#------------------------------------------------------------------------------ #$Date: 2019-06-29 05:55:18 +0300 (Sat, 29 Jun 2019) $ #$Revision: 216637 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/19/1551917.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_1551917 loop_ _publ_author_name 'Aksakal, Nuray Esra' 'Tanr\?iverdi E\,cik, Esra' 'Kazan, Hasan H\"useyin' 'Yenilmez \,Cift\,ci, G\"on\"ul' 'Yuksel, Fatma' _publ_section_title ; Novel Ruthenium(II) and Iridium(III) BODIPY Dyes: Insights Into Their Application in Photodynamic Therapy in Vitro ; _journal_name_full 'Photochemical & Photobiological Sciences' _journal_paper_doi 10.1039/C9PP00201D _journal_year 2019 _chemical_formula_sum 'C33 H27 B F2 N2 O' _chemical_formula_weight 516.37 _chemical_name_common 18gtu172_ET1_bas _chemical_name_systematic bodipy _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens mixed _audit_update_record ; 2019-02-20 deposited with the CCDC. 2019-06-27 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 109.102(18) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 26.758(9) _cell_length_b 9.137(2) _cell_length_c 22.861(6) _cell_measurement_reflns_used 2553 _cell_measurement_temperature 173.(2) _cell_measurement_theta_max 23.6911 _cell_measurement_theta_min 2.6465 _cell_volume 5281(3) _computing_cell_refinement 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 173.(2) _diffrn_detector_area_resol_mean 8.3333 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator multilayer _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0854 _diffrn_reflns_av_unetI/netI 0.0985 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 15349 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.61 _diffrn_source ImuS _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.3037 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2014/2 (Bruker AXS Inc.)' _exptl_crystal_colour 'blue violet' _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 2160 _exptl_crystal_size_max 0.459 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_min 0.137 _refine_diff_density_max 0.230 _refine_diff_density_min -0.346 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 357 _refine_ls_number_reflns 4646 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.1025 _refine_ls_R_factor_gt 0.0668 _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^)+(0.0686P)^2^+3.5550P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1584 _refine_ls_wR_factor_ref 0.1824 _reflns_number_gt 3015 _reflns_number_total 4646 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9pp00201d2.cif _cod_data_source_block I _cod_original_cell_volume 5281.(3) _cod_database_code 1551917 _shelx_res_file ; TITL 18gtu172_ET1_bas_0m in C2/c CELL 0.71073 26.7577 9.1375 22.8613 90.000 109.102 90.000 ZERR 8.00 0.00880 0.00230 0.00610 0.0000 0.0182 0.0000 LATT 7 SYMM -X, Y, 1/2-Z SFAC C H B N O F UNIT 264 216 8 16 8 16 OMIT -3 50 L.S. 10 ACTA HTAB O1 F1_$1 EQIV $1 x, -y+1, z+1/2 BOND $H DFIX 0.87 0.01 O1 H1 FMAP 2 PLAN 1 CONF TEMP -100.140 WGHT 0.068600 3.555000 FVAR 0.20436 B1 3 0.367713 0.644776 0.450889 11.00000 0.02745 0.03989 = 0.02570 0.00125 -0.00074 -0.00295 N1 4 0.417648 0.618030 0.507085 11.00000 0.02619 0.04214 = 0.02288 -0.00314 0.00043 -0.00286 N2 4 0.320670 0.586118 0.467085 11.00000 0.02590 0.04804 = 0.02700 0.00461 0.00164 -0.00158 O1 5 0.381900 0.268343 0.801033 11.00000 0.06161 0.05505 = 0.03067 0.00843 0.01498 0.01147 H1 2 0.374595 0.329375 0.826716 11.00000 -1.50000 F1 6 0.372988 0.570590 0.399377 11.00000 0.03556 0.05567 = 0.02454 -0.00664 0.00323 -0.00746 F2 6 0.361253 0.792916 0.435982 11.00000 0.03694 0.04523 = 0.03742 0.00539 -0.00325 -0.00480 C1 1 0.269316 0.582559 0.428490 11.00000 0.02834 0.05108 = 0.03347 0.00515 -0.00029 0.00303 C2 1 0.238755 0.514683 0.459889 11.00000 0.02851 0.07938 = 0.04597 0.01240 0.00317 -0.00338 AFIX 43 H2 2 0.201776 0.497228 0.443379 11.00000 -1.20000 AFIX 0 C3 1 0.270462 0.477369 0.518102 11.00000 0.03327 0.06715 = 0.04032 0.00864 0.00601 -0.00433 C4 1 0.322538 0.521423 0.522786 11.00000 0.02715 0.04954 = 0.02942 0.00103 0.00540 0.00112 C5 1 0.371274 0.504560 0.570195 11.00000 0.02919 0.03921 = 0.02567 -0.00313 0.00514 0.00082 C6 1 0.418122 0.550198 0.561783 11.00000 0.03179 0.03527 = 0.02480 -0.00219 0.00403 0.00161 C7 1 0.471788 0.552267 0.602782 11.00000 0.03428 0.03786 = 0.02645 -0.00336 0.00077 0.00617 C8 1 0.500750 0.621443 0.571904 11.00000 0.02748 0.04431 = 0.03187 -0.00359 -0.00138 0.00090 AFIX 43 H8 2 0.537830 0.637840 0.587543 11.00000 -1.20000 AFIX 0 C9 1 0.466966 0.664838 0.513058 11.00000 0.02578 0.04028 = 0.02848 -0.00819 0.00108 -0.00170 C10 1 0.478637 0.749876 0.466801 11.00000 0.02809 0.04823 = 0.02584 -0.00688 0.00261 -0.00381 AFIX 43 H10 2 0.452719 0.753131 0.426816 11.00000 -1.20000 AFIX 0 C11 1 0.523205 0.825165 0.475467 11.00000 0.03082 0.04925 = 0.02870 -0.00717 0.00224 -0.00102 AFIX 43 H11 2 0.549963 0.814476 0.514574 11.00000 -1.20000 AFIX 0 C12 1 0.535006 0.921613 0.431351 11.00000 0.02338 0.04166 = 0.03491 -0.01267 0.00738 -0.00038 C13 1 0.582044 1.001957 0.448670 11.00000 0.03239 0.04372 = 0.04518 -0.01305 0.00979 -0.00107 AFIX 43 H13 2 0.606595 0.990893 0.489218 11.00000 -1.20000 AFIX 0 C14 1 0.593434 1.097182 0.407822 11.00000 0.04007 0.03839 = 0.06688 -0.01448 0.02210 -0.00461 AFIX 43 H14 2 0.625885 1.149586 0.420241 11.00000 -1.20000 AFIX 0 C15 1 0.558302 1.116306 0.349740 11.00000 0.05489 0.04872 = 0.05376 0.00172 0.02505 0.00016 AFIX 43 H15 2 0.566043 1.182299 0.321758 11.00000 -1.20000 AFIX 0 C16 1 0.511374 1.038919 0.331947 11.00000 0.04781 0.06264 = 0.04237 0.00206 0.01240 -0.00388 AFIX 43 H16 2 0.486855 1.052454 0.291537 11.00000 -1.20000 AFIX 0 C17 1 0.499577 0.942778 0.371685 11.00000 0.03221 0.05286 = 0.03828 -0.00675 0.00882 -0.00405 AFIX 43 H17 2 0.467136 0.890357 0.358528 11.00000 -1.20000 AFIX 0 C18 1 0.254786 0.638803 0.366518 11.00000 0.03091 0.05187 = 0.03470 0.00598 0.00346 0.00144 AFIX 43 H18 2 0.279226 0.699959 0.355912 11.00000 -1.20000 AFIX 0 C19 1 0.208642 0.609367 0.323113 11.00000 0.03065 0.04884 = 0.03916 0.00758 0.00213 -0.00091 AFIX 43 H19 2 0.183838 0.553462 0.335405 11.00000 -1.20000 AFIX 0 C20 1 0.192872 0.655031 0.258752 11.00000 0.03049 0.03699 = 0.03483 0.00498 0.00043 0.00411 C21 1 0.143935 0.613142 0.218713 11.00000 0.03918 0.06501 = 0.04439 0.01761 -0.00630 -0.01100 AFIX 43 H21 2 0.121044 0.556736 0.233979 11.00000 -1.20000 AFIX 0 C22 1 0.127857 0.651777 0.157175 11.00000 0.04738 0.07207 = 0.04321 0.01306 -0.01181 -0.01030 AFIX 43 H22 2 0.094446 0.619645 0.130361 11.00000 -1.20000 AFIX 0 C23 1 0.159154 0.735267 0.134292 11.00000 0.04455 0.04950 = 0.03281 0.00777 0.00199 0.00580 AFIX 43 H23 2 0.147558 0.763458 0.091964 11.00000 -1.20000 AFIX 0 C24 1 0.207899 0.778385 0.173342 11.00000 0.04732 0.05120 = 0.04476 0.00363 0.01753 -0.00240 AFIX 43 H24 2 0.230304 0.835890 0.157747 11.00000 -1.20000 AFIX 0 C25 1 0.224349 0.739280 0.234279 11.00000 0.03595 0.04765 = 0.04062 -0.00162 0.00217 -0.00035 AFIX 43 H25 2 0.258110 0.770442 0.260531 11.00000 -1.20000 AFIX 0 C26 1 0.493827 0.495234 0.667293 11.00000 0.03928 0.06606 = 0.03298 0.00423 -0.00577 0.00198 AFIX 137 H26A 2 0.494956 0.388080 0.666399 11.00000 -1.50000 H26B 2 0.471321 0.526676 0.691232 11.00000 -1.50000 H26C 2 0.529682 0.533476 0.686631 11.00000 -1.50000 AFIX 0 C27 1 0.251072 0.403228 0.564655 11.00000 0.03919 0.10317 = 0.05344 0.01947 0.01151 -0.01081 AFIX 137 H27A 2 0.251076 0.472972 0.597222 11.00000 -1.50000 H27B 2 0.274356 0.320774 0.582972 11.00000 -1.50000 H27C 2 0.215039 0.367197 0.544376 11.00000 -1.50000 AFIX 0 C28 1 0.371844 0.442522 0.630455 11.00000 0.02768 0.03714 = 0.02757 0.00182 0.00280 0.00130 C29 1 0.358291 0.526532 0.672808 11.00000 0.03798 0.04087 = 0.03128 0.00278 0.00524 0.00851 AFIX 43 H29 2 0.346982 0.624560 0.662542 11.00000 -1.20000 AFIX 0 C30 1 0.360733 0.471811 0.729787 11.00000 0.03924 0.04832 = 0.03011 -0.00152 0.00852 0.00865 AFIX 43 H30 2 0.350694 0.531226 0.758184 11.00000 -1.20000 AFIX 0 C31 1 0.377900 0.329713 0.745497 11.00000 0.03385 0.04398 = 0.02585 0.00397 0.00589 0.00047 C32 1 0.391480 0.244558 0.703651 11.00000 0.05324 0.03562 = 0.03985 0.00556 0.01565 0.00825 AFIX 43 H32 2 0.402759 0.146545 0.714013 11.00000 -1.20000 AFIX 0 C33 1 0.388904 0.299833 0.646892 11.00000 0.05262 0.04332 = 0.03338 -0.00450 0.01594 0.00691 AFIX 43 H33 2 0.398869 0.240066 0.618542 11.00000 -1.20000 AFIX 0 HKLF 4 REM 18gtu172_ET1_bas_0m in C2/c REM R1 = 0.0668 for 3015 Fo > 4sig(Fo) and 0.1025 for all 4646 data REM 357 parameters refined using 1 restraints END WGHT 0.0684 3.5874 REM Highest difference peak 0.230, deepest hole -0.346, 1-sigma level 0.059 Q1 1 0.4232 0.5467 0.4586 11.00000 0.05 0.23 ; _shelx_res_checksum 50774 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags_adp _atom_site_refinement_flags_posn _atom_site_occupancy B B1 0.36771(13) 0.6448(4) 0.45089(14) 0.0333(8) Uani d . . 1 N N1 0.41765(9) 0.6180(3) 0.50709(9) 0.0323(6) Uani d . . 1 N N2 0.32067(9) 0.5861(3) 0.46708(10) 0.0354(6) Uani d . . 1 O O1 0.38190(10) 0.2683(2) 0.80103(9) 0.0491(6) Uani d . D 1 H H1 0.3746(15) 0.329(3) 0.8267(14) 0.074 Uiso d U D 1 F F1 0.37299(6) 0.57059(19) 0.39938(6) 0.0402(5) Uani d . . 1 F F2 0.36125(7) 0.79292(18) 0.43598(7) 0.0436(5) Uani d . . 1 C C1 0.26932(12) 0.5826(3) 0.42849(13) 0.0402(8) Uani d . . 1 C C2 0.23876(13) 0.5147(4) 0.45989(15) 0.0535(10) Uani d . . 1 H H2 0.2018 0.4972 0.4434 0.064 Uiso calc U R 1 C C3 0.27046(13) 0.4774(4) 0.51810(14) 0.0484(9) Uani d . . 1 C C4 0.32254(12) 0.5214(3) 0.52279(12) 0.0363(7) Uani d . . 1 C C5 0.37127(11) 0.5046(3) 0.57020(12) 0.0323(7) Uani d . . 1 C C6 0.41812(12) 0.5502(3) 0.56178(12) 0.0319(7) Uani d . . 1 C C7 0.47179(12) 0.5523(3) 0.60278(12) 0.0351(7) Uani d . . 1 C C8 0.50075(12) 0.6214(3) 0.57190(13) 0.0373(8) Uani d . . 1 H H8 0.5378 0.6378 0.5875 0.045 Uiso calc U R 1 C C9 0.46697(11) 0.6648(3) 0.51306(12) 0.0334(7) Uani d . . 1 C C10 0.47864(12) 0.7499(3) 0.46680(12) 0.0356(7) Uani d . . 1 H H10 0.4527 0.7531 0.4268 0.043 Uiso calc U R 1 C C11 0.52320(12) 0.8252(3) 0.47547(13) 0.0381(8) Uani d . . 1 H H11 0.55 0.8145 0.5146 0.046 Uiso calc U R 1 C C12 0.53501(11) 0.9216(3) 0.43135(13) 0.0338(7) Uani d . . 1 C C13 0.58204(13) 1.0020(3) 0.44867(14) 0.0411(8) Uani d . . 1 H H13 0.6066 0.9909 0.4892 0.049 Uiso calc U R 1 C C14 0.59343(13) 1.0972(3) 0.40782(16) 0.0473(9) Uani d . . 1 H H14 0.6259 1.1496 0.4202 0.057 Uiso calc U R 1 C C15 0.55830(14) 1.1163(4) 0.34974(16) 0.0507(9) Uani d . . 1 H H15 0.566 1.1823 0.3218 0.061 Uiso calc U R 1 C C16 0.51137(14) 1.0389(4) 0.33195(15) 0.0515(9) Uani d . . 1 H H16 0.4869 1.0525 0.2915 0.062 Uiso calc U R 1 C C17 0.49958(12) 0.9428(4) 0.37169(13) 0.0418(8) Uani d . . 1 H H17 0.4671 0.8904 0.3585 0.05 Uiso calc U R 1 C C18 0.25479(12) 0.6388(3) 0.36652(13) 0.0409(8) Uani d . . 1 H H18 0.2792 0.7 0.3559 0.049 Uiso calc U R 1 C C19 0.20864(12) 0.6094(3) 0.32311(13) 0.0418(8) Uani d . . 1 H H19 0.1838 0.5535 0.3354 0.05 Uiso calc U R 1 C C20 0.19287(12) 0.6550(3) 0.25875(13) 0.0366(8) Uani d . . 1 C C21 0.14393(13) 0.6131(4) 0.21871(15) 0.0544(10) Uani d . . 1 H H21 0.121 0.5567 0.234 0.065 Uiso calc U R 1 C C22 0.12786(15) 0.6518(4) 0.15717(15) 0.0607(11) Uani d . . 1 H H22 0.0944 0.6196 0.1304 0.073 Uiso calc U R 1 C C23 0.15915(13) 0.7353(4) 0.13429(14) 0.0449(9) Uani d . . 1 H H23 0.1476 0.7635 0.092 0.054 Uiso calc U R 1 C C24 0.20790(13) 0.7784(4) 0.17334(14) 0.0472(9) Uani d . . 1 H H24 0.2303 0.8359 0.1577 0.057 Uiso calc U R 1 C C25 0.22435(13) 0.7393(3) 0.23428(14) 0.0439(8) Uani d . . 1 H H25 0.2581 0.7704 0.2605 0.053 Uiso calc U R 1 C C26 0.49383(13) 0.4952(4) 0.66729(13) 0.0504(9) Uani d . . 1 H H26A 0.495 0.3881 0.6664 0.076 Uiso calc U R 1 H H26B 0.4713 0.5267 0.6912 0.076 Uiso calc U R 1 H H26C 0.5297 0.5335 0.6866 0.076 Uiso calc U R 1 C C27 0.25107(14) 0.4032(5) 0.56466(16) 0.0662(12) Uani d . . 1 H H27A 0.2511 0.473 0.5972 0.099 Uiso calc U R 1 H H27B 0.2744 0.3208 0.583 0.099 Uiso calc U R 1 H H27C 0.215 0.3672 0.5444 0.099 Uiso calc U R 1 C C28 0.37184(11) 0.4425(3) 0.63046(12) 0.0323(7) Uani d . . 1 C C29 0.35829(12) 0.5265(3) 0.67281(13) 0.0382(8) Uani d . . 1 H H29 0.347 0.6246 0.6625 0.046 Uiso calc U R 1 C C30 0.36073(12) 0.4718(3) 0.72979(13) 0.0399(8) Uani d . . 1 H H30 0.3507 0.5312 0.7582 0.048 Uiso calc U R 1 C C31 0.37790(12) 0.3297(3) 0.74550(12) 0.0355(7) Uani d . . 1 C C32 0.39148(13) 0.2446(3) 0.70365(14) 0.0428(8) Uani d . . 1 H H32 0.4028 0.1465 0.714 0.051 Uiso calc U R 1 C C33 0.38890(13) 0.2998(3) 0.64689(13) 0.0427(8) Uani d . . 1 H H33 0.3989 0.2401 0.6185 0.051 Uiso calc U R 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 B1 0.0274(19) 0.040(2) 0.0257(16) -0.0029(16) -0.0007(14) 0.0012(14) N1 0.0262(14) 0.0421(14) 0.0229(12) -0.0029(11) 0.0004(10) -0.0031(10) N2 0.0259(14) 0.0480(15) 0.0270(12) -0.0016(12) 0.0016(10) 0.0046(11) O1 0.0616(16) 0.0550(14) 0.0307(12) 0.0115(13) 0.0150(11) 0.0084(10) F1 0.0356(10) 0.0557(11) 0.0245(8) -0.0075(9) 0.0032(7) -0.0066(7) F2 0.0369(10) 0.0452(10) 0.0374(9) -0.0048(8) -0.0032(8) 0.0054(8) C1 0.0283(17) 0.0511(19) 0.0335(16) 0.0030(16) -0.0003(13) 0.0051(14) C2 0.0285(19) 0.079(3) 0.0460(19) -0.0034(18) 0.0032(15) 0.0124(18) C3 0.0333(19) 0.067(2) 0.0403(18) -0.0043(17) 0.0060(15) 0.0086(16) C4 0.0271(18) 0.0495(18) 0.0294(15) 0.0011(15) 0.0054(13) 0.0010(13) C5 0.0292(17) 0.0392(16) 0.0257(14) 0.0008(14) 0.0051(12) -0.0031(12) C6 0.0318(17) 0.0353(16) 0.0248(14) 0.0016(14) 0.0040(12) -0.0022(12) C7 0.0343(18) 0.0379(17) 0.0265(14) 0.0062(15) 0.0008(13) -0.0034(12) C8 0.0275(17) 0.0443(18) 0.0319(15) 0.0009(15) -0.0014(13) -0.0036(13) C9 0.0258(17) 0.0403(16) 0.0285(15) -0.0017(14) 0.0011(12) -0.0082(12) C10 0.0281(17) 0.0482(18) 0.0258(14) -0.0038(15) 0.0026(12) -0.0069(13) C11 0.0308(18) 0.0493(18) 0.0287(15) -0.0010(16) 0.0022(13) -0.0072(14) C12 0.0234(16) 0.0417(17) 0.0349(16) -0.0004(14) 0.0074(13) -0.0127(13) C13 0.0324(19) 0.0437(18) 0.0452(18) -0.0011(15) 0.0098(15) -0.0130(15) C14 0.040(2) 0.0384(18) 0.067(2) -0.0046(16) 0.0221(18) -0.0145(17) C15 0.055(2) 0.049(2) 0.054(2) 0.0002(19) 0.0250(18) 0.0017(16) C16 0.048(2) 0.063(2) 0.0424(18) -0.0039(19) 0.0124(16) 0.0021(17) C17 0.0322(18) 0.053(2) 0.0383(17) -0.0041(16) 0.0088(14) -0.0068(15) C18 0.0309(18) 0.0519(19) 0.0347(16) 0.0014(16) 0.0035(14) 0.0060(14) C19 0.0306(18) 0.0488(19) 0.0392(17) -0.0009(15) 0.0021(14) 0.0076(14) C20 0.0305(17) 0.0370(17) 0.0348(16) 0.0041(15) 0.0004(13) 0.0050(13) C21 0.039(2) 0.065(2) 0.0444(19) -0.0110(18) -0.0063(16) 0.0176(17) C22 0.047(2) 0.072(2) 0.0432(19) -0.010(2) -0.0118(17) 0.0131(18) C23 0.045(2) 0.0495(19) 0.0328(16) 0.0058(17) 0.0020(15) 0.0078(15) C24 0.047(2) 0.051(2) 0.0448(19) -0.0024(17) 0.0175(16) 0.0036(15) C25 0.0360(19) 0.0477(19) 0.0406(18) -0.0003(16) 0.0022(14) -0.0016(15) C26 0.039(2) 0.066(2) 0.0330(16) 0.0020(18) -0.0058(14) 0.0042(15) C27 0.039(2) 0.103(3) 0.053(2) -0.011(2) 0.0115(17) 0.019(2) C28 0.0277(16) 0.0371(17) 0.0276(14) 0.0013(14) 0.0028(12) 0.0018(12) C29 0.0380(19) 0.0409(17) 0.0313(15) 0.0085(15) 0.0052(13) 0.0028(13) C30 0.0392(19) 0.0483(19) 0.0301(15) 0.0087(16) 0.0085(14) -0.0015(14) C31 0.0338(18) 0.0440(18) 0.0259(14) 0.0005(15) 0.0059(13) 0.0040(13) C32 0.053(2) 0.0356(17) 0.0398(17) 0.0082(16) 0.0157(15) 0.0056(14) C33 0.053(2) 0.0433(18) 0.0334(16) 0.0069(17) 0.0159(15) -0.0045(14) 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' B B 0.0013 0.0007 '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 F2 B1 F1 107.6(2) F2 B1 N2 110.8(3) F1 B1 N2 110.6(2) F2 B1 N1 111.3(2) F1 B1 N1 109.0(3) N2 B1 N1 107.6(2) C9 N1 C6 109.2(2) C9 N1 B1 125.9(2) C6 N1 B1 124.8(2) C1 N2 C4 107.9(2) C1 N2 B1 126.0(2) C4 N2 B1 126.0(2) C31 O1 H1 113.(3) N2 C1 C2 108.2(2) N2 C1 C18 121.2(3) C2 C1 C18 130.6(3) C3 C2 C1 109.3(3) C3 C2 H2 125.4 C1 C2 H2 125.4 C2 C3 C4 106.5(3) C2 C3 C27 123.9(3) C4 C3 C27 129.6(3) N2 C4 C5 120.0(3) N2 C4 C3 108.1(2) C5 C4 C3 131.8(3) C6 C5 C4 120.7(3) C6 C5 C28 120.4(2) C4 C5 C28 118.9(3) N1 C6 C5 120.9(2) N1 C6 C7 107.1(3) C5 C6 C7 131.8(3) C8 C7 C6 106.6(2) C8 C7 C26 124.5(3) C6 C7 C26 128.9(3) C7 C8 C9 109.2(3) C7 C8 H8 125.4 C9 C8 H8 125.4 N1 C9 C8 107.9(3) N1 C9 C10 122.8(2) C8 C9 C10 129.3(3) C11 C10 C9 124.9(3) C11 C10 H10 117.5 C9 C10 H10 117.5 C10 C11 C12 126.7(3) C10 C11 H11 116.6 C12 C11 H11 116.6 C17 C12 C13 117.7(3) C17 C12 C11 122.1(3) C13 C12 C11 120.2(3) C14 C13 C12 121.1(3) C14 C13 H13 119.4 C12 C13 H13 119.4 C15 C14 C13 120.3(3) C15 C14 H14 119.8 C13 C14 H14 119.8 C14 C15 C16 119.4(3) C14 C15 H15 120.3 C16 C15 H15 120.3 C17 C16 C15 121.1(3) C17 C16 H16 119.5 C15 C16 H16 119.5 C16 C17 C12 120.4(3) C16 C17 H17 119.8 C12 C17 H17 119.8 C19 C18 C1 123.2(3) C19 C18 H18 118.4 C1 C18 H18 118.4 C18 C19 C20 125.9(3) C18 C19 H19 117.0 C20 C19 H19 117.0 C21 C20 C25 117.1(3) C21 C20 C19 119.3(3) C25 C20 C19 123.7(3) C22 C21 C20 121.1(3) C22 C21 H21 119.4 C20 C21 H21 119.4 C23 C22 C21 120.8(3) C23 C22 H22 119.6 C21 C22 H22 119.6 C22 C23 C24 119.0(3) C22 C23 H23 120.5 C24 C23 H23 120.5 C25 C24 C23 120.6(3) C25 C24 H24 119.7 C23 C24 H24 119.7 C24 C25 C20 121.5(3) C24 C25 H25 119.3 C20 C25 H25 119.3 C7 C26 H26A 109.5 C7 C26 H26B 109.5 H26A C26 H26B 109.5 C7 C26 H26C 109.5 H26A C26 H26C 109.5 H26B C26 H26C 109.5 C3 C27 H27A 109.5 C3 C27 H27B 109.5 H27A C27 H27B 109.5 C3 C27 H27C 109.5 H27A C27 H27C 109.5 H27B C27 H27C 109.5 C29 C28 C33 118.2(3) C29 C28 C5 121.0(3) C33 C28 C5 120.7(3) C28 C29 C30 121.5(3) C28 C29 H29 119.3 C30 C29 H29 119.3 C29 C30 C31 119.7(3) C29 C30 H30 120.2 C31 C30 H30 120.2 O1 C31 C32 117.4(3) O1 C31 C30 123.2(3) C32 C31 C30 119.5(3) C31 C32 C33 120.5(3) C31 C32 H32 119.7 C33 C32 H32 119.7 C32 C33 C28 120.7(3) C32 C33 H33 119.7 C28 C33 H33 119.7 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance B1 F2 1.393(4) B1 F1 1.405(4) B1 N2 1.521(4) B1 N1 1.540(4) N1 C9 1.351(4) N1 C6 1.392(3) N2 C1 1.369(4) N2 C4 1.390(4) O1 C31 1.360(3) O1 H1 0.877(10) C1 C2 1.397(5) C1 C18 1.436(4) C2 C3 1.367(4) C2 H2 0.95 C3 C4 1.420(4) C3 C27 1.491(5) C4 C5 1.405(4) C5 C6 1.393(4) C5 C28 1.485(4) C6 C7 1.435(4) C7 C8 1.363(4) C7 C26 1.492(4) C8 C9 1.410(4) C8 H8 0.95 C9 C10 1.427(4) C10 C11 1.334(4) C10 H10 0.95 C11 C12 1.450(4) C11 H11 0.95 C12 C17 1.397(4) C12 C13 1.398(4) C13 C14 1.381(5) C13 H13 0.95 C14 C15 1.364(4) C14 H14 0.95 C15 C16 1.381(5) C15 H15 0.95 C16 C17 1.373(4) C16 H16 0.95 C17 H17 0.95 C18 C19 1.334(4) C18 H18 0.95 C19 C20 1.453(4) C19 H19 0.95 C20 C21 1.384(4) C20 C25 1.387(4) C21 C22 1.376(4) C21 H21 0.95 C22 C23 1.358(5) C22 H22 0.95 C23 C24 1.375(4) C23 H23 0.95 C24 C25 1.364(4) C24 H24 0.95 C25 H25 0.95 C26 H26A 0.98 C26 H26B 0.98 C26 H26C 0.98 C27 H27A 0.98 C27 H27B 0.98 C27 H27C 0.98 C28 C29 1.374(4) C28 C33 1.392(4) C29 C30 1.377(4) C29 H29 0.95 C30 C31 1.385(4) C30 H30 0.95 C31 C32 1.371(4) C32 C33 1.373(4) C32 H32 0.95 C33 H33 0.95 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O1 H1 F1 6_566 0.877(10) 1.909(14) 2.762(3) 164.(4) 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 F2 B1 N1 C9 -52.8(4) F1 B1 N1 C9 65.7(4) N2 B1 N1 C9 -174.4(3) F2 B1 N1 C6 122.4(3) F1 B1 N1 C6 -119.2(3) N2 B1 N1 C6 0.8(4) F2 B1 N2 C1 61.4(4) F1 B1 N2 C1 -57.8(4) N1 B1 N2 C1 -176.7(3) F2 B1 N2 C4 -121.3(3) F1 B1 N2 C4 119.4(3) N1 B1 N2 C4 0.5(4) C4 N2 C1 C2 -0.3(4) B1 N2 C1 C2 177.4(3) C4 N2 C1 C18 -178.6(3) B1 N2 C1 C18 -0.9(5) N2 C1 C2 C3 0.7(4) C18 C1 C2 C3 178.8(3) C1 C2 C3 C4 -0.9(4) C1 C2 C3 C27 179.8(3) C1 N2 C4 C5 177.2(3) B1 N2 C4 C5 -0.5(4) C1 N2 C4 C3 -0.2(3) B1 N2 C4 C3 -177.9(3) C2 C3 C4 N2 0.7(4) C27 C3 C4 N2 180.0(4) C2 C3 C4 C5 -176.3(3) C27 C3 C4 C5 3.0(6) N2 C4 C5 C6 -0.9(4) C3 C4 C5 C6 175.8(3) N2 C4 C5 C28 176.7(3) C3 C4 C5 C28 -6.6(5) C9 N1 C6 C5 173.7(3) B1 N1 C6 C5 -2.2(4) C9 N1 C6 C7 -1.9(3) B1 N1 C6 C7 -177.8(3) C4 C5 C6 N1 2.2(4) C28 C5 C6 N1 -175.4(2) C4 C5 C6 C7 176.5(3) C28 C5 C6 C7 -1.0(5) N1 C6 C7 C8 0.7(3) C5 C6 C7 C8 -174.3(3) N1 C6 C7 C26 179.3(3) C5 C6 C7 C26 4.4(5) C6 C7 C8 C9 0.8(3) C26 C7 C8 C9 -178.0(3) C6 N1 C9 C8 2.4(3) B1 N1 C9 C8 178.2(3) C6 N1 C9 C10 -174.5(3) B1 N1 C9 C10 1.3(4) C7 C8 C9 N1 -2.0(3) C7 C8 C9 C10 174.6(3) N1 C9 C10 C11 164.5(3) C8 C9 C10 C11 -11.6(5) C9 C10 C11 C12 -174.9(3) C10 C11 C12 C17 -2.0(5) C10 C11 C12 C13 175.2(3) C17 C12 C13 C14 -1.0(4) C11 C12 C13 C14 -178.4(3) C12 C13 C14 C15 1.1(5) C13 C14 C15 C16 -0.4(5) C14 C15 C16 C17 -0.2(5) C15 C16 C17 C12 0.2(5) C13 C12 C17 C16 0.4(4) C11 C12 C17 C16 177.7(3) N2 C1 C18 C19 164.6(3) C2 C1 C18 C19 -13.3(6) C1 C18 C19 C20 -175.9(3) C18 C19 C20 C21 178.6(3) C18 C19 C20 C25 -1.3(5) C25 C20 C21 C22 1.0(5) C19 C20 C21 C22 -178.8(3) C20 C21 C22 C23 -1.6(6) C21 C22 C23 C24 1.4(6) C22 C23 C24 C25 -0.7(5) C23 C24 C25 C20 0.2(5) C21 C20 C25 C24 -0.4(5) C19 C20 C25 C24 179.5(3) C6 C5 C28 C29 99.8(3) C4 C5 C28 C29 -77.8(4) C6 C5 C28 C33 -76.7(4) C4 C5 C28 C33 105.7(3) C33 C28 C29 C30 -0.8(5) C5 C28 C29 C30 -177.4(3) C28 C29 C30 C31 0.9(5) C29 C30 C31 O1 179.3(3) C29 C30 C31 C32 -1.0(5) O1 C31 C32 C33 -179.4(3) C30 C31 C32 C33 1.0(5) C31 C32 C33 C28 -0.8(5) C29 C28 C33 C32 0.7(5) C5 C28 C33 C32 177.3(3)