# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Shih-Yuan Liu' _publ_contact_author_email LSY@UOREGON.EDU _publ_section_title ; BN benzonitrile: an electron-deficient 1,2-dihydro-1,2-azaborine featuring linkage isomerism ; loop_ _publ_author_name 'Shih-Yuan Liu.' 'Adam J. V. Marwitz' 'Sean P McClintock' 'Lev N. Zakharov' # Attachment 'Cif_file.cif' data_liu12a _database_code_depnum_ccdc_archive 'CCDC 748502' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H9 B Cr N2 O5' _chemical_formula_weight 324.02 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' 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' Cr Cr 0.3209 0.6236 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 12.965(2) _cell_length_b 5.9808(9) _cell_length_c 19.254(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1493.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1659 _cell_measurement_theta_min 3.32 _cell_measurement_theta_max 22.28 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.785 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8400 _exptl_absorpt_correction_T_max 0.9544 _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 9061 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0520 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3243 _reflns_number_gt 2639 _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^)+(0.0364P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.20(3) _refine_ls_number_reflns 3243 _refine_ls_number_parameters 191 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0390 _refine_ls_wR_factor_ref 0.0864 _refine_ls_wR_factor_gt 0.0778 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 Cr1 Cr 0.66574(3) 0.74296(7) 0.97759(4) 0.02551(12) Uani 1 1 d . . . O1 O 0.7486(2) 0.3932(4) 0.87751(14) 0.0554(7) Uani 1 1 d . . . O2 O 0.46225(18) 0.4941(4) 0.99396(12) 0.0448(6) Uani 1 1 d . . . O3 O 0.5789(2) 1.1017(4) 1.07256(13) 0.0481(7) Uani 1 1 d . . . O4 O 0.86623(18) 1.0056(4) 0.9693(2) 0.0632(8) Uani 1 1 d . . . O5 O 0.7561(2) 0.4899(4) 1.09899(13) 0.0519(7) Uani 1 1 d . . . N1 N 0.5758(2) 1.0066(4) 0.85059(13) 0.0348(7) Uani 1 1 d . . . N2 N 0.57268(19) 1.1203(4) 0.72643(12) 0.0300(6) Uani 1 1 d . . . B1 B 0.5390(3) 1.1603(6) 0.79504(18) 0.0314(8) Uani 1 1 d . . . C1 C 0.7175(3) 0.5237(5) 0.91526(17) 0.0333(8) Uani 1 1 d . . . C2 C 0.5388(2) 0.5846(5) 0.98694(16) 0.0297(7) Uani 1 1 d . . . C3 C 0.6121(3) 0.9656(5) 1.03706(17) 0.0318(8) Uani 1 1 d . . . C4 C 0.7910(2) 0.9078(5) 0.9713(2) 0.0376(8) Uani 1 1 d . . . C5 C 0.7216(3) 0.5855(6) 1.05295(18) 0.0344(8) Uani 1 1 d . . . C6 C 0.6086(2) 0.9084(5) 0.89718(17) 0.0289(7) Uani 1 1 d . . . C7 C 0.4700(3) 1.3536(6) 0.80883(17) 0.0412(8) Uani 1 1 d . . . H7A H 0.4436 1.3831 0.8539 0.049 Uiso 1 1 calc R . . C8 C 0.4463(3) 1.4870(6) 0.7534(2) 0.0473(10) Uani 1 1 d . . . H8A H 0.4033 1.6137 0.7603 0.057 Uiso 1 1 calc R . . C9 C 0.4837(3) 1.4417(6) 0.68671(18) 0.0429(9) Uani 1 1 d . . . H9A H 0.4655 1.5374 0.6493 0.051 Uiso 1 1 calc R . . C10 C 0.5449(3) 1.2648(5) 0.67488(17) 0.0363(8) Uani 1 1 d . . . H10A H 0.5697 1.2393 0.6291 0.044 Uiso 1 1 calc R . . C11 C 0.6445(3) 0.9368(6) 0.70745(18) 0.0402(8) Uani 1 1 d . . . H11A H 0.6328 0.8938 0.6584 0.048 Uiso 1 1 calc R . . H11B H 0.6301 0.8046 0.7368 0.048 Uiso 1 1 calc R . . C12 C 0.7559(3) 1.0065(6) 0.7169(2) 0.0454(9) Uani 1 1 d . . . H12A H 0.8013 0.8818 0.7043 0.068 Uiso 1 1 calc R . . H12B H 0.7678 1.0477 0.7655 0.068 Uiso 1 1 calc R . . H12C H 0.7708 1.1350 0.6870 0.068 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 Cr1 0.0220(2) 0.0253(2) 0.0293(2) 0.00447(19) -0.0022(3) -0.00095(18) O1 0.0493(17) 0.0456(15) 0.0713(19) -0.0156(14) 0.0148(15) -0.0042(13) O2 0.0304(14) 0.0484(13) 0.0557(17) 0.0017(11) 0.0004(12) -0.0111(11) O3 0.0575(19) 0.0379(14) 0.0489(15) -0.0081(12) 0.0001(13) 0.0060(12) O4 0.0342(14) 0.0505(14) 0.105(2) 0.0139(17) -0.0059(18) -0.0130(12) O5 0.0416(17) 0.0621(17) 0.0520(16) 0.0255(13) -0.0116(13) 0.0053(13) N1 0.0308(17) 0.0429(16) 0.0308(14) 0.0053(13) 0.0019(13) -0.0004(14) N2 0.0273(15) 0.0315(15) 0.0313(14) 0.0020(11) -0.0028(12) -0.0042(12) B1 0.030(2) 0.0351(19) 0.0294(18) 0.0040(15) -0.0051(16) -0.0033(17) C1 0.026(2) 0.0284(18) 0.045(2) 0.0042(15) 0.0034(15) -0.0027(15) C2 0.0334(17) 0.0291(15) 0.0264(16) 0.0025(13) -0.0046(16) 0.0034(13) C3 0.030(2) 0.0304(18) 0.0348(18) 0.0068(15) -0.0057(15) -0.0021(15) C4 0.0296(17) 0.0300(15) 0.053(2) 0.0082(18) -0.001(2) -0.0005(13) C5 0.029(2) 0.0348(18) 0.039(2) 0.0034(15) -0.0029(16) -0.0055(15) C6 0.0219(18) 0.0337(17) 0.0310(16) 0.0022(14) 0.0038(15) -0.0006(14) C7 0.036(2) 0.053(2) 0.0347(18) -0.0037(15) -0.0017(15) 0.0071(18) C8 0.040(2) 0.040(2) 0.061(2) 0.0056(18) -0.0112(19) 0.0099(18) C9 0.043(2) 0.042(2) 0.044(2) 0.0139(16) -0.0145(17) -0.0101(18) C10 0.0357(19) 0.046(2) 0.0272(16) 0.0065(14) -0.0062(14) -0.0111(17) C11 0.044(2) 0.0341(18) 0.0420(19) -0.0062(15) 0.0050(17) 0.0016(17) C12 0.0333(19) 0.0510(19) 0.052(2) 0.0017(17) 0.0068(18) 0.005(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 Cr1 C5 1.875(4) . ? Cr1 C3 1.889(4) . ? Cr1 C1 1.900(4) . ? Cr1 C4 1.904(3) . ? Cr1 C2 1.908(3) . ? Cr1 C6 1.981(3) . ? O1 C1 1.141(4) . ? O2 C2 1.138(3) . ? O3 C3 1.147(4) . ? O4 C4 1.138(3) . ? O5 C5 1.146(4) . ? N1 C6 1.153(4) . ? N1 B1 1.489(4) . ? N2 C10 1.365(4) . ? N2 B1 1.412(4) . ? N2 C11 1.484(4) . ? B1 C7 1.486(5) . ? C7 C8 1.368(5) . ? C7 H7A 0.9500 . ? C8 C9 1.399(5) . ? C8 H8A 0.9500 . ? C9 C10 1.342(5) . ? C9 H9A 0.9500 . ? C10 H10A 0.9500 . ? C11 C12 1.514(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 Cr1 C3 91.55(15) . . ? C5 Cr1 C1 90.33(14) . . ? C3 Cr1 C1 178.11(16) . . ? C5 Cr1 C4 88.83(16) . . ? C3 Cr1 C4 89.27(15) . . ? C1 Cr1 C4 90.92(15) . . ? C5 Cr1 C2 90.62(14) . . ? C3 Cr1 C2 88.58(14) . . ? C1 Cr1 C2 91.24(14) . . ? C4 Cr1 C2 177.77(17) . . ? C5 Cr1 C6 179.16(16) . . ? C3 Cr1 C6 89.07(13) . . ? C1 Cr1 C6 89.04(14) . . ? C4 Cr1 C6 90.62(14) . . ? C2 Cr1 C6 89.95(13) . . ? C6 N1 B1 172.4(3) . . ? C10 N2 B1 119.4(3) . . ? C10 N2 C11 117.0(3) . . ? B1 N2 C11 123.3(3) . . ? N2 B1 N1 117.9(3) . . ? N2 B1 C7 119.0(3) . . ? N1 B1 C7 123.0(3) . . ? O1 C1 Cr1 179.5(3) . . ? O2 C2 Cr1 178.1(3) . . ? O3 C3 Cr1 179.2(3) . . ? O4 C4 Cr1 178.3(4) . . ? O5 C5 Cr1 179.7(4) . . ? N1 C6 Cr1 179.3(3) . . ? C8 C7 B1 116.7(3) . . ? C8 C7 H7A 121.6 . . ? B1 C7 H7A 121.6 . . ? C7 C8 C9 121.7(3) . . ? C7 C8 H8A 119.2 . . ? C9 C8 H8A 119.2 . . ? C10 C9 C8 120.9(3) . . ? C10 C9 H9A 119.5 . . ? C8 C9 H9A 119.5 . . ? C9 C10 N2 122.1(3) . . ? C9 C10 H10A 118.9 . . ? N2 C10 H10A 118.9 . . ? N2 C11 C12 111.4(3) . . ? N2 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? N2 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.301 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.058