# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1475 loop_ _publ_author_name 'Kehr, Gerald' 'Erker, G.' 'Frohlich, Roland' 'Schwendemann, Sina' _publ_contact_author_name 'Kehr, Gerald' _publ_contact_author_email kehrald@uni-muenster.de _publ_section_title ; Intramolecular Frustrated N/B Lewis Pairs: Structural Features and Chemistry ; # Attachment '- 5a.cif' data_erk5414 _database_code_depnum_ccdc_archive 'CCDC 815781' #TrackingRef '- 5a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 B F10 N' _chemical_formula_weight 521.20 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 tetragonal _symmetry_space_group_name_H-M P-421c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-y+1/2, -x+1/2, z+1/2' 'y+1/2, x+1/2, z+1/2' _cell_length_a 22.3613(6) _cell_length_b 22.3613(6) _cell_length_c 8.7343(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4367.4(2) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6313 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2112 _exptl_absorpt_coefficient_mu 1.349 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6496 _exptl_absorpt_correction_T_max 0.9115 _exptl_absorpt_process_details 'Denzo (otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33954 _diffrn_reflns_av_R_equivalents 0.066 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.95 _diffrn_reflns_theta_max 67.79 _reflns_number_total 3881 _reflns_number_gt 3572 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0666P)^2^+0.4688P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.45(11) _refine_ls_number_reflns 3881 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.1043 _refine_ls_wR_factor_gt 0.1005 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 N N 0.23836(8) 0.98885(7) 0.88042(19) 0.0357(4) Uani 1 1 d . . . B B 0.25138(11) 0.97525(10) 1.0712(3) 0.0354(5) Uani 1 1 d . . . C1 C 0.29839(9) 1.02460(10) 0.8870(2) 0.0382(5) Uani 1 1 d . . . H1 H 0.2886 1.0662 0.9164 0.046 Uiso 1 1 calc R . . C2 C 0.32013(10) 0.99268(10) 1.0296(3) 0.0400(5) Uani 1 1 d . . . H2A H 0.3390 1.0193 1.1047 0.048 Uiso 1 1 calc R . . H2B H 0.3456 0.9580 1.0083 0.048 Uiso 1 1 calc R . . C11 C 0.24306(11) 0.93434(9) 0.7813(2) 0.0409(5) Uani 1 1 d . . . H11A H 0.2120 0.9060 0.8132 0.049 Uiso 1 1 calc R . . H11B H 0.2818 0.9154 0.8011 0.049 Uiso 1 1 calc R . . C12 C 0.23721(13) 0.94401(12) 0.6093(3) 0.0532(6) Uani 1 1 d . . . H12A H 0.1975 0.9589 0.5861 0.080 Uiso 1 1 calc R . . H12B H 0.2436 0.9064 0.5565 0.080 Uiso 1 1 calc R . . H12C H 0.2668 0.9729 0.5758 0.080 Uiso 1 1 calc R . . C13 C 0.18700(10) 1.02816(10) 0.8356(3) 0.0410(5) Uani 1 1 d . . . H13A H 0.1944 1.0440 0.7328 0.049 Uiso 1 1 calc R . . H13B H 0.1852 1.0622 0.9062 0.049 Uiso 1 1 calc R . . C14 C 0.12659(10) 0.99656(13) 0.8363(3) 0.0550(6) Uani 1 1 d . . . H14A H 0.1274 0.9635 0.7643 0.083 Uiso 1 1 calc R . . H14B H 0.0956 1.0246 0.8067 0.083 Uiso 1 1 calc R . . H14C H 0.1183 0.9815 0.9382 0.083 Uiso 1 1 calc R . . C21 C 0.33670(10) 1.02735(10) 0.7454(2) 0.0405(5) Uani 1 1 d . . . C22 C 0.33041(11) 1.07522(11) 0.6443(3) 0.0477(5) Uani 1 1 d . . . H22 H 0.3022 1.1052 0.6654 0.057 Uiso 1 1 calc R . . C23 C 0.36485(13) 1.07924(13) 0.5141(3) 0.0585(6) Uani 1 1 d . . . H23 H 0.3597 1.1117 0.4471 0.070 Uiso 1 1 calc R . . C24 C 0.40654(14) 1.03629(14) 0.4815(3) 0.0639(8) Uani 1 1 d . . . H24 H 0.4297 1.0389 0.3919 0.077 Uiso 1 1 calc R . . C25 C 0.41438(12) 0.98876(13) 0.5820(3) 0.0587(7) Uani 1 1 d . . . H25 H 0.4434 0.9594 0.5612 0.070 Uiso 1 1 calc R . . C26 C 0.37980(11) 0.98452(11) 0.7119(3) 0.0482(5) Uani 1 1 d . . . H26 H 0.3854 0.9522 0.7790 0.058 Uiso 1 1 calc R . . C41 C 0.21454(10) 1.02150(10) 1.1826(2) 0.0394(5) Uani 1 1 d . . . C42 C 0.23708(11) 1.07553(10) 1.2389(3) 0.0446(5) Uani 1 1 d . . . F42 F 0.28808(7) 1.09880(7) 1.18384(18) 0.0595(4) Uani 1 1 d . . . C43 C 0.20989(14) 1.10882(11) 1.3519(3) 0.0522(6) Uani 1 1 d . . . F43 F 0.23499(9) 1.15925(7) 1.40413(19) 0.0723(5) Uani 1 1 d . . . C44 C 0.15709(13) 1.08976(12) 1.4150(3) 0.0538(6) Uani 1 1 d . . . F44 F 0.13058(9) 1.12117(8) 1.52752(19) 0.0744(5) Uani 1 1 d . . . C45 C 0.13137(12) 1.03787(11) 1.3607(3) 0.0507(6) Uani 1 1 d . . . F45 F 0.07922(8) 1.01908(8) 1.4191(2) 0.0738(5) Uani 1 1 d . . . C46 C 0.15995(10) 1.00620(10) 1.2487(3) 0.0424(5) Uani 1 1 d . . . F46 F 0.13167(6) 0.95558(6) 1.20364(18) 0.0545(4) Uani 1 1 d . . . C31 C 0.24487(9) 0.90704(9) 1.1381(2) 0.0361(4) Uani 1 1 d . . . C32 C 0.20490(9) 0.86117(9) 1.1051(2) 0.0374(5) Uani 1 1 d . . . F32 F 0.16036(6) 0.86917(6) 1.00169(16) 0.0475(3) Uani 1 1 d . . . C33 C 0.20627(10) 0.80552(10) 1.1734(3) 0.0431(5) Uani 1 1 d . . . F33 F 0.16693(6) 0.76314(6) 1.13167(19) 0.0564(4) Uani 1 1 d . . . C34 C 0.24780(11) 0.79322(10) 1.2846(3) 0.0453(5) Uani 1 1 d . . . F34 F 0.24916(8) 0.74002(6) 1.35380(18) 0.0617(4) Uani 1 1 d . . . C35 C 0.28759(10) 0.83720(11) 1.3253(2) 0.0432(5) Uani 1 1 d . . . F35 F 0.32717(7) 0.82767(7) 1.43759(17) 0.0582(4) Uani 1 1 d . . . C36 C 0.28556(10) 0.89182(10) 1.2517(2) 0.0384(4) Uani 1 1 d . . . F36 F 0.32594(6) 0.93226(6) 1.30051(15) 0.0500(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 N 0.0365(8) 0.0343(8) 0.0363(8) 0.0005(7) -0.0004(7) 0.0007(7) B 0.0366(12) 0.0359(11) 0.0337(11) 0.0008(10) -0.0016(10) -0.0006(9) C1 0.0376(11) 0.0375(10) 0.0395(11) -0.0012(9) 0.0005(9) -0.0023(9) C2 0.0378(10) 0.0412(11) 0.0410(11) 0.0012(9) 0.0004(9) -0.0016(9) C11 0.0454(11) 0.0375(10) 0.0400(11) -0.0039(9) -0.0001(10) -0.0012(9) C12 0.0611(14) 0.0553(14) 0.0432(13) -0.0073(11) 0.0015(12) -0.0082(12) C13 0.0440(12) 0.0398(11) 0.0391(11) 0.0043(9) -0.0035(9) 0.0037(9) C14 0.0393(12) 0.0573(14) 0.0684(15) 0.0053(14) -0.0071(12) 0.0062(11) C21 0.0424(11) 0.0413(11) 0.0378(11) -0.0024(9) 0.0026(10) -0.0089(8) C22 0.0514(13) 0.0457(12) 0.0460(12) 0.0031(11) 0.0012(11) -0.0090(10) C23 0.0701(17) 0.0568(15) 0.0487(13) 0.0066(13) 0.0086(13) -0.0184(13) C24 0.0677(17) 0.0745(18) 0.0495(15) -0.0108(14) 0.0228(13) -0.0274(14) C25 0.0504(14) 0.0640(16) 0.0617(15) -0.0165(14) 0.0171(13) -0.0111(12) C26 0.0456(12) 0.0466(13) 0.0524(13) -0.0048(11) 0.0057(11) -0.0043(9) C41 0.0441(11) 0.0409(11) 0.0332(10) 0.0027(9) -0.0002(9) 0.0048(9) C42 0.0550(13) 0.0420(11) 0.0368(11) -0.0001(10) 0.0032(10) -0.0021(10) F42 0.0673(9) 0.0519(8) 0.0593(8) -0.0124(7) 0.0104(8) -0.0164(7) C43 0.0768(17) 0.0411(12) 0.0387(12) -0.0040(10) -0.0024(12) 0.0079(12) F43 0.1079(13) 0.0497(8) 0.0592(9) -0.0187(8) 0.0039(9) -0.0046(9) C44 0.0713(16) 0.0525(14) 0.0376(12) 0.0029(11) 0.0104(12) 0.0208(12) F44 0.1011(13) 0.0641(10) 0.0580(9) -0.0082(8) 0.0223(10) 0.0273(9) C45 0.0523(13) 0.0494(13) 0.0503(13) 0.0077(11) 0.0122(12) 0.0157(11) F45 0.0653(10) 0.0690(10) 0.0870(11) 0.0049(9) 0.0371(9) 0.0116(8) C46 0.0416(11) 0.0394(11) 0.0460(12) 0.0028(10) 0.0005(10) 0.0033(9) F46 0.0424(7) 0.0495(7) 0.0715(9) -0.0032(7) 0.0120(7) -0.0023(6) C31 0.0361(10) 0.0376(10) 0.0345(10) -0.0005(8) 0.0041(9) 0.0046(8) C32 0.0345(10) 0.0411(11) 0.0365(10) 0.0037(9) 0.0041(9) 0.0043(8) F32 0.0405(6) 0.0482(7) 0.0539(7) 0.0069(7) -0.0059(6) -0.0059(5) C33 0.0419(11) 0.0369(10) 0.0505(12) 0.0014(10) 0.0117(10) -0.0002(9) F33 0.0516(8) 0.0428(7) 0.0748(10) 0.0053(7) 0.0100(7) -0.0084(6) C34 0.0544(13) 0.0378(11) 0.0438(12) 0.0084(10) 0.0112(11) 0.0127(10) F34 0.0809(10) 0.0424(7) 0.0617(9) 0.0184(7) 0.0081(8) 0.0104(7) C35 0.0449(11) 0.0506(12) 0.0341(10) 0.0048(10) 0.0021(10) 0.0157(10) F35 0.0629(9) 0.0633(9) 0.0483(8) 0.0104(7) -0.0095(7) 0.0177(7) C36 0.0385(10) 0.0420(11) 0.0348(10) 0.0004(9) 0.0034(9) 0.0041(9) F36 0.0516(7) 0.0548(8) 0.0436(7) 0.0020(6) -0.0082(6) -0.0050(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 N C13 1.498(3) . ? N C11 1.499(3) . ? N C1 1.564(3) . ? N B 1.719(3) . ? B C2 1.627(3) . ? B C31 1.640(3) . ? B C41 1.641(3) . ? C1 C21 1.506(3) . ? C1 C2 1.516(3) . ? C1 H1 0.9900 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C11 C12 1.523(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 H12C 0.9700 . ? C13 C14 1.524(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 H14C 0.9700 . ? C21 C26 1.390(3) . ? C21 C22 1.395(3) . ? C22 C23 1.376(4) . ? C22 H22 0.9400 . ? C23 C24 1.368(4) . ? C23 H23 0.9400 . ? C24 C25 1.390(4) . ? C24 H24 0.9400 . ? C25 C26 1.376(4) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? C41 C46 1.393(3) . ? C41 C42 1.399(3) . ? C42 F42 1.343(3) . ? C42 C43 1.378(3) . ? C43 F43 1.340(3) . ? C43 C44 1.371(4) . ? C44 F44 1.346(3) . ? C44 C45 1.379(4) . ? C45 F45 1.340(3) . ? C45 C46 1.366(3) . ? C46 F46 1.355(3) . ? C31 C36 1.389(3) . ? C31 C32 1.391(3) . ? C32 F32 1.356(3) . ? C32 C33 1.380(3) . ? C33 F33 1.343(3) . ? C33 C34 1.372(4) . ? C34 F34 1.335(3) . ? C34 C35 1.373(4) . ? C35 F35 1.338(3) . ? C35 C36 1.381(3) . ? C36 F36 1.347(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 C13 N C11 112.33(17) . . ? C13 N C1 111.58(15) . . ? C11 N C1 112.13(16) . . ? C13 N B 119.13(16) . . ? C11 N B 113.84(15) . . ? C1 N B 84.81(14) . . ? C2 B C31 112.72(17) . . ? C2 B C41 117.10(18) . . ? C31 B C41 109.29(17) . . ? C2 B N 84.34(15) . . ? C31 B N 119.66(17) . . ? C41 B N 112.21(16) . . ? C21 C1 C2 120.80(18) . . ? C21 C1 N 118.64(17) . . ? C2 C1 N 93.71(16) . . ? C21 C1 H1 107.5 . . ? C2 C1 H1 107.5 . . ? N C1 H1 107.5 . . ? C1 C2 B 89.61(16) . . ? C1 C2 H2A 113.7 . . ? B C2 H2A 113.7 . . ? C1 C2 H2B 113.7 . . ? B C2 H2B 113.7 . . ? H2A C2 H2B 111.0 . . ? N C11 C12 116.62(19) . . ? N C11 H11A 108.1 . . ? C12 C11 H11A 108.1 . . ? N C11 H11B 108.1 . . ? C12 C11 H11B 108.1 . . ? H11A C11 H11B 107.3 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N C13 C14 113.97(19) . . ? N C13 H13A 108.8 . . ? C14 C13 H13A 108.8 . . ? N C13 H13B 108.8 . . ? C14 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C26 C21 C22 117.8(2) . . ? C26 C21 C1 122.6(2) . . ? C22 C21 C1 119.6(2) . . ? C23 C22 C21 121.1(3) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C24 C23 C22 120.5(3) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C25 119.4(2) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? C26 C25 C24 120.2(3) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C25 C26 C21 121.0(2) . . ? C25 C26 H26 119.5 . . ? C21 C26 H26 119.5 . . ? C46 C41 C42 112.4(2) . . ? C46 C41 B 122.1(2) . . ? C42 C41 B 124.9(2) . . ? F42 C42 C43 115.0(2) . . ? F42 C42 C41 121.0(2) . . ? C43 C42 C41 124.1(2) . . ? F43 C43 C44 119.1(2) . . ? F43 C43 C42 120.9(3) . . ? C44 C43 C42 120.0(2) . . ? F44 C44 C43 120.7(3) . . ? F44 C44 C45 120.4(3) . . ? C43 C44 C45 118.9(2) . . ? F45 C45 C46 121.1(2) . . ? F45 C45 C44 119.7(2) . . ? C46 C45 C44 119.2(2) . . ? F46 C46 C45 115.0(2) . . ? F46 C46 C41 119.6(2) . . ? C45 C46 C41 125.4(2) . . ? C36 C31 C32 112.85(19) . . ? C36 C31 B 115.11(19) . . ? C32 C31 B 132.01(19) . . ? F32 C32 C33 115.02(19) . . ? F32 C32 C31 120.84(18) . . ? C33 C32 C31 124.1(2) . . ? F33 C33 C34 119.6(2) . . ? F33 C33 C32 120.3(2) . . ? C34 C33 C32 120.1(2) . . ? F34 C34 C33 121.0(2) . . ? F34 C34 C35 120.4(2) . . ? C33 C34 C35 118.6(2) . . ? F35 C35 C34 120.3(2) . . ? F35 C35 C36 120.3(2) . . ? C34 C35 C36 119.5(2) . . ? F36 C36 C35 115.11(19) . . ? F36 C36 C31 120.05(19) . . ? C35 C36 C31 124.8(2) . . ? 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 C13 N B C2 -131.29(17) . . . . ? C11 N B C2 92.49(18) . . . . ? C1 N B C2 -19.44(14) . . . . ? C13 N B C31 115.7(2) . . . . ? C11 N B C31 -20.5(2) . . . . ? C1 N B C31 -132.40(19) . . . . ? C13 N B C41 -14.3(2) . . . . ? C11 N B C41 -150.51(18) . . . . ? C1 N B C41 97.56(18) . . . . ? C13 N C1 C21 -91.5(2) . . . . ? C11 N C1 C21 35.5(2) . . . . ? B N C1 C21 149.2(2) . . . . ? C13 N C1 C2 140.19(17) . . . . ? C11 N C1 C2 -92.79(18) . . . . ? B N C1 C2 20.86(15) . . . . ? C21 C1 C2 B -148.7(2) . . . . ? N C1 C2 B -22.00(16) . . . . ? C31 B C2 C1 139.83(18) . . . . ? C41 B C2 C1 -92.1(2) . . . . ? N B C2 C1 19.99(14) . . . . ? C13 N C11 C12 45.8(3) . . . . ? C1 N C11 C12 -80.9(2) . . . . ? B N C11 C12 -175.0(2) . . . . ? C11 N C13 C14 56.5(3) . . . . ? C1 N C13 C14 -176.6(2) . . . . ? B N C13 C14 -80.4(2) . . . . ? C2 C1 C21 C26 26.1(3) . . . . ? N C1 C21 C26 -88.2(3) . . . . ? C2 C1 C21 C22 -152.3(2) . . . . ? N C1 C21 C22 93.5(2) . . . . ? C26 C21 C22 C23 1.3(3) . . . . ? C1 C21 C22 C23 179.8(2) . . . . ? C21 C22 C23 C24 -0.5(4) . . . . ? C22 C23 C24 C25 -0.7(4) . . . . ? C23 C24 C25 C26 1.0(4) . . . . ? C24 C25 C26 C21 -0.1(4) . . . . ? C22 C21 C26 C25 -1.1(3) . . . . ? C1 C21 C26 C25 -179.4(2) . . . . ? C2 B C41 C46 -167.8(2) . . . . ? C31 B C41 C46 -38.1(3) . . . . ? N B C41 C46 97.1(2) . . . . ? C2 B C41 C42 2.6(3) . . . . ? C31 B C41 C42 132.3(2) . . . . ? N B C41 C42 -92.5(2) . . . . ? C46 C41 C42 F42 -177.2(2) . . . . ? B C41 C42 F42 11.6(3) . . . . ? C46 C41 C42 C43 2.7(3) . . . . ? B C41 C42 C43 -168.6(2) . . . . ? F42 C42 C43 F43 -2.4(3) . . . . ? C41 C42 C43 F43 177.8(2) . . . . ? F42 C42 C43 C44 179.1(2) . . . . ? C41 C42 C43 C44 -0.8(4) . . . . ? F43 C43 C44 F44 0.1(4) . . . . ? C42 C43 C44 F44 178.7(2) . . . . ? F43 C43 C44 C45 179.9(2) . . . . ? C42 C43 C44 C45 -1.5(4) . . . . ? F44 C44 C45 F45 0.9(4) . . . . ? C43 C44 C45 F45 -178.9(2) . . . . ? F44 C44 C45 C46 -178.6(2) . . . . ? C43 C44 C45 C46 1.7(4) . . . . ? F45 C45 C46 F46 -0.1(3) . . . . ? C44 C45 C46 F46 179.4(2) . . . . ? F45 C45 C46 C41 -179.0(2) . . . . ? C44 C45 C46 C41 0.4(4) . . . . ? C42 C41 C46 F46 178.61(19) . . . . ? B C41 C46 F46 -9.9(3) . . . . ? C42 C41 C46 C45 -2.5(3) . . . . ? B C41 C46 C45 169.0(2) . . . . ? C2 B C31 C36 47.4(3) . . . . ? C41 B C31 C36 -84.6(2) . . . . ? N B C31 C36 144.06(19) . . . . ? C2 B C31 C32 -134.4(2) . . . . ? C41 B C31 C32 93.6(3) . . . . ? N B C31 C32 -37.7(3) . . . . ? C36 C31 C32 F32 177.08(19) . . . . ? B C31 C32 F32 -1.2(3) . . . . ? C36 C31 C32 C33 -2.0(3) . . . . ? B C31 C32 C33 179.7(2) . . . . ? F32 C32 C33 F33 2.7(3) . . . . ? C31 C32 C33 F33 -178.14(19) . . . . ? F32 C32 C33 C34 -177.19(19) . . . . ? C31 C32 C33 C34 2.0(3) . . . . ? F33 C33 C34 F34 -1.0(3) . . . . ? C32 C33 C34 F34 178.9(2) . . . . ? F33 C33 C34 C35 179.9(2) . . . . ? C32 C33 C34 C35 -0.2(3) . . . . ? F34 C34 C35 F35 -1.7(3) . . . . ? C33 C34 C35 F35 177.3(2) . . . . ? F34 C34 C35 C36 179.7(2) . . . . ? C33 C34 C35 C36 -1.3(3) . . . . ? F35 C35 C36 F36 0.8(3) . . . . ? C34 C35 C36 F36 179.34(19) . . . . ? F35 C35 C36 C31 -177.4(2) . . . . ? C34 C35 C36 C31 1.1(3) . . . . ? C32 C31 C36 F36 -177.64(18) . . . . ? B C31 C36 F36 0.9(3) . . . . ? C32 C31 C36 C35 0.5(3) . . . . ? B C31 C36 C35 179.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 67.79 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.186 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.045 # Attachment '- 5c.cif' data_erk4995 _database_code_depnum_ccdc_archive 'CCDC 815782' #TrackingRef '- 5c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H22 B F10 N' _chemical_formula_weight 561.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1677(1) _cell_length_b 11.1135(2) _cell_length_c 13.3821(2) _cell_angle_alpha 68.696(1) _cell_angle_beta 78.909(1) _cell_angle_gamma 81.699(1) _cell_volume 1242.40(3) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3804 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 572 _exptl_absorpt_coefficient_mu 1.229 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6729 _exptl_absorpt_correction_T_max 0.7911 _exptl_absorpt_process_details 'Denzo (otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15451 _diffrn_reflns_av_R_equivalents 0.036 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.28 _diffrn_reflns_theta_max 66.81 _reflns_number_total 4251 _reflns_number_gt 4053 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+0.6644P] 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 4251 _refine_ls_number_parameters 354 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0466 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1184 _refine_ls_wR_factor_gt 0.1171 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 N N 0.07560(15) 0.70993(14) 0.23651(12) 0.0339(3) Uani 1 1 d . . . B B 0.1821(2) 0.82893(18) 0.23023(16) 0.0341(4) Uani 1 1 d . . . C1 C 0.1806(2) 0.69656(18) 0.13359(15) 0.0379(4) Uani 1 1 d . . . H1 H 0.1183 0.7159 0.0760 0.046 Uiso 1 1 calc R . . C2 C 0.26392(19) 0.82009(17) 0.10902(15) 0.0373(4) Uani 1 1 d . . . C3 C 0.4352(2) 0.7966(2) 0.09004(18) 0.0482(5) Uani 1 1 d . . . H3A H 0.4655 0.7612 0.0321 0.072 Uiso 1 1 calc R . . H3B H 0.4686 0.7359 0.1561 0.072 Uiso 1 1 calc R . . H3C H 0.4793 0.8780 0.0700 0.072 Uiso 1 1 calc R . . C4 C 0.2246(2) 0.9199(2) 0.00085(16) 0.0481(5) Uani 1 1 d . . . H4A H 0.2754 0.9975 -0.0168 0.072 Uiso 1 1 calc R . . H4B H 0.1177 0.9418 0.0076 0.072 Uiso 1 1 calc R . . H4C H 0.2559 0.8833 -0.0563 0.072 Uiso 1 1 calc R . . C11 C 0.0435(2) 0.58621(17) 0.33031(15) 0.0399(4) Uani 1 1 d . . . H11A H -0.0106 0.6081 0.3929 0.048 Uiso 1 1 calc R . . H11B H 0.1383 0.5386 0.3502 0.048 Uiso 1 1 calc R . . C12 C -0.0477(2) 0.49816(19) 0.30649(17) 0.0465(5) Uani 1 1 d . . . H12A H 0.0103 0.4687 0.2489 0.056 Uiso 1 1 calc R . . H12B H -0.0670 0.4216 0.3716 0.056 Uiso 1 1 calc R . . C13 C -0.1954(2) 0.5660(2) 0.27169(19) 0.0524(5) Uani 1 1 d . . . H13A H -0.2594 0.5867 0.3319 0.063 Uiso 1 1 calc R . . H13B H -0.2469 0.5091 0.2511 0.063 Uiso 1 1 calc R . . C14 C -0.1646(2) 0.6899(2) 0.17550(18) 0.0478(5) Uani 1 1 d . . . H14A H -0.2592 0.7379 0.1556 0.057 Uiso 1 1 calc R . . H14B H -0.1098 0.6680 0.1131 0.057 Uiso 1 1 calc R . . C15 C -0.07360(19) 0.77457(18) 0.20338(16) 0.0391(4) Uani 1 1 d . . . H15A H -0.0561 0.8536 0.1402 0.047 Uiso 1 1 calc R . . H15B H -0.1323 0.8004 0.2628 0.047 Uiso 1 1 calc R . . C21 C 0.2667(2) 0.56702(18) 0.14456(15) 0.0381(4) Uani 1 1 d . . . C22 C 0.3668(2) 0.5061(2) 0.21889(17) 0.0469(5) Uani 1 1 d . . . H22 H 0.3832 0.5465 0.2660 0.056 Uiso 1 1 calc R . . C23 C 0.4420(3) 0.3865(2) 0.22366(19) 0.0585(6) Uani 1 1 d . . . H23 H 0.5082 0.3465 0.2741 0.070 Uiso 1 1 calc R . . C24 C 0.4196(3) 0.3261(2) 0.1544(2) 0.0651(6) Uani 1 1 d . . . H24 H 0.4701 0.2452 0.1580 0.078 Uiso 1 1 calc R . . C25 C 0.3231(3) 0.3850(2) 0.0804(2) 0.0639(6) Uani 1 1 d . . . H25 H 0.3076 0.3443 0.0333 0.077 Uiso 1 1 calc R . . C26 C 0.2484(2) 0.5046(2) 0.07517(18) 0.0516(5) Uani 1 1 d . . . H26 H 0.1839 0.5443 0.0234 0.062 Uiso 1 1 calc R . . C31 C 0.06991(19) 0.94974(17) 0.25585(15) 0.0367(4) Uani 1 1 d . . . C32 C 0.0494(2) 1.07773(18) 0.18774(17) 0.0441(4) Uani 1 1 d . . . F32 F 0.12219(16) 1.11834(11) 0.08469(10) 0.0587(3) Uani 1 1 d . . . C33 C -0.0442(2) 1.17279(19) 0.2179(2) 0.0520(5) Uani 1 1 d . . . F33 F -0.05997(18) 1.29413(12) 0.14604(13) 0.0750(4) Uani 1 1 d . . . C34 C -0.1224(2) 1.1428(2) 0.3212(2) 0.0523(5) Uani 1 1 d . . . F34 F -0.21633(16) 1.23360(14) 0.35146(14) 0.0742(4) Uani 1 1 d . . . C35 C -0.1051(2) 1.0186(2) 0.39393(17) 0.0466(5) Uani 1 1 d . . . F35 F -0.17830(14) 0.98807(14) 0.49621(11) 0.0625(4) Uani 1 1 d . . . C36 C -0.0104(2) 0.92679(18) 0.36001(16) 0.0396(4) Uani 1 1 d . . . F36 F 0.00265(13) 0.80646(11) 0.43549(9) 0.0485(3) Uani 1 1 d . . . C41 C 0.30776(19) 0.80027(17) 0.31186(14) 0.0358(4) Uani 1 1 d . . . C42 C 0.4028(2) 0.89999(19) 0.27955(16) 0.0439(4) Uani 1 1 d . . . F42 F 0.38362(14) 1.00551(11) 0.19067(10) 0.0558(3) Uani 1 1 d . . . C43 C 0.5172(2) 0.9002(2) 0.33285(19) 0.0529(5) Uani 1 1 d . . . F43 F 0.60506(17) 0.99953(15) 0.29496(13) 0.0796(5) Uani 1 1 d . . . C44 C 0.5427(2) 0.7971(2) 0.42512(18) 0.0520(5) Uani 1 1 d . . . F44 F 0.65507(16) 0.79352(16) 0.47788(13) 0.0785(5) Uani 1 1 d . . . C45 C 0.4511(2) 0.69737(19) 0.46274(15) 0.0426(4) Uani 1 1 d . . . F45 F 0.47165(14) 0.59699(12) 0.55383(9) 0.0565(3) Uani 1 1 d . . . C46 C 0.33706(19) 0.70124(17) 0.40658(15) 0.0367(4) Uani 1 1 d . . . F46 F 0.25308(12) 0.59894(11) 0.45235(9) 0.0471(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 N 0.0294(7) 0.0327(7) 0.0386(8) -0.0107(6) -0.0058(6) -0.0027(6) B 0.0312(10) 0.0291(9) 0.0397(10) -0.0077(8) -0.0078(8) -0.0032(8) C1 0.0351(9) 0.0415(10) 0.0366(9) -0.0131(8) -0.0065(7) -0.0011(7) C2 0.0318(9) 0.0367(9) 0.0412(10) -0.0114(8) -0.0042(7) -0.0031(7) C3 0.0345(10) 0.0524(12) 0.0540(12) -0.0176(9) 0.0013(8) -0.0048(8) C4 0.0489(11) 0.0503(11) 0.0398(10) -0.0097(9) -0.0035(8) -0.0072(9) C11 0.0403(10) 0.0350(9) 0.0406(10) -0.0084(8) -0.0042(8) -0.0062(7) C12 0.0497(11) 0.0378(10) 0.0500(11) -0.0123(8) -0.0014(9) -0.0132(8) C13 0.0425(11) 0.0530(12) 0.0645(13) -0.0203(10) -0.0043(9) -0.0173(9) C14 0.0353(10) 0.0522(12) 0.0589(12) -0.0186(10) -0.0119(9) -0.0079(8) C15 0.0305(9) 0.0384(9) 0.0468(10) -0.0116(8) -0.0089(8) -0.0022(7) C21 0.0360(9) 0.0386(9) 0.0398(9) -0.0152(8) -0.0031(7) -0.0023(7) C22 0.0497(11) 0.0468(11) 0.0468(11) -0.0205(9) -0.0119(9) 0.0054(9) C23 0.0642(14) 0.0526(12) 0.0574(13) -0.0205(10) -0.0177(11) 0.0149(11) C24 0.0766(16) 0.0499(13) 0.0726(15) -0.0314(12) -0.0133(13) 0.0133(12) C25 0.0672(15) 0.0621(14) 0.0775(16) -0.0446(13) -0.0151(12) 0.0075(12) C26 0.0505(12) 0.0592(13) 0.0524(12) -0.0275(10) -0.0124(9) 0.0011(10) C31 0.0334(9) 0.0353(9) 0.0449(10) -0.0147(8) -0.0127(7) -0.0025(7) C32 0.0469(11) 0.0371(10) 0.0512(11) -0.0142(8) -0.0171(9) -0.0025(8) F32 0.0781(9) 0.0399(6) 0.0497(7) -0.0062(5) -0.0115(6) -0.0013(6) C33 0.0553(12) 0.0356(10) 0.0695(14) -0.0182(10) -0.0257(11) 0.0038(9) F33 0.0953(11) 0.0357(7) 0.0912(11) -0.0161(7) -0.0333(9) 0.0135(7) C34 0.0436(11) 0.0462(11) 0.0817(16) -0.0381(11) -0.0202(11) 0.0079(9) F34 0.0647(8) 0.0611(8) 0.1113(12) -0.0539(9) -0.0149(8) 0.0159(7) C35 0.0363(10) 0.0573(12) 0.0576(12) -0.0326(10) -0.0081(9) -0.0038(9) F35 0.0536(7) 0.0782(9) 0.0668(8) -0.0431(7) 0.0017(6) -0.0063(6) C36 0.0361(9) 0.0371(9) 0.0497(10) -0.0170(8) -0.0128(8) -0.0024(7) F36 0.0488(6) 0.0460(6) 0.0458(6) -0.0124(5) -0.0033(5) -0.0028(5) C41 0.0312(9) 0.0363(9) 0.0396(9) -0.0132(7) -0.0060(7) -0.0009(7) C42 0.0403(10) 0.0432(10) 0.0462(11) -0.0101(8) -0.0104(8) -0.0063(8) F42 0.0561(7) 0.0436(6) 0.0615(7) -0.0005(5) -0.0203(6) -0.0162(5) C43 0.0436(11) 0.0559(12) 0.0608(13) -0.0148(10) -0.0122(10) -0.0177(9) F43 0.0723(9) 0.0781(10) 0.0882(11) -0.0058(8) -0.0314(8) -0.0406(8) C44 0.0394(11) 0.0673(14) 0.0541(12) -0.0207(11) -0.0171(9) -0.0068(10) F44 0.0625(9) 0.0975(11) 0.0797(10) -0.0152(8) -0.0392(8) -0.0231(8) C45 0.0395(10) 0.0485(11) 0.0387(10) -0.0132(8) -0.0115(8) 0.0021(8) F45 0.0595(7) 0.0618(8) 0.0453(6) -0.0084(6) -0.0239(6) -0.0013(6) C46 0.0321(9) 0.0393(9) 0.0385(9) -0.0141(8) -0.0037(7) -0.0032(7) F46 0.0491(6) 0.0449(6) 0.0425(6) -0.0044(5) -0.0120(5) -0.0112(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 N C11 1.508(2) . ? N C15 1.517(2) . ? N C1 1.563(2) . ? N B 1.723(2) . ? B C41 1.657(3) . ? B C31 1.667(3) . ? B C2 1.682(3) . ? C1 C21 1.510(3) . ? C1 C2 1.567(3) . ? C1 H1 0.9900 . ? C2 C4 1.541(3) . ? C2 C3 1.541(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 H3C 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C4 H4C 0.9700 . ? C11 C12 1.524(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C12 C13 1.520(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C13 C14 1.522(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C14 C15 1.524(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C21 C26 1.391(3) . ? C21 C22 1.404(3) . ? C22 C23 1.392(3) . ? C22 H22 0.9400 . ? C23 C24 1.384(3) . ? C23 H23 0.9400 . ? C24 C25 1.375(4) . ? C24 H24 0.9400 . ? C25 C26 1.388(3) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? C31 C32 1.391(3) . ? C31 C36 1.397(3) . ? C32 F32 1.353(2) . ? C32 C33 1.389(3) . ? C33 F33 1.349(2) . ? C33 C34 1.374(3) . ? C34 F34 1.354(2) . ? C34 C35 1.378(3) . ? C35 F35 1.347(2) . ? C35 C36 1.389(3) . ? C36 F36 1.357(2) . ? C41 C46 1.386(3) . ? C41 C42 1.400(3) . ? C42 F42 1.352(2) . ? C42 C43 1.378(3) . ? C43 F43 1.348(2) . ? C43 C44 1.378(3) . ? C44 F44 1.345(2) . ? C44 C45 1.373(3) . ? C45 F45 1.344(2) . ? C45 C46 1.388(3) . ? C46 F46 1.351(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 C11 N C15 106.68(13) . . ? C11 N C1 116.79(13) . . ? C15 N C1 108.16(13) . . ? C11 N B 127.34(13) . . ? C15 N B 107.92(12) . . ? C1 N B 88.07(12) . . ? C41 B C31 102.85(14) . . ? C41 B C2 110.60(14) . . ? C31 B C2 128.17(15) . . ? C41 B N 121.87(14) . . ? C31 B N 109.10(13) . . ? C2 B N 85.54(12) . . ? C21 C1 N 117.37(14) . . ? C21 C1 C2 120.68(15) . . ? N C1 C2 95.30(13) . . ? C21 C1 H1 107.5 . . ? N C1 H1 107.5 . . ? C2 C1 H1 107.5 . . ? C4 C2 C3 104.83(15) . . ? C4 C2 C1 107.61(15) . . ? C3 C2 C1 113.81(15) . . ? C4 C2 B 122.57(15) . . ? C3 C2 B 117.60(15) . . ? C1 C2 B 89.44(13) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N C11 C12 113.83(15) . . ? N C11 H11A 108.8 . . ? C12 C11 H11A 108.8 . . ? N C11 H11B 108.8 . . ? C12 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C13 C12 C11 112.29(17) . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12B 109.1 . . ? C11 C12 H12B 109.1 . . ? H12A C12 H12B 107.9 . . ? C12 C13 C14 108.68(16) . . ? C12 C13 H13A 110.0 . . ? C14 C13 H13A 110.0 . . ? C12 C13 H13B 110.0 . . ? C14 C13 H13B 110.0 . . ? H13A C13 H13B 108.3 . . ? C13 C14 C15 110.58(17) . . ? C13 C14 H14A 109.5 . . ? C15 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? N C15 C14 114.35(15) . . ? N C15 H15A 108.7 . . ? C14 C15 H15A 108.7 . . ? N C15 H15B 108.7 . . ? C14 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C26 C21 C22 117.51(18) . . ? C26 C21 C1 118.08(17) . . ? C22 C21 C1 124.40(17) . . ? C23 C22 C21 120.76(19) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C24 C23 C22 120.2(2) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C25 C24 C23 119.7(2) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C24 C25 C26 120.2(2) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C25 C26 C21 121.6(2) . . ? C25 C26 H26 119.2 . . ? C21 C26 H26 119.2 . . ? C32 C31 C36 112.88(17) . . ? C32 C31 B 128.49(17) . . ? C36 C31 B 118.52(15) . . ? F32 C32 C33 114.86(17) . . ? F32 C32 C31 120.97(17) . . ? C33 C32 C31 124.2(2) . . ? F33 C33 C34 119.74(19) . . ? F33 C33 C32 120.4(2) . . ? C34 C33 C32 119.89(19) . . ? F34 C34 C33 120.7(2) . . ? F34 C34 C35 120.1(2) . . ? C33 C34 C35 119.18(19) . . ? F35 C35 C34 120.08(18) . . ? F35 C35 C36 121.05(19) . . ? C34 C35 C36 118.9(2) . . ? F36 C36 C35 116.10(18) . . ? F36 C36 C31 118.93(16) . . ? C35 C36 C31 124.98(18) . . ? C46 C41 C42 112.92(16) . . ? C46 C41 B 134.24(16) . . ? C42 C41 B 112.82(15) . . ? F42 C42 C43 115.89(17) . . ? F42 C42 C41 119.50(16) . . ? C43 C42 C41 124.60(19) . . ? F43 C43 C44 119.89(18) . . ? F43 C43 C42 120.6(2) . . ? C44 C43 C42 119.46(19) . . ? F44 C44 C45 120.28(19) . . ? F44 C44 C43 120.82(19) . . ? C45 C44 C43 118.90(18) . . ? F45 C45 C44 120.02(17) . . ? F45 C45 C46 120.29(17) . . ? C44 C45 C46 119.69(18) . . ? F46 C46 C41 121.35(16) . . ? F46 C46 C45 114.27(16) . . ? C41 C46 C45 124.38(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 C11 N B C41 20.6(2) . . . . ? C15 N B C41 149.30(16) . . . . ? C1 N B C41 -102.23(17) . . . . ? C11 N B C31 -98.94(18) . . . . ? C15 N B C31 29.81(18) . . . . ? C1 N B C31 138.28(14) . . . . ? C11 N B C2 132.09(16) . . . . ? C15 N B C2 -99.17(14) . . . . ? C1 N B C2 9.30(12) . . . . ? C11 N C1 C21 -12.8(2) . . . . ? C15 N C1 C21 -133.08(16) . . . . ? B N C1 C21 118.68(16) . . . . ? C11 N C1 C2 -141.52(14) . . . . ? C15 N C1 C2 98.22(14) . . . . ? B N C1 C2 -10.01(13) . . . . ? C21 C1 C2 C4 119.79(18) . . . . ? N C1 C2 C4 -113.92(15) . . . . ? C21 C1 C2 C3 4.1(2) . . . . ? N C1 C2 C3 130.39(16) . . . . ? C21 C1 C2 B -116.04(17) . . . . ? N C1 C2 B 10.25(13) . . . . ? C41 B C2 C4 -136.19(17) . . . . ? C31 B C2 C4 -9.5(3) . . . . ? N B C2 C4 101.37(17) . . . . ? C41 B C2 C3 -3.6(2) . . . . ? C31 B C2 C3 123.08(19) . . . . ? N B C2 C3 -126.05(16) . . . . ? C41 B C2 C1 113.16(15) . . . . ? C31 B C2 C1 -120.15(18) . . . . ? N B C2 C1 -9.28(12) . . . . ? C15 N C11 C12 54.19(19) . . . . ? C1 N C11 C12 -66.9(2) . . . . ? B N C11 C12 -176.59(15) . . . . ? N C11 C12 C13 -56.9(2) . . . . ? C11 C12 C13 C14 54.8(2) . . . . ? C12 C13 C14 C15 -55.1(2) . . . . ? C11 N C15 C14 -55.8(2) . . . . ? C1 N C15 C14 70.55(18) . . . . ? B N C15 C14 164.49(15) . . . . ? C13 C14 C15 N 58.7(2) . . . . ? N C1 C21 C26 122.98(19) . . . . ? C2 C1 C21 C26 -121.7(2) . . . . ? N C1 C21 C22 -58.4(2) . . . . ? C2 C1 C21 C22 57.0(3) . . . . ? C26 C21 C22 C23 -1.2(3) . . . . ? C1 C21 C22 C23 -179.91(19) . . . . ? C21 C22 C23 C24 0.4(4) . . . . ? C22 C23 C24 C25 0.3(4) . . . . ? C23 C24 C25 C26 0.0(4) . . . . ? C24 C25 C26 C21 -0.9(4) . . . . ? C22 C21 C26 C25 1.5(3) . . . . ? C1 C21 C26 C25 -179.7(2) . . . . ? C41 B C31 C32 112.46(19) . . . . ? C2 B C31 C32 -17.2(3) . . . . ? N B C31 C32 -116.85(19) . . . . ? C41 B C31 C36 -63.51(19) . . . . ? C2 B C31 C36 166.83(17) . . . . ? N B C31 C36 67.18(19) . . . . ? C36 C31 C32 F32 178.03(16) . . . . ? B C31 C32 F32 1.9(3) . . . . ? C36 C31 C32 C33 -1.9(3) . . . . ? B C31 C32 C33 -178.04(18) . . . . ? F32 C32 C33 F33 1.4(3) . . . . ? C31 C32 C33 F33 -178.65(18) . . . . ? F32 C32 C33 C34 -179.22(18) . . . . ? C31 C32 C33 C34 0.7(3) . . . . ? F33 C33 C34 F34 0.6(3) . . . . ? C32 C33 C34 F34 -178.76(18) . . . . ? F33 C33 C34 C35 -179.83(18) . . . . ? C32 C33 C34 C35 0.8(3) . . . . ? F34 C34 C35 F35 -1.8(3) . . . . ? C33 C34 C35 F35 178.60(18) . . . . ? F34 C34 C35 C36 178.64(17) . . . . ? C33 C34 C35 C36 -0.9(3) . . . . ? F35 C35 C36 F36 0.1(3) . . . . ? C34 C35 C36 F36 179.65(16) . . . . ? F35 C35 C36 C31 -179.96(17) . . . . ? C34 C35 C36 C31 -0.4(3) . . . . ? C32 C31 C36 F36 -178.32(15) . . . . ? B C31 C36 F36 -1.7(2) . . . . ? C32 C31 C36 C35 1.8(3) . . . . ? B C31 C36 C35 178.33(17) . . . . ? C31 B C41 C46 107.9(2) . . . . ? C2 B C41 C46 -112.4(2) . . . . ? N B C41 C46 -14.5(3) . . . . ? C31 B C41 C42 -69.95(18) . . . . ? C2 B C41 C42 69.76(19) . . . . ? N B C41 C42 167.57(16) . . . . ? C46 C41 C42 F42 -177.51(17) . . . . ? B C41 C42 F42 0.8(3) . . . . ? C46 C41 C42 C43 1.9(3) . . . . ? B C41 C42 C43 -179.7(2) . . . . ? F42 C42 C43 F43 -1.6(3) . . . . ? C41 C42 C43 F43 178.9(2) . . . . ? F42 C42 C43 C44 179.0(2) . . . . ? C41 C42 C43 C44 -0.4(4) . . . . ? F43 C43 C44 F44 -0.4(4) . . . . ? C42 C43 C44 F44 178.9(2) . . . . ? F43 C43 C44 C45 179.5(2) . . . . ? C42 C43 C44 C45 -1.2(3) . . . . ? F44 C44 C45 F45 1.4(3) . . . . ? C43 C44 C45 F45 -178.60(19) . . . . ? F44 C44 C45 C46 -178.97(19) . . . . ? C43 C44 C45 C46 1.1(3) . . . . ? C42 C41 C46 F46 177.55(16) . . . . ? B C41 C46 F46 -0.3(3) . . . . ? C42 C41 C46 C45 -2.0(3) . . . . ? B C41 C46 C45 -179.90(18) . . . . ? F45 C45 C46 F46 0.7(3) . . . . ? C44 C45 C46 F46 -178.98(18) . . . . ? F45 C45 C46 C41 -179.71(17) . . . . ? C44 C45 C46 C41 0.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 66.81 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.242 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.038 # Attachment '- 5d.cif' data_erk5393 _database_code_depnum_ccdc_archive 'CCDC 815783' #TrackingRef '- 5d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H20 B F10 N' _chemical_formula_weight 511.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.5936(9) _cell_length_b 9.2952(6) _cell_length_c 26.1791(17) _cell_angle_alpha 90.00 _cell_angle_beta 104.988(3) _cell_angle_gamma 90.00 _cell_volume 4370.6(5) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2885 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description plate _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080 _exptl_absorpt_coefficient_mu 1.332 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8252 _exptl_absorpt_correction_T_max 0.9611 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18687 _diffrn_reflns_av_R_equivalents 0.102 _diffrn_reflns_av_sigmaI/netI 0.0709 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 4.92 _diffrn_reflns_theta_max 67.30 _reflns_number_total 3044 _reflns_number_gt 1876 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+7.4531P] 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 3044 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1085 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1434 _refine_ls_wR_factor_gt 0.1251 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 N N 0.20275(17) -0.4272(4) -0.14235(12) 0.0573(9) Uani 1 1 d . . . B B 0.1200(2) -0.4541(6) -0.11827(18) 0.0588(14) Uani 1 1 d . . . C1 C 0.1857(2) -0.5792(5) -0.16184(16) 0.0574(11) Uani 1 1 d . . . H1 H 0.2081 -0.6428 -0.1316 0.069 Uiso 1 1 calc R . . C2 C 0.1031(2) -0.5741(5) -0.16552(16) 0.0610(12) Uani 1 1 d . . . H2 H 0.0773 -0.5265 -0.1991 0.073 Uiso 1 1 calc R . . C11 C 0.1858(2) -0.3207(5) -0.18779(17) 0.0667(13) Uani 1 1 d . . . H11A H 0.2123 -0.3505 -0.2139 0.080 Uiso 1 1 calc R . . H11B H 0.1324 -0.3237 -0.2050 0.080 Uiso 1 1 calc R . . C12 C 0.2074(3) -0.1683(6) -0.17121(19) 0.0739(14) Uani 1 1 d . . . H12A H 0.1762 -0.1335 -0.1489 0.089 Uiso 1 1 calc R . . H12B H 0.1980 -0.1071 -0.2027 0.089 Uiso 1 1 calc R . . C13 C 0.2885(3) -0.1545(6) -0.14113(19) 0.0807(15) Uani 1 1 d . . . H13A H 0.2988 -0.0561 -0.1278 0.097 Uiso 1 1 calc R . . H13B H 0.3205 -0.1755 -0.1647 0.097 Uiso 1 1 calc R . . C14 C 0.3049(2) -0.2599(6) -0.09515(19) 0.0790(15) Uani 1 1 d . . . H14A H 0.2767 -0.2326 -0.0698 0.095 Uiso 1 1 calc R . . H14B H 0.3580 -0.2568 -0.0769 0.095 Uiso 1 1 calc R . . C15 C 0.2835(2) -0.4115(6) -0.11527(18) 0.0675(13) Uani 1 1 d . . . H15A H 0.3128 -0.4384 -0.1400 0.081 Uiso 1 1 calc R . . H15B H 0.2963 -0.4785 -0.0854 0.081 Uiso 1 1 calc R . . C21 C 0.2058(2) -0.6428(6) -0.20924(17) 0.0723(14) Uani 1 1 d . . . H21A H 0.2599 -0.6414 -0.2045 0.087 Uiso 1 1 calc R . . H21B H 0.1819 -0.5896 -0.2415 0.087 Uiso 1 1 calc R . . C22 C 0.1769(3) -0.7968(6) -0.2122(2) 0.0762(14) Uani 1 1 d . . . H22A H 0.2068 -0.8508 -0.1819 0.091 Uiso 1 1 calc R . . H22B H 0.1838 -0.8419 -0.2444 0.091 Uiso 1 1 calc R . . C23 C 0.0950(2) -0.8081(6) -0.21221(18) 0.0794(15) Uani 1 1 d . . . H23A H 0.0822 -0.9099 -0.2105 0.095 Uiso 1 1 calc R . . H23B H 0.0646 -0.7696 -0.2457 0.095 Uiso 1 1 calc R . . C24 C 0.0748(2) -0.7278(6) -0.16626(17) 0.0730(14) Uani 1 1 d . . . H24A H 0.0207 -0.7281 -0.1713 0.088 Uiso 1 1 calc R . . H24B H 0.0979 -0.7755 -0.1326 0.088 Uiso 1 1 calc R . . C31 C 0.1296(2) -0.5314(5) -0.06084(15) 0.0551(11) Uani 1 1 d . . . C32 C 0.1891(2) -0.5518(5) -0.01819(16) 0.0620(12) Uani 1 1 d . . . F32 F 0.25701(13) -0.4991(3) -0.01798(9) 0.0852(9) Uani 1 1 d . . . C33 C 0.1861(3) -0.6230(5) 0.02767(16) 0.0674(13) Uani 1 1 d . . . F33 F 0.24836(16) -0.6387(4) 0.06703(10) 0.0976(9) Uani 1 1 d . . . C34 C 0.1200(3) -0.6763(6) 0.03234(18) 0.0740(14) Uani 1 1 d . . . F34 F 0.11671(18) -0.7466(4) 0.07653(11) 0.1069(10) Uani 1 1 d . . . C35 C 0.0577(3) -0.6581(5) -0.00827(19) 0.0676(13) Uani 1 1 d . . . F35 F -0.00833(16) -0.7074(4) -0.00415(12) 0.0997(10) Uani 1 1 d . . . C36 C 0.0638(2) -0.5859(5) -0.05323(17) 0.0619(12) Uani 1 1 d . . . F36 F -0.00042(12) -0.5695(3) -0.09137(9) 0.0790(8) Uani 1 1 d . . . C41 C 0.0738(2) -0.3062(5) -0.12037(16) 0.0552(11) Uani 1 1 d . . . C42 C 0.0090(2) -0.2723(6) -0.15843(17) 0.0672(13) Uani 1 1 d . . . F42 F -0.02024(14) -0.3640(4) -0.19841(10) 0.0921(9) Uani 1 1 d . . . C43 C -0.0299(2) -0.1442(7) -0.1582(2) 0.0741(14) Uani 1 1 d . . . F43 F -0.09220(15) -0.1179(4) -0.19631(12) 0.1068(11) Uani 1 1 d . . . C44 C -0.0054(3) -0.0494(6) -0.1182(2) 0.0767(15) Uani 1 1 d . . . F44 F -0.04351(15) 0.0743(4) -0.11674(14) 0.1073(11) Uani 1 1 d . . . C45 C 0.0570(3) -0.0792(6) -0.0788(2) 0.0721(14) Uani 1 1 d . . . F45 F 0.08037(15) 0.0146(3) -0.03895(14) 0.1022(10) Uani 1 1 d . . . C46 C 0.0945(2) -0.2046(6) -0.08103(17) 0.0606(12) Uani 1 1 d . . . F46 F 0.15609(13) -0.2278(3) -0.04145(10) 0.0778(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N 0.0486(19) 0.076(3) 0.048(2) 0.008(2) 0.0137(15) -0.0004(19) B 0.048(3) 0.080(4) 0.049(3) 0.003(3) 0.013(2) 0.001(3) C1 0.054(2) 0.069(3) 0.050(2) 0.003(2) 0.015(2) -0.001(2) C2 0.049(2) 0.091(4) 0.044(2) 0.004(2) 0.0144(19) -0.002(2) C11 0.058(3) 0.089(4) 0.055(3) 0.008(3) 0.018(2) 0.002(3) C12 0.078(3) 0.083(4) 0.066(3) 0.007(3) 0.028(3) -0.002(3) C13 0.084(3) 0.089(4) 0.078(3) -0.003(3) 0.038(3) -0.016(3) C14 0.054(3) 0.117(5) 0.067(3) -0.006(3) 0.017(2) -0.012(3) C15 0.044(2) 0.095(4) 0.064(3) 0.005(3) 0.015(2) 0.003(3) C21 0.065(3) 0.096(4) 0.061(3) -0.007(3) 0.026(2) 0.002(3) C22 0.080(3) 0.080(4) 0.074(3) -0.011(3) 0.030(3) -0.002(3) C23 0.075(3) 0.098(4) 0.069(3) -0.014(3) 0.026(3) -0.011(3) C24 0.060(3) 0.100(4) 0.059(3) -0.012(3) 0.017(2) -0.007(3) C31 0.052(2) 0.069(3) 0.046(2) 0.001(2) 0.015(2) -0.002(2) C32 0.053(3) 0.081(3) 0.051(3) 0.003(3) 0.012(2) -0.002(2) F32 0.0594(15) 0.128(2) 0.0619(16) 0.0112(16) 0.0050(12) -0.0103(16) C33 0.077(3) 0.083(3) 0.040(3) 0.009(3) 0.010(2) 0.010(3) F33 0.097(2) 0.136(3) 0.0526(15) 0.0184(17) 0.0064(15) 0.0182(19) C34 0.096(4) 0.086(4) 0.050(3) 0.014(3) 0.038(3) 0.006(3) F34 0.135(2) 0.123(3) 0.0755(19) 0.0305(19) 0.0500(17) 0.008(2) C35 0.065(3) 0.081(4) 0.065(3) 0.005(3) 0.033(3) -0.003(3) F35 0.090(2) 0.129(3) 0.096(2) 0.0070(19) 0.0530(16) -0.0184(18) C36 0.055(3) 0.082(3) 0.050(3) -0.002(3) 0.016(2) 0.005(3) F36 0.0552(14) 0.119(2) 0.0648(15) 0.0037(15) 0.0191(13) -0.0048(14) C41 0.045(2) 0.077(3) 0.045(2) 0.009(2) 0.014(2) 0.001(2) C42 0.056(3) 0.098(4) 0.048(3) 0.002(3) 0.015(2) 0.006(3) F42 0.0675(16) 0.137(3) 0.0617(16) -0.0091(18) -0.0020(13) 0.0219(17) C43 0.051(3) 0.099(4) 0.073(3) 0.012(3) 0.016(3) 0.013(3) F43 0.0676(17) 0.144(3) 0.100(2) 0.023(2) 0.0064(16) 0.0391(19) C44 0.052(3) 0.083(4) 0.103(4) 0.017(4) 0.035(3) 0.018(3) F44 0.0723(18) 0.097(2) 0.163(3) 0.017(2) 0.0481(19) 0.0175(18) C45 0.058(3) 0.081(4) 0.085(4) -0.008(3) 0.031(3) -0.008(3) F45 0.0784(19) 0.092(2) 0.137(3) -0.031(2) 0.0301(18) 0.0037(16) C46 0.044(2) 0.084(4) 0.055(3) 0.003(3) 0.015(2) 0.005(3) F46 0.0646(15) 0.091(2) 0.0704(16) -0.0111(15) 0.0047(13) 0.0043(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 N C15 1.493(5) . ? N C1 1.508(6) . ? N C11 1.517(5) . ? N B 1.824(6) . ? B C41 1.615(7) . ? B C31 1.634(6) . ? B C2 1.634(7) . ? C1 C21 1.507(6) . ? C1 C2 1.514(5) . ? C1 H1 0.9900 . ? C2 C24 1.521(7) . ? C2 H2 0.9900 . ? C11 C12 1.506(7) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C12 C13 1.515(6) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C13 C14 1.520(7) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C14 C15 1.521(7) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C21 C22 1.524(7) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C22 C23 1.526(6) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C23 C24 1.543(6) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C31 C32 1.367(5) . ? C31 C36 1.385(5) . ? C32 F32 1.353(5) . ? C32 C33 1.385(6) . ? C33 F33 1.343(5) . ? C33 C34 1.359(6) . ? C34 F34 1.344(5) . ? C34 C35 1.365(6) . ? C35 F35 1.341(5) . ? C35 C36 1.385(6) . ? C36 F36 1.352(4) . ? C41 C46 1.376(6) . ? C41 C42 1.387(6) . ? C42 F42 1.350(5) . ? C42 C43 1.394(7) . ? C43 F43 1.341(5) . ? C43 C44 1.355(7) . ? C44 F44 1.357(6) . ? C44 C45 1.367(7) . ? C45 F45 1.342(5) . ? C45 C46 1.368(7) . ? C46 F46 1.348(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 C15 N C1 110.5(3) . . ? C15 N C11 106.7(3) . . ? C1 N C11 111.3(3) . . ? C15 N B 133.1(3) . . ? C1 N B 82.3(3) . . ? C11 N B 109.8(3) . . ? C41 B C31 109.6(3) . . ? C41 B C2 124.0(4) . . ? C31 B C2 110.5(4) . . ? C41 B N 111.1(4) . . ? C31 B N 118.5(3) . . ? C2 B N 81.2(3) . . ? C21 C1 N 124.8(4) . . ? C21 C1 C2 115.1(3) . . ? N C1 C2 96.5(3) . . ? C21 C1 H1 106.3 . . ? N C1 H1 106.3 . . ? C2 C1 H1 106.3 . . ? C1 C2 C24 108.2(4) . . ? C1 C2 B 88.8(3) . . ? C24 C2 B 130.4(4) . . ? C1 C2 H2 108.8 . . ? C24 C2 H2 108.8 . . ? B C2 H2 108.8 . . ? C12 C11 N 113.7(4) . . ? C12 C11 H11A 108.8 . . ? N C11 H11A 108.8 . . ? C12 C11 H11B 108.8 . . ? N C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C11 C12 C13 112.6(4) . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C12 C13 C14 109.0(4) . . ? C12 C13 H13A 109.9 . . ? C14 C13 H13A 109.9 . . ? C12 C13 H13B 109.9 . . ? C14 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? C13 C14 C15 110.0(4) . . ? C13 C14 H14A 109.7 . . ? C15 C14 H14A 109.7 . . ? C13 C14 H14B 109.7 . . ? C15 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? N C15 C14 113.3(4) . . ? N C15 H15A 108.9 . . ? C14 C15 H15A 108.9 . . ? N C15 H15B 108.9 . . ? C14 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? C1 C21 C22 104.5(4) . . ? C1 C21 H21A 110.9 . . ? C22 C21 H21A 110.9 . . ? C1 C21 H21B 110.9 . . ? C22 C21 H21B 110.9 . . ? H21A C21 H21B 108.9 . . ? C21 C22 C23 113.8(4) . . ? C21 C22 H22A 108.8 . . ? C23 C22 H22A 108.8 . . ? C21 C22 H22B 108.8 . . ? C23 C22 H22B 108.8 . . ? H22A C22 H22B 107.7 . . ? C22 C23 C24 114.2(4) . . ? C22 C23 H23A 108.7 . . ? C24 C23 H23A 108.7 . . ? C22 C23 H23B 108.7 . . ? C24 C23 H23B 108.7 . . ? H23A C23 H23B 107.6 . . ? C2 C24 C23 108.1(4) . . ? C2 C24 H24A 110.1 . . ? C23 C24 H24A 110.1 . . ? C2 C24 H24B 110.1 . . ? C23 C24 H24B 110.1 . . ? H24A C24 H24B 108.4 . . ? C32 C31 C36 113.0(4) . . ? C32 C31 B 133.2(4) . . ? C36 C31 B 113.8(3) . . ? F32 C32 C31 120.7(4) . . ? F32 C32 C33 114.6(4) . . ? C31 C32 C33 124.7(4) . . ? F33 C33 C34 120.7(4) . . ? F33 C33 C32 119.8(4) . . ? C34 C33 C32 119.5(4) . . ? F34 C34 C33 119.9(5) . . ? F34 C34 C35 120.8(5) . . ? C33 C34 C35 119.3(4) . . ? F35 C35 C34 120.4(4) . . ? F35 C35 C36 120.8(4) . . ? C34 C35 C36 118.9(4) . . ? F36 C36 C35 115.6(4) . . ? F36 C36 C31 119.8(4) . . ? C35 C36 C31 124.6(4) . . ? C46 C41 C42 113.9(4) . . ? C46 C41 B 121.0(4) . . ? C42 C41 B 125.0(4) . . ? F42 C42 C41 121.0(5) . . ? F42 C42 C43 115.9(4) . . ? C41 C42 C43 123.1(5) . . ? F43 C43 C44 120.6(5) . . ? F43 C43 C42 120.1(5) . . ? C44 C43 C42 119.2(4) . . ? C43 C44 F44 119.9(5) . . ? C43 C44 C45 120.2(5) . . ? F44 C44 C45 119.9(6) . . ? F45 C45 C44 119.7(5) . . ? F45 C45 C46 121.4(5) . . ? C44 C45 C46 118.9(5) . . ? F46 C46 C45 116.4(4) . . ? F46 C46 C41 118.9(4) . . ? C45 C46 C41 124.7(4) . . ? 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 C15 N B C41 102.5(5) . . . . ? C1 N B C41 -146.5(3) . . . . ? C11 N B C41 -36.6(4) . . . . ? C15 N B C31 -25.8(7) . . . . ? C1 N B C31 85.2(4) . . . . ? C11 N B C31 -164.9(4) . . . . ? C15 N B C2 -134.4(5) . . . . ? C1 N B C2 -23.4(3) . . . . ? C11 N B C2 86.5(4) . . . . ? C15 N C1 C21 -74.6(5) . . . . ? C11 N C1 C21 43.8(5) . . . . ? B N C1 C21 152.1(4) . . . . ? C15 N C1 C2 158.6(3) . . . . ? C11 N C1 C2 -83.0(4) . . . . ? B N C1 C2 25.3(3) . . . . ? C21 C1 C2 C24 65.8(5) . . . . ? N C1 C2 C24 -160.8(3) . . . . ? C21 C1 C2 B -161.7(4) . . . . ? N C1 C2 B -28.2(3) . . . . ? C41 B C2 C1 132.7(4) . . . . ? C31 B C2 C1 -94.1(4) . . . . ? N B C2 C1 23.1(3) . . . . ? C41 B C2 C24 -114.1(5) . . . . ? C31 B C2 C24 19.1(6) . . . . ? N B C2 C24 136.3(4) . . . . ? C15 N C11 C12 -54.8(5) . . . . ? C1 N C11 C12 -175.5(3) . . . . ? B N C11 C12 95.3(4) . . . . ? N C11 C12 C13 55.0(5) . . . . ? C11 C12 C13 C14 -53.5(5) . . . . ? C12 C13 C14 C15 55.3(5) . . . . ? C1 N C15 C14 179.3(3) . . . . ? C11 N C15 C14 58.1(5) . . . . ? B N C15 C14 -81.9(6) . . . . ? C13 C14 C15 N -60.9(5) . . . . ? N C1 C21 C22 179.9(4) . . . . ? C2 C1 C21 C22 -61.5(5) . . . . ? C1 C21 C22 C23 52.9(5) . . . . ? C21 C22 C23 C24 -52.7(6) . . . . ? C1 C2 C24 C23 -55.5(4) . . . . ? B C2 C24 C23 -160.2(4) . . . . ? C22 C23 C24 C2 52.0(5) . . . . ? C41 B C31 C32 -109.3(5) . . . . ? C2 B C31 C32 110.7(5) . . . . ? N B C31 C32 19.7(7) . . . . ? C41 B C31 C36 69.5(5) . . . . ? C2 B C31 C36 -70.5(4) . . . . ? N B C31 C36 -161.5(4) . . . . ? C36 C31 C32 F32 -176.9(4) . . . . ? B C31 C32 F32 2.0(8) . . . . ? C36 C31 C32 C33 2.0(7) . . . . ? B C31 C32 C33 -179.2(5) . . . . ? F32 C32 C33 F33 -2.0(6) . . . . ? C31 C32 C33 F33 179.1(4) . . . . ? F32 C32 C33 C34 178.0(4) . . . . ? C31 C32 C33 C34 -1.0(7) . . . . ? F33 C33 C34 F34 -0.6(7) . . . . ? C32 C33 C34 F34 179.5(4) . . . . ? F33 C33 C34 C35 179.7(4) . . . . ? C32 C33 C34 C35 -0.2(7) . . . . ? F34 C34 C35 F35 1.6(7) . . . . ? C33 C34 C35 F35 -178.8(4) . . . . ? F34 C34 C35 C36 -179.5(4) . . . . ? C33 C34 C35 C36 0.1(7) . . . . ? F35 C35 C36 F36 0.1(7) . . . . ? C34 C35 C36 F36 -178.8(4) . . . . ? F35 C35 C36 C31 180.0(4) . . . . ? C34 C35 C36 C31 1.1(7) . . . . ? C32 C31 C36 F36 177.8(4) . . . . ? B C31 C36 F36 -1.3(6) . . . . ? C32 C31 C36 C35 -2.1(7) . . . . ? B C31 C36 C35 178.8(4) . . . . ? C31 B C41 C46 51.5(5) . . . . ? C2 B C41 C46 -175.0(4) . . . . ? N B C41 C46 -81.5(4) . . . . ? C31 B C41 C42 -124.4(4) . . . . ? C2 B C41 C42 9.1(6) . . . . ? N B C41 C42 102.7(4) . . . . ? C46 C41 C42 F42 -177.2(4) . . . . ? B C41 C42 F42 -1.1(6) . . . . ? C46 C41 C42 C43 2.7(6) . . . . ? B C41 C42 C43 178.9(4) . . . . ? F42 C42 C43 F43 -0.2(6) . . . . ? C41 C42 C43 F43 179.9(4) . . . . ? F42 C42 C43 C44 177.5(4) . . . . ? C41 C42 C43 C44 -2.5(7) . . . . ? F43 C43 C44 F44 -0.9(7) . . . . ? C42 C43 C44 F44 -178.5(4) . . . . ? F43 C43 C44 C45 178.2(4) . . . . ? C42 C43 C44 C45 0.5(7) . . . . ? C43 C44 C45 F45 -179.2(4) . . . . ? F44 C44 C45 F45 -0.2(7) . . . . ? C43 C44 C45 C46 0.9(7) . . . . ? F44 C44 C45 C46 179.9(4) . . . . ? F45 C45 C46 F46 -0.5(6) . . . . ? C44 C45 C46 F46 179.3(4) . . . . ? F45 C45 C46 C41 179.6(4) . . . . ? C44 C45 C46 C41 -0.5(7) . . . . ? C42 C41 C46 F46 178.9(4) . . . . ? B C41 C46 F46 2.6(6) . . . . ? C42 C41 C46 C45 -1.2(6) . . . . ? B C41 C46 C45 -177.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.775 _diffrn_reflns_theta_full 67.30 _diffrn_measured_fraction_theta_full 0.775 _refine_diff_density_max 0.172 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.041 # Attachment '- 9a.cif' data_erk5280 _database_code_depnum_ccdc_archive 'CCDC 815784' #TrackingRef '- 9a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H34 B F10 N' _chemical_formula_weight 705.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 13.6638(3) _cell_length_b 16.1258(5) _cell_length_c 16.8550(6) _cell_angle_alpha 90.00 _cell_angle_beta 111.633(1) _cell_angle_gamma 90.00 _cell_volume 3452.24(18) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6178 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description pyramide _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 1.000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7535 _exptl_absorpt_correction_T_max 0.7881 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 46576 _diffrn_reflns_av_R_equivalents 0.052 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.93 _diffrn_reflns_theta_max 67.60 _reflns_number_total 6118 _reflns_number_gt 5222 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0828P)^2^+1.6324P] 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 6118 _refine_ls_number_parameters 440 _refine_ls_number_restraints 42 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1589 _refine_ls_wR_factor_gt 0.1508 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.086 _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 N N 0.70132(16) 0.26093(11) 0.29747(11) 0.0505(5) Uani 1 1 d . . . H0 H 0.6591 0.2415 0.2446 0.061 Uiso 1 1 calc R . . B B 0.69360(19) 0.30803(14) 0.11318(15) 0.0422(5) Uani 1 1 d . . . C1 C 0.79630(19) 0.30061(13) 0.28569(14) 0.0493(5) Uani 1 1 d . . . H1 H 0.8406 0.2551 0.2780 0.059 Uiso 1 1 calc R . . C2 C 0.76296(17) 0.35426(12) 0.20454(13) 0.0447(5) Uani 1 1 d . . . H2 H 0.7198 0.4005 0.2125 0.054 Uiso 1 1 calc R . . C3 C 0.58662(17) 0.26563(13) 0.11091(13) 0.0444(5) Uani 1 1 d . . . C4 C 0.50522(17) 0.23222(14) 0.10462(14) 0.0476(5) Uani 1 1 d . . . C5 C 0.41054(17) 0.18700(15) 0.09453(14) 0.0501(5) Uani 1 1 d . . . C6 C 0.4072(2) 0.10199(17) 0.08038(17) 0.0619(6) Uani 1 1 d . . . H6 H 0.4672 0.0745 0.0787 0.074 Uiso 1 1 calc R . . C7 C 0.3164(2) 0.0574(2) 0.0687(2) 0.0823(9) Uani 1 1 d . . . H7 H 0.3147 -0.0001 0.0592 0.099 Uiso 1 1 calc R . . C8 C 0.2288(2) 0.0971(3) 0.0709(2) 0.0919(11) Uani 1 1 d . . . H8 H 0.1670 0.0668 0.0626 0.110 Uiso 1 1 calc R . . C9 C 0.2309(2) 0.1807(3) 0.0853(2) 0.0859(10) Uani 1 1 d . . . H9 H 0.1706 0.2075 0.0869 0.103 Uiso 1 1 calc R . . C10 C 0.3216(2) 0.2263(2) 0.09755(18) 0.0676(7) Uani 1 1 d . . . H10 H 0.3227 0.2836 0.1079 0.081 Uiso 1 1 calc R . . C11 C 0.6339(2) 0.31951(15) 0.32501(16) 0.0614(6) Uani 1 1 d . . . H11A H 0.6736 0.3392 0.3830 0.074 Uiso 1 1 calc R . . H11B H 0.6155 0.3677 0.2869 0.074 Uiso 1 1 calc R . . C12 C 0.5348(3) 0.27695(18) 0.32288(19) 0.0728(8) Uani 1 1 d . . . H12A H 0.4917 0.2626 0.2638 0.087 Uiso 1 1 calc R . . H12B H 0.4941 0.3152 0.3439 0.087 Uiso 1 1 calc R . . C13 C 0.5583(3) 0.19873(19) 0.3769(2) 0.0796(9) Uani 1 1 d . . . H13A H 0.4924 0.1697 0.3692 0.096 Uiso 1 1 calc R . . H13B H 0.5920 0.2135 0.4374 0.096 Uiso 1 1 calc R . . C14 C 0.6308(3) 0.14207(17) 0.3510(2) 0.0776(9) Uani 1 1 d . . . H14A H 0.6497 0.0938 0.3889 0.093 Uiso 1 1 calc R . . H14B H 0.5935 0.1222 0.2926 0.093 Uiso 1 1 calc R . . C15 C 0.7292(2) 0.18668(14) 0.35547(17) 0.0645(7) Uani 1 1 d . . . H15A H 0.7742 0.1491 0.3383 0.077 Uiso 1 1 calc R . . H15B H 0.7684 0.2045 0.4143 0.077 Uiso 1 1 calc R . . C21 C 0.8629(2) 0.34849(16) 0.36591(15) 0.0657(7) Uani 1 1 d . . . H21A H 0.8196 0.3919 0.3773 0.079 Uiso 1 1 calc R . . H21B H 0.8856 0.3106 0.4148 0.079 Uiso 1 1 calc R . . C22 C 0.9590(2) 0.38778(17) 0.35672(17) 0.0718(8) Uani 1 1 d . . . H22A H 0.9969 0.4207 0.4077 0.086 Uiso 1 1 calc R . . H22B H 1.0065 0.3442 0.3519 0.086 Uiso 1 1 calc R . . C23 C 0.9277(2) 0.44275(15) 0.27886(16) 0.0615(6) Uani 1 1 d . . . H23A H 0.9908 0.4651 0.2719 0.074 Uiso 1 1 calc R . . H23B H 0.8854 0.4894 0.2856 0.074 Uiso 1 1 calc R . . C24 C 0.86406(18) 0.39197(14) 0.20045(15) 0.0510(5) Uani 1 1 d . . . H24A H 0.9085 0.3471 0.1934 0.061 Uiso 1 1 calc R . . H24B H 0.8454 0.4276 0.1499 0.061 Uiso 1 1 calc R . . C31 C 0.65051(16) 0.37542(13) 0.03249(13) 0.0442(5) Uani 1 1 d . . . C32 C 0.64450(17) 0.46071(13) 0.03748(14) 0.0478(5) Uani 1 1 d . . . F32 F 0.67784(11) 0.50091(8) 0.11332(8) 0.0606(4) Uani 1 1 d . . . C33 C 0.60338(19) 0.51287(15) -0.03199(17) 0.0579(6) Uani 1 1 d . . . F33 F 0.60307(13) 0.59533(9) -0.02101(11) 0.0791(5) Uani 1 1 d . . . C34 C 0.5611(2) 0.48028(18) -0.11229(16) 0.0662(7) Uani 1 1 d . . . F34 F 0.51982(16) 0.52975(12) -0.18066(11) 0.0967(6) Uani 1 1 d . . . C35 C 0.5623(2) 0.3959(2) -0.12151(16) 0.0700(7) Uani 1 1 d . . . F35 F 0.52044(18) 0.36165(13) -0.19973(10) 0.1059(7) Uani 1 1 d . . . C36 C 0.6065(2) 0.34660(15) -0.05053(15) 0.0567(6) Uani 1 1 d . . . F36 F 0.60576(14) 0.26415(9) -0.06522(9) 0.0788(5) Uani 1 1 d . . . C41 C 0.76866(16) 0.23475(13) 0.09509(13) 0.0428(5) Uani 1 1 d . . . C42 C 0.83480(18) 0.24665(14) 0.04990(14) 0.0491(5) Uani 1 1 d . . . F42 F 0.83855(12) 0.32132(9) 0.01458(9) 0.0654(4) Uani 1 1 d . . . C43 C 0.89890(19) 0.18638(17) 0.03736(16) 0.0585(6) Uani 1 1 d . . . F43 F 0.96020(13) 0.20341(12) -0.00773(12) 0.0843(5) Uani 1 1 d . . . C44 C 0.90146(19) 0.10879(16) 0.07077(17) 0.0590(6) Uani 1 1 d . . . F44 F 0.96445(14) 0.04957(11) 0.05926(13) 0.0883(6) Uani 1 1 d . . . C45 C 0.83903(19) 0.09274(13) 0.11645(15) 0.0518(5) Uani 1 1 d . . . F45 F 0.84021(13) 0.01721(8) 0.15056(11) 0.0720(4) Uani 1 1 d . . . C46 C 0.77617(17) 0.15488(13) 0.12760(14) 0.0444(5) Uani 1 1 d . . . F46 F 0.71979(11) 0.13281(7) 0.17592(9) 0.0564(4) Uani 1 1 d . . . C51 C 1.1173(3) 0.3728(3) 0.1503(4) 0.1457(19) Uani 1 1 d GU . . H51 H 1.0728 0.3267 0.1312 0.175 Uiso 1 1 calc R . . C52 C 1.1048(4) 0.4416(5) 0.0977(3) 0.233(4) Uani 1 1 d GU . . H52 H 1.0518 0.4419 0.0429 0.279 Uiso 1 1 calc R . . C53 C 1.1706(6) 0.5098(3) 0.1260(5) 0.208(3) Uani 1 1 d GU . . H53 H 1.1621 0.5563 0.0905 0.250 Uiso 1 1 calc R . . C54 C 1.2489(5) 0.5094(3) 0.2070(6) 0.243(5) Uani 1 1 d GU . . H54 H 1.2934 0.5556 0.2262 0.291 Uiso 1 1 calc R . . C55 C 1.2615(4) 0.4407(5) 0.2597(3) 0.200(3) Uani 1 1 d GU . . H55 H 1.3145 0.4404 0.3144 0.240 Uiso 1 1 calc R . . C56 C 1.1957(5) 0.3724(3) 0.2313(3) 0.173(3) Uani 1 1 d GU . . C57 C 1.2130(8) 0.3084(6) 0.2879(6) 0.241(4) Uani 1 1 d U . . H57A H 1.2684 0.2731 0.2838 0.362 Uiso 1 1 calc R . . H57B H 1.1489 0.2763 0.2747 0.362 Uiso 1 1 calc R . . H57C H 1.2341 0.3303 0.3454 0.362 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N 0.0777(13) 0.0365(9) 0.0408(9) 0.0020(7) 0.0259(9) 0.0093(9) B 0.0516(13) 0.0340(11) 0.0423(12) 0.0034(9) 0.0187(10) -0.0013(9) C1 0.0639(13) 0.0379(11) 0.0424(11) 0.0022(9) 0.0154(10) 0.0088(10) C2 0.0559(12) 0.0342(10) 0.0408(11) 0.0019(8) 0.0142(9) 0.0053(9) C3 0.0535(12) 0.0396(11) 0.0424(11) 0.0040(9) 0.0203(9) 0.0033(9) C4 0.0530(12) 0.0479(12) 0.0439(11) 0.0076(9) 0.0204(10) 0.0029(10) C5 0.0470(12) 0.0597(14) 0.0429(11) 0.0137(10) 0.0156(9) -0.0010(10) C6 0.0540(13) 0.0638(16) 0.0633(15) 0.0125(12) 0.0161(11) -0.0055(11) C7 0.0715(19) 0.0761(19) 0.090(2) 0.0126(16) 0.0187(16) -0.0222(15) C8 0.0528(16) 0.125(3) 0.089(2) 0.025(2) 0.0161(15) -0.0241(18) C9 0.0515(15) 0.122(3) 0.088(2) 0.024(2) 0.0292(15) 0.0062(17) C10 0.0561(14) 0.0816(19) 0.0673(16) 0.0146(14) 0.0252(12) 0.0070(13) C11 0.0936(18) 0.0435(13) 0.0562(14) 0.0045(10) 0.0384(13) 0.0165(12) C12 0.097(2) 0.0703(17) 0.0679(16) -0.0005(14) 0.0494(16) 0.0153(15) C13 0.116(2) 0.0677(18) 0.0781(19) 0.0021(14) 0.0626(19) 0.0032(16) C14 0.124(3) 0.0487(15) 0.0827(19) 0.0067(13) 0.0645(19) 0.0069(15) C15 0.102(2) 0.0417(13) 0.0603(15) 0.0142(11) 0.0426(14) 0.0179(13) C21 0.0923(19) 0.0508(14) 0.0403(12) 0.0024(10) 0.0084(12) 0.0080(13) C22 0.0751(17) 0.0587(15) 0.0571(15) -0.0002(12) -0.0042(13) 0.0007(13) C23 0.0614(14) 0.0470(13) 0.0613(15) -0.0021(11) 0.0055(12) -0.0019(11) C24 0.0532(12) 0.0416(11) 0.0512(12) 0.0002(10) 0.0109(10) 0.0000(9) C31 0.0452(11) 0.0417(11) 0.0428(11) 0.0039(9) 0.0128(9) -0.0064(9) C32 0.0462(11) 0.0427(12) 0.0493(12) 0.0049(9) 0.0114(9) -0.0020(9) F32 0.0789(9) 0.0376(7) 0.0555(8) 0.0007(6) 0.0134(7) 0.0054(6) C33 0.0538(13) 0.0471(13) 0.0661(15) 0.0161(11) 0.0142(11) 0.0018(10) F33 0.0893(11) 0.0458(8) 0.0886(11) 0.0224(7) 0.0167(9) 0.0089(7) C34 0.0635(15) 0.0683(17) 0.0545(14) 0.0229(12) 0.0072(12) 0.0006(12) F34 0.1027(13) 0.0997(13) 0.0646(10) 0.0406(9) 0.0037(9) 0.0123(10) C35 0.0704(16) 0.0821(19) 0.0410(13) 0.0031(12) 0.0011(11) -0.0111(14) F35 0.1342(16) 0.1081(15) 0.0428(8) 0.0000(9) -0.0055(9) -0.0104(12) C36 0.0654(14) 0.0478(13) 0.0494(13) 0.0005(10) 0.0123(11) -0.0123(11) F36 0.1112(13) 0.0565(9) 0.0515(8) -0.0113(7) 0.0097(8) -0.0194(8) C41 0.0496(11) 0.0387(11) 0.0412(10) -0.0040(8) 0.0182(9) -0.0066(9) C42 0.0552(12) 0.0473(12) 0.0488(12) -0.0017(9) 0.0239(10) -0.0102(10) F42 0.0757(9) 0.0602(9) 0.0716(9) 0.0118(7) 0.0404(8) -0.0111(7) C43 0.0561(13) 0.0700(16) 0.0600(14) -0.0127(12) 0.0337(12) -0.0119(11) F43 0.0819(11) 0.0991(12) 0.0990(12) -0.0078(10) 0.0651(10) -0.0112(9) C44 0.0566(13) 0.0541(14) 0.0721(16) -0.0184(12) 0.0305(12) -0.0009(11) F44 0.0836(11) 0.0731(11) 0.1275(15) -0.0237(10) 0.0616(11) 0.0101(8) C45 0.0601(13) 0.0362(11) 0.0609(14) -0.0070(10) 0.0243(11) -0.0019(9) F45 0.0893(10) 0.0374(7) 0.0961(11) 0.0034(7) 0.0423(9) 0.0079(7) C46 0.0528(12) 0.0395(11) 0.0469(11) -0.0031(9) 0.0253(10) -0.0046(9) F46 0.0786(9) 0.0384(7) 0.0680(8) 0.0085(6) 0.0455(7) 0.0036(6) C51 0.108(3) 0.152(4) 0.174(5) -0.016(4) 0.049(3) 0.010(3) C52 0.228(7) 0.236(8) 0.233(8) -0.016(7) 0.083(6) 0.063(7) C53 0.233(7) 0.192(6) 0.243(8) 0.038(6) 0.139(6) 0.042(6) C54 0.229(8) 0.265(9) 0.276(9) -0.039(7) 0.141(7) -0.006(7) C55 0.181(6) 0.228(7) 0.221(6) -0.121(6) 0.107(5) -0.032(5) C56 0.180(5) 0.226(7) 0.161(5) -0.001(5) 0.118(5) 0.040(5) C57 0.266(8) 0.307(9) 0.223(7) 0.080(6) 0.173(6) 0.061(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 N C15 1.503(3) . ? N C11 1.507(3) . ? N C1 1.524(3) . ? N H0 0.9200 . ? B C3 1.601(3) . ? B C2 1.658(3) . ? B C41 1.665(3) . ? B C31 1.669(3) . ? C1 C21 1.531(3) . ? C1 C2 1.539(3) . ? C1 H1 0.9900 . ? C2 C24 1.534(3) . ? C2 H2 0.9900 . ? C3 C4 1.205(3) . ? C4 C5 1.439(3) . ? C5 C10 1.388(3) . ? C5 C6 1.389(4) . ? C6 C7 1.385(4) . ? C6 H6 0.9400 . ? C7 C8 1.370(5) . ? C7 H7 0.9400 . ? C8 C9 1.368(5) . ? C8 H8 0.9400 . ? C9 C10 1.388(4) . ? C9 H9 0.9400 . ? C10 H10 0.9400 . ? C11 C12 1.507(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C12 C13 1.519(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C13 C14 1.526(4) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C14 C15 1.502(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C21 C22 1.517(4) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C22 C23 1.509(4) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C23 C24 1.525(3) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C31 C32 1.382(3) . ? C31 C36 1.384(3) . ? C32 F32 1.354(3) . ? C32 C33 1.382(3) . ? C33 F33 1.343(3) . ? C33 C34 1.366(4) . ? C34 F34 1.343(3) . ? C34 C35 1.371(4) . ? C35 F35 1.347(3) . ? C35 C36 1.376(4) . ? C36 F36 1.352(3) . ? C41 C46 1.389(3) . ? C41 C42 1.393(3) . ? C42 F42 1.353(3) . ? C42 C43 1.376(3) . ? C43 F43 1.351(3) . ? C43 C44 1.367(4) . ? C44 F44 1.347(3) . ? C44 C45 1.368(3) . ? C45 F45 1.344(3) . ? C45 C46 1.377(3) . ? C46 F46 1.359(2) . ? C51 C52 1.3900 . ? C51 C56 1.3900 . ? C51 H51 0.9400 . ? C52 C53 1.3900 . ? C52 H52 0.9400 . ? C53 C54 1.3900 . ? C53 H53 0.9400 . ? C54 C55 1.3900 . ? C54 H54 0.9400 . ? C55 C56 1.3900 . ? C55 H55 0.9400 . ? C56 C57 1.366(8) . ? C57 H57A 0.9700 . ? C57 H57B 0.9700 . ? C57 H57C 0.9700 . ? 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 C15 N C11 109.65(18) . . ? C15 N C1 113.28(19) . . ? C11 N C1 115.04(17) . . ? C15 N H0 106.0 . . ? C11 N H0 106.0 . . ? C1 N H0 106.0 . . ? C3 B C2 114.73(17) . . ? C3 B C41 108.13(16) . . ? C2 B C41 108.02(17) . . ? C3 B C31 102.35(16) . . ? C2 B C31 111.90(16) . . ? C41 B C31 111.65(17) . . ? N C1 C21 110.71(19) . . ? N C1 C2 111.38(18) . . ? C21 C1 C2 112.72(19) . . ? N C1 H1 107.2 . . ? C21 C1 H1 107.2 . . ? C2 C1 H1 107.2 . . ? C24 C2 C1 106.64(18) . . ? C24 C2 B 110.63(17) . . ? C1 C2 B 116.96(17) . . ? C24 C2 H2 107.4 . . ? C1 C2 H2 107.4 . . ? B C2 H2 107.4 . . ? C4 C3 B 176.3(2) . . ? C3 C4 C5 175.7(2) . . ? C10 C5 C6 118.9(2) . . ? C10 C5 C4 121.7(2) . . ? C6 C5 C4 119.4(2) . . ? C7 C6 C5 120.5(3) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C8 C7 C6 120.0(3) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C9 C8 C7 120.2(3) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 120.5(3) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C5 C10 C9 119.9(3) . . ? C5 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C12 C11 N 110.7(2) . . ? C12 C11 H11A 109.5 . . ? N C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? N C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C11 C12 C13 112.0(3) . . ? C11 C12 H12A 109.2 . . ? C13 C12 H12A 109.2 . . ? C11 C12 H12B 109.2 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C12 C13 C14 109.9(2) . . ? C12 C13 H13A 109.7 . . ? C14 C13 H13A 109.7 . . ? C12 C13 H13B 109.7 . . ? C14 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? C15 C14 C13 111.3(2) . . ? C15 C14 H14A 109.4 . . ? C13 C14 H14A 109.4 . . ? C15 C14 H14B 109.4 . . ? C13 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? C14 C15 N 109.9(2) . . ? C14 C15 H15A 109.7 . . ? N C15 H15A 109.7 . . ? C14 C15 H15B 109.7 . . ? N C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? C22 C21 C1 112.0(2) . . ? C22 C21 H21A 109.2 . . ? C1 C21 H21A 109.2 . . ? C22 C21 H21B 109.2 . . ? C1 C21 H21B 109.2 . . ? H21A C21 H21B 107.9 . . ? C23 C22 C21 110.8(2) . . ? C23 C22 H22A 109.5 . . ? C21 C22 H22A 109.5 . . ? C23 C22 H22B 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 108.1 . . ? C22 C23 C24 109.1(2) . . ? C22 C23 H23A 109.9 . . ? C24 C23 H23A 109.9 . . ? C22 C23 H23B 109.9 . . ? C24 C23 H23B 109.9 . . ? H23A C23 H23B 108.3 . . ? C23 C24 C2 114.1(2) . . ? C23 C24 H24A 108.7 . . ? C2 C24 H24A 108.7 . . ? C23 C24 H24B 108.7 . . ? C2 C24 H24B 108.7 . . ? H24A C24 H24B 107.6 . . ? C32 C31 C36 112.47(19) . . ? C32 C31 B 127.53(19) . . ? C36 C31 B 119.76(19) . . ? F32 C32 C33 113.5(2) . . ? F32 C32 C31 121.81(19) . . ? C33 C32 C31 124.7(2) . . ? F33 C33 C34 119.7(2) . . ? F33 C33 C32 120.5(2) . . ? C34 C33 C32 119.8(2) . . ? F34 C34 C33 120.8(3) . . ? F34 C34 C35 120.8(3) . . ? C33 C34 C35 118.4(2) . . ? F35 C35 C34 119.9(2) . . ? F35 C35 C36 120.4(3) . . ? C34 C35 C36 119.6(2) . . ? F36 C36 C35 115.9(2) . . ? F36 C36 C31 119.1(2) . . ? C35 C36 C31 125.0(2) . . ? C46 C41 C42 112.03(19) . . ? C46 C41 B 123.16(18) . . ? C42 C41 B 124.74(18) . . ? F42 C42 C43 115.58(19) . . ? F42 C42 C41 120.1(2) . . ? C43 C42 C41 124.4(2) . . ? F43 C43 C44 119.4(2) . . ? F43 C43 C42 120.3(2) . . ? C44 C43 C42 120.3(2) . . ? F44 C44 C43 120.7(2) . . ? F44 C44 C45 120.7(2) . . ? C43 C44 C45 118.6(2) . . ? F45 C45 C44 120.0(2) . . ? F45 C45 C46 120.7(2) . . ? C44 C45 C46 119.3(2) . . ? F46 C46 C45 114.28(19) . . ? F46 C46 C41 120.25(18) . . ? C45 C46 C41 125.5(2) . . ? C52 C51 C56 120.0 . . ? C52 C51 H51 120.0 . . ? C56 C51 H51 120.0 . . ? C53 C52 C51 120.0 . . ? C53 C52 H52 120.0 . . ? C51 C52 H52 120.0 . . ? C52 C53 C54 120.0 . . ? C52 C53 H53 120.0 . . ? C54 C53 H53 120.0 . . ? C53 C54 C55 120.0 . . ? C53 C54 H54 120.0 . . ? C55 C54 H54 120.0 . . ? C56 C55 C54 120.0 . . ? C56 C55 H55 120.0 . . ? C54 C55 H55 120.0 . . ? C57 C56 C55 115.8(7) . . ? C57 C56 C51 124.2(7) . . ? C55 C56 C51 120.0 . . ? C56 C57 H57A 109.5 . . ? C56 C57 H57B 109.5 . . ? H57A C57 H57B 109.5 . . ? C56 C57 H57C 109.5 . . ? H57A C57 H57C 109.5 . . ? H57B C57 H57C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N C1 C21 -73.9(2) . . . . ? C11 N C1 C21 53.3(2) . . . . ? C15 N C1 C2 159.82(18) . . . . ? C11 N C1 C2 -72.9(2) . . . . ? N C1 C2 C24 178.92(16) . . . . ? C21 C1 C2 C24 53.8(3) . . . . ? N C1 C2 B -56.7(2) . . . . ? C21 C1 C2 B 178.1(2) . . . . ? C3 B C2 C24 179.42(17) . . . . ? C41 B C2 C24 58.7(2) . . . . ? C31 B C2 C24 -64.5(2) . . . . ? C3 B C2 C1 57.1(3) . . . . ? C41 B C2 C1 -63.6(2) . . . . ? C31 B C2 C1 173.12(18) . . . . ? C2 B C3 C4 -178(100) . . . . ? C41 B C3 C4 -57(3) . . . . ? C31 B C3 C4 61(3) . . . . ? B C3 C4 C5 46(5) . . . . ? C3 C4 C5 C10 -164(3) . . . . ? C3 C4 C5 C6 15(3) . . . . ? C10 C5 C6 C7 0.6(4) . . . . ? C4 C5 C6 C7 -178.6(2) . . . . ? C5 C6 C7 C8 0.1(5) . . . . ? C6 C7 C8 C9 -0.5(5) . . . . ? C7 C8 C9 C10 0.2(5) . . . . ? C6 C5 C10 C9 -0.9(4) . . . . ? C4 C5 C10 C9 178.3(3) . . . . ? C8 C9 C10 C5 0.5(5) . . . . ? C15 N C11 C12 -58.8(3) . . . . ? C1 N C11 C12 172.1(2) . . . . ? N C11 C12 C13 55.9(3) . . . . ? C11 C12 C13 C14 -53.3(3) . . . . ? C12 C13 C14 C15 54.9(4) . . . . ? C13 C14 C15 N -59.1(3) . . . . ? C11 N C15 C14 60.5(3) . . . . ? C1 N C15 C14 -169.52(19) . . . . ? N C1 C21 C22 179.19(19) . . . . ? C2 C1 C21 C22 -55.3(3) . . . . ? C1 C21 C22 C23 55.5(3) . . . . ? C21 C22 C23 C24 -56.3(3) . . . . ? C22 C23 C24 C2 59.8(3) . . . . ? C1 C2 C24 C23 -57.3(2) . . . . ? B C2 C24 C23 174.57(18) . . . . ? C3 B C31 C32 106.6(2) . . . . ? C2 B C31 C32 -16.7(3) . . . . ? C41 B C31 C32 -137.9(2) . . . . ? C3 B C31 C36 -67.4(2) . . . . ? C2 B C31 C36 169.3(2) . . . . ? C41 B C31 C36 48.1(3) . . . . ? C36 C31 C32 F32 176.3(2) . . . . ? B C31 C32 F32 2.0(3) . . . . ? C36 C31 C32 C33 -2.5(3) . . . . ? B C31 C32 C33 -176.8(2) . . . . ? F32 C32 C33 F33 2.7(3) . . . . ? C31 C32 C33 F33 -178.4(2) . . . . ? F32 C32 C33 C34 -176.2(2) . . . . ? C31 C32 C33 C34 2.7(4) . . . . ? F33 C33 C34 F34 0.5(4) . . . . ? C32 C33 C34 F34 179.4(2) . . . . ? F33 C33 C34 C35 -179.8(2) . . . . ? C32 C33 C34 C35 -0.9(4) . . . . ? F34 C34 C35 F35 -0.9(4) . . . . ? C33 C34 C35 F35 179.4(3) . . . . ? F34 C34 C35 C36 179.1(3) . . . . ? C33 C34 C35 C36 -0.6(4) . . . . ? F35 C35 C36 F36 0.8(4) . . . . ? C34 C35 C36 F36 -179.1(3) . . . . ? F35 C35 C36 C31 -179.3(3) . . . . ? C34 C35 C36 C31 0.7(4) . . . . ? C32 C31 C36 F36 -179.4(2) . . . . ? B C31 C36 F36 -4.5(3) . . . . ? C32 C31 C36 C35 0.8(4) . . . . ? B C31 C36 C35 175.6(2) . . . . ? C3 B C41 C46 -38.5(3) . . . . ? C2 B C41 C46 86.2(2) . . . . ? C31 B C41 C46 -150.33(19) . . . . ? C3 B C41 C42 144.9(2) . . . . ? C2 B C41 C42 -90.4(2) . . . . ? C31 B C41 C42 33.0(3) . . . . ? C46 C41 C42 F42 -179.22(19) . . . . ? B C41 C42 F42 -2.3(3) . . . . ? C46 C41 C42 C43 1.1(3) . . . . ? B C41 C42 C43 178.0(2) . . . . ? F42 C42 C43 F43 0.0(3) . . . . ? C41 C42 C43 F43 179.7(2) . . . . ? F42 C42 C43 C44 179.7(2) . . . . ? C41 C42 C43 C44 -0.6(4) . . . . ? F43 C43 C44 F44 0.1(4) . . . . ? C42 C43 C44 F44 -179.6(2) . . . . ? F43 C43 C44 C45 179.8(2) . . . . ? C42 C43 C44 C45 0.1(4) . . . . ? F44 C44 C45 F45 0.1(4) . . . . ? C43 C44 C45 F45 -179.6(2) . . . . ? F44 C44 C45 C46 179.5(2) . . . . ? C43 C44 C45 C46 -0.2(4) . . . . ? F45 C45 C46 F46 1.1(3) . . . . ? C44 C45 C46 F46 -178.2(2) . . . . ? F45 C45 C46 C41 -179.8(2) . . . . ? C44 C45 C46 C41 0.8(4) . . . . ? C42 C41 C46 F46 177.84(19) . . . . ? B C41 C46 F46 0.8(3) . . . . ? C42 C41 C46 C45 -1.2(3) . . . . ? B C41 C46 C45 -178.2(2) . . . . ? C56 C51 C52 C53 0.0 . . . . ? C51 C52 C53 C54 0.0 . . . . ? C52 C53 C54 C55 0.0 . . . . ? C53 C54 C55 C56 0.0 . . . . ? C54 C55 C56 C57 -179.1(5) . . . . ? C54 C55 C56 C51 0.0 . . . . ? C52 C51 C56 C57 179.1(5) . . . . ? C52 C51 C56 C55 0.0 . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 67.60 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.494 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.041 # Attachment '- 9b.cif' data_erk5447 _database_code_depnum_ccdc_archive 'CCDC 815785' #TrackingRef '- 9b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H28 B F10 N' _chemical_formula_weight 579.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.8907(6) _cell_length_b 17.3259(6) _cell_length_c 16.9954(6) _cell_angle_alpha 90.00 _cell_angle_beta 105.094(3) _cell_angle_gamma 90.00 _cell_volume 5370.7(3) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4811 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description column _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2384 _exptl_absorpt_coefficient_mu 1.151 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7239 _exptl_absorpt_correction_T_max 0.8462 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35670 _diffrn_reflns_av_R_equivalents 0.049 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.03 _diffrn_reflns_theta_max 67.72 _reflns_number_total 4766 _reflns_number_gt 4231 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based onall 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^)+(0.0603P)^2^+4.2311P] 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 4766 _refine_ls_number_parameters 373 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1143 _refine_ls_wR_factor_gt 0.1093 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.016 _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 N N 0.20972(7) -0.15460(7) 0.18034(8) 0.0358(3) Uani 1 1 d . . . H0 H 0.1999 -0.1288 0.1314 0.043 Uiso 1 1 calc R . . B B 0.22453(9) 0.02134(10) 0.13871(10) 0.0301(4) Uani 1 1 d . . . C1 C 0.25851(8) -0.10074(9) 0.24272(9) 0.0341(3) Uani 1 1 d . . . H1 H 0.3079 -0.1020 0.2329 0.041 Uiso 1 1 calc R . . C2 C 0.23129(8) -0.01683(9) 0.23034(9) 0.0319(3) Uani 1 1 d . . . H2 H 0.1820 -0.0150 0.2404 0.038 Uiso 1 1 calc R . . C3 C 0.17582(9) -0.02820(9) 0.06456(9) 0.0361(3) Uani 1 1 d . A . C4 C 0.13676(11) -0.05852(11) 0.00569(11) 0.0511(5) Uani 1 1 d D . . C5A C 0.0958(8) -0.0907(4) -0.0742(6) 0.081(3) Uani 0.526(4) 1 d PD A 1 H5AA H 0.0777 -0.1423 -0.0660 0.097 Uiso 0.526(4) 1 calc PR A 1 H5AB H 0.1289 -0.0957 -0.1096 0.097 Uiso 0.526(4) 1 calc PR A 1 C6A C 0.0320(3) -0.0402(4) -0.1152(3) 0.0805(12) Uani 0.526(4) 1 d PD A 1 H6AA H 0.0002 -0.0328 -0.0785 0.097 Uiso 0.526(4) 1 calc PR A 1 H6AB H 0.0032 -0.0659 -0.1645 0.097 Uiso 0.526(4) 1 calc PR A 1 C7A C 0.0577(3) 0.0385(3) -0.1378(3) 0.0842(14) Uani 0.526(4) 1 d PD A 1 H7AA H 0.0840 0.0652 -0.0887 0.126 Uiso 0.526(4) 1 calc PR A 1 H7AB H 0.0156 0.0689 -0.1658 0.126 Uiso 0.526(4) 1 calc PR A 1 H7AC H 0.0900 0.0313 -0.1733 0.126 Uiso 0.526(4) 1 calc PR A 1 C5B C 0.0817(9) -0.0907(5) -0.0655(7) 0.081(3) Uani 0.474(4) 1 d PD A 2 H5BA H 0.0374 -0.1050 -0.0491 0.097 Uiso 0.474(4) 1 calc PR A 2 H5BB H 0.1014 -0.1375 -0.0844 0.097 Uiso 0.474(4) 1 calc PR A 2 C6B C 0.0622(3) -0.0330(4) -0.1343(3) 0.0805(12) Uani 0.474(4) 1 d PD A 2 H6BA H 0.1070 -0.0158 -0.1478 0.097 Uiso 0.474(4) 1 calc PR A 2 H6BB H 0.0307 -0.0579 -0.1827 0.097 Uiso 0.474(4) 1 calc PR A 2 C7B C 0.0232(4) 0.0354(4) -0.1121(4) 0.0842(14) Uani 0.474(4) 1 d PD A 2 H7BA H -0.0230 0.0191 -0.1025 0.126 Uiso 0.474(4) 1 calc PR A 2 H7BB H 0.0139 0.0726 -0.1563 0.126 Uiso 0.474(4) 1 calc PR A 2 H7BC H 0.0534 0.0591 -0.0630 0.126 Uiso 0.474(4) 1 calc PR A 2 C11 C 0.24671(10) -0.22852(9) 0.16725(11) 0.0446(4) Uani 1 1 d . . . H11A H 0.2539 -0.2613 0.2157 0.054 Uiso 1 1 calc R . . H11B H 0.2949 -0.2172 0.1586 0.054 Uiso 1 1 calc R . . C12 C 0.19997(12) -0.27057(11) 0.09375(12) 0.0554(5) Uani 1 1 d . . . H12A H 0.1957 -0.2389 0.0450 0.066 Uiso 1 1 calc R . . H12B H 0.2240 -0.3191 0.0862 0.066 Uiso 1 1 calc R . . C13 C 0.12423(12) -0.28767(11) 0.10351(13) 0.0604(5) Uani 1 1 d . . . H13A H 0.1278 -0.3250 0.1477 0.072 Uiso 1 1 calc R . . H13B H 0.0941 -0.3105 0.0531 0.072 Uiso 1 1 calc R . . C14 C 0.08813(10) -0.21421(11) 0.12269(13) 0.0553(5) Uani 1 1 d . . . H14A H 0.0779 -0.1801 0.0750 0.066 Uiso 1 1 calc R . . H14B H 0.0413 -0.2271 0.1341 0.066 Uiso 1 1 calc R . . C15 C 0.13622(9) -0.17205(10) 0.19527(11) 0.0456(4) Uani 1 1 d . . . H15A H 0.1124 -0.1238 0.2043 0.055 Uiso 1 1 calc R . . H15B H 0.1429 -0.2040 0.2442 0.055 Uiso 1 1 calc R . . C21 C 0.26640(10) -0.13034(10) 0.32922(10) 0.0419(4) Uani 1 1 d . . . H21A H 0.2185 -0.1294 0.3416 0.050 Uiso 1 1 calc R . . H21B H 0.2839 -0.1838 0.3336 0.050 Uiso 1 1 calc R . . C22 C 0.32040(10) -0.08005(11) 0.39016(10) 0.0450(4) Uani 1 1 d . . . H22A H 0.3253 -0.0993 0.4455 0.054 Uiso 1 1 calc R . . H22B H 0.3687 -0.0823 0.3790 0.054 Uiso 1 1 calc R . . C23 C 0.29332(10) 0.00276(10) 0.38371(10) 0.0433(4) Uani 1 1 d . . . H23A H 0.3289 0.0354 0.4216 0.052 Uiso 1 1 calc R . . H23B H 0.2466 0.0055 0.3985 0.052 Uiso 1 1 calc R . . C24 C 0.28313(9) 0.03209(10) 0.29684(9) 0.0380(4) Uani 1 1 d . . . H24A H 0.3313 0.0342 0.2852 0.046 Uiso 1 1 calc R . . H24B H 0.2640 0.0849 0.2936 0.046 Uiso 1 1 calc R . . C31 C 0.30904(8) 0.03113(9) 0.12778(8) 0.0307(3) Uani 1 1 d . . . C32 C 0.35155(9) 0.09722(9) 0.14934(9) 0.0350(3) Uani 1 1 d . . . F32 F 0.32363(5) 0.15992(5) 0.17816(6) 0.0455(2) Uani 1 1 d . . . C33 C 0.42310(9) 0.10430(11) 0.14463(10) 0.0439(4) Uani 1 1 d . . . F33 F 0.46047(6) 0.16999(7) 0.16749(7) 0.0621(3) Uani 1 1 d . . . C34 C 0.45634(9) 0.04342(12) 0.11695(12) 0.0519(5) Uani 1 1 d . . . F34 F 0.52594(6) 0.04923(9) 0.11202(9) 0.0816(4) Uani 1 1 d . . . C35 C 0.41748(10) -0.02353(11) 0.09490(11) 0.0488(4) Uani 1 1 d . . . F35 F 0.44937(7) -0.08403(8) 0.06844(9) 0.0757(4) Uani 1 1 d . . . C36 C 0.34619(9) -0.02804(9) 0.10101(9) 0.0372(4) Uani 1 1 d . . . F36 F 0.31308(6) -0.09723(5) 0.07929(6) 0.0482(3) Uani 1 1 d . . . C41 C 0.17976(8) 0.10533(9) 0.12348(9) 0.0344(3) Uani 1 1 d . . . C42 C 0.17656(9) 0.14569(10) 0.05181(10) 0.0410(4) Uani 1 1 d . . . F42 F 0.21720(6) 0.12164(6) 0.00209(6) 0.0555(3) Uani 1 1 d . . . C43 C 0.13303(11) 0.20887(11) 0.02514(11) 0.0506(5) Uani 1 1 d . . . F43 F 0.13349(8) 0.24307(8) -0.04614(8) 0.0813(4) Uani 1 1 d . . . C44 C 0.08857(10) 0.23650(10) 0.06999(13) 0.0548(5) Uani 1 1 d . . . F44 F 0.04469(7) 0.29733(7) 0.04425(9) 0.0801(4) Uani 1 1 d . . . C45 C 0.09042(10) 0.20151(12) 0.14269(13) 0.0543(5) Uani 1 1 d . . . F45 F 0.04822(8) 0.22781(9) 0.18922(10) 0.0879(5) Uani 1 1 d . . . C46 C 0.13524(9) 0.13764(10) 0.16719(11) 0.0436(4) Uani 1 1 d . . . F46 F 0.13119(7) 0.10675(7) 0.23949(7) 0.0647(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 N 0.0367(7) 0.0307(7) 0.0373(7) 0.0063(5) 0.0048(5) -0.0035(5) B 0.0314(8) 0.0300(8) 0.0276(8) 0.0008(6) 0.0055(7) -0.0014(7) C1 0.0312(7) 0.0353(8) 0.0337(8) 0.0035(6) 0.0047(6) -0.0030(6) C2 0.0300(7) 0.0348(8) 0.0304(8) 0.0023(6) 0.0072(6) -0.0016(6) C3 0.0394(8) 0.0325(8) 0.0344(8) 0.0055(6) 0.0061(7) -0.0033(6) C4 0.0631(12) 0.0444(10) 0.0373(9) 0.0024(8) -0.0021(8) -0.0157(9) C5A 0.108(5) 0.0734(16) 0.043(2) 0.0012(13) -0.014(3) -0.046(2) C6A 0.044(3) 0.149(4) 0.042(2) -0.014(2) -0.0010(16) -0.012(3) C7A 0.070(3) 0.108(3) 0.062(3) -0.002(2) -0.0061(19) 0.030(3) C5B 0.108(5) 0.0734(16) 0.043(2) 0.0012(13) -0.014(3) -0.046(2) C6B 0.044(3) 0.149(4) 0.042(2) -0.014(2) -0.0010(16) -0.012(3) C7B 0.070(3) 0.108(3) 0.062(3) -0.002(2) -0.0061(19) 0.030(3) C11 0.0476(10) 0.0331(9) 0.0520(10) 0.0034(7) 0.0107(8) 0.0006(7) C12 0.0721(13) 0.0363(9) 0.0538(11) -0.0020(8) 0.0096(9) -0.0048(9) C13 0.0668(13) 0.0388(10) 0.0638(12) 0.0031(9) -0.0039(10) -0.0137(9) C14 0.0448(10) 0.0443(10) 0.0681(12) 0.0102(9) -0.0011(9) -0.0130(8) C15 0.0373(9) 0.0410(9) 0.0572(11) 0.0071(8) 0.0100(8) -0.0071(7) C21 0.0445(9) 0.0421(9) 0.0370(9) 0.0122(7) 0.0068(7) 0.0004(7) C22 0.0451(9) 0.0566(11) 0.0307(8) 0.0104(7) 0.0054(7) 0.0021(8) C23 0.0467(9) 0.0522(10) 0.0293(8) 0.0006(7) 0.0068(7) -0.0027(8) C24 0.0420(9) 0.0393(9) 0.0307(8) 0.0007(6) 0.0060(6) -0.0038(7) C31 0.0335(8) 0.0331(8) 0.0244(7) 0.0048(6) 0.0055(6) -0.0003(6) C32 0.0380(8) 0.0355(8) 0.0296(7) 0.0036(6) 0.0054(6) -0.0026(6) F32 0.0524(6) 0.0342(5) 0.0486(5) -0.0064(4) 0.0108(4) -0.0081(4) C33 0.0367(9) 0.0521(10) 0.0375(9) 0.0114(7) 0.0001(7) -0.0126(8) F33 0.0496(6) 0.0650(7) 0.0628(7) 0.0101(5) -0.0012(5) -0.0272(5) C34 0.0304(8) 0.0714(13) 0.0550(11) 0.0136(9) 0.0127(8) 0.0011(8) F34 0.0349(6) 0.1090(11) 0.1056(10) 0.0161(9) 0.0265(6) -0.0015(6) C35 0.0427(9) 0.0570(11) 0.0501(10) 0.0053(8) 0.0184(8) 0.0119(8) F35 0.0636(8) 0.0779(9) 0.0962(10) -0.0053(7) 0.0397(7) 0.0241(6) C36 0.0400(9) 0.0375(8) 0.0339(8) 0.0030(6) 0.0095(7) 0.0014(7) F36 0.0580(6) 0.0348(5) 0.0554(6) -0.0065(4) 0.0215(5) 0.0006(4) C41 0.0309(7) 0.0353(8) 0.0337(8) -0.0012(6) 0.0027(6) -0.0002(6) C42 0.0425(9) 0.0379(9) 0.0399(9) 0.0033(7) 0.0055(7) 0.0028(7) F42 0.0717(7) 0.0586(7) 0.0410(5) 0.0171(5) 0.0234(5) 0.0160(5) C43 0.0531(11) 0.0396(9) 0.0499(10) 0.0089(8) -0.0032(8) 0.0034(8) F43 0.1026(10) 0.0643(8) 0.0676(8) 0.0347(6) 0.0055(7) 0.0198(7) C44 0.0417(10) 0.0362(9) 0.0731(13) -0.0032(9) -0.0089(9) 0.0085(8) F44 0.0627(7) 0.0473(7) 0.1120(11) -0.0004(7) -0.0101(7) 0.0245(6) C45 0.0388(9) 0.0521(11) 0.0703(13) -0.0158(10) 0.0111(9) 0.0086(8) F45 0.0753(9) 0.0884(10) 0.1087(11) -0.0141(8) 0.0396(8) 0.0340(8) C46 0.0393(9) 0.0473(10) 0.0436(9) -0.0020(8) 0.0099(7) 0.0031(7) F46 0.0697(7) 0.0788(8) 0.0560(7) 0.0078(6) 0.0351(6) 0.0228(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 N C11 1.503(2) . ? N C15 1.506(2) . ? N C1 1.5283(19) . ? N H0 0.9200 . ? B C3 1.602(2) . ? B C31 1.663(2) . ? B C2 1.666(2) . ? B C41 1.669(2) . ? C1 C21 1.527(2) . ? C1 C2 1.538(2) . ? C1 H1 0.9900 . ? C2 C24 1.542(2) . ? C2 H2 0.9900 . ? C3 C4 1.199(2) . ? C4 C5B 1.484(6) . ? C4 C5A 1.485(6) . ? C5A C6A 1.505(8) . ? C5A H5AA 0.9800 . ? C5A H5AB 0.9800 . ? C6A C7A 1.530(6) . ? C6A H6AA 0.9800 . ? C6A H6AB 0.9800 . ? C7A H7AA 0.9700 . ? C7A H7AB 0.9700 . ? C7A H7AC 0.9700 . ? C5B C6B 1.509(8) . ? C5B H5BA 0.9800 . ? C5B H5BB 0.9800 . ? C6B C7B 1.495(6) . ? C6B H6BA 0.9800 . ? C6B H6BB 0.9800 . ? C7B H7BA 0.9700 . ? C7B H7BB 0.9700 . ? C7B H7BC 0.9700 . ? C11 C12 1.515(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C12 C13 1.512(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C13 C14 1.519(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C14 C15 1.516(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C21 C22 1.524(2) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C22 C23 1.518(3) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C23 C24 1.525(2) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C31 C36 1.385(2) . ? C31 C32 1.392(2) . ? C32 F32 1.3538(18) . ? C32 C33 1.380(2) . ? C33 F33 1.342(2) . ? C33 C34 1.372(3) . ? C34 F34 1.343(2) . ? C34 C35 1.372(3) . ? C35 F35 1.343(2) . ? C35 C36 1.380(2) . ? C36 F36 1.3581(19) . ? C41 C46 1.378(2) . ? C41 C42 1.392(2) . ? C42 F42 1.347(2) . ? C42 C43 1.373(2) . ? C43 F43 1.351(2) . ? C43 C44 1.360(3) . ? C44 F44 1.342(2) . ? C44 C45 1.369(3) . ? C45 F45 1.340(2) . ? C45 C46 1.390(3) . ? C46 F46 1.361(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 C11 N C15 109.79(12) . . ? C11 N C1 113.79(12) . . ? C15 N C1 114.95(13) . . ? C11 N H0 105.8 . . ? C15 N H0 105.8 . . ? C1 N H0 105.8 . . ? C3 B C31 109.76(12) . . ? C3 B C2 114.27(12) . . ? C31 B C2 107.62(11) . . ? C3 B C41 100.43(12) . . ? C31 B C41 110.86(12) . . ? C2 B C41 113.80(12) . . ? C21 C1 N 110.65(12) . . ? C21 C1 C2 113.23(13) . . ? N C1 C2 111.25(12) . . ? C21 C1 H1 107.1 . . ? N C1 H1 107.1 . . ? C2 C1 H1 107.1 . . ? C1 C2 C24 107.06(12) . . ? C1 C2 B 116.39(12) . . ? C24 C2 B 110.26(12) . . ? C1 C2 H2 107.6 . . ? C24 C2 H2 107.6 . . ? B C2 H2 107.6 . . ? C4 C3 B 173.60(17) . . ? C3 C4 C5B 173.6(7) . . ? C3 C4 C5A 171.3(7) . . ? C5B C4 C5A 13.0(15) . . ? C4 C5A C6A 111.6(7) . . ? C4 C5A H5AA 109.3 . . ? C6A C5A H5AA 109.3 . . ? C4 C5A H5AB 109.3 . . ? C6A C5A H5AB 109.3 . . ? H5AA C5A H5AB 108.0 . . ? C5A C6A C7A 111.5(7) . . ? C5A C6A H6AA 109.3 . . ? C7A C6A H6AA 109.3 . . ? C5A C6A H6AB 109.3 . . ? C7A C6A H6AB 109.3 . . ? H6AA C6A H6AB 108.0 . . ? C4 C5B C6B 111.1(7) . . ? C4 C5B H5BA 109.4 . . ? C6B C5B H5BA 109.4 . . ? C4 C5B H5BB 109.4 . . ? C6B C5B H5BB 109.4 . . ? H5BA C5B H5BB 108.0 . . ? C7B C6B C5B 111.5(8) . . ? C7B C6B H6BA 109.3 . . ? C5B C6B H6BA 109.3 . . ? C7B C6B H6BB 109.3 . . ? C5B C6B H6BB 109.3 . . ? H6BA C6B H6BB 108.0 . . ? C6B C7B H7BA 109.5 . . ? C6B C7B H7BB 109.5 . . ? H7BA C7B H7BB 109.5 . . ? C6B C7B H7BC 109.5 . . ? H7BA C7B H7BC 109.5 . . ? H7BB C7B H7BC 109.5 . . ? N C11 C12 109.77(14) . . ? N C11 H11A 109.7 . . ? C12 C11 H11A 109.7 . . ? N C11 H11B 109.7 . . ? C12 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? C13 C12 C11 111.64(17) . . ? C13 C12 H12A 109.3 . . ? C11 C12 H12A 109.3 . . ? C13 C12 H12B 109.3 . . ? C11 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? C12 C13 C14 110.48(15) . . ? C12 C13 H13A 109.6 . . ? C14 C13 H13A 109.6 . . ? C12 C13 H13B 109.6 . . ? C14 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? C15 C14 C13 111.78(16) . . ? C15 C14 H14A 109.3 . . ? C13 C14 H14A 109.3 . . ? C15 C14 H14B 109.3 . . ? C13 C14 H14B 109.3 . . ? H14A C14 H14B 107.9 . . ? N C15 C14 110.07(15) . . ? N C15 H15A 109.6 . . ? C14 C15 H15A 109.6 . . ? N C15 H15B 109.6 . . ? C14 C15 H15B 109.6 . . ? H15A C15 H15B 108.2 . . ? C22 C21 C1 110.03(13) . . ? C22 C21 H21A 109.7 . . ? C1 C21 H21A 109.7 . . ? C22 C21 H21B 109.7 . . ? C1 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? C23 C22 C21 109.76(14) . . ? C23 C22 H22A 109.7 . . ? C21 C22 H22A 109.7 . . ? C23 C22 H22B 109.7 . . ? C21 C22 H22B 109.7 . . ? H22A C22 H22B 108.2 . . ? C22 C23 C24 109.89(14) . . ? C22 C23 H23A 109.7 . . ? C24 C23 H23A 109.7 . . ? C22 C23 H23B 109.7 . . ? C24 C23 H23B 109.7 . . ? H23A C23 H23B 108.2 . . ? C23 C24 C2 114.97(13) . . ? C23 C24 H24A 108.5 . . ? C2 C24 H24A 108.5 . . ? C23 C24 H24B 108.5 . . ? C2 C24 H24B 108.5 . . ? H24A C24 H24B 107.5 . . ? C36 C31 C32 112.87(14) . . ? C36 C31 B 123.00(13) . . ? C32 C31 B 124.01(13) . . ? F32 C32 C33 115.43(14) . . ? F32 C32 C31 120.20(14) . . ? C33 C32 C31 124.37(15) . . ? F33 C33 C34 119.87(16) . . ? F33 C33 C32 120.52(17) . . ? C34 C33 C32 119.62(16) . . ? F34 C34 C35 120.63(18) . . ? F34 C34 C33 120.44(18) . . ? C35 C34 C33 118.92(16) . . ? F35 C35 C34 119.77(16) . . ? F35 C35 C36 120.83(18) . . ? C34 C35 C36 119.40(17) . . ? F36 C36 C35 114.78(15) . . ? F36 C36 C31 120.39(14) . . ? C35 C36 C31 124.83(16) . . ? C46 C41 C42 111.97(15) . . ? C46 C41 B 128.78(14) . . ? C42 C41 B 118.59(13) . . ? F42 C42 C43 115.45(15) . . ? F42 C42 C41 119.43(14) . . ? C43 C42 C41 125.11(17) . . ? F43 C43 C44 119.84(17) . . ? F43 C43 C42 120.17(18) . . ? C44 C43 C42 119.98(18) . . ? F44 C44 C43 120.9(2) . . ? F44 C44 C45 120.7(2) . . ? C43 C44 C45 118.41(16) . . ? F45 C45 C44 120.17(18) . . ? F45 C45 C46 120.23(19) . . ? C44 C45 C46 119.59(17) . . ? F46 C46 C41 120.86(15) . . ? F46 C46 C45 114.25(16) . . ? C41 C46 C45 124.87(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 C11 N C1 C21 -75.22(17) . . . . ? C15 N C1 C21 52.60(17) . . . . ? C11 N C1 C2 158.00(13) . . . . ? C15 N C1 C2 -74.19(16) . . . . ? C21 C1 C2 C24 53.65(16) . . . . ? N C1 C2 C24 179.01(12) . . . . ? C21 C1 C2 B 177.48(13) . . . . ? N C1 C2 B -57.16(16) . . . . ? C3 B C2 C1 54.14(18) . . . . ? C31 B C2 C1 -68.03(15) . . . . ? C41 B C2 C1 168.72(12) . . . . ? C3 B C2 C24 176.30(13) . . . . ? C31 B C2 C24 54.13(16) . . . . ? C41 B C2 C24 -69.13(16) . . . . ? C31 B C3 C4 -98.5(16) . . . . ? C2 B C3 C4 140.5(16) . . . . ? C41 B C3 C4 18.3(17) . . . . ? B C3 C4 C5B -51(6) . . . . ? B C3 C4 C5A 67(3) . . . . ? C3 C4 C5A C6A -95(3) . . . . ? C5B C4 C5A C6A 60(2) . . . . ? C4 C5A C6A C7A 65.1(13) . . . . ? C3 C4 C5B C6B 74(6) . . . . ? C5A C4 C5B C6B -70(3) . . . . ? C4 C5B C6B C7B -66.2(14) . . . . ? C15 N C11 C12 60.43(18) . . . . ? C1 N C11 C12 -169.14(14) . . . . ? N C11 C12 C13 -58.0(2) . . . . ? C11 C12 C13 C14 54.1(2) . . . . ? C12 C13 C14 C15 -53.4(2) . . . . ? C11 N C15 C14 -59.84(17) . . . . ? C1 N C15 C14 170.36(13) . . . . ? C13 C14 C15 N 56.6(2) . . . . ? N C1 C21 C22 175.09(13) . . . . ? C2 C1 C21 C22 -59.23(18) . . . . ? C1 C21 C22 C23 59.44(19) . . . . ? C21 C22 C23 C24 -57.48(18) . . . . ? C22 C23 C24 C2 56.34(19) . . . . ? C1 C2 C24 C23 -52.76(18) . . . . ? B C2 C24 C23 179.73(14) . . . . ? C3 B C31 C36 -40.21(18) . . . . ? C2 B C31 C36 84.71(16) . . . . ? C41 B C31 C36 -150.25(13) . . . . ? C3 B C31 C32 144.16(14) . . . . ? C2 B C31 C32 -90.91(16) . . . . ? C41 B C31 C32 34.12(18) . . . . ? C36 C31 C32 F32 -178.83(12) . . . . ? B C31 C32 F32 -2.8(2) . . . . ? C36 C31 C32 C33 0.3(2) . . . . ? B C31 C32 C33 176.30(14) . . . . ? F32 C32 C33 F33 -0.2(2) . . . . ? C31 C32 C33 F33 -179.32(14) . . . . ? F32 C32 C33 C34 179.31(15) . . . . ? C31 C32 C33 C34 0.2(2) . . . . ? F33 C33 C34 F34 -0.5(3) . . . . ? C32 C33 C34 F34 -179.94(15) . . . . ? F33 C33 C34 C35 179.17(15) . . . . ? C32 C33 C34 C35 -0.3(3) . . . . ? F34 C34 C35 F35 0.3(3) . . . . ? C33 C34 C35 F35 -179.32(16) . . . . ? F34 C34 C35 C36 179.64(16) . . . . ? C33 C34 C35 C36 0.0(3) . . . . ? F35 C35 C36 F36 0.6(2) . . . . ? C34 C35 C36 F36 -178.71(15) . . . . ? F35 C35 C36 C31 179.82(15) . . . . ? C34 C35 C36 C31 0.5(3) . . . . ? C32 C31 C36 F36 178.54(13) . . . . ? B C31 C36 F36 2.5(2) . . . . ? C32 C31 C36 C35 -0.6(2) . . . . ? B C31 C36 C35 -176.67(15) . . . . ? C3 B C41 C46 106.84(18) . . . . ? C31 B C41 C46 -137.18(16) . . . . ? C2 B C41 C46 -15.7(2) . . . . ? C3 B C41 C42 -63.08(17) . . . . ? C31 B C41 C42 52.90(18) . . . . ? C2 B C41 C42 174.37(13) . . . . ? C46 C41 C42 F42 179.79(15) . . . . ? B C41 C42 F42 -8.7(2) . . . . ? C46 C41 C42 C43 -1.9(2) . . . . ? B C41 C42 C43 169.65(16) . . . . ? F42 C42 C43 F43 -0.7(3) . . . . ? C41 C42 C43 F43 -179.08(16) . . . . ? F42 C42 C43 C44 178.39(16) . . . . ? C41 C42 C43 C44 0.0(3) . . . . ? F43 C43 C44 F44 0.3(3) . . . . ? C42 C43 C44 F44 -178.83(16) . . . . ? F43 C43 C44 C45 -178.76(17) . . . . ? C42 C43 C44 C45 2.1(3) . . . . ? F44 C44 C45 F45 0.0(3) . . . . ? C43 C44 C45 F45 178.99(18) . . . . ? F44 C44 C45 C46 178.71(17) . . . . ? C43 C44 C45 C46 -2.3(3) . . . . ? C42 C41 C46 F46 -179.55(15) . . . . ? B C41 C46 F46 10.0(3) . . . . ? C42 C41 C46 C45 1.8(3) . . . . ? B C41 C46 C45 -168.71(16) . . . . ? F45 C45 C46 F46 0.2(3) . . . . ? C44 C45 C46 F46 -178.54(17) . . . . ? F45 C45 C46 C41 178.98(17) . . . . ? C44 C45 C46 C41 0.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 67.72 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.296 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.039 # Attachment '- 10.cif' data_erk5712 _database_code_depnum_ccdc_archive 'CCDC 815786' #TrackingRef '- 10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H24 B F10 N' _chemical_formula_weight 635.34 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 P21/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 8.9726(4) _cell_length_b 13.4786(6) _cell_length_c 24.6543(17) _cell_angle_alpha 90.00 _cell_angle_beta 93.952(4) _cell_angle_gamma 90.00 _cell_volume 2974.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4923 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 1.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7338 _exptl_absorpt_correction_T_max 0.9471 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23259 _diffrn_reflns_av_R_equivalents 0.063 _diffrn_reflns_av_sigmaI/netI 0.0463 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.74 _diffrn_reflns_theta_max 67.37 _reflns_number_total 5010 _reflns_number_gt 3379 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0563P)^2^+1.6154P] 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 5010 _refine_ls_number_parameters 406 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0855 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1557 _refine_ls_wR_factor_gt 0.1222 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _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 N N 0.7050(3) 0.72299(16) 0.15360(9) 0.0421(5) Uani 1 1 d . . . H0 H 0.7878 0.7109 0.1346 0.051 Uiso 1 1 calc R . . B B 0.8851(4) 0.5173(2) 0.14138(13) 0.0434(8) Uani 1 1 d . . . C1 C 0.6485(3) 0.6207(2) 0.17084(12) 0.0438(7) Uani 1 1 d . . . H1 H 0.6023 0.5889 0.1376 0.053 Uiso 1 1 calc R . . C2 C 0.7833(3) 0.5565(2) 0.19013(11) 0.0437(7) Uani 1 1 d . . . H2A H 0.7471 0.4987 0.2094 0.052 Uiso 1 1 calc R . . H2B H 0.8474 0.5950 0.2162 0.052 Uiso 1 1 calc R . . C3 C 0.9477(3) 0.6097(2) 0.10957(12) 0.0494(7) Uani 1 1 d . . . C4 C 1.0041(4) 0.6798(3) 0.08772(13) 0.0545(8) Uani 1 1 d . . . C5 C 1.0645(4) 0.7628(2) 0.05953(13) 0.0552(8) Uani 1 1 d . . . C6 C 1.1635(4) 0.8288(3) 0.08708(16) 0.0701(10) Uani 1 1 d . . . H6 H 1.1942 0.8171 0.1237 0.084 Uiso 1 1 calc R . . C7 C 1.2164(5) 0.9106(3) 0.0611(2) 0.0942(14) Uani 1 1 d . . . H7 H 1.2813 0.9553 0.0802 0.113 Uiso 1 1 calc R . . C8 C 1.1742(6) 0.9266(4) 0.0079(3) 0.1063(17) Uani 1 1 d . . . H8 H 1.2117 0.9819 -0.0100 0.128 Uiso 1 1 calc R . . C9 C 1.0779(6) 0.8631(4) -0.0202(2) 0.1023(16) Uani 1 1 d . . . H9 H 1.0487 0.8756 -0.0569 0.123 Uiso 1 1 calc R . . C10 C 1.0233(5) 0.7801(3) 0.00561(15) 0.0760(11) Uani 1 1 d . . . H10 H 0.9584 0.7360 -0.0138 0.091 Uiso 1 1 calc R . . C11 C 0.7560(3) 0.7906(2) 0.19938(12) 0.0492(7) Uani 1 1 d . . . H11A H 0.8264 0.7553 0.2247 0.059 Uiso 1 1 calc R . . H11B H 0.6701 0.8109 0.2192 0.059 Uiso 1 1 calc R . . C12 C 0.8310(4) 0.8814(2) 0.17756(14) 0.0577(8) Uani 1 1 d . . . H12A H 0.9208 0.8611 0.1600 0.069 Uiso 1 1 calc R . . H12B H 0.8620 0.9256 0.2078 0.069 Uiso 1 1 calc R . . C13 C 0.7275(4) 0.9371(2) 0.13694(14) 0.0620(9) Uani 1 1 d . . . H13A H 0.6440 0.9652 0.1555 0.074 Uiso 1 1 calc R . . H13B H 0.7819 0.9919 0.1212 0.074 Uiso 1 1 calc R . . C14 C 0.6681(4) 0.8676(2) 0.09220(14) 0.0615(9) Uani 1 1 d . . . H14A H 0.5943 0.9028 0.0681 0.074 Uiso 1 1 calc R . . H14B H 0.7503 0.8472 0.0705 0.074 Uiso 1 1 calc R . . C15 C 0.5962(4) 0.7763(2) 0.11510(14) 0.0600(9) Uani 1 1 d . . . H15A H 0.5086 0.7961 0.1342 0.072 Uiso 1 1 calc R . . H15B H 0.5626 0.7318 0.0853 0.072 Uiso 1 1 calc R . . C21 C 0.5264(3) 0.6313(2) 0.21002(12) 0.0453(7) Uani 1 1 d . . . C22 C 0.3777(3) 0.6380(2) 0.18986(14) 0.0525(8) Uani 1 1 d . . . H22 H 0.3544 0.6370 0.1521 0.063 Uiso 1 1 calc R . . C23 C 0.2642(4) 0.6462(2) 0.22471(17) 0.0643(10) Uani 1 1 d . . . H23 H 0.1646 0.6519 0.2106 0.077 Uiso 1 1 calc R . . C24 C 0.2967(4) 0.6461(2) 0.28005(17) 0.0672(10) Uani 1 1 d . . . H24 H 0.2194 0.6506 0.3038 0.081 Uiso 1 1 calc R . . C25 C 0.4432(4) 0.6395(2) 0.30050(15) 0.0645(9) Uani 1 1 d . . . H25 H 0.4658 0.6398 0.3383 0.077 Uiso 1 1 calc R . . C26 C 0.5574(4) 0.6323(2) 0.26562(13) 0.0523(8) Uani 1 1 d . . . H26 H 0.6570 0.6280 0.2800 0.063 Uiso 1 1 calc R . . C31 C 1.0374(3) 0.4570(2) 0.16368(12) 0.0450(7) Uani 1 1 d . . . C32 C 1.1338(3) 0.4234(2) 0.12586(13) 0.0540(8) Uani 1 1 d . . . F32 F 1.0947(2) 0.43323(17) 0.07240(8) 0.0724(6) Uani 1 1 d . . . C33 C 1.2703(4) 0.3803(3) 0.13876(16) 0.0676(10) Uani 1 1 d . . . F33 F 1.3558(2) 0.3488(2) 0.09950(11) 0.1092(9) Uani 1 1 d . . . C34 C 1.3179(4) 0.3689(3) 0.19220(17) 0.0660(10) Uani 1 1 d . . . F34 F 1.4538(2) 0.32798(19) 0.20573(10) 0.0942(7) Uani 1 1 d . . . C35 C 1.2295(4) 0.3980(2) 0.23111(14) 0.0557(8) Uani 1 1 d . . . F35 F 1.2738(2) 0.38745(16) 0.28429(9) 0.0814(6) Uani 1 1 d . . . C36 C 1.0915(3) 0.4398(2) 0.21658(13) 0.0495(7) Uani 1 1 d . . . F36 F 1.0098(2) 0.46638(15) 0.25873(7) 0.0643(5) Uani 1 1 d . . . C41 C 0.7826(3) 0.4419(2) 0.10186(11) 0.0419(7) Uani 1 1 d . . . C42 C 0.7254(3) 0.4603(2) 0.04913(12) 0.0493(7) Uani 1 1 d . . . F42 F 0.7436(2) 0.54998(15) 0.02609(7) 0.0686(5) Uani 1 1 d . . . C43 C 0.6457(3) 0.3915(3) 0.01732(12) 0.0556(8) Uani 1 1 d . . . F43 F 0.5946(2) 0.41464(17) -0.03401(7) 0.0788(6) Uani 1 1 d . . . C44 C 0.6169(3) 0.3002(3) 0.03821(13) 0.0573(8) Uani 1 1 d . . . F44 F 0.5354(2) 0.23292(16) 0.00829(9) 0.0827(6) Uani 1 1 d . . . C45 C 0.6682(3) 0.2779(2) 0.09020(13) 0.0533(8) Uani 1 1 d . . . F45 F 0.6381(2) 0.18878(14) 0.11149(9) 0.0762(6) Uani 1 1 d . . . C46 C 0.7476(3) 0.3482(2) 0.12026(12) 0.0457(7) Uani 1 1 d . . . F46 F 0.79315(19) 0.32150(13) 0.17195(7) 0.0576(5) 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 N 0.0485(13) 0.0374(12) 0.0403(13) 0.0006(10) 0.0022(10) 0.0016(10) B 0.0451(18) 0.0436(18) 0.0412(19) 0.0016(15) 0.0004(15) 0.0039(15) C1 0.0501(16) 0.0356(15) 0.0455(16) -0.0009(13) 0.0024(13) 0.0003(12) C2 0.0511(16) 0.0376(15) 0.0422(16) -0.0014(13) 0.0015(13) 0.0030(13) C3 0.0552(18) 0.0489(18) 0.0443(17) 0.0043(15) 0.0042(14) 0.0020(15) C4 0.0575(19) 0.0565(19) 0.0501(18) 0.0017(16) 0.0086(15) 0.0063(16) C5 0.063(2) 0.0506(18) 0.054(2) 0.0087(16) 0.0198(16) 0.0060(16) C6 0.065(2) 0.068(2) 0.079(3) 0.006(2) 0.0131(19) -0.0050(19) C7 0.085(3) 0.071(3) 0.131(4) 0.010(3) 0.037(3) -0.013(2) C8 0.128(4) 0.073(3) 0.125(5) 0.035(3) 0.056(4) 0.010(3) C9 0.143(4) 0.095(4) 0.073(3) 0.033(3) 0.035(3) 0.017(3) C10 0.101(3) 0.074(2) 0.056(2) 0.010(2) 0.019(2) 0.009(2) C11 0.0614(18) 0.0440(17) 0.0412(16) -0.0056(13) -0.0032(14) -0.0011(14) C12 0.070(2) 0.0464(18) 0.057(2) -0.0021(16) 0.0041(16) -0.0083(16) C13 0.077(2) 0.0434(18) 0.067(2) 0.0067(16) 0.0161(18) 0.0016(16) C14 0.074(2) 0.0540(19) 0.056(2) 0.0141(17) 0.0001(17) 0.0043(17) C15 0.065(2) 0.0541(19) 0.058(2) 0.0133(16) -0.0166(16) -0.0016(16) C21 0.0497(17) 0.0353(15) 0.0511(18) -0.0024(13) 0.0052(14) -0.0025(13) C22 0.0486(18) 0.0423(16) 0.066(2) -0.0021(15) 0.0017(15) -0.0024(14) C23 0.0473(18) 0.0482(19) 0.098(3) -0.0018(19) 0.0113(19) -0.0067(15) C24 0.063(2) 0.0475(19) 0.094(3) -0.004(2) 0.030(2) -0.0019(16) C25 0.079(2) 0.057(2) 0.059(2) -0.0015(17) 0.0180(18) 0.0010(18) C26 0.0553(18) 0.0490(18) 0.0533(19) 0.0004(15) 0.0096(15) 0.0001(14) C31 0.0499(16) 0.0414(16) 0.0435(17) 0.0032(13) 0.0019(13) -0.0048(13) C32 0.0443(17) 0.066(2) 0.0514(19) -0.0016(16) 0.0036(14) 0.0056(15) F32 0.0644(11) 0.1019(16) 0.0519(12) -0.0048(11) 0.0102(9) 0.0187(11) C33 0.051(2) 0.075(2) 0.078(3) 0.001(2) 0.0126(18) 0.0105(18) F33 0.0683(14) 0.156(2) 0.1060(19) 0.0013(17) 0.0258(13) 0.0440(15) C34 0.0435(18) 0.061(2) 0.092(3) 0.012(2) -0.0026(19) 0.0059(16) F34 0.0505(11) 0.1017(17) 0.128(2) 0.0151(15) -0.0123(12) 0.0185(11) C35 0.0530(18) 0.0502(18) 0.061(2) 0.0100(16) -0.0162(16) -0.0032(15) F35 0.0846(14) 0.0822(14) 0.0728(14) 0.0177(11) -0.0282(11) 0.0043(11) C36 0.0537(18) 0.0439(17) 0.0507(19) 0.0033(14) 0.0028(15) -0.0025(14) F36 0.0723(12) 0.0764(13) 0.0440(10) 0.0080(9) 0.0017(9) 0.0076(10) C41 0.0414(15) 0.0467(16) 0.0377(15) 0.0005(13) 0.0036(12) 0.0084(13) C42 0.0503(17) 0.0524(18) 0.0454(18) 0.0063(15) 0.0053(14) 0.0054(14) F42 0.0779(13) 0.0723(13) 0.0537(11) 0.0195(10) -0.0085(9) -0.0053(10) C43 0.0554(18) 0.072(2) 0.0384(17) -0.0030(16) -0.0045(14) 0.0092(16) F43 0.0845(14) 0.1036(16) 0.0457(11) 0.0005(11) -0.0153(10) -0.0013(12) C44 0.0531(18) 0.061(2) 0.056(2) -0.0164(17) -0.0054(15) 0.0027(16) F44 0.0877(14) 0.0774(14) 0.0794(14) -0.0243(12) -0.0198(11) -0.0089(11) C45 0.0562(18) 0.0436(17) 0.060(2) 0.0014(16) -0.0003(15) 0.0026(15) F45 0.0857(14) 0.0512(11) 0.0894(15) 0.0036(10) -0.0107(11) -0.0116(10) C46 0.0472(16) 0.0486(17) 0.0408(16) 0.0023(14) -0.0006(13) 0.0052(13) F46 0.0681(11) 0.0529(10) 0.0501(10) 0.0107(8) -0.0081(8) -0.0046(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 N C15 1.498(4) . ? N C11 1.497(3) . ? N C1 1.538(3) . ? N H0 0.9200 . ? B C3 1.594(5) . ? B C41 1.644(4) . ? B C2 1.646(4) . ? B C31 1.652(4) . ? C1 C21 1.516(4) . ? C1 C2 1.536(4) . ? C1 H1 0.9900 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 C4 1.216(4) . ? C4 C5 1.442(5) . ? C5 C10 1.375(5) . ? C5 C6 1.399(5) . ? C6 C7 1.376(5) . ? C6 H6 0.9400 . ? C7 C8 1.359(7) . ? C7 H7 0.9400 . ? C8 C9 1.369(7) . ? C8 H8 0.9400 . ? C9 C10 1.393(6) . ? C9 H9 0.9400 . ? C10 H10 0.9400 . ? C11 C12 1.514(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C12 C13 1.517(5) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C13 C14 1.516(5) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C14 C15 1.516(5) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C21 C26 1.380(4) . ? C21 C22 1.395(4) . ? C22 C23 1.381(5) . ? C22 H22 0.9400 . ? C23 C24 1.375(5) . ? C23 H23 0.9400 . ? C24 C25 1.378(5) . ? C24 H24 0.9400 . ? C25 C26 1.386(5) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? C31 C36 1.379(4) . ? C31 C32 1.391(4) . ? C32 F32 1.347(4) . ? C32 C33 1.373(4) . ? C33 F33 1.344(4) . ? C33 C34 1.365(5) . ? C34 C35 1.345(5) . ? C34 F34 1.358(4) . ? C35 F35 1.351(4) . ? C35 C36 1.385(4) . ? C36 F36 1.360(3) . ? C41 C46 1.386(4) . ? C41 C42 1.387(4) . ? C42 F42 1.350(3) . ? C42 C43 1.382(4) . ? C43 F43 1.352(3) . ? C43 C44 1.366(5) . ? C44 F44 1.352(3) . ? C44 C45 1.365(4) . ? C45 F45 1.346(4) . ? C45 C46 1.372(4) . ? C46 F46 1.360(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 C15 N C11 109.7(2) . . ? C15 N C1 113.1(2) . . ? C11 N C1 115.2(2) . . ? C15 N H0 106.0 . . ? C11 N H0 106.0 . . ? C1 N H0 106.0 . . ? C3 B C41 113.1(2) . . ? C3 B C2 109.9(2) . . ? C41 B C2 108.4(2) . . ? C3 B C31 103.7(2) . . ? C41 B C31 108.0(2) . . ? C2 B C31 113.8(2) . . ? C21 C1 C2 116.3(2) . . ? C21 C1 N 111.0(2) . . ? C2 C1 N 108.9(2) . . ? C21 C1 H1 106.7 . . ? C2 C1 H1 106.7 . . ? N C1 H1 106.7 . . ? C1 C2 B 114.8(2) . . ? C1 C2 H2A 108.6 . . ? B C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? B C2 H2B 108.6 . . ? H2A C2 H2B 107.5 . . ? C4 C3 B 175.6(3) . . ? C3 C4 C5 176.9(4) . . ? C10 C5 C6 118.7(3) . . ? C10 C5 C4 120.8(3) . . ? C6 C5 C4 120.4(3) . . ? C7 C6 C5 120.8(4) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C8 C7 C6 119.6(5) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 120.9(4) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C8 C9 C10 120.0(5) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C5 C10 C9 119.9(4) . . ? C5 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? N C11 C12 110.1(2) . . ? N C11 H11A 109.6 . . ? C12 C11 H11A 109.6 . . ? N C11 H11B 109.6 . . ? C12 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? C11 C12 C13 111.6(3) . . ? C11 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? C11 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? C14 C13 C12 110.1(3) . . ? C14 C13 H13A 109.6 . . ? C12 C13 H13A 109.6 . . ? C14 C13 H13B 109.6 . . ? C12 C13 H13B 109.6 . . ? H13A C13 H13B 108.2 . . ? C15 C14 C13 111.6(3) . . ? C15 C14 H14A 109.3 . . ? C13 C14 H14A 109.3 . . ? C15 C14 H14B 109.3 . . ? C13 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? N C15 C14 110.5(3) . . ? N C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? N C15 H15B 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C26 C21 C22 118.4(3) . . ? C26 C21 C1 121.9(3) . . ? C22 C21 C1 119.6(3) . . ? C23 C22 C21 120.8(3) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C24 C23 C22 120.1(3) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C23 C24 C25 119.7(3) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C24 C25 C26 120.3(3) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C21 C26 C25 120.7(3) . . ? C21 C26 H26 119.7 . . ? C25 C26 H26 119.7 . . ? C36 C31 C32 112.6(3) . . ? C36 C31 B 128.8(3) . . ? C32 C31 B 118.4(3) . . ? F32 C32 C33 115.9(3) . . ? F32 C32 C31 119.5(3) . . ? C33 C32 C31 124.6(3) . . ? F33 C33 C34 120.2(3) . . ? F33 C33 C32 120.7(3) . . ? C34 C33 C32 119.1(3) . . ? C35 C34 F34 120.5(3) . . ? C35 C34 C33 119.7(3) . . ? F34 C34 C33 119.9(3) . . ? C34 C35 F35 120.8(3) . . ? C34 C35 C36 119.7(3) . . ? F35 C35 C36 119.5(3) . . ? F36 C36 C31 120.4(3) . . ? F36 C36 C35 115.4(3) . . ? C31 C36 C35 124.2(3) . . ? C46 C41 C42 113.1(3) . . ? C46 C41 B 120.0(2) . . ? C42 C41 B 126.9(3) . . ? F42 C42 C43 115.8(3) . . ? F42 C42 C41 120.5(3) . . ? C43 C42 C41 123.7(3) . . ? F43 C43 C44 120.0(3) . . ? F43 C43 C42 120.3(3) . . ? C44 C43 C42 119.7(3) . . ? F44 C44 C45 120.0(3) . . ? F44 C44 C43 120.5(3) . . ? C45 C44 C43 119.5(3) . . ? F45 C45 C44 119.9(3) . . ? F45 C45 C46 121.1(3) . . ? C44 C45 C46 119.0(3) . . ? F46 C46 C45 115.8(3) . . ? F46 C46 C41 119.2(3) . . ? C45 C46 C41 125.0(3) . . ? 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 C15 N C1 C21 -73.1(3) . . . . ? C11 N C1 C21 54.3(3) . . . . ? C15 N C1 C2 157.6(2) . . . . ? C11 N C1 C2 -75.0(3) . . . . ? C21 C1 C2 B 161.3(2) . . . . ? N C1 C2 B -72.4(3) . . . . ? C3 B C2 C1 59.1(3) . . . . ? C41 B C2 C1 -65.0(3) . . . . ? C31 B C2 C1 174.8(2) . . . . ? C41 B C3 C4 -146(4) . . . . ? C2 B C3 C4 92(4) . . . . ? C31 B C3 C4 -30(4) . . . . ? B C3 C4 C5 171(5) . . . . ? C3 C4 C5 C10 -19(7) . . . . ? C3 C4 C5 C6 159(6) . . . . ? C10 C5 C6 C7 1.3(5) . . . . ? C4 C5 C6 C7 -177.0(3) . . . . ? C5 C6 C7 C8 -1.2(6) . . . . ? C6 C7 C8 C9 1.0(7) . . . . ? C7 C8 C9 C10 -0.9(8) . . . . ? C6 C5 C10 C9 -1.1(6) . . . . ? C4 C5 C10 C9 177.2(4) . . . . ? C8 C9 C10 C5 0.9(7) . . . . ? C15 N C11 C12 -59.9(3) . . . . ? C1 N C11 C12 171.1(2) . . . . ? N C11 C12 C13 57.8(3) . . . . ? C11 C12 C13 C14 -54.3(4) . . . . ? C12 C13 C14 C15 53.7(4) . . . . ? C11 N C15 C14 59.5(3) . . . . ? C1 N C15 C14 -170.3(3) . . . . ? C13 C14 C15 N -57.0(4) . . . . ? C2 C1 C21 C26 33.1(4) . . . . ? N C1 C21 C26 -92.1(3) . . . . ? C2 C1 C21 C22 -145.5(3) . . . . ? N C1 C21 C22 89.3(3) . . . . ? C26 C21 C22 C23 0.4(4) . . . . ? C1 C21 C22 C23 179.1(3) . . . . ? C21 C22 C23 C24 -1.1(5) . . . . ? C22 C23 C24 C25 1.0(5) . . . . ? C23 C24 C25 C26 -0.4(5) . . . . ? C22 C21 C26 C25 0.3(4) . . . . ? C1 C21 C26 C25 -178.3(3) . . . . ? C24 C25 C26 C21 -0.3(5) . . . . ? C3 B C31 C36 116.3(3) . . . . ? C41 B C31 C36 -123.4(3) . . . . ? C2 B C31 C36 -3.1(4) . . . . ? C3 B C31 C32 -58.7(3) . . . . ? C41 B C31 C32 61.6(3) . . . . ? C2 B C31 C32 -178.0(3) . . . . ? C36 C31 C32 F32 178.7(3) . . . . ? B C31 C32 F32 -5.6(4) . . . . ? C36 C31 C32 C33 -1.8(5) . . . . ? B C31 C32 C33 173.9(3) . . . . ? F32 C32 C33 F33 -1.2(5) . . . . ? C31 C32 C33 F33 179.3(3) . . . . ? F32 C32 C33 C34 179.3(3) . . . . ? C31 C32 C33 C34 -0.3(6) . . . . ? F33 C33 C34 C35 -178.1(3) . . . . ? C32 C33 C34 C35 1.5(6) . . . . ? F33 C33 C34 F34 1.6(6) . . . . ? C32 C33 C34 F34 -178.9(3) . . . . ? F34 C34 C35 F35 0.2(5) . . . . ? C33 C34 C35 F35 179.8(3) . . . . ? F34 C34 C35 C36 179.9(3) . . . . ? C33 C34 C35 C36 -0.4(5) . . . . ? C32 C31 C36 F36 -178.8(3) . . . . ? B C31 C36 F36 6.0(5) . . . . ? C32 C31 C36 C35 2.9(4) . . . . ? B C31 C36 C35 -172.3(3) . . . . ? C34 C35 C36 F36 179.7(3) . . . . ? F35 C35 C36 F36 -0.6(4) . . . . ? C34 C35 C36 C31 -2.0(5) . . . . ? F35 C35 C36 C31 177.8(3) . . . . ? C3 B C41 C46 165.8(3) . . . . ? C2 B C41 C46 -72.0(3) . . . . ? C31 B C41 C46 51.7(3) . . . . ? C3 B C41 C42 -13.0(4) . . . . ? C2 B C41 C42 109.2(3) . . . . ? C31 B C41 C42 -127.1(3) . . . . ? C46 C41 C42 F42 176.9(3) . . . . ? B C41 C42 F42 -4.2(4) . . . . ? C46 C41 C42 C43 -2.0(4) . . . . ? B C41 C42 C43 176.8(3) . . . . ? F42 C42 C43 F43 1.6(4) . . . . ? C41 C42 C43 F43 -179.4(3) . . . . ? F42 C42 C43 C44 -177.4(3) . . . . ? C41 C42 C43 C44 1.6(5) . . . . ? F43 C43 C44 F44 -1.1(5) . . . . ? C42 C43 C44 F44 178.0(3) . . . . ? F43 C43 C44 C45 -179.5(3) . . . . ? C42 C43 C44 C45 -0.4(5) . . . . ? F44 C44 C45 F45 0.4(5) . . . . ? C43 C44 C45 F45 178.8(3) . . . . ? F44 C44 C45 C46 -178.5(3) . . . . ? C43 C44 C45 C46 0.0(5) . . . . ? F45 C45 C46 F46 0.2(4) . . . . ? C44 C45 C46 F46 179.0(3) . . . . ? F45 C45 C46 C41 -179.5(3) . . . . ? C44 C45 C46 C41 -0.6(5) . . . . ? C42 C41 C46 F46 -178.0(2) . . . . ? B C41 C46 F46 3.0(4) . . . . ? C42 C41 C46 C45 1.6(4) . . . . ? B C41 C46 C45 -177.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.937 _diffrn_reflns_theta_full 67.37 _diffrn_measured_fraction_theta_full 0.937 _refine_diff_density_max 0.348 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.112 # Attachment '- 11b.cif' data_erk5709 _database_code_depnum_ccdc_archive 'CCDC 815787' #TrackingRef '- 11b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H20 B F10 N' _chemical_formula_weight 535.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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 orthorhombic _symmetry_space_group_name_H-M Aba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1, z+1/2' '-x+1/2, y+1, z+1/2' _cell_length_a 17.8309(7) _cell_length_b 21.5961(10) _cell_length_c 12.2832(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4730.0(3) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3429 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2176 _exptl_absorpt_coefficient_mu 1.261 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6007 _exptl_absorpt_correction_T_max 0.9169 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11202 _diffrn_reflns_av_R_equivalents 0.037 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.79 _diffrn_reflns_theta_max 67.15 _reflns_number_total 3838 _reflns_number_gt 3591 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+2.2293P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.47(12) _refine_ls_number_reflns 3838 _refine_ls_number_parameters 334 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.0984 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.020 _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 0.13111(14) 0.49793(12) 0.6429(2) 0.0376(5) Uani 1 1 d . . . H0 H 0.0897 0.5042 0.6954 0.045 Uiso 1 1 calc R . . N N 0.13456(12) 0.60493(9) 0.80341(16) 0.0432(5) Uani 1 1 d . . . H0A H 0.0992 0.5759 0.7839 0.052 Uiso 1 1 calc R . . C1 C 0.20102(13) 0.59483(10) 0.7255(2) 0.0391(5) Uani 1 1 d . . . H1 H 0.2343 0.5639 0.7603 0.047 Uiso 1 1 calc R . . C2 C 0.17098(13) 0.56521(10) 0.6216(2) 0.0386(5) Uani 1 1 d . . . H2A H 0.2124 0.5598 0.5701 0.046 Uiso 1 1 calc R . . H2B H 0.1344 0.5932 0.5882 0.046 Uiso 1 1 calc R . . C11 C 0.09638(14) 0.66639(13) 0.7929(3) 0.0560(7) Uani 1 1 d . . . H11A H 0.0824 0.6732 0.7167 0.067 Uiso 1 1 calc R . . H11B H 0.1312 0.6993 0.8144 0.067 Uiso 1 1 calc R . . C12 C 0.02642(18) 0.66970(19) 0.8639(3) 0.0760(10) Uani 1 1 d . . . H12A H 0.0050 0.7114 0.8597 0.091 Uiso 1 1 calc R . . H12B H -0.0111 0.6405 0.8364 0.091 Uiso 1 1 calc R . . C13 C 0.0443(2) 0.6544(2) 0.9815(3) 0.0963(15) Uani 1 1 d . . . H13A H 0.0760 0.6871 1.0123 0.116 Uiso 1 1 calc R . . H13B H -0.0023 0.6530 1.0237 0.116 Uiso 1 1 calc R . . C14 C 0.0842(3) 0.5930(3) 0.9905(3) 0.1023(14) Uani 1 1 d . . . H14A H 0.0983 0.5857 1.0666 0.123 Uiso 1 1 calc R . . H14B H 0.0501 0.5598 0.9681 0.123 Uiso 1 1 calc R . . C15 C 0.1532(2) 0.59157(18) 0.9207(2) 0.0737(9) Uani 1 1 d . . . H15A H 0.1768 0.5507 0.9261 0.088 Uiso 1 1 calc R . . H15B H 0.1891 0.6224 0.9472 0.088 Uiso 1 1 calc R . . C21 C 0.24715(12) 0.65332(10) 0.7109(2) 0.0395(5) Uani 1 1 d . . . C22 C 0.30497(14) 0.66640(11) 0.7835(3) 0.0527(7) Uani 1 1 d . . . H22 H 0.3135 0.6400 0.8431 0.063 Uiso 1 1 calc R . . C23 C 0.35019(15) 0.71823(12) 0.7687(3) 0.0611(8) Uani 1 1 d . . . H23 H 0.3888 0.7267 0.8185 0.073 Uiso 1 1 calc R . . C24 C 0.33889(15) 0.75686(12) 0.6823(3) 0.0566(7) Uani 1 1 d . . . H24 H 0.3698 0.7917 0.6725 0.068 Uiso 1 1 calc R . . C25 C 0.28239(16) 0.74465(12) 0.6101(2) 0.0540(7) Uani 1 1 d . . . H25 H 0.2747 0.7711 0.5504 0.065 Uiso 1 1 calc R . . C26 C 0.23591(14) 0.69305(11) 0.6245(2) 0.0461(6) Uani 1 1 d . . . H26 H 0.1968 0.6854 0.5749 0.055 Uiso 1 1 calc R . . C31 C 0.09563(12) 0.46616(10) 0.5326(2) 0.0372(5) Uani 1 1 d . . . C32 C 0.04930(13) 0.41453(10) 0.5421(2) 0.0391(5) Uani 1 1 d . . . F32 F 0.03524(8) 0.39087(7) 0.64217(12) 0.0510(4) Uani 1 1 d . . . C33 C 0.01578(13) 0.38462(11) 0.4561(2) 0.0455(6) Uani 1 1 d . . . F33 F -0.02816(10) 0.33459(8) 0.47348(16) 0.0638(4) Uani 1 1 d . . . C34 C 0.02629(14) 0.40594(13) 0.3525(2) 0.0489(6) Uani 1 1 d . . . F34 F -0.00734(10) 0.37803(9) 0.26740(14) 0.0703(5) Uani 1 1 d . . . C35 C 0.07153(14) 0.45659(12) 0.3370(2) 0.0453(6) Uani 1 1 d . . . F35 F 0.08151(10) 0.48005(8) 0.23623(12) 0.0610(4) Uani 1 1 d . . . C36 C 0.10499(13) 0.48443(10) 0.4254(2) 0.0408(5) Uani 1 1 d . . . F36 F 0.14919(9) 0.53377(7) 0.40097(13) 0.0541(4) Uani 1 1 d . . . C41 C 0.19001(13) 0.44797(11) 0.6961(2) 0.0391(5) Uani 1 1 d . . . C42 C 0.17827(16) 0.41857(12) 0.7949(2) 0.0484(6) Uani 1 1 d . . . F42 F 0.11733(11) 0.43289(8) 0.85558(13) 0.0654(5) Uani 1 1 d . . . C43 C 0.2240(2) 0.37338(13) 0.8361(3) 0.0623(8) Uani 1 1 d . . . F43 F 0.20746(16) 0.34380(8) 0.92925(16) 0.0954(8) Uani 1 1 d . . . C44 C 0.2870(2) 0.35661(12) 0.7790(3) 0.0656(9) Uani 1 1 d . . . F44 F 0.33312(14) 0.31210(8) 0.8182(2) 0.0978(8) Uani 1 1 d . . . C45 C 0.30329(15) 0.38448(13) 0.6822(3) 0.0586(8) Uani 1 1 d . . . F45 F 0.36482(10) 0.36850(9) 0.6272(2) 0.0852(6) Uani 1 1 d . . . C46 C 0.25464(14) 0.42959(10) 0.6434(2) 0.0444(5) Uani 1 1 d . . . F46 F 0.27258(9) 0.45613(7) 0.54666(14) 0.0586(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 0.0374(11) 0.0363(12) 0.0390(14) -0.0012(12) 0.0004(11) 0.0002(10) N 0.0480(11) 0.0426(11) 0.0391(11) -0.0050(9) -0.0032(9) -0.0089(8) C1 0.0418(11) 0.0316(11) 0.0441(13) 0.0004(10) -0.0034(10) 0.0007(9) C2 0.0425(11) 0.0336(11) 0.0398(13) -0.0009(9) -0.0026(10) 0.0030(9) C11 0.0449(13) 0.0540(15) 0.0689(18) -0.0075(14) 0.0033(14) 0.0035(11) C12 0.0496(16) 0.099(3) 0.079(2) -0.026(2) 0.0066(15) -0.0080(16) C13 0.073(2) 0.146(4) 0.070(2) -0.046(3) 0.016(2) -0.025(2) C14 0.121(3) 0.138(4) 0.0479(19) 0.001(2) 0.018(2) -0.010(3) C15 0.096(2) 0.086(2) 0.0395(16) 0.0055(15) -0.0047(16) 0.0030(19) C21 0.0374(11) 0.0317(11) 0.0493(14) -0.0018(10) -0.0012(10) 0.0030(9) C22 0.0482(13) 0.0372(12) 0.0728(19) 0.0043(13) -0.0144(14) -0.0002(10) C23 0.0425(13) 0.0440(14) 0.097(2) -0.0061(16) -0.0126(14) -0.0051(11) C24 0.0512(14) 0.0339(13) 0.085(2) -0.0024(13) 0.0117(15) -0.0019(11) C25 0.0636(16) 0.0358(13) 0.0626(18) 0.0040(12) 0.0129(14) 0.0033(11) C26 0.0500(12) 0.0408(12) 0.0474(15) 0.0004(11) -0.0011(11) 0.0018(10) C31 0.0355(10) 0.0329(11) 0.0433(13) 0.0003(10) -0.0019(10) 0.0023(8) C32 0.0409(11) 0.0358(11) 0.0405(12) 0.0029(10) 0.0020(10) -0.0003(9) F32 0.0602(8) 0.0464(8) 0.0465(8) 0.0059(7) 0.0015(7) -0.0132(6) C33 0.0382(12) 0.0413(13) 0.0570(15) -0.0080(11) -0.0004(11) -0.0067(10) F33 0.0662(9) 0.0548(9) 0.0703(10) -0.0122(8) 0.0020(8) -0.0239(8) C34 0.0441(13) 0.0550(15) 0.0476(15) -0.0135(13) -0.0021(11) -0.0029(11) F34 0.0682(10) 0.0894(13) 0.0534(10) -0.0232(9) -0.0089(8) -0.0177(10) C35 0.0444(12) 0.0524(14) 0.0391(13) -0.0012(11) 0.0012(10) 0.0056(11) F35 0.0698(10) 0.0736(11) 0.0397(8) 0.0031(8) 0.0001(7) -0.0008(8) C36 0.0386(11) 0.0387(11) 0.0452(14) -0.0017(10) 0.0007(10) -0.0011(9) F36 0.0663(9) 0.0492(8) 0.0466(8) 0.0067(7) 0.0021(7) -0.0159(7) C41 0.0439(12) 0.0310(11) 0.0423(12) -0.0041(10) -0.0072(10) -0.0051(9) C42 0.0623(15) 0.0408(12) 0.0419(14) -0.0029(11) -0.0098(12) -0.0092(11) F42 0.0802(11) 0.0705(10) 0.0455(9) 0.0060(8) 0.0069(8) -0.0118(9) C43 0.100(2) 0.0393(13) 0.0476(15) 0.0051(12) -0.0293(17) -0.0055(15) F43 0.176(2) 0.0533(10) 0.0568(11) 0.0177(9) -0.0257(13) -0.0038(12) C44 0.091(2) 0.0333(13) 0.072(2) -0.0014(14) -0.0441(19) 0.0068(14) F44 0.1299(18) 0.0487(9) 0.1147(17) -0.0037(11) -0.0679(15) 0.0284(11) C45 0.0537(15) 0.0452(14) 0.077(2) -0.0167(14) -0.0171(14) 0.0093(12) F45 0.0631(10) 0.0749(12) 0.1177(17) -0.0279(12) -0.0171(11) 0.0282(9) C46 0.0469(12) 0.0380(11) 0.0482(14) -0.0050(11) -0.0108(11) 0.0004(10) F46 0.0576(9) 0.0573(9) 0.0610(10) -0.0004(8) 0.0153(8) 0.0094(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B C2 1.638(3) . ? B C41 1.642(4) . ? B C31 1.644(3) . ? B H0 0.9900 . ? N C11 1.497(3) . ? N C15 1.506(4) . ? N C1 1.539(3) . ? N H0A 0.9200 . ? C1 C21 1.518(3) . ? C1 C2 1.524(3) . ? C1 H1 0.9900 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C11 C12 1.523(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C12 C13 1.516(6) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C13 C14 1.509(7) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C14 C15 1.500(5) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C21 C26 1.380(4) . ? C21 C22 1.392(4) . ? C22 C23 1.392(4) . ? C22 H22 0.9400 . ? C23 C24 1.364(5) . ? C23 H23 0.9400 . ? C24 C25 1.368(4) . ? C24 H24 0.9400 . ? C25 C26 1.400(4) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? C31 C36 1.385(4) . ? C31 C32 1.393(3) . ? C32 F32 1.354(3) . ? C32 C33 1.375(4) . ? C33 F33 1.352(3) . ? C33 C34 1.365(4) . ? C34 F34 1.348(3) . ? C34 C35 1.372(4) . ? C35 F35 1.350(3) . ? C35 C36 1.377(4) . ? C36 F36 1.359(3) . ? C41 C46 1.380(4) . ? C41 C42 1.386(4) . ? C42 F42 1.353(3) . ? C42 C43 1.368(4) . ? C43 F43 1.343(4) . ? C43 C44 1.373(5) . ? C44 F44 1.353(3) . ? C44 C45 1.364(5) . ? C45 F45 1.334(4) . ? C45 C46 1.389(4) . ? C46 F46 1.357(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 C2 B C41 111.63(18) . . ? C2 B C31 113.95(19) . . ? C41 B C31 107.45(19) . . ? C2 B H0 107.9 . . ? C41 B H0 107.9 . . ? C31 B H0 107.9 . . ? C11 N C15 110.6(2) . . ? C11 N C1 114.98(19) . . ? C15 N C1 113.4(2) . . ? C11 N H0A 105.6 . . ? C15 N H0A 105.6 . . ? C1 N H0A 105.6 . . ? C21 C1 C2 116.2(2) . . ? C21 C1 N 111.88(18) . . ? C2 C1 N 108.02(18) . . ? C21 C1 H1 106.7 . . ? C2 C1 H1 106.7 . . ? N C1 H1 106.7 . . ? C1 C2 B 113.05(19) . . ? C1 C2 H2A 109.0 . . ? B C2 H2A 109.0 . . ? C1 C2 H2B 109.0 . . ? B C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? N C11 C12 111.4(3) . . ? N C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? N C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C13 C12 C11 111.3(3) . . ? C13 C12 H12A 109.4 . . ? C11 C12 H12A 109.4 . . ? C13 C12 H12B 109.4 . . ? C11 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C14 C13 C12 111.1(3) . . ? C14 C13 H13A 109.4 . . ? C12 C13 H13A 109.4 . . ? C14 C13 H13B 109.4 . . ? C12 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? C15 C14 C13 111.3(4) . . ? C15 C14 H14A 109.4 . . ? C13 C14 H14A 109.4 . . ? C15 C14 H14B 109.4 . . ? C13 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? C14 C15 N 111.2(3) . . ? C14 C15 H15A 109.4 . . ? N C15 H15A 109.4 . . ? C14 C15 H15B 109.4 . . ? N C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C26 C21 C22 118.3(2) . . ? C26 C21 C1 122.0(2) . . ? C22 C21 C1 119.7(2) . . ? C21 C22 C23 120.6(3) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C24 C23 C22 120.5(3) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C25 119.7(2) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C24 C25 C26 120.5(3) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C21 C26 C25 120.4(2) . . ? C21 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? C36 C31 C32 112.3(2) . . ? C36 C31 B 128.1(2) . . ? C32 C31 B 119.6(2) . . ? F32 C32 C33 116.1(2) . . ? F32 C32 C31 119.2(2) . . ? C33 C32 C31 124.7(2) . . ? F33 C33 C34 119.8(2) . . ? F33 C33 C32 120.4(2) . . ? C34 C33 C32 119.8(2) . . ? F34 C34 C33 120.7(2) . . ? F34 C34 C35 120.7(2) . . ? C33 C34 C35 118.6(2) . . ? F35 C35 C34 120.3(2) . . ? F35 C35 C36 120.1(2) . . ? C34 C35 C36 119.6(2) . . ? F36 C36 C35 114.8(2) . . ? F36 C36 C31 120.2(2) . . ? C35 C36 C31 125.0(2) . . ? C46 C41 C42 113.9(2) . . ? C46 C41 B 122.4(2) . . ? C42 C41 B 123.6(2) . . ? F42 C42 C43 115.9(3) . . ? F42 C42 C41 119.9(2) . . ? C43 C42 C41 124.1(3) . . ? F43 C43 C42 121.6(3) . . ? F43 C43 C44 119.3(3) . . ? C42 C43 C44 119.1(3) . . ? F44 C44 C45 119.6(3) . . ? F44 C44 C43 120.2(3) . . ? C45 C44 C43 120.2(3) . . ? F45 C45 C44 120.2(3) . . ? F45 C45 C46 121.4(3) . . ? C44 C45 C46 118.4(3) . . ? F46 C46 C41 119.1(2) . . ? F46 C46 C45 116.7(2) . . ? C41 C46 C45 124.2(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N C1 C21 38.4(3) . . . . ? C15 N C1 C21 -90.3(3) . . . . ? C11 N C1 C2 -90.6(2) . . . . ? C15 N C1 C2 140.6(2) . . . . ? C21 C1 C2 B 172.70(18) . . . . ? N C1 C2 B -60.7(2) . . . . ? C41 B C2 C1 -60.1(3) . . . . ? C31 B C2 C1 177.98(18) . . . . ? C15 N C11 C12 -56.1(3) . . . . ? C1 N C11 C12 173.8(2) . . . . ? N C11 C12 C13 54.6(4) . . . . ? C11 C12 C13 C14 -53.6(4) . . . . ? C12 C13 C14 C15 55.0(5) . . . . ? C13 C14 C15 N -56.9(4) . . . . ? C11 N C15 C14 57.4(4) . . . . ? C1 N C15 C14 -171.7(3) . . . . ? C2 C1 C21 C26 28.7(3) . . . . ? N C1 C21 C26 -95.9(3) . . . . ? C2 C1 C21 C22 -148.3(2) . . . . ? N C1 C21 C22 87.1(3) . . . . ? C26 C21 C22 C23 -0.1(4) . . . . ? C1 C21 C22 C23 177.0(2) . . . . ? C21 C22 C23 C24 -0.4(4) . . . . ? C22 C23 C24 C25 0.3(4) . . . . ? C23 C24 C25 C26 0.3(4) . . . . ? C22 C21 C26 C25 0.8(4) . . . . ? C1 C21 C26 C25 -176.2(2) . . . . ? C24 C25 C26 C21 -0.9(4) . . . . ? C2 B C31 C36 10.3(3) . . . . ? C41 B C31 C36 -113.9(3) . . . . ? C2 B C31 C32 -169.1(2) . . . . ? C41 B C31 C32 66.7(3) . . . . ? C36 C31 C32 F32 179.5(2) . . . . ? B C31 C32 F32 -1.0(3) . . . . ? C36 C31 C32 C33 -0.4(3) . . . . ? B C31 C32 C33 179.1(2) . . . . ? F32 C32 C33 F33 -0.1(3) . . . . ? C31 C32 C33 F33 179.8(2) . . . . ? F32 C32 C33 C34 179.2(2) . . . . ? C31 C32 C33 C34 -0.9(4) . . . . ? F33 C33 C34 F34 0.7(4) . . . . ? C32 C33 C34 F34 -178.6(2) . . . . ? F33 C33 C34 C35 -179.6(2) . . . . ? C32 C33 C34 C35 1.1(4) . . . . ? F34 C34 C35 F35 1.6(4) . . . . ? C33 C34 C35 F35 -178.1(2) . . . . ? F34 C34 C35 C36 179.7(2) . . . . ? C33 C34 C35 C36 0.0(4) . . . . ? F35 C35 C36 F36 -2.5(3) . . . . ? C34 C35 C36 F36 179.4(2) . . . . ? F35 C35 C36 C31 176.7(2) . . . . ? C34 C35 C36 C31 -1.5(4) . . . . ? C32 C31 C36 F36 -179.33(19) . . . . ? B C31 C36 F36 1.2(4) . . . . ? C32 C31 C36 C35 1.5(3) . . . . ? B C31 C36 C35 -177.9(2) . . . . ? C2 B C41 C46 -61.1(3) . . . . ? C31 B C41 C46 64.6(3) . . . . ? C2 B C41 C42 121.7(2) . . . . ? C31 B C41 C42 -112.6(2) . . . . ? C46 C41 C42 F42 179.2(2) . . . . ? B C41 C42 F42 -3.4(3) . . . . ? C46 C41 C42 C43 -2.7(3) . . . . ? B C41 C42 C43 174.7(2) . . . . ? F42 C42 C43 F43 2.2(4) . . . . ? C41 C42 C43 F43 -175.9(2) . . . . ? F42 C42 C43 C44 -179.8(2) . . . . ? C41 C42 C43 C44 2.1(4) . . . . ? F43 C43 C44 F44 -2.0(4) . . . . ? C42 C43 C44 F44 179.9(2) . . . . ? F43 C43 C44 C45 177.6(3) . . . . ? C42 C43 C44 C45 -0.5(4) . . . . ? F44 C44 C45 F45 -0.8(4) . . . . ? C43 C44 C45 F45 179.5(3) . . . . ? F44 C44 C45 C46 179.4(2) . . . . ? C43 C44 C45 C46 -0.3(4) . . . . ? C42 C41 C46 F46 -178.9(2) . . . . ? B C41 C46 F46 3.7(3) . . . . ? C42 C41 C46 C45 1.9(3) . . . . ? B C41 C46 C45 -175.5(2) . . . . ? F45 C45 C46 F46 0.4(4) . . . . ? C44 C45 C46 F46 -179.8(2) . . . . ? F45 C45 C46 C41 179.7(2) . . . . ? C44 C45 C46 C41 -0.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 67.15 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.205 _refine_diff_density_min -0.178 _refine_diff_density_rms 0.040 # Attachment '- 11d.cif' data_erk5378 _database_code_depnum_ccdc_archive 'CCDC 815788' #TrackingRef '- 11d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H22 B F10 N' _chemical_formula_weight 513.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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 P21/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 12.1379(4) _cell_length_b 14.0463(5) _cell_length_c 13.5423(5) _cell_angle_alpha 90.00 _cell_angle_beta 105.934(2) _cell_angle_gamma 90.00 _cell_volume 2220.15(14) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4035 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.535 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 1.311 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7352 _exptl_absorpt_correction_T_max 0.8276 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32849 _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_av_sigmaI/netI 0.0187 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.34 _diffrn_reflns_theta_max 67.63 _reflns_number_total 3968 _reflns_number_gt 3647 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0474P)^2^+0.7536P] 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 3968 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0996 _refine_ls_wR_factor_gt 0.0967 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 N N 0.12519(10) 0.18548(9) 0.29720(10) 0.0384(3) Uani 1 1 d . . . H0 H 0.1857 0.1439 0.3061 0.046 Uiso 1 1 calc R . . B B 0.32861(14) 0.17212(12) 0.21127(12) 0.0357(3) Uani 1 1 d . . . H0A H 0.3151 0.1373 0.2704 0.043 Uiso 1 1 calc R . . C1 C 0.11456(13) 0.23347(11) 0.19412(12) 0.0393(3) Uani 1 1 d . . . H1 H 0.0819 0.1859 0.1401 0.047 Uiso 1 1 calc R . . C2 C 0.23422(12) 0.25969(10) 0.18469(11) 0.0365(3) Uani 1 1 d . . . H2 H 0.2640 0.3111 0.2350 0.044 Uiso 1 1 calc R . . C11 C 0.02472(15) 0.12541(13) 0.30132(15) 0.0520(4) Uani 1 1 d . . . H11A H 0.0055 0.0820 0.2424 0.062 Uiso 1 1 calc R . . H11B H -0.0418 0.1663 0.2973 0.062 Uiso 1 1 calc R . . C12 C 0.05165(19) 0.06882(14) 0.39936(16) 0.0627(5) Uani 1 1 d . . . H12A H 0.1130 0.0234 0.3996 0.075 Uiso 1 1 calc R . . H12B H -0.0163 0.0324 0.4021 0.075 Uiso 1 1 calc R . . C13 C 0.0886(2) 0.13170(14) 0.49407(16) 0.0676(6) Uani 1 1 d . . . H13A H 0.0242 0.1715 0.4994 0.081 Uiso 1 1 calc R . . H13B H 0.1120 0.0920 0.5558 0.081 Uiso 1 1 calc R . . C14 C 0.1873(2) 0.19404(15) 0.48657(14) 0.0678(6) Uani 1 1 d . . . H14A H 0.2543 0.1542 0.4892 0.081 Uiso 1 1 calc R . . H14B H 0.2073 0.2376 0.5453 0.081 Uiso 1 1 calc R . . C15 C 0.15707(19) 0.25111(13) 0.38787(14) 0.0587(5) Uani 1 1 d . . . H15A H 0.0927 0.2937 0.3867 0.070 Uiso 1 1 calc R . . H15B H 0.2227 0.2902 0.3844 0.070 Uiso 1 1 calc R . . C21 C 0.03180(15) 0.31747(13) 0.17676(15) 0.0538(4) Uani 1 1 d . . . H21A H 0.0602 0.3656 0.2300 0.065 Uiso 1 1 calc R . . H21B H -0.0434 0.2959 0.1813 0.065 Uiso 1 1 calc R . . C22 C 0.02050(16) 0.36095(14) 0.07105(15) 0.0592(5) Uani 1 1 d . . . H22A H -0.0154 0.3147 0.0177 0.071 Uiso 1 1 calc R . . H22B H -0.0289 0.4173 0.0621 0.071 Uiso 1 1 calc R . . C23 C 0.13669(16) 0.38895(12) 0.05946(13) 0.0525(4) Uani 1 1 d . . . H23A H 0.1700 0.4389 0.1092 0.063 Uiso 1 1 calc R . . H23B H 0.1280 0.4145 -0.0096 0.063 Uiso 1 1 calc R . . C24 C 0.21664(15) 0.30306(11) 0.07697(12) 0.0444(4) Uani 1 1 d . . . H24A H 0.2910 0.3225 0.0685 0.053 Uiso 1 1 calc R . . H24B H 0.1846 0.2545 0.0251 0.053 Uiso 1 1 calc R . . C31 C 0.30548(13) 0.09559(10) 0.11540(11) 0.0374(3) Uani 1 1 d . . . C32 C 0.36252(13) 0.09448(11) 0.03930(12) 0.0412(3) Uani 1 1 d . . . F32 F 0.44571(8) 0.15892(7) 0.04089(7) 0.0527(3) Uani 1 1 d . . . C33 C 0.34149(15) 0.02985(12) -0.04047(12) 0.0477(4) Uani 1 1 d . . . F33 F 0.40234(10) 0.03208(8) -0.10959(8) 0.0640(3) Uani 1 1 d . . . C34 C 0.25652(16) -0.03662(12) -0.04951(13) 0.0510(4) Uani 1 1 d . . . F34 F 0.23198(11) -0.09891(8) -0.12807(9) 0.0723(3) Uani 1 1 d . . . C35 C 0.19596(15) -0.03852(11) 0.02208(14) 0.0497(4) Uani 1 1 d . . . F35 F 0.11178(10) -0.10345(7) 0.01392(10) 0.0700(3) Uani 1 1 d . . . C36 C 0.22250(13) 0.02550(11) 0.10249(13) 0.0423(3) Uani 1 1 d . . . F36 F 0.16158(9) 0.01653(7) 0.17243(8) 0.0555(3) Uani 1 1 d . . . C41 C 0.46331(13) 0.20537(10) 0.24558(10) 0.0362(3) Uani 1 1 d . . . C42 C 0.54801(13) 0.13687(11) 0.27894(11) 0.0398(3) Uani 1 1 d . . . F42 F 0.51701(8) 0.04500(6) 0.28363(8) 0.0517(2) Uani 1 1 d . . . C43 C 0.66411(14) 0.15513(13) 0.30778(12) 0.0470(4) Uani 1 1 d . . . F43 F 0.74059(9) 0.08473(8) 0.33992(9) 0.0656(3) Uani 1 1 d . . . C44 C 0.70184(13) 0.24700(13) 0.30422(13) 0.0481(4) Uani 1 1 d . . . F44 F 0.81447(8) 0.26685(9) 0.33186(10) 0.0706(3) Uani 1 1 d . . . C45 C 0.62283(14) 0.31790(12) 0.27285(12) 0.0443(4) Uani 1 1 d . . . F45 F 0.65805(9) 0.40866(7) 0.26782(8) 0.0607(3) Uani 1 1 d . . . C46 C 0.50740(13) 0.29661(11) 0.24571(11) 0.0394(3) Uani 1 1 d . . . F46 F 0.43793(8) 0.37274(6) 0.21653(8) 0.0555(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 N 0.0378(6) 0.0364(6) 0.0439(7) -0.0055(5) 0.0160(5) -0.0044(5) B 0.0397(9) 0.0345(8) 0.0359(8) 0.0042(6) 0.0151(7) -0.0001(7) C1 0.0382(8) 0.0389(8) 0.0400(8) -0.0040(6) 0.0090(6) 0.0008(6) C2 0.0389(8) 0.0355(7) 0.0356(7) -0.0007(6) 0.0112(6) 0.0005(6) C11 0.0426(9) 0.0543(10) 0.0653(11) -0.0128(8) 0.0253(8) -0.0141(7) C12 0.0769(13) 0.0509(10) 0.0719(12) -0.0051(9) 0.0403(11) -0.0205(9) C13 0.0976(16) 0.0571(11) 0.0620(11) -0.0056(9) 0.0455(11) -0.0148(11) C14 0.0932(15) 0.0673(12) 0.0454(10) -0.0085(9) 0.0230(10) -0.0274(11) C15 0.0853(13) 0.0483(10) 0.0478(10) -0.0130(8) 0.0272(9) -0.0250(9) C21 0.0463(9) 0.0513(10) 0.0658(11) 0.0027(8) 0.0190(8) 0.0123(8) C22 0.0561(11) 0.0539(10) 0.0608(11) 0.0035(8) 0.0048(8) 0.0205(8) C23 0.0677(11) 0.0445(9) 0.0433(9) 0.0068(7) 0.0116(8) 0.0112(8) C24 0.0517(9) 0.0429(8) 0.0392(8) 0.0039(6) 0.0133(7) 0.0054(7) C31 0.0380(8) 0.0337(7) 0.0404(8) 0.0035(6) 0.0107(6) 0.0062(6) C32 0.0389(8) 0.0430(8) 0.0408(8) 0.0026(6) 0.0092(6) 0.0039(6) F32 0.0519(5) 0.0652(6) 0.0456(5) -0.0007(4) 0.0211(4) -0.0093(5) C33 0.0508(9) 0.0527(9) 0.0381(8) 0.0004(7) 0.0099(7) 0.0172(8) F33 0.0693(7) 0.0817(7) 0.0449(5) -0.0047(5) 0.0226(5) 0.0191(6) C34 0.0606(10) 0.0419(9) 0.0430(9) -0.0064(7) 0.0013(8) 0.0136(8) F34 0.0944(9) 0.0548(6) 0.0565(6) -0.0197(5) 0.0019(6) 0.0102(6) C35 0.0485(9) 0.0333(8) 0.0598(10) -0.0012(7) 0.0022(8) 0.0013(7) F35 0.0666(7) 0.0460(6) 0.0883(8) -0.0088(5) 0.0061(6) -0.0150(5) C36 0.0428(8) 0.0352(8) 0.0500(9) 0.0020(6) 0.0144(7) 0.0036(6) F36 0.0568(6) 0.0455(5) 0.0724(7) -0.0026(5) 0.0317(5) -0.0103(4) C41 0.0401(8) 0.0391(8) 0.0307(7) 0.0009(6) 0.0120(6) 0.0022(6) C42 0.0453(8) 0.0401(8) 0.0348(7) -0.0007(6) 0.0122(6) 0.0033(6) F42 0.0560(6) 0.0381(5) 0.0590(6) 0.0052(4) 0.0122(4) 0.0080(4) C43 0.0418(8) 0.0600(10) 0.0382(8) -0.0039(7) 0.0094(6) 0.0132(7) F43 0.0491(6) 0.0739(7) 0.0690(7) -0.0009(5) 0.0080(5) 0.0245(5) C44 0.0357(8) 0.0668(11) 0.0415(8) -0.0097(7) 0.0100(6) -0.0036(7) F44 0.0368(5) 0.0910(8) 0.0812(8) -0.0183(6) 0.0117(5) -0.0061(5) C45 0.0460(9) 0.0497(9) 0.0384(8) -0.0058(7) 0.0135(7) -0.0097(7) F45 0.0576(6) 0.0575(6) 0.0644(6) -0.0038(5) 0.0122(5) -0.0209(5) C46 0.0420(8) 0.0397(8) 0.0365(7) 0.0014(6) 0.0109(6) 0.0015(6) F46 0.0496(5) 0.0377(5) 0.0760(7) 0.0092(4) 0.0118(5) 0.0000(4) _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 N C11 1.4965(19) . ? N C15 1.499(2) . ? N C1 1.523(2) . ? N H0 0.9200 . ? B C41 1.640(2) . ? B C31 1.649(2) . ? B C2 1.652(2) . ? B H0A 0.9900 . ? C1 C21 1.525(2) . ? C1 C2 1.537(2) . ? C1 H1 0.9900 . ? C2 C24 1.541(2) . ? C2 H2 0.9900 . ? C11 C12 1.504(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C12 C13 1.520(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C13 C14 1.510(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C14 C15 1.515(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C21 C22 1.527(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C22 C23 1.513(3) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C23 C24 1.525(2) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C31 C36 1.385(2) . ? C31 C32 1.390(2) . ? C32 F32 1.3518(18) . ? C32 C33 1.380(2) . ? C33 F33 1.342(2) . ? C33 C34 1.372(3) . ? C34 F34 1.3461(19) . ? C34 C35 1.368(3) . ? C35 F35 1.351(2) . ? C35 C36 1.380(2) . ? C36 F36 1.3580(19) . ? C41 C46 1.389(2) . ? C41 C42 1.390(2) . ? C42 F42 1.3507(18) . ? C42 C43 1.379(2) . ? C43 F43 1.3443(19) . ? C43 C44 1.375(3) . ? C44 F44 1.3438(19) . ? C44 C45 1.367(2) . ? C45 F45 1.3523(19) . ? C45 C46 1.380(2) . ? C46 F46 1.3519(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 C11 N C15 110.24(13) . . ? C11 N C1 114.76(12) . . ? C15 N C1 114.61(12) . . ? C11 N H0 105.4 . . ? C15 N H0 105.4 . . ? C1 N H0 105.4 . . ? C41 B C31 110.47(12) . . ? C41 B C2 115.31(12) . . ? C31 B C2 110.85(12) . . ? C41 B H0A 106.6 . . ? C31 B H0A 106.6 . . ? C2 B H0A 106.6 . . ? N C1 C21 111.72(13) . . ? N C1 C2 109.75(11) . . ? C21 C1 C2 113.52(13) . . ? N C1 H1 107.2 . . ? C21 C1 H1 107.2 . . ? C2 C1 H1 107.2 . . ? C1 C2 C24 106.56(12) . . ? C1 C2 B 114.72(12) . . ? C24 C2 B 114.09(12) . . ? C1 C2 H2 107.0 . . ? C24 C2 H2 107.0 . . ? B C2 H2 107.0 . . ? N C11 C12 110.43(15) . . ? N C11 H11A 109.6 . . ? C12 C11 H11A 109.6 . . ? N C11 H11B 109.6 . . ? C12 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? C11 C12 C13 112.33(16) . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.9 . . ? C14 C13 C12 109.62(15) . . ? C14 C13 H13A 109.7 . . ? C12 C13 H13A 109.7 . . ? C14 C13 H13B 109.7 . . ? C12 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? C13 C14 C15 111.23(18) . . ? C13 C14 H14A 109.4 . . ? C15 C14 H14A 109.4 . . ? C13 C14 H14B 109.4 . . ? C15 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? N C15 C14 110.06(15) . . ? N C15 H15A 109.6 . . ? C14 C15 H15A 109.6 . . ? N C15 H15B 109.6 . . ? C14 C15 H15B 109.6 . . ? H15A C15 H15B 108.2 . . ? C1 C21 C22 109.86(14) . . ? C1 C21 H21A 109.7 . . ? C22 C21 H21A 109.7 . . ? C1 C21 H21B 109.7 . . ? C22 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? C23 C22 C21 110.78(15) . . ? C23 C22 H22A 109.5 . . ? C21 C22 H22A 109.5 . . ? C23 C22 H22B 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 108.1 . . ? C22 C23 C24 110.46(14) . . ? C22 C23 H23A 109.6 . . ? C24 C23 H23A 109.6 . . ? C22 C23 H23B 109.6 . . ? C24 C23 H23B 109.6 . . ? H23A C23 H23B 108.1 . . ? C23 C24 C2 112.13(13) . . ? C23 C24 H24A 109.2 . . ? C2 C24 H24A 109.2 . . ? C23 C24 H24B 109.2 . . ? C2 C24 H24B 109.2 . . ? H24A C24 H24B 107.9 . . ? C36 C31 C32 113.04(14) . . ? C36 C31 B 121.56(13) . . ? C32 C31 B 125.38(13) . . ? F32 C32 C33 115.44(14) . . ? F32 C32 C31 120.16(14) . . ? C33 C32 C31 124.39(15) . . ? F33 C33 C34 119.85(15) . . ? F33 C33 C32 120.77(16) . . ? C34 C33 C32 119.38(16) . . ? F34 C34 C35 120.13(17) . . ? F34 C34 C33 120.72(17) . . ? C35 C34 C33 119.15(15) . . ? F35 C35 C34 119.77(15) . . ? F35 C35 C36 120.78(17) . . ? C34 C35 C36 119.46(16) . . ? F36 C36 C35 115.84(14) . . ? F36 C36 C31 119.63(14) . . ? C35 C36 C31 124.53(15) . . ? C46 C41 C42 112.83(14) . . ? C46 C41 B 128.10(13) . . ? C42 C41 B 119.07(13) . . ? F42 C42 C43 116.14(14) . . ? F42 C42 C41 119.07(13) . . ? C43 C42 C41 124.79(15) . . ? F43 C43 C44 119.66(15) . . ? F43 C43 C42 121.07(16) . . ? C44 C43 C42 119.27(15) . . ? F44 C44 C45 120.58(16) . . ? F44 C44 C43 120.55(16) . . ? C45 C44 C43 118.87(15) . . ? F45 C45 C44 119.87(14) . . ? F45 C45 C46 120.18(15) . . ? C44 C45 C46 119.95(15) . . ? F46 C46 C45 114.37(13) . . ? F46 C46 C41 121.36(13) . . ? C45 C46 C41 124.26(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N C1 C21 74.74(17) . . . . ? C15 N C1 C21 -54.33(18) . . . . ? C11 N C1 C2 -158.43(12) . . . . ? C15 N C1 C2 72.50(16) . . . . ? N C1 C2 C24 177.27(11) . . . . ? C21 C1 C2 C24 -56.92(16) . . . . ? N C1 C2 B 50.00(16) . . . . ? C21 C1 C2 B 175.81(13) . . . . ? C41 B C2 C1 -157.19(12) . . . . ? C31 B C2 C1 76.37(15) . . . . ? C41 B C2 C24 79.49(16) . . . . ? C31 B C2 C24 -46.95(16) . . . . ? C15 N C11 C12 -58.19(19) . . . . ? C1 N C11 C12 170.60(13) . . . . ? N C11 C12 C13 56.1(2) . . . . ? C11 C12 C13 C14 -54.2(2) . . . . ? C12 C13 C14 C15 55.1(2) . . . . ? C11 N C15 C14 59.5(2) . . . . ? C1 N C15 C14 -169.24(15) . . . . ? C13 C14 C15 N -58.5(2) . . . . ? N C1 C21 C22 -177.91(14) . . . . ? C2 C1 C21 C22 57.34(19) . . . . ? C1 C21 C22 C23 -55.6(2) . . . . ? C21 C22 C23 C24 57.12(19) . . . . ? C22 C23 C24 C2 -59.39(19) . . . . ? C1 C2 C24 C23 57.27(17) . . . . ? B C2 C24 C23 -175.10(13) . . . . ? C41 B C31 C36 149.69(13) . . . . ? C2 B C31 C36 -81.24(16) . . . . ? C41 B C31 C32 -31.72(19) . . . . ? C2 B C31 C32 97.36(16) . . . . ? C36 C31 C32 F32 179.67(13) . . . . ? B C31 C32 F32 1.0(2) . . . . ? C36 C31 C32 C33 -1.1(2) . . . . ? B C31 C32 C33 -179.80(14) . . . . ? F32 C32 C33 F33 0.9(2) . . . . ? C31 C32 C33 F33 -178.35(14) . . . . ? F32 C32 C33 C34 -178.38(14) . . . . ? C31 C32 C33 C34 2.4(2) . . . . ? F33 C33 C34 F34 -1.1(2) . . . . ? C32 C33 C34 F34 178.21(14) . . . . ? F33 C33 C34 C35 179.41(14) . . . . ? C32 C33 C34 C35 -1.3(2) . . . . ? F34 C34 C35 F35 0.3(2) . . . . ? C33 C34 C35 F35 179.81(14) . . . . ? F34 C34 C35 C36 179.67(14) . . . . ? C33 C34 C35 C36 -0.8(2) . . . . ? F35 C35 C36 F36 1.9(2) . . . . ? C34 C35 C36 F36 -177.49(14) . . . . ? F35 C35 C36 C31 -178.47(14) . . . . ? C34 C35 C36 C31 2.2(2) . . . . ? C32 C31 C36 F36 178.47(13) . . . . ? B C31 C36 F36 -2.8(2) . . . . ? C32 C31 C36 C35 -1.2(2) . . . . ? B C31 C36 C35 177.57(14) . . . . ? C31 B C41 C46 120.04(15) . . . . ? C2 B C41 C46 -6.6(2) . . . . ? C31 B C41 C42 -59.60(16) . . . . ? C2 B C41 C42 173.77(13) . . . . ? C46 C41 C42 F42 179.34(12) . . . . ? B C41 C42 F42 -1.0(2) . . . . ? C46 C41 C42 C43 -1.1(2) . . . . ? B C41 C42 C43 178.57(14) . . . . ? F42 C42 C43 F43 -0.9(2) . . . . ? C41 C42 C43 F43 179.51(14) . . . . ? F42 C42 C43 C44 179.56(14) . . . . ? C41 C42 C43 C44 0.0(2) . . . . ? F43 C43 C44 F44 0.5(2) . . . . ? C42 C43 C44 F44 -179.99(14) . . . . ? F43 C43 C44 C45 -179.00(14) . . . . ? C42 C43 C44 C45 0.5(2) . . . . ? F44 C44 C45 F45 1.1(2) . . . . ? C43 C44 C45 F45 -179.36(14) . . . . ? F44 C44 C45 C46 -179.32(14) . . . . ? C43 C44 C45 C46 0.2(2) . . . . ? F45 C45 C46 F46 -0.8(2) . . . . ? C44 C45 C46 F46 179.71(14) . . . . ? F45 C45 C46 C41 178.06(14) . . . . ? C44 C45 C46 C41 -1.5(2) . . . . ? C42 C41 C46 F46 -179.41(13) . . . . ? B C41 C46 F46 0.9(2) . . . . ? C42 C41 C46 C45 1.9(2) . . . . ? B C41 C46 C45 -177.80(14) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 67.63 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.383 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.036 # Attachment '- 11e.cif' data_erk5445 _database_code_depnum_ccdc_archive 'CCDC 815789' #TrackingRef '- 11e.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H20 B F10 N' _chemical_formula_weight 499.20 _chemical_absolute_configuration ad 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 orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.9724(4) _cell_length_b 11.3362(5) _cell_length_c 16.9960(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2114.05(15) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3025 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.35 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 1.360 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7727 _exptl_absorpt_correction_T_max 0.8760 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10207 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.69 _diffrn_reflns_theta_max 66.92 _reflns_number_total 3563 _reflns_number_gt 3354 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0431P)^2^+0.8350P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.12(12) _refine_ls_number_reflns 3563 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0397 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0917 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B B 0.3382(2) 0.1518(2) 0.22428(15) 0.0324(5) Uani 1 1 d . . . H0 H 0.3340 0.2112 0.2669 0.039 Uiso 1 1 calc R . . N N 0.21570(17) 0.12606(17) 0.38064(11) 0.0359(4) Uani 1 1 d . . . H0A H 0.2764 0.1756 0.3633 0.043 Uiso 1 1 calc R . . C1 C 0.2251(2) 0.0169(2) 0.32914(14) 0.0368(5) Uani 1 1 d . . . H1 H 0.3038 -0.0217 0.3413 0.044 Uiso 1 1 calc R . . C2 C 0.2293(2) 0.0549(2) 0.24241(13) 0.0339(5) Uani 1 1 d . . . H2 H 0.1505 0.0932 0.2301 0.041 Uiso 1 1 calc R . . C11 C 0.2396(3) 0.1094(2) 0.46698(14) 0.0473(6) Uani 1 1 d . . . H11A H 0.2011 0.0369 0.4863 0.057 Uiso 1 1 calc R . . H11B H 0.3272 0.1057 0.4777 0.057 Uiso 1 1 calc R . . C12 C 0.1836(3) 0.2160(2) 0.50448(15) 0.0520(7) Uani 1 1 d . . . H12A H 0.2380 0.2843 0.5007 0.062 Uiso 1 1 calc R . . H12B H 0.1646 0.2014 0.5600 0.062 Uiso 1 1 calc R . . C13 C 0.0696(3) 0.2345(4) 0.45718(19) 0.0760(10) Uani 1 1 d . . . H13A H 0.0453 0.3177 0.4584 0.091 Uiso 1 1 calc R . . H13B H 0.0027 0.1868 0.4783 0.091 Uiso 1 1 calc R . . C14 C 0.0995(2) 0.1969(2) 0.37416(15) 0.0447(6) Uani 1 1 d . . . H14A H 0.1116 0.2658 0.3403 0.054 Uiso 1 1 calc R . . H14B H 0.0337 0.1486 0.3522 0.054 Uiso 1 1 calc R . . C21 C 0.1244(3) -0.0714(2) 0.34825(16) 0.0496(6) Uani 1 1 d . . . H21A H 0.0446 -0.0348 0.3394 0.060 Uiso 1 1 calc R . . H21B H 0.1296 -0.0944 0.4037 0.060 Uiso 1 1 calc R . . C22 C 0.1374(3) -0.1811(3) 0.29590(18) 0.0601(8) Uani 1 1 d . . . H22A H 0.2139 -0.2217 0.3083 0.072 Uiso 1 1 calc R . . H22B H 0.0700 -0.2356 0.3063 0.072 Uiso 1 1 calc R . . C23 C 0.1367(3) -0.1464(2) 0.21024(18) 0.0531(7) Uani 1 1 d . . . H23A H 0.0577 -0.1115 0.1969 0.064 Uiso 1 1 calc R . . H23B H 0.1479 -0.2169 0.1776 0.064 Uiso 1 1 calc R . . C24 C 0.2375(2) -0.0582(2) 0.19267(15) 0.0426(6) Uani 1 1 d . . . H24A H 0.2340 -0.0369 0.1368 0.051 Uiso 1 1 calc R . . H24B H 0.3165 -0.0960 0.2023 0.051 Uiso 1 1 calc R . . C31 C 0.4739(2) 0.09007(19) 0.23073(12) 0.0316(5) Uani 1 1 d . . . C32 C 0.5259(2) 0.02435(19) 0.17114(13) 0.0347(5) Uani 1 1 d . . . F32 F 0.46484(13) 0.00644(13) 0.10289(8) 0.0458(3) Uani 1 1 d . . . C33 C 0.6397(2) -0.0265(2) 0.17505(15) 0.0394(6) Uani 1 1 d . . . F33 F 0.68189(14) -0.09396(13) 0.11575(9) 0.0540(4) Uani 1 1 d . . . C34 C 0.7103(2) -0.0081(2) 0.24095(17) 0.0431(6) Uani 1 1 d . . . F34 F 0.82260(13) -0.05550(15) 0.24565(11) 0.0617(5) Uani 1 1 d . . . C35 C 0.6648(2) 0.0576(2) 0.30141(15) 0.0409(6) Uani 1 1 d . . . F35 F 0.73301(14) 0.07560(14) 0.36629(10) 0.0569(4) Uani 1 1 d . . . C36 C 0.5490(2) 0.1037(2) 0.29577(13) 0.0356(5) Uani 1 1 d . . . F36 F 0.50867(13) 0.16688(13) 0.35886(8) 0.0479(4) Uani 1 1 d . . . C41 C 0.3305(2) 0.22532(19) 0.14128(13) 0.0343(5) Uani 1 1 d . . . C42 C 0.2401(2) 0.2237(2) 0.08395(16) 0.0461(6) Uani 1 1 d . . . F42 F 0.13982(14) 0.15522(18) 0.09353(10) 0.0715(5) Uani 1 1 d . . . C43 C 0.2442(3) 0.2887(3) 0.01522(17) 0.0537(7) Uani 1 1 d . . . F43 F 0.15301(19) 0.2823(2) -0.03748(12) 0.0923(7) Uani 1 1 d . . . C44 C 0.3403(3) 0.3622(2) 0.00038(15) 0.0478(6) Uani 1 1 d . . . F44 F 0.34629(18) 0.42530(16) -0.06595(10) 0.0712(5) Uani 1 1 d . . . C45 C 0.4303(2) 0.3709(2) 0.05596(15) 0.0400(6) Uani 1 1 d . . . F45 F 0.52258(15) 0.44644(13) 0.04418(9) 0.0572(4) Uani 1 1 d . . . C46 C 0.4233(2) 0.30397(19) 0.12325(13) 0.0354(5) Uani 1 1 d . . . F46 F 0.51624(12) 0.31931(12) 0.17507(8) 0.0453(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 B 0.0298(13) 0.0364(13) 0.0309(12) -0.0094(10) -0.0002(10) -0.0006(11) N 0.0330(10) 0.0415(10) 0.0331(10) -0.0017(8) 0.0034(8) 0.0036(8) C1 0.0339(12) 0.0367(11) 0.0398(13) -0.0037(10) 0.0026(10) 0.0045(10) C2 0.0268(11) 0.0397(12) 0.0353(12) -0.0041(10) -0.0008(9) 0.0003(10) C11 0.0487(15) 0.0593(15) 0.0338(12) -0.0024(12) -0.0015(11) 0.0137(13) C12 0.0723(19) 0.0492(15) 0.0346(13) -0.0004(12) 0.0078(13) 0.0083(14) C13 0.069(2) 0.100(3) 0.0590(19) -0.0055(18) 0.0069(16) 0.047(2) C14 0.0367(13) 0.0501(14) 0.0473(14) 0.0016(12) 0.0001(11) 0.0120(12) C21 0.0473(15) 0.0509(14) 0.0507(15) 0.0024(13) 0.0085(12) -0.0065(13) C22 0.0555(17) 0.0477(15) 0.077(2) -0.0013(15) 0.0117(15) -0.0185(14) C23 0.0432(15) 0.0493(14) 0.0669(18) -0.0202(14) 0.0017(13) -0.0140(13) C24 0.0359(13) 0.0466(13) 0.0452(14) -0.0114(11) 0.0016(11) -0.0079(11) C31 0.0308(11) 0.0299(10) 0.0342(11) 0.0003(9) -0.0006(9) -0.0050(9) C32 0.0356(13) 0.0350(11) 0.0334(12) -0.0020(10) 0.0008(10) -0.0042(10) F32 0.0450(8) 0.0572(8) 0.0353(7) -0.0115(6) -0.0004(6) 0.0017(7) C33 0.0400(14) 0.0326(11) 0.0457(14) -0.0017(10) 0.0099(11) -0.0003(10) F33 0.0514(9) 0.0516(8) 0.0589(9) -0.0075(8) 0.0176(7) 0.0079(7) C34 0.0283(12) 0.0374(12) 0.0636(17) 0.0040(12) 0.0006(11) 0.0014(10) F34 0.0318(8) 0.0624(10) 0.0909(12) 0.0001(9) -0.0027(8) 0.0116(7) C35 0.0381(13) 0.0372(12) 0.0474(14) 0.0022(11) -0.0121(11) -0.0059(11) F35 0.0476(9) 0.0596(9) 0.0635(10) -0.0027(8) -0.0229(8) -0.0020(8) C36 0.0374(13) 0.0333(11) 0.0362(12) -0.0024(10) -0.0017(10) -0.0024(10) F36 0.0500(8) 0.0544(8) 0.0395(7) -0.0148(6) -0.0076(6) 0.0035(7) C41 0.0303(11) 0.0354(11) 0.0372(12) -0.0062(10) -0.0009(10) 0.0031(9) C42 0.0355(13) 0.0534(14) 0.0494(15) 0.0049(12) -0.0098(11) -0.0072(12) F42 0.0472(9) 0.0996(13) 0.0677(11) 0.0281(10) -0.0232(8) -0.0299(10) C43 0.0472(15) 0.0617(17) 0.0522(16) 0.0117(13) -0.0193(13) -0.0047(14) F43 0.0783(13) 0.1208(17) 0.0780(13) 0.0439(12) -0.0472(11) -0.0347(12) C44 0.0563(16) 0.0460(14) 0.0411(14) 0.0096(12) -0.0084(12) 0.0009(13) F44 0.0833(12) 0.0726(11) 0.0576(10) 0.0289(9) -0.0169(9) -0.0088(10) C45 0.0399(14) 0.0340(12) 0.0462(14) 0.0002(11) 0.0002(11) 0.0002(10) F45 0.0592(10) 0.0534(9) 0.0591(9) 0.0135(7) -0.0027(8) -0.0192(8) C46 0.0345(12) 0.0353(11) 0.0363(12) -0.0058(10) -0.0056(10) 0.0047(10) F46 0.0407(7) 0.0487(8) 0.0465(8) 0.0046(6) -0.0110(6) -0.0115(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 B C41 1.641(3) . ? B C31 1.649(3) . ? B C2 1.652(3) . ? B H0 0.9900 . ? N C11 1.503(3) . ? N C14 1.511(3) . ? N C1 1.520(3) . ? N H0A 0.9200 . ? C1 C21 1.525(3) . ? C1 C2 1.536(3) . ? C1 H1 0.9900 . ? C2 C24 1.539(3) . ? C2 H2 0.9900 . ? C11 C12 1.498(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C12 C13 1.502(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C13 C14 1.510(4) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C21 C22 1.536(4) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C22 C23 1.508(4) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C23 C24 1.521(3) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C31 C32 1.381(3) . ? C31 C36 1.387(3) . ? C32 F32 1.355(3) . ? C32 C33 1.377(3) . ? C33 F33 1.348(3) . ? C33 C34 1.378(4) . ? C34 F34 1.347(3) . ? C34 C35 1.364(4) . ? C35 F35 1.348(3) . ? C35 C36 1.377(3) . ? C36 F36 1.364(3) . ? C41 C46 1.387(3) . ? C41 C42 1.391(3) . ? C42 F42 1.356(3) . ? C42 C43 1.381(4) . ? C43 F43 1.344(3) . ? C43 C44 1.368(4) . ? C44 F44 1.337(3) . ? C44 C45 1.370(4) . ? C45 F45 1.341(3) . ? C45 C46 1.375(3) . ? C46 F46 1.359(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 C41 B C31 108.59(18) . . ? C41 B C2 117.48(18) . . ? C31 B C2 110.98(18) . . ? C41 B H0 106.4 . . ? C31 B H0 106.4 . . ? C2 B H0 106.4 . . ? C11 N C14 106.56(18) . . ? C11 N C1 116.63(18) . . ? C14 N C1 116.62(18) . . ? C11 N H0A 105.3 . . ? C14 N H0A 105.3 . . ? C1 N H0A 105.3 . . ? N C1 C21 111.25(19) . . ? N C1 C2 109.03(18) . . ? C21 C1 C2 114.2(2) . . ? N C1 H1 107.3 . . ? C21 C1 H1 107.3 . . ? C2 C1 H1 107.3 . . ? C1 C2 C24 107.16(19) . . ? C1 C2 B 112.81(18) . . ? C24 C2 B 114.18(18) . . ? C1 C2 H2 107.5 . . ? C24 C2 H2 107.5 . . ? B C2 H2 107.5 . . ? C12 C11 N 104.0(2) . . ? C12 C11 H11A 110.9 . . ? N C11 H11A 110.9 . . ? C12 C11 H11B 110.9 . . ? N C11 H11B 110.9 . . ? H11A C11 H11B 109.0 . . ? C11 C12 C13 103.1(2) . . ? C11 C12 H12A 111.1 . . ? C13 C12 H12A 111.1 . . ? C11 C12 H12B 111.1 . . ? C13 C12 H12B 111.1 . . ? H12A C12 H12B 109.1 . . ? C12 C13 C14 106.2(2) . . ? C12 C13 H13A 110.5 . . ? C14 C13 H13A 110.5 . . ? C12 C13 H13B 110.5 . . ? C14 C13 H13B 110.5 . . ? H13A C13 H13B 108.7 . . ? C13 C14 N 105.4(2) . . ? C13 C14 H14A 110.7 . . ? N C14 H14A 110.7 . . ? C13 C14 H14B 110.7 . . ? N C14 H14B 110.7 . . ? H14A C14 H14B 108.8 . . ? C1 C21 C22 109.9(2) . . ? C1 C21 H21A 109.7 . . ? C22 C21 H21A 109.7 . . ? C1 C21 H21B 109.7 . . ? C22 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? C23 C22 C21 110.4(2) . . ? C23 C22 H22A 109.6 . . ? C21 C22 H22A 109.6 . . ? C23 C22 H22B 109.6 . . ? C21 C22 H22B 109.6 . . ? H22A C22 H22B 108.1 . . ? C22 C23 C24 110.9(2) . . ? C22 C23 H23A 109.5 . . ? C24 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? C24 C23 H23B 109.5 . . ? H23A C23 H23B 108.0 . . ? C23 C24 C2 113.4(2) . . ? C23 C24 H24A 108.9 . . ? C2 C24 H24A 108.9 . . ? C23 C24 H24B 108.9 . . ? C2 C24 H24B 108.9 . . ? H24A C24 H24B 107.7 . . ? C32 C31 C36 113.5(2) . . ? C32 C31 B 123.60(19) . . ? C36 C31 B 122.83(19) . . ? F32 C32 C33 115.3(2) . . ? F32 C32 C31 120.3(2) . . ? C33 C32 C31 124.4(2) . . ? F33 C33 C32 120.9(2) . . ? F33 C33 C34 120.0(2) . . ? C32 C33 C34 119.1(2) . . ? F34 C34 C35 120.5(2) . . ? F34 C34 C33 120.2(2) . . ? C35 C34 C33 119.3(2) . . ? F35 C35 C34 119.7(2) . . ? F35 C35 C36 120.8(2) . . ? C34 C35 C36 119.5(2) . . ? F36 C36 C35 116.3(2) . . ? F36 C36 C31 119.5(2) . . ? C35 C36 C31 124.2(2) . . ? C46 C41 C42 112.1(2) . . ? C46 C41 B 118.62(19) . . ? C42 C41 B 129.2(2) . . ? F42 C42 C43 115.7(2) . . ? F42 C42 C41 120.1(2) . . ? C43 C42 C41 124.2(2) . . ? F43 C43 C44 118.9(2) . . ? F43 C43 C42 120.7(3) . . ? C44 C43 C42 120.4(2) . . ? F44 C44 C43 121.3(2) . . ? F44 C44 C45 120.5(3) . . ? C43 C44 C45 118.2(2) . . ? F45 C45 C44 119.2(2) . . ? F45 C45 C46 121.3(2) . . ? C44 C45 C46 119.5(2) . . ? F46 C46 C45 115.2(2) . . ? F46 C46 C41 119.3(2) . . ? C45 C46 C41 125.4(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N C1 C21 66.9(3) . . . . ? C14 N C1 C21 -60.5(3) . . . . ? C11 N C1 C2 -166.2(2) . . . . ? C14 N C1 C2 66.3(2) . . . . ? N C1 C2 C24 -179.47(18) . . . . ? C21 C1 C2 C24 -54.3(3) . . . . ? N C1 C2 B 54.0(2) . . . . ? C21 C1 C2 B 179.17(19) . . . . ? C41 B C2 C1 -164.23(19) . . . . ? C31 B C2 C1 70.0(2) . . . . ? C41 B C2 C24 73.1(3) . . . . ? C31 B C2 C24 -52.7(2) . . . . ? C14 N C11 C12 -29.1(3) . . . . ? C1 N C11 C12 -161.3(2) . . . . ? N C11 C12 C13 38.4(3) . . . . ? C11 C12 C13 C14 -33.7(3) . . . . ? C12 C13 C14 N 15.8(3) . . . . ? C11 N C14 C13 8.2(3) . . . . ? C1 N C14 C13 140.4(3) . . . . ? N C1 C21 C22 -179.4(2) . . . . ? C2 C1 C21 C22 56.7(3) . . . . ? C1 C21 C22 C23 -56.1(3) . . . . ? C21 C22 C23 C24 57.2(3) . . . . ? C22 C23 C24 C2 -57.9(3) . . . . ? C1 C2 C24 C23 54.3(3) . . . . ? B C2 C24 C23 179.9(2) . . . . ? C41 B C31 C32 -49.6(3) . . . . ? C2 B C31 C32 81.0(3) . . . . ? C41 B C31 C36 127.6(2) . . . . ? C2 B C31 C36 -101.8(2) . . . . ? C36 C31 C32 F32 -178.06(19) . . . . ? B C31 C32 F32 -0.6(3) . . . . ? C36 C31 C32 C33 1.6(3) . . . . ? B C31 C32 C33 179.1(2) . . . . ? F32 C32 C33 F33 -3.4(3) . . . . ? C31 C32 C33 F33 176.9(2) . . . . ? F32 C32 C33 C34 177.1(2) . . . . ? C31 C32 C33 C34 -2.6(3) . . . . ? F33 C33 C34 F34 1.4(3) . . . . ? C32 C33 C34 F34 -179.0(2) . . . . ? F33 C33 C34 C35 -178.1(2) . . . . ? C32 C33 C34 C35 1.5(4) . . . . ? F34 C34 C35 F35 0.2(4) . . . . ? C33 C34 C35 F35 179.7(2) . . . . ? F34 C34 C35 C36 -179.0(2) . . . . ? C33 C34 C35 C36 0.5(4) . . . . ? F35 C35 C36 F36 -0.2(3) . . . . ? C34 C35 C36 F36 179.0(2) . . . . ? F35 C35 C36 C31 179.3(2) . . . . ? C34 C35 C36 C31 -1.5(4) . . . . ? C32 C31 C36 F36 179.93(19) . . . . ? B C31 C36 F36 2.5(3) . . . . ? C32 C31 C36 C35 0.5(3) . . . . ? B C31 C36 C35 -177.0(2) . . . . ? C31 B C41 C46 -50.6(3) . . . . ? C2 B C41 C46 -177.56(19) . . . . ? C31 B C41 C42 131.2(2) . . . . ? C2 B C41 C42 4.3(3) . . . . ? C46 C41 C42 F42 -177.4(2) . . . . ? B C41 C42 F42 0.9(4) . . . . ? C46 C41 C42 C43 2.7(4) . . . . ? B C41 C42 C43 -179.0(3) . . . . ? F42 C42 C43 F43 0.1(4) . . . . ? C41 C42 C43 F43 180.0(3) . . . . ? F42 C42 C43 C44 178.9(3) . . . . ? C41 C42 C43 C44 -1.2(5) . . . . ? F43 C43 C44 F44 -1.5(5) . . . . ? C42 C43 C44 F44 179.7(3) . . . . ? F43 C43 C44 C45 177.6(3) . . . . ? C42 C43 C44 C45 -1.2(4) . . . . ? F44 C44 C45 F45 2.1(4) . . . . ? C43 C44 C45 F45 -177.0(2) . . . . ? F44 C44 C45 C46 -179.1(2) . . . . ? C43 C44 C45 C46 1.8(4) . . . . ? F45 C45 C46 F46 -0.8(3) . . . . ? C44 C45 C46 F46 -179.5(2) . . . . ? F45 C45 C46 C41 178.8(2) . . . . ? C44 C45 C46 C41 0.0(4) . . . . ? C42 C41 C46 F46 177.4(2) . . . . ? B C41 C46 F46 -1.1(3) . . . . ? C42 C41 C46 C45 -2.1(3) . . . . ? B C41 C46 C45 179.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 66.92 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.172 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.034 # Attachment '- 14a.cif' data_erk5485 _database_code_depnum_ccdc_archive 'CCDC 815790' #TrackingRef '- 14a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H26 B F10 N O' _chemical_formula_weight 617.33 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' O O 0.0492 0.0322 '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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4280(4) _cell_length_b 11.0909(6) _cell_length_c 14.6744(8) _cell_angle_alpha 108.637(3) _cell_angle_beta 96.263(3) _cell_angle_gamma 105.831(2) _cell_volume 1366.01(12) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3785 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 1.202 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8691 _exptl_absorpt_correction_T_max 0.9423 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22561 _diffrn_reflns_av_R_equivalents 0.044 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.45 _diffrn_reflns_theta_max 67.51 _reflns_number_total 4675 _reflns_number_gt 4030 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0476P)^2^+0.8881P] 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 4675 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0516 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1137 _refine_ls_wR_factor_gt 0.1077 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 N N 0.70013(18) 0.04189(16) 0.24091(12) 0.0336(4) Uani 1 1 d . . . B B 0.5515(2) 0.2698(2) 0.22649(15) 0.0295(4) Uani 1 1 d . . . C1 C 0.7754(2) 0.1522(2) 0.20682(15) 0.0339(4) Uani 1 1 d . . . H1 H 0.8493 0.2250 0.2644 0.041 Uiso 1 1 calc R . . C2 C 0.6717(2) 0.21567(19) 0.16387(14) 0.0312(4) Uani 1 1 d . . . H2 H 0.6113 0.1472 0.0996 0.037 Uiso 1 1 calc R . . O3 O 0.43497(14) 0.15267(13) 0.22946(10) 0.0338(3) Uani 1 1 d . . . C4 C 0.3161(2) 0.1722(2) 0.27748(16) 0.0396(5) Uani 1 1 d . . . H4A H 0.2522 0.2063 0.2419 0.048 Uiso 1 1 calc R . . H4B H 0.3576 0.2383 0.3447 0.048 Uiso 1 1 calc R . . C5 C 0.2242(2) 0.0397(2) 0.28013(16) 0.0370(5) Uani 1 1 d . . . C6 C 0.2244(3) 0.0169(2) 0.36741(19) 0.0520(6) Uani 1 1 d . . . H6 H 0.2797 0.0865 0.4271 0.062 Uiso 1 1 calc R . . C7 C 0.1439(4) -0.1073(3) 0.3678(2) 0.0675(8) Uani 1 1 d . . . H7 H 0.1449 -0.1213 0.4277 0.081 Uiso 1 1 calc R . . C8 C 0.0633(3) -0.2096(3) 0.2820(2) 0.0658(8) Uani 1 1 d . . . H8 H 0.0094 -0.2940 0.2828 0.079 Uiso 1 1 calc R . . C9 C 0.0607(3) -0.1892(2) 0.1944(2) 0.0549(6) Uani 1 1 d . . . H9 H 0.0049 -0.2594 0.1351 0.066 Uiso 1 1 calc R . . C10 C 0.1409(2) -0.0646(2) 0.19385(18) 0.0451(5) Uani 1 1 d . . . H10 H 0.1386 -0.0507 0.1338 0.054 Uiso 1 1 calc R . . C11 C 0.7971(2) 0.0294(2) 0.32203(17) 0.0440(5) Uani 1 1 d . . . H11A H 0.8082 0.1039 0.3834 0.053 Uiso 1 1 calc R . . H11B H 0.8976 0.0374 0.3078 0.053 Uiso 1 1 calc R . . C12 C 0.7348(3) -0.1013(3) 0.3365(2) 0.0671(7) Uani 1 1 d . . . H12A H 0.7581 -0.1720 0.2866 0.080 Uiso 1 1 calc R . . H12B H 0.7853 -0.0931 0.4012 0.080 Uiso 1 1 calc R . . C13 C 0.5725(3) -0.1418(3) 0.3298(2) 0.0728(8) Uani 1 1 d . . . H13A H 0.5496 -0.0771 0.3846 0.087 Uiso 1 1 calc R . . H13B H 0.5380 -0.2303 0.3355 0.087 Uiso 1 1 calc R . . C14 C 0.4879(2) -0.1485(2) 0.23244(18) 0.0463(5) Uani 1 1 d . . . H14A H 0.4761 -0.2350 0.1811 0.056 Uiso 1 1 calc R . . H14B H 0.3868 -0.1448 0.2392 0.056 Uiso 1 1 calc R . . C15 C 0.5657(2) -0.03821(19) 0.20114(15) 0.0359(4) Uani 1 1 d . . . H15 H 0.5125 -0.0263 0.1484 0.043 Uiso 1 1 calc R . . C21 C 0.8651(2) 0.0947(2) 0.13282(17) 0.0453(5) Uani 1 1 d . . . H21A H 0.9273 0.0527 0.1616 0.054 Uiso 1 1 calc R . . H21B H 0.7948 0.0250 0.0734 0.054 Uiso 1 1 calc R . . C22 C 0.9659(3) 0.2040(3) 0.10510(19) 0.0508(6) Uani 1 1 d . . . H22A H 1.0150 0.1634 0.0536 0.061 Uiso 1 1 calc R . . H22B H 1.0449 0.2674 0.1627 0.061 Uiso 1 1 calc R . . C23 C 0.8744(3) 0.2794(3) 0.06815(18) 0.0477(5) Uani 1 1 d . . . H23A H 0.9427 0.3560 0.0581 0.057 Uiso 1 1 calc R . . H23B H 0.8065 0.2194 0.0047 0.057 Uiso 1 1 calc R . . C24 C 0.7825(2) 0.3295(2) 0.14169(16) 0.0381(5) Uani 1 1 d . . . H24A H 0.7247 0.3773 0.1160 0.046 Uiso 1 1 calc R . . H24B H 0.8517 0.3941 0.2034 0.046 Uiso 1 1 calc R . . C31 C 0.6502(2) 0.37564(19) 0.33948(14) 0.0336(4) Uani 1 1 d . . . C32 C 0.6720(2) 0.3329(2) 0.41754(15) 0.0386(5) Uani 1 1 d . . . F32 F 0.60245(16) 0.20322(12) 0.40768(9) 0.0514(3) Uani 1 1 d . . . C33 C 0.7631(3) 0.4135(3) 0.50905(15) 0.0472(6) Uani 1 1 d . . . F33 F 0.78084(19) 0.36176(17) 0.57903(10) 0.0699(4) Uani 1 1 d . . . C34 C 0.8360(3) 0.5465(3) 0.52762(16) 0.0519(6) Uani 1 1 d . . . F34 F 0.92364(18) 0.62778(18) 0.61675(10) 0.0797(5) Uani 1 1 d . . . C35 C 0.8192(2) 0.5958(2) 0.45388(17) 0.0478(5) Uani 1 1 d . . . F35 F 0.89057(17) 0.72692(14) 0.47135(11) 0.0693(4) Uani 1 1 d . . . C36 C 0.7294(2) 0.5110(2) 0.36337(15) 0.0388(5) Uani 1 1 d . . . F36 F 0.71987(14) 0.56883(12) 0.29515(9) 0.0483(3) Uani 1 1 d . . . C41 C 0.4600(2) 0.34597(18) 0.16917(14) 0.0319(4) Uani 1 1 d . . . C42 C 0.3950(2) 0.43980(19) 0.21788(14) 0.0341(4) Uani 1 1 d . . . F42 F 0.41254(14) 0.48142(12) 0.31695(8) 0.0443(3) Uani 1 1 d . . . C43 C 0.3083(2) 0.4951(2) 0.17229(16) 0.0382(5) Uani 1 1 d . . . F43 F 0.24689(15) 0.58285(13) 0.22499(10) 0.0532(3) Uani 1 1 d . . . C44 C 0.2839(2) 0.4605(2) 0.07243(17) 0.0420(5) Uani 1 1 d . . . F44 F 0.20145(16) 0.51398(15) 0.02682(11) 0.0617(4) Uani 1 1 d . . . C45 C 0.3423(2) 0.3664(2) 0.01947(15) 0.0432(5) Uani 1 1 d . . . F45 F 0.31943(17) 0.32965(17) -0.07933(10) 0.0657(4) Uani 1 1 d . . . C46 C 0.4250(2) 0.3115(2) 0.06774(15) 0.0375(5) Uani 1 1 d . . . F46 F 0.47240(16) 0.21671(14) 0.00663(9) 0.0545(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 N 0.0343(9) 0.0337(9) 0.0389(9) 0.0176(7) 0.0097(7) 0.0148(7) B 0.0326(11) 0.0280(11) 0.0298(11) 0.0122(9) 0.0067(9) 0.0107(9) C1 0.0309(10) 0.0350(10) 0.0396(11) 0.0189(9) 0.0078(8) 0.0099(8) C2 0.0305(9) 0.0317(10) 0.0328(10) 0.0144(8) 0.0058(8) 0.0097(8) O3 0.0330(7) 0.0327(7) 0.0401(7) 0.0157(6) 0.0136(6) 0.0124(6) C4 0.0376(11) 0.0394(11) 0.0513(12) 0.0216(10) 0.0188(9) 0.0178(9) C5 0.0322(10) 0.0381(11) 0.0508(12) 0.0214(10) 0.0180(9) 0.0174(9) C6 0.0610(15) 0.0509(14) 0.0514(14) 0.0248(11) 0.0211(11) 0.0185(12) C7 0.086(2) 0.0631(17) 0.0748(19) 0.0443(16) 0.0407(16) 0.0259(16) C8 0.0594(16) 0.0473(15) 0.106(2) 0.0393(16) 0.0457(16) 0.0176(13) C9 0.0356(12) 0.0431(13) 0.0759(17) 0.0108(12) 0.0145(11) 0.0095(10) C10 0.0357(11) 0.0505(13) 0.0540(14) 0.0218(11) 0.0127(10) 0.0173(10) C11 0.0415(12) 0.0531(13) 0.0474(12) 0.0286(11) 0.0066(9) 0.0198(10) C12 0.0682(17) 0.0683(17) 0.0753(18) 0.0487(15) 0.0031(14) 0.0169(14) C13 0.0694(18) 0.0755(19) 0.095(2) 0.0617(18) 0.0211(16) 0.0198(15) C14 0.0427(12) 0.0360(11) 0.0663(15) 0.0241(11) 0.0184(11) 0.0133(10) C15 0.0369(11) 0.0312(10) 0.0429(11) 0.0129(9) 0.0114(9) 0.0156(9) C21 0.0420(12) 0.0546(13) 0.0561(14) 0.0308(11) 0.0186(10) 0.0261(10) C22 0.0411(12) 0.0671(15) 0.0645(15) 0.0389(13) 0.0261(11) 0.0257(11) C23 0.0446(12) 0.0621(14) 0.0551(14) 0.0372(12) 0.0229(10) 0.0229(11) C24 0.0365(11) 0.0415(11) 0.0449(12) 0.0252(10) 0.0124(9) 0.0133(9) C31 0.0339(10) 0.0361(11) 0.0329(10) 0.0125(8) 0.0082(8) 0.0145(8) C32 0.0463(12) 0.0397(11) 0.0351(11) 0.0141(9) 0.0103(9) 0.0212(9) F32 0.0771(9) 0.0434(7) 0.0426(7) 0.0232(6) 0.0112(6) 0.0252(7) C33 0.0534(13) 0.0659(16) 0.0298(11) 0.0177(10) 0.0076(10) 0.0315(12) F33 0.0949(11) 0.0916(11) 0.0361(7) 0.0277(7) 0.0062(7) 0.0483(10) C34 0.0434(12) 0.0620(16) 0.0336(12) 0.0004(11) -0.0016(9) 0.0155(11) F34 0.0693(10) 0.0926(12) 0.0407(8) -0.0011(8) -0.0124(7) 0.0099(9) C35 0.0397(12) 0.0414(12) 0.0457(13) 0.0044(10) 0.0049(10) 0.0031(10) F35 0.0657(9) 0.0450(8) 0.0646(9) 0.0029(7) 0.0039(7) -0.0077(7) C36 0.0370(11) 0.0407(11) 0.0386(11) 0.0144(9) 0.0084(9) 0.0124(9) F36 0.0549(7) 0.0371(7) 0.0499(7) 0.0212(6) 0.0077(6) 0.0052(6) C41 0.0309(10) 0.0295(10) 0.0355(10) 0.0137(8) 0.0059(8) 0.0085(8) C42 0.0356(10) 0.0321(10) 0.0370(11) 0.0168(8) 0.0086(8) 0.0097(8) F42 0.0571(7) 0.0470(7) 0.0372(6) 0.0159(5) 0.0142(5) 0.0280(6) C43 0.0359(10) 0.0355(11) 0.0525(13) 0.0232(10) 0.0149(9) 0.0152(9) F43 0.0606(8) 0.0531(8) 0.0661(9) 0.0293(7) 0.0237(7) 0.0370(7) C44 0.0354(11) 0.0499(13) 0.0540(13) 0.0337(11) 0.0089(9) 0.0170(10) F44 0.0617(8) 0.0809(10) 0.0720(9) 0.0514(8) 0.0145(7) 0.0407(8) C45 0.0423(12) 0.0545(13) 0.0368(11) 0.0238(10) 0.0053(9) 0.0149(10) F45 0.0736(10) 0.0977(11) 0.0378(7) 0.0292(7) 0.0054(7) 0.0436(9) C46 0.0369(11) 0.0420(11) 0.0358(11) 0.0134(9) 0.0077(8) 0.0170(9) F46 0.0670(9) 0.0658(9) 0.0331(6) 0.0089(6) 0.0036(6) 0.0390(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N C15 1.277(3) . ? N C11 1.486(3) . ? N C1 1.499(2) . ? B O3 1.471(2) . ? B C2 1.654(3) . ? B C31 1.678(3) . ? B C41 1.691(3) . ? C1 C21 1.533(3) . ? C1 C2 1.541(3) . ? C1 H1 0.9900 . ? C2 C24 1.552(3) . ? C2 H2 0.9900 . ? O3 C4 1.416(2) . ? C4 C5 1.503(3) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C5 C10 1.382(3) . ? C5 C6 1.383(3) . ? C6 C7 1.381(4) . ? C6 H6 0.9400 . ? C7 C8 1.363(4) . ? C7 H7 0.9400 . ? C8 C9 1.374(4) . ? C8 H8 0.9400 . ? C9 C10 1.386(3) . ? C9 H9 0.9400 . ? C10 H10 0.9400 . ? C11 C12 1.500(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C12 C13 1.455(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C13 C14 1.528(4) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C14 C15 1.480(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C15 H15 0.9400 . ? C21 C22 1.520(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C22 C23 1.522(3) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C23 C24 1.520(3) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C31 C32 1.389(3) . ? C31 C36 1.389(3) . ? C32 F32 1.360(2) . ? C32 C33 1.379(3) . ? C33 F33 1.343(3) . ? C33 C34 1.368(4) . ? C34 F34 1.346(3) . ? C34 C35 1.372(4) . ? C35 F35 1.351(3) . ? C35 C36 1.374(3) . ? C36 F36 1.358(2) . ? C41 C46 1.390(3) . ? C41 C42 1.392(3) . ? C42 F42 1.353(2) . ? C42 C43 1.382(3) . ? C43 F43 1.343(2) . ? C43 C44 1.366(3) . ? C44 F44 1.340(2) . ? C44 C45 1.372(3) . ? C45 F45 1.349(2) . ? C45 C46 1.377(3) . ? C46 F46 1.360(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 C15 N C11 122.59(17) . . ? C15 N C1 122.84(16) . . ? C11 N C1 114.52(15) . . ? O3 B C2 108.51(15) . . ? O3 B C31 112.06(15) . . ? C2 B C31 107.47(15) . . ? O3 B C41 106.24(15) . . ? C2 B C41 111.19(15) . . ? C31 B C41 111.38(15) . . ? N C1 C21 106.63(15) . . ? N C1 C2 116.41(15) . . ? C21 C1 C2 111.47(16) . . ? N C1 H1 107.3 . . ? C21 C1 H1 107.3 . . ? C2 C1 H1 107.3 . . ? C1 C2 C24 103.91(15) . . ? C1 C2 B 119.73(15) . . ? C24 C2 B 111.91(15) . . ? C1 C2 H2 106.9 . . ? C24 C2 H2 106.9 . . ? B C2 H2 106.9 . . ? C4 O3 B 119.56(14) . . ? O3 C4 C5 108.69(15) . . ? O3 C4 H4A 110.0 . . ? C5 C4 H4A 110.0 . . ? O3 C4 H4B 110.0 . . ? C5 C4 H4B 110.0 . . ? H4A C4 H4B 108.3 . . ? C10 C5 C6 118.2(2) . . ? C10 C5 C4 120.23(19) . . ? C6 C5 C4 121.5(2) . . ? C7 C6 C5 120.6(2) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C8 C7 C6 120.5(3) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 119.9(2) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C8 C9 C10 119.6(2) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C5 C10 C9 121.1(2) . . ? C5 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? N C11 C12 113.02(19) . . ? N C11 H11A 109.0 . . ? C12 C11 H11A 109.0 . . ? N C11 H11B 109.0 . . ? C12 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C13 C12 C11 113.3(2) . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12B 108.9 . . ? C11 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C12 C13 C14 111.4(2) . . ? C12 C13 H13A 109.4 . . ? C14 C13 H13A 109.4 . . ? C12 C13 H13B 109.4 . . ? C14 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? C15 C14 C13 113.00(19) . . ? C15 C14 H14A 109.0 . . ? C13 C14 H14A 109.0 . . ? C15 C14 H14B 109.0 . . ? C13 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? N C15 C14 124.38(19) . . ? N C15 H15 117.8 . . ? C14 C15 H15 117.8 . . ? C22 C21 C1 111.27(18) . . ? C22 C21 H21A 109.4 . . ? C1 C21 H21A 109.4 . . ? C22 C21 H21B 109.4 . . ? C1 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? C21 C22 C23 110.74(18) . . ? C21 C22 H22A 109.5 . . ? C23 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? C23 C22 H22B 109.5 . . ? H22A C22 H22B 108.1 . . ? C24 C23 C22 110.62(18) . . ? C24 C23 H23A 109.5 . . ? C22 C23 H23A 109.5 . . ? C24 C23 H23B 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 108.1 . . ? C23 C24 C2 113.61(17) . . ? C23 C24 H24A 108.8 . . ? C2 C24 H24A 108.8 . . ? C23 C24 H24B 108.8 . . ? C2 C24 H24B 108.8 . . ? H24A C24 H24B 107.7 . . ? C32 C31 C36 112.62(18) . . ? C32 C31 B 122.63(17) . . ? C36 C31 B 124.51(17) . . ? F32 C32 C33 114.51(18) . . ? F32 C32 C31 120.78(18) . . ? C33 C32 C31 124.7(2) . . ? F33 C33 C34 120.3(2) . . ? F33 C33 C32 120.3(2) . . ? C34 C33 C32 119.3(2) . . ? F34 C34 C33 120.5(2) . . ? F34 C34 C35 120.4(2) . . ? C33 C34 C35 119.1(2) . . ? F35 C35 C34 119.6(2) . . ? F35 C35 C36 121.0(2) . . ? C34 C35 C36 119.4(2) . . ? F36 C36 C35 115.16(19) . . ? F36 C36 C31 120.05(18) . . ? C35 C36 C31 124.8(2) . . ? C46 C41 C42 111.91(17) . . ? C46 C41 B 124.42(16) . . ? C42 C41 B 123.26(16) . . ? F42 C42 C43 115.13(17) . . ? F42 C42 C41 120.08(17) . . ? C43 C42 C41 124.79(18) . . ? F43 C43 C44 119.23(18) . . ? F43 C43 C42 120.79(19) . . ? C44 C43 C42 119.99(19) . . ? F44 C44 C43 121.0(2) . . ? F44 C44 C45 120.7(2) . . ? C43 C44 C45 118.33(18) . . ? F45 C45 C44 119.72(19) . . ? F45 C45 C46 120.6(2) . . ? C44 C45 C46 119.70(19) . . ? F46 C46 C45 113.85(18) . . ? F46 C46 C41 120.95(17) . . ? C45 C46 C41 125.20(19) . . ? 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 C15 N C1 C21 -93.9(2) . . . . ? C11 N C1 C21 83.6(2) . . . . ? C15 N C1 C2 31.2(3) . . . . ? C11 N C1 C2 -151.34(17) . . . . ? N C1 C2 C24 176.82(16) . . . . ? C21 C1 C2 C24 -60.6(2) . . . . ? N C1 C2 B 51.1(2) . . . . ? C21 C1 C2 B 173.67(17) . . . . ? O3 B C2 C1 -67.9(2) . . . . ? C31 B C2 C1 53.5(2) . . . . ? C41 B C2 C1 175.61(15) . . . . ? O3 B C2 C24 170.23(15) . . . . ? C31 B C2 C24 -68.41(19) . . . . ? C41 B C2 C24 53.7(2) . . . . ? C2 B O3 C4 -178.71(16) . . . . ? C31 B O3 C4 62.8(2) . . . . ? C41 B O3 C4 -59.1(2) . . . . ? B O3 C4 C5 -173.45(16) . . . . ? O3 C4 C5 C10 -66.8(2) . . . . ? O3 C4 C5 C6 111.0(2) . . . . ? C10 C5 C6 C7 0.4(3) . . . . ? C4 C5 C6 C7 -177.4(2) . . . . ? C5 C6 C7 C8 0.1(4) . . . . ? C6 C7 C8 C9 -0.4(4) . . . . ? C7 C8 C9 C10 0.2(4) . . . . ? C6 C5 C10 C9 -0.6(3) . . . . ? C4 C5 C10 C9 177.18(19) . . . . ? C8 C9 C10 C5 0.3(3) . . . . ? C15 N C11 C12 12.5(3) . . . . ? C1 N C11 C12 -164.9(2) . . . . ? N C11 C12 C13 -42.0(3) . . . . ? C11 C12 C13 C14 55.4(4) . . . . ? C12 C13 C14 C15 -39.3(3) . . . . ? C11 N C15 C14 2.5(3) . . . . ? C1 N C15 C14 179.71(18) . . . . ? C13 C14 C15 N 10.9(3) . . . . ? N C1 C21 C22 -171.15(17) . . . . ? C2 C1 C21 C22 60.8(2) . . . . ? C1 C21 C22 C23 -54.3(3) . . . . ? C21 C22 C23 C24 52.5(3) . . . . ? C22 C23 C24 C2 -58.4(3) . . . . ? C1 C2 C24 C23 60.5(2) . . . . ? B C2 C24 C23 -168.90(17) . . . . ? O3 B C31 C32 28.4(2) . . . . ? C2 B C31 C32 -90.7(2) . . . . ? C41 B C31 C32 147.27(18) . . . . ? O3 B C31 C36 -157.62(18) . . . . ? C2 B C31 C36 83.3(2) . . . . ? C41 B C31 C36 -38.8(2) . . . . ? C36 C31 C32 F32 179.64(17) . . . . ? B C31 C32 F32 -5.7(3) . . . . ? C36 C31 C32 C33 -0.7(3) . . . . ? B C31 C32 C33 173.90(19) . . . . ? F32 C32 C33 F33 1.8(3) . . . . ? C31 C32 C33 F33 -177.88(19) . . . . ? F32 C32 C33 C34 -178.61(19) . . . . ? C31 C32 C33 C34 1.7(3) . . . . ? F33 C33 C34 F34 -1.4(3) . . . . ? C32 C33 C34 F34 179.0(2) . . . . ? F33 C33 C34 C35 178.2(2) . . . . ? C32 C33 C34 C35 -1.4(3) . . . . ? F34 C34 C35 F35 -0.4(3) . . . . ? C33 C34 C35 F35 -180.0(2) . . . . ? F34 C34 C35 C36 179.8(2) . . . . ? C33 C34 C35 C36 0.2(3) . . . . ? F35 C35 C36 F36 0.3(3) . . . . ? C34 C35 C36 F36 -179.9(2) . . . . ? F35 C35 C36 C31 -179.0(2) . . . . ? C34 C35 C36 C31 0.8(3) . . . . ? C32 C31 C36 F36 -179.78(17) . . . . ? B C31 C36 F36 5.7(3) . . . . ? C32 C31 C36 C35 -0.6(3) . . . . ? B C31 C36 C35 -175.1(2) . . . . ? O3 B C41 C46 -86.6(2) . . . . ? C2 B C41 C46 31.3(2) . . . . ? C31 B C41 C46 151.13(18) . . . . ? O3 B C41 C42 85.4(2) . . . . ? C2 B C41 C42 -156.73(17) . . . . ? C31 B C41 C42 -36.9(2) . . . . ? C46 C41 C42 F42 177.60(17) . . . . ? B C41 C42 F42 4.7(3) . . . . ? C46 C41 C42 C43 -1.2(3) . . . . ? B C41 C42 C43 -174.06(18) . . . . ? F42 C42 C43 F43 -0.4(3) . . . . ? C41 C42 C43 F43 178.40(18) . . . . ? F42 C42 C43 C44 179.73(18) . . . . ? C41 C42 C43 C44 -1.4(3) . . . . ? F43 C43 C44 F44 0.9(3) . . . . ? C42 C43 C44 F44 -179.30(18) . . . . ? F43 C43 C44 C45 -177.30(18) . . . . ? C42 C43 C44 C45 2.5(3) . . . . ? F44 C44 C45 F45 1.5(3) . . . . ? C43 C44 C45 F45 179.69(19) . . . . ? F44 C44 C45 C46 -179.17(19) . . . . ? C43 C44 C45 C46 -1.0(3) . . . . ? F45 C45 C46 F46 -2.6(3) . . . . ? C44 C45 C46 F46 178.08(19) . . . . ? F45 C45 C46 C41 177.42(19) . . . . ? C44 C45 C46 C41 -1.9(3) . . . . ? C42 C41 C46 F46 -177.11(17) . . . . ? B C41 C46 F46 -4.3(3) . . . . ? C42 C41 C46 C45 2.8(3) . . . . ? B C41 C46 C45 175.62(19) . . . . ? _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 67.51 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 0.581 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.040 # Attachment '- 14b.cif' data_erk5526 _database_code_depnum_ccdc_archive 'CCDC 815791' #TrackingRef '- 14b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C43 H38 B F10 N O' _chemical_formula_weight 785.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' O O 0.0492 0.0322 '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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 20.3695(8) _cell_length_b 9.2993(7) _cell_length_c 21.5910(10) _cell_angle_alpha 90.00 _cell_angle_beta 114.314(2) _cell_angle_gamma 90.00 _cell_volume 3727.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6254 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1624 _exptl_absorpt_coefficient_mu 1.008 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8239 _exptl_absorpt_correction_T_max 0.9513 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26897 _diffrn_reflns_av_R_equivalents 0.072 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.76 _diffrn_reflns_theta_max 67.04 _reflns_number_total 6389 _reflns_number_gt 4471 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to Zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0714P)^2^+2.1401P] 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 SHELXL _refine_ls_extinction_coef 0.00107(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6389 _refine_ls_number_parameters 507 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0828 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1574 _refine_ls_wR_factor_gt 0.1336 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 N N 0.22435(12) 0.3165(2) -0.21007(11) 0.0454(6) Uani 1 1 d . . . B B 0.24774(16) 0.5032(3) -0.07711(15) 0.0379(7) Uani 1 1 d . . . C1 C 0.27616(15) 0.2708(3) -0.14075(14) 0.0458(7) Uani 1 1 d . . . H1 H 0.3239 0.3100 -0.1336 0.055 Uiso 1 1 calc R . . C2 C 0.25827(14) 0.3272(3) -0.08240(13) 0.0409(6) Uani 1 1 d . . . H2 H 0.2126 0.2811 -0.0874 0.049 Uiso 1 1 calc R . . O3 O 0.17617(9) 0.54465(18) -0.12958(9) 0.0399(4) Uani 1 1 d . . . C4 C 0.15294(14) 0.6903(3) -0.13880(13) 0.0403(6) Uani 1 1 d . . . H4 H 0.1951 0.7526 -0.1310 0.048 Uiso 1 1 calc R . . C5 C 0.09875(15) 0.7093(3) -0.21177(13) 0.0430(6) Uani 1 1 d . . . C6 C 0.03928(15) 0.6191(3) -0.23993(14) 0.0516(7) Uani 1 1 d . . . H6 H 0.0328 0.5452 -0.2133 0.062 Uiso 1 1 calc R . . C7 C -0.01043(17) 0.6362(4) -0.30634(15) 0.0597(8) Uani 1 1 d . . . H7 H -0.0502 0.5741 -0.3245 0.072 Uiso 1 1 calc R . . C8 C -0.00170(19) 0.7449(4) -0.34625(16) 0.0642(9) Uani 1 1 d . . . H8 H -0.0355 0.7569 -0.3914 0.077 Uiso 1 1 calc R . . C9 C 0.05657(19) 0.8343(4) -0.31923(16) 0.0620(9) Uani 1 1 d . . . H9 H 0.0627 0.9083 -0.3460 0.074 Uiso 1 1 calc R . . C10 C 0.10665(17) 0.8169(3) -0.25268(14) 0.0519(7) Uani 1 1 d . . . H10 H 0.1465 0.8789 -0.2350 0.062 Uiso 1 1 calc R . . C11 C 0.24788(18) 0.3638(3) -0.25293(15) 0.0557(8) Uani 1 1 d . . . H11 H 0.2981 0.3698 -0.2386 0.067 Uiso 1 1 calc R . . C12 C 0.20197(19) 0.4095(4) -0.32315(16) 0.0659(9) Uani 1 1 d . . . H12A H 0.2077 0.3408 -0.3550 0.079 Uiso 1 1 calc R . . H12B H 0.2185 0.5036 -0.3314 0.079 Uiso 1 1 calc R . . C13 C 0.12322(19) 0.4197(4) -0.33723(17) 0.0702(9) Uani 1 1 d . . . H13A H 0.1139 0.5112 -0.3199 0.084 Uiso 1 1 calc R . . H13B H 0.0941 0.4168 -0.3864 0.084 Uiso 1 1 calc R . . C14 C 0.10223(18) 0.2974(4) -0.30379(15) 0.0631(9) Uani 1 1 d . . . H14A H 0.1092 0.2062 -0.3231 0.076 Uiso 1 1 calc R . . H14B H 0.0511 0.3057 -0.3130 0.076 Uiso 1 1 calc R . . C15 C 0.14656(15) 0.2969(3) -0.22793(14) 0.0514(7) Uani 1 1 d . . . H15A H 0.1298 0.3743 -0.2072 0.062 Uiso 1 1 calc R . . H15B H 0.1393 0.2055 -0.2091 0.062 Uiso 1 1 calc R . . C21 C 0.28182(19) 0.1058(3) -0.14198(17) 0.0614(8) Uani 1 1 d . . . H21A H 0.2348 0.0633 -0.1505 0.074 Uiso 1 1 calc R . . H21B H 0.2947 0.0774 -0.1793 0.074 Uiso 1 1 calc R . . C22 C 0.3377(2) 0.0482(3) -0.07565(18) 0.0679(9) Uani 1 1 d . . . H22A H 0.3365 -0.0572 -0.0765 0.082 Uiso 1 1 calc R . . H22B H 0.3857 0.0791 -0.0703 0.082 Uiso 1 1 calc R . . C23 C 0.32369(18) 0.1014(3) -0.01604(16) 0.0583(8) Uani 1 1 d . . . H23A H 0.3629 0.0706 0.0265 0.070 Uiso 1 1 calc R . . H23B H 0.2787 0.0596 -0.0179 0.070 Uiso 1 1 calc R . . C24 C 0.31820(16) 0.2651(3) -0.01737(15) 0.0483(7) Uani 1 1 d . . . H24A H 0.3645 0.3054 -0.0126 0.058 Uiso 1 1 calc R . . H24B H 0.3096 0.2965 0.0220 0.058 Uiso 1 1 calc R . . C31 C 0.31606(14) 0.5852(3) -0.08783(13) 0.0382(6) Uani 1 1 d . . . C32 C 0.38503(14) 0.5957(3) -0.03640(14) 0.0418(6) Uani 1 1 d . . . F32 F 0.39895(8) 0.54894(16) 0.02743(8) 0.0503(4) Uani 1 1 d . . . C33 C 0.44348(15) 0.6535(3) -0.04397(16) 0.0491(7) Uani 1 1 d . . . F33 F 0.50825(9) 0.66068(19) 0.00949(10) 0.0671(5) Uani 1 1 d . . . C34 C 0.43605(17) 0.7042(3) -0.10592(18) 0.0576(8) Uani 1 1 d . . . F34 F 0.49309(11) 0.7581(2) -0.11457(13) 0.0902(7) Uani 1 1 d . . . C35 C 0.37000(17) 0.6977(3) -0.15881(16) 0.0536(7) Uani 1 1 d . . . F35 F 0.36054(12) 0.7478(2) -0.22045(10) 0.0797(6) Uani 1 1 d . . . C36 C 0.31238(15) 0.6398(3) -0.14882(14) 0.0428(6) Uani 1 1 d . . . F36 F 0.24913(9) 0.63966(17) -0.20501(8) 0.0528(4) Uani 1 1 d . . . C41 C 0.24705(14) 0.5473(3) -0.00194(13) 0.0399(6) Uani 1 1 d . . . C42 C 0.27184(15) 0.6747(3) 0.03241(13) 0.0430(6) Uani 1 1 d . . . F42 F 0.30479(9) 0.77294(16) 0.00822(8) 0.0541(4) Uani 1 1 d . . . C43 C 0.26255(17) 0.7199(3) 0.08889(15) 0.0558(8) Uani 1 1 d . . . F43 F 0.28863(12) 0.8479(2) 0.11787(10) 0.0819(6) Uani 1 1 d . . . C44 C 0.22532(19) 0.6345(4) 0.11507(16) 0.0633(9) Uani 1 1 d . . . F44 F 0.21454(14) 0.6763(3) 0.16947(11) 0.0958(7) Uani 1 1 d . . . C45 C 0.19824(18) 0.5074(3) 0.08298(16) 0.0577(8) Uani 1 1 d . . . F45 F 0.15870(13) 0.4234(2) 0.10622(11) 0.0876(7) Uani 1 1 d . . . C46 C 0.20906(15) 0.4668(3) 0.02702(14) 0.0466(7) Uani 1 1 d . . . F46 F 0.17648(10) 0.34143(18) -0.00209(9) 0.0639(5) Uani 1 1 d . . . C51 C 0.11900(14) 0.7379(3) -0.09101(13) 0.0433(6) Uani 1 1 d . . . C52 C 0.07532(16) 0.6470(3) -0.07324(15) 0.0519(7) Uani 1 1 d . . . H52 H 0.0673 0.5522 -0.0898 0.062 Uiso 1 1 calc R . . C53 C 0.04341(18) 0.6950(4) -0.03125(16) 0.0642(9) Uani 1 1 d . . . H53 H 0.0136 0.6327 -0.0200 0.077 Uiso 1 1 calc R . . C54 C 0.0550(2) 0.8327(4) -0.00593(17) 0.0699(10) Uani 1 1 d . . . H54 H 0.0341 0.8640 0.0232 0.084 Uiso 1 1 calc R . . C55 C 0.0976(2) 0.9246(4) -0.02349(16) 0.0663(9) Uani 1 1 d . . . H55 H 0.1051 1.0194 -0.0070 0.080 Uiso 1 1 calc R . . C56 C 0.12939(17) 0.8767(3) -0.06576(14) 0.0514(7) Uani 1 1 d . . . H56 H 0.1585 0.9399 -0.0774 0.062 Uiso 1 1 calc R . . C61 C 0.4590(2) 0.3019(5) 0.3055(2) 0.0820(11) Uani 1 1 d . . . C62 C 0.4168(3) 0.3745(6) 0.2489(3) 0.0956(13) Uani 1 1 d . . . H62 H 0.4148 0.4751 0.2520 0.115 Uiso 1 1 calc R . . C63 C 0.3780(3) 0.3136(8) 0.1890(3) 0.1109(16) Uani 1 1 d . . . H63 H 0.3491 0.3695 0.1514 0.133 Uiso 1 1 calc R . . C64 C 0.3813(3) 0.1670(7) 0.1840(3) 0.1013(15) Uani 1 1 d . . . H64 H 0.3550 0.1223 0.1420 0.122 Uiso 1 1 calc R . . C65 C 0.4223(3) 0.0838(5) 0.2393(3) 0.0958(14) Uani 1 1 d . . . H65 H 0.4236 -0.0166 0.2350 0.115 Uiso 1 1 calc R . . C66 C 0.4616(2) 0.1493(5) 0.3012(3) 0.0945(13) Uani 1 1 d . . . H66 H 0.4894 0.0942 0.3396 0.113 Uiso 1 1 calc R . . C67 C 0.5068(3) 0.3715(7) 0.3709(3) 0.134(2) Uani 1 1 d . . . H67A H 0.5436 0.4271 0.3642 0.201 Uiso 1 1 calc R . . H67B H 0.5294 0.2980 0.4049 0.201 Uiso 1 1 calc R . . H67C H 0.4784 0.4345 0.3860 0.201 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N 0.0479(14) 0.0430(12) 0.0531(14) -0.0099(10) 0.0288(12) -0.0072(10) B 0.0327(16) 0.0414(16) 0.0393(15) 0.0011(12) 0.0143(13) -0.0015(12) C1 0.0434(16) 0.0425(15) 0.0548(17) -0.0047(12) 0.0235(14) -0.0024(12) C2 0.0371(15) 0.0375(14) 0.0494(15) -0.0012(11) 0.0191(12) -0.0033(11) O3 0.0371(10) 0.0366(9) 0.0454(10) -0.0023(7) 0.0165(8) 0.0012(7) C4 0.0388(15) 0.0379(14) 0.0434(14) 0.0002(11) 0.0160(12) -0.0002(11) C5 0.0407(16) 0.0464(15) 0.0436(15) -0.0038(12) 0.0191(13) 0.0034(12) C6 0.0433(17) 0.0626(18) 0.0465(16) -0.0046(13) 0.0161(14) -0.0019(14) C7 0.0408(17) 0.083(2) 0.0511(18) -0.0120(16) 0.0143(15) 0.0022(15) C8 0.060(2) 0.083(2) 0.0424(17) -0.0029(16) 0.0137(16) 0.0193(18) C9 0.066(2) 0.068(2) 0.0497(18) 0.0092(15) 0.0211(17) 0.0151(17) C10 0.0540(19) 0.0498(16) 0.0526(17) 0.0053(13) 0.0225(15) 0.0063(14) C11 0.066(2) 0.0526(17) 0.0597(19) -0.0069(14) 0.0373(17) -0.0096(15) C12 0.078(2) 0.074(2) 0.0566(19) -0.0045(16) 0.0392(18) -0.0148(18) C13 0.070(2) 0.087(2) 0.0541(19) 0.0022(17) 0.0270(18) 0.0023(19) C14 0.058(2) 0.082(2) 0.0533(18) -0.0140(16) 0.0271(16) -0.0098(17) C15 0.0436(17) 0.0608(18) 0.0549(17) -0.0118(14) 0.0253(14) -0.0105(14) C21 0.076(2) 0.0428(16) 0.075(2) -0.0077(15) 0.0414(19) 0.0020(15) C22 0.080(2) 0.0400(16) 0.090(2) -0.0014(16) 0.041(2) 0.0089(16) C23 0.061(2) 0.0396(16) 0.071(2) 0.0045(14) 0.0236(17) 0.0023(14) C24 0.0451(17) 0.0393(15) 0.0575(17) 0.0033(12) 0.0180(14) 0.0029(12) C31 0.0371(15) 0.0331(13) 0.0453(14) -0.0017(11) 0.0177(12) -0.0004(11) C32 0.0373(15) 0.0362(14) 0.0539(16) -0.0003(12) 0.0208(13) -0.0003(11) F32 0.0437(9) 0.0520(9) 0.0495(9) 0.0024(7) 0.0136(7) -0.0010(7) C33 0.0327(16) 0.0459(16) 0.0676(19) -0.0062(14) 0.0196(14) -0.0042(12) F33 0.0371(10) 0.0667(11) 0.0919(14) -0.0077(10) 0.0210(10) -0.0067(8) C34 0.0465(19) 0.0539(18) 0.087(2) 0.0038(16) 0.0423(18) -0.0061(14) F34 0.0661(13) 0.0965(15) 0.1321(19) 0.0118(13) 0.0652(13) -0.0165(11) C35 0.061(2) 0.0506(17) 0.0635(19) 0.0072(14) 0.0398(17) -0.0003(14) F35 0.0907(15) 0.0904(14) 0.0784(13) 0.0206(11) 0.0553(12) -0.0026(11) C36 0.0411(16) 0.0403(14) 0.0485(16) 0.0003(12) 0.0201(14) 0.0018(12) F36 0.0552(10) 0.0585(10) 0.0461(9) 0.0049(7) 0.0224(8) 0.0012(8) C41 0.0370(14) 0.0383(14) 0.0445(14) 0.0037(11) 0.0170(12) 0.0013(11) C42 0.0453(16) 0.0431(15) 0.0446(15) 0.0011(12) 0.0226(13) 0.0004(12) F42 0.0642(11) 0.0408(8) 0.0662(10) -0.0066(7) 0.0360(9) -0.0080(7) C43 0.0582(19) 0.0570(18) 0.0527(17) -0.0133(14) 0.0232(15) -0.0016(15) F43 0.1007(16) 0.0731(13) 0.0860(14) -0.0401(11) 0.0527(13) -0.0212(11) C44 0.074(2) 0.078(2) 0.0502(17) -0.0064(16) 0.0374(17) 0.0001(18) F44 0.1197(19) 0.1214(18) 0.0740(13) -0.0286(12) 0.0677(14) -0.0170(15) C45 0.066(2) 0.0618(19) 0.0589(18) 0.0079(15) 0.0389(17) -0.0036(16) F45 0.1115(17) 0.0914(15) 0.0953(15) 0.0059(12) 0.0784(14) -0.0146(12) C46 0.0484(17) 0.0445(15) 0.0501(16) 0.0001(12) 0.0237(14) -0.0025(13) F46 0.0756(13) 0.0538(10) 0.0787(12) -0.0093(9) 0.0485(10) -0.0205(9) C51 0.0371(15) 0.0481(15) 0.0406(14) -0.0014(12) 0.0119(12) 0.0067(12) C52 0.0485(18) 0.0567(18) 0.0535(17) 0.0010(14) 0.0240(14) 0.0051(14) C53 0.056(2) 0.083(2) 0.0617(19) 0.0096(17) 0.0321(17) 0.0118(17) C54 0.073(2) 0.086(3) 0.0577(19) 0.0016(18) 0.0339(18) 0.029(2) C55 0.076(2) 0.063(2) 0.0582(19) -0.0049(16) 0.0260(18) 0.0198(18) C56 0.0566(19) 0.0489(16) 0.0469(16) -0.0015(13) 0.0193(14) 0.0101(14) C61 0.074(3) 0.098(3) 0.080(3) -0.013(2) 0.038(2) -0.013(2) C62 0.085(3) 0.105(3) 0.101(3) 0.028(3) 0.042(3) 0.019(3) C63 0.081(3) 0.161(6) 0.091(4) 0.000(3) 0.036(3) 0.001(3) C64 0.101(4) 0.122(4) 0.106(4) -0.016(3) 0.067(3) -0.015(3) C65 0.101(4) 0.087(3) 0.128(4) -0.015(3) 0.076(3) -0.011(3) C66 0.082(3) 0.103(3) 0.110(4) 0.010(3) 0.051(3) 0.001(3) C67 0.145(5) 0.149(5) 0.107(4) 0.003(4) 0.050(4) -0.024(4) _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 N C11 1.282(4) . ? N C15 1.480(4) . ? N C1 1.495(4) . ? B O3 1.482(3) . ? B C2 1.660(4) . ? B C41 1.680(4) . ? B C31 1.685(4) . ? C1 C21 1.539(4) . ? C1 C2 1.541(4) . ? C1 H1 0.9900 . ? C2 C24 1.544(4) . ? C2 H2 0.9900 . ? O3 C4 1.422(3) . ? C4 C5 1.516(4) . ? C4 C51 1.525(4) . ? C4 H4 0.9900 . ? C5 C10 1.387(4) . ? C5 C6 1.390(4) . ? C6 C7 1.382(4) . ? C6 H6 0.9400 . ? C7 C8 1.386(5) . ? C7 H7 0.9400 . ? C8 C9 1.368(5) . ? C8 H8 0.9400 . ? C9 C10 1.387(4) . ? C9 H9 0.9400 . ? C10 H10 0.9400 . ? C11 C12 1.479(4) . ? C11 H11 0.9400 . ? C12 C13 1.508(5) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C13 C14 1.501(5) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C14 C15 1.510(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C21 C22 1.514(5) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C22 C23 1.512(5) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C23 C24 1.525(4) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C31 C36 1.384(4) . ? C31 C32 1.390(4) . ? C32 F32 1.359(3) . ? C32 C33 1.376(4) . ? C33 F33 1.350(3) . ? C33 C34 1.366(4) . ? C34 F34 1.347(3) . ? C34 C35 1.361(4) . ? C35 F35 1.347(3) . ? C35 C36 1.387(4) . ? C36 F36 1.358(3) . ? C41 C42 1.379(4) . ? C41 C46 1.396(4) . ? C42 F42 1.358(3) . ? C42 C43 1.374(4) . ? C43 F43 1.348(3) . ? C43 C44 1.371(5) . ? C44 F44 1.338(3) . ? C44 C45 1.366(5) . ? C45 F45 1.358(3) . ? C45 C46 1.367(4) . ? C46 F46 1.361(3) . ? C51 C56 1.383(4) . ? C51 C52 1.391(4) . ? C52 C53 1.389(4) . ? C52 H52 0.9400 . ? C53 C54 1.374(5) . ? C53 H53 0.9400 . ? C54 C55 1.376(5) . ? C54 H54 0.9400 . ? C55 C56 1.392(4) . ? C55 H55 0.9400 . ? C56 H56 0.9400 . ? C61 C62 1.350(6) . ? C61 C66 1.425(6) . ? C61 C67 1.492(6) . ? C62 C63 1.333(7) . ? C62 H62 0.9400 . ? C63 C64 1.371(7) . ? C63 H63 0.9400 . ? C64 C65 1.378(7) . ? C64 H64 0.9400 . ? C65 C66 1.385(6) . ? C65 H65 0.9400 . ? C66 H66 0.9400 . ? C67 H67A 0.9700 . ? C67 H67B 0.9700 . ? C67 H67C 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 N C15 122.2(3) . . ? C11 N C1 120.0(3) . . ? C15 N C1 117.7(2) . . ? O3 B C2 108.5(2) . . ? O3 B C41 106.2(2) . . ? C2 B C41 111.1(2) . . ? O3 B C31 112.7(2) . . ? C2 B C31 107.4(2) . . ? C41 B C31 111.0(2) . . ? N C1 C21 107.1(2) . . ? N C1 C2 114.5(2) . . ? C21 C1 C2 113.5(2) . . ? N C1 H1 107.1 . . ? C21 C1 H1 107.1 . . ? C2 C1 H1 107.1 . . ? C1 C2 C24 104.6(2) . . ? C1 C2 B 118.2(2) . . ? C24 C2 B 112.5(2) . . ? C1 C2 H2 107.0 . . ? C24 C2 H2 107.0 . . ? B C2 H2 107.0 . . ? C4 O3 B 121.38(19) . . ? O3 C4 C5 108.3(2) . . ? O3 C4 C51 113.5(2) . . ? C5 C4 C51 109.3(2) . . ? O3 C4 H4 108.5 . . ? C5 C4 H4 108.5 . . ? C51 C4 H4 108.5 . . ? C10 C5 C6 117.7(3) . . ? C10 C5 C4 121.3(2) . . ? C6 C5 C4 121.0(2) . . ? C7 C6 C5 121.2(3) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C6 C7 C8 120.1(3) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C9 C8 C7 119.3(3) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C8 C9 C10 120.6(3) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C9 C10 C5 121.0(3) . . ? C9 C10 H10 119.5 . . ? C5 C10 H10 119.5 . . ? N C11 C12 124.9(3) . . ? N C11 H11 117.6 . . ? C12 C11 H11 117.6 . . ? C11 C12 C13 113.3(3) . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12B 108.9 . . ? C13 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C14 C13 C12 110.2(3) . . ? C14 C13 H13A 109.6 . . ? C12 C13 H13A 109.6 . . ? C14 C13 H13B 109.6 . . ? C12 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? C13 C14 C15 111.3(3) . . ? C13 C14 H14A 109.4 . . ? C15 C14 H14A 109.4 . . ? C13 C14 H14B 109.4 . . ? C15 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? N C15 C14 112.4(2) . . ? N C15 H15A 109.1 . . ? C14 C15 H15A 109.1 . . ? N C15 H15B 109.1 . . ? C14 C15 H15B 109.1 . . ? H15A C15 H15B 107.9 . . ? C22 C21 C1 111.6(3) . . ? C22 C21 H21A 109.3 . . ? C1 C21 H21A 109.3 . . ? C22 C21 H21B 109.3 . . ? C1 C21 H21B 109.3 . . ? H21A C21 H21B 108.0 . . ? C23 C22 C21 111.0(3) . . ? C23 C22 H22A 109.4 . . ? C21 C22 H22A 109.4 . . ? C23 C22 H22B 109.4 . . ? C21 C22 H22B 109.4 . . ? H22A C22 H22B 108.0 . . ? C22 C23 C24 110.4(3) . . ? C22 C23 H23A 109.6 . . ? C24 C23 H23A 109.6 . . ? C22 C23 H23B 109.6 . . ? C24 C23 H23B 109.6 . . ? H23A C23 H23B 108.1 . . ? C23 C24 C2 114.5(2) . . ? C23 C24 H24A 108.6 . . ? C2 C24 H24A 108.6 . . ? C23 C24 H24B 108.6 . . ? C2 C24 H24B 108.6 . . ? H24A C24 H24B 107.6 . . ? C36 C31 C32 112.1(2) . . ? C36 C31 B 124.9(2) . . ? C32 C31 B 122.8(2) . . ? F32 C32 C33 114.6(2) . . ? F32 C32 C31 120.5(2) . . ? C33 C32 C31 124.9(3) . . ? F33 C33 C34 119.7(3) . . ? F33 C33 C32 120.4(3) . . ? C34 C33 C32 119.9(3) . . ? F34 C34 C35 120.7(3) . . ? F34 C34 C33 120.6(3) . . ? C35 C34 C33 118.6(3) . . ? F35 C35 C34 120.2(3) . . ? F35 C35 C36 120.1(3) . . ? C34 C35 C36 119.6(3) . . ? F36 C36 C31 120.6(2) . . ? F36 C36 C35 114.4(2) . . ? C31 C36 C35 124.9(3) . . ? C42 C41 C46 111.6(2) . . ? C42 C41 B 125.6(2) . . ? C46 C41 B 121.9(2) . . ? F42 C42 C43 113.9(2) . . ? F42 C42 C41 120.0(2) . . ? C43 C42 C41 125.9(3) . . ? F43 C43 C44 120.0(3) . . ? F43 C43 C42 120.6(3) . . ? C44 C43 C42 119.4(3) . . ? F44 C44 C45 121.2(3) . . ? F44 C44 C43 120.8(3) . . ? C45 C44 C43 117.9(3) . . ? F45 C45 C44 119.2(3) . . ? F45 C45 C46 120.2(3) . . ? C44 C45 C46 120.6(3) . . ? F46 C46 C45 114.8(2) . . ? F46 C46 C41 120.5(2) . . ? C45 C46 C41 124.7(3) . . ? C56 C51 C52 118.0(3) . . ? C56 C51 C4 119.9(3) . . ? C52 C51 C4 122.0(2) . . ? C53 C52 C51 120.6(3) . . ? C53 C52 H52 119.7 . . ? C51 C52 H52 119.7 . . ? C54 C53 C52 120.6(3) . . ? C54 C53 H53 119.7 . . ? C52 C53 H53 119.7 . . ? C53 C54 C55 119.6(3) . . ? C53 C54 H54 120.2 . . ? C55 C54 H54 120.2 . . ? C54 C55 C56 119.8(3) . . ? C54 C55 H55 120.1 . . ? C56 C55 H55 120.1 . . ? C51 C56 C55 121.3(3) . . ? C51 C56 H56 119.3 . . ? C55 C56 H56 119.3 . . ? C62 C61 C66 117.8(4) . . ? C62 C61 C67 124.3(5) . . ? C66 C61 C67 117.8(5) . . ? C63 C62 C61 124.6(5) . . ? C63 C62 H62 117.7 . . ? C61 C62 H62 117.7 . . ? C62 C63 C64 118.0(6) . . ? C62 C63 H63 121.0 . . ? C64 C63 H63 121.0 . . ? C63 C64 C65 121.5(5) . . ? C63 C64 H64 119.3 . . ? C65 C64 H64 119.3 . . ? C64 C65 C66 119.5(5) . . ? C64 C65 H65 120.3 . . ? C66 C65 H65 120.3 . . ? C65 C66 C61 118.6(5) . . ? C65 C66 H66 120.7 . . ? C61 C66 H66 120.7 . . ? C61 C67 H67A 109.5 . . ? C61 C67 H67B 109.5 . . ? H67A C67 H67B 109.5 . . ? C61 C67 H67C 109.5 . . ? H67A C67 H67C 109.5 . . ? H67B C67 H67C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N C1 C21 -99.0(3) . . . . ? C15 N C1 C21 77.4(3) . . . . ? C11 N C1 C2 134.3(3) . . . . ? C15 N C1 C2 -49.3(3) . . . . ? N C1 C2 C24 179.5(2) . . . . ? C21 C1 C2 C24 56.2(3) . . . . ? N C1 C2 B -54.5(3) . . . . ? C21 C1 C2 B -177.8(2) . . . . ? O3 B C2 C1 76.3(3) . . . . ? C41 B C2 C1 -167.3(2) . . . . ? C31 B C2 C1 -45.8(3) . . . . ? O3 B C2 C24 -161.6(2) . . . . ? C41 B C2 C24 -45.3(3) . . . . ? C31 B C2 C24 76.3(3) . . . . ? C2 B O3 C4 -177.9(2) . . . . ? C41 B O3 C4 62.6(3) . . . . ? C31 B O3 C4 -59.0(3) . . . . ? B O3 C4 C5 153.7(2) . . . . ? B O3 C4 C51 -84.7(3) . . . . ? O3 C4 C5 C10 -127.5(3) . . . . ? C51 C4 C5 C10 108.3(3) . . . . ? O3 C4 C5 C6 52.5(3) . . . . ? C51 C4 C5 C6 -71.6(3) . . . . ? C10 C5 C6 C7 -0.2(4) . . . . ? C4 C5 C6 C7 179.8(3) . . . . ? C5 C6 C7 C8 -0.1(5) . . . . ? C6 C7 C8 C9 0.1(5) . . . . ? C7 C8 C9 C10 0.1(5) . . . . ? C8 C9 C10 C5 -0.4(5) . . . . ? C6 C5 C10 C9 0.4(4) . . . . ? C4 C5 C10 C9 -179.5(3) . . . . ? C15 N C11 C12 2.5(4) . . . . ? C1 N C11 C12 178.8(3) . . . . ? N C11 C12 C13 9.8(5) . . . . ? C11 C12 C13 C14 -39.7(4) . . . . ? C12 C13 C14 C15 58.6(4) . . . . ? C11 N C15 C14 16.1(4) . . . . ? C1 N C15 C14 -160.2(2) . . . . ? C13 C14 C15 N -46.6(4) . . . . ? N C1 C21 C22 175.5(2) . . . . ? C2 C1 C21 C22 -57.2(4) . . . . ? C1 C21 C22 C23 53.6(4) . . . . ? C21 C22 C23 C24 -53.8(4) . . . . ? C22 C23 C24 C2 58.9(4) . . . . ? C1 C2 C24 C23 -57.8(3) . . . . ? B C2 C24 C23 172.7(2) . . . . ? O3 B C31 C36 -23.5(3) . . . . ? C2 B C31 C36 96.0(3) . . . . ? C41 B C31 C36 -142.4(2) . . . . ? O3 B C31 C32 161.7(2) . . . . ? C2 B C31 C32 -78.8(3) . . . . ? C41 B C31 C32 42.8(3) . . . . ? C36 C31 C32 F32 179.3(2) . . . . ? B C31 C32 F32 -5.3(4) . . . . ? C36 C31 C32 C33 0.3(4) . . . . ? B C31 C32 C33 175.7(2) . . . . ? F32 C32 C33 F33 0.0(4) . . . . ? C31 C32 C33 F33 179.0(2) . . . . ? F32 C32 C33 C34 -180.0(2) . . . . ? C31 C32 C33 C34 -0.9(4) . . . . ? F33 C33 C34 F34 1.6(4) . . . . ? C32 C33 C34 F34 -178.4(3) . . . . ? F33 C33 C34 C35 -179.1(3) . . . . ? C32 C33 C34 C35 0.9(4) . . . . ? F34 C34 C35 F35 -1.3(5) . . . . ? C33 C34 C35 F35 179.4(3) . . . . ? F34 C34 C35 C36 179.0(3) . . . . ? C33 C34 C35 C36 -0.3(4) . . . . ? C32 C31 C36 F36 -179.6(2) . . . . ? B C31 C36 F36 5.0(4) . . . . ? C32 C31 C36 C35 0.4(4) . . . . ? B C31 C36 C35 -175.0(3) . . . . ? F35 C35 C36 F36 -0.1(4) . . . . ? C34 C35 C36 F36 179.6(3) . . . . ? F35 C35 C36 C31 179.9(3) . . . . ? C34 C35 C36 C31 -0.4(4) . . . . ? O3 B C41 C42 -93.9(3) . . . . ? C2 B C41 C42 148.3(3) . . . . ? C31 B C41 C42 28.9(3) . . . . ? O3 B C41 C46 74.5(3) . . . . ? C2 B C41 C46 -43.3(3) . . . . ? C31 B C41 C46 -162.7(2) . . . . ? C46 C41 C42 F42 -174.4(2) . . . . ? B C41 C42 F42 -5.0(4) . . . . ? C46 C41 C42 C43 1.0(4) . . . . ? B C41 C42 C43 170.4(3) . . . . ? F42 C42 C43 F43 -3.6(4) . . . . ? C41 C42 C43 F43 -179.3(3) . . . . ? F42 C42 C43 C44 175.3(3) . . . . ? C41 C42 C43 C44 -0.4(5) . . . . ? F43 C43 C44 F44 -0.2(5) . . . . ? C42 C43 C44 F44 -179.1(3) . . . . ? F43 C43 C44 C45 178.3(3) . . . . ? C42 C43 C44 C45 -0.6(5) . . . . ? F44 C44 C45 F45 1.1(5) . . . . ? C43 C44 C45 F45 -177.4(3) . . . . ? F44 C44 C45 C46 179.3(3) . . . . ? C43 C44 C45 C46 0.8(5) . . . . ? F45 C45 C46 F46 1.2(4) . . . . ? C44 C45 C46 F46 -177.0(3) . . . . ? F45 C45 C46 C41 178.1(3) . . . . ? C44 C45 C46 C41 -0.1(5) . . . . ? C42 C41 C46 F46 176.0(2) . . . . ? B C41 C46 F46 6.1(4) . . . . ? C42 C41 C46 C45 -0.8(4) . . . . ? B C41 C46 C45 -170.7(3) . . . . ? O3 C4 C51 C56 144.5(2) . . . . ? C5 C4 C51 C56 -94.5(3) . . . . ? O3 C4 C51 C52 -37.7(3) . . . . ? C5 C4 C51 C52 83.3(3) . . . . ? C56 C51 C52 C53 -0.1(4) . . . . ? C4 C51 C52 C53 -178.0(3) . . . . ? C51 C52 C53 C54 -0.7(5) . . . . ? C52 C53 C54 C55 1.3(5) . . . . ? C53 C54 C55 C56 -1.1(5) . . . . ? C52 C51 C56 C55 0.4(4) . . . . ? C4 C51 C56 C55 178.3(3) . . . . ? C54 C55 C56 C51 0.2(5) . . . . ? C66 C61 C62 C63 -0.7(7) . . . . ? C67 C61 C62 C63 175.0(5) . . . . ? C61 C62 C63 C64 -0.6(8) . . . . ? C62 C63 C64 C65 1.3(7) . . . . ? C63 C64 C65 C66 -0.6(7) . . . . ? C64 C65 C66 C61 -0.7(6) . . . . ? C62 C61 C66 C65 1.4(6) . . . . ? C67 C61 C66 C65 -174.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 67.04 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.341 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.049