# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_cj017_0m _database_code_depnum_ccdc_archive 'CCDC 892970' #TrackingRef 'All-cifs.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H14 B F15 O5' _chemical_formula_weight 714.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' O O 0.0106 0.0060 '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' _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 9.6725(5) _cell_length_b 10.5484(5) _cell_length_c 14.8047(7) _cell_angle_alpha 82.430(2) _cell_angle_beta 76.525(3) _cell_angle_gamma 77.604(2) _cell_volume 1429.37(12) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.659 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.176 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9490 _exptl_absorpt_correction_T_max 0.9740 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 35526 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 32.06 _reflns_number_total 9865 _reflns_number_gt 7130 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0596P)^2^+0.3066P] 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 9865 _refine_ls_number_parameters 433 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0636 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1243 _refine_ls_wR_factor_gt 0.1125 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 1.02581(14) 0.63433(12) 0.15229(9) 0.0214(2) Uani 1 1 d . . . O1 O 0.99690(9) 0.66435(9) 0.24180(6) 0.02618(18) Uani 1 1 d . . . O2 O 1.21754(9) 0.70380(9) 0.25564(6) 0.02854(19) Uani 1 1 d . . . O3 O 0.93647(9) 0.56591(8) 0.12864(6) 0.02321(16) Uani 1 1 d . . . O4 O 0.69092(10) 0.61564(10) 0.18832(8) 0.0382(2) Uani 1 1 d . . . F1 F 1.05559(12) 0.89744(9) 0.08985(7) 0.0513(2) Uani 1 1 d . . . F2 F 1.25556(17) 0.97037(12) -0.05778(8) 0.0753(4) Uani 1 1 d . . . F3 F 1.46019(15) 0.78527(15) -0.15046(8) 0.0799(4) Uani 1 1 d . . . F4 F 1.46258(11) 0.52909(13) -0.09720(8) 0.0627(3) Uani 1 1 d . . . F5 F 1.25658(10) 0.45648(9) 0.04561(7) 0.0421(2) Uani 1 1 d . . . F6 F 0.82669(10) 1.06549(8) 0.31226(7) 0.0435(2) Uani 1 1 d . . . F7 F 0.53624(10) 1.11720(8) 0.36064(7) 0.0455(2) Uani 1 1 d . . . F8 F 0.38910(8) 0.92027(9) 0.43377(6) 0.0400(2) Uani 1 1 d . . . F9 F 0.53703(9) 0.67476(8) 0.46221(6) 0.0398(2) Uani 1 1 d . . . F10 F 0.82801(8) 0.62390(7) 0.42163(6) 0.03237(17) Uani 1 1 d . . . F11 F 0.99457(10) 0.29676(9) 0.09241(6) 0.0406(2) Uani 1 1 d . . . F12 F 1.24242(11) 0.12537(10) 0.09468(6) 0.0470(2) Uani 1 1 d . . . F13 F 1.34499(9) 0.06282(8) 0.25355(6) 0.03664(19) Uani 1 1 d . . . F14 F 1.20109(10) 0.18334(9) 0.41014(6) 0.0405(2) Uani 1 1 d . . . F15 F 0.95567(9) 0.35800(8) 0.40876(5) 0.0382(2) Uani 1 1 d . . . C1 C 1.14985(13) 0.67505(12) 0.07161(8) 0.0240(2) Uani 1 1 d . . . C2 C 1.15488(16) 0.80492(14) 0.04379(9) 0.0337(3) Uani 1 1 d . . . C3 C 1.2564(2) 0.84345(17) -0.03106(11) 0.0464(4) Uani 1 1 d . . . C4 C 1.35911(19) 0.75001(19) -0.07844(10) 0.0484(4) Uani 1 1 d . . . C5 C 1.35975(16) 0.61989(18) -0.05223(10) 0.0406(3) Uani 1 1 d . . . C6 C 1.25428(14) 0.58439(14) 0.02139(9) 0.0299(3) Uani 1 1 d . . . C7 C 1.07143(12) 0.73066(12) 0.28254(8) 0.0241(2) Uani 1 1 d . . . C8 C 0.99941(12) 0.81575(12) 0.34385(8) 0.0244(2) Uani 1 1 d . . . C9 C 1.07470(15) 0.88465(14) 0.39506(10) 0.0334(3) Uani 1 1 d . . . H9A H 1.1798 0.8579 0.3747 0.050 Uiso 1 1 calc R . . H9B H 1.0463 0.8620 0.4622 0.050 Uiso 1 1 calc R . . H9C H 1.0471 0.9790 0.3816 0.050 Uiso 1 1 calc R . . C10 C 1.28660(15) 0.56921(15) 0.27507(10) 0.0344(3) Uani 1 1 d . . . H10A H 1.3921 0.5595 0.2498 0.041 Uiso 1 1 calc R . . H10B H 1.2491 0.5119 0.2426 0.041 Uiso 1 1 calc R . . C11 C 1.26097(19) 0.5258(2) 0.37735(11) 0.0504(4) Uani 1 1 d . . . H11A H 1.3096 0.4349 0.3865 0.076 Uiso 1 1 calc R . . H11B H 1.1567 0.5333 0.4026 0.076 Uiso 1 1 calc R . . H11C H 1.2998 0.5809 0.4097 0.076 Uiso 1 1 calc R . . C12 C 0.83840(13) 0.84227(11) 0.36420(8) 0.0233(2) Uani 1 1 d . . . C13 C 0.75828(14) 0.96662(12) 0.34990(9) 0.0288(2) Uani 1 1 d . . . C14 C 0.60829(14) 0.99467(13) 0.37257(10) 0.0309(3) Uani 1 1 d . . . C15 C 0.53418(13) 0.89557(13) 0.40988(9) 0.0290(2) Uani 1 1 d . . . C16 C 0.60950(13) 0.77064(13) 0.42445(9) 0.0272(2) Uani 1 1 d . . . C17 C 0.75932(13) 0.74510(11) 0.40272(8) 0.0236(2) Uani 1 1 d . . . C18 C 0.81767(12) 0.53414(11) 0.19281(8) 0.0235(2) Uani 1 1 d . . . C19 C 0.82436(13) 0.42707(12) 0.25184(9) 0.0249(2) Uani 1 1 d . . . C20 C 0.69104(14) 0.39650(14) 0.32050(11) 0.0359(3) Uani 1 1 d . . . H20A H 0.6076 0.4656 0.3132 0.054 Uiso 1 1 calc R . . H20B H 0.7065 0.3911 0.3841 0.054 Uiso 1 1 calc R . . H20C H 0.6725 0.3131 0.3087 0.054 Uiso 1 1 calc R . . C21 C 0.68910(15) 0.74330(13) 0.14121(11) 0.0334(3) Uani 1 1 d . . . H21A H 0.7479 0.7378 0.0769 0.040 Uiso 1 1 calc R . . H21B H 0.7303 0.7966 0.1746 0.040 Uiso 1 1 calc R . . C22 C 0.53536(17) 0.80398(16) 0.13895(15) 0.0496(4) Uani 1 1 d . . . H22A H 0.5312 0.8917 0.1068 0.074 Uiso 1 1 calc R . . H22B H 0.4783 0.8095 0.2028 0.074 Uiso 1 1 calc R . . H22C H 0.4957 0.7506 0.1057 0.074 Uiso 1 1 calc R . . C23 C 0.96451(12) 0.33559(11) 0.25021(8) 0.0229(2) Uani 1 1 d . . . C24 C 1.04329(14) 0.27284(12) 0.17193(8) 0.0268(2) Uani 1 1 d . . . C25 C 1.17063(14) 0.18382(13) 0.17183(9) 0.0294(2) Uani 1 1 d . . . C26 C 1.22439(13) 0.15214(12) 0.25222(9) 0.0264(2) Uani 1 1 d . . . C27 C 1.15023(14) 0.21289(12) 0.33153(8) 0.0270(2) Uani 1 1 d . . . C28 C 1.02336(13) 0.30201(12) 0.32975(8) 0.0252(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0197(5) 0.0220(6) 0.0221(6) 0.0007(4) -0.0038(4) -0.0053(4) O1 0.0225(4) 0.0361(5) 0.0222(4) -0.0071(3) 0.0004(3) -0.0133(4) O2 0.0193(4) 0.0383(5) 0.0275(4) -0.0029(3) 0.0004(3) -0.0101(4) O3 0.0231(4) 0.0260(4) 0.0219(4) 0.0002(3) -0.0045(3) -0.0093(3) O4 0.0224(4) 0.0291(5) 0.0567(6) 0.0158(4) -0.0064(4) -0.0052(4) F1 0.0651(6) 0.0286(4) 0.0524(6) 0.0009(4) 0.0000(5) -0.0083(4) F2 0.1141(11) 0.0568(7) 0.0583(7) 0.0190(5) -0.0030(7) -0.0545(7) F3 0.0829(8) 0.1258(11) 0.0383(6) -0.0053(6) 0.0212(5) -0.0739(9) F4 0.0402(5) 0.0967(9) 0.0499(6) -0.0386(6) 0.0179(4) -0.0201(6) F5 0.0392(5) 0.0352(4) 0.0476(5) -0.0119(4) 0.0031(4) -0.0060(4) F6 0.0378(4) 0.0255(4) 0.0660(6) 0.0051(4) -0.0066(4) -0.0135(3) F7 0.0364(5) 0.0291(4) 0.0685(6) 0.0014(4) -0.0152(4) 0.0002(4) F8 0.0210(3) 0.0481(5) 0.0503(5) -0.0026(4) -0.0082(3) -0.0054(3) F9 0.0301(4) 0.0387(5) 0.0487(5) 0.0065(4) -0.0001(4) -0.0176(4) F10 0.0303(4) 0.0253(4) 0.0359(4) 0.0051(3) -0.0003(3) -0.0050(3) F11 0.0500(5) 0.0455(5) 0.0293(4) -0.0083(3) -0.0209(4) 0.0011(4) F12 0.0532(5) 0.0497(5) 0.0297(4) -0.0150(4) -0.0035(4) 0.0095(4) F13 0.0284(4) 0.0349(4) 0.0391(4) 0.0000(3) -0.0043(3) 0.0051(3) F14 0.0441(5) 0.0470(5) 0.0273(4) -0.0012(3) -0.0164(3) 0.0069(4) F15 0.0449(5) 0.0385(4) 0.0229(4) -0.0057(3) -0.0039(3) 0.0082(4) C1 0.0235(5) 0.0315(6) 0.0188(5) 0.0001(4) -0.0038(4) -0.0112(5) C2 0.0416(7) 0.0348(7) 0.0265(6) 0.0034(5) -0.0052(5) -0.0170(6) C3 0.0623(10) 0.0516(9) 0.0323(7) 0.0091(6) -0.0059(7) -0.0379(8) C4 0.0508(9) 0.0795(12) 0.0229(6) -0.0025(7) 0.0049(6) -0.0444(9) C5 0.0318(7) 0.0673(10) 0.0261(6) -0.0170(6) 0.0052(5) -0.0213(7) C6 0.0263(6) 0.0399(7) 0.0258(6) -0.0071(5) -0.0015(5) -0.0132(5) C7 0.0204(5) 0.0315(6) 0.0222(5) -0.0014(4) -0.0030(4) -0.0113(4) C8 0.0220(5) 0.0284(6) 0.0244(5) -0.0018(4) -0.0030(4) -0.0103(4) C9 0.0318(6) 0.0387(7) 0.0352(7) -0.0096(5) -0.0063(5) -0.0155(6) C10 0.0252(6) 0.0431(8) 0.0317(7) -0.0022(5) -0.0028(5) -0.0036(6) C11 0.0417(8) 0.0677(11) 0.0350(8) 0.0089(7) -0.0072(6) -0.0044(8) C12 0.0232(5) 0.0262(6) 0.0217(5) -0.0029(4) -0.0029(4) -0.0085(4) C13 0.0286(6) 0.0247(6) 0.0343(6) -0.0004(5) -0.0061(5) -0.0101(5) C14 0.0287(6) 0.0263(6) 0.0378(7) -0.0017(5) -0.0102(5) -0.0025(5) C15 0.0217(5) 0.0355(7) 0.0309(6) -0.0041(5) -0.0063(5) -0.0067(5) C16 0.0251(5) 0.0319(6) 0.0258(6) -0.0001(4) -0.0027(4) -0.0123(5) C17 0.0243(5) 0.0239(5) 0.0216(5) -0.0009(4) -0.0023(4) -0.0056(4) C18 0.0196(5) 0.0236(5) 0.0282(6) 0.0000(4) -0.0050(4) -0.0073(4) C19 0.0217(5) 0.0237(5) 0.0290(6) 0.0012(4) -0.0050(4) -0.0067(4) C20 0.0249(6) 0.0299(7) 0.0470(8) 0.0077(5) 0.0006(5) -0.0080(5) C21 0.0299(6) 0.0236(6) 0.0441(7) 0.0082(5) -0.0086(5) -0.0058(5) C22 0.0313(7) 0.0309(7) 0.0797(12) 0.0127(7) -0.0121(8) -0.0014(6) C23 0.0230(5) 0.0219(5) 0.0241(5) 0.0017(4) -0.0050(4) -0.0072(4) C24 0.0307(6) 0.0289(6) 0.0229(5) -0.0016(4) -0.0098(4) -0.0060(5) C25 0.0322(6) 0.0302(6) 0.0235(6) -0.0056(4) -0.0019(5) -0.0032(5) C26 0.0233(5) 0.0243(5) 0.0285(6) 0.0002(4) -0.0033(4) -0.0015(4) C27 0.0304(6) 0.0274(6) 0.0226(5) 0.0016(4) -0.0081(4) -0.0037(5) C28 0.0286(6) 0.0247(5) 0.0200(5) -0.0007(4) -0.0024(4) -0.0038(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 O1 1.3544(15) . ? B1 O3 1.3659(15) . ? B1 C1 1.5713(17) . ? O1 C7 1.3796(14) . ? O2 C7 1.3534(14) . ? O2 C10 1.4558(17) . ? O3 C18 1.3813(14) . ? O4 C18 1.3479(15) . ? O4 C21 1.4312(15) . ? F1 C2 1.3444(18) . ? F2 C3 1.3439(19) . ? F3 C4 1.3405(17) . ? F4 C5 1.3417(18) . ? F5 C6 1.3465(16) . ? F6 C13 1.3443(14) . ? F7 C14 1.3409(15) . ? F8 C15 1.3409(14) . ? F9 C16 1.3415(14) . ? F10 C17 1.3349(14) . ? F11 C24 1.3420(14) . ? F12 C25 1.3413(15) . ? F13 C26 1.3352(14) . ? F14 C27 1.3414(14) . ? F15 C28 1.3434(14) . ? C1 C6 1.3820(18) . ? C1 C2 1.3854(18) . ? C2 C3 1.380(2) . ? C3 C4 1.374(3) . ? C4 C5 1.375(3) . ? C5 C6 1.3810(18) . ? C7 C8 1.3289(17) . ? C8 C12 1.4869(16) . ? C8 C9 1.5043(17) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.502(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.3903(18) . ? C12 C17 1.3929(16) . ? C13 C14 1.3855(18) . ? C14 C15 1.3772(18) . ? C15 C16 1.3785(19) . ? C16 C17 1.3835(17) . ? C18 C19 1.3336(16) . ? C19 C23 1.4827(16) . ? C19 C20 1.5104(17) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.494(2) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.3914(17) . ? C23 C28 1.3971(16) . ? C24 C25 1.3791(18) . ? C25 C26 1.3813(18) . ? C26 C27 1.3827(18) . ? C27 C28 1.3797(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 O1 B1 O3 117.39(10) . . ? O1 B1 C1 126.08(10) . . ? O3 B1 C1 116.50(10) . . ? B1 O1 C7 128.25(9) . . ? C7 O2 C10 115.78(10) . . ? B1 O3 C18 120.94(9) . . ? C18 O4 C21 120.42(10) . . ? C6 C1 C2 116.53(11) . . ? C6 C1 B1 122.15(11) . . ? C2 C1 B1 121.22(11) . . ? F1 C2 C3 118.40(13) . . ? F1 C2 C1 119.15(12) . . ? C3 C2 C1 122.43(14) . . ? F2 C3 C4 120.10(14) . . ? F2 C3 C2 120.85(17) . . ? C4 C3 C2 119.05(14) . . ? F3 C4 C3 120.05(16) . . ? F3 C4 C5 119.47(17) . . ? C3 C4 C5 120.48(13) . . ? F4 C5 C4 120.21(14) . . ? F4 C5 C6 120.69(15) . . ? C4 C5 C6 119.10(14) . . ? F5 C6 C5 118.11(13) . . ? F5 C6 C1 119.51(11) . . ? C5 C6 C1 122.37(13) . . ? C8 C7 O2 123.90(10) . . ? C8 C7 O1 120.01(10) . . ? O2 C7 O1 116.10(10) . . ? C7 C8 C12 119.01(10) . . ? C7 C8 C9 122.43(11) . . ? C12 C8 C9 118.54(11) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O2 C10 C11 112.83(13) . . ? O2 C10 H10A 109.0 . . ? C11 C10 H10A 109.0 . . ? O2 C10 H10B 109.0 . . ? C11 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C17 116.22(11) . . ? C13 C12 C8 121.88(11) . . ? C17 C12 C8 121.84(11) . . ? F6 C13 C14 117.39(12) . . ? F6 C13 C12 119.79(11) . . ? C14 C13 C12 122.83(11) . . ? F7 C14 C15 120.36(12) . . ? F7 C14 C13 120.50(12) . . ? C15 C14 C13 119.12(12) . . ? F8 C15 C14 120.39(12) . . ? F8 C15 C16 119.71(11) . . ? C14 C15 C16 119.88(12) . . ? F9 C16 C15 119.72(11) . . ? F9 C16 C17 120.18(12) . . ? C15 C16 C17 120.08(11) . . ? F10 C17 C16 118.11(10) . . ? F10 C17 C12 120.02(11) . . ? C16 C17 C12 121.86(11) . . ? C19 C18 O4 121.56(11) . . ? C19 C18 O3 123.20(11) . . ? O4 C18 O3 115.13(10) . . ? C18 C19 C23 119.80(11) . . ? C18 C19 C20 121.14(11) . . ? C23 C19 C20 119.06(10) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O4 C21 C22 107.87(11) . . ? O4 C21 H21A 110.1 . . ? C22 C21 H21A 110.1 . . ? O4 C21 H21B 110.1 . . ? C22 C21 H21B 110.1 . . ? H21A C21 H21B 108.4 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C28 115.22(11) . . ? C24 C23 C19 123.15(11) . . ? C28 C23 C19 121.56(11) . . ? F11 C24 C25 117.20(11) . . ? F11 C24 C23 119.83(11) . . ? C25 C24 C23 122.96(11) . . ? F12 C25 C24 120.77(11) . . ? F12 C25 C26 119.18(12) . . ? C24 C25 C26 120.04(11) . . ? F13 C26 C25 120.40(11) . . ? F13 C26 C27 120.61(11) . . ? C25 C26 C27 118.98(11) . . ? F14 C27 C28 120.40(11) . . ? F14 C27 C26 119.72(11) . . ? C28 C27 C26 119.87(11) . . ? F15 C28 C27 117.38(11) . . ? F15 C28 C23 119.70(11) . . ? C27 C28 C23 122.92(11) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 32.06 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.403 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.049 data_rcn057_0m _database_code_depnum_ccdc_archive 'CCDC 892971' #TrackingRef 'All-cifs.txt' _audit_creation_method SHELXL-97 _chemical_formula_sum 'C19 H10 B F5 O' _chemical_formula_weight 360.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M R3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' _cell_length_a 20.7933(6) _cell_length_b 20.7933(6) _cell_length_c 9.7004(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3632.2(2) _cell_formula_units_Z 9 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7709 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 29.34 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.316 _exptl_crystal_size_mid 0.256 _exptl_crystal_size_min 0.213 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.482 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1638 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6644 _exptl_absorpt_correction_T_max 0.7461 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20296 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 30.52 _reflns_number_total 4878 _reflns_number_gt 4108 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0351P)^2^+1.1023P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.9(4) _refine_ls_number_reflns 4878 _refine_ls_number_parameters 275 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0500 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0780 _refine_ls_wR_factor_gt 0.0729 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.022 _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 F5 F 0.28000(5) 0.53133(5) 1.16291(8) 0.0308(2) Uani 1 1 d . . . C1 C 0.20900(7) 0.51073(7) 0.90808(12) 0.0182(2) Uani 1 1 d . . . F1 F 0.17694(6) 0.36639(5) 0.78483(10) 0.0371(2) Uani 1 1 d . . . C8 C 0.22959(7) 0.45496(7) 0.96620(13) 0.0211(3) Uani 1 1 d . . . C13 C 0.26287(8) 0.46782(8) 1.09536(14) 0.0255(3) Uani 1 1 d . . . F2 F 0.21191(6) 0.27362(5) 0.90785(13) 0.0502(3) Uani 1 1 d . . . C2 C 0.20721(7) 0.51257(7) 0.74837(12) 0.0206(3) Uani 1 1 d . . . C14 C 0.13474(8) 0.49115(8) 0.97698(13) 0.0232(3) Uani 1 1 d . . . C19 C 0.13049(9) 0.53321(9) 1.08405(14) 0.0263(3) Uani 1 1 d . . . C7 C 0.26602(8) 0.51619(8) 0.67234(14) 0.0269(3) Uani 1 1 d . . . C12 C 0.27793(10) 0.41823(10) 1.16225(15) 0.0352(4) Uani 1 1 d . . . C11 C 0.26012(10) 0.35269(10) 1.09881(19) 0.0391(4) Uani 1 1 d . . . F4 F 0.31015(7) 0.43438(7) 1.28671(10) 0.0520(3) Uani 1 1 d . . . C9 C 0.21174(8) 0.38708(8) 0.90731(15) 0.0271(3) Uani 1 1 d . . . C18 C 0.06359(9) 0.51159(10) 1.15103(18) 0.0366(4) Uani 1 1 d . . . F3 F 0.27479(8) 0.30365(7) 1.16059(13) 0.0633(4) Uani 1 1 d . . . C3 C 0.15296(9) 0.51991(9) 0.67839(14) 0.0284(3) Uani 1 1 d . . . C6 C 0.26941(9) 0.52595(9) 0.53034(15) 0.0345(4) Uani 1 1 d . . . C10 C 0.22753(9) 0.33703(8) 0.97131(18) 0.0337(4) Uani 1 1 d . . . C15 C 0.07012(9) 0.42603(9) 0.93943(17) 0.0335(4) Uani 1 1 d . . . C16 C 0.00348(10) 0.40515(11) 1.0064(2) 0.0457(4) Uani 1 1 d . . . C17 C -0.00009(10) 0.44762(11) 1.1122(2) 0.0443(4) Uani 1 1 d . . . C5 C 0.21425(11) 0.53181(9) 0.46209(15) 0.0364(4) Uani 1 1 d . . . C4 C 0.15613(11) 0.52846(10) 0.53590(16) 0.0366(4) Uani 1 1 d . . . O1 O 0.34762(5) 0.60914(5) 0.92703(9) 0.01820(18) Uani 1 1 d . . . B1 B 0.27500(8) 0.59427(8) 0.92628(13) 0.0178(3) Uani 1 1 d . . . H16 H -0.0410(13) 0.3609(13) 0.982(2) 0.056(6) Uiso 1 1 d . . . H3 H 0.1156(10) 0.5211(10) 0.7314(18) 0.034(5) Uiso 1 1 d . . . H15 H 0.0715(10) 0.3975(11) 0.8655(18) 0.034(5) Uiso 1 1 d . . . H7 H 0.3043(10) 0.5102(9) 0.7196(17) 0.030(4) Uiso 1 1 d . . . H17 H -0.0467(11) 0.4342(11) 1.161(2) 0.046(5) Uiso 1 1 d . . . H19 H 0.1746(10) 0.5781(10) 1.1076(17) 0.030(4) Uiso 1 1 d . . . H18 H 0.0614(10) 0.5437(11) 1.223(2) 0.041(5) Uiso 1 1 d . . . H6 H 0.3086(12) 0.5274(11) 0.482(2) 0.047(5) Uiso 1 1 d . . . H5 H 0.2193(10) 0.5383(10) 0.3650(19) 0.036(5) Uiso 1 1 d . . . H4 H 0.1158(12) 0.5300(11) 0.491(2) 0.048(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F5 0.0379(5) 0.0336(5) 0.0218(3) -0.0003(3) 0.0014(3) 0.0186(4) C1 0.0167(6) 0.0174(6) 0.0203(5) 0.0011(5) 0.0007(4) 0.0083(5) F1 0.0392(6) 0.0213(5) 0.0464(5) -0.0100(4) -0.0093(4) 0.0117(4) C8 0.0163(6) 0.0181(6) 0.0268(6) 0.0049(5) 0.0051(5) 0.0070(5) C13 0.0248(7) 0.0242(7) 0.0269(6) 0.0045(5) 0.0057(5) 0.0117(6) F2 0.0432(6) 0.0192(5) 0.0903(8) -0.0030(5) 0.0008(6) 0.0171(5) C2 0.0213(7) 0.0141(6) 0.0224(5) -0.0008(5) -0.0001(5) 0.0059(5) C14 0.0169(7) 0.0229(7) 0.0280(6) 0.0047(5) 0.0028(5) 0.0087(6) C19 0.0228(7) 0.0247(7) 0.0291(6) 0.0033(5) 0.0059(5) 0.0102(6) C7 0.0207(7) 0.0255(8) 0.0280(6) -0.0048(5) 0.0005(5) 0.0067(6) C12 0.0362(9) 0.0408(10) 0.0322(7) 0.0129(6) 0.0051(6) 0.0219(8) C11 0.0369(10) 0.0317(9) 0.0566(10) 0.0201(7) 0.0098(8) 0.0229(8) F4 0.0639(7) 0.0678(8) 0.0347(5) 0.0155(5) -0.0048(5) 0.0407(7) C9 0.0218(7) 0.0179(7) 0.0384(7) 0.0021(5) 0.0020(6) 0.0077(6) C18 0.0300(9) 0.0378(10) 0.0400(8) 0.0047(7) 0.0142(7) 0.0154(8) F3 0.0724(9) 0.0519(7) 0.0837(9) 0.0274(6) 0.0010(7) 0.0446(7) C3 0.0327(8) 0.0312(8) 0.0260(6) -0.0031(5) -0.0020(6) 0.0196(7) C6 0.0308(9) 0.0341(9) 0.0276(7) -0.0063(6) 0.0050(6) 0.0080(7) C10 0.0267(8) 0.0176(7) 0.0577(10) 0.0063(6) 0.0098(7) 0.0118(6) C15 0.0224(8) 0.0287(8) 0.0419(8) -0.0044(7) 0.0025(6) 0.0070(7) C16 0.0199(8) 0.0369(10) 0.0625(11) -0.0027(8) 0.0040(8) 0.0008(8) C17 0.0244(9) 0.0476(11) 0.0555(10) 0.0065(8) 0.0151(8) 0.0140(8) C5 0.0503(11) 0.0324(9) 0.0228(6) -0.0031(6) -0.0006(6) 0.0180(8) C4 0.0509(11) 0.0413(10) 0.0276(7) -0.0040(6) -0.0080(7) 0.0306(9) O1 0.0156(4) 0.0152(4) 0.0238(4) -0.0003(3) -0.0013(3) 0.0077(4) B1 0.0184(7) 0.0196(7) 0.0156(5) 0.0009(5) 0.0010(5) 0.0097(6) _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 F5 C13 1.3526(17) . ? C1 C8 1.5306(19) . ? C1 C14 1.5389(18) . ? C1 C2 1.5507(17) . ? C1 B1 1.596(2) . ? F1 C9 1.3450(18) . ? C8 C9 1.390(2) . ? C8 C13 1.3911(19) . ? C13 C12 1.380(2) . ? F2 C10 1.3396(19) . ? C2 C3 1.389(2) . ? C2 C7 1.397(2) . ? C14 C19 1.389(2) . ? C14 C15 1.397(2) . ? C19 C18 1.391(2) . ? C19 H19 0.953(19) . ? C7 C6 1.389(2) . ? C7 H7 0.978(18) . ? C12 F4 1.3395(19) . ? C12 C11 1.367(3) . ? C11 F3 1.3428(18) . ? C11 C10 1.369(3) . ? C9 C10 1.385(2) . ? C18 C17 1.380(3) . ? C18 H18 0.98(2) . ? C3 C4 1.391(2) . ? C3 H3 0.942(19) . ? C6 C5 1.381(3) . ? C6 H6 0.93(2) . ? C15 C16 1.389(2) . ? C15 H15 0.941(18) . ? C16 C17 1.379(3) . ? C16 H16 0.95(2) . ? C17 H17 0.99(2) . ? C5 C4 1.376(3) . ? C5 H5 0.950(18) . ? C4 H4 0.96(2) . ? O1 B1 1.3700(18) 2_665 ? O1 B1 1.3818(17) . ? B1 O1 1.3700(18) 3_565 ? 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 C8 C1 C14 105.27(10) . . ? C8 C1 C2 113.95(11) . . ? C14 C1 C2 114.02(11) . . ? C8 C1 B1 111.71(11) . . ? C14 C1 B1 116.28(11) . . ? C2 C1 B1 95.85(10) . . ? C9 C8 C13 114.83(12) . . ? C9 C8 C1 125.74(12) . . ? C13 C8 C1 119.13(12) . . ? F5 C13 C12 117.02(13) . . ? F5 C13 C8 119.13(12) . . ? C12 C13 C8 123.82(14) . . ? C3 C2 C7 118.23(12) . . ? C3 C2 C1 121.47(12) . . ? C7 C2 C1 119.83(12) . . ? C19 C14 C15 118.17(13) . . ? C19 C14 C1 121.98(13) . . ? C15 C14 C1 119.65(13) . . ? C14 C19 C18 120.94(15) . . ? C14 C19 H19 117.5(11) . . ? C18 C19 H19 121.5(10) . . ? C6 C7 C2 120.69(15) . . ? C6 C7 H7 119.9(10) . . ? C2 C7 H7 119.4(10) . . ? F4 C12 C11 120.53(15) . . ? F4 C12 C13 120.54(15) . . ? C11 C12 C13 118.92(15) . . ? F3 C11 C12 120.33(17) . . ? F3 C11 C10 119.73(17) . . ? C12 C11 C10 119.94(14) . . ? F1 C9 C10 116.57(13) . . ? F1 C9 C8 121.04(13) . . ? C10 C9 C8 122.38(14) . . ? C17 C18 C19 120.44(16) . . ? C17 C18 H18 120.0(11) . . ? C19 C18 H18 119.4(11) . . ? C2 C3 C4 120.71(15) . . ? C2 C3 H3 117.5(11) . . ? C4 C3 H3 121.7(11) . . ? C5 C6 C7 120.30(16) . . ? C5 C6 H6 120.6(12) . . ? C7 C6 H6 119.1(13) . . ? F2 C10 C11 119.79(15) . . ? F2 C10 C9 120.11(16) . . ? C11 C10 C9 120.09(15) . . ? C16 C15 C14 120.44(15) . . ? C16 C15 H15 120.0(12) . . ? C14 C15 H15 119.5(12) . . ? C17 C16 C15 120.83(16) . . ? C17 C16 H16 117.7(14) . . ? C15 C16 H16 121.5(14) . . ? C16 C17 C18 119.18(15) . . ? C16 C17 H17 122.4(12) . . ? C18 C17 H17 118.4(12) . . ? C4 C5 C6 119.53(14) . . ? C4 C5 H5 123.7(11) . . ? C6 C5 H5 116.7(11) . . ? C5 C4 C3 120.52(16) . . ? C5 C4 H4 121.4(12) . . ? C3 C4 H4 118.0(13) . . ? B1 O1 B1 120.97(12) 2_665 . ? O1 B1 O1 119.03(12) 3_565 . ? O1 B1 C1 121.11(12) 3_565 . ? O1 B1 C1 119.52(11) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.52 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.244 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.038 data_rcn064b_0m _database_code_depnum_ccdc_archive 'CCDC 892972' #TrackingRef 'All-cifs.txt' _audit_creation_method SHELXL-97 _chemical_formula_sum 'C57 H45 B3 O3' _chemical_formula_weight 810.36 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 9.5553(5) _cell_length_b 11.0517(6) _cell_length_c 21.8569(13) _cell_angle_alpha 92.454(4) _cell_angle_beta 97.710(4) _cell_angle_gamma 109.598(2) _cell_volume 2145.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7868 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 25.54 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.195 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 852 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6894 _exptl_absorpt_correction_T_max 0.7461 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 48640 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0623 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 30.69 _reflns_number_total 13141 _reflns_number_gt 8190 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0596P)^2^+0.2823P] 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 13141 _refine_ls_number_parameters 748 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1005 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1375 _refine_ls_wR_factor_gt 0.1180 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 O1 O 0.93046(11) 0.61403(9) 0.23768(4) 0.0225(2) Uani 1 1 d . . . O2 O 0.72585(11) 0.41772(9) 0.21323(4) 0.0255(2) Uani 1 1 d . . . O3 O 0.75100(11) 0.54951(9) 0.30468(4) 0.0271(2) Uani 1 1 d . . . C1 C 0.90209(16) 0.49811(12) 0.13010(6) 0.0209(3) Uani 1 1 d . . . C2 C 0.82429(16) 0.57860(13) 0.09073(6) 0.0222(3) Uani 1 1 d . . . C3 C 0.8385(2) 0.70271(15) 0.11369(7) 0.0355(4) Uani 1 1 d . . . C4 C 0.7693(3) 0.77615(18) 0.07999(8) 0.0456(5) Uani 1 1 d . . . C5 C 0.6852(2) 0.72763(17) 0.02212(8) 0.0380(4) Uani 1 1 d . . . C6 C 0.6748(2) 0.60723(16) -0.00228(8) 0.0362(4) Uani 1 1 d . . . C7 C 0.74302(18) 0.53335(15) 0.03194(7) 0.0289(3) Uani 1 1 d . . . C8 C 1.07384(16) 0.56059(13) 0.13720(6) 0.0228(3) Uani 1 1 d . . . C9 C 1.14524(18) 0.64354(14) 0.09606(7) 0.0293(3) Uani 1 1 d . . . C10 C 1.3018(2) 0.69103(16) 0.10166(8) 0.0382(4) Uani 1 1 d . . . C11 C 1.3887(2) 0.65784(17) 0.14888(8) 0.0396(4) Uani 1 1 d . . . C12 C 1.3198(2) 0.57690(17) 0.19107(8) 0.0370(4) Uani 1 1 d . . . C13 C 1.16444(18) 0.52859(15) 0.18499(7) 0.0296(3) Uani 1 1 d . . . C14 C 0.85181(17) 0.35761(13) 0.10037(6) 0.0232(3) Uani 1 1 d . . . C15 C 0.95126(19) 0.30877(15) 0.07582(7) 0.0300(3) Uani 1 1 d . . . C16 C 0.9025(2) 0.18365(16) 0.04635(8) 0.0390(4) Uani 1 1 d . . . C17 C 0.7537(2) 0.10552(15) 0.04132(7) 0.0375(4) Uani 1 1 d . . . C18 C 0.6530(2) 0.15204(15) 0.06586(7) 0.0342(4) Uani 1 1 d . . . C19 C 0.70165(19) 0.27679(14) 0.09495(7) 0.0282(3) Uani 1 1 d . . . C20 C 0.54156(16) 0.32646(13) 0.29189(6) 0.0231(3) Uani 1 1 d . . . C21 C 0.45443(16) 0.22208(13) 0.23852(6) 0.0247(3) Uani 1 1 d . . . C22 C 0.39449(18) 0.25885(15) 0.18332(7) 0.0302(3) Uani 1 1 d . . . C23 C 0.30461(19) 0.16797(17) 0.13592(7) 0.0355(4) Uani 1 1 d . . . C24 C 0.27406(19) 0.03708(17) 0.14162(8) 0.0367(4) Uani 1 1 d . . . C25 C 0.33306(18) -0.00079(16) 0.19560(8) 0.0329(3) Uani 1 1 d . . . C26 C 0.42130(17) 0.09068(14) 0.24382(7) 0.0283(3) Uani 1 1 d . . . C27 C 0.63168(16) 0.27559(13) 0.34267(6) 0.0241(3) Uani 1 1 d . . . C28 C 0.73774(17) 0.22429(14) 0.32626(8) 0.0291(3) Uani 1 1 d . . . C29 C 0.82252(19) 0.17933(15) 0.36965(8) 0.0359(4) Uani 1 1 d . . . C30 C 0.8072(2) 0.18733(16) 0.43144(8) 0.0397(4) Uani 1 1 d . . . C31 C 0.7044(2) 0.23938(17) 0.44946(8) 0.0401(4) Uani 1 1 d . . . C32 C 0.6173(2) 0.28271(15) 0.40524(7) 0.0329(3) Uani 1 1 d . . . C33 C 0.43224(17) 0.38175(14) 0.31956(6) 0.0257(3) Uani 1 1 d . . . C34 C 0.27696(18) 0.32005(17) 0.30469(7) 0.0339(4) Uani 1 1 d . . . C35 C 0.1774(2) 0.3692(2) 0.32852(8) 0.0420(4) Uani 1 1 d . . . C36 C 0.2299(2) 0.4802(2) 0.36865(9) 0.0444(5) Uani 1 1 d . . . C37 C 0.3837(2) 0.54030(17) 0.38601(8) 0.0391(4) Uani 1 1 d . . . C38 C 0.48337(19) 0.49232(15) 0.36157(7) 0.0313(3) Uani 1 1 d . . . C39 C 0.95468(15) 0.77218(12) 0.33375(6) 0.0192(3) Uani 1 1 d . . . C40 C 0.89015(15) 0.75903(13) 0.39507(6) 0.0221(3) Uani 1 1 d . . . C41 C 0.89633(17) 0.65729(15) 0.42988(7) 0.0280(3) Uani 1 1 d . . . C42 C 0.83946(19) 0.64047(18) 0.48529(7) 0.0355(4) Uani 1 1 d . . . C43 C 0.7765(2) 0.72622(18) 0.50751(7) 0.0391(4) Uani 1 1 d . . . C44 C 0.7730(2) 0.82859(18) 0.47454(7) 0.0382(4) Uani 1 1 d . . . C45 C 0.82880(18) 0.84518(15) 0.41858(7) 0.0306(3) Uani 1 1 d . . . C46 C 0.90052(16) 0.86219(13) 0.29157(6) 0.0216(3) Uani 1 1 d . . . C47 C 0.74728(17) 0.84042(14) 0.27624(7) 0.0272(3) Uani 1 1 d . . . C48 C 0.6947(2) 0.91625(16) 0.23701(7) 0.0336(4) Uani 1 1 d . . . C49 C 0.7954(2) 1.01399(16) 0.21062(7) 0.0352(4) Uani 1 1 d . . . C50 C 0.9466(2) 1.03448(16) 0.22387(7) 0.0346(4) Uani 1 1 d . . . C51 C 0.99939(18) 0.95980(14) 0.26422(7) 0.0280(3) Uani 1 1 d . . . C52 C 1.12737(16) 0.81995(13) 0.34956(6) 0.0217(3) Uani 1 1 d . . . C53 C 1.19913(19) 0.92086(18) 0.39599(8) 0.0392(4) Uani 1 1 d . . . C54 C 1.3538(2) 0.96756(19) 0.41192(8) 0.0442(5) Uani 1 1 d . . . C55 C 1.44207(18) 0.91560(17) 0.38232(8) 0.0358(4) Uani 1 1 d . . . C56 C 1.37288(19) 0.81776(16) 0.33603(9) 0.0383(4) Uani 1 1 d . . . C57 C 1.21728(18) 0.77065(15) 0.31983(8) 0.0319(3) Uani 1 1 d . . . B1 B 0.85012(18) 0.50744(14) 0.19641(7) 0.0206(3) Uani 1 1 d . . . B2 B 0.67545(19) 0.43611(15) 0.26812(7) 0.0225(3) Uani 1 1 d . . . B3 B 0.87921(18) 0.63881(14) 0.29113(7) 0.0198(3) Uani 1 1 d . . . H3 H 0.901(2) 0.7379(17) 0.1528(9) 0.043(5) Uiso 1 1 d . . . H4 H 0.787(2) 0.865(2) 0.0969(10) 0.067(6) Uiso 1 1 d . . . H5 H 0.633(2) 0.7730(19) -0.0002(9) 0.052(6) Uiso 1 1 d . . . H6 H 0.620(2) 0.5736(18) -0.0442(9) 0.047(5) Uiso 1 1 d . . . H7 H 0.7321(19) 0.4475(17) 0.0142(8) 0.037(5) Uiso 1 1 d . . . H9 H 1.0854(18) 0.6676(15) 0.0632(8) 0.029(4) Uiso 1 1 d . . . H10 H 1.350(2) 0.7504(17) 0.0732(8) 0.041(5) Uiso 1 1 d . . . H11 H 1.494(2) 0.6858(18) 0.1506(9) 0.046(5) Uiso 1 1 d . . . H12 H 1.385(2) 0.558(2) 0.2252(10) 0.062(6) Uiso 1 1 d . . . H13 H 1.114(2) 0.4665(17) 0.2146(8) 0.039(5) Uiso 1 1 d . . . H15 H 1.0588(19) 0.3613(15) 0.0791(7) 0.029(4) Uiso 1 1 d . . . H16 H 0.975(2) 0.1478(18) 0.0292(9) 0.050(5) Uiso 1 1 d . . . H17 H 0.722(2) 0.0193(19) 0.0214(9) 0.049(5) Uiso 1 1 d . . . H18 H 0.547(2) 0.0990(17) 0.0639(8) 0.038(5) Uiso 1 1 d . . . H19 H 0.628(2) 0.3092(16) 0.1110(8) 0.035(5) Uiso 1 1 d . . . H22 H 0.4168(19) 0.3512(17) 0.1800(8) 0.034(4) Uiso 1 1 d . . . H23 H 0.261(2) 0.1982(17) 0.0977(9) 0.045(5) Uiso 1 1 d . . . H24 H 0.201(2) -0.0266(16) 0.1086(8) 0.039(5) Uiso 1 1 d . . . H25 H 0.308(2) -0.0916(17) 0.1995(8) 0.037(5) Uiso 1 1 d . . . H26 H 0.461(2) 0.0617(16) 0.2831(8) 0.039(5) Uiso 1 1 d . . . H28 H 0.751(2) 0.2175(16) 0.2831(8) 0.038(5) Uiso 1 1 d . . . H29 H 0.898(2) 0.1397(18) 0.3554(9) 0.052(6) Uiso 1 1 d . . . H30 H 0.874(2) 0.1582(18) 0.4630(9) 0.047(5) Uiso 1 1 d . . . H31 H 0.6914(16) 0.2450(13) 0.4886(7) 0.011(3) Uiso 1 1 d . . . H32 H 0.543(2) 0.3196(18) 0.4185(8) 0.046(5) Uiso 1 1 d . . . H34 H 0.234(2) 0.2401(18) 0.2729(8) 0.044(5) Uiso 1 1 d . . . H35 H 0.066(2) 0.3204(18) 0.3176(9) 0.049(5) Uiso 1 1 d . . . H36 H 0.158(2) 0.5181(19) 0.3861(9) 0.053(6) Uiso 1 1 d . . . H37 H 0.424(2) 0.6185(18) 0.4157(8) 0.041(5) Uiso 1 1 d . . . H38 H 0.593(2) 0.5382(17) 0.3741(8) 0.037(5) Uiso 1 1 d . . . H41 H 0.9417(19) 0.5936(16) 0.4131(8) 0.036(5) Uiso 1 1 d . . . H42 H 0.845(2) 0.5714(17) 0.5075(8) 0.039(5) Uiso 1 1 d . . . H43 H 0.736(2) 0.7154(17) 0.5440(9) 0.044(5) Uiso 1 1 d . . . H44 H 0.730(2) 0.8857(18) 0.4875(9) 0.045(5) Uiso 1 1 d . . . H45 H 0.820(2) 0.9192(17) 0.3950(8) 0.038(5) Uiso 1 1 d . . . H47 H 0.672(2) 0.7726(16) 0.2932(8) 0.034(4) Uiso 1 1 d . . . H48 H 0.588(2) 0.8997(16) 0.2295(8) 0.038(5) Uiso 1 1 d . . . H49 H 0.763(2) 1.0655(18) 0.1820(9) 0.044(5) Uiso 1 1 d . . . H50 H 1.010(2) 1.1023(18) 0.2036(9) 0.046(5) Uiso 1 1 d . . . H51 H 1.107(2) 0.9767(16) 0.2716(7) 0.034(5) Uiso 1 1 d . . . H53 H 1.133(2) 0.9551(19) 0.4177(9) 0.058(6) Uiso 1 1 d . . . H54 H 1.404(2) 1.0414(19) 0.4440(10) 0.057(6) Uiso 1 1 d . . . H55 H 1.553(2) 0.9492(17) 0.3965(8) 0.040(5) Uiso 1 1 d . . . H56 H 1.429(2) 0.774(2) 0.3152(9) 0.059(6) Uiso 1 1 d . . . H57 H 1.168(2) 0.6996(19) 0.2873(9) 0.052(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0245(5) 0.0231(5) 0.0178(4) -0.0003(4) 0.0067(4) 0.0043(4) O2 0.0296(6) 0.0220(5) 0.0217(5) -0.0015(4) 0.0081(4) 0.0036(4) O3 0.0297(6) 0.0223(5) 0.0246(5) -0.0030(4) 0.0122(4) 0.0005(4) C1 0.0274(7) 0.0201(6) 0.0161(6) 0.0021(5) 0.0050(5) 0.0086(6) C2 0.0280(7) 0.0237(6) 0.0181(6) 0.0045(5) 0.0070(5) 0.0113(6) C3 0.0611(12) 0.0316(8) 0.0189(7) 0.0013(6) 0.0032(7) 0.0237(8) C4 0.0851(15) 0.0384(9) 0.0292(8) 0.0075(7) 0.0130(9) 0.0399(10) C5 0.0500(11) 0.0439(10) 0.0327(8) 0.0142(7) 0.0086(8) 0.0302(9) C6 0.0384(9) 0.0379(9) 0.0292(8) 0.0083(7) -0.0033(7) 0.0119(7) C7 0.0350(9) 0.0273(7) 0.0238(7) 0.0021(6) 0.0017(6) 0.0110(7) C8 0.0285(8) 0.0222(6) 0.0186(6) -0.0017(5) 0.0060(5) 0.0094(6) C9 0.0332(8) 0.0286(7) 0.0233(7) 0.0004(6) 0.0072(6) 0.0063(7) C10 0.0384(10) 0.0327(8) 0.0368(9) -0.0034(7) 0.0143(8) 0.0011(7) C11 0.0255(9) 0.0412(9) 0.0463(10) -0.0153(8) 0.0053(8) 0.0065(8) C12 0.0359(9) 0.0423(9) 0.0352(9) -0.0078(7) -0.0004(7) 0.0203(8) C13 0.0345(9) 0.0323(8) 0.0265(7) 0.0015(6) 0.0052(6) 0.0171(7) C14 0.0333(8) 0.0211(6) 0.0154(6) 0.0021(5) 0.0022(5) 0.0103(6) C15 0.0373(9) 0.0283(7) 0.0265(7) -0.0014(6) 0.0040(7) 0.0151(7) C16 0.0541(11) 0.0342(9) 0.0344(9) -0.0044(7) 0.0021(8) 0.0256(8) C17 0.0594(12) 0.0229(7) 0.0296(8) -0.0020(6) -0.0038(8) 0.0178(8) C18 0.0436(10) 0.0256(7) 0.0255(7) 0.0013(6) -0.0014(7) 0.0046(7) C19 0.0361(9) 0.0257(7) 0.0211(7) 0.0005(5) 0.0034(6) 0.0091(7) C20 0.0243(7) 0.0218(6) 0.0219(6) 0.0023(5) 0.0046(5) 0.0059(6) C21 0.0235(7) 0.0251(7) 0.0235(7) 0.0026(5) 0.0052(6) 0.0050(6) C22 0.0309(8) 0.0294(8) 0.0289(7) 0.0053(6) 0.0055(6) 0.0078(7) C23 0.0327(9) 0.0447(9) 0.0252(7) 0.0046(7) 0.0020(7) 0.0092(8) C24 0.0297(9) 0.0416(9) 0.0304(8) -0.0070(7) 0.0021(7) 0.0036(7) C25 0.0315(9) 0.0276(8) 0.0361(8) -0.0022(6) 0.0058(7) 0.0061(7) C26 0.0281(8) 0.0250(7) 0.0295(7) 0.0027(6) 0.0048(6) 0.0060(6) C27 0.0228(7) 0.0189(6) 0.0262(7) 0.0026(5) 0.0021(6) 0.0019(5) C28 0.0248(8) 0.0257(7) 0.0371(8) 0.0078(6) 0.0080(6) 0.0073(6) C29 0.0253(8) 0.0277(8) 0.0519(10) 0.0088(7) 0.0036(7) 0.0060(7) C30 0.0358(9) 0.0301(8) 0.0441(10) 0.0048(7) -0.0128(8) 0.0066(7) C31 0.0526(11) 0.0366(9) 0.0284(8) 0.0026(7) -0.0046(8) 0.0161(8) C32 0.0412(9) 0.0304(8) 0.0275(7) 0.0015(6) 0.0035(7) 0.0139(7) C33 0.0279(8) 0.0280(7) 0.0234(7) 0.0079(5) 0.0090(6) 0.0100(6) C34 0.0287(8) 0.0429(9) 0.0316(8) 0.0108(7) 0.0093(7) 0.0117(7) C35 0.0320(10) 0.0606(12) 0.0401(9) 0.0207(9) 0.0139(8) 0.0198(9) C36 0.0492(11) 0.0589(12) 0.0460(10) 0.0261(9) 0.0276(9) 0.0358(10) C37 0.0511(11) 0.0381(9) 0.0395(9) 0.0108(7) 0.0249(8) 0.0225(8) C38 0.0336(9) 0.0299(8) 0.0340(8) 0.0060(6) 0.0143(7) 0.0121(7) C39 0.0195(7) 0.0203(6) 0.0182(6) 0.0009(5) 0.0042(5) 0.0069(5) C40 0.0182(7) 0.0264(7) 0.0186(6) -0.0023(5) 0.0026(5) 0.0041(5) C41 0.0283(8) 0.0339(8) 0.0218(7) 0.0025(6) 0.0035(6) 0.0108(7) C42 0.0369(9) 0.0479(10) 0.0213(7) 0.0084(7) 0.0055(6) 0.0132(8) C43 0.0384(10) 0.0583(11) 0.0200(7) 0.0017(7) 0.0102(7) 0.0139(8) C44 0.0424(10) 0.0504(10) 0.0277(8) -0.0043(7) 0.0115(7) 0.0225(9) C45 0.0347(9) 0.0320(8) 0.0270(7) -0.0014(6) 0.0088(6) 0.0130(7) C46 0.0246(7) 0.0213(6) 0.0193(6) -0.0023(5) 0.0040(5) 0.0088(6) C47 0.0239(8) 0.0259(7) 0.0303(7) -0.0028(6) 0.0003(6) 0.0088(6) C48 0.0311(9) 0.0370(9) 0.0344(8) -0.0053(7) -0.0034(7) 0.0185(7) C49 0.0522(11) 0.0345(8) 0.0240(7) 0.0014(6) -0.0013(7) 0.0245(8) C50 0.0447(10) 0.0327(8) 0.0279(8) 0.0083(6) 0.0081(7) 0.0137(8) C51 0.0283(8) 0.0284(7) 0.0271(7) 0.0051(6) 0.0066(6) 0.0085(6) C52 0.0212(7) 0.0225(6) 0.0205(6) 0.0037(5) 0.0040(5) 0.0059(5) C53 0.0256(8) 0.0495(10) 0.0346(8) -0.0143(7) 0.0058(7) 0.0046(8) C54 0.0273(9) 0.0588(11) 0.0320(9) -0.0110(8) 0.0033(7) -0.0018(8) C55 0.0209(8) 0.0432(9) 0.0386(9) 0.0109(7) 0.0016(7) 0.0053(7) C56 0.0251(8) 0.0334(8) 0.0588(11) 0.0036(8) 0.0103(8) 0.0120(7) C57 0.0238(8) 0.0266(7) 0.0436(9) -0.0044(7) 0.0052(7) 0.0076(6) B1 0.0251(8) 0.0200(7) 0.0183(7) 0.0027(5) 0.0038(6) 0.0095(6) B2 0.0241(8) 0.0211(7) 0.0219(7) 0.0015(6) 0.0045(6) 0.0071(6) B3 0.0215(8) 0.0207(7) 0.0184(7) 0.0024(5) 0.0045(6) 0.0081(6) _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 O1 B3 1.3768(17) . ? O1 B1 1.3810(18) . ? O2 B1 1.3736(18) . ? O2 B2 1.3830(18) . ? O3 B3 1.3689(18) . ? O3 B2 1.3722(18) . ? C1 C8 1.535(2) . ? C1 C14 1.5472(18) . ? C1 C2 1.5563(19) . ? C1 B1 1.604(2) . ? C2 C7 1.386(2) . ? C2 C3 1.396(2) . ? C3 C4 1.385(2) . ? C3 H3 0.956(19) . ? C4 C5 1.383(3) . ? C4 H4 0.99(2) . ? C5 C6 1.379(2) . ? C5 H5 0.93(2) . ? C6 C7 1.389(2) . ? C6 H6 0.981(19) . ? C7 H7 0.976(18) . ? C8 C9 1.389(2) . ? C8 C13 1.400(2) . ? C9 C10 1.395(2) . ? C9 H9 0.960(16) . ? C10 C11 1.377(3) . ? C10 H10 0.970(18) . ? C11 C12 1.386(3) . ? C11 H11 0.94(2) . ? C12 C13 1.384(2) . ? C12 H12 0.98(2) . ? C13 H13 1.011(18) . ? C14 C15 1.392(2) . ? C14 C19 1.399(2) . ? C15 C16 1.398(2) . ? C15 H15 0.987(17) . ? C16 C17 1.380(3) . ? C16 H16 1.01(2) . ? C17 C18 1.388(3) . ? C17 H17 0.962(19) . ? C18 C19 1.392(2) . ? C18 H18 0.978(19) . ? C19 H19 0.983(18) . ? C20 C21 1.5378(19) . ? C20 C33 1.548(2) . ? C20 C27 1.5527(19) . ? C20 B2 1.602(2) . ? C21 C26 1.3922(19) . ? C21 C22 1.401(2) . ? C22 C23 1.383(2) . ? C22 H22 0.979(17) . ? C23 C24 1.391(2) . ? C23 H23 1.002(18) . ? C24 C25 1.381(2) . ? C24 H24 0.998(18) . ? C25 C26 1.394(2) . ? C25 H25 0.961(17) . ? C26 H26 1.002(18) . ? C27 C28 1.394(2) . ? C27 C32 1.394(2) . ? C28 C29 1.381(2) . ? C28 H28 0.971(18) . ? C29 C30 1.380(3) . ? C29 H29 1.03(2) . ? C30 C31 1.383(3) . ? C30 H30 1.012(19) . ? C31 C32 1.396(2) . ? C31 H31 0.883(14) . ? C32 H32 0.996(19) . ? C33 C34 1.395(2) . ? C33 C38 1.399(2) . ? C34 C35 1.388(2) . ? C34 H34 1.030(19) . ? C35 C36 1.379(3) . ? C35 H35 1.01(2) . ? C36 C37 1.385(3) . ? C36 H36 1.02(2) . ? C37 C38 1.387(2) . ? C37 H37 0.988(18) . ? C38 H38 0.991(18) . ? C39 C52 1.5388(19) . ? C39 C40 1.5414(18) . ? C39 C46 1.5502(19) . ? C39 B3 1.5968(19) . ? C40 C45 1.388(2) . ? C40 C41 1.397(2) . ? C41 C42 1.387(2) . ? C41 H41 1.021(17) . ? C42 C43 1.385(3) . ? C42 H42 0.934(18) . ? C43 C44 1.374(3) . ? C43 H43 0.925(19) . ? C44 C45 1.394(2) . ? C44 H44 0.914(19) . ? C45 H45 1.005(17) . ? C46 C51 1.392(2) . ? C46 C47 1.393(2) . ? C47 C48 1.385(2) . ? C47 H47 0.974(18) . ? C48 C49 1.389(2) . ? C48 H48 0.962(18) . ? C49 C50 1.373(2) . ? C49 H49 0.953(18) . ? C50 C51 1.391(2) . ? C50 H50 0.96(2) . ? C51 H51 0.975(18) . ? C52 C57 1.375(2) . ? C52 C53 1.395(2) . ? C53 C54 1.381(2) . ? C53 H53 1.00(2) . ? C54 C55 1.378(3) . ? C54 H54 0.99(2) . ? C55 C56 1.370(2) . ? C55 H55 1.002(18) . ? C56 C57 1.390(2) . ? C56 H56 0.98(2) . ? C57 H57 0.98(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 B3 O1 B1 121.48(11) . . ? B1 O2 B2 121.58(11) . . ? B3 O3 B2 122.54(11) . . ? C8 C1 C14 110.01(11) . . ? C8 C1 C2 110.39(11) . . ? C14 C1 C2 110.97(11) . . ? C8 C1 B1 109.28(11) . . ? C14 C1 B1 112.66(11) . . ? C2 C1 B1 103.35(11) . . ? C7 C2 C3 117.51(13) . . ? C7 C2 C1 122.46(12) . . ? C3 C2 C1 120.00(12) . . ? C4 C3 C2 121.31(15) . . ? C4 C3 H3 120.1(11) . . ? C2 C3 H3 118.5(11) . . ? C5 C4 C3 120.16(16) . . ? C5 C4 H4 120.9(12) . . ? C3 C4 H4 118.8(13) . . ? C6 C5 C4 119.30(15) . . ? C6 C5 H5 119.0(12) . . ? C4 C5 H5 121.6(12) . . ? C5 C6 C7 120.31(15) . . ? C5 C6 H6 120.2(11) . . ? C7 C6 H6 119.5(11) . . ? C2 C7 C6 121.33(15) . . ? C2 C7 H7 119.7(10) . . ? C6 C7 H7 119.0(10) . . ? C9 C8 C13 117.69(14) . . ? C9 C8 C1 122.79(13) . . ? C13 C8 C1 119.44(12) . . ? C8 C9 C10 120.93(15) . . ? C8 C9 H9 119.1(10) . . ? C10 C9 H9 119.9(10) . . ? C11 C10 C9 120.38(16) . . ? C11 C10 H10 119.6(11) . . ? C9 C10 H10 120.0(11) . . ? C10 C11 C12 119.65(17) . . ? C10 C11 H11 119.7(11) . . ? C12 C11 H11 120.6(11) . . ? C13 C12 C11 119.90(16) . . ? C13 C12 H12 122.5(13) . . ? C11 C12 H12 117.6(13) . . ? C12 C13 C8 121.45(15) . . ? C12 C13 H13 120.1(10) . . ? C8 C13 H13 118.4(10) . . ? C15 C14 C19 117.68(13) . . ? C15 C14 C1 121.82(13) . . ? C19 C14 C1 120.44(13) . . ? C14 C15 C16 121.15(16) . . ? C14 C15 H15 120.9(9) . . ? C16 C15 H15 118.0(9) . . ? C17 C16 C15 120.30(17) . . ? C17 C16 H16 118.7(11) . . ? C15 C16 H16 121.0(11) . . ? C16 C17 C18 119.46(15) . . ? C16 C17 H17 119.3(12) . . ? C18 C17 H17 121.2(12) . . ? C17 C18 C19 120.17(16) . . ? C17 C18 H18 121.8(10) . . ? C19 C18 H18 118.0(10) . . ? C18 C19 C14 121.25(15) . . ? C18 C19 H19 119.2(10) . . ? C14 C19 H19 119.6(10) . . ? C21 C20 C33 109.89(12) . . ? C21 C20 C27 112.18(11) . . ? C33 C20 C27 111.33(11) . . ? C21 C20 B2 110.09(11) . . ? C33 C20 B2 112.32(11) . . ? C27 C20 B2 100.79(11) . . ? C26 C21 C22 117.62(13) . . ? C26 C21 C20 123.19(12) . . ? C22 C21 C20 118.99(12) . . ? C23 C22 C21 121.26(15) . . ? C23 C22 H22 121.4(10) . . ? C21 C22 H22 117.3(10) . . ? C22 C23 C24 120.42(15) . . ? C22 C23 H23 118.8(11) . . ? C24 C23 H23 120.8(11) . . ? C25 C24 C23 119.04(15) . . ? C25 C24 H24 121.9(10) . . ? C23 C24 H24 118.7(10) . . ? C24 C25 C26 120.53(15) . . ? C24 C25 H25 118.2(10) . . ? C26 C25 H25 121.2(10) . . ? C21 C26 C25 121.11(14) . . ? C21 C26 H26 119.3(10) . . ? C25 C26 H26 119.6(10) . . ? C28 C27 C32 117.11(14) . . ? C28 C27 C20 119.24(13) . . ? C32 C27 C20 123.60(14) . . ? C29 C28 C27 121.70(15) . . ? C29 C28 H28 118.7(10) . . ? C27 C28 H28 119.6(10) . . ? C30 C29 C28 120.47(17) . . ? C30 C29 H29 120.2(11) . . ? C28 C29 H29 119.3(11) . . ? C29 C30 C31 119.33(16) . . ? C29 C30 H30 119.6(11) . . ? C31 C30 H30 121.1(11) . . ? C30 C31 C32 119.93(17) . . ? C30 C31 H31 121.4(9) . . ? C32 C31 H31 118.6(9) . . ? C27 C32 C31 121.44(16) . . ? C27 C32 H32 119.0(10) . . ? C31 C32 H32 119.5(11) . . ? C34 C33 C38 117.09(14) . . ? C34 C33 C20 120.73(13) . . ? C38 C33 C20 122.16(13) . . ? C35 C34 C33 121.44(17) . . ? C35 C34 H34 118.5(10) . . ? C33 C34 H34 119.9(10) . . ? C36 C35 C34 120.60(18) . . ? C36 C35 H35 120.4(11) . . ? C34 C35 H35 119.0(11) . . ? C35 C36 C37 118.97(17) . . ? C35 C36 H36 121.5(11) . . ? C37 C36 H36 119.5(11) . . ? C36 C37 C38 120.47(18) . . ? C36 C37 H37 120.4(11) . . ? C38 C37 H37 119.1(11) . . ? C37 C38 C33 121.36(16) . . ? C37 C38 H38 118.8(10) . . ? C33 C38 H38 119.8(10) . . ? C52 C39 C40 108.12(10) . . ? C52 C39 C46 111.44(10) . . ? C40 C39 C46 112.82(11) . . ? C52 C39 B3 115.65(11) . . ? C40 C39 B3 108.93(10) . . ? C46 C39 B3 99.81(10) . . ? C45 C40 C41 117.80(13) . . ? C45 C40 C39 123.35(12) . . ? C41 C40 C39 118.83(12) . . ? C42 C41 C40 121.31(15) . . ? C42 C41 H41 120.2(9) . . ? C40 C41 H41 118.5(9) . . ? C43 C42 C41 120.05(16) . . ? C43 C42 H42 120.5(11) . . ? C41 C42 H42 119.4(11) . . ? C44 C43 C42 119.27(15) . . ? C44 C43 H43 119.7(11) . . ? C42 C43 H43 121.1(11) . . ? C43 C44 C45 120.85(16) . . ? C43 C44 H44 121.4(12) . . ? C45 C44 H44 117.7(12) . . ? C40 C45 C44 120.69(15) . . ? C40 C45 H45 121.0(10) . . ? C44 C45 H45 118.3(10) . . ? C51 C46 C47 117.75(13) . . ? C51 C46 C39 122.24(13) . . ? C47 C46 C39 119.85(12) . . ? C48 C47 C46 121.39(15) . . ? C48 C47 H47 116.8(10) . . ? C46 C47 H47 121.8(10) . . ? C47 C48 C49 119.93(16) . . ? C47 C48 H48 118.1(10) . . ? C49 C48 H48 122.0(10) . . ? C50 C49 C48 119.44(15) . . ? C50 C49 H49 118.2(12) . . ? C48 C49 H49 122.3(12) . . ? C49 C50 C51 120.53(15) . . ? C49 C50 H50 115.5(11) . . ? C51 C50 H50 124.0(11) . . ? C50 C51 C46 120.92(15) . . ? C50 C51 H51 117.6(10) . . ? C46 C51 H51 121.4(10) . . ? C57 C52 C53 117.18(14) . . ? C57 C52 C39 123.95(12) . . ? C53 C52 C39 118.85(13) . . ? C54 C53 C52 121.21(16) . . ? C54 C53 H53 122.2(12) . . ? C52 C53 H53 116.5(12) . . ? C55 C54 C53 120.83(16) . . ? C55 C54 H54 118.6(12) . . ? C53 C54 H54 120.6(12) . . ? C56 C55 C54 118.43(16) . . ? C56 C55 H55 123.1(10) . . ? C54 C55 H55 118.5(10) . . ? C55 C56 C57 120.89(17) . . ? C55 C56 H56 121.9(12) . . ? C57 C56 H56 117.0(12) . . ? C52 C57 C56 121.44(15) . . ? C52 C57 H57 117.7(12) . . ? C56 C57 H57 120.9(12) . . ? O2 B1 O1 118.26(12) . . ? O2 B1 C1 123.35(12) . . ? O1 B1 C1 118.33(12) . . ? O3 B2 O2 117.73(13) . . ? O3 B2 C20 119.89(12) . . ? O2 B2 C20 122.23(12) . . ? O3 B3 O1 117.95(12) . . ? O3 B3 C39 119.39(12) . . ? O1 B3 C39 122.41(12) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 30.69 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.367 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.047 data_rcn060_C21H23BFNO2Si _database_code_depnum_ccdc_archive 'CCDC 892973' #TrackingRef 'All-cifs.txt' _audit_creation_method SHELXL-97 _chemical_formula_sum 'C21 H23 B F N O2 Si' _chemical_formula_weight 379.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3424(5) _cell_length_b 11.1791(8) _cell_length_c 22.4978(14) _cell_angle_alpha 76.520(4) _cell_angle_beta 82.063(3) _cell_angle_gamma 82.054(3) _cell_volume 2008.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5600 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 25.23 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.141 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6463 _exptl_absorpt_correction_T_max 0.7456 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32643 _diffrn_reflns_av_R_equivalents 0.0535 _diffrn_reflns_av_sigmaI/netI 0.0726 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.53 _reflns_number_total 9048 _reflns_number_gt 5663 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0366P)^2^+0.3730P] 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 9048 _refine_ls_number_parameters 577 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0961 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.0989 _refine_ls_wR_factor_gt 0.0856 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _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 Si1 Si 0.64375(6) 1.06586(5) 0.30982(2) 0.02603(14) Uani 1 1 d . . . Si2 Si 0.98772(6) 0.80179(5) 0.11502(3) 0.02771(14) Uani 1 1 d . . . O1 O 0.92151(15) 1.11881(12) 0.38978(6) 0.0286(3) Uani 1 1 d . . . O4 O 0.66522(14) 0.79452(11) 0.03796(5) 0.0250(3) Uani 1 1 d . . . O3 O 0.89452(14) 0.68131(12) -0.00472(6) 0.0266(3) Uani 1 1 d . . . F2 F 0.50277(14) 0.51258(11) 0.34014(5) 0.0418(3) Uani 1 1 d . . . O2 O 1.06444(15) 1.09703(12) 0.29448(6) 0.0294(3) Uani 1 1 d . . . N1 N 1.10715(17) 0.92453(14) 0.38680(7) 0.0242(4) Uani 1 1 d . . . F1 F 0.68183(18) 0.54324(12) 0.52100(6) 0.0628(4) Uani 1 1 d . . . C12 C 0.8311(2) 0.95947(17) 0.33478(8) 0.0221(4) Uani 1 1 d . . . H12 H 0.8789 0.9254 0.2981 0.027 Uiso 1 1 calc R . . C34 C 0.7758(2) 0.62556(17) 0.17315(8) 0.0238(4) Uani 1 1 d . . . C27 C 0.8220(2) 0.76688(17) -0.04983(9) 0.0237(4) Uani 1 1 d . . . C23 C 0.5901(3) 0.92313(18) -0.06133(9) 0.0293(5) Uani 1 1 d . . . C13 C 0.7857(2) 0.84853(17) 0.38390(8) 0.0227(4) Uani 1 1 d . . . C33 C 0.8766(2) 0.66670(17) 0.11251(8) 0.0235(4) Uani 1 1 d . . . H33 H 0.9641 0.5967 0.1098 0.028 Uiso 1 1 calc R . . C39 C 0.6239(2) 0.68807(18) 0.18784(9) 0.0263(4) Uani 1 1 d . . . C7 C 1.1576(2) 0.9371(2) 0.43866(10) 0.0322(5) Uani 1 1 d . . . C22 C 0.6850(2) 0.83264(17) -0.02503(8) 0.0242(4) Uani 1 1 d . . . C32 C 0.5155(2) 0.5750(2) 0.07812(10) 0.0314(5) Uani 1 1 d . . . C28 C 0.7559(3) 0.45193(19) 0.06103(9) 0.0288(5) Uani 1 1 d . . . C19 C 0.5039(2) 0.97060(19) 0.28842(9) 0.0351(5) Uani 1 1 d . . . H19A H 0.4042 1.0228 0.2764 0.053 Uiso 1 1 calc R . . H19B H 0.4764 0.9039 0.3237 0.053 Uiso 1 1 calc R . . H19C H 0.5575 0.9349 0.2539 0.053 Uiso 1 1 calc R . . C35 C 0.8314(2) 0.52456(18) 0.21723(9) 0.0287(5) Uani 1 1 d . . . C25 C 0.7764(3) 0.8865(2) -0.14912(10) 0.0352(5) Uani 1 1 d . . . C14 C 0.7527(2) 0.85603(19) 0.44560(9) 0.0259(4) Uani 1 1 d . . . C26 C 0.8706(2) 0.7924(2) -0.11195(9) 0.0308(5) Uani 1 1 d . . . C37 C 0.5928(2) 0.55040(19) 0.28482(9) 0.0292(5) Uani 1 1 d . . . C6 C 1.0089(2) 1.21726(18) 0.36477(10) 0.0296(5) Uani 1 1 d . . . C24 C 0.6386(3) 0.94917(19) -0.12435(10) 0.0341(5) Uani 1 1 d . . . C11 C 1.1615(2) 0.82159(19) 0.36592(10) 0.0295(5) Uani 1 1 d . . . C15 C 0.7186(2) 0.7542(2) 0.49173(10) 0.0316(5) Uani 1 1 d . . . C38 C 0.5316(2) 0.65112(19) 0.24367(9) 0.0298(5) Uani 1 1 d . . . B1 B 0.9710(3) 1.0302(2) 0.34937(10) 0.0257(5) Uani 1 1 d . . . C29 C 0.6760(3) 0.3480(2) 0.07569(9) 0.0342(5) Uani 1 1 d . . . C1 C 1.0924(2) 1.20460(18) 0.30834(9) 0.0302(5) Uani 1 1 d . . . C42 C 0.8452(2) 0.93978(19) 0.12641(10) 0.0392(5) Uani 1 1 d . . . H42A H 0.9075 1.0083 0.1258 0.059 Uiso 1 1 calc R . . H42B H 0.7787 0.9200 0.1661 0.059 Uiso 1 1 calc R . . H42C H 0.7743 0.9638 0.0933 0.059 Uiso 1 1 calc R . . C9 C 1.3141(3) 0.7404(2) 0.45063(11) 0.0383(6) Uani 1 1 d . . . C36 C 0.7411(2) 0.48673(19) 0.27323(9) 0.0329(5) Uani 1 1 d . . . H36 H 0.7815 0.4180 0.3030 0.039 Uiso 1 1 calc R . . C21 C 0.5349(2) 1.1392(2) 0.37249(9) 0.0390(6) Uani 1 1 d . . . H21A H 0.6045 1.1939 0.3825 0.059 Uiso 1 1 calc R . . H21B H 0.5087 1.0748 0.4090 0.059 Uiso 1 1 calc R . . H21C H 0.4341 1.1875 0.3589 0.059 Uiso 1 1 calc R . . C20 C 0.7035(3) 1.18657(19) 0.24110(9) 0.0382(5) Uani 1 1 d . . . H20A H 0.7478 1.1473 0.2068 0.057 Uiso 1 1 calc R . . H20B H 0.7864 1.2314 0.2506 0.057 Uiso 1 1 calc R . . H20C H 0.6078 1.2447 0.2297 0.057 Uiso 1 1 calc R . . C30 C 0.5100(3) 0.3592(2) 0.09252(10) 0.0375(5) Uani 1 1 d . . . B2 B 0.7843(2) 0.6844(2) 0.05236(10) 0.0239(5) Uani 1 1 d . . . C10 C 1.2637(2) 0.7280(2) 0.39682(11) 0.0351(5) Uani 1 1 d . . . C8 C 1.2614(3) 0.8469(2) 0.47144(11) 0.0406(6) Uani 1 1 d . . . C40 C 1.1134(3) 0.7534(2) 0.18132(10) 0.0451(6) Uani 1 1 d . . . H40A H 1.1723 0.8221 0.1834 0.068 Uiso 1 1 calc R . . H40B H 1.1917 0.6820 0.1755 0.068 Uiso 1 1 calc R . . H40C H 1.0421 0.7307 0.2197 0.068 Uiso 1 1 calc R . . C5 C 1.0183(3) 1.3178(2) 0.38886(11) 0.0409(6) Uani 1 1 d . . . H5 H 0.9615 1.3257 0.4276 0.049 Uiso 1 1 calc R . . C41 C 1.1255(2) 0.8434(2) 0.04277(10) 0.0396(5) Uani 1 1 d . . . H41A H 1.0605 0.8750 0.0082 0.059 Uiso 1 1 calc R . . H41B H 1.1976 0.7698 0.0358 0.059 Uiso 1 1 calc R . . H41C H 1.1910 0.9072 0.0463 0.059 Uiso 1 1 calc R . . C16 C 0.7169(3) 0.6440(2) 0.47580(10) 0.0369(5) Uani 1 1 d . . . C3 C 1.1956(3) 1.3955(2) 0.29841(14) 0.0518(7) Uani 1 1 d . . . C31 C 0.4295(3) 0.4746(2) 0.09278(10) 0.0401(6) Uani 1 1 d . . . H31 H 0.3148 0.4847 0.1031 0.048 Uiso 1 1 calc R . . C2 C 1.1869(2) 1.2932(2) 0.27359(11) 0.0400(6) Uani 1 1 d . . . H2 H 1.2433 1.2853 0.2348 0.048 Uiso 1 1 calc R . . C17 C 0.7461(3) 0.6307(2) 0.41602(11) 0.0380(5) Uani 1 1 d . . . C4 C 1.1140(3) 1.4078(2) 0.35445(13) 0.0517(7) Uani 1 1 d . . . H4 H 1.1230 1.4785 0.3699 0.062 Uiso 1 1 calc R . . N2 N 0.67706(17) 0.56489(14) 0.06249(7) 0.0230(4) Uani 1 1 d . . . C18 C 0.7797(2) 0.73403(19) 0.37059(10) 0.0301(5) Uani 1 1 d . . . H14 H 0.756(2) 0.9344(17) 0.4564(8) 0.020(5) Uiso 1 1 d . . . H39 H 0.582(2) 0.7594(17) 0.1594(8) 0.022(5) Uiso 1 1 d . . . H11 H 1.124(2) 0.8165(16) 0.3287(8) 0.022(5) Uiso 1 1 d . . . H35 H 0.939(2) 0.4783(17) 0.2087(8) 0.029(5) Uiso 1 1 d . . . H32 H 0.469(2) 0.6547(18) 0.0761(8) 0.027(5) Uiso 1 1 d . . . H24 H 0.575(2) 1.0139(18) -0.1509(9) 0.037(6) Uiso 1 1 d . . . H18 H 0.804(2) 0.7252(17) 0.3287(9) 0.030(5) Uiso 1 1 d . . . H26 H 0.965(2) 0.7460(17) -0.1277(8) 0.033(6) Uiso 1 1 d . . . H38 H 0.430(2) 0.6917(18) 0.2532(9) 0.034(6) Uiso 1 1 d . . . H25 H 0.806(2) 0.9036(19) -0.1897(10) 0.039(6) Uiso 1 1 d . . . H29 H 0.737(2) 0.2726(19) 0.0745(9) 0.034(6) Uiso 1 1 d . . . H28 H 0.869(2) 0.4499(17) 0.0490(9) 0.033(6) Uiso 1 1 d . . . H19 H 1.286(3) 0.859(2) 0.5086(11) 0.050(7) Uiso 1 1 d . . . H20 H 1.116(2) 1.0093(19) 0.4521(9) 0.037(6) Uiso 1 1 d . . . H15 H 0.694(2) 0.7606(18) 0.5327(9) 0.035(6) Uiso 1 1 d . . . H17 H 0.744(2) 0.555(2) 0.4067(9) 0.043(6) Uiso 1 1 d . . . H9 H 1.381(2) 0.673(2) 0.4747(9) 0.045(6) Uiso 1 1 d . . . H10 H 1.301(2) 0.653(2) 0.3812(9) 0.046(6) Uiso 1 1 d . . . H3 H 1.261(3) 1.450(2) 0.2741(11) 0.054(7) Uiso 1 1 d . . . H30 H 0.454(3) 0.286(2) 0.1024(10) 0.051(7) Uiso 1 1 d . . . H23 H 0.496(2) 0.9651(18) -0.0439(9) 0.032(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 Si1 0.0276(3) 0.0277(3) 0.0226(3) -0.0041(2) -0.0061(2) -0.0013(2) Si2 0.0240(3) 0.0305(3) 0.0294(3) -0.0050(3) -0.0055(2) -0.0056(2) O1 0.0279(7) 0.0260(8) 0.0349(8) -0.0122(6) -0.0041(6) -0.0025(6) O4 0.0270(7) 0.0261(8) 0.0213(7) -0.0060(6) -0.0047(5) 0.0027(6) O3 0.0220(7) 0.0307(8) 0.0247(7) -0.0039(6) -0.0011(5) 0.0002(6) F2 0.0504(7) 0.0459(8) 0.0273(7) -0.0043(6) 0.0037(6) -0.0138(6) O2 0.0295(7) 0.0279(8) 0.0304(8) -0.0040(6) -0.0001(6) -0.0090(6) N1 0.0208(8) 0.0259(9) 0.0265(9) -0.0068(7) -0.0011(7) -0.0044(7) F1 0.0952(11) 0.0396(8) 0.0487(9) 0.0131(7) -0.0126(8) -0.0244(8) C12 0.0240(10) 0.0233(10) 0.0200(10) -0.0073(8) -0.0016(8) -0.0021(8) C34 0.0255(10) 0.0226(11) 0.0260(11) -0.0071(9) -0.0087(8) -0.0034(8) C27 0.0224(10) 0.0246(11) 0.0259(11) -0.0061(9) -0.0027(8) -0.0071(8) C23 0.0366(12) 0.0255(12) 0.0279(12) -0.0090(9) -0.0100(9) 0.0012(9) C13 0.0186(9) 0.0244(11) 0.0257(11) -0.0061(9) -0.0055(8) -0.0009(8) C33 0.0192(9) 0.0216(10) 0.0291(11) -0.0054(8) -0.0042(8) 0.0008(8) C39 0.0268(10) 0.0243(11) 0.0278(11) -0.0037(9) -0.0079(9) -0.0010(8) C7 0.0335(12) 0.0304(13) 0.0358(13) -0.0097(10) -0.0110(9) -0.0022(10) C22 0.0286(10) 0.0235(11) 0.0236(11) -0.0073(9) -0.0059(8) -0.0069(8) C32 0.0254(11) 0.0343(13) 0.0374(13) -0.0130(10) -0.0052(9) -0.0023(10) C28 0.0301(12) 0.0295(12) 0.0274(11) -0.0078(9) -0.0041(9) -0.0022(9) C19 0.0299(11) 0.0397(13) 0.0357(13) -0.0034(10) -0.0106(9) -0.0052(9) C35 0.0278(11) 0.0275(12) 0.0303(12) -0.0051(9) -0.0077(9) 0.0011(9) C25 0.0453(13) 0.0394(14) 0.0228(12) -0.0027(10) -0.0042(10) -0.0177(11) C14 0.0237(10) 0.0260(12) 0.0290(12) -0.0069(10) -0.0053(8) -0.0014(8) C26 0.0281(11) 0.0352(13) 0.0299(12) -0.0074(10) 0.0021(9) -0.0105(9) C37 0.0354(11) 0.0344(12) 0.0207(11) -0.0065(9) -0.0016(9) -0.0143(9) C6 0.0289(11) 0.0197(11) 0.0425(13) -0.0039(10) -0.0191(9) -0.0005(9) C24 0.0476(14) 0.0255(12) 0.0307(13) -0.0010(10) -0.0156(10) -0.0068(10) C11 0.0266(11) 0.0308(12) 0.0332(13) -0.0122(10) -0.0007(9) -0.0033(9) C15 0.0313(11) 0.0369(13) 0.0257(12) -0.0038(10) -0.0052(9) -0.0034(9) C38 0.0256(11) 0.0339(13) 0.0320(12) -0.0117(10) -0.0033(9) -0.0025(9) B1 0.0255(12) 0.0256(13) 0.0262(13) -0.0061(10) -0.0042(9) -0.0011(9) C29 0.0468(14) 0.0284(13) 0.0296(12) -0.0080(10) -0.0098(10) -0.0034(11) C1 0.0261(10) 0.0278(12) 0.0376(13) -0.0013(10) -0.0144(9) -0.0047(9) C42 0.0389(12) 0.0336(13) 0.0487(14) -0.0145(11) -0.0015(10) -0.0101(10) C9 0.0296(12) 0.0338(13) 0.0485(15) 0.0003(11) -0.0110(10) -0.0021(10) C36 0.0424(13) 0.0272(12) 0.0279(12) 0.0003(9) -0.0122(10) -0.0021(10) C21 0.0342(12) 0.0469(14) 0.0353(13) -0.0119(11) -0.0109(9) 0.0101(10) C20 0.0488(13) 0.0300(12) 0.0342(13) 0.0005(10) -0.0089(10) -0.0067(10) C30 0.0476(14) 0.0371(14) 0.0332(13) -0.0072(11) -0.0082(10) -0.0202(12) B2 0.0207(11) 0.0240(12) 0.0269(12) -0.0063(10) -0.0020(9) -0.0014(9) C10 0.0291(11) 0.0284(13) 0.0465(15) -0.0094(11) -0.0001(10) -0.0006(9) C8 0.0425(13) 0.0452(15) 0.0371(14) -0.0100(12) -0.0175(11) -0.0003(11) C40 0.0446(13) 0.0474(15) 0.0473(15) -0.0044(12) -0.0197(11) -0.0138(11) C5 0.0431(13) 0.0295(13) 0.0557(15) -0.0114(11) -0.0264(11) 0.0008(10) C41 0.0346(12) 0.0449(14) 0.0416(14) -0.0102(11) -0.0006(10) -0.0145(10) C16 0.0414(12) 0.0289(13) 0.0365(13) 0.0076(10) -0.0102(10) -0.0099(10) C3 0.0482(15) 0.0337(15) 0.074(2) 0.0132(14) -0.0334(14) -0.0202(12) C31 0.0290(11) 0.0486(15) 0.0464(14) -0.0131(12) -0.0033(10) -0.0131(11) C2 0.0346(12) 0.0355(13) 0.0492(14) 0.0055(11) -0.0201(10) -0.0107(10) C17 0.0473(14) 0.0245(13) 0.0452(15) -0.0086(11) -0.0112(11) -0.0063(10) C4 0.0623(16) 0.0273(14) 0.073(2) -0.0065(13) -0.0391(15) -0.0059(12) N2 0.0218(8) 0.0265(9) 0.0219(9) -0.0076(7) -0.0045(6) -0.0008(7) C18 0.0330(11) 0.0298(12) 0.0291(12) -0.0081(10) -0.0057(9) -0.0040(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Si1 C20 1.860(2) . ? Si1 C21 1.861(2) . ? Si1 C19 1.861(2) . ? Si1 C12 1.8947(18) . ? Si2 C42 1.858(2) . ? Si2 C41 1.860(2) . ? Si2 C40 1.875(2) . ? Si2 C33 1.8933(19) . ? O1 C6 1.371(2) . ? O1 B1 1.477(3) . ? O4 C22 1.375(2) . ? O4 B2 1.474(2) . ? O3 C27 1.367(2) . ? O3 B2 1.477(2) . ? F2 C37 1.370(2) . ? O2 C1 1.368(2) . ? O2 B1 1.468(3) . ? N1 C7 1.337(2) . ? N1 C11 1.342(2) . ? N1 B1 1.680(3) . ? F1 C16 1.365(2) . ? C12 C13 1.509(2) . ? C12 B1 1.605(3) . ? C12 H12 1.0000 . ? C34 C35 1.390(3) . ? C34 C39 1.396(2) . ? C34 C33 1.509(3) . ? C27 C26 1.374(3) . ? C27 C22 1.393(3) . ? C23 C22 1.374(3) . ? C23 C24 1.393(3) . ? C23 H23 0.940(19) . ? C13 C18 1.390(3) . ? C13 C14 1.397(3) . ? C33 B2 1.608(3) . ? C33 H33 1.0000 . ? C39 C38 1.386(3) . ? C39 H39 0.956(17) . ? C7 C8 1.378(3) . ? C7 H20 0.93(2) . ? C32 N2 1.341(2) . ? C32 C31 1.367(3) . ? C32 H32 0.916(18) . ? C28 N2 1.346(2) . ? C28 C29 1.370(3) . ? C28 H28 0.945(19) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C35 C36 1.382(3) . ? C35 H35 0.990(18) . ? C25 C24 1.380(3) . ? C25 C26 1.402(3) . ? C25 H25 0.90(2) . ? C14 C15 1.383(3) . ? C14 H14 0.966(18) . ? C26 H26 0.957(18) . ? C37 C36 1.363(3) . ? C37 C38 1.368(3) . ? C6 C5 1.372(3) . ? C6 C1 1.389(3) . ? C24 H24 0.97(2) . ? C11 C10 1.372(3) . ? C11 H11 0.953(18) . ? C15 C16 1.363(3) . ? C15 H15 0.93(2) . ? C38 H38 0.930(19) . ? C29 C30 1.381(3) . ? C29 H29 0.926(19) . ? C1 C2 1.378(3) . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C9 C8 1.374(3) . ? C9 C10 1.377(3) . ? C9 H9 0.98(2) . ? C36 H36 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C30 C31 1.370(3) . ? C30 H30 0.96(2) . ? B2 N2 1.664(3) . ? C10 H10 0.98(2) . ? C8 H19 0.93(2) . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C5 C4 1.391(3) . ? C5 H5 0.9500 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C16 C17 1.372(3) . ? C3 C4 1.375(4) . ? C3 C2 1.399(3) . ? C3 H3 0.91(2) . ? C31 H31 0.9500 . ? C2 H2 0.9500 . ? C17 C18 1.385(3) . ? C17 H17 0.92(2) . ? C4 H4 0.9500 . ? C18 H18 0.961(19) . ? 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 C20 Si1 C21 110.29(10) . . ? C20 Si1 C19 108.82(10) . . ? C21 Si1 C19 108.50(10) . . ? C20 Si1 C12 109.46(9) . . ? C21 Si1 C12 112.09(9) . . ? C19 Si1 C12 107.59(9) . . ? C42 Si2 C41 109.39(10) . . ? C42 Si2 C40 108.24(11) . . ? C41 Si2 C40 108.75(10) . . ? C42 Si2 C33 112.14(9) . . ? C41 Si2 C33 110.10(9) . . ? C40 Si2 C33 108.14(9) . . ? C6 O1 B1 105.51(15) . . ? C22 O4 B2 105.39(14) . . ? C27 O3 B2 105.47(13) . . ? C1 O2 B1 105.92(15) . . ? C7 N1 C11 118.63(18) . . ? C7 N1 B1 121.88(16) . . ? C11 N1 B1 119.41(16) . . ? C13 C12 B1 115.20(15) . . ? C13 C12 Si1 111.29(11) . . ? B1 C12 Si1 113.67(13) . . ? C13 C12 H12 105.2 . . ? B1 C12 H12 105.2 . . ? Si1 C12 H12 105.2 . . ? C35 C34 C39 117.08(18) . . ? C35 C34 C33 121.32(16) . . ? C39 C34 C33 121.59(16) . . ? O3 C27 C26 127.99(17) . . ? O3 C27 C22 110.92(16) . . ? C26 C27 C22 121.08(18) . . ? C22 C23 C24 117.25(19) . . ? C22 C23 H23 120.8(12) . . ? C24 C23 H23 121.9(12) . . ? C18 C13 C14 116.93(18) . . ? C18 C13 C12 122.14(17) . . ? C14 C13 C12 120.90(17) . . ? C34 C33 B2 115.47(15) . . ? C34 C33 Si2 110.26(13) . . ? B2 C33 Si2 114.88(13) . . ? C34 C33 H33 105.0 . . ? B2 C33 H33 105.0 . . ? Si2 C33 H33 105.0 . . ? C38 C39 C34 121.74(18) . . ? C38 C39 H39 118.1(10) . . ? C34 C39 H39 120.1(10) . . ? N1 C7 C8 121.9(2) . . ? N1 C7 H20 116.2(12) . . ? C8 C7 H20 121.9(12) . . ? C23 C22 O4 127.70(17) . . ? C23 C22 C27 121.90(18) . . ? O4 C22 C27 110.39(15) . . ? N2 C32 C31 122.1(2) . . ? N2 C32 H32 114.1(12) . . ? C31 C32 H32 123.8(12) . . ? N2 C28 C29 121.8(2) . . ? N2 C28 H28 115.3(12) . . ? C29 C28 H28 122.9(12) . . ? Si1 C19 H19A 109.5 . . ? Si1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? Si1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C36 C35 C34 121.93(19) . . ? C36 C35 H35 118.6(10) . . ? C34 C35 H35 119.5(10) . . ? C24 C25 C26 121.2(2) . . ? C24 C25 H25 120.4(13) . . ? C26 C25 H25 118.3(13) . . ? C15 C14 C13 121.9(2) . . ? C15 C14 H14 119.1(10) . . ? C13 C14 H14 118.9(10) . . ? C27 C26 C25 117.3(2) . . ? C27 C26 H26 119.3(11) . . ? C25 C26 H26 123.4(11) . . ? C36 C37 C38 122.55(19) . . ? C36 C37 F2 118.55(18) . . ? C38 C37 F2 118.90(18) . . ? O1 C6 C5 127.8(2) . . ? O1 C6 C1 110.58(17) . . ? C5 C6 C1 121.6(2) . . ? C25 C24 C23 121.2(2) . . ? C25 C24 H24 120.0(12) . . ? C23 C24 H24 118.8(12) . . ? N1 C11 C10 122.1(2) . . ? N1 C11 H11 116.1(11) . . ? C10 C11 H11 121.8(11) . . ? C16 C15 C14 118.3(2) . . ? C16 C15 H15 120.4(13) . . ? C14 C15 H15 121.3(13) . . ? C37 C38 C39 118.23(19) . . ? C37 C38 H38 119.9(12) . . ? C39 C38 H38 121.8(12) . . ? O2 B1 O1 106.03(16) . . ? O2 B1 C12 114.21(16) . . ? O1 B1 C12 117.25(16) . . ? O2 B1 N1 105.60(14) . . ? O1 B1 N1 104.28(15) . . ? C12 B1 N1 108.44(15) . . ? C28 C29 C30 119.2(2) . . ? C28 C29 H29 118.1(13) . . ? C30 C29 H29 122.6(12) . . ? O2 C1 C2 127.8(2) . . ? O2 C1 C6 110.63(17) . . ? C2 C1 C6 121.5(2) . . ? Si2 C42 H42A 109.5 . . ? Si2 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? Si2 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C8 C9 C10 118.8(2) . . ? C8 C9 H9 120.6(13) . . ? C10 C9 H9 120.5(13) . . ? C37 C36 C35 118.46(18) . . ? C37 C36 H36 120.8 . . ? C35 C36 H36 120.8 . . ? Si1 C21 H21A 109.5 . . ? Si1 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? Si1 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? Si1 C20 H20A 109.5 . . ? Si1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? Si1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C31 C30 C29 118.9(2) . . ? C31 C30 H30 122.0(13) . . ? C29 C30 H30 119.1(13) . . ? O4 B2 O3 106.25(15) . . ? O4 B2 C33 117.80(16) . . ? O3 B2 C33 114.04(15) . . ? O4 B2 N2 104.75(14) . . ? O3 B2 N2 105.33(15) . . ? C33 B2 N2 107.61(15) . . ? C11 C10 C9 119.2(2) . . ? C11 C10 H10 121.1(13) . . ? C9 C10 H10 119.8(13) . . ? C9 C8 C7 119.3(2) . . ? C9 C8 H19 122.9(14) . . ? C7 C8 H19 117.6(14) . . ? Si2 C40 H40A 109.5 . . ? Si2 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? Si2 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C6 C5 C4 117.6(2) . . ? C6 C5 H5 121.2 . . ? C4 C5 H5 121.2 . . ? Si2 C41 H41A 109.5 . . ? Si2 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? Si2 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C15 C16 F1 118.7(2) . . ? C15 C16 C17 122.7(2) . . ? F1 C16 C17 118.6(2) . . ? C4 C3 C2 122.0(2) . . ? C4 C3 H3 124.9(15) . . ? C2 C3 H3 113.0(15) . . ? C32 C31 C30 119.5(2) . . ? C32 C31 H31 120.3 . . ? C30 C31 H31 120.3 . . ? C1 C2 C3 116.5(2) . . ? C1 C2 H2 121.7 . . ? C3 C2 H2 121.7 . . ? C16 C17 C18 118.0(2) . . ? C16 C17 H17 120.6(13) . . ? C18 C17 H17 121.4(13) . . ? C3 C4 C5 120.8(2) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C32 N2 C28 118.51(18) . . ? C32 N2 B2 121.93(16) . . ? C28 N2 B2 119.23(15) . . ? C17 C18 C13 122.2(2) . . ? C17 C18 H18 118.6(12) . . ? C13 C18 H18 119.2(12) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.339 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.047 data_C21H19BF5NO2Si _database_code_depnum_ccdc_archive 'CCDC 892974' #TrackingRef 'All-cifs.txt' _audit_creation_method SHELXL-97 _chemical_formula_sum 'C21 H19 B F5 N O2 Si' _chemical_formula_weight 451.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3043(8) _cell_length_b 11.1169(10) _cell_length_c 12.0808(11) _cell_angle_alpha 94.495(4) _cell_angle_beta 107.005(4) _cell_angle_gamma 98.763(4) _cell_volume 1045.11(17) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4609 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 26.69 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.175 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6716 _exptl_absorpt_correction_T_max 0.7456 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18802 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 27.52 _reflns_number_total 4795 _reflns_number_gt 3443 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0926P)^2^+1.7160P] 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 4795 _refine_ls_number_parameters 319 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0961 _refine_ls_R_factor_gt 0.0691 _refine_ls_wR_factor_ref 0.1974 _refine_ls_wR_factor_gt 0.1795 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 Si1 Si 0.41608(12) 0.10829(8) 0.28075(8) 0.0316(2) Uani 1 1 d . . . F1 F -0.0277(2) 0.13578(19) 0.19527(17) 0.0400(5) Uani 1 1 d . . . F2 F -0.2376(3) 0.1853(3) -0.00311(19) 0.0597(7) Uani 1 1 d . . . F3 F -0.1195(3) 0.3505(3) -0.1270(2) 0.0614(7) Uani 1 1 d . . . F4 F 0.2145(4) 0.4654(2) -0.0528(2) 0.0598(7) Uani 1 1 d . . . F5 F 0.4268(3) 0.41660(19) 0.14626(18) 0.0443(5) Uani 1 1 d . . . O1 O 0.1551(3) 0.17055(18) 0.44027(17) 0.0261(5) Uani 1 1 d . . . O2 O 0.4064(3) 0.32123(19) 0.51449(18) 0.0267(5) Uani 1 1 d . . . N1 N 0.1429(3) 0.3828(2) 0.3889(2) 0.0216(5) Uani 1 1 d . . . C1 C 0.2071(4) 0.2750(3) 0.1795(2) 0.0234(6) Uani 1 1 d . . . C2 C 0.0381(4) 0.2173(3) 0.1361(3) 0.0332(7) Uani 1 1 d . . . C3 C -0.0732(4) 0.2400(4) 0.0347(3) 0.0430(9) Uani 1 1 d . . . C4 C -0.0116(5) 0.3257(4) -0.0290(3) 0.0436(9) Uani 1 1 d . . . C5 C 0.1551(5) 0.3833(3) 0.0078(3) 0.0417(9) Uani 1 1 d . . . C6 C 0.2640(5) 0.3568(3) 0.1130(3) 0.0356(7) Uani 1 1 d . . . C7 C 0.3257(4) 0.2544(3) 0.2959(3) 0.0262(6) Uani 1 1 d . . . H7 H 0.4273 0.3218 0.3119 0.031 Uiso 1 1 calc R . . C8 C 0.5961(5) 0.1151(3) 0.4170(3) 0.0424(9) Uani 1 1 d . . . H8A H 0.6528 0.0448 0.4112 0.064 Uiso 1 1 calc R . . H8B H 0.5517 0.1128 0.4837 0.064 Uiso 1 1 calc R . . H8C H 0.6787 0.1915 0.4278 0.064 Uiso 1 1 calc R . . C9 C 0.2561(5) -0.0360(3) 0.2593(4) 0.0436(9) Uani 1 1 d . . . H9A H 0.3112 -0.1071 0.2530 0.065 Uiso 1 1 calc R . . H9B H 0.1614 -0.0385 0.1876 0.065 Uiso 1 1 calc R . . H9C H 0.2117 -0.0382 0.3260 0.065 Uiso 1 1 calc R . . C10 C 0.5007(6) 0.1134(4) 0.1535(4) 0.0504(10) Uani 1 1 d . . . H10A H 0.5731 0.1937 0.1601 0.076 Uiso 1 1 calc R . . H10B H 0.4049 0.1005 0.0810 0.076 Uiso 1 1 calc R . . H10C H 0.5687 0.0488 0.1528 0.076 Uiso 1 1 calc R . . C11 C -0.0290(4) 0.3580(3) 0.3585(3) 0.0292(7) Uani 1 1 d . . . C12 C -0.1263(4) 0.4479(4) 0.3307(3) 0.0365(8) Uani 1 1 d . . . C13 C -0.0459(5) 0.5660(3) 0.3350(3) 0.0348(8) Uani 1 1 d . . . C14 C 0.1322(5) 0.5923(3) 0.3690(3) 0.0320(7) Uani 1 1 d . . . C15 C 0.2215(4) 0.4987(3) 0.3946(3) 0.0261(6) Uani 1 1 d . . . C16 C 0.3615(4) 0.2709(3) 0.6034(3) 0.0235(6) Uani 1 1 d . . . C17 C 0.4453(4) 0.2975(3) 0.7207(3) 0.0295(7) Uani 1 1 d . . . C18 C 0.3755(4) 0.2347(3) 0.7964(3) 0.0336(7) Uani 1 1 d . . . C19 C 0.2261(4) 0.1481(3) 0.7535(3) 0.0318(7) Uani 1 1 d . . . C20 C 0.1406(4) 0.1198(3) 0.6329(3) 0.0271(6) Uani 1 1 d . . . C21 C 0.2112(4) 0.1826(2) 0.5598(2) 0.0211(6) Uani 1 1 d . . . B1 B 0.2604(4) 0.2735(3) 0.4091(3) 0.0251(7) Uani 1 1 d . . . H17 H 0.541(5) 0.356(3) 0.747(3) 0.037(10) Uiso 1 1 d . . . H19 H 0.181(5) 0.107(3) 0.806(3) 0.036(10) Uiso 1 1 d . . . H15 H 0.333(5) 0.513(3) 0.415(3) 0.026(9) Uiso 1 1 d . . . H18 H 0.420(5) 0.258(3) 0.880(3) 0.034(9) Uiso 1 1 d . . . H11 H -0.070(5) 0.281(4) 0.361(3) 0.034(10) Uiso 1 1 d . . . H12 H -0.244(6) 0.425(4) 0.303(4) 0.050(12) Uiso 1 1 d . . . H14 H 0.184(5) 0.666(3) 0.373(3) 0.028(9) Uiso 1 1 d . . . H20 H 0.045(5) 0.063(4) 0.604(3) 0.041(10) Uiso 1 1 d . . . H13 H -0.110(5) 0.623(4) 0.314(4) 0.049(12) 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 Si1 0.0367(5) 0.0337(5) 0.0362(5) 0.0104(4) 0.0220(4) 0.0178(4) F1 0.0320(10) 0.0491(12) 0.0378(11) 0.0060(9) 0.0134(8) -0.0009(9) F2 0.0320(11) 0.098(2) 0.0388(12) 0.0015(12) 0.0018(9) 0.0028(12) F3 0.0574(15) 0.0876(19) 0.0386(12) 0.0201(12) 0.0044(11) 0.0258(14) F4 0.0738(17) 0.0613(15) 0.0479(13) 0.0175(11) 0.0221(12) 0.0114(13) F5 0.0437(12) 0.0435(12) 0.0460(12) 0.0104(9) 0.0187(10) -0.0024(10) O1 0.0334(11) 0.0223(10) 0.0224(10) 0.0017(8) 0.0095(9) 0.0038(9) O2 0.0214(10) 0.0305(11) 0.0325(11) 0.0109(9) 0.0125(9) 0.0058(8) N1 0.0214(12) 0.0254(12) 0.0225(11) 0.0051(9) 0.0111(9) 0.0080(10) C1 0.0252(14) 0.0244(14) 0.0242(14) 0.0007(11) 0.0115(11) 0.0091(12) C2 0.0332(17) 0.0376(18) 0.0309(16) 0.0010(13) 0.0133(13) 0.0078(14) C3 0.0294(17) 0.063(2) 0.0302(17) -0.0108(16) 0.0019(14) 0.0114(17) C4 0.053(2) 0.055(2) 0.0279(17) 0.0085(16) 0.0128(16) 0.0219(19) C5 0.059(2) 0.044(2) 0.0294(17) 0.0110(15) 0.0181(16) 0.0169(18) C6 0.0404(19) 0.0311(17) 0.0377(18) 0.0013(14) 0.0181(15) 0.0035(14) C7 0.0218(14) 0.0293(15) 0.0274(14) 0.0031(12) 0.0083(12) 0.0031(12) C8 0.0382(19) 0.041(2) 0.056(2) 0.0111(17) 0.0198(17) 0.0181(16) C9 0.042(2) 0.0383(19) 0.052(2) -0.0031(16) 0.0199(17) 0.0066(16) C10 0.066(3) 0.049(2) 0.059(2) 0.0149(19) 0.042(2) 0.030(2) C11 0.0244(15) 0.0315(17) 0.0343(16) 0.0004(13) 0.0134(13) 0.0065(13) C12 0.0245(16) 0.051(2) 0.0368(18) 0.0013(15) 0.0102(14) 0.0173(15) C13 0.045(2) 0.0403(19) 0.0275(15) 0.0057(14) 0.0130(14) 0.0279(16) C14 0.0452(19) 0.0267(17) 0.0289(16) 0.0070(13) 0.0157(14) 0.0115(15) C15 0.0262(16) 0.0276(15) 0.0267(15) 0.0051(12) 0.0106(12) 0.0061(12) C16 0.0192(13) 0.0217(14) 0.0342(15) 0.0070(12) 0.0115(12) 0.0089(11) C17 0.0206(14) 0.0270(16) 0.0367(17) 0.0035(13) 0.0024(12) 0.0052(12) C18 0.0359(18) 0.0372(18) 0.0267(16) 0.0036(13) 0.0045(13) 0.0146(14) C19 0.0384(18) 0.0328(17) 0.0315(16) 0.0114(13) 0.0174(14) 0.0119(14) C20 0.0303(16) 0.0210(14) 0.0326(16) 0.0036(12) 0.0153(13) 0.0016(13) C21 0.0261(14) 0.0164(13) 0.0237(13) 0.0021(10) 0.0104(11) 0.0077(11) B1 0.0293(17) 0.0248(16) 0.0287(16) 0.0065(13) 0.0159(14) 0.0120(14) _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 Si1 C8 1.859(4) . ? Si1 C9 1.868(4) . ? Si1 C10 1.869(4) . ? Si1 C7 1.907(3) . ? F1 C2 1.345(4) . ? F2 C3 1.335(4) . ? F3 C4 1.337(4) . ? F4 C5 1.338(4) . ? F5 C6 1.340(4) . ? O1 C21 1.371(3) . ? O1 B1 1.474(4) . ? O2 C16 1.368(4) . ? O2 B1 1.472(4) . ? N1 C15 1.340(4) . ? N1 C11 1.344(4) . ? N1 B1 1.660(4) . ? C1 C2 1.378(4) . ? C1 C6 1.378(4) . ? C1 C7 1.520(4) . ? C2 C3 1.369(5) . ? C3 C4 1.399(6) . ? C4 C5 1.360(6) . ? C5 C6 1.410(5) . ? C7 B1 1.623(4) . ? C7 H7 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.381(5) . ? C11 H11 0.88(4) . ? C12 C13 1.369(5) . ? C12 H12 0.92(4) . ? C13 C14 1.391(5) . ? C13 H13 0.89(4) . ? C14 C15 1.371(4) . ? C14 H14 0.86(4) . ? C15 H15 0.87(4) . ? C16 C17 1.370(4) . ? C16 C21 1.400(4) . ? C17 C18 1.395(5) . ? C17 H17 0.90(4) . ? C18 C19 1.384(5) . ? C18 H18 0.96(4) . ? C19 C20 1.407(5) . ? C19 H19 0.94(4) . ? C20 C21 1.373(4) . ? C20 H20 0.90(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 Si1 C9 110.11(18) . . ? C8 Si1 C10 109.49(19) . . ? C9 Si1 C10 109.8(2) . . ? C8 Si1 C7 106.16(15) . . ? C9 Si1 C7 113.83(15) . . ? C10 Si1 C7 107.36(16) . . ? C21 O1 B1 105.1(2) . . ? C16 O2 B1 105.0(2) . . ? C15 N1 C11 118.8(3) . . ? C15 N1 B1 118.7(2) . . ? C11 N1 B1 122.3(3) . . ? C2 C1 C6 116.4(3) . . ? C2 C1 C7 122.8(3) . . ? C6 C1 C7 120.7(3) . . ? F1 C2 C3 116.1(3) . . ? F1 C2 C1 120.3(3) . . ? C3 C2 C1 123.6(3) . . ? F2 C3 C2 122.2(4) . . ? F2 C3 C4 119.6(3) . . ? C2 C3 C4 118.2(3) . . ? F3 C4 C5 120.2(3) . . ? F3 C4 C3 118.9(4) . . ? C5 C4 C3 120.8(3) . . ? F4 C5 C4 121.0(3) . . ? F4 C5 C6 120.4(3) . . ? C4 C5 C6 118.6(3) . . ? F5 C6 C1 121.4(3) . . ? F5 C6 C5 116.4(3) . . ? C1 C6 C5 122.2(3) . . ? C1 C7 B1 117.0(2) . . ? C1 C7 Si1 111.1(2) . . ? B1 C7 Si1 115.1(2) . . ? C1 C7 H7 103.9 . . ? B1 C7 H7 103.9 . . ? Si1 C7 H7 103.9 . . ? Si1 C8 H8A 109.5 . . ? Si1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? Si1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? Si1 C9 H9A 109.5 . . ? Si1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? Si1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? Si1 C10 H10A 109.5 . . ? Si1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? Si1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 C12 121.9(3) . . ? N1 C11 H11 113(2) . . ? C12 C11 H11 125(2) . . ? C13 C12 C11 119.3(3) . . ? C13 C12 H12 122(3) . . ? C11 C12 H12 119(3) . . ? C12 C13 C14 118.9(3) . . ? C12 C13 H13 119(3) . . ? C14 C13 H13 122(3) . . ? C15 C14 C13 119.1(3) . . ? C15 C14 H14 121(2) . . ? C13 C14 H14 120(2) . . ? N1 C15 C14 122.1(3) . . ? N1 C15 H15 117(2) . . ? C14 C15 H15 121(2) . . ? O2 C16 C17 127.8(3) . . ? O2 C16 C21 110.9(2) . . ? C17 C16 C21 121.4(3) . . ? C16 C17 C18 118.0(3) . . ? C16 C17 H17 120(2) . . ? C18 C17 H17 122(2) . . ? C19 C18 C17 120.6(3) . . ? C19 C18 H18 118(2) . . ? C17 C18 H18 121(2) . . ? C18 C19 C20 121.5(3) . . ? C18 C19 H19 119(2) . . ? C20 C19 H19 119(2) . . ? C21 C20 C19 117.0(3) . . ? C21 C20 H20 121(3) . . ? C19 C20 H20 122(3) . . ? O1 C21 C20 128.3(3) . . ? O1 C21 C16 110.2(2) . . ? C20 C21 C16 121.5(3) . . ? O2 B1 O1 106.5(2) . . ? O2 B1 C7 110.5(2) . . ? O1 B1 C7 120.3(3) . . ? O2 B1 N1 105.6(2) . . ? O1 B1 N1 105.4(2) . . ? C7 B1 N1 107.5(2) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.353 _refine_diff_density_min -0.583 _refine_diff_density_rms 0.081 #===end