# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Kreitner, Christoph' 'Stanlake, Louisa' 'Stephan, Douglas' _publ_contact_author_name 'Stephan, Douglas' _publ_contact_author_email dstephan@chem.utoronto.ca _publ_section_title ; Ring Openings of Lactone and Ring Contractions of Lactide by Frustrated Lewis Pairs ; # Attachment '- 3-CK001_0m.cif' data_ck001_0m _database_code_depnum_ccdc_archive 'CCDC 817779' #TrackingRef '- 3-CK001_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C41 H41 B F15 O2 P' _chemical_formula_weight 892.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 10.9269(7) _cell_length_b 12.7792(8) _cell_length_c 14.1384(8) _cell_angle_alpha 88.639(3) _cell_angle_beta 85.623(3) _cell_angle_gamma 89.851(3) _cell_volume 1967.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9787 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 36.10 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 916 _exptl_absorpt_coefficient_mu 0.178 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6994 _exptl_absorpt_correction_T_max 0.7471 _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 67205 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 36.23 _reflns_number_total 18788 _reflns_number_gt 14079 _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^)+(0.0556P)^2^+0.3096P] 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 18788 _refine_ls_number_parameters 541 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1157 _refine_ls_wR_factor_gt 0.1047 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 0.275370(18) -0.211142(16) 0.252961(14) 0.01449(4) Uani 1 1 d . . . B1 B 0.00870(8) 0.23561(7) 0.29295(6) 0.01717(15) Uani 1 1 d . . . O1 O -0.02910(6) 0.12310(5) 0.30598(4) 0.01915(11) Uani 1 1 d . . . O2 O -0.10638(6) 0.12708(6) 0.45798(4) 0.02514(14) Uani 1 1 d . . . F2 F 0.02650(5) 0.45545(4) 0.25312(4) 0.02641(12) Uani 1 1 d . . . F3 F -0.15223(6) 0.58822(5) 0.20762(5) 0.03245(14) Uani 1 1 d . . . F4 F -0.38890(6) 0.52055(6) 0.21156(5) 0.03931(16) Uani 1 1 d . . . F5 F -0.44122(6) 0.31582(6) 0.25495(5) 0.03907(16) Uani 1 1 d . . . F6 F -0.26701(6) 0.18315(5) 0.29814(5) 0.03124(13) Uani 1 1 d . . . F8 F -0.07035(6) 0.14154(5) 0.12325(4) 0.03355(14) Uani 1 1 d . . . F9 F 0.05269(9) 0.12674(8) -0.04474(5) 0.0553(2) Uani 1 1 d . . . F10 F 0.27642(9) 0.22002(8) -0.07993(5) 0.0632(3) Uani 1 1 d . . . F11 F 0.37558(7) 0.32543(7) 0.06067(6) 0.0508(2) Uani 1 1 d . . . F12 F 0.25701(6) 0.33959(5) 0.23042(5) 0.03442(14) Uani 1 1 d . . . F14 F -0.04811(5) 0.38212(5) 0.45734(4) 0.02711(12) Uani 1 1 d . . . F15 F 0.07685(6) 0.39456(5) 0.60895(4) 0.03177(13) Uani 1 1 d . . . F16 F 0.28869(6) 0.28371(6) 0.62351(4) 0.03334(14) Uani 1 1 d . . . F17 F 0.36829(6) 0.15470(6) 0.48036(5) 0.03530(15) Uani 1 1 d . . . F18 F 0.24079(6) 0.13703(5) 0.32808(4) 0.02957(13) Uani 1 1 d . . . C1 C -0.10962(8) 0.31294(7) 0.27907(5) 0.01775(14) Uani 1 1 d . . . C2 C -0.08924(8) 0.41812(7) 0.25534(6) 0.01979(15) Uani 1 1 d . . . C3 C -0.17932(9) 0.48840(7) 0.23283(6) 0.02343(17) Uani 1 1 d . . . C4 C -0.29934(9) 0.45399(9) 0.23367(7) 0.02648(18) Uani 1 1 d . . . C5 C -0.32517(8) 0.35060(9) 0.25565(7) 0.02586(18) Uani 1 1 d . . . C6 C -0.23158(8) 0.28279(7) 0.27771(6) 0.02154(16) Uani 1 1 d . . . C7 C 0.08854(8) 0.23690(7) 0.18855(6) 0.02057(16) Uani 1 1 d . . . C8 C 0.04205(10) 0.18566(8) 0.11334(6) 0.02561(18) Uani 1 1 d . . . C9 C 0.10353(12) 0.17853(10) 0.02397(7) 0.0353(2) Uani 1 1 d . . . C10 C 0.21603(12) 0.22601(10) 0.00623(7) 0.0394(3) Uani 1 1 d . . . C11 C 0.26533(10) 0.27949(9) 0.07693(8) 0.0345(2) Uani 1 1 d . . . C12 C 0.20159(9) 0.28462(8) 0.16583(7) 0.02605(19) Uani 1 1 d . . . C13 C 0.09154(7) 0.26181(7) 0.38187(6) 0.01818(14) Uani 1 1 d . . . C14 C 0.05601(7) 0.32571(7) 0.45713(6) 0.01880(14) Uani 1 1 d . . . C15 C 0.11969(8) 0.33355(7) 0.53773(6) 0.02108(16) Uani 1 1 d . . . C16 C 0.22617(8) 0.27720(8) 0.54562(6) 0.02278(16) Uani 1 1 d . . . C17 C 0.26647(8) 0.21252(8) 0.47269(7) 0.02345(17) Uani 1 1 d . . . C18 C 0.19888(8) 0.20586(7) 0.39452(6) 0.02105(16) Uani 1 1 d . . . C19 C -0.07990(7) 0.08036(7) 0.38502(6) 0.01750(14) Uani 1 1 d . . . C20 C -0.10429(7) -0.03532(7) 0.37671(6) 0.01935(15) Uani 1 1 d . . . H20A H -0.1922 -0.0485 0.3953 0.023 Uiso 1 1 calc R . . H20B H -0.0561 -0.0740 0.4227 0.023 Uiso 1 1 calc R . . C21 C -0.07366(7) -0.08021(7) 0.27837(6) 0.01903(15) Uani 1 1 d . . . H21A H -0.1135 -0.0360 0.2311 0.023 Uiso 1 1 calc R . . H21B H -0.1097 -0.1511 0.2773 0.023 Uiso 1 1 calc R . . C22 C 0.06345(7) -0.08758(7) 0.24783(6) 0.01743(14) Uani 1 1 d . . . H22A H 0.1018 -0.0182 0.2541 0.021 Uiso 1 1 calc R . . H22B H 0.0739 -0.1065 0.1802 0.021 Uiso 1 1 calc R . . C23 C 0.12929(7) -0.16909(7) 0.30744(6) 0.01830(14) Uani 1 1 d . . . H23A H 0.0754 -0.2310 0.3190 0.022 Uiso 1 1 calc R . . H23B H 0.1423 -0.1391 0.3698 0.022 Uiso 1 1 calc R . . C24 C 0.34013(7) -0.30630(7) 0.33332(5) 0.01675(14) Uani 1 1 d . . . H24A H 0.4259 -0.3212 0.3073 0.020 Uiso 1 1 calc R . . C25 C 0.34813(8) -0.25974(7) 0.43262(6) 0.02141(16) Uani 1 1 d . . . H25A H 0.3935 -0.1927 0.4267 0.026 Uiso 1 1 calc R . . H25B H 0.2645 -0.2456 0.4615 0.026 Uiso 1 1 calc R . . C26 C 0.41387(8) -0.33650(8) 0.49614(6) 0.02341(17) Uani 1 1 d . . . H26A H 0.4992 -0.3468 0.4692 0.028 Uiso 1 1 calc R . . H26B H 0.4171 -0.3068 0.5600 0.028 Uiso 1 1 calc R . . C27 C 0.34806(8) -0.44190(8) 0.50484(6) 0.02415(17) Uani 1 1 d . . . H27A H 0.2653 -0.4328 0.5373 0.029 Uiso 1 1 calc R . . H27B H 0.3945 -0.4911 0.5437 0.029 Uiso 1 1 calc R . . C28 C 0.33634(9) -0.48742(7) 0.40699(7) 0.02431(17) Uani 1 1 d . . . H28A H 0.2897 -0.5538 0.4141 0.029 Uiso 1 1 calc R . . H28B H 0.4192 -0.5033 0.3774 0.029 Uiso 1 1 calc R . . C29 C 0.27115(8) -0.41166(7) 0.34204(6) 0.02130(15) Uani 1 1 d . . . H29A H 0.1857 -0.4003 0.3684 0.026 Uiso 1 1 calc R . . H29B H 0.2684 -0.4420 0.2785 0.026 Uiso 1 1 calc R . . C30 C 0.37879(7) -0.09771(7) 0.23670(6) 0.01710(14) Uani 1 1 d . . . H30A H 0.3555 -0.0494 0.2897 0.021 Uiso 1 1 calc R . . C31 C 0.51496(8) -0.12564(8) 0.24403(7) 0.02413(17) Uani 1 1 d . . . H31A H 0.5250 -0.1628 0.3052 0.029 Uiso 1 1 calc R . . H31B H 0.5427 -0.1729 0.1922 0.029 Uiso 1 1 calc R . . C32 C 0.59361(9) -0.02630(9) 0.23735(8) 0.0323(2) Uani 1 1 d . . . H32A H 0.5695 0.0184 0.2919 0.039 Uiso 1 1 calc R . . H32B H 0.6809 -0.0458 0.2409 0.039 Uiso 1 1 calc R . . C33 C 0.57909(9) 0.03550(9) 0.14538(8) 0.0296(2) Uani 1 1 d . . . H33A H 0.6101 -0.0065 0.0907 0.035 Uiso 1 1 calc R . . H33B H 0.6281 0.1006 0.1447 0.035 Uiso 1 1 calc R . . C34 C 0.44449(9) 0.06273(8) 0.13639(7) 0.02664(18) Uani 1 1 d . . . H34A H 0.4359 0.0990 0.0746 0.032 Uiso 1 1 calc R . . H34B H 0.4164 0.1111 0.1872 0.032 Uiso 1 1 calc R . . C35 C 0.36344(8) -0.03516(7) 0.14352(6) 0.02246(16) Uani 1 1 d . . . H35A H 0.3857 -0.0802 0.0888 0.027 Uiso 1 1 calc R . . H35B H 0.2764 -0.0143 0.1409 0.027 Uiso 1 1 calc R . . C36 C 0.25108(8) -0.26796(7) 0.13826(6) 0.01799(14) Uani 1 1 d . . . H36A H 0.2436 -0.2080 0.0923 0.022 Uiso 1 1 calc R . . C37 C 0.12938(8) -0.32969(7) 0.14079(6) 0.02120(15) Uani 1 1 d . . . H37A H 0.1286 -0.3848 0.1912 0.025 Uiso 1 1 calc R . . H37B H 0.0597 -0.2818 0.1562 0.025 Uiso 1 1 calc R . . C38 C 0.11368(10) -0.37994(8) 0.04550(7) 0.02821(19) Uani 1 1 d . . . H38A H 0.0378 -0.4225 0.0501 0.034 Uiso 1 1 calc R . . H38B H 0.1055 -0.3246 -0.0038 0.034 Uiso 1 1 calc R . . C39 C 0.22344(11) -0.44911(9) 0.01722(7) 0.0310(2) Uani 1 1 d . . . H39A H 0.2110 -0.4826 -0.0437 0.037 Uiso 1 1 calc R . . H39B H 0.2311 -0.5050 0.0661 0.037 Uiso 1 1 calc R . . C40 C 0.34067(10) -0.38407(9) 0.00701(7) 0.0319(2) Uani 1 1 d . . . H40A H 0.3337 -0.3293 -0.0430 0.038 Uiso 1 1 calc R . . H40B H 0.4111 -0.4296 -0.0125 0.038 Uiso 1 1 calc R . . C41 C 0.36340(8) -0.33266(8) 0.10083(6) 0.02450(17) Uani 1 1 d . . . H41A H 0.4360 -0.2864 0.0913 0.029 Uiso 1 1 calc R . . H41B H 0.3810 -0.3875 0.1485 0.029 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 P1 0.01379(8) 0.01489(9) 0.01470(8) -0.00021(6) -0.00052(6) 0.00118(6) B1 0.0194(4) 0.0151(4) 0.0167(3) -0.0020(3) 0.0011(3) -0.0004(3) O1 0.0252(3) 0.0159(3) 0.0159(2) -0.0009(2) 0.0017(2) -0.0013(2) O2 0.0281(3) 0.0279(3) 0.0187(3) -0.0045(2) 0.0042(2) -0.0003(3) F2 0.0232(2) 0.0190(3) 0.0366(3) 0.0011(2) -0.0006(2) -0.0030(2) F3 0.0438(4) 0.0201(3) 0.0334(3) 0.0034(2) -0.0045(3) 0.0059(3) F4 0.0335(3) 0.0454(4) 0.0395(4) 0.0034(3) -0.0083(3) 0.0185(3) F5 0.0201(3) 0.0565(5) 0.0416(4) 0.0030(3) -0.0095(3) -0.0037(3) F6 0.0258(3) 0.0272(3) 0.0414(3) 0.0035(3) -0.0081(2) -0.0094(2) F8 0.0414(4) 0.0368(4) 0.0235(3) -0.0034(2) -0.0077(2) -0.0048(3) F9 0.0802(6) 0.0671(6) 0.0197(3) -0.0143(3) -0.0084(3) 0.0169(5) F10 0.0725(6) 0.0826(7) 0.0289(3) 0.0086(4) 0.0276(4) 0.0316(5) F11 0.0332(3) 0.0542(5) 0.0596(5) 0.0194(4) 0.0248(3) 0.0061(3) F12 0.0272(3) 0.0342(3) 0.0408(3) 0.0004(3) 0.0041(3) -0.0086(3) F14 0.0239(3) 0.0325(3) 0.0258(3) -0.0110(2) -0.0048(2) 0.0111(2) F15 0.0359(3) 0.0371(3) 0.0233(3) -0.0125(2) -0.0052(2) 0.0020(3) F16 0.0288(3) 0.0449(4) 0.0278(3) 0.0023(3) -0.0125(2) -0.0043(3) F17 0.0231(3) 0.0379(4) 0.0455(4) 0.0030(3) -0.0078(3) 0.0100(3) F18 0.0285(3) 0.0281(3) 0.0320(3) -0.0075(2) 0.0004(2) 0.0109(2) C1 0.0196(3) 0.0184(4) 0.0154(3) -0.0026(3) -0.0013(2) -0.0004(3) C2 0.0213(3) 0.0187(4) 0.0193(3) -0.0021(3) -0.0010(3) 0.0001(3) C3 0.0306(4) 0.0208(4) 0.0190(3) -0.0008(3) -0.0028(3) 0.0048(3) C4 0.0263(4) 0.0331(5) 0.0204(4) -0.0008(3) -0.0045(3) 0.0097(4) C5 0.0192(4) 0.0371(5) 0.0218(4) -0.0014(3) -0.0048(3) 0.0003(3) C6 0.0214(4) 0.0233(4) 0.0202(3) -0.0011(3) -0.0036(3) -0.0021(3) C7 0.0243(4) 0.0178(4) 0.0187(3) 0.0011(3) 0.0031(3) 0.0037(3) C8 0.0341(5) 0.0246(4) 0.0178(3) 0.0000(3) -0.0003(3) 0.0067(4) C9 0.0508(6) 0.0384(6) 0.0163(4) -0.0016(4) -0.0001(4) 0.0179(5) C10 0.0481(6) 0.0447(7) 0.0224(4) 0.0079(4) 0.0144(4) 0.0239(5) C11 0.0301(5) 0.0345(6) 0.0356(5) 0.0122(4) 0.0154(4) 0.0115(4) C12 0.0252(4) 0.0238(4) 0.0275(4) 0.0051(3) 0.0069(3) 0.0043(3) C13 0.0173(3) 0.0170(4) 0.0201(3) -0.0015(3) 0.0003(3) 0.0002(3) C14 0.0169(3) 0.0193(4) 0.0203(3) -0.0026(3) -0.0017(3) 0.0008(3) C15 0.0222(4) 0.0216(4) 0.0196(3) -0.0031(3) -0.0014(3) -0.0026(3) C16 0.0204(4) 0.0258(4) 0.0226(4) 0.0037(3) -0.0057(3) -0.0056(3) C17 0.0168(3) 0.0237(4) 0.0297(4) 0.0042(3) -0.0029(3) 0.0011(3) C18 0.0198(3) 0.0194(4) 0.0236(4) -0.0017(3) 0.0010(3) 0.0022(3) C19 0.0158(3) 0.0192(4) 0.0173(3) 0.0000(3) -0.0006(2) 0.0011(3) C20 0.0167(3) 0.0186(4) 0.0222(3) 0.0015(3) 0.0019(3) 0.0002(3) C21 0.0146(3) 0.0179(4) 0.0249(4) -0.0023(3) -0.0028(3) -0.0002(3) C22 0.0161(3) 0.0161(3) 0.0200(3) -0.0014(3) -0.0009(2) 0.0017(3) C23 0.0162(3) 0.0202(4) 0.0182(3) -0.0002(3) 0.0006(2) 0.0024(3) C24 0.0165(3) 0.0171(3) 0.0165(3) 0.0010(3) -0.0009(2) 0.0025(3) C25 0.0244(4) 0.0232(4) 0.0167(3) -0.0009(3) -0.0024(3) 0.0045(3) C26 0.0210(4) 0.0299(5) 0.0193(3) 0.0026(3) -0.0031(3) 0.0033(3) C27 0.0200(4) 0.0301(5) 0.0218(4) 0.0090(3) -0.0012(3) 0.0040(3) C28 0.0252(4) 0.0202(4) 0.0274(4) 0.0068(3) -0.0036(3) 0.0007(3) C29 0.0222(4) 0.0197(4) 0.0222(4) 0.0034(3) -0.0039(3) -0.0007(3) C30 0.0158(3) 0.0165(3) 0.0190(3) 0.0001(3) -0.0013(2) -0.0003(3) C31 0.0157(3) 0.0263(4) 0.0306(4) 0.0037(3) -0.0041(3) -0.0006(3) C32 0.0216(4) 0.0366(6) 0.0393(5) 0.0055(4) -0.0089(4) -0.0099(4) C33 0.0225(4) 0.0295(5) 0.0361(5) 0.0039(4) 0.0007(4) -0.0085(4) C34 0.0255(4) 0.0210(4) 0.0327(4) 0.0054(3) 0.0006(3) -0.0029(3) C35 0.0193(3) 0.0231(4) 0.0249(4) 0.0062(3) -0.0032(3) -0.0023(3) C36 0.0196(3) 0.0181(4) 0.0163(3) -0.0006(3) -0.0018(2) -0.0002(3) C37 0.0204(3) 0.0205(4) 0.0232(4) -0.0025(3) -0.0040(3) -0.0021(3) C38 0.0316(5) 0.0284(5) 0.0260(4) -0.0040(4) -0.0101(3) -0.0040(4) C39 0.0416(5) 0.0276(5) 0.0241(4) -0.0092(4) -0.0028(4) -0.0022(4) C40 0.0360(5) 0.0383(6) 0.0210(4) -0.0109(4) 0.0033(4) -0.0008(4) C41 0.0221(4) 0.0298(5) 0.0215(4) -0.0079(3) 0.0013(3) 0.0020(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 P1 C23 1.8049(8) . ? P1 C24 1.8229(8) . ? P1 C36 1.8304(9) . ? P1 C30 1.8396(8) . ? B1 O1 1.5003(11) . ? B1 C13 1.6453(13) . ? B1 C1 1.6460(13) . ? B1 C7 1.6560(11) . ? O1 C19 1.3164(9) . ? O2 C19 1.2194(10) . ? F2 C2 1.3507(10) . ? F3 C3 1.3439(11) . ? F4 C4 1.3450(12) . ? F5 C5 1.3456(11) . ? F6 C6 1.3501(11) . ? F8 C8 1.3489(12) . ? F9 C9 1.3436(15) . ? F10 C10 1.3441(11) . ? F11 C11 1.3430(13) . ? F12 C12 1.3458(13) . ? F14 C14 1.3451(10) . ? F15 C15 1.3432(10) . ? F16 C16 1.3438(11) . ? F17 C17 1.3438(11) . ? F18 C18 1.3554(10) . ? C1 C6 1.3899(12) . ? C1 C2 1.3919(12) . ? C2 C3 1.3807(13) . ? C3 C4 1.3834(14) . ? C4 C5 1.3750(15) . ? C5 C6 1.3875(14) . ? C7 C8 1.3909(14) . ? C7 C12 1.3911(13) . ? C8 C9 1.3898(13) . ? C9 C10 1.3754(19) . ? C10 C11 1.368(2) . ? C11 C12 1.3926(13) . ? C13 C14 1.3880(11) . ? C13 C18 1.3930(12) . ? C14 C15 1.3855(13) . ? C15 C16 1.3771(13) . ? C16 C17 1.3819(14) . ? C17 C18 1.3797(14) . ? C19 C20 1.5117(12) . ? C20 C21 1.5296(12) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.5305(11) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.5361(12) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C29 1.5425(12) . ? C24 C25 1.5464(12) . ? C24 H24A 1.0000 . ? C25 C26 1.5290(13) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.5264(14) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.5278(14) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.5304(13) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C31 1.5399(12) . ? C30 C35 1.5445(12) . ? C30 H30A 1.0000 . ? C31 C32 1.5319(14) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.5237(15) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.5246(14) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.5314(13) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C41 1.5448(12) . ? C36 C37 1.5456(12) . ? C36 H36A 1.0000 . ? C37 C38 1.5277(13) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 C39 1.5225(16) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 C40 1.5245(16) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 C41 1.5314(13) . ? C40 H40A 0.9900 . ? C40 H40B 0.9900 . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? 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 P1 C24 107.81(4) . . ? C23 P1 C36 108.81(4) . . ? C24 P1 C36 111.65(4) . . ? C23 P1 C30 109.13(4) . . ? C24 P1 C30 109.04(4) . . ? C36 P1 C30 110.33(4) . . ? O1 B1 C13 106.37(7) . . ? O1 B1 C1 111.88(7) . . ? C13 B1 C1 116.17(7) . . ? O1 B1 C7 102.79(6) . . ? C13 B1 C7 113.56(7) . . ? C1 B1 C7 105.35(7) . . ? C19 O1 B1 125.24(7) . . ? C6 C1 C2 113.67(8) . . ? C6 C1 B1 126.70(8) . . ? C2 C1 B1 119.21(7) . . ? F2 C2 C3 116.67(8) . . ? F2 C2 C1 118.61(8) . . ? C3 C2 C1 124.72(8) . . ? F3 C3 C2 121.44(9) . . ? F3 C3 C4 119.59(9) . . ? C2 C3 C4 118.95(9) . . ? F4 C4 C5 120.64(9) . . ? F4 C4 C3 120.27(10) . . ? C5 C4 C3 119.09(9) . . ? F5 C5 C4 119.60(9) . . ? F5 C5 C6 120.48(9) . . ? C4 C5 C6 119.92(9) . . ? F6 C6 C5 115.05(8) . . ? F6 C6 C1 121.30(8) . . ? C5 C6 C1 123.65(9) . . ? C8 C7 C12 113.98(8) . . ? C8 C7 B1 119.18(8) . . ? C12 C7 B1 126.84(8) . . ? F8 C8 C9 115.57(10) . . ? F8 C8 C7 120.53(8) . . ? C9 C8 C7 123.87(10) . . ? F9 C9 C10 120.37(9) . . ? F9 C9 C8 120.20(12) . . ? C10 C9 C8 119.43(11) . . ? F10 C10 C11 120.54(12) . . ? F10 C10 C9 120.09(12) . . ? C11 C10 C9 119.36(9) . . ? F11 C11 C10 119.89(9) . . ? F11 C11 C12 120.36(12) . . ? C10 C11 C12 119.74(10) . . ? F12 C12 C7 121.05(8) . . ? F12 C12 C11 115.37(9) . . ? C7 C12 C11 123.58(10) . . ? C14 C13 C18 113.48(8) . . ? C14 C13 B1 125.63(7) . . ? C18 C13 B1 120.16(7) . . ? F14 C14 C15 115.23(7) . . ? F14 C14 C13 120.80(8) . . ? C15 C14 C13 123.92(8) . . ? F15 C15 C16 119.83(8) . . ? F15 C15 C14 120.24(8) . . ? C16 C15 C14 119.91(8) . . ? F16 C16 C15 120.59(9) . . ? F16 C16 C17 120.60(9) . . ? C15 C16 C17 118.80(8) . . ? F17 C17 C18 121.12(9) . . ? F17 C17 C16 119.61(9) . . ? C18 C17 C16 119.23(8) . . ? F18 C18 C17 115.86(8) . . ? F18 C18 C13 119.47(8) . . ? C17 C18 C13 124.65(8) . . ? O2 C19 O1 125.00(8) . . ? O2 C19 C20 122.20(7) . . ? O1 C19 C20 112.80(7) . . ? C19 C20 C21 115.54(7) . . ? C19 C20 H20A 108.4 . . ? C21 C20 H20A 108.4 . . ? C19 C20 H20B 108.4 . . ? C21 C20 H20B 108.4 . . ? H20A C20 H20B 107.5 . . ? C20 C21 C22 115.08(7) . . ? C20 C21 H21A 108.5 . . ? C22 C21 H21A 108.5 . . ? C20 C21 H21B 108.5 . . ? C22 C21 H21B 108.5 . . ? H21A C21 H21B 107.5 . . ? C21 C22 C23 112.22(6) . . ? C21 C22 H22A 109.2 . . ? C23 C22 H22A 109.2 . . ? C21 C22 H22B 109.2 . . ? C23 C22 H22B 109.2 . . ? H22A C22 H22B 107.9 . . ? C22 C23 P1 113.88(5) . . ? C22 C23 H23A 108.8 . . ? P1 C23 H23A 108.8 . . ? C22 C23 H23B 108.8 . . ? P1 C23 H23B 108.8 . . ? H23A C23 H23B 107.7 . . ? C29 C24 C25 110.07(7) . . ? C29 C24 P1 114.03(6) . . ? C25 C24 P1 110.63(6) . . ? C29 C24 H24A 107.3 . . ? C25 C24 H24A 107.3 . . ? P1 C24 H24A 107.3 . . ? C26 C25 C24 109.87(7) . . ? C26 C25 H25A 109.7 . . ? C24 C25 H25A 109.7 . . ? C26 C25 H25B 109.7 . . ? C24 C25 H25B 109.7 . . ? H25A C25 H25B 108.2 . . ? C27 C26 C25 111.10(8) . . ? C27 C26 H26A 109.4 . . ? C25 C26 H26A 109.4 . . ? C27 C26 H26B 109.4 . . ? C25 C26 H26B 109.4 . . ? H26A C26 H26B 108.0 . . ? C26 C27 C28 110.70(7) . . ? C26 C27 H27A 109.5 . . ? C28 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? C28 C27 H27B 109.5 . . ? H27A C27 H27B 108.1 . . ? C27 C28 C29 111.69(8) . . ? C27 C28 H28A 109.3 . . ? C29 C28 H28A 109.3 . . ? C27 C28 H28B 109.3 . . ? C29 C28 H28B 109.3 . . ? H28A C28 H28B 107.9 . . ? C28 C29 C24 109.83(7) . . ? C28 C29 H29A 109.7 . . ? C24 C29 H29A 109.7 . . ? C28 C29 H29B 109.7 . . ? C24 C29 H29B 109.7 . . ? H29A C29 H29B 108.2 . . ? C31 C30 C35 109.80(7) . . ? C31 C30 P1 113.58(6) . . ? C35 C30 P1 113.07(6) . . ? C31 C30 H30A 106.6 . . ? C35 C30 H30A 106.6 . . ? P1 C30 H30A 106.6 . . ? C32 C31 C30 110.34(8) . . ? C32 C31 H31A 109.6 . . ? C30 C31 H31A 109.6 . . ? C32 C31 H31B 109.6 . . ? C30 C31 H31B 109.6 . . ? H31A C31 H31B 108.1 . . ? C33 C32 C31 111.75(9) . . ? C33 C32 H32A 109.3 . . ? C31 C32 H32A 109.3 . . ? C33 C32 H32B 109.3 . . ? C31 C32 H32B 109.3 . . ? H32A C32 H32B 107.9 . . ? C32 C33 C34 110.27(8) . . ? C32 C33 H33A 109.6 . . ? C34 C33 H33A 109.6 . . ? C32 C33 H33B 109.6 . . ? C34 C33 H33B 109.6 . . ? H33A C33 H33B 108.1 . . ? C33 C34 C35 111.62(8) . . ? C33 C34 H34A 109.3 . . ? C35 C34 H34A 109.3 . . ? C33 C34 H34B 109.3 . . ? C35 C34 H34B 109.3 . . ? H34A C34 H34B 108.0 . . ? C34 C35 C30 111.23(8) . . ? C34 C35 H35A 109.4 . . ? C30 C35 H35A 109.4 . . ? C34 C35 H35B 109.4 . . ? C30 C35 H35B 109.4 . . ? H35A C35 H35B 108.0 . . ? C41 C36 C37 112.98(7) . . ? C41 C36 P1 111.38(6) . . ? C37 C36 P1 112.10(5) . . ? C41 C36 H36A 106.6 . . ? C37 C36 H36A 106.6 . . ? P1 C36 H36A 106.6 . . ? C38 C37 C36 111.10(7) . . ? C38 C37 H37A 109.4 . . ? C36 C37 H37A 109.4 . . ? C38 C37 H37B 109.4 . . ? C36 C37 H37B 109.4 . . ? H37A C37 H37B 108.0 . . ? C39 C38 C37 110.52(8) . . ? C39 C38 H38A 109.5 . . ? C37 C38 H38A 109.5 . . ? C39 C38 H38B 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 108.1 . . ? C38 C39 C40 110.21(9) . . ? C38 C39 H39A 109.6 . . ? C40 C39 H39A 109.6 . . ? C38 C39 H39B 109.6 . . ? C40 C39 H39B 109.6 . . ? H39A C39 H39B 108.1 . . ? C39 C40 C41 110.73(8) . . ? C39 C40 H40A 109.5 . . ? C41 C40 H40A 109.5 . . ? C39 C40 H40B 109.5 . . ? C41 C40 H40B 109.5 . . ? H40A C40 H40B 108.1 . . ? C40 C41 C36 111.28(8) . . ? C40 C41 H41A 109.4 . . ? C36 C41 H41A 109.4 . . ? C40 C41 H41B 109.4 . . ? C36 C41 H41B 109.4 . . ? H41A C41 H41B 108.0 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 36.23 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.517 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.055 # Attachment '- 4-ck003_0ma.cif' data_ck003_0ma _database_code_depnum_ccdc_archive 'CCDC 817780' #TrackingRef '- 4-ck003_0ma.cif' _audit_creation_method SHELXL-97 _chemical_formula_sum 'C34 H25 B F15 N O3' _chemical_formula_weight 791.36 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)/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 21.3723(9) _cell_length_b 17.9944(7) _cell_length_c 17.2320(7) _cell_angle_alpha 90.00 _cell_angle_beta 96.933(2) _cell_angle_gamma 90.00 _cell_volume 6578.7(5) _cell_formula_units_Z 8 _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 0.33 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.598 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3200 _exptl_absorpt_coefficient_mu 0.158 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9496 _exptl_absorpt_correction_T_max 0.9766 _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 57490 _diffrn_reflns_av_R_equivalents 0.0492 _diffrn_reflns_av_sigmaI/netI 0.0557 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 0.96 _diffrn_reflns_theta_max 27.55 _reflns_number_total 15169 _reflns_number_gt 9813 _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^)+(0.0411P)^2^+2.2656P] 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 fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 15169 _refine_ls_number_parameters 977 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0834 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1058 _refine_ls_wR_factor_gt 0.0902 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 N1 N 0.94419(8) 0.27673(9) 0.55461(8) 0.0200(4) Uani 1 1 d . . . N2 N 0.52057(8) 0.44202(9) 0.21274(9) 0.0205(4) Uani 1 1 d . . . B1 B 0.89424(11) 0.59704(12) 0.17418(12) 0.0180(5) Uani 1 1 d . . . B2 B 0.39395(11) 0.81543(12) -0.09429(12) 0.0189(5) Uani 1 1 d . . . F1 F 1.15270(6) 0.67499(7) 0.13398(7) 0.0352(3) Uani 1 1 d . . . F2 F 0.72589(6) 0.52888(8) -0.10942(7) 0.0443(4) Uani 1 1 d . . . F3 F 0.77468(6) 0.52009(7) 0.16237(6) 0.0303(3) Uani 1 1 d . . . F4 F 0.69837(6) 0.48483(8) 0.03334(7) 0.0415(3) Uani 1 1 d . . . F5 F 0.97623(5) 0.52324(6) 0.07684(6) 0.0263(3) Uani 1 1 d . . . F6 F 0.97046(5) 0.72912(7) 0.24720(6) 0.0280(3) Uani 1 1 d . . . F7 F 1.08927(6) 0.75809(7) 0.23123(7) 0.0330(3) Uani 1 1 d . . . F8 F 1.09482(6) 0.55599(7) 0.05914(7) 0.0315(3) Uani 1 1 d . . . F9 F 0.86679(6) 0.74630(7) 0.12443(7) 0.0330(3) Uani 1 1 d . . . F10 F 0.78929(7) 0.84312(7) 0.18151(9) 0.0475(4) Uani 1 1 d . . . F11 F 0.73058(6) 0.80709(8) 0.30807(9) 0.0512(4) Uani 1 1 d . . . F12 F 0.82698(6) 0.57451(7) 0.32121(7) 0.0343(3) Uani 1 1 d . . . F13 F 0.75481(6) 0.67346(9) 0.37926(7) 0.0459(4) Uani 1 1 d . . . F14 F 0.91011(5) 0.64251(7) 0.00611(6) 0.0296(3) Uani 1 1 d . . . F15 F 0.83403(6) 0.60854(8) -0.11987(6) 0.0381(3) Uani 1 1 d . . . F32 F 0.36289(5) 0.86269(7) -0.25560(6) 0.0299(3) Uani 1 1 d . . . F33 F 0.28256(6) 0.80155(8) -0.36630(6) 0.0359(3) Uani 1 1 d . . . F34 F 0.21168(6) 0.68096(7) -0.33268(7) 0.0363(3) Uani 1 1 d . . . F35 F 0.22417(6) 0.62689(7) -0.18550(7) 0.0355(3) Uani 1 1 d . . . F36 F 0.30599(6) 0.68431(6) -0.07420(6) 0.0285(3) Uani 1 1 d . . . F38 F 0.30386(6) 0.82571(7) 0.02219(7) 0.0309(3) Uani 1 1 d . . . F39 F 0.23776(6) 0.94262(7) 0.05601(7) 0.0384(3) Uani 1 1 d . . . F40 F 0.25233(6) 1.07604(7) -0.01434(8) 0.0387(3) Uani 1 1 d . . . F41 F 0.33835(6) 1.08919(7) -0.11734(8) 0.0390(3) Uani 1 1 d . . . F42 F 0.40536(6) 0.97378(7) -0.15348(7) 0.0312(3) Uani 1 1 d . . . F44 F 0.44912(5) 0.74314(6) -0.23210(6) 0.0273(3) Uani 1 1 d . . . F45 F 0.56084(6) 0.77059(8) -0.27515(7) 0.0370(3) Uani 1 1 d . . . F46 F 0.63832(6) 0.87389(9) -0.19958(8) 0.0464(4) Uani 1 1 d . . . F47 F 0.60211(6) 0.94496(8) -0.07247(8) 0.0448(4) Uani 1 1 d . . . F48 F 0.49127(6) 0.91582(7) -0.02438(7) 0.0329(3) Uani 1 1 d . . . O1 O 0.90232(6) 0.52256(7) 0.21498(7) 0.0197(3) Uani 1 1 d . . . O1S O 0.61747(10) 0.65498(13) 0.07394(12) 0.0731(7) Uani 1 1 d . . . O2S O 0.84249(8) 0.44479(11) 0.61983(10) 0.0503(5) Uani 1 1 d . . . O2 O 0.96335(7) 0.56705(7) 0.32008(7) 0.0239(3) Uani 1 1 d . . . O3 O 0.40855(6) 0.77120(7) -0.01976(7) 0.0203(3) Uani 1 1 d . . . O4 O 0.44329(7) 0.67040(8) -0.07836(7) 0.0257(3) Uani 1 1 d . . . C1 C 0.85242(9) 0.65565(11) 0.21987(11) 0.0209(4) Uani 1 1 d . . . C1S C 0.6086(2) 0.6772(4) -0.0014(2) 0.194(4) Uani 1 1 d . . . H1SA H 0.5657 0.6984 -0.0127 0.233 Uiso 1 1 calc R . . H1SB H 0.6110 0.6333 -0.0355 0.233 Uiso 1 1 calc R . . C2 C 0.82109(10) 0.64074(12) 0.28431(11) 0.0250(5) Uani 1 1 d . . . C2S C 0.65272(14) 0.7305(2) -0.02031(18) 0.0750(10) Uani 1 1 d . . . H2SA H 0.6338 0.7807 -0.0245 0.090 Uiso 1 1 calc R . . H2SB H 0.6689 0.7180 -0.0702 0.090 Uiso 1 1 calc R . . C3 C 0.78197(10) 0.69090(14) 0.31531(12) 0.0309(5) Uani 1 1 d . . . C3S C 0.70438(12) 0.72615(15) 0.04715(14) 0.0439(6) Uani 1 1 d . . . H3SA H 0.7396 0.6945 0.0342 0.053 Uiso 1 1 calc R . . H3SB H 0.7208 0.7762 0.0625 0.053 Uiso 1 1 calc R . . C4 C 0.77072(10) 0.75873(14) 0.28080(14) 0.0339(6) Uani 1 1 d . . . C4S C 0.67150(13) 0.69177(18) 0.11037(16) 0.0543(8) Uani 1 1 d . . . H4SA H 0.6998 0.6560 0.1409 0.065 Uiso 1 1 calc R . . H4SB H 0.6592 0.7306 0.1463 0.065 Uiso 1 1 calc R . . C5S C 0.87998(12) 0.50867(15) 0.63983(14) 0.0430(6) Uani 1 1 d . . . H5SA H 0.8603 0.5532 0.6134 0.052 Uiso 1 1 calc R . . H5SB H 0.9226 0.5022 0.6237 0.052 Uiso 1 1 calc R . . C5 C 0.80015(10) 0.77695(12) 0.21684(14) 0.0320(5) Uani 1 1 d . . . C6S C 0.88418(12) 0.51734(15) 0.72784(13) 0.0422(6) Uani 1 1 d . . . H6SA H 0.9206 0.4898 0.7548 0.051 Uiso 1 1 calc R . . H6SB H 0.8873 0.5703 0.7435 0.051 Uiso 1 1 calc R . . C6 C 0.83954(10) 0.72574(12) 0.18835(12) 0.0250(5) Uani 1 1 d . . . C7S C 0.82228(12) 0.48356(14) 0.74470(13) 0.0391(6) Uani 1 1 d . . . H7SA H 0.8251 0.4648 0.7990 0.047 Uiso 1 1 calc R . . H7SB H 0.7874 0.5200 0.7359 0.047 Uiso 1 1 calc R . . C7 C 0.96548(9) 0.62507(11) 0.16119(10) 0.0184(4) Uani 1 1 d . . . C8S C 0.81337(12) 0.42070(14) 0.68641(13) 0.0397(6) Uani 1 1 d . . . H8SA H 0.8337 0.3748 0.7088 0.048 Uiso 1 1 calc R . . H8SB H 0.7680 0.4107 0.6714 0.048 Uiso 1 1 calc R . . C8 C 0.99821(9) 0.68415(11) 0.19862(10) 0.0210(4) Uani 1 1 d . . . C9 C 1.06006(10) 0.70106(11) 0.19107(11) 0.0221(4) Uani 1 1 d . . . C10 C 1.09250(9) 0.65911(12) 0.14264(12) 0.0242(5) Uani 1 1 d . . . C11 C 1.06302(9) 0.59949(11) 0.10438(11) 0.0217(4) Uani 1 1 d . . . C12 C 1.00150(9) 0.58391(11) 0.11507(11) 0.0201(4) Uani 1 1 d . . . C13 C 0.84905(9) 0.57896(11) 0.09152(11) 0.0190(4) Uani 1 1 d . . . C14 C 0.79286(10) 0.54010(11) 0.09297(11) 0.0221(4) Uani 1 1 d . . . C15 C 0.75191(10) 0.52253(12) 0.02732(12) 0.0271(5) Uani 1 1 d . . . C16 C 0.76565(10) 0.54497(13) -0.04489(12) 0.0289(5) Uani 1 1 d . . . C17 C 0.81931(10) 0.58540(12) -0.04979(11) 0.0250(5) Uani 1 1 d . . . C18 C 0.85891(9) 0.60132(11) 0.01737(11) 0.0212(4) Uani 1 1 d . . . C19 C 0.93516(9) 0.51634(11) 0.28472(10) 0.0191(4) Uani 1 1 d . . . C20 C 0.93517(11) 0.43799(11) 0.31596(11) 0.0251(5) Uani 1 1 d . . . H20A H 0.9713 0.4106 0.2990 0.030 Uiso 1 1 calc R . . H20B H 0.8961 0.4126 0.2933 0.030 Uiso 1 1 calc R . . C21 C 0.93938(10) 0.43512(11) 0.40496(11) 0.0243(5) Uani 1 1 d . . . H21A H 0.9015 0.4588 0.4218 0.029 Uiso 1 1 calc R . . H21B H 0.9767 0.4637 0.4279 0.029 Uiso 1 1 calc R . . C22 C 0.94442(10) 0.35546(11) 0.43553(11) 0.0236(4) Uani 1 1 d . . . H22A H 0.9087 0.3258 0.4100 0.028 Uiso 1 1 calc R . . H22B H 0.9840 0.3328 0.4224 0.028 Uiso 1 1 calc R . . C23 C 0.94361(10) 0.35404(11) 0.52376(11) 0.0211(4) Uani 1 1 d . . . H23A H 0.9809 0.3811 0.5493 0.025 Uiso 1 1 calc R . . H23B H 0.9054 0.3799 0.5369 0.025 Uiso 1 1 calc R . . C24 C 0.88795(11) 0.24068(12) 0.55554(11) 0.0276(5) Uani 1 1 d . . . C25 C 0.88789(13) 0.16960(14) 0.58441(13) 0.0393(6) Uani 1 1 d . . . H25A H 0.8491 0.1439 0.5849 0.047 Uiso 1 1 calc R . . C26 C 0.94309(15) 0.13549(14) 0.61246(13) 0.0442(7) Uani 1 1 d . . . H26A H 0.9427 0.0868 0.6337 0.053 Uiso 1 1 calc R . . C27 C 0.99910(13) 0.17199(13) 0.60980(12) 0.0363(6) Uani 1 1 d . . . H27A H 1.0376 0.1480 0.6286 0.044 Uiso 1 1 calc R . . C28 C 1.00028(10) 0.24373(12) 0.57995(10) 0.0249(5) Uani 1 1 d . . . C29 C 1.06023(10) 0.28461(14) 0.57699(13) 0.0362(6) Uani 1 1 d . . . H29A H 1.0634 0.3002 0.5231 0.054 Uiso 1 1 calc R . . H29B H 1.0958 0.2521 0.5951 0.054 Uiso 1 1 calc R . . H29C H 1.0611 0.3285 0.6108 0.054 Uiso 1 1 calc R . . C30 C 0.82747(11) 0.27824(14) 0.52660(14) 0.0384(6) Uani 1 1 d . . . H30A H 0.8298 0.2976 0.4739 0.058 Uiso 1 1 calc R . . H30B H 0.8201 0.3194 0.5617 0.058 Uiso 1 1 calc R . . H30C H 0.7928 0.2425 0.5252 0.058 Uiso 1 1 calc R . . C31 C 0.34141(9) 0.77553(11) -0.15937(11) 0.0191(4) Uani 1 1 d . . . C32 C 0.32994(9) 0.80302(11) -0.23504(11) 0.0212(4) Uani 1 1 d . . . C33 C 0.28819(10) 0.77279(12) -0.29392(11) 0.0248(5) Uani 1 1 d . . . C34 C 0.25280(9) 0.71283(12) -0.27739(12) 0.0251(5) Uani 1 1 d . . . C35 C 0.25967(10) 0.68511(11) -0.20252(12) 0.0249(5) Uani 1 1 d . . . C36 C 0.30289(9) 0.71624(11) -0.14574(11) 0.0212(4) Uani 1 1 d . . . C37 C 0.35851(9) 0.89155(11) -0.06874(10) 0.0194(4) Uani 1 1 d . . . C38 C 0.31455(9) 0.88982(11) -0.01537(11) 0.0218(4) Uani 1 1 d . . . C39 C 0.27905(10) 0.94975(12) 0.00334(11) 0.0245(5) Uani 1 1 d . . . C40 C 0.28593(10) 1.01684(12) -0.03190(12) 0.0256(5) Uani 1 1 d . . . C41 C 0.32889(10) 1.02271(11) -0.08436(12) 0.0255(5) Uani 1 1 d . . . C42 C 0.36370(9) 0.96158(11) -0.10144(11) 0.0221(4) Uani 1 1 d . . . C43 C 0.46197(9) 0.83042(11) -0.12716(10) 0.0195(4) Uani 1 1 d . . . C44 C 0.48449(9) 0.79449(11) -0.18941(11) 0.0217(4) Uani 1 1 d . . . C45 C 0.54264(10) 0.80751(12) -0.21358(12) 0.0264(5) Uani 1 1 d . . . C46 C 0.58213(10) 0.85912(13) -0.17532(12) 0.0299(5) Uani 1 1 d . . . C47 C 0.56329(10) 0.89526(12) -0.11193(12) 0.0289(5) Uani 1 1 d . . . C48 C 0.50543(10) 0.87966(12) -0.08885(11) 0.0234(5) Uani 1 1 d . . . C49 C 0.43187(9) 0.70331(11) -0.01993(11) 0.0207(4) Uani 1 1 d . . . C50 C 0.44385(11) 0.67084(11) 0.06136(11) 0.0263(5) Uani 1 1 d . . . H50A H 0.4057 0.6774 0.0880 0.032 Uiso 1 1 calc R . . H50B H 0.4787 0.6985 0.0916 0.032 Uiso 1 1 calc R . . C51 C 0.46068(10) 0.58870(11) 0.06112(11) 0.0238(5) Uani 1 1 d . . . H51A H 0.4946 0.5813 0.0275 0.029 Uiso 1 1 calc R . . H51B H 0.4234 0.5603 0.0379 0.029 Uiso 1 1 calc R . . C52 C 0.48244(11) 0.55755(12) 0.14236(11) 0.0264(5) Uani 1 1 d . . . H52A H 0.5197 0.5855 0.1665 0.032 Uiso 1 1 calc R . . H52B H 0.4484 0.5629 0.1762 0.032 Uiso 1 1 calc R . . C53 C 0.49925(11) 0.47586(12) 0.13516(11) 0.0254(5) Uani 1 1 d . . . H53A H 0.4619 0.4485 0.1102 0.030 Uiso 1 1 calc R . . H53B H 0.5332 0.4710 0.1011 0.030 Uiso 1 1 calc R . . C54 C 0.47706(10) 0.41221(11) 0.25491(11) 0.0234(5) Uani 1 1 d . . . C55 C 0.49638(10) 0.38509(12) 0.32893(11) 0.0264(5) Uani 1 1 d . . . H55A H 0.4662 0.3659 0.3598 0.032 Uiso 1 1 calc R . . C56 C 0.55925(11) 0.38582(12) 0.35818(12) 0.0290(5) Uani 1 1 d . . . H56A H 0.5727 0.3666 0.4088 0.035 Uiso 1 1 calc R . . C57 C 0.60227(11) 0.41466(12) 0.31341(12) 0.0293(5) Uani 1 1 d . . . H57A H 0.6457 0.4150 0.3332 0.035 Uiso 1 1 calc R . . C58 C 0.58335(10) 0.44320(12) 0.24012(11) 0.0248(5) Uani 1 1 d . . . C59 C 0.40947(10) 0.40673(14) 0.22037(12) 0.0329(5) Uani 1 1 d . . . H59A H 0.3940 0.4561 0.2035 0.049 Uiso 1 1 calc R . . H59B H 0.3842 0.3874 0.2597 0.049 Uiso 1 1 calc R . . H59C H 0.4060 0.3731 0.1753 0.049 Uiso 1 1 calc R . . C60 C 0.62983(11) 0.47333(14) 0.18995(13) 0.0356(5) Uani 1 1 d . . . H60A H 0.6168 0.5233 0.1719 0.053 Uiso 1 1 calc R . . H60B H 0.6315 0.4407 0.1447 0.053 Uiso 1 1 calc R . . H60C H 0.6716 0.4758 0.2203 0.053 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 0.0294(10) 0.0172(9) 0.0135(7) 0.0002(7) 0.0031(7) 0.0012(7) N2 0.0291(10) 0.0174(9) 0.0150(8) 0.0012(7) 0.0027(7) 0.0045(7) B1 0.0224(12) 0.0160(12) 0.0158(10) 0.0020(9) 0.0027(9) -0.0012(9) B2 0.0224(12) 0.0166(12) 0.0172(10) 0.0025(9) 0.0007(9) -0.0002(9) F1 0.0222(7) 0.0400(8) 0.0441(7) 0.0000(6) 0.0075(6) -0.0085(6) F2 0.0374(8) 0.0652(10) 0.0270(7) -0.0072(7) -0.0104(6) -0.0077(7) F3 0.0311(7) 0.0353(7) 0.0250(6) 0.0067(5) 0.0060(5) -0.0095(6) F4 0.0295(7) 0.0517(9) 0.0419(7) -0.0004(7) -0.0011(6) -0.0187(6) F5 0.0284(7) 0.0211(6) 0.0295(6) -0.0074(5) 0.0042(5) -0.0051(5) F6 0.0330(7) 0.0269(7) 0.0251(6) -0.0100(5) 0.0069(5) -0.0040(5) F7 0.0348(7) 0.0284(7) 0.0351(7) -0.0077(6) 0.0014(5) -0.0147(6) F8 0.0294(7) 0.0316(7) 0.0353(7) -0.0062(6) 0.0111(5) 0.0029(6) F9 0.0411(8) 0.0242(7) 0.0345(7) 0.0103(6) 0.0075(6) 0.0021(6) F10 0.0466(9) 0.0219(7) 0.0721(10) 0.0011(7) -0.0002(7) 0.0102(6) F11 0.0330(8) 0.0498(10) 0.0716(10) -0.0263(8) 0.0094(7) 0.0116(7) F12 0.0366(8) 0.0394(8) 0.0290(6) 0.0117(6) 0.0120(6) 0.0043(6) F13 0.0344(8) 0.0712(11) 0.0351(7) -0.0070(7) 0.0165(6) 0.0023(7) F14 0.0287(7) 0.0374(8) 0.0225(6) 0.0095(5) 0.0025(5) -0.0093(6) F15 0.0396(8) 0.0582(9) 0.0160(6) 0.0055(6) 0.0012(5) -0.0014(7) F32 0.0301(7) 0.0328(7) 0.0259(6) 0.0095(5) -0.0007(5) -0.0078(6) F33 0.0329(7) 0.0540(9) 0.0189(6) 0.0051(6) -0.0040(5) -0.0009(6) F34 0.0311(7) 0.0406(8) 0.0345(7) -0.0147(6) -0.0076(6) -0.0038(6) F35 0.0348(7) 0.0255(7) 0.0462(8) -0.0042(6) 0.0046(6) -0.0116(6) F36 0.0339(7) 0.0262(7) 0.0252(6) 0.0053(5) 0.0030(5) -0.0068(5) F38 0.0326(7) 0.0255(7) 0.0366(7) 0.0077(6) 0.0121(5) 0.0015(5) F39 0.0398(8) 0.0391(8) 0.0397(7) -0.0008(6) 0.0181(6) 0.0073(6) F40 0.0424(8) 0.0287(8) 0.0459(8) -0.0065(6) 0.0092(6) 0.0128(6) F41 0.0504(9) 0.0180(7) 0.0506(8) 0.0097(6) 0.0137(7) 0.0065(6) F42 0.0374(7) 0.0233(7) 0.0352(7) 0.0078(5) 0.0142(6) 0.0032(6) F44 0.0275(7) 0.0278(7) 0.0269(6) -0.0086(5) 0.0052(5) -0.0022(5) F45 0.0343(7) 0.0455(8) 0.0341(7) -0.0004(6) 0.0158(6) 0.0042(6) F46 0.0230(7) 0.0656(10) 0.0517(8) 0.0143(7) 0.0087(6) -0.0089(7) F47 0.0352(8) 0.0515(9) 0.0444(8) -0.0003(7) -0.0089(6) -0.0210(7) F48 0.0355(7) 0.0353(8) 0.0266(6) -0.0103(6) -0.0012(5) -0.0074(6) O1 0.0252(8) 0.0173(7) 0.0160(6) 0.0023(5) 0.0001(5) -0.0012(6) O1S 0.0715(15) 0.0938(17) 0.0551(12) -0.0015(12) 0.0124(11) -0.0422(13) O2S 0.0398(10) 0.0696(14) 0.0427(10) -0.0234(9) 0.0102(8) -0.0080(9) O2 0.0309(8) 0.0187(8) 0.0211(7) 0.0001(6) -0.0006(6) -0.0026(6) O3 0.0261(8) 0.0175(7) 0.0169(6) 0.0014(6) 0.0011(5) 0.0040(6) O4 0.0355(9) 0.0236(8) 0.0178(7) -0.0005(6) 0.0031(6) 0.0069(6) C1 0.0191(10) 0.0225(11) 0.0206(9) -0.0017(8) 0.0002(8) -0.0015(8) C1S 0.103(3) 0.416(10) 0.054(2) 0.072(4) -0.034(2) -0.170(5) C2 0.0224(11) 0.0291(12) 0.0229(10) 0.0004(9) 0.0004(8) -0.0013(9) C2S 0.0506(19) 0.116(3) 0.0557(18) 0.0338(19) -0.0047(15) -0.0096(19) C3 0.0217(11) 0.0445(15) 0.0271(11) -0.0093(10) 0.0051(9) -0.0016(10) C3S 0.0386(15) 0.0417(16) 0.0504(15) 0.0021(12) 0.0017(12) -0.0028(12) C4 0.0208(11) 0.0366(14) 0.0438(13) -0.0173(11) 0.0027(10) 0.0040(10) C4S 0.0391(16) 0.078(2) 0.0460(15) 0.0004(15) 0.0047(13) -0.0078(15) C5S 0.0365(14) 0.0506(17) 0.0425(14) -0.0097(12) 0.0070(11) 0.0003(12) C5 0.0287(12) 0.0201(12) 0.0448(13) -0.0032(10) -0.0059(10) 0.0037(9) C6S 0.0425(15) 0.0463(16) 0.0353(13) -0.0062(12) -0.0061(11) 0.0038(12) C6 0.0243(11) 0.0233(12) 0.0267(10) 0.0001(9) 0.0006(9) -0.0025(9) C7S 0.0415(15) 0.0445(16) 0.0309(12) -0.0006(11) 0.0029(11) 0.0079(12) C7 0.0225(10) 0.0173(10) 0.0149(9) 0.0038(8) -0.0005(8) -0.0013(8) C8S 0.0412(15) 0.0416(15) 0.0342(12) -0.0004(11) -0.0034(11) 0.0065(12) C8 0.0275(11) 0.0210(11) 0.0146(9) 0.0011(8) 0.0034(8) 0.0016(9) C9 0.0266(11) 0.0182(11) 0.0206(10) 0.0018(8) -0.0008(8) -0.0076(9) C10 0.0184(11) 0.0273(12) 0.0269(10) 0.0065(9) 0.0030(8) -0.0036(9) C11 0.0233(11) 0.0213(11) 0.0213(10) 0.0007(8) 0.0055(8) 0.0039(9) C12 0.0255(11) 0.0160(10) 0.0178(9) 0.0005(8) -0.0009(8) -0.0012(8) C13 0.0216(10) 0.0155(10) 0.0196(9) 0.0006(8) 0.0009(8) 0.0007(8) C14 0.0265(11) 0.0189(11) 0.0214(10) 0.0019(8) 0.0047(8) -0.0005(9) C15 0.0199(11) 0.0279(12) 0.0329(11) -0.0001(10) 0.0012(9) -0.0046(9) C16 0.0274(12) 0.0344(13) 0.0228(10) -0.0063(9) -0.0058(9) 0.0019(10) C17 0.0275(12) 0.0306(12) 0.0168(9) 0.0025(9) 0.0023(8) 0.0043(9) C18 0.0211(11) 0.0208(11) 0.0219(10) 0.0012(8) 0.0036(8) 0.0003(8) C19 0.0220(11) 0.0195(11) 0.0163(9) 0.0020(8) 0.0042(8) 0.0015(8) C20 0.0365(13) 0.0175(11) 0.0202(10) 0.0036(8) -0.0015(9) -0.0006(9) C21 0.0329(12) 0.0199(11) 0.0202(10) 0.0035(8) 0.0038(9) 0.0013(9) C22 0.0316(12) 0.0210(11) 0.0178(9) 0.0022(8) 0.0019(8) 0.0000(9) C23 0.0287(11) 0.0163(10) 0.0185(9) 0.0018(8) 0.0036(8) 0.0014(8) C24 0.0368(13) 0.0269(12) 0.0207(10) -0.0049(9) 0.0101(9) -0.0049(10) C25 0.0583(17) 0.0295(14) 0.0349(13) -0.0048(11) 0.0252(12) -0.0090(12) C26 0.089(2) 0.0215(13) 0.0266(12) 0.0028(10) 0.0273(13) 0.0042(14) C27 0.0622(17) 0.0297(13) 0.0176(10) 0.0008(9) 0.0081(11) 0.0218(12) C28 0.0362(12) 0.0270(12) 0.0115(9) -0.0047(8) 0.0022(8) 0.0099(10) C29 0.0306(13) 0.0405(15) 0.0353(12) -0.0128(11) -0.0048(10) 0.0099(11) C30 0.0308(13) 0.0428(15) 0.0423(13) -0.0073(12) 0.0080(11) -0.0061(11) C31 0.0194(10) 0.0170(10) 0.0210(9) -0.0030(8) 0.0030(8) 0.0019(8) C32 0.0181(10) 0.0222(11) 0.0238(10) 0.0018(8) 0.0047(8) -0.0014(8) C33 0.0239(11) 0.0327(13) 0.0175(9) 0.0004(9) 0.0013(8) 0.0048(9) C34 0.0182(10) 0.0278(12) 0.0280(11) -0.0118(9) -0.0029(8) 0.0015(9) C35 0.0220(11) 0.0192(11) 0.0337(11) -0.0041(9) 0.0048(9) -0.0021(9) C36 0.0233(11) 0.0205(11) 0.0202(9) 0.0001(8) 0.0045(8) 0.0030(8) C37 0.0202(10) 0.0196(11) 0.0172(9) -0.0018(8) -0.0028(8) -0.0007(8) C38 0.0241(11) 0.0185(11) 0.0218(10) 0.0020(8) -0.0015(8) -0.0016(8) C39 0.0246(11) 0.0285(12) 0.0212(10) -0.0035(9) 0.0060(9) 0.0002(9) C40 0.0264(12) 0.0228(12) 0.0264(10) -0.0075(9) -0.0014(9) 0.0066(9) C41 0.0325(12) 0.0154(11) 0.0273(11) 0.0031(9) -0.0012(9) 0.0012(9) C42 0.0232(11) 0.0233(12) 0.0200(9) 0.0000(8) 0.0033(8) -0.0004(9) C43 0.0226(11) 0.0181(10) 0.0171(9) 0.0047(8) -0.0008(8) 0.0020(8) C44 0.0226(11) 0.0202(11) 0.0216(10) 0.0050(8) -0.0002(8) 0.0002(8) C45 0.0258(12) 0.0309(13) 0.0230(10) 0.0051(9) 0.0055(9) 0.0052(9) C46 0.0179(11) 0.0390(14) 0.0323(12) 0.0154(10) 0.0016(9) -0.0011(10) C47 0.0241(12) 0.0321(13) 0.0276(11) 0.0060(10) -0.0089(9) -0.0091(9) C48 0.0262(12) 0.0234(11) 0.0194(10) 0.0032(8) -0.0021(8) -0.0006(9) C49 0.0231(11) 0.0185(11) 0.0201(10) 0.0010(8) 0.0006(8) 0.0000(8) C50 0.0373(13) 0.0226(12) 0.0186(10) 0.0014(9) 0.0024(9) 0.0079(9) C51 0.0333(12) 0.0199(11) 0.0172(9) 0.0028(8) -0.0004(8) 0.0032(9) C52 0.0396(13) 0.0238(12) 0.0159(9) 0.0010(8) 0.0038(9) 0.0089(10) C53 0.0374(13) 0.0249(12) 0.0136(9) 0.0028(8) 0.0026(9) 0.0090(10) C54 0.0292(12) 0.0207(11) 0.0205(10) -0.0018(8) 0.0033(9) 0.0032(9) C55 0.0356(13) 0.0245(12) 0.0201(10) 0.0020(9) 0.0076(9) 0.0000(9) C56 0.0390(14) 0.0296(13) 0.0178(10) 0.0028(9) 0.0003(9) 0.0062(10) C57 0.0299(12) 0.0316(13) 0.0251(10) -0.0023(10) -0.0016(9) 0.0063(10) C58 0.0295(12) 0.0211(11) 0.0243(10) -0.0010(9) 0.0054(9) 0.0027(9) C59 0.0301(13) 0.0401(14) 0.0276(11) -0.0013(10) -0.0004(9) -0.0005(10) C60 0.0333(13) 0.0364(14) 0.0387(13) 0.0033(11) 0.0113(10) 0.0012(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 N1 C28 1.362(3) . ? N1 C24 1.368(3) . ? N1 C23 1.489(2) . ? N2 C54 1.358(3) . ? N2 C58 1.368(3) . ? N2 C53 1.490(2) . ? B1 O1 1.514(2) . ? B1 C1 1.643(3) . ? B1 C7 1.645(3) . ? B1 C13 1.654(3) . ? B2 O3 1.511(2) . ? B2 C43 1.645(3) . ? B2 C37 1.651(3) . ? B2 C31 1.652(3) . ? F1 C10 1.344(2) . ? F2 C16 1.347(2) . ? F3 C14 1.350(2) . ? F4 C15 1.345(2) . ? F5 C12 1.353(2) . ? F6 C8 1.352(2) . ? F7 C9 1.348(2) . ? F8 C11 1.345(2) . ? F9 C6 1.358(2) . ? F10 C5 1.345(3) . ? F11 C4 1.346(3) . ? F12 C2 1.350(2) . ? F13 C3 1.343(3) . ? F14 C18 1.355(2) . ? F15 C17 1.350(2) . ? F32 C32 1.354(2) . ? F33 C33 1.342(2) . ? F34 C34 1.344(2) . ? F35 C35 1.346(2) . ? F36 C36 1.354(2) . ? F38 C38 1.356(2) . ? F39 C39 1.346(2) . ? F40 C40 1.340(2) . ? F41 C41 1.350(2) . ? F42 C42 1.356(2) . ? F44 C44 1.353(2) . ? F45 C45 1.348(2) . ? F46 C46 1.345(2) . ? F47 C47 1.347(2) . ? F48 C48 1.353(2) . ? O1 C19 1.321(2) . ? O1S C1S 1.350(4) . ? O1S C4S 1.411(3) . ? O2S C5S 1.420(3) . ? O2S C8S 1.437(3) . ? O2 C19 1.216(2) . ? O3 C49 1.320(2) . ? O4 C49 1.218(2) . ? C1 C6 1.388(3) . ? C1 C2 1.390(3) . ? C1S C2S 1.409(5) . ? C1S H1SA 0.9900 . ? C1S H1SB 0.9900 . ? C2 C3 1.381(3) . ? C2S C3S 1.505(4) . ? C2S H2SA 0.9900 . ? C2S H2SB 0.9900 . ? C3 C4 1.366(3) . ? C3S C4S 1.499(4) . ? C3S H3SA 0.9900 . ? C3S H3SB 0.9900 . ? C4 C5 1.373(3) . ? C4S H4SA 0.9900 . ? C4S H4SB 0.9900 . ? C5S C6S 1.516(3) . ? C5S H5SA 0.9900 . ? C5S H5SB 0.9900 . ? C5 C6 1.378(3) . ? C6S C7S 1.516(4) . ? C6S H6SA 0.9900 . ? C6S H6SB 0.9900 . ? C7S C8S 1.509(3) . ? C7S H7SA 0.9900 . ? C7S H7SB 0.9900 . ? C7 C12 1.386(3) . ? C7 C8 1.388(3) . ? C8S H8SA 0.9900 . ? C8S H8SB 0.9900 . ? C8 C9 1.378(3) . ? C9 C10 1.374(3) . ? C10 C11 1.372(3) . ? C11 C12 1.378(3) . ? C13 C18 1.380(3) . ? C13 C14 1.392(3) . ? C14 C15 1.381(3) . ? C15 C16 1.373(3) . ? C16 C17 1.369(3) . ? C17 C18 1.379(3) . ? C19 C20 1.509(3) . ? C20 C21 1.526(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.527(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.523(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.372(3) . ? C24 C30 1.490(3) . ? C25 C26 1.365(4) . ? C25 H25A 0.9500 . ? C26 C27 1.371(4) . ? C26 H26A 0.9500 . ? C27 C28 1.391(3) . ? C27 H27A 0.9500 . ? C28 C29 1.484(3) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 C36 1.385(3) . ? C31 C32 1.389(3) . ? C32 C33 1.380(3) . ? C33 C34 1.367(3) . ? C34 C35 1.374(3) . ? C35 C36 1.381(3) . ? C37 C42 1.390(3) . ? C37 C38 1.392(3) . ? C38 C39 1.379(3) . ? C39 C40 1.367(3) . ? C40 C41 1.368(3) . ? C41 C42 1.379(3) . ? C43 C44 1.388(3) . ? C43 C48 1.391(3) . ? C44 C45 1.378(3) . ? C45 C46 1.369(3) . ? C46 C47 1.373(3) . ? C47 C48 1.373(3) . ? C49 C50 1.511(3) . ? C50 C51 1.521(3) . ? C50 H50A 0.9900 . ? C50 H50B 0.9900 . ? C51 C52 1.527(3) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C52 C53 1.522(3) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C54 C55 1.382(3) . ? C54 C59 1.498(3) . ? C55 C56 1.377(3) . ? C55 H55A 0.9500 . ? C56 C57 1.372(3) . ? C56 H56A 0.9500 . ? C57 C58 1.378(3) . ? C57 H57A 0.9500 . ? C58 C60 1.495(3) . ? C59 H59A 0.9800 . ? C59 H59B 0.9800 . ? C59 H59C 0.9800 . ? C60 H60A 0.9800 . ? C60 H60B 0.9800 . ? C60 H60C 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 C28 N1 C24 122.03(18) . . ? C28 N1 C23 119.42(17) . . ? C24 N1 C23 118.54(17) . . ? C54 N2 C58 121.89(16) . . ? C54 N2 C53 119.12(16) . . ? C58 N2 C53 118.97(17) . . ? O1 B1 C1 112.58(15) . . ? O1 B1 C7 106.21(15) . . ? C1 B1 C7 115.75(16) . . ? O1 B1 C13 104.35(15) . . ? C1 B1 C13 104.12(15) . . ? C7 B1 C13 113.39(15) . . ? O3 B2 C43 106.18(15) . . ? O3 B2 C37 105.34(15) . . ? C43 B2 C37 114.14(16) . . ? O3 B2 C31 113.68(16) . . ? C43 B2 C31 113.21(16) . . ? C37 B2 C31 104.21(15) . . ? C19 O1 B1 121.05(15) . . ? C1S O1S C4S 107.5(2) . . ? C5S O2S C8S 109.67(17) . . ? C49 O3 B2 121.67(15) . . ? C6 C1 C2 113.34(19) . . ? C6 C1 B1 119.31(17) . . ? C2 C1 B1 126.94(18) . . ? O1S C1S C2S 113.8(3) . . ? O1S C1S H1SA 108.8 . . ? C2S C1S H1SA 108.8 . . ? O1S C1S H1SB 108.8 . . ? C2S C1S H1SB 108.8 . . ? H1SA C1S H1SB 107.7 . . ? F12 C2 C3 114.92(18) . . ? F12 C2 C1 121.35(19) . . ? C3 C2 C1 123.7(2) . . ? C1S C2S C3S 103.6(3) . . ? C1S C2S H2SA 111.0 . . ? C3S C2S H2SA 111.0 . . ? C1S C2S H2SB 111.0 . . ? C3S C2S H2SB 111.0 . . ? H2SA C2S H2SB 109.0 . . ? F13 C3 C4 119.7(2) . . ? F13 C3 C2 120.4(2) . . ? C4 C3 C2 119.9(2) . . ? C4S C3S C2S 102.6(2) . . ? C4S C3S H3SA 111.2 . . ? C2S C3S H3SA 111.2 . . ? C4S C3S H3SB 111.2 . . ? C2S C3S H3SB 111.2 . . ? H3SA C3S H3SB 109.2 . . ? F11 C4 C3 120.8(2) . . ? F11 C4 C5 119.9(2) . . ? C3 C4 C5 119.3(2) . . ? O1S C4S C3S 107.5(2) . . ? O1S C4S H4SA 110.2 . . ? C3S C4S H4SA 110.2 . . ? O1S C4S H4SB 110.2 . . ? C3S C4S H4SB 110.2 . . ? H4SA C4S H4SB 108.5 . . ? O2S C5S C6S 106.8(2) . . ? O2S C5S H5SA 110.4 . . ? C6S C5S H5SA 110.4 . . ? O2S C5S H5SB 110.4 . . ? C6S C5S H5SB 110.4 . . ? H5SA C5S H5SB 108.6 . . ? F10 C5 C4 120.3(2) . . ? F10 C5 C6 120.7(2) . . ? C4 C5 C6 119.0(2) . . ? C7S C6S C5S 101.70(19) . . ? C7S C6S H6SA 111.4 . . ? C5S C6S H6SA 111.4 . . ? C7S C6S H6SB 111.4 . . ? C5S C6S H6SB 111.4 . . ? H6SA C6S H6SB 109.3 . . ? F9 C6 C5 116.56(19) . . ? F9 C6 C1 118.74(18) . . ? C5 C6 C1 124.7(2) . . ? C8S C7S C6S 102.5(2) . . ? C8S C7S H7SA 111.3 . . ? C6S C7S H7SA 111.3 . . ? C8S C7S H7SB 111.3 . . ? C6S C7S H7SB 111.3 . . ? H7SA C7S H7SB 109.2 . . ? C12 C7 C8 113.10(18) . . ? C12 C7 B1 120.10(17) . . ? C8 C7 B1 126.47(18) . . ? O2S C8S C7S 105.9(2) . . ? O2S C8S H8SA 110.6 . . ? C7S C8S H8SA 110.6 . . ? O2S C8S H8SB 110.6 . . ? C7S C8S H8SB 110.6 . . ? H8SA C8S H8SB 108.7 . . ? F6 C8 C9 115.09(17) . . ? F6 C8 C7 120.81(18) . . ? C9 C8 C7 124.09(19) . . ? F7 C9 C10 119.59(18) . . ? F7 C9 C8 120.64(18) . . ? C10 C9 C8 119.77(18) . . ? F1 C10 C11 120.22(19) . . ? F1 C10 C9 120.73(18) . . ? C11 C10 C9 119.04(19) . . ? F8 C11 C10 119.90(18) . . ? F8 C11 C12 121.05(18) . . ? C10 C11 C12 119.02(19) . . ? F5 C12 C11 115.47(17) . . ? F5 C12 C7 119.58(17) . . ? C11 C12 C7 124.95(18) . . ? C18 C13 C14 113.05(17) . . ? C18 C13 B1 126.98(17) . . ? C14 C13 B1 119.91(17) . . ? F3 C14 C15 116.29(18) . . ? F3 C14 C13 119.39(17) . . ? C15 C14 C13 124.27(18) . . ? F4 C15 C16 119.68(18) . . ? F4 C15 C14 120.89(19) . . ? C16 C15 C14 119.42(19) . . ? F2 C16 C17 120.85(19) . . ? F2 C16 C15 120.1(2) . . ? C17 C16 C15 118.98(18) . . ? F15 C17 C16 120.43(17) . . ? F15 C17 C18 120.05(19) . . ? C16 C17 C18 119.51(18) . . ? F14 C18 C17 114.71(17) . . ? F14 C18 C13 120.56(16) . . ? C17 C18 C13 124.72(19) . . ? O2 C19 O1 124.68(17) . . ? O2 C19 C20 122.93(17) . . ? O1 C19 C20 112.37(16) . . ? C19 C20 C21 112.80(16) . . ? C19 C20 H20A 109.0 . . ? C21 C20 H20A 109.0 . . ? C19 C20 H20B 109.0 . . ? C21 C20 H20B 109.0 . . ? H20A C20 H20B 107.8 . . ? C20 C21 C22 111.82(16) . . ? C20 C21 H21A 109.3 . . ? C22 C21 H21A 109.3 . . ? C20 C21 H21B 109.3 . . ? C22 C21 H21B 109.3 . . ? H21A C21 H21B 107.9 . . ? C23 C22 C21 110.58(16) . . ? C23 C22 H22A 109.5 . . ? C21 C22 H22A 109.5 . . ? C23 C22 H22B 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 108.1 . . ? N1 C23 C22 111.82(16) . . ? N1 C23 H23A 109.3 . . ? C22 C23 H23A 109.3 . . ? N1 C23 H23B 109.3 . . ? C22 C23 H23B 109.3 . . ? H23A C23 H23B 107.9 . . ? N1 C24 C25 119.0(2) . . ? N1 C24 C30 120.60(19) . . ? C25 C24 C30 120.4(2) . . ? C26 C25 C24 120.6(2) . . ? C26 C25 H25A 119.7 . . ? C24 C25 H25A 119.7 . . ? C25 C26 C27 119.6(2) . . ? C25 C26 H26A 120.2 . . ? C27 C26 H26A 120.2 . . ? C26 C27 C28 120.8(2) . . ? C26 C27 H27A 119.6 . . ? C28 C27 H27A 119.6 . . ? N1 C28 C27 118.0(2) . . ? N1 C28 C29 120.22(19) . . ? C27 C28 C29 121.8(2) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C24 C30 H30A 109.5 . . ? C24 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C24 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C36 C31 C32 113.11(17) . . ? C36 C31 B2 126.09(17) . . ? C32 C31 B2 120.73(17) . . ? F32 C32 C33 115.52(17) . . ? F32 C32 C31 119.32(17) . . ? C33 C32 C31 125.12(19) . . ? F33 C33 C34 120.54(18) . . ? F33 C33 C32 120.58(19) . . ? C34 C33 C32 118.88(18) . . ? F34 C34 C33 121.32(19) . . ? F34 C34 C35 119.81(19) . . ? C33 C34 C35 118.87(18) . . ? F35 C35 C34 119.18(18) . . ? F35 C35 C36 120.52(18) . . ? C34 C35 C36 120.30(19) . . ? F36 C36 C35 115.34(18) . . ? F36 C36 C31 121.08(17) . . ? C35 C36 C31 123.58(18) . . ? C42 C37 C38 112.42(18) . . ? C42 C37 B2 125.62(17) . . ? C38 C37 B2 121.72(17) . . ? F38 C38 C39 115.13(18) . . ? F38 C38 C37 120.04(18) . . ? C39 C38 C37 124.83(19) . . ? F39 C39 C40 119.86(19) . . ? F39 C39 C38 120.47(19) . . ? C40 C39 C38 119.67(19) . . ? F40 C40 C39 120.83(19) . . ? F40 C40 C41 120.6(2) . . ? C39 C40 C41 118.58(19) . . ? F41 C41 C40 119.55(19) . . ? F41 C41 C42 120.31(19) . . ? C40 C41 C42 120.11(19) . . ? F42 C42 C41 115.23(18) . . ? F42 C42 C37 120.39(18) . . ? C41 C42 C37 124.39(19) . . ? C44 C43 C48 112.92(18) . . ? C44 C43 B2 126.39(17) . . ? C48 C43 B2 120.55(17) . . ? F44 C44 C45 114.64(18) . . ? F44 C44 C43 121.00(18) . . ? C45 C44 C43 124.35(19) . . ? F45 C45 C46 119.57(19) . . ? F45 C45 C44 120.69(19) . . ? C46 C45 C44 119.7(2) . . ? F46 C46 C45 120.4(2) . . ? F46 C46 C47 120.8(2) . . ? C45 C46 C47 118.8(2) . . ? F47 C47 C48 120.7(2) . . ? F47 C47 C46 119.6(2) . . ? C48 C47 C46 119.66(19) . . ? F48 C48 C47 115.99(18) . . ? F48 C48 C43 119.55(18) . . ? C47 C48 C43 124.46(19) . . ? O4 C49 O3 124.43(17) . . ? O4 C49 C50 123.37(18) . . ? O3 C49 C50 112.19(16) . . ? C49 C50 C51 112.76(16) . . ? C49 C50 H50A 109.0 . . ? C51 C50 H50A 109.0 . . ? C49 C50 H50B 109.0 . . ? C51 C50 H50B 109.0 . . ? H50A C50 H50B 107.8 . . ? C50 C51 C52 113.57(16) . . ? C50 C51 H51A 108.9 . . ? C52 C51 H51A 108.9 . . ? C50 C51 H51B 108.9 . . ? C52 C51 H51B 108.9 . . ? H51A C51 H51B 107.7 . . ? C53 C52 C51 109.17(16) . . ? C53 C52 H52A 109.8 . . ? C51 C52 H52A 109.8 . . ? C53 C52 H52B 109.8 . . ? C51 C52 H52B 109.8 . . ? H52A C52 H52B 108.3 . . ? N2 C53 C52 111.80(15) . . ? N2 C53 H53A 109.3 . . ? C52 C53 H53A 109.3 . . ? N2 C53 H53B 109.3 . . ? C52 C53 H53B 109.3 . . ? H53A C53 H53B 107.9 . . ? N2 C54 C55 119.08(19) . . ? N2 C54 C59 120.22(17) . . ? C55 C54 C59 120.67(19) . . ? C56 C55 C54 120.3(2) . . ? C56 C55 H55A 119.9 . . ? C54 C55 H55A 119.9 . . ? C57 C56 C55 119.24(19) . . ? C57 C56 H56A 120.4 . . ? C55 C56 H56A 120.4 . . ? C56 C57 C58 120.9(2) . . ? C56 C57 H57A 119.5 . . ? C58 C57 H57A 119.5 . . ? N2 C58 C57 118.52(19) . . ? N2 C58 C60 119.92(18) . . ? C57 C58 C60 121.5(2) . . ? C54 C59 H59A 109.5 . . ? C54 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? C54 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? C58 C60 H60A 109.5 . . ? C58 C60 H60B 109.5 . . ? H60A C60 H60B 109.5 . . ? C58 C60 H60C 109.5 . . ? H60A C60 H60C 109.5 . . ? H60B C60 H60C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.792 _refine_diff_density_min -0.807 _refine_diff_density_rms 0.054 # Attachment '- 5-CK002_0m.cif' data_ck002_0m _database_code_depnum_ccdc_archive 'CCDC 817781' #TrackingRef '- 5-CK002_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H27 B F15 N O3' _chemical_formula_weight 805.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 10.5600(5) _cell_length_b 12.7148(6) _cell_length_c 14.0599(7) _cell_angle_alpha 73.412(2) _cell_angle_beta 69.794(2) _cell_angle_gamma 80.586(2) _cell_volume 1693.45(14) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7545 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 26.72 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.579 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.155 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6892 _exptl_absorpt_correction_T_max 0.7456 _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28231 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 27.54 _reflns_number_total 7793 _reflns_number_gt 5426 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0455P)^2^+0.8903P] 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 7793 _refine_ls_number_parameters 496 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0725 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1133 _refine_ls_wR_factor_gt 0.0996 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 0.8281(2) 0.31902(17) 0.32670(16) 0.0206(4) Uani 1 1 d . . . N1 N 1.02721(16) 0.79486(13) 0.27702(12) 0.0254(4) Uani 1 1 d . . . O1 O 0.76979(12) 0.41763(10) 0.37174(9) 0.0223(3) Uani 1 1 d . . . O1S O 0.4233(3) 0.8381(3) 0.1876(3) 0.1338(14) Uani 1 1 d . . . O2 O 0.81173(14) 0.34474(11) 0.52395(11) 0.0316(3) Uani 1 1 d . . . F2 F 0.54051(11) 0.30237(9) 0.38441(9) 0.0320(3) Uani 1 1 d . . . F3 F 0.39076(11) 0.14764(10) 0.53303(10) 0.0387(3) Uani 1 1 d . . . F4 F 0.50861(13) -0.02579(10) 0.64557(10) 0.0423(3) Uani 1 1 d . . . F5 F 0.78181(13) -0.04269(11) 0.60280(11) 0.0501(4) Uani 1 1 d . . . F6 F 0.93306(11) 0.10940(10) 0.45767(9) 0.0379(3) Uani 1 1 d . . . F8 F 1.03597(11) 0.45188(9) 0.34303(9) 0.0321(3) Uani 1 1 d . . . F9 F 1.30166(11) 0.41912(10) 0.26683(9) 0.0361(3) Uani 1 1 d . . . F10 F 1.41536(12) 0.24944(12) 0.17551(10) 0.0454(3) Uani 1 1 d . . . F11 F 1.25196(12) 0.11433(10) 0.15883(10) 0.0401(3) Uani 1 1 d . . . F12 F 0.98385(11) 0.14677(9) 0.23306(9) 0.0296(3) Uani 1 1 d . . . F14 F 0.70844(11) 0.18806(9) 0.22979(8) 0.0301(3) Uani 1 1 d . . . F15 F 0.68324(12) 0.25348(10) 0.04005(9) 0.0362(3) Uani 1 1 d . . . F16 F 0.75249(14) 0.45514(11) -0.08358(9) 0.0451(3) Uani 1 1 d . . . F17 F 0.85936(13) 0.59064(10) -0.01541(9) 0.0407(3) Uani 1 1 d . . . F18 F 0.89544(12) 0.52476(9) 0.17133(9) 0.0313(3) Uani 1 1 d . . . C1 C 0.74557(18) 0.21399(15) 0.41098(14) 0.0212(4) Uani 1 1 d . . . C1S C 0.4967(4) 0.7640(3) 0.2561(3) 0.0850(11) Uani 1 1 d . . . H1SA H 0.5655 0.8026 0.2638 0.102 Uiso 1 1 calc R . . H1SB H 0.4340 0.7327 0.3262 0.102 Uiso 1 1 calc R . . C2 C 0.60585(18) 0.21767(15) 0.43635(14) 0.0233(4) Uani 1 1 d . . . C2S C 0.5594(5) 0.6797(4) 0.2001(3) 0.1016(14) Uani 1 1 d . . . H2SA H 0.6544 0.6615 0.1996 0.122 Uiso 1 1 calc R . . H2SB H 0.5100 0.6120 0.2343 0.122 Uiso 1 1 calc R . . C3 C 0.52615(19) 0.13880(16) 0.51314(15) 0.0269(4) Uani 1 1 d . . . C3S C 0.5544(5) 0.7223(4) 0.0947(3) 0.1059(14) Uani 1 1 d . . . H3SA H 0.6471 0.7279 0.0443 0.127 Uiso 1 1 calc R . . H3SB H 0.5063 0.6731 0.0776 0.127 Uiso 1 1 calc R . . C4 C 0.5846(2) 0.05069(16) 0.56993(15) 0.0290(4) Uani 1 1 d . . . C4S C 0.4841(5) 0.8282(4) 0.0896(4) 0.1021(14) Uani 1 1 d . . . H4SA H 0.5483 0.8861 0.0501 0.122 Uiso 1 1 calc R . . H4SB H 0.4161 0.8361 0.0537 0.122 Uiso 1 1 calc R . . C5 C 0.7226(2) 0.04256(16) 0.54781(15) 0.0303(5) Uani 1 1 d . . . C6 C 0.79901(19) 0.12343(16) 0.47036(15) 0.0257(4) Uani 1 1 d . . . C7 C 0.99412(18) 0.29951(15) 0.29417(13) 0.0214(4) Uani 1 1 d . . . C8 C 1.08277(19) 0.36498(15) 0.29975(14) 0.0232(4) Uani 1 1 d . . . C9 C 1.22224(19) 0.34955(17) 0.26105(15) 0.0269(4) Uani 1 1 d . . . C10 C 1.28052(19) 0.26555(18) 0.21359(15) 0.0301(5) Uani 1 1 d . . . C11 C 1.1973(2) 0.19799(16) 0.20508(15) 0.0274(4) Uani 1 1 d . . . C12 C 1.05967(19) 0.21655(15) 0.24449(14) 0.0234(4) Uani 1 1 d . . . C13 C 0.79889(17) 0.35439(15) 0.21322(14) 0.0213(4) Uani 1 1 d . . . C14 C 0.74670(18) 0.28981(15) 0.17332(14) 0.0236(4) Uani 1 1 d . . . C15 C 0.73119(19) 0.32195(17) 0.07523(15) 0.0268(4) Uani 1 1 d . . . C16 C 0.7671(2) 0.42357(17) 0.01217(15) 0.0297(4) Uani 1 1 d . . . C17 C 0.8204(2) 0.49138(16) 0.04677(15) 0.0284(4) Uani 1 1 d . . . C18 C 0.83617(18) 0.45586(15) 0.14476(14) 0.0240(4) Uani 1 1 d . . . C19 C 0.75972(18) 0.41712(16) 0.46778(14) 0.0237(4) Uani 1 1 d . . . C20 C 0.67878(19) 0.51649(16) 0.50256(15) 0.0270(4) Uani 1 1 d . . . H20A H 0.6205 0.4933 0.5761 0.032 Uiso 1 1 calc R . . H20B H 0.6194 0.5498 0.4589 0.032 Uiso 1 1 calc R . . C21 C 0.77099(19) 0.60220(16) 0.49367(14) 0.0247(4) Uani 1 1 d . . . H21A H 0.7173 0.6549 0.5351 0.030 Uiso 1 1 calc R . . H21B H 0.8428 0.5648 0.5244 0.030 Uiso 1 1 calc R . . C22 C 0.83709(19) 0.66594(16) 0.38117(14) 0.0237(4) Uani 1 1 d . . . H22A H 0.8924 0.6146 0.3388 0.028 Uiso 1 1 calc R . . H22B H 0.7667 0.7054 0.3496 0.028 Uiso 1 1 calc R . . C23 C 0.92584(19) 0.74749(16) 0.38292(14) 0.0254(4) Uani 1 1 d . . . H23A H 0.9760 0.7106 0.4328 0.031 Uiso 1 1 calc R . . H23B H 0.8670 0.8089 0.4093 0.031 Uiso 1 1 calc R . . C24 C 1.1356(2) 0.70612(17) 0.24867(17) 0.0324(5) Uani 1 1 d . . . H24A H 1.2018 0.7355 0.1808 0.049 Uiso 1 1 calc R . . H24B H 1.0947 0.6444 0.2445 0.049 Uiso 1 1 calc R . . H24C H 1.1809 0.6806 0.3022 0.049 Uiso 1 1 calc R . . C25 C 1.0960(2) 0.88272(18) 0.29015(18) 0.0348(5) Uani 1 1 d . . . H25A H 1.1623 0.9146 0.2232 0.052 Uiso 1 1 calc R . . H25B H 1.1420 0.8500 0.3426 0.052 Uiso 1 1 calc R . . H25C H 1.0281 0.9405 0.3131 0.052 Uiso 1 1 calc R . . C26 C 0.9576(2) 0.84327(16) 0.19559(15) 0.0268(4) Uani 1 1 d . . . C27 C 0.8600(2) 0.92928(17) 0.21046(17) 0.0348(5) Uani 1 1 d . . . H27A H 0.8379 0.9566 0.2709 0.042 Uiso 1 1 calc R . . C28 C 0.7946(3) 0.97514(19) 0.13616(19) 0.0425(6) Uani 1 1 d . . . H28A H 0.7269 1.0338 0.1460 0.051 Uiso 1 1 calc R . . C29 C 0.8280(3) 0.9357(2) 0.04785(18) 0.0430(6) Uani 1 1 d . . . H29A H 0.7848 0.9684 -0.0038 0.052 Uiso 1 1 calc R . . C30 C 0.9233(3) 0.8494(2) 0.03508(18) 0.0466(6) Uani 1 1 d . . . H30A H 0.9447 0.8214 -0.0249 0.056 Uiso 1 1 calc R . . C31 C 0.9888(2) 0.8024(2) 0.10907(17) 0.0379(5) Uani 1 1 d . . . H31A H 1.0548 0.7425 0.1000 0.046 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 0.0230(10) 0.0175(10) 0.0194(10) -0.0027(8) -0.0063(8) -0.0003(8) N1 0.0270(8) 0.0235(9) 0.0244(8) -0.0063(7) -0.0051(7) -0.0042(7) O1 0.0264(7) 0.0194(7) 0.0193(6) -0.0045(5) -0.0055(5) -0.0008(5) O1S 0.0787(19) 0.089(2) 0.173(3) -0.040(2) 0.031(2) 0.0173(16) O2 0.0401(8) 0.0293(8) 0.0266(7) -0.0053(6) -0.0147(6) 0.0008(6) F2 0.0243(6) 0.0275(6) 0.0357(7) -0.0001(5) -0.0077(5) 0.0037(5) F3 0.0227(6) 0.0369(7) 0.0459(7) -0.0057(6) -0.0002(5) -0.0050(5) F4 0.0437(7) 0.0347(7) 0.0346(7) 0.0062(6) -0.0008(6) -0.0166(6) F5 0.0450(8) 0.0388(8) 0.0469(8) 0.0221(6) -0.0168(6) -0.0029(6) F6 0.0269(6) 0.0380(7) 0.0366(7) 0.0112(5) -0.0119(5) -0.0018(5) F8 0.0320(6) 0.0295(6) 0.0392(7) -0.0138(5) -0.0120(5) -0.0033(5) F9 0.0306(6) 0.0486(8) 0.0301(6) -0.0037(6) -0.0101(5) -0.0157(5) F10 0.0212(6) 0.0653(9) 0.0416(7) -0.0136(7) -0.0010(5) -0.0006(6) F11 0.0352(7) 0.0380(7) 0.0405(7) -0.0169(6) -0.0026(6) 0.0078(6) F12 0.0316(6) 0.0230(6) 0.0333(6) -0.0092(5) -0.0074(5) -0.0021(5) F14 0.0390(6) 0.0255(6) 0.0255(6) -0.0037(5) -0.0089(5) -0.0094(5) F15 0.0387(7) 0.0472(8) 0.0286(6) -0.0138(6) -0.0123(5) -0.0077(6) F16 0.0617(9) 0.0515(8) 0.0215(6) -0.0008(6) -0.0194(6) -0.0034(7) F17 0.0541(8) 0.0299(7) 0.0267(6) 0.0078(5) -0.0094(6) -0.0056(6) F18 0.0404(7) 0.0245(6) 0.0272(6) -0.0015(5) -0.0093(5) -0.0092(5) C1 0.0257(9) 0.0197(9) 0.0169(9) -0.0052(7) -0.0047(7) -0.0017(7) C1S 0.084(3) 0.092(3) 0.073(2) -0.038(2) -0.006(2) 0.001(2) C2 0.0255(9) 0.0195(10) 0.0226(9) -0.0048(8) -0.0061(8) 0.0005(7) C2S 0.122(3) 0.109(3) 0.066(2) -0.041(2) -0.023(2) 0.033(3) C3 0.0231(9) 0.0278(11) 0.0275(10) -0.0095(9) -0.0025(8) -0.0030(8) C3S 0.136(4) 0.118(4) 0.078(3) -0.044(3) -0.048(3) 0.016(3) C4 0.0337(11) 0.0253(11) 0.0208(10) -0.0007(8) 0.0003(8) -0.0111(9) C4S 0.120(4) 0.092(3) 0.125(4) -0.026(3) -0.078(3) -0.008(3) C5 0.0366(11) 0.0234(11) 0.0250(10) 0.0034(8) -0.0105(9) -0.0011(9) C6 0.0239(9) 0.0260(10) 0.0233(10) -0.0019(8) -0.0065(8) -0.0007(8) C7 0.0244(9) 0.0199(9) 0.0157(9) 0.0011(7) -0.0055(7) -0.0019(7) C8 0.0269(9) 0.0207(10) 0.0195(9) -0.0016(8) -0.0075(8) -0.0012(8) C9 0.0272(10) 0.0315(11) 0.0200(9) 0.0026(8) -0.0087(8) -0.0093(8) C10 0.0200(9) 0.0401(12) 0.0207(10) 0.0004(9) -0.0020(8) -0.0005(8) C11 0.0299(10) 0.0251(10) 0.0207(10) -0.0038(8) -0.0040(8) 0.0036(8) C12 0.0269(9) 0.0202(10) 0.0195(9) 0.0003(7) -0.0062(8) -0.0040(8) C13 0.0200(8) 0.0208(9) 0.0197(9) -0.0041(7) -0.0042(7) 0.0013(7) C14 0.0224(9) 0.0218(10) 0.0215(9) -0.0020(8) -0.0033(7) -0.0020(7) C15 0.0242(9) 0.0345(11) 0.0228(10) -0.0114(9) -0.0067(8) 0.0005(8) C16 0.0314(10) 0.0368(12) 0.0164(9) -0.0028(8) -0.0082(8) 0.0037(9) C17 0.0317(10) 0.0238(10) 0.0205(10) 0.0022(8) -0.0042(8) 0.0009(8) C18 0.0244(9) 0.0219(10) 0.0225(9) -0.0051(8) -0.0043(8) -0.0001(8) C19 0.0235(9) 0.0237(10) 0.0218(10) -0.0038(8) -0.0040(8) -0.0064(8) C20 0.0247(9) 0.0285(11) 0.0238(10) -0.0079(8) -0.0014(8) -0.0027(8) C21 0.0265(9) 0.0250(10) 0.0212(9) -0.0071(8) -0.0050(8) -0.0009(8) C22 0.0248(9) 0.0235(10) 0.0215(9) -0.0059(8) -0.0054(7) -0.0016(8) C23 0.0271(10) 0.0274(10) 0.0204(9) -0.0084(8) -0.0042(8) -0.0011(8) C24 0.0274(10) 0.0309(11) 0.0332(11) -0.0099(9) -0.0023(9) 0.0008(9) C25 0.0379(11) 0.0311(12) 0.0388(12) -0.0082(10) -0.0128(10) -0.0106(9) C26 0.0316(10) 0.0252(10) 0.0228(10) -0.0026(8) -0.0069(8) -0.0096(8) C27 0.0477(13) 0.0276(11) 0.0339(12) -0.0082(9) -0.0180(10) -0.0034(10) C28 0.0556(14) 0.0289(12) 0.0497(15) -0.0049(11) -0.0293(12) -0.0022(10) C29 0.0526(14) 0.0471(15) 0.0332(12) 0.0028(11) -0.0215(11) -0.0196(12) C30 0.0498(14) 0.0657(18) 0.0279(12) -0.0161(12) -0.0093(10) -0.0129(13) C31 0.0365(12) 0.0487(14) 0.0301(12) -0.0166(10) -0.0062(9) -0.0045(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 B1 O1 1.511(2) . ? B1 C1 1.647(3) . ? B1 C7 1.647(3) . ? B1 C13 1.652(3) . ? N1 C26 1.504(2) . ? N1 C24 1.504(3) . ? N1 C25 1.512(2) . ? N1 C23 1.524(2) . ? O1 C19 1.315(2) . ? O1S C4S 1.337(5) . ? O1S C1S 1.475(5) . ? O2 C19 1.221(2) . ? F2 C2 1.351(2) . ? F3 C3 1.351(2) . ? F4 C4 1.340(2) . ? F5 C5 1.341(2) . ? F6 C6 1.352(2) . ? F8 C8 1.354(2) . ? F9 C9 1.350(2) . ? F10 C10 1.340(2) . ? F11 C11 1.350(2) . ? F12 C12 1.363(2) . ? F14 C14 1.353(2) . ? F15 C15 1.350(2) . ? F16 C16 1.346(2) . ? F17 C17 1.348(2) . ? F18 C18 1.351(2) . ? C1 C6 1.380(3) . ? C1 C2 1.389(3) . ? C1S C2S 1.448(5) . ? C1S H1SA 0.9900 . ? C1S H1SB 0.9900 . ? C2 C3 1.382(3) . ? C2S C3S 1.442(5) . ? C2S H2SA 0.9900 . ? C2S H2SB 0.9900 . ? C3 C4 1.370(3) . ? C3S C4S 1.423(6) . ? C3S H3SA 0.9900 . ? C3S H3SB 0.9900 . ? C4 C5 1.373(3) . ? C4S H4SA 0.9900 . ? C4S H4SB 0.9900 . ? C5 C6 1.386(3) . ? C7 C8 1.385(3) . ? C7 C12 1.388(3) . ? C8 C9 1.384(3) . ? C9 C10 1.369(3) . ? C10 C11 1.379(3) . ? C11 C12 1.372(3) . ? C13 C14 1.385(3) . ? C13 C18 1.393(3) . ? C14 C15 1.381(3) . ? C15 C16 1.369(3) . ? C16 C17 1.373(3) . ? C17 C18 1.381(3) . ? C19 C20 1.509(3) . ? C20 C21 1.529(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.529(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.517(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? 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 C31 1.373(3) . ? C26 C27 1.384(3) . ? C27 C28 1.388(3) . ? C27 H27A 0.9500 . ? C28 C29 1.383(3) . ? C28 H28A 0.9500 . ? C29 C30 1.370(4) . ? C29 H29A 0.9500 . ? C30 C31 1.387(3) . ? C30 H30A 0.9500 . ? C31 H31A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 B1 C1 106.13(14) . . ? O1 B1 C7 114.29(15) . . ? C1 B1 C7 114.88(15) . . ? O1 B1 C13 103.50(14) . . ? C1 B1 C13 113.95(15) . . ? C7 B1 C13 103.70(14) . . ? C26 N1 C24 112.94(15) . . ? C26 N1 C25 110.21(15) . . ? C24 N1 C25 106.40(15) . . ? C26 N1 C23 110.97(14) . . ? C24 N1 C23 108.55(15) . . ? C25 N1 C23 107.53(15) . . ? C19 O1 B1 122.32(14) . . ? C4S O1S C1S 109.1(3) . . ? C6 C1 C2 113.62(16) . . ? C6 C1 B1 126.37(16) . . ? C2 C1 B1 119.62(16) . . ? C2S C1S O1S 102.2(3) . . ? C2S C1S H1SA 111.3 . . ? O1S C1S H1SA 111.3 . . ? C2S C1S H1SB 111.3 . . ? O1S C1S H1SB 111.3 . . ? H1SA C1S H1SB 109.2 . . ? F2 C2 C3 116.29(16) . . ? F2 C2 C1 119.70(16) . . ? C3 C2 C1 124.02(17) . . ? C3S C2S C1S 107.5(4) . . ? C3S C2S H2SA 110.2 . . ? C1S C2S H2SA 110.2 . . ? C3S C2S H2SB 110.2 . . ? C1S C2S H2SB 110.2 . . ? H2SA C2S H2SB 108.5 . . ? F3 C3 C4 119.47(17) . . ? F3 C3 C2 120.66(17) . . ? C4 C3 C2 119.88(18) . . ? C4S C3S C2S 106.9(4) . . ? C4S C3S H3SA 110.3 . . ? C2S C3S H3SA 110.3 . . ? C4S C3S H3SB 110.3 . . ? C2S C3S H3SB 110.3 . . ? H3SA C3S H3SB 108.6 . . ? F4 C4 C3 120.64(18) . . ? F4 C4 C5 120.76(18) . . ? C3 C4 C5 118.60(17) . . ? O1S C4S C3S 107.8(4) . . ? O1S C4S H4SA 110.1 . . ? C3S C4S H4SA 110.1 . . ? O1S C4S H4SB 110.1 . . ? C3S C4S H4SB 110.1 . . ? H4SA C4S H4SB 108.5 . . ? F5 C5 C4 119.60(17) . . ? F5 C5 C6 120.58(18) . . ? C4 C5 C6 119.81(18) . . ? F6 C6 C1 121.01(16) . . ? F6 C6 C5 114.91(16) . . ? C1 C6 C5 124.06(18) . . ? C8 C7 C12 112.92(17) . . ? C8 C7 B1 127.38(17) . . ? C12 C7 B1 119.30(16) . . ? F8 C8 C9 115.16(16) . . ? F8 C8 C7 120.78(16) . . ? C9 C8 C7 124.05(18) . . ? F9 C9 C10 119.49(17) . . ? F9 C9 C8 120.38(18) . . ? C10 C9 C8 120.10(18) . . ? F10 C10 C9 120.95(19) . . ? F10 C10 C11 120.54(19) . . ? C9 C10 C11 118.51(17) . . ? F11 C11 C12 120.85(18) . . ? F11 C11 C10 119.83(17) . . ? C12 C11 C10 119.32(19) . . ? F12 C12 C11 116.09(17) . . ? F12 C12 C7 118.81(16) . . ? C11 C12 C7 125.10(18) . . ? C14 C13 C18 113.83(16) . . ? C14 C13 B1 126.56(16) . . ? C18 C13 B1 119.48(16) . . ? F14 C14 C15 115.35(17) . . ? F14 C14 C13 120.78(16) . . ? C15 C14 C13 123.86(17) . . ? F15 C15 C16 119.54(17) . . ? F15 C15 C14 120.74(17) . . ? C16 C15 C14 119.70(18) . . ? F16 C16 C15 119.93(18) . . ? F16 C16 C17 120.71(18) . . ? C15 C16 C17 119.35(17) . . ? F17 C17 C16 120.08(17) . . ? F17 C17 C18 120.59(18) . . ? C16 C17 C18 119.32(18) . . ? F18 C18 C17 115.92(16) . . ? F18 C18 C13 120.13(16) . . ? C17 C18 C13 123.91(18) . . ? O2 C19 O1 124.08(18) . . ? O2 C19 C20 122.41(17) . . ? O1 C19 C20 113.50(16) . . ? C19 C20 C21 111.38(15) . . ? C19 C20 H20A 109.4 . . ? C21 C20 H20A 109.4 . . ? C19 C20 H20B 109.4 . . ? C21 C20 H20B 109.4 . . ? H20A C20 H20B 108.0 . . ? C22 C21 C20 113.48(15) . . ? C22 C21 H21A 108.9 . . ? C20 C21 H21A 108.9 . . ? C22 C21 H21B 108.9 . . ? C20 C21 H21B 108.9 . . ? H21A C21 H21B 107.7 . . ? C23 C22 C21 108.33(15) . . ? C23 C22 H22A 110.0 . . ? C21 C22 H22A 110.0 . . ? C23 C22 H22B 110.0 . . ? C21 C22 H22B 110.0 . . ? H22A C22 H22B 108.4 . . ? C22 C23 N1 114.40(15) . . ? C22 C23 H23A 108.7 . . ? N1 C23 H23A 108.7 . . ? C22 C23 H23B 108.7 . . ? N1 C23 H23B 108.7 . . ? H23A C23 H23B 107.6 . . ? N1 C24 H24A 109.5 . . ? N1 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N1 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N1 C25 H25A 109.5 . . ? N1 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N1 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C31 C26 C27 120.67(19) . . ? C31 C26 N1 120.91(19) . . ? C27 C26 N1 118.41(17) . . ? C26 C27 C28 119.3(2) . . ? C26 C27 H27A 120.4 . . ? C28 C27 H27A 120.4 . . ? C29 C28 C27 120.1(2) . . ? C29 C28 H28A 119.9 . . ? C27 C28 H28A 119.9 . . ? C30 C29 C28 119.9(2) . . ? C30 C29 H29A 120.1 . . ? C28 C29 H29A 120.1 . . ? C29 C30 C31 120.5(2) . . ? C29 C30 H30A 119.7 . . ? C31 C30 H30A 119.7 . . ? C26 C31 C30 119.5(2) . . ? C26 C31 H31A 120.3 . . ? C30 C31 H31A 120.3 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.597 _refine_diff_density_min -0.444 _refine_diff_density_rms 0.051 # Attachment '- 6-ck005_0m.cif' data_ck005_0m _database_code_depnum_ccdc_archive 'CCDC 817782' #TrackingRef '- 6-ck005_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35.50 H26 B F15 N O2' _chemical_formula_weight 794.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _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 11.4886(8) _cell_length_b 14.9489(11) _cell_length_c 20.7973(15) _cell_angle_alpha 90.00 _cell_angle_beta 104.278(3) _cell_angle_gamma 90.00 _cell_volume 3461.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9131 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 25.11 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.524 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1608 _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6966 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 49430 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0464 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 27.51 _reflns_number_total 7929 _reflns_number_gt 5029 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0664P)^2^+1.2478P] 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 7929 _refine_ls_number_parameters 520 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0930 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1389 _refine_ls_wR_factor_gt 0.1198 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 F15 F 0.01678(11) 0.12370(9) 0.23480(6) 0.0340(3) Uani 1 1 d . . . F11 F -0.29728(10) 0.05051(8) 0.04687(6) 0.0299(3) Uani 1 1 d . . . F14 F 0.16756(11) 0.13862(9) 0.15683(7) 0.0377(3) Uani 1 1 d . . . F10 F -0.03900(11) -0.05596(9) 0.22779(6) 0.0366(3) Uani 1 1 d . . . O2 O -0.40469(13) -0.05717(10) 0.13642(7) 0.0293(3) Uani 1 1 d . . . F13 F 0.08723(12) 0.11660(10) 0.02274(7) 0.0408(3) Uani 1 1 d . . . F12 F -0.14707(12) 0.06825(9) -0.02941(6) 0.0379(3) Uani 1 1 d . . . O1 O -0.36963(12) 0.08758(9) 0.16010(7) 0.0246(3) Uani 1 1 d . . . F6 F -0.38457(12) 0.05408(10) 0.28784(7) 0.0436(4) Uani 1 1 d . . . F9 F -0.01300(13) -0.17820(11) 0.32090(8) 0.0534(4) Uani 1 1 d . . . F1 F -0.32241(14) 0.25018(9) 0.12210(8) 0.0497(4) Uani 1 1 d . . . N1 N -0.59016(15) 0.23482(12) -0.08373(8) 0.0249(4) Uani 1 1 d . . . C1 C -0.43982(18) 0.01960(14) 0.13860(10) 0.0233(4) Uani 1 1 d . . . F8 F -0.16914(15) -0.18771(11) 0.40095(7) 0.0568(4) Uani 1 1 d . . . C29 C -0.10574(19) 0.08240(14) 0.03621(10) 0.0263(5) Uani 1 1 d . . . F7 F -0.35607(15) -0.07142(11) 0.38147(8) 0.0562(4) Uani 1 1 d . . . C28 C -0.18273(18) 0.07335(14) 0.07784(10) 0.0234(4) Uani 1 1 d . . . C26 C -0.11984(18) -0.05365(16) 0.26505(11) 0.0293(5) Uani 1 1 d . . . C27 C -0.14901(17) 0.08665(13) 0.14544(10) 0.0228(4) Uani 1 1 d . . . C31 C 0.05154(18) 0.11810(15) 0.12973(11) 0.0276(5) Uani 1 1 d . . . C3 C -0.59699(18) 0.13852(15) 0.08795(10) 0.0269(5) Uani 1 1 d . . . H3A H -0.6806 0.1557 0.0870 0.032 Uiso 1 1 calc R . . H3B H -0.5426 0.1828 0.1155 0.032 Uiso 1 1 calc R . . B1 B -0.2380(2) 0.08845(16) 0.19649(12) 0.0236(5) Uani 1 1 d . . . C4 C -0.57996(19) 0.14062(15) 0.01750(10) 0.0275(5) Uani 1 1 d . . . H4A H -0.4997 0.1164 0.0176 0.033 Uiso 1 1 calc R . . H4B H -0.6410 0.1019 -0.0113 0.033 Uiso 1 1 calc R . . C2 C -0.57092(18) 0.04564(15) 0.11949(11) 0.0283(5) Uani 1 1 d . . . H2A H -0.6024 0.0435 0.1597 0.034 Uiso 1 1 calc R . . H2B H -0.6154 0.0006 0.0879 0.034 Uiso 1 1 calc R . . C21 C -0.21211(18) 0.00887(15) 0.25290(10) 0.0256(5) Uani 1 1 d . . . C13 C -0.4556(2) 0.37425(16) -0.07632(13) 0.0402(6) Uani 1 1 d . . . H13A H -0.3815 0.3967 -0.0859 0.060 Uiso 1 1 calc R . . H13B H -0.4500 0.3796 -0.0287 0.060 Uiso 1 1 calc R . . H13C H -0.5240 0.4094 -0.1012 0.060 Uiso 1 1 calc R . . F4 F -0.10254(16) 0.31937(15) 0.37898(10) 0.0903(8) Uani 1 1 d . . . C32 C -0.02809(18) 0.10911(15) 0.16884(10) 0.0261(5) Uani 1 1 d . . . C11 C -0.4805(2) 0.26254(16) -0.17069(11) 0.0337(5) Uani 1 1 d . . . H11A H -0.4100 0.2916 -0.1812 0.040 Uiso 1 1 calc R . . H11B H -0.4755 0.1977 -0.1794 0.040 Uiso 1 1 calc R . . C9 C -0.7031(2) 0.25500(16) -0.20125(11) 0.0336(5) Uani 1 1 d . . . H9A H -0.7765 0.2798 -0.2313 0.040 Uiso 1 1 calc R . . H9B H -0.7007 0.1902 -0.2107 0.040 Uiso 1 1 calc R . . C22 C -0.2890(2) -0.00178(16) 0.29459(11) 0.0316(5) Uani 1 1 d . . . C25 C -0.1036(2) -0.11874(17) 0.31390(12) 0.0360(6) Uani 1 1 d . . . C30 C 0.01176(19) 0.10563(15) 0.06240(11) 0.0292(5) Uani 1 1 d . . . C5 C -0.5911(2) 0.23473(15) -0.01042(10) 0.0285(5) Uani 1 1 d . . . H5A H -0.5236 0.2716 0.0148 0.034 Uiso 1 1 calc R . . H5B H -0.6669 0.2619 -0.0052 0.034 Uiso 1 1 calc R . . C16 C -0.2711(2) 0.26283(17) 0.18758(15) 0.0417(6) Uani 1 1 d . . . F2 F -0.31639(19) 0.41669(11) 0.16683(13) 0.0939(7) Uani 1 1 d . . . C6 C -0.71190(19) 0.26703(15) -0.12992(11) 0.0292(5) Uani 1 1 d . . . C15 C -0.22482(19) 0.19132(16) 0.22773(11) 0.0316(5) Uani 1 1 d . . . C14 C -0.3692(2) 0.21984(17) -0.05667(12) 0.0367(6) Uani 1 1 d . . . H14A H -0.2932 0.2427 -0.0636 0.055 Uiso 1 1 calc R . . H14B H -0.3797 0.1574 -0.0712 0.055 Uiso 1 1 calc R . . H14C H -0.3680 0.2236 -0.0095 0.055 Uiso 1 1 calc R . . C12 C -0.47333(19) 0.27597(15) -0.09697(11) 0.0293(5) Uani 1 1 d . . . C20 C -0.1686(2) 0.21535(19) 0.29210(13) 0.0415(6) Uani 1 1 d . . . C10 C -0.5937(2) 0.29958(18) -0.21687(12) 0.0378(6) Uani 1 1 d . . . H10A H -0.5927 0.2877 -0.2636 0.045 Uiso 1 1 calc R . . H10B H -0.5976 0.3651 -0.2109 0.045 Uiso 1 1 calc R . . C23 C -0.2767(2) -0.06542(17) 0.34354(12) 0.0375(6) Uani 1 1 d . . . F3 F -0.20684(18) 0.45503(12) 0.29607(14) 0.1063(9) Uani 1 1 d . . . C24 C -0.1824(2) -0.12480(17) 0.35346(12) 0.0393(6) Uani 1 1 d . . . C7 C -0.8092(2) 0.20408(18) -0.11747(12) 0.0372(6) Uani 1 1 d . . . H7A H -0.8874 0.2217 -0.1457 0.056 Uiso 1 1 calc R . . H7B H -0.8115 0.2077 -0.0708 0.056 Uiso 1 1 calc R . . H7C H -0.7910 0.1426 -0.1280 0.056 Uiso 1 1 calc R . . C8 C -0.7420(2) 0.36345(17) -0.11618(13) 0.0415(6) Uani 1 1 d . . . H8A H -0.8188 0.3803 -0.1463 0.062 Uiso 1 1 calc R . . H8B H -0.6785 0.4032 -0.1233 0.062 Uiso 1 1 calc R . . H8C H -0.7481 0.3687 -0.0702 0.062 Uiso 1 1 calc R . . C19 C -0.1605(3) 0.3025(2) 0.31541(17) 0.0615(10) Uani 1 1 d . . . C17 C -0.2678(3) 0.35041(18) 0.2092(2) 0.0599(9) Uani 1 1 d . . . C18 C -0.2123(3) 0.3706(2) 0.2736(2) 0.0693(11) Uani 1 1 d . . . C100 C 0.0000 0.0000 0.5000 0.0928(19) Uani 1 2 d S . . C101 C 0.0491(6) 0.0194(5) 0.4541(3) 0.0576(16) Uani 0.50 1 d P . . C102 C 0.1177(6) -0.0464(5) 0.4350(4) 0.0620(17) Uani 0.50 1 d P . . F5 F -0.11606(14) 0.15284(12) 0.33688(7) 0.0565(4) Uani 1 1 d . . . C103 C 0.1261(6) -0.1299(6) 0.4636(3) 0.0679(19) Uani 0.50 1 d P . . C104 C 0.0996(8) -0.0660(10) 0.4842(5) 0.110(4) Uani 0.50 1 d P . . C105 C 0.0055(7) 0.0868(6) 0.4708(4) 0.074(2) Uani 0.50 1 d P . . C107 C 0.0706(7) -0.1497(6) 0.5078(4) 0.076(2) Uani 0.50 1 d P . . 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 F15 0.0237(6) 0.0476(8) 0.0299(7) -0.0119(6) 0.0051(5) -0.0068(6) F11 0.0235(6) 0.0366(8) 0.0275(6) 0.0006(5) 0.0028(5) -0.0058(5) F14 0.0209(6) 0.0477(9) 0.0460(8) -0.0067(6) 0.0110(6) -0.0089(6) F10 0.0271(7) 0.0411(8) 0.0448(8) 0.0060(6) 0.0152(6) 0.0092(6) O2 0.0319(8) 0.0233(9) 0.0318(8) 0.0004(7) 0.0063(7) -0.0016(7) F13 0.0357(7) 0.0507(9) 0.0431(8) 0.0045(7) 0.0233(6) -0.0044(6) F12 0.0398(7) 0.0498(9) 0.0247(7) 0.0048(6) 0.0089(6) -0.0006(6) O1 0.0192(7) 0.0223(8) 0.0320(8) 0.0005(6) 0.0056(6) -0.0002(6) F6 0.0445(8) 0.0442(9) 0.0516(9) 0.0081(7) 0.0297(7) 0.0180(7) F9 0.0430(9) 0.0545(10) 0.0629(10) 0.0213(8) 0.0132(7) 0.0239(8) F1 0.0479(9) 0.0317(8) 0.0668(11) 0.0141(7) 0.0091(8) -0.0001(7) N1 0.0200(9) 0.0260(10) 0.0279(9) 0.0054(8) 0.0046(7) 0.0002(7) C1 0.0252(10) 0.0249(12) 0.0212(10) 0.0024(9) 0.0081(8) -0.0038(9) F8 0.0681(10) 0.0568(10) 0.0482(9) 0.0249(8) 0.0193(8) 0.0140(8) C29 0.0305(12) 0.0255(12) 0.0231(11) 0.0027(9) 0.0069(9) 0.0013(9) F7 0.0701(11) 0.0584(10) 0.0548(9) 0.0128(8) 0.0431(8) 0.0115(8) C28 0.0192(10) 0.0199(11) 0.0297(11) 0.0014(9) 0.0034(8) -0.0016(8) C26 0.0221(11) 0.0362(13) 0.0291(12) -0.0014(10) 0.0055(9) 0.0005(10) C27 0.0212(10) 0.0192(11) 0.0285(11) -0.0024(9) 0.0073(8) -0.0017(8) C31 0.0191(10) 0.0264(12) 0.0367(13) -0.0011(10) 0.0059(9) -0.0024(9) C3 0.0192(10) 0.0319(13) 0.0306(11) 0.0035(9) 0.0082(9) 0.0021(9) B1 0.0181(11) 0.0248(13) 0.0280(12) -0.0047(10) 0.0061(9) -0.0002(10) C4 0.0279(11) 0.0251(12) 0.0295(12) 0.0010(9) 0.0073(9) 0.0000(9) C2 0.0208(10) 0.0329(13) 0.0317(12) 0.0041(10) 0.0073(9) -0.0036(9) C21 0.0224(10) 0.0290(12) 0.0246(11) -0.0052(9) 0.0041(9) -0.0003(9) C13 0.0415(14) 0.0324(14) 0.0459(15) 0.0007(11) 0.0097(11) -0.0109(11) F4 0.0643(12) 0.1187(18) 0.0988(14) -0.0862(14) 0.0409(11) -0.0406(11) C32 0.0236(11) 0.0270(12) 0.0275(12) -0.0055(9) 0.0060(9) -0.0022(9) C11 0.0322(12) 0.0332(13) 0.0391(13) 0.0045(10) 0.0152(10) -0.0041(10) C9 0.0331(12) 0.0324(13) 0.0328(13) 0.0071(10) 0.0031(10) 0.0020(10) C22 0.0305(12) 0.0319(13) 0.0337(12) 0.0000(10) 0.0104(10) 0.0091(10) C25 0.0306(12) 0.0381(14) 0.0363(13) 0.0034(11) 0.0027(10) 0.0098(11) C30 0.0277(12) 0.0275(12) 0.0368(13) 0.0044(10) 0.0161(10) 0.0000(9) C5 0.0301(12) 0.0273(12) 0.0286(12) 0.0008(9) 0.0081(9) -0.0007(9) C16 0.0309(13) 0.0278(14) 0.0705(19) -0.0051(13) 0.0202(13) -0.0046(11) F2 0.0848(14) 0.0239(9) 0.183(2) 0.0122(12) 0.0520(15) 0.0046(9) C6 0.0230(11) 0.0296(13) 0.0334(12) 0.0064(10) 0.0036(9) 0.0043(9) C15 0.0214(11) 0.0323(13) 0.0446(14) -0.0111(11) 0.0148(10) -0.0044(10) C14 0.0241(11) 0.0413(15) 0.0434(14) 0.0065(11) 0.0059(10) -0.0044(10) C12 0.0230(11) 0.0273(12) 0.0373(13) 0.0039(10) 0.0069(9) -0.0045(9) C20 0.0281(12) 0.0473(16) 0.0531(16) -0.0219(14) 0.0178(12) -0.0067(12) C10 0.0406(14) 0.0405(15) 0.0323(13) 0.0096(11) 0.0087(11) -0.0010(11) C23 0.0441(14) 0.0382(14) 0.0360(13) 0.0004(11) 0.0211(11) 0.0037(12) F3 0.0852(14) 0.0485(12) 0.213(3) -0.0762(14) 0.0901(16) -0.0322(10) C24 0.0473(15) 0.0380(15) 0.0310(13) 0.0084(11) 0.0065(11) 0.0043(12) C7 0.0243(12) 0.0453(15) 0.0414(14) 0.0040(11) 0.0071(10) 0.0000(11) C8 0.0395(14) 0.0342(14) 0.0507(16) 0.0082(12) 0.0112(12) 0.0130(11) C19 0.0382(15) 0.070(2) 0.088(2) -0.057(2) 0.0375(16) -0.0264(16) C17 0.0466(16) 0.0224(15) 0.121(3) -0.0085(17) 0.0411(18) -0.0040(13) C18 0.0474(18) 0.0381(18) 0.139(3) -0.046(2) 0.055(2) -0.0186(15) C100 0.081(4) 0.133(6) 0.055(3) -0.012(4) -0.001(3) -0.001(4) C101 0.047(4) 0.066(5) 0.059(4) 0.015(4) 0.012(3) -0.003(3) C102 0.065(4) 0.062(5) 0.058(4) 0.008(3) 0.013(3) -0.008(3) F5 0.0517(9) 0.0757(12) 0.0386(8) -0.0219(8) 0.0045(7) -0.0082(9) C103 0.055(4) 0.079(5) 0.056(4) 0.010(4) -0.013(3) -0.020(4) C104 0.072(6) 0.159(11) 0.089(7) -0.050(8) 0.001(5) 0.041(7) C105 0.062(5) 0.094(6) 0.060(4) 0.036(4) 0.003(4) -0.010(5) C107 0.061(4) 0.085(6) 0.075(5) 0.016(4) 0.005(4) 0.004(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 F15 C32 1.359(2) . ? F11 C28 1.358(2) . ? F14 C31 1.348(2) . ? F10 C26 1.349(2) . ? O2 C1 1.221(3) . ? F13 C30 1.346(2) . ? F12 C29 1.346(2) . ? O1 C1 1.306(2) . ? O1 B1 1.515(3) . ? F6 C22 1.359(2) . ? F9 C25 1.349(3) . ? F1 C16 1.357(3) . ? N1 C5 1.527(3) . ? N1 C12 1.561(3) . ? N1 C6 1.565(3) . ? C1 C2 1.511(3) . ? F8 C24 1.345(3) . ? C29 C30 1.370(3) . ? C29 C28 1.389(3) . ? F7 C23 1.348(3) . ? C28 C27 1.377(3) . ? C26 C25 1.386(3) . ? C26 C21 1.389(3) . ? C27 C32 1.395(3) . ? C27 B1 1.646(3) . ? C31 C32 1.372(3) . ? C31 C30 1.374(3) . ? C3 C4 1.525(3) . ? C3 C2 1.533(3) . ? B1 C21 1.646(3) . ? B1 C15 1.662(3) . ? C4 C5 1.515(3) . ? C21 C22 1.391(3) . ? C13 C12 1.530(3) . ? F4 C19 1.349(4) . ? C11 C10 1.518(3) . ? C11 C12 1.528(3) . ? C9 C6 1.522(3) . ? C9 C10 1.526(3) . ? C22 C23 1.375(3) . ? C25 C24 1.369(3) . ? C16 C15 1.380(4) . ? C16 C17 1.382(4) . ? F2 C17 1.352(4) . ? C6 C8 1.526(3) . ? C6 C7 1.531(3) . ? C15 C20 1.383(3) . ? C14 C12 1.531(3) . ? C20 F5 1.352(3) . ? C20 C19 1.385(4) . ? C23 C24 1.376(3) . ? F3 C18 1.342(3) . ? C19 C18 1.375(5) . ? C17 C18 1.367(5) . ? C100 C101 1.257(6) . ? C100 C101 1.257(6) 3_556 ? C100 C105 1.441(8) . ? C100 C105 1.441(8) 3_556 ? C100 C104 1.604(9) 3_556 ? C100 C104 1.604(9) . ? C101 C105 1.213(11) . ? C101 C102 1.378(11) . ? C101 C104 1.476(15) . ? C102 C104 1.132(12) . ? C102 C103 1.376(10) . ? C103 C104 1.121(11) . ? C103 C107 1.277(11) . ? C104 C107 1.414(16) . ? C104 C105 1.728(14) 3_556 ? C105 C107 1.427(12) 3_556 ? C105 C104 1.728(14) 3_556 ? C107 C105 1.427(12) 3_556 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 B1 129.34(17) . . ? C5 N1 C12 113.23(16) . . ? C5 N1 C6 112.81(16) . . ? C12 N1 C6 116.59(15) . . ? O2 C1 O1 124.21(19) . . ? O2 C1 C2 123.34(19) . . ? O1 C1 C2 112.39(18) . . ? F12 C29 C30 120.63(18) . . ? F12 C29 C28 119.80(19) . . ? C30 C29 C28 119.56(19) . . ? F11 C28 C27 121.06(17) . . ? F11 C28 C29 114.86(17) . . ? C27 C28 C29 124.08(19) . . ? F10 C26 C25 114.56(19) . . ? F10 C26 C21 121.03(19) . . ? C25 C26 C21 124.4(2) . . ? C28 C27 C32 113.34(17) . . ? C28 C27 B1 126.69(18) . . ? C32 C27 B1 119.65(18) . . ? F14 C31 C32 120.62(19) . . ? F14 C31 C30 120.19(18) . . ? C32 C31 C30 119.20(19) . . ? C4 C3 C2 111.82(18) . . ? O1 B1 C21 109.44(16) . . ? O1 B1 C27 112.33(17) . . ? C21 B1 C27 114.58(17) . . ? O1 B1 C15 100.78(16) . . ? C21 B1 C15 114.03(18) . . ? C27 B1 C15 104.83(17) . . ? C5 C4 C3 111.62(18) . . ? C1 C2 C3 115.01(17) . . ? C26 C21 C22 112.52(19) . . ? C26 C21 B1 127.74(18) . . ? C22 C21 B1 119.73(18) . . ? F15 C32 C31 116.12(18) . . ? F15 C32 C27 119.22(17) . . ? C31 C32 C27 124.66(19) . . ? C10 C11 C12 114.35(19) . . ? C6 C9 C10 114.33(19) . . ? F6 C22 C23 115.74(19) . . ? F6 C22 C21 119.11(19) . . ? C23 C22 C21 125.2(2) . . ? F9 C25 C24 119.9(2) . . ? F9 C25 C26 120.2(2) . . ? C24 C25 C26 119.8(2) . . ? F13 C30 C29 120.5(2) . . ? F13 C30 C31 120.35(19) . . ? C29 C30 C31 119.15(18) . . ? C4 C5 N1 111.27(17) . . ? F1 C16 C15 120.4(2) . . ? F1 C16 C17 115.4(3) . . ? C15 C16 C17 124.2(3) . . ? C9 C6 C8 111.51(19) . . ? C9 C6 C7 108.60(19) . . ? C8 C6 C7 109.89(19) . . ? C9 C6 N1 107.32(17) . . ? C8 C6 N1 112.67(19) . . ? C7 C6 N1 106.65(17) . . ? C16 C15 C20 113.8(2) . . ? C16 C15 B1 119.7(2) . . ? C20 C15 B1 126.5(2) . . ? C11 C12 C13 112.23(19) . . ? C11 C12 C14 108.57(19) . . ? C13 C12 C14 109.93(19) . . ? C11 C12 N1 106.82(17) . . ? C13 C12 N1 112.90(18) . . ? C14 C12 N1 106.10(17) . . ? F5 C20 C15 120.7(2) . . ? F5 C20 C19 115.4(3) . . ? C15 C20 C19 123.9(3) . . ? C11 C10 C9 109.15(18) . . ? F7 C23 C22 121.3(2) . . ? F7 C23 C24 119.4(2) . . ? C22 C23 C24 119.4(2) . . ? F8 C24 C25 121.0(2) . . ? F8 C24 C23 120.3(2) . . ? C25 C24 C23 118.7(2) . . ? F4 C19 C18 120.9(3) . . ? F4 C19 C20 119.5(4) . . ? C18 C19 C20 119.6(3) . . ? F2 C17 C18 119.7(3) . . ? F2 C17 C16 120.5(3) . . ? C18 C17 C16 119.8(3) . . ? F3 C18 C17 121.3(4) . . ? F3 C18 C19 120.0(4) . . ? C17 C18 C19 118.7(3) . . ? C101 C100 C101 180.0(5) . 3_556 ? C101 C100 C105 52.9(4) . . ? C101 C100 C105 127.1(4) 3_556 . ? C101 C100 C105 127.1(4) . 3_556 ? C101 C100 C105 52.9(4) 3_556 3_556 ? C105 C100 C105 179.999(1) . 3_556 ? C101 C100 C104 119.3(6) . 3_556 ? C101 C100 C104 60.7(6) 3_556 3_556 ? C105 C100 C104 68.9(7) . 3_556 ? C105 C100 C104 111.1(7) 3_556 3_556 ? C101 C100 C104 60.7(6) . . ? C101 C100 C104 119.3(6) 3_556 . ? C105 C100 C104 111.1(7) . . ? C105 C100 C104 68.9(7) 3_556 . ? C104 C100 C104 179.999(3) 3_556 . ? C105 C101 C100 71.3(5) . . ? C105 C101 C102 168.7(7) . . ? C100 C101 C102 116.7(6) . . ? C105 C101 C104 138.0(8) . . ? C100 C101 C104 71.4(5) . . ? C102 C101 C104 46.6(5) . . ? C104 C102 C103 52.0(7) . . ? C104 C102 C101 71.3(8) . . ? C103 C102 C101 120.6(7) . . ? C104 C103 C107 71.9(10) . . ? C104 C103 C102 52.7(8) . . ? C107 C103 C102 121.7(9) . . ? C103 C104 C102 75.3(8) . . ? C103 C104 C107 59.2(9) . . ? C102 C104 C107 130.9(11) . . ? C103 C104 C101 133.7(11) . . ? C102 C104 C101 62.2(9) . . ? C107 C104 C101 144.2(8) . . ? C103 C104 C100 151.4(10) . . ? C102 C104 C100 109.0(10) . . ? C107 C104 C100 103.4(8) . . ? C101 C104 C100 47.9(4) . . ? C103 C104 C105 110.2(13) . 3_556 ? C102 C104 C105 147.6(8) . 3_556 ? C107 C104 C105 52.9(7) . 3_556 ? C101 C104 C105 97.6(6) . 3_556 ? C100 C104 C105 51.1(4) . 3_556 ? C101 C105 C107 164.5(8) . 3_556 ? C101 C105 C100 55.8(5) . . ? C107 C105 C100 111.6(6) 3_556 . ? C101 C105 C104 113.5(8) . 3_556 ? C107 C105 C104 52.2(6) 3_556 3_556 ? C100 C105 C104 60.0(5) . 3_556 ? C103 C107 C104 48.9(5) . . ? C103 C107 C105 121.7(8) . 3_556 ? C104 C107 C105 74.9(7) . 3_556 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.692 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.054 # Attachment '- 8-ls008_0m.cif' data_ls008_0m _database_code_depnum_ccdc_archive 'CCDC 817783' #TrackingRef '- 8-ls008_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H35 B F15 O4 P' _chemical_formula_weight 858.42 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 10.026(2) _cell_length_b 12.823(3) _cell_length_c 14.762(3) _cell_angle_alpha 90.192(8) _cell_angle_beta 102.530(8) _cell_angle_gamma 94.474(7) _cell_volume 1846.5(7) _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 ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 876 _exptl_absorpt_coefficient_mu 0.190 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9594 _exptl_absorpt_correction_T_max 0.9812 _exptl_absorpt_process_details sadads _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 29856 _diffrn_reflns_av_R_equivalents 0.1260 _diffrn_reflns_av_sigmaI/netI 0.2394 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.62 _reflns_number_total 8407 _reflns_number_gt 2662 _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^)+(0.0917P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8407 _refine_ls_number_parameters 518 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2735 _refine_ls_R_factor_gt 0.0812 _refine_ls_wR_factor_ref 0.2325 _refine_ls_wR_factor_gt 0.1650 _refine_ls_goodness_of_fit_ref 0.943 _refine_ls_restrained_S_all 0.943 _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 P1 P 0.35637(16) 0.12603(11) 0.22532(10) 0.0433(4) Uani 1 1 d . . . F10 F 0.1791(4) 0.6606(3) -0.1218(2) 0.0878(12) Uani 1 1 d . . . F16 F -0.0123(8) 0.3385(3) 0.4647(4) 0.191(3) Uani 1 1 d . . . F17 F -0.1720(7) 0.4131(4) 0.3064(4) 0.149(3) Uani 1 1 d . . . F18 F -0.0716(4) 0.5725(3) 0.2184(3) 0.0771(12) Uani 1 1 d . . . F15 F 0.2439(7) 0.4317(4) 0.5323(4) 0.166(3) Uani 1 1 d . . . F12 F 0.1553(4) 0.4923(2) 0.1536(2) 0.0667(10) Uani 1 1 d . . . F11 F 0.1577(4) 0.4826(3) -0.0235(2) 0.0750(11) Uani 1 1 d . . . F9 F 0.1938(4) 0.8503(3) -0.0343(2) 0.0802(11) Uani 1 1 d . . . F8 F 0.1904(3) 0.8630(2) 0.1437(2) 0.0535(9) Uani 1 1 d . . . F2 F 0.2043(3) 0.7800(2) 0.4568(2) 0.0554(9) Uani 1 1 d . . . F3 F 0.0247(3) 0.8886(2) 0.5149(2) 0.0611(10) Uani 1 1 d . . . F4 F -0.1982(3) 0.9493(3) 0.3928(3) 0.0756(11) Uani 1 1 d . . . F5 F -0.2322(3) 0.9018(3) 0.2101(3) 0.0852(12) Uani 1 1 d . . . F6 F -0.0669(3) 0.7809(3) 0.1513(2) 0.0624(10) Uani 1 1 d . . . F14 F 0.3429(5) 0.5886(3) 0.4465(3) 0.0967(15) Uani 1 1 d . . . C10 C 0.1755(6) 0.6663(6) -0.0315(4) 0.0623(18) Uani 1 1 d . . . C11 C 0.1676(6) 0.5780(5) 0.0190(5) 0.0571(17) Uani 1 1 d . . . C12 C 0.1672(6) 0.5856(5) 0.1110(4) 0.0493(15) Uani 1 1 d . . . C7 C 0.1761(5) 0.6787(4) 0.1612(4) 0.0423(14) Uani 1 1 d . . . B1 B 0.1886(7) 0.6932(5) 0.2734(4) 0.0414(16) Uani 1 1 d . . . C16 C 0.0320(17) 0.4185(7) 0.4185(10) 0.131(6) Uani 1 1 d . . . C17 C -0.0416(13) 0.4566(6) 0.3400(7) 0.106(4) Uani 1 1 d . . . C18 C 0.0111(9) 0.5363(5) 0.2959(5) 0.067(2) Uani 1 1 d . . . C13 C 0.1424(8) 0.5861(4) 0.3255(4) 0.0580(18) Uani 1 1 d . . . C14 C 0.2139(10) 0.5465(5) 0.4057(6) 0.077(2) Uani 1 1 d . . . C15 C 0.1617(14) 0.4625(7) 0.4509(7) 0.109(4) Uani 1 1 d . . . C9 C 0.1863(6) 0.7614(5) 0.0143(5) 0.0561(16) Uani 1 1 d . . . C8 C 0.1849(6) 0.7652(5) 0.1054(4) 0.0473(15) Uani 1 1 d . . . C1 C 0.0834(5) 0.7749(4) 0.3006(4) 0.0360(13) Uani 1 1 d . . . C2 C 0.0968(6) 0.8079(4) 0.3916(4) 0.0409(14) Uani 1 1 d . . . C3 C 0.0058(6) 0.8642(4) 0.4240(4) 0.0438(14) Uani 1 1 d . . . C4 C -0.1075(6) 0.8942(4) 0.3621(5) 0.0480(15) Uani 1 1 d . . . C5 C -0.1247(6) 0.8683(5) 0.2716(5) 0.0523(16) Uani 1 1 d . . . C6 C -0.0352(6) 0.8080(4) 0.2430(4) 0.0432(14) Uani 1 1 d . . . C26 C 0.4179(11) 0.2807(6) 0.1049(6) 0.143(4) Uani 1 1 d . . . H26A H 0.4198 0.2995 0.0409 0.215 Uiso 1 1 calc R . . H26B H 0.5109 0.2901 0.1435 0.215 Uiso 1 1 calc R . . H26C H 0.3584 0.3258 0.1290 0.215 Uiso 1 1 calc R . . C25 C 0.3623(10) 0.1659(6) 0.1070(5) 0.095(3) Uani 1 1 d . . . C33 C 0.5198(7) 0.1627(5) 0.3137(5) 0.076(2) Uani 1 1 d . . . C35 C 0.5232(9) 0.0854(5) 0.3949(5) 0.109(3) Uani 1 1 d . . . H35A H 0.6069 0.1018 0.4426 0.164 Uiso 1 1 calc R . . H35B H 0.5218 0.0136 0.3716 0.164 Uiso 1 1 calc R . . H35C H 0.4429 0.0921 0.4218 0.164 Uiso 1 1 calc R . . C36 C 0.5241(9) 0.2769(5) 0.3488(6) 0.122(3) Uani 1 1 d . . . H36A H 0.6098 0.2941 0.3945 0.182 Uiso 1 1 calc R . . H36B H 0.4461 0.2847 0.3777 0.182 Uiso 1 1 calc R . . H36C H 0.5191 0.3242 0.2964 0.182 Uiso 1 1 calc R . . C28 C 0.2209(12) 0.1414(8) 0.0432(6) 0.177(6) Uani 1 1 d . . . H28A H 0.2240 0.1627 -0.0200 0.266 Uiso 1 1 calc R . . H28B H 0.1532 0.1798 0.0656 0.266 Uiso 1 1 calc R . . H28C H 0.1951 0.0661 0.0433 0.266 Uiso 1 1 calc R . . C29 C 0.2006(8) 0.1581(5) 0.2626(7) 0.099(3) Uani 1 1 d . . . C32 C 0.0795(7) 0.0871(6) 0.2142(8) 0.157(5) Uani 1 1 d . . . H32A H -0.0027 0.1051 0.2346 0.236 Uiso 1 1 calc R . . H32B H 0.0964 0.0143 0.2293 0.236 Uiso 1 1 calc R . . H32C H 0.0658 0.0958 0.1469 0.236 Uiso 1 1 calc R . . C31 C 0.1718(8) 0.2759(5) 0.2402(7) 0.118(3) Uani 1 1 d . . . H31A H 0.0886 0.2922 0.2603 0.177 Uiso 1 1 calc R . . H31B H 0.1592 0.2863 0.1732 0.177 Uiso 1 1 calc R . . H31C H 0.2497 0.3223 0.2731 0.177 Uiso 1 1 calc R . . C30 C 0.2162(11) 0.1442(8) 0.3674(8) 0.160(5) Uani 1 1 d . . . H30A H 0.1321 0.1617 0.3856 0.241 Uiso 1 1 calc R . . H30B H 0.2937 0.1906 0.4008 0.241 Uiso 1 1 calc R . . H30C H 0.2329 0.0714 0.3829 0.241 Uiso 1 1 calc R . . C34 C 0.6454(7) 0.1452(6) 0.2715(7) 0.114(3) Uani 1 1 d . . . H34A H 0.7299 0.1644 0.3177 0.171 Uiso 1 1 calc R . . H34B H 0.6428 0.1888 0.2168 0.171 Uiso 1 1 calc R . . H34C H 0.6427 0.0714 0.2532 0.171 Uiso 1 1 calc R . . C27 C 0.4588(12) 0.0951(7) 0.0716(6) 0.143(4) Uani 1 1 d . . . H27A H 0.4643 0.1143 0.0083 0.214 Uiso 1 1 calc R . . H27B H 0.4228 0.0218 0.0718 0.214 Uiso 1 1 calc R . . H27C H 0.5504 0.1042 0.1122 0.214 Uiso 1 1 calc R . . O1 O 0.3270(4) 0.7407(3) 0.3159(2) 0.0457(10) Uani 1 1 d . . . O2 O 0.4188(5) 0.5255(3) 0.2802(3) 0.0725(13) Uani 1 1 d . . . O3 O 0.4720(4) 0.8748(3) 0.2002(3) 0.0738(14) Uani 1 1 d . . . O4 O 0.5539(6) 0.7297(4) 0.1611(4) 0.0997(17) Uani 1 1 d . . . C19 C 0.4492(6) 0.7177(4) 0.2937(4) 0.0559(17) Uani 1 1 d . . . C20 C 0.4658(7) 0.6076(6) 0.2589(5) 0.0683(19) Uani 1 1 d . . . C22 C 0.4877(6) 0.7854(5) 0.2157(5) 0.0597(18) Uani 1 1 d . . . C21 C 0.5651(11) 0.6227(6) 0.1948(7) 0.115(3) Uani 1 1 d . . . H21A H 0.6586 0.6231 0.2360 0.138 Uiso 1 1 calc R . . C23 C 0.5649(6) 0.7419(6) 0.3788(5) 0.082(2) Uani 1 1 d . . . H23A H 0.5461 0.7008 0.4311 0.123 Uiso 1 1 calc R . . H23B H 0.5712 0.8166 0.3948 0.123 Uiso 1 1 calc R . . H23C H 0.6518 0.7238 0.3651 0.123 Uiso 1 1 calc R . . C24 C 0.5649(13) 0.5554(7) 0.1254(8) 0.179(6) Uani 1 1 d . . . H24A H 0.6365 0.5793 0.0926 0.269 Uiso 1 1 calc R . . H24B H 0.4754 0.5515 0.0821 0.269 Uiso 1 1 calc R . . H24C H 0.5827 0.4860 0.1506 0.269 Uiso 1 1 calc R . . H1P H 0.356(4) 0.026(3) 0.230(3) 0.043(13) 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 P1 0.0459(10) 0.0323(9) 0.0546(10) 0.0031(7) 0.0142(8) 0.0112(7) F10 0.092(3) 0.121(3) 0.055(3) -0.016(2) 0.032(2) -0.005(2) F16 0.383(10) 0.042(3) 0.229(6) 0.040(3) 0.240(7) 0.033(4) F17 0.222(6) 0.082(3) 0.174(5) -0.065(3) 0.146(5) -0.086(4) F18 0.081(3) 0.080(3) 0.072(3) -0.027(2) 0.034(2) -0.035(2) F15 0.302(8) 0.126(4) 0.122(4) 0.084(3) 0.114(5) 0.144(5) F12 0.096(3) 0.041(2) 0.069(2) -0.0119(17) 0.031(2) 0.0030(18) F11 0.071(3) 0.084(3) 0.072(2) -0.036(2) 0.025(2) -0.005(2) F9 0.092(3) 0.094(3) 0.062(2) 0.021(2) 0.030(2) 0.010(2) F8 0.055(2) 0.050(2) 0.061(2) 0.0054(17) 0.0208(17) 0.0097(16) F2 0.062(2) 0.054(2) 0.0470(19) -0.0013(15) -0.0011(17) 0.0229(17) F3 0.086(3) 0.047(2) 0.058(2) -0.0048(16) 0.0289(19) 0.0161(18) F4 0.057(2) 0.076(3) 0.102(3) -0.010(2) 0.031(2) 0.022(2) F5 0.044(2) 0.114(3) 0.096(3) -0.004(2) 0.001(2) 0.035(2) F6 0.040(2) 0.092(3) 0.052(2) -0.0051(18) 0.0013(16) 0.0133(18) F14 0.126(4) 0.103(3) 0.072(3) 0.028(2) 0.023(3) 0.072(3) C10 0.056(4) 0.096(6) 0.039(4) -0.015(4) 0.024(3) -0.005(4) C11 0.049(4) 0.069(5) 0.056(5) -0.025(4) 0.020(3) -0.005(3) C12 0.044(4) 0.048(4) 0.059(4) 0.001(3) 0.020(3) 0.001(3) C7 0.038(4) 0.037(3) 0.054(4) -0.007(3) 0.017(3) 0.003(3) B1 0.041(4) 0.031(4) 0.054(4) -0.003(3) 0.014(3) 0.008(3) C16 0.253(17) 0.037(6) 0.159(12) 0.031(7) 0.160(14) 0.037(8) C17 0.192(11) 0.038(5) 0.116(8) -0.022(5) 0.112(8) -0.034(6) C18 0.108(7) 0.034(4) 0.074(5) -0.012(4) 0.055(5) -0.007(4) C13 0.099(6) 0.031(3) 0.052(4) 0.001(3) 0.029(4) 0.020(4) C14 0.115(7) 0.049(5) 0.086(6) 0.012(4) 0.051(6) 0.040(5) C15 0.213(12) 0.066(6) 0.087(7) 0.046(5) 0.098(9) 0.067(7) C9 0.052(4) 0.069(5) 0.052(4) 0.015(4) 0.021(3) 0.004(3) C8 0.044(4) 0.052(4) 0.048(4) -0.007(3) 0.016(3) 0.001(3) C1 0.030(3) 0.032(3) 0.047(4) 0.004(3) 0.010(3) 0.001(2) C2 0.044(4) 0.031(3) 0.047(4) -0.002(3) 0.008(3) 0.006(3) C3 0.054(4) 0.034(3) 0.048(4) 0.002(3) 0.021(3) 0.004(3) C4 0.035(4) 0.047(4) 0.071(5) 0.001(3) 0.027(3) 0.009(3) C5 0.032(4) 0.062(4) 0.062(4) -0.005(3) 0.007(3) 0.007(3) C6 0.041(4) 0.050(4) 0.039(4) -0.006(3) 0.011(3) 0.003(3) C26 0.244(13) 0.082(6) 0.129(8) 0.054(6) 0.087(8) 0.034(7) C25 0.156(8) 0.066(5) 0.071(5) 0.005(4) 0.031(6) 0.035(5) C33 0.077(5) 0.045(4) 0.100(6) -0.006(4) 0.012(4) -0.004(4) C35 0.143(8) 0.076(5) 0.086(6) 0.005(4) -0.030(5) 0.020(5) C36 0.122(7) 0.059(5) 0.154(8) -0.030(5) -0.035(6) 0.006(5) C28 0.241(14) 0.163(10) 0.094(7) -0.008(7) -0.068(8) 0.102(9) C29 0.081(6) 0.059(5) 0.179(9) -0.006(5) 0.075(6) 0.010(4) C32 0.036(5) 0.070(6) 0.363(16) -0.043(8) 0.041(7) -0.007(4) C31 0.077(6) 0.060(5) 0.232(10) -0.020(6) 0.059(6) 0.029(4) C30 0.186(11) 0.160(10) 0.189(11) 0.009(8) 0.155(10) 0.021(8) C34 0.051(5) 0.082(6) 0.206(10) 0.016(6) 0.019(6) 0.013(4) C27 0.248(13) 0.122(7) 0.088(7) 0.011(5) 0.087(8) 0.052(8) O1 0.033(2) 0.046(2) 0.059(2) -0.0074(18) 0.0059(19) 0.0187(18) O2 0.083(3) 0.047(3) 0.095(4) 0.011(3) 0.026(3) 0.033(3) O3 0.050(3) 0.049(3) 0.128(4) 0.007(3) 0.028(3) 0.012(2) O4 0.124(4) 0.064(3) 0.139(5) 0.018(3) 0.082(4) 0.026(3) C19 0.051(4) 0.042(4) 0.075(5) -0.003(3) 0.011(4) 0.016(3) C20 0.071(5) 0.058(5) 0.081(5) 0.007(4) 0.021(4) 0.023(4) C22 0.035(4) 0.056(4) 0.095(5) -0.005(4) 0.026(4) 0.015(3) C21 0.180(10) 0.062(6) 0.142(8) 0.017(5) 0.102(8) 0.052(6) C23 0.042(4) 0.103(6) 0.094(5) -0.017(4) -0.008(4) 0.028(4) C24 0.285(15) 0.080(7) 0.247(13) 0.032(7) 0.203(12) 0.061(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 P1 C25 1.833(7) . ? P1 C29 1.840(7) . ? P1 C33 1.885(7) . ? P1 H1P 1.28(4) . ? F10 C10 1.344(6) . ? F16 C16 1.334(10) . ? F17 C17 1.367(12) . ? F18 C18 1.365(8) . ? F15 C15 1.379(11) . ? F12 C12 1.363(6) . ? F11 C11 1.359(6) . ? F9 C9 1.355(7) . ? F8 C8 1.366(6) . ? F2 C2 1.353(6) . ? F3 C3 1.346(6) . ? F4 C4 1.345(6) . ? F5 C5 1.348(6) . ? F6 C6 1.359(6) . ? F14 C14 1.371(9) . ? C10 C11 1.364(9) . ? C10 C9 1.378(8) . ? C11 C12 1.363(8) . ? C12 C7 1.389(7) . ? C7 C8 1.394(7) . ? C7 B1 1.642(8) . ? B1 O1 1.476(7) . ? B1 C1 1.650(8) . ? B1 C13 1.660(9) . ? C16 C17 1.347(15) . ? C16 C15 1.361(15) . ? C17 C18 1.348(10) . ? C18 C13 1.396(9) . ? C13 C14 1.366(9) . ? C14 C15 1.396(11) . ? C9 C8 1.348(8) . ? C1 C2 1.381(7) . ? C1 C6 1.400(7) . ? C2 C3 1.368(7) . ? C3 C4 1.377(8) . ? C4 C5 1.346(7) . ? C5 C6 1.361(7) . ? C26 C25 1.536(10) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C25 C28 1.531(12) . ? C25 C27 1.545(11) . ? C33 C36 1.546(9) . ? C33 C34 1.551(10) . ? C33 C35 1.555(9) . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 C32 1.503(10) . ? C29 C30 1.533(12) . ? C29 C31 1.583(9) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? O1 C19 1.388(7) . ? O2 C20 1.191(7) . ? O3 C22 1.186(7) . ? O4 C22 1.379(7) . ? O4 C21 1.465(8) . ? C19 C23 1.526(8) . ? C19 C20 1.533(8) . ? C19 C22 1.542(9) . ? C20 C21 1.518(10) . ? C21 C24 1.338(11) . ? C21 H21A 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 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 C25 P1 C29 114.2(4) . . ? C25 P1 C33 113.9(4) . . ? C29 P1 C33 113.8(4) . . ? C25 P1 H1P 109.4(19) . . ? C29 P1 H1P 105(2) . . ? C33 P1 H1P 98.8(19) . . ? F10 C10 C11 121.0(6) . . ? F10 C10 C9 121.2(7) . . ? C11 C10 C9 117.7(6) . . ? F11 C11 C12 120.3(6) . . ? F11 C11 C10 119.6(6) . . ? C12 C11 C10 120.0(6) . . ? F12 C12 C11 114.8(5) . . ? F12 C12 C7 120.0(5) . . ? C11 C12 C7 125.2(6) . . ? C12 C7 C8 111.4(5) . . ? C12 C7 B1 127.5(5) . . ? C8 C7 B1 120.9(5) . . ? O1 B1 C7 108.8(5) . . ? O1 B1 C1 104.7(4) . . ? C7 B1 C1 113.8(4) . . ? O1 B1 C13 114.0(5) . . ? C7 B1 C13 114.5(5) . . ? C1 B1 C13 100.6(4) . . ? F16 C16 C17 124.4(14) . . ? F16 C16 C15 118.0(14) . . ? C17 C16 C15 117.7(10) . . ? C16 C17 C18 121.0(11) . . ? C16 C17 F17 118.4(9) . . ? C18 C17 F17 120.6(11) . . ? C17 C18 F18 117.4(9) . . ? C17 C18 C13 124.6(9) . . ? F18 C18 C13 118.0(6) . . ? C14 C13 C18 113.0(7) . . ? C14 C13 B1 126.2(7) . . ? C18 C13 B1 120.1(6) . . ? C13 C14 F14 120.9(7) . . ? C13 C14 C15 122.9(9) . . ? F14 C14 C15 116.2(9) . . ? C16 C15 F15 122.3(11) . . ? C16 C15 C14 120.7(11) . . ? F15 C15 C14 116.9(11) . . ? C8 C9 F9 120.9(6) . . ? C8 C9 C10 120.2(6) . . ? F9 C9 C10 118.9(6) . . ? C9 C8 F8 115.8(5) . . ? C9 C8 C7 125.4(6) . . ? F8 C8 C7 118.8(5) . . ? C2 C1 C6 111.8(5) . . ? C2 C1 B1 120.4(5) . . ? C6 C1 B1 127.3(5) . . ? F2 C2 C3 115.2(5) . . ? F2 C2 C1 119.3(5) . . ? C3 C2 C1 125.4(5) . . ? F3 C3 C2 121.0(5) . . ? F3 C3 C4 120.2(5) . . ? C2 C3 C4 118.8(5) . . ? F4 C4 C5 121.3(5) . . ? F4 C4 C3 119.5(6) . . ? C5 C4 C3 119.1(5) . . ? C4 C5 F5 119.3(5) . . ? C4 C5 C6 120.1(5) . . ? F5 C5 C6 120.6(5) . . ? F6 C6 C5 115.3(5) . . ? F6 C6 C1 120.0(5) . . ? C5 C6 C1 124.6(5) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C25 C26 113.5(7) . . ? C28 C25 C27 105.6(7) . . ? C26 C25 C27 109.2(8) . . ? C28 C25 P1 109.4(7) . . ? C26 C25 P1 111.5(5) . . ? C27 C25 P1 107.3(5) . . ? C36 C33 C34 111.3(6) . . ? C36 C33 C35 110.6(6) . . ? C34 C33 C35 107.1(6) . . ? C36 C33 P1 111.0(5) . . ? C34 C33 P1 109.9(5) . . ? C35 C33 P1 106.8(5) . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C33 C36 H36A 109.5 . . ? C33 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C33 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C32 C29 C30 107.8(8) . . ? C32 C29 C31 109.5(7) . . ? C30 C29 C31 108.0(7) . . ? C32 C29 P1 110.3(6) . . ? C30 C29 P1 111.0(6) . . ? C31 C29 P1 110.1(5) . . ? C29 C32 H32A 109.5 . . ? C29 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C29 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C19 O1 B1 126.6(4) . . ? C22 O4 C21 109.6(5) . . ? O1 C19 C23 108.3(5) . . ? O1 C19 C20 120.3(5) . . ? C23 C19 C20 106.8(5) . . ? O1 C19 C22 113.5(5) . . ? C23 C19 C22 105.6(5) . . ? C20 C19 C22 101.2(5) . . ? O2 C20 C21 125.5(6) . . ? O2 C20 C19 128.8(7) . . ? C21 C20 C19 105.6(6) . . ? O3 C22 O4 119.3(6) . . ? O3 C22 C19 129.3(6) . . ? O4 C22 C19 111.3(5) . . ? C24 C21 O4 111.1(8) . . ? C24 C21 C20 122.3(9) . . ? O4 C21 C20 105.9(6) . . ? C24 C21 H21A 105.4 . . ? O4 C21 H21A 105.4 . . ? C20 C21 H21A 105.4 . . ? C19 C23 H23A 109.5 . . ? C19 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C19 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.62 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.424 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.061