# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_KYMNo1-m _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 B F5 N2' _chemical_formula_sum 'C14 H14 B F5 N2' _chemical_formula_weight 316.08 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.4922(13) _cell_length_b 12.393(2) _cell_length_c 17.163(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1380.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 1673 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 20.80 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.137 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8739 _diffrn_reflns_av_R_equivalents 0.0740 _diffrn_reflns_av_sigmaI/netI 0.1150 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 26.01 _reflns_number_total 2715 _reflns_number_gt 1258 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.2000P)^2^+0.0000P] 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 2715 _refine_ls_number_parameters 203 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1757 _refine_ls_R_factor_gt 0.1080 _refine_ls_wR_factor_ref 0.3340 _refine_ls_wR_factor_gt 0.2822 _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_restrained_S_all 0.970 _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 B1 B 0.2934(16) 0.6513(8) 0.6520(6) 0.053(3) Uani 1 1 d . . . F1 F 0.2207(8) 0.5768(4) 0.5980(3) 0.0632(15) Uani 1 1 d . . . F2 F 0.4170(7) 0.7261(4) 0.6128(3) 0.0615(14) Uani 1 1 d . . . N1 N 0.4220(10) 0.5928(5) 0.7140(3) 0.0376(15) Uani 1 1 d . . . N2 N 0.1150(8) 0.7061(5) 0.6926(3) 0.0370(15) Uani 1 1 d . . . C1 C 0.5887(13) 0.5335(6) 0.7003(5) 0.048(2) Uani 1 1 d . . . C2 C 0.6777(15) 0.5131(8) 0.6215(6) 0.071(3) Uani 1 1 d . . . H2A H 0.5727 0.4804 0.5879 0.107 Uiso 1 1 calc R . . H2B H 0.7953 0.4639 0.6262 0.107 Uiso 1 1 calc R . . H2C H 0.7237 0.5814 0.5987 0.107 Uiso 1 1 calc R . . C3 C 0.6594(15) 0.4930(7) 0.7718(7) 0.069(3) Uani 1 1 d . . . H3 H 0.7739 0.4461 0.7779 0.082 Uiso 1 1 calc R . . C4 C 0.5389(14) 0.5312(7) 0.8321(5) 0.056(2) Uani 1 1 d . . . C5 C 0.5729(19) 0.4997(8) 0.9164(6) 0.082(3) Uani 1 1 d . . . H5A H 0.5639 0.4211 0.9215 0.123 Uiso 1 1 calc R . . H5B H 0.4672 0.5336 0.9490 0.123 Uiso 1 1 calc R . . H5C H 0.7095 0.5240 0.9332 0.123 Uiso 1 1 calc R . . C6 C 0.3805(12) 0.5965(7) 0.7941(5) 0.049(2) Uani 1 1 d . . . C7 C 0.2202(12) 0.6567(7) 0.8219(4) 0.048(2) Uani 1 1 d . . . C8 C 0.1961(16) 0.6749(12) 0.9108(8) 0.089(4) Uani 1 1 d . . . F3 F 0.0675(16) 0.6141(7) 0.9407(5) 0.132(3) Uani 1 1 d U . . F4 F 0.3600(16) 0.6874(6) 0.9466(3) 0.116(3) Uani 1 1 d . . . F5 F 0.1191(15) 0.7866(7) 0.9276(4) 0.134(3) Uani 1 1 d . . . C9 C 0.0788(13) 0.7115(6) 0.7730(4) 0.0431(18) Uani 1 1 d . . . C10 C -0.1033(12) 0.7731(6) 0.7865(4) 0.0457(19) Uani 1 1 d . . . C11 C -0.2216(17) 0.8071(9) 0.8573(5) 0.080(3) Uani 1 1 d . . . H11A H -0.1640 0.8746 0.8776 0.121 Uiso 1 1 calc R . . H11B H -0.2117 0.7509 0.8972 0.121 Uiso 1 1 calc R . . H11C H -0.3664 0.8182 0.8433 0.121 Uiso 1 1 calc R . . C12 C -0.1683(13) 0.8043(7) 0.7139(5) 0.057(2) Uani 1 1 d . . . H12 H -0.2863 0.8475 0.7038 0.068 Uiso 1 1 calc R . . C13 C -0.0343(12) 0.7628(6) 0.6561(4) 0.046(2) Uani 1 1 d . . . C14 C -0.0455(15) 0.7775(7) 0.5713(4) 0.059(2) Uani 1 1 d . . . H14A H 0.0682 0.8238 0.5542 0.089 Uiso 1 1 calc R . . H14B H -0.1770 0.8114 0.5576 0.089 Uiso 1 1 calc R . . H14C H -0.0350 0.7072 0.5455 0.089 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 0.056(6) 0.063(6) 0.041(5) 0.008(4) 0.000(5) 0.009(5) F1 0.069(3) 0.072(3) 0.048(3) -0.019(2) -0.003(2) 0.015(3) F2 0.059(3) 0.071(3) 0.054(3) 0.021(2) 0.012(2) 0.007(3) N1 0.038(3) 0.039(3) 0.036(4) 0.005(2) -0.001(3) -0.005(3) N2 0.035(3) 0.046(3) 0.030(3) -0.003(3) -0.002(2) -0.002(3) C1 0.046(5) 0.037(4) 0.060(5) -0.008(4) -0.010(4) -0.004(4) C2 0.057(6) 0.068(6) 0.089(8) -0.018(5) 0.016(5) 0.013(5) C3 0.052(6) 0.050(5) 0.104(8) 0.008(5) -0.035(6) -0.001(5) C4 0.057(5) 0.058(5) 0.053(5) 0.007(4) -0.015(5) -0.015(5) C5 0.103(8) 0.072(7) 0.070(6) 0.020(5) -0.042(6) 0.008(6) C6 0.047(5) 0.046(4) 0.055(5) 0.014(4) -0.014(4) -0.013(4) C7 0.037(4) 0.073(6) 0.034(4) 0.006(4) -0.003(3) -0.002(4) C8 0.036(5) 0.143(11) 0.089(9) 0.037(8) 0.017(6) 0.002(7) F3 0.140(4) 0.129(4) 0.126(4) 0.004(3) 0.017(3) -0.014(3) F4 0.188(9) 0.111(5) 0.049(4) -0.011(3) -0.011(4) -0.021(6) F5 0.163(8) 0.152(7) 0.085(5) -0.026(5) 0.025(5) -0.009(7) C9 0.055(5) 0.049(4) 0.026(4) -0.002(3) 0.000(3) -0.005(4) C10 0.043(5) 0.048(4) 0.045(5) -0.007(3) 0.011(4) 0.003(4) C11 0.098(8) 0.088(7) 0.055(6) 0.006(5) 0.021(5) 0.020(7) C12 0.044(5) 0.055(5) 0.071(6) 0.005(4) 0.004(4) 0.005(4) C13 0.051(5) 0.046(5) 0.040(4) 0.002(3) -0.010(4) 0.000(4) C14 0.066(6) 0.077(6) 0.034(5) 0.010(4) -0.012(4) 0.021(5) _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 F1 1.391(11) . ? B1 F2 1.399(10) . ? B1 N2 1.512(11) . ? B1 N1 1.534(11) . ? N1 C1 1.329(10) . ? N1 C6 1.401(10) . ? N2 C13 1.351(9) . ? N2 C9 1.402(9) . ? C1 C3 1.403(12) . ? C1 C2 1.492(12) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.381(14) . ? C3 H3 0.9500 . ? C4 C6 1.462(11) . ? C4 C5 1.515(12) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.366(11) . ? C7 C9 1.417(10) . ? C7 C8 1.552(16) . ? C8 F3 1.236(13) . ? C8 F4 1.238(13) . ? C8 F5 1.500(15) . ? C9 C10 1.426(10) . ? C10 C12 1.372(11) . ? C10 C11 1.498(11) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.416(11) . ? C12 H12 0.9500 . ? C13 C14 1.469(9) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 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 F1 B1 F2 108.3(7) . . ? F1 B1 N2 110.2(7) . . ? F2 B1 N2 111.3(7) . . ? F1 B1 N1 109.5(7) . . ? F2 B1 N1 109.5(7) . . ? N2 B1 N1 108.1(7) . . ? C1 N1 C6 110.4(6) . . ? C1 N1 B1 125.6(7) . . ? C6 N1 B1 124.0(7) . . ? C13 N2 C9 108.1(6) . . ? C13 N2 B1 124.8(6) . . ? C9 N2 B1 127.1(6) . . ? N1 C1 C3 108.0(8) . . ? N1 C1 C2 124.8(7) . . ? C3 C1 C2 127.3(9) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 C1 110.4(8) . . ? C4 C3 H3 124.8 . . ? C1 C3 H3 124.8 . . ? C3 C4 C6 104.7(8) . . ? C3 C4 C5 123.0(9) . . ? C6 C4 C5 132.2(9) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 N1 120.5(7) . . ? C7 C6 C4 133.0(8) . . ? N1 C6 C4 106.5(8) . . ? C6 C7 C9 123.3(7) . . ? C6 C7 C8 120.0(8) . . ? C9 C7 C8 116.6(8) . . ? F3 C8 F4 116.8(12) . . ? F3 C8 F5 105.0(9) . . ? F4 C8 F5 94.3(12) . . ? F3 C8 C7 112.8(12) . . ? F4 C8 C7 114.8(8) . . ? F5 C8 C7 110.9(9) . . ? N2 C9 C7 116.8(7) . . ? N2 C9 C10 109.0(6) . . ? C7 C9 C10 134.2(7) . . ? C12 C10 C9 104.9(6) . . ? C12 C10 C11 120.0(8) . . ? C9 C10 C11 135.1(8) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 C13 110.2(8) . . ? C10 C12 H12 124.9 . . ? C13 C12 H12 124.9 . . ? N2 C13 C12 107.8(7) . . ? N2 C13 C14 124.0(8) . . ? C12 C13 C14 128.2(8) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 F1 B1 N1 C1 58.4(10) . . . . ? F2 B1 N1 C1 -60.2(10) . . . . ? N2 B1 N1 C1 178.4(6) . . . . ? F1 B1 N1 C6 -122.8(8) . . . . ? F2 B1 N1 C6 118.6(8) . . . . ? N2 B1 N1 C6 -2.8(10) . . . . ? F1 B1 N2 C13 -58.4(10) . . . . ? F2 B1 N2 C13 61.7(10) . . . . ? N1 B1 N2 C13 -177.9(6) . . . . ? F1 B1 N2 C9 124.4(8) . . . . ? F2 B1 N2 C9 -115.5(8) . . . . ? N1 B1 N2 C9 4.8(11) . . . . ? C6 N1 C1 C3 1.8(8) . . . . ? B1 N1 C1 C3 -179.3(7) . . . . ? C6 N1 C1 C2 -179.6(7) . . . . ? B1 N1 C1 C2 -0.6(12) . . . . ? N1 C1 C3 C4 -2.4(9) . . . . ? C2 C1 C3 C4 179.1(8) . . . . ? C1 C3 C4 C6 1.9(9) . . . . ? C1 C3 C4 C5 178.4(8) . . . . ? C1 N1 C6 C7 177.4(7) . . . . ? B1 N1 C6 C7 -1.5(11) . . . . ? C1 N1 C6 C4 -0.6(8) . . . . ? B1 N1 C6 C4 -179.6(7) . . . . ? C3 C4 C6 C7 -178.5(9) . . . . ? C5 C4 C6 C7 5.5(16) . . . . ? C3 C4 C6 N1 -0.8(9) . . . . ? C5 C4 C6 N1 -176.8(9) . . . . ? N1 C6 C7 C9 4.8(12) . . . . ? C4 C6 C7 C9 -177.7(8) . . . . ? N1 C6 C7 C8 -170.3(8) . . . . ? C4 C6 C7 C8 7.1(14) . . . . ? C6 C7 C8 F3 -99.6(11) . . . . ? C9 C7 C8 F3 85.0(12) . . . . ? C6 C7 C8 F4 37.6(16) . . . . ? C9 C7 C8 F4 -137.9(11) . . . . ? C6 C7 C8 F5 143.0(9) . . . . ? C9 C7 C8 F5 -32.5(12) . . . . ? C13 N2 C9 C7 -179.9(6) . . . . ? B1 N2 C9 C7 -2.4(11) . . . . ? C13 N2 C9 C10 0.9(8) . . . . ? B1 N2 C9 C10 178.5(7) . . . . ? C6 C7 C9 N2 -2.9(12) . . . . ? C8 C7 C9 N2 172.4(8) . . . . ? C6 C7 C9 C10 176.0(8) . . . . ? C8 C7 C9 C10 -8.7(14) . . . . ? N2 C9 C10 C12 -1.0(8) . . . . ? C7 C9 C10 C12 180.0(9) . . . . ? N2 C9 C10 C11 179.7(10) . . . . ? C7 C9 C10 C11 0.8(16) . . . . ? C9 C10 C12 C13 0.8(9) . . . . ? C11 C10 C12 C13 -179.8(8) . . . . ? C9 N2 C13 C12 -0.4(9) . . . . ? B1 N2 C13 C12 -178.0(7) . . . . ? C9 N2 C13 C14 178.6(8) . . . . ? B1 N2 C13 C14 1.0(12) . . . . ? C10 C12 C13 N2 -0.3(10) . . . . ? C10 C12 C13 C14 -179.2(8) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.271 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.110 _database_code_depnum_ccdc_archive 'CCDC 958028' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_BDPCH3 _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H17 B F2 N2' _chemical_formula_sum 'C14 H17 B F2 N2' _chemical_formula_weight 262.11 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 Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 11.3274(11) _cell_length_b 7.1032(6) _cell_length_c 16.0113(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1288.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 4101 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 28.29 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9171 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 28.33 _reflns_number_total 1734 _reflns_number_gt 1098 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0933P)^2^+0.0903P] 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 1734 _refine_ls_number_parameters 117 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0869 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1736 _refine_ls_wR_factor_gt 0.1253 _refine_ls_goodness_of_fit_ref 1.151 _refine_ls_restrained_S_all 1.151 _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 B1 B 0.7511(2) 0.2500 0.59100(17) 0.0371(6) Uani 1 2 d S . . F1 F 0.80030(9) 0.09094(17) 0.62746(7) 0.0572(4) Uani 1 1 d . . . N1 N 0.61626(16) 0.2500 0.60291(11) 0.0323(5) Uani 1 2 d S . . N2 N 0.77414(17) 0.2500 0.49644(12) 0.0327(5) Uani 1 2 d S . . C1 C 0.5582(2) 0.2500 0.67681(14) 0.0370(6) Uani 1 2 d S . . C2 C 0.4372(2) 0.2500 0.66164(15) 0.0395(6) Uani 1 2 d S . . H2 H 0.3774 0.2500 0.7032 0.047 Uiso 1 2 calc SR . . C3 C 0.4182(2) 0.2500 0.57640(15) 0.0361(6) Uani 1 2 d S . . C4 C 0.5320(2) 0.2500 0.53833(13) 0.0310(5) Uani 1 2 d S . . C5 C 0.6187(3) 0.2500 0.75926(16) 0.0482(7) Uani 1 2 d S . . H5A H 0.6851 0.1617 0.7579 0.072 Uiso 0.50 1 calc PR . . H5B H 0.5628 0.2114 0.8027 0.072 Uiso 0.50 1 calc PR . . H5C H 0.6479 0.3769 0.7715 0.072 Uiso 0.50 1 calc PR . . C6 C 0.2983(2) 0.2500 0.53689(18) 0.0452(6) Uani 1 2 d S . . H6A H 0.2384 0.2243 0.5796 0.068 Uiso 0.50 1 calc PR . . H6B H 0.2949 0.1524 0.4937 0.068 Uiso 0.50 1 calc PR . . H6C H 0.2831 0.3733 0.5116 0.068 Uiso 0.50 1 calc PR . . C7 C 0.5678(2) 0.2500 0.45442(14) 0.0327(5) Uani 1 2 d S . . C8 C 0.4762(2) 0.2500 0.38743(14) 0.0412(6) Uani 1 2 d S . . H8A H 0.4523 0.3798 0.3754 0.062 Uiso 0.50 1 calc PR . . H8B H 0.4075 0.1776 0.4061 0.062 Uiso 0.50 1 calc PR . . H8C H 0.5088 0.1926 0.3368 0.062 Uiso 0.50 1 calc PR . . C9 C 0.6876(2) 0.2500 0.43352(14) 0.0319(5) Uani 1 2 d S . . C10 C 0.7472(2) 0.2500 0.35523(14) 0.0384(6) Uani 1 2 d S . . C11 C 0.8668(2) 0.2500 0.37338(16) 0.0441(6) Uani 1 2 d S . . H11 H 0.9287 0.2500 0.3334 0.053 Uiso 1 2 calc SR . . C12 C 0.8816(2) 0.2500 0.45974(15) 0.0377(6) Uani 1 2 d S . . C13 C 0.6975(3) 0.2500 0.26829(16) 0.0500(7) Uani 1 2 d S . . H13A H 0.6389 0.3508 0.2631 0.075 Uiso 0.50 1 calc PR . . H13B H 0.6598 0.1284 0.2571 0.075 Uiso 0.50 1 calc PR . . H13C H 0.7613 0.2707 0.2280 0.075 Uiso 0.50 1 calc PR . . C14 C 0.9939(2) 0.2500 0.50754(18) 0.0490(7) Uani 1 2 d S . . H14A H 1.0062 0.1258 0.5327 0.074 Uiso 0.50 1 calc PR . . H14B H 0.9901 0.3455 0.5516 0.074 Uiso 0.50 1 calc PR . . H14C H 1.0596 0.2788 0.4698 0.074 Uiso 0.50 1 calc PR . . 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 0.0333(14) 0.0452(14) 0.0327(13) 0.000 -0.0021(11) 0.000 F1 0.0471(7) 0.0782(9) 0.0464(7) 0.0221(5) 0.0010(5) 0.0195(5) N1 0.0312(10) 0.0374(10) 0.0281(10) 0.000 -0.0014(8) 0.000 N2 0.0316(10) 0.0348(10) 0.0315(10) 0.000 -0.0026(8) 0.000 C1 0.0385(13) 0.0428(13) 0.0297(12) 0.000 -0.0010(10) 0.000 C2 0.0359(13) 0.0463(13) 0.0362(12) 0.000 0.0059(10) 0.000 C3 0.0312(12) 0.0366(12) 0.0404(13) 0.000 -0.0027(10) 0.000 C4 0.0319(12) 0.0308(11) 0.0303(11) 0.000 -0.0038(9) 0.000 C5 0.0453(15) 0.0653(17) 0.0340(13) 0.000 -0.0011(11) 0.000 C6 0.0342(14) 0.0556(15) 0.0459(15) 0.000 -0.0024(10) 0.000 C7 0.0341(12) 0.0299(11) 0.0340(12) 0.000 -0.0032(9) 0.000 C8 0.0375(13) 0.0512(14) 0.0347(13) 0.000 -0.0051(10) 0.000 C9 0.0354(12) 0.0297(10) 0.0305(12) 0.000 -0.0022(9) 0.000 C10 0.0460(14) 0.0387(12) 0.0305(12) 0.000 0.0008(10) 0.000 C11 0.0411(14) 0.0523(14) 0.0389(13) 0.000 0.0086(11) 0.000 C12 0.0322(13) 0.0413(12) 0.0396(13) 0.000 0.0031(10) 0.000 C13 0.0553(17) 0.0624(17) 0.0324(14) 0.000 0.0028(12) 0.000 C14 0.0338(14) 0.0609(17) 0.0523(16) 0.000 0.0005(11) 0.000 _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 F1 1.3885(19) 7_565 ? B1 F1 1.3885(19) . ? B1 N2 1.536(3) . ? B1 N1 1.539(3) . ? N1 C1 1.354(3) . ? N1 C4 1.408(3) . ? N2 C12 1.352(3) . ? N2 C9 1.406(3) . ? C1 C2 1.392(3) . ? C1 C5 1.487(3) . ? C2 C3 1.382(4) . ? C2 H2 0.9500 . ? C3 C4 1.425(3) . ? C3 C6 1.499(3) . ? C4 C7 1.404(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C9 1.397(3) . ? C7 C8 1.492(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.424(3) . ? C10 C11 1.385(4) . ? C10 C13 1.502(3) . ? C11 C12 1.393(3) . ? C11 H11 0.9500 . ? C12 C14 1.485(4) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 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 F1 B1 F1 108.9(2) 7_565 . ? F1 B1 N2 110.26(14) 7_565 . ? F1 B1 N2 110.26(14) . . ? F1 B1 N1 110.25(14) 7_565 . ? F1 B1 N1 110.25(14) . . ? N2 B1 N1 106.89(19) . . ? C1 N1 C4 108.23(19) . . ? C1 N1 B1 126.16(19) . . ? C4 N1 B1 125.61(18) . . ? C12 N2 C9 108.4(2) . . ? C12 N2 B1 125.5(2) . . ? C9 N2 B1 126.01(19) . . ? N1 C1 C2 109.0(2) . . ? N1 C1 C5 123.5(2) . . ? C2 C1 C5 127.5(2) . . ? C3 C2 C1 109.0(2) . . ? C3 C2 H2 125.5 . . ? C1 C2 H2 125.5 . . ? C2 C3 C4 106.4(2) . . ? C2 C3 C6 123.9(2) . . ? C4 C3 C6 129.7(2) . . ? C7 C4 N1 120.4(2) . . ? C7 C4 C3 132.2(2) . . ? N1 C4 C3 107.40(19) . . ? C1 C5 H5A 109.5 . . ? C1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C9 C7 C4 120.7(2) . . ? C9 C7 C8 120.2(2) . . ? C4 C7 C8 119.1(2) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 N2 120.4(2) . . ? C7 C9 C10 132.2(2) . . ? N2 C9 C10 107.5(2) . . ? C11 C10 C9 106.2(2) . . ? C11 C10 C13 124.1(2) . . ? C9 C10 C13 129.6(2) . . ? C10 C11 C12 109.0(2) . . ? C10 C11 H11 125.5 . . ? C12 C11 H11 125.5 . . ? N2 C12 C11 108.8(2) . . ? N2 C12 C14 123.2(2) . . ? C11 C12 C14 128.0(2) . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 F1 B1 N1 C1 -60.15(15) 7_565 . . . ? F1 B1 N1 C1 60.15(15) . . . . ? N2 B1 N1 C1 180.0 . . . . ? F1 B1 N1 C4 119.85(15) 7_565 . . . ? F1 B1 N1 C4 -119.85(15) . . . . ? N2 B1 N1 C4 0.0 . . . . ? F1 B1 N2 C12 60.16(15) 7_565 . . . ? F1 B1 N2 C12 -60.16(15) . . . . ? N1 B1 N2 C12 180.0 . . . . ? F1 B1 N2 C9 -119.84(15) 7_565 . . . ? F1 B1 N2 C9 119.84(15) . . . . ? N1 B1 N2 C9 0.0 . . . . ? C4 N1 C1 C2 0.0 . . . . ? B1 N1 C1 C2 180.0 . . . . ? C4 N1 C1 C5 180.0 . . . . ? B1 N1 C1 C5 0.0 . . . . ? N1 C1 C2 C3 0.0 . . . . ? C5 C1 C2 C3 180.0 . . . . ? C1 C2 C3 C4 0.0 . . . . ? C1 C2 C3 C6 180.0 . . . . ? C1 N1 C4 C7 180.0 . . . . ? B1 N1 C4 C7 0.0 . . . . ? C1 N1 C4 C3 0.0 . . . . ? B1 N1 C4 C3 180.0 . . . . ? C2 C3 C4 C7 180.0 . . . . ? C6 C3 C4 C7 0.0 . . . . ? C2 C3 C4 N1 0.0 . . . . ? C6 C3 C4 N1 180.0 . . . . ? N1 C4 C7 C9 0.0 . . . . ? C3 C4 C7 C9 180.0 . . . . ? N1 C4 C7 C8 180.0 . . . . ? C3 C4 C7 C8 0.0 . . . . ? C4 C7 C9 N2 0.0 . . . . ? C8 C7 C9 N2 180.0 . . . . ? C4 C7 C9 C10 180.0 . . . . ? C8 C7 C9 C10 0.0 . . . . ? C12 N2 C9 C7 180.0 . . . . ? B1 N2 C9 C7 0.0 . . . . ? C12 N2 C9 C10 0.0 . . . . ? B1 N2 C9 C10 180.0 . . . . ? C7 C9 C10 C11 180.0 . . . . ? N2 C9 C10 C11 0.0 . . . . ? C7 C9 C10 C13 0.0 . . . . ? N2 C9 C10 C13 180.0 . . . . ? C9 C10 C11 C12 0.0 . . . . ? C13 C10 C11 C12 180.0 . . . . ? C9 N2 C12 C11 0.0 . . . . ? B1 N2 C12 C11 180.0 . . . . ? C9 N2 C12 C14 180.0 . . . . ? B1 N2 C12 C14 0.0 . . . . ? C10 C11 C12 N2 0.0 . . . . ? C10 C11 C12 C14 180.0 . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.426 _refine_diff_density_min -0.513 _refine_diff_density_rms 0.191 _database_code_depnum_ccdc_archive 'CCDC 958029'