# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email dstephan@chem.utoronto.ca _publ_contact_author_name 'Douglas Stephan' loop_ _publ_author_name 'Christopher Caputo' 'Stephen Geier' 'Daniel Winkelhaus' 'Norbert Mitzel' 'Stephen Loeb' 'Nicholas Vukotic' 'Douglas Stephan' data_dw002_0m _database_code_depnum_ccdc_archive 'CCDC 846344' #TrackingRef '- 1-dw002_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H22 B2 F15 N O2' _chemical_formula_weight 747.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.8926(6) _cell_length_b 11.0691(5) _cell_length_c 14.3170(8) _cell_angle_alpha 99.984(2) _cell_angle_beta 109.274(2) _cell_angle_gamma 95.546(2) _cell_volume 1582.65(14) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7200 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7159 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26474 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0479 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 27.56 _reflns_number_total 7200 _reflns_number_gt 4456 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0785P)^2^+0.8566P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7200 _refine_ls_number_parameters 464 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0923 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1476 _refine_ls_wR_factor_gt 0.1221 _refine_ls_goodness_of_fit_ref 0.905 _refine_ls_restrained_S_all 0.905 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.74400(18) 0.29598(18) 0.07815(14) 0.0327(5) Uani 1 1 d . . . H1A H 0.6914 0.2370 0.0271 0.039 Uiso 1 1 calc R . . O1 O 1.12636(17) 0.61866(18) 0.34008(14) 0.0502(5) Uani 1 1 d . . . O2 O 0.95254(16) 0.65305(16) 0.38908(14) 0.0444(5) Uani 1 1 d . . . B1 B 0.5043(2) 0.8447(2) 0.18543(19) 0.0268(5) Uani 1 1 d . . . B2 B 0.9977(3) 0.5873(3) 0.3234(2) 0.0343(6) Uani 1 1 d . . . F1 F 0.67654(13) 1.10156(12) 0.24471(11) 0.0430(4) Uani 1 1 d . . . F2 F 0.91111(14) 1.14428(14) 0.22772(12) 0.0502(4) Uani 1 1 d . . . F3 F 1.02060(15) 0.95523(16) 0.15708(13) 0.0552(4) Uani 1 1 d . . . F4 F 0.89015(16) 0.71687(15) 0.10825(14) 0.0571(5) Uani 1 1 d . . . F5 F 0.65330(14) 0.67111(12) 0.12166(11) 0.0428(4) Uani 1 1 d . . . F6 F 0.70453(13) 0.82303(13) 0.38163(10) 0.0396(3) Uani 1 1 d . . . F7 F 0.69790(16) 0.63112(15) 0.47232(11) 0.0523(4) Uani 1 1 d . . . F8 F 0.49060(19) 0.43953(15) 0.39136(14) 0.0649(5) Uani 1 1 d . . . F9 F 0.29158(17) 0.44316(14) 0.21840(15) 0.0624(5) Uani 1 1 d . . . F10 F 0.29475(14) 0.63278(13) 0.12895(12) 0.0483(4) Uani 1 1 d . . . F11 F 0.35294(15) 0.98185(14) 0.04359(10) 0.0441(4) Uani 1 1 d . . . F12 F 0.21232(16) 1.15527(15) 0.08205(12) 0.0541(4) Uani 1 1 d . . . F13 F 0.20787(14) 1.23032(13) 0.27223(12) 0.0457(4) Uani 1 1 d . . . F14 F 0.35855(16) 1.13508(13) 0.42550(11) 0.0468(4) Uani 1 1 d . . . F15 F 0.50110(15) 0.96307(13) 0.38960(10) 0.0427(4) Uani 1 1 d . . . C1 C 0.6520(2) 0.8834(2) 0.18444(16) 0.0271(5) Uani 1 1 d . . . C2 C 0.7247(2) 1.0011(2) 0.21007(17) 0.0305(5) Uani 1 1 d . . . C3 C 0.8467(2) 1.0270(2) 0.20210(18) 0.0354(6) Uani 1 1 d . . . C4 C 0.9027(2) 0.9316(3) 0.1667(2) 0.0389(6) Uani 1 1 d . . . C5 C 0.8364(3) 0.8117(2) 0.14136(19) 0.0384(6) Uani 1 1 d . . . C6 C 0.7144(2) 0.7913(2) 0.15028(18) 0.0319(5) Uani 1 1 d . . . C7 C 0.5007(2) 0.7379(2) 0.25037(17) 0.0284(5) Uani 1 1 d . . . C8 C 0.5991(2) 0.7310(2) 0.33877(17) 0.0298(5) Uani 1 1 d . . . C9 C 0.5982(3) 0.6334(2) 0.38764(18) 0.0374(6) Uani 1 1 d . . . C10 C 0.4939(3) 0.5361(2) 0.3470(2) 0.0424(6) Uani 1 1 d . . . C11 C 0.3928(3) 0.5391(2) 0.2600(2) 0.0413(6) Uani 1 1 d . . . C12 C 0.3977(2) 0.6376(2) 0.21488(19) 0.0342(5) Uani 1 1 d . . . C13 C 0.4316(2) 0.9599(2) 0.21442(16) 0.0265(5) Uani 1 1 d . . . C14 C 0.3569(2) 1.0161(2) 0.14119(17) 0.0297(5) Uani 1 1 d . . . C15 C 0.2842(2) 1.1067(2) 0.15845(18) 0.0338(5) Uani 1 1 d . . . C16 C 0.2831(2) 1.1466(2) 0.25467(19) 0.0319(5) Uani 1 1 d . . . C17 C 0.3578(2) 1.0972(2) 0.33118(17) 0.0307(5) Uani 1 1 d . . . C18 C 0.4298(2) 1.0064(2) 0.31023(17) 0.0294(5) Uani 1 1 d . . . C19 C 0.8721(2) 0.3173(2) 0.08814(18) 0.0331(5) Uani 1 1 d . . . C20 C 0.9534(2) 0.4118(2) 0.16637(18) 0.0338(5) Uani 1 1 d . . . H20A H 1.0439 0.4305 0.1749 0.041 Uiso 1 1 calc R . . C21 C 0.9048(2) 0.4800(2) 0.23296(17) 0.0313(5) Uani 1 1 d . . . C22 C 0.7720(2) 0.4512(2) 0.21913(17) 0.0322(5) Uani 1 1 d . . . H22A H 0.7376 0.4966 0.2647 0.039 Uiso 1 1 calc R . . C23 C 0.6900(2) 0.3580(2) 0.14041(18) 0.0325(5) Uani 1 1 d . . . C24 C 0.9152(3) 0.2363(3) 0.0144(2) 0.0471(7) Uani 1 1 d . . . H24A H 0.8389 0.1775 -0.0348 0.071 Uiso 1 1 calc R . . H24B H 0.9810 0.1902 0.0507 0.071 Uiso 1 1 calc R . . H24C H 0.9540 0.2878 -0.0212 0.071 Uiso 1 1 calc R . . C25 C 0.5463(2) 0.3205(3) 0.1183(2) 0.0460(7) Uani 1 1 d . . . H25A H 0.5100 0.2519 0.0584 0.069 Uiso 1 1 calc R . . H25B H 0.5009 0.3915 0.1053 0.069 Uiso 1 1 calc R . . H25C H 0.5335 0.2936 0.1766 0.069 Uiso 1 1 calc R . . C26 C 1.1729(3) 0.7338(2) 0.4198(2) 0.0459(7) Uani 1 1 d . . . C27 C 1.3118(3) 0.7332(4) 0.4861(3) 0.0833(13) Uani 1 1 d . . . H27A H 1.3137 0.6634 0.5200 0.125 Uiso 1 1 calc R . . H27B H 1.3451 0.8115 0.5371 0.125 Uiso 1 1 calc R . . H27C H 1.3674 0.7243 0.4445 0.125 Uiso 1 1 calc R . . C28 C 1.1679(4) 0.8397(3) 0.3641(3) 0.0867(13) Uani 1 1 d . . . H28A H 1.0765 0.8393 0.3216 0.130 Uiso 1 1 calc R . . H28B H 1.2220 0.8288 0.3215 0.130 Uiso 1 1 calc R . . H28C H 1.2021 0.9192 0.4136 0.130 Uiso 1 1 calc R . . C29 C 1.0696(3) 0.7282(2) 0.4714(2) 0.0407(6) Uani 1 1 d . . . C30 C 1.1017(4) 0.6567(3) 0.5552(2) 0.0762(12) Uani 1 1 d . . . H30B H 1.0323 0.6564 0.5846 0.114 Uiso 1 1 calc R . . H30C H 1.1864 0.6964 0.6079 0.114 Uiso 1 1 calc R . . H30D H 1.1073 0.5709 0.5273 0.114 Uiso 1 1 calc R . . C31 C 1.0342(3) 0.8516(3) 0.5077(3) 0.0675(10) Uani 1 1 d . . . H31C H 1.0130 0.8967 0.4527 0.101 Uiso 1 1 calc R . . H31D H 1.1091 0.9007 0.5657 0.101 Uiso 1 1 calc R . . H31A H 0.9576 0.8376 0.5282 0.101 Uiso 1 1 calc R . . H1 H 0.442(2) 0.797(2) 0.1031(17) 0.029(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0251(10) 0.0389(11) 0.0256(10) -0.0053(8) 0.0055(8) 0.0005(8) O1 0.0329(10) 0.0545(12) 0.0465(11) -0.0127(9) 0.0078(8) -0.0049(8) O2 0.0337(10) 0.0379(10) 0.0470(11) -0.0117(8) 0.0091(8) -0.0054(8) B1 0.0256(13) 0.0270(13) 0.0243(13) 0.0025(10) 0.0064(10) 0.0021(10) B2 0.0338(15) 0.0311(14) 0.0330(15) 0.0072(12) 0.0059(12) 0.0027(12) F1 0.0376(8) 0.0289(7) 0.0590(10) -0.0024(7) 0.0202(7) -0.0002(6) F2 0.0421(9) 0.0430(9) 0.0635(10) 0.0090(8) 0.0219(8) -0.0095(7) F3 0.0400(9) 0.0677(11) 0.0708(11) 0.0205(9) 0.0346(8) 0.0061(8) F4 0.0603(10) 0.0514(10) 0.0829(12) 0.0173(9) 0.0503(10) 0.0235(8) F5 0.0486(9) 0.0282(7) 0.0568(9) 0.0046(7) 0.0275(7) 0.0066(6) F6 0.0313(7) 0.0490(8) 0.0329(8) 0.0081(6) 0.0054(6) 0.0032(6) F7 0.0589(10) 0.0654(10) 0.0419(9) 0.0254(8) 0.0175(8) 0.0308(8) F8 0.0902(14) 0.0456(10) 0.0795(13) 0.0370(9) 0.0418(11) 0.0226(9) F9 0.0621(11) 0.0340(8) 0.0885(13) 0.0129(8) 0.0286(10) -0.0097(8) F10 0.0342(8) 0.0439(9) 0.0521(9) 0.0092(7) 0.0006(7) -0.0076(7) F11 0.0539(9) 0.0533(9) 0.0275(8) 0.0133(7) 0.0124(7) 0.0193(7) F12 0.0558(10) 0.0616(10) 0.0476(9) 0.0239(8) 0.0102(8) 0.0300(8) F13 0.0431(8) 0.0347(8) 0.0669(10) 0.0111(7) 0.0264(8) 0.0162(7) F14 0.0678(10) 0.0392(8) 0.0390(8) 0.0032(7) 0.0271(8) 0.0157(7) F15 0.0602(10) 0.0396(8) 0.0259(7) 0.0069(6) 0.0089(7) 0.0198(7) C1 0.0290(12) 0.0311(12) 0.0206(11) 0.0071(9) 0.0070(9) 0.0053(9) C2 0.0313(12) 0.0307(12) 0.0301(12) 0.0066(10) 0.0115(10) 0.0058(10) C3 0.0313(13) 0.0375(14) 0.0353(13) 0.0100(11) 0.0104(11) -0.0035(10) C4 0.0296(13) 0.0535(16) 0.0414(14) 0.0171(12) 0.0195(11) 0.0057(11) C5 0.0427(15) 0.0427(15) 0.0410(14) 0.0138(12) 0.0243(12) 0.0168(12) C6 0.0333(13) 0.0311(13) 0.0328(13) 0.0083(10) 0.0140(10) 0.0024(10) C7 0.0296(12) 0.0266(11) 0.0304(12) 0.0033(9) 0.0133(10) 0.0060(9) C8 0.0295(12) 0.0307(12) 0.0324(13) 0.0042(10) 0.0158(10) 0.0073(10) C9 0.0432(15) 0.0449(15) 0.0311(13) 0.0124(11) 0.0158(11) 0.0225(12) C10 0.0597(18) 0.0287(13) 0.0555(17) 0.0184(12) 0.0344(15) 0.0174(12) C11 0.0422(15) 0.0279(13) 0.0570(17) 0.0072(12) 0.0237(13) 0.0025(11) C12 0.0308(13) 0.0334(13) 0.0387(14) 0.0067(11) 0.0133(11) 0.0053(10) C13 0.0225(11) 0.0257(11) 0.0289(12) 0.0045(9) 0.0078(9) -0.0002(9) C14 0.0273(12) 0.0322(12) 0.0268(12) 0.0050(10) 0.0077(9) 0.0015(9) C15 0.0267(12) 0.0344(13) 0.0378(14) 0.0139(11) 0.0048(10) 0.0059(10) C16 0.0268(12) 0.0220(11) 0.0484(15) 0.0059(10) 0.0163(11) 0.0034(9) C17 0.0352(13) 0.0262(12) 0.0310(13) 0.0016(10) 0.0161(10) -0.0008(10) C18 0.0320(12) 0.0248(11) 0.0294(12) 0.0062(9) 0.0088(10) 0.0020(9) C19 0.0275(12) 0.0402(14) 0.0294(12) 0.0023(10) 0.0096(10) 0.0065(10) C20 0.0239(12) 0.0424(14) 0.0308(13) 0.0054(11) 0.0066(10) 0.0019(10) C21 0.0289(12) 0.0306(12) 0.0283(12) 0.0041(10) 0.0043(10) 0.0011(10) C22 0.0332(13) 0.0316(12) 0.0287(12) 0.0008(10) 0.0099(10) 0.0055(10) C23 0.0291(12) 0.0362(13) 0.0310(12) 0.0036(10) 0.0104(10) 0.0069(10) C24 0.0370(15) 0.0623(18) 0.0394(15) -0.0031(13) 0.0165(12) 0.0108(13) C25 0.0286(13) 0.0568(17) 0.0449(15) -0.0079(13) 0.0143(12) 0.0007(12) C26 0.0353(14) 0.0400(15) 0.0453(16) -0.0042(12) 0.0025(12) -0.0069(12) C27 0.0391(18) 0.088(3) 0.080(3) -0.029(2) -0.0096(17) 0.0043(17) C28 0.104(3) 0.069(2) 0.064(2) 0.0169(19) 0.015(2) -0.043(2) C29 0.0388(14) 0.0271(12) 0.0400(15) -0.0052(11) 0.0020(11) -0.0056(11) C30 0.119(3) 0.0446(18) 0.0386(17) 0.0017(14) 0.0077(18) -0.0223(19) C31 0.0560(19) 0.0398(16) 0.077(2) -0.0218(16) 0.0029(17) 0.0027(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 N1 C19 1.348(3) . ? N1 C23 1.351(3) . ? O1 B2 1.340(3) . ? O1 C26 1.474(3) . ? O2 B2 1.339(3) . ? O2 C29 1.473(3) . ? B1 C13 1.629(3) . ? B1 C1 1.630(3) . ? B1 C7 1.631(3) . ? B2 C21 1.575(4) . ? F1 C2 1.360(3) . ? F2 C3 1.342(3) . ? F3 C4 1.342(3) . ? F4 C5 1.341(3) . ? F5 C6 1.357(3) . ? F6 C8 1.351(3) . ? F7 C9 1.340(3) . ? F8 C10 1.338(3) . ? F9 C11 1.348(3) . ? F10 C12 1.352(3) . ? F11 C14 1.368(3) . ? F12 C15 1.349(3) . ? F13 C16 1.340(3) . ? F14 C17 1.340(3) . ? F15 C18 1.343(3) . ? C1 C2 1.379(3) . ? C1 C6 1.386(3) . ? C2 C3 1.378(3) . ? C3 C4 1.373(4) . ? C4 C5 1.375(4) . ? C5 C6 1.377(3) . ? C7 C8 1.382(3) . ? C7 C12 1.391(3) . ? C8 C9 1.387(3) . ? C9 C10 1.378(4) . ? C10 C11 1.371(4) . ? C11 C12 1.366(4) . ? C13 C14 1.382(3) . ? C13 C18 1.387(3) . ? C14 C15 1.375(3) . ? C15 C16 1.376(3) . ? C16 C17 1.366(3) . ? C17 C18 1.384(3) . ? C19 C20 1.375(3) . ? C19 C24 1.489(3) . ? C20 C21 1.386(3) . ? C21 C22 1.390(3) . ? C22 C23 1.374(3) . ? C23 C25 1.491(3) . ? C26 C27 1.499(4) . ? C26 C28 1.523(4) . ? C26 C29 1.539(4) . ? C29 C31 1.507(4) . ? C29 C30 1.515(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 C19 N1 C23 125.1(2) . . ? B2 O1 C26 106.1(2) . . ? B2 O2 C29 106.1(2) . . ? C13 B1 C1 115.71(18) . . ? C13 B1 C7 113.25(18) . . ? C1 B1 C7 111.23(18) . . ? O1 B2 O2 115.7(2) . . ? O1 B2 C21 122.7(2) . . ? O2 B2 C21 121.6(2) . . ? C2 C1 C6 113.3(2) . . ? C2 C1 B1 127.7(2) . . ? C6 C1 B1 118.9(2) . . ? F1 C2 C3 115.4(2) . . ? F1 C2 C1 120.3(2) . . ? C3 C2 C1 124.3(2) . . ? F2 C3 C4 119.6(2) . . ? F2 C3 C2 120.9(2) . . ? C4 C3 C2 119.5(2) . . ? F3 C4 C3 120.4(2) . . ? F3 C4 C5 120.4(2) . . ? C3 C4 C5 119.2(2) . . ? F4 C5 C4 120.2(2) . . ? F4 C5 C6 121.0(2) . . ? C4 C5 C6 118.8(2) . . ? F5 C6 C5 115.6(2) . . ? F5 C6 C1 119.5(2) . . ? C5 C6 C1 124.9(2) . . ? C8 C7 C12 113.6(2) . . ? C8 C7 B1 125.4(2) . . ? C12 C7 B1 120.9(2) . . ? F6 C8 C7 119.6(2) . . ? F6 C8 C9 116.4(2) . . ? C7 C8 C9 124.0(2) . . ? F7 C9 C10 119.7(2) . . ? F7 C9 C8 121.2(2) . . ? C10 C9 C8 119.1(2) . . ? F8 C10 C11 120.0(3) . . ? F8 C10 C9 120.8(3) . . ? C11 C10 C9 119.2(2) . . ? F9 C11 C12 120.7(2) . . ? F9 C11 C10 119.7(2) . . ? C12 C11 C10 119.5(2) . . ? F10 C12 C11 115.8(2) . . ? F10 C12 C7 119.7(2) . . ? C11 C12 C7 124.5(2) . . ? C14 C13 C18 113.1(2) . . ? C14 C13 B1 121.48(19) . . ? C18 C13 B1 125.3(2) . . ? F11 C14 C15 115.8(2) . . ? F11 C14 C13 119.4(2) . . ? C15 C14 C13 124.8(2) . . ? F12 C15 C14 120.9(2) . . ? F12 C15 C16 119.7(2) . . ? C14 C15 C16 119.4(2) . . ? F13 C16 C17 120.8(2) . . ? F13 C16 C15 120.4(2) . . ? C17 C16 C15 118.7(2) . . ? F14 C17 C16 119.7(2) . . ? F14 C17 C18 120.6(2) . . ? C16 C17 C18 119.7(2) . . ? F15 C18 C17 116.1(2) . . ? F15 C18 C13 119.75(19) . . ? C17 C18 C13 124.1(2) . . ? N1 C19 C20 117.3(2) . . ? N1 C19 C24 117.7(2) . . ? C20 C19 C24 125.0(2) . . ? C19 C20 C21 120.8(2) . . ? C20 C21 C22 118.7(2) . . ? C20 C21 B2 121.0(2) . . ? C22 C21 B2 120.4(2) . . ? C23 C22 C21 120.8(2) . . ? N1 C23 C22 117.2(2) . . ? N1 C23 C25 117.6(2) . . ? C22 C23 C25 125.1(2) . . ? O1 C26 C27 109.0(2) . . ? O1 C26 C28 105.6(2) . . ? C27 C26 C28 110.4(3) . . ? O1 C26 C29 102.31(19) . . ? C27 C26 C29 115.7(3) . . ? C28 C26 C29 113.0(3) . . ? O2 C29 C31 108.3(2) . . ? O2 C29 C30 106.1(2) . . ? C31 C29 C30 110.2(3) . . ? O2 C29 C26 102.4(2) . . ? C31 C29 C26 115.4(2) . . ? C30 C29 C26 113.6(3) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.378 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.050 # Attachment '- 2-CBC007_0m.cif' data_cbc007_0m _database_code_depnum_ccdc_archive 'CCDC 846345' #TrackingRef '- 2-CBC007_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H18 B F15 N2' _chemical_formula_weight 726.29 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.2901(7) _cell_length_b 16.2725(11) _cell_length_c 17.1597(12) _cell_angle_alpha 81.189(3) _cell_angle_beta 74.757(3) _cell_angle_gamma 88.279(4) _cell_volume 3005.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 16294 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 28.09 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 0.159 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6457 _exptl_absorpt_correction_T_max 0.7459 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 57933 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0447 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.24 _diffrn_reflns_theta_max 29.36 _reflns_number_total 16294 _reflns_number_gt 9681 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0881P)^2^+1.2912P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 16294 _refine_ls_number_parameters 917 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1117 _refine_ls_R_factor_gt 0.0632 _refine_ls_wR_factor_ref 0.1940 _refine_ls_wR_factor_gt 0.1657 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 C7 C 0.07158(19) 0.24146(12) 0.26120(12) 0.0287(4) Uani 1 1 d . . . C2 C 0.1798(2) 0.10529(14) 0.38228(13) 0.0328(5) Uani 1 1 d . . . C8 C 0.00156(19) 0.18451(13) 0.24000(13) 0.0319(4) Uani 1 1 d . . . C13 C 0.28821(18) 0.20676(13) 0.16355(13) 0.0311(4) Uani 1 1 d . . . C10 C -0.1780(2) 0.26692(16) 0.26101(15) 0.0427(6) Uani 1 1 d . . . C6 C 0.3776(2) 0.15758(15) 0.32609(14) 0.0393(5) Uani 1 1 d . . . C1 C 0.25546(19) 0.16284(13) 0.32433(13) 0.0303(4) Uani 1 1 d . . . C11 C -0.1141(2) 0.32552(14) 0.28317(14) 0.0398(5) Uani 1 1 d . . . C12 C 0.0076(2) 0.31202(13) 0.28316(13) 0.0318(5) Uani 1 1 d . . . C3 C 0.2210(2) 0.04702(15) 0.43641(14) 0.0411(5) Uani 1 1 d . . . C14 C 0.3214(2) 0.12780(14) 0.14539(14) 0.0355(5) Uani 1 1 d . . . C9 C -0.1204(2) 0.19503(15) 0.24001(15) 0.0393(5) Uani 1 1 d . . . C18 C 0.3228(2) 0.26775(16) 0.09632(16) 0.0459(6) Uani 1 1 d . . . C15 C 0.3844(2) 0.11102(19) 0.06893(16) 0.0506(7) Uani 1 1 d . . . C16 C 0.4162(3) 0.1750(3) 0.00549(16) 0.0649(9) Uani 1 1 d . . . C5 C 0.4224(2) 0.09974(19) 0.37862(16) 0.0507(7) Uani 1 1 d . . . C4 C 0.3431(3) 0.04408(18) 0.43396(16) 0.0514(7) Uani 1 1 d . . . C17 C 0.3859(3) 0.2541(2) 0.01895(16) 0.0613(8) Uani 1 1 d . . . C31 C 0.60990(19) 0.74464(12) 0.26627(12) 0.0300(4) Uani 1 1 d . . . C36 C 0.5349(2) 0.69779(13) 0.23763(13) 0.0335(5) Uani 1 1 d . . . C25 C 0.81997(19) 0.70999(14) 0.16411(14) 0.0353(5) Uani 1 1 d . . . C32 C 0.5546(2) 0.81530(13) 0.29435(14) 0.0349(5) Uani 1 1 d . . . C19 C 0.7885(2) 0.64858(14) 0.32263(14) 0.0378(5) Uani 1 1 d . . . C33 C 0.4379(2) 0.84003(14) 0.29102(16) 0.0440(6) Uani 1 1 d . . . C35 C 0.4168(2) 0.71884(16) 0.23442(15) 0.0423(6) Uani 1 1 d . . . C24 C 0.7092(2) 0.59029(15) 0.37667(15) 0.0426(6) Uani 1 1 d . . . C20 C 0.9102(2) 0.63676(18) 0.32294(16) 0.0488(6) Uani 1 1 d . . . C34 C 0.3686(2) 0.79143(17) 0.26074(16) 0.0481(6) Uani 1 1 d . . . C26 C 0.8437(2) 0.63339(16) 0.13763(15) 0.0454(6) Uani 1 1 d . . . C22 C 0.8688(3) 0.5151(2) 0.42147(18) 0.0643(9) Uani 1 1 d . . . C23 C 0.7457(3) 0.52387(17) 0.42609(16) 0.0552(7) Uani 1 1 d . . . C30 C 0.8554(2) 0.77613(18) 0.10183(17) 0.0517(7) Uani 1 1 d . . . C21 C 0.9517(3) 0.5711(2) 0.37084(18) 0.0647(9) Uani 1 1 d . . . C29 C 0.9122(3) 0.7694(3) 0.02196(19) 0.0731(10) Uani 1 1 d . . . C27 C 0.8998(3) 0.6233(2) 0.05794(18) 0.0705(10) Uani 1 1 d . . . C28 C 0.9352(3) 0.6923(3) -0.00012(18) 0.0817(12) Uani 1 1 d . . . C55 C 0.83769(19) 0.76007(13) 0.47945(13) 0.0318(4) Uani 1 1 d . . . C59 C 0.9021(2) 0.88213(14) 0.38251(14) 0.0376(5) Uani 1 1 d . . . C60 C 0.73001(19) 0.70686(13) 0.52354(13) 0.0307(4) Uani 1 1 d . . . C63 C 0.5240(2) 0.61908(16) 0.60102(15) 0.0426(6) Uani 1 1 d . . . H63A H 0.4495 0.5898 0.6282 0.051 Uiso 1 1 calc R . . C61 C 0.7386(2) 0.63579(14) 0.57636(13) 0.0337(5) Uani 1 1 d . . . H61A H 0.8157 0.6186 0.5854 0.040 Uiso 1 1 calc R . . C62 C 0.6331(2) 0.58960(15) 0.61629(13) 0.0376(5) Uani 1 1 d . . . C56 C 0.9530(2) 0.75123(14) 0.49114(14) 0.0375(5) Uani 1 1 d . . . H56A H 0.9699 0.7057 0.5283 0.045 Uiso 1 1 calc R . . C64 C 0.5225(2) 0.69146(15) 0.54598(15) 0.0409(5) Uani 1 1 d . . . C57 C 1.0452(2) 0.80809(16) 0.44926(16) 0.0451(6) Uani 1 1 d . . . C54 C 0.6392(2) 0.50949(17) 0.67200(17) 0.0535(7) Uani 1 1 d . . . H54A H 0.7241 0.4996 0.6747 0.080 Uiso 1 1 calc R . . H54B H 0.6104 0.4635 0.6507 0.080 Uiso 1 1 calc R . . H54C H 0.5869 0.5133 0.7268 0.080 Uiso 1 1 calc R . . C58 C 1.0183(2) 0.87336(16) 0.39419(16) 0.0438(6) Uani 1 1 d . . . H58A H 1.0809 0.9124 0.3643 0.053 Uiso 1 1 calc R . . C52 C 0.8646(3) 0.95159(16) 0.32658(17) 0.0508(6) Uani 1 1 d . . . H52A H 0.7779 0.9446 0.3286 0.076 Uiso 1 1 calc R . . H52B H 0.9149 0.9510 0.2706 0.076 Uiso 1 1 calc R . . H52C H 0.8765 1.0048 0.3438 0.076 Uiso 1 1 calc R . . C53 C 0.4068(2) 0.72413(19) 0.5258(2) 0.0591(8) Uani 1 1 d . . . H53A H 0.4253 0.7753 0.4863 0.089 Uiso 1 1 calc R . . H53B H 0.3475 0.7360 0.5757 0.089 Uiso 1 1 calc R . . H53C H 0.3720 0.6824 0.5023 0.089 Uiso 1 1 calc R . . C51 C 1.1698(2) 0.7985(2) 0.4657(2) 0.0683(9) Uani 1 1 d . . . H51A H 1.2245 0.8432 0.4316 0.102 Uiso 1 1 calc R . . H51B H 1.2039 0.7446 0.4528 0.102 Uiso 1 1 calc R . . H51C H 1.1622 0.8013 0.5235 0.102 Uiso 1 1 calc R . . C42 C 0.3172(3) 0.84742(17) -0.07998(18) 0.0504(7) Uani 1 1 d . . . H42A H 0.3666 0.8241 -0.1250 0.060 Uiso 1 1 calc R . . C41 C 0.2633(3) 0.79827(16) -0.0127(2) 0.0547(8) Uani 1 1 d . . . C44 C 0.2295(3) 0.96243(15) -0.01994(19) 0.0536(7) Uani 1 1 d . . . H44A H 0.2161 1.0206 -0.0227 0.064 Uiso 1 1 calc R . . C46 C 0.2784(3) 0.70694(16) -0.0071(2) 0.0579(8) Uani 1 1 d . . . C49 C 0.2994(3) 0.53925(16) 0.00961(18) 0.0584(8) Uani 1 1 d . . . H49A H 0.3079 0.4806 0.0147 0.070 Uiso 1 1 calc R . . C45 C 0.1743(3) 0.90939(18) 0.05125(19) 0.0553(7) Uani 1 1 d . . . C43 C 0.3032(3) 0.93169(19) -0.08634(19) 0.0559(7) Uani 1 1 d . . . C50 C 0.2252(3) 0.57450(18) 0.07343(17) 0.0590(8) Uani 1 1 d . . . C47 C 0.3469(3) 0.67246(15) -0.06703(18) 0.0521(7) Uani 1 1 d . . . H47A H 0.3880 0.7069 -0.1160 0.063 Uiso 1 1 calc R . . C48 C 0.3611(3) 0.58853(18) -0.06150(18) 0.0595(7) Uani 1 1 d . . . C38 C 0.1555(4) 0.5265(3) 0.1514(2) 0.1093(17) Uani 1 1 d . . . H38A H 0.1690 0.4669 0.1497 0.164 Uiso 1 1 calc R . . H38B H 0.0678 0.5383 0.1597 0.164 Uiso 1 1 calc R . . H38C H 0.1836 0.5423 0.1965 0.164 Uiso 1 1 calc R . . C39 C 0.0972(4) 0.9400(3) 0.1263(3) 0.1002(14) Uani 1 1 d . . . H39A H 0.0676 0.8925 0.1691 0.150 Uiso 1 1 calc R . . H39B H 0.0270 0.9706 0.1133 0.150 Uiso 1 1 calc R . . H39C H 0.1467 0.9769 0.1456 0.150 Uiso 1 1 calc R . . C40 C 0.3670(4) 0.9874(3) -0.1642(2) 0.1106(17) Uani 1 1 d . . . H40A H 0.4145 0.9533 -0.2036 0.166 Uiso 1 1 calc R . . H40B H 0.4222 1.0261 -0.1521 0.166 Uiso 1 1 calc R . . H40C H 0.3055 1.0188 -0.1872 0.166 Uiso 1 1 calc R . . C37 C 0.4393(4) 0.5510(3) -0.1326(2) 0.1037(15) Uani 1 1 d . . . H37A H 0.4754 0.5954 -0.1773 0.156 Uiso 1 1 calc R . . H37B H 0.3884 0.5146 -0.1514 0.156 Uiso 1 1 calc R . . H37C H 0.5050 0.5184 -0.1154 0.156 Uiso 1 1 calc R . . F10 F 0.06299(13) 0.37275(8) 0.30698(8) 0.0431(3) Uani 1 1 d . . . F6 F 0.05298(12) 0.11272(8) 0.21783(9) 0.0427(3) Uani 1 1 d . . . F1 F 0.05857(12) 0.10161(9) 0.38770(8) 0.0439(3) Uani 1 1 d . . . F5 F 0.46111(13) 0.21020(10) 0.27187(9) 0.0540(4) Uani 1 1 d . . . F11 F 0.29407(14) 0.06047(8) 0.20423(8) 0.0460(3) Uani 1 1 d . . . F7 F -0.18145(14) 0.13655(10) 0.21794(10) 0.0589(4) Uani 1 1 d . . . F2 F 0.14218(15) -0.00820(10) 0.49092(9) 0.0567(4) Uani 1 1 d . . . F9 F -0.17047(14) 0.39590(9) 0.30443(10) 0.0591(4) Uani 1 1 d . . . F8 F -0.29608(13) 0.27944(11) 0.25970(11) 0.0637(5) Uani 1 1 d . . . F4 F 0.54322(15) 0.09839(14) 0.37513(12) 0.0816(6) Uani 1 1 d . . . F15 F 0.29546(17) 0.34830(10) 0.10482(11) 0.0693(5) Uani 1 1 d . . . F3 F 0.38294(17) -0.01361(13) 0.48599(11) 0.0848(6) Uani 1 1 d . . . F12 F 0.41383(17) 0.03234(12) 0.05768(11) 0.0753(6) Uani 1 1 d . . . F14 F 0.4178(2) 0.31791(16) -0.04253(12) 0.1029(8) Uani 1 1 d . . . F13 F 0.4788(2) 0.15902(18) -0.06899(11) 0.1054(8) Uani 1 1 d . . . F30 F 0.57745(13) 0.62633(8) 0.21025(8) 0.0436(3) Uani 1 1 d . . . F26 F 0.61586(13) 0.86672(8) 0.32606(9) 0.0454(3) Uani 1 1 d . . . F20 F 0.58721(14) 0.59407(9) 0.38346(9) 0.0516(4) Uani 1 1 d . . . F21 F 0.81316(17) 0.56240(9) 0.19060(9) 0.0619(5) Uani 1 1 d . . . F16 F 0.99745(14) 0.68980(13) 0.27288(10) 0.0671(5) Uani 1 1 d . . . F29 F 0.35014(14) 0.67060(11) 0.20434(10) 0.0606(4) Uani 1 1 d . . . F27 F 0.39152(14) 0.91115(9) 0.31746(11) 0.0666(5) Uani 1 1 d . . . F25 F 0.83468(19) 0.85477(10) 0.11904(13) 0.0794(6) Uani 1 1 d . . . F19 F 0.6640(2) 0.46935(10) 0.47673(11) 0.0770(6) Uani 1 1 d . . . F28 F 0.25470(14) 0.81438(12) 0.25654(12) 0.0746(5) Uani 1 1 d . . . F17 F 1.07184(18) 0.56237(16) 0.36545(12) 0.0991(8) Uani 1 1 d . . . F18 F 0.9065(2) 0.44912(13) 0.46723(11) 0.0969(8) Uani 1 1 d . . . F24 F 0.9459(2) 0.83738(18) -0.03472(14) 0.1186(10) Uani 1 1 d . . . F22 F 0.9184(3) 0.54654(16) 0.03790(13) 0.1180(10) Uani 1 1 d . . . F23 F 0.9913(2) 0.6823(2) -0.07769(11) 0.1394(12) Uani 1 1 d . . . B1 B 0.2186(2) 0.23046(14) 0.25385(15) 0.0300(5) Uani 1 1 d . . . B2 B 0.7554(2) 0.72501(15) 0.25831(16) 0.0328(5) Uani 1 1 d . . . N4 N 0.81685(17) 0.82491(11) 0.42554(11) 0.0342(4) Uani 1 1 d . . . N3 N 0.62437(17) 0.73508(12) 0.50770(12) 0.0360(4) Uani 1 1 d . . . N1 N 0.2198(3) 0.66038(16) 0.06172(18) 0.0668(8) Uani 1 1 d . . . N2 N 0.1923(2) 0.82604(14) 0.05391(17) 0.0607(7) Uani 1 1 d . . . H100 H 0.253(2) 0.2929(15) 0.2589(15) 0.042(7) Uiso 1 1 d . . . H101 H 0.803(2) 0.7856(17) 0.2646(16) 0.056(8) Uiso 1 1 d . . . H4 H 0.729(3) 0.824(2) 0.423(2) 0.088(11) Uiso 1 1 d . . . H1 H 0.159(5) 0.693(3) 0.114(3) 0.17(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C7 0.0321(11) 0.0286(10) 0.0239(10) -0.0017(8) -0.0058(8) 0.0002(8) C2 0.0321(11) 0.0413(11) 0.0263(11) -0.0079(9) -0.0082(9) 0.0018(9) C8 0.0333(11) 0.0296(10) 0.0323(11) -0.0051(8) -0.0071(9) -0.0014(8) C13 0.0254(10) 0.0366(11) 0.0294(11) 0.0002(9) -0.0065(8) -0.0003(8) C10 0.0302(12) 0.0564(15) 0.0422(14) -0.0034(11) -0.0135(10) 0.0046(10) C6 0.0334(12) 0.0529(14) 0.0320(12) -0.0056(10) -0.0096(10) -0.0033(10) C1 0.0311(11) 0.0344(10) 0.0270(11) -0.0101(8) -0.0072(9) 0.0003(8) C11 0.0402(13) 0.0388(12) 0.0373(13) -0.0045(10) -0.0066(10) 0.0126(10) C12 0.0370(12) 0.0306(10) 0.0283(11) -0.0052(8) -0.0089(9) 0.0003(9) C3 0.0454(14) 0.0480(13) 0.0285(12) 0.0007(10) -0.0105(10) -0.0017(11) C14 0.0334(11) 0.0428(12) 0.0306(12) -0.0063(9) -0.0093(9) 0.0073(9) C9 0.0356(12) 0.0450(13) 0.0394(13) -0.0036(10) -0.0143(10) -0.0060(10) C18 0.0410(13) 0.0503(14) 0.0411(14) 0.0097(11) -0.0107(11) -0.0018(11) C15 0.0390(13) 0.0793(19) 0.0395(14) -0.0257(14) -0.0131(11) 0.0183(13) C16 0.0446(16) 0.119(3) 0.0267(14) -0.0107(16) -0.0033(11) 0.0124(17) C5 0.0355(13) 0.0764(18) 0.0445(15) -0.0043(13) -0.0211(12) 0.0032(12) C4 0.0532(16) 0.0666(17) 0.0375(14) 0.0042(12) -0.0250(12) 0.0081(13) C17 0.0501(16) 0.092(2) 0.0308(14) 0.0184(14) -0.0070(12) -0.0061(15) C31 0.0327(11) 0.0298(10) 0.0246(10) -0.0013(8) -0.0039(8) -0.0006(8) C36 0.0347(11) 0.0343(11) 0.0290(11) -0.0029(9) -0.0048(9) -0.0018(9) C25 0.0281(11) 0.0403(12) 0.0359(12) -0.0024(9) -0.0077(9) 0.0041(9) C32 0.0343(11) 0.0313(10) 0.0366(12) -0.0043(9) -0.0053(9) -0.0006(9) C19 0.0434(13) 0.0447(12) 0.0319(12) -0.0183(10) -0.0154(10) 0.0119(10) C33 0.0384(13) 0.0370(12) 0.0483(15) -0.0022(11) -0.0003(11) 0.0085(10) C35 0.0381(13) 0.0550(14) 0.0339(13) 0.0017(11) -0.0129(10) -0.0092(11) C24 0.0565(15) 0.0441(13) 0.0331(13) -0.0098(10) -0.0208(11) 0.0077(11) C20 0.0463(15) 0.0706(17) 0.0351(13) -0.0204(12) -0.0151(12) 0.0187(13) C34 0.0294(12) 0.0591(16) 0.0487(15) 0.0082(12) -0.0075(11) 0.0053(11) C26 0.0508(15) 0.0518(14) 0.0339(13) -0.0092(11) -0.0118(11) 0.0179(11) C22 0.100(3) 0.0671(18) 0.0389(16) -0.0210(14) -0.0375(17) 0.0431(18) C23 0.091(2) 0.0461(14) 0.0378(15) -0.0115(12) -0.0315(15) 0.0129(14) C30 0.0359(13) 0.0596(16) 0.0537(17) 0.0118(13) -0.0128(12) -0.0029(11) C21 0.0625(19) 0.100(2) 0.0444(16) -0.0323(17) -0.0298(15) 0.0450(18) C29 0.0453(17) 0.114(3) 0.0448(18) 0.0277(18) -0.0066(14) -0.0006(18) C27 0.073(2) 0.104(3) 0.0386(16) -0.0283(17) -0.0167(14) 0.0491(19) C28 0.0519(18) 0.153(4) 0.0274(15) -0.0002(19) 0.0007(13) 0.034(2) C55 0.0324(11) 0.0363(11) 0.0278(11) -0.0081(9) -0.0078(9) -0.0001(9) C59 0.0370(12) 0.0417(12) 0.0352(12) -0.0052(10) -0.0113(10) -0.0038(10) C60 0.0293(11) 0.0391(11) 0.0256(11) -0.0077(9) -0.0088(8) -0.0007(8) C63 0.0298(12) 0.0546(14) 0.0403(14) 0.0011(11) -0.0082(10) -0.0036(10) C61 0.0309(11) 0.0443(12) 0.0281(11) -0.0059(9) -0.0116(9) 0.0027(9) C62 0.0367(12) 0.0476(13) 0.0268(11) -0.0002(10) -0.0085(9) 0.0014(10) C56 0.0328(12) 0.0416(12) 0.0387(13) -0.0054(10) -0.0116(10) 0.0051(9) C64 0.0308(12) 0.0507(13) 0.0411(13) -0.0007(11) -0.0128(10) 0.0019(10) C57 0.0271(11) 0.0556(15) 0.0535(16) -0.0080(12) -0.0126(11) 0.0024(10) C54 0.0451(15) 0.0621(16) 0.0457(15) 0.0144(13) -0.0115(12) -0.0007(12) C58 0.0319(12) 0.0488(14) 0.0472(15) -0.0009(11) -0.0068(11) -0.0076(10) C52 0.0530(16) 0.0477(14) 0.0519(16) 0.0072(12) -0.0212(13) -0.0105(12) C53 0.0309(13) 0.0682(18) 0.075(2) 0.0120(15) -0.0212(13) 0.0016(12) C51 0.0321(14) 0.081(2) 0.091(2) 0.0049(18) -0.0251(15) 0.0005(13) C42 0.0546(16) 0.0510(15) 0.0603(18) -0.0232(14) -0.0342(14) 0.0167(12) C41 0.0625(17) 0.0395(13) 0.085(2) -0.0243(14) -0.0514(17) 0.0133(12) C44 0.0599(17) 0.0275(11) 0.080(2) -0.0064(12) -0.0314(16) 0.0018(11) C46 0.084(2) 0.0366(13) 0.074(2) -0.0074(14) -0.0568(18) 0.0064(14) C49 0.085(2) 0.0302(12) 0.0561(18) -0.0051(12) -0.0137(16) 0.0072(13) C45 0.0543(17) 0.0511(15) 0.0647(19) -0.0123(14) -0.0206(14) -0.0028(13) C43 0.0500(16) 0.0652(18) 0.0585(18) -0.0023(14) -0.0283(14) -0.0010(13) C50 0.077(2) 0.0557(16) 0.0459(16) -0.0040(13) -0.0221(15) 0.0199(14) C47 0.0765(19) 0.0337(12) 0.0519(17) 0.0044(12) -0.0316(15) -0.0118(12) C48 0.083(2) 0.0487(15) 0.0476(17) -0.0086(13) -0.0162(15) -0.0066(14) C38 0.093(3) 0.153(4) 0.053(2) 0.029(2) 0.002(2) 0.039(3) C39 0.077(3) 0.142(4) 0.082(3) -0.048(3) -0.005(2) 0.000(2) C40 0.076(3) 0.176(5) 0.069(3) 0.033(3) -0.026(2) -0.030(3) C37 0.116(3) 0.123(4) 0.063(2) -0.037(2) 0.009(2) -0.022(3) F10 0.0498(8) 0.0361(7) 0.0472(8) -0.0183(6) -0.0131(6) 0.0044(6) F6 0.0407(7) 0.0318(6) 0.0561(9) -0.0149(6) -0.0086(6) -0.0019(5) F1 0.0317(7) 0.0558(8) 0.0388(8) 0.0064(6) -0.0071(6) -0.0048(6) F5 0.0338(7) 0.0741(10) 0.0518(9) 0.0061(8) -0.0142(7) -0.0148(7) F11 0.0646(9) 0.0317(6) 0.0422(8) -0.0082(6) -0.0142(7) 0.0099(6) F7 0.0480(9) 0.0626(10) 0.0756(11) -0.0162(8) -0.0284(8) -0.0117(7) F2 0.0607(10) 0.0625(9) 0.0401(8) 0.0172(7) -0.0141(7) -0.0094(8) F9 0.0518(9) 0.0515(9) 0.0742(11) -0.0203(8) -0.0136(8) 0.0239(7) F8 0.0346(8) 0.0814(11) 0.0791(12) -0.0104(9) -0.0239(8) 0.0115(7) F4 0.0393(9) 0.1284(17) 0.0745(12) 0.0214(11) -0.0303(9) -0.0030(9) F15 0.0859(13) 0.0421(8) 0.0692(12) 0.0215(8) -0.0177(9) -0.0052(8) F3 0.0705(12) 0.1117(15) 0.0688(12) 0.0341(11) -0.0397(10) 0.0059(11) F12 0.0761(12) 0.0955(13) 0.0666(11) -0.0523(10) -0.0221(9) 0.0421(10) F14 0.1056(17) 0.1304(19) 0.0456(11) 0.0425(12) -0.0023(11) -0.0162(14) F13 0.0899(15) 0.183(3) 0.0314(10) -0.0241(12) 0.0068(9) 0.0267(15) F30 0.0482(8) 0.0391(7) 0.0435(8) -0.0140(6) -0.0071(6) -0.0061(6) F26 0.0488(8) 0.0359(7) 0.0521(9) -0.0171(6) -0.0082(7) 0.0010(6) F20 0.0551(9) 0.0546(9) 0.0451(9) 0.0056(7) -0.0194(7) -0.0091(7) F21 0.1049(13) 0.0373(7) 0.0468(9) -0.0133(7) -0.0231(9) 0.0172(8) F16 0.0380(9) 0.1105(14) 0.0554(10) -0.0163(10) -0.0155(8) 0.0110(9) F29 0.0491(9) 0.0789(11) 0.0595(10) -0.0040(8) -0.0257(8) -0.0170(8) F27 0.0529(9) 0.0464(8) 0.0894(13) -0.0127(8) 0.0001(9) 0.0204(7) F25 0.0960(14) 0.0428(9) 0.0969(15) 0.0197(9) -0.0365(12) -0.0124(9) F19 0.1350(17) 0.0513(9) 0.0509(10) 0.0088(8) -0.0434(11) -0.0070(10) F28 0.0375(9) 0.0904(13) 0.0925(14) 0.0026(10) -0.0223(9) 0.0151(8) F17 0.0688(12) 0.172(2) 0.0661(12) -0.0290(13) -0.0361(10) 0.0658(14) F18 0.155(2) 0.0930(14) 0.0597(12) -0.0176(10) -0.0615(13) 0.0699(14) F24 0.0978(17) 0.158(2) 0.0699(14) 0.0675(15) -0.0137(12) -0.0315(15) F22 0.168(2) 0.133(2) 0.0699(13) -0.0658(14) -0.0424(14) 0.0945(18) F23 0.1083(19) 0.257(4) 0.0316(10) -0.0103(15) 0.0045(11) 0.070(2) B1 0.0280(12) 0.0257(10) 0.0350(13) -0.0026(9) -0.0067(10) -0.0021(9) B2 0.0309(12) 0.0313(12) 0.0371(14) -0.0092(10) -0.0082(10) 0.0009(9) N4 0.0295(10) 0.0396(10) 0.0349(10) -0.0059(8) -0.0105(8) -0.0022(8) N3 0.0304(10) 0.0416(10) 0.0376(11) -0.0046(8) -0.0122(8) 0.0004(8) N1 0.0867(19) 0.0586(15) 0.0769(19) -0.0312(14) -0.0508(16) 0.0320(14) N2 0.0710(16) 0.0457(13) 0.0741(18) -0.0010(12) -0.0371(14) -0.0110(12) _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 C7 C8 1.384(3) . ? C7 C12 1.386(3) . ? C7 B1 1.638(3) . ? C2 F1 1.350(2) . ? C2 C3 1.382(3) . ? C2 C1 1.382(3) . ? C8 F6 1.351(2) . ? C8 C9 1.383(3) . ? C13 C18 1.380(3) . ? C13 C14 1.386(3) . ? C13 B1 1.641(3) . ? C10 F8 1.348(3) . ? C10 C11 1.368(4) . ? C10 C9 1.371(3) . ? C6 F5 1.353(3) . ? C6 C5 1.381(3) . ? C6 C1 1.387(3) . ? C1 B1 1.636(3) . ? C11 F9 1.346(3) . ? C11 C12 1.385(3) . ? C12 F10 1.353(2) . ? C3 F2 1.352(3) . ? C3 C4 1.367(4) . ? C14 F11 1.354(3) . ? C14 C15 1.382(3) . ? C9 F7 1.346(3) . ? C18 F15 1.358(3) . ? C18 C17 1.380(4) . ? C15 F12 1.343(3) . ? C15 C16 1.366(4) . ? C16 F13 1.347(3) . ? C16 C17 1.361(5) . ? C5 F4 1.349(3) . ? C5 C4 1.365(4) . ? C4 F3 1.345(3) . ? C17 F14 1.344(3) . ? C31 C32 1.383(3) . ? C31 C36 1.383(3) . ? C31 B2 1.638(3) . ? C36 F30 1.349(2) . ? C36 C35 1.380(3) . ? C25 C30 1.382(3) . ? C25 C26 1.386(3) . ? C25 B2 1.642(3) . ? C32 F26 1.359(3) . ? C32 C33 1.380(3) . ? C19 C24 1.381(4) . ? C19 C20 1.383(3) . ? C19 B2 1.635(3) . ? C33 F27 1.348(3) . ? C33 C34 1.373(4) . ? C35 F29 1.346(3) . ? C35 C34 1.375(4) . ? C24 F20 1.351(3) . ? C24 C23 1.390(3) . ? C20 F16 1.353(3) . ? C20 C21 1.392(4) . ? C34 F28 1.345(3) . ? C26 F21 1.348(3) . ? C26 C27 1.380(4) . ? C22 F18 1.357(3) . ? C22 C21 1.358(5) . ? C22 C23 1.375(5) . ? C23 F19 1.336(4) . ? C30 F25 1.357(3) . ? C30 C29 1.372(4) . ? C21 F17 1.340(3) . ? C29 F24 1.348(4) . ? C29 C28 1.363(6) . ? C27 F22 1.341(4) . ? C27 C28 1.375(5) . ? C28 F23 1.348(4) . ? C55 N4 1.351(3) . ? C55 C56 1.369(3) . ? C55 C60 1.476(3) . ? C59 N4 1.345(3) . ? C59 C58 1.378(3) . ? C59 C52 1.493(3) . ? C60 N3 1.344(3) . ? C60 C61 1.374(3) . ? C63 C62 1.383(3) . ? C63 C64 1.395(3) . ? C61 C62 1.385(3) . ? C62 C54 1.505(3) . ? C56 C57 1.384(3) . ? C64 N3 1.329(3) . ? C64 C53 1.499(3) . ? C57 C58 1.392(3) . ? C57 C51 1.506(3) . ? C42 C41 1.312(4) . ? C42 C43 1.366(4) . ? C41 N2 1.344(4) . ? C41 C46 1.482(4) . ? C44 C43 1.376(4) . ? C44 C45 1.391(4) . ? C46 C47 1.304(4) . ? C46 N1 1.324(4) . ? C49 C48 1.380(4) . ? C49 C50 1.383(4) . ? C45 N2 1.361(4) . ? C45 C39 1.498(5) . ? C43 C40 1.512(5) . ? C50 N1 1.383(4) . ? C50 C38 1.477(5) . ? C47 C48 1.362(4) . ? C48 C37 1.507(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 C8 C7 C12 113.47(19) . . ? C8 C7 B1 123.39(18) . . ? C12 C7 B1 122.95(18) . . ? F1 C2 C3 115.4(2) . . ? F1 C2 C1 120.82(19) . . ? C3 C2 C1 123.8(2) . . ? F6 C8 C9 116.05(19) . . ? F6 C8 C7 119.34(18) . . ? C9 C8 C7 124.6(2) . . ? C18 C13 C14 112.7(2) . . ? C18 C13 B1 121.0(2) . . ? C14 C13 B1 126.25(18) . . ? F8 C10 C11 120.6(2) . . ? F8 C10 C9 120.2(2) . . ? C11 C10 C9 119.2(2) . . ? F5 C6 C5 116.3(2) . . ? F5 C6 C1 119.3(2) . . ? C5 C6 C1 124.3(2) . . ? C2 C1 C6 113.6(2) . . ? C2 C1 B1 127.96(19) . . ? C6 C1 B1 118.38(19) . . ? F9 C11 C10 119.4(2) . . ? F9 C11 C12 120.8(2) . . ? C10 C11 C12 119.8(2) . . ? F10 C12 C11 115.70(18) . . ? F10 C12 C7 120.45(19) . . ? C11 C12 C7 123.8(2) . . ? F2 C3 C4 119.5(2) . . ? F2 C3 C2 120.7(2) . . ? C4 C3 C2 119.8(2) . . ? F11 C14 C15 115.1(2) . . ? F11 C14 C13 120.61(19) . . ? C15 C14 C13 124.3(2) . . ? F7 C9 C10 120.2(2) . . ? F7 C9 C8 120.7(2) . . ? C10 C9 C8 119.1(2) . . ? F15 C18 C17 115.6(2) . . ? F15 C18 C13 119.3(2) . . ? C17 C18 C13 125.0(3) . . ? F12 C15 C16 120.7(2) . . ? F12 C15 C14 119.9(3) . . ? C16 C15 C14 119.4(3) . . ? F13 C16 C17 121.0(3) . . ? F13 C16 C15 119.7(3) . . ? C17 C16 C15 119.3(2) . . ? F4 C5 C4 120.6(2) . . ? F4 C5 C6 120.3(2) . . ? C4 C5 C6 119.2(2) . . ? F3 C4 C5 121.1(2) . . ? F3 C4 C3 119.5(2) . . ? C5 C4 C3 119.4(2) . . ? F14 C17 C16 120.1(3) . . ? F14 C17 C18 120.8(3) . . ? C16 C17 C18 119.1(3) . . ? C32 C31 C36 113.73(19) . . ? C32 C31 B2 122.37(19) . . ? C36 C31 B2 123.54(18) . . ? F30 C36 C35 116.1(2) . . ? F30 C36 C31 119.36(19) . . ? C35 C36 C31 124.5(2) . . ? C30 C25 C26 113.0(2) . . ? C30 C25 B2 121.2(2) . . ? C26 C25 B2 125.8(2) . . ? F26 C32 C33 115.37(19) . . ? F26 C32 C31 120.62(19) . . ? C33 C32 C31 124.0(2) . . ? C24 C19 C20 113.8(2) . . ? C24 C19 B2 127.8(2) . . ? C20 C19 B2 118.3(2) . . ? F27 C33 C34 120.0(2) . . ? F27 C33 C32 120.6(2) . . ? C34 C33 C32 119.4(2) . . ? F29 C35 C34 120.1(2) . . ? F29 C35 C36 121.0(2) . . ? C34 C35 C36 118.9(2) . . ? F20 C24 C19 120.6(2) . . ? F20 C24 C23 115.1(2) . . ? C19 C24 C23 124.4(3) . . ? F16 C20 C19 119.8(2) . . ? F16 C20 C21 116.1(3) . . ? C19 C20 C21 124.1(3) . . ? F28 C34 C33 120.6(2) . . ? F28 C34 C35 120.1(2) . . ? C33 C34 C35 119.4(2) . . ? F21 C26 C27 115.4(2) . . ? F21 C26 C25 120.6(2) . . ? C27 C26 C25 124.1(3) . . ? F18 C22 C21 120.4(3) . . ? F18 C22 C23 119.2(3) . . ? C21 C22 C23 120.4(3) . . ? F19 C23 C22 120.3(3) . . ? F19 C23 C24 121.3(3) . . ? C22 C23 C24 118.4(3) . . ? F25 C30 C29 115.8(3) . . ? F25 C30 C25 119.1(3) . . ? C29 C30 C25 125.1(3) . . ? F17 C21 C22 120.6(3) . . ? F17 C21 C20 120.4(3) . . ? C22 C21 C20 118.9(3) . . ? F24 C29 C28 119.6(3) . . ? F24 C29 C30 121.2(4) . . ? C28 C29 C30 119.1(3) . . ? F22 C27 C28 120.8(3) . . ? F22 C27 C26 119.9(3) . . ? C28 C27 C26 119.3(3) . . ? F23 C28 C29 121.5(4) . . ? F23 C28 C27 119.2(4) . . ? C29 C28 C27 119.3(3) . . ? N4 C55 C56 118.3(2) . . ? N4 C55 C60 115.73(18) . . ? C56 C55 C60 125.9(2) . . ? N4 C59 C58 117.5(2) . . ? N4 C59 C52 118.2(2) . . ? C58 C59 C52 124.3(2) . . ? N3 C60 C61 123.9(2) . . ? N3 C60 C55 113.77(18) . . ? C61 C60 C55 122.33(19) . . ? C62 C63 C64 120.5(2) . . ? C60 C61 C62 119.0(2) . . ? C63 C62 C61 117.3(2) . . ? C63 C62 C54 122.0(2) . . ? C61 C62 C54 120.7(2) . . ? C55 C56 C57 120.5(2) . . ? N3 C64 C63 121.6(2) . . ? N3 C64 C53 116.1(2) . . ? C63 C64 C53 122.2(2) . . ? C56 C57 C58 118.5(2) . . ? C56 C57 C51 119.3(2) . . ? C58 C57 C51 122.2(2) . . ? C59 C58 C57 120.9(2) . . ? C41 C42 C43 121.0(3) . . ? C42 C41 N2 123.4(2) . . ? C42 C41 C46 120.3(3) . . ? N2 C41 C46 116.3(3) . . ? C43 C44 C45 120.8(2) . . ? C47 C46 N1 120.3(3) . . ? C47 C46 C41 122.2(3) . . ? N1 C46 C41 117.5(3) . . ? C48 C49 C50 120.6(3) . . ? N2 C45 C44 119.0(3) . . ? N2 C45 C39 118.1(3) . . ? C44 C45 C39 122.9(3) . . ? C42 C43 C44 117.3(3) . . ? C42 C43 C40 120.2(3) . . ? C44 C43 C40 122.4(3) . . ? C49 C50 N1 116.0(3) . . ? C49 C50 C38 124.2(3) . . ? N1 C50 C38 119.8(3) . . ? C46 C47 C48 122.0(3) . . ? C47 C48 C49 118.3(3) . . ? C47 C48 C37 120.4(3) . . ? C49 C48 C37 121.3(3) . . ? C1 B1 C7 116.13(17) . . ? C1 B1 C13 109.23(16) . . ? C7 B1 C13 109.39(17) . . ? C19 B2 C31 117.37(19) . . ? C19 B2 C25 110.01(17) . . ? C31 B2 C25 108.13(18) . . ? C59 N4 C55 124.27(19) . . ? C64 N3 C60 117.64(19) . . ? C46 N1 C50 122.7(3) . . ? C41 N2 C45 118.4(3) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 29.36 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.516 _refine_diff_density_min -0.475 _refine_diff_density_rms 0.058 # Attachment '- 4-cbc013_0m.cif' data_cbc013_0m _database_code_depnum_ccdc_archive 'CCDC 846346' #TrackingRef '- 4-cbc013_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H16 B F15 N2 O' _chemical_formula_weight 740.28 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2565(9) _cell_length_b 13.5871(14) _cell_length_c 14.3235(15) _cell_angle_alpha 69.707(4) _cell_angle_beta 83.127(5) _cell_angle_gamma 79.205(5) _cell_volume 1656.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7614 _cell_measurement_theta_min 1.8 _cell_measurement_theta_max 28.0 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 0.148 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9667 _exptl_absorpt_correction_T_max 0.9781 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27083 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 27.99 _reflns_number_total 7614 _reflns_number_gt 5736 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.500 0.000 1.000 183.0 33.4 _platon_squeeze_details ; The unit cell contains 1.5 dichloromethane molecules which have been treated as a diffuse contribution to the overall scattering without specific atom positions by SQUEEZE/PLATON. ; _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^)+(0.0683P)^2^+0.1650P] 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 7614 _refine_ls_number_parameters 462 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0559 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1278 _refine_ls_wR_factor_gt 0.1214 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.119 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.91737(10) 0.66367(8) 0.48003(7) 0.0254(2) Uani 1 1 d . . . N1 N 0.96883(12) 0.63807(9) 0.57280(9) 0.0235(3) Uani 1 1 d . . . B1 B 0.79547(17) 0.76249(13) 0.44419(13) 0.0242(3) Uani 1 1 d . . . F1 F 0.97908(10) 0.71199(8) 0.28583(7) 0.0389(2) Uani 1 1 d . . . C1 C 0.86896(15) 0.85038(12) 0.34837(12) 0.0297(3) Uani 1 1 d . . . N2 N 1.25963(16) 0.47206(14) 1.04193(11) 0.0468(4) Uani 1 1 d . . . F2 F 1.09673(12) 0.84282(11) 0.12316(8) 0.0597(3) Uani 1 1 d . . . C2 C 0.95482(16) 0.81615(13) 0.27552(12) 0.0332(4) Uani 1 1 d . . . F3 F 1.05088(14) 1.05567(11) 0.08994(10) 0.0775(4) Uani 1 1 d . . . C3 C 1.01582(18) 0.88246(16) 0.18941(13) 0.0428(4) Uani 1 1 d . . . F4 F 0.88293(13) 1.13291(9) 0.22390(11) 0.0711(4) Uani 1 1 d . . . C4 C 0.99139(19) 0.98946(16) 0.17294(15) 0.0508(5) Uani 1 1 d . . . F5 F 0.75974(11) 1.00596(7) 0.38625(8) 0.0451(3) Uani 1 1 d . . . C5 C 0.90650(19) 1.02791(14) 0.23949(16) 0.0471(5) Uani 1 1 d . . . F6 F 0.53177(10) 0.89905(7) 0.37243(7) 0.0344(2) Uani 1 1 d . . . C6 C 0.84565(17) 0.95945(13) 0.32547(13) 0.0356(4) Uani 1 1 d . . . F7 F 0.33018(10) 0.87118(7) 0.26974(7) 0.0383(2) Uani 1 1 d . . . C7 C 0.67085(14) 0.72941(11) 0.39227(11) 0.0242(3) Uani 1 1 d . . . F8 F 0.35536(10) 0.68799(8) 0.22968(8) 0.0426(3) Uani 1 1 d . . . C8 C 0.54980(15) 0.80611(11) 0.35510(11) 0.0251(3) Uani 1 1 d . . . F9 F 0.58359(11) 0.53007(8) 0.29941(9) 0.0468(3) Uani 1 1 d . . . C9 C 0.44460(15) 0.79397(12) 0.30175(11) 0.0270(3) Uani 1 1 d . . . F10 F 0.78619(10) 0.55486(7) 0.40142(8) 0.0387(2) Uani 1 1 d . . . C10 C 0.45607(16) 0.70098(13) 0.28221(12) 0.0294(3) Uani 1 1 d . . . F11 F 0.93259(10) 0.88488(8) 0.53299(8) 0.0423(3) Uani 1 1 d . . . C11 C 0.57223(17) 0.62188(12) 0.31726(12) 0.0310(3) Uani 1 1 d . . . F12 F 0.82590(14) 0.94995(10) 0.68402(10) 0.0622(4) Uani 1 1 d . . . C12 C 0.67641(15) 0.63711(12) 0.37069(12) 0.0278(3) Uani 1 1 d . . . F13 F 0.56394(14) 0.90075(10) 0.78117(8) 0.0598(3) Uani 1 1 d . . . C13 C 0.72732(15) 0.80177(12) 0.53827(11) 0.0267(3) Uani 1 1 d . . . F14 F 0.41230(12) 0.78391(9) 0.72021(8) 0.0524(3) Uani 1 1 d . . . C14 C 0.80056(17) 0.85891(13) 0.57550(13) 0.0332(4) Uani 1 1 d . . . F15 F 0.50979(9) 0.72190(8) 0.56775(7) 0.0371(2) Uani 1 1 d . . . C15 C 0.7480(2) 0.89391(14) 0.65460(14) 0.0401(4) Uani 1 1 d . . . C16 C 0.6159(2) 0.86973(14) 0.70334(13) 0.0409(4) Uani 1 1 d . . . C17 C 0.53941(18) 0.81127(14) 0.67220(12) 0.0365(4) Uani 1 1 d . . . C18 C 0.59493(16) 0.77951(12) 0.59178(11) 0.0291(3) Uani 1 1 d . . . C19 C 0.90028(15) 0.57066(12) 0.65110(11) 0.0273(3) Uani 1 1 d . . . C20 C 0.95608(16) 0.54148(12) 0.74317(12) 0.0298(3) Uani 1 1 d . . . H20A H 0.9080 0.4959 0.7994 0.036 Uiso 1 1 calc R . . C21 C 1.08124(16) 0.57709(12) 0.75601(11) 0.0277(3) Uani 1 1 d . . . C22 C 1.14855(15) 0.64358(12) 0.67198(11) 0.0264(3) Uani 1 1 d . . . H22A H 1.2335 0.6697 0.6789 0.032 Uiso 1 1 calc R . . C23 C 1.09541(14) 0.67256(11) 0.57891(11) 0.0243(3) Uani 1 1 d . . . C24 C 1.14340(16) 0.54076(13) 0.85516(11) 0.0307(3) Uani 1 1 d . . . C25 C 1.21057(18) 0.60678(14) 0.88445(12) 0.0363(4) Uani 1 1 d . . . H25A H 1.2181 0.6768 0.8408 0.044 Uiso 1 1 calc R . . C26 C 1.26733(19) 0.57046(16) 0.97825(13) 0.0430(4) Uani 1 1 d . . . C27 C 1.1963(2) 0.40740(16) 1.01307(13) 0.0440(4) Uani 1 1 d . . . C28 C 1.13597(18) 0.43898(14) 0.92112(12) 0.0372(4) Uani 1 1 d . . . H28A H 1.0901 0.3914 0.9035 0.045 Uiso 1 1 calc R . . C29 C 1.17443(16) 0.73190(13) 0.48601(11) 0.0318(3) Uani 1 1 d . . . H29A H 1.1092 0.7962 0.4497 0.048 Uiso 1 1 calc R . . H29B H 1.2044 0.6870 0.4441 0.048 Uiso 1 1 calc R . . H29C H 1.2620 0.7518 0.5028 0.048 Uiso 1 1 calc R . . C30 C 0.77625(18) 0.52517(14) 0.63352(13) 0.0379(4) Uani 1 1 d . . . H30A H 0.7107 0.5812 0.5872 0.057 Uiso 1 1 calc R . . H30B H 0.7211 0.4954 0.6969 0.057 Uiso 1 1 calc R . . H30C H 0.8151 0.4690 0.6049 0.057 Uiso 1 1 calc R . . C31 C 1.1928(3) 0.29723(18) 1.08564(16) 0.0643(6) Uani 1 1 d . . . H31A H 1.2386 0.2895 1.1465 0.096 Uiso 1 1 calc R . . H31B H 1.2470 0.2453 1.0557 0.096 Uiso 1 1 calc R . . H31C H 1.0903 0.2850 1.1021 0.096 Uiso 1 1 calc R . . C32 C 1.3399(3) 0.6403(2) 1.01272(17) 0.0677(7) Uani 1 1 d . . . H32A H 1.3739 0.6010 1.0798 0.102 Uiso 1 1 calc R . . H32B H 1.2690 0.7032 1.0142 0.102 Uiso 1 1 calc R . . H32C H 1.4242 0.6624 0.9668 0.102 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 O1 0.0255(5) 0.0255(5) 0.0252(5) -0.0081(4) -0.0085(4) -0.0001(4) N1 0.0230(5) 0.0213(6) 0.0244(6) -0.0054(5) -0.0044(4) -0.0015(5) B1 0.0214(7) 0.0198(8) 0.0304(8) -0.0064(7) -0.0057(6) -0.0023(6) F1 0.0443(5) 0.0373(6) 0.0326(5) -0.0112(4) -0.0017(4) -0.0016(4) C1 0.0234(7) 0.0280(8) 0.0335(8) -0.0026(6) -0.0094(6) -0.0041(6) N2 0.0409(8) 0.0617(11) 0.0298(8) -0.0103(8) -0.0079(6) 0.0052(7) F2 0.0493(6) 0.0778(9) 0.0349(6) -0.0040(6) 0.0060(5) -0.0023(6) C2 0.0264(7) 0.0361(9) 0.0321(8) -0.0038(7) -0.0075(6) -0.0038(6) F3 0.0587(7) 0.0662(8) 0.0675(8) 0.0263(7) 0.0098(6) -0.0157(6) C3 0.0299(8) 0.0537(12) 0.0342(9) -0.0020(8) -0.0053(7) -0.0038(8) F4 0.0555(7) 0.0255(6) 0.1043(10) 0.0120(6) 0.0015(7) -0.0075(5) C4 0.0318(8) 0.0491(12) 0.0477(11) 0.0160(9) -0.0039(8) -0.0095(8) F5 0.0422(5) 0.0235(5) 0.0630(7) -0.0080(5) -0.0033(5) -0.0011(4) C5 0.0340(8) 0.0278(9) 0.0643(12) 0.0068(9) -0.0103(8) -0.0066(7) F6 0.0365(5) 0.0250(5) 0.0438(5) -0.0140(4) -0.0156(4) 0.0035(4) C6 0.0270(7) 0.0278(8) 0.0458(10) -0.0032(7) -0.0071(7) -0.0041(6) F7 0.0319(5) 0.0327(5) 0.0474(6) -0.0092(4) -0.0183(4) 0.0042(4) C7 0.0226(6) 0.0247(8) 0.0244(7) -0.0061(6) -0.0022(5) -0.0046(5) F8 0.0408(5) 0.0412(6) 0.0514(6) -0.0144(5) -0.0215(5) -0.0104(4) C8 0.0272(7) 0.0211(7) 0.0268(7) -0.0078(6) -0.0032(6) -0.0029(5) F9 0.0467(6) 0.0342(6) 0.0722(7) -0.0302(5) -0.0211(5) -0.0015(4) C9 0.0227(6) 0.0267(8) 0.0282(7) -0.0047(6) -0.0055(5) -0.0015(6) F10 0.0349(5) 0.0287(5) 0.0576(6) -0.0215(5) -0.0182(4) 0.0061(4) C10 0.0277(7) 0.0326(8) 0.0301(8) -0.0085(7) -0.0069(6) -0.0102(6) F11 0.0318(5) 0.0394(6) 0.0648(7) -0.0249(5) -0.0103(4) -0.0079(4) C11 0.0324(7) 0.0270(8) 0.0385(9) -0.0152(7) -0.0048(6) -0.0064(6) F12 0.0718(8) 0.0553(7) 0.0819(9) -0.0482(7) -0.0317(7) 0.0023(6) C12 0.0248(7) 0.0238(8) 0.0342(8) -0.0093(6) -0.0051(6) -0.0012(6) F13 0.0859(8) 0.0531(7) 0.0382(6) -0.0258(5) -0.0138(6) 0.0215(6) C13 0.0258(7) 0.0222(7) 0.0321(8) -0.0092(6) -0.0093(6) 0.0010(6) F14 0.0469(6) 0.0605(7) 0.0380(6) -0.0104(5) 0.0098(5) 0.0005(5) C14 0.0290(7) 0.0277(8) 0.0447(9) -0.0141(7) -0.0133(7) 0.0020(6) F15 0.0299(4) 0.0462(6) 0.0377(5) -0.0133(4) -0.0017(4) -0.0137(4) C15 0.0485(10) 0.0296(9) 0.0485(10) -0.0220(8) -0.0228(8) 0.0083(7) C16 0.0547(11) 0.0335(9) 0.0309(9) -0.0150(7) -0.0144(8) 0.0177(8) C17 0.0361(8) 0.0359(9) 0.0292(8) -0.0063(7) -0.0040(6) 0.0075(7) C18 0.0285(7) 0.0283(8) 0.0290(8) -0.0076(6) -0.0087(6) -0.0003(6) C19 0.0265(7) 0.0211(7) 0.0315(8) -0.0052(6) -0.0021(6) -0.0040(6) C20 0.0313(7) 0.0243(8) 0.0296(8) -0.0034(6) 0.0000(6) -0.0060(6) C21 0.0303(7) 0.0226(8) 0.0281(8) -0.0077(6) -0.0038(6) 0.0006(6) C22 0.0248(6) 0.0239(8) 0.0308(8) -0.0090(6) -0.0046(6) -0.0025(6) C23 0.0222(6) 0.0198(7) 0.0288(7) -0.0063(6) -0.0027(5) -0.0012(5) C24 0.0319(7) 0.0305(8) 0.0261(8) -0.0080(7) -0.0027(6) 0.0012(6) C25 0.0398(8) 0.0378(9) 0.0310(8) -0.0116(7) -0.0051(7) -0.0030(7) C26 0.0393(9) 0.0585(12) 0.0316(9) -0.0176(9) -0.0038(7) -0.0026(8) C27 0.0425(9) 0.0444(11) 0.0320(9) -0.0042(8) -0.0042(7) 0.0097(8) C28 0.0413(9) 0.0314(9) 0.0326(9) -0.0051(7) -0.0061(7) 0.0014(7) C29 0.0251(7) 0.0377(9) 0.0291(8) -0.0045(7) -0.0032(6) -0.0078(6) C30 0.0368(8) 0.0311(9) 0.0425(10) -0.0018(7) -0.0076(7) -0.0142(7) C31 0.0741(14) 0.0501(13) 0.0408(11) 0.0087(10) -0.0088(10) 0.0146(11) C32 0.0734(15) 0.0948(19) 0.0489(12) -0.0329(13) -0.0134(11) -0.0234(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 O1 N1 1.3720(15) . ? O1 B1 1.5596(18) . ? N1 C19 1.3544(18) . ? N1 C23 1.3634(18) . ? B1 C13 1.633(2) . ? B1 C1 1.648(2) . ? B1 C7 1.648(2) . ? F1 C2 1.349(2) . ? C1 C6 1.382(2) . ? C1 C2 1.392(2) . ? N2 C27 1.338(3) . ? N2 C26 1.341(3) . ? F2 C3 1.336(2) . ? C2 C3 1.380(2) . ? F3 C4 1.346(2) . ? C3 C4 1.368(3) . ? F4 C5 1.344(2) . ? C4 C5 1.346(3) . ? F5 C6 1.348(2) . ? C5 C6 1.391(2) . ? F6 C8 1.3464(17) . ? F7 C9 1.3412(17) . ? C7 C12 1.383(2) . ? C7 C8 1.395(2) . ? F8 C10 1.3371(17) . ? C8 C9 1.373(2) . ? F9 C11 1.3410(18) . ? C9 C10 1.369(2) . ? F10 C12 1.3474(17) . ? C10 C11 1.373(2) . ? F11 C14 1.3503(19) . ? C11 C12 1.386(2) . ? F12 C15 1.334(2) . ? F13 C16 1.332(2) . ? C13 C14 1.385(2) . ? C13 C18 1.391(2) . ? F14 C17 1.337(2) . ? C14 C15 1.379(2) . ? F15 C18 1.3547(18) . ? C15 C16 1.370(3) . ? C16 C17 1.365(3) . ? C17 C18 1.377(2) . ? C19 C20 1.374(2) . ? C19 C30 1.485(2) . ? C20 C21 1.390(2) . ? C21 C22 1.389(2) . ? C21 C24 1.482(2) . ? C22 C23 1.376(2) . ? C23 C29 1.483(2) . ? C24 C25 1.378(2) . ? C24 C28 1.387(2) . ? C25 C26 1.392(2) . ? C26 C32 1.496(3) . ? C27 C28 1.387(2) . ? C27 C31 1.501(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 N1 O1 B1 118.51(10) . . ? C19 N1 C23 123.76(12) . . ? C19 N1 O1 117.99(11) . . ? C23 N1 O1 117.85(11) . . ? O1 B1 C13 109.60(11) . . ? O1 B1 C1 106.99(11) . . ? C13 B1 C1 116.40(13) . . ? O1 B1 C7 107.89(11) . . ? C13 B1 C7 113.04(11) . . ? C1 B1 C7 102.35(12) . . ? C6 C1 C2 113.49(15) . . ? C6 C1 B1 127.33(15) . . ? C2 C1 B1 118.93(14) . . ? C27 N2 C26 118.33(15) . . ? F1 C2 C3 115.93(16) . . ? F1 C2 C1 119.59(14) . . ? C3 C2 C1 124.46(17) . . ? F2 C3 C4 120.64(16) . . ? F2 C3 C2 120.53(18) . . ? C4 C3 C2 118.83(18) . . ? C5 C4 F3 120.44(19) . . ? C5 C4 C3 119.63(16) . . ? F3 C4 C3 119.9(2) . . ? F4 C5 C4 119.83(17) . . ? F4 C5 C6 119.74(19) . . ? C4 C5 C6 120.42(17) . . ? F5 C6 C1 121.03(15) . . ? F5 C6 C5 115.84(15) . . ? C1 C6 C5 123.13(18) . . ? C12 C7 C8 113.49(13) . . ? C12 C7 B1 128.23(13) . . ? C8 C7 B1 117.93(12) . . ? F6 C8 C9 116.44(12) . . ? F6 C8 C7 118.88(12) . . ? C9 C8 C7 124.67(14) . . ? F7 C9 C10 119.69(13) . . ? F7 C9 C8 121.01(14) . . ? C10 C9 C8 119.30(13) . . ? F8 C10 C9 120.17(13) . . ? F8 C10 C11 120.85(14) . . ? C9 C10 C11 118.97(13) . . ? F9 C11 C10 119.42(13) . . ? F9 C11 C12 120.50(14) . . ? C10 C11 C12 120.08(14) . . ? F10 C12 C7 121.08(13) . . ? F10 C12 C11 115.44(13) . . ? C7 C12 C11 123.48(14) . . ? C14 C13 C18 112.56(14) . . ? C14 C13 B1 122.40(13) . . ? C18 C13 B1 125.00(13) . . ? F11 C14 C15 115.47(14) . . ? F11 C14 C13 119.83(15) . . ? C15 C14 C13 124.70(15) . . ? F12 C15 C16 120.29(16) . . ? F12 C15 C14 120.21(17) . . ? C16 C15 C14 119.49(16) . . ? F13 C16 C17 120.28(17) . . ? F13 C16 C15 120.74(17) . . ? C17 C16 C15 118.96(15) . . ? F14 C17 C16 120.22(16) . . ? F14 C17 C18 120.22(16) . . ? C16 C17 C18 119.56(16) . . ? F15 C18 C17 114.35(14) . . ? F15 C18 C13 120.96(14) . . ? C17 C18 C13 124.69(15) . . ? N1 C19 C20 117.85(13) . . ? N1 C19 C30 119.38(13) . . ? C20 C19 C30 122.61(14) . . ? C19 C20 C21 121.58(14) . . ? C22 C21 C20 117.53(14) . . ? C22 C21 C24 121.75(13) . . ? C20 C21 C24 120.66(14) . . ? C23 C22 C21 121.73(13) . . ? N1 C23 C22 117.35(13) . . ? N1 C23 C29 119.27(13) . . ? C22 C23 C29 123.22(13) . . ? C25 C24 C28 118.09(15) . . ? C25 C24 C21 121.10(14) . . ? C28 C24 C21 120.81(15) . . ? C24 C25 C26 119.72(17) . . ? N2 C26 C25 122.02(18) . . ? N2 C26 C32 116.86(17) . . ? C25 C26 C32 121.12(19) . . ? N2 C27 C28 122.58(17) . . ? N2 C27 C31 116.66(18) . . ? C28 C27 C31 120.8(2) . . ? C24 C28 C27 119.25(17) . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.345 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.048 # Attachment '- 6-SJG92_0m.cif' data_sjg92_0m _database_code_depnum_ccdc_archive 'CCDC 846347' #TrackingRef '- 6-SJG92_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H5 B F18 N2' _chemical_formula_weight 674.11 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8877(10) _cell_length_b 11.1457(12) _cell_length_c 12.4221(12) _cell_angle_alpha 74.787(5) _cell_angle_beta 70.681(6) _cell_angle_gamma 77.611(5) _cell_volume 1234.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5606 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 21.72 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.814 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 0.203 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6770 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 20118 _diffrn_reflns_av_R_equivalents 0.0620 _diffrn_reflns_av_sigmaI/netI 0.0803 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 27.58 _reflns_number_total 5606 _reflns_number_gt 2902 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0432P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5606 _refine_ls_number_parameters 414 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1154 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1082 _refine_ls_wR_factor_gt 0.0864 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.958 _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 0.2872(3) 0.7192(3) 0.2556(2) 0.0261(6) Uani 1 1 d . . . N1 N 0.2194(2) 0.5953(2) 0.28791(17) 0.0266(5) Uani 1 1 d . . . N2 N 0.0706(2) 0.6639(2) 0.16795(17) 0.0269(5) Uani 1 1 d . . . F2 F 0.32975(16) 0.97970(13) 0.18851(12) 0.0452(4) Uani 1 1 d . . . F3 F 0.14397(18) 1.17632(14) 0.25657(14) 0.0566(5) Uani 1 1 d . . . F4 F -0.12625(18) 1.14623(15) 0.40091(15) 0.0622(5) Uani 1 1 d . . . F5 F -0.20428(15) 0.91146(15) 0.48315(13) 0.0533(4) Uani 1 1 d . . . F6 F -0.02300(14) 0.71439(13) 0.41992(11) 0.0364(4) Uani 1 1 d . . . F8 F 0.21309(17) 0.90429(14) 0.04487(12) 0.0495(4) Uani 1 1 d . . . F9 F 0.3595(2) 0.90670(18) -0.17682(14) 0.0785(6) Uani 1 1 d . . . F10 F 0.5953(2) 0.7308(2) -0.23554(13) 0.0823(6) Uani 1 1 d . . . F11 F 0.68352(17) 0.55759(17) -0.06355(14) 0.0656(5) Uani 1 1 d . . . F12 F 0.53961(15) 0.55492(14) 0.15764(13) 0.0460(4) Uani 1 1 d . . . F14 F 0.22671(14) 0.61261(14) 0.50403(11) 0.0404(4) Uani 1 1 d . . . F15 F 0.39275(17) 0.59279(14) 0.63947(12) 0.0504(4) Uani 1 1 d . . . F16 F 0.66043(17) 0.66656(15) 0.54763(13) 0.0531(4) Uani 1 1 d . . . F17 F 0.74978(16) 0.77505(16) 0.31599(13) 0.0534(4) Uani 1 1 d . . . F18 F 0.58646(15) 0.79943(14) 0.18027(11) 0.0440(4) Uani 1 1 d . . . F19 F 0.05912(18) 0.76263(17) -0.07035(13) 0.0662(5) Uani 1 1 d . . . F20 F -0.16630(18) 0.74234(17) -0.00908(14) 0.0649(5) Uani 1 1 d . . . F21 F -0.0868(2) 0.86357(16) 0.05696(15) 0.0664(5) Uani 1 1 d . . . C1 C 0.1619(2) 0.8367(2) 0.29369(19) 0.0273(6) Uani 1 1 d . . . C2 C 0.1959(3) 0.9591(2) 0.2592(2) 0.0325(6) Uani 1 1 d . . . C3 C 0.1029(3) 1.0613(2) 0.2935(2) 0.0390(7) Uani 1 1 d . . . C4 C -0.0336(3) 1.0464(3) 0.3664(2) 0.0407(7) Uani 1 1 d . . . C5 C -0.0734(3) 0.9288(3) 0.4072(2) 0.0350(6) Uani 1 1 d . . . C6 C 0.0243(3) 0.8277(2) 0.3714(2) 0.0292(6) Uani 1 1 d . . . C7 C 0.3732(3) 0.7344(2) 0.1139(2) 0.0296(6) Uani 1 1 d . . . C8 C 0.3352(3) 0.8191(3) 0.0224(2) 0.0379(7) Uani 1 1 d . . . C9 C 0.4068(3) 0.8209(3) -0.0940(2) 0.0493(8) Uani 1 1 d . . . C10 C 0.5250(3) 0.7332(3) -0.1229(2) 0.0529(9) Uani 1 1 d . . . C11 C 0.5672(3) 0.6450(3) -0.0362(2) 0.0453(8) Uani 1 1 d . . . C12 C 0.4918(3) 0.6468(2) 0.0774(2) 0.0342(6) Uani 1 1 d . . . C13 C 0.3982(2) 0.7036(2) 0.33357(19) 0.0266(6) Uani 1 1 d . . . C14 C 0.3577(3) 0.6542(2) 0.4528(2) 0.0298(6) Uani 1 1 d . . . C15 C 0.4408(3) 0.6433(2) 0.5250(2) 0.0336(6) Uani 1 1 d . . . C16 C 0.5744(3) 0.6814(2) 0.4792(2) 0.0361(6) Uani 1 1 d . . . C17 C 0.6197(3) 0.7342(2) 0.3629(2) 0.0359(6) Uani 1 1 d . . . C18 C 0.5320(3) 0.7454(2) 0.2937(2) 0.0317(6) Uani 1 1 d . . . C19 C 0.1207(2) 0.5733(2) 0.24836(19) 0.0250(5) Uani 1 1 d . . . C20 C 0.0598(3) 0.4596(2) 0.2849(2) 0.0302(6) Uani 1 1 d . . . H20A H 0.0899 0.3935 0.3418 0.036 Uiso 1 1 calc R . . C21 C -0.0407(3) 0.4448(2) 0.2392(2) 0.0364(6) Uani 1 1 d . . . H21A H -0.0819 0.3689 0.2658 0.044 Uiso 1 1 calc R . . C22 C -0.0855(3) 0.5404(3) 0.1523(2) 0.0363(6) Uani 1 1 d . . . H22A H -0.1541 0.5289 0.1187 0.044 Uiso 1 1 calc R . . C23 C -0.0281(3) 0.6473(2) 0.1190(2) 0.0308(6) Uani 1 1 d . . . C24 C -0.0566(3) 0.7537(3) 0.0246(2) 0.0449(7) Uani 1 1 d . . . H2 H 0.096(3) 0.736(2) 0.146(2) 0.032(8) Uiso 1 1 d . . . H1 H 0.241(3) 0.536(2) 0.340(2) 0.045(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0257(15) 0.0269(16) 0.0260(14) -0.0022(12) -0.0091(12) -0.0057(12) N1 0.0297(12) 0.0253(12) 0.0264(11) -0.0045(10) -0.0120(9) -0.0023(10) N2 0.0307(12) 0.0219(13) 0.0300(11) -0.0038(10) -0.0106(9) -0.0070(10) F2 0.0436(9) 0.0369(9) 0.0516(9) -0.0075(7) -0.0048(8) -0.0151(7) F3 0.0771(12) 0.0276(9) 0.0671(11) -0.0113(8) -0.0212(9) -0.0092(8) F4 0.0657(11) 0.0435(10) 0.0727(12) -0.0295(9) -0.0152(9) 0.0160(9) F5 0.0338(9) 0.0629(12) 0.0591(10) -0.0284(9) -0.0004(8) 0.0002(8) F6 0.0306(8) 0.0348(9) 0.0412(8) -0.0086(7) -0.0051(6) -0.0070(7) F8 0.0596(11) 0.0455(10) 0.0394(9) 0.0032(7) -0.0229(8) -0.0004(8) F9 0.1069(15) 0.0936(15) 0.0321(9) 0.0135(9) -0.0260(10) -0.0316(12) F10 0.0827(13) 0.1371(18) 0.0312(9) -0.0324(10) 0.0115(9) -0.0499(13) F11 0.0436(10) 0.0905(14) 0.0670(11) -0.0535(10) 0.0078(9) -0.0105(9) F12 0.0407(9) 0.0483(10) 0.0492(9) -0.0197(8) -0.0140(7) 0.0070(7) F14 0.0346(8) 0.0575(10) 0.0289(8) -0.0069(7) -0.0050(6) -0.0152(7) F15 0.0594(10) 0.0654(12) 0.0287(8) -0.0024(7) -0.0183(7) -0.0140(9) F16 0.0518(10) 0.0723(12) 0.0493(10) -0.0163(8) -0.0319(8) -0.0059(9) F17 0.0358(9) 0.0856(13) 0.0493(9) -0.0211(9) -0.0130(8) -0.0205(9) F18 0.0406(9) 0.0659(11) 0.0297(8) -0.0057(7) -0.0081(7) -0.0249(8) F19 0.0564(11) 0.0957(15) 0.0371(9) 0.0094(9) -0.0116(8) -0.0229(10) F20 0.0546(11) 0.0942(14) 0.0548(10) 0.0037(9) -0.0358(9) -0.0208(10) F21 0.0887(14) 0.0419(11) 0.0730(12) 0.0027(9) -0.0470(11) 0.0013(10) C1 0.0319(14) 0.0280(15) 0.0265(12) -0.0056(11) -0.0146(11) -0.0039(11) C2 0.0333(15) 0.0336(16) 0.0319(14) -0.0066(12) -0.0094(12) -0.0081(12) C3 0.0525(18) 0.0280(16) 0.0417(16) -0.0100(13) -0.0188(14) -0.0051(14) C4 0.0481(18) 0.0306(17) 0.0478(16) -0.0197(13) -0.0201(14) 0.0098(14) C5 0.0291(15) 0.0437(18) 0.0325(14) -0.0152(12) -0.0082(12) 0.0021(13) C6 0.0295(14) 0.0314(15) 0.0288(13) -0.0082(11) -0.0106(11) -0.0027(12) C7 0.0307(14) 0.0327(15) 0.0304(13) -0.0085(11) -0.0101(11) -0.0102(12) C8 0.0405(16) 0.0421(17) 0.0337(15) -0.0067(13) -0.0120(12) -0.0104(14) C9 0.062(2) 0.065(2) 0.0242(14) 0.0023(14) -0.0122(14) -0.0311(18) C10 0.0511(19) 0.086(3) 0.0270(15) -0.0220(16) 0.0069(14) -0.0363(19) C11 0.0336(16) 0.064(2) 0.0425(17) -0.0273(16) 0.0014(13) -0.0158(15) C12 0.0306(14) 0.0438(17) 0.0343(14) -0.0154(13) -0.0089(12) -0.0095(13) C13 0.0248(13) 0.0282(14) 0.0285(13) -0.0116(11) -0.0079(10) -0.0004(11) C14 0.0290(14) 0.0325(15) 0.0286(13) -0.0087(11) -0.0084(11) -0.0030(11) C15 0.0400(16) 0.0365(16) 0.0227(13) -0.0071(11) -0.0086(12) -0.0019(12) C16 0.0381(16) 0.0463(17) 0.0360(15) -0.0184(13) -0.0235(13) 0.0016(13) C17 0.0255(14) 0.0470(18) 0.0399(15) -0.0171(13) -0.0097(12) -0.0048(12) C18 0.0327(15) 0.0388(16) 0.0257(13) -0.0083(11) -0.0096(11) -0.0055(12) C19 0.0263(13) 0.0237(14) 0.0225(12) -0.0082(10) -0.0024(10) -0.0019(11) C20 0.0328(14) 0.0255(15) 0.0289(13) -0.0043(11) -0.0046(11) -0.0061(11) C21 0.0369(15) 0.0323(16) 0.0393(15) -0.0107(12) -0.0036(13) -0.0118(12) C22 0.0315(15) 0.0456(18) 0.0383(15) -0.0138(13) -0.0087(12) -0.0149(13) C23 0.0259(13) 0.0409(16) 0.0282(13) -0.0113(12) -0.0082(11) -0.0049(12) C24 0.0408(17) 0.056(2) 0.0410(17) -0.0011(15) -0.0186(14) -0.0134(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 N1 1.564(3) . ? B1 C1 1.647(4) . ? B1 C13 1.645(3) . ? B1 C7 1.663(3) . ? N1 C19 1.318(3) . ? N2 C19 1.359(3) . ? N2 C23 1.373(3) . ? F2 C2 1.353(3) . ? F3 C3 1.346(3) . ? F4 C4 1.347(3) . ? F5 C5 1.344(3) . ? F6 C6 1.358(3) . ? F8 C8 1.364(3) . ? F9 C9 1.342(3) . ? F10 C10 1.345(3) . ? F11 C11 1.349(3) . ? F12 C12 1.355(3) . ? F14 C14 1.362(3) . ? F15 C15 1.346(3) . ? F16 C16 1.348(3) . ? F17 C17 1.348(3) . ? F18 C18 1.352(3) . ? F19 C24 1.343(3) . ? F20 C24 1.325(3) . ? F21 C24 1.331(3) . ? C1 C6 1.390(3) . ? C1 C2 1.397(3) . ? C2 C3 1.368(3) . ? C3 C4 1.371(4) . ? C4 C5 1.368(4) . ? C5 C6 1.382(3) . ? C7 C8 1.376(3) . ? C7 C12 1.386(3) . ? C8 C9 1.381(4) . ? C9 C10 1.367(4) . ? C10 C11 1.366(4) . ? C11 C12 1.364(3) . ? C13 C18 1.386(3) . ? C13 C14 1.389(3) . ? C14 C15 1.372(3) . ? C15 C16 1.366(4) . ? C16 C17 1.369(3) . ? C17 C18 1.378(3) . ? C19 C20 1.421(3) . ? C20 C21 1.353(3) . ? C21 C22 1.417(4) . ? C22 C23 1.338(3) . ? C23 C24 1.485(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 N1 B1 C1 110.74(19) . . ? N1 B1 C13 109.21(19) . . ? C1 B1 C13 104.71(18) . . ? N1 B1 C7 103.96(19) . . ? C1 B1 C7 115.98(19) . . ? C13 B1 C7 112.23(19) . . ? C19 N1 B1 127.4(2) . . ? C19 N2 C23 123.2(2) . . ? C6 C1 C2 112.9(2) . . ? C6 C1 B1 126.7(2) . . ? C2 C1 B1 120.0(2) . . ? F2 C2 C3 116.8(2) . . ? F2 C2 C1 118.9(2) . . ? C3 C2 C1 124.3(2) . . ? F3 C3 C2 120.8(2) . . ? F3 C3 C4 119.6(2) . . ? C2 C3 C4 119.7(2) . . ? F4 C4 C5 120.2(3) . . ? F4 C4 C3 120.3(3) . . ? C5 C4 C3 119.5(2) . . ? F5 C5 C4 120.4(2) . . ? F5 C5 C6 120.5(2) . . ? C4 C5 C6 119.1(2) . . ? F6 C6 C5 114.7(2) . . ? F6 C6 C1 120.8(2) . . ? C5 C6 C1 124.5(2) . . ? C8 C7 C12 112.7(2) . . ? C8 C7 B1 128.1(2) . . ? C12 C7 B1 118.9(2) . . ? F8 C8 C7 119.3(2) . . ? F8 C8 C9 115.7(2) . . ? C7 C8 C9 124.9(3) . . ? F9 C9 C10 120.9(3) . . ? F9 C9 C8 120.2(3) . . ? C10 C9 C8 118.8(3) . . ? F10 C10 C9 120.3(3) . . ? F10 C10 C11 120.5(3) . . ? C9 C10 C11 119.2(3) . . ? F11 C11 C12 120.6(3) . . ? F11 C11 C10 119.9(3) . . ? C12 C11 C10 119.5(3) . . ? F12 C12 C11 115.7(2) . . ? F12 C12 C7 119.6(2) . . ? C11 C12 C7 124.8(3) . . ? C18 C13 C14 112.9(2) . . ? C18 C13 B1 125.9(2) . . ? C14 C13 B1 121.0(2) . . ? F14 C14 C15 116.2(2) . . ? F14 C14 C13 119.0(2) . . ? C15 C14 C13 124.8(2) . . ? F15 C15 C16 120.2(2) . . ? F15 C15 C14 120.4(2) . . ? C16 C15 C14 119.4(2) . . ? F16 C16 C15 120.4(2) . . ? F16 C16 C17 120.6(2) . . ? C15 C16 C17 119.0(2) . . ? F17 C17 C16 120.2(2) . . ? F17 C17 C18 120.0(2) . . ? C16 C17 C18 119.8(2) . . ? F18 C18 C17 115.1(2) . . ? F18 C18 C13 120.8(2) . . ? C17 C18 C13 124.1(2) . . ? N1 C19 N2 119.4(2) . . ? N1 C19 C20 124.4(2) . . ? N2 C19 C20 116.3(2) . . ? C21 C20 C19 120.4(2) . . ? C20 C21 C22 121.2(2) . . ? C23 C22 C21 117.9(2) . . ? C22 C23 N2 121.0(2) . . ? C22 C23 C24 124.8(2) . . ? N2 C23 C24 114.1(2) . . ? F20 C24 F21 107.4(2) . . ? F20 C24 F19 107.0(2) . . ? F21 C24 F19 106.2(2) . . ? F20 C24 C23 112.3(2) . . ? F21 C24 C23 112.0(2) . . ? F19 C24 C23 111.5(2) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.210 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.054 # Attachment '- 7-CBC014_0m.cif' data_cbc014_0m _database_code_depnum_ccdc_archive 'CCDC 846348' #TrackingRef '- 7-CBC014_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H8 B F15 N2' _chemical_formula_weight 656.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8040(3) _cell_length_b 9.9703(4) _cell_length_c 14.3432(5) _cell_angle_alpha 90.240(2) _cell_angle_beta 109.000(2) _cell_angle_gamma 113.800(2) _cell_volume 1197.93(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5435 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.819 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.189 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6476 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 18932 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.53 _reflns_number_total 5435 _reflns_number_gt 4459 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0478P)^2^+0.8889P] 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 5435 _refine_ls_number_parameters 406 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0930 _refine_ls_wR_factor_gt 0.0864 _refine_ls_goodness_of_fit_ref 0.893 _refine_ls_restrained_S_all 0.893 _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 C6 C 0.1095(2) -0.02164(18) 0.14744(15) 0.0363(4) Uani 1 1 d . . . H6A H 0.0559 -0.1266 0.1296 0.044 Uiso 1 1 calc R . . C8 C 0.2708(2) 0.21652(18) 0.11439(13) 0.0297(3) Uani 1 1 d . . . H8A H 0.3273 0.2744 0.0753 0.036 Uiso 1 1 calc R . . C9 C 0.26385(17) 0.28422(16) 0.19690(11) 0.0215(3) Uani 1 1 d . . . C1 C 0.34335(17) 0.51263(16) 0.30285(11) 0.0200(3) Uani 1 1 d . . . C16 C 0.39422(17) 0.74995(15) 0.14555(11) 0.0201(3) Uani 1 1 d . . . C17 C 0.45421(17) 0.80152(16) 0.07021(11) 0.0225(3) Uani 1 1 d . . . C18 C 0.36145(19) 0.79679(17) -0.02641(11) 0.0246(3) Uani 1 1 d . . . C19 C 0.19774(19) 0.74030(16) -0.05330(11) 0.0249(3) Uani 1 1 d . . . C25 C 0.6326(2) 1.23744(17) 0.38156(11) 0.0272(3) Uani 1 1 d . . . C26 C 0.50509(19) 1.12180(18) 0.39219(11) 0.0253(3) Uani 1 1 d . . . C27 C 0.46875(17) 0.97813(16) 0.35554(11) 0.0222(3) Uani 1 1 d . . . C22 C 0.55805(17) 0.94002(15) 0.31143(10) 0.0188(3) Uani 1 1 d . . . C21 C 0.22916(18) 0.69605(16) 0.11424(11) 0.0214(3) Uani 1 1 d . . . C20 C 0.13215(17) 0.69050(16) 0.01798(11) 0.0234(3) Uani 1 1 d . . . C10 C 0.66752(17) 0.73491(15) 0.27819(11) 0.0202(3) Uani 1 1 d . . . C11 C 0.68504(17) 0.64725(16) 0.21181(11) 0.0224(3) Uani 1 1 d . . . C12 C 0.81264(19) 0.60986(16) 0.23218(12) 0.0259(3) Uani 1 1 d . . . C13 C 0.93219(18) 0.66103(17) 0.32439(13) 0.0265(3) Uani 1 1 d . . . C14 C 0.92116(18) 0.74751(17) 0.39402(12) 0.0265(3) Uani 1 1 d . . . C15 C 0.79116(18) 0.78123(16) 0.37034(11) 0.0232(3) Uani 1 1 d . . . C5 C 0.1038(2) 0.04538(17) 0.22885(13) 0.0305(4) Uani 1 1 d . . . H5A H 0.0466 -0.0135 0.2673 0.037 Uiso 1 1 calc R . . C4 C 0.18194(18) 0.20049(16) 0.25576(11) 0.0233(3) Uani 1 1 d . . . C3 C 0.18207(19) 0.27764(17) 0.34020(12) 0.0257(3) Uani 1 1 d . . . H3A H 0.1254 0.2228 0.3803 0.031 Uiso 1 1 calc R . . C2 C 0.26088(19) 0.42635(17) 0.36393(11) 0.0246(3) Uani 1 1 d . . . H2B H 0.2620 0.4748 0.4216 0.030 Uiso 1 1 calc R . . C23 C 0.68814(18) 1.06213(16) 0.30550(11) 0.0217(3) Uani 1 1 d . . . C24 C 0.72494(19) 1.20783(16) 0.33765(11) 0.0255(3) Uani 1 1 d . . . C7 C 0.1941(2) 0.06411(19) 0.09068(14) 0.0365(4) Uani 1 1 d . . . H7A H 0.1987 0.0166 0.0350 0.044 Uiso 1 1 calc R . . H1A H 0.3875 0.4915 0.1828 0.044 Uiso 1 1 d R . . H2A H 0.4183 0.7006 0.3781 0.044 Uiso 1 1 d R . . F8 F 0.10505(12) 0.73399(12) -0.14633(7) 0.0360(2) Uani 1 1 d . . . F13 F 0.66839(14) 1.37818(11) 0.41521(8) 0.0419(3) Uani 1 1 d . . . F10 F 0.15172(11) 0.64507(11) 0.17813(7) 0.0306(2) Uani 1 1 d . . . F6 F 0.61333(10) 0.86182(11) 0.09028(7) 0.0299(2) Uani 1 1 d . . . F7 F 0.42871(12) 0.84573(12) -0.09486(7) 0.0349(2) Uani 1 1 d . . . F9 F -0.02705(11) 0.63671(11) -0.00601(7) 0.0319(2) Uani 1 1 d . . . F1 F 0.56889(11) 0.58423(10) 0.12033(7) 0.0284(2) Uani 1 1 d . . . F2 F 0.81692(12) 0.52268(11) 0.16295(8) 0.0378(2) Uani 1 1 d . . . F3 F 1.05536(11) 0.62467(11) 0.34781(8) 0.0364(2) Uani 1 1 d . . . F5 F 0.78805(12) 0.86332(11) 0.44426(7) 0.0328(2) Uani 1 1 d . . . F12 F 0.85303(13) 1.31974(10) 0.32998(8) 0.0385(3) Uani 1 1 d . . . F11 F 0.78949(11) 1.04292(10) 0.26811(7) 0.0301(2) Uani 1 1 d . . . F15 F 0.33746(11) 0.87238(10) 0.36697(8) 0.0325(2) Uani 1 1 d . . . F14 F 0.41854(13) 1.14852(11) 0.43970(7) 0.0351(2) Uani 1 1 d . . . F4 F 1.03529(12) 0.79707(12) 0.48492(8) 0.0407(3) Uani 1 1 d . . . N1 N 0.33892(15) 0.43828(13) 0.22246(9) 0.0209(3) Uani 1 1 d . . . N2 N 0.41897(15) 0.65862(13) 0.32261(9) 0.0211(3) Uani 1 1 d . . . B1 B 0.50996(19) 0.76934(17) 0.26293(12) 0.0184(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 C6 0.0386(10) 0.0202(8) 0.0499(11) 0.0001(7) 0.0176(8) 0.0113(7) C8 0.0328(8) 0.0269(8) 0.0326(9) 0.0017(6) 0.0166(7) 0.0121(7) C9 0.0206(7) 0.0212(7) 0.0237(7) 0.0023(6) 0.0065(6) 0.0111(6) C1 0.0203(7) 0.0218(7) 0.0193(7) 0.0038(5) 0.0059(5) 0.0111(6) C16 0.0223(7) 0.0185(7) 0.0192(7) 0.0004(5) 0.0070(6) 0.0089(6) C17 0.0214(7) 0.0217(7) 0.0236(7) 0.0020(6) 0.0082(6) 0.0083(6) C18 0.0316(8) 0.0248(7) 0.0211(7) 0.0061(6) 0.0118(6) 0.0138(6) C19 0.0308(8) 0.0243(7) 0.0192(7) 0.0014(6) 0.0038(6) 0.0156(6) C25 0.0399(9) 0.0203(7) 0.0209(7) -0.0002(6) 0.0061(7) 0.0161(7) C26 0.0319(8) 0.0315(8) 0.0200(7) 0.0022(6) 0.0085(6) 0.0214(7) C27 0.0210(7) 0.0230(7) 0.0220(7) 0.0021(6) 0.0066(6) 0.0098(6) C22 0.0207(7) 0.0203(7) 0.0144(6) 0.0014(5) 0.0035(5) 0.0100(6) C21 0.0239(7) 0.0202(7) 0.0216(7) 0.0028(5) 0.0101(6) 0.0095(6) C20 0.0201(7) 0.0207(7) 0.0270(8) -0.0006(6) 0.0045(6) 0.0095(6) C10 0.0220(7) 0.0183(7) 0.0225(7) 0.0043(5) 0.0093(6) 0.0096(6) C11 0.0208(7) 0.0204(7) 0.0240(7) 0.0012(6) 0.0079(6) 0.0069(6) C12 0.0263(8) 0.0208(7) 0.0361(9) 0.0031(6) 0.0178(7) 0.0103(6) C13 0.0193(7) 0.0230(7) 0.0412(9) 0.0105(6) 0.0132(7) 0.0112(6) C14 0.0228(7) 0.0268(8) 0.0256(8) 0.0071(6) 0.0043(6) 0.0100(6) C15 0.0267(7) 0.0228(7) 0.0218(7) 0.0036(6) 0.0090(6) 0.0119(6) C5 0.0322(8) 0.0224(8) 0.0407(9) 0.0082(7) 0.0167(7) 0.0124(7) C4 0.0231(7) 0.0229(7) 0.0272(8) 0.0063(6) 0.0090(6) 0.0130(6) C3 0.0296(8) 0.0263(8) 0.0271(8) 0.0106(6) 0.0151(6) 0.0138(6) C2 0.0303(8) 0.0277(8) 0.0211(7) 0.0055(6) 0.0123(6) 0.0150(6) C23 0.0253(7) 0.0242(7) 0.0184(7) 0.0034(5) 0.0085(6) 0.0127(6) C24 0.0299(8) 0.0193(7) 0.0220(7) 0.0034(6) 0.0072(6) 0.0070(6) C7 0.0416(10) 0.0284(8) 0.0412(10) -0.0047(7) 0.0180(8) 0.0144(8) F8 0.0380(5) 0.0474(6) 0.0220(5) 0.0067(4) 0.0028(4) 0.0239(5) F13 0.0630(7) 0.0224(5) 0.0423(6) -0.0025(4) 0.0203(5) 0.0193(5) F10 0.0231(4) 0.0412(5) 0.0282(5) 0.0088(4) 0.0129(4) 0.0115(4) F6 0.0216(4) 0.0387(5) 0.0263(5) 0.0081(4) 0.0104(4) 0.0084(4) F7 0.0382(5) 0.0480(6) 0.0239(5) 0.0136(4) 0.0161(4) 0.0196(5) F9 0.0203(4) 0.0369(5) 0.0335(5) 0.0019(4) 0.0039(4) 0.0119(4) F1 0.0271(5) 0.0307(5) 0.0248(5) -0.0055(4) 0.0066(4) 0.0120(4) F2 0.0355(5) 0.0364(5) 0.0478(6) -0.0063(5) 0.0185(5) 0.0185(5) F3 0.0246(5) 0.0347(5) 0.0564(7) 0.0114(5) 0.0158(5) 0.0178(4) F5 0.0380(5) 0.0417(6) 0.0201(4) -0.0026(4) 0.0039(4) 0.0237(5) F12 0.0456(6) 0.0201(5) 0.0457(6) 0.0039(4) 0.0241(5) 0.0039(4) F11 0.0329(5) 0.0251(5) 0.0382(5) 0.0049(4) 0.0226(4) 0.0105(4) F15 0.0268(5) 0.0291(5) 0.0469(6) 0.0027(4) 0.0207(4) 0.0112(4) F14 0.0446(6) 0.0410(6) 0.0343(5) 0.0020(4) 0.0186(5) 0.0289(5) F4 0.0328(5) 0.0513(6) 0.0315(5) 0.0023(5) -0.0027(4) 0.0228(5) N1 0.0243(6) 0.0191(6) 0.0208(6) 0.0036(5) 0.0106(5) 0.0086(5) N2 0.0256(6) 0.0212(6) 0.0175(6) 0.0016(5) 0.0088(5) 0.0103(5) B1 0.0191(7) 0.0183(7) 0.0174(7) 0.0009(6) 0.0061(6) 0.0081(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C6 C5 1.371(2) . ? C6 C7 1.398(3) . ? C6 H6A 0.9500 . ? C8 C7 1.377(2) . ? C8 C9 1.394(2) . ? C8 H8A 0.9500 . ? C9 N1 1.3937(18) . ? C9 C4 1.400(2) . ? C1 N2 1.3181(19) . ? C1 N1 1.3472(19) . ? C1 C2 1.438(2) . ? C16 C21 1.390(2) . ? C16 C17 1.397(2) . ? C16 B1 1.654(2) . ? C17 F6 1.3518(17) . ? C17 C18 1.376(2) . ? C18 F7 1.3426(17) . ? C18 C19 1.381(2) . ? C19 F8 1.3319(17) . ? C19 C20 1.371(2) . ? C25 F13 1.3460(17) . ? C25 C26 1.370(2) . ? C25 C24 1.374(2) . ? C26 F14 1.3464(17) . ? C26 C27 1.384(2) . ? C27 F15 1.3560(17) . ? C27 C22 1.392(2) . ? C22 C23 1.391(2) . ? C22 B1 1.653(2) . ? C21 F10 1.3491(16) . ? C21 C20 1.384(2) . ? C20 F9 1.3474(17) . ? C10 C11 1.386(2) . ? C10 C15 1.389(2) . ? C10 B1 1.661(2) . ? C11 F1 1.3624(17) . ? C11 C12 1.389(2) . ? C12 F2 1.3389(18) . ? C12 C13 1.373(2) . ? C13 F3 1.3389(17) . ? C13 C14 1.375(2) . ? C14 F4 1.3396(18) . ? C14 C15 1.385(2) . ? C15 F5 1.3523(17) . ? C5 C4 1.405(2) . ? C5 H5A 0.9500 . ? C4 C3 1.431(2) . ? C3 C2 1.346(2) . ? C3 H3A 0.9500 . ? C2 H2B 0.9500 . ? C23 F11 1.3459(17) . ? C23 C24 1.384(2) . ? C24 F12 1.3394(18) . ? C7 H7A 0.9500 . ? N1 H1A 0.8978 . ? N2 B1 1.5676(19) . ? N2 H2A 0.9003 . ? 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 C6 C7 120.13(15) . . ? C5 C6 H6A 119.9 . . ? C7 C6 H6A 119.9 . . ? C7 C8 C9 118.74(15) . . ? C7 C8 H8A 120.6 . . ? C9 C8 H8A 120.6 . . ? N1 C9 C8 120.23(14) . . ? N1 C9 C4 118.42(13) . . ? C8 C9 C4 121.36(14) . . ? N2 C1 N1 120.47(13) . . ? N2 C1 C2 122.28(13) . . ? N1 C1 C2 117.25(13) . . ? C21 C16 C17 113.17(13) . . ? C21 C16 B1 123.44(13) . . ? C17 C16 B1 123.03(13) . . ? F6 C17 C18 115.57(13) . . ? F6 C17 C16 120.02(13) . . ? C18 C17 C16 124.41(14) . . ? F7 C18 C17 120.55(14) . . ? F7 C18 C19 119.76(13) . . ? C17 C18 C19 119.69(14) . . ? F8 C19 C20 120.48(14) . . ? F8 C19 C18 120.98(14) . . ? C20 C19 C18 118.54(14) . . ? F13 C25 C26 120.32(15) . . ? F13 C25 C24 120.45(15) . . ? C26 C25 C24 119.22(14) . . ? F14 C26 C25 119.90(14) . . ? F14 C26 C27 120.70(15) . . ? C25 C26 C27 119.39(14) . . ? F15 C27 C26 114.72(13) . . ? F15 C27 C22 120.89(13) . . ? C26 C27 C22 124.39(14) . . ? C23 C22 C27 113.22(13) . . ? C23 C22 B1 122.29(13) . . ? C27 C22 B1 124.36(13) . . ? F10 C21 C20 114.94(13) . . ? F10 C21 C16 121.02(13) . . ? C20 C21 C16 124.04(14) . . ? F9 C20 C19 119.70(13) . . ? F9 C20 C21 120.17(14) . . ? C19 C20 C21 120.13(14) . . ? C11 C10 C15 112.93(13) . . ? C11 C10 B1 127.19(13) . . ? C15 C10 B1 119.41(12) . . ? F1 C11 C10 120.48(13) . . ? F1 C11 C12 114.56(13) . . ? C10 C11 C12 124.88(14) . . ? F2 C12 C13 120.65(14) . . ? F2 C12 C11 120.06(14) . . ? C13 C12 C11 119.27(14) . . ? F3 C13 C12 121.13(15) . . ? F3 C13 C14 120.13(14) . . ? C12 C13 C14 118.71(14) . . ? F4 C14 C13 119.77(14) . . ? F4 C14 C15 120.33(15) . . ? C13 C14 C15 119.89(14) . . ? F5 C15 C14 115.81(13) . . ? F5 C15 C10 119.89(13) . . ? C14 C15 C10 124.30(14) . . ? C6 C5 C4 120.46(15) . . ? C6 C5 H5A 119.8 . . ? C4 C5 H5A 119.8 . . ? C9 C4 C5 118.38(14) . . ? C9 C4 C3 118.18(13) . . ? C5 C4 C3 123.43(14) . . ? C2 C3 C4 121.26(14) . . ? C2 C3 H3A 119.4 . . ? C4 C3 H3A 119.4 . . ? C3 C2 C1 120.60(14) . . ? C3 C2 H2B 119.7 . . ? C1 C2 H2B 119.7 . . ? F11 C23 C24 115.57(13) . . ? F11 C23 C22 120.25(13) . . ? C24 C23 C22 124.17(14) . . ? F12 C24 C25 119.68(14) . . ? F12 C24 C23 120.73(14) . . ? C25 C24 C23 119.53(14) . . ? C8 C7 C6 120.91(16) . . ? C8 C7 H7A 119.5 . . ? C6 C7 H7A 119.5 . . ? C1 N1 C9 124.23(12) . . ? C1 N1 H1A 117.8 . . ? C9 N1 H1A 118.0 . . ? C1 N2 B1 128.97(12) . . ? C1 N2 H2A 115.5 . . ? B1 N2 H2A 115.5 . . ? N2 B1 C22 108.30(11) . . ? N2 B1 C16 111.98(12) . . ? C22 B1 C16 104.64(11) . . ? N2 B1 C10 103.59(11) . . ? C22 B1 C10 113.24(11) . . ? C16 B1 C10 115.11(12) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.332 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.047 # Attachment '- 11-SJG90_0m.cif' data_sjg90_0m _database_code_depnum_ccdc_archive 'CCDC 846349' #TrackingRef '- 11-SJG90_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H5 B Cl F13 N2' _chemical_formula_weight 542.50 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.2702(3) _cell_length_b 31.6155(10) _cell_length_c 12.3047(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.436(2) _cell_angle_gamma 90.00 _cell_volume 3991.7(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9116 _cell_measurement_theta_min 1.8 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.805 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2128 _exptl_absorpt_coefficient_mu 0.321 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6940 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 35879 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 27.53 _reflns_number_total 9116 _reflns_number_gt 6762 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+2.4343P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9116 _refine_ls_number_parameters 647 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1024 _refine_ls_wR_factor_gt 0.0918 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.9794(2) -0.05453(7) 0.14712(18) 0.0216(5) Uani 1 1 d . . . B2 B -0.0078(2) 0.29789(8) 0.84712(18) 0.0214(5) Uani 1 1 d . . . N1 N 0.99911(17) -0.00657(6) 0.13894(14) 0.0227(4) Uani 1 1 d . . . N2 N 1.21199(16) -0.00651(6) 0.20919(14) 0.0252(4) Uani 1 1 d . . . N3 N -0.03884(16) 0.25048(6) 0.85972(13) 0.0224(4) Uani 1 1 d . . . N4 N -0.24305(16) 0.26198(6) 0.92452(14) 0.0240(4) Uani 1 1 d . . . Cl1 Cl 1.10843(5) -0.079200(16) 0.05683(4) 0.02449(12) Uani 1 1 d . . . Cl2 Cl -0.13875(5) 0.319306(17) 0.74590(4) 0.02865(12) Uani 1 1 d . . . F2 F 0.74934(11) -0.00359(4) 0.04886(10) 0.0316(3) Uani 1 1 d . . . F3 F 0.53349(11) -0.03756(4) -0.04019(11) 0.0340(3) Uani 1 1 d . . . F4 F 0.49758(11) -0.12179(4) -0.04340(11) 0.0347(3) Uani 1 1 d . . . F5 F 0.68345(13) -0.17357(4) 0.04983(12) 0.0398(3) Uani 1 1 d . . . F6 F 0.89989(12) -0.14117(4) 0.14194(11) 0.0330(3) Uani 1 1 d . . . F8 F 1.17293(14) -0.11764(5) 0.26610(11) 0.0489(4) Uani 1 1 d . . . F9 F 1.17927(15) -0.13273(6) 0.47709(12) 0.0565(4) Uani 1 1 d . . . F10 F 1.01497(17) -0.09295(6) 0.60848(11) 0.0627(5) Uani 1 1 d . . . F11 F 0.83957(17) -0.03613(6) 0.52245(12) 0.0657(5) Uani 1 1 d . . . F12 F 0.82718(13) -0.02102(5) 0.30904(11) 0.0435(4) Uani 1 1 d . . . F13 F 1.45970(19) -0.04171(7) 0.20848(16) 0.0812(6) Uani 1 1 d . . . F14 F 1.53354(18) 0.00352(7) 0.3200(3) 0.1202(10) Uani 1 1 d . . . F15 F 1.39653(19) -0.04174(8) 0.36653(17) 0.0920(7) Uani 1 1 d . . . F20 F 0.20754(12) 0.23678(4) 0.78363(11) 0.0362(3) Uani 1 1 d . . . F21 F 0.43205(14) 0.26013(5) 0.70367(13) 0.0510(4) Uani 1 1 d . . . F22 F 0.48526(12) 0.34289(5) 0.66740(11) 0.0429(3) Uani 1 1 d . . . F23 F 0.30485(13) 0.40262(4) 0.71327(11) 0.0394(3) Uani 1 1 d . . . F24 F 0.08363(12) 0.38061(4) 0.80186(11) 0.0342(3) Uani 1 1 d . . . F26 F 0.16088(11) 0.27157(4) 1.01570(10) 0.0314(3) Uani 1 1 d . . . F27 F 0.18288(13) 0.29830(5) 1.21962(10) 0.0397(3) Uani 1 1 d . . . F28 F 0.02658(14) 0.36118(5) 1.29022(10) 0.0448(4) Uani 1 1 d . . . F29 F -0.15528(15) 0.39581(5) 1.14965(12) 0.0500(4) Uani 1 1 d . . . F30 F -0.18162(13) 0.36920(4) 0.94566(11) 0.0408(3) Uani 1 1 d . . . F31 F -0.40793(19) 0.30607(6) 1.08298(14) 0.0768(6) Uani 1 1 d . . . F32 F -0.56495(16) 0.27045(6) 1.0078(2) 0.1008(9) Uani 1 1 d . . . F33 F -0.45430(16) 0.31271(5) 0.91670(14) 0.0585(4) Uani 1 1 d . . . C1 C 0.83876(19) -0.07073(6) 0.09744(16) 0.0217(4) Uani 1 1 d . . . C2 C 0.73896(19) -0.04639(6) 0.05195(16) 0.0225(4) Uani 1 1 d . . . C3 C 0.62532(19) -0.06267(7) 0.00496(16) 0.0241(4) Uani 1 1 d . . . C4 C 0.60710(19) -0.10554(7) 0.00278(17) 0.0252(4) Uani 1 1 d . . . C5 C 0.7015(2) -0.13164(7) 0.04907(17) 0.0269(5) Uani 1 1 d . . . C6 C 0.81275(19) -0.11388(7) 0.09588(17) 0.0255(4) Uani 1 1 d . . . C7 C 0.99924(19) -0.06826(7) 0.27551(16) 0.0235(4) Uani 1 1 d . . . C8 C 1.0861(2) -0.09662(7) 0.32472(17) 0.0288(5) Uani 1 1 d . . . C9 C 1.0924(2) -0.10497(8) 0.43486(18) 0.0355(5) Uani 1 1 d . . . C10 C 1.0096(3) -0.08481(9) 0.50157(18) 0.0399(6) Uani 1 1 d . . . C11 C 0.9213(2) -0.05636(8) 0.45779(19) 0.0385(6) Uani 1 1 d . . . C12 C 0.9176(2) -0.04890(7) 0.34771(18) 0.0302(5) Uani 1 1 d . . . C13 C 1.10260(19) 0.01473(7) 0.17664(15) 0.0222(4) Uani 1 1 d . . . C14 C 1.1068(2) 0.05938(7) 0.18614(16) 0.0255(4) Uani 1 1 d . . . H14A H 1.0340 0.0758 0.1613 0.031 Uiso 1 1 calc R . . C15 C 1.2140(2) 0.07874(7) 0.23049(18) 0.0310(5) Uani 1 1 d . . . H15A H 1.2149 0.1087 0.2374 0.037 Uiso 1 1 calc R . . C16 C 1.3243(2) 0.05527(8) 0.26659(18) 0.0335(5) Uani 1 1 d . . . H16A H 1.3989 0.0689 0.2985 0.040 Uiso 1 1 calc R . . C17 C 1.3207(2) 0.01302(8) 0.25449(18) 0.0302(5) Uani 1 1 d . . . C18 C 1.4294(2) -0.01635(9) 0.2884(2) 0.0436(6) Uani 1 1 d . . . C19 C 0.13188(19) 0.30752(7) 0.79530(15) 0.0224(4) Uani 1 1 d . . . C20 C 0.2266(2) 0.27872(7) 0.76873(16) 0.0259(4) Uani 1 1 d . . . C21 C 0.3444(2) 0.28986(8) 0.72728(18) 0.0310(5) Uani 1 1 d . . . C22 C 0.3718(2) 0.33160(8) 0.70902(17) 0.0300(5) Uani 1 1 d . . . C23 C 0.2814(2) 0.36163(7) 0.73279(17) 0.0280(5) Uani 1 1 d . . . C24 C 0.1657(2) 0.34937(7) 0.77628(16) 0.0247(4) Uani 1 1 d . . . C25 C -0.00939(18) 0.31924(6) 0.96852(15) 0.0207(4) Uani 1 1 d . . . C26 C 0.08089(19) 0.30290(7) 1.04512(16) 0.0233(4) Uani 1 1 d . . . C27 C 0.0945(2) 0.31640(7) 1.15134(16) 0.0266(5) Uani 1 1 d . . . C28 C 0.0153(2) 0.34792(7) 1.18657(16) 0.0295(5) Uani 1 1 d . . . C29 C -0.0761(2) 0.36529(7) 1.11522(18) 0.0313(5) Uani 1 1 d . . . C30 C -0.08643(19) 0.35089(7) 1.00911(17) 0.0257(4) Uani 1 1 d . . . C31 C -0.14465(18) 0.23520(6) 0.90271(15) 0.0210(4) Uani 1 1 d . . . C32 C -0.1636(2) 0.19202(7) 0.92857(16) 0.0244(4) Uani 1 1 d . . . H32A H -0.0976 0.1719 0.9145 0.029 Uiso 1 1 calc R . . C33 C -0.2754(2) 0.17919(7) 0.97325(16) 0.0270(5) Uani 1 1 d . . . H33A H -0.2879 0.1500 0.9881 0.032 Uiso 1 1 calc R . . C34 C -0.3738(2) 0.20854(7) 0.99806(17) 0.0285(5) Uani 1 1 d . . . H34A H -0.4507 0.1997 1.0318 0.034 Uiso 1 1 calc R . . C35 C -0.35502(19) 0.24930(7) 0.97240(17) 0.0271(5) Uani 1 1 d . . . C36 C -0.4471(2) 0.28419(8) 0.9967(2) 0.0382(6) Uani 1 1 d . . . H1 H 0.940(2) 0.0093(7) 0.1162(18) 0.024(6) Uiso 1 1 d . . . H3 H 0.018(2) 0.2331(8) 0.8441(18) 0.029(6) Uiso 1 1 d . . . H2 H 1.216(2) -0.0330(8) 0.194(2) 0.034(7) Uiso 1 1 d . . . H4 H -0.238(2) 0.2858(8) 0.8989(18) 0.022(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0212(10) 0.0198(12) 0.0241(11) -0.0015(9) 0.0039(8) 0.0006(9) B2 0.0202(10) 0.0209(12) 0.0229(11) 0.0014(9) -0.0014(8) 0.0027(9) N1 0.0215(8) 0.0197(9) 0.0269(9) -0.0015(7) 0.0003(7) -0.0008(8) N2 0.0232(8) 0.0215(10) 0.0312(10) -0.0043(8) 0.0025(7) -0.0036(8) N3 0.0204(8) 0.0214(10) 0.0253(9) -0.0008(7) 0.0007(7) 0.0020(8) N4 0.0221(8) 0.0208(10) 0.0289(9) 0.0024(8) -0.0013(7) -0.0003(8) Cl1 0.0258(2) 0.0212(3) 0.0269(2) -0.00229(19) 0.00624(19) -0.0005(2) Cl2 0.0289(2) 0.0300(3) 0.0264(3) 0.0054(2) -0.00542(19) 0.0027(2) F2 0.0278(6) 0.0181(6) 0.0484(8) 0.0019(6) -0.0032(5) -0.0010(5) F3 0.0250(6) 0.0305(7) 0.0461(8) 0.0026(6) -0.0036(5) 0.0031(5) F4 0.0241(6) 0.0345(8) 0.0451(8) -0.0022(6) -0.0039(5) -0.0088(6) F5 0.0376(7) 0.0205(7) 0.0605(9) 0.0020(6) -0.0064(6) -0.0078(6) F6 0.0302(6) 0.0210(7) 0.0472(8) 0.0060(6) -0.0045(5) -0.0003(5) F8 0.0552(9) 0.0603(10) 0.0317(7) 0.0056(7) 0.0087(6) 0.0356(8) F9 0.0611(10) 0.0715(12) 0.0369(8) 0.0164(8) 0.0014(7) 0.0338(9) F10 0.0792(12) 0.0860(13) 0.0235(7) 0.0096(8) 0.0090(7) 0.0276(10) F11 0.0770(11) 0.0871(14) 0.0351(8) 0.0044(8) 0.0265(8) 0.0406(10) F12 0.0417(8) 0.0522(9) 0.0374(7) 0.0064(6) 0.0113(6) 0.0242(7) F13 0.0808(13) 0.0880(15) 0.0748(13) -0.0091(11) 0.0017(10) 0.0524(12) F14 0.0417(10) 0.0763(15) 0.237(3) -0.0168(17) -0.0605(14) 0.0014(10) F15 0.0685(12) 0.1229(19) 0.0850(14) 0.0544(13) 0.0103(11) 0.0392(13) F20 0.0344(7) 0.0226(7) 0.0523(8) -0.0007(6) 0.0110(6) 0.0037(6) F21 0.0369(8) 0.0424(9) 0.0754(11) -0.0062(8) 0.0230(7) 0.0100(7) F22 0.0294(7) 0.0504(9) 0.0498(8) 0.0018(7) 0.0145(6) -0.0056(6) F23 0.0372(7) 0.0319(8) 0.0496(8) 0.0105(6) 0.0066(6) -0.0074(6) F24 0.0325(7) 0.0235(7) 0.0472(8) 0.0041(6) 0.0092(6) 0.0030(6) F26 0.0294(6) 0.0338(8) 0.0306(7) -0.0024(5) -0.0037(5) 0.0121(6) F27 0.0434(8) 0.0478(9) 0.0268(7) 0.0006(6) -0.0118(6) 0.0083(7) F28 0.0544(9) 0.0546(10) 0.0254(7) -0.0118(6) 0.0007(6) 0.0042(7) F29 0.0532(9) 0.0501(10) 0.0469(9) -0.0180(7) 0.0031(7) 0.0231(8) F30 0.0414(8) 0.0422(9) 0.0380(7) -0.0026(6) -0.0066(6) 0.0226(7) F31 0.0924(14) 0.0791(14) 0.0574(11) -0.0291(10) -0.0141(10) 0.0497(11) F32 0.0332(9) 0.0566(12) 0.216(3) 0.0099(14) 0.0474(13) 0.0072(9) F33 0.0608(10) 0.0516(10) 0.0627(10) 0.0070(8) -0.0035(8) 0.0273(8) C1 0.0225(9) 0.0207(11) 0.0222(10) 0.0006(8) 0.0041(7) -0.0018(8) C2 0.0249(10) 0.0167(11) 0.0263(10) -0.0004(8) 0.0057(8) -0.0012(8) C3 0.0203(9) 0.0246(12) 0.0277(10) 0.0011(9) 0.0042(8) 0.0027(9) C4 0.0218(10) 0.0272(12) 0.0268(11) -0.0017(9) 0.0032(8) -0.0059(9) C5 0.0297(11) 0.0172(11) 0.0340(11) -0.0010(9) 0.0048(9) -0.0055(9) C6 0.0237(10) 0.0240(12) 0.0288(11) 0.0024(9) 0.0025(8) 0.0006(9) C7 0.0235(10) 0.0211(11) 0.0262(10) -0.0012(8) 0.0028(8) -0.0034(8) C8 0.0296(11) 0.0290(12) 0.0279(11) -0.0021(9) 0.0041(9) 0.0048(10) C9 0.0380(12) 0.0382(14) 0.0302(12) 0.0062(10) 0.0007(10) 0.0095(11) C10 0.0485(14) 0.0504(16) 0.0211(11) 0.0046(10) 0.0061(10) 0.0060(12) C11 0.0418(13) 0.0451(16) 0.0297(12) -0.0012(11) 0.0137(10) 0.0093(12) C12 0.0289(11) 0.0312(13) 0.0309(11) 0.0033(9) 0.0043(9) 0.0052(10) C13 0.0233(9) 0.0242(11) 0.0196(9) -0.0011(8) 0.0055(7) -0.0012(9) C14 0.0294(10) 0.0207(11) 0.0269(10) -0.0051(8) 0.0061(8) 0.0002(9) C15 0.0360(12) 0.0251(12) 0.0324(12) -0.0081(9) 0.0084(9) -0.0077(10) C16 0.0279(11) 0.0374(14) 0.0354(12) -0.0115(10) 0.0044(9) -0.0108(10) C17 0.0228(10) 0.0355(14) 0.0324(12) -0.0042(10) 0.0026(8) -0.0041(10) C18 0.0276(12) 0.0485(17) 0.0544(16) -0.0031(13) -0.0027(11) -0.0002(12) C19 0.0247(10) 0.0242(11) 0.0181(9) 0.0014(8) 0.0006(7) 0.0007(9) C20 0.0294(10) 0.0228(12) 0.0253(11) 0.0003(8) 0.0003(8) -0.0009(9) C21 0.0262(10) 0.0345(14) 0.0327(12) -0.0042(10) 0.0055(9) 0.0063(10) C22 0.0238(10) 0.0412(14) 0.0252(11) 0.0026(9) 0.0039(8) -0.0039(10) C23 0.0303(11) 0.0277(12) 0.0259(11) 0.0035(9) 0.0000(8) -0.0046(10) C24 0.0271(10) 0.0246(11) 0.0223(10) 0.0009(8) 0.0004(8) 0.0043(9) C25 0.0206(9) 0.0194(10) 0.0223(10) 0.0025(8) 0.0020(7) -0.0022(8) C26 0.0216(9) 0.0217(11) 0.0266(10) 0.0000(8) 0.0027(8) 0.0006(9) C27 0.0267(10) 0.0294(12) 0.0234(10) 0.0036(9) -0.0025(8) -0.0025(9) C28 0.0347(11) 0.0335(13) 0.0205(10) -0.0058(9) 0.0033(8) -0.0055(10) C29 0.0321(11) 0.0277(13) 0.0347(12) -0.0064(10) 0.0071(9) 0.0036(10) C30 0.0245(10) 0.0250(12) 0.0273(11) 0.0020(9) -0.0013(8) 0.0033(9) C31 0.0214(9) 0.0224(11) 0.0188(9) -0.0019(8) -0.0047(7) 0.0003(8) C32 0.0271(10) 0.0222(11) 0.0236(10) -0.0026(8) -0.0023(8) 0.0011(9) C33 0.0321(11) 0.0231(12) 0.0254(10) -0.0002(8) -0.0023(8) -0.0053(9) C34 0.0245(10) 0.0316(13) 0.0293(11) 0.0003(9) -0.0011(8) -0.0063(9) C35 0.0197(9) 0.0318(13) 0.0294(11) -0.0006(9) -0.0027(8) -0.0014(9) C36 0.0269(11) 0.0392(15) 0.0488(15) 0.0022(12) 0.0028(10) 0.0046(11) _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 N1 1.534(3) . ? B1 C1 1.627(3) . ? B1 C7 1.643(3) . ? B1 Cl1 1.929(2) . ? B2 N3 1.542(3) . ? B2 C19 1.624(3) . ? B2 C25 1.640(3) . ? B2 Cl2 1.917(2) . ? N1 C13 1.325(3) . ? N1 H1 0.82(2) . ? N2 C13 1.355(3) . ? N2 C17 1.373(3) . ? N2 H2 0.86(3) . ? N3 C31 1.320(3) . ? N3 H3 0.83(2) . ? N4 C31 1.354(3) . ? N4 C35 1.374(3) . ? N4 H4 0.82(2) . ? F2 C2 1.358(2) . ? F3 C3 1.336(2) . ? F4 C4 1.341(2) . ? F5 C5 1.339(2) . ? F6 C6 1.350(2) . ? F8 C8 1.346(2) . ? F9 C9 1.341(3) . ? F10 C10 1.339(3) . ? F11 C11 1.343(3) . ? F12 C12 1.352(2) . ? F13 C18 1.317(3) . ? F14 C18 1.286(3) . ? F15 C18 1.308(3) . ? F20 C20 1.354(2) . ? F21 C21 1.342(2) . ? F22 C22 1.341(2) . ? F23 C23 1.341(3) . ? F24 C24 1.344(2) . ? F26 C26 1.346(2) . ? F27 C27 1.338(2) . ? F28 C28 1.343(2) . ? F29 C29 1.342(3) . ? F30 C30 1.355(2) . ? F31 C36 1.316(3) . ? F32 C36 1.299(3) . ? F33 C36 1.334(3) . ? C1 C2 1.381(3) . ? C1 C6 1.390(3) . ? C2 C3 1.380(3) . ? C3 C4 1.368(3) . ? C4 C5 1.378(3) . ? C5 C6 1.377(3) . ? C7 C8 1.386(3) . ? C7 C12 1.389(3) . ? C8 C9 1.380(3) . ? C9 C10 1.364(3) . ? C10 C11 1.372(4) . ? C11 C12 1.374(3) . ? C13 C14 1.417(3) . ? C14 C15 1.354(3) . ? C14 H14A 0.9500 . ? C15 C16 1.410(3) . ? C15 H15A 0.9500 . ? C16 C17 1.345(3) . ? C16 H16A 0.9500 . ? C17 C18 1.498(3) . ? C19 C20 1.382(3) . ? C19 C24 1.390(3) . ? C20 C21 1.378(3) . ? C21 C22 1.370(3) . ? C22 C23 1.368(3) . ? C23 C24 1.380(3) . ? C25 C30 1.382(3) . ? C25 C26 1.393(3) . ? C26 C27 1.376(3) . ? C27 C28 1.368(3) . ? C28 C29 1.373(3) . ? C29 C30 1.383(3) . ? C31 C32 1.417(3) . ? C32 C33 1.356(3) . ? C32 H32A 0.9500 . ? C33 C34 1.415(3) . ? C33 H33A 0.9500 . ? C34 C35 1.343(3) . ? C34 H34A 0.9500 . ? C35 C36 1.492(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 N1 B1 C1 113.81(17) . . ? N1 B1 C7 108.25(16) . . ? C1 B1 C7 110.47(16) . . ? N1 B1 Cl1 105.45(14) . . ? C1 B1 Cl1 106.07(14) . . ? C7 B1 Cl1 112.77(14) . . ? N3 B2 C19 114.31(17) . . ? N3 B2 C25 107.37(16) . . ? C19 B2 C25 108.88(16) . . ? N3 B2 Cl2 105.46(14) . . ? C19 B2 Cl2 106.60(14) . . ? C25 B2 Cl2 114.37(14) . . ? C13 N1 B1 125.82(18) . . ? C13 N1 H1 112.0(16) . . ? B1 N1 H1 121.8(16) . . ? C13 N2 C17 123.1(2) . . ? C13 N2 H2 117.9(16) . . ? C17 N2 H2 118.5(16) . . ? C31 N3 B2 124.96(18) . . ? C31 N3 H3 116.7(17) . . ? B2 N3 H3 118.1(17) . . ? C31 N4 C35 123.22(19) . . ? C31 N4 H4 116.1(16) . . ? C35 N4 H4 120.0(16) . . ? C2 C1 C6 113.72(18) . . ? C2 C1 B1 127.50(18) . . ? C6 C1 B1 118.75(18) . . ? F2 C2 C3 115.21(17) . . ? F2 C2 C1 120.58(17) . . ? C3 C2 C1 124.19(19) . . ? F3 C3 C4 119.16(18) . . ? F3 C3 C2 121.48(19) . . ? C4 C3 C2 119.36(19) . . ? F4 C4 C3 119.95(19) . . ? F4 C4 C5 120.57(19) . . ? C3 C4 C5 119.47(19) . . ? F5 C5 C6 120.89(19) . . ? F5 C5 C4 120.07(18) . . ? C6 C5 C4 119.03(19) . . ? F6 C6 C5 115.99(19) . . ? F6 C6 C1 119.85(18) . . ? C5 C6 C1 124.16(19) . . ? C8 C7 C12 113.61(19) . . ? C8 C7 B1 129.95(18) . . ? C12 C7 B1 116.43(18) . . ? F8 C8 C9 115.34(19) . . ? F8 C8 C7 120.94(18) . . ? C9 C8 C7 123.7(2) . . ? F9 C9 C10 119.6(2) . . ? F9 C9 C8 120.5(2) . . ? C10 C9 C8 119.8(2) . . ? F10 C10 C9 120.0(2) . . ? F10 C10 C11 120.7(2) . . ? C9 C10 C11 119.3(2) . . ? F11 C11 C10 120.0(2) . . ? F11 C11 C12 120.7(2) . . ? C10 C11 C12 119.3(2) . . ? F12 C12 C11 116.65(19) . . ? F12 C12 C7 119.10(19) . . ? C11 C12 C7 124.3(2) . . ? N1 C13 N2 119.62(19) . . ? N1 C13 C14 123.78(19) . . ? N2 C13 C14 116.60(18) . . ? C15 C14 C13 120.3(2) . . ? C15 C14 H14A 119.8 . . ? C13 C14 H14A 119.8 . . ? C14 C15 C16 121.2(2) . . ? C14 C15 H15A 119.4 . . ? C16 C15 H15A 119.4 . . ? C17 C16 C15 118.0(2) . . ? C17 C16 H16A 121.0 . . ? C15 C16 H16A 121.0 . . ? C16 C17 N2 120.6(2) . . ? C16 C17 C18 124.7(2) . . ? N2 C17 C18 114.7(2) . . ? F14 C18 F15 108.4(3) . . ? F14 C18 F13 107.7(2) . . ? F15 C18 F13 104.6(2) . . ? F14 C18 C17 112.5(2) . . ? F15 C18 C17 111.9(2) . . ? F13 C18 C17 111.5(2) . . ? C20 C19 C24 113.82(18) . . ? C20 C19 B2 127.75(19) . . ? C24 C19 B2 118.41(18) . . ? F20 C20 C21 115.76(19) . . ? F20 C20 C19 120.39(18) . . ? C21 C20 C19 123.8(2) . . ? F21 C21 C22 119.65(19) . . ? F21 C21 C20 120.6(2) . . ? C22 C21 C20 119.8(2) . . ? F22 C22 C23 120.4(2) . . ? F22 C22 C21 120.5(2) . . ? C23 C22 C21 119.15(19) . . ? F23 C23 C22 120.22(19) . . ? F23 C23 C24 120.3(2) . . ? C22 C23 C24 119.4(2) . . ? F24 C24 C23 116.32(19) . . ? F24 C24 C19 119.75(18) . . ? C23 C24 C19 123.9(2) . . ? C30 C25 C26 113.50(18) . . ? C30 C25 B2 130.92(17) . . ? C26 C25 B2 115.57(17) . . ? F26 C26 C27 116.41(18) . . ? F26 C26 C25 119.15(17) . . ? C27 C26 C25 124.44(19) . . ? F27 C27 C28 120.57(18) . . ? F27 C27 C26 120.16(19) . . ? C28 C27 C26 119.25(19) . . ? F28 C28 C27 120.01(19) . . ? F28 C28 C29 120.7(2) . . ? C27 C28 C29 119.25(19) . . ? F29 C29 C28 119.55(19) . . ? F29 C29 C30 120.8(2) . . ? C28 C29 C30 119.7(2) . . ? F30 C30 C25 120.74(18) . . ? F30 C30 C29 115.35(18) . . ? C25 C30 C29 123.88(19) . . ? N3 C31 N4 119.00(19) . . ? N3 C31 C32 124.45(19) . . ? N4 C31 C32 116.54(18) . . ? C33 C32 C31 120.4(2) . . ? C33 C32 H32A 119.8 . . ? C31 C32 H32A 119.8 . . ? C32 C33 C34 121.1(2) . . ? C32 C33 H33A 119.5 . . ? C34 C33 H33A 119.5 . . ? C35 C34 C33 117.9(2) . . ? C35 C34 H34A 121.1 . . ? C33 C34 H34A 121.1 . . ? C34 C35 N4 120.8(2) . . ? C34 C35 C36 124.4(2) . . ? N4 C35 C36 114.8(2) . . ? F32 C36 F31 110.2(2) . . ? F32 C36 F33 106.3(2) . . ? F31 C36 F33 104.2(2) . . ? F32 C36 C35 112.0(2) . . ? F31 C36 C35 112.09(19) . . ? F33 C36 C35 111.6(2) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.680 _refine_diff_density_min -0.535 _refine_diff_density_rms 0.057 # Attachment '- 12-SJG91_0m.cif' data_sjg91_0m _database_code_depnum_ccdc_archive 'CCDC 846350' #TrackingRef '- 12-SJG91_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H8 B Cl F10 N2' _chemical_formula_weight 524.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 9.9317(4) _cell_length_b 17.7746(8) _cell_length_c 11.3370(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.843(2) _cell_angle_gamma 90.00 _cell_volume 1982.62(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4556 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.757 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6600 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16792 _diffrn_reflns_av_R_equivalents 0.0700 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 27.54 _reflns_number_total 4556 _reflns_number_gt 3584 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0507P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4556 _refine_ls_number_parameters 324 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0934 _refine_ls_wR_factor_gt 0.0884 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _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 -0.34357(16) -0.03428(9) 0.86436(17) 0.0175(4) Uani 1 1 d . . . N1 N -0.43763(12) 0.03287(7) 0.88140(12) 0.0189(3) Uani 1 1 d . . . N2 N -0.26987(12) 0.11862(7) 0.95112(12) 0.0192(3) Uani 1 1 d . . . Cl1 Cl -0.24180(3) -0.05380(2) 1.01633(4) 0.02176(11) Uani 1 1 d . . . F2 F -0.65047(8) -0.06122(5) 0.79458(9) 0.0266(2) Uani 1 1 d . . . F3 F -0.76196(9) -0.19305(6) 0.73275(10) 0.0382(3) Uani 1 1 d . . . F4 F -0.60590(11) -0.31880(6) 0.72837(11) 0.0450(3) Uani 1 1 d . . . F5 F -0.33012(10) -0.30752(5) 0.78268(10) 0.0364(3) Uani 1 1 d . . . F6 F -0.21492(8) -0.17490(5) 0.83457(9) 0.0288(2) Uani 1 1 d . . . F8 F -0.45047(8) 0.01735(5) 0.63740(8) 0.0261(2) Uani 1 1 d . . . F9 F -0.31985(9) 0.07887(6) 0.47049(9) 0.0330(3) Uani 1 1 d . . . F10 F -0.04402(9) 0.08430(6) 0.50066(9) 0.0331(3) Uani 1 1 d . . . F11 F 0.09917(8) 0.02258(6) 0.69797(10) 0.0329(3) Uani 1 1 d . . . F12 F -0.02677(8) -0.03558(6) 0.86821(9) 0.0314(3) Uani 1 1 d . . . C1 C -0.42584(14) -0.11097(8) 0.82213(14) 0.0181(3) Uani 1 1 d . . . C2 C -0.56482(14) -0.12037(9) 0.79299(14) 0.0206(3) Uani 1 1 d . . . C3 C -0.62663(15) -0.18852(10) 0.76054(16) 0.0261(4) Uani 1 1 d . . . C4 C -0.54774(17) -0.25196(9) 0.75815(17) 0.0291(4) Uani 1 1 d . . . C5 C -0.40939(17) -0.24590(9) 0.78508(16) 0.0261(4) Uani 1 1 d . . . C6 C -0.35234(15) -0.17687(9) 0.81392(15) 0.0210(3) Uani 1 1 d . . . C7 C -0.24663(14) -0.00907(8) 0.76429(14) 0.0175(3) Uani 1 1 d . . . C8 C -0.31287(14) 0.01886(8) 0.65762(15) 0.0190(3) Uani 1 1 d . . . C9 C -0.24849(15) 0.04940(9) 0.56847(15) 0.0222(3) Uani 1 1 d . . . C10 C -0.10921(15) 0.05166(9) 0.58387(16) 0.0231(4) Uani 1 1 d . . . C11 C -0.03705(14) 0.02194(9) 0.68454(16) 0.0228(4) Uani 1 1 d . . . C12 C -0.10551(14) -0.00795(9) 0.77207(15) 0.0208(3) Uani 1 1 d . . . C13 C -0.39951(14) 0.10323(8) 0.90681(14) 0.0182(3) Uani 1 1 d . . . C14 C -0.49218(14) 0.16547(9) 0.88753(15) 0.0221(4) Uani 1 1 d . . . H14A H -0.5854 0.1566 0.8597 0.027 Uiso 1 1 calc R . . C15 C -0.44746(15) 0.23648(9) 0.90868(16) 0.0245(4) Uani 1 1 d . . . H15A H -0.5097 0.2771 0.8942 0.029 Uiso 1 1 calc R . . C16 C -0.30866(14) 0.25180(9) 0.95228(15) 0.0216(3) Uani 1 1 d . . . C17 C -0.25637(16) 0.32512(9) 0.97342(17) 0.0291(4) Uani 1 1 d . . . H17A H -0.3150 0.3673 0.9588 0.035 Uiso 1 1 calc R . . C18 C -0.12218(17) 0.33591(10) 1.01474(18) 0.0332(4) Uani 1 1 d . . . H18A H -0.0878 0.3855 1.0287 0.040 Uiso 1 1 calc R . . C19 C -0.03490(16) 0.27400(10) 1.03657(18) 0.0315(4) Uani 1 1 d . . . H19A H 0.0582 0.2822 1.0659 0.038 Uiso 1 1 calc R . . C20 C -0.08161(15) 0.20164(9) 1.01627(16) 0.0255(4) Uani 1 1 d . . . H20A H -0.0217 0.1600 1.0306 0.031 Uiso 1 1 calc R . . C21 C -0.21889(14) 0.19088(8) 0.97411(15) 0.0193(3) Uani 1 1 d . . . H1 H -0.5264(16) 0.0279(10) 0.8590(15) 0.021(4) Uiso 1 1 d . . . H2 H -0.2108(19) 0.0811(12) 0.9728(18) 0.040(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0155(7) 0.0153(8) 0.0209(10) 0.0002(7) 0.0000(6) -0.0007(6) N1 0.0147(6) 0.0166(6) 0.0250(8) 0.0008(5) 0.0013(5) -0.0012(5) N2 0.0179(6) 0.0142(6) 0.0246(8) 0.0012(6) 0.0003(5) 0.0005(5) Cl1 0.02098(18) 0.0213(2) 0.0216(2) 0.00190(16) -0.00213(14) -0.00121(14) F2 0.0165(4) 0.0269(5) 0.0355(6) -0.0049(4) -0.0002(4) 0.0014(3) F3 0.0239(5) 0.0427(7) 0.0463(7) -0.0074(5) -0.0014(4) -0.0148(4) F4 0.0532(7) 0.0232(5) 0.0576(8) -0.0089(5) 0.0037(6) -0.0192(5) F5 0.0498(6) 0.0154(5) 0.0436(7) 0.0003(5) 0.0050(5) 0.0052(4) F6 0.0215(5) 0.0227(5) 0.0405(7) -0.0014(4) -0.0016(4) 0.0040(4) F8 0.0159(4) 0.0338(5) 0.0274(6) 0.0063(4) -0.0012(4) 0.0010(4) F9 0.0323(5) 0.0414(6) 0.0248(6) 0.0123(5) 0.0027(4) 0.0036(4) F10 0.0345(5) 0.0338(6) 0.0350(7) 0.0036(5) 0.0186(5) -0.0045(4) F11 0.0154(4) 0.0401(6) 0.0441(7) -0.0028(5) 0.0073(4) -0.0035(4) F12 0.0173(4) 0.0415(6) 0.0333(6) 0.0087(5) -0.0042(4) 0.0016(4) C1 0.0216(7) 0.0162(7) 0.0163(8) 0.0020(6) 0.0014(6) -0.0025(6) C2 0.0211(7) 0.0213(8) 0.0193(9) 0.0000(7) 0.0031(6) -0.0004(6) C3 0.0215(8) 0.0309(9) 0.0256(10) -0.0014(7) 0.0015(6) -0.0105(6) C4 0.0386(9) 0.0188(8) 0.0294(11) -0.0015(7) 0.0027(7) -0.0135(7) C5 0.0366(9) 0.0153(8) 0.0264(10) 0.0021(7) 0.0043(7) 0.0009(6) C6 0.0202(7) 0.0197(8) 0.0225(9) 0.0019(7) 0.0002(6) -0.0008(6) C7 0.0178(7) 0.0133(7) 0.0211(9) -0.0020(6) 0.0012(6) -0.0007(5) C8 0.0149(7) 0.0166(7) 0.0254(9) -0.0002(6) 0.0025(6) 0.0009(5) C9 0.0261(8) 0.0199(8) 0.0200(9) 0.0018(7) 0.0012(6) 0.0017(6) C10 0.0261(8) 0.0174(8) 0.0284(10) -0.0010(7) 0.0130(7) -0.0020(6) C11 0.0154(7) 0.0202(8) 0.0336(10) -0.0051(7) 0.0054(6) -0.0012(6) C12 0.0196(7) 0.0176(7) 0.0243(9) -0.0009(7) -0.0007(6) 0.0006(6) C13 0.0183(7) 0.0179(7) 0.0188(9) 0.0016(6) 0.0040(6) -0.0010(6) C14 0.0156(7) 0.0204(8) 0.0302(10) 0.0010(7) 0.0023(6) 0.0009(6) C15 0.0197(7) 0.0195(8) 0.0340(11) 0.0017(7) 0.0030(7) 0.0037(6) C16 0.0194(7) 0.0186(8) 0.0270(10) 0.0004(7) 0.0039(6) -0.0009(6) C17 0.0276(8) 0.0168(8) 0.0426(12) 0.0000(8) 0.0044(7) 0.0017(6) C18 0.0316(9) 0.0179(8) 0.0482(13) -0.0023(8) -0.0012(8) -0.0065(7) C19 0.0223(8) 0.0261(9) 0.0430(12) 0.0004(8) -0.0065(7) -0.0051(7) C20 0.0223(7) 0.0206(8) 0.0318(10) 0.0029(7) -0.0024(7) 0.0005(6) C21 0.0209(7) 0.0156(7) 0.0211(9) 0.0001(6) 0.0022(6) -0.0016(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 B1 N1 1.544(2) . ? B1 C1 1.627(2) . ? B1 C7 1.647(2) . ? B1 Cl1 1.9067(18) . ? N1 C13 1.3269(19) . ? N1 H1 0.888(16) . ? N2 C13 1.3447(18) . ? N2 C21 1.3922(19) . ? N2 H2 0.90(2) . ? F2 C2 1.3541(18) . ? F3 C3 1.3403(17) . ? F4 C4 1.3438(18) . ? F5 C5 1.3513(18) . ? F6 C6 1.3533(16) . ? F8 C8 1.3547(15) . ? F9 C9 1.3400(18) . ? F10 C10 1.3463(18) . ? F11 C11 1.3407(16) . ? F12 C12 1.3447(18) . ? C1 C2 1.3849(19) . ? C1 C6 1.390(2) . ? C2 C3 1.385(2) . ? C3 C4 1.375(2) . ? C4 C5 1.371(2) . ? C5 C6 1.372(2) . ? C7 C8 1.387(2) . ? C7 C12 1.3924(19) . ? C8 C9 1.379(2) . ? C9 C10 1.371(2) . ? C10 C11 1.368(2) . ? C11 C12 1.383(2) . ? C13 C14 1.436(2) . ? C14 C15 1.349(2) . ? C14 H14A 0.9500 . ? C15 C16 1.426(2) . ? C15 H15A 0.9500 . ? C16 C21 1.403(2) . ? C16 C17 1.411(2) . ? C17 C18 1.365(2) . ? C17 H17A 0.9500 . ? C18 C19 1.402(2) . ? C18 H18A 0.9500 . ? C19 C20 1.376(2) . ? C19 H19A 0.9500 . ? C20 C21 1.395(2) . ? C20 H20A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 B1 C1 113.34(12) . . ? N1 B1 C7 107.25(12) . . ? C1 B1 C7 110.03(13) . . ? N1 B1 Cl1 106.43(11) . . ? C1 B1 Cl1 107.24(11) . . ? C7 B1 Cl1 112.60(10) . . ? C13 N1 B1 126.60(12) . . ? C13 N1 H1 113.5(11) . . ? B1 N1 H1 118.8(11) . . ? C13 N2 C21 124.25(13) . . ? C13 N2 H2 120.5(13) . . ? C21 N2 H2 115.2(13) . . ? C2 C1 C6 113.44(13) . . ? C2 C1 B1 127.98(13) . . ? C6 C1 B1 118.58(12) . . ? F2 C2 C1 120.70(13) . . ? F2 C2 C3 115.22(13) . . ? C1 C2 C3 124.07(14) . . ? F3 C3 C4 120.12(14) . . ? F3 C3 C2 120.59(15) . . ? C4 C3 C2 119.29(14) . . ? F4 C4 C5 120.59(15) . . ? F4 C4 C3 120.22(15) . . ? C5 C4 C3 119.19(14) . . ? F5 C5 C4 120.06(14) . . ? F5 C5 C6 120.45(14) . . ? C4 C5 C6 119.49(15) . . ? F6 C6 C5 115.99(13) . . ? F6 C6 C1 119.54(13) . . ? C5 C6 C1 124.47(14) . . ? C8 C7 C12 113.80(14) . . ? C8 C7 B1 116.46(12) . . ? C12 C7 B1 129.66(14) . . ? F8 C8 C9 116.21(14) . . ? F8 C8 C7 119.20(13) . . ? C9 C8 C7 124.59(13) . . ? F9 C9 C10 120.29(14) . . ? F9 C9 C8 121.05(13) . . ? C10 C9 C8 118.62(15) . . ? F10 C10 C11 120.24(14) . . ? F10 C10 C9 119.79(15) . . ? C11 C10 C9 119.96(15) . . ? F11 C11 C10 119.81(14) . . ? F11 C11 C12 120.59(15) . . ? C10 C11 C12 119.60(14) . . ? F12 C12 C11 115.68(13) . . ? F12 C12 C7 121.01(14) . . ? C11 C12 C7 123.30(15) . . ? N1 C13 N2 120.20(13) . . ? N1 C13 C14 122.34(13) . . ? N2 C13 C14 117.46(14) . . ? C15 C14 C13 120.33(14) . . ? C15 C14 H14A 119.8 . . ? C13 C14 H14A 119.8 . . ? C14 C15 C16 121.32(14) . . ? C14 C15 H15A 119.3 . . ? C16 C15 H15A 119.3 . . ? C21 C16 C17 118.20(14) . . ? C21 C16 C15 118.34(14) . . ? C17 C16 C15 123.46(14) . . ? C18 C17 C16 120.51(15) . . ? C18 C17 H17A 119.7 . . ? C16 C17 H17A 119.7 . . ? C17 C18 C19 120.11(16) . . ? C17 C18 H18A 119.9 . . ? C19 C18 H18A 119.9 . . ? C20 C19 C18 121.20(15) . . ? C20 C19 H19A 119.4 . . ? C18 C19 H19A 119.4 . . ? C19 C20 C21 118.48(14) . . ? C19 C20 H20A 120.8 . . ? C21 C20 H20A 120.8 . . ? N2 C21 C20 120.27(13) . . ? N2 C21 C16 118.23(13) . . ? C20 C21 C16 121.50(14) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.349 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.056 # Attachment '- 16-SJG84_0m.cif' data_sjg84_0m _database_code_depnum_ccdc_archive 'CCDC 846351' #TrackingRef '- 16-SJG84_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H9 B F10 N2' _chemical_formula_weight 454.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 8.4351(16) _cell_length_b 10.3150(19) _cell_length_c 10.496(2) _cell_angle_alpha 100.424(9) _cell_angle_beta 91.554(9) _cell_angle_gamma 109.413(8) _cell_volume 843.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7306 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 35.0 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.788 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.183 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6884 _exptl_absorpt_correction_T_max 0.7469 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26080 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 35.05 _reflns_number_total 7306 _reflns_number_gt 5014 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0616P)^2^+0.0270P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7306 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0659 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1210 _refine_ls_wR_factor_gt 0.1085 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 F4 F 0.42262(9) -0.06915(6) 0.22117(7) 0.03020(16) Uani 1 1 d . . . F10 F 0.97464(9) 0.30528(7) 1.04180(7) 0.03312(17) Uani 1 1 d . . . F8 F 0.54837(8) 0.45051(7) 0.88794(6) 0.02757(15) Uani 1 1 d . . . F11 F 1.09205(8) 0.28951(7) 0.80324(8) 0.03273(16) Uani 1 1 d . . . F12 F 0.93971(8) 0.35319(6) 0.60794(6) 0.02355(14) Uani 1 1 d . . . F5 F 0.69639(8) 0.14722(6) 0.18714(6) 0.02625(14) Uani 1 1 d . . . F6 F 0.80361(8) 0.38614(6) 0.36258(6) 0.02413(14) Uani 1 1 d . . . F3 F 0.25617(8) -0.04286(6) 0.43811(7) 0.02801(15) Uani 1 1 d . . . F2 F 0.35939(8) 0.19601(6) 0.61519(6) 0.02629(15) Uani 1 1 d . . . F9 F 0.70480(9) 0.39219(7) 1.08341(6) 0.03069(16) Uani 1 1 d . . . N2 N 0.76914(11) 0.57415(8) 0.57937(8) 0.01808(16) Uani 1 1 d . . . N1 N 0.74133(10) 0.71844(8) 0.76626(8) 0.01687(15) Uani 1 1 d . . . C4 C 0.47386(13) 0.05053(9) 0.31011(10) 0.02029(19) Uani 1 1 d . . . C3 C 0.38971(12) 0.06474(9) 0.41937(10) 0.02003(19) Uani 1 1 d . . . C2 C 0.44609(12) 0.18998(9) 0.50954(9) 0.01776(18) Uani 1 1 d . . . C1 C 0.58529(11) 0.30499(9) 0.49753(9) 0.01608(17) Uani 1 1 d . . . B1 B 0.64375(13) 0.44086(10) 0.61647(10) 0.01643(19) Uani 1 1 d . . . C7 C 0.73489(11) 0.40229(9) 0.73810(9) 0.01646(17) Uani 1 1 d . . . C8 C 0.68146(12) 0.40875(9) 0.86149(10) 0.01868(18) Uani 1 1 d . . . C9 C 0.75921(13) 0.37824(10) 0.96465(10) 0.0212(2) Uani 1 1 d . . . C10 C 0.89680(13) 0.33608(10) 0.94426(11) 0.0229(2) Uani 1 1 d . . . C12 C 0.87595(12) 0.36208(9) 0.72454(10) 0.01802(18) Uani 1 1 d . . . C11 C 0.95677(12) 0.32879(10) 0.82339(11) 0.0219(2) Uani 1 1 d . . . C17 C 0.78295(12) 0.84280(10) 0.85527(10) 0.01834(18) Uani 1 1 d . . . C16 C 0.90706(13) 0.95676(10) 0.83059(10) 0.02129(19) Uani 1 1 d . . . H16A H 0.9391 1.0439 0.8906 0.026 Uiso 1 1 calc R . . C15 C 0.98794(13) 0.94473(10) 0.71527(11) 0.0223(2) Uani 1 1 d . . . H15A H 1.0742 1.0245 0.6981 0.027 Uiso 1 1 calc R . . C14 C 0.94436(12) 0.82082(10) 0.62846(10) 0.02036(19) Uani 1 1 d . . . H14A H 0.9986 0.8145 0.5506 0.024 Uiso 1 1 calc R . . C18 C 0.68644(14) 0.84043(12) 0.97199(11) 0.0256(2) Uani 1 1 d . . . H18A H 0.7304 0.9323 1.0309 0.038 Uiso 1 1 calc R . . H18B H 0.6985 0.7683 1.0169 0.038 Uiso 1 1 calc R . . H18C H 0.5669 0.8191 0.9450 0.038 Uiso 1 1 calc R . . C5 C 0.61285(12) 0.16105(9) 0.29283(9) 0.01850(18) Uani 1 1 d . . . C6 C 0.66467(12) 0.28421(9) 0.38564(9) 0.01723(17) Uani 1 1 d . . . C13 C 0.81667(11) 0.70032(9) 0.65503(9) 0.01620(17) Uani 1 1 d . . . H3 H 0.8315(19) 0.5726(15) 0.5148(14) 0.034(4) Uiso 1 1 d . . . H1 H 0.5258(15) 0.4656(12) 0.6507(12) 0.016(3) Uiso 1 1 d . . . H2 H 0.6584(17) 0.6503(14) 0.7854(13) 0.027(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F4 0.0364(4) 0.0142(3) 0.0308(4) -0.0068(2) -0.0052(3) 0.0032(2) F10 0.0357(4) 0.0307(3) 0.0327(4) 0.0118(3) -0.0090(3) 0.0091(3) F8 0.0306(3) 0.0372(3) 0.0220(3) 0.0063(3) 0.0108(2) 0.0201(3) F11 0.0229(3) 0.0295(3) 0.0490(5) 0.0066(3) 0.0012(3) 0.0139(3) F12 0.0216(3) 0.0239(3) 0.0236(3) 0.0011(2) 0.0087(2) 0.0071(2) F5 0.0328(3) 0.0234(3) 0.0197(3) -0.0022(2) 0.0058(2) 0.0091(3) F6 0.0245(3) 0.0176(3) 0.0224(3) 0.0004(2) 0.0075(2) -0.0015(2) F3 0.0233(3) 0.0161(3) 0.0371(4) 0.0070(2) 0.0001(3) -0.0038(2) F2 0.0248(3) 0.0244(3) 0.0248(3) 0.0050(2) 0.0095(2) 0.0015(2) F9 0.0418(4) 0.0335(3) 0.0156(3) 0.0063(3) 0.0053(3) 0.0104(3) N2 0.0222(4) 0.0127(3) 0.0169(4) 0.0008(3) 0.0045(3) 0.0038(3) N1 0.0175(4) 0.0129(3) 0.0177(4) 0.0007(3) 0.0015(3) 0.0033(3) C4 0.0243(5) 0.0109(3) 0.0216(5) -0.0015(3) -0.0047(4) 0.0037(3) C3 0.0177(4) 0.0126(4) 0.0261(5) 0.0048(3) -0.0021(3) 0.0002(3) C2 0.0177(4) 0.0156(4) 0.0180(4) 0.0036(3) 0.0019(3) 0.0031(3) C1 0.0168(4) 0.0130(3) 0.0165(4) 0.0024(3) 0.0004(3) 0.0030(3) B1 0.0178(4) 0.0136(4) 0.0156(5) 0.0017(3) 0.0025(3) 0.0029(3) C7 0.0171(4) 0.0118(3) 0.0172(4) 0.0002(3) 0.0017(3) 0.0021(3) C8 0.0206(4) 0.0159(4) 0.0186(5) 0.0013(3) 0.0032(3) 0.0060(3) C9 0.0270(5) 0.0168(4) 0.0162(5) 0.0026(3) 0.0021(3) 0.0033(4) C10 0.0243(5) 0.0157(4) 0.0249(5) 0.0041(3) -0.0058(4) 0.0026(3) C12 0.0177(4) 0.0135(3) 0.0196(5) 0.0002(3) 0.0039(3) 0.0025(3) C11 0.0174(4) 0.0149(4) 0.0314(6) 0.0022(4) -0.0002(4) 0.0043(3) C17 0.0193(4) 0.0165(4) 0.0185(5) -0.0005(3) -0.0016(3) 0.0074(3) C16 0.0226(5) 0.0145(4) 0.0231(5) -0.0019(3) -0.0021(4) 0.0049(3) C15 0.0199(4) 0.0143(4) 0.0291(5) 0.0029(4) 0.0014(4) 0.0022(3) C14 0.0206(4) 0.0153(4) 0.0234(5) 0.0030(3) 0.0054(3) 0.0039(3) C18 0.0273(5) 0.0261(5) 0.0202(5) -0.0018(4) 0.0030(4) 0.0083(4) C5 0.0224(4) 0.0154(4) 0.0160(4) -0.0001(3) 0.0002(3) 0.0061(3) C6 0.0176(4) 0.0132(3) 0.0175(4) 0.0019(3) 0.0010(3) 0.0015(3) C13 0.0172(4) 0.0134(3) 0.0171(4) 0.0017(3) 0.0010(3) 0.0047(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 F4 C4 1.3374(11) . ? F10 C10 1.3417(13) . ? F8 C8 1.3483(12) . ? F11 C11 1.3418(12) . ? F12 C12 1.3503(11) . ? F5 C5 1.3415(12) . ? F6 C6 1.3512(10) . ? F3 C3 1.3414(11) . ? F2 C2 1.3482(12) . ? F9 C9 1.3398(12) . ? N2 C13 1.3217(12) . ? N2 B1 1.5524(13) . ? N2 H3 0.870(15) . ? N1 C13 1.3572(13) . ? N1 C17 1.3751(12) . ? N1 H2 0.869(14) . ? C4 C3 1.3759(15) . ? C4 C5 1.3802(13) . ? C3 C2 1.3840(13) . ? C2 C1 1.3921(12) . ? C1 C6 1.3858(13) . ? C1 B1 1.6248(14) . ? B1 C7 1.6471(15) . ? B1 H1 1.157(12) . ? C7 C8 1.3803(14) . ? C7 C12 1.3871(14) . ? C8 C9 1.3869(15) . ? C9 C10 1.3773(16) . ? C10 C11 1.3772(16) . ? C12 C11 1.3803(15) . ? C17 C16 1.3607(14) . ? C17 C18 1.4886(15) . ? C16 C15 1.4116(15) . ? C16 H16A 0.9500 . ? C15 C14 1.3591(13) . ? C15 H15A 0.9500 . ? C14 C13 1.4264(13) . ? C14 H14A 0.9500 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C5 C6 1.3835(13) . ? 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 N2 B1 123.72(8) . . ? C13 N2 H3 111.2(10) . . ? B1 N2 H3 124.0(9) . . ? C13 N1 C17 124.57(8) . . ? C13 N1 H2 121.1(9) . . ? C17 N1 H2 114.3(9) . . ? F4 C4 C3 120.67(9) . . ? F4 C4 C5 119.91(9) . . ? C3 C4 C5 119.42(8) . . ? F3 C3 C4 119.88(8) . . ? F3 C3 C2 120.92(9) . . ? C4 C3 C2 119.20(8) . . ? F2 C2 C3 116.10(8) . . ? F2 C2 C1 119.88(8) . . ? C3 C2 C1 124.01(9) . . ? C6 C1 C2 114.06(8) . . ? C6 C1 B1 127.60(8) . . ? C2 C1 B1 118.20(8) . . ? N2 B1 C1 113.41(8) . . ? N2 B1 C7 108.62(7) . . ? C1 B1 C7 108.42(8) . . ? N2 B1 H1 108.5(6) . . ? C1 B1 H1 109.2(6) . . ? C7 B1 H1 108.7(6) . . ? C8 C7 C12 114.08(9) . . ? C8 C7 B1 123.97(9) . . ? C12 C7 B1 121.94(8) . . ? F8 C8 C7 119.70(9) . . ? F8 C8 C9 116.12(9) . . ? C7 C8 C9 124.17(10) . . ? F9 C9 C10 119.98(9) . . ? F9 C9 C8 121.04(10) . . ? C10 C9 C8 118.96(9) . . ? F10 C10 C9 120.51(10) . . ? F10 C10 C11 119.98(10) . . ? C9 C10 C11 119.49(9) . . ? F12 C12 C11 116.82(9) . . ? F12 C12 C7 119.06(9) . . ? C11 C12 C7 124.12(9) . . ? F11 C11 C10 119.82(10) . . ? F11 C11 C12 121.02(10) . . ? C10 C11 C12 119.16(10) . . ? C16 C17 N1 118.31(9) . . ? C16 C17 C18 125.42(9) . . ? N1 C17 C18 116.27(9) . . ? C17 C16 C15 119.62(9) . . ? C17 C16 H16A 120.2 . . ? C15 C16 H16A 120.2 . . ? C14 C15 C16 121.06(9) . . ? C14 C15 H15A 119.5 . . ? C16 C15 H15A 119.5 . . ? C15 C14 C13 119.57(10) . . ? C15 C14 H14A 120.2 . . ? C13 C14 H14A 120.2 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? F5 C5 C4 119.66(8) . . ? F5 C5 C6 121.00(8) . . ? C4 C5 C6 119.34(9) . . ? F6 C6 C5 115.57(8) . . ? F6 C6 C1 120.45(8) . . ? C5 C6 C1 123.97(8) . . ? N2 C13 N1 118.82(8) . . ? N2 C13 C14 124.33(9) . . ? N1 C13 C14 116.84(8) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 35.05 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.526 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.067 # Attachment '- 10-SJG88.cif' data_sjg88_0ma _database_code_depnum_ccdc_archive 'CCDC 851947' #TrackingRef '- 10-SJG88.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H8 B Cl F10 N2' _chemical_formula_weight 488.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 24.9904(18) _cell_length_b 13.1642(11) _cell_length_c 11.2738(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.412(4) _cell_angle_gamma 90.00 _cell_volume 3707.7(5) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8539 _cell_measurement_theta_min 0.8 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.750 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1936 _exptl_absorpt_coefficient_mu 0.313 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6603 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33247 _diffrn_reflns_av_R_equivalents 0.1410 _diffrn_reflns_av_sigmaI/netI 0.1803 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 0.82 _diffrn_reflns_theta_max 27.53 _reflns_number_total 8539 _reflns_number_gt 3644 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0303P)^2^+0.7649P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8539 _refine_ls_number_parameters 595 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1876 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1254 _refine_ls_wR_factor_gt 0.0884 _refine_ls_goodness_of_fit_ref 0.945 _refine_ls_restrained_S_all 0.945 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.08279(14) 0.9916(3) 0.0382(3) 0.0200(9) Uani 1 1 d . . . H1A H 0.0904(17) 0.966(3) 0.105(4) 0.044(16) Uiso 1 1 d . . . N2 N 0.09668(14) 0.8314(3) -0.0427(3) 0.0210(9) Uani 1 1 d . . . H2A H 0.0926(17) 0.795(3) -0.111(4) 0.051(16) Uiso 1 1 d . . . N3 N 0.40913(14) 1.5016(3) 0.4069(3) 0.0246(9) Uani 1 1 d . . . H3A H 0.4010(18) 1.465(4) 0.339(4) 0.059(17) Uiso 1 1 d . . . N4 N 0.40302(14) 1.3417(3) 0.4932(3) 0.0237(9) Uani 1 1 d . . . H4A H 0.4092(16) 1.311(3) 0.552(3) 0.027(15) Uiso 1 1 d . . . B1 B 0.11980(19) 0.7772(4) 0.0678(4) 0.0192(12) Uani 1 1 d . . . B2 B 0.37877(19) 1.2772(4) 0.3932(4) 0.0204(12) Uani 1 1 d . . . F2 F 0.15497(10) 0.9227(2) 0.2742(2) 0.0421(8) Uani 1 1 d . . . F3 F 0.25427(11) 0.9779(2) 0.3215(2) 0.0580(9) Uani 1 1 d . . . F4 F 0.33468(10) 0.9220(2) 0.1761(3) 0.0584(9) Uani 1 1 d . . . F5 F 0.31116(10) 0.8128(2) -0.0238(3) 0.0616(9) Uani 1 1 d . . . F6 F 0.21114(10) 0.7509(2) -0.0702(2) 0.0421(7) Uani 1 1 d . . . F8 F 0.20292(9) 0.61985(19) 0.1380(2) 0.0354(7) Uani 1 1 d . . . F9 F 0.20017(10) 0.42544(19) 0.0756(2) 0.0432(7) Uani 1 1 d . . . F10 F 0.11400(10) 0.34690(19) -0.0431(2) 0.0421(7) Uani 1 1 d . . . F11 F 0.02989(9) 0.47046(19) -0.1029(2) 0.0326(6) Uani 1 1 d . . . F12 F 0.03152(9) 0.66524(17) -0.04464(18) 0.0247(6) Uani 1 1 d . . . F20 F 0.47452(9) 1.1393(2) 0.3602(2) 0.0400(7) Uani 1 1 d . . . F21 F 0.47571(11) 0.9407(2) 0.3999(2) 0.0509(8) Uani 1 1 d . . . F22 F 0.39211(11) 0.8489(2) 0.5056(2) 0.0511(8) Uani 1 1 d . . . F23 F 0.30745(11) 0.9613(2) 0.5743(2) 0.0510(8) Uani 1 1 d . . . F24 F 0.30271(9) 1.15875(19) 0.5261(2) 0.0360(7) Uani 1 1 d . . . F26 F 0.31946(9) 1.16553(18) 0.21592(19) 0.0309(6) Uani 1 1 d . . . F27 F 0.21518(9) 1.1794(2) 0.1626(2) 0.0416(7) Uani 1 1 d . . . F28 F 0.15366(9) 1.3205(2) 0.2701(2) 0.0427(7) Uani 1 1 d . . . F29 F 0.19899(9) 1.4512(2) 0.4300(2) 0.0417(7) Uani 1 1 d . . . F30 F 0.30288(9) 1.43965(19) 0.4849(2) 0.0326(6) Uani 1 1 d . . . C1 C 0.17798(16) 0.8261(3) 0.1034(3) 0.0223(10) Uani 1 1 d . . . C2 C 0.19236(17) 0.8873(3) 0.1988(3) 0.0258(11) Uani 1 1 d . . . C3 C 0.24386(19) 0.9187(4) 0.2256(4) 0.0340(12) Uani 1 1 d . . . C4 C 0.28427(18) 0.8929(4) 0.1517(5) 0.0372(13) Uani 1 1 d . . . C5 C 0.27197(18) 0.8370(4) 0.0519(4) 0.0350(12) Uani 1 1 d . . . C6 C 0.22050(18) 0.8069(3) 0.0292(4) 0.0296(11) Uani 1 1 d . . . C7 C 0.11946(16) 0.6551(3) 0.0434(3) 0.0189(10) Uani 1 1 d . . . C8 C 0.15960(17) 0.5874(4) 0.0754(3) 0.0245(11) Uani 1 1 d . . . C9 C 0.15905(18) 0.4858(3) 0.0470(4) 0.0266(11) Uani 1 1 d . . . C10 C 0.11542(18) 0.4457(3) -0.0124(4) 0.0268(11) Uani 1 1 d . . . C11 C 0.07335(17) 0.5085(4) -0.0431(3) 0.0231(11) Uani 1 1 d . . . C12 C 0.07529(16) 0.6089(3) -0.0137(3) 0.0195(10) Uani 1 1 d . . . C13 C 0.08239(16) 0.9276(3) -0.0568(3) 0.0191(10) Uani 1 1 d . . . C14 C 0.06480(16) 0.9695(3) -0.1666(3) 0.0215(10) Uani 1 1 d . . . H14A H 0.0636 0.9285 -0.2359 0.026 Uiso 1 1 calc R . . C15 C 0.04964(16) 1.0685(3) -0.1727(4) 0.0229(10) Uani 1 1 d . . . H15A H 0.0377 1.0961 -0.2466 0.028 Uiso 1 1 calc R . . C16 C 0.05127(15) 1.1311(3) -0.0711(4) 0.0231(10) Uani 1 1 d . . . H16A H 0.0405 1.2002 -0.0765 0.028 Uiso 1 1 calc R . . C17 C 0.06815(16) 1.0922(3) 0.0336(4) 0.0211(10) Uani 1 1 d . . . C18 C 0.07200(18) 1.1495(3) 0.1484(3) 0.0307(12) Uani 1 1 d . . . H18A H 0.0587 1.2188 0.1362 0.046 Uiso 1 1 calc R . . H18B H 0.1094 1.1518 0.1763 0.046 Uiso 1 1 calc R . . H18C H 0.0504 1.1153 0.2077 0.046 Uiso 1 1 calc R . . C19 C 0.38607(16) 1.1590(3) 0.4300(3) 0.0210(10) Uani 1 1 d . . . C20 C 0.43000(17) 1.0982(4) 0.4067(3) 0.0263(11) Uani 1 1 d . . . C21 C 0.43232(18) 0.9960(4) 0.4303(4) 0.0312(12) Uani 1 1 d . . . C22 C 0.3908(2) 0.9492(4) 0.4824(4) 0.0342(12) Uani 1 1 d . . . C23 C 0.34770(18) 1.0057(4) 0.5161(4) 0.0306(11) Uani 1 1 d . . . C24 C 0.34611(16) 1.1072(3) 0.4895(3) 0.0235(10) Uani 1 1 d . . . C25 C 0.31703(15) 1.3010(3) 0.3538(3) 0.0182(10) Uani 1 1 d . . . C26 C 0.29135(17) 1.2392(3) 0.2710(4) 0.0241(11) Uani 1 1 d . . . C27 C 0.23739(18) 1.2425(4) 0.2441(4) 0.0288(11) Uani 1 1 d . . . C28 C 0.20663(16) 1.3145(4) 0.2974(4) 0.0281(11) Uani 1 1 d . . . C29 C 0.22940(17) 1.3801(3) 0.3777(4) 0.0263(11) Uani 1 1 d . . . C30 C 0.28325(17) 1.3724(3) 0.4037(3) 0.0243(11) Uani 1 1 d . . . C31 C 0.41754(16) 1.4391(4) 0.5015(4) 0.0228(11) Uani 1 1 d . . . C32 C 0.44285(15) 1.4820(3) 0.6033(4) 0.0238(11) Uani 1 1 d . . . H32A H 0.4490 1.4418 0.6723 0.029 Uiso 1 1 calc R . . C33 C 0.45827(17) 1.5806(4) 0.6021(4) 0.0328(12) Uani 1 1 d . . . H33A H 0.4757 1.6087 0.6704 0.039 Uiso 1 1 calc R . . C34 C 0.44912(17) 1.6415(4) 0.5028(4) 0.0318(12) Uani 1 1 d . . . H34A H 0.4600 1.7106 0.5038 0.038 Uiso 1 1 calc R . . C35 C 0.42464(17) 1.6019(4) 0.4047(4) 0.0288(11) Uani 1 1 d . . . C36 C 0.41203(19) 1.6575(4) 0.2916(4) 0.0431(14) Uani 1 1 d . . . H36A H 0.4249 1.7276 0.2983 0.065 Uiso 1 1 calc R . . H36B H 0.3732 1.6576 0.2768 0.065 Uiso 1 1 calc R . . H36C H 0.4297 1.6235 0.2258 0.065 Uiso 1 1 calc R . . Cl1 Cl 0.06954(4) 0.79371(8) 0.19542(8) 0.0223(3) Uani 1 1 d . . . Cl2 Cl 0.41869(4) 1.30916(9) 0.24943(8) 0.0280(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.021(2) 0.019(2) 0.020(2) -0.0009(19) -0.0007(17) 0.0003(17) N2 0.030(2) 0.016(2) 0.017(2) -0.0022(18) 0.0028(16) 0.0020(18) N3 0.028(2) 0.023(2) 0.023(2) -0.003(2) 0.0037(17) -0.0028(18) N4 0.028(2) 0.022(3) 0.021(2) 0.001(2) -0.0027(18) -0.0006(19) B1 0.028(3) 0.015(3) 0.015(2) 0.001(2) 0.006(2) 0.006(2) B2 0.021(3) 0.020(3) 0.020(2) -0.001(2) -0.001(2) -0.004(2) F2 0.0353(16) 0.059(2) 0.0321(14) -0.0196(14) 0.0096(13) -0.0125(14) F3 0.054(2) 0.079(3) 0.0404(16) -0.0054(17) -0.0106(14) -0.0362(18) F4 0.0210(16) 0.069(2) 0.085(2) 0.0211(18) -0.0071(15) -0.0135(15) F5 0.0328(17) 0.055(2) 0.099(2) -0.0013(18) 0.0380(16) -0.0004(16) F6 0.0445(18) 0.0375(18) 0.0453(16) -0.0117(14) 0.0234(14) -0.0061(14) F8 0.0272(16) 0.0320(17) 0.0463(16) 0.0070(13) -0.0116(13) 0.0016(13) F9 0.0357(17) 0.0276(17) 0.0663(19) 0.0106(14) -0.0005(14) 0.0130(13) F10 0.0516(19) 0.0187(17) 0.0563(17) -0.0058(14) 0.0100(14) 0.0000(13) F11 0.0354(16) 0.0314(17) 0.0312(14) -0.0038(12) 0.0035(12) -0.0095(13) F12 0.0215(14) 0.0261(15) 0.0264(13) 0.0054(11) -0.0023(10) 0.0020(12) F20 0.0199(15) 0.054(2) 0.0462(16) 0.0051(14) 0.0060(12) 0.0031(13) F21 0.0517(19) 0.050(2) 0.0507(17) -0.0101(15) -0.0006(14) 0.0341(16) F22 0.069(2) 0.0213(18) 0.0626(19) -0.0002(15) -0.0094(16) 0.0093(15) F23 0.0455(19) 0.0343(19) 0.074(2) 0.0192(16) 0.0090(15) -0.0046(15) F24 0.0273(16) 0.0358(17) 0.0454(15) 0.0112(13) 0.0142(12) 0.0080(13) F26 0.0261(15) 0.0350(17) 0.0314(13) -0.0164(12) -0.0020(11) 0.0033(13) F27 0.0288(16) 0.054(2) 0.0417(15) -0.0168(14) -0.0079(12) -0.0022(14) F28 0.0184(15) 0.057(2) 0.0518(16) -0.0065(15) -0.0055(12) 0.0033(14) F29 0.0261(15) 0.0427(19) 0.0562(17) -0.0120(14) 0.0043(13) 0.0135(14) F30 0.0277(15) 0.0328(17) 0.0372(15) -0.0132(13) 0.0001(12) 0.0021(12) C1 0.024(3) 0.019(3) 0.024(2) 0.007(2) 0.0014(19) -0.002(2) C2 0.024(3) 0.031(3) 0.022(2) 0.005(2) 0.000(2) -0.006(2) C3 0.032(3) 0.043(4) 0.026(3) 0.004(2) -0.010(2) -0.008(3) C4 0.019(3) 0.039(3) 0.054(3) 0.013(3) -0.005(2) -0.011(2) C5 0.020(3) 0.029(3) 0.056(3) 0.013(3) 0.014(2) 0.003(2) C6 0.035(3) 0.022(3) 0.033(3) 0.004(2) 0.010(2) 0.000(2) C7 0.021(3) 0.022(3) 0.014(2) 0.0020(19) 0.0061(18) 0.001(2) C8 0.020(3) 0.031(3) 0.023(2) -0.001(2) -0.002(2) 0.002(2) C9 0.026(3) 0.020(3) 0.034(3) 0.007(2) 0.004(2) 0.005(2) C10 0.039(3) 0.011(3) 0.031(3) 0.000(2) 0.013(2) -0.003(2) C11 0.022(3) 0.029(3) 0.019(2) -0.001(2) 0.0016(19) -0.004(2) C12 0.021(3) 0.023(3) 0.014(2) 0.003(2) 0.0055(18) 0.007(2) C13 0.016(2) 0.022(3) 0.020(2) 0.000(2) 0.0042(18) -0.003(2) C14 0.024(3) 0.023(3) 0.018(2) 0.002(2) -0.0044(19) 0.001(2) C15 0.023(3) 0.022(3) 0.024(2) 0.001(2) -0.0015(19) -0.001(2) C16 0.020(2) 0.020(3) 0.030(2) 0.003(2) -0.002(2) 0.002(2) C17 0.014(2) 0.017(3) 0.032(3) -0.004(2) 0.0027(19) -0.0018(19) C18 0.038(3) 0.024(3) 0.029(3) -0.007(2) -0.001(2) 0.002(2) C19 0.019(2) 0.024(3) 0.020(2) -0.006(2) -0.0038(18) -0.001(2) C20 0.023(3) 0.035(3) 0.021(2) -0.006(2) 0.000(2) 0.001(2) C21 0.030(3) 0.031(3) 0.032(3) -0.009(2) -0.006(2) 0.015(2) C22 0.049(3) 0.017(3) 0.036(3) -0.001(2) -0.012(2) 0.007(3) C23 0.028(3) 0.028(3) 0.036(3) 0.006(2) 0.001(2) -0.001(2) C24 0.021(3) 0.026(3) 0.024(2) 0.000(2) -0.001(2) 0.003(2) C25 0.021(2) 0.015(3) 0.018(2) 0.000(2) 0.0011(18) 0.001(2) C26 0.023(3) 0.022(3) 0.028(2) -0.001(2) 0.006(2) 0.005(2) C27 0.024(3) 0.039(3) 0.024(2) -0.006(2) -0.002(2) -0.004(2) C28 0.013(2) 0.038(3) 0.034(3) 0.006(2) -0.001(2) 0.003(2) C29 0.022(3) 0.028(3) 0.029(2) -0.004(2) 0.003(2) 0.007(2) C30 0.024(3) 0.024(3) 0.024(2) -0.001(2) -0.003(2) -0.004(2) C31 0.014(2) 0.029(3) 0.026(3) -0.002(2) 0.0034(19) 0.001(2) C32 0.016(2) 0.031(3) 0.025(2) -0.003(2) -0.0026(19) 0.002(2) C33 0.019(3) 0.035(3) 0.044(3) -0.014(3) 0.001(2) 0.005(2) C34 0.027(3) 0.018(3) 0.051(3) -0.008(3) 0.010(2) 0.004(2) C35 0.020(3) 0.025(3) 0.042(3) -0.003(3) 0.012(2) 0.006(2) C36 0.048(3) 0.035(3) 0.046(3) 0.013(3) 0.011(3) 0.004(3) Cl1 0.0210(6) 0.0272(7) 0.0188(5) 0.0029(5) 0.0037(4) 0.0022(5) Cl2 0.0276(6) 0.0353(8) 0.0212(5) -0.0040(5) 0.0032(5) -0.0069(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 N1 C13 1.362(5) . ? N1 C17 1.374(5) . ? N1 H1A 0.84(4) . ? N2 C13 1.324(5) . ? N2 B1 1.536(6) . ? N2 H2A 0.91(4) . ? N3 C31 1.358(5) . ? N3 C35 1.377(6) . ? N3 H3A 0.93(5) . ? N4 C31 1.335(5) . ? N4 B2 1.525(6) . ? N4 H4A 0.79(4) . ? B1 C7 1.630(6) . ? B1 C1 1.631(6) . ? B1 Cl1 1.945(4) . ? B2 C19 1.620(6) . ? B2 C25 1.626(6) . ? B2 Cl2 1.969(4) . ? F2 C2 1.361(4) . ? F3 C3 1.352(5) . ? F4 C4 1.339(5) . ? F5 C5 1.353(5) . ? F6 C6 1.357(5) . ? F8 C8 1.348(5) . ? F9 C9 1.333(5) . ? F10 C10 1.346(5) . ? F11 C11 1.360(5) . ? F12 C12 1.360(4) . ? F20 C20 1.354(5) . ? F21 C21 1.357(5) . ? F22 C22 1.346(5) . ? F23 C23 1.348(5) . ? F24 C24 1.353(4) . ? F26 C26 1.357(4) . ? F27 C27 1.348(5) . ? F28 C28 1.354(4) . ? F29 C29 1.350(4) . ? F30 C30 1.357(5) . ? C1 C2 1.384(6) . ? C1 C6 1.391(5) . ? C2 C3 1.378(6) . ? C3 C4 1.368(6) . ? C4 C5 1.372(6) . ? C5 C6 1.364(6) . ? C7 C8 1.384(6) . ? C7 C12 1.403(5) . ? C8 C9 1.374(6) . ? C9 C10 1.371(6) . ? C10 C11 1.375(6) . ? C11 C12 1.363(6) . ? C13 C14 1.415(5) . ? C14 C15 1.359(5) . ? C14 H14A 0.9500 . ? C15 C16 1.411(5) . ? C15 H15A 0.9500 . ? C16 C17 1.345(5) . ? C16 H16A 0.9500 . ? C17 C18 1.499(5) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.389(6) . ? C19 C24 1.395(5) . ? C20 C21 1.372(6) . ? C21 C22 1.353(6) . ? C22 C23 1.371(6) . ? C23 C24 1.369(6) . ? C25 C26 1.384(6) . ? C25 C30 1.391(5) . ? C26 C27 1.376(6) . ? C27 C28 1.368(6) . ? C28 C29 1.365(6) . ? C29 C30 1.374(6) . ? C31 C32 1.415(6) . ? C32 C33 1.353(6) . ? C32 H32A 0.9500 . ? C33 C34 1.392(6) . ? C33 H33A 0.9500 . ? C34 C35 1.355(6) . ? C34 H34A 0.9500 . ? C35 C36 1.496(6) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? 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 N1 C17 124.7(4) . . ? C13 N1 H1A 117(3) . . ? C17 N1 H1A 118(3) . . ? C13 N2 B1 129.6(4) . . ? C13 N2 H2A 112(3) . . ? B1 N2 H2A 118(3) . . ? C31 N3 C35 123.9(4) . . ? C31 N3 H3A 111(3) . . ? C35 N3 H3A 123(3) . . ? C31 N4 B2 133.5(4) . . ? C31 N4 H4A 113(3) . . ? B2 N4 H4A 114(3) . . ? N2 B1 C7 108.7(3) . . ? N2 B1 C1 109.3(3) . . ? C7 B1 C1 115.6(4) . . ? N2 B1 Cl1 108.1(3) . . ? C7 B1 Cl1 103.6(3) . . ? C1 B1 Cl1 111.2(3) . . ? N4 B2 C19 107.8(3) . . ? N4 B2 C25 116.9(4) . . ? C19 B2 C25 110.8(3) . . ? N4 B2 Cl2 106.8(3) . . ? C19 B2 Cl2 111.1(3) . . ? C25 B2 Cl2 103.3(3) . . ? C2 C1 C6 112.7(4) . . ? C2 C1 B1 129.3(4) . . ? C6 C1 B1 118.0(4) . . ? F2 C2 C3 114.3(4) . . ? F2 C2 C1 121.0(4) . . ? C3 C2 C1 124.6(4) . . ? F3 C3 C4 120.0(4) . . ? F3 C3 C2 120.6(4) . . ? C4 C3 C2 119.4(4) . . ? F4 C4 C3 120.6(5) . . ? F4 C4 C5 120.8(4) . . ? C3 C4 C5 118.6(4) . . ? F5 C5 C6 120.5(5) . . ? F5 C5 C4 119.5(4) . . ? C6 C5 C4 120.0(4) . . ? F6 C6 C5 117.1(4) . . ? F6 C6 C1 118.5(4) . . ? C5 C6 C1 124.4(4) . . ? C8 C7 C12 113.4(4) . . ? C8 C7 B1 126.2(4) . . ? C12 C7 B1 120.4(4) . . ? F8 C8 C9 115.7(4) . . ? F8 C8 C7 120.0(4) . . ? C9 C8 C7 124.3(4) . . ? F9 C9 C10 119.1(4) . . ? F9 C9 C8 121.4(4) . . ? C10 C9 C8 119.5(4) . . ? F10 C10 C9 120.9(4) . . ? F10 C10 C11 120.1(4) . . ? C9 C10 C11 119.0(4) . . ? F11 C11 C12 120.0(4) . . ? F11 C11 C10 120.0(4) . . ? C12 C11 C10 119.9(4) . . ? F12 C12 C11 116.3(4) . . ? F12 C12 C7 120.0(4) . . ? C11 C12 C7 123.7(4) . . ? N2 C13 N1 120.0(4) . . ? N2 C13 C14 123.7(4) . . ? N1 C13 C14 116.2(4) . . ? C15 C14 C13 119.9(4) . . ? C15 C14 H14A 120.0 . . ? C13 C14 H14A 120.0 . . ? C14 C15 C16 121.1(4) . . ? C14 C15 H15A 119.4 . . ? C16 C15 H15A 119.4 . . ? C17 C16 C15 119.5(4) . . ? C17 C16 H16A 120.3 . . ? C15 C16 H16A 120.3 . . ? C16 C17 N1 118.5(4) . . ? C16 C17 C18 125.3(4) . . ? N1 C17 C18 116.2(4) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C24 112.8(4) . . ? C20 C19 B2 126.1(4) . . ? C24 C19 B2 121.0(4) . . ? F20 C20 C21 115.8(4) . . ? F20 C20 C19 120.3(4) . . ? C21 C20 C19 123.9(4) . . ? C22 C21 F21 119.4(5) . . ? C22 C21 C20 120.1(4) . . ? F21 C21 C20 120.5(4) . . ? F22 C22 C21 121.1(4) . . ? F22 C22 C23 119.6(4) . . ? C21 C22 C23 119.3(5) . . ? F23 C23 C24 120.8(4) . . ? F23 C23 C22 120.0(4) . . ? C24 C23 C22 119.2(4) . . ? F24 C24 C23 116.2(4) . . ? F24 C24 C19 119.3(4) . . ? C23 C24 C19 124.4(4) . . ? C26 C25 C30 113.2(4) . . ? C26 C25 B2 119.5(4) . . ? C30 C25 B2 126.9(4) . . ? F26 C26 C27 115.9(4) . . ? F26 C26 C25 119.5(4) . . ? C27 C26 C25 124.5(4) . . ? F27 C27 C28 120.0(4) . . ? F27 C27 C26 121.0(4) . . ? C28 C27 C26 118.9(4) . . ? F28 C28 C29 120.2(4) . . ? F28 C28 C27 119.8(4) . . ? C29 C28 C27 120.0(4) . . ? F29 C29 C28 119.9(4) . . ? F29 C29 C30 121.1(4) . . ? C28 C29 C30 119.0(4) . . ? F30 C30 C29 115.6(4) . . ? F30 C30 C25 120.1(4) . . ? C29 C30 C25 124.3(4) . . ? N4 C31 N3 119.3(4) . . ? N4 C31 C32 123.7(4) . . ? N3 C31 C32 116.9(4) . . ? C33 C32 C31 119.8(4) . . ? C33 C32 H32A 120.1 . . ? C31 C32 H32A 120.1 . . ? C32 C33 C34 121.3(4) . . ? C32 C33 H33A 119.4 . . ? C34 C33 H33A 119.4 . . ? C35 C34 C33 119.8(5) . . ? C35 C34 H34A 120.1 . . ? C33 C34 H34A 120.1 . . ? C34 C35 N3 118.4(4) . . ? C34 C35 C36 126.1(5) . . ? N3 C35 C36 115.5(4) . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.353 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.087