# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Russell, Christopher' 'Mansell, Stephen' 'Adams, Christopher' 'Bramham, George' 'Haddow, Mairi' 'Norman, Nicholas' 'Udeen, Sally' 'Kaim, W.' 'McGrady, John' _publ_contact_author_name 'Russell, Christopher' _publ_contact_author_email Chris.Russell@bristol.ac.uk _publ_section_title ; Synthesis and Characterisation of the Persistent Neutral Boron-Containing Radical [BCl2(bipy)](bipy = 2,2'-bipyridyl) ; # Attachment 'Merged.cif.txt' data_3 _database_code_depnum_ccdc_archive 'CCDC 768026' #TrackingRef 'Merged.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H8 B Cl2 N2' _chemical_formula_sum 'C10 H8 B Cl2 N2' _chemical_formula_weight 237.89 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' Cl Cl 0.1484 0.1585 '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 6.8993(5) _cell_length_b 8.7488(6) _cell_length_c 9.2777(7) _cell_angle_alpha 68.821(4) _cell_angle_beta 80.171(4) _cell_angle_gamma 88.519(4) _cell_volume 514.13(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1777 _cell_measurement_theta_min 3.50 _cell_measurement_theta_max 27.48 _exptl_crystal_description rod _exptl_crystal_colour purple _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 242 _exptl_absorpt_coefficient_mu 0.592 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.858 _exptl_absorpt_correction_T_max 0.965 _exptl_absorpt_process_details 'TWINABS V2008/1' _exptl_special_details ; The crystal was a twin, for which the two components were rotated around the c-axis by x degrees. The data were integrated using two components and refined using HKLF 5 to show the component was present in a 0.53/0.47 ratio. ; _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 '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 2347 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 27.51 _reflns_number_total 2347 _reflns_number_gt 2099 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II' _computing_cell_refinement 'Bruker Apex II' _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^)+(0.0427P)^2^+0.3221P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2347 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0895 _refine_ls_wR_factor_gt 0.0750 _refine_ls_goodness_of_fit_ref 1.142 _refine_ls_restrained_S_all 1.142 _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 Cl1 Cl 0.08403(8) 0.26014(7) 0.24910(7) 0.01804(15) Uani 1 1 d . . . Cl2 Cl 0.51468(8) 0.23490(7) 0.27498(7) 0.01700(14) Uani 1 1 d . . . N1 N 0.2280(3) 0.2787(2) 0.5110(2) 0.0141(4) Uani 1 1 d . . . N2 N 0.2982(3) 0.5110(2) 0.2860(2) 0.0133(4) Uani 1 1 d . . . B1 B 0.2783(4) 0.3252(3) 0.3339(3) 0.0138(5) Uani 1 1 d . . . C1 C 0.1863(4) 0.1272(3) 0.6224(3) 0.0165(5) Uani 1 1 d . . . H1 H 0.1819 0.0370 0.5923 0.020 Uiso 1 1 calc R . . C2 C 0.1507(4) 0.1051(3) 0.7776(3) 0.0181(5) Uani 1 1 d . . . H2 H 0.1211 0.0007 0.8529 0.022 Uiso 1 1 calc R . . C3 C 0.1592(4) 0.2424(3) 0.8239(3) 0.0181(5) Uani 1 1 d . . . H3 H 0.1365 0.2278 0.9298 0.022 Uiso 1 1 calc R . . C4 C 0.2006(4) 0.3963(3) 0.7124(3) 0.0159(5) Uani 1 1 d . . . H4 H 0.2061 0.4869 0.7418 0.019 Uiso 1 1 calc R . . C5 C 0.2346(4) 0.4154(3) 0.5537(3) 0.0135(5) Uani 1 1 d . . . C6 C 0.2760(3) 0.5570(3) 0.4161(3) 0.0130(5) Uani 1 1 d . . . C7 C 0.2916(4) 0.7233(3) 0.3956(3) 0.0153(5) Uani 1 1 d . . . H7 H 0.2761 0.7550 0.4823 0.018 Uiso 1 1 calc R . . C8 C 0.3301(3) 0.8387(3) 0.2466(3) 0.0167(5) Uani 1 1 d . . . H8 H 0.3403 0.9494 0.2314 0.020 Uiso 1 1 calc R . . C9 C 0.3541(4) 0.7880(3) 0.1157(3) 0.0172(5) Uani 1 1 d . . . H9 H 0.3817 0.8656 0.0144 0.021 Uiso 1 1 calc R . . C10 C 0.3369(4) 0.6257(3) 0.1386(3) 0.0158(5) Uani 1 1 d . . . H10 H 0.3517 0.5932 0.0525 0.019 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 Cl1 0.0191(3) 0.0183(3) 0.0203(3) -0.0102(2) -0.0055(2) -0.0009(2) Cl2 0.0174(3) 0.0166(3) 0.0185(3) -0.0089(2) -0.0020(2) 0.0033(2) N1 0.0144(10) 0.0128(9) 0.0162(10) -0.0064(8) -0.0026(8) 0.0013(8) N2 0.0142(10) 0.0123(9) 0.0149(10) -0.0065(8) -0.0028(8) 0.0002(8) B1 0.0164(12) 0.0115(12) 0.0152(13) -0.0068(9) -0.0033(10) 0.0003(9) C1 0.0173(11) 0.0117(10) 0.0194(12) -0.0040(9) -0.0036(9) 0.0001(9) C2 0.0181(12) 0.0147(11) 0.0184(12) -0.0020(10) -0.0036(10) -0.0005(9) C3 0.0144(12) 0.0250(13) 0.0139(11) -0.0066(10) -0.0006(9) 0.0014(9) C4 0.0148(11) 0.0176(12) 0.0183(12) -0.0100(10) -0.0036(9) 0.0013(9) C5 0.0113(11) 0.0132(11) 0.0177(12) -0.0073(9) -0.0035(9) 0.0022(8) C6 0.0101(10) 0.0151(11) 0.0150(11) -0.0072(9) -0.0013(8) 0.0015(8) C7 0.0134(11) 0.0153(11) 0.0204(13) -0.0095(10) -0.0046(10) 0.0008(9) C8 0.0144(12) 0.0136(11) 0.0236(13) -0.0081(10) -0.0040(10) 0.0004(9) C9 0.0172(12) 0.0134(11) 0.0180(12) -0.0020(9) -0.0029(9) -0.0003(9) C10 0.0170(12) 0.0158(11) 0.0150(11) -0.0059(9) -0.0034(9) 0.0007(9) _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 Cl1 B1 1.861(3) . ? Cl2 B1 1.878(3) . ? N1 C1 1.355(3) . ? N1 C5 1.393(3) . ? N1 B1 1.522(3) . ? N2 C10 1.359(3) . ? N2 C6 1.388(3) . ? N2 B1 1.525(3) . ? C1 C2 1.361(4) . ? C1 H1 0.9300 . ? C2 C3 1.419(4) . ? C2 H2 0.9300 . ? C3 C4 1.371(3) . ? C3 H3 0.9300 . ? C4 C5 1.399(3) . ? C4 H4 0.9300 . ? C5 C6 1.413(3) . ? C6 C7 1.402(3) . ? C7 C8 1.372(3) . ? C7 H7 0.9300 . ? C8 C9 1.419(4) . ? C8 H8 0.9300 . ? C9 C10 1.363(3) . ? C9 H9 0.9300 . ? C10 H10 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 C1 N1 C5 120.4(2) . . ? C1 N1 B1 128.1(2) . . ? C5 N1 B1 111.52(19) . . ? C10 N2 C6 120.6(2) . . ? C10 N2 B1 127.9(2) . . ? C6 N2 B1 111.50(19) . . ? N2 B1 N1 98.92(16) . . ? N2 B1 Cl1 112.94(18) . . ? N1 B1 Cl1 113.49(18) . . ? N2 B1 Cl2 112.21(18) . . ? N1 B1 Cl2 111.58(18) . . ? Cl1 B1 Cl2 107.65(11) . . ? N1 C1 C2 121.0(2) . . ? N1 C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? C1 C2 C3 119.6(2) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 120.0(2) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 119.1(2) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? N1 C5 C4 119.9(2) . . ? N1 C5 C6 108.8(2) . . ? C4 C5 C6 131.3(2) . . ? N2 C6 C7 119.9(2) . . ? N2 C6 C5 109.1(2) . . ? C7 C6 C5 131.0(2) . . ? C8 C7 C6 119.4(2) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C7 C8 C9 119.6(2) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 120.0(2) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? N2 C10 C9 120.7(2) . . ? N2 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? 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 C10 N2 B1 N1 -177.8(2) . . . . ? C6 N2 B1 N1 3.6(3) . . . . ? C10 N2 B1 Cl1 -57.5(3) . . . . ? C6 N2 B1 Cl1 123.90(19) . . . . ? C10 N2 B1 Cl2 64.4(3) . . . . ? C6 N2 B1 Cl2 -114.20(19) . . . . ? C1 N1 B1 N2 177.9(2) . . . . ? C5 N1 B1 N2 -4.0(3) . . . . ? C1 N1 B1 Cl1 58.0(3) . . . . ? C5 N1 B1 Cl1 -123.94(18) . . . . ? C1 N1 B1 Cl2 -63.8(3) . . . . ? C5 N1 B1 Cl2 114.22(19) . . . . ? C5 N1 C1 C2 -0.2(4) . . . . ? B1 N1 C1 C2 177.7(2) . . . . ? N1 C1 C2 C3 -0.6(4) . . . . ? C1 C2 C3 C4 0.8(4) . . . . ? C2 C3 C4 C5 -0.1(4) . . . . ? C1 N1 C5 C4 0.9(3) . . . . ? B1 N1 C5 C4 -177.3(2) . . . . ? C1 N1 C5 C6 -178.6(2) . . . . ? B1 N1 C5 C6 3.2(3) . . . . ? C3 C4 C5 N1 -0.7(4) . . . . ? C3 C4 C5 C6 178.6(2) . . . . ? C10 N2 C6 C7 0.6(3) . . . . ? B1 N2 C6 C7 179.3(2) . . . . ? C10 N2 C6 C5 179.3(2) . . . . ? B1 N2 C6 C5 -2.0(3) . . . . ? N1 C5 C6 N2 -0.7(2) . . . . ? C4 C5 C6 N2 179.9(3) . . . . ? N1 C5 C6 C7 177.7(3) . . . . ? C4 C5 C6 C7 -1.6(4) . . . . ? N2 C6 C7 C8 -0.4(3) . . . . ? C5 C6 C7 C8 -178.7(2) . . . . ? C6 C7 C8 C9 -0.3(3) . . . . ? C7 C8 C9 C10 0.7(4) . . . . ? C6 N2 C10 C9 -0.2(4) . . . . ? B1 N2 C10 C9 -178.6(2) . . . . ? C8 C9 C10 N2 -0.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.350 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.080 #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 768027' #TrackingRef 'Merged.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H8 B Cl2 N2, Cl' _chemical_formula_sum 'C10 H8 B Cl3 N2' _chemical_formula_weight 273.34 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnma _symmetry_space_group_name_Hall '-P 2ac 2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 14.218(3) _cell_length_b 6.7301(13) _cell_length_c 12.211(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1168.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6682 _cell_measurement_theta_min 2.1985 _cell_measurement_theta_max 30.113 _exptl_crystal_description Rod _exptl_crystal_colour COlourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.753 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.730026 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS - Bruker V2.05' _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 'Bruker Kappa-APEX-II area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8101 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0188 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1448 _reflns_number_gt 1396 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX-II (Bruker, 2004)' _computing_cell_refinement 'APEX-II and SAINT (Bruker, 2001)' _computing_data_reduction 'SAINT v7.51A (BRUKER)' _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^)+(0.0460P)^2^+0.8427P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1448 _refine_ls_number_parameters 94 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0253 _refine_ls_R_factor_gt 0.0240 _refine_ls_wR_factor_ref 0.0775 _refine_ls_wR_factor_gt 0.0704 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 B1 B 0.18555(14) 0.2500 0.46059(16) 0.0130(4) Uani 1 2 d S . . Cl1 Cl 0.11301(2) 0.02793(5) 0.45613(2) 0.01635(13) Uani 1 1 d . . . Cl2 Cl 0.14635(3) 0.2500 0.99344(4) 0.01890(14) Uani 1 2 d S . . N1 N 0.25251(11) 0.2500 0.56148(13) 0.0124(3) Uani 1 2 d S . . N2 N 0.26298(11) 0.2500 0.36998(12) 0.0121(3) Uani 1 2 d S . . C1 C 0.22648(13) 0.2500 0.66758(15) 0.0148(4) Uani 1 2 d S . . H1 H 0.1616 0.2500 0.6864 0.018 Uiso 1 2 calc SR . . C2 C 0.29339(14) 0.2500 0.74855(16) 0.0166(4) Uani 1 2 d S . . H2 H 0.2756 0.2500 0.8235 0.020 Uiso 1 2 calc SR . . C3 C 0.38805(13) 0.2500 0.71861(16) 0.0170(4) Uani 1 2 d S . . H3 H 0.4350 0.2500 0.7739 0.020 Uiso 1 2 calc SR . . C4 C 0.41460(13) 0.2500 0.60945(16) 0.0155(4) Uani 1 2 d S . . H4 H 0.4790 0.2500 0.5886 0.019 Uiso 1 2 calc SR . . C5 C 0.34382(13) 0.2500 0.53252(15) 0.0127(4) Uani 1 2 d S . . C6 C 0.35058(12) 0.2500 0.41303(15) 0.0131(4) Uani 1 2 d S . . C7 C 0.42964(13) 0.2500 0.34792(16) 0.0161(4) Uani 1 2 d S . . H7 H 0.4910 0.2500 0.3788 0.019 Uiso 1 2 calc SR . . C8 C 0.41595(14) 0.2500 0.23493(16) 0.0180(4) Uani 1 2 d S . . H8 H 0.4688 0.2500 0.1873 0.022 Uiso 1 2 calc SR . . C9 C 0.32541(14) 0.2500 0.19112(15) 0.0166(4) Uani 1 2 d S . . H9 H 0.3163 0.2500 0.1141 0.020 Uiso 1 2 calc SR . . C10 C 0.24925(13) 0.2500 0.26108(15) 0.0144(4) Uani 1 2 d S . . H10 H 0.1872 0.2500 0.2323 0.017 Uiso 1 2 calc SR . . 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 0.0116(9) 0.0187(10) 0.0087(9) 0.000 0.0008(7) 0.000 Cl1 0.01407(19) 0.0213(2) 0.01370(19) 0.00028(11) 0.00025(10) -0.00406(12) Cl2 0.0133(2) 0.0236(3) 0.0198(3) 0.000 -0.00002(16) 0.000 N1 0.0119(7) 0.0159(7) 0.0093(7) 0.000 0.0000(5) 0.000 N2 0.0120(7) 0.0151(7) 0.0091(7) 0.000 0.0016(5) 0.000 C1 0.0149(8) 0.0188(9) 0.0105(8) 0.000 0.0030(7) 0.000 C2 0.0205(9) 0.0194(9) 0.0099(8) 0.000 0.0016(7) 0.000 C3 0.0179(9) 0.0207(9) 0.0125(9) 0.000 -0.0033(7) 0.000 C4 0.0145(8) 0.0182(9) 0.0138(8) 0.000 -0.0006(7) 0.000 C5 0.0135(8) 0.0146(8) 0.0100(8) 0.000 0.0019(6) 0.000 C6 0.0135(8) 0.0148(8) 0.0110(8) 0.000 -0.0002(6) 0.000 C7 0.0133(8) 0.0206(9) 0.0145(9) 0.000 0.0023(7) 0.000 C8 0.0187(9) 0.0213(9) 0.0141(9) 0.000 0.0053(7) 0.000 C9 0.0222(9) 0.0183(9) 0.0093(8) 0.000 0.0028(7) 0.000 C10 0.0168(8) 0.0161(8) 0.0104(8) 0.000 -0.0004(7) 0.000 _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 N1 1.557(2) . ? B1 N2 1.561(2) . ? B1 Cl1 1.8167(13) . ? B1 Cl1 1.8167(13) 7_565 ? N1 C5 1.346(2) . ? N1 C1 1.347(2) . ? N2 C10 1.344(2) . ? N2 C6 1.352(2) . ? C1 C2 1.372(3) . ? C1 H1 0.9500 . ? C2 C3 1.395(3) . ? C2 H2 0.9500 . ? C3 C4 1.385(3) . ? C3 H3 0.9500 . ? C4 C5 1.377(3) . ? C4 H4 0.9500 . ? C5 C6 1.462(2) . ? C6 C7 1.377(3) . ? C7 C8 1.393(3) . ? C7 H7 0.9500 . ? C8 C9 1.394(3) . ? C8 H8 0.9500 . ? C9 C10 1.379(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? 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 N1 B1 N2 97.45(14) . . ? N1 B1 Cl1 111.77(8) . . ? N2 B1 Cl1 112.28(8) . . ? N1 B1 Cl1 111.77(8) . 7_565 ? N2 B1 Cl1 112.29(8) . 7_565 ? Cl1 B1 Cl1 110.70(11) . 7_565 ? C5 N1 C1 121.18(16) . . ? C5 N1 B1 112.46(15) . . ? C1 N1 B1 126.36(16) . . ? C10 N2 C6 121.24(16) . . ? C10 N2 B1 126.79(16) . . ? C6 N2 B1 111.97(15) . . ? N1 C1 C2 120.16(17) . . ? N1 C1 H1 119.9 . . ? C2 C1 H1 119.9 . . ? C1 C2 C3 118.70(18) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 121.01(18) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C5 C4 C3 117.22(17) . . ? C5 C4 H4 121.4 . . ? C3 C4 H4 121.4 . . ? N1 C5 C4 121.74(17) . . ? N1 C5 C6 109.00(16) . . ? C4 C5 C6 129.26(17) . . ? N2 C6 C7 121.84(17) . . ? N2 C6 C5 109.12(15) . . ? C7 C6 C5 129.04(17) . . ? C6 C7 C8 117.24(18) . . ? C6 C7 H7 121.4 . . ? C8 C7 H7 121.4 . . ? C7 C8 C9 120.60(18) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C10 C9 C8 119.17(18) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? N2 C10 C9 119.91(17) . . ? N2 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? 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 C5 0.0 . . . . ? Cl1 B1 N1 C5 117.65(9) . . . . ? Cl1 B1 N1 C5 -117.65(9) 7_565 . . . ? N2 B1 N1 C1 180.0 . . . . ? Cl1 B1 N1 C1 -62.35(9) . . . . ? Cl1 B1 N1 C1 62.35(9) 7_565 . . . ? N1 B1 N2 C10 180.0 . . . . ? Cl1 B1 N2 C10 62.75(9) . . . . ? Cl1 B1 N2 C10 -62.76(9) 7_565 . . . ? N1 B1 N2 C6 0.0 . . . . ? Cl1 B1 N2 C6 -117.25(9) . . . . ? Cl1 B1 N2 C6 117.24(9) 7_565 . . . ? C5 N1 C1 C2 0.0 . . . . ? B1 N1 C1 C2 180.0 . . . . ? N1 C1 C2 C3 0.0 . . . . ? C1 C2 C3 C4 0.0 . . . . ? C2 C3 C4 C5 0.0 . . . . ? C1 N1 C5 C4 0.0 . . . . ? B1 N1 C5 C4 180.0 . . . . ? C1 N1 C5 C6 180.0 . . . . ? B1 N1 C5 C6 0.0 . . . . ? C3 C4 C5 N1 0.0 . . . . ? C3 C4 C5 C6 180.0 . . . . ? C10 N2 C6 C7 0.0 . . . . ? B1 N2 C6 C7 180.0 . . . . ? C10 N2 C6 C5 180.0 . . . . ? B1 N2 C6 C5 0.0 . . . . ? N1 C5 C6 N2 0.0 . . . . ? C4 C5 C6 N2 180.0 . . . . ? N1 C5 C6 C7 180.0 . . . . ? C4 C5 C6 C7 0.0 . . . . ? N2 C6 C7 C8 0.0 . . . . ? C5 C6 C7 C8 180.0 . . . . ? C6 C7 C8 C9 0.0 . . . . ? C7 C8 C9 C10 0.0 . . . . ? C6 N2 C10 C9 0.0 . . . . ? B1 N2 C10 C9 180.0 . . . . ? C8 C9 C10 N2 0.0 . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.364 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.058