#------------------------------------------------------------------------------ #$Date: 2023-11-18 04:11:38 +0200 (Sat, 18 Nov 2023) $ #$Revision: 287683 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247752.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_7247752 loop_ _publ_author_name 'Qadri, Tahir' 'Aziz, Mubashir' 'Channar, Pervaiz Ali' 'Ejaz, Syeda Abida' 'Hussain, Mumtaz' 'Attaullah, Hafiz Muhammad' 'Ujan, Rabail' 'Hussain, Zahid' 'Zehra, Tasneem' 'Saeed, Aamer' 'Shah, M. R.' 'Ogaly, Hanan A.' 'Al-Zahrani, Fatimah A. M.' _publ_section_title ; Synthesis, biological evaluation and in silico investigations of benzotriazole derivatives as potential inhibitors of NIMA related kinase ; _journal_issue 48 _journal_name_full 'RSC Advances' _journal_page_first 33826 _journal_page_last 33843 _journal_paper_doi 10.1039/D3RA06149C _journal_volume 13 _journal_year 2023 _chemical_formula_moiety 'C16 H12 Cl2 N2 O2 S' _chemical_formula_sum 'C16 H12 Cl2 N2 O2 S' _chemical_formula_weight 367.24 _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 geom _atom_sites_solution_primary dual _audit_block_doi 10.5517/ccdc.csd.cc2b4x6m _audit_creation_date 2019-01-16 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2022-02-05 deposited with the CCDC. 2023-11-07 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 111.168(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.6684(8) _cell_length_b 9.1256(4) _cell_length_c 14.0839(8) _cell_measurement_reflns_used 2861 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 71.4640 _cell_measurement_theta_min 3.8380 _cell_volume 1638.18(17) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 173(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0416 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.973 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -60.00 -34.00 1.00 1.00 -- -33.50 77.00 120.00 26 2 \w 2.00 34.00 1.00 1.00 -- -33.50 77.00 120.00 32 3 \w 65.00 101.00 1.00 1.00 -- 35.36 178.00 -60.00 36 4 \w 109.00 147.00 1.00 1.21 -- 108.00 111.00 -30.00 38 5 \w 93.00 175.00 1.00 1.21 -- 108.00 61.00 30.00 82 6 \w 102.00 153.00 1.00 1.21 -- 108.00 0.00 150.00 51 7 \w 81.00 173.00 1.00 1.21 -- 108.00 77.00 150.00 92 8 \w 77.00 108.00 1.00 1.21 -- 108.00 -94.00 60.00 31 9 \w 73.00 99.00 1.00 1.21 -- 108.00-111.00 -60.00 26 10 \w 56.00 101.00 1.00 1.21 -- 108.00 -61.00-120.00 45 11 \w 40.00 88.00 1.00 1.21 -- 108.00 -94.00-120.00 48 12 \w 39.00 64.00 1.00 1.21 -- 108.00-111.00 -60.00 25 13 \w 42.00 133.00 1.00 1.21 -- 108.00 -77.00 30.00 91 14 \w 74.00 100.00 1.00 1.00 -- 35.36-178.00-150.00 26 15 \w -97.00 -47.00 1.00 1.00 -- -33.50-178.00 0.00 50 16 \w -101.00 -9.00 1.00 1.00 -- -33.50 -77.00 0.00 92 17 \w -104.00 -39.00 1.00 1.00 -- -33.50-178.00-180.00 65 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Rigaku Oxford Diffraction' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.1068066000 _diffrn_orient_matrix_UB_12 0.0017055000 _diffrn_orient_matrix_UB_13 -0.0139331000 _diffrn_orient_matrix_UB_21 -0.0129609000 _diffrn_orient_matrix_UB_22 -0.1634538000 _diffrn_orient_matrix_UB_23 -0.0290206000 _diffrn_orient_matrix_UB_31 -0.0551510000 _diffrn_orient_matrix_UB_32 0.0417738000 _diffrn_orient_matrix_UB_33 -0.1127869000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_unetI/netI 0.0462 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.973 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 6234 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.973 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 71.563 _diffrn_reflns_theta_min 3.863 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 4.847 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.48848 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.489 _exptl_crystal_description prism _exptl_crystal_F_000 752 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.561 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.084 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 209 _refine_ls_number_reflns 3112 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0427 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+0.0672P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1159 _refine_ls_wR_factor_ref 0.1215 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2743 _reflns_number_total 3112 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ra06149c2.cif _cod_data_source_block as-ak-tu-2-4-cl _cod_database_code 7247752 _shelx_shelxl_version_number 2018/1 _chemical_oxdiff_formula 'C16 H12 N2 S1 O2 Cl2' _chemical_oxdiff_usercomment 'Aamer Saeed's AS-AK-TU-2-4-Cl' _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 0.594 _shelx_estimated_absorpt_t_min 0.389 _reflns_odcompleteness_completeness 99.94 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 68.13 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: N1(H1), N2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C13(H13), C15(H15), C16(H16) 2.b Idealised Me refined as rotating group: C10(H10A,H10B,H10C) ; _shelx_res_file ; TITL as-ak-tu-2-4-cl_a.res in P2(1)/n as-ak-tu-2-4-cl.res created by SHELXL-2018/1 at 15:56:12 on 16-Jan-2019 REM Old TITL as-ak-tu-2-4-cl_a.res in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.132, Rweak 0.088, Alpha 0.023, Orientation as input REM Formula found by SHELXT: C16 Cl3 N2 O2 CELL 1.54184 13.6684 9.1256 14.0839 90 111.168 90 ZERR 4 0.0008 0.0004 0.0008 0 0.007 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Cl N O S UNIT 64 48 8 8 8 4 EQIV $1 1-X,1-Y,1-Z EQIV $2 1.5-X,0.5+Y,0.5-Z EQIV $3 -0.5+X,1.5-Y,-0.5+Z L.S. 50 PLAN 20 SIZE 0.24 0.14 0.12 TEMP -100(2) HTAB N1 S1_$1 HTAB N2 O1 HTAB C7 O1_$2 HTAB C8 O2_$3 BOND $H list 4 ABIN fmap 2 acta OMIT 12 1 6 OMIT 12 3 6 OMIT 11 0 7 OMIT 12 0 6 OMIT -1 0 3 REM REM REM WGHT 0.075000 0.067200 FVAR 0.57639 CL1 3 0.469989 0.177867 0.289791 11.00000 0.02297 0.01739 = 0.02582 0.00015 -0.00247 0.00546 CL2 3 0.072443 0.326439 0.072284 11.00000 0.01434 0.03012 = 0.04587 -0.00038 -0.00579 -0.00536 S1 6 0.655919 0.590459 0.565117 11.00000 0.01457 0.02258 = 0.01320 -0.00531 0.00164 -0.00258 O1 5 0.583093 0.519393 0.224960 11.00000 0.01725 0.03994 = 0.01703 -0.00274 0.00397 -0.00756 O2 5 1.197426 0.672555 0.706792 11.00000 0.02061 0.04507 = 0.02834 0.00425 -0.01041 -0.00230 N1 4 0.552250 0.516560 0.374458 11.00000 0.01186 0.02483 = 0.01485 -0.00577 0.00281 -0.00657 AFIX 43 H1 2 0.503142 0.496470 0.399193 11.00000 -1.20000 AFIX 0 N2 4 0.724577 0.586666 0.409133 11.00000 0.01183 0.02545 = 0.01181 -0.00267 -0.00004 -0.00336 AFIX 43 H2 2 0.708711 0.574660 0.343262 11.00000 -1.20000 AFIX 0 C1 1 0.524707 0.497691 0.271498 11.00000 0.01708 0.01398 = 0.01375 -0.00246 0.00211 -0.00164 C2 1 0.647919 0.563425 0.445017 11.00000 0.01105 0.01304 = 0.01346 -0.00137 -0.00163 -0.00058 C3 1 0.829379 0.628929 0.466932 11.00000 0.01212 0.01872 = 0.01432 -0.00345 0.00115 -0.00019 C4 1 0.886649 0.559260 0.557757 11.00000 0.01952 0.01727 = 0.01829 0.00317 0.00459 0.00016 AFIX 43 H4 2 0.854999 0.485258 0.584484 11.00000 -1.20000 AFIX 0 C5 1 0.990029 0.598533 0.608872 11.00000 0.01604 0.02163 = 0.01539 0.00315 0.00011 0.00381 AFIX 43 H5 2 1.029231 0.550923 0.670979 11.00000 -1.20000 AFIX 0 C6 1 1.037639 0.706617 0.570895 11.00000 0.01254 0.02061 = 0.01484 -0.00388 0.00170 0.00016 C7 1 0.979534 0.774764 0.479601 11.00000 0.01747 0.02174 = 0.01852 0.00194 0.00388 -0.00327 AFIX 43 H7 2 1.011332 0.848259 0.452613 11.00000 -1.20000 AFIX 0 C8 1 0.875761 0.736628 0.427575 11.00000 0.01453 0.02416 = 0.01321 0.00399 -0.00156 -0.00091 AFIX 43 H8 2 0.836546 0.783882 0.365325 11.00000 -1.20000 AFIX 0 C9 1 1.151526 0.738359 0.628425 11.00000 0.01609 0.02718 = 0.01817 -0.00702 0.00046 0.00067 C10 1 1.206396 0.848247 0.587637 11.00000 0.01560 0.05295 = 0.03218 -0.00221 0.00560 -0.01150 AFIX 137 H10A 2 1.275923 0.868321 0.638711 11.00000 -1.50000 H10B 2 1.165400 0.939061 0.571595 11.00000 -1.50000 H10C 2 1.214043 0.809812 0.525713 11.00000 -1.50000 AFIX 0 C11 1 0.412163 0.453094 0.219570 11.00000 0.01478 0.01702 = 0.01147 -0.00444 0.00169 -0.00332 C12 1 0.379193 0.309636 0.224646 11.00000 0.01790 0.01370 = 0.01083 -0.00201 0.00061 0.00182 C13 1 0.275206 0.269743 0.179311 11.00000 0.02163 0.01346 = 0.01526 -0.00320 0.00385 -0.00442 AFIX 43 H13 2 0.253516 0.171682 0.183000 11.00000 -1.20000 AFIX 0 C14 1 0.203308 0.376279 0.128321 11.00000 0.01510 0.02279 = 0.01795 -0.00284 0.00109 -0.00257 C15 1 0.233231 0.518929 0.120094 11.00000 0.01756 0.01806 = 0.02041 -0.00025 -0.00320 0.00180 AFIX 43 H15 2 0.182819 0.590216 0.084130 11.00000 -1.20000 AFIX 0 C16 1 0.338303 0.555899 0.165385 11.00000 0.02373 0.01519 = 0.01870 0.00073 0.00287 -0.00341 AFIX 43 H16 2 0.360084 0.653155 0.159226 11.00000 -1.20000 AFIX 0 HKLF 4 REM as-ak-tu-2-4-cl_a.res in P2(1)/n REM R1 = 0.0427 for 2743 Fo > 4sig(Fo) and 0.0478 for all 3112 data REM 209 parameters refined using 0 restraints END WGHT 0.0756 0.0649 REM Highest difference peak 0.561, deepest hole -0.363, 1-sigma level 0.084 Q1 1 0.6473 0.5818 0.4992 11.00000 0.05 0.56 Q2 1 0.0778 0.3431 0.1371 11.00000 0.05 0.44 Q3 1 0.8625 0.5808 0.5042 11.00000 0.05 0.36 Q4 1 0.6634 0.5767 0.6390 11.00000 0.05 0.33 Q5 1 0.4719 0.1817 0.2272 11.00000 0.05 0.32 Q6 1 0.5957 0.5780 0.6057 11.00000 0.05 0.31 Q7 1 0.3983 0.3949 0.1940 11.00000 0.05 0.30 Q8 1 0.0517 0.4135 0.0015 11.00000 0.05 0.30 Q9 1 0.4211 0.2570 0.2459 11.00000 0.05 0.29 Q10 1 0.4950 0.2550 0.3593 11.00000 0.05 0.28 Q11 1 0.0992 0.3418 0.0006 11.00000 0.05 0.27 Q12 1 0.0982 0.2437 0.1346 11.00000 0.05 0.27 Q13 1 0.0851 0.5422 0.0484 11.00000 0.05 0.26 Q14 1 1.0338 0.8124 0.4109 11.00000 0.05 0.26 Q15 1 0.9213 0.7868 0.4726 11.00000 0.05 0.25 Q16 1 1.1783 0.6946 0.7703 11.00000 0.05 0.24 Q17 1 0.2830 0.5392 0.1631 11.00000 0.05 0.24 Q18 1 0.5538 0.3658 0.4169 11.00000 0.05 0.24 Q19 1 0.7978 0.4092 0.4903 11.00000 0.05 0.24 Q20 1 0.4953 0.3695 0.4605 11.00000 0.05 0.24 ; _shelx_res_checksum 56875 _shelx_fab_file ; -16 0 2 -0.0713 -0.0269 -16 0 4 0.0498 0.0727 -16 0 6 0.1322 -0.0456 -16 0 8 -0.1132 0.0281 -16 0 10 0.1214 0.0140 -16 1 2 0.0542 0.1387 -16 1 3 -0.0406 -0.0108 -16 1 4 -0.0005 0.0517 -16 1 5 -0.1057 0.0606 -16 1 6 -0.0135 -0.0135 -16 1 7 -0.0479 0.0424 -16 1 8 -0.0085 -0.0653 -16 1 9 0.1276 -0.0635 -16 1 10 0.1015 -0.0888 -16 2 2 -0.0307 -0.0347 -16 2 3 -0.0165 -0.0995 -16 2 4 0.1005 -0.0871 -16 2 5 0.0130 -0.0187 -16 2 6 0.0854 -0.1076 -16 2 7 0.1472 -0.0073 -16 2 8 -0.0583 0.0262 -16 2 9 -0.0518 0.0651 -16 3 4 -0.0718 0.0532 -16 3 5 -0.0343 0.1389 -16 3 6 -0.1248 0.0637 -16 3 7 0.0151 0.0549 -16 3 8 -0.2058 0.0226 -15 0 -1 0.2351 0.0772 -15 0 1 -0.1344 -0.1189 -15 0 3 0.0652 0.0165 -15 0 5 -0.0012 0.0240 -15 0 7 0.0858 -0.0322 -15 0 9 -0.2164 0.0180 -15 0 11 0.2523 -0.0005 -15 1 -1 -0.1285 -0.0576 -15 1 0 0.0046 -0.0195 -15 1 1 0.0920 0.0510 -15 1 2 0.0274 0.0427 -15 1 3 0.0246 0.1270 -15 1 4 -0.0196 -0.0187 -15 1 5 -0.0009 0.0745 -15 1 6 -0.1053 0.0837 -15 1 7 -0.0328 0.0390 -15 1 8 0.0354 0.0320 -15 1 9 0.0595 -0.0405 -15 1 10 0.1006 -0.0366 -15 1 11 0.1260 -0.0546 -15 1 12 -0.2215 -0.0011 -15 2 -1 0.0568 0.0833 -15 2 0 -0.0049 0.0624 -15 2 1 -0.0396 0.0365 -15 2 2 -0.2342 -0.0704 -15 2 3 -0.0200 0.0142 -15 2 4 0.0136 -0.0760 -15 2 5 0.0656 -0.0845 -15 2 6 -0.0534 -0.0562 -15 2 7 0.1135 -0.1080 -15 2 8 0.1702 -0.0366 -15 2 9 -0.0998 0.0153 -15 2 10 -0.1396 0.0425 -15 2 11 -0.0729 0.0452 -15 3 0 -0.1203 -0.0655 -15 3 1 0.2596 -0.0315 -15 3 2 0.1203 -0.0698 -15 3 3 0.1819 0.0045 -15 3 4 -0.0146 0.0198 -15 3 5 0.0454 0.0482 -15 3 6 -0.0112 0.1317 -15 3 7 -0.1151 0.0769 -15 3 8 0.0317 0.0539 -15 3 9 -0.2284 0.0417 -15 3 10 0.0333 -0.0518 -15 4 2 -0.3115 0.0658 -15 4 3 -0.1435 0.0769 -15 4 4 -0.0676 0.0113 -15 4 5 -0.0427 -0.0366 -15 4 6 0.0680 -0.0625 -15 4 7 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-0.0601 3 3 12 0.0779 0.0016 3 3 13 -0.0874 -0.0664 3 3 14 -0.2202 0.0303 3 4 3 0.3479 0.0064 3 4 4 0.1646 -0.0307 3 4 5 -0.1270 -0.0406 3 4 6 0.1327 -0.0187 3 4 7 -0.1802 -0.0165 3 4 8 0.0481 0.0249 3 4 9 -0.0139 -0.0059 3 4 10 -0.0757 0.0292 3 4 11 -0.1599 -0.0021 3 4 12 -0.1206 0.0666 3 4 13 0.0958 0.0116 3 5 3 -0.4333 -0.0418 3 5 4 -0.1268 -0.0184 3 5 5 0.0031 0.0343 3 5 6 0.2319 0.0472 3 5 7 0.0301 -0.0029 3 5 8 -0.0724 0.0156 3 5 9 0.0068 -0.0330 3 5 10 -0.0122 -0.0031 3 5 11 0.1274 -0.0442 3 5 12 -0.0184 -0.0421 3 6 3 0.3703 0.0411 3 6 4 0.1427 0.0122 3 6 5 -0.0014 0.0050 3 6 6 -0.2512 -0.0139 3 6 7 -0.1155 -0.0427 3 6 8 -0.1291 0.0227 3 6 9 0.0860 -0.0003 3 6 10 -0.0330 0.0214 3 6 11 0.1270 0.0383 3 7 3 -0.0497 -0.0199 3 7 4 -0.4528 -0.0239 3 7 5 0.0700 0.0086 3 7 6 0.0634 0.0329 3 7 7 0.2718 -0.0157 3 7 8 0.1016 0.0130 3 7 9 0.1115 -0.0121 3 7 10 -0.0877 -0.0234 3 8 3 0.3336 0.0256 3 8 4 -0.0128 0.0179 3 8 5 0.2685 -0.0334 3 8 6 -0.0151 -0.0090 3 8 7 -0.1037 -0.0336 3 8 8 -0.1375 0.0063 3 8 9 -0.0638 0.0327 3 9 3 0.2217 -0.1133 3 9 4 -0.2104 -0.0202 3 9 5 -0.1317 -0.0139 3 9 6 -0.0599 0.0441 3 9 7 -0.0549 0.0403 3 10 3 0.0499 0.0015 3 10 4 -0.0168 0.0986 3 10 5 0.0054 0.0493 4 0 4 -0.0374 0.1100 4 0 6 0.0989 0.0646 4 0 8 0.2411 0.0387 4 0 10 -0.1776 0.0668 4 0 12 0.1168 0.0641 4 0 14 -0.0875 0.0511 4 1 4 -0.0193 0.0819 4 1 5 -0.0188 -0.1001 4 1 6 0.3415 0.0187 4 1 7 -0.2423 -0.0070 4 1 8 -0.0402 0.0271 4 1 9 0.0944 -0.0544 4 1 10 0.0528 0.0284 4 1 11 0.0581 -0.0893 4 1 12 -0.0122 0.0114 4 1 13 -0.0241 -0.0324 4 1 14 -0.1345 -0.0380 4 2 4 0.3679 0.0393 4 2 5 -0.2784 -0.0521 4 2 6 0.1676 0.0168 4 2 7 -0.1368 -0.0192 4 2 8 -0.0734 0.0040 4 2 9 0.0963 -0.0611 4 2 10 -0.1421 0.0584 4 2 11 -0.1647 -0.0089 4 2 12 -0.1409 0.0504 4 2 13 0.1749 0.0561 4 3 4 0.0419 0.0773 4 3 5 -0.2966 0.0072 4 3 6 0.1450 0.0300 4 3 7 0.1315 0.0009 4 3 8 -0.1904 0.0315 4 3 9 0.0799 -0.0136 4 3 10 0.0654 0.0443 4 3 11 0.2610 -0.0260 4 3 12 0.0416 -0.0584 4 3 13 0.1334 -0.0030 4 4 4 0.3699 0.0233 4 4 5 -0.0585 -0.0455 4 4 6 -0.1713 -0.0210 4 4 7 0.1313 -0.0209 4 4 8 -0.1296 0.0054 4 4 9 0.1341 -0.0152 4 4 10 -0.0869 0.0062 4 4 11 0.0042 0.0204 4 4 12 -0.2772 0.0025 4 4 13 -0.1578 0.0760 4 5 4 -0.2736 -0.0113 4 5 5 0.0014 -0.0164 4 5 6 0.0048 0.0384 4 5 7 0.3295 0.0283 4 5 8 -0.0476 0.0008 4 5 9 0.0521 -0.0085 4 5 10 -0.1539 -0.0225 4 5 11 0.0808 0.0048 4 5 12 0.1203 -0.0590 4 6 4 0.3597 0.0295 4 6 5 0.2324 -0.0240 4 6 6 -0.1582 -0.0154 4 6 7 -0.1102 -0.0198 4 6 8 -0.2506 -0.0259 4 6 9 -0.0073 0.0233 4 6 10 -0.0332 -0.0045 4 6 11 0.0024 0.0384 4 7 4 -0.2862 0.0294 4 7 5 -0.3529 0.0105 4 7 6 -0.1338 0.0357 4 7 7 0.1115 0.0489 4 7 8 0.1218 -0.0083 4 7 9 0.1606 0.0205 4 7 10 0.1046 -0.0218 4 8 4 0.2903 0.0123 4 8 5 0.1909 -0.0327 4 8 6 0.2374 -0.0711 4 8 7 0.1031 -0.0215 4 8 8 -0.0251 -0.0469 4 8 9 -0.0832 0.0062 4 9 4 0.1189 -0.0804 4 9 5 -0.1545 0.0229 4 9 6 -0.1356 0.0194 4 10 4 0.0012 0.0203 5 0 5 -0.3946 -0.0048 5 0 7 0.2774 -0.0420 5 0 9 0.0737 0.0357 5 0 11 -0.1783 0.0731 5 0 13 0.0867 0.0382 5 1 5 -0.0127 0.0498 5 1 6 -0.0052 0.0126 5 1 7 0.2967 0.0329 5 1 8 -0.2895 0.0416 5 1 9 -0.1119 0.0462 5 1 10 0.1764 -0.0712 5 1 11 0.1647 0.0343 5 1 12 0.0218 -0.0841 5 1 13 -0.0266 0.0178 5 2 5 0.2447 0.0114 5 2 6 -0.4017 -0.0314 5 2 7 0.2323 -0.0291 5 2 8 0.0166 -0.0526 5 2 9 0.0071 -0.0062 5 2 10 -0.0243 -0.0805 5 2 11 -0.1091 0.0722 5 2 12 -0.2059 -0.0071 5 2 13 -0.1561 0.0420 5 3 5 0.2030 0.0414 5 3 6 -0.3238 0.0034 5 3 7 0.1664 0.0216 5 3 8 -0.0005 0.0088 5 3 9 -0.1546 0.0601 5 3 10 -0.0684 -0.0198 5 3 11 0.1408 0.0600 5 3 12 0.2884 -0.0394 5 4 5 0.4370 0.0221 5 4 6 -0.2053 -0.0361 5 4 7 -0.0813 -0.0169 5 4 8 0.0673 -0.0166 5 4 9 0.0510 0.0221 5 4 10 0.1173 -0.0487 5 4 11 -0.0947 0.0167 5 4 12 0.0144 0.0102 5 5 5 -0.0962 0.0202 5 5 6 -0.0770 0.0099 5 5 7 0.0356 0.0399 5 5 8 0.2012 0.0144 5 5 9 -0.0711 0.0206 5 5 10 0.0616 -0.0272 5 5 11 -0.2367 -0.0054 5 6 5 0.4503 -0.0006 5 6 6 0.2518 -0.0540 5 6 7 -0.0974 -0.0414 5 6 8 0.0121 -0.0454 5 6 9 -0.2550 -0.0118 5 6 10 0.1235 0.0114 5 7 5 -0.3513 0.0632 5 7 6 -0.2851 0.0439 5 7 7 -0.2849 0.0663 5 7 8 0.0952 0.0600 5 7 9 -0.0510 0.0119 5 8 5 0.1495 -0.0031 5 8 6 0.2792 -0.0649 5 8 7 0.1714 -0.0866 5 8 8 0.2158 -0.0377 5 9 5 0.0615 -0.0471 5 9 6 -0.0353 0.0459 6 0 6 -0.4400 -0.0770 6 0 8 0.4259 -0.1226 6 0 10 -0.0794 0.0471 6 0 12 -0.0991 0.0884 6 1 6 0.0478 0.0001 6 1 7 -0.1264 0.0994 6 1 8 0.1298 0.0289 6 1 9 -0.2218 0.0645 6 1 10 -0.1535 0.0590 6 1 11 0.1720 -0.0915 6 1 12 0.1602 0.0319 6 2 6 0.1690 -0.0089 6 2 7 -0.3402 0.0064 6 2 8 0.2103 -0.0613 6 2 9 0.2165 -0.0669 6 2 10 0.0324 -0.0082 6 2 11 -0.0941 -0.0761 6 2 12 -0.0549 0.0674 6 3 6 0.2198 -0.0007 6 3 7 -0.2485 0.0123 6 3 8 0.0005 0.0021 6 3 9 -0.0940 0.0218 6 3 10 -0.1086 0.0664 6 3 11 -0.1650 -0.0127 6 3 12 0.1504 0.0505 6 4 6 0.3992 0.0019 6 4 7 -0.1535 -0.0165 6 4 8 0.0252 -0.0331 6 4 9 0.0389 -0.0088 6 4 10 0.2437 0.0216 6 4 11 0.0686 -0.0624 6 5 6 0.0068 0.0328 6 5 7 -0.1705 0.0534 6 5 8 0.0606 0.0387 6 5 9 -0.0347 0.0107 6 5 10 -0.0539 0.0379 6 6 6 0.4638 -0.0305 6 6 7 0.1628 -0.0650 6 6 8 0.0633 -0.0612 6 6 9 0.0336 -0.0722 6 7 6 -0.2123 0.0595 6 7 7 -0.2452 0.0554 6 7 8 -0.2688 0.0891 6 8 6 0.0098 -0.0004 6 8 7 0.2124 -0.0668 7 0 7 -0.2302 -0.1167 7 0 9 0.4982 -0.1717 7 0 11 -0.0763 0.0713 7 1 7 0.1728 -0.0509 7 1 8 -0.3064 0.1505 7 1 9 -0.0188 0.0240 7 1 10 -0.1417 0.0536 7 1 11 -0.1390 0.0736 7 2 7 0.1944 -0.0221 7 2 8 -0.2005 0.0303 7 2 9 0.1399 -0.0642 7 2 10 0.3222 -0.0818 7 2 11 0.0401 0.0034 7 3 7 0.1729 -0.0204 7 3 8 -0.1110 0.0174 7 3 9 -0.2218 -0.0043 7 3 10 -0.1101 0.0254 7 3 11 -0.0779 0.0615 7 4 7 0.2066 -0.0186 7 4 8 0.0323 -0.0026 7 4 9 0.0560 -0.0466 7 4 10 0.0558 -0.0015 7 5 7 0.0181 0.0254 7 5 8 -0.1334 0.0876 7 5 9 0.0638 0.0324 7 6 7 0.3124 -0.0433 7 6 8 0.0223 -0.0585 7 6 9 0.1609 -0.0636 7 7 7 -0.0022 0.0273 7 7 8 -0.2024 0.0415 8 0 8 0.0062 -0.1478 8 0 10 0.4257 -0.1940 8 1 8 0.2961 -0.1013 8 1 9 -0.3836 0.1747 8 1 10 -0.0527 0.0209 8 2 8 0.2644 -0.0322 8 2 9 -0.0966 0.0357 8 2 10 0.0597 -0.0424 8 3 8 0.1401 -0.0200 8 3 9 0.0106 0.0052 8 3 10 -0.3195 0.0054 8 4 8 -0.0420 -0.0214 8 4 9 0.1912 0.0001 8 5 8 -0.0163 0.0125 8 6 8 0.0765 -0.0360 9 0 9 0.0711 -0.1698 9 1 9 0.3203 -0.1415 9 2 9 0.2790 -0.0397 9 3 9 0.1183 -0.0150 0 0 0 0.0 0.0 ; _shelx_fab_checksum 99324 _olex2_exptl_crystal_mounting_method 'polymer loop' _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.565 _oxdiff_exptl_absorpt_empirical_full_min 0.613 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 Cl1 Cl 0.46999(4) 0.17787(6) 0.28979(4) 0.02518(17) Uani 1 1 d . . . . . Cl2 Cl 0.07244(4) 0.32644(7) 0.07228(5) 0.03472(19) Uani 1 1 d . . . . . S1 S 0.65592(4) 0.59046(6) 0.56512(4) 0.01771(16) Uani 1 1 d . . . . . O1 O 0.58309(12) 0.5194(2) 0.22496(11) 0.0254(4) Uani 1 1 d . . . . . O2 O 1.19743(14) 0.6726(2) 0.70679(13) 0.0367(5) Uani 1 1 d . . . . . N1 N 0.55225(14) 0.5166(2) 0.37446(13) 0.0177(4) Uani 1 1 d . . . . . H1 H 0.503142 0.496470 0.399193 0.021 Uiso 1 1 calc R . . . . N2 N 0.72458(14) 0.5867(2) 0.40913(13) 0.0176(4) Uani 1 1 d . . . . . H2 H 0.708711 0.574660 0.343262 0.021 Uiso 1 1 calc R . . . . C1 C 0.52471(16) 0.4977(2) 0.27150(15) 0.0159(4) Uani 1 1 d . . . . . C2 C 0.64792(16) 0.5634(2) 0.44502(15) 0.0142(4) Uani 1 1 d . . . . . C3 C 0.82938(16) 0.6289(2) 0.46693(15) 0.0161(4) Uani 1 1 d . . . . . C4 C 0.88665(17) 0.5593(2) 0.55776(16) 0.0190(4) Uani 1 1 d . . . . . H4 H 0.854999 0.485258 0.584484 0.023 Uiso 1 1 calc R . . . . C5 C 0.99003(18) 0.5985(2) 0.60887(16) 0.0192(4) Uani 1 1 d . . . . . H5 H 1.029231 0.550923 0.670979 0.023 Uiso 1 1 calc R . . . . C6 C 1.03764(16) 0.7066(2) 0.57089(15) 0.0169(4) Uani 1 1 d . . . . . C7 C 0.97953(17) 0.7748(2) 0.47960(15) 0.0200(5) Uani 1 1 d . . . . . H7 H 1.011332 0.848259 0.452613 0.024 Uiso 1 1 calc R . . . . C8 C 0.87576(17) 0.7366(3) 0.42757(15) 0.0191(4) Uani 1 1 d . . . . . H8 H 0.836546 0.783882 0.365325 0.023 Uiso 1 1 calc R . . . . C9 C 1.15153(17) 0.7384(3) 0.62842(16) 0.0221(5) Uani 1 1 d . . . . . C10 C 1.2064(2) 0.8482(3) 0.5876(2) 0.0344(6) Uani 1 1 d . . . . . H10A H 1.275923 0.868321 0.638711 0.052 Uiso 1 1 calc GR . . . . H10B H 1.165400 0.939061 0.571595 0.052 Uiso 1 1 calc GR . . . . H10C H 1.214043 0.809812 0.525713 0.052 Uiso 1 1 calc GR . . . . C11 C 0.41216(16) 0.4531(2) 0.21957(14) 0.0153(4) Uani 1 1 d . . . . . C12 C 0.37919(17) 0.3096(2) 0.22465(14) 0.0154(4) Uani 1 1 d . . . . . C13 C 0.27521(17) 0.2697(2) 0.17931(15) 0.0176(4) Uani 1 1 d . . . . . H13 H 0.253516 0.171682 0.183000 0.021 Uiso 1 1 calc R . . . . C14 C 0.20331(17) 0.3763(3) 0.12832(16) 0.0200(5) Uani 1 1 d . . . . . C15 C 0.23323(18) 0.5189(2) 0.12009(16) 0.0215(5) Uani 1 1 d . . . . . H15 H 0.182819 0.590216 0.084130 0.026 Uiso 1 1 calc R . . . . C16 C 0.33830(18) 0.5559(2) 0.16538(16) 0.0205(5) Uani 1 1 d . . . . . H16 H 0.360084 0.653155 0.159226 0.025 Uiso 1 1 calc R . . . . 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 Cl1 0.0230(3) 0.0174(3) 0.0258(3) 0.00015(19) -0.0025(2) 0.00546(19) Cl2 0.0143(3) 0.0301(3) 0.0459(4) -0.0004(2) -0.0058(3) -0.0054(2) S1 0.0146(3) 0.0226(3) 0.0132(3) -0.00531(18) 0.0016(2) -0.00258(19) O1 0.0172(8) 0.0399(10) 0.0170(7) -0.0027(7) 0.0040(6) -0.0076(7) O2 0.0206(9) 0.0451(12) 0.0283(9) 0.0043(8) -0.0104(8) -0.0023(8) N1 0.0119(8) 0.0248(9) 0.0148(8) -0.0058(7) 0.0028(7) -0.0066(7) N2 0.0118(9) 0.0255(10) 0.0118(8) -0.0027(7) 0.0000(7) -0.0034(7) C1 0.0171(10) 0.0140(9) 0.0138(9) -0.0025(7) 0.0021(8) -0.0016(8) C2 0.0110(10) 0.0130(9) 0.0135(9) -0.0014(7) -0.0016(8) -0.0006(7) C3 0.0121(10) 0.0187(10) 0.0143(9) -0.0034(8) 0.0011(8) -0.0002(8) C4 0.0195(11) 0.0173(10) 0.0183(10) 0.0032(8) 0.0046(9) 0.0002(8) C5 0.0160(10) 0.0216(11) 0.0154(10) 0.0031(8) 0.0001(8) 0.0038(8) C6 0.0125(10) 0.0206(10) 0.0148(9) -0.0039(8) 0.0017(8) 0.0002(8) C7 0.0175(11) 0.0217(11) 0.0185(10) 0.0019(8) 0.0039(9) -0.0033(9) C8 0.0145(10) 0.0242(11) 0.0132(9) 0.0040(8) -0.0016(8) -0.0009(9) C9 0.0161(11) 0.0272(12) 0.0182(10) -0.0070(9) 0.0005(9) 0.0007(9) C10 0.0156(12) 0.0529(17) 0.0322(13) -0.0022(12) 0.0056(11) -0.0115(11) C11 0.0148(10) 0.0170(10) 0.0115(9) -0.0044(7) 0.0017(8) -0.0033(8) C12 0.0179(11) 0.0137(10) 0.0108(9) -0.0020(7) 0.0006(8) 0.0018(8) C13 0.0216(11) 0.0135(10) 0.0153(9) -0.0032(8) 0.0038(8) -0.0044(8) C14 0.0151(10) 0.0228(11) 0.0180(10) -0.0028(8) 0.0011(8) -0.0026(9) C15 0.0176(11) 0.0181(11) 0.0204(10) -0.0002(8) -0.0032(9) 0.0018(8) C16 0.0237(12) 0.0152(10) 0.0187(10) 0.0007(8) 0.0029(9) -0.0034(9) 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' Cl Cl 0.3639 0.7018 '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' O O 0.0492 0.0322 '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' loop_ _citation_id _citation_doi _citation_year 1 10.1039/D2RA03160D 2022 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 C1 N1 H1 115.8 . . ? C1 N1 C2 128.41(18) . . ? C2 N1 H1 115.8 . . ? C2 N2 H2 116.8 . . ? C2 N2 C3 126.36(17) . . ? C3 N2 H2 116.8 . . ? O1 C1 N1 124.45(19) . . ? O1 C1 C11 122.49(18) . . ? N1 C1 C11 113.01(17) . . ? N1 C2 S1 117.91(15) . . ? N2 C2 S1 125.86(15) . . ? N2 C2 N1 116.21(17) . . ? C4 C3 N2 121.3(2) . . ? C8 C3 N2 118.31(18) . . ? C8 C3 C4 120.3(2) . . ? C3 C4 H4 120.3 . . ? C5 C4 C3 119.4(2) . . ? C5 C4 H4 120.3 . . ? C4 C5 H5 119.5 . . ? C4 C5 C6 121.08(19) . . ? C6 C5 H5 119.5 . . ? C5 C6 C9 117.87(19) . . ? C7 C6 C5 118.9(2) . . ? C7 C6 C9 123.2(2) . . ? C6 C7 H7 119.6 . . ? C8 C7 C6 120.7(2) . . ? C8 C7 H7 119.6 . . ? C3 C8 H8 120.2 . . ? C7 C8 C3 119.63(19) . . ? C7 C8 H8 120.2 . . ? O2 C9 C6 119.4(2) . . ? O2 C9 C10 121.2(2) . . ? C10 C9 C6 119.4(2) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C1 121.51(19) . . ? C16 C11 C1 119.91(19) . . ? C16 C11 C12 118.58(19) . . ? C11 C12 Cl1 119.69(16) . . ? C13 C12 Cl1 118.86(16) . . ? C13 C12 C11 121.44(19) . . ? C12 C13 H13 120.8 . . ? C12 C13 C14 118.3(2) . . ? C14 C13 H13 120.8 . . ? C13 C14 Cl2 118.29(17) . . ? C15 C14 Cl2 119.77(18) . . ? C15 C14 C13 121.9(2) . . ? C14 C15 H15 120.7 . . ? C14 C15 C16 118.7(2) . . ? C16 C15 H15 120.7 . . ? C11 C16 H16 119.5 . . ? C15 C16 C11 121.0(2) . . ? C15 C16 H16 119.5 . . ? 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 Cl1 C12 1.734(2) . ? Cl2 C14 1.735(2) . ? S1 C2 1.673(2) . ? O1 C1 1.218(3) . ? O2 C9 1.213(3) . ? N1 H1 0.8800 . ? N1 C1 1.371(2) . ? N1 C2 1.394(3) . ? N2 H2 0.8800 . ? N2 C2 1.334(3) . ? N2 C3 1.422(3) . ? C1 C11 1.501(3) . ? C3 C4 1.389(3) . ? C3 C8 1.389(3) . ? C4 H4 0.9500 . ? C4 C5 1.382(3) . ? C5 H5 0.9500 . ? C5 C6 1.391(3) . ? C6 C7 1.390(3) . ? C6 C9 1.501(3) . ? C7 H7 0.9500 . ? C7 C8 1.385(3) . ? C8 H8 0.9500 . ? C9 C10 1.486(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.395(3) . ? C11 C16 1.388(3) . ? C12 C13 1.380(3) . ? C13 H13 0.9500 . ? C13 C14 1.385(3) . ? C14 C15 1.382(3) . ? C15 H15 0.9500 . ? C15 C16 1.386(3) . ? C16 H16 0.9500 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N1 H1 S1 0.88 2.53 3.3945(19) 167.8 3_666 yes N2 H2 O1 0.88 1.98 2.687(2) 136.7 . yes C7 H7 O1 0.95 2.83 3.498(3) 127.9 2_655 yes C8 H8 O2 0.95 2.39 3.290(3) 158.9 4_575 yes loop_ _smtbx_masks_void_nr _smtbx_masks_void_average_x _smtbx_masks_void_average_y _smtbx_masks_void_average_z _smtbx_masks_void_volume _smtbx_masks_void_count_electrons _smtbx_masks_void_content 1 0.126 0.599 0.877 15.5 0.3 ? 2 0.374 0.099 0.623 15.5 0.3 ? 3 0.626 0.901 0.377 15.5 0.3 ? 4 0.874 0.401 0.123 15.5 0.3 ?