# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 1999 # CCDC Number: 440/150 data_global #====================================================================== # 1. SUBMISSION DETAILS _publ_contact_author ; Dr N. C. Norman, School of Chemistry, Cantocks Close, University of Bristol. Bristol. BS8 1TS. ; _publ_contact_author_phone '0117 928 7577' _publ_contact_author_fax '0117 929 0509' _publ_contact_author_email 'N.C.Norman@bris.ac.uk' _publ_requested_journal 'New Journal of Chemistry' _publ_requested_coeditor_name ? _publ_contact_letter ; ; #====================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #====================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; The Platinum Catalysed Diboration of Alkynes Using 1,2- B~2~Cl~2~(NMe~2~)~2~: Formation of 1-Azonia-2-Borata-5-Borole Derivatives ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Anderson, Kirsty M.' ; School of Chemistry University of Bristol Cantocks Close BS8 1TS. Bristol, UK ; 'Lesley, M. J. Gerald' ; School of Chemistry University of Bristol Cantocks Close BS8 1TS. Bristol, UK ; 'Norman, Nicholas C.' ; School of Chemistry University of Bristol Cantocks Close BS8 1TS. Bristol, UK ; 'Orpen, A. Guy' ; School of Chemistry University of Bristol Cantocks Close BS8 1TS. Bristol, UK ; 'Starbuck, Johnathan' ; School of Chemistry University of Bristol Cantocks Close BS8 1TS. Bristol, UK ; #====================================================================== # 4. TEXT # # # N. C. NORMAN # data_3a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H20 B2 Cl2 N2' _chemical_formula_weight 296.83 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.121(3) _cell_length_b 7.1894(6) _cell_length_c 13.5772(17) _cell_angle_alpha 90.00 _cell_angle_beta 95.567(15) _cell_angle_gamma 90.00 _cell_volume 1566.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 42 _cell_measurement_theta_min 5.02 _cell_measurement_theta_max 12.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.401 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 3265 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 3 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2450 _reflns_number_gt 2248 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0365P)^2^+0.8764P] 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 'mixed' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2450 _refine_ls_number_parameters 177 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0887 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.65942(13) 0.2962(3) 0.64126(15) 0.0301(5) Uani 1 1 d . . . B2 B 0.71853(13) 0.5543(3) 0.74059(15) 0.0267(4) Uani 1 1 d . . . Cl1 Cl 0.57320(3) 0.22154(8) 0.54857(4) 0.04614(17) Uani 1 1 d . . . Cl2 Cl 0.68318(3) 0.09558(6) 0.72827(4) 0.04313(16) Uani 1 1 d . . . N1 N 0.63093(9) 0.4715(2) 0.70479(10) 0.0275(3) Uani 1 1 d . . . N2 N 0.73527(10) 0.6479(2) 0.82869(11) 0.0324(4) Uani 1 1 d . . . C1 C 0.58716(12) 0.6141(3) 0.63680(15) 0.0373(5) Uani 1 1 d . . . H1A H 0.5850 0.7305 0.6710 0.056 Uiso 1 1 calc R . . H1B H 0.5315 0.5726 0.6165 0.056 Uiso 1 1 calc R . . H1C H 0.6171 0.6298 0.5796 0.056 Uiso 1 1 calc R . . C2 C 0.57266(12) 0.4155(3) 0.77862(15) 0.0387(5) Uani 1 1 d . . . H2A H 0.5451 0.5238 0.8009 0.058 Uiso 1 1 calc R . . H2B H 0.6035 0.3564 0.8340 0.058 Uiso 1 1 calc R . . H2C H 0.5320 0.3303 0.7484 0.058 Uiso 1 1 calc R . . C3 C 0.67581(14) 0.7157(3) 0.89591(16) 0.0442(5) Uani 1 1 d . . . H3A H 0.6219 0.7302 0.8600 0.066 Uiso 1 1 calc R . . H3B H 0.6944 0.8335 0.9231 0.066 Uiso 1 1 calc R . . H3C H 0.6723 0.6278 0.9485 0.066 Uiso 1 1 calc R . . C4 C 0.82047(14) 0.6988(3) 0.86561(16) 0.0478(6) Uani 1 1 d . . . H4A H 0.8590 0.6390 0.8262 0.072 Uiso 1 1 calc R . . H4B H 0.8314 0.6597 0.9332 0.072 Uiso 1 1 calc R . . H4C H 0.8270 0.8313 0.8617 0.072 Uiso 1 1 calc R . . C5 C 0.77614(13) 0.2844(3) 0.51191(14) 0.0372(5) Uani 1 1 d . . . H5A H 0.8234 0.3554 0.4957 0.056 Uiso 1 1 calc R . . H5B H 0.7339 0.2863 0.4570 0.056 Uiso 1 1 calc R . . H5C H 0.7929 0.1584 0.5261 0.056 Uiso 1 1 calc R . . C6 C 0.74209(11) 0.3676(2) 0.60091(13) 0.0277(4) Uani 1 1 d . . . C7 C 0.77658(10) 0.5068(2) 0.65855(12) 0.0269(4) Uani 1 1 d . . . C8 C 0.85628(11) 0.6019(2) 0.64363(13) 0.0278(4) Uani 1 1 d . . . C9 C 0.85995(12) 0.7950(3) 0.63814(14) 0.0348(4) Uani 1 1 d . . . H9A H 0.8121 0.8647 0.6440 0.042 Uiso 1 1 calc R . . C10 C 0.93352(14) 0.8846(3) 0.62417(16) 0.0455(5) Uani 1 1 d . . . H10A H 0.9346 1.0137 0.6205 0.055 Uiso 1 1 calc R . . C11 C 1.00526(14) 0.7851(3) 0.61556(18) 0.0521(6) Uani 1 1 d . . . H11A H 1.0546 0.8458 0.6053 0.063 Uiso 1 1 calc R . . C12 C 1.00288(14) 0.5957(4) 0.6222(2) 0.0567(6) Uani 1 1 d . . . H12A H 1.0513 0.5273 0.6172 0.068 Uiso 1 1 calc R . . C13 C 0.92956(12) 0.5039(3) 0.63636(17) 0.0436(5) Uani 1 1 d . . . H13A H 0.9294 0.3748 0.6410 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0359(11) 0.0280(10) 0.0263(11) -0.0006(8) 0.0017(9) 0.0004(8) B2 0.0328(10) 0.0213(9) 0.0263(10) 0.0043(8) 0.0037(8) 0.0023(8) Cl1 0.0399(3) 0.0591(3) 0.0384(3) -0.0128(2) -0.0010(2) -0.0090(2) Cl2 0.0572(3) 0.0270(2) 0.0460(3) 0.0076(2) 0.0096(2) 0.0022(2) N1 0.0299(8) 0.0270(7) 0.0262(8) 0.0020(6) 0.0062(6) 0.0008(6) N2 0.0403(9) 0.0312(8) 0.0267(8) -0.0018(7) 0.0088(7) -0.0014(7) C1 0.0350(10) 0.0378(10) 0.0395(11) 0.0073(9) 0.0066(9) 0.0096(8) C2 0.0402(11) 0.0416(11) 0.0368(11) -0.0014(9) 0.0170(9) -0.0060(9) C3 0.0613(14) 0.0394(11) 0.0351(11) -0.0090(9) 0.0203(10) -0.0042(10) C4 0.0497(12) 0.0617(14) 0.0311(11) -0.0063(10) -0.0012(9) -0.0098(11) C5 0.0418(11) 0.0377(10) 0.0331(11) -0.0066(8) 0.0093(8) 0.0016(9) C6 0.0322(9) 0.0265(8) 0.0245(9) 0.0017(7) 0.0034(7) 0.0048(7) C7 0.0292(9) 0.0270(8) 0.0245(9) 0.0033(7) 0.0031(7) 0.0037(7) C8 0.0301(9) 0.0320(9) 0.0217(9) -0.0007(7) 0.0041(7) 0.0003(7) C9 0.0373(10) 0.0324(9) 0.0345(10) 0.0001(8) 0.0033(8) 0.0012(8) C10 0.0538(13) 0.0365(11) 0.0464(12) 0.0004(9) 0.0057(10) -0.0112(10) C11 0.0386(12) 0.0609(15) 0.0585(15) -0.0068(12) 0.0125(10) -0.0179(11) C12 0.0313(11) 0.0626(15) 0.0781(18) -0.0086(13) 0.0141(11) 0.0035(10) C13 0.0349(11) 0.0378(11) 0.0589(13) -0.0019(10) 0.0090(10) 0.0037(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 C6 1.575(3) . ? B1 N1 1.618(3) . ? B1 Cl1 1.861(2) . ? B1 Cl2 1.880(2) . ? B2 N2 1.376(3) . ? B2 C7 1.561(3) . ? B2 N1 1.566(2) . ? N1 C2 1.494(2) . ? N1 C1 1.508(2) . ? N2 C4 1.462(3) . ? N2 C3 1.469(3) . ? C5 C6 1.499(3) . ? C6 C7 1.356(2) . ? C7 C8 1.487(3) . ? C8 C13 1.387(3) . ? C8 C9 1.392(3) . ? C9 C10 1.379(3) . ? C10 C11 1.374(3) . ? C11 C12 1.366(4) . ? C12 C13 1.383(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 C6 B1 N1 103.02(14) . . ? C6 B1 Cl1 117.41(14) . . ? N1 B1 Cl1 110.68(13) . . ? C6 B1 Cl2 109.92(13) . . ? N1 B1 Cl2 108.26(13) . . ? Cl1 B1 Cl2 107.26(10) . . ? N2 B2 C7 130.30(17) . . ? N2 B2 N1 123.41(17) . . ? C7 B2 N1 106.28(14) . . ? C2 N1 C1 107.85(14) . . ? C2 N1 B2 120.07(14) . . ? C1 N1 B2 106.60(13) . . ? C2 N1 B1 112.17(14) . . ? C1 N1 B1 110.06(14) . . ? B2 N1 B1 99.65(13) . . ? B2 N2 C4 121.26(17) . . ? B2 N2 C3 128.12(17) . . ? C4 N2 C3 110.59(16) . . ? C7 C6 C5 126.71(17) . . ? C7 C6 B1 110.67(16) . . ? C5 C6 B1 122.61(16) . . ? C6 C7 C8 124.90(17) . . ? C6 C7 B2 109.45(16) . . ? C8 C7 B2 125.63(16) . . ? C13 C8 C9 117.52(18) . . ? C13 C8 C7 121.96(17) . . ? C9 C8 C7 120.52(17) . . ? C10 C9 C8 120.98(19) . . ? C11 C10 C9 120.7(2) . . ? C12 C11 C10 119.0(2) . . ? C11 C12 C13 121.0(2) . . ? C12 C13 C8 120.8(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 B2 N1 C2 -26.9(2) . . . . ? C7 B2 N1 C2 152.83(15) . . . . ? N2 B2 N1 C1 96.0(2) . . . . ? C7 B2 N1 C1 -84.34(16) . . . . ? N2 B2 N1 B1 -149.61(17) . . . . ? C7 B2 N1 B1 30.10(16) . . . . ? C6 B1 N1 C2 -159.37(14) . . . . ? Cl1 B1 N1 C2 74.32(17) . . . . ? Cl2 B1 N1 C2 -42.98(17) . . . . ? C6 B1 N1 C1 80.56(17) . . . . ? Cl1 B1 N1 C1 -45.76(17) . . . . ? Cl2 B1 N1 C1 -163.05(12) . . . . ? C6 B1 N1 B2 -31.19(15) . . . . ? Cl1 B1 N1 B2 -157.51(12) . . . . ? Cl2 B1 N1 B2 85.20(14) . . . . ? C7 B2 N2 C4 -8.7(3) . . . . ? N1 B2 N2 C4 170.96(17) . . . . ? C7 B2 N2 C3 169.10(18) . . . . ? N1 B2 N2 C3 -11.3(3) . . . . ? N1 B1 C6 C7 22.85(18) . . . . ? Cl1 B1 C6 C7 144.73(14) . . . . ? Cl2 B1 C6 C7 -92.36(16) . . . . ? N1 B1 C6 C5 -158.50(16) . . . . ? Cl1 B1 C6 C5 -36.6(2) . . . . ? Cl2 B1 C6 C5 86.30(18) . . . . ? C5 C6 C7 C8 -0.6(3) . . . . ? B1 C6 C7 C8 177.98(15) . . . . ? C5 C6 C7 B2 177.90(17) . . . . ? B1 C6 C7 B2 -3.52(19) . . . . ? N2 B2 C7 C6 161.53(18) . . . . ? N1 B2 C7 C6 -18.15(18) . . . . ? N2 B2 C7 C8 -20.0(3) . . . . ? N1 B2 C7 C8 160.34(15) . . . . ? C6 C7 C8 C13 -53.4(3) . . . . ? B2 C7 C8 C13 128.3(2) . . . . ? C6 C7 C8 C9 127.7(2) . . . . ? B2 C7 C8 C9 -50.6(2) . . . . ? C13 C8 C9 C10 1.2(3) . . . . ? C7 C8 C9 C10 -179.90(18) . . . . ? C8 C9 C10 C11 -0.2(3) . . . . ? C9 C10 C11 C12 -0.8(4) . . . . ? C10 C11 C12 C13 0.7(4) . . . . ? C11 C12 C13 C8 0.3(4) . . . . ? C9 C8 C13 C12 -1.2(3) . . . . ? C7 C8 C13 C12 179.8(2) . . . . ? C4 C9 C11 C10 -106.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.887 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.887 _refine_diff_density_max 0.224 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.042 #===END data_3c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H26 B2 Cl2 N2' _chemical_formula_weight 386.95 _chemical_melting_point ? _chemical_compound_source ? 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/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 12.410(2) _cell_length_b 12.8779(14) _cell_length_c 13.066(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.428(14) _cell_angle_gamma 90.00 _cell_volume 2088.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 175 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.317 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.760241 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens CCD Area Detector' _diffrn_measurement_method '\w rotation with narrow frame' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 21321 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4779 _reflns_number_gt 3679 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SAINT (Siemens, 1995b)' _computing_data_reduction 'SAINT (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0674P)^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 'mixed' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4779 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_all 0.1095 _refine_ls_wR_factor_ref 0.1055 _refine_ls_goodness_of_fit_all 1.010 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.010 _refine_ls_restrained_S_obs 1.118 _refine_ls_shift/su_max -0.004 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group B1 B 0.24067(14) 0.39843(13) 0.23070(14) 0.0244(4) Uani 1 d . . B2 B 0.32011(15) 0.29106(13) 0.36297(14) 0.0246(4) Uani 1 d . . Cl1 Cl 0.37126(3) 0.43637(3) 0.16654(3) 0.03178(12) Uani 1 d . . Cl2 Cl 0.13760(4) 0.49667(3) 0.19609(4) 0.03703(13) Uani 1 d . . N1 N 0.26228(11) 0.39843(9) 0.35330(10) 0.0245(3) Uani 1 d . . N2 N 0.40102(11) 0.27021(10) 0.43319(10) 0.0288(3) Uani 1 d . . C1 C 0.15695(14) 0.39350(13) 0.41019(14) 0.0351(4) Uani 1 d . . H1A H 0.17137(15) 0.3833(10) 0.4834(2) 0.053 Uiso 1 calc R . H1B H 0.1138(4) 0.3354(6) 0.3841(7) 0.053 Uiso 1 calc R . H1C H 0.1173(5) 0.4586(4) 0.4001(8) 0.053 Uiso 1 calc R . C2 C 0.3219(2) 0.49383(11) 0.38727(14) 0.0331(4) Uani 1 d . . H2A H 0.3159(9) 0.5013(5) 0.4617(2) 0.050 Uiso 1 calc R . H2B H 0.2908(7) 0.5550(2) 0.3536(7) 0.050 Uiso 1 calc R . H2C H 0.3980(3) 0.4875(4) 0.3687(9) 0.050 Uiso 1 calc R . C3 C 0.4262(2) 0.32985(13) 0.52612(13) 0.0371(4) Uani 1 d . . H3A H 0.3634(4) 0.3712(8) 0.5456(6) 0.056 Uiso 1 calc R . H3B H 0.4873(7) 0.3761(7) 0.5130(3) 0.056 Uiso 1 calc R . H3C H 0.4449(10) 0.28203(14) 0.5818(3) 0.056 Uiso 1 calc R . C4 C 0.47923(15) 0.18645(13) 0.41782(15) 0.0363(4) Uani 1 d . . H4A H 0.4649(6) 0.1524(6) 0.3521(5) 0.054 Uiso 1 calc R . H4B H 0.4729(7) 0.1356(5) 0.4732(5) 0.054 Uiso 1 calc R . H4C H 0.5523(2) 0.2154(2) 0.4179(10) 0.054 Uiso 1 calc R . C5 C -0.0780(2) 0.1615(2) -0.1197(2) 0.0683(7) Uani 1 d . . H5A H -0.1396(38) 0.1259(72) -0.0890(12) 0.102 Uiso 0.50 calc PR . H5B H -0.0446(24) 0.1160(66) -0.1706(42) 0.102 Uiso 0.50 calc PR . H5C H -0.1027(63) 0.2255(7) -0.1531(54) 0.102 Uiso 0.50 calc PR . H5D H -0.0517(38) 0.1857(72) -0.1861(12) 0.102 Uiso 0.50 calc PR . H5E H -0.1467(24) 0.1955(66) -0.1045(42) 0.102 Uiso 0.50 calc PR . H5F H -0.0886(63) 0.0861(7) -0.1221(54) 0.102 Uiso 0.50 calc PR . C6 C 0.0035(2) 0.1878(2) -0.03728(14) 0.0407(4) Uani 1 d . . C7 C 0.00960(15) 0.12989(14) 0.05272(14) 0.0366(4) Uani 1 d . . H7A H -0.03595(15) 0.07122(14) 0.06084(14) 0.044 Uiso 1 calc R . C8 C 0.08100(14) 0.15641(13) 0.13064(13) 0.0298(4) Uani 1 d . . H8A H 0.08387(14) 0.11544(13) 0.19107(13) 0.036 Uiso 1 calc R . C9 C 0.14884(13) 0.24262(12) 0.12147(12) 0.0258(3) Uani 1 d . . C10 C 0.14271(14) 0.29985(13) 0.03076(13) 0.0323(4) Uani 1 d . . H10A H 0.18798(14) 0.35869(13) 0.02248(13) 0.039 Uiso 1 calc R . C11 C 0.0719(2) 0.27266(15) -0.04758(14) 0.0383(4) Uani 1 d . . H11A H 0.0702(2) 0.31240(15) -0.10883(14) 0.046 Uiso 1 calc R . C12 C 0.21747(12) 0.27836(11) 0.20772(12) 0.0240(3) Uani 1 d . . C13 C 0.26988(12) 0.21928(11) 0.27879(12) 0.0246(3) Uani 1 d . . C14 C 0.27947(13) 0.10379(11) 0.28134(12) 0.0247(3) Uani 1 d . . C15 C 0.26092(14) 0.04927(12) 0.37206(13) 0.0300(4) Uani 1 d . . H15A H 0.23911(14) 0.08628(12) 0.43129(13) 0.036 Uiso 1 calc R . C16 C 0.27366(15) -0.05801(12) 0.37760(13) 0.0323(4) Uani 1 d . . H16A H 0.25840(15) -0.09310(12) 0.43979(13) 0.039 Uiso 1 calc R . C17 C 0.30838(14) -0.11441(12) 0.29345(13) 0.0297(4) Uani 1 d . . C18 C 0.32801(14) -0.06017(12) 0.20296(13) 0.0300(4) Uani 1 d . . H18A H 0.35271(14) -0.09697(12) 0.14465(13) 0.036 Uiso 1 calc R . C19 C 0.31221(13) 0.04642(12) 0.19631(13) 0.0276(3) Uani 1 d . . H19A H 0.32383(13) 0.08081(12) 0.13302(13) 0.033 Uiso 1 calc R . C20 C 0.3247(2) -0.23069(13) 0.2998(2) 0.0415(4) Uani 1 d . . H20A H 0.3424(45) -0.2578(6) 0.2318(9) 0.062 Uiso 0.50 calc PR . H20B H 0.2584(15) -0.2636(4) 0.3240(42) 0.062 Uiso 0.50 calc PR . H20C H 0.3838(30) -0.2460(2) 0.3475(33) 0.062 Uiso 0.50 calc PR . H20E H 0.3140(45) -0.2538(6) 0.3704(9) 0.062 Uiso 0.50 calc PR . H20E H 0.3980(15) -0.2480(4) 0.2782(42) 0.062 Uiso 0.50 calc PR . H20F H 0.2726(30) -0.2656(2) 0.2547(33) 0.062 Uiso 0.50 calc PR . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0275(9) 0.0187(8) 0.0270(9) 0.0021(7) -0.0023(7) -0.0016(7) B2 0.0322(10) 0.0166(8) 0.0250(9) 0.0001(6) 0.0014(7) -0.0012(7) Cl1 0.0344(2) 0.0296(2) 0.0314(2) 0.0051(2) 0.0006(2) -0.0077(2) Cl2 0.0399(3) 0.0271(2) 0.0440(3) 0.0016(2) -0.0104(2) 0.0082(2) N1 0.0324(7) 0.0152(6) 0.0260(7) -0.0021(5) -0.0015(6) -0.0010(5) N2 0.0347(8) 0.0223(7) 0.0292(7) -0.0038(5) -0.0035(6) 0.0013(6) C1 0.0393(10) 0.0311(9) 0.0350(9) -0.0029(7) 0.0086(8) 0.0015(7) C2 0.0483(11) 0.0161(7) 0.0348(9) -0.0040(6) -0.0084(8) -0.0034(7) C3 0.0515(11) 0.0312(9) 0.0285(9) -0.0034(7) -0.0114(8) 0.0000(8) C4 0.0359(10) 0.0283(9) 0.0447(11) -0.0016(7) -0.0048(8) 0.0056(7) C5 0.072(2) 0.087(2) 0.0455(13) -0.0013(12) -0.0236(12) -0.0318(14) C6 0.0393(10) 0.0513(11) 0.0315(9) -0.0091(8) -0.0061(8) -0.0098(8) C7 0.0379(10) 0.0355(9) 0.0365(10) -0.0070(7) -0.0009(8) -0.0134(8) C8 0.0338(9) 0.0273(8) 0.0283(8) -0.0021(6) 0.0007(7) -0.0052(7) C9 0.0289(8) 0.0224(7) 0.0260(8) -0.0036(6) 0.0000(7) -0.0018(6) C10 0.0358(9) 0.0313(9) 0.0297(9) 0.0003(7) -0.0007(7) -0.0084(7) C11 0.0441(11) 0.0452(10) 0.0255(9) 0.0031(8) -0.0047(8) -0.0060(8) C12 0.0272(8) 0.0199(7) 0.0248(8) -0.0015(6) 0.0014(6) -0.0043(6) C13 0.0305(8) 0.0166(7) 0.0267(8) -0.0007(6) 0.0002(7) -0.0028(6) C14 0.0296(8) 0.0170(7) 0.0276(8) -0.0013(6) -0.0017(7) -0.0034(6) C15 0.0419(10) 0.0225(8) 0.0257(8) -0.0018(6) 0.0019(7) -0.0008(7) C16 0.0437(10) 0.0223(8) 0.0309(9) 0.0047(6) 0.0008(8) -0.0027(7) C17 0.0345(9) 0.0185(7) 0.0361(9) 0.0004(6) -0.0022(7) -0.0014(6) C18 0.0357(9) 0.0219(8) 0.0324(9) -0.0051(6) 0.0046(7) -0.0020(6) C19 0.0343(9) 0.0219(8) 0.0265(8) 0.0006(6) 0.0013(7) -0.0052(6) C20 0.0567(12) 0.0195(8) 0.0483(11) 0.0019(7) 0.0019(9) 0.0034(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 C12 1.601(2) . ? B1 N1 1.622(2) . ? B1 Cl2 1.853(2) . ? B1 Cl1 1.894(2) . ? B2 N2 1.381(2) . ? B2 N1 1.563(2) . ? B2 C13 1.563(2) . ? N1 C2 1.500(2) . ? N1 C1 1.510(2) . ? N2 C4 1.466(2) . ? N2 C3 1.469(2) . ? C5 C6 1.511(3) . ? C6 C11 1.391(3) . ? C6 C7 1.394(3) . ? C7 C8 1.387(2) . ? C8 C9 1.399(2) . ? C9 C10 1.397(2) . ? C9 C12 1.481(2) . ? C10 C11 1.389(2) . ? C12 C13 1.362(2) . ? C13 C14 1.492(2) . ? C14 C19 1.397(2) . ? C14 C15 1.398(2) . ? C15 C16 1.392(2) . ? C16 C17 1.389(2) . ? C17 C18 1.396(2) . ? C17 C20 1.513(2) . ? C18 C19 1.389(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 C12 B1 N1 102.32(12) . . ? C12 B1 Cl2 119.40(12) . . ? N1 B1 Cl2 110.47(11) . . ? C12 B1 Cl1 108.63(11) . . ? N1 B1 Cl1 107.54(11) . . ? Cl2 B1 Cl1 107.89(9) . . ? N2 B2 N1 123.84(14) . . ? N2 B2 C13 129.54(14) . . ? N1 B2 C13 106.61(13) . . ? C2 N1 C1 108.41(13) . . ? C2 N1 B2 118.40(13) . . ? C1 N1 B2 108.77(12) . . ? C2 N1 B1 111.71(12) . . ? C1 N1 B1 110.42(13) . . ? B2 N1 B1 98.76(11) . . ? B2 N2 C4 122.06(14) . . ? B2 N2 C3 126.65(14) . . ? C4 N2 C3 111.15(14) . . ? C11 C6 C7 118.2(2) . . ? C11 C6 C5 120.9(2) . . ? C7 C6 C5 120.9(2) . . ? C8 C7 C6 121.2(2) . . ? C7 C8 C9 120.9(2) . . ? C10 C9 C8 117.53(15) . . ? C10 C9 C12 120.59(14) . . ? C8 C9 C12 121.64(14) . . ? C11 C10 C9 121.5(2) . . ? C10 C11 C6 120.7(2) . . ? C13 C12 C9 127.90(14) . . ? C13 C12 B1 109.11(13) . . ? C9 C12 B1 123.00(13) . . ? C12 C13 C14 127.55(14) . . ? C12 C13 B2 109.60(13) . . ? C14 C13 B2 122.85(13) . . ? C19 C14 C15 117.34(14) . . ? C19 C14 C13 122.20(14) . . ? C15 C14 C13 120.39(14) . . ? C16 C15 C14 121.54(15) . . ? C17 C16 C15 120.9(2) . . ? C16 C17 C18 117.77(14) . . ? C16 C17 C20 121.1(2) . . ? C18 C17 C20 121.1(2) . . ? C19 C18 C17 121.45(15) . . ? C18 C19 C14 120.97(15) . . ? 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 B2 N1 C2 26.0(2) . . . . ? C13 B2 N1 C2 -152.87(14) . . . . ? N2 B2 N1 C1 -98.3(2) . . . . ? C13 B2 N1 C1 82.9(2) . . . . ? N2 B2 N1 B1 146.6(2) . . . . ? C13 B2 N1 B1 -32.29(15) . . . . ? C12 B1 N1 C2 160.48(13) . . . . ? Cl2 B1 N1 C2 -71.36(15) . . . . ? Cl1 B1 N1 C2 46.15(15) . . . . ? C12 B1 N1 C1 -78.80(14) . . . . ? Cl2 B1 N1 C1 49.36(14) . . . . ? Cl1 B1 N1 C1 166.87(10) . . . . ? C12 B1 N1 B2 35.08(14) . . . . ? Cl2 B1 N1 B2 163.24(11) . . . . ? Cl1 B1 N1 B2 -79.25(12) . . . . ? N1 B2 N2 C4 -157.1(2) . . . . ? C13 B2 N2 C4 21.4(3) . . . . ? N1 B2 N2 C3 18.1(3) . . . . ? C13 B2 N2 C3 -163.3(2) . . . . ? C11 C6 C7 C8 0.7(3) . . . . ? C5 C6 C7 C8 -177.1(2) . . . . ? C6 C7 C8 C9 0.3(3) . . . . ? C7 C8 C9 C10 -0.7(2) . . . . ? C7 C8 C9 C12 173.7(2) . . . . ? C8 C9 C10 C11 0.1(3) . . . . ? C12 C9 C10 C11 -174.4(2) . . . . ? C9 C10 C11 C6 0.9(3) . . . . ? C7 C6 C11 C10 -1.3(3) . . . . ? C5 C6 C11 C10 176.5(2) . . . . ? C10 C9 C12 C13 -149.1(2) . . . . ? C8 C9 C12 C13 36.6(2) . . . . ? C10 C9 C12 B1 31.0(2) . . . . ? C8 C9 C12 B1 -143.3(2) . . . . ? N1 B1 C12 C13 -27.7(2) . . . . ? Cl2 B1 C12 C13 -149.93(13) . . . . ? Cl1 B1 C12 C13 85.87(14) . . . . ? N1 B1 C12 C9 152.25(14) . . . . ? Cl2 B1 C12 C9 30.0(2) . . . . ? Cl1 B1 C12 C9 -94.2(2) . . . . ? C9 C12 C13 C14 6.3(3) . . . . ? B1 C12 C13 C14 -173.77(15) . . . . ? C9 C12 C13 B2 -172.8(2) . . . . ? B1 C12 C13 B2 7.1(2) . . . . ? N2 B2 C13 C12 -161.5(2) . . . . ? N1 B2 C13 C12 17.3(2) . . . . ? N2 B2 C13 C14 19.4(3) . . . . ? N1 B2 C13 C14 -161.88(13) . . . . ? C12 C13 C14 C19 50.0(2) . . . . ? B2 C13 C14 C19 -131.0(2) . . . . ? C12 C13 C14 C15 -133.3(2) . . . . ? B2 C13 C14 C15 45.7(2) . . . . ? C19 C14 C15 C16 -0.5(2) . . . . ? C13 C14 C15 C16 -177.3(2) . . . . ? C14 C15 C16 C17 1.8(3) . . . . ? C15 C16 C17 C18 -1.2(3) . . . . ? C15 C16 C17 C20 178.7(2) . . . . ? C16 C17 C18 C19 -0.8(3) . . . . ? C20 C17 C18 C19 179.4(2) . . . . ? C17 C18 C19 C14 2.2(3) . . . . ? C15 C14 C19 C18 -1.5(2) . . . . ? C13 C14 C19 C18 175.26(15) . . . . ? _refine_diff_density_max 1.086 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.050 #===END data_3d _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H26 B2 Cl2 N2 O2' _chemical_formula_weight 418.95 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 10.870(3) _cell_length_b 12.404(2) _cell_length_c 16.086(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.185(9) _cell_angle_gamma 90.00 _cell_volume 2167.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 115 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.317 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.858247 _exptl_absorpt_correction_T_max 1.000000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens CCD Area Detector' _diffrn_measurement_method '\w rotation with narrow frame' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 13263 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0643 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4946 _reflns_number_gt 3194 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SAINT (Siemens, 1995b)' _computing_data_reduction 'SAINT (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0445P)^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 'mixed' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4946 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0900 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_all 0.1045 _refine_ls_wR_factor_ref 0.0897 _refine_ls_goodness_of_fit_all 0.998 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 0.998 _refine_ls_restrained_S_obs 1.080 _refine_ls_shift/su_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group B1 B 0.8811(2) 0.3031(2) 0.15557(14) 0.0276(5) Uani 1 d . . B2 B 0.9210(2) 0.4911(2) 0.19182(14) 0.0261(5) Uani 1 d . . Cl1 Cl 0.97047(5) 0.28317(5) 0.05872(3) 0.0374(2) Uani 1 d . . Cl2 Cl 0.76286(5) 0.19554(4) 0.15855(4) 0.0387(2) Uani 1 d . . N1 N 0.8159(2) 0.42105(13) 0.15112(10) 0.0277(4) Uani 1 d . . N2 N 0.9400(2) 0.59727(13) 0.17057(10) 0.0303(4) Uani 1 d . . O1 O 1.12584(14) -0.06033(11) 0.41364(9) 0.0353(4) Uani 1 d . . O2 O 1.25246(14) 0.58334(13) 0.54026(9) 0.0401(4) Uani 1 d . . C1 C 0.7100(2) 0.4271(2) 0.20907(14) 0.0380(6) Uani 1 d . . H1A H 0.6837(8) 0.5023(2) 0.2145(7) 0.057 Uiso 1 calc R . H1B H 0.7364(4) 0.3991(10) 0.2639(3) 0.057 Uiso 1 calc R . H1C H 0.6411(5) 0.3838(9) 0.1864(4) 0.057 Uiso 1 calc R . C2 C 0.7669(2) 0.4471(2) 0.06466(14) 0.0421(6) Uani 1 d . . H2A H 0.7054(10) 0.5047(9) 0.0674(2) 0.063 Uiso 1 calc R . H2B H 0.7287(13) 0.3827(4) 0.0397(4) 0.063 Uiso 1 calc R . H2C H 0.8347(3) 0.4710(12) 0.0307(3) 0.063 Uiso 1 calc R . C3 C 0.8510(2) 0.6701(2) 0.12917(14) 0.0404(6) Uani 1 d . . H3A H 0.7691(3) 0.6369(5) 0.1280(8) 0.061 Uiso 1 calc R . H3B H 0.8755(8) 0.6837(10) 0.0721(3) 0.061 Uiso 1 calc R . H3C H 0.8488(10) 0.7384(5) 0.1597(5) 0.061 Uiso 1 calc R . C4 C 1.0557(2) 0.6530(2) 0.1920(2) 0.0445(6) Uani 1 d . . H4A H 1.1151(5) 0.6015(3) 0.2164(9) 0.067 Uiso 1 calc R . H4B H 1.0406(3) 0.7103(8) 0.2323(7) 0.067 Uiso 1 calc R . H4C H 1.0889(7) 0.6845(10) 0.1417(2) 0.067 Uiso 1 calc R . C5 C 1.2042(2) -0.1382(2) 0.3776(2) 0.0459(6) Uani 1 d . . H5A H 1.2255(12) -0.1940(7) 0.4189(3) 0.069 Uiso 1 calc R . H5B H 1.2794(7) -0.1028(3) 0.3599(9) 0.069 Uiso 1 calc R . H5C H 1.1614(6) -0.1713(9) 0.3294(6) 0.069 Uiso 1 calc R . C6 C 1.0931(2) 0.0285(2) 0.36639(12) 0.0261(5) Uani 1 d . . C7 C 1.0304(2) 0.1088(2) 0.40757(13) 0.0274(5) Uani 1 d . . H7A H 1.0132(2) 0.1003(2) 0.46467(13) 0.033 Uiso 1 calc R . C8 C 0.9928(2) 0.2010(2) 0.36551(12) 0.0263(5) Uani 1 d . . H8A H 0.9508(2) 0.2558(2) 0.39436(12) 0.032 Uiso 1 calc R . C9 C 1.0157(2) 0.2150(2) 0.28133(12) 0.0237(4) Uani 1 d . . C10 C 1.0762(2) 0.1325(2) 0.24088(13) 0.0304(5) Uani 1 d . . H10A H 1.0906(2) 0.1393(2) 0.18323(13) 0.037 Uiso 1 calc R . C11 C 1.1161(2) 0.0403(2) 0.28315(13) 0.0302(5) Uani 1 d . . H11A H 1.1590(2) -0.0144(2) 0.25476(13) 0.036 Uiso 1 calc R . C12 C 0.9704(2) 0.3122(2) 0.23536(12) 0.0235(4) Uani 1 d . . C13 C 0.9931(2) 0.4165(2) 0.25565(12) 0.0251(5) Uani 1 d . . C14 C 1.0672(2) 0.4562(2) 0.32949(12) 0.0252(5) Uani 1 d . . C15 C 1.0241(2) 0.5445(2) 0.37377(13) 0.0329(5) Uani 1 d . . H15A H 0.9492(2) 0.5780(2) 0.35549(13) 0.040 Uiso 1 calc R . C16 C 1.0866(2) 0.5843(2) 0.44300(13) 0.0355(5) Uani 1 d . . H16A H 1.0541(2) 0.6437(2) 0.47226(13) 0.043 Uiso 1 calc R . C17 C 1.1971(2) 0.5380(2) 0.47035(13) 0.0301(5) Uani 1 d . . C18 C 1.2422(2) 0.4502(2) 0.42787(13) 0.0291(5) Uani 1 d . . H18A H 1.3173(2) 0.4173(2) 0.44616(13) 0.035 Uiso 1 calc R . C19 C 1.1770(2) 0.4102(2) 0.35829(12) 0.0267(5) Uani 1 d . . H19A H 1.2087(2) 0.3498(2) 0.32979(12) 0.032 Uiso 1 calc R . C20 C 1.3752(2) 0.5502(2) 0.56075(14) 0.0379(6) Uani 1 d . . H20A H 1.4054(5) 0.5882(8) 0.6109(5) 0.057 Uiso 1 calc R . H20B H 1.4280(3) 0.5672(10) 0.5145(4) 0.057 Uiso 1 calc R . H20C H 1.3767(3) 0.4723(3) 0.5710(9) 0.057 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0282(13) 0.0287(13) 0.0260(13) -0.0004(10) 0.0030(10) -0.0017(11) B2 0.0239(13) 0.0302(13) 0.0246(12) -0.0014(10) 0.0044(10) 0.0039(10) Cl1 0.0385(3) 0.0481(4) 0.0257(3) -0.0031(3) 0.0037(2) 0.0030(3) Cl2 0.0331(3) 0.0349(3) 0.0478(4) -0.0032(3) -0.0005(2) -0.0084(3) N1 0.0252(10) 0.0309(10) 0.0269(9) 0.0026(8) -0.0020(7) 0.0026(8) N2 0.0332(11) 0.0278(10) 0.0299(10) 0.0051(8) 0.0004(8) 0.0010(8) O1 0.0415(10) 0.0298(8) 0.0344(9) 0.0069(7) 0.0006(7) 0.0080(7) O2 0.0350(10) 0.0480(10) 0.0368(9) -0.0179(7) -0.0057(7) 0.0030(8) C1 0.0266(13) 0.0383(14) 0.0495(15) -0.0012(11) 0.0069(10) 0.0024(10) C2 0.0421(15) 0.0451(14) 0.0378(13) 0.0028(11) -0.0144(11) 0.0060(12) C3 0.046(2) 0.0337(13) 0.0417(14) 0.0100(10) 0.0038(11) 0.0088(11) C4 0.051(2) 0.0340(13) 0.049(2) 0.0062(11) -0.0023(12) -0.0103(12) C5 0.052(2) 0.0359(13) 0.050(2) 0.0084(12) 0.0004(12) 0.0134(12) C6 0.0228(12) 0.0277(11) 0.0275(11) 0.0030(9) -0.0026(9) -0.0017(9) C7 0.0294(12) 0.0315(12) 0.0212(10) 0.0025(9) 0.0007(9) -0.0028(9) C8 0.0274(12) 0.0272(11) 0.0244(11) -0.0028(9) 0.0013(8) -0.0003(9) C9 0.0225(11) 0.0231(11) 0.0254(11) -0.0008(8) -0.0001(8) -0.0004(8) C10 0.0335(13) 0.0339(12) 0.0240(11) 0.0020(9) 0.0026(9) 0.0035(10) C11 0.0324(13) 0.0288(12) 0.0296(12) -0.0029(9) 0.0031(9) 0.0074(10) C12 0.0224(11) 0.0263(11) 0.0220(10) 0.0016(8) 0.0045(8) 0.0000(8) C13 0.0249(11) 0.0274(11) 0.0231(11) 0.0006(9) 0.0032(8) 0.0009(9) C14 0.0268(12) 0.0227(11) 0.0263(11) 0.0012(9) 0.0031(9) -0.0009(9) C15 0.0321(13) 0.0338(12) 0.0326(12) -0.0026(10) -0.0025(10) 0.0079(10) C16 0.0381(14) 0.0326(12) 0.0359(13) -0.0096(10) 0.0023(10) 0.0049(10) C17 0.0306(13) 0.0320(12) 0.0276(12) -0.0046(9) 0.0007(9) -0.0033(10) C18 0.0256(12) 0.0308(12) 0.0308(12) -0.0006(9) -0.0003(9) 0.0024(9) C19 0.0273(12) 0.0229(11) 0.0300(12) -0.0025(9) 0.0023(9) 0.0003(9) C20 0.0387(14) 0.0382(13) 0.0362(13) -0.0067(10) -0.0078(10) -0.0021(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 C12 1.584(3) . ? B1 N1 1.626(3) . ? B1 Cl2 1.854(2) . ? B1 Cl1 1.884(2) . ? B2 N2 1.378(3) . ? B2 N1 1.559(3) . ? B2 C13 1.569(3) . ? N1 C2 1.505(3) . ? N1 C1 1.511(3) . ? N2 C3 1.465(3) . ? N2 C4 1.465(3) . ? O1 C6 1.378(2) . ? O1 C5 1.425(3) . ? O2 C17 1.375(2) . ? O2 C20 1.423(3) . ? C6 C11 1.379(3) . ? C6 C7 1.389(3) . ? C7 C8 1.383(3) . ? C8 C9 1.397(3) . ? C9 C10 1.391(3) . ? C9 C12 1.489(3) . ? C10 C11 1.392(3) . ? C12 C13 1.354(3) . ? C13 C14 1.493(3) . ? C14 C19 1.387(3) . ? C14 C15 1.397(3) . ? C15 C16 1.374(3) . ? C16 C17 1.388(3) . ? C17 C18 1.385(3) . ? C18 C19 1.393(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 C12 B1 N1 102.9(2) . . ? C12 B1 Cl2 115.77(15) . . ? N1 B1 Cl2 110.33(15) . . ? C12 B1 Cl1 111.1(2) . . ? N1 B1 Cl1 108.61(14) . . ? Cl2 B1 Cl1 107.87(12) . . ? N2 B2 N1 122.9(2) . . ? N2 B2 C13 130.5(2) . . ? N1 B2 C13 106.6(2) . . ? C2 N1 C1 107.9(2) . . ? C2 N1 B2 119.7(2) . . ? C1 N1 B2 106.1(2) . . ? C2 N1 B1 111.9(2) . . ? C1 N1 B1 111.0(2) . . ? B2 N1 B1 99.9(2) . . ? B2 N2 C3 126.8(2) . . ? B2 N2 C4 121.9(2) . . ? C3 N2 C4 111.3(2) . . ? C6 O1 C5 117.6(2) . . ? C17 O2 C20 116.6(2) . . ? O1 C6 C11 124.6(2) . . ? O1 C6 C7 115.6(2) . . ? C11 C6 C7 119.8(2) . . ? C8 C7 C6 120.1(2) . . ? C7 C8 C9 121.1(2) . . ? C10 C9 C8 117.9(2) . . ? C10 C9 C12 121.1(2) . . ? C8 C9 C12 121.0(2) . . ? C9 C10 C11 121.3(2) . . ? C6 C11 C10 119.8(2) . . ? C13 C12 C9 126.9(2) . . ? C13 C12 B1 111.3(2) . . ? C9 C12 B1 121.7(2) . . ? C12 C13 C14 126.5(2) . . ? C12 C13 B2 108.9(2) . . ? C14 C13 B2 124.5(2) . . ? C19 C14 C15 117.0(2) . . ? C19 C14 C13 124.2(2) . . ? C15 C14 C13 118.9(2) . . ? C16 C15 C14 122.0(2) . . ? C15 C16 C17 120.3(2) . . ? O2 C17 C18 125.0(2) . . ? O2 C17 C16 115.9(2) . . ? C18 C17 C16 119.1(2) . . ? C17 C18 C19 119.9(2) . . ? C14 C19 C18 121.8(2) . . ? _refine_diff_density_max 0.250 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.053 #===END data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H27 B2 Cl3 N2' _chemical_formula_weight 423.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 20.496(9) _cell_length_b 9.775(4) _cell_length_c 23.894(13) _cell_angle_alpha 90.00 _cell_angle_beta 114.37(6) _cell_angle_gamma 90.00 _cell_volume 4360(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 65 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1776 _exptl_absorpt_coefficient_mu 0.428 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6917 _exptl_absorpt_correction_T_max 0.9077 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 22153 _diffrn_reflns_av_R_equivalents 0.0857 _diffrn_reflns_av_sigmaI/netI 0.1075 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7670 _reflns_number_gt 4398 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SAINT (Siemens, 1995b)' _computing_data_reduction 'SAINT (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _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^)+(0.0484P)^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 ; Hydrogen atoms H98 and H99 were located in the electron density difference map and refined using isotropic displacement parameters without positional constraints. All other hydrogen atoms were constrained to ideal geometries and refined using isotropic displacement parameters. ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7670 _refine_ls_number_parameters 507 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1246 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1262 _refine_ls_wR_factor_gt 0.1020 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.3052(2) 0.7378(5) 0.0582(2) 0.0251(11) Uani 1 1 d . . . B2 B 0.1856(2) 0.7932(5) 0.0551(2) 0.0252(11) Uani 1 1 d . . . N1 N 0.23206(17) 0.8143(3) 0.01580(14) 0.0253(8) Uani 1 1 d . . . N2 N 0.2060(2) 0.9047(3) 0.10966(16) 0.0276(8) Uani 1 1 d . . . H98 H 0.253(2) 0.910(4) 0.1261(18) 0.037(13) Uiso 1 1 d . . . Cl1 Cl 0.35594(6) 0.68266(11) 0.01298(5) 0.0364(3) Uani 1 1 d . . . Cl2 Cl 0.36518(5) 0.86298(10) 0.11858(5) 0.0331(3) Uani 1 1 d . . . Cl3 Cl 0.08812(5) 0.82143(10) 0.00745(5) 0.0306(3) Uani 1 1 d . . . C1 C 0.1952(2) 0.7384(4) -0.04416(18) 0.0343(11) Uani 1 1 d . . . H1A H 0.1490 0.7816 -0.0685 0.051 Uiso 1 1 calc R . . H1B H 0.1875 0.6430 -0.0358 0.051 Uiso 1 1 calc R . . H1C H 0.2253 0.7412 -0.0671 0.051 Uiso 1 1 calc R . . C2 C 0.2428(2) 0.9570(4) -0.0020(2) 0.0378(12) Uani 1 1 d . . . H2A H 0.1961 0.9983 -0.0268 0.057 Uiso 1 1 calc R . . H2B H 0.2717 0.9541 -0.0259 0.057 Uiso 1 1 calc R . . H2C H 0.2675 1.0118 0.0352 0.057 Uiso 1 1 calc R . . C3 C 0.1761(2) 1.0464(4) 0.0945(2) 0.0411(12) Uani 1 1 d . . . H3A H 0.2014 1.1070 0.1295 0.062 Uiso 1 1 calc R . . H3B H 0.1250 1.0450 0.0858 0.062 Uiso 1 1 calc R . . H3C H 0.1824 1.0799 0.0584 0.062 Uiso 1 1 calc R . . C4 C 0.1884(2) 0.8530(4) 0.16088(19) 0.0369(11) Uani 1 1 d . . . H4A H 0.1948 0.9269 0.1904 0.055 Uiso 1 1 calc R . . H4B H 0.2204 0.7769 0.1816 0.055 Uiso 1 1 calc R . . H4C H 0.1386 0.8213 0.1441 0.055 Uiso 1 1 calc R . . C5 C 0.4731(2) 0.1588(4) 0.1874(2) 0.0379(11) Uani 1 1 d . . . H5A H 0.5217 0.1934 0.1986 0.057 Uiso 0.50 1 calc PR . . H5B H 0.4618 0.0903 0.1548 0.057 Uiso 0.50 1 calc PR . . H5C H 0.4700 0.1168 0.2235 0.057 Uiso 0.50 1 calc PR . . H5D H 0.4473 0.0736 0.1860 0.057 Uiso 0.50 1 calc PR . . H5E H 0.5072 0.1767 0.2298 0.057 Uiso 0.50 1 calc PR . . H5F H 0.4990 0.1502 0.1611 0.057 Uiso 0.50 1 calc PR . . C6 C 0.4207(2) 0.2750(4) 0.16501(18) 0.0239(9) Uani 1 1 d . . . C7 C 0.3485(2) 0.2544(4) 0.12836(18) 0.0270(10) Uani 1 1 d . . . H7A H 0.3311 0.1634 0.1193 0.032 Uiso 1 1 calc R . . C8 C 0.3010(2) 0.3614(4) 0.10464(17) 0.0255(10) Uani 1 1 d . . . H8A H 0.2519 0.3427 0.0799 0.031 Uiso 1 1 calc R . . C9 C 0.3245(2) 0.4971(4) 0.11685(17) 0.0229(9) Uani 1 1 d . . . C10 C 0.3965(2) 0.5170(4) 0.15474(19) 0.0310(10) Uani 1 1 d . . . H10 H 0.4139 0.6079 0.1646 0.037 Uiso 1 1 calc R . . C11 C 0.4436(2) 0.4101(4) 0.17845(19) 0.0327(11) Uani 1 1 d . . . H11A H 0.4924 0.4286 0.2043 0.039 Uiso 1 1 calc R . . C12 C 0.2782(2) 0.6178(4) 0.08866(17) 0.0233(9) Uani 1 1 d . . . C13 C 0.2113(2) 0.6427(4) 0.08411(17) 0.0229(9) Uani 1 1 d . . . C14 C 0.1702(2) 0.5475(4) 0.10629(18) 0.0213(9) Uani 1 1 d . . . C15 C 0.1021(2) 0.5040(4) 0.06733(19) 0.0286(10) Uani 1 1 d . . . H15A H 0.0810 0.5385 0.0266 0.034 Uiso 1 1 calc R . . C16 C 0.0644(2) 0.4120(4) 0.0862(2) 0.0343(11) Uani 1 1 d . . . H16A H 0.0188 0.3814 0.0575 0.041 Uiso 1 1 calc R . . C17 C 0.0912(2) 0.3628(4) 0.1459(2) 0.0307(10) Uani 1 1 d . . . C18 C 0.1588(2) 0.4058(4) 0.18489(19) 0.0315(11) Uani 1 1 d . . . H18A H 0.1792 0.3729 0.2259 0.038 Uiso 1 1 calc R . . C19 C 0.1979(2) 0.4959(4) 0.16590(18) 0.0279(10) Uani 1 1 d . . . H19A H 0.2445 0.5229 0.1941 0.033 Uiso 1 1 calc R . . C20 C 0.0484(3) 0.2657(5) 0.1675(2) 0.0545(15) Uani 1 1 d . . . H20A H 0.0122 0.2190 0.1320 0.082 Uiso 0.50 1 calc PR . . H20B H 0.0248 0.3176 0.1889 0.082 Uiso 0.50 1 calc PR . . H20C H 0.0807 0.1979 0.1955 0.082 Uiso 0.50 1 calc PR . . H20D H 0.0662 0.2707 0.2123 0.082 Uiso 0.50 1 calc PR . . H20E H 0.0537 0.1721 0.1554 0.082 Uiso 0.50 1 calc PR . . H20F H -0.0022 0.2918 0.1487 0.082 Uiso 0.50 1 calc PR . . B3 B 0.3591(3) 0.4361(5) -0.1652(2) 0.0286(12) Uani 1 1 d . . . B4 B 0.3576(3) 0.2274(5) -0.1062(2) 0.0274(12) Uani 1 1 d . . . N3 N 0.38452(16) 0.2770(3) -0.15758(15) 0.0268(8) Uani 1 1 d . . . N4 N 0.41752(18) 0.2683(4) -0.03886(16) 0.0286(9) Uani 1 1 d . . . H99 H 0.4374(19) 0.347(4) -0.0461(17) 0.028(12) Uiso 1 1 d . . . Cl4 Cl 0.35234(6) 0.50744(12) -0.23987(5) 0.0396(3) Uani 1 1 d . . . Cl5 Cl 0.43112(6) 0.54206(11) -0.10299(5) 0.0350(3) Uani 1 1 d . . . Cl6 Cl 0.34802(6) 0.03772(10) -0.10519(5) 0.0370(3) Uani 1 1 d . . . C21 C 0.3419(2) 0.2034(4) -0.21699(19) 0.0375(11) Uani 1 1 d . . . H21A H 0.3531 0.1055 -0.2119 0.056 Uiso 1 1 calc R . . H21B H 0.3542 0.2403 -0.2496 0.056 Uiso 1 1 calc R . . H21C H 0.2906 0.2166 -0.2281 0.056 Uiso 1 1 calc R . . C22 C 0.4609(2) 0.2550(4) -0.1462(2) 0.0367(11) Uani 1 1 d . . . H22A H 0.4716 0.1569 -0.1420 0.055 Uiso 1 1 calc R . . H22B H 0.4919 0.3023 -0.1084 0.055 Uiso 1 1 calc R . . H22C H 0.4694 0.2915 -0.1808 0.055 Uiso 1 1 calc R . . C23 C 0.4792(2) 0.1734(4) -0.0079(2) 0.0406(12) Uani 1 1 d . . . H23A H 0.5165 0.2202 0.0268 0.061 Uiso 1 1 calc R . . H23B H 0.4987 0.1450 -0.0373 0.061 Uiso 1 1 calc R . . H23C H 0.4628 0.0926 0.0069 0.061 Uiso 1 1 calc R . . C24 C 0.3852(2) 0.2986(4) 0.00572(19) 0.0368(11) Uani 1 1 d . . . H24A H 0.4234 0.3172 0.0463 0.055 Uiso 1 1 calc R . . H24B H 0.3572 0.2195 0.0083 0.055 Uiso 1 1 calc R . . H24C H 0.3539 0.3787 -0.0083 0.055 Uiso 1 1 calc R . . C25 C 0.0655(2) 0.8451(4) -0.2559(2) 0.0452(13) Uani 1 1 d . . . H25A H 0.0204 0.8108 -0.2564 0.068 Uiso 0.50 1 calc PR . . H25B H 0.0593 0.8651 -0.2980 0.068 Uiso 0.50 1 calc PR . . H25C H 0.0795 0.9289 -0.2312 0.068 Uiso 0.50 1 calc PR . . H25D H 0.0857 0.9258 -0.2674 0.068 Uiso 0.50 1 calc PR . . H25E H 0.0468 0.8714 -0.2258 0.068 Uiso 0.50 1 calc PR . . H25F H 0.0266 0.8076 -0.2926 0.068 Uiso 0.50 1 calc PR . . C26 C 0.1229(2) 0.7388(4) -0.22844(19) 0.0303(10) Uani 1 1 d . . . C27 C 0.1053(2) 0.6004(4) -0.23160(19) 0.0337(11) Uani 1 1 d . . . H27A H 0.0565 0.5736 -0.2509 0.040 Uiso 1 1 calc R . . C28 C 0.1578(2) 0.5015(4) -0.20706(18) 0.0296(10) Uani 1 1 d . . . H28A H 0.1440 0.4082 -0.2093 0.035 Uiso 1 1 calc R . . C29 C 0.2304(2) 0.5348(4) -0.17912(18) 0.0257(10) Uani 1 1 d . . . C30 C 0.2477(2) 0.6740(4) -0.17686(18) 0.0284(10) Uani 1 1 d . . . H30A H 0.2965 0.7013 -0.1587 0.034 Uiso 1 1 calc R . . C31 C 0.1950(2) 0.7721(4) -0.20061(18) 0.0318(10) Uani 1 1 d . . . H31A H 0.2086 0.8657 -0.1978 0.038 Uiso 1 1 calc R . . C32 C 0.2873(2) 0.4297(4) -0.15524(18) 0.0261(10) Uani 1 1 d . . . C33 C 0.2854(2) 0.3138(4) -0.12438(17) 0.0228(9) Uani 1 1 d . . . C34 C 0.2240(2) 0.2776(4) -0.10949(17) 0.0229(9) Uani 1 1 d . . . C35 C 0.1802(2) 0.1654(4) -0.13705(18) 0.0281(10) Uani 1 1 d . . . H35A H 0.1928 0.1061 -0.1625 0.034 Uiso 1 1 calc R . . C36 C 0.1191(2) 0.1389(4) -0.12802(19) 0.0325(11) Uani 1 1 d . . . H36A H 0.0897 0.0635 -0.1486 0.039 Uiso 1 1 calc R . . C37 C 0.0995(2) 0.2196(5) -0.0896(2) 0.0335(11) Uani 1 1 d . . . C38 C 0.1435(2) 0.3282(5) -0.0610(2) 0.0390(12) Uani 1 1 d . . . H38A H 0.1318 0.3848 -0.0342 0.047 Uiso 1 1 calc R . . C39 C 0.2045(2) 0.3571(4) -0.07047(19) 0.0335(11) Uani 1 1 d . . . H39A H 0.2337 0.4327 -0.0498 0.040 Uiso 1 1 calc R . . C40 C 0.0331(2) 0.1895(5) -0.0792(2) 0.0538(14) Uani 1 1 d . . . H40A H 0.0043 0.1202 -0.1086 0.081 Uiso 0.50 1 calc PR . . H40B H 0.0049 0.2735 -0.0849 0.081 Uiso 0.50 1 calc PR . . H40C H 0.0470 0.1554 -0.0373 0.081 Uiso 0.50 1 calc PR . . H40D H 0.0332 0.2458 -0.0452 0.081 Uiso 0.50 1 calc PR . . H40E H 0.0326 0.0925 -0.0690 0.081 Uiso 0.50 1 calc PR . . H40F H -0.0095 0.2106 -0.1166 0.081 Uiso 0.50 1 calc PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.025(3) 0.026(3) 0.029(3) -0.005(2) 0.016(2) -0.001(2) B2 0.026(3) 0.027(3) 0.023(3) -0.001(2) 0.012(2) 0.003(2) N1 0.0296(19) 0.0216(18) 0.027(2) 0.0045(16) 0.0144(16) -0.0010(16) N2 0.026(2) 0.023(2) 0.036(2) -0.0040(17) 0.0147(19) 0.0018(17) Cl1 0.0397(7) 0.0387(6) 0.0421(7) 0.0003(6) 0.0283(6) 0.0043(5) Cl2 0.0301(6) 0.0230(6) 0.0467(7) -0.0051(5) 0.0166(5) -0.0033(5) Cl3 0.0271(6) 0.0295(6) 0.0340(6) 0.0022(5) 0.0115(5) 0.0011(5) C1 0.038(3) 0.042(3) 0.024(3) -0.003(2) 0.014(2) 0.002(2) C2 0.047(3) 0.029(2) 0.049(3) 0.015(2) 0.032(3) 0.008(2) C3 0.047(3) 0.025(2) 0.055(3) -0.003(2) 0.025(3) 0.005(2) C4 0.045(3) 0.038(3) 0.039(3) -0.009(2) 0.029(2) -0.006(2) C5 0.035(3) 0.031(3) 0.045(3) 0.004(2) 0.014(2) 0.003(2) C6 0.027(2) 0.022(2) 0.024(2) 0.0004(19) 0.012(2) 0.0008(19) C7 0.035(3) 0.020(2) 0.029(3) 0.0008(19) 0.016(2) -0.001(2) C8 0.025(2) 0.026(2) 0.025(2) -0.0045(19) 0.0092(19) -0.0036(19) C9 0.028(2) 0.024(2) 0.019(2) 0.0015(18) 0.0125(19) 0.0002(19) C10 0.033(3) 0.019(2) 0.040(3) -0.001(2) 0.015(2) -0.003(2) C11 0.023(2) 0.035(3) 0.036(3) 0.003(2) 0.008(2) -0.002(2) C12 0.027(2) 0.019(2) 0.024(2) -0.0050(18) 0.0114(19) -0.0039(18) C13 0.031(2) 0.018(2) 0.023(2) -0.0060(18) 0.014(2) -0.0064(18) C14 0.022(2) 0.020(2) 0.022(2) -0.0013(18) 0.0096(19) 0.0043(18) C15 0.029(2) 0.028(2) 0.024(2) 0.006(2) 0.006(2) -0.003(2) C16 0.025(2) 0.034(3) 0.035(3) 0.001(2) 0.002(2) -0.007(2) C17 0.030(3) 0.032(3) 0.031(3) 0.008(2) 0.014(2) 0.002(2) C18 0.030(3) 0.041(3) 0.026(3) 0.013(2) 0.015(2) 0.007(2) C19 0.023(2) 0.033(3) 0.026(2) 0.001(2) 0.010(2) 0.004(2) C20 0.047(3) 0.055(3) 0.063(4) 0.020(3) 0.024(3) -0.011(3) B3 0.032(3) 0.030(3) 0.025(3) -0.001(2) 0.014(2) -0.003(2) B4 0.033(3) 0.025(3) 0.027(3) -0.001(2) 0.015(2) -0.003(2) N3 0.0229(19) 0.033(2) 0.029(2) -0.0047(17) 0.0150(17) -0.0015(16) N4 0.031(2) 0.027(2) 0.030(2) 0.0030(17) 0.0147(18) 0.0007(18) Cl4 0.0342(6) 0.0552(8) 0.0341(7) 0.0103(6) 0.0188(5) 0.0020(6) Cl5 0.0346(6) 0.0310(6) 0.0379(7) -0.0018(5) 0.0135(5) -0.0079(5) Cl6 0.0415(7) 0.0238(6) 0.0516(8) -0.0061(5) 0.0253(6) -0.0022(5) C21 0.036(3) 0.045(3) 0.033(3) -0.012(2) 0.016(2) -0.005(2) C22 0.035(3) 0.040(3) 0.042(3) -0.004(2) 0.022(2) 0.001(2) C23 0.038(3) 0.039(3) 0.041(3) 0.003(2) 0.011(2) 0.011(2) C24 0.039(3) 0.044(3) 0.030(3) -0.006(2) 0.017(2) -0.002(2) C25 0.043(3) 0.040(3) 0.053(3) 0.006(2) 0.020(3) 0.007(2) C26 0.037(3) 0.032(3) 0.027(3) 0.004(2) 0.018(2) 0.005(2) C27 0.024(2) 0.039(3) 0.038(3) 0.002(2) 0.012(2) -0.001(2) C28 0.032(3) 0.026(2) 0.033(3) 0.003(2) 0.016(2) 0.000(2) C29 0.029(2) 0.029(2) 0.024(2) 0.0002(19) 0.016(2) -0.004(2) C30 0.025(2) 0.034(3) 0.028(3) -0.005(2) 0.012(2) -0.004(2) C31 0.041(3) 0.032(3) 0.026(3) -0.003(2) 0.017(2) -0.001(2) C32 0.030(2) 0.025(2) 0.026(2) -0.0053(19) 0.013(2) -0.0020(19) C33 0.027(2) 0.023(2) 0.023(2) -0.0060(19) 0.0139(19) -0.0029(19) C34 0.024(2) 0.024(2) 0.023(2) 0.0039(18) 0.012(2) 0.0044(18) C35 0.029(2) 0.030(2) 0.027(3) -0.001(2) 0.014(2) 0.002(2) C36 0.029(3) 0.034(3) 0.033(3) 0.005(2) 0.011(2) -0.006(2) C37 0.027(2) 0.043(3) 0.032(3) 0.012(2) 0.014(2) 0.009(2) C38 0.042(3) 0.043(3) 0.042(3) -0.001(2) 0.027(2) 0.011(2) C39 0.031(3) 0.034(3) 0.041(3) -0.004(2) 0.020(2) -0.001(2) C40 0.040(3) 0.069(4) 0.067(4) 0.016(3) 0.035(3) 0.002(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 B1 C12 1.594(6) . ? B1 N1 1.607(6) . ? B1 Cl1 1.862(5) . ? B1 Cl2 1.904(5) . ? B2 N1 1.604(5) . ? B2 N2 1.616(6) . ? B2 C13 1.618(6) . ? B2 Cl3 1.867(5) . ? N1 C2 1.501(5) . ? N1 C1 1.510(5) . ? N2 C3 1.497(5) . ? N2 C4 1.498(5) . ? C5 C6 1.502(5) . ? C6 C7 1.388(5) . ? C6 C11 1.394(5) . ? C7 C8 1.381(5) . ? C8 C9 1.400(5) . ? C9 C10 1.391(5) . ? C9 C12 1.489(5) . ? C10 C11 1.376(5) . ? C12 C13 1.354(5) . ? C13 C14 1.491(5) . ? C14 C15 1.386(5) . ? C14 C19 1.392(5) . ? C15 C16 1.378(5) . ? C16 C17 1.387(5) . ? C17 C18 1.379(6) . ? C17 C20 1.518(5) . ? C18 C19 1.387(5) . ? B3 C32 1.586(6) . ? B3 N3 1.626(6) . ? B3 Cl4 1.867(5) . ? B3 Cl5 1.911(5) . ? B4 C33 1.599(6) . ? B4 N3 1.615(5) . ? B4 N4 1.621(6) . ? B4 Cl6 1.865(5) . ? N3 C22 1.490(5) . ? N3 C21 1.507(5) . ? N4 C23 1.495(5) . ? N4 C24 1.498(5) . ? C25 C26 1.503(6) . ? C26 C31 1.386(6) . ? C26 C27 1.394(6) . ? C27 C28 1.384(5) . ? C28 C29 1.395(5) . ? C29 C30 1.402(5) . ? C29 C32 1.481(5) . ? C30 C31 1.379(5) . ? C32 C33 1.361(5) . ? C33 C34 1.486(5) . ? C34 C39 1.392(5) . ? C34 C35 1.398(5) . ? C35 C36 1.380(5) . ? C36 C37 1.390(6) . ? C37 C38 1.378(6) . ? C37 C40 1.509(5) . ? C38 C39 1.389(5) . ? 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 C12 B1 N1 102.8(3) . . ? C12 B1 Cl1 115.7(3) . . ? N1 B1 Cl1 111.6(3) . . ? C12 B1 Cl2 111.3(3) . . ? N1 B1 Cl2 108.7(3) . . ? Cl1 B1 Cl2 106.6(2) . . ? N1 B2 N2 111.5(3) . . ? N1 B2 C13 101.6(3) . . ? N2 B2 C13 109.7(3) . . ? N1 B2 Cl3 111.6(3) . . ? N2 B2 Cl3 104.3(3) . . ? C13 B2 Cl3 118.2(3) . . ? C2 N1 C1 105.2(3) . . ? C2 N1 B2 118.5(3) . . ? C1 N1 B2 107.9(3) . . ? C2 N1 B1 113.8(3) . . ? C1 N1 B1 109.9(3) . . ? B2 N1 B1 101.3(3) . . ? C3 N2 C4 107.3(3) . . ? C3 N2 B2 119.0(3) . . ? C4 N2 B2 111.2(3) . . ? C7 C6 C11 116.9(4) . . ? C7 C6 C5 122.3(4) . . ? C11 C6 C5 120.7(4) . . ? C8 C7 C6 122.5(4) . . ? C7 C8 C9 120.5(4) . . ? C10 C9 C8 116.7(4) . . ? C10 C9 C12 119.3(4) . . ? C8 C9 C12 123.8(4) . . ? C11 C10 C9 122.5(4) . . ? C10 C11 C6 120.8(4) . . ? C13 C12 C9 127.8(3) . . ? C13 C12 B1 111.3(3) . . ? C9 C12 B1 120.9(3) . . ? C12 C13 C14 124.2(4) . . ? C12 C13 B2 109.7(3) . . ? C14 C13 B2 126.0(3) . . ? C15 C14 C19 116.7(4) . . ? C15 C14 C13 120.8(4) . . ? C19 C14 C13 122.5(3) . . ? C16 C15 C14 121.7(4) . . ? C15 C16 C17 121.7(4) . . ? C18 C17 C16 116.7(4) . . ? C18 C17 C20 121.5(4) . . ? C16 C17 C20 121.8(4) . . ? C17 C18 C19 122.0(4) . . ? C18 C19 C14 121.2(4) . . ? C32 B3 N3 102.7(3) . . ? C32 B3 Cl4 116.8(3) . . ? N3 B3 Cl4 111.0(3) . . ? C32 B3 Cl5 111.8(3) . . ? N3 B3 Cl5 108.8(3) . . ? Cl4 B3 Cl5 105.7(2) . . ? C33 B4 N3 101.7(3) . . ? C33 B4 N4 112.1(3) . . ? N3 B4 N4 108.9(3) . . ? C33 B4 Cl6 116.0(3) . . ? N3 B4 Cl6 112.3(3) . . ? N4 B4 Cl6 105.9(3) . . ? C22 N3 C21 105.1(3) . . ? C22 N3 B4 118.8(3) . . ? C21 N3 B4 109.0(3) . . ? C22 N3 B3 115.0(3) . . ? C21 N3 B3 108.4(3) . . ? B4 N3 B3 100.3(3) . . ? C23 N4 C24 107.6(3) . . ? C23 N4 B4 118.5(3) . . ? C24 N4 B4 112.2(3) . . ? C31 C26 C27 117.1(4) . . ? C31 C26 C25 122.3(4) . . ? C27 C26 C25 120.6(4) . . ? C28 C27 C26 121.1(4) . . ? C27 C28 C29 121.9(4) . . ? C28 C29 C30 116.6(4) . . ? C28 C29 C32 122.6(4) . . ? C30 C29 C32 120.7(4) . . ? C31 C30 C29 121.1(4) . . ? C30 C31 C26 122.2(4) . . ? C33 C32 C29 126.3(4) . . ? C33 C32 B3 110.4(4) . . ? C29 C32 B3 123.2(3) . . ? C32 C33 C34 123.0(4) . . ? C32 C33 B4 110.9(3) . . ? C34 C33 B4 126.1(3) . . ? C39 C34 C35 116.6(4) . . ? C39 C34 C33 122.2(4) . . ? C35 C34 C33 121.1(3) . . ? C36 C35 C34 121.4(4) . . ? C35 C36 C37 121.7(4) . . ? C38 C37 C36 117.1(4) . . ? C38 C37 C40 121.3(4) . . ? C36 C37 C40 121.6(4) . . ? C37 C38 C39 121.8(4) . . ? C38 C39 C34 121.4(4) . . ? 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 B2 N1 C2 -43.5(5) . . . . ? C13 B2 N1 C2 -160.3(3) . . . . ? Cl3 B2 N1 C2 72.8(4) . . . . ? N2 B2 N1 C1 -162.8(3) . . . . ? C13 B2 N1 C1 80.4(4) . . . . ? Cl3 B2 N1 C1 -46.5(4) . . . . ? N2 B2 N1 B1 81.8(4) . . . . ? C13 B2 N1 B1 -35.0(4) . . . . ? Cl3 B2 N1 B1 -161.9(3) . . . . ? C12 B1 N1 C2 160.8(3) . . . . ? Cl1 B1 N1 C2 -74.6(4) . . . . ? Cl2 B1 N1 C2 42.7(4) . . . . ? C12 B1 N1 C1 -81.5(4) . . . . ? Cl1 B1 N1 C1 43.1(4) . . . . ? Cl2 B1 N1 C1 160.4(3) . . . . ? C12 B1 N1 B2 32.4(4) . . . . ? Cl1 B1 N1 B2 157.1(3) . . . . ? Cl2 B1 N1 B2 -85.7(3) . . . . ? N1 B2 N2 C3 78.9(4) . . . . ? C13 B2 N2 C3 -169.3(3) . . . . ? Cl3 B2 N2 C3 -41.7(4) . . . . ? N1 B2 N2 C4 -155.6(3) . . . . ? C13 B2 N2 C4 -43.9(4) . . . . ? Cl3 B2 N2 C4 83.7(3) . . . . ? C11 C6 C7 C8 1.5(6) . . . . ? C5 C6 C7 C8 -176.0(4) . . . . ? C6 C7 C8 C9 0.2(6) . . . . ? C7 C8 C9 C10 -1.6(5) . . . . ? C7 C8 C9 C12 174.4(4) . . . . ? C8 C9 C10 C11 1.4(6) . . . . ? C12 C9 C10 C11 -174.8(4) . . . . ? C9 C10 C11 C6 0.2(6) . . . . ? C7 C6 C11 C10 -1.7(6) . . . . ? C5 C6 C11 C10 175.9(4) . . . . ? C10 C9 C12 C13 -136.0(4) . . . . ? C8 C9 C12 C13 48.1(6) . . . . ? C10 C9 C12 B1 44.6(5) . . . . ? C8 C9 C12 B1 -131.3(4) . . . . ? N1 B1 C12 C13 -17.7(4) . . . . ? Cl1 B1 C12 C13 -139.5(3) . . . . ? Cl2 B1 C12 C13 98.6(4) . . . . ? N1 B1 C12 C9 161.8(3) . . . . ? Cl1 B1 C12 C9 39.9(5) . . . . ? Cl2 B1 C12 C9 -82.0(4) . . . . ? C9 C12 C13 C14 -1.6(6) . . . . ? B1 C12 C13 C14 177.8(3) . . . . ? C9 C12 C13 B2 175.1(4) . . . . ? B1 C12 C13 B2 -5.5(4) . . . . ? N1 B2 C13 C12 26.4(4) . . . . ? N2 B2 C13 C12 -91.7(4) . . . . ? Cl3 B2 C13 C12 148.9(3) . . . . ? N1 B2 C13 C14 -157.0(3) . . . . ? N2 B2 C13 C14 84.9(5) . . . . ? Cl3 B2 C13 C14 -34.5(5) . . . . ? C12 C13 C14 C15 -126.0(4) . . . . ? B2 C13 C14 C15 57.9(5) . . . . ? C12 C13 C14 C19 52.8(5) . . . . ? B2 C13 C14 C19 -123.3(4) . . . . ? C19 C14 C15 C16 -1.4(6) . . . . ? C13 C14 C15 C16 177.5(4) . . . . ? C14 C15 C16 C17 2.9(7) . . . . ? C15 C16 C17 C18 -2.7(6) . . . . ? C15 C16 C17 C20 177.6(4) . . . . ? C16 C17 C18 C19 1.2(6) . . . . ? C20 C17 C18 C19 -179.1(4) . . . . ? C17 C18 C19 C14 0.2(6) . . . . ? C15 C14 C19 C18 -0.2(6) . . . . ? C13 C14 C19 C18 -179.0(4) . . . . ? C33 B4 N3 C22 161.1(3) . . . . ? N4 B4 N3 C22 42.6(5) . . . . ? Cl6 B4 N3 C22 -74.3(4) . . . . ? C33 B4 N3 C21 -78.7(4) . . . . ? N4 B4 N3 C21 162.8(3) . . . . ? Cl6 B4 N3 C21 45.9(4) . . . . ? C33 B4 N3 B3 35.0(4) . . . . ? N4 B4 N3 B3 -83.5(4) . . . . ? Cl6 B4 N3 B3 159.7(3) . . . . ? C32 B3 N3 C22 -162.7(3) . . . . ? Cl4 B3 N3 C22 71.7(4) . . . . ? Cl5 B3 N3 C22 -44.1(4) . . . . ? C32 B3 N3 C21 80.0(4) . . . . ? Cl4 B3 N3 C21 -45.5(4) . . . . ? Cl5 B3 N3 C21 -161.4(3) . . . . ? C32 B3 N3 B4 -34.1(4) . . . . ? Cl4 B3 N3 B4 -159.7(3) . . . . ? Cl5 B3 N3 B4 84.5(3) . . . . ? C33 B4 N4 C23 163.6(3) . . . . ? N3 B4 N4 C23 -84.7(4) . . . . ? Cl6 B4 N4 C23 36.2(4) . . . . ? C33 B4 N4 C24 37.1(5) . . . . ? N3 B4 N4 C24 148.9(3) . . . . ? Cl6 B4 N4 C24 -90.2(3) . . . . ? C31 C26 C27 C28 0.9(6) . . . . ? C25 C26 C27 C28 179.3(4) . . . . ? C26 C27 C28 C29 -1.1(6) . . . . ? C27 C28 C29 C30 0.2(6) . . . . ? C27 C28 C29 C32 -177.1(4) . . . . ? C28 C29 C30 C31 0.7(6) . . . . ? C32 C29 C30 C31 178.1(4) . . . . ? C29 C30 C31 C26 -0.9(6) . . . . ? C27 C26 C31 C30 0.0(6) . . . . ? C25 C26 C31 C30 -178.3(4) . . . . ? C28 C29 C32 C33 -40.5(6) . . . . ? C30 C29 C32 C33 142.3(4) . . . . ? C28 C29 C32 B3 136.9(4) . . . . ? C30 C29 C32 B3 -40.3(6) . . . . ? N3 B3 C32 C33 20.8(4) . . . . ? Cl4 B3 C32 C33 142.5(3) . . . . ? Cl5 B3 C32 C33 -95.7(4) . . . . ? N3 B3 C32 C29 -156.9(3) . . . . ? Cl4 B3 C32 C29 -35.2(5) . . . . ? Cl5 B3 C32 C29 86.6(4) . . . . ? C29 C32 C33 C34 -0.9(6) . . . . ? B3 C32 C33 C34 -178.5(3) . . . . ? C29 C32 C33 B4 -179.8(4) . . . . ? B3 C32 C33 B4 2.5(5) . . . . ? N3 B4 C33 C32 -24.9(4) . . . . ? N4 B4 C33 C32 91.2(4) . . . . ? Cl6 B4 C33 C32 -147.0(3) . . . . ? N3 B4 C33 C34 156.2(3) . . . . ? N4 B4 C33 C34 -87.7(5) . . . . ? Cl6 B4 C33 C34 34.1(5) . . . . ? C32 C33 C34 C39 -64.0(6) . . . . ? B4 C33 C34 C39 114.8(5) . . . . ? C32 C33 C34 C35 112.3(4) . . . . ? B4 C33 C34 C35 -68.9(5) . . . . ? C39 C34 C35 C36 2.8(6) . . . . ? C33 C34 C35 C36 -173.7(4) . . . . ? C34 C35 C36 C37 -2.1(6) . . . . ? C35 C36 C37 C38 0.4(6) . . . . ? C35 C36 C37 C40 -179.3(4) . . . . ? C36 C37 C38 C39 0.6(6) . . . . ? C40 C37 C38 C39 -179.8(4) . . . . ? C37 C38 C39 C34 0.2(7) . . . . ? C35 C34 C39 C38 -1.9(6) . . . . ? C33 C34 C39 C38 174.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.357 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.070