Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 # 1. SUBMISSION DETAILS _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 _publ_contact_letter ; Please consider this CIF submission for publication in Dalton Transactions ; # 2. TITLE AND AUTHOR LIST _publ_section_title ; Synthesis and structures of boron halides supported by the C6F5-substituted beta-diketiminate ligand [HC(CMe)2(NC6F5)2] ; loop_ _publ_author_name _publ_author_address 'Alan H. Cowley' ; Department of Chemistry and Biochemistry University of Texas-Austin 1 University Station, A5300 Austin, TX 78701 USA ; 'Dragoslav Vidovic' ; 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 ; 'Gregor Reeske' ; 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. Sluis, P. v.d. & Spek, A. L. (1990). SQUEEZE. Acta Cryst. A46, 194-201. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _publ_section_figure_captions ; ; _publ_section_exptl_prep ; ; # Attachment 'Compound51.cif' data_try1_Compound51 _database_code_depnum_ccdc_archive 'CCDC 670302' _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H7 B Cl2 F10 N2' _chemical_formula_sum 'C17 H7 B Cl2 F10 N2' _chemical_formula_weight 510.96 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn _symmetry_space_group_name_Hall -P2n2ab loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 21.996(4) _cell_length_b 7.2823(15) _cell_length_c 11.470(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1837.2(6) _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 0.03 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.847 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.461 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.986 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 '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 3857 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0401 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2104 _reflns_number_gt 1429 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XL SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _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^)+(0.0584P)^2^+0.3893P] 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 2104 _refine_ls_number_parameters 147 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0710 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1111 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.05027(9) 0.6086(3) 0.70643(18) 0.0297(5) Uani 1 1 d . . . C2 C 0.0000 0.6979(4) 0.7500 0.0325(7) Uani 1 2 d S . . H2 H 0.0000 0.8257 0.7500 0.039 Uiso 1 2 calc SR . . C3 C 0.10225(10) 0.7147(3) 0.6565(2) 0.0401(6) Uani 1 1 d U . . H3A H 0.1390 0.6821 0.6965 0.060 Uiso 1 1 calc R . . H3B H 0.0948 0.8438 0.6657 0.060 Uiso 1 1 calc R . . H3C H 0.1063 0.6864 0.5751 0.060 Uiso 1 1 calc R . . C4 C 0.10551(9) 0.3309(3) 0.66580(19) 0.0289(5) Uani 1 1 d . . . C5 C 0.15250(9) 0.2810(3) 0.73990(19) 0.0327(5) Uani 1 1 d . . . C6 C 0.20118(9) 0.1786(3) 0.7004(2) 0.0372(6) Uani 1 1 d . . . C7 C 0.20399(10) 0.1277(3) 0.5853(2) 0.0402(6) Uani 1 1 d . . . C8 C 0.15916(10) 0.1797(3) 0.5089(2) 0.0387(6) Uani 1 1 d . . . C9 C 0.11093(9) 0.2823(3) 0.54907(19) 0.0342(5) Uani 1 1 d . . . B1 B 0.0000 0.3033(5) 0.7500 0.0294(7) Uani 1 2 d S . . N1 N 0.05246(7) 0.4239(2) 0.70781(15) 0.0274(4) Uani 1 1 d . . . F1 F 0.15223(5) 0.33546(19) 0.85129(11) 0.0423(4) Uani 1 1 d . . . F2 F 0.24623(5) 0.1315(2) 0.77320(13) 0.0537(4) Uani 1 1 d . . . F3 F 0.25181(6) 0.0302(2) 0.54626(13) 0.0598(4) Uani 1 1 d . . . F4 F 0.16274(7) 0.1335(2) 0.39610(13) 0.0550(4) Uani 1 1 d . . . F5 F 0.06920(6) 0.33990(19) 0.47276(11) 0.0443(4) Uani 1 1 d . . . Cl1 Cl 0.02615(2) 0.14811(7) 0.87122(5) 0.03293(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 0.0302(11) 0.0305(12) 0.0283(11) 0.0024(9) -0.0100(9) -0.0037(9) C2 0.0349(16) 0.0217(15) 0.0409(18) 0.000 -0.0090(14) 0.000 C3 0.0386(12) 0.0329(12) 0.0488(15) 0.0050(10) -0.0042(10) -0.0106(10) C4 0.0280(11) 0.0261(11) 0.0326(12) 0.0010(9) 0.0040(9) -0.0029(8) C5 0.0293(12) 0.0367(12) 0.0321(12) 0.0021(10) 0.0005(9) -0.0052(9) C6 0.0252(11) 0.0412(13) 0.0451(14) 0.0101(10) -0.0002(10) 0.0008(10) C7 0.0318(13) 0.0353(13) 0.0534(15) 0.0020(11) 0.0135(11) 0.0043(10) C8 0.0396(13) 0.0419(13) 0.0345(13) -0.0055(10) 0.0092(11) -0.0076(10) C9 0.0326(12) 0.0369(12) 0.0331(12) 0.0041(10) -0.0017(10) -0.0048(10) B1 0.0302(17) 0.0260(17) 0.0320(19) 0.000 -0.0007(15) 0.000 N1 0.0272(9) 0.0255(9) 0.0295(10) 0.0016(7) -0.0016(7) 0.0006(7) F1 0.0326(7) 0.0615(9) 0.0327(8) -0.0022(6) -0.0038(5) -0.0030(6) F2 0.0295(7) 0.0735(11) 0.0581(9) 0.0153(7) -0.0033(6) 0.0077(6) F3 0.0467(8) 0.0590(10) 0.0736(11) -0.0005(8) 0.0207(7) 0.0154(7) F4 0.0579(9) 0.0671(10) 0.0400(9) -0.0120(7) 0.0143(7) -0.0032(7) F5 0.0438(8) 0.0601(9) 0.0291(7) 0.0055(6) -0.0043(6) -0.0009(6) Cl1 0.0348(3) 0.0296(3) 0.0344(3) 0.0049(2) -0.0025(2) 0.0018(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.346(3) . ? C1 C2 1.377(3) . ? C1 C3 1.494(3) . ? C2 C1 1.377(3) 3_556 ? C2 H2 0.9300 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C5 1.387(3) . ? C4 C9 1.390(3) . ? C4 N1 1.432(3) . ? C5 F1 1.338(2) . ? C5 C6 1.381(3) . ? C6 F2 1.341(2) . ? C6 C7 1.372(4) . ? C7 F3 1.346(2) . ? C7 C8 1.373(3) . ? C8 F4 1.340(3) . ? C8 C9 1.377(3) . ? C9 F5 1.336(2) . ? B1 N1 1.529(3) 3_556 ? B1 N1 1.529(3) . ? B1 Cl1 1.882(2) 3_556 ? B1 Cl1 1.882(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 119.8(2) . . ? N1 C1 C3 119.60(19) . . ? C2 C1 C3 120.6(2) . . ? C1 C2 C1 123.6(3) . 3_556 ? C1 C2 H2 118.2 . . ? C1 C2 H2 118.2 3_556 . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C5 C4 C9 117.3(2) . . ? C5 C4 N1 121.67(19) . . ? C9 C4 N1 120.95(19) . . ? F1 C5 C6 118.50(19) . . ? F1 C5 C4 120.28(19) . . ? C6 C5 C4 121.2(2) . . ? F2 C6 C7 119.8(2) . . ? F2 C6 C5 120.4(2) . . ? C7 C6 C5 119.8(2) . . ? F3 C7 C6 119.9(2) . . ? F3 C7 C8 119.6(2) . . ? C6 C7 C8 120.5(2) . . ? F4 C8 C7 120.3(2) . . ? F4 C8 C9 120.3(2) . . ? C7 C8 C9 119.3(2) . . ? F5 C9 C8 118.7(2) . . ? F5 C9 C4 119.46(19) . . ? C8 C9 C4 121.8(2) . . ? N1 B1 N1 109.9(2) 3_556 . ? N1 B1 Cl1 110.37(6) 3_556 3_556 ? N1 B1 Cl1 109.99(7) . 3_556 ? N1 B1 Cl1 109.99(7) 3_556 . ? N1 B1 Cl1 110.37(6) . . ? Cl1 B1 Cl1 106.17(17) 3_556 . ? C1 N1 C4 119.83(17) . . ? C1 N1 B1 123.41(18) . . ? C4 N1 B1 116.75(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C1 -1.68(14) . . . 3_556 ? C3 C1 C2 C1 177.7(2) . . . 3_556 ? C9 C4 C5 F1 175.02(18) . . . . ? N1 C4 C5 F1 -6.9(3) . . . . ? C9 C4 C5 C6 -3.3(3) . . . . ? N1 C4 C5 C6 174.77(19) . . . . ? F1 C5 C6 F2 1.7(3) . . . . ? C4 C5 C6 F2 -179.99(19) . . . . ? F1 C5 C6 C7 -177.16(19) . . . . ? C4 C5 C6 C7 1.2(3) . . . . ? F2 C6 C7 F3 0.2(3) . . . . ? C5 C6 C7 F3 179.05(19) . . . . ? F2 C6 C7 C8 -178.00(19) . . . . ? C5 C6 C7 C8 0.8(3) . . . . ? F3 C7 C8 F4 0.2(3) . . . . ? C6 C7 C8 F4 178.4(2) . . . . ? F3 C7 C8 C9 -178.82(19) . . . . ? C6 C7 C8 C9 -0.6(3) . . . . ? F4 C8 C9 F5 -2.4(3) . . . . ? C7 C8 C9 F5 176.65(19) . . . . ? F4 C8 C9 C4 179.3(2) . . . . ? C7 C8 C9 C4 -1.7(3) . . . . ? C5 C4 C9 F5 -174.74(18) . . . . ? N1 C4 C9 F5 7.2(3) . . . . ? C5 C4 C9 C8 3.6(3) . . . . ? N1 C4 C9 C8 -174.52(19) . . . . ? C2 C1 N1 C4 -178.08(15) . . . . ? C3 C1 N1 C4 2.5(3) . . . . ? C2 C1 N1 B1 3.3(3) . . . . ? C3 C1 N1 B1 -176.06(15) . . . . ? C5 C4 N1 C1 92.7(2) . . . . ? C9 C4 N1 C1 -89.3(2) . . . . ? C5 C4 N1 B1 -88.6(2) . . . . ? C9 C4 N1 B1 89.4(2) . . . . ? N1 B1 N1 C1 -1.69(14) 3_556 . . . ? Cl1 B1 N1 C1 120.0(2) 3_556 . . . ? Cl1 B1 N1 C1 -123.17(19) . . . . ? N1 B1 N1 C4 179.69(18) 3_556 . . . ? Cl1 B1 N1 C4 -58.61(19) 3_556 . . . ? Cl1 B1 N1 C4 58.21(19) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.318 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.063 # Attachment 'Compound61.cif' data_ccddvgr039_Compound61 _database_code_depnum_ccdc_archive 'CCDC 670303' _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H7 B Br2 F10 N2' _chemical_formula_sum 'C17 H7 B Br2 F10 N2' _chemical_formula_weight 599.88 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M pbna _symmetry_space_group_name_Hall -p2ac2b loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x, -y+1/2, -z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x, y-1/2, z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.457(5) _cell_length_b 11.566(5) _cell_length_c 22.002(5) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_volume 1897.6(16) _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 stick _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.100 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 4.376 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.597 _exptl_absorpt_correction_T_max 0.646 _exptl_absorpt_process_details 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _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 \f-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6513 _diffrn_reflns_av_R_equivalents 0.0492 _diffrn_reflns_av_sigmaI/netI 0.0512 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 27.38 _reflns_number_total 2133 _reflns_number_gt 1614 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _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^)+(0.0000P)^2^+9.6125P] 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 2133 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0826 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1068 _refine_ls_wR_factor_gt 0.0990 _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_restrained_S_all 1.149 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6601(7) 0.3317(5) 0.6061(2) 0.0328(12) Uani 1 1 d . . . C2 C 0.7096(8) 0.2570(5) 0.6524(3) 0.0355(13) Uani 1 1 d . . . C3 C 0.8150(8) 0.2952(5) 0.7010(3) 0.0429(15) Uani 1 1 d . . . C4 C 0.8646(9) 0.4089(6) 0.7044(3) 0.0455(15) Uani 1 1 d . . . C5 C 0.8094(8) 0.4855(5) 0.6603(3) 0.0435(15) Uani 1 1 d . . . C6 C 0.7074(8) 0.4471(5) 0.6128(3) 0.0368(13) Uani 1 1 d . . . C7 C 0.3901(7) 0.2912(4) 0.5505(2) 0.0313(12) Uani 1 1 d . . . C8 C 0.2864(8) 0.3370(5) 0.6038(3) 0.0430(15) Uani 1 1 d . . . H8A H 0.3234 0.2975 0.6400 0.064 Uiso 1 1 calc R . . H8B H 0.1606 0.3245 0.5972 0.064 Uiso 1 1 calc R . . H8C H 0.3089 0.4183 0.6081 0.064 Uiso 1 1 calc R . . C9 C 0.3031(10) 0.2500 0.5000 0.0370(19) Uani 1 2 d S . . H9 H 0.1784 0.2500 0.5000 0.044 Uiso 1 2 calc SR . . B1 B 0.6868(11) 0.2500 0.5000 0.0299(19) Uani 1 2 d S . . N1 N 0.5704(5) 0.2903(3) 0.55257(19) 0.0276(9) Uani 1 1 d . . . F1 F 0.6547(5) 0.1467(3) 0.65245(14) 0.0462(9) Uani 1 1 d . . . F2 F 0.8616(5) 0.2208(3) 0.74505(15) 0.0596(10) Uani 1 1 d . . . F3 F 0.9633(6) 0.4456(4) 0.75131(18) 0.0670(11) Uani 1 1 d . . . F4 F 0.8549(6) 0.5974(3) 0.66476(18) 0.0608(10) Uani 1 1 d . . . F5 F 0.6475(5) 0.5244(3) 0.57192(15) 0.0468(9) Uani 1 1 d . . . Br1 Br 0.85465(7) 0.11916(4) 0.52738(2) 0.03371(17) 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 0.030(3) 0.035(3) 0.034(3) 0.001(2) 0.002(3) 0.003(2) C2 0.042(3) 0.028(3) 0.036(3) 0.000(2) 0.006(3) -0.002(2) C3 0.045(4) 0.054(4) 0.030(3) 0.000(3) 0.002(3) 0.010(3) C4 0.045(4) 0.054(4) 0.037(3) -0.017(3) -0.002(3) -0.003(3) C5 0.046(4) 0.037(3) 0.048(4) -0.013(3) 0.009(3) -0.005(3) C6 0.042(3) 0.029(3) 0.039(3) 0.000(2) 0.009(3) 0.007(2) C7 0.031(3) 0.028(3) 0.034(3) 0.011(2) 0.003(3) 0.005(2) C8 0.032(3) 0.051(4) 0.045(4) 0.009(3) 0.005(3) 0.005(3) C9 0.021(4) 0.047(5) 0.043(5) 0.017(4) 0.000 0.000 B1 0.026(4) 0.021(4) 0.043(5) 0.006(3) 0.000 0.000 N1 0.027(2) 0.026(2) 0.029(2) 0.0021(18) 0.000(2) -0.0009(18) F1 0.063(2) 0.0361(18) 0.0400(19) 0.0047(14) 0.0015(18) -0.0038(16) F2 0.082(3) 0.064(2) 0.0327(19) 0.0041(18) -0.008(2) 0.009(2) F3 0.068(3) 0.080(3) 0.053(2) -0.022(2) -0.017(2) -0.007(2) F4 0.077(3) 0.040(2) 0.066(2) -0.0190(17) 0.005(2) -0.012(2) F5 0.063(2) 0.0284(17) 0.049(2) 0.0032(14) 0.0020(18) 0.0085(16) Br1 0.0313(3) 0.0309(3) 0.0389(3) 0.0025(2) -0.0018(3) 0.0052(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.385(7) . ? C1 C6 1.389(7) . ? C1 N1 1.437(7) . ? C2 F1 1.339(6) . ? C2 C3 1.398(8) . ? C3 F2 1.342(7) . ? C3 C4 1.368(9) . ? C4 F3 1.337(7) . ? C4 C5 1.377(9) . ? C5 F4 1.342(7) . ? C5 C6 1.367(8) . ? C6 F5 1.345(6) . ? C7 N1 1.345(6) . ? C7 C9 1.372(6) . ? C7 C8 1.501(8) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C7 1.372(6) 3_556 ? C9 H9 0.9300 . ? B1 N1 1.519(6) 3_556 ? B1 N1 1.519(6) . ? B1 Br1 2.054(5) 3_556 ? B1 Br1 2.054(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 C2 C1 C6 117.0(5) . . ? C2 C1 N1 121.3(5) . . ? C6 C1 N1 121.6(5) . . ? F1 C2 C1 120.9(5) . . ? F1 C2 C3 118.2(5) . . ? C1 C2 C3 121.0(5) . . ? F2 C3 C4 120.4(6) . . ? F2 C3 C2 119.7(6) . . ? C4 C3 C2 119.8(6) . . ? F3 C4 C3 119.8(6) . . ? F3 C4 C5 120.3(6) . . ? C3 C4 C5 120.0(6) . . ? F4 C5 C6 120.7(6) . . ? F4 C5 C4 119.6(6) . . ? C6 C5 C4 119.7(6) . . ? F5 C6 C5 118.7(5) . . ? F5 C6 C1 119.0(5) . . ? C5 C6 C1 122.3(5) . . ? N1 C7 C9 119.8(5) . . ? N1 C7 C8 119.4(5) . . ? C9 C7 C8 120.8(5) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 C7 123.6(7) . 3_556 ? C7 C9 H9 118.2 . . ? C7 C9 H9 118.2 3_556 . ? N1 B1 N1 110.3(6) 3_556 . ? N1 B1 Br1 110.54(16) 3_556 3_556 ? N1 B1 Br1 110.20(16) . 3_556 ? N1 B1 Br1 110.20(16) 3_556 . ? N1 B1 Br1 110.54(16) . . ? Br1 B1 Br1 104.9(4) 3_556 . ? C7 N1 C1 119.4(4) . . ? C7 N1 B1 123.2(5) . . ? C1 N1 B1 117.4(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 C6 C1 C2 F1 173.6(5) . . . . ? N1 C1 C2 F1 -8.9(8) . . . . ? C6 C1 C2 C3 -5.0(8) . . . . ? N1 C1 C2 C3 172.4(5) . . . . ? F1 C2 C3 F2 1.6(8) . . . . ? C1 C2 C3 F2 -179.7(5) . . . . ? F1 C2 C3 C4 -176.1(5) . . . . ? C1 C2 C3 C4 2.5(9) . . . . ? F2 C3 C4 F3 1.3(9) . . . . ? C2 C3 C4 F3 179.1(5) . . . . ? F2 C3 C4 C5 -177.2(5) . . . . ? C2 C3 C4 C5 0.6(9) . . . . ? F3 C4 C5 F4 -0.1(9) . . . . ? C3 C4 C5 F4 178.3(5) . . . . ? F3 C4 C5 C6 -179.5(5) . . . . ? C3 C4 C5 C6 -1.0(9) . . . . ? F4 C5 C6 F5 -2.6(9) . . . . ? C4 C5 C6 F5 176.7(5) . . . . ? F4 C5 C6 C1 178.9(5) . . . . ? C4 C5 C6 C1 -1.7(9) . . . . ? C2 C1 C6 F5 -173.8(5) . . . . ? N1 C1 C6 F5 8.8(8) . . . . ? C2 C1 C6 C5 4.7(9) . . . . ? N1 C1 C6 C5 -172.8(5) . . . . ? N1 C7 C9 C7 -1.4(3) . . . 3_556 ? C8 C7 C9 C7 178.9(5) . . . 3_556 ? C9 C7 N1 C1 -178.8(4) . . . . ? C8 C7 N1 C1 0.9(7) . . . . ? C9 C7 N1 B1 2.7(6) . . . . ? C8 C7 N1 B1 -177.6(4) . . . . ? C2 C1 N1 C7 93.2(6) . . . . ? C6 C1 N1 C7 -89.4(6) . . . . ? C2 C1 N1 B1 -88.2(6) . . . . ? C6 C1 N1 B1 89.1(6) . . . . ? N1 B1 N1 C7 -1.4(3) 3_556 . . . ? Br1 B1 N1 C7 121.0(5) 3_556 . . . ? Br1 B1 N1 C7 -123.5(5) . . . . ? N1 B1 N1 C1 -179.9(4) 3_556 . . . ? Br1 B1 N1 C1 -57.5(5) 3_556 . . . ? Br1 B1 N1 C1 58.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.38 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.849 _refine_diff_density_min -0.412 _refine_diff_density_rms 0.102 # Attachment 'Compound71.cif' data_try1_Compound71 _database_code_depnum_ccdc_archive 'CCDC 670304' _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H7 B F10 I2 N2' _chemical_formula_sum 'C17 H7 B F10 I2 N2' _chemical_formula_weight 693.86 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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 7.372(1) _cell_length_b 11.711(2) _cell_length_c 13.175(2) _cell_angle_alpha 88.476(6) _cell_angle_beta 87.593(6) _cell_angle_gamma 75.717(7) _cell_volume 1101.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.093 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 2.946 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.498 _exptl_absorpt_correction_T_max 0.588 _exptl_absorpt_process_details 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _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 \f-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7532 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0422 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5015 _reflns_number_gt 4253 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _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. One molecule of what appeared to be dichloromethane was found to be badly disordered. Attempts to model the disorder were unsatisfactory. The contributions to the scattering factors due to these solvent molecules were removed by use of the utility SQUEEZE (Sluis and Spek, 1990) in PLATON98 (Spek, 1998). PLATON98 was used as incorporated in WinGX (Farrugia, 1999). ; _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^)+(0.0511P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5015 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0978 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 1.196 _refine_ls_restrained_S_all 1.196 _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 0.3204(5) 0.3541(3) 0.8677(3) 0.0233(7) Uani 1 1 d . . . C2 C 0.2969(5) 0.2421(3) 0.8921(3) 0.0265(8) Uani 1 1 d . . . H2 H 0.2000 0.2335 0.9393 0.032 Uiso 1 1 calc R . . C3 C 0.4138(5) 0.1431(3) 0.8480(3) 0.0253(8) Uani 1 1 d . . . C4 C 0.3525(6) 0.0303(4) 0.8428(4) 0.0398(10) Uani 1 1 d . . . H4A H 0.3238 0.0178 0.7726 0.060 Uiso 1 1 calc R . . H4B H 0.2406 0.0352 0.8869 0.060 Uiso 1 1 calc R . . H4C H 0.4533 -0.0356 0.8654 0.060 Uiso 1 1 calc R . . C5 C 0.1585(5) 0.4591(3) 0.8792(3) 0.0291(8) Uani 1 1 d . . . H5A H 0.2005 0.5236 0.9087 0.044 Uiso 1 1 calc R . . H5B H 0.0613 0.4386 0.9240 0.044 Uiso 1 1 calc R . . H5C H 0.1073 0.4838 0.8124 0.044 Uiso 1 1 calc R . . C6 C 0.4949(5) 0.4769(3) 0.7826(3) 0.0230(7) Uani 1 1 d . . . C7 C 0.5746(5) 0.5567(3) 0.8313(3) 0.0255(7) Uani 1 1 d . . . C8 C 0.5857(5) 0.6608(3) 0.7851(3) 0.0334(9) Uani 1 1 d . . . C9 C 0.5186(6) 0.6894(3) 0.6901(4) 0.0394(10) Uani 1 1 d . . . C10 C 0.4410(6) 0.6130(4) 0.6391(3) 0.0380(10) Uani 1 1 d . . . C11 C 0.4310(5) 0.5074(3) 0.6863(3) 0.0323(9) Uani 1 1 d . . . C12 C 0.6778(4) 0.0613(3) 0.7377(3) 0.0232(7) Uani 1 1 d . . . C13 C 0.8223(5) -0.0309(3) 0.7699(3) 0.0316(9) Uani 1 1 d . . . C14 C 0.9312(6) -0.1091(4) 0.7016(4) 0.0418(10) Uani 1 1 d . . . C15 C 0.8964(6) -0.0958(4) 0.6001(3) 0.0405(10) Uani 1 1 d . . . C16 C 0.7495(6) -0.0057(3) 0.5660(3) 0.0363(9) Uani 1 1 d . . . C17 C 0.6443(5) 0.0707(3) 0.6348(3) 0.0285(8) Uani 1 1 d . . . B1 B 0.6513(5) 0.2582(3) 0.8261(3) 0.0207(8) Uani 1 1 d . . . N1 N 0.4845(4) 0.3665(2) 0.8280(2) 0.0209(6) Uani 1 1 d . . . N2 N 0.5783(4) 0.1507(2) 0.8047(2) 0.0220(6) Uani 1 1 d . . . F1 F 0.6448(3) 0.53000(19) 0.92284(17) 0.0350(5) Uani 1 1 d . . . F2 F 0.6673(4) 0.7347(2) 0.8321(2) 0.0498(7) Uani 1 1 d . . . F3 F 0.5297(4) 0.7920(2) 0.6454(2) 0.0571(8) Uani 1 1 d . . . F4 F 0.3796(4) 0.6387(3) 0.5458(2) 0.0592(8) Uani 1 1 d . . . F5 F 0.3573(4) 0.4316(2) 0.63747(18) 0.0448(6) Uani 1 1 d . . . F6 F 0.8570(4) -0.0450(2) 0.86852(19) 0.0489(7) Uani 1 1 d . . . F7 F 1.0692(4) -0.1971(3) 0.7352(2) 0.0700(9) Uani 1 1 d . . . F8 F 1.0040(4) -0.1692(2) 0.5331(2) 0.0624(8) Uani 1 1 d . . . F9 F 0.7182(4) 0.0063(2) 0.46602(19) 0.0540(7) Uani 1 1 d . . . F10 F 0.5085(4) 0.1598(2) 0.60002(19) 0.0433(6) Uani 1 1 d . . . I1 I 0.87958(3) 0.27983(2) 0.717416(18) 0.02664(9) Uani 1 1 d . . . I2 I 0.77175(3) 0.231036(19) 0.989046(17) 0.02499(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0194(16) 0.0267(18) 0.0245(18) -0.0053(14) -0.0022(14) -0.0061(14) C2 0.0205(16) 0.0326(19) 0.0277(19) -0.0016(15) 0.0011(15) -0.0091(14) C3 0.0242(17) 0.0256(18) 0.029(2) 0.0022(15) -0.0032(15) -0.0116(14) C4 0.035(2) 0.028(2) 0.061(3) -0.0004(19) 0.002(2) -0.0178(17) C5 0.0195(17) 0.0284(19) 0.037(2) -0.0068(16) -0.0008(16) -0.0010(14) C6 0.0204(16) 0.0239(17) 0.0246(18) 0.0006(14) 0.0016(14) -0.0055(13) C7 0.0232(17) 0.0231(17) 0.0298(19) -0.0024(15) 0.0023(15) -0.0052(14) C8 0.0311(19) 0.0227(18) 0.048(2) -0.0038(17) 0.0032(18) -0.0091(15) C9 0.038(2) 0.027(2) 0.052(3) 0.0112(19) 0.004(2) -0.0057(17) C10 0.039(2) 0.039(2) 0.032(2) 0.0097(18) -0.0045(18) -0.0025(18) C11 0.0316(19) 0.0294(19) 0.036(2) -0.0016(17) -0.0019(17) -0.0067(15) C12 0.0211(16) 0.0188(16) 0.0304(19) -0.0027(14) -0.0004(14) -0.0058(13) C13 0.036(2) 0.0240(18) 0.033(2) -0.0026(15) -0.0060(17) -0.0024(15) C14 0.034(2) 0.033(2) 0.053(3) -0.0079(19) -0.005(2) 0.0041(17) C15 0.051(3) 0.029(2) 0.041(2) -0.0159(18) 0.012(2) -0.0096(19) C16 0.054(3) 0.030(2) 0.029(2) -0.0030(16) -0.0006(19) -0.0187(18) C17 0.037(2) 0.0205(17) 0.0290(19) 0.0004(14) -0.0069(16) -0.0077(15) B1 0.0199(17) 0.0209(18) 0.0214(19) -0.0006(15) -0.0001(15) -0.0053(14) N1 0.0201(13) 0.0185(13) 0.0249(15) -0.0019(11) 0.0001(12) -0.0064(11) N2 0.0201(13) 0.0193(14) 0.0266(16) 0.0002(12) -0.0027(12) -0.0048(11) F1 0.0418(13) 0.0329(12) 0.0337(13) -0.0019(9) -0.0089(10) -0.0139(10) F2 0.0622(16) 0.0342(13) 0.0616(18) -0.0035(12) 0.0012(14) -0.0287(12) F3 0.0691(18) 0.0341(14) 0.0681(19) 0.0230(13) 0.0014(15) -0.0157(12) F4 0.075(2) 0.0603(18) 0.0399(15) 0.0240(13) -0.0155(14) -0.0133(15) F5 0.0622(16) 0.0428(14) 0.0334(14) 0.0010(11) -0.0190(12) -0.0180(12) F6 0.0595(16) 0.0396(13) 0.0367(14) -0.0026(11) -0.0173(12) 0.0113(12) F7 0.0637(18) 0.0521(17) 0.072(2) -0.0149(15) -0.0138(16) 0.0319(14) F8 0.0731(19) 0.0496(16) 0.0583(19) -0.0252(14) 0.0235(15) -0.0052(14) F9 0.088(2) 0.0480(15) 0.0281(13) -0.0091(11) -0.0038(13) -0.0206(14) F10 0.0577(15) 0.0315(12) 0.0386(14) -0.0003(10) -0.0201(12) -0.0039(11) I1 0.02283(14) 0.02987(15) 0.02861(16) -0.00439(10) 0.00526(10) -0.00973(10) I2 0.02260(14) 0.02883(15) 0.02398(15) 0.00125(10) -0.00370(10) -0.00686(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.337(5) . ? C1 C2 1.391(5) . ? C1 C5 1.494(5) . ? C2 C3 1.388(5) . ? C2 H2 0.9500 . ? C3 N2 1.340(5) . ? C3 C4 1.501(5) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C11 1.380(5) . ? C6 C7 1.401(5) . ? C6 N1 1.428(4) . ? C7 F1 1.331(4) . ? C7 C8 1.368(5) . ? C8 F2 1.345(5) . ? C8 C9 1.368(6) . ? C9 F3 1.343(5) . ? C9 C10 1.378(6) . ? C10 F4 1.329(5) . ? C10 C11 1.386(6) . ? C11 F5 1.339(5) . ? C12 C17 1.385(5) . ? C12 C13 1.388(5) . ? C12 N2 1.424(4) . ? C13 F6 1.333(4) . ? C13 C14 1.383(6) . ? C14 F7 1.339(4) . ? C14 C15 1.369(6) . ? C15 F8 1.340(5) . ? C15 C16 1.392(6) . ? C16 F9 1.345(5) . ? C16 C17 1.365(6) . ? C17 F10 1.342(4) . ? B1 N2 1.523(5) . ? B1 N1 1.533(4) . ? B1 I1 2.222(4) . ? B1 I2 2.342(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 119.8(3) . . ? N1 C1 C5 120.2(3) . . ? C2 C1 C5 119.9(3) . . ? C3 C2 C1 120.5(4) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? N2 C3 C2 119.3(3) . . ? N2 C3 C4 119.9(3) . . ? C2 C3 C4 120.6(3) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C1 C5 H5A 109.5 . . ? C1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C11 C6 C7 117.2(3) . . ? C11 C6 N1 120.5(3) . . ? C7 C6 N1 122.3(3) . . ? F1 C7 C8 119.2(3) . . ? F1 C7 C6 119.9(3) . . ? C8 C7 C6 120.9(3) . . ? F2 C8 C9 119.5(3) . . ? F2 C8 C7 120.0(4) . . ? C9 C8 C7 120.5(4) . . ? F3 C9 C8 120.1(4) . . ? F3 C9 C10 119.5(4) . . ? C8 C9 C10 120.4(4) . . ? F4 C10 C9 120.8(4) . . ? F4 C10 C11 120.4(4) . . ? C9 C10 C11 118.7(4) . . ? F5 C11 C6 118.3(3) . . ? F5 C11 C10 119.5(3) . . ? C6 C11 C10 122.2(4) . . ? C17 C12 C13 117.5(3) . . ? C17 C12 N2 120.0(3) . . ? C13 C12 N2 122.2(3) . . ? F6 C13 C14 119.1(3) . . ? F6 C13 C12 119.6(3) . . ? C14 C13 C12 121.3(4) . . ? F7 C14 C15 120.6(4) . . ? F7 C14 C13 119.8(4) . . ? C15 C14 C13 119.7(4) . . ? F8 C15 C14 120.1(4) . . ? F8 C15 C16 119.6(4) . . ? C14 C15 C16 120.2(4) . . ? F9 C16 C17 121.5(3) . . ? F9 C16 C15 119.4(4) . . ? C17 C16 C15 119.1(4) . . ? F10 C17 C16 118.2(3) . . ? F10 C17 C12 119.5(3) . . ? C16 C17 C12 122.2(3) . . ? N2 B1 N1 108.1(3) . . ? N2 B1 I1 113.0(2) . . ? N1 B1 I1 112.6(2) . . ? N2 B1 I2 107.0(2) . . ? N1 B1 I2 107.9(2) . . ? I1 B1 I2 108.04(15) . . ? C1 N1 C6 119.1(3) . . ? C1 N1 B1 118.3(3) . . ? C6 N1 B1 122.4(3) . . ? C3 N2 C12 120.0(3) . . ? C3 N2 B1 118.5(3) . . ? C12 N2 B1 121.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -20.6(5) . . . . ? C5 C1 C2 C3 155.2(3) . . . . ? C1 C2 C3 N2 18.3(5) . . . . ? C1 C2 C3 C4 -157.8(4) . . . . ? C11 C6 C7 F1 -177.5(3) . . . . ? N1 C6 C7 F1 0.4(5) . . . . ? C11 C6 C7 C8 0.8(5) . . . . ? N1 C6 C7 C8 178.7(3) . . . . ? F1 C7 C8 F2 0.1(5) . . . . ? C6 C7 C8 F2 -178.2(3) . . . . ? F1 C7 C8 C9 178.5(3) . . . . ? C6 C7 C8 C9 0.2(6) . . . . ? F2 C8 C9 F3 -1.8(6) . . . . ? C7 C8 C9 F3 179.8(4) . . . . ? F2 C8 C9 C10 177.5(4) . . . . ? C7 C8 C9 C10 -0.9(6) . . . . ? F3 C9 C10 F4 1.0(6) . . . . ? C8 C9 C10 F4 -178.3(4) . . . . ? F3 C9 C10 C11 179.9(4) . . . . ? C8 C9 C10 C11 0.6(6) . . . . ? C7 C6 C11 F5 178.9(3) . . . . ? N1 C6 C11 F5 0.9(5) . . . . ? C7 C6 C11 C10 -1.1(6) . . . . ? N1 C6 C11 C10 -179.1(4) . . . . ? F4 C10 C11 F5 -0.6(6) . . . . ? C9 C10 C11 F5 -179.5(4) . . . . ? F4 C10 C11 C6 179.4(4) . . . . ? C9 C10 C11 C6 0.5(6) . . . . ? C17 C12 C13 F6 -178.5(3) . . . . ? N2 C12 C13 F6 7.7(6) . . . . ? C17 C12 C13 C14 1.2(6) . . . . ? N2 C12 C13 C14 -172.5(4) . . . . ? F6 C13 C14 F7 -0.1(6) . . . . ? C12 C13 C14 F7 -179.9(4) . . . . ? F6 C13 C14 C15 179.7(4) . . . . ? C12 C13 C14 C15 -0.1(7) . . . . ? F7 C14 C15 F8 -1.9(7) . . . . ? C13 C14 C15 F8 178.3(4) . . . . ? F7 C14 C15 C16 178.4(4) . . . . ? C13 C14 C15 C16 -1.4(7) . . . . ? F8 C15 C16 F9 -0.1(6) . . . . ? C14 C15 C16 F9 179.6(4) . . . . ? F8 C15 C16 C17 -178.1(4) . . . . ? C14 C15 C16 C17 1.7(7) . . . . ? F9 C16 C17 F10 -0.6(6) . . . . ? C15 C16 C17 F10 177.2(4) . . . . ? F9 C16 C17 C12 -178.3(3) . . . . ? C15 C16 C17 C12 -0.4(6) . . . . ? C13 C12 C17 F10 -178.6(3) . . . . ? N2 C12 C17 F10 -4.7(5) . . . . ? C13 C12 C17 C16 -1.0(6) . . . . ? N2 C12 C17 C16 172.9(3) . . . . ? C2 C1 N1 C6 166.2(3) . . . . ? C5 C1 N1 C6 -9.6(5) . . . . ? C2 C1 N1 B1 -9.4(5) . . . . ? C5 C1 N1 B1 174.8(3) . . . . ? C11 C6 N1 C1 -78.2(4) . . . . ? C7 C6 N1 C1 103.9(4) . . . . ? C11 C6 N1 B1 97.2(4) . . . . ? C7 C6 N1 B1 -80.7(4) . . . . ? N2 B1 N1 C1 36.7(4) . . . . ? I1 B1 N1 C1 162.1(2) . . . . ? I2 B1 N1 C1 -78.7(3) . . . . ? N2 B1 N1 C6 -138.7(3) . . . . ? I1 B1 N1 C6 -13.3(4) . . . . ? I2 B1 N1 C6 105.8(3) . . . . ? C2 C3 N2 C12 -164.2(3) . . . . ? C4 C3 N2 C12 12.0(5) . . . . ? C2 C3 N2 B1 13.8(5) . . . . ? C4 C3 N2 B1 -170.0(3) . . . . ? C17 C12 N2 C3 89.2(4) . . . . ? C13 C12 N2 C3 -97.2(4) . . . . ? C17 C12 N2 B1 -88.7(4) . . . . ? C13 C12 N2 B1 84.9(4) . . . . ? N1 B1 N2 C3 -39.0(4) . . . . ? I1 B1 N2 C3 -164.2(2) . . . . ? I2 B1 N2 C3 77.0(3) . . . . ? N1 B1 N2 C12 138.9(3) . . . . ? I1 B1 N2 C12 13.7(4) . . . . ? I2 B1 N2 C12 -105.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.721 _refine_diff_density_min -1.286 _refine_diff_density_rms 0.258 # Attachment 'Compound131.cif' data_compound8_Compound131 _database_code_depnum_ccdc_archive 'CCDC 670305' _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H7 B Cl F10 N2, Al Cl4' _chemical_formula_sum 'C17 H7 Al B Cl5 F10 N2' _chemical_formula_weight 644.29 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Al Al 0.0645 0.0514 '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 12.270(3) _cell_length_b 14.185(3) _cell_length_c 14.556(3) _cell_angle_alpha 89.71(3) _cell_angle_beta 81.36(3) _cell_angle_gamma 77.91(3) _cell_volume 2448.0(8) _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 plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.748 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.716 _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 153(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 '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 13783 _diffrn_reflns_av_R_equivalents 0.0472 _diffrn_reflns_av_sigmaI/netI 0.1747 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 26.02 _reflns_number_total 9534 _reflns_number_gt 3771 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _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^)+(0.1092P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef none _refine_ls_number_reflns 9534 _refine_ls_number_parameters 653 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1999 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.2233 _refine_ls_wR_factor_gt 0.1374 _refine_ls_goodness_of_fit_ref 0.936 _refine_ls_restrained_S_all 0.936 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8997(5) 0.6862(4) 0.3496(5) 0.0444(16) Uani 1 1 d . . . C2 C 0.8649(5) 0.6511(4) 0.2724(5) 0.0462(17) Uani 1 1 d . . . H2 H 0.8177 0.6074 0.2820 0.055 Uiso 1 1 calc R . . C3 C 0.8960(5) 0.6770(4) 0.1830(4) 0.0406(16) Uani 1 1 d . . . C4 C 0.8681(6) 0.6542(5) 0.4458(4) 0.060(2) Uani 1 1 d . . . H4A H 0.9346 0.6359 0.4746 0.090 Uiso 1 1 calc R . . H4B H 0.8330 0.6000 0.4434 0.090 Uiso 1 1 calc R . . H4C H 0.8163 0.7061 0.4814 0.090 Uiso 1 1 calc R . . C5 C 0.8574(6) 0.6369(5) 0.1033(5) 0.0524(18) Uani 1 1 d . . . H5A H 0.8172 0.6885 0.0706 0.079 Uiso 1 1 calc R . . H5B H 0.8084 0.5943 0.1253 0.079 Uiso 1 1 calc R . . H5C H 0.9214 0.6017 0.0621 0.079 Uiso 1 1 calc R . . C6 C 1.0029(6) 0.7914(5) 0.4130(5) 0.0474(17) Uani 1 1 d . . . C7 C 0.9344(7) 0.8619(5) 0.4730(5) 0.0557(19) Uani 1 1 d . . . C8 C 0.9720(9) 0.9013(6) 0.5440(6) 0.067(2) Uani 1 1 d . . . C9 C 1.0811(10) 0.8711(7) 0.5578(6) 0.075(3) Uani 1 1 d . . . C10 C 1.1540(8) 0.8014(7) 0.4993(6) 0.073(3) Uani 1 1 d . . . C11 C 1.1127(7) 0.7619(5) 0.4295(5) 0.060(2) Uani 1 1 d . . . C12 C 1.0022(5) 0.7670(4) 0.0738(4) 0.0431(16) Uani 1 1 d . . . C13 C 0.9457(6) 0.8455(5) 0.0333(5) 0.0568(19) Uani 1 1 d . . . C14 C 0.9857(7) 0.8722(6) -0.0541(5) 0.070(2) Uani 1 1 d . . . C15 C 1.0842(7) 0.8196(6) -0.1009(5) 0.061(2) Uani 1 1 d . . . C16 C 1.1423(6) 0.7423(6) -0.0597(5) 0.064(2) Uani 1 1 d . . . C17 C 1.1001(6) 0.7160(5) 0.0265(5) 0.0559(19) Uani 1 1 d . . . C18 C 0.4015(5) 0.1727(4) 0.1710(4) 0.0428(16) Uani 1 1 d . . . C19 C 0.3626(6) 0.2612(4) 0.1352(4) 0.0484(17) Uani 1 1 d . . . H19 H 0.3226 0.2639 0.0855 0.058 Uiso 1 1 calc R . . C20 C 0.3806(5) 0.3478(4) 0.1705(4) 0.0441(16) Uani 1 1 d . . . C21 C 0.3762(6) 0.0829(4) 0.1368(5) 0.060(2) Uani 1 1 d . . . H21A H 0.4455 0.0376 0.1160 0.089 Uiso 1 1 calc R . . H21B H 0.3342 0.0970 0.0861 0.089 Uiso 1 1 calc R . . H21C H 0.3325 0.0556 0.1862 0.089 Uiso 1 1 calc R . . C22 C 0.3317(6) 0.4426(4) 0.1315(5) 0.0518(18) Uani 1 1 d . . . H22A H 0.2894 0.4855 0.1812 0.078 Uiso 1 1 calc R . . H22B H 0.2829 0.4328 0.0884 0.078 Uiso 1 1 calc R . . H22C H 0.3916 0.4703 0.1000 0.078 Uiso 1 1 calc R . . C23 C 0.5046(5) 0.0759(4) 0.2811(4) 0.0390(15) Uani 1 1 d . . . C24 C 0.4358(6) 0.0418(4) 0.3512(5) 0.0494(17) Uani 1 1 d . . . C25 C 0.4737(6) -0.0415(5) 0.3946(5) 0.0515(19) Uani 1 1 d . . . C26 C 0.5826(7) -0.0931(4) 0.3672(5) 0.0507(18) Uani 1 1 d . . . C27 C 0.6520(6) -0.0600(4) 0.2990(4) 0.0455(16) Uani 1 1 d . . . C28 C 0.6131(6) 0.0252(4) 0.2568(4) 0.0458(17) Uani 1 1 d . . . C29 C 0.4577(6) 0.4303(4) 0.2827(5) 0.0433(16) Uani 1 1 d . . . C30 C 0.4009(5) 0.4599(4) 0.3704(5) 0.0447(17) Uani 1 1 d . . . C31 C 0.4172(6) 0.5386(5) 0.4156(5) 0.0533(18) Uani 1 1 d . . . C32 C 0.4913(7) 0.5910(5) 0.3707(6) 0.059(2) Uani 1 1 d . . . C33 C 0.5490(6) 0.5642(5) 0.2849(5) 0.0543(19) Uani 1 1 d . . . C34 C 0.5334(5) 0.4830(4) 0.2404(5) 0.0451(17) Uani 1 1 d . . . B1 B 0.9973(6) 0.7862(5) 0.2438(5) 0.0454(19) Uani 1 1 d . . . B2 B 0.4924(7) 0.2523(5) 0.2774(5) 0.0443(19) Uani 1 1 d . . . N1 N 0.9645(4) 0.7540(3) 0.3352(3) 0.0412(13) Uani 1 1 d . . . N2 N 0.9635(4) 0.7425(3) 0.1684(3) 0.0386(12) Uani 1 1 d . . . N3 N 0.4658(4) 0.1679(3) 0.2407(3) 0.0407(13) Uani 1 1 d . . . N4 N 0.4438(4) 0.3430(3) 0.2394(4) 0.0420(13) Uani 1 1 d . . . F1 F 0.8264(4) 0.8947(3) 0.4580(3) 0.0674(11) Uani 1 1 d . . . F2 F 0.9022(5) 0.9694(3) 0.6016(3) 0.0892(15) Uani 1 1 d . . . F3 F 1.1202(5) 0.9105(3) 0.6259(3) 0.111(2) Uani 1 1 d . . . F4 F 1.2611(5) 0.7729(3) 0.5097(4) 0.1034(18) Uani 1 1 d . . . F5 F 1.1826(4) 0.6930(3) 0.3725(3) 0.0723(12) Uani 1 1 d . . . F6 F 0.8502(4) 0.8989(3) 0.0793(3) 0.0986(17) Uani 1 1 d . . . F7 F 0.9283(5) 0.9488(4) -0.0929(3) 0.121(2) Uani 1 1 d . . . F8 F 1.1233(4) 0.8457(3) -0.1866(3) 0.0880(14) Uani 1 1 d . . . F9 F 1.2377(4) 0.6913(4) -0.1069(3) 0.1132(18) Uani 1 1 d . . . F10 F 1.1562(4) 0.6390(3) 0.0644(3) 0.1001(17) Uani 1 1 d . . . F11 F 0.3306(3) 0.0919(3) 0.3767(3) 0.0698(12) Uani 1 1 d . . . F12 F 0.4057(4) -0.0750(3) 0.4619(3) 0.0737(12) Uani 1 1 d . . . F13 F 0.6207(4) -0.1750(2) 0.4101(3) 0.0683(12) Uani 1 1 d . . . F14 F 0.7579(4) -0.1094(3) 0.2740(3) 0.0692(11) Uani 1 1 d . . . F15 F 0.6837(3) 0.0570(3) 0.1897(3) 0.0610(11) Uani 1 1 d . . . F16 F 0.3332(3) 0.4054(3) 0.4154(3) 0.0615(11) Uani 1 1 d . . . F17 F 0.3623(4) 0.5643(3) 0.5010(3) 0.0788(13) Uani 1 1 d . . . F18 F 0.5095(4) 0.6676(3) 0.4155(3) 0.0840(14) Uani 1 1 d . . . F19 F 0.6227(3) 0.6144(3) 0.2435(3) 0.0748(13) Uani 1 1 d . . . F20 F 0.5910(3) 0.4556(3) 0.1568(3) 0.0639(11) Uani 1 1 d . . . Al1 Al 0.44119(19) 0.79348(14) 0.11360(14) 0.0538(6) Uani 1 1 d . . . Cl1 Cl 1.07701(16) 0.87506(13) 0.22697(12) 0.0619(5) Uani 1 1 d . . . Cl2 Cl 0.57705(17) 0.24584(11) 0.36248(14) 0.0689(6) Uani 1 1 d . . . Cl3 Cl 0.60201(16) 0.83347(12) 0.10269(13) 0.0613(5) Uani 1 1 d . . . Cl4 Cl 0.34120(18) 0.87965(13) 0.02444(14) 0.0728(6) Uani 1 1 d . . . Cl5 Cl 0.36724(18) 0.81497(16) 0.25522(14) 0.0797(6) Uani 1 1 d . . . Cl6 Cl 0.4645(2) 0.64730(12) 0.06915(15) 0.0830(7) Uani 1 1 d . . . Al2 Al 0.0293(2) 0.38057(15) 0.27934(16) 0.0652(7) Uani 1 1 d . . . Cl7 Cl 0.10561(19) 0.48495(18) 0.33464(15) 0.0902(7) Uani 1 1 d . . . Cl8 Cl 0.0306(2) 0.40503(15) 0.13522(14) 0.0789(6) Uani 1 1 d . . . Cl9 Cl -0.13799(19) 0.39550(15) 0.34834(19) 0.0994(9) Uani 1 1 d . . . Cl10 Cl 0.1250(2) 0.24115(17) 0.2976(2) 0.1347(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.041(4) 0.049(4) 0.045(4) 0.010(3) -0.012(3) -0.008(3) C2 0.041(4) 0.048(4) 0.051(5) 0.008(3) -0.005(3) -0.012(3) C3 0.035(4) 0.038(3) 0.045(4) 0.004(3) -0.004(3) -0.001(3) C4 0.076(5) 0.063(4) 0.046(4) 0.012(4) -0.004(4) -0.027(4) C5 0.057(5) 0.054(4) 0.047(4) 0.001(3) -0.011(4) -0.013(4) C6 0.045(5) 0.053(4) 0.049(5) 0.020(4) -0.013(4) -0.016(4) C7 0.067(6) 0.063(5) 0.044(5) 0.016(4) -0.014(4) -0.029(5) C8 0.097(7) 0.055(5) 0.055(6) 0.008(4) -0.013(6) -0.028(5) C9 0.123(9) 0.069(6) 0.055(6) 0.025(5) -0.041(6) -0.050(6) C10 0.088(7) 0.080(6) 0.081(7) 0.041(5) -0.061(6) -0.053(6) C11 0.075(6) 0.052(5) 0.064(5) 0.028(4) -0.028(5) -0.028(5) C12 0.040(4) 0.050(4) 0.038(4) 0.004(3) -0.002(3) -0.011(3) C13 0.054(5) 0.058(4) 0.048(5) 0.010(4) 0.003(4) 0.005(4) C14 0.076(6) 0.071(5) 0.056(5) 0.032(4) -0.004(5) -0.008(5) C15 0.065(6) 0.070(5) 0.050(5) 0.008(4) 0.010(4) -0.029(5) C16 0.046(5) 0.080(5) 0.058(5) -0.013(5) 0.004(4) -0.001(4) C17 0.054(5) 0.064(5) 0.040(5) 0.004(4) 0.003(4) 0.000(4) C18 0.040(4) 0.046(4) 0.045(4) 0.003(3) -0.013(3) -0.008(3) C19 0.067(5) 0.045(4) 0.039(4) 0.010(3) -0.022(4) -0.014(4) C20 0.046(4) 0.043(4) 0.043(4) 0.007(3) -0.007(4) -0.012(3) C21 0.082(6) 0.040(4) 0.065(5) 0.002(3) -0.032(4) -0.019(4) C22 0.057(5) 0.044(4) 0.056(5) 0.011(3) -0.019(4) -0.007(3) C23 0.045(4) 0.035(3) 0.036(4) 0.006(3) -0.010(3) -0.004(3) C24 0.048(5) 0.044(4) 0.055(5) 0.007(3) -0.013(4) -0.002(4) C25 0.062(5) 0.052(4) 0.047(4) 0.018(4) -0.017(4) -0.022(4) C26 0.071(6) 0.031(4) 0.057(5) 0.012(3) -0.029(4) -0.013(4) C27 0.047(5) 0.043(4) 0.044(4) 0.002(3) -0.014(4) 0.000(4) C28 0.056(5) 0.043(4) 0.039(4) 0.006(3) -0.009(4) -0.010(4) C29 0.047(4) 0.035(3) 0.047(5) 0.006(3) -0.013(4) -0.003(3) C30 0.038(4) 0.040(4) 0.056(5) 0.008(3) -0.012(4) -0.007(3) C31 0.068(5) 0.045(4) 0.046(5) 0.000(4) -0.011(4) -0.007(4) C32 0.077(6) 0.041(4) 0.066(6) -0.003(4) -0.032(5) -0.013(4) C33 0.058(5) 0.042(4) 0.068(6) 0.001(4) -0.012(4) -0.020(4) C34 0.040(4) 0.046(4) 0.045(4) 0.005(3) -0.004(4) -0.004(3) B1 0.041(5) 0.049(4) 0.048(5) 0.008(4) -0.010(4) -0.009(4) B2 0.046(5) 0.039(4) 0.048(5) 0.008(4) -0.015(4) -0.004(4) N1 0.041(3) 0.044(3) 0.043(3) 0.011(2) -0.016(3) -0.013(3) N2 0.037(3) 0.041(3) 0.036(3) 0.008(2) -0.001(3) -0.006(3) N3 0.049(3) 0.031(3) 0.044(3) 0.006(2) -0.014(3) -0.007(2) N4 0.047(3) 0.030(3) 0.051(3) 0.002(2) -0.013(3) -0.008(2) F1 0.071(3) 0.073(3) 0.058(3) -0.004(2) -0.002(2) -0.019(2) F2 0.139(5) 0.083(3) 0.056(3) -0.003(3) -0.007(3) -0.052(3) F3 0.193(6) 0.106(4) 0.076(3) 0.030(3) -0.074(4) -0.091(4) F4 0.114(4) 0.102(4) 0.131(4) 0.053(3) -0.088(4) -0.058(3) F5 0.057(3) 0.069(3) 0.098(4) 0.026(3) -0.034(3) -0.014(2) F6 0.088(4) 0.093(3) 0.077(3) 0.041(3) 0.025(3) 0.039(3) F7 0.133(5) 0.109(4) 0.086(4) 0.062(3) 0.022(3) 0.028(3) F8 0.101(4) 0.114(4) 0.051(3) 0.014(2) 0.012(3) -0.043(3) F9 0.083(4) 0.145(5) 0.077(4) 0.000(3) 0.031(3) 0.025(3) F10 0.084(3) 0.097(3) 0.084(3) 0.022(3) 0.004(3) 0.047(3) F11 0.052(3) 0.081(3) 0.066(3) 0.022(2) 0.002(2) 0.000(2) F12 0.079(3) 0.079(3) 0.069(3) 0.034(2) -0.014(2) -0.028(2) F13 0.088(3) 0.044(2) 0.080(3) 0.023(2) -0.038(2) -0.014(2) F14 0.065(3) 0.067(2) 0.064(3) 0.007(2) -0.012(2) 0.014(2) F15 0.055(3) 0.066(2) 0.057(3) 0.017(2) -0.004(2) -0.006(2) F16 0.068(3) 0.063(2) 0.055(3) 0.0143(19) -0.004(2) -0.022(2) F17 0.105(4) 0.069(3) 0.055(3) -0.008(2) -0.002(3) -0.009(3) F18 0.119(4) 0.060(3) 0.086(3) -0.006(2) -0.035(3) -0.034(3) F19 0.069(3) 0.067(3) 0.099(3) 0.014(2) -0.015(3) -0.035(2) F20 0.062(3) 0.056(2) 0.067(3) 0.005(2) 0.009(2) -0.008(2) Al1 0.0682(15) 0.0464(11) 0.0507(13) 0.0072(10) -0.0140(12) -0.0175(11) Cl1 0.0740(13) 0.0669(11) 0.0560(11) 0.0180(9) -0.0162(10) -0.0359(10) Cl2 0.0906(16) 0.0446(10) 0.0806(14) 0.0032(9) -0.0529(12) -0.0064(10) Cl3 0.0665(13) 0.0616(11) 0.0589(12) -0.0009(9) -0.0115(10) -0.0191(10) Cl4 0.0921(16) 0.0596(11) 0.0756(14) 0.0106(10) -0.0389(12) -0.0177(11) Cl5 0.0750(15) 0.1140(16) 0.0529(13) 0.0012(11) -0.0050(11) -0.0297(13) Cl6 0.133(2) 0.0477(10) 0.0781(15) 0.0097(10) -0.0265(14) -0.0338(12) Al2 0.0673(16) 0.0610(13) 0.0585(15) 0.0191(11) 0.0023(12) -0.0027(12) Cl7 0.0708(15) 0.1297(19) 0.0690(15) -0.0117(13) -0.0259(12) -0.0079(14) Cl8 0.1002(17) 0.0888(14) 0.0541(13) 0.0029(10) -0.0195(12) -0.0286(13) Cl9 0.0798(16) 0.0696(13) 0.130(2) 0.0211(13) 0.0336(15) -0.0087(12) Cl10 0.127(2) 0.0869(16) 0.139(2) 0.0605(16) 0.0546(19) 0.0371(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.366(7) . ? C1 C2 1.390(9) . ? C1 C4 1.491(8) . ? C2 C3 1.370(8) . ? C2 H2 0.9300 . ? C3 N2 1.365(7) . ? C3 C5 1.477(9) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C11 1.381(10) . ? C6 C7 1.380(10) . ? C6 N1 1.435(8) . ? C7 F1 1.359(8) . ? C7 C8 1.361(11) . ? C8 F2 1.347(9) . ? C8 C9 1.362(12) . ? C9 F3 1.337(9) . ? C9 C10 1.382(12) . ? C10 F4 1.322(9) . ? C10 C11 1.372(10) . ? C11 F5 1.350(9) . ? C12 C17 1.353(9) . ? C12 C13 1.364(9) . ? C12 N2 1.453(7) . ? C13 F6 1.339(8) . ? C13 C14 1.374(9) . ? C14 F7 1.337(8) . ? C14 C15 1.364(10) . ? C15 F8 1.346(8) . ? C15 C16 1.365(10) . ? C16 F9 1.332(8) . ? C16 C17 1.366(10) . ? C17 F10 1.328(8) . ? C18 N3 1.369(7) . ? C18 C19 1.375(8) . ? C18 C21 1.479(8) . ? C19 C20 1.405(8) . ? C19 H19 0.9300 . ? C20 N4 1.350(8) . ? C20 C22 1.499(8) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C28 1.369(8) . ? C23 C24 1.376(8) . ? C23 N3 1.446(7) . ? C24 F11 1.335(7) . ? C24 C25 1.364(9) . ? C25 F12 1.340(7) . ? C25 C26 1.384(9) . ? C26 F13 1.345(7) . ? C26 C27 1.357(9) . ? C27 F14 1.338(7) . ? C27 C28 1.380(8) . ? C28 F15 1.346(7) . ? C29 C30 1.380(9) . ? C29 C34 1.383(8) . ? C29 N4 1.446(7) . ? C30 F16 1.348(7) . ? C30 C31 1.364(9) . ? C31 F17 1.334(8) . ? C31 C32 1.381(10) . ? C32 F18 1.345(7) . ? C32 C33 1.354(10) . ? C33 F19 1.339(7) . ? C33 C34 1.386(9) . ? C34 F20 1.328(7) . ? B1 N2 1.418(9) . ? B1 N1 1.432(9) . ? B1 Cl1 1.745(7) . ? B2 N3 1.431(8) . ? B2 N4 1.444(8) . ? B2 Cl2 1.723(8) . ? Al1 Cl5 2.120(3) . ? Al1 Cl6 2.124(3) . ? Al1 Cl4 2.125(3) . ? Al1 Cl3 2.148(3) . ? Al2 Cl9 2.114(3) . ? Al2 Cl10 2.115(3) . ? Al2 Cl8 2.123(3) . ? Al2 Cl7 2.130(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 117.5(5) . . ? N1 C1 C4 119.6(6) . . ? C2 C1 C4 122.9(6) . . ? C3 C2 C1 124.0(6) . . ? C3 C2 H2 118.0 . . ? C1 C2 H2 118.0 . . ? N2 C3 C2 118.4(6) . . ? N2 C3 C5 119.8(5) . . ? C2 C3 C5 121.8(6) . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C11 C6 C7 116.1(7) . . ? C11 C6 N1 121.6(7) . . ? C7 C6 N1 122.2(7) . . ? F1 C7 C8 119.4(8) . . ? F1 C7 C6 118.1(7) . . ? C8 C7 C6 122.5(8) . . ? F2 C8 C7 120.7(9) . . ? F2 C8 C9 119.5(9) . . ? C7 C8 C9 119.8(9) . . ? F3 C9 C8 120.6(10) . . ? F3 C9 C10 119.0(10) . . ? C8 C9 C10 120.3(8) . . ? F4 C10 C11 120.3(10) . . ? F4 C10 C9 121.4(8) . . ? C11 C10 C9 118.3(9) . . ? F5 C11 C10 119.0(8) . . ? F5 C11 C6 118.1(7) . . ? C10 C11 C6 122.9(9) . . ? C17 C12 C13 118.6(6) . . ? C17 C12 N2 120.1(6) . . ? C13 C12 N2 121.1(6) . . ? F6 C13 C12 120.0(6) . . ? F6 C13 C14 118.8(6) . . ? C12 C13 C14 121.2(7) . . ? F7 C14 C15 120.4(7) . . ? F7 C14 C13 120.2(8) . . ? C15 C14 C13 119.4(7) . . ? F8 C15 C14 119.3(7) . . ? F8 C15 C16 121.1(8) . . ? C14 C15 C16 119.6(7) . . ? F9 C16 C17 121.1(7) . . ? F9 C16 C15 118.7(7) . . ? C17 C16 C15 120.1(7) . . ? F10 C17 C12 119.7(6) . . ? F10 C17 C16 119.2(7) . . ? C12 C17 C16 121.1(7) . . ? N3 C18 C19 118.7(5) . . ? N3 C18 C21 118.9(5) . . ? C19 C18 C21 122.3(6) . . ? C18 C19 C20 122.9(6) . . ? C18 C19 H19 118.5 . . ? C20 C19 H19 118.5 . . ? N4 C20 C19 118.2(5) . . ? N4 C20 C22 121.2(5) . . ? C19 C20 C22 120.6(6) . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C28 C23 C24 118.5(5) . . ? C28 C23 N3 121.1(5) . . ? C24 C23 N3 120.2(6) . . ? F11 C24 C25 120.1(6) . . ? F11 C24 C23 118.9(5) . . ? C25 C24 C23 121.0(7) . . ? F12 C25 C24 120.8(7) . . ? F12 C25 C26 119.7(6) . . ? C24 C25 C26 119.6(6) . . ? F13 C26 C27 120.0(7) . . ? F13 C26 C25 119.8(6) . . ? C27 C26 C25 120.2(6) . . ? F14 C27 C26 119.8(6) . . ? F14 C27 C28 120.6(6) . . ? C26 C27 C28 119.6(7) . . ? F15 C28 C23 120.3(5) . . ? F15 C28 C27 118.5(6) . . ? C23 C28 C27 121.1(6) . . ? C30 C29 C34 118.2(6) . . ? C30 C29 N4 120.5(5) . . ? C34 C29 N4 121.2(6) . . ? F16 C30 C31 118.8(6) . . ? F16 C30 C29 118.9(6) . . ? C31 C30 C29 122.1(6) . . ? F17 C31 C30 120.7(6) . . ? F17 C31 C32 121.0(6) . . ? C30 C31 C32 118.3(7) . . ? F18 C32 C33 119.9(7) . . ? F18 C32 C31 118.7(7) . . ? C33 C32 C31 121.3(6) . . ? F19 C33 C32 120.5(6) . . ? F19 C33 C34 119.7(7) . . ? C32 C33 C34 119.8(6) . . ? F20 C34 C29 119.8(6) . . ? F20 C34 C33 120.0(6) . . ? C29 C34 C33 120.2(7) . . ? N2 B1 N1 117.4(6) . . ? N2 B1 Cl1 121.9(5) . . ? N1 B1 Cl1 120.7(5) . . ? N3 B2 N4 116.3(6) . . ? N3 B2 Cl2 121.7(5) . . ? N4 B2 Cl2 122.0(5) . . ? C1 N1 B1 121.3(5) . . ? C1 N1 C6 119.2(5) . . ? B1 N1 C6 119.4(5) . . ? C3 N2 B1 121.2(5) . . ? C3 N2 C12 119.2(5) . . ? B1 N2 C12 119.6(5) . . ? C18 N3 B2 121.7(5) . . ? C18 N3 C23 119.6(5) . . ? B2 N3 C23 118.7(5) . . ? C20 N4 B2 122.1(5) . . ? C20 N4 C29 120.3(5) . . ? B2 N4 C29 117.5(5) . . ? Cl5 Al1 Cl6 111.62(12) . . ? Cl5 Al1 Cl4 112.07(14) . . ? Cl6 Al1 Cl4 107.63(12) . . ? Cl5 Al1 Cl3 106.43(12) . . ? Cl6 Al1 Cl3 109.61(13) . . ? Cl4 Al1 Cl3 109.47(11) . . ? Cl9 Al2 Cl10 110.59(13) . . ? Cl9 Al2 Cl8 110.41(15) . . ? Cl10 Al2 Cl8 109.46(15) . . ? Cl9 Al2 Cl7 109.37(14) . . ? Cl10 Al2 Cl7 109.00(16) . . ? Cl8 Al2 Cl7 107.97(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 3.1(10) . . . . ? C4 C1 C2 C3 -177.7(6) . . . . ? C1 C2 C3 N2 -1.3(10) . . . . ? C1 C2 C3 C5 179.5(6) . . . . ? C11 C6 C7 F1 178.5(5) . . . . ? N1 C6 C7 F1 1.4(9) . . . . ? C11 C6 C7 C8 0.6(9) . . . . ? N1 C6 C7 C8 -176.6(6) . . . . ? F1 C7 C8 F2 2.6(10) . . . . ? C6 C7 C8 F2 -179.4(6) . . . . ? F1 C7 C8 C9 -177.9(6) . . . . ? C6 C7 C8 C9 0.0(10) . . . . ? F2 C8 C9 F3 -2.1(10) . . . . ? C7 C8 C9 F3 178.5(6) . . . . ? F2 C8 C9 C10 -179.9(6) . . . . ? C7 C8 C9 C10 0.6(11) . . . . ? F3 C9 C10 F4 0.2(10) . . . . ? C8 C9 C10 F4 178.1(6) . . . . ? F3 C9 C10 C11 -179.7(6) . . . . ? C8 C9 C10 C11 -1.9(11) . . . . ? F4 C10 C11 F5 0.8(9) . . . . ? C9 C10 C11 F5 -179.3(6) . . . . ? F4 C10 C11 C6 -177.4(6) . . . . ? C9 C10 C11 C6 2.6(10) . . . . ? C7 C6 C11 F5 179.9(5) . . . . ? N1 C6 C11 F5 -2.9(9) . . . . ? C7 C6 C11 C10 -1.9(9) . . . . ? N1 C6 C11 C10 175.3(6) . . . . ? C17 C12 C13 F6 -178.2(6) . . . . ? N2 C12 C13 F6 -3.0(10) . . . . ? C17 C12 C13 C14 0.9(11) . . . . ? N2 C12 C13 C14 176.1(7) . . . . ? F6 C13 C14 F7 -1.7(12) . . . . ? C12 C13 C14 F7 179.2(7) . . . . ? F6 C13 C14 C15 178.6(7) . . . . ? C12 C13 C14 C15 -0.5(12) . . . . ? F7 C14 C15 F8 0.2(11) . . . . ? C13 C14 C15 F8 179.9(7) . . . . ? F7 C14 C15 C16 179.3(7) . . . . ? C13 C14 C15 C16 -1.0(12) . . . . ? F8 C15 C16 F9 -1.6(11) . . . . ? C14 C15 C16 F9 179.3(7) . . . . ? F8 C15 C16 C17 -178.8(7) . . . . ? C14 C15 C16 C17 2.1(12) . . . . ? C13 C12 C17 F10 -179.7(6) . . . . ? N2 C12 C17 F10 5.1(10) . . . . ? C13 C12 C17 C16 0.3(10) . . . . ? N2 C12 C17 C16 -175.0(6) . . . . ? F9 C16 C17 F10 1.0(11) . . . . ? C15 C16 C17 F10 178.1(7) . . . . ? F9 C16 C17 C12 -178.9(7) . . . . ? C15 C16 C17 C12 -1.8(11) . . . . ? N3 C18 C19 C20 -3.6(10) . . . . ? C21 C18 C19 C20 176.3(6) . . . . ? C18 C19 C20 N4 3.4(10) . . . . ? C18 C19 C20 C22 -177.2(6) . . . . ? C28 C23 C24 F11 178.6(6) . . . . ? N3 C23 C24 F11 4.2(9) . . . . ? C28 C23 C24 C25 -1.0(10) . . . . ? N3 C23 C24 C25 -175.4(6) . . . . ? F11 C24 C25 F12 1.3(10) . . . . ? C23 C24 C25 F12 -179.1(6) . . . . ? F11 C24 C25 C26 179.7(6) . . . . ? C23 C24 C25 C26 -0.8(10) . . . . ? F12 C25 C26 F13 -2.0(9) . . . . ? C24 C25 C26 F13 179.7(6) . . . . ? F12 C25 C26 C27 179.8(6) . . . . ? C24 C25 C26 C27 1.5(10) . . . . ? F13 C26 C27 F14 0.6(9) . . . . ? C25 C26 C27 F14 178.9(6) . . . . ? F13 C26 C27 C28 -178.6(5) . . . . ? C25 C26 C27 C28 -0.4(10) . . . . ? C24 C23 C28 F15 -178.9(5) . . . . ? N3 C23 C28 F15 -4.6(9) . . . . ? C24 C23 C28 C27 2.1(9) . . . . ? N3 C23 C28 C27 176.4(5) . . . . ? F14 C27 C28 F15 0.4(9) . . . . ? C26 C27 C28 F15 179.6(6) . . . . ? F14 C27 C28 C23 179.3(6) . . . . ? C26 C27 C28 C23 -1.4(10) . . . . ? C34 C29 C30 F16 -175.2(5) . . . . ? N4 C29 C30 F16 0.7(9) . . . . ? C34 C29 C30 C31 0.1(10) . . . . ? N4 C29 C30 C31 176.0(6) . . . . ? F16 C30 C31 F17 -3.6(10) . . . . ? C29 C30 C31 F17 -178.9(6) . . . . ? F16 C30 C31 C32 176.7(6) . . . . ? C29 C30 C31 C32 1.4(10) . . . . ? F17 C31 C32 F18 1.6(10) . . . . ? C30 C31 C32 F18 -178.7(6) . . . . ? F17 C31 C32 C33 178.6(7) . . . . ? C30 C31 C32 C33 -1.7(11) . . . . ? F18 C32 C33 F19 -1.3(11) . . . . ? C31 C32 C33 F19 -178.2(6) . . . . ? F18 C32 C33 C34 177.5(6) . . . . ? C31 C32 C33 C34 0.5(11) . . . . ? C30 C29 C34 F20 178.8(6) . . . . ? N4 C29 C34 F20 2.9(9) . . . . ? C30 C29 C34 C33 -1.3(9) . . . . ? N4 C29 C34 C33 -177.2(6) . . . . ? F19 C33 C34 F20 -0.3(10) . . . . ? C32 C33 C34 F20 -179.0(6) . . . . ? F19 C33 C34 C29 179.8(6) . . . . ? C32 C33 C34 C29 1.0(10) . . . . ? C2 C1 N1 B1 -1.2(9) . . . . ? C4 C1 N1 B1 179.6(6) . . . . ? C2 C1 N1 C6 -179.5(6) . . . . ? C4 C1 N1 C6 1.3(9) . . . . ? N2 B1 N1 C1 -2.3(9) . . . . ? Cl1 B1 N1 C1 178.3(5) . . . . ? N2 B1 N1 C6 175.9(6) . . . . ? Cl1 B1 N1 C6 -3.4(9) . . . . ? C11 C6 N1 C1 103.4(7) . . . . ? C7 C6 N1 C1 -79.6(7) . . . . ? C11 C6 N1 B1 -74.9(8) . . . . ? C7 C6 N1 B1 102.1(7) . . . . ? C2 C3 N2 B1 -2.6(9) . . . . ? C5 C3 N2 B1 176.7(6) . . . . ? C2 C3 N2 C12 176.8(6) . . . . ? C5 C3 N2 C12 -3.9(8) . . . . ? N1 B1 N2 C3 4.3(9) . . . . ? Cl1 B1 N2 C3 -176.3(5) . . . . ? N1 B1 N2 C12 -175.1(5) . . . . ? Cl1 B1 N2 C12 4.3(9) . . . . ? C17 C12 N2 C3 -89.9(7) . . . . ? C13 C12 N2 C3 95.0(7) . . . . ? C17 C12 N2 B1 89.5(8) . . . . ? C13 C12 N2 B1 -85.6(8) . . . . ? C19 C18 N3 B2 0.5(9) . . . . ? C21 C18 N3 B2 -179.4(6) . . . . ? C19 C18 N3 C23 178.2(6) . . . . ? C21 C18 N3 C23 -1.8(9) . . . . ? N4 B2 N3 C18 2.5(9) . . . . ? Cl2 B2 N3 C18 -177.8(5) . . . . ? N4 B2 N3 C23 -175.2(5) . . . . ? Cl2 B2 N3 C23 4.5(9) . . . . ? C28 C23 N3 C18 101.7(7) . . . . ? C24 C23 N3 C18 -84.1(7) . . . . ? C28 C23 N3 B2 -80.6(8) . . . . ? C24 C23 N3 B2 93.6(7) . . . . ? C19 C20 N4 B2 -0.1(9) . . . . ? C22 C20 N4 B2 -179.5(6) . . . . ? C19 C20 N4 C29 -175.4(6) . . . . ? C22 C20 N4 C29 5.2(9) . . . . ? N3 B2 N4 C20 -2.7(9) . . . . ? Cl2 B2 N4 C20 177.6(5) . . . . ? N3 B2 N4 C29 172.7(6) . . . . ? Cl2 B2 N4 C29 -6.9(9) . . . . ? C30 C29 N4 C20 105.0(7) . . . . ? C34 C29 N4 C20 -79.2(8) . . . . ? C30 C29 N4 B2 -70.5(8) . . . . ? C34 C29 N4 B2 105.3(7) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.606 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.107