# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_contact_author 'Nicholas C. Norman' _publ_contact_author_email n.c.norman@bristol.ac.uk _publ_section_title ; 1,1- and 1,2-Isomers of the Diborane(4) Compound B2{1,2-(NH)2C6H4}2 and a TCNQ Co-crystal of the 1,1-Isomer ; _publ_contact_author_name 'Nicholas C. Norman' loop_ _publ_author_name 'Muhsen A. M. Alibadi' 'Andrei S. Batsanov' 'George Bramham' 'Jonathan P. H. Charmant' ; M.F.Haddow ; 'Laura MacKay' 'John E. McGrady' 'Nicholas C. Norman' 'Anna Roffey' 'Christopher A. Russell' data_2a _database_code_depnum_ccdc_archive 'CCDC 713336' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 1,1-Bis(o-phenyldiamino-N,N')diboron _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 B2 N4' _chemical_formula_sum 'C12 H12 B2 N4' _chemical_formula_weight 233.88 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 Monoclinic _symmetry_space_group_name_H-M 'P 2(1)/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 5.7877(12) _cell_length_b 7.4285(15) _cell_length_c 13.219(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00(3) _cell_angle_gamma 90.00 _cell_volume 568.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1167 _cell_measurement_theta_min 3.075 _cell_measurement_theta_max 25.142 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.910 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details 'SADABS U2.10(BRUKER-AXS,2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'omega scans' _diffrn_detector_area_resol_mean 8.5 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6493 _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1306 _reflns_number_gt 1199 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0362P)^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 0 _refine_ls_number_reflns 1306 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0553 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1001 _refine_ls_wR_factor_gt 0.0986 _refine_ls_goodness_of_fit_ref 1.479 _refine_ls_restrained_S_all 1.479 _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 0.5565(4) 0.4875(3) 0.05803(17) 0.0191(5) Uani 1 1 d . . . N1 N 0.7718(3) 0.40343(18) 0.08540(12) 0.0193(4) Uani 1 1 d . . . H1 H 0.8686 0.3568 0.0436 0.023 Uiso 1 1 calc R . . N2 N 0.4606(3) 0.54408(18) 0.15319(12) 0.0177(4) Uani 1 1 d . . . H2 H 0.3311 0.5996 0.1602 0.021 Uiso 1 1 calc R . . C1 C 0.7991(4) 0.4092(2) 0.18982(14) 0.0171(4) Uani 1 1 d . . . C2 C 0.6058(3) 0.4966(2) 0.23173(15) 0.0172(4) Uani 1 1 d . . . C3 C 0.5871(4) 0.5245(2) 0.33503(15) 0.0197(4) Uani 1 1 d . . . H3 H 0.4592 0.5825 0.3625 0.024 Uiso 1 1 calc R . . C4 C 0.7653(4) 0.4630(2) 0.39616(14) 0.0212(5) Uani 1 1 d . . . H4 H 0.7574 0.4807 0.4657 0.025 Uiso 1 1 calc R . . C5 C 0.9571(4) 0.3747(2) 0.35450(16) 0.0223(5) Uani 1 1 d . . . H5 H 1.0737 0.3339 0.3972 0.027 Uiso 1 1 calc R . . C6 C 0.9770(3) 0.3468(2) 0.25109(14) 0.0197(4) Uani 1 1 d . . . H6 H 1.1048 0.2885 0.2238 0.024 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 0.0250(12) 0.0105(9) 0.0217(12) -0.0001(8) 0.0005(12) -0.0042(8) N1 0.0249(10) 0.0143(7) 0.0187(8) -0.0022(6) 0.0027(8) 0.0000(7) N2 0.0197(8) 0.0155(7) 0.0179(9) 0.0008(6) 0.0004(8) 0.0019(6) C1 0.0235(11) 0.0103(8) 0.0174(9) -0.0002(7) 0.0052(8) -0.0034(7) C2 0.0207(10) 0.0081(8) 0.0228(10) 0.0009(7) 0.0005(9) -0.0026(7) C3 0.0249(11) 0.0147(8) 0.0196(10) -0.0003(7) 0.0071(10) 0.0003(7) C4 0.0325(12) 0.0161(8) 0.0150(9) -0.0004(6) -0.0007(10) -0.0052(9) C5 0.0241(11) 0.0148(8) 0.0279(11) 0.0036(8) -0.0063(11) -0.0038(7) C6 0.0182(10) 0.0145(9) 0.0265(11) 0.0004(7) 0.0022(9) -0.0007(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 B1 N2 1.438(3) . ? B1 N1 1.440(3) . ? B1 B1 1.678(5) 3_665 ? N1 C1 1.390(2) . ? N1 H1 0.8600 . ? N2 C2 1.382(2) . ? N2 H2 0.8600 . ? C1 C6 1.389(3) . ? C1 C2 1.407(3) . ? C2 C3 1.385(3) . ? C3 C4 1.388(3) . ? C3 H3 0.9300 . ? C4 C5 1.402(3) . ? C4 H4 0.9300 . ? C5 C6 1.387(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? 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 N2 B1 N1 103.95(18) . . ? N2 B1 B1 128.1(2) . 3_665 ? N1 B1 B1 127.9(2) . 3_665 ? C1 N1 B1 109.56(17) . . ? C1 N1 H1 125.2 . . ? B1 N1 H1 125.2 . . ? C2 N2 B1 110.36(17) . . ? C2 N2 H2 124.9 . . ? B1 N2 H2 124.9 . . ? C6 C1 N1 130.78(19) . . ? C6 C1 C2 120.89(17) . . ? N1 C1 C2 108.32(18) . . ? N2 C2 C3 130.90(19) . . ? N2 C2 C1 107.81(16) . . ? C3 C2 C1 121.29(19) . . ? C4 C3 C2 117.81(19) . . ? C4 C3 H3 121.1 . . ? C2 C3 H3 121.1 . . ? C3 C4 C5 120.92(18) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C6 C5 C4 121.50(19) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C1 C6 C5 117.59(19) . . ? C1 C6 H6 121.2 . . ? C5 C6 H6 121.2 . . ? 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 N2 B1 N1 C1 0.44(18) . . . . ? B1 B1 N1 C1 -179.3(2) 3_665 . . . ? N1 B1 N2 C2 -0.41(18) . . . . ? B1 B1 N2 C2 179.3(2) 3_665 . . . ? B1 N1 C1 C6 -179.70(18) . . . . ? B1 N1 C1 C2 -0.32(19) . . . . ? B1 N2 C2 C3 179.18(18) . . . . ? B1 N2 C2 C1 0.24(19) . . . . ? C6 C1 C2 N2 179.50(16) . . . . ? N1 C1 C2 N2 0.05(19) . . . . ? C6 C1 C2 C3 0.4(3) . . . . ? N1 C1 C2 C3 -179.01(16) . . . . ? N2 C2 C3 C4 -178.92(17) . . . . ? C1 C2 C3 C4 -0.1(3) . . . . ? C2 C3 C4 C5 -0.4(3) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? N1 C1 C6 C5 179.04(18) . . . . ? C2 C1 C6 C5 -0.3(3) . . . . ? C4 C5 C6 C1 -0.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.262 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.055 data_2b _database_code_depnum_ccdc_archive 'CCDC 713337' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 1,2-Bis(o-phenyldiamino-N,N')diboron _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 B2 N4' _chemical_formula_sum 'C12 H12 B2 N4' _chemical_formula_weight 233.88 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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.7750(12) _cell_length_b 7.8242(16) _cell_length_c 12.487(3) _cell_angle_alpha 100.45(3) _cell_angle_beta 101.05(3) _cell_angle_gamma 94.63(3) _cell_volume 540.66(19) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1541 _cell_measurement_theta_min 2.6665 _cell_measurement_theta_max 27.396 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 0.96 _exptl_absorpt_process_details 'SADABS U2.10(BRUKER-AXS,2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'omega scans' _diffrn_detector_area_resol_mean 8.5 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6229 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0483 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2468 _reflns_number_gt 1776 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0858P)^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 0 _refine_ls_number_reflns 2468 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0675 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1530 _refine_ls_wR_factor_gt 0.1316 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _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 -0.1314(3) 0.9448(2) 0.99367(14) 0.0129(4) Uani 1 1 d . . . N1 N -0.2168(2) 0.81997(15) 0.89326(10) 0.0136(3) Uani 1 1 d . . . H1 H -0.3528 0.7543 0.8846 0.016 Uiso 1 1 calc R . . N2 N 0.2442(2) 1.01765(15) 0.91491(10) 0.0132(3) Uani 1 1 d . . . H6 H 0.3859 1.0724 0.9191 0.016 Uiso 1 1 calc R . . C1 C -0.0893(3) 0.79824(18) 0.80679(12) 0.0130(3) Uani 1 1 d . . . C2 C -0.1865(3) 0.67938(18) 0.70778(12) 0.0147(3) Uani 1 1 d . . . H2 H -0.3362 0.6134 0.7004 0.018 Uiso 1 1 calc R . . C3 C -0.0706(3) 0.65471(19) 0.61964(12) 0.0165(4) Uani 1 1 d . . . H3 H -0.1403 0.5727 0.5530 0.020 Uiso 1 1 calc R . . C4 C 0.1479(3) 0.75054(19) 0.62944(12) 0.0170(4) Uani 1 1 d . . . H4 H 0.2282 0.7353 0.5693 0.020 Uiso 1 1 calc R . . C5 C 0.2483(3) 0.86881(18) 0.72760(12) 0.0148(3) Uani 1 1 d . . . H5 H 0.3982 0.9338 0.7338 0.018 Uiso 1 1 calc R . . C6 C 0.1353(2) 0.89493(18) 0.81742(12) 0.0130(3) Uani 1 1 d . . . B2 B 0.3729(3) 0.5305(2) -0.02844(14) 0.0139(4) Uani 1 1 d . . . N3 N 0.2563(2) 0.63332(15) 0.04571(10) 0.0142(3) Uani 1 1 d . . . H8 H 0.1205 0.6690 0.0189 0.017 Uiso 1 1 calc R . . N4 N 0.2973(2) 0.47612(15) -0.14526(10) 0.0146(3) Uani 1 1 d . . . H7 H 0.1650 0.5092 -0.1788 0.018 Uiso 1 1 calc R . . C7 C 0.3520(3) 0.68016(18) 0.16133(12) 0.0139(3) Uani 1 1 d . . . C8 C 0.2270(3) 0.77865(18) 0.23072(12) 0.0153(3) Uani 1 1 d . . . H9 H 0.0789 0.8123 0.1989 0.018 Uiso 1 1 calc R . . C9 C 0.3134(3) 0.82855(19) 0.34459(12) 0.0167(4) Uani 1 1 d . . . H10 H 0.2243 0.8946 0.3901 0.020 Uiso 1 1 calc R . . C10 C 0.5304(3) 0.78173(19) 0.39197(12) 0.0172(4) Uani 1 1 d . . . H11 H 0.5916 0.8161 0.4699 0.021 Uiso 1 1 calc R . . C11 C 0.6573(3) 0.68398(18) 0.32425(12) 0.0155(3) Uani 1 1 d . . . H12 H 0.8067 0.6533 0.3570 0.019 Uiso 1 1 calc R . . C12 C 0.5722(3) 0.62959(18) 0.20969(12) 0.0138(3) Uani 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 B1 0.0128(8) 0.0129(8) 0.0147(8) 0.0062(7) 0.0031(7) 0.0034(6) N1 0.0107(6) 0.0148(6) 0.0159(7) 0.0034(5) 0.0051(5) -0.0019(5) N2 0.0095(6) 0.0150(6) 0.0146(7) 0.0036(5) 0.0017(5) -0.0016(5) C1 0.0135(7) 0.0129(7) 0.0146(8) 0.0057(6) 0.0046(6) 0.0032(6) C2 0.0141(7) 0.0138(7) 0.0162(8) 0.0049(6) 0.0016(6) 0.0010(6) C3 0.0200(8) 0.0148(7) 0.0140(8) 0.0018(6) 0.0021(6) 0.0032(6) C4 0.0193(8) 0.0186(8) 0.0155(8) 0.0053(6) 0.0073(6) 0.0042(6) C5 0.0134(7) 0.0155(7) 0.0175(8) 0.0063(6) 0.0055(6) 0.0025(6) C6 0.0129(7) 0.0128(7) 0.0144(7) 0.0049(6) 0.0027(6) 0.0021(6) B2 0.0125(8) 0.0112(8) 0.0185(9) 0.0048(7) 0.0038(7) -0.0008(6) N3 0.0114(6) 0.0164(6) 0.0150(7) 0.0046(5) 0.0006(5) 0.0034(5) N4 0.0114(6) 0.0157(6) 0.0173(7) 0.0046(5) 0.0017(5) 0.0046(5) C7 0.0139(7) 0.0114(7) 0.0162(8) 0.0040(6) 0.0026(6) -0.0008(6) C8 0.0124(7) 0.0131(7) 0.0213(8) 0.0058(6) 0.0042(6) 0.0002(6) C9 0.0177(8) 0.0148(7) 0.0191(8) 0.0026(6) 0.0086(6) 0.0005(6) C10 0.0191(8) 0.0166(8) 0.0156(8) 0.0037(6) 0.0037(6) -0.0012(6) C11 0.0143(7) 0.0151(7) 0.0176(8) 0.0064(6) 0.0022(6) -0.0001(6) C12 0.0128(7) 0.0117(7) 0.0179(8) 0.0051(6) 0.0044(6) 0.0001(6) _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 N2 1.417(2) 2_577 ? B1 N1 1.418(2) . ? B1 B1 1.649(3) 2_577 ? N1 C1 1.4126(18) . ? N1 H1 0.8800 . ? N2 C6 1.4087(19) . ? N2 B1 1.417(2) 2_577 ? N2 H6 0.8800 . ? C1 C2 1.393(2) . ? C1 C6 1.419(2) . ? C2 C3 1.387(2) . ? C2 H2 0.9500 . ? C3 C4 1.387(2) . ? C3 H3 0.9500 . ? C4 C5 1.387(2) . ? C4 H4 0.9500 . ? C5 C6 1.394(2) . ? C5 H5 0.9500 . ? B2 N4 1.414(2) . ? B2 N3 1.419(2) . ? B2 B2 1.651(3) 2_665 ? N3 C7 1.4119(19) . ? N3 H8 0.8800 . ? N4 C12 1.4110(19) 2_665 ? N4 H7 0.8800 . ? C7 C8 1.398(2) . ? C7 C12 1.418(2) . ? C8 C9 1.385(2) . ? C8 H9 0.9500 . ? C9 C10 1.387(2) . ? C9 H10 0.9500 . ? C10 C11 1.390(2) . ? C10 H11 0.9500 . ? C11 C12 1.395(2) . ? C11 H12 0.9500 . ? C12 N4 1.4110(19) 2_665 ? 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 N2 B1 N1 127.24(14) 2_577 . ? N2 B1 B1 116.56(17) 2_577 2_577 ? N1 B1 B1 116.18(17) . 2_577 ? C1 N1 B1 121.71(13) . . ? C1 N1 H1 119.1 . . ? B1 N1 H1 119.1 . . ? C6 N2 B1 121.68(12) . 2_577 ? C6 N2 H6 119.2 . . ? B1 N2 H6 119.2 2_577 . ? C2 C1 N1 119.38(13) . . ? C2 C1 C6 118.74(14) . . ? N1 C1 C6 121.88(14) . . ? C3 C2 C1 121.77(14) . . ? C3 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? C2 C3 C4 119.56(14) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 119.55(14) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C4 C5 C6 121.81(14) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C5 C6 N2 119.53(13) . . ? C5 C6 C1 118.57(14) . . ? N2 C6 C1 121.90(13) . . ? N4 B2 N3 127.46(14) . . ? N4 B2 B2 116.50(17) . 2_665 ? N3 B2 B2 116.04(17) . 2_665 ? C7 N3 B2 121.94(13) . . ? C7 N3 H8 119.0 . . ? B2 N3 H8 119.0 . . ? C12 N4 B2 121.95(13) 2_665 . ? C12 N4 H7 119.0 2_665 . ? B2 N4 H7 119.0 . . ? C8 C7 N3 119.44(13) . . ? C8 C7 C12 118.69(14) . . ? N3 C7 C12 121.87(14) . . ? C9 C8 C7 121.74(14) . . ? C9 C8 H9 119.1 . . ? C7 C8 H9 119.1 . . ? C8 C9 C10 119.75(14) . . ? C8 C9 H10 120.1 . . ? C10 C9 H10 120.1 . . ? C9 C10 C11 119.32(14) . . ? C9 C10 H11 120.3 . . ? C11 C10 H11 120.3 . . ? C10 C11 C12 121.99(14) . . ? C10 C11 H12 119.0 . . ? C12 C11 H12 119.0 . . ? C11 C12 N4 119.84(13) . 2_665 ? C11 C12 C7 118.49(14) . . ? N4 C12 C7 121.65(14) 2_665 . ? 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 N2 B1 N1 C1 178.32(12) 2_577 . . . ? B1 B1 N1 C1 -3.2(2) 2_577 . . . ? B1 N1 C1 C2 -177.04(12) . . . . ? B1 N1 C1 C6 2.6(2) . . . . ? N1 C1 C2 C3 179.07(11) . . . . ? C6 C1 C2 C3 -0.6(2) . . . . ? C1 C2 C3 C4 -0.1(2) . . . . ? C2 C3 C4 C5 0.5(2) . . . . ? C3 C4 C5 C6 -0.2(2) . . . . ? C4 C5 C6 N2 -179.51(11) . . . . ? C4 C5 C6 C1 -0.5(2) . . . . ? B1 N2 C6 C5 176.87(12) 2_577 . . . ? B1 N2 C6 C1 -2.1(2) 2_577 . . . ? C2 C1 C6 C5 0.9(2) . . . . ? N1 C1 C6 C5 -178.75(11) . . . . ? C2 C1 C6 N2 179.84(12) . . . . ? N1 C1 C6 N2 0.2(2) . . . . ? N4 B2 N3 C7 -179.45(13) . . . . ? B2 B2 N3 C7 -0.2(2) 2_665 . . . ? N3 B2 N4 C12 -178.69(12) . . . 2_665 ? B2 B2 N4 C12 2.1(2) 2_665 . . 2_665 ? B2 N3 C7 C8 -178.68(12) . . . . ? B2 N3 C7 C12 1.1(2) . . . . ? N3 C7 C8 C9 -179.76(12) . . . . ? C12 C7 C8 C9 0.5(2) . . . . ? C7 C8 C9 C10 0.6(2) . . . . ? C8 C9 C10 C11 -0.5(2) . . . . ? C9 C10 C11 C12 -0.7(2) . . . . ? C10 C11 C12 N4 -177.15(11) . . . 2_665 ? C10 C11 C12 C7 1.7(2) . . . . ? C8 C7 C12 C11 -1.5(2) . . . . ? N3 C7 C12 C11 178.69(12) . . . . ? C8 C7 C12 N4 177.25(11) . . . 2_665 ? N3 C7 C12 N4 -2.5(2) . . . 2_665 ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.360 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.113 data_4 _database_code_depnum_ccdc_archive 'CCDC 713338' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 B2 N2 O2' _chemical_formula_sum 'C12 H10 B2 N2 O2' _chemical_formula_weight 235.84 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 9.2318(12) _cell_length_b 6.3856(8) _cell_length_c 10.2704(13) _cell_angle_alpha 90.00 _cell_angle_beta 113.29(2) _cell_angle_gamma 90.00 _cell_volume 556.11(12) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6636 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 30.02 _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 1.48 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.52 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.838 _exptl_absorpt_correction_T_max 0.952 _exptl_absorpt_process_details 'SADABS-2006/1 (Bruker), R(int)=0.098 before correction' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 1.00 -1.00 0.2700 0.00 -1.00 1.00 0.2700 0.00 1.00 1.00 0.3000 0.00 -1.00 -1.00 0.3000 -1.00 0.00 1.00 0.2600 1.00 0.00 -1.00 0.2600 _exptl_special_details ; The data collection nominally covered full sphere of reciprocal space, by a combination of 4 runs of narrow-frame \w-scans (scan width 0.3\% \w, 5s exposure), every run at a different \f angle. Crystal to detector distance 4.41 cm. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number 0 _diffrn_reflns_number 7430 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_sigmaI/netI 0.0110 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 30.02 _reflns_number_total 1583 _reflns_number_gt 1531 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.049 (Bruker, 1998)' _computing_cell_refinement 'SAINT version 6.45A (Bruker, 2003)' _computing_data_reduction 'SAINT version 6.45A (Bruker, 2003)' _computing_structure_solution 'SHELXTL version 6.14 (Bruker, 2003)' _computing_structure_refinement 'SHELXTL version 6.14 (Bruker, 2003)' _computing_molecular_graphics 'SHELXTL version 6.14 (Bruker, 2003)' _computing_publication_material 'SHELXTL version 6.14 (Bruker, 2003)' _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. ; _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^)+(0.0664P)^2^+0.1409P] 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 1583 _refine_ls_number_parameters 102 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1084 _refine_ls_wR_factor_gt 0.1075 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 O O 0.32040(7) 0.20178(10) 0.44882(6) 0.01770(17) Uani 1 1 d . . . N N 0.54931(8) 0.23889(12) 0.64586(8) 0.01756(18) Uani 1 1 d . . . H1 H 0.6484(18) 0.230(2) 0.7174(17) 0.037(4) Uiso 1 1 d . . . B B 0.46988(11) 0.11103(15) 0.52537(10) 0.0169(2) Uani 1 1 d . . . C1 C 0.31074(10) 0.37887(13) 0.52233(8) 0.01589(19) Uani 1 1 d . . . C2 C 0.44965(10) 0.40497(13) 0.64305(9) 0.01636(19) Uani 1 1 d . . . C3 C 0.46658(11) 0.57294(15) 0.73386(10) 0.0210(2) Uani 1 1 d . . . H3 H 0.5663(17) 0.594(2) 0.8189(15) 0.031(3) Uiso 1 1 d . . . C4 C 0.34001(12) 0.71163(14) 0.70017(10) 0.0224(2) Uani 1 1 d . . . H4 H 0.3490(17) 0.832(2) 0.7626(16) 0.034(4) Uiso 1 1 d . . . C5 C 0.20197(11) 0.68396(14) 0.57914(10) 0.0214(2) Uani 1 1 d . . . H5 H 0.1187(18) 0.786(3) 0.5599(17) 0.038(4) Uiso 1 1 d . . . C6 C 0.18523(10) 0.51565(14) 0.48703(9) 0.0198(2) Uani 1 1 d . . . H6 H 0.0875(17) 0.491(2) 0.4021(15) 0.031(4) 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 O 0.0164(3) 0.0173(3) 0.0165(3) -0.0023(2) 0.0034(2) 0.0015(2) N 0.0151(3) 0.0179(3) 0.0167(3) 0.0002(3) 0.0031(3) 0.0014(3) B 0.0160(4) 0.0168(4) 0.0163(4) 0.0011(3) 0.0047(3) 0.0005(3) C1 0.0163(4) 0.0157(4) 0.0152(4) -0.0003(3) 0.0057(3) 0.0000(3) C2 0.0158(4) 0.0166(4) 0.0159(4) 0.0008(3) 0.0054(3) -0.0004(3) C3 0.0208(4) 0.0212(4) 0.0195(4) -0.0039(3) 0.0065(3) -0.0029(3) C4 0.0262(4) 0.0190(4) 0.0243(4) -0.0043(3) 0.0126(4) -0.0015(3) C5 0.0231(4) 0.0194(4) 0.0240(4) 0.0012(3) 0.0117(3) 0.0040(3) C6 0.0178(4) 0.0218(4) 0.0188(4) 0.0014(3) 0.0060(3) 0.0031(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 O C1 1.3820(10) . ? O B 1.4143(11) . ? N C2 1.3968(11) . ? N B 1.4206(12) . ? N H1 0.921(16) . ? B B 1.6794(19) 3_656 ? C1 C6 1.3801(12) . ? C1 C2 1.3972(12) . ? C2 C3 1.3891(12) . ? C3 C4 1.3963(13) . ? C3 H3 0.996(15) . ? C4 C5 1.3955(14) . ? C4 H4 0.982(15) . ? C5 C6 1.3994(13) . ? C5 H5 0.968(16) . ? C6 H6 0.989(15) . ? 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 O B 106.93(7) . . ? C2 N B 108.03(7) . . ? C2 N H1 120.1(10) . . ? B N H1 131.8(10) . . ? O B N 107.63(8) . . ? O B B 122.92(9) . 3_656 ? N B B 129.44(10) . 3_656 ? C6 C1 O 127.10(8) . . ? C6 C1 C2 122.57(8) . . ? O C1 C2 110.33(7) . . ? C3 C2 N 132.38(8) . . ? C3 C2 C1 120.53(8) . . ? N C2 C1 107.08(7) . . ? C2 C3 C4 117.54(8) . . ? C2 C3 H3 120.9(8) . . ? C4 C3 H3 121.5(8) . . ? C5 C4 C3 121.36(8) . . ? C5 C4 H4 119.5(9) . . ? C3 C4 H4 119.2(9) . . ? C4 C5 C6 121.15(8) . . ? C4 C5 H5 117.9(9) . . ? C6 C5 H5 120.9(9) . . ? C1 C6 C5 116.85(8) . . ? C1 C6 H6 120.5(8) . . ? C5 C6 H6 122.6(8) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N H1 O 0.921(16) 2.319(16) 3.1513(13) 150.2(13) 4_666 _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.407 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.051 data_5 _database_code_depnum_ccdc_archive 'CCDC 713339' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 B2 N4,2(C12 H4 N4)' _chemical_formula_sum 'C36 H20 B2 N12' _chemical_formula_weight 642.26 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8802(9) _cell_length_b 8.4736(10) _cell_length_c 12.0672(14) _cell_angle_alpha 104.51(2) _cell_angle_beta 93.41(2) _cell_angle_gamma 91.51(2) _cell_volume 777.98(16) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5449 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 29.95 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 330 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.856 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details 'SADABS-2006/1 (Bruker)' _exptl_special_details ; The data collection nominally covered full sphere of reciprocal space, by a combination of 4 runs of narrow-frame \w-scans (scan width 0.3\% \w, 10s exposure), every run at a different \f angle. Crystal to detector distance 4.41 cm. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number 0 _diffrn_reflns_number 10805 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 29.00 _reflns_number_total 4103 _reflns_number_gt 3208 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.049 (Bruker, 1998)' _computing_cell_refinement 'SAINT version 6.45A (Bruker, 2003)' _computing_data_reduction 'SAINT version 6.45A (Bruker, 2003)' _computing_structure_solution 'SHELXTL version 6.14 (Bruker, 2003)' _computing_structure_refinement 'SHELXTL version 6.14 (Bruker, 2003)' _computing_molecular_graphics 'SHELXTL version 6.14 (Bruker, 2003)' _computing_publication_material 'SHELXTL version 6.14 (Bruker, 2003)' _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. ; _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^)+(0.0754P)^2^+0.1472P] 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 4103 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0624 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1332 _refine_ls_wR_factor_gt 0.1232 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 0.85436(14) 0.36913(14) 0.08619(9) 0.0203(2) Uani 1 1 d . . . H1 H 0.842(2) 0.263(3) 0.0451(18) 0.049(6) Uiso 1 1 d . . . N2 N 0.90800(14) 0.64187(14) 0.14676(9) 0.0204(2) Uani 1 1 d . . . H2 H 0.947(2) 0.750(2) 0.1595(17) 0.047(5) Uiso 1 1 d . . . N3 N 0.45926(18) 0.14933(16) -0.07107(11) 0.0344(3) Uani 1 1 d . . . N4 N 0.09859(17) -0.04434(14) 0.12640(11) 0.0311(3) Uani 1 1 d . . . N5 N 0.41053(17) 1.06787(15) 0.37520(11) 0.0329(3) Uani 1 1 d . . . N6 N 0.06355(16) 0.87030(15) 0.58321(11) 0.0288(3) Uani 1 1 d . . . C1 C 0.78027(15) 0.42405(15) 0.18998(11) 0.0182(3) Uani 1 1 d . . . C2 C 0.81346(15) 0.59438(15) 0.22751(11) 0.0181(3) Uani 1 1 d . . . C3 C 0.76109(16) 0.68258(16) 0.33191(11) 0.0214(3) Uani 1 1 d . . . H3 H 0.787(2) 0.806(2) 0.3596(14) 0.032(4) Uiso 1 1 d . . . C4 C 0.67637(17) 0.59883(17) 0.39969(11) 0.0233(3) Uani 1 1 d . . . H4 H 0.638(2) 0.659(2) 0.4744(14) 0.028(4) Uiso 1 1 d . . . C5 C 0.64505(17) 0.42925(18) 0.36224(12) 0.0237(3) Uani 1 1 d . . . H5 H 0.583(2) 0.370(2) 0.4056(14) 0.031(4) Uiso 1 1 d . . . C6 C 0.69538(16) 0.34101(17) 0.25721(11) 0.0215(3) Uani 1 1 d . . . H6 H 0.672(2) 0.219(2) 0.2309(14) 0.032(4) Uiso 1 1 d . . . C7 C 0.27216(15) 0.35503(15) 0.18038(10) 0.0168(2) Uani 1 1 d . . . C8 C 0.17424(15) 0.37656(15) 0.28031(11) 0.0179(2) Uani 1 1 d . . . H8 H 0.119(2) 0.281(2) 0.2931(14) 0.025(4) Uiso 1 1 d . . . C9 C 0.16445(16) 0.52497(15) 0.35259(11) 0.0180(2) Uani 1 1 d . . . H9 H 0.102(2) 0.543(2) 0.4210(14) 0.025(4) Uiso 1 1 d . . . C10 C 0.25220(15) 0.66608(15) 0.33229(10) 0.0173(2) Uani 1 1 d . . . C11 C 0.35022(15) 0.64445(15) 0.23247(11) 0.0180(3) Uani 1 1 d . . . H11 H 0.406(2) 0.738(2) 0.2210(14) 0.028(4) Uiso 1 1 d . . . C12 C 0.36023(15) 0.49594(15) 0.16037(11) 0.0175(2) Uani 1 1 d . . . H12 H 0.425(2) 0.481(2) 0.0926(14) 0.028(4) Uiso 1 1 d . . . C13 C 0.27798(16) 0.20369(15) 0.10492(11) 0.0184(3) Uani 1 1 d . . . C14 C 0.37804(18) 0.17492(16) 0.00691(12) 0.0229(3) Uani 1 1 d . . . C15 C 0.18040(17) 0.06567(16) 0.11841(11) 0.0214(3) Uani 1 1 d . . . C16 C 0.24294(16) 0.81873(15) 0.40647(11) 0.0194(3) Uani 1 1 d . . . C17 C 0.33465(17) 0.95796(16) 0.38892(11) 0.0227(3) Uani 1 1 d . . . C18 C 0.14390(17) 0.84636(15) 0.50482(11) 0.0214(3) Uani 1 1 d . . . B B 0.94102(18) 0.50267(18) 0.05666(13) 0.0212(3) Uani 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 0.0202(5) 0.0203(5) 0.0193(5) 0.0028(4) 0.0032(4) -0.0015(4) N2 0.0196(5) 0.0207(5) 0.0215(5) 0.0061(4) 0.0042(4) -0.0008(4) N3 0.0451(8) 0.0280(6) 0.0348(7) 0.0121(5) 0.0190(6) 0.0063(6) N4 0.0386(7) 0.0211(6) 0.0312(7) 0.0010(5) 0.0105(5) -0.0073(5) N5 0.0407(7) 0.0227(6) 0.0332(7) 0.0028(5) 0.0085(6) -0.0054(5) N6 0.0356(7) 0.0238(6) 0.0280(6) 0.0067(5) 0.0082(5) 0.0036(5) C1 0.0163(6) 0.0204(6) 0.0176(6) 0.0038(5) 0.0023(4) 0.0003(4) C2 0.0154(5) 0.0219(6) 0.0175(6) 0.0062(5) 0.0013(4) -0.0012(4) C3 0.0203(6) 0.0202(6) 0.0221(6) 0.0022(5) 0.0022(5) 0.0004(5) C4 0.0222(6) 0.0293(7) 0.0184(6) 0.0059(5) 0.0021(5) 0.0002(5) C5 0.0217(6) 0.0309(7) 0.0215(6) 0.0113(5) 0.0045(5) 0.0028(5) C6 0.0187(6) 0.0236(6) 0.0240(6) 0.0095(5) 0.0021(5) -0.0011(5) C7 0.0156(5) 0.0179(6) 0.0177(6) 0.0060(5) 0.0008(4) 0.0000(4) C8 0.0175(6) 0.0178(6) 0.0199(6) 0.0073(5) 0.0027(4) -0.0011(4) C9 0.0190(6) 0.0191(6) 0.0178(6) 0.0077(5) 0.0034(4) 0.0003(5) C10 0.0169(6) 0.0173(6) 0.0185(6) 0.0063(5) 0.0006(4) 0.0000(4) C11 0.0177(6) 0.0182(6) 0.0200(6) 0.0081(5) 0.0024(4) -0.0017(4) C12 0.0167(6) 0.0197(6) 0.0175(6) 0.0071(5) 0.0031(4) -0.0001(4) C13 0.0191(6) 0.0180(6) 0.0194(6) 0.0067(5) 0.0034(4) -0.0003(4) C14 0.0274(7) 0.0180(6) 0.0247(7) 0.0070(5) 0.0060(5) 0.0014(5) C15 0.0256(6) 0.0190(6) 0.0187(6) 0.0020(5) 0.0053(5) 0.0007(5) C16 0.0209(6) 0.0183(6) 0.0197(6) 0.0066(5) 0.0014(5) -0.0001(5) C17 0.0271(7) 0.0186(6) 0.0217(6) 0.0033(5) 0.0032(5) -0.0003(5) C18 0.0255(6) 0.0162(6) 0.0227(6) 0.0052(5) 0.0011(5) 0.0014(5) B 0.0180(7) 0.0250(7) 0.0210(7) 0.0066(6) 0.0015(5) 0.0007(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 N1 C1 1.3911(16) . ? N1 B 1.4367(18) . ? N1 H1 0.91(2) . ? N2 C2 1.3905(16) . ? N2 B 1.4312(19) . ? N2 H2 0.93(2) . ? N3 C14 1.1484(18) . ? N4 C15 1.1466(17) . ? N5 C17 1.1454(18) . ? N6 C18 1.1484(18) . ? C1 C6 1.3880(18) . ? C1 C2 1.4125(18) . ? C2 C3 1.3864(18) . ? C3 C4 1.3961(18) . ? C3 H3 1.030(17) . ? C4 C5 1.405(2) . ? C4 H4 0.988(17) . ? C5 C6 1.3869(19) . ? C5 H5 0.954(17) . ? C6 H6 1.011(17) . ? C7 C13 1.3779(17) . ? C7 C12 1.4444(17) . ? C7 C8 1.4459(17) . ? C8 C9 1.3460(18) . ? C8 H8 0.956(16) . ? C9 C10 1.4461(17) . ? C9 H9 0.968(16) . ? C10 C16 1.3829(18) . ? C10 C11 1.4452(17) . ? C11 C12 1.3460(18) . ? C11 H11 0.938(17) . ? C12 H12 0.975(16) . ? C13 C15 1.4312(17) . ? C13 C14 1.4341(18) . ? C16 C18 1.4328(19) . ? C16 C17 1.4343(18) . ? B B 1.691(3) 2_765 ? 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 B 110.08(11) . . ? C1 N1 H1 121.8(13) . . ? B N1 H1 128.1(13) . . ? C2 N2 B 110.10(11) . . ? C2 N2 H2 119.8(12) . . ? B N2 H2 129.9(12) . . ? C6 C1 N1 131.55(12) . . ? C6 C1 C2 120.70(12) . . ? N1 C1 C2 107.65(11) . . ? C3 C2 N2 131.16(12) . . ? C3 C2 C1 120.81(12) . . ? N2 C2 C1 107.94(11) . . ? C2 C3 C4 118.44(13) . . ? C2 C3 H3 120.6(9) . . ? C4 C3 H3 121.0(9) . . ? C3 C4 C5 120.43(13) . . ? C3 C4 H4 119.8(10) . . ? C5 C4 H4 119.7(10) . . ? C6 C5 C4 121.25(13) . . ? C6 C5 H5 116.9(11) . . ? C4 C5 H5 121.8(11) . . ? C5 C6 C1 118.35(13) . . ? C5 C6 H6 120.6(9) . . ? C1 C6 H6 121.1(10) . . ? C13 C7 C12 120.98(11) . . ? C13 C7 C8 120.45(11) . . ? C12 C7 C8 118.56(11) . . ? C9 C8 C7 120.66(11) . . ? C9 C8 H8 122.0(10) . . ? C7 C8 H8 117.3(10) . . ? C8 C9 C10 120.75(11) . . ? C8 C9 H9 122.4(10) . . ? C10 C9 H9 116.8(10) . . ? C16 C10 C11 120.46(11) . . ? C16 C10 C9 120.97(11) . . ? C11 C10 C9 118.57(11) . . ? C12 C11 C10 120.65(11) . . ? C12 C11 H11 122.2(10) . . ? C10 C11 H11 117.1(10) . . ? C11 C12 C7 120.81(11) . . ? C11 C12 H12 121.0(10) . . ? C7 C12 H12 118.2(10) . . ? C7 C13 C15 121.66(11) . . ? C7 C13 C14 122.54(11) . . ? C15 C13 C14 115.78(11) . . ? N3 C14 C13 178.73(14) . . ? N4 C15 C13 177.78(14) . . ? C10 C16 C18 122.30(11) . . ? C10 C16 C17 121.15(12) . . ? C18 C16 C17 116.55(11) . . ? N5 C17 C16 178.79(15) . . ? N6 C18 C16 179.05(14) . . ? N2 B N1 104.18(11) . . ? N2 B B 127.59(15) . 2_765 ? N1 B B 128.22(15) . 2_765 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N4 0.91(2) 2.48(2) 3.3048(18) 150.0(17) 2_655 N2 H2 N4 0.93(2) 2.22(2) 3.0898(17) 155.4(17) 1_665 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.451 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.052