# 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_cj038_0m _database_code_depnum_ccdc_archive 'CCDC 910001' #TrackingRef 'CIFs-revised.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H31 B F10 N P' _chemical_formula_weight 685.38 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.0192(10) _cell_length_b 17.8227(15) _cell_length_c 16.3592(15) _cell_angle_alpha 90.00 _cell_angle_beta 106.482(3) _cell_angle_gamma 90.00 _cell_volume 3080.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9869 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 27.51 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.177 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27638 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 27.56 _reflns_number_total 7101 _reflns_number_gt 5916 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0394P)^2^+1.3766P] 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 7101 _refine_ls_number_parameters 430 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0891 _refine_ls_wR_factor_gt 0.0830 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.38359(12) 0.28843(8) 0.08214(8) 0.0178(3) Uani 1 1 d . . . H29 H 0.3928 0.3395 0.1035 0.021 Uiso 1 1 calc R . . H30 H 0.4094 0.2872 0.0302 0.021 Uiso 1 1 calc R . . C2 C 0.24443(12) 0.26441(7) 0.06246(8) 0.0166(3) Uani 1 1 d . . . H10 H 0.2381 0.2185 0.0285 0.020 Uiso 1 1 calc R . . C3 C 0.14773(13) 0.31768(8) 0.00706(8) 0.0193(3) Uani 1 1 d . . . C4 C 0.17321(14) 0.39328(9) -0.00098(9) 0.0252(3) Uani 1 1 d . . . H9 H 0.2521 0.4125 0.0282 0.030 Uiso 1 1 calc R . . C5 C 0.08265(16) 0.44067(9) -0.05198(10) 0.0313(4) Uani 1 1 d . . . H6 H 0.1011 0.4912 -0.0561 0.038 Uiso 1 1 calc R . . C6 C -0.03435(16) 0.41314(10) -0.09641(10) 0.0342(4) Uani 1 1 d . . . H1 H -0.0954 0.4451 -0.1297 0.041 Uiso 1 1 calc R . . C7 C -0.06023(16) 0.33793(10) -0.09116(10) 0.0335(4) Uani 1 1 d . . . H8 H -0.1387 0.3189 -0.1214 0.040 Uiso 1 1 calc R . . C8 C 0.03052(14) 0.29053(9) -0.04094(9) 0.0248(3) Uani 1 1 d . . . H7 H 0.0129 0.2396 -0.0393 0.030 Uiso 1 1 calc R . . C9 C 0.11054(13) 0.15700(8) 0.15472(9) 0.0217(3) Uani 1 1 d . . . C10 C 0.12041(15) 0.10398(8) 0.08259(10) 0.0270(3) Uani 1 1 d . . . H26 H 0.0682 0.0607 0.0817 0.040 Uiso 1 1 calc R . . H27 H 0.2068 0.0885 0.0922 0.040 Uiso 1 1 calc R . . H28 H 0.0924 0.1297 0.0289 0.040 Uiso 1 1 calc R . . C11 C -0.02297(14) 0.19182(9) 0.13052(10) 0.0286(3) Uani 1 1 d . . . H20 H -0.0299 0.2285 0.0865 0.043 Uiso 1 1 calc R . . H21 H -0.0373 0.2155 0.1797 0.043 Uiso 1 1 calc R . . H22 H -0.0849 0.1532 0.1103 0.043 Uiso 1 1 calc R . . C12 C 0.12433(15) 0.10888(9) 0.23531(10) 0.0273(3) Uani 1 1 d . . . H23 H 0.1986 0.0781 0.2452 0.041 Uiso 1 1 calc R . . H24 H 0.0511 0.0775 0.2274 0.041 Uiso 1 1 calc R . . H25 H 0.1318 0.1411 0.2835 0.041 Uiso 1 1 calc R . . C13 C 0.20226(13) 0.31198(8) 0.23389(9) 0.0201(3) Uani 1 1 d . . . C14 C 0.17193(15) 0.28403(9) 0.31451(9) 0.0284(3) Uani 1 1 d . . . H17 H 0.1676 0.3260 0.3504 0.043 Uiso 1 1 calc R . . H18 H 0.2371 0.2502 0.3448 0.043 Uiso 1 1 calc R . . H19 H 0.0921 0.2583 0.2989 0.043 Uiso 1 1 calc R . . C15 C 0.09316(15) 0.36292(9) 0.18516(10) 0.0311(4) Uani 1 1 d . . . H11 H 0.0781 0.4007 0.2229 0.047 Uiso 1 1 calc R . . H12 H 0.0180 0.3334 0.1635 0.047 Uiso 1 1 calc R . . H13 H 0.1152 0.3865 0.1386 0.047 Uiso 1 1 calc R . . C16 C 0.32238(15) 0.35984(9) 0.26094(10) 0.0281(3) Uani 1 1 d . . . H14 H 0.3924 0.3291 0.2911 0.042 Uiso 1 1 calc R . . H15 H 0.3106 0.3997 0.2974 0.042 Uiso 1 1 calc R . . H16 H 0.3395 0.3807 0.2113 0.042 Uiso 1 1 calc R . . C17 C 0.41040(12) 0.13581(7) 0.25810(8) 0.0164(3) Uani 1 1 d . . . C18 C 0.42709(13) 0.14291(8) 0.34526(9) 0.0209(3) Uani 1 1 d . . . H4 H 0.4190 0.1897 0.3684 0.025 Uiso 1 1 calc R . . C19 C 0.45582(16) 0.08047(9) 0.39787(9) 0.0289(3) Uani 1 1 d . . . H5 H 0.4666 0.0857 0.4561 0.035 Uiso 1 1 calc R . . C20 C 0.46861(16) 0.01066(9) 0.36464(10) 0.0298(3) Uani 1 1 d . . . H2 H 0.4877 -0.0310 0.4002 0.036 Uiso 1 1 calc R . . C21 C 0.45284(14) 0.00304(8) 0.27813(10) 0.0235(3) Uani 1 1 d . . . H3 H 0.4618 -0.0438 0.2555 0.028 Uiso 1 1 calc R . . C22 C 0.42372(12) 0.06499(8) 0.22518(9) 0.0188(3) Uani 1 1 d . . . H31 H 0.4129 0.0594 0.1670 0.023 Uiso 1 1 calc R . . C23 C 0.59570(12) 0.28521(7) 0.20941(9) 0.0185(3) Uani 1 1 d . . . C24 C 0.64351(13) 0.29502(8) 0.29669(9) 0.0210(3) Uani 1 1 d . . . C25 C 0.74589(14) 0.34019(8) 0.33543(10) 0.0254(3) Uani 1 1 d . . . C26 C 0.80633(13) 0.37951(8) 0.28649(11) 0.0278(3) Uani 1 1 d . . . C27 C 0.76345(14) 0.37277(8) 0.19964(11) 0.0269(3) Uani 1 1 d . . . C28 C 0.66297(13) 0.32589(8) 0.16379(9) 0.0222(3) Uani 1 1 d . . . C29 C 0.54316(12) 0.16359(8) 0.11440(8) 0.0173(3) Uani 1 1 d . . . C30 C 0.64639(13) 0.12463(8) 0.16600(8) 0.0189(3) Uani 1 1 d . . . C31 C 0.71068(13) 0.06882(8) 0.13795(9) 0.0211(3) Uani 1 1 d . . . C32 C 0.67455(14) 0.04903(8) 0.05339(10) 0.0255(3) Uani 1 1 d . . . C33 C 0.57360(14) 0.08496(8) -0.00102(9) 0.0238(3) Uani 1 1 d . . . C34 C 0.51012(13) 0.13988(8) 0.03016(9) 0.0204(3) Uani 1 1 d . . . N1 N 0.37920(10) 0.19937(6) 0.20139(7) 0.0154(2) Uani 1 1 d . . . B1 B 0.47484(14) 0.23269(9) 0.15311(9) 0.0159(3) Uani 1 1 d . . . F1 F 0.59220(8) 0.25873(5) 0.35086(5) 0.0287(2) Uani 1 1 d . . . F2 F 0.78657(9) 0.34586(6) 0.42104(6) 0.0359(2) Uani 1 1 d . . . F3 F 0.90487(9) 0.42423(6) 0.32338(7) 0.0419(3) Uani 1 1 d . . . F4 F 0.81702(9) 0.41303(6) 0.14967(7) 0.0394(2) Uani 1 1 d . . . F5 F 0.63005(8) 0.32087(5) 0.07785(5) 0.0305(2) Uani 1 1 d . . . F6 F 0.68804(8) 0.13980(5) 0.25070(5) 0.02466(19) Uani 1 1 d . . . F7 F 0.80870(8) 0.03318(5) 0.19239(6) 0.0308(2) Uani 1 1 d . . . F8 F 0.73620(10) -0.00511(6) 0.02454(7) 0.0410(3) Uani 1 1 d . . . F9 F 0.53722(10) 0.06638(6) -0.08413(6) 0.0357(2) Uani 1 1 d . . . F10 F 0.40916(8) 0.16986(5) -0.02805(5) 0.0296(2) Uani 1 1 d . . . P1 P 0.23334(3) 0.232404(19) 0.16753(2) 0.01496(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0165(6) 0.0213(7) 0.0166(6) 0.0037(5) 0.0062(5) -0.0001(5) C2 0.0180(6) 0.0190(6) 0.0131(6) 0.0010(5) 0.0048(5) 0.0010(5) C3 0.0197(6) 0.0254(7) 0.0138(6) 0.0024(5) 0.0063(5) 0.0049(5) C4 0.0254(7) 0.0272(8) 0.0244(7) 0.0051(6) 0.0092(6) 0.0032(6) C5 0.0394(9) 0.0279(8) 0.0308(8) 0.0112(6) 0.0166(7) 0.0101(7) C6 0.0329(9) 0.0432(10) 0.0247(8) 0.0101(7) 0.0051(7) 0.0177(7) C7 0.0257(8) 0.0450(10) 0.0248(8) 0.0025(7) -0.0010(6) 0.0066(7) C8 0.0244(7) 0.0296(8) 0.0188(7) 0.0006(6) 0.0034(6) 0.0034(6) C9 0.0195(7) 0.0238(7) 0.0220(7) 0.0010(5) 0.0061(5) -0.0052(5) C10 0.0292(8) 0.0236(7) 0.0257(7) -0.0025(6) 0.0039(6) -0.0060(6) C11 0.0184(7) 0.0362(9) 0.0304(8) 0.0032(7) 0.0058(6) -0.0046(6) C12 0.0260(7) 0.0297(8) 0.0275(8) 0.0063(6) 0.0100(6) -0.0073(6) C13 0.0210(7) 0.0223(7) 0.0183(6) -0.0020(5) 0.0076(5) 0.0034(5) C14 0.0321(8) 0.0356(9) 0.0205(7) -0.0030(6) 0.0126(6) 0.0008(7) C15 0.0326(8) 0.0342(9) 0.0254(8) -0.0035(6) 0.0065(6) 0.0138(7) C16 0.0300(8) 0.0246(8) 0.0315(8) -0.0103(6) 0.0119(6) -0.0040(6) C17 0.0150(6) 0.0185(6) 0.0155(6) 0.0031(5) 0.0040(5) 0.0001(5) C18 0.0247(7) 0.0211(7) 0.0171(6) 0.0005(5) 0.0062(5) -0.0015(6) C19 0.0391(9) 0.0313(8) 0.0151(6) 0.0051(6) 0.0055(6) -0.0029(7) C20 0.0365(9) 0.0242(8) 0.0260(8) 0.0113(6) 0.0048(6) 0.0006(7) C21 0.0233(7) 0.0184(7) 0.0284(8) 0.0022(6) 0.0068(6) 0.0008(6) C22 0.0184(6) 0.0222(7) 0.0163(6) -0.0001(5) 0.0057(5) -0.0013(5) C23 0.0157(6) 0.0170(6) 0.0222(7) 0.0007(5) 0.0043(5) 0.0023(5) C24 0.0191(6) 0.0205(7) 0.0229(7) 0.0011(5) 0.0051(5) 0.0010(5) C25 0.0208(7) 0.0245(7) 0.0266(7) -0.0059(6) -0.0002(6) 0.0031(6) C26 0.0157(7) 0.0205(7) 0.0443(9) -0.0057(6) 0.0037(6) -0.0025(6) C27 0.0184(7) 0.0232(7) 0.0415(9) 0.0060(6) 0.0125(6) 0.0000(6) C28 0.0189(7) 0.0235(7) 0.0240(7) 0.0034(6) 0.0056(5) 0.0027(6) C29 0.0157(6) 0.0208(7) 0.0163(6) 0.0008(5) 0.0061(5) -0.0014(5) C30 0.0179(6) 0.0220(7) 0.0162(6) -0.0005(5) 0.0038(5) -0.0036(5) C31 0.0161(6) 0.0198(7) 0.0268(7) 0.0033(5) 0.0051(5) 0.0002(5) C32 0.0267(7) 0.0216(7) 0.0329(8) -0.0039(6) 0.0162(6) 0.0018(6) C33 0.0292(7) 0.0275(8) 0.0164(6) -0.0038(6) 0.0091(6) -0.0023(6) C34 0.0194(7) 0.0251(7) 0.0165(6) 0.0025(5) 0.0050(5) 0.0004(5) N1 0.0161(5) 0.0164(5) 0.0141(5) 0.0024(4) 0.0046(4) 0.0006(4) B1 0.0152(7) 0.0194(7) 0.0130(6) 0.0010(5) 0.0040(5) -0.0001(6) F1 0.0297(5) 0.0374(5) 0.0174(4) 0.0012(4) 0.0038(3) -0.0078(4) F2 0.0302(5) 0.0436(6) 0.0273(5) -0.0116(4) -0.0025(4) -0.0033(4) F3 0.0250(5) 0.0355(5) 0.0605(7) -0.0113(5) 0.0047(4) -0.0125(4) F4 0.0263(5) 0.0403(6) 0.0547(6) 0.0133(5) 0.0168(4) -0.0071(4) F5 0.0259(4) 0.0433(5) 0.0241(4) 0.0066(4) 0.0098(4) -0.0045(4) F6 0.0244(4) 0.0289(4) 0.0164(4) -0.0030(3) -0.0012(3) 0.0022(4) F7 0.0223(4) 0.0280(5) 0.0380(5) 0.0036(4) 0.0019(4) 0.0078(4) F8 0.0450(6) 0.0377(6) 0.0439(6) -0.0098(5) 0.0184(5) 0.0150(5) F9 0.0480(6) 0.0412(6) 0.0188(4) -0.0086(4) 0.0111(4) 0.0050(5) F10 0.0300(5) 0.0399(5) 0.0147(4) -0.0011(4) -0.0005(3) 0.0103(4) P1 0.01494(16) 0.01722(16) 0.01305(15) 0.00053(12) 0.00452(12) -0.00046(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.5356(18) . ? C1 B1 1.6381(19) . ? C1 H29 0.9700 . ? C1 H30 0.9700 . ? C2 C3 1.5199(18) . ? C2 P1 1.8477(13) . ? C2 H10 0.9800 . ? C3 C4 1.390(2) . ? C3 C8 1.394(2) . ? C4 C5 1.390(2) . ? C4 H9 0.9300 . ? C5 C6 1.378(2) . ? C5 H6 0.9300 . ? C6 C7 1.378(3) . ? C6 H1 0.9300 . ? C7 C8 1.386(2) . ? C7 H8 0.9300 . ? C8 H7 0.9300 . ? C9 C10 1.539(2) . ? C9 C11 1.541(2) . ? C9 C12 1.544(2) . ? C9 P1 1.8763(14) . ? C10 H26 0.9600 . ? C10 H27 0.9600 . ? C10 H28 0.9600 . ? C11 H20 0.9600 . ? C11 H21 0.9600 . ? C11 H22 0.9600 . ? C12 H23 0.9600 . ? C12 H24 0.9600 . ? C12 H25 0.9600 . ? C13 C16 1.531(2) . ? C13 C14 1.533(2) . ? C13 C15 1.537(2) . ? C13 P1 1.8756(14) . ? C14 H17 0.9600 . ? C14 H18 0.9600 . ? C14 H19 0.9600 . ? C15 H11 0.9600 . ? C15 H12 0.9600 . ? C15 H13 0.9600 . ? C16 H14 0.9600 . ? C16 H15 0.9600 . ? C16 H16 0.9600 . ? C17 C18 1.3908(19) . ? C17 C22 1.3962(19) . ? C17 N1 1.4426(16) . ? C18 C19 1.387(2) . ? C18 H4 0.9300 . ? C19 C20 1.381(2) . ? C19 H5 0.9300 . ? C20 C21 1.383(2) . ? C20 H2 0.9300 . ? C21 C22 1.3837(19) . ? C21 H3 0.9300 . ? C22 H31 0.9300 . ? C23 C24 1.3857(19) . ? C23 C28 1.395(2) . ? C23 B1 1.6740(19) . ? C24 F1 1.3443(17) . ? C24 C25 1.385(2) . ? C25 F2 1.3478(17) . ? C25 C26 1.370(2) . ? C26 F3 1.3441(16) . ? C26 C27 1.369(2) . ? C27 F4 1.3436(18) . ? C27 C28 1.378(2) . ? C28 F5 1.3515(17) . ? C29 C34 1.3875(19) . ? C29 C30 1.3943(19) . ? C29 B1 1.660(2) . ? C30 F6 1.3575(15) . ? C30 C31 1.373(2) . ? C31 F7 1.3481(16) . ? C31 C32 1.373(2) . ? C32 F8 1.3407(17) . ? C32 C33 1.370(2) . ? C33 F9 1.3452(16) . ? C33 C34 1.382(2) . ? C34 F10 1.3524(15) . ? N1 B1 1.5998(18) . ? N1 P1 1.6527(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 B1 110.81(11) . . ? C2 C1 H29 109.5 . . ? B1 C1 H29 109.5 . . ? C2 C1 H30 109.5 . . ? B1 C1 H30 109.5 . . ? H29 C1 H30 108.1 . . ? C3 C2 C1 116.12(11) . . ? C3 C2 P1 121.83(10) . . ? C1 C2 P1 102.51(8) . . ? C3 C2 H10 104.9 . . ? C1 C2 H10 104.9 . . ? P1 C2 H10 104.9 . . ? C4 C3 C8 117.56(13) . . ? C4 C3 C2 122.39(12) . . ? C8 C3 C2 119.99(13) . . ? C3 C4 C5 121.05(14) . . ? C3 C4 H9 119.5 . . ? C5 C4 H9 119.5 . . ? C6 C5 C4 120.33(15) . . ? C6 C5 H6 119.8 . . ? C4 C5 H6 119.8 . . ? C5 C6 C7 119.50(14) . . ? C5 C6 H1 120.2 . . ? C7 C6 H1 120.2 . . ? C6 C7 C8 120.15(15) . . ? C6 C7 H8 119.9 . . ? C8 C7 H8 119.9 . . ? C7 C8 C3 121.30(15) . . ? C7 C8 H7 119.3 . . ? C3 C8 H7 119.3 . . ? C10 C9 C11 108.67(12) . . ? C10 C9 C12 107.60(12) . . ? C11 C9 C12 107.37(12) . . ? C10 C9 P1 108.65(10) . . ? C11 C9 P1 110.23(10) . . ? C12 C9 P1 114.17(10) . . ? C9 C10 H26 109.5 . . ? C9 C10 H27 109.5 . . ? H26 C10 H27 109.5 . . ? C9 C10 H28 109.5 . . ? H26 C10 H28 109.5 . . ? H27 C10 H28 109.5 . . ? C9 C11 H20 109.5 . . ? C9 C11 H21 109.5 . . ? H20 C11 H21 109.5 . . ? C9 C11 H22 109.5 . . ? H20 C11 H22 109.5 . . ? H21 C11 H22 109.5 . . ? C9 C12 H23 109.5 . . ? C9 C12 H24 109.5 . . ? H23 C12 H24 109.5 . . ? C9 C12 H25 109.5 . . ? H23 C12 H25 109.5 . . ? H24 C12 H25 109.5 . . ? C16 C13 C14 108.30(12) . . ? C16 C13 C15 107.80(12) . . ? C14 C13 C15 107.99(12) . . ? C16 C13 P1 107.69(10) . . ? C14 C13 P1 111.87(10) . . ? C15 C13 P1 113.02(10) . . ? C13 C14 H17 109.5 . . ? C13 C14 H18 109.5 . . ? H17 C14 H18 109.5 . . ? C13 C14 H19 109.5 . . ? H17 C14 H19 109.5 . . ? H18 C14 H19 109.5 . . ? C13 C15 H11 109.5 . . ? C13 C15 H12 109.5 . . ? H11 C15 H12 109.5 . . ? C13 C15 H13 109.5 . . ? H11 C15 H13 109.5 . . ? H12 C15 H13 109.5 . . ? C13 C16 H14 109.5 . . ? C13 C16 H15 109.5 . . ? H14 C16 H15 109.5 . . ? C13 C16 H16 109.5 . . ? H14 C16 H16 109.5 . . ? H15 C16 H16 109.5 . . ? C18 C17 C22 118.68(12) . . ? C18 C17 N1 121.73(12) . . ? C22 C17 N1 119.59(11) . . ? C19 C18 C17 120.24(14) . . ? C19 C18 H4 119.9 . . ? C17 C18 H4 119.9 . . ? C20 C19 C18 120.62(14) . . ? C20 C19 H5 119.7 . . ? C18 C19 H5 119.7 . . ? C19 C20 C21 119.62(14) . . ? C19 C20 H2 120.2 . . ? C21 C20 H2 120.2 . . ? C20 C21 C22 120.12(14) . . ? C20 C21 H3 119.9 . . ? C22 C21 H3 119.9 . . ? C21 C22 C17 120.73(13) . . ? C21 C22 H31 119.6 . . ? C17 C22 H31 119.6 . . ? C24 C23 C28 112.42(12) . . ? C24 C23 B1 130.39(12) . . ? C28 C23 B1 117.19(12) . . ? F1 C24 C25 114.74(13) . . ? F1 C24 C23 120.70(12) . . ? C25 C24 C23 124.55(14) . . ? F2 C25 C26 119.69(13) . . ? F2 C25 C24 120.45(14) . . ? C26 C25 C24 119.86(14) . . ? F3 C26 C27 120.99(15) . . ? F3 C26 C25 120.37(15) . . ? C27 C26 C25 118.64(13) . . ? F4 C27 C26 120.16(14) . . ? F4 C27 C28 120.23(15) . . ? C26 C27 C28 119.59(14) . . ? F5 C28 C27 115.40(13) . . ? F5 C28 C23 119.70(12) . . ? C27 C28 C23 124.90(14) . . ? C34 C29 C30 112.87(12) . . ? C34 C29 B1 125.82(12) . . ? C30 C29 B1 121.26(12) . . ? F6 C30 C31 115.36(12) . . ? F6 C30 C29 120.02(12) . . ? C31 C30 C29 124.61(13) . . ? F7 C31 C32 119.58(13) . . ? F7 C31 C30 120.87(13) . . ? C32 C31 C30 119.55(13) . . ? F8 C32 C33 120.44(14) . . ? F8 C32 C31 120.57(14) . . ? C33 C32 C31 118.98(13) . . ? F9 C33 C32 119.71(13) . . ? F9 C33 C34 120.70(13) . . ? C32 C33 C34 119.58(13) . . ? F10 C34 C33 114.91(12) . . ? F10 C34 C29 120.71(12) . . ? C33 C34 C29 124.38(13) . . ? C17 N1 B1 122.60(10) . . ? C17 N1 P1 121.80(9) . . ? B1 N1 P1 114.61(8) . . ? N1 B1 C1 102.54(10) . . ? N1 B1 C29 110.28(11) . . ? C1 B1 C29 115.67(11) . . ? N1 B1 C23 117.94(11) . . ? C1 B1 C23 106.46(11) . . ? C29 B1 C23 104.40(10) . . ? N1 P1 C2 96.15(6) . . ? N1 P1 C13 113.29(6) . . ? C2 P1 C13 112.09(6) . . ? N1 P1 C9 112.60(6) . . ? C2 P1 C9 110.68(6) . . ? C13 P1 C9 111.22(7) . . ? 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 B1 C1 C2 C3 171.72(11) . . . . ? B1 C1 C2 P1 36.44(12) . . . . ? C1 C2 C3 C4 -22.08(19) . . . . ? P1 C2 C3 C4 103.97(15) . . . . ? C1 C2 C3 C8 155.07(13) . . . . ? P1 C2 C3 C8 -78.88(16) . . . . ? C8 C3 C4 C5 3.0(2) . . . . ? C2 C3 C4 C5 -179.82(14) . . . . ? C3 C4 C5 C6 -0.6(2) . . . . ? C4 C5 C6 C7 -1.2(3) . . . . ? C5 C6 C7 C8 0.6(3) . . . . ? C6 C7 C8 C3 1.9(2) . . . . ? C4 C3 C8 C7 -3.6(2) . . . . ? C2 C3 C8 C7 179.11(14) . . . . ? C22 C17 C18 C19 -0.3(2) . . . . ? N1 C17 C18 C19 179.36(13) . . . . ? C17 C18 C19 C20 0.2(2) . . . . ? C18 C19 C20 C21 0.1(3) . . . . ? C19 C20 C21 C22 -0.4(2) . . . . ? C20 C21 C22 C17 0.3(2) . . . . ? C18 C17 C22 C21 0.1(2) . . . . ? N1 C17 C22 C21 -179.60(12) . . . . ? C28 C23 C24 F1 -178.50(12) . . . . ? B1 C23 C24 F1 0.5(2) . . . . ? C28 C23 C24 C25 0.4(2) . . . . ? B1 C23 C24 C25 179.43(13) . . . . ? F1 C24 C25 F2 -0.5(2) . . . . ? C23 C24 C25 F2 -179.44(13) . . . . ? F1 C24 C25 C26 179.56(13) . . . . ? C23 C24 C25 C26 0.6(2) . . . . ? F2 C25 C26 F3 -0.7(2) . . . . ? C24 C25 C26 F3 179.20(13) . . . . ? F2 C25 C26 C27 179.88(13) . . . . ? C24 C25 C26 C27 -0.2(2) . . . . ? F3 C26 C27 F4 -2.3(2) . . . . ? C25 C26 C27 F4 177.11(13) . . . . ? F3 C26 C27 C28 179.37(13) . . . . ? C25 C26 C27 C28 -1.3(2) . . . . ? F4 C27 C28 F5 3.8(2) . . . . ? C26 C27 C28 F5 -177.84(13) . . . . ? F4 C27 C28 C23 -175.92(13) . . . . ? C26 C27 C28 C23 2.4(2) . . . . ? C24 C23 C28 F5 178.38(12) . . . . ? B1 C23 C28 F5 -0.81(19) . . . . ? C24 C23 C28 C27 -1.9(2) . . . . ? B1 C23 C28 C27 178.89(13) . . . . ? C34 C29 C30 F6 -178.09(12) . . . . ? B1 C29 C30 F6 4.04(19) . . . . ? C34 C29 C30 C31 0.4(2) . . . . ? B1 C29 C30 C31 -177.48(13) . . . . ? F6 C30 C31 F7 -0.56(19) . . . . ? C29 C30 C31 F7 -179.10(13) . . . . ? F6 C30 C31 C32 179.36(13) . . . . ? C29 C30 C31 C32 0.8(2) . . . . ? F7 C31 C32 F8 -0.3(2) . . . . ? C30 C31 C32 F8 179.78(13) . . . . ? F7 C31 C32 C33 179.06(13) . . . . ? C30 C31 C32 C33 -0.9(2) . . . . ? F8 C32 C33 F9 -0.8(2) . . . . ? C31 C32 C33 F9 179.80(13) . . . . ? F8 C32 C33 C34 179.07(14) . . . . ? C31 C32 C33 C34 -0.3(2) . . . . ? F9 C33 C34 F10 2.3(2) . . . . ? C32 C33 C34 F10 -177.64(13) . . . . ? F9 C33 C34 C29 -178.46(13) . . . . ? C32 C33 C34 C29 1.6(2) . . . . ? C30 C29 C34 F10 177.62(12) . . . . ? B1 C29 C34 F10 -4.6(2) . . . . ? C30 C29 C34 C33 -1.6(2) . . . . ? B1 C29 C34 C33 176.13(13) . . . . ? C18 C17 N1 B1 112.57(15) . . . . ? C22 C17 N1 B1 -67.78(16) . . . . ? C18 C17 N1 P1 -79.41(15) . . . . ? C22 C17 N1 P1 100.23(13) . . . . ? C17 N1 B1 C1 167.03(11) . . . . ? P1 N1 B1 C1 -1.78(12) . . . . ? C17 N1 B1 C29 43.30(15) . . . . ? P1 N1 B1 C29 -125.51(9) . . . . ? C17 N1 B1 C23 -76.45(16) . . . . ? P1 N1 B1 C23 114.75(11) . . . . ? C2 C1 B1 N1 -23.69(14) . . . . ? C2 C1 B1 C29 96.36(13) . . . . ? C2 C1 B1 C23 -148.19(11) . . . . ? C34 C29 B1 N1 101.41(15) . . . . ? C30 C29 B1 N1 -81.02(15) . . . . ? C34 C29 B1 C1 -14.34(19) . . . . ? C30 C29 B1 C1 163.23(12) . . . . ? C34 C29 B1 C23 -130.96(13) . . . . ? C30 C29 B1 C23 46.62(16) . . . . ? C24 C23 B1 N1 13.4(2) . . . . ? C28 C23 B1 N1 -167.58(12) . . . . ? C24 C23 B1 C1 127.80(15) . . . . ? C28 C23 B1 C1 -53.18(15) . . . . ? C24 C23 B1 C29 -109.36(15) . . . . ? C28 C23 B1 C29 69.65(14) . . . . ? C17 N1 P1 C2 -148.13(10) . . . . ? B1 N1 P1 C2 20.77(10) . . . . ? C17 N1 P1 C13 94.60(11) . . . . ? B1 N1 P1 C13 -96.49(10) . . . . ? C17 N1 P1 C9 -32.70(12) . . . . ? B1 N1 P1 C9 136.21(9) . . . . ? C3 C2 P1 N1 -165.13(11) . . . . ? C1 C2 P1 N1 -33.17(9) . . . . ? C3 C2 P1 C13 -46.92(12) . . . . ? C1 C2 P1 C13 85.05(10) . . . . ? C3 C2 P1 C9 77.89(12) . . . . ? C1 C2 P1 C9 -150.15(9) . . . . ? C16 C13 P1 N1 37.16(12) . . . . ? C14 C13 P1 N1 -81.73(11) . . . . ? C15 C13 P1 N1 156.12(10) . . . . ? C16 C13 P1 C2 -70.32(11) . . . . ? C14 C13 P1 C2 170.79(10) . . . . ? C15 C13 P1 C2 48.64(12) . . . . ? C16 C13 P1 C9 165.18(10) . . . . ? C14 C13 P1 C9 46.29(12) . . . . ? C15 C13 P1 C9 -75.86(12) . . . . ? C10 C9 P1 N1 -65.83(11) . . . . ? C11 C9 P1 N1 175.19(10) . . . . ? C12 C9 P1 N1 54.25(12) . . . . ? C10 C9 P1 C2 40.49(11) . . . . ? C11 C9 P1 C2 -78.49(11) . . . . ? C12 C9 P1 C2 160.57(11) . . . . ? C10 C9 P1 C13 165.78(9) . . . . ? C11 C9 P1 C13 46.80(12) . . . . ? C12 C9 P1 C13 -74.13(12) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.323 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.046 data_cj054_0m _database_code_depnum_ccdc_archive 'CCDC 910002' #TrackingRef 'CIFs-revised.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H29 B F10 N P' _chemical_formula_weight 623.31 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 9.8983(15) _cell_length_b 10.3188(14) _cell_length_c 15.235(2) _cell_angle_alpha 88.992(4) _cell_angle_beta 87.851(5) _cell_angle_gamma 63.756(4) _cell_volume 1394.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9780 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 27.58 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.187 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9636 _exptl_absorpt_correction_T_max 0.9816 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22996 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 27.60 _reflns_number_total 6295 _reflns_number_gt 5317 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0724P)^2^+0.6133P] 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 6295 _refine_ls_number_parameters 384 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1265 _refine_ls_wR_factor_gt 0.1176 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.93146(17) 0.74012(17) 0.86682(10) 0.0189(3) Uani 1 1 d . . . C2 C 0.89696(18) 0.84714(17) 0.92834(11) 0.0203(3) Uani 1 1 d . . . C3 C 0.96536(19) 0.82963(18) 1.00824(11) 0.0218(3) Uani 1 1 d . . . C4 C 1.0754(2) 0.69611(19) 1.03109(11) 0.0250(4) Uani 1 1 d . . . C5 C 1.1130(2) 0.58335(18) 0.97372(12) 0.0267(4) Uani 1 1 d . . . C6 C 1.04126(19) 0.60664(18) 0.89507(11) 0.0233(3) Uani 1 1 d . . . C7 C 0.99017(17) 0.66551(16) 0.69754(10) 0.0177(3) Uani 1 1 d . . . C8 C 1.11142(19) 0.69910(18) 0.68748(11) 0.0216(3) Uani 1 1 d . . . C9 C 1.2343(2) 0.6284(2) 0.63123(12) 0.0267(4) Uani 1 1 d . . . C10 C 1.2425(2) 0.5162(2) 0.58096(12) 0.0267(4) Uani 1 1 d . . . C11 C 1.1269(2) 0.47734(17) 0.58805(11) 0.0228(3) Uani 1 1 d . . . C12 C 1.00517(18) 0.55142(17) 0.64429(11) 0.0202(3) Uani 1 1 d . . . C13 C 0.79889(18) 1.00604(16) 0.69058(11) 0.0194(3) Uani 1 1 d . . . C14 C 0.8365(2) 1.10121(19) 0.73514(12) 0.0284(4) Uani 1 1 d . . . H28 H 0.8355 1.1002 0.7975 0.034 Uiso 1 1 calc R . . C15 C 0.8753(2) 1.1977(2) 0.68924(14) 0.0353(4) Uani 1 1 d . . . H29 H 0.9011 1.2620 0.7205 0.042 Uiso 1 1 calc R . . C16 C 0.8769(2) 1.2011(2) 0.59903(14) 0.0363(5) Uani 1 1 d . . . H2 H 0.9018 1.2686 0.5678 0.044 Uiso 1 1 calc R . . C17 C 0.8421(3) 1.1054(2) 0.55429(13) 0.0373(5) Uani 1 1 d . . . H26 H 0.8435 1.1065 0.4919 0.045 Uiso 1 1 calc R . . C18 C 0.8050(2) 1.0074(2) 0.59985(12) 0.0279(4) Uani 1 1 d . . . H27 H 0.7835 0.9405 0.5683 0.033 Uiso 1 1 calc R . . C19 C 0.72866(18) 0.68655(16) 0.78555(11) 0.0199(3) Uani 1 1 d . . . H24 H 0.7129 0.6484 0.7297 0.024 Uiso 1 1 calc R . . H25 H 0.7652 0.6068 0.8289 0.024 Uiso 1 1 calc R . . C20 C 0.57920(18) 0.81053(16) 0.81961(10) 0.0184(3) Uani 1 1 d . . . H3 H 0.5928 0.8307 0.8818 0.022 Uiso 1 1 calc R . . C21 C 0.44111(19) 0.77919(18) 0.81820(11) 0.0229(3) Uani 1 1 d . . . H8 H 0.3493 0.8695 0.8317 0.027 Uiso 1 1 calc R . . H9 H 0.4325 0.7487 0.7582 0.027 Uiso 1 1 calc R . . C22 C 0.4478(2) 0.66247(19) 0.88328(12) 0.0276(4) Uani 1 1 d . . . H4 H 0.3705 0.6306 0.8687 0.033 Uiso 1 1 calc R . . H7 H 0.5477 0.5780 0.8771 0.033 Uiso 1 1 calc R . . C23 C 0.4220(2) 0.7134(2) 0.97738(13) 0.0337(4) Uani 1 1 d . . . H1 H 0.4308 0.6336 1.0163 0.051 Uiso 1 1 calc R . . H5 H 0.3209 0.7936 0.9848 0.051 Uiso 1 1 calc R . . H6 H 0.4974 0.7461 0.9921 0.051 Uiso 1 1 calc R . . C24 C 0.47858(19) 1.13221(17) 0.81277(12) 0.0244(4) Uani 1 1 d . . . H13 H 0.5557 1.1321 0.8534 0.029 Uiso 1 1 calc R . . C25 C 0.3450(2) 1.1433(2) 0.87194(13) 0.0326(4) Uani 1 1 d . . . H10 H 0.3785 1.0607 0.9123 0.049 Uiso 1 1 calc R . . H11 H 0.2656 1.1431 0.8356 0.049 Uiso 1 1 calc R . . H12 H 0.3057 1.2332 0.9058 0.049 Uiso 1 1 calc R . . C26 C 0.4360(2) 1.26736(19) 0.75512(15) 0.0358(4) Uani 1 1 d . . . H14 H 0.3490 1.2820 0.7203 0.054 Uiso 1 1 calc R . . H15 H 0.5214 1.2545 0.7156 0.054 Uiso 1 1 calc R . . H16 H 0.4103 1.3518 0.7926 0.054 Uiso 1 1 calc R . . C27 C 0.47538(19) 0.98404(18) 0.64886(11) 0.0214(3) Uani 1 1 d . . . H17 H 0.4938 1.0593 0.6154 0.026 Uiso 1 1 calc R . . C28 C 0.3029(2) 1.0407(2) 0.65580(13) 0.0314(4) Uani 1 1 d . . . H21 H 0.2783 0.9671 0.6836 0.047 Uiso 1 1 calc R . . H22 H 0.2619 1.0620 0.5969 0.047 Uiso 1 1 calc R . . H23 H 0.2590 1.1289 0.6913 0.047 Uiso 1 1 calc R . . C29 C 0.5479(2) 0.8469(2) 0.59261(12) 0.0271(4) Uani 1 1 d . . . H18 H 0.5218 0.7728 0.6182 0.041 Uiso 1 1 calc R . . H19 H 0.6577 0.8110 0.5908 0.041 Uiso 1 1 calc R . . H20 H 0.5107 0.8691 0.5328 0.041 Uiso 1 1 calc R . . N1 N 0.75022(15) 0.91011(13) 0.73704(9) 0.0174(3) Uani 1 1 d . . . B1 B 0.8524(2) 0.75014(18) 0.77018(12) 0.0176(3) Uani 1 1 d . . . F1 F 0.78648(12) 0.98234(10) 0.91474(7) 0.0290(2) Uani 1 1 d . . . F2 F 0.92506(13) 0.94104(11) 1.06393(7) 0.0297(2) Uani 1 1 d . . . F3 F 1.14343(13) 0.67554(12) 1.10800(7) 0.0350(3) Uani 1 1 d . . . F4 F 1.21893(14) 0.45125(12) 0.99538(7) 0.0406(3) Uani 1 1 d . . . F5 F 1.08142(13) 0.48714(11) 0.84427(7) 0.0336(3) Uani 1 1 d . . . F6 F 1.11560(12) 0.80517(11) 0.73658(7) 0.0301(2) Uani 1 1 d . . . F7 F 1.34695(13) 0.66739(15) 0.62543(9) 0.0440(3) Uani 1 1 d . . . F8 F 1.36142(13) 0.44481(14) 0.52668(8) 0.0419(3) Uani 1 1 d . . . F9 F 1.13339(13) 0.36578(11) 0.54056(7) 0.0319(3) Uani 1 1 d . . . F10 F 0.89939(12) 0.50236(11) 0.64580(7) 0.0317(3) Uani 1 1 d . . . P1 P 0.56943(4) 0.96162(4) 0.75281(3) 0.01633(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0174(7) 0.0201(7) 0.0176(8) 0.0014(6) -0.0012(6) -0.0070(6) C2 0.0194(8) 0.0179(7) 0.0193(8) 0.0032(6) -0.0012(6) -0.0046(6) C3 0.0264(8) 0.0227(8) 0.0169(8) -0.0032(6) 0.0013(6) -0.0114(7) C4 0.0258(9) 0.0305(9) 0.0168(8) 0.0038(7) -0.0054(6) -0.0105(7) C5 0.0250(9) 0.0228(8) 0.0224(9) 0.0040(7) -0.0047(7) -0.0015(7) C6 0.0253(8) 0.0199(7) 0.0196(8) -0.0015(6) -0.0011(6) -0.0053(6) C7 0.0192(7) 0.0181(7) 0.0160(7) 0.0039(6) -0.0037(6) -0.0083(6) C8 0.0227(8) 0.0226(8) 0.0222(8) -0.0022(6) -0.0027(6) -0.0121(6) C9 0.0228(9) 0.0361(9) 0.0265(9) -0.0028(7) 0.0012(7) -0.0178(7) C10 0.0235(9) 0.0314(9) 0.0208(9) -0.0037(7) 0.0039(7) -0.0085(7) C11 0.0283(9) 0.0196(7) 0.0192(8) -0.0026(6) -0.0031(6) -0.0091(7) C12 0.0229(8) 0.0206(7) 0.0197(8) 0.0022(6) -0.0030(6) -0.0119(6) C13 0.0207(8) 0.0179(7) 0.0208(8) 0.0039(6) -0.0014(6) -0.0097(6) C14 0.0411(11) 0.0292(9) 0.0224(9) 0.0010(7) -0.0017(7) -0.0224(8) C15 0.0516(12) 0.0334(10) 0.0340(11) 0.0011(8) -0.0031(9) -0.0305(9) C16 0.0498(12) 0.0369(10) 0.0353(11) 0.0104(8) -0.0011(9) -0.0314(10) C17 0.0547(13) 0.0494(12) 0.0225(9) 0.0072(8) -0.0011(8) -0.0367(11) C18 0.0372(10) 0.0344(9) 0.0215(9) 0.0009(7) 0.0000(7) -0.0245(8) C19 0.0217(8) 0.0165(7) 0.0209(8) 0.0024(6) -0.0010(6) -0.0081(6) C20 0.0216(8) 0.0174(7) 0.0160(7) 0.0035(6) -0.0003(6) -0.0086(6) C21 0.0227(8) 0.0253(8) 0.0227(9) 0.0025(7) 0.0009(6) -0.0128(7) C22 0.0294(9) 0.0243(8) 0.0318(10) 0.0038(7) 0.0051(7) -0.0150(7) C23 0.0353(10) 0.0325(9) 0.0307(10) 0.0068(8) 0.0032(8) -0.0131(8) C24 0.0233(8) 0.0167(7) 0.0287(9) -0.0013(6) -0.0026(7) -0.0044(6) C25 0.0296(10) 0.0262(9) 0.0344(11) -0.0047(8) 0.0051(8) -0.0057(7) C26 0.0346(10) 0.0179(8) 0.0498(13) 0.0038(8) -0.0033(9) -0.0068(7) C27 0.0246(8) 0.0258(8) 0.0159(8) 0.0046(6) -0.0054(6) -0.0129(7) C28 0.0247(9) 0.0376(10) 0.0316(10) 0.0081(8) -0.0109(7) -0.0130(8) C29 0.0342(10) 0.0332(9) 0.0197(8) -0.0010(7) -0.0024(7) -0.0202(8) N1 0.0184(6) 0.0160(6) 0.0184(7) 0.0031(5) -0.0023(5) -0.0083(5) B1 0.0189(8) 0.0162(7) 0.0171(8) 0.0007(6) -0.0025(6) -0.0071(6) F1 0.0340(6) 0.0182(5) 0.0229(5) -0.0011(4) -0.0062(4) -0.0002(4) F2 0.0417(6) 0.0263(5) 0.0199(5) -0.0040(4) -0.0025(4) -0.0137(5) F3 0.0396(6) 0.0388(6) 0.0210(5) 0.0039(5) -0.0134(4) -0.0115(5) F4 0.0418(7) 0.0269(6) 0.0304(6) 0.0030(5) -0.0137(5) 0.0063(5) F5 0.0425(7) 0.0198(5) 0.0231(5) -0.0014(4) -0.0071(5) 0.0008(4) F6 0.0294(6) 0.0352(6) 0.0338(6) -0.0121(5) 0.0027(4) -0.0214(5) F7 0.0334(6) 0.0634(8) 0.0496(8) -0.0204(6) 0.0143(5) -0.0349(6) F8 0.0315(6) 0.0516(7) 0.0408(7) -0.0197(6) 0.0164(5) -0.0174(5) F9 0.0378(6) 0.0269(5) 0.0315(6) -0.0127(4) 0.0048(5) -0.0147(5) F10 0.0335(6) 0.0316(5) 0.0396(6) -0.0143(5) 0.0100(5) -0.0234(5) P1 0.0177(2) 0.01517(19) 0.0157(2) 0.00232(14) -0.00207(15) -0.00675(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.376(2) . ? C1 C6 1.398(2) . ? C1 B1 1.673(2) . ? C2 F1 1.3575(18) . ? C2 C3 1.385(2) . ? C3 F2 1.3431(19) . ? C3 C4 1.375(2) . ? C4 F3 1.3397(19) . ? C4 C5 1.373(2) . ? C5 F4 1.3463(19) . ? C5 C6 1.379(2) . ? C6 F5 1.3618(19) . ? C7 C12 1.391(2) . ? C7 C8 1.392(2) . ? C7 B1 1.647(2) . ? C8 F6 1.3529(18) . ? C8 C9 1.380(2) . ? C9 F7 1.3417(19) . ? C9 C10 1.370(2) . ? C10 F8 1.339(2) . ? C10 C11 1.370(2) . ? C11 F9 1.3465(18) . ? C11 C12 1.379(2) . ? C12 F10 1.3490(18) . ? C13 C18 1.381(2) . ? C13 C14 1.389(2) . ? C13 N1 1.4438(19) . ? C14 C15 1.387(2) . ? C14 H28 0.9500 . ? C15 C16 1.374(3) . ? C15 H29 0.9500 . ? C16 C17 1.380(3) . ? C16 H2 0.9500 . ? C17 C18 1.386(2) . ? C17 H26 0.9500 . ? C18 H27 0.9500 . ? C19 C20 1.545(2) . ? C19 B1 1.634(2) . ? C19 H24 0.9900 . ? C19 H25 0.9900 . ? C20 C21 1.538(2) . ? C20 P1 1.8149(15) . ? C20 H3 1.0000 . ? C21 C22 1.527(2) . ? C21 H8 0.9900 . ? C21 H9 0.9900 . ? C22 C23 1.509(3) . ? C22 H4 0.9900 . ? C22 H7 0.9900 . ? C23 H1 0.9800 . ? C23 H5 0.9800 . ? C23 H6 0.9800 . ? C24 C25 1.534(3) . ? C24 C26 1.536(2) . ? C24 P1 1.8267(17) . ? C24 H13 1.0000 . ? C25 H10 0.9800 . ? C25 H11 0.9800 . ? C25 H12 0.9800 . ? C26 H14 0.9800 . ? C26 H15 0.9800 . ? C26 H16 0.9800 . ? C27 C29 1.533(2) . ? C27 C28 1.540(2) . ? C27 P1 1.8264(17) . ? C27 H17 1.0000 . ? C28 H21 0.9800 . ? C28 H22 0.9800 . ? C28 H23 0.9800 . ? C29 H18 0.9800 . ? C29 H19 0.9800 . ? C29 H20 0.9800 . ? N1 B1 1.592(2) . ? N1 P1 1.6352(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 112.36(14) . . ? C2 C1 B1 128.45(14) . . ? C6 C1 B1 119.06(14) . . ? F1 C2 C1 120.87(14) . . ? F1 C2 C3 113.98(14) . . ? C1 C2 C3 125.14(15) . . ? F2 C3 C4 119.53(15) . . ? F2 C3 C2 120.93(15) . . ? C4 C3 C2 119.53(15) . . ? F3 C4 C5 120.54(15) . . ? F3 C4 C3 120.99(16) . . ? C5 C4 C3 118.47(15) . . ? F4 C5 C4 119.42(15) . . ? F4 C5 C6 120.93(15) . . ? C4 C5 C6 119.64(15) . . ? F5 C6 C5 115.34(14) . . ? F5 C6 C1 119.83(14) . . ? C5 C6 C1 124.81(15) . . ? C12 C7 C8 112.68(14) . . ? C12 C7 B1 126.05(14) . . ? C8 C7 B1 121.17(14) . . ? F6 C8 C9 115.59(14) . . ? F6 C8 C7 119.84(15) . . ? C9 C8 C7 124.55(15) . . ? F7 C9 C10 119.31(16) . . ? F7 C9 C8 120.89(15) . . ? C10 C9 C8 119.80(15) . . ? F8 C10 C11 120.53(16) . . ? F8 C10 C9 120.92(16) . . ? C11 C10 C9 118.54(16) . . ? F9 C11 C10 119.74(15) . . ? F9 C11 C12 120.24(15) . . ? C10 C11 C12 120.02(15) . . ? F10 C12 C11 114.38(14) . . ? F10 C12 C7 121.20(14) . . ? C11 C12 C7 124.40(15) . . ? C18 C13 C14 118.48(15) . . ? C18 C13 N1 120.11(14) . . ? C14 C13 N1 121.39(15) . . ? C15 C14 C13 120.47(17) . . ? C15 C14 H28 119.8 . . ? C13 C14 H28 119.8 . . ? C16 C15 C14 120.64(17) . . ? C16 C15 H29 119.7 . . ? C14 C15 H29 119.7 . . ? C15 C16 C17 119.19(17) . . ? C15 C16 H2 120.4 . . ? C17 C16 H2 120.4 . . ? C16 C17 C18 120.39(18) . . ? C16 C17 H26 119.8 . . ? C18 C17 H26 119.8 . . ? C13 C18 C17 120.78(16) . . ? C13 C18 H27 119.6 . . ? C17 C18 H27 119.6 . . ? C20 C19 B1 108.31(12) . . ? C20 C19 H24 110.0 . . ? B1 C19 H24 110.0 . . ? C20 C19 H25 110.0 . . ? B1 C19 H25 110.0 . . ? H24 C19 H25 108.4 . . ? C21 C20 C19 115.06(13) . . ? C21 C20 P1 115.94(11) . . ? C19 C20 P1 101.95(10) . . ? C21 C20 H3 107.8 . . ? C19 C20 H3 107.8 . . ? P1 C20 H3 107.8 . . ? C22 C21 C20 113.60(14) . . ? C22 C21 H8 108.8 . . ? C20 C21 H8 108.8 . . ? C22 C21 H9 108.8 . . ? C20 C21 H9 108.8 . . ? H8 C21 H9 107.7 . . ? C23 C22 C21 112.89(15) . . ? C23 C22 H4 109.0 . . ? C21 C22 H4 109.0 . . ? C23 C22 H7 109.0 . . ? C21 C22 H7 109.0 . . ? H4 C22 H7 107.8 . . ? C22 C23 H1 109.5 . . ? C22 C23 H5 109.5 . . ? H1 C23 H5 109.5 . . ? C22 C23 H6 109.5 . . ? H1 C23 H6 109.5 . . ? H5 C23 H6 109.5 . . ? C25 C24 C26 111.45(15) . . ? C25 C24 P1 112.96(12) . . ? C26 C24 P1 114.41(13) . . ? C25 C24 H13 105.7 . . ? C26 C24 H13 105.7 . . ? P1 C24 H13 105.7 . . ? C24 C25 H10 109.5 . . ? C24 C25 H11 109.5 . . ? H10 C25 H11 109.5 . . ? C24 C25 H12 109.5 . . ? H10 C25 H12 109.5 . . ? H11 C25 H12 109.5 . . ? C24 C26 H14 109.5 . . ? C24 C26 H15 109.5 . . ? H14 C26 H15 109.5 . . ? C24 C26 H16 109.5 . . ? H14 C26 H16 109.5 . . ? H15 C26 H16 109.5 . . ? C29 C27 C28 110.92(14) . . ? C29 C27 P1 111.81(12) . . ? C28 C27 P1 115.77(12) . . ? C29 C27 H17 105.8 . . ? C28 C27 H17 105.8 . . ? P1 C27 H17 105.8 . . ? C27 C28 H21 109.5 . . ? C27 C28 H22 109.5 . . ? H21 C28 H22 109.5 . . ? C27 C28 H23 109.5 . . ? H21 C28 H23 109.5 . . ? H22 C28 H23 109.5 . . ? C27 C29 H18 109.5 . . ? C27 C29 H19 109.5 . . ? H18 C29 H19 109.5 . . ? C27 C29 H20 109.5 . . ? H18 C29 H20 109.5 . . ? H19 C29 H20 109.5 . . ? C13 N1 B1 127.56(13) . . ? C13 N1 P1 118.51(10) . . ? B1 N1 P1 113.77(10) . . ? N1 B1 C19 101.88(12) . . ? N1 B1 C7 109.70(12) . . ? C19 B1 C7 116.64(13) . . ? N1 B1 C1 114.74(12) . . ? C19 B1 C1 106.91(13) . . ? C7 B1 C1 107.19(12) . . ? N1 P1 C20 98.42(7) . . ? N1 P1 C27 111.42(7) . . ? C20 P1 C27 115.07(8) . . ? N1 P1 C24 111.74(7) . . ? C20 P1 C24 111.80(8) . . ? C27 P1 C24 108.22(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 F1 -176.18(14) . . . . ? B1 C1 C2 F1 -0.3(3) . . . . ? C6 C1 C2 C3 2.5(2) . . . . ? B1 C1 C2 C3 178.35(15) . . . . ? F1 C2 C3 F2 -1.9(2) . . . . ? C1 C2 C3 F2 179.37(15) . . . . ? F1 C2 C3 C4 177.73(15) . . . . ? C1 C2 C3 C4 -1.0(3) . . . . ? F2 C3 C4 F3 -0.2(3) . . . . ? C2 C3 C4 F3 -179.80(15) . . . . ? F2 C3 C4 C5 178.95(15) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? F3 C4 C5 F4 0.1(3) . . . . ? C3 C4 C5 F4 -179.04(16) . . . . ? F3 C4 C5 C6 179.73(16) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? F4 C5 C6 F5 2.3(3) . . . . ? C4 C5 C6 F5 -177.31(16) . . . . ? F4 C5 C6 C1 -179.23(17) . . . . ? C4 C5 C6 C1 1.1(3) . . . . ? C2 C1 C6 F5 175.83(14) . . . . ? B1 C1 C6 F5 -0.5(2) . . . . ? C2 C1 C6 C5 -2.5(3) . . . . ? B1 C1 C6 C5 -178.84(16) . . . . ? C12 C7 C8 F6 -178.19(14) . . . . ? B1 C7 C8 F6 -1.5(2) . . . . ? C12 C7 C8 C9 0.0(2) . . . . ? B1 C7 C8 C9 176.72(16) . . . . ? F6 C8 C9 F7 -1.7(3) . . . . ? C7 C8 C9 F7 -179.92(16) . . . . ? F6 C8 C9 C10 177.85(16) . . . . ? C7 C8 C9 C10 -0.4(3) . . . . ? F7 C9 C10 F8 0.3(3) . . . . ? C8 C9 C10 F8 -179.18(16) . . . . ? F7 C9 C10 C11 179.65(16) . . . . ? C8 C9 C10 C11 0.1(3) . . . . ? F8 C10 C11 F9 0.5(3) . . . . ? C9 C10 C11 F9 -178.82(16) . . . . ? F8 C10 C11 C12 179.86(16) . . . . ? C9 C10 C11 C12 0.5(3) . . . . ? F9 C11 C12 F10 -0.2(2) . . . . ? C10 C11 C12 F10 -179.61(15) . . . . ? F9 C11 C12 C7 178.34(15) . . . . ? C10 C11 C12 C7 -1.0(3) . . . . ? C8 C7 C12 F10 179.21(14) . . . . ? B1 C7 C12 F10 2.7(2) . . . . ? C8 C7 C12 C11 0.7(2) . . . . ? B1 C7 C12 C11 -175.81(15) . . . . ? C18 C13 C14 C15 1.6(3) . . . . ? N1 C13 C14 C15 -176.61(17) . . . . ? C13 C14 C15 C16 0.2(3) . . . . ? C14 C15 C16 C17 -1.2(3) . . . . ? C15 C16 C17 C18 0.4(3) . . . . ? C14 C13 C18 C17 -2.5(3) . . . . ? N1 C13 C18 C17 175.80(18) . . . . ? C16 C17 C18 C13 1.5(3) . . . . ? B1 C19 C20 C21 167.04(13) . . . . ? B1 C19 C20 P1 40.70(14) . . . . ? C19 C20 C21 C22 67.75(19) . . . . ? P1 C20 C21 C22 -173.45(12) . . . . ? C20 C21 C22 C23 72.92(19) . . . . ? C18 C13 N1 B1 91.4(2) . . . . ? C14 C13 N1 B1 -90.4(2) . . . . ? C18 C13 N1 P1 -83.59(18) . . . . ? C14 C13 N1 P1 94.62(17) . . . . ? C13 N1 B1 C19 -161.56(14) . . . . ? P1 N1 B1 C19 13.62(14) . . . . ? C13 N1 B1 C7 -37.4(2) . . . . ? P1 N1 B1 C7 137.81(11) . . . . ? C13 N1 B1 C1 83.34(19) . . . . ? P1 N1 B1 C1 -101.48(13) . . . . ? C20 C19 B1 N1 -35.28(15) . . . . ? C20 C19 B1 C7 -154.69(13) . . . . ? C20 C19 B1 C1 85.44(15) . . . . ? C12 C7 B1 N1 -110.64(17) . . . . ? C8 C7 B1 N1 73.10(18) . . . . ? C12 C7 B1 C19 4.5(2) . . . . ? C8 C7 B1 C19 -171.79(14) . . . . ? C12 C7 B1 C1 124.18(16) . . . . ? C8 C7 B1 C1 -52.07(18) . . . . ? C2 C1 B1 N1 14.3(2) . . . . ? C6 C1 B1 N1 -170.11(14) . . . . ? C2 C1 B1 C19 -97.89(18) . . . . ? C6 C1 B1 C19 77.74(18) . . . . ? C2 C1 B1 C7 136.34(16) . . . . ? C6 C1 B1 C7 -48.03(18) . . . . ? C13 N1 P1 C20 -175.48(12) . . . . ? B1 N1 P1 C20 8.87(12) . . . . ? C13 N1 P1 C27 63.31(13) . . . . ? B1 N1 P1 C27 -112.34(11) . . . . ? C13 N1 P1 C24 -57.89(14) . . . . ? B1 N1 P1 C24 126.46(11) . . . . ? C21 C20 P1 N1 -155.12(12) . . . . ? C19 C20 P1 N1 -29.35(11) . . . . ? C21 C20 P1 C27 -36.64(15) . . . . ? C19 C20 P1 C27 89.13(12) . . . . ? C21 C20 P1 C24 87.33(13) . . . . ? C19 C20 P1 C24 -146.90(10) . . . . ? C29 C27 P1 N1 54.94(13) . . . . ? C28 C27 P1 N1 -176.72(12) . . . . ? C29 C27 P1 C20 -55.99(14) . . . . ? C28 C27 P1 C20 72.35(14) . . . . ? C29 C27 P1 C24 178.17(11) . . . . ? C28 C27 P1 C24 -53.49(14) . . . . ? C25 C24 P1 N1 -147.81(13) . . . . ? C26 C24 P1 N1 83.26(14) . . . . ? C25 C24 P1 C20 -38.58(15) . . . . ? C26 C24 P1 C20 -167.51(13) . . . . ? C25 C24 P1 C27 89.15(14) . . . . ? C26 C24 P1 C27 -39.78(15) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.480 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.064 data_cj049_0m _database_code_depnum_ccdc_archive 'CCDC 910003' #TrackingRef 'CIFs-revised.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H33 B F10 N P' _chemical_formula_weight 651.36 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.9145(4) _cell_length_b 19.2534(11) _cell_length_c 17.0916(9) _cell_angle_alpha 90.00 _cell_angle_beta 99.678(2) _cell_angle_gamma 90.00 _cell_volume 2891.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9946 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 27.47 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.184 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9642 _exptl_absorpt_correction_T_max 0.9909 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25061 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 27.52 _reflns_number_total 6624 _reflns_number_gt 5127 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0459P)^2^+1.0574P] 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 6624 _refine_ls_number_parameters 404 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0974 _refine_ls_wR_factor_gt 0.0883 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 P1 P 0.29316(4) 0.80790(2) 0.20752(2) 0.01587(10) Uani 1 1 d . . . F1 F 0.83206(10) 0.67267(5) 0.26773(6) 0.0288(2) Uani 1 1 d . . . F2 F 0.79249(12) 0.55106(5) 0.49977(6) 0.0350(3) Uani 1 1 d . . . F3 F 0.48749(12) 0.57845(5) 0.47743(6) 0.0330(2) Uani 1 1 d . . . F4 F 0.35378(10) 0.64755(5) 0.35179(6) 0.0298(2) Uani 1 1 d . . . F5 F 0.96127(11) 0.59899(6) 0.39199(6) 0.0375(3) Uani 1 1 d . . . F6 F 0.63519(11) 0.78591(5) 0.08351(5) 0.0265(2) Uani 1 1 d . . . F7 F 0.73372(12) 0.72617(6) -0.03662(6) 0.0375(3) Uani 1 1 d . . . F8 F 0.73658(14) 0.58508(6) -0.05086(6) 0.0457(3) Uani 1 1 d . . . F9 F 0.63979(13) 0.50508(5) 0.06290(6) 0.0402(3) Uani 1 1 d . . . F10 F 0.54287(12) 0.56258(5) 0.18535(6) 0.0302(2) Uani 1 1 d . . . N1 N 0.34388(13) 0.72564(6) 0.20152(7) 0.0158(3) Uani 1 1 d . . . C17 C 0.05453(19) 0.56133(9) 0.09846(11) 0.0283(4) Uani 1 1 d . . . H1 H -0.0091 0.5246 0.0753 0.034 Uiso 1 1 calc R . . C18 C 0.04280(18) 0.58596(9) 0.17294(10) 0.0262(4) Uani 1 1 d . . . H11 H -0.0301 0.5663 0.2011 0.031 Uiso 1 1 calc R . . C19 C 0.13660(17) 0.63943(8) 0.20734(10) 0.0212(3) Uani 1 1 d . . . H8 H 0.1284 0.6550 0.2592 0.025 Uiso 1 1 calc R . . C14 C 0.24184(16) 0.67043(8) 0.16705(9) 0.0168(3) Uani 1 1 d . . . C2 C 0.48040(17) 0.84845(8) 0.21052(9) 0.0188(3) Uani 1 1 d . . . H32 H 0.4942 0.8535 0.1539 0.023 Uiso 1 1 calc R . . C3 C 0.51145(18) 0.92115(8) 0.24816(10) 0.0233(3) Uani 1 1 d . . . H7 H 0.4395 0.9548 0.2184 0.028 Uiso 1 1 calc R . . H33 H 0.4916 0.9197 0.3034 0.028 Uiso 1 1 calc R . . C4 C 0.67443(18) 0.94682(9) 0.24873(10) 0.0259(4) Uani 1 1 d . . . H6 H 0.6883 0.9916 0.2776 0.031 Uiso 1 1 calc R . . H5 H 0.7463 0.9130 0.2782 0.031 Uiso 1 1 calc R . . C5 C 0.7140(2) 0.95669(10) 0.16689(11) 0.0327(4) Uani 1 1 d . . . H3 H 0.7154 0.9115 0.1407 0.049 Uiso 1 1 calc R . . H2 H 0.8146 0.9784 0.1714 0.049 Uiso 1 1 calc R . . H4 H 0.6378 0.9866 0.1354 0.049 Uiso 1 1 calc R . . C1 C 0.59244(17) 0.79136(8) 0.24599(9) 0.0184(3) Uani 1 1 d . . . H31 H 0.6130 0.7960 0.3045 0.022 Uiso 1 1 calc R . . H30 H 0.6899 0.7974 0.2263 0.022 Uiso 1 1 calc R . . C26 C 0.58441(17) 0.66369(8) 0.30050(9) 0.0178(3) Uani 1 1 d . . . C31 C 0.73937(17) 0.64907(8) 0.31752(9) 0.0208(3) Uani 1 1 d . . . C30 C 0.80999(18) 0.61151(9) 0.38168(10) 0.0240(4) Uani 1 1 d . . . C29 C 0.72546(19) 0.58712(9) 0.43598(9) 0.0245(4) Uani 1 1 d . . . C28 C 0.57226(19) 0.60083(8) 0.42413(9) 0.0228(3) Uani 1 1 d . . . C27 C 0.50617(17) 0.63757(8) 0.35754(9) 0.0201(3) Uani 1 1 d . . . C16 C 0.16044(19) 0.59097(9) 0.05794(10) 0.0270(4) Uani 1 1 d . . . H10 H 0.1707 0.5741 0.0069 0.032 Uiso 1 1 calc R . . C15 C 0.25168(18) 0.64514(8) 0.09159(9) 0.0219(3) Uani 1 1 d . . . H9 H 0.3225 0.6655 0.0626 0.026 Uiso 1 1 calc R . . C6 C 0.21295(18) 0.82957(9) 0.29976(10) 0.0227(3) Uani 1 1 d . . . C8 C 0.1570(2) 0.90531(9) 0.29971(11) 0.0313(4) Uani 1 1 d . . . H12 H 0.0642 0.9105 0.2603 0.047 Uiso 1 1 calc R . . H13 H 0.2359 0.9364 0.2863 0.047 Uiso 1 1 calc R . . H14 H 0.1352 0.9171 0.3524 0.047 Uiso 1 1 calc R . . C9 C 0.0801(2) 0.78189(10) 0.31214(11) 0.0328(4) Uani 1 1 d . . . H16 H 0.1192 0.7354 0.3274 0.049 Uiso 1 1 calc R . . H17 H 0.0066 0.7790 0.2627 0.049 Uiso 1 1 calc R . . H15 H 0.0299 0.8010 0.3542 0.049 Uiso 1 1 calc R . . C7 C 0.3393(2) 0.81827(10) 0.37225(10) 0.0295(4) Uani 1 1 d . . . H19 H 0.2961 0.8227 0.4211 0.044 Uiso 1 1 calc R . . H18 H 0.4192 0.8532 0.3721 0.044 Uiso 1 1 calc R . . H20 H 0.3828 0.7718 0.3696 0.044 Uiso 1 1 calc R . . C10 C 0.16572(18) 0.83808(8) 0.11537(10) 0.0230(3) Uani 1 1 d . . . C12 C -0.00017(19) 0.81410(10) 0.11229(12) 0.0330(4) Uani 1 1 d . . . H22 H -0.0446 0.8384 0.1533 0.049 Uiso 1 1 calc R . . H21 H -0.0022 0.7639 0.1216 0.049 Uiso 1 1 calc R . . H23 H -0.0592 0.8248 0.0600 0.049 Uiso 1 1 calc R . . C13 C 0.1709(2) 0.91778(9) 0.10856(11) 0.0321(4) Uani 1 1 d . . . H25 H 0.1034 0.9327 0.0602 0.048 Uiso 1 1 calc R . . H24 H 0.2752 0.9326 0.1062 0.048 Uiso 1 1 calc R . . H26 H 0.1373 0.9388 0.1549 0.048 Uiso 1 1 calc R . . C11 C 0.2248(2) 0.80890(10) 0.04254(10) 0.0305(4) Uani 1 1 d . . . H27 H 0.1966 0.7598 0.0357 0.046 Uiso 1 1 calc R . . H29 H 0.3358 0.8134 0.0504 0.046 Uiso 1 1 calc R . . H28 H 0.1796 0.8349 -0.0049 0.046 Uiso 1 1 calc R . . C20 C 0.58600(16) 0.67824(8) 0.14400(9) 0.0177(3) Uani 1 1 d . . . C25 C 0.59134(18) 0.60685(8) 0.13261(9) 0.0221(3) Uani 1 1 d . . . C24 C 0.6395(2) 0.57485(9) 0.06919(10) 0.0263(4) Uani 1 1 d . . . C23 C 0.6879(2) 0.61481(10) 0.01151(9) 0.0291(4) Uani 1 1 d . . . C22 C 0.68659(18) 0.68577(9) 0.01892(9) 0.0243(4) Uani 1 1 d . . . C21 C 0.63586(17) 0.71525(8) 0.08354(9) 0.0195(3) Uani 1 1 d . . . B1 B 0.52433(18) 0.71372(9) 0.22212(10) 0.0166(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 P1 0.01440(18) 0.0146(2) 0.0187(2) -0.00200(15) 0.00298(14) -0.00012(16) F1 0.0168(5) 0.0388(6) 0.0317(5) 0.0026(4) 0.0072(4) -0.0014(4) F2 0.0440(6) 0.0348(6) 0.0221(5) 0.0038(4) -0.0059(4) 0.0119(5) F3 0.0399(6) 0.0362(6) 0.0246(5) 0.0086(4) 0.0103(4) 0.0001(5) F4 0.0184(5) 0.0406(6) 0.0319(5) 0.0114(4) 0.0081(4) 0.0024(4) F5 0.0210(5) 0.0507(7) 0.0376(6) -0.0005(5) -0.0043(4) 0.0109(5) F6 0.0352(5) 0.0183(5) 0.0286(5) 0.0024(4) 0.0130(4) -0.0010(4) F7 0.0501(7) 0.0427(7) 0.0237(5) 0.0048(5) 0.0175(5) 0.0008(5) F8 0.0692(8) 0.0459(7) 0.0243(6) -0.0085(5) 0.0146(5) 0.0189(6) F9 0.0654(8) 0.0197(5) 0.0334(6) -0.0069(4) 0.0022(5) 0.0123(5) F10 0.0477(6) 0.0161(5) 0.0283(5) 0.0034(4) 0.0105(4) -0.0013(4) N1 0.0150(6) 0.0144(6) 0.0178(6) -0.0020(5) 0.0022(5) -0.0014(5) C17 0.0253(9) 0.0203(9) 0.0375(10) -0.0079(7) -0.0002(7) -0.0058(7) C18 0.0207(8) 0.0222(9) 0.0370(10) -0.0013(7) 0.0084(7) -0.0059(7) C19 0.0186(8) 0.0205(8) 0.0253(8) -0.0022(7) 0.0064(6) -0.0002(7) C14 0.0155(7) 0.0131(7) 0.0209(8) -0.0009(6) 0.0001(6) 0.0010(6) C2 0.0173(7) 0.0165(8) 0.0234(8) -0.0025(6) 0.0059(6) -0.0023(6) C3 0.0220(8) 0.0185(8) 0.0296(9) -0.0057(7) 0.0047(6) -0.0033(7) C4 0.0255(9) 0.0211(9) 0.0307(9) -0.0056(7) 0.0038(7) -0.0049(7) C5 0.0342(10) 0.0283(10) 0.0375(10) 0.0015(8) 0.0111(8) -0.0019(8) C1 0.0161(7) 0.0191(8) 0.0200(8) -0.0007(6) 0.0027(6) -0.0006(6) C26 0.0191(8) 0.0143(7) 0.0198(8) -0.0024(6) 0.0027(6) -0.0012(6) C31 0.0206(8) 0.0202(8) 0.0219(8) -0.0033(6) 0.0045(6) -0.0009(7) C30 0.0188(8) 0.0241(9) 0.0268(9) -0.0061(7) -0.0026(6) 0.0041(7) C29 0.0314(9) 0.0203(9) 0.0189(8) -0.0015(6) -0.0042(7) 0.0045(7) C28 0.0301(9) 0.0205(8) 0.0184(8) -0.0016(6) 0.0053(6) -0.0019(7) C27 0.0167(7) 0.0197(8) 0.0237(8) -0.0009(6) 0.0029(6) 0.0012(6) C16 0.0295(9) 0.0259(9) 0.0248(9) -0.0096(7) 0.0026(7) -0.0022(7) C15 0.0209(8) 0.0219(8) 0.0228(8) -0.0007(6) 0.0036(6) -0.0011(7) C6 0.0216(8) 0.0220(8) 0.0267(9) -0.0072(7) 0.0108(6) -0.0005(7) C8 0.0306(9) 0.0262(10) 0.0386(10) -0.0117(8) 0.0103(8) 0.0020(8) C9 0.0322(10) 0.0329(10) 0.0383(10) -0.0096(8) 0.0203(8) -0.0069(8) C7 0.0355(10) 0.0339(10) 0.0208(8) -0.0050(7) 0.0092(7) 0.0001(8) C10 0.0213(8) 0.0194(8) 0.0262(8) 0.0023(7) -0.0021(6) 0.0008(7) C12 0.0209(8) 0.0316(10) 0.0421(11) 0.0030(8) -0.0069(7) -0.0015(8) C13 0.0358(10) 0.0204(9) 0.0367(10) 0.0050(8) -0.0036(8) 0.0021(8) C11 0.0401(10) 0.0290(10) 0.0200(8) 0.0031(7) -0.0018(7) 0.0025(8) C20 0.0149(7) 0.0179(8) 0.0200(8) -0.0012(6) 0.0023(6) 0.0016(6) C25 0.0238(8) 0.0209(9) 0.0208(8) 0.0019(6) 0.0011(6) 0.0011(7) C24 0.0346(9) 0.0181(9) 0.0238(9) -0.0043(7) -0.0020(7) 0.0092(7) C23 0.0351(10) 0.0340(10) 0.0175(8) -0.0064(7) 0.0024(7) 0.0120(8) C22 0.0259(8) 0.0301(10) 0.0175(8) 0.0041(7) 0.0052(6) 0.0008(7) C21 0.0177(8) 0.0184(8) 0.0222(8) -0.0009(6) 0.0031(6) 0.0014(6) B1 0.0141(8) 0.0169(9) 0.0191(8) 0.0006(7) 0.0038(6) 0.0005(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 P1 N1 1.6549(13) . ? P1 C2 1.8357(15) . ? P1 C10 1.8728(16) . ? P1 C6 1.8840(16) . ? F1 C31 1.3600(18) . ? F2 C29 1.3449(18) . ? F3 C28 1.3484(18) . ? F4 C27 1.3592(17) . ? F5 C30 1.3520(18) . ? F6 C21 1.3604(19) . ? F7 C22 1.3479(18) . ? F8 C23 1.3445(19) . ? F9 C24 1.3476(19) . ? F10 C25 1.3625(18) . ? N1 C14 1.4575(19) . ? N1 B1 1.604(2) . ? C17 C18 1.379(2) . ? C17 C16 1.384(2) . ? C17 H1 0.9500 . ? C18 C19 1.393(2) . ? C18 H11 0.9500 . ? C19 C14 1.388(2) . ? C19 H8 0.9500 . ? C14 C15 1.395(2) . ? C2 C1 1.539(2) . ? C2 C3 1.546(2) . ? C2 H32 1.0000 . ? C3 C4 1.533(2) . ? C3 H7 0.9900 . ? C3 H33 0.9900 . ? C4 C5 1.511(2) . ? C4 H6 0.9900 . ? C4 H5 0.9900 . ? C5 H3 0.9800 . ? C5 H2 0.9800 . ? C5 H4 0.9800 . ? C1 B1 1.639(2) . ? C1 H31 0.9900 . ? C1 H30 0.9900 . ? C26 C27 1.385(2) . ? C26 C31 1.392(2) . ? C26 B1 1.664(2) . ? C31 C30 1.375(2) . ? C30 C29 1.373(2) . ? C29 C28 1.372(2) . ? C28 C27 1.385(2) . ? C16 C15 1.387(2) . ? C16 H10 0.9500 . ? C15 H9 0.9500 . ? C6 C9 1.541(2) . ? C6 C8 1.541(2) . ? C6 C7 1.543(2) . ? C8 H12 0.9800 . ? C8 H13 0.9800 . ? C8 H14 0.9800 . ? C9 H16 0.9800 . ? C9 H17 0.9800 . ? C9 H15 0.9800 . ? C7 H19 0.9800 . ? C7 H18 0.9800 . ? C7 H20 0.9800 . ? C10 C11 1.537(2) . ? C10 C13 1.540(2) . ? C10 C12 1.542(2) . ? C12 H22 0.9800 . ? C12 H21 0.9800 . ? C12 H23 0.9800 . ? C13 H25 0.9800 . ? C13 H24 0.9800 . ? C13 H26 0.9800 . ? C11 H27 0.9800 . ? C11 H29 0.9800 . ? C11 H28 0.9800 . ? C20 C21 1.388(2) . ? C20 C25 1.390(2) . ? C20 B1 1.673(2) . ? C25 C24 1.377(2) . ? C24 C23 1.376(3) . ? C23 C22 1.372(3) . ? C22 C21 1.384(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 P1 C2 98.75(7) . . ? N1 P1 C10 112.22(7) . . ? C2 P1 C10 108.16(7) . . ? N1 P1 C6 114.20(7) . . ? C2 P1 C6 110.71(7) . . ? C10 P1 C6 111.91(7) . . ? C14 N1 B1 121.26(12) . . ? C14 N1 P1 124.38(10) . . ? B1 N1 P1 113.43(10) . . ? C18 C17 C16 118.95(15) . . ? C18 C17 H1 120.5 . . ? C16 C17 H1 120.5 . . ? C17 C18 C19 120.71(15) . . ? C17 C18 H11 119.6 . . ? C19 C18 H11 119.6 . . ? C14 C19 C18 121.08(15) . . ? C14 C19 H8 119.5 . . ? C18 C19 H8 119.5 . . ? C19 C14 C15 117.47(14) . . ? C19 C14 N1 122.74(13) . . ? C15 C14 N1 119.75(13) . . ? C1 C2 C3 115.07(13) . . ? C1 C2 P1 103.53(10) . . ? C3 C2 P1 119.68(11) . . ? C1 C2 H32 105.8 . . ? C3 C2 H32 105.8 . . ? P1 C2 H32 105.8 . . ? C4 C3 C2 113.43(13) . . ? C4 C3 H7 108.9 . . ? C2 C3 H7 108.9 . . ? C4 C3 H33 108.9 . . ? C2 C3 H33 108.9 . . ? H7 C3 H33 107.7 . . ? C5 C4 C3 113.78(14) . . ? C5 C4 H6 108.8 . . ? C3 C4 H6 108.8 . . ? C5 C4 H5 108.8 . . ? C3 C4 H5 108.8 . . ? H6 C4 H5 107.7 . . ? C4 C5 H3 109.5 . . ? C4 C5 H2 109.5 . . ? H3 C5 H2 109.5 . . ? C4 C5 H4 109.5 . . ? H3 C5 H4 109.5 . . ? H2 C5 H4 109.5 . . ? C2 C1 B1 111.38(12) . . ? C2 C1 H31 109.4 . . ? B1 C1 H31 109.4 . . ? C2 C1 H30 109.4 . . ? B1 C1 H30 109.4 . . ? H31 C1 H30 108.0 . . ? C27 C26 C31 112.27(14) . . ? C27 C26 B1 130.16(13) . . ? C31 C26 B1 117.33(13) . . ? F1 C31 C30 115.47(14) . . ? F1 C31 C26 119.19(14) . . ? C30 C31 C26 125.34(15) . . ? F5 C30 C29 119.98(14) . . ? F5 C30 C31 120.71(15) . . ? C29 C30 C31 119.30(15) . . ? F2 C29 C28 120.96(15) . . ? F2 C29 C30 120.34(15) . . ? C28 C29 C30 118.70(15) . . ? F3 C28 C29 119.72(14) . . ? F3 C28 C27 120.61(14) . . ? C29 C28 C27 119.67(15) . . ? F4 C27 C28 114.44(14) . . ? F4 C27 C26 120.87(13) . . ? C28 C27 C26 124.68(14) . . ? C17 C16 C15 120.29(16) . . ? C17 C16 H10 119.9 . . ? C15 C16 H10 119.9 . . ? C16 C15 C14 121.48(15) . . ? C16 C15 H9 119.3 . . ? C14 C15 H9 119.3 . . ? C9 C6 C8 107.90(14) . . ? C9 C6 C7 106.25(14) . . ? C8 C6 C7 109.05(14) . . ? C9 C6 P1 113.05(11) . . ? C8 C6 P1 112.18(12) . . ? C7 C6 P1 108.19(11) . . ? C6 C8 H12 109.5 . . ? C6 C8 H13 109.5 . . ? H12 C8 H13 109.5 . . ? C6 C8 H14 109.5 . . ? H12 C8 H14 109.5 . . ? H13 C8 H14 109.5 . . ? C6 C9 H16 109.5 . . ? C6 C9 H17 109.5 . . ? H16 C9 H17 109.5 . . ? C6 C9 H15 109.5 . . ? H16 C9 H15 109.5 . . ? H17 C9 H15 109.5 . . ? C6 C7 H19 109.5 . . ? C6 C7 H18 109.5 . . ? H19 C7 H18 109.5 . . ? C6 C7 H20 109.5 . . ? H19 C7 H20 109.5 . . ? H18 C7 H20 109.5 . . ? C11 C10 C13 106.52(14) . . ? C11 C10 C12 108.68(14) . . ? C13 C10 C12 109.65(14) . . ? C11 C10 P1 109.01(11) . . ? C13 C10 P1 110.56(11) . . ? C12 C10 P1 112.24(12) . . ? C10 C12 H22 109.5 . . ? C10 C12 H21 109.5 . . ? H22 C12 H21 109.5 . . ? C10 C12 H23 109.5 . . ? H22 C12 H23 109.5 . . ? H21 C12 H23 109.5 . . ? C10 C13 H25 109.5 . . ? C10 C13 H24 109.5 . . ? H25 C13 H24 109.5 . . ? C10 C13 H26 109.5 . . ? H25 C13 H26 109.5 . . ? H24 C13 H26 109.5 . . ? C10 C11 H27 109.5 . . ? C10 C11 H29 109.5 . . ? H27 C11 H29 109.5 . . ? C10 C11 H28 109.5 . . ? H27 C11 H28 109.5 . . ? H29 C11 H28 109.5 . . ? C21 C20 C25 112.37(14) . . ? C21 C20 B1 125.01(13) . . ? C25 C20 B1 122.62(13) . . ? F10 C25 C24 114.61(14) . . ? F10 C25 C20 120.25(14) . . ? C24 C25 C20 125.12(15) . . ? F9 C24 C23 119.68(15) . . ? F9 C24 C25 120.92(15) . . ? C23 C24 C25 119.39(15) . . ? F8 C23 C22 120.41(16) . . ? F8 C23 C24 120.78(16) . . ? C22 C23 C24 118.81(15) . . ? F7 C22 C23 120.06(15) . . ? F7 C22 C21 120.52(15) . . ? C23 C22 C21 119.42(15) . . ? F6 C21 C22 114.32(13) . . ? F6 C21 C20 120.78(13) . . ? C22 C21 C20 124.89(15) . . ? N1 B1 C1 103.88(12) . . ? N1 B1 C26 115.77(12) . . ? C1 B1 C26 105.78(12) . . ? N1 B1 C20 109.58(12) . . ? C1 B1 C20 114.42(12) . . ? C26 B1 C20 107.57(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 P1 N1 C14 -154.85(12) . . . . ? C10 P1 N1 C14 -41.05(14) . . . . ? C6 P1 N1 C14 87.67(13) . . . . ? C2 P1 N1 B1 14.18(11) . . . . ? C10 P1 N1 B1 127.98(10) . . . . ? C6 P1 N1 B1 -103.30(11) . . . . ? C16 C17 C18 C19 -0.5(3) . . . . ? C17 C18 C19 C14 1.5(3) . . . . ? C18 C19 C14 C15 -1.1(2) . . . . ? C18 C19 C14 N1 -178.88(14) . . . . ? B1 N1 C14 C19 113.37(16) . . . . ? P1 N1 C14 C19 -78.42(17) . . . . ? B1 N1 C14 C15 -64.37(19) . . . . ? P1 N1 C14 C15 103.84(15) . . . . ? N1 P1 C2 C1 -26.44(11) . . . . ? C10 P1 C2 C1 -143.39(10) . . . . ? C6 P1 C2 C1 93.67(11) . . . . ? N1 P1 C2 C3 -156.13(12) . . . . ? C10 P1 C2 C3 86.92(14) . . . . ? C6 P1 C2 C3 -36.02(15) . . . . ? C1 C2 C3 C4 53.68(19) . . . . ? P1 C2 C3 C4 178.00(12) . . . . ? C2 C3 C4 C5 63.22(19) . . . . ? C3 C2 C1 B1 163.29(13) . . . . ? P1 C2 C1 B1 30.85(14) . . . . ? C27 C26 C31 F1 -178.62(13) . . . . ? B1 C26 C31 F1 -3.6(2) . . . . ? C27 C26 C31 C30 1.8(2) . . . . ? B1 C26 C31 C30 176.83(15) . . . . ? F1 C31 C30 F5 -1.0(2) . . . . ? C26 C31 C30 F5 178.64(14) . . . . ? F1 C31 C30 C29 178.47(14) . . . . ? C26 C31 C30 C29 -1.9(3) . . . . ? F5 C30 C29 F2 0.4(2) . . . . ? C31 C30 C29 F2 -179.10(14) . . . . ? F5 C30 C29 C28 179.78(14) . . . . ? C31 C30 C29 C28 0.3(2) . . . . ? F2 C29 C28 F3 0.6(2) . . . . ? C30 C29 C28 F3 -178.82(14) . . . . ? F2 C29 C28 C27 -179.45(14) . . . . ? C30 C29 C28 C27 1.1(2) . . . . ? F3 C28 C27 F4 -0.5(2) . . . . ? C29 C28 C27 F4 179.52(14) . . . . ? F3 C28 C27 C26 178.72(14) . . . . ? C29 C28 C27 C26 -1.2(3) . . . . ? C31 C26 C27 F4 179.02(13) . . . . ? B1 C26 C27 F4 4.8(2) . . . . ? C31 C26 C27 C28 -0.2(2) . . . . ? B1 C26 C27 C28 -174.44(15) . . . . ? C18 C17 C16 C15 -0.8(3) . . . . ? C17 C16 C15 C14 1.2(3) . . . . ? C19 C14 C15 C16 -0.2(2) . . . . ? N1 C14 C15 C16 177.64(14) . . . . ? N1 P1 C6 C9 -53.63(14) . . . . ? C2 P1 C6 C9 -164.01(12) . . . . ? C10 P1 C6 C9 75.25(14) . . . . ? N1 P1 C6 C8 -175.92(11) . . . . ? C2 P1 C6 C8 73.70(13) . . . . ? C10 P1 C6 C8 -47.04(14) . . . . ? N1 P1 C6 C7 63.75(13) . . . . ? C2 P1 C6 C7 -46.63(13) . . . . ? C10 P1 C6 C7 -167.37(11) . . . . ? N1 P1 C10 C11 -41.30(13) . . . . ? C2 P1 C10 C11 66.57(13) . . . . ? C6 P1 C10 C11 -171.22(11) . . . . ? N1 P1 C10 C13 -158.07(11) . . . . ? C2 P1 C10 C13 -50.19(14) . . . . ? C6 P1 C10 C13 72.02(14) . . . . ? N1 P1 C10 C12 79.15(13) . . . . ? C2 P1 C10 C12 -172.97(12) . . . . ? C6 P1 C10 C12 -50.76(14) . . . . ? C21 C20 C25 F10 -178.37(13) . . . . ? B1 C20 C25 F10 1.1(2) . . . . ? C21 C20 C25 C24 -0.2(2) . . . . ? B1 C20 C25 C24 179.33(15) . . . . ? F10 C25 C24 F9 -1.3(2) . . . . ? C20 C25 C24 F9 -179.57(15) . . . . ? F10 C25 C24 C23 178.70(14) . . . . ? C20 C25 C24 C23 0.4(3) . . . . ? F9 C24 C23 F8 -0.4(2) . . . . ? C25 C24 C23 F8 179.56(15) . . . . ? F9 C24 C23 C22 179.90(15) . . . . ? C25 C24 C23 C22 -0.1(3) . . . . ? F8 C23 C22 F7 0.2(3) . . . . ? C24 C23 C22 F7 179.86(15) . . . . ? F8 C23 C22 C21 179.91(14) . . . . ? C24 C23 C22 C21 -0.4(3) . . . . ? F7 C22 C21 F6 1.6(2) . . . . ? C23 C22 C21 F6 -178.11(14) . . . . ? F7 C22 C21 C20 -179.59(14) . . . . ? C23 C22 C21 C20 0.7(3) . . . . ? C25 C20 C21 F6 178.37(13) . . . . ? B1 C20 C21 F6 -1.1(2) . . . . ? C25 C20 C21 C22 -0.4(2) . . . . ? B1 C20 C21 C22 -179.89(14) . . . . ? C14 N1 B1 C1 171.73(12) . . . . ? P1 N1 B1 C1 2.32(14) . . . . ? C14 N1 B1 C26 -72.78(17) . . . . ? P1 N1 B1 C26 117.81(12) . . . . ? C14 N1 B1 C20 49.05(17) . . . . ? P1 N1 B1 C20 -120.36(11) . . . . ? C2 C1 B1 N1 -22.32(16) . . . . ? C2 C1 B1 C26 -144.67(12) . . . . ? C2 C1 B1 C20 97.11(15) . . . . ? C27 C26 B1 N1 -9.4(2) . . . . ? C31 C26 B1 N1 176.53(13) . . . . ? C27 C26 B1 C1 104.96(18) . . . . ? C31 C26 B1 C1 -69.06(16) . . . . ? C27 C26 B1 C20 -132.35(16) . . . . ? C31 C26 B1 C20 53.63(17) . . . . ? C21 C20 B1 N1 90.41(17) . . . . ? C25 C20 B1 N1 -89.04(17) . . . . ? C21 C20 B1 C1 -25.8(2) . . . . ? C25 C20 B1 C1 154.78(14) . . . . ? C21 C20 B1 C26 -142.96(14) . . . . ? C25 C20 B1 C26 37.58(19) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.319 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.049 data_cj048_0m _database_code_depnum_ccdc_archive 'CCDC 910004' #TrackingRef 'CIFs-revised.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H39 B F10 N P' _chemical_formula_weight 825.55 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 19.5503(16) _cell_length_b 11.7262(8) _cell_length_c 33.928(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.717(3) _cell_angle_gamma 90.00 _cell_volume 7707.7(10) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5660 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 27.66 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3408 _exptl_absorpt_coefficient_mu 0.155 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9697 _exptl_absorpt_correction_T_max 0.9847 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26430 _diffrn_reflns_av_R_equivalents 0.0694 _diffrn_reflns_av_sigmaI/netI 0.1000 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 27.91 _reflns_number_total 9195 _reflns_number_gt 5336 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0582P)^2^+1.1084P] 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 9195 _refine_ls_number_parameters 531 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1132 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1345 _refine_ls_wR_factor_gt 0.1084 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.941 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.71803(11) 0.25425(18) 0.14096(7) 0.0136(5) Uani 1 1 d . . . C2 C 0.69398(12) 0.28783(18) 0.17573(8) 0.0190(6) Uani 1 1 d . . . H2 H 0.7194 0.2692 0.2007 0.023 Uiso 1 1 calc R . . C3 C 0.63254(13) 0.3489(2) 0.17410(9) 0.0265(6) Uani 1 1 d . . . H3 H 0.6159 0.3710 0.1980 0.032 Uiso 1 1 calc R . . C4 C 0.59580(13) 0.3775(2) 0.13784(10) 0.0294(7) Uani 1 1 d . . . H4 H 0.5540 0.4193 0.1367 0.035 Uiso 1 1 calc R . . C5 C 0.62025(13) 0.3448(2) 0.10336(9) 0.0269(6) Uani 1 1 d . . . H5 H 0.5950 0.3646 0.0784 0.032 Uiso 1 1 calc R . . C6 C 0.68113(13) 0.28365(19) 0.10456(8) 0.0208(6) Uani 1 1 d . . . H6 H 0.6976 0.2619 0.0805 0.025 Uiso 1 1 calc R . . C7 C 0.85982(12) 0.35557(18) 0.17612(8) 0.0142(5) Uani 1 1 d . . . C8 C 0.82337(12) 0.45585(19) 0.16552(8) 0.0176(5) Uani 1 1 d . . . C9 C 0.82195(13) 0.54974(19) 0.18971(9) 0.0223(6) Uani 1 1 d . . . C10 C 0.85949(13) 0.5492(2) 0.22687(8) 0.0241(6) Uani 1 1 d . . . C11 C 0.89672(13) 0.4532(2) 0.23927(8) 0.0228(6) Uani 1 1 d . . . C12 C 0.89588(12) 0.36025(19) 0.21425(8) 0.0183(5) Uani 1 1 d . . . C13 C 0.87402(12) 0.30055(18) 0.10107(7) 0.0144(5) Uani 1 1 d . . . C14 C 0.92533(12) 0.38286(19) 0.09975(8) 0.0184(5) Uani 1 1 d . . . C15 C 0.94470(13) 0.42738(19) 0.06549(8) 0.0218(6) Uani 1 1 d . . . C16 C 0.91378(13) 0.3888(2) 0.02912(8) 0.0228(6) Uani 1 1 d . . . C17 C 0.86413(13) 0.3056(2) 0.02829(8) 0.0216(6) Uani 1 1 d . . . C18 C 0.84607(12) 0.26442(19) 0.06347(8) 0.0169(5) Uani 1 1 d . . . C19 C 0.90916(12) 0.13634(18) 0.15589(8) 0.0134(5) Uani 1 1 d . . . C20 C 0.86894(12) 0.02885(18) 0.13874(8) 0.0143(5) Uani 1 1 d . . . C21 C 0.98063(12) 0.14372(18) 0.14336(8) 0.0153(5) Uani 1 1 d . . . C22 C 0.99207(13) 0.12798(19) 0.10417(8) 0.0197(6) Uani 1 1 d . . . H22 H 0.9545 0.1077 0.0847 0.024 Uiso 1 1 calc R . . C23 C 1.05739(13) 0.1413(2) 0.09281(9) 0.0251(6) Uani 1 1 d . . . H23 H 1.0637 0.1323 0.0657 0.030 Uiso 1 1 calc R . . C24 C 1.11324(14) 0.1677(2) 0.12101(10) 0.0299(7) Uani 1 1 d . . . H24 H 1.1581 0.1758 0.1135 0.036 Uiso 1 1 calc R . . C25 C 1.10297(13) 0.1819(2) 0.16002(9) 0.0274(7) Uani 1 1 d . . . H25 H 1.1410 0.1997 0.1795 0.033 Uiso 1 1 calc R . . C26 C 1.03747(12) 0.17054(19) 0.17119(8) 0.0216(6) Uani 1 1 d . . . H26 H 1.0313 0.1812 0.1983 0.026 Uiso 1 1 calc R . . C27 C 0.90018(12) -0.08799(18) 0.14903(8) 0.0175(5) Uani 1 1 d . . . C28 C 0.94122(13) -0.1116(2) 0.18483(9) 0.0255(6) Uani 1 1 d . . . H28 H 0.9499 -0.0535 0.2044 0.031 Uiso 1 1 calc R . . C29 C 0.96966(14) -0.2194(2) 0.19229(10) 0.0320(7) Uani 1 1 d . . . H29 H 0.9978 -0.2342 0.2168 0.038 Uiso 1 1 calc R . . C30 C 0.95735(15) -0.3050(2) 0.16426(10) 0.0353(8) Uani 1 1 d . . . H30 H 0.9766 -0.3788 0.1695 0.042 Uiso 1 1 calc R . . C31 C 0.91707(15) -0.2827(2) 0.12868(11) 0.0376(8) Uani 1 1 d . . . H31 H 0.9085 -0.3412 0.1093 0.045 Uiso 1 1 calc R . . C32 C 0.88889(13) -0.1753(2) 0.12105(9) 0.0263(6) Uani 1 1 d . . . H32 H 0.8614 -0.1609 0.0963 0.032 Uiso 1 1 calc R . . C33 C 0.71704(12) -0.03079(19) 0.12100(8) 0.0200(6) Uani 1 1 d . . . H33 H 0.7292 -0.1122 0.1273 0.024 Uiso 1 1 calc R . . C34 C 0.71634(14) -0.0180(2) 0.07606(8) 0.0286(7) Uani 1 1 d . . . H34A H 0.7631 -0.0292 0.0694 0.043 Uiso 1 1 calc R . . H34B H 0.7001 0.0586 0.0678 0.043 Uiso 1 1 calc R . . H34C H 0.6853 -0.0751 0.0622 0.043 Uiso 1 1 calc R . . C35 C 0.64342(13) -0.0135(2) 0.13199(9) 0.0280(7) Uani 1 1 d . . . H35A H 0.6444 -0.0218 0.1608 0.042 Uiso 1 1 calc R . . H35B H 0.6123 -0.0707 0.1183 0.042 Uiso 1 1 calc R . . H35C H 0.6269 0.0630 0.1239 0.042 Uiso 1 1 calc R . . C36 C 0.76879(13) 0.02075(19) 0.20223(8) 0.0183(6) Uani 1 1 d . . . H36 H 0.7216 0.0505 0.2048 0.022 Uiso 1 1 calc R . . C37 C 0.76554(14) -0.1079(2) 0.21142(9) 0.0278(7) Uani 1 1 d . . . H37A H 0.7345 -0.1457 0.1903 0.042 Uiso 1 1 calc R . . H37B H 0.7482 -0.1187 0.2370 0.042 Uiso 1 1 calc R . . H37C H 0.8118 -0.1409 0.2128 0.042 Uiso 1 1 calc R . . C38 C 0.81691(13) 0.0819(2) 0.23468(8) 0.0229(6) Uani 1 1 d . . . H38A H 0.8184 0.1634 0.2284 0.034 Uiso 1 1 calc R . . H38B H 0.8634 0.0496 0.2362 0.034 Uiso 1 1 calc R . . H38C H 0.7998 0.0721 0.2603 0.034 Uiso 1 1 calc R . . C39 C 0.77095(16) 0.9758(3) 0.97114(10) 0.0433(8) Uani 1 1 d . . . H39A H 0.7792 1.0574 0.9758 0.065 Uiso 1 1 calc R . . H39B H 0.7302 0.9524 0.9830 0.065 Uiso 1 1 calc R . . H39C H 0.7632 0.9610 0.9425 0.065 Uiso 1 1 calc R . . C40 C 0.83286(14) 0.9090(2) 0.98975(9) 0.0271(6) Uani 1 1 d . . . C41 C 0.89036(15) 0.9637(2) 1.00946(9) 0.0317(7) Uani 1 1 d . . . H41 H 0.8902 1.0445 1.0117 0.038 Uiso 1 1 calc R . . C42 C 0.94776(15) 0.9036(2) 1.02592(10) 0.0365(8) Uani 1 1 d . . . H42 H 0.9866 0.9432 1.0391 0.044 Uiso 1 1 calc R . . C43 C 0.94916(16) 0.7860(2) 1.02336(10) 0.0366(8) Uani 1 1 d . . . H43 H 0.9885 0.7441 1.0348 0.044 Uiso 1 1 calc R . . C44 C 0.89216(16) 0.7309(2) 1.00378(10) 0.0375(8) Uani 1 1 d . . . H44 H 0.8925 0.6501 1.0016 0.045 Uiso 1 1 calc R . . C45 C 0.83481(15) 0.7910(2) 0.98740(9) 0.0323(7) Uani 1 1 d . . . H45 H 0.7960 0.7510 0.9743 0.039 Uiso 1 1 calc R . . N1 N 0.78181(9) 0.19115(15) 0.14240(6) 0.0139(4) Uani 1 1 d . . . B1 B 0.85683(13) 0.2482(2) 0.14388(9) 0.0150(6) Uani 1 1 d . . . F1 F 0.78752(7) 0.46773(11) 0.12853(5) 0.0236(3) Uani 1 1 d . . . F2 F 0.78493(8) 0.64279(11) 0.17709(5) 0.0334(4) Uani 1 1 d . . . F3 F 0.86036(9) 0.64126(12) 0.25082(5) 0.0382(4) Uani 1 1 d . . . F4 F 0.93465(8) 0.45102(13) 0.27561(5) 0.0360(4) Uani 1 1 d . . . F5 F 0.93395(7) 0.27055(11) 0.22972(4) 0.0238(4) Uani 1 1 d . . . F6 F 0.79904(7) 0.17819(11) 0.05909(4) 0.0239(3) Uani 1 1 d . . . F7 F 0.83425(8) 0.26465(13) -0.00693(5) 0.0330(4) Uani 1 1 d . . . F8 F 0.93148(8) 0.43108(13) -0.00497(5) 0.0361(4) Uani 1 1 d . . . F9 F 0.99430(8) 0.50789(12) 0.06702(5) 0.0350(4) Uani 1 1 d . . . F10 F 0.96191(7) 0.42225(11) 0.13421(4) 0.0250(4) Uani 1 1 d . . . P1 P 0.78254(3) 0.05448(5) 0.15124(2) 0.01412(15) Uani 1 1 d . . . H19 H 0.8603(11) 0.0333(17) 0.1105(7) 0.008(6) Uiso 1 1 d . . . H20 H 0.9140(12) 0.1264(18) 0.1834(8) 0.011(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 C1 0.0116(11) 0.0126(10) 0.0167(14) -0.0010(10) 0.0018(10) -0.0002(9) C2 0.0172(13) 0.0161(11) 0.0240(16) 0.0006(11) 0.0041(11) 0.0017(10) C3 0.0256(15) 0.0254(13) 0.0305(18) -0.0005(12) 0.0112(13) 0.0053(11) C4 0.0179(14) 0.0247(13) 0.046(2) 0.0058(14) 0.0069(13) 0.0088(11) C5 0.0212(14) 0.0290(14) 0.0285(18) 0.0066(13) -0.0043(12) 0.0078(11) C6 0.0190(13) 0.0228(12) 0.0198(15) 0.0009(11) -0.0009(11) 0.0024(10) C7 0.0128(12) 0.0148(11) 0.0153(14) -0.0001(10) 0.0024(10) -0.0027(9) C8 0.0162(12) 0.0180(11) 0.0193(15) -0.0003(11) 0.0056(11) -0.0035(10) C9 0.0232(14) 0.0155(11) 0.0310(17) -0.0024(12) 0.0135(12) 0.0015(10) C10 0.0288(15) 0.0205(12) 0.0262(17) -0.0121(12) 0.0149(13) -0.0066(11) C11 0.0234(14) 0.0299(13) 0.0154(15) -0.0060(12) 0.0031(11) -0.0077(11) C12 0.0183(13) 0.0201(12) 0.0175(15) -0.0002(11) 0.0058(11) -0.0002(10) C13 0.0149(12) 0.0136(11) 0.0152(14) 0.0003(10) 0.0037(10) 0.0041(9) C14 0.0199(13) 0.0187(12) 0.0165(15) -0.0010(11) 0.0024(11) 0.0017(10) C15 0.0208(13) 0.0185(12) 0.0278(17) 0.0052(12) 0.0098(12) -0.0018(10) C16 0.0285(15) 0.0263(13) 0.0154(15) 0.0083(11) 0.0092(12) 0.0058(11) C17 0.0268(14) 0.0259(13) 0.0111(14) -0.0023(11) -0.0006(11) 0.0028(11) C18 0.0175(12) 0.0166(11) 0.0171(15) 0.0016(10) 0.0041(11) 0.0013(10) C19 0.0130(12) 0.0143(11) 0.0133(14) 0.0001(10) 0.0029(10) -0.0008(9) C20 0.0178(12) 0.0140(11) 0.0114(14) -0.0013(10) 0.0025(11) 0.0033(9) C21 0.0164(12) 0.0123(11) 0.0169(14) 0.0017(10) 0.0018(10) 0.0030(9) C22 0.0188(13) 0.0212(12) 0.0193(15) 0.0001(11) 0.0028(11) 0.0051(10) C23 0.0254(14) 0.0268(13) 0.0258(17) 0.0039(12) 0.0127(13) 0.0075(11) C24 0.0185(14) 0.0271(14) 0.047(2) 0.0020(14) 0.0135(14) -0.0008(11) C25 0.0185(14) 0.0271(14) 0.0359(19) -0.0018(13) 0.0005(13) -0.0034(11) C26 0.0191(13) 0.0212(12) 0.0240(16) -0.0019(11) 0.0007(12) -0.0005(10) C27 0.0168(12) 0.0134(11) 0.0236(15) 0.0023(10) 0.0078(11) 0.0007(9) C28 0.0240(14) 0.0277(13) 0.0259(17) 0.0019(12) 0.0068(12) 0.0067(11) C29 0.0277(15) 0.0332(15) 0.0359(19) 0.0178(14) 0.0080(14) 0.0114(13) C30 0.0318(16) 0.0183(13) 0.059(2) 0.0129(15) 0.0188(16) 0.0087(12) C31 0.0395(18) 0.0177(13) 0.056(2) -0.0041(14) 0.0073(17) 0.0054(12) C32 0.0264(15) 0.0203(13) 0.0319(18) -0.0063(12) 0.0036(13) 0.0011(11) C33 0.0201(13) 0.0150(11) 0.0242(16) -0.0032(11) 0.0003(11) -0.0033(10) C34 0.0301(16) 0.0306(14) 0.0231(17) -0.0052(12) -0.0034(13) -0.0066(12) C35 0.0194(14) 0.0293(14) 0.0342(19) -0.0014(13) -0.0006(13) -0.0051(11) C36 0.0197(13) 0.0169(11) 0.0194(15) 0.0028(11) 0.0070(11) 0.0017(10) C37 0.0349(16) 0.0206(13) 0.0288(18) 0.0061(12) 0.0078(13) -0.0010(12) C38 0.0273(14) 0.0296(13) 0.0123(14) 0.0041(11) 0.0049(11) 0.0008(11) C39 0.0396(18) 0.0503(19) 0.039(2) 0.0069(16) -0.0001(16) 0.0077(15) C40 0.0280(15) 0.0328(14) 0.0219(16) -0.0004(13) 0.0085(12) 0.0025(12) C41 0.0368(17) 0.0239(13) 0.0357(19) -0.0038(13) 0.0091(14) 0.0030(12) C42 0.0324(17) 0.0356(16) 0.039(2) -0.0062(15) -0.0031(15) 0.0005(13) C43 0.0366(17) 0.0384(16) 0.034(2) 0.0025(14) 0.0035(15) 0.0110(14) C44 0.0451(19) 0.0215(13) 0.046(2) -0.0017(14) 0.0078(16) 0.0015(13) C45 0.0291(16) 0.0322(15) 0.036(2) -0.0035(14) 0.0068(14) -0.0067(13) N1 0.0136(10) 0.0131(9) 0.0148(12) 0.0013(8) 0.0015(9) 0.0028(8) B1 0.0127(13) 0.0171(13) 0.0143(16) -0.0017(11) -0.0009(11) 0.0007(11) F1 0.0238(8) 0.0222(7) 0.0237(9) 0.0012(6) -0.0009(7) 0.0039(6) F2 0.0364(9) 0.0167(7) 0.0488(12) -0.0036(7) 0.0119(8) 0.0080(6) F3 0.0525(11) 0.0269(8) 0.0389(11) -0.0207(8) 0.0194(9) -0.0073(7) F4 0.0444(10) 0.0428(9) 0.0191(9) -0.0121(8) -0.0013(8) -0.0059(8) F5 0.0259(8) 0.0262(7) 0.0170(9) -0.0025(6) -0.0058(7) 0.0037(6) F6 0.0266(8) 0.0277(7) 0.0171(9) -0.0044(6) 0.0020(7) -0.0075(6) F7 0.0425(10) 0.0426(9) 0.0127(9) -0.0006(7) 0.0002(7) -0.0008(8) F8 0.0472(10) 0.0430(9) 0.0211(10) 0.0116(8) 0.0152(8) -0.0002(8) F9 0.0355(9) 0.0332(8) 0.0386(11) 0.0041(8) 0.0137(8) -0.0146(7) F10 0.0276(8) 0.0265(8) 0.0211(9) -0.0039(7) 0.0036(7) -0.0092(6) P1 0.0138(3) 0.0128(3) 0.0156(4) -0.0003(3) 0.0014(3) 0.0008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.384(3) . ? C1 C6 1.387(3) . ? C1 N1 1.445(3) . ? C2 C3 1.393(3) . ? C2 H2 0.9500 . ? C3 C4 1.380(4) . ? C3 H3 0.9500 . ? C4 C5 1.376(4) . ? C4 H4 0.9500 . ? C5 C6 1.386(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C12 1.389(3) . ? C7 C8 1.397(3) . ? C7 B1 1.664(3) . ? C8 F1 1.360(3) . ? C8 C9 1.376(3) . ? C9 F2 1.347(3) . ? C9 C10 1.371(4) . ? C10 F3 1.350(3) . ? C10 C11 1.375(4) . ? C11 F4 1.351(3) . ? C11 C12 1.381(3) . ? C12 F5 1.353(3) . ? C13 C18 1.385(3) . ? C13 C14 1.397(3) . ? C13 B1 1.653(4) . ? C14 F10 1.366(3) . ? C14 C15 1.373(4) . ? C15 F9 1.349(3) . ? C15 C16 1.376(4) . ? C16 F8 1.346(3) . ? C16 C17 1.374(4) . ? C17 F7 1.346(3) . ? C17 C18 1.377(4) . ? C18 F6 1.361(3) . ? C19 C21 1.517(3) . ? C19 C20 1.556(3) . ? C19 B1 1.680(3) . ? C19 H20 0.93(2) . ? C20 C27 1.521(3) . ? C20 P1 1.821(2) . ? C20 H19 0.95(2) . ? C21 C22 1.390(4) . ? C21 C26 1.394(3) . ? C22 C23 1.391(3) . ? C22 H22 0.9500 . ? C23 C24 1.387(4) . ? C23 H23 0.9500 . ? C24 C25 1.375(4) . ? C24 H24 0.9500 . ? C25 C26 1.390(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C28 1.391(4) . ? C27 C32 1.393(3) . ? C28 C29 1.390(3) . ? C28 H28 0.9500 . ? C29 C30 1.382(4) . ? C29 H29 0.9500 . ? C30 C31 1.375(4) . ? C30 H30 0.9500 . ? C31 C32 1.386(3) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 C34 1.530(4) . ? C33 C35 1.548(4) . ? C33 P1 1.827(2) . ? C33 H33 1.0000 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 C38 1.528(3) . ? C36 C37 1.543(3) . ? C36 P1 1.829(3) . ? C36 H36 1.0000 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 C40 1.507(4) . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 C41 1.386(4) . ? C40 C45 1.388(4) . ? C41 C42 1.379(4) . ? C41 H41 0.9500 . ? C42 C43 1.382(4) . ? C42 H42 0.9500 . ? C43 C44 1.379(4) . ? C43 H43 0.9500 . ? C44 C45 1.377(4) . ? C44 H44 0.9500 . ? C45 H45 0.9500 . ? N1 B1 1.607(3) . ? N1 P1 1.6301(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 C2 C1 C6 119.5(2) . . ? C2 C1 N1 120.5(2) . . ? C6 C1 N1 120.0(2) . . ? C1 C2 C3 120.1(2) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 120.2(3) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 119.5(2) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 120.9(3) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C1 119.8(3) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? C12 C7 C8 112.6(2) . . ? C12 C7 B1 127.7(2) . . ? C8 C7 B1 119.7(2) . . ? F1 C8 C9 114.8(2) . . ? F1 C8 C7 120.4(2) . . ? C9 C8 C7 124.8(2) . . ? F2 C9 C10 119.6(2) . . ? F2 C9 C8 120.8(2) . . ? C10 C9 C8 119.6(2) . . ? F3 C10 C9 120.8(2) . . ? F3 C10 C11 120.4(3) . . ? C9 C10 C11 118.8(2) . . ? F4 C11 C10 119.9(2) . . ? F4 C11 C12 120.4(2) . . ? C10 C11 C12 119.7(2) . . ? F5 C12 C11 114.5(2) . . ? F5 C12 C7 121.0(2) . . ? C11 C12 C7 124.5(2) . . ? C18 C13 C14 112.2(2) . . ? C18 C13 B1 126.5(2) . . ? C14 C13 B1 121.1(2) . . ? F10 C14 C15 115.1(2) . . ? F10 C14 C13 120.1(2) . . ? C15 C14 C13 124.8(2) . . ? F9 C15 C14 120.8(2) . . ? F9 C15 C16 119.4(2) . . ? C14 C15 C16 119.8(2) . . ? F8 C16 C17 120.4(2) . . ? F8 C16 C15 121.2(2) . . ? C17 C16 C15 118.4(2) . . ? F7 C17 C16 119.5(2) . . ? F7 C17 C18 120.9(2) . . ? C16 C17 C18 119.6(2) . . ? F6 C18 C17 114.5(2) . . ? F6 C18 C13 120.3(2) . . ? C17 C18 C13 125.1(2) . . ? C21 C19 C20 112.31(19) . . ? C21 C19 B1 116.21(19) . . ? C20 C19 B1 106.32(18) . . ? C21 C19 H20 108.3(14) . . ? C20 C19 H20 104.6(14) . . ? B1 C19 H20 108.5(14) . . ? C27 C20 C19 118.5(2) . . ? C27 C20 P1 116.84(17) . . ? C19 C20 P1 102.54(15) . . ? C27 C20 H19 107.0(13) . . ? C19 C20 H19 110.1(13) . . ? P1 C20 H19 100.4(14) . . ? C22 C21 C26 117.5(2) . . ? C22 C21 C19 122.2(2) . . ? C26 C21 C19 120.2(2) . . ? C21 C22 C23 121.4(2) . . ? C21 C22 H22 119.3 . . ? C23 C22 H22 119.3 . . ? C24 C23 C22 120.1(3) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C25 C24 C23 119.2(3) . . ? C25 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? C24 C25 C26 120.7(3) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C25 C26 C21 121.1(3) . . ? C25 C26 H26 119.4 . . ? C21 C26 H26 119.4 . . ? C28 C27 C32 118.0(2) . . ? C28 C27 C20 123.1(2) . . ? C32 C27 C20 118.9(2) . . ? C27 C28 C29 120.6(3) . . ? C27 C28 H28 119.7 . . ? C29 C28 H28 119.7 . . ? C30 C29 C28 120.5(3) . . ? C30 C29 H29 119.8 . . ? C28 C29 H29 119.8 . . ? C31 C30 C29 119.5(2) . . ? C31 C30 H30 120.3 . . ? C29 C30 H30 120.3 . . ? C30 C31 C32 120.2(3) . . ? C30 C31 H31 119.9 . . ? C32 C31 H31 119.9 . . ? C31 C32 C27 121.2(3) . . ? C31 C32 H32 119.4 . . ? C27 C32 H32 119.4 . . ? C34 C33 C35 110.1(2) . . ? C34 C33 P1 114.69(17) . . ? C35 C33 P1 113.39(18) . . ? C34 C33 H33 106.0 . . ? C35 C33 H33 106.0 . . ? P1 C33 H33 106.0 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C38 C36 C37 110.6(2) . . ? C38 C36 P1 115.18(17) . . ? C37 C36 P1 114.69(18) . . ? C38 C36 H36 105.1 . . ? C37 C36 H36 105.1 . . ? P1 C36 H36 105.1 . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C36 C38 H38A 109.5 . . ? C36 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C36 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C40 C39 H39A 109.5 . . ? C40 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C40 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C41 C40 C45 117.6(3) . . ? C41 C40 C39 121.0(3) . . ? C45 C40 C39 121.4(3) . . ? C42 C41 C40 121.5(3) . . ? C42 C41 H41 119.3 . . ? C40 C41 H41 119.3 . . ? C43 C42 C41 120.5(3) . . ? C43 C42 H42 119.8 . . ? C41 C42 H42 119.8 . . ? C44 C43 C42 118.4(3) . . ? C44 C43 H43 120.8 . . ? C42 C43 H43 120.8 . . ? C45 C44 C43 121.1(3) . . ? C45 C44 H44 119.4 . . ? C43 C44 H44 119.4 . . ? C44 C45 C40 121.0(3) . . ? C44 C45 H45 119.5 . . ? C40 C45 H45 119.5 . . ? C1 N1 B1 124.59(17) . . ? C1 N1 P1 119.72(15) . . ? B1 N1 P1 114.73(14) . . ? N1 B1 C13 114.82(19) . . ? N1 B1 C7 106.67(19) . . ? C13 B1 C7 107.67(18) . . ? N1 B1 C19 101.90(17) . . ? C13 B1 C19 108.31(19) . . ? C7 B1 C19 117.7(2) . . ? N1 P1 C33 116.52(11) . . ? N1 P1 C20 96.01(10) . . ? C33 P1 C20 112.39(11) . . ? N1 P1 C36 112.82(10) . . ? C33 P1 C36 103.40(12) . . ? C20 P1 C36 116.31(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.1(3) . . . . ? N1 C1 C2 C3 179.8(2) . . . . ? C1 C2 C3 C4 -0.8(4) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? C3 C4 C5 C6 0.1(4) . . . . ? C4 C5 C6 C1 0.2(4) . . . . ? C2 C1 C6 C5 -0.9(3) . . . . ? N1 C1 C6 C5 -179.6(2) . . . . ? C12 C7 C8 F1 177.2(2) . . . . ? B1 C7 C8 F1 -2.4(3) . . . . ? C12 C7 C8 C9 -0.6(4) . . . . ? B1 C7 C8 C9 179.9(2) . . . . ? F1 C8 C9 F2 2.5(3) . . . . ? C7 C8 C9 F2 -179.6(2) . . . . ? F1 C8 C9 C10 -176.5(2) . . . . ? C7 C8 C9 C10 1.4(4) . . . . ? F2 C9 C10 F3 -0.7(4) . . . . ? C8 C9 C10 F3 178.3(2) . . . . ? F2 C9 C10 C11 179.8(2) . . . . ? C8 C9 C10 C11 -1.2(4) . . . . ? F3 C10 C11 F4 -0.2(4) . . . . ? C9 C10 C11 F4 179.4(2) . . . . ? F3 C10 C11 C12 -179.3(2) . . . . ? C9 C10 C11 C12 0.3(4) . . . . ? F4 C11 C12 F5 1.4(3) . . . . ? C10 C11 C12 F5 -179.5(2) . . . . ? F4 C11 C12 C7 -178.5(2) . . . . ? C10 C11 C12 C7 0.6(4) . . . . ? C8 C7 C12 F5 179.7(2) . . . . ? B1 C7 C12 F5 -0.8(4) . . . . ? C8 C7 C12 C11 -0.5(4) . . . . ? B1 C7 C12 C11 179.1(2) . . . . ? C18 C13 C14 F10 -175.4(2) . . . . ? B1 C13 C14 F10 -0.6(3) . . . . ? C18 C13 C14 C15 2.5(3) . . . . ? B1 C13 C14 C15 177.3(2) . . . . ? F10 C14 C15 F9 -2.9(3) . . . . ? C13 C14 C15 F9 179.1(2) . . . . ? F10 C14 C15 C16 176.4(2) . . . . ? C13 C14 C15 C16 -1.5(4) . . . . ? F9 C15 C16 F8 -0.9(4) . . . . ? C14 C15 C16 F8 179.8(2) . . . . ? F9 C15 C16 C17 179.1(2) . . . . ? C14 C15 C16 C17 -0.3(4) . . . . ? F8 C16 C17 F7 1.5(4) . . . . ? C15 C16 C17 F7 -178.5(2) . . . . ? F8 C16 C17 C18 -179.2(2) . . . . ? C15 C16 C17 C18 0.9(4) . . . . ? F7 C17 C18 F6 2.6(3) . . . . ? C16 C17 C18 F6 -176.7(2) . . . . ? F7 C17 C18 C13 179.6(2) . . . . ? C16 C17 C18 C13 0.3(4) . . . . ? C14 C13 C18 F6 175.02(19) . . . . ? B1 C13 C18 F6 0.6(4) . . . . ? C14 C13 C18 C17 -1.9(3) . . . . ? B1 C13 C18 C17 -176.3(2) . . . . ? C21 C19 C20 C27 58.8(3) . . . . ? B1 C19 C20 C27 -173.1(2) . . . . ? C21 C19 C20 P1 -170.94(17) . . . . ? B1 C19 C20 P1 -42.8(2) . . . . ? C20 C19 C21 C22 47.4(3) . . . . ? B1 C19 C21 C22 -75.3(3) . . . . ? C20 C19 C21 C26 -134.6(2) . . . . ? B1 C19 C21 C26 102.7(3) . . . . ? C26 C21 C22 C23 -1.6(3) . . . . ? C19 C21 C22 C23 176.4(2) . . . . ? C21 C22 C23 C24 1.9(4) . . . . ? C22 C23 C24 C25 -0.9(4) . . . . ? C23 C24 C25 C26 -0.2(4) . . . . ? C24 C25 C26 C21 0.4(4) . . . . ? C22 C21 C26 C25 0.5(3) . . . . ? C19 C21 C26 C25 -177.6(2) . . . . ? C19 C20 C27 C28 31.4(3) . . . . ? P1 C20 C27 C28 -92.1(3) . . . . ? C19 C20 C27 C32 -147.0(2) . . . . ? P1 C20 C27 C32 89.6(3) . . . . ? C32 C27 C28 C29 -0.3(4) . . . . ? C20 C27 C28 C29 -178.6(2) . . . . ? C27 C28 C29 C30 -0.3(4) . . . . ? C28 C29 C30 C31 0.5(4) . . . . ? C29 C30 C31 C32 -0.2(5) . . . . ? C30 C31 C32 C27 -0.3(4) . . . . ? C28 C27 C32 C31 0.6(4) . . . . ? C20 C27 C32 C31 179.0(2) . . . . ? C45 C40 C41 C42 0.5(4) . . . . ? C39 C40 C41 C42 -178.7(3) . . . . ? C40 C41 C42 C43 -0.4(5) . . . . ? C41 C42 C43 C44 0.5(5) . . . . ? C42 C43 C44 C45 -0.6(5) . . . . ? C43 C44 C45 C40 0.6(5) . . . . ? C41 C40 C45 C44 -0.6(4) . . . . ? C39 C40 C45 C44 178.6(3) . . . . ? C2 C1 N1 B1 -88.4(3) . . . . ? C6 C1 N1 B1 90.3(3) . . . . ? C2 C1 N1 P1 79.8(2) . . . . ? C6 C1 N1 P1 -101.6(2) . . . . ? C1 N1 B1 C13 -75.9(3) . . . . ? P1 N1 B1 C13 115.40(18) . . . . ? C1 N1 B1 C7 43.3(3) . . . . ? P1 N1 B1 C7 -125.41(17) . . . . ? C1 N1 B1 C19 167.3(2) . . . . ? P1 N1 B1 C19 -1.4(2) . . . . ? C18 C13 B1 N1 -26.8(3) . . . . ? C14 C13 B1 N1 159.1(2) . . . . ? C18 C13 B1 C7 -145.5(2) . . . . ? C14 C13 B1 C7 40.5(3) . . . . ? C18 C13 B1 C19 86.2(3) . . . . ? C14 C13 B1 C19 -87.8(2) . . . . ? C12 C7 B1 N1 106.7(3) . . . . ? C8 C7 B1 N1 -73.8(3) . . . . ? C12 C7 B1 C13 -129.6(3) . . . . ? C8 C7 B1 C13 49.9(3) . . . . ? C12 C7 B1 C19 -6.9(4) . . . . ? C8 C7 B1 C19 172.6(2) . . . . ? C21 C19 B1 N1 155.0(2) . . . . ? C20 C19 B1 N1 29.2(2) . . . . ? C21 C19 B1 C13 33.5(3) . . . . ? C20 C19 B1 C13 -92.3(2) . . . . ? C21 C19 B1 C7 -88.8(3) . . . . ? C20 C19 B1 C7 145.4(2) . . . . ? C1 N1 P1 C33 50.3(2) . . . . ? B1 N1 P1 C33 -140.43(17) . . . . ? C1 N1 P1 C20 169.02(19) . . . . ? B1 N1 P1 C20 -21.70(19) . . . . ? C1 N1 P1 C36 -69.1(2) . . . . ? B1 N1 P1 C36 100.16(18) . . . . ? C34 C33 P1 N1 55.1(2) . . . . ? C35 C33 P1 N1 -72.5(2) . . . . ? C34 C33 P1 C20 -54.3(2) . . . . ? C35 C33 P1 C20 178.10(18) . . . . ? C34 C33 P1 C36 179.48(18) . . . . ? C35 C33 P1 C36 51.9(2) . . . . ? C27 C20 P1 N1 169.88(19) . . . . ? C19 C20 P1 N1 38.60(17) . . . . ? C27 C20 P1 C33 -68.2(2) . . . . ? C19 C20 P1 C33 160.54(15) . . . . ? C27 C20 P1 C36 50.7(2) . . . . ? C19 C20 P1 C36 -80.56(17) . . . . ? C38 C36 P1 N1 -52.8(2) . . . . ? C37 C36 P1 N1 177.19(17) . . . . ? C38 C36 P1 C33 -179.50(17) . . . . ? C37 C36 P1 C33 50.4(2) . . . . ? C38 C36 P1 C20 56.8(2) . . . . ? C37 C36 P1 C20 -73.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.91 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.344 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.067 #===end