#------------------------------------------------------------------------------ #$Date: 2024-12-17 04:09:21 +0200 (Tue, 17 Dec 2024) $ #$Revision: 296887 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/96/7249697.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_7249697 loop_ _publ_author_name 'Sato, Kazuyuki' 'Kuroki, Tomohiro' 'Minami, Haruka' 'Sato, Azusa' 'Karuo, Yukiko' 'Tarui, Atsushi' 'Kawai, Kentaro' 'Omote, Masaaki' _publ_section_title ; Electrophilic aromatic substitution using fluorinated isoxazolines at the C5 position via C--F bond cleavage ; _journal_issue 53 _journal_name_full 'RSC Advances' _journal_page_first 39543 _journal_page_last 39549 _journal_paper_doi 10.1039/D4RA07102F _journal_volume 14 _journal_year 2024 _chemical_formula_moiety 'C23 H19 F2 N O' _chemical_formula_sum 'C23 H19 F2 N O' _chemical_formula_weight 363.39 _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 2024-04-18 _audit_creation_method ; Olex2 1.5-ac5-024 (compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498) ; _audit_update_record ; 2024-04-19 deposited with the CCDC. 2024-12-11 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.2100(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 17.3894(2) _cell_length_b 6.21370(10) _cell_length_c 16.7372(2) _cell_measurement_reflns_used 19760 _cell_measurement_temperature 120.0(4) _cell_measurement_theta_max 76.6980 _cell_measurement_theta_min 2.5370 _cell_volume 1797.88(4) _computing_cell_refinement 'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)' _computing_data_collection 'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)' _computing_data_reduction 'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)' _computing_molecular_graphics 'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 120.0(4) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.996 _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 6.00 34.00 0.50 0.10 -- 43.16 94.00-119.85 56 2 \w 21.00 117.00 0.50 0.10 -- 43.16 57.00-150.00 192 3 \w 21.00 117.00 0.50 0.10 -- 43.16 57.00 -60.00 192 4 \w 6.00 34.00 0.50 0.10 -- 43.16 94.00 11.65 56 5 \w 9.00 42.00 0.50 0.10 -- 43.16 89.00 130.21 66 6 \w -31.00 123.00 0.50 0.10 -- 43.16 8.00-124.00 308 7 \w 38.00 106.00 0.50 0.39 -- 113.00 -95.00 0.00 136 8 \w 19.00 95.00 0.50 0.10 -- 43.16-125.00 -60.00 152 9 \w 19.00 95.00 0.50 0.10 -- 43.16-125.00-150.00 152 10 \w 41.00 112.00 0.50 0.39 -- 113.00-125.00 -30.00 142 11 \w 41.00 112.00 0.50 0.39 -- 113.00-125.00 0.00 142 12 \w 41.00 112.00 0.50 0.39 -- 113.00-125.00 60.00 142 13 \w 41.00 112.00 0.50 0.39 -- 113.00-125.00 150.00 142 14 \w 41.00 112.00 0.50 0.39 -- 113.00-125.00 90.00 142 15 \w 41.00 112.00 0.50 0.39 -- 113.00-125.00-150.00 142 16 \w 39.00 109.00 0.50 0.39 -- 113.00 -78.00-125.72 140 17 \w 39.00 76.00 0.50 0.39 -- 113.00 -61.00-150.00 74 18 \w 39.00 106.00 0.50 0.39 -- 113.00 -77.00 -60.00 134 19 \w 39.00 76.00 0.50 0.39 -- 113.00 -61.00 0.00 74 20 \w 39.00 76.00 0.50 0.39 -- 113.00 -61.00 -30.00 74 21 \w 39.00 76.00 0.50 0.39 -- 113.00 -61.00-120.00 74 22 \w 39.00 106.00 0.50 0.39 -- 113.00 -77.00 30.00 134 23 \w 39.00 76.00 0.50 0.39 -- 113.00 -61.00 60.00 74 24 \w 39.00 76.00 0.50 0.39 -- 113.00 -61.00 120.00 74 25 \w 39.00 76.00 0.50 0.39 -- 113.00 -61.00 150.00 74 26 \w -36.00 35.00 0.50 0.10 -- 43.16 -19.00 60.00 142 27 \w 37.00 178.00 0.50 0.39 -- 113.00 8.00-124.00 282 28 \w 90.00 178.00 0.50 0.39 -- 113.00 61.00-150.00 176 29 \w 91.00 178.00 0.50 0.39 -- 113.00 45.00-120.00 174 30 \w 91.00 178.00 0.50 0.39 -- 113.00 45.00 -90.00 174 31 \w 63.00 178.00 0.50 0.39 -- 113.00 15.00 0.00 230 32 \w 63.00 178.00 0.50 0.39 -- 113.00 15.00 120.00 230 33 \w 63.00 178.00 0.50 0.39 -- 113.00 15.00 150.00 230 34 \w 91.00 178.00 0.50 0.39 -- 113.00 45.00 120.00 174 35 \w 86.00 178.00 0.50 0.39 -- 113.00 83.00 157.40 184 36 \w 86.00 178.00 0.50 0.39 -- 113.00 90.00 57.81 184 37 \w 80.00 178.00 0.50 0.39 -- 113.00 125.00 -30.00 196 38 \w 90.00 178.00 0.50 0.39 -- 113.00 95.00 -52.27 176 39 \w 80.00 178.00 0.50 0.39 -- 113.00 125.00-180.00 196 40 \w -123.00 33.00 0.50 0.10 -- -43.16 -8.00 60.00 312 41 \w -120.00 -20.00 0.50 0.10 -- -43.16 -38.00 -30.00 200 42 \w -174.00 -81.00 0.50 0.39 -- -104.50 -77.00 0.00 186 43 \w -174.00 -75.00 0.50 0.39 -- -104.50 -77.00 30.00 198 44 \w -117.00 -14.00 0.50 0.10 -- -43.16 -77.00 90.00 206 45 \w -174.00 -75.00 0.50 0.39 -- -104.50 -77.00 67.24 198 46 \w -174.00 -28.00 0.50 0.39 -- -104.50 -8.00 60.00 292 47 \w -66.00 -30.00 0.50 0.39 -- -104.50 61.00 120.00 72 48 \w -96.00 -30.00 0.50 0.39 -- -104.50 77.00 60.00 132 49 \w -66.00 -30.00 0.50 0.39 -- -104.50 61.00 0.00 72 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy R, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0130187000 _diffrn_orient_matrix_UB_12 0.0228639000 _diffrn_orient_matrix_UB_13 -0.0892020000 _diffrn_orient_matrix_UB_21 -0.0879479000 _diffrn_orient_matrix_UB_22 -0.0137651000 _diffrn_orient_matrix_UB_23 -0.0238312000 _diffrn_orient_matrix_UB_31 -0.0061316000 _diffrn_orient_matrix_UB_32 0.2464903000 _diffrn_orient_matrix_UB_33 0.0068573000 _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 0.0373 _diffrn_reflns_av_unetI/netI 0.0184 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 40254 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 78.006 _diffrn_reflns_theta_min 2.556 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'PhotonJet R (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.791 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.79248 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023) 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 1.343 _exptl_crystal_description block _exptl_crystal_F_000 760 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: hexane and ethylacetate' _exptl_crystal_size_max 0.096 _exptl_crystal_size_mid 0.083 _exptl_crystal_size_min 0.051 _refine_diff_density_max 0.256 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.039 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 246 _refine_ls_number_reflns 3825 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.078 _refine_ls_R_factor_all 0.0404 _refine_ls_R_factor_gt 0.0379 _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^)+(0.0345P)^2^+0.7896P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0895 _refine_ls_wR_factor_ref 0.0912 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3612 _reflns_number_total 3825 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ra07102f2.cif _cod_data_source_block x-1339_auto _cod_database_code 7249697 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C23 H19 F2 N O' _chemical_oxdiff_usercomment 5aH _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: C2(H2), C3(H3), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23) 2.b Idealised Me refined as rotating group: C26(H26C,H26A,H26B), C27(H27A,H27C,H27B) ; _shelx_res_file ; TITL x-1339_auto_a.res in P2(1)/c x-1339_auto.res created by SHELXL-2018/3 at 14:53:32 on 18-Apr-2024 REM Old TITL X-1339_auto in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.111, Rweak 0.039, Alpha 0.019 REM 0.874 for 356 systematic absences, Orientation as input REM Formula found by SHELXT: C23 N O F25 CELL 1.54184 17.3894 6.2137 16.7372 90 96.21 90 ZERR 4 0.0002 0.0001 0.0002 0 0.001 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F N O UNIT 92 76 8 4 4 L.S. 30 PLAN 5 TEMP -153 CONF BOND $H HTAB fmap 2 acta REM REM REM WGHT 0.034500 0.789600 FVAR 0.38873 C1 1 0.634083 0.482155 0.666236 11.00000 0.02621 0.02457 = 0.01869 0.00114 0.00419 -0.00033 C2 1 0.609795 0.681349 0.691888 11.00000 0.03145 0.02561 = 0.02397 -0.00235 0.00237 -0.00023 AFIX 43 H2 2 0.646168 0.779990 0.717638 11.00000 -1.20000 AFIX 0 C3 1 0.531566 0.734903 0.679455 11.00000 0.03414 0.02761 = 0.02542 -0.00093 0.00598 0.00615 AFIX 43 H3 2 0.515122 0.870232 0.697831 11.00000 -1.20000 AFIX 0 C4 1 0.477038 0.596050 0.640986 11.00000 0.02792 0.03176 = 0.02465 0.00435 0.00562 0.00202 C5 1 0.501649 0.396084 0.613803 11.00000 0.02809 0.02991 = 0.02360 0.00322 0.00357 -0.00200 C6 1 0.579643 0.342238 0.627129 11.00000 0.02912 0.02357 = 0.02363 -0.00031 0.00503 -0.00049 AFIX 43 H6 2 0.596259 0.206684 0.609132 11.00000 -1.20000 AFIX 0 C7 1 0.828766 0.330690 0.760241 11.00000 0.02914 0.02177 = 0.01826 0.00177 0.00548 0.00045 N8 4 0.798142 0.151680 0.735361 11.00000 0.03081 0.02256 = 0.02612 0.00260 0.00120 0.00113 O9 5 0.724995 0.189693 0.692130 11.00000 0.02873 0.01860 = 0.02778 0.00121 0.00149 -0.00196 C10 1 0.718615 0.417757 0.671878 11.00000 0.02774 0.01711 = 0.02061 -0.00039 0.00391 -0.00018 C11 1 0.773758 0.514748 0.740218 11.00000 0.02810 0.02032 = 0.02013 -0.00042 0.00489 -0.00060 C12 1 0.905158 0.343046 0.807054 11.00000 0.02762 0.02734 = 0.01877 0.00390 0.00589 0.00069 C13 1 0.954481 0.164342 0.811061 11.00000 0.03327 0.03192 = 0.02489 0.00363 0.00759 0.00491 AFIX 43 H13 2 0.939571 0.037349 0.781786 11.00000 -1.20000 AFIX 0 C14 1 1.025320 0.173641 0.858050 11.00000 0.03244 0.04400 = 0.03387 0.00970 0.00785 0.01059 AFIX 43 H14 2 1.058606 0.051995 0.861436 11.00000 -1.20000 AFIX 0 C15 1 1.047680 0.360040 0.900099 11.00000 0.02842 0.05393 = 0.02909 0.00774 -0.00079 -0.00138 AFIX 43 H15 2 1.096133 0.365302 0.932251 11.00000 -1.20000 AFIX 0 C16 1 0.999634 0.538082 0.895321 11.00000 0.03457 0.04145 = 0.02593 0.00038 0.00129 -0.00595 AFIX 43 H16 2 1.015358 0.665753 0.923759 11.00000 -1.20000 AFIX 0 C17 1 0.928491 0.530353 0.849027 11.00000 0.03139 0.03037 = 0.02306 0.00157 0.00404 -0.00025 AFIX 43 H17 2 0.895573 0.652768 0.845874 11.00000 -1.20000 AFIX 0 C18 1 0.751332 0.454228 0.591151 11.00000 0.02311 0.02427 = 0.01996 -0.00214 0.00189 -0.00232 C19 1 0.789895 0.290744 0.554952 11.00000 0.03292 0.02688 = 0.02587 -0.00348 0.00589 0.00097 AFIX 43 H19 2 0.797600 0.155060 0.580737 11.00000 -1.20000 AFIX 0 C20 1 0.817140 0.326394 0.480936 11.00000 0.03795 0.03939 = 0.02896 -0.00960 0.01174 -0.00085 AFIX 43 H20 2 0.843544 0.214716 0.456354 11.00000 -1.20000 AFIX 0 C21 1 0.806077 0.522923 0.442950 11.00000 0.03431 0.04577 = 0.02181 -0.00432 0.00869 -0.01054 AFIX 43 H21 2 0.824232 0.545530 0.392079 11.00000 -1.20000 AFIX 0 C22 1 0.768443 0.687335 0.479098 11.00000 0.03215 0.03390 = 0.02400 0.00404 0.00080 -0.00787 AFIX 43 H22 2 0.761288 0.823105 0.453265 11.00000 -1.20000 AFIX 0 C23 1 0.741220 0.653346 0.553101 11.00000 0.02623 0.02586 = 0.02337 -0.00021 0.00221 -0.00159 AFIX 43 H23 2 0.715609 0.766257 0.577878 11.00000 -1.20000 AFIX 0 F24 3 0.807485 0.699731 0.720146 11.00000 0.03550 0.01756 = 0.02999 0.00114 -0.00225 -0.00392 F25 3 0.737800 0.561209 0.807260 11.00000 0.03358 0.03749 = 0.02053 -0.00661 0.00434 0.00531 C26 1 0.445076 0.242297 0.569842 11.00000 0.02948 0.03536 = 0.04406 -0.00205 -0.00121 -0.00341 AFIX 137 H26C 2 0.471736 0.108246 0.558931 11.00000 -1.50000 H26A 2 0.423374 0.307196 0.518974 11.00000 -1.50000 H26B 2 0.403286 0.211323 0.603000 11.00000 -1.50000 AFIX 0 C27 1 0.392741 0.658954 0.628607 11.00000 0.02939 0.04111 = 0.04278 0.00211 0.00627 0.00458 AFIX 137 H27A 2 0.375292 0.662335 0.570951 11.00000 -1.50000 H27C 2 0.386161 0.801749 0.651780 11.00000 -1.50000 H27B 2 0.362045 0.553615 0.655054 11.00000 -1.50000 AFIX 0 HKLF 4 REM x-1339_auto_a.res in P2(1)/c REM wR2 = 0.0912, GooF = S = 1.078, Restrained GooF = 1.078 for all data REM R1 = 0.0379 for 3612 Fo > 4sig(Fo) and 0.0404 for all 3825 data REM 246 parameters refined using 0 restraints END WGHT 0.0345 0.7896 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.256, deepest hole -0.253, 1-sigma level 0.039 Q1 1 0.6727 0.4567 0.6731 11.00000 0.05 0.26 Q2 1 0.8103 0.4307 0.7521 11.00000 0.05 0.23 Q3 1 0.8664 0.3404 0.7843 11.00000 0.05 0.22 Q4 1 0.7403 0.4790 0.7039 11.00000 0.05 0.20 Q5 1 0.7354 0.4422 0.6299 11.00000 0.05 0.19 ; _shelx_res_checksum 41792 _olex2_exptl_crystal_mounting_method 'The crystal was mounted on a MiTeGEN Dual Thickness MicroLoops in perfluoropolyether oil' _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 1.515 _oxdiff_exptl_absorpt_empirical_full_min 0.755 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 C1 C 0.63408(7) 0.4822(2) 0.66624(7) 0.0230(2) Uani 1 1 d . . . . . C2 C 0.60980(7) 0.6813(2) 0.69189(7) 0.0271(3) Uani 1 1 d . . . . . H2 H 0.646168 0.779990 0.717638 0.032 Uiso 1 1 calc R U . . . C3 C 0.53157(8) 0.7349(2) 0.67946(7) 0.0289(3) Uani 1 1 d . . . . . H3 H 0.515122 0.870232 0.697831 0.035 Uiso 1 1 calc R U . . . C4 C 0.47704(7) 0.5961(2) 0.64099(7) 0.0279(3) Uani 1 1 d . . . . . C5 C 0.50165(7) 0.3961(2) 0.61380(7) 0.0271(3) Uani 1 1 d . . . . . C6 C 0.57964(7) 0.3422(2) 0.62713(7) 0.0253(2) Uani 1 1 d . . . . . H6 H 0.596259 0.206684 0.609132 0.030 Uiso 1 1 calc R U . . . C7 C 0.82877(7) 0.33069(19) 0.76024(7) 0.0228(2) Uani 1 1 d . . . . . N8 N 0.79814(6) 0.15168(17) 0.73536(6) 0.0266(2) Uani 1 1 d . . . . . O9 O 0.72499(5) 0.18969(13) 0.69213(5) 0.02515(19) Uani 1 1 d . . . . . C10 C 0.71862(7) 0.41776(18) 0.67188(7) 0.0217(2) Uani 1 1 d . . . . . C11 C 0.77376(7) 0.51475(19) 0.74022(7) 0.0227(2) Uani 1 1 d . . . . . C12 C 0.90516(7) 0.3430(2) 0.80705(7) 0.0243(2) Uani 1 1 d . . . . . C13 C 0.95448(8) 0.1643(2) 0.81106(7) 0.0297(3) Uani 1 1 d . . . . . H13 H 0.939571 0.037349 0.781786 0.036 Uiso 1 1 calc R U . . . C14 C 1.02532(8) 0.1736(3) 0.85805(8) 0.0365(3) Uani 1 1 d . . . . . H14 H 1.058606 0.051995 0.861436 0.044 Uiso 1 1 calc R U . . . C15 C 1.04768(8) 0.3600(3) 0.90010(8) 0.0374(3) Uani 1 1 d . . . . . H15 H 1.096133 0.365302 0.932251 0.045 Uiso 1 1 calc R U . . . C16 C 0.99963(8) 0.5381(2) 0.89532(8) 0.0341(3) Uani 1 1 d . . . . . H16 H 1.015358 0.665753 0.923759 0.041 Uiso 1 1 calc R U . . . C17 C 0.92849(7) 0.5304(2) 0.84903(7) 0.0282(3) Uani 1 1 d . . . . . H17 H 0.895573 0.652768 0.845874 0.034 Uiso 1 1 calc R U . . . C18 C 0.75133(7) 0.45423(19) 0.59115(7) 0.0225(2) Uani 1 1 d . . . . . C19 C 0.78990(7) 0.2907(2) 0.55495(7) 0.0284(3) Uani 1 1 d . . . . . H19 H 0.797600 0.155060 0.580737 0.034 Uiso 1 1 calc R U . . . C20 C 0.81714(8) 0.3264(2) 0.48094(8) 0.0348(3) Uani 1 1 d . . . . . H20 H 0.843544 0.214716 0.456354 0.042 Uiso 1 1 calc R U . . . C21 C 0.80608(8) 0.5229(2) 0.44295(8) 0.0336(3) Uani 1 1 d . . . . . H21 H 0.824232 0.545530 0.392079 0.040 Uiso 1 1 calc R U . . . C22 C 0.76844(7) 0.6873(2) 0.47910(7) 0.0302(3) Uani 1 1 d . . . . . H22 H 0.761288 0.823105 0.453265 0.036 Uiso 1 1 calc R U . . . C23 C 0.74122(7) 0.6533(2) 0.55310(7) 0.0252(2) Uani 1 1 d . . . . . H23 H 0.715609 0.766257 0.577878 0.030 Uiso 1 1 calc R U . . . F24 F 0.80748(4) 0.69973(11) 0.72015(4) 0.02811(17) Uani 1 1 d . . . . . F25 F 0.73780(4) 0.56121(13) 0.80726(4) 0.03043(18) Uani 1 1 d . . . . . C26 C 0.44508(8) 0.2423(2) 0.56984(9) 0.0367(3) Uani 1 1 d . . . . . H26C H 0.471736 0.108246 0.558931 0.055 Uiso 1 1 calc R U . . . H26A H 0.423374 0.307196 0.518974 0.055 Uiso 1 1 calc R U . . . H26B H 0.403286 0.211323 0.603000 0.055 Uiso 1 1 calc R U . . . C27 C 0.39274(8) 0.6590(3) 0.62861(9) 0.0376(3) Uani 1 1 d . . . . . H27A H 0.375292 0.662335 0.570951 0.056 Uiso 1 1 calc R U . . . H27C H 0.386161 0.801749 0.651780 0.056 Uiso 1 1 calc R U . . . H27B H 0.362045 0.553615 0.655054 0.056 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 C1 0.0262(6) 0.0246(6) 0.0187(5) 0.0011(4) 0.0042(4) -0.0003(5) C2 0.0315(6) 0.0256(6) 0.0240(6) -0.0023(5) 0.0024(5) -0.0002(5) C3 0.0341(6) 0.0276(6) 0.0254(6) -0.0009(5) 0.0060(5) 0.0062(5) C4 0.0279(6) 0.0318(7) 0.0247(6) 0.0043(5) 0.0056(5) 0.0020(5) C5 0.0281(6) 0.0299(6) 0.0236(6) 0.0032(5) 0.0036(5) -0.0020(5) C6 0.0291(6) 0.0236(6) 0.0236(5) -0.0003(5) 0.0050(5) -0.0005(5) C7 0.0291(6) 0.0218(6) 0.0183(5) 0.0018(4) 0.0055(4) 0.0005(5) N8 0.0308(5) 0.0226(5) 0.0261(5) 0.0026(4) 0.0012(4) 0.0011(4) O9 0.0287(4) 0.0186(4) 0.0278(4) 0.0012(3) 0.0015(3) -0.0020(3) C10 0.0277(6) 0.0171(5) 0.0206(5) -0.0004(4) 0.0039(4) -0.0002(4) C11 0.0281(6) 0.0203(6) 0.0201(5) -0.0004(4) 0.0049(4) -0.0006(5) C12 0.0276(6) 0.0273(6) 0.0188(5) 0.0039(4) 0.0059(4) 0.0007(5) C13 0.0333(6) 0.0319(7) 0.0249(6) 0.0036(5) 0.0076(5) 0.0049(5) C14 0.0324(7) 0.0440(8) 0.0339(7) 0.0097(6) 0.0079(5) 0.0106(6) C15 0.0284(6) 0.0539(9) 0.0291(6) 0.0077(6) -0.0008(5) -0.0014(6) C16 0.0346(7) 0.0414(8) 0.0259(6) 0.0004(6) 0.0013(5) -0.0059(6) C17 0.0314(6) 0.0304(6) 0.0231(6) 0.0016(5) 0.0040(5) -0.0003(5) C18 0.0231(5) 0.0243(6) 0.0200(5) -0.0021(4) 0.0019(4) -0.0023(4) C19 0.0329(6) 0.0269(6) 0.0259(6) -0.0035(5) 0.0059(5) 0.0010(5) C20 0.0379(7) 0.0394(8) 0.0290(6) -0.0096(6) 0.0117(5) -0.0009(6) C21 0.0343(7) 0.0458(8) 0.0218(6) -0.0043(5) 0.0087(5) -0.0105(6) C22 0.0321(6) 0.0339(7) 0.0240(6) 0.0040(5) 0.0008(5) -0.0079(5) C23 0.0262(6) 0.0259(6) 0.0234(6) -0.0002(5) 0.0022(4) -0.0016(5) F24 0.0355(4) 0.0176(3) 0.0300(4) 0.0011(3) -0.0022(3) -0.0039(3) F25 0.0336(4) 0.0375(4) 0.0205(3) -0.0066(3) 0.0043(3) 0.0053(3) C26 0.0295(6) 0.0354(7) 0.0441(8) -0.0021(6) -0.0012(6) -0.0034(6) C27 0.0294(7) 0.0411(8) 0.0428(8) 0.0021(6) 0.0063(6) 0.0046(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_ _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 C2 C1 C6 119.09(11) . . ? C2 C1 C10 122.71(11) . . ? C6 C1 C10 117.95(11) . . ? C1 C2 H2 120.3 . . ? C1 C2 C3 119.37(12) . . ? C3 C2 H2 120.3 . . ? C2 C3 H3 119.1 . . ? C4 C3 C2 121.84(12) . . ? C4 C3 H3 119.1 . . ? C3 C4 C5 118.88(11) . . ? C3 C4 C27 120.48(12) . . ? C5 C4 C27 120.63(12) . . ? C4 C5 C26 120.90(12) . . ? C6 C5 C4 119.10(12) . . ? C6 C5 C26 119.99(12) . . ? C1 C6 H6 119.1 . . ? C5 C6 C1 121.71(12) . . ? C5 C6 H6 119.1 . . ? N8 C7 C11 110.79(10) . . ? N8 C7 C12 122.54(11) . . ? C12 C7 C11 126.52(11) . . ? C7 N8 O9 109.89(10) . . ? N8 O9 C10 108.84(8) . . ? C1 C10 C11 117.79(10) . . ? C1 C10 C18 110.76(9) . . ? O9 C10 C1 108.64(9) . . ? O9 C10 C11 100.53(9) . . ? O9 C10 C18 108.73(9) . . ? C11 C10 C18 109.65(9) . . ? C7 C11 C10 101.44(9) . . ? F24 C11 C7 114.82(10) . . ? F24 C11 C10 113.73(9) . . ? F24 C11 F25 105.84(9) . . ? F25 C11 C7 108.20(9) . . ? F25 C11 C10 112.88(9) . . ? C13 C12 C7 119.86(11) . . ? C17 C12 C7 120.55(11) . . ? C17 C12 C13 119.58(12) . . ? C12 C13 H13 120.2 . . ? C14 C13 C12 119.68(13) . . ? C14 C13 H13 120.2 . . ? C13 C14 H14 119.9 . . ? C15 C14 C13 120.27(13) . . ? C15 C14 H14 119.9 . . ? C14 C15 H15 119.9 . . ? C16 C15 C14 120.22(13) . . ? C16 C15 H15 119.9 . . ? C15 C16 H16 120.0 . . ? C15 C16 C17 120.06(14) . . ? C17 C16 H16 120.0 . . ? C12 C17 H17 119.9 . . ? C16 C17 C12 120.17(13) . . ? C16 C17 H17 119.9 . . ? C19 C18 C10 121.08(11) . . ? C19 C18 C23 119.47(11) . . ? C23 C18 C10 119.45(10) . . ? C18 C19 H19 120.1 . . ? C20 C19 C18 119.87(12) . . ? C20 C19 H19 120.1 . . ? C19 C20 H20 119.8 . . ? C21 C20 C19 120.47(12) . . ? C21 C20 H20 119.8 . . ? C20 C21 H21 120.0 . . ? C20 C21 C22 119.96(12) . . ? C22 C21 H21 120.0 . . ? C21 C22 H22 120.0 . . ? C21 C22 C23 119.96(12) . . ? C23 C22 H22 120.0 . . ? C18 C23 H23 119.9 . . ? C22 C23 C18 120.26(12) . . ? C22 C23 H23 119.9 . . ? C5 C26 H26C 109.5 . . ? C5 C26 H26A 109.5 . . ? C5 C26 H26B 109.5 . . ? H26C C26 H26A 109.5 . . ? H26C C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C4 C27 H27A 109.5 . . ? C4 C27 H27C 109.5 . . ? C4 C27 H27B 109.5 . . ? H27A C27 H27C 109.5 . . ? H27A C27 H27B 109.5 . . ? H27C C27 H27B 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 C1 C2 1.3907(17) . ? C1 C6 1.3951(17) . ? C1 C10 1.5165(16) . ? C2 H2 0.9500 . ? C2 C3 1.3940(18) . ? C3 H3 0.9500 . ? C3 C4 1.3878(19) . ? C4 C5 1.4058(18) . ? C4 C27 1.5096(18) . ? C5 C6 1.3913(17) . ? C5 C26 1.5052(18) . ? C6 H6 0.9500 . ? C7 N8 1.2831(16) . ? C7 C11 1.5053(16) . ? C7 C12 1.4695(16) . ? N8 O9 1.4136(13) . ? O9 C10 1.4585(14) . ? C10 C11 1.5342(16) . ? C10 C18 1.5385(15) . ? C11 F24 1.3493(13) . ? C11 F25 1.3730(13) . ? C12 C13 1.4003(17) . ? C12 C17 1.3968(18) . ? C13 H13 0.9500 . ? C13 C14 1.3891(19) . ? C14 H14 0.9500 . ? C14 C15 1.389(2) . ? C15 H15 0.9500 . ? C15 C16 1.383(2) . ? C16 H16 0.9500 . ? C16 C17 1.3877(18) . ? C17 H17 0.9500 . ? C18 C19 1.3916(17) . ? C18 C23 1.3939(17) . ? C19 H19 0.9500 . ? C19 C20 1.3911(18) . ? C20 H20 0.9500 . ? C20 C21 1.381(2) . ? C21 H21 0.9500 . ? C21 C22 1.387(2) . ? C22 H22 0.9500 . ? C22 C23 1.3891(17) . ? C23 H23 0.9500 . ? C26 H26C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C27 H27A 0.9800 . ? C27 H27C 0.9800 . ? C27 H27B 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 C1 C2 C3 C4 -0.98(19) . . . . ? C1 C10 C11 C7 144.99(10) . . . . ? C1 C10 C11 F24 -91.17(12) . . . . ? C1 C10 C11 F25 29.43(14) . . . . ? C1 C10 C18 C19 -127.91(12) . . . . ? C1 C10 C18 C23 51.18(14) . . . . ? C2 C1 C6 C5 -0.59(18) . . . . ? C2 C1 C10 O9 143.18(11) . . . . ? C2 C1 C10 C11 29.87(16) . . . . ? C2 C1 C10 C18 -97.45(13) . . . . ? C2 C3 C4 C5 -0.08(19) . . . . ? C2 C3 C4 C27 179.91(12) . . . . ? C3 C4 C5 C6 0.79(17) . . . . ? C3 C4 C5 C26 -178.40(12) . . . . ? C4 C5 C6 C1 -0.47(18) . . . . ? C6 C1 C2 C3 1.30(17) . . . . ? C6 C1 C10 O9 -42.65(13) . . . . ? C6 C1 C10 C11 -155.97(10) . . . . ? C6 C1 C10 C18 76.72(13) . . . . ? C7 N8 O9 C10 15.34(12) . . . . ? C7 C12 C13 C14 -177.35(11) . . . . ? C7 C12 C17 C16 177.77(11) . . . . ? N8 C7 C11 C10 -20.74(12) . . . . ? N8 C7 C11 F24 -143.83(10) . . . . ? N8 C7 C11 F25 98.22(11) . . . . ? N8 C7 C12 C13 14.09(17) . . . . ? N8 C7 C12 C17 -164.61(11) . . . . ? N8 O9 C10 C1 -151.12(9) . . . . ? N8 O9 C10 C11 -26.84(11) . . . . ? N8 O9 C10 C18 88.25(10) . . . . ? O9 C10 C11 C7 27.25(10) . . . . ? O9 C10 C11 F24 151.08(9) . . . . ? O9 C10 C11 F25 -88.31(11) . . . . ? O9 C10 C18 C19 -8.59(15) . . . . ? O9 C10 C18 C23 170.49(10) . . . . ? C10 C1 C2 C3 175.40(11) . . . . ? C10 C1 C6 C5 -174.97(11) . . . . ? C10 C18 C19 C20 178.34(11) . . . . ? C10 C18 C23 C22 -178.18(11) . . . . ? C11 C7 N8 O9 4.34(13) . . . . ? C11 C7 C12 C13 -170.83(11) . . . . ? C11 C7 C12 C17 10.47(17) . . . . ? C11 C10 C18 C19 100.43(13) . . . . ? C11 C10 C18 C23 -80.49(13) . . . . ? C12 C7 N8 O9 -179.90(9) . . . . ? C12 C7 C11 C10 163.71(10) . . . . ? C12 C7 C11 F24 40.61(15) . . . . ? C12 C7 C11 F25 -77.34(13) . . . . ? C12 C13 C14 C15 -0.82(19) . . . . ? C13 C12 C17 C16 -0.93(18) . . . . ? C13 C14 C15 C16 -0.2(2) . . . . ? C14 C15 C16 C17 0.6(2) . . . . ? C15 C16 C17 C12 -0.06(19) . . . . ? C17 C12 C13 C14 1.36(18) . . . . ? C18 C10 C11 C7 -87.16(11) . . . . ? C18 C10 C11 F24 36.68(13) . . . . ? C18 C10 C11 F25 157.29(9) . . . . ? C18 C19 C20 C21 -0.1(2) . . . . ? C19 C18 C23 C22 0.92(18) . . . . ? C19 C20 C21 C22 0.8(2) . . . . ? C20 C21 C22 C23 -0.66(19) . . . . ? C21 C22 C23 C18 -0.21(18) . . . . ? C23 C18 C19 C20 -0.75(19) . . . . ? C26 C5 C6 C1 178.73(12) . . . . ? C27 C4 C5 C6 -179.19(12) . . . . ? C27 C4 C5 C26 1.61(18) . . . . ?