# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _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 512-471-7710 _publ_contact_author_fax 512-471-6822 _publ_contact_author_email cowley@mail.utexas.edu 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 ; 'Jennifer A. Moore' ; 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 ; ; _publ_section_title ; Isolation of an intermediate in the insertion of a carbodiimide into a boron-aryl bond ; data_nhnh026 _database_code_depnum_ccdc_archive 'CCDC 278056' _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 'C19 H27 B Cl2 N2' _chemical_formula_sum 'C19 H27 B Cl2 N2' _chemical_formula_weight 365.14 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' 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 _symmetry_space_group_name_Hall -C2yc 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 37.418(5) _cell_length_b 6.561(5) _cell_length_c 15.964(5) _cell_angle_alpha 90 _cell_angle_beta 100.318(5) _cell_angle_gamma 90 _cell_volume 3856(3) _cell_formula_units_Z 8 _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 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 0.340 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9050 _exptl_absorpt_correction_T_max 0.9050 _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 7447 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0798 _diffrn_reflns_limit_h_min -47 _diffrn_reflns_limit_h_max 47 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4205 _reflns_number_gt 2567 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SHELXL-97 (Sheldrick, 1997)' _computing_cell_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_data_reduction 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0589P)^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_coef ? _refine_ls_number_reflns 4205 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1029 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1211 _refine_ls_wR_factor_gt 0.1020 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.002 _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 0.59558(6) 0.0200(4) 0.17569(13) 0.0249(5) Uani 1 1 d . . . C2 C 0.57166(6) 0.1665(4) 0.13411(14) 0.0291(6) Uani 1 1 d . . . H2 H 0.5803 0.2968 0.1266 0.035 Uiso 1 1 calc R . . C3 C 0.53552(6) 0.1238(4) 0.10382(15) 0.0368(7) Uani 1 1 d . . . H3 H 0.5203 0.2252 0.0768 0.044 Uiso 1 1 calc R . . C4 C 0.52186(6) -0.0682(4) 0.11338(15) 0.0375(7) Uani 1 1 d . . . H4 H 0.4976 -0.0973 0.0926 0.045 Uiso 1 1 calc R . . C5 C 0.54465(6) -0.2166(4) 0.15404(15) 0.0369(6) Uani 1 1 d . . . H5 H 0.5356 -0.3462 0.1613 0.044 Uiso 1 1 calc R . . C6 C 0.58092(6) -0.1741(4) 0.18418(14) 0.0307(6) Uani 1 1 d . . . H6 H 0.5959 -0.2769 0.2107 0.037 Uiso 1 1 calc R . . C7 C 0.70075(6) 0.0022(4) 0.14948(13) 0.0248(5) Uani 1 1 d . . . H7 H 0.7098 0.0327 0.2097 0.030 Uiso 1 1 calc R . . C8 C 0.71639(6) -0.2030(4) 0.13028(14) 0.0293(6) Uani 1 1 d . . . H8A H 0.7073 -0.2402 0.0715 0.035 Uiso 1 1 calc R . . H8B H 0.7088 -0.3068 0.1667 0.035 Uiso 1 1 calc R . . C9 C 0.75788(6) -0.1919(4) 0.14539(15) 0.0355(6) Uani 1 1 d . . . H9A H 0.7670 -0.1687 0.2054 0.043 Uiso 1 1 calc R . . H9B H 0.7675 -0.3210 0.1299 0.043 Uiso 1 1 calc R . . C10 C 0.77107(6) -0.0217(4) 0.09358(15) 0.0351(6) Uani 1 1 d . . . H10A H 0.7974 -0.0134 0.1072 0.042 Uiso 1 1 calc R . . H10B H 0.7642 -0.0520 0.0334 0.042 Uiso 1 1 calc R . . C11 C 0.75477(6) 0.1808(4) 0.11262(14) 0.0331(6) Uani 1 1 d . . . H11A H 0.7625 0.2855 0.0768 0.040 Uiso 1 1 calc R . . H11B H 0.7637 0.2175 0.1715 0.040 Uiso 1 1 calc R . . C12 C 0.71342(6) 0.1726(4) 0.09724(14) 0.0281(6) Uani 1 1 d . . . H12A H 0.7039 0.3018 0.1130 0.034 Uiso 1 1 calc R . . H12B H 0.7042 0.1494 0.0372 0.034 Uiso 1 1 calc R . . C13 C 0.64318(6) -0.0624(4) 0.06339(14) 0.0257(5) Uani 1 1 d . . . C14 C 0.61102(6) -0.2550(4) -0.06281(13) 0.0268(6) Uani 1 1 d . . . H14 H 0.6254 -0.2785 -0.1075 0.032 Uiso 1 1 calc R . . C15 C 0.60948(7) -0.4518(4) -0.01434(15) 0.0393(7) Uani 1 1 d . . . H15A H 0.5971 -0.4289 0.0332 0.047 Uiso 1 1 calc R . . H15B H 0.6339 -0.4979 0.0081 0.047 Uiso 1 1 calc R . . C16 C 0.58943(8) -0.6148(4) -0.07278(16) 0.0444(7) Uani 1 1 d . . . H16A H 0.6035 -0.6488 -0.1163 0.053 Uiso 1 1 calc R . . H16B H 0.5872 -0.7370 -0.0399 0.053 Uiso 1 1 calc R . . C17 C 0.55210(7) -0.5448(4) -0.11482(16) 0.0444(7) Uani 1 1 d . . . H17A H 0.5371 -0.5254 -0.0719 0.053 Uiso 1 1 calc R . . H17B H 0.5409 -0.6488 -0.1541 0.053 Uiso 1 1 calc R . . C18 C 0.55428(7) -0.3473(4) -0.16250(15) 0.0386(7) Uani 1 1 d . . . H18A H 0.5299 -0.3018 -0.1865 0.046 Uiso 1 1 calc R . . H18B H 0.5672 -0.3706 -0.2091 0.046 Uiso 1 1 calc R . . C19 C 0.57368(6) -0.1812(4) -0.10432(15) 0.0326(6) Uani 1 1 d . . . H19A H 0.5760 -0.0592 -0.1373 0.039 Uiso 1 1 calc R . . H19B H 0.5596 -0.1476 -0.0608 0.039 Uiso 1 1 calc R . . B1 B 0.63763(7) 0.0636(4) 0.20723(16) 0.0250(6) Uani 1 1 d . . . N1 N 0.66004(5) -0.0051(3) 0.13683(11) 0.0232(4) Uani 1 1 d . . . N2 N 0.62869(5) -0.0940(3) -0.00632(12) 0.0303(5) Uani 1 1 d . . . Cl1 Cl 0.648020(15) 0.34269(9) 0.22718(4) 0.03174(19) Uani 1 1 d . . . Cl2 Cl 0.657311(15) -0.07957(10) 0.30631(3) 0.03173(19) 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 0.0281(13) 0.0277(15) 0.0203(11) -0.0019(11) 0.0085(9) 0.0000(11) C2 0.0291(14) 0.0293(15) 0.0292(13) 0.0032(11) 0.0063(10) 0.0016(11) C3 0.0292(15) 0.0423(19) 0.0368(14) 0.0049(13) 0.0002(11) 0.0060(12) C4 0.0260(14) 0.0477(18) 0.0371(14) 0.0022(13) 0.0012(11) -0.0069(13) C5 0.0319(15) 0.0384(17) 0.0397(15) 0.0042(13) 0.0049(11) -0.0102(13) C6 0.0295(14) 0.0297(16) 0.0320(13) 0.0029(12) 0.0036(10) 0.0033(12) C7 0.0206(13) 0.0299(14) 0.0237(12) -0.0039(11) 0.0037(9) -0.0024(10) C8 0.0312(14) 0.0281(15) 0.0289(13) -0.0022(11) 0.0058(10) -0.0001(11) C9 0.0301(14) 0.0409(18) 0.0352(14) -0.0005(12) 0.0053(11) 0.0086(12) C10 0.0229(14) 0.0541(19) 0.0291(13) 0.0014(13) 0.0066(10) 0.0025(12) C11 0.0296(14) 0.0429(17) 0.0278(13) -0.0003(12) 0.0081(10) -0.0050(12) C12 0.0278(13) 0.0279(15) 0.0293(13) -0.0004(11) 0.0068(10) 0.0004(11) C13 0.0224(13) 0.0272(15) 0.0299(14) 0.0021(11) 0.0110(10) -0.0001(10) C14 0.0299(13) 0.0284(15) 0.0222(12) -0.0041(11) 0.0050(10) -0.0050(11) C15 0.0531(17) 0.0328(17) 0.0309(14) 0.0002(12) 0.0041(12) 0.0062(13) C16 0.068(2) 0.0239(16) 0.0422(16) -0.0007(13) 0.0124(14) -0.0026(14) C17 0.0528(18) 0.0417(19) 0.0407(15) -0.0107(13) 0.0142(13) -0.0207(14) C18 0.0360(15) 0.0389(17) 0.0380(15) -0.0023(13) -0.0012(11) -0.0046(13) C19 0.0349(15) 0.0267(15) 0.0332(13) 0.0002(12) -0.0022(10) -0.0017(11) B1 0.0240(15) 0.0288(17) 0.0222(13) 0.0014(12) 0.0042(10) 0.0011(12) N1 0.0237(11) 0.0236(11) 0.0219(10) -0.0002(9) 0.0029(8) -0.0004(8) N2 0.0288(11) 0.0395(14) 0.0230(11) -0.0022(10) 0.0058(8) -0.0025(10) Cl1 0.0311(4) 0.0285(4) 0.0357(4) -0.0066(3) 0.0064(2) -0.0014(3) Cl2 0.0299(4) 0.0408(4) 0.0244(3) 0.0045(3) 0.0048(2) 0.0024(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 C2 1.397(3) . ? C1 C6 1.403(3) . ? C1 B1 1.590(3) . ? C2 C3 1.381(3) . ? C2 H2 0.9300 . ? C3 C4 1.378(4) . ? C3 H3 0.9300 . ? C4 C5 1.378(3) . ? C4 H4 0.9300 . ? C5 C6 1.384(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.501(3) . ? C7 C8 1.520(3) . ? C7 C12 1.521(3) . ? C7 H7 0.9800 . ? C8 C9 1.530(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.523(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.515(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.523(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N2 1.166(3) . ? C13 N1 1.284(3) . ? C14 N2 1.468(3) . ? C14 C15 1.511(3) . ? C14 C19 1.515(3) . ? C14 H14 0.9800 . ? C15 C16 1.525(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.509(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.513(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.528(3) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? B1 N1 1.583(3) . ? B1 Cl2 1.873(3) . ? B1 Cl1 1.887(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 C2 C1 C6 116.2(2) . . ? C2 C1 B1 122.7(2) . . ? C6 C1 B1 121.0(2) . . ? C3 C2 C1 122.0(2) . . ? C3 C2 H2 119.0 . . ? C1 C2 H2 119.0 . . ? C4 C3 C2 120.4(2) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C5 C4 C3 119.2(2) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 120.5(2) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C1 121.7(2) . . ? C5 C6 H6 119.2 . . ? C1 C6 H6 119.2 . . ? N1 C7 C8 111.27(18) . . ? N1 C7 C12 110.98(18) . . ? C8 C7 C12 111.79(18) . . ? N1 C7 H7 107.5 . . ? C8 C7 H7 107.5 . . ? C12 C7 H7 107.5 . . ? C7 C8 C9 110.03(19) . . ? C7 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? C7 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C10 C9 C8 111.6(2) . . ? C10 C9 H9A 109.3 . . ? C8 C9 H9A 109.3 . . ? C10 C9 H9B 109.3 . . ? C8 C9 H9B 109.3 . . ? H9A C9 H9B 108.0 . . ? C11 C10 C9 110.6(2) . . ? 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 . . ? C10 C11 C12 111.7(2) . . ? C10 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? C10 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 107.9 . . ? C7 C12 C11 110.18(19) . . ? C7 C12 H12A 109.6 . . ? C11 C12 H12A 109.6 . . ? C7 C12 H12B 109.6 . . ? C11 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? N2 C13 N1 172.7(3) . . ? N2 C14 C15 110.79(18) . . ? N2 C14 C19 108.51(19) . . ? C15 C14 C19 112.35(19) . . ? N2 C14 H14 108.4 . . ? C15 C14 H14 108.4 . . ? C19 C14 H14 108.4 . . ? C14 C15 C16 110.2(2) . . ? C14 C15 H15A 109.6 . . ? C16 C15 H15A 109.6 . . ? C14 C15 H15B 109.6 . . ? C16 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? C17 C16 C15 111.9(2) . . ? C17 C16 H16A 109.2 . . ? C15 C16 H16A 109.2 . . ? C17 C16 H16B 109.2 . . ? C15 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C16 C17 C18 110.8(2) . . ? C16 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? C17 C18 C19 111.6(2) . . ? C17 C18 H18A 109.3 . . ? C19 C18 H18A 109.3 . . ? C17 C18 H18B 109.3 . . ? C19 C18 H18B 109.3 . . ? H18A C18 H18B 108.0 . . ? C14 C19 C18 109.8(2) . . ? C14 C19 H19A 109.7 . . ? C18 C19 H19A 109.7 . . ? C14 C19 H19B 109.7 . . ? C18 C19 H19B 109.7 . . ? H19A C19 H19B 108.2 . . ? N1 B1 C1 110.11(18) . . ? N1 B1 Cl2 106.16(16) . . ? C1 B1 Cl2 113.22(17) . . ? N1 B1 Cl1 106.07(16) . . ? C1 B1 Cl1 112.98(17) . . ? Cl2 B1 Cl1 107.83(13) . . ? C13 N1 C7 116.93(17) . . ? C13 N1 B1 119.70(18) . . ? C7 N1 B1 123.30(17) . . ? C13 N2 C14 142.7(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 C6 C1 C2 C3 0.7(3) . . . . ? B1 C1 C2 C3 177.2(2) . . . . ? C1 C2 C3 C4 -0.5(4) . . . . ? C2 C3 C4 C5 0.4(4) . . . . ? C3 C4 C5 C6 -0.7(4) . . . . ? C4 C5 C6 C1 0.9(4) . . . . ? C2 C1 C6 C5 -0.9(3) . . . . ? B1 C1 C6 C5 -177.4(2) . . . . ? N1 C7 C8 C9 -178.91(17) . . . . ? C12 C7 C8 C9 56.4(2) . . . . ? C7 C8 C9 C10 -55.8(3) . . . . ? C8 C9 C10 C11 55.7(3) . . . . ? C9 C10 C11 C12 -55.9(3) . . . . ? N1 C7 C12 C11 178.60(18) . . . . ? C8 C7 C12 C11 -56.5(2) . . . . ? C10 C11 C12 C7 56.1(3) . . . . ? N2 C14 C15 C16 177.3(2) . . . . ? C19 C14 C15 C16 55.7(3) . . . . ? C14 C15 C16 C17 -55.0(3) . . . . ? C15 C16 C17 C18 55.5(3) . . . . ? C16 C17 C18 C19 -56.1(3) . . . . ? N2 C14 C19 C18 -179.03(18) . . . . ? C15 C14 C19 C18 -56.2(3) . . . . ? C17 C18 C19 C14 56.0(3) . . . . ? C2 C1 B1 N1 -93.5(3) . . . . ? C6 C1 B1 N1 82.8(3) . . . . ? C2 C1 B1 Cl2 147.81(19) . . . . ? C6 C1 B1 Cl2 -35.9(3) . . . . ? C2 C1 B1 Cl1 24.9(3) . . . . ? C6 C1 B1 Cl1 -158.82(18) . . . . ? C8 C7 N1 C13 -56.1(3) . . . . ? C12 C7 N1 C13 69.1(3) . . . . ? C8 C7 N1 B1 126.9(2) . . . . ? C12 C7 N1 B1 -107.9(2) . . . . ? C1 B1 N1 C13 7.5(3) . . . . ? Cl2 B1 N1 C13 130.4(2) . . . . ? Cl1 B1 N1 C13 -115.1(2) . . . . ? C1 B1 N1 C7 -175.59(19) . . . . ? Cl2 B1 N1 C7 -52.7(2) . . . . ? Cl1 B1 N1 C7 61.8(2) . . . . ? C15 C14 N2 C13 2.9(4) . . . . ? C19 C14 N2 C13 126.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.464 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.065 data_nhnh039 _database_code_depnum_ccdc_archive 'CCDC 278734' _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 ; ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H27 B Cl2 N2' _chemical_formula_sum 'C19 H27 B Cl2 N2' _chemical_formula_weight 365.14 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.355(5) _cell_length_b 11.914(5) _cell_length_c 16.592(5) _cell_angle_alpha 73.933(5) _cell_angle_beta 83.657(5) _cell_angle_gamma 80.431(5) _cell_volume 1935.1(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 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 1.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.338 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9255 _exptl_absorpt_correction_T_max 0.9354 _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 12839 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0919 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.28 _diffrn_reflns_theta_max 27.57 _reflns_number_total 8720 _reflns_number_gt 5120 _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^)+(0.0664P)^2^+0.0155P] 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 8720 _refine_ls_number_parameters 433 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1133 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1417 _refine_ls_wR_factor_gt 0.1167 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 0.7500(2) 0.3219(2) 0.92445(15) 0.0291(5) Uani 1 1 d . . . C2 C 0.8827(2) 0.3543(2) 0.91340(15) 0.0297(6) Uani 1 1 d . . . C3 C 0.9922(2) 0.2700(2) 0.90947(16) 0.0395(7) Uani 1 1 d . . . H3 H 0.9818 0.1926 0.9133 0.047 Uiso 1 1 calc R . . C4 C 1.1167(3) 0.3024(3) 0.89976(18) 0.0513(8) Uani 1 1 d . . . H4 H 1.1901 0.2465 0.8969 0.062 Uiso 1 1 calc R . . C5 C 1.1319(3) 0.4166(3) 0.89439(18) 0.0530(8) Uani 1 1 d . . . H5 H 1.2156 0.4379 0.8880 0.064 Uiso 1 1 calc R . . C6 C 1.0233(3) 0.4998(3) 0.89848(17) 0.0467(7) Uani 1 1 d . . . H6 H 1.0340 0.5771 0.8948 0.056 Uiso 1 1 calc R . . C7 C 0.8987(2) 0.4689(2) 0.90796(15) 0.0361(6) Uani 1 1 d . . . H7 H 0.8256 0.5252 0.9107 0.043 Uiso 1 1 calc R . . C8 C 0.6420(2) 0.4559(2) 0.79653(15) 0.0316(6) Uani 1 1 d . . . H8 H 0.7000 0.5151 0.7913 0.038 Uiso 1 1 calc R . . C9 C 0.5027(2) 0.5192(2) 0.78326(16) 0.0405(7) Uani 1 1 d . . . H9A H 0.4769 0.5653 0.8238 0.049 Uiso 1 1 calc R . . H9B H 0.4429 0.4616 0.7923 0.049 Uiso 1 1 calc R . . C10 C 0.4931(3) 0.6003(2) 0.69458(17) 0.0463(7) Uani 1 1 d . . . H10A H 0.4032 0.6381 0.6870 0.056 Uiso 1 1 calc R . . H10B H 0.5480 0.6615 0.6870 0.056 Uiso 1 1 calc R . . C11 C 0.5362(2) 0.5323(2) 0.62942(17) 0.0418(7) Uani 1 1 d . . . H11A H 0.5323 0.5862 0.5737 0.050 Uiso 1 1 calc R . . H11B H 0.4769 0.4755 0.6339 0.050 Uiso 1 1 calc R . . C12 C 0.6754(3) 0.4682(3) 0.64166(16) 0.0441(7) Uani 1 1 d . . . H12A H 0.7358 0.5257 0.6303 0.053 Uiso 1 1 calc R . . H12B H 0.6987 0.4207 0.6019 0.053 Uiso 1 1 calc R . . C13 C 0.6889(2) 0.3893(2) 0.73061(16) 0.0384(6) Uani 1 1 d . . . H13A H 0.6384 0.3248 0.7390 0.046 Uiso 1 1 calc R . . H13B H 0.7803 0.3556 0.7375 0.046 Uiso 1 1 calc R . . C14 C 0.7441(2) 0.1669(2) 1.06241(15) 0.0328(6) Uani 1 1 d . . . H14 H 0.8378 0.1375 1.0556 0.039 Uiso 1 1 calc R . . C15 C 0.6703(3) 0.0614(2) 1.09532(16) 0.0408(7) Uani 1 1 d . . . H15A H 0.6914 0.0099 1.0581 0.049 Uiso 1 1 calc R . . H15B H 0.5767 0.0886 1.0955 0.049 Uiso 1 1 calc R . . C16 C 0.7052(3) -0.0079(3) 1.18400(18) 0.0560(8) Uani 1 1 d . . . H16A H 0.6515 -0.0708 1.2045 0.067 Uiso 1 1 calc R . . H16B H 0.7964 -0.0437 1.1827 0.067 Uiso 1 1 calc R . . C17 C 0.6839(3) 0.0702(3) 1.24309(18) 0.0567(8) Uani 1 1 d . . . H17A H 0.7099 0.0243 1.2984 0.068 Uiso 1 1 calc R . . H17B H 0.5915 0.1010 1.2481 0.068 Uiso 1 1 calc R . . C18 C 0.7632(3) 0.1718(3) 1.21132(18) 0.0477(7) Uani 1 1 d . . . H18A H 0.8561 0.1412 1.2099 0.057 Uiso 1 1 calc R . . H18B H 0.7466 0.2222 1.2494 0.057 Uiso 1 1 calc R . . C19 C 0.7267(3) 0.2435(2) 1.12364(17) 0.0451(7) Uani 1 1 d . . . H19A H 0.6361 0.2804 1.1263 0.054 Uiso 1 1 calc R . . H19B H 0.7815 0.3056 1.1033 0.054 Uiso 1 1 calc R . . C20 C -0.2398(2) 0.16581(19) 0.57873(15) 0.0261(5) Uani 1 1 d . . . C21 C -0.3757(2) 0.17231(19) 0.55697(16) 0.0285(6) Uani 1 1 d . . . C22 C -0.3979(2) 0.1419(2) 0.48541(16) 0.0338(6) Uani 1 1 d . . . H22 H -0.3274 0.1202 0.4504 0.041 Uiso 1 1 calc R . . C23 C -0.5252(3) 0.1440(2) 0.46598(18) 0.0419(7) Uani 1 1 d . . . H23 H -0.5403 0.1236 0.4180 0.050 Uiso 1 1 calc R . . C24 C -0.6294(3) 0.1766(2) 0.5182(2) 0.0477(8) Uani 1 1 d . . . H24 H -0.7148 0.1777 0.5053 0.057 Uiso 1 1 calc R . . C25 C -0.6081(2) 0.2076(2) 0.58916(19) 0.0453(7) Uani 1 1 d . . . H25 H -0.6790 0.2304 0.6235 0.054 Uiso 1 1 calc R . . C26 C -0.4810(2) 0.2047(2) 0.60935(17) 0.0373(6) Uani 1 1 d . . . H26 H -0.4662 0.2244 0.6577 0.045 Uiso 1 1 calc R . . C27 C -0.1211(2) 0.2733(2) 0.44323(15) 0.0298(6) Uani 1 1 d . . . H27 H -0.1655 0.2433 0.4059 0.036 Uiso 1 1 calc R . . C28 C 0.0243(2) 0.2663(2) 0.41452(16) 0.0330(6) Uani 1 1 d . . . H28A H 0.0708 0.2908 0.4529 0.040 Uiso 1 1 calc R . . H28B H 0.0601 0.1853 0.4157 0.040 Uiso 1 1 calc R . . C29 C 0.0450(3) 0.3448(2) 0.32599(17) 0.0396(6) Uani 1 1 d . . . H29A H 0.1382 0.3410 0.3097 0.047 Uiso 1 1 calc R . . H29B H 0.0041 0.3167 0.2868 0.047 Uiso 1 1 calc R . . C30 C -0.0141(2) 0.4717(2) 0.32200(17) 0.0369(6) Uani 1 1 d . . . H30A H -0.0020 0.5204 0.2650 0.044 Uiso 1 1 calc R . . H30B H 0.0308 0.5013 0.3584 0.044 Uiso 1 1 calc R . . C31 C -0.1604(2) 0.4797(2) 0.34937(16) 0.0369(6) Uani 1 1 d . . . H31A H -0.1957 0.5607 0.3484 0.044 Uiso 1 1 calc R . . H31B H -0.2064 0.4560 0.3103 0.044 Uiso 1 1 calc R . . C32 C -0.1827(2) 0.4006(2) 0.43748(16) 0.0335(6) Uani 1 1 d . . . H32A H -0.2762 0.4033 0.4523 0.040 Uiso 1 1 calc R . . H32B H -0.1447 0.4296 0.4773 0.040 Uiso 1 1 calc R . . C33 C -0.2351(2) 0.0457(2) 0.73133(15) 0.0310(6) Uani 1 1 d . . . H33 H -0.3251 0.0776 0.7464 0.037 Uiso 1 1 calc R . . C34 C -0.2356(3) -0.0780(2) 0.72189(16) 0.0390(6) Uani 1 1 d . . . H34A H -0.1490 -0.1077 0.7013 0.047 Uiso 1 1 calc R . . H34B H -0.2970 -0.0744 0.6808 0.047 Uiso 1 1 calc R . . C35 C -0.2743(3) -0.1625(2) 0.80519(17) 0.0435(7) Uani 1 1 d . . . H35A H -0.3638 -0.1367 0.8236 0.052 Uiso 1 1 calc R . . H35B H -0.2704 -0.2409 0.7977 0.052 Uiso 1 1 calc R . . C36 C -0.1827(3) -0.1665(2) 0.87144(18) 0.0487(8) Uani 1 1 d . . . H36A H -0.2095 -0.2193 0.9244 0.058 Uiso 1 1 calc R . . H36B H -0.0941 -0.1970 0.8546 0.058 Uiso 1 1 calc R . . C37 C -0.1851(3) -0.0447(3) 0.88290(17) 0.0476(7) Uani 1 1 d . . . H37A H -0.1236 -0.0486 0.9240 0.057 Uiso 1 1 calc R . . H37B H -0.2721 -0.0174 0.9044 0.057 Uiso 1 1 calc R . . C38 C -0.1493(3) 0.0429(2) 0.80064(16) 0.0393(6) Uani 1 1 d . . . H38A H -0.1589 0.1210 0.8095 0.047 Uiso 1 1 calc R . . H38B H -0.0581 0.0215 0.7832 0.047 Uiso 1 1 calc R . . B1 B 0.5635(3) 0.2865(2) 0.94032(19) 0.0326(7) Uani 1 1 d . . . B2 B -0.0520(3) 0.1493(2) 0.60671(18) 0.0298(6) Uani 1 1 d . . . N1 N 0.64641(17) 0.37786(17) 0.88108(12) 0.0299(5) Uani 1 1 d . . . N2 N 0.69960(18) 0.23347(17) 0.97974(13) 0.0317(5) Uani 1 1 d . . . N3 N -0.13489(17) 0.19666(17) 0.52821(12) 0.0285(5) Uani 1 1 d . . . N4 N -0.18894(17) 0.12531(17) 0.65357(12) 0.0280(5) Uani 1 1 d . . . Cl1 Cl 0.49723(6) 0.19085(6) 0.89061(5) 0.0461(2) Uani 1 1 d . . . Cl2 Cl 0.43732(6) 0.34897(6) 1.00849(4) 0.04311(19) Uani 1 1 d . . . Cl3 Cl 0.06566(6) 0.01614(5) 0.60390(4) 0.03595(17) Uani 1 1 d . . . Cl4 Cl 0.02451(6) 0.25695(6) 0.63757(4) 0.04042(18) 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 0.0251(13) 0.0324(13) 0.0311(14) -0.0096(11) -0.0019(11) -0.0056(10) C2 0.0231(12) 0.0416(15) 0.0244(13) -0.0063(11) -0.0037(10) -0.0079(11) C3 0.0300(14) 0.0468(16) 0.0376(16) -0.0043(13) -0.0046(12) -0.0041(12) C4 0.0234(14) 0.080(2) 0.0429(18) -0.0049(16) -0.0036(12) -0.0023(14) C5 0.0304(16) 0.090(2) 0.0371(18) -0.0013(16) -0.0097(13) -0.0265(16) C6 0.0434(17) 0.0606(19) 0.0398(17) -0.0054(14) -0.0083(13) -0.0281(14) C7 0.0291(14) 0.0497(16) 0.0307(15) -0.0089(12) -0.0035(11) -0.0110(12) C8 0.0294(13) 0.0330(13) 0.0311(14) -0.0043(11) -0.0034(11) -0.0072(11) C9 0.0333(14) 0.0421(15) 0.0406(17) -0.0095(13) -0.0027(12) 0.0073(12) C10 0.0413(16) 0.0410(16) 0.0469(18) 0.0014(14) -0.0099(14) 0.0035(13) C11 0.0376(15) 0.0470(16) 0.0369(16) -0.0007(13) -0.0105(12) -0.0074(12) C12 0.0418(16) 0.0572(18) 0.0319(16) -0.0120(13) -0.0008(12) -0.0038(13) C13 0.0306(14) 0.0463(16) 0.0349(16) -0.0110(13) -0.0024(12) 0.0045(12) C14 0.0238(13) 0.0378(14) 0.0331(15) -0.0028(11) -0.0049(11) -0.0035(10) C15 0.0485(16) 0.0410(15) 0.0348(16) -0.0067(12) -0.0080(13) -0.0140(12) C16 0.067(2) 0.0563(19) 0.0441(19) 0.0067(15) -0.0174(16) -0.0310(16) C17 0.0444(17) 0.093(2) 0.0321(17) -0.0072(16) -0.0079(14) -0.0204(16) C18 0.0425(16) 0.0601(19) 0.0450(18) -0.0195(15) -0.0139(14) -0.0031(14) C19 0.0470(17) 0.0434(16) 0.0481(18) -0.0137(14) -0.0158(14) -0.0040(13) C20 0.0188(11) 0.0277(12) 0.0328(14) -0.0085(10) -0.0037(10) -0.0038(9) C21 0.0211(12) 0.0257(12) 0.0375(15) -0.0040(11) -0.0057(11) -0.0047(9) C22 0.0287(13) 0.0333(13) 0.0387(16) -0.0046(12) -0.0073(12) -0.0071(11) C23 0.0382(16) 0.0377(15) 0.0490(18) 0.0004(13) -0.0176(14) -0.0135(12) C24 0.0235(14) 0.0428(16) 0.070(2) 0.0056(15) -0.0191(14) -0.0112(12) C25 0.0203(13) 0.0495(17) 0.057(2) -0.0005(14) -0.0015(13) -0.0024(12) C26 0.0284(13) 0.0399(15) 0.0404(16) -0.0044(12) -0.0039(12) -0.0052(11) C27 0.0234(12) 0.0334(13) 0.0318(14) -0.0051(11) -0.0017(10) -0.0075(10) C28 0.0247(13) 0.0332(13) 0.0403(16) -0.0108(12) 0.0025(11) -0.0033(10) C29 0.0362(14) 0.0425(15) 0.0404(16) -0.0124(13) 0.0089(12) -0.0116(12) C30 0.0384(15) 0.0358(14) 0.0347(15) -0.0062(12) 0.0050(12) -0.0101(11) C31 0.0353(14) 0.0356(14) 0.0373(16) -0.0037(12) -0.0044(12) -0.0066(11) C32 0.0251(13) 0.0364(14) 0.0356(15) -0.0051(11) -0.0010(11) -0.0032(11) C33 0.0236(12) 0.0356(14) 0.0302(14) -0.0047(11) -0.0001(10) -0.0025(10) C34 0.0395(15) 0.0442(15) 0.0334(15) -0.0081(12) -0.0002(12) -0.0110(12) C35 0.0438(16) 0.0429(16) 0.0406(17) -0.0039(13) 0.0069(13) -0.0156(13) C36 0.0380(16) 0.0494(18) 0.0447(18) 0.0081(14) -0.0012(14) -0.0032(13) C37 0.0466(17) 0.0595(19) 0.0305(16) -0.0033(14) -0.0106(13) 0.0005(14) C38 0.0423(15) 0.0415(15) 0.0348(16) -0.0093(12) -0.0121(12) -0.0029(12) B1 0.0224(14) 0.0376(16) 0.0352(17) -0.0028(13) -0.0042(12) -0.0072(12) B2 0.0205(14) 0.0326(15) 0.0349(17) -0.0062(13) -0.0036(12) -0.0037(11) N1 0.0202(10) 0.0387(12) 0.0312(12) -0.0082(9) -0.0022(9) -0.0068(9) N2 0.0218(10) 0.0342(11) 0.0369(13) -0.0041(10) -0.0039(9) -0.0053(8) N3 0.0191(10) 0.0345(11) 0.0308(12) -0.0053(9) -0.0027(9) -0.0054(8) N4 0.0192(10) 0.0357(11) 0.0290(12) -0.0084(9) -0.0026(8) -0.0036(8) Cl1 0.0377(4) 0.0482(4) 0.0566(5) -0.0119(3) -0.0106(3) -0.0165(3) Cl2 0.0262(3) 0.0564(4) 0.0421(4) -0.0078(3) 0.0015(3) -0.0041(3) Cl3 0.0252(3) 0.0353(3) 0.0457(4) -0.0103(3) -0.0045(3) 0.0012(2) Cl4 0.0292(3) 0.0442(4) 0.0552(5) -0.0219(3) -0.0058(3) -0.0089(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 1.329(3) . ? C1 N1 1.335(3) . ? C1 C2 1.467(3) . ? C2 C7 1.378(3) . ? C2 C3 1.393(3) . ? C3 C4 1.386(4) . ? C3 H3 0.9300 . ? C4 C5 1.374(4) . ? C4 H4 0.9300 . ? C5 C6 1.379(4) . ? C5 H5 0.9300 . ? C6 C7 1.381(3) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 N1 1.453(3) . ? C8 C13 1.516(3) . ? C8 C9 1.522(3) . ? C8 H8 0.9800 . ? C9 C10 1.523(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.511(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.522(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.522(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 N2 1.463(3) . ? C14 C15 1.519(3) . ? C14 C19 1.522(4) . ? C14 H14 0.9800 . ? C15 C16 1.524(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.505(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.516(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.522(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 N3 1.334(3) . ? C20 N4 1.335(3) . ? C20 C21 1.475(3) . ? C21 C22 1.385(3) . ? C21 C26 1.389(3) . ? C22 C23 1.386(3) . ? C22 H22 0.9300 . ? C23 C24 1.381(4) . ? C23 H23 0.9300 . ? C24 C25 1.377(4) . ? C24 H24 0.9300 . ? C25 C26 1.387(3) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 N3 1.459(3) . ? C27 C28 1.524(3) . ? C27 C32 1.526(3) . ? C27 H27 0.9800 . ? C28 C29 1.521(3) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.520(3) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.528(3) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.521(3) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 N4 1.459(3) . ? C33 C38 1.519(3) . ? C33 C34 1.526(3) . ? C33 H33 0.9800 . ? C34 C35 1.525(4) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.515(4) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 C37 1.511(4) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 C38 1.522(4) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? B1 N1 1.556(3) . ? B1 N2 1.579(3) . ? B1 Cl2 1.832(3) . ? B1 Cl1 1.831(3) . ? B2 N3 1.559(3) . ? B2 N4 1.570(3) . ? B2 Cl4 1.824(3) . ? B2 Cl3 1.841(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 101.7(2) . . ? N2 C1 C2 130.5(2) . . ? N1 C1 C2 127.8(2) . . ? C7 C2 C3 120.0(2) . . ? C7 C2 C1 119.5(2) . . ? C3 C2 C1 120.4(2) . . ? C4 C3 C2 119.5(3) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C5 C4 C3 120.2(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.1(3) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C7 120.3(3) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C2 C7 C6 119.9(3) . . ? C2 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? N1 C8 C13 111.6(2) . . ? N1 C8 C9 109.05(19) . . ? C13 C8 C9 111.0(2) . . ? N1 C8 H8 108.4 . . ? C13 C8 H8 108.4 . . ? C9 C8 H8 108.4 . . ? C8 C9 C10 110.8(2) . . ? C8 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C11 C10 C9 111.1(2) . . ? C11 C10 H10A 109.4 . . ? C9 C10 H10A 109.4 . . ? C11 C10 H10B 109.4 . . ? C9 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C10 C11 C12 110.7(2) . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C11 C12 C13 111.5(2) . . ? 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 112.2(2) . . ? C8 C13 H13A 109.2 . . ? C12 C13 H13A 109.2 . . ? C8 C13 H13B 109.2 . . ? C12 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? N2 C14 C15 108.7(2) . . ? N2 C14 C19 111.8(2) . . ? C15 C14 C19 111.4(2) . . ? N2 C14 H14 108.2 . . ? C15 C14 H14 108.2 . . ? C19 C14 H14 108.2 . . ? C14 C15 C16 111.7(2) . . ? C14 C15 H15A 109.3 . . ? C16 C15 H15A 109.3 . . ? C14 C15 H15B 109.3 . . ? C16 C15 H15B 109.3 . . ? H15A C15 H15B 107.9 . . ? C17 C16 C15 111.4(3) . . ? C17 C16 H16A 109.3 . . ? C15 C16 H16A 109.3 . . ? C17 C16 H16B 109.3 . . ? C15 C16 H16B 109.3 . . ? H16A C16 H16B 108.0 . . ? C16 C17 C18 110.7(2) . . ? C16 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? C17 C18 C19 110.6(2) . . ? C17 C18 H18A 109.5 . . ? C19 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C19 C18 H18B 109.5 . . ? H18A C18 H18B 108.1 . . ? C14 C19 C18 111.6(2) . . ? C14 C19 H19A 109.3 . . ? C18 C19 H19A 109.3 . . ? C14 C19 H19B 109.3 . . ? C18 C19 H19B 109.3 . . ? H19A C19 H19B 108.0 . . ? N3 C20 N4 101.73(19) . . ? N3 C20 C21 129.0(2) . . ? N4 C20 C21 129.3(2) . . ? C22 C21 C26 120.1(2) . . ? C22 C21 C20 119.6(2) . . ? C26 C21 C20 120.3(2) . . ? C21 C22 C23 120.0(2) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C24 C23 C22 119.7(3) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? C25 C24 C23 120.6(2) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C24 C25 C26 120.0(3) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C21 119.6(3) . . ? C25 C26 H26 120.2 . . ? C21 C26 H26 120.2 . . ? N3 C27 C28 108.55(18) . . ? N3 C27 C32 112.4(2) . . ? C28 C27 C32 111.0(2) . . ? N3 C27 H27 108.3 . . ? C28 C27 H27 108.3 . . ? C32 C27 H27 108.3 . . ? C29 C28 C27 110.99(19) . . ? C29 C28 H28A 109.4 . . ? C27 C28 H28A 109.4 . . ? C29 C28 H28B 109.4 . . ? C27 C28 H28B 109.4 . . ? H28A C28 H28B 108.0 . . ? C30 C29 C28 110.3(2) . . ? C30 C29 H29A 109.6 . . ? C28 C29 H29A 109.6 . . ? C30 C29 H29B 109.6 . . ? C28 C29 H29B 109.6 . . ? H29A C29 H29B 108.1 . . ? C29 C30 C31 110.7(2) . . ? C29 C30 H30A 109.5 . . ? C31 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? C31 C30 H30B 109.5 . . ? H30A C30 H30B 108.1 . . ? C32 C31 C30 110.7(2) . . ? C32 C31 H31A 109.5 . . ? C30 C31 H31A 109.5 . . ? C32 C31 H31B 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 108.1 . . ? C31 C32 C27 111.3(2) . . ? C31 C32 H32A 109.4 . . ? C27 C32 H32A 109.4 . . ? C31 C32 H32B 109.4 . . ? C27 C32 H32B 109.4 . . ? H32A C32 H32B 108.0 . . ? N4 C33 C38 108.6(2) . . ? N4 C33 C34 112.1(2) . . ? C38 C33 C34 111.2(2) . . ? N4 C33 H33 108.3 . . ? C38 C33 H33 108.3 . . ? C34 C33 H33 108.3 . . ? C33 C34 C35 111.5(2) . . ? C33 C34 H34A 109.3 . . ? C35 C34 H34A 109.3 . . ? C33 C34 H34B 109.3 . . ? C35 C34 H34B 109.3 . . ? H34A C34 H34B 108.0 . . ? C36 C35 C34 110.4(2) . . ? C36 C35 H35A 109.6 . . ? C34 C35 H35A 109.6 . . ? C36 C35 H35B 109.6 . . ? C34 C35 H35B 109.6 . . ? H35A C35 H35B 108.1 . . ? C37 C36 C35 110.5(2) . . ? C37 C36 H36A 109.6 . . ? C35 C36 H36A 109.6 . . ? C37 C36 H36B 109.6 . . ? C35 C36 H36B 109.6 . . ? H36A C36 H36B 108.1 . . ? C36 C37 C38 111.7(2) . . ? C36 C37 H37A 109.3 . . ? C38 C37 H37A 109.3 . . ? C36 C37 H37B 109.3 . . ? C38 C37 H37B 109.3 . . ? H37A C37 H37B 107.9 . . ? C33 C38 C37 112.0(2) . . ? C33 C38 H38A 109.2 . . ? C37 C38 H38A 109.2 . . ? C33 C38 H38B 109.2 . . ? C37 C38 H38B 109.2 . . ? H38A C38 H38B 107.9 . . ? N1 B1 N2 82.46(17) . . ? N1 B1 Cl2 114.13(19) . . ? N2 B1 Cl2 115.42(19) . . ? N1 B1 Cl1 115.97(19) . . ? N2 B1 Cl1 115.01(18) . . ? Cl2 B1 Cl1 111.24(15) . . ? N3 B2 N4 82.82(16) . . ? N3 B2 Cl4 116.67(18) . . ? N4 B2 Cl4 114.96(18) . . ? N3 B2 Cl3 113.54(18) . . ? N4 B2 Cl3 114.98(18) . . ? Cl4 B2 Cl3 111.30(14) . . ? C1 N1 C8 129.5(2) . . ? C1 N1 B1 88.26(18) . . ? C8 N1 B1 137.7(2) . . ? C1 N2 C14 128.4(2) . . ? C1 N2 B1 87.51(18) . . ? C14 N2 B1 136.6(2) . . ? C20 N3 C27 132.25(19) . . ? C20 N3 B2 87.92(18) . . ? C27 N3 B2 137.48(19) . . ? C20 N4 C33 130.88(19) . . ? C20 N4 B2 87.45(18) . . ? C33 N4 B2 136.01(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 N2 C1 C2 C7 -129.6(3) . . . . ? N1 C1 C2 C7 48.6(4) . . . . ? N2 C1 C2 C3 49.6(4) . . . . ? N1 C1 C2 C3 -132.2(3) . . . . ? C7 C2 C3 C4 -0.2(4) . . . . ? C1 C2 C3 C4 -179.4(2) . . . . ? C2 C3 C4 C5 0.3(4) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? C4 C5 C6 C7 0.0(4) . . . . ? C3 C2 C7 C6 0.1(4) . . . . ? C1 C2 C7 C6 179.3(2) . . . . ? C5 C6 C7 C2 0.0(4) . . . . ? N1 C8 C9 C10 -178.9(2) . . . . ? C13 C8 C9 C10 -55.5(3) . . . . ? C8 C9 C10 C11 57.6(3) . . . . ? C9 C10 C11 C12 -57.0(3) . . . . ? C10 C11 C12 C13 54.9(3) . . . . ? N1 C8 C13 C12 175.8(2) . . . . ? C9 C8 C13 C12 53.9(3) . . . . ? C11 C12 C13 C8 -53.7(3) . . . . ? N2 C14 C15 C16 -176.3(2) . . . . ? C19 C14 C15 C16 -52.6(3) . . . . ? C14 C15 C16 C17 54.7(3) . . . . ? C15 C16 C17 C18 -57.2(3) . . . . ? C16 C17 C18 C19 57.8(3) . . . . ? N2 C14 C19 C18 175.6(2) . . . . ? C15 C14 C19 C18 53.6(3) . . . . ? C17 C18 C19 C14 -56.2(3) . . . . ? N3 C20 C21 C22 40.5(4) . . . . ? N4 C20 C21 C22 -137.8(3) . . . . ? N3 C20 C21 C26 -141.7(3) . . . . ? N4 C20 C21 C26 40.0(4) . . . . ? C26 C21 C22 C23 0.1(4) . . . . ? C20 C21 C22 C23 177.9(2) . . . . ? C21 C22 C23 C24 0.1(4) . . . . ? C22 C23 C24 C25 0.3(4) . . . . ? C23 C24 C25 C26 -0.9(4) . . . . ? C24 C25 C26 C21 1.0(4) . . . . ? C22 C21 C26 C25 -0.6(4) . . . . ? C20 C21 C26 C25 -178.4(2) . . . . ? N3 C27 C28 C29 -179.9(2) . . . . ? C32 C27 C28 C29 -55.9(3) . . . . ? C27 C28 C29 C30 57.4(3) . . . . ? C28 C29 C30 C31 -57.9(3) . . . . ? C29 C30 C31 C32 57.1(3) . . . . ? C30 C31 C32 C27 -55.7(3) . . . . ? N3 C27 C32 C31 176.91(19) . . . . ? C28 C27 C32 C31 55.1(3) . . . . ? N4 C33 C34 C35 175.8(2) . . . . ? C38 C33 C34 C35 54.0(3) . . . . ? C33 C34 C35 C36 -57.0(3) . . . . ? C34 C35 C36 C37 58.0(3) . . . . ? C35 C36 C37 C38 -56.9(3) . . . . ? N4 C33 C38 C37 -176.2(2) . . . . ? C34 C33 C38 C37 -52.4(3) . . . . ? C36 C37 C38 C33 54.3(3) . . . . ? N2 C1 N1 C8 -157.1(2) . . . . ? C2 C1 N1 C8 24.4(4) . . . . ? N2 C1 N1 B1 2.0(2) . . . . ? C2 C1 N1 B1 -176.6(3) . . . . ? C13 C8 N1 C1 70.1(3) . . . . ? C9 C8 N1 C1 -167.0(2) . . . . ? C13 C8 N1 B1 -77.8(3) . . . . ? C9 C8 N1 B1 45.1(4) . . . . ? N2 B1 N1 C1 -1.64(18) . . . . ? Cl2 B1 N1 C1 112.9(2) . . . . ? Cl1 B1 N1 C1 -115.84(19) . . . . ? N2 B1 N1 C8 154.1(3) . . . . ? Cl2 B1 N1 C8 -91.4(3) . . . . ? Cl1 B1 N1 C8 39.9(4) . . . . ? N1 C1 N2 C14 -155.2(2) . . . . ? C2 C1 N2 C14 23.3(4) . . . . ? N1 C1 N2 B1 -1.9(2) . . . . ? C2 C1 N2 B1 176.6(3) . . . . ? C15 C14 N2 C1 -170.3(2) . . . . ? C19 C14 N2 C1 66.2(3) . . . . ? C15 C14 N2 B1 50.5(4) . . . . ? C19 C14 N2 B1 -73.0(3) . . . . ? N1 B1 N2 C1 1.65(18) . . . . ? Cl2 B1 N2 C1 -111.5(2) . . . . ? Cl1 B1 N2 C1 116.8(2) . . . . ? N1 B1 N2 C14 150.8(3) . . . . ? Cl2 B1 N2 C14 37.7(4) . . . . ? Cl1 B1 N2 C14 -94.0(3) . . . . ? N4 C20 N3 C27 -162.0(2) . . . . ? C21 C20 N3 C27 19.3(4) . . . . ? N4 C20 N3 B2 2.4(2) . . . . ? C21 C20 N3 B2 -176.3(2) . . . . ? C28 C27 N3 C20 -175.0(2) . . . . ? C32 C27 N3 C20 61.9(3) . . . . ? C28 C27 N3 B2 28.4(4) . . . . ? C32 C27 N3 B2 -94.7(3) . . . . ? N4 B2 N3 C20 -2.01(17) . . . . ? Cl4 B2 N3 C20 -116.38(19) . . . . ? Cl3 B2 N3 C20 112.15(19) . . . . ? N4 B2 N3 C27 160.9(3) . . . . ? Cl4 B2 N3 C27 46.5(3) . . . . ? Cl3 B2 N3 C27 -85.0(3) . . . . ? N3 C20 N4 C33 -158.4(2) . . . . ? C21 C20 N4 C33 20.3(4) . . . . ? N3 C20 N4 B2 -2.39(19) . . . . ? C21 C20 N4 B2 176.3(2) . . . . ? C38 C33 N4 C20 -172.2(2) . . . . ? C34 C33 N4 C20 64.5(3) . . . . ? C38 C33 N4 B2 43.5(3) . . . . ? C34 C33 N4 B2 -79.7(3) . . . . ? N3 B2 N4 C20 2.01(16) . . . . ? Cl4 B2 N4 C20 118.14(19) . . . . ? Cl3 B2 N4 C20 -110.65(19) . . . . ? N3 B2 N4 C33 155.8(3) . . . . ? Cl4 B2 N4 C33 -88.1(3) . . . . ? Cl3 B2 N4 C33 43.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.359 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.061