#------------------------------------------------------------------------------ #$Date: 2026-06-17 23:23:47 +0100 (Wed, 17 Jun 2026) $ #$Revision: 306587 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/74/1577405.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_1577405 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 'C20 H14 F3 N O2' _chemical_formula_sum 'C20 H14 F3 N O2' _chemical_formula_weight 357.32 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2025-07-22 _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 90.923(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.3940(2) _cell_length_b 21.4396(5) _cell_length_c 9.3120(2) _cell_measurement_reflns_used 4035 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 75.5970 _cell_measurement_theta_min 5.1820 _cell_volume 1675.61(7) _computing_cell_refinement 'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)' _computing_data_collection 'CrysAlisPro system (CCD 44.112a 64-bit (release 21-05-2025))' _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_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.976 _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 -4.00 44.00 0.50 0.76 -- 43.06 20.00-180.00 96 2 \w 64.00 129.00 0.50 0.76 -- 43.06 20.00-180.00 130 3 \w 60.00 135.00 0.50 0.76 -- 45.54 50.00 150.00 150 4 \w -44.00 43.00 0.50 0.76 -- 45.54 50.00 150.00 174 5 \w 156.00 198.00 0.50 4.00 -- 108.20 60.00 30.00 84 6 \w 19.00 77.00 0.50 4.00 -- 108.20 60.00-150.00 116 7 \w 19.00 54.00 0.50 4.00 -- 108.20 60.00 150.00 70 8 \w 36.00 63.00 0.50 4.00 -- 108.20 60.00 30.00 54 9 \w 165.00 197.00 0.50 4.00 -- 108.20 60.00-150.00 64 10 \w 104.00 153.00 0.50 4.00 -- 108.20 60.00 30.00 98 11 \w 80.00 137.00 0.50 4.00 -- 108.20 60.00-150.00 114 12 \w 59.00 197.00 0.50 4.00 -- 108.20 60.00 150.00 276 13 \w 88.00 113.00 0.50 4.00 -- 108.20 0.00 90.00 50 14 \w 37.00 136.00 0.50 4.00 -- 108.20 20.00-150.00 198 15 \w 172.00 198.00 0.50 4.00 -- 108.20 20.00-150.00 52 16 \w 118.00 198.00 0.50 4.00 -- 108.20 40.00 -30.00 160 17 \w 88.00 138.00 0.50 4.00 -- 108.20 50.00 120.00 100 18 \w 151.00 197.00 0.50 4.00 -- 108.20 60.00-180.00 92 19 \w 23.00 52.00 0.50 4.00 -- 108.20 0.00 90.00 58 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC11 (RINC): quarter-chi single' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0084764000 _diffrn_orient_matrix_UB_12 0.0310180000 _diffrn_orient_matrix_UB_13 -0.1491400000 _diffrn_orient_matrix_UB_21 0.0161364000 _diffrn_orient_matrix_UB_22 0.0646416000 _diffrn_orient_matrix_UB_23 0.0708796000 _diffrn_orient_matrix_UB_31 0.1827284000 _diffrn_orient_matrix_UB_32 -0.0042848000 _diffrn_orient_matrix_UB_33 -0.0104367000 _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 0.0370 _diffrn_reflns_av_unetI/netI 0.0415 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.976 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 11328 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.976 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.359 _diffrn_reflns_theta_min 4.124 _diffrn_source 'Rotating-anode X-ray tube (dual wavelength)' _diffrn_source_type 'Rigaku (Cu) X-ray DW Source' _exptl_absorpt_coefficient_mu 0.974 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.968 _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 1.416 _exptl_crystal_description block _exptl_crystal_F_000 736 _exptl_crystal_size_max 0.049 _exptl_crystal_size_mid 0.033 _exptl_crystal_size_min 0.033 _refine_diff_density_max 0.233 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.042 _refine_ls_extinction_coef 0.0020(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/2 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 265 _refine_ls_number_reflns 3432 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.051 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0374 _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^)+(0.0434P)^2^+0.4646P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0956 _refine_ls_wR_factor_ref 0.1015 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2824 _reflns_number_total 3432 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc04438g2.cif _cod_data_source_block s6734l _cod_original_cell_volume 1675.62(7) _cod_database_code 1577405 _shelx_shelxl_version_number 2019/3 _chemical_oxdiff_formula C20H14F3NO2 _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. Others Sof(F3)=Sof(F1)=Sof(F2)=1-FVAR(1) Sof(F6)=Sof(F5)=Sof(F4)=FVAR(1) 3.a Aromatic/amide H refined with riding coordinates: C16(H16), C1(H1), C13(H13), C15(H15), C11(H11), C19(H19), C18(H18), C9(H9), C12(H12), C2(H2), C10(H10) 3.b Idealised Me refined as rotating group: C20(H20A,H20B,H20C) ; _shelx_res_file ; TITL s6734l in P21/n #14 s6734l.res created by SHELXL-2019/3 at 12:25:42 on 22-Jul-2025 CELL 1.54184 8.394041 21.439574 9.312042 90 90.9234 90 ZERR 4 0.00021 0.000462 0.000196 0 0.002 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H F N O UNIT 80 56 12 4 8 L.S. 14 PLAN 5 TEMP -173 CONF BOND fmap 2 MORE -1 BOND $H ACTA REM REM REM WGHT 0.043400 0.464600 EXTI 0.001964 FVAR 3.71877 0.33858 PART 1 F6 3 0.392676 0.675665 0.753606 21.00000 0.10274 0.03489 = 0.03174 -0.00218 -0.00242 -0.02236 PART 0 O1 5 0.206375 0.463461 -0.048652 11.00000 0.04180 0.03126 = 0.03012 -0.00540 -0.00059 -0.00521 O2 5 0.458863 0.568747 0.582918 11.00000 0.02576 0.03306 = 0.03108 0.00636 -0.00036 0.00295 PART 1 F5 3 0.619148 0.719232 0.739054 21.00000 0.02883 0.07437 = 0.04232 0.00063 -0.00583 -0.02378 PART 0 C4 1 0.416938 0.661378 0.451125 11.00000 0.01909 0.02518 = 0.02845 0.00021 0.00168 -0.00015 C16 1 0.376821 0.499241 0.148999 11.00000 0.02768 0.02426 = 0.02503 0.00283 0.00541 0.00044 AFIX 43 H16 2 0.420490 0.458873 0.164481 11.00000 -1.20000 AFIX 0 C5 1 0.468199 0.714746 0.523739 11.00000 0.02400 0.02710 = 0.03324 -0.00185 0.00145 -0.00309 C14 1 0.364733 0.608611 0.211910 11.00000 0.02434 0.02555 = 0.02233 0.00121 0.00453 0.00023 C3 1 0.417198 0.662529 0.300208 11.00000 0.02160 0.02457 = 0.02979 0.00067 0.00275 0.00104 N1 4 0.518184 0.766961 0.460064 11.00000 0.03293 0.02719 = 0.04010 -0.00199 0.00167 -0.00662 C8 1 0.187090 0.594978 0.548142 11.00000 0.02480 0.02340 = 0.02220 -0.00233 0.00132 -0.00149 C1 1 0.515380 0.767769 0.316983 11.00000 0.03604 0.02778 = 0.04028 0.00374 0.00781 -0.00595 AFIX 43 H1 2 0.548521 0.804642 0.269415 11.00000 -1.20000 AFIX 0 C13 1 0.135397 0.547699 0.639623 11.00000 0.02855 0.02691 = 0.02204 0.00049 0.00167 -0.00121 AFIX 43 H13 2 0.211039 0.521734 0.687479 11.00000 -1.20000 AFIX 0 C15 1 0.424359 0.548869 0.235274 11.00000 0.02348 0.02727 = 0.02360 0.00273 0.00407 0.00004 AFIX 43 H15 2 0.498819 0.541924 0.311510 11.00000 -1.20000 AFIX 0 C20 1 0.248242 0.400625 -0.015788 11.00000 0.04818 0.03019 = 0.03850 -0.00523 0.00801 -0.00794 AFIX 137 H20A 2 0.192482 0.372443 -0.082475 11.00000 -1.50000 H20B 2 0.217507 0.390971 0.082831 11.00000 -1.50000 H20C 2 0.363546 0.395225 -0.025109 11.00000 -1.50000 AFIX 0 C7 1 0.360593 0.604190 0.531513 11.00000 0.02522 0.02379 = 0.02041 -0.00249 -0.00022 -0.00071 C17 1 0.264742 0.509076 0.039694 11.00000 0.02839 0.03017 = 0.02251 -0.00218 0.00536 -0.00200 C11 1 -0.136380 0.575930 0.589206 11.00000 0.02406 0.04210 = 0.02996 -0.00106 0.00578 -0.00421 AFIX 43 H11 2 -0.246967 0.569318 0.603143 11.00000 -1.20000 AFIX 0 C19 1 0.254694 0.617883 0.099581 11.00000 0.03020 0.02861 = 0.02412 0.00250 0.00268 0.00501 AFIX 43 H19 2 0.214514 0.658554 0.080886 11.00000 -1.20000 AFIX 0 C18 1 0.204104 0.568567 0.015863 11.00000 0.02973 0.03627 = 0.02352 0.00115 -0.00110 0.00269 AFIX 43 H18 2 0.127316 0.575240 -0.058614 11.00000 -1.20000 AFIX 0 C9 1 0.075288 0.632630 0.477506 11.00000 0.02705 0.02862 = 0.02750 0.00370 0.00220 0.00013 AFIX 43 H9 2 0.109664 0.665007 0.415628 11.00000 -1.20000 AFIX 0 C12 1 -0.025177 0.538679 0.660524 11.00000 0.03112 0.03287 = 0.02617 0.00053 0.00515 -0.00514 AFIX 43 H12 2 -0.059888 0.506904 0.723871 11.00000 -1.20000 AFIX 0 C2 1 0.466559 0.717524 0.234576 11.00000 0.03131 0.02819 = 0.03151 0.00321 0.00724 -0.00089 AFIX 43 H2 2 0.466612 0.720446 0.132780 11.00000 -1.20000 AFIX 0 PART 1 F4 3 0.404845 0.773248 0.729553 21.00000 0.06771 0.05730 = 0.04373 -0.00888 0.00693 0.02775 PART 0 C10 1 -0.086131 0.622771 0.497662 11.00000 0.02489 0.04029 = 0.03127 0.00332 0.00122 0.00418 AFIX 43 H10 2 -0.162335 0.648113 0.448742 11.00000 -1.20000 AFIX 0 C6 1 0.474995 0.719503 0.685665 11.00000 0.03243 0.03013 = 0.03625 -0.00435 -0.00113 -0.00604 PART 2 F3 3 0.383077 0.679223 0.751346 -21.00000 0.04252 0.05598 = 0.02733 -0.00932 0.01093 -0.02139 F1 3 0.437008 0.775226 0.730958 -21.00000 0.12535 0.02980 = 0.03455 -0.01362 -0.00496 -0.00247 F2 3 0.622842 0.708517 0.735158 -21.00000 0.04184 0.13573 = 0.04031 0.00228 -0.01216 0.00911 HKLF 4 REM s6734l in P21/n #14 REM wR2 = 0.1015, GooF = S = 1.051, Restrained GooF = 1.051 for all data REM R1 = 0.0374 for 2824 Fo > 4sig(Fo) and 0.0475 for all 3432 data REM 265 parameters refined using 0 restraints END WGHT 0.0434 0.4646 REM Highest difference peak 0.233, deepest hole -0.182, 1-sigma level 0.042 Q1 1 0.4667 0.7139 0.5971 11.00000 0.05 0.23 Q2 1 0.3547 0.5004 0.0589 11.00000 0.05 0.19 Q3 1 0.4624 0.6845 0.5000 11.00000 0.05 0.17 Q4 1 0.2169 0.5353 0.0331 11.00000 0.05 0.17 Q5 1 0.2597 0.4874 0.2400 11.00000 0.05 0.17 ; _shelx_res_checksum 94150 _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 1.400 _oxdiff_exptl_absorpt_empirical_full_min 0.729 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 F6 F 0.393(2) 0.6757(8) 0.7536(17) 0.056(4) Uani 0.34(6) 1 d . . P A 1 O1 O 0.20638(14) 0.46346(5) -0.04865(12) 0.0344(3) Uani 1 1 d . . . . . O2 O 0.45886(12) 0.56875(5) 0.58292(11) 0.0300(2) Uani 1 1 d . . . . . F5 F 0.6191(18) 0.7192(9) 0.7391(19) 0.049(3) Uani 0.34(6) 1 d . . P A 1 C4 C 0.41694(16) 0.66138(6) 0.45112(15) 0.0242(3) Uani 1 1 d . . . . . C16 C 0.37682(17) 0.49924(6) 0.14900(15) 0.0256(3) Uani 1 1 d . . . . . H16 H 0.420490 0.458873 0.164481 0.031 Uiso 1 1 calc R U . . . C5 C 0.46820(17) 0.71475(7) 0.52374(16) 0.0281(3) Uani 1 1 d . . . . . C14 C 0.36473(16) 0.60861(6) 0.21191(15) 0.0240(3) Uani 1 1 d . . . . . C3 C 0.41720(16) 0.66253(6) 0.30021(16) 0.0253(3) Uani 1 1 d . . . . . N1 N 0.51818(16) 0.76696(6) 0.46006(15) 0.0334(3) Uani 1 1 d . . . . . C8 C 0.18709(16) 0.59498(6) 0.54814(14) 0.0235(3) Uani 1 1 d . . . . . C1 C 0.5154(2) 0.76777(7) 0.31698(18) 0.0346(4) Uani 1 1 d . . . . . H1 H 0.548521 0.804642 0.269415 0.042 Uiso 1 1 calc R U . . . C13 C 0.13540(17) 0.54770(7) 0.63962(14) 0.0258(3) Uani 1 1 d . . . . . H13 H 0.211039 0.521734 0.687479 0.031 Uiso 1 1 calc R U . . . C15 C 0.42436(16) 0.54887(6) 0.23527(15) 0.0247(3) Uani 1 1 d . . . . . H15 H 0.498819 0.541924 0.311510 0.030 Uiso 1 1 calc R U . . . C20 C 0.2482(2) 0.40062(7) -0.01579(19) 0.0389(4) Uani 1 1 d . . . . . H20A H 0.192482 0.372443 -0.082475 0.058 Uiso 1 1 calc R U . . . H20B H 0.217507 0.390971 0.082831 0.058 Uiso 1 1 calc R U . . . H20C H 0.363546 0.395225 -0.025109 0.058 Uiso 1 1 calc R U . . . C7 C 0.36059(16) 0.60419(6) 0.53151(14) 0.0231(3) Uani 1 1 d . . . . . C17 C 0.26474(17) 0.50908(7) 0.03969(15) 0.0270(3) Uani 1 1 d . . . . . C11 C -0.13638(18) 0.57593(8) 0.58921(16) 0.0320(3) Uani 1 1 d . . . . . H11 H -0.246967 0.569318 0.603143 0.038 Uiso 1 1 calc R U . . . C19 C 0.25469(18) 0.61788(7) 0.09958(15) 0.0276(3) Uani 1 1 d . . . . . H19 H 0.214514 0.658554 0.080886 0.033 Uiso 1 1 calc R U . . . C18 C 0.20410(18) 0.56857(7) 0.01586(15) 0.0299(3) Uani 1 1 d . . . . . H18 H 0.127316 0.575240 -0.058614 0.036 Uiso 1 1 calc R U . . . C9 C 0.07529(17) 0.63263(7) 0.47751(15) 0.0277(3) Uani 1 1 d . . . . . H9 H 0.109664 0.665007 0.415628 0.033 Uiso 1 1 calc R U . . . C12 C -0.02518(18) 0.53868(7) 0.66052(16) 0.0300(3) Uani 1 1 d . . . . . H12 H -0.059888 0.506904 0.723871 0.036 Uiso 1 1 calc R U . . . C2 C 0.46656(18) 0.71752(7) 0.23458(17) 0.0303(3) Uani 1 1 d . . . . . H2 H 0.466612 0.720446 0.132780 0.036 Uiso 1 1 calc R U . . . F4 F 0.405(2) 0.7732(8) 0.730(2) 0.056(3) Uani 0.34(6) 1 d . . P A 1 C10 C -0.08613(18) 0.62277(8) 0.49766(16) 0.0321(3) Uani 1 1 d . . . . . H10 H -0.162335 0.648113 0.448742 0.039 Uiso 1 1 calc R U . . . C6 C 0.47500(19) 0.71950(7) 0.68567(18) 0.0330(3) Uani 1 1 d . . . . . F3 F 0.3831(8) 0.6792(4) 0.7513(8) 0.0418(17) Uani 0.66(6) 1 d . . P A 2 F1 F 0.437(2) 0.7752(3) 0.7310(10) 0.0633(19) Uani 0.66(6) 1 d . . P A 2 F2 F 0.6228(11) 0.7085(9) 0.7352(11) 0.073(2) Uani 0.66(6) 1 d . . P A 2 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 F6 0.103(11) 0.035(5) 0.032(6) -0.002(4) -0.002(5) -0.022(4) O1 0.0418(6) 0.0313(5) 0.0301(5) -0.0054(4) -0.0006(4) -0.0052(4) O2 0.0258(5) 0.0331(5) 0.0311(5) 0.0064(4) -0.0004(4) 0.0029(4) F5 0.029(5) 0.074(6) 0.042(4) 0.001(3) -0.006(3) -0.024(4) C4 0.0191(6) 0.0252(7) 0.0284(7) 0.0002(5) 0.0017(5) -0.0002(5) C16 0.0277(7) 0.0243(6) 0.0250(7) 0.0028(5) 0.0054(5) 0.0004(5) C5 0.0240(7) 0.0271(7) 0.0332(8) -0.0019(6) 0.0015(6) -0.0031(5) C14 0.0243(7) 0.0255(7) 0.0223(6) 0.0012(5) 0.0045(5) 0.0002(5) C3 0.0216(7) 0.0246(7) 0.0298(7) 0.0007(5) 0.0028(5) 0.0010(5) N1 0.0329(7) 0.0272(6) 0.0401(7) -0.0020(5) 0.0017(5) -0.0066(5) C8 0.0248(7) 0.0234(6) 0.0222(6) -0.0023(5) 0.0013(5) -0.0015(5) C1 0.0360(8) 0.0278(7) 0.0403(9) 0.0037(6) 0.0078(7) -0.0060(6) C13 0.0286(7) 0.0269(7) 0.0220(6) 0.0005(5) 0.0017(5) -0.0012(5) C15 0.0235(7) 0.0273(7) 0.0236(6) 0.0027(5) 0.0041(5) 0.0000(5) C20 0.0482(10) 0.0302(8) 0.0385(9) -0.0052(7) 0.0080(7) -0.0079(7) C7 0.0252(7) 0.0238(6) 0.0204(6) -0.0025(5) -0.0002(5) -0.0007(5) C17 0.0284(7) 0.0302(7) 0.0225(6) -0.0022(5) 0.0054(5) -0.0020(5) C11 0.0241(7) 0.0421(8) 0.0300(7) -0.0011(6) 0.0058(5) -0.0042(6) C19 0.0302(7) 0.0286(7) 0.0241(7) 0.0025(5) 0.0027(5) 0.0050(5) C18 0.0297(7) 0.0363(8) 0.0235(7) 0.0011(6) -0.0011(5) 0.0027(6) C9 0.0270(7) 0.0286(7) 0.0275(7) 0.0037(6) 0.0022(5) 0.0001(5) C12 0.0311(8) 0.0329(7) 0.0262(7) 0.0005(6) 0.0051(5) -0.0051(6) C2 0.0313(8) 0.0282(7) 0.0315(8) 0.0032(6) 0.0072(6) -0.0009(6) F4 0.068(6) 0.057(7) 0.044(4) -0.009(4) 0.007(3) 0.028(5) C10 0.0249(7) 0.0403(8) 0.0313(8) 0.0033(6) 0.0012(6) 0.0042(6) C6 0.0324(8) 0.0301(8) 0.0363(8) -0.0043(6) -0.0011(6) -0.0060(6) F3 0.043(3) 0.056(4) 0.027(3) -0.009(2) 0.0109(15) -0.0214(17) F1 0.125(5) 0.030(2) 0.035(2) -0.0136(14) -0.005(3) -0.002(3) F2 0.042(3) 0.136(6) 0.040(2) 0.002(3) -0.0122(18) 0.009(3) 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 0 9 5 0.0254 0 -9 -5 0.0109 -5 1 0 0.0145 -5 1 0 0.0145 5 -1 0 0.0182 0 7 -5 0.0254 0 -7 5 0.0073 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 C17 O1 C20 117.62(13) . . ? C5 C4 C3 117.73(13) . . ? C5 C4 C7 121.38(13) . . ? C3 C4 C7 120.89(12) . . ? C15 C16 H16 120.3 . . ? C15 C16 C17 119.48(13) . . ? C17 C16 H16 120.3 . . ? C4 C5 C6 123.08(13) . . ? N1 C5 C4 124.66(14) . . ? N1 C5 C6 112.25(13) . . ? C15 C14 C3 121.92(13) . . ? C15 C14 C19 118.66(13) . . ? C19 C14 C3 119.41(13) . . ? C4 C3 C14 122.41(12) . . ? C2 C3 C4 117.29(13) . . ? C2 C3 C14 120.29(13) . . ? C1 N1 C5 116.98(13) . . ? C13 C8 C7 118.43(12) . . ? C9 C8 C13 119.61(13) . . ? C9 C8 C7 121.95(12) . . ? N1 C1 H1 118.5 . . ? N1 C1 C2 123.08(14) . . ? C2 C1 H1 118.5 . . ? C8 C13 H13 119.9 . . ? C12 C13 C8 120.11(13) . . ? C12 C13 H13 119.9 . . ? C16 C15 C14 121.06(13) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? O1 C20 H20A 109.5 . . ? O1 C20 H20B 109.5 . . ? O1 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O2 C7 C4 119.04(12) . . ? O2 C7 C8 122.58(13) . . ? C8 C7 C4 118.35(12) . . ? O1 C17 C16 124.39(13) . . ? O1 C17 C18 115.76(13) . . ? C18 C17 C16 119.84(13) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C10 C11 C12 120.08(14) . . ? C14 C19 H19 119.7 . . ? C18 C19 C14 120.56(13) . . ? C18 C19 H19 119.7 . . ? C17 C18 H18 119.8 . . ? C19 C18 C17 120.37(14) . . ? C19 C18 H18 119.8 . . ? C8 C9 H9 120.0 . . ? C10 C9 C8 119.96(13) . . ? C10 C9 H9 120.0 . . ? C13 C12 C11 120.18(14) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C3 C2 H2 119.9 . . ? C1 C2 C3 120.25(14) . . ? C1 C2 H2 119.9 . . ? C11 C10 H10 120.0 . . ? C9 C10 C11 120.05(14) . . ? C9 C10 H10 120.0 . . ? F6 C6 C5 114.5(7) . . ? F6 C6 F4 103.0(11) . . ? F5 C6 F6 107.6(10) . . ? F5 C6 C5 113.6(8) . . ? F5 C6 F4 107.1(11) . . ? F4 C6 C5 110.3(9) . . ? F3 C6 C5 114.0(3) . . ? F3 C6 F2 105.8(6) . . ? F1 C6 C5 112.2(5) . . ? F1 C6 F3 107.6(7) . . ? F1 C6 F2 106.2(6) . . ? F2 C6 C5 110.6(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 F6 C6 1.332(14) . ? O1 C20 1.424(2) . ? O1 C17 1.3639(18) . ? O2 C7 1.2142(17) . ? F5 C6 1.301(16) . ? C4 C5 1.394(2) . ? C4 C3 1.406(2) . ? C4 C7 1.5162(19) . ? C16 H16 0.9500 . ? C16 C15 1.388(2) . ? C16 C17 1.391(2) . ? C5 N1 1.337(2) . ? C5 C6 1.511(2) . ? C14 C3 1.481(2) . ? C14 C15 1.3910(19) . ? C14 C19 1.398(2) . ? C3 C2 1.394(2) . ? N1 C1 1.332(2) . ? C8 C13 1.3976(19) . ? C8 C7 1.4803(19) . ? C8 C9 1.395(2) . ? C1 H1 0.9500 . ? C1 C2 1.381(2) . ? C13 H13 0.9500 . ? C13 C12 1.379(2) . ? C15 H15 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C17 C18 1.390(2) . ? C11 H11 0.9500 . ? C11 C12 1.389(2) . ? C11 C10 1.387(2) . ? C19 H19 0.9500 . ? C19 C18 1.377(2) . ? C18 H18 0.9500 . ? C9 H9 0.9500 . ? C9 C10 1.387(2) . ? C12 H12 0.9500 . ? C2 H2 0.9500 . ? F4 C6 1.360(14) . ? C10 H10 0.9500 . ? C6 F3 1.315(6) . ? C6 F1 1.308(8) . ? C6 F2 1.338(11) . ? 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 C17 C18 C19 179.73(13) . . . . ? C4 C5 N1 C1 1.3(2) . . . . ? C4 C5 C6 F6 -15.8(9) . . . . ? C4 C5 C6 F5 108.3(9) . . . . ? C4 C5 C6 F4 -131.4(10) . . . . ? C4 C5 C6 F3 -21.1(5) . . . . ? C4 C5 C6 F1 -143.7(10) . . . . ? C4 C5 C6 F2 97.9(8) . . . . ? C4 C3 C2 C1 1.1(2) . . . . ? C16 C17 C18 C19 0.2(2) . . . . ? C5 C4 C3 C14 -179.79(13) . . . . ? C5 C4 C3 C2 -1.0(2) . . . . ? C5 C4 C7 O2 -79.76(18) . . . . ? C5 C4 C7 C8 98.28(16) . . . . ? C5 N1 C1 C2 -1.1(2) . . . . ? C14 C3 C2 C1 179.97(14) . . . . ? C14 C19 C18 C17 -1.6(2) . . . . ? C3 C4 C5 N1 -0.2(2) . . . . ? C3 C4 C5 C6 -179.51(13) . . . . ? C3 C4 C7 O2 101.06(16) . . . . ? C3 C4 C7 C8 -80.90(16) . . . . ? C3 C14 C15 C16 -178.31(13) . . . . ? C3 C14 C19 C18 179.95(13) . . . . ? N1 C5 C6 F6 164.8(9) . . . . ? N1 C5 C6 F5 -71.1(9) . . . . ? N1 C5 C6 F4 49.2(10) . . . . ? N1 C5 C6 F3 159.5(4) . . . . ? N1 C5 C6 F1 37.0(10) . . . . ? N1 C5 C6 F2 -81.4(8) . . . . ? N1 C1 C2 C3 -0.1(3) . . . . ? C8 C13 C12 C11 0.9(2) . . . . ? C8 C9 C10 C11 0.7(2) . . . . ? C13 C8 C7 O2 7.3(2) . . . . ? C13 C8 C7 C4 -170.70(12) . . . . ? C13 C8 C9 C10 -0.4(2) . . . . ? C15 C16 C17 O1 -178.10(13) . . . . ? C15 C16 C17 C18 1.4(2) . . . . ? C15 C14 C3 C4 -51.14(19) . . . . ? C15 C14 C3 C2 130.08(15) . . . . ? C15 C14 C19 C18 1.3(2) . . . . ? C20 O1 C17 C16 7.9(2) . . . . ? C20 O1 C17 C18 -171.56(13) . . . . ? C7 C4 C5 N1 -179.44(13) . . . . ? C7 C4 C5 C6 1.3(2) . . . . ? C7 C4 C3 C14 -0.6(2) . . . . ? C7 C4 C3 C2 178.23(13) . . . . ? C7 C8 C13 C12 178.44(13) . . . . ? C7 C8 C9 C10 -179.21(13) . . . . ? C17 C16 C15 C14 -1.6(2) . . . . ? C19 C14 C3 C4 130.28(15) . . . . ? C19 C14 C3 C2 -48.49(19) . . . . ? C19 C14 C15 C16 0.3(2) . . . . ? C9 C8 C13 C12 -0.4(2) . . . . ? C9 C8 C7 O2 -173.89(14) . . . . ? C9 C8 C7 C4 8.15(19) . . . . ? C12 C11 C10 C9 -0.2(2) . . . . ? C10 C11 C12 C13 -0.6(2) . . . . ? C6 C5 N1 C1 -179.36(14) . . . . ? 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 0.4767 9.1326 4.5223 -0.3952 0.9186 0.0008 -0.4767 -9.1326 -4.5223 0.3952 -0.9186 -0.0008 -5.4254 0.8292 0.4861 -0.0008 0.0005 -1.0000 -5.4257 0.8283 0.4807 -0.0000 0.0001 -1.0000 5.4257 -0.8283 -0.4807 0.0000 -0.0001 1.0000 -0.1287 7.1403 -5.1843 0.9958 0.0920 0.0000 0.1287 -7.1403 5.1843 -0.9958 -0.0920 -0.0000