# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _publ_contact_author_email lsy@uoregon.edu _publ_contact_author_name 'Shih-Yuan Liu' loop_ _publ_author_name 'Shih-Yuan Liu' 'Adam Marwitz' 'Lev Zakharov' 'David Dixon' 'Monica Vasiliu' # Attachment '- BN2_liu60.cif' data_liu60 _database_code_depnum_ccdc_archive 'CCDC 787729' #TrackingRef '- BN2_liu60.cif' _audit_creation_method SHELXLTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 B2 N2' _chemical_formula_weight 179.82 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 19.076(6) _cell_length_b 9.301(3) _cell_length_c 10.997(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1951.1(10) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1288 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 24.02 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9762 _exptl_absorpt_correction_T_max 0.9915 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 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 9364 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2125 _reflns_number_gt 1490 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0475P)^2^+0.3261P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2125 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0743 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1157 _refine_ls_wR_factor_gt 0.1012 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 N1 N 0.37741(8) 0.09010(15) 0.19502(12) 0.0348(4) Uani 1 1 d . . . N2 N 0.57515(8) -0.30599(15) 0.38015(13) 0.0360(4) Uani 1 1 d . . . B1 B 0.36983(10) 0.04068(19) 0.31694(16) 0.0308(4) Uani 1 1 d . . . B2 B 0.51903(10) -0.26120(19) 0.45777(17) 0.0314(4) Uani 1 1 d . . . C1 C 0.33583(10) 0.19310(19) 0.14516(16) 0.0400(4) Uani 1 1 d . . . C2 C 0.28294(10) 0.25244(19) 0.20983(17) 0.0410(5) Uani 1 1 d . . . C3 C 0.26966(9) 0.20815(19) 0.33054(17) 0.0409(4) Uani 1 1 d . . . C4 C 0.30961(9) 0.10596(18) 0.38546(16) 0.0367(4) Uani 1 1 d . . . C5 C 0.42214(9) -0.07060(17) 0.36693(14) 0.0339(4) Uani 1 1 d . . . C6 C 0.46454(9) -0.15497(17) 0.40696(14) 0.0343(4) Uani 1 1 d . . . C7 C 0.51957(9) -0.32486(18) 0.58305(15) 0.0345(4) Uani 1 1 d . . . C8 C 0.57066(10) -0.42005(18) 0.61355(16) 0.0391(4) Uani 1 1 d . . . C9 C 0.62351(9) -0.45874(19) 0.53015(18) 0.0412(5) Uani 1 1 d . . . C10 C 0.62532(9) -0.40181(18) 0.41637(17) 0.0395(4) Uani 1 1 d . . . H1N H 0.4117(10) 0.0596(19) 0.1497(17) 0.042(5) Uiso 1 1 d . . . H2N H 0.5797(10) -0.270(2) 0.2985(19) 0.056(6) Uiso 1 1 d . . . H1 H 0.3465(9) 0.2187(19) 0.0586(18) 0.053(5) Uiso 1 1 d . . . H2 H 0.2539(10) 0.329(2) 0.1738(17) 0.054(5) Uiso 1 1 d . . . H3 H 0.2307(10) 0.2560(19) 0.3723(17) 0.046(5) Uiso 1 1 d . . . H4 H 0.2994(10) 0.0819(18) 0.4694(17) 0.048(5) Uiso 1 1 d . . . H7 H 0.4856(10) -0.3024(19) 0.6422(18) 0.050(5) Uiso 1 1 d . . . H8 H 0.5720(10) -0.4656(19) 0.6964(17) 0.051(5) Uiso 1 1 d . . . H9 H 0.6606(9) -0.5242(19) 0.5534(15) 0.042(5) Uiso 1 1 d . . . H10 H 0.6624(9) -0.4290(18) 0.3529(17) 0.049(5) 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 N1 0.0377(8) 0.0387(8) 0.0280(8) 0.0002(6) 0.0043(6) 0.0032(7) N2 0.0413(8) 0.0369(8) 0.0296(8) 0.0003(6) 0.0020(6) -0.0013(7) B1 0.0339(10) 0.0306(9) 0.0278(10) -0.0004(7) -0.0001(8) -0.0051(8) B2 0.0355(10) 0.0287(9) 0.0300(10) -0.0020(7) -0.0015(8) -0.0021(8) C1 0.0451(11) 0.0456(10) 0.0293(9) 0.0073(8) -0.0036(8) 0.0009(9) C2 0.0379(10) 0.0403(10) 0.0448(11) 0.0076(8) -0.0057(8) 0.0026(8) C3 0.0340(10) 0.0417(10) 0.0471(11) 0.0011(8) 0.0070(8) 0.0038(8) C4 0.0396(10) 0.0386(9) 0.0320(9) 0.0031(7) 0.0058(8) -0.0019(8) C5 0.0400(10) 0.0361(9) 0.0256(8) -0.0009(7) 0.0035(7) -0.0012(8) C6 0.0430(10) 0.0354(9) 0.0244(8) -0.0017(6) 0.0024(7) 0.0000(8) C7 0.0386(10) 0.0364(9) 0.0285(9) -0.0007(7) 0.0012(8) 0.0013(8) C8 0.0457(11) 0.0376(9) 0.0340(10) 0.0031(8) -0.0079(8) -0.0014(8) C9 0.0354(10) 0.0357(10) 0.0526(12) -0.0025(8) -0.0119(9) 0.0051(8) C10 0.0342(9) 0.0382(10) 0.0463(11) -0.0068(8) 0.0018(8) 0.0002(8) _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 N1 C1 1.359(2) . ? N1 B1 1.425(2) . ? N2 C10 1.367(2) . ? N2 B2 1.431(2) . ? B1 C4 1.502(3) . ? B1 C5 1.539(3) . ? B2 C7 1.500(2) . ? B2 C6 1.539(2) . ? C1 C2 1.352(3) . ? C2 C3 1.413(3) . ? C3 C4 1.360(2) . ? C5 C6 1.210(2) . ? C7 C8 1.359(2) . ? C8 C9 1.410(3) . ? C9 C10 1.359(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 B1 123.22(16) . . ? C10 N2 B2 122.66(15) . . ? N1 B1 C4 114.79(15) . . ? N1 B1 C5 119.16(15) . . ? C4 B1 C5 126.04(15) . . ? N2 B2 C7 115.34(16) . . ? N2 B2 C6 118.39(15) . . ? C7 B2 C6 126.27(16) . . ? C2 C1 N1 120.72(17) . . ? C1 C2 C3 120.60(17) . . ? C4 C3 C2 121.37(17) . . ? C3 C4 B1 119.24(16) . . ? C6 C5 B1 178.17(18) . . ? C5 C6 B2 179.45(18) . . ? C8 C7 B2 119.27(17) . . ? C7 C8 C9 121.25(17) . . ? C10 C9 C8 121.18(17) . . ? C9 C10 N2 120.30(17) . . ? 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 C1 N1 B1 C4 2.9(2) . . . . ? C1 N1 B1 C5 -176.74(15) . . . . ? C10 N2 B2 C7 1.0(2) . . . . ? C10 N2 B2 C6 -178.84(15) . . . . ? B1 N1 C1 C2 -1.6(3) . . . . ? N1 C1 C2 C3 -0.2(3) . . . . ? C1 C2 C3 C4 0.5(3) . . . . ? C2 C3 C4 B1 1.0(3) . . . . ? N1 B1 C4 C3 -2.6(2) . . . . ? C5 B1 C4 C3 177.05(16) . . . . ? N1 B1 C5 C6 83(5) . . . . ? C4 B1 C5 C6 -96(5) . . . . ? B1 C5 C6 B2 -18(22) . . . . ? N2 B2 C6 C5 -64(19) . . . . ? C7 B2 C6 C5 116(19) . . . . ? N2 B2 C7 C8 -1.3(2) . . . . ? C6 B2 C7 C8 178.56(15) . . . . ? B2 C7 C8 C9 0.7(3) . . . . ? C7 C8 C9 C10 0.2(3) . . . . ? C8 C9 C10 N2 -0.5(3) . . . . ? B2 N2 C10 C9 -0.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.170 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.036 data_liu72 _database_code_depnum_ccdc_archive 'CCDC 787730' #TrackingRef '- BN1_liu72.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 B N' _chemical_formula_weight 179.02 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 23.388(11) _cell_length_b 31.934(15) _cell_length_c 5.423(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4051(3) _cell_formula_units_Z 16 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 748 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 17.66 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.174 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9860 _exptl_absorpt_correction_T_max 0.9987 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 8757 _diffrn_reflns_av_R_equivalents 0.0942 _diffrn_reflns_av_sigmaI/netI 0.0762 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1791 _reflns_number_gt 1224 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0482P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmep _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(6) _refine_ls_number_reflns 1791 _refine_ls_number_parameters 167 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0946 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.1198 _refine_ls_wR_factor_gt 0.1043 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 N1 N 0.06008(13) 0.10008(9) 0.4888(6) 0.0409(8) Uani 1 1 d . . . B1 B 0.01218(16) 0.09166(11) 0.3334(8) 0.0327(9) Uani 1 1 d . . . C1 C 0.10125(16) 0.12964(11) 0.4348(8) 0.0424(10) Uani 1 1 d . . . C2 C 0.09739(15) 0.15251(11) 0.2256(7) 0.0401(10) Uani 1 1 d . . . C3 C 0.05139(16) 0.14621(11) 0.0595(8) 0.0417(10) Uani 1 1 d . . . C4 C 0.00955(16) 0.11727(10) 0.1045(7) 0.0406(10) Uani 1 1 d . . . C5 C -0.03190(14) 0.05959(10) 0.4301(7) 0.0372(9) Uani 1 1 d . . . C6 C -0.06654(14) 0.03522(11) 0.5158(7) 0.0363(8) Uani 1 1 d . . . C7 C -0.10768(14) 0.00652(9) 0.6161(6) 0.0329(9) Uani 1 1 d . . . C8 C -0.09648(17) -0.01535(10) 0.8367(7) 0.0401(9) Uani 1 1 d . . . C9 C -0.1367(2) -0.04377(11) 0.9266(8) 0.0489(11) Uani 1 1 d . . . C10 C -0.1877(2) -0.05019(13) 0.8034(9) 0.0550(12) Uani 1 1 d . . . C11 C -0.19986(17) -0.02798(12) 0.5913(9) 0.0485(11) Uani 1 1 d . . . C12 C -0.16013(15) 0.00001(11) 0.4952(7) 0.0410(10) Uani 1 1 d . . . H1N H 0.0625(18) 0.0847(13) 0.632(9) 0.095(17) Uiso 1 1 d . . . H1 H 0.1305(18) 0.1315(12) 0.580(8) 0.086(14) Uiso 1 1 d . . . H2 H 0.1276(13) 0.1720(9) 0.202(6) 0.038(9) Uiso 1 1 d . . . H3 H 0.0510(12) 0.1603(9) -0.087(6) 0.027(9) Uiso 1 1 d . . . H4 H -0.0198(13) 0.1130(9) -0.008(7) 0.037(10) Uiso 1 1 d . . . H8 H -0.0627(19) -0.0114(13) 0.931(9) 0.086(16) Uiso 1 1 d . . . H9 H -0.1282(15) -0.0564(11) 1.083(8) 0.053(11) Uiso 1 1 d . . . H10 H -0.2172(17) -0.0674(12) 0.876(8) 0.074(14) Uiso 1 1 d . . . H11 H -0.2353(14) -0.0314(10) 0.493(8) 0.051(11) Uiso 1 1 d . . . H12 H -0.1658(13) 0.0156(9) 0.351(7) 0.039(10) 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 N1 0.0492(19) 0.0302(18) 0.043(2) 0.0078(15) -0.0059(16) -0.0074(15) B1 0.032(2) 0.0189(18) 0.047(2) -0.0020(19) -0.001(2) 0.0036(16) C1 0.047(3) 0.034(2) 0.046(3) 0.0038(19) -0.0023(19) -0.0134(17) C2 0.042(2) 0.026(2) 0.052(2) 0.0020(17) 0.006(2) -0.0053(17) C3 0.046(2) 0.035(2) 0.045(3) 0.011(2) 0.003(2) 0.0035(18) C4 0.037(2) 0.036(2) 0.048(3) 0.0011(19) -0.0026(19) 0.0004(17) C5 0.036(2) 0.0266(18) 0.048(2) -0.0002(16) -0.0009(18) 0.0058(16) C6 0.041(2) 0.0252(18) 0.043(2) -0.0025(16) -0.0016(17) 0.0062(17) C7 0.039(2) 0.0186(15) 0.041(2) -0.0057(15) 0.0040(17) 0.0013(14) C8 0.055(3) 0.0208(17) 0.044(2) -0.0064(16) 0.005(2) 0.0074(17) C9 0.077(3) 0.028(2) 0.042(3) 0.0039(18) 0.019(2) 0.003(2) C10 0.057(3) 0.035(2) 0.073(3) -0.006(2) 0.027(3) -0.007(2) C11 0.043(2) 0.036(2) 0.066(3) -0.007(2) 0.008(2) -0.0111(18) C12 0.046(2) 0.028(2) 0.049(3) -0.0048(18) 0.007(2) -0.0027(18) _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 N1 C1 1.380(4) . ? N1 B1 1.427(5) . ? N1 H1N 0.92(5) . ? B1 C4 1.488(5) . ? B1 C5 1.545(5) . ? C1 C2 1.352(5) . ? C1 H1 1.04(4) . ? C2 C3 1.417(5) . ? C2 H2 0.95(3) . ? C3 C4 1.368(5) . ? C3 H3 0.91(3) . ? C4 H4 0.93(3) . ? C5 C6 1.216(4) . ? C6 C7 1.436(5) . ? C7 C12 1.406(5) . ? C7 C8 1.410(5) . ? C8 C9 1.395(5) . ? C8 H8 0.95(5) . ? C9 C10 1.383(6) . ? C9 H9 0.96(4) . ? C10 C11 1.381(6) . ? C10 H10 0.96(4) . ? C11 C12 1.391(5) . ? C11 H11 0.99(4) . ? C12 H12 0.94(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 B1 123.5(3) . . ? C1 N1 H1N 120(3) . . ? B1 N1 H1N 116(3) . . ? N1 B1 C4 114.9(3) . . ? N1 B1 C5 116.6(3) . . ? C4 B1 C5 128.3(3) . . ? C2 C1 N1 120.0(4) . . ? C2 C1 H1 130(2) . . ? N1 C1 H1 110(2) . . ? C1 C2 C3 120.5(3) . . ? C1 C2 H2 115(2) . . ? C3 C2 H2 125(2) . . ? C4 C3 C2 121.7(4) . . ? C4 C3 H3 118.8(19) . . ? C2 C3 H3 119.4(19) . . ? C3 C4 B1 119.4(4) . . ? C3 C4 H4 121(2) . . ? B1 C4 H4 120(2) . . ? C6 C5 B1 177.2(4) . . ? C5 C6 C7 179.7(4) . . ? C12 C7 C8 119.0(3) . . ? C12 C7 C6 120.1(3) . . ? C8 C7 C6 120.9(3) . . ? C9 C8 C7 119.6(4) . . ? C9 C8 H8 117(3) . . ? C7 C8 H8 123(3) . . ? C10 C9 C8 120.6(4) . . ? C10 C9 H9 123(2) . . ? C8 C9 H9 116(2) . . ? C11 C10 C9 120.2(4) . . ? C11 C10 H10 119(3) . . ? C9 C10 H10 120(3) . . ? C10 C11 C12 120.3(4) . . ? C10 C11 H11 124(2) . . ? C12 C11 H11 115(2) . . ? C11 C12 C7 120.2(4) . . ? C11 C12 H12 124(2) . . ? C7 C12 H12 116(2) . . ? 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 C1 N1 B1 C4 0.2(5) . . . . ? C1 N1 B1 C5 -176.1(3) . . . . ? B1 N1 C1 C2 0.1(5) . . . . ? N1 C1 C2 C3 -0.4(5) . . . . ? C1 C2 C3 C4 0.3(6) . . . . ? C2 C3 C4 B1 0.0(5) . . . . ? N1 B1 C4 C3 -0.2(5) . . . . ? C5 B1 C4 C3 175.6(4) . . . . ? N1 B1 C5 C6 47(7) . . . . ? C4 B1 C5 C6 -129(7) . . . . ? B1 C5 C6 C7 120(100) . . . . ? C5 C6 C7 C12 6(92) . . . . ? C5 C6 C7 C8 -173(100) . . . . ? C12 C7 C8 C9 1.9(4) . . . . ? C6 C7 C8 C9 -178.5(3) . . . . ? C7 C8 C9 C10 -1.0(5) . . . . ? C8 C9 C10 C11 -1.0(6) . . . . ? C9 C10 C11 C12 2.1(6) . . . . ? C10 C11 C12 C7 -1.2(5) . . . . ? C8 C7 C12 C11 -0.8(5) . . . . ? C6 C7 C12 C11 179.6(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.143 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.037