# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Heiden, Zachariah' 'Stephan, Douglas' _publ_contact_author_name 'Stephan, Douglas' _publ_contact_author_email dstephan@chem.utoronto.ca _publ_section_title ; Metal-Free Diastereoselective Catalytic Hydrogenations of Imines Using B(C6F5)3+ ; # Attachment 'zmh031.cif' data_zmh031_4 _database_code_depnum_ccdc_archive 'CCDC 809425' #TrackingRef 'zmh031.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C35 H27 B F15 N' _chemical_formula_sum 'C35 H27 B F15 N' _chemical_formula_weight 757.39 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 Monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 18.0599(8) _cell_length_b 10.8893(5) _cell_length_c 18.3548(8) _cell_angle_alpha 90.00 _cell_angle_beta 115.315(2) _cell_angle_gamma 90.00 _cell_volume 3263.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9875 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 32.12 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.542 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 62851 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0560 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.23 _diffrn_reflns_theta_max 36.41 _reflns_number_total 29412 _reflns_number_gt 16105 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0791P)^2^+0.5712P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(4) _refine_ls_number_reflns 29412 _refine_ls_number_parameters 951 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1273 _refine_ls_R_factor_gt 0.0636 _refine_ls_wR_factor_ref 0.1846 _refine_ls_wR_factor_gt 0.1527 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.108 _refine_ls_shift/su_mean 0.004 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 0.57238(9) 0.78073(16) 0.74816(9) 0.0416(4) Uani 1 1 d . . . F2 F 0.69326(11) 0.69555(17) 0.71652(11) 0.0515(4) Uani 1 1 d . . . F3 F 0.80469(10) 0.85341(19) 0.70380(11) 0.0543(5) Uani 1 1 d . . . F4 F 0.79025(10) 1.09964(19) 0.72496(12) 0.0567(5) Uani 1 1 d . . . F5 F 0.67302(9) 1.18462(16) 0.76019(10) 0.0423(4) Uani 1 1 d . . . F6 F 0.66184(10) 1.13038(17) 0.93229(9) 0.0521(4) Uani 1 1 d . . . F7 F 0.69476(15) 1.0512(2) 1.07968(10) 0.0835(7) Uani 1 1 d . . . F8 F 0.61566(16) 0.8499(2) 1.10085(11) 0.0855(8) Uani 1 1 d . . . F9 F 0.50363(12) 0.7304(2) 0.97003(12) 0.0659(6) Uani 1 1 d . . . F10 F 0.46574(9) 0.81281(16) 0.82187(9) 0.0450(4) Uani 1 1 d . . . F11 F 0.40672(8) 1.12694(15) 0.80158(8) 0.0357(3) Uani 1 1 d . . . F12 F 0.24779(8) 1.09862(15) 0.70476(9) 0.0407(4) Uani 1 1 d . . . F13 F 0.19983(8) 0.96623(16) 0.56566(9) 0.0439(4) Uani 1 1 d . . . F14 F 0.31519(9) 0.87592(17) 0.52179(8) 0.0450(4) Uani 1 1 d . . . F15 F 0.47348(8) 0.91461(16) 0.61286(8) 0.0395(4) Uani 1 1 d . . . F16 F 1.03457(10) 0.23854(17) 0.17188(10) 0.0493(4) Uani 1 1 d . . . F17 F 0.99767(14) 0.3187(2) 0.02396(12) 0.0719(6) Uani 1 1 d . . . F18 F 0.88371(16) 0.1991(3) -0.10676(11) 0.0872(8) Uani 1 1 d . . . F19 F 0.80652(15) -0.0033(2) -0.08450(10) 0.0814(7) Uani 1 1 d . . . F20 F 0.83947(11) -0.08060(18) 0.06340(10) 0.0552(5) Uani 1 1 d . . . F21 F 0.83297(9) -0.13132(15) 0.24486(9) 0.0405(3) Uani 1 1 d . . . F22 F 0.71633(10) -0.04437(17) 0.28162(11) 0.0501(4) Uani 1 1 d . . . F23 F 0.69969(11) 0.20309(18) 0.29693(11) 0.0544(5) Uani 1 1 d . . . F24 F 0.80523(11) 0.36066(15) 0.27471(10) 0.0490(4) Uani 1 1 d . . . F25 F 0.92410(9) 0.27489(15) 0.23773(9) 0.0390(3) Uani 1 1 d . . . F26 F 1.02686(8) 0.15662(16) 0.37717(8) 0.0418(4) Uani 1 1 d . . . F27 F 1.18470(9) 0.19052(17) 0.46933(9) 0.0467(4) Uani 1 1 d . . . F28 F 1.30062(8) 0.08727(18) 0.43066(10) 0.0498(4) Uani 1 1 d . . . F29 F 1.25316(10) -0.05763(19) 0.29733(11) 0.0537(5) Uani 1 1 d . . . F30 F 1.09405(9) -0.08535(16) 0.19929(9) 0.0444(4) Uani 1 1 d . . . N1 N 0.09841(11) 0.1073(2) 0.74408(11) 0.0330(4) Uani 1 1 d . . . H1A H 0.1374 0.1385 0.7294 0.040 Uiso 1 1 calc R . . H1B H 0.0938 0.0245 0.7331 0.040 Uiso 1 1 calc R . . N2 N 0.42421(19) 0.8818(3) 0.24765(15) 0.0695(9) Uani 1 1 d . . . H2A H 0.3805 0.8582 0.2576 0.083 Uiso 1 1 calc R . . H2B H 0.4576 0.8144 0.2565 0.083 Uiso 1 1 calc R . . C1 C 0.01711(12) 0.1689(2) 0.69470(12) 0.0338(5) Uani 1 1 d . . . H1 H 0.0189 0.2540 0.7157 0.041 Uiso 1 1 calc R . . C2 C -0.00700(13) 0.1763(2) 0.60397(13) 0.0332(4) Uani 1 1 d . . . C3 C -0.0727(2) 0.2783(3) 0.5758(2) 0.0674(10) Uani 1 1 d . . . H3A H -0.0538 0.3513 0.6111 0.081 Uiso 1 1 calc R . . H3B H -0.0864 0.3031 0.5196 0.081 Uiso 1 1 calc R . . C4 C -0.1457(2) 0.2193(4) 0.5821(2) 0.0743(12) Uani 1 1 d . . . H4A H -0.1935 0.2162 0.5289 0.089 Uiso 1 1 calc R . . H4B H -0.1612 0.2650 0.6203 0.089 Uiso 1 1 calc R . . C5 C -0.11579(16) 0.0902(4) 0.61337(16) 0.0554(8) Uani 1 1 d . . . H5 H -0.1606 0.0292 0.6029 0.066 Uiso 1 1 calc R . . C6 C -0.05332(15) 0.0988(4) 0.70195(15) 0.0557(9) Uani 1 1 d . . . H6A H -0.0356 0.0164 0.7259 0.067 Uiso 1 1 calc R . . H6B H -0.0757 0.1450 0.7345 0.067 Uiso 1 1 calc R . . C7 C 0.06235(18) 0.1989(4) 0.58044(16) 0.0577(9) Uani 1 1 d . . . H7A H 0.0935 0.2712 0.6091 0.087 Uiso 1 1 calc R . . H7B H 0.0400 0.2131 0.5222 0.087 Uiso 1 1 calc R . . H7C H 0.0985 0.1271 0.5947 0.087 Uiso 1 1 calc R . . C8 C -0.06024(14) 0.0614(2) 0.56962(13) 0.0351(5) Uani 1 1 d . . . C9 C -0.1069(2) 0.0621(4) 0.47699(15) 0.0590(8) Uani 1 1 d . . . H9A H -0.1353 0.1408 0.4592 0.089 Uiso 1 1 calc R . . H9B H -0.1470 -0.0048 0.4597 0.089 Uiso 1 1 calc R . . H9C H -0.0681 0.0509 0.4532 0.089 Uiso 1 1 calc R . . C10 C -0.0139(3) -0.0599(3) 0.5935(2) 0.0811(13) Uani 1 1 d . . . H10A H 0.0337 -0.0570 0.5809 0.122 Uiso 1 1 calc R . . H10B H -0.0501 -0.1272 0.5634 0.122 Uiso 1 1 calc R . . H10C H 0.0046 -0.0735 0.6514 0.122 Uiso 1 1 calc R . . C11 C 0.12650(15) 0.1267(3) 0.83532(14) 0.0400(5) Uani 1 1 d . . . H11A H 0.1432 0.2131 0.8500 0.048 Uiso 1 1 calc R . . H11B H 0.0813 0.1075 0.8503 0.048 Uiso 1 1 calc R . . C12 C 0.19746(15) 0.0425(2) 0.87832(12) 0.0339(5) Uani 1 1 d . . . C13 C 0.18554(18) -0.0700(3) 0.90633(14) 0.0422(6) Uani 1 1 d . . . H13 H 0.1329 -0.0910 0.9024 0.051 Uiso 1 1 calc R . . C14 C 0.2495(2) -0.1522(3) 0.93994(17) 0.0545(8) Uani 1 1 d . . . H14 H 0.2403 -0.2301 0.9579 0.065 Uiso 1 1 calc R . . C15 C 0.3267(2) -0.1214(4) 0.94749(18) 0.0609(9) Uani 1 1 d . . . H15 H 0.3707 -0.1779 0.9708 0.073 Uiso 1 1 calc R . . C16 C 0.33955(18) -0.0083(4) 0.92093(17) 0.0547(8) Uani 1 1 d . . . H16 H 0.3926 0.0130 0.9260 0.066 Uiso 1 1 calc R . . C17 C 0.27510(16) 0.0747(3) 0.88668(14) 0.0423(6) Uani 1 1 d . . . H17 H 0.2842 0.1530 0.8691 0.051 Uiso 1 1 calc R . . C18 C 0.61485(12) 0.9868(2) 0.75470(12) 0.0288(5) Uani 1 1 d . . . C19 C 0.62533(14) 0.8630(2) 0.74381(13) 0.0313(5) Uani 1 1 d . . . C20 C 0.68769(16) 0.8161(3) 0.72718(14) 0.0371(6) Uani 1 1 d . . . C21 C 0.74427(14) 0.8961(3) 0.72080(14) 0.0374(6) Uani 1 1 d . . . C22 C 0.73629(14) 1.0197(3) 0.73069(14) 0.0396(6) Uani 1 1 d . . . C23 C 0.67317(13) 1.0611(3) 0.74842(13) 0.0326(5) Uani 1 1 d . . . C24 C 0.56102(13) 0.9778(2) 0.86928(12) 0.0284(5) Uani 1 1 d . . . C25 C 0.61966(15) 1.0314(3) 0.93862(14) 0.0380(6) Uani 1 1 d . . . C26 C 0.6384(2) 0.9924(3) 1.01528(15) 0.0525(8) Uani 1 1 d . . . C27 C 0.5990(2) 0.8906(4) 1.02651(15) 0.0551(9) Uani 1 1 d . . . C28 C 0.54105(18) 0.8312(3) 0.95966(17) 0.0450(7) Uani 1 1 d . . . C29 C 0.52329(14) 0.8764(3) 0.88343(14) 0.0335(5) Uani 1 1 d . . . C30 C 0.44863(12) 1.0142(2) 0.71546(12) 0.0254(4) Uani 1 1 d . . . C31 C 0.38690(12) 1.0609(2) 0.73308(12) 0.0266(4) Uani 1 1 d . . . C32 C 0.30410(13) 1.0474(2) 0.68433(14) 0.0302(5) Uani 1 1 d . . . C33 C 0.28001(12) 0.9817(2) 0.61358(13) 0.0311(5) Uani 1 1 d . . . C34 C 0.33810(13) 0.9375(3) 0.59121(13) 0.0317(5) Uani 1 1 d . . . C35 C 0.42056(13) 0.9567(2) 0.64169(12) 0.0284(4) Uani 1 1 d . . . C36 C 0.46959(17) 0.9750(3) 0.30635(15) 0.0512(7) Uani 1 1 d . . . H36 H 0.4311 1.0455 0.2969 0.061 Uiso 1 1 calc R . . C37 C 0.49804(15) 0.9372(3) 0.39566(14) 0.0420(6) Uani 1 1 d . . . C38 C 0.4995(2) 1.0588(3) 0.43679(19) 0.0605(8) Uani 1 1 d . . . H38A H 0.5070 1.0465 0.4930 0.073 Uiso 1 1 calc R . . H38B H 0.4486 1.1063 0.4069 0.073 Uiso 1 1 calc R . . C39 C 0.5755(3) 1.1234(3) 0.4338(2) 0.0723(10) Uani 1 1 d . . . H39A H 0.5593 1.2008 0.4025 0.087 Uiso 1 1 calc R . . H39B H 0.6175 1.1420 0.4888 0.087 Uiso 1 1 calc R . . C40 C 0.60741(16) 1.0301(3) 0.39214(17) 0.0498(7) Uani 1 1 d . . . H40 H 0.6658 1.0428 0.4022 0.060 Uiso 1 1 calc R . . C41 C 0.54715(16) 1.0286(3) 0.30272(17) 0.0508(7) Uani 1 1 d . . . H41A H 0.5669 0.9754 0.2710 0.061 Uiso 1 1 calc R . . H41B H 0.5372 1.1124 0.2795 0.061 Uiso 1 1 calc R . . C42 C 0.4477(2) 0.8380(5) 0.4131(2) 0.0802(14) Uani 1 1 d . . . H42A H 0.4634 0.8345 0.4712 0.120 Uiso 1 1 calc R . . H42B H 0.4582 0.7582 0.3946 0.120 Uiso 1 1 calc R . . H42C H 0.3893 0.8577 0.3846 0.120 Uiso 1 1 calc R . . C43 C 0.59104(15) 0.9070(3) 0.42457(15) 0.0415(5) Uani 1 1 d . . . C44 C 0.63746(18) 0.8929(3) 0.51612(17) 0.0553(7) Uani 1 1 d . . . H44A H 0.6170 0.8205 0.5336 0.083 Uiso 1 1 calc R . . H44B H 0.6290 0.9662 0.5426 0.083 Uiso 1 1 calc R . . H44C H 0.6961 0.8829 0.5308 0.083 Uiso 1 1 calc R . . C45 C 0.6101(3) 0.7963(4) 0.3856(2) 0.0806(13) Uani 1 1 d . . . H45A H 0.5821 0.8044 0.3269 0.121 Uiso 1 1 calc R . . H45B H 0.5913 0.7217 0.4023 0.121 Uiso 1 1 calc R . . H45C H 0.6694 0.7913 0.4025 0.121 Uiso 1 1 calc R . . C46 C 0.3921(2) 0.9151(4) 0.16068(17) 0.0729(11) Uani 1 1 d . . . H46A H 0.3754 0.8386 0.1285 0.088 Uiso 1 1 calc R . . H46B H 0.4374 0.9517 0.1512 0.088 Uiso 1 1 calc R . . C47 C 0.3210(2) 1.0026(3) 0.12950(16) 0.0537(8) Uani 1 1 d . . . C48 C 0.3320(2) 1.1195(3) 0.10548(18) 0.0550(8) Uani 1 1 d . . . H48 H 0.3841 1.1427 0.1090 0.066 Uiso 1 1 calc R . . C49 C 0.2685(3) 1.2020(3) 0.0767(2) 0.0675(10) Uani 1 1 d . . . H49 H 0.2768 1.2822 0.0612 0.081 Uiso 1 1 calc R . . C50 C 0.1931(3) 1.1676(4) 0.0706(2) 0.0751(11) Uani 1 1 d . . . H50 H 0.1491 1.2246 0.0507 0.090 Uiso 1 1 calc R . . C51 C 0.1800(3) 1.0504(4) 0.0931(3) 0.0759(11) Uani 1 1 d . . . H51 H 0.1273 1.0276 0.0883 0.091 Uiso 1 1 calc R . . C52 C 0.2434(3) 0.9683(4) 0.12208(19) 0.0647(10) Uani 1 1 d . . . H52 H 0.2348 0.8880 0.1372 0.078 Uiso 1 1 calc R . . C53 C 0.93959(13) 0.0740(2) 0.12594(12) 0.0292(5) Uani 1 1 d . . . C54 C 0.97717(15) 0.1758(3) 0.11089(14) 0.0369(5) Uani 1 1 d . . . C55 C 0.95874(19) 0.2181(3) 0.03332(18) 0.0490(7) Uani 1 1 d . . . C56 C 0.9012(2) 0.1585(4) -0.03223(16) 0.0567(9) Uani 1 1 d . . . C57 C 0.8627(2) 0.0589(3) -0.02114(14) 0.0527(8) Uani 1 1 d . . . C58 C 0.88115(16) 0.0184(3) 0.05709(14) 0.0381(6) Uani 1 1 d . . . C59 C 0.88615(13) 0.0680(2) 0.23998(12) 0.0261(4) Uani 1 1 d . . . C60 C 0.82981(13) -0.0073(2) 0.25171(13) 0.0280(4) Uani 1 1 d . . . C61 C 0.76741(14) 0.0357(3) 0.27016(13) 0.0329(5) Uani 1 1 d . . . C62 C 0.75871(15) 0.1598(3) 0.27772(14) 0.0368(6) Uani 1 1 d . . . C63 C 0.81231(16) 0.2386(2) 0.26628(14) 0.0339(5) Uani 1 1 d . . . C64 C 0.87285(15) 0.1916(2) 0.24759(13) 0.0311(5) Uani 1 1 d . . . C65 C 1.05109(13) 0.0385(2) 0.28004(12) 0.0259(4) Uani 1 1 d . . . C66 C 1.07997(14) 0.1054(2) 0.35185(13) 0.0293(5) Uani 1 1 d . . . C67 C 1.16207(15) 0.1219(3) 0.40186(14) 0.0330(5) Uani 1 1 d . . . C68 C 1.22086(13) 0.0682(3) 0.38311(15) 0.0357(5) Uani 1 1 d . . . C69 C 1.19599(15) -0.0014(3) 0.31478(15) 0.0354(5) Uani 1 1 d . . . C70 C 1.11331(14) -0.0148(2) 0.26493(13) 0.0310(5) Uani 1 1 d . . . B1 B 0.54357(14) 1.0365(3) 0.78077(14) 0.0262(5) Uani 1 1 d . . . B2 B 0.95645(15) 0.0165(3) 0.21433(14) 0.0270(5) Uani 1 1 d . . . H100 H 0.5454(16) 1.136(3) 0.7869(16) 0.033(7) Uiso 1 1 d . . . H101 H 0.9454(13) -0.091(2) 0.2050(13) 0.015(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0435(8) 0.0392(9) 0.0476(8) -0.0108(7) 0.0248(7) -0.0112(7) F2 0.0546(9) 0.0496(11) 0.0600(10) -0.0110(8) 0.0336(9) 0.0066(8) F3 0.0366(8) 0.0802(14) 0.0573(10) -0.0086(9) 0.0307(8) 0.0070(8) F4 0.0387(8) 0.0738(14) 0.0732(11) -0.0102(10) 0.0387(8) -0.0180(8) F5 0.0345(7) 0.0432(10) 0.0553(9) -0.0028(7) 0.0250(7) -0.0077(6) F6 0.0486(8) 0.0525(11) 0.0368(8) -0.0125(7) 0.0007(7) -0.0166(8) F7 0.1034(16) 0.0846(16) 0.0274(8) -0.0127(9) -0.0056(10) 0.0089(14) F8 0.131(2) 0.0876(17) 0.0386(9) 0.0269(10) 0.0375(12) 0.0445(15) F9 0.0719(12) 0.0676(13) 0.0753(12) 0.0349(10) 0.0476(11) 0.0155(10) F10 0.0360(7) 0.0471(10) 0.0491(8) 0.0056(7) 0.0155(7) -0.0125(7) F11 0.0308(6) 0.0461(9) 0.0312(6) -0.0084(6) 0.0142(5) 0.0004(6) F12 0.0250(6) 0.0523(10) 0.0476(8) -0.0014(7) 0.0181(6) 0.0031(6) F13 0.0216(6) 0.0505(10) 0.0477(8) -0.0019(7) 0.0034(6) -0.0052(6) F14 0.0394(7) 0.0530(10) 0.0313(6) -0.0135(7) 0.0044(6) -0.0061(7) F15 0.0332(7) 0.0560(10) 0.0314(6) -0.0133(6) 0.0160(6) -0.0033(6) F16 0.0499(9) 0.0460(10) 0.0465(9) 0.0068(7) 0.0153(7) -0.0148(8) F17 0.0866(14) 0.0615(13) 0.0768(13) 0.0358(11) 0.0436(12) 0.0029(11) F18 0.1249(19) 0.1003(19) 0.0363(9) 0.0299(10) 0.0344(11) 0.0205(16) F19 0.0943(15) 0.0942(17) 0.0255(8) -0.0082(9) -0.0032(9) -0.0029(14) F20 0.0549(10) 0.0571(12) 0.0407(8) -0.0097(8) 0.0080(8) -0.0173(9) F21 0.0414(8) 0.0321(8) 0.0553(9) -0.0036(7) 0.0276(7) -0.0056(6) F22 0.0421(8) 0.0556(11) 0.0660(10) -0.0009(9) 0.0359(8) -0.0055(8) F23 0.0499(9) 0.0647(13) 0.0626(11) 0.0034(9) 0.0376(9) 0.0175(9) F24 0.0666(10) 0.0331(9) 0.0584(9) -0.0004(7) 0.0374(9) 0.0121(8) F25 0.0476(8) 0.0321(8) 0.0456(8) -0.0001(6) 0.0279(7) -0.0032(6) F26 0.0358(7) 0.0568(10) 0.0343(7) -0.0159(7) 0.0165(6) 0.0001(7) F27 0.0431(8) 0.0527(10) 0.0364(7) -0.0144(7) 0.0094(7) -0.0085(7) F28 0.0268(6) 0.0636(12) 0.0491(9) 0.0056(8) 0.0069(6) -0.0074(7) F29 0.0400(8) 0.0644(12) 0.0618(11) -0.0014(9) 0.0265(8) 0.0156(8) F30 0.0444(8) 0.0514(10) 0.0405(7) -0.0128(7) 0.0211(7) 0.0071(7) N1 0.0265(7) 0.0463(12) 0.0273(8) 0.0050(8) 0.0126(6) 0.0076(8) N2 0.0732(18) 0.072(2) 0.0428(13) 0.0132(13) 0.0057(13) -0.0233(15) C1 0.0276(9) 0.0443(13) 0.0272(9) -0.0023(9) 0.0094(8) 0.0045(9) C2 0.0313(9) 0.0352(12) 0.0303(9) 0.0018(9) 0.0106(8) -0.0025(9) C3 0.085(2) 0.0473(18) 0.0544(17) 0.0038(14) 0.0147(16) 0.0348(17) C4 0.0475(16) 0.106(3) 0.067(2) -0.007(2) 0.0223(16) 0.0316(19) C5 0.0321(11) 0.091(3) 0.0420(13) -0.0064(15) 0.0151(10) -0.0207(14) C6 0.0320(11) 0.104(3) 0.0340(11) -0.0093(14) 0.0172(10) -0.0200(14) C7 0.0480(15) 0.094(3) 0.0324(12) 0.0072(14) 0.0179(12) -0.0131(16) C8 0.0437(11) 0.0280(11) 0.0294(9) -0.0019(8) 0.0116(9) -0.0013(9) C9 0.0625(17) 0.073(2) 0.0303(11) -0.0038(13) 0.0087(12) -0.0111(16) C10 0.137(4) 0.0350(17) 0.0547(19) -0.0034(14) 0.026(2) 0.012(2) C11 0.0394(11) 0.0469(15) 0.0280(10) 0.0055(10) 0.0091(9) 0.0007(11) C12 0.0401(11) 0.0386(14) 0.0201(8) 0.0005(8) 0.0101(8) -0.0006(10) C13 0.0523(14) 0.0491(17) 0.0265(10) 0.0015(10) 0.0179(10) -0.0024(12) C14 0.077(2) 0.0466(18) 0.0424(14) 0.0134(12) 0.0284(14) 0.0122(15) C15 0.0659(19) 0.075(2) 0.0469(15) 0.0212(16) 0.0289(15) 0.0323(18) C16 0.0424(13) 0.085(3) 0.0404(13) -0.0004(14) 0.0215(12) 0.0101(14) C17 0.0465(13) 0.0514(17) 0.0297(10) 0.0011(11) 0.0171(10) -0.0052(12) C18 0.0197(8) 0.0443(14) 0.0235(9) -0.0048(9) 0.0103(7) -0.0038(8) C19 0.0273(10) 0.0426(15) 0.0264(9) -0.0064(9) 0.0138(8) -0.0068(9) C20 0.0379(12) 0.0447(16) 0.0297(10) -0.0087(10) 0.0156(10) 0.0048(11) C21 0.0270(10) 0.0598(19) 0.0284(10) -0.0034(11) 0.0148(9) 0.0028(11) C22 0.0258(10) 0.064(2) 0.0316(11) -0.0060(11) 0.0147(9) -0.0109(11) C23 0.0244(9) 0.0468(16) 0.0258(9) -0.0040(9) 0.0099(8) -0.0051(10) C24 0.0263(9) 0.0360(13) 0.0241(9) -0.0029(8) 0.0120(8) 0.0022(9) C25 0.0359(11) 0.0448(16) 0.0269(10) -0.0045(10) 0.0074(9) 0.0023(11) C26 0.0627(18) 0.055(2) 0.0268(11) -0.0043(11) 0.0071(12) 0.0141(15) C27 0.0684(19) 0.068(2) 0.0295(11) 0.0165(13) 0.0211(13) 0.0325(18) C28 0.0517(15) 0.0486(18) 0.0458(14) 0.0155(12) 0.0317(13) 0.0171(13) C29 0.0318(10) 0.0388(14) 0.0329(10) 0.0035(10) 0.0167(9) 0.0050(10) C30 0.0209(8) 0.0313(12) 0.0239(8) -0.0006(8) 0.0095(7) -0.0028(8) C31 0.0231(8) 0.0328(12) 0.0255(9) -0.0005(8) 0.0120(7) -0.0034(8) C32 0.0216(8) 0.0348(13) 0.0337(10) 0.0010(9) 0.0115(8) -0.0030(9) C33 0.0230(9) 0.0332(13) 0.0302(10) 0.0016(9) 0.0048(8) -0.0074(9) C34 0.0270(9) 0.0372(14) 0.0236(9) -0.0045(8) 0.0038(8) -0.0052(9) C35 0.0240(9) 0.0354(13) 0.0261(9) -0.0019(8) 0.0108(7) -0.0052(8) C36 0.0440(13) 0.071(2) 0.0358(12) 0.0052(12) 0.0139(11) -0.0121(13) C37 0.0408(12) 0.0544(17) 0.0315(10) 0.0029(11) 0.0161(9) -0.0018(11) C38 0.079(2) 0.0552(19) 0.0486(15) 0.0053(14) 0.0278(15) 0.0214(16) C39 0.093(3) 0.0388(17) 0.076(2) -0.0006(16) 0.028(2) 0.0062(17) C40 0.0339(11) 0.063(2) 0.0494(14) 0.0066(13) 0.0150(11) -0.0003(12) C41 0.0427(13) 0.067(2) 0.0485(14) 0.0168(14) 0.0250(12) 0.0014(13) C42 0.074(2) 0.110(3) 0.0449(16) 0.0138(18) 0.0140(16) -0.046(2) C43 0.0430(12) 0.0394(14) 0.0389(12) -0.0023(10) 0.0144(10) 0.0082(10) C44 0.0540(15) 0.0539(18) 0.0442(14) 0.0062(13) 0.0077(12) 0.0117(13) C45 0.110(3) 0.073(3) 0.0562(19) 0.0005(18) 0.034(2) 0.044(2) C46 0.091(2) 0.066(2) 0.0329(13) 0.0161(14) -0.0014(15) -0.019(2) C47 0.096(2) 0.0360(16) 0.0312(12) -0.0053(10) 0.0294(14) -0.0182(15) C48 0.088(2) 0.0412(17) 0.0479(15) -0.0010(13) 0.0406(16) -0.0130(16) C49 0.108(3) 0.0407(19) 0.083(2) 0.0074(17) 0.068(2) 0.0043(19) C50 0.112(3) 0.059(2) 0.078(2) 0.0074(19) 0.063(2) 0.024(2) C51 0.103(3) 0.073(3) 0.078(2) 0.002(2) 0.065(2) -0.010(2) C52 0.103(3) 0.049(2) 0.0434(15) -0.0033(14) 0.0328(18) -0.018(2) C53 0.0301(10) 0.0336(13) 0.0251(9) 0.0017(8) 0.0129(8) 0.0032(9) C54 0.0354(11) 0.0428(15) 0.0347(11) 0.0067(11) 0.0171(10) 0.0035(11) C55 0.0577(17) 0.0476(19) 0.0499(15) 0.0236(13) 0.0307(14) 0.0116(14) C56 0.075(2) 0.067(2) 0.0279(12) 0.0145(13) 0.0217(13) 0.0230(18) C57 0.0636(18) 0.063(2) 0.0218(10) 0.0017(12) 0.0089(11) 0.0147(16) C58 0.0417(13) 0.0413(16) 0.0260(10) 0.0003(10) 0.0095(9) 0.0073(11) C59 0.0282(9) 0.0281(11) 0.0210(8) 0.0011(7) 0.0097(7) -0.0003(8) C60 0.0279(10) 0.0286(12) 0.0271(9) 0.0007(8) 0.0113(8) 0.0010(9) C61 0.0276(10) 0.0419(15) 0.0311(10) 0.0014(10) 0.0142(9) -0.0005(10) C62 0.0341(11) 0.0476(16) 0.0318(11) -0.0014(10) 0.0172(9) 0.0109(11) C63 0.0392(12) 0.0338(14) 0.0308(10) 0.0027(9) 0.0170(10) 0.0049(10) C64 0.0350(11) 0.0305(13) 0.0279(9) 0.0021(9) 0.0137(9) 0.0027(9) C65 0.0299(10) 0.0233(11) 0.0256(9) 0.0016(8) 0.0131(8) -0.0009(8) C66 0.0317(10) 0.0300(13) 0.0275(9) 0.0004(8) 0.0138(8) 0.0025(9) C67 0.0373(11) 0.0305(12) 0.0302(10) 0.0003(9) 0.0135(9) -0.0068(10) C68 0.0265(10) 0.0396(15) 0.0384(11) 0.0090(10) 0.0113(9) 0.0008(10) C69 0.0319(11) 0.0374(14) 0.0413(12) 0.0075(10) 0.0199(10) 0.0099(10) C70 0.0345(11) 0.0292(13) 0.0301(10) 0.0004(9) 0.0144(9) 0.0038(9) B1 0.0217(9) 0.0338(14) 0.0253(9) -0.0050(9) 0.0122(8) -0.0071(9) B2 0.0298(11) 0.0285(14) 0.0243(9) -0.0006(9) 0.0133(9) 0.0008(10) _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 C19 1.338(3) . ? F2 C20 1.338(3) . ? F3 C21 1.340(3) . ? F4 C22 1.344(3) . ? F5 C23 1.362(3) . ? F6 C25 1.353(3) . ? F7 C26 1.346(4) . ? F8 C27 1.341(3) . ? F9 C28 1.345(4) . ? F10 C29 1.354(3) . ? F11 C31 1.357(2) . ? F12 C32 1.346(3) . ? F13 C33 1.345(2) . ? F14 C34 1.339(3) . ? F15 C35 1.355(3) . ? F16 C54 1.342(3) . ? F17 C55 1.352(4) . ? F18 C56 1.341(3) . ? F19 C57 1.353(4) . ? F20 C58 1.348(3) . ? F21 C60 1.360(3) . ? F22 C61 1.349(3) . ? F23 C62 1.343(3) . ? F24 C63 1.350(3) . ? F25 C64 1.362(3) . ? F26 C66 1.352(3) . ? F27 C67 1.351(3) . ? F28 C68 1.343(3) . ? F29 C69 1.351(3) . ? F30 C70 1.343(3) . ? N1 C1 1.513(3) . ? N1 C11 1.543(3) . ? N1 H1A 0.9200 . ? N1 H1B 0.9200 . ? N2 C36 1.452(4) . ? N2 C46 1.491(4) . ? N2 H2A 0.9200 . ? N2 H2B 0.9200 . ? C1 C2 1.533(3) . ? C1 C6 1.537(4) . ? C1 H1 1.0000 . ? C2 C7 1.509(4) . ? C2 C8 1.540(3) . ? C2 C3 1.544(4) . ? C3 C4 1.515(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.528(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.535(4) . ? C5 C8 1.562(4) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C10 1.524(4) . ? C8 C9 1.541(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.497(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.380(4) . ? C12 C17 1.389(4) . ? C13 C14 1.380(4) . ? C13 H13 0.9500 . ? C14 C15 1.383(5) . ? C14 H14 0.9500 . ? C15 C16 1.380(6) . ? C15 H15 0.9500 . ? C16 C17 1.393(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C23 1.372(3) . ? C18 C19 1.387(4) . ? C18 B1 1.645(3) . ? C19 C20 1.384(3) . ? C20 C21 1.385(4) . ? C21 C22 1.374(5) . ? C22 C23 1.388(3) . ? C24 C29 1.379(4) . ? C24 C25 1.389(3) . ? C24 B1 1.646(3) . ? C25 C26 1.366(4) . ? C26 C27 1.379(5) . ? C27 C28 1.387(5) . ? C28 C29 1.385(3) . ? C30 C35 1.377(3) . ? C30 C31 1.384(3) . ? C30 B1 1.636(3) . ? C31 C32 1.384(3) . ? C32 C33 1.380(3) . ? C33 C34 1.367(3) . ? C34 C35 1.393(3) . ? C36 C41 1.545(4) . ? C36 C37 1.549(3) . ? C36 H36 1.0000 . ? C37 C38 1.519(5) . ? C37 C42 1.531(5) . ? C37 C43 1.565(4) . ? C38 C39 1.565(5) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 C40 1.526(5) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 C41 1.533(4) . ? C40 C43 1.545(4) . ? C40 H40 1.0000 . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C43 C45 1.514(4) . ? C43 C44 1.532(4) . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 C47 1.503(5) . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? C47 C48 1.389(4) . ? C47 C52 1.399(5) . ? C48 C49 1.371(5) . ? C48 H48 0.9500 . ? C49 C50 1.370(6) . ? C49 H49 0.9500 . ? C50 C51 1.392(6) . ? C50 H50 0.9500 . ? C51 C52 1.369(6) . ? C51 H51 0.9500 . ? C52 H52 0.9500 . ? C53 C54 1.388(4) . ? C53 C58 1.392(3) . ? C53 B2 1.641(3) . ? C54 C55 1.395(4) . ? C55 C56 1.371(5) . ? C56 C57 1.350(5) . ? C57 C58 1.399(4) . ? C59 C64 1.385(4) . ? C59 C60 1.394(3) . ? C59 B2 1.631(3) . ? C60 C61 1.389(3) . ? C61 C62 1.375(4) . ? C62 C63 1.375(4) . ? C63 C64 1.377(3) . ? C65 C70 1.394(3) . ? C65 C66 1.397(3) . ? C65 B2 1.634(3) . ? C66 C67 1.382(3) . ? C67 C68 1.379(4) . ? C68 C69 1.367(4) . ? C69 C70 1.386(3) . ? B1 H100 1.09(3) . ? B2 H101 1.18(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 C1 N1 C11 111.95(17) . . ? C1 N1 H1A 109.2 . . ? C11 N1 H1A 109.2 . . ? C1 N1 H1B 109.2 . . ? C11 N1 H1B 109.2 . . ? H1A N1 H1B 107.9 . . ? C36 N2 C46 117.5(3) . . ? C36 N2 H2A 107.9 . . ? C46 N2 H2A 107.9 . . ? C36 N2 H2B 107.9 . . ? C46 N2 H2B 107.9 . . ? H2A N2 H2B 107.2 . . ? N1 C1 C2 115.24(18) . . ? N1 C1 C6 110.8(2) . . ? C2 C1 C6 105.02(18) . . ? N1 C1 H1 108.5 . . ? C2 C1 H1 108.5 . . ? C6 C1 H1 108.5 . . ? C7 C2 C1 115.75(19) . . ? C7 C2 C8 117.7(2) . . ? C1 C2 C8 103.85(19) . . ? C7 C2 C3 113.6(3) . . ? C1 C2 C3 102.8(2) . . ? C8 C2 C3 101.0(2) . . ? C4 C3 C2 103.9(3) . . ? C4 C3 H3A 111.0 . . ? C2 C3 H3A 111.0 . . ? C4 C3 H3B 111.0 . . ? C2 C3 H3B 111.0 . . ? H3A C3 H3B 109.0 . . ? C3 C4 C5 103.8(2) . . ? C3 C4 H4A 111.0 . . ? C5 C4 H4A 111.0 . . ? C3 C4 H4B 111.0 . . ? C5 C4 H4B 111.0 . . ? H4A C4 H4B 109.0 . . ? C4 C5 C6 108.9(3) . . ? C4 C5 C8 101.2(2) . . ? C6 C5 C8 102.4(2) . . ? C4 C5 H5 114.3 . . ? C6 C5 H5 114.3 . . ? C8 C5 H5 114.3 . . ? C5 C6 C1 101.5(2) . . ? C5 C6 H6A 111.5 . . ? C1 C6 H6A 111.5 . . ? C5 C6 H6B 111.5 . . ? C1 C6 H6B 111.5 . . ? H6A C6 H6B 109.3 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C10 C8 C2 114.6(2) . . ? C10 C8 C9 107.2(2) . . ? C2 C8 C9 113.5(2) . . ? C10 C8 C5 114.9(3) . . ? C2 C8 C5 92.98(19) . . ? C9 C8 C5 113.4(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 N1 107.4(2) . . ? C12 C11 H11A 110.2 . . ? N1 C11 H11A 110.2 . . ? C12 C11 H11B 110.2 . . ? N1 C11 H11B 110.2 . . ? H11A C11 H11B 108.5 . . ? C13 C12 C17 119.6(3) . . ? C13 C12 C11 120.4(2) . . ? C17 C12 C11 120.0(3) . . ? C14 C13 C12 120.5(3) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 120.2(3) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C16 C15 C14 119.7(3) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 120.3(3) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C12 C17 C16 119.7(3) . . ? C12 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C23 C18 C19 113.8(2) . . ? C23 C18 B1 123.7(2) . . ? C19 C18 B1 122.3(2) . . ? F1 C19 C20 115.8(2) . . ? F1 C19 C18 119.8(2) . . ? C20 C19 C18 124.4(2) . . ? F2 C20 C19 120.9(3) . . ? F2 C20 C21 120.0(2) . . ? C19 C20 C21 119.0(3) . . ? F3 C21 C22 120.9(3) . . ? F3 C21 C20 120.3(3) . . ? C22 C21 C20 118.8(2) . . ? F4 C22 C21 120.2(2) . . ? F4 C22 C23 120.3(3) . . ? C21 C22 C23 119.5(3) . . ? F5 C23 C18 121.0(2) . . ? F5 C23 C22 114.5(2) . . ? C18 C23 C22 124.4(3) . . ? C29 C24 C25 114.1(2) . . ? C29 C24 B1 126.53(19) . . ? C25 C24 B1 119.4(2) . . ? F6 C25 C26 115.8(2) . . ? F6 C25 C24 119.5(2) . . ? C26 C25 C24 124.7(3) . . ? F7 C26 C25 121.2(3) . . ? F7 C26 C27 119.7(3) . . ? C25 C26 C27 119.1(3) . . ? F8 C27 C26 120.8(3) . . ? F8 C27 C28 120.1(4) . . ? C26 C27 C28 119.1(2) . . ? F9 C28 C29 121.3(3) . . ? F9 C28 C27 119.4(3) . . ? C29 C28 C27 119.3(3) . . ? F10 C29 C24 121.2(2) . . ? F10 C29 C28 115.1(3) . . ? C24 C29 C28 123.7(2) . . ? C35 C30 C31 113.73(18) . . ? C35 C30 B1 128.15(19) . . ? C31 C30 B1 118.09(18) . . ? F11 C31 C32 116.1(2) . . ? F11 C31 C30 119.45(17) . . ? C32 C31 C30 124.5(2) . . ? F12 C32 C33 120.35(19) . . ? F12 C32 C31 120.8(2) . . ? C33 C32 C31 118.8(2) . . ? F13 C33 C34 120.6(2) . . ? F13 C33 C32 119.9(2) . . ? C34 C33 C32 119.45(19) . . ? F14 C34 C33 119.83(18) . . ? F14 C34 C35 121.0(2) . . ? C33 C34 C35 119.1(2) . . ? F15 C35 C30 120.89(18) . . ? F15 C35 C34 114.93(19) . . ? C30 C35 C34 124.2(2) . . ? N2 C36 C41 117.8(3) . . ? N2 C36 C37 115.2(3) . . ? C41 C36 C37 104.4(2) . . ? N2 C36 H36 106.2 . . ? C41 C36 H36 106.2 . . ? C37 C36 H36 106.2 . . ? C38 C37 C42 113.4(3) . . ? C38 C37 C36 102.8(2) . . ? C42 C37 C36 116.8(2) . . ? C38 C37 C43 103.1(2) . . ? C42 C37 C43 115.3(3) . . ? C36 C37 C43 103.7(2) . . ? C37 C38 C39 101.7(3) . . ? C37 C38 H38A 111.4 . . ? C39 C38 H38A 111.4 . . ? C37 C38 H38B 111.4 . . ? C39 C38 H38B 111.4 . . ? H38A C38 H38B 109.3 . . ? C40 C39 C38 104.1(3) . . ? C40 C39 H39A 110.9 . . ? C38 C39 H39A 110.9 . . ? C40 C39 H39B 110.9 . . ? C38 C39 H39B 110.9 . . ? H39A C39 H39B 109.0 . . ? C39 C40 C41 107.2(3) . . ? C39 C40 C43 102.1(2) . . ? C41 C40 C43 103.8(2) . . ? C39 C40 H40 114.2 . . ? C41 C40 H40 114.2 . . ? C43 C40 H40 114.2 . . ? C40 C41 C36 101.5(2) . . ? C40 C41 H41A 111.5 . . ? C36 C41 H41A 111.5 . . ? C40 C41 H41B 111.5 . . ? C36 C41 H41B 111.5 . . ? H41A C41 H41B 109.3 . . ? C37 C42 H42A 109.5 . . ? C37 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C37 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C45 C43 C44 108.0(2) . . ? C45 C43 C40 112.9(3) . . ? C44 C43 C40 113.9(2) . . ? C45 C43 C37 115.8(3) . . ? C44 C43 C37 113.4(2) . . ? C40 C43 C37 92.4(2) . . ? C43 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C43 C45 H45A 109.5 . . ? C43 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C43 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? N2 C46 C47 116.1(3) . . ? N2 C46 H46A 108.3 . . ? C47 C46 H46A 108.3 . . ? N2 C46 H46B 108.3 . . ? C47 C46 H46B 108.3 . . ? H46A C46 H46B 107.4 . . ? C48 C47 C52 119.1(4) . . ? C48 C47 C46 119.2(3) . . ? C52 C47 C46 121.7(3) . . ? C49 C48 C47 120.9(4) . . ? C49 C48 H48 119.6 . . ? C47 C48 H48 119.6 . . ? C50 C49 C48 119.4(3) . . ? C50 C49 H49 120.3 . . ? C48 C49 H49 120.3 . . ? C49 C50 C51 121.0(4) . . ? C49 C50 H50 119.5 . . ? C51 C50 H50 119.5 . . ? C52 C51 C50 119.6(4) . . ? C52 C51 H51 120.2 . . ? C50 C51 H51 120.2 . . ? C51 C52 C47 120.0(3) . . ? C51 C52 H52 120.0 . . ? C47 C52 H52 120.0 . . ? C54 C53 C58 114.4(2) . . ? C54 C53 B2 127.0(2) . . ? C58 C53 B2 118.7(2) . . ? F16 C54 C53 120.6(2) . . ? F16 C54 C55 116.5(3) . . ? C53 C54 C55 122.9(3) . . ? F17 C55 C56 120.8(3) . . ? F17 C55 C54 119.2(3) . . ? C56 C55 C54 120.0(3) . . ? F18 C56 C57 120.5(3) . . ? F18 C56 C55 119.9(3) . . ? C57 C56 C55 119.6(2) . . ? C56 C57 F19 121.2(3) . . ? C56 C57 C58 119.7(3) . . ? F19 C57 C58 119.1(3) . . ? F20 C58 C53 120.3(2) . . ? F20 C58 C57 116.3(2) . . ? C53 C58 C57 123.4(3) . . ? C64 C59 C60 112.8(2) . . ? C64 C59 B2 123.6(2) . . ? C60 C59 B2 123.5(2) . . ? F21 C60 C61 115.3(2) . . ? F21 C60 C59 120.5(2) . . ? C61 C60 C59 124.2(2) . . ? F22 C61 C62 120.3(2) . . ? F22 C61 C60 120.0(2) . . ? C62 C61 C60 119.7(2) . . ? F23 C62 C61 120.6(3) . . ? F23 C62 C63 120.7(3) . . ? C61 C62 C63 118.7(2) . . ? F24 C63 C62 119.3(2) . . ? F24 C63 C64 121.2(2) . . ? C62 C63 C64 119.4(2) . . ? F25 C64 C63 116.3(2) . . ? F25 C64 C59 118.5(2) . . ? C63 C64 C59 125.2(2) . . ? C70 C65 C66 113.41(19) . . ? C70 C65 B2 118.03(19) . . ? C66 C65 B2 128.6(2) . . ? F26 C66 C67 115.8(2) . . ? F26 C66 C65 120.38(19) . . ? C67 C66 C65 123.8(2) . . ? F27 C67 C68 120.0(2) . . ? F27 C67 C66 119.9(2) . . ? C68 C67 C66 120.1(2) . . ? F28 C68 C69 121.5(2) . . ? F28 C68 C67 119.9(2) . . ? C69 C68 C67 118.6(2) . . ? F29 C69 C68 119.0(2) . . ? F29 C69 C70 120.9(2) . . ? C68 C69 C70 120.2(2) . . ? F30 C70 C69 116.4(2) . . ? F30 C70 C65 119.7(2) . . ? C69 C70 C65 123.9(2) . . ? C30 B1 C18 116.31(17) . . ? C30 B1 C24 111.34(17) . . ? C18 B1 C24 108.42(19) . . ? C30 B1 H100 101.5(14) . . ? C18 B1 H100 111.4(14) . . ? C24 B1 H100 107.5(14) . . ? C59 B2 C65 115.74(18) . . ? C59 B2 C53 108.41(18) . . ? C65 B2 C53 111.54(18) . . ? C59 B2 H101 106.1(11) . . ? C65 B2 H101 108.0(10) . . ? C53 B2 H101 106.5(11) . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 36.41 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 1.052 _refine_diff_density_min -0.476 _refine_diff_density_rms 0.061 _chemical_absolute_configuration rm # Attachment 'zmh032.cif' data_zmh032_19 _database_code_depnum_ccdc_archive 'CCDC 809426' #TrackingRef 'zmh032.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H21 B F15 N' _chemical_formula_sum 'C32 H21 B F15 N' _chemical_formula_weight 715.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' _symmetry_space_group_name_Hall 'P 2ac 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 12.2171(7) _cell_length_b 13.3261(8) _cell_length_c 18.5076(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3013.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7654 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 21.86 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_max 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.577 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 49898 _diffrn_reflns_av_R_equivalents 0.0655 _diffrn_reflns_av_sigmaI/netI 0.0578 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6910 _reflns_number_gt 4939 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0368P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.3(4) _refine_ls_number_reflns 6910 _refine_ls_number_parameters 450 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0724 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0784 _refine_ls_wR_factor_gt 0.0680 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 0.68267(10) 0.28948(9) -0.02492(7) 0.0306(3) Uani 1 1 d . . . F2 F 0.58706(11) 0.45325(10) -0.07234(7) 0.0346(3) Uani 1 1 d . . . F3 F 0.60475(10) 0.63045(9) 0.00117(7) 0.0369(3) Uani 1 1 d . . . F4 F 0.72632(10) 0.63685(9) 0.12434(7) 0.0316(3) Uani 1 1 d . . . F5 F 0.82748(9) 0.47374(9) 0.17235(6) 0.0233(3) Uani 1 1 d . . . F6 F 0.95495(9) 0.12133(9) 0.18240(6) 0.0250(3) Uani 1 1 d . . . F7 F 1.15693(10) 0.13604(10) 0.23180(7) 0.0375(3) Uani 1 1 d . . . F8 F 1.27542(10) 0.30786(11) 0.21225(8) 0.0431(4) Uani 1 1 d . . . F9 F 1.18374(10) 0.46389(10) 0.13840(7) 0.0344(3) Uani 1 1 d . . . F10 F 0.98707(10) 0.44811(9) 0.08199(7) 0.0255(3) Uani 1 1 d . . . F11 F 0.93931(10) 0.29864(9) -0.02601(7) 0.0303(3) Uani 1 1 d . . . F12 F 0.98762(11) 0.16334(10) -0.12714(7) 0.0372(4) Uani 1 1 d . . . F13 F 0.91661(12) -0.02874(11) -0.11428(8) 0.0441(4) Uani 1 1 d . . . F14 F 0.79250(12) -0.08240(10) 0.00261(8) 0.0458(4) Uani 1 1 d . . . F15 F 0.74221(11) 0.04976(9) 0.10346(7) 0.0342(3) Uani 1 1 d . . . N1 N 0.66468(14) 0.35664(14) 0.25492(10) 0.0218(4) Uani 1 1 d . . . C1 C 0.74770(17) 0.29745(15) 0.24254(11) 0.0196(5) Uani 1 1 d . . . C2 C 0.74678(17) 0.23288(15) 0.17793(11) 0.0206(5) Uani 1 1 d . . . H2A H 0.6704 0.2275 0.1605 0.025 Uiso 1 1 calc R . . H2B H 0.7706 0.1648 0.1924 0.025 Uiso 1 1 calc R . . C3 C 0.84302(16) 0.29311(16) 0.29248(11) 0.0203(5) Uani 1 1 d . . . C4 C 0.86935(19) 0.20074(17) 0.32305(12) 0.0270(5) Uani 1 1 d . . . H4 H 0.8234 0.1444 0.3150 0.032 Uiso 1 1 calc R . . C5 C 0.9625(2) 0.19076(18) 0.36531(13) 0.0331(6) Uani 1 1 d . . . H5 H 0.9792 0.1281 0.3871 0.040 Uiso 1 1 calc R . . C6 C 1.0307(2) 0.27153(18) 0.37567(12) 0.0322(6) Uani 1 1 d . . . H6 H 1.0958 0.2637 0.4032 0.039 Uiso 1 1 calc R . . C7 C 1.00533(17) 0.36358(18) 0.34644(12) 0.0260(5) Uani 1 1 d . . . H7 H 1.0526 0.4191 0.3542 0.031 Uiso 1 1 calc R . . C8 C 0.91016(16) 0.37558(17) 0.30543(11) 0.0218(5) Uani 1 1 d . . . H8 H 0.8914 0.4396 0.2865 0.026 Uiso 1 1 calc R . . C9 C 0.64159(17) 0.42443(15) 0.31671(12) 0.0239(5) Uani 1 1 d . . . H9 H 0.7115 0.4352 0.3437 0.029 Uiso 1 1 calc R . . C10 C 0.60594(19) 0.52505(17) 0.28493(14) 0.0344(6) Uani 1 1 d . . . H10A H 0.5382 0.5160 0.2573 0.052 Uiso 1 1 calc R . . H10B H 0.6635 0.5506 0.2529 0.052 Uiso 1 1 calc R . . H10C H 0.5933 0.5731 0.3241 0.052 Uiso 1 1 calc R . . C11 C 0.55831(17) 0.37544(18) 0.36908(12) 0.0283(5) Uani 1 1 d . . . C12 C 0.45044(19) 0.3501(2) 0.33148(14) 0.0447(7) Uani 1 1 d . . . H12A H 0.4225 0.4098 0.3068 0.067 Uiso 1 1 calc R . . H12B H 0.3969 0.3276 0.3675 0.067 Uiso 1 1 calc R . . H12C H 0.4627 0.2965 0.2961 0.067 Uiso 1 1 calc R . . C13 C 0.5363(2) 0.4486(2) 0.43142(14) 0.0399(7) Uani 1 1 d . . . H13A H 0.4912 0.4155 0.4681 0.060 Uiso 1 1 calc R . . H13B H 0.4977 0.5078 0.4130 0.060 Uiso 1 1 calc R . . H13C H 0.6060 0.4694 0.4530 0.060 Uiso 1 1 calc R . . C14 C 0.6088(2) 0.2796(2) 0.40082(15) 0.0461(7) Uani 1 1 d . . . H14A H 0.6213 0.2309 0.3620 0.069 Uiso 1 1 calc R . . H14B H 0.5586 0.2508 0.4366 0.069 Uiso 1 1 calc R . . H14C H 0.6786 0.2959 0.4241 0.069 Uiso 1 1 calc R . . C15 C 0.76601(16) 0.37204(16) 0.07549(11) 0.0180(4) Uani 1 1 d . . . C16 C 0.70016(16) 0.37410(15) 0.01408(11) 0.0204(5) Uani 1 1 d . . . C17 C 0.64797(16) 0.45847(16) -0.01178(12) 0.0226(5) Uani 1 1 d . . . C18 C 0.65639(17) 0.54762(16) 0.02473(12) 0.0227(5) Uani 1 1 d . . . C19 C 0.71753(17) 0.55027(16) 0.08698(12) 0.0223(5) Uani 1 1 d . . . C20 C 0.76859(16) 0.46443(16) 0.11032(11) 0.0199(5) Uani 1 1 d . . . C21 C 0.95426(16) 0.28757(15) 0.13495(11) 0.0179(5) Uani 1 1 d . . . C22 C 1.00756(16) 0.21019(16) 0.17113(11) 0.0200(5) Uani 1 1 d . . . C23 C 1.11270(17) 0.21526(17) 0.19702(11) 0.0247(5) Uani 1 1 d . . . C24 C 1.17209(17) 0.30067(18) 0.18712(12) 0.0259(5) Uani 1 1 d . . . C25 C 1.12609(17) 0.37883(17) 0.14951(12) 0.0245(5) Uani 1 1 d . . . C26 C 1.02139(16) 0.36979(15) 0.12293(11) 0.0193(5) Uani 1 1 d . . . C27 C 0.83945(16) 0.18254(15) 0.04550(11) 0.0201(5) Uani 1 1 d . . . C28 C 0.90112(17) 0.20409(16) -0.01601(12) 0.0225(5) Uani 1 1 d . . . C29 C 0.92692(17) 0.13590(18) -0.06873(12) 0.0260(5) Uani 1 1 d . . . C30 C 0.89168(18) 0.03870(18) -0.06246(13) 0.0286(5) Uani 1 1 d . . . C31 C 0.82984(19) 0.01238(16) -0.00391(13) 0.0291(5) Uani 1 1 d . . . C32 C 0.80409(17) 0.08405(16) 0.04788(12) 0.0224(5) Uani 1 1 d . . . B1 B 0.82633(19) 0.27105(17) 0.10786(13) 0.0181(5) Uani 1 1 d . . . H1 H 0.6129(17) 0.3560(16) 0.2210(12) 0.020(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0371(7) 0.0235(7) 0.0312(7) -0.0081(6) -0.0160(6) 0.0041(6) F2 0.0424(8) 0.0327(8) 0.0286(8) -0.0027(6) -0.0199(6) 0.0055(7) F3 0.0471(8) 0.0256(7) 0.0379(8) 0.0027(6) -0.0169(7) 0.0123(6) F4 0.0418(7) 0.0192(7) 0.0339(7) -0.0058(6) -0.0091(6) 0.0046(6) F5 0.0274(6) 0.0236(7) 0.0190(6) -0.0045(5) -0.0071(5) 0.0022(6) F6 0.0292(7) 0.0194(7) 0.0264(7) 0.0035(6) 0.0017(5) 0.0023(5) F7 0.0364(8) 0.0375(8) 0.0387(8) 0.0080(7) -0.0114(6) 0.0134(7) F8 0.0220(7) 0.0545(10) 0.0528(9) -0.0033(8) -0.0167(7) 0.0001(6) F9 0.0230(6) 0.0321(7) 0.0480(9) -0.0057(6) 0.0032(6) -0.0097(6) F10 0.0262(6) 0.0214(7) 0.0288(7) 0.0061(6) -0.0012(6) -0.0017(5) F11 0.0364(7) 0.0278(7) 0.0267(7) -0.0014(6) 0.0067(6) -0.0056(6) F12 0.0339(7) 0.0508(9) 0.0268(8) -0.0091(7) 0.0097(6) 0.0010(7) F13 0.0493(8) 0.0408(8) 0.0423(9) -0.0235(8) 0.0004(7) 0.0101(7) F14 0.0640(10) 0.0217(8) 0.0517(9) -0.0115(7) 0.0019(8) -0.0060(7) F15 0.0476(8) 0.0239(7) 0.0311(8) -0.0047(6) 0.0083(7) -0.0114(6) N1 0.0204(10) 0.0246(10) 0.0205(10) -0.0036(8) -0.0011(8) 0.0002(9) C1 0.0209(11) 0.0176(11) 0.0204(11) 0.0020(9) 0.0047(9) -0.0017(9) C2 0.0207(11) 0.0184(12) 0.0229(12) -0.0003(9) 0.0001(10) -0.0020(9) C3 0.0226(11) 0.0231(12) 0.0153(11) -0.0023(9) 0.0024(9) 0.0040(10) C4 0.0379(13) 0.0246(13) 0.0184(12) 0.0008(10) 0.0012(11) 0.0027(11) C5 0.0499(16) 0.0251(14) 0.0244(14) 0.0014(11) -0.0049(12) 0.0136(12) C6 0.0361(13) 0.0400(15) 0.0203(13) -0.0057(11) -0.0059(11) 0.0156(12) C7 0.0255(12) 0.0304(13) 0.0221(12) -0.0070(11) -0.0017(10) 0.0041(10) C8 0.0231(11) 0.0235(12) 0.0189(12) -0.0002(10) 0.0013(9) 0.0051(10) C9 0.0204(11) 0.0254(13) 0.0259(13) -0.0109(10) 0.0014(9) -0.0002(9) C10 0.0343(13) 0.0254(13) 0.0435(15) -0.0034(12) 0.0074(12) 0.0020(11) C11 0.0247(11) 0.0342(14) 0.0261(13) -0.0078(11) 0.0024(10) -0.0026(11) C12 0.0330(14) 0.0606(19) 0.0407(16) -0.0098(15) 0.0077(12) -0.0189(13) C13 0.0350(14) 0.0540(17) 0.0306(15) -0.0109(13) 0.0084(12) -0.0010(13) C14 0.0534(17) 0.0429(16) 0.0420(17) 0.0101(13) 0.0165(14) 0.0052(14) C15 0.0177(10) 0.0196(11) 0.0166(11) -0.0012(9) 0.0012(9) 0.0004(9) C16 0.0221(11) 0.0176(11) 0.0214(12) -0.0026(10) -0.0005(9) -0.0019(9) C17 0.0214(11) 0.0264(12) 0.0200(12) 0.0005(10) -0.0079(9) 0.0005(10) C18 0.0260(11) 0.0193(12) 0.0228(12) 0.0040(10) -0.0043(10) 0.0059(10) C19 0.0273(12) 0.0168(12) 0.0228(12) -0.0038(10) -0.0004(10) 0.0007(9) C20 0.0211(10) 0.0219(12) 0.0167(11) 0.0003(10) -0.0042(9) 0.0001(10) C21 0.0214(11) 0.0196(11) 0.0128(11) -0.0020(9) 0.0005(9) 0.0025(9) C22 0.0225(11) 0.0211(12) 0.0163(11) -0.0008(10) 0.0026(9) 0.0003(10) C23 0.0279(12) 0.0269(13) 0.0193(12) 0.0010(10) -0.0047(10) 0.0118(10) C24 0.0158(11) 0.0380(14) 0.0240(13) -0.0044(11) -0.0043(9) 0.0025(11) C25 0.0215(11) 0.0245(12) 0.0275(13) -0.0071(11) 0.0027(10) -0.0044(10) C26 0.0221(11) 0.0180(11) 0.0178(11) -0.0002(10) 0.0004(9) 0.0022(9) C27 0.0209(11) 0.0200(12) 0.0196(12) -0.0020(9) -0.0034(9) 0.0025(9) C28 0.0230(11) 0.0209(12) 0.0236(12) -0.0016(10) -0.0032(10) -0.0002(10) C29 0.0206(11) 0.0373(15) 0.0202(12) -0.0040(11) 0.0028(10) 0.0047(11) C30 0.0278(12) 0.0301(14) 0.0279(14) -0.0167(11) -0.0014(11) 0.0089(11) C31 0.0333(12) 0.0190(12) 0.0350(15) -0.0067(11) -0.0071(12) -0.0005(10) C32 0.0244(11) 0.0214(12) 0.0214(12) -0.0010(10) -0.0004(10) -0.0024(9) B1 0.0202(12) 0.0179(12) 0.0160(13) -0.0005(10) -0.0015(10) 0.0015(10) _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 C16 1.356(2) . ? F2 C17 1.347(2) . ? F3 C18 1.344(2) . ? F4 C19 1.349(2) . ? F5 C20 1.361(2) . ? F6 C22 1.363(2) . ? F7 C23 1.349(2) . ? F8 C24 1.349(2) . ? F9 C25 1.350(2) . ? F10 C26 1.356(2) . ? F11 C28 1.356(2) . ? F12 C29 1.361(2) . ? F13 C30 1.349(2) . ? F14 C31 1.348(2) . ? F15 C32 1.356(2) . ? N1 C1 1.305(3) . ? N1 C9 1.484(3) . ? N1 H1 0.89(2) . ? C1 C2 1.473(3) . ? C1 C3 1.488(3) . ? C2 B1 1.699(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C8 1.392(3) . ? C3 C4 1.392(3) . ? C4 C5 1.387(3) . ? C4 H4 0.9500 . ? C5 C6 1.375(3) . ? C5 H5 0.9500 . ? C6 C7 1.376(3) . ? C6 H6 0.9500 . ? C7 C8 1.398(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.528(3) . ? C9 C11 1.549(3) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.528(3) . ? C11 C13 1.534(3) . ? C11 C14 1.535(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C20 1.390(3) . ? C15 C16 1.393(3) . ? C15 B1 1.647(3) . ? C16 C17 1.378(3) . ? C17 C18 1.371(3) . ? C18 C19 1.373(3) . ? C19 C20 1.373(3) . ? C21 C26 1.387(3) . ? C21 C22 1.391(3) . ? C21 B1 1.656(3) . ? C22 C23 1.373(3) . ? C23 C24 1.362(3) . ? C24 C25 1.373(3) . ? C25 C26 1.376(3) . ? C27 C32 1.382(3) . ? C27 C28 1.395(3) . ? C27 B1 1.658(3) . ? C28 C29 1.370(3) . ? C29 C30 1.370(3) . ? C30 C31 1.367(3) . ? C31 C32 1.389(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 C1 N1 C9 130.60(19) . . ? C1 N1 H1 115.0(13) . . ? C9 N1 H1 114.4(13) . . ? N1 C1 C2 119.31(19) . . ? N1 C1 C3 121.52(19) . . ? C2 C1 C3 119.17(18) . . ? C1 C2 B1 116.13(16) . . ? C1 C2 H2A 108.3 . . ? B1 C2 H2A 108.3 . . ? C1 C2 H2B 108.3 . . ? B1 C2 H2B 108.3 . . ? H2A C2 H2B 107.4 . . ? C8 C3 C4 119.46(19) . . ? C8 C3 C1 122.51(19) . . ? C4 C3 C1 117.88(19) . . ? C5 C4 C3 120.2(2) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C6 C5 C4 120.1(2) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 120.4(2) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C6 C7 C8 120.2(2) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C3 C8 C7 119.6(2) . . ? C3 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? N1 C9 C10 106.96(18) . . ? N1 C9 C11 110.51(17) . . ? C10 C9 C11 115.06(18) . . ? N1 C9 H9 108.0 . . ? C10 C9 H9 108.0 . . ? C11 C9 H9 108.0 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C13 109.39(19) . . ? C12 C11 C14 109.6(2) . . ? C13 C11 C14 108.2(2) . . ? C12 C11 C9 112.00(19) . . ? C13 C11 C9 108.52(18) . . ? C14 C11 C9 109.04(18) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C20 C15 C16 111.97(18) . . ? C20 C15 B1 123.02(17) . . ? C16 C15 B1 124.84(18) . . ? F1 C16 C17 114.87(17) . . ? F1 C16 C15 120.60(18) . . ? C17 C16 C15 124.52(19) . . ? F2 C17 C18 119.76(18) . . ? F2 C17 C16 120.16(19) . . ? C18 C17 C16 120.07(19) . . ? F3 C18 C17 121.10(18) . . ? F3 C18 C19 120.42(18) . . ? C17 C18 C19 118.47(19) . . ? F4 C19 C20 121.01(19) . . ? F4 C19 C18 119.67(19) . . ? C20 C19 C18 119.32(19) . . ? F5 C20 C19 115.45(18) . . ? F5 C20 C15 118.95(18) . . ? C19 C20 C15 125.59(19) . . ? C26 C21 C22 112.71(18) . . ? C26 C21 B1 127.93(18) . . ? C22 C21 B1 119.27(18) . . ? F6 C22 C23 115.50(18) . . ? F6 C22 C21 119.78(17) . . ? C23 C22 C21 124.7(2) . . ? F7 C23 C24 120.31(19) . . ? F7 C23 C22 120.2(2) . . ? C24 C23 C22 119.5(2) . . ? F8 C24 C23 120.76(19) . . ? F8 C24 C25 120.3(2) . . ? C23 C24 C25 118.95(19) . . ? F9 C25 C24 120.03(18) . . ? F9 C25 C26 120.3(2) . . ? C24 C25 C26 119.7(2) . . ? F10 C26 C25 114.83(18) . . ? F10 C26 C21 120.99(17) . . ? C25 C26 C21 124.2(2) . . ? C32 C27 C28 112.96(19) . . ? C32 C27 B1 128.54(19) . . ? C28 C27 B1 118.29(18) . . ? F11 C28 C29 116.09(19) . . ? F11 C28 C27 119.23(18) . . ? C29 C28 C27 124.7(2) . . ? F12 C29 C30 119.51(19) . . ? F12 C29 C28 120.9(2) . . ? C30 C29 C28 119.6(2) . . ? F13 C30 C31 121.2(2) . . ? F13 C30 C29 119.9(2) . . ? C31 C30 C29 118.9(2) . . ? F14 C31 C30 119.9(2) . . ? F14 C31 C32 120.4(2) . . ? C30 C31 C32 119.7(2) . . ? F15 C32 C27 121.22(19) . . ? F15 C32 C31 114.71(18) . . ? C27 C32 C31 124.1(2) . . ? C15 B1 C21 115.07(17) . . ? C15 B1 C27 111.80(17) . . ? C21 B1 C27 102.36(16) . . ? C15 B1 C2 105.45(16) . . ? C21 B1 C2 110.41(16) . . ? C27 B1 C2 111.95(16) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.214 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.048 _chemical_absolute_configuration rm # Attachment 'zmh034.cif' data_zmh034_0m _database_code_depnum_ccdc_archive 'CCDC 809427' #TrackingRef 'zmh034.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C35 H19 B F15 N' _chemical_formula_sum 'C35 H19 B F15 N' _chemical_formula_weight 749.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' _symmetry_space_group_name_Hall 'P 2ac 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 12.2721(14) _cell_length_b 12.4428(15) _cell_length_c 20.360(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3109.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5332 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 21.24 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.13 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_max 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.601 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.156 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 48847 _diffrn_reflns_av_R_equivalents 0.1147 _diffrn_reflns_av_sigmaI/netI 0.0963 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 27.59 _reflns_number_total 7115 _reflns_number_gt 4477 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.1081P)^2^+0.5009P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(9) _refine_ls_number_reflns 7115 _refine_ls_number_parameters 475 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1239 _refine_ls_R_factor_gt 0.0693 _refine_ls_wR_factor_ref 0.1987 _refine_ls_wR_factor_gt 0.1733 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.3562(2) 0.5370(2) 0.84605(12) 0.0292(6) Uani 1 1 d . . . F2 F 0.2730(3) 0.3613(2) 0.89953(14) 0.0379(7) Uani 1 1 d . . . F3 F 0.1504(3) 0.3737(2) 1.01134(16) 0.0448(8) Uani 1 1 d . . . F4 F 0.1185(2) 0.5684(3) 1.06875(13) 0.0380(7) Uani 1 1 d . . . F5 F 0.1987(2) 0.7466(2) 1.01600(14) 0.0354(7) Uani 1 1 d . . . F6 F 0.4347(2) 0.7435(2) 1.02212(14) 0.0359(7) Uani 1 1 d . . . F7 F 0.4706(3) 0.8973(3) 1.11066(14) 0.0431(8) Uani 1 1 d . . . F8 F 0.4183(3) 1.1055(3) 1.08417(16) 0.0475(9) Uani 1 1 d . . . F9 F 0.3248(3) 1.1548(2) 0.96653(15) 0.0428(8) Uani 1 1 d . . . F10 F 0.2868(3) 1.0061(2) 0.87814(14) 0.0363(7) Uani 1 1 d . . . F11 F 0.5109(2) 0.5909(2) 0.92924(13) 0.0321(7) Uani 1 1 d . . . F12 F 0.7058(2) 0.5709(3) 0.87642(16) 0.0433(8) Uani 1 1 d . . . F13 F 0.7777(3) 0.7114(3) 0.78380(17) 0.0494(9) Uani 1 1 d . . . F14 F 0.6449(3) 0.8776(2) 0.74666(15) 0.0412(8) Uani 1 1 d . . . F15 F 0.4511(2) 0.9036(2) 0.80026(14) 0.0323(7) Uani 1 1 d . . . N1 N 0.1681(3) 0.6361(3) 0.78298(19) 0.0269(9) Uani 1 1 d . . . C1 C 0.2397(4) 0.7124(4) 0.7818(2) 0.0252(10) Uani 1 1 d . . . C2 C 0.2443(4) 0.7945(4) 0.8342(2) 0.0258(11) Uani 1 1 d . . . H2 H 0.2693 0.8629 0.8132 0.031 Uiso 1 1 calc R . . C3 C 0.1315(4) 0.8175(4) 0.8650(2) 0.0318(12) Uani 1 1 d . . . H3A H 0.1087 0.7555 0.8914 0.048 Uiso 1 1 calc R . . H3B H 0.0782 0.8302 0.8300 0.048 Uiso 1 1 calc R . . H3C H 0.1363 0.8812 0.8931 0.048 Uiso 1 1 calc R . . C4 C 0.3170(4) 0.7210(4) 0.7252(2) 0.0283(11) Uani 1 1 d . . . C5 C 0.3119(5) 0.8141(4) 0.6853(3) 0.0391(13) Uani 1 1 d . . . H5 H 0.2590 0.8680 0.6942 0.047 Uiso 1 1 calc R . . C6 C 0.3828(6) 0.8267(4) 0.6341(3) 0.0435(15) Uani 1 1 d . . . H6 H 0.3771 0.8882 0.6066 0.052 Uiso 1 1 calc R . . C7 C 0.4625(5) 0.7515(5) 0.6219(3) 0.0413(14) Uani 1 1 d . . . H7 H 0.5124 0.7617 0.5867 0.050 Uiso 1 1 calc R . . C8 C 0.4699(4) 0.6606(5) 0.6611(2) 0.0334(12) Uani 1 1 d . . . H8 H 0.5253 0.6089 0.6529 0.040 Uiso 1 1 calc R . . C9 C 0.3966(4) 0.6447(4) 0.7122(2) 0.0294(11) Uani 1 1 d . . . H9 H 0.4010 0.5815 0.7383 0.035 Uiso 1 1 calc R . . C10 C 0.1494(4) 0.5476(4) 0.7353(2) 0.0286(11) Uani 1 1 d . . . H10 H 0.2215 0.5232 0.7178 0.034 Uiso 1 1 calc R . . C11 C 0.0957(5) 0.4539(4) 0.7713(3) 0.0379(13) Uani 1 1 d . . . H11A H 0.0257 0.4773 0.7895 0.057 Uiso 1 1 calc R . . H11B H 0.1433 0.4297 0.8070 0.057 Uiso 1 1 calc R . . H11C H 0.0836 0.3945 0.7405 0.057 Uiso 1 1 calc R . . C12 C 0.0800(4) 0.5862(4) 0.6783(2) 0.0289(11) Uani 1 1 d . . . C13 C 0.1068(6) 0.5536(9) 0.6163(3) 0.078(3) Uani 1 1 d . . . H13 H 0.1700 0.5110 0.6093 0.094 Uiso 1 1 calc R . . C14 C 0.0417(7) 0.5829(11) 0.5636(3) 0.112(4) Uani 1 1 d . . . H14 H 0.0624 0.5621 0.5205 0.134 Uiso 1 1 calc R . . C15 C -0.0524(6) 0.6414(7) 0.5725(3) 0.0602(19) Uani 1 1 d . . . H15 H -0.0969 0.6607 0.5362 0.072 Uiso 1 1 calc R . . C16 C -0.0796(6) 0.6706(5) 0.6341(3) 0.0598(19) Uani 1 1 d . . . H16 H -0.1441 0.7112 0.6412 0.072 Uiso 1 1 calc R . . C17 C -0.0155(6) 0.6426(5) 0.6870(3) 0.0510(16) Uani 1 1 d . . . H17 H -0.0374 0.6625 0.7300 0.061 Uiso 1 1 calc R . . C18 C 0.2866(4) 0.6528(4) 0.9291(2) 0.0275(10) Uani 1 1 d . . . C19 C 0.2975(4) 0.5491(4) 0.9022(2) 0.0256(10) Uani 1 1 d . . . C20 C 0.2553(4) 0.4574(4) 0.9283(2) 0.0282(11) Uani 1 1 d . . . C21 C 0.1924(4) 0.4621(4) 0.9848(2) 0.0308(11) Uani 1 1 d . . . C22 C 0.1785(4) 0.5620(4) 1.0136(2) 0.0310(11) Uani 1 1 d . . . C23 C 0.2214(4) 0.6520(4) 0.9847(2) 0.0269(10) Uani 1 1 d . . . C24 C 0.3542(4) 0.8628(4) 0.9454(2) 0.0252(10) Uani 1 1 d . . . C25 C 0.4036(4) 0.8436(4) 1.0057(2) 0.0284(11) Uani 1 1 d . . . C26 C 0.4256(4) 0.9225(4) 1.0524(2) 0.0312(12) Uani 1 1 d . . . C27 C 0.3989(4) 1.0289(5) 1.0391(3) 0.0355(13) Uani 1 1 d . . . C28 C 0.3513(4) 1.0525(4) 0.9808(3) 0.0321(11) Uani 1 1 d . . . C29 C 0.3312(4) 0.9709(4) 0.9352(2) 0.0289(11) Uani 1 1 d . . . C30 C 0.4638(4) 0.7430(4) 0.8634(2) 0.0222(10) Uani 1 1 d . . . C31 C 0.5361(4) 0.6624(4) 0.8822(2) 0.0238(10) Uani 1 1 d . . . C32 C 0.6404(4) 0.6503(4) 0.8556(2) 0.0316(11) Uani 1 1 d . . . C33 C 0.6749(4) 0.7222(4) 0.8096(3) 0.0327(12) Uani 1 1 d . . . C34 C 0.6102(4) 0.8052(4) 0.7905(2) 0.0309(11) Uani 1 1 d . . . C35 C 0.5075(4) 0.8142(4) 0.8186(2) 0.0259(10) Uani 1 1 d . . . B1 B 0.3386(4) 0.7624(4) 0.8931(3) 0.0243(11) Uani 1 1 d . . . H1 H 0.122(5) 0.634(4) 0.821(3) 0.030(14) 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 F1 0.0348(16) 0.0278(15) 0.0251(13) -0.0032(12) 0.0063(12) -0.0005(13) F2 0.0515(19) 0.0260(15) 0.0361(16) -0.0044(12) 0.0037(15) -0.0007(14) F3 0.053(2) 0.0376(17) 0.0436(17) 0.0128(14) 0.0100(16) -0.0118(15) F4 0.0377(18) 0.0466(18) 0.0297(15) 0.0060(14) 0.0118(13) -0.0030(14) F5 0.0376(17) 0.0359(16) 0.0328(15) -0.0094(13) 0.0100(13) -0.0018(13) F6 0.0411(18) 0.0342(17) 0.0325(15) -0.0039(14) -0.0116(13) 0.0055(14) F7 0.056(2) 0.0436(19) 0.0302(15) -0.0092(14) -0.0142(15) 0.0051(15) F8 0.055(2) 0.0406(18) 0.0464(18) -0.0228(15) -0.0029(16) -0.0043(15) F9 0.056(2) 0.0251(16) 0.0469(18) -0.0025(13) -0.0041(16) 0.0016(15) F10 0.0490(19) 0.0300(15) 0.0299(15) -0.0001(12) -0.0060(14) 0.0044(14) F11 0.0359(17) 0.0302(16) 0.0303(14) 0.0066(12) -0.0013(13) 0.0028(13) F12 0.0310(17) 0.0402(18) 0.059(2) 0.0067(16) 0.0001(15) 0.0084(14) F13 0.0278(17) 0.054(2) 0.066(2) 0.0018(18) 0.0196(16) 0.0008(15) F14 0.0432(18) 0.0409(18) 0.0395(16) 0.0109(14) 0.0109(15) -0.0065(14) F15 0.0347(16) 0.0259(15) 0.0363(15) 0.0065(12) 0.0033(13) 0.0010(13) N1 0.029(2) 0.031(2) 0.0212(19) 0.0011(17) -0.0015(18) 0.0058(19) C1 0.028(3) 0.025(3) 0.023(2) 0.0008(19) -0.006(2) 0.009(2) C2 0.030(3) 0.025(3) 0.022(2) -0.0006(19) -0.002(2) 0.002(2) C3 0.032(3) 0.032(3) 0.032(3) -0.001(2) -0.003(2) 0.000(2) C4 0.030(3) 0.034(3) 0.020(2) -0.0026(19) -0.003(2) -0.003(2) C5 0.051(4) 0.035(3) 0.032(3) 0.000(2) 0.002(3) 0.005(3) C6 0.073(4) 0.030(3) 0.027(3) 0.006(2) 0.010(3) -0.005(3) C7 0.052(4) 0.040(3) 0.032(3) -0.003(3) 0.014(3) -0.013(3) C8 0.032(3) 0.038(3) 0.030(2) -0.004(2) 0.002(2) 0.001(2) C9 0.032(3) 0.029(3) 0.028(2) -0.001(2) -0.001(2) 0.000(2) C10 0.026(3) 0.029(3) 0.030(2) -0.008(2) -0.003(2) 0.008(2) C11 0.048(3) 0.032(3) 0.033(3) -0.007(2) -0.008(2) -0.001(3) C12 0.029(3) 0.030(3) 0.027(2) -0.006(2) 0.002(2) -0.001(2) C13 0.044(4) 0.157(8) 0.034(3) -0.024(5) -0.002(3) 0.021(5) C14 0.059(5) 0.252(14) 0.025(3) -0.014(6) -0.001(3) 0.001(7) C15 0.053(4) 0.082(5) 0.045(4) 0.012(4) -0.018(3) -0.013(4) C16 0.067(5) 0.047(4) 0.065(4) -0.008(3) -0.031(4) 0.013(3) C17 0.056(4) 0.057(4) 0.041(3) -0.011(3) -0.010(3) 0.026(3) C18 0.028(3) 0.029(3) 0.026(2) -0.002(2) -0.003(2) -0.003(2) C19 0.029(3) 0.030(3) 0.018(2) -0.0020(19) 0.000(2) 0.004(2) C20 0.036(3) 0.024(3) 0.025(2) -0.003(2) -0.005(2) 0.004(2) C21 0.030(3) 0.033(3) 0.030(2) 0.009(2) -0.002(2) -0.004(2) C22 0.026(3) 0.048(3) 0.019(2) 0.000(2) 0.002(2) 0.001(2) C23 0.032(3) 0.029(3) 0.020(2) -0.003(2) 0.003(2) 0.003(2) C24 0.018(2) 0.031(3) 0.027(2) 0.003(2) 0.001(2) -0.001(2) C25 0.032(3) 0.024(3) 0.030(3) -0.007(2) 0.002(2) -0.003(2) C26 0.028(3) 0.039(3) 0.027(3) -0.006(2) -0.003(2) -0.002(2) C27 0.033(3) 0.041(3) 0.032(3) -0.014(2) 0.001(2) -0.007(2) C28 0.033(3) 0.027(3) 0.037(3) 0.004(2) 0.009(2) 0.000(2) C29 0.033(3) 0.030(3) 0.024(2) 0.003(2) 0.002(2) -0.002(2) C30 0.025(2) 0.023(2) 0.018(2) -0.0038(18) -0.0026(19) -0.001(2) C31 0.029(3) 0.020(2) 0.022(2) -0.0041(19) 0.000(2) 0.000(2) C32 0.033(3) 0.028(3) 0.034(3) -0.004(2) -0.007(2) 0.006(2) C33 0.021(3) 0.039(3) 0.039(3) -0.008(2) 0.007(2) -0.003(2) C34 0.040(3) 0.029(3) 0.024(2) -0.005(2) 0.002(2) -0.008(2) C35 0.029(3) 0.026(3) 0.023(2) -0.0023(19) -0.007(2) -0.003(2) B1 0.025(3) 0.025(3) 0.023(3) 0.000(2) -0.002(2) -0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C19 1.359(5) . ? F2 C20 1.348(6) . ? F3 C21 1.329(6) . ? F4 C22 1.345(5) . ? F5 C23 1.367(5) . ? F6 C25 1.345(6) . ? F7 C26 1.345(6) . ? F8 C27 1.344(6) . ? F9 C28 1.345(6) . ? F10 C29 1.356(5) . ? F11 C31 1.343(5) . ? F12 C32 1.342(6) . ? F13 C33 1.374(6) . ? F14 C34 1.338(6) . ? F15 C35 1.362(5) . ? N1 C1 1.294(7) . ? N1 C10 1.486(6) . ? N1 H1 0.96(6) . ? C1 C2 1.479(7) . ? C1 C4 1.497(7) . ? C2 C3 1.546(7) . ? C2 B1 1.714(7) . ? C2 H2 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C9 1.387(7) . ? C4 C5 1.416(7) . ? C5 C6 1.368(8) . ? C5 H5 0.9500 . ? C6 C7 1.377(8) . ? C6 H6 0.9500 . ? C7 C8 1.387(8) . ? C7 H7 0.9500 . ? C8 C9 1.390(7) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C12 1.517(7) . ? C10 C11 1.527(8) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.367(8) . ? C12 C17 1.377(8) . ? C13 C14 1.386(11) . ? C13 H13 0.9500 . ? C14 C15 1.377(13) . ? C14 H14 0.9500 . ? C15 C16 1.348(10) . ? C15 H15 0.9500 . ? C16 C17 1.378(9) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C23 1.385(7) . ? C18 C19 1.409(7) . ? C18 B1 1.674(7) . ? C19 C20 1.361(7) . ? C20 C21 1.388(7) . ? C21 C22 1.384(7) . ? C22 C23 1.371(7) . ? C24 C25 1.390(7) . ? C24 C29 1.391(7) . ? C24 B1 1.653(7) . ? C25 C26 1.393(7) . ? C26 C27 1.391(8) . ? C27 C28 1.357(8) . ? C28 C29 1.396(7) . ? C30 C35 1.380(6) . ? C30 C31 1.393(7) . ? C30 B1 1.669(7) . ? C31 C32 1.399(7) . ? C32 C33 1.362(8) . ? C33 C34 1.360(8) . ? C34 C35 1.388(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C10 129.5(4) . . ? C1 N1 H1 116(3) . . ? C10 N1 H1 115(3) . . ? N1 C1 C2 121.3(4) . . ? N1 C1 C4 119.8(4) . . ? C2 C1 C4 118.8(4) . . ? C1 C2 C3 112.7(4) . . ? C1 C2 B1 111.7(4) . . ? C3 C2 B1 111.3(4) . . ? C1 C2 H2 106.9 . . ? C3 C2 H2 106.9 . . ? B1 C2 H2 106.9 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C9 C4 C5 118.9(5) . . ? C9 C4 C1 123.0(4) . . ? C5 C4 C1 118.1(4) . . ? C6 C5 C4 120.1(5) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 120.8(5) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C6 C7 C8 119.8(5) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C7 C8 C9 120.3(5) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C4 C9 C8 120.0(5) . . ? C4 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? N1 C10 C12 110.6(4) . . ? N1 C10 C11 108.6(4) . . ? C12 C10 C11 111.5(4) . . ? N1 C10 H10 108.7 . . ? C12 C10 H10 108.7 . . ? C11 C10 H10 108.7 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C17 118.3(5) . . ? C13 C12 C10 118.5(5) . . ? C17 C12 C10 122.8(4) . . ? C12 C13 C14 119.9(7) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C15 C14 C13 121.4(7) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C16 C15 C14 118.1(6) . . ? C16 C15 H15 120.9 . . ? C14 C15 H15 120.9 . . ? C15 C16 C17 121.2(7) . . ? C15 C16 H16 119.4 . . ? C17 C16 H16 119.4 . . ? C12 C17 C16 121.0(6) . . ? C12 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C23 C18 C19 111.5(4) . . ? C23 C18 B1 125.6(4) . . ? C19 C18 B1 122.7(4) . . ? F1 C19 C20 115.9(4) . . ? F1 C19 C18 118.6(4) . . ? C20 C19 C18 125.4(4) . . ? F2 C20 C19 120.9(4) . . ? F2 C20 C21 119.2(4) . . ? C19 C20 C21 120.0(4) . . ? F3 C21 C22 121.5(4) . . ? F3 C21 C20 121.1(5) . . ? C22 C21 C20 117.3(4) . . ? F4 C22 C23 121.4(5) . . ? F4 C22 C21 118.3(4) . . ? C23 C22 C21 120.3(4) . . ? F5 C23 C22 115.1(4) . . ? F5 C23 C18 119.5(4) . . ? C22 C23 C18 125.3(5) . . ? C25 C24 C29 112.8(4) . . ? C25 C24 B1 119.3(4) . . ? C29 C24 B1 127.7(4) . . ? F6 C25 C24 120.2(4) . . ? F6 C25 C26 115.4(4) . . ? C24 C25 C26 124.5(5) . . ? F7 C26 C27 119.4(4) . . ? F7 C26 C25 121.1(5) . . ? C27 C26 C25 119.5(5) . . ? F8 C27 C28 121.4(5) . . ? F8 C27 C26 120.1(5) . . ? C28 C27 C26 118.6(5) . . ? F9 C28 C27 119.8(5) . . ? F9 C28 C29 120.1(5) . . ? C27 C28 C29 120.0(5) . . ? F10 C29 C24 121.5(4) . . ? F10 C29 C28 113.9(4) . . ? C24 C29 C28 124.6(4) . . ? C35 C30 C31 113.3(4) . . ? C35 C30 B1 120.3(4) . . ? C31 C30 B1 126.2(4) . . ? F11 C31 C30 121.8(4) . . ? F11 C31 C32 114.6(4) . . ? C30 C31 C32 123.6(4) . . ? F12 C32 C33 121.0(5) . . ? F12 C32 C31 120.3(5) . . ? C33 C32 C31 118.7(5) . . ? C34 C33 C32 121.0(5) . . ? C34 C33 F13 120.1(5) . . ? C32 C33 F13 118.9(5) . . ? F14 C34 C33 121.1(5) . . ? F14 C34 C35 120.7(5) . . ? C33 C34 C35 118.2(5) . . ? F15 C35 C30 120.5(4) . . ? F15 C35 C34 114.5(4) . . ? C30 C35 C34 125.0(5) . . ? C24 B1 C30 103.7(4) . . ? C24 B1 C18 112.2(4) . . ? C30 B1 C18 113.1(4) . . ? C24 B1 C2 110.7(4) . . ? C30 B1 C2 113.6(4) . . ? C18 B1 C2 103.8(4) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.59 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.384 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.091 _chemical_absolute_configuration rm