data_vn1104m _audit_creation_method SHELXL-97 _chemical_name_systematic ; II-VKN-91 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C20 H14 N3) (B F4) ; _chemical_formula_sum 'C20 H14 B F4 N3' _chemical_formula_weight 383.15 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 11.0318(6) _cell_length_b 6.8167(3) _cell_length_c 21.8563(11) _cell_angle_alpha 90.00 _cell_angle_beta 94.287(2) _cell_angle_gamma 90.00 _cell_volume 1639.01(14) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8137 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 33.20 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9660 _exptl_absorpt_correction_T_max 0.9707 _exptl_absorpt_process_details 'SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 23114 _diffrn_reflns_av_R_equivalents 0.0571 _diffrn_reflns_av_sigmaI/netI 0.0523 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 32.58 _reflns_number_total 5967 _reflns_number_gt 4794 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0800P)^2^+0.1000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5967 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1422 _refine_ls_wR_factor_gt 0.1328 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _refine_ls_shift/su_max 0.001 _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 B1 B 0.33413(10) 0.01909(18) 0.57643(5) 0.0205(2) Uani 1 1 d . . . F1 F 0.40178(6) 0.14090(11) 0.53951(3) 0.03125(17) Uani 1 1 d . . . F2 F 0.33269(6) -0.17089(10) 0.55255(3) 0.03048(17) Uani 1 1 d . . . F3 F 0.21637(6) 0.09145(11) 0.57612(3) 0.02800(16) Uani 1 1 d . . . F4 F 0.38935(6) 0.01479(10) 0.63534(3) 0.02749(16) Uani 1 1 d . . . N11 N 0.14206(7) 0.35573(11) 0.27910(4) 0.01587(16) Uani 1 1 d . . . C12 C 0.25487(8) 0.36573(13) 0.26617(4) 0.01435(17) Uani 1 1 d . . . N13 N 0.35372(7) 0.37037(11) 0.31139(4) 0.01433(15) Uani 1 1 d . . . C14 C 0.33131(8) 0.32375(13) 0.37077(4) 0.01484(17) Uani 1 1 d . . . N14 N 0.42026(7) 0.27584(13) 0.41170(4) 0.01897(17) Uani 1 1 d . . . H14A H 0.4035(13) 0.235(2) 0.4484(7) 0.023 Uiso 1 1 d . . . H14B H 0.4960(14) 0.256(2) 0.4019(6) 0.023 Uiso 1 1 d . . . C15 C 0.20741(8) 0.32731(13) 0.38708(4) 0.01536(17) Uani 1 1 d . . . C16 C 0.17619(9) 0.30870(14) 0.44812(4) 0.01861(18) Uani 1 1 d . . . H16 H 0.2379 0.2959 0.4806 0.022 Uiso 1 1 calc R . . C17 C 0.05559(9) 0.30921(15) 0.46031(5) 0.02073(19) Uani 1 1 d . . . H17 H 0.0343 0.2963 0.5014 0.025 Uiso 1 1 calc R . . C18 C -0.03657(9) 0.32860(15) 0.41269(5) 0.02115(19) Uani 1 1 d . . . H18 H -0.1194 0.3283 0.4218 0.025 Uiso 1 1 calc R . . C19 C -0.00720(8) 0.34801(14) 0.35286(5) 0.01878(18) Uani 1 1 d . . . H19 H -0.0696 0.3618 0.3208 0.023 Uiso 1 1 calc R . . C20 C 0.11578(8) 0.34731(13) 0.33943(4) 0.01557(17) Uani 1 1 d . . . C21 C 0.49944(8) 0.39525(13) 0.23194(4) 0.01534(17) Uani 1 1 d . . . C22 C 0.47418(8) 0.41887(13) 0.29363(4) 0.01486(17) Uani 1 1 d . . . C23 C 0.55984(8) 0.50427(14) 0.33578(4) 0.01758(18) Uani 1 1 d . . . H23 H 0.5390 0.5332 0.3762 0.021 Uiso 1 1 calc R . . C24 C 0.67559(9) 0.54687(15) 0.31850(5) 0.02023(19) Uani 1 1 d . . . H24 H 0.7342 0.6031 0.3474 0.024 Uiso 1 1 calc R . . C25 C 0.70590(8) 0.50757(15) 0.25913(5) 0.02020(19) Uani 1 1 d . . . H25 H 0.7865 0.5288 0.2480 0.024 Uiso 1 1 calc R . . C26 C 0.61785(8) 0.43731(14) 0.21632(4) 0.01836(18) Uani 1 1 d . . . H26 H 0.6380 0.4170 0.1753 0.022 Uiso 1 1 calc R . . C31 C 0.40169(8) 0.35560(13) 0.18470(4) 0.01535(17) Uani 1 1 d . . . C32 C 0.28146(8) 0.35811(12) 0.20175(4) 0.01446(17) Uani 1 1 d . . . C33 C 0.18321(9) 0.34410(13) 0.15697(4) 0.01746(18) Uani 1 1 d . . . H33 H 0.1021 0.3481 0.1688 0.021 Uiso 1 1 calc R . . C34 C 0.20484(9) 0.32453(14) 0.09576(4) 0.01865(18) Uani 1 1 d . . . H34 H 0.1387 0.3150 0.0655 0.022 Uiso 1 1 calc R . . C35 C 0.32453(9) 0.31878(14) 0.07864(4) 0.01921(18) Uani 1 1 d . . . H35 H 0.3393 0.3041 0.0366 0.023 Uiso 1 1 calc R . . C36 C 0.42163(9) 0.33420(14) 0.12226(4) 0.01811(18) Uani 1 1 d . . . H36 H 0.5024 0.3303 0.1099 0.022 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 B1 0.0156(4) 0.0290(5) 0.0169(5) 0.0022(4) 0.0009(3) 0.0023(4) F1 0.0197(3) 0.0457(4) 0.0287(3) 0.0127(3) 0.0042(2) -0.0010(3) F2 0.0275(3) 0.0332(4) 0.0301(4) -0.0076(3) -0.0024(3) 0.0033(3) F3 0.0179(3) 0.0417(4) 0.0249(3) 0.0061(3) 0.0051(2) 0.0081(3) F4 0.0269(3) 0.0369(4) 0.0179(3) 0.0004(2) -0.0035(2) 0.0022(3) N11 0.0131(3) 0.0184(4) 0.0163(4) -0.0001(3) 0.0023(3) -0.0003(3) C12 0.0127(4) 0.0137(4) 0.0166(4) 0.0004(3) 0.0009(3) 0.0002(3) N13 0.0121(3) 0.0164(3) 0.0145(3) 0.0004(3) 0.0009(2) 0.0006(2) C14 0.0147(4) 0.0149(4) 0.0150(4) 0.0004(3) 0.0014(3) 0.0001(3) N14 0.0146(3) 0.0253(4) 0.0171(4) 0.0042(3) 0.0012(3) 0.0019(3) C15 0.0136(4) 0.0161(4) 0.0166(4) 0.0006(3) 0.0026(3) 0.0008(3) C16 0.0180(4) 0.0214(4) 0.0169(4) 0.0016(3) 0.0040(3) 0.0014(3) C17 0.0203(4) 0.0241(4) 0.0186(4) 0.0010(3) 0.0067(3) 0.0013(3) C18 0.0158(4) 0.0239(4) 0.0246(5) -0.0003(4) 0.0070(3) 0.0001(3) C19 0.0135(4) 0.0220(4) 0.0210(4) -0.0009(3) 0.0024(3) -0.0001(3) C20 0.0141(4) 0.0156(4) 0.0173(4) -0.0004(3) 0.0027(3) 0.0001(3) C21 0.0139(4) 0.0152(4) 0.0170(4) 0.0004(3) 0.0020(3) 0.0011(3) C22 0.0122(3) 0.0151(4) 0.0175(4) 0.0013(3) 0.0024(3) 0.0004(3) C23 0.0153(4) 0.0190(4) 0.0183(4) 0.0001(3) 0.0004(3) -0.0010(3) C24 0.0150(4) 0.0222(4) 0.0233(5) 0.0000(3) -0.0001(3) -0.0016(3) C25 0.0138(4) 0.0226(4) 0.0244(5) 0.0035(4) 0.0027(3) -0.0002(3) C26 0.0152(4) 0.0209(4) 0.0192(4) 0.0011(3) 0.0034(3) 0.0017(3) C31 0.0163(4) 0.0137(4) 0.0162(4) 0.0008(3) 0.0025(3) 0.0013(3) C32 0.0155(4) 0.0138(4) 0.0142(4) 0.0011(3) 0.0020(3) 0.0005(3) C33 0.0162(4) 0.0179(4) 0.0182(4) 0.0006(3) 0.0006(3) -0.0008(3) C34 0.0192(4) 0.0195(4) 0.0170(4) 0.0004(3) -0.0005(3) -0.0008(3) C35 0.0211(4) 0.0207(4) 0.0159(4) -0.0010(3) 0.0020(3) 0.0008(3) C36 0.0178(4) 0.0195(4) 0.0174(4) -0.0002(3) 0.0036(3) 0.0007(3) _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 B1 F4 1.3831(13) . ? B1 F3 1.3892(12) . ? B1 F2 1.3959(14) . ? B1 F1 1.4097(13) . ? N11 C12 1.2984(11) . ? N11 C20 1.3722(12) . ? C12 N13 1.4164(12) . ? C12 C32 1.4604(13) . ? N13 C14 1.3763(12) . ? N13 C22 1.4502(11) . ? C14 N14 1.3186(12) . ? C14 C15 1.4384(12) . ? N14 H14A 0.882(14) . ? N14 H14B 0.888(15) . ? C15 C20 1.4027(13) . ? C15 C16 1.4083(13) . ? C16 C17 1.3762(13) . ? C16 H16 0.9500 . ? C17 C18 1.4059(15) . ? C17 H17 0.9500 . ? C18 C19 1.3768(14) . ? C18 H18 0.9500 . ? C19 C20 1.4094(12) . ? C19 H19 0.9500 . ? C21 C26 1.4041(12) . ? C21 C22 1.4065(13) . ? C21 C31 1.4613(13) . ? C22 C23 1.3965(13) . ? C23 C24 1.3891(13) . ? C23 H23 0.9500 . ? C24 C25 1.3899(14) . ? C24 H24 0.9500 . ? C25 C26 1.3830(14) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 C32 1.4043(12) . ? C31 C36 1.4060(13) . ? C32 C33 1.4083(13) . ? C33 C34 1.3829(14) . ? C33 H33 0.9500 . ? C34 C35 1.3997(13) . ? C34 H34 0.9500 . ? C35 C36 1.3838(14) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? 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 F4 B1 F3 111.02(8) . . ? F4 B1 F2 108.68(9) . . ? F3 B1 F2 110.06(9) . . ? F4 B1 F1 109.28(9) . . ? F3 B1 F1 108.84(9) . . ? F2 B1 F1 108.92(9) . . ? C12 N11 C20 119.09(8) . . ? N11 C12 N13 123.35(8) . . ? N11 C12 C32 118.23(8) . . ? N13 C12 C32 118.28(8) . . ? C14 N13 C12 118.01(7) . . ? C14 N13 C22 122.53(8) . . ? C12 N13 C22 119.44(7) . . ? N14 C14 N13 121.32(8) . . ? N14 C14 C15 120.58(8) . . ? N13 C14 C15 118.09(8) . . ? C14 N14 H14A 119.9(9) . . ? C14 N14 H14B 122.7(9) . . ? H14A N14 H14B 115.9(13) . . ? C20 C15 C16 119.90(8) . . ? C20 C15 C14 117.58(8) . . ? C16 C15 C14 122.52(8) . . ? C17 C16 C15 119.44(9) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C18 120.86(9) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C19 C18 C17 120.24(9) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C20 119.74(9) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? N11 C20 C15 121.68(8) . . ? N11 C20 C19 118.41(8) . . ? C15 C20 C19 119.81(9) . . ? C26 C21 C22 117.67(8) . . ? C26 C21 C31 121.12(8) . . ? C22 C21 C31 120.65(8) . . ? C23 C22 C21 120.49(8) . . ? C23 C22 N13 120.46(8) . . ? C21 C22 N13 118.80(8) . . ? C24 C23 C22 119.88(9) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C23 C24 C25 120.25(9) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C26 C25 C24 119.51(9) . . ? C26 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? C25 C26 C21 121.69(9) . . ? C25 C26 H26 119.2 . . ? C21 C26 H26 119.2 . . ? C32 C31 C36 118.57(8) . . ? C32 C31 C21 118.17(8) . . ? C36 C31 C21 122.96(8) . . ? C31 C32 C33 120.52(8) . . ? C31 C32 C12 121.20(8) . . ? C33 C32 C12 118.21(8) . . ? C34 C33 C32 119.96(8) . . ? C34 C33 H33 120.0 . . ? C32 C33 H33 120.0 . . ? C33 C34 C35 119.72(9) . . ? C33 C34 H34 120.1 . . ? C35 C34 H34 120.1 . . ? C36 C35 C34 120.71(9) . . ? C36 C35 H35 119.6 . . ? C34 C35 H35 119.6 . . ? C35 C36 C31 120.49(9) . . ? C35 C36 H36 119.8 . . ? C31 C36 H36 119.8 . . ? 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 C20 N11 C12 N13 -0.62(13) . . . . ? C20 N11 C12 C32 174.99(8) . . . . ? N11 C12 N13 C14 13.11(12) . . . . ? C32 C12 N13 C14 -162.50(8) . . . . ? N11 C12 N13 C22 -168.33(8) . . . . ? C32 C12 N13 C22 16.06(11) . . . . ? C12 N13 C14 N14 162.41(9) . . . . ? C22 N13 C14 N14 -16.11(13) . . . . ? C12 N13 C14 C15 -17.17(12) . . . . ? C22 N13 C14 C15 164.32(8) . . . . ? N14 C14 C15 C20 -169.66(9) . . . . ? N13 C14 C15 C20 9.92(12) . . . . ? N14 C14 C15 C16 9.38(14) . . . . ? N13 C14 C15 C16 -171.04(8) . . . . ? C20 C15 C16 C17 0.38(14) . . . . ? C14 C15 C16 C17 -178.64(8) . . . . ? C15 C16 C17 C18 -0.18(15) . . . . ? C16 C17 C18 C19 -0.19(15) . . . . ? C17 C18 C19 C20 0.35(15) . . . . ? C12 N11 C20 C15 -7.19(13) . . . . ? C12 N11 C20 C19 176.37(8) . . . . ? C16 C15 C20 N11 -176.61(8) . . . . ? C14 C15 C20 N11 2.45(13) . . . . ? C16 C15 C20 C19 -0.22(13) . . . . ? C14 C15 C20 C19 178.85(8) . . . . ? C18 C19 C20 N11 176.36(9) . . . . ? C18 C19 C20 C15 -0.15(14) . . . . ? C26 C21 C22 C23 7.77(13) . . . . ? C31 C21 C22 C23 -163.74(9) . . . . ? C26 C21 C22 N13 -178.03(8) . . . . ? C31 C21 C22 N13 10.46(13) . . . . ? C14 N13 C22 C23 -28.62(12) . . . . ? C12 N13 C22 C23 152.89(8) . . . . ? C14 N13 C22 C21 157.18(8) . . . . ? C12 N13 C22 C21 -21.31(12) . . . . ? C21 C22 C23 C24 -7.02(14) . . . . ? N13 C22 C23 C24 178.88(8) . . . . ? C22 C23 C24 C25 0.98(15) . . . . ? C23 C24 C25 C26 4.05(15) . . . . ? C24 C25 C26 C21 -3.15(15) . . . . ? C22 C21 C26 C25 -2.71(14) . . . . ? C31 C21 C26 C25 168.76(9) . . . . ? C26 C21 C31 C32 -165.99(8) . . . . ? C22 C21 C31 C32 5.23(13) . . . . ? C26 C21 C31 C36 7.63(14) . . . . ? C22 C21 C31 C36 178.85(9) . . . . ? C36 C31 C32 C33 -1.48(13) . . . . ? C21 C31 C32 C33 172.43(8) . . . . ? C36 C31 C32 C12 175.56(8) . . . . ? C21 C31 C32 C12 -10.53(12) . . . . ? N11 C12 C32 C31 -175.90(8) . . . . ? N13 C12 C32 C31 -0.06(12) . . . . ? N11 C12 C32 C33 1.20(12) . . . . ? N13 C12 C32 C33 177.04(8) . . . . ? C31 C32 C33 C34 1.05(13) . . . . ? C12 C32 C33 C34 -176.07(8) . . . . ? C32 C33 C34 C35 -0.01(14) . . . . ? C33 C34 C35 C36 -0.57(14) . . . . ? C34 C35 C36 C31 0.12(14) . . . . ? C32 C31 C36 C35 0.90(13) . . . . ? C21 C31 C36 C35 -172.70(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N14 H14A F1 0.882(14) 2.093(15) 2.9625(11) 168.4(13) . N14 H14B F2 0.888(15) 2.148(15) 2.8691(11) 137.8(12) 3_656 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 32.58 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.452 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.067