# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound16 _database_code_depnum_ccdc_archive 'CCDC 847434' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ' C22 H38 B12 N4, C H2 Cl2 ' _chemical_formula_sum 'C23 H40 B12 Cl2 N4' _chemical_formula_weight 573.21 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 34.6741(8) _cell_length_b 9.9071(2) _cell_length_c 19.1591(3) _cell_angle_alpha 90.00 _cell_angle_beta 111.5852(12) _cell_angle_gamma 90.00 _cell_volume 6120.0(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 24205 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description fragme _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2400 _exptl_absorpt_coefficient_mu 0.236 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9544 _exptl_absorpt_correction_T_max 0.9814 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 40700 _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -44 _diffrn_reflns_limit_h_max 44 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.49 _reflns_number_total 7007 _reflns_number_gt 5643 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0521P)^2^+4.2494P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7007 _refine_ls_number_parameters 530 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0544 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1078 _refine_ls_wR_factor_gt 0.1000 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 N1 N 0.07533(3) 0.02570(11) 0.06286(6) 0.0163(2) Uani 1 1 d . . . N2 N 0.07691(3) 0.17247(12) 0.15718(6) 0.0175(2) Uani 1 1 d . . . N3 N 0.19376(3) 0.26512(12) 0.18833(6) 0.0186(2) Uani 1 1 d . . . N4 N 0.16537(3) 0.45487(12) 0.22018(6) 0.0186(2) Uani 1 1 d . . . B1 B 0.08081(4) 0.16494(16) 0.08512(8) 0.0165(3) Uani 1 1 d . . . B2 B 0.16311(5) 0.36801(16) 0.15855(9) 0.0179(3) Uani 1 1 d . . . B3 B 0.08286(5) 0.45117(16) 0.05710(9) 0.0183(3) Uani 1 1 d . . . H3 H 0.0728(5) 0.4726(16) 0.1039(9) 0.020(4) Uiso 1 1 d . . . B4 B 0.04850(5) 0.37865(16) -0.02664(9) 0.0196(3) Uani 1 1 d . . . H4 H 0.0175(5) 0.3538(17) -0.0290(9) 0.027(4) Uiso 1 1 d . . . B5 B 0.07729(5) 0.26511(17) -0.05897(8) 0.0199(3) Uani 1 1 d . . . H5 H 0.0645(5) 0.1720(17) -0.0833(8) 0.022(4) Uiso 1 1 d . . . B6 B 0.12930(5) 0.26611(16) 0.00588(8) 0.0190(3) Uani 1 1 d . . . H6 H 0.1453(5) 0.1739(16) 0.0196(8) 0.016(4) Uiso 1 1 d . . . B7 B 0.12106(5) 0.54552(16) 0.03639(9) 0.0207(3) Uani 1 1 d . . . H7 H 0.1360(5) 0.6282(17) 0.0720(9) 0.024(4) Uiso 1 1 d . . . B8 B 0.06878(5) 0.54281(17) -0.02760(9) 0.0218(3) Uani 1 1 d . . . H8 H 0.0503(5) 0.6281(17) -0.0355(9) 0.022(4) Uiso 1 1 d . . . B9 B 0.06541(5) 0.42649(17) -0.10046(9) 0.0227(3) Uani 1 1 d . . . H9 H 0.0426(5) 0.4377(17) -0.1589(9) 0.024(4) Uiso 1 1 d . . . B10 B 0.11579(5) 0.35547(17) -0.07982(9) 0.0227(3) Uani 1 1 d . . . H10 H 0.1265(5) 0.3184(17) -0.1226(9) 0.025(4) Uiso 1 1 d . . . B11 B 0.15015(5) 0.42980(17) 0.00451(9) 0.0211(3) Uani 1 1 d . . . H11 H 0.1826(5) 0.4396(17) 0.0207(9) 0.024(4) Uiso 1 1 d . . . B12 B 0.11030(5) 0.52969(17) -0.06142(9) 0.0233(3) Uani 1 1 d . . . H12 H 0.1179(5) 0.6084(18) -0.0920(10) 0.030(5) Uiso 1 1 d . . . C1 C 0.06714(4) -0.04685(14) 0.11866(7) 0.0174(3) Uani 1 1 d . . . C2 C 0.05823(4) -0.18289(15) 0.12202(8) 0.0198(3) Uani 1 1 d . . . H2 H 0.0573(5) -0.2432(17) 0.0820(9) 0.024(4) Uiso 1 1 d . . . C3 C 0.04990(5) -0.22769(16) 0.18400(8) 0.0233(3) Uani 1 1 d . . . H3A H 0.0426(5) -0.3206(18) 0.1862(9) 0.023(4) Uiso 1 1 d . . . C4 C 0.05111(5) -0.13901(16) 0.24113(8) 0.0244(3) Uani 1 1 d . . . H4A H 0.0440(5) -0.1730(17) 0.2840(9) 0.024(4) Uiso 1 1 d . . . C5 C 0.06035(4) -0.00293(16) 0.23821(8) 0.0225(3) Uani 1 1 d . . . H5A H 0.0612(5) 0.0579(18) 0.2774(10) 0.029(4) Uiso 1 1 d . . . C6 C 0.06824(4) 0.04257(14) 0.17593(7) 0.0182(3) Uani 1 1 d . . . C7 C 0.07774(4) -0.04942(14) -0.00133(7) 0.0180(3) Uani 1 1 d . . . H7A H 0.0951(5) -0.0007(16) -0.0218(8) 0.015(4) Uiso 1 1 d . . . H7B H 0.0918(5) -0.1367(16) 0.0168(8) 0.016(4) Uiso 1 1 d . . . C8 C 0.03537(5) -0.07699(16) -0.06132(8) 0.0228(3) Uani 1 1 d . . . H8A H 0.0211(5) 0.0068(19) -0.0819(9) 0.029(4) Uiso 1 1 d . . . H8B H 0.0390(5) -0.1342(18) -0.1015(10) 0.027(4) Uiso 1 1 d . . . H8C H 0.0169(5) -0.1305(18) -0.0426(10) 0.031(5) Uiso 1 1 d . . . C9 C 0.07898(5) 0.28320(15) 0.20933(8) 0.0213(3) Uani 1 1 d . . . H9A H 0.0940(5) 0.2483(17) 0.2613(9) 0.024(4) Uiso 1 1 d . . . H9B H 0.0964(5) 0.3544(16) 0.2007(8) 0.017(4) Uiso 1 1 d . . . C10 C 0.03645(5) 0.33777(18) 0.20007(10) 0.0298(4) Uani 1 1 d . . . H10A H 0.0179(6) 0.266(2) 0.2059(10) 0.038(5) Uiso 1 1 d . . . H10B H 0.0385(6) 0.408(2) 0.2372(11) 0.044(5) Uiso 1 1 d . . . H10C H 0.0220(6) 0.3781(19) 0.1507(11) 0.037(5) Uiso 1 1 d . . . C11 C 0.21193(4) 0.28437(14) 0.26618(8) 0.0197(3) Uani 1 1 d . . . C12 C 0.24159(4) 0.20765(16) 0.32063(8) 0.0235(3) Uani 1 1 d . . . H12A H 0.2524(5) 0.1254(17) 0.3081(9) 0.021(4) Uiso 1 1 d . . . C13 C 0.25396(5) 0.25027(17) 0.39493(8) 0.0265(3) Uani 1 1 d . . . H13A H 0.2756(5) 0.1965(18) 0.4333(9) 0.028(4) Uiso 1 1 d . . . C14 C 0.23692(5) 0.36477(17) 0.41405(8) 0.0265(3) Uani 1 1 d . . . H14A H 0.2461(5) 0.3923(18) 0.4659(10) 0.030(5) Uiso 1 1 d . . . C15 C 0.20717(5) 0.44162(16) 0.35992(8) 0.0234(3) Uani 1 1 d . . . H15A H 0.1956(5) 0.5190(18) 0.3739(9) 0.023(4) Uiso 1 1 d . . . C16 C 0.19484(4) 0.40004(14) 0.28549(8) 0.0194(3) Uani 1 1 d . . . C17 C 0.20886(4) 0.15361(15) 0.15495(8) 0.0215(3) Uani 1 1 d . . . H17A H 0.2048(5) 0.1776(17) 0.1027(9) 0.021(4) Uiso 1 1 d . . . H17B H 0.2396(5) 0.1467(16) 0.1834(9) 0.019(4) Uiso 1 1 d . . . C18 C 0.18867(5) 0.01950(16) 0.15961(10) 0.0264(3) Uani 1 1 d . . . H18A H 0.1586(6) 0.0235(19) 0.1352(10) 0.035(5) Uiso 1 1 d . . . H18B H 0.1996(6) -0.050(2) 0.1385(10) 0.038(5) Uiso 1 1 d . . . H18C H 0.1932(5) -0.0002(19) 0.2117(11) 0.035(5) Uiso 1 1 d . . . C19 C 0.14234(4) 0.57590(15) 0.22649(8) 0.0209(3) Uani 1 1 d . . . H19A H 0.1180(5) 0.5833(16) 0.1820(9) 0.018(4) Uiso 1 1 d . . . H19B H 0.1318(5) 0.5586(17) 0.2678(9) 0.022(4) Uiso 1 1 d . . . C20 C 0.16704(5) 0.70605(16) 0.23820(9) 0.0263(3) Uani 1 1 d . . . H20A H 0.1775(5) 0.7196(19) 0.1960(10) 0.035(5) Uiso 1 1 d . . . H20B H 0.1486(6) 0.782(2) 0.2371(10) 0.035(5) Uiso 1 1 d . . . H20C H 0.1909(6) 0.7035(18) 0.2872(10) 0.032(5) Uiso 1 1 d . . . C21 C 0.08850(4) 0.28531(14) 0.03592(7) 0.0167(3) Uani 1 1 d . . . C22 C 0.13180(4) 0.38608(13) 0.07348(7) 0.0172(3) Uani 1 1 d . . . Cl1 Cl 0.213847(15) -0.12077(5) 0.42882(3) 0.04936(14) Uani 1 1 d . . . Cl2 Cl 0.157869(14) 0.10480(5) 0.42017(3) 0.04001(12) Uani 1 1 d . . . C23 C 0.17129(6) -0.0249(2) 0.37074(11) 0.0375(4) Uani 1 1 d . . . H23A H 0.1474(7) -0.081(2) 0.3530(12) 0.052(6) Uiso 1 1 d . . . H23B H 0.1793(6) 0.018(2) 0.3325(11) 0.046(6) Uiso 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 N1 0.0177(5) 0.0166(6) 0.0154(5) 0.0005(4) 0.0070(4) -0.0006(4) N2 0.0197(6) 0.0173(6) 0.0160(5) -0.0013(4) 0.0072(4) -0.0020(5) N3 0.0188(6) 0.0173(6) 0.0198(6) -0.0014(5) 0.0070(4) -0.0009(5) N4 0.0181(6) 0.0178(6) 0.0190(6) -0.0017(5) 0.0058(4) -0.0006(4) B1 0.0144(7) 0.0179(7) 0.0164(7) 0.0003(6) 0.0046(5) -0.0003(6) B2 0.0177(7) 0.0165(7) 0.0212(7) -0.0018(6) 0.0091(6) -0.0028(6) B3 0.0192(7) 0.0155(7) 0.0196(7) -0.0005(6) 0.0063(6) 0.0003(6) B4 0.0216(8) 0.0178(8) 0.0174(7) -0.0004(6) 0.0050(6) -0.0006(6) B5 0.0261(8) 0.0184(8) 0.0152(7) -0.0004(6) 0.0076(6) -0.0013(6) B6 0.0235(8) 0.0173(8) 0.0187(7) -0.0020(6) 0.0109(6) -0.0009(6) B7 0.0250(8) 0.0148(7) 0.0221(8) 0.0000(6) 0.0086(6) 0.0000(6) B8 0.0256(8) 0.0172(8) 0.0199(7) 0.0010(6) 0.0053(6) 0.0003(6) B9 0.0304(9) 0.0178(8) 0.0188(7) 0.0020(6) 0.0078(6) -0.0010(7) B10 0.0321(9) 0.0196(8) 0.0194(8) 0.0016(6) 0.0130(7) -0.0014(7) B11 0.0245(8) 0.0186(8) 0.0231(8) 0.0000(6) 0.0122(6) -0.0023(6) B12 0.0315(9) 0.0173(8) 0.0217(8) 0.0021(6) 0.0105(7) -0.0026(7) C1 0.0151(6) 0.0199(7) 0.0166(6) 0.0025(5) 0.0051(5) 0.0011(5) C2 0.0185(7) 0.0187(7) 0.0224(7) 0.0022(6) 0.0077(5) 0.0007(5) C3 0.0220(7) 0.0210(8) 0.0259(7) 0.0067(6) 0.0077(6) -0.0012(6) C4 0.0233(7) 0.0301(8) 0.0202(7) 0.0075(6) 0.0087(6) -0.0014(6) C5 0.0230(7) 0.0271(8) 0.0173(7) 0.0004(6) 0.0073(5) -0.0022(6) C6 0.0162(6) 0.0201(7) 0.0173(6) 0.0013(5) 0.0049(5) -0.0007(5) C7 0.0217(7) 0.0154(7) 0.0185(6) -0.0011(5) 0.0092(5) 0.0001(5) C8 0.0250(8) 0.0201(7) 0.0208(7) -0.0020(6) 0.0056(6) -0.0032(6) C9 0.0260(7) 0.0219(7) 0.0166(7) -0.0058(6) 0.0087(6) -0.0047(6) C10 0.0313(8) 0.0305(9) 0.0336(9) -0.0118(7) 0.0191(7) -0.0042(7) C11 0.0193(7) 0.0200(7) 0.0202(7) 0.0000(5) 0.0078(5) -0.0044(5) C12 0.0197(7) 0.0226(8) 0.0273(7) 0.0038(6) 0.0076(6) -0.0016(6) C13 0.0233(7) 0.0290(8) 0.0242(7) 0.0073(6) 0.0054(6) -0.0044(6) C14 0.0268(8) 0.0339(9) 0.0180(7) 0.0010(6) 0.0073(6) -0.0087(6) C15 0.0238(7) 0.0262(8) 0.0215(7) -0.0027(6) 0.0099(6) -0.0049(6) C16 0.0174(6) 0.0202(7) 0.0204(7) 0.0004(5) 0.0069(5) -0.0032(5) C17 0.0202(7) 0.0199(7) 0.0255(7) -0.0022(6) 0.0096(6) 0.0032(6) C18 0.0256(8) 0.0190(8) 0.0343(9) -0.0033(6) 0.0107(7) 0.0014(6) C19 0.0194(7) 0.0207(7) 0.0221(7) -0.0054(6) 0.0072(6) 0.0008(6) C20 0.0242(8) 0.0209(8) 0.0317(8) -0.0066(6) 0.0078(6) -0.0008(6) C21 0.0184(6) 0.0152(6) 0.0161(6) -0.0026(5) 0.0059(5) -0.0015(5) C22 0.0192(6) 0.0148(6) 0.0194(6) -0.0018(5) 0.0093(5) -0.0021(5) Cl1 0.0372(3) 0.0443(3) 0.0575(3) -0.0174(2) 0.0067(2) 0.0030(2) Cl2 0.0369(2) 0.0366(2) 0.0522(3) -0.01252(19) 0.0231(2) -0.00496(18) C23 0.0383(10) 0.0371(10) 0.0389(10) -0.0076(8) 0.0162(8) -0.0022(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 N1 C1 1.4011(17) . ? N1 B1 1.4358(19) . ? N1 C7 1.4660(17) . ? N2 C6 1.3982(18) . ? N2 B1 1.4379(18) . ? N2 C9 1.4677(18) . ? N3 C11 1.4024(18) . ? N3 B2 1.431(2) . ? N3 C17 1.4663(18) . ? N4 C16 1.4015(18) . ? N4 B2 1.4398(19) . ? N4 C19 1.4700(18) . ? B1 C21 1.602(2) . ? B2 C22 1.602(2) . ? B3 C21 1.721(2) . ? B3 C22 1.733(2) . ? B3 B4 1.762(2) . ? B3 B8 1.764(2) . ? B3 B7 1.781(2) . ? B3 H3 1.095(15) . ? B4 C21 1.730(2) . ? B4 B5 1.761(2) . ? B4 B8 1.775(2) . ? B4 B9 1.783(2) . ? B4 H4 1.086(17) . ? B5 C21 1.7252(19) . ? B5 B9 1.765(2) . ? B5 B10 1.771(2) . ? B5 B6 1.774(2) . ? B5 H5 1.055(17) . ? B6 C21 1.723(2) . ? B6 C22 1.736(2) . ? B6 B10 1.770(2) . ? B6 B11 1.780(2) . ? B6 H6 1.051(16) . ? B7 C22 1.716(2) . ? B7 B8 1.776(2) . ? B7 B11 1.777(2) . ? B7 B12 1.778(2) . ? B7 H7 1.070(17) . ? B8 B9 1.781(2) . ? B8 B12 1.788(2) . ? B8 H8 1.039(17) . ? B9 B12 1.781(2) . ? B9 B10 1.787(2) . ? B9 H9 1.114(16) . ? B10 B11 1.776(2) . ? B10 B12 1.786(2) . ? B10 H10 1.081(16) . ? B11 C22 1.720(2) . ? B11 B12 1.789(2) . ? B11 H11 1.056(16) . ? B12 H12 1.064(18) . ? C1 C2 1.390(2) . ? C1 C6 1.4000(19) . ? C2 C3 1.394(2) . ? C2 H2 0.964(17) . ? C3 C4 1.392(2) . ? C3 H3A 0.960(18) . ? C4 C5 1.392(2) . ? C4 H4A 0.998(16) . ? C5 C6 1.3934(19) . ? C5 H5A 0.954(18) . ? C7 C8 1.520(2) . ? C7 H7A 0.959(15) . ? C7 H7B 0.991(16) . ? C8 H8A 0.973(19) . ? C8 H8B 1.000(18) . ? C8 H8C 0.994(18) . ? C9 C10 1.519(2) . ? C9 H9A 1.001(17) . ? C9 H9B 0.981(16) . ? C10 H10A 0.99(2) . ? C10 H10B 0.98(2) . ? C10 H10C 0.98(2) . ? C11 C12 1.391(2) . ? C11 C16 1.401(2) . ? C12 C13 1.393(2) . ? C12 H12A 0.964(17) . ? C13 C14 1.389(2) . ? C13 H13A 0.990(18) . ? C14 C15 1.390(2) . ? C14 H14A 0.964(18) . ? C15 C16 1.392(2) . ? C15 H15A 0.947(18) . ? C17 C18 1.520(2) . ? C17 H17A 0.988(16) . ? C17 H17B 1.004(16) . ? C18 H18A 0.975(19) . ? C18 H18B 0.95(2) . ? C18 H18C 0.971(19) . ? C19 C20 1.518(2) . ? C19 H19A 0.956(16) . ? C19 H19B 1.002(16) . ? C20 H20A 1.011(19) . ? C20 H20B 0.981(19) . ? C20 H20C 0.998(18) . ? C21 C22 1.7246(19) . ? Cl1 C23 1.763(2) . ? Cl2 C23 1.7575(18) . ? C23 H23A 0.95(2) . ? C23 H23B 0.97(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 C1 N1 B1 107.95(11) . . ? C1 N1 C7 118.02(11) . . ? B1 N1 C7 134.01(11) . . ? C6 N2 B1 107.70(11) . . ? C6 N2 C9 118.32(11) . . ? B1 N2 C9 133.95(12) . . ? C11 N3 B2 107.72(11) . . ? C11 N3 C17 118.26(12) . . ? B2 N3 C17 134.01(12) . . ? C16 N4 B2 107.60(11) . . ? C16 N4 C19 118.84(11) . . ? B2 N4 C19 133.45(12) . . ? N1 B1 N2 106.62(12) . . ? N1 B1 C21 124.95(12) . . ? N2 B1 C21 128.41(12) . . ? N3 B2 N4 106.88(12) . . ? N3 B2 C22 127.68(12) . . ? N4 B2 C22 125.43(13) . . ? C21 B3 C22 59.91(8) . . ? C21 B3 B4 59.55(8) . . ? C22 B3 B4 107.60(11) . . ? C21 B3 B8 106.94(11) . . ? C22 B3 B8 106.21(11) . . ? B4 B3 B8 60.44(9) . . ? C21 B3 B7 106.87(11) . . ? C22 B3 B7 58.44(8) . . ? B4 B3 B7 108.69(11) . . ? B8 B3 B7 60.12(9) . . ? C21 B3 H3 118.4(8) . . ? C22 B3 H3 120.6(8) . . ? B4 B3 H3 120.8(8) . . ? B8 B3 H3 126.1(8) . . ? B7 B3 H3 124.5(8) . . ? C21 B4 B5 59.23(8) . . ? C21 B4 B3 59.05(8) . . ? B5 B4 B3 107.45(11) . . ? C21 B4 B8 106.09(11) . . ? B5 B4 B8 107.66(11) . . ? B3 B4 B8 59.86(9) . . ? C21 B4 B9 106.12(11) . . ? B5 B4 B9 59.75(9) . . ? B3 B4 B9 107.72(11) . . ? B8 B4 B9 60.06(9) . . ? C21 B4 H4 115.9(9) . . ? B5 B4 H4 121.3(9) . . ? B3 B4 H4 117.3(9) . . ? B8 B4 H4 126.7(9) . . ? B9 B4 H4 129.5(9) . . ? C21 B5 B4 59.49(8) . . ? C21 B5 B9 107.11(11) . . ? B4 B5 B9 60.75(9) . . ? C21 B5 B10 106.43(11) . . ? B4 B5 B10 109.18(11) . . ? B9 B5 B10 60.72(10) . . ? C21 B5 B6 58.96(8) . . ? B4 B5 B6 108.17(11) . . ? B9 B5 B6 108.60(12) . . ? B10 B5 B6 59.92(9) . . ? C21 B5 H5 117.5(8) . . ? B4 B5 H5 120.8(9) . . ? B9 B5 H5 127.1(9) . . ? B10 B5 H5 125.0(8) . . ? B6 B5 H5 118.0(9) . . ? C21 B6 C22 59.81(8) . . ? C21 B6 B10 106.57(11) . . ? C22 B6 B10 105.85(11) . . ? C21 B6 B5 59.11(8) . . ? C22 B6 B5 106.58(11) . . ? B10 B6 B5 59.95(9) . . ? C21 B6 B11 107.00(11) . . ? C22 B6 B11 58.55(8) . . ? B10 B6 B11 60.05(9) . . ? B5 B6 B11 107.97(11) . . ? C21 B6 H6 115.8(8) . . ? C22 B6 H6 122.2(8) . . ? B10 B6 H6 127.0(8) . . ? B5 B6 H6 118.5(8) . . ? B11 B6 H6 128.0(8) . . ? C22 B7 B8 106.44(11) . . ? C22 B7 B11 58.95(8) . . ? B8 B7 B11 108.49(11) . . ? C22 B7 B12 106.54(11) . . ? B8 B7 B12 60.39(9) . . ? B11 B7 B12 60.42(9) . . ? C22 B7 B3 59.37(9) . . ? B8 B7 B3 59.47(9) . . ? B11 B7 B3 107.50(11) . . ? B12 B7 B3 107.67(11) . . ? C22 B7 H7 117.4(9) . . ? B8 B7 H7 125.7(9) . . ? B11 B7 H7 120.7(9) . . ? B12 B7 H7 127.2(9) . . ? B3 B7 H7 119.0(9) . . ? B3 B8 B4 59.70(9) . . ? B3 B8 B7 60.40(9) . . ? B4 B8 B7 108.33(11) . . ? B3 B8 B9 107.71(11) . . ? B4 B8 B9 60.20(9) . . ? B7 B8 B9 107.88(12) . . ? B3 B8 B12 107.99(11) . . ? B4 B8 B12 108.20(12) . . ? B7 B8 B12 59.86(9) . . ? B9 B8 B12 59.87(9) . . ? B3 B8 H8 120.0(9) . . ? B4 B8 H8 121.4(9) . . ? B7 B8 H8 120.5(9) . . ? B9 B8 H8 123.6(9) . . ? B12 B8 H8 122.9(9) . . ? B5 B9 B8 107.22(11) . . ? B5 B9 B12 107.92(12) . . ? B8 B9 B12 60.26(9) . . ? B5 B9 B4 59.50(9) . . ? B8 B9 B4 59.74(9) . . ? B12 B9 B4 108.13(11) . . ? B5 B9 B10 59.78(9) . . ? B8 B9 B10 107.72(11) . . ? B12 B9 B10 60.06(10) . . ? B4 B9 B10 107.44(11) . . ? B5 B9 H9 120.3(9) . . ? B8 B9 H9 122.8(9) . . ? B12 B9 H9 123.6(9) . . ? B4 B9 H9 120.3(8) . . ? B10 B9 H9 122.4(8) . . ? B6 B10 B5 60.13(9) . . ? B6 B10 B11 60.24(9) . . ? B5 B10 B11 108.27(11) . . ? B6 B10 B12 108.14(11) . . ? B5 B10 B12 107.47(12) . . ? B11 B10 B12 60.29(9) . . ? B6 B10 B9 107.79(11) . . ? B5 B10 B9 59.49(9) . . ? B11 B10 B9 108.18(11) . . ? B12 B10 B9 59.78(9) . . ? B6 B10 H10 119.1(9) . . ? B5 B10 H10 119.8(9) . . ? B11 B10 H10 121.8(9) . . ? B12 B10 H10 124.7(9) . . ? B9 B10 H10 123.1(9) . . ? C22 B11 B10 106.29(11) . . ? C22 B11 B7 58.74(8) . . ? B10 B11 B7 107.73(12) . . ? C22 B11 B6 59.46(8) . . ? B10 B11 B6 59.71(9) . . ? B7 B11 B6 107.31(11) . . ? C22 B11 B12 105.90(11) . . ? B10 B11 B12 60.11(9) . . ? B7 B11 B12 59.81(9) . . ? B6 B11 B12 107.58(11) . . ? C22 B11 H11 116.9(9) . . ? B10 B11 H11 126.3(9) . . ? B7 B11 H11 121.2(9) . . ? B6 B11 H11 118.3(9) . . ? B12 B11 H11 128.3(9) . . ? B7 B12 B9 107.78(12) . . ? B7 B12 B10 107.28(11) . . ? B9 B12 B10 60.15(10) . . ? B7 B12 B8 59.75(9) . . ? B9 B12 B8 59.87(9) . . ? B10 B12 B8 107.48(11) . . ? B7 B12 B11 59.77(9) . . ? B9 B12 B11 107.92(11) . . ? B10 B12 B11 59.60(9) . . ? B8 B12 B11 107.47(11) . . ? B7 B12 H12 121.1(9) . . ? B9 B12 H12 122.9(9) . . ? B10 B12 H12 122.3(9) . . ? B8 B12 H12 122.7(9) . . ? B11 B12 H12 120.7(9) . . ? C2 C1 C6 121.32(12) . . ? C2 C1 N1 130.08(12) . . ? C6 C1 N1 108.59(12) . . ? C1 C2 C3 117.88(14) . . ? C1 C2 H2 120.4(10) . . ? C3 C2 H2 121.7(10) . . ? C4 C3 C2 120.87(14) . . ? C4 C3 H3A 120.3(10) . . ? C2 C3 H3A 118.8(10) . . ? C5 C4 C3 121.37(13) . . ? C5 C4 H4A 119.3(10) . . ? C3 C4 H4A 119.3(10) . . ? C4 C5 C6 117.94(14) . . ? C4 C5 H5A 121.4(11) . . ? C6 C5 H5A 120.7(11) . . ? C5 C6 N2 130.26(13) . . ? C5 C6 C1 120.61(13) . . ? N2 C6 C1 109.11(11) . . ? N1 C7 C8 112.82(11) . . ? N1 C7 H7A 109.0(9) . . ? C8 C7 H7A 111.0(9) . . ? N1 C7 H7B 108.7(8) . . ? C8 C7 H7B 108.8(9) . . ? H7A C7 H7B 106.4(13) . . ? C7 C8 H8A 111.0(10) . . ? C7 C8 H8B 108.8(10) . . ? H8A C8 H8B 111.2(14) . . ? C7 C8 H8C 113.2(10) . . ? H8A C8 H8C 107.7(14) . . ? H8B C8 H8C 104.9(14) . . ? N2 C9 C10 112.60(12) . . ? N2 C9 H9A 107.3(10) . . ? C10 C9 H9A 111.6(9) . . ? N2 C9 H9B 107.6(9) . . ? C10 C9 H9B 110.8(9) . . ? H9A C9 H9B 106.8(13) . . ? C9 C10 H10A 111.8(11) . . ? C9 C10 H10B 111.1(12) . . ? H10A C10 H10B 107.9(15) . . ? C9 C10 H10C 112.8(11) . . ? H10A C10 H10C 106.3(15) . . ? H10B C10 H10C 106.6(16) . . ? C12 C11 C16 121.13(13) . . ? C12 C11 N3 129.97(13) . . ? C16 C11 N3 108.90(12) . . ? C11 C12 C13 117.76(14) . . ? C11 C12 H12A 121.6(10) . . ? C13 C12 H12A 120.6(10) . . ? C14 C13 C12 121.09(14) . . ? C14 C13 H13A 121.5(10) . . ? C12 C13 H13A 117.4(10) . . ? C13 C14 C15 121.42(14) . . ? C13 C14 H14A 119.4(11) . . ? C15 C14 H14A 119.2(11) . . ? C14 C15 C16 117.79(15) . . ? C14 C15 H15A 120.5(10) . . ? C16 C15 H15A 121.7(10) . . ? C15 C16 C11 120.81(13) . . ? C15 C16 N4 130.41(14) . . ? C11 C16 N4 108.76(12) . . ? N3 C17 C18 112.77(12) . . ? N3 C17 H17A 108.7(10) . . ? C18 C17 H17A 111.9(10) . . ? N3 C17 H17B 107.0(9) . . ? C18 C17 H17B 109.1(9) . . ? H17A C17 H17B 107.2(12) . . ? C17 C18 H18A 111.8(11) . . ? C17 C18 H18B 110.1(12) . . ? H18A C18 H18B 110.6(16) . . ? C17 C18 H18C 109.4(11) . . ? H18A C18 H18C 104.0(15) . . ? H18B C18 H18C 110.8(16) . . ? N4 C19 C20 114.26(12) . . ? N4 C19 H19A 108.5(9) . . ? C20 C19 H19A 109.3(10) . . ? N4 C19 H19B 107.0(10) . . ? C20 C19 H19B 112.3(9) . . ? H19A C19 H19B 105.1(13) . . ? C19 C20 H20A 110.1(11) . . ? C19 C20 H20B 108.5(11) . . ? H20A C20 H20B 107.8(15) . . ? C19 C20 H20C 110.2(11) . . ? H20A C20 H20C 109.8(14) . . ? H20B C20 H20C 110.4(15) . . ? B1 C21 B3 120.93(11) . . ? B1 C21 B6 116.69(11) . . ? B3 C21 B6 111.27(10) . . ? B1 C21 C22 119.55(10) . . ? B3 C21 C22 60.39(8) . . ? B6 C21 C22 60.49(8) . . ? B1 C21 B5 120.80(11) . . ? B3 C21 B5 110.99(10) . . ? B6 C21 B5 61.93(9) . . ? C22 C21 B5 109.32(10) . . ? B1 C21 B4 122.75(11) . . ? B3 C21 B4 61.40(9) . . ? B6 C21 B4 112.04(10) . . ? C22 C21 B4 109.44(10) . . ? B5 C21 B4 61.29(9) . . ? B2 C22 B7 119.14(11) . . ? B2 C22 B11 120.42(11) . . ? B7 C22 B11 62.31(9) . . ? B2 C22 C21 121.34(11) . . ? B7 C22 C21 109.70(10) . . ? B11 C22 C21 109.67(10) . . ? B2 C22 B3 118.55(11) . . ? B7 C22 B3 62.19(9) . . ? B11 C22 B3 112.44(11) . . ? C21 C22 B3 59.70(8) . . ? B2 C22 B6 120.78(11) . . ? B7 C22 B6 112.19(10) . . ? B11 C22 B6 61.99(9) . . ? C21 C22 B6 59.70(8) . . ? B3 C22 B6 110.04(10) . . ? Cl2 C23 Cl1 112.32(10) . . ? Cl2 C23 H23A 104.6(13) . . ? Cl1 C23 H23A 109.0(13) . . ? Cl2 C23 H23B 106.9(12) . . ? Cl1 C23 H23B 107.8(12) . . ? H23A C23 H23B 116.3(18) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.525 _refine_diff_density_min -0.795 _refine_diff_density_rms 0.053 _vrf_PLAT773_compound1 ; PROBLEM: Suspect C-C Bond in CIF: C21 -- C22 .. 1.72 Ang. RESPONSE: typically for 1,2-dicarbadodecaboran-compounds with bulky ligands ; ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound17 _database_code_depnum_ccdc_archive 'CCDC 847435' _vrf_CHEMW03_compound17 ; PROBLEM: ALERT: The ratio of given/expected molecular weight as RESPONSE: one CH2Cl2 was highly disordered and therefore squeezed by the Platon routine but left in the sum formula for further calculations ; _vrf_PLAT051_compound17 ; PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by . 68.88 % RESPONSE: one CH2Cl2 was highly disordered and therefore squeezed by the Platon routine but left in the sum formula for further calculations ; # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material # Spek, A.L. (2009). Acta Cryst. D65, 148-155. loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.098 0.719 0.108 121 27 ' ' 2 -0.098 0.219 0.392 121 27 ' ' 3 0.098 0.781 0.608 121 27 ' ' 4 -0.098 0.280 0.892 121 27 ' ' _platon_squeeze_details ; one CH2Cl2 was highly disordered and therefore squeezed by the Platon routine but left in the sum formula for further calculations ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H38 B12 N4, 1.0(C H2 Cl2)' _chemical_formula_sum 'C39 H40 B12 Cl2 N4' _chemical_formula_weight 765.37 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 11.24370(10) _cell_length_b 21.5876(3) _cell_length_c 16.9579(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.7367(6) _cell_angle_gamma 90.00 _cell_volume 4014.81(8) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 114240 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 25.028 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1584 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9728 _exptl_absorpt_correction_T_max 0.9902 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13459 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7055 _reflns_number_gt 4636 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; one CH2Cl2 was highly disordered and therefore squeezed by the Platon routine but left in the sum formula for further calculations 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^)+(0.1515P)^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 7055 _refine_ls_number_parameters 527 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1053 _refine_ls_R_factor_gt 0.0759 _refine_ls_wR_factor_ref 0.2362 _refine_ls_wR_factor_gt 0.2171 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 N1 N 0.5751(2) -0.10596(10) 0.88633(13) 0.0396(6) Uani 1 1 d . . . N2 N 0.37453(19) -0.07782(10) 0.83993(13) 0.0382(6) Uani 1 1 d . . . N3 N 0.44022(19) -0.03555(10) 0.63436(13) 0.0382(5) Uani 1 1 d . . . N4 N 0.30698(19) 0.04634(10) 0.62976(12) 0.0360(5) Uani 1 1 d . . . B1 B 0.4976(3) -0.05472(15) 0.85540(18) 0.0373(7) Uani 1 1 d . . . B2 B 0.4187(3) 0.02022(15) 0.67649(18) 0.0360(7) Uani 1 1 d . . . B3 B 0.4398(3) 0.07413(15) 0.83235(19) 0.0382(7) Uani 1 1 d . . . H3 H 0.345(2) 0.0628(12) 0.8296(14) 0.028(6) Uiso 1 1 d . . . B4 B 0.5565(3) 0.06712(15) 0.92171(19) 0.0399(7) Uani 1 1 d . . . H4 H 0.531(3) 0.0471(14) 0.9745(19) 0.054(8) Uiso 1 1 d . . . B5 B 0.6876(3) 0.03776(16) 0.8929(2) 0.0406(8) Uani 1 1 d . . . H5 H 0.739(3) 0.0067(16) 0.922(2) 0.067(10) Uiso 1 1 d . . . B6 B 0.6505(3) 0.02591(16) 0.78649(19) 0.0397(7) Uani 1 1 d . . . H6 H 0.686(2) -0.0133(14) 0.7588(16) 0.046(8) Uiso 1 1 d . . . B7 B 0.6171(3) 0.09935(15) 0.7400(2) 0.0407(7) Uani 1 1 d . . . H7 H 0.626(2) 0.1075(13) 0.6745(16) 0.042(7) Uiso 1 1 d . . . B8 B 0.4872(3) 0.12966(15) 0.76917(19) 0.0381(7) Uani 1 1 d . . . H8 H 0.419(2) 0.1556(13) 0.7299(17) 0.045(7) Uiso 1 1 d . . . B9 B 0.5224(3) 0.14056(15) 0.8757(2) 0.0425(8) Uani 1 1 d . . . H9 H 0.476(3) 0.1791(17) 0.905(2) 0.074(10) Uiso 1 1 d . . . B10 B 0.6770(3) 0.11824(16) 0.9119(2) 0.0433(8) Uani 1 1 d . . . H10 H 0.739(2) 0.1404(13) 0.9693(17) 0.044(7) Uiso 1 1 d . . . B11 B 0.7347(3) 0.09197(16) 0.8284(2) 0.0442(8) Uani 1 1 d . . . H11 H 0.823(4) 0.0977(19) 0.816(2) 0.091(12) Uiso 1 1 d . . . B12 B 0.6333(3) 0.15644(16) 0.8176(2) 0.0434(8) Uani 1 1 d . . . H12 H 0.661(2) 0.2069(12) 0.8072(15) 0.033(6) Uiso 1 1 d . . . C1 C 0.5012(3) -0.15786(13) 0.88936(17) 0.0415(7) Uani 1 1 d . . . C2 C 0.3793(3) -0.14121(13) 0.86114(16) 0.0415(7) Uani 1 1 d . . . C3 C 0.2866(3) -0.18397(14) 0.85800(19) 0.0511(8) Uani 1 1 d . . . H3A H 0.2036 -0.1724 0.8394 0.061 Uiso 1 1 calc R . . C4 C 0.3180(3) -0.24368(15) 0.8825(2) 0.0629(9) Uani 1 1 d . . . H4A H 0.2559 -0.2738 0.8808 0.076 Uiso 1 1 calc R . . C5 C 0.4399(3) -0.26056(15) 0.9098(2) 0.0625(9) Uani 1 1 d . . . H5A H 0.4591 -0.3022 0.9257 0.075 Uiso 1 1 calc R . . C6 C 0.5330(3) -0.21846(14) 0.91435(19) 0.0525(8) Uani 1 1 d . . . H6A H 0.6157 -0.2301 0.9337 0.063 Uiso 1 1 calc R . . C7 C 0.7038(2) -0.11357(12) 0.91652(17) 0.0410(7) Uani 1 1 d . . . C8 C 0.7820(3) -0.11926(13) 0.86463(19) 0.0464(7) Uani 1 1 d . . . H8A H 0.7509 -0.1178 0.8078 0.056 Uiso 1 1 calc R . . C9 C 0.9052(3) -0.12701(15) 0.8951(2) 0.0598(9) Uani 1 1 d . . . H9A H 0.9589 -0.1303 0.8591 0.072 Uiso 1 1 calc R . . C10 C 0.9507(3) -0.13000(16) 0.9765(3) 0.0651(10) Uani 1 1 d . . . H10A H 1.0358 -0.1349 0.9972 0.078 Uiso 1 1 calc R . . C11 C 0.8726(3) -0.12596(16) 1.0288(2) 0.0649(10) Uani 1 1 d . . . H11A H 0.9039 -0.1286 1.0855 0.078 Uiso 1 1 calc R . . C12 C 0.7490(3) -0.11807(14) 0.99867(18) 0.0505(8) Uani 1 1 d . . . H12A H 0.6951 -0.1157 1.0346 0.061 Uiso 1 1 calc R . . C13 C 0.2533(2) -0.05379(12) 0.81102(17) 0.0392(7) Uani 1 1 d . . . C14 C 0.1907(3) -0.06711(13) 0.73428(17) 0.0429(7) Uani 1 1 d . . . H14A H 0.2318 -0.0866 0.6976 0.051 Uiso 1 1 calc R . . C15 C 0.0678(3) -0.05260(15) 0.7091(2) 0.0512(8) Uani 1 1 d . . . H15A H 0.0248 -0.0624 0.6559 0.061 Uiso 1 1 calc R . . C16 C 0.0085(3) -0.02367(15) 0.7624(2) 0.0531(8) Uani 1 1 d . . . H16A H -0.0755 -0.0135 0.7458 0.064 Uiso 1 1 calc R . . C17 C 0.0715(3) -0.00966(15) 0.8397(2) 0.0511(8) Uani 1 1 d . . . H17A H 0.0305 0.0105 0.8758 0.061 Uiso 1 1 calc R . . C18 C 0.1936(3) -0.02455(14) 0.86547(17) 0.0437(7) Uani 1 1 d . . . H18A H 0.2363 -0.0152 0.9190 0.052 Uiso 1 1 calc R . . C19 C 0.3450(2) -0.04165(13) 0.56551(15) 0.0396(7) Uani 1 1 d . . . C20 C 0.2638(2) 0.00762(13) 0.56323(16) 0.0385(7) Uani 1 1 d . . . C21 C 0.1587(3) 0.01131(14) 0.50305(16) 0.0431(7) Uani 1 1 d . . . H21A H 0.1028 0.0445 0.5017 0.052 Uiso 1 1 calc R . . C22 C 0.1373(3) -0.03502(15) 0.44453(17) 0.0504(8) Uani 1 1 d . . . H22A H 0.0652 -0.0340 0.4030 0.060 Uiso 1 1 calc R . . C23 C 0.2210(3) -0.08293(15) 0.44660(18) 0.0520(8) Uani 1 1 d . . . H23A H 0.2055 -0.1135 0.4053 0.062 Uiso 1 1 calc R . . C24 C 0.3249(3) -0.08730(15) 0.50620(17) 0.0486(8) Uani 1 1 d . . . H24A H 0.3811 -0.1203 0.5070 0.058 Uiso 1 1 calc R . . C25 C 0.5297(2) -0.08417(13) 0.64804(16) 0.0391(6) Uani 1 1 d . . . C26 C 0.6348(3) -0.07860(14) 0.61897(17) 0.0465(7) Uani 1 1 d . . . H26A H 0.6521 -0.0412 0.5942 0.056 Uiso 1 1 calc R . . C27 C 0.7152(3) -0.12853(16) 0.62640(19) 0.0571(9) Uani 1 1 d . . . H27A H 0.7892 -0.1246 0.6086 0.068 Uiso 1 1 calc R . . C28 C 0.6875(3) -0.18345(16) 0.6595(2) 0.0617(9) Uani 1 1 d . . . H28A H 0.7411 -0.2178 0.6627 0.074 Uiso 1 1 calc R . . C29 C 0.5815(3) -0.18880(15) 0.6884(2) 0.0569(8) Uani 1 1 d . . . H29A H 0.5632 -0.2264 0.7122 0.068 Uiso 1 1 calc R . . C30 C 0.5031(3) -0.13899(13) 0.68203(17) 0.0466(7) Uani 1 1 d . . . H30A H 0.4301 -0.1425 0.7013 0.056 Uiso 1 1 calc R . . C31 C 0.2364(2) 0.10040(13) 0.63770(16) 0.0373(6) Uani 1 1 d . . . C32 C 0.1630(2) 0.10194(14) 0.69389(17) 0.0444(7) Uani 1 1 d . . . H32A H 0.1620 0.0677 0.7289 0.053 Uiso 1 1 calc R . . C33 C 0.0919(3) 0.15306(15) 0.6988(2) 0.0558(8) Uani 1 1 d . . . H33A H 0.0410 0.1537 0.7367 0.067 Uiso 1 1 calc R . . C34 C 0.0941(3) 0.20312(16) 0.6493(2) 0.0645(9) Uani 1 1 d . . . H34A H 0.0459 0.2386 0.6538 0.077 Uiso 1 1 calc R . . C35 C 0.1658(3) 0.20210(15) 0.5933(2) 0.0596(9) Uani 1 1 d . . . H35A H 0.1663 0.2366 0.5586 0.071 Uiso 1 1 calc R . . C36 C 0.2381(3) 0.15038(14) 0.58735(17) 0.0456(7) Uani 1 1 d . . . H36A H 0.2880 0.1497 0.5489 0.055 Uiso 1 1 calc R . . C37 C 0.5435(2) 0.01425(12) 0.84397(15) 0.0351(6) Uani 1 1 d . . . C38 C 0.5023(2) 0.05124(12) 0.75374(16) 0.0371(6) 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 N1 0.0463(13) 0.0286(13) 0.0445(12) 0.0009(10) 0.0116(10) -0.0027(10) N2 0.0434(13) 0.0301(13) 0.0415(12) 0.0003(9) 0.0102(10) -0.0032(10) N3 0.0423(12) 0.0336(13) 0.0393(12) -0.0015(10) 0.0102(10) 0.0004(10) N4 0.0437(12) 0.0298(13) 0.0359(11) -0.0002(9) 0.0118(10) 0.0023(10) B1 0.0477(18) 0.0309(17) 0.0358(16) -0.0018(13) 0.0149(14) 0.0010(14) B2 0.0422(17) 0.0298(17) 0.0388(16) 0.0019(13) 0.0149(14) -0.0031(13) B3 0.0458(19) 0.0312(18) 0.0383(16) -0.0009(13) 0.0108(14) 0.0006(14) B4 0.0476(18) 0.0350(18) 0.0369(16) -0.0019(13) 0.0088(14) -0.0022(14) B5 0.0436(18) 0.0330(19) 0.0434(17) 0.0001(14) 0.0056(15) -0.0017(15) B6 0.0391(17) 0.0371(19) 0.0449(17) 0.0006(14) 0.0135(14) 0.0005(14) B7 0.0486(18) 0.0278(17) 0.0484(18) 0.0021(14) 0.0166(15) -0.0048(14) B8 0.0449(18) 0.0289(17) 0.0391(16) 0.0012(13) 0.0066(14) -0.0023(14) B9 0.0537(19) 0.0276(17) 0.0482(18) -0.0030(14) 0.0154(16) -0.0038(15) B10 0.0488(19) 0.0352(19) 0.0453(18) -0.0020(15) 0.0090(15) -0.0070(15) B11 0.0465(19) 0.0352(19) 0.0525(19) 0.0021(15) 0.0145(16) -0.0064(15) B12 0.0483(19) 0.0329(19) 0.0501(19) -0.0008(14) 0.0130(15) -0.0064(15) C1 0.0504(17) 0.0281(16) 0.0491(16) 0.0010(12) 0.0176(13) -0.0017(13) C2 0.0539(17) 0.0292(16) 0.0437(15) -0.0008(12) 0.0156(13) -0.0026(13) C3 0.0566(18) 0.0356(18) 0.0629(19) -0.0012(14) 0.0173(15) -0.0096(14) C4 0.074(2) 0.0333(19) 0.084(2) 0.0035(16) 0.0239(19) -0.0160(16) C5 0.083(3) 0.0283(17) 0.079(2) 0.0093(15) 0.0237(19) -0.0019(17) C6 0.0638(19) 0.0311(17) 0.064(2) 0.0059(14) 0.0180(16) 0.0040(15) C7 0.0456(16) 0.0244(15) 0.0536(17) 0.0006(12) 0.0122(14) 0.0024(12) C8 0.0534(18) 0.0318(16) 0.0568(18) 0.0039(13) 0.0179(15) -0.0004(13) C9 0.0510(19) 0.0387(19) 0.096(3) 0.0044(17) 0.0300(19) -0.0035(14) C10 0.0495(19) 0.048(2) 0.091(3) 0.0063(18) -0.0002(19) 0.0004(16) C11 0.065(2) 0.055(2) 0.066(2) 0.0034(17) -0.0028(19) 0.0038(18) C12 0.0579(19) 0.0435(19) 0.0506(18) 0.0008(14) 0.0130(15) 0.0042(14) C13 0.0419(15) 0.0291(15) 0.0488(16) 0.0040(12) 0.0146(13) -0.0027(12) C14 0.0504(17) 0.0329(16) 0.0455(16) -0.0002(12) 0.0110(14) -0.0024(13) C15 0.0520(18) 0.0439(19) 0.0547(18) 0.0040(14) 0.0051(15) -0.0047(15) C16 0.0403(16) 0.0480(19) 0.070(2) 0.0158(16) 0.0102(16) 0.0002(14) C17 0.0506(18) 0.0445(19) 0.064(2) 0.0045(15) 0.0260(16) 0.0020(14) C18 0.0513(17) 0.0387(17) 0.0444(15) -0.0008(13) 0.0177(13) -0.0089(13) C19 0.0471(16) 0.0370(17) 0.0377(14) -0.0023(12) 0.0157(13) -0.0023(13) C20 0.0440(16) 0.0360(16) 0.0395(15) -0.0023(12) 0.0176(13) -0.0048(13) C21 0.0452(16) 0.0438(18) 0.0395(15) 0.0030(13) 0.0074(13) -0.0019(13) C22 0.0566(18) 0.051(2) 0.0423(16) -0.0043(14) 0.0079(14) -0.0061(15) C23 0.062(2) 0.050(2) 0.0445(16) -0.0114(14) 0.0140(15) -0.0051(16) C24 0.0557(18) 0.0455(19) 0.0461(16) -0.0113(14) 0.0148(15) -0.0007(14) C25 0.0457(15) 0.0322(16) 0.0404(14) -0.0062(12) 0.0117(12) 0.0028(12) C26 0.0542(17) 0.0413(18) 0.0470(16) -0.0012(13) 0.0179(14) 0.0008(14) C27 0.0549(19) 0.062(2) 0.0577(19) -0.0083(16) 0.0204(15) 0.0131(16) C28 0.071(2) 0.040(2) 0.076(2) -0.0049(16) 0.0204(19) 0.0172(16) C29 0.074(2) 0.0329(18) 0.063(2) -0.0020(14) 0.0149(17) 0.0012(16) C30 0.0542(18) 0.0335(17) 0.0531(17) -0.0023(13) 0.0139(14) -0.0016(14) C31 0.0392(14) 0.0301(15) 0.0413(14) 0.0008(12) 0.0063(12) 0.0010(12) C32 0.0466(16) 0.0360(16) 0.0522(16) 0.0001(13) 0.0145(14) -0.0016(13) C33 0.0555(18) 0.047(2) 0.070(2) -0.0057(16) 0.0248(16) 0.0035(15) C34 0.066(2) 0.043(2) 0.084(2) 0.0021(18) 0.0174(19) 0.0151(16) C35 0.068(2) 0.0361(18) 0.075(2) 0.0132(16) 0.0160(18) 0.0061(16) C36 0.0485(16) 0.0426(18) 0.0464(16) 0.0023(13) 0.0120(13) 0.0005(14) C37 0.0414(14) 0.0286(15) 0.0355(14) 0.0032(11) 0.0088(12) -0.0005(12) C38 0.0431(15) 0.0301(15) 0.0398(14) 0.0056(11) 0.0130(12) -0.0010(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.403(3) . ? N1 C7 1.434(3) . ? N1 B1 1.434(4) . ? N2 C2 1.413(4) . ? N2 B1 1.440(4) . ? N2 C13 1.440(3) . ? N3 C19 1.406(3) . ? N3 C25 1.437(3) . ? N3 B2 1.447(4) . ? N4 C20 1.402(3) . ? N4 C31 1.434(3) . ? N4 B2 1.444(4) . ? B1 C37 1.601(4) . ? B2 C38 1.582(4) . ? B3 C38 1.711(4) . ? B3 C37 1.722(4) . ? B3 B8 1.767(4) . ? B3 B9 1.777(5) . ? B3 B4 1.778(4) . ? B3 H3 1.09(2) . ? B4 C37 1.725(4) . ? B4 B5 1.770(5) . ? B4 B9 1.771(5) . ? B4 B10 1.784(5) . ? B4 H4 1.09(3) . ? B5 C37 1.726(4) . ? B5 B11 1.761(5) . ? B5 B10 1.776(5) . ? B5 B6 1.779(5) . ? B5 H5 0.94(3) . ? B6 C37 1.726(4) . ? B6 C38 1.726(4) . ? B6 B11 1.771(5) . ? B6 B7 1.774(5) . ? B6 H6 1.09(3) . ? B7 C38 1.713(4) . ? B7 B8 1.768(5) . ? B7 B11 1.774(5) . ? B7 B12 1.783(5) . ? B7 H7 1.15(3) . ? B8 C38 1.727(4) . ? B8 B12 1.764(5) . ? B8 B9 1.778(5) . ? B8 H8 1.06(3) . ? B9 B10 1.777(5) . ? B9 B12 1.784(5) . ? B9 H9 1.15(4) . ? B10 B12 1.769(5) . ? B10 B11 1.774(5) . ? B10 H10 1.17(3) . ? B11 B12 1.783(5) . ? B11 H11 1.07(4) . ? B12 H12 1.16(3) . ? C1 C2 1.396(4) . ? C1 C6 1.397(4) . ? C2 C3 1.384(4) . ? C3 C4 1.376(5) . ? C3 H3A 0.9500 . ? C4 C5 1.395(5) . ? C4 H4A 0.9500 . ? C5 C6 1.376(5) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C12 1.377(4) . ? C7 C8 1.380(4) . ? C8 C9 1.377(4) . ? C8 H8A 0.9500 . ? C9 C10 1.365(5) . ? C9 H9A 0.9500 . ? C10 C11 1.381(5) . ? C10 H10A 0.9500 . ? C11 C12 1.382(4) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C13 C14 1.367(4) . ? C13 C18 1.405(4) . ? C14 C15 1.389(4) . ? C14 H14A 0.9500 . ? C15 C16 1.385(5) . ? C15 H15A 0.9500 . ? C16 C17 1.379(5) . ? C16 H16A 0.9500 . ? C17 C18 1.384(4) . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? C19 C24 1.390(4) . ? C19 C20 1.397(4) . ? C20 C21 1.383(4) . ? C21 C22 1.392(4) . ? C21 H21A 0.9500 . ? C22 C23 1.394(4) . ? C22 H22A 0.9500 . ? C23 C24 1.369(4) . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? C25 C30 1.378(4) . ? C25 C26 1.382(4) . ? C26 C27 1.395(4) . ? C26 H26A 0.9500 . ? C27 C28 1.377(5) . ? C27 H27A 0.9500 . ? C28 C29 1.389(5) . ? C28 H28A 0.9500 . ? C29 C30 1.380(4) . ? C29 H29A 0.9500 . ? C30 H30A 0.9500 . ? C31 C36 1.379(4) . ? C31 C32 1.391(4) . ? C32 C33 1.376(4) . ? C32 H32A 0.9500 . ? C33 C34 1.372(5) . ? C33 H33A 0.9500 . ? C34 C35 1.375(5) . ? C34 H34A 0.9500 . ? C35 C36 1.397(4) . ? C35 H35A 0.9500 . ? C36 H36A 0.9500 . ? C37 C38 1.697(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 C1 N1 C7 117.1(2) . . ? C1 N1 B1 108.2(2) . . ? C7 N1 B1 134.7(2) . . ? C2 N2 B1 108.0(2) . . ? C2 N2 C13 114.5(2) . . ? B1 N2 C13 137.5(2) . . ? C19 N3 C25 116.3(2) . . ? C19 N3 B2 108.0(2) . . ? C25 N3 B2 135.7(2) . . ? C20 N4 C31 117.4(2) . . ? C20 N4 B2 108.3(2) . . ? C31 N4 B2 134.3(2) . . ? N1 B1 N2 106.4(2) . . ? N1 B1 C37 125.1(2) . . ? N2 B1 C37 128.5(3) . . ? N4 B2 N3 105.9(2) . . ? N4 B2 C38 125.1(3) . . ? N3 B2 C38 128.9(2) . . ? C38 B3 C37 59.25(16) . . ? C38 B3 B8 59.53(17) . . ? C37 B3 B8 107.0(2) . . ? C38 B3 B9 106.8(2) . . ? C37 B3 B9 106.2(2) . . ? B8 B3 B9 60.23(18) . . ? C38 B3 B4 106.7(2) . . ? C37 B3 B4 59.03(17) . . ? B8 B3 B4 108.1(2) . . ? B9 B3 B4 59.74(18) . . ? C38 B3 H3 118.0(13) . . ? C37 B3 H3 118.0(13) . . ? B8 B3 H3 123.5(13) . . ? B9 B3 H3 128.2(13) . . ? B4 B3 H3 123.4(13) . . ? C37 B4 B5 59.19(17) . . ? C37 B4 B9 106.4(2) . . ? B5 B4 B9 108.1(2) . . ? C37 B4 B3 58.87(17) . . ? B5 B4 B3 107.4(2) . . ? B9 B4 B3 60.10(18) . . ? C37 B4 B10 106.0(2) . . ? B5 B4 B10 59.96(19) . . ? B9 B4 B10 59.99(19) . . ? B3 B4 B10 107.5(2) . . ? C37 B4 H4 111.9(16) . . ? B5 B4 H4 118.2(16) . . ? B9 B4 H4 130.3(16) . . ? B3 B4 H4 117.0(15) . . ? B10 B4 H4 131.9(15) . . ? C37 B5 B11 106.0(2) . . ? C37 B5 B4 59.13(17) . . ? B11 B5 B4 108.4(2) . . ? C37 B5 B10 106.3(2) . . ? B11 B5 B10 60.23(19) . . ? B4 B5 B10 60.42(19) . . ? C37 B5 B6 58.97(16) . . ? B11 B5 B6 60.05(19) . . ? B4 B5 B6 107.9(2) . . ? B10 B5 B6 108.3(2) . . ? C37 B5 H5 116(2) . . ? B11 B5 H5 124(2) . . ? B4 B5 H5 124(2) . . ? B10 B5 H5 131(2) . . ? B6 B5 H5 114(2) . . ? C37 B6 C38 58.91(16) . . ? C37 B6 B11 105.5(2) . . ? C38 B6 B11 105.5(2) . . ? C37 B6 B7 106.0(2) . . ? C38 B6 B7 58.59(17) . . ? B11 B6 B7 60.06(19) . . ? C37 B6 B5 58.98(17) . . ? C38 B6 B5 105.9(2) . . ? B11 B6 B5 59.46(19) . . ? B7 B6 B5 107.6(2) . . ? C37 B6 H6 120.1(15) . . ? C38 B6 H6 122.0(14) . . ? B11 B6 H6 125.8(14) . . ? B7 B6 H6 124.5(15) . . ? B5 B6 H6 121.6(14) . . ? C38 B7 B8 59.47(17) . . ? C38 B7 B6 59.30(17) . . ? B8 B7 B6 108.3(2) . . ? C38 B7 B11 105.9(2) . . ? B8 B7 B11 107.7(2) . . ? B6 B7 B11 59.91(18) . . ? C38 B7 B12 106.0(2) . . ? B8 B7 B12 59.56(18) . . ? B6 B7 B12 108.2(2) . . ? B11 B7 B12 60.15(19) . . ? C38 B7 H7 116.9(13) . . ? B8 B7 H7 117.8(13) . . ? B6 B7 H7 120.7(14) . . ? B11 B7 H7 128.5(13) . . ? B12 B7 H7 126.2(14) . . ? C38 B8 B12 106.2(2) . . ? C38 B8 B3 58.64(17) . . ? B12 B8 B3 108.3(2) . . ? C38 B8 B7 58.67(17) . . ? B12 B8 B7 60.65(19) . . ? B3 B8 B7 107.3(2) . . ? C38 B8 B9 106.0(2) . . ? B12 B8 B9 60.48(18) . . ? B3 B8 B9 60.19(18) . . ? B7 B8 B9 108.7(2) . . ? C38 B8 H8 120.4(15) . . ? B12 B8 H8 126.1(15) . . ? B3 B8 H8 117.9(15) . . ? B7 B8 H8 123.2(15) . . ? B9 B8 H8 122.5(15) . . ? B4 B9 B8 107.9(2) . . ? B4 B9 B3 60.16(18) . . ? B8 B9 B3 59.58(17) . . ? B4 B9 B10 60.36(19) . . ? B8 B9 B10 107.2(2) . . ? B3 B9 B10 107.8(2) . . ? B4 B9 B12 107.8(2) . . ? B8 B9 B12 59.36(18) . . ? B3 B9 B12 106.9(2) . . ? B10 B9 B12 59.58(19) . . ? B4 B9 H9 122.1(18) . . ? B8 B9 H9 121.0(17) . . ? B3 B9 H9 121.3(17) . . ? B10 B9 H9 123.1(17) . . ? B12 B9 H9 122.4(18) . . ? B12 B10 B11 60.41(19) . . ? B12 B10 B5 108.0(2) . . ? B11 B10 B5 59.47(19) . . ? B12 B10 B9 60.40(19) . . ? B11 B10 B9 108.2(2) . . ? B5 B10 B9 107.6(2) . . ? B12 B10 B4 107.9(2) . . ? B11 B10 B4 107.2(2) . . ? B5 B10 B4 59.63(19) . . ? B9 B10 B4 59.64(18) . . ? B12 B10 H10 123.9(14) . . ? B11 B10 H10 122.6(13) . . ? B5 B10 H10 120.0(14) . . ? B9 B10 H10 122.4(13) . . ? B4 B10 H10 120.2(14) . . ? B5 B11 B6 60.50(18) . . ? B5 B11 B10 60.30(19) . . ? B6 B11 B10 108.7(2) . . ? B5 B11 B7 108.4(2) . . ? B6 B11 B7 60.03(18) . . ? B10 B11 B7 108.1(2) . . ? B5 B11 B12 108.1(2) . . ? B6 B11 B12 108.3(2) . . ? B10 B11 B12 59.65(19) . . ? B7 B11 B12 60.18(18) . . ? B5 B11 H11 128(2) . . ? B6 B11 H11 117(2) . . ? B10 B11 H11 130(2) . . ? B7 B11 H11 112(2) . . ? B12 B11 H11 119(2) . . ? B8 B12 B10 108.2(2) . . ? B8 B12 B11 107.5(2) . . ? B10 B12 B11 59.94(19) . . ? B8 B12 B7 59.79(18) . . ? B10 B12 B7 107.9(2) . . ? B11 B12 B7 59.67(19) . . ? B8 B12 B9 60.16(18) . . ? B10 B12 B9 60.02(19) . . ? B11 B12 B9 107.6(2) . . ? B7 B12 B9 107.8(2) . . ? B8 B12 H12 119.4(12) . . ? B10 B12 H12 123.1(12) . . ? B11 B12 H12 124.3(12) . . ? B7 B12 H12 121.7(13) . . ? B9 B12 H12 120.6(13) . . ? C2 C1 C6 120.8(3) . . ? C2 C1 N1 109.1(2) . . ? C6 C1 N1 130.2(3) . . ? C3 C2 C1 121.0(3) . . ? C3 C2 N2 130.6(3) . . ? C1 C2 N2 108.4(2) . . ? C4 C3 C2 118.2(3) . . ? C4 C3 H3A 120.9 . . ? C2 C3 H3A 120.9 . . ? C3 C4 C5 120.9(3) . . ? C3 C4 H4A 119.6 . . ? C5 C4 H4A 119.6 . . ? C6 C5 C4 121.7(3) . . ? C6 C5 H5A 119.1 . . ? C4 C5 H5A 119.1 . . ? C5 C6 C1 117.5(3) . . ? C5 C6 H6A 121.3 . . ? C1 C6 H6A 121.3 . . ? C12 C7 C8 119.6(3) . . ? C12 C7 N1 119.2(3) . . ? C8 C7 N1 121.2(3) . . ? C9 C8 C7 120.1(3) . . ? C9 C8 H8A 119.9 . . ? C7 C8 H8A 119.9 . . ? C10 C9 C8 120.4(3) . . ? C10 C9 H9A 119.8 . . ? C8 C9 H9A 119.8 . . ? C9 C10 C11 119.8(3) . . ? C9 C10 H10A 120.1 . . ? C11 C10 H10A 120.1 . . ? C12 C11 C10 120.0(3) . . ? C12 C11 H11A 120.0 . . ? C10 C11 H11A 120.0 . . ? C7 C12 C11 120.0(3) . . ? C7 C12 H12A 120.0 . . ? C11 C12 H12A 120.0 . . ? C14 C13 C18 120.0(3) . . ? C14 C13 N2 119.9(2) . . ? C18 C13 N2 119.4(2) . . ? C13 C14 C15 120.9(3) . . ? C13 C14 H14A 119.5 . . ? C15 C14 H14A 119.5 . . ? C16 C15 C14 119.4(3) . . ? C16 C15 H15A 120.3 . . ? C14 C15 H15A 120.3 . . ? C17 C16 C15 119.9(3) . . ? C17 C16 H16A 120.0 . . ? C15 C16 H16A 120.0 . . ? C16 C17 C18 121.0(3) . . ? C16 C17 H17A 119.5 . . ? C18 C17 H17A 119.5 . . ? C17 C18 C13 118.7(3) . . ? C17 C18 H18A 120.6 . . ? C13 C18 H18A 120.6 . . ? C24 C19 C20 121.2(3) . . ? C24 C19 N3 129.8(3) . . ? C20 C19 N3 109.0(2) . . ? C21 C20 C19 120.7(3) . . ? C21 C20 N4 130.3(3) . . ? C19 C20 N4 108.9(2) . . ? C20 C21 C22 118.1(3) . . ? C20 C21 H21A 121.0 . . ? C22 C21 H21A 121.0 . . ? C21 C22 C23 120.3(3) . . ? C21 C22 H22A 119.8 . . ? C23 C22 H22A 119.8 . . ? C24 C23 C22 122.1(3) . . ? C24 C23 H23A 119.0 . . ? C22 C23 H23A 119.0 . . ? C23 C24 C19 117.5(3) . . ? C23 C24 H24A 121.3 . . ? C19 C24 H24A 121.3 . . ? C30 C25 C26 120.4(3) . . ? C30 C25 N3 119.1(2) . . ? C26 C25 N3 120.1(3) . . ? C25 C26 C27 119.3(3) . . ? C25 C26 H26A 120.4 . . ? C27 C26 H26A 120.4 . . ? C28 C27 C26 120.1(3) . . ? C28 C27 H27A 119.9 . . ? C26 C27 H27A 119.9 . . ? C27 C28 C29 120.3(3) . . ? C27 C28 H28A 119.9 . . ? C29 C28 H28A 119.9 . . ? C30 C29 C28 119.4(3) . . ? C30 C29 H29A 120.3 . . ? C28 C29 H29A 120.3 . . ? C25 C30 C29 120.5(3) . . ? C25 C30 H30A 119.7 . . ? C29 C30 H30A 119.7 . . ? C36 C31 C32 119.8(3) . . ? C36 C31 N4 119.7(2) . . ? C32 C31 N4 120.5(2) . . ? C33 C32 C31 120.0(3) . . ? C33 C32 H32A 120.0 . . ? C31 C32 H32A 120.0 . . ? C34 C33 C32 120.4(3) . . ? C34 C33 H33A 119.8 . . ? C32 C33 H33A 119.8 . . ? C33 C34 C35 120.1(3) . . ? C33 C34 H34A 119.9 . . ? C35 C34 H34A 119.9 . . ? C34 C35 C36 120.1(3) . . ? C34 C35 H35A 120.0 . . ? C36 C35 H35A 120.0 . . ? C31 C36 C35 119.5(3) . . ? C31 C36 H36A 120.2 . . ? C35 C36 H36A 120.2 . . ? B1 C37 C38 121.0(2) . . ? B1 C37 B3 118.9(2) . . ? C38 C37 B3 60.04(16) . . ? B1 C37 B4 119.9(2) . . ? C38 C37 B4 109.8(2) . . ? B3 C37 B4 62.10(17) . . ? B1 C37 B6 119.1(2) . . ? C38 C37 B6 60.53(16) . . ? B3 C37 B6 111.4(2) . . ? B4 C37 B6 112.5(2) . . ? B1 C37 B5 120.6(2) . . ? C38 C37 B5 109.6(2) . . ? B3 C37 B5 112.0(2) . . ? B4 C37 B5 61.68(18) . . ? B6 C37 B5 62.04(18) . . ? B2 C38 C37 122.8(2) . . ? B2 C38 B3 119.8(2) . . ? C37 C38 B3 60.71(16) . . ? B2 C38 B7 118.1(2) . . ? C37 C38 B7 110.1(2) . . ? B3 C38 B7 112.5(2) . . ? B2 C38 B6 119.2(2) . . ? C37 C38 B6 60.56(16) . . ? B3 C38 B6 112.0(2) . . ? B7 C38 B6 62.11(18) . . ? B2 C38 B8 118.7(2) . . ? C37 C38 B8 109.9(2) . . ? B3 C38 B8 61.84(17) . . ? B7 C38 B8 61.86(18) . . ? B6 C38 B8 112.5(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.416 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.091 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound18 _database_code_depnum_ccdc_archive 'CCDC 847436' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H38 B12 N4' _chemical_formula_sum 'C22 H38 B12 N4' _chemical_formula_weight 488.28 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' 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.41830(10) _cell_length_b 8.89920(10) _cell_length_c 17.30630(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.6578(4) _cell_angle_gamma 90.00 _cell_volume 2681.51(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 92651 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description irregular _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9808 _exptl_absorpt_correction_T_max 0.9808 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 67508 _diffrn_reflns_av_R_equivalents 0.025 _diffrn_reflns_av_sigmaI/netI 0.0128 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3906 _reflns_number_gt 3675 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+1.5248P] 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 3906 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0397 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.1056 _refine_ls_wR_factor_gt 0.1042 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 N1 N 0.33853(4) 0.06593(7) 0.35952(4) 0.01384(13) Uani 1 1 d . . . N2 N 0.40264(4) 0.19581(7) 0.45691(4) 0.01392(13) Uani 1 1 d . . . B1 B 0.40207(5) 0.16555(9) 0.37515(5) 0.01297(16) Uani 1 1 d . . . B2 B 0.54079(5) 0.17592(9) 0.28168(5) 0.01364(16) Uani 1 1 d . . . H2 H 0.5619(7) 0.0702(13) 0.2990(7) 0.020(3) Uiso 1 1 d . . . B3 B 0.53793(5) 0.33646(10) 0.34089(5) 0.01649(17) Uani 1 1 d . . . H3 H 0.5599(7) 0.3272(13) 0.3987(7) 0.024(3) Uiso 1 1 d . . . B4 B 0.45237(5) 0.43741(10) 0.31581(5) 0.01767(17) Uani 1 1 d . . . H4 H 0.4169(7) 0.4922(14) 0.3602(7) 0.026(3) Uiso 1 1 d . . . B5 B 0.40367(5) 0.33616(10) 0.24056(5) 0.01614(17) Uani 1 1 d . . . H5 H 0.3428(7) 0.3273(13) 0.2384(7) 0.024(3) Uiso 1 1 d . . . B6 B 0.45809(6) 0.49934(10) 0.21865(5) 0.02058(18) Uani 1 1 d . . . H6 H 0.4313(7) 0.6024(15) 0.1973(7) 0.030(3) Uiso 1 1 d . . . C1 C 0.30274(4) 0.03727(9) 0.42928(4) 0.01440(15) Uani 1 1 d . . . C2 C 0.34170(4) 0.11652(9) 0.48850(4) 0.01463(15) Uani 1 1 d . . . C3 C 0.31659(5) 0.11187(10) 0.56417(4) 0.01861(16) Uani 1 1 d . . . H3A H 0.3430 0.1651 0.6044 0.022 Uiso 1 1 calc R . . C4 C 0.25147(5) 0.02672(10) 0.57913(5) 0.02063(17) Uani 1 1 d . . . H4A H 0.2330 0.0229 0.6302 0.025 Uiso 1 1 calc R . . C5 C 0.21293(5) -0.05300(10) 0.52028(5) 0.02013(17) Uani 1 1 d . . . H5A H 0.1689 -0.1108 0.5320 0.024 Uiso 1 1 calc R . . C6 C 0.23815(4) -0.04899(9) 0.44437(5) 0.01762(16) Uani 1 1 d . . . H6A H 0.2121 -0.1034 0.4043 0.021 Uiso 1 1 calc R . . C7 C 0.30679(4) -0.00224(9) 0.28887(4) 0.01522(15) Uani 1 1 d . . . H7A H 0.3240 0.0557 0.2437 0.018 Uiso 1 1 calc R . . H7B H 0.2500 0.0030 0.2893 0.018 Uiso 1 1 calc R . . C8 C 0.33141(5) -0.16599(9) 0.28040(5) 0.02003(16) Uani 1 1 d . . . H8A H 0.3872 -0.1709 0.2750 0.030 Uiso 1 1 calc R . . H8B H 0.3059 -0.2096 0.2345 0.030 Uiso 1 1 calc R . . H8C H 0.3170 -0.2226 0.3263 0.030 Uiso 1 1 calc R . . C9 C 0.45047(4) 0.28930(9) 0.50857(4) 0.01581(15) Uani 1 1 d . . . H9A H 0.4175 0.3386 0.5467 0.019 Uiso 1 1 calc R . . H9B H 0.4751 0.3690 0.4780 0.019 Uiso 1 1 calc R . . C10 C 0.51258(5) 0.19790(10) 0.55141(5) 0.02233(17) Uani 1 1 d . . . H10A H 0.4886 0.1161 0.5799 0.034 Uiso 1 1 calc R . . H10B H 0.5410 0.2632 0.5877 0.034 Uiso 1 1 calc R . . H10C H 0.5480 0.1558 0.5141 0.034 Uiso 1 1 calc R . . C11 C 0.45468(4) 0.24309(8) 0.31239(4) 0.01266(14) 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 N1 0.0135(3) 0.0164(3) 0.0117(3) -0.0007(2) 0.0016(2) -0.0019(2) N2 0.0132(3) 0.0163(3) 0.0123(3) -0.0008(2) 0.0015(2) -0.0022(2) B1 0.0121(3) 0.0141(3) 0.0127(3) 0.0001(3) 0.0009(3) 0.0000(3) B2 0.0117(3) 0.0165(4) 0.0128(3) 0.0002(3) 0.0009(3) 0.0001(3) B3 0.0153(4) 0.0194(4) 0.0149(4) -0.0030(3) 0.0024(3) -0.0043(3) B4 0.0211(4) 0.0141(4) 0.0182(4) -0.0006(3) 0.0064(3) 0.0001(3) B5 0.0148(4) 0.0186(4) 0.0151(4) 0.0025(3) 0.0028(3) 0.0041(3) B6 0.0258(4) 0.0156(4) 0.0208(4) 0.0032(3) 0.0092(3) 0.0047(3) C1 0.0140(3) 0.0160(3) 0.0133(3) 0.0007(2) 0.0023(2) -0.0003(2) C2 0.0136(3) 0.0161(3) 0.0143(3) 0.0006(3) 0.0018(2) -0.0010(2) C3 0.0182(3) 0.0240(4) 0.0137(3) -0.0002(3) 0.0021(3) -0.0022(3) C4 0.0198(4) 0.0276(4) 0.0148(3) 0.0023(3) 0.0048(3) -0.0022(3) C5 0.0172(3) 0.0241(4) 0.0194(4) 0.0028(3) 0.0047(3) -0.0042(3) C6 0.0159(3) 0.0197(4) 0.0174(3) -0.0003(3) 0.0022(3) -0.0038(3) C7 0.0141(3) 0.0178(3) 0.0137(3) -0.0015(3) -0.0003(2) -0.0024(2) C8 0.0228(4) 0.0178(4) 0.0194(4) -0.0048(3) 0.0004(3) -0.0004(3) C9 0.0169(3) 0.0173(3) 0.0133(3) -0.0027(3) 0.0001(2) -0.0027(3) C10 0.0208(4) 0.0241(4) 0.0217(4) -0.0020(3) -0.0062(3) -0.0015(3) C11 0.0117(3) 0.0140(3) 0.0124(3) -0.0004(2) 0.0010(2) -0.0004(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 N1 C1 1.3981(9) . ? N1 B1 1.4377(10) . ? N1 C7 1.4592(9) . ? N2 C2 1.3990(9) . ? N2 B1 1.4400(10) . ? N2 C9 1.4637(9) . ? B1 C11 1.5978(11) . ? B2 C11 1.7134(11) . ? B2 C11 1.7383(11) 2_655 ? B2 B3 1.7597(12) . ? B2 B2 1.7697(16) 2_655 ? B2 B5 1.7718(12) 2_655 ? B2 H2 1.051(12) . ? B3 C11 1.7306(11) . ? B3 B5 1.7621(12) 2_655 ? B3 B6 1.7809(13) 2_655 ? B3 B4 1.7830(13) . ? B3 H3 1.064(12) . ? B4 C11 1.7308(12) . ? B4 B6 1.7737(13) 2_655 ? B4 B6 1.7751(13) . ? B4 B5 1.7787(13) . ? B4 H4 1.113(13) . ? B5 C11 1.7197(11) . ? B5 B3 1.7620(12) 2_655 ? B5 B2 1.7718(12) 2_655 ? B5 B6 1.7810(13) . ? B5 H5 1.063(12) . ? B6 B4 1.7737(13) 2_655 ? B6 B3 1.7810(13) 2_655 ? B6 B6 1.794(2) 2_655 ? B6 H6 1.088(13) . ? C1 C6 1.3929(10) . ? C1 C2 1.4030(10) . ? C2 C3 1.3932(10) . ? C3 C4 1.3947(11) . ? C3 H3A 0.9500 . ? C4 C5 1.3971(12) . ? C4 H4A 0.9500 . ? C5 C6 1.3977(11) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C8 1.5273(11) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.5282(11) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 B2 1.7383(11) 2_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 B1 108.06(6) . . ? C1 N1 C7 118.69(6) . . ? B1 N1 C7 133.23(6) . . ? C2 N2 B1 107.82(6) . . ? C2 N2 C9 118.22(6) . . ? B1 N2 C9 133.95(6) . . ? N1 B1 N2 106.48(6) . . ? N1 B1 C11 126.30(6) . . ? N2 B1 C11 126.82(7) . . ? C11 B2 C11 103.55(6) . 2_655 ? C11 B2 B3 59.75(5) . . ? C11 B2 B3 105.61(6) 2_655 . ? C11 B2 B2 59.85(5) . 2_655 ? C11 B2 B2 58.46(5) 2_655 2_655 ? B3 B2 B2 108.97(5) . 2_655 ? C11 B2 B5 105.96(6) . 2_655 ? C11 B2 B5 58.66(5) 2_655 2_655 ? B3 B2 B5 59.86(5) . 2_655 ? B2 B2 B5 107.40(5) 2_655 2_655 ? C11 B2 H2 121.7(6) . . ? C11 B2 H2 123.4(6) 2_655 . ? B3 B2 H2 125.2(6) . . ? B2 B2 H2 116.4(6) 2_655 . ? B5 B2 H2 126.5(6) 2_655 . ? C11 B3 B2 58.79(4) . . ? C11 B3 B5 105.64(6) . 2_655 ? B2 B3 B5 60.41(5) . 2_655 ? C11 B3 B6 105.80(6) . 2_655 ? B2 B3 B6 108.76(6) . 2_655 ? B5 B3 B6 60.35(5) 2_655 2_655 ? C11 B3 B4 59.00(5) . . ? B2 B3 B4 107.75(6) . . ? B5 B3 B4 107.69(6) 2_655 . ? B6 B3 B4 59.69(5) 2_655 . ? C11 B3 H3 120.4(7) . . ? B2 B3 H3 118.0(7) . . ? B5 B3 H3 123.5(7) 2_655 . ? B6 B3 H3 126.0(7) 2_655 . ? B4 B3 H3 122.9(7) . . ? C11 B4 B6 106.10(6) . 2_655 ? C11 B4 B6 106.01(6) . . ? B6 B4 B6 60.72(6) 2_655 . ? C11 B4 B5 58.66(5) . . ? B6 B4 B5 108.46(6) 2_655 . ? B6 B4 B5 60.15(5) . . ? C11 B4 B3 58.99(5) . . ? B6 B4 B3 60.10(5) 2_655 . ? B6 B4 B3 108.52(6) . . ? B5 B4 B3 107.49(6) . . ? C11 B4 H4 118.4(7) . . ? B6 B4 H4 127.4(7) 2_655 . ? B6 B4 H4 124.5(6) . . ? B5 B4 H4 117.7(6) . . ? B3 B4 H4 122.0(6) . . ? C11 B5 B3 106.31(6) . 2_655 ? C11 B5 B2 59.70(4) . 2_655 ? B3 B5 B2 59.73(5) 2_655 2_655 ? C11 B5 B4 59.28(5) . . ? B3 B5 B4 108.11(6) 2_655 . ? B2 B5 B4 108.36(6) 2_655 . ? C11 B5 B6 106.23(6) . . ? B3 B5 B6 60.35(5) 2_655 . ? B2 B5 B6 108.22(6) 2_655 . ? B4 B5 B6 59.82(5) . . ? C11 B5 H5 118.9(7) . . ? B3 B5 H5 124.8(7) 2_655 . ? B2 B5 H5 118.9(7) 2_655 . ? B4 B5 H5 121.1(7) . . ? B6 B5 H5 126.2(7) . . ? B4 B6 B4 107.22(6) 2_655 . ? B4 B6 B3 60.21(5) 2_655 2_655 ? B4 B6 B3 107.43(6) . 2_655 ? B4 B6 B5 107.27(6) 2_655 . ? B4 B6 B5 60.02(5) . . ? B3 B6 B5 59.30(5) 2_655 . ? B4 B6 B6 59.68(6) 2_655 2_655 ? B4 B6 B6 59.60(6) . 2_655 ? B3 B6 B6 107.78(5) 2_655 2_655 ? B5 B6 B6 107.47(5) . 2_655 ? B4 B6 H6 121.3(7) 2_655 . ? B4 B6 H6 123.2(7) . . ? B3 B6 H6 120.9(7) 2_655 . ? B5 B6 H6 122.3(7) . . ? B6 B6 H6 122.6(7) 2_655 . ? C6 C1 N1 130.18(7) . . ? C6 C1 C2 121.09(7) . . ? N1 C1 C2 108.71(6) . . ? C3 C2 N2 130.14(7) . . ? C3 C2 C1 120.89(7) . . ? N2 C2 C1 108.93(6) . . ? C2 C3 C4 118.02(7) . . ? C2 C3 H3A 121.0 . . ? C4 C3 H3A 121.0 . . ? C3 C4 C5 121.11(7) . . ? C3 C4 H4A 119.4 . . ? C5 C4 H4A 119.4 . . ? C4 C5 C6 120.98(7) . . ? C4 C5 H5A 119.5 . . ? C6 C5 H5A 119.5 . . ? C1 C6 C5 117.90(7) . . ? C1 C6 H6A 121.1 . . ? C5 C6 H6A 121.1 . . ? N1 C7 C8 112.12(6) . . ? N1 C7 H7A 109.2 . . ? C8 C7 H7A 109.2 . . ? N1 C7 H7B 109.2 . . ? C8 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? 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 . . ? N2 C9 C10 112.10(7) . . ? N2 C9 H9A 109.2 . . ? C10 C9 H9A 109.2 . . ? N2 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? B1 C11 B2 125.77(6) . . ? B1 C11 B5 113.88(6) . . ? B2 C11 B5 112.49(5) . . ? B1 C11 B3 120.39(6) . . ? B2 C11 B3 61.45(5) . . ? B5 C11 B3 112.70(6) . . ? B1 C11 B4 113.20(6) . . ? B2 C11 B4 112.37(6) . . ? B5 C11 B4 62.06(5) . . ? B3 C11 B4 62.01(5) . . ? B1 C11 B2 122.04(6) . 2_655 ? B2 C11 B2 61.68(5) . 2_655 ? B5 C11 B2 61.64(5) . 2_655 ? B3 C11 B2 111.82(5) . 2_655 ? B4 C11 B2 112.17(6) . 2_655 ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.388 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.042 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound19 _database_code_depnum_ccdc_archive 'CCDC 847437' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H38 B12 N4' _chemical_formula_sum 'C38 H38 B12 N4' _chemical_formula_weight 680.44 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.0270(8) _cell_length_b 11.1965(6) _cell_length_c 19.2084(10) _cell_angle_alpha 90.00 _cell_angle_beta 100.629(3) _cell_angle_gamma 90.00 _cell_volume 3599.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6644 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 25.028 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.256 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9877 _exptl_absorpt_correction_T_max 0.9932 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11323 _diffrn_reflns_av_R_equivalents 0.049 _diffrn_reflns_av_sigmaI/netI 0.0535 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3164 _reflns_number_gt 2252 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+2.3146P] 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 SHELXL _refine_ls_extinction_coef 0.0052(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3164 _refine_ls_number_parameters 238 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0777 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1248 _refine_ls_wR_factor_gt 0.1110 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 N1 N 0.14045(9) 0.49858(14) 0.16019(8) 0.0326(4) Uani 1 1 d . . . N2 N 0.09218(9) 0.63149(14) 0.07138(8) 0.0308(4) Uani 1 1 d . . . C1 C 0.17948(11) 0.4782(2) 0.10288(10) 0.0376(5) Uani 1 1 d . A . C2 C 0.14955(11) 0.55719(18) 0.04893(10) 0.0356(5) Uani 1 1 d . A . C3 C 0.17432(13) 0.5525(2) -0.01607(11) 0.0464(6) Uani 1 1 d . . . H3A H 0.1527 0.6048 -0.0537 0.056 Uiso 1 1 calc R A . C4 C 0.23173(14) 0.4684(3) -0.02370(13) 0.0608(7) Uani 1 1 d . A . H4A H 0.2498 0.4629 -0.0675 0.073 Uiso 1 1 calc R . . C5 C 0.26322(15) 0.3925(3) 0.03072(13) 0.0701(9) Uani 1 1 d . . . H5A H 0.3035 0.3371 0.0241 0.084 Uiso 1 1 calc R A . C6 C 0.23719(13) 0.3953(2) 0.09508(12) 0.0551(7) Uani 1 1 d . A . H6A H 0.2583 0.3421 0.1324 0.066 Uiso 1 1 calc R . . C7A C 0.15261(13) 0.4114(2) 0.21962(6) 0.031(2) Uiso 0.427(4) 1 d PG A 1 C8A C 0.22374(12) 0.4135(4) 0.26860(8) 0.0289(12) Uiso 0.427(4) 1 d PG A 1 H8A H 0.2633 0.4716 0.2646 0.035 Uiso 0.427(4) 1 calc PR A 1 C9A C 0.23692(19) 0.3306(4) 0.32338(8) 0.0243(11) Uiso 0.427(4) 1 d PG A 1 H9A H 0.2855 0.3320 0.3569 0.029 Uiso 0.427(4) 1 calc PR A 1 C10A C 0.1790(3) 0.2456(3) 0.32919(9) 0.0270(11) Uiso 0.427(4) 1 d PG A 1 H10A H 0.1880 0.1889 0.3666 0.032 Uiso 0.427(4) 1 calc PR A 1 C11A C 0.1078(3) 0.24350(17) 0.28022(10) 0.0285(11) Uiso 0.427(4) 1 d PG A 1 H11A H 0.0682 0.1854 0.2842 0.034 Uiso 0.427(4) 1 calc PR A 1 C12A C 0.09466(19) 0.32639(16) 0.22543(8) 0.0317(17) Uiso 0.427(4) 1 d PG A 1 H12A H 0.0460 0.3250 0.1920 0.038 Uiso 0.427(4) 1 calc PR A 1 C7B C 0.16255(12) 0.4347(2) 0.21938(7) 0.0238(16) Uiso 0.415(6) 1 d PG A 2 C8B C 0.23087(10) 0.4574(4) 0.26948(9) 0.0289(12) Uiso 0.415(6) 1 d PG A 2 H8B H 0.2629 0.5253 0.2646 0.035 Uiso 0.415(6) 1 calc PR A 2 C9B C 0.25239(14) 0.3807(5) 0.32672(8) 0.0321(13) Uiso 0.415(6) 1 d PG A 2 H9B H 0.2991 0.3962 0.3610 0.039 Uiso 0.415(6) 1 calc PR A 2 C10B C 0.2056(2) 0.2814(4) 0.33387(8) 0.0284(13) Uiso 0.415(6) 1 d PG A 2 H10B H 0.2203 0.2290 0.3730 0.034 Uiso 0.415(6) 1 calc PR A 2 C11B C 0.1373(3) 0.2587(2) 0.28376(9) 0.0330(12) Uiso 0.415(6) 1 d PG A 2 H11B H 0.1053 0.1908 0.2886 0.040 Uiso 0.415(6) 1 calc PR A 2 C12B C 0.11576(19) 0.33534(17) 0.22653(7) 0.0275(13) Uiso 0.415(6) 1 d PG A 2 H12B H 0.0691 0.3198 0.1923 0.033 Uiso 0.415(6) 1 calc PR A 2 C7C C 0.14396(14) 0.3964(2) 0.21799(6) 0.015(4) Uiso 0.158(6) 1 d PG A 3 C8C C 0.21406(14) 0.3839(4) 0.26752(7) 0.032(4) Uiso 0.158(6) 1 d PG A 3 H8C H 0.2579 0.4358 0.2662 0.039 Uiso 0.158(6) 1 calc PR A 3 C9C C 0.2200(2) 0.2955(4) 0.31902(8) 0.028(3) Uiso 0.158(6) 1 d PG A 3 H9C H 0.2680 0.2869 0.3529 0.034 Uiso 0.158(6) 1 calc PR A 3 C10C C 0.1559(3) 0.2196(3) 0.32099(10) 0.025(3) Uiso 0.158(6) 1 d PG A 3 H10C H 0.1600 0.1591 0.3562 0.029 Uiso 0.158(6) 1 calc PR A 3 C11C C 0.0858(3) 0.23206(16) 0.27147(11) 0.039(4) Uiso 0.158(6) 1 d PG A 3 H11C H 0.0420 0.1802 0.2728 0.047 Uiso 0.158(6) 1 calc PR A 3 C12C C 0.0798(2) 0.32047(16) 0.21997(9) 0.027(4) Uiso 0.158(6) 1 d PG A 3 H12C H 0.0319 0.3290 0.1861 0.032 Uiso 0.158(6) 1 calc PR A 3 C13 C 0.05347(12) 0.72012(17) 0.02255(10) 0.0348(5) Uani 1 1 d . A . C14 C -0.02538(13) 0.7065(2) -0.00949(10) 0.0410(5) Uani 1 1 d . . . H14A H -0.0553 0.6401 0.0019 0.049 Uiso 1 1 calc R A . C15 C -0.06079(17) 0.7904(2) -0.05849(12) 0.0569(7) Uani 1 1 d . A . H15A H -0.1156 0.7826 -0.0796 0.068 Uiso 1 1 calc R . . C16 C -0.0170(2) 0.8850(2) -0.07672(12) 0.0735(9) Uani 1 1 d . . . H16A H -0.0412 0.9414 -0.1110 0.088 Uiso 1 1 calc R A . C17 C 0.0613(2) 0.8975(2) -0.04541(12) 0.0732(9) Uani 1 1 d . A . H17A H 0.0912 0.9633 -0.0578 0.088 Uiso 1 1 calc R . . C18 C 0.09774(16) 0.8153(2) 0.00421(11) 0.0515(6) Uani 1 1 d . . . H18A H 0.1524 0.8240 0.0254 0.062 Uiso 1 1 calc R A . C19 C 0.03989(10) 0.66360(16) 0.19551(9) 0.0273(4) Uani 1 1 d . . . B1 B 0.08617(12) 0.5966(2) 0.14243(11) 0.0291(5) Uani 1 1 d . A . B2 B 0.04569(12) 0.6110(2) 0.28140(11) 0.0277(5) Uani 1 1 d . . . H2 H 0.0700(10) 0.5270(17) 0.2995(9) 0.027(5) Uiso 1 1 d . . . B3 B 0.04846(13) 0.7388(2) 0.33488(12) 0.0317(5) Uani 1 1 d . . . H3 H 0.0782(10) 0.7313(16) 0.3905(10) 0.033(5) Uiso 1 1 d . . . B4 B 0.04655(14) 0.8675(2) 0.28062(13) 0.0366(6) Uani 1 1 d . . . H4 H 0.0786(11) 0.9506(18) 0.3003(10) 0.039(5) Uiso 1 1 d . . . B5 B 0.04204(13) 0.8179(2) 0.19239(12) 0.0330(5) Uani 1 1 d . . . H5 H 0.0720(11) 0.8599(17) 0.1528(10) 0.037(5) Uiso 1 1 d . . . B6 B 0.10061(13) 0.7379(2) 0.26361(11) 0.0303(5) Uani 1 1 d . A . H6 H 0.1665(11) 0.7302(16) 0.2690(9) 0.030(5) Uiso 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 N1 0.0333(9) 0.0403(10) 0.0255(9) -0.0037(8) 0.0091(7) 0.0020(8) N2 0.0384(9) 0.0303(9) 0.0266(9) -0.0043(7) 0.0134(7) -0.0070(7) C1 0.0353(11) 0.0511(13) 0.0289(11) -0.0097(10) 0.0123(9) -0.0021(10) C2 0.0364(11) 0.0437(12) 0.0302(11) -0.0102(10) 0.0152(9) -0.0104(9) C3 0.0522(13) 0.0564(14) 0.0352(13) -0.0070(11) 0.0199(10) -0.0096(11) C4 0.0600(15) 0.090(2) 0.0397(14) -0.0129(14) 0.0294(12) 0.0033(14) C5 0.0614(16) 0.109(2) 0.0448(15) -0.0149(16) 0.0237(12) 0.0288(16) C6 0.0481(13) 0.0815(18) 0.0368(13) -0.0102(12) 0.0110(10) 0.0218(13) C13 0.0559(13) 0.0299(11) 0.0203(10) -0.0018(9) 0.0118(9) -0.0074(9) C14 0.0577(14) 0.0425(12) 0.0239(11) -0.0041(9) 0.0101(10) -0.0032(10) C15 0.0841(18) 0.0575(16) 0.0265(12) -0.0044(12) 0.0032(11) 0.0202(14) C16 0.157(3) 0.0344(14) 0.0238(13) -0.0005(11) 0.0036(16) 0.0117(16) C17 0.160(3) 0.0343(14) 0.0238(13) -0.0031(11) 0.0140(16) -0.0319(16) C18 0.0895(18) 0.0399(13) 0.0258(11) -0.0050(10) 0.0124(11) -0.0260(12) C19 0.0299(10) 0.0290(10) 0.0237(10) 0.0013(8) 0.0070(8) -0.0035(8) B1 0.0283(11) 0.0329(12) 0.0270(12) -0.0023(10) 0.0073(9) -0.0087(9) B2 0.0311(11) 0.0316(12) 0.0223(11) 0.0007(10) 0.0099(9) 0.0016(9) B3 0.0323(11) 0.0370(13) 0.0268(12) -0.0047(10) 0.0081(9) -0.0020(10) B4 0.0442(13) 0.0312(13) 0.0363(13) -0.0043(11) 0.0127(11) -0.0044(10) B5 0.0381(12) 0.0291(12) 0.0337(13) 0.0025(10) 0.0113(10) -0.0024(10) B6 0.0333(12) 0.0336(12) 0.0246(12) -0.0037(10) 0.0068(9) -0.0021(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 N1 C7B 1.337(2) . ? N1 C1 1.406(2) . ? N1 B1 1.435(3) . ? N1 C7A 1.487(2) . ? N1 C7C 1.588(2) . ? N2 C2 1.410(2) . ? N2 C13 1.439(2) . ? N2 B1 1.441(3) . ? C1 C6 1.380(3) . ? C1 C2 1.386(3) . ? C2 C3 1.391(3) . ? C3 C4 1.384(3) . ? C3 H3A 0.9500 . ? C4 C5 1.377(4) . ? C4 H4A 0.9500 . ? C5 C6 1.388(3) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7A C8A 1.3900 . ? C7A C12A 1.3900 . ? C8A C9A 1.3900 . ? C8A H8A 0.9500 . ? C9A C10A 1.3900 . ? C9A H9A 0.9500 . ? C10A C11A 1.3900 . ? C10A H10A 0.9500 . ? C11A C12A 1.3900 . ? C11A H11A 0.9500 . ? C12A H12A 0.9500 . ? C7B C8B 1.3896 . ? C7B C12B 1.3899 . ? C8B C9B 1.3897 . ? C8B H8B 0.9500 . ? C9B C10B 1.3898 . ? C9B H9B 0.9500 . ? C10B C11B 1.3896 . ? C10B H10B 0.9500 . ? C11B C12B 1.3897 . ? C11B H11B 0.9500 . ? C12B H12B 0.9500 . ? C7C C8C 1.3895 . ? C7C C12C 1.3899 . ? C8C C9C 1.3898 . ? C8C H8C 0.9500 . ? C9C C10C 1.3897 . ? C9C H9C 0.9500 . ? C10C C11C 1.3895 . ? C10C H10C 0.9500 . ? C11C C12C 1.3898 . ? C11C H11C 0.9500 . ? C12C H12C 0.9500 . ? C13 C14 1.378(3) . ? C13 C18 1.388(3) . ? C14 C15 1.387(3) . ? C14 H14A 0.9500 . ? C15 C16 1.377(4) . ? C15 H15A 0.9500 . ? C16 C17 1.365(4) . ? C16 H16A 0.9500 . ? C17 C18 1.386(4) . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? C19 B1 1.587(3) . ? C19 B2 1.704(3) 2 ? C19 B6 1.725(3) . ? C19 B3 1.729(3) 2 ? C19 B5 1.729(3) . ? C19 B2 1.737(3) . ? B2 C19 1.704(3) 2 ? B2 B3 1.757(3) . ? B2 B6 1.769(3) . ? B2 B2 1.784(4) 2 ? B2 H2 1.061(18) . ? B3 C19 1.729(3) 2 ? B3 B6 1.764(3) . ? B3 B5 1.771(3) 2 ? B3 B4 1.775(3) . ? B3 H3 1.098(18) . ? B4 B5 1.771(3) . ? B4 B5 1.772(3) 2 ? B4 B6 1.780(3) . ? B4 B4 1.791(5) 2 ? B4 H4 1.11(2) . ? B5 B3 1.771(3) 2 ? B5 B4 1.772(3) 2 ? B5 B6 1.779(3) . ? B5 H5 1.096(19) . ? B6 H6 1.111(18) . ? 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 C7B N1 C1 118.64(16) . . ? C7B N1 B1 132.79(15) . . ? C1 N1 B1 108.36(16) . . ? C7B N1 C7A 11.1 . . ? C1 N1 C7A 118.38(15) . . ? B1 N1 C7A 132.62(14) . . ? C7B N1 C7C 18.5 . . ? C1 N1 C7C 117.91(15) . . ? B1 N1 C7C 131.08(14) . . ? C7A N1 C7C 7.4 . . ? C2 N2 C13 117.87(15) . . ? C2 N2 B1 107.70(16) . . ? C13 N2 B1 134.43(16) . . ? C6 C1 C2 121.27(18) . . ? C6 C1 N1 130.1(2) . . ? C2 C1 N1 108.66(17) . . ? C1 C2 C3 121.10(19) . . ? C1 C2 N2 109.14(16) . . ? C3 C2 N2 129.7(2) . . ? C4 C3 C2 117.2(2) . . ? C4 C3 H3A 121.4 . . ? C2 C3 H3A 121.4 . . ? C5 C4 C3 121.6(2) . . ? C5 C4 H4A 119.2 . . ? C3 C4 H4A 119.2 . . ? C4 C5 C6 121.2(2) . . ? C4 C5 H5A 119.4 . . ? C6 C5 H5A 119.4 . . ? C1 C6 C5 117.6(2) . . ? C1 C6 H6A 121.2 . . ? C5 C6 H6A 121.2 . . ? C8A C7A C12A 120.0 . . ? C8A C7A N1 119.27(12) . . ? C12A C7A N1 120.70(12) . . ? C7A C8A C9A 120.0 . . ? C7A C8A H8A 120.0 . . ? C9A C8A H8A 120.0 . . ? C10A C9A C8A 120.0 . . ? C10A C9A H9A 120.0 . . ? C8A C9A H9A 120.0 . . ? C11A C10A C9A 120.0 . . ? C11A C10A H10A 120.0 . . ? C9A C10A H10A 120.0 . . ? C12A C11A C10A 120.0 . . ? C12A C11A H11A 120.0 . . ? C10A C11A H11A 120.0 . . ? C11A C12A C7A 120.0 . . ? C11A C12A H12A 120.0 . . ? C7A C12A H12A 120.0 . . ? N1 C7B C8B 124.02(14) . . ? N1 C7B C12B 115.82(14) . . ? C8B C7B C12B 120.0 . . ? C7B C8B C9B 120.0 . . ? C7B C8B H8B 120.0 . . ? C9B C8B H8B 120.0 . . ? C8B C9B C10B 120.0 . . ? C8B C9B H9B 120.0 . . ? C10B C9B H9B 120.0 . . ? C11B C10B C9B 120.0 . . ? C11B C10B H10B 120.0 . . ? C9B C10B H10B 120.0 . . ? C10B C11B C12B 120.0 . . ? C10B C11B H11B 120.0 . . ? C12B C11B H11B 120.0 . . ? C11B C12B C7B 120.0 . . ? C11B C12B H12B 120.0 . . ? C7B C12B H12B 120.0 . . ? C8C C7C C12C 120.0 . . ? C8C C7C N1 117.92(11) . . ? C12C C7C N1 122.10(11) . . ? C7C C8C C9C 120.0 . . ? C7C C8C H8C 120.0 . . ? C9C C8C H8C 120.0 . . ? C10C C9C C8C 120.0 . . ? C10C C9C H9C 120.0 . . ? C8C C9C H9C 120.0 . . ? C11C C10C C9C 120.0 . . ? C11C C10C H10C 120.0 . . ? C9C C10C H10C 120.0 . . ? C10C C11C C12C 120.0 . . ? C10C C11C H11C 120.0 . . ? C12C C11C H11C 120.0 . . ? C11C C12C C7C 120.0 . . ? C11C C12C H12C 120.0 . . ? C7C C12C H12C 120.0 . . ? C14 C13 C18 120.1(2) . . ? C14 C13 N2 120.41(17) . . ? C18 C13 N2 119.35(19) . . ? C13 C14 C15 119.6(2) . . ? C13 C14 H14A 120.2 . . ? C15 C14 H14A 120.2 . . ? C16 C15 C14 120.4(3) . . ? C16 C15 H15A 119.8 . . ? C14 C15 H15A 119.8 . . ? C17 C16 C15 119.9(2) . . ? C17 C16 H16A 120.1 . . ? C15 C16 H16A 120.1 . . ? C16 C17 C18 120.7(2) . . ? C16 C17 H17A 119.6 . . ? C18 C17 H17A 119.6 . . ? C17 C18 C13 119.3(2) . . ? C17 C18 H18A 120.3 . . ? C13 C18 H18A 120.3 . . ? B1 C19 B2 123.62(15) . 2 ? B1 C19 B6 114.58(14) . . ? B2 C19 B6 113.01(14) 2 . ? B1 C19 B3 121.16(15) . 2 ? B2 C19 B3 61.56(12) 2 2 ? B6 C19 B3 112.56(15) . 2 ? B1 C19 B5 115.69(15) . . ? B2 C19 B5 112.25(14) 2 . ? B6 C19 B5 62.00(12) . . ? B3 C19 B5 61.60(12) 2 . ? B1 C19 B2 120.13(15) . . ? B2 C19 B2 62.44(14) 2 . ? B6 C19 B2 61.44(12) . . ? B3 C19 B2 112.28(14) 2 . ? B5 C19 B2 111.93(14) . . ? N1 B1 N2 106.10(16) . . ? N1 B1 C19 125.66(17) . . ? N2 B1 C19 127.64(18) . . ? C19 B2 C19 103.21(15) 2 . ? C19 B2 B3 59.91(12) 2 . ? C19 B2 B3 105.67(15) . . ? C19 B2 B6 106.31(15) 2 . ? C19 B2 B6 58.93(11) . . ? B3 B2 B6 60.04(12) . . ? C19 B2 B2 59.68(12) 2 2 ? C19 B2 B2 57.87(12) . 2 ? B3 B2 B2 108.74(12) . 2 ? B6 B2 B2 107.20(13) . 2 ? C19 B2 H2 121.5(9) 2 . ? C19 B2 H2 124.2(10) . . ? B3 B2 H2 124.3(10) . . ? B6 B2 H2 126.0(9) . . ? B2 B2 H2 117.4(9) 2 . ? C19 B3 B2 58.54(11) 2 . ? C19 B3 B6 105.46(15) 2 . ? B2 B3 B6 60.31(12) . . ? C19 B3 B5 59.21(12) 2 2 ? B2 B3 B5 107.83(15) . 2 ? B6 B3 B5 107.96(16) . 2 ? C19 B3 B4 106.05(15) 2 . ? B2 B3 B4 108.78(16) . . ? B6 B3 B4 60.40(13) . . ? B5 B3 B4 59.98(13) 2 . ? C19 B3 H3 120.5(10) 2 . ? B2 B3 H3 117.7(10) . . ? B6 B3 H3 123.1(9) . . ? B5 B3 H3 123.1(10) 2 . ? B4 B3 H3 126.1(10) . . ? B5 B4 B5 107.02(17) . 2 ? B5 B4 B3 107.47(16) . . ? B5 B4 B3 59.89(13) 2 . ? B5 B4 B6 60.11(13) . . ? B5 B4 B6 107.17(16) 2 . ? B3 B4 B6 59.49(12) . . ? B5 B4 B4 59.66(14) . 2 ? B5 B4 B4 59.62(14) 2 2 ? B3 B4 B4 107.69(13) . 2 ? B6 B4 B4 107.73(14) . 2 ? B5 B4 H4 121.3(10) . . ? B5 B4 H4 123.7(10) 2 . ? B3 B4 H4 121.8(10) . . ? B6 B4 H4 120.5(10) . . ? B4 B4 H4 122.9(10) 2 . ? C19 B5 B3 59.19(12) . 2 ? C19 B5 B4 106.11(15) . . ? B3 B5 B4 108.75(16) 2 . ? C19 B5 B4 106.16(15) . 2 ? B3 B5 B4 60.13(13) 2 2 ? B4 B5 B4 60.72(16) . 2 ? C19 B5 B6 58.87(11) . . ? B3 B5 B6 108.04(15) 2 . ? B4 B5 B6 60.19(13) . . ? B4 B5 B6 108.63(16) 2 . ? C19 B5 H5 117.9(10) . . ? B3 B5 H5 120.0(10) 2 . ? B4 B5 H5 125.8(10) . . ? B4 B5 H5 126.7(10) 2 . ? B6 B5 H5 118.9(10) . . ? C19 B6 B3 105.92(14) . . ? C19 B6 B2 59.63(11) . . ? B3 B6 B2 59.65(12) . . ? C19 B6 B5 59.13(12) . . ? B3 B6 B5 107.63(15) . . ? B2 B6 B5 108.15(15) . . ? C19 B6 B4 105.93(15) . . ? B3 B6 B4 60.10(13) . . ? B2 B6 B4 108.02(15) . . ? B5 B6 B4 59.70(13) . . ? C19 B6 H6 119.1(9) . . ? B3 B6 H6 124.9(9) . . ? B2 B6 H6 118.7(9) . . ? B5 B6 H6 121.6(9) . . ? B4 B6 H6 126.5(9) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.209 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.038 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound21 _database_code_depnum_ccdc_archive 'CCDC 929985' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '3(C38 H38 B12 N4), 4(C H2 Cl2)' _chemical_formula_sum 'C118 H122 B36 Cl8 N12' _chemical_formula_weight 2381.04 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.3487(16) _cell_length_b 24.8869(12) _cell_length_c 22.5365(11) _cell_angle_alpha 90.00 _cell_angle_beta 130.554(3) _cell_angle_gamma 90.00 _cell_volume 12506.7(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9475 _cell_measurement_theta_min 2.314 _cell_measurement_theta_max 26.954 _exptl_crystal_description octahedron _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4920 _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9222 _exptl_absorpt_correction_T_max 0.9568 _exptl_absorpt_process_details 'SADABS 2008/1 (Bruker AXS, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_measurement_device 'Bruker KAPPA APEX II ' _diffrn_radiation_source 'fine focus sealed tube ' _diffrn_radiation_monochromator 'graphite monochromator ' _diffrn_measurement_device_type 'four three circle diffractometer' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 180817 _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_sigmaI/netI 0.0169 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 27.50 _reflns_number_total 14347 _reflns_number_gt 12351 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2009.11-0 (Bruker AXS, 2009)' _computing_cell_refinement 'APEX2 v2009.11-0 (Bruker AXS, 2009)' _computing_data_reduction 'SAINT (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND 2.1 (Crystal Impact, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Disorder of CH2Cl2 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^)+(0.1288P)^2^+20.3583P] 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 14347 _refine_ls_number_parameters 817 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0837 _refine_ls_R_factor_gt 0.0703 _refine_ls_wR_factor_ref 0.2173 _refine_ls_wR_factor_gt 0.1976 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.003 _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 N1 N 0.69136(12) 0.46609(10) 0.57758(15) 0.0264(5) Uani 1 1 d . . . N2 N 0.78900(12) 0.49435(10) 0.65781(15) 0.0278(5) Uani 1 1 d . . . N3 N 0.61761(13) 0.76173(10) 0.65672(15) 0.0277(5) Uani 1 1 d . . . N4 N 0.63508(12) 0.78836(9) 0.57591(15) 0.0248(5) Uani 1 1 d . . . B1 B 0.72908(16) 0.51124(13) 0.6223(2) 0.0256(7) Uani 1 1 d . . . B2 B 0.64256(16) 0.74417(13) 0.62254(19) 0.0250(6) Uani 1 1 d . . . B3 B 0.65650(17) 0.57629(14) 0.6372(2) 0.0297(7) Uani 1 1 d . . . H3 H 0.6352 0.5419 0.6434 0.036 Uiso 1 1 calc R . . B4 B 0.63924(16) 0.59030(13) 0.5471(2) 0.0277(7) Uani 1 1 d . . . H4 H 0.6068 0.5652 0.4937 0.033 Uiso 1 1 calc R . . B5 B 0.70362(18) 0.61817(14) 0.5686(2) 0.0297(7) Uani 1 1 d . . . H5 H 0.7141 0.6114 0.5294 0.036 Uiso 1 1 calc R . . B6 B 0.76046(16) 0.62119(14) 0.6706(2) 0.0320(8) Uani 1 1 d . . . H6 H 0.8088 0.6164 0.6992 0.038 Uiso 1 1 calc R . . B7 B 0.73181(19) 0.59462(15) 0.7135(2) 0.0342(8) Uani 1 1 d . . . H7 H 0.7609 0.5721 0.7701 0.041 Uiso 1 1 calc R . . B8 B 0.67375(19) 0.63738(15) 0.6878(2) 0.0325(8) Uani 1 1 d . . . H8 H 0.6640 0.6442 0.7277 0.039 Uiso 1 1 calc R . . B9 B 0.61639(16) 0.63473(13) 0.5849(2) 0.0288(7) Uani 1 1 d . . . H9 H 0.5680 0.6399 0.5560 0.035 Uiso 1 1 calc R . . B10 B 0.64576(17) 0.66030(12) 0.5427(2) 0.0265(7) Uani 1 1 d . . . H10 H 0.6171 0.6826 0.4859 0.032 Uiso 1 1 calc R . . B11 B 0.72020(17) 0.67898(14) 0.6187(2) 0.0300(7) Uani 1 1 d . . . H11 H 0.7414 0.7136 0.6128 0.036 Uiso 1 1 calc R . . B12 B 0.73733(18) 0.66534(15) 0.7082(2) 0.0349(8) Uani 1 1 d . . . H12 H 0.7695 0.6908 0.7613 0.042 Uiso 1 1 calc R . . C1 C 0.72667(16) 0.42458(12) 0.58451(18) 0.0303(7) Uani 1 1 d . . . C2 C 0.78581(15) 0.44207(12) 0.63316(18) 0.0286(6) Uani 1 1 d . . . C3 C 0.83154(17) 0.40877(14) 0.6511(2) 0.0370(8) Uani 1 1 d . . . H3A H 0.8721 0.4203 0.6851 0.044 Uiso 1 1 calc R . . C4 C 0.81525(19) 0.35794(16) 0.6173(2) 0.0422(8) Uani 1 1 d . . . H4A H 0.8453 0.3344 0.6280 0.051 Uiso 1 1 calc R . . C5 C 0.7557(2) 0.34081(15) 0.5678(2) 0.0433(9) Uani 1 1 d . . . H5A H 0.7460 0.3060 0.5452 0.052 Uiso 1 1 calc R . . C6 C 0.71015(19) 0.37375(12) 0.5510(2) 0.0354(7) Uani 1 1 d . . . H6A H 0.6696 0.3620 0.5180 0.043 Uiso 1 1 calc R . . C7 C 0.62842(15) 0.45672(11) 0.52930(19) 0.0285(6) Uani 1 1 d . . . C8 C 0.60256(17) 0.44504(13) 0.5620(2) 0.0339(7) Uani 1 1 d . . . H8A H 0.6264 0.4443 0.6171 0.041 Uiso 1 1 calc R . . C9 C 0.54259(18) 0.43459(15) 0.5143(2) 0.0443(9) Uani 1 1 d . . . H9A H 0.5243 0.4281 0.5362 0.053 Uiso 1 1 calc R . . C10 C 0.50798(17) 0.43334(15) 0.4335(2) 0.0435(9) Uani 1 1 d . . . H10A H 0.4665 0.4248 0.4007 0.052 Uiso 1 1 calc R . . C11 C 0.53324(17) 0.44432(14) 0.4012(2) 0.0389(8) Uani 1 1 d . . . H11A H 0.5093 0.4437 0.3460 0.047 Uiso 1 1 calc R . . C12 C 0.59385(16) 0.45647(12) 0.4486(2) 0.0317(7) Uani 1 1 d . . . H12A H 0.6115 0.4645 0.4262 0.038 Uiso 1 1 calc R . . C13 C 0.84569(14) 0.52042(13) 0.7078(2) 0.0320(7) Uani 1 1 d . . . C14 C 0.8686(2) 0.54364(18) 0.6762(3) 0.0484(10) Uani 1 1 d . . . H14 H 0.8462 0.5425 0.6214 0.058 Uiso 1 1 calc R . . C15 C 0.9242(2) 0.5685(2) 0.7245(3) 0.0593(12) Uani 1 1 d . . . H15 H 0.9394 0.5853 0.7028 0.071 Uiso 1 1 calc R . . C16 C 0.95759(18) 0.56869(18) 0.8049(3) 0.0572(12) Uani 1 1 d . . . H16 H 0.9964 0.5843 0.8384 0.069 Uiso 1 1 calc R . . C17 C 0.93358(19) 0.54565(15) 0.8363(3) 0.0526(12) Uani 1 1 d . . . H17 H 0.9556 0.5466 0.8910 0.063 Uiso 1 1 calc R . . C18 C 0.87824(17) 0.52179(14) 0.7876(2) 0.0402(8) Uani 1 1 d . . . H18 H 0.8621 0.5061 0.8088 0.048 Uiso 1 1 calc R . . C19 C 0.59695(15) 0.81438(12) 0.63270(19) 0.0296(6) Uani 1 1 d . . . C20 C 0.60747(15) 0.83089(12) 0.58314(18) 0.0266(6) Uani 1 1 d . . . C21 C 0.59107(16) 0.88133(13) 0.54992(19) 0.0321(7) Uani 1 1 d . . . H21 H 0.5981 0.8924 0.5162 0.039 Uiso 1 1 calc R . . C22 C 0.56389(17) 0.91527(13) 0.5676(2) 0.0362(8) Uani 1 1 d . . . H22 H 0.5518 0.9502 0.5452 0.043 Uiso 1 1 calc R . . C23 C 0.55416(17) 0.89930(15) 0.6169(2) 0.0402(8) Uani 1 1 d . . . H23 H 0.5362 0.9238 0.6287 0.048 Uiso 1 1 calc R . . C24 C 0.56983(16) 0.84848(14) 0.6499(2) 0.0350(7) Uani 1 1 d . . . H24 H 0.5622 0.8375 0.6831 0.042 Uiso 1 1 calc R . . C25 C 0.61028(18) 0.73570(13) 0.7074(2) 0.0342(7) Uani 1 1 d . . . C26 C 0.6553(2) 0.73740(15) 0.7864(2) 0.0461(9) Uani 1 1 d . . . H26 H 0.6923 0.7545 0.8087 0.055 Uiso 1 1 calc R . . C27 C 0.6461(3) 0.71325(17) 0.8346(3) 0.0537(11) Uani 1 1 d . . . H27 H 0.6767 0.7147 0.8898 0.064 Uiso 1 1 calc R . . C28 C 0.5942(3) 0.68825(19) 0.8027(3) 0.0599(13) Uani 1 1 d . . . H28 H 0.5886 0.6720 0.8358 0.072 Uiso 1 1 calc R . . C29 C 0.5490(2) 0.6858(2) 0.7234(3) 0.0593(12) Uani 1 1 d . . . H29 H 0.5126 0.6676 0.7015 0.071 Uiso 1 1 calc R . . C30 C 0.55699(19) 0.70997(17) 0.6753(3) 0.0440(9) Uani 1 1 d . . . H30 H 0.5258 0.7089 0.6202 0.053 Uiso 1 1 calc R . . C31 C 0.64947(14) 0.79699(11) 0.52633(18) 0.0244(6) Uani 1 1 d . . . C32 C 0.60488(16) 0.79319(12) 0.44644(19) 0.0292(6) Uani 1 1 d . . . H32 H 0.5653 0.7833 0.4242 0.035 Uiso 1 1 calc R . . C33 C 0.61820(18) 0.80391(14) 0.3986(2) 0.0380(8) Uani 1 1 d . . . H33 H 0.5875 0.8014 0.3435 0.046 Uiso 1 1 calc R . . C34 C 0.6753(2) 0.81815(15) 0.4303(2) 0.0409(8) Uani 1 1 d . . . H34 H 0.6843 0.8249 0.3974 0.049 Uiso 1 1 calc R . . C35 C 0.71987(18) 0.82261(15) 0.5107(2) 0.0387(8) Uani 1 1 d . . . H35 H 0.7595 0.8323 0.5330 0.046 Uiso 1 1 calc R . . C36 C 0.70652(16) 0.81286(13) 0.5591(2) 0.0325(7) Uani 1 1 d . . . H36 H 0.7365 0.8171 0.6140 0.039 Uiso 1 1 calc R . . C37 C 0.70908(13) 0.56907(11) 0.62681(16) 0.0221(5) Uani 1 1 d . . . C38 C 0.66703(14) 0.68592(11) 0.62827(17) 0.0232(6) Uani 1 1 d . . . N5A N 0.37754(10) 0.66458(9) 0.28104(14) 0.0206(5) Uani 1 1 d . . . N6A N 0.34680(11) 0.58457(10) 0.21607(14) 0.0216(5) Uani 1 1 d . . . B13A B 0.39173(14) 0.62540(14) 0.2488(2) 0.0210(5) Uani 1 1 d . . . B14A B 0.48798(15) 0.68477(13) 0.2769(2) 0.0262(6) Uani 1 1 d . . . H14A H 0.4797 0.7230 0.2948 0.031 Uiso 1 1 calc R . . B15A B 0.43925(15) 0.66273(15) 0.1785(2) 0.0289(6) Uani 1 1 d . . . H15A H 0.3983 0.6862 0.1313 0.035 Uiso 1 1 calc R . . B16A B 0.43953(16) 0.59174(15) 0.1778(2) 0.0317(7) Uani 1 1 d . . . H16A H 0.3989 0.5684 0.1296 0.038 Uiso 1 1 calc R . . B17A B 0.48761(17) 0.56971(13) 0.2768(2) 0.0325(7) Uani 1 1 d . . . H17A H 0.4791 0.5316 0.2945 0.039 Uiso 1 1 calc R . . B18A B 0.51642(15) 0.62756(15) 0.33667(19) 0.0289(7) Uani 1 1 d . . . H18A H 0.5266 0.6281 0.3939 0.035 Uiso 1 1 calc R . . C39A C 0.32624(13) 0.64833(11) 0.26848(17) 0.0216(5) Uani 1 1 d . . . C40A C 0.30767(13) 0.59932(11) 0.22915(17) 0.0217(5) Uani 1 1 d . . . C41A C 0.25786(13) 0.57272(12) 0.20960(17) 0.0246(6) Uani 1 1 d . . . H41A H 0.2452 0.5391 0.1833 0.030 Uiso 1 1 calc R . . C42A C 0.22725(14) 0.59731(13) 0.23021(18) 0.0277(6) Uani 1 1 d . . . H42A H 0.1932 0.5800 0.2181 0.033 Uiso 1 1 calc R . . C43A C 0.24530(15) 0.64630(13) 0.2679(2) 0.0302(6) Uani 1 1 d . . . H43A H 0.2231 0.6623 0.2804 0.036 Uiso 1 1 calc R . . C44A C 0.29515(14) 0.67250(12) 0.28779(17) 0.0256(6) Uani 1 1 d . . . H44A H 0.3076 0.7061 0.3140 0.031 Uiso 1 1 calc R . . C45A C 0.40595(12) 0.71314(11) 0.32477(17) 0.0217(5) Uani 1 1 d . . . C46A C 0.38504(15) 0.76211(13) 0.2878(2) 0.0356(7) Uani 1 1 d . . . H46A H 0.3533 0.7637 0.2329 0.043 Uiso 1 1 calc R . . C47A C 0.41018(17) 0.80886(14) 0.3304(3) 0.0526(12) Uani 1 1 d . . . H47A H 0.3957 0.8427 0.3049 0.063 Uiso 1 1 calc R . . C48A C 0.45642(17) 0.80658(15) 0.4102(3) 0.0476(10) Uani 1 1 d . . . H48A H 0.4742 0.8388 0.4395 0.057 Uiso 1 1 calc R . . C49A C 0.47660(17) 0.75753(15) 0.4471(2) 0.0368(7) Uani 1 1 d . . . H49A H 0.5083 0.7560 0.5020 0.044 Uiso 1 1 calc R . . C50A C 0.45108(14) 0.71018(13) 0.40462(19) 0.0286(6) Uani 1 1 d . . . H50A H 0.4645 0.6763 0.4303 0.034 Uiso 1 1 calc R . . C51A C 0.33519(14) 0.53480(12) 0.17741(18) 0.0251(6) Uani 1 1 d . . . C52A C 0.36386(19) 0.48893(12) 0.2218(2) 0.0364(8) Uani 1 1 d . . . H52A H 0.3936 0.4908 0.2771 0.044 Uiso 1 1 calc R . . C53A C 0.3476(2) 0.44009(14) 0.1827(3) 0.0522(12) Uani 1 1 d . . . H53A H 0.3658 0.4080 0.2121 0.063 Uiso 1 1 calc R . . C54A C 0.3063(2) 0.43707(17) 0.1034(3) 0.0568(13) Uani 1 1 d . . . H54A H 0.2969 0.4033 0.0780 0.068 Uiso 1 1 calc R . . C55A C 0.2785(2) 0.48246(19) 0.0607(3) 0.0528(12) Uani 1 1 d . . . H55A H 0.2491 0.4801 0.0054 0.063 Uiso 1 1 calc R . . C56A C 0.29256(16) 0.53228(15) 0.0969(2) 0.0359(7) Uani 1 1 d . . . H56A H 0.2732 0.5640 0.0668 0.043 Uiso 1 1 calc R . . C57A C 0.44593(12) 0.62649(12) 0.24900(19) 0.0201(4) Uani 1 1 d . . . Cl1 Cl 0.70265(15) 0.18626(17) 0.5621(2) 0.0937(10) Uani 0.50 1 d PD A . Cl2A Cl 0.5862(3) 0.2282(4) 0.4470(8) 0.0746(19) Uani 0.25 1 d PD A 1 Cl2B Cl 0.5976(4) 0.2457(4) 0.4534(8) 0.0746(19) Uani 0.25 1 d PD A 2 C58 C 0.6481(4) 0.2230(4) 0.5461(4) 0.054(2) Uani 0.50 1 d P . . H58A H 0.6635 0.2594 0.5680 0.065 Uiso 0.25 1 calc PR A 1 H58B H 0.6355 0.2064 0.5734 0.065 Uiso 0.25 1 calc PR A 1 H58C H 0.6662 0.2541 0.5821 0.065 Uiso 0.25 1 calc PR A 2 H58D H 0.6269 0.2010 0.5582 0.065 Uiso 0.25 1 calc PR A 2 Cl3 Cl 0.89456(18) 0.50632(11) 1.04897(19) 0.1175(10) Uani 0.849(4) 1 d PD B 1 Cl4 Cl 0.88942(16) 0.57953(14) 0.9463(2) 0.1246(10) Uani 0.849(4) 1 d PD B 1 C59 C 0.8615(7) 0.5548(8) 0.9839(12) 0.253(13) Uani 0.849(4) 1 d PD B 1 H59C H 0.8206 0.5419 0.9397 0.304 Uiso 0.849(4) 1 calc PR B 1 H59D H 0.8567 0.5852 1.0077 0.304 Uiso 0.849(4) 1 calc PR B 1 Cl3B Cl 0.8607(9) 0.4854(6) 1.0010(11) 0.1175(10) Uani 0.151(4) 1 d PD B 2 Cl4B Cl 0.9130(9) 0.5739(8) 0.9904(11) 0.1246(10) Uani 0.151(4) 1 d PD B 2 C59B C 0.863(3) 0.527(2) 0.947(2) 0.253(13) Uani 0.151(4) 1 d PD B 2 H59A H 0.8229 0.5442 0.9109 0.304 Uiso 0.151(4) 1 calc PR B 2 H59B H 0.8684 0.5055 0.9156 0.304 Uiso 0.151(4) 1 calc PR B 2 Cl5 Cl 0.5000 0.18088(10) 0.2500 0.1401(16) Uani 1 2 d S . . Cl6 Cl 0.5000 0.06661(9) 0.2500 0.0946(8) Uani 1 2 d S . . C60 C 0.5351(5) 0.1228(5) 0.3185(6) 0.067(2) Uani 0.50 1 d P . . H60A H 0.5792 0.1226 0.3507 0.081 Uiso 0.50 1 calc PR . . H60B H 0.5253 0.1226 0.3530 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 N1 0.0280(13) 0.0221(11) 0.0217(12) 0.0040(9) 0.0129(11) 0.0023(10) N2 0.0245(13) 0.0264(12) 0.0269(13) 0.0025(10) 0.0143(11) 0.0013(10) N3 0.0348(14) 0.0257(12) 0.0265(13) -0.0035(10) 0.0218(12) -0.0047(10) N4 0.0312(13) 0.0221(11) 0.0245(12) -0.0007(9) 0.0196(11) -0.0025(10) B1 0.0260(16) 0.0238(15) 0.0243(16) 0.0024(12) 0.0150(14) -0.0001(12) B2 0.0286(16) 0.0243(14) 0.0210(15) -0.0048(11) 0.0157(14) -0.0060(12) B3 0.0339(17) 0.0250(15) 0.044(2) 0.0060(13) 0.0315(17) -0.0010(13) B4 0.0239(15) 0.0225(15) 0.0250(16) 0.0011(12) 0.0108(14) -0.0024(12) B5 0.045(2) 0.0216(14) 0.0391(19) 0.0013(13) 0.0346(18) -0.0042(13) B6 0.0222(16) 0.0240(15) 0.043(2) -0.0062(13) 0.0178(15) -0.0059(12) B7 0.041(2) 0.0305(17) 0.0210(16) 0.0032(13) 0.0156(15) 0.0045(15) B8 0.047(2) 0.0301(16) 0.0314(17) 0.0075(14) 0.0305(17) 0.0056(15) B9 0.0271(16) 0.0199(14) 0.0400(19) 0.0005(13) 0.0221(15) -0.0026(12) B10 0.0401(18) 0.0170(13) 0.0217(15) -0.0020(11) 0.0199(15) -0.0042(12) B11 0.0298(17) 0.0226(15) 0.046(2) -0.0044(13) 0.0283(17) -0.0065(12) B12 0.0305(18) 0.0312(17) 0.0252(17) -0.0043(13) 0.0103(15) -0.0006(14) C1 0.0372(18) 0.0256(14) 0.0218(14) 0.0069(11) 0.0164(14) 0.0054(13) C2 0.0297(16) 0.0267(14) 0.0242(15) 0.0064(11) 0.0153(13) 0.0080(12) C3 0.0355(18) 0.0376(18) 0.0326(17) 0.0075(13) 0.0198(16) 0.0110(14) C4 0.048(2) 0.0359(17) 0.0393(19) 0.0077(15) 0.0269(18) 0.0150(16) C5 0.060(3) 0.0308(17) 0.0336(18) 0.0032(14) 0.0284(19) 0.0122(16) C6 0.046(2) 0.0262(16) 0.0263(16) 0.0033(12) 0.0202(16) 0.0035(14) C7 0.0294(16) 0.0149(12) 0.0272(15) 0.0027(10) 0.0123(14) -0.0021(11) C8 0.0374(18) 0.0263(14) 0.0316(17) 0.0039(12) 0.0196(15) -0.0040(13) C9 0.041(2) 0.0380(18) 0.052(2) 0.0082(16) 0.0293(19) -0.0094(15) C10 0.0321(18) 0.0386(18) 0.041(2) 0.0067(15) 0.0157(17) -0.0120(15) C11 0.0316(17) 0.0312(16) 0.0332(18) 0.0054(13) 0.0119(15) -0.0085(13) C12 0.0301(16) 0.0235(13) 0.0289(16) 0.0024(12) 0.0136(14) -0.0052(12) C13 0.0220(15) 0.0280(14) 0.0367(17) 0.0036(12) 0.0149(14) 0.0037(11) C14 0.042(2) 0.058(2) 0.056(2) -0.0051(19) 0.036(2) -0.0033(18) C15 0.050(3) 0.063(3) 0.085(4) -0.010(2) 0.053(3) -0.010(2) C16 0.0267(18) 0.046(2) 0.078(3) -0.014(2) 0.025(2) -0.0059(16) C17 0.0338(19) 0.0309(17) 0.045(2) 0.0026(15) 0.0039(17) 0.0031(14) C18 0.0340(18) 0.0298(16) 0.0360(18) 0.0084(13) 0.0135(16) 0.0000(13) C19 0.0300(16) 0.0263(14) 0.0245(14) -0.0048(11) 0.0142(13) -0.0040(12) C20 0.0306(15) 0.0244(13) 0.0219(14) -0.0043(11) 0.0158(13) -0.0020(11) C21 0.0350(17) 0.0277(14) 0.0224(15) -0.0045(11) 0.0137(14) -0.0024(12) C22 0.0369(18) 0.0245(14) 0.0310(17) -0.0036(12) 0.0149(15) 0.0008(12) C23 0.0372(19) 0.0351(17) 0.0389(19) -0.0101(14) 0.0205(16) 0.0012(14) C24 0.0365(18) 0.0369(17) 0.0293(16) -0.0064(13) 0.0204(15) 0.0004(14) C25 0.050(2) 0.0309(15) 0.0396(18) -0.0010(13) 0.0369(18) 0.0001(14) C26 0.073(3) 0.0345(17) 0.0360(18) -0.0077(14) 0.038(2) -0.0135(17) C27 0.088(3) 0.044(2) 0.043(2) -0.0053(17) 0.048(2) -0.008(2) C28 0.096(4) 0.051(2) 0.081(4) 0.002(2) 0.080(3) -0.002(2) C29 0.069(3) 0.064(3) 0.082(4) 0.010(2) 0.066(3) 0.003(2) C30 0.043(2) 0.051(2) 0.052(2) 0.0062(18) 0.037(2) 0.0012(17) C31 0.0311(15) 0.0195(12) 0.0256(14) 0.0000(10) 0.0198(13) -0.0033(11) C32 0.0339(16) 0.0247(13) 0.0259(15) -0.0013(11) 0.0181(14) -0.0049(12) C33 0.050(2) 0.0341(17) 0.0267(16) 0.0006(13) 0.0233(16) -0.0073(15) C34 0.061(2) 0.0362(17) 0.046(2) 0.0007(15) 0.044(2) -0.0085(16) C35 0.0414(19) 0.0388(18) 0.0396(19) 0.0047(14) 0.0279(17) -0.0085(15) C36 0.0318(17) 0.0321(16) 0.0294(16) 0.0004(12) 0.0181(14) -0.0067(12) C37 0.0209(13) 0.0226(12) 0.0201(13) 0.0010(10) 0.0123(12) -0.0012(10) C38 0.0265(14) 0.0218(12) 0.0253(14) -0.0032(10) 0.0186(13) -0.0070(10) N5A 0.0180(11) 0.0222(11) 0.0213(11) -0.0012(9) 0.0126(10) -0.0008(9) N6A 0.0194(11) 0.0227(11) 0.0223(11) -0.0021(9) 0.0133(10) -0.0029(9) B13A 0.0208(15) 0.0220(11) 0.0200(11) -0.0003(9) 0.0132(13) -0.0004(12) B14A 0.0306(16) 0.0240(14) 0.0327(16) -0.0033(12) 0.0244(15) -0.0039(12) B15A 0.0270(15) 0.0355(17) 0.0312(16) 0.0064(14) 0.0221(14) 0.0052(13) B16A 0.0308(17) 0.0369(18) 0.0362(18) -0.0151(15) 0.0256(15) -0.0106(14) B17A 0.0347(18) 0.0215(14) 0.051(2) 0.0083(14) 0.0323(18) 0.0042(13) B18A 0.0209(14) 0.0427(19) 0.0230(14) 0.0024(13) 0.0142(13) 0.0032(13) C39A 0.0200(13) 0.0242(13) 0.0200(13) 0.0041(10) 0.0127(12) 0.0015(10) C40A 0.0228(14) 0.0237(12) 0.0200(13) 0.0023(10) 0.0146(12) 0.0004(11) C41A 0.0227(14) 0.0265(14) 0.0237(14) 0.0011(11) 0.0146(12) -0.0016(11) C42A 0.0237(14) 0.0344(15) 0.0276(14) 0.0016(12) 0.0177(13) -0.0045(12) C43A 0.0284(15) 0.0358(15) 0.0370(17) 0.0034(13) 0.0261(15) 0.0026(12) C44A 0.0257(14) 0.0264(14) 0.0260(14) -0.0013(11) 0.0174(13) 0.0010(11) C45A 0.0186(13) 0.0212(13) 0.0267(14) -0.0041(10) 0.0153(12) 0.0001(10) C46A 0.0241(15) 0.0278(15) 0.0364(17) 0.0030(13) 0.0115(14) 0.0026(12) C47A 0.0286(18) 0.0213(15) 0.073(3) -0.0015(16) 0.0174(19) 0.0038(13) C48A 0.0304(18) 0.0323(17) 0.070(3) -0.0231(17) 0.0278(19) -0.0073(14) C49A 0.0337(16) 0.0416(18) 0.0328(16) -0.0156(14) 0.0206(14) -0.0085(14) C50A 0.0287(15) 0.0324(15) 0.0271(15) -0.0038(12) 0.0191(13) -0.0046(12) C51A 0.0288(15) 0.0249(14) 0.0274(15) -0.0076(11) 0.0208(13) -0.0081(11) C52A 0.062(2) 0.0231(14) 0.0456(19) -0.0011(13) 0.0444(19) -0.0036(14) C53A 0.105(4) 0.0210(15) 0.082(3) -0.0061(16) 0.083(3) -0.0078(18) C54A 0.089(3) 0.037(2) 0.086(3) -0.038(2) 0.075(3) -0.037(2) C55A 0.052(2) 0.068(3) 0.051(2) -0.039(2) 0.040(2) -0.029(2) C56A 0.0339(17) 0.0439(18) 0.0319(17) -0.0134(14) 0.0223(15) -0.0103(14) C57A 0.0197(13) 0.0207(10) 0.0193(10) -0.0020(8) 0.0124(11) -0.0017(10) Cl1 0.0620(16) 0.129(3) 0.110(3) 0.023(2) 0.0646(18) 0.0266(17) Cl2A 0.044(3) 0.096(6) 0.080(3) 0.040(5) 0.039(3) 0.008(3) Cl2B 0.044(3) 0.096(6) 0.080(3) 0.040(5) 0.039(3) 0.008(3) C58 0.055(4) 0.094(6) 0.031(3) -0.008(4) 0.036(4) 0.006(4) Cl3 0.165(3) 0.0946(16) 0.114(2) 0.0143(14) 0.100(2) 0.0220(17) Cl4 0.131(2) 0.164(2) 0.0950(19) 0.0059(18) 0.0802(19) -0.0394(19) C59 0.177(13) 0.30(2) 0.39(3) 0.24(2) 0.234(18) 0.110(14) Cl3B 0.165(3) 0.0946(16) 0.114(2) 0.0143(14) 0.100(2) 0.0220(17) Cl4B 0.131(2) 0.164(2) 0.0950(19) 0.0059(18) 0.0802(19) -0.0394(19) C59B 0.177(13) 0.30(2) 0.39(3) 0.24(2) 0.234(18) 0.110(14) Cl5 0.218(4) 0.0563(12) 0.290(5) 0.000 0.229(4) 0.000 Cl6 0.0710(13) 0.0628(12) 0.136(2) 0.000 0.0609(15) 0.000 C60 0.048(5) 0.086(6) 0.092(6) 0.003(7) 0.055(5) 0.007(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.398(4) . ? N1 C7 1.427(4) . ? N1 B1 1.433(4) . ? N2 C2 1.394(4) . ? N2 C13 1.422(4) . ? N2 B1 1.442(4) . ? N3 C19 1.397(4) . ? N3 B2 1.433(4) . ? N3 C25 1.445(4) . ? N4 C20 1.406(4) . ? N4 B2 1.436(4) . ? N4 C31 1.444(4) . ? B1 C37 1.582(4) . ? B2 C38 1.585(4) . ? B3 C37 1.715(5) . ? B3 B9 1.757(5) . ? B3 B7 1.763(6) . ? B3 B8 1.765(5) . ? B3 B4 1.779(5) . ? B3 H3 1.1200 . ? B4 C37 1.709(5) . ? B4 B5 1.759(5) . ? B4 B10 1.762(4) . ? B4 B9 1.771(5) . ? B4 H4 1.1200 . ? B5 C37 1.722(4) . ? B5 B10 1.742(5) . ? B5 B6 1.756(6) . ? B5 B11 1.757(5) . ? B5 H5 1.1200 . ? B6 C37 1.731(4) . ? B6 B11 1.742(5) . ? B6 B12 1.770(6) . ? B6 B7 1.772(6) . ? B6 H6 1.1200 . ? B7 C37 1.724(5) . ? B7 B8 1.757(6) . ? B7 B12 1.779(5) . ? B7 H7 1.1200 . ? B8 C38 1.719(4) . ? B8 B12 1.750(6) . ? B8 B9 1.773(6) . ? B8 H8 1.1200 . ? B9 C38 1.702(4) . ? B9 B10 1.765(5) . ? B9 H9 1.1200 . ? B10 C38 1.717(4) . ? B10 B11 1.748(5) . ? B10 H10 1.1200 . ? B11 C38 1.717(5) . ? B11 B12 1.765(6) . ? B11 H11 1.1200 . ? B12 C38 1.712(5) . ? B12 H12 1.1200 . ? C1 C2 1.389(5) . ? C1 C6 1.389(4) . ? C2 C3 1.395(5) . ? C3 C4 1.392(5) . ? C3 H3A 0.9500 . ? C4 C5 1.395(6) . ? C4 H4A 0.9500 . ? C5 C6 1.393(5) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C8 1.390(5) . ? C7 C12 1.393(5) . ? C8 C9 1.364(5) . ? C8 H8A 0.9500 . ? C9 C10 1.395(6) . ? C9 H9A 0.9500 . ? C10 C11 1.362(6) . ? C10 H10A 0.9500 . ? C11 C12 1.388(5) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C13 C18 1.384(5) . ? C13 C14 1.384(5) . ? C14 C15 1.385(7) . ? C14 H14 0.9500 . ? C15 C16 1.390(7) . ? C15 H15 0.9500 . ? C16 C17 1.405(7) . ? C16 H16 0.9500 . ? C17 C18 1.370(6) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C24 1.380(5) . ? C19 C20 1.400(5) . ? C20 C21 1.378(4) . ? C21 C22 1.387(5) . ? C21 H21 0.9500 . ? C22 C23 1.374(6) . ? C22 H22 0.9500 . ? C23 C24 1.385(5) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C26 1.364(5) . ? C25 C30 1.381(6) . ? C26 C27 1.413(6) . ? C26 H26 0.9500 . ? C27 C28 1.342(7) . ? C27 H27 0.9500 . ? C28 C29 1.370(8) . ? C28 H28 0.9500 . ? C29 C30 1.388(6) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 C36 1.377(4) . ? C31 C32 1.378(4) . ? C32 C33 1.392(5) . ? C32 H32 0.9500 . ? C33 C34 1.374(6) . ? C33 H33 0.9500 . ? C34 C35 1.387(6) . ? C34 H34 0.9500 . ? C35 C36 1.398(5) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? N5A C39A 1.399(4) . ? N5A B13A 1.431(4) . ? N5A C45A 1.435(4) . ? N6A C40A 1.407(4) . ? N6A C51A 1.423(4) . ? N6A B13A 1.432(4) . ? B13A C57A 1.587(3) . ? B14A C57A 1.736(4) . ? B14A B18A 1.754(5) . ? B14A B14A 1.755(6) 2_655 ? B14A B15A 1.755(5) 2_655 ? B14A B15A 1.772(5) . ? B14A H14A 1.1200 . ? B15A C57A 1.724(4) . ? B15A B14A 1.755(5) 2_655 ? B15A B16A 1.767(5) . ? B15A B18A 1.776(5) 2_655 ? B15A H15A 1.1200 . ? B16A C57A 1.722(4) . ? B16A B17A 1.753(5) 2_655 ? B16A B18A 1.767(5) 2_655 ? B16A B17A 1.781(6) . ? B16A H16A 1.1200 . ? B17A C57A 1.700(4) . ? B17A B16A 1.753(5) 2_655 ? B17A B17A 1.767(7) 2_655 ? B17A B18A 1.768(5) . ? B17A H17A 1.1200 . ? B18A C57A 1.694(5) . ? B18A B16A 1.766(5) 2_655 ? B18A B15A 1.776(5) 2_655 ? B18A H18A 1.1200 . ? C39A C44A 1.378(4) . ? C39A C40A 1.394(3) . ? C40A C41A 1.390(4) . ? C41A C42A 1.393(4) . ? C41A H41A 0.9500 . ? C42A C43A 1.379(4) . ? C42A H42A 0.9500 . ? C43A C44A 1.383(4) . ? C43A H43A 0.9500 . ? C44A H44A 0.9500 . ? C45A C46A 1.375(4) . ? C45A C50A 1.378(4) . ? C46A C47A 1.378(5) . ? C46A H46A 0.9500 . ? C47A C48A 1.380(6) . ? C47A H47A 0.9500 . ? C48A C49A 1.375(6) . ? C48A H48A 0.9500 . ? C49A C50A 1.390(4) . ? C49A H49A 0.9500 . ? C50A H50A 0.9500 . ? C51A C56A 1.382(5) . ? C51A C52A 1.385(5) . ? C52A C53A 1.391(5) . ? C52A H52A 0.9500 . ? C53A C54A 1.361(7) . ? C53A H53A 0.9500 . ? C54A C55A 1.359(7) . ? C54A H54A 0.9500 . ? C55A C56A 1.391(5) . ? C55A H55A 0.9500 . ? C56A H56A 0.9500 . ? Cl1 C58 1.667(9) . ? Cl2A C58 1.741(14) . ? Cl2B C58 1.689(14) . ? C58 H58A 0.9900 . ? C58 H58B 0.9900 . ? C58 H58C 0.9900 . ? C58 H58D 0.9900 . ? Cl3 C59 1.641(10) . ? Cl4 C59 1.635(9) . ? C59 H59C 0.9900 . ? C59 H59D 0.9900 . ? Cl3B C59B 1.619(18) . ? Cl4B C59B 1.622(19) . ? C59B H59A 0.9900 . ? C59B H59B 0.9900 . ? Cl5 C60 1.861(11) 2_655 ? Cl5 C60 1.861(11) . ? Cl6 C60 1.825(12) . ? Cl6 C60 1.825(11) 2_655 ? C60 H60A 0.9900 . ? C60 H60B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C7 117.5(3) . . ? C1 N1 B1 108.9(3) . . ? C7 N1 B1 133.6(3) . . ? C2 N2 C13 118.9(3) . . ? C2 N2 B1 108.0(3) . . ? C13 N2 B1 133.1(3) . . ? C19 N3 B2 108.8(3) . . ? C19 N3 C25 118.5(3) . . ? B2 N3 C25 132.7(3) . . ? C20 N4 B2 108.5(3) . . ? C20 N4 C31 117.3(2) . . ? B2 N4 C31 134.2(3) . . ? N1 B1 N2 105.5(3) . . ? N1 B1 C37 127.5(3) . . ? N2 B1 C37 126.8(3) . . ? N3 B2 N4 105.7(3) . . ? N3 B2 C38 126.7(3) . . ? N4 B2 C38 127.3(3) . . ? C37 B3 B9 105.3(2) . . ? C37 B3 B7 59.4(2) . . ? B9 B3 B7 108.0(2) . . ? C37 B3 B8 105.8(2) . . ? B9 B3 B8 60.4(2) . . ? B7 B3 B8 59.7(2) . . ? C37 B3 B4 58.52(19) . . ? B9 B3 B4 60.1(2) . . ? B7 B3 B4 108.0(2) . . ? B8 B3 B4 108.5(2) . . ? C37 B3 H3 124.1 . . ? B9 B3 H3 122.2 . . ? B7 B3 H3 121.6 . . ? B8 B3 H3 121.8 . . ? B4 B3 H3 121.5 . . ? C37 B4 B5 59.5(2) . . ? C37 B4 B10 105.4(3) . . ? B5 B4 B10 59.3(2) . . ? C37 B4 B9 105.0(2) . . ? B5 B4 B9 107.2(2) . . ? B10 B4 B9 59.9(2) . . ? C37 B4 B3 58.85(19) . . ? B5 B4 B3 107.8(3) . . ? B10 B4 B3 107.3(3) . . ? B9 B4 B3 59.3(2) . . ? C37 B4 H4 123.9 . . ? B5 B4 H4 121.8 . . ? B10 B4 H4 122.6 . . ? B9 B4 H4 122.8 . . ? B3 B4 H4 122.0 . . ? C37 B5 B10 105.7(2) . . ? C37 B5 B6 59.68(19) . . ? B10 B5 B6 107.6(3) . . ? C37 B5 B11 105.8(3) . . ? B10 B5 B11 60.0(2) . . ? B6 B5 B11 59.5(2) . . ? C37 B5 B4 58.78(18) . . ? B10 B5 B4 60.4(2) . . ? B6 B5 B4 108.3(3) . . ? B11 B5 B4 108.4(3) . . ? C37 B5 H5 123.8 . . ? B10 B5 H5 122.2 . . ? B6 B5 H5 121.6 . . ? B11 B5 H5 122.2 . . ? B4 B5 H5 121.2 . . ? C37 B6 B11 106.1(2) . . ? C37 B6 B5 59.18(19) . . ? B11 B6 B5 60.3(2) . . ? C37 B6 B12 106.0(3) . . ? B11 B6 B12 60.3(2) . . ? B5 B6 B12 108.6(3) . . ? C37 B6 B7 59.0(2) . . ? B11 B6 B7 108.6(3) . . ? B5 B6 B7 108.3(3) . . ? B12 B6 B7 60.3(2) . . ? C37 B6 H6 123.9 . . ? B11 B6 H6 121.8 . . ? B5 B6 H6 121.2 . . ? B12 B6 H6 121.8 . . ? B7 B6 H6 121.3 . . ? C37 B7 B8 105.8(3) . . ? C37 B7 B3 58.89(19) . . ? B8 B7 B3 60.2(2) . . ? C37 B7 B6 59.3(2) . . ? B8 B7 B6 107.2(2) . . ? B3 B7 B6 107.6(3) . . ? C37 B7 B12 105.9(3) . . ? B8 B7 B12 59.3(2) . . ? B3 B7 B12 107.6(3) . . ? B6 B7 B12 59.8(2) . . ? C37 B7 H7 123.6 . . ? B8 B7 H7 122.5 . . ? B3 B7 H7 121.7 . . ? B6 B7 H7 121.8 . . ? B12 B7 H7 122.5 . . ? C38 B8 B12 59.1(2) . . ? C38 B8 B7 106.1(3) . . ? B12 B8 B7 61.0(2) . . ? C38 B8 B3 105.2(2) . . ? B12 B8 B3 108.7(3) . . ? B7 B8 B3 60.1(2) . . ? C38 B8 B9 58.34(18) . . ? B12 B8 B9 107.5(3) . . ? B7 B8 B9 107.5(3) . . ? B3 B8 B9 59.5(2) . . ? C38 B8 H8 124.1 . . ? B12 B8 H8 121.0 . . ? B7 B8 H8 121.8 . . ? B3 B8 H8 122.2 . . ? B9 B8 H8 122.4 . . ? C38 B9 B3 106.3(3) . . ? C38 B9 B10 59.34(18) . . ? B3 B9 B10 108.2(2) . . ? C38 B9 B4 106.4(2) . . ? B3 B9 B4 60.6(2) . . ? B10 B9 B4 59.79(19) . . ? C38 B9 B8 59.2(2) . . ? B3 B9 B8 60.0(2) . . ? B10 B9 B8 108.1(3) . . ? B4 B9 B8 108.5(3) . . ? C38 B9 H9 123.4 . . ? B3 B9 H9 121.9 . . ? B10 B9 H9 121.6 . . ? B4 B9 H9 121.8 . . ? B8 B9 H9 121.4 . . ? C38 B10 B5 106.5(3) . . ? C38 B10 B11 59.40(19) . . ? B5 B10 B11 60.4(2) . . ? C38 B10 B4 106.1(3) . . ? B5 B10 B4 60.26(19) . . ? B11 B10 B4 108.7(3) . . ? C38 B10 B9 58.53(19) . . ? B5 B10 B9 108.3(2) . . ? B11 B10 B9 107.8(3) . . ? B4 B10 B9 60.3(2) . . ? C38 B10 H10 123.7 . . ? B5 B10 H10 121.7 . . ? B11 B10 H10 121.3 . . ? B4 B10 H10 121.7 . . ? B9 B10 H10 121.8 . . ? C38 B11 B6 105.9(3) . . ? C38 B11 B10 59.39(19) . . ? B6 B11 B10 107.9(2) . . ? C38 B11 B5 105.8(2) . . ? B6 B11 B5 60.2(2) . . ? B10 B11 B5 59.6(2) . . ? C38 B11 B12 58.9(2) . . ? B6 B11 B12 60.6(2) . . ? B10 B11 B12 108.3(3) . . ? B5 B11 B12 108.8(2) . . ? C38 B11 H11 123.9 . . ? B6 B11 H11 121.9 . . ? B10 B11 H11 121.6 . . ? B5 B11 H11 122.0 . . ? B12 B11 H11 121.1 . . ? C38 B12 B8 59.5(2) . . ? C38 B12 B11 59.2(2) . . ? B8 B12 B11 108.3(3) . . ? C38 B12 B6 104.9(3) . . ? B8 B12 B6 107.6(3) . . ? B11 B12 B6 59.0(2) . . ? C38 B12 B7 105.5(3) . . ? B8 B12 B7 59.7(2) . . ? B11 B12 B7 107.3(3) . . ? B6 B12 B7 59.9(2) . . ? C38 B12 H12 123.9 . . ? B8 B12 H12 121.3 . . ? B11 B12 H12 121.9 . . ? B6 B12 H12 122.9 . . ? B7 B12 H12 122.5 . . ? C2 C1 C6 122.0(3) . . ? C2 C1 N1 108.2(3) . . ? C6 C1 N1 129.9(3) . . ? C1 C2 N2 109.4(3) . . ? C1 C2 C3 121.0(3) . . ? N2 C2 C3 129.5(3) . . ? C4 C3 C2 117.3(4) . . ? C4 C3 H3A 121.4 . . ? C2 C3 H3A 121.4 . . ? C3 C4 C5 121.4(3) . . ? C3 C4 H4A 119.3 . . ? C5 C4 H4A 119.3 . . ? C6 C5 C4 121.3(3) . . ? C6 C5 H5A 119.3 . . ? C4 C5 H5A 119.3 . . ? C1 C6 C5 117.0(4) . . ? C1 C6 H6A 121.5 . . ? C5 C6 H6A 121.5 . . ? C8 C7 C12 120.5(3) . . ? C8 C7 N1 120.8(3) . . ? C12 C7 N1 118.6(3) . . ? C9 C8 C7 119.4(3) . . ? C9 C8 H8A 120.3 . . ? C7 C8 H8A 120.3 . . ? C8 C9 C10 120.3(4) . . ? C8 C9 H9A 119.8 . . ? C10 C9 H9A 119.8 . . ? C11 C10 C9 120.4(4) . . ? C11 C10 H10A 119.8 . . ? C9 C10 H10A 119.8 . . ? C10 C11 C12 120.2(4) . . ? C10 C11 H11A 119.9 . . ? C12 C11 H11A 119.9 . . ? C11 C12 C7 119.1(4) . . ? C11 C12 H12A 120.4 . . ? C7 C12 H12A 120.4 . . ? C18 C13 C14 120.2(4) . . ? C18 C13 N2 120.3(3) . . ? C14 C13 N2 119.5(3) . . ? C13 C14 C15 120.0(4) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C16 119.9(4) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C17 119.6(4) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C18 C17 C16 119.7(4) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C17 C18 C13 120.6(4) . . ? C17 C18 H18 119.7 . . ? C13 C18 H18 119.7 . . ? C24 C19 N3 130.7(3) . . ? C24 C19 C20 120.7(3) . . ? N3 C19 C20 108.6(3) . . ? C21 C20 C19 121.4(3) . . ? C21 C20 N4 130.3(3) . . ? C19 C20 N4 108.3(3) . . ? C20 C21 C22 117.5(3) . . ? C20 C21 H21 121.3 . . ? C22 C21 H21 121.3 . . ? C23 C22 C21 121.2(3) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C22 C23 C24 121.8(3) . . ? C22 C23 H23 119.1 . . ? C24 C23 H23 119.1 . . ? C19 C24 C23 117.5(3) . . ? C19 C24 H24 121.2 . . ? C23 C24 H24 121.2 . . ? C26 C25 C30 120.3(3) . . ? C26 C25 N3 120.1(3) . . ? C30 C25 N3 119.6(3) . . ? C25 C26 C27 118.9(4) . . ? C25 C26 H26 120.6 . . ? C27 C26 H26 120.6 . . ? C28 C27 C26 120.3(4) . . ? C28 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? C27 C28 C29 121.2(4) . . ? C27 C28 H28 119.4 . . ? C29 C28 H28 119.4 . . ? C28 C29 C30 119.3(5) . . ? C28 C29 H29 120.4 . . ? C30 C29 H29 120.4 . . ? C25 C30 C29 120.1(4) . . ? C25 C30 H30 120.0 . . ? C29 C30 H30 120.0 . . ? C36 C31 C32 120.7(3) . . ? C36 C31 N4 119.6(3) . . ? C32 C31 N4 119.6(3) . . ? C31 C32 C33 119.5(3) . . ? C31 C32 H32 120.2 . . ? C33 C32 H32 120.2 . . ? C34 C33 C32 120.5(3) . . ? C34 C33 H33 119.7 . . ? C32 C33 H33 119.7 . . ? C33 C34 C35 119.7(3) . . ? C33 C34 H34 120.1 . . ? C35 C34 H34 120.1 . . ? C34 C35 C36 120.0(4) . . ? C34 C35 H35 120.0 . . ? C36 C35 H35 120.0 . . ? C31 C36 C35 119.4(3) . . ? C31 C36 H36 120.3 . . ? C35 C36 H36 120.3 . . ? B1 C37 B4 117.1(2) . . ? B1 C37 B3 120.6(2) . . ? B4 C37 B3 62.6(2) . . ? B1 C37 B5 116.8(2) . . ? B4 C37 B5 61.7(2) . . ? B3 C37 B5 112.5(2) . . ? B1 C37 B7 121.5(2) . . ? B4 C37 B7 113.2(2) . . ? B3 C37 B7 61.7(2) . . ? B5 C37 B7 112.2(2) . . ? B1 C37 B6 119.7(3) . . ? B4 C37 B6 111.9(2) . . ? B3 C37 B6 111.8(2) . . ? B5 C37 B6 61.1(2) . . ? B7 C37 B6 61.7(2) . . ? B2 C38 B9 117.2(2) . . ? B2 C38 B12 122.1(2) . . ? B9 C38 B12 112.7(2) . . ? B2 C38 B10 115.7(2) . . ? B9 C38 B10 62.1(2) . . ? B12 C38 B10 112.3(3) . . ? B2 C38 B11 118.8(2) . . ? B9 C38 B11 112.2(2) . . ? B12 C38 B11 62.0(2) . . ? B10 C38 B11 61.2(2) . . ? B2 C38 B8 121.5(3) . . ? B9 C38 B8 62.4(2) . . ? B12 C38 B8 61.3(2) . . ? B10 C38 B8 112.9(2) . . ? B11 C38 B8 112.0(3) . . ? C39A N5A B13A 109.3(2) . . ? C39A N5A C45A 116.8(2) . . ? B13A N5A C45A 133.8(2) . . ? C40A N6A C51A 116.9(2) . . ? C40A N6A B13A 108.1(2) . . ? C51A N6A B13A 135.0(2) . . ? N5A B13A N6A 105.7(2) . . ? N5A B13A C57A 127.5(3) . . ? N6A B13A C57A 126.8(3) . . ? C57A B14A B18A 58.07(19) . . ? C57A B14A B14A 105.09(19) . 2_655 ? B18A B14A B14A 109.1(2) . 2_655 ? C57A B14A B15A 105.1(2) . 2_655 ? B18A B14A B15A 60.81(19) . 2_655 ? B14A B14A B15A 60.6(2) 2_655 2_655 ? C57A B14A B15A 58.86(19) . . ? B18A B14A B15A 107.7(2) . . ? B14A B14A B15A 59.7(2) 2_655 . ? B15A B14A B15A 108.1(2) 2_655 . ? C57A B14A H14A 124.8 . . ? B18A B14A H14A 121.3 . . ? B14A B14A H14A 121.8 2_655 . ? B15A B14A H14A 121.8 2_655 . ? B15A B14A H14A 121.8 . . ? C57A B15A B14A 105.6(2) . 2_655 ? C57A B15A B16A 59.12(19) . . ? B14A B15A B16A 107.9(2) 2_655 . ? C57A B15A B14A 59.53(18) . . ? B14A B15A B14A 59.7(2) 2_655 . ? B16A B15A B14A 108.4(2) . . ? C57A B15A B18A 105.1(2) . 2_655 ? B14A B15A B18A 59.56(18) 2_655 2_655 ? B16A B15A B18A 59.82(19) . 2_655 ? B14A B15A B18A 107.3(2) . 2_655 ? C57A B15A H15A 123.8 . . ? B14A B15A H15A 122.4 2_655 . ? B16A B15A H15A 121.4 . . ? B14A B15A H15A 121.5 . . ? B18A B15A H15A 122.8 2_655 . ? C57A B16A B17A 105.1(2) . 2_655 ? C57A B16A B18A 105.6(2) . 2_655 ? B17A B16A B18A 60.3(2) 2_655 2_655 ? C57A B16A B15A 59.20(18) . . ? B17A B16A B15A 108.6(2) 2_655 . ? B18A B16A B15A 60.3(2) 2_655 . ? C57A B16A B17A 58.02(19) . . ? B17A B16A B17A 60.0(2) 2_655 . ? B18A B16A B17A 107.9(2) 2_655 . ? B15A B16A B17A 107.5(2) . . ? C57A B16A H16A 124.4 . . ? B17A B16A H16A 122.0 2_655 . ? B18A B16A H16A 121.9 2_655 . ? B15A B16A H16A 121.2 . . ? B17A B16A H16A 122.1 . . ? C57A B17A B16A 105.5(2) . 2_655 ? C57A B17A B17A 105.4(2) . 2_655 ? B16A B17A B17A 60.8(2) 2_655 2_655 ? C57A B17A B18A 58.43(19) . . ? B16A B17A B18A 60.2(2) 2_655 . ? B17A B17A B18A 108.5(2) 2_655 . ? C57A B17A B16A 59.3(2) . . ? B16A B17A B16A 107.9(2) 2_655 . ? B17A B17A B16A 59.2(2) 2_655 . ? B18A B17A B16A 107.6(2) . . ? C57A B17A H17A 124.2 . . ? B16A B17A H17A 121.8 2_655 . ? B17A B17A H17A 122.0 2_655 . ? B18A B17A H17A 121.6 . . ? B16A B17A H17A 121.9 . . ? C57A B18A B14A 60.43(18) . . ? C57A B18A B16A 105.2(2) . 2_655 ? B14A B18A B16A 107.9(2) . 2_655 ? C57A B18A B17A 58.77(19) . . ? B14A B18A B17A 108.8(2) . . ? B16A B18A B17A 59.5(2) 2_655 . ? C57A B18A B15A 106.0(2) . 2_655 ? B14A B18A B15A 59.6(2) . 2_655 ? B16A B18A B15A 59.8(2) 2_655 2_655 ? B17A B18A B15A 107.5(2) . 2_655 ? C57A B18A H18A 123.5 . . ? B14A B18A H18A 120.9 . . ? B16A B18A H18A 122.7 2_655 . ? B17A B18A H18A 121.7 . . ? B15A B18A H18A 122.5 2_655 . ? C44A C39A C40A 121.1(3) . . ? C44A C39A N5A 131.0(3) . . ? C40A C39A N5A 107.8(3) . . ? C41A C40A C39A 121.0(3) . . ? C41A C40A N6A 130.0(3) . . ? C39A C40A N6A 109.1(3) . . ? C40A C41A C42A 117.3(3) . . ? C40A C41A H41A 121.4 . . ? C42A C41A H41A 121.4 . . ? C43A C42A C41A 121.4(3) . . ? C43A C42A H42A 119.3 . . ? C41A C42A H42A 119.3 . . ? C42A C43A C44A 121.2(3) . . ? C42A C43A H43A 119.4 . . ? C44A C43A H43A 119.4 . . ? C39A C44A C43A 118.0(3) . . ? C39A C44A H44A 121.0 . . ? C43A C44A H44A 121.0 . . ? C46A C45A C50A 120.7(3) . . ? C46A C45A N5A 120.0(3) . . ? C50A C45A N5A 119.2(3) . . ? C45A C46A C47A 120.0(3) . . ? C45A C46A H46A 120.0 . . ? C47A C46A H46A 120.0 . . ? C46A C47A C48A 120.0(3) . . ? C46A C47A H47A 120.0 . . ? C48A C47A H47A 120.0 . . ? C49A C48A C47A 119.7(3) . . ? C49A C48A H48A 120.1 . . ? C47A C48A H48A 120.1 . . ? C48A C49A C50A 120.6(3) . . ? C48A C49A H49A 119.7 . . ? C50A C49A H49A 119.7 . . ? C45A C50A C49A 118.9(3) . . ? C45A C50A H50A 120.5 . . ? C49A C50A H50A 120.5 . . ? C56A C51A C52A 121.2(3) . . ? C56A C51A N6A 119.7(3) . . ? C52A C51A N6A 119.0(3) . . ? C51A C52A C53A 117.8(4) . . ? C51A C52A H52A 121.1 . . ? C53A C52A H52A 121.1 . . ? C54A C53A C52A 121.7(4) . . ? C54A C53A H53A 119.1 . . ? C52A C53A H53A 119.1 . . ? C55A C54A C53A 119.8(3) . . ? C55A C54A H54A 120.1 . . ? C53A C54A H54A 120.1 . . ? C54A C55A C56A 120.8(4) . . ? C54A C55A H55A 119.6 . . ? C56A C55A H55A 119.6 . . ? C51A C56A C55A 118.7(4) . . ? C51A C56A H56A 120.6 . . ? C55A C56A H56A 120.6 . . ? B13A C57A B18A 117.7(3) . . ? B13A C57A B17A 117.8(2) . . ? B18A C57A B17A 62.8(2) . . ? B13A C57A B16A 119.1(2) . . ? B18A C57A B16A 113.9(2) . . ? B17A C57A B16A 62.7(2) . . ? B13A C57A B15A 119.5(3) . . ? B18A C57A B15A 112.8(2) . . ? B17A C57A B15A 113.4(2) . . ? B16A C57A B15A 61.7(2) . . ? B13A C57A B14A 119.4(2) . . ? B18A C57A B14A 61.5(2) . . ? B17A C57A B14A 112.9(2) . . ? B16A C57A B14A 112.2(2) . . ? B15A C57A B14A 61.6(2) . . ? Cl1 C58 Cl2B 113.4(6) . . ? Cl1 C58 Cl2A 111.9(6) . . ? Cl2B C58 Cl2A 17.0(4) . . ? Cl1 C58 H58A 109.2 . . ? Cl2B C58 H58A 93.4 . . ? Cl2A C58 H58A 109.2 . . ? Cl1 C58 H58B 109.2 . . ? Cl2B C58 H58B 121.8 . . ? Cl2A C58 H58B 109.2 . . ? H58A C58 H58B 107.9 . . ? Cl1 C58 H58C 108.9 . . ? Cl2B C58 H58C 108.9 . . ? Cl2A C58 H58C 123.3 . . ? H58A C58 H58C 17.7 . . ? H58B C58 H58C 92.0 . . ? Cl1 C58 H58D 108.9 . . ? Cl2B C58 H58D 108.9 . . ? Cl2A C58 H58D 94.4 . . ? H58A C58 H58D 122.3 . . ? H58B C58 H58D 17.1 . . ? H58C C58 H58D 107.7 . . ? Cl4 C59 Cl3 122.4(8) . . ? Cl4 C59 H59C 106.7 . . ? Cl3 C59 H59C 106.7 . . ? Cl4 C59 H59D 106.7 . . ? Cl3 C59 H59D 106.7 . . ? H59C C59 H59D 106.6 . . ? Cl3B C59B Cl4B 118(2) . . ? Cl3B C59B H59A 107.7 . . ? Cl4B C59B H59A 107.7 . . ? Cl3B C59B H59B 107.7 . . ? Cl4B C59B H59B 107.7 . . ? H59A C59B H59B 107.1 . . ? C60 Cl5 C60 78.1(7) 2_655 . ? C60 Cl6 C60 79.9(7) . 2_655 ? Cl6 C60 Cl5 101.0(5) . . ? Cl6 C60 H60A 111.6 . . ? Cl5 C60 H60A 111.6 . . ? Cl6 C60 H60B 111.6 . . ? Cl5 C60 H60B 111.6 . . ? H60A C60 H60B 109.4 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.175 _refine_diff_density_min -0.741 _refine_diff_density_rms 0.077 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound23 _database_code_depnum_ccdc_archive 'CCDC 929986' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H23 B N2' _chemical_formula_sum 'C22 H23 B N2' _chemical_formula_weight 326.23 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' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R -3' _symmetry_space_group_name_Hall '-R 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 18.3607(6) _cell_length_b 18.3607(6) _cell_length_c 27.8834(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 8140.6(5) _cell_formula_units_Z 18 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7117 _cell_measurement_theta_min 2.664 _cell_measurement_theta_max 23.317 _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.198 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3132 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9858 _exptl_absorpt_correction_T_max 0.9929 _exptl_absorpt_process_details 'SADABS 2008/1 (Bruker AXS, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_measurement_device 'Bruker KAPPA APEX II ' _diffrn_radiation_source 'fine focus sealed tube ' _diffrn_radiation_monochromator 'graphite monochromator ' _diffrn_measurement_device_type 'four three circle diffractometer' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 64555 _diffrn_reflns_av_R_equivalents 0.0939 _diffrn_reflns_av_sigmaI/netI 0.0557 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 30.00 _reflns_number_total 5272 _reflns_number_gt 3323 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2009.11-0 (Bruker AXS, 2009)' _computing_cell_refinement 'APEX2 v2009.11-0 (Bruker AXS, 2009)' _computing_data_reduction 'SAINT (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND 2.1 (Crystal Impact, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0451P)^2^+11.6740P] 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 5272 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1024 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1238 _refine_ls_wR_factor_gt 0.0992 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 N1 N 0.34377(7) 0.34326(7) 0.08770(4) 0.0152(3) Uani 1 1 d . . . N2 N 0.32977(8) 0.21260(8) 0.08081(4) 0.0163(3) Uani 1 1 d . . . B1 B 0.39202(10) 0.30116(10) 0.08099(6) 0.0161(3) Uani 1 1 d . . . C1 C 0.25773(9) 0.28295(9) 0.08916(5) 0.0150(3) Uani 1 1 d . . . C2 C 0.24955(9) 0.20323(9) 0.08535(6) 0.0177(3) Uani 1 1 d . . . C3 C 0.17180(10) 0.13142(10) 0.08704(7) 0.0292(4) Uani 1 1 d . . . H3 H 0.1664 0.0773 0.0849 0.035 Uiso 1 1 calc R . . C4 C 0.10151(11) 0.14046(11) 0.09198(8) 0.0348(5) Uani 1 1 d . . . H4 H 0.0473 0.0917 0.0934 0.042 Uiso 1 1 calc R . . C5 C 0.10897(10) 0.21930(10) 0.09490(6) 0.0244(4) Uani 1 1 d . . . H5 H 0.0598 0.2238 0.0977 0.029 Uiso 1 1 calc R . . C6 C 0.18730(9) 0.29178(9) 0.09373(5) 0.0178(3) Uani 1 1 d . . . H6 H 0.1925 0.3458 0.0960 0.021 Uiso 1 1 calc R . . C7 C 0.36885(9) 0.42983(9) 0.09469(5) 0.0152(3) Uani 1 1 d . . . C8 C 0.34550(9) 0.47120(9) 0.06195(5) 0.0180(3) Uani 1 1 d . . . H8 H 0.3143 0.4426 0.0342 0.022 Uiso 1 1 calc R . . C9 C 0.36770(10) 0.55444(10) 0.06976(6) 0.0204(3) Uani 1 1 d . . . H9 H 0.3512 0.5826 0.0474 0.024 Uiso 1 1 calc R . . C10 C 0.41382(9) 0.59677(9) 0.11002(6) 0.0199(3) Uani 1 1 d . . . H10 H 0.4291 0.6538 0.1152 0.024 Uiso 1 1 calc R . . C11 C 0.43744(9) 0.55537(9) 0.14259(6) 0.0192(3) Uani 1 1 d . . . H11 H 0.4695 0.5844 0.1700 0.023 Uiso 1 1 calc R . . C12 C 0.41444(9) 0.47166(9) 0.13531(5) 0.0165(3) Uani 1 1 d . . . H12 H 0.4298 0.4432 0.1580 0.020 Uiso 1 1 calc R . . C13 C 0.33709(9) 0.13853(9) 0.07868(5) 0.0165(3) Uani 1 1 d . . . C14 C 0.37142(9) 0.11772(10) 0.11702(6) 0.0192(3) Uani 1 1 d . . . H14 H 0.3913 0.1532 0.1444 0.023 Uiso 1 1 calc R . . C15 C 0.37670(10) 0.04494(10) 0.11530(6) 0.0214(3) Uani 1 1 d . . . H15 H 0.4012 0.0312 0.1413 0.026 Uiso 1 1 calc R . . C16 C 0.34636(10) -0.00776(10) 0.07584(6) 0.0218(3) Uani 1 1 d . . . H16 H 0.3497 -0.0577 0.0748 0.026 Uiso 1 1 calc R . . C17 C 0.31122(10) 0.01254(9) 0.03787(6) 0.0203(3) Uani 1 1 d . . . H17 H 0.2901 -0.0238 0.0109 0.024 Uiso 1 1 calc R . . C18 C 0.30665(9) 0.08580(9) 0.03904(5) 0.0179(3) Uani 1 1 d . . . H18 H 0.2828 0.0998 0.0129 0.022 Uiso 1 1 calc R . . C19 C 0.48996(9) 0.34264(9) 0.07113(6) 0.0183(3) Uani 1 1 d . . . C20 C 0.52446(10) 0.42843(10) 0.04653(6) 0.0247(4) Uani 1 1 d . . . H20A H 0.5190 0.4674 0.0682 0.037 Uiso 1 1 calc R . . H20B H 0.4925 0.4219 0.0171 0.037 Uiso 1 1 calc R . . H20C H 0.5839 0.4508 0.0385 0.037 Uiso 1 1 calc R . . C21 C 0.53860(11) 0.35445(12) 0.11799(7) 0.0321(4) Uani 1 1 d . . . H21A H 0.5986 0.3791 0.1109 0.048 Uiso 1 1 calc R . . H21B H 0.5179 0.2998 0.1336 0.048 Uiso 1 1 calc R . . H21C H 0.5303 0.3920 0.1394 0.048 Uiso 1 1 calc R . . C22 C 0.50794(11) 0.28752(10) 0.03711(7) 0.0272(4) Uani 1 1 d . . . H22A H 0.4759 0.2779 0.0074 0.041 Uiso 1 1 calc R . . H22B H 0.4912 0.2335 0.0526 0.041 Uiso 1 1 calc R . . H22C H 0.5682 0.3161 0.0297 0.041 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 N1 0.0136(6) 0.0122(6) 0.0189(6) -0.0016(5) -0.0005(5) 0.0058(5) N2 0.0152(6) 0.0144(6) 0.0215(7) 0.0005(5) 0.0007(5) 0.0090(5) B1 0.0160(8) 0.0158(8) 0.0160(8) -0.0009(6) -0.0007(6) 0.0075(7) C1 0.0135(7) 0.0154(7) 0.0154(7) 0.0006(5) 0.0003(5) 0.0066(6) C2 0.0142(7) 0.0171(7) 0.0233(8) 0.0014(6) 0.0007(6) 0.0089(6) C3 0.0177(8) 0.0135(7) 0.0570(12) 0.0019(7) 0.0028(8) 0.0084(6) C4 0.0136(8) 0.0166(8) 0.0699(14) 0.0022(8) 0.0032(8) 0.0043(7) C5 0.0145(7) 0.0222(8) 0.0388(10) 0.0014(7) 0.0017(7) 0.0110(7) C6 0.0178(7) 0.0169(7) 0.0218(8) -0.0005(6) -0.0006(6) 0.0109(6) C7 0.0132(7) 0.0139(7) 0.0185(7) -0.0007(5) 0.0028(5) 0.0068(6) C8 0.0179(7) 0.0183(7) 0.0171(8) -0.0026(6) -0.0019(6) 0.0086(6) C9 0.0227(8) 0.0184(7) 0.0218(8) 0.0014(6) 0.0003(6) 0.0115(6) C10 0.0180(7) 0.0139(7) 0.0270(8) -0.0010(6) 0.0022(6) 0.0074(6) C11 0.0151(7) 0.0180(7) 0.0224(8) -0.0052(6) -0.0021(6) 0.0066(6) C12 0.0132(7) 0.0167(7) 0.0196(8) -0.0001(6) -0.0001(5) 0.0074(6) C13 0.0147(7) 0.0147(7) 0.0215(8) 0.0031(6) 0.0041(6) 0.0083(6) C14 0.0194(7) 0.0213(8) 0.0192(8) 0.0002(6) 0.0008(6) 0.0119(6) C15 0.0222(8) 0.0242(8) 0.0231(8) 0.0061(6) 0.0020(6) 0.0155(7) C16 0.0229(8) 0.0185(8) 0.0278(9) 0.0043(6) 0.0068(7) 0.0130(7) C17 0.0215(8) 0.0173(7) 0.0216(8) -0.0010(6) 0.0037(6) 0.0095(6) C18 0.0180(7) 0.0174(7) 0.0184(8) 0.0020(6) 0.0010(6) 0.0088(6) C19 0.0149(7) 0.0165(7) 0.0228(8) -0.0017(6) 0.0020(6) 0.0073(6) C20 0.0177(8) 0.0180(8) 0.0353(10) 0.0011(7) 0.0079(7) 0.0067(6) C21 0.0174(8) 0.0425(11) 0.0337(10) -0.0024(8) -0.0042(7) 0.0131(8) C22 0.0210(8) 0.0200(8) 0.0410(10) -0.0007(7) 0.0107(7) 0.0105(7) _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 N1 C1 1.4051(18) . ? N1 C7 1.4298(18) . ? N1 B1 1.450(2) . ? N2 C2 1.4006(18) . ? N2 C13 1.4332(18) . ? N2 B1 1.446(2) . ? B1 C19 1.587(2) . ? C1 C6 1.387(2) . ? C1 C2 1.399(2) . ? C2 C3 1.377(2) . ? C3 C4 1.388(2) . ? C3 H3 0.9500 . ? C4 C5 1.387(2) . ? C4 H4 0.9500 . ? C5 C6 1.388(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.386(2) . ? C7 C12 1.389(2) . ? C8 C9 1.388(2) . ? C8 H8 0.9500 . ? C9 C10 1.387(2) . ? C9 H9 0.9500 . ? C10 C11 1.386(2) . ? C10 H10 0.9500 . ? C11 C12 1.390(2) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.388(2) . ? C13 C18 1.389(2) . ? C14 C15 1.388(2) . ? C14 H14 0.9500 . ? C15 C16 1.385(2) . ? C15 H15 0.9500 . ? C16 C17 1.384(2) . ? C16 H16 0.9500 . ? C17 C18 1.389(2) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.535(2) . ? C19 C21 1.536(2) . ? C19 C22 1.538(2) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C7 118.84(11) . . ? C1 N1 B1 109.24(12) . . ? C7 N1 B1 131.86(12) . . ? C2 N2 C13 118.62(12) . . ? C2 N2 B1 109.22(12) . . ? C13 N2 B1 132.12(12) . . ? N2 B1 N1 104.47(12) . . ? N2 B1 C19 127.42(13) . . ? N1 B1 C19 127.89(13) . . ? C6 C1 C2 120.71(13) . . ? C6 C1 N1 131.08(13) . . ? C2 C1 N1 108.22(12) . . ? C3 C2 C1 121.11(14) . . ? C3 C2 N2 130.09(14) . . ? C1 C2 N2 108.79(12) . . ? C2 C3 C4 118.02(15) . . ? C2 C3 H3 121.0 . . ? C4 C3 H3 121.0 . . ? C5 C4 C3 121.22(15) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 120.90(15) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C1 C6 C5 118.02(14) . . ? C1 C6 H6 121.0 . . ? C5 C6 H6 121.0 . . ? C8 C7 C12 120.01(13) . . ? C8 C7 N1 120.24(13) . . ? C12 C7 N1 119.72(13) . . ? C7 C8 C9 119.94(14) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 120.33(14) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C11 C10 C9 119.60(14) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 120.35(14) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C7 C12 C11 119.75(14) . . ? C7 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C14 C13 C18 120.05(14) . . ? C14 C13 N2 120.02(14) . . ? C18 C13 N2 119.88(13) . . ? C15 C14 C13 119.88(15) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C16 C15 C14 120.17(15) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C17 C16 C15 119.89(14) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 120.30(15) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C13 C18 C17 119.69(14) . . ? C13 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C20 C19 C21 108.83(13) . . ? C20 C19 C22 106.58(13) . . ? C21 C19 C22 108.46(14) . . ? C20 C19 B1 110.92(13) . . ? C21 C19 B1 111.08(13) . . ? C22 C19 B1 110.82(12) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.351 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.054 #===END