# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email jides@kaist.ac.kr _publ_contact_author_name 'Dhiraj Murale' loop_ _publ_author_name 'Dhiraj Murale' K.Lee 'Kibong Kim' D.Churchill data_nchu43-1 _database_code_depnum_ccdc_archive 'CCDC 822264' #TrackingRef 'nchu43-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety C17H21BF2N2O _chemical_formula_sum 'C17 H21 B F2 N2 O' _chemical_formula_weight 318.17 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.0254(19) _cell_length_b 11.308(2) _cell_length_c 16.035(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.845(6) _cell_angle_gamma 90.00 _cell_volume 1632.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2652 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 24.30 _exptl_crystal_description platy _exptl_crystal_colour Darkred _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.930 _exptl_absorpt_correction_T_max 0.941 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 17948 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 24.30 _reflns_number_total 2652 _reflns_number_gt 1997 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker APEX II' _computing_data_reduction 'Bruker APEX II' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP3 _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^)+(0.0868P)^2^+1.3208P] 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 2652 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0815 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.1788 _refine_ls_wR_factor_gt 0.1630 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 B B 0.4459(4) 0.2413(3) 0.9373(2) 0.0456(8) Uani 1 1 d . . . O O 0.4342(2) 0.33852(19) 0.88013(12) 0.0559(6) Uani 1 1 d . . . F1 F 0.5598(2) 0.17018(18) 0.91712(12) 0.0791(7) Uani 1 1 d . . . F2 F 0.3130(2) 0.17495(18) 0.93130(13) 0.0758(6) Uani 1 1 d . . . N1 N 0.4681(2) 0.28312(19) 1.03065(13) 0.0410(6) Uani 1 1 d . . . N2 N 0.1202(3) 0.5456(2) 0.68377(16) 0.0547(7) Uani 1 1 d . . . C1 C 0.2527(3) 0.4709(2) 0.93534(17) 0.0445(7) Uani 1 1 d . . . C2 C 0.3171(3) 0.4120(3) 0.86783(17) 0.0451(7) Uani 1 1 d . . . C3 C 0.2702(3) 0.4358(3) 0.78659(18) 0.0476(7) Uani 1 1 d . . . H3 H 0.3111 0.3930 0.7442 0.057 Uiso 1 1 calc R . . C4 C 0.1626(3) 0.5223(3) 0.76461(18) 0.0464(7) Uani 1 1 d . . . C5 C 0.1016(3) 0.5839(3) 0.8316(2) 0.0555(8) Uani 1 1 d . . . H5 H 0.0309 0.6425 0.8201 0.067 Uiso 1 1 calc R . . C6 C 0.1453(3) 0.5579(3) 0.9119(2) 0.0533(8) Uani 1 1 d . . . H6 H 0.1023 0.5996 0.9541 0.064 Uiso 1 1 calc R . . C7 C 0.2923(3) 0.4530(3) 1.02098(18) 0.0464(7) Uani 1 1 d . . . H7 H 0.2453 0.5051 1.0555 0.056 Uiso 1 1 calc R . . C8 C 0.3855(3) 0.3752(2) 1.06436(17) 0.0432(7) Uani 1 1 d . . . C9 C 0.4164(3) 0.3744(3) 1.15344(17) 0.0489(7) Uani 1 1 d . . . C10 C 0.5155(3) 0.2853(3) 1.17043(18) 0.0528(8) Uani 1 1 d . . . H9 H 0.5562 0.2645 1.2232 0.063 Uiso 1 1 calc R . . C11 C 0.5458(3) 0.2301(3) 1.09475(17) 0.0476(7) Uani 1 1 d . . . C12 C 0.3518(4) 0.4576(3) 1.21410(19) 0.0639(9) Uani 1 1 d . . . H12A H 0.3769 0.4310 1.2701 0.096 Uiso 1 1 calc R . . H12B H 0.2458 0.4596 1.2041 0.096 Uiso 1 1 calc R . . H12C H 0.3914 0.5354 1.2069 0.096 Uiso 1 1 calc R . . C13 C 0.6478(4) 0.1283(3) 1.0859(2) 0.0692(10) Uani 1 1 d . . . H13A H 0.5914 0.0599 1.0679 0.104 Uiso 1 1 calc R . . H13B H 0.7002 0.1123 1.1388 0.104 Uiso 1 1 calc R . . H13C H 0.7177 0.1470 1.0453 0.104 Uiso 1 1 calc R . . C14 C 0.1812(4) 0.4797(3) 0.61519(19) 0.0582(9) Uani 1 1 d . . . H14A H 0.2864 0.4669 0.6283 0.070 Uiso 1 1 calc R . . H14B H 0.1705 0.5270 0.5647 0.070 Uiso 1 1 calc R . . C15 C 0.1064(4) 0.3618(4) 0.5990(3) 0.0785(11) Uani 1 1 d . . . H15A H 0.1227 0.3124 0.6474 0.118 Uiso 1 1 calc R . . H15B H 0.1473 0.3245 0.5519 0.118 Uiso 1 1 calc R . . H15C H 0.0017 0.3737 0.5874 0.118 Uiso 1 1 calc R . . C16 C 0.0114(4) 0.6382(3) 0.6591(2) 0.0710(10) Uani 1 1 d . . . H16A H -0.0624 0.6423 0.7003 0.085 Uiso 1 1 calc R . . H16B H -0.0392 0.6171 0.6059 0.085 Uiso 1 1 calc R . . C17 C 0.0819(5) 0.7577(4) 0.6515(4) 0.1066(17) Uani 1 1 d . . . H17A H 0.1264 0.7815 0.7049 0.160 Uiso 1 1 calc R . . H17B H 0.0076 0.8142 0.6328 0.160 Uiso 1 1 calc R . . H17C H 0.1569 0.7537 0.6118 0.160 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 B 0.047(2) 0.0445(19) 0.0447(18) -0.0029(15) 0.0000(14) 0.0059(16) O 0.0580(13) 0.0624(14) 0.0474(12) 0.0040(10) 0.0054(10) 0.0173(11) F1 0.0882(15) 0.0886(15) 0.0596(11) -0.0049(10) -0.0019(10) 0.0488(12) F2 0.0835(14) 0.0676(13) 0.0745(13) -0.0094(10) -0.0088(11) -0.0194(11) N1 0.0430(13) 0.0383(12) 0.0413(12) 0.0006(10) 0.0002(10) -0.0015(11) N2 0.0523(15) 0.0561(16) 0.0548(15) 0.0142(12) -0.0034(12) 0.0074(13) C1 0.0447(16) 0.0396(16) 0.0489(16) -0.0034(12) 0.0011(13) 0.0017(13) C2 0.0448(16) 0.0411(15) 0.0489(16) 0.0008(13) -0.0016(13) 0.0071(13) C3 0.0498(17) 0.0472(17) 0.0454(16) -0.0014(13) 0.0011(13) 0.0071(14) C4 0.0406(16) 0.0445(16) 0.0535(17) 0.0054(13) -0.0023(13) -0.0022(13) C5 0.0489(18) 0.0481(17) 0.069(2) 0.0037(15) -0.0021(15) 0.0153(15) C6 0.0570(19) 0.0457(18) 0.0573(19) -0.0083(14) 0.0057(15) 0.0077(15) C7 0.0472(17) 0.0445(16) 0.0481(16) -0.0095(13) 0.0073(13) -0.0023(14) C8 0.0430(16) 0.0442(16) 0.0423(15) -0.0035(13) 0.0025(12) -0.0065(13) C9 0.0522(18) 0.0527(18) 0.0423(15) -0.0028(13) 0.0054(13) -0.0150(15) C10 0.057(2) 0.0587(19) 0.0421(16) 0.0073(14) -0.0044(14) -0.0097(16) C11 0.0479(17) 0.0469(17) 0.0474(16) 0.0067(13) -0.0001(13) -0.0070(14) C12 0.071(2) 0.075(2) 0.0466(17) -0.0110(16) 0.0115(15) -0.0089(18) C13 0.078(2) 0.071(2) 0.058(2) 0.0116(18) -0.0043(17) 0.0182(19) C14 0.0543(18) 0.073(2) 0.0471(17) 0.0187(16) 0.0037(14) 0.0034(17) C15 0.076(3) 0.087(3) 0.072(2) -0.010(2) 0.0027(19) -0.013(2) C16 0.056(2) 0.090(3) 0.067(2) 0.026(2) 0.0006(17) 0.0207(19) C17 0.104(3) 0.070(3) 0.150(4) 0.051(3) 0.035(3) 0.035(2) _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 B F1 1.361(4) . ? B F2 1.412(4) . ? B O 1.431(4) . ? B N1 1.570(4) . ? O C2 1.348(3) . ? N1 C11 1.346(4) . ? N1 C8 1.409(4) . ? N2 C4 1.353(4) . ? N2 C14 1.466(4) . ? N2 C16 1.472(4) . ? C1 C7 1.410(4) . ? C1 C6 1.414(4) . ? C1 C2 1.427(4) . ? C2 C3 1.369(4) . ? C3 C4 1.406(4) . ? C4 C5 1.422(4) . ? C5 C6 1.354(4) . ? C7 C8 1.374(4) . ? C8 C9 1.437(4) . ? C9 C10 1.362(4) . ? C9 C12 1.499(4) . ? C10 C11 1.408(4) . ? C11 C13 1.487(5) . ? C14 C15 1.509(5) . ? C16 C17 1.502(6) . ? 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 B F2 108.7(3) . . ? F1 B O 109.0(3) . . ? F2 B O 109.8(2) . . ? F1 B N1 110.8(2) . . ? F2 B N1 106.2(2) . . ? O B N1 112.2(2) . . ? C2 O B 126.2(2) . . ? C11 N1 C8 107.3(2) . . ? C11 N1 B 128.4(2) . . ? C8 N1 B 123.4(2) . . ? C4 N2 C14 121.6(2) . . ? C4 N2 C16 122.5(3) . . ? C14 N2 C16 115.9(3) . . ? C7 C1 C6 118.9(3) . . ? C7 C1 C2 125.6(3) . . ? C6 C1 C2 115.5(3) . . ? O C2 C3 116.7(2) . . ? O C2 C1 122.1(2) . . ? C3 C2 C1 120.9(3) . . ? C2 C3 C4 122.6(3) . . ? N2 C4 C3 121.5(3) . . ? N2 C4 C5 122.0(3) . . ? C3 C4 C5 116.6(3) . . ? C6 C5 C4 120.6(3) . . ? C5 C6 C1 123.7(3) . . ? C8 C7 C1 133.8(3) . . ? C7 C8 N1 126.9(3) . . ? C7 C8 C9 125.4(3) . . ? N1 C8 C9 107.7(2) . . ? C10 C9 C8 106.5(3) . . ? C10 C9 C12 127.8(3) . . ? C8 C9 C12 125.7(3) . . ? C9 C10 C11 108.6(3) . . ? N1 C11 C10 109.8(3) . . ? N1 C11 C13 124.5(3) . . ? C10 C11 C13 125.7(3) . . ? N2 C14 C15 113.1(3) . . ? N2 C16 C17 112.5(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.30 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.688 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.045 data_c2c _database_code_depnum_ccdc_archive 'CCDC 830331' #TrackingRef 'KAIST(Dhiraj)_end.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H24 B F2 N2 O S' _chemical_formula_weight 413.30 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c 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 20.366(9) _cell_length_b 7.556(3) _cell_length_c 27.882(12) _cell_angle_alpha 90.00 _cell_angle_beta 106.43(3) _cell_angle_gamma 90.00 _cell_volume 4115(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1464 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 19.4945 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1736 _exptl_absorpt_coefficient_mu 0.191 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9535 _exptl_absorpt_correction_T_max 0.9771 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15529 _diffrn_reflns_av_R_equivalents 0.1113 _diffrn_reflns_av_sigmaI/netI 0.1433 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 28.36 _reflns_number_total 5067 _reflns_number_gt 1795 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART APEXll' _computing_cell_refinement 'Bruker SMART APEXll' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SHELXTL _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics WingX _computing_publication_material WingX _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^)+(0.1058P)^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 5067 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2096 _refine_ls_R_factor_gt 0.0802 _refine_ls_wR_factor_ref 0.2490 _refine_ls_wR_factor_gt 0.1924 _refine_ls_goodness_of_fit_ref 0.912 _refine_ls_restrained_S_all 0.912 _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 S1 S 1.00571(7) -0.0674(2) 1.09173(5) 0.0873(5) Uani 1 1 d . . . O1 O 0.75398(14) -0.1049(4) 0.87411(9) 0.0558(8) Uani 1 1 d . . . C1 C 0.6563(2) 0.0457(6) 0.75134(14) 0.0493(11) Uani 1 1 d . . . C3 C 0.7041(2) -0.0222(6) 0.83937(14) 0.0491(10) Uani 1 1 d . . . C4 C 0.6510(2) 0.0687(6) 0.85208(14) 0.0505(11) Uani 1 1 d . . . C2 C 0.7060(2) -0.0349(6) 0.79085(13) 0.0489(10) Uani 1 1 d . . . H2 H 0.7412 -0.0987 0.7838 0.059 Uiso 1 1 calc R . . C5 C 0.6004(2) 0.1435(6) 0.81157(15) 0.0587(12) Uani 1 1 d . . . H5 H 0.5638 0.2014 0.8184 0.070 Uiso 1 1 calc R . . C21 C 0.7775(2) -0.0057(7) 0.69304(18) 0.0716(14) Uani 1 1 d . . . H21A H 0.7721 0.1048 0.6753 0.107 Uiso 1 1 calc R . . H21B H 0.8033 -0.0860 0.6787 0.107 Uiso 1 1 calc R . . H21C H 0.8014 0.0139 0.7276 0.107 Uiso 1 1 calc R . . C6 C 0.6021(2) 0.1359(6) 0.76295(15) 0.0555(12) Uani 1 1 d . . . H6 H 0.5679 0.1895 0.7378 0.067 Uiso 1 1 calc R . . C20 C 0.7080(2) -0.0840(6) 0.68904(15) 0.0559(12) Uani 1 1 d . . . H20A H 0.6877 -0.1214 0.6548 0.067 Uiso 1 1 calc R . . H20B H 0.7141 -0.1888 0.7099 0.067 Uiso 1 1 calc R . . C18 C 0.6212(2) 0.1519(7) 0.66410(15) 0.0638(13) Uani 1 1 d . . . H18A H 0.6502 0.1888 0.6437 0.077 Uiso 1 1 calc R . . H18B H 0.6086 0.2569 0.6795 0.077 Uiso 1 1 calc R . . N1 N 0.66014(17) 0.0339(5) 0.70341(11) 0.0556(10) Uani 1 1 d . . . N2 N 0.75404(17) -0.0078(5) 0.95887(11) 0.0490(9) Uani 1 1 d . . . C7 C 0.6424(2) 0.0768(6) 0.90035(14) 0.0526(11) Uani 1 1 d . . . H7 H 0.5994 0.1170 0.9009 0.063 Uiso 1 1 calc R . . C11 C 0.7766(2) -0.0255(6) 1.00881(14) 0.0522(11) Uani 1 1 d . . . C8 C 0.6845(2) 0.0373(6) 0.94638(14) 0.0510(11) Uani 1 1 d . . . C12 C 0.8471(2) -0.0555(6) 1.03600(14) 0.0554(11) Uani 1 1 d . . . H12 H 0.8796 -0.0541 1.0183 0.066 Uiso 1 1 calc R . . C10 C 0.7217(2) 0.0026(6) 1.02944(15) 0.0604(13) Uani 1 1 d . . . H10 H 0.7243 -0.0042 1.0632 0.073 Uiso 1 1 calc R . . C9 C 0.6648(2) 0.0409(6) 0.99226(15) 0.0599(12) Uani 1 1 d . . . B1 B 0.7956(3) -0.0175(8) 0.91873(17) 0.0557(13) Uani 1 1 d . . . F1 F 0.81182(12) 0.1520(4) 0.90834(8) 0.0699(8) Uani 1 1 d . . . F2 F 0.85325(12) -0.1189(4) 0.93694(8) 0.0719(8) Uani 1 1 d . . . C14 C 0.9377(2) -0.1011(6) 1.11515(15) 0.0587(12) Uani 1 1 d . . . C13 C 0.8683(2) -0.0851(6) 1.08492(15) 0.0612(12) Uani 1 1 d . . . H13 H 0.8345 -0.0967 1.1012 0.073 Uiso 1 1 calc R . . C15 C 0.9590(2) -0.1425(6) 1.16937(15) 0.0576(12) Uani 1 1 d . . . H15A H 0.9410 -0.0555 1.1879 0.069 Uiso 1 1 calc R . . H15B H 0.9429 -0.2588 1.1755 0.069 Uiso 1 1 calc R . . C17 C 1.0620(3) -0.0996(7) 1.14774(19) 0.0761(15) Uani 1 1 d . . . H17 H 1.1091 -0.0920 1.1533 0.091 Uiso 1 1 calc R . . C16 C 1.0325(3) -0.1373(8) 1.18385(19) 0.0880(17) Uani 1 1 d . . . H16 H 1.0584 -0.1591 1.2166 0.106 Uiso 1 1 calc R . . C19 C 0.5571(3) 0.0683(7) 0.63075(17) 0.0833(17) Uani 1 1 d . . . H19A H 0.5693 -0.0302 0.6133 0.125 Uiso 1 1 calc R . . H19B H 0.5325 0.1541 0.6070 0.125 Uiso 1 1 calc R . . H19C H 0.5287 0.0278 0.6508 0.125 Uiso 1 1 calc R . . C22 C 0.5949(2) 0.0796(8) 0.99702(17) 0.0801(16) Uani 1 1 d . . . H22A H 0.5659 -0.0214 0.9862 0.120 Uiso 1 1 calc R . . H22B H 0.5760 0.1798 0.9766 0.120 Uiso 1 1 calc R . . H22C H 0.5980 0.1052 1.0313 0.120 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 S1 0.0822(10) 0.0974(12) 0.0824(10) 0.0070(8) 0.0237(8) 0.0019(8) O1 0.0645(19) 0.068(2) 0.0350(15) -0.0028(14) 0.0140(14) 0.0112(16) C1 0.055(3) 0.060(3) 0.035(2) -0.0028(19) 0.0171(19) -0.004(2) C3 0.053(3) 0.055(3) 0.040(2) 0.002(2) 0.013(2) 0.001(2) C4 0.050(2) 0.063(3) 0.039(2) 0.001(2) 0.014(2) -0.003(2) C2 0.052(2) 0.061(3) 0.037(2) -0.002(2) 0.0199(19) 0.001(2) C5 0.046(2) 0.081(3) 0.054(3) -0.004(2) 0.021(2) 0.003(2) C21 0.078(3) 0.067(3) 0.081(3) 0.009(3) 0.040(3) 0.013(3) C6 0.050(3) 0.070(3) 0.045(2) 0.000(2) 0.011(2) 0.000(2) C20 0.075(3) 0.052(3) 0.043(2) -0.005(2) 0.020(2) 0.000(2) C18 0.064(3) 0.084(3) 0.044(3) 0.010(2) 0.016(2) 0.010(3) N1 0.064(2) 0.068(3) 0.0331(18) 0.0033(17) 0.0119(16) 0.013(2) N2 0.053(2) 0.064(2) 0.0339(18) 0.0033(16) 0.0188(15) 0.0009(19) C7 0.046(2) 0.071(3) 0.044(2) -0.001(2) 0.018(2) 0.000(2) C11 0.065(3) 0.059(3) 0.036(2) 0.003(2) 0.019(2) 0.003(2) C8 0.048(2) 0.066(3) 0.044(2) -0.003(2) 0.020(2) 0.001(2) C12 0.062(3) 0.067(3) 0.043(2) -0.002(2) 0.022(2) -0.001(2) C10 0.066(3) 0.084(4) 0.037(2) -0.001(2) 0.024(2) 0.002(3) C9 0.056(3) 0.081(3) 0.047(3) -0.002(2) 0.023(2) -0.002(2) B1 0.061(3) 0.074(4) 0.037(3) 0.007(3) 0.022(2) 0.006(3) F1 0.0800(18) 0.086(2) 0.0510(15) 0.0002(13) 0.0306(13) -0.0177(15) F2 0.0586(16) 0.115(2) 0.0429(14) 0.0059(14) 0.0152(12) 0.0264(16) C14 0.059(3) 0.072(3) 0.048(3) -0.004(2) 0.020(2) 0.008(2) C13 0.065(3) 0.082(4) 0.039(2) 0.000(2) 0.018(2) 0.001(3) C15 0.046(3) 0.066(3) 0.053(3) -0.008(2) 0.001(2) 0.005(2) C17 0.060(3) 0.078(4) 0.082(4) -0.008(3) 0.006(3) 0.003(3) C16 0.099(4) 0.108(5) 0.051(3) -0.009(3) 0.012(3) 0.005(4) C19 0.082(4) 0.095(4) 0.057(3) 0.006(3) -0.006(3) 0.005(3) C22 0.068(3) 0.121(5) 0.057(3) -0.004(3) 0.027(3) -0.002(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 S1 C17 1.673(5) . ? S1 C14 1.710(5) . ? O1 C3 1.343(4) . ? O1 B1 1.451(6) . ? C1 N1 1.363(5) . ? C1 C2 1.406(5) . ? C1 C6 1.411(5) . ? C3 C2 1.368(5) . ? C3 C4 1.408(6) . ? C4 C7 1.407(5) . ? C4 C5 1.414(6) . ? C5 C6 1.367(5) . ? C21 C20 1.509(6) . ? C20 N1 1.458(5) . ? C18 N1 1.461(5) . ? C18 C19 1.510(6) . ? N2 C11 1.344(5) . ? N2 C8 1.402(5) . ? N2 B1 1.585(6) . ? C7 C8 1.360(5) . ? C11 C10 1.410(6) . ? C11 C12 1.440(6) . ? C8 C9 1.445(5) . ? C12 C13 1.328(5) . ? C10 C9 1.349(6) . ? C9 C22 1.496(6) . ? B1 F2 1.374(6) . ? B1 F1 1.374(6) . ? C14 C13 1.431(6) . ? C14 C15 1.484(6) . ? C15 C16 1.436(7) . ? C17 C16 1.340(7) . ? 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 S1 C14 92.1(3) . . ? C3 O1 B1 123.0(4) . . ? N1 C1 C2 120.8(4) . . ? N1 C1 C6 121.4(4) . . ? C2 C1 C6 117.8(3) . . ? O1 C3 C2 116.9(4) . . ? O1 C3 C4 121.6(3) . . ? C2 C3 C4 121.4(4) . . ? C7 C4 C3 125.1(4) . . ? C7 C4 C5 119.1(4) . . ? C3 C4 C5 115.6(4) . . ? C3 C2 C1 122.0(4) . . ? C6 C5 C4 123.9(4) . . ? C5 C6 C1 119.3(4) . . ? N1 C20 C21 115.2(4) . . ? N1 C18 C19 113.5(4) . . ? C1 N1 C20 122.5(3) . . ? C1 N1 C18 121.7(4) . . ? C20 N1 C18 115.5(3) . . ? C11 N2 C8 107.9(3) . . ? C11 N2 B1 129.3(4) . . ? C8 N2 B1 122.7(3) . . ? C8 C7 C4 132.6(4) . . ? N2 C11 C10 109.3(4) . . ? N2 C11 C12 124.0(4) . . ? C10 C11 C12 126.6(4) . . ? C7 C8 N2 127.7(3) . . ? C7 C8 C9 124.9(4) . . ? N2 C8 C9 107.4(3) . . ? C13 C12 C11 123.5(4) . . ? C9 C10 C11 109.0(4) . . ? C10 C9 C8 106.5(4) . . ? C10 C9 C22 127.3(4) . . ? C8 C9 C22 126.3(4) . . ? F2 B1 F1 111.5(4) . . ? F2 B1 O1 107.1(4) . . ? F1 B1 O1 111.1(4) . . ? F2 B1 N2 109.6(3) . . ? F1 B1 N2 108.3(4) . . ? O1 B1 N2 109.1(4) . . ? C13 C14 C15 125.0(4) . . ? C13 C14 S1 122.3(3) . . ? C15 C14 S1 112.6(3) . . ? C12 C13 C14 126.8(4) . . ? C16 C15 C14 105.2(4) . . ? C16 C17 S1 113.5(4) . . ? C17 C16 C15 116.5(5) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 28.36 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.264 _refine_diff_density_min -0.426 _refine_diff_density_rms 0.068 data_nchu46-4 _database_code_depnum_ccdc_archive 'CCDC 831215' #TrackingRef 'nchu46-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety C20H22BF2N3 _chemical_formula_sum 'C20 H22 B F2 N3' _chemical_formula_weight 353.22 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 Pbca 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' '-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 12.7459(15) _cell_length_b 12.7700(13) _cell_length_c 23.352(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3800.9(7) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3254 _cell_measurement_theta_min 1.74 _cell_measurement_theta_max 24.80 _exptl_crystal_description platy _exptl_crystal_colour red _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.930 _exptl_absorpt_correction_T_max 0.941 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 22184 _diffrn_reflns_av_R_equivalents 0.1506 _diffrn_reflns_av_sigmaI/netI 0.0803 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 24.80 _reflns_number_total 3254 _reflns_number_gt 1588 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker APEX II' _computing_data_reduction 'Bruker APEX II' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP3 _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^)+(0.0791P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3254 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1461 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1740 _refine_ls_wR_factor_gt 0.1215 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.060 _refine_ls_shift/su_mean 0.001 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 B B 0.1233(3) 0.1038(3) 1.03183(14) 0.0447(10) Uani 1 1 d . . . F1 F 0.06568(17) 0.02742(15) 1.06112(7) 0.0638(6) Uani 1 1 d . . . F2 F 0.16989(16) 0.16888(15) 1.07225(7) 0.0628(6) Uani 1 1 d . . . N1 N 0.2072(2) 0.05156(19) 0.99385(10) 0.0437(7) Uani 1 1 d . . . N2 N 0.0504(2) 0.1667(2) 0.99211(10) 0.0446(7) Uani 1 1 d . . . C1 C 0.2849(3) -0.0128(3) 1.01120(14) 0.0560(10) Uani 1 1 d . . . C2 C 0.3458(3) -0.0408(3) 0.96413(17) 0.0683(11) Uani 1 1 d . . . H2 H 0.4036 -0.0851 0.9649 0.082 Uiso 1 1 calc R . . C3 C 0.3059(3) 0.0082(3) 0.91615(14) 0.0557(10) Uani 1 1 d . . . C4 C 0.2173(3) 0.0661(2) 0.93452(12) 0.0429(8) Uani 1 1 d . . . C5 C 0.1445(3) 0.1273(2) 0.90467(12) 0.0424(8) Uani 1 1 d . . . C6 C 0.0607(3) 0.1754(3) 0.93259(13) 0.0430(8) Uani 1 1 d . . . C7 C -0.0272(3) 0.2335(3) 0.91184(15) 0.0542(10) Uani 1 1 d . . . C8 C -0.0861(3) 0.2583(3) 0.95884(17) 0.0664(11) Uani 1 1 d . . . H8 H -0.1480 0.2968 0.9584 0.080 Uiso 1 1 calc R . . C9 C -0.0382(3) 0.2164(3) 1.00792(15) 0.0575(10) Uani 1 1 d . . . N3 N 0.0438(3) -0.0079(3) 0.82524(15) 0.0849(13) Uani 1 1 d . . . C10 C 0.1555(3) 0.1411(3) 0.84102(13) 0.0529(10) Uani 1 1 d . . . C11 C 0.1032(3) 0.0716(3) 0.80364(14) 0.0640(11) Uani 1 1 d . . . C12 C 0.1169(4) 0.0871(4) 0.74470(15) 0.0852(15) Uani 1 1 d . . . H12 H 0.0846 0.0419 0.7189 0.102 Uiso 1 1 calc R . . C13 C 0.1772(4) 0.1677(4) 0.72451(16) 0.0887(15) Uani 1 1 d . . . H13 H 0.1846 0.1763 0.6852 0.106 Uiso 1 1 calc R . . C14 C 0.2274(4) 0.2368(4) 0.76111(16) 0.0810(13) Uani 1 1 d . . . H14 H 0.2676 0.2917 0.7469 0.097 Uiso 1 1 calc R . . C15 C 0.2158(3) 0.2217(3) 0.81934(13) 0.0622(11) Uani 1 1 d . . . H15 H 0.2495 0.2669 0.8446 0.075 Uiso 1 1 calc R . . C16 C -0.0276(5) -0.0707(4) 0.79118(17) 0.123(2) Uani 1 1 d . . . H16A H -0.0757 -0.0255 0.7714 0.184 Uiso 1 1 calc R . . H16B H -0.0659 -0.1172 0.8158 0.184 Uiso 1 1 calc R . . H16C H 0.0117 -0.1108 0.7638 0.184 Uiso 1 1 calc R . . C17 C 0.3517(4) -0.0009(3) 0.85684(16) 0.0811(13) Uani 1 1 d . . . H17A H 0.4080 -0.0509 0.8572 0.122 Uiso 1 1 calc R . . H17B H 0.3781 0.0660 0.8449 0.122 Uiso 1 1 calc R . . H17C H 0.2983 -0.0237 0.8307 0.122 Uiso 1 1 calc R . . C18 C 0.2993(4) -0.0467(3) 1.07199(16) 0.0810(13) Uani 1 1 d . . . H18A H 0.3003 0.0138 1.0964 0.121 Uiso 1 1 calc R . . H18B H 0.3644 -0.0839 1.0756 0.121 Uiso 1 1 calc R . . H18C H 0.2423 -0.0916 1.0829 0.121 Uiso 1 1 calc R . . C19 C -0.0568(3) 0.2609(3) 0.85147(16) 0.0795(13) Uani 1 1 d . . . H19A H -0.0766 0.1984 0.8313 0.119 Uiso 1 1 calc R . . H19B H 0.0020 0.2928 0.8326 0.119 Uiso 1 1 calc R . . H19C H -0.1147 0.3089 0.8519 0.119 Uiso 1 1 calc R . . C20 C -0.0764(4) 0.2225(4) 1.06801(17) 0.0929(15) Uani 1 1 d . . . H20A H -0.1084 0.1571 1.0784 0.139 Uiso 1 1 calc R . . H20B H -0.1271 0.2778 1.0713 0.139 Uiso 1 1 calc R . . H20C H -0.0185 0.2364 1.0931 0.139 Uiso 1 1 calc R . . H101 H 0.026(3) -0.001(3) 0.8610(17) 0.079(13) Uiso 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 B 0.050(3) 0.047(3) 0.0369(18) -0.0034(18) 0.0039(19) -0.009(2) F1 0.0703(16) 0.0611(14) 0.0599(11) 0.0114(10) 0.0125(10) -0.0115(12) F2 0.0627(15) 0.0728(14) 0.0530(11) -0.0187(10) -0.0005(10) -0.0083(12) N1 0.0452(18) 0.0419(16) 0.0439(15) 0.0015(12) -0.0014(13) 0.0043(15) N2 0.0396(18) 0.0441(18) 0.0502(16) -0.0011(13) 0.0071(13) 0.0013(15) C1 0.062(3) 0.045(2) 0.061(2) 0.0054(18) -0.009(2) 0.006(2) C2 0.062(3) 0.060(3) 0.082(3) -0.003(2) 0.003(2) 0.021(2) C3 0.058(3) 0.050(2) 0.059(2) -0.0106(18) 0.0108(19) 0.006(2) C4 0.048(2) 0.0407(19) 0.0403(17) -0.0059(15) 0.0066(16) -0.0001(19) C5 0.045(2) 0.040(2) 0.0417(17) -0.0040(15) -0.0017(16) -0.0073(18) C6 0.043(2) 0.042(2) 0.0440(18) 0.0008(15) -0.0053(16) -0.0053(18) C7 0.044(2) 0.050(2) 0.068(2) 0.0051(18) -0.0083(19) -0.0053(19) C8 0.046(3) 0.055(3) 0.098(3) 0.010(2) 0.002(2) 0.009(2) C9 0.052(3) 0.049(2) 0.071(2) -0.0018(19) 0.018(2) 0.002(2) N3 0.120(4) 0.087(3) 0.048(2) -0.0134(19) -0.002(2) -0.050(3) C10 0.058(3) 0.059(2) 0.0415(17) -0.0017(16) -0.0008(17) -0.008(2) C11 0.078(3) 0.070(3) 0.044(2) -0.0017(19) 0.001(2) -0.013(2) C12 0.108(4) 0.102(4) 0.045(2) -0.009(2) 0.001(2) -0.027(3) C13 0.111(4) 0.113(4) 0.041(2) 0.004(2) 0.010(2) -0.017(3) C14 0.090(3) 0.095(3) 0.057(2) 0.016(2) 0.007(2) -0.016(3) C15 0.070(3) 0.067(3) 0.050(2) 0.0071(18) -0.0010(18) -0.011(2) C16 0.159(6) 0.142(5) 0.068(3) -0.021(3) -0.013(3) -0.084(4) C17 0.082(3) 0.079(3) 0.082(3) -0.017(2) 0.026(2) 0.015(3) C18 0.086(3) 0.079(3) 0.078(3) 0.020(2) -0.016(2) 0.018(3) C19 0.070(3) 0.081(3) 0.087(3) 0.011(2) -0.031(2) 0.001(3) C20 0.094(4) 0.091(4) 0.093(3) 0.003(3) 0.044(3) 0.022(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 B F2 1.391(4) . ? B F1 1.399(4) . ? B N2 1.539(5) . ? B N1 1.541(5) . ? N1 C1 1.349(4) . ? N1 C4 1.404(4) . ? N2 C9 1.347(4) . ? N2 C6 1.401(4) . ? C1 C2 1.392(5) . ? C1 C18 1.495(5) . ? C2 C3 1.381(5) . ? C3 C4 1.416(5) . ? C3 C17 1.508(5) . ? C4 C5 1.399(4) . ? C5 C6 1.394(4) . ? C5 C10 1.503(4) . ? C6 C7 1.428(5) . ? C7 C8 1.367(5) . ? C7 C19 1.501(5) . ? C8 C9 1.404(5) . ? C9 C20 1.488(5) . ? N3 C11 1.363(5) . ? N3 C16 1.450(5) . ? C10 C15 1.381(5) . ? C10 C11 1.412(5) . ? C11 C12 1.401(5) . ? C12 C13 1.368(6) . ? C13 C14 1.385(6) . ? C14 C15 1.381(5) . ? 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 F2 B F1 108.0(3) . . ? F2 B N2 110.8(3) . . ? F1 B N2 110.0(3) . . ? F2 B N1 110.6(3) . . ? F1 B N1 110.1(3) . . ? N2 B N1 107.4(2) . . ? C1 N1 C4 108.1(3) . . ? C1 N1 B 126.9(3) . . ? C4 N1 B 125.0(3) . . ? C9 N2 C6 108.3(3) . . ? C9 N2 B 126.0(3) . . ? C6 N2 B 125.6(3) . . ? N1 C1 C2 109.2(3) . . ? N1 C1 C18 123.4(3) . . ? C2 C1 C18 127.4(4) . . ? C3 C2 C1 108.6(3) . . ? C2 C3 C4 106.5(3) . . ? C2 C3 C17 124.6(4) . . ? C4 C3 C17 128.9(3) . . ? C5 C4 N1 120.3(3) . . ? C5 C4 C3 132.0(3) . . ? N1 C4 C3 107.6(3) . . ? C6 C5 C4 121.4(3) . . ? C6 C5 C10 118.8(3) . . ? C4 C5 C10 119.8(3) . . ? C5 C6 N2 120.1(3) . . ? C5 C6 C7 132.2(3) . . ? N2 C6 C7 107.7(3) . . ? C8 C7 C6 106.2(3) . . ? C8 C7 C19 124.2(4) . . ? C6 C7 C19 129.6(3) . . ? C7 C8 C9 109.2(3) . . ? N2 C9 C8 108.7(3) . . ? N2 C9 C20 123.9(4) . . ? C8 C9 C20 127.4(4) . . ? C11 N3 C16 123.8(4) . . ? C15 C10 C11 120.3(3) . . ? C15 C10 C5 120.1(3) . . ? C11 C10 C5 119.6(3) . . ? N3 C11 C12 122.5(4) . . ? N3 C11 C10 120.1(3) . . ? C12 C11 C10 117.3(4) . . ? C13 C12 C11 121.0(4) . . ? C12 C13 C14 121.8(4) . . ? C15 C14 C13 118.0(4) . . ? C10 C15 C14 121.6(4) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.80 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.251 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.103