# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Kehr, Gerald' 'Erdmann, Markus' 'Erker, G.' 'Frohlich, Roland' 'Daniliuc, Constantin' 'Uhl, W.' 'Rosener, Christian' 'Wurthwein, Ernst' Holtrichter-Rossmann, Thorsten data_erk6557 _database_code_depnum_ccdc_archive 'CCDC 894610' #TrackingRef '- 6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H23 B F5 N' _chemical_formula_weight 371.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.7049(7) _cell_length_b 9.8068(2) _cell_length_c 13.6633(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.373(2) _cell_angle_gamma 90.00 _cell_volume 3705.84(18) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3064 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 0.956 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6896 _exptl_absorpt_correction_T_max 0.8468 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11474 _diffrn_reflns_av_R_equivalents 0.030 _diffrn_reflns_av_sigmaI/netI 0.0209 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 5.73 _diffrn_reflns_theta_max 66.98 _reflns_number_total 3167 _reflns_number_gt 3026 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _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^)+(0.0497P)^2^+2.3659P] 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 3167 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1013 _refine_ls_wR_factor_gt 0.1002 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.36492(5) -0.10654(16) 0.82169(11) 0.0331(3) Uani 1 1 d . . . N1 N 0.38304(4) -0.29780(11) 0.68061(8) 0.0378(3) Uani 1 1 d . . . C1 C 0.35413(5) -0.19614(14) 0.91952(10) 0.0374(3) Uani 1 1 d . . . H1 H 0.3838 -0.2474 0.9401 0.045 Uiso 1 1 calc R . . C2 C 0.34306(5) -0.09605(17) 1.00168(10) 0.0443(3) Uani 1 1 d . . . H2A H 0.3373 -0.1484 1.0609 0.053 Uiso 1 1 calc R . . H2B H 0.3717 -0.0391 1.0161 0.053 Uiso 1 1 calc R . . C3 C 0.29966(6) -0.00303(17) 0.97874(11) 0.0485(4) Uani 1 1 d . . . H3A H 0.3001 0.0701 1.0277 0.058 Uiso 1 1 calc R . . H3B H 0.2700 -0.0559 0.9851 0.058 Uiso 1 1 calc R . . C4 C 0.29814(5) 0.06117(15) 0.87644(11) 0.0427(3) Uani 1 1 d . . . H4A H 0.3189 0.1422 0.8795 0.051 Uiso 1 1 calc R . . H4B H 0.2650 0.0921 0.8602 0.051 Uiso 1 1 calc R . . C5 C 0.31386(5) -0.02968(14) 0.79144(10) 0.0357(3) Uani 1 1 d . . . H5 H 0.3185 0.0289 0.7337 0.043 Uiso 1 1 calc R . . C6 C 0.27531(5) -0.13824(16) 0.76296(11) 0.0433(3) Uani 1 1 d . . . H6A H 0.2447 -0.0920 0.7454 0.052 Uiso 1 1 calc R . . H6B H 0.2851 -0.1867 0.7046 0.052 Uiso 1 1 calc R . . C7 C 0.26688(5) -0.24300(17) 0.84353(11) 0.0471(4) Uani 1 1 d . . . H7A H 0.2474 -0.2004 0.8927 0.057 Uiso 1 1 calc R . . H7B H 0.2481 -0.3192 0.8145 0.057 Uiso 1 1 calc R . . C8 C 0.31324(5) -0.29947(15) 0.89505(11) 0.0445(3) Uani 1 1 d . . . H8A H 0.3259 -0.3709 0.8535 0.053 Uiso 1 1 calc R . . H8B H 0.3047 -0.3429 0.9563 0.053 Uiso 1 1 calc R . . C9 C 0.37596(5) -0.21502(14) 0.73713(10) 0.0358(3) Uani 1 1 d . . . C10 C 0.38957(5) -0.40985(14) 0.61158(11) 0.0408(3) Uani 1 1 d . . . C11 C 0.44347(7) -0.4373(2) 0.6106(2) 0.0813(7) Uani 1 1 d . . . H11A H 0.4597 -0.3566 0.5881 0.122 Uiso 1 1 calc R . . H11B H 0.4490 -0.5127 0.5667 0.122 Uiso 1 1 calc R . . H11C H 0.4561 -0.4603 0.6762 0.122 Uiso 1 1 calc R . . C12 C 0.36862(9) -0.3622(2) 0.51280(13) 0.0744(6) Uani 1 1 d . . . H12A H 0.3343 -0.3449 0.5165 0.112 Uiso 1 1 calc R . . H12B H 0.3734 -0.4321 0.4641 0.112 Uiso 1 1 calc R . . H12C H 0.3847 -0.2790 0.4944 0.112 Uiso 1 1 calc R . . C13 C 0.36248(7) -0.53127(17) 0.64899(14) 0.0607(5) Uani 1 1 d . . . H13A H 0.3748 -0.5530 0.7151 0.091 Uiso 1 1 calc R . . H13B H 0.3670 -0.6090 0.6066 0.091 Uiso 1 1 calc R . . H13C H 0.3283 -0.5097 0.6493 0.091 Uiso 1 1 calc R . . C21 C 0.41527(4) -0.01599(14) 0.83541(9) 0.0328(3) Uani 1 1 d . . . F22 F 0.38214(3) 0.20090(8) 0.79000(7) 0.0482(2) Uani 1 1 d . . . C22 C 0.41981(5) 0.12420(14) 0.82433(10) 0.0358(3) Uani 1 1 d . . . F23 F 0.46318(3) 0.33221(9) 0.83562(7) 0.0581(3) Uani 1 1 d . . . C23 C 0.46216(5) 0.19586(15) 0.84576(10) 0.0406(3) Uani 1 1 d . . . F24 F 0.54523(3) 0.19526(10) 0.89471(7) 0.0578(3) Uani 1 1 d . . . C24 C 0.50383(5) 0.12724(16) 0.87529(10) 0.0412(3) Uani 1 1 d . . . F25 F 0.54302(3) -0.08215(10) 0.90750(7) 0.0531(3) Uani 1 1 d . . . C25 C 0.50227(5) -0.01226(16) 0.88209(10) 0.0393(3) Uani 1 1 d . . . F26 F 0.46082(3) -0.21684(8) 0.87071(7) 0.0487(2) Uani 1 1 d . . . C26 C 0.45896(5) -0.07895(14) 0.86288(10) 0.0366(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0330(7) 0.0332(8) 0.0334(7) 0.0001(6) 0.0044(6) -0.0013(6) N1 0.0407(6) 0.0334(6) 0.0398(6) -0.0011(5) 0.0052(5) -0.0012(5) C1 0.0345(7) 0.0413(7) 0.0366(7) 0.0066(6) 0.0036(5) -0.0001(5) C2 0.0464(8) 0.0541(9) 0.0324(7) 0.0019(6) 0.0036(6) -0.0053(7) C3 0.0523(8) 0.0509(9) 0.0433(8) -0.0055(7) 0.0129(6) -0.0017(7) C4 0.0383(7) 0.0417(8) 0.0487(8) 0.0000(6) 0.0087(6) 0.0044(6) C5 0.0338(7) 0.0384(7) 0.0350(7) 0.0037(5) 0.0026(5) -0.0001(5) C6 0.0350(7) 0.0526(9) 0.0419(8) -0.0010(6) -0.0014(6) -0.0035(6) C7 0.0401(7) 0.0522(9) 0.0492(8) -0.0025(7) 0.0035(6) -0.0145(7) C8 0.0473(8) 0.0419(8) 0.0449(8) 0.0060(6) 0.0092(6) -0.0079(6) C9 0.0347(7) 0.0351(7) 0.0376(7) 0.0048(6) 0.0036(5) -0.0031(5) C10 0.0477(8) 0.0315(7) 0.0438(8) -0.0059(6) 0.0078(6) 0.0002(6) C11 0.0530(11) 0.0630(12) 0.130(2) -0.0316(12) 0.0196(11) 0.0063(9) C12 0.1200(17) 0.0600(11) 0.0428(9) -0.0029(8) 0.0007(10) 0.0003(11) C13 0.0798(12) 0.0392(8) 0.0640(11) -0.0022(8) 0.0110(9) -0.0133(8) C21 0.0344(7) 0.0349(7) 0.0297(6) 0.0004(5) 0.0070(5) -0.0001(5) F22 0.0429(5) 0.0383(5) 0.0634(5) 0.0129(4) 0.0027(4) 0.0024(3) C22 0.0356(7) 0.0374(7) 0.0349(7) 0.0030(5) 0.0063(5) 0.0007(5) F23 0.0619(6) 0.0380(5) 0.0749(6) 0.0052(4) 0.0069(5) -0.0140(4) C23 0.0480(8) 0.0366(7) 0.0381(7) 0.0003(6) 0.0099(6) -0.0089(6) F24 0.0442(5) 0.0688(6) 0.0599(6) -0.0043(5) -0.0001(4) -0.0220(4) C24 0.0362(7) 0.0531(9) 0.0347(7) -0.0026(6) 0.0055(5) -0.0128(6) F25 0.0329(4) 0.0668(6) 0.0591(5) 0.0005(4) -0.0006(4) 0.0061(4) C25 0.0326(7) 0.0523(9) 0.0331(7) -0.0010(6) 0.0039(5) 0.0016(6) F26 0.0411(4) 0.0369(5) 0.0682(6) 0.0021(4) 0.0027(4) 0.0061(3) C26 0.0369(7) 0.0362(7) 0.0373(7) -0.0002(5) 0.0069(5) 0.0007(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 B1 C9 1.613(2) . ? B1 C5 1.6345(19) . ? B1 C1 1.6417(19) . ? B1 C21 1.6550(19) . ? N1 C9 1.1454(18) . ? N1 C10 1.4662(17) . ? C1 C2 1.536(2) . ? C1 C8 1.5418(19) . ? C1 H1 0.9900 . ? C2 C3 1.527(2) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 C4 1.531(2) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C4 C5 1.5466(19) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C5 C6 1.5417(19) . ? C5 H5 0.9900 . ? C6 C7 1.534(2) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C7 C8 1.532(2) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C10 C12 1.512(2) . ? C10 C13 1.513(2) . ? C10 C11 1.518(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 H11C 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 H12C 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13 H13C 0.9700 . ? C21 C22 1.390(2) . ? C21 C26 1.3904(18) . ? F22 C22 1.3481(15) . ? C22 C23 1.3841(19) . ? F23 C23 1.3448(17) . ? C23 C24 1.376(2) . ? F24 C24 1.3398(15) . ? C24 C25 1.372(2) . ? F25 C25 1.3485(16) . ? C25 C26 1.3783(19) . ? F26 C26 1.3573(16) . ? 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 C9 B1 C5 108.70(11) . . ? C9 B1 C1 106.35(11) . . ? C5 B1 C1 104.85(10) . . ? C9 B1 C21 103.95(10) . . ? C5 B1 C21 119.50(11) . . ? C1 B1 C21 112.82(11) . . ? C9 N1 C10 175.90(13) . . ? C2 C1 C8 113.76(11) . . ? C2 C1 B1 107.87(11) . . ? C8 C1 B1 110.00(11) . . ? C2 C1 H1 108.4 . . ? C8 C1 H1 108.4 . . ? B1 C1 H1 108.4 . . ? C3 C2 C1 114.86(12) . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2A 108.6 . . ? C3 C2 H2B 108.6 . . ? C1 C2 H2B 108.6 . . ? H2A C2 H2B 107.5 . . ? C2 C3 C4 114.33(12) . . ? C2 C3 H3A 108.7 . . ? C4 C3 H3A 108.7 . . ? C2 C3 H3B 108.7 . . ? C4 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? C3 C4 C5 117.05(12) . . ? C3 C4 H4A 108.0 . . ? C5 C4 H4A 108.0 . . ? C3 C4 H4B 108.0 . . ? C5 C4 H4B 108.0 . . ? H4A C4 H4B 107.3 . . ? C6 C5 C4 111.46(11) . . ? C6 C5 B1 108.77(11) . . ? C4 C5 B1 110.70(11) . . ? C6 C5 H5 108.6 . . ? C4 C5 H5 108.6 . . ? B1 C5 H5 108.6 . . ? C7 C6 C5 114.46(11) . . ? C7 C6 H6A 108.6 . . ? C5 C6 H6A 108.6 . . ? C7 C6 H6B 108.6 . . ? C5 C6 H6B 108.6 . . ? H6A C6 H6B 107.6 . . ? C8 C7 C6 114.40(11) . . ? C8 C7 H7A 108.7 . . ? C6 C7 H7A 108.7 . . ? C8 C7 H7B 108.7 . . ? C6 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C7 C8 C1 116.59(12) . . ? C7 C8 H8A 108.1 . . ? C1 C8 H8A 108.1 . . ? C7 C8 H8B 108.1 . . ? C1 C8 H8B 108.1 . . ? H8A C8 H8B 107.3 . . ? N1 C9 B1 176.11(13) . . ? N1 C10 C12 106.70(13) . . ? N1 C10 C13 106.87(12) . . ? C12 C10 C13 111.90(15) . . ? N1 C10 C11 107.31(13) . . ? C12 C10 C11 111.89(17) . . ? C13 C10 C11 111.79(15) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C22 C21 C26 112.70(12) . . ? C22 C21 B1 126.84(11) . . ? C26 C21 B1 120.45(12) . . ? F22 C22 C23 114.80(12) . . ? F22 C22 C21 121.12(12) . . ? C23 C22 C21 124.08(13) . . ? F23 C23 C24 119.61(13) . . ? F23 C23 C22 120.38(13) . . ? C24 C23 C22 119.99(13) . . ? F24 C24 C25 120.86(13) . . ? F24 C24 C23 120.55(14) . . ? C25 C24 C23 118.58(12) . . ? F25 C25 C24 119.68(12) . . ? F25 C25 C26 120.94(13) . . ? C24 C25 C26 119.38(13) . . ? F26 C26 C25 115.40(12) . . ? F26 C26 C21 119.49(12) . . ? C25 C26 C21 125.10(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 B1 C1 C2 -179.59(11) . . . . ? C5 B1 C1 C2 -64.53(13) . . . . ? C21 B1 C1 C2 67.09(14) . . . . ? C9 B1 C1 C8 -55.00(14) . . . . ? C5 B1 C1 C8 60.06(14) . . . . ? C21 B1 C1 C8 -168.32(11) . . . . ? C8 C1 C2 C3 -62.70(16) . . . . ? B1 C1 C2 C3 59.61(15) . . . . ? C1 C2 C3 C4 -45.28(18) . . . . ? C2 C3 C4 C5 39.02(19) . . . . ? C3 C4 C5 C6 73.28(16) . . . . ? C3 C4 C5 B1 -47.94(16) . . . . ? C9 B1 C5 C6 49.55(14) . . . . ? C1 B1 C5 C6 -63.85(13) . . . . ? C21 B1 C5 C6 168.49(11) . . . . ? C9 B1 C5 C4 172.34(11) . . . . ? C1 B1 C5 C4 58.94(14) . . . . ? C21 B1 C5 C4 -68.72(14) . . . . ? C4 C5 C6 C7 -64.39(16) . . . . ? B1 C5 C6 C7 57.94(15) . . . . ? C5 C6 C7 C8 -44.91(18) . . . . ? C6 C7 C8 C1 41.43(18) . . . . ? C2 C1 C8 C7 70.48(16) . . . . ? B1 C1 C8 C7 -50.65(16) . . . . ? C10 N1 C9 B1 26(4) . . . . ? C5 B1 C9 N1 -105(2) . . . . ? C1 B1 C9 N1 7(2) . . . . ? C21 B1 C9 N1 127(2) . . . . ? C9 N1 C10 C12 111(2) . . . . ? C9 N1 C10 C13 -9(2) . . . . ? C9 N1 C10 C11 -129(2) . . . . ? C9 B1 C21 C22 121.68(13) . . . . ? C5 B1 C21 C22 0.33(19) . . . . ? C1 B1 C21 C22 -123.55(14) . . . . ? C9 B1 C21 C26 -59.85(14) . . . . ? C5 B1 C21 C26 178.81(11) . . . . ? C1 B1 C21 C26 54.93(16) . . . . ? C26 C21 C22 F22 174.36(11) . . . . ? B1 C21 C22 F22 -7.06(19) . . . . ? C26 C21 C22 C23 -4.93(18) . . . . ? B1 C21 C22 C23 173.65(12) . . . . ? F22 C22 C23 F23 2.55(18) . . . . ? C21 C22 C23 F23 -178.12(12) . . . . ? F22 C22 C23 C24 -175.82(12) . . . . ? C21 C22 C23 C24 3.5(2) . . . . ? F23 C23 C24 F24 0.5(2) . . . . ? C22 C23 C24 F24 178.91(12) . . . . ? F23 C23 C24 C25 -177.93(12) . . . . ? C22 C23 C24 C25 0.4(2) . . . . ? F24 C24 C25 F25 -0.81(19) . . . . ? C23 C24 C25 F25 177.66(11) . . . . ? F24 C24 C25 C26 179.14(11) . . . . ? C23 C24 C25 C26 -2.4(2) . . . . ? F25 C25 C26 F26 -0.49(18) . . . . ? C24 C25 C26 F26 179.57(12) . . . . ? F25 C25 C26 C21 -179.39(12) . . . . ? C24 C25 C26 C21 0.7(2) . . . . ? C22 C21 C26 F26 -176.00(11) . . . . ? B1 C21 C26 F26 5.32(18) . . . . ? C22 C21 C26 C25 2.86(18) . . . . ? B1 C21 C26 C25 -175.82(12) . . . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 66.98 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.224 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.032 # Attachment '- 9.cif' data_erk6665 _database_code_depnum_ccdc_archive 'CCDC 894611' #TrackingRef '- 9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H40 B F5 N P' _chemical_formula_weight 623.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.4520(3) _cell_length_b 11.5100(2) _cell_length_c 16.6860(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.4080(10) _cell_angle_gamma 90.00 _cell_volume 3315.73(13) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 5709 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 1.188 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7718 _exptl_absorpt_correction_T_max 0.9430 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28006 _diffrn_reflns_av_R_equivalents 0.064 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.62 _diffrn_reflns_theta_max 66.92 _reflns_number_total 5714 _reflns_number_gt 4354 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _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^)+(0.0565P)^2^+1.8348P] 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 5714 _refine_ls_number_parameters 404 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0726 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1418 _refine_ls_wR_factor_gt 0.1277 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 P1 P 0.74629(4) 0.37408(6) 0.54972(4) 0.05511(19) Uani 1 1 d . . . B1 B 0.62427(16) 0.6948(3) 0.56018(16) 0.0535(7) Uani 1 1 d . . . C1 C 0.71693(14) 0.5126(2) 0.59238(15) 0.0587(6) Uani 1 1 d . . . H1A H 0.7014 0.4986 0.6457 0.070 Uiso 1 1 calc R . . H1B H 0.7608 0.5667 0.5993 0.070 Uiso 1 1 calc R . . C2 C 0.64885(14) 0.5660(2) 0.53517(14) 0.0549(6) Uani 1 1 d . . . H2A H 0.6039 0.5147 0.5335 0.066 Uiso 1 1 calc R . . H2B H 0.6627 0.5691 0.4804 0.066 Uiso 1 1 calc R . . C3 C 0.68398(14) 0.7959(2) 0.54632(15) 0.0583(6) Uani 1 1 d . . . H3 H 0.6783 0.8665 0.5730 0.070 Uiso 1 1 calc R . . C4 C 0.74074(15) 0.7909(2) 0.50113(16) 0.0638(7) Uani 1 1 d . . . H4 H 0.7531 0.7170 0.4826 0.077 Uiso 1 1 calc R . . C5 C 0.78706(17) 0.8914(3) 0.4767(2) 0.0768(8) Uani 1 1 d . . . H5A H 0.7848 0.9548 0.5155 0.092 Uiso 1 1 calc R . . H5B H 0.7629 0.9192 0.4235 0.092 Uiso 1 1 calc R . . C6 C 0.87102(17) 0.8638(3) 0.4726(2) 0.0782(8) Uani 1 1 d . . . H6A H 0.8738 0.7929 0.4406 0.094 Uiso 1 1 calc R . . H6B H 0.8937 0.9272 0.4447 0.094 Uiso 1 1 calc R . . C7 C 0.9178(2) 0.8471(3) 0.5549(2) 0.0972(11) Uani 1 1 d . . . H7A H 0.9182 0.9188 0.5855 0.146 Uiso 1 1 calc R . . H7B H 0.9704 0.8259 0.5489 0.146 Uiso 1 1 calc R . . H7C H 0.8948 0.7857 0.5834 0.146 Uiso 1 1 calc R . . C11 C 0.78151(13) 0.4330(2) 0.45881(14) 0.0548(6) Uani 1 1 d . . . C12 C 0.85012(14) 0.4987(2) 0.45987(15) 0.0582(6) Uani 1 1 d . . . C13 C 0.87066(16) 0.5377(3) 0.38689(17) 0.0668(7) Uani 1 1 d . . . H13 H 0.9162 0.5817 0.3881 0.080 Uiso 1 1 calc R . . C14 C 0.82696(18) 0.5142(3) 0.31295(17) 0.0725(8) Uani 1 1 d . . . C15 C 0.75995(18) 0.4511(3) 0.31280(16) 0.0741(8) Uani 1 1 d . . . H15 H 0.7289 0.4358 0.2630 0.089 Uiso 1 1 calc R . . C16 C 0.73634(15) 0.4091(3) 0.38371(15) 0.0622(7) Uani 1 1 d . . . C17 C 0.90363(15) 0.5277(3) 0.53635(17) 0.0700(7) Uani 1 1 d . . . H17A H 0.9338 0.4596 0.5550 0.105 Uiso 1 1 calc R . . H17B H 0.8734 0.5522 0.5777 0.105 Uiso 1 1 calc R . . H17C H 0.9382 0.5900 0.5257 0.105 Uiso 1 1 calc R . . C18 C 0.8519(2) 0.5563(4) 0.23513(19) 0.1024(12) Uani 1 1 d . . . H18A H 0.8361 0.5004 0.1924 0.154 Uiso 1 1 calc R . . H18B H 0.9078 0.5648 0.2426 0.154 Uiso 1 1 calc R . . H18C H 0.8278 0.6307 0.2204 0.154 Uiso 1 1 calc R . . C19 C 0.66270(17) 0.3386(3) 0.37566(18) 0.0849(9) Uani 1 1 d . . . H19A H 0.6386 0.3378 0.3195 0.127 Uiso 1 1 calc R . . H19B H 0.6274 0.3730 0.4088 0.127 Uiso 1 1 calc R . . H19C H 0.6747 0.2597 0.3936 0.127 Uiso 1 1 calc R . . C21 C 0.83371(14) 0.3133(2) 0.61157(15) 0.0570(6) Uani 1 1 d . . . C22 C 0.87839(15) 0.2348(2) 0.57243(16) 0.0627(7) Uani 1 1 d . . . C23 C 0.94334(17) 0.1821(3) 0.61597(19) 0.0726(8) Uani 1 1 d . . . H23 H 0.9733 0.1323 0.5884 0.087 Uiso 1 1 calc R . . C24 C 0.96553(17) 0.1999(3) 0.6979(2) 0.0760(8) Uani 1 1 d . . . C25 C 0.91907(17) 0.2714(3) 0.73610(18) 0.0752(8) Uani 1 1 d . . . H25 H 0.9320 0.2831 0.7922 0.090 Uiso 1 1 calc R . . C26 C 0.85401(16) 0.3272(3) 0.69603(16) 0.0647(7) Uani 1 1 d . . . C27 C 0.85800(18) 0.2003(3) 0.48450(17) 0.0768(8) Uani 1 1 d . . . H27A H 0.8748 0.2607 0.4504 0.115 Uiso 1 1 calc R . . H27B H 0.8024 0.1902 0.4716 0.115 Uiso 1 1 calc R . . H27C H 0.8838 0.1280 0.4751 0.115 Uiso 1 1 calc R . . C28 C 1.0352(2) 0.1393(4) 0.7434(2) 0.1066(12) Uani 1 1 d . . . H28A H 1.0332 0.0573 0.7299 0.160 Uiso 1 1 calc R . . H28B H 1.0353 0.1486 0.8012 0.160 Uiso 1 1 calc R . . H28C H 1.0821 0.1730 0.7284 0.160 Uiso 1 1 calc R . . C29 C 0.80590(19) 0.3963(3) 0.74748(16) 0.0875(10) Uani 1 1 d . . . H29A H 0.8094 0.4783 0.7350 0.131 Uiso 1 1 calc R . . H29B H 0.8252 0.3836 0.8043 0.131 Uiso 1 1 calc R . . H29C H 0.7523 0.3715 0.7361 0.131 Uiso 1 1 calc R . . C31 C 0.53878(14) 0.7390(2) 0.51409(15) 0.0548(6) Uani 1 1 d . . . F32 F 0.53557(9) 0.61291(15) 0.40073(9) 0.0774(5) Uani 1 1 d . . . C32 C 0.50319(15) 0.7005(2) 0.43934(16) 0.0600(6) Uani 1 1 d . . . F33 F 0.40665(11) 0.70370(17) 0.32401(11) 0.0965(6) Uani 1 1 d . . . C33 C 0.43615(17) 0.7468(3) 0.39685(16) 0.0706(8) Uani 1 1 d . . . F34 F 0.33485(10) 0.88256(17) 0.38952(12) 0.1000(6) Uani 1 1 d . . . C34 C 0.39994(16) 0.8365(3) 0.43018(19) 0.0730(8) Uani 1 1 d . . . F35 F 0.39582(11) 0.96409(16) 0.53836(12) 0.0976(6) Uani 1 1 d . . . C35 C 0.43123(16) 0.8773(3) 0.50375(18) 0.0692(7) Uani 1 1 d . . . F36 F 0.52732(10) 0.87962(15) 0.61534(10) 0.0795(5) Uani 1 1 d . . . C36 C 0.49883(15) 0.8302(2) 0.54357(16) 0.0612(6) Uani 1 1 d . . . N41 N 0.61643(12) 0.68710(18) 0.65647(12) 0.0557(5) Uani 1 1 d . . . C42 C 0.56345(16) 0.6164(3) 0.68048(16) 0.0659(7) Uani 1 1 d . . . H42 H 0.5280 0.5785 0.6412 0.079 Uiso 1 1 calc R . . C43 C 0.55956(19) 0.5975(3) 0.76169(19) 0.0815(9) Uani 1 1 d . . . H43 H 0.5226 0.5464 0.7777 0.098 Uiso 1 1 calc R . . C44 C 0.6113(2) 0.6553(3) 0.81895(19) 0.0865(10) Uani 1 1 d . . . H44 H 0.6100 0.6440 0.8745 0.104 Uiso 1 1 calc R . . C45 C 0.6640(2) 0.7290(3) 0.79368(18) 0.0908(10) Uani 1 1 d . . . H45 H 0.6989 0.7703 0.8316 0.109 Uiso 1 1 calc R . . C46 C 0.66548(18) 0.7419(3) 0.71288(16) 0.0747(8) Uani 1 1 d . . . H46 H 0.7027 0.7916 0.6960 0.090 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 P1 0.0527(3) 0.0606(4) 0.0513(4) 0.0005(3) 0.0049(3) 0.0010(3) B1 0.0528(15) 0.0615(18) 0.0458(15) 0.0019(13) 0.0053(12) 0.0006(13) C1 0.0559(14) 0.0673(16) 0.0522(14) 0.0038(12) 0.0063(11) 0.0045(12) C2 0.0527(13) 0.0627(16) 0.0488(13) 0.0007(11) 0.0053(10) 0.0001(11) C3 0.0553(14) 0.0621(16) 0.0562(14) 0.0012(12) 0.0040(11) 0.0012(12) C4 0.0624(15) 0.0631(16) 0.0655(16) 0.0075(13) 0.0078(13) -0.0019(13) C5 0.0724(18) 0.0736(19) 0.087(2) 0.0100(16) 0.0202(15) -0.0077(15) C6 0.0756(19) 0.074(2) 0.090(2) -0.0053(16) 0.0293(17) -0.0093(15) C7 0.086(2) 0.108(3) 0.098(3) -0.005(2) 0.0150(19) -0.008(2) C11 0.0501(13) 0.0612(15) 0.0526(14) -0.0036(11) 0.0055(11) 0.0041(12) C12 0.0541(14) 0.0617(16) 0.0596(15) -0.0007(12) 0.0109(11) 0.0068(12) C13 0.0625(15) 0.0706(18) 0.0709(18) 0.0080(14) 0.0213(14) 0.0090(13) C14 0.0749(18) 0.087(2) 0.0588(16) 0.0129(15) 0.0199(14) 0.0220(16) C15 0.0780(19) 0.095(2) 0.0473(15) -0.0022(14) 0.0024(13) 0.0168(17) C16 0.0581(14) 0.0760(18) 0.0511(14) -0.0043(13) 0.0035(11) 0.0059(13) C17 0.0556(15) 0.081(2) 0.0731(18) -0.0041(15) 0.0063(13) -0.0100(14) C18 0.111(3) 0.130(3) 0.072(2) 0.028(2) 0.0306(19) 0.028(2) C19 0.0713(18) 0.115(3) 0.0631(17) -0.0141(17) -0.0080(14) -0.0116(18) C21 0.0610(14) 0.0556(15) 0.0539(14) 0.0020(11) 0.0069(11) 0.0001(12) C22 0.0640(15) 0.0600(16) 0.0639(16) 0.0040(13) 0.0083(13) 0.0009(13) C23 0.0661(17) 0.0679(18) 0.083(2) 0.0052(15) 0.0069(15) 0.0105(14) C24 0.0683(17) 0.0730(19) 0.082(2) 0.0102(16) -0.0042(15) 0.0085(15) C25 0.0780(19) 0.080(2) 0.0617(17) 0.0063(15) -0.0093(14) 0.0046(16) C26 0.0668(16) 0.0705(17) 0.0550(15) 0.0030(13) 0.0023(12) 0.0024(14) C27 0.088(2) 0.0692(19) 0.0729(19) -0.0076(15) 0.0100(15) 0.0177(16) C28 0.088(2) 0.111(3) 0.110(3) 0.015(2) -0.019(2) 0.026(2) C29 0.097(2) 0.115(3) 0.0466(15) 0.0006(16) 0.0006(15) 0.026(2) C31 0.0519(13) 0.0581(15) 0.0537(14) 0.0047(12) 0.0047(11) -0.0032(11) F32 0.0812(10) 0.0832(11) 0.0622(9) -0.0126(8) -0.0077(8) 0.0051(9) C32 0.0598(15) 0.0592(16) 0.0593(15) 0.0012(12) 0.0034(12) -0.0028(12) F33 0.0952(12) 0.1050(14) 0.0771(11) 0.0029(10) -0.0280(9) -0.0040(11) C33 0.0676(17) 0.078(2) 0.0589(16) 0.0099(15) -0.0138(13) -0.0107(15) F34 0.0724(11) 0.0977(13) 0.1189(15) 0.0320(11) -0.0224(10) 0.0128(10) C34 0.0570(15) 0.0719(19) 0.085(2) 0.0198(16) -0.0045(14) 0.0039(14) F35 0.0882(12) 0.0862(13) 0.1175(15) 0.0047(11) 0.0125(11) 0.0340(10) C35 0.0639(16) 0.0640(17) 0.0786(19) 0.0083(15) 0.0068(14) 0.0099(14) F36 0.0849(11) 0.0792(11) 0.0709(10) -0.0118(8) 0.0003(8) 0.0211(9) C36 0.0591(15) 0.0608(16) 0.0624(16) 0.0033(13) 0.0040(12) 0.0026(13) N41 0.0574(12) 0.0593(13) 0.0504(11) -0.0005(10) 0.0078(9) 0.0041(10) C42 0.0656(16) 0.0730(18) 0.0610(16) 0.0043(14) 0.0155(13) 0.0014(14) C43 0.085(2) 0.092(2) 0.074(2) 0.0157(17) 0.0320(17) 0.0112(18) C44 0.107(3) 0.101(3) 0.0524(17) 0.0055(17) 0.0151(17) 0.020(2) C45 0.110(3) 0.106(3) 0.0534(17) -0.0045(17) -0.0008(17) -0.005(2) C46 0.0798(19) 0.086(2) 0.0552(16) -0.0042(15) 0.0002(14) -0.0093(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C11 1.847(3) . ? P1 C1 1.848(3) . ? P1 C21 1.850(3) . ? B1 C3 1.601(4) . ? B1 C2 1.615(4) . ? B1 N41 1.635(3) . ? B1 C31 1.656(4) . ? C1 C2 1.539(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 C4 1.331(3) . ? C3 H3 0.9400 . ? C4 C5 1.502(4) . ? C4 H4 0.9400 . ? C5 C6 1.511(4) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C6 C7 1.504(5) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 H7C 0.9700 . ? C11 C16 1.407(3) . ? C11 C12 1.414(3) . ? C12 C13 1.393(4) . ? C12 C17 1.504(4) . ? C13 C14 1.379(4) . ? C13 H13 0.9400 . ? C14 C15 1.376(4) . ? C14 C18 1.509(4) . ? C15 C16 1.395(4) . ? C15 H15 0.9400 . ? C16 C19 1.509(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 H17C 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 H18C 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 H19C 0.9700 . ? C21 C26 1.411(3) . ? C21 C22 1.414(4) . ? C22 C23 1.393(4) . ? C22 C27 1.511(4) . ? C23 C24 1.380(4) . ? C23 H23 0.9400 . ? C24 C25 1.376(4) . ? C24 C28 1.508(4) . ? C25 C26 1.388(4) . ? C25 H25 0.9400 . ? C26 C29 1.512(4) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 H28C 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? C31 C32 1.383(3) . ? C31 C36 1.390(4) . ? F32 C32 1.362(3) . ? C32 C33 1.383(4) . ? F33 C33 1.344(3) . ? C33 C34 1.370(4) . ? F34 C34 1.344(3) . ? C34 C35 1.353(4) . ? F35 C35 1.348(3) . ? C35 C36 1.378(4) . ? F36 C36 1.353(3) . ? N41 C46 1.334(3) . ? N41 C42 1.337(3) . ? C42 C43 1.384(4) . ? C42 H42 0.9400 . ? C43 C44 1.385(5) . ? C43 H43 0.9400 . ? C44 C45 1.363(5) . ? C44 H44 0.9400 . ? C45 C46 1.360(4) . ? C45 H45 0.9400 . ? C46 H46 0.9400 . ? 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 C11 P1 C1 98.27(12) . . ? C11 P1 C21 104.52(11) . . ? C1 P1 C21 111.33(11) . . ? C3 B1 C2 115.2(2) . . ? C3 B1 N41 109.3(2) . . ? C2 B1 N41 105.5(2) . . ? C3 B1 C31 105.7(2) . . ? C2 B1 C31 114.7(2) . . ? N41 B1 C31 105.89(19) . . ? C2 C1 P1 109.76(17) . . ? C2 C1 H1A 109.7 . . ? P1 C1 H1A 109.7 . . ? C2 C1 H1B 109.7 . . ? P1 C1 H1B 109.7 . . ? H1A C1 H1B 108.2 . . ? C1 C2 B1 114.6(2) . . ? C1 C2 H2A 108.6 . . ? B1 C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? B1 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? C4 C3 B1 127.2(3) . . ? C4 C3 H3 116.4 . . ? B1 C3 H3 116.4 . . ? C3 C4 C5 126.5(3) . . ? C3 C4 H4 116.7 . . ? C5 C4 H4 116.7 . . ? C4 C5 C6 114.5(3) . . ? C4 C5 H5A 108.6 . . ? C6 C5 H5A 108.6 . . ? C4 C5 H5B 108.6 . . ? C6 C5 H5B 108.6 . . ? H5A C5 H5B 107.6 . . ? C7 C6 C5 112.7(3) . . ? C7 C6 H6A 109.1 . . ? C5 C6 H6A 109.1 . . ? C7 C6 H6B 109.1 . . ? C5 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C16 C11 C12 118.6(2) . . ? C16 C11 P1 116.71(19) . . ? C12 C11 P1 124.67(18) . . ? C13 C12 C11 119.1(2) . . ? C13 C12 C17 117.6(2) . . ? C11 C12 C17 123.3(2) . . ? C14 C13 C12 122.7(3) . . ? C14 C13 H13 118.7 . . ? C12 C13 H13 118.7 . . ? C15 C14 C13 117.6(3) . . ? C15 C14 C18 121.3(3) . . ? C13 C14 C18 121.1(3) . . ? C14 C15 C16 122.5(3) . . ? C14 C15 H15 118.7 . . ? C16 C15 H15 118.7 . . ? C15 C16 C11 119.4(3) . . ? C15 C16 C19 117.7(2) . . ? C11 C16 C19 122.9(2) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C26 C21 C22 117.3(2) . . ? C26 C21 P1 125.5(2) . . ? C22 C21 P1 116.72(19) . . ? C23 C22 C21 119.9(3) . . ? C23 C22 C27 116.8(3) . . ? C21 C22 C27 123.3(2) . . ? C24 C23 C22 122.7(3) . . ? C24 C23 H23 118.6 . . ? C22 C23 H23 118.6 . . ? C25 C24 C23 116.7(3) . . ? C25 C24 C28 122.0(3) . . ? C23 C24 C28 121.2(3) . . ? C24 C25 C26 123.3(3) . . ? C24 C25 H25 118.3 . . ? C26 C25 H25 118.3 . . ? C25 C26 C21 119.8(3) . . ? C25 C26 C29 116.9(2) . . ? C21 C26 C29 123.2(2) . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C24 C28 H28A 109.5 . . ? C24 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C24 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C32 C31 C36 112.3(2) . . ? C32 C31 B1 125.2(2) . . ? C36 C31 B1 122.2(2) . . ? F32 C32 C31 120.1(2) . . ? F32 C32 C33 114.9(2) . . ? C31 C32 C33 125.0(3) . . ? F33 C33 C34 120.5(3) . . ? F33 C33 C32 120.3(3) . . ? C34 C33 C32 119.2(3) . . ? F34 C34 C35 121.4(3) . . ? F34 C34 C33 119.9(3) . . ? C35 C34 C33 118.8(3) . . ? F35 C35 C34 119.8(3) . . ? F35 C35 C36 119.9(3) . . ? C34 C35 C36 120.3(3) . . ? F36 C36 C35 116.1(2) . . ? F36 C36 C31 119.5(2) . . ? C35 C36 C31 124.4(3) . . ? C46 N41 C42 118.5(2) . . ? C46 N41 B1 122.0(2) . . ? C42 N41 B1 119.2(2) . . ? N41 C42 C43 121.6(3) . . ? N41 C42 H42 119.2 . . ? C43 C42 H42 119.2 . . ? C42 C43 C44 118.7(3) . . ? C42 C43 H43 120.7 . . ? C44 C43 H43 120.7 . . ? C45 C44 C43 119.1(3) . . ? C45 C44 H44 120.4 . . ? C43 C44 H44 120.4 . . ? C46 C45 C44 119.1(3) . . ? C46 C45 H45 120.5 . . ? C44 C45 H45 120.5 . . ? N41 C46 C45 123.0(3) . . ? N41 C46 H46 118.5 . . ? C45 C46 H46 118.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 P1 C1 C2 65.56(18) . . . . ? C21 P1 C1 C2 174.76(16) . . . . ? P1 C1 C2 B1 -173.08(17) . . . . ? C3 B1 C2 C1 71.8(3) . . . . ? N41 B1 C2 C1 -49.0(3) . . . . ? C31 B1 C2 C1 -165.1(2) . . . . ? C2 B1 C3 C4 16.2(4) . . . . ? N41 B1 C3 C4 134.9(3) . . . . ? C31 B1 C3 C4 -111.5(3) . . . . ? B1 C3 C4 C5 168.4(3) . . . . ? C3 C4 C5 C6 144.5(3) . . . . ? C4 C5 C6 C7 -71.6(4) . . . . ? C1 P1 C11 C16 -109.6(2) . . . . ? C21 P1 C11 C16 135.8(2) . . . . ? C1 P1 C11 C12 70.9(2) . . . . ? C21 P1 C11 C12 -43.8(2) . . . . ? C16 C11 C12 C13 0.1(4) . . . . ? P1 C11 C12 C13 179.6(2) . . . . ? C16 C11 C12 C17 -178.9(2) . . . . ? P1 C11 C12 C17 0.7(4) . . . . ? C11 C12 C13 C14 -0.4(4) . . . . ? C17 C12 C13 C14 178.6(3) . . . . ? C12 C13 C14 C15 1.0(4) . . . . ? C12 C13 C14 C18 -179.0(3) . . . . ? C13 C14 C15 C16 -1.4(4) . . . . ? C18 C14 C15 C16 178.6(3) . . . . ? C14 C15 C16 C11 1.1(4) . . . . ? C14 C15 C16 C19 -178.6(3) . . . . ? C12 C11 C16 C15 -0.4(4) . . . . ? P1 C11 C16 C15 -179.9(2) . . . . ? C12 C11 C16 C19 179.2(3) . . . . ? P1 C11 C16 C19 -0.3(4) . . . . ? C11 P1 C21 C26 136.1(2) . . . . ? C1 P1 C21 C26 31.0(3) . . . . ? C11 P1 C21 C22 -52.3(2) . . . . ? C1 P1 C21 C22 -157.4(2) . . . . ? C26 C21 C22 C23 -5.2(4) . . . . ? P1 C21 C22 C23 -177.5(2) . . . . ? C26 C21 C22 C27 172.6(3) . . . . ? P1 C21 C22 C27 0.3(4) . . . . ? C21 C22 C23 C24 2.2(4) . . . . ? C27 C22 C23 C24 -175.7(3) . . . . ? C22 C23 C24 C25 1.4(5) . . . . ? C22 C23 C24 C28 178.6(3) . . . . ? C23 C24 C25 C26 -1.9(5) . . . . ? C28 C24 C25 C26 -179.1(3) . . . . ? C24 C25 C26 C21 -1.2(5) . . . . ? C24 C25 C26 C29 176.0(3) . . . . ? C22 C21 C26 C25 4.7(4) . . . . ? P1 C21 C26 C25 176.3(2) . . . . ? C22 C21 C26 C29 -172.3(3) . . . . ? P1 C21 C26 C29 -0.7(4) . . . . ? C3 B1 C31 C32 101.9(3) . . . . ? C2 B1 C31 C32 -26.2(3) . . . . ? N41 B1 C31 C32 -142.1(2) . . . . ? C3 B1 C31 C36 -70.5(3) . . . . ? C2 B1 C31 C36 161.4(2) . . . . ? N41 B1 C31 C36 45.4(3) . . . . ? C36 C31 C32 F32 178.6(2) . . . . ? B1 C31 C32 F32 5.5(4) . . . . ? C36 C31 C32 C33 0.9(4) . . . . ? B1 C31 C32 C33 -172.2(3) . . . . ? F32 C32 C33 F33 1.5(4) . . . . ? C31 C32 C33 F33 179.3(2) . . . . ? F32 C32 C33 C34 -179.0(2) . . . . ? C31 C32 C33 C34 -1.2(4) . . . . ? F33 C33 C34 F34 -0.6(4) . . . . ? C32 C33 C34 F34 179.9(3) . . . . ? F33 C33 C34 C35 179.8(3) . . . . ? C32 C33 C34 C35 0.3(4) . . . . ? F34 C34 C35 F35 1.6(4) . . . . ? C33 C34 C35 F35 -178.8(3) . . . . ? F34 C34 C35 C36 -178.7(3) . . . . ? C33 C34 C35 C36 0.9(4) . . . . ? F35 C35 C36 F36 -2.8(4) . . . . ? C34 C35 C36 F36 177.5(3) . . . . ? F35 C35 C36 C31 178.4(2) . . . . ? C34 C35 C36 C31 -1.2(4) . . . . ? C32 C31 C36 F36 -178.4(2) . . . . ? B1 C31 C36 F36 -5.1(4) . . . . ? C32 C31 C36 C35 0.3(4) . . . . ? B1 C31 C36 C35 173.7(3) . . . . ? C3 B1 N41 C46 -12.5(3) . . . . ? C2 B1 N41 C46 112.0(3) . . . . ? C31 B1 N41 C46 -126.0(3) . . . . ? C3 B1 N41 C42 173.2(2) . . . . ? C2 B1 N41 C42 -62.3(3) . . . . ? C31 B1 N41 C42 59.7(3) . . . . ? C46 N41 C42 C43 -1.2(4) . . . . ? B1 N41 C42 C43 173.3(2) . . . . ? N41 C42 C43 C44 1.1(4) . . . . ? C42 C43 C44 C45 0.2(5) . . . . ? C43 C44 C45 C46 -1.3(5) . . . . ? C42 N41 C46 C45 0.0(4) . . . . ? B1 N41 C46 C45 -174.4(3) . . . . ? C44 C45 C46 N41 1.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 66.92 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.156 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.036 # Attachment '- 13.cif' data_erk6580 _database_code_depnum_ccdc_archive 'CCDC 894612' #TrackingRef '- 13.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C51 H57 B F5 N P2' _chemical_formula_weight 851.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.848(2) _cell_length_b 13.014(3) _cell_length_c 19.466(4) _cell_angle_alpha 95.90(3) _cell_angle_beta 92.54(3) _cell_angle_gamma 110.50(3) _cell_volume 2550.9(9) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 7297 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.109 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 900 _exptl_absorpt_coefficient_mu 1.183 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8909 _exptl_absorpt_correction_T_max 0.9432 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29514 _diffrn_reflns_av_R_equivalents 0.114 _diffrn_reflns_av_sigmaI/netI 0.0746 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.06 _diffrn_reflns_theta_max 67.50 _reflns_number_total 8352 _reflns_number_gt 4806 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _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. An unidentified disordered solvent molecule was found in the asymmetrical unit and could not be satisfactorily refined. The program SQUEEZE was therefore used to remove mathematically the effect of the solvent. ; 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 -0.495 0.006 0.500 347 63 ' ' _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^)+(0.0879P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8352 _refine_ls_number_parameters 553 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1233 _refine_ls_R_factor_gt 0.0669 _refine_ls_wR_factor_ref 0.1763 _refine_ls_wR_factor_gt 0.1545 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 P1 P 0.64262(10) 0.52117(7) 0.14929(5) 0.0514(3) Uani 1 1 d . . . P2 P 0.01168(9) 0.10451(7) 0.21604(4) 0.0496(3) Uani 1 1 d . . . B1 B 0.3932(4) 0.3394(3) 0.29208(19) 0.0462(10) Uani 1 1 d . . . N1 N 0.4802(3) 0.2592(2) 0.29160(13) 0.0484(7) Uani 1 1 d . . . C1 C 0.5002(4) 0.4110(3) 0.17781(16) 0.0529(9) Uani 1 1 d . . . H1A H 0.4200 0.4014 0.1487 0.063 Uiso 1 1 calc R . . H1B H 0.5156 0.3409 0.1727 0.063 Uiso 1 1 calc R . . C2 C 0.4817(4) 0.4420(3) 0.25384(16) 0.0497(9) Uani 1 1 d . . . H2A H 0.4401 0.4980 0.2560 0.060 Uiso 1 1 calc R . . H2B H 0.5690 0.4757 0.2795 0.060 Uiso 1 1 calc R . . C3 C 0.2502(3) 0.2761(3) 0.25027(17) 0.0477(8) Uani 1 1 d . . . H3A H 0.2108 0.3317 0.2426 0.057 Uiso 1 1 calc R . . H3B H 0.2643 0.2449 0.2046 0.057 Uiso 1 1 calc R . . C4 C 0.1476(3) 0.1826(3) 0.28237(17) 0.0509(9) Uani 1 1 d . . . H4A H 0.1132 0.2140 0.3217 0.061 Uiso 1 1 calc R . . H4B H 0.1892 0.1332 0.2993 0.061 Uiso 1 1 calc R . . C11 C 0.7750(4) 0.4996(3) 0.20260(17) 0.0487(9) Uani 1 1 d . . . C12 C 0.8328(3) 0.5779(3) 0.26129(18) 0.0508(9) Uani 1 1 d . . . C13 C 0.9270(4) 0.5643(3) 0.30592(19) 0.0601(10) Uani 1 1 d . . . H13 H 0.9650 0.6179 0.3445 0.072 Uiso 1 1 calc R . . C14 C 0.9670(4) 0.4748(3) 0.2958(2) 0.0644(11) Uani 1 1 d . . . C15 C 0.9121(4) 0.3987(3) 0.23757(19) 0.0618(10) Uani 1 1 d . . . H15 H 0.9403 0.3384 0.2289 0.074 Uiso 1 1 calc R . . C16 C 0.8163(4) 0.4089(3) 0.19143(17) 0.0513(9) Uani 1 1 d . . . C17 C 0.7961(4) 0.6790(3) 0.2783(2) 0.0640(11) Uani 1 1 d . . . H17A H 0.8100 0.7213 0.2393 0.096 Uiso 1 1 calc R . . H17B H 0.8509 0.7244 0.3188 0.096 Uiso 1 1 calc R . . H17C H 0.7039 0.6561 0.2877 0.096 Uiso 1 1 calc R . . C18 C 1.0674(5) 0.4603(5) 0.3468(2) 0.1077(18) Uani 1 1 d . . . H18A H 1.0664 0.4996 0.3918 0.161 Uiso 1 1 calc R . . H18B H 1.1547 0.4898 0.3305 0.161 Uiso 1 1 calc R . . H18C H 1.0453 0.3823 0.3507 0.161 Uiso 1 1 calc R . . C19 C 0.7662(4) 0.3194(3) 0.13007(18) 0.0659(11) Uani 1 1 d . . . H19A H 0.8081 0.3471 0.0893 0.099 Uiso 1 1 calc R . . H19B H 0.6712 0.2984 0.1217 0.099 Uiso 1 1 calc R . . H19C H 0.7872 0.2555 0.1398 0.099 Uiso 1 1 calc R . . C21 C 0.6767(4) 0.4872(3) 0.05953(17) 0.0530(9) Uani 1 1 d . . . C22 C 0.7988(4) 0.5575(3) 0.0397(2) 0.0599(10) Uani 1 1 d . . . C23 C 0.8331(4) 0.5426(4) -0.0273(2) 0.0702(12) Uani 1 1 d . . . H23 H 0.9164 0.5880 -0.0386 0.084 Uiso 1 1 calc R . . C24 C 0.7502(5) 0.4639(4) -0.0782(2) 0.0684(11) Uani 1 1 d . . . C25 C 0.6297(4) 0.3986(3) -0.05933(19) 0.0622(10) Uani 1 1 d . . . H25 H 0.5710 0.3452 -0.0933 0.075 Uiso 1 1 calc R . . C26 C 0.5905(4) 0.4073(3) 0.00677(18) 0.0536(9) Uani 1 1 d . . . C27 C 0.8948(4) 0.6525(4) 0.0887(2) 0.0842(14) Uani 1 1 d . . . H27A H 0.8467 0.6921 0.1141 0.126 Uiso 1 1 calc R . . H27B H 0.9579 0.7024 0.0623 0.126 Uiso 1 1 calc R . . H27C H 0.9413 0.6239 0.1210 0.126 Uiso 1 1 calc R . . C28 C 0.7897(5) 0.4496(4) -0.1511(2) 0.0935(15) Uani 1 1 d . . . H28A H 0.7120 0.4265 -0.1837 0.140 Uiso 1 1 calc R . . H28B H 0.8303 0.3938 -0.1549 0.140 Uiso 1 1 calc R . . H28C H 0.8523 0.5193 -0.1613 0.140 Uiso 1 1 calc R . . C29 C 0.4548(4) 0.3299(3) 0.01912(18) 0.0654(11) Uani 1 1 d . . . H29A H 0.4097 0.2877 -0.0245 0.098 Uiso 1 1 calc R . . H29B H 0.4043 0.3725 0.0387 0.098 Uiso 1 1 calc R . . H29C H 0.4632 0.2798 0.0511 0.098 Uiso 1 1 calc R . . C31 C -0.1246(4) -0.0003(3) 0.25176(18) 0.0525(9) Uani 1 1 d . . . C32 C -0.1447(4) -0.0136(3) 0.32230(18) 0.0554(9) Uani 1 1 d . . . C33 C -0.2683(4) -0.0816(3) 0.3392(2) 0.0637(11) Uani 1 1 d . . . H33 H -0.2803 -0.0891 0.3862 0.076 Uiso 1 1 calc R . . C34 C -0.3726(4) -0.1376(3) 0.2916(2) 0.0651(11) Uani 1 1 d . . . C35 C -0.3502(4) -0.1276(3) 0.2226(2) 0.0640(10) Uani 1 1 d . . . H35 H -0.4186 -0.1683 0.1884 0.077 Uiso 1 1 calc R . . C36 C -0.2309(4) -0.0600(3) 0.20173(18) 0.0518(9) Uani 1 1 d . . . C37 C -0.0406(4) 0.0405(4) 0.38204(19) 0.0792(13) Uani 1 1 d . . . H37A H -0.0230 0.1195 0.3887 0.119 Uiso 1 1 calc R . . H37B H 0.0399 0.0277 0.3719 0.119 Uiso 1 1 calc R . . H37C H -0.0720 0.0093 0.4239 0.119 Uiso 1 1 calc R . . C38 C -0.5051(5) -0.2081(4) 0.3117(3) 0.0994(16) Uani 1 1 d . . . H38A H -0.4978 -0.2178 0.3602 0.149 Uiso 1 1 calc R . . H38B H -0.5346 -0.2798 0.2836 0.149 Uiso 1 1 calc R . . H38C H -0.5685 -0.1723 0.3041 0.149 Uiso 1 1 calc R . . C39 C -0.2215(4) -0.0526(4) 0.12580(19) 0.0739(12) Uani 1 1 d . . . H39A H -0.3067 -0.0948 0.1009 0.111 Uiso 1 1 calc R . . H39B H -0.1561 -0.0825 0.1096 0.111 Uiso 1 1 calc R . . H39C H -0.1955 0.0241 0.1177 0.111 Uiso 1 1 calc R . . C41 C 0.0983(3) 0.0287(3) 0.16378(17) 0.0495(9) Uani 1 1 d . . . C42 C 0.1352(4) 0.0644(3) 0.09911(17) 0.0564(10) Uani 1 1 d . . . C43 C 0.2119(4) 0.0178(4) 0.0604(2) 0.0736(12) Uani 1 1 d . . . H43 H 0.2377 0.0436 0.0180 0.088 Uiso 1 1 calc R . . C44 C 0.2517(5) -0.0647(4) 0.0816(2) 0.0749(12) Uani 1 1 d . . . C45 C 0.2130(4) -0.1001(3) 0.1444(2) 0.0671(11) Uani 1 1 d . . . H45 H 0.2373 -0.1572 0.1594 0.081 Uiso 1 1 calc R . . C46 C 0.1401(4) -0.0552(3) 0.18609(19) 0.0549(9) Uani 1 1 d . . . C47 C 0.0957(4) 0.1529(3) 0.06924(19) 0.0702(12) Uani 1 1 d . . . H47A H 0.0017 0.1361 0.0718 0.105 Uiso 1 1 calc R . . H47B H 0.1158 0.1546 0.0212 0.105 Uiso 1 1 calc R . . H47C H 0.1443 0.2243 0.0956 0.105 Uiso 1 1 calc R . . C48 C 0.3340(6) -0.1143(5) 0.0376(3) 0.119(2) Uani 1 1 d . . . H48A H 0.4224 -0.0920 0.0603 0.179 Uiso 1 1 calc R . . H48B H 0.3386 -0.0882 -0.0075 0.179 Uiso 1 1 calc R . . H48C H 0.2936 -0.1943 0.0319 0.179 Uiso 1 1 calc R . . C49 C 0.1116(4) -0.0974(3) 0.2552(2) 0.0720(12) Uani 1 1 d . . . H49A H 0.1728 -0.0454 0.2914 0.108 Uiso 1 1 calc R . . H49B H 0.1218 -0.1687 0.2541 0.108 Uiso 1 1 calc R . . H49C H 0.0218 -0.1053 0.2645 0.108 Uiso 1 1 calc R . . C51 C 0.3755(3) 0.3706(3) 0.37480(16) 0.0448(8) Uani 1 1 d . . . F52 F 0.3970(2) 0.55673(16) 0.36538(10) 0.0685(6) Uani 1 1 d . . . C52 C 0.3704(3) 0.4715(3) 0.40364(17) 0.0498(9) Uani 1 1 d . . . F53 F 0.3380(3) 0.59538(18) 0.49269(11) 0.0805(7) Uani 1 1 d . . . C53 C 0.3403(4) 0.4941(3) 0.46970(18) 0.0556(9) Uani 1 1 d . . . F54 F 0.2824(3) 0.4360(2) 0.57769(11) 0.0897(8) Uani 1 1 d . . . C54 C 0.3119(4) 0.4152(3) 0.51303(18) 0.0619(10) Uani 1 1 d . . . F55 F 0.2895(3) 0.2341(2) 0.53100(11) 0.0952(8) Uani 1 1 d . . . C55 C 0.3161(4) 0.3138(3) 0.48852(19) 0.0621(10) Uani 1 1 d . . . F56 F 0.3477(2) 0.19109(16) 0.40369(10) 0.0702(6) Uani 1 1 d . . . C56 C 0.3460(4) 0.2942(3) 0.42255(18) 0.0532(9) Uani 1 1 d . . . C61 C 0.5962(4) 0.2942(3) 0.33027(18) 0.0576(10) Uani 1 1 d . . . H61 H 0.6210 0.3612 0.3600 0.069 Uiso 1 1 calc R . . C62 C 0.6796(4) 0.2358(3) 0.3280(2) 0.0676(11) Uani 1 1 d . . . H62 H 0.7607 0.2631 0.3553 0.081 Uiso 1 1 calc R . . C63 C 0.6444(5) 0.1377(3) 0.2857(2) 0.0740(12) Uani 1 1 d . . . H63 H 0.7004 0.0966 0.2836 0.089 Uiso 1 1 calc R . . C64 C 0.5255(4) 0.1005(3) 0.2463(2) 0.0702(11) Uani 1 1 d . . . H64 H 0.4987 0.0328 0.2173 0.084 Uiso 1 1 calc R . . C65 C 0.4461(4) 0.1626(3) 0.24959(18) 0.0545(9) Uani 1 1 d . . . H65 H 0.3657 0.1371 0.2218 0.065 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 P1 0.0512(6) 0.0426(5) 0.0614(6) 0.0119(4) 0.0013(4) 0.0168(4) P2 0.0493(6) 0.0443(5) 0.0559(5) 0.0100(4) 0.0028(4) 0.0168(4) B1 0.051(3) 0.035(2) 0.055(2) 0.0049(17) 0.0000(19) 0.0201(19) N1 0.052(2) 0.0411(16) 0.0542(16) 0.0049(13) 0.0013(14) 0.0203(14) C1 0.057(2) 0.047(2) 0.053(2) 0.0071(16) 0.0009(17) 0.0168(18) C2 0.057(2) 0.0388(19) 0.055(2) 0.0069(15) 0.0018(17) 0.0195(17) C3 0.050(2) 0.0383(18) 0.058(2) 0.0070(15) 0.0038(17) 0.0193(16) C4 0.052(2) 0.050(2) 0.054(2) 0.0100(16) 0.0077(17) 0.0211(18) C11 0.052(2) 0.0373(18) 0.059(2) 0.0094(16) 0.0081(17) 0.0181(17) C12 0.045(2) 0.044(2) 0.062(2) 0.0068(17) 0.0051(18) 0.0152(17) C13 0.050(2) 0.064(2) 0.063(2) -0.0031(19) -0.0045(19) 0.021(2) C14 0.054(3) 0.076(3) 0.070(2) 0.005(2) -0.002(2) 0.034(2) C15 0.063(3) 0.066(2) 0.069(2) 0.009(2) 0.006(2) 0.039(2) C16 0.051(2) 0.049(2) 0.056(2) 0.0074(17) 0.0052(17) 0.0206(18) C17 0.064(3) 0.044(2) 0.081(3) 0.0011(19) -0.006(2) 0.0182(19) C18 0.096(4) 0.139(5) 0.107(4) -0.008(3) -0.032(3) 0.076(4) C19 0.082(3) 0.054(2) 0.068(2) 0.0030(19) 0.001(2) 0.034(2) C21 0.048(2) 0.053(2) 0.062(2) 0.0242(18) 0.0031(18) 0.0185(18) C22 0.051(3) 0.061(2) 0.070(2) 0.026(2) 0.009(2) 0.018(2) C23 0.051(3) 0.082(3) 0.082(3) 0.036(2) 0.013(2) 0.022(2) C24 0.071(3) 0.084(3) 0.066(3) 0.033(2) 0.017(2) 0.040(3) C25 0.067(3) 0.061(2) 0.060(2) 0.0108(19) 0.007(2) 0.023(2) C26 0.055(2) 0.050(2) 0.057(2) 0.0156(17) 0.0029(18) 0.0174(19) C27 0.061(3) 0.080(3) 0.095(3) 0.032(3) 0.002(2) -0.001(2) C28 0.101(4) 0.118(4) 0.081(3) 0.031(3) 0.029(3) 0.055(3) C29 0.067(3) 0.060(2) 0.058(2) 0.0093(18) -0.003(2) 0.009(2) C31 0.056(2) 0.045(2) 0.064(2) 0.0107(17) 0.0090(19) 0.0260(18) C32 0.057(3) 0.053(2) 0.065(2) 0.0192(18) 0.0119(19) 0.025(2) C33 0.076(3) 0.052(2) 0.077(3) 0.030(2) 0.024(2) 0.031(2) C34 0.059(3) 0.046(2) 0.100(3) 0.026(2) 0.024(2) 0.023(2) C35 0.056(3) 0.049(2) 0.087(3) 0.007(2) 0.006(2) 0.020(2) C36 0.047(2) 0.043(2) 0.065(2) 0.0092(17) 0.0040(19) 0.0153(18) C37 0.078(3) 0.098(3) 0.063(2) 0.026(2) 0.009(2) 0.028(3) C38 0.082(4) 0.074(3) 0.134(4) 0.036(3) 0.036(3) 0.009(3) C39 0.064(3) 0.072(3) 0.069(3) -0.001(2) -0.002(2) 0.007(2) C41 0.048(2) 0.0396(19) 0.056(2) 0.0059(16) 0.0016(17) 0.0099(16) C42 0.054(2) 0.059(2) 0.048(2) 0.0036(17) 0.0018(18) 0.0119(19) C43 0.076(3) 0.080(3) 0.058(2) 0.000(2) 0.009(2) 0.022(3) C44 0.080(3) 0.066(3) 0.075(3) -0.013(2) 0.013(2) 0.027(2) C45 0.066(3) 0.049(2) 0.083(3) 0.001(2) 0.007(2) 0.019(2) C46 0.049(2) 0.043(2) 0.068(2) 0.0054(17) 0.0091(19) 0.0108(18) C47 0.068(3) 0.073(3) 0.067(2) 0.024(2) 0.002(2) 0.017(2) C48 0.134(5) 0.133(5) 0.105(4) -0.005(3) 0.035(4) 0.069(4) C49 0.081(3) 0.057(2) 0.092(3) 0.029(2) 0.019(2) 0.035(2) C51 0.041(2) 0.0422(19) 0.0537(19) 0.0063(16) -0.0039(16) 0.0188(16) F52 0.0932(17) 0.0439(11) 0.0745(13) 0.0119(10) 0.0169(12) 0.0298(11) C52 0.050(2) 0.045(2) 0.056(2) 0.0120(17) 0.0037(17) 0.0180(17) F53 0.1034(19) 0.0666(15) 0.0759(14) -0.0076(11) 0.0116(13) 0.0397(14) C53 0.057(3) 0.054(2) 0.057(2) -0.0034(18) -0.0007(18) 0.0253(19) F54 0.112(2) 0.1018(18) 0.0574(13) 0.0023(12) 0.0198(13) 0.0415(16) C54 0.069(3) 0.075(3) 0.042(2) -0.0018(19) 0.0026(19) 0.029(2) F55 0.139(2) 0.0876(17) 0.0688(14) 0.0350(13) 0.0216(14) 0.0434(17) C55 0.072(3) 0.061(2) 0.053(2) 0.0179(19) 0.0054(19) 0.020(2) F56 0.1000(18) 0.0519(12) 0.0687(13) 0.0185(10) 0.0102(12) 0.0363(12) C56 0.063(3) 0.047(2) 0.054(2) 0.0056(17) 0.0008(18) 0.0273(19) C61 0.059(3) 0.054(2) 0.062(2) 0.0088(18) -0.0013(19) 0.023(2) C62 0.054(3) 0.067(3) 0.090(3) 0.024(2) -0.003(2) 0.029(2) C63 0.069(3) 0.058(3) 0.108(3) 0.013(2) 0.010(3) 0.038(2) C64 0.070(3) 0.052(2) 0.098(3) 0.004(2) 0.009(2) 0.034(2) C65 0.052(2) 0.047(2) 0.066(2) 0.0045(18) 0.0029(18) 0.0212(18) _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 P1 C21 1.843(4) . ? P1 C11 1.852(4) . ? P1 C1 1.854(4) . ? P2 C4 1.840(3) . ? P2 C31 1.845(4) . ? P2 C41 1.849(4) . ? B1 C3 1.614(5) . ? B1 C2 1.621(5) . ? B1 N1 1.634(5) . ? B1 C51 1.656(5) . ? N1 C61 1.342(4) . ? N1 C65 1.350(4) . ? C1 C2 1.534(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 C4 1.543(5) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C11 C16 1.403(5) . ? C11 C12 1.410(5) . ? C12 C13 1.382(5) . ? C12 C17 1.512(5) . ? C13 C14 1.378(5) . ? C13 H13 0.9400 . ? C14 C15 1.384(5) . ? C14 C18 1.514(5) . ? C15 C16 1.393(5) . ? C15 H15 0.9400 . ? C16 C19 1.513(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 H17C 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 H18C 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 H19C 0.9700 . ? C21 C22 1.418(5) . ? C21 C26 1.422(5) . ? C22 C23 1.385(5) . ? C22 C27 1.513(5) . ? C23 C24 1.381(6) . ? C23 H23 0.9400 . ? C24 C25 1.376(5) . ? C24 C28 1.513(6) . ? C25 C26 1.379(5) . ? C25 H25 0.9400 . ? C26 C29 1.511(5) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 H28C 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? C31 C36 1.414(5) . ? C31 C32 1.418(5) . ? C32 C33 1.399(5) . ? C32 C37 1.510(5) . ? C33 C34 1.365(5) . ? C33 H33 0.9400 . ? C34 C35 1.386(5) . ? C34 C38 1.504(6) . ? C35 C36 1.391(5) . ? C35 H35 0.9400 . ? C36 C39 1.497(5) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C37 H37C 0.9700 . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C38 H38C 0.9700 . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C39 H39C 0.9700 . ? C41 C42 1.412(5) . ? C41 C46 1.419(5) . ? C42 C43 1.394(6) . ? C42 C47 1.520(5) . ? C43 C44 1.382(6) . ? C43 H43 0.9400 . ? C44 C45 1.381(6) . ? C44 C48 1.518(6) . ? C45 C46 1.382(5) . ? C45 H45 0.9400 . ? C46 C49 1.509(5) . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C47 H47C 0.9700 . ? C48 H48A 0.9700 . ? C48 H48B 0.9700 . ? C48 H48C 0.9700 . ? C49 H49A 0.9700 . ? C49 H49B 0.9700 . ? C49 H49C 0.9700 . ? C51 C52 1.395(5) . ? C51 C56 1.395(4) . ? F52 C52 1.354(4) . ? C52 C53 1.369(5) . ? F53 C53 1.357(4) . ? C53 C54 1.357(5) . ? F54 C54 1.337(4) . ? C54 C55 1.373(5) . ? F55 C55 1.353(4) . ? C55 C56 1.359(5) . ? F56 C56 1.361(4) . ? C61 C62 1.371(5) . ? C61 H61 0.9400 . ? C62 C63 1.366(6) . ? C62 H62 0.9400 . ? C63 C64 1.372(6) . ? C63 H63 0.9400 . ? C64 C65 1.371(5) . ? C64 H64 0.9400 . ? C65 H65 0.9400 . ? 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 C21 P1 C11 103.70(16) . . ? C21 P1 C1 112.74(16) . . ? C11 P1 C1 97.80(15) . . ? C4 P2 C31 112.33(16) . . ? C4 P2 C41 98.55(16) . . ? C31 P2 C41 106.71(15) . . ? C3 B1 C2 111.3(3) . . ? C3 B1 N1 111.0(3) . . ? C2 B1 N1 103.5(3) . . ? C3 B1 C51 109.8(3) . . ? C2 B1 C51 115.4(3) . . ? N1 B1 C51 105.4(2) . . ? C61 N1 C65 117.9(3) . . ? C61 N1 B1 119.0(3) . . ? C65 N1 B1 122.9(3) . . ? C2 C1 P1 110.0(2) . . ? C2 C1 H1A 109.7 . . ? P1 C1 H1A 109.7 . . ? C2 C1 H1B 109.7 . . ? P1 C1 H1B 109.7 . . ? H1A C1 H1B 108.2 . . ? C1 C2 B1 114.7(3) . . ? C1 C2 H2A 108.6 . . ? B1 C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? B1 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? C4 C3 B1 118.6(3) . . ? C4 C3 H3A 107.7 . . ? B1 C3 H3A 107.7 . . ? C4 C3 H3B 107.7 . . ? B1 C3 H3B 107.7 . . ? H3A C3 H3B 107.1 . . ? C3 C4 P2 109.1(2) . . ? C3 C4 H4A 109.9 . . ? P2 C4 H4A 109.9 . . ? C3 C4 H4B 109.9 . . ? P2 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? C16 C11 C12 117.9(3) . . ? C16 C11 P1 125.3(3) . . ? C12 C11 P1 116.7(3) . . ? C13 C12 C11 120.2(3) . . ? C13 C12 C17 117.3(3) . . ? C11 C12 C17 122.5(3) . . ? C14 C13 C12 122.2(3) . . ? C14 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? C13 C14 C15 117.7(3) . . ? C13 C14 C18 121.0(4) . . ? C15 C14 C18 121.3(4) . . ? C14 C15 C16 122.0(4) . . ? C14 C15 H15 119.0 . . ? C16 C15 H15 119.0 . . ? C15 C16 C11 119.9(3) . . ? C15 C16 C19 115.8(3) . . ? C11 C16 C19 124.3(3) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C22 C21 C26 116.9(3) . . ? C22 C21 P1 114.9(3) . . ? C26 C21 P1 127.9(3) . . ? C23 C22 C21 120.2(4) . . ? C23 C22 C27 117.2(4) . . ? C21 C22 C27 122.6(4) . . ? C24 C23 C22 122.8(4) . . ? C24 C23 H23 118.6 . . ? C22 C23 H23 118.6 . . ? C25 C24 C23 116.8(4) . . ? C25 C24 C28 121.5(4) . . ? C23 C24 C28 121.7(4) . . ? C24 C25 C26 123.5(4) . . ? C24 C25 H25 118.3 . . ? C26 C25 H25 118.3 . . ? C25 C26 C21 119.9(3) . . ? C25 C26 C29 117.1(3) . . ? C21 C26 C29 123.1(3) . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C24 C28 H28A 109.5 . . ? C24 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C24 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C36 C31 C32 117.6(3) . . ? C36 C31 P2 113.1(3) . . ? C32 C31 P2 128.3(3) . . ? C33 C32 C31 119.0(3) . . ? C33 C32 C37 116.4(3) . . ? C31 C32 C37 124.6(3) . . ? C34 C33 C32 124.0(4) . . ? C34 C33 H33 118.0 . . ? C32 C33 H33 118.0 . . ? C33 C34 C35 116.5(4) . . ? C33 C34 C38 122.6(4) . . ? C35 C34 C38 121.0(4) . . ? C34 C35 C36 123.0(4) . . ? C34 C35 H35 118.5 . . ? C36 C35 H35 118.5 . . ? C35 C36 C31 119.9(3) . . ? C35 C36 C39 117.6(3) . . ? C31 C36 C39 122.4(3) . . ? C32 C37 H37A 109.5 . . ? C32 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C32 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C34 C38 H38A 109.5 . . ? C34 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C34 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C36 C39 H39A 109.5 . . ? C36 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C36 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C42 C41 C46 117.9(3) . . ? C42 C41 P2 116.8(3) . . ? C46 C41 P2 125.1(3) . . ? C43 C42 C41 119.4(4) . . ? C43 C42 C47 117.7(3) . . ? C41 C42 C47 122.9(4) . . ? C44 C43 C42 122.9(4) . . ? C44 C43 H43 118.6 . . ? C42 C43 H43 118.6 . . ? C45 C44 C43 117.1(4) . . ? C45 C44 C48 121.6(4) . . ? C43 C44 C48 121.3(4) . . ? C44 C45 C46 122.9(4) . . ? C44 C45 H45 118.5 . . ? C46 C45 H45 118.5 . . ? C45 C46 C41 119.8(3) . . ? C45 C46 C49 117.1(3) . . ? C41 C46 C49 123.0(3) . . ? C42 C47 H47A 109.5 . . ? C42 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C42 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C44 C48 H48A 109.5 . . ? C44 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C44 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C46 C49 H49A 109.5 . . ? C46 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C46 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C52 C51 C56 111.0(3) . . ? C52 C51 B1 124.6(3) . . ? C56 C51 B1 123.9(3) . . ? F52 C52 C53 114.9(3) . . ? F52 C52 C51 119.8(3) . . ? C53 C52 C51 125.3(3) . . ? F53 C53 C54 119.1(3) . . ? F53 C53 C52 120.6(3) . . ? C54 C53 C52 120.3(3) . . ? F54 C54 C53 121.0(4) . . ? F54 C54 C55 121.2(4) . . ? C53 C54 C55 117.8(3) . . ? F55 C55 C56 120.8(4) . . ? F55 C55 C54 118.9(3) . . ? C56 C55 C54 120.3(3) . . ? C55 C56 F56 115.4(3) . . ? C55 C56 C51 125.4(3) . . ? F56 C56 C51 119.2(3) . . ? N1 C61 C62 122.3(4) . . ? N1 C61 H61 118.9 . . ? C62 C61 H61 118.9 . . ? C63 C62 C61 119.6(4) . . ? C63 C62 H62 120.2 . . ? C61 C62 H62 120.2 . . ? C62 C63 C64 118.7(4) . . ? C62 C63 H63 120.7 . . ? C64 C63 H63 120.7 . . ? C65 C64 C63 119.6(4) . . ? C65 C64 H64 120.2 . . ? C63 C64 H64 120.2 . . ? N1 C65 C64 121.9(4) . . ? N1 C65 H65 119.1 . . ? C64 C65 H65 119.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 B1 N1 C61 -172.8(3) . . . . ? C2 B1 N1 C61 67.7(4) . . . . ? C51 B1 N1 C61 -53.9(4) . . . . ? C3 B1 N1 C65 12.8(4) . . . . ? C2 B1 N1 C65 -106.7(3) . . . . ? C51 B1 N1 C65 131.7(3) . . . . ? C21 P1 C1 C2 177.2(2) . . . . ? C11 P1 C1 C2 68.7(3) . . . . ? P1 C1 C2 B1 -161.7(2) . . . . ? C3 B1 C2 C1 -55.5(4) . . . . ? N1 B1 C2 C1 63.8(3) . . . . ? C51 B1 C2 C1 178.4(3) . . . . ? C2 B1 C3 C4 -174.6(3) . . . . ? N1 B1 C3 C4 70.7(4) . . . . ? C51 B1 C3 C4 -45.5(4) . . . . ? B1 C3 C4 P2 -166.7(3) . . . . ? C31 P2 C4 C3 -174.1(2) . . . . ? C41 P2 C4 C3 73.8(3) . . . . ? C21 P1 C11 C16 -44.6(3) . . . . ? C1 P1 C11 C16 71.2(3) . . . . ? C21 P1 C11 C12 139.3(3) . . . . ? C1 P1 C11 C12 -105.0(3) . . . . ? C16 C11 C12 C13 -0.1(5) . . . . ? P1 C11 C12 C13 176.4(3) . . . . ? C16 C11 C12 C17 179.8(3) . . . . ? P1 C11 C12 C17 -3.8(5) . . . . ? C11 C12 C13 C14 -0.7(6) . . . . ? C17 C12 C13 C14 179.4(4) . . . . ? C12 C13 C14 C15 1.7(6) . . . . ? C12 C13 C14 C18 -178.1(4) . . . . ? C13 C14 C15 C16 -2.1(6) . . . . ? C18 C14 C15 C16 177.8(4) . . . . ? C14 C15 C16 C11 1.4(6) . . . . ? C14 C15 C16 C19 179.8(4) . . . . ? C12 C11 C16 C15 -0.3(5) . . . . ? P1 C11 C16 C15 -176.4(3) . . . . ? C12 C11 C16 C19 -178.5(3) . . . . ? P1 C11 C16 C19 5.4(5) . . . . ? C11 P1 C21 C22 -63.6(3) . . . . ? C1 P1 C21 C22 -168.2(3) . . . . ? C11 P1 C21 C26 123.5(3) . . . . ? C1 P1 C21 C26 18.8(4) . . . . ? C26 C21 C22 C23 -3.9(5) . . . . ? P1 C21 C22 C23 -177.7(3) . . . . ? C26 C21 C22 C27 174.6(3) . . . . ? P1 C21 C22 C27 0.8(5) . . . . ? C21 C22 C23 C24 3.0(6) . . . . ? C27 C22 C23 C24 -175.5(4) . . . . ? C22 C23 C24 C25 -0.5(6) . . . . ? C22 C23 C24 C28 179.7(4) . . . . ? C23 C24 C25 C26 -1.0(6) . . . . ? C28 C24 C25 C26 178.8(4) . . . . ? C24 C25 C26 C21 0.0(6) . . . . ? C24 C25 C26 C29 179.7(4) . . . . ? C22 C21 C26 C25 2.4(5) . . . . ? P1 C21 C26 C25 175.3(3) . . . . ? C22 C21 C26 C29 -177.3(3) . . . . ? P1 C21 C26 C29 -4.4(5) . . . . ? C4 P2 C31 C36 179.0(2) . . . . ? C41 P2 C31 C36 -74.0(3) . . . . ? C4 P2 C31 C32 11.2(4) . . . . ? C41 P2 C31 C32 118.1(3) . . . . ? C36 C31 C32 C33 -1.9(5) . . . . ? P2 C31 C32 C33 165.5(3) . . . . ? C36 C31 C32 C37 177.8(4) . . . . ? P2 C31 C32 C37 -14.8(5) . . . . ? C31 C32 C33 C34 0.5(6) . . . . ? C37 C32 C33 C34 -179.2(4) . . . . ? C32 C33 C34 C35 2.1(6) . . . . ? C32 C33 C34 C38 -178.7(4) . . . . ? C33 C34 C35 C36 -3.3(6) . . . . ? C38 C34 C35 C36 177.4(4) . . . . ? C34 C35 C36 C31 2.0(6) . . . . ? C34 C35 C36 C39 -177.3(4) . . . . ? C32 C31 C36 C35 0.7(5) . . . . ? P2 C31 C36 C35 -168.6(3) . . . . ? C32 C31 C36 C39 180.0(3) . . . . ? P2 C31 C36 C39 10.7(4) . . . . ? C4 P2 C41 C42 -106.3(3) . . . . ? C31 P2 C41 C42 137.2(3) . . . . ? C4 P2 C41 C46 68.0(3) . . . . ? C31 P2 C41 C46 -48.5(3) . . . . ? C46 C41 C42 C43 -0.9(5) . . . . ? P2 C41 C42 C43 173.8(3) . . . . ? C46 C41 C42 C47 179.5(3) . . . . ? P2 C41 C42 C47 -5.8(4) . . . . ? C41 C42 C43 C44 1.6(6) . . . . ? C47 C42 C43 C44 -178.7(4) . . . . ? C42 C43 C44 C45 -0.5(6) . . . . ? C42 C43 C44 C48 179.3(4) . . . . ? C43 C44 C45 C46 -1.3(6) . . . . ? C48 C44 C45 C46 178.8(4) . . . . ? C44 C45 C46 C41 2.0(6) . . . . ? C44 C45 C46 C49 -176.5(4) . . . . ? C42 C41 C46 C45 -0.8(5) . . . . ? P2 C41 C46 C45 -175.1(3) . . . . ? C42 C41 C46 C49 177.6(3) . . . . ? P2 C41 C46 C49 3.4(5) . . . . ? C3 B1 C51 C52 -94.2(4) . . . . ? C2 B1 C51 C52 32.6(5) . . . . ? N1 B1 C51 C52 146.1(3) . . . . ? C3 B1 C51 C56 76.8(4) . . . . ? C2 B1 C51 C56 -156.4(3) . . . . ? N1 B1 C51 C56 -42.9(4) . . . . ? C56 C51 C52 F52 179.6(3) . . . . ? B1 C51 C52 F52 -8.4(5) . . . . ? C56 C51 C52 C53 -0.2(5) . . . . ? B1 C51 C52 C53 171.8(3) . . . . ? F52 C52 C53 F53 0.2(5) . . . . ? C51 C52 C53 F53 -180.0(3) . . . . ? F52 C52 C53 C54 -179.9(3) . . . . ? C51 C52 C53 C54 -0.1(6) . . . . ? F53 C53 C54 F54 -0.2(6) . . . . ? C52 C53 C54 F54 180.0(3) . . . . ? F53 C53 C54 C55 -179.4(3) . . . . ? C52 C53 C54 C55 0.7(6) . . . . ? F54 C54 C55 F55 0.1(6) . . . . ? C53 C54 C55 F55 179.4(4) . . . . ? F54 C54 C55 C56 179.8(4) . . . . ? C53 C54 C55 C56 -0.9(6) . . . . ? F55 C55 C56 F56 -0.4(5) . . . . ? C54 C55 C56 F56 179.9(3) . . . . ? F55 C55 C56 C51 -179.7(3) . . . . ? C54 C55 C56 C51 0.6(6) . . . . ? C52 C51 C56 C55 0.0(5) . . . . ? B1 C51 C56 C55 -172.1(4) . . . . ? C52 C51 C56 F56 -179.2(3) . . . . ? B1 C51 C56 F56 8.7(5) . . . . ? C65 N1 C61 C62 0.4(5) . . . . ? B1 N1 C61 C62 -174.3(3) . . . . ? N1 C61 C62 C63 -0.8(6) . . . . ? C61 C62 C63 C64 0.2(6) . . . . ? C62 C63 C64 C65 0.8(6) . . . . ? C61 N1 C65 C64 0.6(5) . . . . ? B1 N1 C65 C64 175.1(3) . . . . ? C63 C64 C65 N1 -1.2(6) . . . . ? _diffrn_measured_fraction_theta_max 0.908 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.908 _refine_diff_density_max 0.277 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.053 # Attachment '- 16 sad1.cif' data_sad1 _database_code_depnum_ccdc_archive 'CCDC 894613' #TrackingRef '- 16 sad1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H46 Al B N2 Si' _chemical_formula_weight 404.49 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' Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.2424(5) _cell_length_b 10.8886(6) _cell_length_c 13.5329(6) _cell_angle_alpha 70.176(4) _cell_angle_beta 88.676(4) _cell_angle_gamma 68.055(4) _cell_volume 1307.62(11) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 13403 _cell_measurement_theta_min 1.61 _cell_measurement_theta_max 28.32 _exptl_crystal_description Plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.027 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.133 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9651 _exptl_absorpt_correction_T_max 0.9882 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'imaging plate detector system' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10412 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0542 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 27.95 _reflns_number_total 6227 _reflns_number_gt 4403 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT+' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0487P)^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 6227 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0895 _refine_ls_wR_factor_gt 0.0840 _refine_ls_goodness_of_fit_ref 0.909 _refine_ls_restrained_S_all 0.909 _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 Al1 Al 0.87387(4) 0.89176(4) 0.30463(3) 0.02251(10) Uani 1 1 d . . . H1 H 0.9115(15) 0.7255(15) 0.2842(12) 0.027(4) Uiso 1 1 d . . . H2 H 0.7937(16) 0.9051(16) 0.1899(12) 0.030(4) Uiso 1 1 d . . . C11 C 1.06044(14) 0.90513(14) 0.30487(11) 0.0263(3) Uani 1 1 d . . . C12 C 1.00042(15) 1.04586(15) 0.26303(12) 0.0290(3) Uani 1 1 d . . . H12 H 1.0539 1.1045 0.2511 0.035 Uiso 1 1 calc R . . N1 N 0.84472(12) 1.10481(11) 0.23632(9) 0.0249(2) Uani 1 1 d . . . C13 C 0.80366(15) 1.17891(14) 0.12035(11) 0.0289(3) Uani 1 1 d . . . H13A H 0.8473 1.1137 0.0847 0.035 Uiso 1 1 calc R . . H13B H 0.8368 1.2545 0.0958 0.035 Uiso 1 1 calc R . . C14 C 0.64511(15) 1.23809(14) 0.09461(12) 0.0303(3) Uani 1 1 d . . . H14A H 0.6203 1.2841 0.0194 0.036 Uiso 1 1 calc R . . H14B H 0.6121 1.1623 0.1178 0.036 Uiso 1 1 calc R . . N2 N 0.57674(12) 1.33961(12) 0.14656(10) 0.0307(3) Uani 1 1 d . . . C201 C 0.42347(16) 1.40161(17) 0.11918(14) 0.0407(4) Uani 1 1 d . . . H20A H 0.3869 1.3286 0.1441 0.049 Uiso 1 1 calc R . . H20B H 0.4012 1.4462 0.0438 0.049 Uiso 1 1 calc R . . H20C H 0.3813 1.4709 0.1516 0.049 Uiso 1 1 calc R . . C15 C 0.61344(15) 1.26836(15) 0.26049(12) 0.0312(3) Uani 1 1 d . . . H15A H 0.5781 1.1943 0.2844 0.037 Uiso 1 1 calc R . . H15B H 0.5691 1.3349 0.2949 0.037 Uiso 1 1 calc R . . C16 C 0.77200(15) 1.20571(14) 0.29054(12) 0.0291(3) Uani 1 1 d . . . H16A H 0.8065 1.2804 0.2714 0.035 Uiso 1 1 calc R . . H16B H 0.7932 1.1573 0.3657 0.035 Uiso 1 1 calc R . . C111 C 0.75480(15) 0.87398(14) 0.41970(12) 0.0308(3) Uani 1 1 d . . . H11A H 0.7682 0.9255 0.4611 0.037 Uiso 1 1 calc R . . H11B H 0.6576 0.9198 0.3888 0.037 Uiso 1 1 calc R . . C112 C 0.77860(18) 0.72475(16) 0.49469(13) 0.0393(4) Uani 1 1 d . . . H112 H 0.7678 0.6731 0.4525 0.047 Uiso 1 1 calc R . . C113 C 0.6711(2) 0.7232(2) 0.57381(15) 0.0526(5) Uani 1 1 d . . . H11C H 0.6881 0.6270 0.6168 0.063 Uiso 1 1 calc R . . H11D H 0.5772 0.7685 0.5366 0.063 Uiso 1 1 calc R . . H11E H 0.6802 0.7730 0.6180 0.063 Uiso 1 1 calc R . . C114 C 0.9258(2) 0.6488(3) 0.55132(19) 0.0800(8) Uani 1 1 d . . . H11F H 0.9414 0.7001 0.5921 0.096 Uiso 1 1 calc R . . H11G H 0.9929 0.6422 0.5007 0.096 Uiso 1 1 calc R . . H11H H 0.9378 0.5553 0.5976 0.096 Uiso 1 1 calc R . . B1 B 0.84484(17) 0.78005(15) 0.19894(13) 0.0259(3) Uani 1 1 d . . . C01 C 0.94186(15) 0.75655(16) 0.10751(12) 0.0316(3) Uani 1 1 d . . . H01 H 1.0160 0.7895 0.1107 0.038 Uiso 1 1 calc R . . C02 C 0.84954(18) 0.8451(2) 0.00034(13) 0.0432(4) Uani 1 1 d . . . H02A H 0.8257 0.9435 -0.0118 0.052 Uiso 1 1 calc R . . H02B H 0.9047 0.8232 -0.0542 0.052 Uiso 1 1 calc R . . C03 C 0.71251(18) 0.8229(2) -0.00995(13) 0.0456(4) Uani 1 1 d . . . H03A H 0.6526 0.8976 -0.0714 0.055 Uiso 1 1 calc R . . H03B H 0.7353 0.7352 -0.0214 0.055 Uiso 1 1 calc R . . C04 C 0.62959(16) 0.81928(18) 0.08527(13) 0.0382(3) Uani 1 1 d . . . H04A H 0.5582 0.7843 0.0787 0.046 Uiso 1 1 calc R . . H04B H 0.5820 0.9145 0.0839 0.046 Uiso 1 1 calc R . . C05 C 0.71966(14) 0.72790(14) 0.19269(11) 0.0278(3) Uani 1 1 d . . . H05 H 0.6615 0.7422 0.2477 0.033 Uiso 1 1 calc R . . C06 C 0.78542(17) 0.56857(15) 0.21114(14) 0.0376(4) Uani 1 1 d . . . H06A H 0.8226 0.5177 0.2844 0.045 Uiso 1 1 calc R . . H06B H 0.7114 0.5404 0.1974 0.045 Uiso 1 1 calc R . . C07 C 0.90374(18) 0.52346(17) 0.14402(16) 0.0454(4) Uani 1 1 d . . . H07A H 0.8611 0.5420 0.0753 0.054 Uiso 1 1 calc R . . H07B H 0.9557 0.4230 0.1759 0.054 Uiso 1 1 calc R . . C08 C 1.00891(16) 0.59639(17) 0.12990(14) 0.0395(4) Uani 1 1 d . . . H08A H 1.0615 0.5809 0.0726 0.047 Uiso 1 1 calc R . . H08B H 1.0751 0.5518 0.1929 0.047 Uiso 1 1 calc R . . Si1 Si 1.25485(4) 0.80432(4) 0.33570(3) 0.03098(10) Uani 1 1 d . . . C101 C 1.29737(19) 0.66315(19) 0.46949(14) 0.0492(4) Uani 1 1 d . . . H10A H 1.2532 0.7043 0.5203 0.059 Uiso 1 1 calc R . . H10B H 1.3982 0.6195 0.4886 0.059 Uiso 1 1 calc R . . H10C H 1.2626 0.5930 0.4684 0.059 Uiso 1 1 calc R . . C102 C 1.34740(19) 0.9246(2) 0.33062(17) 0.0506(4) Uani 1 1 d . . . H10D H 1.3204 1.0006 0.2632 0.061 Uiso 1 1 calc R . . H10E H 1.4481 0.8723 0.3402 0.061 Uiso 1 1 calc R . . H10F H 1.3214 0.9628 0.3858 0.061 Uiso 1 1 calc R . . C103 C 1.31683(17) 0.7189(2) 0.23560(15) 0.0469(4) Uani 1 1 d . . . H10G H 1.2643 0.6624 0.2344 0.056 Uiso 1 1 calc R . . H10H H 1.4159 0.6595 0.2538 0.056 Uiso 1 1 calc R . . H10I H 1.3022 0.7906 0.1670 0.056 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 Al1 0.0257(2) 0.02206(19) 0.0213(2) -0.00812(15) 0.00428(15) -0.01070(15) C11 0.0260(7) 0.0314(7) 0.0250(7) -0.0137(6) 0.0055(5) -0.0117(5) C12 0.0281(7) 0.0318(7) 0.0335(8) -0.0142(6) 0.0080(6) -0.0165(6) N1 0.0275(6) 0.0220(5) 0.0267(6) -0.0101(5) 0.0059(5) -0.0103(4) C13 0.0364(8) 0.0253(6) 0.0255(7) -0.0082(6) 0.0094(6) -0.0134(6) C14 0.0379(8) 0.0251(6) 0.0273(7) -0.0089(6) 0.0033(6) -0.0122(6) N2 0.0319(6) 0.0246(6) 0.0337(7) -0.0113(5) 0.0028(5) -0.0084(5) C201 0.0355(8) 0.0349(8) 0.0479(10) -0.0164(7) 0.0014(7) -0.0080(6) C15 0.0345(7) 0.0271(7) 0.0339(8) -0.0148(6) 0.0095(6) -0.0109(6) C16 0.0371(8) 0.0236(6) 0.0301(7) -0.0131(6) 0.0060(6) -0.0125(6) C111 0.0326(7) 0.0292(7) 0.0315(8) -0.0099(6) 0.0088(6) -0.0141(6) C112 0.0490(9) 0.0350(8) 0.0290(8) -0.0060(6) 0.0117(7) -0.0164(7) C113 0.0600(12) 0.0557(11) 0.0396(10) -0.0058(8) 0.0196(9) -0.0307(9) C114 0.0575(13) 0.0755(15) 0.0524(13) 0.0190(11) 0.0061(11) -0.0050(11) B1 0.0319(8) 0.0219(7) 0.0248(8) -0.0086(6) 0.0009(6) -0.0110(6) C01 0.0310(7) 0.0409(8) 0.0296(8) -0.0128(6) 0.0066(6) -0.0209(6) C02 0.0464(9) 0.0583(10) 0.0258(8) -0.0111(7) 0.0076(7) -0.0250(8) C03 0.0425(9) 0.0613(11) 0.0297(9) -0.0139(8) -0.0031(7) -0.0182(8) C04 0.0303(8) 0.0462(9) 0.0376(9) -0.0131(7) -0.0008(6) -0.0157(7) C05 0.0275(7) 0.0280(7) 0.0295(7) -0.0110(6) 0.0068(6) -0.0118(5) C06 0.0389(8) 0.0295(7) 0.0494(10) -0.0136(7) 0.0044(7) -0.0193(6) C07 0.0460(9) 0.0353(8) 0.0625(12) -0.0296(8) 0.0070(8) -0.0132(7) C08 0.0323(8) 0.0470(9) 0.0416(9) -0.0242(8) 0.0100(7) -0.0108(7) Si1 0.02451(19) 0.0365(2) 0.0357(2) -0.01897(18) 0.00402(16) -0.01042(16) C101 0.0438(10) 0.0473(10) 0.0440(10) -0.0141(8) -0.0035(8) -0.0060(8) C102 0.0363(9) 0.0612(11) 0.0666(13) -0.0315(10) 0.0048(8) -0.0241(8) C103 0.0351(9) 0.0602(11) 0.0550(11) -0.0371(9) 0.0120(8) -0.0144(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 Al1 C111 1.9581(15) . ? Al1 C11 1.9700(14) . ? Al1 N1 2.0894(11) . ? Al1 B1 2.2547(15) . ? Al1 C12 2.4007(14) . ? Al1 H1 1.821(14) . ? Al1 H2 1.710(15) . ? C11 C12 1.3304(19) . ? C11 Si1 1.8542(14) . ? C12 N1 1.4799(17) . ? C12 H12 0.9600 . ? N1 C13 1.4863(18) . ? N1 C16 1.4867(16) . ? C13 C14 1.505(2) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C14 N2 1.4602(17) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? N2 C15 1.4553(19) . ? N2 C201 1.4568(19) . ? C201 H20A 0.9599 . ? C201 H20B 0.9599 . ? C201 H20C 0.9599 . ? C15 C16 1.511(2) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C111 C112 1.525(2) . ? C111 H11A 0.9600 . ? C111 H11B 0.9600 . ? C112 C114 1.496(3) . ? C112 C113 1.518(2) . ? C112 H112 0.9600 . ? C113 H11C 0.9599 . ? C113 H11D 0.9599 . ? C113 H11E 0.9599 . ? C114 H11F 0.9599 . ? C114 H11G 0.9599 . ? C114 H11H 0.9599 . ? B1 C01 1.597(2) . ? B1 C05 1.598(2) . ? B1 H1 1.191(15) . ? B1 H2 1.224(15) . ? C01 C08 1.537(2) . ? C01 C02 1.537(2) . ? C01 H01 0.9600 . ? C02 C03 1.528(2) . ? C02 H02A 0.9600 . ? C02 H02B 0.9600 . ? C03 C04 1.524(2) . ? C03 H03A 0.9600 . ? C03 H03B 0.9600 . ? C04 C05 1.533(2) . ? C04 H04A 0.9600 . ? C04 H04B 0.9600 . ? C05 C06 1.5383(19) . ? C05 H05 0.9600 . ? C06 C07 1.530(2) . ? C06 H06A 0.9600 . ? C06 H06B 0.9600 . ? C07 C08 1.534(2) . ? C07 H07A 0.9600 . ? C07 H07B 0.9600 . ? C08 H08A 0.9600 . ? C08 H08B 0.9600 . ? Si1 C103 1.8648(16) . ? Si1 C101 1.8652(19) . ? Si1 C102 1.8664(18) . ? C101 H10A 0.9599 . ? C101 H10B 0.9599 . ? C101 H10C 0.9599 . ? C102 H10D 0.9599 . ? C102 H10E 0.9599 . ? C102 H10F 0.9599 . ? C103 H10G 0.9599 . ? C103 H10H 0.9599 . ? C103 H10I 0.9599 . ? 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 C111 Al1 C11 128.72(6) . . ? C111 Al1 N1 107.93(5) . . ? C11 Al1 N1 71.29(5) . . ? C111 Al1 B1 110.86(6) . . ? C11 Al1 B1 113.48(6) . . ? N1 Al1 B1 118.67(5) . . ? C111 Al1 C12 124.40(6) . . ? C11 Al1 C12 33.65(5) . . ? N1 Al1 C12 37.69(4) . . ? B1 Al1 C12 123.88(6) . . ? C111 Al1 H1 100.8(5) . . ? C11 Al1 H1 103.3(5) . . ? N1 Al1 H1 146.7(5) . . ? B1 Al1 H1 31.8(5) . . ? C12 Al1 H1 130.6(5) . . ? C111 Al1 H2 112.1(5) . . ? C11 Al1 H2 119.1(5) . . ? N1 Al1 H2 89.2(5) . . ? B1 Al1 H2 32.4(5) . . ? C12 Al1 H2 109.0(5) . . ? H1 Al1 H2 64.1(7) . . ? C12 C11 Si1 123.30(11) . . ? C12 C11 Al1 91.23(9) . . ? Si1 C11 Al1 145.46(8) . . ? C11 C12 N1 114.70(12) . . ? C11 C12 Al1 55.13(8) . . ? N1 C12 Al1 59.67(6) . . ? C11 C12 H12 122.6 . . ? N1 C12 H12 122.6 . . ? Al1 C12 H12 176.2 . . ? C12 N1 C13 111.19(11) . . ? C12 N1 C16 111.29(10) . . ? C13 N1 C16 108.83(10) . . ? C12 N1 Al1 82.64(7) . . ? C13 N1 Al1 119.42(8) . . ? C16 N1 Al1 120.32(9) . . ? N1 C13 C14 110.48(11) . . ? N1 C13 H13A 109.6 . . ? C14 C13 H13A 109.6 . . ? N1 C13 H13B 109.6 . . ? C14 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? N2 C14 C13 110.44(11) . . ? N2 C14 H14A 109.6 . . ? C13 C14 H14A 109.6 . . ? N2 C14 H14B 109.6 . . ? C13 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? C15 N2 C201 110.54(12) . . ? C15 N2 C14 109.10(10) . . ? C201 N2 C14 111.01(12) . . ? N2 C201 H20A 109.5 . . ? N2 C201 H20B 109.5 . . ? H20A C201 H20B 109.5 . . ? N2 C201 H20C 109.5 . . ? H20A C201 H20C 109.5 . . ? H20B C201 H20C 109.5 . . ? N2 C15 C16 111.28(12) . . ? N2 C15 H15A 109.4 . . ? C16 C15 H15A 109.4 . . ? N2 C15 H15B 109.4 . . ? C16 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? N1 C16 C15 110.91(11) . . ? N1 C16 H16A 109.5 . . ? C15 C16 H16A 109.5 . . ? N1 C16 H16B 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 108.0 . . ? C112 C111 Al1 117.44(10) . . ? C112 C111 H11A 107.9 . . ? Al1 C111 H11A 107.9 . . ? C112 C111 H11B 107.9 . . ? Al1 C111 H11B 107.9 . . ? H11A C111 H11B 107.2 . . ? C114 C112 C113 110.13(16) . . ? C114 C112 C111 111.37(15) . . ? C113 C112 C111 112.80(13) . . ? C114 C112 H112 107.4 . . ? C113 C112 H112 107.4 . . ? C111 C112 H112 107.4 . . ? C112 C113 H11C 109.5 . . ? C112 C113 H11D 109.5 . . ? H11C C113 H11D 109.5 . . ? C112 C113 H11E 109.5 . . ? H11C C113 H11E 109.5 . . ? H11D C113 H11E 109.5 . . ? C112 C114 H11F 109.5 . . ? C112 C114 H11G 109.5 . . ? H11F C114 H11G 109.5 . . ? C112 C114 H11H 109.5 . . ? H11F C114 H11H 109.5 . . ? H11G C114 H11H 109.5 . . ? C01 B1 C05 109.02(11) . . ? C01 B1 Al1 123.20(10) . . ? C05 B1 Al1 127.46(10) . . ? C01 B1 H1 112.4(7) . . ? C05 B1 H1 112.8(7) . . ? Al1 B1 H1 53.6(7) . . ? C01 B1 H2 111.3(8) . . ? C05 B1 H2 109.2(7) . . ? Al1 B1 H2 48.5(7) . . ? H1 B1 H2 102.0(10) . . ? C08 C01 C02 114.51(13) . . ? C08 C01 B1 107.39(12) . . ? C02 C01 B1 108.32(12) . . ? C08 C01 H01 108.8 . . ? C02 C01 H01 108.8 . . ? B1 C01 H01 108.8 . . ? C03 C02 C01 115.18(14) . . ? C03 C02 H02A 108.5 . . ? C01 C02 H02A 108.5 . . ? C03 C02 H02B 108.5 . . ? C01 C02 H02B 108.5 . . ? H02A C02 H02B 107.5 . . ? C04 C03 C02 114.79(13) . . ? C04 C03 H03A 108.6 . . ? C02 C03 H03A 108.6 . . ? C04 C03 H03B 108.6 . . ? C02 C03 H03B 108.6 . . ? H03A C03 H03B 107.5 . . ? C03 C04 C05 114.68(13) . . ? C03 C04 H04A 108.6 . . ? C05 C04 H04A 108.6 . . ? C03 C04 H04B 108.6 . . ? C05 C04 H04B 108.6 . . ? H04A C04 H04B 107.6 . . ? C04 C05 C06 113.77(12) . . ? C04 C05 B1 107.98(12) . . ? C06 C05 B1 108.54(11) . . ? C04 C05 H05 108.8 . . ? C06 C05 H05 108.8 . . ? B1 C05 H05 108.8 . . ? C07 C06 C05 115.62(13) . . ? C07 C06 H06A 108.4 . . ? C05 C06 H06A 108.4 . . ? C07 C06 H06B 108.4 . . ? C05 C06 H06B 108.4 . . ? H06A C06 H06B 107.4 . . ? C06 C07 C08 115.48(12) . . ? C06 C07 H07A 108.4 . . ? C08 C07 H07A 108.4 . . ? C06 C07 H07B 108.4 . . ? C08 C07 H07B 108.4 . . ? H07A C07 H07B 107.5 . . ? C07 C08 C01 115.16(12) . . ? C07 C08 H08A 108.5 . . ? C01 C08 H08A 108.5 . . ? C07 C08 H08B 108.5 . . ? C01 C08 H08B 108.5 . . ? H08A C08 H08B 107.5 . . ? C11 Si1 C103 108.27(7) . . ? C11 Si1 C101 110.01(8) . . ? C103 Si1 C101 108.68(9) . . ? C11 Si1 C102 110.71(7) . . ? C103 Si1 C102 109.36(9) . . ? C101 Si1 C102 109.76(9) . . ? Si1 C101 H10A 109.5 . . ? Si1 C101 H10B 109.5 . . ? H10A C101 H10B 109.5 . . ? Si1 C101 H10C 109.5 . . ? H10A C101 H10C 109.5 . . ? H10B C101 H10C 109.5 . . ? Si1 C102 H10D 109.5 . . ? Si1 C102 H10E 109.5 . . ? H10D C102 H10E 109.5 . . ? Si1 C102 H10F 109.5 . . ? H10D C102 H10F 109.5 . . ? H10E C102 H10F 109.5 . . ? Si1 C103 H10G 109.5 . . ? Si1 C103 H10H 109.5 . . ? H10G C103 H10H 109.5 . . ? Si1 C103 H10I 109.5 . . ? H10G C103 H10I 109.5 . . ? H10H C103 H10I 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C111 Al1 C11 C12 -95.86(11) . . . . ? N1 Al1 C11 C12 2.47(8) . . . . ? B1 Al1 C11 C12 116.38(9) . . . . ? C111 Al1 C11 Si1 85.95(15) . . . . ? N1 Al1 C11 Si1 -175.72(15) . . . . ? B1 Al1 C11 Si1 -61.81(15) . . . . ? C12 Al1 C11 Si1 -178.2(2) . . . . ? Si1 C11 C12 N1 175.13(9) . . . . ? Al1 C11 C12 N1 -3.64(12) . . . . ? Si1 C11 C12 Al1 178.77(13) . . . . ? C111 Al1 C12 C11 109.85(10) . . . . ? N1 Al1 C12 C11 -176.17(13) . . . . ? B1 Al1 C12 C11 -81.80(10) . . . . ? C111 Al1 C12 N1 -73.98(9) . . . . ? C11 Al1 C12 N1 176.17(13) . . . . ? B1 Al1 C12 N1 94.37(9) . . . . ? C11 C12 N1 C13 -115.30(13) . . . . ? Al1 C12 N1 C13 -118.76(9) . . . . ? C11 C12 N1 C16 123.19(13) . . . . ? Al1 C12 N1 C16 119.73(10) . . . . ? C11 C12 N1 Al1 3.46(12) . . . . ? C111 Al1 N1 C12 123.53(8) . . . . ? C11 Al1 N1 C12 -2.24(8) . . . . ? B1 Al1 N1 C12 -109.35(8) . . . . ? C111 Al1 N1 C13 -126.25(10) . . . . ? C11 Al1 N1 C13 107.98(10) . . . . ? B1 Al1 N1 C13 0.86(12) . . . . ? C12 Al1 N1 C13 110.22(12) . . . . ? C111 Al1 N1 C16 13.14(11) . . . . ? C11 Al1 N1 C16 -112.64(11) . . . . ? B1 Al1 N1 C16 140.25(10) . . . . ? C12 Al1 N1 C16 -110.39(12) . . . . ? C12 N1 C13 C14 179.97(10) . . . . ? C16 N1 C13 C14 -57.10(14) . . . . ? Al1 N1 C13 C14 86.48(12) . . . . ? N1 C13 C14 N2 60.29(14) . . . . ? C13 C14 N2 C15 -60.04(15) . . . . ? C13 C14 N2 C201 177.91(13) . . . . ? C201 N2 C15 C16 -178.94(11) . . . . ? C14 N2 C15 C16 58.73(14) . . . . ? C12 N1 C16 C15 178.45(11) . . . . ? C13 N1 C16 C15 55.58(14) . . . . ? Al1 N1 C16 C15 -87.62(13) . . . . ? N2 C15 C16 N1 -57.54(15) . . . . ? C11 Al1 C111 C112 -88.77(13) . . . . ? N1 Al1 C111 C112 -168.82(11) . . . . ? B1 Al1 C111 C112 59.66(13) . . . . ? C12 Al1 C111 C112 -130.67(11) . . . . ? Al1 C111 C112 C114 61.26(19) . . . . ? Al1 C111 C112 C113 -174.32(12) . . . . ? C111 Al1 B1 C01 -171.34(11) . . . . ? C11 Al1 B1 C01 -17.79(13) . . . . ? N1 Al1 B1 C01 62.94(13) . . . . ? C12 Al1 B1 C01 18.93(14) . . . . ? C111 Al1 B1 C05 15.86(14) . . . . ? C11 Al1 B1 C05 169.41(11) . . . . ? N1 Al1 B1 C05 -109.86(12) . . . . ? C12 Al1 B1 C05 -153.87(11) . . . . ? C05 B1 C01 C08 -63.33(14) . . . . ? Al1 B1 C01 C08 122.71(12) . . . . ? C05 B1 C01 C02 60.84(15) . . . . ? Al1 B1 C01 C02 -113.12(12) . . . . ? C08 C01 C02 C03 67.84(19) . . . . ? B1 C01 C02 C03 -51.96(18) . . . . ? C01 C02 C03 C04 44.5(2) . . . . ? C02 C03 C04 C05 -45.7(2) . . . . ? C03 C04 C05 C06 -66.32(17) . . . . ? C03 C04 C05 B1 54.21(17) . . . . ? C01 B1 C05 C04 -62.03(14) . . . . ? Al1 B1 C05 C04 111.61(13) . . . . ? C01 B1 C05 C06 61.74(15) . . . . ? Al1 B1 C05 C06 -124.63(12) . . . . ? C04 C05 C06 C07 70.16(17) . . . . ? B1 C05 C06 C07 -50.06(17) . . . . ? C05 C06 C07 C08 40.8(2) . . . . ? C06 C07 C08 C01 -42.8(2) . . . . ? C02 C01 C08 C07 -66.68(19) . . . . ? B1 C01 C08 C07 53.64(17) . . . . ? C12 C11 Si1 C103 -106.50(14) . . . . ? Al1 C11 Si1 C103 71.33(15) . . . . ? C12 C11 Si1 C101 134.87(13) . . . . ? Al1 C11 Si1 C101 -47.30(15) . . . . ? C12 C11 Si1 C102 13.37(15) . . . . ? Al1 C11 Si1 C102 -168.79(13) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.95 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.411 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.038