Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Alan H. Cowley' _publ_contact_author_address ; Department of Chemistry and Biochemistry University of Texas-Austin 1 University Station, A5300 Austin, TX 78701 USA ; _publ_contact_author_phone 512-471-7484 _publ_contact_author_fax 512-471-6822 _publ_contact_author_email cowley@mail.utexas.edu _publ_section_title ; Synthetic and structural chemistry of amidinate-substituted boron halides ; loop_ _publ_author_name _publ_author_address 'Nicholas J. Hill' ; Department of Chemistry and Biochemistry University of Texas-Austin 1 University Station, A5300 Austin, TX 78701 USA ; 'Michael Findlater' ; Department of Chemistry and Biochemistry University of Texas-Austin 1 University Station, A5300 Austin, TX 78701 USA ; 'Alan H. Cowley' ; Department of Chemistry and Biochemistry University of Texas-Austin 1 University Station, A5300 Austin, TX 78701 USA ; _publ_section_synopsis ; ; _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_references ; Allen, F.H. (2002). Acta Cryst. B58, 380-388. Cremer D. & Pople J.A. (1975). J. Am. Chem. Soc. 97, 1358-1367. Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. ; _publ_section_figure_captions ; ; _publ_section_exptl_prep ; ; data_NHNH017 _database_code_depnum_ccdc_archive 'CCDC 275321' _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; _publ_section_references ; Allen, F.H. (2002). Acta Cryst. B58, 380-388. Cremer D. & Pople J.A. (1975). J. Am. Chem. Soc. 97, 1358-1367. Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. ; _publ_section_figure_captions ; ; _publ_section_exptl_prep ; ; #3. data _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H25 B Cl2 N2' _chemical_formula_sum 'C14 H25 B Cl2 N2' _chemical_formula_weight 303.07 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 monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall -P2yn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.590(5) _cell_length_b 7.324(5) _cell_length_c 16.451(5) _cell_angle_alpha 90 _cell_angle_beta 94.622(5) _cell_angle_gamma 90 _cell_volume 1632.1(14) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.387 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9061 _exptl_absorpt_correction_T_max 0.9336 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6930 _diffrn_reflns_av_R_equivalents 0.0584 _diffrn_reflns_av_sigmaI/netI 0.0945 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3739 _reflns_number_gt 1976 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement Denzo _computing_data_reduction Scalepack _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0630P)^2^+0.0041P] 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 3739 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1284 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1309 _refine_ls_wR_factor_gt 0.1045 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.973 _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 C1 C 0.33382(16) 0.6306(3) -0.05351(14) 0.0279(6) Uani 1 1 d . . . C2 C 0.37112(18) 0.8104(3) -0.07806(15) 0.0337(6) Uani 1 1 d . . . H2A H 0.4409 0.8172 -0.0638 0.051 Uiso 1 1 calc R . . H2B H 0.3384 0.9054 -0.0504 0.051 Uiso 1 1 calc R . . H2C H 0.3583 0.8254 -0.1359 0.051 Uiso 1 1 calc R . . C3 C 0.23735(17) 0.7064(3) 0.06767(14) 0.0282(6) Uani 1 1 d . . . H3 H 0.2851 0.8036 0.0822 0.034 Uiso 1 1 calc R . . C4 C 0.14089(19) 0.7954(4) 0.03578(16) 0.0377(7) Uani 1 1 d . . . H4A H 0.0932 0.7015 0.0189 0.045 Uiso 1 1 calc R . . H4B H 0.1519 0.8697 -0.0115 0.045 Uiso 1 1 calc R . . C5 C 0.09989(19) 0.9142(4) 0.10109(15) 0.0437(7) Uani 1 1 d . . . H5A H 0.1446 1.0152 0.1141 0.052 Uiso 1 1 calc R . . H5B H 0.0367 0.9643 0.0804 0.052 Uiso 1 1 calc R . . C6 C 0.0869(2) 0.8038(4) 0.17813(16) 0.0436(7) Uani 1 1 d . . . H6A H 0.0647 0.8837 0.2200 0.052 Uiso 1 1 calc R . . H6B H 0.0368 0.7110 0.1665 0.052 Uiso 1 1 calc R . . C7 C 0.1827(2) 0.7139(3) 0.20910(15) 0.0389(7) Uani 1 1 d . . . H7A H 0.1716 0.6391 0.2562 0.047 Uiso 1 1 calc R . . H7B H 0.2306 0.8071 0.2263 0.047 Uiso 1 1 calc R . . C8 C 0.22373(18) 0.5956(3) 0.14392(13) 0.0321(6) Uani 1 1 d . . . H8A H 0.2867 0.5448 0.1647 0.039 Uiso 1 1 calc R . . H8B H 0.1789 0.4951 0.1305 0.039 Uiso 1 1 calc R . . C9 C 0.39551(16) 0.4140(3) -0.15795(13) 0.0299(6) Uani 1 1 d . . . H9 H 0.4248 0.5236 -0.1802 0.036 Uiso 1 1 calc R . . C10 C 0.47796(17) 0.2792(3) -0.13549(15) 0.0352(6) Uani 1 1 d . . . H10A H 0.4511 0.1744 -0.1088 0.042 Uiso 1 1 calc R . . H10B H 0.5265 0.3363 -0.0971 0.042 Uiso 1 1 calc R . . C11 C 0.52884(19) 0.2142(4) -0.20992(16) 0.0400(7) Uani 1 1 d . . . H11A H 0.5648 0.3152 -0.2315 0.048 Uiso 1 1 calc R . . H11B H 0.5760 0.1192 -0.1934 0.048 Uiso 1 1 calc R . . C12 C 0.45488(19) 0.1407(4) -0.27625(15) 0.0410(7) Uani 1 1 d . . . H12A H 0.4888 0.1119 -0.3243 0.049 Uiso 1 1 calc R . . H12B H 0.4259 0.0289 -0.2574 0.049 Uiso 1 1 calc R . . C13 C 0.3743(2) 0.2770(4) -0.29847(16) 0.0461(8) Uani 1 1 d . . . H13A H 0.3264 0.2235 -0.3384 0.055 Uiso 1 1 calc R . . H13B H 0.4023 0.3836 -0.3229 0.055 Uiso 1 1 calc R . . C14 C 0.32258(19) 0.3349(4) -0.22328(15) 0.0408(7) Uani 1 1 d . . . H14A H 0.2725 0.4254 -0.2390 0.049 Uiso 1 1 calc R . . H14B H 0.2900 0.2299 -0.2015 0.049 Uiso 1 1 calc R . . B1 B 0.2820(2) 0.3852(4) -0.01987(17) 0.0315(7) Uani 1 1 d . . . N1 N 0.27877(14) 0.5892(2) 0.00714(11) 0.0280(5) Uani 1 1 d . . . N2 N 0.34627(14) 0.4671(3) -0.08624(11) 0.0295(5) Uani 1 1 d . . . Cl1 Cl 0.16439(5) 0.28522(10) -0.05732(4) 0.0500(2) Uani 1 1 d . . . Cl2 Cl 0.35030(5) 0.23292(9) 0.05424(4) 0.0402(2) 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 C1 0.0285(13) 0.0288(14) 0.0259(13) 0.0002(11) -0.0008(11) 0.0012(11) C2 0.0406(15) 0.0279(14) 0.0330(15) -0.0001(12) 0.0057(12) -0.0034(12) C3 0.0337(14) 0.0249(13) 0.0267(14) -0.0042(10) 0.0062(11) -0.0011(10) C4 0.0394(15) 0.0414(16) 0.0324(15) 0.0015(12) 0.0028(12) 0.0089(12) C5 0.0430(16) 0.0403(16) 0.0488(18) -0.0025(14) 0.0100(14) 0.0068(13) C6 0.0516(18) 0.0336(15) 0.0483(18) -0.0056(13) 0.0214(14) 0.0004(13) C7 0.0529(16) 0.0363(15) 0.0293(15) -0.0017(12) 0.0144(12) -0.0017(13) C8 0.0375(14) 0.0314(14) 0.0279(14) -0.0005(11) 0.0048(11) 0.0006(11) C9 0.0354(14) 0.0290(14) 0.0261(14) 0.0006(11) 0.0076(11) -0.0025(11) C10 0.0335(14) 0.0381(15) 0.0336(15) -0.0030(12) 0.0000(11) 0.0026(12) C11 0.0346(15) 0.0446(17) 0.0411(17) -0.0048(13) 0.0050(13) 0.0085(12) C12 0.0428(16) 0.0415(16) 0.0402(16) -0.0115(14) 0.0130(13) -0.0017(13) C13 0.0436(16) 0.065(2) 0.0286(16) -0.0133(14) -0.0011(13) 0.0023(14) C14 0.0343(14) 0.0562(18) 0.0309(15) -0.0067(14) -0.0028(12) 0.0099(13) B1 0.0381(16) 0.0253(15) 0.0317(16) -0.0005(13) 0.0073(13) -0.0021(13) N1 0.0341(11) 0.0239(11) 0.0269(12) -0.0007(9) 0.0076(9) 0.0008(9) N2 0.0396(12) 0.0235(11) 0.0262(12) -0.0003(9) 0.0083(9) -0.0046(9) Cl1 0.0503(5) 0.0495(5) 0.0496(5) 0.0000(3) 0.0010(3) -0.0191(3) Cl2 0.0513(4) 0.0335(4) 0.0366(4) 0.0072(3) 0.0083(3) 0.0084(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 C1 N2 1.330(3) . ? C1 N1 1.329(3) . ? C1 C2 1.479(3) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 N1 1.461(3) . ? C3 C8 1.518(3) . ? C3 C4 1.519(3) . ? C3 H3 0.9800 . ? C4 C5 1.523(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.526(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.510(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.519(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N2 1.455(3) . ? C9 C14 1.517(3) . ? C9 C10 1.517(3) . ? C9 H9 0.9800 . ? C10 C11 1.530(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.521(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.505(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.531(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? B1 N1 1.561(3) . ? B1 N2 1.571(3) . ? B1 Cl1 1.820(3) . ? B1 Cl2 1.846(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 N2 C1 N1 101.30(19) . . ? N2 C1 C2 129.3(2) . . ? N1 C1 C2 129.4(2) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 C8 109.16(19) . . ? N1 C3 C4 112.69(19) . . ? C8 C3 C4 110.82(19) . . ? N1 C3 H3 108.0 . . ? C8 C3 H3 108.0 . . ? C4 C3 H3 108.0 . . ? C3 C4 C5 110.9(2) . . ? C3 C4 H4A 109.5 . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C6 C5 C4 110.9(2) . . ? C6 C5 H5A 109.5 . . ? C4 C5 H5A 109.5 . . ? C6 C5 H5B 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 108.0 . . ? C7 C6 C5 110.9(2) . . ? C7 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.0 . . ? C6 C7 C8 111.5(2) . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C3 C8 C7 110.8(2) . . ? C3 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? N2 C9 C14 111.07(19) . . ? N2 C9 C10 110.82(19) . . ? C14 C9 C10 110.6(2) . . ? N2 C9 H9 108.1 . . ? C14 C9 H9 108.1 . . ? C10 C9 H9 108.1 . . ? C9 C10 C11 112.3(2) . . ? C9 C10 H10A 109.1 . . ? C11 C10 H10A 109.1 . . ? C9 C10 H10B 109.1 . . ? C11 C10 H10B 109.1 . . ? H10A C10 H10B 107.9 . . ? C12 C11 C10 111.7(2) . . ? C12 C11 H11A 109.3 . . ? C10 C11 H11A 109.3 . . ? C12 C11 H11B 109.3 . . ? C10 C11 H11B 109.3 . . ? H11A C11 H11B 107.9 . . ? C13 C12 C11 111.4(2) . . ? C13 C12 H12A 109.3 . . ? C11 C12 H12A 109.3 . . ? C13 C12 H12B 109.3 . . ? C11 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? C12 C13 C14 111.1(2) . . ? C12 C13 H13A 109.4 . . ? C14 C13 H13A 109.4 . . ? C12 C13 H13B 109.4 . . ? C14 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? C9 C14 C13 111.2(2) . . ? C9 C14 H14A 109.4 . . ? C13 C14 H14A 109.4 . . ? C9 C14 H14B 109.4 . . ? C13 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? N1 B1 N2 82.07(16) . . ? N1 B1 Cl1 115.95(18) . . ? N2 B1 Cl1 116.15(18) . . ? N1 B1 Cl2 114.48(18) . . ? N2 B1 Cl2 114.29(18) . . ? Cl1 B1 Cl2 111.21(15) . . ? C1 N1 C3 130.4(2) . . ? C1 N1 B1 88.54(18) . . ? C3 N1 B1 141.04(19) . . ? C1 N2 C9 130.6(2) . . ? C1 N2 B1 88.09(18) . . ? C9 N2 B1 141.16(19) . . ? 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 N1 C3 C4 C5 179.3(2) . . . . ? C8 C3 C4 C5 56.7(3) . . . . ? C3 C4 C5 C6 -56.1(3) . . . . ? C4 C5 C6 C7 55.6(3) . . . . ? C5 C6 C7 C8 -55.8(3) . . . . ? N1 C3 C8 C7 178.8(2) . . . . ? C4 C3 C8 C7 -56.5(3) . . . . ? C6 C7 C8 C3 56.3(3) . . . . ? N2 C9 C10 C11 177.72(19) . . . . ? C14 C9 C10 C11 54.1(3) . . . . ? C9 C10 C11 C12 -53.0(3) . . . . ? C10 C11 C12 C13 53.6(3) . . . . ? C11 C12 C13 C14 -55.7(3) . . . . ? N2 C9 C14 C13 -179.4(2) . . . . ? C10 C9 C14 C13 -55.9(3) . . . . ? C12 C13 C14 C9 57.3(3) . . . . ? N2 C1 N1 C3 -179.3(2) . . . . ? C2 C1 N1 C3 0.6(4) . . . . ? N2 C1 N1 B1 -0.3(2) . . . . ? C2 C1 N1 B1 179.7(2) . . . . ? C8 C3 N1 C1 -153.4(2) . . . . ? C4 C3 N1 C1 83.1(3) . . . . ? C8 C3 N1 B1 28.1(4) . . . . ? C4 C3 N1 B1 -95.5(3) . . . . ? N2 B1 N1 C1 0.21(17) . . . . ? Cl1 B1 N1 C1 -115.07(19) . . . . ? Cl2 B1 N1 C1 113.34(19) . . . . ? N2 B1 N1 C3 179.1(3) . . . . ? Cl1 B1 N1 C3 63.8(4) . . . . ? Cl2 B1 N1 C3 -67.8(4) . . . . ? N1 C1 N2 C9 176.5(2) . . . . ? C2 C1 N2 C9 -3.4(4) . . . . ? N1 C1 N2 B1 0.2(2) . . . . ? C2 C1 N2 B1 -179.7(2) . . . . ? C14 C9 N2 C1 -115.0(3) . . . . ? C10 C9 N2 C1 121.6(3) . . . . ? C14 C9 N2 B1 59.0(4) . . . . ? C10 C9 N2 B1 -64.4(3) . . . . ? N1 B1 N2 C1 -0.21(17) . . . . ? Cl1 B1 N2 C1 114.9(2) . . . . ? Cl2 B1 N2 C1 -113.55(19) . . . . ? N1 B1 N2 C9 -175.7(3) . . . . ? Cl1 B1 N2 C9 -60.6(3) . . . . ? Cl2 B1 N2 C9 71.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.256 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.060 data_mfnh019 _database_code_depnum_ccdc_archive 'CCDC 275322' _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; #3. data _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H23 B Br2 N2 Si2' _chemical_formula_sum 'C13 H23 B Br2 N2 Si2' _chemical_formula_weight 434.14 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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.329(5) _cell_length_b 10.887(5) _cell_length_c 13.019(5) _cell_angle_alpha 90 _cell_angle_beta 116.223(5) _cell_angle_gamma 90 _cell_volume 1949.1(13) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 4.275 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.4269 _exptl_absorpt_correction_T_max 0.4819 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3734 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2098 _reflns_number_gt 1755 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement Denzo _computing_data_reduction Scalepack _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0211P)^2^+3.4839P] 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 SHELXL _refine_ls_extinction_coef 0.0013(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2098 _refine_ls_number_parameters 94 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0694 _refine_ls_wR_factor_gt 0.0649 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 C1 C 0.5000 -0.0548(3) 0.2500 0.0210(7) Uani 1 2 d S . . C2 C 0.5000 -0.1901(3) 0.2500 0.0221(7) Uani 1 2 d S . . C3 C 0.4901(2) -0.2527(3) 0.3369(3) 0.0346(7) Uani 1 1 d . . . H3 H 0.4835 -0.2100 0.3949 0.042 Uiso 1 1 calc R . . C4 C 0.4904(2) -0.3808(3) 0.3360(3) 0.0461(8) Uani 1 1 d . . . H4 H 0.4841 -0.4239 0.3940 0.055 Uiso 1 1 calc R . . C5 C 0.5000 -0.4442(4) 0.2500 0.0411(11) Uani 1 2 d S . . H5 H 0.5000 -0.5296 0.2500 0.049 Uiso 1 2 calc SR . . C6 C 0.2539(2) -0.1406(3) 0.1209(3) 0.0413(8) Uani 1 1 d . . . H6A H 0.2880 -0.2095 0.1100 0.062 Uiso 1 1 calc R . . H6B H 0.1859 -0.1472 0.0697 0.062 Uiso 1 1 calc R . . H6C H 0.2625 -0.1396 0.1985 0.062 Uiso 1 1 calc R . . C7 C 0.2396(2) 0.1399(3) 0.1101(3) 0.0395(7) Uani 1 1 d . . . H7A H 0.2666 0.2128 0.0939 0.059 Uiso 1 1 calc R . . H7B H 0.2480 0.1429 0.1876 0.059 Uiso 1 1 calc R . . H7C H 0.1716 0.1350 0.0587 0.059 Uiso 1 1 calc R . . C8 C 0.2989(2) 0.0004(3) -0.0533(2) 0.0332(7) Uani 1 1 d . . . H8A H 0.3319 -0.0716 -0.0607 0.050 Uiso 1 1 calc R . . H8B H 0.3303 0.0724 -0.0636 0.050 Uiso 1 1 calc R . . H8C H 0.2324 -0.0012 -0.1105 0.050 Uiso 1 1 calc R . . B1 B 0.5000 0.1264(4) 0.2500 0.0208(8) Uani 1 2 d S . . N1 N 0.42512(14) 0.02113(19) 0.19337(17) 0.0221(5) Uani 1 1 d . . . Si1 Si 0.30275(5) 0.00336(7) 0.09097(6) 0.02464(18) Uani 1 1 d . . . Br1 Br 0.52467(2) 0.23070(3) 0.13894(2) 0.03064(13) 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 C1 0.0230(18) 0.0238(19) 0.0176(16) 0.000 0.0103(14) 0.000 C2 0.0216(17) 0.0213(18) 0.0208(17) 0.000 0.0072(15) 0.000 C3 0.0512(19) 0.0232(15) 0.0347(16) 0.0036(12) 0.0237(15) 0.0005(13) C4 0.062(2) 0.0296(18) 0.053(2) 0.0168(15) 0.0318(18) 0.0035(15) C5 0.043(2) 0.016(2) 0.060(3) 0.000 0.020(2) 0.000 C6 0.0342(16) 0.0446(19) 0.0398(17) -0.0003(14) 0.0115(13) -0.0145(14) C7 0.0331(16) 0.049(2) 0.0348(16) 0.0020(14) 0.0133(14) 0.0136(14) C8 0.0336(15) 0.0367(17) 0.0271(14) -0.0006(12) 0.0114(13) 0.0001(12) B1 0.025(2) 0.017(2) 0.022(2) 0.000 0.0131(17) 0.000 N1 0.0226(11) 0.0182(11) 0.0245(11) -0.0005(8) 0.0096(9) -0.0008(8) Si1 0.0210(4) 0.0275(4) 0.0237(4) 0.0002(3) 0.0083(3) -0.0011(3) Br1 0.03975(19) 0.02675(19) 0.03268(18) 0.00622(11) 0.02261(14) 0.00090(12) _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 C1 N1 1.340(3) 2_655 ? C1 N1 1.340(3) . ? C1 C2 1.474(5) . ? C2 C3 1.385(3) 2_655 ? C2 C3 1.385(3) . ? C3 C4 1.395(4) . ? C3 H3 0.9300 . ? C4 C5 1.377(4) . ? C4 H4 0.9300 . ? C5 C4 1.377(4) 2_655 ? C5 H5 0.9300 . ? C6 Si1 1.851(3) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 Si1 1.850(3) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 Si1 1.853(3) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? B1 N1 1.558(4) . ? B1 N1 1.558(4) 2_655 ? B1 Br1 2.002(2) 2_655 ? B1 Br1 2.002(2) . ? N1 Si1 1.767(2) . ? 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 C1 N1 103.9(3) 2_655 . ? N1 C1 C2 128.07(15) 2_655 . ? N1 C1 C2 128.07(15) . . ? C3 C2 C3 121.1(4) 2_655 . ? C3 C2 C1 119.45(18) 2_655 . ? C3 C2 C1 119.45(18) . . ? C2 C3 C4 118.9(3) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 120.7(3) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C4 119.9(4) 2_655 . ? C4 C5 H5 120.1 2_655 . ? C4 C5 H5 120.1 . . ? Si1 C6 H6A 109.5 . . ? Si1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? Si1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? Si1 C7 H7A 109.5 . . ? Si1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? Si1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? Si1 C8 H8A 109.5 . . ? Si1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? Si1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 B1 N1 85.3(3) . 2_655 ? N1 B1 Br1 115.11(8) . 2_655 ? N1 B1 Br1 114.23(8) 2_655 2_655 ? N1 B1 Br1 114.23(8) . . ? N1 B1 Br1 115.11(8) 2_655 . ? Br1 B1 Br1 110.88(19) 2_655 . ? C1 N1 B1 85.44(19) . . ? C1 N1 Si1 135.48(19) . . ? B1 N1 Si1 138.76(17) . . ? N1 Si1 C7 104.74(12) . . ? N1 Si1 C6 109.09(12) . . ? C7 Si1 C6 111.59(16) . . ? N1 Si1 C8 108.33(12) . . ? C7 Si1 C8 111.47(14) . . ? C6 Si1 C8 111.34(14) . . ? 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 N1 C1 C2 C3 -96.14(19) 2_655 . . 2_655 ? N1 C1 C2 C3 83.86(19) . . . 2_655 ? N1 C1 C2 C3 83.86(19) 2_655 . . . ? N1 C1 C2 C3 -96.14(19) . . . . ? C3 C2 C3 C4 0.1(2) 2_655 . . . ? C1 C2 C3 C4 -179.9(2) . . . . ? C2 C3 C4 C5 -0.2(5) . . . . ? C3 C4 C5 C4 0.1(2) . . . 2_655 ? N1 C1 N1 B1 0.0 2_655 . . . ? C2 C1 N1 B1 180.0 . . . . ? N1 C1 N1 Si1 174.2(3) 2_655 . . . ? C2 C1 N1 Si1 -5.8(3) . . . . ? N1 B1 N1 C1 0.0 2_655 . . . ? Br1 B1 N1 C1 -114.57(14) 2_655 . . . ? Br1 B1 N1 C1 115.44(14) . . . . ? N1 B1 N1 Si1 -173.8(3) 2_655 . . . ? Br1 B1 N1 Si1 71.6(2) 2_655 . . . ? Br1 B1 N1 Si1 -58.4(2) . . . . ? C1 N1 Si1 C7 154.5(2) . . . . ? B1 N1 Si1 C7 -34.3(2) . . . . ? C1 N1 Si1 C6 34.9(3) . . . . ? B1 N1 Si1 C6 -153.9(2) . . . . ? C1 N1 Si1 C8 -86.4(2) . . . . ? B1 N1 Si1 C8 84.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.519 _refine_diff_density_min -0.508 _refine_diff_density_rms 0.083 data_mfnh021 _database_code_depnum_ccdc_archive 'CCDC 275323' _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; _publ_section_references ; Allen, F.H. (2002). Acta Cryst. B58, 380-388. Cremer D. & Pople J.A. (1975). J. Am. Chem. Soc. 97, 1358-1367. Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. ; _publ_section_figure_captions ; ; _publ_section_exptl_prep ; ; #3. data _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H51 B Cl2 N2, 1.5(C6 H6)' _chemical_formula_sum 'C40 H60 B Cl2 N2' _chemical_formula_weight 650.61 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 monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.338(5) _cell_length_b 18.927(5) _cell_length_c 15.336(5) _cell_angle_alpha 90 _cell_angle_beta 92.677(5) _cell_angle_gamma 90 _cell_volume 3867(2) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.117 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1412 _exptl_absorpt_coefficient_mu 0.196 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9618 _exptl_absorpt_correction_T_max 0.9730 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa Nonius CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15927 _diffrn_reflns_av_R_equivalents 0.0821 _diffrn_reflns_av_sigmaI/netI 0.1409 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 27.00 _reflns_number_total 8407 _reflns_number_gt 3658 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement Denzo _computing_data_reduction Scalepack _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0681P)^2^+1.8394P] 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 8407 _refine_ls_number_parameters 406 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1775 _refine_ls_R_factor_gt 0.0604 _refine_ls_wR_factor_ref 0.1712 _refine_ls_wR_factor_gt 0.1287 _refine_ls_goodness_of_fit_ref 0.916 _refine_ls_restrained_S_all 0.916 _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 C1 C 0.4895(2) 0.17224(15) 0.77306(16) 0.0312(7) Uani 1 1 d . . . C2 C 0.3785(2) 0.17074(14) 0.76734(16) 0.0278(6) Uani 1 1 d . . . C3 C 0.3224(2) 0.14647(14) 0.83884(17) 0.0340(7) Uani 1 1 d . . . C4 C 0.2183(2) 0.14806(15) 0.82889(19) 0.0389(8) Uani 1 1 d . . . H4 H 0.1818 0.1303 0.8742 0.047 Uiso 1 1 calc R . . C5 C 0.1653(2) 0.17413(15) 0.75646(19) 0.0356(7) Uani 1 1 d . . . C6 C 0.2218(2) 0.19612(14) 0.68887(18) 0.0332(7) Uani 1 1 d . . . H6 H 0.1878 0.2130 0.6388 0.040 Uiso 1 1 calc R . . C7 C 0.3259(2) 0.19497(14) 0.68983(16) 0.0289(6) Uani 1 1 d . . . C8 C 0.3630(3) 0.11728(17) 0.92871(18) 0.0455(8) Uani 1 1 d . . . C9 C 0.4761(3) 0.11818(18) 0.94855(18) 0.0550(10) Uani 1 1 d . . . H9A H 0.5005 0.1657 0.9443 0.082 Uiso 1 1 calc R . . H9B H 0.5084 0.0888 0.9073 0.082 Uiso 1 1 calc R . . H9C H 0.4904 0.1006 1.0065 0.082 Uiso 1 1 calc R . . C10 C 0.3284(3) 0.04034(18) 0.9360(2) 0.0665(11) Uani 1 1 d . . . H10A H 0.2573 0.0376 0.9233 0.100 Uiso 1 1 calc R . . H10B H 0.3435 0.0234 0.9941 0.100 Uiso 1 1 calc R . . H10C H 0.3627 0.0118 0.8951 0.100 Uiso 1 1 calc R . . C11 C 0.3163(3) 0.16223(19) 1.00153(19) 0.0611(10) Uani 1 1 d . . . H11A H 0.3381 0.2104 0.9970 0.092 Uiso 1 1 calc R . . H11B H 0.3375 0.1438 1.0577 0.092 Uiso 1 1 calc R . . H11C H 0.2444 0.1603 0.9948 0.092 Uiso 1 1 calc R . . C12 C 0.0503(2) 0.17740(16) 0.7521(2) 0.0471(8) Uani 1 1 d . . . C13 C 0.0093(3) 0.10339(19) 0.7395(3) 0.0737(12) Uani 1 1 d . . . H13A H -0.0628 0.1049 0.7364 0.111 Uiso 1 1 calc R . . H13B H 0.0319 0.0744 0.7879 0.111 Uiso 1 1 calc R . . H13C H 0.0326 0.0839 0.6863 0.111 Uiso 1 1 calc R . . C14 C 0.0127(3) 0.2104(2) 0.8348(3) 0.0796(13) Uani 1 1 d . . . H14A H 0.0397 0.2572 0.8416 0.119 Uiso 1 1 calc R . . H14B H 0.0341 0.1822 0.8843 0.119 Uiso 1 1 calc R . . H14C H -0.0592 0.2127 0.8309 0.119 Uiso 1 1 calc R . . C15 C 0.0091(3) 0.2229(2) 0.6755(3) 0.0876(14) Uani 1 1 d . . . H15A H 0.0349 0.2700 0.6815 0.131 Uiso 1 1 calc R . . H15B H -0.0629 0.2241 0.6756 0.131 Uiso 1 1 calc R . . H15C H 0.0294 0.2030 0.6215 0.131 Uiso 1 1 calc R . . C16 C 0.3692(2) 0.22264(14) 0.60363(17) 0.0334(7) Uani 1 1 d . . . C17 C 0.4824(2) 0.22175(16) 0.59488(18) 0.0414(8) Uani 1 1 d . . . H17A H 0.4981 0.2406 0.5390 0.062 Uiso 1 1 calc R . . H17B H 0.5065 0.1741 0.5999 0.062 Uiso 1 1 calc R . . H17C H 0.5140 0.2501 0.6403 0.062 Uiso 1 1 calc R . . C18 C 0.3354(2) 0.29996(15) 0.59058(19) 0.0461(8) Uani 1 1 d . . . H18A H 0.3614 0.3180 0.5377 0.069 Uiso 1 1 calc R . . H18B H 0.3605 0.3279 0.6391 0.069 Uiso 1 1 calc R . . H18C H 0.2635 0.3021 0.5868 0.069 Uiso 1 1 calc R . . C19 C 0.3245(2) 0.17775(16) 0.52688(18) 0.0459(8) Uani 1 1 d . . . H19A H 0.3500 0.1945 0.4731 0.069 Uiso 1 1 calc R . . H19B H 0.2527 0.1818 0.5245 0.069 Uiso 1 1 calc R . . H19C H 0.3432 0.1292 0.5354 0.069 Uiso 1 1 calc R . . C20 C 0.5407(2) 0.04582(15) 0.74226(17) 0.0365(7) Uani 1 1 d . . . H20 H 0.4786 0.0307 0.7685 0.044 Uiso 1 1 calc R . . C21 C 0.5323(2) 0.02968(15) 0.64473(17) 0.0402(8) Uani 1 1 d . . . H21A H 0.4740 0.0537 0.6187 0.048 Uiso 1 1 calc R . . H21B H 0.5912 0.0477 0.6174 0.048 Uiso 1 1 calc R . . C22 C 0.5230(2) -0.04919(16) 0.6271(2) 0.0477(8) Uani 1 1 d . . . H22A H 0.4603 -0.0662 0.6488 0.057 Uiso 1 1 calc R . . H22B H 0.5216 -0.0574 0.5647 0.057 Uiso 1 1 calc R . . C23 C 0.6092(3) -0.09002(16) 0.67025(19) 0.0477(8) Uani 1 1 d . . . H23A H 0.6711 -0.0774 0.6434 0.057 Uiso 1 1 calc R . . H23B H 0.5981 -0.1402 0.6615 0.057 Uiso 1 1 calc R . . C24 C 0.6187(3) -0.07422(17) 0.7674(2) 0.0579(10) Uani 1 1 d . . . H24A H 0.5600 -0.0921 0.7952 0.069 Uiso 1 1 calc R . . H24B H 0.6772 -0.0984 0.7928 0.069 Uiso 1 1 calc R . . C25 C 0.6287(3) 0.00423(16) 0.78476(19) 0.0494(9) Uani 1 1 d . . . H25A H 0.6910 0.0211 0.7621 0.059 Uiso 1 1 calc R . . H25B H 0.6314 0.0124 0.8473 0.059 Uiso 1 1 calc R . . C26 C 0.5296(2) 0.30013(15) 0.81120(18) 0.0388(8) Uani 1 1 d . . . H26 H 0.4647 0.3125 0.7826 0.047 Uiso 1 1 calc R . . C27 C 0.5233(3) 0.31282(16) 0.90865(19) 0.0493(9) Uani 1 1 d . . . H27A H 0.5846 0.2962 0.9385 0.059 Uiso 1 1 calc R . . H27B H 0.4678 0.2858 0.9302 0.059 Uiso 1 1 calc R . . C28 C 0.5085(3) 0.39091(17) 0.9295(2) 0.0572(10) Uani 1 1 d . . . H28A H 0.4431 0.4060 0.9061 0.069 Uiso 1 1 calc R . . H28B H 0.5099 0.3972 0.9923 0.069 Uiso 1 1 calc R . . C29 C 0.5886(3) 0.43649(17) 0.8918(2) 0.0533(9) Uani 1 1 d . . . H29A H 0.6533 0.4252 0.9198 0.064 Uiso 1 1 calc R . . H29B H 0.5744 0.4858 0.9030 0.064 Uiso 1 1 calc R . . C30 C 0.5923(3) 0.42450(16) 0.7943(2) 0.0572(10) Uani 1 1 d . . . H30A H 0.6460 0.4526 0.7715 0.069 Uiso 1 1 calc R . . H30B H 0.5296 0.4398 0.7658 0.069 Uiso 1 1 calc R . . C31 C 0.6098(3) 0.34702(16) 0.7741(2) 0.0506(9) Uani 1 1 d . . . H31A H 0.6751 0.3329 0.7986 0.061 Uiso 1 1 calc R . . H31B H 0.6097 0.3406 0.7114 0.061 Uiso 1 1 calc R . . C39 C 0.5109(4) 0.4360(2) 0.5328(4) 0.124(2) Uani 1 1 d . . . H39 H 0.5170 0.3899 0.5535 0.149 Uiso 1 1 calc R . . C40 C 0.5812(3) 0.4828(2) 0.5537(2) 0.0588(10) Uani 1 1 d . . . H40 H 0.6354 0.4716 0.5915 0.071 Uiso 1 1 calc R . . C38 C 0.4286(4) 0.4547(3) 0.4806(4) 0.135(2) Uani 1 1 d . . . H38 H 0.3783 0.4215 0.4694 0.162 Uiso 1 1 calc R . . C36 C 0.2492(4) 0.4812(4) 0.9191(6) 0.111(2) Uani 1 1 d . . . H36 H 0.2537 0.5228 0.9512 0.134 Uiso 1 1 calc R . . C37 C 0.2543(3) 0.4835(3) 0.8342(5) 0.0907(17) Uani 1 1 d . . . H37 H 0.2607 0.5265 0.8057 0.109 Uiso 1 1 calc R . . C32 C 0.2503(3) 0.4226(4) 0.7887(3) 0.0899(16) Uani 1 1 d . . . H32 H 0.2559 0.4233 0.7285 0.108 Uiso 1 1 calc R . . C33 C 0.2382(4) 0.3617(3) 0.8297(6) 0.100(2) Uani 1 1 d . . . H33 H 0.2340 0.3199 0.7979 0.121 Uiso 1 1 calc R . . C34 C 0.2320(4) 0.3600(4) 0.9146(7) 0.118(3) Uani 1 1 d . . . H34 H 0.2239 0.3171 0.9428 0.141 Uiso 1 1 calc R . . C35 C 0.2374(4) 0.4194(6) 0.9607(3) 0.123(3) Uani 1 1 d . . . H35 H 0.2330 0.4183 1.0210 0.147 Uiso 1 1 calc R . . B1 B 0.6419(3) 0.1753(2) 0.7801(2) 0.0443(10) Uani 1 1 d . . . N1 N 0.55585(17) 0.12071(12) 0.76019(13) 0.0334(6) Uani 1 1 d . . . N2 N 0.55108(17) 0.22619(13) 0.79152(14) 0.0357(6) Uani 1 1 d . . . Cl1 Cl 0.71888(7) 0.16132(5) 0.88073(5) 0.0620(3) Uani 1 1 d . . . Cl2 Cl 0.72138(6) 0.19282(5) 0.68831(6) 0.0578(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 C1 0.0305(17) 0.0445(19) 0.0181(14) 0.0012(12) -0.0046(12) 0.0026(16) C2 0.0241(16) 0.0316(16) 0.0276(15) -0.0025(12) -0.0001(12) 0.0014(13) C3 0.0341(19) 0.0350(17) 0.0332(16) 0.0023(13) 0.0046(13) 0.0058(14) C4 0.038(2) 0.0362(18) 0.0441(18) 0.0014(14) 0.0163(15) -0.0027(15) C5 0.0279(18) 0.0321(17) 0.0470(18) -0.0082(14) 0.0055(15) -0.0019(14) C6 0.0273(17) 0.0355(17) 0.0361(16) -0.0048(13) -0.0054(13) 0.0011(14) C7 0.0263(17) 0.0291(16) 0.0310(15) -0.0027(12) -0.0027(12) -0.0015(13) C8 0.052(2) 0.053(2) 0.0323(17) 0.0103(15) 0.0083(15) 0.0096(17) C9 0.069(3) 0.069(2) 0.0266(16) 0.0090(15) -0.0025(16) 0.021(2) C10 0.086(3) 0.059(2) 0.056(2) 0.0257(18) 0.017(2) 0.013(2) C11 0.072(3) 0.077(3) 0.0351(18) 0.0044(17) 0.0108(17) 0.018(2) C12 0.0250(18) 0.048(2) 0.069(2) -0.0102(17) 0.0099(16) -0.0037(16) C13 0.037(2) 0.065(3) 0.119(3) -0.027(2) 0.006(2) -0.012(2) C14 0.037(2) 0.096(3) 0.108(3) -0.037(3) 0.019(2) 0.000(2) C15 0.025(2) 0.108(4) 0.129(4) 0.019(3) 0.002(2) 0.012(2) C16 0.0310(18) 0.0397(18) 0.0287(15) 0.0018(13) -0.0048(13) -0.0006(14) C17 0.038(2) 0.055(2) 0.0310(16) 0.0060(14) 0.0020(14) -0.0038(16) C18 0.052(2) 0.046(2) 0.0406(18) 0.0102(15) -0.0014(15) 0.0018(17) C19 0.044(2) 0.060(2) 0.0337(17) -0.0030(15) -0.0040(15) -0.0018(17) C20 0.0334(18) 0.0408(19) 0.0355(17) -0.0037(13) 0.0017(13) 0.0002(15) C21 0.0390(19) 0.046(2) 0.0342(16) -0.0020(14) -0.0070(14) 0.0049(16) C22 0.046(2) 0.047(2) 0.0495(19) -0.0118(15) -0.0036(16) 0.0036(17) C23 0.051(2) 0.045(2) 0.0472(19) -0.0024(15) 0.0052(16) 0.0078(17) C24 0.074(3) 0.054(2) 0.046(2) 0.0087(16) 0.0020(18) 0.0195(19) C25 0.062(2) 0.052(2) 0.0331(17) -0.0022(15) -0.0099(16) 0.0183(18) C26 0.0284(17) 0.0442(19) 0.0427(18) -0.0089(14) -0.0097(14) 0.0041(15) C27 0.055(2) 0.049(2) 0.0432(19) -0.0090(15) -0.0006(16) 0.0010(17) C28 0.063(3) 0.057(2) 0.052(2) -0.0166(17) -0.0027(18) 0.007(2) C29 0.050(2) 0.045(2) 0.064(2) -0.0144(17) -0.0161(18) 0.0036(18) C30 0.064(3) 0.041(2) 0.065(2) -0.0039(17) -0.0049(19) -0.0053(18) C31 0.051(2) 0.051(2) 0.050(2) -0.0063(16) -0.0003(16) -0.0054(18) C39 0.101(4) 0.074(3) 0.190(5) 0.063(3) -0.061(4) -0.043(3) C40 0.049(2) 0.069(3) 0.058(2) 0.0092(19) -0.0019(18) -0.009(2) C38 0.113(5) 0.072(3) 0.210(6) 0.061(4) -0.089(4) -0.058(3) C36 0.067(3) 0.101(5) 0.159(6) -0.089(4) -0.065(4) 0.046(3) C37 0.050(3) 0.059(3) 0.161(5) 0.048(3) -0.027(3) -0.015(2) C32 0.051(3) 0.169(6) 0.050(2) -0.011(3) 0.005(2) 0.008(4) C33 0.048(3) 0.060(4) 0.193(7) -0.066(4) -0.008(4) 0.001(3) C34 0.047(3) 0.099(5) 0.209(8) 0.095(5) 0.030(5) 0.017(3) C35 0.059(3) 0.260(9) 0.049(3) 0.012(5) 0.003(2) 0.077(6) B1 0.029(2) 0.056(2) 0.047(2) -0.0099(18) -0.0117(17) 0.0029(18) N1 0.0260(14) 0.0428(16) 0.0310(13) -0.0036(11) -0.0038(10) 0.0090(12) N2 0.0257(14) 0.0421(16) 0.0384(14) -0.0064(11) -0.0063(11) 0.0005(12) Cl1 0.0427(5) 0.0815(7) 0.0592(5) -0.0164(5) -0.0261(4) 0.0142(5) Cl2 0.0300(5) 0.0770(6) 0.0668(6) -0.0095(5) 0.0058(4) -0.0029(4) _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 C1 N2 1.333(3) . ? C1 N1 1.338(3) . ? C1 C2 1.479(4) . ? C2 C7 1.427(4) . ? C2 C3 1.431(4) . ? C3 C4 1.390(4) . ? C3 C8 1.558(4) . ? C4 C5 1.380(4) . ? C4 H4 0.9300 . ? C5 C6 1.374(4) . ? C5 C12 1.533(4) . ? C6 C7 1.389(4) . ? C6 H6 0.9300 . ? C7 C16 1.558(4) . ? C8 C9 1.525(5) . ? C8 C10 1.533(4) . ? C8 C11 1.557(4) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.513(4) . ? C12 C14 1.521(5) . ? C12 C15 1.537(5) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.523(4) . ? C16 C18 1.541(4) . ? C16 C19 1.548(4) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 N1 1.456(4) . ? C20 C21 1.526(4) . ? C20 C25 1.534(4) . ? C20 H20 0.9800 . ? C21 C22 1.521(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.511(4) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.519(4) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.513(4) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 N2 1.463(4) . ? C26 C27 1.520(4) . ? C26 C31 1.521(4) . ? C26 H26 0.9800 . ? C27 C28 1.527(4) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.510(5) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.515(4) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.519(4) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C39 C40 1.319(5) . ? C39 C38 1.374(6) . ? C39 H39 0.9300 . ? C40 C38 1.299(5) 3_666 ? C40 H40 0.9300 . ? C38 C40 1.299(5) 3_666 ? C38 H38 0.9300 . ? C36 C37 1.308(8) . ? C36 C35 1.344(8) . ? C36 H36 0.9300 . ? C37 C32 1.347(7) . ? C37 H37 0.9300 . ? C32 C33 1.327(7) . ? C32 H32 0.9300 . ? C33 C34 1.308(8) . ? C33 H33 0.9300 . ? C34 C35 1.328(8) . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? B1 N2 1.564(4) . ? B1 N1 1.565(4) . ? B1 Cl2 1.832(4) . ? B1 Cl1 1.832(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 100.6(2) . . ? N2 C1 C2 129.3(3) . . ? N1 C1 C2 130.1(3) . . ? C7 C2 C3 119.2(3) . . ? C7 C2 C1 119.6(2) . . ? C3 C2 C1 121.2(2) . . ? C4 C3 C2 117.6(2) . . ? C4 C3 C8 114.1(3) . . ? C2 C3 C8 128.2(3) . . ? C5 C4 C3 124.6(3) . . ? C5 C4 H4 117.7 . . ? C3 C4 H4 117.7 . . ? C6 C5 C4 115.9(3) . . ? C6 C5 C12 122.5(3) . . ? C4 C5 C12 121.6(3) . . ? C5 C6 C7 124.8(3) . . ? C5 C6 H6 117.6 . . ? C7 C6 H6 117.6 . . ? C6 C7 C2 117.8(2) . . ? C6 C7 C16 113.3(2) . . ? C2 C7 C16 128.9(2) . . ? C9 C8 C10 107.1(3) . . ? C9 C8 C11 106.0(3) . . ? C10 C8 C11 109.6(3) . . ? C9 C8 C3 118.2(2) . . ? C10 C8 C3 107.9(3) . . ? C11 C8 C3 107.8(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C14 110.8(3) . . ? C13 C12 C5 108.9(3) . . ? C14 C12 C5 110.3(3) . . ? C13 C12 C15 107.9(3) . . ? C14 C12 C15 106.7(3) . . ? C5 C12 C15 112.2(3) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C18 106.5(2) . . ? C17 C16 C19 106.0(2) . . ? C18 C16 C19 108.8(2) . . ? C17 C16 C7 118.6(2) . . ? C18 C16 C7 108.2(2) . . ? C19 C16 C7 108.4(2) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N1 C20 C21 112.5(2) . . ? N1 C20 C25 108.8(2) . . ? C21 C20 C25 109.5(2) . . ? N1 C20 H20 108.7 . . ? C21 C20 H20 108.7 . . ? C25 C20 H20 108.7 . . ? C22 C21 C20 111.8(2) . . ? C22 C21 H21A 109.2 . . ? C20 C21 H21A 109.2 . . ? C22 C21 H21B 109.2 . . ? C20 C21 H21B 109.2 . . ? H21A C21 H21B 107.9 . . ? C23 C22 C21 111.8(3) . . ? C23 C22 H22A 109.3 . . ? C21 C22 H22A 109.3 . . ? C23 C22 H22B 109.3 . . ? C21 C22 H22B 109.3 . . ? H22A C22 H22B 107.9 . . ? C22 C23 C24 110.8(3) . . ? C22 C23 H23A 109.5 . . ? C24 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? C24 C23 H23B 109.5 . . ? H23A C23 H23B 108.1 . . ? C25 C24 C23 111.6(2) . . ? C25 C24 H24A 109.3 . . ? C23 C24 H24A 109.3 . . ? C25 C24 H24B 109.3 . . ? C23 C24 H24B 109.3 . . ? H24A C24 H24B 108.0 . . ? C24 C25 C20 111.7(3) . . ? C24 C25 H25A 109.3 . . ? C20 C25 H25A 109.3 . . ? C24 C25 H25B 109.3 . . ? C20 C25 H25B 109.3 . . ? H25A C25 H25B 107.9 . . ? N2 C26 C27 112.0(2) . . ? N2 C26 C31 109.4(2) . . ? C27 C26 C31 110.3(2) . . ? N2 C26 H26 108.3 . . ? C27 C26 H26 108.3 . . ? C31 C26 H26 108.3 . . ? C26 C27 C28 111.9(3) . . ? C26 C27 H27A 109.2 . . ? C28 C27 H27A 109.2 . . ? C26 C27 H27B 109.2 . . ? C28 C27 H27B 109.2 . . ? H27A C27 H27B 107.9 . . ? C29 C28 C27 111.8(3) . . ? C29 C28 H28A 109.3 . . ? C27 C28 H28A 109.3 . . ? C29 C28 H28B 109.3 . . ? C27 C28 H28B 109.3 . . ? H28A C28 H28B 107.9 . . ? C28 C29 C30 110.4(3) . . ? C28 C29 H29A 109.6 . . ? C30 C29 H29A 109.6 . . ? C28 C29 H29B 109.6 . . ? C30 C29 H29B 109.6 . . ? H29A C29 H29B 108.1 . . ? C29 C30 C31 111.0(3) . . ? C29 C30 H30A 109.4 . . ? C31 C30 H30A 109.4 . . ? C29 C30 H30B 109.4 . . ? C31 C30 H30B 109.4 . . ? H30A C30 H30B 108.0 . . ? C30 C31 C26 111.7(3) . . ? C30 C31 H31A 109.3 . . ? C26 C31 H31A 109.3 . . ? C30 C31 H31B 109.3 . . ? C26 C31 H31B 109.3 . . ? H31A C31 H31B 107.9 . . ? C40 C39 C38 120.5(4) . . ? C40 C39 H39 119.7 . . ? C38 C39 H39 119.7 . . ? C38 C40 C39 117.1(4) 3_666 . ? C38 C40 H40 121.4 3_666 . ? C39 C40 H40 121.4 . . ? C40 C38 C39 122.3(4) 3_666 . ? C40 C38 H38 118.9 3_666 . ? C39 C38 H38 118.9 . . ? C37 C36 C35 121.0(5) . . ? C37 C36 H36 119.5 . . ? C35 C36 H36 119.5 . . ? C36 C37 C32 119.0(4) . . ? C36 C37 H37 120.5 . . ? C32 C37 H37 120.5 . . ? C33 C32 C37 120.0(4) . . ? C33 C32 H32 120.0 . . ? C37 C32 H32 120.0 . . ? C34 C33 C32 120.5(5) . . ? C34 C33 H33 119.7 . . ? C32 C33 H33 119.7 . . ? C33 C34 C35 120.3(5) . . ? C33 C34 H34 119.8 . . ? C35 C34 H34 119.8 . . ? C34 C35 C36 119.2(5) . . ? C34 C35 H35 120.4 . . ? C36 C35 H35 120.4 . . ? N2 B1 N1 82.1(2) . . ? N2 B1 Cl2 117.0(2) . . ? N1 B1 Cl2 114.5(2) . . ? N2 B1 Cl1 113.7(2) . . ? N1 B1 Cl1 116.5(2) . . ? Cl2 B1 Cl1 110.62(19) . . ? C1 N1 C20 130.6(2) . . ? C1 N1 B1 88.5(2) . . ? C20 N1 B1 140.8(2) . . ? C1 N2 C26 130.7(2) . . ? C1 N2 B1 88.8(2) . . ? C26 N2 B1 140.6(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 C1 C2 C7 80.8(3) . . . . ? N1 C1 C2 C7 -98.2(3) . . . . ? N2 C1 C2 C3 -98.2(3) . . . . ? N1 C1 C2 C3 82.8(4) . . . . ? C7 C2 C3 C4 -0.2(4) . . . . ? C1 C2 C3 C4 178.7(3) . . . . ? C7 C2 C3 C8 179.4(3) . . . . ? C1 C2 C3 C8 -1.6(4) . . . . ? C2 C3 C4 C5 -2.9(4) . . . . ? C8 C3 C4 C5 177.5(3) . . . . ? C3 C4 C5 C6 3.6(4) . . . . ? C3 C4 C5 C12 -177.0(3) . . . . ? C4 C5 C6 C7 -1.3(4) . . . . ? C12 C5 C6 C7 179.3(3) . . . . ? C5 C6 C7 C2 -1.5(4) . . . . ? C5 C6 C7 C16 179.6(2) . . . . ? C3 C2 C7 C6 2.3(4) . . . . ? C1 C2 C7 C6 -176.7(2) . . . . ? C3 C2 C7 C16 -179.1(2) . . . . ? C1 C2 C7 C16 2.0(4) . . . . ? C4 C3 C8 C9 -175.8(3) . . . . ? C2 C3 C8 C9 4.6(4) . . . . ? C4 C3 C8 C10 62.6(3) . . . . ? C2 C3 C8 C10 -117.0(3) . . . . ? C4 C3 C8 C11 -55.7(3) . . . . ? C2 C3 C8 C11 124.7(3) . . . . ? C6 C5 C12 C13 105.9(3) . . . . ? C4 C5 C12 C13 -73.5(4) . . . . ? C6 C5 C12 C14 -132.3(3) . . . . ? C4 C5 C12 C14 48.4(4) . . . . ? C6 C5 C12 C15 -13.4(4) . . . . ? C4 C5 C12 C15 167.2(3) . . . . ? C6 C7 C16 C17 -177.9(2) . . . . ? C2 C7 C16 C17 3.4(4) . . . . ? C6 C7 C16 C18 60.8(3) . . . . ? C2 C7 C16 C18 -117.9(3) . . . . ? C6 C7 C16 C19 -57.1(3) . . . . ? C2 C7 C16 C19 124.2(3) . . . . ? N1 C20 C21 C22 176.4(2) . . . . ? C25 C20 C21 C22 55.3(3) . . . . ? C20 C21 C22 C23 -55.9(4) . . . . ? C21 C22 C23 C24 54.7(4) . . . . ? C22 C23 C24 C25 -55.1(4) . . . . ? C23 C24 C25 C20 56.3(4) . . . . ? N1 C20 C25 C24 -179.0(2) . . . . ? C21 C20 C25 C24 -55.7(3) . . . . ? N2 C26 C27 C28 175.8(3) . . . . ? C31 C26 C27 C28 53.7(4) . . . . ? C26 C27 C28 C29 -54.7(4) . . . . ? C27 C28 C29 C30 55.6(4) . . . . ? C28 C29 C30 C31 -56.7(4) . . . . ? C29 C30 C31 C26 57.2(4) . . . . ? N2 C26 C31 C30 -178.8(2) . . . . ? C27 C26 C31 C30 -55.2(3) . . . . ? C38 C39 C40 C38 -3.4(10) . . . 3_666 ? C40 C39 C38 C40 3.6(11) . . . 3_666 ? C35 C36 C37 C32 -1.7(7) . . . . ? C36 C37 C32 C33 2.0(7) . . . . ? C37 C32 C33 C34 -1.3(8) . . . . ? C32 C33 C34 C35 0.3(8) . . . . ? C33 C34 C35 C36 0.0(8) . . . . ? C37 C36 C35 C34 0.7(8) . . . . ? N2 C1 N1 C20 176.1(2) . . . . ? C2 C1 N1 C20 -4.7(4) . . . . ? N2 C1 N1 B1 0.2(2) . . . . ? C2 C1 N1 B1 179.4(3) . . . . ? C21 C20 N1 C1 91.9(3) . . . . ? C25 C20 N1 C1 -146.6(3) . . . . ? C21 C20 N1 B1 -94.6(4) . . . . ? C25 C20 N1 B1 26.9(4) . . . . ? N2 B1 N1 C1 -0.16(19) . . . . ? Cl2 B1 N1 C1 -116.3(2) . . . . ? Cl1 B1 N1 C1 112.4(2) . . . . ? N2 B1 N1 C20 -175.3(3) . . . . ? Cl2 B1 N1 C20 68.6(4) . . . . ? Cl1 B1 N1 C20 -62.7(4) . . . . ? N1 C1 N2 C26 178.8(2) . . . . ? C2 C1 N2 C26 -0.4(4) . . . . ? N1 C1 N2 B1 -0.2(2) . . . . ? C2 C1 N2 B1 -179.4(3) . . . . ? C27 C26 N2 C1 92.0(3) . . . . ? C31 C26 N2 C1 -145.3(3) . . . . ? C27 C26 N2 B1 -89.6(4) . . . . ? C31 C26 N2 B1 33.0(4) . . . . ? N1 B1 N2 C1 0.16(19) . . . . ? Cl2 B1 N2 C1 113.7(2) . . . . ? Cl1 B1 N2 C1 -115.4(2) . . . . ? N1 B1 N2 C26 -178.6(3) . . . . ? Cl2 B1 N2 C26 -65.1(4) . . . . ? Cl1 B1 N2 C26 65.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.266 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.048 data_nhnh022 _database_code_depnum_ccdc_archive 'CCDC 275324' _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; _publ_section_references ; Allen, F.H. (2002). Acta Cryst. B58, 380-388. Cremer D. & Pople J.A. (1975). J. Am. Chem. Soc. 97, 1358-1367. Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. ; #3. data _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H23 B Cl2 N2 Si2' _chemical_formula_sum 'C13 H23 B Cl2 N2 Si2' _chemical_formula_weight 345.22 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' Si Si 0.0817 0.0704 '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 monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.026(5) _cell_length_b 10.799(5) _cell_length_c 12.711(5) _cell_angle_alpha 90 _cell_angle_beta 114.477(5) _cell_angle_gamma 90 _cell_volume 1877.2(13) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.466 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9126 _exptl_absorpt_correction_T_max 0.9126 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3390 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_sigmaI/netI 0.1340 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2140 _reflns_number_gt 1006 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement Denzo _computing_data_reduction Scalepack _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0743P)^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_number_reflns 2140 _refine_ls_number_parameters 93 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1621 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1546 _refine_ls_wR_factor_gt 0.1181 _refine_ls_goodness_of_fit_ref 0.929 _refine_ls_restrained_S_all 0.929 _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 C1 C 0.0000 0.4463(5) 0.2500 0.0318(12) Uani 1 2 d S . . C2 C 0.0000 0.3090(4) 0.2500 0.0317(12) Uani 1 2 d S . . C3 C 0.0025(3) 0.2464(3) 0.1562(3) 0.0432(10) Uani 1 1 d . . . H3 H 0.0043 0.2891 0.0936 0.052 Uiso 1 1 calc R . . C4 C 0.0024(3) 0.1184(4) 0.1586(3) 0.0554(12) Uani 1 1 d . . . H4 H 0.0040 0.0750 0.0962 0.066 Uiso 1 1 calc R . . C5 C 0.0000 0.0534(6) 0.2500 0.0568(17) Uani 1 2 d S . . H5 H 0.0000 -0.0327 0.2500 0.068 Uiso 1 2 calc SR . . C6 C -0.2470(3) 0.3595(4) 0.1235(3) 0.0462(10) Uani 1 1 d . . . H6A H -0.2121 0.2897 0.1127 0.069 Uiso 1 1 calc R . . H6B H -0.3150 0.3525 0.0725 0.069 Uiso 1 1 calc R . . H6C H -0.2399 0.3613 0.2021 0.069 Uiso 1 1 calc R . . C7 C -0.1982(3) 0.4994(4) -0.0555(3) 0.0456(10) Uani 1 1 d . . . H7A H -0.1643 0.4268 -0.0629 0.068 Uiso 1 1 calc R . . H7B H -0.1662 0.5719 -0.0668 0.068 Uiso 1 1 calc R . . H7C H -0.2645 0.4973 -0.1125 0.068 Uiso 1 1 calc R . . C8 C -0.2615(3) 0.6413(4) 0.1110(3) 0.0436(10) Uani 1 1 d . . . H8A H -0.2341 0.7146 0.0937 0.065 Uiso 1 1 calc R . . H8B H -0.2544 0.6447 0.1896 0.065 Uiso 1 1 calc R . . H8C H -0.3297 0.6360 0.0600 0.065 Uiso 1 1 calc R . . B1 B 0.0000 0.6310(5) 0.2500 0.0329(14) Uani 1 2 d S . . N1 N -0.0746(2) 0.5218(2) 0.1932(2) 0.0302(7) Uani 1 1 d . . . Si1 Si -0.19703(7) 0.50358(9) 0.09136(8) 0.0343(3) Uani 1 1 d . . . Cl1 Cl -0.02490(7) 0.72621(9) 0.35369(8) 0.0434(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 C1 0.035(3) 0.032(3) 0.028(3) 0.000 0.013(3) 0.000 C2 0.027(3) 0.033(3) 0.029(3) 0.000 0.006(2) 0.000 C3 0.057(3) 0.035(2) 0.035(2) -0.0059(18) 0.017(2) 0.0109(19) C4 0.065(3) 0.043(3) 0.056(3) -0.017(2) 0.022(2) -0.005(2) C5 0.045(4) 0.035(3) 0.074(5) 0.000 0.008(3) 0.000 C6 0.042(2) 0.050(3) 0.043(2) -0.0028(19) 0.0141(19) -0.012(2) C7 0.045(2) 0.054(3) 0.036(2) -0.0020(19) 0.0155(19) 0.000(2) C8 0.037(2) 0.053(3) 0.035(2) 0.0020(18) 0.0096(19) 0.0093(19) B1 0.033(4) 0.029(3) 0.030(3) 0.000 0.006(3) 0.000 N1 0.0294(17) 0.0270(16) 0.0297(16) -0.0013(13) 0.0076(14) 0.0030(13) Si1 0.0309(6) 0.0369(6) 0.0298(6) 0.0010(5) 0.0072(5) -0.0006(5) Cl1 0.0543(7) 0.0384(6) 0.0419(6) -0.0071(4) 0.0243(5) 0.0001(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 C1 N1 1.331(4) 2 ? C1 N1 1.331(4) . ? C1 C2 1.483(7) . ? C2 C3 1.385(4) . ? C2 C3 1.385(4) 2 ? C3 C4 1.383(5) . ? C3 H3 0.9300 . ? C4 C5 1.370(5) . ? C4 H4 0.9300 . ? C5 C4 1.370(5) 2 ? C5 H5 0.9300 . ? C6 Si1 1.846(4) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 Si1 1.860(4) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 Si1 1.848(4) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? B1 N1 1.580(5) . ? B1 N1 1.580(5) 2 ? B1 Cl1 1.828(3) 2 ? B1 Cl1 1.828(3) . ? N1 Si1 1.768(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 N1 C1 N1 104.4(4) 2 . ? N1 C1 C2 127.8(2) 2 . ? N1 C1 C2 127.8(2) . . ? C3 C2 C3 121.5(5) . 2 ? C3 C2 C1 119.2(2) . . ? C3 C2 C1 119.2(2) 2 . ? C4 C3 C2 118.0(4) . . ? C4 C3 H3 121.0 . . ? C2 C3 H3 121.0 . . ? C5 C4 C3 122.1(4) . . ? C5 C4 H4 119.0 . . ? C3 C4 H4 119.0 . . ? C4 C5 C4 118.4(6) . 2 ? C4 C5 H5 120.8 . . ? C4 C5 H5 120.8 2 . ? Si1 C6 H6A 109.5 . . ? Si1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? Si1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? Si1 C7 H7A 109.5 . . ? Si1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? Si1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? Si1 C8 H8A 109.5 . . ? Si1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? Si1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 B1 N1 83.5(3) . 2 ? N1 B1 Cl1 114.11(11) . 2 ? N1 B1 Cl1 115.52(11) 2 2 ? N1 B1 Cl1 115.52(11) . . ? N1 B1 Cl1 114.11(11) 2 . ? Cl1 B1 Cl1 111.6(3) 2 . ? C1 N1 B1 86.1(3) . . ? C1 N1 Si1 135.7(3) . . ? B1 N1 Si1 138.0(2) . . ? N1 Si1 C6 109.10(16) . . ? N1 Si1 C8 104.86(15) . . ? C6 Si1 C8 111.34(17) . . ? N1 Si1 C7 108.15(15) . . ? C6 Si1 C7 111.50(17) . . ? C8 Si1 C7 111.60(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 N1 C1 C2 C3 -102.5(2) 2 . . . ? N1 C1 C2 C3 77.5(2) . . . . ? N1 C1 C2 C3 77.5(2) 2 . . 2 ? N1 C1 C2 C3 -102.5(2) . . . 2 ? C3 C2 C3 C4 0.0(3) 2 . . . ? C1 C2 C3 C4 -180.0(3) . . . . ? C2 C3 C4 C5 -0.1(5) . . . . ? C3 C4 C5 C4 0.0(3) . . . 2 ? N1 C1 N1 B1 0.0 2 . . . ? C2 C1 N1 B1 180.0 . . . . ? N1 C1 N1 Si1 175.1(3) 2 . . . ? C2 C1 N1 Si1 -4.9(3) . . . . ? N1 B1 N1 C1 0.0 2 . . . ? Cl1 B1 N1 C1 115.1(2) 2 . . . ? Cl1 B1 N1 C1 -113.6(2) . . . . ? N1 B1 N1 Si1 -174.9(3) 2 . . . ? Cl1 B1 N1 Si1 -59.8(3) 2 . . . ? Cl1 B1 N1 Si1 71.5(3) . . . . ? C1 N1 Si1 C6 34.7(3) . . . . ? B1 N1 Si1 C6 -152.6(2) . . . . ? C1 N1 Si1 C8 154.1(2) . . . . ? B1 N1 Si1 C8 -33.3(3) . . . . ? C1 N1 Si1 C7 -86.7(3) . . . . ? B1 N1 Si1 C7 85.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.462 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.083 data_nhnh025 _database_code_depnum_ccdc_archive 'CCDC 275325' _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; _publ_section_references ; Allen, F.H. (2002). Acta Cryst. B58, 380-388. Cremer D. & Pople J.A. (1975). J. Am. Chem. Soc. 97, 1358-1367. Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. ; #3. data _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H31 B Br2 Fe N2' _chemical_formula_sum 'C23 H31 B Br2 Fe N2' _chemical_formula_weight 561.98 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.953(5) _cell_length_b 10.716(5) _cell_length_c 15.723(5) _cell_angle_alpha 90 _cell_angle_beta 103.837(5) _cell_angle_gamma 90 _cell_volume 2282.7(15) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.635 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 4.174 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.3674 _exptl_absorpt_correction_T_max 0.3674 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8684 _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_sigmaI/netI 0.0831 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4966 _reflns_number_gt 3181 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement Denzo _computing_data_reduction Scalepack _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0355P)^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_number_reflns 4966 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0927 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.0855 _refine_ls_wR_factor_gt 0.0742 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 C1 C 0.2852(2) -0.0844(3) 0.4745(2) 0.0182(7) Uani 1 1 d . . . C2 C 0.1223(2) -0.0359(3) 0.3633(2) 0.0218(8) Uani 1 1 d . . . H2 H 0.0965 -0.1208 0.3720 0.026 Uiso 1 1 calc R . . C3 C 0.1462(2) -0.0337(3) 0.2745(2) 0.0245(8) Uani 1 1 d . . . H3A H 0.1978 -0.0966 0.2730 0.029 Uiso 1 1 calc R . . H3B H 0.1725 0.0494 0.2644 0.029 Uiso 1 1 calc R . . C4 C 0.0546(2) -0.0617(3) 0.2021(2) 0.0246(8) Uani 1 1 d . . . H4A H 0.0714 -0.0580 0.1444 0.030 Uiso 1 1 calc R . . H4B H 0.0307 -0.1469 0.2099 0.030 Uiso 1 1 calc R . . C5 C -0.0259(3) 0.0321(4) 0.2044(2) 0.0410(11) Uani 1 1 d . . . H5A H -0.0041 0.1162 0.1910 0.049 Uiso 1 1 calc R . . H5B H -0.0860 0.0105 0.1591 0.049 Uiso 1 1 calc R . . C6 C -0.0493(3) 0.0339(5) 0.2920(2) 0.0611(15) Uani 1 1 d . . . H6A H -0.0788 -0.0472 0.3020 0.073 Uiso 1 1 calc R . . H6B H -0.0989 0.0997 0.2927 0.073 Uiso 1 1 calc R . . C7 C 0.0420(2) 0.0579(4) 0.3666(2) 0.0449(12) Uani 1 1 d . . . H7A H 0.0668 0.1434 0.3614 0.054 Uiso 1 1 calc R . . H7B H 0.0239 0.0514 0.4236 0.054 Uiso 1 1 calc R . . C8 C 0.4262(2) -0.0104(3) 0.6004(2) 0.0224(8) Uani 1 1 d . . . H8 H 0.4736 -0.0726 0.5864 0.027 Uiso 1 1 calc R . . C9 C 0.3939(2) -0.0554(3) 0.6814(2) 0.0254(8) Uani 1 1 d . . . H9A H 0.3432 0.0019 0.6936 0.030 Uiso 1 1 calc R . . H9B H 0.3640 -0.1394 0.6701 0.030 Uiso 1 1 calc R . . C10 C 0.4813(2) -0.0608(4) 0.7613(2) 0.0347(10) Uani 1 1 d . . . H10A H 0.4577 -0.0850 0.8136 0.042 Uiso 1 1 calc R . . H10B H 0.5288 -0.1250 0.7518 0.042 Uiso 1 1 calc R . . C11 C 0.5329(3) 0.0654(4) 0.7771(2) 0.0373(10) Uani 1 1 d . . . H11A H 0.4874 0.1279 0.7921 0.045 Uiso 1 1 calc R . . H11B H 0.5912 0.0589 0.8272 0.045 Uiso 1 1 calc R . . C12 C 0.5652(2) 0.1076(4) 0.6972(2) 0.0358(10) Uani 1 1 d . . . H12A H 0.6146 0.0484 0.6850 0.043 Uiso 1 1 calc R . . H12B H 0.5969 0.1906 0.7085 0.043 Uiso 1 1 calc R . . C13 C 0.4782(2) 0.1157(3) 0.6172(2) 0.0265(9) Uani 1 1 d . . . H13A H 0.4310 0.1799 0.6272 0.032 Uiso 1 1 calc R . . H13B H 0.5021 0.1406 0.5653 0.032 Uiso 1 1 calc R . . C14 C 0.3009(2) -0.2165(3) 0.4627(2) 0.0178(7) Uani 1 1 d . . . C15 C 0.2445(2) -0.2971(3) 0.3964(2) 0.0212(8) Uani 1 1 d . . . H15 H 0.1874 -0.2711 0.3480 0.025 Uiso 1 1 calc R . . C16 C 0.2824(2) -0.4188(3) 0.4111(2) 0.0242(8) Uani 1 1 d . . . H16 H 0.2560 -0.4942 0.3758 0.029 Uiso 1 1 calc R . . C17 C 0.3623(2) -0.4171(3) 0.4858(2) 0.0240(8) Uani 1 1 d . . . H17 H 0.4018 -0.4914 0.5124 0.029 Uiso 1 1 calc R . . C18 C 0.3754(2) -0.2937(3) 0.5183(2) 0.0197(8) Uani 1 1 d . . . H18 H 0.4262 -0.2651 0.5708 0.024 Uiso 1 1 calc R . . C19 C 0.1477(3) -0.2690(4) 0.5859(3) 0.0391(10) Uani 1 1 d . . . H19 H 0.1410 -0.1771 0.5934 0.047 Uiso 1 1 calc R . . C20 C 0.0906(2) -0.3419(4) 0.5180(3) 0.0394(10) Uani 1 1 d . . . H20 H 0.0360 -0.3111 0.4691 0.047 Uiso 1 1 calc R . . C21 C 0.1239(2) -0.4668(4) 0.5318(3) 0.0351(10) Uani 1 1 d . . . H21 H 0.0972 -0.5397 0.4937 0.042 Uiso 1 1 calc R . . C22 C 0.2015(2) -0.4706(3) 0.6077(2) 0.0303(9) Uani 1 1 d . . . H22 H 0.2394 -0.5465 0.6332 0.036 Uiso 1 1 calc R . . C23 C 0.2158(3) -0.3479(4) 0.6418(2) 0.0359(10) Uani 1 1 d . . . H23 H 0.2659 -0.3216 0.6956 0.043 Uiso 1 1 calc R . . B1 B 0.2627(3) 0.0994(4) 0.4866(3) 0.0255(9) Uani 1 1 d . . . N1 N 0.20833(18) -0.0129(2) 0.43503(17) 0.0206(6) Uani 1 1 d . . . N2 N 0.34245(18) 0.0009(2) 0.52411(17) 0.0201(7) Uani 1 1 d . . . Fe1 Fe 0.23616(3) -0.35288(5) 0.51707(3) 0.01981(13) Uani 1 1 d . . . Br1 Br 0.30591(3) 0.22952(4) 0.41157(3) 0.04203(14) Uani 1 1 d . . . Br2 Br 0.19508(3) 0.17790(4) 0.57254(3) 0.04014(13) 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 C1 0.0194(17) 0.0223(19) 0.0148(18) 0.0025(16) 0.0076(15) -0.0044(16) C2 0.0243(18) 0.0206(18) 0.0188(19) -0.0010(16) 0.0019(16) 0.0013(16) C3 0.0226(17) 0.025(2) 0.025(2) 0.0025(17) 0.0044(16) 0.0006(16) C4 0.0237(18) 0.031(2) 0.0187(19) -0.0007(17) 0.0034(16) -0.0020(17) C5 0.037(2) 0.047(3) 0.030(2) -0.009(2) -0.0105(19) 0.011(2) C6 0.030(2) 0.116(4) 0.032(3) -0.031(3) -0.002(2) 0.032(3) C7 0.034(2) 0.070(3) 0.026(2) -0.015(2) -0.0029(19) 0.022(2) C8 0.0216(17) 0.0214(19) 0.023(2) -0.0067(16) 0.0019(16) -0.0017(16) C9 0.0289(19) 0.025(2) 0.023(2) -0.0013(17) 0.0065(16) -0.0006(16) C10 0.035(2) 0.045(3) 0.021(2) 0.0000(19) 0.0015(18) 0.007(2) C11 0.029(2) 0.051(3) 0.026(2) -0.011(2) -0.0047(18) 0.006(2) C12 0.0251(19) 0.039(2) 0.041(3) -0.017(2) 0.0033(19) -0.0082(18) C13 0.0219(17) 0.029(2) 0.027(2) -0.0046(17) 0.0035(16) -0.0080(16) C14 0.0211(17) 0.0150(18) 0.0174(18) 0.0000(15) 0.0051(15) 0.0019(15) C15 0.0240(18) 0.0206(19) 0.0172(18) -0.0027(16) 0.0014(15) 0.0002(16) C16 0.0265(19) 0.023(2) 0.022(2) -0.0023(16) 0.0045(17) -0.0011(16) C17 0.0245(18) 0.023(2) 0.025(2) 0.0028(17) 0.0082(17) 0.0067(16) C18 0.0185(16) 0.023(2) 0.0172(18) -0.0003(15) 0.0031(15) -0.0046(15) C19 0.043(2) 0.030(2) 0.057(3) -0.001(2) 0.036(2) 0.006(2) C20 0.0225(19) 0.049(3) 0.051(3) 0.011(2) 0.0171(19) 0.004(2) C21 0.029(2) 0.035(2) 0.043(3) 0.000(2) 0.011(2) -0.0120(19) C22 0.032(2) 0.025(2) 0.038(2) 0.0078(18) 0.0157(19) -0.0034(17) C23 0.043(2) 0.047(3) 0.023(2) -0.004(2) 0.0173(19) -0.013(2) B1 0.033(2) 0.017(2) 0.025(2) 0.0004(19) 0.004(2) 0.0002(19) N1 0.0234(14) 0.0145(15) 0.0197(16) 0.0000(13) -0.0032(13) 0.0019(13) N2 0.0206(14) 0.0157(15) 0.0208(16) -0.0018(13) -0.0013(13) -0.0024(13) Fe1 0.0201(3) 0.0185(3) 0.0213(3) -0.0001(2) 0.0059(2) -0.0010(2) Br1 0.0552(3) 0.0229(2) 0.0452(3) 0.01065(19) 0.0064(2) -0.00700(19) Br2 0.0447(2) 0.0388(3) 0.0347(2) -0.01090(19) 0.00502(19) 0.0130(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 C1 N2 1.336(4) . ? C1 N1 1.344(4) . ? C1 C14 1.451(4) . ? C2 N1 1.458(4) . ? C2 C3 1.512(4) . ? C2 C7 1.515(5) . ? C2 H2 1.0000 . ? C3 C4 1.525(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.514(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.490(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.533(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N2 1.465(4) . ? C8 C13 1.527(4) . ? C8 C9 1.527(4) . ? C8 H8 1.0000 . ? C9 C10 1.528(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.525(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.502(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.527(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.435(4) . ? C14 C18 1.447(4) . ? C14 Fe1 2.013(3) . ? C15 C16 1.405(5) . ? C15 Fe1 2.018(3) . ? C15 H15 1.0000 . ? C16 C17 1.413(4) . ? C16 Fe1 2.050(3) . ? C16 H16 1.0000 . ? C17 C18 1.414(5) . ? C17 Fe1 2.057(3) . ? C17 H17 1.0000 . ? C18 Fe1 2.039(3) . ? C18 H18 1.0000 . ? C19 C20 1.405(5) . ? C19 C23 1.411(5) . ? C19 Fe1 2.034(4) . ? C19 H19 1.0000 . ? C20 C21 1.417(5) . ? C20 Fe1 2.038(3) . ? C20 H20 1.0000 . ? C21 C22 1.407(5) . ? C21 Fe1 2.042(4) . ? C21 H21 1.0000 . ? C22 C23 1.416(5) . ? C22 Fe1 2.046(4) . ? C22 H22 1.0000 . ? C23 Fe1 2.049(4) . ? C23 H23 1.0000 . ? B1 N2 1.544(5) . ? B1 N1 1.545(5) . ? B1 Br2 2.009(4) . ? B1 Br1 2.009(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 100.3(3) . . ? N2 C1 C14 131.0(3) . . ? N1 C1 C14 128.7(3) . . ? N1 C2 C3 112.9(3) . . ? N1 C2 C7 109.9(3) . . ? C3 C2 C7 110.5(3) . . ? N1 C2 H2 107.8 . . ? C3 C2 H2 107.8 . . ? C7 C2 H2 107.8 . . ? C2 C3 C4 110.8(3) . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C5 C4 C3 110.2(3) . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C6 C5 C4 111.1(3) . . ? C6 C5 H5A 109.4 . . ? C4 C5 H5A 109.4 . . ? C6 C5 H5B 109.4 . . ? C4 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? C5 C6 C7 112.5(3) . . ? C5 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? C5 C6 H6B 109.1 . . ? C7 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? C2 C7 C6 110.4(3) . . ? C2 C7 H7A 109.6 . . ? C6 C7 H7A 109.6 . . ? C2 C7 H7B 109.6 . . ? C6 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? N2 C8 C13 108.7(3) . . ? N2 C8 C9 111.9(2) . . ? C13 C8 C9 110.9(3) . . ? N2 C8 H8 108.4 . . ? C13 C8 H8 108.4 . . ? C9 C8 H8 108.4 . . ? C10 C9 C8 111.2(3) . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9B 109.4 . . ? C8 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C11 C10 C9 110.7(3) . . ? C11 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C12 C11 C10 110.8(3) . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C11 C12 C13 111.6(3) . . ? C11 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? C11 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? C8 C13 C12 110.1(3) . . ? C8 C13 H13A 109.6 . . ? C12 C13 H13A 109.6 . . ? C8 C13 H13B 109.6 . . ? C12 C13 H13B 109.6 . . ? H13A C13 H13B 108.2 . . ? C15 C14 C18 106.6(3) . . ? C15 C14 C1 127.4(3) . . ? C18 C14 C1 126.0(3) . . ? C15 C14 Fe1 69.36(18) . . ? C18 C14 Fe1 70.05(18) . . ? C1 C14 Fe1 123.8(2) . . ? C16 C15 C14 108.6(3) . . ? C16 C15 Fe1 71.0(2) . . ? C14 C15 Fe1 68.94(18) . . ? C16 C15 H15 125.7 . . ? C14 C15 H15 125.7 . . ? Fe1 C15 H15 125.7 . . ? C15 C16 C17 108.5(3) . . ? C15 C16 Fe1 68.61(19) . . ? C17 C16 Fe1 70.14(19) . . ? C15 C16 H16 125.8 . . ? C17 C16 H16 125.8 . . ? Fe1 C16 H16 125.8 . . ? C18 C17 C16 108.6(3) . . ? C18 C17 Fe1 69.13(18) . . ? C16 C17 Fe1 69.61(18) . . ? C18 C17 H17 125.7 . . ? C16 C17 H17 125.7 . . ? Fe1 C17 H17 125.7 . . ? C17 C18 C14 107.7(3) . . ? C17 C18 Fe1 70.48(18) . . ? C14 C18 Fe1 68.12(17) . . ? C17 C18 H18 126.1 . . ? C14 C18 H18 126.1 . . ? Fe1 C18 H18 126.1 . . ? C20 C19 C23 108.4(4) . . ? C20 C19 Fe1 69.9(2) . . ? C23 C19 Fe1 70.3(2) . . ? C20 C19 H19 125.8 . . ? C23 C19 H19 125.8 . . ? Fe1 C19 H19 125.8 . . ? C19 C20 C21 107.7(3) . . ? C19 C20 Fe1 69.68(19) . . ? C21 C20 Fe1 69.8(2) . . ? C19 C20 H20 126.2 . . ? C21 C20 H20 126.2 . . ? Fe1 C20 H20 126.2 . . ? C22 C21 C20 108.3(4) . . ? C22 C21 Fe1 70.03(19) . . ? C20 C21 Fe1 69.5(2) . . ? C22 C21 H21 125.8 . . ? C20 C21 H21 125.8 . . ? Fe1 C21 H21 125.8 . . ? C21 C22 C23 107.7(3) . . ? C21 C22 Fe1 69.7(2) . . ? C23 C22 Fe1 69.9(2) . . ? C21 C22 H22 126.1 . . ? C23 C22 H22 126.1 . . ? Fe1 C22 H22 126.1 . . ? C19 C23 C22 107.9(3) . . ? C19 C23 Fe1 69.2(2) . . ? C22 C23 Fe1 69.7(2) . . ? C19 C23 H23 126.1 . . ? C22 C23 H23 126.1 . . ? Fe1 C23 H23 126.1 . . ? N2 B1 N1 83.5(2) . . ? N2 B1 Br2 116.1(3) . . ? N1 B1 Br2 115.3(2) . . ? N2 B1 Br1 114.1(2) . . ? N1 B1 Br1 114.3(3) . . ? Br2 B1 Br1 111.06(19) . . ? C1 N1 C2 132.8(3) . . ? C1 N1 B1 87.9(2) . . ? C2 N1 B1 138.4(3) . . ? C1 N2 C8 132.0(3) . . ? C1 N2 B1 88.3(2) . . ? C8 N2 B1 136.9(3) . . ? C14 Fe1 C15 41.70(12) . . ? C14 Fe1 C19 107.23(15) . . ? C15 Fe1 C19 123.19(15) . . ? C14 Fe1 C18 41.83(12) . . ? C15 Fe1 C18 69.39(13) . . ? C19 Fe1 C18 123.73(15) . . ? C14 Fe1 C20 120.68(14) . . ? C15 Fe1 C20 105.73(15) . . ? C19 Fe1 C20 40.38(15) . . ? C18 Fe1 C20 158.53(15) . . ? C14 Fe1 C22 161.52(14) . . ? C15 Fe1 C22 155.97(14) . . ? C19 Fe1 C22 68.13(16) . . ? C18 Fe1 C22 124.66(13) . . ? C20 Fe1 C22 68.20(15) . . ? C14 Fe1 C21 156.39(14) . . ? C15 Fe1 C21 120.09(14) . . ? C19 Fe1 C21 67.95(16) . . ? C18 Fe1 C21 159.99(14) . . ? C20 Fe1 C21 40.64(15) . . ? C22 Fe1 C21 40.27(14) . . ? C14 Fe1 C23 124.54(14) . . ? C15 Fe1 C23 160.80(15) . . ? C19 Fe1 C23 40.44(15) . . ? C18 Fe1 C23 109.44(14) . . ? C20 Fe1 C23 67.97(16) . . ? C22 Fe1 C23 40.47(14) . . ? C21 Fe1 C23 67.76(15) . . ? C14 Fe1 C16 69.18(13) . . ? C15 Fe1 C16 40.40(13) . . ? C19 Fe1 C16 158.88(15) . . ? C18 Fe1 C16 68.33(13) . . ? C20 Fe1 C16 122.25(15) . . ? C22 Fe1 C16 121.74(15) . . ? C21 Fe1 C16 106.55(15) . . ? C23 Fe1 C16 158.34(15) . . ? C14 Fe1 C17 69.18(13) . . ? C15 Fe1 C17 68.26(13) . . ? C19 Fe1 C17 159.69(15) . . ? C18 Fe1 C17 40.39(13) . . ? C20 Fe1 C17 158.87(16) . . ? C22 Fe1 C17 108.58(14) . . ? C21 Fe1 C17 123.41(15) . . ? C23 Fe1 C17 124.07(15) . . ? C16 Fe1 C17 40.26(12) . . ? 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 N1 C2 C3 C4 178.5(3) . . . . ? C7 C2 C3 C4 -58.0(4) . . . . ? C2 C3 C4 C5 58.0(4) . . . . ? C3 C4 C5 C6 -56.3(4) . . . . ? C4 C5 C6 C7 55.2(5) . . . . ? N1 C2 C7 C6 -179.4(3) . . . . ? C3 C2 C7 C6 55.4(4) . . . . ? C5 C6 C7 C2 -54.7(5) . . . . ? N2 C8 C9 C10 -177.3(3) . . . . ? C13 C8 C9 C10 -55.7(4) . . . . ? C8 C9 C10 C11 55.6(4) . . . . ? C9 C10 C11 C12 -56.3(4) . . . . ? C10 C11 C12 C13 57.6(4) . . . . ? N2 C8 C13 C12 179.2(3) . . . . ? C9 C8 C13 C12 55.8(4) . . . . ? C11 C12 C13 C8 -57.2(4) . . . . ? N2 C1 C14 C15 -167.4(3) . . . . ? N1 C1 C14 C15 10.1(5) . . . . ? N2 C1 C14 C18 15.0(6) . . . . ? N1 C1 C14 C18 -167.5(3) . . . . ? N2 C1 C14 Fe1 103.9(4) . . . . ? N1 C1 C14 Fe1 -78.6(4) . . . . ? C18 C14 C15 C16 0.4(4) . . . . ? C1 C14 C15 C16 -177.6(3) . . . . ? Fe1 C14 C15 C16 -60.1(2) . . . . ? C18 C14 C15 Fe1 60.5(2) . . . . ? C1 C14 C15 Fe1 -117.5(3) . . . . ? C14 C15 C16 C17 -0.1(4) . . . . ? Fe1 C15 C16 C17 -59.0(2) . . . . ? C14 C15 C16 Fe1 58.9(2) . . . . ? C15 C16 C17 C18 -0.2(4) . . . . ? Fe1 C16 C17 C18 -58.2(2) . . . . ? C15 C16 C17 Fe1 58.0(2) . . . . ? C16 C17 C18 C14 0.4(4) . . . . ? Fe1 C17 C18 C14 -58.1(2) . . . . ? C16 C17 C18 Fe1 58.5(2) . . . . ? C15 C14 C18 C17 -0.5(4) . . . . ? C1 C14 C18 C17 177.5(3) . . . . ? Fe1 C14 C18 C17 59.6(2) . . . . ? C15 C14 C18 Fe1 -60.1(2) . . . . ? C1 C14 C18 Fe1 117.9(3) . . . . ? C23 C19 C20 C21 -0.3(4) . . . . ? Fe1 C19 C20 C21 59.8(3) . . . . ? C23 C19 C20 Fe1 -60.1(2) . . . . ? C19 C20 C21 C22 -0.2(4) . . . . ? Fe1 C20 C21 C22 59.5(3) . . . . ? C19 C20 C21 Fe1 -59.7(2) . . . . ? C20 C21 C22 C23 0.6(4) . . . . ? Fe1 C21 C22 C23 59.8(2) . . . . ? C20 C21 C22 Fe1 -59.2(3) . . . . ? C20 C19 C23 C22 0.7(4) . . . . ? Fe1 C19 C23 C22 -59.1(3) . . . . ? C20 C19 C23 Fe1 59.8(3) . . . . ? C21 C22 C23 C19 -0.8(4) . . . . ? Fe1 C22 C23 C19 58.9(2) . . . . ? C21 C22 C23 Fe1 -59.7(3) . . . . ? N2 C1 N1 C2 170.7(3) . . . . ? C14 C1 N1 C2 -7.3(6) . . . . ? N2 C1 N1 B1 0.1(3) . . . . ? C14 C1 N1 B1 -178.0(4) . . . . ? C3 C2 N1 C1 -76.6(4) . . . . ? C7 C2 N1 C1 159.6(3) . . . . ? C3 C2 N1 B1 89.3(5) . . . . ? C7 C2 N1 B1 -34.5(5) . . . . ? N2 B1 N1 C1 -0.1(2) . . . . ? Br2 B1 N1 C1 -115.9(3) . . . . ? Br1 B1 N1 C1 113.5(3) . . . . ? N2 B1 N1 C2 -169.7(4) . . . . ? Br2 B1 N1 C2 74.4(5) . . . . ? Br1 B1 N1 C2 -56.2(5) . . . . ? N1 C1 N2 C8 162.6(3) . . . . ? C14 C1 N2 C8 -19.3(6) . . . . ? N1 C1 N2 B1 -0.1(3) . . . . ? C14 C1 N2 B1 177.9(4) . . . . ? C13 C8 N2 C1 166.8(3) . . . . ? C9 C8 N2 C1 -70.3(4) . . . . ? C13 C8 N2 B1 -38.9(5) . . . . ? C9 C8 N2 B1 84.0(4) . . . . ? N1 B1 N2 C1 0.1(2) . . . . ? Br2 B1 N2 C1 115.2(3) . . . . ? Br1 B1 N2 C1 -113.7(3) . . . . ? N1 B1 N2 C8 -161.1(3) . . . . ? Br2 B1 N2 C8 -46.0(5) . . . . ? Br1 B1 N2 C8 85.2(4) . . . . ? C18 C14 Fe1 C15 -117.4(3) . . . . ? C1 C14 Fe1 C15 121.9(3) . . . . ? C15 C14 Fe1 C19 -120.9(2) . . . . ? C18 C14 Fe1 C19 121.7(2) . . . . ? C1 C14 Fe1 C19 1.0(3) . . . . ? C15 C14 Fe1 C18 117.4(3) . . . . ? C1 C14 Fe1 C18 -120.7(3) . . . . ? C15 C14 Fe1 C20 -78.9(2) . . . . ? C18 C14 Fe1 C20 163.7(2) . . . . ? C1 C14 Fe1 C20 43.0(3) . . . . ? C15 C14 Fe1 C22 166.7(4) . . . . ? C18 C14 Fe1 C22 49.3(5) . . . . ? C1 C14 Fe1 C22 -71.4(5) . . . . ? C15 C14 Fe1 C21 -46.7(4) . . . . ? C18 C14 Fe1 C21 -164.1(3) . . . . ? C1 C14 Fe1 C21 75.2(5) . . . . ? C15 C14 Fe1 C23 -161.97(19) . . . . ? C18 C14 Fe1 C23 80.6(2) . . . . ? C1 C14 Fe1 C23 -40.1(3) . . . . ? C15 C14 Fe1 C16 37.06(17) . . . . ? C18 C14 Fe1 C16 -80.36(19) . . . . ? C1 C14 Fe1 C16 159.0(3) . . . . ? C15 C14 Fe1 C17 80.27(19) . . . . ? C18 C14 Fe1 C17 -37.16(18) . . . . ? C1 C14 Fe1 C17 -157.8(3) . . . . ? C16 C15 Fe1 C14 119.6(3) . . . . ? C16 C15 Fe1 C19 -162.0(2) . . . . ? C14 C15 Fe1 C19 78.3(2) . . . . ? C16 C15 Fe1 C18 80.4(2) . . . . ? C14 C15 Fe1 C18 -39.23(17) . . . . ? C16 C15 Fe1 C20 -121.6(2) . . . . ? C14 C15 Fe1 C20 118.7(2) . . . . ? C16 C15 Fe1 C22 -50.0(4) . . . . ? C14 C15 Fe1 C22 -169.7(3) . . . . ? C16 C15 Fe1 C21 -80.0(2) . . . . ? C14 C15 Fe1 C21 160.32(19) . . . . ? C16 C15 Fe1 C23 170.5(4) . . . . ? C14 C15 Fe1 C23 50.8(5) . . . . ? C14 C15 Fe1 C16 -119.6(3) . . . . ? C16 C15 Fe1 C17 36.96(18) . . . . ? C14 C15 Fe1 C17 -82.68(19) . . . . ? C20 C19 Fe1 C14 117.4(2) . . . . ? C23 C19 Fe1 C14 -123.5(2) . . . . ? C20 C19 Fe1 C15 74.4(3) . . . . ? C23 C19 Fe1 C15 -166.5(2) . . . . ? C20 C19 Fe1 C18 160.4(2) . . . . ? C23 C19 Fe1 C18 -80.4(3) . . . . ? C23 C19 Fe1 C20 119.2(3) . . . . ? C20 C19 Fe1 C22 -81.6(2) . . . . ? C23 C19 Fe1 C22 37.5(2) . . . . ? C20 C19 Fe1 C21 -38.0(2) . . . . ? C23 C19 Fe1 C21 81.1(2) . . . . ? C20 C19 Fe1 C23 -119.2(3) . . . . ? C20 C19 Fe1 C16 40.7(5) . . . . ? C23 C19 Fe1 C16 159.8(4) . . . . ? C20 C19 Fe1 C17 -166.2(4) . . . . ? C23 C19 Fe1 C17 -47.0(5) . . . . ? C17 C18 Fe1 C14 -119.4(3) . . . . ? C17 C18 Fe1 C15 -80.3(2) . . . . ? C14 C18 Fe1 C15 39.11(18) . . . . ? C17 C18 Fe1 C19 162.8(2) . . . . ? C14 C18 Fe1 C19 -77.8(2) . . . . ? C17 C18 Fe1 C20 -160.8(4) . . . . ? C14 C18 Fe1 C20 -41.4(5) . . . . ? C17 C18 Fe1 C22 77.6(2) . . . . ? C14 C18 Fe1 C22 -163.0(2) . . . . ? C17 C18 Fe1 C21 41.9(5) . . . . ? C14 C18 Fe1 C21 161.3(4) . . . . ? C17 C18 Fe1 C23 120.1(2) . . . . ? C14 C18 Fe1 C23 -120.5(2) . . . . ? C17 C18 Fe1 C16 -36.84(19) . . . . ? C14 C18 Fe1 C16 82.6(2) . . . . ? C14 C18 Fe1 C17 119.4(3) . . . . ? C19 C20 Fe1 C14 -80.4(3) . . . . ? C21 C20 Fe1 C14 160.8(2) . . . . ? C19 C20 Fe1 C15 -123.1(2) . . . . ? C21 C20 Fe1 C15 118.1(2) . . . . ? C21 C20 Fe1 C19 -118.7(4) . . . . ? C19 C20 Fe1 C18 -49.6(5) . . . . ? C21 C20 Fe1 C18 -168.3(3) . . . . ? C19 C20 Fe1 C22 81.4(3) . . . . ? C21 C20 Fe1 C22 -37.3(2) . . . . ? C19 C20 Fe1 C21 118.7(4) . . . . ? C19 C20 Fe1 C23 37.7(2) . . . . ? C21 C20 Fe1 C23 -81.1(3) . . . . ? C19 C20 Fe1 C16 -163.9(2) . . . . ? C21 C20 Fe1 C16 77.4(3) . . . . ? C19 C20 Fe1 C17 166.7(4) . . . . ? C21 C20 Fe1 C17 48.0(5) . . . . ? C21 C22 Fe1 C14 160.1(4) . . . . ? C23 C22 Fe1 C14 41.3(5) . . . . ? C21 C22 Fe1 C15 -42.0(4) . . . . ? C23 C22 Fe1 C15 -160.8(3) . . . . ? C21 C22 Fe1 C19 81.3(2) . . . . ? C23 C22 Fe1 C19 -37.5(2) . . . . ? C21 C22 Fe1 C18 -162.0(2) . . . . ? C23 C22 Fe1 C18 79.2(3) . . . . ? C21 C22 Fe1 C20 37.6(2) . . . . ? C23 C22 Fe1 C20 -81.2(2) . . . . ? C23 C22 Fe1 C21 -118.8(3) . . . . ? C21 C22 Fe1 C23 118.8(3) . . . . ? C21 C22 Fe1 C16 -77.8(2) . . . . ? C23 C22 Fe1 C16 163.5(2) . . . . ? C21 C22 Fe1 C17 -120.1(2) . . . . ? C23 C22 Fe1 C17 121.1(2) . . . . ? C22 C21 Fe1 C14 -164.4(3) . . . . ? C20 C21 Fe1 C14 -44.8(5) . . . . ? C22 C21 Fe1 C15 161.6(2) . . . . ? C20 C21 Fe1 C15 -78.8(3) . . . . ? C22 C21 Fe1 C19 -81.7(2) . . . . ? C20 C21 Fe1 C19 37.8(2) . . . . ? C22 C21 Fe1 C18 47.9(5) . . . . ? C20 C21 Fe1 C18 167.5(4) . . . . ? C22 C21 Fe1 C20 -119.5(3) . . . . ? C20 C21 Fe1 C22 119.5(3) . . . . ? C22 C21 Fe1 C23 -37.9(2) . . . . ? C20 C21 Fe1 C23 81.6(3) . . . . ? C22 C21 Fe1 C16 119.9(2) . . . . ? C20 C21 Fe1 C16 -120.6(3) . . . . ? C22 C21 Fe1 C17 79.2(3) . . . . ? C20 C21 Fe1 C17 -161.3(2) . . . . ? C19 C23 Fe1 C14 75.3(3) . . . . ? C22 C23 Fe1 C14 -165.3(2) . . . . ? C19 C23 Fe1 C15 36.6(5) . . . . ? C22 C23 Fe1 C15 156.0(4) . . . . ? C22 C23 Fe1 C19 119.4(3) . . . . ? C19 C23 Fe1 C18 119.6(2) . . . . ? C22 C23 Fe1 C18 -121.0(2) . . . . ? C19 C23 Fe1 C20 -37.6(2) . . . . ? C22 C23 Fe1 C20 81.8(2) . . . . ? C19 C23 Fe1 C22 -119.4(3) . . . . ? C19 C23 Fe1 C21 -81.6(2) . . . . ? C22 C23 Fe1 C21 37.7(2) . . . . ? C19 C23 Fe1 C16 -160.3(3) . . . . ? C22 C23 Fe1 C16 -41.0(5) . . . . ? C19 C23 Fe1 C17 162.2(2) . . . . ? C22 C23 Fe1 C17 -78.5(2) . . . . ? C15 C16 Fe1 C14 -38.22(18) . . . . ? C17 C16 Fe1 C14 82.0(2) . . . . ? C17 C16 Fe1 C15 120.2(3) . . . . ? C15 C16 Fe1 C19 45.8(5) . . . . ? C17 C16 Fe1 C19 166.0(4) . . . . ? C15 C16 Fe1 C18 -83.2(2) . . . . ? C17 C16 Fe1 C18 37.0(2) . . . . ? C15 C16 Fe1 C20 75.7(2) . . . . ? C17 C16 Fe1 C20 -164.1(2) . . . . ? C15 C16 Fe1 C22 158.47(19) . . . . ? C17 C16 Fe1 C22 -81.3(2) . . . . ? C15 C16 Fe1 C21 117.2(2) . . . . ? C17 C16 Fe1 C21 -122.5(2) . . . . ? C15 C16 Fe1 C23 -171.5(3) . . . . ? C17 C16 Fe1 C23 -51.3(4) . . . . ? C15 C16 Fe1 C17 -120.2(3) . . . . ? C18 C17 Fe1 C14 38.44(19) . . . . ? C16 C17 Fe1 C14 -82.0(2) . . . . ? C18 C17 Fe1 C15 83.3(2) . . . . ? C16 C17 Fe1 C15 -37.1(2) . . . . ? C18 C17 Fe1 C19 -45.0(5) . . . . ? C16 C17 Fe1 C19 -165.4(4) . . . . ? C16 C17 Fe1 C18 -120.4(3) . . . . ? C18 C17 Fe1 C20 160.5(4) . . . . ? C16 C17 Fe1 C20 40.1(5) . . . . ? C18 C17 Fe1 C22 -122.1(2) . . . . ? C16 C17 Fe1 C22 117.5(2) . . . . ? C18 C17 Fe1 C21 -164.1(2) . . . . ? C16 C17 Fe1 C21 75.5(2) . . . . ? C18 C17 Fe1 C23 -79.9(2) . . . . ? C16 C17 Fe1 C23 159.7(2) . . . . ? C18 C17 Fe1 C16 120.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.706 _refine_diff_density_min -0.637 _refine_diff_density_rms 0.100