data_mht13pt1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H18 B F2 N3 O2' _chemical_formula_weight 369.17 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_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' _cell_length_a 30.367(3) _cell_length_b 11.8122(9) _cell_length_c 19.5189(16) _cell_angle_alpha 90.00 _cell_angle_beta 96.413(2) _cell_angle_gamma 90.00 _cell_volume 6957.6(10) _cell_formula_units_Z 16 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1728 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 32.0 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.393 _exptl_crystal_size_mid 0.210 _exptl_crystal_size_min 0.152 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3072 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.975 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details ; SADABS (Sheldrick, 1996) ; _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'APEXII-FR591' _diffrn_measurement_method \w+\f _diffrn_reflns_number 72547 _diffrn_reflns_av_R_equivalents 0.0461 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 43 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 30.53 _reflns_number_total 10615 _reflns_number_gt 8880 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-AXS,2012)' _computing_cell_refinement 'SAINT (Bruker-AXS,2012)' _computing_data_reduction 'SAINT and XPREP (Bruker-AXS,2012)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; xtal 3.6 (Hall,du Boulay, D.J. & Olthof-Hazekamp, R. 1999) ORTEPII (Johnson,C.K., 1976). WinGX (Farrugia, 1999) shelXle (Hübschle,C.B., et al., 2011) ; _computing_publication_material ? _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^)+(0.07P)^2^+0.8P] 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 10615 _refine_ls_number_parameters 495 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1487 _refine_ls_wR_factor_gt 0.1284 _refine_ls_goodness_of_fit_ref 1.464 _refine_ls_restrained_S_all 1.464 _refine_ls_shift/su_max 0.004 _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 F1_1 F 0.33645(2) 0.70399(6) 0.40009(4) 0.02473(15) Uani 1 1 d . . . F2_1 F 0.30017(2) 0.66451(6) 0.49291(4) 0.02822(17) Uani 1 1 d . . . O1_1 O 0.16400(4) 1.40286(8) 0.26526(6) 0.0408(3) Uani 1 1 d . . . O2_1 O 0.11368(3) 1.35206(9) 0.32971(6) 0.0393(2) Uani 1 1 d . . . N1_1 N 0.31032(3) 0.86127(8) 0.46310(5) 0.01878(18) Uani 1 1 d . . . N2_1 N 0.25797(3) 0.73747(8) 0.39005(5) 0.01765(17) Uani 1 1 d . . . N3_1 N 0.14872(4) 1.33656(9) 0.30518(6) 0.0285(2) Uani 1 1 d . . . C1_1 C 0.34285(4) 0.89818(10) 0.51086(6) 0.0231(2) Uani 1 1 d . . . C2_1 C 0.34104(4) 1.01696(10) 0.51439(6) 0.0252(2) Uani 1 1 d . . . H2_1 H 0.3603 1.0635 0.5439 0.030 Uiso 1 1 calc R . . C3_1 C 0.30646(4) 1.05496(10) 0.46763(6) 0.0216(2) Uani 1 1 d . . . C4_1 C 0.28663(3) 0.95578(9) 0.43535(5) 0.0180(2) Uani 1 1 d . . . C5_1 C 0.24942(3) 0.94118(9) 0.38728(5) 0.01617(19) Uani 1 1 d . . . C6_1 C 0.23502(3) 0.83371(9) 0.36444(5) 0.01658(19) Uani 1 1 d . . . C7_1 C 0.19784(3) 0.79753(9) 0.31817(5) 0.0190(2) Uani 1 1 d . . . C8_1 C 0.19928(4) 0.67991(9) 0.31822(6) 0.0217(2) Uani 1 1 d . . . H8_1 H 0.1786 0.6313 0.2927 0.026 Uiso 1 1 calc R . . C9_1 C 0.23658(4) 0.64523(9) 0.36246(6) 0.0204(2) Uani 1 1 d . . . C10_1 C 0.22264(3) 1.04265(9) 0.36338(5) 0.01712(19) Uani 1 1 d . . . C11_1 C 0.23556(4) 1.11188(10) 0.31153(6) 0.0234(2) Uani 1 1 d . . . H11_1 H 0.2610 1.0931 0.2896 0.028 Uiso 1 1 calc R . . C12_1 C 0.21119(4) 1.20880(10) 0.29169(6) 0.0255(2) Uani 1 1 d . . . H12_1 H 0.2196 1.2567 0.2563 0.031 Uiso 1 1 calc R . . C13_1 C 0.17436(4) 1.23340(9) 0.32493(6) 0.0215(2) Uani 1 1 d . . . C14_1 C 0.16023(4) 1.16496(9) 0.37575(6) 0.0215(2) Uani 1 1 d . . . H14_1 H 0.1344 1.1833 0.3969 0.026 Uiso 1 1 calc R . . C15_1 C 0.18494(4) 1.06852(9) 0.39503(6) 0.0197(2) Uani 1 1 d . . . H15_1 H 0.1761 1.0202 0.4299 0.024 Uiso 1 1 calc R . . C16_1 C 0.37517(4) 0.82167(12) 0.55112(7) 0.0299(3) Uani 1 1 d . . . H16A_1 H 0.3916 0.8643 0.5888 0.045 Uiso 1 1 calc R . . H16B_1 H 0.3959 0.7913 0.5208 0.045 Uiso 1 1 calc R . . H16C_1 H 0.3592 0.7591 0.5703 0.045 Uiso 1 1 calc R . . C17_1 C 0.29470(4) 1.17678(10) 0.45465(7) 0.0297(3) Uani 1 1 d . . . H17A_1 H 0.2629 1.1874 0.4570 0.045 Uiso 1 1 calc R . . H17B_1 H 0.3020 1.1986 0.4088 0.045 Uiso 1 1 calc R . . H17C_1 H 0.3115 1.2240 0.4897 0.045 Uiso 1 1 calc R . . C18_1 C 0.16308(4) 0.86668(10) 0.27679(7) 0.0263(2) Uani 1 1 d . . . H18A_1 H 0.1426 0.8979 0.3074 0.040 Uiso 1 1 calc R . . H18B_1 H 0.1466 0.8187 0.2418 0.040 Uiso 1 1 calc R . . H18C_1 H 0.1772 0.9287 0.2541 0.040 Uiso 1 1 calc R . . C19_1 C 0.25251(4) 0.52724(10) 0.37723(7) 0.0284(3) Uani 1 1 d . . . H19A_1 H 0.2493 0.5083 0.4253 0.043 Uiso 1 1 calc R . . H19B_1 H 0.2838 0.5215 0.3695 0.043 Uiso 1 1 calc R . . H19C_1 H 0.2349 0.4745 0.3466 0.043 Uiso 1 1 calc R . . B1_1 B 0.30217(4) 0.73774(10) 0.43783(6) 0.0188(2) Uani 1 1 d . . . F1_2 F -0.09076(2) -0.05923(6) 0.10088(4) 0.02408(15) Uani 1 1 d . . . F2_2 F -0.05036(2) -0.11194(6) 0.01498(4) 0.02625(16) Uani 1 1 d . . . O1_2 O 0.08612(4) 0.63382(8) 0.23043(6) 0.0392(2) Uani 1 1 d . . . O2_2 O 0.13503(3) 0.58683(8) 0.16301(5) 0.0295(2) Uani 1 1 d . . . N1_2 N -0.06127(3) 0.08743(7) 0.03328(5) 0.01679(17) Uani 1 1 d . . . N2_2 N -0.01211(3) -0.02616(7) 0.11703(5) 0.01797(18) Uani 1 1 d . . . N3_2 N 0.10043(3) 0.57039(8) 0.18827(5) 0.0226(2) Uani 1 1 d . . . C1_2 C -0.09113(4) 0.11595(9) -0.02038(6) 0.0204(2) Uani 1 1 d . . . C2_2 C -0.08712(4) 0.23206(10) -0.03394(6) 0.0243(2) Uani 1 1 d . . . H2_2 H -0.1045 0.2734 -0.0689 0.029 Uiso 1 1 calc R . . C3_2 C -0.05349(4) 0.27601(9) 0.01229(6) 0.0213(2) Uani 1 1 d . . . C4_2 C -0.03699(3) 0.18426(8) 0.05534(5) 0.01663(19) Uani 1 1 d . . . C5_2 C -0.00170(3) 0.17633(8) 0.10778(5) 0.01502(18) Uani 1 1 d . . . C6_2 C 0.01061(3) 0.07299(8) 0.13899(5) 0.01653(19) Uani 1 1 d . . . C7_2 C 0.04471(4) 0.04242(9) 0.19259(6) 0.0204(2) Uani 1 1 d . . . C8_2 C 0.04216(4) -0.07390(10) 0.19951(7) 0.0247(2) Uani 1 1 d . . . H8_2 H 0.0611 -0.1191 0.2305 0.030 Uiso 1 1 calc R . . C9_2 C 0.00685(4) -0.11398(9) 0.15296(6) 0.0222(2) Uani 1 1 d . . . C10_2 C 0.02470(3) 0.27964(8) 0.12835(5) 0.01555(19) Uani 1 1 d . . . C11_2 C 0.00639(4) 0.36655(9) 0.16434(6) 0.0193(2) Uani 1 1 d . . . H11_2 H -0.0231 0.3604 0.1756 0.023 Uiso 1 1 calc R . . C12_2 C 0.03134(4) 0.46209(9) 0.18369(6) 0.0214(2) Uani 1 1 d . . . H12_2 H 0.0191 0.5217 0.2083 0.026 Uiso 1 1 calc R . . C13_2 C 0.07417(3) 0.46916(8) 0.16669(5) 0.01723(19) Uani 1 1 d . . . C14_2 C 0.09322(3) 0.38509(9) 0.13036(6) 0.0186(2) Uani 1 1 d . . . H14_2 H 0.1227 0.3923 0.1189 0.022 Uiso 1 1 calc R . . C15_2 C 0.06793(3) 0.28963(9) 0.11113(5) 0.0181(2) Uani 1 1 d . . . H15_2 H 0.0802 0.2308 0.0861 0.022 Uiso 1 1 calc R . . C16_2 C -0.12196(4) 0.03390(10) -0.05850(6) 0.0272(2) Uani 1 1 d . . . H16A_2 H -0.1466 0.0750 -0.0841 0.041 Uiso 1 1 calc R . . H16B_2 H -0.1336 -0.0180 -0.0257 0.041 Uiso 1 1 calc R . . H16C_2 H -0.1060 -0.0094 -0.0908 0.041 Uiso 1 1 calc R . . C17_2 C -0.03811(5) 0.39628(11) 0.01185(7) 0.0331(3) Uani 1 1 d . . . H17A_2 H -0.0058 0.3981 0.0131 0.050 Uiso 1 1 calc R . . H17B_2 H -0.0470 0.4357 0.0523 0.050 Uiso 1 1 calc R . . H17C_2 H -0.0515 0.4338 -0.0302 0.050 Uiso 1 1 calc R . . C18_2 C 0.07701(4) 0.11585(11) 0.23603(7) 0.0278(3) Uani 1 1 d . . . H18A_2 H 0.1019 0.1345 0.2102 0.042 Uiso 1 1 calc R . . H18B_2 H 0.0880 0.0753 0.2783 0.042 Uiso 1 1 calc R . . H18C_2 H 0.0622 0.1857 0.2479 0.042 Uiso 1 1 calc R . . C19_2 C -0.00955(5) -0.23265(10) 0.14412(8) 0.0317(3) Uani 1 1 d . . . H19A_2 H -0.0088 -0.2561 0.0961 0.048 Uiso 1 1 calc R . . H19B_2 H -0.0400 -0.2369 0.1560 0.048 Uiso 1 1 calc R . . H19C_2 H 0.0094 -0.2829 0.1745 0.048 Uiso 1 1 calc R . . B1_2 B -0.05456(4) -0.03124(10) 0.06560(6) 0.0169(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1_1 0.0160(3) 0.0246(3) 0.0343(4) -0.0011(3) 0.0060(3) 0.0030(2) F2_1 0.0305(4) 0.0284(4) 0.0251(4) 0.0108(3) 0.0004(3) -0.0003(3) O1_1 0.0469(6) 0.0243(5) 0.0473(6) 0.0120(4) -0.0119(5) 0.0000(4) O2_1 0.0329(5) 0.0332(5) 0.0492(6) -0.0041(4) -0.0068(4) 0.0144(4) N1_1 0.0147(4) 0.0222(4) 0.0189(4) 0.0005(3) -0.0004(3) 0.0017(3) N2_1 0.0150(4) 0.0174(4) 0.0205(4) 0.0007(3) 0.0019(3) 0.0014(3) N3_1 0.0307(5) 0.0196(5) 0.0315(5) -0.0014(4) -0.0134(4) 0.0019(4) C1_1 0.0171(5) 0.0322(6) 0.0197(5) -0.0026(4) -0.0001(4) 0.0020(4) C2_1 0.0184(5) 0.0310(6) 0.0253(5) -0.0085(4) -0.0017(4) -0.0003(4) C3_1 0.0177(5) 0.0239(5) 0.0231(5) -0.0059(4) 0.0024(4) -0.0001(4) C4_1 0.0156(5) 0.0199(5) 0.0185(5) -0.0010(4) 0.0014(4) 0.0008(4) C5_1 0.0140(4) 0.0187(5) 0.0161(4) 0.0006(3) 0.0027(3) 0.0004(3) C6_1 0.0141(4) 0.0180(5) 0.0176(4) 0.0004(3) 0.0017(3) 0.0013(3) C7_1 0.0151(4) 0.0219(5) 0.0198(5) -0.0026(4) 0.0010(4) 0.0008(4) C8_1 0.0169(5) 0.0212(5) 0.0267(5) -0.0050(4) 0.0012(4) -0.0010(4) C9_1 0.0172(5) 0.0192(5) 0.0253(5) -0.0015(4) 0.0043(4) -0.0006(4) C10_1 0.0162(4) 0.0178(5) 0.0169(4) -0.0002(3) -0.0001(3) -0.0008(3) C11_1 0.0246(5) 0.0236(5) 0.0232(5) 0.0031(4) 0.0072(4) 0.0012(4) C12_1 0.0310(6) 0.0215(5) 0.0238(5) 0.0056(4) 0.0022(4) -0.0012(4) C13_1 0.0222(5) 0.0166(5) 0.0237(5) -0.0005(4) -0.0069(4) 0.0016(4) C14_1 0.0172(5) 0.0223(5) 0.0243(5) -0.0015(4) -0.0005(4) 0.0027(4) C15_1 0.0171(5) 0.0205(5) 0.0211(5) 0.0023(4) 0.0013(4) 0.0007(4) C16_1 0.0223(6) 0.0407(7) 0.0251(6) 0.0003(5) -0.0050(4) 0.0068(5) C17_1 0.0236(6) 0.0224(6) 0.0418(7) -0.0113(5) -0.0022(5) 0.0011(4) C18_1 0.0217(5) 0.0272(6) 0.0276(6) -0.0031(4) -0.0085(4) 0.0033(4) C19_1 0.0260(6) 0.0185(5) 0.0402(7) 0.0003(5) 0.0014(5) 0.0012(4) B1_1 0.0155(5) 0.0199(5) 0.0210(5) 0.0031(4) 0.0021(4) 0.0011(4) F1_2 0.0169(3) 0.0259(3) 0.0300(4) 0.0037(3) 0.0051(3) -0.0041(2) F2_2 0.0306(4) 0.0205(3) 0.0271(4) -0.0094(3) 0.0008(3) -0.0002(3) O1_2 0.0383(6) 0.0255(5) 0.0528(6) -0.0201(4) 0.0007(5) -0.0039(4) O2_2 0.0281(4) 0.0277(4) 0.0317(5) 0.0045(4) -0.0012(4) -0.0128(3) N1_2 0.0151(4) 0.0165(4) 0.0182(4) -0.0007(3) -0.0007(3) -0.0026(3) N2_2 0.0165(4) 0.0150(4) 0.0219(4) 0.0000(3) 0.0001(3) -0.0010(3) N3_2 0.0254(5) 0.0160(4) 0.0246(5) 0.0007(3) -0.0051(4) -0.0040(3) C1_2 0.0169(5) 0.0237(5) 0.0198(5) 0.0002(4) -0.0013(4) -0.0037(4) C2_2 0.0218(5) 0.0237(5) 0.0255(5) 0.0067(4) -0.0051(4) -0.0032(4) C3_2 0.0198(5) 0.0190(5) 0.0240(5) 0.0043(4) -0.0023(4) -0.0035(4) C4_2 0.0150(4) 0.0157(4) 0.0188(5) 0.0003(4) 0.0001(3) -0.0021(3) C5_2 0.0133(4) 0.0156(4) 0.0162(4) -0.0012(3) 0.0018(3) -0.0017(3) C6_2 0.0143(4) 0.0160(4) 0.0191(5) -0.0006(3) 0.0004(3) -0.0015(3) C7_2 0.0165(5) 0.0211(5) 0.0229(5) 0.0023(4) -0.0009(4) -0.0005(4) C8_2 0.0193(5) 0.0220(5) 0.0314(6) 0.0068(4) -0.0034(4) 0.0005(4) C9_2 0.0188(5) 0.0166(5) 0.0307(6) 0.0030(4) 0.0009(4) 0.0009(4) C10_2 0.0152(4) 0.0154(4) 0.0157(4) -0.0008(3) -0.0001(3) -0.0021(3) C11_2 0.0176(5) 0.0180(5) 0.0231(5) -0.0024(4) 0.0050(4) -0.0018(4) C12_2 0.0251(5) 0.0165(5) 0.0234(5) -0.0041(4) 0.0067(4) -0.0014(4) C13_2 0.0202(5) 0.0139(4) 0.0168(4) 0.0004(3) -0.0014(4) -0.0036(3) C14_2 0.0143(4) 0.0199(5) 0.0214(5) -0.0010(4) 0.0012(4) -0.0027(4) C15_2 0.0163(5) 0.0181(5) 0.0201(5) -0.0038(4) 0.0026(4) -0.0017(4) C16_2 0.0243(6) 0.0292(6) 0.0261(6) -0.0016(5) -0.0064(4) -0.0080(4) C17_2 0.0359(7) 0.0211(5) 0.0386(7) 0.0109(5) -0.0122(5) -0.0080(5) C18_2 0.0250(6) 0.0285(6) 0.0269(6) 0.0029(5) -0.0101(4) -0.0043(4) C19_2 0.0314(6) 0.0166(5) 0.0453(8) 0.0047(5) -0.0033(5) -0.0022(4) B1_2 0.0155(5) 0.0153(5) 0.0196(5) -0.0026(4) 0.0012(4) -0.0025(4) _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 F1_1 B1_1 1.3986(13) . ? F2_1 B1_1 1.3865(13) . ? O1_1 N3_1 1.2315(15) . ? O2_1 N3_1 1.2283(16) . ? N1_1 C1_1 1.3525(14) . ? N1_1 C4_1 1.4036(13) . ? N1_1 B1_1 1.5512(15) . ? N2_1 C9_1 1.3493(14) . ? N2_1 C6_1 1.3964(13) . ? N2_1 B1_1 1.5467(15) . ? N3_1 C13_1 1.4740(14) . ? C1_1 C2_1 1.4061(17) . ? C1_1 C16_1 1.4917(16) . ? C2_1 C3_1 1.3870(16) . ? C3_1 C4_1 1.4308(15) . ? C3_1 C17_1 1.4973(17) . ? C4_1 C5_1 1.3966(14) . ? C5_1 C6_1 1.3993(14) . ? C5_1 C10_1 1.4936(14) . ? C6_1 C7_1 1.4301(14) . ? C7_1 C8_1 1.3901(15) . ? C7_1 C18_1 1.4977(15) . ? C8_1 C9_1 1.4064(16) . ? C9_1 C19_1 1.4927(15) . ? C10_1 C11_1 1.3912(15) . ? C10_1 C15_1 1.3941(15) . ? C11_1 C12_1 1.3944(16) . ? C12_1 C13_1 1.3852(17) . ? C13_1 C14_1 1.3845(16) . ? C14_1 C15_1 1.3926(15) . ? F1_2 B1_2 1.4004(13) . ? F2_2 B1_2 1.3892(13) . ? O1_2 N3_2 1.2275(14) . ? O2_2 N3_2 1.2250(13) . ? N1_2 C1_2 1.3492(13) . ? N1_2 C4_2 1.4022(13) . ? N1_2 B1_2 1.5413(15) . ? N2_2 C9_2 1.3451(14) . ? N2_2 C6_2 1.4019(13) . ? N2_2 B1_2 1.5440(14) . ? N3_2 C13_2 1.4724(13) . ? C1_2 C2_2 1.4046(15) . ? C1_2 C16_2 1.4879(15) . ? C2_2 C3_2 1.3857(15) . ? C3_2 C4_2 1.4275(14) . ? C3_2 C17_2 1.4958(16) . ? C4_2 C5_2 1.3999(14) . ? C5_2 C6_2 1.3964(14) . ? C5_2 C10_2 1.4904(13) . ? C6_2 C7_2 1.4336(14) . ? C7_2 C8_2 1.3837(15) . ? C7_2 C18_2 1.4992(16) . ? C8_2 C9_2 1.4078(16) . ? C9_2 C19_2 1.4912(16) . ? C10_2 C11_2 1.3941(14) . ? C10_2 C15_2 1.3961(14) . ? C11_2 C12_2 1.3879(14) . ? C12_2 C13_2 1.3802(15) . ? C13_2 C14_2 1.3839(14) . ? C14_2 C15_2 1.3920(14) . ? 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_1 N1_1 C4_1 108.24(9) . . ? C1_1 N1_1 B1_1 126.91(9) . . ? C4_1 N1_1 B1_1 124.66(9) . . ? C9_1 N2_1 C6_1 108.41(9) . . ? C9_1 N2_1 B1_1 126.08(9) . . ? C6_1 N2_1 B1_1 125.38(9) . . ? O2_1 N3_1 O1_1 123.77(11) . . ? O2_1 N3_1 C13_1 118.46(11) . . ? O1_1 N3_1 C13_1 117.77(11) . . ? N1_1 C1_1 C2_1 109.02(10) . . ? N1_1 C1_1 C16_1 123.69(11) . . ? C2_1 C1_1 C16_1 127.28(11) . . ? C3_1 C2_1 C1_1 108.76(10) . . ? C2_1 C3_1 C4_1 105.98(10) . . ? C2_1 C3_1 C17_1 124.82(11) . . ? C4_1 C3_1 C17_1 129.18(10) . . ? C5_1 C4_1 N1_1 120.16(9) . . ? C5_1 C4_1 C3_1 131.76(10) . . ? N1_1 C4_1 C3_1 108.00(9) . . ? C4_1 C5_1 C6_1 121.78(10) . . ? C4_1 C5_1 C10_1 118.84(9) . . ? C6_1 C5_1 C10_1 119.25(9) . . ? N2_1 C6_1 C5_1 119.93(9) . . ? N2_1 C6_1 C7_1 108.06(9) . . ? C5_1 C6_1 C7_1 131.98(10) . . ? C8_1 C7_1 C6_1 105.99(9) . . ? C8_1 C7_1 C18_1 124.46(10) . . ? C6_1 C7_1 C18_1 129.55(10) . . ? C7_1 C8_1 C9_1 108.35(10) . . ? N2_1 C9_1 C8_1 109.18(10) . . ? N2_1 C9_1 C19_1 123.08(10) . . ? C8_1 C9_1 C19_1 127.72(10) . . ? C11_1 C10_1 C15_1 120.38(10) . . ? C11_1 C10_1 C5_1 120.72(10) . . ? C15_1 C10_1 C5_1 118.88(9) . . ? C10_1 C11_1 C12_1 120.05(11) . . ? C13_1 C12_1 C11_1 118.24(10) . . ? C14_1 C13_1 C12_1 122.98(10) . . ? C14_1 C13_1 N3_1 118.24(11) . . ? C12_1 C13_1 N3_1 118.78(10) . . ? C13_1 C14_1 C15_1 118.06(10) . . ? C14_1 C15_1 C10_1 120.26(10) . . ? F2_1 B1_1 F1_1 109.28(9) . . ? F2_1 B1_1 N2_1 110.85(9) . . ? F1_1 B1_1 N2_1 109.19(9) . . ? F2_1 B1_1 N1_1 111.07(9) . . ? F1_1 B1_1 N1_1 109.51(9) . . ? N2_1 B1_1 N1_1 106.89(8) . . ? C1_2 N1_2 C4_2 108.62(9) . . ? C1_2 N1_2 B1_2 126.26(9) . . ? C4_2 N1_2 B1_2 125.11(8) . . ? C9_2 N2_2 C6_2 108.51(9) . . ? C9_2 N2_2 B1_2 125.92(9) . . ? C6_2 N2_2 B1_2 125.30(9) . . ? O2_2 N3_2 O1_2 123.83(10) . . ? O2_2 N3_2 C13_2 118.35(10) . . ? O1_2 N3_2 C13_2 117.82(10) . . ? N1_2 C1_2 C2_2 108.97(9) . . ? N1_2 C1_2 C16_2 123.80(10) . . ? C2_2 C1_2 C16_2 127.21(10) . . ? C3_2 C2_2 C1_2 108.43(10) . . ? C2_2 C3_2 C4_2 106.47(9) . . ? C2_2 C3_2 C17_2 124.05(10) . . ? C4_2 C3_2 C17_2 129.43(10) . . ? C5_2 C4_2 N1_2 120.21(9) . . ? C5_2 C4_2 C3_2 132.14(9) . . ? N1_2 C4_2 C3_2 107.49(9) . . ? C6_2 C5_2 C4_2 121.55(9) . . ? C6_2 C5_2 C10_2 119.24(9) . . ? C4_2 C5_2 C10_2 119.14(9) . . ? C5_2 C6_2 N2_2 119.88(9) . . ? C5_2 C6_2 C7_2 132.45(9) . . ? N2_2 C6_2 C7_2 107.66(9) . . ? C8_2 C7_2 C6_2 106.12(10) . . ? C8_2 C7_2 C18_2 124.02(10) . . ? C6_2 C7_2 C18_2 129.84(10) . . ? C7_2 C8_2 C9_2 108.53(10) . . ? N2_2 C9_2 C8_2 109.15(10) . . ? N2_2 C9_2 C19_2 123.14(11) . . ? C8_2 C9_2 C19_2 127.68(11) . . ? C11_2 C10_2 C15_2 119.84(9) . . ? C11_2 C10_2 C5_2 120.40(9) . . ? C15_2 C10_2 C5_2 119.75(9) . . ? C12_2 C11_2 C10_2 119.98(10) . . ? C13_2 C12_2 C11_2 118.96(10) . . ? C12_2 C13_2 C14_2 122.60(9) . . ? C12_2 C13_2 N3_2 118.36(9) . . ? C14_2 C13_2 N3_2 119.04(9) . . ? C13_2 C14_2 C15_2 118.02(10) . . ? C14_2 C15_2 C10_2 120.59(9) . . ? F2_2 B1_2 F1_2 109.10(9) . . ? F2_2 B1_2 N1_2 110.57(9) . . ? F1_2 B1_2 N1_2 109.92(9) . . ? F2_2 B1_2 N2_2 110.66(9) . . ? F1_2 B1_2 N2_2 109.50(9) . . ? N1_2 B1_2 N2_2 107.06(8) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.53 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.573 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.156