# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Robin Hicks' _publ_contact_author_email rhicks@uvic.ca loop_ _publ_author_name 'Graeme Nawn' 'Simon Oakley' 'Marek Majewski' 'Robert McDonald' 'Brian Patrick' 'Robin Hicks' data_vic1006 _database_code_depnum_ccdc_archive 'CCDC 895624' #TrackingRef '- 2a.cif' _vrf_REFLT03_vic1006 ; RESPONSE: The crystal used for data collection was found to display non-merohedral twinning. Both components of the twin were indexed with the program CELL_NOW (Bruker AXS Inc., Madison, WI, 2004). The second twin component can be related to the first component by 180 deg rotation about the [1 -1 0] axis in both real and reciprocal space. Integrated intensities for the reflections from the two components were written into a SHELXL-97 HKLF 5 reflection file with the data integration program SAINT (version 7.68A), using all reflection data (exactly overlapped, partially overlapped and non-overlapped). The refined value of the twin fraction (SHELXL-97 BASF parameter) was 0.2410(4). ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H19 B F2 N4, C2 H3 N' _chemical_formula_sum 'C30 H22 B F2 N5' _chemical_formula_weight 501.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.9663(7) _cell_length_b 12.5933(8) _cell_length_c 19.2781(12) _cell_angle_alpha 76.0890(8) _cell_angle_beta 85.2516(9) _cell_angle_gamma 62.9902(7) _cell_volume 2511.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6000 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 24.34 _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9639 _exptl_absorpt_correction_T_max 0.9942 _exptl_absorpt_process_details 'TWINABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 18441 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0648 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.09 _diffrn_reflns_theta_max 25.84 _reflns_number_total 18441 _reflns_number_gt 10504 _reflns_threshold_expression I>2\s(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^)+(0.0521P)^2^+0.2409P] 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 18441 _refine_ls_number_parameters 688 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1209 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1330 _refine_ls_wR_factor_gt 0.1089 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.005 _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 F1A F 0.22212(11) 0.05686(10) 0.28371(6) 0.0560(3) Uani 1 1 d . . . F2A F 0.12825(10) 0.04610(10) 0.19081(7) 0.0560(3) Uani 1 1 d . . . N11A N 0.18383(13) 0.21151(13) 0.17538(8) 0.0342(4) Uani 1 1 d . . . N12A N 0.24121(14) 0.44047(13) 0.05673(8) 0.0375(4) Uani 1 1 d . . . N21A N 0.45112(14) 0.19109(13) 0.06028(8) 0.0375(4) Uani 1 1 d . . . H21A H 0.4441 0.2635 0.0377 0.045 Uiso 1 1 calc R . . N22A N 0.34886(13) -0.00398(13) 0.18321(8) 0.0325(4) Uani 1 1 d . . . C11A C 0.25451(16) 0.25102(16) 0.12761(9) 0.0319(4) Uani 1 1 d . . . C12A C 0.19207(16) 0.38607(16) 0.10454(9) 0.0322(4) Uani 1 1 d . . . C13A C 0.07569(17) 0.42362(16) 0.14494(9) 0.0329(4) Uani 1 1 d . . . C14A C 0.07495(17) 0.31591(16) 0.18593(9) 0.0344(4) Uani 1 1 d . . . C15A C -0.02409(18) 0.31766(18) 0.22871(10) 0.0433(5) Uani 1 1 d . . . H15A H -0.0229 0.2442 0.2572 0.052 Uiso 1 1 calc R . . C16A C -0.12547(18) 0.43077(19) 0.22845(11) 0.0467(5) Uani 1 1 d . . . H16A H -0.1956 0.4345 0.2567 0.056 Uiso 1 1 calc R . . C17A C -0.12671(18) 0.53847(18) 0.18793(10) 0.0432(5) Uani 1 1 d . . . H17A H -0.1974 0.6145 0.1888 0.052 Uiso 1 1 calc R . . C18A C -0.02623(17) 0.53633(17) 0.14636(10) 0.0376(5) Uani 1 1 d . . . H18A H -0.0266 0.6103 0.1193 0.045 Uiso 1 1 calc R . . C21A C 0.36569(16) 0.16970(16) 0.10676(9) 0.0326(4) Uani 1 1 d . . . C22A C 0.41266(16) 0.04062(16) 0.13461(9) 0.0317(4) Uani 1 1 d . . . C23A C 0.53023(16) -0.01599(16) 0.10064(9) 0.0333(4) Uani 1 1 d . . . C24A C 0.54861(17) 0.08086(17) 0.05510(10) 0.0360(4) Uani 1 1 d . . . C25A C 0.65342(18) 0.05929(19) 0.01315(10) 0.0431(5) Uani 1 1 d . . . H25A H 0.6665 0.1250 -0.0158 0.052 Uiso 1 1 calc R . . C26A C 0.73730(18) -0.0602(2) 0.01506(11) 0.0495(5) Uani 1 1 d . . . H26A H 0.8093 -0.0772 -0.0135 0.059 Uiso 1 1 calc R . . C27A C 0.71951(18) -0.15800(19) 0.05819(11) 0.0471(5) Uani 1 1 d . . . H27A H 0.7787 -0.2397 0.0576 0.057 Uiso 1 1 calc R . . C28A C 0.61786(17) -0.13749(17) 0.10128(10) 0.0405(5) Uani 1 1 d . . . H28A H 0.6070 -0.2041 0.1309 0.049 Uiso 1 1 calc R . . C31A C 0.18431(16) 0.56993(16) 0.03504(9) 0.0328(4) Uani 1 1 d . . . C32A C 0.19216(19) 0.64000(18) 0.07784(11) 0.0460(5) Uani 1 1 d . . . H32A H 0.2313 0.6016 0.1240 0.055 Uiso 1 1 calc R . . C33A C 0.14353(19) 0.76558(19) 0.05401(12) 0.0512(6) Uani 1 1 d . . . H33A H 0.1488 0.8132 0.0839 0.061 Uiso 1 1 calc R . . C34A C 0.08742(18) 0.82173(18) -0.01306(11) 0.0462(5) Uani 1 1 d . . . H34A H 0.0543 0.9080 -0.0296 0.055 Uiso 1 1 calc R . . C35A C 0.07956(19) 0.75278(18) -0.05592(11) 0.0497(5) Uani 1 1 d . . . H35A H 0.0402 0.7915 -0.1020 0.060 Uiso 1 1 calc R . . C36A C 0.12864(18) 0.62720(17) -0.03233(10) 0.0420(5) Uani 1 1 d . . . H36A H 0.1241 0.5799 -0.0627 0.050 Uiso 1 1 calc R . . C41A C 0.40519(16) -0.13375(16) 0.21644(10) 0.0331(4) Uani 1 1 d . . . C42A C 0.48984(19) -0.17951(18) 0.27278(11) 0.0481(5) Uani 1 1 d . . . H42A H 0.5127 -0.1265 0.2892 0.058 Uiso 1 1 calc R . . C43A C 0.5416(2) -0.30248(18) 0.30545(12) 0.0548(6) Uani 1 1 d . . . H43A H 0.6002 -0.3339 0.3443 0.066 Uiso 1 1 calc R . . C44A C 0.50912(19) -0.37960(18) 0.28221(12) 0.0487(5) Uani 1 1 d . . . H44A H 0.5448 -0.4642 0.3049 0.058 Uiso 1 1 calc R . . C45A C 0.4247(2) -0.33390(19) 0.22594(12) 0.0528(6) Uani 1 1 d . . . H45A H 0.4023 -0.3873 0.2096 0.063 Uiso 1 1 calc R . . C46A C 0.37178(19) -0.21041(18) 0.19282(11) 0.0463(5) Uani 1 1 d . . . H46A H 0.3129 -0.1790 0.1541 0.056 Uiso 1 1 calc R . . B1A B 0.2182(2) 0.0766(2) 0.20988(12) 0.0372(5) Uani 1 1 d . . . F1B F 0.36344(11) 0.40025(10) 0.22364(6) 0.0597(4) Uani 1 1 d . . . F2B F 0.41248(10) 0.41644(9) 0.32988(7) 0.0523(3) Uani 1 1 d . . . N11B N 0.23164(13) 0.38367(12) 0.32260(8) 0.0316(4) Uani 1 1 d . . . N12B N 0.02209(13) 0.29039(13) 0.42656(8) 0.0371(4) Uani 1 1 d . . . N21B N 0.27627(13) 0.08193(12) 0.43052(8) 0.0332(4) Uani 1 1 d . . . H21B H 0.2065 0.0838 0.4501 0.040 Uiso 1 1 calc R . . N22B N 0.44972(12) 0.21671(12) 0.31811(7) 0.0288(3) Uani 1 1 d . . . C11B C 0.20051(16) 0.29836(16) 0.36515(9) 0.0302(4) Uani 1 1 d . . . C12B C 0.06903(16) 0.35632(16) 0.38659(9) 0.0316(4) Uani 1 1 d . . . C13B C 0.02404(16) 0.48705(16) 0.35250(10) 0.0331(4) Uani 1 1 d . . . C14B C 0.12448(16) 0.49831(16) 0.31452(9) 0.0331(4) Uani 1 1 d . . . C15B C 0.11420(18) 0.61108(17) 0.27607(10) 0.0416(5) Uani 1 1 d . . . H15B H 0.1832 0.6187 0.2514 0.050 Uiso 1 1 calc R . . C16B C -0.0012(2) 0.71190(18) 0.27531(11) 0.0492(5) Uani 1 1 d . . . H16B H -0.0113 0.7901 0.2491 0.059 Uiso 1 1 calc R . . C17B C -0.10260(19) 0.70225(18) 0.31165(11) 0.0484(5) Uani 1 1 d . . . H17B H -0.1805 0.7733 0.3097 0.058 Uiso 1 1 calc R . . C18B C -0.09092(18) 0.59011(17) 0.35059(10) 0.0419(5) Uani 1 1 d . . . H18B H -0.1600 0.5833 0.3756 0.050 Uiso 1 1 calc R . . C21B C 0.28846(16) 0.17897(16) 0.38564(9) 0.0295(4) Uani 1 1 d . . . C22B C 0.41417(15) 0.13871(15) 0.36270(9) 0.0280(4) Uani 1 1 d . . . C23B C 0.48097(15) 0.01159(15) 0.39814(9) 0.0292(4) Uani 1 1 d . . . C24B C 0.39208(16) -0.01841(16) 0.43944(9) 0.0311(4) Uani 1 1 d . . . C25B C 0.42439(18) -0.13423(16) 0.48308(10) 0.0395(5) Uani 1 1 d . . . H25B H 0.3633 -0.1541 0.5096 0.047 Uiso 1 1 calc R . . C26B C 0.54847(19) -0.21869(17) 0.48616(10) 0.0424(5) Uani 1 1 d . . . H26B H 0.5732 -0.2985 0.5155 0.051 Uiso 1 1 calc R . . C27B C 0.63947(18) -0.19047(16) 0.44733(10) 0.0382(5) Uani 1 1 d . . . H27B H 0.7246 -0.2509 0.4515 0.046 Uiso 1 1 calc R . . C28B C 0.60770(16) -0.07692(16) 0.40335(9) 0.0334(4) Uani 1 1 d . . . H28B H 0.6698 -0.0584 0.3770 0.040 Uiso 1 1 calc R . . C31B C -0.09988(16) 0.34449(16) 0.45391(10) 0.0339(4) Uani 1 1 d . . . C32B C -0.19640(17) 0.33148(17) 0.42834(10) 0.0403(5) Uani 1 1 d . . . H32B H -0.1830 0.2928 0.3897 0.048 Uiso 1 1 calc R . . C33B C -0.31267(17) 0.37493(17) 0.45924(11) 0.0435(5) Uani 1 1 d . . . H33B H -0.3798 0.3685 0.4406 0.052 Uiso 1 1 calc R . . C34B C -0.33153(18) 0.42731(18) 0.51664(11) 0.0480(5) Uani 1 1 d . . . H34B H -0.4106 0.4545 0.5387 0.058 Uiso 1 1 calc R . . C35B C -0.23537(19) 0.4402(2) 0.54187(12) 0.0583(6) Uani 1 1 d . . . H35B H -0.2484 0.4772 0.5812 0.070 Uiso 1 1 calc R . . C36B C -0.11969(19) 0.3995(2) 0.51043(11) 0.0528(6) Uani 1 1 d . . . H36B H -0.0539 0.4096 0.5278 0.063 Uiso 1 1 calc R . . C41B C 0.57348(16) 0.16972(15) 0.28936(9) 0.0296(4) Uani 1 1 d . . . C42B C 0.60033(17) 0.10041(17) 0.23895(10) 0.0385(5) Uani 1 1 d . . . H42B H 0.5375 0.0839 0.2237 0.046 Uiso 1 1 calc R . . C43B C 0.71901(18) 0.05490(18) 0.21057(11) 0.0468(5) Uani 1 1 d . . . H43B H 0.7374 0.0072 0.1760 0.056 Uiso 1 1 calc R . . C44B C 0.81003(18) 0.07893(18) 0.23267(11) 0.0479(5) Uani 1 1 d . . . H44B H 0.8914 0.0480 0.2134 0.057 Uiso 1 1 calc R . . C45B C 0.78228(19) 0.14783(19) 0.28274(12) 0.0540(6) Uani 1 1 d . . . H45B H 0.8452 0.1640 0.2981 0.065 Uiso 1 1 calc R . . C46B C 0.66394(17) 0.19427(18) 0.31134(11) 0.0435(5) Uani 1 1 d . . . H46B H 0.6456 0.2424 0.3457 0.052 Uiso 1 1 calc R . . B1B B 0.3638(2) 0.35793(19) 0.29680(12) 0.0352(5) Uani 1 1 d . . . N1S N 0.4768(2) 0.3902(2) -0.05277(12) 0.0827(7) Uani 1 1 d . . . C1S C 0.4492(2) 0.4894(2) -0.07914(12) 0.0613(6) Uani 1 1 d . . . C2S C 0.4145(2) 0.6174(2) -0.11252(13) 0.0742(8) Uani 1 1 d . . . H2SA H 0.3652 0.6414 -0.1566 0.089 Uiso 1 1 calc R . . H2SB H 0.4906 0.6282 -0.1238 0.089 Uiso 1 1 calc R . . H2SC H 0.3644 0.6686 -0.0796 0.089 Uiso 1 1 calc R . . N2S N 0.1094(2) 0.0282(2) 0.54547(12) 0.0978(8) Uani 1 1 d . . . C3S C 0.0179(2) 0.0573(2) 0.57408(13) 0.0720(8) Uani 1 1 d . . . C4S C -0.1005(2) 0.0952(3) 0.61138(14) 0.0825(8) Uani 1 1 d . . . H4SA H -0.1675 0.1630 0.5793 0.099 Uiso 1 1 calc R . . H4SB H -0.0925 0.1218 0.6537 0.099 Uiso 1 1 calc R . . H4SC H -0.1209 0.0260 0.6261 0.099 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 F1A 0.0659(8) 0.0442(7) 0.0387(7) 0.0015(5) 0.0099(6) -0.0151(6) F2A 0.0379(7) 0.0394(7) 0.0895(9) -0.0029(6) -0.0026(6) -0.0213(6) N11A 0.0342(9) 0.0281(9) 0.0370(9) -0.0034(7) 0.0047(7) -0.0137(7) N12A 0.0388(9) 0.0281(9) 0.0392(9) 0.0002(7) 0.0017(7) -0.0135(8) N21A 0.0379(9) 0.0287(9) 0.0432(10) -0.0008(7) 0.0077(8) -0.0174(8) N22A 0.0340(9) 0.0256(8) 0.0357(9) 0.0013(7) -0.0030(7) -0.0148(7) C11A 0.0332(10) 0.0287(10) 0.0314(10) -0.0001(8) -0.0019(8) -0.0148(9) C12A 0.0322(10) 0.0312(11) 0.0316(10) -0.0017(8) -0.0018(8) -0.0150(9) C13A 0.0326(10) 0.0318(11) 0.0330(11) -0.0038(8) -0.0013(8) -0.0148(9) C14A 0.0331(11) 0.0330(11) 0.0344(11) -0.0030(9) 0.0007(8) -0.0148(9) C15A 0.0441(12) 0.0381(12) 0.0443(12) -0.0034(10) 0.0091(10) -0.0197(10) C16A 0.0385(12) 0.0496(14) 0.0470(13) -0.0092(11) 0.0111(10) -0.0182(11) C17A 0.0357(11) 0.0385(12) 0.0465(13) -0.0092(10) 0.0020(10) -0.0095(10) C18A 0.0357(11) 0.0321(11) 0.0395(11) -0.0026(9) -0.0039(9) -0.0124(9) C21A 0.0334(11) 0.0267(10) 0.0344(11) -0.0003(8) 0.0013(8) -0.0141(9) C22A 0.0308(10) 0.0312(11) 0.0337(10) -0.0034(8) -0.0028(8) -0.0157(9) C23A 0.0298(10) 0.0328(11) 0.0359(11) -0.0056(8) -0.0017(8) -0.0134(9) C24A 0.0318(10) 0.0348(11) 0.0388(11) -0.0054(9) -0.0002(9) -0.0141(9) C25A 0.0377(12) 0.0459(13) 0.0417(12) -0.0022(10) 0.0043(9) -0.0196(11) C26A 0.0306(11) 0.0560(15) 0.0500(13) -0.0113(11) 0.0056(10) -0.0105(11) C27A 0.0347(12) 0.0391(12) 0.0517(13) -0.0075(10) -0.0022(10) -0.0039(10) C28A 0.0350(11) 0.0328(11) 0.0445(12) -0.0030(9) -0.0035(9) -0.0095(9) C31A 0.0317(10) 0.0307(11) 0.0341(11) -0.0025(9) 0.0053(8) -0.0155(9) C32A 0.0532(13) 0.0399(13) 0.0390(12) -0.0023(10) -0.0099(10) -0.0174(11) C33A 0.0559(14) 0.0400(13) 0.0623(15) -0.0159(11) -0.0033(12) -0.0226(11) C34A 0.0418(12) 0.0279(11) 0.0616(15) -0.0008(10) 0.0001(11) -0.0137(10) C35A 0.0533(14) 0.0387(13) 0.0451(13) 0.0023(10) -0.0095(10) -0.0145(11) C36A 0.0473(12) 0.0342(12) 0.0414(12) -0.0061(9) -0.0045(10) -0.0160(10) C41A 0.0345(10) 0.0264(10) 0.0358(11) -0.0003(8) -0.0009(8) -0.0144(9) C42A 0.0560(14) 0.0353(12) 0.0529(13) -0.0012(10) -0.0196(11) -0.0211(11) C43A 0.0605(15) 0.0380(13) 0.0542(14) 0.0061(11) -0.0223(11) -0.0164(11) C44A 0.0498(13) 0.0286(11) 0.0603(14) 0.0029(10) 0.0003(11) -0.0176(10) C45A 0.0624(15) 0.0395(13) 0.0654(15) -0.0078(11) -0.0040(12) -0.0314(12) C46A 0.0531(13) 0.0390(12) 0.0497(13) 0.0008(10) -0.0128(10) -0.0262(11) B1A 0.0379(13) 0.0331(13) 0.0398(14) -0.0002(10) 0.0017(10) -0.0194(11) F1B 0.0530(7) 0.0468(7) 0.0418(7) 0.0081(6) 0.0128(6) -0.0012(6) F2B 0.0405(7) 0.0341(6) 0.0882(9) -0.0199(6) 0.0116(6) -0.0204(5) N11B 0.0288(8) 0.0245(8) 0.0352(9) -0.0029(7) 0.0003(7) -0.0084(7) N12B 0.0272(9) 0.0349(9) 0.0464(10) -0.0106(8) 0.0059(7) -0.0117(7) N21B 0.0269(8) 0.0295(9) 0.0414(9) -0.0037(7) 0.0059(7) -0.0140(7) N22B 0.0256(8) 0.0272(8) 0.0313(8) -0.0041(7) 0.0037(6) -0.0115(7) C11B 0.0276(10) 0.0284(10) 0.0327(10) -0.0068(8) 0.0009(8) -0.0110(8) C12B 0.0260(10) 0.0324(11) 0.0347(11) -0.0096(9) 0.0002(8) -0.0105(9) C13B 0.0287(10) 0.0268(10) 0.0377(11) -0.0077(8) -0.0016(8) -0.0068(8) C14B 0.0310(10) 0.0262(10) 0.0352(11) -0.0060(8) -0.0022(8) -0.0069(9) C15B 0.0424(12) 0.0310(11) 0.0432(12) -0.0038(9) 0.0055(9) -0.0124(10) C16B 0.0536(14) 0.0283(11) 0.0521(13) -0.0031(10) 0.0019(11) -0.0098(10) C17B 0.0420(13) 0.0331(12) 0.0532(14) -0.0092(10) 0.0008(10) -0.0028(10) C18B 0.0342(11) 0.0366(12) 0.0453(12) -0.0115(10) 0.0025(9) -0.0068(9) C21B 0.0279(10) 0.0272(10) 0.0317(10) -0.0035(8) 0.0024(8) -0.0129(8) C22B 0.0288(10) 0.0260(10) 0.0295(10) -0.0074(8) 0.0006(8) -0.0120(8) C23B 0.0286(10) 0.0250(10) 0.0315(10) -0.0057(8) 0.0006(8) -0.0103(8) C24B 0.0311(10) 0.0263(10) 0.0338(10) -0.0058(8) 0.0004(8) -0.0115(9) C25B 0.0444(12) 0.0300(11) 0.0425(12) -0.0041(9) 0.0068(9) -0.0181(10) C26B 0.0527(13) 0.0244(11) 0.0406(12) -0.0017(9) -0.0007(10) -0.0116(10) C27B 0.0375(11) 0.0280(11) 0.0403(12) -0.0081(9) -0.0030(9) -0.0064(9) C28B 0.0326(10) 0.0299(11) 0.0342(11) -0.0065(9) 0.0001(8) -0.0115(9) C31B 0.0280(10) 0.0287(10) 0.0401(11) -0.0056(9) 0.0039(8) -0.0100(8) C32B 0.0346(11) 0.0430(12) 0.0446(12) -0.0149(10) 0.0037(9) -0.0167(10) C33B 0.0295(11) 0.0432(12) 0.0579(14) -0.0128(11) 0.0031(10) -0.0161(10) C34B 0.0294(11) 0.0512(14) 0.0467(13) -0.0072(11) 0.0077(10) -0.0070(10) C35B 0.0396(13) 0.0720(17) 0.0513(14) -0.0328(12) -0.0001(11) -0.0055(12) C36B 0.0333(12) 0.0640(15) 0.0606(15) -0.0303(12) -0.0017(10) -0.0129(11) C41B 0.0275(10) 0.0248(10) 0.0326(10) -0.0017(8) 0.0023(8) -0.0110(8) C42B 0.0343(11) 0.0395(12) 0.0379(11) -0.0099(9) 0.0015(9) -0.0128(9) C43B 0.0398(12) 0.0457(13) 0.0397(12) -0.0108(10) 0.0059(10) -0.0065(10) C44B 0.0307(11) 0.0430(13) 0.0540(14) 0.0002(11) 0.0116(10) -0.0102(10) C45B 0.0363(12) 0.0552(14) 0.0775(17) -0.0149(13) 0.0067(11) -0.0273(11) C46B 0.0365(11) 0.0459(13) 0.0567(13) -0.0183(10) 0.0065(10) -0.0233(10) B1B 0.0336(12) 0.0285(12) 0.0369(13) -0.0023(10) 0.0070(10) -0.0118(10) N1S 0.0947(17) 0.0545(14) 0.0787(16) 0.0014(12) 0.0323(13) -0.0291(13) C1S 0.0603(15) 0.0541(16) 0.0555(15) -0.0005(12) 0.0220(12) -0.0231(13) C2S 0.0712(17) 0.0513(16) 0.0778(18) 0.0117(13) 0.0123(14) -0.0233(14) N2S 0.0618(15) 0.113(2) 0.0846(17) 0.0202(14) 0.0193(13) -0.0336(15) C3S 0.0579(17) 0.0824(19) 0.0618(17) 0.0192(14) 0.0017(14) -0.0371(15) C4S 0.0615(17) 0.101(2) 0.0746(18) 0.0000(16) 0.0170(14) -0.0394(16) _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 F1A B1A 1.386(2) . ? F2A B1A 1.396(2) . ? N11A C11A 1.358(2) . ? N11A C14A 1.413(2) . ? N11A B1A 1.538(2) . ? N12A C12A 1.279(2) . ? N12A C31A 1.417(2) . ? N21A C24A 1.369(2) . ? N21A C21A 1.380(2) . ? N22A C22A 1.339(2) . ? N22A C41A 1.450(2) . ? N22A B1A 1.555(3) . ? C11A C21A 1.361(2) . ? C11A C12A 1.478(2) . ? C12A C13A 1.473(2) . ? C13A C18A 1.394(2) . ? C13A C14A 1.400(2) . ? C14A C15A 1.381(2) . ? C15A C16A 1.389(3) . ? C16A C17A 1.387(3) . ? C17A C18A 1.382(3) . ? C21A C22A 1.431(2) . ? C22A C23A 1.441(2) . ? C23A C28A 1.406(2) . ? C23A C24A 1.415(2) . ? C24A C25A 1.389(3) . ? C25A C26A 1.371(3) . ? C26A C27A 1.404(3) . ? C27A C28A 1.374(3) . ? C31A C32A 1.381(2) . ? C31A C36A 1.381(2) . ? C32A C33A 1.382(3) . ? C33A C34A 1.377(3) . ? C34A C35A 1.370(3) . ? C35A C36A 1.381(3) . ? C41A C42A 1.374(2) . ? C41A C46A 1.375(2) . ? C42A C43A 1.379(3) . ? C43A C44A 1.370(3) . ? C44A C45A 1.372(3) . ? C45A C46A 1.386(3) . ? F1B B1B 1.382(2) . ? F2B B1B 1.402(2) . ? N11B C11B 1.362(2) . ? N11B C14B 1.413(2) . ? N11B B1B 1.528(2) . ? N12B C12B 1.282(2) . ? N12B C31B 1.419(2) . ? N21B C24B 1.375(2) . ? N21B C21B 1.377(2) . ? N22B C22B 1.341(2) . ? N22B C41B 1.441(2) . ? N22B B1B 1.564(2) . ? C11B C21B 1.368(2) . ? C11B C12B 1.474(2) . ? C12B C13B 1.472(2) . ? C13B C18B 1.394(2) . ? C13B C14B 1.400(2) . ? C14B C15B 1.390(2) . ? C15B C16B 1.386(3) . ? C16B C17B 1.389(3) . ? C17B C18B 1.380(3) . ? C21B C22B 1.421(2) . ? C22B C23B 1.439(2) . ? C23B C28B 1.410(2) . ? C23B C24B 1.410(2) . ? C24B C25B 1.392(2) . ? C25B C26B 1.374(3) . ? C26B C27B 1.400(3) . ? C27B C28B 1.373(2) . ? C31B C36B 1.377(3) . ? C31B C32B 1.382(2) . ? C32B C33B 1.385(3) . ? C33B C34B 1.373(3) . ? C34B C35B 1.373(3) . ? C35B C36B 1.383(3) . ? C41B C46B 1.375(2) . ? C41B C42B 1.382(2) . ? C42B C43B 1.388(3) . ? C43B C44B 1.377(3) . ? C44B C45B 1.372(3) . ? C45B C46B 1.387(3) . ? N1S C1S 1.130(3) . ? C1S C2S 1.456(3) . ? N2S C3S 1.126(3) . ? C3S C4S 1.461(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 C11A N11A C14A 107.52(14) . . ? C11A N11A B1A 125.04(15) . . ? C14A N11A B1A 127.43(15) . . ? C12A N12A C31A 120.75(15) . . ? C24A N21A C21A 108.64(14) . . ? C22A N22A C41A 119.46(15) . . ? C22A N22A B1A 123.79(15) . . ? C41A N22A B1A 116.67(14) . . ? N11A C11A C21A 120.65(16) . . ? N11A C11A C12A 110.54(15) . . ? C21A C11A C12A 128.81(16) . . ? N12A C12A C13A 135.85(17) . . ? N12A C12A C11A 119.89(16) . . ? C13A C12A C11A 104.18(14) . . ? C18A C13A C14A 119.69(17) . . ? C18A C13A C12A 133.69(17) . . ? C14A C13A C12A 106.53(15) . . ? C15A C14A C13A 121.82(17) . . ? C15A C14A N11A 126.94(16) . . ? C13A C14A N11A 111.22(15) . . ? C14A C15A C16A 117.51(18) . . ? C17A C16A C15A 121.50(19) . . ? C18A C17A C16A 120.72(18) . . ? C17A C18A C13A 118.74(17) . . ? C11A C21A N21A 129.47(16) . . ? C11A C21A C22A 121.54(16) . . ? N21A C21A C22A 108.98(15) . . ? N22A C22A C21A 120.70(16) . . ? N22A C22A C23A 133.16(16) . . ? C21A C22A C23A 106.14(15) . . ? C28A C23A C24A 119.10(17) . . ? C28A C23A C22A 134.66(17) . . ? C24A C23A C22A 106.14(16) . . ? N21A C24A C25A 128.14(17) . . ? N21A C24A C23A 110.05(16) . . ? C25A C24A C23A 121.82(17) . . ? C26A C25A C24A 117.64(18) . . ? C25A C26A C27A 121.68(19) . . ? C28A C27A C26A 121.05(19) . . ? C27A C28A C23A 118.66(18) . . ? C32A C31A C36A 118.92(17) . . ? C32A C31A N12A 121.13(17) . . ? C36A C31A N12A 119.74(16) . . ? C31A C32A C33A 120.52(19) . . ? C34A C33A C32A 120.02(19) . . ? C35A C34A C33A 119.80(19) . . ? C34A C35A C36A 120.27(19) . . ? C35A C36A C31A 120.46(19) . . ? C42A C41A C46A 120.03(17) . . ? C42A C41A N22A 119.81(16) . . ? C46A C41A N22A 120.14(16) . . ? C41A C42A C43A 119.93(18) . . ? C44A C43A C42A 120.47(19) . . ? C43A C44A C45A 119.57(19) . . ? C44A C45A C46A 120.48(19) . . ? C41A C46A C45A 119.51(19) . . ? F1A B1A F2A 108.17(16) . . ? F1A B1A N11A 110.19(16) . . ? F2A B1A N11A 110.21(16) . . ? F1A B1A N22A 110.03(16) . . ? F2A B1A N22A 110.08(16) . . ? N11A B1A N22A 108.16(15) . . ? C11B N11B C14B 107.45(14) . . ? C11B N11B B1B 124.48(14) . . ? C14B N11B B1B 127.72(15) . . ? C12B N12B C31B 121.12(15) . . ? C24B N21B C21B 108.13(14) . . ? C22B N22B C41B 119.05(14) . . ? C22B N22B B1B 122.98(14) . . ? C41B N22B B1B 117.96(13) . . ? N11B C11B C21B 120.63(15) . . ? N11B C11B C12B 110.48(15) . . ? C21B C11B C12B 128.77(16) . . ? N12B C12B C13B 135.94(16) . . ? N12B C12B C11B 119.70(16) . . ? C13B C12B C11B 104.35(15) . . ? C18B C13B C14B 119.90(17) . . ? C18B C13B C12B 133.54(17) . . ? C14B C13B C12B 106.54(15) . . ? C15B C14B C13B 121.68(17) . . ? C15B C14B N11B 127.14(17) . . ? C13B C14B N11B 111.16(15) . . ? C16B C15B C14B 117.04(18) . . ? C15B C16B C17B 122.10(19) . . ? C18B C17B C16B 120.43(19) . . ? C17B C18B C13B 118.82(19) . . ? C11B C21B N21B 128.92(16) . . ? C11B C21B C22B 121.78(16) . . ? N21B C21B C22B 109.28(15) . . ? N22B C22B C21B 120.69(15) . . ? N22B C22B C23B 132.88(15) . . ? C21B C22B C23B 106.39(14) . . ? C28B C23B C24B 119.04(16) . . ? C28B C23B C22B 134.76(16) . . ? C24B C23B C22B 105.98(14) . . ? N21B C24B C25B 127.69(16) . . ? N21B C24B C23B 110.16(15) . . ? C25B C24B C23B 122.13(16) . . ? C26B C25B C24B 117.21(17) . . ? C25B C26B C27B 121.93(18) . . ? C28B C27B C26B 121.06(18) . . ? C27B C28B C23B 118.58(17) . . ? C36B C31B C32B 119.71(17) . . ? C36B C31B N12B 120.25(16) . . ? C32B C31B N12B 119.75(16) . . ? C31B C32B C33B 119.83(18) . . ? C34B C33B C32B 120.42(18) . . ? C33B C34B C35B 119.55(19) . . ? C34B C35B C36B 120.5(2) . . ? C31B C36B C35B 119.95(19) . . ? C46B C41B C42B 120.17(17) . . ? C46B C41B N22B 120.42(16) . . ? C42B C41B N22B 119.41(15) . . ? C41B C42B C43B 120.06(18) . . ? C44B C43B C42B 119.93(19) . . ? C45B C44B C43B 119.48(19) . . ? C44B C45B C46B 121.19(19) . . ? C41B C46B C45B 119.16(19) . . ? F1B B1B F2B 108.22(16) . . ? F1B B1B N11B 111.30(16) . . ? F2B B1B N11B 109.92(15) . . ? F1B B1B N22B 110.13(15) . . ? F2B B1B N22B 108.66(15) . . ? N11B B1B N22B 108.59(14) . . ? N1S C1S C2S 179.4(3) . . ? N2S C3S C4S 179.8(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14A N11A C11A C21A -179.66(16) . . . . ? B1A N11A C11A C21A -0.4(3) . . . . ? C14A N11A C11A C12A -0.30(19) . . . . ? B1A N11A C11A C12A 178.92(16) . . . . ? C31A N12A C12A C13A 5.3(3) . . . . ? C31A N12A C12A C11A -178.58(16) . . . . ? N11A C11A C12A N12A -176.47(16) . . . . ? C21A C11A C12A N12A 2.8(3) . . . . ? N11A C11A C12A C13A 0.73(19) . . . . ? C21A C11A C12A C13A -179.97(18) . . . . ? N12A C12A C13A C18A -0.9(4) . . . . ? C11A C12A C13A C18A -177.40(19) . . . . ? N12A C12A C13A C14A 175.6(2) . . . . ? C11A C12A C13A C14A -0.88(19) . . . . ? C18A C13A C14A C15A -0.5(3) . . . . ? C12A C13A C14A C15A -177.66(17) . . . . ? C18A C13A C14A N11A 177.87(16) . . . . ? C12A C13A C14A N11A 0.8(2) . . . . ? C11A N11A C14A C15A 178.02(18) . . . . ? B1A N11A C14A C15A -1.2(3) . . . . ? C11A N11A C14A C13A -0.3(2) . . . . ? B1A N11A C14A C13A -179.49(17) . . . . ? C13A C14A C15A C16A 1.5(3) . . . . ? N11A C14A C15A C16A -176.63(18) . . . . ? C14A C15A C16A C17A -1.2(3) . . . . ? C15A C16A C17A C18A -0.1(3) . . . . ? C16A C17A C18A C13A 1.1(3) . . . . ? C14A C13A C18A C17A -0.8(3) . . . . ? C12A C13A C18A C17A 175.40(19) . . . . ? N11A C11A C21A N21A -178.89(17) . . . . ? C12A C11A C21A N21A 1.9(3) . . . . ? N11A C11A C21A C22A -0.6(3) . . . . ? C12A C11A C21A C22A -179.86(17) . . . . ? C24A N21A C21A C11A -179.28(18) . . . . ? C24A N21A C21A C22A 2.3(2) . . . . ? C41A N22A C22A C21A -173.09(16) . . . . ? B1A N22A C22A C21A 3.7(3) . . . . ? C41A N22A C22A C23A 6.0(3) . . . . ? B1A N22A C22A C23A -177.18(18) . . . . ? C11A C21A C22A N22A -1.0(3) . . . . ? N21A C21A C22A N22A 177.56(15) . . . . ? C11A C21A C22A C23A 179.64(16) . . . . ? N21A C21A C22A C23A -1.8(2) . . . . ? N22A C22A C23A C28A 5.2(4) . . . . ? C21A C22A C23A C28A -175.5(2) . . . . ? N22A C22A C23A C24A -178.60(18) . . . . ? C21A C22A C23A C24A 0.61(19) . . . . ? C21A N21A C24A C25A 178.37(18) . . . . ? C21A N21A C24A C23A -1.9(2) . . . . ? C28A C23A C24A N21A 177.64(16) . . . . ? C22A C23A C24A N21A 0.8(2) . . . . ? C28A C23A C24A C25A -2.6(3) . . . . ? C22A C23A C24A C25A -179.48(17) . . . . ? N21A C24A C25A C26A -177.83(18) . . . . ? C23A C24A C25A C26A 2.5(3) . . . . ? C24A C25A C26A C27A -0.6(3) . . . . ? C25A C26A C27A C28A -1.1(3) . . . . ? C26A C27A C28A C23A 1.0(3) . . . . ? C24A C23A C28A C27A 0.8(3) . . . . ? C22A C23A C28A C27A 176.60(19) . . . . ? C12A N12A C31A C32A 75.3(2) . . . . ? C12A N12A C31A C36A -110.0(2) . . . . ? C36A C31A C32A C33A 0.9(3) . . . . ? N12A C31A C32A C33A 175.65(17) . . . . ? C31A C32A C33A C34A -0.4(3) . . . . ? C32A C33A C34A C35A 0.3(3) . . . . ? C33A C34A C35A C36A -0.6(3) . . . . ? C34A C35A C36A C31A 1.1(3) . . . . ? C32A C31A C36A C35A -1.2(3) . . . . ? N12A C31A C36A C35A -176.04(17) . . . . ? C22A N22A C41A C42A 81.4(2) . . . . ? B1A N22A C41A C42A -95.6(2) . . . . ? C22A N22A C41A C46A -100.2(2) . . . . ? B1A N22A C41A C46A 82.8(2) . . . . ? C46A C41A C42A C43A 0.2(3) . . . . ? N22A C41A C42A C43A 178.65(18) . . . . ? C41A C42A C43A C44A -0.1(3) . . . . ? C42A C43A C44A C45A 0.1(3) . . . . ? C43A C44A C45A C46A -0.3(3) . . . . ? C42A C41A C46A C45A -0.4(3) . . . . ? N22A C41A C46A C45A -178.83(18) . . . . ? C44A C45A C46A C41A 0.5(3) . . . . ? C11A N11A B1A F1A 122.88(18) . . . . ? C14A N11A B1A F1A -58.1(2) . . . . ? C11A N11A B1A F2A -117.82(19) . . . . ? C14A N11A B1A F2A 61.2(2) . . . . ? C11A N11A B1A N22A 2.6(2) . . . . ? C14A N11A B1A N22A -178.37(15) . . . . ? C22A N22A B1A F1A -124.61(17) . . . . ? C41A N22A B1A F1A 52.3(2) . . . . ? C22A N22A B1A F2A 116.27(18) . . . . ? C41A N22A B1A F2A -66.9(2) . . . . ? C22A N22A B1A N11A -4.2(2) . . . . ? C41A N22A B1A N11A 172.69(14) . . . . ? C14B N11B C11B C21B -176.37(16) . . . . ? B1B N11B C11B C21B -2.7(3) . . . . ? C14B N11B C11B C12B -0.04(19) . . . . ? B1B N11B C11B C12B 173.62(15) . . . . ? C31B N12B C12B C13B -6.3(3) . . . . ? C31B N12B C12B C11B 173.75(15) . . . . ? N11B C11B C12B N12B 179.59(15) . . . . ? C21B C11B C12B N12B -4.5(3) . . . . ? N11B C11B C12B C13B -0.37(19) . . . . ? C21B C11B C12B C13B 175.58(17) . . . . ? N12B C12B C13B C18B -1.0(4) . . . . ? C11B C12B C13B C18B 178.9(2) . . . . ? N12B C12B C13B C14B -179.3(2) . . . . ? C11B C12B C13B C14B 0.64(19) . . . . ? C18B C13B C14B C15B 1.9(3) . . . . ? C12B C13B C14B C15B -179.54(16) . . . . ? C18B C13B C14B N11B -179.27(16) . . . . ? C12B C13B C14B N11B -0.7(2) . . . . ? C11B N11B C14B C15B 179.24(18) . . . . ? B1B N11B C14B C15B 5.8(3) . . . . ? C11B N11B C14B C13B 0.5(2) . . . . ? B1B N11B C14B C13B -172.92(16) . . . . ? C13B C14B C15B C16B -1.7(3) . . . . ? N11B C14B C15B C16B 179.64(18) . . . . ? C14B C15B C16B C17B 0.6(3) . . . . ? C15B C16B C17B C18B 0.4(3) . . . . ? C16B C17B C18B C13B -0.2(3) . . . . ? C14B C13B C18B C17B -0.9(3) . . . . ? C12B C13B C18B C17B -178.97(19) . . . . ? N11B C11B C21B N21B 176.82(16) . . . . ? C12B C11B C21B N21B 1.2(3) . . . . ? N11B C11B C21B C22B -1.1(3) . . . . ? C12B C11B C21B C22B -176.69(16) . . . . ? C24B N21B C21B C11B -175.62(18) . . . . ? C24B N21B C21B C22B 2.51(19) . . . . ? C41B N22B C22B C21B -172.69(15) . . . . ? B1B N22B C22B C21B 8.7(2) . . . . ? C41B N22B C22B C23B 9.7(3) . . . . ? B1B N22B C22B C23B -168.94(18) . . . . ? C11B C21B C22B N22B -2.0(3) . . . . ? N21B C21B C22B N22B 179.71(14) . . . . ? C11B C21B C22B C23B 176.18(16) . . . . ? N21B C21B C22B C23B -2.11(19) . . . . ? N22B C22B C23B C28B 4.4(3) . . . . ? C21B C22B C23B C28B -173.42(19) . . . . ? N22B C22B C23B C24B 178.77(17) . . . . ? C21B C22B C23B C24B 0.91(18) . . . . ? C21B N21B C24B C25B 176.60(17) . . . . ? C21B N21B C24B C23B -1.93(19) . . . . ? C28B C23B C24B N21B 176.00(15) . . . . ? C22B C23B C24B N21B 0.60(19) . . . . ? C28B C23B C24B C25B -2.6(3) . . . . ? C22B C23B C24B C25B -178.03(16) . . . . ? N21B C24B C25B C26B -176.58(17) . . . . ? C23B C24B C25B C26B 1.8(3) . . . . ? C24B C25B C26B C27B 0.1(3) . . . . ? C25B C26B C27B C28B -1.1(3) . . . . ? C26B C27B C28B C23B 0.2(3) . . . . ? C24B C23B C28B C27B 1.5(2) . . . . ? C22B C23B C28B C27B 175.31(18) . . . . ? C12B N12B C31B C36B -76.5(2) . . . . ? C12B N12B C31B C32B 109.8(2) . . . . ? C36B C31B C32B C33B 0.6(3) . . . . ? N12B C31B C32B C33B 174.40(17) . . . . ? C31B C32B C33B C34B -2.1(3) . . . . ? C32B C33B C34B C35B 2.2(3) . . . . ? C33B C34B C35B C36B -0.7(3) . . . . ? C32B C31B C36B C35B 0.8(3) . . . . ? N12B C31B C36B C35B -172.94(19) . . . . ? C34B C35B C36B C31B -0.8(3) . . . . ? C22B N22B C41B C46B -109.48(19) . . . . ? B1B N22B C41B C46B 69.2(2) . . . . ? C22B N22B C41B C42B 71.0(2) . . . . ? B1B N22B C41B C42B -110.25(19) . . . . ? C46B C41B C42B C43B 0.3(3) . . . . ? N22B C41B C42B C43B 179.76(16) . . . . ? C41B C42B C43B C44B 0.0(3) . . . . ? C42B C43B C44B C45B 0.0(3) . . . . ? C43B C44B C45B C46B -0.3(3) . . . . ? C42B C41B C46B C45B -0.5(3) . . . . ? N22B C41B C46B C45B -179.99(17) . . . . ? C44B C45B C46B C41B 0.5(3) . . . . ? C11B N11B B1B F1B 129.32(17) . . . . ? C14B N11B B1B F1B -58.3(2) . . . . ? C11B N11B B1B F2B -110.80(18) . . . . ? C14B N11B B1B F2B 61.6(2) . . . . ? C11B N11B B1B N22B 7.9(2) . . . . ? C14B N11B B1B N22B -179.70(15) . . . . ? C22B N22B B1B F1B -133.00(16) . . . . ? C41B N22B B1B F1B 48.3(2) . . . . ? C22B N22B B1B F2B 108.63(17) . . . . ? C41B N22B B1B F2B -70.02(19) . . . . ? C22B N22B B1B N11B -10.9(2) . . . . ? C41B N22B B1B N11B 170.45(14) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.84 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.233 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.055 # Attachment '- 2b.cif' data_rh088 _database_code_depnum_ccdc_archive 'CCDC 895625' #TrackingRef '- 2b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30.50 H24 B Cl F2 N4' _chemical_formula_weight 530.80 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' 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 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 33.428(2) _cell_length_b 11.5134(7) _cell_length_c 13.9925(9) _cell_angle_alpha 90.00 _cell_angle_beta 111.419(3) _cell_angle_gamma 90.00 _cell_volume 5013.4(5) _cell_formula_units_Z 8 _cell_measurement_temperature 103.0(1) _cell_measurement_reflns_used 4596 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 23.01 _exptl_crystal_description blade _exptl_crystal_colour blue _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2200 _exptl_absorpt_coefficient_mu 0.197 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.853 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_process_details 'SADABS, Sheldrick (2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103.0(1) _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 X8 APEX II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17041 _diffrn_reflns_av_R_equivalents 0.0642 _diffrn_reflns_av_sigmaI/netI 0.0611 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 23.08 _reflns_number_total 3521 _reflns_number_gt 2278 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0503P)^2^+15.9227P] 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 3521 _refine_ls_number_parameters 354 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1025 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1374 _refine_ls_wR_factor_gt 0.1127 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 C11 C 0.22613(11) 0.0677(3) 0.1386(3) 0.0159(9) Uani 1 1 d . . . C12 C 0.18088(11) 0.0581(3) 0.1273(3) 0.0172(9) Uani 1 1 d . . . C13 C 0.17172(11) -0.0672(3) 0.1154(3) 0.0170(9) Uani 1 1 d . . . C14 C 0.21004(11) -0.1205(3) 0.1209(3) 0.0179(9) Uani 1 1 d . . . C15 C 0.21254(12) -0.2398(3) 0.1109(3) 0.0198(9) Uani 1 1 d . . . H15 H 0.2384 -0.2757 0.1131 0.024 Uiso 1 1 calc R . . C16 C 0.17618(12) -0.3044(3) 0.0975(3) 0.0248(10) Uani 1 1 d . . . H16 H 0.1771 -0.3863 0.0903 0.030 Uiso 1 1 calc R . . C17 C 0.13847(12) -0.2526(3) 0.0944(3) 0.0255(10) Uani 1 1 d . . . H17 H 0.1140 -0.2995 0.0858 0.031 Uiso 1 1 calc R . . C18 C 0.13583(12) -0.1333(3) 0.1036(3) 0.0229(10) Uani 1 1 d . . . H18 H 0.1099 -0.0979 0.1019 0.027 Uiso 1 1 calc R . . C21 C 0.25029(11) 0.1647(3) 0.1435(3) 0.0158(9) Uani 1 1 d . . . C22 C 0.29163(11) 0.1605(3) 0.1398(3) 0.0158(9) Uani 1 1 d . . . C23 C 0.30441(11) 0.2787(3) 0.1337(3) 0.0159(9) Uani 1 1 d . . . C24 C 0.26968(11) 0.3476(3) 0.1352(3) 0.0180(9) Uani 1 1 d . . . C25 C 0.27032(12) 0.4688(3) 0.1294(3) 0.0186(9) Uani 1 1 d . . . H25 H 0.2463 0.5139 0.1282 0.022 Uiso 1 1 calc R . . C26 C 0.30662(12) 0.5202(3) 0.1256(3) 0.0201(9) Uani 1 1 d . . . H26 H 0.3078 0.6024 0.1211 0.024 Uiso 1 1 calc R . . C27 C 0.34214(12) 0.4540(3) 0.1280(3) 0.0216(9) Uani 1 1 d . . . H27 H 0.3672 0.4921 0.1272 0.026 Uiso 1 1 calc R . . C28 C 0.34128(12) 0.3340(3) 0.1317(3) 0.0206(9) Uani 1 1 d . . . H28 H 0.3654 0.2898 0.1329 0.025 Uiso 1 1 calc R . . C31 C 0.11747(11) 0.1507(3) 0.1240(3) 0.0191(9) Uani 1 1 d . . . C32 C 0.10616(12) 0.2029(3) 0.1998(3) 0.0240(10) Uani 1 1 d . . . H32 H 0.1278 0.2336 0.2593 0.029 Uiso 1 1 calc R . . C33 C 0.06368(12) 0.2106(3) 0.1891(3) 0.0281(10) Uani 1 1 d . . . H33 H 0.0566 0.2441 0.2430 0.034 Uiso 1 1 calc R . . C34 C 0.03095(12) 0.1708(3) 0.1021(3) 0.0257(10) Uani 1 1 d . . . C35 C 0.04273(12) 0.1221(3) 0.0258(3) 0.0255(10) Uani 1 1 d . . . H35 H 0.0210 0.0950 -0.0353 0.031 Uiso 1 1 calc R . . C36 C 0.08509(11) 0.1121(3) 0.0360(3) 0.0226(9) Uani 1 1 d . . . H36 H 0.0922 0.0785 -0.0178 0.027 Uiso 1 1 calc R . . C37 C -0.01539(12) 0.1804(4) 0.0910(3) 0.0386(12) Uani 1 1 d . . . H37A H -0.0337 0.1747 0.0183 0.058 Uiso 1 1 calc R . . H37B H -0.0202 0.2553 0.1183 0.058 Uiso 1 1 calc R . . H37C H -0.0224 0.1173 0.1292 0.058 Uiso 1 1 calc R . . C41 C 0.35039(11) 0.0519(3) 0.1250(3) 0.0176(9) Uani 1 1 d . . . C42 C 0.38679(12) 0.0040(4) 0.1966(3) 0.0315(11) Uani 1 1 d . . . H42 H 0.3864 -0.0238 0.2601 0.038 Uiso 1 1 calc R . . C43 C 0.42382(13) -0.0033(4) 0.1753(3) 0.0378(12) Uani 1 1 d . . . H43 H 0.4488 -0.0366 0.2249 0.045 Uiso 1 1 calc R . . C44 C 0.42569(13) 0.0363(3) 0.0843(3) 0.0300(11) Uani 1 1 d . . . C45 C 0.38906(12) 0.0835(3) 0.0137(3) 0.0245(10) Uani 1 1 d . . . H45 H 0.3896 0.1118 -0.0496 0.029 Uiso 1 1 calc R . . C46 C 0.35173(12) 0.0906(3) 0.0328(3) 0.0206(9) Uani 1 1 d . . . H46 H 0.3266 0.1223 -0.0176 0.025 Uiso 1 1 calc R . . C47 C 0.46603(14) 0.0270(4) 0.0601(4) 0.0495(14) Uani 1 1 d . . . H47A H 0.4908 0.0146 0.1238 0.074 Uiso 1 1 calc R . . H47B H 0.4701 0.0990 0.0273 0.074 Uiso 1 1 calc R . . H47C H 0.4634 -0.0385 0.0136 0.074 Uiso 1 1 calc R . . C48 C 0.0000 0.2080(7) -0.2500 0.098(4) Uani 1 2 d S . . H48A H 0.0112 0.2583 -0.1886 0.117 Uiso 0.50 1 calc PR . . H48B H -0.0112 0.2583 -0.3114 0.117 Uiso 0.50 1 calc PR . . B1 B 0.29160(13) -0.0578(4) 0.1653(3) 0.0185(10) Uani 1 1 d . . . N11 N 0.24329(9) -0.0390(3) 0.1374(2) 0.0172(7) Uani 1 1 d . . . N12 N 0.16105(9) 0.1513(3) 0.1360(2) 0.0178(7) Uani 1 1 d . . . N21 N 0.23737(10) 0.2793(3) 0.1408(2) 0.0175(8) Uani 1 1 d . . . N22 N 0.31102(9) 0.0574(3) 0.1426(2) 0.0168(7) Uani 1 1 d . . . F1 F 0.31102(6) -0.08140(18) 0.27145(15) 0.0248(6) Uani 1 1 d . . . F2 F 0.29971(6) -0.14837(18) 0.11152(16) 0.0265(6) Uani 1 1 d . . . Cl1 Cl -0.04131(5) 0.1193(2) -0.24169(12) 0.1013(7) Uani 1 1 d . . . H21N H 0.2142(12) 0.303(3) 0.157(3) 0.025(11) 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 C11 0.016(2) 0.020(2) 0.012(2) 0.0008(17) 0.0044(16) 0.0027(18) C12 0.016(2) 0.023(2) 0.012(2) -0.0004(18) 0.0049(16) -0.0004(19) C13 0.017(2) 0.018(2) 0.016(2) 0.0010(17) 0.0062(16) -0.0017(18) C14 0.017(2) 0.023(2) 0.013(2) -0.0014(18) 0.0056(16) -0.0044(18) C15 0.020(2) 0.019(2) 0.023(2) -0.0006(19) 0.0111(18) 0.0010(18) C16 0.029(2) 0.018(2) 0.028(2) -0.0017(19) 0.0117(19) -0.002(2) C17 0.019(2) 0.027(3) 0.030(2) -0.002(2) 0.0084(18) -0.0074(19) C18 0.020(2) 0.025(2) 0.022(2) 0.0029(19) 0.0065(18) -0.0001(19) C21 0.016(2) 0.015(2) 0.016(2) 0.0010(17) 0.0063(16) 0.0021(18) C22 0.015(2) 0.019(2) 0.013(2) -0.0010(17) 0.0041(16) 0.0004(18) C23 0.015(2) 0.020(2) 0.013(2) 0.0001(17) 0.0060(16) -0.0001(17) C24 0.019(2) 0.023(2) 0.012(2) 0.0012(18) 0.0049(16) -0.0002(19) C25 0.023(2) 0.016(2) 0.018(2) -0.0008(18) 0.0092(17) 0.0017(18) C26 0.029(2) 0.017(2) 0.016(2) -0.0002(17) 0.0092(18) -0.0027(19) C27 0.023(2) 0.024(2) 0.020(2) 0.0017(18) 0.0104(18) -0.0037(19) C28 0.022(2) 0.025(2) 0.018(2) 0.0012(19) 0.0113(17) 0.0038(19) C31 0.017(2) 0.016(2) 0.027(2) 0.0032(18) 0.0114(18) -0.0010(17) C32 0.022(2) 0.026(2) 0.025(2) -0.0024(19) 0.0098(18) -0.0006(19) C33 0.029(2) 0.027(3) 0.037(3) -0.004(2) 0.023(2) 0.002(2) C34 0.018(2) 0.022(2) 0.040(3) 0.001(2) 0.014(2) 0.0017(19) C35 0.024(2) 0.022(2) 0.028(2) 0.000(2) 0.0061(19) -0.0016(19) C36 0.021(2) 0.025(2) 0.026(2) 0.0000(19) 0.0139(19) 0.0011(18) C37 0.027(2) 0.037(3) 0.056(3) -0.004(2) 0.020(2) 0.000(2) C41 0.018(2) 0.014(2) 0.024(2) 0.0003(18) 0.0103(18) 0.0012(17) C42 0.024(2) 0.038(3) 0.035(3) 0.015(2) 0.014(2) 0.004(2) C43 0.021(2) 0.042(3) 0.052(3) 0.019(2) 0.015(2) 0.013(2) C44 0.031(3) 0.020(2) 0.050(3) 0.006(2) 0.027(2) 0.005(2) C45 0.035(2) 0.019(2) 0.026(2) -0.0006(19) 0.019(2) -0.002(2) C46 0.019(2) 0.021(2) 0.025(2) -0.0004(18) 0.0123(18) -0.0003(18) C47 0.043(3) 0.044(3) 0.079(4) 0.016(3) 0.043(3) 0.010(2) C48 0.205(12) 0.029(5) 0.046(5) 0.000 0.030(6) 0.000 B1 0.020(2) 0.018(3) 0.021(3) 0.001(2) 0.011(2) 0.000(2) N11 0.0179(17) 0.0173(18) 0.0173(17) 0.0000(14) 0.0077(13) -0.0004(15) N12 0.0174(17) 0.0188(19) 0.0207(18) 0.0013(15) 0.0110(14) 0.0025(15) N21 0.0130(17) 0.0187(19) 0.0241(19) 0.0009(15) 0.0107(15) 0.0033(15) N22 0.0154(17) 0.0170(18) 0.0207(18) 0.0022(15) 0.0097(14) 0.0011(14) F1 0.0198(11) 0.0296(14) 0.0251(13) 0.0074(10) 0.0083(10) -0.0013(10) F2 0.0280(12) 0.0193(13) 0.0391(14) -0.0056(11) 0.0205(11) 0.0011(10) Cl1 0.0436(9) 0.199(2) 0.0509(9) 0.0136(11) 0.0051(7) 0.0000(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C11 N11 1.358(5) . ? C11 C21 1.366(5) . ? C11 C12 1.466(5) . ? C12 N12 1.290(5) . ? C12 C13 1.472(5) . ? C13 C18 1.379(5) . ? C13 C14 1.397(5) . ? C14 C15 1.386(5) . ? C14 N11 1.408(4) . ? C15 C16 1.379(5) . ? C15 H15 0.9500 . ? C16 C17 1.381(5) . ? C16 H16 0.9500 . ? C17 C18 1.386(5) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C21 N21 1.384(5) . ? C21 C22 1.403(5) . ? C22 N22 1.346(5) . ? C22 C23 1.438(5) . ? C23 C28 1.397(5) . ? C23 C24 1.413(5) . ? C24 N21 1.362(5) . ? C24 C25 1.398(5) . ? C25 C26 1.369(5) . ? C25 H25 0.9500 . ? C26 C27 1.401(5) . ? C26 H26 0.9500 . ? C27 C28 1.383(5) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C31 C36 1.382(5) . ? C31 C32 1.387(5) . ? C31 N12 1.404(4) . ? C32 C33 1.375(5) . ? C32 H32 0.9500 . ? C33 C34 1.384(5) . ? C33 H33 0.9500 . ? C34 C35 1.384(5) . ? C34 C37 1.503(5) . ? C35 C36 1.375(5) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C41 C42 1.378(5) . ? C41 C46 1.380(5) . ? C41 N22 1.426(4) . ? C42 C43 1.377(5) . ? C42 H42 0.9500 . ? C43 C44 1.375(6) . ? C43 H43 0.9500 . ? C44 C45 1.374(5) . ? C44 C47 1.509(5) . ? C45 C46 1.371(5) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? C48 Cl1 1.755(5) . ? C48 Cl1 1.755(5) 2_554 ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? B1 F2 1.370(5) . ? B1 F1 1.413(5) . ? B1 N11 1.532(5) . ? B1 N22 1.559(5) . ? N21 H21N 0.93(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 N11 C11 C21 119.7(3) . . ? N11 C11 C12 110.8(3) . . ? C21 C11 C12 129.4(3) . . ? N12 C12 C11 118.2(3) . . ? N12 C12 C13 137.1(3) . . ? C11 C12 C13 104.4(3) . . ? C18 C13 C14 120.3(3) . . ? C18 C13 C12 133.7(3) . . ? C14 C13 C12 106.0(3) . . ? C15 C14 C13 121.2(3) . . ? C15 C14 N11 127.1(3) . . ? C13 C14 N11 111.7(3) . . ? C16 C15 C14 117.8(3) . . ? C16 C15 H15 121.1 . . ? C14 C15 H15 121.1 . . ? C15 C16 C17 121.4(4) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C16 C17 C18 120.9(4) . . ? C16 C17 H17 119.5 . . ? C18 C17 H17 119.5 . . ? C13 C18 C17 118.4(4) . . ? C13 C18 H18 120.8 . . ? C17 C18 H18 120.8 . . ? C11 C21 N21 127.3(3) . . ? C11 C21 C22 122.8(3) . . ? N21 C21 C22 109.5(3) . . ? N22 C22 C21 120.0(3) . . ? N22 C22 C23 133.3(3) . . ? C21 C22 C23 106.7(3) . . ? C28 C23 C24 118.7(3) . . ? C28 C23 C22 135.7(3) . . ? C24 C23 C22 105.5(3) . . ? N21 C24 C25 127.6(3) . . ? N21 C24 C23 110.4(3) . . ? C25 C24 C23 122.0(3) . . ? C26 C25 C24 117.8(3) . . ? C26 C25 H25 121.1 . . ? C24 C25 H25 121.1 . . ? C25 C26 C27 121.3(4) . . ? C25 C26 H26 119.4 . . ? C27 C26 H26 119.4 . . ? C28 C27 C26 121.0(4) . . ? C28 C27 H27 119.5 . . ? C26 C27 H27 119.5 . . ? C27 C28 C23 119.1(3) . . ? C27 C28 H28 120.4 . . ? C23 C28 H28 120.4 . . ? C36 C31 C32 118.5(3) . . ? C36 C31 N12 123.3(3) . . ? C32 C31 N12 117.8(3) . . ? C33 C32 C31 120.2(4) . . ? C33 C32 H32 119.9 . . ? C31 C32 H32 119.9 . . ? C32 C33 C34 121.8(4) . . ? C32 C33 H33 119.1 . . ? C34 C33 H33 119.1 . . ? C33 C34 C35 117.1(3) . . ? C33 C34 C37 121.4(4) . . ? C35 C34 C37 121.5(4) . . ? C36 C35 C34 121.7(4) . . ? C36 C35 H35 119.1 . . ? C34 C35 H35 119.1 . . ? C35 C36 C31 120.5(4) . . ? C35 C36 H36 119.8 . . ? C31 C36 H36 119.8 . . ? C34 C37 H37A 109.5 . . ? C34 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C34 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C42 C41 C46 119.1(3) . . ? C42 C41 N22 121.2(3) . . ? C46 C41 N22 119.6(3) . . ? C43 C42 C41 119.5(4) . . ? C43 C42 H42 120.3 . . ? C41 C42 H42 120.3 . . ? C44 C43 C42 121.9(4) . . ? C44 C43 H43 119.0 . . ? C42 C43 H43 119.0 . . ? C45 C44 C43 117.8(4) . . ? C45 C44 C47 120.1(4) . . ? C43 C44 C47 122.0(4) . . ? C46 C45 C44 121.2(4) . . ? C46 C45 H45 119.4 . . ? C44 C45 H45 119.4 . . ? C45 C46 C41 120.4(4) . . ? C45 C46 H46 119.8 . . ? C41 C46 H46 119.8 . . ? C44 C47 H47A 109.5 . . ? C44 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C44 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? Cl1 C48 Cl1 108.9(4) . 2_554 ? Cl1 C48 H48A 109.9 . . ? Cl1 C48 H48A 109.9 2_554 . ? Cl1 C48 H48B 109.9 . . ? Cl1 C48 H48B 109.9 2_554 . ? H48A C48 H48B 108.3 . . ? F2 B1 F1 108.9(3) . . ? F2 B1 N11 111.7(3) . . ? F1 B1 N11 109.4(3) . . ? F2 B1 N22 110.8(3) . . ? F1 B1 N22 108.2(3) . . ? N11 B1 N22 107.9(3) . . ? C11 N11 C14 107.0(3) . . ? C11 N11 B1 122.3(3) . . ? C14 N11 B1 130.1(3) . . ? C12 N12 C31 122.1(3) . . ? C24 N21 C21 107.8(3) . . ? C24 N21 H21N 126(2) . . ? C21 N21 H21N 124(2) . . ? C22 N22 C41 119.9(3) . . ? C22 N22 B1 121.6(3) . . ? C41 N22 B1 118.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N11 C11 C12 N12 174.0(3) . . . . ? C21 C11 C12 N12 -10.2(6) . . . . ? N11 C11 C12 C13 -1.9(4) . . . . ? C21 C11 C12 C13 173.9(3) . . . . ? N12 C12 C13 C18 3.9(7) . . . . ? C11 C12 C13 C18 178.6(4) . . . . ? N12 C12 C13 C14 -174.3(4) . . . . ? C11 C12 C13 C14 0.4(4) . . . . ? C18 C13 C14 C15 2.4(5) . . . . ? C12 C13 C14 C15 -179.1(3) . . . . ? C18 C13 C14 N11 -177.3(3) . . . . ? C12 C13 C14 N11 1.2(4) . . . . ? C13 C14 C15 C16 -1.4(5) . . . . ? N11 C14 C15 C16 178.4(3) . . . . ? C14 C15 C16 C17 -0.1(6) . . . . ? C15 C16 C17 C18 0.6(6) . . . . ? C14 C13 C18 C17 -1.9(5) . . . . ? C12 C13 C18 C17 -179.9(4) . . . . ? C16 C17 C18 C13 0.4(6) . . . . ? N11 C11 C21 N21 176.9(3) . . . . ? C12 C11 C21 N21 1.4(6) . . . . ? N11 C11 C21 C22 4.9(5) . . . . ? C12 C11 C21 C22 -170.6(3) . . . . ? C11 C21 C22 N22 -7.5(5) . . . . ? N21 C21 C22 N22 179.3(3) . . . . ? C11 C21 C22 C23 172.8(3) . . . . ? N21 C21 C22 C23 -0.4(4) . . . . ? N22 C22 C23 C28 -2.5(7) . . . . ? C21 C22 C23 C28 177.2(4) . . . . ? N22 C22 C23 C24 -179.1(4) . . . . ? C21 C22 C23 C24 0.5(4) . . . . ? C28 C23 C24 N21 -177.8(3) . . . . ? C22 C23 C24 N21 -0.5(4) . . . . ? C28 C23 C24 C25 3.4(5) . . . . ? C22 C23 C24 C25 -179.3(3) . . . . ? N21 C24 C25 C26 179.2(3) . . . . ? C23 C24 C25 C26 -2.1(5) . . . . ? C24 C25 C26 C27 -0.4(5) . . . . ? C25 C26 C27 C28 1.7(5) . . . . ? C26 C27 C28 C23 -0.5(5) . . . . ? C24 C23 C28 C27 -2.0(5) . . . . ? C22 C23 C28 C27 -178.3(4) . . . . ? C36 C31 C32 C33 3.1(6) . . . . ? N12 C31 C32 C33 176.4(4) . . . . ? C31 C32 C33 C34 -2.3(6) . . . . ? C32 C33 C34 C35 0.3(6) . . . . ? C32 C33 C34 C37 -179.6(4) . . . . ? C33 C34 C35 C36 0.8(6) . . . . ? C37 C34 C35 C36 -179.3(4) . . . . ? C34 C35 C36 C31 0.1(6) . . . . ? C32 C31 C36 C35 -2.1(6) . . . . ? N12 C31 C36 C35 -174.9(4) . . . . ? C46 C41 C42 C43 0.6(6) . . . . ? N22 C41 C42 C43 177.9(4) . . . . ? C41 C42 C43 C44 0.2(7) . . . . ? C42 C43 C44 C45 -0.3(7) . . . . ? C42 C43 C44 C47 -179.2(4) . . . . ? C43 C44 C45 C46 -0.3(6) . . . . ? C47 C44 C45 C46 178.5(4) . . . . ? C44 C45 C46 C41 1.1(6) . . . . ? C42 C41 C46 C45 -1.3(6) . . . . ? N22 C41 C46 C45 -178.6(3) . . . . ? C21 C11 N11 C14 -173.7(3) . . . . ? C12 C11 N11 C14 2.6(4) . . . . ? C21 C11 N11 B1 14.0(5) . . . . ? C12 C11 N11 B1 -169.7(3) . . . . ? C15 C14 N11 C11 177.9(3) . . . . ? C13 C14 N11 C11 -2.4(4) . . . . ? C15 C14 N11 B1 -10.6(6) . . . . ? C13 C14 N11 B1 169.1(3) . . . . ? F2 B1 N11 C11 -148.2(3) . . . . ? F1 B1 N11 C11 91.3(4) . . . . ? N22 B1 N11 C11 -26.2(4) . . . . ? F2 B1 N11 C14 41.5(5) . . . . ? F1 B1 N11 C14 -79.1(4) . . . . ? N22 B1 N11 C14 163.5(3) . . . . ? C11 C12 N12 C31 178.5(3) . . . . ? C13 C12 N12 C31 -7.3(6) . . . . ? C36 C31 N12 C12 -57.5(5) . . . . ? C32 C31 N12 C12 129.6(4) . . . . ? C25 C24 N21 C21 179.0(3) . . . . ? C23 C24 N21 C21 0.2(4) . . . . ? C11 C21 N21 C24 -172.8(3) . . . . ? C22 C21 N21 C24 0.1(4) . . . . ? C21 C22 N22 C41 171.6(3) . . . . ? C23 C22 N22 C41 -8.8(6) . . . . ? C21 C22 N22 B1 -8.6(5) . . . . ? C23 C22 N22 B1 171.0(4) . . . . ? C42 C41 N22 C22 123.0(4) . . . . ? C46 C41 N22 C22 -59.8(5) . . . . ? C42 C41 N22 B1 -56.8(5) . . . . ? C46 C41 N22 B1 120.4(4) . . . . ? F2 B1 N22 C22 145.9(3) . . . . ? F1 B1 N22 C22 -94.9(4) . . . . ? N11 B1 N22 C22 23.3(4) . . . . ? F2 B1 N22 C41 -34.4(4) . . . . ? F1 B1 N22 C41 84.9(4) . . . . ? N11 B1 N22 C41 -156.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.08 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.537 _refine_diff_density_min -0.794 _refine_diff_density_rms 0.062 # Attachment '- 2c.cif' data_vic1109 _database_code_depnum_ccdc_archive 'CCDC 895626' #TrackingRef '- 2c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H27 B F2 N4' _chemical_formula_sum 'C32 H27 B F2 N4' _chemical_formula_weight 516.39 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.0332(8) _cell_length_b 14.8026(10) _cell_length_c 15.5572(10) _cell_angle_alpha 89.0111(8) _cell_angle_beta 83.5450(8) _cell_angle_gamma 72.8575(8) _cell_volume 2630.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4712 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 23.70 _exptl_crystal_description fragment _exptl_crystal_colour blue _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9489 _exptl_absorpt_correction_T_max 0.9818 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 20842 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 26.36 _reflns_number_total 10640 _reflns_number_gt 8041 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXD (Schneider & Sheldrick, 2002)' _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^)+(0.0588P)^2^+0.7130P] 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 10640 _refine_ls_number_parameters 711 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1217 _refine_ls_wR_factor_gt 0.1106 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 F1A F 0.07374(10) 0.20739(7) 0.30072(7) 0.0467(3) Uani 1 1 d . . . F2A F 0.21083(9) 0.08190(9) 0.34395(6) 0.0498(3) Uani 1 1 d . . . N11A N 0.01808(11) 0.06649(9) 0.33102(8) 0.0269(3) Uani 1 1 d . . . N12A N -0.14817(12) -0.09234(9) 0.31777(9) 0.0323(3) Uani 1 1 d . . . N21A N 0.01791(12) -0.09770(9) 0.15622(8) 0.0302(3) Uani 1 1 d . . . H21A H -0.0297 -0.1320 0.1704 0.036 Uiso 1 1 calc R . . N22A N 0.15652(11) 0.07486(8) 0.20032(8) 0.0254(3) Uani 1 1 d . . . C11A C -0.01229(13) -0.00152(10) 0.29034(10) 0.0266(3) Uani 1 1 d . . . C12A C -0.10743(13) -0.02795(10) 0.34432(10) 0.0273(3) Uani 1 1 d . . . C13A C -0.13187(13) 0.03376(11) 0.42117(10) 0.0272(3) Uani 1 1 d . . . C14A C -0.05488(13) 0.08952(11) 0.41006(9) 0.0273(3) Uani 1 1 d . . . C15A C -0.05628(15) 0.15679(12) 0.47029(10) 0.0334(4) Uani 1 1 d . . . H15A H -0.0045 0.1945 0.4619 0.040 Uiso 1 1 calc R . . C16A C -0.13616(15) 0.16758(12) 0.54392(11) 0.0374(4) Uani 1 1 d . . . H16A H -0.1395 0.2141 0.5862 0.045 Uiso 1 1 calc R . . C17A C -0.21108(15) 0.11201(12) 0.55708(11) 0.0366(4) Uani 1 1 d . . . H17A H -0.2638 0.1202 0.6086 0.044 Uiso 1 1 calc R . . C18A C -0.21004(14) 0.04471(11) 0.49604(10) 0.0318(4) Uani 1 1 d . . . H18A H -0.2616 0.0068 0.5051 0.038 Uiso 1 1 calc R . . C21A C 0.03822(13) -0.03176(10) 0.20879(10) 0.0259(3) Uani 1 1 d . . . C22A C 0.12088(13) 0.00872(10) 0.16307(9) 0.0245(3) Uani 1 1 d . . . C23A C 0.14891(13) -0.03515(11) 0.07848(10) 0.0277(3) Uani 1 1 d . . . C24A C 0.08406(13) -0.10107(11) 0.07828(10) 0.0282(3) Uani 1 1 d . . . C25A C 0.09129(15) -0.15811(12) 0.00678(11) 0.0368(4) Uani 1 1 d . . . H25A H 0.0487 -0.2030 0.0079 0.044 Uiso 1 1 calc R . . C26A C 0.16230(17) -0.14722(14) -0.06567(12) 0.0460(5) Uani 1 1 d . . . H26A H 0.1687 -0.1853 -0.1156 0.055 Uiso 1 1 calc R . . C27A C 0.22555(18) -0.08137(15) -0.06778(12) 0.0492(5) Uani 1 1 d . . . H27A H 0.2732 -0.0753 -0.1192 0.059 Uiso 1 1 calc R . . C28A C 0.22004(15) -0.02557(13) 0.00288(11) 0.0384(4) Uani 1 1 d . . . H28A H 0.2635 0.0188 0.0008 0.046 Uiso 1 1 calc R . . C31A C -0.24530(15) -0.11344(11) 0.36562(10) 0.0314(4) Uani 1 1 d . . . C32A C -0.35817(16) -0.05096(12) 0.36556(11) 0.0377(4) Uani 1 1 d . . . C33A C -0.45166(16) -0.07660(13) 0.40831(13) 0.0447(4) Uani 1 1 d . . . H33A H -0.5287 -0.0348 0.4086 0.054 Uiso 1 1 calc R . . C34A C -0.43498(18) -0.16123(14) 0.45015(13) 0.0505(5) Uani 1 1 d . . . H34A H -0.4997 -0.1770 0.4804 0.061 Uiso 1 1 calc R . . C35A C -0.32376(18) -0.22311(13) 0.44798(12) 0.0465(5) Uani 1 1 d . . . H35A H -0.3128 -0.2818 0.4765 0.056 Uiso 1 1 calc R . . C36A C -0.22697(15) -0.20168(12) 0.40495(11) 0.0348(4) Uani 1 1 d . . . C37A C -0.38071(18) 0.04173(14) 0.32002(14) 0.0517(5) Uani 1 1 d . . . H37A H -0.4645 0.0671 0.3144 0.062 Uiso 1 1 calc R . . H37B H -0.3364 0.0322 0.2624 0.062 Uiso 1 1 calc R . . H37C H -0.3560 0.0864 0.3535 0.062 Uiso 1 1 calc R . . C38A C -0.10711(16) -0.27171(13) 0.40018(13) 0.0447(4) Uani 1 1 d . . . H38A H -0.1141 -0.3344 0.4159 0.054 Uiso 1 1 calc R . . H38B H -0.0611 -0.2521 0.4404 0.054 Uiso 1 1 calc R . . H38C H -0.0680 -0.2743 0.3411 0.054 Uiso 1 1 calc R . . C41A C 0.24654(14) 0.10753(11) 0.15182(10) 0.0314(4) Uani 1 1 d . . . C42A C 0.21589(19) 0.19264(13) 0.10840(11) 0.0437(5) Uani 1 1 d . . . C43A C 0.3084(3) 0.21720(19) 0.05892(14) 0.0752(9) Uani 1 1 d . . . H43A H 0.2916 0.2746 0.0279 0.090 Uiso 1 1 calc R . . C44A C 0.4224(3) 0.1599(3) 0.05459(18) 0.0927(11) Uani 1 1 d . . . H44A H 0.4828 0.1776 0.0202 0.111 Uiso 1 1 calc R . . C45A C 0.4485(2) 0.0782(2) 0.09928(18) 0.0762(8) Uani 1 1 d . . . H45A H 0.5276 0.0400 0.0967 0.091 Uiso 1 1 calc R . . C46A C 0.36260(16) 0.04947(14) 0.14844(13) 0.0482(5) Uani 1 1 d . . . C47A C 0.0928(2) 0.25471(14) 0.11195(13) 0.0589(6) Uani 1 1 d . . . H47A H 0.0795 0.2841 0.0556 0.071 Uiso 1 1 calc R . . H47B H 0.0790 0.3040 0.1565 0.071 Uiso 1 1 calc R . . H47C H 0.0390 0.2168 0.1261 0.071 Uiso 1 1 calc R . . C48A C 0.39413(18) -0.04267(15) 0.19420(18) 0.0677(7) Uani 1 1 d . . . H48A H 0.4794 -0.0668 0.1931 0.081 Uiso 1 1 calc R . . H48B H 0.3656 -0.0883 0.1652 0.081 Uiso 1 1 calc R . . H48C H 0.3581 -0.0334 0.2543 0.081 Uiso 1 1 calc R . . B1A B 0.11618(16) 0.10890(13) 0.29583(12) 0.0301(4) Uani 1 1 d . . . F1B F -0.03220(9) 0.62526(8) 0.06794(6) 0.0455(3) Uani 1 1 d . . . F2B F -0.02929(8) 0.72437(6) 0.17457(7) 0.0448(3) Uani 1 1 d . . . N11B N -0.08337(10) 0.58423(8) 0.21393(8) 0.0257(3) Uani 1 1 d . . . N12B N -0.12351(11) 0.41051(9) 0.36157(8) 0.0279(3) Uani 1 1 d . . . N21B N 0.13114(11) 0.37934(9) 0.29752(8) 0.0268(3) Uani 1 1 d . . . H21B H 0.0981 0.3461 0.3338 0.032 Uiso 1 1 calc R . . N22B N 0.12348(11) 0.57441(9) 0.15998(8) 0.0255(3) Uani 1 1 d . . . C11B C -0.04352(13) 0.50533(10) 0.26061(9) 0.0242(3) Uani 1 1 d . . . C12B C -0.14231(13) 0.48051(10) 0.31005(10) 0.0252(3) Uani 1 1 d . . . C13B C -0.24677(13) 0.55263(11) 0.28574(10) 0.0278(3) Uani 1 1 d . . . C14B C -0.20652(13) 0.61408(11) 0.22922(10) 0.0273(3) Uani 1 1 d . . . C15B C -0.28240(14) 0.69215(12) 0.19565(11) 0.0361(4) Uani 1 1 d . . . H15B H -0.2546 0.7343 0.1585 0.043 Uiso 1 1 calc R . . C16B C -0.40101(16) 0.70618(14) 0.21855(13) 0.0467(5) Uani 1 1 d . . . H16B H -0.4556 0.7591 0.1964 0.056 Uiso 1 1 calc R . . C17B C -0.44230(15) 0.64519(14) 0.27282(13) 0.0480(5) Uani 1 1 d . . . H17B H -0.5243 0.6567 0.2865 0.058 Uiso 1 1 calc R . . C18B C -0.36623(14) 0.56798(13) 0.30744(11) 0.0378(4) Uani 1 1 d . . . H18B H -0.3947 0.5265 0.3450 0.045 Uiso 1 1 calc R . . C21B C 0.07376(13) 0.46088(10) 0.25745(10) 0.0248(3) Uani 1 1 d . . . C22B C 0.15708(13) 0.49639(10) 0.20663(9) 0.0245(3) Uani 1 1 d . . . C23B C 0.27020(13) 0.43154(10) 0.21726(10) 0.0264(3) Uani 1 1 d . . . C24B C 0.24857(13) 0.35908(10) 0.27112(10) 0.0264(3) Uani 1 1 d . . . C25B C 0.33823(14) 0.28020(11) 0.29073(11) 0.0323(4) Uani 1 1 d . . . H25B H 0.3227 0.2308 0.3253 0.039 Uiso 1 1 calc R . . C26B C 0.45027(15) 0.27706(13) 0.25764(12) 0.0399(4) Uani 1 1 d . . . H26B H 0.5134 0.2240 0.2696 0.048 Uiso 1 1 calc R . . C27B C 0.47411(15) 0.34966(13) 0.20692(12) 0.0424(4) Uani 1 1 d . . . H27B H 0.5530 0.3456 0.1867 0.051 Uiso 1 1 calc R . . C28B C 0.38627(14) 0.42631(12) 0.18590(11) 0.0353(4) Uani 1 1 d . . . H28B H 0.4032 0.4749 0.1509 0.042 Uiso 1 1 calc R . . C31B C -0.22205(13) 0.39198(11) 0.41004(10) 0.0277(3) Uani 1 1 d . . . C32B C -0.27508(14) 0.33078(11) 0.37515(10) 0.0308(3) Uani 1 1 d . . . C33B C -0.37029(15) 0.31366(13) 0.42418(12) 0.0390(4) Uani 1 1 d . . . H33B H -0.4082 0.2728 0.4017 0.047 Uiso 1 1 calc R . . C34B C -0.41079(16) 0.35475(13) 0.50493(12) 0.0419(4) Uani 1 1 d . . . H34B H -0.4770 0.3431 0.5370 0.050 Uiso 1 1 calc R . . C35B C -0.35531(15) 0.41276(12) 0.53916(11) 0.0390(4) Uani 1 1 d . . . H35B H -0.3834 0.4403 0.5951 0.047 Uiso 1 1 calc R . . C36B C -0.25888(14) 0.43160(11) 0.49310(11) 0.0325(4) Uani 1 1 d . . . C37B C -0.22975(15) 0.28606(13) 0.28712(11) 0.0404(4) Uani 1 1 d . . . H37D H -0.2683 0.2381 0.2769 0.048 Uiso 1 1 calc R . . H37E H -0.1451 0.2563 0.2842 0.048 Uiso 1 1 calc R . . H37F H -0.2463 0.3347 0.2429 0.048 Uiso 1 1 calc R . . C38B C -0.19644(18) 0.49287(14) 0.53138(13) 0.0490(5) Uani 1 1 d . . . H38D H -0.2332 0.5127 0.5902 0.059 Uiso 1 1 calc R . . H38E H -0.2014 0.5488 0.4956 0.059 Uiso 1 1 calc R . . H38F H -0.1141 0.4570 0.5332 0.059 Uiso 1 1 calc R . . C41B C 0.21377(13) 0.60500(10) 0.10924(10) 0.0266(3) Uani 1 1 d . . . C42B C 0.25384(15) 0.56731(12) 0.02592(11) 0.0343(4) Uani 1 1 d . . . C43B C 0.34451(17) 0.59486(14) -0.01952(12) 0.0454(5) Uani 1 1 d . . . H43B H 0.3745 0.5696 -0.0760 0.055 Uiso 1 1 calc R . . C44B C 0.39170(17) 0.65787(15) 0.01559(13) 0.0499(5) Uani 1 1 d . . . H44B H 0.4535 0.6758 -0.0166 0.060 Uiso 1 1 calc R . . C45B C 0.34930(16) 0.69517(13) 0.09763(12) 0.0425(4) Uani 1 1 d . . . H45B H 0.3816 0.7394 0.1210 0.051 Uiso 1 1 calc R . . C46B C 0.26007(14) 0.66911(11) 0.14670(10) 0.0308(3) Uani 1 1 d . . . C47B C 0.20601(19) 0.49686(14) -0.01398(13) 0.0504(5) Uani 1 1 d . . . H47D H 0.2618 0.4635 -0.0622 0.060 Uiso 1 1 calc R . . H47E H 0.1314 0.5300 -0.0354 0.060 Uiso 1 1 calc R . . H47F H 0.1937 0.4512 0.0296 0.060 Uiso 1 1 calc R . . C48B C 0.21987(15) 0.70542(13) 0.23788(11) 0.0394(4) Uani 1 1 d . . . H48D H 0.2547 0.7554 0.2496 0.047 Uiso 1 1 calc R . . H48E H 0.2443 0.6536 0.2782 0.047 Uiso 1 1 calc R . . H48F H 0.1344 0.7310 0.2454 0.047 Uiso 1 1 calc R . . B1B B -0.00698(16) 0.62924(12) 0.15225(12) 0.0292(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1A 0.0670(7) 0.0314(5) 0.0460(6) -0.0095(4) 0.0184(5) -0.0296(5) F2A 0.0497(6) 0.0824(8) 0.0334(5) 0.0111(5) -0.0111(5) -0.0423(6) N11A 0.0338(7) 0.0256(6) 0.0249(6) -0.0005(5) 0.0008(5) -0.0156(5) N12A 0.0388(8) 0.0304(7) 0.0323(7) -0.0004(6) 0.0048(6) -0.0202(6) N21A 0.0370(7) 0.0297(7) 0.0291(7) -0.0036(5) 0.0034(6) -0.0202(6) N22A 0.0278(7) 0.0240(6) 0.0274(7) 0.0009(5) 0.0006(5) -0.0139(5) C11A 0.0320(8) 0.0233(7) 0.0271(8) 0.0022(6) -0.0007(6) -0.0135(6) C12A 0.0320(8) 0.0252(8) 0.0268(8) 0.0034(6) 0.0005(6) -0.0135(6) C13A 0.0311(8) 0.0263(8) 0.0258(8) 0.0036(6) -0.0006(6) -0.0118(6) C14A 0.0312(8) 0.0287(8) 0.0225(7) 0.0022(6) -0.0002(6) -0.0110(6) C15A 0.0395(9) 0.0344(9) 0.0305(9) -0.0026(7) -0.0008(7) -0.0181(7) C16A 0.0461(10) 0.0375(9) 0.0288(9) -0.0063(7) 0.0006(7) -0.0140(8) C17A 0.0394(9) 0.0409(10) 0.0272(8) -0.0006(7) 0.0050(7) -0.0116(8) C18A 0.0340(9) 0.0344(9) 0.0282(8) 0.0033(7) 0.0015(7) -0.0137(7) C21A 0.0306(8) 0.0246(7) 0.0259(8) 0.0007(6) -0.0011(6) -0.0143(6) C22A 0.0257(7) 0.0222(7) 0.0266(8) 0.0024(6) -0.0021(6) -0.0091(6) C23A 0.0295(8) 0.0276(8) 0.0274(8) -0.0008(6) -0.0007(6) -0.0113(6) C24A 0.0298(8) 0.0282(8) 0.0283(8) -0.0005(6) -0.0009(6) -0.0118(6) C25A 0.0406(9) 0.0400(9) 0.0341(9) -0.0076(7) -0.0014(7) -0.0191(8) C26A 0.0530(11) 0.0575(12) 0.0315(9) -0.0151(8) 0.0034(8) -0.0246(10) C27A 0.0545(12) 0.0695(13) 0.0299(9) -0.0103(9) 0.0134(8) -0.0338(10) C28A 0.0411(10) 0.0469(10) 0.0321(9) -0.0032(8) 0.0053(7) -0.0238(8) C31A 0.0398(9) 0.0321(8) 0.0285(8) -0.0029(7) 0.0030(7) -0.0226(7) C32A 0.0429(10) 0.0340(9) 0.0399(10) 0.0001(7) 0.0000(8) -0.0189(8) C33A 0.0371(10) 0.0431(10) 0.0558(12) -0.0047(9) 0.0065(8) -0.0188(8) C34A 0.0476(11) 0.0512(12) 0.0580(12) -0.0004(10) 0.0162(9) -0.0307(10) C35A 0.0578(12) 0.0393(10) 0.0488(11) 0.0087(8) 0.0052(9) -0.0287(9) C36A 0.0437(10) 0.0328(9) 0.0333(9) -0.0007(7) 0.0004(7) -0.0212(8) C37A 0.0496(12) 0.0440(11) 0.0638(13) 0.0128(10) -0.0060(10) -0.0180(9) C38A 0.0487(11) 0.0371(10) 0.0527(11) 0.0029(8) -0.0054(9) -0.0196(8) C41A 0.0377(9) 0.0359(9) 0.0278(8) -0.0054(7) 0.0043(7) -0.0245(7) C42A 0.0790(14) 0.0404(10) 0.0247(8) 0.0008(7) -0.0031(9) -0.0388(10) C43A 0.144(3) 0.0733(16) 0.0374(11) -0.0011(11) 0.0117(14) -0.0839(19) C44A 0.107(2) 0.120(3) 0.0749(18) -0.0470(18) 0.0543(17) -0.091(2) C45A 0.0531(14) 0.0943(19) 0.0930(19) -0.0475(16) 0.0331(13) -0.0523(14) C46A 0.0363(10) 0.0532(12) 0.0591(12) -0.0245(10) 0.0094(9) -0.0234(9) C47A 0.1040(19) 0.0368(10) 0.0460(12) 0.0131(9) -0.0389(12) -0.0261(11) C48A 0.0405(11) 0.0467(12) 0.111(2) -0.0197(13) -0.0183(12) -0.0010(10) B1A 0.0379(10) 0.0313(9) 0.0273(9) 0.0000(7) 0.0010(8) -0.0216(8) F1B 0.0395(6) 0.0671(7) 0.0337(5) 0.0190(5) -0.0095(4) -0.0205(5) F2B 0.0332(5) 0.0239(5) 0.0789(8) 0.0076(5) -0.0024(5) -0.0126(4) N11B 0.0248(6) 0.0249(6) 0.0295(7) 0.0036(5) -0.0038(5) -0.0103(5) N12B 0.0272(7) 0.0274(7) 0.0313(7) 0.0031(5) 0.0001(5) -0.0126(5) N21B 0.0265(7) 0.0253(6) 0.0309(7) 0.0064(5) -0.0023(5) -0.0118(5) N22B 0.0272(7) 0.0255(6) 0.0267(7) 0.0045(5) -0.0008(5) -0.0132(5) C11B 0.0279(8) 0.0225(7) 0.0254(7) 0.0008(6) -0.0021(6) -0.0126(6) C12B 0.0259(8) 0.0249(7) 0.0272(8) -0.0010(6) -0.0017(6) -0.0117(6) C13B 0.0258(8) 0.0289(8) 0.0293(8) 0.0004(6) -0.0015(6) -0.0096(6) C14B 0.0260(8) 0.0284(8) 0.0293(8) 0.0000(6) -0.0022(6) -0.0110(6) C15B 0.0343(9) 0.0333(9) 0.0422(10) 0.0104(7) -0.0076(7) -0.0115(7) C16B 0.0314(9) 0.0442(11) 0.0617(12) 0.0166(9) -0.0103(9) -0.0060(8) C17B 0.0243(9) 0.0521(11) 0.0634(13) 0.0146(10) -0.0024(8) -0.0067(8) C18B 0.0273(8) 0.0427(10) 0.0434(10) 0.0092(8) -0.0003(7) -0.0120(7) C21B 0.0274(8) 0.0222(7) 0.0274(8) 0.0020(6) -0.0025(6) -0.0115(6) C22B 0.0270(8) 0.0239(7) 0.0252(7) -0.0011(6) -0.0022(6) -0.0114(6) C23B 0.0274(8) 0.0263(8) 0.0271(8) 0.0004(6) -0.0025(6) -0.0107(6) C24B 0.0282(8) 0.0269(8) 0.0267(8) -0.0001(6) -0.0032(6) -0.0119(6) C25B 0.0335(9) 0.0282(8) 0.0362(9) 0.0067(7) -0.0071(7) -0.0100(7) C26B 0.0307(9) 0.0389(10) 0.0466(10) 0.0090(8) -0.0075(8) -0.0045(7) C27B 0.0245(8) 0.0501(11) 0.0496(11) 0.0112(9) 0.0007(7) -0.0087(8) C28B 0.0286(8) 0.0397(9) 0.0385(9) 0.0089(7) -0.0013(7) -0.0128(7) C31B 0.0265(8) 0.0271(8) 0.0303(8) 0.0064(6) -0.0010(6) -0.0103(6) C32B 0.0289(8) 0.0334(8) 0.0323(8) 0.0035(7) -0.0015(7) -0.0134(7) C33B 0.0361(9) 0.0441(10) 0.0432(10) 0.0005(8) 0.0002(8) -0.0233(8) C34B 0.0371(9) 0.0478(11) 0.0430(10) 0.0023(8) 0.0087(8) -0.0208(8) C35B 0.0427(10) 0.0377(9) 0.0342(9) -0.0001(7) 0.0094(8) -0.0132(8) C36B 0.0374(9) 0.0287(8) 0.0327(9) 0.0028(7) -0.0005(7) -0.0132(7) C37B 0.0378(10) 0.0510(11) 0.0374(10) -0.0060(8) -0.0001(8) -0.0221(8) C38B 0.0611(13) 0.0489(11) 0.0441(11) -0.0091(9) 0.0044(9) -0.0302(10) C41B 0.0265(8) 0.0252(8) 0.0300(8) 0.0059(6) -0.0012(6) -0.0114(6) C42B 0.0396(9) 0.0325(9) 0.0326(9) 0.0017(7) 0.0016(7) -0.0156(7) C43B 0.0490(11) 0.0496(11) 0.0379(10) 0.0008(8) 0.0120(8) -0.0210(9) C44B 0.0440(11) 0.0600(13) 0.0515(12) 0.0053(10) 0.0108(9) -0.0303(10) C45B 0.0403(10) 0.0461(10) 0.0510(11) 0.0036(9) -0.0032(8) -0.0288(9) C46B 0.0291(8) 0.0320(8) 0.0340(9) 0.0038(7) -0.0057(7) -0.0127(7) C47B 0.0664(13) 0.0483(11) 0.0418(11) -0.0127(9) 0.0075(9) -0.0294(10) C48B 0.0385(10) 0.0446(10) 0.0400(10) -0.0031(8) -0.0077(8) -0.0184(8) B1B 0.0284(9) 0.0271(9) 0.0348(10) 0.0071(7) -0.0040(7) -0.0126(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1A B1A 1.396(2) . ? F2A B1A 1.389(2) . ? N11A C11A 1.3558(19) . ? N11A C14A 1.4122(19) . ? N11A B1A 1.539(2) . ? N12A C12A 1.2859(19) . ? N12A C31A 1.4245(19) . ? N21A C24A 1.3668(19) . ? N21A C21A 1.3765(19) . ? N22A C22A 1.3421(18) . ? N22A C41A 1.4454(18) . ? N22A B1A 1.555(2) . ? C11A C21A 1.366(2) . ? C11A C12A 1.485(2) . ? C12A C13A 1.466(2) . ? C13A C18A 1.392(2) . ? C13A C14A 1.407(2) . ? C14A C15A 1.374(2) . ? C15A C16A 1.389(2) . ? C16A C17A 1.386(2) . ? C17A C18A 1.385(2) . ? C21A C22A 1.425(2) . ? C22A C23A 1.438(2) . ? C23A C28A 1.406(2) . ? C23A C24A 1.418(2) . ? C24A C25A 1.388(2) . ? C25A C26A 1.373(2) . ? C26A C27A 1.400(3) . ? C27A C28A 1.370(2) . ? C31A C32A 1.400(2) . ? C31A C36A 1.401(2) . ? C32A C33A 1.388(2) . ? C32A C37A 1.499(2) . ? C33A C34A 1.373(3) . ? C34A C35A 1.378(3) . ? C35A C36A 1.393(2) . ? C36A C38A 1.503(3) . ? C41A C42A 1.390(2) . ? C41A C46A 1.403(3) . ? C42A C43A 1.414(3) . ? C42A C47A 1.491(3) . ? C43A C44A 1.379(4) . ? C44A C45A 1.356(4) . ? C45A C46A 1.380(3) . ? C46A C48A 1.494(3) . ? F1B B1B 1.385(2) . ? F2B B1B 1.396(2) . ? N11B C11B 1.3566(18) . ? N11B C14B 1.4093(19) . ? N11B B1B 1.533(2) . ? N12B C12B 1.2811(19) . ? N12B C31B 1.4259(18) . ? N21B C24B 1.3709(19) . ? N21B C21B 1.3790(19) . ? N22B C22B 1.3363(19) . ? N22B C41B 1.4468(18) . ? N22B B1B 1.557(2) . ? C11B C21B 1.366(2) . ? C11B C12B 1.477(2) . ? C12B C13B 1.471(2) . ? C13B C18B 1.390(2) . ? C13B C14B 1.404(2) . ? C14B C15B 1.381(2) . ? C15B C16B 1.386(2) . ? C16B C17B 1.385(3) . ? C17B C18B 1.381(2) . ? C21B C22B 1.423(2) . ? C22B C23B 1.441(2) . ? C23B C28B 1.407(2) . ? C23B C24B 1.416(2) . ? C24B C25B 1.393(2) . ? C25B C26B 1.376(2) . ? C26B C27B 1.400(2) . ? C27B C28B 1.367(2) . ? C31B C36B 1.398(2) . ? C31B C32B 1.399(2) . ? C32B C33B 1.388(2) . ? C32B C37B 1.504(2) . ? C33B C34B 1.378(2) . ? C34B C35B 1.379(2) . ? C35B C36B 1.391(2) . ? C36B C38B 1.504(2) . ? C41B C42B 1.396(2) . ? C41B C46B 1.398(2) . ? C42B C43B 1.391(2) . ? C42B C47B 1.503(2) . ? C43B C44B 1.375(3) . ? C44B C45B 1.381(3) . ? C45B C46B 1.391(2) . ? C46B C48B 1.501(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11A N11A C14A 107.95(12) . . ? C11A N11A B1A 124.90(13) . . ? C14A N11A B1A 127.15(12) . . ? C12A N12A C31A 120.86(13) . . ? C24A N21A C21A 108.65(12) . . ? C22A N22A C41A 117.67(12) . . ? C22A N22A B1A 123.12(12) . . ? C41A N22A B1A 118.84(12) . . ? N11A C11A C21A 120.33(13) . . ? N11A C11A C12A 110.32(13) . . ? C21A C11A C12A 129.22(14) . . ? N12A C12A C13A 135.63(14) . . ? N12A C12A C11A 120.22(13) . . ? C13A C12A C11A 104.15(12) . . ? C18A C13A C14A 119.62(14) . . ? C18A C13A C12A 133.55(14) . . ? C14A C13A C12A 106.83(13) . . ? C15A C14A C13A 121.86(14) . . ? C15A C14A N11A 127.41(14) . . ? C13A C14A N11A 110.73(13) . . ? C14A C15A C16A 117.60(15) . . ? C17A C16A C15A 121.51(16) . . ? C18A C17A C16A 120.78(15) . . ? C17A C18A C13A 118.61(15) . . ? C11A C21A N21A 129.27(14) . . ? C11A C21A C22A 121.49(13) . . ? N21A C21A C22A 109.16(13) . . ? N22A C22A C21A 121.10(13) . . ? N22A C22A C23A 132.70(13) . . ? C21A C22A C23A 106.20(12) . . ? C28A C23A C24A 118.76(14) . . ? C28A C23A C22A 135.17(14) . . ? C24A C23A C22A 106.07(13) . . ? N21A C24A C25A 128.01(14) . . ? N21A C24A C23A 109.90(13) . . ? C25A C24A C23A 122.08(14) . . ? C26A C25A C24A 117.48(16) . . ? C25A C26A C27A 121.60(16) . . ? C28A C27A C26A 121.31(16) . . ? C27A C28A C23A 118.75(16) . . ? C32A C31A C36A 120.96(15) . . ? C32A C31A N12A 120.18(14) . . ? C36A C31A N12A 118.54(15) . . ? C33A C32A C31A 118.62(16) . . ? C33A C32A C37A 119.40(17) . . ? C31A C32A C37A 121.98(15) . . ? C34A C33A C32A 121.27(18) . . ? C33A C34A C35A 119.54(17) . . ? C34A C35A C36A 121.63(17) . . ? C35A C36A C31A 117.90(16) . . ? C35A C36A C38A 120.84(16) . . ? C31A C36A C38A 121.26(15) . . ? C42A C41A C46A 122.40(16) . . ? C42A C41A N22A 119.72(16) . . ? C46A C41A N22A 117.85(15) . . ? C41A C42A C43A 116.2(2) . . ? C41A C42A C47A 122.63(16) . . ? C43A C42A C47A 121.2(2) . . ? C44A C43A C42A 121.6(2) . . ? C45A C44A C43A 120.1(2) . . ? C44A C45A C46A 121.4(2) . . ? C45A C46A C41A 118.2(2) . . ? C45A C46A C48A 119.9(2) . . ? C41A C46A C48A 121.87(17) . . ? F2A B1A F1A 107.18(13) . . ? F2A B1A N11A 111.88(13) . . ? F1A B1A N11A 109.37(14) . . ? F2A B1A N22A 109.76(14) . . ? F1A B1A N22A 110.49(13) . . ? N11A B1A N22A 108.18(12) . . ? C11B N11B C14B 107.93(12) . . ? C11B N11B B1B 125.43(12) . . ? C14B N11B B1B 126.58(12) . . ? C12B N12B C31B 118.05(13) . . ? C24B N21B C21B 108.20(12) . . ? C22B N22B C41B 117.68(12) . . ? C22B N22B B1B 123.51(12) . . ? C41B N22B B1B 118.65(12) . . ? N11B C11B C21B 120.34(13) . . ? N11B C11B C12B 110.43(12) . . ? C21B C11B C12B 129.23(13) . . ? N12B C12B C13B 135.31(14) . . ? N12B C12B C11B 120.50(13) . . ? C13B C12B C11B 104.16(12) . . ? C18B C13B C14B 120.04(15) . . ? C18B C13B C12B 133.32(14) . . ? C14B C13B C12B 106.64(13) . . ? C15B C14B C13B 121.89(14) . . ? C15B C14B N11B 127.30(14) . . ? C13B C14B N11B 110.81(13) . . ? C14B C15B C16B 116.96(15) . . ? C17B C16B C15B 121.88(17) . . ? C18B C17B C16B 121.08(16) . . ? C17B C18B C13B 118.12(16) . . ? C11B C21B N21B 129.23(13) . . ? C11B C21B C22B 121.31(13) . . ? N21B C21B C22B 109.46(12) . . ? N22B C22B C21B 121.23(13) . . ? N22B C22B C23B 132.64(13) . . ? C21B C22B C23B 106.11(12) . . ? C28B C23B C24B 119.17(14) . . ? C28B C23B C22B 134.77(14) . . ? C24B C23B C22B 106.04(13) . . ? N21B C24B C25B 127.91(14) . . ? N21B C24B C23B 110.05(13) . . ? C25B C24B C23B 122.04(14) . . ? C26B C25B C24B 116.90(15) . . ? C25B C26B C27B 122.00(16) . . ? C28B C27B C26B 121.38(16) . . ? C27B C28B C23B 118.43(15) . . ? C36B C31B C32B 121.88(14) . . ? C36B C31B N12B 118.84(14) . . ? C32B C31B N12B 119.19(14) . . ? C33B C32B C31B 117.80(15) . . ? C33B C32B C37B 121.74(15) . . ? C31B C32B C37B 120.45(14) . . ? C34B C33B C32B 121.24(16) . . ? C33B C34B C35B 120.06(16) . . ? C34B C35B C36B 121.04(16) . . ? C35B C36B C31B 117.88(15) . . ? C35B C36B C38B 121.04(15) . . ? C31B C36B C38B 121.08(15) . . ? C42B C41B C46B 122.52(14) . . ? C42B C41B N22B 118.91(13) . . ? C46B C41B N22B 118.55(13) . . ? C43B C42B C41B 117.39(15) . . ? C43B C42B C47B 119.85(16) . . ? C41B C42B C47B 122.72(15) . . ? C44B C43B C42B 121.40(17) . . ? C43B C44B C45B 120.05(16) . . ? C44B C45B C46B 121.15(16) . . ? C45B C46B C41B 117.48(15) . . ? C45B C46B C48B 120.66(15) . . ? C41B C46B C48B 121.80(14) . . ? F1B B1B F2B 107.53(13) . . ? F1B B1B N11B 110.62(13) . . ? F2B B1B N11B 110.02(13) . . ? F1B B1B N22B 110.58(14) . . ? F2B B1B N22B 110.21(13) . . ? N11B B1B N22B 107.89(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14A N11A C11A C21A 174.72(14) . . . . ? B1A N11A C11A C21A -5.8(2) . . . . ? C14A N11A C11A C12A -1.50(17) . . . . ? B1A N11A C11A C12A 177.94(14) . . . . ? C31A N12A C12A C13A 4.3(3) . . . . ? C31A N12A C12A C11A -175.18(14) . . . . ? N11A C11A C12A N12A -179.21(14) . . . . ? C21A C11A C12A N12A 5.0(3) . . . . ? N11A C11A C12A C13A 1.14(17) . . . . ? C21A C11A C12A C13A -174.64(16) . . . . ? N12A C12A C13A C18A 0.7(3) . . . . ? C11A C12A C13A C18A -179.79(17) . . . . ? N12A C12A C13A C14A -179.89(18) . . . . ? C11A C12A C13A C14A -0.33(16) . . . . ? C18A C13A C14A C15A -1.7(2) . . . . ? C12A C13A C14A C15A 178.79(15) . . . . ? C18A C13A C14A N11A 178.99(14) . . . . ? C12A C13A C14A N11A -0.55(17) . . . . ? C11A N11A C14A C15A -178.00(16) . . . . ? B1A N11A C14A C15A 2.6(3) . . . . ? C11A N11A C14A C13A 1.30(17) . . . . ? B1A N11A C14A C13A -178.13(14) . . . . ? C13A C14A C15A C16A 0.7(2) . . . . ? N11A C14A C15A C16A 179.91(15) . . . . ? C14A C15A C16A C17A 0.7(3) . . . . ? C15A C16A C17A C18A -1.2(3) . . . . ? C16A C17A C18A C13A 0.2(2) . . . . ? C14A C13A C18A C17A 1.2(2) . . . . ? C12A C13A C18A C17A -179.41(16) . . . . ? N11A C11A C21A N21A -178.44(14) . . . . ? C12A C11A C21A N21A -3.0(3) . . . . ? N11A C11A C21A C22A -2.0(2) . . . . ? C12A C11A C21A C22A 173.42(14) . . . . ? C24A N21A C21A C11A 176.61(16) . . . . ? C24A N21A C21A C22A -0.18(17) . . . . ? C41A N22A C22A C21A 175.76(14) . . . . ? B1A N22A C22A C21A 2.9(2) . . . . ? C41A N22A C22A C23A -4.8(2) . . . . ? B1A N22A C22A C23A -177.68(16) . . . . ? C11A C21A C22A N22A 3.4(2) . . . . ? N21A C21A C22A N22A -179.50(13) . . . . ? C11A C21A C22A C23A -176.14(14) . . . . ? N21A C21A C22A C23A 0.95(17) . . . . ? N22A C22A C23A C28A -1.7(3) . . . . ? C21A C22A C23A C28A 177.80(18) . . . . ? N22A C22A C23A C24A 179.21(16) . . . . ? C21A C22A C23A C24A -1.31(17) . . . . ? C21A N21A C24A C25A 179.40(16) . . . . ? C21A N21A C24A C23A -0.69(18) . . . . ? C28A C23A C24A N21A -178.03(14) . . . . ? C22A C23A C24A N21A 1.26(18) . . . . ? C28A C23A C24A C25A 1.9(2) . . . . ? C22A C23A C24A C25A -178.83(15) . . . . ? N21A C24A C25A C26A 178.48(17) . . . . ? C23A C24A C25A C26A -1.4(3) . . . . ? C24A C25A C26A C27A 0.2(3) . . . . ? C25A C26A C27A C28A 0.6(3) . . . . ? C26A C27A C28A C23A -0.2(3) . . . . ? C24A C23A C28A C27A -1.0(3) . . . . ? C22A C23A C28A C27A 179.93(19) . . . . ? C12A N12A C31A C32A 73.7(2) . . . . ? C12A N12A C31A C36A -112.72(18) . . . . ? C36A C31A C32A C33A 2.5(3) . . . . ? N12A C31A C32A C33A 175.93(15) . . . . ? C36A C31A C32A C37A -176.81(17) . . . . ? N12A C31A C32A C37A -3.4(3) . . . . ? C31A C32A C33A C34A 0.1(3) . . . . ? C37A C32A C33A C34A 179.40(19) . . . . ? C32A C33A C34A C35A -1.6(3) . . . . ? C33A C34A C35A C36A 0.6(3) . . . . ? C34A C35A C36A C31A 1.9(3) . . . . ? C34A C35A C36A C38A -177.45(18) . . . . ? C32A C31A C36A C35A -3.4(2) . . . . ? N12A C31A C36A C35A -176.96(15) . . . . ? C32A C31A C36A C38A 175.88(16) . . . . ? N12A C31A C36A C38A 2.3(2) . . . . ? C22A N22A C41A C42A 100.10(17) . . . . ? B1A N22A C41A C42A -86.74(18) . . . . ? C22A N22A C41A C46A -77.95(19) . . . . ? B1A N22A C41A C46A 95.22(18) . . . . ? C46A C41A C42A C43A 1.0(3) . . . . ? N22A C41A C42A C43A -176.90(15) . . . . ? C46A C41A C42A C47A -179.84(16) . . . . ? N22A C41A C42A C47A 2.2(2) . . . . ? C41A C42A C43A C44A -0.3(3) . . . . ? C47A C42A C43A C44A -179.4(2) . . . . ? C42A C43A C44A C45A -0.9(4) . . . . ? C43A C44A C45A C46A 1.3(4) . . . . ? C44A C45A C46A C41A -0.5(3) . . . . ? C44A C45A C46A C48A 177.8(2) . . . . ? C42A C41A C46A C45A -0.7(3) . . . . ? N22A C41A C46A C45A 177.32(16) . . . . ? C42A C41A C46A C48A -178.94(17) . . . . ? N22A C41A C46A C48A -1.0(3) . . . . ? C11A N11A B1A F2A -110.47(17) . . . . ? C14A N11A B1A F2A 68.9(2) . . . . ? C11A N11A B1A F1A 130.95(15) . . . . ? C14A N11A B1A F1A -49.7(2) . . . . ? C11A N11A B1A N22A 10.5(2) . . . . ? C14A N11A B1A N22A -170.12(13) . . . . ? C22A N22A B1A F2A 113.40(15) . . . . ? C41A N22A B1A F2A -59.37(18) . . . . ? C22A N22A B1A F1A -128.61(14) . . . . ? C41A N22A B1A F1A 58.62(19) . . . . ? C22A N22A B1A N11A -8.9(2) . . . . ? C41A N22A B1A N11A 178.31(13) . . . . ? C14B N11B C11B C21B 179.67(14) . . . . ? B1B N11B C11B C21B 2.4(2) . . . . ? C14B N11B C11B C12B -0.42(16) . . . . ? B1B N11B C11B C12B -177.69(13) . . . . ? C31B N12B C12B C13B 0.1(3) . . . . ? C31B N12B C12B C11B 177.71(13) . . . . ? N11B C11B C12B N12B -176.85(13) . . . . ? C21B C11B C12B N12B 3.1(2) . . . . ? N11B C11B C12B C13B 1.43(16) . . . . ? C21B C11B C12B C13B -178.67(15) . . . . ? N12B C12B C13B C18B -4.0(3) . . . . ? C11B C12B C13B C18B 178.11(18) . . . . ? N12B C12B C13B C14B 176.03(17) . . . . ? C11B C12B C13B C14B -1.87(16) . . . . ? C18B C13B C14B C15B 1.9(2) . . . . ? C12B C13B C14B C15B -178.14(15) . . . . ? C18B C13B C14B N11B -178.24(14) . . . . ? C12B C13B C14B N11B 1.74(17) . . . . ? C11B N11B C14B C15B 179.03(16) . . . . ? B1B N11B C14B C15B -3.7(3) . . . . ? C11B N11B C14B C13B -0.85(17) . . . . ? B1B N11B C14B C13B 176.38(14) . . . . ? C13B C14B C15B C16B -1.5(3) . . . . ? N11B C14B C15B C16B 178.59(16) . . . . ? C14B C15B C16B C17B 0.2(3) . . . . ? C15B C16B C17B C18B 0.8(3) . . . . ? C16B C17B C18B C13B -0.5(3) . . . . ? C14B C13B C18B C17B -0.8(3) . . . . ? C12B C13B C18B C17B 179.24(17) . . . . ? N11B C11B C21B N21B -177.93(14) . . . . ? C12B C11B C21B N21B 2.2(3) . . . . ? N11B C11B C21B C22B 1.0(2) . . . . ? C12B C11B C21B C22B -178.94(14) . . . . ? C24B N21B C21B C11B 176.46(15) . . . . ? C24B N21B C21B C22B -2.53(16) . . . . ? C41B N22B C22B C21B -179.22(13) . . . . ? B1B N22B C22B C21B -3.8(2) . . . . ? C41B N22B C22B C23B -1.0(2) . . . . ? B1B N22B C22B C23B 174.41(15) . . . . ? C11B C21B C22B N22B -0.2(2) . . . . ? N21B C21B C22B N22B 178.90(13) . . . . ? C11B C21B C22B C23B -178.85(14) . . . . ? N21B C21B C22B C23B 0.24(16) . . . . ? N22B C22B C23B C28B 2.2(3) . . . . ? C21B C22B C23B C28B -179.34(18) . . . . ? N22B C22B C23B C24B -176.40(15) . . . . ? C21B C22B C23B C24B 2.05(16) . . . . ? C21B N21B C24B C25B -175.41(15) . . . . ? C21B N21B C24B C23B 3.90(17) . . . . ? C28B C23B C24B N21B 177.44(14) . . . . ? C22B C23B C24B N21B -3.69(17) . . . . ? C28B C23B C24B C25B -3.2(2) . . . . ? C22B C23B C24B C25B 175.67(14) . . . . ? N21B C24B C25B C26B -178.63(15) . . . . ? C23B C24B C25B C26B 2.1(2) . . . . ? C24B C25B C26B C27B 0.3(3) . . . . ? C25B C26B C27B C28B -1.8(3) . . . . ? C26B C27B C28B C23B 0.7(3) . . . . ? C24B C23B C28B C27B 1.7(2) . . . . ? C22B C23B C28B C27B -176.76(17) . . . . ? C12B N12B C31B C36B -93.06(18) . . . . ? C12B N12B C31B C32B 90.35(18) . . . . ? C36B C31B C32B C33B 3.1(2) . . . . ? N12B C31B C32B C33B 179.54(14) . . . . ? C36B C31B C32B C37B -177.27(15) . . . . ? N12B C31B C32B C37B -0.8(2) . . . . ? C31B C32B C33B C34B -0.6(3) . . . . ? C37B C32B C33B C34B 179.74(17) . . . . ? C32B C33B C34B C35B -1.2(3) . . . . ? C33B C34B C35B C36B 0.6(3) . . . . ? C34B C35B C36B C31B 1.8(3) . . . . ? C34B C35B C36B C38B -178.41(17) . . . . ? C32B C31B C36B C35B -3.6(2) . . . . ? N12B C31B C36B C35B 179.88(14) . . . . ? C32B C31B C36B C38B 176.53(16) . . . . ? N12B C31B C36B C38B 0.0(2) . . . . ? C22B N22B C41B C42B 86.59(18) . . . . ? B1B N22B C41B C42B -89.01(18) . . . . ? C22B N22B C41B C46B -91.48(17) . . . . ? B1B N22B C41B C46B 92.92(17) . . . . ? C46B C41B C42B C43B 0.9(2) . . . . ? N22B C41B C42B C43B -177.04(15) . . . . ? C46B C41B C42B C47B 178.74(16) . . . . ? N22B C41B C42B C47B 0.8(2) . . . . ? C41B C42B C43B C44B -1.0(3) . . . . ? C47B C42B C43B C44B -178.86(19) . . . . ? C42B C43B C44B C45B 0.1(3) . . . . ? C43B C44B C45B C46B 1.0(3) . . . . ? C44B C45B C46B C41B -1.0(3) . . . . ? C44B C45B C46B C48B 176.13(18) . . . . ? C42B C41B C46B C45B 0.0(2) . . . . ? N22B C41B C46B C45B 178.04(14) . . . . ? C42B C41B C46B C48B -177.07(15) . . . . ? N22B C41B C46B C48B 0.9(2) . . . . ? C11B N11B B1B F1B 115.61(16) . . . . ? C14B N11B B1B F1B -61.2(2) . . . . ? C11B N11B B1B F2B -125.72(15) . . . . ? C14B N11B B1B F2B 57.5(2) . . . . ? C11B N11B B1B N22B -5.5(2) . . . . ? C14B N11B B1B N22B 177.77(13) . . . . ? C22B N22B B1B F1B -114.98(15) . . . . ? C41B N22B B1B F1B 60.35(17) . . . . ? C22B N22B B1B F2B 126.26(15) . . . . ? C41B N22B B1B F2B -58.41(18) . . . . ? C22B N22B B1B N11B 6.1(2) . . . . ? C41B N22B B1B N11B -178.55(12) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.237 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.039 # Attachment '- 2d.cif' data_vic1003 _database_code_depnum_ccdc_archive 'CCDC 895627' #TrackingRef '- 2d.cif' _vrf_REFLT03_vic1003 ; RESPONSE: The crystal used for data collection was found to display non-merohedral twinning. Both components of the twin were indexed with the program CELL_NOW (Bruker AXS Inc., Madison, WI, 2004). The second twin component can be related to the first component by 180 deg rotation about the [1 3/4 -1/4] axis in real space and about the [1 1 0] axis in reciprocal space. Integrated intensities for the reflections from the two components were written into a SHELXL-97 HKLF 5 reflection file with the data integration program SAINT (version 7.68A), using all reflection data (exactly overlapped, partially overlapped and non-overlapped). The refined value of the twin fraction (SHELXL-97 BASF parameter) was 0.4506(6). ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H43 B F2 N4' _chemical_formula_sum 'C40 H43 B F2 N4' _chemical_formula_weight 628.59 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.7533(7) _cell_length_b 13.3999(8) _cell_length_c 24.5025(15) _cell_angle_alpha 91.7881(8) _cell_angle_beta 95.0164(8) _cell_angle_gamma 100.2580(8) _cell_volume 3457.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4683 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 25.52 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9601 _exptl_absorpt_correction_T_max 0.9882 _exptl_absorpt_process_details 'TWINABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 23870 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0459 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.75 _reflns_number_total 23870 _reflns_number_gt 16611 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXD (Schneider & Sheldrick, 2002)' _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^)+(0.0699P)^2^+1.1482P] 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 23870 _refine_ls_number_parameters 848 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0957 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1575 _refine_ls_wR_factor_gt 0.1359 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 F1A F 0.27140(10) 0.31625(8) 0.32809(4) 0.0359(3) Uani 1 1 d . . . F2A F 0.23071(11) 0.43550(8) 0.26983(5) 0.0393(3) Uani 1 1 d . . . N11A N 0.13125(14) 0.26191(10) 0.24597(6) 0.0252(3) Uani 1 1 d . . . N12A N -0.10999(14) 0.08852(11) 0.16925(6) 0.0273(3) Uani 1 1 d . . . N21A N -0.21327(14) 0.19691(11) 0.25891(6) 0.0280(4) Uani 1 1 d . . . H21A H -0.2530 0.1519 0.2334 0.034 Uiso 1 1 calc R . . N22A N 0.06119(13) 0.35947(10) 0.32296(6) 0.0240(3) Uani 1 1 d . . . C11A C 0.00906(16) 0.21403(12) 0.23430(7) 0.0239(4) Uani 1 1 d . . . C12A C -0.00229(17) 0.14252(13) 0.18629(7) 0.0250(4) Uani 1 1 d . . . C13A C 0.12786(17) 0.15391(13) 0.16973(7) 0.0267(4) Uani 1 1 d . . . C14A C 0.20502(17) 0.22589(13) 0.20708(7) 0.0271(4) Uani 1 1 d . . . C15A C 0.33403(19) 0.25382(15) 0.20367(8) 0.0331(5) Uani 1 1 d . . . H15A H 0.3853 0.3029 0.2288 0.040 Uiso 1 1 calc R . . C16A C 0.38559(19) 0.20683(16) 0.16183(9) 0.0397(5) Uani 1 1 d . . . H16A H 0.4741 0.2241 0.1586 0.048 Uiso 1 1 calc R . . C17A C 0.3111(2) 0.13521(16) 0.12463(9) 0.0394(5) Uani 1 1 d . . . H17A H 0.3493 0.1043 0.0966 0.047 Uiso 1 1 calc R . . C18A C 0.18183(19) 0.10868(14) 0.12811(8) 0.0329(4) Uani 1 1 d . . . H18A H 0.1307 0.0604 0.1025 0.040 Uiso 1 1 calc R . . C21A C -0.08459(17) 0.23574(12) 0.26473(7) 0.0245(4) Uani 1 1 d . . . C22A C -0.05671(16) 0.30870(12) 0.30959(7) 0.0237(4) Uani 1 1 d . . . C23A C -0.17547(16) 0.31184(13) 0.33236(7) 0.0252(4) Uani 1 1 d . . . C24A C -0.26865(17) 0.24056(13) 0.29976(8) 0.0274(4) Uani 1 1 d . . . C25A C -0.39571(18) 0.22437(15) 0.30974(9) 0.0342(5) Uani 1 1 d . . . H25A H -0.4572 0.1761 0.2881 0.041 Uiso 1 1 calc R . . C26A C -0.42924(19) 0.28066(15) 0.35203(9) 0.0395(5) Uani 1 1 d . . . H26A H -0.5158 0.2712 0.3593 0.047 Uiso 1 1 calc R . . C27A C -0.34002(19) 0.35142(15) 0.38463(9) 0.0372(5) Uani 1 1 d . . . H27A H -0.3670 0.3890 0.4135 0.045 Uiso 1 1 calc R . . C28A C -0.21320(17) 0.36749(14) 0.37555(8) 0.0307(4) Uani 1 1 d . . . H28A H -0.1527 0.4152 0.3980 0.037 Uiso 1 1 calc R . . C31A C -0.12093(17) 0.02269(13) 0.12157(8) 0.0280(4) Uani 1 1 d . . . C32A C -0.11898(19) -0.08089(14) 0.12851(8) 0.0342(5) Uani 1 1 d . . . C33A C -0.1346(2) -0.14426(16) 0.08148(9) 0.0428(5) Uani 1 1 d . . . H33A H -0.1320 -0.2143 0.0849 0.051 Uiso 1 1 calc R . . C34A C -0.1537(2) -0.10810(17) 0.03007(9) 0.0434(5) Uani 1 1 d . . . H34A H -0.1632 -0.1528 -0.0015 0.052 Uiso 1 1 calc R . . C35A C -0.15913(19) -0.00642(16) 0.02437(8) 0.0391(5) Uani 1 1 d . . . H35A H -0.1736 0.0177 -0.0113 0.047 Uiso 1 1 calc R . . C36A C -0.14384(18) 0.06126(14) 0.06981(8) 0.0316(4) Uani 1 1 d . . . C37A C -0.1003(2) -0.11919(16) 0.18568(9) 0.0489(6) Uani 1 1 d . . . H37A H -0.1279 -0.0700 0.2116 0.059 Uiso 1 1 calc R . . C38A C 0.0395(3) -0.11989(19) 0.20248(12) 0.0737(9) Uani 1 1 d . . . H38A H 0.0895 -0.0523 0.1985 0.088 Uiso 1 1 calc R . . H38B H 0.0691 -0.1696 0.1790 0.088 Uiso 1 1 calc R . . H38C H 0.0499 -0.1383 0.2408 0.088 Uiso 1 1 calc R . . C39A C -0.1796(2) -0.22229(18) 0.19273(12) 0.0649(7) Uani 1 1 d . . . H39A H -0.1627 -0.2428 0.2303 0.078 Uiso 1 1 calc R . . H39B H -0.1577 -0.2721 0.1668 0.078 Uiso 1 1 calc R . . H39C H -0.2698 -0.2187 0.1856 0.078 Uiso 1 1 calc R . . C40A C -0.1551(2) 0.17210(16) 0.06517(9) 0.0417(5) Uani 1 1 d . . . H40A H -0.0830 0.2133 0.0892 0.050 Uiso 1 1 calc R . . C41A C -0.1474(3) 0.21047(19) 0.00757(10) 0.0600(7) Uani 1 1 d . . . H41A H -0.0680 0.1988 -0.0062 0.072 Uiso 1 1 calc R . . H41B H -0.1495 0.2833 0.0085 0.072 Uiso 1 1 calc R . . H41C H -0.2196 0.1740 -0.0167 0.072 Uiso 1 1 calc R . . C42A C -0.2786(2) 0.19071(17) 0.08717(10) 0.0541(6) Uani 1 1 d . . . H42A H -0.2830 0.1659 0.1243 0.065 Uiso 1 1 calc R . . H42B H -0.3513 0.1545 0.0631 0.065 Uiso 1 1 calc R . . H42C H -0.2803 0.2636 0.0882 0.065 Uiso 1 1 calc R . . C51A C 0.08368(16) 0.43147(13) 0.36985(7) 0.0249(4) Uani 1 1 d . . . C52A C 0.11393(16) 0.39670(14) 0.42198(8) 0.0267(4) Uani 1 1 d . . . C53A C 0.13475(18) 0.46704(15) 0.46620(8) 0.0323(4) Uani 1 1 d . . . H53A H 0.1549 0.4456 0.5020 0.039 Uiso 1 1 calc R . . C54A C 0.12665(19) 0.56780(15) 0.45894(9) 0.0363(5) Uani 1 1 d . . . H54A H 0.1427 0.6151 0.4895 0.044 Uiso 1 1 calc R . . C55A C 0.09539(19) 0.59952(14) 0.40747(9) 0.0370(5) Uani 1 1 d . . . H55A H 0.0900 0.6689 0.4031 0.044 Uiso 1 1 calc R . . C56A C 0.07150(18) 0.53257(14) 0.36155(8) 0.0316(4) Uani 1 1 d . . . C57A C 0.12161(18) 0.28603(14) 0.43125(8) 0.0298(4) Uani 1 1 d . . . H57A H 0.1086 0.2485 0.3947 0.036 Uiso 1 1 calc R . . C58A C 0.0173(2) 0.23733(15) 0.46604(9) 0.0407(5) Uani 1 1 d . . . H58A H -0.0660 0.2434 0.4481 0.049 Uiso 1 1 calc R . . H58B H 0.0295 0.2720 0.5024 0.049 Uiso 1 1 calc R . . H58C H 0.0217 0.1654 0.4698 0.049 Uiso 1 1 calc R . . C59A C 0.2519(2) 0.27606(16) 0.45821(9) 0.0418(5) Uani 1 1 d . . . H59A H 0.3176 0.3066 0.4354 0.050 Uiso 1 1 calc R . . H59B H 0.2558 0.2041 0.4620 0.050 Uiso 1 1 calc R . . H59C H 0.2658 0.3111 0.4945 0.050 Uiso 1 1 calc R . . C60A C 0.0279(2) 0.56857(15) 0.30621(9) 0.0441(5) Uani 1 1 d . . . H60A H 0.0216 0.5109 0.2786 0.053 Uiso 1 1 calc R . . C61A C -0.1037(2) 0.59632(19) 0.30662(12) 0.0668(8) Uani 1 1 d . . . H61A H -0.1307 0.6174 0.2702 0.080 Uiso 1 1 calc R . . H61B H -0.1005 0.6522 0.3338 0.080 Uiso 1 1 calc R . . H61C H -0.1642 0.5372 0.3162 0.080 Uiso 1 1 calc R . . C62A C 0.1212(2) 0.65694(19) 0.28817(11) 0.0617(7) Uani 1 1 d . . . H62A H 0.2048 0.6376 0.2873 0.074 Uiso 1 1 calc R . . H62B H 0.1276 0.7153 0.3141 0.074 Uiso 1 1 calc R . . H62C H 0.0917 0.6751 0.2515 0.074 Uiso 1 1 calc R . . B1A B 0.1776(2) 0.34415(15) 0.29201(9) 0.0267(5) Uani 1 1 d . . . F1B F 0.64388(12) 0.98247(8) 0.24767(5) 0.0465(3) Uani 1 1 d . . . F2B F 0.43496(13) 0.98818(9) 0.24311(5) 0.0485(3) Uani 1 1 d . . . N11B N 0.49641(14) 0.83428(11) 0.21095(6) 0.0286(4) Uani 1 1 d . . . N12B N 0.41368(14) 0.57172(11) 0.17795(6) 0.0312(4) Uani 1 1 d . . . N21B N 0.44032(15) 0.61413(11) 0.29842(6) 0.0322(4) Uani 1 1 d . . . H21B H 0.4249 0.5559 0.2793 0.039 Uiso 1 1 calc R . . N22B N 0.51776(14) 0.88323(10) 0.31119(6) 0.0261(3) Uani 1 1 d . . . C11B C 0.46818(17) 0.73528(13) 0.22400(8) 0.0274(4) Uani 1 1 d . . . C12B C 0.44693(17) 0.66838(14) 0.17413(8) 0.0273(4) Uani 1 1 d . . . C13B C 0.47063(17) 0.73751(13) 0.12912(8) 0.0272(4) Uani 1 1 d . . . C14B C 0.49887(17) 0.83622(14) 0.15347(8) 0.0283(4) Uani 1 1 d . . . C15B C 0.52750(19) 0.92084(15) 0.12248(8) 0.0346(5) Uani 1 1 d . . . H15B H 0.5450 0.9876 0.1390 0.042 Uiso 1 1 calc R . . C16B C 0.5295(2) 0.90403(15) 0.06652(8) 0.0382(5) Uani 1 1 d . . . H16B H 0.5496 0.9605 0.0443 0.046 Uiso 1 1 calc R . . C17B C 0.50295(19) 0.80683(15) 0.04197(8) 0.0366(5) Uani 1 1 d . . . H17B H 0.5059 0.7980 0.0035 0.044 Uiso 1 1 calc R . . C18B C 0.47223(18) 0.72265(15) 0.07283(8) 0.0329(4) Uani 1 1 d . . . H18B H 0.4527 0.6563 0.0559 0.039 Uiso 1 1 calc R . . C21B C 0.46439(17) 0.70956(13) 0.27732(8) 0.0281(4) Uani 1 1 d . . . C22B C 0.48906(16) 0.78461(13) 0.32102(7) 0.0258(4) Uani 1 1 d . . . C23B C 0.47640(16) 0.73070(13) 0.37103(8) 0.0272(4) Uani 1 1 d . . . C24B C 0.44466(17) 0.62631(14) 0.35438(8) 0.0287(4) Uani 1 1 d . . . C25B C 0.42302(18) 0.55094(14) 0.39230(8) 0.0327(5) Uani 1 1 d . . . H25B H 0.4028 0.4811 0.3809 0.039 Uiso 1 1 calc R . . C26B C 0.43197(18) 0.58143(15) 0.44654(8) 0.0354(5) Uani 1 1 d . . . H26B H 0.4169 0.5315 0.4731 0.043 Uiso 1 1 calc R . . C27B C 0.46287(18) 0.68476(15) 0.46421(8) 0.0331(5) Uani 1 1 d . . . H27B H 0.4678 0.7030 0.5022 0.040 Uiso 1 1 calc R . . C28B C 0.48598(17) 0.75954(14) 0.42721(8) 0.0304(4) Uani 1 1 d . . . H28B H 0.5079 0.8290 0.4393 0.037 Uiso 1 1 calc R . . C31B C 0.39249(18) 0.50516(13) 0.13008(8) 0.0298(4) Uani 1 1 d . . . C32B C 0.49636(19) 0.47389(14) 0.10793(9) 0.0364(5) Uani 1 1 d . . . C33B C 0.4697(2) 0.40412(15) 0.06350(9) 0.0443(5) Uani 1 1 d . . . H33B H 0.5378 0.3819 0.0473 0.053 Uiso 1 1 calc R . . C34B C 0.3470(2) 0.36634(17) 0.04235(10) 0.0487(6) Uani 1 1 d . . . H34B H 0.3315 0.3189 0.0118 0.058 Uiso 1 1 calc R . . C35B C 0.2462(2) 0.39701(16) 0.06522(9) 0.0433(5) Uani 1 1 d . . . H35B H 0.1619 0.3701 0.0503 0.052 Uiso 1 1 calc R . . C36B C 0.26621(19) 0.46669(14) 0.10979(8) 0.0330(5) Uani 1 1 d . . . C37B C 0.6310(2) 0.51203(17) 0.13343(10) 0.0476(6) Uani 1 1 d . . . H37B H 0.6345 0.5829 0.1484 0.057 Uiso 1 1 calc R . . C38B C 0.7302(2) 0.5167(2) 0.09292(12) 0.0639(7) Uani 1 1 d . . . H38D H 0.8143 0.5427 0.1119 0.077 Uiso 1 1 calc R . . H38E H 0.7120 0.5619 0.0638 0.077 Uiso 1 1 calc R . . H38F H 0.7285 0.4485 0.0769 0.077 Uiso 1 1 calc R . . C39B C 0.6626(2) 0.4488(2) 0.18176(11) 0.0713(8) Uani 1 1 d . . . H39D H 0.7496 0.4747 0.1978 0.086 Uiso 1 1 calc R . . H39E H 0.6552 0.3778 0.1690 0.086 Uiso 1 1 calc R . . H39F H 0.6034 0.4535 0.2095 0.086 Uiso 1 1 calc R . . C40B C 0.15810(19) 0.50293(15) 0.13590(9) 0.0394(5) Uani 1 1 d . . . H40B H 0.1885 0.5233 0.1751 0.047 Uiso 1 1 calc R . . C41B C 0.1246(2) 0.59679(17) 0.10849(12) 0.0612(7) Uani 1 1 d . . . H41D H 0.2009 0.6495 0.1096 0.073 Uiso 1 1 calc R . . H41E H 0.0602 0.6224 0.1281 0.073 Uiso 1 1 calc R . . H41F H 0.0913 0.5787 0.0703 0.073 Uiso 1 1 calc R . . C42B C 0.0402(2) 0.42151(17) 0.13566(10) 0.0511(6) Uani 1 1 d . . . H42D H 0.0627 0.3614 0.1530 0.061 Uiso 1 1 calc R . . H42E H 0.0045 0.4031 0.0978 0.061 Uiso 1 1 calc R . . H42F H -0.0228 0.4474 0.1561 0.061 Uiso 1 1 calc R . . C51B C 0.54862(17) 0.95500(13) 0.35835(7) 0.0256(4) Uani 1 1 d . . . C52B C 0.67445(17) 0.97701(14) 0.38162(8) 0.0293(4) Uani 1 1 d . . . C53B C 0.70107(19) 1.04431(15) 0.42739(8) 0.0363(5) Uani 1 1 d . . . H53B H 0.7858 1.0616 0.4440 0.044 Uiso 1 1 calc R . . C54B C 0.6069(2) 1.08635(16) 0.44911(9) 0.0410(5) Uani 1 1 d . . . H54B H 0.6272 1.1318 0.4804 0.049 Uiso 1 1 calc R . . C55B C 0.4836(2) 1.06257(15) 0.42553(8) 0.0376(5) Uani 1 1 d . . . H55B H 0.4196 1.0919 0.4409 0.045 Uiso 1 1 calc R . . C56B C 0.45107(18) 0.99618(14) 0.37948(8) 0.0296(4) Uani 1 1 d . . . C57B C 0.77944(18) 0.92836(15) 0.36045(9) 0.0351(5) Uani 1 1 d . . . H57B H 0.7429 0.8860 0.3266 0.042 Uiso 1 1 calc R . . C58B C 0.8273(2) 0.85822(18) 0.40233(11) 0.0550(7) Uani 1 1 d . . . H58D H 0.7556 0.8082 0.4121 0.066 Uiso 1 1 calc R . . H58E H 0.8678 0.8985 0.4353 0.066 Uiso 1 1 calc R . . H58F H 0.8890 0.8231 0.3864 0.066 Uiso 1 1 calc R . . C59B C 0.8894(2) 1.00703(17) 0.34513(10) 0.0485(6) Uani 1 1 d . . . H59D H 0.8577 1.0514 0.3182 0.058 Uiso 1 1 calc R . . H59E H 0.9519 0.9727 0.3293 0.058 Uiso 1 1 calc R . . H59F H 0.9293 1.0478 0.3780 0.058 Uiso 1 1 calc R . . C60B C 0.31320(18) 0.96915(15) 0.35528(9) 0.0356(5) Uani 1 1 d . . . H60B H 0.3089 0.9194 0.3236 0.043 Uiso 1 1 calc R . . C61B C 0.2283(2) 0.91827(18) 0.39731(10) 0.0522(6) Uani 1 1 d . . . H61D H 0.2600 0.8581 0.4102 0.063 Uiso 1 1 calc R . . H61E H 0.1412 0.8980 0.3802 0.063 Uiso 1 1 calc R . . H61F H 0.2293 0.9661 0.4285 0.063 Uiso 1 1 calc R . . C62B C 0.2644(2) 1.06268(16) 0.33373(10) 0.0458(6) Uani 1 1 d . . . H62D H 0.3191 1.0936 0.3065 0.055 Uiso 1 1 calc R . . H62E H 0.2657 1.1120 0.3643 0.055 Uiso 1 1 calc R . . H62F H 0.1773 1.0422 0.3166 0.055 Uiso 1 1 calc R . . B1B B 0.5232(2) 0.92559(16) 0.25230(9) 0.0312(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1A 0.0271(6) 0.0459(7) 0.0344(6) -0.0052(5) -0.0038(5) 0.0102(5) F2A 0.0456(7) 0.0256(6) 0.0440(7) -0.0014(5) 0.0126(5) -0.0041(5) N11A 0.0301(8) 0.0206(7) 0.0252(8) -0.0002(6) 0.0032(7) 0.0049(6) N12A 0.0326(9) 0.0224(8) 0.0262(9) 0.0006(7) -0.0019(7) 0.0053(7) N21A 0.0276(8) 0.0249(8) 0.0290(9) -0.0041(7) -0.0025(7) 0.0015(6) N22A 0.0277(8) 0.0197(7) 0.0242(8) -0.0006(6) -0.0007(6) 0.0052(6) C11A 0.0274(10) 0.0194(9) 0.0241(10) 0.0005(7) -0.0006(8) 0.0034(7) C12A 0.0332(10) 0.0194(9) 0.0236(10) 0.0035(7) 0.0014(8) 0.0079(8) C13A 0.0307(10) 0.0223(9) 0.0275(10) 0.0017(8) 0.0019(8) 0.0064(8) C14A 0.0328(10) 0.0236(9) 0.0261(10) 0.0040(8) 0.0038(8) 0.0075(8) C15A 0.0323(11) 0.0329(11) 0.0331(12) -0.0027(9) 0.0006(9) 0.0052(9) C16A 0.0294(11) 0.0456(13) 0.0446(13) -0.0011(10) 0.0068(10) 0.0067(9) C17A 0.0387(12) 0.0436(12) 0.0381(12) -0.0052(10) 0.0101(10) 0.0113(10) C18A 0.0392(11) 0.0305(10) 0.0292(11) -0.0041(8) 0.0028(9) 0.0078(9) C21A 0.0299(10) 0.0178(9) 0.0255(10) 0.0017(7) 0.0006(8) 0.0043(7) C22A 0.0251(9) 0.0187(9) 0.0270(10) 0.0023(7) -0.0009(8) 0.0047(7) C23A 0.0258(9) 0.0243(9) 0.0270(10) 0.0033(8) 0.0007(8) 0.0088(7) C24A 0.0306(10) 0.0226(9) 0.0293(11) 0.0030(8) 0.0004(8) 0.0061(8) C25A 0.0248(10) 0.0333(11) 0.0425(13) 0.0025(9) -0.0023(9) 0.0027(8) C26A 0.0287(11) 0.0423(12) 0.0494(14) 0.0021(10) 0.0055(10) 0.0102(9) C27A 0.0332(11) 0.0405(12) 0.0407(13) -0.0039(10) 0.0078(9) 0.0136(9) C28A 0.0295(10) 0.0308(10) 0.0327(11) -0.0002(8) 0.0000(8) 0.0095(8) C31A 0.0282(10) 0.0271(10) 0.0280(11) -0.0029(8) 0.0014(8) 0.0049(8) C32A 0.0384(11) 0.0269(10) 0.0374(12) 0.0003(9) 0.0010(9) 0.0081(8) C33A 0.0514(14) 0.0289(11) 0.0486(14) -0.0079(10) 0.0022(11) 0.0114(10) C34A 0.0467(13) 0.0432(13) 0.0373(13) -0.0152(10) 0.0011(10) 0.0045(10) C35A 0.0409(12) 0.0454(13) 0.0288(11) -0.0017(10) -0.0014(9) 0.0044(10) C36A 0.0302(10) 0.0331(11) 0.0299(11) 0.0014(9) 0.0005(8) 0.0024(8) C37A 0.0742(17) 0.0310(12) 0.0433(14) 0.0036(10) -0.0046(12) 0.0193(11) C38A 0.0768(19) 0.0488(15) 0.083(2) 0.0256(14) -0.0358(16) -0.0055(13) C39A 0.0632(17) 0.0556(16) 0.079(2) 0.0282(14) 0.0067(14) 0.0155(13) C40A 0.0529(14) 0.0343(12) 0.0362(13) 0.0085(10) -0.0049(10) 0.0068(10) C41A 0.0725(18) 0.0556(15) 0.0528(16) 0.0210(13) 0.0022(13) 0.0127(13) C42A 0.0748(18) 0.0400(13) 0.0538(15) 0.0045(11) 0.0005(13) 0.0297(12) C51A 0.0227(9) 0.0242(9) 0.0272(10) -0.0041(8) 0.0008(8) 0.0047(7) C52A 0.0215(9) 0.0306(10) 0.0274(10) -0.0008(8) 0.0008(8) 0.0037(8) C53A 0.0302(10) 0.0380(11) 0.0278(11) -0.0035(9) 0.0026(8) 0.0049(9) C54A 0.0355(11) 0.0332(11) 0.0386(13) -0.0112(9) 0.0043(9) 0.0038(9) C55A 0.0419(12) 0.0237(10) 0.0457(13) -0.0025(9) 0.0058(10) 0.0069(9) C56A 0.0319(10) 0.0267(10) 0.0366(12) 0.0001(9) 0.0014(9) 0.0078(8) C57A 0.0372(11) 0.0278(10) 0.0258(10) 0.0019(8) 0.0006(8) 0.0106(8) C58A 0.0442(12) 0.0337(11) 0.0439(13) 0.0082(10) 0.0021(10) 0.0067(9) C59A 0.0427(12) 0.0452(12) 0.0410(13) 0.0060(10) 0.0019(10) 0.0175(10) C60A 0.0648(15) 0.0274(11) 0.0415(13) 0.0016(9) -0.0032(11) 0.0159(10) C61A 0.0564(16) 0.0537(15) 0.087(2) 0.0252(14) -0.0200(14) 0.0112(12) C62A 0.0647(17) 0.0581(16) 0.0674(18) 0.0259(13) 0.0106(14) 0.0186(13) B1A 0.0269(11) 0.0227(11) 0.0286(12) -0.0012(9) 0.0009(9) 0.0002(8) F1B 0.0573(8) 0.0364(7) 0.0366(7) -0.0011(5) 0.0067(6) -0.0171(6) F2B 0.0754(9) 0.0379(7) 0.0382(7) 0.0027(5) 0.0010(6) 0.0285(6) N11B 0.0348(9) 0.0242(8) 0.0262(9) -0.0009(7) 0.0021(7) 0.0041(7) N12B 0.0305(9) 0.0265(9) 0.0353(10) -0.0028(7) 0.0025(7) 0.0027(7) N21B 0.0435(10) 0.0202(8) 0.0313(9) -0.0022(7) 0.0022(7) 0.0032(7) N22B 0.0278(8) 0.0208(8) 0.0289(9) -0.0022(6) 0.0019(7) 0.0035(6) C11B 0.0278(10) 0.0226(9) 0.0306(11) -0.0019(8) 0.0004(8) 0.0030(7) C12B 0.0249(10) 0.0268(10) 0.0303(11) -0.0004(8) 0.0022(8) 0.0054(8) C13B 0.0268(10) 0.0256(10) 0.0286(11) -0.0013(8) 0.0008(8) 0.0042(8) C14B 0.0266(10) 0.0307(10) 0.0271(11) -0.0013(8) 0.0006(8) 0.0049(8) C15B 0.0413(12) 0.0281(11) 0.0328(12) -0.0001(9) -0.0007(9) 0.0040(9) C16B 0.0438(12) 0.0338(11) 0.0354(12) 0.0070(9) -0.0004(10) 0.0044(9) C17B 0.0399(12) 0.0443(12) 0.0249(11) 0.0010(9) -0.0001(9) 0.0074(10) C18B 0.0360(11) 0.0322(11) 0.0291(11) -0.0025(9) -0.0003(9) 0.0049(8) C21B 0.0304(10) 0.0229(9) 0.0294(11) -0.0021(8) 0.0014(8) 0.0019(8) C22B 0.0234(9) 0.0247(10) 0.0281(10) 0.0004(8) 0.0017(8) 0.0018(7) C23B 0.0237(9) 0.0282(10) 0.0293(11) 0.0010(8) 0.0026(8) 0.0034(8) C24B 0.0270(10) 0.0279(10) 0.0301(11) 0.0004(8) -0.0007(8) 0.0036(8) C25B 0.0311(11) 0.0262(10) 0.0390(12) 0.0051(9) -0.0013(9) 0.0022(8) C26B 0.0311(11) 0.0378(12) 0.0360(12) 0.0118(9) -0.0016(9) 0.0030(9) C27B 0.0296(10) 0.0417(12) 0.0259(11) 0.0021(9) -0.0005(8) 0.0028(9) C28B 0.0278(10) 0.0295(10) 0.0322(11) 0.0005(8) 0.0006(8) 0.0016(8) C31B 0.0402(11) 0.0190(9) 0.0290(11) -0.0009(8) 0.0034(9) 0.0030(8) C32B 0.0393(12) 0.0250(10) 0.0440(13) -0.0027(9) 0.0064(10) 0.0033(9) C33B 0.0527(14) 0.0338(12) 0.0474(14) -0.0098(10) 0.0102(11) 0.0097(10) C34B 0.0589(15) 0.0411(13) 0.0429(14) -0.0122(11) -0.0004(12) 0.0057(11) C35B 0.0467(13) 0.0374(12) 0.0416(13) -0.0067(10) -0.0090(10) 0.0038(10) C36B 0.0369(11) 0.0260(10) 0.0341(12) 0.0032(9) -0.0012(9) 0.0022(8) C37B 0.0384(12) 0.0345(12) 0.0687(17) -0.0168(11) 0.0074(12) 0.0051(10) C38B 0.0461(15) 0.0624(16) 0.087(2) 0.0128(15) 0.0158(14) 0.0143(12) C39B 0.0496(16) 0.100(2) 0.0559(17) -0.0026(16) -0.0095(13) -0.0017(15) C40B 0.0362(12) 0.0378(12) 0.0434(13) 0.0014(10) -0.0011(10) 0.0069(9) C41B 0.0433(14) 0.0389(13) 0.104(2) 0.0133(13) 0.0105(14) 0.0092(11) C42B 0.0409(13) 0.0438(13) 0.0684(17) 0.0144(12) 0.0005(12) 0.0074(10) C51B 0.0297(10) 0.0182(9) 0.0276(10) 0.0000(8) 0.0026(8) 0.0013(7) C52B 0.0282(10) 0.0265(10) 0.0326(11) 0.0013(8) 0.0033(8) 0.0032(8) C53B 0.0322(11) 0.0355(11) 0.0368(12) -0.0032(9) -0.0065(9) 0.0001(9) C54B 0.0491(14) 0.0365(12) 0.0358(12) -0.0099(10) 0.0025(10) 0.0062(10) C55B 0.0401(12) 0.0339(11) 0.0408(13) -0.0064(9) 0.0107(10) 0.0106(9) C56B 0.0312(10) 0.0241(10) 0.0337(11) 0.0003(8) 0.0049(8) 0.0049(8) C57B 0.0283(10) 0.0380(11) 0.0390(12) 0.0005(9) 0.0017(9) 0.0070(9) C58B 0.0448(14) 0.0507(14) 0.0765(18) 0.0217(13) 0.0145(12) 0.0197(11) C59B 0.0368(12) 0.0537(14) 0.0581(15) 0.0160(12) 0.0105(11) 0.0112(10) C60B 0.0272(10) 0.0321(11) 0.0474(13) -0.0034(9) 0.0037(9) 0.0058(8) C61B 0.0318(12) 0.0534(14) 0.0716(17) 0.0135(12) 0.0090(11) 0.0047(10) C62B 0.0340(12) 0.0438(13) 0.0614(15) 0.0055(11) 0.0029(11) 0.0120(10) B1B 0.0406(13) 0.0215(11) 0.0294(12) -0.0015(9) 0.0018(10) 0.0008(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1A B1A 1.392(2) . ? F2A B1A 1.402(2) . ? N11A C11A 1.357(2) . ? N11A C14A 1.418(2) . ? N11A B1A 1.537(3) . ? N12A C12A 1.280(2) . ? N12A C31A 1.425(2) . ? N21A C24A 1.375(2) . ? N21A C21A 1.382(2) . ? N22A C22A 1.336(2) . ? N22A C51A 1.452(2) . ? N22A B1A 1.559(3) . ? C11A C21A 1.370(3) . ? C11A C12A 1.476(2) . ? C12A C13A 1.474(3) . ? C13A C18A 1.391(3) . ? C13A C14A 1.408(3) . ? C14A C15A 1.382(3) . ? C15A C16A 1.392(3) . ? C16A C17A 1.392(3) . ? C17A C18A 1.383(3) . ? C21A C22A 1.423(2) . ? C22A C23A 1.444(2) . ? C23A C28A 1.405(3) . ? C23A C24A 1.423(2) . ? C24A C25A 1.389(3) . ? C25A C26A 1.373(3) . ? C26A C27A 1.397(3) . ? C27A C28A 1.381(3) . ? C31A C36A 1.403(3) . ? C31A C32A 1.407(3) . ? C32A C33A 1.390(3) . ? C32A C37A 1.516(3) . ? C33A C34A 1.376(3) . ? C34A C35A 1.385(3) . ? C35A C36A 1.393(3) . ? C36A C40A 1.518(3) . ? C37A C39A 1.512(3) . ? C37A C38A 1.526(3) . ? C40A C41A 1.521(3) . ? C40A C42A 1.533(3) . ? C51A C56A 1.403(2) . ? C51A C52A 1.405(3) . ? C52A C53A 1.390(3) . ? C52A C57A 1.523(2) . ? C53A C54A 1.384(3) . ? C54A C55A 1.376(3) . ? C55A C56A 1.393(3) . ? C56A C60A 1.517(3) . ? C57A C59A 1.525(3) . ? C57A C58A 1.534(3) . ? C60A C62A 1.514(3) . ? C60A C61A 1.526(3) . ? F1B B1B 1.399(2) . ? F2B B1B 1.382(3) . ? N11B C11B 1.362(2) . ? N11B C14B 1.412(2) . ? N11B B1B 1.534(3) . ? N12B C12B 1.289(2) . ? N12B C31B 1.428(2) . ? N21B C24B 1.371(2) . ? N21B C21B 1.384(2) . ? N22B C22B 1.337(2) . ? N22B C51B 1.456(2) . ? N22B B1B 1.569(3) . ? C11B C21B 1.364(3) . ? C11B C12B 1.469(3) . ? C12B C13B 1.473(2) . ? C13B C18B 1.389(3) . ? C13B C14B 1.405(3) . ? C14B C15B 1.388(3) . ? C15B C16B 1.385(3) . ? C16B C17B 1.389(3) . ? C17B C18B 1.385(3) . ? C21B C22B 1.420(2) . ? C22B C23B 1.446(2) . ? C23B C28B 1.408(3) . ? C23B C24B 1.418(3) . ? C24B C25B 1.396(3) . ? C25B C26B 1.368(3) . ? C26B C27B 1.410(3) . ? C27B C28B 1.377(3) . ? C31B C36B 1.405(3) . ? C31B C32B 1.406(3) . ? C32B C33B 1.388(3) . ? C32B C37B 1.519(3) . ? C33B C34B 1.375(3) . ? C34B C35B 1.382(3) . ? C35B C36B 1.391(3) . ? C36B C40B 1.519(3) . ? C37B C38B 1.514(3) . ? C37B C39B 1.526(3) . ? C40B C42B 1.518(3) . ? C40B C41B 1.528(3) . ? C51B C52B 1.398(2) . ? C51B C56B 1.399(3) . ? C52B C53B 1.393(3) . ? C52B C57B 1.521(3) . ? C53B C54B 1.380(3) . ? C54B C55B 1.378(3) . ? C55B C56B 1.394(3) . ? C56B C60B 1.524(3) . ? C57B C59B 1.519(3) . ? C57B C58B 1.530(3) . ? C60B C61B 1.532(3) . ? C60B C62B 1.533(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 C11A N11A C14A 108.01(14) . . ? C11A N11A B1A 124.95(15) . . ? C14A N11A B1A 126.98(15) . . ? C12A N12A C31A 119.74(16) . . ? C24A N21A C21A 108.35(15) . . ? C22A N22A C51A 118.44(14) . . ? C22A N22A B1A 123.85(15) . . ? C51A N22A B1A 117.70(14) . . ? N11A C11A C21A 120.87(16) . . ? N11A C11A C12A 110.54(15) . . ? C21A C11A C12A 128.58(16) . . ? N12A C12A C13A 135.58(17) . . ? N12A C12A C11A 120.18(16) . . ? C13A C12A C11A 104.24(15) . . ? C18A C13A C14A 119.72(17) . . ? C18A C13A C12A 133.49(17) . . ? C14A C13A C12A 106.78(16) . . ? C15A C14A C13A 121.93(17) . . ? C15A C14A N11A 127.66(17) . . ? C13A C14A N11A 110.41(16) . . ? C14A C15A C16A 117.11(19) . . ? C17A C16A C15A 121.88(19) . . ? C18A C17A C16A 120.47(19) . . ? C17A C18A C13A 118.89(18) . . ? C11A C21A N21A 129.53(16) . . ? C11A C21A C22A 121.08(16) . . ? N21A C21A C22A 109.39(15) . . ? N22A C22A C21A 121.20(16) . . ? N22A C22A C23A 132.37(16) . . ? C21A C22A C23A 106.43(15) . . ? C28A C23A C24A 119.10(16) . . ? C28A C23A C22A 135.04(17) . . ? C24A C23A C22A 105.85(16) . . ? N21A C24A C25A 128.37(17) . . ? N21A C24A C23A 109.96(16) . . ? C25A C24A C23A 121.65(18) . . ? C26A C25A C24A 117.63(18) . . ? C25A C26A C27A 122.03(19) . . ? C28A C27A C26A 120.96(19) . . ? C27A C28A C23A 118.62(18) . . ? C36A C31A C32A 122.23(17) . . ? C36A C31A N12A 119.11(16) . . ? C32A C31A N12A 118.44(16) . . ? C33A C32A C31A 117.39(18) . . ? C33A C32A C37A 122.68(18) . . ? C31A C32A C37A 119.92(18) . . ? C34A C33A C32A 121.64(19) . . ? C33A C34A C35A 119.9(2) . . ? C34A C35A C36A 121.37(19) . . ? C35A C36A C31A 117.39(18) . . ? C35A C36A C40A 122.66(18) . . ? C31A C36A C40A 119.92(17) . . ? C39A C37A C32A 113.54(19) . . ? C39A C37A C38A 110.40(19) . . ? C32A C37A C38A 111.2(2) . . ? C36A C40A C41A 114.46(19) . . ? C36A C40A C42A 109.96(17) . . ? C41A C40A C42A 109.81(19) . . ? C56A C51A C52A 122.51(17) . . ? C56A C51A N22A 118.77(16) . . ? C52A C51A N22A 118.70(15) . . ? C53A C52A C51A 117.58(17) . . ? C53A C52A C57A 119.96(17) . . ? C51A C52A C57A 122.44(16) . . ? C54A C53A C52A 121.06(19) . . ? C55A C54A C53A 120.10(19) . . ? C54A C55A C56A 121.71(18) . . ? C55A C56A C51A 116.99(18) . . ? C55A C56A C60A 120.19(17) . . ? C51A C56A C60A 122.74(17) . . ? C52A C57A C59A 111.06(16) . . ? C52A C57A C58A 111.14(15) . . ? C59A C57A C58A 110.19(16) . . ? C62A C60A C56A 112.26(19) . . ? C62A C60A C61A 110.33(19) . . ? C56A C60A C61A 111.01(19) . . ? F1A B1A F2A 107.29(15) . . ? F1A B1A N11A 111.03(15) . . ? F2A B1A N11A 110.15(15) . . ? F1A B1A N22A 110.38(15) . . ? F2A B1A N22A 109.96(15) . . ? N11A B1A N22A 108.04(14) . . ? C11B N11B C14B 107.61(15) . . ? C11B N11B B1B 125.20(16) . . ? C14B N11B B1B 127.17(15) . . ? C12B N12B C31B 120.64(16) . . ? C24B N21B C21B 108.02(15) . . ? C22B N22B C51B 117.52(15) . . ? C22B N22B B1B 124.06(15) . . ? C51B N22B B1B 118.41(14) . . ? N11B C11B C21B 120.85(17) . . ? N11B C11B C12B 110.42(16) . . ? C21B C11B C12B 128.73(16) . . ? N12B C12B C11B 119.60(17) . . ? N12B C12B C13B 135.75(18) . . ? C11B C12B C13B 104.64(15) . . ? C18B C13B C14B 120.07(17) . . ? C18B C13B C12B 133.67(17) . . ? C14B C13B C12B 106.24(16) . . ? C15B C14B C13B 121.55(18) . . ? C15B C14B N11B 127.40(17) . . ? C13B C14B N11B 111.04(16) . . ? C16B C15B C14B 117.30(18) . . ? C15B C16B C17B 121.76(19) . . ? C18B C17B C16B 120.84(19) . . ? C17B C18B C13B 118.47(18) . . ? C11B C21B N21B 129.10(17) . . ? C11B C21B C22B 121.41(16) . . ? N21B C21B C22B 109.48(16) . . ? N22B C22B C21B 120.92(16) . . ? N22B C22B C23B 132.74(17) . . ? C21B C22B C23B 106.35(15) . . ? C28B C23B C24B 119.36(17) . . ? C28B C23B C22B 134.92(17) . . ? C24B C23B C22B 105.71(16) . . ? N21B C24B C25B 127.89(17) . . ? N21B C24B C23B 110.40(16) . . ? C25B C24B C23B 121.71(18) . . ? C26B C25B C24B 117.54(18) . . ? C25B C26B C27B 121.90(18) . . ? C28B C27B C26B 121.00(18) . . ? C27B C28B C23B 118.48(17) . . ? C36B C31B C32B 122.49(18) . . ? C36B C31B N12B 117.75(17) . . ? C32B C31B N12B 119.54(17) . . ? C33B C32B C31B 117.11(19) . . ? C33B C32B C37B 121.99(19) . . ? C31B C32B C37B 120.85(18) . . ? C34B C33B C32B 121.6(2) . . ? C33B C34B C35B 120.4(2) . . ? C34B C35B C36B 121.0(2) . . ? C35B C36B C31B 117.44(19) . . ? C35B C36B C40B 122.64(18) . . ? C31B C36B C40B 119.91(17) . . ? C38B C37B C32B 113.7(2) . . ? C38B C37B C39B 110.8(2) . . ? C32B C37B C39B 110.61(19) . . ? C42B C40B C36B 113.42(18) . . ? C42B C40B C41B 110.04(18) . . ? C36B C40B C41B 110.92(18) . . ? C52B C51B C56B 122.91(17) . . ? C52B C51B N22B 118.18(16) . . ? C56B C51B N22B 118.88(16) . . ? C53B C52B C51B 117.09(17) . . ? C53B C52B C57B 119.86(17) . . ? C51B C52B C57B 123.02(17) . . ? C54B C53B C52B 121.34(19) . . ? C55B C54B C53B 120.23(19) . . ? C54B C55B C56B 121.14(19) . . ? C55B C56B C51B 117.29(17) . . ? C55B C56B C60B 119.88(17) . . ? C51B C56B C60B 122.81(17) . . ? C59B C57B C52B 112.06(17) . . ? C59B C57B C58B 110.15(17) . . ? C52B C57B C58B 111.09(17) . . ? C56B C60B C61B 111.00(17) . . ? C56B C60B C62B 111.47(16) . . ? C61B C60B C62B 110.58(17) . . ? F2B B1B F1B 108.30(16) . . ? F2B B1B N11B 111.02(17) . . ? F1B B1B N11B 110.09(16) . . ? F2B B1B N22B 110.41(16) . . ? F1B B1B N22B 109.51(16) . . ? N11B B1B N22B 107.51(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14A N11A C11A C21A -178.58(16) . . . . ? B1A N11A C11A C21A -1.1(3) . . . . ? C14A N11A C11A C12A 0.33(19) . . . . ? B1A N11A C11A C12A 177.79(15) . . . . ? C31A N12A C12A C13A -3.0(3) . . . . ? C31A N12A C12A C11A 177.51(15) . . . . ? N11A C11A C12A N12A 178.82(15) . . . . ? C21A C11A C12A N12A -2.4(3) . . . . ? N11A C11A C12A C13A -0.78(18) . . . . ? C21A C11A C12A C13A 178.02(17) . . . . ? N12A C12A C13A C18A 0.3(4) . . . . ? C11A C12A C13A C18A 179.77(19) . . . . ? N12A C12A C13A C14A -178.6(2) . . . . ? C11A C12A C13A C14A 0.91(18) . . . . ? C18A C13A C14A C15A 0.3(3) . . . . ? C12A C13A C14A C15A 179.30(17) . . . . ? C18A C13A C14A N11A -179.81(16) . . . . ? C12A C13A C14A N11A -0.77(19) . . . . ? C11A N11A C14A C15A -179.78(18) . . . . ? B1A N11A C14A C15A 2.8(3) . . . . ? C11A N11A C14A C13A 0.29(19) . . . . ? B1A N11A C14A C13A -177.11(16) . . . . ? C13A C14A C15A C16A -0.7(3) . . . . ? N11A C14A C15A C16A 179.42(18) . . . . ? C14A C15A C16A C17A 0.4(3) . . . . ? C15A C16A C17A C18A 0.3(3) . . . . ? C16A C17A C18A C13A -0.7(3) . . . . ? C14A C13A C18A C17A 0.4(3) . . . . ? C12A C13A C18A C17A -178.30(19) . . . . ? N11A C11A C21A N21A 178.89(16) . . . . ? C12A C11A C21A N21A 0.2(3) . . . . ? N11A C11A C21A C22A -0.3(3) . . . . ? C12A C11A C21A C22A -178.96(16) . . . . ? C24A N21A C21A C11A 179.01(18) . . . . ? C24A N21A C21A C22A -1.75(19) . . . . ? C51A N22A C22A C21A -178.83(15) . . . . ? B1A N22A C22A C21A -0.4(2) . . . . ? C51A N22A C22A C23A 1.9(3) . . . . ? B1A N22A C22A C23A -179.69(17) . . . . ? C11A C21A C22A N22A 1.0(3) . . . . ? N21A C21A C22A N22A -178.27(15) . . . . ? C11A C21A C22A C23A -179.53(16) . . . . ? N21A C21A C22A C23A 1.16(19) . . . . ? N22A C22A C23A C28A 0.5(3) . . . . ? C21A C22A C23A C28A -178.87(19) . . . . ? N22A C22A C23A C24A 179.19(18) . . . . ? C21A C22A C23A C24A -0.14(19) . . . . ? C21A N21A C24A C25A 179.86(18) . . . . ? C21A N21A C24A C23A 1.67(19) . . . . ? C28A C23A C24A N21A 178.04(16) . . . . ? C22A C23A C24A N21A -0.93(19) . . . . ? C28A C23A C24A C25A -0.3(3) . . . . ? C22A C23A C24A C25A -179.26(17) . . . . ? N21A C24A C25A C26A -177.24(18) . . . . ? C23A C24A C25A C26A 0.8(3) . . . . ? C24A C25A C26A C27A -0.6(3) . . . . ? C25A C26A C27A C28A -0.1(3) . . . . ? C26A C27A C28A C23A 0.6(3) . . . . ? C24A C23A C28A C27A -0.4(3) . . . . ? C22A C23A C28A C27A 178.18(19) . . . . ? C12A N12A C31A C36A -86.8(2) . . . . ? C12A N12A C31A C32A 98.5(2) . . . . ? C36A C31A C32A C33A 3.1(3) . . . . ? N12A C31A C32A C33A 177.64(17) . . . . ? C36A C31A C32A C37A -176.93(19) . . . . ? N12A C31A C32A C37A -2.4(3) . . . . ? C31A C32A C33A C34A -1.2(3) . . . . ? C37A C32A C33A C34A 178.8(2) . . . . ? C32A C33A C34A C35A -0.7(3) . . . . ? C33A C34A C35A C36A 0.9(3) . . . . ? C34A C35A C36A C31A 0.9(3) . . . . ? C34A C35A C36A C40A -177.20(19) . . . . ? C32A C31A C36A C35A -2.9(3) . . . . ? N12A C31A C36A C35A -177.42(16) . . . . ? C32A C31A C36A C40A 175.21(18) . . . . ? N12A C31A C36A C40A 0.7(3) . . . . ? C33A C32A C37A C39A -38.4(3) . . . . ? C31A C32A C37A C39A 141.7(2) . . . . ? C33A C32A C37A C38A 86.9(3) . . . . ? C31A C32A C37A C38A -93.1(2) . . . . ? C35A C36A C40A C41A -16.3(3) . . . . ? C31A C36A C40A C41A 165.72(19) . . . . ? C35A C36A C40A C42A 107.9(2) . . . . ? C31A C36A C40A C42A -70.1(2) . . . . ? C22A N22A C51A C56A -89.5(2) . . . . ? B1A N22A C51A C56A 92.05(19) . . . . ? C22A N22A C51A C52A 89.1(2) . . . . ? B1A N22A C51A C52A -89.40(19) . . . . ? C56A C51A C52A C53A -1.4(3) . . . . ? N22A C51A C52A C53A -179.87(15) . . . . ? C56A C51A C52A C57A 177.34(17) . . . . ? N22A C51A C52A C57A -1.2(2) . . . . ? C51A C52A C53A C54A -0.4(3) . . . . ? C57A C52A C53A C54A -179.13(17) . . . . ? C52A C53A C54A C55A 1.1(3) . . . . ? C53A C54A C55A C56A -0.2(3) . . . . ? C54A C55A C56A C51A -1.5(3) . . . . ? C54A C55A C56A C60A 175.49(19) . . . . ? C52A C51A C56A C55A 2.3(3) . . . . ? N22A C51A C56A C55A -179.23(16) . . . . ? C52A C51A C56A C60A -174.61(18) . . . . ? N22A C51A C56A C60A 3.9(3) . . . . ? C53A C52A C57A C59A -58.6(2) . . . . ? C51A C52A C57A C59A 122.73(19) . . . . ? C53A C52A C57A C58A 64.5(2) . . . . ? C51A C52A C57A C58A -114.22(19) . . . . ? C55A C56A C60A C62A 58.1(3) . . . . ? C51A C56A C60A C62A -125.1(2) . . . . ? C55A C56A C60A C61A -65.9(3) . . . . ? C51A C56A C60A C61A 110.9(2) . . . . ? C11A N11A B1A F1A 122.70(18) . . . . ? C14A N11A B1A F1A -60.3(2) . . . . ? C11A N11A B1A F2A -118.60(18) . . . . ? C14A N11A B1A F2A 58.4(2) . . . . ? C11A N11A B1A N22A 1.5(2) . . . . ? C14A N11A B1A N22A 178.50(15) . . . . ? C22A N22A B1A F1A -122.31(17) . . . . ? C51A N22A B1A F1A 56.09(19) . . . . ? C22A N22A B1A F2A 119.51(17) . . . . ? C51A N22A B1A F2A -62.1(2) . . . . ? C22A N22A B1A N11A -0.7(2) . . . . ? C51A N22A B1A N11A 177.67(14) . . . . ? C14B N11B C11B C21B 177.28(17) . . . . ? B1B N11B C11B C21B -1.5(3) . . . . ? C14B N11B C11B C12B -1.8(2) . . . . ? B1B N11B C11B C12B 179.38(17) . . . . ? C31B N12B C12B C11B 180.00(16) . . . . ? C31B N12B C12B C13B 0.9(3) . . . . ? N11B C11B C12B N12B -177.07(16) . . . . ? C21B C11B C12B N12B 3.9(3) . . . . ? N11B C11B C12B C13B 2.3(2) . . . . ? C21B C11B C12B C13B -176.73(18) . . . . ? N12B C12B C13B C18B -4.2(4) . . . . ? C11B C12B C13B C18B 176.6(2) . . . . ? N12B C12B C13B C14B 177.4(2) . . . . ? C11B C12B C13B C14B -1.81(19) . . . . ? C18B C13B C14B C15B 0.7(3) . . . . ? C12B C13B C14B C15B 179.40(17) . . . . ? C18B C13B C14B N11B -177.90(16) . . . . ? C12B C13B C14B N11B 0.8(2) . . . . ? C11B N11B C14B C15B -177.87(19) . . . . ? B1B N11B C14B C15B 0.9(3) . . . . ? C11B N11B C14B C13B 0.6(2) . . . . ? B1B N11B C14B C13B 179.38(17) . . . . ? C13B C14B C15B C16B -1.2(3) . . . . ? N11B C14B C15B C16B 177.15(18) . . . . ? C14B C15B C16B C17B 0.6(3) . . . . ? C15B C16B C17B C18B 0.5(3) . . . . ? C16B C17B C18B C13B -1.0(3) . . . . ? C14B C13B C18B C17B 0.4(3) . . . . ? C12B C13B C18B C17B -177.84(19) . . . . ? N11B C11B C21B N21B -178.55(17) . . . . ? C12B C11B C21B N21B 0.4(3) . . . . ? N11B C11B C21B C22B 0.3(3) . . . . ? C12B C11B C21B C22B 179.20(17) . . . . ? C24B N21B C21B C11B -179.03(19) . . . . ? C24B N21B C21B C22B 2.0(2) . . . . ? C51B N22B C22B C21B -176.69(16) . . . . ? B1B N22B C22B C21B 1.8(3) . . . . ? C51B N22B C22B C23B 3.0(3) . . . . ? B1B N22B C22B C23B -178.47(19) . . . . ? C11B C21B C22B N22B -0.5(3) . . . . ? N21B C21B C22B N22B 178.56(16) . . . . ? C11B C21B C22B C23B 179.78(17) . . . . ? N21B C21B C22B C23B -1.2(2) . . . . ? N22B C22B C23B C28B 1.7(4) . . . . ? C21B C22B C23B C28B -178.6(2) . . . . ? N22B C22B C23B C24B -179.78(19) . . . . ? C21B C22B C23B C24B -0.07(19) . . . . ? C21B N21B C24B C25B 178.27(19) . . . . ? C21B N21B C24B C23B -2.1(2) . . . . ? C28B C23B C24B N21B -179.90(16) . . . . ? C22B C23B C24B N21B 1.3(2) . . . . ? C28B C23B C24B C25B -0.2(3) . . . . ? C22B C23B C24B C25B -179.01(17) . . . . ? N21B C24B C25B C26B -179.62(18) . . . . ? C23B C24B C25B C26B 0.8(3) . . . . ? C24B C25B C26B C27B -0.5(3) . . . . ? C25B C26B C27B C28B -0.3(3) . . . . ? C26B C27B C28B C23B 0.9(3) . . . . ? C24B C23B C28B C27B -0.6(3) . . . . ? C22B C23B C28B C27B 177.74(19) . . . . ? C12B N12B C31B C36B -102.9(2) . . . . ? C12B N12B C31B C32B 82.4(2) . . . . ? C36B C31B C32B C33B 1.6(3) . . . . ? N12B C31B C32B C33B 175.99(17) . . . . ? C36B C31B C32B C37B -175.91(18) . . . . ? N12B C31B C32B C37B -1.5(3) . . . . ? C31B C32B C33B C34B -0.6(3) . . . . ? C37B C32B C33B C34B 176.8(2) . . . . ? C32B C33B C34B C35B -0.2(3) . . . . ? C33B C34B C35B C36B 0.2(3) . . . . ? C34B C35B C36B C31B 0.7(3) . . . . ? C34B C35B C36B C40B 179.6(2) . . . . ? C32B C31B C36B C35B -1.6(3) . . . . ? N12B C31B C36B C35B -176.11(17) . . . . ? C32B C31B C36B C40B 179.45(18) . . . . ? N12B C31B C36B C40B 5.0(3) . . . . ? C33B C32B C37B C38B 31.3(3) . . . . ? C31B C32B C37B C38B -151.3(2) . . . . ? C33B C32B C37B C39B -94.1(3) . . . . ? C31B C32B C37B C39B 83.3(2) . . . . ? C35B C36B C40B C42B 34.8(3) . . . . ? C31B C36B C40B C42B -146.33(19) . . . . ? C35B C36B C40B C41B -89.6(2) . . . . ? C31B C36B C40B C41B 89.2(2) . . . . ? C22B N22B C51B C52B 86.8(2) . . . . ? B1B N22B C51B C52B -91.8(2) . . . . ? C22B N22B C51B C56B -91.1(2) . . . . ? B1B N22B C51B C56B 90.3(2) . . . . ? C56B C51B C52B C53B -0.9(3) . . . . ? N22B C51B C52B C53B -178.71(16) . . . . ? C56B C51B C52B C57B 176.89(17) . . . . ? N22B C51B C52B C57B -0.9(3) . . . . ? C51B C52B C53B C54B 0.7(3) . . . . ? C57B C52B C53B C54B -177.13(18) . . . . ? C52B C53B C54B C55B -0.3(3) . . . . ? C53B C54B C55B C56B -0.1(3) . . . . ? C54B C55B C56B C51B 0.0(3) . . . . ? C54B C55B C56B C60B 178.34(18) . . . . ? C52B C51B C56B C55B 0.6(3) . . . . ? N22B C51B C56B C55B 178.36(16) . . . . ? C52B C51B C56B C60B -177.76(17) . . . . ? N22B C51B C56B C60B 0.0(3) . . . . ? C53B C52B C57B C59B -58.6(2) . . . . ? C51B C52B C57B C59B 123.7(2) . . . . ? C53B C52B C57B C58B 65.1(2) . . . . ? C51B C52B C57B C58B -112.6(2) . . . . ? C55B C56B C60B C61B -60.2(2) . . . . ? C51B C56B C60B C61B 118.1(2) . . . . ? C55B C56B C60B C62B 63.5(2) . . . . ? C51B C56B C60B C62B -118.2(2) . . . . ? C11B N11B B1B F2B -118.41(19) . . . . ? C14B N11B B1B F2B 63.0(2) . . . . ? C11B N11B B1B F1B 121.68(19) . . . . ? C14B N11B B1B F1B -56.9(2) . . . . ? C11B N11B B1B N22B 2.5(2) . . . . ? C14B N11B B1B N22B -176.10(16) . . . . ? C22B N22B B1B F2B 118.63(18) . . . . ? C51B N22B B1B F2B -62.8(2) . . . . ? C22B N22B B1B F1B -122.21(18) . . . . ? C51B N22B B1B F1B 56.3(2) . . . . ? C22B N22B B1B N11B -2.6(2) . . . . ? C51B N22B B1B N11B 175.90(15) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.75 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.387 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.048 # Attachment '- 2e.cif' data_vic1118 _database_code_depnum_ccdc_archive 'CCDC 895628' #TrackingRef '- 2e.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H35 B F2 N4' _chemical_formula_sum 'C36 H35 B F2 N4' _chemical_formula_weight 572.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 15.7903(6) _cell_length_b 11.9086(5) _cell_length_c 15.8933(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.4690(5) _cell_angle_gamma 90.00 _cell_volume 2979.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7647 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 23.41 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9685 _exptl_absorpt_correction_T_max 0.9923 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 23713 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 26.52 _reflns_number_total 6169 _reflns_number_gt 4522 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXD (Schneider & Sheldrick, 2002)' _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^)+(0.0481P)^2^+0.8099P] 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 6169 _refine_ls_number_parameters 388 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1059 _refine_ls_wR_factor_gt 0.0938 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 F1 F 0.17694(6) 0.02029(8) 0.64687(5) 0.0351(2) Uani 1 1 d . . . F2 F 0.25239(6) 0.18075(9) 0.63348(6) 0.0385(2) Uani 1 1 d . . . N11 N 0.18487(8) 0.09715(10) 0.50729(8) 0.0246(3) Uani 1 1 d . . . N12 N 0.07896(8) 0.04138(10) 0.30770(7) 0.0252(3) Uani 1 1 d . . . N21 N -0.04195(8) 0.12523(11) 0.43426(8) 0.0263(3) Uani 1 1 d . . . H21N H -0.0542 0.0965 0.3838 0.032 Uiso 1 1 calc R . . N22 N 0.09925(8) 0.19023(10) 0.61217(7) 0.0241(3) Uani 1 1 d . . . C11 C 0.11393(9) 0.08873(12) 0.45310(9) 0.0232(3) Uani 1 1 d . . . C12 C 0.13693(9) 0.05531(12) 0.36835(9) 0.0231(3) Uani 1 1 d . . . C13 C 0.23068(9) 0.05467(12) 0.37583(9) 0.0245(3) Uani 1 1 d . . . C14 C 0.25621(9) 0.07887(12) 0.46056(9) 0.0241(3) Uani 1 1 d . . . C15 C 0.34098(10) 0.08675(14) 0.48944(10) 0.0300(4) Uani 1 1 d . . . H15 H 0.3576 0.1004 0.5473 0.036 Uiso 1 1 calc R . . C16 C 0.40061(10) 0.07387(14) 0.43064(11) 0.0329(4) Uani 1 1 d . . . H16 H 0.4592 0.0796 0.4486 0.039 Uiso 1 1 calc R . . C17 C 0.37693(10) 0.05286(14) 0.34597(11) 0.0332(4) Uani 1 1 d . . . H17 H 0.4194 0.0460 0.3071 0.040 Uiso 1 1 calc R . . C18 C 0.29212(10) 0.04176(13) 0.31782(10) 0.0296(4) Uani 1 1 d . . . H18 H 0.2760 0.0257 0.2602 0.036 Uiso 1 1 calc R . . C21 C 0.03698(9) 0.12241(13) 0.47897(9) 0.0238(3) Uani 1 1 d . . . C22 C 0.03102(9) 0.17885(12) 0.55800(9) 0.0232(3) Uani 1 1 d . . . C23 C -0.05517(9) 0.21870(12) 0.55835(9) 0.0248(3) Uani 1 1 d . . . C24 C -0.09781(9) 0.18036(12) 0.48201(9) 0.0252(3) Uani 1 1 d . . . C25 C -0.18393(10) 0.20199(13) 0.46222(10) 0.0305(4) Uani 1 1 d . . . H25 H -0.2127 0.1747 0.4116 0.037 Uiso 1 1 calc R . . C26 C -0.22541(10) 0.26440(14) 0.51894(11) 0.0353(4) Uani 1 1 d . . . H26 H -0.2840 0.2806 0.5068 0.042 Uiso 1 1 calc R . . C27 C -0.18420(11) 0.30492(14) 0.59415(11) 0.0356(4) Uani 1 1 d . . . H27 H -0.2151 0.3485 0.6314 0.043 Uiso 1 1 calc R . . C28 C -0.09955(10) 0.28243(14) 0.61474(10) 0.0304(4) Uani 1 1 d . . . H28 H -0.0718 0.3095 0.6660 0.037 Uiso 1 1 calc R . . C31 C 0.10203(9) 0.01026(13) 0.22594(9) 0.0258(3) Uani 1 1 d . . . C32 C 0.07976(9) 0.07954(14) 0.15562(9) 0.0282(3) Uani 1 1 d . . . C33 C 0.10046(11) 0.03795(16) 0.07752(10) 0.0382(4) Uani 1 1 d . . . H33 H 0.0868 0.0822 0.0286 0.046 Uiso 1 1 calc R . . C34 C 0.13990(12) -0.06445(16) 0.06817(11) 0.0424(5) Uani 1 1 d . . . H34 H 0.1532 -0.0888 0.0138 0.051 Uiso 1 1 calc R . . C35 C 0.15991(12) -0.13118(15) 0.13770(11) 0.0403(4) Uani 1 1 d . . . H35 H 0.1865 -0.2020 0.1317 0.048 Uiso 1 1 calc R . . C36 C 0.14077(11) -0.09355(14) 0.21621(10) 0.0335(4) Uani 1 1 d . . . H36 H 0.1543 -0.1392 0.2644 0.040 Uiso 1 1 calc R . . C37 C 0.03530(10) 0.19314(15) 0.16430(10) 0.0348(4) Uani 1 1 d . . . C38 C -0.05595(11) 0.17282(19) 0.18874(12) 0.0503(5) Uani 1 1 d . . . H38A H -0.0542 0.1309 0.2419 0.060 Uiso 1 1 calc R . . H38B H -0.0875 0.1295 0.1442 0.060 Uiso 1 1 calc R . . H38C H -0.0842 0.2451 0.1956 0.060 Uiso 1 1 calc R . . C39 C 0.08397(14) 0.26884(16) 0.23013(13) 0.0499(5) Uani 1 1 d . . . H39A H 0.0898 0.2301 0.2847 0.060 Uiso 1 1 calc R . . H39B H 0.0526 0.3391 0.2358 0.060 Uiso 1 1 calc R . . H39C H 0.1404 0.2855 0.2118 0.060 Uiso 1 1 calc R . . C40 C 0.02898(12) 0.25884(18) 0.08087(12) 0.0480(5) Uani 1 1 d . . . H40A H 0.0862 0.2747 0.0641 0.058 Uiso 1 1 calc R . . H40B H -0.0011 0.3297 0.0883 0.058 Uiso 1 1 calc R . . H40C H -0.0022 0.2141 0.0369 0.058 Uiso 1 1 calc R . . C41 C 0.09561(9) 0.25187(13) 0.69029(9) 0.0247(3) Uani 1 1 d . . . C42 C 0.11749(9) 0.36534(13) 0.69914(10) 0.0268(3) Uani 1 1 d . . . C43 C 0.11931(10) 0.40733(15) 0.78207(10) 0.0344(4) Uani 1 1 d . . . H43 H 0.1346 0.4837 0.7916 0.041 Uiso 1 1 calc R . . C44 C 0.10000(10) 0.34328(16) 0.85010(10) 0.0373(4) Uani 1 1 d . . . H44 H 0.1033 0.3753 0.9050 0.045 Uiso 1 1 calc R . . C45 C 0.07581(11) 0.23274(16) 0.83866(10) 0.0376(4) Uani 1 1 d . . . H45 H 0.0602 0.1889 0.8849 0.045 Uiso 1 1 calc R . . C46 C 0.07473(10) 0.18685(15) 0.75877(10) 0.0322(4) Uani 1 1 d . . . H46 H 0.0596 0.1102 0.7503 0.039 Uiso 1 1 calc R . . C47 C 0.13888(10) 0.44912(13) 0.62965(10) 0.0324(4) Uani 1 1 d . . . C48 C 0.22804(12) 0.49579(18) 0.65130(13) 0.0501(5) Uani 1 1 d . . . H48A H 0.2320 0.5257 0.7089 0.060 Uiso 1 1 calc R . . H48B H 0.2394 0.5560 0.6117 0.060 Uiso 1 1 calc R . . H48C H 0.2699 0.4356 0.6472 0.060 Uiso 1 1 calc R . . C49 C 0.07363(14) 0.54527(18) 0.62794(16) 0.0612(6) Uani 1 1 d . . . H49A H 0.0727 0.5775 0.6846 0.073 Uiso 1 1 calc R . . H49B H 0.0172 0.5160 0.6096 0.073 Uiso 1 1 calc R . . H49C H 0.0895 0.6035 0.5885 0.073 Uiso 1 1 calc R . . C50 C 0.13615(15) 0.40371(17) 0.53946(11) 0.0531(6) Uani 1 1 d . . . H50A H 0.1508 0.4639 0.5011 0.064 Uiso 1 1 calc R . . H50B H 0.0789 0.3760 0.5226 0.064 Uiso 1 1 calc R . . H50C H 0.1770 0.3421 0.5369 0.064 Uiso 1 1 calc R . . B B 0.18201(11) 0.12132(15) 0.60211(11) 0.0263(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0424(6) 0.0386(5) 0.0234(5) 0.0030(4) -0.0030(4) 0.0088(4) F2 0.0246(5) 0.0543(6) 0.0358(5) -0.0161(5) -0.0032(4) -0.0040(4) N11 0.0217(6) 0.0302(7) 0.0216(6) -0.0011(5) -0.0002(5) 0.0003(5) N12 0.0280(7) 0.0275(7) 0.0200(6) 0.0001(5) 0.0011(5) -0.0004(5) N21 0.0228(7) 0.0351(7) 0.0206(6) -0.0022(5) -0.0017(5) 0.0003(5) N22 0.0243(7) 0.0286(7) 0.0191(6) -0.0017(5) 0.0006(5) -0.0013(5) C11 0.0234(8) 0.0246(8) 0.0210(7) 0.0010(6) -0.0012(6) -0.0009(6) C12 0.0267(8) 0.0210(7) 0.0216(7) 0.0018(6) 0.0021(6) 0.0002(6) C13 0.0261(8) 0.0235(8) 0.0240(8) 0.0017(6) 0.0014(6) -0.0003(6) C14 0.0245(8) 0.0237(7) 0.0243(8) 0.0006(6) 0.0037(6) 0.0012(6) C15 0.0258(8) 0.0358(9) 0.0279(8) -0.0004(7) -0.0011(7) 0.0008(7) C16 0.0233(8) 0.0359(9) 0.0394(10) -0.0018(7) 0.0018(7) 0.0002(7) C17 0.0295(9) 0.0359(9) 0.0352(9) -0.0023(7) 0.0094(7) 0.0014(7) C18 0.0327(9) 0.0307(9) 0.0259(8) -0.0018(6) 0.0056(7) -0.0002(7) C21 0.0240(8) 0.0265(8) 0.0204(7) 0.0011(6) -0.0011(6) -0.0014(6) C22 0.0244(8) 0.0237(7) 0.0216(7) 0.0019(6) 0.0023(6) -0.0032(6) C23 0.0243(8) 0.0256(8) 0.0244(8) 0.0034(6) 0.0015(6) -0.0005(6) C24 0.0256(8) 0.0245(8) 0.0256(8) 0.0039(6) 0.0021(6) -0.0005(6) C25 0.0236(8) 0.0341(9) 0.0331(9) 0.0021(7) -0.0016(7) -0.0014(7) C26 0.0241(8) 0.0389(10) 0.0427(10) 0.0038(8) 0.0023(7) 0.0034(7) C27 0.0318(9) 0.0394(10) 0.0365(9) -0.0018(8) 0.0084(7) 0.0060(7) C28 0.0310(9) 0.0336(9) 0.0272(8) -0.0003(7) 0.0056(7) -0.0003(7) C31 0.0253(8) 0.0314(8) 0.0206(7) -0.0023(6) 0.0013(6) -0.0056(6) C32 0.0217(8) 0.0388(9) 0.0236(8) 0.0017(7) -0.0007(6) -0.0057(7) C33 0.0365(10) 0.0544(12) 0.0235(8) 0.0035(8) 0.0004(7) -0.0080(8) C34 0.0470(11) 0.0528(12) 0.0282(9) -0.0125(8) 0.0083(8) -0.0097(9) C35 0.0455(11) 0.0359(10) 0.0407(10) -0.0115(8) 0.0108(8) -0.0057(8) C36 0.0403(10) 0.0320(9) 0.0285(9) -0.0015(7) 0.0039(7) -0.0029(7) C37 0.0294(9) 0.0433(10) 0.0316(9) 0.0100(7) 0.0017(7) 0.0048(7) C38 0.0342(10) 0.0738(14) 0.0436(11) 0.0186(10) 0.0069(8) 0.0107(10) C39 0.0631(13) 0.0308(10) 0.0542(12) 0.0053(9) -0.0052(10) 0.0065(9) C40 0.0425(11) 0.0597(13) 0.0421(11) 0.0231(9) 0.0051(9) 0.0129(9) C41 0.0222(7) 0.0316(8) 0.0201(7) -0.0020(6) -0.0003(6) 0.0008(6) C42 0.0214(7) 0.0325(8) 0.0261(8) -0.0015(7) -0.0009(6) 0.0024(6) C43 0.0299(9) 0.0387(10) 0.0342(9) -0.0117(7) 0.0000(7) 0.0016(7) C44 0.0297(9) 0.0587(12) 0.0235(8) -0.0115(8) 0.0012(7) 0.0030(8) C45 0.0352(9) 0.0551(11) 0.0228(8) 0.0047(8) 0.0048(7) 0.0000(8) C46 0.0328(9) 0.0376(9) 0.0262(8) 0.0011(7) 0.0031(7) -0.0025(7) C47 0.0328(9) 0.0296(9) 0.0339(9) 0.0027(7) -0.0033(7) -0.0026(7) C48 0.0401(11) 0.0625(13) 0.0468(11) 0.0099(10) -0.0015(9) -0.0163(9) C49 0.0558(13) 0.0462(12) 0.0820(16) 0.0222(11) 0.0087(12) 0.0116(10) C50 0.0812(15) 0.0466(12) 0.0305(10) 0.0109(8) -0.0019(10) -0.0220(11) B 0.0241(9) 0.0330(10) 0.0212(9) -0.0035(7) -0.0023(7) -0.0008(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 B 1.403(2) . ? F2 B 1.3777(19) . ? N11 C11 1.3625(18) . ? N11 C14 1.4136(19) . ? N11 B 1.538(2) . ? N12 C12 1.2871(18) . ? N12 C31 1.4257(19) . ? N21 C24 1.3745(19) . ? N21 C21 1.3861(18) . ? N22 C22 1.3327(18) . ? N22 C41 1.4474(18) . ? N22 B 1.562(2) . ? C11 C21 1.373(2) . ? C11 C12 1.477(2) . ? C12 C13 1.476(2) . ? C13 C18 1.398(2) . ? C13 C14 1.405(2) . ? C14 C15 1.384(2) . ? C15 C16 1.386(2) . ? C16 C17 1.391(2) . ? C17 C18 1.385(2) . ? C21 C22 1.434(2) . ? C22 C23 1.442(2) . ? C23 C28 1.403(2) . ? C23 C24 1.417(2) . ? C24 C25 1.396(2) . ? C25 C26 1.373(2) . ? C26 C27 1.401(2) . ? C27 C28 1.377(2) . ? C31 C36 1.393(2) . ? C31 C32 1.411(2) . ? C32 C33 1.399(2) . ? C32 C37 1.535(2) . ? C33 C34 1.383(3) . ? C34 C35 1.378(3) . ? C35 C36 1.381(2) . ? C37 C40 1.536(2) . ? C37 C39 1.540(3) . ? C37 C38 1.540(2) . ? C41 C46 1.396(2) . ? C41 C42 1.399(2) . ? C42 C43 1.408(2) . ? C42 C47 1.545(2) . ? C43 C44 1.377(2) . ? C44 C45 1.379(3) . ? C45 C46 1.381(2) . ? C47 C48 1.528(2) . ? C47 C50 1.529(2) . ? C47 C49 1.539(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 C11 N11 C14 107.82(12) . . ? C11 N11 B 123.20(12) . . ? C14 N11 B 128.97(12) . . ? C12 N12 C31 119.92(13) . . ? C24 N21 C21 108.58(12) . . ? C22 N22 C41 121.44(12) . . ? C22 N22 B 121.41(12) . . ? C41 N22 B 116.35(11) . . ? N11 C11 C21 119.51(13) . . ? N11 C11 C12 110.36(12) . . ? C21 C11 C12 129.66(13) . . ? N12 C12 C13 135.23(14) . . ? N12 C12 C11 120.45(13) . . ? C13 C12 C11 104.14(12) . . ? C18 C13 C14 119.51(14) . . ? C18 C13 C12 133.69(14) . . ? C14 C13 C12 106.69(13) . . ? C15 C14 C13 121.98(14) . . ? C15 C14 N11 127.23(14) . . ? C13 C14 N11 110.75(13) . . ? C14 C15 C16 117.34(15) . . ? C15 C16 C17 121.79(15) . . ? C18 C17 C16 120.66(15) . . ? C17 C18 C13 118.68(15) . . ? C11 C21 N21 129.43(14) . . ? C11 C21 C22 121.29(13) . . ? N21 C21 C22 108.65(13) . . ? N22 C22 C21 120.57(13) . . ? N22 C22 C23 132.84(14) . . ? C21 C22 C23 106.51(12) . . ? C28 C23 C24 119.59(14) . . ? C28 C23 C22 134.37(14) . . ? C24 C23 C22 106.05(13) . . ? N21 C24 C25 128.29(14) . . ? N21 C24 C23 110.13(13) . . ? C25 C24 C23 121.56(14) . . ? C26 C25 C24 117.26(15) . . ? C25 C26 C27 122.19(15) . . ? C28 C27 C26 120.88(16) . . ? C27 C28 C23 118.50(15) . . ? C36 C31 C32 121.02(14) . . ? C36 C31 N12 118.52(14) . . ? C32 C31 N12 120.28(14) . . ? C33 C32 C31 115.77(15) . . ? C33 C32 C37 122.13(14) . . ? C31 C32 C37 122.10(14) . . ? C34 C33 C32 123.10(16) . . ? C35 C34 C33 119.97(16) . . ? C34 C35 C36 119.00(17) . . ? C35 C36 C31 121.13(16) . . ? C32 C37 C40 111.76(14) . . ? C32 C37 C39 111.67(13) . . ? C40 C37 C39 106.48(15) . . ? C32 C37 C38 109.12(15) . . ? C40 C37 C38 107.37(14) . . ? C39 C37 C38 110.34(16) . . ? C46 C41 C42 121.93(14) . . ? C46 C41 N22 114.53(13) . . ? C42 C41 N22 123.37(13) . . ? C41 C42 C43 115.08(15) . . ? C41 C42 C47 128.16(14) . . ? C43 C42 C47 116.75(14) . . ? C44 C43 C42 123.29(16) . . ? C43 C44 C45 120.10(15) . . ? C44 C45 C46 118.84(16) . . ? C45 C46 C41 120.70(16) . . ? C48 C47 C50 107.33(16) . . ? C48 C47 C49 109.70(16) . . ? C50 C47 C49 106.06(16) . . ? C48 C47 C42 108.83(13) . . ? C50 C47 C42 116.73(14) . . ? C49 C47 C42 108.04(15) . . ? F2 B F1 109.47(13) . . ? F2 B N11 111.48(13) . . ? F1 B N11 110.09(13) . . ? F2 B N22 110.53(13) . . ? F1 B N22 108.50(13) . . ? N11 B N22 106.70(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 N11 C11 C21 -168.48(13) . . . . ? B N11 C11 C21 12.1(2) . . . . ? C14 N11 C11 C12 4.40(16) . . . . ? B N11 C11 C12 -175.01(13) . . . . ? C31 N12 C12 C13 5.2(3) . . . . ? C31 N12 C12 C11 179.35(13) . . . . ? N11 C11 C12 N12 179.25(13) . . . . ? C21 C11 C12 N12 -8.8(2) . . . . ? N11 C11 C12 C13 -5.00(16) . . . . ? C21 C11 C12 C13 166.94(15) . . . . ? N12 C12 C13 C18 2.4(3) . . . . ? C11 C12 C13 C18 -172.41(16) . . . . ? N12 C12 C13 C14 178.40(16) . . . . ? C11 C12 C13 C14 3.60(15) . . . . ? C18 C13 C14 C15 -2.2(2) . . . . ? C12 C13 C14 C15 -178.90(14) . . . . ? C18 C13 C14 N11 175.50(13) . . . . ? C12 C13 C14 N11 -1.18(16) . . . . ? C11 N11 C14 C15 175.57(15) . . . . ? B N11 C14 C15 -5.1(3) . . . . ? C11 N11 C14 C13 -2.00(17) . . . . ? B N11 C14 C13 177.37(14) . . . . ? C13 C14 C15 C16 2.3(2) . . . . ? N11 C14 C15 C16 -174.99(15) . . . . ? C14 C15 C16 C17 -0.6(2) . . . . ? C15 C16 C17 C18 -1.3(3) . . . . ? C16 C17 C18 C13 1.5(2) . . . . ? C14 C13 C18 C17 0.3(2) . . . . ? C12 C13 C18 C17 175.87(16) . . . . ? N11 C11 C21 N21 177.46(14) . . . . ? C12 C11 C21 N21 6.1(3) . . . . ? N11 C11 C21 C22 7.7(2) . . . . ? C12 C11 C21 C22 -163.65(14) . . . . ? C24 N21 C21 C11 -171.28(15) . . . . ? C24 N21 C21 C22 -0.47(16) . . . . ? C41 N22 C22 C21 176.78(13) . . . . ? B N22 C22 C21 -13.8(2) . . . . ? C41 N22 C22 C23 0.7(2) . . . . ? B N22 C22 C23 170.15(15) . . . . ? C11 C21 C22 N22 -6.6(2) . . . . ? N21 C21 C22 N22 -178.34(13) . . . . ? C11 C21 C22 C23 170.33(14) . . . . ? N21 C21 C22 C23 -1.37(16) . . . . ? N22 C22 C23 C28 -0.6(3) . . . . ? C21 C22 C23 C28 -177.06(17) . . . . ? N22 C22 C23 C24 179.05(16) . . . . ? C21 C22 C23 C24 2.61(16) . . . . ? C21 N21 C24 C25 -179.54(15) . . . . ? C21 N21 C24 C23 2.20(17) . . . . ? C28 C23 C24 N21 176.73(14) . . . . ? C22 C23 C24 N21 -3.00(16) . . . . ? C28 C23 C24 C25 -1.7(2) . . . . ? C22 C23 C24 C25 178.60(14) . . . . ? N21 C24 C25 C26 -176.59(15) . . . . ? C23 C24 C25 C26 1.5(2) . . . . ? C24 C25 C26 C27 -0.3(2) . . . . ? C25 C26 C27 C28 -0.7(3) . . . . ? C26 C27 C28 C23 0.5(2) . . . . ? C24 C23 C28 C27 0.6(2) . . . . ? C22 C23 C28 C27 -179.74(16) . . . . ? C12 N12 C31 C36 64.03(19) . . . . ? C12 N12 C31 C32 -120.94(16) . . . . ? C36 C31 C32 C33 -1.1(2) . . . . ? N12 C31 C32 C33 -175.99(14) . . . . ? C36 C31 C32 C37 178.66(15) . . . . ? N12 C31 C32 C37 3.8(2) . . . . ? C31 C32 C33 C34 0.3(2) . . . . ? C37 C32 C33 C34 -179.50(16) . . . . ? C32 C33 C34 C35 0.6(3) . . . . ? C33 C34 C35 C36 -0.7(3) . . . . ? C34 C35 C36 C31 -0.2(3) . . . . ? C32 C31 C36 C35 1.1(2) . . . . ? N12 C31 C36 C35 176.07(14) . . . . ? C33 C32 C37 C40 -8.0(2) . . . . ? C31 C32 C37 C40 172.30(15) . . . . ? C33 C32 C37 C39 -127.12(17) . . . . ? C31 C32 C37 C39 53.1(2) . . . . ? C33 C32 C37 C38 110.63(17) . . . . ? C31 C32 C37 C38 -69.11(19) . . . . ? C22 N22 C41 C46 90.19(17) . . . . ? B N22 C41 C46 -79.72(17) . . . . ? C22 N22 C41 C42 -94.61(18) . . . . ? B N22 C41 C42 95.48(17) . . . . ? C46 C41 C42 C43 1.8(2) . . . . ? N22 C41 C42 C43 -173.00(13) . . . . ? C46 C41 C42 C47 -177.60(15) . . . . ? N22 C41 C42 C47 7.5(2) . . . . ? C41 C42 C43 C44 -0.9(2) . . . . ? C47 C42 C43 C44 178.62(15) . . . . ? C42 C43 C44 C45 -1.3(3) . . . . ? C43 C44 C45 C46 2.6(2) . . . . ? C44 C45 C46 C41 -1.6(2) . . . . ? C42 C41 C46 C45 -0.6(2) . . . . ? N22 C41 C46 C45 174.64(14) . . . . ? C41 C42 C47 C48 -121.66(18) . . . . ? C43 C42 C47 C48 58.90(19) . . . . ? C41 C42 C47 C50 -0.1(2) . . . . ? C43 C42 C47 C50 -179.49(15) . . . . ? C41 C42 C47 C49 119.27(19) . . . . ? C43 C42 C47 C49 -60.17(19) . . . . ? C11 N11 B F2 -148.84(14) . . . . ? C14 N11 B F2 31.9(2) . . . . ? C11 N11 B F1 89.47(17) . . . . ? C14 N11 B F1 -89.81(18) . . . . ? C11 N11 B N22 -28.08(19) . . . . ? C14 N11 B N22 152.64(14) . . . . ? C22 N22 B F2 149.98(13) . . . . ? C41 N22 B F2 -40.11(18) . . . . ? C22 N22 B F1 -89.98(16) . . . . ? C41 N22 B F1 79.93(15) . . . . ? C22 N22 B N11 28.60(19) . . . . ? C41 N22 B N11 -161.48(12) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.52 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.201 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.040 # Attachment '- 2f.cif' data_vic1241 _database_code_depnum_ccdc_archive 'CCDC 895629' #TrackingRef '- 2f.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H17 B Cl2 F2 N4, 0.5(C H2 Cl2)' _chemical_formula_sum 'C28.5 H18 B Cl3 F2 N4' _chemical_formula_weight 571.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'I 2/a' _symmetry_space_group_name_Hall '-I 2ya' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 14.0731(2) _cell_length_b 11.5359(2) _cell_length_c 31.2056(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.7226(5) _cell_angle_gamma 90.00 _cell_volume 5055.41(13) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9856 _cell_measurement_theta_min 4.96 _cell_measurement_theta_max 69.56 _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2328 _exptl_absorpt_coefficient_mu 3.643 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.3538 _exptl_absorpt_correction_T_max 0.7950 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16710 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 4.09 _diffrn_reflns_theta_max 70.07 _reflns_number_total 4749 _reflns_number_gt 4450 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXD (Schneider & Sheldrick, 2002)' _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^)+(0.0564P)^2^+4.0662P] 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 4749 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.1009 _refine_ls_wR_factor_gt 0.0989 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 Cl1 Cl -0.10787(4) 0.18550(5) -0.024023(14) 0.06132(16) Uani 1 1 d . . . Cl2 Cl 0.40029(4) 0.03193(6) 0.475280(16) 0.06823(18) Uani 1 1 d . . . F1 F 0.18851(7) -0.14616(8) 0.29890(3) 0.0416(2) Uani 1 1 d . . . F2 F 0.04056(7) -0.07981(8) 0.31055(3) 0.0385(2) Uani 1 1 d . . . N11 N 0.10421(8) -0.03678(10) 0.24222(4) 0.0260(2) Uani 1 1 d . . . N12 N 0.02429(9) 0.15331(10) 0.15954(4) 0.0289(3) Uani 1 1 d . . . N21 N 0.09767(9) 0.28156(10) 0.23634(4) 0.0268(2) Uani 1 1 d . . . H21N H 0.0572(15) 0.3053(17) 0.2167(7) 0.045(5) Uiso 1 1 d . . . N22 N 0.16842(8) 0.05922(10) 0.31031(4) 0.0262(2) Uani 1 1 d . . . C11 C 0.08715(9) 0.06955(12) 0.22515(4) 0.0257(3) Uani 1 1 d . . . C12 C 0.05185(9) 0.06067(12) 0.17963(4) 0.0259(3) Uani 1 1 d . . . C13 C 0.05459(10) -0.06450(12) 0.17056(4) 0.0270(3) Uani 1 1 d . . . C14 C 0.08728(9) -0.11918(12) 0.20907(4) 0.0267(3) Uani 1 1 d . . . C15 C 0.09916(11) -0.23802(13) 0.21187(5) 0.0320(3) Uani 1 1 d . . . H15 H 0.1223 -0.2739 0.2379 0.038 Uiso 1 1 calc R . . C16 C 0.07592(12) -0.30288(14) 0.17509(5) 0.0377(4) Uani 1 1 d . . . H16 H 0.0837 -0.3847 0.1760 0.045 Uiso 1 1 calc R . . C17 C 0.04161(12) -0.25086(14) 0.13698(5) 0.0376(3) Uani 1 1 d . . . H17 H 0.0256 -0.2976 0.1125 0.045 Uiso 1 1 calc R . . C18 C 0.03046(11) -0.13178(13) 0.13426(5) 0.0323(3) Uani 1 1 d . . . H18 H 0.0068 -0.0965 0.1082 0.039 Uiso 1 1 calc R . . C21 C 0.10683(10) 0.16747(12) 0.24908(4) 0.0253(3) Uani 1 1 d . . . C22 C 0.15221(9) 0.16234(12) 0.29120(4) 0.0253(3) Uani 1 1 d . . . C23 C 0.17120(9) 0.28062(12) 0.30399(4) 0.0255(3) Uani 1 1 d . . . C24 C 0.13530(9) 0.35025(12) 0.26907(4) 0.0257(3) Uani 1 1 d . . . C25 C 0.14163(10) 0.47114(13) 0.27003(5) 0.0294(3) Uani 1 1 d . . . H25 H 0.1189 0.5167 0.2461 0.035 Uiso 1 1 calc R . . C26 C 0.18186(10) 0.52200(13) 0.30678(5) 0.0314(3) Uani 1 1 d . . . H26 H 0.1875 0.6040 0.3081 0.038 Uiso 1 1 calc R . . C27 C 0.21471(10) 0.45499(13) 0.34236(5) 0.0320(3) Uani 1 1 d . . . H27 H 0.2404 0.4927 0.3676 0.038 Uiso 1 1 calc R . . C28 C 0.21035(10) 0.33582(13) 0.34129(5) 0.0291(3) Uani 1 1 d . . . H28 H 0.2334 0.2914 0.3654 0.035 Uiso 1 1 calc R . . C31 C -0.00742(10) 0.15305(12) 0.11567(5) 0.0293(3) Uani 1 1 d . . . C32 C 0.04853(11) 0.11305(14) 0.08378(5) 0.0347(3) Uani 1 1 d . . . H32 H 0.1085 0.0784 0.0915 0.042 Uiso 1 1 calc R . . C33 C 0.01786(12) 0.12312(14) 0.04082(5) 0.0383(4) Uani 1 1 d . . . H33 H 0.0567 0.0962 0.0191 0.046 Uiso 1 1 calc R . . C34 C -0.06960(13) 0.17261(15) 0.02998(5) 0.0397(4) Uani 1 1 d . . . C35 C -0.12661(12) 0.21372(15) 0.06129(5) 0.0415(4) Uani 1 1 d . . . H35 H -0.1870 0.2470 0.0535 0.050 Uiso 1 1 calc R . . C36 C -0.09451(11) 0.20574(14) 0.10411(5) 0.0351(3) Uani 1 1 d . . . H36 H -0.1320 0.2363 0.1257 0.042 Uiso 1 1 calc R . . C41 C 0.22358(10) 0.05329(12) 0.35055(4) 0.0270(3) Uani 1 1 d . . . C42 C 0.31774(11) 0.08787(14) 0.35296(5) 0.0337(3) Uani 1 1 d . . . H42 H 0.3451 0.1165 0.3280 0.040 Uiso 1 1 calc R . . C43 C 0.37268(11) 0.08126(14) 0.39132(5) 0.0377(3) Uani 1 1 d . . . H43 H 0.4374 0.1053 0.3930 0.045 Uiso 1 1 calc R . . C44 C 0.33163(13) 0.03910(15) 0.42692(5) 0.0416(4) Uani 1 1 d . . . C45 C 0.23780(14) 0.00319(19) 0.42510(6) 0.0521(5) Uani 1 1 d . . . H45 H 0.2108 -0.0262 0.4500 0.062 Uiso 1 1 calc R . . C46 C 0.18357(12) 0.01043(16) 0.38659(5) 0.0420(4) Uani 1 1 d . . . H46 H 0.1190 -0.0140 0.3849 0.050 Uiso 1 1 calc R . . B B 0.12632(12) -0.05596(14) 0.29090(5) 0.0287(3) Uani 1 1 d . . . Cl1S Cl 0.1995(3) 0.1506(3) -0.04269(14) 0.1083(13) Uani 0.50 1 d P A -1 Cl2S Cl 0.2940(3) 0.1011(3) 0.04029(12) 0.0802(8) Uani 0.50 1 d P A -1 C1S C 0.244(3) 0.2073(4) 0.0035(15) 0.083(4) Uani 0.50 1 d P A -1 H1SA H 0.1921 0.2490 0.0172 0.100 Uiso 0.50 1 calc PR A -1 H1SB H 0.2933 0.2646 -0.0026 0.100 Uiso 0.50 1 calc PR A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0773(3) 0.0761(4) 0.0283(2) 0.00108(19) -0.0144(2) 0.0154(3) Cl2 0.0728(4) 0.0848(4) 0.0426(3) 0.0039(2) -0.0303(2) 0.0036(3) F1 0.0558(6) 0.0272(5) 0.0395(5) -0.0005(4) -0.0151(4) 0.0095(4) F2 0.0442(5) 0.0425(5) 0.0285(4) -0.0004(4) 0.0001(4) -0.0170(4) N11 0.0290(6) 0.0223(6) 0.0263(6) -0.0008(4) -0.0012(4) 0.0007(4) N12 0.0317(6) 0.0283(6) 0.0261(6) 0.0008(5) -0.0022(5) 0.0014(5) N21 0.0314(6) 0.0237(6) 0.0247(6) 0.0011(4) -0.0023(5) 0.0025(5) N22 0.0294(6) 0.0243(6) 0.0244(6) 0.0021(4) -0.0025(4) -0.0007(4) C11 0.0253(6) 0.0266(7) 0.0250(7) 0.0007(5) 0.0007(5) 0.0013(5) C12 0.0250(6) 0.0276(7) 0.0251(7) -0.0010(5) 0.0011(5) -0.0004(5) C13 0.0278(7) 0.0257(7) 0.0275(7) -0.0007(5) 0.0020(5) -0.0004(5) C14 0.0258(7) 0.0278(7) 0.0265(7) -0.0021(5) 0.0013(5) -0.0008(5) C15 0.0370(7) 0.0265(7) 0.0324(7) -0.0003(6) 0.0000(6) 0.0017(6) C16 0.0481(9) 0.0258(8) 0.0393(8) -0.0043(6) 0.0024(7) 0.0017(6) C17 0.0492(9) 0.0314(8) 0.0320(8) -0.0079(6) 0.0016(6) -0.0021(7) C18 0.0384(8) 0.0325(8) 0.0259(7) -0.0023(6) 0.0008(6) -0.0016(6) C21 0.0268(6) 0.0242(7) 0.0247(7) 0.0011(5) 0.0002(5) 0.0014(5) C22 0.0245(6) 0.0258(7) 0.0256(7) 0.0004(5) 0.0014(5) 0.0004(5) C23 0.0249(6) 0.0249(7) 0.0268(7) 0.0006(5) 0.0015(5) 0.0002(5) C24 0.0251(6) 0.0250(7) 0.0272(7) -0.0002(5) 0.0021(5) 0.0007(5) C25 0.0302(7) 0.0251(7) 0.0331(7) 0.0027(5) 0.0023(6) 0.0015(5) C26 0.0296(7) 0.0230(7) 0.0415(8) -0.0020(6) 0.0026(6) -0.0008(5) C27 0.0302(7) 0.0299(8) 0.0351(8) -0.0062(6) -0.0026(6) -0.0016(6) C28 0.0290(7) 0.0292(7) 0.0284(7) -0.0006(5) -0.0021(5) -0.0001(5) C31 0.0358(7) 0.0243(7) 0.0272(7) 0.0013(5) -0.0031(6) -0.0023(5) C32 0.0359(8) 0.0367(8) 0.0310(7) 0.0015(6) -0.0015(6) 0.0032(6) C33 0.0461(9) 0.0402(9) 0.0284(8) -0.0007(6) 0.0015(6) 0.0026(7) C34 0.0509(9) 0.0398(9) 0.0270(8) 0.0020(6) -0.0081(7) 0.0014(7) C35 0.0423(9) 0.0434(9) 0.0374(8) 0.0019(7) -0.0089(7) 0.0084(7) C36 0.0385(8) 0.0349(8) 0.0315(8) 0.0001(6) -0.0019(6) 0.0046(6) C41 0.0315(7) 0.0223(7) 0.0266(7) 0.0003(5) -0.0038(5) 0.0010(5) C42 0.0326(7) 0.0362(8) 0.0321(8) 0.0012(6) -0.0005(6) -0.0012(6) C43 0.0324(8) 0.0377(9) 0.0416(9) -0.0041(7) -0.0089(6) 0.0022(6) C44 0.0499(9) 0.0391(9) 0.0332(8) 0.0006(6) -0.0161(7) 0.0028(7) C45 0.0606(11) 0.0650(12) 0.0294(8) 0.0127(8) -0.0059(8) -0.0156(9) C46 0.0409(8) 0.0526(10) 0.0318(8) 0.0066(7) -0.0033(6) -0.0141(7) B 0.0352(8) 0.0234(8) 0.0266(8) 0.0013(6) -0.0038(6) -0.0016(6) Cl1S 0.0987(15) 0.176(4) 0.0509(10) 0.011(2) 0.0134(9) -0.006(2) Cl2S 0.0717(11) 0.1104(19) 0.0607(14) 0.0256(14) 0.0217(10) 0.0210(13) C1S 0.084(9) 0.065(3) 0.101(13) 0.008(8) 0.011(6) -0.018(8) _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 Cl1 C34 1.7420(16) . ? Cl2 C44 1.7403(16) . ? F1 B 1.3721(19) . ? F2 B 1.4157(19) . ? N11 C11 1.3526(18) . ? N11 C14 1.4138(18) . ? N11 B 1.5466(19) . ? N12 C12 1.2861(19) . ? N12 C31 1.4119(18) . ? N21 C24 1.3716(18) . ? N21 C21 1.3785(18) . ? N22 C22 1.3436(18) . ? N22 C41 1.4343(17) . ? N22 B 1.5610(19) . ? C11 C21 1.372(2) . ? C11 C12 1.4776(18) . ? C12 C13 1.4724(19) . ? C13 C18 1.397(2) . ? C13 C14 1.408(2) . ? C14 C15 1.383(2) . ? C15 C16 1.391(2) . ? C16 C17 1.390(2) . ? C17 C18 1.385(2) . ? C21 C22 1.4246(19) . ? C22 C23 1.4417(19) . ? C23 C28 1.407(2) . ? C23 C24 1.4200(19) . ? C24 C25 1.398(2) . ? C25 C26 1.377(2) . ? C26 C27 1.406(2) . ? C27 C28 1.376(2) . ? C31 C32 1.388(2) . ? C31 C36 1.394(2) . ? C32 C33 1.386(2) . ? C33 C34 1.379(2) . ? C34 C35 1.387(2) . ? C35 C36 1.386(2) . ? C41 C42 1.381(2) . ? C41 C46 1.381(2) . ? C42 C43 1.384(2) . ? C43 C44 1.374(3) . ? C44 C45 1.382(3) . ? C45 C46 1.384(2) . ? Cl1S C1S 1.66(5) . ? Cl2S C1S 1.79(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 C11 N11 C14 107.72(11) . . ? C11 N11 B 122.40(11) . . ? C14 N11 B 129.51(11) . . ? C12 N12 C31 122.49(12) . . ? C24 N21 C21 108.20(11) . . ? C22 N22 C41 119.84(11) . . ? C22 N22 B 122.15(11) . . ? C41 N22 B 117.99(11) . . ? N11 C11 C21 120.51(12) . . ? N11 C11 C12 110.84(12) . . ? C21 C11 C12 128.58(13) . . ? N12 C12 C13 137.05(13) . . ? N12 C12 C11 118.88(12) . . ? C13 C12 C11 103.97(11) . . ? C18 C13 C14 119.48(13) . . ? C18 C13 C12 133.85(13) . . ? C14 C13 C12 106.65(12) . . ? C15 C14 C13 121.98(13) . . ? C15 C14 N11 127.31(13) . . ? C13 C14 N11 110.71(12) . . ? C14 C15 C16 117.38(14) . . ? C17 C16 C15 121.57(15) . . ? C18 C17 C16 120.82(14) . . ? C17 C18 C13 118.75(14) . . ? C11 C21 N21 128.09(13) . . ? C11 C21 C22 122.03(13) . . ? N21 C21 C22 109.49(12) . . ? N22 C22 C21 119.95(12) . . ? N22 C22 C23 133.78(13) . . ? C21 C22 C23 106.26(12) . . ? C28 C23 C24 118.65(13) . . ? C28 C23 C22 135.46(13) . . ? C24 C23 C22 105.82(12) . . ? N21 C24 C25 127.85(13) . . ? N21 C24 C23 110.21(12) . . ? C25 C24 C23 121.93(13) . . ? C26 C25 C24 117.73(13) . . ? C25 C26 C27 121.31(14) . . ? C28 C27 C26 121.21(14) . . ? C27 C28 C23 119.10(14) . . ? C32 C31 C36 119.32(14) . . ? C32 C31 N12 122.53(13) . . ? C36 C31 N12 117.84(13) . . ? C33 C32 C31 120.68(14) . . ? C34 C33 C32 119.26(15) . . ? C33 C34 C35 121.10(15) . . ? C33 C34 Cl1 119.18(13) . . ? C35 C34 Cl1 119.71(13) . . ? C36 C35 C34 119.29(15) . . ? C35 C36 C31 120.30(15) . . ? C42 C41 C46 119.95(14) . . ? C42 C41 N22 119.78(13) . . ? C46 C41 N22 120.25(13) . . ? C41 C42 C43 120.75(14) . . ? C44 C43 C42 118.56(15) . . ? C43 C44 C45 121.59(15) . . ? C43 C44 Cl2 118.62(13) . . ? C45 C44 Cl2 119.79(14) . . ? C44 C45 C46 119.30(16) . . ? C41 C46 C45 119.85(15) . . ? F1 B F2 108.99(12) . . ? F1 B N11 111.87(12) . . ? F2 B N11 109.29(12) . . ? F1 B N22 110.69(12) . . ? F2 B N22 108.07(12) . . ? N11 B N22 107.84(11) . . ? Cl1S C1S Cl2S 113.3(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 N11 C11 C21 -173.62(12) . . . . ? B N11 C11 C21 12.8(2) . . . . ? C14 N11 C11 C12 3.52(15) . . . . ? B N11 C11 C12 -170.09(12) . . . . ? C31 N12 C12 C13 -6.4(3) . . . . ? C31 N12 C12 C11 177.86(12) . . . . ? N11 C11 C12 N12 174.06(12) . . . . ? C21 C11 C12 N12 -9.1(2) . . . . ? N11 C11 C12 C13 -2.96(14) . . . . ? C21 C11 C12 C13 173.88(14) . . . . ? N12 C12 C13 C18 3.3(3) . . . . ? C11 C12 C13 C18 179.43(15) . . . . ? N12 C12 C13 C14 -174.98(16) . . . . ? C11 C12 C13 C14 1.20(14) . . . . ? C18 C13 C14 C15 2.0(2) . . . . ? C12 C13 C14 C15 -179.46(13) . . . . ? C18 C13 C14 N11 -177.70(12) . . . . ? C12 C13 C14 N11 0.83(15) . . . . ? C11 N11 C14 C15 177.58(14) . . . . ? B N11 C14 C15 -9.4(2) . . . . ? C11 N11 C14 C13 -2.73(15) . . . . ? B N11 C14 C13 170.27(13) . . . . ? C13 C14 C15 C16 -1.1(2) . . . . ? N11 C14 C15 C16 178.59(14) . . . . ? C14 C15 C16 C17 -0.3(2) . . . . ? C15 C16 C17 C18 0.8(3) . . . . ? C16 C17 C18 C13 0.2(2) . . . . ? C14 C13 C18 C17 -1.5(2) . . . . ? C12 C13 C18 C17 -179.55(15) . . . . ? N11 C11 C21 N21 177.06(13) . . . . ? C12 C11 C21 N21 0.5(2) . . . . ? N11 C11 C21 C22 4.9(2) . . . . ? C12 C11 C21 C22 -171.69(13) . . . . ? C24 N21 C21 C11 -173.31(13) . . . . ? C24 N21 C21 C22 -0.34(15) . . . . ? C41 N22 C22 C21 172.93(12) . . . . ? B N22 C22 C21 -9.05(19) . . . . ? C41 N22 C22 C23 -7.1(2) . . . . ? B N22 C22 C23 170.93(14) . . . . ? C11 C21 C22 N22 -6.7(2) . . . . ? N21 C21 C22 N22 179.81(12) . . . . ? C11 C21 C22 C23 173.30(12) . . . . ? N21 C21 C22 C23 -0.17(15) . . . . ? N22 C22 C23 C28 -2.7(3) . . . . ? C21 C22 C23 C28 177.26(15) . . . . ? N22 C22 C23 C24 -179.39(14) . . . . ? C21 C22 C23 C24 0.60(14) . . . . ? C21 N21 C24 C25 179.61(13) . . . . ? C21 N21 C24 C23 0.74(15) . . . . ? C28 C23 C24 N21 -178.17(12) . . . . ? C22 C23 C24 N21 -0.83(15) . . . . ? C28 C23 C24 C25 2.9(2) . . . . ? C22 C23 C24 C25 -179.78(12) . . . . ? N21 C24 C25 C26 179.47(13) . . . . ? C23 C24 C25 C26 -1.8(2) . . . . ? C24 C25 C26 C27 -0.6(2) . . . . ? C25 C26 C27 C28 1.9(2) . . . . ? C26 C27 C28 C23 -0.7(2) . . . . ? C24 C23 C28 C27 -1.6(2) . . . . ? C22 C23 C28 C27 -177.91(15) . . . . ? C12 N12 C31 C32 -57.4(2) . . . . ? C12 N12 C31 C36 129.03(15) . . . . ? C36 C31 C32 C33 -1.2(2) . . . . ? N12 C31 C32 C33 -174.63(14) . . . . ? C31 C32 C33 C34 -0.6(2) . . . . ? C32 C33 C34 C35 0.9(3) . . . . ? C32 C33 C34 Cl1 179.84(13) . . . . ? C33 C34 C35 C36 0.6(3) . . . . ? Cl1 C34 C35 C36 -178.37(13) . . . . ? C34 C35 C36 C31 -2.4(3) . . . . ? C32 C31 C36 C35 2.7(2) . . . . ? N12 C31 C36 C35 176.41(15) . . . . ? C22 N22 C41 C42 -62.81(18) . . . . ? B N22 C41 C42 119.08(15) . . . . ? C22 N22 C41 C46 118.82(16) . . . . ? B N22 C41 C46 -59.29(19) . . . . ? C46 C41 C42 C43 -0.7(2) . . . . ? N22 C41 C42 C43 -179.03(13) . . . . ? C41 C42 C43 C44 0.3(2) . . . . ? C42 C43 C44 C45 0.3(3) . . . . ? C42 C43 C44 Cl2 -179.44(13) . . . . ? C43 C44 C45 C46 -0.4(3) . . . . ? Cl2 C44 C45 C46 179.32(16) . . . . ? C42 C41 C46 C45 0.5(3) . . . . ? N22 C41 C46 C45 178.90(16) . . . . ? C44 C45 C46 C41 0.0(3) . . . . ? C11 N11 B F1 -146.66(13) . . . . ? C14 N11 B F1 41.2(2) . . . . ? C11 N11 B F2 92.54(15) . . . . ? C14 N11 B F2 -79.57(17) . . . . ? C11 N11 B N22 -24.71(17) . . . . ? C14 N11 B N22 163.18(12) . . . . ? C22 N22 B F1 145.41(13) . . . . ? C41 N22 B F1 -36.53(17) . . . . ? C22 N22 B F2 -95.30(15) . . . . ? C41 N22 B F2 82.76(15) . . . . ? C22 N22 B N11 22.74(18) . . . . ? C41 N22 B N11 -159.20(11) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 70.07 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.284 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.043