#------------------------------------------------------------------------------ #$Date: 2026-06-03 23:54:34 +0100 (Wed, 03 Jun 2026) $ #$Revision: 306181 $ #$URL: svn://www.crystallography.net/cod/cif/7/72/10/7721074.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_7721074 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 H18 B F5 N2' _chemical_formula_sum 'C23 H18 B F5 N2' _chemical_formula_weight 428.20 _chemical_name_common ; [N-benzhydryl-N'-methyl-imidazol-2-ylidene](dihydrydo)(pentafluorophenyl)borane ; _chemical_name_systematic ; [N-benzhydryl-N'-methyl-imidazol-2-ylidene](dihydrydo)(pentafluorophenyl)borane ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -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 117.6630(10) _cell_angle_beta 93.3560(10) _cell_angle_gamma 90.7410(10) _cell_formula_units_Z 2 _cell_length_a 7.29340(10) _cell_length_b 12.2741(2) _cell_length_c 13.0135(2) _cell_measurement_reflns_used 9817 _cell_measurement_temperature 297(2) _cell_measurement_theta_max 68.1829 _cell_measurement_theta_min 3.8454 _cell_volume 1028.97(3) _computing_cell_refinement 'SAINT V8.41 (Bruker AXS LLC)' _computing_data_collection 'Bruker Instrument Service v8.5.5.6' _computing_data_reduction 'SAINT V8.41 (Bruker AXS LLC)' _computing_structure_refinement 'SHELXL-2019/3 (Sheldrick, 2019)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 297(2) _diffrn_detector_area_resol_mean 7.39 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.995 _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 0.0355 _diffrn_reflns_av_unetI/netI 0.0264 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 44773 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.185 _diffrn_reflns_theta_min 3.845 _exptl_absorpt_coefficient_mu 0.963 _exptl_absorpt_correction_T_max 0.929 _exptl_absorpt_correction_T_min 0.717 _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 1.382 _exptl_crystal_description plate _exptl_crystal_F_000 440 _exptl_crystal_size_max 0.370 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.078 _refine_diff_density_max 0.328 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.054 _refine_ls_extinction_coef 0.0076(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/3 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 288 _refine_ls_number_reflns 3758 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.052 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0436 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0642P)^2^+0.2865P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1194 _refine_ls_wR_factor_ref 0.1212 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3579 _reflns_number_total 3758 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5dt02919h2.cif _cod_data_source_block nt1623_NiNi360_RT _cod_database_code 7721074 _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 0.717 _shelx_estimated_absorpt_t_max 0.929 _shelx_res_file ; TITL cu_nt1623_NiNi360_RT_a.res in P-1 nt1623_NiNi360_RT.res created by SHELXL-2019/3 at 20:48:26 on 31-Mar-2025 REM Old TITL cu_nt1623_NiNi360_RT in P-1 REM SHELXT solution in P-1: R1 0.193, Rweak 0.010, Alpha 0.038 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C23 B F5 N2 CELL 1.54178 7.2934 12.2741 13.0135 117.663 93.356 90.741 ZERR 2.000 0.0001 0.0002 0.0002 0.001 0.001 0.001 LATT 1 SFAC C H B F N UNIT 46 36 2 10 4 OMIT 0 1 0 TEMP 24 SIZE 0.078 0.20 0.37 L.S. 10 BOND $H LIST 4 ACTA CONf FMAP 2 PLAN 20 WGHT 0.064200 0.286500 EXTI 0.007591 FVAR 0.64683 F1 4 0.423250 0.701124 0.657084 11.00000 0.05935 0.07691 = 0.06664 0.04032 -0.01262 -0.02724 F2 4 0.472289 0.731405 0.873555 11.00000 0.07856 0.11770 = 0.08525 0.07538 0.00807 -0.00464 F3 4 0.695443 0.918955 1.035351 11.00000 0.10446 0.12059 = 0.04389 0.04097 -0.00132 0.02296 F4 4 0.867472 1.077407 0.974932 11.00000 0.10142 0.06604 = 0.05973 0.00733 -0.03459 -0.00611 F5 4 0.823433 1.047212 0.758488 11.00000 0.06201 0.05148 = 0.07029 0.02645 -0.01268 -0.01455 N1 5 0.277691 0.733505 0.437772 11.00000 0.03138 0.04000 = 0.03516 0.01661 0.00045 -0.00052 N2 5 0.236740 0.915105 0.573132 11.00000 0.03548 0.04095 = 0.03598 0.01588 0.00191 -0.00082 C1 1 0.621199 0.582151 0.226153 11.00000 0.04942 0.05694 = 0.05366 0.02281 0.01028 0.00642 AFIX 43 H1 2 0.677573 0.538038 0.260154 11.00000 -1.20000 AFIX 0 C2 1 0.702463 0.593621 0.137603 11.00000 0.06261 0.07515 = 0.06580 0.02539 0.02827 0.00983 AFIX 43 H2 2 0.813371 0.557195 0.112663 11.00000 -1.20000 AFIX 0 C3 1 0.620385 0.658341 0.086517 11.00000 0.08805 0.06371 = 0.05143 0.02326 0.02580 -0.00275 AFIX 43 H3 2 0.675619 0.665887 0.027368 11.00000 -1.20000 AFIX 0 C4 1 0.457120 0.711599 0.123048 11.00000 0.08796 0.05191 = 0.05121 0.02729 0.01310 0.00267 AFIX 43 H4 2 0.400713 0.754867 0.088171 11.00000 -1.20000 AFIX 0 C5 1 0.375267 0.701348 0.211942 11.00000 0.05879 0.04743 = 0.05005 0.02434 0.01108 0.00602 AFIX 43 H5 2 0.264839 0.738564 0.236829 11.00000 -1.20000 AFIX 0 C6 1 0.456448 0.636293 0.263832 11.00000 0.04271 0.03552 = 0.03868 0.01209 0.00397 -0.00378 C7 1 0.368411 0.620373 0.359160 11.00000 0.03701 0.03928 = 0.03959 0.01811 0.00256 0.00265 AFIX 13 H7 2 0.467813 0.607652 0.405958 11.00000 -1.20000 AFIX 0 C8 1 0.233342 0.509707 0.315175 11.00000 0.04236 0.03596 = 0.04925 0.01825 0.00892 0.00395 C9 1 0.147917 0.455596 0.204113 11.00000 0.05706 0.04718 = 0.05193 0.01936 -0.00006 -0.00718 AFIX 43 H9 2 0.173652 0.486577 0.153226 11.00000 -1.20000 AFIX 0 C10 1 0.023615 0.355113 0.167449 11.00000 0.06179 0.05225 = 0.07075 0.01513 -0.00261 -0.01209 AFIX 43 H10 2 -0.032895 0.319481 0.092486 11.00000 -1.20000 AFIX 0 C11 1 -0.015112 0.309088 0.241413 11.00000 0.05693 0.04499 = 0.09333 0.02124 0.01817 -0.00527 AFIX 43 H11 2 -0.098248 0.242211 0.217034 11.00000 -1.20000 AFIX 0 C12 1 0.068718 0.361554 0.351867 11.00000 0.07933 0.05554 = 0.08899 0.04080 0.03070 0.00087 AFIX 43 H12 2 0.042137 0.329971 0.402169 11.00000 -1.20000 AFIX 0 C13 1 0.193193 0.461654 0.389173 11.00000 0.06945 0.05274 = 0.05801 0.02928 0.01275 -0.00004 AFIX 43 H13 2 0.249665 0.496436 0.464118 11.00000 -1.20000 AFIX 0 C14 1 0.091829 0.753428 0.432221 11.00000 0.03058 0.04585 = 0.04615 0.02032 -0.00371 -0.00334 AFIX 43 H14 2 0.001515 0.698508 0.379529 11.00000 -1.20000 AFIX 0 C15 1 0.066813 0.866580 0.516969 11.00000 0.03129 0.04731 = 0.04811 0.02267 0.00220 0.00230 AFIX 43 H15 2 -0.044297 0.905208 0.534648 11.00000 -1.20000 AFIX 0 C16 1 0.270869 1.038533 0.670794 11.00000 0.05395 0.04541 = 0.04504 0.01019 0.00145 0.00081 AFIX 137 H16A 2 0.290760 1.032813 0.741677 11.00000 -1.50000 H16B 2 0.166470 1.087146 0.675778 11.00000 -1.50000 H16C 2 0.377784 1.076682 0.659051 11.00000 -1.50000 AFIX 0 C17 1 0.367216 0.833736 0.524637 11.00000 0.03342 0.04305 = 0.03233 0.01913 0.00125 -0.00185 C18 1 0.617014 0.874535 0.697492 11.00000 0.03187 0.04581 = 0.03996 0.01860 0.00015 0.00306 C19 1 0.534366 0.797477 0.734274 11.00000 0.03816 0.05741 = 0.04704 0.02625 -0.00018 -0.00002 C20 1 0.557830 0.810382 0.844992 11.00000 0.04985 0.07420 = 0.05426 0.03988 0.00730 0.00943 C21 1 0.670754 0.904482 0.926461 11.00000 0.06267 0.07505 = 0.04031 0.02812 0.00344 0.02074 C22 1 0.758199 0.983467 0.895936 11.00000 0.05619 0.04992 = 0.04325 0.00786 -0.01203 0.00960 C23 1 0.730852 0.966639 0.782869 11.00000 0.04137 0.04180 = 0.04728 0.01767 -0.00327 0.00363 B1 3 0.583748 0.855130 0.564987 11.00000 0.03075 0.05682 = 0.03933 0.02200 -0.00047 -0.00424 H1A 2 0.635692 0.942996 0.560347 11.00000 -1.50000 H1B 2 0.660034 0.772932 0.504438 11.00000 -1.50000 HKLF 4 REM cu_nt1623_NiNi360_RT_a.res in P-1 REM wR2 = 0.1212, GooF = S = 1.052, Restrained GooF = 1.052 for all data REM R1 = 0.0436 for 3579 Fo > 4sig(Fo) and 0.0450 for all 3758 data REM 288 parameters refined using 0 restraints END WGHT 0.0642 0.2865 REM Highest difference peak 0.328, deepest hole -0.266, 1-sigma level 0.054 Q1 1 0.7522 0.9980 1.0464 11.00000 0.05 0.33 Q2 1 0.5278 0.8170 0.9330 11.00000 0.05 0.27 Q3 1 0.4797 0.8386 0.5454 11.00000 0.05 0.25 Q4 1 0.9139 1.1294 0.9322 11.00000 0.05 0.24 Q5 1 0.5798 0.8805 0.8818 11.00000 0.05 0.23 Q6 1 0.3906 1.0467 0.7174 11.00000 0.05 0.23 Q7 1 0.3059 0.5617 0.3344 11.00000 0.05 0.22 Q8 1 0.4130 0.6370 0.3145 11.00000 0.05 0.21 Q9 1 0.2244 0.4628 0.2538 11.00000 0.05 0.20 Q10 1 0.5497 0.8531 0.7251 11.00000 0.05 0.20 Q11 1 0.5825 0.7844 0.7773 11.00000 0.05 0.20 Q12 1 0.6997 0.9939 0.8592 11.00000 0.05 0.20 Q13 1 0.2393 0.4721 0.3467 11.00000 0.05 0.19 Q14 1 0.6373 0.9411 0.7518 11.00000 0.05 0.19 Q15 1 0.1577 0.9002 0.5475 11.00000 0.05 0.19 Q16 1 0.1612 0.3986 0.3707 11.00000 0.05 0.19 Q17 1 0.6034 0.8669 0.6354 11.00000 0.05 0.18 Q18 1 0.2735 1.1090 0.6316 11.00000 0.05 0.18 Q19 1 0.1433 0.3889 0.4104 11.00000 0.05 0.17 Q20 1 0.4364 0.6875 0.2601 11.00000 0.05 0.17 ; _shelx_res_checksum 54872 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 _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.42325(14) 0.70112(10) 0.65708(9) 0.0660(3) Uani 1 1 d . . . . . F2 F 0.47229(17) 0.73141(13) 0.87355(11) 0.0827(4) Uani 1 1 d . . . . . F3 F 0.69544(19) 0.91896(14) 1.03535(9) 0.0887(4) Uani 1 1 d . . . . . F4 F 0.86747(19) 1.07741(11) 0.97493(10) 0.0863(4) Uani 1 1 d . . . . . F5 F 0.82343(14) 1.04721(9) 0.75849(9) 0.0630(3) Uani 1 1 d . . . . . N1 N 0.27769(14) 0.73351(10) 0.43777(9) 0.0360(3) Uani 1 1 d . . . . . N2 N 0.23674(15) 0.91510(10) 0.57313(10) 0.0383(3) Uani 1 1 d . . . . . C1 C 0.6212(2) 0.58215(16) 0.22615(15) 0.0542(4) Uani 1 1 d . . . . . H1 H 0.677573 0.538038 0.260154 0.065 Uiso 1 1 calc R U . . . C2 C 0.7025(3) 0.59362(19) 0.13760(18) 0.0697(5) Uani 1 1 d . . . . . H2 H 0.813371 0.557195 0.112663 0.084 Uiso 1 1 calc R U . . . C3 C 0.6204(3) 0.65834(18) 0.08652(16) 0.0683(5) Uani 1 1 d . . . . . H3 H 0.675619 0.665887 0.027368 0.082 Uiso 1 1 calc R U . . . C4 C 0.4571(3) 0.71160(16) 0.12305(15) 0.0620(5) Uani 1 1 d . . . . . H4 H 0.400713 0.754867 0.088171 0.074 Uiso 1 1 calc R U . . . C5 C 0.3753(2) 0.70135(14) 0.21194(14) 0.0511(4) Uani 1 1 d . . . . . H5 H 0.264839 0.738564 0.236829 0.061 Uiso 1 1 calc R U . . . C6 C 0.45645(19) 0.63629(12) 0.26383(12) 0.0410(3) Uani 1 1 d . . . . . C7 C 0.36841(18) 0.62037(12) 0.35916(12) 0.0387(3) Uani 1 1 d . . . . . H7 H 0.467813 0.607652 0.405958 0.046 Uiso 1 1 calc R U . . . C8 C 0.2333(2) 0.50971(12) 0.31517(13) 0.0429(3) Uani 1 1 d . . . . . C9 C 0.1479(2) 0.45560(15) 0.20411(15) 0.0538(4) Uani 1 1 d . . . . . H9 H 0.173652 0.486577 0.153226 0.065 Uiso 1 1 calc R U . . . C10 C 0.0236(3) 0.35511(17) 0.16745(18) 0.0674(5) Uani 1 1 d . . . . . H10 H -0.032895 0.319481 0.092486 0.081 Uiso 1 1 calc R U . . . C11 C -0.0151(3) 0.30909(16) 0.2414(2) 0.0689(5) Uani 1 1 d . . . . . H11 H -0.098248 0.242211 0.217034 0.083 Uiso 1 1 calc R U . . . C12 C 0.0687(3) 0.36155(17) 0.3519(2) 0.0707(5) Uani 1 1 d . . . . . H12 H 0.042137 0.329971 0.402169 0.085 Uiso 1 1 calc R U . . . C13 C 0.1932(3) 0.46165(16) 0.38917(16) 0.0584(4) Uani 1 1 d . . . . . H13 H 0.249665 0.496436 0.464118 0.070 Uiso 1 1 calc R U . . . C14 C 0.09183(18) 0.75343(13) 0.43222(13) 0.0416(3) Uani 1 1 d . . . . . H14 H 0.001515 0.698508 0.379529 0.050 Uiso 1 1 calc R U . . . C15 C 0.06681(18) 0.86658(13) 0.51697(13) 0.0421(3) Uani 1 1 d . . . . . H15 H -0.044297 0.905208 0.534648 0.051 Uiso 1 1 calc R U . . . C16 C 0.2709(2) 1.03853(14) 0.67079(14) 0.0526(4) Uani 1 1 d . . . . . H16A H 0.290760 1.032813 0.741677 0.079 Uiso 1 1 calc R U . . . H16B H 0.166470 1.087146 0.675778 0.079 Uiso 1 1 calc R U . . . H16C H 0.377784 1.076682 0.659051 0.079 Uiso 1 1 calc R U . . . C17 C 0.36722(17) 0.83374(12) 0.52464(11) 0.0357(3) Uani 1 1 d . . . . . C18 C 0.61701(18) 0.87453(13) 0.69749(12) 0.0399(3) Uani 1 1 d . . . . . C19 C 0.5344(2) 0.79748(15) 0.73427(13) 0.0469(4) Uani 1 1 d . . . . . C20 C 0.5578(2) 0.81038(17) 0.84499(15) 0.0553(4) Uani 1 1 d . . . . . C21 C 0.6708(3) 0.90448(18) 0.92646(14) 0.0587(4) Uani 1 1 d . . . . . C22 C 0.7582(2) 0.98347(15) 0.89594(14) 0.0559(4) Uani 1 1 d . . . . . C23 C 0.7309(2) 0.96664(13) 0.78287(13) 0.0450(3) Uani 1 1 d . . . . . B1 B 0.5837(2) 0.85513(17) 0.56499(14) 0.0427(4) Uani 1 1 d . . . . . H1A H 0.636(3) 0.9430(18) 0.5603(17) 0.064 Uiso 1 1 d . U . . . H1B H 0.660(3) 0.7729(18) 0.5044(17) 0.064 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 0.0593(6) 0.0769(7) 0.0666(6) 0.0403(5) -0.0126(5) -0.0272(5) F2 0.0786(7) 0.1177(10) 0.0852(8) 0.0754(8) 0.0081(6) -0.0046(7) F3 0.1045(9) 0.1206(10) 0.0439(6) 0.0410(6) -0.0013(6) 0.0230(8) F4 0.1014(9) 0.0660(7) 0.0597(7) 0.0073(5) -0.0346(6) -0.0061(6) F5 0.0620(6) 0.0515(5) 0.0703(6) 0.0265(5) -0.0127(5) -0.0145(4) N1 0.0314(5) 0.0400(6) 0.0352(6) 0.0166(5) 0.0005(4) -0.0005(4) N2 0.0355(6) 0.0409(6) 0.0360(6) 0.0159(5) 0.0019(4) -0.0008(4) C1 0.0494(9) 0.0569(9) 0.0537(9) 0.0228(8) 0.0103(7) 0.0064(7) C2 0.0626(11) 0.0752(12) 0.0658(11) 0.0254(10) 0.0283(9) 0.0098(9) C3 0.0881(14) 0.0637(11) 0.0514(10) 0.0233(9) 0.0258(9) -0.0027(10) C4 0.0880(13) 0.0519(9) 0.0512(9) 0.0273(8) 0.0131(9) 0.0027(9) C5 0.0588(9) 0.0474(8) 0.0500(9) 0.0243(7) 0.0111(7) 0.0060(7) C6 0.0427(7) 0.0355(7) 0.0387(7) 0.0121(6) 0.0040(6) -0.0038(5) C7 0.0370(7) 0.0393(7) 0.0396(7) 0.0181(6) 0.0026(5) 0.0027(5) C8 0.0424(7) 0.0360(7) 0.0492(8) 0.0183(6) 0.0089(6) 0.0040(6) C9 0.0571(9) 0.0472(8) 0.0519(9) 0.0194(7) -0.0001(7) -0.0072(7) C10 0.0618(11) 0.0522(10) 0.0707(12) 0.0151(9) -0.0026(9) -0.0121(8) C11 0.0569(10) 0.0450(9) 0.0933(15) 0.0212(9) 0.0182(10) -0.0053(7) C12 0.0793(13) 0.0555(10) 0.0890(14) 0.0408(10) 0.0307(11) 0.0009(9) C13 0.0695(11) 0.0527(9) 0.0580(10) 0.0293(8) 0.0128(8) 0.0000(8) C14 0.0306(6) 0.0459(7) 0.0461(8) 0.0203(6) -0.0037(5) -0.0033(5) C15 0.0313(6) 0.0473(8) 0.0481(8) 0.0227(6) 0.0022(5) 0.0023(5) C16 0.0540(9) 0.0454(8) 0.0450(8) 0.0102(7) 0.0015(7) 0.0008(7) C17 0.0334(6) 0.0431(7) 0.0323(6) 0.0191(5) 0.0013(5) -0.0018(5) C18 0.0319(6) 0.0458(7) 0.0400(7) 0.0186(6) 0.0001(5) 0.0031(5) C19 0.0382(7) 0.0574(9) 0.0470(8) 0.0263(7) -0.0002(6) 0.0000(6) C20 0.0499(9) 0.0742(11) 0.0543(9) 0.0399(9) 0.0073(7) 0.0094(8) C21 0.0627(10) 0.0751(11) 0.0403(8) 0.0281(8) 0.0034(7) 0.0207(9) C22 0.0562(9) 0.0499(9) 0.0432(8) 0.0079(7) -0.0120(7) 0.0096(7) C23 0.0414(7) 0.0418(7) 0.0473(8) 0.0177(6) -0.0033(6) 0.0036(6) B1 0.0308(7) 0.0568(10) 0.0393(8) 0.0220(7) -0.0005(6) -0.0042(7) 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 C17 N1 C14 110.08(11) . . ? C17 N1 C7 124.18(11) . . ? C14 N1 C7 125.72(11) . . ? C17 N2 C15 110.55(11) . . ? C17 N2 C16 124.77(12) . . ? C15 N2 C16 124.67(12) . . ? C6 C1 C2 120.04(17) . . ? C6 C1 H1 120.0 . . ? C2 C1 H1 120.0 . . ? C3 C2 C1 120.54(17) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C4 C3 C2 119.68(16) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 120.26(18) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 120.56(16) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C1 118.92(14) . . ? C5 C6 C7 122.00(13) . . ? C1 C6 C7 119.06(13) . . ? N1 C7 C6 111.16(11) . . ? N1 C7 C8 109.75(11) . . ? C6 C7 C8 114.38(11) . . ? N1 C7 H7 107.1 . . ? C6 C7 H7 107.1 . . ? C8 C7 H7 107.1 . . ? C9 C8 C13 118.51(15) . . ? C9 C8 C7 122.51(13) . . ? C13 C8 C7 118.98(14) . . ? C8 C9 C10 120.80(17) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 120.04(19) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 119.91(17) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C13 120.48(18) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C8 C13 C12 120.26(18) . . ? C8 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 N1 106.98(12) . . ? C15 C14 H14 126.5 . . ? N1 C14 H14 126.5 . . ? C14 C15 N2 106.99(12) . . ? C14 C15 H15 126.5 . . ? N2 C15 H15 126.5 . . ? N2 C16 H16A 109.5 . . ? N2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N2 C17 N1 105.39(11) . . ? N2 C17 B1 125.99(12) . . ? N1 C17 B1 128.62(12) . . ? C23 C18 C19 113.59(14) . . ? C23 C18 B1 123.86(13) . . ? C19 C18 B1 122.54(13) . . ? F1 C19 C20 116.28(14) . . ? F1 C19 C18 119.10(13) . . ? C20 C19 C18 124.61(15) . . ? F2 C20 C21 119.99(15) . . ? F2 C20 C19 120.84(16) . . ? C21 C20 C19 119.17(16) . . ? F3 C21 C20 120.17(18) . . ? F3 C21 C22 120.46(17) . . ? C20 C21 C22 119.38(15) . . ? F4 C22 C21 120.34(16) . . ? F4 C22 C23 120.20(17) . . ? C21 C22 C23 119.46(15) . . ? F5 C23 C18 119.98(14) . . ? F5 C23 C22 116.24(14) . . ? C18 C23 C22 123.78(15) . . ? C17 B1 C18 110.25(11) . . ? C17 B1 H1A 107.5(10) . . ? C18 B1 H1A 110.1(10) . . ? C17 B1 H1B 109.8(10) . . ? C18 B1 H1B 109.4(10) . . ? H1A B1 H1B 109.8(13) . . ? 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 C19 1.3569(18) . ? F2 C20 1.347(2) . ? F3 C21 1.3444(19) . ? F4 C22 1.3421(19) . ? F5 C23 1.3542(18) . ? N1 C17 1.3488(17) . ? N1 C14 1.3842(17) . ? N1 C7 1.4821(17) . ? N2 C17 1.3457(17) . ? N2 C15 1.3768(18) . ? N2 C16 1.4621(18) . ? C1 C6 1.383(2) . ? C1 C2 1.388(2) . ? C1 H1 0.9300 . ? C2 C3 1.374(3) . ? C2 H2 0.9300 . ? C3 C4 1.367(3) . ? C3 H3 0.9300 . ? C4 C5 1.387(2) . ? C4 H4 0.9300 . ? C5 C6 1.382(2) . ? C5 H5 0.9300 . ? C6 C7 1.5181(19) . ? C7 C8 1.5233(19) . ? C7 H7 0.9800 . ? C8 C9 1.382(2) . ? C8 C13 1.385(2) . ? C9 C10 1.395(2) . ? C9 H9 0.9300 . ? C10 C11 1.363(3) . ? C10 H10 0.9300 . ? C11 C12 1.372(3) . ? C11 H11 0.9300 . ? C12 C13 1.391(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.337(2) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 B1 1.6133(19) . ? C18 C23 1.380(2) . ? C18 C19 1.388(2) . ? C18 B1 1.630(2) . ? C19 C20 1.374(2) . ? C20 C21 1.368(3) . ? C21 C22 1.370(3) . ? C22 C23 1.389(2) . ? B1 H1A 1.167(19) . ? B1 H1B 1.130(19) . ? 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 -0.1(3) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C5 0.6(3) . . . . ? C3 C4 C5 C6 -0.7(3) . . . . ? C4 C5 C6 C1 0.4(2) . . . . ? C4 C5 C6 C7 -178.40(14) . . . . ? C2 C1 C6 C5 0.0(2) . . . . ? C2 C1 C6 C7 178.82(15) . . . . ? C17 N1 C7 C6 -80.10(15) . . . . ? C14 N1 C7 C6 98.57(15) . . . . ? C17 N1 C7 C8 152.37(12) . . . . ? C14 N1 C7 C8 -28.96(17) . . . . ? C5 C6 C7 N1 -37.55(18) . . . . ? C1 C6 C7 N1 143.69(13) . . . . ? C5 C6 C7 C8 87.42(16) . . . . ? C1 C6 C7 C8 -91.34(16) . . . . ? N1 C7 C8 C9 103.61(16) . . . . ? C6 C7 C8 C9 -22.1(2) . . . . ? N1 C7 C8 C13 -75.95(16) . . . . ? C6 C7 C8 C13 158.34(14) . . . . ? C13 C8 C9 C10 0.2(2) . . . . ? C7 C8 C9 C10 -179.35(15) . . . . ? C8 C9 C10 C11 0.0(3) . . . . ? C9 C10 C11 C12 -0.2(3) . . . . ? C10 C11 C12 C13 0.0(3) . . . . ? C9 C8 C13 C12 -0.3(2) . . . . ? C7 C8 C13 C12 179.23(15) . . . . ? C11 C12 C13 C8 0.2(3) . . . . ? C17 N1 C14 C15 -0.43(15) . . . . ? C7 N1 C14 C15 -179.27(12) . . . . ? N1 C14 C15 N2 0.29(16) . . . . ? C17 N2 C15 C14 -0.06(16) . . . . ? C16 N2 C15 C14 179.13(13) . . . . ? C15 N2 C17 N1 -0.21(15) . . . . ? C16 N2 C17 N1 -179.40(12) . . . . ? C15 N2 C17 B1 -179.99(13) . . . . ? C16 N2 C17 B1 0.8(2) . . . . ? C14 N1 C17 N2 0.39(14) . . . . ? C7 N1 C17 N2 179.24(11) . . . . ? C14 N1 C17 B1 -179.83(13) . . . . ? C7 N1 C17 B1 -1.0(2) . . . . ? C23 C18 C19 F1 -178.15(12) . . . . ? B1 C18 C19 F1 0.9(2) . . . . ? C23 C18 C19 C20 1.2(2) . . . . ? B1 C18 C19 C20 -179.81(14) . . . . ? F1 C19 C20 F2 -0.7(2) . . . . ? C18 C19 C20 F2 179.98(14) . . . . ? F1 C19 C20 C21 178.89(14) . . . . ? C18 C19 C20 C21 -0.5(3) . . . . ? F2 C20 C21 F3 -0.5(2) . . . . ? C19 C20 C21 F3 179.88(15) . . . . ? F2 C20 C21 C22 179.41(15) . . . . ? C19 C20 C21 C22 -0.2(2) . . . . ? F3 C21 C22 F4 -1.0(3) . . . . ? C20 C21 C22 F4 179.05(15) . . . . ? F3 C21 C22 C23 179.91(14) . . . . ? C20 C21 C22 C23 0.0(2) . . . . ? C19 C18 C23 F5 178.71(12) . . . . ? B1 C18 C23 F5 -0.3(2) . . . . ? C19 C18 C23 C22 -1.4(2) . . . . ? B1 C18 C23 C22 179.61(14) . . . . ? F4 C22 C23 F5 1.7(2) . . . . ? C21 C22 C23 F5 -179.20(14) . . . . ? F4 C22 C23 C18 -178.20(14) . . . . ? C21 C22 C23 C18 0.9(2) . . . . ? N2 C17 B1 C18 62.88(18) . . . . ? N1 C17 B1 C18 -116.85(15) . . . . ? C23 C18 B1 C17 -133.66(14) . . . . ? C19 C18 B1 C17 47.43(19) . . . . ?