# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_pt395m _database_code_depnum_ccdc_archive 'CCDC 901484' #TrackingRef '- Cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H40 B2 F2 N2' _chemical_formula_weight 572.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 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 18.770(2) _cell_length_b 9.8560(13) _cell_length_c 16.662(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.167(8) _cell_angle_gamma 90.00 _cell_volume 3082.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7805 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 29.72 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9930 _exptl_absorpt_correction_T_max 0.9945 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker kappa apex ccd' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 49266 _diffrn_reflns_av_R_equivalents 0.1077 _diffrn_reflns_av_sigmaI/netI 0.0906 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 28.00 _reflns_number_total 7401 _reflns_number_gt 4649 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Kappa Apex ccd' _computing_cell_refinement 'bruker saint' _computing_data_reduction 'bruker saint' _computing_structure_solution SHELXS-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ORTEP-III _computing_publication_material WinGXv1.80.05 _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^)+(0.0858P)^2^+26.2089P] 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 7401 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1890 _refine_ls_R_factor_gt 0.1390 _refine_ls_wR_factor_ref 0.3567 _refine_ls_wR_factor_gt 0.3285 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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 F1 F 1.2189(2) 0.1918(4) 0.3383(2) 0.0398(9) Uani 1 1 d . . . F2 F 1.1980(2) -0.0319(4) 0.3607(2) 0.0392(9) Uani 1 1 d . . . N1 N 1.1318(3) 0.0806(5) 0.2549(3) 0.0234(10) Uani 1 1 d . . . N2 N 1.1072(3) 0.1300(5) 0.3980(3) 0.0253(10) Uani 1 1 d . . . B1 B 1.1672(4) 0.0915(7) 0.3390(4) 0.0270(14) Uani 1 1 d . . . B2 B 0.7026(4) 0.0904(7) 0.2448(4) 0.0253(13) Uani 1 1 d . . . C1 C 1.0104(3) 0.0974(5) 0.3048(3) 0.0221(11) Uani 1 1 d . . . C2 C 1.0586(3) 0.0747(5) 0.2421(3) 0.0226(11) Uani 1 1 d . . . C3 C 1.0465(3) 0.0541(6) 0.1580(3) 0.0259(12) Uani 1 1 d . . . C4 C 1.1138(3) 0.0487(6) 0.1232(3) 0.0284(13) Uani 1 1 d . . . H4 H 1.1231 0.0361 0.0689 0.034 Uiso 1 1 calc R . . C5 C 1.1652(3) 0.0653(6) 0.1835(3) 0.0266(12) Uani 1 1 d . . . C6 C 1.0342(3) 0.1269(5) 0.3819(3) 0.0219(11) Uani 1 1 d . . . C7 C 0.9968(3) 0.1578(6) 0.4553(3) 0.0236(12) Uani 1 1 d . . . C8 C 1.0489(3) 0.1756(6) 0.5129(3) 0.0269(12) Uani 1 1 d . . . H8 H 1.0410 0.1955 0.5667 0.032 Uiso 1 1 calc R . . C9 C 1.1161(3) 0.1588(6) 0.4768(3) 0.0256(12) Uani 1 1 d . . . C10 C 0.9782(3) 0.0411(7) 0.1136(3) 0.0301(13) Uani 1 1 d . . . H10A H 0.9392 0.0480 0.1506 0.045 Uiso 1 1 calc R . . H10B H 0.9765 -0.0453 0.0871 0.045 Uiso 1 1 calc R . . H10C H 0.9746 0.1123 0.0745 0.045 Uiso 1 1 calc R . . C11 C 1.2444(3) 0.0692(7) 0.1760(4) 0.0316(13) Uani 1 1 d . . . H11A H 1.2653 0.0822 0.2281 0.047 Uiso 1 1 calc R . . H11B H 1.2578 0.1427 0.1414 0.047 Uiso 1 1 calc R . . H11C H 1.2609 -0.0149 0.1537 0.047 Uiso 1 1 calc R . . C12 C 0.9189(3) 0.1696(6) 0.4701(3) 0.0279(13) Uani 1 1 d . . . H12A H 0.8934 0.1531 0.4210 0.042 Uiso 1 1 calc R . . H12B H 0.9082 0.2592 0.4892 0.042 Uiso 1 1 calc R . . H12C H 0.9048 0.1041 0.5096 0.042 Uiso 1 1 calc R . . C13 C 1.1881(4) 0.1656(7) 0.5150(4) 0.0341(14) Uani 1 1 d . . . H13A H 1.2240 0.1498 0.4752 0.051 Uiso 1 1 calc R . . H13B H 1.1916 0.0977 0.5562 0.051 Uiso 1 1 calc R . . H13C H 1.1949 0.2538 0.5384 0.051 Uiso 1 1 calc R . . C14 C 0.9334(3) 0.0929(6) 0.2892(3) 0.0227(11) Uani 1 1 d . . . C15 C 0.8962(3) -0.0295(6) 0.2789(3) 0.0241(12) Uani 1 1 d . . . H15 H 0.9207 -0.1113 0.2829 0.029 Uiso 1 1 calc R . . C16 C 0.8247(3) -0.0305(6) 0.2631(3) 0.0230(11) Uani 1 1 d . . . H16 H 0.8017 -0.1130 0.2551 0.028 Uiso 1 1 calc R . . C17 C 0.7852(3) 0.0901(6) 0.2586(3) 0.0223(11) Uani 1 1 d . . . C18 C 0.8227(3) 0.2115(6) 0.2676(3) 0.0257(12) Uani 1 1 d . . . H18 H 0.7980 0.2930 0.2648 0.031 Uiso 1 1 calc R . . C19 C 0.8945(3) 0.2143(6) 0.2803(3) 0.0262(12) Uani 1 1 d . . . H19 H 0.9181 0.2972 0.2831 0.031 Uiso 1 1 calc R . . C20 C 0.6584(3) 0.2115(6) 0.2824(3) 0.0241(12) Uani 1 1 d . . . C21 C 0.6213(3) 0.3049(6) 0.2339(3) 0.0248(12) Uani 1 1 d . . . C22 C 0.5841(3) 0.4111(6) 0.2682(4) 0.0277(12) Uani 1 1 d . . . H22 H 0.5616 0.4736 0.2348 0.033 Uiso 1 1 calc R . . C23 C 0.5792(3) 0.4280(6) 0.3519(4) 0.0285(13) Uani 1 1 d . . . C24 C 0.6163(3) 0.3363(6) 0.3992(3) 0.0268(12) Uani 1 1 d . . . H24 H 0.6141 0.3452 0.4547 0.032 Uiso 1 1 calc R . . C25 C 0.6566(3) 0.2313(6) 0.3670(3) 0.0258(12) Uani 1 1 d . . . C26 C 0.6247(3) 0.2969(7) 0.1434(3) 0.0299(13) Uani 1 1 d . . . H26A H 0.6527 0.2198 0.1280 0.045 Uiso 1 1 calc R . . H26B H 0.6461 0.3781 0.1228 0.045 Uiso 1 1 calc R . . H26C H 0.5774 0.2878 0.1221 0.045 Uiso 1 1 calc R . . C27 C 0.5367(4) 0.5414(7) 0.3873(4) 0.0352(14) Uani 1 1 d . . . H27A H 0.5153 0.5936 0.3449 0.053 Uiso 1 1 calc R . . H27B H 0.5674 0.5987 0.4186 0.053 Uiso 1 1 calc R . . H27C H 0.5001 0.5048 0.4210 0.053 Uiso 1 1 calc R . . C28 C 0.6968(4) 0.1406(7) 0.4240(4) 0.0349(14) Uani 1 1 d . . . H28A H 0.7217 0.0723 0.3941 0.052 Uiso 1 1 calc R . . H28B H 0.6640 0.0980 0.4601 0.052 Uiso 1 1 calc R . . H28C H 0.7304 0.1937 0.4541 0.052 Uiso 1 1 calc R . . C29 C 0.6672(3) -0.0253(6) 0.1935(3) 0.0247(12) Uani 1 1 d . . . C30 C 0.6875(3) -0.0476(6) 0.1132(3) 0.0273(13) Uani 1 1 d . . . C31 C 0.6525(3) -0.1453(6) 0.0676(3) 0.0275(13) Uani 1 1 d . . . H31 H 0.6641 -0.1549 0.0136 0.033 Uiso 1 1 calc R . . C32 C 0.6009(3) -0.2284(6) 0.1002(4) 0.0277(12) Uani 1 1 d . . . C33 C 0.5832(3) -0.2112(6) 0.1801(3) 0.0279(13) Uani 1 1 d . . . H33 H 0.5497 -0.2686 0.2031 0.034 Uiso 1 1 calc R . . C34 C 0.6142(3) -0.1107(6) 0.2270(3) 0.0256(12) Uani 1 1 d . . . C36 C 0.7471(3) 0.0317(7) 0.0740(4) 0.0330(14) Uani 1 1 d . . . H36A H 0.7654 0.0975 0.1112 0.050 Uiso 1 1 calc R . . H36B H 0.7291 0.0773 0.0272 0.050 Uiso 1 1 calc R . . H36C H 0.7845 -0.0293 0.0587 0.050 Uiso 1 1 calc R . . C37 C 0.5628(4) -0.3346(7) 0.0497(4) 0.0392(16) Uani 1 1 d . . . H37A H 0.5817 -0.3338 -0.0038 0.059 Uiso 1 1 calc R . . H37B H 0.5128 -0.3146 0.0479 0.059 Uiso 1 1 calc R . . H37C H 0.5699 -0.4227 0.0730 0.059 Uiso 1 1 calc R . . C38 C 0.5918(4) -0.0992(7) 0.3138(3) 0.0340(14) Uani 1 1 d . . . H38A H 0.6176 -0.0266 0.3390 0.051 Uiso 1 1 calc R . . H38B H 0.6019 -0.1828 0.3410 0.051 Uiso 1 1 calc R . . H38C H 0.5416 -0.0808 0.3163 0.051 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 F1 0.041(2) 0.040(2) 0.038(2) 0.0011(17) -0.0021(17) -0.0092(18) F2 0.051(2) 0.035(2) 0.0319(19) 0.0013(16) -0.0039(17) 0.0111(18) N1 0.034(3) 0.017(2) 0.020(2) 0.0032(18) 0.0042(19) 0.0024(19) N2 0.035(3) 0.018(2) 0.023(2) 0.0007(19) 0.0008(19) 0.000(2) B1 0.029(3) 0.030(4) 0.023(3) 0.007(3) 0.001(2) 0.003(3) B2 0.032(3) 0.025(3) 0.019(3) 0.006(2) 0.004(2) 0.000(3) C1 0.035(3) 0.015(3) 0.016(2) 0.003(2) -0.001(2) 0.001(2) C2 0.032(3) 0.015(3) 0.021(3) 0.003(2) 0.001(2) 0.003(2) C3 0.037(3) 0.016(3) 0.025(3) 0.000(2) 0.003(2) 0.003(2) C4 0.039(3) 0.025(3) 0.021(3) 0.001(2) 0.002(2) 0.002(2) C5 0.035(3) 0.023(3) 0.022(3) 0.002(2) 0.005(2) 0.004(2) C6 0.035(3) 0.017(3) 0.014(2) -0.002(2) -0.001(2) 0.001(2) C7 0.032(3) 0.019(3) 0.019(3) 0.000(2) 0.003(2) -0.001(2) C8 0.036(3) 0.024(3) 0.021(3) -0.002(2) 0.001(2) -0.004(2) C9 0.035(3) 0.019(3) 0.022(3) -0.001(2) -0.004(2) -0.005(2) C10 0.037(3) 0.031(3) 0.022(3) 0.000(2) 0.001(2) 0.000(3) C11 0.031(3) 0.037(4) 0.027(3) 0.003(3) 0.002(2) 0.003(3) C12 0.034(3) 0.025(3) 0.024(3) -0.001(2) 0.002(2) -0.001(2) C13 0.041(4) 0.033(4) 0.028(3) 0.000(3) -0.007(3) -0.003(3) C14 0.035(3) 0.020(3) 0.013(2) 0.003(2) 0.000(2) 0.002(2) C15 0.035(3) 0.019(3) 0.019(2) 0.001(2) 0.003(2) 0.003(2) C16 0.036(3) 0.017(3) 0.016(2) -0.003(2) 0.002(2) -0.001(2) C17 0.032(3) 0.021(3) 0.014(2) 0.000(2) 0.001(2) 0.001(2) C18 0.034(3) 0.022(3) 0.021(3) 0.002(2) 0.000(2) 0.001(2) C19 0.033(3) 0.021(3) 0.025(3) 0.001(2) 0.003(2) 0.000(2) C20 0.026(3) 0.026(3) 0.020(3) -0.001(2) 0.001(2) -0.004(2) C21 0.024(3) 0.028(3) 0.022(3) 0.002(2) -0.001(2) -0.002(2) C22 0.034(3) 0.022(3) 0.028(3) 0.004(2) -0.002(2) 0.000(2) C23 0.028(3) 0.025(3) 0.033(3) -0.005(2) 0.003(2) -0.005(2) C24 0.028(3) 0.031(3) 0.021(3) -0.004(2) 0.002(2) -0.003(2) C25 0.029(3) 0.028(3) 0.020(3) -0.001(2) 0.000(2) -0.005(2) C26 0.039(3) 0.032(3) 0.019(3) 0.004(2) 0.000(2) 0.003(3) C27 0.037(4) 0.035(4) 0.034(3) -0.008(3) 0.001(3) -0.001(3) C28 0.046(4) 0.037(4) 0.022(3) -0.002(3) -0.002(3) 0.002(3) C29 0.027(3) 0.026(3) 0.021(3) 0.003(2) -0.001(2) 0.003(2) C30 0.030(3) 0.030(3) 0.022(3) -0.002(2) 0.004(2) 0.005(2) C31 0.032(3) 0.032(3) 0.019(3) -0.001(2) 0.000(2) 0.008(2) C32 0.029(3) 0.025(3) 0.029(3) 0.004(2) -0.003(2) 0.008(2) C33 0.037(3) 0.020(3) 0.027(3) 0.003(2) 0.002(2) 0.001(2) C34 0.029(3) 0.023(3) 0.025(3) 0.000(2) -0.001(2) 0.001(2) C36 0.033(3) 0.044(4) 0.022(3) 0.003(3) 0.004(2) -0.002(3) C37 0.055(4) 0.031(4) 0.032(3) -0.006(3) -0.001(3) -0.001(3) C38 0.039(4) 0.041(4) 0.022(3) 0.003(3) 0.002(2) -0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 B1 1.385(8) . ? F2 B1 1.394(8) . ? N1 C5 1.355(7) . ? N1 C2 1.390(8) . ? N1 B1 1.553(8) . ? N2 C9 1.353(7) . ? N2 C6 1.396(8) . ? N2 B1 1.544(8) . ? B2 C17 1.568(9) . ? B2 C29 1.571(9) . ? B2 C20 1.584(9) . ? C1 C6 1.390(7) . ? C1 C2 1.402(7) . ? C1 C14 1.468(8) . ? C2 C3 1.435(8) . ? C3 C4 1.391(8) . ? C3 C10 1.484(9) . ? C4 C5 1.400(9) . ? C5 C11 1.492(8) . ? C6 C7 1.444(7) . ? C7 C8 1.380(8) . ? C7 C12 1.489(8) . ? C8 C9 1.408(8) . ? C9 C13 1.493(9) . ? C14 C15 1.404(8) . ? C14 C19 1.409(8) . ? C15 C16 1.368(8) . ? C16 C17 1.402(8) . ? C17 C18 1.395(8) . ? C18 C19 1.364(8) . ? C20 C21 1.407(8) . ? C20 C25 1.423(7) . ? C21 C22 1.383(8) . ? C21 C26 1.510(8) . ? C22 C23 1.408(8) . ? C23 C24 1.385(9) . ? C23 C27 1.496(8) . ? C24 C25 1.390(8) . ? C25 C28 1.506(9) . ? C29 C30 1.410(7) . ? C29 C34 1.419(8) . ? C30 C31 1.391(9) . ? C30 C36 1.515(8) . ? C31 C32 1.381(8) . ? C32 C33 1.384(8) . ? C32 C37 1.520(9) . ? C33 C34 1.388(8) . ? C34 C38 1.511(8) . ? 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 C5 N1 C2 108.7(5) . . ? C5 N1 B1 127.0(5) . . ? C2 N1 B1 124.2(4) . . ? C9 N2 C6 108.0(5) . . ? C9 N2 B1 125.6(5) . . ? C6 N2 B1 126.1(5) . . ? F1 B1 F2 109.6(5) . . ? F1 B1 N2 110.0(5) . . ? F2 B1 N2 110.6(5) . . ? F1 B1 N1 109.9(5) . . ? F2 B1 N1 110.5(5) . . ? N2 B1 N1 106.3(5) . . ? C17 B2 C29 119.7(5) . . ? C17 B2 C20 117.5(5) . . ? C29 B2 C20 122.7(5) . . ? C6 C1 C2 120.9(5) . . ? C6 C1 C14 119.0(5) . . ? C2 C1 C14 120.1(5) . . ? N1 C2 C1 121.3(5) . . ? N1 C2 C3 108.0(5) . . ? C1 C2 C3 130.5(5) . . ? C4 C3 C2 105.7(5) . . ? C4 C3 C10 125.0(5) . . ? C2 C3 C10 129.3(5) . . ? C3 C4 C5 108.7(5) . . ? N1 C5 C4 108.9(5) . . ? N1 C5 C11 122.3(5) . . ? C4 C5 C11 128.8(5) . . ? C1 C6 N2 119.7(5) . . ? C1 C6 C7 132.1(5) . . ? N2 C6 C7 108.2(5) . . ? C8 C7 C6 105.7(5) . . ? C8 C7 C12 124.7(5) . . ? C6 C7 C12 129.6(5) . . ? C7 C8 C9 108.7(5) . . ? N2 C9 C8 109.4(5) . . ? N2 C9 C13 122.2(5) . . ? C8 C9 C13 128.5(5) . . ? C15 C14 C19 117.4(5) . . ? C15 C14 C1 122.4(5) . . ? C19 C14 C1 120.1(5) . . ? C16 C15 C14 121.1(5) . . ? C15 C16 C17 121.5(5) . . ? C18 C17 C16 117.0(5) . . ? C18 C17 B2 120.9(5) . . ? C16 C17 B2 122.1(5) . . ? C19 C18 C17 122.2(5) . . ? C18 C19 C14 120.6(5) . . ? C21 C20 C25 117.8(5) . . ? C21 C20 B2 121.6(5) . . ? C25 C20 B2 120.6(5) . . ? C22 C21 C20 120.4(5) . . ? C22 C21 C26 118.3(5) . . ? C20 C21 C26 121.2(5) . . ? C21 C22 C23 122.2(6) . . ? C24 C23 C22 116.9(5) . . ? C24 C23 C27 122.1(6) . . ? C22 C23 C27 121.0(6) . . ? C23 C24 C25 122.5(5) . . ? C24 C25 C20 119.9(5) . . ? C24 C25 C28 118.1(5) . . ? C20 C25 C28 122.0(5) . . ? C30 C29 C34 118.2(5) . . ? C30 C29 B2 120.9(5) . . ? C34 C29 B2 120.8(5) . . ? C31 C30 C29 119.9(5) . . ? C31 C30 C36 118.0(5) . . ? C29 C30 C36 122.1(5) . . ? C32 C31 C30 121.8(5) . . ? C31 C32 C33 118.4(6) . . ? C31 C32 C37 121.3(5) . . ? C33 C32 C37 120.3(6) . . ? C32 C33 C34 121.9(6) . . ? C33 C34 C29 119.6(5) . . ? C33 C34 C38 118.4(5) . . ? C29 C34 C38 122.0(5) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.653 _refine_diff_density_min -0.715 _refine_diff_density_rms 0.117 data_1 _database_code_depnum_ccdc_archive 'CCDC 911499' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H27 B O' _chemical_formula_weight 354.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.506(19) _cell_length_b 11.56(3) _cell_length_c 11.58(3) _cell_angle_alpha 83.27(4) _cell_angle_beta 88.36(4) _cell_angle_gamma 76.94(4) _cell_volume 1102(4) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 1407 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 22.21 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.068 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 0.062 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9938 _exptl_absorpt_correction_T_max 0.9950 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker kappa apex ccd' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11674 _diffrn_reflns_av_R_equivalents 0.0623 _diffrn_reflns_av_sigmaI/netI 0.0973 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.74 _reflns_number_total 4855 _reflns_number_gt 2158 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Kappa Apex ccd' _computing_cell_refinement 'bruker saint' _computing_data_reduction 'bruker saint' _computing_structure_solution SHELXS-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ORTEP-III _computing_publication_material WinGXv1.80.05 _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^)+(0.1318P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4855 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1717 _refine_ls_R_factor_gt 0.0839 _refine_ls_wR_factor_ref 0.2562 _refine_ls_wR_factor_gt 0.2055 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.953 _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 B1 B 0.2015(4) 0.2488(3) 0.7895(2) 0.0440(8) Uani 1 1 d . . . C1 C 0.0626(3) 0.3651(2) 0.7543(2) 0.0454(7) Uani 1 1 d . . . C2 C 0.0220(4) 0.4596(3) 0.8260(2) 0.0567(8) Uani 1 1 d . . . H2 H 0.0765 0.4525 0.8959 0.068 Uiso 1 1 calc R . . C3 C -0.0975(4) 0.5630(3) 0.7947(3) 0.0664(9) Uani 1 1 d . . . H3 H -0.1231 0.6225 0.8441 0.080 Uiso 1 1 calc R . . C4 C -0.1779(4) 0.5762(3) 0.6892(3) 0.0588(8) Uani 1 1 d . . . C5 C -0.1413(4) 0.4849(3) 0.6167(3) 0.0615(8) Uani 1 1 d . . . H5 H -0.1958 0.4932 0.5467 0.074 Uiso 1 1 calc R . . C6 C -0.0231(4) 0.3809(3) 0.6490(2) 0.0566(8) Uani 1 1 d . . . H6 H -0.0006 0.3211 0.6000 0.068 Uiso 1 1 calc R . . C7 C -0.3025(5) 0.6894(4) 0.6564(4) 0.0963(13) Uani 1 1 d . . . H7 H -0.3215 0.7478 0.7072 0.116 Uiso 1 1 calc R . . C8 C 0.1907(3) 0.1257(2) 0.7430(2) 0.0469(7) Uani 1 1 d . . . C9 C 0.0447(4) 0.0835(3) 0.7527(3) 0.0581(8) Uani 1 1 d . . . C10 C 0.0328(4) -0.0186(3) 0.7007(3) 0.0675(9) Uani 1 1 d . . . H10 H -0.0637 -0.0439 0.7072 0.081 Uiso 1 1 calc R . . C11 C 0.1605(5) -0.0829(3) 0.6398(3) 0.0675(9) Uani 1 1 d . . . C12 C 0.3047(4) -0.0453(3) 0.6342(2) 0.0639(9) Uani 1 1 d . . . H12 H 0.3916 -0.0880 0.5950 0.077 Uiso 1 1 calc R . . C13 C 0.3245(4) 0.0557(3) 0.6858(2) 0.0502(7) Uani 1 1 d . . . C14 C 0.3446(3) 0.2658(2) 0.8671(2) 0.0470(7) Uani 1 1 d . . . C15 C 0.3782(4) 0.1988(3) 0.9780(2) 0.0525(8) Uani 1 1 d . . . C16 C 0.5025(4) 0.2183(3) 1.0467(2) 0.0606(9) Uani 1 1 d . . . H16 H 0.5224 0.1742 1.1193 0.073 Uiso 1 1 calc R . . C17 C 0.5963(4) 0.3000(3) 1.0113(3) 0.0618(9) Uani 1 1 d . . . C18 C 0.5631(4) 0.3655(3) 0.9027(3) 0.0596(8) Uani 1 1 d . . . H18 H 0.6235 0.4214 0.8772 0.072 Uiso 1 1 calc R . . C19 C 0.4411(3) 0.3501(2) 0.8300(2) 0.0498(7) Uani 1 1 d . . . C20 C -0.1010(4) 0.1438(3) 0.8210(4) 0.0883(12) Uani 1 1 d . . . H20A H -0.1882 0.1798 0.7685 0.132 Uiso 1 1 calc R . . H20B H -0.0724 0.2042 0.8611 0.132 Uiso 1 1 calc R . . H20C H -0.1338 0.0852 0.8764 0.132 Uiso 1 1 calc R . . C21 C 0.1420(6) -0.1920(3) 0.5801(3) 0.1051(14) Uani 1 1 d . . . H21A H 0.2465 -0.2424 0.5693 0.158 Uiso 1 1 calc R . . H21B H 0.0910 -0.1650 0.5059 0.158 Uiso 1 1 calc R . . H21C H 0.0769 -0.2364 0.6279 0.158 Uiso 1 1 calc R . . C22 C 0.4895(4) 0.0882(3) 0.6755(3) 0.0657(9) Uani 1 1 d . . . H22A H 0.5645 0.0280 0.6391 0.099 Uiso 1 1 calc R . . H22B H 0.5279 0.0927 0.7516 0.099 Uiso 1 1 calc R . . H22C H 0.4797 0.1641 0.6295 0.099 Uiso 1 1 calc R . . C23 C 0.2792(4) 0.1095(3) 1.0261(3) 0.0755(10) Uani 1 1 d . . . H23A H 0.3034 0.0855 1.1069 0.113 Uiso 1 1 calc R . . H23B H 0.3053 0.0406 0.9843 0.113 Uiso 1 1 calc R . . H23C H 0.1664 0.1459 1.0173 0.113 Uiso 1 1 calc R . . C24 C 0.7320(4) 0.3173(4) 1.0866(3) 0.0962(13) Uani 1 1 d . . . H24A H 0.6883 0.3738 1.1401 0.144 Uiso 1 1 calc R . . H24B H 0.8109 0.3467 1.0379 0.144 Uiso 1 1 calc R . . H24C H 0.7820 0.2422 1.1291 0.144 Uiso 1 1 calc R . . C25 C 0.4215(4) 0.4204(3) 0.7102(3) 0.0703(9) Uani 1 1 d . . . H25A H 0.3311 0.4873 0.7106 0.105 Uiso 1 1 calc R . . H25B H 0.4035 0.3698 0.6543 0.105 Uiso 1 1 calc R . . H25C H 0.5177 0.4487 0.6901 0.105 Uiso 1 1 calc R . . O1 O -0.3783(5) 0.7080(3) 0.5682(3) 0.1491(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0464(19) 0.0450(19) 0.0437(16) -0.0055(13) 0.0058(14) -0.0171(16) C1 0.0439(17) 0.0448(17) 0.0523(15) -0.0092(12) 0.0000(13) -0.0178(14) C2 0.065(2) 0.0495(19) 0.0577(17) -0.0124(14) -0.0097(14) -0.0131(16) C3 0.075(2) 0.049(2) 0.074(2) -0.0196(16) -0.0030(18) -0.0048(17) C4 0.057(2) 0.0472(19) 0.0691(19) -0.0030(15) 0.0007(16) -0.0067(15) C5 0.057(2) 0.068(2) 0.0567(17) -0.0023(15) -0.0070(15) -0.0100(17) C6 0.0561(19) 0.0538(19) 0.0626(18) -0.0197(14) -0.0044(15) -0.0111(16) C7 0.101(3) 0.091(3) 0.078(2) -0.005(2) -0.013(2) 0.017(2) C8 0.0446(17) 0.0414(16) 0.0539(15) -0.0063(12) -0.0014(13) -0.0073(13) C9 0.054(2) 0.0490(19) 0.077(2) -0.0124(15) -0.0017(16) -0.0199(16) C10 0.066(2) 0.051(2) 0.092(2) -0.0105(18) -0.0141(19) -0.0254(18) C11 0.099(3) 0.0460(19) 0.0610(18) -0.0085(15) -0.0167(18) -0.020(2) C12 0.082(2) 0.050(2) 0.0562(17) -0.0134(14) -0.0023(16) -0.0030(18) C13 0.0582(19) 0.0435(17) 0.0466(15) -0.0053(12) -0.0036(13) -0.0060(14) C14 0.0498(17) 0.0427(16) 0.0499(15) -0.0107(13) 0.0032(13) -0.0105(14) C15 0.061(2) 0.0469(18) 0.0503(16) -0.0065(13) 0.0031(14) -0.0126(15) C16 0.072(2) 0.058(2) 0.0484(16) -0.0073(14) -0.0079(15) -0.0068(18) C17 0.056(2) 0.066(2) 0.0660(19) -0.0247(17) -0.0085(15) -0.0085(17) C18 0.055(2) 0.057(2) 0.073(2) -0.0128(16) -0.0043(16) -0.0237(16) C19 0.0508(18) 0.0465(17) 0.0547(16) -0.0056(13) -0.0036(13) -0.0159(14) C20 0.059(2) 0.072(3) 0.145(3) -0.028(2) 0.023(2) -0.033(2) C21 0.163(4) 0.061(2) 0.102(3) -0.032(2) -0.023(3) -0.033(3) C22 0.057(2) 0.064(2) 0.071(2) -0.0137(16) 0.0047(16) 0.0006(17) C23 0.097(3) 0.069(2) 0.0630(19) 0.0092(16) -0.0031(18) -0.034(2) C24 0.083(3) 0.112(3) 0.100(3) -0.035(2) -0.032(2) -0.020(2) C25 0.072(2) 0.074(2) 0.071(2) 0.0055(17) -0.0020(17) -0.0368(19) O1 0.166(3) 0.122(3) 0.119(2) -0.010(2) -0.033(2) 0.055(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 C14 1.594(5) . ? B1 C1 1.598(5) . ? B1 C8 1.602(5) . ? C1 C6 1.410(4) . ? C1 C2 1.424(5) . ? C2 C3 1.402(5) . ? C3 C4 1.394(5) . ? C4 C5 1.401(5) . ? C4 C7 1.503(6) . ? C5 C6 1.402(5) . ? C7 O1 1.196(5) . ? C8 C9 1.431(5) . ? C8 C13 1.434(4) . ? C9 C10 1.410(5) . ? C9 C20 1.527(5) . ? C10 C11 1.395(5) . ? C11 C12 1.388(5) . ? C11 C21 1.547(5) . ? C12 C13 1.417(5) . ? C13 C22 1.531(5) . ? C14 C15 1.422(5) . ? C14 C19 1.431(4) . ? C15 C16 1.414(5) . ? C15 C23 1.522(5) . ? C16 C17 1.388(5) . ? C17 C18 1.391(5) . ? C17 C24 1.529(5) . ? C18 C19 1.410(4) . ? C19 C25 1.518(5) . ? 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 C14 B1 C1 116.5(3) . . ? C14 B1 C8 124.8(2) . . ? C1 B1 C8 118.7(3) . . ? C6 C1 C2 116.6(3) . . ? C6 C1 B1 121.7(2) . . ? C2 C1 B1 121.7(3) . . ? C3 C2 C1 122.0(3) . . ? C4 C3 C2 119.7(3) . . ? C3 C4 C5 119.7(3) . . ? C3 C4 C7 118.5(3) . . ? C5 C4 C7 121.8(3) . . ? C4 C5 C6 120.4(3) . . ? C5 C6 C1 121.5(3) . . ? O1 C7 C4 123.1(4) . . ? C9 C8 C13 117.2(3) . . ? C9 C8 B1 121.3(3) . . ? C13 C8 B1 121.5(3) . . ? C10 C9 C8 120.3(3) . . ? C10 C9 C20 117.7(3) . . ? C8 C9 C20 122.1(3) . . ? C11 C10 C9 122.4(3) . . ? C12 C11 C10 117.6(3) . . ? C12 C11 C21 121.2(4) . . ? C10 C11 C21 121.2(4) . . ? C11 C12 C13 122.5(3) . . ? C12 C13 C8 119.8(3) . . ? C12 C13 C22 118.1(3) . . ? C8 C13 C22 122.1(3) . . ? C15 C14 C19 117.5(3) . . ? C15 C14 B1 120.5(3) . . ? C19 C14 B1 121.9(3) . . ? C16 C15 C14 119.4(3) . . ? C16 C15 C23 119.3(3) . . ? C14 C15 C23 121.2(3) . . ? C17 C16 C15 123.3(3) . . ? C16 C17 C18 117.2(3) . . ? C16 C17 C24 122.1(3) . . ? C18 C17 C24 120.7(3) . . ? C17 C18 C19 122.2(3) . . ? C18 C19 C14 120.4(3) . . ? C18 C19 C25 118.0(3) . . ? C14 C19 C25 121.5(3) . . ? _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 27.74 _diffrn_measured_fraction_theta_full 0.936 _refine_diff_density_max 0.403 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.060 data_2 _database_code_depnum_ccdc_archive 'CCDC 911500' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H36 B2 F2 N2' _chemical_formula_weight 544.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pca2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 36.823(8) _cell_length_b 8.3144(17) _cell_length_c 9.7870(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2996.4(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2319 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 17.08 _exptl_crystal_description PRISM _exptl_crystal_colour RED _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.207 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9908 _exptl_absorpt_correction_T_max 0.9923 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker kappa apex ccd' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 62836 _diffrn_reflns_av_R_equivalents 0.1748 _diffrn_reflns_av_sigmaI/netI 0.1841 _diffrn_reflns_limit_h_min -52 _diffrn_reflns_limit_h_max 51 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 30.66 _reflns_number_total 8945 _reflns_number_gt 3776 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Kappa Apex ccd' _computing_cell_refinement 'bruker saint' _computing_data_reduction 'bruker saint' _computing_structure_solution SHELXS-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ORTEP-III _computing_publication_material WinGXv1.80.05 _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^)+(0.0576P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(11) _refine_ls_number_reflns 8945 _refine_ls_number_parameters 378 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.2095 _refine_ls_R_factor_gt 0.0695 _refine_ls_wR_factor_ref 0.1538 _refine_ls_wR_factor_gt 0.1138 _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_restrained_S_all 0.960 _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 B1 B 0.16828(12) 0.5007(5) 0.2186(4) 0.0397(11) Uani 1 1 d . . . B2 B 0.39591(9) 0.8348(4) 0.2630(4) 0.0262(8) Uani 1 1 d . . . F1 F 0.13942(5) 0.5057(3) 0.1290(2) 0.0519(6) Uani 1 1 d . . . F2 F 0.15742(6) 0.4242(3) 0.3387(2) 0.0622(7) Uani 1 1 d . . . N1 N 0.18173(7) 0.6709(3) 0.2529(3) 0.0315(6) Uani 1 1 d . . . N2 N 0.20077(7) 0.4089(3) 0.1567(3) 0.0368(7) Uani 1 1 d . . . C1 C 0.16199(9) 0.8030(5) 0.2865(4) 0.0408(9) Uani 1 1 d . . . C2 C 0.18533(10) 0.9301(5) 0.3205(3) 0.0446(10) Uani 1 1 d . . . H2 H 0.1784 1.0328 0.3479 0.054 Uiso 1 1 calc R . . C3 C 0.22044(10) 0.8748(4) 0.3061(3) 0.0372(9) Uani 1 1 d . . . H3 H 0.2415 0.9336 0.3214 0.045 Uiso 1 1 calc R . . C4 C 0.21859(8) 0.7116(4) 0.2634(3) 0.0280(7) Uani 1 1 d . . . C5 C 0.24579(9) 0.6054(4) 0.2270(3) 0.0281(8) Uani 1 1 d . . . C6 C 0.23710(9) 0.4562(4) 0.1704(3) 0.0313(8) Uani 1 1 d . . . C7 C 0.25877(10) 0.3323(4) 0.1153(4) 0.0498(10) Uani 1 1 d . . . H7 H 0.2840 0.3301 0.1116 0.060 Uiso 1 1 calc R . . C8 C 0.23546(12) 0.2153(5) 0.0681(5) 0.0609(12) Uani 1 1 d . . . H8 H 0.2422 0.1200 0.0253 0.073 Uiso 1 1 calc R . . C9 C 0.19996(11) 0.2642(5) 0.0954(4) 0.0514(11) Uani 1 1 d . . . C10 C 0.28422(8) 0.6552(4) 0.2389(3) 0.0272(7) Uani 1 1 d . . . C11 C 0.29908(8) 0.6937(4) 0.3645(3) 0.0273(8) Uani 1 1 d . . . H11 H 0.2850 0.6862 0.4430 0.033 Uiso 1 1 calc R . . C12 C 0.33482(9) 0.7434(4) 0.3737(3) 0.0281(8) Uani 1 1 d . . . H12 H 0.3448 0.7629 0.4593 0.034 Uiso 1 1 calc R . . C13 C 0.35637(8) 0.7651(3) 0.2566(3) 0.0278(7) Uani 1 1 d . . . C14 C 0.34077(9) 0.7240(4) 0.1330(3) 0.0381(9) Uani 1 1 d . . . H14 H 0.3544 0.7360 0.0536 0.046 Uiso 1 1 calc R . . C15 C 0.30589(8) 0.6662(4) 0.1230(3) 0.0377(9) Uani 1 1 d . . . H15 H 0.2968 0.6344 0.0386 0.045 Uiso 1 1 calc R . . C16 C 0.40895(8) 0.9474(3) 0.1447(3) 0.0264(7) Uani 1 1 d . . . C17 C 0.38893(8) 1.0872(4) 0.1098(3) 0.0304(7) Uani 1 1 d . . . C18 C 0.40169(10) 1.1907(4) 0.0089(3) 0.0359(8) Uani 1 1 d . . . H18 H 0.3883 1.2826 -0.0116 0.043 Uiso 1 1 calc R . . C19 C 0.43314(10) 1.1622(4) -0.0612(3) 0.0349(8) Uani 1 1 d . . . C20 C 0.45222(9) 1.0215(4) -0.0314(3) 0.0349(8) Uani 1 1 d . . . H20 H 0.4730 0.9969 -0.0813 0.042 Uiso 1 1 calc R . . C21 C 0.44081(8) 0.9167(4) 0.0716(3) 0.0280(7) Uani 1 1 d . . . C22 C 0.42125(8) 0.7876(4) 0.3858(3) 0.0232(7) Uani 1 1 d . . . C23 C 0.43923(8) 0.9039(3) 0.4655(3) 0.0246(7) Uani 1 1 d . . . C24 C 0.46259(8) 0.8582(4) 0.5693(3) 0.0264(7) Uani 1 1 d . . . H24 H 0.4734 0.9372 0.6230 0.032 Uiso 1 1 calc R . . C25 C 0.47043(8) 0.6975(4) 0.5955(3) 0.0277(7) Uani 1 1 d . . . C26 C 0.45289(8) 0.5819(4) 0.5178(3) 0.0287(8) Uani 1 1 d . . . H26 H 0.4577 0.4739 0.5343 0.034 Uiso 1 1 calc R . . C27 C 0.42817(8) 0.6228(3) 0.4152(3) 0.0254(7) Uani 1 1 d . . . C28 C 0.12120(9) 0.8031(5) 0.2830(4) 0.0539(11) Uani 1 1 d . . . H28A H 0.1131 0.8114 0.1901 0.081 Uiso 1 1 calc R . . H28B H 0.1122 0.8929 0.3345 0.081 Uiso 1 1 calc R . . H28C H 0.1123 0.7049 0.3223 0.081 Uiso 1 1 calc R . . C29 C 0.16523(13) 0.1799(5) 0.0619(5) 0.0726(15) Uani 1 1 d . . . H29A H 0.1503 0.1746 0.1420 0.109 Uiso 1 1 calc R . . H29B H 0.1705 0.0730 0.0305 0.109 Uiso 1 1 calc R . . H29C H 0.1527 0.2380 -0.0085 0.109 Uiso 1 1 calc R . . C30 C 0.35359(9) 1.1322(4) 0.1796(4) 0.0427(9) Uani 1 1 d . . . H30A H 0.3497 1.2459 0.1712 0.064 Uiso 1 1 calc R . . H30B H 0.3549 1.1037 0.2745 0.064 Uiso 1 1 calc R . . H30C H 0.3339 1.0754 0.1372 0.064 Uiso 1 1 calc R . . C31 C 0.44677(11) 1.2785(5) -0.1662(4) 0.0541(11) Uani 1 1 d . . . H31A H 0.4513 1.2225 -0.2503 0.081 Uiso 1 1 calc R . . H31B H 0.4689 1.3269 -0.1346 0.081 Uiso 1 1 calc R . . H31C H 0.4289 1.3606 -0.1812 0.081 Uiso 1 1 calc R . . C32 C 0.46290(9) 0.7665(4) 0.0961(4) 0.0433(9) Uani 1 1 d . . . H32A H 0.4700 0.7617 0.1903 0.065 Uiso 1 1 calc R . . H32B H 0.4842 0.7685 0.0393 0.065 Uiso 1 1 calc R . . H32C H 0.4486 0.6736 0.0740 0.065 Uiso 1 1 calc R . . C33 C 0.43273(9) 1.0812(3) 0.4422(3) 0.0349(8) Uani 1 1 d . . . H33A H 0.4476 1.1425 0.5035 0.052 Uiso 1 1 calc R . . H33B H 0.4076 1.1055 0.4586 0.052 Uiso 1 1 calc R . . H33C H 0.4388 1.1081 0.3496 0.052 Uiso 1 1 calc R . . C34 C 0.49790(10) 0.6530(4) 0.7023(4) 0.0418(9) Uani 1 1 d . . . H34A H 0.5216 0.6867 0.6731 0.063 Uiso 1 1 calc R . . H34B H 0.4978 0.5386 0.7154 0.063 Uiso 1 1 calc R . . H34C H 0.4919 0.7053 0.7868 0.063 Uiso 1 1 calc R . . C35 C 0.41021(9) 0.4882(3) 0.3367(3) 0.0328(8) Uani 1 1 d . . . H35A H 0.3870 0.4646 0.3766 0.049 Uiso 1 1 calc R . . H35B H 0.4253 0.3940 0.3402 0.049 Uiso 1 1 calc R . . H35C H 0.4069 0.5203 0.2432 0.049 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 B1 0.035(3) 0.057(3) 0.027(2) 0.009(2) -0.0071(19) -0.009(2) B2 0.024(2) 0.0241(18) 0.031(2) -0.0008(17) -0.0013(18) 0.0064(15) F1 0.0319(11) 0.0725(14) 0.0514(12) 0.0069(12) -0.0152(10) -0.0150(10) F2 0.0591(15) 0.0815(16) 0.0462(13) 0.0250(12) 0.0018(12) -0.0281(13) N1 0.0242(15) 0.0498(17) 0.0204(13) 0.0038(14) 0.0021(13) -0.0039(13) N2 0.0388(18) 0.0383(17) 0.0333(16) 0.0047(14) -0.0091(14) -0.0090(14) C1 0.029(2) 0.067(3) 0.0269(19) 0.0061(18) -0.0002(16) 0.010(2) C2 0.049(3) 0.049(2) 0.036(2) 0.0004(18) -0.0044(18) 0.012(2) C3 0.037(2) 0.040(2) 0.034(2) 0.0045(16) 0.0001(16) 0.0006(17) C4 0.0188(18) 0.0382(19) 0.0271(18) 0.0012(16) 0.0014(15) -0.0037(15) C5 0.027(2) 0.0382(19) 0.0195(17) 0.0048(15) 0.0008(14) -0.0057(15) C6 0.029(2) 0.0346(19) 0.0301(19) 0.0059(16) -0.0028(15) -0.0010(15) C7 0.045(2) 0.054(2) 0.050(2) -0.006(2) -0.010(2) 0.008(2) C8 0.070(3) 0.043(2) 0.070(3) -0.017(2) -0.021(2) 0.009(2) C9 0.059(3) 0.043(2) 0.052(3) 0.003(2) -0.022(2) -0.010(2) C10 0.0222(18) 0.0330(17) 0.0264(18) 0.0019(15) -0.0047(15) -0.0017(14) C11 0.0225(18) 0.0358(18) 0.0234(18) 0.0050(15) 0.0058(15) -0.0018(15) C12 0.027(2) 0.0361(18) 0.0211(17) 0.0019(14) -0.0043(15) -0.0005(15) C13 0.0265(18) 0.0340(17) 0.0228(17) 0.0052(15) 0.0017(16) 0.0000(14) C14 0.0219(19) 0.067(2) 0.0257(19) 0.0038(18) 0.0028(16) -0.0055(17) C15 0.027(2) 0.063(2) 0.0232(19) 0.0000(17) -0.0015(16) -0.0103(17) C16 0.0232(18) 0.0271(16) 0.0288(18) 0.0077(14) -0.0074(15) -0.0011(13) C17 0.0278(18) 0.0325(17) 0.0309(19) 0.0014(16) -0.0037(15) 0.0006(15) C18 0.043(2) 0.0328(19) 0.0320(19) 0.0101(16) -0.0089(18) -0.0024(17) C19 0.042(2) 0.0347(18) 0.0283(18) 0.0073(16) -0.0060(17) -0.0125(16) C20 0.0258(19) 0.047(2) 0.0314(19) 0.0057(17) 0.0035(16) -0.0074(16) C21 0.0213(18) 0.0336(18) 0.0293(17) 0.0077(15) -0.0029(15) -0.0041(14) C22 0.0143(16) 0.0258(16) 0.0295(18) 0.0059(14) 0.0024(13) 0.0005(13) C23 0.0213(17) 0.0215(15) 0.0309(18) 0.0035(14) 0.0036(15) 0.0000(13) C24 0.0252(18) 0.0265(17) 0.0274(17) 0.0025(14) -0.0003(15) -0.0045(14) C25 0.0216(17) 0.0334(18) 0.0281(18) 0.0070(15) 0.0003(15) 0.0009(14) C26 0.0300(19) 0.0232(16) 0.0328(18) 0.0078(15) 0.0005(15) 0.0034(15) C27 0.0211(17) 0.0264(17) 0.0287(17) 0.0037(14) 0.0038(14) -0.0007(13) C28 0.030(2) 0.095(3) 0.037(2) 0.000(2) -0.0013(19) 0.014(2) C29 0.092(4) 0.050(3) 0.075(3) 0.008(2) -0.045(3) -0.030(2) C30 0.040(2) 0.040(2) 0.048(2) 0.0075(18) -0.0021(18) 0.0108(17) C31 0.062(3) 0.057(2) 0.043(2) 0.019(2) 0.000(2) -0.018(2) C32 0.030(2) 0.056(2) 0.044(2) 0.0110(19) 0.0069(18) 0.0090(17) C33 0.041(2) 0.0250(16) 0.038(2) 0.0029(16) -0.0054(17) 0.0016(15) C34 0.048(2) 0.040(2) 0.037(2) 0.0079(17) -0.0158(17) 0.0046(17) C35 0.037(2) 0.0206(16) 0.041(2) 0.0000(15) -0.0020(17) -0.0016(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 F1 1.378(4) . ? B1 F2 1.395(4) . ? B1 N1 1.536(5) . ? B1 N2 1.543(5) . ? B2 C16 1.564(5) . ? B2 C13 1.568(4) . ? B2 C22 1.571(5) . ? N1 C1 1.358(4) . ? N1 C4 1.403(4) . ? N2 C9 1.344(4) . ? N2 C6 1.401(4) . ? C1 C2 1.402(5) . ? C1 C28 1.502(5) . ? C2 C3 1.379(5) . ? C3 C4 1.421(5) . ? C4 C5 1.382(4) . ? C5 C6 1.396(4) . ? C5 C10 1.479(4) . ? C6 C7 1.410(5) . ? C7 C8 1.377(5) . ? C8 C9 1.395(5) . ? C9 C29 1.495(5) . ? C10 C11 1.383(4) . ? C10 C15 1.390(4) . ? C11 C12 1.382(4) . ? C12 C13 1.405(4) . ? C13 C14 1.382(4) . ? C14 C15 1.375(4) . ? C16 C21 1.398(4) . ? C16 C17 1.418(4) . ? C17 C18 1.392(4) . ? C17 C30 1.517(4) . ? C18 C19 1.367(5) . ? C19 C20 1.396(4) . ? C19 C31 1.498(5) . ? C20 C21 1.397(4) . ? C21 C32 1.510(4) . ? C22 C23 1.408(4) . ? C22 C27 1.423(4) . ? C23 C24 1.384(4) . ? C23 C33 1.511(4) . ? C24 C25 1.391(4) . ? C25 C26 1.385(4) . ? C25 C34 1.501(4) . ? C26 C27 1.397(4) . ? C27 C35 1.510(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 F1 B1 F2 109.2(3) . . ? F1 B1 N1 111.1(3) . . ? F2 B1 N1 109.2(3) . . ? F1 B1 N2 111.3(3) . . ? F2 B1 N2 109.1(3) . . ? N1 B1 N2 107.0(3) . . ? C16 B2 C13 118.5(3) . . ? C16 B2 C22 122.2(3) . . ? C13 B2 C22 119.3(3) . . ? C1 N1 C4 107.7(3) . . ? C1 N1 B1 128.7(3) . . ? C4 N1 B1 123.4(3) . . ? C9 N2 C6 108.4(3) . . ? C9 N2 B1 126.9(3) . . ? C6 N2 B1 124.3(3) . . ? N1 C1 C2 109.8(3) . . ? N1 C1 C28 122.0(3) . . ? C2 C1 C28 128.2(3) . . ? C3 C2 C1 107.4(3) . . ? C2 C3 C4 107.7(3) . . ? C5 C4 N1 121.9(3) . . ? C5 C4 C3 130.6(3) . . ? N1 C4 C3 107.4(3) . . ? C4 C5 C6 120.3(3) . . ? C4 C5 C10 119.6(3) . . ? C6 C5 C10 120.0(3) . . ? C5 C6 N2 120.4(3) . . ? C5 C6 C7 132.1(3) . . ? N2 C6 C7 107.4(3) . . ? C8 C7 C6 107.0(3) . . ? C7 C8 C9 108.3(4) . . ? N2 C9 C8 109.0(3) . . ? N2 C9 C29 122.5(4) . . ? C8 C9 C29 128.5(4) . . ? C11 C10 C15 118.9(3) . . ? C11 C10 C5 120.9(3) . . ? C15 C10 C5 120.3(3) . . ? C12 C11 C10 120.2(3) . . ? C11 C12 C13 121.5(3) . . ? C14 C13 C12 116.6(3) . . ? C14 C13 B2 120.8(3) . . ? C12 C13 B2 122.6(3) . . ? C15 C14 C13 122.5(3) . . ? C14 C15 C10 120.1(3) . . ? C21 C16 C17 117.6(3) . . ? C21 C16 B2 121.8(3) . . ? C17 C16 B2 120.6(3) . . ? C18 C17 C16 120.2(3) . . ? C18 C17 C30 117.2(3) . . ? C16 C17 C30 122.7(3) . . ? C19 C18 C17 122.3(3) . . ? C18 C19 C20 117.9(3) . . ? C18 C19 C31 121.1(3) . . ? C20 C19 C31 121.0(3) . . ? C19 C20 C21 121.5(3) . . ? C20 C21 C16 120.5(3) . . ? C20 C21 C32 117.9(3) . . ? C16 C21 C32 121.5(3) . . ? C23 C22 C27 117.7(3) . . ? C23 C22 B2 122.2(3) . . ? C27 C22 B2 120.1(3) . . ? C24 C23 C22 120.7(3) . . ? C24 C23 C33 118.5(3) . . ? C22 C23 C33 120.8(3) . . ? C23 C24 C25 121.8(3) . . ? C26 C25 C24 117.9(3) . . ? C26 C25 C34 121.7(3) . . ? C24 C25 C34 120.3(3) . . ? C25 C26 C27 122.0(3) . . ? C26 C27 C22 119.8(3) . . ? C26 C27 C35 118.1(3) . . ? C22 C27 C35 122.1(3) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 30.66 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.241 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.057