#------------------------------------------------------------------------------ #$Date: 2026-06-17 23:23:47 +0100 (Wed, 17 Jun 2026) $ #$Revision: 306587 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/74/1577407.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_1577407 loop_ _publ_author_name 'Wang, Haiwen' 'Bhaduri, Nilanjan' 'Greaney, Michael F.' _publ_section_title ; Trifluoromethylation of pyridines through skeletal rearrangement ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D6SC04438G _journal_year 2026 _chemical_formula_moiety 'C14 H10 Cl F2 N O2' _chemical_formula_sum 'C14 H10 Cl F2 N O2' _chemical_formula_weight 297.68 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2025-11-10 _audit_creation_method ; Olex2 1.5 (compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314) ; _audit_update_record ; 2025-12-14 deposited with the CCDC. 2026-06-08 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 10.69639(17) _cell_length_b 11.34198(17) _cell_length_c 21.1345(3) _cell_measurement_reflns_used 6979 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 77.1500 _cell_measurement_theta_min 2.0990 _cell_volume 2564.00(7) _computing_cell_refinement 'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)' _computing_data_collection 'CrysAlisPro system (CCD 44.122a 64-bit (release 14-09-2025))' _computing_data_reduction 'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2019/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.00(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.962 _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 64.00 105.00 0.50 0.05 -- 107.75 -95.00-120.00 82 2 \w 46.00 75.00 0.50 0.05 -- 107.75-124.00 169.00 58 3 \w -21.00 24.00 0.50 0.05 -- -46.51 19.00-120.00 90 4 \w -9.00 29.00 0.50 0.05 -- -46.51 19.00 -90.00 76 5 \w -16.00 20.00 0.50 0.05 -- -46.51 19.00 0.00 72 6 \w -68.00 -42.00 0.50 0.05 -- -109.00 61.00-150.00 52 7 \w -71.00 -39.00 0.50 0.05 -- -109.00 61.00-180.00 64 8 \w -109.00 -83.00 0.50 0.05 -- -109.00 124.00-112.00 52 9 \w -102.00 -71.00 0.50 0.05 -- -46.51 148.00 52.00 62 10 \w -67.00 -41.00 0.50 0.05 -- -46.51 148.00 52.00 52 11 \w -64.00 -36.00 0.50 0.05 -- -109.00 124.00-112.00 56 12 \w -166.00-140.00 0.50 0.05 -- -109.00 -38.00 32.00 52 13 \w 35.00 65.00 0.50 0.05 -- 107.75 -61.00 -60.00 60 14 \w 37.00 72.00 0.50 0.05 -- 107.75 -61.00 30.00 70 15 \w 60.00 113.00 0.50 0.05 -- 107.75 -77.00 120.00 106 16 \w 97.00 175.00 0.50 0.05 -- 107.75 84.00 1.00 156 17 \w -18.00 24.00 0.50 0.05 -- 46.51 -19.00 -90.00 84 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'ROD, Synergy Custom DW system, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0654685000 _diffrn_orient_matrix_UB_12 -0.0220299000 _diffrn_orient_matrix_UB_13 0.0638436000 _diffrn_orient_matrix_UB_21 -0.1084094000 _diffrn_orient_matrix_UB_22 0.0617893000 _diffrn_orient_matrix_UB_23 0.0345991000 _diffrn_orient_matrix_UB_31 -0.0684724000 _diffrn_orient_matrix_UB_32 -0.1190202000 _diffrn_orient_matrix_UB_33 0.0062333000 _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 0.0241 _diffrn_reflns_av_unetI/netI 0.0224 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.962 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 9507 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.962 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 77.911 _diffrn_reflns_theta_min 4.184 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.896 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.608 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024) Numerical absorption correction based on gaussian integration over a multifaceted crystal model 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 1.542 _exptl_crystal_description block _exptl_crystal_F_000 1216 _exptl_crystal_size_max 0.245 _exptl_crystal_size_mid 0.147 _exptl_crystal_size_min 0.079 _refine_diff_density_max 0.360 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.051 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 182 _refine_ls_number_reflns 2640 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.085 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0296 _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^)+(0.0394P)^2^+0.9990P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0779 _refine_ls_wR_factor_ref 0.0799 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2375 _reflns_number_total 2640 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc04438g2.cif _cod_data_source_block s6782r _cod_database_code 1577407 _shelx_shelxl_version_number 2019/3 _chemical_oxdiff_formula C14H10ClF2NO2 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C13(H13), C9(H9), C12(H12), C10(H10), C4(H4), C3(H3), C5(H5) 2.b Idealised Me refined as rotating group: C14(H14A,H14B,H14C) ; _shelx_res_file ; TITL s6782r_a.res in Pbca s6782r.res created by SHELXL-2019/3 at 14:43:06 on 10-Nov-2025 REM Old TITL s6782r in Pbca REM SHELXT solution in Pbca: R1 0.127, Rweak 0.047, Alpha 0.024 REM 0.603 for 258 systematic absences, Orientation as input REM Formula found by SHELXT: C14 N O1 Cl CELL 1.54184 10.696389 11.341977 21.134528 90 90 90 ZERR 8 0.000173 0.000169 0.000347 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 UNIT 112 80 8 16 8 16 L.S. 14 PLAN 5 TEMP -173 CONF BOND fmap 2 MORE -1 BOND $H ACTA REM REM REM WGHT 0.039400 0.999000 FVAR 3.68575 CL1 3 0.568875 0.603311 0.677331 11.00000 0.02648 0.02124 = 0.03199 0.00020 -0.00627 -0.00781 F2 4 0.553071 0.487283 0.575345 11.00000 0.03889 0.02510 = 0.02777 -0.00071 0.01521 -0.00572 F1 4 0.397888 0.602933 0.594563 11.00000 0.02911 0.02251 = 0.03371 0.01219 -0.00751 -0.00145 O2 6 0.517607 0.042312 0.373752 11.00000 0.02171 0.02348 = 0.01602 -0.00416 -0.00013 0.00209 O1 6 0.652421 0.271276 0.639092 11.00000 0.01671 0.03571 = 0.02367 -0.00755 -0.00324 0.00096 N1 5 0.306879 0.462248 0.685934 11.00000 0.01908 0.01691 = 0.01802 -0.00108 -0.00166 0.00115 C13 1 0.642077 0.145441 0.522188 11.00000 0.01325 0.01871 = 0.02025 0.00171 0.00071 -0.00145 AFIX 43 H13 2 0.718188 0.139622 0.545142 11.00000 -1.20000 AFIX 0 C11 1 0.519772 0.100977 0.429824 11.00000 0.02112 0.01474 = 0.01327 0.00078 0.00283 -0.00185 C1 1 0.404613 0.425219 0.651777 11.00000 0.01673 0.01703 = 0.01411 -0.00027 -0.00305 -0.00086 C9 1 0.430918 0.216844 0.513133 11.00000 0.01608 0.01698 = 0.02005 -0.00043 0.00076 0.00283 AFIX 43 H9 2 0.362168 0.259096 0.530328 11.00000 -1.20000 AFIX 0 C12 1 0.631445 0.091995 0.463927 11.00000 0.01548 0.01782 = 0.02003 -0.00019 0.00420 0.00057 AFIX 43 H12 2 0.699895 0.049062 0.446912 11.00000 -1.20000 AFIX 0 C10 1 0.419370 0.164884 0.454038 11.00000 0.01767 0.01852 = 0.01820 0.00016 -0.00243 0.00193 AFIX 43 H10 2 0.344227 0.172735 0.430450 11.00000 -1.20000 AFIX 0 C4 1 0.254287 0.259612 0.704687 11.00000 0.01705 0.01992 = 0.01845 0.00141 0.00032 -0.00246 AFIX 43 H4 2 0.199424 0.203764 0.723429 11.00000 -1.20000 AFIX 0 C2 1 0.435916 0.307066 0.642749 11.00000 0.01617 0.01709 = 0.01276 -0.00099 -0.00261 -0.00072 C8 1 0.541393 0.208324 0.547818 11.00000 0.01641 0.01447 = 0.01659 0.00108 0.00062 -0.00093 C7 1 0.553675 0.263936 0.610559 11.00000 0.01616 0.01646 = 0.01861 0.00110 -0.00004 -0.00017 C3 1 0.355458 0.223168 0.669088 11.00000 0.01966 0.01441 = 0.01926 -0.00071 -0.00139 0.00017 AFIX 43 H3 2 0.370316 0.141499 0.662527 11.00000 -1.20000 AFIX 0 C5 1 0.234612 0.379825 0.712452 11.00000 0.01593 0.02239 = 0.01709 -0.00242 -0.00028 0.00130 AFIX 43 H5 2 0.166318 0.404686 0.737905 11.00000 -1.20000 AFIX 0 C6 1 0.476436 0.525325 0.621491 11.00000 0.02107 0.01832 = 0.02032 -0.00031 -0.00014 -0.00012 C14 1 0.404927 0.046727 0.337459 11.00000 0.02939 0.02530 = 0.01945 -0.00364 -0.00597 0.00484 AFIX 137 H14A 2 0.415756 0.001160 0.298445 11.00000 -1.50000 H14B 2 0.385679 0.128852 0.326837 11.00000 -1.50000 H14C 2 0.336099 0.013195 0.362215 11.00000 -1.50000 AFIX 0 HKLF 4 REM s6782r_a.res in Pbca REM wR2 = 0.0799, GooF = S = 1.085, Restrained GooF = 1.085 for all data REM R1 = 0.0296 for 2375 Fo > 4sig(Fo) and 0.0334 for all 2640 data REM 182 parameters refined using 0 restraints END WGHT 0.0394 0.9991 REM Highest difference peak 0.360, deepest hole -0.260, 1-sigma level 0.051 Q1 1 0.5435 0.2244 0.5783 11.00000 0.05 0.36 Q2 1 0.4368 0.4632 0.6347 11.00000 0.05 0.29 Q3 1 0.4200 0.3679 0.6375 11.00000 0.05 0.27 Q4 1 0.4891 0.2163 0.5310 11.00000 0.05 0.26 Q5 1 0.2262 0.3228 0.6996 11.00000 0.05 0.26 ; _shelx_res_checksum 14501 _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 1.250 _oxdiff_exptl_absorpt_empirical_full_min 0.861 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' '-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 Cl1 Cl 0.56887(3) 0.60331(3) 0.67733(2) 0.02657(11) Uani 1 1 d . . . . . F2 F 0.55307(9) 0.48728(7) 0.57534(4) 0.0306(2) Uani 1 1 d . . . . . F1 F 0.39789(8) 0.60293(7) 0.59456(4) 0.0284(2) Uani 1 1 d . . . . . O2 O 0.51761(9) 0.04231(8) 0.37375(4) 0.0204(2) Uani 1 1 d . . . . . O1 O 0.65242(9) 0.27128(9) 0.63909(5) 0.0254(2) Uani 1 1 d . . . . . N1 N 0.30688(11) 0.46225(10) 0.68593(5) 0.0180(2) Uani 1 1 d . . . . . C13 C 0.64208(12) 0.14544(11) 0.52219(6) 0.0174(3) Uani 1 1 d . . . . . H13 H 0.718188 0.139622 0.545142 0.021 Uiso 1 1 calc R U . . . C11 C 0.51977(13) 0.10098(11) 0.42982(6) 0.0164(3) Uani 1 1 d . . . . . C1 C 0.40461(12) 0.42522(11) 0.65178(6) 0.0160(3) Uani 1 1 d . . . . . C9 C 0.43092(12) 0.21684(12) 0.51313(6) 0.0177(3) Uani 1 1 d . . . . . H9 H 0.362168 0.259096 0.530328 0.021 Uiso 1 1 calc R U . . . C12 C 0.63144(12) 0.09199(11) 0.46393(6) 0.0178(3) Uani 1 1 d . . . . . H12 H 0.699895 0.049062 0.446912 0.021 Uiso 1 1 calc R U . . . C10 C 0.41937(12) 0.16488(11) 0.45404(6) 0.0181(3) Uani 1 1 d . . . . . H10 H 0.344227 0.172735 0.430450 0.022 Uiso 1 1 calc R U . . . C4 C 0.25429(13) 0.25961(12) 0.70469(6) 0.0185(3) Uani 1 1 d . . . . . H4 H 0.199424 0.203764 0.723429 0.022 Uiso 1 1 calc R U . . . C2 C 0.43592(12) 0.30707(11) 0.64275(6) 0.0153(3) Uani 1 1 d . . . . . C8 C 0.54139(12) 0.20832(11) 0.54782(6) 0.0158(3) Uani 1 1 d . . . . . C7 C 0.55368(12) 0.26394(11) 0.61056(6) 0.0171(3) Uani 1 1 d . . . . . C3 C 0.35546(13) 0.22317(11) 0.66909(6) 0.0178(3) Uani 1 1 d . . . . . H3 H 0.370316 0.141499 0.662527 0.021 Uiso 1 1 calc R U . . . C5 C 0.23461(13) 0.37982(12) 0.71245(6) 0.0185(3) Uani 1 1 d . . . . . H5 H 0.166318 0.404686 0.737905 0.022 Uiso 1 1 calc R U . . . C6 C 0.47644(13) 0.52533(12) 0.62149(6) 0.0199(3) Uani 1 1 d . . . . . C14 C 0.40493(14) 0.04673(13) 0.33746(7) 0.0247(3) Uani 1 1 d . . . . . H14A H 0.415756 0.001160 0.298445 0.037 Uiso 1 1 calc R U . . . H14B H 0.385679 0.128852 0.326837 0.037 Uiso 1 1 calc R U . . . H14C H 0.336099 0.013195 0.362215 0.037 Uiso 1 1 calc R U . . . 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 0.0265(2) 0.02124(18) 0.0320(2) 0.00020(13) -0.00627(14) -0.00781(13) F2 0.0389(5) 0.0251(4) 0.0278(5) -0.0007(4) 0.0152(4) -0.0057(4) F1 0.0291(5) 0.0225(4) 0.0337(5) 0.0122(4) -0.0075(4) -0.0015(3) O2 0.0217(5) 0.0235(5) 0.0160(5) -0.0042(4) -0.0001(4) 0.0021(4) O1 0.0167(5) 0.0357(6) 0.0237(5) -0.0075(4) -0.0032(4) 0.0010(4) N1 0.0191(6) 0.0169(5) 0.0180(5) -0.0011(4) -0.0017(4) 0.0011(4) C13 0.0132(6) 0.0187(6) 0.0203(6) 0.0017(5) 0.0007(5) -0.0014(5) C11 0.0211(7) 0.0147(6) 0.0133(6) 0.0008(5) 0.0028(5) -0.0018(5) C1 0.0167(6) 0.0170(6) 0.0141(6) -0.0003(5) -0.0030(5) -0.0009(5) C9 0.0161(6) 0.0170(6) 0.0200(6) -0.0004(5) 0.0008(5) 0.0028(5) C12 0.0155(6) 0.0178(6) 0.0200(6) -0.0002(5) 0.0042(5) 0.0006(5) C10 0.0177(6) 0.0185(6) 0.0182(6) 0.0002(5) -0.0024(5) 0.0019(5) C4 0.0170(6) 0.0199(6) 0.0185(6) 0.0014(5) 0.0003(5) -0.0025(5) C2 0.0162(6) 0.0171(6) 0.0128(6) -0.0010(5) -0.0026(5) -0.0007(5) C8 0.0164(6) 0.0145(6) 0.0166(6) 0.0011(5) 0.0006(5) -0.0009(5) C7 0.0162(6) 0.0165(6) 0.0186(6) 0.0011(5) 0.0000(5) -0.0002(5) C3 0.0197(6) 0.0144(6) 0.0193(6) -0.0007(5) -0.0014(5) 0.0002(5) C5 0.0159(6) 0.0224(6) 0.0171(6) -0.0024(5) -0.0003(5) 0.0013(5) C6 0.0211(7) 0.0183(6) 0.0203(7) -0.0003(5) -0.0001(5) -0.0001(5) C14 0.0294(8) 0.0253(7) 0.0195(7) -0.0036(6) -0.0060(6) 0.0048(6) 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' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -3 -7 2 0.1309 -2 1 -2 0.0512 1 -1 2 0.0468 -1 -2 1 0.1300 1 2 0 0.1025 0 0 1 0.0517 0 0 -1 0.0272 2 1 -2 0.0891 3 -6 -7 0.0790 -5 0 10 0.0979 -3 6 7 0.1318 6 -3 -6 0.0552 5 0 10 0.0672 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O2 C14 117.71(11) . . ? C5 N1 C1 117.30(11) . . ? C12 C13 H13 119.8 . . ? C12 C13 C8 120.43(12) . . ? C8 C13 H13 119.8 . . ? O2 C11 C12 115.35(11) . . ? O2 C11 C10 124.18(12) . . ? C10 C11 C12 120.46(12) . . ? N1 C1 C2 124.27(12) . . ? N1 C1 C6 112.92(11) . . ? C2 C1 C6 122.78(12) . . ? C10 C9 H9 119.3 . . ? C10 C9 C8 121.32(12) . . ? C8 C9 H9 119.3 . . ? C13 C12 C11 119.94(12) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C11 C10 H10 120.5 . . ? C9 C10 C11 118.91(12) . . ? C9 C10 H10 120.5 . . ? C3 C4 H4 120.8 . . ? C3 C4 C5 118.47(12) . . ? C5 C4 H4 120.8 . . ? C1 C2 C7 124.90(12) . . ? C1 C2 C3 116.85(12) . . ? C3 C2 C7 118.12(11) . . ? C13 C8 C7 119.81(12) . . ? C9 C8 C13 118.93(12) . . ? C9 C8 C7 121.26(12) . . ? O1 C7 C2 118.48(12) . . ? O1 C7 C8 123.46(12) . . ? C8 C7 C2 117.95(11) . . ? C4 C3 C2 119.69(12) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? N1 C5 C4 123.33(12) . . ? N1 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? F2 C6 Cl1 107.60(9) . . ? F2 C6 C1 112.05(11) . . ? F1 C6 Cl1 107.66(9) . . ? F1 C6 F2 106.51(11) . . ? F1 C6 C1 110.69(11) . . ? C1 C6 Cl1 112.05(9) . . ? O2 C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? O2 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 Cl1 C6 1.7756(14) . ? F2 C6 1.3451(16) . ? F1 C6 1.3433(16) . ? O2 C11 1.3593(15) . ? O2 C14 1.4295(17) . ? O1 C7 1.2191(16) . ? N1 C1 1.3381(17) . ? N1 C5 1.3362(18) . ? C13 H13 0.9500 . ? C13 C12 1.3771(19) . ? C13 C8 1.4007(18) . ? C11 C12 1.3988(19) . ? C11 C10 1.3931(18) . ? C1 C2 1.3944(18) . ? C1 C6 1.5129(18) . ? C9 H9 0.9500 . ? C9 C10 1.3865(19) . ? C9 C8 1.3939(18) . ? C12 H12 0.9500 . ? C10 H10 0.9500 . ? C4 H4 0.9500 . ? C4 C3 1.3813(19) . ? C4 C5 1.3893(18) . ? C2 C7 1.5128(18) . ? C2 C3 1.3986(18) . ? C8 C7 1.4742(18) . ? C3 H3 0.9500 . ? C5 H5 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C11 C12 C13 -178.17(12) . . . . ? O2 C11 C10 C9 177.22(12) . . . . ? N1 C1 C2 C7 -172.81(12) . . . . ? N1 C1 C2 C3 3.05(19) . . . . ? N1 C1 C6 Cl1 74.64(13) . . . . ? N1 C1 C6 F2 -164.29(11) . . . . ? N1 C1 C6 F1 -45.55(15) . . . . ? C13 C8 C7 O1 9.4(2) . . . . ? C13 C8 C7 C2 -166.64(12) . . . . ? C1 N1 C5 C4 -1.87(19) . . . . ? C1 C2 C7 O1 74.05(18) . . . . ? C1 C2 C7 C8 -109.74(14) . . . . ? C1 C2 C3 C4 -3.10(18) . . . . ? C9 C8 C7 O1 -170.69(13) . . . . ? C9 C8 C7 C2 13.30(18) . . . . ? C12 C13 C8 C9 -0.63(19) . . . . ? C12 C13 C8 C7 179.31(12) . . . . ? C12 C11 C10 C9 -1.61(19) . . . . ? C10 C11 C12 C13 0.75(19) . . . . ? C10 C9 C8 C13 -0.3(2) . . . . ? C10 C9 C8 C7 179.80(12) . . . . ? C2 C1 C6 Cl1 -107.38(13) . . . . ? C2 C1 C6 F2 13.69(18) . . . . ? C2 C1 C6 F1 132.43(13) . . . . ? C8 C13 C12 C11 0.39(19) . . . . ? C8 C9 C10 C11 1.4(2) . . . . ? C7 C2 C3 C4 173.05(12) . . . . ? C3 C4 C5 N1 1.7(2) . . . . ? C3 C2 C7 O1 -101.76(15) . . . . ? C3 C2 C7 C8 74.45(16) . . . . ? C5 N1 C1 C2 -0.60(19) . . . . ? C5 N1 C1 C6 177.35(11) . . . . ? C5 C4 C3 C2 0.9(2) . . . . ? C6 C1 C2 C7 9.4(2) . . . . ? C6 C1 C2 C3 -174.70(12) . . . . ? C14 O2 C11 C12 178.89(11) . . . . ? C14 O2 C11 C10 0.01(18) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -2.5119 -6.7501 2.2587 0.1285 -0.0666 0.9895 -2.0000 1.0000 -2.0000 -0.2807 0.2094 0.0055 1.0000 -1.0000 2.0000 0.2152 -0.1010 0.0630 -1.0000 -2.0000 1.0000 0.0424 0.0194 0.3127 1.0000 2.0000 -0.0000 0.0214 0.0152 -0.3065 -0.0000 -0.0000 1.0000 0.0638 0.0346 0.0062 0.0000 0.0000 -1.0000 -0.0638 -0.0346 -0.0062 2.0000 1.0000 -2.0000 -0.0188 -0.2242 -0.2684 3.0000 -6.0000 -7.0000 -0.1183 -0.9382 0.4651 -5.0000 0.0000 10.0000 0.3111 0.8880 0.4047 -3.0000 6.0000 7.0000 0.1183 0.9382 -0.4651 6.0000 -3.0000 -6.0000 0.0758 -1.0434 -0.0912 5.0000 -0.0000 10.0000 0.9658 -0.1961 -0.2800