#------------------------------------------------------------------------------ #$Date: 2018-09-10 11:47:35 +0300 (Mon, 10 Sep 2018) $ #$Revision: 210730 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/85/1548530.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_1548530 loop_ _publ_author_name 'Shit, Shyamapada' 'Nandy, Madhusudan' 'Rizzoli, Corrado' 'Desplanches, C\'edric' 'Mitra, Samiran' _publ_section_title ; Crystal structure, characterization and magnetic properties of a 1D copper(II) polymer incorporating a Schiff base with carboxylate side arm ; _journal_issue 6 _journal_name_full 'Journal of Chemical Sciences' _journal_page_first 913 _journal_page_last 920 _journal_paper_doi 10.1007/s12039-016-1082-4 _journal_volume 128 _journal_year 2016 _chemical_formula_moiety 'C25 H12 F6 N2 O6' _chemical_formula_sum 'C25 H12 F6 N2 O6' _chemical_formula_weight 550.37 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _cell_angle_alpha 90 _cell_angle_beta 96.341(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.802(3) _cell_length_b 7.0481(16) _cell_length_c 19.530(4) _cell_measurement_reflns_used 9886 _cell_measurement_temperature 105(2) _cell_measurement_theta_max 30.42 _cell_measurement_theta_min 2.59 _cell_volume 2161.8(8) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 2012)' _computing_publication_material 'publCIF (Westrip, 2010)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXTL Intrinsic Phasing (Sheldrick, 2014)' _diffrn_ambient_temperature 105(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type ; Bruker Kappa D8 Quest CMOS diffractometer (with an Oxford Cryosystems cryostream cooler) ; _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0757 _diffrn_reflns_av_unetI/netI 0.0685 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 10886 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.580 _diffrn_reflns_theta_min 2.594 _diffrn_source 'I\mS microfocus tube' _exptl_absorpt_coefficient_mu 0.155 _exptl_absorpt_correction_T_max 0.746070 _exptl_absorpt_correction_T_min 0.570009 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'TWINABS (Sheldrick, 2002)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.691 _exptl_crystal_description fragment _exptl_crystal_F_000 1112 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF' _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.040 _refine_diff_density_max 0.479 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.088 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 353 _refine_ls_number_reflns 10886 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.025 _refine_ls_R_factor_all 0.0913 _refine_ls_R_factor_gt 0.0599 _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^)+(0.0517P)^2^+1.4080P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1198 _refine_ls_wR_factor_ref 0.1333 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 8064 _reflns_number_total 10886 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file J-Chem-Sci-2016-128-913.cif _cod_data_source_block revised_scd0398_twin4 _cod_original_cell_volume 2161.7(8) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 1548530 #BEGIN Tags that were not found in dictionaries: _shelx_estimated_absorpt_t_min 0.941 _shelx_estimated_absorpt_t_max 0.994 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL scd0398_twin4 in P2(1)/n CELL 0.71073 15.80159 7.04807 19.52970 90.0000 96.3410 90.0000 ZERR 4.000 0.00317 0.00160 0.00429 0.0000 0.0095 0.0000 rem rem Component Vol rem 1.0(0) 2161.73 rem 1.27 rem rem Rotated from first domain by 180.0 degrees about rem reciprocal axis -0.999 0.000 1.000 and real axis 1.000 0.000 -0.619 rem rem Twin law to convert hkl from first to 0.235 0.000 -0.765 rem this domain (SHELXL TWIN matrix): 0.000 -1.000 0.000 rem -1.236 0.000 -0.235 rem LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H N O F UNIT 100 48 8 24 24 ACTA CONF BOND $H FMAP 2 SIZE 0.04 0.3 0.4 TEMP -168 L.S. 20 PLAN 20 WGHT 0.051700 1.408000 BASF 0.42925 FVAR 0.48134 F1 5 0.233812 0.204758 0.513778 11.00000 0.04231 0.01037 = 0.04473 0.00182 0.02146 -0.00153 F2 5 0.303782 0.396056 0.585064 11.00000 0.02641 0.04180 = 0.01578 0.01100 0.00111 0.00597 F3 5 0.102657 0.405889 0.513943 11.00000 0.01899 0.02177 = 0.04032 0.00505 0.00120 -0.01162 F4 5 0.171142 0.593079 0.587397 11.00000 0.03690 0.02421 = 0.01853 -0.00445 0.00991 0.00303 F5 5 0.110590 0.641807 0.419446 11.00000 0.01288 0.03653 = 0.02483 0.00676 -0.00200 0.00098 F6 5 0.171406 0.839393 0.493757 11.00000 0.03092 0.01204 = 0.03670 -0.00122 0.01563 0.00114 O1 4 0.587561 0.230764 0.197229 11.00000 0.02054 0.02188 = 0.02337 0.00344 0.00485 0.00754 O2 4 0.374471 0.666483 0.153487 11.00000 0.02492 0.03029 = 0.01879 0.00077 0.00004 0.01263 O3 4 0.369727 0.377268 0.454778 11.00000 0.01802 0.02447 = 0.01392 0.00552 0.00477 0.00915 O4 4 0.275344 0.746176 0.389121 11.00000 0.01040 0.02195 = 0.01969 0.01050 0.00224 0.00037 O5 4 0.603671 0.748247 0.237620 11.00000 0.01894 0.02106 = 0.02229 -0.00875 0.00522 -0.00569 O6 4 0.648116 1.164017 0.417630 11.00000 0.01882 0.01738 = 0.01515 -0.00361 0.00119 -0.00244 N1 3 0.469966 0.428582 0.191779 11.00000 0.01357 0.01562 = 0.01165 -0.00100 0.00036 0.00170 N2 3 0.600959 0.947373 0.332338 11.00000 0.01033 0.01216 = 0.01405 -0.00175 0.00247 -0.00246 C1 1 0.543112 0.352635 0.168358 11.00000 0.01367 0.01540 = 0.01649 -0.00516 0.00148 -0.00133 C2 1 0.553434 0.450366 0.102367 11.00000 0.01891 0.02031 = 0.01307 -0.00338 0.00195 -0.00295 AFIX 43 H2 2 0.597040 0.425680 0.073749 11.00000 -1.20000 AFIX 0 C3 1 0.492061 0.577215 0.089985 11.00000 0.02403 0.01999 = 0.01214 -0.00002 0.00028 -0.00006 AFIX 43 H3 2 0.484736 0.659300 0.051200 11.00000 -1.20000 AFIX 0 C4 1 0.436174 0.570832 0.146640 11.00000 0.01875 0.01856 = 0.01172 -0.00285 -0.00263 0.00160 C5 1 0.444222 0.397520 0.258530 11.00000 0.01602 0.01134 = 0.01440 -0.00054 0.00280 0.00118 C6 1 0.359636 0.359587 0.265560 11.00000 0.01413 0.01868 = 0.01715 -0.00230 -0.00094 -0.00249 AFIX 43 H6 2 0.320037 0.341099 0.225859 11.00000 -1.20000 AFIX 0 C7 1 0.332795 0.348621 0.331006 11.00000 0.01439 0.01726 = 0.01995 -0.00119 0.00380 -0.00065 AFIX 43 H7 2 0.275055 0.322614 0.336900 11.00000 -1.20000 AFIX 0 C8 1 0.392633 0.376685 0.386936 11.00000 0.01842 0.01537 = 0.01215 0.00317 0.00542 0.00376 C9 1 0.477736 0.403043 0.381050 11.00000 0.01591 0.01425 = 0.01377 0.00098 -0.00181 0.00493 AFIX 43 H9 2 0.517752 0.413027 0.420926 11.00000 -1.20000 AFIX 0 C10 1 0.503900 0.414723 0.315938 11.00000 0.01171 0.01131 = 0.01734 -0.00081 0.00140 0.00217 AFIX 43 H10 2 0.562264 0.434368 0.310516 11.00000 -1.20000 AFIX 0 C11 1 0.297835 0.469073 0.466775 11.00000 0.01425 0.01405 = 0.01140 0.00043 0.00349 0.00007 C12 1 0.253632 0.389464 0.523752 11.00000 0.02205 0.01212 = 0.01525 0.00310 0.00404 -0.00188 C13 1 0.173405 0.511774 0.525824 11.00000 0.01549 0.01469 = 0.01581 -0.00266 0.00540 -0.00667 C14 1 0.177586 0.661882 0.468893 11.00000 0.01326 0.01287 = 0.01850 -0.00011 0.00310 -0.00022 C15 1 0.259547 0.626894 0.440240 11.00000 0.01249 0.01309 = 0.01238 0.00221 0.00259 -0.00226 C16 1 0.358665 0.799830 0.378864 11.00000 0.01056 0.01162 = 0.01897 0.00347 0.00506 0.00199 C17 1 0.422581 0.821959 0.432564 11.00000 0.01543 0.01317 = 0.01333 0.00137 0.00403 -0.00004 AFIX 43 H17 2 0.411557 0.802823 0.478906 11.00000 -1.20000 AFIX 0 C18 1 0.503206 0.872755 0.417251 11.00000 0.01413 0.01274 = 0.01264 -0.00042 -0.00017 -0.00169 AFIX 43 H18 2 0.548596 0.884662 0.453173 11.00000 -1.20000 AFIX 0 C19 1 0.517538 0.906144 0.349515 11.00000 0.01113 0.00910 = 0.01590 -0.00003 0.00322 0.00017 C20 1 0.451646 0.893676 0.296737 11.00000 0.01435 0.01359 = 0.01214 0.00277 0.00239 -0.00006 AFIX 43 H20 2 0.461121 0.923992 0.250803 11.00000 -1.20000 AFIX 0 C21 1 0.371660 0.836497 0.311565 11.00000 0.01140 0.01596 = 0.01606 0.00333 0.00010 0.00191 AFIX 43 H21 2 0.326343 0.822786 0.275677 11.00000 -1.20000 AFIX 0 C22 1 0.637089 0.865070 0.276853 11.00000 0.01311 0.01524 = 0.01583 -0.00189 0.00439 0.00019 C23 1 0.724338 0.946370 0.278336 11.00000 0.01275 0.01831 = 0.02178 -0.00157 0.00482 -0.00118 AFIX 43 H23 2 0.763949 0.918699 0.246494 11.00000 -1.20000 AFIX 0 C24 1 0.737425 1.063411 0.331345 11.00000 0.01117 0.01483 = 0.02011 0.00199 0.00132 -0.00215 AFIX 43 H24 2 0.788479 1.132021 0.344129 11.00000 -1.20000 AFIX 0 C25 1 0.659795 1.070847 0.367791 11.00000 0.01308 0.01102 = 0.01382 0.00352 -0.00163 -0.00025 HKLF 5 REM scd0398_twin4 in P2(1)/n REM R1 = 0.0599 for 8064 Fo > 4sig(Fo) and 0.0913 for all 10886 data REM 353 parameters refined using 0 restraints END WGHT 0.0517 1.4080 REM Highest difference peak 0.479, deepest hole -0.343, 1-sigma level 0.088 Q1 1 0.4187 0.8328 0.2971 11.00000 0.05 0.48 Q2 1 0.2209 0.6602 0.4532 11.00000 0.05 0.45 Q3 1 0.2736 0.4310 0.4986 11.00000 0.05 0.42 Q4 1 0.2767 0.5228 0.4344 11.00000 0.05 0.42 Q5 1 0.6991 1.0800 0.3508 11.00000 0.05 0.40 Q6 1 0.6838 0.8912 0.2739 11.00000 0.05 0.39 Q7 1 0.1674 0.5776 0.4906 11.00000 0.05 0.38 Q8 1 0.4524 0.8911 0.4261 11.00000 0.05 0.36 Q9 1 0.2617 0.5687 0.4716 11.00000 0.05 0.36 Q10 1 0.2189 0.4593 0.5299 11.00000 0.05 0.36 Q11 1 0.4884 0.4629 0.3475 11.00000 0.05 0.35 Q12 1 0.3774 0.3847 0.4129 11.00000 0.05 0.35 Q13 1 0.2619 0.6681 0.4163 11.00000 0.05 0.35 Q14 1 0.5034 0.9327 0.3814 11.00000 0.05 0.35 Q15 1 0.4564 0.5578 0.1102 11.00000 0.05 0.34 Q16 1 0.6124 0.8761 0.3148 11.00000 0.05 0.34 Q17 1 0.6221 1.1004 0.4373 11.00000 0.05 0.34 Q18 1 0.4027 0.8906 0.3047 11.00000 0.05 0.34 Q19 1 0.4771 0.5822 0.0673 11.00000 0.05 0.34 Q20 1 0.5002 0.3973 0.3478 11.00000 0.05 0.33 ; _shelx_res_checksum 94641 #END Tags that were not found in dictionaries 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 F1 F 0.23381(10) 0.2048(2) 0.51378(8) 0.0312(4) Uani 1 1 d . . . . . F2 F 0.30378(9) 0.3961(2) 0.58506(7) 0.0281(4) Uani 1 1 d . . . . . F3 F 0.10266(9) 0.4059(2) 0.51394(8) 0.0272(4) Uani 1 1 d . . . . . F4 F 0.17114(10) 0.5931(2) 0.58740(7) 0.0260(3) Uani 1 1 d . . . . . F5 F 0.11059(8) 0.6418(2) 0.41945(7) 0.0251(3) Uani 1 1 d . . . . . F6 F 0.17141(9) 0.83939(19) 0.49376(8) 0.0257(3) Uani 1 1 d . . . . . O1 O 0.58756(10) 0.2308(2) 0.19723(8) 0.0217(4) Uani 1 1 d . . . . . O2 O 0.37447(11) 0.6665(3) 0.15349(9) 0.0248(4) Uani 1 1 d . . . . . O3 O 0.36973(10) 0.3773(2) 0.45478(8) 0.0186(4) Uani 1 1 d . . . . . O4 O 0.27534(9) 0.7462(2) 0.38912(8) 0.0173(3) Uani 1 1 d . . . . . O5 O 0.60367(10) 0.7482(2) 0.23762(8) 0.0205(4) Uani 1 1 d . . . . . O6 O 0.64812(10) 1.1640(2) 0.41763(8) 0.0172(3) Uani 1 1 d . . . . . N1 N 0.46997(11) 0.4286(3) 0.19178(9) 0.0137(4) Uani 1 1 d . . . . . N2 N 0.60096(11) 0.9474(3) 0.33234(9) 0.0121(4) Uani 1 1 d . . . . . C1 C 0.54311(14) 0.3526(3) 0.16836(12) 0.0152(4) Uani 1 1 d . . . . . C2 C 0.55343(15) 0.4504(3) 0.10237(11) 0.0174(5) Uani 1 1 d . . . . . H2 H 0.5970 0.4257 0.0737 0.021 Uiso 1 1 calc R U . . . C3 C 0.49206(15) 0.5772(3) 0.08999(12) 0.0188(5) Uani 1 1 d . . . . . H3 H 0.4847 0.6593 0.0512 0.023 Uiso 1 1 calc R U . . . C4 C 0.43617(15) 0.5708(3) 0.14664(11) 0.0167(5) Uani 1 1 d . . . . . C5 C 0.44422(14) 0.3975(3) 0.25853(11) 0.0138(4) Uani 1 1 d . . . . . C6 C 0.35964(14) 0.3596(3) 0.26556(12) 0.0168(5) Uani 1 1 d . . . . . H6 H 0.3200 0.3411 0.2259 0.020 Uiso 1 1 calc R U . . . C7 C 0.33280(15) 0.3486(3) 0.33101(12) 0.0171(5) Uani 1 1 d . . . . . H7 H 0.2751 0.3226 0.3369 0.020 Uiso 1 1 calc R U . . . C8 C 0.39263(14) 0.3767(3) 0.38694(11) 0.0150(4) Uani 1 1 d . . . . . C9 C 0.47774(14) 0.4030(3) 0.38105(11) 0.0149(4) Uani 1 1 d . . . . . H9 H 0.5178 0.4130 0.4209 0.018 Uiso 1 1 calc R U . . . C10 C 0.50390(14) 0.4147(3) 0.31594(11) 0.0135(4) Uani 1 1 d . . . . . H10 H 0.5623 0.4344 0.3105 0.016 Uiso 1 1 calc R U . . . C11 C 0.29784(14) 0.4691(3) 0.46678(11) 0.0131(4) Uani 1 1 d . . . . . C12 C 0.25363(15) 0.3895(3) 0.52375(12) 0.0163(5) Uani 1 1 d . . . . . C13 C 0.17341(14) 0.5118(3) 0.52582(11) 0.0151(4) Uani 1 1 d . . . . . C14 C 0.17759(14) 0.6619(3) 0.46889(12) 0.0148(4) Uani 1 1 d . . . . . C15 C 0.25955(14) 0.6269(3) 0.44024(11) 0.0126(4) Uani 1 1 d . . . . . C16 C 0.35867(13) 0.7998(3) 0.37886(11) 0.0135(4) Uani 1 1 d . . . . . C17 C 0.42258(14) 0.8220(3) 0.43256(11) 0.0138(4) Uani 1 1 d . . . . . H17 H 0.4116 0.8028 0.4789 0.017 Uiso 1 1 calc R U . . . C18 C 0.50321(14) 0.8728(3) 0.41725(11) 0.0133(4) Uani 1 1 d . . . . . H18 H 0.5486 0.8847 0.4532 0.016 Uiso 1 1 calc R U . . . C19 C 0.51754(13) 0.9061(3) 0.34952(11) 0.0119(4) Uani 1 1 d . . . . . C20 C 0.45165(14) 0.8937(3) 0.29674(11) 0.0133(4) Uani 1 1 d . . . . . H20 H 0.4611 0.9240 0.2508 0.016 Uiso 1 1 calc R U . . . C21 C 0.37166(14) 0.8365(3) 0.31157(12) 0.0146(4) Uani 1 1 d . . . . . H21 H 0.3263 0.8228 0.2757 0.017 Uiso 1 1 calc R U . . . C22 C 0.63709(14) 0.8651(3) 0.27685(11) 0.0145(4) Uani 1 1 d . . . . . C23 C 0.72434(14) 0.9464(3) 0.27834(12) 0.0174(5) Uani 1 1 d . . . . . H23 H 0.7639 0.9187 0.2465 0.021 Uiso 1 1 calc R U . . . C24 C 0.73743(14) 1.0634(3) 0.33134(12) 0.0154(4) Uani 1 1 d . . . . . H24 H 0.7885 1.1320 0.3441 0.018 Uiso 1 1 calc R U . . . C25 C 0.65980(13) 1.0708(3) 0.36779(11) 0.0129(4) Uani 1 1 d . . . . . 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 0.0423(9) 0.0104(7) 0.0447(9) 0.0018(7) 0.0215(7) -0.0015(6) F2 0.0264(8) 0.0418(10) 0.0158(7) 0.0110(7) 0.0011(6) 0.0060(7) F3 0.0190(7) 0.0218(8) 0.0403(9) 0.0050(7) 0.0012(6) -0.0116(6) F4 0.0369(9) 0.0242(8) 0.0185(7) -0.0044(6) 0.0099(6) 0.0030(7) F5 0.0129(7) 0.0365(9) 0.0248(8) 0.0068(6) -0.0020(6) 0.0010(6) F6 0.0309(8) 0.0120(7) 0.0367(9) -0.0012(6) 0.0156(7) 0.0011(6) O1 0.0205(9) 0.0219(9) 0.0234(9) 0.0034(7) 0.0049(7) 0.0075(7) O2 0.0249(9) 0.0303(10) 0.0188(9) 0.0008(7) 0.0000(7) 0.0126(8) O3 0.0180(8) 0.0245(9) 0.0139(8) 0.0055(7) 0.0048(6) 0.0092(7) O4 0.0104(7) 0.0219(9) 0.0197(8) 0.0105(7) 0.0022(6) 0.0004(6) O5 0.0189(8) 0.0211(9) 0.0223(8) -0.0088(7) 0.0052(6) -0.0057(7) O6 0.0188(8) 0.0174(8) 0.0152(8) -0.0036(7) 0.0012(6) -0.0024(6) N1 0.0136(9) 0.0156(9) 0.0116(9) -0.0010(7) 0.0004(7) 0.0017(7) N2 0.0103(8) 0.0122(9) 0.0140(9) -0.0017(7) 0.0025(7) -0.0025(7) C1 0.0137(10) 0.0154(11) 0.0165(11) -0.0052(9) 0.0015(8) -0.0013(9) C2 0.0189(11) 0.0203(12) 0.0131(11) -0.0034(9) 0.0019(9) -0.0030(9) C3 0.0240(12) 0.0200(12) 0.0121(11) 0.0000(9) 0.0003(9) -0.0001(10) C4 0.0188(11) 0.0186(11) 0.0117(10) -0.0028(9) -0.0026(8) 0.0016(9) C5 0.0160(11) 0.0113(10) 0.0144(11) -0.0005(8) 0.0028(8) 0.0012(8) C6 0.0141(11) 0.0187(11) 0.0171(11) -0.0023(9) -0.0009(9) -0.0025(9) C7 0.0144(11) 0.0173(11) 0.0199(12) -0.0012(9) 0.0038(9) -0.0006(9) C8 0.0184(11) 0.0154(11) 0.0122(11) 0.0032(8) 0.0054(8) 0.0038(9) C9 0.0159(11) 0.0143(10) 0.0138(10) 0.0010(9) -0.0018(8) 0.0049(9) C10 0.0117(10) 0.0113(10) 0.0173(11) -0.0008(9) 0.0014(8) 0.0022(8) C11 0.0142(10) 0.0140(10) 0.0114(10) 0.0004(8) 0.0035(8) 0.0001(8) C12 0.0221(12) 0.0121(11) 0.0153(11) 0.0031(9) 0.0040(9) -0.0019(9) C13 0.0155(11) 0.0147(10) 0.0158(11) -0.0027(9) 0.0054(8) -0.0067(9) C14 0.0133(10) 0.0129(10) 0.0185(11) -0.0001(9) 0.0031(8) -0.0002(8) C15 0.0125(10) 0.0131(10) 0.0124(10) 0.0022(8) 0.0026(8) -0.0023(8) C16 0.0106(10) 0.0116(10) 0.0190(11) 0.0035(9) 0.0051(8) 0.0020(8) C17 0.0154(11) 0.0132(10) 0.0133(10) 0.0014(8) 0.0040(8) 0.0000(8) C18 0.0141(10) 0.0127(10) 0.0126(10) -0.0004(8) -0.0002(8) -0.0017(8) C19 0.0111(10) 0.0091(10) 0.0159(10) 0.0000(8) 0.0032(8) 0.0002(8) C20 0.0143(10) 0.0136(10) 0.0121(10) 0.0028(8) 0.0024(8) -0.0001(8) C21 0.0114(10) 0.0160(11) 0.0161(11) 0.0033(9) 0.0001(8) 0.0019(9) C22 0.0131(10) 0.0152(10) 0.0158(11) -0.0019(9) 0.0044(8) 0.0002(8) C23 0.0128(11) 0.0183(12) 0.0218(12) -0.0016(9) 0.0048(9) -0.0012(9) C24 0.0112(10) 0.0148(11) 0.0201(11) 0.0020(9) 0.0013(8) -0.0021(8) C25 0.0131(10) 0.0110(10) 0.0138(10) 0.0035(8) -0.0016(8) -0.0003(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 C11 O3 C8 118.18(17) . . C15 O4 C16 121.73(17) . . C1 N1 C4 109.88(18) . . C1 N1 C5 124.84(19) . . C4 N1 C5 123.92(18) . . C25 N2 C22 109.51(17) . . C25 N2 C19 126.25(18) . . C22 N2 C19 124.23(18) . . O1 C1 N1 125.4(2) . . O1 C1 C2 128.3(2) . . N1 C1 C2 106.30(19) . . C3 C2 C1 108.9(2) . . C3 C2 H2 125.6 . . C1 C2 H2 125.6 . . C2 C3 C4 109.1(2) . . C2 C3 H3 125.5 . . C4 C3 H3 125.5 . . O2 C4 N1 126.0(2) . . O2 C4 C3 128.2(2) . . N1 C4 C3 105.83(19) . . C6 C5 C10 120.9(2) . . C6 C5 N1 119.8(2) . . C10 C5 N1 119.2(2) . . C5 C6 C7 119.8(2) . . C5 C6 H6 120.1 . . C7 C6 H6 120.1 . . C8 C7 C6 117.9(2) . . C8 C7 H7 121.1 . . C6 C7 H7 121.1 . . C9 C8 C7 123.0(2) . . C9 C8 O3 115.64(19) . . C7 C8 O3 121.3(2) . . C8 C9 C10 118.7(2) . . C8 C9 H9 120.7 . . C10 C9 H9 120.7 . . C9 C10 C5 119.5(2) . . C9 C10 H10 120.3 . . C5 C10 H10 120.3 . . C15 C11 O3 133.0(2) . . C15 C11 C12 111.87(19) . . O3 C11 C12 115.00(18) . . F1 C12 F2 105.27(18) . . F1 C12 C11 112.15(19) . . F2 C12 C11 111.66(19) . . F1 C12 C13 111.48(19) . . F2 C12 C13 111.05(19) . . C11 C12 C13 105.36(18) . . F4 C13 F3 106.82(18) . . F4 C13 C12 111.61(19) . . F3 C13 C12 110.92(18) . . F4 C13 C14 111.24(18) . . F3 C13 C14 110.98(18) . . C12 C13 C14 105.35(17) . . F6 C14 F5 105.70(18) . . F6 C14 C15 112.94(18) . . F5 C14 C15 110.96(18) . . F6 C14 C13 111.48(18) . . F5 C14 C13 110.42(18) . . C15 C14 C13 105.43(18) . . C11 C15 O4 133.6(2) . . C11 C15 C14 111.48(19) . . O4 C15 C14 114.52(19) . . C21 C16 C17 122.0(2) . . C21 C16 O4 115.30(19) . . C17 C16 O4 122.67(19) . . C16 C17 C18 118.5(2) . . C16 C17 H17 120.8 . . C18 C17 H17 120.8 . . C19 C18 C17 120.0(2) . . C19 C18 H18 120.0 . . C17 C18 H18 120.0 . . C20 C19 C18 120.7(2) . . C20 C19 N2 118.46(19) . . C18 C19 N2 120.78(19) . . C19 C20 C21 119.4(2) . . C19 C20 H20 120.3 . . C21 C20 H20 120.3 . . C16 C21 C20 119.3(2) . . C16 C21 H21 120.4 . . C20 C21 H21 120.4 . . O5 C22 N2 125.8(2) . . O5 C22 C23 127.9(2) . . N2 C22 C23 106.27(18) . . C24 C23 C22 108.6(2) . . C24 C23 H23 125.7 . . C22 C23 H23 125.7 . . C23 C24 C25 109.3(2) . . C23 C24 H24 125.3 . . C25 C24 H24 125.3 . . O6 C25 N2 125.9(2) . . O6 C25 C24 127.9(2) . . N2 C25 C24 106.23(18) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 F1 C12 1.348(3) . F2 C12 1.362(3) . F3 C13 1.343(2) . F4 C13 1.336(3) . F5 C14 1.359(3) . F6 C14 1.349(3) . O1 C1 1.209(3) . O2 C4 1.205(3) . O3 C11 1.350(3) . O3 C8 1.412(3) . O4 C15 1.349(3) . O4 C16 1.405(3) . O5 C22 1.206(3) . O6 C25 1.205(3) . N1 C1 1.396(3) . N1 C4 1.401(3) . N1 C5 1.425(3) . N2 C25 1.400(3) . N2 C22 1.405(3) . N2 C19 1.426(3) . C1 C2 1.486(3) . C2 C3 1.322(3) . C2 H2 0.9500 . C3 C4 1.491(3) . C3 H3 0.9500 . C5 C6 1.385(3) . C5 C10 1.388(3) . C6 C7 1.393(3) . C6 H6 0.9500 . C7 C8 1.378(3) . C7 H7 0.9500 . C8 C9 1.375(3) . C9 C10 1.382(3) . C9 H9 0.9500 . C10 H10 0.9500 . C11 C15 1.343(3) . C11 C12 1.487(3) . C12 C13 1.537(3) . C13 C14 1.541(3) . C14 C15 1.487(3) . C16 C21 1.377(3) . C16 C17 1.382(3) . C17 C18 1.387(3) . C17 H17 0.9500 . C18 C19 1.387(3) . C18 H18 0.9500 . C19 C20 1.385(3) . C20 C21 1.387(3) . C20 H20 0.9500 . C21 H21 0.9500 . C22 C23 1.490(3) . C23 C24 1.322(3) . C23 H23 0.9500 . C24 C25 1.486(3) . C24 H24 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 C4 N1 C1 O1 178.1(2) . . . . C5 N1 C1 O1 11.0(4) . . . . C4 N1 C1 C2 -2.2(2) . . . . C5 N1 C1 C2 -169.35(19) . . . . O1 C1 C2 C3 -178.6(2) . . . . N1 C1 C2 C3 1.8(3) . . . . C1 C2 C3 C4 -0.6(3) . . . . C1 N1 C4 O2 -178.1(2) . . . . C5 N1 C4 O2 -10.8(4) . . . . C1 N1 C4 C3 1.9(2) . . . . C5 N1 C4 C3 169.13(19) . . . . C2 C3 C4 O2 179.2(2) . . . . C2 C3 C4 N1 -0.7(3) . . . . C1 N1 C5 C6 -136.6(2) . . . . C4 N1 C5 C6 58.0(3) . . . . C1 N1 C5 C10 46.4(3) . . . . C4 N1 C5 C10 -119.0(2) . . . . C10 C5 C6 C7 3.5(3) . . . . N1 C5 C6 C7 -173.4(2) . . . . C5 C6 C7 C8 0.1(3) . . . . C6 C7 C8 C9 -4.1(3) . . . . C6 C7 C8 O3 176.8(2) . . . . C11 O3 C8 C9 138.5(2) . . . . C11 O3 C8 C7 -42.4(3) . . . . C7 C8 C9 C10 4.5(3) . . . . O3 C8 C9 C10 -176.41(19) . . . . C8 C9 C10 C5 -0.7(3) . . . . C6 C5 C10 C9 -3.2(3) . . . . N1 C5 C10 C9 173.74(19) . . . . C8 O3 C11 C15 -34.6(4) . . . . C8 O3 C11 C12 149.99(19) . . . . C15 C11 C12 F1 126.9(2) . . . . O3 C11 C12 F1 -56.7(3) . . . . C15 C11 C12 F2 -115.2(2) . . . . O3 C11 C12 F2 61.2(3) . . . . C15 C11 C12 C13 5.5(3) . . . . O3 C11 C12 C13 -178.17(18) . . . . F1 C12 C13 F4 116.1(2) . . . . F2 C12 C13 F4 -1.0(3) . . . . C11 C12 C13 F4 -122.02(19) . . . . F1 C12 C13 F3 -2.9(3) . . . . F2 C12 C13 F3 -119.9(2) . . . . C11 C12 C13 F3 118.99(19) . . . . F1 C12 C13 C14 -123.05(19) . . . . F2 C12 C13 C14 119.90(19) . . . . C11 C12 C13 C14 -1.2(2) . . . . F4 C13 C14 F6 -4.7(3) . . . . F3 C13 C14 F6 114.1(2) . . . . C12 C13 C14 F6 -125.81(19) . . . . F4 C13 C14 F5 -121.89(19) . . . . F3 C13 C14 F5 -3.1(3) . . . . C12 C13 C14 F5 117.01(19) . . . . F4 C13 C14 C15 118.2(2) . . . . F3 C13 C14 C15 -123.03(19) . . . . C12 C13 C14 C15 -2.9(2) . . . . O3 C11 C15 O4 4.7(4) . . . . C12 C11 C15 O4 -179.8(2) . . . . O3 C11 C15 C14 176.8(2) . . . . C12 C11 C15 C14 -7.7(3) . . . . C16 O4 C15 C11 -39.7(4) . . . . C16 O4 C15 C14 148.4(2) . . . . F6 C14 C15 C11 128.5(2) . . . . F5 C14 C15 C11 -113.0(2) . . . . C13 C14 C15 C11 6.6(2) . . . . F6 C14 C15 O4 -57.8(3) . . . . F5 C14 C15 O4 60.7(2) . . . . C13 C14 C15 O4 -179.76(18) . . . . C15 O4 C16 C21 148.8(2) . . . . C15 O4 C16 C17 -33.7(3) . . . . C21 C16 C17 C18 -3.5(3) . . . . O4 C16 C17 C18 179.1(2) . . . . C16 C17 C18 C19 2.1(3) . . . . C17 C18 C19 C20 1.5(3) . . . . C17 C18 C19 N2 -176.2(2) . . . . C25 N2 C19 C20 138.3(2) . . . . C22 N2 C19 C20 -42.9(3) . . . . C25 N2 C19 C18 -43.9(3) . . . . C22 N2 C19 C18 134.9(2) . . . . C18 C19 C20 C21 -3.7(3) . . . . N2 C19 C20 C21 174.1(2) . . . . C17 C16 C21 C20 1.3(3) . . . . O4 C16 C21 C20 178.9(2) . . . . C19 C20 C21 C16 2.3(3) . . . . C25 N2 C22 O5 177.6(2) . . . . C19 N2 C22 O5 -1.3(3) . . . . C25 N2 C22 C23 -0.6(2) . . . . C19 N2 C22 C23 -179.50(19) . . . . O5 C22 C23 C24 -177.1(2) . . . . N2 C22 C23 C24 1.0(3) . . . . C22 C23 C24 C25 -1.0(3) . . . . C22 N2 C25 O6 179.6(2) . . . . C19 N2 C25 O6 -1.5(3) . . . . C22 N2 C25 C24 0.0(2) . . . . C19 N2 C25 C24 178.89(19) . . . . C23 C24 C25 O6 -178.9(2) . . . . C23 C24 C25 N2 0.7(2) . . . .