#------------------------------------------------------------------------------ #$Date: 2026-06-03 23:54:34 +0100 (Wed, 03 Jun 2026) $ #$Revision: 306181 $ #$URL: svn://www.crystallography.net/cod/cif/7/72/10/7721076.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_7721076 loop_ _publ_author_name 'Niessen, Nicolas' 'Adjieufack, Abel Idrice' 'Tumanov, Nikolay' 'Wouters, Johan' 'Champagne, Beno\^it' 'Berionni, Guillaume' 'Bijouard, Kajetan' _publ_section_title ; Accessing chiral NHC-boranes by abstraction of C6F5 from the B(C6F5)4− weakly coordinating anion ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D5DT02919H _journal_year 2026 _chemical_formula_moiety 'C23 H16 B F5 N2' _chemical_formula_sum 'C23 H16 B F5 N2' _chemical_formula_weight 426.19 _chemical_name_common ; cis-1-methyl-10-(perfluorophenyl)-5-phenyl-5,10-dihydrobenzo[d]imidazo [1,2-a][1,3]azaborinin-1-ium-10-uide ; _chemical_name_systematic ; cis-1-methyl-10-(perfluorophenyl)-5-phenyl-5,10-dihydrobenzo[d]imidazo [1,2-a][1,3]azaborinin-1-ium-10-uide ; _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 difmap _atom_sites_solution_primary dual _atom_sites_solution_secondary dual _audit_creation_method SHELXL-2019/3 _audit_update_record ; 2025-10-16 deposited with the CCDC. 2026-05-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 106.4810(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.84660(10) _cell_length_b 12.4844(2) _cell_length_c 15.0059(2) _cell_measurement_reflns_used 9877 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 68.3635 _cell_measurement_theta_min 4.2507 _cell_volume 1948.51(5) _computing_cell_refinement 'APEX5 v2023.9-2 (Bruker AXS)' _computing_data_collection 'Bruker Instrument Service v8.5.1.2' _computing_data_reduction 'APEX5 v2023.9-2 (Bruker AXS)' _computing_structure_refinement 'SHELXL-2019/3 (Sheldrick, 2019)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 7.39 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method '\f and \w-scans' _diffrn_radiation_monochromator 'multilayer mirror' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_unetI/netI 0.0190 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.996 _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 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 34162 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.367 _diffrn_reflns_theta_min 4.251 _exptl_absorpt_coefficient_mu 1.017 _exptl_absorpt_correction_T_max 0.92 _exptl_absorpt_correction_T_min 0.80 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). "Comparison of silver and molybdenum microfocus X-ray sources for single-crystal structure determination" J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985 ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.453 _exptl_crystal_description block _exptl_crystal_F_000 872 _exptl_crystal_size_max 0.150 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_min 0.087 _refine_diff_density_max 0.339 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.053 _refine_ls_extinction_coef 0.0032(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/2 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 285 _refine_ls_number_reflns 3554 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.055 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0349 _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^)+(0.0457P)^2^+0.9426P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0896 _refine_ls_wR_factor_ref 0.0905 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3432 _reflns_number_total 3554 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5dt02919h2.cif _cod_data_source_block nt1560_KB454_2_100K _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7721076 _shelx_shelxl_version_number 2019/3 _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. ; _shelx_estimated_absorpt_t_min 0.862 _shelx_estimated_absorpt_t_max 0.917 _shelx_res_file ; TITL cu_nt1560_KB454_2_100K_a.res in P2(1)/c nt1560_KB454_2_100K.res created by SHELXL-2019/3 at 16:56:23 on 13-Nov-2024 REM Old TITL cu_nt1560_KB454_2_100K in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.145, Rweak 0.004, Alpha 0.017 REM 0.940 for 187 systematic absences, Orientation as input REM Formula found by SHELXT: C23 B F5 N2 CELL 1.54178 10.8466 12.4844 15.0059 90.000 106.481 90.000 ZERR 4.000 0.0001 0.0002 0.0002 0.000 0.001 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H B F N UNIT 92 64 4 20 8 ACTA CONF LIST 4 TEMP -173 SIZE 0.087 0.14 0.15 L.S. 10 BOND $H FMAP 2 PLAN 20 WGHT 0.045700 0.942600 EXTI 0.003249 FVAR 0.44271 F1 4 0.957097 0.411186 0.271342 11.00000 0.02290 0.03474 = 0.04281 0.00814 0.01381 0.00940 F2 4 1.065138 0.343944 0.445062 11.00000 0.02085 0.02894 = 0.05334 0.01022 -0.00671 0.00333 F3 4 0.937605 0.363943 0.576863 11.00000 0.04483 0.03821 = 0.02511 0.01095 -0.01172 -0.00598 F4 4 0.703694 0.460795 0.533080 11.00000 0.04792 0.04080 = 0.01979 0.00197 0.01147 -0.00662 F5 4 0.592484 0.526863 0.358752 11.00000 0.02430 0.02738 = 0.02408 0.00258 0.01008 0.00447 N1 5 0.512135 0.650867 0.150097 11.00000 0.01766 0.01428 = 0.01614 0.00082 0.00601 0.00141 N2 5 0.686624 0.723029 0.232748 11.00000 0.01994 0.01660 = 0.02030 0.00041 0.00582 -0.00158 C1 1 0.179914 0.609878 0.033155 11.00000 0.02222 0.01965 = 0.02318 -0.00153 0.00571 0.00121 AFIX 43 H1 2 0.188537 0.617296 -0.027800 11.00000 -1.20000 AFIX 0 C2 1 0.059184 0.617690 0.047810 11.00000 0.01859 0.02336 = 0.03947 -0.00555 0.00432 0.00050 AFIX 43 H2 2 -0.014547 0.629978 -0.003250 11.00000 -1.20000 AFIX 0 C3 1 0.046200 0.607617 0.136507 11.00000 0.02147 0.02674 = 0.05001 -0.00854 0.01939 -0.00362 AFIX 43 H3 2 -0.036440 0.612335 0.146238 11.00000 -1.20000 AFIX 0 C4 1 0.154141 0.590589 0.211390 11.00000 0.03349 0.02505 = 0.03417 -0.00514 0.02147 -0.00459 AFIX 43 H4 2 0.145345 0.584571 0.272401 11.00000 -1.20000 AFIX 0 C5 1 0.274744 0.582367 0.197148 11.00000 0.02455 0.01841 = 0.02205 -0.00144 0.00996 -0.00086 AFIX 43 H5 2 0.348387 0.570694 0.248418 11.00000 -1.20000 AFIX 0 C6 1 0.287974 0.591221 0.107649 11.00000 0.01835 0.01244 = 0.02201 -0.00157 0.00808 0.00016 C7 1 0.418460 0.576795 0.090408 11.00000 0.01677 0.01630 = 0.01356 0.00054 0.00439 0.00102 AFIX 13 H7 2 0.408631 0.598436 0.024593 11.00000 -1.20000 AFIX 0 C8 1 0.463466 0.460430 0.100066 11.00000 0.02010 0.01640 = 0.01351 0.00078 0.00849 0.00074 C9 1 0.373911 0.384559 0.051913 11.00000 0.02006 0.02120 = 0.01722 -0.00037 0.00626 0.00003 AFIX 43 H9 2 0.289086 0.406719 0.019981 11.00000 -1.20000 AFIX 0 C10 1 0.407518 0.277639 0.050288 11.00000 0.02754 0.01887 = 0.02031 -0.00299 0.00900 -0.00417 AFIX 43 H10 2 0.346400 0.226841 0.017085 11.00000 -1.20000 AFIX 0 C11 1 0.531580 0.245325 0.097719 11.00000 0.03142 0.01436 = 0.02135 0.00141 0.01249 0.00249 AFIX 43 H11 2 0.555891 0.172298 0.096985 11.00000 -1.20000 AFIX 0 C12 1 0.619369 0.320407 0.146011 11.00000 0.02316 0.01837 = 0.01662 0.00301 0.00825 0.00347 AFIX 43 H12 2 0.703283 0.297096 0.178996 11.00000 -1.20000 AFIX 0 C13 1 0.589191 0.429894 0.148159 11.00000 0.02111 0.01721 = 0.01275 0.00244 0.00854 0.00179 C14 1 0.769707 0.474037 0.306507 11.00000 0.01775 0.01359 = 0.02159 0.00102 0.00297 -0.00217 C15 1 0.889566 0.425000 0.333479 11.00000 0.01923 0.01826 = 0.02955 0.00230 0.00553 -0.00120 C16 1 0.947102 0.388173 0.422683 11.00000 0.01829 0.01749 = 0.03805 0.00497 -0.00537 -0.00136 C17 1 0.883778 0.399166 0.489697 11.00000 0.03199 0.02126 = 0.02138 0.00578 -0.00670 -0.00747 C18 1 0.765040 0.448032 0.467391 11.00000 0.03183 0.02139 = 0.02019 0.00008 0.00453 -0.00846 C19 1 0.711145 0.482950 0.377444 11.00000 0.01981 0.01567 = 0.02140 0.00046 0.00247 -0.00216 C20 1 0.487305 0.759001 0.156298 11.00000 0.02378 0.01488 = 0.02263 0.00162 0.00816 0.00427 AFIX 43 H20 2 0.408263 0.794645 0.128821 11.00000 -1.20000 AFIX 0 C21 1 0.596418 0.803756 0.208604 11.00000 0.02790 0.01344 = 0.02426 -0.00058 0.00922 0.00089 AFIX 43 H21 2 0.609105 0.877062 0.225734 11.00000 -1.20000 AFIX 0 C22 1 0.634844 0.628909 0.196741 11.00000 0.01801 0.01726 = 0.01493 0.00216 0.00686 -0.00105 C23 1 0.818357 0.737519 0.291223 11.00000 0.02163 0.02440 = 0.03032 -0.00208 0.00248 -0.00489 AFIX 137 H23A 2 0.873768 0.682701 0.275939 11.00000 -1.50000 H23B 2 0.820554 0.730844 0.356726 11.00000 -1.50000 H23C 2 0.849146 0.808736 0.280240 11.00000 -1.50000 AFIX 0 B1 3 0.699684 0.513332 0.200037 11.00000 0.01741 0.01701 = 0.01857 0.00239 0.00723 0.00219 H1B 2 0.775195 0.520975 0.161130 11.00000 -1.50000 REM REM C:/work/single_crystal/nt1560_KB454_2_100K/structure/nt1560_KB454_2_10= REM =0K.hkl REM HKLF 4 REM cu_nt1560_KB454_2_100K_a.res in P2(1)/c REM wR2 = 0.0905, GooF = S = 1.055, Restrained GooF = 1.055 for all data REM R1 = 0.0349 for 3432 Fo > 4sig(Fo) and 0.0357 for all 3554 data REM 285 parameters refined using 0 restraints END WGHT 0.0457 0.9426 REM Highest difference peak 0.339, deepest hole -0.235, 1-sigma level 0.053 Q1 1 0.6401 0.4705 0.1715 11.00000 0.05 0.34 Q2 1 0.3570 0.5880 0.1039 11.00000 0.05 0.32 Q3 1 0.6736 0.5753 0.2023 11.00000 0.05 0.31 Q4 1 0.7294 0.4960 0.2524 11.00000 0.05 0.28 Q5 1 0.4450 0.5173 0.0974 11.00000 0.05 0.27 Q6 1 1.0813 0.3290 0.3888 11.00000 0.05 0.27 Q7 1 0.7473 0.7347 0.2492 11.00000 0.05 0.26 Q8 1 0.9001 0.3842 0.3724 11.00000 0.05 0.26 Q9 1 0.6022 0.3838 0.1545 11.00000 0.05 0.24 Q10 1 0.4690 0.6120 0.1196 11.00000 0.05 0.23 Q11 1 0.5316 0.4527 0.1183 11.00000 0.05 0.23 Q12 1 0.8156 0.4346 0.3178 11.00000 0.05 0.23 Q13 1 0.9978 0.3463 0.5472 11.00000 0.05 0.22 Q14 1 0.9344 0.4384 0.3922 11.00000 0.05 0.22 Q15 1 0.8360 0.4691 0.3279 11.00000 0.05 0.21 Q16 1 0.8648 0.6685 0.3132 11.00000 0.05 0.21 Q17 1 0.5533 0.7942 0.1550 11.00000 0.05 0.20 Q18 1 0.6542 0.7619 0.2161 11.00000 0.05 0.20 Q19 1 0.3849 0.3347 0.0632 11.00000 0.05 0.20 Q20 1 0.4090 0.4215 0.0911 11.00000 0.05 0.19 ; _shelx_res_checksum 85054 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 F1 F 0.95710(7) 0.41119(7) 0.27134(6) 0.0326(2) Uani 1 1 d . . . . . F2 F 1.06514(7) 0.34394(7) 0.44506(7) 0.0379(2) Uani 1 1 d . . . . . F3 F 0.93760(9) 0.36394(7) 0.57686(6) 0.0405(2) Uani 1 1 d . . . . . F4 F 0.70369(9) 0.46080(7) 0.53308(5) 0.0358(2) Uani 1 1 d . . . . . F5 F 0.59248(7) 0.52686(6) 0.35875(5) 0.02459(19) Uani 1 1 d . . . . . N1 N 0.51213(9) 0.65087(8) 0.15010(7) 0.0158(2) Uani 1 1 d . . . . . N2 N 0.68662(10) 0.72303(8) 0.23275(7) 0.0189(2) Uani 1 1 d . . . . . C1 C 0.17991(12) 0.60988(10) 0.03315(9) 0.0218(3) Uani 1 1 d . . . . . H1 H 0.188537 0.617296 -0.027800 0.026 Uiso 1 1 calc R U . . . C2 C 0.05918(13) 0.61769(11) 0.04781(10) 0.0279(3) Uani 1 1 d . . . . . H2 H -0.014547 0.629978 -0.003250 0.034 Uiso 1 1 calc R U . . . C3 C 0.04620(13) 0.60762(11) 0.13651(11) 0.0308(3) Uani 1 1 d . . . . . H3 H -0.036440 0.612335 0.146238 0.037 Uiso 1 1 calc R U . . . C4 C 0.15414(14) 0.59059(11) 0.21139(10) 0.0285(3) Uani 1 1 d . . . . . H4 H 0.145345 0.584571 0.272401 0.034 Uiso 1 1 calc R U . . . C5 C 0.27474(12) 0.58237(10) 0.19715(9) 0.0210(3) Uani 1 1 d . . . . . H5 H 0.348387 0.570694 0.248418 0.025 Uiso 1 1 calc R U . . . C6 C 0.28797(11) 0.59122(9) 0.10765(8) 0.0171(3) Uani 1 1 d . . . . . C7 C 0.41846(11) 0.57679(9) 0.09041(8) 0.0155(2) Uani 1 1 d . . . . . H7 H 0.408631 0.598436 0.024593 0.019 Uiso 1 1 calc R U . . . C8 C 0.46347(11) 0.46043(9) 0.10007(8) 0.0159(2) Uani 1 1 d . . . . . C9 C 0.37391(12) 0.38456(10) 0.05191(8) 0.0193(3) Uani 1 1 d . . . . . H9 H 0.289086 0.406719 0.019981 0.023 Uiso 1 1 calc R U . . . C10 C 0.40752(13) 0.27764(10) 0.05029(9) 0.0218(3) Uani 1 1 d . . . . . H10 H 0.346400 0.226841 0.017085 0.026 Uiso 1 1 calc R U . . . C11 C 0.53158(13) 0.24533(10) 0.09772(9) 0.0213(3) Uani 1 1 d . . . . . H11 H 0.555891 0.172298 0.096985 0.026 Uiso 1 1 calc R U . . . C12 C 0.61937(12) 0.32041(10) 0.14601(8) 0.0188(3) Uani 1 1 d . . . . . H12 H 0.703283 0.297096 0.178996 0.023 Uiso 1 1 calc R U . . . C13 C 0.58919(11) 0.42989(9) 0.14816(8) 0.0163(2) Uani 1 1 d . . . . . C14 C 0.76971(11) 0.47404(9) 0.30651(8) 0.0182(3) Uani 1 1 d . . . . . C15 C 0.88957(12) 0.42500(10) 0.33348(9) 0.0226(3) Uani 1 1 d . . . . . C16 C 0.94710(12) 0.38817(10) 0.42268(10) 0.0274(3) Uani 1 1 d . . . . . C17 C 0.88378(14) 0.39917(11) 0.48970(9) 0.0278(3) Uani 1 1 d . . . . . C18 C 0.76504(13) 0.44803(11) 0.46739(9) 0.0251(3) Uani 1 1 d . . . . . C19 C 0.71115(12) 0.48295(10) 0.37744(9) 0.0197(3) Uani 1 1 d . . . . . C20 C 0.48731(12) 0.75900(10) 0.15630(9) 0.0201(3) Uani 1 1 d . . . . . H20 H 0.408263 0.794645 0.128821 0.024 Uiso 1 1 calc R U . . . C21 C 0.59642(12) 0.80376(10) 0.20860(9) 0.0215(3) Uani 1 1 d . . . . . H21 H 0.609105 0.877062 0.225734 0.026 Uiso 1 1 calc R U . . . C22 C 0.63484(11) 0.62891(9) 0.19674(8) 0.0163(3) Uani 1 1 d . . . . . C23 C 0.81836(12) 0.73752(11) 0.29122(10) 0.0265(3) Uani 1 1 d . . . . . H23A H 0.873768 0.682701 0.275939 0.040 Uiso 1 1 calc R U . . . H23B H 0.820554 0.730844 0.356726 0.040 Uiso 1 1 calc R U . . . H23C H 0.849146 0.808736 0.280240 0.040 Uiso 1 1 calc R U . . . B1 B 0.69968(13) 0.51333(11) 0.20004(9) 0.0172(3) Uani 1 1 d . . . . . H1B H 0.7752(15) 0.5210(13) 0.1611(11) 0.026 Uiso 1 1 d . 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 F1 0.0229(4) 0.0347(5) 0.0428(5) 0.0081(4) 0.0138(3) 0.0094(3) F2 0.0208(4) 0.0289(4) 0.0533(6) 0.0102(4) -0.0067(4) 0.0033(3) F3 0.0448(5) 0.0382(5) 0.0251(4) 0.0110(4) -0.0117(4) -0.0060(4) F4 0.0479(5) 0.0408(5) 0.0198(4) 0.0020(3) 0.0115(4) -0.0066(4) F5 0.0243(4) 0.0274(4) 0.0241(4) 0.0026(3) 0.0101(3) 0.0045(3) N1 0.0177(5) 0.0143(5) 0.0161(5) 0.0008(4) 0.0060(4) 0.0014(4) N2 0.0199(5) 0.0166(5) 0.0203(5) 0.0004(4) 0.0058(4) -0.0016(4) C1 0.0222(6) 0.0196(6) 0.0232(6) -0.0015(5) 0.0057(5) 0.0012(5) C2 0.0186(6) 0.0234(7) 0.0395(8) -0.0055(6) 0.0043(6) 0.0005(5) C3 0.0215(7) 0.0267(7) 0.0500(9) -0.0085(6) 0.0194(6) -0.0036(5) C4 0.0335(7) 0.0250(7) 0.0342(7) -0.0051(6) 0.0215(6) -0.0046(6) C5 0.0245(6) 0.0184(6) 0.0220(6) -0.0014(5) 0.0100(5) -0.0009(5) C6 0.0183(6) 0.0124(5) 0.0220(6) -0.0016(4) 0.0081(5) 0.0002(4) C7 0.0168(6) 0.0163(6) 0.0136(5) 0.0005(4) 0.0044(4) 0.0010(4) C8 0.0201(6) 0.0164(6) 0.0135(5) 0.0008(4) 0.0085(4) 0.0007(5) C9 0.0201(6) 0.0212(6) 0.0172(6) -0.0004(5) 0.0063(5) 0.0000(5) C10 0.0275(7) 0.0189(6) 0.0203(6) -0.0030(5) 0.0090(5) -0.0042(5) C11 0.0314(7) 0.0144(6) 0.0213(6) 0.0014(5) 0.0125(5) 0.0025(5) C12 0.0232(6) 0.0184(6) 0.0166(6) 0.0030(4) 0.0083(5) 0.0035(5) C13 0.0211(6) 0.0172(6) 0.0128(5) 0.0024(4) 0.0085(4) 0.0018(5) C14 0.0178(6) 0.0136(6) 0.0216(6) 0.0010(4) 0.0030(5) -0.0022(4) C15 0.0192(6) 0.0183(6) 0.0295(7) 0.0023(5) 0.0055(5) -0.0012(5) C16 0.0183(6) 0.0175(6) 0.0380(8) 0.0050(5) -0.0054(6) -0.0014(5) C17 0.0320(7) 0.0213(6) 0.0214(7) 0.0058(5) -0.0067(5) -0.0075(5) C18 0.0318(7) 0.0214(6) 0.0202(6) 0.0001(5) 0.0045(5) -0.0085(5) C19 0.0198(6) 0.0157(6) 0.0214(6) 0.0005(5) 0.0025(5) -0.0022(5) C20 0.0238(6) 0.0149(6) 0.0226(6) 0.0016(5) 0.0082(5) 0.0043(5) C21 0.0279(7) 0.0134(6) 0.0243(6) -0.0006(5) 0.0092(5) 0.0009(5) C22 0.0180(6) 0.0173(6) 0.0149(5) 0.0022(4) 0.0069(4) -0.0011(4) C23 0.0216(6) 0.0244(7) 0.0303(7) -0.0021(5) 0.0025(5) -0.0049(5) B1 0.0174(6) 0.0170(6) 0.0186(6) 0.0024(5) 0.0072(5) 0.0022(5) 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' B B 0.0090 0.0039 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C22 N1 C20 110.27(10) . . ? C22 N1 C7 126.74(10) . . ? C20 N1 C7 122.59(10) . . ? C22 N2 C21 110.36(10) . . ? C22 N2 C23 125.05(11) . . ? C21 N2 C23 124.57(11) . . ? C6 C1 C2 120.07(12) . . ? C6 C1 H1 120.0 . . ? C2 C1 H1 120.0 . . ? C3 C2 C1 120.20(13) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 119.96(12) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 120.09(13) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.09(12) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 119.58(11) . . ? C1 C6 C7 119.75(11) . . ? C5 C6 C7 120.64(11) . . ? N1 C7 C6 109.68(9) . . ? N1 C7 C8 113.12(9) . . ? C6 C7 C8 112.63(9) . . ? N1 C7 H7 107.0 . . ? C6 C7 H7 107.0 . . ? C8 C7 H7 107.0 . . ? C9 C8 C13 120.80(11) . . ? C9 C8 C7 115.98(10) . . ? C13 C8 C7 123.07(10) . . ? C10 C9 C8 120.85(12) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 119.42(12) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C12 C11 C10 119.53(11) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C13 122.62(11) . . ? C11 C12 H12 118.7 . . ? C13 C12 H12 118.7 . . ? C8 C13 C12 116.77(11) . . ? C8 C13 B1 123.64(11) . . ? C12 C13 B1 119.51(11) . . ? C15 C14 C19 113.91(11) . . ? C15 C14 B1 123.57(11) . . ? C19 C14 B1 122.47(10) . . ? F1 C15 C16 116.17(12) . . ? F1 C15 C14 120.08(11) . . ? C16 C15 C14 123.75(13) . . ? F2 C16 C17 119.67(12) . . ? F2 C16 C15 120.86(13) . . ? C17 C16 C15 119.45(12) . . ? F3 C17 C16 120.58(13) . . ? F3 C17 C18 119.91(14) . . ? C16 C17 C18 119.51(12) . . ? F4 C18 C17 119.78(12) . . ? F4 C18 C19 121.23(12) . . ? C17 C18 C19 118.99(13) . . ? F5 C19 C18 116.40(11) . . ? F5 C19 C14 119.21(11) . . ? C18 C19 C14 124.38(12) . . ? C21 C20 N1 106.80(11) . . ? C21 C20 H20 126.6 . . ? N1 C20 H20 126.6 . . ? C20 C21 N2 106.94(11) . . ? C20 C21 H21 126.5 . . ? N2 C21 H21 126.5 . . ? N1 C22 N2 105.63(10) . . ? N1 C22 B1 124.16(10) . . ? N2 C22 B1 130.13(10) . . ? N2 C23 H23A 109.5 . . ? N2 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N2 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 B1 C13 107.93(10) . . ? C22 B1 C14 112.24(10) . . ? C13 B1 C14 110.68(10) . . ? C22 B1 H1B 106.4(8) . . ? C13 B1 H1B 110.6(8) . . ? C14 B1 H1B 108.9(8) . . ? 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 F1 C15 1.3503(16) . ? F2 C16 1.3464(15) . ? F3 C17 1.3460(15) . ? F4 C18 1.3461(16) . ? F5 C19 1.3531(14) . ? N1 C22 1.3446(15) . ? N1 C20 1.3849(15) . ? N1 C7 1.4742(15) . ? N2 C22 1.3475(16) . ? N2 C21 1.3796(16) . ? N2 C23 1.4605(16) . ? C1 C6 1.3908(17) . ? C1 C2 1.3914(18) . ? C1 H1 0.9500 . ? C2 C3 1.383(2) . ? C2 H2 0.9500 . ? C3 C4 1.390(2) . ? C3 H3 0.9500 . ? C4 C5 1.3878(18) . ? C4 H4 0.9500 . ? C5 C6 1.3949(17) . ? C5 H5 0.9500 . ? C6 C7 1.5200(15) . ? C7 C8 1.5263(16) . ? C7 H7 1.0000 . ? C8 C9 1.4016(17) . ? C8 C13 1.4026(17) . ? C9 C10 1.3858(18) . ? C9 H9 0.9500 . ? C10 C11 1.3916(19) . ? C10 H10 0.9500 . ? C11 C12 1.3853(18) . ? C11 H11 0.9500 . ? C12 C13 1.4080(17) . ? C12 H12 0.9500 . ? C13 B1 1.6119(18) . ? C14 C15 1.3893(18) . ? C14 C19 1.3902(18) . ? C14 B1 1.6376(17) . ? C15 C16 1.3852(19) . ? C16 C17 1.376(2) . ? C17 C18 1.378(2) . ? C18 C19 1.3805(18) . ? C20 C21 1.3423(18) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 B1 1.5998(17) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? B1 H1B 1.137(15) . ? 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 C6 C1 C2 C3 0.4(2) . . . . ? C1 C2 C3 C4 0.6(2) . . . . ? C2 C3 C4 C5 -0.8(2) . . . . ? C3 C4 C5 C6 0.0(2) . . . . ? C2 C1 C6 C5 -1.16(18) . . . . ? C2 C1 C6 C7 176.70(11) . . . . ? C4 C5 C6 C1 0.94(18) . . . . ? C4 C5 C6 C7 -176.90(11) . . . . ? C22 N1 C7 C6 138.61(11) . . . . ? C20 N1 C7 C6 -49.37(14) . . . . ? C22 N1 C7 C8 11.95(16) . . . . ? C20 N1 C7 C8 -176.03(10) . . . . ? C1 C6 C7 N1 127.23(11) . . . . ? C5 C6 C7 N1 -54.93(14) . . . . ? C1 C6 C7 C8 -105.84(12) . . . . ? C5 C6 C7 C8 72.00(14) . . . . ? N1 C7 C8 C9 174.17(9) . . . . ? C6 C7 C8 C9 49.09(13) . . . . ? N1 C7 C8 C13 -10.35(15) . . . . ? C6 C7 C8 C13 -135.43(11) . . . . ? C13 C8 C9 C10 -0.29(17) . . . . ? C7 C8 C9 C10 175.30(11) . . . . ? C8 C9 C10 C11 0.48(18) . . . . ? C9 C10 C11 C12 0.19(18) . . . . ? C10 C11 C12 C13 -1.09(18) . . . . ? C9 C8 C13 C12 -0.55(16) . . . . ? C7 C8 C13 C12 -175.82(10) . . . . ? C9 C8 C13 B1 176.32(10) . . . . ? C7 C8 C13 B1 1.05(17) . . . . ? C11 C12 C13 C8 1.25(17) . . . . ? C11 C12 C13 B1 -175.75(11) . . . . ? C19 C14 C15 F1 179.99(11) . . . . ? B1 C14 C15 F1 2.60(18) . . . . ? C19 C14 C15 C16 -0.20(18) . . . . ? B1 C14 C15 C16 -177.59(12) . . . . ? F1 C15 C16 F2 1.66(18) . . . . ? C14 C15 C16 F2 -178.16(11) . . . . ? F1 C15 C16 C17 -179.78(11) . . . . ? C14 C15 C16 C17 0.4(2) . . . . ? F2 C16 C17 F3 -1.48(19) . . . . ? C15 C16 C17 F3 179.94(12) . . . . ? F2 C16 C17 C18 177.62(11) . . . . ? C15 C16 C17 C18 -1.0(2) . . . . ? F3 C17 C18 F4 0.33(19) . . . . ? C16 C17 C18 F4 -178.77(11) . . . . ? F3 C17 C18 C19 -179.58(11) . . . . ? C16 C17 C18 C19 1.31(19) . . . . ? F4 C18 C19 F5 -2.19(17) . . . . ? C17 C18 C19 F5 177.72(11) . . . . ? F4 C18 C19 C14 178.92(11) . . . . ? C17 C18 C19 C14 -1.17(19) . . . . ? C15 C14 C19 F5 -178.27(10) . . . . ? B1 C14 C19 F5 -0.85(17) . . . . ? C15 C14 C19 C18 0.59(18) . . . . ? B1 C14 C19 C18 178.01(11) . . . . ? C22 N1 C20 C21 -0.72(13) . . . . ? C7 N1 C20 C21 -173.91(10) . . . . ? N1 C20 C21 N2 0.67(13) . . . . ? C22 N2 C21 C20 -0.41(14) . . . . ? C23 N2 C21 C20 -178.83(11) . . . . ? C20 N1 C22 N2 0.46(13) . . . . ? C7 N1 C22 N2 173.29(10) . . . . ? C20 N1 C22 B1 -176.52(10) . . . . ? C7 N1 C22 B1 -3.68(17) . . . . ? C21 N2 C22 N1 -0.03(13) . . . . ? C23 N2 C22 N1 178.38(11) . . . . ? C21 N2 C22 B1 176.69(11) . . . . ? C23 N2 C22 B1 -4.90(19) . . . . ? N1 C22 B1 C13 -5.92(15) . . . . ? N2 C22 B1 C13 177.90(11) . . . . ? N1 C22 B1 C14 -128.14(11) . . . . ? N2 C22 B1 C14 55.67(16) . . . . ? C8 C13 B1 C22 6.94(15) . . . . ? C12 C13 B1 C22 -176.28(10) . . . . ? C8 C13 B1 C14 130.12(11) . . . . ? C12 C13 B1 C14 -53.09(14) . . . . ? C15 C14 B1 C22 -136.99(12) . . . . ? C19 C14 B1 C22 45.83(15) . . . . ? C15 C14 B1 C13 102.35(13) . . . . ? C19 C14 B1 C13 -74.82(14) . . . . ?