#------------------------------------------------------------------------------ #$Date: 2023-11-22 04:12:53 +0200 (Wed, 22 Nov 2023) $ #$Revision: 287718 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247761.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_7247761 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 'C15 H10 Cl F2 N3 O S' _chemical_formula_sum 'C15 H10 Cl F2 N3 O S' _chemical_formula_weight 353.77 _space_group_crystal_system orthorhombic _space_group_IT_number 45 _space_group_name_Hall 'I 2 -2c' _space_group_name_H-M_alt 'I b a 2' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2021-01-07 _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 8 _cell_length_a 28.8781(9) _cell_length_b 13.8936(4) _cell_length_c 7.7325(3) _cell_measurement_reflns_used 5035 _cell_measurement_temperature 160(1) _cell_measurement_theta_max 76.0830 _cell_measurement_theta_min 3.0520 _cell_volume 3102.44(18) _computing_cell_refinement 'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _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 1.000 _diffrn_measured_fraction_theta_max 1.000 _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 -107.00 -13.00 1.00 7.00 -- -38.50 -57.00 0.00 94 2 \w -27.00 64.00 1.00 7.00 -- 43.74 -37.00 150.00 91 3 \w 24.00 95.00 1.00 7.00 -- 43.74-121.00 113.00 71 4 \w 40.00 110.00 1.00 28.00 -- 111.00-121.00 113.00 70 5 \w 61.00 146.00 1.00 28.00 -- 111.00 178.00 -90.00 85 6 \w 43.00 137.00 1.00 28.00 -- 111.00 -61.00 0.00 94 7 \w 90.00 178.00 1.00 28.00 -- 111.00 30.00 -60.00 88 8 \w 38.00 109.00 1.00 28.00 -- 111.00-111.00 -60.00 71 9 \w 104.00 178.00 1.00 28.00 -- 111.00 111.00-150.00 74 10 \w 31.00 107.00 1.00 28.00 -- 111.00 -94.00 150.00 76 11 \w 89.00 178.00 1.00 28.00 -- 111.00 45.00-180.00 89 12 \w 31.00 107.00 1.00 28.00 -- 111.00 -94.00-150.00 76 13 \w 19.00 112.00 1.00 7.00 -- 43.74 57.00 150.00 93 14 \w 19.00 112.00 1.00 7.00 -- 43.74 57.00 -90.00 93 15 \w 71.00 178.00 1.00 28.00 -- 111.00 15.00 90.00 107 16 \w 85.00 178.00 1.00 28.00 -- 111.00 61.00 0.00 93 17 \w 89.00 178.00 1.00 28.00 -- 111.00 45.00-120.00 89 18 \w 31.00 73.00 1.00 28.00 -- 111.00 -94.00 -30.00 42 19 \w 103.00 178.00 1.00 28.00 -- 111.00 77.00 120.00 75 ; _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 -0.0220707000 _diffrn_orient_matrix_UB_12 -0.0170183000 _diffrn_orient_matrix_UB_13 -0.1788621000 _diffrn_orient_matrix_UB_21 -0.0479490000 _diffrn_orient_matrix_UB_22 -0.0099004000 _diffrn_orient_matrix_UB_23 0.0856730000 _diffrn_orient_matrix_UB_31 -0.0077831000 _diffrn_orient_matrix_UB_32 0.1090439000 _diffrn_orient_matrix_UB_33 -0.0202224000 _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 0.0466 _diffrn_reflns_av_unetI/netI 0.0326 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 15474 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.430 _diffrn_reflns_theta_min 3.061 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 3.709 _exptl_absorpt_correction_T_max 0.941 _exptl_absorpt_correction_T_min 0.745 _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 1.515 _exptl_crystal_description needle _exptl_crystal_F_000 1440 _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.179 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.036 _refine_ls_abs_structure_details ; Flack x determined using 1217 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.004(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 212 _refine_ls_number_reflns 3163 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.061 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0270 _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^)+(0.0258P)^2^+0.3772P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.0607 _reflns_Friedel_coverage 0.845 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.997 _reflns_number_gt 2856 _reflns_number_total 3163 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ra07169c2.cif _cod_data_source_block emam-52 _cod_original_cell_volume 3102.43(17) _cod_database_code 7247761 _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 0.930 _shelx_estimated_absorpt_t_min 0.686 _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), C12(H12), C13(H13), C15(H15) ; _shelx_res_file ; TITL emam-52_a.res in Iba2 emam-52.res created by SHELXL-2018/3 at 15:04:14 on 07-Jan-2021 CELL 1.54184 28.878104 13.89363 7.73245 90 90 90 ZERR 8 0.000891 0.000385 0.000263 0 0 0 LATT -2 SYMM -X,-Y,+Z SYMM 0.5+X,0.5-Y,+Z SYMM 0.5-X,0.5+Y,+Z SFAC C H Cl F N O S UNIT 120 80 8 16 24 8 8 L.S. 10 PLAN 20 SIZE 0.02 0.05 0.11 TEMP -113.1(10) CONF BOND $H MORE -1 fmap 2 acta REM REM REM WGHT 0.025800 0.377200 FVAR 1.88216 C1 1 0.552737 0.658425 0.302611 11.00000 0.02476 0.04282 = 0.02462 0.00255 -0.00112 0.00226 C2 1 0.566080 0.564638 0.335370 11.00000 0.02977 0.03688 = 0.03469 -0.00650 0.00079 -0.00502 AFIX 43 H2 2 0.549058 0.512230 0.288621 11.00000 -1.20000 AFIX 0 C3 1 0.604590 0.548418 0.437247 11.00000 0.02939 0.02519 = 0.03599 -0.00259 0.00248 0.00009 AFIX 43 H3 2 0.614324 0.484421 0.460703 11.00000 -1.20000 AFIX 0 C4 1 0.629148 0.625826 0.505574 11.00000 0.02341 0.02699 = 0.02492 0.00008 0.00243 -0.00019 C5 1 0.614771 0.719643 0.473921 11.00000 0.02766 0.02510 = 0.02907 0.00152 0.00405 -0.00206 AFIX 43 H5 2 0.631308 0.772251 0.522345 11.00000 -1.20000 AFIX 0 C6 1 0.576294 0.736106 0.371642 11.00000 0.03121 0.03082 = 0.02935 0.00541 0.00494 0.00383 AFIX 43 H6 2 0.566175 0.799946 0.349095 11.00000 -1.20000 AFIX 0 C7 1 0.671269 0.609140 0.605912 11.00000 0.02602 0.02108 = 0.02547 0.00188 0.00298 0.00074 C8 1 0.725142 0.520475 0.726101 11.00000 0.02510 0.02379 = 0.02169 0.00074 0.00066 -0.00239 C9 1 0.773638 0.661112 0.826636 11.00000 0.03015 0.02473 = 0.02988 -0.00317 -0.00465 -0.00137 AFIX 23 H9A 2 0.762496 0.705091 0.918376 11.00000 -1.20000 H9B 2 0.793034 0.611135 0.882148 11.00000 -1.20000 AFIX 0 C10 1 0.836750 0.675105 0.611930 11.00000 0.02747 0.02519 = 0.02965 -0.00030 -0.00869 -0.00257 C11 1 0.863885 0.736141 0.510958 11.00000 0.04167 0.02242 = 0.03160 0.00114 -0.00738 -0.00456 C12 1 0.900843 0.706843 0.414628 11.00000 0.04769 0.04453 = 0.02999 0.00422 -0.00017 -0.01045 AFIX 43 H12 2 0.918378 0.752078 0.349826 11.00000 -1.20000 AFIX 0 C13 1 0.912474 0.609603 0.412732 11.00000 0.04515 0.05313 = 0.03497 -0.00710 0.00679 0.00461 AFIX 43 H13 2 0.937940 0.586296 0.347194 11.00000 -1.20000 AFIX 0 C14 1 0.885476 0.549041 0.509828 11.00000 0.04496 0.02810 = 0.03817 -0.00402 -0.00479 0.00573 C15 1 0.848438 0.577847 0.608657 11.00000 0.03232 0.02469 = 0.03552 -0.00043 -0.00381 -0.00188 AFIX 43 H15 2 0.831124 0.532282 0.673543 11.00000 -1.20000 AFIX 0 CL1 3 0.504953 0.678717 0.170801 11.00000 0.03321 0.06335 = 0.03799 0.00780 -0.00961 -0.00064 F1 4 0.852613 0.831695 0.515028 11.00000 0.05937 0.02497 = 0.04691 0.00510 -0.00167 -0.00768 F2 4 0.895657 0.452837 0.507708 11.00000 0.06756 0.03546 = 0.06055 -0.00481 0.00785 0.01686 N1 5 0.699773 0.670961 0.667026 11.00000 0.02685 0.02229 = 0.02768 0.00078 -0.00107 0.00123 N2 5 0.733676 0.614870 0.743988 11.00000 0.02457 0.02114 = 0.02900 -0.00136 -0.00134 -0.00020 N3 5 0.801105 0.713848 0.708001 11.00000 0.03117 0.01752 = 0.04693 -0.00018 -0.00091 -0.00257 H3A 2 0.796860 0.770291 0.708905 11.00000 0.02685 O1 6 0.684001 0.515501 0.637985 11.00000 0.02582 0.02032 = 0.03072 0.00227 -0.00127 -0.00246 S1 7 0.754611 0.425252 0.790131 11.00000 0.03161 0.02195 = 0.03511 0.00520 -0.00294 -0.00035 HKLF 4 REM emam-52_a.res in Iba2 REM wR2 = 0.0607, GooF = S = 1.061, Restrained GooF = 1.061 for all data REM R1 = 0.0270 for 2856 Fo > 4sig(Fo) and 0.0334 for all 3163 data REM 212 parameters refined using 1 restraints END WGHT 0.0258 0.3772 REM Highest difference peak 0.179, deepest hole -0.157, 1-sigma level 0.036 Q1 1 0.6491 0.6163 0.5534 11.00000 0.05 0.18 Q2 1 1.0000 0.5000 0.1757 10.50000 0.05 0.16 Q3 1 0.6208 0.5912 0.4681 11.00000 0.05 0.15 Q4 1 0.5683 0.6898 0.3387 11.00000 0.05 0.14 Q5 1 0.8505 0.7012 0.5592 11.00000 0.05 0.14 Q6 1 0.7146 0.7737 0.8625 11.00000 0.05 0.14 Q7 1 0.7067 0.5199 0.6833 11.00000 0.05 0.13 Q8 1 0.8114 0.5028 0.8953 11.00000 0.05 0.13 Q9 1 0.5012 0.7554 0.1823 11.00000 0.05 0.13 Q10 1 0.8505 0.6644 0.6521 11.00000 0.05 0.13 Q11 1 0.5639 0.6152 0.3094 11.00000 0.05 0.13 Q12 1 0.7523 0.6350 0.7808 11.00000 0.05 0.13 Q13 1 0.8616 0.5631 0.5451 11.00000 0.05 0.13 Q14 1 0.5922 0.7268 0.4498 11.00000 0.05 0.12 Q15 1 0.6310 0.6524 0.4831 11.00000 0.05 0.12 Q16 1 0.9301 0.4355 0.4163 11.00000 0.05 0.12 Q17 1 0.6019 0.7360 0.6530 11.00000 0.05 0.12 Q18 1 0.7151 0.6446 0.7003 11.00000 0.05 0.12 Q19 1 0.6841 0.8489 0.6738 11.00000 0.05 0.11 Q20 1 0.6484 0.7960 0.5121 11.00000 0.05 0.11 ; _shelx_res_checksum 53652 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1, -y+1, z+1/2' '-x+1, y+1, 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 C1 C 0.55274(9) 0.6584(2) 0.3026(4) 0.0307(6) Uani 1 1 d . . . . . C2 C 0.56608(10) 0.5646(2) 0.3354(4) 0.0338(6) Uani 1 1 d . . . . . H2 H 0.549058 0.512230 0.288621 0.041 Uiso 1 1 calc R U . . . C3 C 0.60459(9) 0.5484(2) 0.4372(4) 0.0302(6) Uani 1 1 d . . . . . H3 H 0.614324 0.484421 0.460703 0.036 Uiso 1 1 calc R U . . . C4 C 0.62915(9) 0.6258(2) 0.5056(4) 0.0251(5) Uani 1 1 d . . . . . C5 C 0.61477(9) 0.7196(2) 0.4739(4) 0.0273(6) Uani 1 1 d . . . . . H5 H 0.631308 0.772251 0.522345 0.033 Uiso 1 1 calc R U . . . C6 C 0.57629(10) 0.7361(2) 0.3716(4) 0.0305(6) Uani 1 1 d . . . . . H6 H 0.566175 0.799946 0.349095 0.037 Uiso 1 1 calc R U . . . C7 C 0.67127(9) 0.6091(2) 0.6059(3) 0.0242(5) Uani 1 1 d . . . . . C8 C 0.72514(8) 0.52048(19) 0.7261(3) 0.0235(5) Uani 1 1 d . . . . . C9 C 0.77364(9) 0.6611(2) 0.8266(4) 0.0283(6) Uani 1 1 d . . . . . H9A H 0.762496 0.705091 0.918376 0.034 Uiso 1 1 calc R U . . . H9B H 0.793034 0.611135 0.882148 0.034 Uiso 1 1 calc R U . . . C10 C 0.83675(9) 0.6751(2) 0.6119(4) 0.0274(6) Uani 1 1 d . . . . . C11 C 0.86389(11) 0.7361(2) 0.5110(4) 0.0319(6) Uani 1 1 d . . . . . C12 C 0.90084(12) 0.7068(2) 0.4146(5) 0.0407(7) Uani 1 1 d . . . . . H12 H 0.918378 0.752078 0.349826 0.049 Uiso 1 1 calc R U . . . C13 C 0.91247(12) 0.6096(3) 0.4127(5) 0.0444(8) Uani 1 1 d . . . . . H13 H 0.937940 0.586296 0.347194 0.053 Uiso 1 1 calc R U . . . C14 C 0.88548(12) 0.5490(2) 0.5098(5) 0.0371(7) Uani 1 1 d . . . . . C15 C 0.84844(10) 0.5778(2) 0.6087(4) 0.0308(6) Uani 1 1 d . . . . . H15 H 0.831124 0.532282 0.673543 0.037 Uiso 1 1 calc R U . . . Cl1 Cl 0.50495(2) 0.67872(6) 0.17080(11) 0.04485(19) Uani 1 1 d . . . . . F1 F 0.85261(8) 0.83169(13) 0.5150(3) 0.0438(5) Uani 1 1 d . . . . . F2 F 0.89566(9) 0.45284(15) 0.5077(3) 0.0545(6) Uani 1 1 d . . . . . N1 N 0.69977(7) 0.67096(16) 0.6670(3) 0.0256(4) Uani 1 1 d . . . . . N2 N 0.73368(7) 0.61487(16) 0.7440(3) 0.0249(5) Uani 1 1 d . . . . . N3 N 0.80110(8) 0.71385(18) 0.7080(4) 0.0319(6) Uani 1 1 d . . . . . H3A H 0.7969(11) 0.770(3) 0.709(4) 0.027(9) Uiso 1 1 d . . . . . O1 O 0.68400(6) 0.51550(13) 0.6380(2) 0.0256(4) Uani 1 1 d . . . . . S1 S 0.75461(2) 0.42525(5) 0.79013(10) 0.02956(14) 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 0.0248(11) 0.0428(15) 0.0246(12) 0.0025(13) -0.0011(11) 0.0023(11) C2 0.0298(13) 0.0369(16) 0.0347(15) -0.0065(13) 0.0008(11) -0.0050(12) C3 0.0294(12) 0.0252(13) 0.0360(15) -0.0026(12) 0.0025(12) 0.0001(11) C4 0.0234(12) 0.0270(14) 0.0249(13) 0.0001(12) 0.0024(10) -0.0002(10) C5 0.0277(12) 0.0251(14) 0.0291(14) 0.0015(11) 0.0041(11) -0.0021(11) C6 0.0312(14) 0.0308(14) 0.0293(15) 0.0054(11) 0.0049(12) 0.0038(12) C7 0.0260(12) 0.0211(12) 0.0255(13) 0.0019(10) 0.0030(10) 0.0007(10) C8 0.0251(11) 0.0238(13) 0.0217(11) 0.0007(10) 0.0007(9) -0.0024(9) C9 0.0302(12) 0.0247(13) 0.0299(15) -0.0032(11) -0.0046(10) -0.0014(10) C10 0.0275(12) 0.0252(14) 0.0296(13) -0.0003(12) -0.0087(10) -0.0026(11) C11 0.0417(15) 0.0224(15) 0.0316(15) 0.0011(13) -0.0074(12) -0.0046(11) C12 0.0477(16) 0.0445(18) 0.0300(14) 0.0042(15) -0.0002(14) -0.0104(15) C13 0.0451(17) 0.053(2) 0.0350(16) -0.0071(16) 0.0068(15) 0.0046(16) C14 0.0450(16) 0.0281(16) 0.0382(15) -0.0040(13) -0.0048(14) 0.0057(12) C15 0.0323(13) 0.0247(13) 0.0355(14) -0.0004(13) -0.0038(11) -0.0019(11) Cl1 0.0332(3) 0.0634(5) 0.0380(4) 0.0078(4) -0.0096(3) -0.0006(3) F1 0.0594(12) 0.0250(9) 0.0469(11) 0.0051(9) -0.0017(9) -0.0077(8) F2 0.0676(14) 0.0355(11) 0.0606(13) -0.0048(10) 0.0079(11) 0.0169(10) N1 0.0268(9) 0.0223(10) 0.0277(10) 0.0008(10) -0.0011(10) 0.0012(9) N2 0.0246(10) 0.0211(10) 0.0290(11) -0.0014(9) -0.0013(8) -0.0002(8) N3 0.0312(11) 0.0175(12) 0.0469(16) -0.0002(10) -0.0009(10) -0.0026(9) O1 0.0258(8) 0.0203(9) 0.0307(11) 0.0023(8) -0.0013(7) -0.0025(7) S1 0.0316(3) 0.0220(3) 0.0351(3) 0.0052(3) -0.0029(3) -0.0004(3) 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 1 0 0 0.0106 -1 0 0 0.0076 1 -1 0 0.0176 -1 1 0 0.0176 2 0 5 0.0692 -2 0 -5 0.0432 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 C6 121.9(3) . . ? C2 C1 Cl1 118.8(2) . . ? C6 C1 Cl1 119.4(2) . . ? C1 C2 H2 120.6 . . ? C3 C2 C1 118.9(3) . . ? C3 C2 H2 120.6 . . ? C2 C3 H3 120.0 . . ? C2 C3 C4 120.0(3) . . ? C4 C3 H3 120.0 . . ? C3 C4 C7 120.2(3) . . ? C5 C4 C3 120.4(3) . . ? C5 C4 C7 119.4(2) . . ? C4 C5 H5 120.1 . . ? C6 C5 C4 119.7(3) . . ? C6 C5 H5 120.1 . . ? C1 C6 C5 119.1(3) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? N1 C7 C4 128.7(3) . . ? N1 C7 O1 113.4(2) . . ? O1 C7 C4 117.9(2) . . ? N2 C8 O1 105.0(2) . . ? N2 C8 S1 131.2(2) . . ? O1 C8 S1 123.77(19) . . ? 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 112.6(2) . . ? C15 C10 C11 116.3(3) . . ? N3 C10 C11 118.9(3) . . ? N3 C10 C15 124.7(3) . . ? C12 C11 C10 124.4(3) . . ? C12 C11 F1 119.3(3) . . ? F1 C11 C10 116.4(3) . . ? C11 C12 H12 120.5 . . ? C11 C12 C13 119.0(3) . . ? C13 C12 H12 120.5 . . ? C12 C13 H13 121.5 . . ? C14 C13 C12 116.9(3) . . ? C14 C13 H13 121.5 . . ? C13 C14 C15 124.6(3) . . ? F2 C14 C13 118.1(3) . . ? F2 C14 C15 117.3(3) . . ? C10 C15 H15 120.6 . . ? C14 C15 C10 118.8(3) . . ? C14 C15 H15 120.6 . . ? C7 N1 N2 103.6(2) . . ? C8 N2 C9 128.1(2) . . ? C8 N2 N1 112.1(2) . . ? N1 N2 C9 119.8(2) . . ? C9 N3 H3A 115(2) . . ? C10 N3 C9 124.4(2) . . ? C10 N3 H3A 120(2) . . ? C8 O1 C7 105.9(2) . . ? 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 1.382(4) . ? C1 C6 1.383(4) . ? C1 Cl1 1.739(3) . ? C2 H2 0.9500 . ? C2 C3 1.381(4) . ? C3 H3 0.9500 . ? C3 C4 1.392(4) . ? C4 C5 1.390(4) . ? C4 C7 1.461(4) . ? C5 H5 0.9500 . ? C5 C6 1.383(4) . ? C6 H6 0.9500 . ? C7 N1 1.280(4) . ? C7 O1 1.374(3) . ? C8 N2 1.342(4) . ? C8 O1 1.371(3) . ? C8 S1 1.649(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C9 N2 1.467(3) . ? C9 N3 1.417(4) . ? C10 C11 1.394(4) . ? C10 C15 1.393(4) . ? C10 N3 1.379(4) . ? C11 C12 1.364(5) . ? C11 F1 1.367(4) . ? C12 H12 0.9500 . ? C12 C13 1.392(5) . ? C13 H13 0.9500 . ? C13 C14 1.371(5) . ? C14 C15 1.374(5) . ? C14 F2 1.369(4) . ? C15 H15 0.9500 . ? N1 N2 1.386(3) . ? N3 H3A 0.79(4) . ? 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 0.2(5) . . . . ? C2 C1 C6 C5 1.1(4) . . . . ? C2 C3 C4 C5 0.9(5) . . . . ? C2 C3 C4 C7 -176.8(3) . . . . ? C3 C4 C5 C6 -1.1(4) . . . . ? C3 C4 C7 N1 174.4(3) . . . . ? C3 C4 C7 O1 -3.6(4) . . . . ? C4 C5 C6 C1 0.0(4) . . . . ? C4 C7 N1 N2 -177.8(2) . . . . ? C4 C7 O1 C8 177.3(2) . . . . ? C5 C4 C7 N1 -3.3(4) . . . . ? C5 C4 C7 O1 178.7(2) . . . . ? C6 C1 C2 C3 -1.3(4) . . . . ? C7 C4 C5 C6 176.7(2) . . . . ? C7 N1 N2 C8 0.6(3) . . . . ? C7 N1 N2 C9 178.7(2) . . . . ? C10 C11 C12 C13 1.1(5) . . . . ? C11 C10 C15 C14 0.7(4) . . . . ? C11 C10 N3 C9 -174.4(3) . . . . ? C11 C12 C13 C14 -0.1(5) . . . . ? C12 C13 C14 C15 -0.6(6) . . . . ? C12 C13 C14 F2 178.8(3) . . . . ? C13 C14 C15 C10 0.2(5) . . . . ? C15 C10 C11 C12 -1.4(5) . . . . ? C15 C10 C11 F1 -179.6(3) . . . . ? C15 C10 N3 C9 5.0(5) . . . . ? Cl1 C1 C2 C3 178.7(2) . . . . ? Cl1 C1 C6 C5 -178.9(2) . . . . ? F1 C11 C12 C13 179.2(3) . . . . ? F2 C14 C15 C10 -179.2(3) . . . . ? N1 C7 O1 C8 -1.0(3) . . . . ? N2 C8 O1 C7 1.3(3) . . . . ? N2 C9 N3 C10 -87.3(3) . . . . ? N3 C9 N2 C8 114.8(3) . . . . ? N3 C9 N2 N1 -62.9(3) . . . . ? N3 C10 C11 C12 178.0(3) . . . . ? N3 C10 C11 F1 -0.2(4) . . . . ? N3 C10 C15 C14 -178.6(3) . . . . ? O1 C7 N1 N2 0.2(3) . . . . ? O1 C8 N2 C9 -179.1(2) . . . . ? O1 C8 N2 N1 -1.2(3) . . . . ? S1 C8 N2 C9 1.1(4) . . . . ? S1 C8 N2 N1 178.9(2) . . . . ? S1 C8 O1 C7 -178.86(19) . . . . ?