#------------------------------------------------------------------------------ #$Date: 2022-05-16 08:31:14 +0300 (Mon, 16 May 2022) $ #$Revision: 275434 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/22/1552226.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_1552226 loop_ _publ_author_name 'Zhao, Na' 'Li, Yan' 'Yang, Weiyao' 'Zhuang, Jiabao' 'Li, Yue' 'Li, Nan' _publ_section_title ; Multifunctional pyrazoline based AIEgens: real-time tracking and specific protein “fishing” of lipid droplets ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC03111A _journal_year 2019 _chemical_formula_moiety 'C22 H15 F5 N2' _chemical_formula_sum 'C22 H15 F5 N2' _chemical_formula_weight 402.36 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2019-02-27 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-05-20 deposited with the CCDC. 2019-08-14 downloaded from the CCDC. ; _cell_angle_alpha 100.865(3) _cell_angle_beta 91.711(3) _cell_angle_gamma 103.357(3) _cell_formula_units_Z 4 _cell_length_a 11.1225(4) _cell_length_b 12.8307(5) _cell_length_c 13.8928(5) _cell_measurement_reflns_used 12472 _cell_measurement_temperature 298 _cell_measurement_theta_max 71.7230 _cell_measurement_theta_min 4.0900 _cell_volume 1888.83(13) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 298 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0356 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.988 _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 7.00 107.00 1.00 1.00 -- 35.91 19.00 -60.00 100 2 \w -4.00 75.00 1.00 1.00 -- 35.91 -99.00 -30.00 79 3 \w 9.00 103.00 1.00 1.00 -- 35.91 77.00 -90.00 94 4 \w 56.00 108.00 1.00 1.00 -- 35.91 179.00-120.00 52 5 \w -35.00 65.00 1.00 1.00 -- 35.91 -19.00 90.00 100 6 \w 53.00 108.00 1.00 1.00 -- 35.91-179.00 -60.00 55 7 \w -4.00 75.00 1.00 1.00 -- 35.91 -99.00 150.00 79 8 \w -31.00 53.00 1.00 1.00 -- 35.91 -57.00-120.00 84 9 \w -4.00 75.00 1.00 1.00 -- 35.91 -99.00 120.00 79 10 \w 56.00 108.00 1.00 1.00 -- 35.91 179.00 60.00 52 11 \w -31.00 53.00 1.00 1.00 -- 35.91 -57.00 0.00 84 12 \w 87.00 178.00 1.00 1.00 -- 108.00 30.00 0.00 91 13 \w 41.00 125.00 1.00 1.00 -- 108.00 -59.00-150.00 84 14 \w 39.00 109.00 1.00 1.00 -- 108.00 -94.00-180.00 70 15 \w 40.00 125.00 1.00 1.00 -- 108.00 -45.00 120.00 85 16 \w 39.00 109.00 1.00 1.00 -- 108.00 -94.00 0.00 70 17 \w 40.00 125.00 1.00 1.00 -- 108.00 -45.00 -30.00 85 18 \w 40.00 125.00 1.00 1.00 -- 108.00 -45.00-150.00 85 19 \w 90.00 175.00 1.00 1.00 -- 108.00 61.00 150.00 85 20 \w 38.00 116.00 1.00 1.00 -- 108.00-111.00 120.00 78 21 \w 40.00 125.00 1.00 1.00 -- 108.00 -45.00 30.00 85 22 \w 38.00 116.00 1.00 1.00 -- 108.00-111.00 -60.00 78 23 \w 39.00 109.00 1.00 1.00 -- 108.00 -94.00 120.00 70 24 \w 39.00 177.00 1.00 1.00 -- 108.00 0.00 -30.00 138 25 \w 19.00 103.00 1.00 1.00 -- 35.91 57.00-120.00 84 26 \w 7.00 107.00 1.00 1.00 -- 35.91 19.00-180.00 100 27 \w 9.00 103.00 1.00 1.00 -- 35.91 77.00 120.00 94 28 \w 19.00 103.00 1.00 1.00 -- 35.91 57.00 90.00 84 29 \w 9.00 103.00 1.00 1.00 -- 35.91 77.00 30.00 94 30 \w 9.00 103.00 1.00 1.00 -- 35.91 77.00-180.00 94 31 \w 19.00 103.00 1.00 1.00 -- 35.91 57.00 30.00 84 32 \w 19.00 103.00 1.00 1.00 -- 35.91 57.00 -30.00 84 33 \w 9.00 103.00 1.00 1.00 -- 35.91 77.00 -30.00 94 34 \w -4.00 75.00 1.00 1.00 -- 35.91 -99.00-150.00 79 35 \w 91.00 176.00 1.00 1.00 -- 108.00 45.00 120.00 85 36 \w 91.00 176.00 1.00 1.00 -- 108.00 45.00 30.00 85 37 \w 87.00 178.00 1.00 1.00 -- 108.00 30.00-150.00 91 38 \w 81.00 176.00 1.00 1.00 -- 108.00 77.00 -90.00 95 39 \w 87.00 178.00 1.00 1.00 -- 108.00 30.00 90.00 91 40 \w 81.00 176.00 1.00 1.00 -- 108.00 77.00 30.00 95 41 \w 81.00 176.00 1.00 1.00 -- 108.00 77.00 -60.00 95 42 \w 81.00 176.00 1.00 1.00 -- 108.00 77.00-120.00 95 43 \w 81.00 176.00 1.00 1.00 -- 108.00 77.00 120.00 95 44 \w 81.00 176.00 1.00 1.00 -- 108.00 77.00-150.00 95 45 \w 9.00 103.00 1.00 1.00 -- 35.91 77.00 60.00 94 46 \w 17.00 105.00 1.00 1.00 -- 35.91 37.00 -30.00 88 47 \w 19.00 103.00 1.00 1.00 -- 35.91 57.00 -60.00 84 48 \w 17.00 105.00 1.00 1.00 -- 35.91 37.00-150.00 88 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0471714000 _diffrn_orient_matrix_UB_12 0.1007823000 _diffrn_orient_matrix_UB_13 -0.0127745000 _diffrn_orient_matrix_UB_21 -0.0927513000 _diffrn_orient_matrix_UB_22 -0.0216866000 _diffrn_orient_matrix_UB_23 0.0782955000 _diffrn_orient_matrix_UB_31 0.0977681000 _diffrn_orient_matrix_UB_32 0.0724043000 _diffrn_orient_matrix_UB_33 0.0808193000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_unetI/netI 0.0239 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 34588 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.988 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 71.740 _diffrn_reflns_theta_min 4.097 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.022 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.39403 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.415 _exptl_crystal_description block _exptl_crystal_F_000 824 _refine_diff_density_max 0.228 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.060 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 525 _refine_ls_number_reflns 7310 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.045 _refine_ls_R_factor_all 0.0725 _refine_ls_R_factor_gt 0.0614 _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^)+(0.0983P)^2^+0.4424P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1672 _refine_ls_wR_factor_ref 0.1799 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5870 _reflns_number_total 7310 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL exp_15640 in P-1 #2 exp_15640.res created by SHELXL-2018/3 at 10:51:04 on 27-Feb-2019 REM reset to P-1 #2 CELL 1.54184 11.12251 12.83072 13.89277 100.8646 91.7108 103.3573 ZERR 2 0.00039 0.00052 0.00046 0.0031 0.0028 0.0032 LATT 1 SFAC C H F N UNIT 88 60 20 8 L.S. 10 PLAN 5 TEMP 24.85 BOND fmap 2 acta REM REM REM WGHT 0.098300 0.442400 FVAR 6.49363 F1 3 0.292642 0.357702 0.117469 11.00000 0.05273 0.05125 = 0.10982 0.02260 0.00408 0.00731 F2 3 -0.142107 0.270513 0.136891 11.00000 0.05233 0.04856 = 0.12453 0.02574 0.00159 0.01205 N3 4 -0.013517 0.124810 0.156707 11.00000 0.05079 0.03322 = 0.06315 0.01130 0.00095 0.01253 N4 4 0.014645 0.025695 0.157105 11.00000 0.04496 0.03348 = 0.07047 0.01439 0.00302 0.01177 F5 3 0.286919 0.559823 0.109531 11.00000 0.07739 0.04978 = 0.17695 0.04294 0.00734 -0.00331 C6 1 -0.087481 -0.065044 0.148278 11.00000 0.04630 0.03566 = 0.05255 0.01376 -0.00161 0.00899 F7 3 -0.144005 0.474273 0.131192 11.00000 0.07448 0.06093 = 0.16953 0.03726 0.00367 0.03290 C8 1 0.075846 0.303405 0.129097 11.00000 0.05484 0.03470 = 0.05371 0.00859 -0.00443 0.00848 C9 1 0.210908 -0.037920 0.158365 11.00000 0.04021 0.04078 = 0.06727 0.01583 0.00089 0.00840 C10 1 -0.033344 0.338719 0.131629 11.00000 0.05570 0.03900 = 0.07153 0.01496 -0.00333 0.00978 C11 1 -0.206708 -0.051271 0.160250 11.00000 0.05043 0.04074 = 0.07126 0.01553 0.00717 0.01340 AFIX 43 H11 2 -0.219991 0.018801 0.173922 11.00000 -1.20000 AFIX 0 C12 1 0.130832 0.019751 0.109679 11.00000 0.04506 0.03809 = 0.05401 0.00938 0.00003 0.01018 AFIX 13 H12 2 0.110324 -0.017640 0.040835 11.00000 -1.20000 AFIX 0 C13 1 0.182349 0.382558 0.120905 11.00000 0.05408 0.04186 = 0.06876 0.01320 -0.00357 0.00806 C14 1 0.080637 0.190583 0.132293 11.00000 0.04811 0.03401 = 0.05230 0.00813 -0.00306 0.00886 C15 1 -0.171509 -0.259270 0.121478 11.00000 0.05728 0.03628 = 0.06929 0.01716 -0.00329 0.00977 AFIX 43 H15 2 -0.158522 -0.329467 0.108946 11.00000 -1.20000 AFIX 0 C16 1 -0.305457 -0.140759 0.152002 11.00000 0.04813 0.04959 = 0.07763 0.01921 0.00916 0.01248 AFIX 43 H16 2 -0.384578 -0.129667 0.160038 11.00000 -1.20000 AFIX 0 C17 1 -0.070508 -0.171001 0.128801 11.00000 0.04612 0.03979 = 0.07206 0.01716 -0.00205 0.01290 AFIX 43 H17 2 0.008471 -0.182427 0.120734 11.00000 -1.20000 AFIX 0 F18 3 0.069399 0.623031 0.117421 11.00000 0.10211 0.04112 = 0.19064 0.04220 -0.00054 0.01961 C19 1 0.189862 0.141379 0.113482 11.00000 0.04716 0.03858 = 0.06230 0.01421 0.00068 0.00773 AFIX 23 H19A 2 0.254793 0.170631 0.166340 11.00000 -1.20000 H19B 2 0.223433 0.153203 0.051712 11.00000 -1.20000 AFIX 0 C20 1 -0.290485 -0.247011 0.132059 11.00000 0.05086 0.04407 = 0.06323 0.01950 0.00047 0.00373 C21 1 0.181079 0.488343 0.116785 11.00000 0.06759 0.03916 = 0.09064 0.01974 -0.00345 0.00093 N22 4 -0.482027 -0.420172 0.364518 11.00000 0.08062 0.06430 = 0.06784 0.00844 0.00204 0.00817 C23 1 0.071772 0.519871 0.120869 11.00000 0.07945 0.03638 = 0.10569 0.02378 -0.00573 0.01311 C24 1 -0.711191 -0.672705 0.371660 11.00000 0.06187 0.06674 = 0.06008 0.00394 0.00457 0.01725 AFIX 43 H24 2 -0.661008 -0.721675 0.370318 11.00000 -1.20000 AFIX 0 C25 1 0.262882 -0.114541 0.100709 11.00000 0.05381 0.04639 = 0.09003 0.01200 0.00465 0.01517 AFIX 43 H25 2 0.249224 -0.127804 0.032649 11.00000 -1.20000 AFIX 0 C26 1 -0.399605 -0.344802 0.120946 11.00000 0.06130 0.05540 = 0.10023 0.02872 0.00442 -0.00002 AFIX 137 H26A 2 -0.443134 -0.356561 0.057635 11.00000 -1.50000 H26B 2 -0.454466 -0.331581 0.171433 11.00000 -1.50000 H26C 2 -0.370539 -0.408393 0.126710 11.00000 -1.50000 AFIX 0 N27 4 -0.532464 -0.529499 0.354275 11.00000 0.06239 0.05840 = 0.08633 0.00370 0.00548 0.01184 C28 1 -0.035491 0.444821 0.128367 11.00000 0.06583 0.04591 = 0.09315 0.01847 -0.00417 0.02022 C29 1 0.234158 -0.017793 0.258292 11.00000 0.06025 0.08498 = 0.07157 0.02461 -0.00110 0.02429 AFIX 43 H29 2 0.201864 0.034259 0.298142 11.00000 -1.20000 AFIX 0 C30 1 -0.445904 -0.690382 0.292022 11.00000 0.05072 0.06472 = 0.07509 0.01379 0.00649 0.01539 C31 1 -0.362876 -0.402598 0.375026 11.00000 0.07260 0.07905 = 0.05232 0.01029 -0.00228 -0.00311 C32 1 -0.837224 -0.707278 0.380831 11.00000 0.06445 0.07665 = 0.05964 0.00199 0.00471 0.00921 AFIX 43 H32 2 -0.870023 -0.779501 0.385647 11.00000 -1.20000 AFIX 0 C33 1 -0.659393 -0.564981 0.364449 11.00000 0.06079 0.06529 = 0.05379 -0.00157 -0.00082 0.01576 C34 1 -0.462955 -0.687299 0.194376 11.00000 0.06768 0.08204 = 0.07369 0.00510 -0.00306 0.02571 AFIX 43 H34 2 -0.472437 -0.623523 0.175825 11.00000 -1.20000 AFIX 0 F35 3 -0.449620 -0.204935 0.422594 11.00000 0.15548 0.07770 = 0.12916 0.02274 -0.01689 0.02026 C36 1 -0.737855 -0.494233 0.365885 11.00000 0.07635 0.06908 = 0.07210 0.00051 -0.00478 0.02515 AFIX 43 H36 2 -0.705935 -0.422050 0.360538 11.00000 -1.20000 AFIX 0 F37 3 -0.104430 -0.356904 0.351876 11.00000 0.08740 0.16160 = 0.14477 0.01263 0.02463 -0.01748 C38 1 -0.438831 -0.591001 0.370446 11.00000 0.06262 0.07535 = 0.06282 0.01228 0.00328 0.01616 AFIX 13 H38 2 -0.447296 -0.612325 0.434496 11.00000 -1.20000 AFIX 0 C39 1 0.354562 -0.152416 0.240872 11.00000 0.06180 0.10118 = 0.15127 0.07234 0.01211 0.03627 AFIX 43 H39 2 0.401589 -0.191790 0.268928 11.00000 -1.20000 AFIX 0 C40 1 0.306749 -0.075851 0.300331 11.00000 0.07424 0.13565 = 0.09115 0.05699 -0.00356 0.03060 AFIX 43 H40 2 0.322565 -0.062682 0.368203 11.00000 -1.20000 AFIX 0 C41 1 -0.317730 -0.503177 0.374152 11.00000 0.06314 0.08769 = 0.07220 0.00193 0.00011 0.00921 AFIX 23 H41A 2 -0.265103 -0.496401 0.433055 11.00000 -1.20000 H41B 2 -0.272344 -0.519338 0.316888 11.00000 -1.20000 AFIX 0 C42 1 0.333988 -0.170852 0.142706 11.00000 0.06187 0.06056 = 0.14219 0.03258 0.01420 0.02651 AFIX 43 H42 2 0.367979 -0.221863 0.103113 11.00000 -1.20000 AFIX 0 F43 3 -0.305088 -0.008056 0.432257 11.00000 0.28470 0.08344 = 0.14328 0.03454 -0.04686 -0.01297 C44 1 -0.156778 -0.273606 0.372442 11.00000 0.09861 0.12056 = 0.06795 0.02381 -0.00361 -0.03319 C45 1 -0.253235 -0.095211 0.413269 11.00000 0.20556 0.07613 = 0.07962 0.02785 -0.02881 -0.02063 C46 1 -0.915370 -0.637778 0.383025 11.00000 0.06230 0.09796 = 0.06134 -0.00370 0.00096 0.02007 C47 1 -0.862963 -0.531404 0.375248 11.00000 0.07327 0.09466 = 0.07234 -0.00676 -0.00589 0.03665 AFIX 43 H47 2 -0.913773 -0.482976 0.376354 11.00000 -1.20000 AFIX 0 C48 1 -0.431330 -0.876070 0.245831 11.00000 0.11272 0.07374 = 0.16917 0.02508 0.05669 0.03738 AFIX 43 H48 2 -0.420013 -0.939583 0.263838 11.00000 -1.20000 AFIX 0 C49 1 -0.284863 -0.291921 0.384508 11.00000 0.10509 0.08263 = 0.05313 0.01746 -0.00705 -0.01255 C50 1 -0.327970 -0.198463 0.405553 11.00000 0.12342 0.09232 = 0.07209 0.02863 -0.01620 -0.01997 F51 3 -0.058502 0.019538 0.406510 11.00000 0.26400 0.13710 = 0.11366 0.04624 -0.03670 -0.10647 C52 1 -0.128361 -0.081591 0.399912 11.00000 0.18752 0.11433 = 0.07070 0.03443 -0.02533 -0.06940 C53 1 -0.082546 -0.170837 0.381737 11.00000 0.13151 0.14851 = 0.07679 0.03238 -0.00727 -0.05959 C54 1 -1.052566 -0.677274 0.392833 11.00000 0.06316 0.14894 = 0.10299 -0.00001 0.00837 0.02186 AFIX 137 H54A 2 -1.087420 -0.737787 0.339961 11.00000 -1.50000 H54B 2 -1.092536 -0.618951 0.390294 11.00000 -1.50000 H54C 2 -1.064871 -0.700166 0.454474 11.00000 -1.50000 AFIX 0 F55 3 0.037143 -0.156867 0.369813 11.00000 0.12900 0.23726 = 0.14680 0.04317 0.01228 -0.08668 C56 1 -0.448398 -0.873420 0.151342 11.00000 0.07692 0.07792 = 0.16320 -0.02310 0.02523 0.01527 AFIX 43 H56 2 -0.448504 -0.934966 0.103647 11.00000 -1.20000 AFIX 0 C57 1 -0.430296 -0.786332 0.316556 11.00000 0.09199 0.08665 = 0.11955 0.04045 0.03080 0.03688 AFIX 43 H57 2 -0.418910 -0.789639 0.382404 11.00000 -1.20000 AFIX 0 C58 1 -0.465914 -0.780256 0.123579 11.00000 0.07300 0.12401 = 0.08573 -0.01289 -0.00102 0.02488 AFIX 43 H58 2 -0.479740 -0.779523 0.057386 11.00000 -1.20000 AFIX 0 HKLF 4 REM exp_15640 in P-1 #2 REM wR2 = 0.1799, GooF = S = 1.045, Restrained GooF = 1.045 for all data REM R1 = 0.0614 for 5870 Fo > 4sig(Fo) and 0.0725 for all 7310 data REM 525 parameters refined using 0 restraints END WGHT 0.0983 0.4424 REM Highest difference peak 0.228, deepest hole -0.313, 1-sigma level 0.060 Q1 1 -0.4166 -0.2071 0.3625 11.00000 0.05 0.23 Q2 1 0.0163 -0.1788 0.1735 11.00000 0.05 0.21 Q3 1 0.1216 0.3337 0.0858 11.00000 0.05 0.20 Q4 1 -0.4003 -0.4158 0.0534 11.00000 0.05 0.20 Q5 1 0.1266 0.3428 0.1540 11.00000 0.05 0.18 REM The information below was added by Olex2. REM REM R1 = 0.0614 for 5870 Fo > 4sig(Fo) and 0.0725 for all 34588 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.23, deepest hole -0.31 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0725 REM R1_gt = 0.0614 REM wR_ref = 0.1799 REM GOOF = 1.045 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 34588 REM Reflections_gt = 5870 REM Parameters = n/a REM Hole = -0.31 REM Peak = 0.23 REM Flack = n/a ; _cod_data_source_file c9sc03111a2.cif _cod_data_source_block exp_15640 _cod_depositor_comments ; 2022-04-26 Z value and formula fixed to values more according to usual chemical conventions. miguel ; _cod_original_formula_sum 'C44 H30 F10 N4' _cod_original_formula_weight 804.72 _cod_original_formula_moiety '2(C22 H15 F5 N2)' _cod_original_formula_units_Z 2 _cod_original_cell_volume 1888.83(12) _cod_database_code 1552226 _shelx_shelxl_version_number 2018/3 _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. ; _reflns_odcompleteness_completeness 99.93 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C12(H12), C38(H38) 2.b Secondary CH2 refined with riding coordinates: C19(H19A,H19B), C41(H41A,H41B) 2.c Aromatic/amide H refined with riding coordinates: C11(H11), C15(H15), C16(H16), C17(H17), C24(H24), C25(H25), C29(H29), C32(H32), C34(H34), C36(H36), C39(H39), C40(H40), C42(H42), C47(H47), C48(H48), C56(H56), C57(H57), C58(H58) 2.d Idealised Me refined as rotating group: C26(H26A,H26B,H26C), C54(H54A,H54B,H54C) ; _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 1.676 _oxdiff_exptl_absorpt_empirical_full_min 0.673 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn F1 F 0.29264(11) 0.35770(10) 0.11747(11) 0.0713(4) Uani 1 1 d . F2 F -0.14211(11) 0.27051(10) 0.13689(11) 0.0741(4) Uani 1 1 d . N3 N -0.01352(14) 0.12481(11) 0.15671(11) 0.0485(4) Uani 1 1 d . N4 N 0.01465(14) 0.02570(11) 0.15711(12) 0.0488(4) Uani 1 1 d . F5 F 0.28692(14) 0.55982(11) 0.10953(15) 0.1018(6) Uani 1 1 d . C6 C -0.08748(16) -0.06504(13) 0.14828(13) 0.0444(4) Uani 1 1 d . F7 F -0.14401(14) 0.47427(12) 0.13119(15) 0.0971(5) Uani 1 1 d . C8 C 0.07585(18) 0.30341(14) 0.12910(13) 0.0484(4) Uani 1 1 d . C9 C 0.21091(16) -0.03792(14) 0.15836(14) 0.0490(4) Uani 1 1 d . C10 C -0.03334(19) 0.33872(15) 0.13163(16) 0.0553(5) Uani 1 1 d . C11 C -0.20671(18) -0.05127(15) 0.16025(15) 0.0531(4) Uani 1 1 d . H11 H -0.219991 0.018801 0.173922 0.064 Uiso 1 1 calc R C12 C 0.13083(16) 0.01975(14) 0.10968(13) 0.0458(4) Uani 1 1 d . H12 H 0.110324 -0.017640 0.040835 0.055 Uiso 1 1 calc R C13 C 0.18235(19) 0.38256(16) 0.12091(15) 0.0554(5) Uani 1 1 d . C14 C 0.08064(16) 0.19058(13) 0.13229(13) 0.0452(4) Uani 1 1 d . C15 C -0.17151(18) -0.25927(15) 0.12148(15) 0.0538(5) Uani 1 1 d . H15 H -0.158522 -0.329467 0.108946 0.065 Uiso 1 1 calc R C16 C -0.30546(18) -0.14076(16) 0.15200(16) 0.0574(5) Uani 1 1 d . H16 H -0.384578 -0.129667 0.160038 0.069 Uiso 1 1 calc R C17 C -0.07051(17) -0.17100(14) 0.12880(15) 0.0516(4) Uani 1 1 d . H17 H 0.008471 -0.182427 0.120734 0.062 Uiso 1 1 calc R F18 F 0.06940(16) 0.62303(11) 0.11742(16) 0.1086(6) Uani 1 1 d . C19 C 0.18986(17) 0.14138(14) 0.11348(15) 0.0493(4) Uani 1 1 d . H19A H 0.254793 0.170631 0.166340 0.059 Uiso 1 1 calc R H19B H 0.223433 0.153203 0.051712 0.059 Uiso 1 1 calc R C20 C -0.29048(18) -0.24701(15) 0.13206(15) 0.0529(4) Uani 1 1 d . C21 C 0.1811(2) 0.48834(16) 0.11679(18) 0.0671(6) Uani 1 1 d . N22 N -0.4820(2) -0.42017(17) 0.36452(15) 0.0732(5) Uani 1 1 d . C23 C 0.0718(2) 0.51987(17) 0.1209(2) 0.0730(6) Uani 1 1 d . C24 C -0.7112(2) -0.67271(19) 0.37166(16) 0.0638(5) Uani 1 1 d . H24 H -0.661008 -0.721675 0.370318 0.077 Uiso 1 1 calc R C25 C 0.26288(19) -0.11454(17) 0.10071(19) 0.0631(5) Uani 1 1 d . H25 H 0.249224 -0.127804 0.032649 0.076 Uiso 1 1 calc R C26 C -0.3996(2) -0.34480(18) 0.1209(2) 0.0729(6) Uani 1 1 d . H26A H -0.443134 -0.356561 0.057635 0.109 Uiso 1 1 calc GR H26B H -0.454466 -0.331581 0.171433 0.109 Uiso 1 1 calc GR H26C H -0.370539 -0.408393 0.126710 0.109 Uiso 1 1 calc GR N27 N -0.53246(18) -0.52950(16) 0.35428(15) 0.0710(5) Uani 1 1 d . C28 C -0.0355(2) 0.44482(17) 0.12837(19) 0.0668(6) Uani 1 1 d . C29 C 0.2342(2) -0.0178(2) 0.25829(18) 0.0701(6) Uani 1 1 d . H29 H 0.201864 0.034259 0.298142 0.084 Uiso 1 1 calc R C30 C -0.44590(19) -0.69038(18) 0.29202(17) 0.0633(5) Uani 1 1 d . C31 C -0.3629(2) -0.4026(2) 0.37503(16) 0.0721(6) Uani 1 1 d . C32 C -0.8372(2) -0.7073(2) 0.38083(16) 0.0698(6) Uani 1 1 d . H32 H -0.870023 -0.779501 0.385647 0.084 Uiso 1 1 calc R C33 C -0.6594(2) -0.56498(19) 0.36445(15) 0.0618(5) Uani 1 1 d . C34 C -0.4630(2) -0.6873(2) 0.19438(18) 0.0748(6) Uani 1 1 d . H34 H -0.472437 -0.623523 0.175825 0.090 Uiso 1 1 calc R F35 F -0.4496(2) -0.20494(15) 0.42259(16) 0.1224(7) Uani 1 1 d . C36 C -0.7379(2) -0.4942(2) 0.36588(18) 0.0733(6) Uani 1 1 d . H36 H -0.705935 -0.422050 0.360538 0.088 Uiso 1 1 calc R F37 F -0.1044(2) -0.3569(2) 0.35188(19) 0.1413(9) Uani 1 1 d . C38 C -0.4388(2) -0.5910(2) 0.37045(17) 0.0673(6) Uani 1 1 d . H38 H -0.447296 -0.612325 0.434496 0.081 Uiso 1 1 calc R C39 C 0.3546(2) -0.1524(3) 0.2409(3) 0.0956(10) Uani 1 1 d . H39 H 0.401589 -0.191790 0.268928 0.115 Uiso 1 1 calc R C40 C 0.3067(3) -0.0759(3) 0.3003(2) 0.0951(9) Uani 1 1 d . H40 H 0.322565 -0.062682 0.368203 0.114 Uiso 1 1 calc R C41 C -0.3177(2) -0.5032(2) 0.37415(19) 0.0778(7) Uani 1 1 d . H41A H -0.265103 -0.496401 0.433055 0.093 Uiso 1 1 calc R H41B H -0.272344 -0.519338 0.316888 0.093 Uiso 1 1 calc R C42 C 0.3340(2) -0.1709(2) 0.1427(3) 0.0845(8) Uani 1 1 d . H42 H 0.367979 -0.221863 0.103113 0.101 Uiso 1 1 calc R F43 F -0.3051(4) -0.0081(2) 0.43226(19) 0.1798(13) Uani 1 1 d . C44 C -0.1568(4) -0.2736(3) 0.3724(2) 0.1052(12) Uani 1 1 d . C45 C -0.2532(6) -0.0952(3) 0.4133(3) 0.1287(16) Uani 1 1 d . C46 C -0.9154(2) -0.6378(2) 0.38302(17) 0.0765(7) Uani 1 1 d . C47 C -0.8630(3) -0.5314(2) 0.37525(18) 0.0808(7) Uani 1 1 d . H47 H -0.913773 -0.482976 0.376354 0.097 Uiso 1 1 calc R C48 C -0.4313(3) -0.8761(3) 0.2458(4) 0.1150(12) Uani 1 1 d . H48 H -0.420013 -0.939583 0.263838 0.138 Uiso 1 1 calc R C49 C -0.2849(3) -0.2919(3) 0.38451(18) 0.0859(8) Uani 1 1 d . C50 C -0.3280(4) -0.1985(3) 0.4056(2) 0.1025(11) Uani 1 1 d . F51 F -0.0585(3) 0.0195(2) 0.40651(18) 0.1956(16) Uani 1 1 d . C52 C -0.1284(6) -0.0816(4) 0.3999(3) 0.140(2) Uani 1 1 d . C53 C -0.0825(4) -0.1708(5) 0.3817(3) 0.1335(18) Uani 1 1 d . C54 C -1.0526(3) -0.6773(3) 0.3928(3) 0.1090(11) Uani 1 1 d . H54A H -1.087420 -0.737787 0.339961 0.164 Uiso 1 1 calc GR H54B H -1.092536 -0.618951 0.390294 0.164 Uiso 1 1 calc GR H54C H -1.064871 -0.700166 0.454474 0.164 Uiso 1 1 calc GR F55 F 0.0371(2) -0.1569(3) 0.3698(2) 0.1922(15) Uani 1 1 d . C56 C -0.4484(3) -0.8734(3) 0.1513(4) 0.1126(13) Uani 1 1 d . H56 H -0.448504 -0.934966 0.103647 0.135 Uiso 1 1 calc R C57 C -0.4303(3) -0.7863(3) 0.3166(3) 0.0937(9) Uani 1 1 d . H57 H -0.418910 -0.789639 0.382404 0.112 Uiso 1 1 calc R C58 C -0.4659(3) -0.7803(3) 0.1236(2) 0.0988(10) Uani 1 1 d . H58 H -0.479740 -0.779523 0.057386 0.119 Uiso 1 1 calc R 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 0.0527(7) 0.0512(7) 0.1098(10) 0.0226(6) 0.0041(6) 0.0073(5) F2 0.0523(7) 0.0486(7) 0.1245(11) 0.0257(7) 0.0016(7) 0.0121(5) N3 0.0508(8) 0.0332(7) 0.0632(9) 0.0113(6) 0.0010(7) 0.0125(6) N4 0.0450(8) 0.0335(7) 0.0705(10) 0.0144(7) 0.0030(7) 0.0118(6) F5 0.0774(10) 0.0498(8) 0.1770(17) 0.0429(9) 0.0073(10) -0.0033(7) C6 0.0463(9) 0.0357(8) 0.0526(9) 0.0138(7) -0.0016(7) 0.0090(7) F7 0.0745(9) 0.0609(8) 0.1695(16) 0.0373(9) 0.0037(9) 0.0329(7) C8 0.0548(10) 0.0347(9) 0.0537(10) 0.0086(7) -0.0044(8) 0.0085(8) C9 0.0402(9) 0.0408(9) 0.0673(11) 0.0158(8) 0.0009(8) 0.0084(7) C10 0.0557(11) 0.0390(9) 0.0715(12) 0.0150(9) -0.0033(9) 0.0098(8) C11 0.0504(10) 0.0407(9) 0.0713(12) 0.0155(8) 0.0072(9) 0.0134(8) C12 0.0451(9) 0.0381(9) 0.0540(10) 0.0094(7) 0.0000(7) 0.0102(7) C13 0.0541(11) 0.0419(10) 0.0688(12) 0.0132(9) -0.0036(9) 0.0081(8) C14 0.0481(9) 0.0340(8) 0.0523(9) 0.0081(7) -0.0031(7) 0.0089(7) C15 0.0573(11) 0.0363(9) 0.0693(12) 0.0172(8) -0.0033(9) 0.0098(8) C16 0.0481(10) 0.0496(11) 0.0776(13) 0.0192(9) 0.0092(9) 0.0125(8) C17 0.0461(10) 0.0398(9) 0.0721(12) 0.0172(8) -0.0020(8) 0.0129(7) F18 0.1021(12) 0.0411(7) 0.1906(18) 0.0422(9) -0.0005(11) 0.0196(7) C19 0.0472(10) 0.0386(9) 0.0623(11) 0.0142(8) 0.0007(8) 0.0077(7) C20 0.0509(10) 0.0441(10) 0.0632(11) 0.0195(8) 0.0005(8) 0.0037(8) C21 0.0676(13) 0.0392(10) 0.0906(16) 0.0197(10) -0.0035(11) 0.0009(9) N22 0.0806(14) 0.0643(12) 0.0678(11) 0.0084(9) 0.0020(9) 0.0082(10) C23 0.0794(15) 0.0364(10) 0.1057(18) 0.0238(11) -0.0057(13) 0.0131(10) C24 0.0619(12) 0.0667(13) 0.0601(12) 0.0039(10) 0.0046(9) 0.0172(10) C25 0.0538(11) 0.0464(10) 0.0900(15) 0.0120(10) 0.0046(10) 0.0152(9) C26 0.0613(13) 0.0554(13) 0.1002(17) 0.0287(12) 0.0044(12) 0.0000(10) N27 0.0624(11) 0.0584(11) 0.0863(13) 0.0037(9) 0.0055(9) 0.0118(9) C28 0.0658(13) 0.0459(11) 0.0931(16) 0.0185(10) -0.0042(11) 0.0202(10) C29 0.0603(13) 0.0850(16) 0.0716(14) 0.0246(12) -0.0011(10) 0.0243(11) C30 0.0507(11) 0.0647(13) 0.0751(13) 0.0138(10) 0.0065(10) 0.0154(9) C31 0.0726(15) 0.0790(16) 0.0523(11) 0.0103(11) -0.0023(10) -0.0031(12) C32 0.0644(13) 0.0766(15) 0.0596(12) 0.0020(11) 0.0047(10) 0.0092(11) C33 0.0608(12) 0.0653(13) 0.0538(11) -0.0016(9) -0.0008(9) 0.0158(10) C34 0.0677(14) 0.0820(16) 0.0737(14) 0.0051(12) -0.0031(11) 0.0257(12) F35 0.155(2) 0.0777(11) 0.1292(16) 0.0227(10) -0.0169(14) 0.0203(12) C36 0.0763(15) 0.0691(14) 0.0721(14) 0.0005(11) -0.0048(11) 0.0251(12) F37 0.0874(13) 0.162(2) 0.1448(19) 0.0126(16) 0.0246(12) -0.0175(14) C38 0.0626(13) 0.0754(15) 0.0628(12) 0.0123(11) 0.0033(10) 0.0162(11) C39 0.0618(15) 0.101(2) 0.151(3) 0.072(2) 0.0121(16) 0.0363(14) C40 0.0742(17) 0.136(3) 0.0911(19) 0.0570(19) -0.0036(14) 0.0306(17) C41 0.0631(14) 0.0877(18) 0.0722(14) 0.0019(13) 0.0001(11) 0.0092(12) C42 0.0619(14) 0.0606(14) 0.142(3) 0.0326(16) 0.0142(15) 0.0265(11) F43 0.285(4) 0.0834(15) 0.143(2) 0.0345(14) -0.047(2) -0.0130(19) C44 0.099(2) 0.121(3) 0.0680(16) 0.0238(17) -0.0036(15) -0.033(2) C45 0.206(5) 0.076(2) 0.080(2) 0.0278(17) -0.029(2) -0.021(3) C46 0.0623(14) 0.098(2) 0.0613(13) -0.0037(12) 0.0010(10) 0.0201(13) C47 0.0733(15) 0.095(2) 0.0723(15) -0.0068(13) -0.0059(12) 0.0367(14) C48 0.113(3) 0.074(2) 0.169(4) 0.025(2) 0.057(3) 0.0374(18) C49 0.105(2) 0.0826(19) 0.0531(13) 0.0175(12) -0.0070(12) -0.0126(16) C50 0.123(3) 0.092(2) 0.0721(17) 0.0286(16) -0.0162(17) -0.020(2) F51 0.264(3) 0.137(2) 0.1137(16) 0.0462(14) -0.0367(18) -0.106(2) C52 0.188(5) 0.114(3) 0.0707(19) 0.034(2) -0.025(2) -0.069(4) C53 0.132(3) 0.149(4) 0.077(2) 0.032(2) -0.0073(19) -0.060(3) C54 0.0632(16) 0.149(3) 0.103(2) 0.000(2) 0.0084(15) 0.0219(18) F55 0.129(2) 0.237(3) 0.147(2) 0.043(2) 0.0123(15) -0.087(2) C56 0.0769(19) 0.078(2) 0.163(4) -0.023(2) 0.025(2) 0.0153(15) C57 0.0920(19) 0.0867(19) 0.120(2) 0.0404(17) 0.0308(17) 0.0369(16) C58 0.0730(17) 0.124(3) 0.0857(18) -0.0129(18) -0.0010(14) 0.0249(17) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C14 N3 N4 109.13(14) N3 N4 C6 115.85(14) N3 N4 C12 111.01(13) C6 N4 C12 122.97(14) C11 C6 N4 121.11(15) C11 C6 C17 118.40(16) C17 C6 N4 120.49(16) C10 C8 C13 115.16(16) C10 C8 C14 123.36(17) C13 C8 C14 121.46(17) C25 C9 C12 119.37(18) C29 C9 C12 121.95(18) C29 C9 C25 118.67(19) F2 C10 C8 121.22(16) F2 C10 C28 116.50(18) C28 C10 C8 122.29(19) C16 C11 C6 120.41(17) N4 C12 C9 114.12(14) N4 C12 C19 101.31(13) C9 C12 C19 114.28(15) F1 C13 C8 120.37(17) F1 C13 C21 116.62(18) C21 C13 C8 123.0(2) N3 C14 C8 119.97(16) N3 C14 C19 113.43(14) C8 C14 C19 126.55(16) C20 C15 C17 122.46(17) C11 C16 C20 122.02(18) C15 C17 C6 119.83(17) C14 C19 C12 101.43(14) C15 C20 C16 116.86(17) C15 C20 C26 121.43(18) C16 C20 C26 121.70(19) F5 C21 C13 119.6(2) F5 C21 C23 120.52(19) C23 C21 C13 119.8(2) C31 N22 N27 108.9(2) F18 C23 C21 120.4(2) F18 C23 C28 120.3(2) C21 C23 C28 119.30(18) C32 C24 C33 120.3(2) C42 C25 C9 121.0(2) N22 N27 C33 118.66(19) N22 N27 C38 112.50(19) C33 N27 C38 124.8(2) F7 C28 C10 119.6(2) F7 C28 C23 119.98(18) C23 C28 C10 120.4(2) C9 C29 C40 119.8(2) C34 C30 C38 121.0(2) C34 C30 C57 118.5(2) C57 C30 C38 120.4(2) N22 C31 C41 113.8(2) N22 C31 C49 120.4(3) C49 C31 C41 125.7(2) C46 C32 C24 122.0(2) C24 C33 N27 120.8(2) C24 C33 C36 118.1(2) C36 C33 N27 121.1(2) C30 C34 C58 119.4(3) C47 C36 C33 120.0(3) N27 C38 C30 113.90(19) N27 C38 C41 101.39(19) C30 C38 C41 112.86(19) C42 C39 C40 120.6(2) C39 C40 C29 119.8(3) C31 C41 C38 102.5(2) C39 C42 C25 120.1(3) F37 C44 C49 120.3(3) F37 C44 C53 117.7(4) C53 C44 C49 122.0(5) F43 C45 C50 118.7(5) F43 C45 C52 121.2(4) C50 C45 C52 120.0(5) C32 C46 C47 117.1(2) C32 C46 C54 121.1(3) C47 C46 C54 121.8(3) C46 C47 C36 122.4(2) C56 C48 C57 120.5(3) C44 C49 C31 121.3(3) C50 C49 C31 124.1(3) C50 C49 C44 114.6(3) F35 C50 C45 116.5(4) F35 C50 C49 120.3(3) C45 C50 C49 123.2(4) F51 C52 C45 118.6(6) F51 C52 C53 122.9(6) C53 C52 C45 118.4(4) C52 C53 C44 121.7(5) F55 C53 C44 120.3(6) F55 C53 C52 117.9(5) C48 C56 C58 120.4(3) C48 C57 C30 121.1(3) C56 C58 C34 120.0(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F1 C13 1.337(2) F2 C10 1.332(2) N3 N4 1.3791(19) N3 C14 1.282(2) N4 C6 1.410(2) N4 C12 1.479(2) F5 C21 1.334(3) C6 C11 1.388(2) C6 C17 1.393(2) F7 C28 1.345(3) C8 C10 1.390(3) C8 C13 1.394(3) C8 C14 1.470(2) C9 C12 1.502(2) C9 C25 1.391(3) C9 C29 1.369(3) C10 C28 1.376(3) C11 C16 1.378(3) C12 C19 1.537(2) C13 C21 1.373(3) C14 C19 1.501(2) C15 C17 1.385(3) C15 C20 1.377(3) C16 C20 1.389(3) F18 C23 1.340(2) C20 C26 1.511(3) C21 C23 1.367(3) N22 N27 1.363(3) N22 C31 1.291(3) C23 C28 1.370(3) C24 C32 1.387(3) C24 C33 1.393(3) C25 C42 1.372(3) N27 C33 1.400(3) N27 C38 1.480(3) C29 C40 1.401(3) C30 C34 1.373(3) C30 C38 1.498(3) C30 C57 1.384(3) C31 C41 1.487(4) C31 C49 1.463(4) C32 C46 1.379(4) C33 C36 1.395(3) C34 C58 1.389(4) F35 C50 1.367(4) C36 C47 1.381(4) F37 C44 1.321(5) C38 C41 1.536(3) C39 C40 1.375(5) C39 C42 1.343(4) F43 C45 1.360(6) C44 C49 1.410(5) C44 C53 1.365(5) C45 C50 1.375(5) C45 C52 1.382(7) C46 C47 1.381(4) C46 C54 1.512(4) C48 C56 1.329(5) C48 C57 1.363(5) C49 C50 1.377(5) F51 C52 1.334(4) C52 C53 1.343(7) C53 F55 1.321(5) C56 C58 1.376(5)