#------------------------------------------------------------------------------ #$Date: 2026-06-17 23:23:47 +0100 (Wed, 17 Jun 2026) $ #$Revision: 306587 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/74/1577406.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_1577406 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 'C25 H14 F3 N O S' _chemical_formula_sum 'C25 H14 F3 N O S' _chemical_formula_weight 433.43 _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 2025-07-23 _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 91.2344(14) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.36426(13) _cell_length_b 25.5739(4) _cell_length_c 9.21252(14) _cell_measurement_reflns_used 7282 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 76.7400 _cell_measurement_theta_min 3.4670 _cell_volume 1970.16(5) _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 100.00(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.957 _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 48.00 74.00 0.50 0.12 -- 107.75 -77.00-150.00 52 2 \w 89.00 114.00 0.50 0.12 -- 107.75 -77.00-150.00 50 3 \w 117.00 143.00 0.50 0.12 -- 107.75 84.00 101.00 52 4 \w 36.00 73.00 0.50 0.12 -- 107.75 -61.00 150.00 74 5 \w 35.00 72.00 0.50 0.12 -- 107.75 -61.00 120.00 74 6 \w 41.00 118.00 0.50 0.05 -- 46.87 38.00-180.00 154 7 \w 35.00 60.00 0.50 0.12 -- 107.75 -61.00-180.00 50 8 \w 35.00 74.00 0.50 0.12 -- 107.75-125.00-150.00 78 9 \w 81.00 110.00 0.50 0.12 -- 107.75-125.00-150.00 58 10 \w 40.00 87.00 0.50 0.12 -- 107.75 -84.00 -18.00 94 11 \w 14.00 45.00 0.50 0.05 -- 46.87 -84.00 -18.00 62 12 \w -22.00 29.00 0.50 0.05 -- -46.87 19.00 -90.00 102 13 \w -112.00 -37.00 0.50 0.12 -- -109.00 77.00 -60.00 150 14 \w -71.00 -38.00 0.50 0.12 -- -109.00 61.00 60.00 66 15 \w -71.00 -46.00 0.50 0.12 -- -109.00 61.00 30.00 50 16 \w -67.00 -39.00 0.50 0.12 -- -109.00 61.00 90.00 56 17 \w -71.00 -43.00 0.50 0.12 -- -109.00 61.00 120.00 56 18 \w -22.00 29.00 0.50 0.05 -- -46.87 19.00 30.00 102 19 \w -64.00 24.00 0.50 0.05 -- -46.87 84.00 101.00 176 20 \w -105.00 -79.00 0.50 0.12 -- -109.00 84.00 101.00 52 21 \w -172.00 -95.00 0.50 0.12 -- -109.00 -15.00-180.00 154 22 \w -164.00 -90.00 0.50 0.12 -- -109.00 -84.00 -18.00 148 ; _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 0.1327833000 _diffrn_orient_matrix_UB_12 0.0396688000 _diffrn_orient_matrix_UB_13 0.0385982000 _diffrn_orient_matrix_UB_21 -0.1232938000 _diffrn_orient_matrix_UB_22 0.0350660000 _diffrn_orient_matrix_UB_23 0.0746996000 _diffrn_orient_matrix_UB_31 0.0326864000 _diffrn_orient_matrix_UB_32 -0.0287226000 _diffrn_orient_matrix_UB_33 0.1447164000 _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 0.0489 _diffrn_reflns_av_unetI/netI 0.0495 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.957 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 12451 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.957 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 77.990 _diffrn_reflns_theta_min 3.456 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.867 _exptl_absorpt_correction_T_max 0.978 _exptl_absorpt_correction_T_min 0.874 _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 1.461 _exptl_crystal_description block _exptl_crystal_F_000 888 _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.075 _exptl_crystal_size_min 0.053 _refine_diff_density_max 0.279 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.050 _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 280 _refine_ls_number_reflns 4032 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0375 _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^)+(0.0373P)^2^+0.5699P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0895 _refine_ls_wR_factor_ref 0.0943 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3333 _reflns_number_total 4032 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc04438g2.cif _cod_data_source_block s6735r _cod_database_code 1577406 _shelx_shelxl_version_number 2019/3 _chemical_oxdiff_formula C25H14F3NOS _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: C8(H8), C25(H25), C21(H21), C2(H2), C14(H14), C24(H24), C5(H5), C11(H11), C3(H3), C22(H22), C10(H10), C4(H4), C15(H15), C23(H23) ; _shelx_res_file ; TITL s6735r_a.res in P2(1)/n s6735r.res created by SHELXL-2019/3 at 12:05:47 on 23-Jul-2025 REM Old TITL s6735r in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.122, Rweak 0.107, Alpha 0.036 REM 0.368 for 59 systematic absences, Orientation as input REM Formula found by SHELXT: C25 N F3 Cl CELL 1.54184 8.364256 25.573864 9.212518 90 91.2344 90 ZERR 4 0.000125 0.000376 0.000138 0 0.0014 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H F N O S UNIT 100 56 12 4 4 4 L.S. 14 PLAN 5 TEMP -173 CONF BOND fmap 2 MORE -1 BOND $H ACTA REM REM REM WGHT 0.037300 0.569900 FVAR 3.91183 S1 6 0.367203 0.509570 1.154170 11.00000 0.02784 0.02426 = 0.02092 -0.00135 -0.00452 -0.00014 F2 3 0.197966 0.310525 0.340173 11.00000 0.03717 0.02817 = 0.02619 -0.00444 0.00242 -0.00434 F1 3 0.168328 0.228204 0.366756 11.00000 0.08163 0.02217 = 0.03437 -0.00767 -0.00337 0.00765 O1 5 0.122513 0.402911 0.507843 11.00000 0.02339 0.02294 = 0.02522 0.00222 -0.00226 0.00371 F3 3 -0.037789 0.278107 0.350521 11.00000 0.03323 0.06233 = 0.04051 0.00437 -0.01407 -0.00967 N1 4 0.059811 0.236705 0.635488 11.00000 0.02762 0.02092 = 0.03661 0.00027 -0.00083 -0.00528 C8 1 0.160224 0.420708 0.854155 11.00000 0.01855 0.02241 = 0.01894 0.00219 0.00142 0.00021 AFIX 43 H8 2 0.089228 0.426743 0.774025 11.00000 -1.20000 AFIX 0 C20 1 0.394478 0.381558 0.552300 11.00000 0.02249 0.02168 = 0.01647 -0.00212 -0.00077 -0.00200 C19 1 0.219442 0.373227 0.562891 11.00000 0.02212 0.01835 = 0.01628 -0.00322 -0.00111 0.00011 C17 1 0.162035 0.325175 0.643475 11.00000 0.01592 0.01964 = 0.02657 0.00094 0.00046 0.00039 C25 1 0.447973 0.425270 0.475980 11.00000 0.02820 0.02564 = 0.02167 0.00096 0.00113 -0.00265 AFIX 43 H25 2 0.372833 0.449564 0.436649 11.00000 -1.20000 AFIX 0 C13 1 0.159404 0.324812 0.796465 11.00000 0.01708 0.02002 = 0.02770 0.00039 0.00150 0.00190 C9 1 0.212485 0.370121 0.885896 11.00000 0.02179 0.02075 = 0.02131 0.00095 0.00319 -0.00009 C18 1 0.110402 0.274515 0.407584 11.00000 0.02933 0.02015 = 0.03187 -0.00247 -0.00651 -0.00150 C21 1 0.506187 0.346570 0.611860 11.00000 0.02217 0.02797 = 0.02222 0.00261 0.00113 0.00294 AFIX 43 H21 2 0.470959 0.317027 0.664888 11.00000 -1.20000 AFIX 0 C2 1 0.247440 0.602333 1.029572 11.00000 0.02784 0.02341 = 0.02489 -0.00409 0.00241 -0.00233 AFIX 43 H2 2 0.302574 0.622482 1.101368 11.00000 -1.20000 AFIX 0 C7 1 0.212328 0.462279 0.940118 11.00000 0.01792 0.02215 = 0.01969 0.00139 0.00311 -0.00002 C16 1 0.111593 0.280203 0.571057 11.00000 0.01986 0.02079 = 0.03217 -0.00171 -0.00187 0.00077 C6 1 0.178451 0.517588 0.923060 11.00000 0.01967 0.02156 = 0.02007 -0.00085 0.00374 -0.00084 C14 1 0.108429 0.278898 0.862980 11.00000 0.02659 0.02451 = 0.02925 0.00307 0.00401 -0.00069 AFIX 43 H14 2 0.106872 0.276741 0.965886 11.00000 -1.20000 AFIX 0 C12 1 0.315027 0.452432 1.060699 11.00000 0.01884 0.02550 = 0.02001 -0.00016 0.00041 0.00023 C24 1 0.609064 0.433207 0.457666 11.00000 0.03155 0.03327 = 0.02635 0.00198 0.00532 -0.00671 AFIX 43 H24 2 0.644493 0.462727 0.404653 11.00000 -1.20000 AFIX 0 C5 1 0.083879 0.542469 0.817008 11.00000 0.02094 0.02386 = 0.01889 0.00049 0.00146 -0.00031 AFIX 43 H5 2 0.027765 0.522495 0.745449 11.00000 -1.20000 AFIX 0 C11 1 0.367050 0.401976 1.093155 11.00000 0.02487 0.02785 = 0.02064 0.00204 -0.00151 0.00213 AFIX 43 H11 2 0.436585 0.395669 1.174162 11.00000 -1.20000 AFIX 0 C1 1 0.257102 0.547994 1.029505 11.00000 0.01955 0.02466 = 0.02041 -0.00009 0.00322 0.00028 C3 1 0.155192 0.626156 0.922025 11.00000 0.02936 0.01844 = 0.02980 0.00036 0.00469 0.00020 AFIX 43 H3 2 0.147896 0.663217 0.919504 11.00000 -1.20000 AFIX 0 C22 1 0.668299 0.354882 0.593725 11.00000 0.02227 0.04165 = 0.02441 0.00060 -0.00081 0.00503 AFIX 43 H22 2 0.743895 0.330963 0.634144 11.00000 -1.20000 AFIX 0 C10 1 0.315854 0.361392 1.005678 11.00000 0.02439 0.02247 = 0.02359 0.00410 0.00270 0.00425 AFIX 43 H10 2 0.351073 0.326842 1.026694 11.00000 -1.20000 AFIX 0 C4 1 0.072590 0.596653 0.817077 11.00000 0.02492 0.02385 = 0.02506 0.00335 0.00402 0.00363 AFIX 43 H4 2 0.008298 0.613767 0.745313 11.00000 -1.20000 AFIX 0 C15 1 0.060337 0.236672 0.779996 11.00000 0.03023 0.02353 = 0.03771 0.00507 0.00218 -0.00583 AFIX 43 H15 2 0.025829 0.206001 0.828344 11.00000 -1.20000 AFIX 0 C23 1 0.720603 0.398140 0.516526 11.00000 0.02012 0.04624 = 0.02601 -0.00370 0.00205 -0.00564 AFIX 43 H23 2 0.831706 0.403783 0.503935 11.00000 -1.20000 AFIX 0 HKLF 4 REM s6735r_a.res in P2(1)/n REM wR2 = 0.0943, GooF = S = 1.048, Restrained GooF = 1.048 for all data REM R1 = 0.0375 for 3333 Fo > 4sig(Fo) and 0.0480 for all 4032 data REM 280 parameters refined using 0 restraints END WGHT 0.0373 0.5628 REM Highest difference peak 0.279, deepest hole -0.302, 1-sigma level 0.050 Q1 1 0.1842 0.3470 0.8430 11.00000 0.05 0.28 Q2 1 0.1839 0.3467 0.6060 11.00000 0.05 0.23 Q3 1 0.0189 0.2130 0.5810 11.00000 0.05 0.21 Q4 1 0.3391 0.4773 1.0994 11.00000 0.05 0.21 Q5 1 0.2926 0.4618 0.9761 11.00000 0.05 0.20 ; _shelx_res_checksum 844 _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 1.187 _oxdiff_exptl_absorpt_empirical_full_min 0.860 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 S1 S 0.36720(5) 0.50957(2) 1.15417(4) 0.02441(12) Uani 1 1 d . . . . . F2 F 0.19797(13) 0.31053(4) 0.34017(11) 0.0305(2) Uani 1 1 d . . . . . F1 F 0.16833(19) 0.22820(4) 0.36676(13) 0.0461(3) Uani 1 1 d . . . . . O1 O 0.12251(14) 0.40291(5) 0.50784(13) 0.0239(3) Uani 1 1 d . . . . . F3 F -0.03779(15) 0.27811(5) 0.35052(14) 0.0456(3) Uani 1 1 d . . . . . N1 N 0.05981(19) 0.23671(6) 0.63549(18) 0.0284(3) Uani 1 1 d . . . . . C8 C 0.16022(19) 0.42071(6) 0.85415(18) 0.0200(3) Uani 1 1 d . . . . . H8 H 0.089228 0.426743 0.774025 0.024 Uiso 1 1 calc R U . . . C20 C 0.3945(2) 0.38156(6) 0.55230(17) 0.0202(3) Uani 1 1 d . . . . . C19 C 0.2194(2) 0.37323(6) 0.56289(17) 0.0189(3) Uani 1 1 d . . . . . C17 C 0.16203(19) 0.32518(6) 0.64347(18) 0.0207(3) Uani 1 1 d . . . . . C25 C 0.4480(2) 0.42527(7) 0.47598(19) 0.0252(4) Uani 1 1 d . . . . . H25 H 0.372833 0.449564 0.436649 0.030 Uiso 1 1 calc R U . . . C13 C 0.15940(19) 0.32481(6) 0.79646(19) 0.0216(3) Uani 1 1 d . . . . . C9 C 0.2125(2) 0.37012(6) 0.88590(18) 0.0212(3) Uani 1 1 d . . . . . C18 C 0.1104(2) 0.27451(7) 0.4076(2) 0.0272(4) Uani 1 1 d . . . . . C21 C 0.5062(2) 0.34657(7) 0.61186(19) 0.0241(4) Uani 1 1 d . . . . . H21 H 0.470959 0.317027 0.664888 0.029 Uiso 1 1 calc R U . . . C2 C 0.2474(2) 0.60233(7) 1.02957(19) 0.0254(4) Uani 1 1 d . . . . . H2 H 0.302574 0.622482 1.101368 0.030 Uiso 1 1 calc R U . . . C7 C 0.21233(19) 0.46228(6) 0.94012(17) 0.0199(3) Uani 1 1 d . . . . . C16 C 0.1116(2) 0.28020(7) 0.5711(2) 0.0243(4) Uani 1 1 d . . . . . C6 C 0.1785(2) 0.51759(6) 0.92306(18) 0.0204(3) Uani 1 1 d . . . . . C14 C 0.1084(2) 0.27890(7) 0.8630(2) 0.0267(4) Uani 1 1 d . . . . . H14 H 0.106872 0.276741 0.965886 0.032 Uiso 1 1 calc R U . . . C12 C 0.3150(2) 0.45243(7) 1.06070(18) 0.0214(3) Uani 1 1 d . . . . . C24 C 0.6091(2) 0.43321(8) 0.4577(2) 0.0303(4) Uani 1 1 d . . . . . H24 H 0.644493 0.462727 0.404653 0.036 Uiso 1 1 calc R U . . . C5 C 0.0839(2) 0.54247(7) 0.81701(18) 0.0212(3) Uani 1 1 d . . . . . H5 H 0.027765 0.522495 0.745449 0.025 Uiso 1 1 calc R U . . . C11 C 0.3671(2) 0.40198(7) 1.09316(19) 0.0245(4) Uani 1 1 d . . . . . H11 H 0.436585 0.395669 1.174162 0.029 Uiso 1 1 calc R U . . . C1 C 0.2571(2) 0.54799(7) 1.02950(18) 0.0215(3) Uani 1 1 d . . . . . C3 C 0.1552(2) 0.62616(7) 0.9220(2) 0.0258(4) Uani 1 1 d . . . . . H3 H 0.147896 0.663217 0.919504 0.031 Uiso 1 1 calc R U . . . C22 C 0.6683(2) 0.35488(8) 0.5937(2) 0.0295(4) Uani 1 1 d . . . . . H22 H 0.743895 0.330963 0.634144 0.035 Uiso 1 1 calc R U . . . C10 C 0.3159(2) 0.36139(7) 1.00568(19) 0.0235(4) Uani 1 1 d . . . . . H10 H 0.351073 0.326842 1.026694 0.028 Uiso 1 1 calc R U . . . C4 C 0.0726(2) 0.59665(7) 0.81708(19) 0.0246(4) Uani 1 1 d . . . . . H4 H 0.008298 0.613767 0.745313 0.029 Uiso 1 1 calc R U . . . C15 C 0.0603(2) 0.23667(7) 0.7800(2) 0.0305(4) Uani 1 1 d . . . . . H15 H 0.025829 0.206001 0.828344 0.037 Uiso 1 1 calc R U . . . C23 C 0.7206(2) 0.39814(8) 0.5165(2) 0.0308(4) Uani 1 1 d . . . . . H23 H 0.831706 0.403783 0.503935 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 S1 0.0278(2) 0.0243(2) 0.0209(2) -0.00135(16) -0.00452(16) -0.00014(16) F2 0.0372(6) 0.0282(5) 0.0262(5) -0.0044(4) 0.0024(4) -0.0043(5) F1 0.0816(10) 0.0222(5) 0.0344(6) -0.0077(5) -0.0034(6) 0.0077(6) O1 0.0234(6) 0.0229(6) 0.0252(6) 0.0022(5) -0.0023(5) 0.0037(5) F3 0.0332(6) 0.0623(8) 0.0405(7) 0.0044(6) -0.0141(5) -0.0097(6) N1 0.0276(8) 0.0209(7) 0.0366(9) 0.0003(6) -0.0008(7) -0.0053(6) C8 0.0186(8) 0.0224(8) 0.0189(8) 0.0022(6) 0.0014(6) 0.0002(6) C20 0.0225(8) 0.0217(8) 0.0165(7) -0.0021(6) -0.0008(6) -0.0020(6) C19 0.0221(8) 0.0184(7) 0.0163(7) -0.0032(6) -0.0011(6) 0.0001(6) C17 0.0159(7) 0.0196(8) 0.0266(8) 0.0009(6) 0.0005(6) 0.0004(6) C25 0.0282(9) 0.0256(9) 0.0217(8) 0.0010(7) 0.0011(7) -0.0026(7) C13 0.0171(7) 0.0200(8) 0.0277(9) 0.0004(7) 0.0015(6) 0.0019(6) C9 0.0218(8) 0.0208(8) 0.0213(8) 0.0009(6) 0.0032(6) -0.0001(6) C18 0.0293(9) 0.0202(8) 0.0319(9) -0.0025(7) -0.0065(7) -0.0015(7) C21 0.0222(8) 0.0280(9) 0.0222(8) 0.0026(7) 0.0011(7) 0.0029(7) C2 0.0278(9) 0.0234(8) 0.0249(9) -0.0041(7) 0.0024(7) -0.0023(7) C7 0.0179(8) 0.0222(8) 0.0197(8) 0.0014(6) 0.0031(6) 0.0000(6) C16 0.0199(8) 0.0208(8) 0.0322(9) -0.0017(7) -0.0019(7) 0.0008(7) C6 0.0197(8) 0.0216(8) 0.0201(8) -0.0008(6) 0.0037(6) -0.0008(6) C14 0.0266(9) 0.0245(9) 0.0292(9) 0.0031(7) 0.0040(7) -0.0007(7) C12 0.0188(8) 0.0255(8) 0.0200(8) -0.0002(6) 0.0004(6) 0.0002(6) C24 0.0316(10) 0.0333(10) 0.0263(9) 0.0020(7) 0.0053(7) -0.0067(8) C5 0.0209(8) 0.0239(8) 0.0189(8) 0.0005(6) 0.0015(6) -0.0003(6) C11 0.0249(8) 0.0279(9) 0.0206(8) 0.0020(7) -0.0015(7) 0.0021(7) C1 0.0196(8) 0.0247(8) 0.0204(8) -0.0001(6) 0.0032(6) 0.0003(6) C3 0.0294(9) 0.0184(8) 0.0298(9) 0.0004(7) 0.0047(7) 0.0002(7) C22 0.0223(9) 0.0416(11) 0.0244(9) 0.0006(8) -0.0008(7) 0.0050(8) C10 0.0244(8) 0.0225(8) 0.0236(8) 0.0041(7) 0.0027(7) 0.0042(7) C4 0.0249(8) 0.0239(8) 0.0251(9) 0.0033(7) 0.0040(7) 0.0036(7) C15 0.0302(9) 0.0235(9) 0.0377(10) 0.0051(8) 0.0022(8) -0.0058(7) C23 0.0201(9) 0.0462(11) 0.0260(9) -0.0037(8) 0.0020(7) -0.0056(8) 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' S S 0.3331 0.5567 '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 -16 1 0.0461 1 16 0 0.0301 2 1 6 0.0327 -2 -2 -6 0.0187 1 -16 0 0.0385 0 -8 -5 0.0342 -1 16 0 0.0359 -4 -1 4 0.0489 -5 6 -1 0.0528 5 -4 -1 0.0377 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 C12 S1 C1 91.36(8) . . ? C15 N1 C16 116.76(16) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C7 C8 C9 119.80(15) . . ? C25 C20 C19 118.30(15) . . ? C21 C20 C19 122.29(15) . . ? C21 C20 C25 119.38(16) . . ? O1 C19 C20 122.25(15) . . ? O1 C19 C17 119.66(15) . . ? C20 C19 C17 118.08(14) . . ? C13 C17 C19 120.38(14) . . ? C16 C17 C19 122.04(15) . . ? C16 C17 C13 117.58(16) . . ? C20 C25 H25 119.9 . . ? C24 C25 C20 120.25(17) . . ? C24 C25 H25 119.9 . . ? C17 C13 C9 122.60(15) . . ? C14 C13 C17 117.13(16) . . ? C14 C13 C9 120.25(16) . . ? C8 C9 C13 121.28(15) . . ? C8 C9 C10 119.79(16) . . ? C10 C9 C13 118.92(15) . . ? F2 C18 F3 106.37(14) . . ? F2 C18 C16 113.83(14) . . ? F1 C18 F2 105.90(16) . . ? F1 C18 F3 106.76(15) . . ? F1 C18 C16 111.76(15) . . ? F3 C18 C16 111.74(16) . . ? C20 C21 H21 119.9 . . ? C22 C21 C20 120.13(17) . . ? C22 C21 H21 119.9 . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? C3 C2 C1 118.08(16) . . ? C8 C7 C6 128.75(15) . . ? C8 C7 C12 119.32(15) . . ? C12 C7 C6 111.91(15) . . ? N1 C16 C17 124.95(17) . . ? N1 C16 C18 111.51(15) . . ? C17 C16 C18 123.54(16) . . ? C5 C6 C7 128.78(15) . . ? C5 C6 C1 119.07(15) . . ? C1 C6 C7 112.14(15) . . ? C13 C14 H14 119.9 . . ? C15 C14 C13 120.27(17) . . ? C15 C14 H14 119.9 . . ? C7 C12 S1 112.33(12) . . ? C11 C12 S1 126.58(13) . . ? C11 C12 C7 121.08(15) . . ? C25 C24 H24 119.8 . . ? C25 C24 C23 120.37(18) . . ? C23 C24 H24 119.8 . . ? C6 C5 H5 120.3 . . ? C4 C5 C6 119.44(16) . . ? C4 C5 H5 120.3 . . ? C12 C11 H11 120.6 . . ? C10 C11 C12 118.76(15) . . ? C10 C11 H11 120.6 . . ? C2 C1 S1 125.99(13) . . ? C2 C1 C6 121.79(16) . . ? C6 C1 S1 112.20(13) . . ? C2 C3 H3 119.4 . . ? C2 C3 C4 121.16(16) . . ? C4 C3 H3 119.4 . . ? C21 C22 H22 119.9 . . ? C21 C22 C23 120.19(17) . . ? C23 C22 H22 119.9 . . ? C9 C10 H10 119.4 . . ? C11 C10 C9 121.22(16) . . ? C11 C10 H10 119.4 . . ? C5 C4 C3 120.43(16) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? N1 C15 C14 123.29(17) . . ? N1 C15 H15 118.4 . . ? C14 C15 H15 118.4 . . ? C24 C23 H23 120.2 . . ? C22 C23 C24 119.66(17) . . ? C22 C23 H23 120.2 . . ? 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 S1 C12 1.7467(17) . ? S1 C1 1.7570(17) . ? F2 C18 1.338(2) . ? F1 C18 1.337(2) . ? O1 C19 1.214(2) . ? F3 C18 1.339(2) . ? N1 C16 1.337(2) . ? N1 C15 1.331(3) . ? C8 H8 0.9500 . ? C8 C9 1.395(2) . ? C8 C7 1.390(2) . ? C20 C19 1.485(2) . ? C20 C25 1.399(2) . ? C20 C21 1.397(2) . ? C19 C17 1.519(2) . ? C17 C13 1.410(2) . ? C17 C16 1.391(2) . ? C25 H25 0.9500 . ? C25 C24 1.377(3) . ? C13 C9 1.484(2) . ? C13 C14 1.395(2) . ? C9 C10 1.405(2) . ? C18 C16 1.513(3) . ? C21 H21 0.9500 . ? C21 C22 1.386(3) . ? C2 H2 0.9500 . ? C2 C1 1.392(2) . ? C2 C3 1.384(3) . ? C7 C6 1.450(2) . ? C7 C12 1.412(2) . ? C6 C5 1.397(2) . ? C6 C1 1.404(2) . ? C14 H14 0.9500 . ? C14 C15 1.378(3) . ? C12 C11 1.392(2) . ? C24 H24 0.9500 . ? C24 C23 1.395(3) . ? C5 H5 0.9500 . ? C5 C4 1.389(2) . ? C11 H11 0.9500 . ? C11 C10 1.377(2) . ? C3 H3 0.9500 . ? C3 C4 1.397(3) . ? C22 H22 0.9500 . ? C22 C23 1.391(3) . ? C10 H10 0.9500 . ? C4 H4 0.9500 . ? C15 H15 0.9500 . ? C23 H23 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 S1 C12 C11 C10 -178.79(14) . . . . ? F2 C18 C16 N1 -163.57(15) . . . . ? F2 C18 C16 C17 15.9(2) . . . . ? F1 C18 C16 N1 -43.7(2) . . . . ? F1 C18 C16 C17 135.80(17) . . . . ? O1 C19 C17 C13 -101.29(18) . . . . ? O1 C19 C17 C16 79.1(2) . . . . ? F3 C18 C16 N1 75.91(19) . . . . ? F3 C18 C16 C17 -104.64(19) . . . . ? C8 C9 C10 C11 0.0(3) . . . . ? C8 C7 C6 C5 0.8(3) . . . . ? C8 C7 C6 C1 -178.09(17) . . . . ? C8 C7 C12 S1 179.83(13) . . . . ? C8 C7 C12 C11 1.2(3) . . . . ? C20 C19 C17 C13 79.80(19) . . . . ? C20 C19 C17 C16 -99.76(18) . . . . ? C20 C25 C24 C23 -0.8(3) . . . . ? C20 C21 C22 C23 0.2(3) . . . . ? C19 C20 C25 C24 -176.97(16) . . . . ? C19 C20 C21 C22 177.22(16) . . . . ? C19 C17 C13 C9 -0.5(2) . . . . ? C19 C17 C13 C14 -178.66(15) . . . . ? C19 C17 C16 N1 180.00(16) . . . . ? C19 C17 C16 C18 0.6(3) . . . . ? C17 C13 C9 C8 47.8(2) . . . . ? C17 C13 C9 C10 -133.00(18) . . . . ? C17 C13 C14 C15 -1.3(3) . . . . ? C25 C20 C19 O1 0.0(2) . . . . ? C25 C20 C19 C17 178.89(15) . . . . ? C25 C20 C21 C22 -0.8(3) . . . . ? C25 C24 C23 C22 0.2(3) . . . . ? C13 C17 C16 N1 0.4(3) . . . . ? C13 C17 C16 C18 -178.95(16) . . . . ? C13 C9 C10 C11 -179.20(16) . . . . ? C13 C14 C15 N1 0.3(3) . . . . ? C9 C8 C7 C6 177.21(16) . . . . ? C9 C8 C7 C12 -1.4(2) . . . . ? C9 C13 C14 C15 -179.48(16) . . . . ? C21 C20 C19 O1 -178.02(16) . . . . ? C21 C20 C19 C17 0.9(2) . . . . ? C21 C20 C25 C24 1.1(3) . . . . ? C21 C22 C23 C24 0.1(3) . . . . ? C2 C3 C4 C5 -1.2(3) . . . . ? C7 C8 C9 C13 -179.97(16) . . . . ? C7 C8 C9 C10 0.8(2) . . . . ? C7 C6 C5 C4 -177.31(16) . . . . ? C7 C6 C1 S1 -1.93(18) . . . . ? C7 C6 C1 C2 176.92(15) . . . . ? C7 C12 C11 C10 -0.3(3) . . . . ? C16 N1 C15 C14 1.1(3) . . . . ? C16 C17 C13 C9 179.10(15) . . . . ? C16 C17 C13 C14 0.9(2) . . . . ? C6 C7 C12 S1 1.00(18) . . . . ? C6 C7 C12 C11 -177.66(16) . . . . ? C6 C5 C4 C3 0.1(3) . . . . ? C14 C13 C9 C8 -134.10(18) . . . . ? C14 C13 C9 C10 45.1(2) . . . . ? C12 S1 C1 C2 -176.68(16) . . . . ? C12 S1 C1 C6 2.12(14) . . . . ? C12 C7 C6 C5 179.44(17) . . . . ? C12 C7 C6 C1 0.6(2) . . . . ? C12 C11 C10 C9 -0.3(3) . . . . ? C5 C6 C1 S1 179.10(13) . . . . ? C5 C6 C1 C2 -2.0(3) . . . . ? C1 S1 C12 C7 -1.77(14) . . . . ? C1 S1 C12 C11 176.80(17) . . . . ? C1 C2 C3 C4 0.7(3) . . . . ? C1 C6 C5 C4 1.5(2) . . . . ? C3 C2 C1 S1 179.66(14) . . . . ? C3 C2 C1 C6 1.0(3) . . . . ? C15 N1 C16 C17 -1.4(3) . . . . ? C15 N1 C16 C18 178.02(16) . . . . ? 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 -0.7829 -16.1421 1.1115 -0.7014 -0.3865 0.5989 1.0060 16.2877 -0.3473 0.7663 0.4212 -0.4852 1.6579 1.2720 5.6333 0.4880 0.2610 0.8329 -1.7055 -2.2020 -5.5781 -0.5291 -0.2836 -0.7997 0.9632 -16.3220 0.2507 -0.5099 -0.6724 0.5366 -0.0103 -7.7164 -5.2916 -0.5117 -0.6646 -0.5445 -0.9718 16.2991 -0.3653 0.5034 0.6641 -0.5528 -4.1431 -0.6671 3.9521 -0.4241 0.7826 0.4557 -4.9707 6.3613 -0.6462 -0.4326 0.7876 -0.4387 5.1468 -3.7223 -1.4858 0.4784 -0.8761 0.0601