#------------------------------------------------------------------------------ #$Date: 2023-11-22 04:12:53 +0200 (Wed, 22 Nov 2023) $ #$Revision: 287718 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247760.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_7247760 loop_ _publ_author_name 'Al-Wahaibi, Lamya H.' 'Alagappan, Kowsalya' 'Gomila, Rosa M.' 'Blacque, Olivier' 'Frontera, Antonio' 'Percino, M. Judith' 'El-Emam, Ali A.' 'Thamotharan, Subbiah' _publ_section_title ; A combined crystallographic and theoretical investigation of noncovalent interactions in 1,3,4-oxadiazole-2-thione-N-Mannich derivatives: in vitro bioactivity and molecular docking ; _journal_issue 48 _journal_name_full 'RSC Advances' _journal_page_first 34064 _journal_page_last 34077 _journal_paper_doi 10.1039/D3RA07169C _journal_volume 13 _journal_year 2023 _chemical_absolute_configuration ad _chemical_formula_moiety 'C16 H11 Cl F3 N3 O S' _chemical_formula_sum 'C16 H11 Cl F3 N3 O S' _chemical_formula_weight 385.79 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2021-01-04 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226) ; _audit_update_record ; 2023-10-18 deposited with the CCDC. 2023-11-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.7906(2) _cell_length_b 13.1169(6) _cell_length_c 25.4767(12) _cell_measurement_reflns_used 4484 _cell_measurement_temperature 160(1) _cell_measurement_theta_max 75.9680 _cell_measurement_theta_min 3.4900 _cell_volume 1600.90(12) _computing_cell_refinement 'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.68a' _computing_data_reduction 'CrysAlisPro 1.171.40.68a' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3' _computing_structure_refinement 'SHELXL (Sheldrick, 2015b)' _computing_structure_solution 'SHELXT (Sheldrick, 2015a)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 160(1) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.3801 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 -72.00 37.90 0.70 10.00 -- -38.50 19.00 -30.00 157 2 \w 27.00 97.00 0.70 10.00 -- 43.36-125.00 -90.00 100 3 \w 27.00 97.00 0.70 10.00 -- 43.36-125.00 120.00 100 4 \w 103.00 176.50 0.70 40.00 -- 111.00 77.00 120.00 105 5 \w 71.00 176.70 0.70 40.00 -- 111.00 15.00-180.00 151 6 \w 38.00 108.00 0.70 40.00 -- 111.00-111.00-150.00 100 7 \w 103.00 176.50 0.70 40.00 -- 111.00 77.00 90.00 105 8 \w 103.00 176.50 0.70 40.00 -- 111.00 77.00 0.00 105 9 \w 103.00 176.50 0.70 40.00 -- 111.00 77.00-180.00 105 10 \w 103.00 176.50 0.70 40.00 -- 111.00 77.00 150.00 105 11 \w 40.00 139.40 0.70 40.00 -- 111.00 -77.00 150.00 142 12 \w 38.00 108.00 0.70 40.00 -- 111.00-111.00-120.00 100 13 \w 40.00 139.40 0.70 40.00 -- 111.00 -77.00 0.00 142 14 \w 18.00 110.40 0.70 10.00 -- 43.36 57.00 30.00 132 15 \w 18.00 110.40 0.70 10.00 -- 43.36 57.00 -60.00 132 16 \w 18.00 110.40 0.70 10.00 -- 43.36 57.00-180.00 132 17 \w 89.00 176.50 0.70 40.00 -- 111.00 45.00-120.00 125 18 \w 85.00 176.70 0.70 40.00 -- 111.00 61.00 60.00 131 19 \w 90.00 176.80 0.70 40.00 -- 111.00 30.00 -60.00 124 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.1859274000 _diffrn_orient_matrix_UB_12 -0.0560956000 _diffrn_orient_matrix_UB_13 0.0401005000 _diffrn_orient_matrix_UB_21 0.2097463000 _diffrn_orient_matrix_UB_22 0.0257213000 _diffrn_orient_matrix_UB_23 0.0438694000 _diffrn_orient_matrix_UB_31 -0.1581054000 _diffrn_orient_matrix_UB_32 0.0999747000 _diffrn_orient_matrix_UB_33 0.0111605000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0711 _diffrn_reflns_av_unetI/netI 0.0460 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 15968 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.399 _diffrn_reflns_theta_min 3.470 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 3.741 _exptl_absorpt_correction_T_max 0.953 _exptl_absorpt_correction_T_min 0.632 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.601 _exptl_crystal_description needle _exptl_crystal_F_000 784 _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.378 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.053 _refine_ls_abs_structure_details ; Flack x determined using 1062 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.013(17) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 230 _refine_ls_number_reflns 3244 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0473 _refine_ls_R_factor_gt 0.0399 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0545P)^2^+0.2988P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0994 _refine_ls_wR_factor_ref 0.1042 _reflns_Friedel_coverage 0.685 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 0.997 _reflns_number_gt 2874 _reflns_number_total 3244 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ra07169c2.cif _cod_data_source_block emam-51 _cod_database_code 7247760 _shelx_shelxl_version_number 2018/3 _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 0.929 _shelx_estimated_absorpt_t_min 0.432 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2.a Secondary CH2 refined with riding coordinates: C9(H9A,H9B) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14) ; _shelx_res_file ; TITL emam-51_a.res in P2(1)2(1)2(1) emam-51.res created by SHELXL-2018/3 at 15:18:24 on 04-Jan-2021 CELL 1.54184 4.7906 13.1169 25.4767 90 90 90 ZERR 4 0.0002 0.0006 0.0012 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H Cl F N O S UNIT 64 44 4 12 12 4 4 EQIV $1 1-X,0.5+Y,1.5-Z L.S. 10 PLAN 20 SIZE 0.02 0.03 0.27 TEMP -113.1(10) CONF HTAB C5 F1_$1 HTAB N3 F3 MORE -1 BOND $H fmap 2 acta OMIT 0 2 0 REM REM REM WGHT 0.054500 0.298800 FVAR 4.35231 C1 1 -0.047776 0.347843 0.584851 11.00000 0.02421 0.03468 = 0.03705 -0.00537 0.00126 -0.00113 C2 1 0.026439 0.274347 0.621839 11.00000 0.03223 0.02605 = 0.04448 -0.00028 -0.00124 -0.00198 AFIX 43 H2 2 -0.057911 0.208810 0.621243 11.00000 -1.20000 AFIX 0 C3 1 0.226469 0.298320 0.659793 11.00000 0.03280 0.02895 = 0.04123 0.00245 -0.00208 -0.00192 AFIX 43 H3 2 0.280278 0.248774 0.685039 11.00000 -1.20000 AFIX 0 C4 1 0.345762 0.394071 0.660557 11.00000 0.02571 0.02920 = 0.03519 -0.00071 0.00226 0.00177 C5 1 0.266373 0.467823 0.623898 11.00000 0.03585 0.02835 = 0.03858 0.00182 -0.00074 -0.00260 AFIX 43 H5 2 0.348256 0.533757 0.624904 11.00000 -1.20000 AFIX 0 C6 1 0.067585 0.444740 0.585951 11.00000 0.03833 0.03132 = 0.03566 0.00261 -0.00212 0.00043 AFIX 43 H6 2 0.011556 0.494717 0.561104 11.00000 -1.20000 AFIX 0 C7 1 0.559136 0.417893 0.699930 11.00000 0.02787 0.02623 = 0.03357 -0.00365 0.00246 -0.00232 C8 1 0.881551 0.509097 0.739324 11.00000 0.02490 0.02948 = 0.03502 -0.00302 0.00237 0.00225 C9 1 0.995558 0.373802 0.807622 11.00000 0.02945 0.03524 = 0.03591 -0.00069 -0.00048 0.00714 AFIX 23 H9A 2 1.120832 0.319418 0.794541 11.00000 -1.20000 H9B 2 1.113173 0.427463 0.823673 11.00000 -1.20000 AFIX 0 C10 1 0.647558 0.394288 0.878072 11.00000 0.03052 0.03149 = 0.03086 -0.00145 -0.00400 0.00365 C11 1 0.665976 0.500907 0.875966 11.00000 0.03447 0.02945 = 0.03732 -0.00176 -0.00255 -0.00089 AFIX 43 H11 2 0.789261 0.531951 0.851520 11.00000 -1.20000 AFIX 0 C12 1 0.507672 0.561613 0.908880 11.00000 0.04017 0.02629 = 0.04608 -0.00432 -0.00253 0.00202 AFIX 43 H12 2 0.529549 0.633556 0.907645 11.00000 -1.20000 AFIX 0 C13 1 0.317346 0.519232 0.943692 11.00000 0.04373 0.03434 = 0.04098 -0.00392 0.00201 0.00524 AFIX 43 H13 2 0.204489 0.561578 0.965251 11.00000 -1.20000 AFIX 0 C14 1 0.294884 0.413714 0.946434 11.00000 0.03574 0.03775 = 0.03578 0.00030 0.00071 0.00132 AFIX 43 H14 2 0.167195 0.383806 0.970452 11.00000 -1.20000 AFIX 0 C15 1 0.456728 0.351406 0.914511 11.00000 0.03504 0.03087 = 0.03382 0.00119 -0.00593 0.00180 C16 1 0.431699 0.239072 0.918951 11.00000 0.03705 0.03315 = 0.04105 0.00388 -0.00138 0.00310 CL1 3 -0.291099 0.316594 0.537358 11.00000 0.03387 0.04036 = 0.04049 -0.00294 -0.00417 -0.00125 F1 4 0.676040 0.193039 0.931306 11.00000 0.04363 0.03353 = 0.05732 0.00737 -0.00951 0.00720 F2 4 0.250542 0.208788 0.956199 11.00000 0.05635 0.03761 = 0.06444 0.00699 0.01243 -0.00910 F3 4 0.347499 0.193820 0.874165 11.00000 0.05614 0.02963 = 0.05250 -0.00474 -0.01240 0.00014 N1 5 0.637204 0.359823 0.738092 11.00000 0.03008 0.02749 = 0.03849 -0.00173 -0.00097 0.00069 N2 5 0.839367 0.418071 0.762648 11.00000 0.03100 0.02759 = 0.03545 -0.00241 -0.00019 0.00233 N3 5 0.815709 0.332385 0.846668 11.00000 0.03939 0.02633 = 0.03646 -0.00140 0.00165 0.00458 H3A 2 0.769466 0.267628 0.841536 11.00000 0.03522 O1 6 0.696699 0.508800 0.697784 11.00000 0.03205 0.02794 = 0.03648 -0.00057 0.00021 -0.00005 S1 7 1.095269 0.603149 0.752924 11.00000 0.03459 0.03142 = 0.04839 -0.00624 -0.00037 -0.00371 HKLF 4 REM emam-51_a.res in P2(1)2(1)2(1) REM wR2 = 0.1042, GooF = S = 1.035, Restrained GooF = 1.035 for all data REM R1 = 0.0399 for 2874 Fo > 4sig(Fo) and 0.0473 for all 3244 data REM 230 parameters refined using 0 restraints END WGHT 0.0545 0.2988 REM Highest difference peak 0.378, deepest hole -0.321, 1-sigma level 0.053 Q1 1 1.0990 0.6016 0.7916 11.00000 0.05 0.38 Q2 1 1.0950 0.6028 0.7149 11.00000 0.05 0.36 Q3 1 -0.2927 0.3187 0.5732 11.00000 0.05 0.36 Q4 1 -0.2876 0.3190 0.4991 11.00000 0.05 0.30 Q5 1 0.9556 0.5526 0.7514 11.00000 0.05 0.26 Q6 1 0.0141 0.2837 0.5874 11.00000 0.05 0.23 Q7 1 0.4511 0.3042 0.9140 11.00000 0.05 0.21 Q8 1 0.6838 0.1986 0.8929 11.00000 0.05 0.20 Q9 1 0.2990 0.4236 0.8752 11.00000 0.05 0.19 Q10 1 0.4717 0.3565 0.8832 11.00000 0.05 0.19 Q11 1 -0.4192 0.3809 0.5401 11.00000 0.05 0.19 Q12 1 0.6038 0.2988 0.7482 11.00000 0.05 0.18 Q13 1 0.3505 0.4023 0.6270 11.00000 0.05 0.18 Q14 1 0.0143 0.3971 0.5848 11.00000 0.05 0.18 Q15 1 -0.0667 0.3205 0.6162 11.00000 0.05 0.18 Q16 1 0.6596 0.5084 0.9173 11.00000 0.05 0.18 Q17 1 0.6624 0.3608 0.7039 11.00000 0.05 0.18 Q18 1 0.1065 0.4626 0.5468 11.00000 0.05 0.17 Q19 1 -0.2959 0.3153 0.6184 11.00000 0.05 0.17 Q20 1 0.3271 0.5244 0.9142 11.00000 0.05 0.17 ; _shelx_res_checksum 51798 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -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 C1 C -0.0478(8) 0.3478(3) 0.58485(16) 0.0320(8) Uani 1 1 d . . . . . C2 C 0.0264(8) 0.2743(3) 0.62184(18) 0.0343(8) Uani 1 1 d . . . . . H2 H -0.057911 0.208810 0.621243 0.041 Uiso 1 1 calc R U . . . C3 C 0.2265(9) 0.2983(3) 0.65979(16) 0.0343(8) Uani 1 1 d . . . . . H3 H 0.280278 0.248774 0.685039 0.041 Uiso 1 1 calc R U . . . C4 C 0.3458(8) 0.3941(3) 0.66056(15) 0.0300(8) Uani 1 1 d . . . . . C5 C 0.2664(9) 0.4678(3) 0.62390(17) 0.0343(8) Uani 1 1 d . . . . . H5 H 0.348256 0.533757 0.624904 0.041 Uiso 1 1 calc R U . . . C6 C 0.0676(9) 0.4447(3) 0.58595(16) 0.0351(9) Uani 1 1 d . . . . . H6 H 0.011556 0.494717 0.561104 0.042 Uiso 1 1 calc R U . . . C7 C 0.5591(8) 0.4179(3) 0.69993(15) 0.0292(8) Uani 1 1 d . . . . . C8 C 0.8816(8) 0.5091(3) 0.73932(15) 0.0298(8) Uani 1 1 d . . . . . C9 C 0.9956(8) 0.3738(3) 0.80762(16) 0.0335(8) Uani 1 1 d . . . . . H9A H 1.120832 0.319418 0.794541 0.040 Uiso 1 1 calc R U . . . H9B H 1.113173 0.427463 0.823673 0.040 Uiso 1 1 calc R U . . . C10 C 0.6476(8) 0.3943(3) 0.87807(15) 0.0310(8) Uani 1 1 d . . . . . C11 C 0.6660(8) 0.5009(3) 0.87597(16) 0.0337(8) Uani 1 1 d . . . . . H11 H 0.789261 0.531951 0.851520 0.040 Uiso 1 1 calc R U . . . C12 C 0.5077(9) 0.5616(3) 0.90888(18) 0.0375(9) Uani 1 1 d . . . . . H12 H 0.529549 0.633556 0.907645 0.045 Uiso 1 1 calc R U . . . C13 C 0.3173(10) 0.5192(3) 0.94369(17) 0.0397(9) Uani 1 1 d . . . . . H13 H 0.204489 0.561578 0.965251 0.048 Uiso 1 1 calc R U . . . C14 C 0.2949(10) 0.4137(3) 0.94643(16) 0.0364(9) Uani 1 1 d . . . . . H14 H 0.167195 0.383806 0.970452 0.044 Uiso 1 1 calc R U . . . C15 C 0.4567(9) 0.3514(3) 0.91451(16) 0.0332(9) Uani 1 1 d . . . . . C16 C 0.4317(10) 0.2391(3) 0.91895(18) 0.0371(9) Uani 1 1 d . . . . . Cl1 Cl -0.2911(2) 0.31659(8) 0.53736(4) 0.0382(2) Uani 1 1 d . . . . . F1 F 0.6760(6) 0.1930(2) 0.93131(11) 0.0448(6) Uani 1 1 d . . . . . F2 F 0.2505(6) 0.2088(2) 0.95620(12) 0.0528(7) Uani 1 1 d . . . . . F3 F 0.3475(6) 0.19382(19) 0.87417(11) 0.0461(6) Uani 1 1 d . . . . . N1 N 0.6372(7) 0.3598(2) 0.73809(13) 0.0320(7) Uani 1 1 d . . . . . N2 N 0.8394(7) 0.4181(2) 0.76265(13) 0.0313(7) Uani 1 1 d . . . . . N3 N 0.8157(8) 0.3324(3) 0.84667(14) 0.0341(7) Uani 1 1 d . . . . . H3A H 0.769(11) 0.268(4) 0.8415(19) 0.035(12) Uiso 1 1 d . . . . . O1 O 0.6967(6) 0.5088(2) 0.69778(11) 0.0322(6) Uani 1 1 d . . . . . S1 S 1.0953(2) 0.60315(8) 0.75292(5) 0.0381(2) 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 C1 0.0242(18) 0.035(2) 0.037(2) -0.0054(16) 0.0013(14) -0.0011(14) C2 0.0322(19) 0.0260(19) 0.044(2) -0.0003(17) -0.0012(16) -0.0020(15) C3 0.0328(19) 0.0289(19) 0.041(2) 0.0025(16) -0.0021(16) -0.0019(16) C4 0.0257(18) 0.0292(18) 0.0352(19) -0.0007(16) 0.0023(14) 0.0018(14) C5 0.036(2) 0.0284(18) 0.039(2) 0.0018(16) -0.0007(17) -0.0026(16) C6 0.038(2) 0.031(2) 0.036(2) 0.0026(16) -0.0021(17) 0.0004(17) C7 0.0279(18) 0.0262(19) 0.0336(19) -0.0037(15) 0.0025(15) -0.0023(14) C8 0.0249(17) 0.0295(18) 0.035(2) -0.0030(15) 0.0024(14) 0.0023(14) C9 0.0295(18) 0.035(2) 0.0359(19) -0.0007(16) -0.0005(15) 0.0071(16) C10 0.0305(19) 0.0315(18) 0.0309(17) -0.0015(16) -0.0040(14) 0.0036(15) C11 0.034(2) 0.0294(19) 0.037(2) -0.0018(16) -0.0025(16) -0.0009(16) C12 0.040(2) 0.026(2) 0.046(2) -0.0043(17) -0.0025(18) 0.0020(17) C13 0.044(2) 0.034(2) 0.041(2) -0.0039(17) 0.0020(18) 0.0052(18) C14 0.036(2) 0.038(2) 0.0358(19) 0.0003(16) 0.0007(16) 0.0013(17) C15 0.035(2) 0.031(2) 0.034(2) 0.0012(16) -0.0059(16) 0.0018(15) C16 0.037(2) 0.033(2) 0.041(2) 0.0039(17) -0.0014(17) 0.0031(17) Cl1 0.0339(4) 0.0404(5) 0.0405(5) -0.0029(4) -0.0042(4) -0.0012(4) F1 0.0436(14) 0.0335(12) 0.0573(15) 0.0074(12) -0.0095(12) 0.0072(11) F2 0.0563(17) 0.0376(14) 0.0644(17) 0.0070(12) 0.0124(14) -0.0091(12) F3 0.0561(16) 0.0296(12) 0.0525(14) -0.0047(11) -0.0124(12) 0.0001(12) N1 0.0301(17) 0.0275(15) 0.0385(18) -0.0017(13) -0.0010(13) 0.0007(12) N2 0.0310(17) 0.0276(15) 0.0355(17) -0.0024(13) -0.0002(13) 0.0023(12) N3 0.0394(18) 0.0263(17) 0.0365(17) -0.0014(13) 0.0017(14) 0.0046(14) O1 0.0320(13) 0.0279(13) 0.0365(14) -0.0006(11) 0.0002(11) -0.0001(11) S1 0.0346(5) 0.0314(5) 0.0484(6) -0.0062(4) -0.0004(4) -0.0037(4) 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' F F 0.0727 0.0534 '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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.0117 0 0 -1 0.0047 0 -1 1 0.0010 0 1 -1 0.0155 1 -1 -5 0.0899 -1 0 1 0.1294 3 1 -2 0.1388 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 C2 C1 Cl1 118.7(3) . . ? C6 C1 C2 121.2(4) . . ? C6 C1 Cl1 120.0(3) . . ? C1 C2 H2 120.4 . . ? C1 C2 C3 119.1(4) . . ? C3 C2 H2 120.4 . . ? C2 C3 H3 120.0 . . ? C4 C3 C2 119.9(4) . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 120.5(4) . . ? C3 C4 C7 119.5(4) . . ? C5 C4 C7 120.0(4) . . ? C4 C5 H5 120.0 . . ? C6 C5 C4 120.0(4) . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 119.1(4) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? N1 C7 C4 126.3(4) . . ? N1 C7 O1 114.0(3) . . ? O1 C7 C4 119.7(3) . . ? N2 C8 O1 103.8(3) . . ? N2 C8 S1 131.8(3) . . ? O1 C8 S1 124.4(3) . . ? H9A C9 H9B 107.8 . . ? N2 C9 H9A 109.1 . . ? N2 C9 H9B 109.1 . . ? N3 C9 H9A 109.1 . . ? N3 C9 H9B 109.1 . . ? N3 C9 N2 112.5(3) . . ? C11 C10 C15 117.4(4) . . ? N3 C10 C11 121.5(4) . . ? N3 C10 C15 121.1(4) . . ? C10 C11 H11 119.4 . . ? C12 C11 C10 121.1(4) . . ? C12 C11 H11 119.4 . . ? C11 C12 H12 119.4 . . ? C11 C12 C13 121.1(4) . . ? C13 C12 H12 119.4 . . ? C12 C13 H13 120.6 . . ? C12 C13 C14 118.8(4) . . ? C14 C13 H13 120.6 . . ? C13 C14 H14 119.6 . . ? C15 C14 C13 120.9(4) . . ? C15 C14 H14 119.6 . . ? C10 C15 C16 119.7(4) . . ? C14 C15 C10 120.6(4) . . ? C14 C15 C16 119.7(4) . . ? F1 C16 C15 113.0(4) . . ? F2 C16 C15 113.5(4) . . ? F2 C16 F1 105.2(4) . . ? F2 C16 F3 105.9(4) . . ? F3 C16 C15 113.4(4) . . ? F3 C16 F1 105.0(4) . . ? C7 N1 N2 102.6(3) . . ? C8 N2 C9 127.6(3) . . ? C8 N2 N1 113.2(3) . . ? N1 N2 C9 119.0(3) . . ? C9 N3 H3A 114(3) . . ? C10 N3 C9 121.9(4) . . ? C10 N3 H3A 120(3) . . ? C7 O1 C8 106.4(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 C1 C2 1.394(6) . ? C1 C6 1.386(6) . ? C1 Cl1 1.729(4) . ? C2 H2 0.9500 . ? C2 C3 1.397(6) . ? C3 H3 0.9500 . ? C3 C4 1.380(6) . ? C4 C5 1.397(6) . ? C4 C7 1.466(6) . ? C5 H5 0.9500 . ? C5 C6 1.390(6) . ? C6 H6 0.9500 . ? C7 N1 1.290(5) . ? C7 O1 1.364(5) . ? C8 N2 1.349(5) . ? C8 O1 1.380(5) . ? C8 S1 1.640(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C9 N2 1.487(5) . ? C9 N3 1.424(6) . ? C10 C11 1.402(6) . ? C10 C15 1.419(6) . ? C10 N3 1.396(5) . ? C11 H11 0.9500 . ? C11 C12 1.383(6) . ? C12 H12 0.9500 . ? C12 C13 1.388(6) . ? C13 H13 0.9500 . ? C13 C14 1.390(6) . ? C14 H14 0.9500 . ? C14 C15 1.389(6) . ? C15 C16 1.483(6) . ? C16 F1 1.354(5) . ? C16 F2 1.346(6) . ? C16 F3 1.348(5) . ? N1 N2 1.383(5) . ? N3 H3A 0.89(5) . ? 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 C5 H5 F1 0.95 2.54 3.283(5) 135.7 3_656 yes N3 H3A F3 0.89(5) 2.39(5) 2.971(5) 123(4) . yes 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 C1 C2 C3 C4 0.6(6) . . . . ? C2 C1 C6 C5 1.7(7) . . . . ? C2 C3 C4 C5 0.6(6) . . . . ? C2 C3 C4 C7 -178.9(4) . . . . ? C3 C4 C5 C6 -0.6(6) . . . . ? C3 C4 C7 N1 -5.8(6) . . . . ? C3 C4 C7 O1 173.8(4) . . . . ? C4 C5 C6 C1 -0.5(7) . . . . ? C4 C7 N1 N2 180.0(4) . . . . ? C4 C7 O1 C8 180.0(3) . . . . ? C5 C4 C7 N1 174.8(4) . . . . ? C5 C4 C7 O1 -5.7(6) . . . . ? C6 C1 C2 C3 -1.7(6) . . . . ? C7 C4 C5 C6 178.9(4) . . . . ? C7 N1 N2 C8 -0.3(4) . . . . ? C7 N1 N2 C9 -176.2(3) . . . . ? C10 C11 C12 C13 -2.5(7) . . . . ? C10 C15 C16 F1 58.1(5) . . . . ? C10 C15 C16 F2 177.8(4) . . . . ? C10 C15 C16 F3 -61.2(5) . . . . ? C11 C10 C15 C14 0.3(6) . . . . ? C11 C10 C15 C16 -179.1(4) . . . . ? C11 C10 N3 C9 -5.8(6) . . . . ? C11 C12 C13 C14 2.3(7) . . . . ? C12 C13 C14 C15 -0.9(7) . . . . ? C13 C14 C15 C10 -0.4(6) . . . . ? C13 C14 C15 C16 179.0(4) . . . . ? C14 C15 C16 F1 -121.3(4) . . . . ? C14 C15 C16 F2 -1.6(6) . . . . ? C14 C15 C16 F3 119.4(4) . . . . ? C15 C10 C11 C12 1.2(6) . . . . ? C15 C10 N3 C9 176.0(4) . . . . ? Cl1 C1 C2 C3 178.9(3) . . . . ? Cl1 C1 C6 C5 -178.9(3) . . . . ? N1 C7 O1 C8 -0.4(4) . . . . ? N2 C8 O1 C7 0.2(4) . . . . ? N2 C9 N3 C10 -69.2(5) . . . . ? N3 C9 N2 C8 133.4(4) . . . . ? N3 C9 N2 N1 -51.4(5) . . . . ? N3 C10 C11 C12 -177.1(4) . . . . ? N3 C10 C15 C14 178.5(4) . . . . ? N3 C10 C15 C16 -0.9(6) . . . . ? O1 C7 N1 N2 0.4(4) . . . . ? O1 C8 N2 C9 175.5(3) . . . . ? O1 C8 N2 N1 0.0(4) . . . . ? S1 C8 N2 C9 -4.0(6) . . . . ? S1 C8 N2 N1 -179.5(3) . . . . ? S1 C8 O1 C7 179.8(3) . . . . ?