#------------------------------------------------------------------------------ #$Date: 2026-06-17 23:23:47 +0100 (Wed, 17 Jun 2026) $ #$Revision: 306587 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/74/1577411.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_1577411 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 H11 F3 N2 O2' _chemical_formula_sum 'C19 H11 F3 N2 O2' _chemical_formula_weight 356.30 _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 2025-11-10 _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 108.6911(14) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.7181(2) _cell_length_b 7.14966(9) _cell_length_c 15.2683(2) _cell_measurement_reflns_used 7699 _cell_measurement_temperature 99.98(10) _cell_measurement_theta_max 77.1020 _cell_measurement_theta_min 3.0370 _cell_volume 1521.94(4) _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 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 0.998 _diffrn_measured_fraction_theta_max 0.964 _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 -24.00 20.00 0.50 0.05 -- 46.64 -19.00 0.00 88 2 \w 26.00 51.00 0.50 0.05 -- 46.64-115.00 -87.00 50 3 \w 48.00 73.00 0.50 0.05 -- 107.75-115.00 -87.00 50 4 \w 35.00 104.00 0.50 0.05 -- 107.75 -95.00 -90.00 138 5 \w 36.00 62.00 0.50 0.05 -- 107.75 -61.00 -60.00 52 6 \w 95.00 172.00 0.50 0.05 -- 107.75 45.00 0.00 154 7 \w 104.00 129.00 0.50 0.05 -- 107.75 115.00 1.00 50 8 \w 71.00 97.00 0.50 0.05 -- 107.75 174.00 141.00 52 9 \w 72.00 114.00 0.50 0.05 -- 46.64 174.00 141.00 84 10 \w -5.00 21.00 0.50 0.05 -- -46.64 19.00 -90.00 52 11 \w -20.00 28.00 0.50 0.05 -- -46.64 19.00 -30.00 96 12 \w -22.00 29.00 0.50 0.05 -- -46.64 19.00 -60.00 102 13 \w -13.00 29.00 0.50 0.05 -- -46.64 19.00-180.00 84 14 \w -104.00 -75.00 0.50 0.05 -- -109.00 125.00 -60.00 58 15 \w -108.00 -44.00 0.50 0.05 -- -109.00 115.00 1.00 128 16 \w -63.00 -37.00 0.50 0.05 -- -109.00 61.00 90.00 52 17 \w -71.00 -40.00 0.50 0.05 -- -109.00 61.00 30.00 62 18 \w -71.00 -41.00 0.50 0.05 -- -109.00 61.00 0.00 60 19 \w -69.00 -37.00 0.50 0.05 -- -109.00 61.00 -30.00 64 20 \w -65.00 -40.00 0.50 0.05 -- -109.00 61.00 -60.00 50 21 \w -82.00 -52.00 0.50 0.05 -- -46.64 115.00 1.00 60 22 \w -65.00 -36.00 0.50 0.05 -- -109.00 61.00-180.00 58 23 \w -150.00-124.00 0.50 0.05 -- -109.00 -30.00 -60.00 52 24 \w -174.00 -98.00 0.50 0.05 -- -109.00 -45.00-180.00 152 25 \w -117.00 -61.00 0.50 0.05 -- -46.64-174.00 131.00 112 26 \w -101.00 -69.00 0.50 0.05 -- -109.00-174.00 131.00 64 ; _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 0.0750984000 _diffrn_orient_matrix_UB_12 -0.1547529000 _diffrn_orient_matrix_UB_13 0.0079622000 _diffrn_orient_matrix_UB_21 0.0694640000 _diffrn_orient_matrix_UB_22 0.1455631000 _diffrn_orient_matrix_UB_23 -0.0174289000 _diffrn_orient_matrix_UB_31 0.0417547000 _diffrn_orient_matrix_UB_32 0.0358530000 _diffrn_orient_matrix_UB_33 0.1047625000 _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 0.0196 _diffrn_reflns_av_unetI/netI 0.0190 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.964 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 9873 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.964 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 77.602 _diffrn_reflns_theta_min 3.170 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.094 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_correction_T_min 0.924 _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 1.555 _exptl_crystal_description block _exptl_crystal_F_000 728 _exptl_crystal_size_max 0.175 _exptl_crystal_size_mid 0.151 _exptl_crystal_size_min 0.112 _refine_diff_density_max 0.274 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.044 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 236 _refine_ls_number_reflns 3120 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.0359 _refine_ls_R_factor_gt 0.0330 _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^)+(0.0404P)^2^+0.7208P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0836 _refine_ls_wR_factor_ref 0.0856 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2863 _reflns_number_total 3120 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc04438g2.cif _cod_data_source_block s6783r _cod_database_code 1577411 _shelx_shelxl_version_number 2019/3 _chemical_oxdiff_formula C19H11F3N2O2 _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: C15(H15), C10(H10), C3(H3), C12(H12), C11(H11), C16(H16), C4(H4), C17(H17) 2.b Idealised Me refined as rotating group: C1(H1A,H1B,H1C) ; _shelx_res_file ; TITL s6783r_a.res in P2(1)/c s6783r.res created by SHELXL-2019/3 at 17:58:43 on 10-Nov-2025 REM Old TITL s6783r in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.117, Rweak 0.149, Alpha 0.036 REM 0.586 for 216 systematic absences, Orientation as input REM Formula found by SHELXT: C1 N2 O2 CELL 1.54184 14.718086 7.149665 15.268334 90 108.6911 90 ZERR 4 0.000198 0.000093 0.000207 0 0.0014 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F N O UNIT 76 44 12 8 8 L.S. 14 PLAN 5 TEMP -173 CONF BOND fmap 2 MORE -1 BOND $H ACTA REM REM REM WGHT 0.040400 0.720800 FVAR 6.66091 F1 3 0.799694 0.132668 0.574851 11.00000 0.04988 0.02812 = 0.01827 -0.00515 0.00853 -0.01201 F2 3 0.854097 -0.071486 0.680941 11.00000 0.03876 0.01803 = 0.04249 -0.00562 -0.00522 0.00590 F3 3 0.715218 0.046528 0.658242 11.00000 0.02329 0.04819 = 0.04205 -0.01662 0.01282 -0.01525 O1 5 0.697505 0.557266 0.635757 11.00000 0.01542 0.01979 = 0.01554 0.00201 0.00602 0.00207 O2 5 0.960654 0.405465 0.594679 11.00000 0.02018 0.03124 = 0.02348 0.00253 0.01073 0.00462 N1 4 0.559994 0.599693 0.678475 11.00000 0.01719 0.01809 = 0.01873 -0.00212 0.00594 -0.00035 N2 4 0.850022 0.192900 0.815681 11.00000 0.02423 0.02424 = 0.01883 0.00318 0.00670 -0.00130 C14 1 0.883764 0.405773 0.707519 11.00000 0.01271 0.01693 = 0.01689 0.00067 0.00389 0.00271 C15 1 0.922971 0.532565 0.779121 11.00000 0.01722 0.01803 = 0.02061 -0.00011 0.00439 0.00129 AFIX 43 H15 2 0.947429 0.649234 0.766982 11.00000 -1.20000 AFIX 0 C5 1 0.572128 0.712204 0.531500 11.00000 0.01857 0.01399 = 0.01724 -0.00171 0.00328 -0.00134 C6 1 0.605026 0.624616 0.617537 11.00000 0.01420 0.01514 = 0.01867 -0.00185 0.00317 -0.00021 C13 1 0.889444 0.453212 0.612932 11.00000 0.01763 0.01566 = 0.01800 -0.00170 0.00668 -0.00230 C8 1 0.723737 0.605045 0.559457 11.00000 0.01908 0.01425 = 0.01339 -0.00148 0.00501 -0.00268 C18 1 0.848480 0.238668 0.730469 11.00000 0.01468 0.01837 = 0.01748 0.00063 0.00444 0.00161 C7 1 0.650130 0.701957 0.493357 11.00000 0.01837 0.01408 = 0.01647 -0.00181 0.00315 -0.00166 C10 1 0.822666 0.622615 0.463729 11.00000 0.02364 0.01840 = 0.01845 -0.00201 0.00903 -0.00206 AFIX 43 H10 2 0.881096 0.596593 0.452177 11.00000 -1.20000 AFIX 0 C9 1 0.811116 0.561448 0.546774 11.00000 0.01869 0.01495 = 0.01651 -0.00108 0.00583 -0.00135 C3 1 0.427769 0.756041 0.566544 11.00000 0.01593 0.01767 = 0.02713 -0.00332 0.00280 0.00111 AFIX 43 H3 2 0.363793 0.801011 0.550693 11.00000 -1.20000 AFIX 0 C2 1 0.469371 0.667777 0.652040 11.00000 0.01784 0.01636 = 0.02442 -0.00538 0.00614 -0.00156 C12 1 0.664126 0.761237 0.411652 11.00000 0.02466 0.01688 = 0.01544 0.00165 0.00250 -0.00047 AFIX 43 H12 2 0.615420 0.828131 0.366403 11.00000 -1.20000 AFIX 0 C19 1 0.804339 0.086812 0.660943 11.00000 0.01803 0.01857 = 0.02113 0.00107 0.00531 -0.00116 C11 1 0.750904 0.720400 0.397750 11.00000 0.02889 0.02075 = 0.01529 0.00124 0.00812 -0.00295 AFIX 43 H11 2 0.761350 0.759886 0.342338 11.00000 -1.20000 AFIX 0 C16 1 0.925870 0.486701 0.867916 11.00000 0.02322 0.02406 = 0.01674 -0.00338 0.00248 0.00202 AFIX 43 H16 2 0.952810 0.570618 0.917736 11.00000 -1.20000 AFIX 0 C4 1 0.478290 0.778865 0.504744 11.00000 0.01940 0.01616 = 0.02116 -0.00051 0.00080 -0.00012 AFIX 43 H4 2 0.450084 0.837572 0.446510 11.00000 -1.20000 AFIX 0 C17 1 0.888693 0.315786 0.882935 11.00000 0.02955 0.02943 = 0.01503 0.00234 0.00662 0.00059 AFIX 43 H17 2 0.890919 0.284899 0.944104 11.00000 -1.20000 AFIX 0 C1 1 0.415405 0.646590 0.719893 11.00000 0.01993 0.02630 = 0.02911 -0.00568 0.01087 -0.00108 AFIX 137 H1A 2 0.437119 0.533327 0.756828 11.00000 -1.50000 H1B 2 0.346595 0.636777 0.686359 11.00000 -1.50000 H1C 2 0.427278 0.755836 0.760779 11.00000 -1.50000 AFIX 0 HKLF 4 REM s6783r_a.res in P2(1)/c REM wR2 = 0.0856, GooF = S = 1.043, Restrained GooF = 1.043 for all data REM R1 = 0.0330 for 2863 Fo > 4sig(Fo) and 0.0359 for all 3120 data REM 236 parameters refined using 0 restraints END WGHT 0.0404 0.7208 REM Highest difference peak 0.274, deepest hole -0.268, 1-sigma level 0.044 Q1 1 0.7009 0.6860 0.5357 11.00000 0.05 0.27 Q2 1 0.6852 0.6451 0.5172 11.00000 0.05 0.27 Q3 1 0.5849 0.6969 0.5767 11.00000 0.05 0.26 Q4 1 0.8294 0.1754 0.6950 11.00000 0.05 0.26 Q5 1 0.8853 0.4238 0.6587 11.00000 0.05 0.26 ; _shelx_res_checksum 41041 _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 1.115 _oxdiff_exptl_absorpt_empirical_full_min 0.939 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 F1 F 0.79969(7) 0.13267(12) 0.57485(5) 0.0327(2) Uani 1 1 d . . . . . F2 F 0.85410(6) -0.07149(12) 0.68094(6) 0.0374(2) Uani 1 1 d . . . . . F3 F 0.71522(6) 0.04653(14) 0.65824(6) 0.0373(2) Uani 1 1 d . . . . . O1 O 0.69750(6) 0.55727(12) 0.63576(6) 0.01666(18) Uani 1 1 d . . . . . O2 O 0.96065(6) 0.40546(14) 0.59468(6) 0.0241(2) Uani 1 1 d . . . . . N1 N 0.55999(7) 0.59969(14) 0.67848(7) 0.0180(2) Uani 1 1 d . . . . . N2 N 0.85002(8) 0.19290(16) 0.81568(7) 0.0225(2) Uani 1 1 d . . . . . C14 C 0.88376(8) 0.40577(17) 0.70752(8) 0.0157(2) Uani 1 1 d . . . . . C15 C 0.92297(8) 0.53256(18) 0.77912(8) 0.0190(3) Uani 1 1 d . . . . . H15 H 0.947429 0.649234 0.766982 0.023 Uiso 1 1 calc R U . . . C5 C 0.57213(8) 0.71220(17) 0.53150(8) 0.0172(2) Uani 1 1 d . . . . . C6 C 0.60503(8) 0.62462(17) 0.61754(8) 0.0165(2) Uani 1 1 d . . . . . C13 C 0.88944(8) 0.45321(17) 0.61293(8) 0.0169(2) Uani 1 1 d . . . . . C8 C 0.72374(8) 0.60505(16) 0.55946(8) 0.0156(2) Uani 1 1 d . . . . . C18 C 0.84848(8) 0.23867(17) 0.73047(8) 0.0170(2) Uani 1 1 d . . . . . C7 C 0.65013(8) 0.70196(16) 0.49336(8) 0.0169(2) Uani 1 1 d . . . . . C10 C 0.82267(9) 0.62262(18) 0.46373(8) 0.0196(3) Uani 1 1 d . . . . . H10 H 0.881096 0.596593 0.452177 0.024 Uiso 1 1 calc R U . . . C9 C 0.81112(8) 0.56145(17) 0.54677(8) 0.0167(2) Uani 1 1 d . . . . . C3 C 0.42777(9) 0.75604(18) 0.56654(9) 0.0212(3) Uani 1 1 d . . . . . H3 H 0.363793 0.801011 0.550693 0.025 Uiso 1 1 calc R U . . . C2 C 0.46937(9) 0.66778(17) 0.65204(9) 0.0197(3) Uani 1 1 d . . . . . C12 C 0.66413(9) 0.76124(17) 0.41165(8) 0.0199(3) Uani 1 1 d . . . . . H12 H 0.615420 0.828131 0.366403 0.024 Uiso 1 1 calc R U . . . C19 C 0.80434(9) 0.08681(18) 0.66094(8) 0.0195(3) Uani 1 1 d . . . . . C11 C 0.75090(9) 0.72040(18) 0.39775(8) 0.0214(3) Uani 1 1 d . . . . . H11 H 0.761350 0.759886 0.342338 0.026 Uiso 1 1 calc R U . . . C16 C 0.92587(9) 0.48670(19) 0.86792(8) 0.0223(3) Uani 1 1 d . . . . . H16 H 0.952810 0.570618 0.917736 0.027 Uiso 1 1 calc R U . . . C4 C 0.47829(9) 0.77886(17) 0.50474(9) 0.0203(3) Uani 1 1 d . . . . . H4 H 0.450084 0.837572 0.446510 0.024 Uiso 1 1 calc R U . . . C17 C 0.88869(10) 0.3158(2) 0.88293(8) 0.0248(3) Uani 1 1 d . . . . . H17 H 0.890919 0.284899 0.944104 0.030 Uiso 1 1 calc R U . . . C1 C 0.41540(9) 0.6466(2) 0.71989(9) 0.0244(3) Uani 1 1 d . . . . . H1A H 0.437119 0.533327 0.756828 0.037 Uiso 1 1 calc R U . . . H1B H 0.346595 0.636777 0.686359 0.037 Uiso 1 1 calc R U . . . H1C H 0.427278 0.755836 0.760779 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 F1 0.0499(5) 0.0281(4) 0.0183(4) -0.0052(3) 0.0085(3) -0.0120(4) F2 0.0388(5) 0.0180(4) 0.0425(5) -0.0056(3) -0.0052(4) 0.0059(3) F3 0.0233(4) 0.0482(6) 0.0420(5) -0.0166(4) 0.0128(4) -0.0152(4) O1 0.0154(4) 0.0198(4) 0.0155(4) 0.0020(3) 0.0060(3) 0.0021(3) O2 0.0202(4) 0.0312(5) 0.0235(5) 0.0025(4) 0.0107(4) 0.0046(4) N1 0.0172(5) 0.0181(5) 0.0187(5) -0.0021(4) 0.0059(4) -0.0003(4) N2 0.0242(5) 0.0242(6) 0.0188(5) 0.0032(4) 0.0067(4) -0.0013(4) C14 0.0127(5) 0.0169(6) 0.0169(6) 0.0007(4) 0.0039(4) 0.0027(4) C15 0.0172(5) 0.0180(6) 0.0206(6) -0.0001(5) 0.0044(4) 0.0013(5) C5 0.0186(6) 0.0140(5) 0.0172(6) -0.0017(4) 0.0033(4) -0.0013(4) C6 0.0142(5) 0.0151(5) 0.0187(6) -0.0019(4) 0.0032(4) -0.0002(4) C13 0.0176(5) 0.0157(6) 0.0180(6) -0.0017(4) 0.0067(4) -0.0023(4) C8 0.0191(6) 0.0143(5) 0.0134(5) -0.0015(4) 0.0050(4) -0.0027(4) C18 0.0147(5) 0.0184(6) 0.0175(6) 0.0006(5) 0.0044(4) 0.0016(4) C7 0.0184(5) 0.0141(5) 0.0165(5) -0.0018(4) 0.0032(4) -0.0017(4) C10 0.0236(6) 0.0184(6) 0.0184(6) -0.0020(5) 0.0090(5) -0.0021(5) C9 0.0187(6) 0.0149(5) 0.0165(6) -0.0011(4) 0.0058(4) -0.0014(4) C3 0.0159(5) 0.0177(6) 0.0271(6) -0.0033(5) 0.0028(5) 0.0011(5) C2 0.0178(6) 0.0164(6) 0.0244(6) -0.0054(5) 0.0061(5) -0.0016(5) C12 0.0247(6) 0.0169(6) 0.0154(5) 0.0016(4) 0.0025(5) -0.0005(5) C19 0.0180(6) 0.0186(6) 0.0211(6) 0.0011(5) 0.0053(5) -0.0012(5) C11 0.0289(6) 0.0207(6) 0.0153(6) 0.0012(5) 0.0081(5) -0.0029(5) C16 0.0232(6) 0.0241(6) 0.0167(6) -0.0034(5) 0.0025(5) 0.0020(5) C4 0.0194(6) 0.0162(6) 0.0212(6) -0.0005(5) 0.0008(5) -0.0001(5) C17 0.0295(7) 0.0294(7) 0.0150(6) 0.0023(5) 0.0066(5) 0.0006(6) C1 0.0199(6) 0.0263(7) 0.0291(7) -0.0057(5) 0.0109(5) -0.0011(5) 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 1 0 0 0.0588 -1 0 0 0.0532 -1 0 2 0.0582 -2 -1 1 0.0630 2 1 -1 0.0551 0 0 -1 0.0792 0 1 2 0.0801 0 1 0 0.0672 0 1 -2 0.0839 -1 -1 1 0.0694 -2 -2 -1 0.0725 2 -1 0 0.0582 2 2 -1 0.0475 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 C8 O1 C6 105.46(9) . . ? C6 N1 C2 114.31(10) . . ? C17 N2 C18 117.33(11) . . ? C15 C14 C13 117.86(11) . . ? C18 C14 C15 117.04(11) . . ? C18 C14 C13 124.93(11) . . ? C14 C15 H15 120.3 . . ? C16 C15 C14 119.31(12) . . ? C16 C15 H15 120.3 . . ? C6 C5 C7 106.01(10) . . ? C4 C5 C6 116.25(11) . . ? C4 C5 C7 137.72(11) . . ? O1 C6 C5 111.56(10) . . ? N1 C6 O1 119.73(10) . . ? N1 C6 C5 128.70(11) . . ? O2 C13 C14 118.12(11) . . ? O2 C13 C9 121.93(11) . . ? C9 C13 C14 119.91(10) . . ? O1 C8 C7 111.60(10) . . ? O1 C8 C9 125.47(10) . . ? C9 C8 C7 122.92(11) . . ? N2 C18 C14 124.39(11) . . ? N2 C18 C19 112.19(11) . . ? C14 C18 C19 123.42(11) . . ? C8 C7 C5 105.35(10) . . ? C12 C7 C5 135.16(11) . . ? C12 C7 C8 119.48(11) . . ? C9 C10 H10 119.1 . . ? C11 C10 H10 119.1 . . ? C11 C10 C9 121.83(12) . . ? C8 C9 C13 124.85(11) . . ? C8 C9 C10 116.10(11) . . ? C10 C9 C13 119.04(11) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C4 C3 C2 121.18(11) . . ? N1 C2 C3 122.27(11) . . ? N1 C2 C1 116.51(11) . . ? C3 C2 C1 121.21(11) . . ? C7 C12 H12 120.7 . . ? C11 C12 C7 118.62(11) . . ? C11 C12 H12 120.7 . . ? F1 C19 C18 112.95(10) . . ? F2 C19 F1 106.61(10) . . ? F2 C19 F3 106.73(11) . . ? F2 C19 C18 111.65(10) . . ? F3 C19 F1 106.48(10) . . ? F3 C19 C18 112.01(10) . . ? C10 C11 H11 119.5 . . ? C12 C11 C10 121.05(11) . . ? C12 C11 H11 119.5 . . ? C15 C16 H16 120.6 . . ? C15 C16 C17 118.76(12) . . ? C17 C16 H16 120.6 . . ? C5 C4 H4 121.4 . . ? C3 C4 C5 117.26(11) . . ? C3 C4 H4 121.4 . . ? N2 C17 C16 123.16(12) . . ? N2 C17 H17 118.4 . . ? C16 C17 H17 118.4 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 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 F1 C19 1.3351(15) . ? F2 C19 1.3293(15) . ? F3 C19 1.3306(14) . ? O1 C6 1.3854(14) . ? O1 C8 1.3825(14) . ? O2 C13 1.2165(15) . ? N1 C6 1.3160(16) . ? N1 C2 1.3542(15) . ? N2 C18 1.3347(16) . ? N2 C17 1.3326(17) . ? C14 C15 1.3949(17) . ? C14 C13 1.5117(16) . ? C14 C18 1.3916(17) . ? C15 H15 0.9500 . ? C15 C16 1.3821(17) . ? C5 C6 1.3945(17) . ? C5 C7 1.4461(17) . ? C5 C4 1.3928(17) . ? C13 C9 1.4839(16) . ? C8 C7 1.4041(16) . ? C8 C9 1.3958(16) . ? C18 C19 1.5119(17) . ? C7 C12 1.3939(17) . ? C10 H10 0.9500 . ? C10 C9 1.4021(17) . ? C10 C11 1.3918(18) . ? C3 H3 0.9500 . ? C3 C2 1.4017(18) . ? C3 C4 1.3855(18) . ? C2 C1 1.5015(17) . ? C12 H12 0.9500 . ? C12 C11 1.3912(18) . ? C11 H11 0.9500 . ? C16 H16 0.9500 . ? C16 C17 1.3877(19) . ? C4 H4 0.9500 . ? C17 H17 0.9500 . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 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 O1 C8 C7 C5 -0.83(13) . . . . ? O1 C8 C7 C12 180.00(10) . . . . ? O1 C8 C9 C13 1.17(19) . . . . ? O1 C8 C9 C10 179.61(11) . . . . ? O2 C13 C9 C8 173.50(12) . . . . ? O2 C13 C9 C10 -4.90(18) . . . . ? N2 C18 C19 F1 178.16(10) . . . . ? N2 C18 C19 F2 -61.70(14) . . . . ? N2 C18 C19 F3 57.94(14) . . . . ? C14 C15 C16 C17 -0.58(18) . . . . ? C14 C13 C9 C8 -8.88(18) . . . . ? C14 C13 C9 C10 172.72(11) . . . . ? C14 C18 C19 F1 -2.24(17) . . . . ? C14 C18 C19 F2 117.90(13) . . . . ? C14 C18 C19 F3 -122.46(12) . . . . ? C15 C14 C13 O2 87.89(14) . . . . ? C15 C14 C13 C9 -89.82(13) . . . . ? C15 C14 C18 N2 -0.12(18) . . . . ? C15 C14 C18 C19 -179.67(11) . . . . ? C15 C16 C17 N2 -0.1(2) . . . . ? C5 C7 C12 C11 -178.20(13) . . . . ? C6 O1 C8 C7 0.26(13) . . . . ? C6 O1 C8 C9 -178.59(11) . . . . ? C6 N1 C2 C3 0.36(17) . . . . ? C6 N1 C2 C1 -178.77(11) . . . . ? C6 C5 C7 C8 1.06(13) . . . . ? C6 C5 C7 C12 -179.97(13) . . . . ? C6 C5 C4 C3 1.50(17) . . . . ? C13 C14 C15 C16 -174.86(11) . . . . ? C13 C14 C18 N2 175.05(11) . . . . ? C13 C14 C18 C19 -4.50(18) . . . . ? C8 O1 C6 N1 179.87(11) . . . . ? C8 O1 C6 C5 0.46(13) . . . . ? C8 C7 C12 C11 0.66(18) . . . . ? C18 N2 C17 C16 0.59(19) . . . . ? C18 C14 C15 C16 0.66(17) . . . . ? C18 C14 C13 O2 -87.25(15) . . . . ? C18 C14 C13 C9 95.04(14) . . . . ? C7 C5 C6 O1 -0.97(13) . . . . ? C7 C5 C6 N1 179.69(12) . . . . ? C7 C5 C4 C3 179.49(14) . . . . ? C7 C8 C9 C13 -177.55(11) . . . . ? C7 C8 C9 C10 0.89(17) . . . . ? C7 C12 C11 C10 -0.06(19) . . . . ? C9 C8 C7 C5 178.05(11) . . . . ? C9 C8 C7 C12 -1.12(18) . . . . ? C9 C10 C11 C12 -0.1(2) . . . . ? C2 N1 C6 O1 -178.56(10) . . . . ? C2 N1 C6 C5 0.74(18) . . . . ? C2 C3 C4 C5 -0.60(18) . . . . ? C11 C10 C9 C13 178.28(11) . . . . ? C11 C10 C9 C8 -0.26(18) . . . . ? C4 C5 C6 O1 177.63(10) . . . . ? C4 C5 C6 N1 -1.72(19) . . . . ? C4 C5 C7 C8 -177.07(14) . . . . ? C4 C5 C7 C12 1.9(3) . . . . ? C4 C3 C2 N1 -0.40(19) . . . . ? C4 C3 C2 C1 178.69(12) . . . . ? C17 N2 C18 C14 -0.49(18) . . . . ? C17 N2 C18 C19 179.10(11) . . . . ? 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 1.0009 0.0002 -0.0003 0.0751 0.0696 0.0418 -1.0009 -0.0002 0.0003 -0.0751 -0.0696 -0.0418 -0.9989 0.0004 1.9984 -0.0592 -0.1042 0.1677 -2.0004 -1.0003 0.9997 0.0125 -0.3020 -0.0147 2.0004 1.0003 -0.9997 -0.0125 0.3020 0.0147 -0.0010 -0.0003 -0.9991 -0.0080 0.0173 -0.1047 0.0016 1.0008 1.9981 -0.1388 0.1110 0.2453 -0.0004 1.0003 0.0000 -0.1548 0.1456 0.0358 -0.0025 0.9997 -1.9981 -0.1708 0.1802 -0.1736 -0.9994 -1.0002 0.9994 0.0877 -0.2324 0.0271 -2.0020 -2.0012 -0.9984 0.1514 -0.4130 -0.2599 2.0023 -0.9999 -0.0007 0.3051 -0.0065 0.0477 1.9999 2.0006 -0.9997 -0.1674 0.4476 0.0505