#------------------------------------------------------------------------------ #$Date: 2026-06-17 23:23:47 +0100 (Wed, 17 Jun 2026) $ #$Revision: 306587 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/74/1577404.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_1577404 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 'C19 H10 F3 N O2' _chemical_formula_sum 'C19 H10 F3 N O2' _chemical_formula_weight 341.28 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2025-08-05 _audit_creation_method ; Olex2 1.5 (compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308) ; _audit_update_record ; 2025-08-05 deposited with the CCDC. 2026-06-08 downloaded from the CCDC. ; _cell_angle_alpha 104.381(3) _cell_angle_beta 101.852(4) _cell_angle_gamma 95.556(4) _cell_formula_units_Z 2 _cell_length_a 6.3172(3) _cell_length_b 9.4347(4) _cell_length_c 13.0054(5) _cell_measurement_reflns_used 3641 _cell_measurement_temperature 99.98(10) _cell_measurement_theta_max 77.1840 _cell_measurement_theta_min 3.6200 _cell_volume 725.85(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 99.98(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.982 _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 3.00 63.00 0.50 0.10 -- 46.62-104.00 140.00 120 2 \w 37.00 73.00 0.50 0.30 -- 107.75-125.00 120.00 72 3 \w 84.00 112.00 0.50 0.30 -- 107.75-125.00 120.00 56 4 \w 82.00 107.00 0.50 0.30 -- 107.75-104.00 140.00 50 5 \w 36.00 109.00 0.50 0.30 -- 107.75-125.00 0.00 146 6 \w 70.00 104.00 0.50 0.30 -- 107.75 -95.00 -30.00 68 7 \w 40.00 66.00 0.50 0.30 -- 107.75 -95.00-120.00 52 8 \w 68.00 105.00 0.50 0.30 -- 107.75 -95.00-120.00 74 9 \w 36.00 105.00 0.50 0.30 -- 107.75 -95.00-180.00 138 10 \w 42.00 68.00 0.50 0.30 -- 107.75 -61.00 -90.00 52 11 \w -26.00 35.00 0.50 0.10 -- 46.62 -38.00 0.00 122 12 \w -16.00 23.00 0.50 0.10 -- 46.62 -19.00 60.00 78 13 \w 36.00 68.00 0.50 0.30 -- 107.75 -61.00 150.00 64 14 \w 100.00 125.00 0.50 0.30 -- 107.75 104.00-118.00 50 15 \w 100.00 167.00 0.50 0.30 -- 107.75 45.00-150.00 134 16 \w 98.00 175.00 0.50 0.30 -- 107.75 15.00-180.00 154 17 \w 128.00 155.00 0.50 0.30 -- 107.75 104.00-118.00 54 18 \w -106.00 -80.00 0.50 0.30 -- -109.00 104.00-118.00 52 19 \w -79.00 -39.00 0.50 0.30 -- -109.00 125.00-120.00 80 20 \w -90.00 -64.00 0.50 0.10 -- -46.62 125.00 -60.00 52 21 \w -50.00 -23.00 0.50 0.10 -- -46.62 125.00 -90.00 54 22 \w -79.00 -5.00 0.50 0.10 -- -46.62 104.00-118.00 148 23 \w -93.00 -64.00 0.50 0.30 -- -109.00 125.00 0.00 58 24 \w -65.00 -40.00 0.50 0.30 -- -109.00 61.00 0.00 50 25 \w -63.00 -38.00 0.50 0.30 -- -109.00 61.00 30.00 50 26 \w -70.00 -38.00 0.50 0.30 -- -109.00 61.00 60.00 64 27 \w -71.00 -42.00 0.50 0.30 -- -109.00 61.00 90.00 58 28 \w -107.00 -55.00 0.50 0.30 -- -109.00 77.00 150.00 104 29 \w -71.00 -40.00 0.50 0.30 -- -109.00 61.00 -90.00 62 30 \w -136.00 -95.00 0.50 0.30 -- -109.00 -15.00-150.00 82 31 \w -146.00-121.00 0.50 0.30 -- -109.00 -30.00-180.00 50 32 \w -169.00-144.00 0.50 0.30 -- -109.00 -15.00-150.00 50 33 \w -174.00 -96.00 0.50 0.30 -- -109.00 -30.00 -30.00 156 34 \w -86.00 -40.00 0.50 0.10 -- -46.62 -38.00 30.00 92 35 \w -116.00 -24.00 0.50 0.10 -- -46.62 -77.00 150.00 184 36 \w -145.00 -92.00 0.50 0.30 -- -109.00-104.00 140.00 106 37 \w -173.00-109.00 0.50 0.30 -- -109.00 -95.00 0.00 128 ; _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 -0.0000415000 _diffrn_orient_matrix_UB_12 0.0019154000 _diffrn_orient_matrix_UB_13 0.1187889000 _diffrn_orient_matrix_UB_21 0.2474484000 _diffrn_orient_matrix_UB_22 -0.0066735000 _diffrn_orient_matrix_UB_23 0.0237650000 _diffrn_orient_matrix_UB_31 0.0490557000 _diffrn_orient_matrix_UB_32 0.1705155000 _diffrn_orient_matrix_UB_33 0.0342978000 _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 0.0378 _diffrn_reflns_av_unetI/netI 0.0492 _diffrn_reflns_Laue_measured_fraction_full 0.982 _diffrn_reflns_Laue_measured_fraction_max 0.943 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 7026 _diffrn_reflns_point_group_measured_fraction_full 0.982 _diffrn_reflns_point_group_measured_fraction_max 0.943 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 77.783 _diffrn_reflns_theta_min 3.612 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.099 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.878 _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 1.561 _exptl_crystal_description plate _exptl_crystal_F_000 348 _exptl_crystal_size_max 0.138 _exptl_crystal_size_mid 0.066 _exptl_crystal_size_min 0.037 _refine_diff_density_max 0.242 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.051 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 226 _refine_ls_number_reflns 2906 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0405 _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^)+(0.0502P)^2^+0.2211P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1043 _refine_ls_wR_factor_ref 0.1091 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2422 _reflns_number_total 2906 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc04438g2.cif _cod_data_source_block s6739r _cod_original_cell_volume 725.85(5) _cod_database_code 1577404 _shelx_shelxl_version_number 2019/3 _chemical_oxdiff_formula C19H10F3NO2 _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), C2(H2), C16(H16), C17(H17), C1(H1), C18(H18), C12(H12), C13(H13), C15(H15) ; _shelx_res_file ; TITL s6739r_a.res in P-1 s6739r.res created by SHELXL-2019/3 at 14:11:15 on 05-Aug-2025 REM Old TITL s6739r in P-1 REM SHELXT solution in P-1: R1 0.115, Rweak 0.006, Alpha 0.042 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C15 O2 O1 CELL 1.54184 6.317247 9.434694 13.0054 104.3812 101.8518 95.5563 ZERR 2 0.000297 0.00036 0.000494 0.0033 0.0037 0.0035 LATT 1 SFAC C H F N O UNIT 38 20 6 2 4 L.S. 14 PLAN 5 TEMP -173 CONF BOND fmap 2 MORE -1 BOND $H ACTA REM REM REM WGHT 0.050200 0.221100 FVAR 7.67136 F1 3 0.143509 0.509103 0.912939 11.00000 0.04569 0.02191 = 0.03169 0.00271 0.01346 -0.00631 F3 3 0.093461 0.716686 1.012756 11.00000 0.03515 0.03180 = 0.03932 0.00977 0.01903 0.00997 F2 3 0.353802 0.605883 1.072824 11.00000 0.04150 0.04416 = 0.02935 0.02046 0.00698 0.00731 O2 5 -0.160524 0.184426 0.426166 11.00000 0.02082 0.01968 = 0.02017 0.00058 0.00016 0.00143 O1 5 -0.011156 0.655698 0.744645 11.00000 0.02396 0.02846 = 0.02992 -0.00063 0.00496 0.00368 N1 4 0.563956 0.813798 1.010963 11.00000 0.02571 0.02179 = 0.02193 0.00318 0.00037 0.00349 C5 1 0.399792 0.721427 0.935641 11.00000 0.02340 0.01732 = 0.02078 0.00360 0.00343 0.00449 C10 1 0.011463 0.275019 0.506682 11.00000 0.02045 0.01954 = 0.01770 0.00563 0.00062 -0.00018 C4 1 0.367744 0.702834 0.823229 11.00000 0.02343 0.01648 = 0.01989 0.00255 0.00243 0.00492 C11 1 0.210642 0.222699 0.502862 11.00000 0.02335 0.01910 = 0.01782 0.00760 0.00346 0.00342 C19 1 0.157964 0.088079 0.413907 11.00000 0.02447 0.01711 = 0.01692 0.00542 0.00222 0.00000 C14 1 -0.066975 0.070980 0.370702 11.00000 0.02542 0.01911 = 0.01804 0.00564 0.00399 0.00409 C7 1 0.164115 0.613420 0.741503 11.00000 0.02243 0.02021 = 0.02108 0.00539 0.00486 0.00240 C9 1 -0.007885 0.402008 0.581853 11.00000 0.01965 0.02035 = 0.02097 0.00580 0.00363 0.00205 AFIX 43 H9 2 -0.144748 0.435707 0.582098 11.00000 -1.20000 AFIX 0 C3 1 0.525953 0.781013 0.788974 11.00000 0.02472 0.02181 = 0.02177 0.00747 0.00310 0.00430 AFIX 43 H3 2 0.515657 0.768690 0.713269 11.00000 -1.20000 AFIX 0 C8 1 0.184893 0.478735 0.657856 11.00000 0.02381 0.01949 = 0.01799 0.00491 0.00257 0.00019 C6 1 0.247300 0.637546 0.983336 11.00000 0.02967 0.02204 = 0.02148 0.00417 0.00599 0.00436 C2 1 0.697995 0.876645 0.866067 11.00000 0.02266 0.02171 = 0.02996 0.00858 0.00257 0.00127 AFIX 43 H2 2 0.807188 0.931058 0.844358 11.00000 -1.20000 AFIX 0 C16 1 -0.059097 -0.149757 0.239392 11.00000 0.03133 0.01835 = 0.01694 0.00513 0.00287 0.00075 AFIX 43 H16 2 -0.130630 -0.232107 0.179412 11.00000 -1.20000 AFIX 0 C17 1 0.166729 -0.136843 0.281881 11.00000 0.03057 0.02047 = 0.01934 0.00516 0.00449 0.00803 AFIX 43 H17 2 0.244859 -0.210655 0.250587 11.00000 -1.20000 AFIX 0 C1 1 0.707460 0.891279 0.975684 11.00000 0.02390 0.02085 = 0.02642 0.00219 -0.00225 0.00006 AFIX 43 H1 2 0.822305 0.960179 1.028458 11.00000 -1.20000 AFIX 0 C18 1 0.277862 -0.017861 0.368964 11.00000 0.02642 0.02164 = 0.01970 0.00660 0.00372 0.00527 AFIX 43 H18 2 0.431184 -0.008672 0.397247 11.00000 -1.20000 AFIX 0 C12 1 0.401443 0.301256 0.578004 11.00000 0.01994 0.02064 = 0.02360 0.00554 0.00224 0.00299 AFIX 43 H12 2 0.538519 0.268555 0.576074 11.00000 -1.20000 AFIX 0 C13 1 0.386833 0.428460 0.655817 11.00000 0.02159 0.02060 = 0.01983 0.00454 0.00051 0.00075 AFIX 43 H13 2 0.515105 0.482277 0.708418 11.00000 -1.20000 AFIX 0 C15 1 -0.181011 -0.045542 0.282547 11.00000 0.02467 0.02147 = 0.02026 0.00559 0.00087 0.00015 AFIX 43 H15 2 -0.333804 -0.053543 0.253387 11.00000 -1.20000 AFIX 0 HKLF 4 REM s6739r_a.res in P-1 REM wR2 = 0.1091, GooF = S = 1.048, Restrained GooF = 1.048 for all data REM R1 = 0.0405 for 2422 Fo > 4sig(Fo) and 0.0494 for all 2906 data REM 226 parameters refined using 0 restraints END WGHT 0.0502 0.2211 REM Highest difference peak 0.242, deepest hole -0.288, 1-sigma level 0.051 Q1 1 0.3681 0.7268 0.8784 11.00000 0.05 0.24 Q2 1 0.2783 0.6589 0.7829 11.00000 0.05 0.24 Q3 1 0.2186 0.1591 0.4503 11.00000 0.05 0.23 Q4 1 0.0701 -0.1189 0.2452 11.00000 0.05 0.22 Q5 1 0.1891 0.5456 0.6970 11.00000 0.05 0.21 ; _shelx_res_checksum 56720 _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 1.407 _oxdiff_exptl_absorpt_empirical_full_min 0.770 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 F1 F 0.14351(19) 0.50910(11) 0.91294(9) 0.0341(3) Uani 1 1 d . . . . . F3 F 0.09346(18) 0.71669(11) 1.01276(9) 0.0336(3) Uani 1 1 d . . . . . F2 F 0.35380(19) 0.60588(12) 1.07282(9) 0.0366(3) Uani 1 1 d . . . . . O2 O -0.16052(18) 0.18443(12) 0.42617(9) 0.0220(3) Uani 1 1 d . . . . . O1 O -0.0112(2) 0.65570(13) 0.74464(10) 0.0293(3) Uani 1 1 d . . . . . N1 N 0.5640(2) 0.81380(15) 1.01096(11) 0.0245(3) Uani 1 1 d . . . . . C5 C 0.3998(3) 0.72143(16) 0.93564(13) 0.0210(3) Uani 1 1 d . . . . . C10 C 0.0115(3) 0.27502(17) 0.50668(12) 0.0200(3) Uani 1 1 d . . . . . C4 C 0.3677(3) 0.70283(16) 0.82323(12) 0.0207(3) Uani 1 1 d . . . . . C11 C 0.2106(3) 0.22270(16) 0.50286(12) 0.0198(3) Uani 1 1 d . . . . . C19 C 0.1580(3) 0.08808(16) 0.41391(12) 0.0200(3) Uani 1 1 d . . . . . C14 C -0.0670(3) 0.07098(17) 0.37070(12) 0.0209(3) Uani 1 1 d . . . . . C7 C 0.1641(3) 0.61342(17) 0.74150(13) 0.0214(3) Uani 1 1 d . . . . . C9 C -0.0079(3) 0.40201(17) 0.58185(12) 0.0206(3) Uani 1 1 d . . . . . H9 H -0.144748 0.435707 0.582098 0.025 Uiso 1 1 calc R U . . . C3 C 0.5260(3) 0.78101(17) 0.78897(13) 0.0228(3) Uani 1 1 d . . . . . H3 H 0.515657 0.768690 0.713269 0.027 Uiso 1 1 calc R U . . . C8 C 0.1849(3) 0.47873(17) 0.65786(13) 0.0211(3) Uani 1 1 d . . . . . C6 C 0.2473(3) 0.63755(18) 0.98334(13) 0.0247(3) Uani 1 1 d . . . . . C2 C 0.6980(3) 0.87664(17) 0.86607(14) 0.0252(3) Uani 1 1 d . . . . . H2 H 0.807188 0.931058 0.844358 0.030 Uiso 1 1 calc R U . . . C16 C -0.0591(3) -0.14976(17) 0.23939(13) 0.0228(3) Uani 1 1 d . . . . . H16 H -0.130630 -0.232107 0.179412 0.027 Uiso 1 1 calc R U . . . C17 C 0.1667(3) -0.13684(17) 0.28188(13) 0.0235(3) Uani 1 1 d . . . . . H17 H 0.244859 -0.210655 0.250587 0.028 Uiso 1 1 calc R U . . . C1 C 0.7075(3) 0.89128(18) 0.97568(14) 0.0260(4) Uani 1 1 d . . . . . H1 H 0.822305 0.960179 1.028458 0.031 Uiso 1 1 calc R U . . . C18 C 0.2779(3) -0.01786(17) 0.36896(13) 0.0226(3) Uani 1 1 d . . . . . H18 H 0.431184 -0.008672 0.397247 0.027 Uiso 1 1 calc R U . . . C12 C 0.4014(3) 0.30126(17) 0.57800(13) 0.0219(3) Uani 1 1 d . . . . . H12 H 0.538519 0.268555 0.576074 0.026 Uiso 1 1 calc R U . . . C13 C 0.3868(3) 0.42846(17) 0.65582(13) 0.0217(3) Uani 1 1 d . . . . . H13 H 0.515105 0.482277 0.708418 0.026 Uiso 1 1 calc R U . . . C15 C -0.1810(3) -0.04554(17) 0.28255(13) 0.0231(3) Uani 1 1 d . . . . . H15 H -0.333804 -0.053543 0.253387 0.028 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 F1 0.0457(7) 0.0219(5) 0.0317(6) 0.0027(4) 0.0135(5) -0.0063(4) F3 0.0352(6) 0.0318(5) 0.0393(6) 0.0098(4) 0.0190(5) 0.0100(4) F2 0.0415(6) 0.0442(6) 0.0293(5) 0.0205(5) 0.0070(5) 0.0073(5) O2 0.0208(6) 0.0197(5) 0.0202(5) 0.0006(4) 0.0002(4) 0.0014(4) O1 0.0240(6) 0.0285(6) 0.0299(6) -0.0006(5) 0.0050(5) 0.0037(5) N1 0.0257(7) 0.0218(7) 0.0219(7) 0.0032(5) 0.0004(6) 0.0035(5) C5 0.0234(8) 0.0173(7) 0.0208(8) 0.0036(6) 0.0034(6) 0.0045(6) C10 0.0205(8) 0.0195(7) 0.0177(7) 0.0056(6) 0.0006(6) -0.0002(6) C4 0.0234(8) 0.0165(7) 0.0199(7) 0.0026(6) 0.0024(6) 0.0049(6) C11 0.0234(8) 0.0191(7) 0.0178(7) 0.0076(6) 0.0035(6) 0.0034(6) C19 0.0245(8) 0.0171(7) 0.0169(7) 0.0054(6) 0.0022(6) 0.0000(6) C14 0.0254(8) 0.0191(7) 0.0180(7) 0.0056(6) 0.0040(6) 0.0041(6) C7 0.0224(8) 0.0202(7) 0.0211(7) 0.0054(6) 0.0049(6) 0.0024(6) C9 0.0196(8) 0.0203(7) 0.0210(7) 0.0058(6) 0.0036(6) 0.0021(6) C3 0.0247(8) 0.0218(7) 0.0218(8) 0.0075(6) 0.0031(6) 0.0043(6) C8 0.0238(8) 0.0195(7) 0.0180(7) 0.0049(6) 0.0026(6) 0.0002(6) C6 0.0297(9) 0.0220(8) 0.0215(8) 0.0042(6) 0.0060(7) 0.0044(6) C2 0.0227(8) 0.0217(8) 0.0300(9) 0.0086(6) 0.0026(7) 0.0013(6) C16 0.0313(9) 0.0184(7) 0.0169(7) 0.0051(6) 0.0029(6) 0.0008(6) C17 0.0306(9) 0.0205(7) 0.0193(7) 0.0052(6) 0.0045(6) 0.0080(6) C1 0.0239(8) 0.0208(8) 0.0264(8) 0.0022(6) -0.0023(6) 0.0001(6) C18 0.0264(8) 0.0216(7) 0.0197(8) 0.0066(6) 0.0037(6) 0.0053(6) C12 0.0199(8) 0.0206(7) 0.0236(8) 0.0055(6) 0.0022(6) 0.0030(6) C13 0.0216(8) 0.0206(7) 0.0198(7) 0.0045(6) 0.0005(6) 0.0008(6) C15 0.0247(8) 0.0215(8) 0.0203(8) 0.0056(6) 0.0009(6) 0.0001(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' 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 -4 1 4 0.0097 4 -1 -4 0.0254 -1 6 -4 0.0410 1 -6 3 0.0521 -2 1 -6 0.0385 2 -2 6 0.0184 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 C10 O2 C14 105.04(12) . . ? C1 N1 C5 117.29(14) . . ? N1 C5 C4 124.25(15) . . ? N1 C5 C6 113.42(14) . . ? C4 C5 C6 122.33(15) . . ? O2 C10 C11 111.81(13) . . ? C9 C10 O2 124.75(14) . . ? C9 C10 C11 123.44(15) . . ? C5 C4 C7 122.73(14) . . ? C3 C4 C5 116.87(14) . . ? C3 C4 C7 120.20(14) . . ? C10 C11 C19 105.53(13) . . ? C12 C11 C10 119.40(14) . . ? C12 C11 C19 135.07(15) . . ? C14 C19 C11 105.78(14) . . ? C14 C19 C18 119.47(14) . . ? C18 C19 C11 134.75(15) . . ? O2 C14 C19 111.84(13) . . ? C15 C14 O2 124.71(15) . . ? C15 C14 C19 123.45(15) . . ? O1 C7 C4 118.84(14) . . ? O1 C7 C8 122.16(15) . . ? C8 C7 C4 118.98(14) . . ? C10 C9 H9 121.7 . . ? C10 C9 C8 116.51(15) . . ? C8 C9 H9 121.7 . . ? C4 C3 H3 120.3 . . ? C2 C3 C4 119.50(15) . . ? C2 C3 H3 120.3 . . ? C9 C8 C7 116.81(15) . . ? C9 C8 C13 121.15(15) . . ? C13 C8 C7 122.03(14) . . ? F1 C6 F3 107.23(14) . . ? F1 C6 F2 106.90(13) . . ? F1 C6 C5 112.39(13) . . ? F3 C6 C5 111.35(13) . . ? F2 C6 F3 106.74(13) . . ? F2 C6 C5 111.91(14) . . ? C3 C2 H2 120.8 . . ? C3 C2 C1 118.50(15) . . ? C1 C2 H2 120.8 . . ? C17 C16 H16 119.1 . . ? C15 C16 H16 119.1 . . ? C15 C16 C17 121.79(15) . . ? C16 C17 H17 119.5 . . ? C18 C17 C16 120.98(15) . . ? C18 C17 H17 119.5 . . ? N1 C1 C2 123.46(15) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C19 C18 H18 120.9 . . ? C17 C18 C19 118.14(15) . . ? C17 C18 H18 120.9 . . ? C11 C12 H12 120.7 . . ? C13 C12 C11 118.53(15) . . ? C13 C12 H12 120.7 . . ? C8 C13 H13 119.5 . . ? C12 C13 C8 120.95(15) . . ? C12 C13 H13 119.5 . . ? C14 C15 C16 116.15(15) . . ? C14 C15 H15 121.9 . . ? C16 C15 H15 121.9 . . ? 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 F1 C6 1.336(2) . ? F3 C6 1.342(2) . ? F2 C6 1.337(2) . ? O2 C10 1.3841(19) . ? O2 C14 1.3890(19) . ? O1 C7 1.218(2) . ? N1 C5 1.333(2) . ? N1 C1 1.333(2) . ? C5 C4 1.398(2) . ? C5 C6 1.510(2) . ? C10 C11 1.401(2) . ? C10 C9 1.379(2) . ? C4 C7 1.510(2) . ? C4 C3 1.395(2) . ? C11 C19 1.447(2) . ? C11 C12 1.393(2) . ? C19 C14 1.394(2) . ? C19 C18 1.397(2) . ? C14 C15 1.387(2) . ? C7 C8 1.490(2) . ? C9 H9 0.9500 . ? C9 C8 1.401(2) . ? C3 H3 0.9500 . ? C3 C2 1.383(2) . ? C8 C13 1.406(2) . ? C2 H2 0.9500 . ? C2 C1 1.386(2) . ? C16 H16 0.9500 . ? C16 C17 1.402(2) . ? C16 C15 1.387(2) . ? C17 H17 0.9500 . ? C17 C18 1.387(2) . ? C1 H1 0.9500 . ? C18 H18 0.9500 . ? C12 H12 0.9500 . ? C12 C13 1.389(2) . ? C13 H13 0.9500 . ? C15 H15 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 O2 C10 C11 C19 -0.75(17) . . . . ? O2 C10 C11 C12 179.67(13) . . . . ? O2 C10 C9 C8 179.50(14) . . . . ? O2 C14 C15 C16 -178.76(14) . . . . ? O1 C7 C8 C9 0.2(2) . . . . ? O1 C7 C8 C13 -178.67(15) . . . . ? N1 C5 C4 C7 -171.41(14) . . . . ? N1 C5 C4 C3 3.6(2) . . . . ? N1 C5 C6 F1 -154.67(14) . . . . ? N1 C5 C6 F3 85.01(17) . . . . ? N1 C5 C6 F2 -34.36(19) . . . . ? C5 N1 C1 C2 -2.2(2) . . . . ? C5 C4 C7 O1 64.3(2) . . . . ? C5 C4 C7 C8 -117.35(17) . . . . ? C5 C4 C3 C2 -3.0(2) . . . . ? C10 O2 C14 C19 -0.12(16) . . . . ? C10 O2 C14 C15 -179.82(15) . . . . ? C10 C11 C19 C14 0.63(16) . . . . ? C10 C11 C19 C18 -178.43(16) . . . . ? C10 C11 C12 C13 1.0(2) . . . . ? C10 C9 C8 C7 -178.14(13) . . . . ? C10 C9 C8 C13 0.7(2) . . . . ? C4 C5 C6 F1 25.7(2) . . . . ? C4 C5 C6 F3 -94.61(17) . . . . ? C4 C5 C6 F2 146.02(15) . . . . ? C4 C7 C8 C9 -178.17(14) . . . . ? C4 C7 C8 C13 3.0(2) . . . . ? C4 C3 C2 C1 0.2(2) . . . . ? C11 C10 C9 C8 -0.8(2) . . . . ? C11 C19 C14 O2 -0.33(17) . . . . ? C11 C19 C14 C15 179.37(14) . . . . ? C11 C19 C18 C17 179.19(16) . . . . ? C11 C12 C13 C8 -1.1(2) . . . . ? C19 C11 C12 C13 -178.40(16) . . . . ? C19 C14 C15 C16 1.6(2) . . . . ? C14 O2 C10 C11 0.55(16) . . . . ? C14 O2 C10 C9 -179.70(14) . . . . ? C14 C19 C18 C17 0.2(2) . . . . ? C7 C4 C3 C2 172.11(14) . . . . ? C7 C8 C13 C12 179.00(14) . . . . ? C9 C10 C11 C19 179.49(14) . . . . ? C9 C10 C11 C12 -0.1(2) . . . . ? C9 C8 C13 C12 0.2(2) . . . . ? C3 C4 C7 O1 -110.54(18) . . . . ? C3 C4 C7 C8 67.84(19) . . . . ? C3 C2 C1 N1 2.6(3) . . . . ? C6 C5 C4 C7 8.2(2) . . . . ? C6 C5 C4 C3 -176.86(14) . . . . ? C16 C17 C18 C19 0.6(2) . . . . ? C17 C16 C15 C14 -0.7(2) . . . . ? C1 N1 C5 C4 -1.0(2) . . . . ? C1 N1 C5 C6 179.41(14) . . . . ? C18 C19 C14 O2 178.91(13) . . . . ? C18 C19 C14 C15 -1.4(2) . . . . ? C12 C11 C19 C14 -179.89(17) . . . . ? C12 C11 C19 C18 1.0(3) . . . . ? C15 C16 C17 C18 -0.4(2) . . . . ? 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 -3.8900 0.9002 3.9924 0.4761 -0.8737 0.0996 3.9011 -0.7739 -4.0030 -0.4772 0.8754 -0.0779 -1.1595 5.6502 -4.2027 -0.4884 -0.4245 0.7624 0.6397 -6.0946 2.5883 0.2958 0.2605 -0.9191 -1.9696 1.4018 -6.3968 -0.7571 -0.6487 -0.0770 1.9693 -1.5236 6.4069 0.7581 0.6497 0.0565