# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012 data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email dchurchill@kaist.ac.kr _publ_contact_author_name 'David G. Churchill' loop_ _publ_author_name 'Olga G. Tsay ' 'Kang Mun Lee' 'David G. Churchill' data_nchu83-1 _database_code_depnum_ccdc_archive 'CCDC 875567' #TrackingRef '10594_web_deposit_cif_file_0_OlgaTsay_1333952940.nchu83-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety C20H19B1F2N2O2 _chemical_formula_sum 'C20 H19 B F2 N2 O2' _chemical_formula_weight 368.18 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 11.408(3) _cell_length_b 8.848(2) _cell_length_c 18.193(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.562(11) _cell_angle_gamma 90.00 _cell_volume 1820.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2572 _cell_measurement_theta_min 1.80 _cell_measurement_theta_max 23.22 _exptl_crystal_description Cubic _exptl_crystal_colour Red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.100 _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 19941 _diffrn_reflns_av_R_equivalents 0.0685 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 23.22 _reflns_number_total 2572 _reflns_number_gt 1957 _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^)+(0.0585P)^2^+0.6338P] 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 2572 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0691 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1272 _refine_ls_wR_factor_gt 0.1167 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 B B 0.8892(3) 0.0863(4) 0.36434(17) 0.0488(8) Uani 1 1 d . . . C20 C 0.9347(3) 0.2603(4) 0.51250(16) 0.0802(10) Uani 1 1 d . . . H20A H 0.8965 0.1709 0.5275 0.120 Uiso 1 1 calc R . . H20B H 0.9400 0.3338 0.5516 0.120 Uiso 1 1 calc R . . H20C H 1.0127 0.2353 0.5021 0.120 Uiso 1 1 calc R . . F1 F 1.01340(13) 0.0871(2) 0.37513(8) 0.0683(5) Uani 1 1 d . . . F2 F 0.84913(15) -0.01914(18) 0.41110(8) 0.0667(5) Uani 1 1 d . . . N1 N 0.84302(18) 0.0504(2) 0.28258(11) 0.0469(6) Uani 1 1 d . . . N2 N 0.84226(19) 0.2468(2) 0.38008(11) 0.0486(6) Uani 1 1 d . . . O1 O 0.4359(2) 0.6607(3) 0.06183(13) 0.0858(7) Uani 1 1 d . . . H1 H 0.4731 0.7007 0.0315 0.129 Uiso 1 1 calc R . . O2 O 0.6254(2) 0.7229(3) -0.00164(12) 0.0891(8) Uani 1 1 d . . . C1 C 0.8634(2) -0.0791(3) 0.24625(15) 0.0539(7) Uani 1 1 d . . . C2 C 0.7986(3) -0.0748(3) 0.17529(16) 0.0614(8) Uani 1 1 d . . . H2 H 0.7978 -0.1502 0.1396 0.074 Uiso 1 1 calc R . . C3 C 0.7362(2) 0.0593(3) 0.16673(14) 0.0528(7) Uani 1 1 d . . . C4 C 0.7654(2) 0.1403(3) 0.23426(13) 0.0443(6) Uani 1 1 d . . . C5 C 0.7327(2) 0.2842(3) 0.25753(13) 0.0432(6) Uani 1 1 d . . . C6 C 0.7715(2) 0.3376(3) 0.32871(13) 0.0454(7) Uani 1 1 d . . . C7 C 0.7519(2) 0.4784(3) 0.36478(14) 0.0517(7) Uani 1 1 d . . . C8 C 0.8098(3) 0.4655(3) 0.43567(15) 0.0621(8) Uani 1 1 d . . . H8 H 0.8122 0.5395 0.4722 0.075 Uiso 1 1 calc R . . C9 C 0.8645(3) 0.3241(3) 0.44439(14) 0.0576(8) Uani 1 1 d . . . C10 C 0.6554(2) 0.3826(3) 0.20446(13) 0.0447(7) Uani 1 1 d . . . C11 C 0.7011(2) 0.4596(3) 0.14878(14) 0.0508(7) Uani 1 1 d . . . H11 H 0.7807 0.4485 0.1438 0.061 Uiso 1 1 calc R . . C12 C 0.6297(3) 0.5548(3) 0.09913(14) 0.0512(7) Uani 1 1 d . . . C13 C 0.5098(3) 0.5702(3) 0.10771(15) 0.0565(8) Uani 1 1 d . . . C14 C 0.4627(3) 0.4911(3) 0.16221(16) 0.0609(8) Uani 1 1 d . . . H14 H 0.3827 0.4993 0.1667 0.073 Uiso 1 1 calc R . . C15 C 0.5350(2) 0.3997(3) 0.20999(14) 0.0531(7) Uani 1 1 d . . . H15 H 0.5027 0.3478 0.2470 0.064 Uiso 1 1 calc R . . C16 C 0.6802(3) 0.6323(4) 0.04094(16) 0.0682(9) Uani 1 1 d . . . H16 H 0.7587 0.6126 0.0354 0.082 Uiso 1 1 calc R . . C17 C 0.6515(3) 0.1016(4) 0.09851(15) 0.0693(9) Uani 1 1 d . . . H17A H 0.6880 0.1753 0.0701 0.104 Uiso 1 1 calc R . . H17B H 0.5805 0.1432 0.1134 0.104 Uiso 1 1 calc R . . H17C H 0.6323 0.0132 0.0688 0.104 Uiso 1 1 calc R . . C18 C 0.9438(3) -0.2016(4) 0.27996(18) 0.0739(9) Uani 1 1 d . . . H18A H 1.0245 -0.1695 0.2820 0.111 Uiso 1 1 calc R . . H18B H 0.9316 -0.2914 0.2503 0.111 Uiso 1 1 calc R . . H18C H 0.9267 -0.2226 0.3292 0.111 Uiso 1 1 calc R . . C19 C 0.6831(3) 0.6145(3) 0.33468(17) 0.0672(9) Uani 1 1 d . . . H19A H 0.6000 0.5931 0.3307 0.101 Uiso 1 1 calc R . . H19B H 0.7037 0.6389 0.2866 0.101 Uiso 1 1 calc R . . H19C H 0.7015 0.6986 0.3675 0.101 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 0.045(2) 0.0538(19) 0.0477(18) 0.0080(15) 0.0052(15) 0.0061(15) C20 0.095(3) 0.089(2) 0.0517(18) -0.0005(17) -0.0107(17) 0.009(2) F1 0.0483(10) 0.0872(12) 0.0667(11) -0.0029(9) -0.0023(8) 0.0126(9) F2 0.0823(12) 0.0603(10) 0.0590(10) 0.0167(8) 0.0151(9) 0.0070(9) N1 0.0456(13) 0.0457(13) 0.0501(13) 0.0005(11) 0.0091(10) 0.0047(11) N2 0.0517(14) 0.0537(14) 0.0395(12) 0.0026(10) 0.0033(10) 0.0039(11) O1 0.0866(17) 0.0837(17) 0.0814(17) 0.0203(13) -0.0105(12) 0.0243(14) O2 0.125(2) 0.0743(15) 0.0634(14) 0.0238(12) -0.0043(13) 0.0014(15) C1 0.0505(17) 0.0524(18) 0.0597(18) -0.0026(14) 0.0101(14) 0.0058(14) C2 0.068(2) 0.0561(19) 0.0587(19) -0.0144(15) 0.0048(15) 0.0043(16) C3 0.0555(18) 0.0553(18) 0.0470(16) -0.0011(13) 0.0040(13) -0.0001(14) C4 0.0436(16) 0.0472(16) 0.0425(15) 0.0013(12) 0.0066(12) 0.0026(13) C5 0.0408(15) 0.0498(16) 0.0404(14) 0.0045(12) 0.0104(12) 0.0000(13) C6 0.0456(16) 0.0508(16) 0.0398(15) 0.0053(12) 0.0052(12) 0.0046(13) C7 0.0565(18) 0.0512(17) 0.0481(16) -0.0007(13) 0.0099(14) 0.0054(14) C8 0.082(2) 0.0569(19) 0.0475(17) -0.0093(14) 0.0083(16) 0.0027(16) C9 0.066(2) 0.067(2) 0.0389(16) -0.0027(14) 0.0019(13) 0.0011(16) C10 0.0468(17) 0.0460(16) 0.0404(15) -0.0015(12) 0.0023(12) 0.0025(13) C11 0.0519(17) 0.0536(17) 0.0459(15) -0.0019(13) 0.0026(13) 0.0013(14) C12 0.062(2) 0.0473(16) 0.0430(15) -0.0008(13) 0.0005(14) -0.0018(14) C13 0.063(2) 0.0531(17) 0.0503(17) -0.0011(14) -0.0053(14) 0.0057(15) C14 0.0480(17) 0.067(2) 0.0669(19) -0.0015(16) 0.0041(15) 0.0073(15) C15 0.0476(18) 0.0582(18) 0.0532(17) 0.0016(14) 0.0053(13) 0.0038(14) C16 0.089(2) 0.061(2) 0.0531(18) 0.0061(16) 0.0037(17) -0.0076(17) C17 0.078(2) 0.073(2) 0.0534(18) -0.0094(16) -0.0061(16) 0.0008(17) C18 0.070(2) 0.063(2) 0.086(2) -0.0081(17) 0.0021(17) 0.0210(17) C19 0.081(2) 0.0551(19) 0.0655(19) -0.0027(15) 0.0107(16) 0.0125(16) _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 1.380(3) . ? B F1 1.404(3) . ? B N1 1.544(4) . ? B N2 1.558(4) . ? C20 C9 1.495(4) . ? N1 C1 1.358(3) . ? N1 C4 1.409(3) . ? N2 C9 1.350(3) . ? N2 C6 1.404(3) . ? O1 C13 1.365(3) . ? O2 C16 1.227(3) . ? C1 C2 1.401(4) . ? C1 C18 1.498(4) . ? C2 C3 1.382(4) . ? C3 C4 1.423(3) . ? C3 C17 1.516(4) . ? C4 C5 1.407(4) . ? C5 C6 1.395(3) . ? C5 C10 1.498(3) . ? C6 C7 1.440(4) . ? C7 C8 1.374(4) . ? C7 C19 1.501(4) . ? C8 C9 1.398(4) . ? C10 C11 1.379(4) . ? C10 C15 1.399(4) . ? C11 C12 1.412(4) . ? C12 C13 1.405(4) . ? C12 C16 1.444(4) . ? C13 C14 1.379(4) . ? C14 C15 1.379(4) . ? 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 109.1(2) . . ? F2 B N1 110.8(2) . . ? F1 B N1 110.2(2) . . ? F2 B N2 110.7(2) . . ? F1 B N2 109.5(2) . . ? N1 B N2 106.4(2) . . ? C1 N1 C4 107.9(2) . . ? C1 N1 B 125.7(2) . . ? C4 N1 B 126.3(2) . . ? C9 N2 C6 108.3(2) . . ? C9 N2 B 126.2(2) . . ? C6 N2 B 125.5(2) . . ? N1 C1 C2 108.8(2) . . ? N1 C1 C18 123.1(2) . . ? C2 C1 C18 128.1(3) . . ? C3 C2 C1 109.2(3) . . ? C2 C3 C4 106.0(2) . . ? C2 C3 C17 124.6(3) . . ? C4 C3 C17 129.3(3) . . ? C5 C4 N1 119.5(2) . . ? C5 C4 C3 132.4(2) . . ? N1 C4 C3 108.1(2) . . ? C6 C5 C4 121.4(2) . . ? C6 C5 C10 119.3(2) . . ? C4 C5 C10 119.3(2) . . ? C5 C6 N2 120.6(2) . . ? C5 C6 C7 131.8(2) . . ? N2 C6 C7 107.6(2) . . ? C8 C7 C6 105.8(2) . . ? C8 C7 C19 124.9(3) . . ? C6 C7 C19 129.3(2) . . ? C7 C8 C9 109.4(2) . . ? N2 C9 C8 109.0(2) . . ? N2 C9 C20 123.1(3) . . ? C8 C9 C20 127.9(3) . . ? C11 C10 C15 118.0(2) . . ? C11 C10 C5 120.9(2) . . ? C15 C10 C5 121.1(2) . . ? C10 C11 C12 121.6(3) . . ? C13 C12 C11 118.3(2) . . ? C13 C12 C16 121.6(3) . . ? C11 C12 C16 120.1(3) . . ? O1 C13 C14 118.0(3) . . ? O1 C13 C12 121.4(3) . . ? C14 C13 C12 120.5(3) . . ? C15 C14 C13 119.6(3) . . ? C14 C15 C10 122.0(3) . . ? O2 C16 C12 123.6(3) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 23.22 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.201 _refine_diff_density_min -0.118 _refine_diff_density_rms 0.036 data_nchu81-1 _database_code_depnum_ccdc_archive 'CCDC 881381' #TrackingRef '11193_web_deposit_cif_file_0_OlgaG.Tsay_1336611135.nchu81-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety C23H25B1F2N2O2 _chemical_formula_sum 'C23 H25 B F2 N2 O2' _chemical_formula_weight 410.26 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)/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 13.996(2) _cell_length_b 11.0508(17) _cell_length_c 14.095(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.373(7) _cell_angle_gamma 90.00 _cell_volume 2144.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2935 _cell_measurement_theta_min 1.89 _cell_measurement_theta_max 23.10 _exptl_crystal_description Cubic _exptl_crystal_colour Darkred _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.092 _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 23730 _diffrn_reflns_av_R_equivalents 0.0633 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 23.10 _reflns_number_total 2935 _reflns_number_gt 2372 _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^)+(0.1021P)^2^+3.9475P] 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 2935 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1000 _refine_ls_R_factor_gt 0.0844 _refine_ls_wR_factor_ref 0.2299 _refine_ls_wR_factor_gt 0.2186 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.002 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 0.3028(4) 0.1222(5) 0.4292(4) 0.0488(13) Uani 1 1 d . . . F1 F 0.2196(2) 0.0516(3) 0.4148(2) 0.0783(10) Uani 1 1 d . . . F2 F 0.3615(2) 0.0888(3) 0.36389(19) 0.0757(10) Uani 1 1 d . . . N1 N 0.3592(3) 0.1063(3) 0.5337(2) 0.0416(9) Uani 1 1 d . . . N2 N 0.2763(3) 0.2575(3) 0.4159(2) 0.0442(9) Uani 1 1 d . . . O1 O 0.3933(3) 0.6880(3) 0.8652(3) 0.0774(11) Uani 1 1 d . . . O2 O 0.5292(3) 0.7584(3) 0.8098(2) 0.0730(11) Uani 1 1 d . . . C1 C 0.3970(3) 0.0019(4) 0.5748(3) 0.0477(11) Uani 1 1 d . . . C2 C 0.4402(3) 0.0240(4) 0.6709(3) 0.0520(12) Uani 1 1 d . . . H2 H 0.4721 -0.0328 0.7140 0.062 Uiso 1 1 calc R . . C3 C 0.4271(3) 0.1441(4) 0.6905(3) 0.0506(12) Uani 1 1 d . . . C4 C 0.3773(3) 0.1978(4) 0.6038(3) 0.0426(10) Uani 1 1 d . . . C5 C 0.3472(3) 0.3171(4) 0.5798(3) 0.0447(11) Uani 1 1 d . . . C6 C 0.2973(3) 0.3471(4) 0.4874(3) 0.0443(11) Uani 1 1 d . . . C7 C 0.2593(3) 0.4590(4) 0.4467(3) 0.0555(12) Uani 1 1 d . . . C8 C 0.2173(4) 0.4338(4) 0.3523(4) 0.0599(13) Uani 1 1 d . . . H8 H 0.1865 0.4897 0.3077 0.072 Uiso 1 1 calc R . . C9 C 0.2288(3) 0.3112(4) 0.3351(3) 0.0523(12) Uani 1 1 d . . . C10 C 0.3651(4) 0.4137(4) 0.6567(3) 0.0566(13) Uani 1 1 d . . . C11 C 0.2961(4) 0.4307(5) 0.7179(4) 0.0703(15) Uani 1 1 d . . . H11 H 0.2420 0.3805 0.7115 0.084 Uiso 1 1 calc R . . C12 C 0.3082(4) 0.5208(6) 0.7871(4) 0.0758(17) Uani 1 1 d . . . H12 H 0.2630 0.5329 0.8271 0.091 Uiso 1 1 calc R . . C13 C 0.3880(3) 0.5901(5) 0.7942(4) 0.0585(13) Uani 1 1 d . . . C14 C 0.4595(3) 0.5809(5) 0.7409(3) 0.0561(12) Uani 1 1 d . . . C15 C 0.4446(4) 0.4832(5) 0.6689(4) 0.0633(14) Uani 1 1 d . . . H15 H 0.4915 0.4695 0.6310 0.076 Uiso 1 1 calc R . . C16 C 0.5467(4) 0.6550(5) 0.7560(4) 0.0755(16) Uani 1 1 d . . . H16A H 0.6011 0.6094 0.7909 0.091 Uiso 1 1 calc R . . H16B H 0.5623 0.6794 0.6945 0.091 Uiso 1 1 calc R . . C17 C 0.4882(4) 0.7371(4) 0.8935(3) 0.0602(13) Uani 1 1 d . . . C18 C 0.5490(5) 0.6516(5) 0.9631(4) 0.0813(18) Uani 1 1 d . . . H18A H 0.5188 0.6400 1.0184 0.122 Uiso 1 1 calc R . . H18B H 0.6126 0.6852 0.9832 0.122 Uiso 1 1 calc R . . H18C H 0.5541 0.5752 0.9320 0.122 Uiso 1 1 calc R . . C19 C 0.4753(4) 0.8599(5) 0.9339(4) 0.0732(16) Uani 1 1 d . . . H19A H 0.4392 0.9102 0.8845 0.110 Uiso 1 1 calc R . . H19B H 0.5378 0.8955 0.9566 0.110 Uiso 1 1 calc R . . H19C H 0.4406 0.8528 0.9865 0.110 Uiso 1 1 calc R . . C20 C 0.4558(4) 0.2010(5) 0.7891(3) 0.0701(15) Uani 1 1 d . . . H20A H 0.3984 0.2232 0.8134 0.105 Uiso 1 1 calc R . . H20B H 0.4943 0.2719 0.7842 0.105 Uiso 1 1 calc R . . H20C H 0.4929 0.1441 0.8322 0.105 Uiso 1 1 calc R . . C21 C 0.3921(4) -0.1160(4) 0.5230(4) 0.0662(14) Uani 1 1 d . . . H21A H 0.3254 -0.1367 0.4996 0.099 Uiso 1 1 calc R . . H21B H 0.4219 -0.1778 0.5664 0.099 Uiso 1 1 calc R . . H21C H 0.4259 -0.1096 0.4696 0.099 Uiso 1 1 calc R . . C22 C 0.2623(5) 0.5810(4) 0.4919(4) 0.0805(18) Uani 1 1 d . . . H22A H 0.3287 0.6050 0.5128 0.121 Uiso 1 1 calc R . . H22B H 0.2300 0.5783 0.5464 0.121 Uiso 1 1 calc R . . H22C H 0.2303 0.6383 0.4457 0.121 Uiso 1 1 calc R . . C23 C 0.1988(4) 0.2430(5) 0.2419(4) 0.0727(16) Uani 1 1 d . . . H23A H 0.2550 0.2272 0.2135 0.109 Uiso 1 1 calc R . . H23B H 0.1532 0.2906 0.1982 0.109 Uiso 1 1 calc R . . H23C H 0.1691 0.1677 0.2545 0.109 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 0.056(3) 0.044(3) 0.045(3) -0.010(2) 0.007(2) -0.002(3) F1 0.077(2) 0.0578(18) 0.089(2) 0.0009(15) -0.0158(16) -0.0269(15) F2 0.099(2) 0.084(2) 0.0457(16) -0.0080(14) 0.0174(15) 0.0297(18) N1 0.052(2) 0.0317(19) 0.0416(19) -0.0016(16) 0.0097(16) -0.0023(16) N2 0.050(2) 0.044(2) 0.038(2) -0.0028(16) 0.0044(16) -0.0038(17) O1 0.092(3) 0.071(2) 0.067(2) -0.0221(19) 0.011(2) -0.020(2) O2 0.105(3) 0.055(2) 0.060(2) -0.0078(17) 0.018(2) 0.012(2) C1 0.054(3) 0.040(3) 0.051(3) 0.002(2) 0.015(2) -0.003(2) C2 0.058(3) 0.048(3) 0.051(3) 0.011(2) 0.012(2) 0.010(2) C3 0.052(3) 0.055(3) 0.043(3) -0.003(2) 0.006(2) 0.005(2) C4 0.048(2) 0.042(2) 0.038(2) -0.0037(19) 0.0052(19) 0.002(2) C5 0.048(2) 0.042(3) 0.043(2) -0.007(2) 0.005(2) 0.000(2) C6 0.049(3) 0.036(2) 0.046(2) -0.002(2) 0.005(2) -0.0042(19) C7 0.058(3) 0.043(3) 0.062(3) 0.005(2) 0.001(2) 0.001(2) C8 0.071(3) 0.051(3) 0.055(3) 0.014(2) 0.007(2) 0.005(2) C9 0.059(3) 0.056(3) 0.039(3) 0.004(2) 0.002(2) -0.004(2) C10 0.061(3) 0.043(3) 0.059(3) -0.004(2) -0.009(2) 0.006(2) C11 0.076(4) 0.067(4) 0.067(3) -0.025(3) 0.011(3) 0.002(3) C12 0.062(3) 0.092(4) 0.078(4) -0.027(3) 0.027(3) -0.009(3) C13 0.050(3) 0.060(3) 0.066(3) 0.003(3) 0.013(2) -0.001(2) C14 0.048(3) 0.071(3) 0.049(3) 0.002(2) 0.008(2) 0.000(2) C15 0.068(3) 0.053(3) 0.067(3) -0.006(3) 0.006(3) 0.003(3) C16 0.086(4) 0.067(4) 0.075(4) -0.011(3) 0.019(3) -0.020(3) C17 0.087(4) 0.045(3) 0.046(3) -0.011(2) 0.007(3) -0.010(3) C18 0.122(5) 0.052(3) 0.063(3) -0.003(3) -0.003(3) 0.002(3) C19 0.096(4) 0.051(3) 0.070(3) -0.020(3) 0.006(3) -0.003(3) C20 0.082(4) 0.078(4) 0.044(3) -0.002(3) -0.006(3) 0.014(3) C21 0.084(4) 0.042(3) 0.073(3) -0.004(2) 0.016(3) 0.004(3) C22 0.098(4) 0.042(3) 0.091(4) 0.002(3) -0.010(3) 0.009(3) C23 0.083(4) 0.079(4) 0.050(3) -0.001(3) -0.006(3) 0.003(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 F1 1.386(6) . ? B F2 1.389(6) . ? B N2 1.543(6) . ? B N1 1.552(6) . ? N1 C1 1.355(5) . ? N1 C4 1.404(5) . ? N2 C9 1.349(5) . ? N2 C6 1.406(5) . ? O1 C17 1.425(6) . ? O1 C13 1.466(6) . ? O2 C16 1.416(6) . ? O2 C17 1.421(6) . ? C1 C2 1.402(6) . ? C1 C21 1.489(6) . ? C2 C3 1.375(7) . ? C3 C4 1.423(6) . ? C3 C20 1.512(6) . ? C4 C5 1.406(6) . ? C5 C6 1.402(6) . ? C5 C10 1.509(6) . ? C6 C7 1.426(6) . ? C7 C8 1.382(7) . ? C7 C22 1.489(7) . ? C8 C9 1.392(7) . ? C9 C23 1.507(7) . ? C10 C15 1.337(7) . ? C10 C11 1.419(7) . ? C11 C12 1.383(7) . ? C12 C13 1.343(7) . ? C13 C14 1.360(7) . ? C14 C16 1.453(7) . ? C14 C15 1.470(7) . ? C17 C19 1.495(7) . ? C17 C18 1.510(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 F1 B F2 109.5(4) . . ? F1 B N2 110.5(4) . . ? F2 B N2 109.6(4) . . ? F1 B N1 110.2(4) . . ? F2 B N1 109.8(4) . . ? N2 B N1 107.2(3) . . ? C1 N1 C4 107.8(3) . . ? C1 N1 B 126.5(4) . . ? C4 N1 B 125.7(3) . . ? C9 N2 C6 107.7(4) . . ? C9 N2 B 126.8(4) . . ? C6 N2 B 125.5(3) . . ? C17 O1 C13 113.7(4) . . ? C16 O2 C17 116.4(4) . . ? N1 C1 C2 109.3(4) . . ? N1 C1 C21 123.8(4) . . ? C2 C1 C21 126.9(4) . . ? C3 C2 C1 108.2(4) . . ? C2 C3 C4 107.0(4) . . ? C2 C3 C20 124.3(4) . . ? C4 C3 C20 128.6(4) . . ? N1 C4 C5 119.8(4) . . ? N1 C4 C3 107.6(4) . . ? C5 C4 C3 132.6(4) . . ? C6 C5 C4 121.5(4) . . ? C6 C5 C10 119.3(4) . . ? C4 C5 C10 119.1(4) . . ? C5 C6 N2 120.3(4) . . ? C5 C6 C7 131.8(4) . . ? N2 C6 C7 107.9(4) . . ? C8 C7 C6 106.1(4) . . ? C8 C7 C22 124.7(4) . . ? C6 C7 C22 129.3(4) . . ? C7 C8 C9 108.8(4) . . ? N2 C9 C8 109.6(4) . . ? N2 C9 C23 122.3(4) . . ? C8 C9 C23 128.1(4) . . ? C15 C10 C11 119.1(5) . . ? C15 C10 C5 121.7(5) . . ? C11 C10 C5 119.1(4) . . ? C12 C11 C10 120.9(5) . . ? C13 C12 C11 117.3(5) . . ? C12 C13 C14 126.9(5) . . ? C12 C13 O1 114.2(4) . . ? C14 C13 O1 118.8(4) . . ? C13 C14 C16 123.9(5) . . ? C13 C14 C15 114.2(4) . . ? C16 C14 C15 121.8(5) . . ? C10 C15 C14 121.5(5) . . ? O2 C16 C14 108.2(5) . . ? O2 C17 O1 109.0(4) . . ? O2 C17 C19 105.1(4) . . ? O1 C17 C19 106.4(4) . . ? O2 C17 C18 112.3(5) . . ? O1 C17 C18 109.3(4) . . ? C19 C17 C18 114.4(4) . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 23.10 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.766 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.061