# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Matthias Tamm' _publ_contact_author_email MATTHIAS.TAMM@TU-BS.DE _publ_section_title ; Dehydrogenation reactivity of a frustrated carbene-borane Lewis pair ; loop_ _publ_author_name 'Matthias Tamm' 'Thomas Bannenberg' 'Constantin Daniliuc' 'Dirk Holschumacher' 'Cristian Hrib' ; P.G.Jones ; 'Christina Taouss' # Attachment 'final.cif.txt' data_chta01 _database_code_depnum_ccdc_archive 'CCDC 726525' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31.50 H26 B F15 N2' _chemical_formula_weight 728.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.490(3) _cell_length_b 15.6557(10) _cell_length_c 19.933(5) _cell_angle_alpha 90.00 _cell_angle_beta 115.478(9) _cell_angle_gamma 90.00 _cell_volume 6617.3(19) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 19048 _cell_measurement_theta_min 3.5012 _cell_measurement_theta_max 75.7269 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2952 _exptl_absorpt_coefficient_mu 1.294 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.56203 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.36 (release 29-09-2008 CrysAlis171 .NET) (compiled Sep 29 2008,12:11:20) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Oxford Diffraction Nova A' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 10.3543 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44985 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 76.23 _reflns_number_total 6851 _reflns_number_gt 5618 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.36 (release 29-09-2008 CrysAlis171 .NET) (compiled Sep 29 2008,12:11:20) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.36 (release 29-09-2008 CrysAlis171 .NET) (compiled Sep 29 2008,12:11:20) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.36 (release 29-09-2008 CrysAlis171 .NET) (compiled Sep 29 2008,12:11:20) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _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. A diffuse region of electron density was tentatively identified as a disordered pentane molecule, but could not be refined satisfactorily. For this reason, the program SQUEEZE (A.L. Spek, University of Utrecht, Netherlands) was used to remove mathematically the effects of the solvent. The quoted formula and derived parameters are based on half a molecule of pentane per asymmetric unit. ; # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.000 0.060 585 107 ' ' 2 1.000 0.500 0.200 585 107 ' ' _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^)+(0.0548P)^2^+1.1127P] 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 'rigid methyls, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6851 _refine_ls_number_parameters 430 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0410 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0942 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.29485(5) 0.44150(7) 0.34931(6) 0.0296(2) Uani 1 1 d . . . N2 N 0.37525(5) 0.36811(7) 0.42708(6) 0.0290(2) Uani 1 1 d . . . B B 0.31586(7) 0.42485(9) 0.22069(7) 0.0289(3) Uani 1 1 d . . . F1 F 0.27621(4) 0.42556(6) 0.06158(4) 0.03956(19) Uani 1 1 d . . . F2 F 0.18065(5) 0.34000(7) -0.04222(5) 0.0559(3) Uani 1 1 d . . . F3 F 0.10035(5) 0.24681(7) -0.00397(5) 0.0563(3) Uani 1 1 d . . . F4 F 0.12006(4) 0.23926(6) 0.13975(5) 0.0421(2) Uani 1 1 d . . . F5 F 0.21899(4) 0.31453(5) 0.24527(4) 0.03340(17) Uani 1 1 d . . . F6 F 0.22098(4) 0.55341(6) 0.10858(5) 0.0427(2) Uani 1 1 d . . . F7 F 0.24565(5) 0.71529(6) 0.09454(5) 0.0510(2) Uani 1 1 d . . . F8 F 0.36082(5) 0.78373(5) 0.18025(6) 0.0487(2) Uani 1 1 d . . . F9 F 0.45152(4) 0.68453(5) 0.28342(5) 0.0423(2) Uani 1 1 d . . . F10 F 0.42825(4) 0.52194(5) 0.30066(4) 0.03551(17) Uani 1 1 d . . . F11 F 0.40923(4) 0.47603(5) 0.15401(4) 0.03668(18) Uani 1 1 d . . . F12 F 0.47988(4) 0.37159(6) 0.12083(5) 0.03938(19) Uani 1 1 d . . . F13 F 0.48234(4) 0.20090(5) 0.14888(4) 0.03992(19) Uani 1 1 d . . . F14 F 0.40913(4) 0.13833(5) 0.21320(5) 0.03888(18) Uani 1 1 d . . . F15 F 0.33645(4) 0.24101(5) 0.24768(4) 0.03343(17) Uani 1 1 d . . . C1 C 0.32481(6) 0.41270(8) 0.41904(7) 0.0311(3) Uani 1 1 d . . . H1 H 0.3118 0.4228 0.4573 0.037 Uiso 1 1 calc R . . C2 C 0.32802(6) 0.41303(8) 0.30840(7) 0.0282(2) Uani 1 1 d . . . C3 C 0.37779(6) 0.36868(8) 0.35937(7) 0.0284(2) Uani 1 1 d . . . H3 H 0.4097 0.3419 0.3495 0.034 Uiso 1 1 calc R . . C4 C 0.42268(6) 0.32826(9) 0.49725(7) 0.0338(3) Uani 1 1 d . . . C5 C 0.43765(9) 0.23923(10) 0.47849(9) 0.0472(4) Uani 1 1 d . . . H5A H 0.3986 0.2060 0.4554 0.057 Uiso 1 1 calc R . . H5B H 0.4668 0.2107 0.5241 0.057 Uiso 1 1 calc R . . H5C H 0.4571 0.2438 0.4439 0.057 Uiso 1 1 calc R . . C6 C 0.39470(7) 0.32241(11) 0.55332(8) 0.0407(3) Uani 1 1 d . . . H6A H 0.3859 0.3800 0.5656 0.049 Uiso 1 1 calc R . . H6B H 0.4248 0.2941 0.5985 0.049 Uiso 1 1 calc R . . H6C H 0.3554 0.2894 0.5319 0.049 Uiso 1 1 calc R . . C7 C 0.48112(7) 0.38497(12) 0.52702(8) 0.0443(3) Uani 1 1 d . . . H7A H 0.4976 0.3898 0.4896 0.053 Uiso 1 1 calc R . . H7B H 0.5134 0.3597 0.5725 0.053 Uiso 1 1 calc R . . H7C H 0.4699 0.4419 0.5381 0.053 Uiso 1 1 calc R . . C8 C 0.24233(6) 0.50641(9) 0.33195(7) 0.0344(3) Uani 1 1 d . . . C9 C 0.20836(7) 0.48798(10) 0.38096(8) 0.0396(3) Uani 1 1 d . . . H9A H 0.1972 0.4273 0.3774 0.047 Uiso 1 1 calc R . . H9B H 0.1699 0.5226 0.3641 0.047 Uiso 1 1 calc R . . H9C H 0.2362 0.5023 0.4327 0.047 Uiso 1 1 calc R . . C10 C 0.27400(8) 0.59400(9) 0.35039(9) 0.0438(3) Uani 1 1 d . . . H10A H 0.3062 0.5943 0.4020 0.053 Uiso 1 1 calc R . . H10B H 0.2423 0.6378 0.3441 0.053 Uiso 1 1 calc R . . H10C H 0.2938 0.6061 0.3170 0.053 Uiso 1 1 calc R . . C11 C 0.19408(7) 0.50226(10) 0.25123(8) 0.0398(3) Uani 1 1 d . . . H11A H 0.2159 0.5022 0.2189 0.048 Uiso 1 1 calc R . . H11B H 0.1662 0.5520 0.2397 0.048 Uiso 1 1 calc R . . H11C H 0.1691 0.4499 0.2430 0.048 Uiso 1 1 calc R . . C21 C 0.25104(6) 0.37915(8) 0.15905(7) 0.0302(3) Uani 1 1 d . . . C22 C 0.21018(6) 0.32771(8) 0.17456(7) 0.0305(3) Uani 1 1 d . . . C23 C 0.15909(6) 0.28573(9) 0.12091(8) 0.0350(3) Uani 1 1 d . . . C24 C 0.14886(7) 0.28969(10) 0.04774(8) 0.0411(3) Uani 1 1 d . . . C25 C 0.18907(7) 0.33704(10) 0.02880(7) 0.0409(3) Uani 1 1 d . . . C26 C 0.23816(7) 0.38057(9) 0.08369(7) 0.0345(3) Uani 1 1 d . . . C31 C 0.32356(6) 0.52730(8) 0.20633(7) 0.0312(3) Uani 1 1 d . . . C32 C 0.27945(7) 0.58149(9) 0.15459(7) 0.0349(3) Uani 1 1 d . . . C33 C 0.29087(7) 0.66671(9) 0.14570(8) 0.0392(3) Uani 1 1 d . . . C34 C 0.34863(8) 0.70199(9) 0.18903(8) 0.0380(3) Uani 1 1 d . . . C35 C 0.39447(7) 0.65154(9) 0.24145(7) 0.0352(3) Uani 1 1 d . . . C36 C 0.38066(6) 0.56750(8) 0.24932(7) 0.0318(3) Uani 1 1 d . . . C41 C 0.37000(6) 0.36649(8) 0.20711(7) 0.0291(2) Uani 1 1 d . . . C42 C 0.40798(6) 0.39343(8) 0.17346(7) 0.0310(3) Uani 1 1 d . . . C43 C 0.44522(6) 0.33967(9) 0.15393(7) 0.0324(3) Uani 1 1 d . . . C44 C 0.44626(6) 0.25349(9) 0.16737(7) 0.0335(3) Uani 1 1 d . . . C45 C 0.40955(6) 0.22224(8) 0.20011(7) 0.0323(3) Uani 1 1 d . . . C46 C 0.37292(6) 0.27827(9) 0.21852(7) 0.0302(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0321(5) 0.0314(5) 0.0254(5) -0.0001(4) 0.0124(4) 0.0033(4) N2 0.0308(5) 0.0333(5) 0.0234(5) 0.0013(4) 0.0120(4) 0.0018(4) B 0.0311(7) 0.0326(7) 0.0220(6) 0.0006(5) 0.0104(5) -0.0004(5) F1 0.0426(4) 0.0511(5) 0.0242(3) 0.0020(3) 0.0137(3) -0.0119(3) F2 0.0663(6) 0.0749(6) 0.0212(4) -0.0035(4) 0.0137(4) -0.0290(5) F3 0.0567(6) 0.0719(6) 0.0283(4) -0.0048(4) 0.0071(4) -0.0316(5) F4 0.0376(4) 0.0535(5) 0.0326(4) 0.0034(3) 0.0127(3) -0.0133(3) F5 0.0347(4) 0.0433(4) 0.0230(3) 0.0011(3) 0.0132(3) -0.0040(3) F6 0.0392(4) 0.0465(5) 0.0339(4) 0.0080(3) 0.0077(3) 0.0033(3) F7 0.0601(6) 0.0449(5) 0.0480(5) 0.0184(4) 0.0233(5) 0.0158(4) F8 0.0730(6) 0.0310(4) 0.0585(5) 0.0049(4) 0.0437(5) 0.0004(4) F9 0.0492(5) 0.0399(4) 0.0437(5) -0.0076(3) 0.0255(4) -0.0130(3) F10 0.0353(4) 0.0374(4) 0.0292(4) 0.0006(3) 0.0094(3) -0.0034(3) F11 0.0451(4) 0.0354(4) 0.0359(4) 0.0016(3) 0.0234(4) -0.0033(3) F12 0.0368(4) 0.0526(5) 0.0343(4) -0.0031(3) 0.0206(3) -0.0049(3) F13 0.0366(4) 0.0485(5) 0.0337(4) -0.0073(3) 0.0142(3) 0.0058(3) F14 0.0431(4) 0.0315(4) 0.0395(4) -0.0046(3) 0.0153(4) -0.0008(3) F15 0.0376(4) 0.0333(4) 0.0320(4) -0.0009(3) 0.0174(3) -0.0050(3) C1 0.0361(6) 0.0345(6) 0.0242(6) -0.0007(5) 0.0142(5) 0.0029(5) C2 0.0298(6) 0.0296(6) 0.0253(6) -0.0014(4) 0.0121(5) -0.0015(4) C3 0.0297(6) 0.0343(6) 0.0224(5) -0.0010(5) 0.0124(5) -0.0002(5) C4 0.0348(7) 0.0422(7) 0.0236(6) 0.0058(5) 0.0117(5) 0.0074(5) C5 0.0610(10) 0.0455(8) 0.0363(7) 0.0099(6) 0.0220(7) 0.0174(7) C6 0.0425(8) 0.0534(8) 0.0278(6) 0.0080(6) 0.0165(6) 0.0055(6) C7 0.0371(7) 0.0638(9) 0.0288(6) 0.0044(6) 0.0112(6) -0.0008(6) C8 0.0365(7) 0.0347(7) 0.0317(6) 0.0000(5) 0.0143(6) 0.0086(5) C9 0.0428(8) 0.0439(7) 0.0350(7) 0.0000(6) 0.0196(6) 0.0106(6) C10 0.0471(8) 0.0344(7) 0.0455(8) 0.0002(6) 0.0159(7) 0.0055(6) C11 0.0373(7) 0.0478(8) 0.0320(7) 0.0013(6) 0.0128(6) 0.0107(6) C21 0.0316(6) 0.0337(6) 0.0233(6) 0.0012(5) 0.0098(5) 0.0014(5) C22 0.0327(6) 0.0359(6) 0.0220(5) 0.0014(5) 0.0108(5) 0.0016(5) C23 0.0337(7) 0.0394(7) 0.0297(6) 0.0028(5) 0.0116(5) -0.0055(5) C24 0.0402(8) 0.0471(8) 0.0267(6) -0.0021(6) 0.0058(6) -0.0132(6) C25 0.0459(8) 0.0508(8) 0.0218(6) 0.0006(6) 0.0107(6) -0.0098(6) C26 0.0366(7) 0.0391(7) 0.0263(6) 0.0027(5) 0.0121(5) -0.0062(5) C31 0.0367(7) 0.0343(6) 0.0238(5) 0.0004(5) 0.0141(5) 0.0007(5) C32 0.0377(7) 0.0384(7) 0.0285(6) 0.0030(5) 0.0142(6) 0.0025(5) C33 0.0494(8) 0.0385(7) 0.0357(7) 0.0096(6) 0.0240(6) 0.0101(6) C34 0.0564(9) 0.0302(6) 0.0397(7) 0.0015(5) 0.0322(7) 0.0010(6) C35 0.0447(7) 0.0367(7) 0.0313(6) -0.0046(5) 0.0232(6) -0.0051(5) C36 0.0378(7) 0.0333(6) 0.0260(6) -0.0001(5) 0.0154(5) 0.0002(5) C41 0.0303(6) 0.0349(6) 0.0204(5) -0.0017(4) 0.0094(5) -0.0031(5) C42 0.0338(6) 0.0341(6) 0.0239(5) -0.0008(5) 0.0112(5) -0.0027(5) C43 0.0300(6) 0.0439(7) 0.0236(5) -0.0023(5) 0.0119(5) -0.0038(5) C44 0.0300(6) 0.0440(7) 0.0236(6) -0.0061(5) 0.0086(5) 0.0023(5) C45 0.0342(7) 0.0326(6) 0.0247(6) -0.0047(5) 0.0077(5) -0.0028(5) C46 0.0307(6) 0.0361(6) 0.0226(5) -0.0026(5) 0.0103(5) -0.0050(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.3375(17) . ? N1 C2 1.4202(16) . ? N1 C8 1.5190(16) . ? N2 C1 1.3241(17) . ? N2 C3 1.3764(16) . ? N2 C4 1.4988(16) . ? B C21 1.6523(19) . ? B C31 1.6528(19) . ? B C2 1.6562(18) . ? B C41 1.6797(19) . ? F1 C26 1.3522(15) . ? F2 C25 1.3432(16) . ? F3 C24 1.3420(16) . ? F4 C23 1.3444(16) . ? F5 C22 1.3494(14) . ? F6 C32 1.3554(17) . ? F7 C33 1.3471(17) . ? F8 C34 1.3392(16) . ? F9 C35 1.3408(17) . ? F10 C36 1.3496(15) . ? F11 C42 1.3541(15) . ? F12 C43 1.3453(15) . ? F13 C44 1.3418(15) . ? F14 C45 1.3401(16) . ? F15 C46 1.3567(15) . ? C2 C3 1.3636(18) . ? C4 C5 1.523(2) . ? C4 C6 1.5235(19) . ? C4 C7 1.525(2) . ? C8 C11 1.5193(19) . ? C8 C10 1.528(2) . ? C8 C9 1.531(2) . ? C21 C22 1.3859(18) . ? C21 C26 1.3992(18) . ? C22 C23 1.3825(19) . ? C23 C24 1.374(2) . ? C24 C25 1.375(2) . ? C25 C26 1.381(2) . ? C31 C32 1.3920(19) . ? C31 C36 1.3930(19) . ? C32 C33 1.387(2) . ? C33 C34 1.372(2) . ? C34 C35 1.381(2) . ? C35 C36 1.3801(19) . ? C41 C42 1.3921(18) . ? C41 C46 1.3966(19) . ? C42 C43 1.3852(19) . ? C43 C44 1.374(2) . ? C44 C45 1.376(2) . ? C45 C46 1.3843(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 C1 N1 C2 108.52(10) . . ? C1 N1 C8 118.36(11) . . ? C2 N1 C8 132.18(11) . . ? C1 N2 C3 106.98(11) . . ? C1 N2 C4 126.84(11) . . ? C3 N2 C4 126.12(10) . . ? C21 B C31 115.21(10) . . ? C21 B C2 114.95(10) . . ? C31 B C2 108.01(10) . . ? C21 B C41 99.45(10) . . ? C31 B C41 110.68(10) . . ? C2 B C41 108.09(10) . . ? N2 C1 N1 110.29(11) . . ? C3 C2 N1 103.79(10) . . ? C3 C2 B 123.13(11) . . ? N1 C2 B 133.08(11) . . ? C2 C3 N2 110.42(11) . . ? N2 C4 C5 108.02(11) . . ? N2 C4 C6 109.12(11) . . ? C5 C4 C6 110.07(12) . . ? N2 C4 C7 107.71(11) . . ? C5 C4 C7 111.35(13) . . ? C6 C4 C7 110.48(12) . . ? N1 C8 C11 112.05(11) . . ? N1 C8 C10 106.38(11) . . ? C11 C8 C10 110.94(12) . . ? N1 C8 C9 108.88(11) . . ? C11 C8 C9 108.15(12) . . ? C10 C8 C9 110.43(12) . . ? C22 C21 C26 113.46(12) . . ? C22 C21 B 126.22(11) . . ? C26 C21 B 119.72(11) . . ? F5 C22 C23 115.31(11) . . ? F5 C22 C21 120.80(11) . . ? C23 C22 C21 123.89(12) . . ? F4 C23 C24 119.48(12) . . ? F4 C23 C22 120.69(12) . . ? C24 C23 C22 119.81(12) . . ? F3 C24 C23 119.73(13) . . ? F3 C24 C25 121.01(13) . . ? C23 C24 C25 119.25(13) . . ? F2 C25 C24 120.06(13) . . ? F2 C25 C26 120.81(13) . . ? C24 C25 C26 119.13(13) . . ? F1 C26 C25 116.28(11) . . ? F1 C26 C21 119.36(12) . . ? C25 C26 C21 124.34(12) . . ? C32 C31 C36 113.16(12) . . ? C32 C31 B 128.15(12) . . ? C36 C31 B 118.69(11) . . ? F6 C32 C33 114.90(12) . . ? F6 C32 C31 121.21(12) . . ? C33 C32 C31 123.89(13) . . ? F7 C33 C34 119.56(13) . . ? F7 C33 C32 120.45(14) . . ? C34 C33 C32 119.99(13) . . ? F8 C34 C33 120.76(13) . . ? F8 C34 C35 120.29(14) . . ? C33 C34 C35 118.94(13) . . ? F9 C35 C36 121.13(13) . . ? F9 C35 C34 119.77(12) . . ? C36 C35 C34 119.10(13) . . ? F10 C36 C35 115.56(12) . . ? F10 C36 C31 119.47(11) . . ? C35 C36 C31 124.89(13) . . ? C42 C41 C46 112.41(11) . . ? C42 C41 B 126.82(11) . . ? C46 C41 B 119.95(11) . . ? F11 C42 C43 113.92(11) . . ? F11 C42 C41 121.65(12) . . ? C43 C42 C41 124.37(12) . . ? F12 C43 C44 119.79(12) . . ? F12 C43 C42 120.05(12) . . ? C44 C43 C42 120.15(12) . . ? F13 C44 C43 120.62(12) . . ? F13 C44 C45 120.72(13) . . ? C43 C44 C45 118.66(12) . . ? F14 C45 C44 119.97(12) . . ? F14 C45 C46 120.80(12) . . ? C44 C45 C46 119.22(12) . . ? F15 C46 C45 114.84(12) . . ? F15 C46 C41 119.94(11) . . ? C45 C46 C41 125.18(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N2 C1 N1 0.22(15) . . . . ? C4 N2 C1 N1 177.31(12) . . . . ? C2 N1 C1 N2 0.44(15) . . . . ? C8 N1 C1 N2 -169.79(11) . . . . ? C1 N1 C2 C3 -0.91(14) . . . . ? C8 N1 C2 C3 167.47(13) . . . . ? C1 N1 C2 B 179.02(13) . . . . ? C8 N1 C2 B -12.6(2) . . . . ? C21 B C2 C3 115.21(13) . . . . ? C31 B C2 C3 -114.61(13) . . . . ? C41 B C2 C3 5.18(16) . . . . ? C21 B C2 N1 -64.71(18) . . . . ? C31 B C2 N1 65.47(17) . . . . ? C41 B C2 N1 -174.74(12) . . . . ? N1 C2 C3 N2 1.05(14) . . . . ? B C2 C3 N2 -178.89(11) . . . . ? C1 N2 C3 C2 -0.83(14) . . . . ? C4 N2 C3 C2 -177.95(12) . . . . ? C1 N2 C4 C5 136.99(14) . . . . ? C3 N2 C4 C5 -46.46(17) . . . . ? C1 N2 C4 C6 17.33(18) . . . . ? C3 N2 C4 C6 -166.11(12) . . . . ? C1 N2 C4 C7 -102.63(15) . . . . ? C3 N2 C4 C7 73.93(16) . . . . ? C1 N1 C8 C11 -153.05(13) . . . . ? C2 N1 C8 C11 39.49(19) . . . . ? C1 N1 C8 C10 85.55(14) . . . . ? C2 N1 C8 C10 -81.91(16) . . . . ? C1 N1 C8 C9 -33.46(16) . . . . ? C2 N1 C8 C9 159.08(13) . . . . ? C31 B C21 C22 -132.04(13) . . . . ? C2 B C21 C22 -5.46(18) . . . . ? C41 B C21 C22 109.67(14) . . . . ? C31 B C21 C26 57.39(16) . . . . ? C2 B C21 C26 -176.03(12) . . . . ? C41 B C21 C26 -60.90(14) . . . . ? C26 C21 C22 F5 175.17(12) . . . . ? B C21 C22 F5 4.1(2) . . . . ? C26 C21 C22 C23 -3.8(2) . . . . ? B C21 C22 C23 -174.91(13) . . . . ? F5 C22 C23 F4 3.35(19) . . . . ? C21 C22 C23 F4 -177.60(12) . . . . ? F5 C22 C23 C24 -175.03(13) . . . . ? C21 C22 C23 C24 4.0(2) . . . . ? F4 C23 C24 F3 -0.4(2) . . . . ? C22 C23 C24 F3 178.00(14) . . . . ? F4 C23 C24 C25 -179.75(14) . . . . ? C22 C23 C24 C25 -1.3(2) . . . . ? F3 C24 C25 F2 -0.9(3) . . . . ? C23 C24 C25 F2 178.44(15) . . . . ? F3 C24 C25 C26 179.62(15) . . . . ? C23 C24 C25 C26 -1.0(2) . . . . ? F2 C25 C26 F1 0.2(2) . . . . ? C24 C25 C26 F1 179.65(14) . . . . ? F2 C25 C26 C21 -178.42(14) . . . . ? C24 C25 C26 C21 1.1(2) . . . . ? C22 C21 C26 F1 -177.27(12) . . . . ? B C21 C26 F1 -5.55(19) . . . . ? C22 C21 C26 C25 1.3(2) . . . . ? B C21 C26 C25 173.01(14) . . . . ? C21 B C31 C32 8.18(18) . . . . ? C2 B C31 C32 -121.85(14) . . . . ? C41 B C31 C32 120.00(14) . . . . ? C21 B C31 C36 -171.04(11) . . . . ? C2 B C31 C36 58.93(14) . . . . ? C41 B C31 C36 -59.22(14) . . . . ? C36 C31 C32 F6 -179.22(11) . . . . ? B C31 C32 F6 1.5(2) . . . . ? C36 C31 C32 C33 0.64(19) . . . . ? B C31 C32 C33 -178.62(13) . . . . ? F6 C32 C33 F7 0.15(19) . . . . ? C31 C32 C33 F7 -179.71(12) . . . . ? F6 C32 C33 C34 -179.64(12) . . . . ? C31 C32 C33 C34 0.5(2) . . . . ? F7 C33 C34 F8 -1.0(2) . . . . ? C32 C33 C34 F8 178.78(12) . . . . ? F7 C33 C34 C35 179.76(12) . . . . ? C32 C33 C34 C35 -0.5(2) . . . . ? F8 C34 C35 F9 -0.36(19) . . . . ? C33 C34 C35 F9 178.88(12) . . . . ? F8 C34 C35 C36 -179.98(12) . . . . ? C33 C34 C35 C36 -0.75(19) . . . . ? F9 C35 C36 F10 -0.86(17) . . . . ? C34 C35 C36 F10 178.76(11) . . . . ? F9 C35 C36 C31 -177.55(12) . . . . ? C34 C35 C36 C31 2.1(2) . . . . ? C32 C31 C36 F10 -178.51(11) . . . . ? B C31 C36 F10 0.82(17) . . . . ? C32 C31 C36 C35 -1.94(19) . . . . ? B C31 C36 C35 177.39(12) . . . . ? C21 B C41 C42 108.54(13) . . . . ? C31 B C41 C42 -13.09(17) . . . . ? C2 B C41 C42 -131.18(13) . . . . ? C21 B C41 C46 -60.25(13) . . . . ? C31 B C41 C46 178.13(11) . . . . ? C2 B C41 C46 60.03(14) . . . . ? C46 C41 C42 F11 176.43(11) . . . . ? B C41 C42 F11 6.93(19) . . . . ? C46 C41 C42 C43 -0.66(18) . . . . ? B C41 C42 C43 -170.16(12) . . . . ? F11 C42 C43 F12 1.99(17) . . . . ? C41 C42 C43 F12 179.28(11) . . . . ? F11 C42 C43 C44 -177.14(11) . . . . ? C41 C42 C43 C44 0.1(2) . . . . ? F12 C43 C44 F13 1.09(18) . . . . ? C42 C43 C44 F13 -179.78(11) . . . . ? F12 C43 C44 C45 -178.89(11) . . . . ? C42 C43 C44 C45 0.25(19) . . . . ? F13 C44 C45 F14 -0.65(18) . . . . ? C43 C44 C45 F14 179.32(11) . . . . ? F13 C44 C45 C46 179.96(11) . . . . ? C43 C44 C45 C46 -0.07(18) . . . . ? F14 C45 C46 F15 -1.98(17) . . . . ? C44 C45 C46 F15 177.40(11) . . . . ? F14 C45 C46 C41 -179.92(11) . . . . ? C44 C45 C46 C41 -0.5(2) . . . . ? C42 C41 C46 F15 -176.98(10) . . . . ? B C41 C46 F15 -6.67(17) . . . . ? C42 C41 C46 C45 0.86(18) . . . . ? B C41 C46 C45 171.17(11) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 72.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.309 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.038 #===END data_dhol40 _database_code_depnum_ccdc_archive 'CCDC 726526' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H24 B F15 N2' _chemical_formula_weight 696.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.3321(4) _cell_length_b 9.7938(2) _cell_length_c 19.7688(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.959(2) _cell_angle_gamma 90.00 _cell_volume 2839.39(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11028 _cell_measurement_theta_min 2.0711 _cell_measurement_theta_max 29.1737 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.629 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.164 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.93075 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.36 (release 29-09-2008 CrysAlis171 .NET) (compiled Sep 29 2008,12:11:20) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur E' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 16.1419 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 53738 _diffrn_reflns_av_R_equivalents 0.0612 _diffrn_reflns_av_sigmaI/netI 0.0787 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 26.37 _reflns_number_total 5800 _reflns_number_gt 3357 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.36 (release 29-09-2008 CrysAlis171 .NET) (compiled Sep 29 2008,12:11:20) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.36 (release 29-09-2008 CrysAlis171 .NET) (compiled Sep 29 2008,12:11:20) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.36 (release 29-09-2008 CrysAlis171 .NET) (compiled Sep 29 2008,12:11:20) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens XP' _computing_publication_material SHELXL-97 _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^)+(0.0316P)^2^] 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 ; H1, H2 free refined but thermal parameter were fixed, rigid methyls, others riding ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5800 _refine_ls_number_parameters 436 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0707 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0661 _refine_ls_wR_factor_gt 0.0629 _refine_ls_goodness_of_fit_ref 0.803 _refine_ls_restrained_S_all 0.803 _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 B B 0.26140(15) 1.0658(2) 0.27248(11) 0.0171(5) Uani 1 1 d . . . H2 H 0.3245(11) 1.1073(14) 0.3165(8) 0.021 Uiso 1 1 d . . . N1 N 0.37321(10) 0.79841(14) 0.04982(7) 0.0170(3) Uani 1 1 d . . . N2 N 0.22975(10) 0.82146(14) -0.01287(7) 0.0166(3) Uani 1 1 d . . . F1 F 0.10585(7) 1.22207(10) 0.16794(5) 0.0290(3) Uani 1 1 d . . . F2 F 0.12074(8) 1.36800(10) 0.05970(5) 0.0337(3) Uani 1 1 d . . . F3 F 0.28136(8) 1.38105(10) 0.02764(5) 0.0338(3) Uani 1 1 d . . . F4 F 0.43019(8) 1.24476(10) 0.11094(6) 0.0332(3) Uani 1 1 d . . . F5 F 0.41574(7) 1.09267(10) 0.21862(5) 0.0266(3) Uani 1 1 d . . . F6 F 0.24307(7) 1.26773(10) 0.37749(5) 0.0298(3) Uani 1 1 d . . . F7 F 0.09855(8) 1.30799(10) 0.42326(6) 0.0364(3) Uani 1 1 d . . . F8 F -0.05722(8) 1.16242(10) 0.36875(6) 0.0343(3) Uani 1 1 d . . . F9 F -0.06486(7) 0.97206(10) 0.26701(6) 0.0302(3) Uani 1 1 d . . . F10 F 0.07987(7) 0.92787(10) 0.22069(5) 0.0274(3) Uani 1 1 d . . . F11 F 0.34460(7) 0.88543(10) 0.38999(5) 0.0276(3) Uani 1 1 d . . . F12 F 0.37608(8) 0.61866(10) 0.38525(5) 0.0364(3) Uani 1 1 d . . . F13 F 0.32370(8) 0.48200(10) 0.25950(6) 0.0356(3) Uani 1 1 d . . . F14 F 0.24374(7) 0.61984(9) 0.13879(5) 0.0269(3) Uani 1 1 d . . . F15 F 0.21462(7) 0.88718(9) 0.14129(5) 0.0256(3) Uani 1 1 d . . . C1 C 0.29573(13) 0.73652(19) 0.01799(9) 0.0159(4) Uani 1 1 d . . . H1 H 0.2901(11) 0.6363(17) 0.0198(8) 0.019 Uiso 1 1 d . . . C2 C 0.36083(13) 0.94306(17) 0.03945(10) 0.0238(5) Uani 1 1 d . . . H2A H 0.4019 0.9797 0.0134 0.029 Uiso 1 1 calc R . . H2B H 0.3734 0.9910 0.0854 0.029 Uiso 1 1 calc R . . C3 C 0.26422(13) 0.95959(17) -0.00230(9) 0.0233(5) Uani 1 1 d . . . H3A H 0.2305 1.0143 0.0240 0.028 Uiso 1 1 calc R . . H3B H 0.2592 1.0047 -0.0481 0.028 Uiso 1 1 calc R . . C4 C 0.46335(13) 0.73545(17) 0.08708(9) 0.0212(4) Uani 1 1 d . . . C5 C 0.45112(13) 0.58434(17) 0.09804(11) 0.0295(5) Uani 1 1 d . . . H5A H 0.4065 0.5718 0.1244 0.044 Uiso 1 1 calc R . . H5B H 0.5097 0.5446 0.1248 0.044 Uiso 1 1 calc R . . H5C H 0.4292 0.5390 0.0520 0.044 Uiso 1 1 calc R . . C6 C 0.52624(14) 0.7557(2) 0.04105(10) 0.0377(6) Uani 1 1 d . . . H6A H 0.4991 0.7134 -0.0053 0.057 Uiso 1 1 calc R . . H6B H 0.5854 0.7131 0.0638 0.057 Uiso 1 1 calc R . . H6C H 0.5348 0.8536 0.0349 0.057 Uiso 1 1 calc R . . C7 C 0.50047(14) 0.80799(19) 0.15731(10) 0.0326(5) Uani 1 1 d . . . H7A H 0.5057 0.9059 0.1491 0.049 Uiso 1 1 calc R . . H7B H 0.5607 0.7711 0.1821 0.049 Uiso 1 1 calc R . . H7C H 0.4590 0.7938 0.1862 0.049 Uiso 1 1 calc R . . C8 C 0.13320(12) 0.78767(17) -0.05243(9) 0.0200(4) Uani 1 1 d . . . C9 C 0.11816(13) 0.82610(19) -0.12958(9) 0.0278(5) Uani 1 1 d . . . H9A H 0.1305 0.9236 -0.1329 0.042 Uiso 1 1 calc R . . H9B H 0.0549 0.8066 -0.1565 0.042 Uiso 1 1 calc R . . H9C H 0.1594 0.7728 -0.1489 0.042 Uiso 1 1 calc R . . C10 C 0.11790(13) 0.63579(17) -0.04513(10) 0.0266(5) Uani 1 1 d . . . H10A H 0.1583 0.5839 -0.0659 0.040 Uiso 1 1 calc R . . H10B H 0.0543 0.6131 -0.0698 0.040 Uiso 1 1 calc R . . H10C H 0.1312 0.6123 0.0050 0.040 Uiso 1 1 calc R . . C11 C 0.07040(13) 0.86871(18) -0.01995(10) 0.0239(5) Uani 1 1 d . . . H11A H 0.0829 0.8440 0.0300 0.036 Uiso 1 1 calc R . . H11B H 0.0067 0.8476 -0.0452 0.036 Uiso 1 1 calc R . . H11C H 0.0813 0.9666 -0.0238 0.036 Uiso 1 1 calc R . . C12 C 0.26070(13) 1.15089(16) 0.20112(9) 0.0174(4) Uani 1 1 d . . . C13 C 0.18906(13) 1.22375(17) 0.15696(9) 0.0188(4) Uani 1 1 d . . . C14 C 0.19455(14) 1.30021(17) 0.09994(9) 0.0223(5) Uani 1 1 d . . . C15 C 0.27518(14) 1.30825(18) 0.08358(10) 0.0229(5) Uani 1 1 d . . . C16 C 0.34950(14) 1.23949(18) 0.12571(10) 0.0213(5) Uani 1 1 d . . . C17 C 0.34026(13) 1.16273(17) 0.18139(9) 0.0195(4) Uani 1 1 d . . . C18 C 0.17045(12) 1.09185(16) 0.29799(9) 0.0159(4) Uani 1 1 d . . . C19 C 0.16846(13) 1.18849(17) 0.34862(9) 0.0197(4) Uani 1 1 d . . . C20 C 0.09458(14) 1.21336(17) 0.37309(10) 0.0204(4) Uani 1 1 d . . . C21 C 0.01542(13) 1.14060(18) 0.34535(10) 0.0221(5) Uani 1 1 d . . . C22 C 0.01267(13) 1.04421(18) 0.29468(9) 0.0195(4) Uani 1 1 d . . . C23 C 0.08855(13) 1.02228(17) 0.27231(9) 0.0177(4) Uani 1 1 d . . . C24 C 0.27899(12) 0.90215(17) 0.26581(9) 0.0160(4) Uani 1 1 d . . . C25 C 0.32002(12) 0.82472(18) 0.32528(9) 0.0189(4) Uani 1 1 d . . . C26 C 0.33643(13) 0.68698(19) 0.32468(10) 0.0227(5) Uani 1 1 d . . . C27 C 0.31045(13) 0.61673(18) 0.26175(10) 0.0223(5) Uani 1 1 d . . . C28 C 0.26940(12) 0.68737(18) 0.20096(9) 0.0189(4) Uani 1 1 d . . . C29 C 0.25543(12) 0.82570(17) 0.20406(9) 0.0172(4) 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 B 0.0143(13) 0.0211(12) 0.0159(12) -0.0020(9) 0.0044(10) -0.0026(10) N1 0.0124(9) 0.0177(8) 0.0191(8) 0.0007(7) 0.0019(7) 0.0002(7) N2 0.0147(9) 0.0160(8) 0.0172(8) 0.0007(6) 0.0016(7) 0.0017(7) F1 0.0171(7) 0.0386(7) 0.0306(6) 0.0098(5) 0.0058(5) 0.0010(5) F2 0.0290(7) 0.0345(6) 0.0332(7) 0.0127(5) 0.0024(6) 0.0002(5) F3 0.0394(8) 0.0368(6) 0.0267(6) 0.0080(5) 0.0120(6) -0.0075(6) F4 0.0294(8) 0.0381(6) 0.0395(7) 0.0016(6) 0.0215(6) -0.0032(5) F5 0.0195(7) 0.0322(6) 0.0300(6) 0.0011(5) 0.0102(5) 0.0052(5) F6 0.0234(7) 0.0287(6) 0.0381(7) -0.0153(5) 0.0100(6) -0.0072(5) F7 0.0358(8) 0.0370(7) 0.0421(7) -0.0156(6) 0.0200(6) 0.0020(6) F8 0.0253(7) 0.0414(7) 0.0432(7) 0.0036(6) 0.0207(6) 0.0061(6) F9 0.0161(7) 0.0365(6) 0.0360(7) 0.0019(5) 0.0046(5) -0.0069(5) F10 0.0215(7) 0.0320(6) 0.0268(6) -0.0115(5) 0.0040(5) -0.0058(5) F11 0.0332(8) 0.0323(6) 0.0147(6) -0.0010(5) 0.0029(5) -0.0019(5) F12 0.0440(8) 0.0326(6) 0.0257(7) 0.0117(5) -0.0004(6) 0.0074(6) F13 0.0405(8) 0.0219(6) 0.0399(7) -0.0004(5) 0.0044(6) 0.0079(5) F14 0.0311(7) 0.0261(6) 0.0232(6) -0.0085(5) 0.0075(5) 0.0002(5) F15 0.0329(7) 0.0248(6) 0.0149(6) 0.0012(5) 0.0002(5) 0.0017(5) C1 0.0183(12) 0.0176(10) 0.0130(9) -0.0003(8) 0.0065(8) 0.0005(9) C2 0.0247(13) 0.0192(11) 0.0270(11) 0.0004(9) 0.0067(10) -0.0003(9) C3 0.0295(13) 0.0190(11) 0.0216(11) 0.0010(8) 0.0076(9) -0.0003(9) C4 0.0123(11) 0.0274(11) 0.0220(11) 0.0013(9) 0.0018(9) 0.0028(9) C5 0.0135(12) 0.0250(11) 0.0448(14) 0.0013(9) 0.0003(10) 0.0064(9) C6 0.0211(13) 0.0579(14) 0.0366(13) 0.0136(11) 0.0123(11) 0.0071(11) C7 0.0257(13) 0.0352(12) 0.0277(12) -0.0002(9) -0.0065(10) 0.0027(10) C8 0.0129(11) 0.0281(11) 0.0163(10) -0.0020(8) 0.0000(8) 0.0008(9) C9 0.0158(12) 0.0477(12) 0.0179(11) 0.0018(9) 0.0019(9) 0.0057(10) C10 0.0164(12) 0.0281(12) 0.0293(11) -0.0064(9) -0.0025(9) -0.0001(9) C11 0.0194(12) 0.0297(11) 0.0229(11) -0.0002(9) 0.0066(9) 0.0033(9) C12 0.0173(12) 0.0150(10) 0.0196(10) -0.0055(8) 0.0050(9) -0.0035(8) C13 0.0122(11) 0.0234(11) 0.0216(10) -0.0022(8) 0.0060(9) -0.0040(9) C14 0.0229(13) 0.0195(10) 0.0204(11) 0.0020(9) -0.0002(9) -0.0001(9) C15 0.0314(13) 0.0177(10) 0.0215(11) 0.0023(9) 0.0106(10) -0.0071(10) C16 0.0229(13) 0.0214(10) 0.0249(11) -0.0065(9) 0.0154(10) -0.0064(9) C17 0.0187(12) 0.0187(10) 0.0203(11) -0.0035(8) 0.0045(9) 0.0024(9) C18 0.0162(11) 0.0156(10) 0.0146(10) 0.0014(8) 0.0025(8) 0.0004(8) C19 0.0139(11) 0.0212(10) 0.0217(10) 0.0001(9) 0.0018(9) -0.0022(9) C20 0.0248(13) 0.0152(10) 0.0224(10) -0.0036(8) 0.0086(9) 0.0017(9) C21 0.0194(12) 0.0254(11) 0.0266(11) 0.0083(9) 0.0146(9) 0.0096(9) C22 0.0128(12) 0.0225(10) 0.0205(11) 0.0057(9) 0.0006(9) -0.0036(9) C23 0.0218(12) 0.0179(10) 0.0125(10) -0.0001(8) 0.0037(9) 0.0008(9) C24 0.0088(10) 0.0224(10) 0.0181(10) -0.0007(8) 0.0062(8) -0.0019(8) C25 0.0150(11) 0.0287(12) 0.0133(10) -0.0042(8) 0.0044(8) -0.0030(9) C26 0.0226(12) 0.0248(11) 0.0196(11) 0.0074(9) 0.0044(9) 0.0040(9) C27 0.0191(12) 0.0158(11) 0.0326(12) 0.0016(9) 0.0084(9) 0.0043(9) C28 0.0171(11) 0.0236(11) 0.0169(10) -0.0047(9) 0.0064(9) -0.0032(9) C29 0.0143(11) 0.0217(11) 0.0153(10) 0.0049(8) 0.0039(8) 0.0024(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 B C18 1.635(3) . ? B C12 1.636(3) . ? B C24 1.637(3) . ? N1 C1 1.318(2) . ? N1 C2 1.436(2) . ? N1 C4 1.496(2) . ? N2 C1 1.314(2) . ? N2 C3 1.445(2) . ? N2 C8 1.496(2) . ? F1 C13 1.355(2) . ? F2 C14 1.352(2) . ? F3 C15 1.3422(19) . ? F4 C16 1.352(2) . ? F5 C17 1.362(2) . ? F6 C19 1.362(2) . ? F7 C20 1.3458(19) . ? F8 C21 1.342(2) . ? F9 C22 1.354(2) . ? F10 C23 1.3546(18) . ? F11 C25 1.3606(19) . ? F12 C26 1.351(2) . ? F13 C27 1.3378(19) . ? F14 C28 1.3493(19) . ? F15 C29 1.3568(19) . ? C2 C3 1.479(2) . ? C4 C7 1.515(2) . ? C4 C5 1.515(2) . ? C4 C6 1.520(3) . ? C8 C10 1.519(2) . ? C8 C9 1.522(2) . ? C8 C11 1.526(2) . ? C12 C13 1.385(2) . ? C12 C17 1.390(2) . ? C13 C14 1.376(2) . ? C14 C15 1.368(3) . ? C15 C16 1.375(3) . ? C16 C17 1.374(2) . ? C18 C19 1.384(2) . ? C18 C23 1.388(2) . ? C19 C20 1.377(2) . ? C20 C21 1.376(3) . ? C21 C22 1.368(2) . ? C22 C23 1.377(2) . ? C24 C25 1.386(2) . ? C24 C29 1.387(2) . ? C25 C26 1.373(2) . ? C26 C27 1.375(2) . ? C27 C28 1.370(2) . ? C28 C29 1.376(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 C18 B C12 113.26(15) . . ? C18 B C24 110.66(14) . . ? C12 B C24 112.90(15) . . ? C1 N1 C2 108.80(15) . . ? C1 N1 C4 128.30(14) . . ? C2 N1 C4 122.78(14) . . ? C1 N2 C3 109.01(15) . . ? C1 N2 C8 127.81(15) . . ? C3 N2 C8 123.17(14) . . ? N2 C1 N1 113.26(16) . . ? N1 C2 C3 104.88(14) . . ? N2 C3 C2 104.04(14) . . ? N1 C4 C7 107.70(14) . . ? N1 C4 C5 109.74(14) . . ? C7 C4 C5 110.86(15) . . ? N1 C4 C6 107.93(14) . . ? C7 C4 C6 110.69(16) . . ? C5 C4 C6 109.85(15) . . ? N2 C8 C10 108.88(14) . . ? N2 C8 C9 107.87(14) . . ? C10 C8 C9 110.78(15) . . ? N2 C8 C11 108.33(14) . . ? C10 C8 C11 109.60(15) . . ? C9 C8 C11 111.30(15) . . ? C13 C12 C17 112.32(16) . . ? C13 C12 B 127.63(17) . . ? C17 C12 B 119.94(16) . . ? F1 C13 C14 115.03(16) . . ? F1 C13 C12 120.22(16) . . ? C14 C13 C12 124.75(18) . . ? F2 C14 C15 119.43(16) . . ? F2 C14 C13 120.56(17) . . ? C15 C14 C13 120.01(18) . . ? F3 C15 C14 120.74(18) . . ? F3 C15 C16 120.92(18) . . ? C14 C15 C16 118.34(17) . . ? F4 C16 C17 120.56(17) . . ? F4 C16 C15 119.94(16) . . ? C17 C16 C15 119.48(18) . . ? F5 C17 C16 116.02(17) . . ? F5 C17 C12 118.90(16) . . ? C16 C17 C12 125.07(18) . . ? C19 C18 C23 113.05(16) . . ? C19 C18 B 122.02(16) . . ? C23 C18 B 124.92(15) . . ? F6 C19 C20 115.37(15) . . ? F6 C19 C18 119.96(16) . . ? C20 C19 C18 124.67(17) . . ? F7 C20 C21 119.70(17) . . ? F7 C20 C19 121.04(17) . . ? C21 C20 C19 119.26(16) . . ? F8 C21 C22 120.72(18) . . ? F8 C21 C20 120.29(17) . . ? C22 C21 C20 118.98(17) . . ? F9 C22 C21 119.48(17) . . ? F9 C22 C23 120.90(16) . . ? C21 C22 C23 119.63(17) . . ? F10 C23 C22 116.23(16) . . ? F10 C23 C18 119.35(16) . . ? C22 C23 C18 124.40(16) . . ? C25 C24 C29 112.85(15) . . ? C25 C24 B 120.80(16) . . ? C29 C24 B 126.34(16) . . ? F11 C25 C26 115.87(16) . . ? F11 C25 C24 119.41(15) . . ? C26 C25 C24 124.70(17) . . ? F12 C26 C25 121.00(17) . . ? F12 C26 C27 119.38(16) . . ? C25 C26 C27 119.60(17) . . ? F13 C27 C28 120.28(17) . . ? F13 C27 C26 121.13(16) . . ? C28 C27 C26 118.59(17) . . ? F14 C28 C27 119.25(16) . . ? F14 C28 C29 121.03(16) . . ? C27 C28 C29 119.72(17) . . ? F15 C29 C28 115.63(16) . . ? F15 C29 C24 119.84(15) . . ? C28 C29 C24 124.53(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N2 C1 N1 0.5(2) . . . . ? C8 N2 C1 N1 -178.81(15) . . . . ? C2 N1 C1 N2 -0.9(2) . . . . ? C4 N1 C1 N2 -176.79(15) . . . . ? C1 N1 C2 C3 0.9(2) . . . . ? C4 N1 C2 C3 177.08(15) . . . . ? C1 N2 C3 C2 0.13(19) . . . . ? C8 N2 C3 C2 179.43(15) . . . . ? N1 C2 C3 N2 -0.59(19) . . . . ? C1 N1 C4 C7 -132.99(18) . . . . ? C2 N1 C4 C7 51.6(2) . . . . ? C1 N1 C4 C5 -12.2(2) . . . . ? C2 N1 C4 C5 172.36(16) . . . . ? C1 N1 C4 C6 107.5(2) . . . . ? C2 N1 C4 C6 -67.9(2) . . . . ? C1 N2 C8 C10 6.4(2) . . . . ? C3 N2 C8 C10 -172.80(15) . . . . ? C1 N2 C8 C9 -113.91(19) . . . . ? C3 N2 C8 C9 66.9(2) . . . . ? C1 N2 C8 C11 125.50(18) . . . . ? C3 N2 C8 C11 -53.7(2) . . . . ? C18 B C12 C13 -9.4(3) . . . . ? C24 B C12 C13 117.35(19) . . . . ? C18 B C12 C17 166.39(15) . . . . ? C24 B C12 C17 -66.9(2) . . . . ? C17 C12 C13 F1 179.11(15) . . . . ? B C12 C13 F1 -4.8(3) . . . . ? C17 C12 C13 C14 -0.2(3) . . . . ? B C12 C13 C14 175.84(17) . . . . ? F1 C13 C14 F2 0.6(2) . . . . ? C12 C13 C14 F2 179.94(16) . . . . ? F1 C13 C14 C15 -179.48(15) . . . . ? C12 C13 C14 C15 -0.1(3) . . . . ? F2 C14 C15 F3 -0.9(3) . . . . ? C13 C14 C15 F3 179.19(15) . . . . ? F2 C14 C15 C16 179.38(15) . . . . ? C13 C14 C15 C16 -0.6(3) . . . . ? F3 C15 C16 F4 0.0(3) . . . . ? C14 C15 C16 F4 179.75(15) . . . . ? F3 C15 C16 C17 -178.16(15) . . . . ? C14 C15 C16 C17 1.6(3) . . . . ? F4 C16 C17 F5 -1.1(2) . . . . ? C15 C16 C17 F5 177.07(15) . . . . ? F4 C16 C17 C12 179.75(15) . . . . ? C15 C16 C17 C12 -2.1(3) . . . . ? C13 C12 C17 F5 -177.80(14) . . . . ? B C12 C17 F5 5.8(2) . . . . ? C13 C12 C17 C16 1.3(3) . . . . ? B C12 C17 C16 -175.06(16) . . . . ? C12 B C18 C19 -95.15(19) . . . . ? C24 B C18 C19 136.92(17) . . . . ? C12 B C18 C23 84.7(2) . . . . ? C24 B C18 C23 -43.2(2) . . . . ? C23 C18 C19 F6 -178.25(15) . . . . ? B C18 C19 F6 1.6(2) . . . . ? C23 C18 C19 C20 1.3(3) . . . . ? B C18 C19 C20 -178.82(17) . . . . ? F6 C19 C20 F7 -1.4(2) . . . . ? C18 C19 C20 F7 179.02(16) . . . . ? F6 C19 C20 C21 178.20(15) . . . . ? C18 C19 C20 C21 -1.4(3) . . . . ? F7 C20 C21 F8 -0.9(3) . . . . ? C19 C20 C21 F8 179.52(16) . . . . ? F7 C20 C21 C22 -179.62(15) . . . . ? C19 C20 C21 C22 0.7(3) . . . . ? F8 C21 C22 F9 1.3(3) . . . . ? C20 C21 C22 F9 -179.98(15) . . . . ? F8 C21 C22 C23 -179.02(15) . . . . ? C20 C21 C22 C23 -0.3(3) . . . . ? F9 C22 C23 F10 1.4(2) . . . . ? C21 C22 C23 F10 -178.29(15) . . . . ? F9 C22 C23 C18 180.00(15) . . . . ? C21 C22 C23 C18 0.3(3) . . . . ? C19 C18 C23 F10 177.78(14) . . . . ? B C18 C23 F10 -2.1(2) . . . . ? C19 C18 C23 C22 -0.7(2) . . . . ? B C18 C23 C22 179.36(17) . . . . ? C18 B C24 C25 -80.0(2) . . . . ? C12 B C24 C25 151.91(17) . . . . ? C18 B C24 C29 99.2(2) . . . . ? C12 B C24 C29 -29.0(3) . . . . ? C29 C24 C25 F11 -178.22(15) . . . . ? B C24 C25 F11 1.0(3) . . . . ? C29 C24 C25 C26 0.0(3) . . . . ? B C24 C25 C26 179.23(17) . . . . ? F11 C25 C26 F12 -1.1(3) . . . . ? C24 C25 C26 F12 -179.37(17) . . . . ? F11 C25 C26 C27 177.53(17) . . . . ? C24 C25 C26 C27 -0.8(3) . . . . ? F12 C26 C27 F13 0.1(3) . . . . ? C25 C26 C27 F13 -178.59(17) . . . . ? F12 C26 C27 C28 179.26(17) . . . . ? C25 C26 C27 C28 0.6(3) . . . . ? F13 C27 C28 F14 -0.9(3) . . . . ? C26 C27 C28 F14 179.84(16) . . . . ? F13 C27 C28 C29 179.42(16) . . . . ? C26 C27 C28 C29 0.2(3) . . . . ? F14 C28 C29 F15 0.2(2) . . . . ? C27 C28 C29 F15 179.81(16) . . . . ? F14 C28 C29 C24 179.35(16) . . . . ? C27 C28 C29 C24 -1.0(3) . . . . ? C25 C24 C29 F15 -179.98(15) . . . . ? B C24 C29 F15 0.9(3) . . . . ? C25 C24 C29 C28 0.9(3) . . . . ? B C24 C29 C28 -178.29(17) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.252 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.047 #===END data_dhol41 _database_code_depnum_ccdc_archive 'CCDC 726527' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H30 B F15 N2 O' _chemical_formula_weight 766.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.16670(10) _cell_length_b 20.9206(3) _cell_length_c 15.2247(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.3740(10) _cell_angle_gamma 90.00 _cell_volume 3211.41(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 15114 _cell_measurement_theta_min 1.9414 _cell_measurement_theta_max 29.2314 _exptl_crystal_description needle _exptl_crystal_colour clourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1560 _exptl_absorpt_coefficient_mu 0.156 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96601 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.36 (release 29-09-2008 CrysAlis171 .NET) (compiled Sep 29 2008,12:11:20) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur E' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 16.1419 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 67546 _diffrn_reflns_av_R_equivalents 0.0517 _diffrn_reflns_av_sigmaI/netI 0.0712 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 26.37 _reflns_number_total 6570 _reflns_number_gt 3855 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.36 (release 29-09-2008 CrysAlis171 .NET) (compiled Sep 29 2008,12:11:20) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.36 (release 29-09-2008 CrysAlis171 .NET) (compiled Sep 29 2008,12:11:20) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.36 (release 29-09-2008 CrysAlis171 .NET) (compiled Sep 29 2008,12:11:20) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens XP' _computing_publication_material SHELXL-97 _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^)+(0.0467P)^2^] 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 'rigid methyls, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6570 _refine_ls_number_parameters 475 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.0855 _refine_ls_wR_factor_gt 0.0809 _refine_ls_goodness_of_fit_ref 0.846 _refine_ls_restrained_S_all 0.846 _refine_ls_shift/su_max 0.004 _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 B B 0.6136(2) 0.07841(11) 0.27256(14) 0.0211(5) Uani 1 1 d . . . O O 0.56633(12) 0.10924(6) 0.34845(8) 0.0214(3) Uani 1 1 d . . . N1 N 0.63807(15) 0.30760(8) 0.53084(10) 0.0216(4) Uani 1 1 d . . . N2 N 0.63503(15) 0.26044(8) 0.66089(10) 0.0229(4) Uani 1 1 d . . . F1 F 0.32121(10) 0.05816(6) 0.29862(7) 0.0299(3) Uani 1 1 d . . . F2 F 0.14487(11) -0.00783(6) 0.19412(8) 0.0361(3) Uani 1 1 d . . . F3 F 0.21548(11) -0.07475(6) 0.05409(7) 0.0372(3) Uani 1 1 d . . . F4 F 0.47281(11) -0.07304(6) 0.02203(7) 0.0325(3) Uani 1 1 d . . . F5 F 0.65235(10) -0.00323(5) 0.12300(7) 0.0273(3) Uani 1 1 d . . . F6 F 0.85314(11) 0.14451(6) 0.34222(8) 0.0351(3) Uani 1 1 d . . . F7 F 1.08631(11) 0.09614(7) 0.40834(9) 0.0481(4) Uani 1 1 d . . . F8 F 1.12624(12) -0.03277(7) 0.41177(9) 0.0513(4) Uani 1 1 d . . . F9 F 0.92200(13) -0.11157(6) 0.34861(8) 0.0498(4) Uani 1 1 d . . . F10 F 0.68751(11) -0.06515(6) 0.28657(8) 0.0352(3) Uani 1 1 d . . . F11 F 0.83490(10) 0.09830(5) 0.15443(7) 0.0269(3) Uani 1 1 d . . . F12 F 0.84806(10) 0.19250(5) 0.04088(7) 0.0288(3) Uani 1 1 d . . . F13 F 0.65440(11) 0.28310(6) 0.01641(7) 0.0293(3) Uani 1 1 d . . . F14 F 0.44082(10) 0.27365(5) 0.10633(7) 0.0277(3) Uani 1 1 d . . . F15 F 0.42434(10) 0.18027(5) 0.22182(7) 0.0256(3) Uani 1 1 d . . . C1 C 0.63556(16) 0.25246(10) 0.57434(12) 0.0191(4) Uani 1 1 d . . . C2 C 0.6492(2) 0.36045(10) 0.59532(13) 0.0295(5) Uani 1 1 d . . . H2A H 0.5820 0.3938 0.5778 0.035 Uiso 1 1 calc R . . H2B H 0.7386 0.3800 0.6009 0.035 Uiso 1 1 calc R . . C3 C 0.6249(2) 0.32889(10) 0.68060(13) 0.0271(5) Uani 1 1 d . . . H3A H 0.6927 0.3418 0.7300 0.033 Uiso 1 1 calc R . . H3B H 0.5359 0.3397 0.6960 0.033 Uiso 1 1 calc R . . C4 C 0.66819(19) 0.32063(10) 0.43766(13) 0.0266(5) Uani 1 1 d . . . C5 C 0.8140(2) 0.30732(12) 0.43356(15) 0.0426(6) Uani 1 1 d . . . H5A H 0.8679 0.3326 0.4789 0.064 Uiso 1 1 calc R . . H5B H 0.8363 0.3190 0.3749 0.064 Uiso 1 1 calc R . . H5C H 0.8318 0.2618 0.4442 0.064 Uiso 1 1 calc R . . C6 C 0.5804(2) 0.28228(12) 0.36879(14) 0.0408(6) Uani 1 1 d . . . H6A H 0.6038 0.2369 0.3748 0.061 Uiso 1 1 calc R . . H6B H 0.5933 0.2971 0.3094 0.061 Uiso 1 1 calc R . . H6C H 0.4873 0.2880 0.3776 0.061 Uiso 1 1 calc R . . C7 C 0.6386(2) 0.39107(11) 0.41781(16) 0.0453(6) Uani 1 1 d . . . H7A H 0.5448 0.3997 0.4218 0.068 Uiso 1 1 calc R . . H7B H 0.6581 0.4011 0.3580 0.068 Uiso 1 1 calc R . . H7C H 0.6939 0.4176 0.4609 0.068 Uiso 1 1 calc R . . C8 C 0.6337(2) 0.21091(11) 0.73302(13) 0.0296(5) Uani 1 1 d . . . C9 C 0.7600(2) 0.16894(13) 0.73819(15) 0.0480(7) Uani 1 1 d . . . H9A H 0.7702 0.1446 0.7936 0.072 Uiso 1 1 calc R . . H9B H 0.8378 0.1964 0.7363 0.072 Uiso 1 1 calc R . . H9C H 0.7521 0.1394 0.6879 0.072 Uiso 1 1 calc R . . C10 C 0.5097(2) 0.17075(13) 0.71979(15) 0.0475(7) Uani 1 1 d . . . H10A H 0.4317 0.1987 0.7143 0.071 Uiso 1 1 calc R . . H10B H 0.5080 0.1422 0.7707 0.071 Uiso 1 1 calc R . . H10C H 0.5089 0.1452 0.6657 0.071 Uiso 1 1 calc R . . C11 C 0.6420(2) 0.24508(12) 0.82176(14) 0.0471(7) Uani 1 1 d . . . H11A H 0.5656 0.2736 0.8218 0.071 Uiso 1 1 calc R . . H11B H 0.7240 0.2702 0.8314 0.071 Uiso 1 1 calc R . . H11C H 0.6418 0.2135 0.8693 0.071 Uiso 1 1 calc R . . C12 C 0.62538(18) 0.18807(10) 0.53093(13) 0.0234(5) Uani 1 1 d . . . H12A H 0.6637 0.1555 0.5740 0.028 Uiso 1 1 calc R . . H12B H 0.6780 0.1881 0.4806 0.028 Uiso 1 1 calc R . . C13 C 0.48185(19) 0.16998(10) 0.49730(13) 0.0255(5) Uani 1 1 d . . . H13A H 0.4237 0.1842 0.5409 0.031 Uiso 1 1 calc R . . H13B H 0.4538 0.1927 0.4410 0.031 Uiso 1 1 calc R . . C14 C 0.4644(2) 0.09846(10) 0.48236(13) 0.0297(5) Uani 1 1 d . . . H14A H 0.3727 0.0900 0.4544 0.036 Uiso 1 1 calc R . . H14B H 0.4768 0.0765 0.5404 0.036 Uiso 1 1 calc R . . C15 C 0.5611(2) 0.07069(10) 0.42416(13) 0.0286(5) Uani 1 1 d . . . H15A H 0.6506 0.0680 0.4584 0.034 Uiso 1 1 calc R . . H15B H 0.5329 0.0269 0.4056 0.034 Uiso 1 1 calc R . . C21 C 0.50007(18) 0.03024(9) 0.21826(12) 0.0193(4) Uani 1 1 d . . . C22 C 0.36722(19) 0.02667(9) 0.23119(12) 0.0219(5) Uani 1 1 d . . . C23 C 0.27275(19) -0.00751(10) 0.17768(13) 0.0245(5) Uani 1 1 d . . . C24 C 0.3070(2) -0.04063(10) 0.10681(13) 0.0246(5) Uani 1 1 d . . . C25 C 0.4365(2) -0.03969(10) 0.09071(12) 0.0237(5) Uani 1 1 d . . . C26 C 0.52741(18) -0.00418(9) 0.14489(12) 0.0204(4) Uani 1 1 d . . . C31 C 0.75720(19) 0.04255(10) 0.30766(12) 0.0220(5) Uani 1 1 d . . . C32 C 0.8647(2) 0.07987(11) 0.34228(13) 0.0280(5) Uani 1 1 d . . . C33 C 0.9873(2) 0.05650(11) 0.37702(14) 0.0314(5) Uani 1 1 d . . . C34 C 1.0073(2) -0.00806(12) 0.37917(14) 0.0358(6) Uani 1 1 d . . . C35 C 0.9054(2) -0.04775(11) 0.34772(14) 0.0322(5) Uani 1 1 d . . . C36 C 0.7838(2) -0.02184(10) 0.31421(13) 0.0264(5) Uani 1 1 d . . . C41 C 0.63156(18) 0.13513(9) 0.19918(12) 0.0183(4) Uani 1 1 d . . . C42 C 0.53474(17) 0.18158(9) 0.18052(12) 0.0181(4) Uani 1 1 d . . . C43 C 0.54045(17) 0.23067(9) 0.12078(12) 0.0191(4) Uani 1 1 d . . . C44 C 0.64674(18) 0.23529(9) 0.07419(12) 0.0205(5) Uani 1 1 d . . . C45 C 0.74348(18) 0.18976(10) 0.08731(12) 0.0207(5) Uani 1 1 d . . . C46 C 0.73394(18) 0.14122(9) 0.14767(12) 0.0200(4) 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 B 0.0218(12) 0.0174(14) 0.0246(13) -0.0014(10) 0.0043(10) 0.0000(10) O 0.0291(7) 0.0164(8) 0.0195(7) 0.0011(6) 0.0058(6) 0.0002(6) N1 0.0208(9) 0.0206(10) 0.0235(9) 0.0008(7) 0.0028(7) -0.0023(7) N2 0.0241(9) 0.0245(11) 0.0204(9) -0.0006(7) 0.0039(7) -0.0029(8) F1 0.0281(6) 0.0309(8) 0.0328(7) -0.0076(5) 0.0121(5) -0.0019(5) F2 0.0252(7) 0.0410(8) 0.0430(7) -0.0040(6) 0.0078(5) -0.0087(6) F3 0.0401(7) 0.0361(8) 0.0340(7) -0.0061(6) -0.0006(6) -0.0158(6) F4 0.0450(7) 0.0267(7) 0.0263(7) -0.0085(5) 0.0064(5) 0.0004(6) F5 0.0262(6) 0.0264(7) 0.0308(7) -0.0044(5) 0.0095(5) 0.0021(5) F6 0.0304(7) 0.0232(8) 0.0489(8) -0.0047(6) -0.0056(6) -0.0009(6) F7 0.0283(7) 0.0543(10) 0.0568(9) -0.0071(7) -0.0125(6) -0.0014(7) F8 0.0375(8) 0.0591(11) 0.0537(9) 0.0057(7) -0.0079(7) 0.0221(7) F9 0.0602(9) 0.0284(9) 0.0589(9) 0.0072(7) 0.0001(7) 0.0203(7) F10 0.0420(7) 0.0183(7) 0.0436(7) 0.0040(6) -0.0006(6) 0.0015(6) F11 0.0221(6) 0.0233(7) 0.0370(7) 0.0005(5) 0.0101(5) 0.0042(5) F12 0.0268(6) 0.0296(7) 0.0329(7) -0.0003(5) 0.0148(5) -0.0035(5) F13 0.0381(7) 0.0246(7) 0.0265(6) 0.0063(5) 0.0090(5) -0.0020(5) F14 0.0272(6) 0.0219(7) 0.0341(7) 0.0055(5) 0.0050(5) 0.0058(5) F15 0.0221(6) 0.0245(7) 0.0319(6) 0.0035(5) 0.0107(5) 0.0033(5) C1 0.0107(10) 0.0258(13) 0.0207(11) 0.0013(9) 0.0017(8) -0.0007(9) C2 0.0315(12) 0.0225(13) 0.0341(13) -0.0038(10) 0.0019(10) -0.0020(10) C3 0.0234(11) 0.0273(13) 0.0306(12) -0.0064(10) 0.0030(9) 0.0017(10) C4 0.0285(12) 0.0288(13) 0.0231(11) 0.0084(10) 0.0059(9) -0.0063(10) C5 0.0398(14) 0.0534(18) 0.0374(14) 0.0093(12) 0.0160(11) -0.0053(12) C6 0.0506(15) 0.0449(16) 0.0258(12) 0.0103(11) 0.0010(11) -0.0093(12) C7 0.0570(16) 0.0349(16) 0.0431(14) 0.0138(12) 0.0032(12) -0.0061(12) C8 0.0332(12) 0.0380(15) 0.0187(11) 0.0033(10) 0.0079(9) -0.0114(11) C9 0.0556(16) 0.0517(18) 0.0368(14) 0.0185(12) 0.0062(12) 0.0027(13) C10 0.0509(16) 0.065(2) 0.0273(13) 0.0102(12) 0.0074(11) -0.0243(14) C11 0.0711(17) 0.0480(17) 0.0229(12) -0.0019(11) 0.0085(12) -0.0100(14) C12 0.0258(11) 0.0219(12) 0.0234(11) 0.0012(9) 0.0065(9) -0.0010(9) C13 0.0287(12) 0.0258(13) 0.0226(11) -0.0005(9) 0.0056(9) -0.0025(10) C14 0.0419(13) 0.0237(13) 0.0240(11) 0.0011(9) 0.0066(10) -0.0078(10) C15 0.0426(13) 0.0153(12) 0.0285(12) 0.0016(9) 0.0065(10) -0.0005(10) C21 0.0237(11) 0.0113(11) 0.0233(11) 0.0037(8) 0.0042(9) 0.0016(8) C22 0.0297(12) 0.0158(12) 0.0209(11) -0.0006(9) 0.0058(9) 0.0021(9) C23 0.0197(11) 0.0234(13) 0.0306(12) 0.0056(10) 0.0048(9) -0.0039(9) C24 0.0322(13) 0.0164(12) 0.0236(11) 0.0003(9) -0.0021(10) -0.0078(10) C25 0.0362(13) 0.0167(12) 0.0189(11) -0.0008(9) 0.0057(10) 0.0009(10) C26 0.0216(11) 0.0151(11) 0.0249(11) 0.0021(9) 0.0046(9) 0.0009(9) C31 0.0268(11) 0.0192(12) 0.0202(11) -0.0002(9) 0.0041(9) 0.0013(9) C32 0.0310(12) 0.0244(14) 0.0280(12) 0.0001(10) 0.0016(10) 0.0050(10) C33 0.0268(12) 0.0356(15) 0.0306(12) -0.0023(10) -0.0001(10) 0.0025(11) C34 0.0288(13) 0.0469(17) 0.0302(13) 0.0026(11) -0.0019(10) 0.0122(12) C35 0.0428(14) 0.0225(14) 0.0316(13) 0.0066(10) 0.0064(11) 0.0158(11) C36 0.0308(12) 0.0233(13) 0.0249(11) -0.0015(9) 0.0024(10) -0.0037(10) C41 0.0190(10) 0.0163(11) 0.0190(10) -0.0043(8) 0.0004(8) -0.0032(9) C42 0.0142(10) 0.0193(12) 0.0214(10) -0.0027(9) 0.0045(8) -0.0023(9) C43 0.0167(10) 0.0152(11) 0.0243(11) -0.0036(8) -0.0017(9) 0.0032(8) C44 0.0276(11) 0.0162(12) 0.0170(10) -0.0004(8) 0.0006(9) -0.0059(9) C45 0.0190(10) 0.0227(12) 0.0213(11) -0.0050(9) 0.0062(8) -0.0043(9) C46 0.0176(10) 0.0177(12) 0.0244(11) -0.0060(9) 0.0019(9) 0.0006(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 B O 1.457(2) . ? B C41 1.656(3) . ? B C31 1.667(3) . ? B C21 1.669(3) . ? O C15 1.413(2) . ? N1 C1 1.332(2) . ? N1 C2 1.473(3) . ? N1 C4 1.514(2) . ? N2 C1 1.329(2) . ? N2 C3 1.470(3) . ? N2 C8 1.511(3) . ? F1 C22 1.353(2) . ? F2 C23 1.355(2) . ? F3 C24 1.352(2) . ? F4 C25 1.347(2) . ? F5 C26 1.354(2) . ? F6 C32 1.357(2) . ? F7 C33 1.344(2) . ? F8 C34 1.349(2) . ? F9 C35 1.346(2) . ? F10 C36 1.361(2) . ? F11 C46 1.358(2) . ? F12 C45 1.351(2) . ? F13 C44 1.341(2) . ? F14 C43 1.351(2) . ? F15 C42 1.355(2) . ? C1 C12 1.498(3) . ? C2 C3 1.505(3) . ? C4 C6 1.516(3) . ? C4 C5 1.517(3) . ? C4 C7 1.527(3) . ? C8 C10 1.506(3) . ? C8 C11 1.521(3) . ? C8 C9 1.549(3) . ? C12 C13 1.531(3) . ? C13 C14 1.520(3) . ? C14 C15 1.521(3) . ? C21 C26 1.387(3) . ? C21 C22 1.392(3) . ? C22 C23 1.377(3) . ? C23 C24 1.365(3) . ? C24 C25 1.369(3) . ? C25 C26 1.375(3) . ? C31 C36 1.375(3) . ? C31 C32 1.391(3) . ? C32 C33 1.380(3) . ? C33 C34 1.366(3) . ? C34 C35 1.366(3) . ? C35 C36 1.385(3) . ? C41 C42 1.386(3) . ? C41 C46 1.387(3) . ? C42 C43 1.378(3) . ? C43 C44 1.370(3) . ? C44 C45 1.365(3) . ? C45 C46 1.381(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O B C41 107.09(17) . . ? O B C31 108.01(15) . . ? C41 B C31 111.75(16) . . ? O B C21 112.50(16) . . ? C41 B C21 103.16(14) . . ? C31 B C21 114.11(17) . . ? C15 O B 116.40(15) . . ? C1 N1 C2 108.87(16) . . ? C1 N1 C4 129.86(17) . . ? C2 N1 C4 118.80(16) . . ? C1 N2 C3 109.52(16) . . ? C1 N2 C8 129.49(17) . . ? C3 N2 C8 120.82(16) . . ? N2 C1 N1 112.77(18) . . ? N2 C1 C12 122.79(18) . . ? N1 C1 C12 124.33(17) . . ? N1 C2 C3 103.80(17) . . ? N2 C3 C2 103.17(16) . . ? N1 C4 C6 112.38(16) . . ? N1 C4 C5 108.76(16) . . ? C6 C4 C5 111.46(19) . . ? N1 C4 C7 107.51(17) . . ? C6 C4 C7 106.87(17) . . ? C5 C4 C7 109.74(18) . . ? C10 C8 N2 111.75(16) . . ? C10 C8 C11 109.33(18) . . ? N2 C8 C11 108.58(18) . . ? C10 C8 C9 111.4(2) . . ? N2 C8 C9 109.92(16) . . ? C11 C8 C9 105.66(18) . . ? C1 C12 C13 112.26(16) . . ? C14 C13 C12 112.41(17) . . ? C13 C14 C15 113.05(17) . . ? O C15 C14 110.60(16) . . ? C26 C21 C22 112.61(17) . . ? C26 C21 B 121.01(17) . . ? C22 C21 B 125.75(17) . . ? F1 C22 C23 114.77(17) . . ? F1 C22 C21 121.17(17) . . ? C23 C22 C21 124.06(18) . . ? F2 C23 C24 119.47(17) . . ? F2 C23 C22 120.41(18) . . ? C24 C23 C22 120.12(18) . . ? F3 C24 C23 120.74(18) . . ? F3 C24 C25 120.36(18) . . ? C23 C24 C25 118.90(18) . . ? F4 C25 C24 119.80(18) . . ? F4 C25 C26 121.00(18) . . ? C24 C25 C26 119.20(18) . . ? F5 C26 C25 116.11(17) . . ? F5 C26 C21 118.81(16) . . ? C25 C26 C21 125.09(18) . . ? C36 C31 C32 112.62(18) . . ? C36 C31 B 128.33(18) . . ? C32 C31 B 118.83(18) . . ? F6 C32 C33 115.29(18) . . ? F6 C32 C31 119.69(17) . . ? C33 C32 C31 125.0(2) . . ? F7 C33 C34 119.94(19) . . ? F7 C33 C32 121.1(2) . . ? C34 C33 C32 119.0(2) . . ? F8 C34 C33 120.8(2) . . ? F8 C34 C35 120.0(2) . . ? C33 C34 C35 119.2(2) . . ? F9 C35 C34 120.71(19) . . ? F9 C35 C36 119.8(2) . . ? C34 C35 C36 119.5(2) . . ? F10 C36 C31 120.19(17) . . ? F10 C36 C35 115.20(19) . . ? C31 C36 C35 124.6(2) . . ? C42 C41 C46 112.60(17) . . ? C42 C41 B 120.24(17) . . ? C46 C41 B 127.09(17) . . ? F15 C42 C43 115.40(16) . . ? F15 C42 C41 119.94(17) . . ? C43 C42 C41 124.66(17) . . ? F14 C43 C44 119.57(17) . . ? F14 C43 C42 120.61(17) . . ? C44 C43 C42 119.81(17) . . ? F13 C44 C45 121.00(17) . . ? F13 C44 C43 120.55(17) . . ? C45 C44 C43 118.45(18) . . ? F12 C45 C44 119.61(17) . . ? F12 C45 C46 120.42(17) . . ? C44 C45 C46 119.96(18) . . ? F11 C46 C45 114.81(16) . . ? F11 C46 C41 120.75(17) . . ? C45 C46 C41 124.44(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C41 B O C15 -171.80(15) . . . . ? C31 B O C15 -51.3(2) . . . . ? C21 B O C15 75.5(2) . . . . ? C3 N2 C1 N1 5.2(2) . . . . ? C8 N2 C1 N1 -179.38(17) . . . . ? C3 N2 C1 C12 -171.04(16) . . . . ? C8 N2 C1 C12 4.4(3) . . . . ? C2 N1 C1 N2 4.0(2) . . . . ? C4 N1 C1 N2 165.58(16) . . . . ? C2 N1 C1 C12 -179.76(16) . . . . ? C4 N1 C1 C12 -18.2(3) . . . . ? C1 N1 C2 C3 -11.1(2) . . . . ? C4 N1 C2 C3 -175.01(15) . . . . ? C1 N2 C3 C2 -11.8(2) . . . . ? C8 N2 C3 C2 172.38(16) . . . . ? N1 C2 C3 N2 13.25(19) . . . . ? C1 N1 C4 C6 55.2(3) . . . . ? C2 N1 C4 C6 -144.84(18) . . . . ? C1 N1 C4 C5 -68.7(2) . . . . ? C2 N1 C4 C5 91.3(2) . . . . ? C1 N1 C4 C7 172.48(18) . . . . ? C2 N1 C4 C7 -27.5(2) . . . . ? C1 N2 C8 C10 -62.7(3) . . . . ? C3 N2 C8 C10 112.2(2) . . . . ? C1 N2 C8 C11 176.61(18) . . . . ? C3 N2 C8 C11 -8.4(2) . . . . ? C1 N2 C8 C9 61.5(2) . . . . ? C3 N2 C8 C9 -123.57(19) . . . . ? N2 C1 C12 C13 92.4(2) . . . . ? N1 C1 C12 C13 -83.4(2) . . . . ? C1 C12 C13 C14 -160.51(17) . . . . ? C12 C13 C14 C15 -52.3(2) . . . . ? B O C15 C14 -158.11(16) . . . . ? C13 C14 C15 O -46.5(2) . . . . ? O B C21 C26 -178.95(17) . . . . ? C41 B C21 C26 66.0(2) . . . . ? C31 B C21 C26 -55.4(2) . . . . ? O B C21 C22 10.8(3) . . . . ? C41 B C21 C22 -104.2(2) . . . . ? C31 B C21 C22 134.34(19) . . . . ? C26 C21 C22 F1 -178.80(17) . . . . ? B C21 C22 F1 -7.9(3) . . . . ? C26 C21 C22 C23 0.4(3) . . . . ? B C21 C22 C23 171.31(19) . . . . ? F1 C22 C23 F2 0.1(3) . . . . ? C21 C22 C23 F2 -179.09(18) . . . . ? F1 C22 C23 C24 179.21(18) . . . . ? C21 C22 C23 C24 0.0(3) . . . . ? F2 C23 C24 F3 -1.4(3) . . . . ? C22 C23 C24 F3 179.53(17) . . . . ? F2 C23 C24 C25 179.72(18) . . . . ? C22 C23 C24 C25 0.6(3) . . . . ? F3 C24 C25 F4 -0.1(3) . . . . ? C23 C24 C25 F4 178.77(17) . . . . ? F3 C24 C25 C26 179.47(17) . . . . ? C23 C24 C25 C26 -1.6(3) . . . . ? F4 C25 C26 F5 2.3(3) . . . . ? C24 C25 C26 F5 -177.33(17) . . . . ? F4 C25 C26 C21 -178.24(18) . . . . ? C24 C25 C26 C21 2.2(3) . . . . ? C22 C21 C26 F5 178.01(16) . . . . ? B C21 C26 F5 6.6(3) . . . . ? C22 C21 C26 C25 -1.5(3) . . . . ? B C21 C26 C25 -172.89(18) . . . . ? O B C31 C36 110.9(2) . . . . ? C41 B C31 C36 -131.6(2) . . . . ? C21 B C31 C36 -15.0(3) . . . . ? O B C31 C32 -63.2(2) . . . . ? C41 B C31 C32 54.3(2) . . . . ? C21 B C31 C32 170.87(17) . . . . ? C36 C31 C32 F6 -178.75(18) . . . . ? B C31 C32 F6 -3.7(3) . . . . ? C36 C31 C32 C33 2.2(3) . . . . ? B C31 C32 C33 177.16(19) . . . . ? F6 C32 C33 F7 0.2(3) . . . . ? C31 C32 C33 F7 179.31(19) . . . . ? F6 C32 C33 C34 -179.72(19) . . . . ? C31 C32 C33 C34 -0.6(3) . . . . ? F7 C33 C34 F8 -0.6(3) . . . . ? C32 C33 C34 F8 179.30(18) . . . . ? F7 C33 C34 C35 179.48(19) . . . . ? C32 C33 C34 C35 -0.6(3) . . . . ? F8 C34 C35 F9 -0.2(3) . . . . ? C33 C34 C35 F9 179.8(2) . . . . ? F8 C34 C35 C36 -179.84(18) . . . . ? C33 C34 C35 C36 0.1(3) . . . . ? C32 C31 C36 F10 177.44(17) . . . . ? B C31 C36 F10 3.0(3) . . . . ? C32 C31 C36 C35 -2.7(3) . . . . ? B C31 C36 C35 -177.16(19) . . . . ? F9 C35 C36 F10 1.9(3) . . . . ? C34 C35 C36 F10 -178.40(18) . . . . ? F9 C35 C36 C31 -177.91(19) . . . . ? C34 C35 C36 C31 1.8(3) . . . . ? O B C41 C42 -44.1(2) . . . . ? C31 B C41 C42 -162.18(16) . . . . ? C21 B C41 C42 74.8(2) . . . . ? O B C41 C46 139.28(18) . . . . ? C31 B C41 C46 21.2(3) . . . . ? C21 B C41 C46 -101.8(2) . . . . ? C46 C41 C42 F15 176.48(16) . . . . ? B C41 C42 F15 -0.6(3) . . . . ? C46 C41 C42 C43 -3.0(3) . . . . ? B C41 C42 C43 179.94(18) . . . . ? F15 C42 C43 F14 0.1(3) . . . . ? C41 C42 C43 F14 179.54(16) . . . . ? F15 C42 C43 C44 -178.56(16) . . . . ? C41 C42 C43 C44 0.9(3) . . . . ? F14 C43 C44 F13 2.0(3) . . . . ? C42 C43 C44 F13 -179.39(16) . . . . ? F14 C43 C44 C45 -177.32(16) . . . . ? C42 C43 C44 C45 1.3(3) . . . . ? F13 C44 C45 F12 -0.6(3) . . . . ? C43 C44 C45 F12 178.69(16) . . . . ? F13 C44 C45 C46 179.52(16) . . . . ? C43 C44 C45 C46 -1.2(3) . . . . ? F12 C45 C46 F11 -0.7(3) . . . . ? C44 C45 C46 F11 179.26(15) . . . . ? F12 C45 C46 C41 178.94(16) . . . . ? C44 C45 C46 C41 -1.2(3) . . . . ? C42 C41 C46 F11 -177.35(16) . . . . ? B C41 C46 F11 -0.5(3) . . . . ? C42 C41 C46 C45 3.1(3) . . . . ? B C41 C46 C45 179.94(18) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.497 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.045 #===END data_dhol45 _database_code_depnum_ccdc_archive 'CCDC 726528' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32.50 H22.50 B F15 N2' _chemical_formula_weight 736.83 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.6118(16) _cell_length_b 15.5335(8) _cell_length_c 19.8810(12) _cell_angle_alpha 90.00 _cell_angle_beta 115.316(8) _cell_angle_gamma 90.00 _cell_volume 6591.5(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 19852 _cell_measurement_theta_min 3.5138 _cell_measurement_theta_max 75.7013 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2972 _exptl_absorpt_coefficient_mu 1.310 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.68735 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.36 (release 29-09-2008 CrysAlis171 .NET) (compiled Sep 29 2008,12:11:20) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Oxford Diffraction Nova A' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 10.3543 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 40766 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 76.08 _reflns_number_total 6805 _reflns_number_gt 5806 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.36 (release 29-09-2008 CrysAlis171 .NET) (compiled Sep 29 2008,12:11:20) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.36 (release 29-09-2008 CrysAlis171 .NET) (compiled Sep 29 2008,12:11:20) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.36 (release 29-09-2008 CrysAlis171 .NET) (compiled Sep 29 2008,12:11:20) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _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. The toluene molecule is disordered over an inversion centre. The toluene ring was refined as an idealised hexagon. Nonetheless, residual electron density in the toluene region may indicate that the disorder model is not perfect. ; _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^)+(0.1253P)^2^+3.4259P] 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 'rigid methyls, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6805 _refine_ls_number_parameters 482 _refine_ls_number_restraints 61 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1715 _refine_ls_wR_factor_gt 0.1613 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.104 _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 B B 0.18307(10) 0.57713(14) 0.27890(11) 0.0264(4) Uani 1 1 d . . . F1 F 0.22215(6) 0.57634(9) 0.43831(6) 0.0362(3) Uani 1 1 d . . . F2 F 0.31787(7) 0.66049(11) 0.54232(7) 0.0494(4) Uani 1 1 d . . . F3 F 0.39910(7) 0.75174(10) 0.50456(7) 0.0494(4) Uani 1 1 d . . . F4 F 0.37992(6) 0.75941(9) 0.36084(7) 0.0381(3) Uani 1 1 d . . . F5 F 0.28057(5) 0.68653(8) 0.25478(6) 0.0307(3) Uani 1 1 d . . . F6 F 0.27649(6) 0.44651(9) 0.39087(7) 0.0386(3) Uani 1 1 d . . . F7 F 0.25162(7) 0.28339(9) 0.40417(8) 0.0468(3) Uani 1 1 d . . . F8 F 0.13716(7) 0.21513(8) 0.31750(8) 0.0445(3) Uani 1 1 d . . . F9 F 0.04754(6) 0.31599(8) 0.21502(7) 0.0390(3) Uani 1 1 d . . . F10 F 0.07116(5) 0.47992(8) 0.19851(6) 0.0331(3) Uani 1 1 d . . . F11 F 0.16379(5) 0.76226(7) 0.25319(6) 0.0315(3) Uani 1 1 d . . . F12 F 0.09125(6) 0.86607(8) 0.28712(7) 0.0368(3) Uani 1 1 d . . . F13 F 0.01764(6) 0.80328(9) 0.35047(7) 0.0385(3) Uani 1 1 d . . . F14 F 0.01933(6) 0.63111(9) 0.37801(7) 0.0374(3) Uani 1 1 d . . . F15 F 0.08992(6) 0.52590(8) 0.34539(6) 0.0340(3) Uani 1 1 d . . . N1 N 0.12385(7) 0.63487(11) 0.07268(8) 0.0270(3) Uani 1 1 d . . . N2 N 0.20355(7) 0.56044(10) 0.14987(8) 0.0266(3) Uani 1 1 d . . . C1 C 0.17363(9) 0.58962(13) 0.08036(10) 0.0291(4) Uani 1 1 d . . . H1 H 0.1864 0.5793 0.0417 0.035 Uiso 1 1 calc R . . C2 C 0.17099(8) 0.58919(12) 0.19137(10) 0.0254(4) Uani 1 1 d . . . C3 C 0.12154(8) 0.63443(12) 0.14077(10) 0.0268(4) Uani 1 1 d . . . H3 H 0.0901 0.6617 0.1510 0.032 Uiso 1 1 calc R . . C4 C 0.25525(9) 0.49456(13) 0.16663(10) 0.0304(4) Uani 1 1 d . . . C5 C 0.30292(10) 0.49775(15) 0.24726(11) 0.0351(4) Uani 1 1 d . . . H5A H 0.3277 0.5506 0.2561 0.053 Uiso 1 1 calc R . . H5B H 0.3307 0.4477 0.2582 0.053 Uiso 1 1 calc R . . H5C H 0.2812 0.4969 0.2796 0.053 Uiso 1 1 calc R . . C6 C 0.22333(11) 0.40660(14) 0.14768(13) 0.0402(5) Uani 1 1 d . . . H6A H 0.2048 0.3936 0.1822 0.060 Uiso 1 1 calc R . . H6B H 0.2543 0.3624 0.1521 0.060 Uiso 1 1 calc R . . H6C H 0.1904 0.4074 0.0966 0.060 Uiso 1 1 calc R . . C7 C 0.28921(10) 0.51353(15) 0.11771(11) 0.0365(4) Uani 1 1 d . . . H7A H 0.2612 0.5012 0.0656 0.055 Uiso 1 1 calc R . . H7B H 0.3266 0.4772 0.1334 0.055 Uiso 1 1 calc R . . H7C H 0.3015 0.5743 0.1228 0.055 Uiso 1 1 calc R . . C8 C 0.07625(9) 0.67511(14) 0.00249(10) 0.0314(4) Uani 1 1 d . . . C9 C 0.01844(10) 0.61780(18) -0.02672(12) 0.0428(5) Uani 1 1 d . . . H9A H 0.0291 0.5615 -0.0404 0.064 Uiso 1 1 calc R . . H9B H -0.0146 0.6446 -0.0706 0.064 Uiso 1 1 calc R . . H9C H 0.0036 0.6103 0.0120 0.064 Uiso 1 1 calc R . . C10 C 0.10389(11) 0.68090(16) -0.05396(11) 0.0392(5) Uani 1 1 d . . . H10A H 0.1434 0.7130 -0.0323 0.059 Uiso 1 1 calc R . . H10B H 0.0743 0.7106 -0.0987 0.059 Uiso 1 1 calc R . . H10C H 0.1118 0.6228 -0.0672 0.059 Uiso 1 1 calc R . . C11 C 0.06179(13) 0.76481(16) 0.02204(13) 0.0454(5) Uani 1 1 d . . . H11A H 0.0429 0.7601 0.0572 0.068 Uiso 1 1 calc R . . H11B H 0.0325 0.7939 -0.0233 0.068 Uiso 1 1 calc R . . H11C H 0.1007 0.7982 0.0448 0.068 Uiso 1 1 calc R . . C21 C 0.24771(9) 0.62216(12) 0.34095(10) 0.0274(4) Uani 1 1 d . . . C22 C 0.26037(9) 0.62084(14) 0.41620(10) 0.0310(4) Uani 1 1 d . . . C23 C 0.30953(11) 0.66346(15) 0.47128(11) 0.0363(5) Uani 1 1 d . . . C24 C 0.35051(10) 0.70998(15) 0.45262(11) 0.0361(4) Uani 1 1 d . . . C25 C 0.34035(9) 0.71402(14) 0.37932(11) 0.0318(4) Uani 1 1 d . . . C26 C 0.28904(9) 0.67300(13) 0.32556(10) 0.0282(4) Uani 1 1 d . . . C31 C 0.17509(9) 0.47362(12) 0.29307(10) 0.0286(4) Uani 1 1 d . . . C32 C 0.21851(10) 0.41856(14) 0.34473(10) 0.0318(4) Uani 1 1 d . . . C33 C 0.20699(11) 0.33290(14) 0.35286(11) 0.0357(4) Uani 1 1 d . . . C34 C 0.14950(11) 0.29756(13) 0.30949(12) 0.0353(4) Uani 1 1 d . . . C35 C 0.10421(10) 0.34902(14) 0.25716(11) 0.0323(4) Uani 1 1 d . . . C36 C 0.11821(9) 0.43369(13) 0.24985(10) 0.0294(4) Uani 1 1 d . . . C41 C 0.12966(8) 0.63609(12) 0.29296(9) 0.0267(4) Uani 1 1 d . . . C42 C 0.12725(9) 0.72486(13) 0.28196(10) 0.0283(4) Uani 1 1 d . . . C43 C 0.09044(9) 0.78150(13) 0.29987(10) 0.0306(4) Uani 1 1 d . . . C44 C 0.05332(9) 0.75009(14) 0.33205(10) 0.0316(4) Uani 1 1 d . . . C45 C 0.05411(9) 0.66308(14) 0.34534(10) 0.0306(4) Uani 1 1 d . . . C46 C 0.09154(9) 0.60876(13) 0.32618(10) 0.0286(4) Uani 1 1 d . . . C91 C 0.0792(4) 0.9913(6) -0.0635(5) 0.099(3) Uani 0.50 1 d PGDU A -1 H91 H 0.1073 0.9885 -0.0862 0.119 Uiso 0.50 1 calc PR A -1 C92 C 0.1023(2) 0.9985(5) 0.0134(5) 0.236(7) Uani 0.50 1 d PGDU A -1 H92 H 0.1462 1.0006 0.0432 0.283 Uiso 0.50 1 calc PR A -1 C93 C 0.0612(3) 1.0026(4) 0.0466(3) 0.084(2) Uani 0.50 1 d PGDU A -1 H93 H 0.0770 1.0075 0.0991 0.100 Uiso 0.50 1 calc PR A -1 C94 C -0.0031(3) 0.9995(5) 0.0029(4) 0.237(6) Uani 0.50 1 d PGDU A -1 C95 C -0.0262(2) 0.9922(5) -0.0739(4) 0.088(2) Uani 0.50 1 d PGDU A -1 H95 H -0.0702 0.9901 -0.1038 0.106 Uiso 0.50 1 calc PR A -1 C96 C 0.0149(4) 0.9881(5) -0.1071(3) 0.197(6) Uani 0.50 1 d PGDU A -1 H96 H -0.0009 0.9832 -0.1597 0.236 Uiso 0.50 1 calc PR A -1 C97 C -0.0449(4) 0.9987(5) 0.0299(5) 0.086(2) Uani 0.50 1 d PDU A -1 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 B 0.0291(9) 0.0330(10) 0.0174(8) 0.0001(7) 0.0102(7) -0.0018(8) F1 0.0390(6) 0.0499(7) 0.0199(5) 0.0021(5) 0.0129(5) -0.0104(5) F2 0.0577(8) 0.0692(9) 0.0174(6) -0.0032(5) 0.0124(5) -0.0242(7) F3 0.0498(7) 0.0667(9) 0.0224(6) -0.0056(6) 0.0065(5) -0.0262(7) F4 0.0355(6) 0.0497(7) 0.0279(6) 0.0021(5) 0.0125(5) -0.0118(5) F5 0.0329(6) 0.0414(6) 0.0187(5) 0.0010(4) 0.0119(4) -0.0044(5) F6 0.0357(6) 0.0448(7) 0.0283(6) 0.0069(5) 0.0070(5) 0.0033(5) F7 0.0536(8) 0.0443(7) 0.0411(7) 0.0162(6) 0.0190(6) 0.0136(6) F8 0.0658(9) 0.0320(6) 0.0486(8) 0.0046(5) 0.0368(7) -0.0004(6) F9 0.0446(7) 0.0402(7) 0.0364(6) -0.0069(5) 0.0214(6) -0.0116(5) F10 0.0329(6) 0.0381(6) 0.0243(5) 0.0007(4) 0.0083(5) -0.0027(5) F11 0.0353(6) 0.0336(6) 0.0279(5) -0.0006(4) 0.0158(5) -0.0041(4) F12 0.0409(6) 0.0322(6) 0.0348(6) -0.0038(5) 0.0139(5) 0.0002(5) F13 0.0355(6) 0.0491(7) 0.0305(6) -0.0081(5) 0.0136(5) 0.0066(5) F14 0.0351(6) 0.0532(7) 0.0306(6) -0.0033(5) 0.0205(5) -0.0042(5) F15 0.0419(6) 0.0359(6) 0.0306(6) 0.0015(5) 0.0217(5) -0.0033(5) N1 0.0292(7) 0.0347(8) 0.0174(7) 0.0015(6) 0.0103(6) 0.0015(6) N2 0.0293(7) 0.0308(8) 0.0197(7) -0.0009(6) 0.0105(6) 0.0024(6) C1 0.0331(9) 0.0357(10) 0.0207(8) -0.0003(7) 0.0135(7) 0.0025(7) C2 0.0269(8) 0.0303(9) 0.0196(8) -0.0010(6) 0.0105(7) -0.0012(7) C3 0.0273(8) 0.0354(9) 0.0189(8) -0.0009(7) 0.0111(7) -0.0004(7) C4 0.0326(9) 0.0343(10) 0.0246(9) -0.0007(7) 0.0125(8) 0.0061(8) C5 0.0324(9) 0.0458(11) 0.0257(9) 0.0015(8) 0.0111(8) 0.0094(8) C6 0.0425(11) 0.0334(11) 0.0402(11) -0.0016(8) 0.0133(9) 0.0042(8) C7 0.0396(10) 0.0446(11) 0.0298(10) 0.0003(8) 0.0191(9) 0.0095(9) C8 0.0330(9) 0.0425(11) 0.0182(8) 0.0060(7) 0.0105(7) 0.0063(8) C9 0.0347(10) 0.0659(15) 0.0237(9) 0.0044(9) 0.0086(8) -0.0019(10) C10 0.0413(11) 0.0565(13) 0.0236(9) 0.0090(9) 0.0175(8) 0.0062(9) C11 0.0593(14) 0.0459(12) 0.0319(11) 0.0105(9) 0.0204(10) 0.0186(11) C21 0.0288(8) 0.0340(9) 0.0184(8) 0.0007(7) 0.0092(7) 0.0006(7) C22 0.0323(9) 0.0390(10) 0.0210(9) 0.0021(7) 0.0108(7) -0.0051(8) C23 0.0415(11) 0.0466(12) 0.0177(8) -0.0003(8) 0.0098(8) -0.0080(9) C24 0.0354(10) 0.0451(11) 0.0215(9) -0.0003(8) 0.0061(8) -0.0091(8) C25 0.0317(9) 0.0382(10) 0.0244(9) 0.0024(7) 0.0111(7) -0.0043(8) C26 0.0304(9) 0.0348(9) 0.0183(8) 0.0017(7) 0.0094(7) 0.0013(7) C31 0.0348(9) 0.0331(9) 0.0207(8) 0.0007(7) 0.0146(7) 0.0005(7) C32 0.0345(10) 0.0381(10) 0.0238(9) 0.0015(7) 0.0133(8) 0.0017(8) C33 0.0454(11) 0.0384(11) 0.0280(9) 0.0091(8) 0.0201(9) 0.0098(9) C34 0.0517(12) 0.0309(10) 0.0336(10) 0.0011(8) 0.0279(9) -0.0001(9) C35 0.0408(10) 0.0355(10) 0.0269(9) -0.0051(8) 0.0205(8) -0.0058(8) C36 0.0354(10) 0.0349(10) 0.0202(8) 0.0005(7) 0.0141(7) 0.0009(7) C41 0.0284(8) 0.0344(9) 0.0153(7) -0.0016(6) 0.0072(6) -0.0016(7) C42 0.0290(9) 0.0356(10) 0.0191(8) -0.0022(7) 0.0092(7) -0.0032(7) C43 0.0318(9) 0.0334(10) 0.0219(8) -0.0035(7) 0.0069(7) -0.0016(7) C44 0.0291(9) 0.0428(11) 0.0210(8) -0.0068(7) 0.0088(7) 0.0036(8) C45 0.0284(9) 0.0450(11) 0.0193(8) -0.0028(7) 0.0112(7) -0.0037(8) C46 0.0314(9) 0.0355(9) 0.0188(8) -0.0008(7) 0.0105(7) -0.0024(7) C91 0.093(5) 0.092(5) 0.123(6) 0.020(5) 0.056(5) 0.007(4) C92 0.249(9) 0.269(13) 0.205(8) -0.010(10) 0.111(7) -0.015(10) C93 0.084(4) 0.054(3) 0.068(4) -0.011(3) -0.010(3) 0.021(3) C94 0.217(7) 0.283(12) 0.205(8) -0.013(9) 0.083(6) 0.017(9) C95 0.069(4) 0.067(4) 0.089(4) -0.016(4) -0.004(3) 0.028(3) C96 0.174(8) 0.201(11) 0.219(9) 0.028(9) 0.086(6) 0.000(9) C97 0.095(5) 0.046(3) 0.088(5) 0.002(3) 0.012(4) 0.013(3) _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 B C2 1.649(2) . ? B C21 1.652(3) . ? B C31 1.657(3) . ? B C41 1.676(3) . ? F1 C22 1.351(2) . ? F2 C23 1.341(2) . ? F3 C24 1.338(2) . ? F4 C25 1.341(2) . ? F5 C26 1.350(2) . ? F6 C32 1.353(2) . ? F7 C33 1.350(2) . ? F8 C34 1.338(2) . ? F9 C35 1.340(2) . ? F10 C36 1.350(2) . ? F11 C42 1.353(2) . ? F12 C43 1.340(2) . ? F13 C44 1.338(2) . ? F14 C45 1.341(2) . ? F15 C46 1.348(2) . ? N1 C1 1.321(3) . ? N1 C3 1.378(2) . ? N1 C8 1.503(2) . ? N2 C1 1.334(2) . ? N2 C2 1.419(2) . ? N2 C4 1.517(2) . ? C2 C3 1.366(3) . ? C4 C5 1.515(3) . ? C4 C6 1.528(3) . ? C4 C7 1.531(3) . ? C8 C9 1.521(3) . ? C8 C10 1.523(3) . ? C8 C11 1.524(3) . ? C21 C26 1.387(3) . ? C21 C22 1.395(2) . ? C22 C23 1.378(3) . ? C23 C24 1.379(3) . ? C24 C25 1.373(3) . ? C25 C26 1.382(3) . ? C31 C32 1.392(3) . ? C31 C36 1.393(3) . ? C32 C33 1.381(3) . ? C33 C34 1.373(3) . ? C34 C35 1.383(3) . ? C35 C36 1.379(3) . ? C41 C46 1.391(3) . ? C41 C42 1.394(3) . ? C42 C43 1.386(3) . ? C43 C44 1.377(3) . ? C44 C45 1.376(3) . ? C45 C46 1.388(3) . ? C91 C92 1.3900 . ? C91 C96 1.3900 . ? C92 C93 1.3900 . ? C93 C94 1.3900 . ? C94 C97 1.310(13) . ? C94 C95 1.3900 . ? C95 C96 1.3900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 B C21 115.29(15) . . ? C2 B C31 107.98(14) . . ? C21 B C31 114.82(15) . . ? C2 B C41 108.12(15) . . ? C21 B C41 99.49(14) . . ? C31 B C41 110.71(15) . . ? C1 N1 C3 106.91(15) . . ? C1 N1 C8 127.13(15) . . ? C3 N1 C8 125.87(15) . . ? C1 N2 C2 108.48(15) . . ? C1 N2 C4 118.47(15) . . ? C2 N2 C4 132.06(15) . . ? N1 C1 N2 110.57(16) . . ? C3 C2 N2 103.82(15) . . ? C3 C2 B 122.91(16) . . ? N2 C2 B 133.28(16) . . ? C2 C3 N1 110.22(16) . . ? C5 C4 N2 111.98(15) . . ? C5 C4 C6 110.79(18) . . ? N2 C4 C6 106.45(16) . . ? C5 C4 C7 108.18(17) . . ? N2 C4 C7 108.77(16) . . ? C6 C4 C7 110.66(17) . . ? N1 C8 C9 107.68(17) . . ? N1 C8 C10 108.82(16) . . ? C9 C8 C10 110.51(18) . . ? N1 C8 C11 107.67(16) . . ? C9 C8 C11 111.72(19) . . ? C10 C8 C11 110.32(18) . . ? C26 C21 C22 113.36(17) . . ? C26 C21 B 126.07(15) . . ? C22 C21 B 120.02(16) . . ? F1 C22 C23 116.14(16) . . ? F1 C22 C21 119.34(17) . . ? C23 C22 C21 124.52(18) . . ? F2 C23 C22 120.99(19) . . ? F2 C23 C24 119.82(18) . . ? C22 C23 C24 119.18(18) . . ? F3 C24 C25 120.00(19) . . ? F3 C24 C23 120.99(18) . . ? C25 C24 C23 119.01(18) . . ? F4 C25 C24 119.25(18) . . ? F4 C25 C26 120.91(17) . . ? C24 C25 C26 119.82(18) . . ? F5 C26 C25 115.12(16) . . ? F5 C26 C21 120.90(16) . . ? C25 C26 C21 123.97(17) . . ? C32 C31 C36 113.17(18) . . ? C32 C31 B 128.34(17) . . ? C36 C31 B 118.49(16) . . ? F6 C32 C33 115.00(18) . . ? F6 C32 C31 121.05(18) . . ? C33 C32 C31 123.95(19) . . ? F7 C33 C34 119.3(2) . . ? F7 C33 C32 120.5(2) . . ? C34 C33 C32 120.18(19) . . ? F8 C34 C33 121.0(2) . . ? F8 C34 C35 120.3(2) . . ? C33 C34 C35 118.68(19) . . ? F9 C35 C36 121.29(19) . . ? F9 C35 C34 119.54(19) . . ? C36 C35 C34 119.16(19) . . ? F10 C36 C35 115.48(18) . . ? F10 C36 C31 119.63(17) . . ? C35 C36 C31 124.83(19) . . ? C46 C41 C42 112.66(17) . . ? C46 C41 B 126.74(17) . . ? C42 C41 B 119.85(16) . . ? F11 C42 C43 114.79(17) . . ? F11 C42 C41 120.04(17) . . ? C43 C42 C41 125.16(18) . . ? F12 C43 C44 119.92(18) . . ? F12 C43 C42 120.85(18) . . ? C44 C43 C42 119.22(19) . . ? F13 C44 C45 120.83(18) . . ? F13 C44 C43 120.59(19) . . ? C45 C44 C43 118.58(18) . . ? F14 C45 C44 119.73(18) . . ? F14 C45 C46 120.10(19) . . ? C44 C45 C46 120.16(18) . . ? F15 C46 C45 113.84(16) . . ? F15 C46 C41 121.91(17) . . ? C45 C46 C41 124.20(19) . . ? C92 C91 C96 120.0 . . ? C93 C92 C91 120.0 . . ? C92 C93 C94 120.0 . . ? C97 C94 C93 123.9(7) . . ? C97 C94 C95 116.0(7) . . ? C93 C94 C95 120.0 . . ? C96 C95 C94 120.0 . . ? C95 C96 C91 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N1 C1 N2 -0.2(2) . . . . ? C8 N1 C1 N2 -176.94(17) . . . . ? C2 N2 C1 N1 -0.3(2) . . . . ? C4 N2 C1 N1 169.62(17) . . . . ? C1 N2 C2 C3 0.7(2) . . . . ? C4 N2 C2 C3 -167.32(19) . . . . ? C1 N2 C2 B -179.24(19) . . . . ? C4 N2 C2 B 12.7(3) . . . . ? C21 B C2 C3 -115.4(2) . . . . ? C31 B C2 C3 114.68(19) . . . . ? C41 B C2 C3 -5.2(2) . . . . ? C21 B C2 N2 64.6(3) . . . . ? C31 B C2 N2 -65.3(2) . . . . ? C41 B C2 N2 174.84(18) . . . . ? N2 C2 C3 N1 -0.9(2) . . . . ? B C2 C3 N1 179.08(16) . . . . ? C1 N1 C3 C2 0.8(2) . . . . ? C8 N1 C3 C2 177.50(17) . . . . ? C1 N2 C4 C5 153.77(18) . . . . ? C2 N2 C4 C5 -39.1(3) . . . . ? C1 N2 C4 C6 -85.0(2) . . . . ? C2 N2 C4 C6 82.1(2) . . . . ? C1 N2 C4 C7 34.3(2) . . . . ? C2 N2 C4 C7 -158.62(19) . . . . ? C1 N1 C8 C9 102.0(2) . . . . ? C3 N1 C8 C9 -74.1(2) . . . . ? C1 N1 C8 C10 -17.8(3) . . . . ? C3 N1 C8 C10 166.11(19) . . . . ? C1 N1 C8 C11 -137.4(2) . . . . ? C3 N1 C8 C11 46.5(3) . . . . ? C2 B C21 C26 4.8(3) . . . . ? C31 B C21 C26 131.33(19) . . . . ? C41 B C21 C26 -110.5(2) . . . . ? C2 B C21 C22 175.71(17) . . . . ? C31 B C21 C22 -57.8(2) . . . . ? C41 B C21 C22 60.4(2) . . . . ? C26 C21 C22 F1 177.50(18) . . . . ? B C21 C22 F1 5.5(3) . . . . ? C26 C21 C22 C23 -1.5(3) . . . . ? B C21 C22 C23 -173.4(2) . . . . ? F1 C22 C23 F2 -0.4(3) . . . . ? C21 C22 C23 F2 178.6(2) . . . . ? F1 C22 C23 C24 179.8(2) . . . . ? C21 C22 C23 C24 -1.2(4) . . . . ? F2 C23 C24 F3 0.7(4) . . . . ? C22 C23 C24 F3 -179.5(2) . . . . ? F2 C23 C24 C25 -178.4(2) . . . . ? C22 C23 C24 C25 1.4(4) . . . . ? F3 C24 C25 F4 0.7(3) . . . . ? C23 C24 C25 F4 179.8(2) . . . . ? F3 C24 C25 C26 -178.0(2) . . . . ? C23 C24 C25 C26 1.1(3) . . . . ? F4 C25 C26 F5 -3.6(3) . . . . ? C24 C25 C26 F5 175.01(19) . . . . ? F4 C25 C26 C21 177.24(19) . . . . ? C24 C25 C26 C21 -4.1(3) . . . . ? C22 C21 C26 F5 -174.95(17) . . . . ? B C21 C26 F5 -3.6(3) . . . . ? C22 C21 C26 C25 4.1(3) . . . . ? B C21 C26 C25 175.51(19) . . . . ? C2 B C31 C32 122.2(2) . . . . ? C21 B C31 C32 -8.0(3) . . . . ? C41 B C31 C32 -119.6(2) . . . . ? C2 B C31 C36 -58.8(2) . . . . ? C21 B C31 C36 171.08(16) . . . . ? C41 B C31 C36 59.4(2) . . . . ? C36 C31 C32 F6 179.39(16) . . . . ? B C31 C32 F6 -1.5(3) . . . . ? C36 C31 C32 C33 0.0(3) . . . . ? B C31 C32 C33 179.13(18) . . . . ? F6 C32 C33 F7 0.4(3) . . . . ? C31 C32 C33 F7 179.79(18) . . . . ? F6 C32 C33 C34 179.35(17) . . . . ? C31 C32 C33 C34 -1.3(3) . . . . ? F7 C33 C34 F8 0.1(3) . . . . ? C32 C33 C34 F8 -178.83(17) . . . . ? F7 C33 C34 C35 179.97(17) . . . . ? C32 C33 C34 C35 1.0(3) . . . . ? F8 C34 C35 F9 0.7(3) . . . . ? C33 C34 C35 F9 -179.11(17) . . . . ? F8 C34 C35 C36 -179.76(17) . . . . ? C33 C34 C35 C36 0.4(3) . . . . ? F9 C35 C36 F10 0.6(3) . . . . ? C34 C35 C36 F10 -178.87(16) . . . . ? F9 C35 C36 C31 177.75(17) . . . . ? C34 C35 C36 C31 -1.7(3) . . . . ? C32 C31 C36 F10 178.49(15) . . . . ? B C31 C36 F10 -0.7(2) . . . . ? C32 C31 C36 C35 1.5(3) . . . . ? B C31 C36 C35 -177.71(17) . . . . ? C2 B C41 C46 130.49(18) . . . . ? C21 B C41 C46 -108.82(19) . . . . ? C31 B C41 C46 12.4(2) . . . . ? C2 B C41 C42 -60.2(2) . . . . ? C21 B C41 C42 60.51(19) . . . . ? C31 B C41 C42 -178.28(15) . . . . ? C46 C41 C42 F11 177.08(15) . . . . ? B C41 C42 F11 6.3(2) . . . . ? C46 C41 C42 C43 -1.4(3) . . . . ? B C41 C42 C43 -172.12(16) . . . . ? F11 C42 C43 F12 1.5(2) . . . . ? C41 C42 C43 F12 -179.95(16) . . . . ? F11 C42 C43 C44 -177.63(16) . . . . ? C41 C42 C43 C44 0.9(3) . . . . ? F12 C43 C44 F13 0.4(3) . . . . ? C42 C43 C44 F13 179.50(16) . . . . ? F12 C43 C44 C45 -179.16(16) . . . . ? C42 C43 C44 C45 0.0(3) . . . . ? F13 C44 C45 F14 -0.8(3) . . . . ? C43 C44 C45 F14 178.66(16) . . . . ? F13 C44 C45 C46 -179.77(16) . . . . ? C43 C44 C45 C46 -0.3(3) . . . . ? F14 C45 C46 F15 -1.8(2) . . . . ? C44 C45 C46 F15 177.14(16) . . . . ? F14 C45 C46 C41 -179.24(16) . . . . ? C44 C45 C46 C41 -0.3(3) . . . . ? C42 C41 C46 F15 -176.19(16) . . . . ? B C41 C46 F15 -6.2(3) . . . . ? C42 C41 C46 C45 1.1(3) . . . . ? B C41 C46 C45 171.05(17) . . . . ? C96 C91 C92 C93 0.0 . . . . ? C91 C92 C93 C94 0.0 . . . . ? C92 C93 C94 C97 176.5(8) . . . . ? C92 C93 C94 C95 0.0 . . . . ? C97 C94 C95 C96 -176.8(8) . . . . ? C93 C94 C95 C96 0.0 . . . . ? C94 C95 C96 C91 0.0 . . . . ? C92 C91 C96 C95 0.0 . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 70.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.018 _refine_diff_density_min -1.118 _refine_diff_density_rms 0.088 #===END