#------------------------------------------------------------------------------ #$Date: 2026-06-17 23:23:47 +0100 (Wed, 17 Jun 2026) $ #$Revision: 306587 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/74/1577403.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_1577403 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 Br F3 N O' _chemical_formula_sum 'C13 H7 Br F3 N O' _chemical_formula_weight 330.11 _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 2025-07-23 _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 105.133(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.7276(3) _cell_length_b 7.63087(19) _cell_length_c 16.6784(5) _cell_measurement_reflns_used 3864 _cell_measurement_temperature 99.97(10) _cell_measurement_theta_max 74.7560 _cell_measurement_theta_min 4.7020 _cell_volume 1195.11(6) _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 99.97(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.947 _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 -120.00 -41.00 0.50 0.05 -- -46.62 -22.00 -63.00 158 2 \w -172.00-102.00 0.50 0.07 -- -109.00 -15.00 0.00 140 3 \w -126.00-101.00 0.50 0.07 -- -109.00 -22.00 -63.00 50 4 \w -26.00 11.00 0.50 0.05 -- -46.62 38.00-120.00 74 5 \w -79.00 -54.00 0.50 0.07 -- -109.00 125.00-150.00 50 6 \w -112.00 -86.00 0.50 0.07 -- -109.00 125.00-150.00 52 7 \w -64.00 -39.00 0.50 0.07 -- -109.00 61.00 -30.00 50 8 \w -22.00 3.00 0.50 0.05 -- -46.62 22.00 102.00 50 9 \w 46.00 71.00 0.50 0.05 -- 46.62 22.00 102.00 50 10 \w 72.00 120.00 0.50 0.05 -- 46.62 22.00 102.00 96 11 \w 91.00 175.00 0.50 0.07 -- 107.75 61.00 30.00 168 12 \w 101.00 169.00 0.50 0.07 -- 107.75 22.00 102.00 136 13 \w 59.00 108.00 0.50 0.07 -- 107.75 -77.00 120.00 98 14 \w 36.00 69.00 0.50 0.07 -- 107.75 -61.00 90.00 66 15 \w 39.00 69.00 0.50 0.07 -- 107.75 -61.00 30.00 60 16 \w 44.00 70.00 0.50 0.07 -- 107.75 -61.00 150.00 52 17 \w 44.00 70.00 0.50 0.07 -- 107.75 -61.00 -30.00 52 18 \w 46.00 71.00 0.50 0.07 -- 107.75 -61.00 -60.00 50 19 \w 36.00 70.00 0.50 0.07 -- 107.75 -61.00 -90.00 68 20 \w 46.00 72.00 0.50 0.07 -- 107.75 -61.00-150.00 52 21 \w 36.00 72.00 0.50 0.07 -- 107.75 -61.00-180.00 72 22 \w -4.00 43.00 0.50 0.05 -- 46.62 -38.00-180.00 94 23 \w -25.00 0.00 0.50 0.05 -- 46.62 -22.00 -63.00 50 24 \w -28.00 20.00 0.50 0.05 -- 46.62 -19.00 150.00 96 ; _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 0.0211265000 _diffrn_orient_matrix_UB_12 0.0550671000 _diffrn_orient_matrix_UB_13 0.0912763000 _diffrn_orient_matrix_UB_21 -0.1624163000 _diffrn_orient_matrix_UB_22 0.0189731000 _diffrn_orient_matrix_UB_23 -0.0148528000 _diffrn_orient_matrix_UB_31 -0.0102558000 _diffrn_orient_matrix_UB_32 -0.1932093000 _diffrn_orient_matrix_UB_33 0.0245666000 _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 0.0493 _diffrn_reflns_av_unetI/netI 0.0529 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.947 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 6849 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.947 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 78.071 _diffrn_reflns_theta_min 4.709 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 5.002 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.571 _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 1.835 _exptl_crystal_description plate _exptl_crystal_F_000 648 _exptl_crystal_size_max 0.214 _exptl_crystal_size_mid 0.061 _exptl_crystal_size_min 0.026 _refine_diff_density_max 0.891 _refine_diff_density_min -1.265 _refine_diff_density_rms 0.112 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 2423 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.081 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0430 _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^)+(0.0651P)^2^+0.9228P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1153 _refine_ls_wR_factor_ref 0.1198 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2057 _reflns_number_total 2423 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc04438g2.cif _cod_data_source_block s6736r _cod_original_cell_volume 1195.10(6) _cod_database_code 1577403 _shelx_shelxl_version_number 2019/3 _chemical_oxdiff_formula C13H7BrF3NO _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), C3(H3), C13(H13), C10(H10), C1(H1), C12(H12), C11(H11) ; _shelx_res_file ; TITL s6736r_a.res in P2(1)/c s6736r.res created by SHELXL-2019/3 at 12:26:15 on 23-Jul-2025 REM Old TITL s6736r in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.099, Rweak 0.086, Alpha 0.019 REM 0.429 for 191 systematic absences, Orientation as input REM Formula found by SHELXT: C11 N O1 Br CELL 1.54184 9.727593 7.630868 16.678434 90 105.1335 90 ZERR 4 0.000267 0.00019 0.000452 0 0.0028 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Br 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 0.065100 0.922800 FVAR 4.38279 BR1 3 0.781345 0.554091 0.562131 11.00000 0.03057 0.03190 = 0.02491 -0.00298 0.01148 0.00207 F2 4 0.221768 0.920782 0.673435 11.00000 0.03838 0.03852 = 0.02140 -0.00042 0.01407 0.00451 F1 4 0.219204 1.049071 0.558470 11.00000 0.04445 0.03416 = 0.03414 0.01268 0.01736 0.01093 F3 4 0.119250 0.798427 0.556884 11.00000 0.02931 0.04476 = 0.03860 -0.00783 0.00633 0.00007 O1 6 0.496266 0.734961 0.805397 11.00000 0.03629 0.04886 = 0.01734 -0.00596 0.00780 -0.01465 N1 5 0.407676 0.829920 0.523868 11.00000 0.02941 0.02764 = 0.01591 0.00011 0.00752 -0.00192 C2 1 0.612956 0.655190 0.578070 11.00000 0.02754 0.02363 = 0.01981 -0.00484 0.00965 -0.00075 C9 1 0.220668 0.460324 0.680504 11.00000 0.03070 0.02532 = 0.02036 0.00101 0.00867 0.00330 AFIX 43 H9 2 0.249649 0.460788 0.630344 11.00000 -1.20000 AFIX 0 C8 1 0.291187 0.565385 0.746657 11.00000 0.02937 0.02540 = 0.01593 0.00009 0.00872 0.00228 C3 1 0.577147 0.631673 0.652031 11.00000 0.03096 0.02190 = 0.01779 0.00163 0.00504 -0.00309 AFIX 43 H3 2 0.637783 0.567603 0.696187 11.00000 -1.20000 AFIX 0 C4 1 0.450754 0.703451 0.660710 11.00000 0.02736 0.02460 = 0.01655 -0.00207 0.00733 -0.00304 C13 1 0.248401 0.563813 0.821440 11.00000 0.03003 0.03077 = 0.01492 0.00119 0.00947 0.00261 AFIX 43 H13 2 0.296674 0.634202 0.867113 11.00000 -1.20000 AFIX 0 C10 1 0.108528 0.355194 0.687473 11.00000 0.02833 0.02713 = 0.02548 -0.00126 0.00620 0.00078 AFIX 43 H10 2 0.060813 0.283414 0.642206 11.00000 -1.20000 AFIX 0 C1 1 0.526249 0.754161 0.515090 11.00000 0.03442 0.02997 = 0.01780 -0.00061 0.01033 -0.00487 AFIX 43 H1 2 0.552093 0.768313 0.464337 11.00000 -1.20000 AFIX 0 C7 1 0.415140 0.673392 0.743373 11.00000 0.03092 0.02588 = 0.01878 -0.00042 0.01073 -0.00115 C6 1 0.233146 0.893332 0.595490 11.00000 0.03152 0.02954 = 0.01956 0.00297 0.00738 -0.00084 C5 1 0.370810 0.803854 0.594933 11.00000 0.02917 0.02511 = 0.01613 -0.00169 0.00787 -0.00489 C12 1 0.135798 0.459004 0.827448 11.00000 0.03441 0.02993 = 0.02288 0.00634 0.01142 0.00565 AFIX 43 H12 2 0.106017 0.458109 0.877348 11.00000 -1.20000 AFIX 0 C11 1 0.065601 0.354581 0.760807 11.00000 0.02811 0.02849 = 0.02893 0.00291 0.01075 -0.00239 AFIX 43 H11 2 -0.011749 0.282784 0.765424 11.00000 -1.20000 AFIX 0 HKLF 4 REM s6736r_a.res in P2(1)/c REM wR2 = 0.1198, GooF = S = 1.081, Restrained GooF = 1.081 for all data REM R1 = 0.0430 for 2057 Fo > 4sig(Fo) and 0.0505 for all 2423 data REM 172 parameters refined using 0 restraints END WGHT 0.0651 0.9228 REM Highest difference peak 0.891, deepest hole -1.265, 1-sigma level 0.112 Q1 1 0.7170 0.4550 0.5520 11.00000 0.05 0.89 ; _shelx_res_checksum 52381 _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 1.619 _oxdiff_exptl_absorpt_empirical_full_min 0.748 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 Br1 Br 0.78135(4) 0.55409(5) 0.56213(2) 0.02834(17) Uani 1 1 d . . . . . F2 F 0.2218(2) 0.9208(3) 0.67344(13) 0.0316(5) Uani 1 1 d . . . . . F1 F 0.2192(3) 1.0491(3) 0.55847(14) 0.0363(6) Uani 1 1 d . . . . . F3 F 0.1192(2) 0.7984(3) 0.55688(14) 0.0380(5) Uani 1 1 d . . . . . O1 O 0.4963(3) 0.7350(4) 0.80540(15) 0.0340(6) Uani 1 1 d . . . . . N1 N 0.4077(3) 0.8299(4) 0.52387(16) 0.0240(6) Uani 1 1 d . . . . . C2 C 0.6130(4) 0.6552(5) 0.5781(2) 0.0230(7) Uani 1 1 d . . . . . C9 C 0.2207(4) 0.4603(4) 0.6805(2) 0.0251(7) Uani 1 1 d . . . . . H9 H 0.249649 0.460788 0.630344 0.030 Uiso 1 1 calc R U . . . C8 C 0.2912(4) 0.5654(4) 0.7467(2) 0.0230(7) Uani 1 1 d . . . . . C3 C 0.5771(4) 0.6317(4) 0.6520(2) 0.0238(7) Uani 1 1 d . . . . . H3 H 0.637783 0.567603 0.696187 0.029 Uiso 1 1 calc R U . . . C4 C 0.4508(4) 0.7035(4) 0.66071(19) 0.0225(7) Uani 1 1 d . . . . . C13 C 0.2484(4) 0.5638(5) 0.8214(2) 0.0246(7) Uani 1 1 d . . . . . H13 H 0.296674 0.634202 0.867113 0.029 Uiso 1 1 calc R U . . . C10 C 0.1085(4) 0.3552(5) 0.6875(2) 0.0271(7) Uani 1 1 d . . . . . H10 H 0.060813 0.283414 0.642206 0.033 Uiso 1 1 calc R U . . . C1 C 0.5262(4) 0.7542(5) 0.5151(2) 0.0267(7) Uani 1 1 d . . . . . H1 H 0.552093 0.768313 0.464337 0.032 Uiso 1 1 calc R U . . . C7 C 0.4151(4) 0.6734(5) 0.7434(2) 0.0244(7) Uani 1 1 d . . . . . C6 C 0.2331(4) 0.8933(5) 0.5955(2) 0.0267(7) Uani 1 1 d . . . . . C5 C 0.3708(4) 0.8039(4) 0.5949(2) 0.0231(7) Uani 1 1 d . . . . . C12 C 0.1358(4) 0.4590(5) 0.8274(2) 0.0283(8) Uani 1 1 d . . . . . H12 H 0.106017 0.458109 0.877348 0.034 Uiso 1 1 calc R U . . . C11 C 0.0656(4) 0.3546(5) 0.7608(2) 0.0279(8) Uani 1 1 d . . . . . H11 H -0.011749 0.282784 0.765424 0.033 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 Br1 0.0306(2) 0.0319(3) 0.0249(2) -0.00298(14) 0.01148(16) 0.00207(16) F2 0.0384(12) 0.0385(12) 0.0214(10) -0.0004(9) 0.0141(9) 0.0045(10) F1 0.0444(14) 0.0342(13) 0.0341(12) 0.0127(9) 0.0174(10) 0.0109(10) F3 0.0293(11) 0.0448(13) 0.0386(12) -0.0078(11) 0.0063(9) 0.0001(10) O1 0.0363(14) 0.0489(16) 0.0173(12) -0.0060(11) 0.0078(10) -0.0146(13) N1 0.0294(14) 0.0276(15) 0.0159(13) 0.0001(12) 0.0075(11) -0.0019(13) C2 0.0275(16) 0.0236(16) 0.0198(15) -0.0048(13) 0.0096(13) -0.0008(14) C9 0.0307(18) 0.0253(18) 0.0204(16) 0.0010(13) 0.0087(14) 0.0033(15) C8 0.0294(17) 0.0254(17) 0.0159(15) 0.0001(13) 0.0087(13) 0.0023(14) C3 0.0310(17) 0.0219(16) 0.0178(15) 0.0016(13) 0.0050(13) -0.0031(14) C4 0.0274(16) 0.0246(17) 0.0165(15) -0.0021(13) 0.0073(12) -0.0030(14) C13 0.0300(17) 0.0308(18) 0.0149(15) 0.0012(13) 0.0095(13) 0.0026(15) C10 0.0283(17) 0.0271(18) 0.0255(17) -0.0013(14) 0.0062(13) 0.0008(15) C1 0.0344(18) 0.0300(18) 0.0178(15) -0.0006(14) 0.0103(14) -0.0049(16) C7 0.0309(17) 0.0259(17) 0.0188(16) -0.0004(14) 0.0107(13) -0.0012(15) C6 0.0315(18) 0.0295(18) 0.0196(16) 0.0030(14) 0.0074(14) -0.0008(15) C5 0.0292(16) 0.0251(17) 0.0161(14) -0.0017(13) 0.0079(12) -0.0049(14) C12 0.0344(19) 0.0299(19) 0.0229(17) 0.0063(14) 0.0114(14) 0.0056(15) C11 0.0281(17) 0.0285(19) 0.0289(18) 0.0029(15) 0.0108(14) -0.0024(15) 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' Br Br -0.6763 1.2805 '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 -1 0.0175 6 0 1 0.0085 1 5 -3 0.0787 2 0 -11 0.0307 -2 0 11 0.0307 -1 -4 5 0.0891 3 0 7 0.0178 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 118.2(3) . . ? C3 C2 Br1 120.2(3) . . ? C3 C2 C1 120.2(3) . . ? C1 C2 Br1 119.6(3) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C10 C9 C8 120.3(3) . . ? C9 C8 C13 119.8(3) . . ? C9 C8 C7 122.1(3) . . ? C13 C8 C7 118.0(3) . . ? C2 C3 H3 120.7 . . ? C2 C3 C4 118.7(3) . . ? C4 C3 H3 120.7 . . ? C3 C4 C7 116.9(3) . . ? C3 C4 C5 117.5(3) . . ? C5 C4 C7 125.6(3) . . ? C8 C13 H13 120.3 . . ? C12 C13 C8 119.4(3) . . ? C12 C13 H13 120.3 . . ? C9 C10 H10 120.0 . . ? C9 C10 C11 120.0(3) . . ? C11 C10 H10 120.0 . . ? N1 C1 C2 121.7(3) . . ? N1 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? O1 C7 C8 122.6(3) . . ? O1 C7 C4 117.4(3) . . ? C8 C7 C4 120.0(3) . . ? F2 C6 C5 111.9(3) . . ? F1 C6 F2 106.5(3) . . ? F1 C6 F3 106.8(3) . . ? F1 C6 C5 112.7(3) . . ? F3 C6 F2 106.3(3) . . ? F3 C6 C5 112.2(3) . . ? N1 C5 C4 123.6(3) . . ? N1 C5 C6 112.5(3) . . ? C4 C5 C6 123.9(3) . . ? C13 C12 H12 119.8 . . ? C13 C12 C11 120.4(3) . . ? C11 C12 H12 119.8 . . ? C10 C11 C12 120.1(3) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? 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 Br1 C2 1.891(3) . ? F2 C6 1.350(4) . ? F1 C6 1.330(4) . ? F3 C6 1.339(4) . ? O1 C7 1.220(4) . ? N1 C1 1.332(5) . ? N1 C5 1.340(4) . ? C2 C3 1.378(5) . ? C2 C1 1.387(5) . ? C9 H9 0.9500 . ? C9 C8 1.391(5) . ? C9 C10 1.383(5) . ? C8 C13 1.414(4) . ? C8 C7 1.473(5) . ? C3 H3 0.9500 . ? C3 C4 1.388(5) . ? C4 C7 1.524(4) . ? C4 C5 1.396(5) . ? C13 H13 0.9500 . ? C13 C12 1.381(5) . ? C10 H10 0.9500 . ? C10 C11 1.392(5) . ? C1 H1 0.9500 . ? C6 C5 1.505(5) . ? C12 H12 0.9500 . ? C12 C11 1.393(5) . ? C11 H11 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 Br1 C2 C3 C4 -178.2(3) . . . . ? Br1 C2 C1 N1 -179.1(3) . . . . ? F2 C6 C5 N1 -158.0(3) . . . . ? F2 C6 C5 C4 22.6(5) . . . . ? F1 C6 C5 N1 -37.9(4) . . . . ? F1 C6 C5 C4 142.6(3) . . . . ? F3 C6 C5 N1 82.6(4) . . . . ? F3 C6 C5 C4 -96.8(4) . . . . ? C2 C3 C4 C7 179.7(3) . . . . ? C2 C3 C4 C5 -3.4(5) . . . . ? C9 C8 C13 C12 -0.7(5) . . . . ? C9 C8 C7 O1 -163.5(4) . . . . ? C9 C8 C7 C4 13.1(5) . . . . ? C9 C10 C11 C12 -0.3(5) . . . . ? C8 C9 C10 C11 0.2(5) . . . . ? C8 C13 C12 C11 0.5(5) . . . . ? C3 C2 C1 N1 0.5(5) . . . . ? C3 C4 C7 O1 62.8(4) . . . . ? C3 C4 C7 C8 -113.9(4) . . . . ? C3 C4 C5 N1 1.9(5) . . . . ? C3 C4 C5 C6 -178.7(3) . . . . ? C13 C8 C7 O1 13.4(5) . . . . ? C13 C8 C7 C4 -170.0(3) . . . . ? C13 C12 C11 C10 0.0(5) . . . . ? C10 C9 C8 C13 0.3(5) . . . . ? C10 C9 C8 C7 177.2(3) . . . . ? C1 N1 C5 C4 0.8(5) . . . . ? C1 N1 C5 C6 -178.6(3) . . . . ? C1 C2 C3 C4 2.3(5) . . . . ? C7 C8 C13 C12 -177.7(3) . . . . ? C7 C4 C5 N1 178.5(3) . . . . ? C7 C4 C5 C6 -2.1(5) . . . . ? C5 N1 C1 C2 -2.0(5) . . . . ? C5 C4 C7 O1 -113.8(4) . . . . ? C5 C4 C7 C8 69.4(5) . . . . ? 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 -5.9952 -0.0631 -0.5857 -0.1836 0.9812 0.0593 5.9952 0.0631 0.5857 0.1836 -0.9812 -0.0593 0.9209 4.7317 -3.1040 -0.0033 -0.0137 -0.9999 2.0944 0.2395 -10.7808 -0.9266 -0.1755 -0.3326 -2.0944 -0.2395 10.7808 0.9266 0.1755 0.3326 -1.1370 -4.4821 4.5385 0.1434 0.0322 0.9891 3.0000 0.0000 7.0000 0.7023 -0.5912 0.1412