# 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_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Douglas Stephan' _publ_contact_author_email dstephan@chem.utoronto.ca _publ_section_title ; Frustrated Lewis Pair Olefin Addition Reactions: P-, N-, C- and H-Based Nucleophilic Additions to an Olefin-Tethered Borane ; loop_ _publ_author_name 'Xiaoxi Zhao' D.Stephan # Attachment '- all-CIFs.txt' data_xz105_0m _database_code_depnum_ccdc_archive 'CCDC 870166' #TrackingRef '- all-CIFs.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H32 B F16 O P' _chemical_formula_weight 754.34 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.177(2) _cell_length_b 11.228(2) _cell_length_c 13.582(3) _cell_angle_alpha 69.214(10) _cell_angle_beta 82.733(11) _cell_angle_gamma 82.327(10) _cell_volume 1573.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2521 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 20.92 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.208 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9440 _exptl_absorpt_correction_T_max 0.9917 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 25270 _diffrn_reflns_av_R_equivalents 0.0791 _diffrn_reflns_av_sigmaI/netI 0.1303 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 27.55 _reflns_number_total 7056 _reflns_number_gt 3643 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0459P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7056 _refine_ls_number_parameters 452 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1447 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1213 _refine_ls_wR_factor_gt 0.0982 _refine_ls_goodness_of_fit_ref 0.982 _refine_ls_restrained_S_all 0.982 _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 P1 P 0.78474(7) 0.45455(7) 0.28574(6) 0.01620(19) Uani 1 1 d . . . F1 F 0.48375(15) 0.35329(15) 0.07424(13) 0.0276(4) Uani 1 1 d . . . F2 F 0.25685(16) 0.33631(17) 0.16083(15) 0.0396(5) Uani 1 1 d . . . F3 F 0.20443(16) 0.14629(19) 0.34807(16) 0.0450(5) Uani 1 1 d . . . F4 F 0.38405(17) -0.03581(17) 0.43871(15) 0.0425(5) Uani 1 1 d . . . F5 F 0.60864(16) -0.02598(16) 0.35290(14) 0.0346(5) Uani 1 1 d . . . F6 F 0.73864(16) 0.38456(15) -0.07693(13) 0.0297(5) Uani 1 1 d . . . F7 F 0.73596(16) 0.33840(16) -0.25477(13) 0.0314(5) Uani 1 1 d . . . F8 F 0.68217(17) 0.10888(16) -0.25230(13) 0.0343(5) Uani 1 1 d . . . F9 F 0.63381(18) -0.07985(16) -0.06303(14) 0.0362(5) Uani 1 1 d . . . F10 F 0.64333(17) -0.04040(15) 0.11794(13) 0.0326(5) Uani 1 1 d . . . F11 F 0.97411(17) 0.16276(18) 0.06143(15) 0.0388(5) Uani 1 1 d . . . F12 F 1.10478(16) 0.08841(19) 0.17729(16) 0.0442(5) Uani 1 1 d . . . F13 F 0.99928(18) -0.03975(17) 0.14660(16) 0.0465(6) Uani 1 1 d . . . F14 F 1.01818(18) -0.02333(17) 0.38005(16) 0.0434(5) Uani 1 1 d . . . F15 F 0.89160(18) -0.12881(16) 0.34590(15) 0.0404(5) Uani 1 1 d . . . F16 F 0.82729(17) 0.00979(16) 0.42129(14) 0.0349(5) Uani 1 1 d . . . O1 O 0.78424(18) 0.07987(17) 0.20990(15) 0.0206(5) Uani 1 1 d . . . C1 C 0.5608(3) 0.1686(3) 0.2100(2) 0.0171(7) Uani 1 1 d . . . C2 C 0.4640(3) 0.2547(3) 0.1671(2) 0.0211(7) Uani 1 1 d . . . C3 C 0.3463(3) 0.2491(3) 0.2097(3) 0.0272(8) Uani 1 1 d . . . C4 C 0.3195(3) 0.1527(3) 0.3036(3) 0.0288(8) Uani 1 1 d . . . C5 C 0.4100(3) 0.0633(3) 0.3495(2) 0.0261(8) Uani 1 1 d . . . C6 C 0.5268(3) 0.0709(3) 0.3025(2) 0.0245(8) Uani 1 1 d . . . C7 C 0.6943(3) 0.1731(3) 0.0318(2) 0.0180(7) Uani 1 1 d . . . C8 C 0.7145(3) 0.2646(3) -0.0669(2) 0.0200(7) Uani 1 1 d . . . C9 C 0.7121(3) 0.2447(3) -0.1609(2) 0.0206(7) Uani 1 1 d . . . C10 C 0.6853(3) 0.1289(3) -0.1604(2) 0.0236(8) Uani 1 1 d . . . C11 C 0.6623(3) 0.0340(3) -0.0653(3) 0.0230(7) Uani 1 1 d . . . C12 C 0.6673(3) 0.0580(3) 0.0273(2) 0.0205(7) Uani 1 1 d . . . C13 C 0.8922(3) 0.0948(3) 0.2396(2) 0.0207(7) Uani 1 1 d . . . C14 C 0.9060(3) 0.2237(3) 0.2555(2) 0.0210(7) Uani 1 1 d . . . H14A H 0.9382 0.2050 0.3246 0.025 Uiso 1 1 calc R . . H14B H 0.9648 0.2720 0.1995 0.025 Uiso 1 1 calc R . . C15 C 0.7832(3) 0.3068(3) 0.2516(2) 0.0180(7) Uani 1 1 d . . . H15A H 0.7260 0.2522 0.3065 0.022 Uiso 1 1 calc R . . C16 C 0.7380(3) 0.3253(3) 0.1434(2) 0.0185(7) Uani 1 1 d . . . H16A H 0.8033 0.3538 0.0862 0.022 Uiso 1 1 calc R . . H16B H 0.6679 0.3911 0.1288 0.022 Uiso 1 1 calc R . . C17 C 0.9931(3) 0.0746(3) 0.1569(3) 0.0272(8) Uani 1 1 d . . . C18 C 0.9075(3) -0.0131(3) 0.3471(3) 0.0286(8) Uani 1 1 d . . . C19 C 0.9268(3) 0.5356(3) 0.2249(2) 0.0262(8) Uani 1 1 d . . . C20 C 0.9548(3) 0.5413(3) 0.1098(2) 0.0306(8) Uani 1 1 d . . . H20A H 1.0270 0.5868 0.0788 0.046 Uiso 1 1 calc R . . H20B H 0.8858 0.5866 0.0693 0.046 Uiso 1 1 calc R . . H20C H 0.9696 0.4541 0.1078 0.046 Uiso 1 1 calc R . . C21 C 1.0376(3) 0.4605(3) 0.2862(3) 0.0332(9) Uani 1 1 d . . . H21A H 1.1113 0.5009 0.2507 0.050 Uiso 1 1 calc R . . H21B H 1.0458 0.3719 0.2878 0.050 Uiso 1 1 calc R . . H21C H 1.0255 0.4616 0.3586 0.050 Uiso 1 1 calc R . . C22 C 0.9179(3) 0.6742(3) 0.2262(3) 0.0355(9) Uani 1 1 d . . . H22A H 0.9960 0.7095 0.1993 0.053 Uiso 1 1 calc R . . H22B H 0.8971 0.6732 0.2987 0.053 Uiso 1 1 calc R . . H22C H 0.8550 0.7273 0.1813 0.053 Uiso 1 1 calc R . . C23 C 0.7754(3) 0.4001(3) 0.4352(2) 0.0235(7) Uani 1 1 d . . . C24 C 0.8589(3) 0.2774(3) 0.4836(2) 0.0305(8) Uani 1 1 d . . . H24A H 0.8544 0.2560 0.5604 0.046 Uiso 1 1 calc R . . H24B H 0.9425 0.2913 0.4537 0.046 Uiso 1 1 calc R . . H24C H 0.8330 0.2068 0.4675 0.046 Uiso 1 1 calc R . . C25 C 0.8045(3) 0.5033(3) 0.4762(2) 0.0285(8) Uani 1 1 d . . . H25A H 0.7894 0.4739 0.5534 0.043 Uiso 1 1 calc R . . H25B H 0.7529 0.5826 0.4452 0.043 Uiso 1 1 calc R . . H25C H 0.8898 0.5194 0.4562 0.043 Uiso 1 1 calc R . . C26 C 0.6452(3) 0.3634(3) 0.4808(3) 0.0336(9) Uani 1 1 d . . . H26A H 0.6428 0.3253 0.5580 0.050 Uiso 1 1 calc R . . H26B H 0.6231 0.3015 0.4520 0.050 Uiso 1 1 calc R . . H26C H 0.5878 0.4403 0.4612 0.050 Uiso 1 1 calc R . . C27 C 0.6459(3) 0.5664(3) 0.2370(2) 0.0253(8) Uani 1 1 d . . . C28 C 0.6140(3) 0.6688(3) 0.2910(3) 0.0294(8) Uani 1 1 d . . . H28A H 0.5407 0.7227 0.2634 0.044 Uiso 1 1 calc R . . H28B H 0.6813 0.7220 0.2760 0.044 Uiso 1 1 calc R . . H28C H 0.5996 0.6263 0.3675 0.044 Uiso 1 1 calc R . . C29 C 0.5344(3) 0.4880(3) 0.2584(3) 0.0318(8) Uani 1 1 d . . . H29A H 0.4854 0.5224 0.1977 0.048 Uiso 1 1 calc R . . H29B H 0.4852 0.4942 0.3218 0.048 Uiso 1 1 calc R . . H29C H 0.5624 0.3981 0.2692 0.048 Uiso 1 1 calc R . . C30 C 0.6625(3) 0.6418(3) 0.1162(2) 0.0331(9) Uani 1 1 d . . . H30A H 0.5865 0.6930 0.0928 0.050 Uiso 1 1 calc R . . H30B H 0.6845 0.5815 0.0780 0.050 Uiso 1 1 calc R . . H30C H 0.7269 0.6985 0.1017 0.050 Uiso 1 1 calc R . . B1 B 0.6985(3) 0.1880(3) 0.1488(3) 0.0190(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0189(4) 0.0137(4) 0.0155(4) -0.0053(3) -0.0009(3) 0.0006(3) F1 0.0272(11) 0.0257(10) 0.0248(11) -0.0027(8) -0.0017(8) -0.0017(8) F2 0.0214(11) 0.0406(12) 0.0503(13) -0.0106(10) -0.0014(9) 0.0035(9) F3 0.0251(12) 0.0596(14) 0.0480(14) -0.0194(11) 0.0135(10) -0.0096(10) F4 0.0417(13) 0.0420(13) 0.0341(12) -0.0018(10) 0.0094(9) -0.0148(10) F5 0.0337(12) 0.0287(11) 0.0297(12) 0.0026(9) -0.0006(9) -0.0008(9) F6 0.0475(13) 0.0194(10) 0.0223(10) -0.0041(8) -0.0031(8) -0.0122(9) F7 0.0421(12) 0.0277(11) 0.0197(11) -0.0021(8) -0.0006(8) -0.0057(9) F8 0.0503(13) 0.0369(12) 0.0217(11) -0.0174(9) -0.0071(9) -0.0005(9) F9 0.0593(14) 0.0231(11) 0.0333(12) -0.0148(9) -0.0067(10) -0.0116(9) F10 0.0562(14) 0.0191(10) 0.0218(11) -0.0030(8) -0.0004(9) -0.0158(9) F11 0.0420(13) 0.0419(12) 0.0299(12) -0.0130(10) 0.0112(9) -0.0063(10) F12 0.0195(12) 0.0542(14) 0.0660(15) -0.0336(12) 0.0020(10) 0.0034(9) F13 0.0521(14) 0.0295(12) 0.0635(15) -0.0299(11) 0.0158(11) -0.0038(10) F14 0.0414(13) 0.0299(12) 0.0540(14) -0.0049(10) -0.0246(10) 0.0060(9) F15 0.0595(15) 0.0172(11) 0.0434(13) -0.0064(9) -0.0138(10) -0.0025(9) F16 0.0443(13) 0.0319(11) 0.0237(11) -0.0045(9) 0.0005(9) -0.0049(9) O1 0.0202(12) 0.0160(11) 0.0260(12) -0.0062(9) -0.0065(9) -0.0013(9) C1 0.0206(17) 0.0186(17) 0.0163(17) -0.0111(14) 0.0006(13) -0.0043(13) C2 0.0259(19) 0.0196(18) 0.0188(18) -0.0080(15) 0.0034(14) -0.0066(14) C3 0.0214(19) 0.029(2) 0.032(2) -0.0134(17) -0.0013(15) 0.0008(15) C4 0.022(2) 0.038(2) 0.032(2) -0.0197(18) 0.0105(16) -0.0108(17) C5 0.030(2) 0.0235(19) 0.0241(19) -0.0074(15) 0.0078(15) -0.0124(16) C6 0.027(2) 0.0228(19) 0.0248(19) -0.0095(15) 0.0009(15) -0.0045(15) C7 0.0160(17) 0.0165(17) 0.0215(18) -0.0078(14) -0.0005(13) 0.0007(13) C8 0.0186(18) 0.0172(17) 0.0249(19) -0.0086(14) 0.0006(13) -0.0024(13) C9 0.0206(18) 0.0208(18) 0.0159(18) -0.0014(14) -0.0002(13) -0.0015(14) C10 0.0197(18) 0.032(2) 0.023(2) -0.0156(16) -0.0018(14) 0.0015(15) C11 0.0273(19) 0.0173(18) 0.028(2) -0.0130(15) -0.0006(15) -0.0023(14) C12 0.0242(19) 0.0171(17) 0.0168(18) -0.0022(14) -0.0005(13) -0.0014(14) C13 0.0174(18) 0.0181(17) 0.0272(19) -0.0093(14) -0.0021(14) 0.0002(13) C14 0.0182(18) 0.0190(17) 0.0261(19) -0.0096(14) -0.0008(14) 0.0017(13) C15 0.0213(18) 0.0123(16) 0.0213(18) -0.0063(13) -0.0025(13) -0.0019(13) C16 0.0200(17) 0.0176(17) 0.0177(17) -0.0066(13) -0.0010(13) -0.0005(13) C17 0.027(2) 0.0211(19) 0.037(2) -0.0153(17) 0.0002(16) -0.0008(15) C18 0.030(2) 0.021(2) 0.035(2) -0.0082(16) -0.0110(17) 0.0023(15) C19 0.029(2) 0.0237(19) 0.029(2) -0.0124(15) 0.0042(15) -0.0098(15) C20 0.037(2) 0.0253(19) 0.030(2) -0.0127(16) 0.0162(16) -0.0124(16) C21 0.025(2) 0.036(2) 0.044(2) -0.0210(18) 0.0039(16) -0.0072(16) C22 0.044(2) 0.026(2) 0.040(2) -0.0172(17) 0.0093(18) -0.0131(17) C23 0.030(2) 0.0230(18) 0.0170(18) -0.0078(14) -0.0027(14) 0.0030(14) C24 0.043(2) 0.0256(19) 0.0194(19) -0.0045(15) -0.0079(16) 0.0067(16) C25 0.039(2) 0.0293(19) 0.0205(19) -0.0137(15) -0.0061(15) 0.0037(16) C26 0.038(2) 0.030(2) 0.026(2) -0.0062(16) 0.0099(16) -0.0015(16) C27 0.029(2) 0.0182(17) 0.030(2) -0.0120(15) -0.0080(15) 0.0068(14) C28 0.030(2) 0.0219(19) 0.036(2) -0.0117(16) -0.0080(16) 0.0099(15) C29 0.023(2) 0.033(2) 0.041(2) -0.0171(17) -0.0045(16) 0.0064(15) C30 0.049(2) 0.0182(18) 0.029(2) -0.0057(15) -0.0136(17) 0.0086(16) B1 0.024(2) 0.0159(19) 0.018(2) -0.0058(16) 0.0005(15) -0.0068(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 P1 C15 1.877(3) . ? P1 C19 1.885(3) . ? P1 C27 1.890(3) . ? P1 C23 1.894(3) . ? F1 C2 1.367(3) . ? F2 C3 1.358(4) . ? F3 C4 1.350(3) . ? F4 C5 1.353(3) . ? F5 C6 1.361(3) . ? F6 C8 1.365(3) . ? F7 C9 1.356(3) . ? F8 C10 1.349(3) . ? F9 C11 1.347(3) . ? F10 C12 1.356(3) . ? F11 C17 1.345(4) . ? F12 C17 1.353(4) . ? F13 C17 1.331(3) . ? F14 C18 1.345(4) . ? F15 C18 1.341(3) . ? F16 C18 1.334(4) . ? O1 C13 1.368(3) . ? O1 B1 1.502(4) . ? C1 C2 1.388(4) . ? C1 C6 1.393(4) . ? C1 B1 1.657(4) . ? C2 C3 1.369(4) . ? C3 C4 1.377(4) . ? C4 C5 1.365(5) . ? C5 C6 1.379(4) . ? C7 C8 1.382(4) . ? C7 C12 1.390(4) . ? C7 B1 1.662(5) . ? C8 C9 1.377(4) . ? C9 C10 1.371(4) . ? C10 C11 1.371(4) . ? C11 C12 1.386(4) . ? C13 C17 1.542(4) . ? C13 C18 1.543(4) . ? C13 C14 1.567(4) . ? C14 C15 1.549(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.549(4) . ? C15 H15A 1.0000 . ? C16 B1 1.634(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C19 C20 1.535(4) . ? C19 C22 1.552(4) . ? C19 C21 1.556(4) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C25 1.539(4) . ? C23 C24 1.540(4) . ? C23 C26 1.556(4) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.552(4) . ? C27 C30 1.557(4) . ? C27 C29 1.560(4) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 P1 C19 110.91(13) . . ? C15 P1 C27 108.62(13) . . ? C19 P1 C27 110.52(14) . . ? C15 P1 C23 106.21(13) . . ? C19 P1 C23 111.17(14) . . ? C27 P1 C23 109.28(14) . . ? C13 O1 B1 124.5(2) . . ? C2 C1 C6 113.1(3) . . ? C2 C1 B1 119.5(3) . . ? C6 C1 B1 127.4(3) . . ? F1 C2 C3 115.5(3) . . ? F1 C2 C1 119.4(3) . . ? C3 C2 C1 125.2(3) . . ? F2 C3 C2 121.0(3) . . ? F2 C3 C4 120.2(3) . . ? C2 C3 C4 118.8(3) . . ? F3 C4 C5 120.8(3) . . ? F3 C4 C3 119.9(3) . . ? C5 C4 C3 119.3(3) . . ? F4 C5 C4 120.0(3) . . ? F4 C5 C6 119.9(3) . . ? C4 C5 C6 120.0(3) . . ? F5 C6 C5 115.0(3) . . ? F5 C6 C1 121.4(3) . . ? C5 C6 C1 123.6(3) . . ? C8 C7 C12 113.0(3) . . ? C8 C7 B1 127.5(3) . . ? C12 C7 B1 119.5(3) . . ? F6 C8 C9 114.8(3) . . ? F6 C8 C7 120.7(3) . . ? C9 C8 C7 124.4(3) . . ? F7 C9 C10 119.2(3) . . ? F7 C9 C8 120.9(3) . . ? C10 C9 C8 119.9(3) . . ? F8 C10 C9 120.3(3) . . ? F8 C10 C11 120.8(3) . . ? C9 C10 C11 119.0(3) . . ? F9 C11 C10 119.9(3) . . ? F9 C11 C12 121.0(3) . . ? C10 C11 C12 119.0(3) . . ? F10 C12 C11 115.5(2) . . ? F10 C12 C7 119.8(3) . . ? C11 C12 C7 124.6(3) . . ? O1 C13 C17 107.8(2) . . ? O1 C13 C18 105.0(2) . . ? C17 C13 C18 109.9(3) . . ? O1 C13 C14 118.2(2) . . ? C17 C13 C14 108.6(2) . . ? C18 C13 C14 107.1(2) . . ? C15 C14 C13 111.4(2) . . ? C15 C14 H14A 109.3 . . ? C13 C14 H14A 109.3 . . ? C15 C14 H14B 109.3 . . ? C13 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? C14 C15 C16 105.3(2) . . ? C14 C15 P1 115.21(19) . . ? C16 C15 P1 117.00(19) . . ? C14 C15 H15A 106.2 . . ? C16 C15 H15A 106.2 . . ? P1 C15 H15A 106.2 . . ? C15 C16 B1 107.8(2) . . ? C15 C16 H16A 110.1 . . ? B1 C16 H16A 110.1 . . ? C15 C16 H16B 110.1 . . ? B1 C16 H16B 110.1 . . ? H16A C16 H16B 108.5 . . ? F13 C17 F11 107.0(3) . . ? F13 C17 F12 106.7(3) . . ? F11 C17 F12 105.8(2) . . ? F13 C17 C13 113.7(3) . . ? F11 C17 C13 109.8(3) . . ? F12 C17 C13 113.3(3) . . ? F16 C18 F15 107.1(3) . . ? F16 C18 F14 107.0(3) . . ? F15 C18 F14 106.4(3) . . ? F16 C18 C13 110.3(3) . . ? F15 C18 C13 113.3(3) . . ? F14 C18 C13 112.4(3) . . ? C20 C19 C22 108.1(2) . . ? C20 C19 C21 107.5(3) . . ? C22 C19 C21 107.0(3) . . ? C20 C19 P1 110.8(2) . . ? C22 C19 P1 112.6(2) . . ? C21 C19 P1 110.7(2) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C25 C23 C24 108.5(3) . . ? C25 C23 C26 108.3(3) . . ? C24 C23 C26 104.8(2) . . ? C25 C23 P1 113.0(2) . . ? C24 C23 P1 112.6(2) . . ? C26 C23 P1 109.3(2) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 C30 106.0(2) . . ? C28 C27 C29 107.8(3) . . ? C30 C27 C29 108.0(3) . . ? C28 C27 P1 113.3(2) . . ? C30 C27 P1 111.8(2) . . ? C29 C27 P1 109.7(2) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O1 B1 C16 110.5(2) . . ? O1 B1 C1 108.3(2) . . ? C16 B1 C1 109.0(2) . . ? O1 B1 C7 107.2(2) . . ? C16 B1 C7 114.7(2) . . ? C1 B1 C7 106.8(2) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.328 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.072 #===end data_xz110_0ma _database_code_depnum_ccdc_archive 'CCDC 870167' #TrackingRef '- all-CIFs.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H14 B F16 O P' _chemical_formula_weight 628.10 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.1479(8) _cell_length_b 9.9549(5) _cell_length_c 15.5394(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.713(2) _cell_angle_gamma 90.00 _cell_volume 2351.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6546 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 29.47 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.774 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.259 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9428 _exptl_absorpt_correction_T_max 0.9721 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25071 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 29.71 _reflns_number_total 6659 _reflns_number_gt 5041 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+1.0295P] 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 6659 _refine_ls_number_parameters 364 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1133 _refine_ls_wR_factor_gt 0.1032 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 P1 P 0.28262(3) 0.63933(4) 0.18771(3) 0.02424(10) Uani 1 1 d . . . F1 F 0.34666(7) 0.98889(11) 0.46426(6) 0.0325(2) Uani 1 1 d . . . F2 F 0.47238(8) 1.12200(12) 0.59155(7) 0.0414(3) Uani 1 1 d . . . F3 F 0.55295(8) 1.33721(13) 0.54490(9) 0.0505(3) Uani 1 1 d . . . F4 F 0.50255(8) 1.41590(12) 0.36699(9) 0.0474(3) Uani 1 1 d . . . F5 F 0.37657(8) 1.29079(11) 0.23928(7) 0.0357(3) Uani 1 1 d . . . F6 F 0.18032(9) 0.83094(12) 0.35154(8) 0.0439(3) Uani 1 1 d . . . F7 F 0.03909(10) 0.87821(17) 0.39721(10) 0.0662(4) Uani 1 1 d . . . F8 F -0.03801(9) 1.1261(2) 0.37155(11) 0.0764(5) Uani 1 1 d . . . F9 F 0.03356(9) 1.32800(15) 0.30257(9) 0.0590(4) Uani 1 1 d . . . F10 F 0.17645(7) 1.28564(10) 0.25838(8) 0.0368(3) Uani 1 1 d . . . F11 F 0.36333(8) 1.10814(12) 0.08036(9) 0.0468(3) Uani 1 1 d . . . F12 F 0.25367(9) 1.23960(11) 0.02443(8) 0.0455(3) Uani 1 1 d . . . F13 F 0.26073(11) 1.05559(14) -0.04423(8) 0.0619(4) Uani 1 1 d . . . F14 F 0.10180(9) 1.17404(14) 0.04651(11) 0.0597(4) Uani 1 1 d . . . F15 F 0.10172(10) 1.00224(17) -0.03594(9) 0.0681(4) Uani 1 1 d . . . F16 F 0.08828(8) 0.97739(14) 0.09633(9) 0.0515(3) Uani 1 1 d . . . O1 O 0.25524(8) 1.10367(11) 0.17792(7) 0.0238(2) Uani 1 1 d . . . C1 C 0.35311(10) 1.13166(16) 0.34410(10) 0.0211(3) Uani 1 1 d . . . C2 C 0.38301(11) 1.09589(17) 0.43612(11) 0.0240(3) Uani 1 1 d . . . C3 C 0.44872(11) 1.16193(18) 0.50384(11) 0.0291(4) Uani 1 1 d . . . C4 C 0.48905(11) 1.27082(19) 0.48079(13) 0.0325(4) Uani 1 1 d . . . C5 C 0.46280(11) 1.31082(18) 0.39104(13) 0.0306(4) Uani 1 1 d . . . C6 C 0.39632(11) 1.24174(17) 0.32536(11) 0.0249(3) Uani 1 1 d . . . C7 C 0.18595(11) 1.05562(17) 0.30027(10) 0.0235(3) Uani 1 1 d . . . C8 C 0.14684(12) 0.9577(2) 0.33678(11) 0.0318(4) Uani 1 1 d . . . C9 C 0.07279(13) 0.9790(2) 0.36156(13) 0.0429(5) Uani 1 1 d . . . C10 C 0.03460(13) 1.1032(3) 0.34930(14) 0.0470(6) Uani 1 1 d . . . C11 C 0.06998(13) 1.2051(2) 0.31365(13) 0.0392(5) Uani 1 1 d . . . C12 C 0.14425(11) 1.17967(19) 0.29090(11) 0.0287(4) Uani 1 1 d . . . C13 C 0.23009(11) 1.03532(17) 0.09579(10) 0.0251(3) Uani 1 1 d . . . C14 C 0.25665(12) 0.88526(17) 0.09832(11) 0.0266(3) Uani 1 1 d . . . H14A H 0.2169 0.8393 0.0434 0.032 Uiso 1 1 calc R . . H14B H 0.3173 0.8787 0.0967 0.032 Uiso 1 1 calc R . . C15 C 0.25214(11) 0.81429(16) 0.18441(10) 0.0228(3) Uani 1 1 d . . . H15A H 0.1902 0.8196 0.1841 0.027 Uiso 1 1 calc R . . C16 C 0.31181(11) 0.89006(15) 0.26923(10) 0.0225(3) Uani 1 1 d . . . H16A H 0.3727 0.8933 0.2680 0.027 Uiso 1 1 calc R . . H16B H 0.3128 0.8422 0.3254 0.027 Uiso 1 1 calc R . . C17 C 0.27650(14) 1.11046(19) 0.03822(12) 0.0347(4) Uani 1 1 d . . . C18 C 0.12960(14) 1.0483(2) 0.05002(14) 0.0408(5) Uani 1 1 d . . . C19 C 0.21769(13) 0.5507(2) 0.08788(13) 0.0381(4) Uani 1 1 d . . . H19A H 0.2293 0.4542 0.0968 0.057 Uiso 1 1 calc R . . H19B H 0.2329 0.5813 0.0352 0.057 Uiso 1 1 calc R . . H19C H 0.1552 0.5680 0.0769 0.057 Uiso 1 1 calc R . . C20 C 0.39579(12) 0.62306(19) 0.19758(14) 0.0337(4) Uani 1 1 d . . . H20A H 0.4115 0.5277 0.2004 0.050 Uiso 1 1 calc R . . H20B H 0.4327 0.6682 0.2534 0.050 Uiso 1 1 calc R . . H20C H 0.4051 0.6644 0.1444 0.050 Uiso 1 1 calc R . . C21 C 0.26513(13) 0.56513(18) 0.28431(12) 0.0330(4) Uani 1 1 d . . . H21A H 0.2794 0.4692 0.2866 0.050 Uiso 1 1 calc R . . H21B H 0.2034 0.5762 0.2793 0.050 Uiso 1 1 calc R . . H21C H 0.3030 0.6091 0.3402 0.050 Uiso 1 1 calc R . . B1 B 0.27507(12) 1.04136(18) 0.26997(11) 0.0205(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0283(2) 0.0214(2) 0.0252(2) -0.00316(15) 0.01197(16) -0.00273(16) F1 0.0381(6) 0.0366(6) 0.0236(5) 0.0032(4) 0.0117(4) -0.0072(4) F2 0.0419(6) 0.0520(7) 0.0232(5) -0.0034(5) 0.0019(5) 0.0019(5) F3 0.0370(7) 0.0485(7) 0.0511(7) -0.0156(6) -0.0046(5) -0.0113(5) F4 0.0422(7) 0.0355(6) 0.0615(8) -0.0030(6) 0.0137(6) -0.0186(5) F5 0.0451(6) 0.0304(6) 0.0325(5) 0.0049(4) 0.0141(5) -0.0104(5) F6 0.0604(8) 0.0354(6) 0.0451(7) 0.0042(5) 0.0300(6) -0.0112(5) F7 0.0596(9) 0.0978(12) 0.0543(8) 0.0030(8) 0.0364(7) -0.0345(8) F8 0.0361(7) 0.1388(16) 0.0682(10) -0.0075(10) 0.0359(7) 0.0046(8) F9 0.0465(8) 0.0769(10) 0.0523(8) -0.0096(7) 0.0151(6) 0.0308(7) F10 0.0415(6) 0.0256(5) 0.0463(6) -0.0018(4) 0.0186(5) 0.0030(5) F11 0.0457(7) 0.0426(7) 0.0670(8) 0.0161(6) 0.0386(6) 0.0072(5) F12 0.0675(8) 0.0322(6) 0.0473(7) 0.0175(5) 0.0332(6) 0.0134(6) F13 0.1152(13) 0.0530(8) 0.0314(6) 0.0010(5) 0.0428(7) 0.0036(8) F14 0.0389(7) 0.0523(8) 0.0796(10) 0.0136(7) 0.0092(7) 0.0183(6) F15 0.0559(9) 0.0925(12) 0.0342(7) -0.0048(7) -0.0132(6) 0.0047(8) F16 0.0262(6) 0.0619(9) 0.0617(8) 0.0088(6) 0.0088(6) -0.0025(5) O1 0.0311(6) 0.0223(6) 0.0203(5) 0.0009(4) 0.0118(5) 0.0006(5) C1 0.0205(7) 0.0214(7) 0.0241(7) -0.0024(6) 0.0111(6) 0.0013(6) C2 0.0239(8) 0.0250(8) 0.0254(7) -0.0015(6) 0.0113(6) 0.0009(6) C3 0.0258(8) 0.0348(10) 0.0241(8) -0.0050(7) 0.0048(6) 0.0062(7) C4 0.0220(8) 0.0341(10) 0.0373(9) -0.0131(7) 0.0045(7) -0.0002(7) C5 0.0253(8) 0.0242(8) 0.0435(10) -0.0042(7) 0.0131(7) -0.0038(7) C6 0.0250(8) 0.0234(8) 0.0282(8) -0.0016(6) 0.0115(6) 0.0001(6) C7 0.0242(8) 0.0288(8) 0.0187(7) -0.0050(6) 0.0091(6) -0.0047(6) C8 0.0341(9) 0.0403(10) 0.0237(8) -0.0034(7) 0.0134(7) -0.0089(8) C9 0.0348(10) 0.0674(15) 0.0323(9) -0.0031(9) 0.0186(8) -0.0200(10) C10 0.0247(9) 0.0867(18) 0.0350(10) -0.0095(10) 0.0168(8) -0.0027(10) C11 0.0286(9) 0.0559(13) 0.0311(9) -0.0098(8) 0.0077(8) 0.0107(9) C12 0.0248(8) 0.0367(10) 0.0254(8) -0.0063(7) 0.0097(7) -0.0011(7) C13 0.0281(8) 0.0288(9) 0.0186(7) 0.0025(6) 0.0081(6) 0.0003(6) C14 0.0347(9) 0.0261(9) 0.0196(7) -0.0008(6) 0.0100(6) 0.0008(7) C15 0.0260(8) 0.0225(8) 0.0205(7) -0.0008(6) 0.0086(6) 0.0001(6) C16 0.0258(8) 0.0223(8) 0.0186(7) -0.0012(6) 0.0066(6) 0.0001(6) C17 0.0531(12) 0.0303(10) 0.0288(8) 0.0060(7) 0.0247(8) 0.0073(8) C18 0.0347(10) 0.0455(12) 0.0353(10) 0.0044(8) 0.0028(8) 0.0065(9) C19 0.0377(10) 0.0410(11) 0.0370(10) -0.0183(8) 0.0147(8) -0.0069(8) C20 0.0304(9) 0.0273(9) 0.0460(10) 0.0021(8) 0.0164(8) 0.0012(7) C21 0.0437(10) 0.0244(9) 0.0355(9) 0.0017(7) 0.0193(8) -0.0057(7) B1 0.0234(8) 0.0210(8) 0.0189(7) -0.0005(6) 0.0094(6) -0.0014(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C21 1.7790(18) . ? P1 C19 1.7852(18) . ? P1 C20 1.7889(18) . ? P1 C15 1.8060(17) . ? F1 C2 1.3578(19) . ? F2 C3 1.346(2) . ? F3 C4 1.342(2) . ? F4 C5 1.345(2) . ? F5 C6 1.3571(19) . ? F6 C8 1.362(2) . ? F7 C9 1.347(2) . ? F8 C10 1.349(2) . ? F9 C11 1.343(2) . ? F10 C12 1.348(2) . ? F11 C17 1.333(2) . ? F12 C17 1.335(2) . ? F13 C17 1.336(2) . ? F14 C18 1.325(2) . ? F15 C18 1.338(2) . ? F16 C18 1.336(3) . ? O1 C13 1.3810(19) . ? O1 B1 1.4913(19) . ? C1 C6 1.382(2) . ? C1 C2 1.392(2) . ? C1 B1 1.656(2) . ? C2 C3 1.383(2) . ? C3 C4 1.373(3) . ? C4 C5 1.373(3) . ? C5 C6 1.388(2) . ? C7 C8 1.383(2) . ? C7 C12 1.390(2) . ? C7 B1 1.664(2) . ? C8 C9 1.391(3) . ? C9 C10 1.366(3) . ? C10 C11 1.370(3) . ? C11 C12 1.383(3) . ? C13 C17 1.541(2) . ? C13 C18 1.542(3) . ? C13 C14 1.551(2) . ? C14 C15 1.536(2) . ? C15 C16 1.542(2) . ? C16 B1 1.620(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 C21 P1 C19 108.31(9) . . ? C21 P1 C20 109.78(9) . . ? C19 P1 C20 108.26(9) . . ? C21 P1 C15 107.77(8) . . ? C19 P1 C15 112.17(9) . . ? C20 P1 C15 110.52(8) . . ? C13 O1 B1 125.63(13) . . ? C6 C1 C2 113.23(14) . . ? C6 C1 B1 127.12(14) . . ? C2 C1 B1 119.63(14) . . ? F1 C2 C3 115.59(14) . . ? F1 C2 C1 119.58(14) . . ? C3 C2 C1 124.83(16) . . ? F2 C3 C4 119.99(15) . . ? F2 C3 C2 120.89(17) . . ? C4 C3 C2 119.12(16) . . ? F3 C4 C5 120.54(18) . . ? F3 C4 C3 120.58(17) . . ? C5 C4 C3 118.88(16) . . ? F4 C5 C4 119.69(16) . . ? F4 C5 C6 120.28(16) . . ? C4 C5 C6 120.03(17) . . ? F5 C6 C1 121.70(14) . . ? F5 C6 C5 114.38(15) . . ? C1 C6 C5 123.92(16) . . ? C8 C7 C12 113.38(15) . . ? C8 C7 B1 127.88(16) . . ? C12 C7 B1 118.72(14) . . ? F6 C8 C7 120.80(16) . . ? F6 C8 C9 115.11(17) . . ? C7 C8 C9 124.09(19) . . ? F7 C9 C10 120.37(19) . . ? F7 C9 C8 120.3(2) . . ? C10 C9 C8 119.31(19) . . ? F8 C10 C9 120.6(2) . . ? F8 C10 C11 119.7(2) . . ? C9 C10 C11 119.75(18) . . ? F9 C11 C10 120.15(18) . . ? F9 C11 C12 120.9(2) . . ? C10 C11 C12 118.9(2) . . ? F10 C12 C11 115.49(17) . . ? F10 C12 C7 120.00(14) . . ? C11 C12 C7 124.51(18) . . ? O1 C13 C17 104.38(14) . . ? O1 C13 C18 108.71(14) . . ? C17 C13 C18 109.51(15) . . ? O1 C13 C14 117.29(13) . . ? C17 C13 C14 107.33(14) . . ? C18 C13 C14 109.35(15) . . ? C15 C14 C13 111.78(13) . . ? C14 C15 C16 108.66(13) . . ? C14 C15 P1 112.07(11) . . ? C16 C15 P1 111.21(11) . . ? C15 C16 B1 109.64(13) . . ? F11 C17 F12 106.46(16) . . ? F11 C17 F13 107.02(16) . . ? F12 C17 F13 106.67(15) . . ? F11 C17 C13 110.10(14) . . ? F12 C17 C13 113.51(15) . . ? F13 C17 C13 112.68(16) . . ? F14 C18 F16 107.30(18) . . ? F14 C18 F15 106.69(17) . . ? F16 C18 F15 107.20(18) . . ? F14 C18 C13 112.79(17) . . ? F16 C18 C13 110.27(15) . . ? F15 C18 C13 112.28(17) . . ? O1 B1 C16 109.91(12) . . ? O1 B1 C1 107.95(13) . . ? C16 B1 C1 108.35(13) . . ? O1 B1 C7 108.03(13) . . ? C16 B1 C7 115.78(13) . . ? C1 B1 C7 106.53(12) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.71 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.429 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.055 #===end data_xz104_0m _database_code_depnum_ccdc_archive 'CCDC 870168' #TrackingRef '- all-CIFs.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H14 B F16 N O' _chemical_formula_weight 659.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1801(13) _cell_length_b 10.3330(14) _cell_length_c 13.984(2) _cell_angle_alpha 82.073(8) _cell_angle_beta 74.808(7) _cell_angle_gamma 80.634(8) _cell_volume 1256.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.742 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.188 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9652 _exptl_absorpt_correction_T_max 0.9870 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20411 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 27.61 _reflns_number_total 5755 _reflns_number_gt 3449 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0796P)^2^+1.6545P] 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 5755 _refine_ls_number_parameters 443 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1189 _refine_ls_R_factor_gt 0.0694 _refine_ls_wR_factor_ref 0.1995 _refine_ls_wR_factor_gt 0.1718 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.3767(3) 1.1595(2) 0.2740(2) 0.0317(6) Uani 1 1 d . . . B1 B 0.3464(4) 0.7890(3) 0.2250(3) 0.0267(7) Uani 1 1 d . A . O1 O 0.2414(2) 0.71518(19) 0.30849(15) 0.0272(5) Uani 1 1 d . A . F1 F 0.5936(2) 0.8557(2) 0.05965(14) 0.0398(5) Uani 1 1 d . . . F2 F 0.8871(2) 0.7530(2) 0.02593(16) 0.0513(6) Uani 1 1 d . . . F3 F 0.9849(2) 0.5653(2) 0.1583(2) 0.0685(8) Uani 1 1 d . . . F4 F 0.7836(3) 0.4830(3) 0.3268(2) 0.0786(9) Uani 1 1 d . . . F5 F 0.4946(2) 0.5875(2) 0.36619(17) 0.0566(6) Uani 1 1 d . . . F6 F 0.2073(3) 0.9915(2) 0.0797(2) 0.0632(7) Uani 1 1 d . . . F7 F 0.1569(4) 0.9401(3) -0.0883(2) 0.0956(11) Uani 1 1 d . . . F8 F 0.2105(3) 0.6891(4) -0.14030(19) 0.0881(10) Uani 1 1 d . . . F9 F 0.3176(3) 0.4895(3) -0.0163(2) 0.0721(8) Uani 1 1 d . . . F10 F 0.3763(3) 0.54043(19) 0.14911(17) 0.0494(6) Uani 1 1 d . . . F11 F -0.0527(11) 0.6481(7) 0.3816(8) 0.0485(19) Uani 0.474(14) 1 d P A 1 F11A F -0.0783(12) 0.7124(13) 0.3828(7) 0.069(3) Uani 0.526(14) 1 d P A 2 F12 F -0.0194(6) 0.8774(12) 0.2752(5) 0.061(3) Uani 0.474(14) 1 d P A 1 F12A F -0.0295(5) 0.7982(7) 0.2567(4) 0.0433(17) Uani 0.526(14) 1 d P A 2 F13 F -0.1405(6) 0.8534(6) 0.4012(5) 0.044(2) Uani 0.474(14) 1 d P A 1 F13A F -0.1066(8) 0.9068(11) 0.4290(5) 0.086(3) Uani 0.526(14) 1 d P A 2 F14 F 0.1178(3) 0.6266(3) 0.50051(17) 0.0741(9) Uani 1 1 d . . . F15 F 0.0373(4) 0.8170(3) 0.54420(19) 0.0873(10) Uani 1 1 d . . . F16 F 0.2741(4) 0.7615(6) 0.4921(2) 0.158(2) Uani 1 1 d . . . C1 C 0.5268(4) 0.7256(3) 0.2137(2) 0.0273(7) Uani 1 1 d . . . C2 C 0.6363(4) 0.7638(3) 0.1298(2) 0.0287(7) Uani 1 1 d . . . C3 C 0.7882(4) 0.7131(3) 0.1099(3) 0.0367(8) Uani 1 1 d . . . C4 C 0.8369(4) 0.6182(4) 0.1763(3) 0.0451(9) Uani 1 1 d . . . C5 C 0.7358(4) 0.5773(4) 0.2612(3) 0.0471(9) Uani 1 1 d . . . C6 C 0.5848(4) 0.6325(3) 0.2795(3) 0.0363(8) Uani 1 1 d . . . C7 C 0.3024(3) 0.7695(3) 0.1211(2) 0.0288(7) Uani 1 1 d . . . C8 C 0.2432(4) 0.8652(4) 0.0571(3) 0.0391(8) Uani 1 1 d . . . C9 C 0.2139(5) 0.8413(5) -0.0295(3) 0.0551(11) Uani 1 1 d . . . C10 C 0.2414(5) 0.7157(5) -0.0563(3) 0.0585(12) Uani 1 1 d . . . C11 C 0.2959(4) 0.6154(4) 0.0052(3) 0.0485(10) Uani 1 1 d . . . C12 C 0.3244(4) 0.6444(4) 0.0912(3) 0.0361(8) Uani 1 1 d . . . C13 C 0.1395(4) 0.7994(3) 0.3704(3) 0.0361(8) Uani 1 1 d . . . C14 C 0.2233(10) 0.9246(7) 0.3616(7) 0.045(2) Uani 0.50 1 d P A . H14A H 0.2903 0.9092 0.4104 0.054 Uiso 0.50 1 d P . . H14B H 0.1554 1.0026 0.3785 0.054 Uiso 0.50 1 d P . . C14A C 0.1565(7) 0.9450(6) 0.3252(5) 0.0221(13) Uani 0.50 1 d P A . H14C H 0.1467 1.0000 0.3791 0.027 Uiso 0.50 1 d P . . H14D H 0.0879 0.9801 0.2876 0.027 Uiso 0.50 1 d P . . C15 C 0.3144(5) 0.9350(4) 0.2660(3) 0.0509(11) Uani 1 1 d . . . H15B H 0.2285 0.9654 0.2380 0.061 Uiso 0.50 1 d P . . H15A H 0.3638 0.9117 0.3200 0.061 Uiso 0.50 1 d P . . C16 C 0.4012(4) 1.0439(3) 0.2144(3) 0.0392(8) Uani 1 1 d . A . H16A H 0.3716 1.0747 0.1510 0.047 Uiso 1 1 calc R . . H16B H 0.5110 1.0096 0.1978 0.047 Uiso 1 1 calc R . . C17 C -0.0231(14) 0.7728(12) 0.3497(10) 0.028(2) Uani 0.474(14) 1 d P A 1 C17A C -0.0141(14) 0.8213(15) 0.3670(8) 0.045(3) Uani 0.526(14) 1 d P A 2 C18 C 0.1419(5) 0.7505(5) 0.4769(3) 0.0523(11) Uani 1 1 d . A . C19 C 0.4667(4) 1.1609(3) 0.3371(3) 0.0428(9) Uani 1 1 d . . . C20 C 0.4363(5) 1.2606(4) 0.3980(3) 0.0556(11) Uani 1 1 d . . . H20A H 0.4974 1.2612 0.4432 0.067 Uiso 1 1 calc R . . C21 C 0.3179(5) 1.3591(4) 0.3938(3) 0.0583(12) Uani 1 1 d . . . H21A H 0.2952 1.4272 0.4367 0.070 Uiso 1 1 calc R . . C22 C 0.2339(5) 1.3582(4) 0.3278(4) 0.0561(12) Uani 1 1 d . . . H22A H 0.1538 1.4279 0.3233 0.067 Uiso 1 1 calc R . . C23 C 0.2617(4) 1.2587(3) 0.2670(3) 0.0450(9) Uani 1 1 d . . . C24 C 0.6010(5) 1.0575(5) 0.3384(5) 0.0769(16) Uani 1 1 d . . . H24A H 0.6060 0.9942 0.2911 0.115 Uiso 1 1 calc R . . H24B H 0.5903 1.0116 0.4055 0.115 Uiso 1 1 calc R . . H24C H 0.6944 1.0991 0.3193 0.115 Uiso 1 1 calc R . . C25 C 0.1717(7) 1.2615(5) 0.1919(5) 0.0882(19) Uani 1 1 d . . . H25A H 0.2071 1.1831 0.1556 0.132 Uiso 1 1 calc R . . H25B H 0.1851 1.3408 0.1450 0.132 Uiso 1 1 calc R . . H25C H 0.0636 1.2622 0.2258 0.132 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 N1 0.0359(15) 0.0228(13) 0.0352(15) -0.0049(11) -0.0033(12) -0.0075(11) B1 0.0314(18) 0.0191(16) 0.0276(18) -0.0044(14) -0.0035(14) -0.0023(14) O1 0.0335(12) 0.0202(10) 0.0251(11) -0.0060(8) -0.0004(9) -0.0031(9) F1 0.0358(10) 0.0469(12) 0.0332(11) 0.0086(9) -0.0079(8) -0.0073(9) F2 0.0325(11) 0.0672(15) 0.0452(13) -0.0009(11) 0.0041(9) -0.0072(10) F3 0.0309(12) 0.0597(16) 0.100(2) 0.0104(14) -0.0097(12) 0.0103(11) F4 0.0537(15) 0.0716(18) 0.096(2) 0.0456(16) -0.0265(14) 0.0007(13) F5 0.0440(12) 0.0631(15) 0.0508(14) 0.0262(11) -0.0076(10) -0.0066(11) F6 0.0832(18) 0.0345(12) 0.0877(19) 0.0159(12) -0.0565(15) -0.0141(12) F7 0.129(3) 0.104(2) 0.081(2) 0.0422(18) -0.079(2) -0.048(2) F8 0.092(2) 0.147(3) 0.0437(15) -0.0207(17) -0.0291(14) -0.038(2) F9 0.0685(17) 0.0875(19) 0.0717(17) -0.0570(15) -0.0161(14) -0.0039(14) F10 0.0622(14) 0.0326(11) 0.0585(14) -0.0186(10) -0.0243(11) 0.0062(10) F11 0.047(3) 0.029(3) 0.069(4) 0.001(4) -0.008(3) -0.018(3) F11A 0.068(6) 0.091(9) 0.062(4) -0.001(6) -0.019(4) -0.055(7) F12 0.037(3) 0.088(7) 0.052(3) 0.012(4) -0.013(2) -0.005(3) F12A 0.041(2) 0.048(4) 0.048(3) -0.003(2) -0.0196(19) -0.016(2) F13 0.025(3) 0.047(4) 0.053(4) -0.013(2) 0.000(2) 0.001(2) F13A 0.043(4) 0.126(7) 0.080(4) -0.045(4) -0.003(3) 0.022(4) F14 0.101(2) 0.0587(17) 0.0357(13) 0.0088(11) 0.0020(13) 0.0253(15) F15 0.114(2) 0.084(2) 0.0495(15) -0.0405(14) 0.0310(15) -0.0250(18) F16 0.075(2) 0.378(7) 0.0485(18) -0.064(3) -0.0155(16) -0.070(3) C1 0.0329(16) 0.0218(15) 0.0292(16) -0.0062(13) -0.0092(13) -0.0035(13) C2 0.0320(17) 0.0266(16) 0.0289(17) -0.0018(13) -0.0102(13) -0.0046(13) C3 0.0331(18) 0.0381(19) 0.0381(19) -0.0062(15) -0.0045(15) -0.0071(15) C4 0.0295(18) 0.039(2) 0.063(3) -0.0015(18) -0.0094(17) 0.0022(15) C5 0.045(2) 0.037(2) 0.059(3) 0.0104(18) -0.0226(19) -0.0002(17) C6 0.0362(18) 0.0325(18) 0.0387(19) 0.0043(15) -0.0089(15) -0.0070(15) C7 0.0213(14) 0.0354(17) 0.0271(16) -0.0039(13) -0.0019(12) -0.0023(13) C8 0.0364(18) 0.044(2) 0.040(2) 0.0050(16) -0.0137(16) -0.0131(16) C9 0.057(3) 0.072(3) 0.044(2) 0.017(2) -0.027(2) -0.027(2) C10 0.048(2) 0.106(4) 0.029(2) -0.009(2) -0.0133(18) -0.026(2) C11 0.039(2) 0.066(3) 0.044(2) -0.031(2) -0.0021(17) -0.0085(19) C12 0.0303(17) 0.044(2) 0.0331(18) -0.0117(16) -0.0048(14) -0.0009(15) C13 0.0384(19) 0.0217(16) 0.0398(19) -0.0063(14) 0.0069(15) -0.0044(14) C14 0.054(5) 0.024(4) 0.052(5) -0.018(4) 0.010(4) -0.015(4) C14A 0.023(3) 0.021(3) 0.024(3) -0.006(2) -0.011(3) 0.005(2) C15 0.060(2) 0.0282(18) 0.053(2) -0.0149(17) 0.0180(19) -0.0152(17) C16 0.047(2) 0.0324(18) 0.0393(19) -0.0122(15) -0.0030(16) -0.0133(16) C17 0.023(4) 0.022(6) 0.041(7) -0.011(4) -0.009(4) 0.003(4) C17A 0.044(6) 0.059(8) 0.026(5) -0.008(5) 0.003(4) -0.007(6) C18 0.046(2) 0.077(3) 0.035(2) -0.022(2) -0.0015(17) -0.010(2) C19 0.0392(19) 0.0331(19) 0.061(2) -0.0108(17) -0.0168(18) -0.0078(15) C20 0.062(3) 0.050(2) 0.065(3) -0.024(2) -0.018(2) -0.017(2) C21 0.059(3) 0.042(2) 0.067(3) -0.030(2) 0.015(2) -0.018(2) C22 0.048(2) 0.0227(18) 0.090(3) -0.010(2) -0.002(2) -0.0003(16) C23 0.052(2) 0.0229(17) 0.060(2) 0.0058(16) -0.0181(19) -0.0060(16) C24 0.058(3) 0.052(3) 0.141(5) -0.029(3) -0.057(3) 0.003(2) C25 0.119(5) 0.040(3) 0.127(5) 0.013(3) -0.085(4) 0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C23 1.360(5) . ? N1 C19 1.360(5) . ? N1 C16 1.504(4) . ? B1 O1 1.509(4) . ? B1 C15 1.642(5) . ? B1 C7 1.652(5) . ? B1 C1 1.654(5) . ? O1 C13 1.378(4) . ? F1 C2 1.357(4) . ? F2 C3 1.343(4) . ? F3 C4 1.351(4) . ? F4 C5 1.345(4) . ? F5 C6 1.347(4) . ? F6 C8 1.353(4) . ? F7 C9 1.346(5) . ? F8 C10 1.350(4) . ? F9 C11 1.347(5) . ? F10 C12 1.354(4) . ? F11 C17 1.351(12) . ? F11A C17A 1.320(12) . ? F12 C17 1.392(15) . ? F12A C17A 1.638(14) . ? F13 C17 1.357(13) . ? F13A C17A 1.355(13) . ? F14 C18 1.317(5) . ? F15 C18 1.331(5) . ? F16 C18 1.310(5) . ? C1 C6 1.379(5) . ? C1 C2 1.387(4) . ? C2 C3 1.377(5) . ? C3 C4 1.359(5) . ? C4 C5 1.364(6) . ? C5 C6 1.382(5) . ? C7 C12 1.381(5) . ? C7 C8 1.382(5) . ? C8 C9 1.368(5) . ? C9 C10 1.367(7) . ? C10 C11 1.369(6) . ? C11 C12 1.375(5) . ? C13 C17A 1.404(13) . ? C13 C18 1.510(6) . ? C13 C14A 1.565(7) . ? C13 C14 1.585(8) . ? C13 C17 1.665(13) . ? C14 C14A 0.879(10) . ? C14 C15 1.378(9) . ? C14A C15 1.463(7) . ? C15 C16 1.480(5) . ? C19 C20 1.374(5) . ? C19 C24 1.496(6) . ? C20 C21 1.370(6) . ? C21 C22 1.351(7) . ? C22 C23 1.373(6) . ? C23 C25 1.493(6) . ? 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 C23 N1 C19 120.9(3) . . ? C23 N1 C16 119.7(3) . . ? C19 N1 C16 119.4(3) . . ? O1 B1 C15 100.5(2) . . ? O1 B1 C7 106.5(2) . . ? C15 B1 C7 120.5(3) . . ? O1 B1 C1 111.8(2) . . ? C15 B1 C1 110.5(3) . . ? C7 B1 C1 106.9(2) . . ? C13 O1 B1 111.8(2) . . ? C6 C1 C2 113.5(3) . . ? C6 C1 B1 126.8(3) . . ? C2 C1 B1 119.8(3) . . ? F1 C2 C3 115.9(3) . . ? F1 C2 C1 119.1(3) . . ? C3 C2 C1 124.9(3) . . ? F2 C3 C4 119.9(3) . . ? F2 C3 C2 121.5(3) . . ? C4 C3 C2 118.6(3) . . ? F3 C4 C3 120.0(3) . . ? F3 C4 C5 120.3(3) . . ? C3 C4 C5 119.7(3) . . ? F4 C5 C4 119.8(3) . . ? F4 C5 C6 120.2(3) . . ? C4 C5 C6 120.0(3) . . ? F5 C6 C1 121.2(3) . . ? F5 C6 C5 115.6(3) . . ? C1 C6 C5 123.3(3) . . ? C12 C7 C8 113.2(3) . . ? C12 C7 B1 118.9(3) . . ? C8 C7 B1 127.9(3) . . ? F6 C8 C9 115.8(3) . . ? F6 C8 C7 119.9(3) . . ? C9 C8 C7 124.3(4) . . ? F7 C9 C10 119.4(4) . . ? F7 C9 C8 120.8(4) . . ? C10 C9 C8 119.8(4) . . ? F8 C10 C9 120.9(4) . . ? F8 C10 C11 120.1(5) . . ? C9 C10 C11 119.0(3) . . ? F9 C11 C10 120.7(4) . . ? F9 C11 C12 120.2(4) . . ? C10 C11 C12 119.1(4) . . ? F10 C12 C11 116.0(3) . . ? F10 C12 C7 119.4(3) . . ? C11 C12 C7 124.6(3) . . ? O1 C13 C17A 119.5(6) . . ? O1 C13 C18 108.7(3) . . ? C17A C13 C18 106.5(5) . . ? O1 C13 C14A 109.0(3) . . ? C17A C13 C14A 89.6(7) . . ? C18 C13 C14A 123.3(4) . . ? O1 C13 C14 104.8(4) . . ? C17A C13 C14 117.6(8) . . ? C18 C13 C14 97.3(4) . . ? C14A C13 C14 32.4(4) . . ? O1 C13 C17 100.1(5) . . ? C17A C13 C17 20.8(5) . . ? C18 C13 C17 109.1(5) . . ? C14A C13 C17 104.1(5) . . ? C14 C13 C17 135.3(6) . . ? C14A C14 C15 77.4(8) . . ? C14A C14 C13 72.6(7) . . ? C15 C14 C13 105.9(5) . . ? C14 C14A C15 66.8(7) . . ? C14 C14A C13 75.1(7) . . ? C15 C14A C13 102.8(4) . . ? C14 C15 C14A 35.9(4) . . ? C14 C15 C16 128.3(4) . . ? C14A C15 C16 127.7(4) . . ? C14 C15 B1 107.8(4) . . ? C14A C15 B1 104.3(3) . . ? C16 C15 B1 122.5(3) . . ? C15 C16 N1 113.9(3) . . ? F11 C17 F13 106.6(9) . . ? F11 C17 F12 147.9(14) . . ? F13 C17 F12 83.4(8) . . ? F11 C17 C13 111.8(8) . . ? F13 C17 C13 109.6(8) . . ? F12 C17 C13 92.2(9) . . ? F11A C17A F13A 107.0(10) . . ? F11A C17A C13 113.6(10) . . ? F13A C17A C13 116.0(9) . . ? F11A C17A F12A 76.0(9) . . ? F13A C17A F12A 126.6(10) . . ? C13 C17A F12A 110.2(8) . . ? F16 C18 F14 108.3(5) . . ? F16 C18 F15 106.3(4) . . ? F14 C18 F15 105.0(3) . . ? F16 C18 C13 109.8(4) . . ? F14 C18 C13 113.0(3) . . ? F15 C18 C13 114.1(4) . . ? N1 C19 C20 119.5(4) . . ? N1 C19 C24 120.6(3) . . ? C20 C19 C24 119.9(4) . . ? C21 C20 C19 120.2(4) . . ? C22 C21 C20 119.2(4) . . ? C21 C22 C23 121.5(4) . . ? N1 C23 C22 118.8(4) . . ? N1 C23 C25 120.3(4) . . ? C22 C23 C25 120.9(4) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.61 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.933 _refine_diff_density_min -0.988 _refine_diff_density_rms 0.067 #===end data_xz119_0m _database_code_depnum_ccdc_archive 'CCDC 870169' #TrackingRef '- all-CIFs.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H24 B F16 N O' _chemical_formula_weight 693.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.1705(5) _cell_length_b 16.0049(7) _cell_length_c 15.9286(8) _cell_angle_alpha 90.00 _cell_angle_beta 95.113(2) _cell_angle_gamma 90.00 _cell_volume 2836.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.623 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 _exptl_absorpt_coefficient_mu 0.170 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9619 _exptl_absorpt_correction_T_max 0.9733 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24942 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6445 _reflns_number_gt 4366 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0358P)^2^+1.1639P] 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 6445 _refine_ls_number_parameters 423 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0724 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.0947 _refine_ls_wR_factor_gt 0.0827 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _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 0.36490(9) 0.93344(7) 0.38962(7) 0.0329(3) Uani 1 1 d . . . F2 F 0.28852(11) 1.01955(7) 0.51546(7) 0.0385(3) Uani 1 1 d . . . F3 F 0.06522(11) 1.08779(7) 0.50369(7) 0.0389(3) Uani 1 1 d . . . F4 F -0.08358(10) 1.06509(7) 0.36030(7) 0.0360(3) Uani 1 1 d . . . F5 F -0.00705(9) 0.98280(7) 0.22982(7) 0.0312(3) Uani 1 1 d . . . F6 F 0.26673(10) 1.07928(6) 0.19193(7) 0.0324(3) Uani 1 1 d . . . F7 F 0.23588(12) 1.16411(7) 0.04792(7) 0.0420(3) Uani 1 1 d . . . F8 F 0.15633(11) 1.08818(7) -0.09788(7) 0.0373(3) Uani 1 1 d . . . F9 F 0.10290(11) 0.92056(7) -0.09598(7) 0.0372(3) Uani 1 1 d . . . F10 F 0.12623(11) 0.83516(6) 0.04347(7) 0.0353(3) Uani 1 1 d . . . F11 F 0.39953(10) 0.75989(8) 0.35057(7) 0.0396(3) Uani 1 1 d . . . F12 F 0.52094(10) 0.70106(7) 0.27141(8) 0.0423(3) Uani 1 1 d . . . F13 F 0.55458(10) 0.82667(7) 0.31652(8) 0.0397(3) Uani 1 1 d . . . F14 F 0.49591(11) 0.73384(7) 0.10664(8) 0.0439(3) Uani 1 1 d . . . F15 F 0.57357(10) 0.85018(8) 0.15077(8) 0.0460(3) Uani 1 1 d . . . F16 F 0.41103(11) 0.84955(8) 0.06845(7) 0.0402(3) Uani 1 1 d . . . O1 O 0.35943(10) 0.89015(7) 0.22632(8) 0.0216(3) Uani 1 1 d . . . N1 N 0.00399(13) 0.70199(9) 0.23855(9) 0.0199(3) Uani 1 1 d . . . C1 C 0.18474(15) 0.95589(10) 0.30001(11) 0.0199(4) Uani 1 1 d . . . C2 C 0.25338(16) 0.96646(11) 0.37660(12) 0.0235(4) Uani 1 1 d . . . C3 C 0.21575(17) 1.01048(11) 0.44388(11) 0.0258(4) Uani 1 1 d . . . C4 C 0.10351(18) 1.04552(11) 0.43797(11) 0.0259(4) Uani 1 1 d . . . C5 C 0.02928(16) 1.03517(11) 0.36522(12) 0.0251(4) Uani 1 1 d . . . C6 C 0.07120(16) 0.99165(11) 0.29934(11) 0.0220(4) Uani 1 1 d . . . C7 C 0.19301(15) 0.95207(11) 0.12890(11) 0.0201(4) Uani 1 1 d . . . C8 C 0.22098(16) 1.03654(11) 0.12219(11) 0.0226(4) Uani 1 1 d . . . C9 C 0.20823(17) 1.08222(11) 0.04880(12) 0.0267(4) Uani 1 1 d . . . C10 C 0.16778(17) 1.04422(11) -0.02581(12) 0.0251(4) Uani 1 1 d . . . C11 C 0.14033(16) 0.96065(12) -0.02444(11) 0.0248(4) Uani 1 1 d . . . C12 C 0.15277(16) 0.91801(11) 0.05111(11) 0.0229(4) Uani 1 1 d . . . C13 C 0.39265(15) 0.80816(11) 0.20925(12) 0.0234(4) Uani 1 1 d . . . C14 C 0.27844(15) 0.75450(11) 0.18869(12) 0.0237(4) Uani 1 1 d . . . H14A H 0.2590 0.7493 0.1271 0.028 Uiso 1 1 calc R . . H14B H 0.2884 0.6980 0.2136 0.028 Uiso 1 1 calc R . . C15 C 0.18080(15) 0.80407(11) 0.22946(11) 0.0206(4) Uani 1 1 d . . . H15A H 0.1939 0.7915 0.2911 0.025 Uiso 1 1 calc R . . C16 C 0.04909(15) 0.78518(11) 0.20530(12) 0.0217(4) Uani 1 1 d . . . H16A H 0.0352 0.7851 0.1430 0.026 Uiso 1 1 calc R . . H16B H 0.0003 0.8310 0.2265 0.026 Uiso 1 1 calc R . . C17 C 0.46782(17) 0.77417(12) 0.28714(13) 0.0303(4) Uani 1 1 d . . . C18 C 0.46933(17) 0.81027(12) 0.13438(13) 0.0302(4) Uani 1 1 d . . . C19 C -0.05243(16) 0.64280(11) 0.16743(12) 0.0249(4) Uani 1 1 d . . . C20 C -0.07984(18) 0.55938(12) 0.20882(13) 0.0314(5) Uani 1 1 d . . . H20A H -0.1229 0.5229 0.1659 0.038 Uiso 1 1 calc R . . H20B H -0.0029 0.5317 0.2278 0.038 Uiso 1 1 calc R . . C21 C -0.1546(2) 0.56680(13) 0.28342(13) 0.0389(5) Uani 1 1 d . . . H21A H -0.1658 0.5108 0.3080 0.047 Uiso 1 1 calc R . . H21B H -0.2348 0.5897 0.2645 0.047 Uiso 1 1 calc R . . C22 C -0.0918(2) 0.62408(13) 0.34963(13) 0.0375(5) Uani 1 1 d . . . H22A H -0.0144 0.5983 0.3709 0.045 Uiso 1 1 calc R . . H22B H -0.1420 0.6285 0.3976 0.045 Uiso 1 1 calc R . . C23 C -0.06730(17) 0.71210(12) 0.31775(13) 0.0289(4) Uani 1 1 d . . . C24 C 0.04359(19) 0.62851(13) 0.10652(13) 0.0338(5) Uani 1 1 d . . . H24A H 0.0190 0.5824 0.0684 0.051 Uiso 1 1 calc R . . H24B H 0.1200 0.6146 0.1385 0.051 Uiso 1 1 calc R . . H24C H 0.0533 0.6794 0.0736 0.051 Uiso 1 1 calc R . . C25 C -0.16337(17) 0.68146(13) 0.11924(13) 0.0346(5) Uani 1 1 d . . . H25A H -0.1814 0.6517 0.0659 0.052 Uiso 1 1 calc R . . H25B H -0.1477 0.7404 0.1078 0.052 Uiso 1 1 calc R . . H25C H -0.2321 0.6770 0.1532 0.052 Uiso 1 1 calc R . . C26 C 0.01316(19) 0.75845(14) 0.38440(13) 0.0357(5) Uani 1 1 d . . . H26A H -0.0257 0.7602 0.4372 0.054 Uiso 1 1 calc R . . H26B H 0.0265 0.8156 0.3651 0.054 Uiso 1 1 calc R . . H26C H 0.0905 0.7294 0.3938 0.054 Uiso 1 1 calc R . . C27 C -0.18324(18) 0.76180(15) 0.29848(15) 0.0432(6) Uani 1 1 d . . . H27A H -0.2152 0.7782 0.3514 0.065 Uiso 1 1 calc R . . H27B H -0.2425 0.7272 0.2654 0.065 Uiso 1 1 calc R . . H27C H -0.1664 0.8120 0.2662 0.065 Uiso 1 1 calc R . . B1 B 0.22612(17) 0.90144(12) 0.21970(13) 0.0202(4) Uani 1 1 d . . . HN1 H 0.0675(17) 0.6735(11) 0.2599(11) 0.018(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 0.0259(6) 0.0427(7) 0.0285(6) -0.0044(5) -0.0061(5) 0.0075(5) F2 0.0458(7) 0.0477(7) 0.0206(6) -0.0046(5) -0.0044(5) -0.0019(6) F3 0.0535(8) 0.0363(7) 0.0297(6) -0.0074(5) 0.0195(6) 0.0020(6) F4 0.0277(6) 0.0365(7) 0.0453(7) -0.0024(5) 0.0109(5) 0.0099(5) F5 0.0229(6) 0.0377(6) 0.0315(6) -0.0046(5) -0.0055(5) 0.0077(5) F6 0.0441(7) 0.0270(6) 0.0255(6) -0.0058(5) -0.0008(5) -0.0101(5) F7 0.0655(9) 0.0213(6) 0.0390(7) 0.0020(5) 0.0031(6) -0.0112(6) F8 0.0510(8) 0.0332(6) 0.0266(6) 0.0099(5) -0.0028(5) -0.0043(6) F9 0.0539(8) 0.0353(7) 0.0207(6) -0.0019(5) -0.0061(5) -0.0094(6) F10 0.0577(8) 0.0216(6) 0.0254(6) -0.0012(5) -0.0019(5) -0.0094(5) F11 0.0309(6) 0.0537(8) 0.0344(7) 0.0133(6) 0.0029(5) 0.0066(6) F12 0.0342(7) 0.0355(7) 0.0562(8) 0.0048(6) -0.0015(6) 0.0152(5) F13 0.0226(6) 0.0458(7) 0.0486(7) -0.0016(6) -0.0086(5) 0.0019(5) F14 0.0485(8) 0.0334(7) 0.0530(8) -0.0084(6) 0.0229(6) 0.0084(6) F15 0.0289(7) 0.0561(8) 0.0556(8) -0.0063(7) 0.0176(6) -0.0119(6) F16 0.0437(7) 0.0460(7) 0.0326(7) 0.0042(5) 0.0132(6) 0.0075(6) O1 0.0163(6) 0.0210(6) 0.0273(7) -0.0026(5) 0.0015(5) 0.0014(5) N1 0.0151(7) 0.0202(8) 0.0245(8) 0.0004(6) 0.0017(6) 0.0031(6) C1 0.0186(9) 0.0189(9) 0.0221(9) 0.0016(7) 0.0013(7) 0.0000(7) C2 0.0215(9) 0.0234(9) 0.0255(9) 0.0018(7) 0.0012(8) 0.0011(8) C3 0.0313(11) 0.0262(10) 0.0196(9) 0.0018(8) 0.0012(8) -0.0041(8) C4 0.0369(11) 0.0199(9) 0.0232(9) -0.0027(7) 0.0144(8) -0.0034(8) C5 0.0222(10) 0.0204(9) 0.0340(11) 0.0027(8) 0.0098(8) 0.0035(7) C6 0.0229(9) 0.0204(9) 0.0223(9) 0.0001(7) 0.0000(8) -0.0004(7) C7 0.0148(8) 0.0229(9) 0.0226(9) -0.0014(7) 0.0015(7) 0.0019(7) C8 0.0208(9) 0.0234(9) 0.0232(9) -0.0044(7) 0.0000(8) 0.0001(7) C9 0.0297(10) 0.0185(9) 0.0320(10) 0.0009(8) 0.0037(8) -0.0024(8) C10 0.0251(10) 0.0258(10) 0.0243(10) 0.0061(8) 0.0005(8) 0.0017(8) C11 0.0242(10) 0.0290(10) 0.0206(9) -0.0034(8) -0.0017(8) -0.0022(8) C12 0.0239(10) 0.0188(9) 0.0256(9) -0.0005(7) 0.0006(8) -0.0025(7) C13 0.0183(9) 0.0216(9) 0.0306(10) -0.0003(8) 0.0047(8) 0.0029(7) C14 0.0213(9) 0.0207(9) 0.0292(10) 0.0003(8) 0.0027(8) 0.0001(7) C15 0.0169(9) 0.0220(9) 0.0229(9) 0.0014(7) 0.0017(7) 0.0018(7) C16 0.0186(9) 0.0197(9) 0.0268(10) 0.0021(7) 0.0021(7) -0.0018(7) C17 0.0205(10) 0.0315(11) 0.0392(12) 0.0021(9) 0.0041(9) 0.0064(8) C18 0.0273(10) 0.0268(10) 0.0375(11) -0.0038(9) 0.0079(9) 0.0032(8) C19 0.0245(10) 0.0235(10) 0.0261(10) -0.0023(8) -0.0020(8) -0.0035(8) C20 0.0330(11) 0.0241(10) 0.0360(11) -0.0002(8) -0.0025(9) -0.0052(8) C21 0.0381(12) 0.0353(12) 0.0434(13) 0.0073(10) 0.0046(10) -0.0119(10) C22 0.0360(12) 0.0433(13) 0.0348(12) 0.0046(10) 0.0108(9) -0.0087(10) C23 0.0228(10) 0.0336(11) 0.0320(11) -0.0041(9) 0.0108(8) -0.0025(8) C24 0.0385(12) 0.0314(11) 0.0317(11) -0.0089(9) 0.0045(9) -0.0018(9) C25 0.0276(11) 0.0329(11) 0.0410(12) 0.0029(9) -0.0098(9) -0.0057(9) C26 0.0375(12) 0.0418(12) 0.0294(11) -0.0052(9) 0.0124(9) -0.0043(10) C27 0.0240(11) 0.0475(14) 0.0598(15) -0.0066(12) 0.0134(10) 0.0040(10) B1 0.0168(10) 0.0219(10) 0.0214(10) -0.0019(8) 0.0000(8) 0.0009(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 F1 C2 1.352(2) . ? F2 C3 1.348(2) . ? F3 C4 1.348(2) . ? F4 C5 1.344(2) . ? F5 C6 1.356(2) . ? F6 C8 1.364(2) . ? F7 C9 1.347(2) . ? F8 C10 1.343(2) . ? F9 C11 1.342(2) . ? F10 C12 1.362(2) . ? F11 C17 1.339(2) . ? F12 C17 1.346(2) . ? F13 C17 1.335(2) . ? F14 C18 1.343(2) . ? F15 C18 1.333(2) . ? F16 C18 1.342(2) . ? O1 C13 1.397(2) . ? O1 B1 1.494(2) . ? N1 C16 1.535(2) . ? N1 C23 1.559(2) . ? N1 C19 1.565(2) . ? C1 C6 1.391(2) . ? C1 C2 1.392(2) . ? C1 B1 1.648(3) . ? C2 C3 1.379(3) . ? C3 C4 1.369(3) . ? C4 C5 1.373(3) . ? C5 C6 1.376(3) . ? C7 C12 1.391(2) . ? C7 C8 1.394(2) . ? C7 B1 1.670(3) . ? C8 C9 1.376(3) . ? C9 C10 1.375(3) . ? C10 C11 1.373(3) . ? C11 C12 1.380(3) . ? C13 C18 1.529(3) . ? C13 C17 1.534(3) . ? C13 C14 1.549(2) . ? C14 C15 1.539(2) . ? C15 C16 1.518(2) . ? C15 B1 1.650(3) . ? C19 C24 1.526(3) . ? C19 C25 1.529(3) . ? C19 C20 1.532(3) . ? C20 C21 1.517(3) . ? C21 C22 1.521(3) . ? C22 C23 1.530(3) . ? C23 C26 1.522(3) . ? C23 C27 1.528(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O1 B1 112.34(13) . . ? C16 N1 C23 113.34(14) . . ? C16 N1 C19 113.50(13) . . ? C23 N1 C19 116.53(13) . . ? C6 C1 C2 112.79(16) . . ? C6 C1 B1 122.04(15) . . ? C2 C1 B1 125.03(15) . . ? F1 C2 C3 114.89(15) . . ? F1 C2 C1 120.99(16) . . ? C3 C2 C1 124.12(17) . . ? F2 C3 C4 119.58(17) . . ? F2 C3 C2 120.65(17) . . ? C4 C3 C2 119.77(16) . . ? F3 C4 C3 120.29(17) . . ? F3 C4 C5 120.42(17) . . ? C3 C4 C5 119.27(17) . . ? F4 C5 C4 119.92(17) . . ? F4 C5 C6 121.13(17) . . ? C4 C5 C6 118.92(17) . . ? F5 C6 C5 115.94(16) . . ? F5 C6 C1 118.98(15) . . ? C5 C6 C1 125.07(16) . . ? C12 C7 C8 111.64(16) . . ? C12 C7 B1 127.61(16) . . ? C8 C7 B1 120.20(15) . . ? F6 C8 C9 115.36(15) . . ? F6 C8 C7 119.62(16) . . ? C9 C8 C7 125.01(16) . . ? F7 C9 C10 118.65(16) . . ? F7 C9 C8 121.31(16) . . ? C10 C9 C8 120.04(16) . . ? F8 C10 C11 121.31(16) . . ? F8 C10 C9 120.40(16) . . ? C11 C10 C9 118.29(16) . . ? F9 C11 C10 120.37(16) . . ? F9 C11 C12 120.26(16) . . ? C10 C11 C12 119.37(16) . . ? F10 C12 C11 113.55(15) . . ? F10 C12 C7 120.77(15) . . ? C11 C12 C7 125.63(16) . . ? O1 C13 C18 107.93(15) . . ? O1 C13 C17 108.14(15) . . ? C18 C13 C17 109.53(15) . . ? O1 C13 C14 109.51(14) . . ? C18 C13 C14 110.81(15) . . ? C17 C13 C14 110.83(15) . . ? C15 C14 C13 103.08(14) . . ? C16 C15 C14 119.86(15) . . ? C16 C15 B1 117.57(14) . . ? C14 C15 B1 102.26(14) . . ? C15 C16 N1 115.21(14) . . ? F13 C17 F11 106.71(16) . . ? F13 C17 F12 107.10(15) . . ? F11 C17 F12 106.41(16) . . ? F13 C17 C13 112.83(16) . . ? F11 C17 C13 111.29(15) . . ? F12 C17 C13 112.10(16) . . ? F15 C18 F16 106.46(16) . . ? F15 C18 F14 106.61(15) . . ? F16 C18 F14 105.98(16) . . ? F15 C18 C13 113.44(16) . . ? F16 C18 C13 110.75(15) . . ? F14 C18 C13 113.08(16) . . ? C24 C19 C25 109.00(16) . . ? C24 C19 C20 108.76(16) . . ? C25 C19 C20 112.61(16) . . ? C24 C19 N1 106.87(14) . . ? C25 C19 N1 111.99(15) . . ? C20 C19 N1 107.40(14) . . ? C21 C20 C19 114.46(17) . . ? C20 C21 C22 109.77(17) . . ? C21 C22 C23 114.20(17) . . ? C26 C23 C27 108.89(17) . . ? C26 C23 C22 109.23(17) . . ? C27 C23 C22 111.87(17) . . ? C26 C23 N1 107.62(15) . . ? C27 C23 N1 112.11(16) . . ? C22 C23 N1 106.99(15) . . ? O1 B1 C1 110.85(14) . . ? O1 B1 C15 101.03(13) . . ? C1 B1 C15 108.47(14) . . ? O1 B1 C7 105.19(14) . . ? C1 B1 C7 111.10(14) . . ? C15 B1 C7 119.57(14) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.297 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.049 #===end data_xz106_0m _database_code_depnum_ccdc_archive 'CCDC 870170' #TrackingRef '- all-CIFs.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25.50 H17 B Cl F16 N O' _chemical_formula_weight 703.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.9380(9) _cell_length_b 15.0103(12) _cell_length_c 16.2877(13) _cell_angle_alpha 108.689(4) _cell_angle_beta 100.946(4) _cell_angle_gamma 90.150(4) _cell_volume 2708.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.726 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1404 _exptl_absorpt_coefficient_mu 0.275 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9495 _exptl_absorpt_correction_T_max 0.9783 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 45506 _diffrn_reflns_av_R_equivalents 0.0634 _diffrn_reflns_av_sigmaI/netI 0.0991 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 27.84 _reflns_number_total 12425 _reflns_number_gt 5780 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1484P)^2^+0.8921P] 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 12425 _refine_ls_number_parameters 826 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1814 _refine_ls_R_factor_gt 0.0839 _refine_ls_wR_factor_ref 0.2899 _refine_ls_wR_factor_gt 0.2375 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 Cl1 Cl 0.57391(16) 0.67725(13) 0.03986(12) 0.0689(5) Uani 1 1 d . . . Cl2 Cl 0.55180(16) 0.82696(13) -0.03828(13) 0.0740(6) Uani 1 1 d . . . F1 F 0.0029(3) -0.0705(2) 0.7206(2) 0.0525(9) Uani 1 1 d . . . F2 F -0.0808(3) -0.2319(3) 0.5968(2) 0.0615(10) Uani 1 1 d . . . F3 F 0.0635(3) -0.3574(2) 0.5183(2) 0.0625(10) Uani 1 1 d . . . F4 F 0.2926(3) -0.3122(2) 0.5637(2) 0.0530(9) Uani 1 1 d . . . F5 F 0.3775(2) -0.1500(2) 0.6840(2) 0.0429(8) Uani 1 1 d . . . F6 F 0.3321(3) -0.0994(2) 0.8884(2) 0.0488(8) Uani 1 1 d . . . F7 F 0.3008(4) -0.0913(3) 1.0478(2) 0.0743(12) Uani 1 1 d . . . F8 F 0.1524(4) 0.0277(3) 1.1262(2) 0.0772(13) Uani 1 1 d . . . F9 F 0.0337(3) 0.1362(3) 1.0399(2) 0.0651(11) Uani 1 1 d . . . F10 F 0.0599(3) 0.1275(2) 0.8815(2) 0.0535(9) Uani 1 1 d . . . F11 F 0.1888(3) 0.0072(3) 0.5672(2) 0.0614(10) Uani 1 1 d . . . F12 F 0.0301(3) 0.0652(3) 0.5908(2) 0.0756(13) Uani 1 1 d . . . F13 F 0.1518(4) 0.1398(4) 0.5528(3) 0.0871(14) Uani 1 1 d . . . F14 F 0.0321(3) 0.2205(3) 0.7281(3) 0.0640(10) Uani 1 1 d . . . F15 F 0.1681(3) 0.2907(3) 0.6996(3) 0.0749(12) Uani 1 1 d . . . F16 F 0.1862(3) 0.2667(2) 0.8229(2) 0.0591(10) Uani 1 1 d . . . F17 F 0.8513(2) 0.4312(2) 0.7327(2) 0.0445(8) Uani 1 1 d . . . F18 F 0.8669(3) 0.2711(3) 0.6063(2) 0.0559(9) Uani 1 1 d . . . F19 F 0.6785(3) 0.1512(2) 0.5214(2) 0.0614(10) Uani 1 1 d . . . F20 F 0.4728(3) 0.1979(2) 0.5656(2) 0.0596(10) Uani 1 1 d . . . F21 F 0.4538(2) 0.3572(2) 0.6894(2) 0.0439(8) Uani 1 1 d . . . F22 F 0.8786(2) 0.6316(2) 0.8886(2) 0.0480(8) Uani 1 1 d . . . F23 F 0.9896(3) 0.6362(2) 1.0455(2) 0.0569(10) Uani 1 1 d . . . F24 F 0.9142(3) 0.5267(3) 1.1312(2) 0.0660(11) Uani 1 1 d . . . F25 F 0.7226(3) 0.4101(3) 1.0533(2) 0.0656(11) Uani 1 1 d . . . F26 F 0.6059(3) 0.4055(2) 0.8955(2) 0.0459(8) Uani 1 1 d . . . F27 F 0.5936(3) 0.5041(3) 0.5740(2) 0.0582(10) Uani 1 1 d . . . F28 F 0.7633(3) 0.5659(3) 0.5981(2) 0.0732(12) Uani 1 1 d . . . F29 F 0.6217(3) 0.6371(3) 0.5560(2) 0.0757(12) Uani 1 1 d . . . F30 F 0.8281(3) 0.7241(3) 0.7324(3) 0.0675(11) Uani 1 1 d . . . F31 F 0.6752(3) 0.7914(3) 0.6995(3) 0.0791(13) Uani 1 1 d . . . F32 F 0.7209(3) 0.7710(2) 0.8258(3) 0.0601(10) Uani 1 1 d . . . O1 O 0.1632(3) 0.0777(2) 0.7467(2) 0.0342(8) Uani 1 1 d . . . O2 O 0.7058(3) 0.5818(2) 0.7541(2) 0.0319(8) Uani 1 1 d . . . N1 N 0.7123(4) 0.0790(3) 0.7317(3) 0.0510(14) Uani 1 1 d . . . N2 N 0.1468(3) 0.5743(3) 0.7270(3) 0.0433(12) Uani 1 1 d . . . C1 C 0.1941(4) -0.0979(4) 0.7075(3) 0.0316(11) Uani 1 1 d . . . C2 C 0.0779(4) -0.1266(4) 0.6821(4) 0.0371(13) Uani 1 1 d . . . C3 C 0.0326(5) -0.2108(4) 0.6185(4) 0.0426(14) Uani 1 1 d . . . C4 C 0.1050(5) -0.2740(4) 0.5794(4) 0.0432(14) Uani 1 1 d . . . C5 C 0.2204(5) -0.2511(4) 0.6031(4) 0.0410(13) Uani 1 1 d . . . C6 C 0.2620(4) -0.1653(4) 0.6660(3) 0.0321(12) Uani 1 1 d . . . C7 C 0.2011(4) 0.0145(4) 0.8762(3) 0.0323(12) Uani 1 1 d . . . C8 C 0.2571(5) -0.0381(4) 0.9237(4) 0.0389(13) Uani 1 1 d . . . C9 C 0.2419(5) -0.0360(4) 1.0066(4) 0.0496(16) Uani 1 1 d . . . C10 C 0.1681(5) 0.0230(5) 1.0457(4) 0.0502(16) Uani 1 1 d . . . C11 C 0.1086(5) 0.0775(4) 1.0030(4) 0.0446(15) Uani 1 1 d . . . C12 C 0.1255(4) 0.0722(4) 0.9196(4) 0.0415(14) Uani 1 1 d . . . C13 C 0.1969(4) 0.1333(4) 0.7009(4) 0.0363(12) Uani 1 1 d . . . C14 C 0.3269(4) 0.1537(4) 0.7126(4) 0.0358(12) Uani 1 1 d . . . H14A H 0.3417 0.1710 0.6617 0.043 Uiso 1 1 calc R . . H14B H 0.3534 0.2083 0.7668 0.043 Uiso 1 1 calc R . . C15 C 0.3959(4) 0.0695(3) 0.7195(3) 0.0312(11) Uani 1 1 d . . . H15A H 0.3728 0.0156 0.6631 0.037 Uiso 1 1 calc R . . C16 C 0.3696(4) 0.0400(3) 0.7961(3) 0.0308(11) Uani 1 1 d . . . H16A H 0.3922 0.0930 0.8522 0.037 Uiso 1 1 calc R . . H16B H 0.4147 -0.0139 0.8013 0.037 Uiso 1 1 calc R . . C17 C 0.1417(5) 0.0861(5) 0.6027(4) 0.0504(16) Uani 1 1 d . . . C18 C 0.1449(5) 0.2283(4) 0.7360(4) 0.0473(15) Uani 1 1 d . . . C19 C 0.6000(5) 0.0242(5) 0.6962(5) 0.063(2) Uani 1 1 d . . . H19A H 0.6014 -0.0241 0.7267 0.076 Uiso 1 1 calc R . . C20 C 0.5208(4) 0.0944(3) 0.7344(3) 0.0295(11) Uani 1 1 d . . . C21 C 0.5830(4) 0.1722(4) 0.7878(3) 0.0321(11) Uani 1 1 d . . . H21A H 0.5532 0.2268 0.8228 0.038 Uiso 1 1 calc R . . C22 C 0.7023(4) 0.1617(4) 0.7847(3) 0.0322(12) Uani 1 1 d . . . C23 C 0.8170(5) 0.0372(6) 0.7051(6) 0.096(3) Uani 1 1 d . . . H23A H 0.8834 0.0659 0.7524 0.145 Uiso 1 1 calc R . . H23B H 0.8266 0.0487 0.6508 0.145 Uiso 1 1 calc R . . H23C H 0.8106 -0.0309 0.6943 0.145 Uiso 1 1 calc R . . C24 C 0.5796(6) -0.0264(6) 0.6051(5) 0.084(3) Uani 1 1 d . . . H24A H 0.5074 -0.0651 0.5882 0.125 Uiso 1 1 calc R . . H24B H 0.6423 -0.0672 0.5919 0.125 Uiso 1 1 calc R . . H24C H 0.5748 0.0179 0.5717 0.125 Uiso 1 1 calc R . . C25 C 0.8004(4) 0.2299(4) 0.8361(4) 0.0414(13) Uani 1 1 d . . . H25A H 0.8513 0.2025 0.8749 0.062 Uiso 1 1 calc R . . H25B H 0.7724 0.2879 0.8719 0.062 Uiso 1 1 calc R . . H25C H 0.8426 0.2445 0.7954 0.062 Uiso 1 1 calc R . . C26 C 0.6515(4) 0.4060(3) 0.7162(3) 0.0284(11) Uani 1 1 d . . . C27 C 0.7537(4) 0.3758(4) 0.6912(3) 0.0335(12) Uani 1 1 d . . . C28 C 0.7651(5) 0.2933(4) 0.6279(4) 0.0391(13) Uani 1 1 d . . . C29 C 0.6694(5) 0.2331(4) 0.5850(4) 0.0444(14) Uani 1 1 d . . . C30 C 0.5668(5) 0.2571(4) 0.6070(4) 0.0409(13) Uani 1 1 d . . . C31 C 0.5604(4) 0.3414(4) 0.6723(3) 0.0340(12) Uani 1 1 d . . . C32 C 0.7330(4) 0.5191(3) 0.8838(3) 0.0279(11) Uani 1 1 d . . . C33 C 0.8331(4) 0.5757(3) 0.9263(3) 0.0323(11) Uani 1 1 d . . . C34 C 0.8943(4) 0.5791(4) 1.0086(4) 0.0397(13) Uani 1 1 d . . . C35 C 0.8562(5) 0.5243(4) 1.0515(4) 0.0450(15) Uani 1 1 d . . . C36 C 0.7594(5) 0.4658(4) 1.0122(4) 0.0428(14) Uani 1 1 d . . . C37 C 0.7007(4) 0.4661(3) 0.9308(3) 0.0319(11) Uani 1 1 d . . . C38 C 0.6496(4) 0.6345(4) 0.7052(4) 0.0371(13) Uani 1 1 d . . . C39 C 0.5243(4) 0.6535(4) 0.7131(4) 0.0369(12) Uani 1 1 d . . . H39A H 0.5235 0.7099 0.7652 0.044 Uiso 1 1 calc R . . H39B H 0.4844 0.6674 0.6599 0.044 Uiso 1 1 calc R . . C40 C 0.4593(4) 0.5705(4) 0.7224(3) 0.0302(11) Uani 1 1 d . . . H40A H 0.4554 0.5149 0.6677 0.036 Uiso 1 1 calc R . . C41 C 0.5239(4) 0.5451(3) 0.8020(3) 0.0290(11) Uani 1 1 d . . . H41A H 0.4809 0.4927 0.8093 0.035 Uiso 1 1 calc R . . H41B H 0.5301 0.6002 0.8565 0.035 Uiso 1 1 calc R . . C42 C 0.6572(5) 0.5862(5) 0.6082(4) 0.0544(17) Uani 1 1 d . . . C43 C 0.7196(5) 0.7299(5) 0.7403(5) 0.0511(16) Uani 1 1 d . . . C44 C 0.2415(5) 0.5220(4) 0.6956(4) 0.0541(17) Uani 1 1 d . . . H44A H 0.2557 0.4745 0.7271 0.065 Uiso 1 1 calc R . . C45 C 0.3406(4) 0.5937(4) 0.7334(3) 0.0291(11) Uani 1 1 d . . . C46 C 0.3027(4) 0.6703(4) 0.7842(3) 0.0334(12) Uani 1 1 d . . . H46A H 0.3490 0.7260 0.8193 0.040 Uiso 1 1 calc R . . C47 C 0.1824(4) 0.6577(4) 0.7790(3) 0.0303(11) Uani 1 1 d . . . C48 C 0.0292(5) 0.5300(5) 0.7017(5) 0.075(2) Uani 1 1 d . . . H48A H -0.0106 0.5551 0.7508 0.112 Uiso 1 1 calc R . . H48B H 0.0321 0.4616 0.6878 0.112 Uiso 1 1 calc R . . H48C H -0.0119 0.5439 0.6495 0.112 Uiso 1 1 calc R . . C49 C 0.2196(5) 0.4690(5) 0.6013(4) 0.066(2) Uani 1 1 d . . . H49A H 0.1501 0.4273 0.5857 0.100 Uiso 1 1 calc R . . H49B H 0.2845 0.4312 0.5874 0.100 Uiso 1 1 calc R . . H49C H 0.2094 0.5129 0.5675 0.100 Uiso 1 1 calc R . . C50 C 0.1088(5) 0.7258(4) 0.8285(4) 0.0448(14) Uani 1 1 d . . . H50A H 0.0501 0.7433 0.7866 0.067 Uiso 1 1 calc R . . H50B H 0.1559 0.7823 0.8682 0.067 Uiso 1 1 calc R . . H50C H 0.0720 0.6967 0.8634 0.067 Uiso 1 1 calc R . . C51 C 0.6458(6) 0.7530(5) 0.0005(5) 0.0619(18) Uani 1 1 d . . . H51A H 0.7070 0.7920 0.0488 0.074 Uiso 1 1 calc R . . H51B H 0.6820 0.7149 -0.0480 0.074 Uiso 1 1 calc R . . B1 B 0.2348(5) 0.0104(4) 0.7798(4) 0.0322(13) Uani 1 1 d . . . B2 B 0.6505(5) 0.5145(4) 0.7879(4) 0.0295(13) 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 Cl1 0.0706(12) 0.0640(11) 0.0656(11) 0.0061(9) 0.0247(9) -0.0101(9) Cl2 0.0665(12) 0.0643(11) 0.0736(12) 0.0084(10) -0.0034(9) 0.0086(9) F1 0.0255(17) 0.065(2) 0.063(2) 0.0147(18) 0.0093(15) -0.0029(15) F2 0.040(2) 0.076(3) 0.063(2) 0.023(2) -0.0034(17) -0.0250(18) F3 0.078(3) 0.0416(19) 0.052(2) 0.0065(17) -0.0110(18) -0.0171(18) F4 0.071(2) 0.0391(18) 0.0416(19) 0.0050(15) 0.0087(17) 0.0139(17) F5 0.0306(17) 0.0438(18) 0.0503(19) 0.0100(15) 0.0081(14) 0.0080(13) F6 0.050(2) 0.051(2) 0.052(2) 0.0247(17) 0.0119(16) 0.0118(16) F7 0.084(3) 0.096(3) 0.058(2) 0.050(2) 0.006(2) 0.003(2) F8 0.089(3) 0.098(3) 0.044(2) 0.015(2) 0.028(2) -0.027(2) F9 0.054(2) 0.061(2) 0.069(2) -0.0075(19) 0.0363(19) -0.0067(18) F10 0.0387(18) 0.056(2) 0.070(2) 0.0185(19) 0.0245(17) 0.0161(16) F11 0.043(2) 0.086(3) 0.0381(19) 0.0010(19) 0.0014(16) 0.0149(19) F12 0.0289(19) 0.124(4) 0.054(2) 0.008(2) -0.0030(16) 0.008(2) F13 0.086(3) 0.130(4) 0.062(3) 0.059(3) 0.005(2) 0.021(3) F14 0.0310(19) 0.078(3) 0.087(3) 0.033(2) 0.0124(18) 0.0259(17) F15 0.073(3) 0.062(2) 0.119(3) 0.060(3) 0.034(2) 0.032(2) F16 0.046(2) 0.048(2) 0.071(3) 0.0043(19) 0.0095(18) 0.0197(16) F17 0.0221(15) 0.060(2) 0.0448(18) 0.0107(16) 0.0034(13) 0.0041(14) F18 0.048(2) 0.073(2) 0.046(2) 0.0137(18) 0.0194(16) 0.0200(18) F19 0.077(3) 0.048(2) 0.053(2) -0.0013(18) 0.0315(19) 0.0029(18) F20 0.056(2) 0.052(2) 0.055(2) -0.0091(17) 0.0181(17) -0.0207(17) F21 0.0309(17) 0.0379(17) 0.055(2) 0.0038(15) 0.0109(14) -0.0103(13) F22 0.0272(16) 0.058(2) 0.058(2) 0.0257(17) -0.0049(14) -0.0145(14) F23 0.0316(18) 0.063(2) 0.053(2) -0.0008(18) -0.0120(15) -0.0021(16) F24 0.066(2) 0.089(3) 0.0342(19) 0.0169(19) -0.0064(17) 0.020(2) F25 0.069(2) 0.088(3) 0.059(2) 0.053(2) 0.0084(19) 0.006(2) F26 0.0427(18) 0.0469(19) 0.052(2) 0.0256(16) 0.0032(15) -0.0084(15) F27 0.0377(19) 0.094(3) 0.0382(19) 0.0165(19) 0.0049(15) -0.0001(19) F28 0.0292(19) 0.146(4) 0.052(2) 0.039(2) 0.0150(16) 0.012(2) F29 0.061(2) 0.128(4) 0.062(2) 0.063(3) 0.0140(19) 0.010(2) F30 0.0267(18) 0.091(3) 0.100(3) 0.053(2) 0.0110(18) -0.0134(18) F31 0.053(2) 0.076(3) 0.132(4) 0.073(3) 0.008(2) -0.008(2) F32 0.047(2) 0.049(2) 0.081(3) 0.020(2) 0.0080(19) -0.0137(16) O1 0.0227(17) 0.040(2) 0.044(2) 0.0190(17) 0.0071(15) 0.0062(15) O2 0.0182(16) 0.042(2) 0.041(2) 0.0235(17) 0.0025(14) -0.0007(14) N1 0.019(2) 0.050(3) 0.062(3) -0.010(3) 0.006(2) 0.000(2) N2 0.017(2) 0.053(3) 0.052(3) 0.006(2) 0.007(2) -0.005(2) C1 0.028(3) 0.036(3) 0.031(3) 0.014(2) 0.004(2) 0.001(2) C2 0.028(3) 0.046(3) 0.040(3) 0.016(3) 0.011(2) 0.002(2) C3 0.036(3) 0.053(4) 0.039(3) 0.023(3) -0.006(3) -0.018(3) C4 0.055(4) 0.038(3) 0.033(3) 0.013(3) -0.002(3) -0.009(3) C5 0.051(4) 0.041(3) 0.034(3) 0.017(3) 0.007(3) 0.009(3) C6 0.030(3) 0.032(3) 0.034(3) 0.012(2) 0.004(2) 0.002(2) C7 0.023(3) 0.037(3) 0.034(3) 0.008(2) 0.003(2) -0.007(2) C8 0.034(3) 0.039(3) 0.044(3) 0.013(3) 0.008(3) -0.005(2) C9 0.055(4) 0.051(4) 0.042(4) 0.018(3) 0.003(3) -0.016(3) C10 0.052(4) 0.056(4) 0.033(3) 0.000(3) 0.013(3) -0.022(3) C11 0.036(3) 0.044(3) 0.043(3) -0.004(3) 0.015(3) -0.013(3) C12 0.029(3) 0.039(3) 0.054(4) 0.012(3) 0.007(3) -0.007(2) C13 0.025(3) 0.047(3) 0.041(3) 0.020(3) 0.005(2) 0.010(2) C14 0.026(3) 0.037(3) 0.048(3) 0.019(3) 0.007(2) 0.009(2) C15 0.020(2) 0.033(3) 0.040(3) 0.011(2) 0.005(2) 0.001(2) C16 0.023(2) 0.030(3) 0.039(3) 0.011(2) 0.005(2) 0.001(2) C17 0.034(3) 0.073(4) 0.048(4) 0.027(3) 0.004(3) 0.018(3) C18 0.038(3) 0.049(4) 0.058(4) 0.023(3) 0.009(3) 0.015(3) C19 0.019(3) 0.061(4) 0.080(5) -0.015(4) 0.007(3) -0.001(3) C20 0.025(3) 0.031(3) 0.033(3) 0.012(2) 0.005(2) 0.006(2) C21 0.023(3) 0.033(3) 0.041(3) 0.010(2) 0.012(2) 0.005(2) C22 0.028(3) 0.037(3) 0.031(3) 0.011(2) 0.004(2) 0.003(2) C23 0.019(3) 0.100(6) 0.124(7) -0.029(5) 0.018(4) 0.006(4) C24 0.037(4) 0.092(6) 0.081(6) -0.030(5) 0.017(4) -0.016(4) C25 0.031(3) 0.040(3) 0.047(3) 0.009(3) 0.001(2) -0.001(2) C26 0.026(3) 0.035(3) 0.028(3) 0.015(2) 0.006(2) 0.001(2) C27 0.027(3) 0.041(3) 0.033(3) 0.016(3) 0.001(2) 0.001(2) C28 0.036(3) 0.053(4) 0.034(3) 0.016(3) 0.016(2) 0.019(3) C29 0.054(4) 0.044(3) 0.031(3) 0.004(3) 0.014(3) 0.001(3) C30 0.045(3) 0.042(3) 0.034(3) 0.009(3) 0.011(3) -0.004(3) C31 0.032(3) 0.038(3) 0.035(3) 0.015(3) 0.007(2) 0.002(2) C32 0.024(2) 0.027(2) 0.032(3) 0.009(2) 0.005(2) 0.005(2) C33 0.026(3) 0.032(3) 0.036(3) 0.008(2) 0.004(2) 0.004(2) C34 0.028(3) 0.039(3) 0.036(3) -0.004(3) -0.003(2) 0.006(2) C35 0.040(3) 0.056(4) 0.030(3) 0.006(3) 0.001(3) 0.019(3) C36 0.046(3) 0.047(3) 0.040(3) 0.018(3) 0.014(3) 0.013(3) C37 0.027(3) 0.032(3) 0.034(3) 0.007(2) 0.006(2) 0.002(2) C38 0.018(2) 0.053(3) 0.048(3) 0.030(3) 0.005(2) -0.001(2) C39 0.025(3) 0.045(3) 0.049(3) 0.027(3) 0.009(2) 0.001(2) C40 0.018(2) 0.034(3) 0.041(3) 0.016(2) 0.005(2) 0.000(2) C41 0.025(3) 0.030(3) 0.030(3) 0.007(2) 0.006(2) -0.003(2) C42 0.030(3) 0.094(5) 0.050(4) 0.039(4) 0.008(3) 0.004(3) C43 0.029(3) 0.061(4) 0.081(5) 0.044(4) 0.015(3) 0.000(3) C44 0.026(3) 0.049(4) 0.070(4) -0.007(3) 0.014(3) -0.006(3) C45 0.021(2) 0.035(3) 0.033(3) 0.014(2) 0.005(2) -0.004(2) C46 0.026(3) 0.037(3) 0.033(3) 0.011(2) -0.001(2) -0.004(2) C47 0.019(2) 0.040(3) 0.036(3) 0.020(3) 0.002(2) -0.001(2) C48 0.028(3) 0.075(5) 0.100(6) -0.005(4) 0.022(4) -0.010(3) C49 0.038(4) 0.073(5) 0.068(5) -0.004(4) 0.010(3) -0.002(3) C50 0.033(3) 0.049(3) 0.054(4) 0.015(3) 0.015(3) 0.005(3) C51 0.046(4) 0.055(4) 0.071(5) 0.004(4) 0.008(3) -0.003(3) B1 0.024(3) 0.034(3) 0.037(3) 0.011(3) 0.006(2) 0.000(2) B2 0.022(3) 0.037(3) 0.029(3) 0.011(3) 0.004(2) -0.004(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 Cl1 C51 1.764(7) . ? Cl2 C51 1.754(7) . ? F1 C2 1.337(6) . ? F2 C3 1.343(6) . ? F3 C4 1.347(6) . ? F4 C5 1.353(6) . ? F5 C6 1.357(6) . ? F6 C8 1.356(6) . ? F7 C9 1.347(7) . ? F8 C10 1.339(7) . ? F9 C11 1.343(7) . ? F10 C12 1.356(6) . ? F11 C17 1.318(7) . ? F12 C17 1.332(7) . ? F13 C17 1.336(7) . ? F14 C18 1.329(7) . ? F15 C18 1.312(7) . ? F16 C18 1.338(7) . ? F17 C27 1.358(6) . ? F18 C28 1.343(6) . ? F19 C29 1.351(6) . ? F20 C30 1.352(6) . ? F21 C31 1.359(6) . ? F22 C33 1.353(6) . ? F23 C34 1.340(6) . ? F24 C35 1.339(6) . ? F25 C36 1.345(6) . ? F26 C37 1.361(6) . ? F27 C42 1.342(8) . ? F28 C42 1.331(7) . ? F29 C42 1.329(7) . ? F30 C43 1.325(6) . ? F31 C43 1.355(7) . ? F32 C43 1.327(7) . ? O1 C13 1.386(6) . ? O1 B1 1.490(7) . ? O2 C38 1.383(6) . ? O2 B2 1.502(6) . ? N1 C22 1.286(7) . ? N1 C23 1.477(7) . ? N1 C19 1.485(7) . ? N2 C47 1.283(7) . ? N2 C44 1.457(7) . ? N2 C48 1.478(7) . ? C1 C6 1.383(7) . ? C1 C2 1.394(7) . ? C1 B1 1.679(8) . ? C2 C3 1.381(8) . ? C3 C4 1.370(8) . ? C4 C5 1.370(8) . ? C5 C6 1.382(7) . ? C7 C8 1.366(7) . ? C7 C12 1.385(8) . ? C7 B1 1.677(8) . ? C8 C9 1.387(8) . ? C9 C10 1.350(9) . ? C10 C11 1.356(9) . ? C11 C12 1.388(8) . ? C13 C18 1.537(8) . ? C13 C17 1.539(8) . ? C13 C14 1.545(7) . ? C14 C15 1.533(7) . ? C15 C20 1.491(7) . ? C15 C16 1.534(7) . ? C16 B1 1.618(7) . ? C19 C24 1.406(9) . ? C19 C20 1.484(8) . ? C20 C21 1.332(7) . ? C21 C22 1.442(7) . ? C22 C25 1.481(7) . ? C26 C31 1.375(7) . ? C26 C27 1.390(7) . ? C26 B2 1.674(8) . ? C27 C28 1.359(8) . ? C28 C29 1.377(8) . ? C29 C30 1.359(8) . ? C30 C31 1.380(8) . ? C32 C37 1.368(7) . ? C32 C33 1.390(7) . ? C32 B2 1.660(7) . ? C33 C34 1.384(7) . ? C34 C35 1.364(8) . ? C35 C36 1.369(8) . ? C36 C37 1.378(7) . ? C38 C42 1.533(8) . ? C38 C43 1.539(8) . ? C38 C39 1.545(7) . ? C39 C40 1.530(7) . ? C40 C45 1.490(7) . ? C40 C41 1.536(7) . ? C41 B2 1.618(7) . ? C44 C49 1.457(9) . ? C44 C45 1.493(7) . ? C45 C46 1.321(7) . ? C46 C47 1.431(7) . ? C47 C50 1.488(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 C13 O1 B1 125.7(4) . . ? C38 O2 B2 126.0(4) . . ? C22 N1 C23 128.3(5) . . ? C22 N1 C19 111.2(4) . . ? C23 N1 C19 120.5(5) . . ? C47 N2 C44 110.7(4) . . ? C47 N2 C48 128.1(5) . . ? C44 N2 C48 121.2(5) . . ? C6 C1 C2 113.0(5) . . ? C6 C1 B1 128.1(4) . . ? C2 C1 B1 118.8(5) . . ? F1 C2 C3 116.0(5) . . ? F1 C2 C1 119.4(5) . . ? C3 C2 C1 124.6(5) . . ? F2 C3 C4 120.2(5) . . ? F2 C3 C2 120.6(6) . . ? C4 C3 C2 119.2(5) . . ? F3 C4 C5 120.3(6) . . ? F3 C4 C3 120.6(5) . . ? C5 C4 C3 119.1(5) . . ? F4 C5 C4 119.6(5) . . ? F4 C5 C6 120.6(5) . . ? C4 C5 C6 119.8(5) . . ? F5 C6 C5 114.8(5) . . ? F5 C6 C1 121.0(4) . . ? C5 C6 C1 124.2(5) . . ? C8 C7 C12 112.9(5) . . ? C8 C7 B1 119.8(5) . . ? C12 C7 B1 127.1(5) . . ? F6 C8 C7 119.3(5) . . ? F6 C8 C9 115.7(5) . . ? C7 C8 C9 125.0(6) . . ? F7 C9 C10 120.6(6) . . ? F7 C9 C8 120.5(6) . . ? C10 C9 C8 119.0(6) . . ? F8 C10 C9 120.6(6) . . ? F8 C10 C11 119.6(6) . . ? C9 C10 C11 119.9(6) . . ? F9 C11 C10 121.2(5) . . ? F9 C11 C12 119.6(6) . . ? C10 C11 C12 119.1(6) . . ? F10 C12 C7 121.2(5) . . ? F10 C12 C11 114.7(5) . . ? C7 C12 C11 124.1(6) . . ? O1 C13 C18 105.5(4) . . ? O1 C13 C17 107.0(5) . . ? C18 C13 C17 109.0(4) . . ? O1 C13 C14 116.7(4) . . ? C18 C13 C14 107.4(5) . . ? C17 C13 C14 110.8(4) . . ? C15 C14 C13 112.8(4) . . ? C20 C15 C14 110.5(4) . . ? C20 C15 C16 110.0(4) . . ? C14 C15 C16 109.2(4) . . ? C15 C16 B1 110.6(4) . . ? F11 C17 F12 107.4(5) . . ? F11 C17 F13 105.7(5) . . ? F12 C17 F13 105.8(5) . . ? F11 C17 C13 111.8(4) . . ? F12 C17 C13 112.2(5) . . ? F13 C17 C13 113.4(5) . . ? F15 C18 F14 107.8(4) . . ? F15 C18 F16 106.5(5) . . ? F14 C18 F16 105.0(5) . . ? F15 C18 C13 114.2(5) . . ? F14 C18 C13 113.4(5) . . ? F16 C18 C13 109.4(4) . . ? C24 C19 C20 121.2(6) . . ? C24 C19 N1 114.6(6) . . ? C20 C19 N1 102.0(5) . . ? C21 C20 C19 108.0(4) . . ? C21 C20 C15 130.0(5) . . ? C19 C20 C15 121.6(4) . . ? C20 C21 C22 110.1(4) . . ? N1 C22 C21 108.4(4) . . ? N1 C22 C25 123.8(5) . . ? C21 C22 C25 127.6(5) . . ? C31 C26 C27 112.9(5) . . ? C31 C26 B2 128.2(4) . . ? C27 C26 B2 118.9(4) . . ? F17 C27 C28 116.1(5) . . ? F17 C27 C26 118.7(5) . . ? C28 C27 C26 125.2(5) . . ? F18 C28 C27 121.1(5) . . ? F18 C28 C29 120.2(5) . . ? C27 C28 C29 118.7(5) . . ? F19 C29 C30 120.8(5) . . ? F19 C29 C28 119.7(5) . . ? C30 C29 C28 119.5(5) . . ? F20 C30 C29 119.7(5) . . ? F20 C30 C31 121.0(5) . . ? C29 C30 C31 119.3(5) . . ? F21 C31 C26 121.6(5) . . ? F21 C31 C30 114.0(4) . . ? C26 C31 C30 124.4(5) . . ? C37 C32 C33 113.4(4) . . ? C37 C32 B2 119.5(4) . . ? C33 C32 B2 127.0(4) . . ? F22 C33 C34 114.8(4) . . ? F22 C33 C32 121.5(4) . . ? C34 C33 C32 123.7(5) . . ? F23 C34 C35 120.6(5) . . ? F23 C34 C33 120.1(5) . . ? C35 C34 C33 119.3(5) . . ? F24 C35 C34 120.2(5) . . ? F24 C35 C36 120.1(6) . . ? C34 C35 C36 119.7(5) . . ? F25 C36 C35 120.1(5) . . ? F25 C36 C37 121.3(5) . . ? C35 C36 C37 118.6(5) . . ? F26 C37 C32 119.4(4) . . ? F26 C37 C36 115.3(5) . . ? C32 C37 C36 125.2(5) . . ? O2 C38 C42 107.9(5) . . ? O2 C38 C43 104.6(4) . . ? C42 C38 C43 108.9(5) . . ? O2 C38 C39 116.8(4) . . ? C42 C38 C39 110.4(4) . . ? C43 C38 C39 108.0(5) . . ? C40 C39 C38 112.9(4) . . ? C45 C40 C39 110.9(4) . . ? C45 C40 C41 110.4(4) . . ? C39 C40 C41 109.4(4) . . ? C40 C41 B2 110.6(4) . . ? F29 C42 F28 105.9(5) . . ? F29 C42 F27 106.7(5) . . ? F28 C42 F27 106.3(6) . . ? F29 C42 C38 114.0(6) . . ? F28 C42 C38 112.7(5) . . ? F27 C42 C38 110.8(5) . . ? F30 C43 F32 106.2(5) . . ? F30 C43 F31 106.7(4) . . ? F32 C43 F31 106.2(5) . . ? F30 C43 C38 114.2(5) . . ? F32 C43 C38 110.5(4) . . ? F31 C43 C38 112.5(5) . . ? N2 C44 C49 115.2(5) . . ? N2 C44 C45 103.0(4) . . ? C49 C44 C45 118.7(5) . . ? C46 C45 C40 130.3(5) . . ? C46 C45 C44 106.7(4) . . ? C40 C45 C44 122.4(5) . . ? C45 C46 C47 110.6(5) . . ? N2 C47 C46 108.8(5) . . ? N2 C47 C50 124.0(4) . . ? C46 C47 C50 127.2(5) . . ? Cl2 C51 Cl1 111.4(4) . . ? O1 B1 C16 111.3(4) . . ? O1 B1 C7 106.9(4) . . ? C16 B1 C7 109.2(4) . . ? O1 B1 C1 107.1(4) . . ? C16 B1 C1 114.4(4) . . ? C7 B1 C1 107.8(4) . . ? O2 B2 C41 110.1(4) . . ? O2 B2 C32 107.0(4) . . ? C41 B2 C32 110.2(4) . . ? O2 B2 C26 107.4(4) . . ? C41 B2 C26 113.6(4) . . ? C32 B2 C26 108.1(4) . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 27.84 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.974 _refine_diff_density_min -1.129 _refine_diff_density_rms 0.095 #===end data_xz111_0m _database_code_depnum_ccdc_archive 'CCDC 870171' #TrackingRef '- all-CIFs.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H18 B F16 N O' _chemical_formula_weight 675.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.4047(7) _cell_length_b 11.0955(8) _cell_length_c 25.2965(19) _cell_angle_alpha 90.00 _cell_angle_beta 95.391(4) _cell_angle_gamma 90.00 _cell_volume 2628.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.707 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1352 _exptl_absorpt_coefficient_mu 0.182 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9611 _exptl_absorpt_correction_T_max 0.9892 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 42517 _diffrn_reflns_av_R_equivalents 0.0576 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 27.58 _reflns_number_total 6041 _reflns_number_gt 4018 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0387P)^2^+1.7882P] 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 6041 _refine_ls_number_parameters 409 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0831 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1089 _refine_ls_wR_factor_gt 0.0947 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F -0.03488(14) 0.11575(12) 0.06473(5) 0.0298(3) Uani 1 1 d . . . F2 F -0.20001(15) -0.05187(13) 0.01447(6) 0.0420(4) Uani 1 1 d . . . F3 F -0.26071(15) -0.25954(14) 0.06500(7) 0.0494(4) Uani 1 1 d . . . F4 F -0.14540(16) -0.29770(12) 0.16671(7) 0.0461(4) Uani 1 1 d . . . F5 F 0.02329(15) -0.13533(12) 0.21667(5) 0.0368(3) Uani 1 1 d . . . F6 F 0.19916(15) 0.32713(12) 0.10473(6) 0.0429(4) Uani 1 1 d . . . F7 F 0.41396(16) 0.31561(14) 0.04520(6) 0.0466(4) Uani 1 1 d . . . F8 F 0.57433(15) 0.11255(15) 0.04178(6) 0.0467(4) Uani 1 1 d . . . F9 F 0.51751(14) -0.07990(13) 0.10441(6) 0.0462(4) Uani 1 1 d . . . F10 F 0.30156(13) -0.07084(11) 0.16494(5) 0.0317(3) Uani 1 1 d . . . F11 F -0.25594(14) 0.11445(12) 0.18938(6) 0.0381(4) Uani 1 1 d . . . F12 F -0.33875(14) 0.29011(14) 0.20247(6) 0.0426(4) Uani 1 1 d . . . F13 F -0.26958(14) 0.24461(15) 0.12677(5) 0.0429(4) Uani 1 1 d . . . F14 F -0.15736(15) 0.46988(12) 0.22371(5) 0.0377(4) Uani 1 1 d . . . F15 F -0.12096(14) 0.44713(11) 0.14169(5) 0.0322(3) Uani 1 1 d . . . F16 F 0.05608(14) 0.45019(12) 0.20131(6) 0.0371(3) Uani 1 1 d . . . O1 O 0.00746(15) 0.22852(13) 0.16265(6) 0.0209(3) Uani 1 1 d . . . N1 N 0.17849(18) 0.11911(16) 0.40957(7) 0.0197(4) Uani 1 1 d . . . C1 C -0.0016(2) 0.00251(19) 0.14422(8) 0.0205(5) Uani 1 1 d . . . C2 C -0.0617(2) 0.01460(19) 0.09212(9) 0.0226(5) Uani 1 1 d . . . C3 C -0.1474(2) -0.0701(2) 0.06525(9) 0.0281(5) Uani 1 1 d . . . C4 C -0.1770(2) -0.1747(2) 0.09058(11) 0.0337(6) Uani 1 1 d . . . C5 C -0.1189(2) -0.1937(2) 0.14171(10) 0.0307(6) Uani 1 1 d . . . C6 C -0.0328(2) -0.1068(2) 0.16677(9) 0.0245(5) Uani 1 1 d . . . C7 C 0.2350(2) 0.12719(19) 0.13784(8) 0.0209(5) Uani 1 1 d . . . C8 C 0.2728(2) 0.2226(2) 0.10669(9) 0.0265(5) Uani 1 1 d . . . C9 C 0.3849(2) 0.2194(2) 0.07513(9) 0.0299(5) Uani 1 1 d . . . C10 C 0.4671(2) 0.1178(2) 0.07351(10) 0.0321(6) Uani 1 1 d . . . C11 C 0.4383(2) 0.0214(2) 0.10464(10) 0.0300(5) Uani 1 1 d . . . C12 C 0.3255(2) 0.0292(2) 0.13558(9) 0.0242(5) Uani 1 1 d . . . C13 C -0.0854(2) 0.27276(19) 0.19724(8) 0.0207(5) Uani 1 1 d . . . C14 C -0.0487(2) 0.2442(2) 0.25686(8) 0.0252(5) Uani 1 1 d . . . H14A H 0.0194 0.3056 0.2724 0.030 Uiso 1 1 calc R . . H14B H -0.1368 0.2507 0.2752 0.030 Uiso 1 1 calc R . . C15 C 0.0163(2) 0.1192(2) 0.26748(9) 0.0269(5) Uani 1 1 d . . . H15A H -0.0579 0.0576 0.2560 0.032 Uiso 1 1 calc R . . C16 C 0.1433(2) 0.1011(2) 0.23473(8) 0.0245(5) Uani 1 1 d . . . H16A H 0.1840 0.0196 0.2415 0.029 Uiso 1 1 calc R . . H16B H 0.2184 0.1610 0.2456 0.029 Uiso 1 1 calc R . . C17 C -0.2384(2) 0.2312(2) 0.17879(9) 0.0275(5) Uani 1 1 d . . . C18 C -0.0775(2) 0.4104(2) 0.19089(9) 0.0243(5) Uani 1 1 d . . . C19 C 0.1965(2) 0.1364(2) 0.35326(8) 0.0242(5) Uani 1 1 d . . . H19A H 0.2705 0.0816 0.3416 0.029 Uiso 1 1 calc R . . H19B H 0.2235 0.2206 0.3460 0.029 Uiso 1 1 calc R . . C20 C 0.0527(2) 0.1068(2) 0.32603(9) 0.0255(5) Uani 1 1 d . . . C21 C -0.0314(2) 0.0731(3) 0.36332(9) 0.0369(6) Uani 1 1 d . . . H21A H -0.1277 0.0467 0.3572 0.044 Uiso 1 1 calc R . . C22 C 0.0487(2) 0.0838(2) 0.41363(9) 0.0320(6) Uani 1 1 d . . . H22A H 0.0113 0.0670 0.4464 0.038 Uiso 1 1 calc R . . C23 C 0.2920(2) 0.1498(2) 0.45300(8) 0.0225(5) Uani 1 1 d . . . C24 C 0.4308(2) 0.0911(2) 0.43992(9) 0.0264(5) Uani 1 1 d . . . H24A H 0.4569 0.1217 0.4058 0.040 Uiso 1 1 calc R . . H24B H 0.4179 0.0035 0.4377 0.040 Uiso 1 1 calc R . . H24C H 0.5068 0.1101 0.4678 0.040 Uiso 1 1 calc R . . C25 C 0.3057(3) 0.2867(2) 0.45407(10) 0.0327(6) Uani 1 1 d . . . H25A H 0.3351 0.3149 0.4200 0.049 Uiso 1 1 calc R . . H25B H 0.3773 0.3106 0.4828 0.049 Uiso 1 1 calc R . . H25C H 0.2133 0.3226 0.4600 0.049 Uiso 1 1 calc R . . C26 C 0.2484(3) 0.1029(2) 0.50576(9) 0.0326(6) Uani 1 1 d . . . H26A H 0.2332 0.0156 0.5034 0.049 Uiso 1 1 calc R . . H26B H 0.1598 0.1424 0.5138 0.049 Uiso 1 1 calc R . . H26C H 0.3242 0.1204 0.5340 0.049 Uiso 1 1 calc R . . B1 B 0.0943(2) 0.1160(2) 0.17227(10) 0.0205(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 F1 0.0416(8) 0.0270(7) 0.0196(7) 0.0043(5) -0.0043(6) 0.0003(6) F2 0.0434(8) 0.0441(9) 0.0351(9) -0.0139(7) -0.0141(7) 0.0055(7) F3 0.0378(8) 0.0371(9) 0.0723(12) -0.0237(8) 0.0005(8) -0.0111(7) F4 0.0540(9) 0.0210(8) 0.0661(11) 0.0033(7) 0.0209(8) -0.0094(7) F5 0.0541(9) 0.0277(8) 0.0288(8) 0.0101(6) 0.0053(7) -0.0005(6) F6 0.0436(8) 0.0268(8) 0.0618(10) 0.0172(7) 0.0233(7) 0.0101(6) F7 0.0450(9) 0.0444(9) 0.0537(10) 0.0122(8) 0.0215(7) -0.0071(7) F8 0.0319(8) 0.0583(10) 0.0532(10) -0.0142(8) 0.0224(7) -0.0062(7) F9 0.0300(7) 0.0394(9) 0.0705(11) -0.0101(8) 0.0117(7) 0.0126(6) F10 0.0318(7) 0.0243(7) 0.0386(8) 0.0040(6) 0.0020(6) 0.0078(6) F11 0.0303(7) 0.0305(8) 0.0538(10) 0.0055(7) 0.0059(7) -0.0087(6) F12 0.0235(7) 0.0508(10) 0.0543(10) -0.0037(8) 0.0085(7) 0.0096(6) F13 0.0341(8) 0.0636(11) 0.0288(8) 0.0067(7) -0.0086(6) -0.0168(7) F14 0.0518(9) 0.0259(7) 0.0373(8) -0.0035(6) 0.0146(7) 0.0125(6) F15 0.0441(8) 0.0234(7) 0.0290(8) 0.0072(6) 0.0023(6) 0.0053(6) F16 0.0340(8) 0.0256(7) 0.0505(9) -0.0044(7) -0.0025(7) -0.0069(6) O1 0.0241(7) 0.0204(8) 0.0186(8) 0.0019(6) 0.0045(6) 0.0050(6) N1 0.0221(9) 0.0226(10) 0.0144(9) 0.0011(7) 0.0014(7) 0.0028(7) C1 0.0209(10) 0.0211(11) 0.0204(11) 0.0008(9) 0.0063(9) 0.0056(8) C2 0.0235(11) 0.0189(11) 0.0257(12) 0.0001(9) 0.0035(9) 0.0035(9) C3 0.0249(11) 0.0309(13) 0.0273(13) -0.0070(11) -0.0036(10) 0.0063(10) C4 0.0215(11) 0.0275(13) 0.0523(17) -0.0168(12) 0.0047(11) -0.0031(10) C5 0.0302(12) 0.0208(12) 0.0431(16) 0.0003(11) 0.0132(11) -0.0006(10) C6 0.0272(11) 0.0223(12) 0.0249(12) 0.0017(10) 0.0071(9) 0.0030(9) C7 0.0206(10) 0.0206(11) 0.0207(11) -0.0025(9) -0.0025(9) 0.0007(9) C8 0.0254(11) 0.0227(12) 0.0315(13) -0.0015(10) 0.0028(10) 0.0006(9) C9 0.0274(12) 0.0338(14) 0.0291(13) 0.0017(11) 0.0061(10) -0.0078(10) C10 0.0203(11) 0.0438(15) 0.0332(14) -0.0090(12) 0.0074(10) -0.0050(10) C11 0.0210(11) 0.0290(13) 0.0394(14) -0.0122(11) 0.0004(10) 0.0045(10) C12 0.0227(11) 0.0223(12) 0.0269(12) -0.0010(10) -0.0017(9) -0.0010(9) C13 0.0222(10) 0.0200(11) 0.0201(11) 0.0011(9) 0.0038(9) 0.0039(9) C14 0.0296(12) 0.0261(12) 0.0199(12) 0.0016(9) 0.0030(9) 0.0044(10) C15 0.0288(12) 0.0287(13) 0.0226(12) 0.0001(10) -0.0005(10) 0.0021(10) C16 0.0264(11) 0.0241(12) 0.0224(12) -0.0016(9) -0.0009(9) 0.0040(9) C17 0.0268(11) 0.0284(13) 0.0277(13) 0.0023(10) 0.0057(10) -0.0001(10) C18 0.0274(11) 0.0224(12) 0.0231(12) -0.0011(9) 0.0029(9) 0.0043(9) C19 0.0293(12) 0.0285(12) 0.0150(11) 0.0006(9) 0.0028(9) 0.0011(9) C20 0.0256(11) 0.0284(13) 0.0216(12) 0.0000(10) -0.0028(9) 0.0075(9) C21 0.0244(12) 0.0584(18) 0.0269(13) 0.0030(12) -0.0035(10) -0.0048(11) C22 0.0264(12) 0.0461(15) 0.0236(13) 0.0081(11) 0.0031(10) -0.0008(11) C23 0.0240(11) 0.0279(12) 0.0148(11) -0.0021(9) -0.0021(9) 0.0029(9) C24 0.0238(11) 0.0317(13) 0.0232(12) 0.0000(10) 0.0001(9) 0.0007(10) C25 0.0417(14) 0.0274(13) 0.0276(13) -0.0083(11) -0.0047(11) -0.0011(11) C26 0.0305(12) 0.0485(16) 0.0185(12) 0.0031(11) 0.0000(10) 0.0065(11) B1 0.0223(12) 0.0202(13) 0.0190(12) 0.0002(10) 0.0017(10) 0.0047(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 C2 1.355(2) . ? F2 C3 1.348(3) . ? F3 C4 1.352(3) . ? F4 C5 1.350(3) . ? F5 C6 1.359(3) . ? F6 C8 1.349(3) . ? F7 C9 1.351(3) . ? F8 C10 1.348(2) . ? F9 C11 1.349(3) . ? F10 C12 1.366(3) . ? F11 C17 1.336(3) . ? F12 C17 1.335(3) . ? F13 C17 1.329(3) . ? F14 C18 1.344(2) . ? F15 C18 1.337(2) . ? F16 C18 1.335(3) . ? O1 C13 1.383(2) . ? O1 B1 1.499(3) . ? N1 C22 1.295(3) . ? N1 C19 1.463(3) . ? N1 C23 1.497(3) . ? C1 C6 1.383(3) . ? C1 C2 1.391(3) . ? C1 B1 1.668(3) . ? C2 C3 1.375(3) . ? C3 C4 1.367(3) . ? C4 C5 1.372(4) . ? C5 C6 1.376(3) . ? C7 C8 1.386(3) . ? C7 C12 1.386(3) . ? C7 B1 1.656(3) . ? C8 C9 1.382(3) . ? C9 C10 1.370(3) . ? C10 C11 1.370(4) . ? C11 C12 1.379(3) . ? C13 C18 1.538(3) . ? C13 C17 1.541(3) . ? C13 C14 1.548(3) . ? C14 C15 1.530(3) . ? C15 C20 1.495(3) . ? C15 C16 1.529(3) . ? C16 B1 1.612(3) . ? C19 C20 1.496(3) . ? C20 C21 1.340(3) . ? C21 C22 1.422(3) . ? C23 C24 1.523(3) . ? C23 C25 1.524(3) . ? C23 C26 1.524(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O1 B1 124.04(16) . . ? C22 N1 C19 108.24(18) . . ? C22 N1 C23 128.53(18) . . ? C19 N1 C23 123.01(17) . . ? C6 C1 C2 113.1(2) . . ? C6 C1 B1 127.83(19) . . ? C2 C1 B1 119.05(18) . . ? F1 C2 C3 116.21(19) . . ? F1 C2 C1 119.05(19) . . ? C3 C2 C1 124.7(2) . . ? F2 C3 C4 120.1(2) . . ? F2 C3 C2 121.0(2) . . ? C4 C3 C2 118.9(2) . . ? F3 C4 C3 120.1(2) . . ? F3 C4 C5 120.4(2) . . ? C3 C4 C5 119.5(2) . . ? F4 C5 C4 119.9(2) . . ? F4 C5 C6 120.7(2) . . ? C4 C5 C6 119.4(2) . . ? F5 C6 C5 115.2(2) . . ? F5 C6 C1 120.6(2) . . ? C5 C6 C1 124.3(2) . . ? C8 C7 C12 112.63(19) . . ? C8 C7 B1 128.06(19) . . ? C12 C7 B1 119.18(19) . . ? F6 C8 C9 114.7(2) . . ? F6 C8 C7 121.30(19) . . ? C9 C8 C7 124.0(2) . . ? F7 C9 C10 119.3(2) . . ? F7 C9 C8 120.6(2) . . ? C10 C9 C8 120.1(2) . . ? F8 C10 C11 120.6(2) . . ? F8 C10 C9 120.6(2) . . ? C11 C10 C9 118.8(2) . . ? F9 C11 C10 120.6(2) . . ? F9 C11 C12 120.6(2) . . ? C10 C11 C12 118.8(2) . . ? F10 C12 C11 115.67(19) . . ? F10 C12 C7 118.81(18) . . ? C11 C12 C7 125.5(2) . . ? O1 C13 C18 104.31(16) . . ? O1 C13 C17 109.22(17) . . ? C18 C13 C17 108.56(17) . . ? O1 C13 C14 116.58(17) . . ? C18 C13 C14 107.23(17) . . ? C17 C13 C14 110.51(17) . . ? C15 C14 C13 113.92(18) . . ? C20 C15 C16 114.03(18) . . ? C20 C15 C14 107.93(18) . . ? C16 C15 C14 110.07(18) . . ? C15 C16 B1 110.58(17) . . ? F13 C17 F12 106.83(18) . . ? F13 C17 F11 106.69(19) . . ? F12 C17 F11 106.19(17) . . ? F13 C17 C13 112.28(17) . . ? F12 C17 C13 113.38(19) . . ? F11 C17 C13 111.04(18) . . ? F16 C18 F15 106.41(17) . . ? F16 C18 F14 106.60(18) . . ? F15 C18 F14 106.60(17) . . ? F16 C18 C13 111.20(17) . . ? F15 C18 C13 112.75(18) . . ? F14 C18 C13 112.85(17) . . ? N1 C19 C20 103.73(17) . . ? C21 C20 C15 128.9(2) . . ? C21 C20 C19 107.75(19) . . ? C15 C20 C19 123.29(19) . . ? C20 C21 C22 108.0(2) . . ? N1 C22 C21 112.3(2) . . ? N1 C23 C24 108.03(17) . . ? N1 C23 C25 107.03(17) . . ? C24 C23 C25 110.98(19) . . ? N1 C23 C26 109.43(18) . . ? C24 C23 C26 110.51(18) . . ? C25 C23 C26 110.75(19) . . ? O1 B1 C16 110.23(17) . . ? O1 B1 C7 107.60(17) . . ? C16 B1 C7 110.73(17) . . ? O1 B1 C1 107.17(17) . . ? C16 B1 C1 115.64(18) . . ? C7 B1 C1 105.05(16) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.58 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.561 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.058 #===end data_xz116_0m-sr _database_code_depnum_ccdc_archive 'CCDC 870172' #TrackingRef '- all-CIFs.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H22 B F16 N2 O' _chemical_formula_weight 729.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.7955(4) _cell_length_b 17.5647(6) _cell_length_c 20.0048(7) _cell_angle_alpha 67.7060(10) _cell_angle_beta 77.8810(10) _cell_angle_gamma 89.5610(10) _cell_volume 3420.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1468 _exptl_absorpt_coefficient_mu 0.146 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9728 _exptl_absorpt_correction_T_max 0.9855 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 49240 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.26 _diffrn_reflns_theta_max 25.00 _reflns_number_total 12010 _reflns_number_gt 7561 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1123P)^2^+6.3315P] 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 12010 _refine_ls_number_parameters 883 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1217 _refine_ls_R_factor_gt 0.0856 _refine_ls_wR_factor_ref 0.2489 _refine_ls_wR_factor_gt 0.2303 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.4411(5) 0.5572(3) 0.2476(4) 0.0483(16) Uani 1 1 d . . . B2 B 0.1334(5) 0.9427(3) 0.7453(3) 0.0367(13) Uani 1 1 d . . . N1 N 0.8515(3) 0.4435(2) 0.2262(2) 0.0386(10) Uani 1 1 d . . . N2 N 0.8432(3) 0.4600(2) 0.3304(2) 0.0370(9) Uani 1 1 d . . . N3 N 0.5979(3) 1.0435(2) 0.6712(2) 0.0319(9) Uani 1 1 d . . . N4 N 0.5147(3) 1.0546(2) 0.7765(2) 0.0319(8) Uani 1 1 d . . . O1 O 0.3650(3) 0.47562(18) 0.2881(2) 0.0476(9) Uani 1 1 d . . . O2 O 0.0877(3) 1.02489(17) 0.70589(18) 0.0361(8) Uani 1 1 d . . . F1 F 0.1745(2) 0.57692(15) 0.29779(16) 0.0427(7) Uani 1 1 d . . . F2 F 0.0716(3) 0.66241(17) 0.37656(18) 0.0537(8) Uani 1 1 d . . . F3 F 0.2230(4) 0.75567(18) 0.41526(19) 0.0671(10) Uani 1 1 d . . . F4 F 0.4799(4) 0.76308(19) 0.3689(2) 0.0772(11) Uani 1 1 d . . . F5 F 0.5862(3) 0.67719(18) 0.2901(2) 0.0681(10) Uani 1 1 d . . . F6 F 0.2557(3) 0.49306(18) 0.17814(18) 0.0627(9) Uani 1 1 d . . . F7 F 0.2053(4) 0.5746(2) 0.0469(2) 0.0824(11) Uani 1 1 d . . . F8 F 0.3238(5) 0.7277(3) -0.0422(2) 0.1002(14) Uani 1 1 d . . . F9 F 0.4956(5) 0.7959(2) 0.0064(2) 0.0935(14) Uani 1 1 d . . . F10 F 0.5467(3) 0.71490(17) 0.13823(18) 0.0611(9) Uani 1 1 d . . . F11 F 0.4023(3) 0.4670(2) 0.42548(19) 0.0634(9) Uani 1 1 d . . . F12 F 0.2236(3) 0.4104(3) 0.4298(2) 0.0842(12) Uani 1 1 d . . . F13 F 0.3720(3) 0.3349(2) 0.46995(17) 0.0643(9) Uani 1 1 d . . . F14 F 0.2165(3) 0.33443(17) 0.3378(2) 0.0605(9) Uani 1 1 d . . . F15 F 0.3686(3) 0.26035(15) 0.37466(18) 0.0558(8) Uani 1 1 d . . . F16 F 0.3870(3) 0.33720(19) 0.26007(18) 0.0571(8) Uani 1 1 d . . . F17 F -0.0965(2) 0.92208(15) 0.70028(15) 0.0387(6) Uani 1 1 d . . . F18 F -0.1385(3) 0.84133(17) 0.61827(17) 0.0521(8) Uani 1 1 d . . . F19 F 0.0444(3) 0.75075(18) 0.57414(18) 0.0659(9) Uani 1 1 d . . . F20 F 0.2692(3) 0.74384(19) 0.61654(19) 0.0709(10) Uani 1 1 d . . . F21 F 0.3173(3) 0.82812(18) 0.69523(18) 0.0610(9) Uani 1 1 d . . . F22 F -0.1056(3) 1.00766(19) 0.81609(16) 0.0556(8) Uani 1 1 d . . . F23 F -0.2543(3) 0.9278(2) 0.94772(19) 0.0739(10) Uani 1 1 d . . . F24 F -0.2047(4) 0.7757(2) 1.03686(18) 0.0864(12) Uani 1 1 d . . . F25 F 0.0047(4) 0.70523(19) 0.98942(18) 0.0846(12) Uani 1 1 d . . . F26 F 0.1563(3) 0.78447(16) 0.85545(16) 0.0556(8) Uani 1 1 d . . . F27 F 0.2464(3) 1.02847(19) 0.57294(17) 0.0565(8) Uani 1 1 d . . . F28 F 0.0639(3) 1.0778(2) 0.56507(18) 0.0739(11) Uani 1 1 d . . . F29 F 0.2340(3) 1.1599(2) 0.52304(17) 0.0650(9) Uani 1 1 d . . . F30 F -0.0251(3) 1.16428(19) 0.6484(3) 0.0863(13) Uani 1 1 d . . . F31 F 0.1524(3) 1.23989(17) 0.6110(2) 0.0709(10) Uani 1 1 d . . . F32 F 0.0764(3) 1.1693(2) 0.7266(2) 0.0754(11) Uani 1 1 d . . . C1 C 0.3862(4) 0.6184(3) 0.2923(3) 0.0392(12) Uani 1 1 d . . . C2 C 0.2565(5) 0.6214(3) 0.3153(3) 0.0395(12) Uani 1 1 d . . . C3 C 0.1979(5) 0.6654(3) 0.3560(3) 0.0409(12) Uani 1 1 d . . . C4 C 0.2768(6) 0.7140(3) 0.3733(3) 0.0518(15) Uani 1 1 d . . . C5 C 0.4049(6) 0.7163(3) 0.3501(3) 0.0538(16) Uani 1 1 d . . . C6 C 0.4574(5) 0.6695(3) 0.3106(3) 0.0465(13) Uani 1 1 d . . . C7 C 0.4047(5) 0.5991(3) 0.1664(3) 0.0461(13) Uani 1 1 d . . . C8 C 0.3190(5) 0.5680(3) 0.1378(3) 0.0521(14) Uani 1 1 d . . . C9 C 0.2891(6) 0.6094(4) 0.0695(3) 0.0622(16) Uani 1 1 d . . . C10 C 0.3491(7) 0.6860(4) 0.0243(4) 0.0703(18) Uani 1 1 d . . . C11 C 0.4363(7) 0.7201(3) 0.0490(3) 0.0643(18) Uani 1 1 d . . . C12 C 0.4609(5) 0.6776(3) 0.1165(3) 0.0503(14) Uani 1 1 d . . . C13 C 0.4046(4) 0.4057(2) 0.3389(3) 0.0314(10) Uani 1 1 d . . . C14 C 0.5479(4) 0.3965(3) 0.3274(2) 0.0293(9) Uani 1 1 d . . . H14A H 0.5676 0.3659 0.3764 0.035 Uiso 1 1 calc R . . H14B H 0.5701 0.3625 0.2975 0.035 Uiso 1 1 calc R . . C15 C 0.6316(4) 0.4765(3) 0.2898(3) 0.0435(12) Uani 1 1 d . . . C16 C 0.5956(5) 0.5447(3) 0.2266(4) 0.0627(16) Uani 1 1 d . . . C17 C 0.3484(5) 0.4036(3) 0.4162(3) 0.0481(13) Uani 1 1 d . . . C18 C 0.3428(4) 0.3340(3) 0.3286(3) 0.0399(12) Uani 1 1 d . . . C19 C 0.7734(4) 0.4612(3) 0.2811(3) 0.0340(10) Uani 1 1 d . . . C20 C 0.9682(5) 0.4315(3) 0.2446(4) 0.0557(15) Uani 1 1 d . . . H20A H 1.0412 0.4184 0.2163 0.067 Uiso 1 1 calc R . . C21 C 0.9635(5) 0.4410(3) 0.3067(4) 0.0548(15) Uani 1 1 d . . . H21A H 1.0315 0.4356 0.3312 0.066 Uiso 1 1 calc R . . C22 C 0.8332(5) 0.4414(3) 0.1531(3) 0.0474(13) Uani 1 1 d . . . C23 C 0.7168(5) 0.3882(4) 0.1630(3) 0.0510(14) Uani 1 1 d . . . H23A H 0.6408 0.4112 0.1820 0.077 Uiso 1 1 calc R . . H23B H 0.7219 0.3321 0.1983 0.077 Uiso 1 1 calc R . . H23C H 0.7118 0.3867 0.1152 0.077 Uiso 1 1 calc R . . C24 C 0.8450(9) 0.5313(4) 0.0989(3) 0.088(2) Uani 1 1 d . . . H24A H 0.7746 0.5599 0.1158 0.132 Uiso 1 1 calc R . . H24B H 0.8421 0.5334 0.0496 0.132 Uiso 1 1 calc R . . H24C H 0.9259 0.5582 0.0965 0.132 Uiso 1 1 calc R . . C25 C 0.9464(6) 0.4015(5) 0.1225(4) 0.088(3) Uani 1 1 d . . . H25A H 0.9423 0.3430 0.1547 0.133 Uiso 1 1 calc R . . H25B H 1.0259 0.4294 0.1208 0.133 Uiso 1 1 calc R . . H25C H 0.9431 0.4067 0.0724 0.133 Uiso 1 1 calc R . . C26 C 0.8093(5) 0.4790(3) 0.4004(3) 0.0446(13) Uani 1 1 d . . . C27 C 0.7958(8) 0.5715(3) 0.3765(4) 0.079(2) Uani 1 1 d . . . H27A H 0.7744 0.5853 0.4204 0.119 Uiso 1 1 calc R . . H27B H 0.7282 0.5868 0.3490 0.119 Uiso 1 1 calc R . . H27C H 0.8762 0.6019 0.3446 0.119 Uiso 1 1 calc R . . C28 C 0.6925(5) 0.4260(4) 0.4534(3) 0.0539(14) Uani 1 1 d . . . H28A H 0.7080 0.3676 0.4666 0.081 Uiso 1 1 calc R . . H28B H 0.6200 0.4380 0.4297 0.081 Uiso 1 1 calc R . . H28C H 0.6738 0.4381 0.4983 0.081 Uiso 1 1 calc R . . C29 C 0.9194(6) 0.4574(4) 0.4402(4) 0.0635(17) Uani 1 1 d . . . H29A H 0.9297 0.3982 0.4557 0.095 Uiso 1 1 calc R . . H29B H 0.9009 0.4718 0.4839 0.095 Uiso 1 1 calc R . . H29C H 0.9979 0.4886 0.4064 0.095 Uiso 1 1 calc R . . C30 C 0.1144(4) 0.8830(2) 0.6999(3) 0.0343(11) Uani 1 1 d . . . C31 C 0.0004(4) 0.8801(2) 0.6794(2) 0.0312(10) Uani 1 1 d . . . C32 C -0.0264(4) 0.8379(3) 0.6378(3) 0.0389(11) Uani 1 1 d . . . C33 C 0.0664(6) 0.7918(3) 0.6161(3) 0.0495(14) Uani 1 1 d . . . C34 C 0.1795(5) 0.7902(3) 0.6373(3) 0.0471(14) Uani 1 1 d . . . C35 C 0.2007(4) 0.8336(3) 0.6777(3) 0.0419(12) Uani 1 1 d . . . C36 C 0.0355(4) 0.9007(3) 0.8268(3) 0.0366(11) Uani 1 1 d . . . C37 C -0.0714(5) 0.9331(3) 0.8552(3) 0.0400(11) Uani 1 1 d . . . C38 C -0.1514(5) 0.8920(4) 0.9245(3) 0.0522(14) Uani 1 1 d . . . C39 C -0.1274(6) 0.8162(3) 0.9697(3) 0.0584(16) Uani 1 1 d . . . C40 C -0.0229(6) 0.7815(3) 0.9458(3) 0.0535(15) Uani 1 1 d . . . C41 C 0.0545(5) 0.8228(3) 0.8771(3) 0.0444(12) Uani 1 1 d . . . C42 C 0.1628(4) 1.0940(2) 0.6562(2) 0.0296(10) Uani 1 1 d . . . C43 C 0.2966(4) 1.1055(2) 0.6687(2) 0.0281(9) Uani 1 1 d . . . H43A H 0.3532 1.1386 0.6202 0.034 Uiso 1 1 calc R . . H43B H 0.2912 1.1376 0.7004 0.034 Uiso 1 1 calc R . . C44 C 0.3569(4) 1.0260(3) 0.7041(3) 0.0430(13) Uani 1 1 d . . . C45 C 0.2732(5) 0.9551(3) 0.7649(4) 0.0601(16) Uani 1 1 d . . . C46 C 0.1777(5) 1.0912(3) 0.5771(3) 0.0474(13) Uani 1 1 d . . . C47 C 0.0913(5) 1.1664(3) 0.6602(4) 0.0546(15) Uani 1 1 d . . . C48 C 0.4855(4) 1.0414(2) 0.7186(2) 0.0303(10) Uani 1 1 d . . . C49 C 0.6966(4) 1.0557(3) 0.7010(3) 0.0377(11) Uani 1 1 d . . . H49A H 0.7847 1.0589 0.6797 0.045 Uiso 1 1 calc R . . C50 C 0.6456(5) 1.0621(3) 0.7648(3) 0.0423(12) Uani 1 1 d . . . H50A H 0.6917 1.0705 0.7974 0.051 Uiso 1 1 calc R . . C51 C 0.6267(4) 1.0300(3) 0.5987(3) 0.0351(11) Uani 1 1 d . . . C52 C 0.5946(5) 0.9397(3) 0.6149(4) 0.0588(17) Uani 1 1 d . . . H52A H 0.6407 0.9049 0.6513 0.088 Uiso 1 1 calc R . . H52B H 0.6194 0.9298 0.5691 0.088 Uiso 1 1 calc R . . H52C H 0.5030 0.9262 0.6349 0.088 Uiso 1 1 calc R . . C53 C 0.5573(5) 1.0894(4) 0.5434(3) 0.0569(15) Uani 1 1 d . . . H53A H 0.4653 1.0786 0.5636 0.085 Uiso 1 1 calc R . . H53B H 0.5786 1.0812 0.4966 0.085 Uiso 1 1 calc R . . H53C H 0.5833 1.1463 0.5345 0.085 Uiso 1 1 calc R . . C54 C 0.7675(4) 1.0517(3) 0.5634(3) 0.0445(12) Uani 1 1 d . . . H54A H 0.8172 1.0155 0.5968 0.067 Uiso 1 1 calc R . . H54B H 0.7894 1.1093 0.5544 0.067 Uiso 1 1 calc R . . H54C H 0.7867 1.0442 0.5163 0.067 Uiso 1 1 calc R . . C55 C 0.4323(5) 1.0553(3) 0.8489(3) 0.0414(12) Uani 1 1 d . . . C56 C 0.3214(5) 1.1072(4) 0.8366(3) 0.0532(14) Uani 1 1 d . . . H56A H 0.2625 1.0823 0.8181 0.080 Uiso 1 1 calc R . . H56B H 0.3520 1.1629 0.8002 0.080 Uiso 1 1 calc R . . H56C H 0.2774 1.1103 0.8836 0.080 Uiso 1 1 calc R . . C57 C 0.4076(8) 0.9669(3) 0.9040(3) 0.074(2) Uani 1 1 d . . . H57A H 0.3546 0.9359 0.8872 0.111 Uiso 1 1 calc R . . H57B H 0.3636 0.9655 0.9526 0.111 Uiso 1 1 calc R . . H57C H 0.4886 0.9419 0.9079 0.111 Uiso 1 1 calc R . . C58 C 0.5193(6) 1.0990(4) 0.8802(4) 0.0716(19) Uani 1 1 d . . . H58A H 0.4716 1.1002 0.9272 0.107 Uiso 1 1 calc R . . H58B H 0.5456 1.1556 0.8445 0.107 Uiso 1 1 calc R . . H58C H 0.5946 1.0684 0.8884 0.107 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.027(3) 0.022(3) 0.086(5) -0.011(3) -0.010(3) 0.001(2) B2 0.025(3) 0.020(2) 0.057(4) -0.005(2) -0.012(2) 0.000(2) N1 0.026(2) 0.028(2) 0.055(3) -0.0165(18) 0.0058(18) 0.0015(15) N2 0.024(2) 0.0277(19) 0.055(3) -0.0079(18) -0.0151(18) 0.0025(15) N3 0.030(2) 0.0233(18) 0.045(2) -0.0117(17) -0.0172(18) 0.0003(15) N4 0.036(2) 0.0271(19) 0.042(2) -0.0174(17) -0.0188(17) 0.0034(15) O1 0.0323(18) 0.0189(15) 0.080(3) -0.0036(16) -0.0190(17) 0.0002(13) O2 0.0189(15) 0.0207(15) 0.056(2) -0.0023(14) -0.0057(14) -0.0022(12) F1 0.0288(14) 0.0379(14) 0.075(2) -0.0302(14) -0.0244(13) 0.0068(11) F2 0.0536(19) 0.0451(17) 0.080(2) -0.0380(16) -0.0263(16) 0.0146(14) F3 0.097(3) 0.0437(17) 0.080(2) -0.0297(17) -0.049(2) 0.0069(17) F4 0.101(3) 0.0432(18) 0.096(3) -0.0148(18) -0.062(2) -0.0211(17) F5 0.0435(18) 0.0446(17) 0.102(3) -0.0003(17) -0.0403(18) -0.0167(14) F6 0.0489(19) 0.0480(18) 0.074(2) -0.0057(16) -0.0119(16) -0.0159(14) F7 0.087(3) 0.082(3) 0.080(3) -0.033(2) -0.018(2) -0.014(2) F8 0.154(4) 0.085(3) 0.048(2) -0.011(2) -0.021(2) -0.006(3) F9 0.153(4) 0.046(2) 0.058(2) -0.0070(17) 0.002(2) -0.027(2) F10 0.067(2) 0.0336(16) 0.069(2) -0.0145(15) 0.0059(17) -0.0118(14) F11 0.060(2) 0.075(2) 0.081(2) -0.058(2) -0.0194(17) 0.0242(17) F12 0.0305(18) 0.145(4) 0.093(3) -0.070(3) -0.0022(17) 0.016(2) F13 0.060(2) 0.075(2) 0.0426(18) -0.0167(17) 0.0082(15) -0.0071(17) F14 0.0288(16) 0.0425(17) 0.110(3) -0.0290(17) -0.0167(16) -0.0048(12) F15 0.0521(18) 0.0197(14) 0.083(2) -0.0079(14) -0.0119(16) -0.0018(12) F16 0.063(2) 0.0586(19) 0.065(2) -0.0365(17) -0.0229(17) 0.0074(15) F17 0.0248(13) 0.0363(14) 0.0602(17) -0.0259(13) -0.0068(12) 0.0064(11) F18 0.0527(19) 0.0453(16) 0.070(2) -0.0343(15) -0.0150(15) 0.0002(13) F19 0.094(3) 0.0398(17) 0.061(2) -0.0276(16) 0.0046(18) 0.0058(16) F20 0.068(2) 0.0499(18) 0.072(2) -0.0167(16) 0.0164(17) 0.0291(16) F21 0.0279(16) 0.0530(18) 0.076(2) -0.0041(16) 0.0031(14) 0.0166(13) F22 0.0389(17) 0.0569(19) 0.0532(18) -0.0044(15) -0.0052(14) 0.0115(14) F23 0.064(2) 0.085(3) 0.062(2) -0.0272(19) 0.0067(17) 0.0058(19) F24 0.122(3) 0.071(2) 0.043(2) -0.0121(18) 0.010(2) -0.013(2) F25 0.153(4) 0.0378(18) 0.046(2) -0.0011(15) -0.017(2) 0.011(2) F26 0.081(2) 0.0287(14) 0.0538(18) -0.0083(13) -0.0231(16) 0.0093(14) F27 0.0511(19) 0.061(2) 0.060(2) -0.0348(16) 0.0034(15) -0.0087(15) F28 0.049(2) 0.111(3) 0.058(2) -0.024(2) -0.0181(16) -0.0237(19) F29 0.060(2) 0.073(2) 0.0430(18) -0.0006(16) -0.0122(15) -0.0142(17) F30 0.0367(18) 0.0429(18) 0.188(4) -0.042(2) -0.049(2) 0.0150(14) F31 0.058(2) 0.0257(15) 0.116(3) -0.0113(17) -0.024(2) 0.0036(14) F32 0.052(2) 0.085(3) 0.110(3) -0.070(2) 0.0005(19) 0.0093(17) C1 0.037(3) 0.017(2) 0.054(3) 0.005(2) -0.025(2) -0.0038(18) C2 0.040(3) 0.024(2) 0.059(3) -0.013(2) -0.028(2) -0.0008(19) C3 0.041(3) 0.027(2) 0.060(3) -0.013(2) -0.027(2) 0.006(2) C4 0.093(5) 0.021(2) 0.056(3) -0.016(2) -0.043(3) 0.006(3) C5 0.063(4) 0.029(3) 0.066(4) 0.002(3) -0.045(3) -0.016(2) C6 0.044(3) 0.025(2) 0.066(4) -0.002(2) -0.032(3) -0.002(2) C7 0.036(3) 0.029(2) 0.060(3) -0.014(2) 0.010(2) 0.003(2) C8 0.037(3) 0.041(3) 0.071(4) -0.024(3) 0.006(3) -0.003(2) C9 0.069(4) 0.059(4) 0.053(4) -0.023(3) 0.000(3) 0.009(3) C10 0.090(5) 0.051(4) 0.061(4) -0.024(3) 0.005(4) -0.006(3) C11 0.099(5) 0.032(3) 0.037(3) -0.003(3) 0.018(3) -0.007(3) C12 0.053(3) 0.030(3) 0.062(4) -0.023(3) 0.011(3) -0.008(2) C13 0.027(2) 0.017(2) 0.047(3) -0.0085(19) -0.008(2) 0.0003(17) C14 0.027(2) 0.029(2) 0.034(2) -0.0166(19) -0.0020(19) 0.0005(17) C15 0.028(3) 0.030(2) 0.047(3) 0.007(2) 0.003(2) 0.0007(19) C16 0.045(3) 0.042(3) 0.085(4) -0.007(3) -0.015(3) 0.009(2) C17 0.032(3) 0.060(3) 0.052(3) -0.026(3) 0.002(2) 0.009(2) C18 0.033(3) 0.023(2) 0.063(3) -0.014(2) -0.012(2) 0.0004(19) C19 0.029(2) 0.023(2) 0.042(3) -0.006(2) -0.006(2) 0.0026(18) C20 0.024(3) 0.044(3) 0.097(5) -0.031(3) -0.001(3) 0.007(2) C21 0.029(3) 0.041(3) 0.099(5) -0.029(3) -0.019(3) 0.008(2) C22 0.059(3) 0.036(3) 0.034(3) -0.013(2) 0.014(2) -0.002(2) C23 0.052(3) 0.073(4) 0.036(3) -0.031(3) -0.007(2) 0.009(3) C24 0.156(7) 0.051(4) 0.040(3) -0.016(3) 0.010(4) 0.000(4) C25 0.064(4) 0.100(5) 0.115(6) -0.081(5) 0.030(4) -0.012(4) C26 0.050(3) 0.037(3) 0.065(3) -0.026(3) -0.038(3) 0.011(2) C27 0.137(6) 0.044(3) 0.099(5) -0.041(3) -0.088(5) 0.028(4) C28 0.051(3) 0.080(4) 0.052(3) -0.043(3) -0.023(3) 0.016(3) C29 0.060(4) 0.058(4) 0.075(4) -0.011(3) -0.047(3) 0.001(3) C30 0.024(2) 0.019(2) 0.043(3) -0.0001(19) 0.005(2) 0.0005(17) C31 0.028(2) 0.017(2) 0.041(3) -0.0085(19) 0.0039(19) 0.0007(17) C32 0.031(3) 0.026(2) 0.053(3) -0.013(2) -0.001(2) 0.0008(19) C33 0.077(4) 0.020(2) 0.037(3) -0.009(2) 0.014(3) 0.002(2) C34 0.040(3) 0.030(3) 0.048(3) 0.002(2) 0.007(2) 0.016(2) C35 0.033(3) 0.025(2) 0.049(3) -0.005(2) 0.012(2) 0.0017(19) C36 0.040(3) 0.030(2) 0.043(3) -0.011(2) -0.021(2) -0.009(2) C37 0.038(3) 0.039(3) 0.046(3) -0.013(2) -0.020(2) -0.001(2) C38 0.056(4) 0.056(3) 0.043(3) -0.020(3) -0.007(3) -0.007(3) C39 0.091(5) 0.048(3) 0.032(3) -0.016(3) -0.003(3) -0.012(3) C40 0.095(5) 0.029(3) 0.031(3) -0.003(2) -0.020(3) -0.005(3) C41 0.061(3) 0.029(2) 0.051(3) -0.018(2) -0.023(3) 0.004(2) C42 0.026(2) 0.019(2) 0.037(3) -0.0034(18) -0.0071(19) -0.0030(17) C43 0.023(2) 0.022(2) 0.036(2) -0.0076(18) -0.0068(18) -0.0015(16) C44 0.035(3) 0.026(2) 0.062(3) 0.000(2) -0.031(2) -0.0083(19) C45 0.032(3) 0.037(3) 0.096(5) -0.004(3) -0.024(3) -0.009(2) C46 0.031(3) 0.044(3) 0.059(3) -0.005(3) -0.021(2) -0.014(2) C47 0.037(3) 0.032(3) 0.099(5) -0.028(3) -0.020(3) 0.004(2) C48 0.032(3) 0.020(2) 0.038(3) -0.0075(19) -0.015(2) 0.0017(17) C49 0.031(3) 0.035(2) 0.056(3) -0.019(2) -0.024(2) 0.0033(19) C50 0.035(3) 0.041(3) 0.062(3) -0.025(3) -0.026(2) 0.007(2) C51 0.030(2) 0.038(3) 0.046(3) -0.026(2) -0.010(2) 0.0019(19) C52 0.038(3) 0.051(3) 0.093(4) -0.051(3) 0.018(3) -0.012(2) C53 0.042(3) 0.090(4) 0.048(3) -0.034(3) -0.016(3) 0.009(3) C54 0.033(3) 0.042(3) 0.051(3) -0.014(2) -0.004(2) -0.006(2) C55 0.065(3) 0.036(3) 0.033(3) -0.018(2) -0.021(2) 0.005(2) C56 0.052(3) 0.075(4) 0.035(3) -0.025(3) -0.009(2) 0.014(3) C57 0.131(6) 0.045(3) 0.037(3) -0.013(3) -0.004(4) 0.002(4) C58 0.075(4) 0.098(5) 0.083(5) -0.073(4) -0.031(4) 0.019(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 O1 1.497(6) . ? B1 C7 1.640(9) . ? B1 C16 1.666(8) . ? B1 C1 1.674(8) . ? B2 O2 1.496(6) . ? B2 C36 1.641(7) . ? B2 C30 1.665(7) . ? B2 C45 1.672(7) . ? N1 C19 1.371(6) . ? N1 C20 1.379(7) . ? N1 C22 1.529(7) . ? N2 C19 1.357(6) . ? N2 C21 1.370(6) . ? N2 C26 1.531(7) . ? N3 C48 1.365(6) . ? N3 C49 1.380(5) . ? N3 C51 1.526(6) . ? N4 C48 1.361(6) . ? N4 C50 1.382(6) . ? N4 C55 1.537(6) . ? O1 C13 1.397(5) . ? O2 C42 1.372(5) . ? F1 C2 1.366(5) . ? F2 C3 1.334(6) . ? F3 C4 1.355(6) . ? F4 C5 1.359(5) . ? F5 C6 1.357(6) . ? F6 C8 1.352(6) . ? F7 C9 1.336(7) . ? F8 C10 1.340(8) . ? F9 C11 1.352(6) . ? F10 C12 1.367(6) . ? F11 C17 1.352(6) . ? F12 C17 1.331(6) . ? F13 C17 1.343(6) . ? F14 C18 1.338(5) . ? F15 C18 1.341(5) . ? F16 C18 1.332(6) . ? F17 C31 1.361(5) . ? F18 C32 1.341(6) . ? F19 C33 1.352(6) . ? F20 C34 1.359(5) . ? F21 C35 1.370(6) . ? F22 C37 1.342(5) . ? F23 C38 1.356(7) . ? F24 C39 1.350(6) . ? F25 C40 1.364(6) . ? F26 C41 1.364(6) . ? F27 C46 1.343(6) . ? F28 C46 1.339(5) . ? F29 C46 1.319(6) . ? F30 C47 1.330(6) . ? F31 C47 1.359(6) . ? F32 C47 1.324(7) . ? C1 C6 1.383(7) . ? C1 C2 1.386(7) . ? C2 C3 1.383(7) . ? C3 C4 1.391(7) . ? C4 C5 1.358(8) . ? C5 C6 1.384(8) . ? C7 C8 1.396(8) . ? C7 C12 1.408(7) . ? C8 C9 1.387(8) . ? C9 C10 1.375(9) . ? C10 C11 1.385(10) . ? C11 C12 1.355(8) . ? C13 C17 1.524(7) . ? C13 C18 1.531(6) . ? C13 C14 1.533(6) . ? C14 C15 1.513(6) . ? C15 C16 1.495(7) . ? C15 C19 1.538(6) . ? C20 C21 1.305(8) . ? C22 C23 1.505(8) . ? C22 C24 1.526(8) . ? C22 C25 1.536(8) . ? C26 C28 1.513(8) . ? C26 C27 1.524(7) . ? C26 C29 1.533(7) . ? C30 C31 1.384(6) . ? C30 C35 1.388(6) . ? C31 C32 1.377(7) . ? C32 C33 1.385(7) . ? C33 C34 1.370(8) . ? C34 C35 1.355(8) . ? C36 C37 1.393(7) . ? C36 C41 1.402(7) . ? C37 C38 1.390(7) . ? C38 C39 1.356(8) . ? C39 C40 1.364(9) . ? C40 C41 1.372(8) . ? C42 C47 1.501(6) . ? C42 C43 1.544(6) . ? C42 C46 1.576(7) . ? C43 C44 1.518(6) . ? C44 C45 1.501(7) . ? C44 C48 1.523(6) . ? C49 C50 1.327(7) . ? C51 C52 1.519(6) . ? C51 C54 1.519(6) . ? C51 C53 1.528(7) . ? C55 C56 1.504(7) . ? C55 C57 1.511(7) . ? C55 C58 1.576(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 O1 B1 C7 107.2(4) . . ? O1 B1 C16 111.1(4) . . ? C7 B1 C16 103.5(5) . . ? O1 B1 C1 107.2(4) . . ? C7 B1 C1 105.2(4) . . ? C16 B1 C1 121.7(5) . . ? O2 B2 C36 107.0(4) . . ? O2 B2 C30 107.5(4) . . ? C36 B2 C30 105.8(3) . . ? O2 B2 C45 110.2(4) . . ? C36 B2 C45 104.2(4) . . ? C30 B2 C45 121.2(4) . . ? C19 N1 C20 106.5(4) . . ? C19 N1 C22 132.8(4) . . ? C20 N1 C22 120.5(4) . . ? C19 N2 C21 108.4(4) . . ? C19 N2 C26 131.0(4) . . ? C21 N2 C26 120.6(4) . . ? C48 N3 C49 108.8(4) . . ? C48 N3 C51 131.4(3) . . ? C49 N3 C51 119.7(4) . . ? C48 N4 C50 107.7(4) . . ? C48 N4 C55 132.4(4) . . ? C50 N4 C55 119.6(4) . . ? C13 O1 B1 125.0(4) . . ? C42 O2 B2 125.9(3) . . ? C6 C1 C2 112.6(5) . . ? C6 C1 B1 127.0(5) . . ? C2 C1 B1 120.4(4) . . ? F1 C2 C3 114.3(4) . . ? F1 C2 C1 119.0(4) . . ? C3 C2 C1 126.7(4) . . ? F2 C3 C2 121.6(4) . . ? F2 C3 C4 121.6(5) . . ? C2 C3 C4 116.8(5) . . ? F3 C4 C5 121.9(5) . . ? F3 C4 C3 118.5(5) . . ? C5 C4 C3 119.7(5) . . ? C4 C5 F4 118.4(6) . . ? C4 C5 C6 120.5(4) . . ? F4 C5 C6 121.0(5) . . ? F5 C6 C1 121.1(5) . . ? F5 C6 C5 115.3(4) . . ? C1 C6 C5 123.7(5) . . ? C8 C7 C12 111.7(5) . . ? C8 C7 B1 128.6(4) . . ? C12 C7 B1 119.7(5) . . ? F6 C8 C9 115.0(5) . . ? F6 C8 C7 120.0(5) . . ? C9 C8 C7 125.0(5) . . ? F7 C9 C10 120.2(6) . . ? F7 C9 C8 120.6(5) . . ? C10 C9 C8 119.2(6) . . ? F8 C10 C9 121.2(7) . . ? F8 C10 C11 119.9(6) . . ? C9 C10 C11 118.9(6) . . ? F9 C11 C12 120.1(6) . . ? F9 C11 C10 120.3(6) . . ? C12 C11 C10 119.6(5) . . ? C11 C12 F10 116.9(5) . . ? C11 C12 C7 125.7(6) . . ? F10 C12 C7 117.4(5) . . ? O1 C13 C17 107.5(4) . . ? O1 C13 C18 103.6(4) . . ? C17 C13 C18 109.7(4) . . ? O1 C13 C14 116.9(4) . . ? C17 C13 C14 111.3(4) . . ? C18 C13 C14 107.5(3) . . ? C15 C14 C13 115.3(3) . . ? C16 C15 C14 118.9(4) . . ? C16 C15 C19 116.5(4) . . ? C14 C15 C19 111.7(4) . . ? C15 C16 B1 110.1(5) . . ? F12 C17 F13 107.9(4) . . ? F12 C17 F11 106.3(4) . . ? F13 C17 F11 105.6(4) . . ? F12 C17 C13 114.1(4) . . ? F13 C17 C13 112.5(4) . . ? F11 C17 C13 110.0(4) . . ? F16 C18 F14 106.0(4) . . ? F16 C18 F15 106.4(4) . . ? F14 C18 F15 107.8(4) . . ? F16 C18 C13 110.4(4) . . ? F14 C18 C13 113.5(4) . . ? F15 C18 C13 112.3(4) . . ? N2 C19 N1 107.3(4) . . ? N2 C19 C15 124.3(4) . . ? N1 C19 C15 128.4(4) . . ? C21 C20 N1 109.7(5) . . ? C20 C21 N2 108.1(5) . . ? C23 C22 C24 117.8(6) . . ? C23 C22 N1 112.7(4) . . ? C24 C22 N1 106.1(4) . . ? C23 C22 C25 105.7(4) . . ? C24 C22 C25 106.0(5) . . ? N1 C22 C25 108.1(5) . . ? C28 C26 C27 113.9(5) . . ? C28 C26 N2 110.8(4) . . ? C27 C26 N2 107.9(4) . . ? C28 C26 C29 107.2(4) . . ? C27 C26 C29 108.5(4) . . ? N2 C26 C29 108.5(4) . . ? C31 C30 C35 112.4(4) . . ? C31 C30 B2 119.2(4) . . ? C35 C30 B2 128.4(4) . . ? F17 C31 C32 114.6(4) . . ? F17 C31 C30 119.6(4) . . ? C32 C31 C30 125.8(4) . . ? F18 C32 C31 121.4(4) . . ? F18 C32 C33 120.6(5) . . ? C31 C32 C33 118.0(5) . . ? F19 C33 C34 121.7(5) . . ? F19 C33 C32 119.7(5) . . ? C34 C33 C32 118.5(5) . . ? C35 C34 F20 121.3(5) . . ? C35 C34 C33 120.7(4) . . ? F20 C34 C33 118.0(5) . . ? C34 C35 F21 115.8(4) . . ? C34 C35 C30 124.4(5) . . ? F21 C35 C30 119.8(5) . . ? C37 C36 C41 111.8(5) . . ? C37 C36 B2 127.8(4) . . ? C41 C36 B2 120.4(4) . . ? F22 C37 C38 114.7(5) . . ? F22 C37 C36 121.3(4) . . ? C38 C37 C36 124.0(5) . . ? C39 C38 F23 119.1(5) . . ? C39 C38 C37 120.7(6) . . ? F23 C38 C37 120.2(5) . . ? F24 C39 C38 121.1(6) . . ? F24 C39 C40 120.5(5) . . ? C38 C39 C40 118.4(5) . . ? C39 C40 F25 120.4(5) . . ? C39 C40 C41 120.0(5) . . ? F25 C40 C41 119.6(5) . . ? F26 C41 C40 117.5(4) . . ? F26 C41 C36 117.4(5) . . ? C40 C41 C36 125.1(5) . . ? O2 C42 C47 106.1(4) . . ? O2 C42 C43 117.0(3) . . ? C47 C42 C43 108.0(4) . . ? O2 C42 C46 107.0(3) . . ? C47 C42 C46 110.2(4) . . ? C43 C42 C46 108.5(3) . . ? C44 C43 C42 115.1(3) . . ? C45 C44 C43 118.0(4) . . ? C45 C44 C48 115.0(4) . . ? C43 C44 C48 112.5(3) . . ? C44 C45 B2 112.2(4) . . ? F29 C46 F28 108.0(4) . . ? F29 C46 F27 108.1(4) . . ? F28 C46 F27 107.2(4) . . ? F29 C46 C42 112.9(4) . . ? F28 C46 C42 110.6(4) . . ? F27 C46 C42 109.9(4) . . ? F32 C47 F30 105.8(5) . . ? F32 C47 F31 106.2(4) . . ? F30 C47 F31 107.1(5) . . ? F32 C47 C42 111.2(5) . . ? F30 C47 C42 113.4(4) . . ? F31 C47 C42 112.7(5) . . ? N4 C48 N3 107.0(4) . . ? N4 C48 C44 130.2(4) . . ? N3 C48 C44 122.8(4) . . ? C50 C49 N3 107.3(4) . . ? C49 C50 N4 109.1(4) . . ? C52 C51 C54 109.1(4) . . ? C52 C51 N3 109.2(4) . . ? C54 C51 N3 108.8(4) . . ? C52 C51 C53 113.5(4) . . ? C54 C51 C53 105.8(4) . . ? N3 C51 C53 110.2(4) . . ? C56 C55 C57 118.8(5) . . ? C56 C55 N4 112.8(4) . . ? C57 C55 N4 107.3(4) . . ? C56 C55 C58 105.7(4) . . ? C57 C55 C58 105.4(5) . . ? N4 C55 C58 106.0(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.451 _refine_diff_density_min -0.536 _refine_diff_density_rms 0.076 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 0.000 310 99 ' ' 2 0.500 0.500 0.000 310 99 ' ' _platon_squeeze_details ; During the refinement of the structure, electron density peaks were located that were believed to be highly disordered solvent molecules (possibly dichloromethane). Attempts made to model the solvent molecule were not successful. The SQUEEZE option in PLATON (Spek, 2003) indicated there was a large solvent cavity. In the final cycles of refinement, this contribution to the electron density was removed from the observed data. The density, the F(000) value, the molecular weight and the formula are given without taking into account the results obtained with the SQUEEZE option PLATON (Spek, 2003). Similar treatments of disordered solvent molecules were carried out by St\"ahler et al. (2001), Cox et al. (2003), Mohamed et al. (2003) and Athimoolam et al. (2005). References: Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13 Athimoolam, S., Kumar, J., Ramakrishnan, V. & Rajaram, R.K. (2005). Acta Cryst. E61, m2014-m2017. Cox, J.P., Kumarasammy, Y., Nahar, L., Sarkar D.S. & Shoeb, M. (2003). Acta Cryst. E59, o975-o977. Mohamed, A.A., Krause Bauer, A.J., Bruce, E.A. & Bruce M.R.M. (2003). Acta Cryst. C59, m84-m86. St\"ahler, R., N\"ather, C. & Bensch, W. (2001). Acta Cryst. C57, 26-27. ; _iucr_refine_instructions_details ; TITL XZ116_0m in P-1 CELL 0.71073 10.7955 17.5647 20.0048 67.706 77.881 89.561 ZERR 4.00 0.0004 0.0006 0.0007 0.001 0.001 0.001 LATT 1 SFAC C H N O B F UNIT 116 88 8 4 4 64 L.S. 8 ACTA FMAP 2 PLAN 10 SIZE 0.100 0.160 0.190 omit -3 50 omit 0 2 1 omit 1 3 3 omit 0 0 1 omit 2 3 2 omit 1 3 2 omit 0 4 0 omit 1 -1 1 omit -2 0 2 omit -2 6 7 omit -1 1 0 omit 2 5 2 TEMP -123.140 WGHT 0.112300 6.331501 FVAR 1.19557 B1 5 0.441072 0.557164 0.247593 11.00000 0.02687 0.02191 = 0.08608 -0.01096 -0.01035 0.00137 B2 5 0.133379 0.942703 0.745348 11.00000 0.02493 0.02031 = 0.05749 -0.00523 -0.01216 -0.00004 N1 3 0.851465 0.443465 0.226205 11.00000 0.02565 0.02824 = 0.05515 -0.01649 0.00584 0.00151 N2 3 0.843222 0.460044 0.330427 11.00000 0.02429 0.02766 = 0.05470 -0.00791 -0.01508 0.00250 N3 3 0.597851 1.043514 0.671174 11.00000 0.02977 0.02327 = 0.04536 -0.01172 -0.01723 0.00030 N4 3 0.514678 1.054637 0.776493 11.00000 0.03574 0.02710 = 0.04160 -0.01742 -0.01878 0.00341 O1 4 0.364951 0.475624 0.288055 11.00000 0.03226 0.01895 = 0.08039 -0.00364 -0.01899 0.00023 O2 4 0.087676 1.024886 0.705887 11.00000 0.01885 0.02072 = 0.05605 -0.00230 -0.00575 -0.00222 F1 6 0.174481 0.576921 0.297792 11.00000 0.02882 0.03786 = 0.07502 -0.03024 -0.02439 0.00679 F2 6 0.071626 0.662412 0.376563 11.00000 0.05363 0.04515 = 0.08020 -0.03797 -0.02632 0.01462 F3 6 0.223040 0.755668 0.415262 11.00000 0.09720 0.04367 = 0.07964 -0.02974 -0.04887 0.00693 F4 6 0.479868 0.763083 0.368936 11.00000 0.10114 0.04318 = 0.09592 -0.01477 -0.06235 -0.02111 F5 6 0.586156 0.677190 0.290052 11.00000 0.04354 0.04462 = 0.10236 -0.00028 -0.04027 -0.01669 F6 6 0.255660 0.493063 0.178144 11.00000 0.04891 0.04796 = 0.07431 -0.00575 -0.01193 -0.01590 F7 6 0.205286 0.574584 0.046946 11.00000 0.08709 0.08157 = 0.08003 -0.03279 -0.01811 -0.01407 F8 6 0.323804 0.727723 -0.042230 11.00000 0.15448 0.08450 = 0.04808 -0.01114 -0.02117 -0.00561 F9 6 0.495562 0.795866 0.006367 11.00000 0.15273 0.04613 = 0.05781 -0.00695 0.00231 -0.02687 F10 6 0.546740 0.714896 0.138234 11.00000 0.06655 0.03364 = 0.06864 -0.01453 0.00589 -0.01184 F11 6 0.402263 0.467042 0.425476 11.00000 0.06050 0.07526 = 0.08112 -0.05811 -0.01937 0.02416 F12 6 0.223631 0.410421 0.429789 11.00000 0.03050 0.14498 = 0.09347 -0.07014 -0.00217 0.01591 F13 6 0.372045 0.334920 0.469949 11.00000 0.05998 0.07545 = 0.04262 -0.01674 0.00820 -0.00712 F14 6 0.216500 0.334430 0.337795 11.00000 0.02880 0.04252 = 0.11032 -0.02895 -0.01674 -0.00480 F15 6 0.368618 0.260349 0.374661 11.00000 0.05212 0.01969 = 0.08319 -0.00791 -0.01191 -0.00183 F16 6 0.386989 0.337196 0.260073 11.00000 0.06338 0.05864 = 0.06482 -0.03648 -0.02292 0.00738 F17 6 -0.096506 0.922081 0.700277 11.00000 0.02483 0.03635 = 0.06019 -0.02585 -0.00678 0.00637 F18 6 -0.138477 0.841329 0.618266 11.00000 0.05271 0.04535 = 0.06986 -0.03426 -0.01499 0.00016 F19 6 0.044406 0.750749 0.574138 11.00000 0.09426 0.03980 = 0.06060 -0.02761 0.00462 0.00576 F20 6 0.269177 0.743836 0.616536 11.00000 0.06834 0.04987 = 0.07227 -0.01669 0.01642 0.02912 F21 6 0.317319 0.828122 0.695225 11.00000 0.02792 0.05296 = 0.07574 -0.00405 0.00313 0.01662 F22 6 -0.105557 1.007662 0.816092 11.00000 0.03889 0.05685 = 0.05323 -0.00444 -0.00520 0.01152 F23 6 -0.254303 0.927750 0.947723 11.00000 0.06373 0.08513 = 0.06184 -0.02717 0.00669 0.00577 F24 6 -0.204735 0.775720 1.036856 11.00000 0.12213 0.07108 = 0.04327 -0.01212 0.01047 -0.01329 F25 6 0.004684 0.705226 0.989425 11.00000 0.15343 0.03778 = 0.04615 -0.00105 -0.01669 0.01098 F26 6 0.156292 0.784465 0.855447 11.00000 0.08102 0.02872 = 0.05383 -0.00832 -0.02307 0.00928 F27 6 0.246418 1.028469 0.572941 11.00000 0.05108 0.06117 = 0.06027 -0.03484 0.00337 -0.00872 F28 6 0.063889 1.077807 0.565074 11.00000 0.04851 0.11137 = 0.05750 -0.02411 -0.01815 -0.02365 F29 6 0.233988 1.159859 0.523039 11.00000 0.06004 0.07270 = 0.04304 -0.00059 -0.01224 -0.01421 F30 6 -0.025052 1.164276 0.648352 11.00000 0.03670 0.04291 = 0.18826 -0.04240 -0.04866 0.01497 F31 6 0.152426 1.239892 0.610981 11.00000 0.05781 0.02573 = 0.11644 -0.01130 -0.02353 0.00356 F32 6 0.076369 1.169268 0.726569 11.00000 0.05180 0.08456 = 0.11028 -0.06979 0.00046 0.00928 C1 1 0.386183 0.618357 0.292273 11.00000 0.03689 0.01728 = 0.05375 0.00462 -0.02469 -0.00377 C2 1 0.256517 0.621437 0.315296 11.00000 0.04045 0.02398 = 0.05944 -0.01310 -0.02790 -0.00077 C3 1 0.197858 0.665386 0.355972 11.00000 0.04082 0.02705 = 0.05952 -0.01335 -0.02740 0.00633 C4 1 0.276849 0.713955 0.373285 11.00000 0.09256 0.02092 = 0.05569 -0.01616 -0.04299 0.00568 C5 1 0.404908 0.716272 0.350080 11.00000 0.06275 0.02891 = 0.06591 0.00230 -0.04492 -0.01647 C6 1 0.457353 0.669520 0.310614 11.00000 0.04362 0.02543 = 0.06564 -0.00165 -0.03215 -0.00247 C7 1 0.404665 0.599080 0.166430 11.00000 0.03568 0.02942 = 0.06038 -0.01415 0.00991 0.00309 C8 1 0.318965 0.568044 0.137759 11.00000 0.03737 0.04068 = 0.07149 -0.02391 0.00645 -0.00292 C9 1 0.289149 0.609355 0.069489 11.00000 0.06855 0.05869 = 0.05345 -0.02265 0.00026 0.00929 C10 1 0.349071 0.685951 0.024350 11.00000 0.09028 0.05146 = 0.06105 -0.02403 0.00458 -0.00561 C11 1 0.436319 0.720135 0.048976 11.00000 0.09865 0.03191 = 0.03709 -0.00315 0.01849 -0.00676 C12 1 0.460930 0.677607 0.116530 11.00000 0.05314 0.02989 = 0.06194 -0.02323 0.01051 -0.00764 C13 1 0.404556 0.405734 0.338884 11.00000 0.02703 0.01657 = 0.04705 -0.00855 -0.00796 0.00029 C14 1 0.547909 0.396459 0.327421 11.00000 0.02654 0.02878 = 0.03443 -0.01660 -0.00200 0.00045 AFIX 23 H14A 2 0.567636 0.365891 0.376391 11.00000 -1.20000 H14B 2 0.570050 0.362483 0.297507 11.00000 -1.20000 AFIX 0 C15 1 0.631575 0.476503 0.289767 11.00000 0.02764 0.03041 = 0.04698 0.00681 0.00345 0.00072 C16 1 0.595566 0.544705 0.226550 11.00000 0.04462 0.04168 = 0.08540 -0.00657 -0.01461 0.00880 C17 1 0.348369 0.403573 0.416161 11.00000 0.03161 0.06006 = 0.05165 -0.02640 0.00205 0.00904 C18 1 0.342833 0.333967 0.328570 11.00000 0.03251 0.02280 = 0.06282 -0.01387 -0.01215 0.00036 C19 1 0.773405 0.461192 0.281077 11.00000 0.02921 0.02314 = 0.04241 -0.00592 -0.00603 0.00264 C20 1 0.968228 0.431507 0.244602 11.00000 0.02352 0.04386 = 0.09683 -0.03056 -0.00140 0.00706 AFIX 43 H20A 2 1.041170 0.418351 0.216341 11.00000 -1.20000 AFIX 0 C21 1 0.963451 0.440989 0.306710 11.00000 0.02893 0.04061 = 0.09890 -0.02887 -0.01906 0.00798 AFIX 43 H21A 2 1.031459 0.435615 0.331186 11.00000 -1.20000 AFIX 0 C22 1 0.833179 0.441441 0.153143 11.00000 0.05877 0.03630 = 0.03445 -0.01264 0.01425 -0.00170 C23 1 0.716778 0.388242 0.162991 11.00000 0.05162 0.07322 = 0.03608 -0.03124 -0.00720 0.00949 AFIX 33 H23A 2 0.640800 0.411241 0.181953 11.00000 -1.50000 H23B 2 0.721904 0.332134 0.198281 11.00000 -1.50000 H23C 2 0.711842 0.386713 0.115151 11.00000 -1.50000 AFIX 0 C24 1 0.844981 0.531271 0.098928 11.00000 0.15561 0.05140 = 0.03970 -0.01623 0.01048 0.00049 AFIX 33 H24A 2 0.774561 0.559892 0.115844 11.00000 -1.50000 H24B 2 0.842094 0.533360 0.049628 11.00000 -1.50000 H24C 2 0.925868 0.558248 0.096494 11.00000 -1.50000 AFIX 0 C25 1 0.946374 0.401505 0.122500 11.00000 0.06353 0.09951 = 0.11460 -0.08082 0.03012 -0.01169 AFIX 33 H25A 2 0.942326 0.342974 0.154720 11.00000 -1.50000 H25B 2 1.025907 0.429389 0.120849 11.00000 -1.50000 H25C 2 0.943104 0.406675 0.072383 11.00000 -1.50000 AFIX 0 C26 1 0.809305 0.479043 0.400428 11.00000 0.04985 0.03650 = 0.06510 -0.02581 -0.03809 0.01092 C27 1 0.795823 0.571510 0.376493 11.00000 0.13688 0.04373 = 0.09882 -0.04078 -0.08784 0.02804 AFIX 33 H27A 2 0.774436 0.585344 0.420417 11.00000 -1.50000 H27B 2 0.728176 0.586756 0.349042 11.00000 -1.50000 H27C 2 0.876190 0.601873 0.344632 11.00000 -1.50000 AFIX 0 C28 1 0.692490 0.426020 0.453424 11.00000 0.05100 0.07995 = 0.05240 -0.04328 -0.02313 0.01600 AFIX 33 H28A 2 0.707985 0.367621 0.466594 11.00000 -1.50000 H28B 2 0.620008 0.438038 0.429658 11.00000 -1.50000 H28C 2 0.673813 0.438056 0.498348 11.00000 -1.50000 AFIX 0 C29 1 0.919403 0.457431 0.440199 11.00000 0.05980 0.05792 = 0.07454 -0.01090 -0.04675 0.00090 AFIX 33 H29A 2 0.929715 0.398156 0.455663 11.00000 -1.50000 H29B 2 0.900929 0.471751 0.483907 11.00000 -1.50000 H29C 2 0.997938 0.488573 0.406449 11.00000 -1.50000 AFIX 0 C30 1 0.114372 0.883013 0.699932 11.00000 0.02432 0.01949 = 0.04250 -0.00013 0.00451 0.00045 C31 1 0.000370 0.880092 0.679354 11.00000 0.02774 0.01733 = 0.04061 -0.00846 0.00394 0.00070 C32 1 -0.026377 0.837945 0.637752 11.00000 0.03121 0.02555 = 0.05338 -0.01267 -0.00082 0.00083 C33 1 0.066380 0.791794 0.616117 11.00000 0.07682 0.02034 = 0.03697 -0.00917 0.01350 0.00177 C34 1 0.179500 0.790205 0.637254 11.00000 0.03960 0.02989 = 0.04782 0.00208 0.00732 0.01573 C35 1 0.200691 0.833626 0.677686 11.00000 0.03297 0.02547 = 0.04887 -0.00493 0.01162 0.00173 C36 1 0.035520 0.900720 0.826779 11.00000 0.04022 0.02953 = 0.04283 -0.01085 -0.02090 -0.00942 C37 1 -0.071405 0.933107 0.855244 11.00000 0.03787 0.03870 = 0.04577 -0.01313 -0.02000 -0.00134 C38 1 -0.151363 0.892042 0.924471 11.00000 0.05594 0.05631 = 0.04290 -0.01970 -0.00651 -0.00659 C39 1 -0.127439 0.816203 0.969676 11.00000 0.09112 0.04766 = 0.03234 -0.01631 -0.00305 -0.01250 C40 1 -0.022894 0.781456 0.945764 11.00000 0.09517 0.02922 = 0.03097 -0.00310 -0.01956 -0.00499 C41 1 0.054466 0.822830 0.877126 11.00000 0.06145 0.02878 = 0.05061 -0.01825 -0.02281 0.00440 C42 1 0.162796 1.094042 0.656176 11.00000 0.02621 0.01895 = 0.03693 -0.00338 -0.00714 -0.00296 C43 1 0.296608 1.105520 0.668665 11.00000 0.02332 0.02160 = 0.03614 -0.00757 -0.00679 -0.00146 AFIX 23 H43A 2 0.353245 1.138649 0.620234 11.00000 -1.20000 H43B 2 0.291155 1.137576 0.700446 11.00000 -1.20000 AFIX 0 C44 1 0.356903 1.026029 0.704130 11.00000 0.03522 0.02625 = 0.06225 -0.00050 -0.03094 -0.00826 C45 1 0.273153 0.955135 0.764940 11.00000 0.03200 0.03720 = 0.09606 -0.00390 -0.02396 -0.00941 C46 1 0.177678 1.091184 0.577130 11.00000 0.03063 0.04421 = 0.05917 -0.00486 -0.02090 -0.01386 C47 1 0.091327 1.166368 0.660203 11.00000 0.03718 0.03206 = 0.09917 -0.02802 -0.01988 0.00358 C48 1 0.485540 1.041374 0.718608 11.00000 0.03204 0.02001 = 0.03847 -0.00755 -0.01452 0.00172 C49 1 0.696553 1.055709 0.700975 11.00000 0.03111 0.03497 = 0.05566 -0.01936 -0.02439 0.00332 AFIX 43 H49A 2 0.784709 1.058925 0.679706 11.00000 -1.20000 AFIX 0 C50 1 0.645554 1.062115 0.764849 11.00000 0.03494 0.04129 = 0.06208 -0.02473 -0.02596 0.00721 AFIX 43 H50A 2 0.691662 1.070503 0.797369 11.00000 -1.20000 AFIX 0 C51 1 0.626713 1.029952 0.598671 11.00000 0.03021 0.03823 = 0.04642 -0.02623 -0.00961 0.00185 C52 1 0.594589 0.939722 0.614944 11.00000 0.03775 0.05106 = 0.09341 -0.05124 0.01799 -0.01194 AFIX 33 H52A 2 0.640704 0.904941 0.651305 11.00000 -1.50000 H52B 2 0.619385 0.929833 0.569088 11.00000 -1.50000 H52C 2 0.502956 0.926184 0.634935 11.00000 -1.50000 AFIX 0 C53 1 0.557266 1.089359 0.543410 11.00000 0.04172 0.08988 = 0.04845 -0.03414 -0.01597 0.00916 AFIX 33 H53A 2 0.465342 1.078623 0.563630 11.00000 -1.50000 H53B 2 0.578623 1.081236 0.496606 11.00000 -1.50000 H53C 2 0.583281 1.146330 0.534544 11.00000 -1.50000 AFIX 0 C54 1 0.767510 1.051692 0.563406 11.00000 0.03334 0.04236 = 0.05120 -0.01372 -0.00392 -0.00557 AFIX 33 H54A 2 0.817201 1.015544 0.596790 11.00000 -1.50000 H54B 2 0.789436 1.109315 0.554410 11.00000 -1.50000 H54C 2 0.786716 1.044240 0.516270 11.00000 -1.50000 AFIX 0 C55 1 0.432282 1.055322 0.848931 11.00000 0.06479 0.03578 = 0.03284 -0.01829 -0.02094 0.00522 C56 1 0.321379 1.107233 0.836640 11.00000 0.05198 0.07498 = 0.03546 -0.02498 -0.00891 0.01439 AFIX 33 H56A 2 0.262464 1.082285 0.818111 11.00000 -1.50000 H56B 2 0.352024 1.162940 0.800235 11.00000 -1.50000 H56C 2 0.277386 1.110297 0.883565 11.00000 -1.50000 AFIX 0 C57 1 0.407586 0.966855 0.903999 11.00000 0.13149 0.04469 = 0.03749 -0.01345 -0.00425 0.00190 AFIX 33 H57A 2 0.354576 0.935857 0.887232 11.00000 -1.50000 H57B 2 0.363567 0.965476 0.952612 11.00000 -1.50000 H57C 2 0.488600 0.941860 0.907867 11.00000 -1.50000 AFIX 0 C58 1 0.519251 1.099002 0.880229 11.00000 0.07490 0.09814 = 0.08252 -0.07271 -0.03102 0.01865 AFIX 33 H58A 2 0.471615 1.100158 0.927234 11.00000 -1.50000 H58B 2 0.545589 1.155605 0.844465 11.00000 -1.50000 H58C 2 0.594622 1.068401 0.888445 11.00000 -1.50000 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM XZ116_0m in P-1 REM R1 = 0.0856 for 7561 Fo > 4sig(Fo) and 0.1217 for all 12010 data REM 883 parameters refined using 0 restraints END WGHT 0.1086 6.5266 REM Highest difference peak 1.451, deepest hole -0.536, 1-sigma level 0.076 Q1 1 0.5851 0.5463 0.2867 11.00000 0.05 1.45 Q2 1 0.2980 0.9511 0.7097 11.00000 0.05 1.14 Q3 1 0.0186 1.1340 0.5711 11.00000 0.05 0.91 Q4 1 0.0766 1.1090 0.7783 11.00000 0.05 0.85 Q5 1 0.1917 1.2127 0.5433 11.00000 0.05 0.80 Q6 1 0.1247 1.2346 0.6738 11.00000 0.05 0.74 Q7 1 0.7427 0.5204 0.1054 11.00000 0.05 0.67 Q8 1 0.3089 0.9713 0.8946 11.00000 0.05 0.61 Q9 1 -0.0575 1.1412 0.7107 11.00000 0.05 0.59 Q10 1 0.6604 0.5994 0.2258 11.00000 0.05 0.58 ; #====end data_xz117 _database_code_depnum_ccdc_archive 'CCDC 870173' #TrackingRef '- all-CIFs.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C43.99 H27.98 B Cl1.98 F16 O P' _chemical_formula_weight 988.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.2019(6) _cell_length_b 14.7018(6) _cell_length_c 16.5689(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.1350(10) _cell_angle_gamma 90.00 _cell_volume 4166.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.576 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1990 _exptl_absorpt_coefficient_mu 0.301 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9204 _exptl_absorpt_correction_T_max 0.9394 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36893 _diffrn_reflns_av_R_equivalents 0.0539 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 27.52 _reflns_number_total 9505 _reflns_number_gt 7102 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0469P)^2^+1.9980P] 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 9505 _refine_ls_number_parameters 643 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1155 _refine_ls_wR_factor_gt 0.1041 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 P1 P 0.21850(2) 0.49772(3) 0.28358(3) 0.02182(10) Uani 1 1 d . . . F1 F 0.14065(7) 0.30025(9) 0.59190(8) 0.0442(3) Uani 1 1 d . . . F2 F 0.08393(8) 0.14002(10) 0.54756(9) 0.0548(4) Uani 1 1 d . . . F3 F 0.16037(9) 0.02821(9) 0.45179(9) 0.0621(4) Uani 1 1 d . . . F4 F 0.29847(9) 0.08478(10) 0.40087(9) 0.0617(4) Uani 1 1 d . . . F5 F 0.35692(7) 0.24707(9) 0.44320(8) 0.0468(3) Uani 1 1 d . . . F6 F 0.33003(6) 0.30738(8) 0.71035(7) 0.0393(3) Uani 1 1 d . . . F7 F 0.46634(8) 0.25762(10) 0.78679(8) 0.0536(4) Uani 1 1 d . . . F8 F 0.60022(7) 0.27326(11) 0.71243(9) 0.0598(4) Uani 1 1 d . . . F9 F 0.59202(6) 0.34093(9) 0.55935(8) 0.0468(3) Uani 1 1 d . . . F10 F 0.45811(6) 0.39314(9) 0.48210(7) 0.0394(3) Uani 1 1 d . . . F11 F 0.35833(7) 0.55708(10) 0.66079(9) 0.0561(4) Uani 1 1 d . . . F12 F 0.27991(10) 0.52783(11) 0.74974(8) 0.0683(4) Uani 1 1 d . . . F13 F 0.26997(8) 0.65346(9) 0.68363(7) 0.0504(3) Uani 1 1 d . . . F14 F 0.12086(8) 0.60343(9) 0.64819(8) 0.0518(4) Uani 1 1 d . . . F15 F 0.09551(7) 0.48777(10) 0.56998(9) 0.0515(3) Uani 1 1 d . . . F16 F 0.13432(8) 0.46842(10) 0.69611(9) 0.0603(4) Uani 1 1 d . . . O1 O 0.25067(7) 0.42680(9) 0.60842(7) 0.0282(3) Uani 1 1 d . . . C1 C 0.25410(10) 0.28320(12) 0.52179(11) 0.0270(4) Uani 1 1 d . . . C2 C 0.18407(11) 0.25049(14) 0.54514(11) 0.0314(4) Uani 1 1 d . . . C3 C 0.15274(12) 0.16639(15) 0.52285(12) 0.0374(5) Uani 1 1 d . . . C4 C 0.19119(13) 0.10986(14) 0.47498(13) 0.0420(5) Uani 1 1 d . . . C5 C 0.26055(13) 0.13806(15) 0.44937(13) 0.0412(5) Uani 1 1 d . . . C6 C 0.28935(11) 0.22303(14) 0.47226(12) 0.0340(4) Uani 1 1 d . . . C7 C 0.38476(10) 0.35585(12) 0.59239(11) 0.0252(4) Uani 1 1 d . . . C8 C 0.39353(10) 0.31968(12) 0.67054(11) 0.0277(4) Uani 1 1 d . . . C9 C 0.46349(12) 0.29215(14) 0.71154(12) 0.0357(4) Uani 1 1 d . . . C10 C 0.53062(11) 0.29938(15) 0.67389(14) 0.0392(5) Uani 1 1 d . . . C11 C 0.52605(10) 0.33372(14) 0.59690(13) 0.0340(4) Uani 1 1 d . . . C12 C 0.45504(10) 0.36138(13) 0.55817(11) 0.0287(4) Uani 1 1 d . . . C13 C 0.22994(10) 0.51727(13) 0.60932(11) 0.0277(4) Uani 1 1 d . . . C14 C 0.23284(11) 0.57198(12) 0.52988(11) 0.0273(4) Uani 1 1 d . . . H14A H 0.1884 0.6152 0.5234 0.033 Uiso 1 1 calc R . . H14B H 0.2819 0.6077 0.5334 0.033 Uiso 1 1 calc R . . C15 C 0.22887(10) 0.50930(12) 0.45544(10) 0.0233(4) Uani 1 1 d . . . H15A H 0.1798 0.4724 0.4521 0.028 Uiso 1 1 calc R . . C16 C 0.29958(10) 0.44648(12) 0.46773(11) 0.0258(4) Uani 1 1 d . . . H16A H 0.3479 0.4835 0.4742 0.031 Uiso 1 1 calc R . . H16B H 0.3011 0.4077 0.4191 0.031 Uiso 1 1 calc R . . C17 C 0.28425(13) 0.56406(15) 0.67660(12) 0.0404(5) Uani 1 1 d . . . C18 C 0.14525(12) 0.51888(15) 0.63163(13) 0.0392(5) Uani 1 1 d . . . C19 C 0.22932(10) 0.56814(12) 0.37740(10) 0.0232(4) Uani 1 1 d . . . H19A H 0.2830 0.5949 0.3802 0.028 Uiso 1 1 calc R . . C20 C 0.17380(10) 0.64865(12) 0.37030(10) 0.0245(4) Uani 1 1 d . . . C21 C 0.20359(13) 0.73468(14) 0.35833(13) 0.0374(5) Uani 1 1 d . . . H21A H 0.2579 0.7420 0.3545 0.045 Uiso 1 1 calc R . . C22 C 0.15483(16) 0.81034(15) 0.35185(14) 0.0496(6) Uani 1 1 d . . . H22A H 0.1759 0.8690 0.3439 0.060 Uiso 1 1 calc R . . C23 C 0.07651(15) 0.80001(17) 0.35696(13) 0.0479(6) Uani 1 1 d . . . H23A H 0.0430 0.8515 0.3516 0.057 Uiso 1 1 calc R . . C24 C 0.04590(12) 0.71545(17) 0.36977(14) 0.0452(6) Uani 1 1 d . . . H24A H -0.0085 0.7089 0.3737 0.054 Uiso 1 1 calc R . . C25 C 0.09432(11) 0.63955(15) 0.37697(12) 0.0348(4) Uani 1 1 d . . . H25A H 0.0731 0.5814 0.3865 0.042 Uiso 1 1 calc R . . C26 C 0.16047(10) 0.55649(12) 0.20305(10) 0.0258(4) Uani 1 1 d . . . C27 C 0.19013(13) 0.63572(14) 0.17246(12) 0.0372(5) Uani 1 1 d . . . H27A H 0.2389 0.6593 0.1956 0.045 Uiso 1 1 calc R . . C28 C 0.14843(15) 0.68022(15) 0.10822(13) 0.0459(5) Uani 1 1 d . . . H28A H 0.1689 0.7342 0.0871 0.055 Uiso 1 1 calc R . . C29 C 0.07747(14) 0.64671(15) 0.07469(13) 0.0429(5) Uani 1 1 d . . . H29A H 0.0491 0.6778 0.0307 0.051 Uiso 1 1 calc R . . C30 C 0.04759(12) 0.56874(16) 0.10455(12) 0.0403(5) Uani 1 1 d . . . H30A H -0.0014 0.5459 0.0812 0.048 Uiso 1 1 calc R . . C31 C 0.08880(11) 0.52309(14) 0.16880(12) 0.0327(4) Uani 1 1 d . . . H31A H 0.0681 0.4690 0.1894 0.039 Uiso 1 1 calc R . . C32 C 0.31221(10) 0.47940(12) 0.24641(11) 0.0256(4) Uani 1 1 d . . . C33 C 0.31315(12) 0.45368(15) 0.16531(12) 0.0377(5) Uani 1 1 d . . . H33A H 0.2654 0.4477 0.1311 0.045 Uiso 1 1 calc R . . C34 C 0.38345(13) 0.43687(17) 0.13489(14) 0.0461(6) Uani 1 1 d . . . H34A H 0.3838 0.4190 0.0798 0.055 Uiso 1 1 calc R . . C35 C 0.45296(12) 0.44572(15) 0.18359(14) 0.0417(5) Uani 1 1 d . . . H35A H 0.5010 0.4339 0.1622 0.050 Uiso 1 1 calc R . . C36 C 0.45287(11) 0.47184(15) 0.26357(14) 0.0396(5) Uani 1 1 d . . . H36A H 0.5009 0.4786 0.2970 0.048 Uiso 1 1 calc R . . C37 C 0.38270(10) 0.48836(14) 0.29534(12) 0.0315(4) Uani 1 1 d . . . H37A H 0.3828 0.5058 0.3506 0.038 Uiso 1 1 calc R . . C38 C 0.17275(10) 0.38970(12) 0.29811(10) 0.0239(4) Uani 1 1 d . . . C39 C 0.20917(11) 0.31038(13) 0.27652(11) 0.0287(4) Uani 1 1 d . . . H39A H 0.2596 0.3132 0.2582 0.034 Uiso 1 1 calc R . . C40 C 0.17235(11) 0.22716(13) 0.28166(12) 0.0326(4) Uani 1 1 d . . . H40A H 0.1973 0.1731 0.2664 0.039 Uiso 1 1 calc R . . C41 C 0.09940(11) 0.22272(14) 0.30896(12) 0.0342(4) Uani 1 1 d . . . H41A H 0.0740 0.1656 0.3121 0.041 Uiso 1 1 calc R . . C42 C 0.06315(11) 0.30138(14) 0.33186(13) 0.0355(4) Uani 1 1 d . . . H42A H 0.0134 0.2978 0.3515 0.043 Uiso 1 1 calc R . . C43 C 0.09887(10) 0.38483(13) 0.32627(12) 0.0300(4) Uani 1 1 d . . . H43A H 0.0735 0.4387 0.3414 0.036 Uiso 1 1 calc R . . B1 B 0.29641(11) 0.38217(14) 0.54745(12) 0.0247(4) Uani 1 1 d . . . Cl1 Cl 0.5126(3) 0.1199(4) 0.4677(4) 0.0819(13) Uani 0.450(17) 1 d P A 1 Cl2 Cl 0.6775(3) 0.1464(8) 0.4915(6) 0.133(3) Uani 0.450(17) 1 d P A 1 C44 C 0.5916(10) 0.1666(11) 0.4309(7) 0.065(5) Uani 0.450(17) 1 d P A 1 H44A H 0.5836 0.2331 0.4255 0.077 Uiso 0.450(17) 1 calc PR A 1 H44B H 0.5960 0.1418 0.3761 0.077 Uiso 0.450(17) 1 calc PR A 1 Cl1A Cl 0.6324(2) 0.2165(2) 0.4089(2) 0.0830(12) Uani 0.315(3) 1 d P B 2 Cl2A Cl 0.6012(3) 0.1077(2) 0.5432(2) 0.1188(19) Uani 0.315(3) 1 d P B 2 C44A C 0.5580(8) 0.1595(11) 0.4473(13) 0.067(5) Uani 0.315(3) 1 d P B 2 H44C H 0.5364 0.1120 0.4089 0.081 Uiso 0.315(3) 1 calc PR B 2 H44D H 0.5154 0.2019 0.4575 0.081 Uiso 0.315(3) 1 calc PR B 2 Cl1B Cl 0.5253(11) 0.1154(8) 0.4951(17) 0.107(5) Uani 0.224(17) 1 d P C 3 Cl2B Cl 0.6795(4) 0.1668(7) 0.4747(8) 0.086(3) Uani 0.224(17) 1 d P C 3 C44B C 0.589(2) 0.1713(19) 0.423(2) 0.093(17) Uani 0.224(17) 1 d P C 3 H44E H 0.5870 0.1373 0.3709 0.111 Uiso 0.224(17) 1 calc PR C 3 H44F H 0.5725 0.2349 0.4110 0.111 Uiso 0.224(17) 1 calc PR C 3 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 P1 0.0206(2) 0.0225(2) 0.0222(2) 0.00005(17) 0.00155(16) -0.00085(17) F1 0.0328(6) 0.0506(8) 0.0515(7) -0.0048(6) 0.0140(6) -0.0078(5) F2 0.0448(7) 0.0554(9) 0.0627(9) 0.0092(7) -0.0006(6) -0.0242(6) F3 0.0756(10) 0.0350(7) 0.0715(10) -0.0058(7) -0.0125(8) -0.0176(7) F4 0.0746(10) 0.0419(8) 0.0682(10) -0.0240(7) 0.0062(8) 0.0043(7) F5 0.0416(7) 0.0437(7) 0.0576(8) -0.0171(6) 0.0175(6) -0.0016(6) F6 0.0298(6) 0.0475(7) 0.0417(7) 0.0176(5) 0.0090(5) 0.0015(5) F7 0.0471(7) 0.0680(9) 0.0434(7) 0.0230(7) -0.0064(6) 0.0069(7) F8 0.0272(6) 0.0778(10) 0.0706(9) 0.0111(8) -0.0122(6) 0.0126(6) F9 0.0227(5) 0.0557(8) 0.0634(8) -0.0022(7) 0.0118(5) 0.0002(5) F10 0.0329(6) 0.0509(7) 0.0359(6) 0.0068(5) 0.0110(5) 0.0040(5) F11 0.0363(7) 0.0570(9) 0.0699(9) -0.0197(7) -0.0179(6) 0.0074(6) F12 0.1080(13) 0.0659(10) 0.0270(7) 0.0019(6) -0.0115(7) 0.0180(9) F13 0.0674(9) 0.0385(7) 0.0420(7) -0.0156(6) -0.0099(6) 0.0122(6) F14 0.0524(8) 0.0435(8) 0.0635(9) 0.0074(6) 0.0252(7) 0.0251(6) F15 0.0269(6) 0.0575(9) 0.0699(9) 0.0088(7) 0.0044(6) 0.0019(6) F16 0.0646(9) 0.0601(9) 0.0632(9) 0.0279(7) 0.0396(7) 0.0268(7) O1 0.0298(6) 0.0268(7) 0.0286(7) 0.0027(5) 0.0055(5) 0.0076(5) C1 0.0270(9) 0.0269(9) 0.0257(9) 0.0033(7) -0.0042(7) 0.0003(7) C2 0.0293(9) 0.0343(11) 0.0293(10) 0.0051(8) -0.0037(8) -0.0015(8) C3 0.0349(10) 0.0380(11) 0.0367(11) 0.0117(9) -0.0087(9) -0.0104(9) C4 0.0504(13) 0.0297(11) 0.0417(12) 0.0054(9) -0.0151(10) -0.0096(9) C5 0.0517(13) 0.0320(11) 0.0379(11) -0.0064(9) -0.0045(10) 0.0056(10) C6 0.0326(10) 0.0328(11) 0.0357(11) -0.0015(8) 0.0004(8) -0.0006(8) C7 0.0240(8) 0.0203(8) 0.0313(9) -0.0008(7) 0.0022(7) -0.0002(7) C8 0.0236(8) 0.0250(9) 0.0346(10) 0.0031(8) 0.0041(7) -0.0002(7) C9 0.0350(10) 0.0342(11) 0.0361(11) 0.0061(8) -0.0044(8) 0.0015(8) C10 0.0223(9) 0.0400(12) 0.0530(13) -0.0006(10) -0.0063(9) 0.0033(8) C11 0.0214(9) 0.0338(11) 0.0471(12) -0.0044(9) 0.0053(8) -0.0018(8) C12 0.0276(9) 0.0268(9) 0.0322(10) -0.0015(8) 0.0047(8) -0.0007(7) C13 0.0285(9) 0.0288(10) 0.0260(9) -0.0011(7) 0.0032(7) 0.0079(7) C14 0.0294(9) 0.0254(9) 0.0265(9) -0.0027(7) 0.0006(7) 0.0026(7) C15 0.0234(8) 0.0232(9) 0.0232(8) -0.0004(7) 0.0018(7) 0.0006(7) C16 0.0249(8) 0.0268(9) 0.0257(9) -0.0014(7) 0.0021(7) 0.0026(7) C17 0.0493(13) 0.0389(12) 0.0308(11) -0.0038(9) -0.0051(9) 0.0143(10) C18 0.0393(11) 0.0383(12) 0.0424(12) 0.0105(9) 0.0146(10) 0.0140(9) C19 0.0202(8) 0.0256(9) 0.0235(8) -0.0015(7) 0.0014(7) -0.0028(7) C20 0.0275(9) 0.0277(9) 0.0183(8) -0.0009(7) 0.0021(7) 0.0037(7) C21 0.0428(11) 0.0308(11) 0.0410(11) 0.0012(9) 0.0155(9) 0.0024(9) C22 0.0743(17) 0.0301(12) 0.0480(13) 0.0073(10) 0.0222(12) 0.0130(11) C23 0.0609(15) 0.0447(14) 0.0377(12) 0.0031(10) 0.0038(11) 0.0276(12) C24 0.0318(11) 0.0586(15) 0.0439(12) -0.0103(11) -0.0017(9) 0.0151(10) C25 0.0276(9) 0.0380(11) 0.0383(11) -0.0060(9) 0.0012(8) 0.0028(8) C26 0.0301(9) 0.0246(9) 0.0222(9) -0.0011(7) 0.0006(7) 0.0027(7) C27 0.0476(12) 0.0306(11) 0.0318(10) 0.0036(8) -0.0036(9) -0.0060(9) C28 0.0685(15) 0.0311(11) 0.0368(12) 0.0086(9) -0.0009(11) -0.0001(10) C29 0.0575(14) 0.0397(12) 0.0295(10) 0.0029(9) -0.0045(10) 0.0167(10) C30 0.0357(11) 0.0477(13) 0.0352(11) -0.0013(9) -0.0068(9) 0.0090(9) C31 0.0306(9) 0.0345(11) 0.0319(10) 0.0025(8) -0.0012(8) 0.0024(8) C32 0.0229(8) 0.0262(9) 0.0284(9) -0.0001(7) 0.0058(7) -0.0030(7) C33 0.0309(10) 0.0502(13) 0.0330(11) -0.0099(9) 0.0075(8) -0.0080(9) C34 0.0423(12) 0.0586(15) 0.0397(12) -0.0160(11) 0.0161(10) -0.0086(11) C35 0.0319(10) 0.0449(13) 0.0513(13) -0.0039(10) 0.0181(10) -0.0017(9) C36 0.0249(9) 0.0483(13) 0.0458(12) 0.0022(10) 0.0040(9) 0.0014(9) C37 0.0278(9) 0.0373(11) 0.0298(10) -0.0001(8) 0.0037(8) 0.0006(8) C38 0.0234(8) 0.0247(9) 0.0235(9) 0.0001(7) 0.0010(7) -0.0012(7) C39 0.0265(9) 0.0282(10) 0.0317(10) -0.0020(8) 0.0045(8) -0.0013(7) C40 0.0342(10) 0.0263(10) 0.0369(11) -0.0020(8) 0.0022(8) -0.0018(8) C41 0.0365(10) 0.0283(10) 0.0369(11) 0.0032(8) 0.0000(8) -0.0104(8) C42 0.0272(9) 0.0389(11) 0.0413(11) 0.0022(9) 0.0075(8) -0.0060(8) C43 0.0265(9) 0.0282(10) 0.0358(10) -0.0001(8) 0.0060(8) -0.0002(7) B1 0.0224(9) 0.0253(10) 0.0265(10) 0.0011(8) 0.0024(8) 0.0024(8) Cl1 0.0608(16) 0.102(2) 0.088(3) -0.0081(16) 0.0312(17) 0.020(2) Cl2 0.085(3) 0.207(6) 0.100(3) -0.063(3) -0.031(3) 0.034(3) C44 0.082(11) 0.081(8) 0.037(4) 0.001(4) 0.033(6) -0.009(7) Cl1A 0.081(2) 0.116(3) 0.0560(16) 0.0002(18) 0.0277(16) -0.0197(19) Cl2A 0.196(5) 0.082(2) 0.087(2) 0.0224(17) 0.055(3) -0.010(3) C44A 0.062(8) 0.076(9) 0.073(10) -0.023(7) 0.046(7) -0.021(6) Cl1B 0.107(8) 0.097(5) 0.133(13) -0.028(5) 0.081(8) -0.047(5) Cl2B 0.041(3) 0.092(5) 0.131(8) -0.063(4) 0.040(5) -0.017(3) C44B 0.08(2) 0.033(10) 0.15(3) -0.004(13) -0.10(2) -0.013(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C26 1.7996(18) . ? P1 C38 1.8000(18) . ? P1 C32 1.8062(17) . ? P1 C19 1.8605(17) . ? F1 C2 1.348(2) . ? F2 C3 1.350(2) . ? F3 C4 1.351(2) . ? F4 C5 1.341(2) . ? F5 C6 1.352(2) . ? F6 C8 1.347(2) . ? F7 C9 1.342(2) . ? F8 C10 1.351(2) . ? F9 C11 1.355(2) . ? F10 C12 1.351(2) . ? F11 C17 1.332(3) . ? F12 C17 1.333(3) . ? F13 C17 1.344(2) . ? F14 C18 1.349(2) . ? F15 C18 1.341(3) . ? F16 C18 1.331(2) . ? O1 C13 1.378(2) . ? O1 B1 1.497(2) . ? C1 C6 1.389(3) . ? C1 C2 1.390(3) . ? C1 B1 1.662(3) . ? C2 C3 1.383(3) . ? C3 C4 1.367(3) . ? C4 C5 1.372(3) . ? C5 C6 1.382(3) . ? C7 C12 1.391(2) . ? C7 C8 1.393(3) . ? C7 B1 1.665(3) . ? C8 C9 1.378(3) . ? C9 C10 1.374(3) . ? C10 C11 1.366(3) . ? C11 C12 1.379(3) . ? C13 C17 1.538(3) . ? C13 C18 1.541(3) . ? C13 C14 1.548(3) . ? C14 C15 1.535(2) . ? C15 C16 1.523(2) . ? C15 C19 1.556(2) . ? C16 B1 1.630(3) . ? C19 C20 1.518(2) . ? C20 C21 1.387(3) . ? C20 C25 1.390(3) . ? C21 C22 1.390(3) . ? C22 C23 1.367(4) . ? C23 C24 1.375(3) . ? C24 C25 1.390(3) . ? C26 C27 1.389(3) . ? C26 C31 1.391(3) . ? C27 C28 1.383(3) . ? C28 C29 1.377(3) . ? C29 C30 1.370(3) . ? C30 C31 1.387(3) . ? C32 C37 1.391(2) . ? C32 C33 1.398(3) . ? C33 C34 1.381(3) . ? C34 C35 1.376(3) . ? C35 C36 1.380(3) . ? C36 C37 1.389(3) . ? C38 C39 1.389(3) . ? C38 C43 1.402(2) . ? C39 C40 1.384(3) . ? C40 C41 1.380(3) . ? C41 C42 1.386(3) . ? C42 C43 1.380(3) . ? Cl1 C44 1.692(16) . ? Cl2 C44 1.722(16) . ? Cl1A C44A 1.708(13) . ? Cl2A C44A 1.845(19) . ? Cl1B C44B 1.89(5) . ? Cl2B C44B 1.70(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 C26 P1 C38 107.88(8) . . ? C26 P1 C32 105.27(8) . . ? C38 P1 C32 109.45(8) . . ? C26 P1 C19 110.51(8) . . ? C38 P1 C19 112.67(8) . . ? C32 P1 C19 110.77(8) . . ? C13 O1 B1 125.88(14) . . ? C6 C1 C2 112.96(17) . . ? C6 C1 B1 120.12(16) . . ? C2 C1 B1 126.92(17) . . ? F1 C2 C3 114.50(17) . . ? F1 C2 C1 121.48(17) . . ? C3 C2 C1 124.02(19) . . ? F2 C3 C4 119.71(19) . . ? F2 C3 C2 120.3(2) . . ? C4 C3 C2 119.97(19) . . ? F3 C4 C3 120.4(2) . . ? F3 C4 C5 120.5(2) . . ? C3 C4 C5 119.09(19) . . ? F4 C5 C4 120.2(2) . . ? F4 C5 C6 120.6(2) . . ? C4 C5 C6 119.1(2) . . ? F5 C6 C5 115.80(18) . . ? F5 C6 C1 119.34(17) . . ? C5 C6 C1 124.85(19) . . ? C12 C7 C8 112.87(16) . . ? C12 C7 B1 126.55(16) . . ? C8 C7 B1 120.49(15) . . ? F6 C8 C9 115.48(16) . . ? F6 C8 C7 119.57(15) . . ? C9 C8 C7 124.92(17) . . ? F7 C9 C10 120.13(18) . . ? F7 C9 C8 120.82(18) . . ? C10 C9 C8 119.04(18) . . ? F8 C10 C11 120.40(19) . . ? F8 C10 C9 120.6(2) . . ? C11 C10 C9 119.03(18) . . ? F9 C11 C10 119.34(17) . . ? F9 C11 C12 120.46(18) . . ? C10 C11 C12 120.20(18) . . ? F10 C12 C11 114.52(16) . . ? F10 C12 C7 121.53(16) . . ? C11 C12 C7 123.94(18) . . ? O1 C13 C17 107.57(15) . . ? O1 C13 C18 105.67(15) . . ? C17 C13 C18 109.63(16) . . ? O1 C13 C14 117.42(14) . . ? C17 C13 C14 108.15(16) . . ? C18 C13 C14 108.25(15) . . ? C15 C14 C13 111.63(15) . . ? C16 C15 C14 106.87(14) . . ? C16 C15 C19 111.91(14) . . ? C14 C15 C19 109.27(14) . . ? C15 C16 B1 111.39(14) . . ? F11 C17 F12 107.20(17) . . ? F11 C17 F13 106.26(19) . . ? F12 C17 F13 106.47(17) . . ? F11 C17 C13 110.04(16) . . ? F12 C17 C13 113.04(19) . . ? F13 C17 C13 113.42(16) . . ? F16 C18 F15 106.74(18) . . ? F16 C18 F14 106.06(16) . . ? F15 C18 F14 106.39(16) . . ? F16 C18 C13 113.73(16) . . ? F15 C18 C13 110.78(16) . . ? F14 C18 C13 112.67(17) . . ? C20 C19 C15 116.04(14) . . ? C20 C19 P1 111.30(11) . . ? C15 C19 P1 112.08(12) . . ? C21 C20 C25 118.73(17) . . ? C21 C20 C19 118.90(16) . . ? C25 C20 C19 122.35(17) . . ? C20 C21 C22 120.8(2) . . ? C23 C22 C21 119.8(2) . . ? C22 C23 C24 120.4(2) . . ? C23 C24 C25 120.2(2) . . ? C20 C25 C24 120.1(2) . . ? C27 C26 C31 119.43(17) . . ? C27 C26 P1 118.49(14) . . ? C31 C26 P1 122.03(14) . . ? C28 C27 C26 119.81(19) . . ? C29 C28 C27 120.4(2) . . ? C30 C29 C28 120.27(19) . . ? C29 C30 C31 120.1(2) . . ? C30 C31 C26 120.03(19) . . ? C37 C32 C33 119.15(16) . . ? C37 C32 P1 122.78(14) . . ? C33 C32 P1 118.07(14) . . ? C34 C33 C32 119.99(19) . . ? C35 C34 C33 120.6(2) . . ? C34 C35 C36 119.97(19) . . ? C35 C36 C37 120.20(19) . . ? C36 C37 C32 120.09(18) . . ? C39 C38 C43 119.53(16) . . ? C39 C38 P1 119.40(13) . . ? C43 C38 P1 120.96(14) . . ? C40 C39 C38 120.29(17) . . ? C41 C40 C39 119.99(18) . . ? C40 C41 C42 120.11(18) . . ? C43 C42 C41 120.46(17) . . ? C42 C43 C38 119.59(17) . . ? O1 B1 C16 110.99(14) . . ? O1 B1 C1 108.00(14) . . ? C16 B1 C1 110.63(15) . . ? O1 B1 C7 108.70(14) . . ? C16 B1 C7 112.91(14) . . ? C1 B1 C7 105.36(14) . . ? Cl1 C44 Cl2 113.1(8) . . ? Cl1A C44A Cl2A 105.9(8) . . ? Cl2B C44B Cl1B 102.8(19) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.338 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.050 _vrf_PLAT214_ALERT_2_Atom_C44B ; PROBLEM:ADP max/min Ratio 8.9 prola RESPONSE: This atoms is part of a disordered group. ; #===end data_xz115_0m _database_code_depnum_ccdc_archive 'CCDC 870174' #TrackingRef '- all-CIFs.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H28 B F16 N O' _chemical_formula_weight 709.32 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.1411(7) _cell_length_b 17.8797(11) _cell_length_c 14.7969(10) _cell_angle_alpha 90.00 _cell_angle_beta 98.591(4) _cell_angle_gamma 90.00 _cell_volume 2914.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.617 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.168 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9640 _exptl_absorpt_correction_T_max 0.9802 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 45488 _diffrn_reflns_av_R_equivalents 0.0541 _diffrn_reflns_av_sigmaI/netI 0.0559 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 33.66 _reflns_number_total 11532 _reflns_number_gt 6876 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0455P)^2^+0.4424P] 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 11532 _refine_ls_number_parameters 433 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0969 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1177 _refine_ls_wR_factor_gt 0.0979 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _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 0.19673(8) 0.42310(5) 0.75376(6) 0.0333(2) Uani 1 1 d . . . F2 F 0.18273(9) 0.46340(6) 0.92492(6) 0.0466(3) Uani 1 1 d . . . F3 F -0.00346(10) 0.41286(6) 1.01022(6) 0.0468(3) Uani 1 1 d . . . F4 F -0.17441(9) 0.32116(5) 0.91917(6) 0.0382(2) Uani 1 1 d . . . F5 F -0.16700(7) 0.28254(5) 0.74750(6) 0.02892(18) Uani 1 1 d . . . F6 F 0.28736(8) 0.36650(5) 0.58159(6) 0.0324(2) Uani 1 1 d . . . F7 F 0.47723(8) 0.27694(6) 0.60629(7) 0.0456(3) Uani 1 1 d . . . F8 F 0.46492(9) 0.14029(6) 0.68761(7) 0.0493(3) Uani 1 1 d . . . F9 F 0.25078(9) 0.09428(5) 0.73652(6) 0.0400(2) Uani 1 1 d . . . F10 F 0.05690(7) 0.18268(4) 0.71256(6) 0.02772(18) Uani 1 1 d . . . F11 F -0.30142(8) 0.32917(5) 0.54426(7) 0.0399(2) Uani 1 1 d . . . F12 F -0.28851(8) 0.20934(5) 0.54350(7) 0.0391(2) Uani 1 1 d . . . F13 F -0.32173(8) 0.26994(6) 0.41659(7) 0.0423(2) Uani 1 1 d . . . F14 F -0.07842(10) 0.14823(5) 0.51166(7) 0.0410(2) Uani 1 1 d . . . F15 F -0.13121(9) 0.19248(5) 0.37676(6) 0.0424(2) Uani 1 1 d . . . F16 F 0.04523(8) 0.21670(5) 0.45096(6) 0.0373(2) Uani 1 1 d . . . O1 O -0.07170(8) 0.28264(5) 0.59316(6) 0.01978(18) Uani 1 1 d . . . N1 N 0.95120(10) 0.03905(6) 0.78007(7) 0.0195(2) Uani 1 1 d . . . C1 C 0.01465(12) 0.35186(7) 0.73941(8) 0.0200(2) Uani 1 1 d . . . C2 C 0.10013(13) 0.39767(8) 0.79103(9) 0.0248(3) Uani 1 1 d . . . C3 C 0.09629(14) 0.41907(8) 0.88037(10) 0.0303(3) Uani 1 1 d . . . C4 C 0.00294(15) 0.39344(8) 0.92338(9) 0.0316(3) Uani 1 1 d . . . C5 C -0.08364(13) 0.34715(8) 0.87668(9) 0.0272(3) Uani 1 1 d . . . C6 C -0.07694(12) 0.32782(7) 0.78682(9) 0.0220(3) Uani 1 1 d . . . C7 C 0.15894(11) 0.27933(7) 0.64319(8) 0.0185(2) Uani 1 1 d . . . C8 C 0.27061(12) 0.29876(8) 0.61935(9) 0.0229(3) Uani 1 1 d . . . C9 C 0.37257(12) 0.25347(9) 0.63199(9) 0.0296(3) Uani 1 1 d . . . C10 C 0.36664(13) 0.18432(9) 0.67148(10) 0.0315(3) Uani 1 1 d . . . C11 C 0.25814(14) 0.16174(8) 0.69681(9) 0.0268(3) Uani 1 1 d . . . C12 C 0.15923(12) 0.20885(7) 0.68242(8) 0.0210(2) Uani 1 1 d . . . C13 C -0.12075(12) 0.27974(7) 0.50184(8) 0.0201(2) Uani 1 1 d . . . C14 C -0.09998(14) 0.34803(8) 0.44205(9) 0.0275(3) Uani 1 1 d . . . H14A H -0.1055 0.3316 0.3777 0.033 Uiso 1 1 calc R . . H14B H -0.1654 0.3849 0.4454 0.033 Uiso 1 1 calc R . . C15 C 0.02193(14) 0.38585(8) 0.47057(9) 0.0279(3) Uani 1 1 d . . . H15A H 0.0272 0.4316 0.4337 0.034 Uiso 1 1 calc R . . H15B H 0.0883 0.3517 0.4598 0.034 Uiso 1 1 calc R . . C16 C 0.03517(13) 0.40613(7) 0.57195(9) 0.0239(3) Uani 1 1 d . . . H16A H -0.0318 0.4398 0.5826 0.029 Uiso 1 1 calc R . . H16B H 0.1128 0.4328 0.5903 0.029 Uiso 1 1 calc R . . C17 C -0.25858(13) 0.27115(8) 0.50157(10) 0.0284(3) Uani 1 1 d . . . C18 C -0.07206(13) 0.20890(8) 0.46018(9) 0.0263(3) Uani 1 1 d . . . C19 C 0.85264(12) 0.06744(7) 0.83677(8) 0.0204(2) Uani 1 1 d . . . C20 C 0.74293(13) 0.09264(8) 0.76905(9) 0.0256(3) Uani 1 1 d . . . H20A H 0.6769 0.1073 0.8034 0.031 Uiso 1 1 calc R . . H20B H 0.7656 0.1373 0.7359 0.031 Uiso 1 1 calc R . . C21 C 0.69588(13) 0.03265(8) 0.69991(10) 0.0287(3) Uani 1 1 d . . . H21A H 0.6724 -0.0124 0.7320 0.034 Uiso 1 1 calc R . . H21B H 0.6234 0.0512 0.6592 0.034 Uiso 1 1 calc R . . C22 C 0.79527(13) 0.01315(8) 0.64407(9) 0.0249(3) Uani 1 1 d . . . H22A H 0.8147 0.0584 0.6105 0.030 Uiso 1 1 calc R . . H22B H 0.7636 -0.0250 0.5981 0.030 Uiso 1 1 calc R . . C23 C 0.91253(12) -0.01646(7) 0.69932(8) 0.0211(2) Uani 1 1 d . . . C24 C 1.06516(13) 0.01429(9) 0.83974(10) 0.0323(3) Uani 1 1 d . . . H24A H 1.0977 0.0557 0.8793 0.049 Uiso 1 1 calc R . . H24B H 1.1253 -0.0010 0.8014 0.049 Uiso 1 1 calc R . . H24C H 1.0469 -0.0280 0.8775 0.049 Uiso 1 1 calc R . . C25 C 0.81702(14) 0.00772(8) 0.90170(9) 0.0277(3) Uani 1 1 d . . . H25A H 0.7646 0.0300 0.9420 0.042 Uiso 1 1 calc R . . H25B H 0.8903 -0.0124 0.9385 0.042 Uiso 1 1 calc R . . H25C H 0.7733 -0.0327 0.8662 0.042 Uiso 1 1 calc R . . C26 C 0.90693(14) 0.13509(8) 0.89145(9) 0.0294(3) Uani 1 1 d . . . H26A H 0.8420 0.1633 0.9140 0.044 Uiso 1 1 calc R . . H26B H 0.9479 0.1673 0.8520 0.044 Uiso 1 1 calc R . . H26C H 0.9657 0.1180 0.9433 0.044 Uiso 1 1 calc R . . C27 C 0.89894(15) -0.09574(8) 0.73407(10) 0.0306(3) Uani 1 1 d . . . H27A H 0.8808 -0.1299 0.6820 0.046 Uiso 1 1 calc R . . H27B H 0.8325 -0.0972 0.7707 0.046 Uiso 1 1 calc R . . H27C H 0.9747 -0.1111 0.7719 0.046 Uiso 1 1 calc R . . C28 C 1.01286(14) -0.01384(9) 0.63855(10) 0.0308(3) Uani 1 1 d . . . H28A H 0.9841 -0.0383 0.5800 0.046 Uiso 1 1 calc R . . H28B H 1.0850 -0.0399 0.6692 0.046 Uiso 1 1 calc R . . H28C H 1.0334 0.0384 0.6277 0.046 Uiso 1 1 calc R . . B1 B 0.03215(13) 0.33143(8) 0.63281(9) 0.0185(3) Uani 1 1 d . . . HN1 H 0.9734(14) 0.0792(9) 0.7537(11) 0.027(4) 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 0.0249(4) 0.0366(5) 0.0383(5) -0.0099(4) 0.0044(4) -0.0099(4) F2 0.0448(6) 0.0521(6) 0.0381(5) -0.0216(5) -0.0095(4) -0.0042(5) F3 0.0630(7) 0.0570(6) 0.0201(4) -0.0088(4) 0.0051(4) 0.0146(5) F4 0.0432(6) 0.0449(5) 0.0309(4) 0.0065(4) 0.0197(4) 0.0077(4) F5 0.0256(4) 0.0317(4) 0.0313(4) -0.0023(3) 0.0102(3) -0.0066(3) F6 0.0267(4) 0.0351(5) 0.0376(5) 0.0045(4) 0.0117(4) -0.0091(4) F7 0.0181(4) 0.0728(7) 0.0487(6) -0.0071(5) 0.0146(4) -0.0016(4) F8 0.0318(5) 0.0638(7) 0.0502(6) -0.0081(5) -0.0007(4) 0.0294(5) F9 0.0487(6) 0.0243(4) 0.0438(5) 0.0043(4) -0.0035(4) 0.0108(4) F10 0.0261(4) 0.0229(4) 0.0356(4) 0.0066(3) 0.0093(3) -0.0016(3) F11 0.0222(5) 0.0406(5) 0.0573(6) -0.0152(4) 0.0071(4) 0.0071(4) F12 0.0266(5) 0.0376(5) 0.0532(6) -0.0002(4) 0.0062(4) -0.0109(4) F13 0.0276(5) 0.0504(6) 0.0428(5) -0.0075(4) -0.0141(4) 0.0014(4) F14 0.0622(7) 0.0203(4) 0.0436(5) 0.0013(4) 0.0179(5) 0.0088(4) F15 0.0510(6) 0.0427(5) 0.0306(4) -0.0167(4) -0.0033(4) 0.0060(5) F16 0.0307(5) 0.0422(5) 0.0417(5) -0.0087(4) 0.0138(4) 0.0086(4) O1 0.0184(4) 0.0219(4) 0.0187(4) -0.0011(3) 0.0019(3) -0.0030(3) N1 0.0192(5) 0.0200(5) 0.0192(5) 0.0003(4) 0.0026(4) -0.0005(4) C1 0.0195(6) 0.0188(6) 0.0214(5) -0.0020(4) 0.0026(5) 0.0039(5) C2 0.0221(7) 0.0249(6) 0.0268(6) -0.0050(5) 0.0015(5) 0.0019(5) C3 0.0305(8) 0.0307(7) 0.0266(6) -0.0088(6) -0.0061(6) 0.0058(6) C4 0.0404(9) 0.0347(8) 0.0189(6) -0.0041(6) 0.0013(6) 0.0145(7) C5 0.0299(8) 0.0294(7) 0.0240(6) 0.0044(5) 0.0096(6) 0.0109(6) C6 0.0219(6) 0.0208(6) 0.0232(6) 0.0001(5) 0.0028(5) 0.0037(5) C7 0.0179(6) 0.0208(6) 0.0172(5) -0.0026(4) 0.0040(4) -0.0003(5) C8 0.0203(6) 0.0284(7) 0.0209(6) -0.0025(5) 0.0056(5) -0.0025(5) C9 0.0166(7) 0.0475(9) 0.0258(6) -0.0081(6) 0.0061(5) 0.0000(6) C10 0.0228(7) 0.0418(8) 0.0282(7) -0.0087(6) -0.0014(6) 0.0155(6) C11 0.0322(8) 0.0231(6) 0.0238(6) -0.0014(5) -0.0002(5) 0.0077(5) C12 0.0194(6) 0.0219(6) 0.0218(5) -0.0020(5) 0.0036(5) 0.0007(5) C13 0.0186(6) 0.0202(6) 0.0208(5) -0.0016(5) 0.0009(5) 0.0014(5) C14 0.0314(8) 0.0250(6) 0.0246(6) 0.0045(5) -0.0012(5) 0.0020(6) C15 0.0329(8) 0.0239(6) 0.0273(6) 0.0077(5) 0.0053(6) -0.0022(6) C16 0.0238(7) 0.0183(6) 0.0297(6) 0.0007(5) 0.0041(5) -0.0014(5) C17 0.0231(7) 0.0268(7) 0.0338(7) -0.0067(6) -0.0011(6) 0.0009(5) C18 0.0294(7) 0.0258(7) 0.0237(6) -0.0029(5) 0.0043(5) 0.0028(5) C19 0.0211(6) 0.0209(6) 0.0199(5) -0.0009(4) 0.0053(5) 0.0002(5) C20 0.0235(7) 0.0249(6) 0.0282(6) -0.0027(5) 0.0032(5) 0.0066(5) C21 0.0195(7) 0.0320(7) 0.0323(7) -0.0048(6) -0.0040(5) 0.0051(5) C22 0.0269(7) 0.0260(6) 0.0203(6) -0.0016(5) -0.0018(5) 0.0029(5) C23 0.0232(7) 0.0182(6) 0.0216(6) -0.0030(4) 0.0026(5) 0.0017(5) C24 0.0202(7) 0.0462(9) 0.0288(7) -0.0009(6) -0.0025(5) 0.0054(6) C25 0.0311(8) 0.0296(7) 0.0239(6) 0.0021(5) 0.0089(5) -0.0029(6) C26 0.0363(8) 0.0274(7) 0.0253(6) -0.0070(5) 0.0068(6) -0.0054(6) C27 0.0354(8) 0.0199(6) 0.0363(7) 0.0001(6) 0.0044(6) 0.0033(6) C28 0.0310(8) 0.0348(8) 0.0284(7) -0.0049(6) 0.0102(6) 0.0052(6) B1 0.0173(7) 0.0170(6) 0.0212(6) -0.0019(5) 0.0034(5) -0.0010(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C2 1.3588(16) . ? F2 C3 1.3419(17) . ? F3 C4 1.3431(15) . ? F4 C5 1.3505(17) . ? F5 C6 1.3513(16) . ? F6 C8 1.3583(16) . ? F7 C9 1.3464(16) . ? F8 C10 1.3408(16) . ? F9 C11 1.3495(16) . ? F10 C12 1.3674(15) . ? F11 C17 1.3389(16) . ? F12 C17 1.3340(17) . ? F13 C17 1.3463(16) . ? F14 C18 1.3335(16) . ? F15 C18 1.3421(16) . ? F16 C18 1.3413(17) . ? O1 C13 1.3807(14) . ? O1 B1 1.4971(16) . ? N1 C24 1.5010(17) . ? N1 C19 1.5629(17) . ? N1 C23 1.5634(16) . ? C1 C6 1.3899(19) . ? C1 C2 1.3942(18) . ? C1 B1 1.6588(19) . ? C2 C3 1.3830(19) . ? C3 C4 1.376(2) . ? C4 C5 1.376(2) . ? C5 C6 1.3867(18) . ? C7 C8 1.3871(18) . ? C7 C12 1.3872(18) . ? C7 B1 1.6798(19) . ? C8 C9 1.385(2) . ? C9 C10 1.373(2) . ? C10 C11 1.378(2) . ? C11 C12 1.3781(18) . ? C13 C18 1.5422(18) . ? C13 C17 1.543(2) . ? C13 C14 1.5454(18) . ? C14 C15 1.519(2) . ? C15 C16 1.5288(19) . ? C16 B1 1.6139(19) . ? C19 C25 1.5279(18) . ? C19 C20 1.5282(18) . ? C19 C26 1.5289(18) . ? C20 C21 1.5204(19) . ? C21 C22 1.518(2) . ? C22 C23 1.5285(18) . ? C23 C27 1.5232(19) . ? C23 C28 1.5364(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O1 B1 125.11(10) . . ? C24 N1 C19 112.36(10) . . ? C24 N1 C23 112.00(10) . . ? C19 N1 C23 118.75(10) . . ? C6 C1 C2 113.46(12) . . ? C6 C1 B1 127.68(11) . . ? C2 C1 B1 118.86(11) . . ? F1 C2 C3 115.78(12) . . ? F1 C2 C1 119.46(12) . . ? C3 C2 C1 124.75(14) . . ? F2 C3 C4 120.39(13) . . ? F2 C3 C2 120.70(14) . . ? C4 C3 C2 118.90(13) . . ? F3 C4 C5 120.16(14) . . ? F3 C4 C3 120.54(14) . . ? C5 C4 C3 119.30(13) . . ? F4 C5 C4 119.38(12) . . ? F4 C5 C6 120.79(13) . . ? C4 C5 C6 119.83(13) . . ? F5 C6 C5 114.79(12) . . ? F5 C6 C1 121.46(11) . . ? C5 C6 C1 123.75(13) . . ? C8 C7 C12 112.81(12) . . ? C8 C7 B1 127.72(11) . . ? C12 C7 B1 119.43(11) . . ? F6 C8 C9 114.62(12) . . ? F6 C8 C7 120.76(12) . . ? C9 C8 C7 124.61(13) . . ? F7 C9 C10 119.97(13) . . ? F7 C9 C8 120.47(14) . . ? C10 C9 C8 119.56(13) . . ? F8 C10 C9 120.96(14) . . ? F8 C10 C11 120.37(15) . . ? C9 C10 C11 118.64(13) . . ? F9 C11 C12 120.96(13) . . ? F9 C11 C10 119.54(13) . . ? C12 C11 C10 119.50(13) . . ? F10 C12 C11 115.26(12) . . ? F10 C12 C7 119.83(11) . . ? C11 C12 C7 124.88(12) . . ? O1 C13 C18 108.09(10) . . ? O1 C13 C17 104.74(10) . . ? C18 C13 C17 109.06(11) . . ? O1 C13 C14 117.35(11) . . ? C18 C13 C14 109.17(11) . . ? C17 C13 C14 108.14(11) . . ? C15 C14 C13 113.37(11) . . ? C14 C15 C16 109.23(12) . . ? C15 C16 B1 110.13(11) . . ? F12 C17 F11 106.91(12) . . ? F12 C17 F13 106.80(11) . . ? F11 C17 F13 106.25(12) . . ? F12 C17 C13 113.53(11) . . ? F11 C17 C13 110.27(11) . . ? F13 C17 C13 112.65(12) . . ? F14 C18 F16 106.17(11) . . ? F14 C18 F15 106.66(11) . . ? F16 C18 F15 106.32(11) . . ? F14 C18 C13 112.83(11) . . ? F16 C18 C13 111.19(11) . . ? F15 C18 C13 113.18(11) . . ? C25 C19 C20 111.16(11) . . ? C25 C19 C26 109.85(11) . . ? C20 C19 C26 109.16(11) . . ? C25 C19 N1 112.33(11) . . ? C20 C19 N1 107.52(10) . . ? C26 C19 N1 106.67(10) . . ? C21 C20 C19 113.26(11) . . ? C22 C21 C20 108.79(12) . . ? C21 C22 C23 115.03(11) . . ? C27 C23 C22 112.50(12) . . ? C27 C23 C28 110.10(11) . . ? C22 C23 C28 108.35(11) . . ? C27 C23 N1 111.27(10) . . ? C22 C23 N1 107.75(10) . . ? C28 C23 N1 106.65(11) . . ? O1 B1 C16 110.05(10) . . ? O1 B1 C1 107.89(10) . . ? C16 B1 C1 111.32(10) . . ? O1 B1 C7 107.63(10) . . ? C16 B1 C7 115.00(11) . . ? C1 B1 C7 104.59(10) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 33.66 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.362 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.055 #===end