# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Soji Shimizu' 'Tatsuya Otaki' 'Yoko Yamazaki' 'Nagao Kobayashi' _publ_contact_author_email ssoji@m.tohoku.ac.jp _publ_contact_author_name 'Soji Shimizu' data_test _database_code_depnum_ccdc_archive 'CCDC 861339' #TrackingRef '8940_web_deposit_cif_file_0_SojiShimizu_1325862550.CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H12 B Cl F8 N6' _chemical_formula_sum 'C24 H12 B Cl F8 N6' _chemical_formula_weight 582.66 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn ' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_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' _cell_length_a 11.473(6) _cell_length_b 11.029(6) _cell_length_c 18.450(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.194(6) _cell_angle_gamma 90.00 _cell_volume 2331(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5142 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 27.66 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.660 _exptl_crystal_density_method ? _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.257 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8093 _exptl_absorpt_correction_T_max 0.9748 _exptl_absorpt_process_details ? _exptl_special_details ; SADABS (Sheldrick, 1997) ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayered confocal mirror' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21026 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4098 _reflns_number_gt 3556 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;Yadokari-XG 2009 (Wakita, Nemoto et al., 2009) ; _computing_publication_material ;Yadokari-XG 2009 (Wakita, Nemoto et al., 2009) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0354P)^2^+1.9463P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4098 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0396 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.0838 _refine_ls_wR_factor_gt 0.0795 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.13061(13) 0.25877(14) 0.23455(8) 0.0164(3) Uani 1 1 d . . . C1 C 0.08633(16) 0.32269(17) 0.17651(10) 0.0177(4) Uani 1 1 d . . . C2 C -0.01572(16) 0.38530(17) 0.20099(10) 0.0190(4) Uani 1 1 d . . . C3 C -0.09731(17) 0.46275(18) 0.16674(10) 0.0209(4) Uani 1 1 d . . . C4 C -0.17979(17) 0.51776(18) 0.20665(10) 0.0217(4) Uani 1 1 d . . . C5 C -0.18299(17) 0.49747(18) 0.28156(10) 0.0215(4) Uani 1 1 d . . . C6 C -0.10316(16) 0.42125(17) 0.31664(10) 0.0193(4) Uani 1 1 d . . . C7 C -0.01894(16) 0.36423(17) 0.27737(10) 0.0184(4) Uani 1 1 d . . . C8 C 0.08143(16) 0.29048(17) 0.29909(10) 0.0173(4) Uani 1 1 d . . . N2 N 0.14028(13) 0.28092(14) 0.36348(8) 0.0174(3) Uani 1 1 d . . . N3 N 0.30733(13) 0.21442(14) 0.30187(8) 0.0165(3) Uani 1 1 d . . . C9 C 0.25363(17) 0.25007(16) 0.36393(9) 0.0169(4) Uani 1 1 d . . . C10 C 0.34879(17) 0.27762(16) 0.41602(10) 0.0177(4) Uani 1 1 d . . . C11 C 0.35270(17) 0.31745(17) 0.48764(10) 0.0200(4) Uani 1 1 d . . . C12 C 0.45765(18) 0.35099(17) 0.52095(10) 0.0207(4) Uani 1 1 d . . . C13 C 0.56047(17) 0.34977(17) 0.48330(10) 0.0201(4) Uani 1 1 d . . . C14 C 0.55954(16) 0.31042(17) 0.41277(10) 0.0192(4) Uani 1 1 d . . . C15 C 0.45487(17) 0.27126(17) 0.37854(10) 0.0180(4) Uani 1 1 d . . . C16 C 0.42364(16) 0.23518(17) 0.30497(10) 0.0177(4) Uani 1 1 d . . . N4 N 0.48732(14) 0.24315(14) 0.24407(8) 0.0185(3) Uani 1 1 d . . . N5 N 0.30761(13) 0.24222(14) 0.17458(8) 0.0167(3) Uani 1 1 d . . . C17 C 0.42659(16) 0.25260(16) 0.18144(10) 0.0176(4) Uani 1 1 d . . . C18 C 0.46779(17) 0.28680(17) 0.10721(9) 0.0195(4) Uani 1 1 d . . . C19 C 0.35455(16) 0.35527(17) 0.07298(9) 0.0184(4) Uani 1 1 d . . . C20 C 0.25730(17) 0.30665(16) 0.11879(9) 0.0173(4) Uani 1 1 d . . . N6 N 0.14568(14) 0.33999(14) 0.11540(8) 0.0184(3) Uani 1 1 d . . . B1 B 0.23900(19) 0.18688(19) 0.23268(11) 0.0170(4) Uani 1 1 d . . . Cl1 Cl 0.21475(4) 0.02074(4) 0.21683(2) 0.02240(12) Uani 1 1 d . . . F1 F -0.09618(10) 0.48484(11) 0.09381(6) 0.0291(3) Uani 1 1 d . . . F2 F -0.25985(10) 0.59290(11) 0.17521(6) 0.0273(3) Uani 1 1 d . . . F3 F -0.26500(10) 0.55440(11) 0.31824(6) 0.0286(3) Uani 1 1 d . . . F4 F -0.10725(10) 0.40380(10) 0.38887(5) 0.0225(3) Uani 1 1 d . . . F5 F 0.25477(10) 0.32409(11) 0.52487(6) 0.0257(3) Uani 1 1 d . . . F6 F 0.46345(10) 0.38898(11) 0.59048(6) 0.0266(3) Uani 1 1 d . . . F7 F 0.65978(10) 0.39123(10) 0.51725(6) 0.0254(3) Uani 1 1 d . . . F8 F 0.65859(9) 0.31205(11) 0.37690(6) 0.0242(3) Uani 1 1 d . . . C21 C 0.48998(18) 0.16709(19) 0.06675(10) 0.0246(4) Uani 1 1 d . . . H1 H 0.5541 0.1229 0.0922 0.037 Uiso 1 1 calc R . . H2 H 0.5108 0.1852 0.0171 0.037 Uiso 1 1 calc R . . H3 H 0.4191 0.1173 0.0653 0.037 Uiso 1 1 calc R . . C22 C 0.57973(17) 0.3618(2) 0.11263(11) 0.0250(4) Uani 1 1 d . . . H4 H 0.5672 0.4350 0.1413 0.037 Uiso 1 1 calc R . . H5 H 0.6011 0.3849 0.0638 0.037 Uiso 1 1 calc R . . H6 H 0.6428 0.3137 0.1363 0.037 Uiso 1 1 calc R . . C23 C 0.32982(18) 0.33536(18) -0.00833(10) 0.0217(4) Uani 1 1 d . . . H7 H 0.3213 0.2484 -0.0181 0.033 Uiso 1 1 calc R . . H8 H 0.3947 0.3676 -0.0348 0.033 Uiso 1 1 calc R . . H9 H 0.2576 0.3773 -0.0242 0.033 Uiso 1 1 calc R . . C24 C 0.35934(18) 0.49229(18) 0.08803(10) 0.0232(4) Uani 1 1 d . . . H10 H 0.2839 0.5289 0.0733 0.035 Uiso 1 1 calc R . . H11 H 0.4207 0.5292 0.0604 0.035 Uiso 1 1 calc R . . H12 H 0.3765 0.5062 0.1400 0.035 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0139(8) 0.0185(8) 0.0169(7) 0.0004(6) 0.0007(6) -0.0013(6) C1 0.0172(10) 0.0187(9) 0.0171(9) -0.0011(7) -0.0013(7) -0.0025(8) C2 0.0153(10) 0.0225(10) 0.0192(9) -0.0009(7) 0.0000(7) -0.0033(8) C3 0.0204(10) 0.0267(10) 0.0153(9) 0.0015(8) -0.0017(7) -0.0031(8) C4 0.0151(10) 0.0223(10) 0.0273(10) 0.0027(8) -0.0042(8) 0.0007(8) C5 0.0153(10) 0.0228(10) 0.0269(10) -0.0027(8) 0.0046(8) -0.0008(8) C6 0.0170(10) 0.0221(10) 0.0188(9) -0.0004(7) 0.0020(7) -0.0041(8) C7 0.0147(10) 0.0212(10) 0.0191(9) 0.0002(7) 0.0000(7) -0.0044(8) C8 0.0151(10) 0.0185(9) 0.0184(9) 0.0004(7) 0.0033(7) -0.0030(8) N2 0.0172(9) 0.0180(8) 0.0172(8) 0.0032(6) 0.0018(6) -0.0027(6) N3 0.0165(8) 0.0177(8) 0.0154(7) 0.0021(6) 0.0006(6) 0.0011(6) C9 0.0192(10) 0.0167(9) 0.0151(9) 0.0023(7) 0.0036(7) -0.0009(8) C10 0.0191(10) 0.0169(9) 0.0172(9) 0.0043(7) 0.0006(7) 0.0013(8) C11 0.0187(10) 0.0224(10) 0.0191(9) 0.0035(7) 0.0032(8) 0.0027(8) C12 0.0266(11) 0.0212(10) 0.0141(9) 0.0001(7) -0.0013(8) 0.0049(8) C13 0.0170(10) 0.0201(9) 0.0226(10) 0.0017(8) -0.0057(8) 0.0021(8) C14 0.0154(10) 0.0210(10) 0.0212(9) 0.0043(7) 0.0014(7) 0.0035(8) C15 0.0188(10) 0.0180(9) 0.0172(9) 0.0035(7) 0.0004(7) 0.0026(8) C16 0.0170(10) 0.0174(9) 0.0187(9) 0.0032(7) 0.0019(7) 0.0022(8) N4 0.0178(8) 0.0217(8) 0.0162(8) 0.0008(6) 0.0020(6) 0.0025(7) N5 0.0170(9) 0.0176(8) 0.0153(7) -0.0006(6) 0.0009(6) 0.0010(6) C17 0.0176(10) 0.0159(9) 0.0193(9) -0.0003(7) 0.0021(7) 0.0022(8) C18 0.0193(10) 0.0239(10) 0.0154(9) 0.0019(7) 0.0017(7) 0.0002(8) C19 0.0171(10) 0.0221(10) 0.0159(9) 0.0004(7) 0.0017(7) -0.0005(8) C20 0.0214(10) 0.0182(9) 0.0123(8) -0.0028(7) -0.0003(7) -0.0008(8) N6 0.0185(9) 0.0216(8) 0.0150(7) -0.0015(6) -0.0012(6) -0.0006(7) B1 0.0181(11) 0.0163(10) 0.0163(10) -0.0001(8) 0.0004(8) -0.0023(8) Cl1 0.0276(3) 0.0180(2) 0.0218(2) -0.00107(18) 0.00237(18) -0.0015(2) F1 0.0222(6) 0.0348(7) 0.0296(6) 0.0053(5) -0.0053(5) 0.0064(5) F2 0.0211(6) 0.0311(6) 0.0293(6) 0.0044(5) -0.0028(5) 0.0069(5) F3 0.0248(7) 0.0336(7) 0.0280(6) -0.0001(5) 0.0075(5) 0.0076(5) F4 0.0210(6) 0.0291(6) 0.0179(5) 0.0025(4) 0.0049(4) 0.0007(5) F5 0.0188(6) 0.0398(7) 0.0189(5) -0.0022(5) 0.0056(4) -0.0010(5) F6 0.0273(7) 0.0345(7) 0.0176(5) -0.0049(5) -0.0016(5) 0.0026(5) F7 0.0194(6) 0.0303(6) 0.0257(6) -0.0028(5) -0.0057(5) 0.0004(5) F8 0.0145(6) 0.0348(7) 0.0232(6) 0.0010(5) 0.0008(4) 0.0009(5) C21 0.0228(11) 0.0286(11) 0.0225(10) 0.0003(8) 0.0038(8) 0.0063(9) C22 0.0190(11) 0.0333(12) 0.0228(10) 0.0039(8) 0.0019(8) -0.0026(9) C23 0.0229(11) 0.0262(10) 0.0161(9) 0.0008(8) 0.0017(8) -0.0011(8) C24 0.0274(11) 0.0216(10) 0.0209(9) 0.0003(8) 0.0030(8) -0.0012(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 N1 C1 1.357(2) . ? N1 C8 1.391(2) . ? N1 B1 1.477(3) . ? C1 N6 1.363(2) . ? C1 C2 1.453(3) . ? C2 C3 1.393(3) . ? C2 C7 1.431(3) . ? C3 F1 1.368(2) . ? C3 C4 1.372(3) . ? C4 F2 1.345(2) . ? C4 C5 1.403(3) . ? C5 F3 1.345(2) . ? C5 C6 1.378(3) . ? C6 F4 1.350(2) . ? C6 C7 1.390(3) . ? C7 C8 1.448(3) . ? C8 N2 1.337(2) . ? N2 C9 1.344(3) . ? N3 C16 1.352(3) . ? N3 C9 1.387(2) . ? N3 B1 1.492(3) . ? C9 C10 1.446(3) . ? C10 C11 1.391(3) . ? C10 C15 1.435(3) . ? C11 F5 1.351(2) . ? C11 C12 1.372(3) . ? C12 F6 1.348(2) . ? C12 C13 1.402(3) . ? C13 F7 1.349(2) . ? C13 C14 1.371(3) . ? C14 F8 1.347(2) . ? C14 C15 1.394(3) . ? C15 C16 1.440(3) . ? C16 N4 1.377(2) . ? N4 C17 1.320(2) . ? N5 C20 1.353(2) . ? N5 C17 1.369(3) . ? N5 B1 1.495(3) . ? C17 C18 1.521(3) . ? C18 C22 1.526(3) . ? C18 C21 1.545(3) . ? C18 C19 1.602(3) . ? C19 C23 1.527(3) . ? C19 C20 1.534(3) . ? C19 C24 1.537(3) . ? C20 N6 1.331(3) . ? B1 Cl1 1.874(2) . ? C21 H1 0.9800 . ? C21 H2 0.9800 . ? C21 H3 0.9800 . ? C22 H4 0.9800 . ? C22 H5 0.9800 . ? C22 H6 0.9800 . ? C23 H7 0.9800 . ? C23 H8 0.9800 . ? C23 H9 0.9800 . ? C24 H10 0.9800 . ? C24 H11 0.9800 . ? C24 H12 0.9800 . ? 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 C1 N1 C8 113.16(16) . . ? C1 N1 B1 122.63(15) . . ? C8 N1 B1 122.50(15) . . ? N1 C1 N6 122.91(17) . . ? N1 C1 C2 105.92(16) . . ? N6 C1 C2 129.74(17) . . ? C3 C2 C7 119.54(17) . . ? C3 C2 C1 133.11(17) . . ? C7 C2 C1 107.13(16) . . ? F1 C3 C4 119.58(17) . . ? F1 C3 C2 120.83(17) . . ? C4 C3 C2 119.59(17) . . ? F2 C4 C3 121.05(17) . . ? F2 C4 C5 117.95(17) . . ? C3 C4 C5 120.99(18) . . ? F3 C5 C6 120.92(17) . . ? F3 C5 C4 118.61(17) . . ? C6 C5 C4 120.46(18) . . ? F4 C6 C5 119.47(17) . . ? F4 C6 C7 120.90(17) . . ? C5 C6 C7 119.63(17) . . ? C6 C7 C2 119.79(17) . . ? C6 C7 C8 132.46(17) . . ? C2 C7 C8 107.46(16) . . ? N2 C8 N1 122.14(17) . . ? N2 C8 C7 130.12(17) . . ? N1 C8 C7 104.99(15) . . ? C8 N2 C9 117.77(16) . . ? C16 N3 C9 113.56(15) . . ? C16 N3 B1 122.76(16) . . ? C9 N3 B1 121.85(16) . . ? N2 C9 N3 122.75(16) . . ? N2 C9 C10 130.20(17) . . ? N3 C9 C10 104.75(16) . . ? C11 C10 C15 119.34(17) . . ? C11 C10 C9 132.92(18) . . ? C15 C10 C9 107.38(16) . . ? F5 C11 C12 119.45(17) . . ? F5 C11 C10 121.09(17) . . ? C12 C11 C10 119.46(18) . . ? F6 C12 C11 120.38(17) . . ? F6 C12 C13 118.45(17) . . ? C11 C12 C13 121.14(17) . . ? F7 C13 C14 120.64(17) . . ? F7 C13 C12 118.61(16) . . ? C14 C13 C12 120.73(17) . . ? F8 C14 C13 119.99(17) . . ? F8 C14 C15 120.72(17) . . ? C13 C14 C15 119.27(18) . . ? C14 C15 C10 119.94(17) . . ? C14 C15 C16 132.48(17) . . ? C10 C15 C16 107.13(16) . . ? N3 C16 N4 122.93(16) . . ? N3 C16 C15 106.25(15) . . ? N4 C16 C15 129.49(17) . . ? C17 N4 C16 116.19(17) . . ? C20 N5 C17 114.04(16) . . ? C20 N5 B1 122.71(16) . . ? C17 N5 B1 122.01(15) . . ? N4 C17 N5 123.33(17) . . ? N4 C17 C18 129.24(17) . . ? N5 C17 C18 107.21(15) . . ? C17 C18 C22 112.21(15) . . ? C17 C18 C21 106.92(15) . . ? C22 C18 C21 109.53(16) . . ? C17 C18 C19 100.72(15) . . ? C22 C18 C19 115.55(16) . . ? C21 C18 C19 111.36(15) . . ? C23 C19 C20 112.96(15) . . ? C23 C19 C24 108.77(15) . . ? C20 C19 C24 105.30(15) . . ? C23 C19 C18 114.95(15) . . ? C20 C19 C18 102.53(14) . . ? C24 C19 C18 111.85(16) . . ? N6 C20 N5 123.33(17) . . ? N6 C20 C19 127.25(16) . . ? N5 C20 C19 108.07(16) . . ? C20 N6 C1 116.52(16) . . ? N1 B1 N3 105.90(15) . . ? N1 B1 N5 105.98(15) . . ? N3 B1 N5 104.95(16) . . ? N1 B1 Cl1 114.25(14) . . ? N3 B1 Cl1 113.51(13) . . ? N5 B1 Cl1 111.52(13) . . ? C18 C21 H1 109.5 . . ? C18 C21 H2 109.5 . . ? H1 C21 H2 109.5 . . ? C18 C21 H3 109.5 . . ? H1 C21 H3 109.5 . . ? H2 C21 H3 109.5 . . ? C18 C22 H4 109.5 . . ? C18 C22 H5 109.5 . . ? H4 C22 H5 109.5 . . ? C18 C22 H6 109.5 . . ? H4 C22 H6 109.5 . . ? H5 C22 H6 109.5 . . ? C19 C23 H7 109.5 . . ? C19 C23 H8 109.5 . . ? H7 C23 H8 109.5 . . ? C19 C23 H9 109.5 . . ? H7 C23 H9 109.5 . . ? H8 C23 H9 109.5 . . ? C19 C24 H10 109.5 . . ? C19 C24 H11 109.5 . . ? H10 C24 H11 109.5 . . ? C19 C24 H12 109.5 . . ? H10 C24 H12 109.5 . . ? H11 C24 H12 109.5 . . ? 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 C8 N1 C1 N6 155.98(17) . . . . ? B1 N1 C1 N6 -9.5(3) . . . . ? C8 N1 C1 C2 -11.6(2) . . . . ? B1 N1 C1 C2 -177.01(16) . . . . ? N1 C1 C2 C3 -179.3(2) . . . . ? N6 C1 C2 C3 14.3(4) . . . . ? N1 C1 C2 C7 6.3(2) . . . . ? N6 C1 C2 C7 -160.08(18) . . . . ? C7 C2 C3 F1 179.84(16) . . . . ? C1 C2 C3 F1 6.0(3) . . . . ? C7 C2 C3 C4 -0.1(3) . . . . ? C1 C2 C3 C4 -173.9(2) . . . . ? F1 C3 C4 F2 0.2(3) . . . . ? C2 C3 C4 F2 -179.93(17) . . . . ? F1 C3 C4 C5 -179.70(17) . . . . ? C2 C3 C4 C5 0.2(3) . . . . ? F2 C4 C5 F3 -0.4(3) . . . . ? C3 C4 C5 F3 179.46(17) . . . . ? F2 C4 C5 C6 179.93(17) . . . . ? C3 C4 C5 C6 -0.2(3) . . . . ? F3 C5 C6 F4 -0.2(3) . . . . ? C4 C5 C6 F4 179.46(17) . . . . ? F3 C5 C6 C7 -179.60(17) . . . . ? C4 C5 C6 C7 0.0(3) . . . . ? F4 C6 C7 C2 -179.31(16) . . . . ? C5 C6 C7 C2 0.1(3) . . . . ? F4 C6 C7 C8 -6.4(3) . . . . ? C5 C6 C7 C8 173.03(19) . . . . ? C3 C2 C7 C6 -0.1(3) . . . . ? C1 C2 C7 C6 175.20(17) . . . . ? C3 C2 C7 C8 -174.63(17) . . . . ? C1 C2 C7 C8 0.7(2) . . . . ? C1 N1 C8 N2 -151.01(17) . . . . ? B1 N1 C8 N2 14.4(3) . . . . ? C1 N1 C8 C7 11.9(2) . . . . ? B1 N1 C8 C7 177.39(16) . . . . ? C6 C7 C8 N2 -19.7(3) . . . . ? C2 C7 C8 N2 153.85(19) . . . . ? C6 C7 C8 N1 179.25(19) . . . . ? C2 C7 C8 N1 -7.2(2) . . . . ? N1 C8 N2 C9 6.1(3) . . . . ? C7 C8 N2 C9 -152.12(19) . . . . ? C8 N2 C9 N3 -7.8(3) . . . . ? C8 N2 C9 C10 152.26(19) . . . . ? C16 N3 C9 N2 154.13(17) . . . . ? B1 N3 C9 N2 -10.9(3) . . . . ? C16 N3 C9 C10 -10.2(2) . . . . ? B1 N3 C9 C10 -175.24(16) . . . . ? N2 C9 C10 C11 17.4(3) . . . . ? N3 C9 C10 C11 -179.9(2) . . . . ? N2 C9 C10 C15 -155.50(19) . . . . ? N3 C9 C10 C15 7.21(19) . . . . ? C15 C10 C11 F5 -179.65(16) . . . . ? C9 C10 C11 F5 8.1(3) . . . . ? C15 C10 C11 C12 0.6(3) . . . . ? C9 C10 C11 C12 -171.64(19) . . . . ? F5 C11 C12 F6 0.7(3) . . . . ? C10 C11 C12 F6 -179.51(16) . . . . ? F5 C11 C12 C13 -177.54(17) . . . . ? C10 C11 C12 C13 2.2(3) . . . . ? F6 C12 C13 F7 -2.6(3) . . . . ? C11 C12 C13 F7 175.68(17) . . . . ? F6 C12 C13 C14 179.14(17) . . . . ? C11 C12 C13 C14 -2.5(3) . . . . ? F7 C13 C14 F8 0.5(3) . . . . ? C12 C13 C14 F8 178.70(16) . . . . ? F7 C13 C14 C15 -178.23(16) . . . . ? C12 C13 C14 C15 0.0(3) . . . . ? F8 C14 C15 C10 -175.91(16) . . . . ? C13 C14 C15 C10 2.8(3) . . . . ? F8 C14 C15 C16 -4.7(3) . . . . ? C13 C14 C15 C16 174.01(19) . . . . ? C11 C10 C15 C14 -3.1(3) . . . . ? C9 C10 C15 C14 170.92(16) . . . . ? C11 C10 C15 C16 -176.34(16) . . . . ? C9 C10 C15 C16 -2.3(2) . . . . ? C9 N3 C16 N4 -159.08(17) . . . . ? B1 N3 C16 N4 5.8(3) . . . . ? C9 N3 C16 C15 8.9(2) . . . . ? B1 N3 C16 C15 173.76(16) . . . . ? C14 C15 C16 N3 -175.71(19) . . . . ? C10 C15 C16 N3 -3.7(2) . . . . ? C14 C15 C16 N4 -8.8(3) . . . . ? C10 C15 C16 N4 163.19(18) . . . . ? N3 C16 N4 C17 12.5(3) . . . . ? C15 C16 N4 C17 -152.46(19) . . . . ? C16 N4 C17 N5 -6.9(3) . . . . ? C16 N4 C17 C18 167.00(18) . . . . ? C20 N5 C17 N4 150.73(18) . . . . ? B1 N5 C17 N4 -16.9(3) . . . . ? C20 N5 C17 C18 -24.3(2) . . . . ? B1 N5 C17 C18 168.05(16) . . . . ? N4 C17 C18 C22 -24.0(3) . . . . ? N5 C17 C18 C22 150.64(16) . . . . ? N4 C17 C18 C21 96.1(2) . . . . ? N5 C17 C18 C21 -89.25(18) . . . . ? N4 C17 C18 C19 -147.51(19) . . . . ? N5 C17 C18 C19 27.18(18) . . . . ? C17 C18 C19 C23 -143.97(16) . . . . ? C22 C18 C19 C23 94.9(2) . . . . ? C21 C18 C19 C23 -30.9(2) . . . . ? C17 C18 C19 C20 -21.00(17) . . . . ? C22 C18 C19 C20 -142.12(16) . . . . ? C21 C18 C19 C20 92.09(17) . . . . ? C17 C18 C19 C24 91.36(17) . . . . ? C22 C18 C19 C24 -29.8(2) . . . . ? C21 C18 C19 C24 -155.55(16) . . . . ? C17 N5 C20 N6 -158.47(17) . . . . ? B1 N5 C20 N6 9.0(3) . . . . ? C17 N5 C20 C19 9.2(2) . . . . ? B1 N5 C20 C19 176.66(16) . . . . ? C23 C19 C20 N6 -59.8(2) . . . . ? C24 C19 C20 N6 58.7(2) . . . . ? C18 C19 C20 N6 175.88(17) . . . . ? C23 C19 C20 N5 133.16(16) . . . . ? C24 C19 C20 N5 -108.27(17) . . . . ? C18 C19 C20 N5 8.86(18) . . . . ? N5 C20 N6 C1 9.9(3) . . . . ? C19 C20 N6 C1 -155.32(17) . . . . ? N1 C1 N6 C20 -9.8(3) . . . . ? C2 C1 N6 C20 154.60(19) . . . . ? C1 N1 B1 N3 135.51(17) . . . . ? C8 N1 B1 N3 -28.6(2) . . . . ? C1 N1 B1 N5 24.4(2) . . . . ? C8 N1 B1 N5 -139.71(16) . . . . ? C1 N1 B1 Cl1 -98.81(18) . . . . ? C8 N1 B1 Cl1 97.10(18) . . . . ? C16 N3 B1 N1 -136.87(17) . . . . ? C9 N3 B1 N1 26.8(2) . . . . ? C16 N3 B1 N5 -25.0(2) . . . . ? C9 N3 B1 N5 138.63(17) . . . . ? C16 N3 B1 Cl1 97.00(18) . . . . ? C9 N3 B1 Cl1 -99.35(18) . . . . ? C20 N5 B1 N1 -24.4(2) . . . . ? C17 N5 B1 N1 142.17(16) . . . . ? C20 N5 B1 N3 -136.15(17) . . . . ? C17 N5 B1 N3 30.4(2) . . . . ? C20 N5 B1 Cl1 100.54(18) . . . . ? C17 N5 B1 Cl1 -92.94(18) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.526 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.049