R . . . . C8 C 0.1641(10) 0.5727(6) 0.8477(5) 0.0576(17) Uani 1 1 d . . . . . H8A H 0.2660 0.5148 0.8659 0.069 Uiso 1 1 calc R . . . . H8B H 0.0823 0.5291 0.8360 0.069 Uiso 1 1 calc R . . . . C22 C 0.3565(10) 0.6904(8) 0.6035(6) 0.069(2) Uani 1 1 d . . . . . H22 H 0.4301 0.7384 0.6115 0.083 Uiso 1 1 calc R . . . . C18 C 0.1269(10) 0.5729(7) 0.6596(6) 0.066(2) Uani 1 1 d . . . . . H18 H 0.0411 0.5418 0.7051 0.079 Uiso 1 1 calc R . . . . C7 C 0.0048(9) 0.7833(6) 0.8548(5) 0.0506(15) Uani 1 1 d . . . . . C23 C -0.3081(9) 0.9737(7) 1.0557(5) 0.0548(16) Uani 1 1 d . . . . . C12 C 0.1142(12) 1.0774(7) 0.6024(6) 0.069(2) Uani 1 1 d . . . . . C17 C 0.2327(8) 0.6447(6) 0.6749(5) 0.0509(15) Uani 1 1 d . . . . . C16 C -0.2325(10) 0.8133(8) 0.6799(7) 0.069(2) Uani 1 1 d . . . . . H16A H -0.1760 0.7440 0.6594 0.104 Uiso 1 1 calc GR . . . . H16B H -0.3354 0.8487 0.6515 0.104 Uiso 1 1 calc GR . . . . H16C H -0.2630 0.7874 0.7442 0.104 Uiso 1 1 calc GR . . . . C2 C -0.4793(12) 1.0011(11) 1.1888(7) 0.087(3) Uani 1 1 d . . . . . H2A H -0.5216 1.0483 1.2284 0.105 Uiso 1 1 calc R . . . . C6 C -0.1755(8) 0.8890(6) 0.9475(5) 0.0498(15) Uani 1 1 d . . . . . C13 C -0.0358(12) 1.1055(7) 0.5657(5) 0.071(2) Uani 1 1 d . . . . . H13 H -0.0626 1.1808 0.5237 0.085 Uiso 1 1 calc R . . . . C19 C 0.1469(11) 0.5467(8) 0.5774(6) 0.070(2) Uani 1 1 d . . . . . H19 H 0.0768 0.4961 0.5698 0.084 Uiso 1 1 calc R . . . . C11 C 0.1542(10) 0.9688(6) 0.6688(5) 0.0592(18) Uani 1 1 d . . . . . H11 H 0.2549 0.9528 0.6955 0.071 Uiso 1 1 calc R . . . . C1 C -0.3693(11) 1.0464(8) 1.1104(7) 0.075(2) Uani 1 1 d . . . . . H1B H -0.3389 1.1243 1.0961 0.090 Uiso 1 1 calc R . . . . C4 C -0.4620(11) 0.8103(9) 1.1534(7) 0.076(2) Uani 1 1 d . . . . . H4 H -0.4912 0.7322 1.1672 0.091 Uiso 1 1 calc R . . . . C3 C -0.5261(12) 0.8850(11) 1.2081(8) 0.093(3) Uani 1 1 d . . . . . H3 H -0.6031 0.8574 1.2595 0.112 Uiso 1 1 calc R . . . . O1S O 0.0725(8) 0.7924(5) 0.1205(4) 0.0749(16) Uani 1 1 d . . . . . H1S H 0.1452 0.7313 0.1218 0.112 Uiso 1 1 calc GR . . . . C1S C -0.0048(13) 0.7899(9) 0.2106(6) 0.083(3) Uani 1 1 d . . . . . H1SA H -0.0888 0.8620 0.2092 0.124 Uiso 1 1 calc GR . . . . H1SB H 0.0832 0.7877 0.2459 0.124 Uiso 1 1 calc GR . . . . H1SC H -0.0607 0.7184 0.2371 0.124 Uiso 1 1 calc GR . . . . 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 Br1C 0.0622(5) 0.0534(5) 0.0747(6) -0.0172(4) -0.0054(4) -0.0041(3) Br1 0.0812(7) 0.0891(7) 0.0718(6) -0.0261(5) -0.0159(5) 0.0018(5) S1 0.0726(11) 0.0458(9) 0.0551(10) -0.0027(7) -0.0098(8) -0.0032(8) Cl1 0.159(3) 0.0917(18) 0.118(2) 0.0084(16) -0.007(2) -0.082(2) O1 0.045(2) 0.056(3) 0.081(4) -0.018(3) -0.013(2) -0.007(2) O1W 0.109(5) 0.094(5) 0.082(4) -0.041(4) 0.016(4) -0.055(4) N4 0.046(3) 0.041(3) 0.052(3) -0.005(2) -0.003(2) -0.007(2) N1 0.063(4) 0.040(3) 0.074(4) -0.014(3) -0.018(3) -0.003(2) C10 0.046(3) 0.039(3) 0.056(4) -0.007(3) -0.002(3) -0.007(2) N3 0.057(3) 0.040(3) 0.070(4) -0.004(3) -0.013(3) -0.008(2) N2 0.059(3) 0.049(3) 0.057(3) -0.015(3) -0.007(3) -0.014(2) C20 0.057(4) 0.055(4) 0.070(5) -0.019(3) -0.013(4) 0.004(3) C15 0.055(4) 0.047(3) 0.051(4) -0.017(3) -0.007(3) -0.002(3) C9 0.043(3) 0.039(3) 0.060(4) -0.008(3) -0.009(3) -0.003(2) C14 0.071(5) 0.056(4) 0.062(5) -0.011(3) -0.016(4) 0.006(4) C5 0.050(4) 0.059(4) 0.064(4) -0.021(3) -0.013(3) -0.007(3) C21 0.058(4) 0.084(5) 0.062(5) -0.024(4) -0.004(4) -0.016(4) C8 0.062(4) 0.044(3) 0.059(4) -0.006(3) -0.008(3) -0.004(3) C22 0.050(4) 0.074(5) 0.081(6) -0.010(4) -0.011(4) -0.023(4) C18 0.064(4) 0.063(4) 0.069(5) -0.010(4) 0.000(4) -0.027(4) C7 0.051(3) 0.045(3) 0.054(4) -0.004(3) -0.012(3) -0.015(3) C23 0.051(4) 0.057(4) 0.061(4) -0.028(3) -0.012(3) 0.003(3) C12 0.094(6) 0.050(4) 0.058(5) -0.007(3) 0.004(4) -0.029(4) C17 0.043(3) 0.045(3) 0.058(4) -0.005(3) -0.007(3) -0.004(3) C16 0.049(4) 0.070(5) 0.091(6) -0.025(4) -0.007(4) -0.013(3) C2 0.064(5) 0.122(8) 0.094(7) -0.075(7) -0.006(5) 0.012(5) C6 0.044(3) 0.046(3) 0.054(4) -0.010(3) -0.006(3) -0.004(3) C13 0.097(6) 0.051(4) 0.051(4) -0.006(3) -0.003(4) 0.002(4) C19 0.080(5) 0.070(5) 0.067(5) -0.020(4) -0.006(4) -0.029(4) C11 0.060(4) 0.051(4) 0.063(5) -0.005(3) -0.007(3) -0.018(3) C1 0.069(5) 0.071(5) 0.098(7) -0.049(5) -0.023(5) 0.010(4) C4 0.059(5) 0.086(6) 0.085(6) -0.028(5) -0.003(4) -0.019(4) C3 0.061(5) 0.116(8) 0.108(8) -0.045(7) -0.009(5) -0.005(5) O1S 0.085(4) 0.046(3) 0.093(4) -0.019(3) -0.019(3) -0.003(3) C1S 0.094(7) 0.075(5) 0.070(6) -0.017(4) -0.013(5) 0.006(5) 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' N N 0.0311 0.0180 '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' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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' 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 C7 S1 C8 91.5(3) . . ? C9 O1 H1 109.5 . . ? H1WA O1W H1WB 109.5 . . ? C10 N4 C9 123.1(5) . . ? C7 N4 C10 117.9(5) . . ? C7 N4 C9 115.6(5) . . ? C23 N1 H1A 125.4 . . ? C6 N1 H1A 125.4 . . ? C6 N1 C23 109.2(6) . . ? C15 C10 N4 119.5(6) . . ? C15 C10 C11 122.0(6) . . ? C11 C10 N4 118.3(6) . . ? C7 N3 C6 122.3(6) . . ? C5 N2 H2 126.0 . . ? C6 N2 H2 126.0 . . ? C6 N2 C5 108.1(6) . . ? C21 C20 Br1 122.1(6) . . ? C21 C20 C19 116.7(8) . . ? C19 C20 Br1 121.2(6) . . ? C10 C15 C14 117.8(7) . . ? C10 C15 C16 121.8(6) . . ? C14 C15 C16 120.4(7) . . ? O1 C9 N4 105.2(5) . . ? O1 C9 C8 109.9(6) . . ? O1 C9 C17 111.8(6) . . ? N4 C9 C8 102.2(5) . . ? N4 C9 C17 112.0(5) . . ? C17 C9 C8 114.9(6) . . ? C15 C14 H14 119.3 . . ? C13 C14 C15 121.4(7) . . ? C13 C14 H14 119.3 . . ? C23 C5 N2 106.6(6) . . ? C4 C5 N2 131.3(7) . . ? C4 C5 C23 122.1(8) . . ? C20 C21 H21 119.0 . . ? C22 C21 C20 121.9(8) . . ? C22 C21 H21 119.0 . . ? S1 C8 H8A 110.4 . . ? S1 C8 H8B 110.4 . . ? C9 C8 S1 106.8(5) . . ? C9 C8 H8A 110.4 . . ? C9 C8 H8B 110.4 . . ? H8A C8 H8B 108.6 . . ? C21 C22 H22 118.9 . . ? C21 C22 C17 122.2(7) . . ? C17 C22 H22 118.9 . . ? C17 C18 H18 119.4 . . ? C17 C18 C19 121.2(7) . . ? C19 C18 H18 119.4 . . ? N4 C7 S1 110.5(5) . . ? N3 C7 S1 129.5(6) . . ? N3 C7 N4 120.0(6) . . ? C5 C23 N1 105.8(6) . . ? C1 C23 N1 132.9(8) . . ? C1 C23 C5 121.3(8) . . ? C13 C12 Cl1 119.0(6) . . ? C13 C12 C11 122.3(7) . . ? C11 C12 Cl1 118.6(7) . . ? C22 C17 C9 120.7(7) . . ? C18 C17 C9 122.7(6) . . ? C18 C17 C22 116.6(8) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C1 C2 H2A 119.9 . . ? C1 C2 C3 120.1(9) . . ? C3 C2 H2A 119.9 . . ? N1 C6 N3 121.3(6) . . ? N1 C6 N2 110.4(7) . . ? N2 C6 N3 128.1(6) . . ? C14 C13 H13 120.6 . . ? C12 C13 C14 118.7(7) . . ? C12 C13 H13 120.6 . . ? C20 C19 H19 119.3 . . ? C18 C19 C20 121.3(7) . . ? C18 C19 H19 119.3 . . ? C10 C11 C12 117.7(7) . . ? C10 C11 H11 121.2 . . ? C12 C11 H11 121.2 . . ? C23 C1 C2 118.0(9) . . ? C23 C1 H1B 121.0 . . ? C2 C1 H1B 121.0 . . ? C5 C4 H4 121.8 . . ? C3 C4 C5 116.5(9) . . ? C3 C4 H4 121.8 . . ? C2 C3 H3 119.0 . . ? C4 C3 C2 121.9(10) . . ? C4 C3 H3 119.0 . . ? C1S O1S H1S 109.5 . . ? O1S C1S H1SA 109.5 . . ? O1S C1S H1SB 109.5 . . ? O1S C1S H1SC 109.5 . . ? H1SA C1S H1SB 109.5 . . ? H1SA C1S H1SC 109.5 . . ? H1SB C1S H1SC 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 Br1 C20 1.848(8) . ? S1 C8 1.802(8) . ? S1 C7 1.755(6) . ? Cl1 C12 1.738(8) . ? O1 H1 0.8200 . ? O1 C9 1.419(8) . ? O1W H1WA 0.8502 . ? O1W H1WB 0.8503 . ? N4 C10 1.444(8) . ? N4 C9 1.474(8) . ? N4 C7 1.384(9) . ? N1 H1A 0.8600 . ? N1 C23 1.407(10) . ? N1 C6 1.324(9) . ? C10 C15 1.382(9) . ? C10 C11 1.386(9) . ? N3 C7 1.283(9) . ? N3 C6 1.358(9) . ? N2 H2 0.8600 . ? N2 C5 1.420(10) . ? N2 C6 1.325(8) . ? C20 C21 1.378(11) . ? C20 C19 1.404(12) . ? C15 C14 1.389(10) . ? C15 C16 1.506(10) . ? C9 C8 1.543(9) . ? C9 C17 1.507(10) . ? C14 H14 0.9300 . ? C14 C13 1.388(12) . ? C5 C23 1.386(10) . ? C5 C4 1.380(12) . ? C21 H21 0.9300 . ? C21 C22 1.371(12) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C22 H22 0.9300 . ? C22 C17 1.393(10) . ? C18 H18 0.9300 . ? C18 C17 1.389(10) . ? C18 C19 1.392(12) . ? C23 C1 1.352(11) . ? C12 C13 1.357(13) . ? C12 C11 1.388(10) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C2 H2A 0.9300 . ? C2 C1 1.395(14) . ? C2 C3 1.396(15) . ? C13 H13 0.9300 . ? C19 H19 0.9300 . ? C11 H11 0.9300 . ? C1 H1B 0.9300 . ? C4 H4 0.9300 . ? C4 C3 1.372(14) . ? C3 H3 0.9300 . ? O1S H1S 0.8200 . ? O1S C1S 1.432(11) . ? C1S H1SA 0.9600 . ? C1S H1SB 0.9600 . ? C1S H1SC 0.9600 . ? 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 Br1 C20 C21 C22 177.9(6) . . . . ? Br1 C20 C19 C18 -176.4(6) . . . . ? Cl1 C12 C13 C14 179.4(7) . . . . ? Cl1 C12 C11 C10 -179.7(6) . . . . ? O1 C9 C8 S1 75.0(6) . . . . ? O1 C9 C17 C22 -19.1(8) . . . . ? O1 C9 C17 C18 162.8(6) . . . . ? N4 C10 C15 C14 172.2(7) . . . . ? N4 C10 C15 C16 -8.8(10) . . . . ? N4 C10 C11 C12 -174.8(7) . . . . ? N4 C9 C8 S1 -36.3(6) . . . . ? N4 C9 C17 C22 98.7(7) . . . . ? N4 C9 C17 C18 -79.5(8) . . . . ? N1 C23 C1 C2 -179.5(8) . . . . ? C10 N4 C9 O1 78.8(7) . . . . ? C10 N4 C9 C8 -166.3(6) . . . . ? C10 N4 C9 C17 -42.8(8) . . . . ? C10 N4 C7 S1 -177.0(4) . . . . ? C10 N4 C7 N3 1.2(9) . . . . ? C10 C15 C14 C13 1.9(12) . . . . ? N2 C5 C23 N1 -0.5(7) . . . . ? N2 C5 C23 C1 -179.7(7) . . . . ? N2 C5 C4 C3 -178.9(8) . . . . ? C20 C21 C22 C17 -1.0(13) . . . . ? C15 C10 C11 C12 -0.3(12) . . . . ? C15 C14 C13 C12 0.9(13) . . . . ? C9 N4 C10 C15 114.6(7) . . . . ? C9 N4 C10 C11 -70.7(9) . . . . ? C9 N4 C7 S1 -17.0(7) . . . . ? C9 N4 C7 N3 161.2(6) . . . . ? C5 N2 C6 N1 -0.4(8) . . . . ? C5 N2 C6 N3 -174.8(6) . . . . ? C5 C23 C1 C2 -0.5(12) . . . . ? C5 C4 C3 C2 -1.6(14) . . . . ? C21 C20 C19 C18 1.5(12) . . . . ? C21 C22 C17 C9 -177.9(7) . . . . ? C21 C22 C17 C18 0.4(11) . . . . ? C8 S1 C7 N4 -6.1(5) . . . . ? C8 S1 C7 N3 175.9(7) . . . . ? C8 C9 C17 C22 -145.3(7) . . . . ? C8 C9 C17 C18 36.5(9) . . . . ? C7 S1 C8 C9 25.5(5) . . . . ? C7 N4 C10 C15 -87.0(8) . . . . ? C7 N4 C10 C11 87.7(8) . . . . ? C7 N4 C9 O1 -80.0(6) . . . . ? C7 N4 C9 C8 34.8(7) . . . . ? C7 N4 C9 C17 158.4(5) . . . . ? C7 N3 C6 N1 147.4(7) . . . . ? C7 N3 C6 N2 -38.8(11) . . . . ? C23 N1 C6 N3 174.9(6) . . . . ? C23 N1 C6 N2 0.0(8) . . . . ? C23 C5 C4 C3 -0.3(12) . . . . ? C17 C9 C8 S1 -157.9(5) . . . . ? C17 C18 C19 C20 -2.2(13) . . . . ? C16 C15 C14 C13 -177.1(8) . . . . ? C6 N1 C23 C5 0.3(8) . . . . ? C6 N1 C23 C1 179.4(8) . . . . ? C6 N3 C7 S1 -13.3(10) . . . . ? C6 N3 C7 N4 168.8(6) . . . . ? C6 N2 C5 C23 0.6(8) . . . . ? C6 N2 C5 C4 179.3(8) . . . . ? C13 C12 C11 C10 3.3(13) . . . . ? C19 C20 C21 C22 0.1(12) . . . . ? C19 C18 C17 C9 179.4(7) . . . . ? C19 C18 C17 C22 1.2(11) . . . . ? C11 C10 C15 C14 -2.2(11) . . . . ? C11 C10 C15 C16 176.8(8) . . . . ? C11 C12 C13 C14 -3.6(13) . . . . ? C1 C2 C3 C4 2.4(15) . . . . ? C4 C5 C23 N1 -179.4(7) . . . . ? C4 C5 C23 C1 1.4(12) . . . . ? C3 C2 C1 C23 -1.3(14) . . . . ?