#------------------------------------------------------------------------------ #$Date: 2026-06-17 23:23:47 +0100 (Wed, 17 Jun 2026) $ #$Revision: 306587 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/74/1577409.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_1577409 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 'C13 H7 Cl F3 N O' _chemical_formula_sum 'C13 H7 Cl F3 N O' _chemical_formula_weight 285.65 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2025-07-24 _audit_creation_method ; Olex2 1.5 (compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308) ; _audit_update_record ; 2025-07-24 deposited with the CCDC. 2026-06-08 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 105.477(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.6528(4) _cell_length_b 7.5835(3) _cell_length_c 16.5958(6) _cell_measurement_reflns_used 3603 _cell_measurement_temperature 99.99(10) _cell_measurement_theta_max 77.3570 _cell_measurement_theta_min 4.7440 _cell_volume 1170.79(8) _computing_cell_refinement 'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)' _computing_data_collection 'CrysAlisPro system (CCD 44.117a 64-bit (release 07-07-2025))' _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 99.99(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.943 _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 -2.00 46.00 0.50 0.05 -- 46.62 -69.00 -32.00 96 2 \w 35.00 60.00 0.50 0.08 -- 107.75 -61.00-120.00 50 3 \w 41.00 82.00 0.50 0.08 -- 107.75 -69.00 -32.00 82 4 \w 36.00 62.00 0.50 0.08 -- 107.75 -61.00 30.00 52 5 \w 45.00 70.00 0.50 0.08 -- 107.75 -61.00 90.00 50 6 \w 39.00 67.00 0.50 0.08 -- 107.75 -61.00 120.00 56 7 \w 99.00 170.00 0.50 0.08 -- 107.75 45.00 30.00 142 8 \w 142.00 173.00 0.50 0.08 -- 107.75 45.00 0.00 62 9 \w 106.00 134.00 0.50 0.08 -- 107.75 45.00 0.00 56 10 \w 106.00 175.00 0.50 0.08 -- 107.75 69.00 99.00 138 11 \w 48.00 73.00 0.50 0.05 -- 46.62 69.00 99.00 50 12 \w -7.00 28.00 0.50 0.05 -- -46.62 19.00 90.00 70 13 \w -21.00 17.00 0.50 0.05 -- -46.62 69.00 99.00 76 14 \w -52.00 -26.00 0.50 0.05 -- -46.62 69.00 99.00 52 15 \w 36.00 99.00 0.50 0.08 -- 107.75 -95.00-120.00 126 16 \w -21.00 21.00 0.50 0.05 -- -46.62 19.00 -90.00 84 17 \w -22.00 4.00 0.50 0.05 -- -46.62 19.00-120.00 52 18 \w -70.00 -45.00 0.50 0.08 -- -109.00 61.00 -30.00 50 19 \w -67.00 -42.00 0.50 0.08 -- -109.00 61.00 -60.00 50 20 \w -78.00 -39.00 0.50 0.08 -- -109.00 69.00 99.00 78 21 \w -66.00 -41.00 0.50 0.08 -- -109.00 61.00 60.00 50 22 \w -164.00-139.00 0.50 0.08 -- -109.00 -45.00 -90.00 50 23 \w -173.00-133.00 0.50 0.08 -- -109.00 -69.00 -32.00 80 24 \w -121.00 -96.00 0.50 0.08 -- -109.00 -45.00 -90.00 50 25 \w -118.00 -28.00 0.50 0.05 -- -46.62 -69.00 -32.00 180 ; _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 -0.0890788000 _diffrn_orient_matrix_UB_12 0.1327210000 _diffrn_orient_matrix_UB_13 -0.0632603000 _diffrn_orient_matrix_UB_21 0.1397261000 _diffrn_orient_matrix_UB_22 0.0882182000 _diffrn_orient_matrix_UB_23 -0.0079995000 _diffrn_orient_matrix_UB_31 0.0035269000 _diffrn_orient_matrix_UB_32 -0.1258463000 _diffrn_orient_matrix_UB_33 -0.0721474000 _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 0.0414 _diffrn_reflns_av_unetI/netI 0.0490 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.943 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 6793 _diffrn_reflns_point_group_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.943 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 77.377 _diffrn_reflns_theta_min 4.754 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 3.206 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.740 _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 1.621 _exptl_crystal_description plate _exptl_crystal_F_000 576 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.084 _exptl_crystal_size_min 0.028 _refine_diff_density_max 0.261 _refine_diff_density_min -0.390 _refine_diff_density_rms 0.062 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 2353 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.057 _refine_ls_R_factor_all 0.0504 _refine_ls_R_factor_gt 0.0390 _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^)+(0.0339P)^2^+0.7786P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0922 _refine_ls_wR_factor_ref 0.0972 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1919 _reflns_number_total 2353 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc04438g2.cif _cod_data_source_block s6737r _cod_original_cell_volume 1170.80(7) _cod_database_code 1577409 _shelx_shelxl_version_number 2019/3 _chemical_oxdiff_formula C13H7ClF3NO _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 2.a Aromatic/amide H refined with riding coordinates: C9(H9), C1(H1), C3(H3), C13(H13), C10(H10), C11(H11), C12(H12) ; _shelx_res_file ; TITL s6737r_a.res in P2(1)/c s6737r.res created by SHELXL-2019/3 at 09:06:09 on 24-Jul-2025 REM Old TITL s6737r in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.113, Rweak 0.327, Alpha 0.025 REM 0.351 for 146 systematic absences, Orientation as input REM Formula found by SHELXT: C6 N O1 Cl CELL 1.54184 9.652797 7.583494 16.595829 90 105.4766 90 ZERR 4 0.000363 0.000267 0.000551 0 0.0037 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Cl F N O UNIT 52 28 4 12 4 4 L.S. 14 PLAN 1 TEMP -173 CONF BOND fmap 2 MORE -1 BOND $H ACTA REM REM REM WGHT 0.033900 0.778600 FVAR 5.73540 CL1 3 0.772675 0.443327 0.561722 11.00000 0.02463 0.02904 = 0.02507 0.00335 0.01073 -0.00211 F1 4 0.221265 0.086719 0.671145 11.00000 0.03080 0.03180 = 0.02251 -0.00137 0.01345 -0.00518 F3 4 0.218785 -0.043391 0.555638 11.00000 0.03588 0.02983 = 0.03349 -0.01320 0.01459 -0.01050 F2 4 0.117101 0.208826 0.553457 11.00000 0.02083 0.03995 = 0.03804 0.00786 0.00424 0.00085 O1 6 0.499604 0.277303 0.804046 11.00000 0.02856 0.04649 = 0.01549 0.00479 0.00531 0.01487 N1 5 0.408672 0.176470 0.521202 11.00000 0.02437 0.02337 = 0.01564 -0.00091 0.00674 0.00129 C8 1 0.290661 0.445151 0.744722 11.00000 0.01804 0.01984 = 0.01628 -0.00264 0.00482 -0.00206 C4 1 0.451619 0.306018 0.658390 11.00000 0.01971 0.01921 = 0.01636 0.00312 0.00573 0.00575 C9 1 0.249970 0.449165 0.819663 11.00000 0.02056 0.02206 = 0.01648 -0.00031 0.00347 -0.00068 AFIX 43 H9 2 0.301087 0.380960 0.866125 11.00000 -1.20000 AFIX 0 C5 1 0.371128 0.204783 0.592284 11.00000 0.02016 0.02033 = 0.01568 0.00117 0.00518 0.00350 C7 1 0.417147 0.337887 0.741590 11.00000 0.02247 0.02400 = 0.01510 -0.00085 0.00441 -0.00081 C1 1 0.529074 0.250936 0.512965 11.00000 0.02570 0.02121 = 0.01729 0.00193 0.00879 0.00301 AFIX 43 H1 2 0.555680 0.234481 0.462342 11.00000 -1.20000 AFIX 0 C3 1 0.579281 0.379230 0.649904 11.00000 0.02331 0.01761 = 0.01772 -0.00010 0.00378 0.00125 AFIX 43 H3 2 0.639316 0.446544 0.693836 11.00000 -1.20000 AFIX 0 C2 1 0.616703 0.351605 0.575883 11.00000 0.02343 0.01955 = 0.02027 0.00437 0.00855 0.00496 C13 1 0.215006 0.546130 0.676801 11.00000 0.02146 0.02264 = 0.01681 0.00034 0.00573 -0.00100 AFIX 43 H13 2 0.241849 0.543404 0.625751 11.00000 -1.20000 AFIX 0 C10 1 0.135226 0.552614 0.825899 11.00000 0.02240 0.02527 = 0.02264 -0.00460 0.01048 -0.00347 AFIX 43 H10 2 0.106960 0.554336 0.876514 11.00000 -1.20000 AFIX 0 C11 1 0.061227 0.653967 0.758378 11.00000 0.02074 0.02356 = 0.02872 -0.00106 0.00964 0.00077 AFIX 43 H11 2 -0.016682 0.726007 0.763195 11.00000 -1.20000 AFIX 0 C12 1 0.100826 0.650293 0.683804 11.00000 0.02054 0.02501 = 0.02515 0.00225 0.00574 0.00050 AFIX 43 H12 2 0.049625 0.719187 0.637621 11.00000 -1.20000 AFIX 0 C6 1 0.232183 0.113886 0.592888 11.00000 0.02558 0.02422 = 0.01815 -0.00153 0.00674 0.00012 HKLF 4 REM s6737r_a.res in P2(1)/c REM wR2 = 0.0972, GooF = S = 1.057, Restrained GooF = 1.057 for all data REM R1 = 0.0390 for 1919 Fo > 4sig(Fo) and 0.0504 for all 2353 data REM 172 parameters refined using 0 restraints END WGHT 0.0339 0.7766 REM Highest difference peak 0.261, deepest hole -0.390, 1-sigma level 0.062 Q1 1 0.7758 0.2700 0.5662 11.00000 0.05 0.26 ; _shelx_res_checksum 2768 _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 1.189 _oxdiff_exptl_absorpt_empirical_full_min 0.815 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 0.77268(6) 0.44333(7) 0.56172(3) 0.02546(15) Uani 1 1 d . . . . . F1 F 0.22126(14) 0.08672(18) 0.67115(7) 0.0272(3) Uani 1 1 d . . . . . F3 F 0.21879(15) -0.04339(18) 0.55564(8) 0.0320(3) Uani 1 1 d . . . . . F2 F 0.11710(14) 0.20883(19) 0.55346(8) 0.0336(3) Uani 1 1 d . . . . . O1 O 0.49960(17) 0.2773(2) 0.80405(9) 0.0303(4) Uani 1 1 d . . . . . N1 N 0.40867(19) 0.1765(2) 0.52120(10) 0.0209(4) Uani 1 1 d . . . . . C8 C 0.2907(2) 0.4452(3) 0.74472(12) 0.0180(4) Uani 1 1 d . . . . . C4 C 0.4516(2) 0.3060(3) 0.65839(12) 0.0183(4) Uani 1 1 d . . . . . C9 C 0.2500(2) 0.4492(3) 0.81966(12) 0.0200(4) Uani 1 1 d . . . . . H9 H 0.301087 0.380960 0.866125 0.024 Uiso 1 1 calc R U . . . C5 C 0.3711(2) 0.2048(3) 0.59228(12) 0.0186(4) Uani 1 1 d . . . . . C7 C 0.4171(2) 0.3379(3) 0.74159(12) 0.0206(4) Uani 1 1 d . . . . . C1 C 0.5291(2) 0.2509(3) 0.51297(12) 0.0208(4) Uani 1 1 d . . . . . H1 H 0.555680 0.234481 0.462342 0.025 Uiso 1 1 calc R U . . . C3 C 0.5793(2) 0.3792(3) 0.64990(12) 0.0199(4) Uani 1 1 d . . . . . H3 H 0.639316 0.446544 0.693836 0.024 Uiso 1 1 calc R U . . . C2 C 0.6167(2) 0.3516(3) 0.57588(12) 0.0206(4) Uani 1 1 d . . . . . C13 C 0.2150(2) 0.5461(3) 0.67680(12) 0.0202(4) Uani 1 1 d . . . . . H13 H 0.241849 0.543404 0.625751 0.024 Uiso 1 1 calc R U . . . C10 C 0.1352(2) 0.5526(3) 0.82590(13) 0.0226(4) Uani 1 1 d . . . . . H10 H 0.106960 0.554336 0.876514 0.027 Uiso 1 1 calc R U . . . C11 C 0.0612(2) 0.6540(3) 0.75838(13) 0.0238(5) Uani 1 1 d . . . . . H11 H -0.016682 0.726007 0.763195 0.029 Uiso 1 1 calc R U . . . C12 C 0.1008(2) 0.6503(3) 0.68380(13) 0.0236(5) Uani 1 1 d . . . . . H12 H 0.049625 0.719187 0.637621 0.028 Uiso 1 1 calc R U . . . C6 C 0.2322(2) 0.1139(3) 0.59289(13) 0.0225(5) 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 Cl1 0.0246(3) 0.0290(3) 0.0251(3) 0.0034(2) 0.01073(19) -0.0021(2) F1 0.0308(7) 0.0318(7) 0.0225(6) -0.0014(5) 0.0134(5) -0.0052(6) F3 0.0359(8) 0.0298(8) 0.0335(7) -0.0132(6) 0.0146(6) -0.0105(6) F2 0.0208(7) 0.0400(8) 0.0380(7) 0.0079(6) 0.0042(6) 0.0008(6) O1 0.0286(9) 0.0465(10) 0.0155(7) 0.0048(7) 0.0053(6) 0.0149(8) N1 0.0244(9) 0.0234(9) 0.0156(8) -0.0009(7) 0.0067(7) 0.0013(7) C8 0.0180(9) 0.0198(10) 0.0163(9) -0.0026(8) 0.0048(7) -0.0021(8) C4 0.0197(10) 0.0192(11) 0.0164(9) 0.0031(8) 0.0057(8) 0.0058(8) C9 0.0206(10) 0.0221(11) 0.0165(9) -0.0003(8) 0.0035(8) -0.0007(9) C5 0.0202(10) 0.0203(11) 0.0157(9) 0.0012(8) 0.0052(8) 0.0035(8) C7 0.0225(10) 0.0240(11) 0.0151(9) -0.0009(8) 0.0044(8) -0.0008(9) C1 0.0257(11) 0.0212(11) 0.0173(10) 0.0019(8) 0.0088(8) 0.0030(9) C3 0.0233(10) 0.0176(10) 0.0177(9) -0.0001(8) 0.0038(8) 0.0012(8) C2 0.0234(10) 0.0196(11) 0.0203(10) 0.0044(8) 0.0086(8) 0.0050(8) C13 0.0215(10) 0.0226(11) 0.0168(9) 0.0003(8) 0.0057(8) -0.0010(8) C10 0.0224(10) 0.0253(11) 0.0226(10) -0.0046(9) 0.0105(8) -0.0035(9) C11 0.0207(10) 0.0236(12) 0.0287(11) -0.0011(9) 0.0096(9) 0.0008(9) C12 0.0205(10) 0.0250(12) 0.0251(10) 0.0023(9) 0.0057(9) 0.0005(9) C6 0.0256(11) 0.0242(11) 0.0182(9) -0.0015(9) 0.0067(8) 0.0001(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' 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 -6 0 0 0.0193 6 0 -1 0.0070 1 -3 -8 0.0867 0 3 8 0.0612 2 1 -10 0.0478 -2 -1 11 0.0297 -1 -5 2 0.0539 0 5 1 0.0588 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 C5 118.08(18) . . ? C9 C8 C7 118.20(18) . . ? C13 C8 C9 119.63(19) . . ? C13 C8 C7 122.12(17) . . ? C5 C4 C7 126.17(19) . . ? C3 C4 C5 117.55(17) . . ? C3 C4 C7 116.21(18) . . ? C8 C9 H9 120.1 . . ? C10 C9 C8 119.90(19) . . ? C10 C9 H9 120.1 . . ? N1 C5 C4 123.79(19) . . ? N1 C5 C6 112.44(18) . . ? C4 C5 C6 123.76(17) . . ? O1 C7 C8 122.44(18) . . ? O1 C7 C4 117.45(19) . . ? C8 C7 C4 120.06(17) . . ? N1 C1 H1 119.0 . . ? N1 C1 C2 122.05(18) . . ? C2 C1 H1 119.0 . . ? C4 C3 H3 120.8 . . ? C2 C3 C4 118.45(19) . . ? C2 C3 H3 120.8 . . ? C1 C2 Cl1 119.85(15) . . ? C1 C2 C3 120.0(2) . . ? C3 C2 Cl1 120.11(17) . . ? C8 C13 H13 120.0 . . ? C12 C13 C8 120.07(18) . . ? C12 C13 H13 120.0 . . ? C9 C10 H10 119.9 . . ? C9 C10 C11 120.20(19) . . ? C11 C10 H10 119.9 . . ? C10 C11 H11 119.9 . . ? C10 C11 C12 120.2(2) . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 120.0(2) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? F1 C6 C5 111.99(17) . . ? F3 C6 F1 106.70(17) . . ? F3 C6 F2 106.81(17) . . ? F3 C6 C5 112.43(17) . . ? F2 C6 F1 106.58(17) . . ? F2 C6 C5 111.95(18) . . ? 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 C2 1.731(2) . ? F1 C6 1.347(2) . ? F3 C6 1.334(3) . ? F2 C6 1.339(3) . ? O1 C7 1.216(3) . ? N1 C5 1.341(2) . ? N1 C1 1.332(3) . ? C8 C9 1.401(3) . ? C8 C7 1.480(3) . ? C8 C13 1.397(3) . ? C4 C5 1.393(3) . ? C4 C7 1.523(3) . ? C4 C3 1.393(3) . ? C9 H9 0.9500 . ? C9 C10 1.384(3) . ? C5 C6 1.510(3) . ? C1 H1 0.9500 . ? C1 C2 1.385(3) . ? C3 H3 0.9500 . ? C3 C2 1.386(3) . ? C13 H13 0.9500 . ? C13 C12 1.386(3) . ? C10 H10 0.9500 . ? C10 C11 1.389(3) . ? C11 H11 0.9500 . ? C11 C12 1.390(3) . ? C12 H12 0.9500 . ? 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 N1 C5 C6 F1 157.25(18) . . . . ? N1 C5 C6 F3 37.1(2) . . . . ? N1 C5 C6 F2 -83.1(2) . . . . ? N1 C1 C2 Cl1 179.43(16) . . . . ? N1 C1 C2 C3 -0.8(3) . . . . ? C8 C9 C10 C11 -0.7(3) . . . . ? C8 C13 C12 C11 -0.2(3) . . . . ? C4 C5 C6 F1 -22.5(3) . . . . ? C4 C5 C6 F3 -142.6(2) . . . . ? C4 C5 C6 F2 97.2(2) . . . . ? C4 C3 C2 Cl1 178.82(16) . . . . ? C4 C3 C2 C1 -1.0(3) . . . . ? C9 C8 C7 O1 -12.1(3) . . . . ? C9 C8 C7 C4 170.42(19) . . . . ? C9 C8 C13 C12 0.3(3) . . . . ? C9 C10 C11 C12 0.8(3) . . . . ? C5 N1 C1 C2 1.6(3) . . . . ? C5 C4 C7 O1 114.0(2) . . . . ? C5 C4 C7 C8 -68.4(3) . . . . ? C5 C4 C3 C2 1.8(3) . . . . ? C7 C8 C9 C10 177.84(19) . . . . ? C7 C8 C13 C12 -177.3(2) . . . . ? C7 C4 C5 N1 -177.9(2) . . . . ? C7 C4 C5 C6 1.8(3) . . . . ? C7 C4 C3 C2 178.97(18) . . . . ? C1 N1 C5 C4 -0.7(3) . . . . ? C1 N1 C5 C6 179.56(18) . . . . ? C3 C4 C5 N1 -1.0(3) . . . . ? C3 C4 C5 C6 178.7(2) . . . . ? C3 C4 C7 O1 -62.9(3) . . . . ? C3 C4 C7 C8 114.7(2) . . . . ? C13 C8 C9 C10 0.1(3) . . . . ? C13 C8 C7 O1 165.5(2) . . . . ? C13 C8 C7 C4 -11.9(3) . . . . ? C10 C11 C12 C13 -0.4(3) . . . . ? 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 -6.0599 0.3269 0.2632 0.5665 -0.8200 -0.0815 6.0885 -0.4299 -0.5470 -0.5648 0.8172 0.1150 1.1321 -3.0700 -8.4316 0.0251 -0.0452 0.9987 -0.4533 3.0248 8.3781 -0.0882 0.1365 -0.9867 2.3778 1.0286 -10.4484 0.5857 0.5066 0.6328 -2.3731 -0.7924 10.5521 -0.5613 -0.4859 -0.6699 -0.9704 -4.8109 1.9377 -0.6747 -0.5755 0.4622 0.3751 4.8914 0.8570 0.5616 0.4771 -0.6761