# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_erk6325 _database_code_depnum_ccdc_archive 'CCDC 912772' #TrackingRef 'Revision_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H5 F10 P' _chemical_formula_weight 406.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 10.0879(2) _cell_length_b 14.1955(5) _cell_length_c 11.6037(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.101(2) _cell_angle_gamma 90.00 _cell_volume 1528.44(7) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2623 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.765 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 2.672 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6170 _exptl_absorpt_correction_T_max 0.8780 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ? _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15206 _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.77 _diffrn_reflns_theta_max 66.99 _reflns_number_total 2642 _reflns_number_gt 2233 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0678P)^2^+1.2764P] 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 2642 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0595 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1425 _refine_ls_wR_factor_gt 0.1334 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 0.78061(9) 0.22545(6) 0.84555(7) 0.0561(3) Uani 1 1 d . . . C1 C 0.8403(4) 0.1070(2) 0.8271(3) 0.0596(8) Uani 1 1 d . . . C2 C 0.9775(4) 0.0844(3) 0.8627(4) 0.0746(10) Uani 1 1 d . . . H2A H 1.0033 0.0267 0.8376 0.090 Uiso 1 1 calc R . . H2B H 1.0494 0.1259 0.9131 0.090 Uiso 1 1 calc R . . C3 C 0.7209(4) 0.0437(3) 0.7468(4) 0.0834(11) Uani 1 1 d . . . H3A H 0.6913 0.0617 0.6596 0.125 Uiso 1 1 calc R . . H3B H 0.6396 0.0494 0.7712 0.125 Uiso 1 1 calc R . . H3C H 0.7544 -0.0210 0.7575 0.125 Uiso 1 1 calc R . . C11 C 0.9408(3) 0.2798(2) 0.9652(3) 0.0528(7) Uani 1 1 d . . . C12 C 0.9961(4) 0.3621(2) 0.9373(3) 0.0596(8) Uani 1 1 d . . . F12 F 0.9294(3) 0.40293(14) 0.8246(2) 0.0798(6) Uani 1 1 d . . . C13 C 1.1177(4) 0.4058(2) 1.0221(4) 0.0714(10) Uani 1 1 d . . . F13 F 1.1673(3) 0.48427(15) 0.9894(3) 0.1038(9) Uani 1 1 d . . . C14 C 1.1846(4) 0.3677(3) 1.1388(4) 0.0784(11) Uani 1 1 d . . . F14 F 1.3031(3) 0.4087(2) 1.2216(3) 0.1220(11) Uani 1 1 d . . . C15 C 1.1322(4) 0.2883(3) 1.1710(3) 0.0717(10) Uani 1 1 d . . . F15 F 1.1985(2) 0.2509(2) 1.2863(2) 0.1030(8) Uani 1 1 d . . . C16 C 1.0135(3) 0.2452(2) 1.0851(3) 0.0594(8) Uani 1 1 d . . . F16 F 0.9688(2) 0.16596(16) 1.12141(18) 0.0784(6) Uani 1 1 d . . . C21 C 0.6678(3) 0.2101(2) 0.9367(3) 0.0531(7) Uani 1 1 d . . . C22 C 0.6535(3) 0.1313(2) 1.0016(3) 0.0539(7) Uani 1 1 d . . . F22 F 0.73265(18) 0.05368(12) 1.01104(18) 0.0648(5) Uani 1 1 d . . . C23 C 0.5569(3) 0.1272(2) 1.0599(3) 0.0560(7) Uani 1 1 d . . . F23 F 0.5469(2) 0.05019(14) 1.12106(19) 0.0734(5) Uani 1 1 d . . . C24 C 0.4727(3) 0.2040(2) 1.0551(3) 0.0591(8) Uani 1 1 d . . . F24 F 0.3791(2) 0.20163(17) 1.1111(2) 0.0847(6) Uani 1 1 d . . . C25 C 0.4862(3) 0.2839(2) 0.9946(3) 0.0595(8) Uani 1 1 d . . . F25 F 0.4060(2) 0.35987(15) 0.9918(2) 0.0815(6) Uani 1 1 d . . . C26 C 0.5819(3) 0.2858(2) 0.9374(3) 0.0575(8) Uani 1 1 d . . . F26 F 0.5907(2) 0.36617(13) 0.87852(19) 0.0741(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0534(5) 0.0601(5) 0.0456(4) 0.0042(3) 0.0096(3) 0.0064(3) C1 0.0627(19) 0.0607(19) 0.0523(17) -0.0002(14) 0.0192(15) 0.0039(15) C2 0.075(2) 0.069(2) 0.083(2) -0.0006(18) 0.035(2) 0.0130(18) C3 0.089(3) 0.077(2) 0.073(2) -0.0130(19) 0.020(2) -0.001(2) C11 0.0480(16) 0.0581(17) 0.0517(16) -0.0035(13) 0.0190(13) 0.0026(13) C12 0.0666(19) 0.0565(18) 0.064(2) -0.0023(15) 0.0344(16) 0.0094(15) F12 0.1133(17) 0.0612(11) 0.0780(13) 0.0090(10) 0.0518(12) 0.0071(11) C13 0.068(2) 0.0528(18) 0.111(3) -0.0194(19) 0.054(2) -0.0074(16) F13 0.1056(18) 0.0574(12) 0.177(3) -0.0219(14) 0.0862(19) -0.0176(12) C14 0.0476(18) 0.083(3) 0.096(3) -0.037(2) 0.0188(19) -0.0058(18) F14 0.0678(14) 0.125(2) 0.148(2) -0.0650(19) 0.0158(15) -0.0235(14) C15 0.0461(18) 0.098(3) 0.061(2) -0.0076(19) 0.0107(16) 0.0092(18) F15 0.0660(13) 0.146(2) 0.0656(14) -0.0029(14) -0.0077(11) 0.0088(14) C16 0.0457(16) 0.070(2) 0.0596(19) 0.0044(15) 0.0171(15) 0.0030(14) F16 0.0589(11) 0.0993(16) 0.0626(12) 0.0290(11) 0.0085(9) -0.0033(10) C21 0.0391(14) 0.0553(17) 0.0507(16) -0.0001(13) 0.0025(12) 0.0047(12) C22 0.0419(15) 0.0543(17) 0.0544(17) -0.0038(13) 0.0068(13) 0.0085(13) F22 0.0569(10) 0.0566(10) 0.0786(12) 0.0098(9) 0.0240(9) 0.0135(8) C23 0.0473(16) 0.0586(18) 0.0538(17) 0.0010(14) 0.0108(14) -0.0005(13) F23 0.0706(12) 0.0715(12) 0.0771(13) 0.0080(10) 0.0280(10) -0.0002(10) C24 0.0415(15) 0.074(2) 0.0568(18) -0.0076(15) 0.0137(14) 0.0023(14) F24 0.0675(12) 0.1008(16) 0.0964(15) -0.0033(12) 0.0437(12) 0.0094(11) C25 0.0421(15) 0.065(2) 0.0602(18) -0.0111(15) 0.0084(14) 0.0081(14) F25 0.0671(12) 0.0730(13) 0.0959(15) -0.0077(11) 0.0228(11) 0.0245(10) C26 0.0499(17) 0.0520(17) 0.0557(17) -0.0031(14) 0.0045(14) 0.0019(13) F26 0.0749(12) 0.0566(11) 0.0814(13) 0.0084(9) 0.0205(10) 0.0092(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C1 1.826(3) . ? P1 C11 1.837(3) . ? P1 C21 1.846(3) . ? C1 C2 1.320(5) . ? C1 C3 1.499(5) . ? C2 H2A 0.9400 . ? C2 H2B 0.9400 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 H3C 0.9700 . ? C11 C16 1.383(4) . ? C11 C12 1.387(5) . ? C12 F12 1.345(4) . ? C12 C13 1.382(5) . ? C13 F13 1.336(4) . ? C13 C14 1.366(6) . ? C14 F14 1.338(4) . ? C14 C15 1.358(6) . ? C15 F15 1.349(4) . ? C15 C16 1.366(5) . ? C16 F16 1.340(4) . ? C21 C26 1.382(4) . ? C21 C22 1.387(4) . ? C22 F22 1.340(3) . ? C22 C23 1.389(5) . ? C23 F23 1.328(4) . ? C23 C24 1.369(4) . ? C24 F24 1.340(4) . ? C24 C25 1.369(5) . ? C25 F25 1.341(4) . ? C25 C26 1.370(5) . ? C26 F26 1.351(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 P1 C11 104.03(14) . . ? C1 P1 C21 105.32(14) . . ? C11 P1 C21 100.00(13) . . ? C2 C1 C3 122.5(3) . . ? C2 C1 P1 122.8(3) . . ? C3 C1 P1 113.8(3) . . ? C1 C2 H2A 120.0 . . ? C1 C2 H2B 120.0 . . ? H2A C2 H2B 120.0 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C16 C11 C12 115.6(3) . . ? C16 C11 P1 124.9(2) . . ? C12 C11 P1 119.5(2) . . ? F12 C12 C13 117.7(3) . . ? F12 C12 C11 119.8(3) . . ? C13 C12 C11 122.5(3) . . ? F13 C13 C14 121.2(4) . . ? F13 C13 C12 119.9(4) . . ? C14 C13 C12 118.9(3) . . ? F14 C14 C15 119.9(4) . . ? F14 C14 C13 119.6(4) . . ? C15 C14 C13 120.5(3) . . ? F15 C15 C14 120.3(3) . . ? F15 C15 C16 119.9(4) . . ? C14 C15 C16 119.8(3) . . ? F16 C16 C15 117.0(3) . . ? F16 C16 C11 120.3(3) . . ? C15 C16 C11 122.8(3) . . ? C26 C21 C22 115.2(3) . . ? C26 C21 P1 116.1(2) . . ? C22 C21 P1 128.7(2) . . ? F22 C22 C21 121.5(3) . . ? F22 C22 C23 115.8(3) . . ? C21 C22 C23 122.7(3) . . ? F23 C23 C24 120.1(3) . . ? F23 C23 C22 120.6(3) . . ? C24 C23 C22 119.3(3) . . ? F24 C24 C25 120.0(3) . . ? F24 C24 C23 120.3(3) . . ? C25 C24 C23 119.7(3) . . ? F25 C25 C24 119.9(3) . . ? F25 C25 C26 120.4(3) . . ? C24 C25 C26 119.7(3) . . ? F26 C26 C25 117.4(3) . . ? F26 C26 C21 119.2(3) . . ? C25 C26 C21 123.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 P1 C1 C2 -19.5(3) . . . . ? C21 P1 C1 C2 -124.2(3) . . . . ? C11 P1 C1 C3 171.6(3) . . . . ? C21 P1 C1 C3 66.9(3) . . . . ? C1 P1 C11 C16 -58.3(3) . . . . ? C21 P1 C11 C16 50.4(3) . . . . ? C1 P1 C11 C12 122.0(2) . . . . ? C21 P1 C11 C12 -129.3(2) . . . . ? C16 C11 C12 F12 -177.5(3) . . . . ? P1 C11 C12 F12 2.2(4) . . . . ? C16 C11 C12 C13 1.4(4) . . . . ? P1 C11 C12 C13 -178.9(2) . . . . ? F12 C12 C13 F13 -2.0(4) . . . . ? C11 C12 C13 F13 179.1(3) . . . . ? F12 C12 C13 C14 177.6(3) . . . . ? C11 C12 C13 C14 -1.3(5) . . . . ? F13 C13 C14 F14 -1.0(5) . . . . ? C12 C13 C14 F14 179.4(3) . . . . ? F13 C13 C14 C15 179.5(3) . . . . ? C12 C13 C14 C15 -0.1(5) . . . . ? F14 C14 C15 F15 0.4(5) . . . . ? C13 C14 C15 F15 180.0(3) . . . . ? F14 C14 C15 C16 -178.2(3) . . . . ? C13 C14 C15 C16 1.4(5) . . . . ? F15 C15 C16 F16 -0.1(5) . . . . ? C14 C15 C16 F16 178.6(3) . . . . ? F15 C15 C16 C11 -179.9(3) . . . . ? C14 C15 C16 C11 -1.2(5) . . . . ? C12 C11 C16 F16 -179.9(3) . . . . ? P1 C11 C16 F16 0.4(4) . . . . ? C12 C11 C16 C15 -0.2(5) . . . . ? P1 C11 C16 C15 -179.9(3) . . . . ? C1 P1 C21 C26 -164.9(2) . . . . ? C11 P1 C21 C26 87.4(2) . . . . ? C1 P1 C21 C22 12.6(3) . . . . ? C11 P1 C21 C22 -95.1(3) . . . . ? C26 C21 C22 F22 -178.4(3) . . . . ? P1 C21 C22 F22 4.0(4) . . . . ? C26 C21 C22 C23 2.0(4) . . . . ? P1 C21 C22 C23 -175.6(2) . . . . ? F22 C22 C23 F23 0.4(4) . . . . ? C21 C22 C23 F23 -180.0(3) . . . . ? F22 C22 C23 C24 179.6(3) . . . . ? C21 C22 C23 C24 -0.8(5) . . . . ? F23 C23 C24 F24 -0.6(4) . . . . ? C22 C23 C24 F24 -179.8(3) . . . . ? F23 C23 C24 C25 178.4(3) . . . . ? C22 C23 C24 C25 -0.8(5) . . . . ? F24 C24 C25 F25 0.2(5) . . . . ? C23 C24 C25 F25 -178.7(3) . . . . ? F24 C24 C25 C26 -179.9(3) . . . . ? C23 C24 C25 C26 1.2(5) . . . . ? F25 C25 C26 F26 -0.4(4) . . . . ? C24 C25 C26 F26 179.7(3) . . . . ? F25 C25 C26 C21 180.0(3) . . . . ? C24 C25 C26 C21 0.1(5) . . . . ? C22 C21 C26 F26 178.8(3) . . . . ? P1 C21 C26 F26 -3.3(4) . . . . ? C22 C21 C26 C25 -1.6(4) . . . . ? P1 C21 C26 C25 176.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 66.99 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.687 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.049 data_erk6472 _database_code_depnum_ccdc_archive 'CCDC 912773' #TrackingRef 'Revision_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H11 B F20 N P' _chemical_formula_weight 831.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 9.4074(2) _cell_length_b 15.6502(6) _cell_length_c 22.7817(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.343(2) _cell_angle_gamma 90.00 _cell_volume 3333.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 5285 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1640 _exptl_absorpt_coefficient_mu 2.032 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5536 _exptl_absorpt_correction_T_max 0.8543 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ? _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19676 _diffrn_reflns_av_R_equivalents 0.041 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 4.82 _diffrn_reflns_theta_max 67.02 _reflns_number_total 5697 _reflns_number_gt 4614 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. One distorted half molecule of dichloromethane, which could not be refined satisfactorily, was removed using the program SQUEEZE (A.L. Spek, University of Utrecht, Netherlands). ; loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 0.500 132 38 ' ' 2 0.000 0.500 0.000 132 38 ' ' _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^)+(0.0498P)^2^+1.2844P] 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 5697 _refine_ls_number_parameters 497 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1130 _refine_ls_wR_factor_gt 0.1063 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.31441(6) 0.95239(4) 0.35091(3) 0.04598(16) Uani 1 1 d . . . B1 B 0.5788(3) 0.74027(16) 0.40447(11) 0.0419(5) Uani 1 1 d . . . N1 N 0.70593(19) 0.74199(11) 0.45971(8) 0.0447(4) Uani 1 1 d . . . C1 C 0.3671(2) 0.83815(14) 0.35290(10) 0.0473(5) Uani 1 1 d . . . H1 H 0.4118 0.8239 0.3168 0.057 Uiso 1 1 calc R . . C2 C 0.4774(2) 0.82470(14) 0.40781(10) 0.0457(5) Uani 1 1 d . . . H2A H 0.4259 0.8200 0.4428 0.055 Uiso 1 1 calc R . . H2B H 0.5388 0.8753 0.4129 0.055 Uiso 1 1 calc R . . C3 C 0.2309(3) 0.78482(17) 0.35474(13) 0.0645(7) Uani 1 1 d . . . H3A H 0.2546 0.7246 0.3537 0.097 Uiso 1 1 calc R . . H3B H 0.1630 0.7989 0.3209 0.097 Uiso 1 1 calc R . . H3C H 0.1889 0.7973 0.3908 0.097 Uiso 1 1 calc R . . C11 C 0.2206(2) 0.97193(15) 0.27607(10) 0.0480(5) Uani 1 1 d . . . C12 C 0.2031(3) 0.91814(16) 0.22735(11) 0.0556(6) Uani 1 1 d . . . C13 C 0.1196(3) 0.9401(2) 0.17616(12) 0.0690(8) Uani 1 1 d . . . C14 C 0.0524(3) 1.0175(2) 0.17160(13) 0.0741(9) Uani 1 1 d . . . C15 C 0.0680(3) 1.07358(18) 0.21765(13) 0.0656(7) Uani 1 1 d . . . C16 C 0.1499(2) 1.04982(16) 0.26876(11) 0.0536(6) Uani 1 1 d . . . C21 C 0.4856(2) 1.00634(13) 0.34159(10) 0.0468(5) Uani 1 1 d . . . C22 C 0.5614(2) 0.99957(14) 0.29311(11) 0.0493(5) Uani 1 1 d . . . C23 C 0.6833(3) 1.04524(17) 0.28747(13) 0.0634(7) Uani 1 1 d . . . C24 C 0.7344(3) 1.10073(19) 0.33143(17) 0.0794(9) Uani 1 1 d . . . C25 C 0.6644(3) 1.10915(19) 0.38031(17) 0.0815(9) Uani 1 1 d . . . C26 C 0.5429(3) 1.06176(16) 0.38514(13) 0.0641(7) Uani 1 1 d . . . C31 C 0.5045(2) 0.64606(13) 0.41333(9) 0.0428(5) Uani 1 1 d . . . C32 C 0.3963(2) 0.63319(15) 0.44934(10) 0.0487(5) Uani 1 1 d . . . C33 C 0.3355(2) 0.55478(16) 0.45871(11) 0.0548(6) Uani 1 1 d . . . C34 C 0.3836(3) 0.48323(16) 0.43271(11) 0.0581(6) Uani 1 1 d . . . C35 C 0.4942(3) 0.49063(14) 0.39851(11) 0.0553(6) Uani 1 1 d . . . C36 C 0.5509(2) 0.57055(14) 0.38995(10) 0.0486(5) Uani 1 1 d . . . C41 C 0.6552(2) 0.75438(13) 0.34360(9) 0.0429(5) Uani 1 1 d . . . C42 C 0.5983(2) 0.72448(14) 0.28842(10) 0.0473(5) Uani 1 1 d . . . C43 C 0.6463(3) 0.74807(16) 0.23579(10) 0.0553(6) Uani 1 1 d . . . C44 C 0.7590(3) 0.80350(17) 0.23606(11) 0.0599(6) Uani 1 1 d . . . C45 C 0.8176(2) 0.83658(16) 0.28847(11) 0.0536(6) Uani 1 1 d . . . C46 C 0.7656(2) 0.81250(15) 0.34005(10) 0.0485(5) Uani 1 1 d . . . C52 C 0.8257(3) 0.69675(17) 0.45746(12) 0.0582(6) Uani 1 1 d . . . H52 H 0.8351 0.6632 0.4239 0.070 Uiso 1 1 calc R . . C53 C 0.9354(3) 0.6977(2) 0.50255(14) 0.0731(8) Uani 1 1 d . . . H53 H 1.0188 0.6657 0.4995 0.088 Uiso 1 1 calc R . . C54 C 0.9226(3) 0.74566(19) 0.55206(14) 0.0764(8) Uani 1 1 d . . . H54 H 0.9970 0.7478 0.5831 0.092 Uiso 1 1 calc R . . C55 C 0.7998(3) 0.78983(19) 0.55499(13) 0.0755(8) Uani 1 1 d . . . H55 H 0.7878 0.8225 0.5887 0.091 Uiso 1 1 calc R . . C56 C 0.6926(3) 0.78706(16) 0.50876(11) 0.0589(6) Uani 1 1 d . . . H56 H 0.6077 0.8177 0.5117 0.071 Uiso 1 1 calc R . . F12 F 0.26799(18) 0.84171(10) 0.22774(7) 0.0723(4) Uani 1 1 d . . . F13 F 0.1084(2) 0.88578(14) 0.13022(8) 0.1013(6) Uani 1 1 d . . . F14 F -0.0258(2) 1.03976(16) 0.12060(8) 0.1112(7) Uani 1 1 d . . . F15 F 0.00643(18) 1.15042(11) 0.21259(9) 0.0933(6) Uani 1 1 d . . . F16 F 0.16183(15) 1.10686(9) 0.31339(7) 0.0661(4) Uani 1 1 d . . . F22 F 0.51542(14) 0.94690(10) 0.24848(6) 0.0622(4) Uani 1 1 d . . . F23 F 0.75014(16) 1.03779(12) 0.23861(8) 0.0856(5) Uani 1 1 d . . . F24 F 0.8531(2) 1.14659(13) 0.32567(12) 0.1189(8) Uani 1 1 d . . . F25 F 0.7132(2) 1.16419(15) 0.42320(12) 0.1339(9) Uani 1 1 d . . . F26 F 0.47834(19) 1.07146(12) 0.43456(8) 0.0923(6) Uani 1 1 d . . . F32 F 0.34535(16) 0.69892(9) 0.47903(6) 0.0664(4) Uani 1 1 d . . . F33 F 0.23060(16) 0.54803(11) 0.49408(7) 0.0771(5) Uani 1 1 d . . . F34 F 0.32723(19) 0.40653(10) 0.44187(7) 0.0831(5) Uani 1 1 d . . . F35 F 0.5473(2) 0.42112(9) 0.37485(7) 0.0783(5) Uani 1 1 d . . . F36 F 0.66223(16) 0.57162(8) 0.35690(7) 0.0637(4) Uani 1 1 d . . . F42 F 0.48373(15) 0.67181(9) 0.28420(6) 0.0593(3) Uani 1 1 d . . . F43 F 0.58251(19) 0.71742(10) 0.18427(6) 0.0768(4) Uani 1 1 d . . . F44 F 0.8070(2) 0.82715(12) 0.18483(7) 0.0853(5) Uani 1 1 d . . . F45 F 0.92592(15) 0.89351(11) 0.28990(7) 0.0745(4) Uani 1 1 d . . . F46 F 0.82649(15) 0.85206(9) 0.38949(6) 0.0633(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0409(3) 0.0496(3) 0.0470(3) 0.0008(2) 0.0024(2) 0.0059(2) B1 0.0396(12) 0.0462(13) 0.0396(13) 0.0004(10) 0.0025(10) 0.0008(10) N1 0.0442(10) 0.0458(9) 0.0434(10) 0.0047(8) 0.0026(8) 0.0002(8) C1 0.0414(11) 0.0486(12) 0.0508(13) 0.0034(10) 0.0002(9) 0.0016(9) C2 0.0446(12) 0.0467(11) 0.0454(12) 0.0018(10) 0.0029(9) 0.0017(9) C3 0.0468(13) 0.0621(15) 0.0810(18) 0.0156(13) -0.0085(12) -0.0086(11) C11 0.0351(11) 0.0558(13) 0.0523(13) 0.0072(11) 0.0013(9) -0.0064(10) C12 0.0505(13) 0.0599(14) 0.0550(14) 0.0035(11) -0.0004(11) -0.0124(11) C13 0.0601(16) 0.093(2) 0.0504(15) 0.0025(14) -0.0078(12) -0.0300(15) C14 0.0494(15) 0.104(2) 0.0642(18) 0.0325(17) -0.0138(13) -0.0190(15) C15 0.0411(13) 0.0740(17) 0.0790(19) 0.0300(15) -0.0047(12) -0.0026(12) C16 0.0377(12) 0.0604(14) 0.0617(15) 0.0112(12) 0.0012(10) -0.0050(10) C21 0.0448(12) 0.0412(11) 0.0522(13) -0.0020(9) -0.0043(10) 0.0064(9) C22 0.0421(12) 0.0483(12) 0.0556(14) 0.0009(10) -0.0030(10) 0.0018(10) C23 0.0438(13) 0.0635(15) 0.0825(19) 0.0157(14) 0.0055(13) 0.0012(12) C24 0.0496(15) 0.0624(17) 0.123(3) 0.0019(17) -0.0068(17) -0.0135(13) C25 0.0623(17) 0.0624(17) 0.114(3) -0.0289(17) -0.0158(18) -0.0067(14) C26 0.0595(15) 0.0576(14) 0.0726(18) -0.0171(13) -0.0048(13) 0.0070(12) C31 0.0395(11) 0.0475(12) 0.0409(11) 0.0031(9) 0.0029(9) 0.0011(9) C32 0.0465(12) 0.0556(13) 0.0446(12) 0.0077(10) 0.0075(10) 0.0043(10) C33 0.0454(13) 0.0680(16) 0.0511(14) 0.0181(12) 0.0053(10) -0.0076(11) C34 0.0661(15) 0.0540(14) 0.0519(14) 0.0165(11) -0.0045(12) -0.0176(12) C35 0.0743(16) 0.0412(12) 0.0495(14) 0.0048(10) 0.0025(12) -0.0006(11) C36 0.0497(13) 0.0491(12) 0.0481(13) 0.0053(10) 0.0107(10) 0.0012(10) C41 0.0398(11) 0.0449(11) 0.0442(12) -0.0014(9) 0.0049(9) -0.0004(9) C42 0.0481(12) 0.0457(11) 0.0490(13) -0.0013(10) 0.0099(10) -0.0014(10) C43 0.0664(15) 0.0580(14) 0.0420(13) -0.0055(11) 0.0090(11) 0.0026(12) C44 0.0628(15) 0.0666(15) 0.0544(15) 0.0108(12) 0.0253(12) 0.0071(13) C45 0.0432(12) 0.0594(14) 0.0600(15) 0.0118(11) 0.0136(11) -0.0043(10) C46 0.0429(12) 0.0520(12) 0.0503(13) 0.0025(10) 0.0038(10) -0.0015(10) C52 0.0486(13) 0.0640(15) 0.0610(15) 0.0045(12) 0.0013(11) 0.0111(11) C53 0.0519(15) 0.0827(19) 0.081(2) 0.0179(16) -0.0069(13) 0.0111(14) C54 0.078(2) 0.0753(18) 0.0681(19) 0.0153(15) -0.0252(15) -0.0105(16) C55 0.090(2) 0.0742(18) 0.0564(16) -0.0051(13) -0.0196(15) 0.0074(16) C56 0.0673(16) 0.0597(14) 0.0484(14) -0.0052(11) 0.0004(12) 0.0081(12) F12 0.0883(11) 0.0664(9) 0.0602(9) -0.0129(7) -0.0012(8) -0.0053(8) F13 0.1138(14) 0.1244(15) 0.0602(10) -0.0115(10) -0.0150(10) -0.0394(12) F14 0.0819(12) 0.1628(19) 0.0789(12) 0.0473(12) -0.0354(10) -0.0214(12) F15 0.0658(10) 0.0900(12) 0.1197(15) 0.0471(11) -0.0091(9) 0.0121(9) F16 0.0619(9) 0.0569(8) 0.0781(10) 0.0030(7) 0.0019(7) 0.0105(7) F22 0.0532(8) 0.0809(9) 0.0525(8) -0.0084(7) 0.0060(6) -0.0050(7) F23 0.0560(9) 0.1052(13) 0.0981(13) 0.0264(10) 0.0202(9) -0.0044(8) F24 0.0662(11) 0.0989(14) 0.189(2) -0.0015(14) 0.0042(13) -0.0369(10) F25 0.1069(15) 0.1145(16) 0.173(2) -0.0782(16) -0.0157(15) -0.0295(13) F26 0.0843(11) 0.1076(13) 0.0837(12) -0.0492(10) 0.0039(9) 0.0012(10) F32 0.0715(9) 0.0673(9) 0.0660(9) 0.0055(7) 0.0321(7) 0.0095(7) F33 0.0613(9) 0.0963(11) 0.0774(10) 0.0260(9) 0.0238(8) -0.0116(8) F34 0.1070(13) 0.0637(9) 0.0770(11) 0.0210(8) 0.0036(9) -0.0323(9) F35 0.1205(14) 0.0449(8) 0.0710(10) 0.0020(7) 0.0170(9) 0.0029(8) F36 0.0705(9) 0.0500(7) 0.0758(10) 0.0020(7) 0.0315(8) 0.0086(6) F42 0.0641(8) 0.0602(8) 0.0527(8) -0.0080(6) 0.0032(6) -0.0183(7) F43 0.1005(12) 0.0860(11) 0.0442(8) -0.0110(7) 0.0094(8) -0.0058(9) F44 0.0968(12) 0.1053(13) 0.0604(10) 0.0150(9) 0.0383(9) -0.0046(10) F45 0.0532(8) 0.0844(10) 0.0875(11) 0.0225(8) 0.0147(7) -0.0177(7) F46 0.0597(8) 0.0718(9) 0.0563(8) 0.0023(7) -0.0028(6) -0.0234(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C21 1.851(2) . ? P1 C1 1.855(2) . ? P1 C11 1.857(2) . ? B1 C2 1.636(3) . ? B1 N1 1.638(3) . ? B1 C41 1.646(3) . ? B1 C31 1.654(3) . ? N1 C52 1.336(3) . ? N1 C56 1.339(3) . ? C1 C3 1.534(3) . ? C1 C2 1.549(3) . ? C1 H1 0.9900 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 H3C 0.9700 . ? C11 C12 1.388(3) . ? C11 C16 1.390(3) . ? C12 F12 1.343(3) . ? C12 C13 1.376(4) . ? C13 F13 1.343(3) . ? C13 C14 1.365(4) . ? C14 F14 1.350(3) . ? C14 C15 1.363(4) . ? C15 F15 1.334(3) . ? C15 C16 1.375(3) . ? C16 F16 1.348(3) . ? C21 C26 1.382(3) . ? C21 C22 1.384(3) . ? C22 F22 1.343(3) . ? C22 C23 1.369(3) . ? C23 F23 1.343(3) . ? C23 C24 1.372(4) . ? C24 F24 1.346(3) . ? C24 C25 1.362(5) . ? C25 F25 1.345(3) . ? C25 C26 1.377(4) . ? C26 F26 1.346(3) . ? C31 C36 1.386(3) . ? C31 C32 1.391(3) . ? C32 F32 1.348(3) . ? C32 C33 1.380(3) . ? C33 F33 1.346(3) . ? C33 C34 1.367(4) . ? C34 F34 1.338(3) . ? C34 C35 1.372(4) . ? C35 F35 1.335(3) . ? C35 C36 1.382(3) . ? C36 F36 1.356(3) . ? C41 C46 1.390(3) . ? C41 C42 1.392(3) . ? C42 F42 1.352(2) . ? C42 C43 1.378(3) . ? C43 F43 1.346(3) . ? C43 C44 1.369(4) . ? C44 F44 1.349(3) . ? C44 C45 1.361(4) . ? C45 F45 1.351(3) . ? C45 C46 1.375(3) . ? C46 F46 1.355(3) . ? C52 C53 1.374(4) . ? C52 H52 0.9400 . ? C53 C54 1.371(4) . ? C53 H53 0.9400 . ? C54 C55 1.354(4) . ? C54 H54 0.9400 . ? C55 C56 1.376(4) . ? C55 H55 0.9400 . ? C56 H56 0.9400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C21 P1 C1 102.05(10) . . ? C21 P1 C11 98.67(10) . . ? C1 P1 C11 106.25(11) . . ? C2 B1 N1 109.32(17) . . ? C2 B1 C41 104.00(17) . . ? N1 B1 C41 107.19(17) . . ? C2 B1 C31 117.27(18) . . ? N1 B1 C31 101.73(16) . . ? C41 B1 C31 116.88(18) . . ? C52 N1 C56 117.9(2) . . ? C52 N1 B1 120.59(19) . . ? C56 N1 B1 121.49(19) . . ? C3 C1 C2 113.03(19) . . ? C3 C1 P1 107.64(16) . . ? C2 C1 P1 107.72(15) . . ? C3 C1 H1 109.5 . . ? C2 C1 H1 109.5 . . ? P1 C1 H1 109.5 . . ? C1 C2 B1 114.46(18) . . ? C1 C2 H2A 108.6 . . ? B1 C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? B1 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C12 C11 C16 115.0(2) . . ? C12 C11 P1 129.55(18) . . ? C16 C11 P1 115.28(18) . . ? F12 C12 C13 116.4(2) . . ? F12 C12 C11 121.4(2) . . ? C13 C12 C11 122.2(3) . . ? F13 C13 C14 120.4(3) . . ? F13 C13 C12 119.4(3) . . ? C14 C13 C12 120.1(3) . . ? F14 C14 C15 119.9(3) . . ? F14 C14 C13 119.9(3) . . ? C15 C14 C13 120.2(2) . . ? F15 C15 C14 120.3(3) . . ? F15 C15 C16 121.0(3) . . ? C14 C15 C16 118.7(3) . . ? F16 C16 C15 116.9(2) . . ? F16 C16 C11 119.5(2) . . ? C15 C16 C11 123.7(3) . . ? C26 C21 C22 115.2(2) . . ? C26 C21 P1 118.7(2) . . ? C22 C21 P1 126.04(17) . . ? F22 C22 C23 116.9(2) . . ? F22 C22 C21 120.0(2) . . ? C23 C22 C21 123.1(2) . . ? F23 C23 C22 120.4(3) . . ? F23 C23 C24 120.1(2) . . ? C22 C23 C24 119.5(3) . . ? F24 C24 C25 120.6(3) . . ? F24 C24 C23 119.6(3) . . ? C25 C24 C23 119.7(3) . . ? F25 C25 C24 119.9(3) . . ? F25 C25 C26 120.5(3) . . ? C24 C25 C26 119.6(3) . . ? F26 C26 C25 117.5(2) . . ? F26 C26 C21 119.7(2) . . ? C25 C26 C21 122.9(3) . . ? C36 C31 C32 112.7(2) . . ? C36 C31 B1 123.92(19) . . ? C32 C31 B1 123.22(19) . . ? F32 C32 C33 115.1(2) . . ? F32 C32 C31 120.6(2) . . ? C33 C32 C31 124.2(2) . . ? F33 C33 C34 119.7(2) . . ? F33 C33 C32 120.4(2) . . ? C34 C33 C32 119.9(2) . . ? F34 C34 C33 120.8(2) . . ? F34 C34 C35 120.2(2) . . ? C33 C34 C35 119.0(2) . . ? F35 C35 C34 120.1(2) . . ? F35 C35 C36 120.8(2) . . ? C34 C35 C36 119.0(2) . . ? F36 C36 C35 115.1(2) . . ? F36 C36 C31 119.87(19) . . ? C35 C36 C31 125.0(2) . . ? C46 C41 C42 112.5(2) . . ? C46 C41 B1 122.38(19) . . ? C42 C41 B1 123.76(19) . . ? F42 C42 C43 115.9(2) . . ? F42 C42 C41 119.57(19) . . ? C43 C42 C41 124.4(2) . . ? F43 C43 C44 120.0(2) . . ? F43 C43 C42 120.4(2) . . ? C44 C43 C42 119.6(2) . . ? F44 C44 C45 120.8(2) . . ? F44 C44 C43 120.2(2) . . ? C45 C44 C43 118.9(2) . . ? F45 C45 C44 120.2(2) . . ? F45 C45 C46 119.9(2) . . ? C44 C45 C46 119.8(2) . . ? F46 C46 C45 115.3(2) . . ? F46 C46 C41 120.04(19) . . ? C45 C46 C41 124.6(2) . . ? N1 C52 C53 122.2(3) . . ? N1 C52 H52 118.9 . . ? C53 C52 H52 118.9 . . ? C54 C53 C52 119.6(3) . . ? C54 C53 H53 120.2 . . ? C52 C53 H53 120.2 . . ? C55 C54 C53 118.2(3) . . ? C55 C54 H54 120.9 . . ? C53 C54 H54 120.9 . . ? C54 C55 C56 120.2(3) . . ? C54 C55 H55 119.9 . . ? C56 C55 H55 119.9 . . ? N1 C56 C55 121.8(3) . . ? N1 C56 H56 119.1 . . ? C55 C56 H56 119.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 B1 N1 C52 -159.2(2) . . . . ? C41 B1 N1 C52 -47.1(3) . . . . ? C31 B1 N1 C52 76.1(2) . . . . ? C2 B1 N1 C56 22.1(3) . . . . ? C41 B1 N1 C56 134.2(2) . . . . ? C31 B1 N1 C56 -102.6(2) . . . . ? C21 P1 C1 C3 -174.79(17) . . . . ? C11 P1 C1 C3 -71.91(19) . . . . ? C21 P1 C1 C2 63.03(17) . . . . ? C11 P1 C1 C2 165.91(15) . . . . ? C3 C1 C2 B1 82.7(3) . . . . ? P1 C1 C2 B1 -158.56(16) . . . . ? N1 B1 C2 C1 171.06(17) . . . . ? C41 B1 C2 C1 56.8(2) . . . . ? C31 B1 C2 C1 -73.9(2) . . . . ? C21 P1 C11 C12 98.8(2) . . . . ? C1 P1 C11 C12 -6.5(2) . . . . ? C21 P1 C11 C16 -85.66(17) . . . . ? C1 P1 C11 C16 169.00(16) . . . . ? C16 C11 C12 F12 178.4(2) . . . . ? P1 C11 C12 F12 -6.1(3) . . . . ? C16 C11 C12 C13 -1.1(3) . . . . ? P1 C11 C12 C13 174.38(19) . . . . ? F12 C12 C13 F13 -0.5(4) . . . . ? C11 C12 C13 F13 179.1(2) . . . . ? F12 C12 C13 C14 -178.5(2) . . . . ? C11 C12 C13 C14 1.1(4) . . . . ? F13 C13 C14 F14 0.0(4) . . . . ? C12 C13 C14 F14 178.0(2) . . . . ? F13 C13 C14 C15 -177.8(2) . . . . ? C12 C13 C14 C15 0.2(4) . . . . ? F14 C14 C15 F15 0.0(4) . . . . ? C13 C14 C15 F15 177.7(2) . . . . ? F14 C14 C15 C16 -179.0(2) . . . . ? C13 C14 C15 C16 -1.3(4) . . . . ? F15 C15 C16 F16 1.4(3) . . . . ? C14 C15 C16 F16 -179.5(2) . . . . ? F15 C15 C16 C11 -177.8(2) . . . . ? C14 C15 C16 C11 1.2(4) . . . . ? C12 C11 C16 F16 -179.2(2) . . . . ? P1 C11 C16 F16 4.6(3) . . . . ? C12 C11 C16 C15 0.0(3) . . . . ? P1 C11 C16 C15 -176.18(19) . . . . ? C1 P1 C21 C26 -118.18(19) . . . . ? C11 P1 C21 C26 133.03(19) . . . . ? C1 P1 C21 C22 64.7(2) . . . . ? C11 P1 C21 C22 -44.0(2) . . . . ? C26 C21 C22 F22 179.5(2) . . . . ? P1 C21 C22 F22 -3.4(3) . . . . ? C26 C21 C22 C23 -1.2(3) . . . . ? P1 C21 C22 C23 176.00(18) . . . . ? F22 C22 C23 F23 1.3(3) . . . . ? C21 C22 C23 F23 -178.1(2) . . . . ? F22 C22 C23 C24 179.3(2) . . . . ? C21 C22 C23 C24 -0.1(4) . . . . ? F23 C23 C24 F24 -1.0(4) . . . . ? C22 C23 C24 F24 -179.1(2) . . . . ? F23 C23 C24 C25 178.7(3) . . . . ? C22 C23 C24 C25 0.6(4) . . . . ? F24 C24 C25 F25 0.5(5) . . . . ? C23 C24 C25 F25 -179.2(3) . . . . ? F24 C24 C25 C26 179.8(3) . . . . ? C23 C24 C25 C26 0.1(5) . . . . ? F25 C25 C26 F26 -1.5(4) . . . . ? C24 C25 C26 F26 179.2(3) . . . . ? F25 C25 C26 C21 177.9(3) . . . . ? C24 C25 C26 C21 -1.4(5) . . . . ? C22 C21 C26 F26 -178.7(2) . . . . ? P1 C21 C26 F26 3.9(3) . . . . ? C22 C21 C26 C25 1.9(4) . . . . ? P1 C21 C26 C25 -175.5(2) . . . . ? C2 B1 C31 C36 153.6(2) . . . . ? N1 B1 C31 C36 -87.3(2) . . . . ? C41 B1 C31 C36 29.1(3) . . . . ? C2 B1 C31 C32 -32.1(3) . . . . ? N1 B1 C31 C32 87.0(2) . . . . ? C41 B1 C31 C32 -156.6(2) . . . . ? C36 C31 C32 F32 175.37(19) . . . . ? B1 C31 C32 F32 0.5(3) . . . . ? C36 C31 C32 C33 -3.2(3) . . . . ? B1 C31 C32 C33 -178.1(2) . . . . ? F32 C32 C33 F33 1.7(3) . . . . ? C31 C32 C33 F33 -179.7(2) . . . . ? F32 C32 C33 C34 -177.2(2) . . . . ? C31 C32 C33 C34 1.4(4) . . . . ? F33 C33 C34 F34 0.2(4) . . . . ? C32 C33 C34 F34 179.2(2) . . . . ? F33 C33 C34 C35 -177.6(2) . . . . ? C32 C33 C34 C35 1.3(4) . . . . ? F34 C34 C35 F35 -0.9(4) . . . . ? C33 C34 C35 F35 177.0(2) . . . . ? F34 C34 C35 C36 -179.7(2) . . . . ? C33 C34 C35 C36 -1.8(4) . . . . ? F35 C35 C36 F36 -0.5(3) . . . . ? C34 C35 C36 F36 178.3(2) . . . . ? F35 C35 C36 C31 -179.0(2) . . . . ? C34 C35 C36 C31 -0.2(4) . . . . ? C32 C31 C36 F36 -175.86(19) . . . . ? B1 C31 C36 F36 -1.0(3) . . . . ? C32 C31 C36 C35 2.6(3) . . . . ? B1 C31 C36 C35 177.5(2) . . . . ? C2 B1 C41 C46 75.0(2) . . . . ? N1 B1 C41 C46 -40.7(3) . . . . ? C31 B1 C41 C46 -154.0(2) . . . . ? C2 B1 C41 C42 -90.8(2) . . . . ? N1 B1 C41 C42 153.49(19) . . . . ? C31 B1 C41 C42 40.2(3) . . . . ? C46 C41 C42 F42 -175.63(19) . . . . ? B1 C41 C42 F42 -8.6(3) . . . . ? C46 C41 C42 C43 1.0(3) . . . . ? B1 C41 C42 C43 168.0(2) . . . . ? F42 C42 C43 F43 -1.7(3) . . . . ? C41 C42 C43 F43 -178.4(2) . . . . ? F42 C42 C43 C44 177.9(2) . . . . ? C41 C42 C43 C44 1.1(4) . . . . ? F43 C43 C44 F44 -0.4(4) . . . . ? C42 C43 C44 F44 -180.0(2) . . . . ? F43 C43 C44 C45 177.1(2) . . . . ? C42 C43 C44 C45 -2.4(4) . . . . ? F44 C44 C45 F45 -0.4(4) . . . . ? C43 C44 C45 F45 -177.9(2) . . . . ? F44 C44 C45 C46 179.1(2) . . . . ? C43 C44 C45 C46 1.5(4) . . . . ? F45 C45 C46 F46 2.5(3) . . . . ? C44 C45 C46 F46 -177.0(2) . . . . ? F45 C45 C46 C41 -179.8(2) . . . . ? C44 C45 C46 C41 0.8(4) . . . . ? C42 C41 C46 F46 175.66(19) . . . . ? B1 C41 C46 F46 8.4(3) . . . . ? C42 C41 C46 C45 -2.0(3) . . . . ? B1 C41 C46 C45 -169.2(2) . . . . ? C56 N1 C52 C53 -2.3(4) . . . . ? B1 N1 C52 C53 179.0(2) . . . . ? N1 C52 C53 C54 0.7(4) . . . . ? C52 C53 C54 C55 0.9(4) . . . . ? C53 C54 C55 C56 -1.0(5) . . . . ? C52 N1 C56 C55 2.2(4) . . . . ? B1 N1 C56 C55 -179.0(2) . . . . ? C54 C55 C56 N1 -0.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 67.02 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.187 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.041 data_erk6349 _database_code_depnum_ccdc_archive 'CCDC 912774' #TrackingRef 'Revision_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H9 B F20 N P' _chemical_formula_weight 793.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 '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 10.7188(3) _cell_length_b 12.7599(6) _cell_length_c 13.1819(5) _cell_angle_alpha 78.178(4) _cell_angle_beta 78.512(3) _cell_angle_gamma 80.597(3) _cell_volume 1715.13(11) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 5461 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.215 _exptl_crystal_description column _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.536 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 1.944 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5333 _exptl_absorpt_correction_T_max 0.6857 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ? _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24911 _diffrn_reflns_av_R_equivalents 0.043 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.24 _diffrn_reflns_theta_max 66.76 _reflns_number_total 5920 _reflns_number_gt 5299 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. An disordered pentane molecule was found in the asymmetrical unit and could not be satisfactorily refined. The program SQUEEZE (A. L. Spek J. Appl. Cryst.,2003, 36, 7-13) was therefore used to remove mathematically the effect of the solvent. ; loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.000 0.742 275 66 ' ' _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^)+(0.0619P)^2^+0.5971P] 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 5920 _refine_ls_number_parameters 471 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1116 _refine_ls_wR_factor_gt 0.1085 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.12300(4) 0.66440(3) 0.77317(3) 0.03954(13) Uani 1 1 d . . . B1 B 0.1092(2) 0.32896(16) 0.82242(16) 0.0407(4) Uani 1 1 d . . . C1 C 0.09177(18) 0.54019(14) 0.73538(14) 0.0416(4) Uani 1 1 d . . . H1 H 0.1578 0.5207 0.6758 0.050 Uiso 1 1 calc R . . C2 C 0.10165(18) 0.45330(14) 0.83506(14) 0.0423(4) Uani 1 1 d . . . H2A H 0.0270 0.4691 0.8887 0.051 Uiso 1 1 calc R . . H2B H 0.1782 0.4606 0.8619 0.051 Uiso 1 1 calc R . . C3 C -0.0417(2) 0.56162(17) 0.70448(17) 0.0546(5) Uani 1 1 d . . . H3A H -0.0570 0.4999 0.6784 0.082 Uiso 1 1 calc R . . H3B H -0.0463 0.6253 0.6499 0.082 Uiso 1 1 calc R . . H3C H -0.1061 0.5732 0.7655 0.082 Uiso 1 1 calc R . . N1 N -0.03056(15) 0.30966(12) 0.81122(12) 0.0431(3) Uani 1 1 d . . . C4 C -0.13274(19) 0.29533(15) 0.81328(14) 0.0441(4) Uani 1 1 d . . . C5 C -0.2628(2) 0.2781(2) 0.81541(19) 0.0615(6) Uani 1 1 d . . . H5A H -0.3187 0.3066 0.8737 0.092 Uiso 1 1 calc R . . H5B H -0.2672 0.2014 0.8241 0.092 Uiso 1 1 calc R . . H5C H -0.2902 0.3147 0.7499 0.092 Uiso 1 1 calc R . . C11 C 0.14292(18) 0.76950(14) 0.65320(14) 0.0415(4) Uani 1 1 d . . . C12 C 0.1403(2) 0.87304(16) 0.67135(15) 0.0513(5) Uani 1 1 d . . . F12 F 0.13161(16) 0.88848(10) 0.77055(9) 0.0721(4) Uani 1 1 d . . . C13 C 0.1472(3) 0.96212(16) 0.59278(18) 0.0620(6) Uani 1 1 d . . . F13 F 0.1439(2) 1.06024(10) 0.61524(12) 0.0968(6) Uani 1 1 d . . . C14 C 0.1553(2) 0.94968(17) 0.49074(17) 0.0597(5) Uani 1 1 d . . . F14 F 0.16115(17) 1.03567(11) 0.41287(11) 0.0861(5) Uani 1 1 d . . . C15 C 0.1572(2) 0.84880(17) 0.46866(15) 0.0535(5) Uani 1 1 d . . . F15 F 0.16414(15) 0.83697(11) 0.36892(9) 0.0729(4) Uani 1 1 d . . . C16 C 0.15232(19) 0.76069(15) 0.54857(14) 0.0458(4) Uani 1 1 d . . . F16 F 0.15736(13) 0.66504(9) 0.52032(9) 0.0601(3) Uani 1 1 d . . . C21 C 0.29378(18) 0.63080(14) 0.78835(14) 0.0424(4) Uani 1 1 d . . . C22 C 0.3282(2) 0.64406(18) 0.88052(16) 0.0535(5) Uani 1 1 d . . . F22 F 0.23933(13) 0.68312(13) 0.95522(10) 0.0750(4) Uani 1 1 d . . . C23 C 0.4516(2) 0.6181(2) 0.90012(18) 0.0634(6) Uani 1 1 d . . . F23 F 0.48077(15) 0.63037(16) 0.99132(12) 0.0929(5) Uani 1 1 d . . . C24 C 0.5459(2) 0.5757(2) 0.82743(19) 0.0630(6) Uani 1 1 d . . . F24 F 0.66566(13) 0.54717(15) 0.84766(14) 0.0916(5) Uani 1 1 d . . . C25 C 0.5168(2) 0.56209(18) 0.73465(18) 0.0575(5) Uani 1 1 d . . . F25 F 0.60914(13) 0.52152(13) 0.66339(12) 0.0809(4) Uani 1 1 d . . . C26 C 0.39225(19) 0.58904(15) 0.71672(15) 0.0469(4) Uani 1 1 d . . . F26 F 0.36947(12) 0.57347(11) 0.62508(9) 0.0621(3) Uani 1 1 d . . . C31 C 0.13621(17) 0.23810(14) 0.92659(14) 0.0414(4) Uani 1 1 d . . . C32 C 0.16052(19) 0.25787(15) 1.01992(15) 0.0467(4) Uani 1 1 d . . . F32 F 0.16869(14) 0.35811(9) 1.03247(9) 0.0623(3) Uani 1 1 d . . . C33 C 0.1776(2) 0.17775(18) 1.10596(15) 0.0567(5) Uani 1 1 d . . . F33 F 0.19872(17) 0.20247(12) 1.19466(10) 0.0826(5) Uani 1 1 d . . . C34 C 0.1714(2) 0.07300(18) 1.10074(16) 0.0603(6) Uani 1 1 d . . . F34 F 0.18609(18) -0.00565(12) 1.18387(11) 0.0877(5) Uani 1 1 d . . . C35 C 0.1497(2) 0.04815(16) 1.00988(17) 0.0549(5) Uani 1 1 d . . . F35 F 0.14504(15) -0.05519(9) 1.00374(11) 0.0732(4) Uani 1 1 d . . . C36 C 0.13273(19) 0.13035(15) 0.92591(14) 0.0460(4) Uani 1 1 d . . . F36 F 0.10927(13) 0.10127(9) 0.83932(9) 0.0603(3) Uani 1 1 d . . . C41 C 0.21201(17) 0.30359(13) 0.71847(13) 0.0394(4) Uani 1 1 d . . . C42 C 0.34169(19) 0.29634(16) 0.71993(15) 0.0489(4) Uani 1 1 d . . . F42 F 0.38114(12) 0.30931(13) 0.80778(10) 0.0700(4) Uani 1 1 d . . . C43 C 0.4375(2) 0.27791(19) 0.63651(17) 0.0569(5) Uani 1 1 d . . . F43 F 0.56182(12) 0.27082(15) 0.64416(12) 0.0871(5) Uani 1 1 d . . . C44 C 0.4047(2) 0.26558(17) 0.54428(15) 0.0537(5) Uani 1 1 d . . . F44 F 0.49687(14) 0.24548(12) 0.46270(10) 0.0760(4) Uani 1 1 d . . . C45 C 0.2786(2) 0.27319(16) 0.53737(14) 0.0501(5) Uani 1 1 d . . . F45 F 0.24558(14) 0.26164(13) 0.44745(9) 0.0735(4) Uani 1 1 d . . . C46 C 0.18528(18) 0.29207(14) 0.62266(14) 0.0437(4) Uani 1 1 d . . . F46 F 0.06292(11) 0.29974(11) 0.60857(9) 0.0620(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0466(3) 0.0356(2) 0.0348(2) -0.00433(17) -0.00593(18) -0.00439(18) B1 0.0453(11) 0.0397(10) 0.0376(10) -0.0032(8) -0.0107(8) -0.0076(8) C1 0.0475(10) 0.0357(9) 0.0409(9) -0.0039(7) -0.0097(7) -0.0046(7) C2 0.0502(10) 0.0389(9) 0.0380(9) -0.0036(7) -0.0099(7) -0.0073(8) C3 0.0563(12) 0.0484(11) 0.0602(12) -0.0005(9) -0.0204(10) -0.0091(9) N1 0.0490(10) 0.0406(8) 0.0395(8) -0.0050(6) -0.0081(7) -0.0073(7) C4 0.0510(12) 0.0422(10) 0.0408(10) -0.0112(8) -0.0087(8) -0.0050(8) C5 0.0511(12) 0.0710(14) 0.0719(14) -0.0286(12) -0.0151(10) -0.0099(10) C11 0.0479(10) 0.0368(9) 0.0381(9) -0.0035(7) -0.0072(7) -0.0049(7) C12 0.0703(13) 0.0436(10) 0.0403(10) -0.0076(8) -0.0091(9) -0.0084(9) F12 0.1274(12) 0.0466(6) 0.0471(7) -0.0135(5) -0.0142(7) -0.0190(7) C13 0.0896(16) 0.0357(10) 0.0590(13) -0.0041(9) -0.0109(11) -0.0107(10) F13 0.1767(18) 0.0385(7) 0.0757(10) -0.0052(6) -0.0184(10) -0.0253(8) C14 0.0755(14) 0.0477(11) 0.0485(12) 0.0071(9) -0.0083(10) -0.0086(10) F14 0.1298(13) 0.0549(8) 0.0599(8) 0.0198(6) -0.0122(8) -0.0155(8) C15 0.0639(12) 0.0555(12) 0.0354(10) -0.0014(8) -0.0052(8) -0.0034(9) F15 0.1039(11) 0.0748(9) 0.0356(6) -0.0022(6) -0.0112(6) -0.0091(7) C16 0.0548(11) 0.0426(10) 0.0393(9) -0.0078(8) -0.0072(8) -0.0048(8) F16 0.0924(9) 0.0473(6) 0.0430(6) -0.0128(5) -0.0140(6) -0.0071(6) C21 0.0489(10) 0.0377(9) 0.0389(9) -0.0009(7) -0.0074(8) -0.0083(7) C22 0.0538(11) 0.0619(12) 0.0448(10) -0.0085(9) -0.0102(9) -0.0064(9) F22 0.0689(8) 0.1129(11) 0.0483(7) -0.0335(7) -0.0139(6) 0.0027(7) C23 0.0643(14) 0.0776(15) 0.0521(12) -0.0061(11) -0.0210(10) -0.0140(11) F23 0.0793(10) 0.1419(15) 0.0685(9) -0.0268(9) -0.0350(8) -0.0088(9) C24 0.0470(11) 0.0725(14) 0.0680(14) -0.0003(11) -0.0161(10) -0.0111(10) F24 0.0498(8) 0.1243(13) 0.1009(12) -0.0118(10) -0.0244(7) -0.0083(8) C25 0.0491(11) 0.0563(12) 0.0600(13) -0.0053(10) 0.0030(9) -0.0080(9) F25 0.0540(7) 0.0973(11) 0.0833(10) -0.0243(8) 0.0077(7) 0.0004(7) C26 0.0519(11) 0.0443(10) 0.0425(10) -0.0039(8) -0.0044(8) -0.0104(8) F26 0.0600(7) 0.0782(8) 0.0501(7) -0.0242(6) -0.0001(5) -0.0099(6) C31 0.0451(10) 0.0392(9) 0.0378(9) -0.0038(7) -0.0056(7) -0.0051(7) C32 0.0557(11) 0.0426(10) 0.0408(10) -0.0056(8) -0.0099(8) -0.0033(8) F32 0.0974(9) 0.0473(6) 0.0484(6) -0.0098(5) -0.0269(6) -0.0080(6) C33 0.0715(14) 0.0584(12) 0.0366(10) -0.0052(9) -0.0137(9) 0.0030(10) F33 0.1299(13) 0.0745(9) 0.0448(7) -0.0097(6) -0.0365(8) 0.0084(8) C34 0.0740(14) 0.0511(12) 0.0435(11) 0.0094(9) -0.0077(10) 0.0023(10) F34 0.1354(14) 0.0611(8) 0.0519(8) 0.0175(6) -0.0225(8) 0.0031(8) C35 0.0645(13) 0.0391(10) 0.0552(12) 0.0009(9) -0.0057(10) -0.0070(9) F35 0.1017(10) 0.0375(6) 0.0762(9) 0.0031(6) -0.0161(7) -0.0129(6) C36 0.0547(11) 0.0421(10) 0.0407(10) -0.0051(8) -0.0083(8) -0.0078(8) F36 0.0913(9) 0.0424(6) 0.0526(7) -0.0094(5) -0.0193(6) -0.0143(6) C41 0.0480(10) 0.0317(8) 0.0385(9) -0.0017(7) -0.0107(7) -0.0072(7) C42 0.0521(11) 0.0546(11) 0.0431(10) -0.0096(8) -0.0114(8) -0.0111(9) F42 0.0559(7) 0.1068(11) 0.0578(7) -0.0286(7) -0.0166(6) -0.0149(7) C43 0.0465(11) 0.0669(13) 0.0571(12) -0.0113(10) -0.0040(9) -0.0125(9) F43 0.0447(7) 0.1382(14) 0.0844(10) -0.0356(10) -0.0043(6) -0.0176(8) C44 0.0564(12) 0.0560(12) 0.0431(10) -0.0055(9) 0.0041(9) -0.0104(9) F44 0.0740(9) 0.0907(10) 0.0547(7) -0.0160(7) 0.0153(6) -0.0139(7) C45 0.0673(13) 0.0484(10) 0.0340(9) -0.0037(8) -0.0099(8) -0.0086(9) F45 0.0887(10) 0.0949(10) 0.0385(6) -0.0167(6) -0.0149(6) -0.0053(8) C46 0.0506(11) 0.0405(9) 0.0397(9) -0.0024(7) -0.0122(8) -0.0055(8) F46 0.0540(7) 0.0882(9) 0.0486(6) -0.0171(6) -0.0195(5) -0.0034(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C21 1.8518(19) . ? P1 C11 1.8534(17) . ? P1 C1 1.8535(18) . ? B1 N1 1.597(3) . ? B1 C2 1.616(3) . ? B1 C41 1.631(3) . ? B1 C31 1.646(3) . ? C1 C3 1.531(3) . ? C1 C2 1.545(2) . ? C1 H1 0.9900 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 H3C 0.9700 . ? N1 C4 1.134(2) . ? C4 C5 1.441(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C5 H5C 0.9700 . ? C11 C12 1.385(3) . ? C11 C16 1.389(3) . ? C12 F12 1.345(2) . ? C12 C13 1.373(3) . ? C13 F13 1.338(2) . ? C13 C14 1.371(3) . ? C14 F14 1.340(2) . ? C14 C15 1.373(3) . ? C15 F15 1.340(2) . ? C15 C16 1.374(3) . ? C16 F16 1.337(2) . ? C21 C26 1.384(3) . ? C21 C22 1.387(3) . ? C22 F22 1.341(2) . ? C22 C23 1.373(3) . ? C23 F23 1.346(3) . ? C23 C24 1.371(3) . ? C24 F24 1.340(3) . ? C24 C25 1.371(3) . ? C25 F25 1.339(3) . ? C25 C26 1.378(3) . ? C26 F26 1.338(2) . ? C31 C36 1.383(3) . ? C31 C32 1.386(3) . ? C32 F32 1.342(2) . ? C32 C33 1.382(3) . ? C33 F33 1.341(2) . ? C33 C34 1.365(3) . ? C34 F34 1.341(2) . ? C34 C35 1.371(3) . ? C35 F35 1.347(2) . ? C35 C36 1.379(3) . ? C36 F36 1.350(2) . ? C41 C42 1.382(3) . ? C41 C46 1.390(2) . ? C42 F42 1.358(2) . ? C42 C43 1.377(3) . ? C43 F43 1.343(2) . ? C43 C44 1.376(3) . ? C44 F44 1.344(2) . ? C44 C45 1.359(3) . ? C45 F45 1.344(2) . ? C45 C46 1.381(3) . ? C46 F46 1.346(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C21 P1 C11 98.18(8) . . ? C21 P1 C1 101.76(8) . . ? C11 P1 C1 108.27(8) . . ? N1 B1 C2 107.64(15) . . ? N1 B1 C41 109.71(14) . . ? C2 B1 C41 110.87(15) . . ? N1 B1 C31 101.65(14) . . ? C2 B1 C31 115.60(15) . . ? C41 B1 C31 110.83(15) . . ? C3 C1 C2 113.48(15) . . ? C3 C1 P1 108.00(13) . . ? C2 C1 P1 103.92(12) . . ? C3 C1 H1 110.4 . . ? C2 C1 H1 110.4 . . ? P1 C1 H1 110.4 . . ? C1 C2 B1 117.04(15) . . ? C1 C2 H2A 108.0 . . ? B1 C2 H2A 108.0 . . ? C1 C2 H2B 108.0 . . ? B1 C2 H2B 108.0 . . ? H2A C2 H2B 107.3 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C4 N1 B1 173.52(17) . . ? N1 C4 C5 179.5(2) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C12 C11 C16 115.40(16) . . ? C12 C11 P1 114.99(13) . . ? C16 C11 P1 129.49(14) . . ? F12 C12 C13 117.45(18) . . ? F12 C12 C11 119.12(16) . . ? C13 C12 C11 123.43(18) . . ? F13 C13 C14 120.17(19) . . ? F13 C13 C12 120.7(2) . . ? C14 C13 C12 119.13(19) . . ? F14 C14 C13 120.1(2) . . ? F14 C14 C15 120.2(2) . . ? C13 C14 C15 119.70(18) . . ? F15 C15 C14 119.59(18) . . ? F15 C15 C16 120.40(19) . . ? C14 C15 C16 120.01(18) . . ? F16 C16 C15 116.34(17) . . ? F16 C16 C11 121.35(16) . . ? C15 C16 C11 122.31(18) . . ? C26 C21 C22 115.63(18) . . ? C26 C21 P1 125.75(14) . . ? C22 C21 P1 118.57(14) . . ? F22 C22 C23 117.21(18) . . ? F22 C22 C21 120.12(18) . . ? C23 C22 C21 122.7(2) . . ? F23 C23 C24 119.4(2) . . ? F23 C23 C22 120.9(2) . . ? C24 C23 C22 119.7(2) . . ? F24 C24 C25 120.4(2) . . ? F24 C24 C23 119.9(2) . . ? C25 C24 C23 119.8(2) . . ? F25 C25 C24 119.7(2) . . ? F25 C25 C26 120.9(2) . . ? C24 C25 C26 119.4(2) . . ? F26 C26 C25 116.76(18) . . ? F26 C26 C21 120.44(17) . . ? C25 C26 C21 122.80(19) . . ? C36 C31 C32 114.14(16) . . ? C36 C31 B1 119.39(16) . . ? C32 C31 B1 126.46(16) . . ? F32 C32 C33 115.28(17) . . ? F32 C32 C31 121.36(16) . . ? C33 C32 C31 123.36(18) . . ? F33 C33 C34 119.92(18) . . ? F33 C33 C32 120.4(2) . . ? C34 C33 C32 119.65(19) . . ? F34 C34 C33 120.5(2) . . ? F34 C34 C35 119.8(2) . . ? C33 C34 C35 119.70(18) . . ? F35 C35 C34 120.02(18) . . ? F35 C35 C36 121.05(19) . . ? C34 C35 C36 118.93(19) . . ? F36 C36 C35 116.27(17) . . ? F36 C36 C31 119.50(16) . . ? C35 C36 C31 124.21(18) . . ? C42 C41 C46 113.49(17) . . ? C42 C41 B1 119.05(16) . . ? C46 C41 B1 127.40(16) . . ? F42 C42 C43 115.84(18) . . ? F42 C42 C41 119.61(17) . . ? C43 C42 C41 124.55(18) . . ? F43 C43 C44 119.75(19) . . ? F43 C43 C42 121.17(19) . . ? C44 C43 C42 119.08(19) . . ? F44 C44 C45 120.81(19) . . ? F44 C44 C43 119.96(19) . . ? C45 C44 C43 119.22(18) . . ? F45 C45 C44 119.62(18) . . ? F45 C45 C46 120.43(19) . . ? C44 C45 C46 119.95(18) . . ? F46 C46 C45 116.01(16) . . ? F46 C46 C41 120.28(16) . . ? C45 C46 C41 123.70(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C21 P1 C1 C3 -172.04(13) . . . . ? C11 P1 C1 C3 -69.22(14) . . . . ? C21 P1 C1 C2 67.15(13) . . . . ? C11 P1 C1 C2 169.97(12) . . . . ? C3 C1 C2 B1 75.6(2) . . . . ? P1 C1 C2 B1 -167.40(13) . . . . ? N1 B1 C2 C1 -73.91(19) . . . . ? C41 B1 C2 C1 46.1(2) . . . . ? C31 B1 C2 C1 173.29(15) . . . . ? C2 B1 N1 C4 -78.5(16) . . . . ? C41 B1 N1 C4 160.8(15) . . . . ? C31 B1 N1 C4 43.4(16) . . . . ? B1 N1 C4 C5 110(26) . . . . ? C21 P1 C11 C12 -87.50(16) . . . . ? C1 P1 C11 C12 167.17(15) . . . . ? C21 P1 C11 C16 96.83(19) . . . . ? C1 P1 C11 C16 -8.5(2) . . . . ? C16 C11 C12 F12 -179.84(18) . . . . ? P1 C11 C12 F12 3.9(3) . . . . ? C16 C11 C12 C13 -0.4(3) . . . . ? P1 C11 C12 C13 -176.73(19) . . . . ? F12 C12 C13 F13 -0.7(4) . . . . ? C11 C12 C13 F13 179.8(2) . . . . ? F12 C12 C13 C14 -179.6(2) . . . . ? C11 C12 C13 C14 1.0(4) . . . . ? F13 C13 C14 F14 0.6(4) . . . . ? C12 C13 C14 F14 179.5(2) . . . . ? F13 C13 C14 C15 -179.3(2) . . . . ? C12 C13 C14 C15 -0.4(4) . . . . ? F14 C14 C15 F15 -0.4(3) . . . . ? C13 C14 C15 F15 179.5(2) . . . . ? F14 C14 C15 C16 179.5(2) . . . . ? C13 C14 C15 C16 -0.7(4) . . . . ? F15 C15 C16 F16 1.2(3) . . . . ? C14 C15 C16 F16 -178.61(19) . . . . ? F15 C15 C16 C11 -178.89(18) . . . . ? C14 C15 C16 C11 1.3(3) . . . . ? C12 C11 C16 F16 179.16(18) . . . . ? P1 C11 C16 F16 -5.2(3) . . . . ? C12 C11 C16 C15 -0.7(3) . . . . ? P1 C11 C16 C15 174.96(16) . . . . ? C11 P1 C21 C26 -61.90(17) . . . . ? C1 P1 C21 C26 48.80(17) . . . . ? C11 P1 C21 C22 120.66(16) . . . . ? C1 P1 C21 C22 -128.64(16) . . . . ? C26 C21 C22 F22 -179.42(18) . . . . ? P1 C21 C22 F22 -1.7(3) . . . . ? C26 C21 C22 C23 0.2(3) . . . . ? P1 C21 C22 C23 177.90(18) . . . . ? F22 C22 C23 F23 0.8(3) . . . . ? C21 C22 C23 F23 -178.9(2) . . . . ? F22 C22 C23 C24 178.6(2) . . . . ? C21 C22 C23 C24 -1.0(4) . . . . ? F23 C23 C24 F24 -0.1(4) . . . . ? C22 C23 C24 F24 -178.0(2) . . . . ? F23 C23 C24 C25 179.5(2) . . . . ? C22 C23 C24 C25 1.6(4) . . . . ? F24 C24 C25 F25 -0.9(3) . . . . ? C23 C24 C25 F25 179.4(2) . . . . ? F24 C24 C25 C26 178.2(2) . . . . ? C23 C24 C25 C26 -1.5(3) . . . . ? F25 C25 C26 F26 -0.5(3) . . . . ? C24 C25 C26 F26 -179.62(18) . . . . ? F25 C25 C26 C21 179.76(18) . . . . ? C24 C25 C26 C21 0.7(3) . . . . ? C22 C21 C26 F26 -179.73(17) . . . . ? P1 C21 C26 F26 2.8(3) . . . . ? C22 C21 C26 C25 0.0(3) . . . . ? P1 C21 C26 C25 -177.55(15) . . . . ? N1 B1 C31 C36 58.0(2) . . . . ? C2 B1 C31 C36 174.25(17) . . . . ? C41 B1 C31 C36 -58.5(2) . . . . ? N1 B1 C31 C32 -120.50(19) . . . . ? C2 B1 C31 C32 -4.3(3) . . . . ? C41 B1 C31 C32 123.0(2) . . . . ? C36 C31 C32 F32 179.06(17) . . . . ? B1 C31 C32 F32 -2.4(3) . . . . ? C36 C31 C32 C33 -1.1(3) . . . . ? B1 C31 C32 C33 177.43(19) . . . . ? F32 C32 C33 F33 0.9(3) . . . . ? C31 C32 C33 F33 -178.89(19) . . . . ? F32 C32 C33 C34 -179.8(2) . . . . ? C31 C32 C33 C34 0.4(3) . . . . ? F33 C33 C34 F34 0.1(4) . . . . ? C32 C33 C34 F34 -179.2(2) . . . . ? F33 C33 C34 C35 -180.0(2) . . . . ? C32 C33 C34 C35 0.7(3) . . . . ? F34 C34 C35 F35 -0.9(3) . . . . ? C33 C34 C35 F35 179.2(2) . . . . ? F34 C34 C35 C36 178.9(2) . . . . ? C33 C34 C35 C36 -1.0(3) . . . . ? F35 C35 C36 F36 1.1(3) . . . . ? C34 C35 C36 F36 -178.73(19) . . . . ? F35 C35 C36 C31 179.96(18) . . . . ? C34 C35 C36 C31 0.1(3) . . . . ? C32 C31 C36 F36 179.72(17) . . . . ? B1 C31 C36 F36 1.0(3) . . . . ? C32 C31 C36 C35 0.9(3) . . . . ? B1 C31 C36 C35 -177.80(18) . . . . ? N1 B1 C41 C42 -168.48(15) . . . . ? C2 B1 C41 C42 72.8(2) . . . . ? C31 B1 C41 C42 -57.0(2) . . . . ? N1 B1 C41 C46 14.5(2) . . . . ? C2 B1 C41 C46 -104.3(2) . . . . ? C31 B1 C41 C46 125.95(18) . . . . ? C46 C41 C42 F42 178.09(17) . . . . ? B1 C41 C42 F42 0.7(3) . . . . ? C46 C41 C42 C43 -1.0(3) . . . . ? B1 C41 C42 C43 -178.38(19) . . . . ? F42 C42 C43 F43 1.6(3) . . . . ? C41 C42 C43 F43 -179.33(19) . . . . ? F42 C42 C43 C44 -179.04(19) . . . . ? C41 C42 C43 C44 0.0(3) . . . . ? F43 C43 C44 F44 0.6(3) . . . . ? C42 C43 C44 F44 -178.72(19) . . . . ? F43 C43 C44 C45 -179.8(2) . . . . ? C42 C43 C44 C45 0.8(3) . . . . ? F44 C44 C45 F45 -0.7(3) . . . . ? C43 C44 C45 F45 179.76(19) . . . . ? F44 C44 C45 C46 178.91(18) . . . . ? C43 C44 C45 C46 -0.6(3) . . . . ? F45 C45 C46 F46 -1.2(3) . . . . ? C44 C45 C46 F46 179.21(17) . . . . ? F45 C45 C46 C41 179.22(17) . . . . ? C44 C45 C46 C41 -0.4(3) . . . . ? C42 C41 C46 F46 -178.47(16) . . . . ? B1 C41 C46 F46 -1.3(3) . . . . ? C42 C41 C46 C45 1.1(3) . . . . ? B1 C41 C46 C45 178.32(17) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 66.76 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.195 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.049 data_erk6705 _database_code_depnum_ccdc_archive 'CCDC 912775' #TrackingRef 'Revision_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34.50 H21 B F20 N P' _chemical_formula_weight 871.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.4280(7) _cell_length_b 20.0877(8) _cell_length_c 15.7738(4) _cell_angle_alpha 90.00 _cell_angle_beta 124.926(2) _cell_angle_gamma 90.00 _cell_volume 7125.5(4) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4713 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.624 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3480 _exptl_absorpt_coefficient_mu 1.928 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6241 _exptl_absorpt_correction_T_max 0.8306 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17145 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.40 _diffrn_reflns_theta_max 66.95 _reflns_number_total 5948 _reflns_number_gt 4883 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. One half molecule of pentane was found in the asymmetric unit and is disordered across an inversion centre. Several restraints (SADI, SIMU, SAME and ISOR) were used in order to improve refinement stability. ; _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^)+(0.0575P)^2^+8.8407P] 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 5948 _refine_ls_number_parameters 547 _refine_ls_number_restraints 67 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1356 _refine_ls_wR_factor_gt 0.1266 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.080 _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 0.20437(3) 0.06524(4) 0.11395(5) 0.04696(19) Uani 1 1 d . . . B1 B 0.38224(13) 0.13958(15) 0.3044(2) 0.0433(7) Uani 1 1 d . . . C1 C 0.26297(11) 0.12948(13) 0.1834(2) 0.0477(6) Uani 1 1 d . . . H1 H 0.2641 0.1459 0.2437 0.057 Uiso 1 1 calc R . . C2 C 0.32297(11) 0.09713(14) 0.2201(2) 0.0473(6) Uani 1 1 d . . . H2A H 0.3236 0.0892 0.1595 0.057 Uiso 1 1 calc R . . H2B H 0.3252 0.0536 0.2503 0.057 Uiso 1 1 calc R . . C3 C 0.24473(14) 0.18623(16) 0.1051(2) 0.0643(8) Uani 1 1 d . . . H3A H 0.2724 0.2230 0.1386 0.096 Uiso 1 1 calc R . . H3B H 0.2049 0.2012 0.0797 0.096 Uiso 1 1 calc R . . H3C H 0.2453 0.1703 0.0477 0.096 Uiso 1 1 calc R . . C4 C 0.37439(11) 0.15819(13) 0.3961(2) 0.0450(6) Uani 1 1 d . . . N1 N 0.36856(10) 0.16816(12) 0.46079(17) 0.0487(5) Uani 1 1 d . . . C5 C 0.36464(14) 0.19035(16) 0.5459(2) 0.0571(7) Uani 1 1 d . . . C6 C 0.3250(3) 0.2493(3) 0.5075(4) 0.141(2) Uani 1 1 d U . . H6A H 0.2851 0.2360 0.4518 0.211 Uiso 1 1 calc R . . H6B H 0.3397 0.2822 0.4821 0.211 Uiso 1 1 calc R . . H6C H 0.3244 0.2684 0.5634 0.211 Uiso 1 1 calc R . . C7 C 0.42779(19) 0.2091(2) 0.6333(3) 0.0979(13) Uani 1 1 d U . . H7A H 0.4283 0.2252 0.6918 0.147 Uiso 1 1 calc R . . H7B H 0.4421 0.2438 0.6100 0.147 Uiso 1 1 calc R . . H7C H 0.4533 0.1703 0.6540 0.147 Uiso 1 1 calc R . . C8 C 0.3440(3) 0.1331(3) 0.5772(4) 0.1219(18) Uani 1 1 d U . . H8A H 0.3036 0.1217 0.5211 0.183 Uiso 1 1 calc R . . H8B H 0.3452 0.1450 0.6379 0.183 Uiso 1 1 calc R . . H8C H 0.3698 0.0952 0.5930 0.183 Uiso 1 1 calc R . . C11 C 0.22776(12) 0.00074(13) 0.2133(2) 0.0498(6) Uani 1 1 d . . . C12 C 0.23847(13) 0.01052(14) 0.3095(2) 0.0547(7) Uani 1 1 d . . . F12 F 0.23024(9) 0.07180(9) 0.33498(13) 0.0723(5) Uani 1 1 d . . . C13 C 0.25885(15) -0.03856(17) 0.3825(3) 0.0667(8) Uani 1 1 d . . . F13 F 0.26973(12) -0.02536(12) 0.47579(17) 0.1004(7) Uani 1 1 d . . . C14 C 0.26950(15) -0.10080(17) 0.3609(3) 0.0720(9) Uani 1 1 d . . . F14 F 0.29030(12) -0.14890(11) 0.4328(2) 0.1093(8) Uani 1 1 d . . . C15 C 0.25945(15) -0.11363(15) 0.2675(3) 0.0699(9) Uani 1 1 d . . . F15 F 0.27021(11) -0.17425(9) 0.2467(2) 0.1047(8) Uani 1 1 d . . . C16 C 0.23867(13) -0.06314(15) 0.1951(2) 0.0598(8) Uani 1 1 d . . . F16 F 0.22973(11) -0.07807(10) 0.10389(17) 0.0868(6) Uani 1 1 d . . . C21 C 0.13847(11) 0.09889(14) 0.10473(19) 0.0467(6) Uani 1 1 d . . . C22 C 0.08562(13) 0.06651(15) 0.0345(2) 0.0528(7) Uani 1 1 d . . . F22 F 0.08667(8) 0.00984(9) -0.00969(14) 0.0699(5) Uani 1 1 d . . . C23 C 0.03080(13) 0.09001(18) 0.0052(2) 0.0621(8) Uani 1 1 d . . . F23 F -0.01894(8) 0.05704(12) -0.06655(17) 0.0904(7) Uani 1 1 d . . . C24 C 0.02765(14) 0.14733(17) 0.0475(2) 0.0622(8) Uani 1 1 d . . . F24 F -0.02558(9) 0.17070(12) 0.01928(17) 0.0906(6) Uani 1 1 d . . . C25 C 0.07834(15) 0.18032(15) 0.1197(2) 0.0589(8) Uani 1 1 d . . . F25 F 0.07596(10) 0.23556(10) 0.16475(15) 0.0806(6) Uani 1 1 d . . . C26 C 0.13281(13) 0.15609(14) 0.1475(2) 0.0521(7) Uani 1 1 d . . . F26 F 0.18050(8) 0.19152(9) 0.21929(14) 0.0675(5) Uani 1 1 d . . . C31 C 0.39141(11) 0.20795(14) 0.25885(19) 0.0469(6) Uani 1 1 d . . . C32 C 0.38096(12) 0.27217(15) 0.2755(2) 0.0535(7) Uani 1 1 d . . . F32 F 0.35854(9) 0.28301(8) 0.33190(14) 0.0679(5) Uani 1 1 d . . . C33 C 0.39034(14) 0.32853(16) 0.2368(2) 0.0649(8) Uani 1 1 d . . . F33 F 0.37769(10) 0.38924(10) 0.25500(17) 0.0900(6) Uani 1 1 d . . . C34 C 0.41233(16) 0.3211(2) 0.1781(3) 0.0774(11) Uani 1 1 d . . . F34 F 0.42334(12) 0.37579(13) 0.1419(2) 0.1169(9) Uani 1 1 d . . . C35 C 0.42233(16) 0.2591(2) 0.1567(3) 0.0765(10) Uani 1 1 d . . . F35 F 0.44298(12) 0.25157(15) 0.0972(2) 0.1154(9) Uani 1 1 d . . . C36 C 0.41174(14) 0.20419(17) 0.1958(2) 0.0614(8) Uani 1 1 d . . . F36 F 0.42224(10) 0.14385(11) 0.17137(15) 0.0819(6) Uani 1 1 d . . . C41 C 0.44526(11) 0.09748(13) 0.3647(2) 0.0449(6) Uani 1 1 d . . . C42 C 0.49600(12) 0.12402(14) 0.4511(2) 0.0517(6) Uani 1 1 d . . . F42 F 0.49246(7) 0.18416(9) 0.48622(14) 0.0687(5) Uani 1 1 d . . . C43 C 0.55092(13) 0.09388(18) 0.5055(2) 0.0649(8) Uani 1 1 d . . . F43 F 0.59801(8) 0.12316(12) 0.58898(17) 0.0993(7) Uani 1 1 d . . . C44 C 0.55684(13) 0.03329(17) 0.4735(3) 0.0625(8) Uani 1 1 d . . . F44 F 0.60980(9) 0.00148(11) 0.52579(17) 0.0901(6) Uani 1 1 d . . . C45 C 0.50875(15) 0.00423(16) 0.3889(3) 0.0636(8) Uani 1 1 d . . . F45 F 0.51411(10) -0.05624(11) 0.35828(19) 0.0955(7) Uani 1 1 d . . . C46 C 0.45441(13) 0.03632(15) 0.3358(2) 0.0559(7) Uani 1 1 d . . . F46 F 0.40958(9) 0.00402(10) 0.25224(16) 0.0866(6) Uani 1 1 d . . . C101 C 0.6003(5) 0.4482(6) 0.8081(9) 0.078(3) Uani 0.488(15) 1 d PDU A 1 H10A H 0.6368 0.4231 0.8372 0.118 Uiso 0.488(15) 1 calc PR A 1 H10B H 0.6073 0.4852 0.8533 0.118 Uiso 0.488(15) 1 calc PR A 1 H10C H 0.5872 0.4650 0.7405 0.118 Uiso 0.488(15) 1 calc PR A 1 C102 C 0.5515(5) 0.4021(5) 0.7973(8) 0.103(5) Uani 0.488(15) 1 d PDU A 1 H10D H 0.5427 0.3643 0.7513 0.123 Uiso 0.488(15) 1 calc PR A 1 H10E H 0.5624 0.3856 0.8646 0.123 Uiso 0.488(15) 1 calc PR A 1 C103 C 0.5000 0.4510(8) 0.7500 0.112(6) Uani 0.488(15) 2 d SPDU . 1 H10F H 0.5019 0.4791 0.8026 0.135 Uiso 0.244(8) 1 calc PR A 1 H10G H 0.4981 0.4791 0.6974 0.135 Uiso 0.244(8) 1 calc PR A 1 C111 C 0.5987(6) 0.4203(9) 0.8279(13) 0.133(6) Uani 0.512(15) 1 d PDU A 2 H11A H 0.6256 0.4552 0.8365 0.200 Uiso 0.512(15) 1 calc PR A 2 H11B H 0.6048 0.3811 0.7992 0.200 Uiso 0.512(15) 1 calc PR A 2 H11C H 0.6064 0.4095 0.8944 0.200 Uiso 0.512(15) 1 calc PR A 2 C112 C 0.5366(6) 0.4435(8) 0.7568(12) 0.175(7) Uani 0.512(15) 1 d PDU . 2 H11D H 0.5294 0.4832 0.7844 0.210 Uiso 0.512(15) 1 calc PR A 2 H11E H 0.5277 0.4542 0.6886 0.210 Uiso 0.512(15) 1 calc PR A 2 C113 C 0.5000 0.3872(5) 0.7500 0.077(4) Uani 0.512(15) 2 d SPDU . 2 H11F H 0.4821 0.3601 0.6873 0.093 Uiso 0.256(8) 1 calc PR A 2 H11G H 0.5179 0.3601 0.8127 0.093 Uiso 0.256(8) 1 calc PR A 2 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 0.0391(4) 0.0536(4) 0.0435(4) -0.0067(3) 0.0209(3) -0.0007(3) B1 0.0393(15) 0.0528(17) 0.0405(15) -0.0008(12) 0.0243(13) 0.0011(13) C1 0.0391(14) 0.0507(15) 0.0481(14) -0.0016(12) 0.0219(12) 0.0013(11) C2 0.0409(14) 0.0538(15) 0.0454(14) -0.0021(12) 0.0237(12) 0.0006(12) C3 0.0496(17) 0.0617(18) 0.0659(19) 0.0116(15) 0.0238(15) 0.0012(14) C4 0.0378(13) 0.0509(15) 0.0453(14) -0.0001(11) 0.0232(12) -0.0002(11) N1 0.0434(12) 0.0597(14) 0.0453(12) -0.0028(10) 0.0267(10) 0.0005(10) C5 0.0593(18) 0.0734(19) 0.0476(15) -0.0069(14) 0.0359(14) 0.0018(15) C6 0.158(4) 0.184(5) 0.104(3) 0.022(3) 0.089(3) 0.101(4) C7 0.086(3) 0.134(4) 0.073(2) -0.041(2) 0.046(2) -0.015(2) C8 0.172(5) 0.142(4) 0.116(3) -0.032(3) 0.120(4) -0.055(3) C11 0.0383(14) 0.0510(15) 0.0549(16) -0.0065(12) 0.0236(12) -0.0043(11) C12 0.0521(16) 0.0517(16) 0.0579(17) -0.0024(13) 0.0300(14) -0.0009(13) F12 0.0941(14) 0.0665(11) 0.0600(10) -0.0009(8) 0.0463(10) 0.0101(10) C13 0.062(2) 0.073(2) 0.0650(19) 0.0092(16) 0.0363(16) -0.0050(16) F13 0.130(2) 0.1041(16) 0.0761(13) 0.0224(12) 0.0645(14) 0.0084(14) C14 0.060(2) 0.060(2) 0.086(2) 0.0196(18) 0.0359(18) -0.0008(15) F14 0.120(2) 0.0748(14) 0.1235(19) 0.0433(13) 0.0642(16) 0.0102(13) C15 0.0568(19) 0.0449(17) 0.098(3) 0.0019(17) 0.0388(19) -0.0005(14) F15 0.1102(18) 0.0493(11) 0.144(2) -0.0014(12) 0.0669(16) 0.0118(11) C16 0.0507(17) 0.0586(18) 0.0660(18) -0.0116(15) 0.0309(15) -0.0018(14) F16 0.1037(16) 0.0686(12) 0.0887(14) -0.0177(10) 0.0554(13) 0.0094(11) C21 0.0388(14) 0.0544(15) 0.0433(13) 0.0002(11) 0.0214(12) 0.0010(11) C22 0.0479(16) 0.0596(17) 0.0485(15) -0.0011(13) 0.0262(13) -0.0009(13) F22 0.0528(10) 0.0736(11) 0.0722(11) -0.0212(9) 0.0293(9) -0.0112(8) C23 0.0384(15) 0.082(2) 0.0573(17) 0.0077(16) 0.0222(14) -0.0012(14) F23 0.0414(10) 0.1113(16) 0.0922(14) -0.0051(12) 0.0228(10) -0.0110(10) C24 0.0480(17) 0.080(2) 0.0640(18) 0.0197(16) 0.0351(15) 0.0182(15) F24 0.0569(12) 0.1151(16) 0.1041(15) 0.0248(13) 0.0486(11) 0.0321(11) C25 0.067(2) 0.0600(18) 0.0606(17) 0.0120(14) 0.0431(16) 0.0209(15) F25 0.0909(14) 0.0780(12) 0.0831(13) 0.0054(10) 0.0558(12) 0.0306(11) C26 0.0491(16) 0.0570(16) 0.0495(15) 0.0001(13) 0.0278(13) 0.0017(13) F26 0.0586(10) 0.0628(10) 0.0702(11) -0.0197(8) 0.0305(9) -0.0008(8) C31 0.0369(13) 0.0600(16) 0.0416(13) 0.0039(12) 0.0211(11) 0.0019(12) C32 0.0445(15) 0.0626(18) 0.0511(15) 0.0025(13) 0.0261(13) -0.0049(13) F32 0.0802(13) 0.0561(10) 0.0836(12) -0.0008(9) 0.0564(11) 0.0032(9) C33 0.0559(18) 0.0572(18) 0.0613(18) 0.0103(14) 0.0217(15) -0.0037(14) F33 0.0947(16) 0.0577(11) 0.0981(15) 0.0118(10) 0.0437(13) -0.0046(10) C34 0.066(2) 0.092(3) 0.069(2) 0.0353(19) 0.0359(18) -0.0017(19) F34 0.122(2) 0.1166(19) 0.1153(18) 0.0556(15) 0.0695(16) -0.0095(15) C35 0.071(2) 0.108(3) 0.064(2) 0.029(2) 0.0465(18) 0.011(2) F35 0.130(2) 0.157(2) 0.1107(17) 0.0536(17) 0.0987(17) 0.0295(18) C36 0.0545(18) 0.082(2) 0.0533(16) 0.0149(15) 0.0339(15) 0.0105(15) F36 0.1019(16) 0.0981(15) 0.0755(12) 0.0154(11) 0.0682(12) 0.0290(12) C41 0.0409(14) 0.0522(15) 0.0463(14) 0.0018(11) 0.0277(12) 0.0004(11) C42 0.0447(15) 0.0552(16) 0.0533(15) -0.0003(13) 0.0268(13) 0.0013(12) F42 0.0473(9) 0.0675(11) 0.0732(11) -0.0192(9) 0.0237(8) -0.0037(8) C43 0.0397(16) 0.080(2) 0.0624(18) 0.0010(16) 0.0219(14) -0.0002(14) F43 0.0419(10) 0.1147(17) 0.0926(14) -0.0208(13) 0.0099(10) 0.0028(10) C44 0.0419(16) 0.077(2) 0.0698(19) 0.0155(16) 0.0324(15) 0.0147(14) F44 0.0533(11) 0.1026(15) 0.1044(15) 0.0212(12) 0.0393(11) 0.0299(11) C45 0.063(2) 0.0634(19) 0.077(2) 0.0026(16) 0.0476(18) 0.0150(15) F45 0.0825(15) 0.0826(14) 0.1199(17) -0.0148(12) 0.0571(14) 0.0259(11) C46 0.0475(16) 0.0633(18) 0.0558(16) -0.0052(14) 0.0289(14) 0.0057(13) F46 0.0607(11) 0.0867(13) 0.0869(13) -0.0376(11) 0.0273(10) 0.0086(10) C101 0.096(6) 0.082(6) 0.075(5) -0.006(4) 0.060(4) 0.002(4) C102 0.159(10) 0.079(6) 0.079(6) 0.024(4) 0.074(6) 0.042(6) C103 0.115(10) 0.140(10) 0.078(7) 0.000 0.052(7) 0.000 C111 0.148(9) 0.143(10) 0.108(8) -0.031(7) 0.073(7) 0.035(7) C112 0.212(12) 0.213(12) 0.133(9) 0.002(7) 0.118(9) 0.027(9) C113 0.096(8) 0.060(5) 0.090(7) 0.000 0.061(6) 0.000 _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 C11 1.842(3) . ? P1 C1 1.853(3) . ? P1 C21 1.856(3) . ? B1 C4 1.623(4) . ? B1 C2 1.632(4) . ? B1 C31 1.635(4) . ? B1 C41 1.651(4) . ? C1 C3 1.539(4) . ? C1 C2 1.541(4) . ? C1 H1 0.9900 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 H3C 0.9700 . ? C4 N1 1.137(3) . ? N1 C5 1.476(3) . ? C5 C6 1.482(5) . ? C5 C8 1.485(5) . ? C5 C7 1.519(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C6 H6C 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 H7C 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C11 C16 1.385(4) . ? C11 C12 1.385(4) . ? C12 F12 1.353(3) . ? C12 C13 1.369(4) . ? C13 F13 1.349(4) . ? C13 C14 1.371(5) . ? C14 F14 1.344(4) . ? C14 C15 1.359(5) . ? C15 F15 1.337(4) . ? C15 C16 1.383(5) . ? C16 F16 1.347(4) . ? C21 C22 1.383(4) . ? C21 C26 1.385(4) . ? C22 F22 1.344(3) . ? C22 C23 1.379(4) . ? C23 F23 1.346(4) . ? C23 C24 1.358(5) . ? C24 F24 1.344(3) . ? C24 C25 1.362(5) . ? C25 F25 1.340(3) . ? C25 C26 1.382(4) . ? C26 F26 1.343(3) . ? C31 C32 1.379(4) . ? C31 C36 1.393(4) . ? C32 F32 1.358(3) . ? C32 C33 1.379(4) . ? C33 F33 1.343(4) . ? C33 C34 1.372(5) . ? C34 F34 1.349(4) . ? C34 C35 1.360(6) . ? C35 F35 1.354(4) . ? C35 C36 1.374(5) . ? C36 F36 1.352(4) . ? C41 C42 1.381(4) . ? C41 C46 1.383(4) . ? C42 F42 1.355(3) . ? C42 C43 1.376(4) . ? C43 F43 1.342(4) . ? C43 C44 1.363(5) . ? C44 F44 1.352(3) . ? C44 C45 1.358(5) . ? C45 F45 1.346(4) . ? C45 C46 1.382(4) . ? C46 F46 1.347(3) . ? C101 C102 1.555(12) . ? C101 H10A 0.9700 . ? C101 H10B 0.9700 . ? C101 H10C 0.9700 . ? C102 C103 1.520(12) . ? C102 H10D 0.9800 . ? C102 H10E 0.9800 . ? C103 C102 1.520(12) 2_656 ? C103 H10F 0.9800 . ? C103 H10G 0.9800 . ? C111 C112 1.480(13) . ? C111 H11A 0.9700 . ? C111 H11B 0.9700 . ? C111 H11C 0.9700 . ? C112 C113 1.474(13) . ? C112 C112 1.89(3) 2_656 ? C112 H11D 0.9800 . ? C112 H11E 0.9800 . ? C113 C112 1.474(13) 2_656 ? C113 H11F 0.9800 . ? C113 H11G 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 C11 P1 C1 103.00(12) . . ? C11 P1 C21 99.91(12) . . ? C1 P1 C21 105.59(12) . . ? C4 B1 C2 105.5(2) . . ? C4 B1 C31 109.3(2) . . ? C2 B1 C31 114.4(2) . . ? C4 B1 C41 103.5(2) . . ? C2 B1 C41 115.3(2) . . ? C31 B1 C41 108.0(2) . . ? C3 C1 C2 113.6(2) . . ? C3 C1 P1 105.54(18) . . ? C2 C1 P1 107.86(18) . . ? C3 C1 H1 109.9 . . ? C2 C1 H1 109.9 . . ? P1 C1 H1 109.9 . . ? C1 C2 B1 115.9(2) . . ? C1 C2 H2A 108.3 . . ? B1 C2 H2A 108.3 . . ? C1 C2 H2B 108.3 . . ? B1 C2 H2B 108.3 . . ? H2A C2 H2B 107.4 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 B1 176.8(3) . . ? C4 N1 C5 172.0(3) . . ? N1 C5 C6 106.7(3) . . ? N1 C5 C8 108.0(3) . . ? C6 C5 C8 115.2(4) . . ? N1 C5 C7 105.1(3) . . ? C6 C5 C7 111.2(4) . . ? C8 C5 C7 110.1(3) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C16 C11 C12 115.0(3) . . ? C16 C11 P1 119.1(2) . . ? C12 C11 P1 125.8(2) . . ? F12 C12 C13 117.6(3) . . ? F12 C12 C11 119.2(2) . . ? C13 C12 C11 123.2(3) . . ? F13 C13 C12 120.3(3) . . ? F13 C13 C14 120.3(3) . . ? C12 C13 C14 119.3(3) . . ? F14 C14 C15 120.2(3) . . ? F14 C14 C13 119.6(4) . . ? C15 C14 C13 120.2(3) . . ? F15 C15 C14 120.2(3) . . ? F15 C15 C16 120.6(4) . . ? C14 C15 C16 119.2(3) . . ? F16 C16 C15 117.1(3) . . ? F16 C16 C11 119.9(3) . . ? C15 C16 C11 122.9(3) . . ? C22 C21 C26 114.9(3) . . ? C22 C21 P1 114.8(2) . . ? C26 C21 P1 129.8(2) . . ? F22 C22 C23 117.3(3) . . ? F22 C22 C21 119.3(3) . . ? C23 C22 C21 123.3(3) . . ? F23 C23 C24 120.7(3) . . ? F23 C23 C22 120.0(3) . . ? C24 C23 C22 119.3(3) . . ? F24 C24 C23 119.8(3) . . ? F24 C24 C25 120.1(3) . . ? C23 C24 C25 120.1(3) . . ? F25 C25 C24 120.7(3) . . ? F25 C25 C26 119.7(3) . . ? C24 C25 C26 119.6(3) . . ? F26 C26 C25 115.8(3) . . ? F26 C26 C21 121.6(2) . . ? C25 C26 C21 122.6(3) . . ? C32 C31 C36 113.5(3) . . ? C32 C31 B1 126.9(2) . . ? C36 C31 B1 119.6(3) . . ? F32 C32 C33 115.3(3) . . ? F32 C32 C31 119.8(2) . . ? C33 C32 C31 124.9(3) . . ? F33 C33 C34 120.7(3) . . ? F33 C33 C32 121.0(3) . . ? C34 C33 C32 118.4(3) . . ? F34 C34 C35 121.0(4) . . ? F34 C34 C33 119.3(4) . . ? C35 C34 C33 119.8(3) . . ? F35 C35 C34 119.9(3) . . ? F35 C35 C36 120.1(4) . . ? C34 C35 C36 120.0(3) . . ? F36 C36 C35 117.2(3) . . ? F36 C36 C31 119.3(3) . . ? C35 C36 C31 123.4(3) . . ? C42 C41 C46 113.5(2) . . ? C42 C41 B1 120.1(2) . . ? C46 C41 B1 126.4(2) . . ? F42 C42 C43 116.5(3) . . ? F42 C42 C41 118.7(2) . . ? C43 C42 C41 124.8(3) . . ? F43 C43 C44 120.2(3) . . ? F43 C43 C42 121.0(3) . . ? C44 C43 C42 118.8(3) . . ? F44 C44 C45 119.8(3) . . ? F44 C44 C43 120.7(3) . . ? C45 C44 C43 119.5(3) . . ? F45 C45 C44 119.7(3) . . ? F45 C45 C46 120.3(3) . . ? C44 C45 C46 119.9(3) . . ? F46 C46 C45 115.6(3) . . ? F46 C46 C41 121.0(3) . . ? C45 C46 C41 123.4(3) . . ? C102 C101 H10A 109.5 . . ? C102 C101 H10B 109.5 . . ? H10A C101 H10B 109.5 . . ? C102 C101 H10C 109.5 . . ? H10A C101 H10C 109.5 . . ? H10B C101 H10C 109.5 . . ? C103 C102 C101 99.6(8) . . ? C103 C102 H10D 111.8 . . ? C101 C102 H10D 111.8 . . ? C103 C102 H10E 111.8 . . ? C101 C102 H10E 111.8 . . ? H10D C102 H10E 109.6 . . ? C102 C103 C102 99.4(14) 2_656 . ? C102 C103 H10F 111.9 2_656 . ? C102 C103 H10F 111.9 . . ? C102 C103 H10G 111.9 2_656 . ? C102 C103 H10G 111.9 . . ? H10F C103 H10G 109.6 . . ? C112 C111 H11A 109.5 . . ? C112 C111 H11B 109.5 . . ? H11A C111 H11B 109.5 . . ? C112 C111 H11C 109.5 . . ? H11A C111 H11C 109.5 . . ? H11B C111 H11C 109.5 . . ? C113 C112 C111 104.7(13) . . ? C113 C112 C112 50.1(7) . 2_656 ? C111 C112 C112 140.6(16) . 2_656 ? C113 C112 H11D 110.8 . . ? C111 C112 H11D 110.8 . . ? C112 C112 H11D 65.3 2_656 . ? C113 C112 H11E 110.8 . . ? C111 C112 H11E 110.8 . . ? C112 C112 H11E 107.1 2_656 . ? H11D C112 H11E 108.9 . . ? C112 C113 C112 79.8(13) 2_656 . ? C112 C113 H11F 115.3 2_656 . ? C112 C113 H11F 115.3 . . ? C112 C113 H11G 115.3 2_656 . ? C112 C113 H11G 115.3 . . ? H11F C113 H11G 112.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 P1 C1 C3 -178.1(2) . . . . ? C21 P1 C1 C3 -73.8(2) . . . . ? C11 P1 C1 C2 60.1(2) . . . . ? C21 P1 C1 C2 164.47(17) . . . . ? C3 C1 C2 B1 76.4(3) . . . . ? P1 C1 C2 B1 -166.98(18) . . . . ? C4 B1 C2 C1 51.7(3) . . . . ? C31 B1 C2 C1 -68.5(3) . . . . ? C41 B1 C2 C1 165.3(2) . . . . ? C2 B1 C4 N1 55(5) . . . . ? C31 B1 C4 N1 178(100) . . . . ? C41 B1 C4 N1 -67(5) . . . . ? B1 C4 N1 C5 164(4) . . . . ? C4 N1 C5 C6 61(2) . . . . ? C4 N1 C5 C8 -174.3(19) . . . . ? C4 N1 C5 C7 -57(2) . . . . ? C1 P1 C11 C16 -121.2(2) . . . . ? C21 P1 C11 C16 130.1(2) . . . . ? C1 P1 C11 C12 55.6(3) . . . . ? C21 P1 C11 C12 -53.1(3) . . . . ? C16 C11 C12 F12 178.6(3) . . . . ? P1 C11 C12 F12 1.6(4) . . . . ? C16 C11 C12 C13 0.6(4) . . . . ? P1 C11 C12 C13 -176.4(2) . . . . ? F12 C12 C13 F13 0.4(5) . . . . ? C11 C12 C13 F13 178.4(3) . . . . ? F12 C12 C13 C14 -178.0(3) . . . . ? C11 C12 C13 C14 0.0(5) . . . . ? F13 C13 C14 F14 0.7(5) . . . . ? C12 C13 C14 F14 179.1(3) . . . . ? F13 C13 C14 C15 -178.9(3) . . . . ? C12 C13 C14 C15 -0.5(5) . . . . ? F14 C14 C15 F15 0.0(5) . . . . ? C13 C14 C15 F15 179.6(3) . . . . ? F14 C14 C15 C16 -179.3(3) . . . . ? C13 C14 C15 C16 0.3(5) . . . . ? F15 C15 C16 F16 0.3(5) . . . . ? C14 C15 C16 F16 179.6(3) . . . . ? F15 C15 C16 C11 -178.9(3) . . . . ? C14 C15 C16 C11 0.4(5) . . . . ? C12 C11 C16 F16 -180.0(3) . . . . ? P1 C11 C16 F16 -2.8(4) . . . . ? C12 C11 C16 C15 -0.8(4) . . . . ? P1 C11 C16 C15 176.4(3) . . . . ? C11 P1 C21 C22 -88.3(2) . . . . ? C1 P1 C21 C22 165.1(2) . . . . ? C11 P1 C21 C26 100.7(3) . . . . ? C1 P1 C21 C26 -5.9(3) . . . . ? C26 C21 C22 F22 -178.8(2) . . . . ? P1 C21 C22 F22 8.8(3) . . . . ? C26 C21 C22 C23 2.6(4) . . . . ? P1 C21 C22 C23 -169.9(2) . . . . ? F22 C22 C23 F23 -1.2(4) . . . . ? C21 C22 C23 F23 177.5(3) . . . . ? F22 C22 C23 C24 -179.6(3) . . . . ? C21 C22 C23 C24 -1.0(5) . . . . ? F23 C23 C24 F24 1.5(5) . . . . ? C22 C23 C24 F24 179.9(3) . . . . ? F23 C23 C24 C25 -179.7(3) . . . . ? C22 C23 C24 C25 -1.3(5) . . . . ? F24 C24 C25 F25 1.2(4) . . . . ? C23 C24 C25 F25 -177.5(3) . . . . ? F24 C24 C25 C26 -179.5(3) . . . . ? C23 C24 C25 C26 1.7(5) . . . . ? F25 C25 C26 F26 -0.6(4) . . . . ? C24 C25 C26 F26 -179.9(3) . . . . ? F25 C25 C26 C21 179.3(2) . . . . ? C24 C25 C26 C21 0.1(4) . . . . ? C22 C21 C26 F26 177.8(2) . . . . ? P1 C21 C26 F26 -11.2(4) . . . . ? C22 C21 C26 C25 -2.1(4) . . . . ? P1 C21 C26 C25 168.9(2) . . . . ? C4 B1 C31 C32 -14.0(4) . . . . ? C2 B1 C31 C32 104.1(3) . . . . ? C41 B1 C31 C32 -126.0(3) . . . . ? C4 B1 C31 C36 166.1(2) . . . . ? C2 B1 C31 C36 -75.8(3) . . . . ? C41 B1 C31 C36 54.2(3) . . . . ? C36 C31 C32 F32 177.1(2) . . . . ? B1 C31 C32 F32 -2.7(4) . . . . ? C36 C31 C32 C33 -1.3(4) . . . . ? B1 C31 C32 C33 178.8(3) . . . . ? F32 C32 C33 F33 0.0(4) . . . . ? C31 C32 C33 F33 178.5(3) . . . . ? F32 C32 C33 C34 -179.3(3) . . . . ? C31 C32 C33 C34 -0.8(5) . . . . ? F33 C33 C34 F34 2.5(5) . . . . ? C32 C33 C34 F34 -178.2(3) . . . . ? F33 C33 C34 C35 -177.0(3) . . . . ? C32 C33 C34 C35 2.3(5) . . . . ? F34 C34 C35 F35 -0.8(6) . . . . ? C33 C34 C35 F35 178.8(3) . . . . ? F34 C34 C35 C36 178.9(3) . . . . ? C33 C34 C35 C36 -1.6(5) . . . . ? F35 C35 C36 F36 -0.6(5) . . . . ? C34 C35 C36 F36 179.7(3) . . . . ? F35 C35 C36 C31 179.0(3) . . . . ? C34 C35 C36 C31 -0.7(5) . . . . ? C32 C31 C36 F36 -178.3(3) . . . . ? B1 C31 C36 F36 1.5(4) . . . . ? C32 C31 C36 C35 2.1(4) . . . . ? B1 C31 C36 C35 -178.1(3) . . . . ? C4 B1 C41 C42 -52.4(3) . . . . ? C2 B1 C41 C42 -167.2(2) . . . . ? C31 B1 C41 C42 63.4(3) . . . . ? C4 B1 C41 C46 129.9(3) . . . . ? C2 B1 C41 C46 15.1(4) . . . . ? C31 B1 C41 C46 -114.3(3) . . . . ? C46 C41 C42 F42 179.5(2) . . . . ? B1 C41 C42 F42 1.5(4) . . . . ? C46 C41 C42 C43 -0.4(4) . . . . ? B1 C41 C42 C43 -178.4(3) . . . . ? F42 C42 C43 F43 0.2(5) . . . . ? C41 C42 C43 F43 -179.9(3) . . . . ? F42 C42 C43 C44 179.9(3) . . . . ? C41 C42 C43 C44 -0.1(5) . . . . ? F43 C43 C44 F44 0.9(5) . . . . ? C42 C43 C44 F44 -178.9(3) . . . . ? F43 C43 C44 C45 179.9(3) . . . . ? C42 C43 C44 C45 0.1(5) . . . . ? F44 C44 C45 F45 0.4(5) . . . . ? C43 C44 C45 F45 -178.6(3) . . . . ? F44 C44 C45 C46 179.4(3) . . . . ? C43 C44 C45 C46 0.4(5) . . . . ? F45 C45 C46 F46 -1.9(4) . . . . ? C44 C45 C46 F46 179.2(3) . . . . ? F45 C45 C46 C41 177.9(3) . . . . ? C44 C45 C46 C41 -1.0(5) . . . . ? C42 C41 C46 F46 -179.2(3) . . . . ? B1 C41 C46 F46 -1.4(4) . . . . ? C42 C41 C46 C45 1.0(4) . . . . ? B1 C41 C46 C45 178.9(3) . . . . ? C101 C102 C103 C102 159.5(9) . . . 2_656 ? C111 C112 C113 C112 145.2(16) . . . 2_656 ? _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 66.95 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.303 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.043 data_erk6820 _database_code_depnum_ccdc_archive 'CCDC 912776' #TrackingRef 'Revision_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H15 B F20 N P' _chemical_formula_weight 835.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 9.1649(2) _cell_length_b 11.6030(2) _cell_length_c 16.2616(4) _cell_angle_alpha 75.1830(10) _cell_angle_beta 75.3750(10) _cell_angle_gamma 85.283(2) _cell_volume 1617.31(6) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4302 _cell_measurement_theta_min 4.08 _cell_measurement_theta_max 28.28 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.715 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 828 _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9103 _exptl_absorpt_correction_T_max 0.9732 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator 'Montel mirror' _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15281 _diffrn_reflns_av_R_equivalents 0.037 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.17 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5516 _reflns_number_gt 4873 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. The n-Butyl isocyanide group is disordered over two positions. Several restraints (SADI, SIMU, ISOR and SAME) were used in order to improve refinement stability. ; _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^)+(0.0362P)^2^+1.1111P] 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 5516 _refine_ls_number_parameters 552 _refine_ls_number_restraints 65 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1200 _refine_ls_wR_factor_gt 0.1141 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.077 _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 0.54100(7) 0.30410(6) 0.26015(4) 0.04759(17) Uani 1 1 d . . . C1 C 0.4567(3) 0.4556(2) 0.25253(15) 0.0471(5) Uani 1 1 d . . . H1 H 0.3680 0.4543 0.3023 0.057 Uiso 1 1 calc R . . C2 C 0.4057(3) 0.4885(2) 0.16565(15) 0.0494(6) Uani 1 1 d . A . H2A H 0.3448 0.4234 0.1648 0.059 Uiso 1 1 calc R . . H2B H 0.4956 0.4936 0.1172 0.059 Uiso 1 1 calc R . . C3 C 0.5747(3) 0.5401(2) 0.25517(18) 0.0586(6) Uani 1 1 d . . . H3A H 0.6536 0.5514 0.2015 0.088 Uiso 1 1 calc R . . H3B H 0.6180 0.5060 0.3049 0.088 Uiso 1 1 calc R . . H3C H 0.5270 0.6164 0.2608 0.088 Uiso 1 1 calc R . . B1 B 0.3086(3) 0.6128(2) 0.14772(17) 0.0455(6) Uani 1 1 d D . . C4 C 0.4233(8) 0.7243(7) 0.1192(8) 0.0472(19) Uani 0.723(9) 1 d PDU A 1 N1 N 0.5142(7) 0.7939(5) 0.0924(4) 0.0610(14) Uani 0.723(9) 1 d PDU A 1 C5 C 0.6370(8) 0.8778(7) 0.0602(4) 0.092(2) Uani 0.723(9) 1 d PD A 1 H5A H 0.5966 0.9586 0.0605 0.110 Uiso 0.723(9) 1 calc PR A 1 H5B H 0.6880 0.8765 -0.0002 0.110 Uiso 0.723(9) 1 calc PR A 1 C6 C 0.7491(5) 0.8457(6) 0.1173(4) 0.0821(18) Uani 0.723(9) 1 d PD A 1 H6A H 0.7779 0.7612 0.1235 0.099 Uiso 0.723(9) 1 calc PR A 1 H6B H 0.8402 0.8926 0.0883 0.099 Uiso 0.723(9) 1 calc PR A 1 C7 C 0.6873(13) 0.8680(9) 0.2068(5) 0.072(2) Uani 0.723(9) 1 d PDU A 1 H7A H 0.5901 0.8287 0.2332 0.087 Uiso 0.723(9) 1 calc PR A 1 H7B H 0.6698 0.9539 0.2011 0.087 Uiso 0.723(9) 1 calc PR A 1 C8 C 0.7924(11) 0.8227(7) 0.2666(7) 0.108(3) Uani 0.723(9) 1 d PDU A 1 H8A H 0.7480 0.8387 0.3234 0.162 Uiso 0.723(9) 1 calc PR A 1 H8B H 0.8881 0.8628 0.2414 0.162 Uiso 0.723(9) 1 calc PR A 1 H8C H 0.8088 0.7375 0.2733 0.162 Uiso 0.723(9) 1 calc PR A 1 C4A C 0.4528(19) 0.7002(17) 0.113(2) 0.046(5) Uani 0.277(9) 1 d PDU A 2 N1A N 0.5570(13) 0.7542(12) 0.0818(10) 0.050(3) Uani 0.277(9) 1 d PDU A 2 C5A C 0.7014(14) 0.8120(12) 0.0497(8) 0.063(4) Uani 0.277(9) 1 d PD A 2 H5A1 H 0.7243 0.8367 -0.0145 0.075 Uiso 0.277(9) 1 calc PR A 2 H5A2 H 0.7800 0.7549 0.0664 0.075 Uiso 0.277(9) 1 calc PR A 2 C6A C 0.7037(17) 0.9192(11) 0.0852(8) 0.074(4) Uani 0.277(9) 1 d PD A 2 H6A1 H 0.8002 0.9588 0.0562 0.089 Uiso 0.277(9) 1 calc PR A 2 H6A2 H 0.6240 0.9749 0.0682 0.089 Uiso 0.277(9) 1 calc PR A 2 C7A C 0.684(3) 0.899(2) 0.1824(11) 0.073(6) Uani 0.277(9) 1 d PDU A 2 H7A1 H 0.5886 0.8576 0.2124 0.088 Uiso 0.277(9) 1 calc PR A 2 H7A2 H 0.6764 0.9761 0.1972 0.088 Uiso 0.277(9) 1 calc PR A 2 C8A C 0.810(3) 0.826(2) 0.2157(14) 0.109(7) Uani 0.277(9) 1 d PDU A 2 H8A1 H 0.7921 0.8177 0.2783 0.163 Uiso 0.277(9) 1 calc PR A 2 H8A2 H 0.9049 0.8666 0.1864 0.163 Uiso 0.277(9) 1 calc PR A 2 H8A3 H 0.8154 0.7482 0.2037 0.163 Uiso 0.277(9) 1 calc PR A 2 C11 C 0.5611(3) 0.2447(2) 0.37407(16) 0.0471(5) Uani 1 1 d . . . F12 F 0.4521(2) 0.40424(14) 0.43784(10) 0.0704(4) Uani 1 1 d . . . C12 C 0.5225(3) 0.2975(2) 0.44423(17) 0.0537(6) Uani 1 1 d . . . F13 F 0.5146(3) 0.29847(18) 0.58978(12) 0.0980(7) Uani 1 1 d . . . C13 C 0.5522(4) 0.2435(3) 0.52451(18) 0.0643(7) Uani 1 1 d . . . F14 F 0.6436(3) 0.07800(17) 0.61620(12) 0.0903(6) Uani 1 1 d . . . C14 C 0.6192(3) 0.1326(3) 0.53753(19) 0.0640(7) Uani 1 1 d . . . F15 F 0.7234(2) -0.03215(15) 0.48263(13) 0.0791(5) Uani 1 1 d . . . C15 C 0.6587(3) 0.0768(2) 0.47068(19) 0.0582(7) Uani 1 1 d . . . F16 F 0.6694(2) 0.07495(15) 0.32638(11) 0.0716(4) Uani 1 1 d . . . C16 C 0.6307(3) 0.1335(2) 0.39067(17) 0.0514(6) Uani 1 1 d . . . C21 C 0.3743(3) 0.2176(2) 0.26889(16) 0.0487(6) Uani 1 1 d . . . F22 F 0.22793(17) 0.27111(15) 0.39571(11) 0.0706(4) Uani 1 1 d . . . C22 C 0.2420(3) 0.2114(2) 0.33365(18) 0.0560(6) Uani 1 1 d . . . F23 F -0.0039(2) 0.1428(2) 0.40251(17) 0.1079(7) Uani 1 1 d . . . C23 C 0.1211(3) 0.1461(3) 0.3381(2) 0.0709(8) Uani 1 1 d . . . F24 F 0.0130(3) 0.0192(2) 0.27918(18) 0.1217(9) Uani 1 1 d . . . C24 C 0.1292(4) 0.0840(3) 0.2762(3) 0.0797(10) Uani 1 1 d . . . F25 F 0.2662(3) 0.02718(18) 0.14884(14) 0.1140(8) Uani 1 1 d U . . C25 C 0.2567(5) 0.0874(3) 0.2107(2) 0.0743(9) Uani 1 1 d . . . F26 F 0.4994(2) 0.15710(16) 0.14019(11) 0.0831(5) Uani 1 1 d . . . C26 C 0.3774(4) 0.1545(2) 0.20725(17) 0.0604(7) Uani 1 1 d . . . C31 C 0.2330(3) 0.6372(2) 0.06279(15) 0.0465(5) Uani 1 1 d . A . F32 F 0.1792(2) 0.83717(14) 0.07247(12) 0.0773(5) Uani 1 1 d . A . C32 C 0.1725(3) 0.7492(2) 0.03242(16) 0.0544(6) Uani 1 1 d . . . F33 F 0.0491(2) 0.89006(16) -0.06244(13) 0.0878(6) Uani 1 1 d . . . C33 C 0.1050(3) 0.7794(2) -0.03701(18) 0.0600(7) Uani 1 1 d . A . F34 F 0.0285(2) 0.72203(18) -0.14799(11) 0.0817(5) Uani 1 1 d . A . C34 C 0.0941(3) 0.6950(3) -0.08045(16) 0.0577(7) Uani 1 1 d . . . F35 F 0.13875(19) 0.49793(16) -0.09417(10) 0.0714(5) Uani 1 1 d . . . C35 C 0.1508(3) 0.5832(3) -0.05358(16) 0.0544(6) Uani 1 1 d . A . F36 F 0.27030(19) 0.44264(14) 0.03700(10) 0.0642(4) Uani 1 1 d . A . C36 C 0.2185(3) 0.5560(2) 0.01625(15) 0.0486(5) Uani 1 1 d . . . C41 C 0.1827(3) 0.6218(2) 0.23641(15) 0.0456(5) Uani 1 1 d . A . F42 F 0.2834(2) 0.78670(15) 0.26249(11) 0.0737(5) Uani 1 1 d . A . C42 C 0.1805(3) 0.6996(2) 0.28872(17) 0.0548(6) Uani 1 1 d . . . F43 F 0.0850(3) 0.7718(2) 0.41576(14) 0.1071(7) Uani 1 1 d . . . C43 C 0.0798(4) 0.6930(3) 0.36858(19) 0.0686(8) Uani 1 1 d . A . F44 F -0.1256(2) 0.5980(2) 0.47687(13) 0.1086(7) Uani 1 1 d . A . C44 C -0.0264(3) 0.6067(3) 0.39934(18) 0.0708(8) Uani 1 1 d . . . F45 F -0.1347(2) 0.4410(2) 0.37985(12) 0.0905(6) Uani 1 1 d . . . C45 C -0.0309(3) 0.5275(3) 0.35044(18) 0.0633(7) Uani 1 1 d . A . F46 F 0.06278(18) 0.45516(15) 0.22612(10) 0.0672(4) Uani 1 1 d . A . C46 C 0.0711(3) 0.5367(2) 0.27110(16) 0.0508(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0421(3) 0.0570(4) 0.0415(3) -0.0103(3) -0.0093(3) 0.0039(3) C1 0.0435(12) 0.0558(14) 0.0401(12) -0.0083(10) -0.0102(10) -0.0004(10) C2 0.0493(13) 0.0580(14) 0.0397(12) -0.0090(11) -0.0118(10) -0.0007(11) C3 0.0561(15) 0.0654(16) 0.0561(15) -0.0100(13) -0.0203(12) -0.0060(12) B1 0.0504(15) 0.0492(14) 0.0382(13) -0.0071(11) -0.0148(11) -0.0064(12) C4 0.054(3) 0.053(4) 0.036(3) -0.009(3) -0.016(3) 0.002(3) N1 0.073(3) 0.063(3) 0.045(3) -0.006(2) -0.015(2) -0.018(3) C5 0.109(5) 0.094(5) 0.063(3) 0.003(3) -0.009(3) -0.057(4) C6 0.055(3) 0.077(4) 0.110(4) -0.020(3) -0.008(3) -0.024(2) C7 0.075(4) 0.053(4) 0.095(5) -0.011(4) -0.039(4) -0.001(3) C8 0.117(5) 0.075(4) 0.166(8) -0.029(5) -0.097(7) 0.009(3) C4A 0.050(8) 0.041(7) 0.044(7) -0.008(6) -0.013(6) 0.008(6) N1A 0.051(6) 0.059(7) 0.038(5) -0.017(5) 0.001(5) -0.013(5) C5A 0.062(7) 0.070(8) 0.054(6) -0.015(6) -0.001(5) -0.028(6) C6A 0.088(9) 0.063(8) 0.070(8) -0.003(6) -0.025(7) -0.016(7) C7A 0.067(8) 0.073(14) 0.084(11) -0.014(10) -0.026(8) -0.015(9) C8A 0.114(13) 0.109(12) 0.110(15) 0.014(12) -0.075(14) -0.016(10) C11 0.0399(12) 0.0538(14) 0.0482(13) -0.0079(11) -0.0153(10) -0.0033(10) F12 0.0920(12) 0.0655(10) 0.0556(9) -0.0197(8) -0.0215(8) 0.0163(9) C12 0.0579(15) 0.0556(15) 0.0492(14) -0.0107(11) -0.0180(12) -0.0008(12) F13 0.160(2) 0.0898(13) 0.0551(10) -0.0244(9) -0.0422(12) 0.0069(13) C13 0.083(2) 0.0663(17) 0.0491(15) -0.0125(13) -0.0251(14) -0.0080(15) F14 0.1286(16) 0.0817(12) 0.0689(11) 0.0044(9) -0.0596(11) -0.0092(11) C14 0.0740(18) 0.0649(17) 0.0579(16) 0.0001(13) -0.0358(14) -0.0141(14) F15 0.0857(12) 0.0588(10) 0.0935(13) -0.0030(9) -0.0414(10) 0.0071(8) C15 0.0535(15) 0.0515(14) 0.0694(18) 0.0001(13) -0.0277(13) -0.0061(11) F16 0.0804(11) 0.0670(10) 0.0717(11) -0.0231(8) -0.0254(9) 0.0178(8) C16 0.0469(13) 0.0557(14) 0.0550(15) -0.0131(12) -0.0182(11) -0.0027(11) C21 0.0551(14) 0.0495(13) 0.0446(13) -0.0094(10) -0.0211(11) 0.0048(11) F22 0.0553(9) 0.0822(11) 0.0733(11) -0.0338(9) 0.0031(8) -0.0067(8) C22 0.0523(15) 0.0582(15) 0.0595(16) -0.0141(12) -0.0179(12) 0.0006(12) F23 0.0530(11) 0.1140(17) 0.146(2) -0.0255(14) -0.0038(12) -0.0219(10) C23 0.0548(17) 0.0683(18) 0.089(2) -0.0097(16) -0.0240(16) -0.0052(14) F24 0.1264(19) 0.0970(15) 0.162(2) -0.0028(15) -0.0870(17) -0.0459(14) C24 0.087(2) 0.0644(19) 0.095(3) 0.0055(17) -0.055(2) -0.0203(17) F25 0.208(3) 0.0790(13) 0.0808(13) -0.0193(10) -0.0741(15) -0.0278(14) C25 0.127(3) 0.0513(16) 0.0613(18) -0.0058(13) -0.059(2) -0.0077(17) F26 0.1226(16) 0.0768(11) 0.0480(9) -0.0227(8) -0.0102(10) 0.0005(10) C26 0.085(2) 0.0538(15) 0.0437(14) -0.0070(11) -0.0256(14) 0.0042(13) C31 0.0486(13) 0.0532(13) 0.0370(12) -0.0081(10) -0.0112(10) -0.0043(10) F32 0.1157(14) 0.0554(9) 0.0765(11) -0.0187(8) -0.0521(10) 0.0085(9) C32 0.0667(16) 0.0553(14) 0.0462(14) -0.0125(11) -0.0214(12) -0.0036(12) F33 0.1168(15) 0.0704(11) 0.0835(13) -0.0044(9) -0.0566(11) 0.0138(10) C33 0.0664(17) 0.0602(16) 0.0513(15) -0.0012(12) -0.0232(13) 0.0001(13) F34 0.0896(12) 0.1068(14) 0.0592(10) -0.0112(9) -0.0454(9) -0.0037(10) C34 0.0561(15) 0.0789(19) 0.0382(13) -0.0061(12) -0.0181(11) -0.0069(13) F35 0.0773(11) 0.0939(12) 0.0544(9) -0.0326(9) -0.0190(8) -0.0097(9) C35 0.0524(14) 0.0750(18) 0.0401(13) -0.0197(12) -0.0102(11) -0.0109(12) F36 0.0828(11) 0.0600(9) 0.0579(9) -0.0219(7) -0.0267(8) 0.0069(8) C36 0.0488(13) 0.0573(14) 0.0377(12) -0.0104(10) -0.0076(10) -0.0028(11) C41 0.0480(13) 0.0508(13) 0.0394(12) -0.0076(10) -0.0179(10) 0.0043(10) F42 0.0908(12) 0.0666(10) 0.0742(11) -0.0293(8) -0.0229(9) -0.0118(9) C42 0.0609(16) 0.0591(15) 0.0495(14) -0.0160(12) -0.0211(12) 0.0041(12) F43 0.1217(17) 0.1328(19) 0.0869(14) -0.0721(14) -0.0190(12) 0.0096(14) C43 0.077(2) 0.084(2) 0.0536(16) -0.0323(15) -0.0211(15) 0.0150(17) F44 0.0891(14) 0.166(2) 0.0608(11) -0.0392(13) 0.0080(10) 0.0099(14) C44 0.0622(18) 0.102(2) 0.0451(15) -0.0235(15) -0.0079(13) 0.0151(17) F45 0.0619(10) 0.1181(16) 0.0752(12) -0.0049(11) 0.0008(9) -0.0237(10) C45 0.0477(15) 0.0804(19) 0.0537(16) -0.0039(14) -0.0098(12) -0.0032(13) F46 0.0661(10) 0.0749(10) 0.0637(10) -0.0211(8) -0.0112(8) -0.0202(8) C46 0.0508(14) 0.0587(15) 0.0459(13) -0.0127(11) -0.0177(11) 0.0015(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C1 1.848(2) . ? P1 C21 1.852(3) . ? P1 C11 1.854(2) . ? C1 C3 1.533(3) . ? C1 C2 1.545(3) . ? C1 H1 0.9900 . ? C2 B1 1.631(4) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 H3C 0.9700 . ? B1 C41 1.625(4) . ? B1 C4A 1.627(12) . ? B1 C4 1.633(6) . ? B1 C31 1.649(3) . ? C4 N1 1.133(6) . ? N1 C5 1.453(6) . ? C5 C6 1.516(8) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C6 C7 1.503(9) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C7 C8 1.509(8) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C4A N1A 1.119(12) . ? N1A C5A 1.446(12) . ? C5A C6A 1.503(13) . ? C5A H5A1 0.9800 . ? C5A H5A2 0.9800 . ? C6A C7A 1.502(14) . ? C6A H6A1 0.9800 . ? C6A H6A2 0.9800 . ? C7A C8A 1.506(14) . ? C7A H7A1 0.9800 . ? C7A H7A2 0.9800 . ? C8A H8A1 0.9700 . ? C8A H8A2 0.9700 . ? C8A H8A3 0.9700 . ? C11 C16 1.385(3) . ? C11 C12 1.386(4) . ? F12 C12 1.340(3) . ? C12 C13 1.380(4) . ? F13 C13 1.333(3) . ? C13 C14 1.370(4) . ? F14 C14 1.340(3) . ? C14 C15 1.362(4) . ? F15 C15 1.341(3) . ? C15 C16 1.376(4) . ? F16 C16 1.348(3) . ? C21 C26 1.378(4) . ? C21 C22 1.384(4) . ? F22 C22 1.339(3) . ? C22 C23 1.369(4) . ? F23 C23 1.339(4) . ? C23 C24 1.365(5) . ? F24 C24 1.338(3) . ? C24 C25 1.364(5) . ? F25 C25 1.347(3) . ? C25 C26 1.385(4) . ? F26 C26 1.347(3) . ? C31 C36 1.383(3) . ? C31 C32 1.390(3) . ? F32 C32 1.356(3) . ? C32 C33 1.377(4) . ? F33 C33 1.346(3) . ? C33 C34 1.368(4) . ? F34 C34 1.339(3) . ? C34 C35 1.364(4) . ? F35 C35 1.347(3) . ? C35 C36 1.383(3) . ? F36 C36 1.350(3) . ? C41 C42 1.386(3) . ? C41 C46 1.388(3) . ? F42 C42 1.352(3) . ? C42 C43 1.378(4) . ? F43 C43 1.345(3) . ? C43 C44 1.364(5) . ? F44 C44 1.341(3) . ? C44 C45 1.369(4) . ? F45 C45 1.350(3) . ? C45 C46 1.374(4) . ? F46 C46 1.352(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 P1 C21 100.81(11) . . ? C1 P1 C11 107.40(11) . . ? C21 P1 C11 97.75(10) . . ? C3 C1 C2 113.3(2) . . ? C3 C1 P1 109.00(17) . . ? C2 C1 P1 105.39(16) . . ? C3 C1 H1 109.7 . . ? C2 C1 H1 109.7 . . ? P1 C1 H1 109.7 . . ? C1 C2 B1 115.8(2) . . ? C1 C2 H2A 108.3 . . ? B1 C2 H2A 108.3 . . ? C1 C2 H2B 108.3 . . ? B1 C2 H2B 108.3 . . ? H2A C2 H2B 107.4 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C41 B1 C4A 119.8(11) . . ? C41 B1 C2 109.80(19) . . ? C4A B1 C2 96.0(9) . . ? C41 B1 C4 109.3(4) . . ? C4A B1 C4 13.6(10) . . ? C2 B1 C4 108.7(4) . . ? C41 B1 C31 111.40(19) . . ? C4A B1 C31 103.8(13) . . ? C2 B1 C31 115.5(2) . . ? C4 B1 C31 101.7(5) . . ? N1 C4 B1 171.3(9) . . ? C4 N1 C5 176.5(8) . . ? N1 C5 C6 110.3(5) . . ? N1 C5 H5A 109.6 . . ? C6 C5 H5A 109.6 . . ? N1 C5 H5B 109.6 . . ? C6 C5 H5B 109.6 . . ? H5A C5 H5B 108.1 . . ? C7 C6 C5 112.7(6) . . ? C7 C6 H6A 109.1 . . ? C5 C6 H6A 109.1 . . ? C7 C6 H6B 109.1 . . ? C5 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? C6 C7 C8 112.3(7) . . ? C6 C7 H7A 109.1 . . ? C8 C7 H7A 109.1 . . ? C6 C7 H7B 109.1 . . ? C8 C7 H7B 109.1 . . ? H7A C7 H7B 107.9 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1A C4A B1 172(3) . . ? C4A N1A C5A 172(2) . . ? N1A C5A C6A 112.2(11) . . ? N1A C5A H5A1 109.2 . . ? C6A C5A H5A1 109.2 . . ? N1A C5A H5A2 109.2 . . ? C6A C5A H5A2 109.2 . . ? H5A1 C5A H5A2 107.9 . . ? C7A C6A C5A 117.6(13) . . ? C7A C6A H6A1 107.9 . . ? C5A C6A H6A1 107.9 . . ? C7A C6A H6A2 107.9 . . ? C5A C6A H6A2 107.9 . . ? H6A1 C6A H6A2 107.2 . . ? C6A C7A C8A 113.4(16) . . ? C6A C7A H7A1 108.9 . . ? C8A C7A H7A1 108.9 . . ? C6A C7A H7A2 108.9 . . ? C8A C7A H7A2 108.9 . . ? H7A1 C7A H7A2 107.7 . . ? C7A C8A H8A1 109.5 . . ? C7A C8A H8A2 109.5 . . ? H8A1 C8A H8A2 109.5 . . ? C7A C8A H8A3 109.5 . . ? H8A1 C8A H8A3 109.5 . . ? H8A2 C8A H8A3 109.5 . . ? C16 C11 C12 115.1(2) . . ? C16 C11 P1 115.43(19) . . ? C12 C11 P1 129.44(19) . . ? F12 C12 C13 116.2(2) . . ? F12 C12 C11 121.4(2) . . ? C13 C12 C11 122.4(2) . . ? F13 C13 C14 119.8(2) . . ? F13 C13 C12 120.3(3) . . ? C14 C13 C12 119.9(3) . . ? F14 C14 C15 120.0(3) . . ? F14 C14 C13 120.2(3) . . ? C15 C14 C13 119.8(2) . . ? F15 C15 C14 120.5(2) . . ? F15 C15 C16 120.3(3) . . ? C14 C15 C16 119.2(2) . . ? F16 C16 C15 117.5(2) . . ? F16 C16 C11 118.9(2) . . ? C15 C16 C11 123.6(2) . . ? C26 C21 C22 115.7(2) . . ? C26 C21 P1 119.5(2) . . ? C22 C21 P1 124.77(19) . . ? F22 C22 C23 117.0(3) . . ? F22 C22 C21 119.9(2) . . ? C23 C22 C21 123.1(3) . . ? F23 C23 C24 120.1(3) . . ? F23 C23 C22 120.6(3) . . ? C24 C23 C22 119.4(3) . . ? F24 C24 C25 119.4(4) . . ? F24 C24 C23 120.6(4) . . ? C25 C24 C23 120.0(3) . . ? F25 C25 C24 120.7(3) . . ? F25 C25 C26 119.6(4) . . ? C24 C25 C26 119.7(3) . . ? F26 C26 C21 120.5(3) . . ? F26 C26 C25 117.4(3) . . ? C21 C26 C25 122.1(3) . . ? C36 C31 C32 113.2(2) . . ? C36 C31 B1 127.2(2) . . ? C32 C31 B1 119.6(2) . . ? F32 C32 C33 116.1(2) . . ? F32 C32 C31 119.2(2) . . ? C33 C32 C31 124.6(2) . . ? F33 C33 C34 119.6(2) . . ? F33 C33 C32 121.0(3) . . ? C34 C33 C32 119.3(2) . . ? F34 C34 C35 120.7(2) . . ? F34 C34 C33 120.5(3) . . ? C35 C34 C33 118.8(2) . . ? F35 C35 C34 119.9(2) . . ? F35 C35 C36 119.7(2) . . ? C34 C35 C36 120.3(2) . . ? F36 C36 C31 121.3(2) . . ? F36 C36 C35 115.1(2) . . ? C31 C36 C35 123.6(2) . . ? C42 C41 C46 113.7(2) . . ? C42 C41 B1 127.1(2) . . ? C46 C41 B1 118.9(2) . . ? F42 C42 C43 116.5(2) . . ? F42 C42 C41 119.6(2) . . ? C43 C42 C41 123.9(3) . . ? F43 C43 C44 120.0(3) . . ? F43 C43 C42 120.4(3) . . ? C44 C43 C42 119.6(3) . . ? F44 C44 C43 120.9(3) . . ? F44 C44 C45 119.7(3) . . ? C43 C44 C45 119.4(3) . . ? F45 C45 C44 120.3(3) . . ? F45 C45 C46 120.2(3) . . ? C44 C45 C46 119.5(3) . . ? F46 C46 C45 117.0(2) . . ? F46 C46 C41 119.0(2) . . ? C45 C46 C41 124.0(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C21 P1 C1 C3 173.64(17) . . . . ? C11 P1 C1 C3 71.88(18) . . . . ? C21 P1 C1 C2 -64.48(17) . . . . ? C11 P1 C1 C2 -166.24(15) . . . . ? C3 C1 C2 B1 -67.9(3) . . . . ? P1 C1 C2 B1 173.03(17) . . . . ? C1 C2 B1 C41 -44.2(3) . . . . ? C1 C2 B1 C4A 80.5(13) . . . . ? C1 C2 B1 C4 75.3(5) . . . . ? C1 C2 B1 C31 -171.1(2) . . . . ? C41 B1 C4 N1 167(7) . . . . ? C4A B1 C4 N1 25(4) . . . . ? C2 B1 C4 N1 47(7) . . . . ? C31 B1 C4 N1 -75(7) . . . . ? B1 C4 N1 C5 -64(19) . . . . ? C4 N1 C5 C6 -27(15) . . . . ? N1 C5 C6 C7 -70.1(9) . . . . ? C5 C6 C7 C8 173.4(7) . . . . ? C41 B1 C4A N1A 180(100) . . . . ? C2 B1 C4A N1A 63(21) . . . . ? C4 B1 C4A N1A -138(27) . . . . ? C31 B1 C4A N1A -55(21) . . . . ? B1 C4A N1A C5A -94(29) . . . . ? C4A N1A C5A C6A -102(14) . . . . ? N1A C5A C6A C7A 64(2) . . . . ? C5A C6A C7A C8A 65(3) . . . . ? C1 P1 C11 C16 -176.56(18) . . . . ? C21 P1 C11 C16 79.5(2) . . . . ? C1 P1 C11 C12 0.3(3) . . . . ? C21 P1 C11 C12 -103.7(2) . . . . ? C16 C11 C12 F12 -178.8(2) . . . . ? P1 C11 C12 F12 4.3(4) . . . . ? C16 C11 C12 C13 0.4(4) . . . . ? P1 C11 C12 C13 -176.5(2) . . . . ? F12 C12 C13 F13 -1.6(4) . . . . ? C11 C12 C13 F13 179.2(3) . . . . ? F12 C12 C13 C14 177.8(3) . . . . ? C11 C12 C13 C14 -1.4(4) . . . . ? F13 C13 C14 F14 1.7(4) . . . . ? C12 C13 C14 F14 -177.7(3) . . . . ? F13 C13 C14 C15 -179.5(3) . . . . ? C12 C13 C14 C15 1.1(4) . . . . ? F14 C14 C15 F15 -0.7(4) . . . . ? C13 C14 C15 F15 -179.5(3) . . . . ? F14 C14 C15 C16 179.0(2) . . . . ? C13 C14 C15 C16 0.2(4) . . . . ? F15 C15 C16 F16 0.6(4) . . . . ? C14 C15 C16 F16 -179.1(2) . . . . ? F15 C15 C16 C11 178.4(2) . . . . ? C14 C15 C16 C11 -1.3(4) . . . . ? C12 C11 C16 F16 178.8(2) . . . . ? P1 C11 C16 F16 -3.9(3) . . . . ? C12 C11 C16 C15 1.0(4) . . . . ? P1 C11 C16 C15 178.3(2) . . . . ? C1 P1 C21 C26 121.3(2) . . . . ? C11 P1 C21 C26 -129.2(2) . . . . ? C1 P1 C21 C22 -58.1(2) . . . . ? C11 P1 C21 C22 51.3(2) . . . . ? C26 C21 C22 F22 -179.1(2) . . . . ? P1 C21 C22 F22 0.3(4) . . . . ? C26 C21 C22 C23 0.8(4) . . . . ? P1 C21 C22 C23 -179.8(2) . . . . ? F22 C22 C23 F23 -0.4(4) . . . . ? C21 C22 C23 F23 179.7(3) . . . . ? F22 C22 C23 C24 179.7(3) . . . . ? C21 C22 C23 C24 -0.2(4) . . . . ? F23 C23 C24 F24 -0.1(5) . . . . ? C22 C23 C24 F24 179.8(3) . . . . ? F23 C23 C24 C25 -180.0(3) . . . . ? C22 C23 C24 C25 -0.1(5) . . . . ? F24 C24 C25 F25 0.5(4) . . . . ? C23 C24 C25 F25 -179.6(3) . . . . ? F24 C24 C25 C26 179.9(2) . . . . ? C23 C24 C25 C26 -0.2(5) . . . . ? C22 C21 C26 F26 178.3(2) . . . . ? P1 C21 C26 F26 -1.1(3) . . . . ? C22 C21 C26 C25 -1.1(4) . . . . ? P1 C21 C26 C25 179.4(2) . . . . ? F25 C25 C26 F26 0.8(4) . . . . ? C24 C25 C26 F26 -178.6(3) . . . . ? F25 C25 C26 C21 -179.8(2) . . . . ? C24 C25 C26 C21 0.9(4) . . . . ? C41 B1 C31 C36 -112.9(3) . . . . ? C4A B1 C31 C36 116.9(9) . . . . ? C2 B1 C31 C36 13.2(4) . . . . ? C4 B1 C31 C36 130.7(4) . . . . ? C41 B1 C31 C32 65.8(3) . . . . ? C4A B1 C31 C32 -64.4(9) . . . . ? C2 B1 C31 C32 -168.1(2) . . . . ? C4 B1 C31 C32 -50.6(4) . . . . ? C36 C31 C32 F32 179.9(2) . . . . ? B1 C31 C32 F32 1.1(4) . . . . ? C36 C31 C32 C33 -0.3(4) . . . . ? B1 C31 C32 C33 -179.1(3) . . . . ? F32 C32 C33 F33 -0.2(4) . . . . ? C31 C32 C33 F33 180.0(3) . . . . ? F32 C32 C33 C34 -179.9(3) . . . . ? C31 C32 C33 C34 0.3(4) . . . . ? F33 C33 C34 F34 0.1(4) . . . . ? C32 C33 C34 F34 179.8(2) . . . . ? F33 C33 C34 C35 -179.7(2) . . . . ? C32 C33 C34 C35 0.0(4) . . . . ? F34 C34 C35 F35 -1.1(4) . . . . ? C33 C34 C35 F35 178.7(2) . . . . ? F34 C34 C35 C36 180.0(2) . . . . ? C33 C34 C35 C36 -0.2(4) . . . . ? C32 C31 C36 F36 -179.7(2) . . . . ? B1 C31 C36 F36 -0.9(4) . . . . ? C32 C31 C36 C35 0.0(4) . . . . ? B1 C31 C36 C35 178.8(2) . . . . ? F35 C35 C36 F36 1.1(3) . . . . ? C34 C35 C36 F36 179.9(2) . . . . ? F35 C35 C36 C31 -178.6(2) . . . . ? C34 C35 C36 C31 0.2(4) . . . . ? C4A B1 C41 C42 1.1(12) . . . . ? C2 B1 C41 C42 110.6(3) . . . . ? C4 B1 C41 C42 -8.5(5) . . . . ? C31 B1 C41 C42 -120.2(3) . . . . ? C4A B1 C41 C46 -171.8(12) . . . . ? C2 B1 C41 C46 -62.3(3) . . . . ? C4 B1 C41 C46 178.5(4) . . . . ? C31 B1 C41 C46 66.9(3) . . . . ? C46 C41 C42 F42 179.9(2) . . . . ? B1 C41 C42 F42 6.7(4) . . . . ? C46 C41 C42 C43 1.2(4) . . . . ? B1 C41 C42 C43 -172.1(2) . . . . ? F42 C42 C43 F43 1.1(4) . . . . ? C41 C42 C43 F43 179.9(3) . . . . ? F42 C42 C43 C44 -179.5(3) . . . . ? C41 C42 C43 C44 -0.8(4) . . . . ? F43 C43 C44 F44 -0.7(5) . . . . ? C42 C43 C44 F44 179.9(3) . . . . ? F43 C43 C44 C45 179.7(3) . . . . ? C42 C43 C44 C45 0.3(5) . . . . ? F44 C44 C45 F45 0.1(4) . . . . ? C43 C44 C45 F45 179.7(3) . . . . ? F44 C44 C45 C46 -179.9(3) . . . . ? C43 C44 C45 C46 -0.3(4) . . . . ? F45 C45 C46 F46 -0.9(4) . . . . ? C44 C45 C46 F46 179.2(2) . . . . ? F45 C45 C46 C41 -179.2(2) . . . . ? C44 C45 C46 C41 0.9(4) . . . . ? C42 C41 C46 F46 -179.5(2) . . . . ? B1 C41 C46 F46 -5.7(3) . . . . ? C42 C41 C46 C45 -1.2(4) . . . . ? B1 C41 C46 C45 172.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.239 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.037 data_erk6428 _database_code_depnum_ccdc_archive 'CCDC 912777' #TrackingRef 'Revision_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H14 B F20 O P' _chemical_formula_weight 884.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 10.7451(3) _cell_length_b 24.4031(8) _cell_length_c 14.3508(6) _cell_angle_alpha 90.00 _cell_angle_beta 110.583(2) _cell_angle_gamma 90.00 _cell_volume 3522.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 5944 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.667 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1752 _exptl_absorpt_coefficient_mu 1.979 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7556 _exptl_absorpt_correction_T_max 0.9250 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ? _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30969 _diffrn_reflns_av_R_equivalents 0.049 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 67.27 _reflns_number_total 6115 _reflns_number_gt 4880 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0549P)^2^+2.7428P] 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 SHELXL _refine_ls_extinction_coef 0.00101(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6115 _refine_ls_number_parameters 534 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0699 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1442 _refine_ls_wR_factor_gt 0.1307 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 0.37985(7) 0.58304(3) 0.04642(5) 0.0480(2) Uani 1 1 d . . . B1 B 0.3740(3) 0.57432(13) -0.2498(2) 0.0496(7) Uani 1 1 d . . . O1 O 0.27613(18) 0.52583(8) -0.30156(14) 0.0524(5) Uani 1 1 d . . . C1 C 0.3032(3) 0.56848(11) -0.0882(2) 0.0491(6) Uani 1 1 d . . . H1 H 0.2404 0.5982 -0.1213 0.059 Uiso 1 1 calc R . . C2 C 0.4167(3) 0.56615(11) -0.1304(2) 0.0493(6) Uani 1 1 d . . . H2A H 0.4613 0.5306 -0.1128 0.059 Uiso 1 1 calc R . . H2B H 0.4819 0.5945 -0.0974 0.059 Uiso 1 1 calc R . . C3 C 0.2279(3) 0.51392(13) -0.0998(2) 0.0636(8) Uani 1 1 d . . . H3A H 0.1772 0.5075 -0.1696 0.095 Uiso 1 1 calc R . . H3B H 0.1679 0.5155 -0.0627 0.095 Uiso 1 1 calc R . . H3C H 0.2910 0.4843 -0.0743 0.095 Uiso 1 1 calc R . . C4 C 0.3150(3) 0.47832(12) -0.3098(2) 0.0550(7) Uani 1 1 d . . . H4 H 0.4068 0.4718 -0.2911 0.066 Uiso 1 1 calc R . . C5 C 0.2270(3) 0.43442(12) -0.3459(2) 0.0552(7) Uani 1 1 d . . . H5 H 0.1346 0.4403 -0.3700 0.066 Uiso 1 1 calc R . . C6 C 0.2757(3) 0.38444(14) -0.3456(3) 0.0663(8) Uani 1 1 d . . . H6 H 0.3682 0.3821 -0.3292 0.080 Uiso 1 1 calc R . . C11 C 0.2391(3) 0.59524(11) 0.0897(2) 0.0480(6) Uani 1 1 d . . . C12 C 0.2664(3) 0.59166(13) 0.1912(2) 0.0563(7) Uani 1 1 d . . . F12 F 0.39395(17) 0.58623(9) 0.25268(13) 0.0802(6) Uani 1 1 d . . . C13 C 0.1710(3) 0.59225(14) 0.2345(2) 0.0637(8) Uani 1 1 d . . . F13 F 0.2043(2) 0.58811(12) 0.33320(14) 0.0990(8) Uani 1 1 d . . . C14 C 0.0400(3) 0.59753(13) 0.1754(2) 0.0592(8) Uani 1 1 d . . . F14 F -0.05369(18) 0.59862(9) 0.21624(15) 0.0812(6) Uani 1 1 d . . . C15 C 0.0074(3) 0.60249(12) 0.0752(2) 0.0536(7) Uani 1 1 d . . . F15 F -0.12041(16) 0.60896(9) 0.01708(14) 0.0746(5) Uani 1 1 d . . . C16 C 0.1046(3) 0.60147(11) 0.0333(2) 0.0497(6) Uani 1 1 d . . . F16 F 0.06344(16) 0.60709(8) -0.06563(12) 0.0625(4) Uani 1 1 d . . . C21 C 0.4448(3) 0.65319(12) 0.0463(2) 0.0523(7) Uani 1 1 d . . . C22 C 0.3719(3) 0.69985(13) 0.0129(3) 0.0690(9) Uani 1 1 d . . . F22 F 0.23813(19) 0.69706(8) -0.0249(2) 0.0982(8) Uani 1 1 d . . . C23 C 0.4294(4) 0.75046(14) 0.0156(4) 0.0899(13) Uani 1 1 d . . . F23 F 0.3524(3) 0.79509(9) -0.0173(3) 0.1418(13) Uani 1 1 d . . . C24 C 0.5650(4) 0.75537(15) 0.0520(4) 0.0896(13) Uani 1 1 d . . . F24 F 0.6205(3) 0.80485(10) 0.0549(3) 0.1353(11) Uani 1 1 d . . . C25 C 0.6412(4) 0.71026(16) 0.0846(3) 0.0790(10) Uani 1 1 d . . . F25 F 0.7738(2) 0.71456(11) 0.1196(2) 0.1184(9) Uani 1 1 d . . . C26 C 0.5820(3) 0.66015(14) 0.0821(2) 0.0617(8) Uani 1 1 d . . . F26 F 0.66156(17) 0.61704(9) 0.11444(16) 0.0802(6) Uani 1 1 d . . . C31 C 0.2859(3) 0.63050(12) -0.2821(2) 0.0564(7) Uani 1 1 d . . . C32 C 0.1493(4) 0.63466(14) -0.3159(3) 0.0751(10) Uani 1 1 d . . . F32 F 0.0729(2) 0.58945(9) -0.3347(2) 0.1136(9) Uani 1 1 d . . . C33 C 0.0796(4) 0.68342(18) -0.3312(4) 0.0943(13) Uani 1 1 d . . . F33 F -0.0524(2) 0.68367(12) -0.3621(3) 0.1425(12) Uani 1 1 d . . . C34 C 0.1484(5) 0.73161(16) -0.3126(4) 0.0949(13) Uani 1 1 d . . . F34 F 0.0837(3) 0.77982(10) -0.3265(3) 0.1381(11) Uani 1 1 d . . . C35 C 0.2835(5) 0.73069(15) -0.2792(3) 0.0864(11) Uani 1 1 d . . . F35 F 0.3533(3) 0.77791(9) -0.2600(3) 0.1259(10) Uani 1 1 d . . . C36 C 0.3482(4) 0.68083(13) -0.2643(3) 0.0702(9) Uani 1 1 d . . . F36 F 0.4832(2) 0.68299(8) -0.2286(2) 0.0998(8) Uani 1 1 d . . . C41 C 0.4944(3) 0.57066(12) -0.2941(2) 0.0518(7) Uani 1 1 d . . . C42 C 0.6278(3) 0.56177(14) -0.2406(2) 0.0627(8) Uani 1 1 d . . . F42 F 0.67230(18) 0.55746(12) -0.14038(14) 0.0943(7) Uani 1 1 d . . . C43 C 0.7234(3) 0.55562(17) -0.2831(3) 0.0739(10) Uani 1 1 d . . . F43 F 0.8511(2) 0.54587(13) -0.22612(18) 0.1099(9) Uani 1 1 d . . . C44 C 0.6883(3) 0.55869(17) -0.3843(3) 0.0751(10) Uani 1 1 d . . . F44 F 0.7803(2) 0.55243(13) -0.42686(18) 0.1104(9) Uani 1 1 d . . . C45 C 0.5588(4) 0.56750(16) -0.4410(2) 0.0714(9) Uani 1 1 d . . . F45 F 0.5228(2) 0.56916(12) -0.54071(15) 0.1082(8) Uani 1 1 d . . . C46 C 0.4659(3) 0.57344(13) -0.3960(2) 0.0597(8) Uani 1 1 d . . . F46 F 0.33891(19) 0.58059(10) -0.45651(13) 0.0847(6) Uani 1 1 d . . . C51 C 0.2044(3) 0.33328(14) -0.3673(3) 0.0709(9) Uani 1 1 d . . . C52 C 0.0665(4) 0.33103(17) -0.3982(3) 0.0895(12) Uani 1 1 d . . . H52 H 0.0168 0.3636 -0.4098 0.107 Uiso 1 1 calc R . . C53 C 0.0033(5) 0.2818(2) -0.4116(5) 0.1251(19) Uani 1 1 d . . . H53 H -0.0899 0.2805 -0.4320 0.150 Uiso 1 1 calc R . . C54 C 0.0761(6) 0.2335(2) -0.3952(5) 0.134(2) Uani 1 1 d . . . H54 H 0.0318 0.1997 -0.4032 0.161 Uiso 1 1 calc R . . C55 C 0.2112(6) 0.23458(19) -0.3677(5) 0.1244(19) Uani 1 1 d . . . H55 H 0.2598 0.2018 -0.3586 0.149 Uiso 1 1 calc R . . C56 C 0.2750(4) 0.28421(15) -0.3535(4) 0.0914(12) Uani 1 1 d . . . H56 H 0.3681 0.2852 -0.3340 0.110 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 0.0450(4) 0.0474(4) 0.0517(4) 0.0022(3) 0.0171(3) 0.0055(3) B1 0.0502(17) 0.0468(17) 0.0503(18) -0.0014(14) 0.0159(14) -0.0027(14) O1 0.0527(11) 0.0502(11) 0.0547(11) -0.0037(9) 0.0195(9) -0.0020(9) C1 0.0503(15) 0.0452(15) 0.0540(16) -0.0004(12) 0.0209(13) 0.0018(12) C2 0.0511(15) 0.0458(15) 0.0524(16) -0.0026(12) 0.0198(13) 0.0013(12) C3 0.070(2) 0.0573(18) 0.070(2) -0.0117(15) 0.0326(17) -0.0139(15) C4 0.0514(16) 0.0572(18) 0.0587(17) -0.0040(14) 0.0221(14) -0.0038(14) C5 0.0528(16) 0.0583(18) 0.0577(17) -0.0048(14) 0.0233(14) -0.0084(14) C6 0.0598(18) 0.068(2) 0.076(2) -0.0157(17) 0.0303(16) -0.0132(16) C11 0.0472(14) 0.0440(15) 0.0510(16) -0.0008(12) 0.0150(12) 0.0017(12) C12 0.0461(15) 0.0666(19) 0.0521(17) -0.0022(14) 0.0122(13) 0.0041(13) F12 0.0516(10) 0.1300(18) 0.0519(10) -0.0015(10) 0.0094(8) 0.0101(10) C13 0.0657(19) 0.080(2) 0.0483(17) -0.0027(15) 0.0231(15) 0.0015(16) F13 0.0818(14) 0.168(2) 0.0511(11) 0.0024(12) 0.0284(10) 0.0105(14) C14 0.0528(17) 0.0655(19) 0.0657(19) -0.0051(15) 0.0286(15) -0.0040(14) F14 0.0641(11) 0.1101(16) 0.0847(13) -0.0066(11) 0.0451(10) -0.0047(11) C15 0.0402(14) 0.0550(16) 0.0625(18) -0.0054(14) 0.0141(13) -0.0022(12) F15 0.0425(9) 0.0978(14) 0.0800(12) -0.0034(11) 0.0172(9) 0.0018(9) C16 0.0490(15) 0.0490(15) 0.0487(16) -0.0026(12) 0.0141(12) 0.0010(12) F16 0.0501(9) 0.0814(12) 0.0516(10) 0.0036(8) 0.0125(7) 0.0093(8) C21 0.0481(15) 0.0542(17) 0.0561(17) -0.0080(13) 0.0203(13) -0.0010(13) C22 0.0545(18) 0.0529(18) 0.103(3) 0.0019(17) 0.0319(18) 0.0031(15) F22 0.0591(11) 0.0597(12) 0.170(2) 0.0295(13) 0.0329(13) 0.0157(9) C23 0.092(3) 0.0442(19) 0.147(4) 0.003(2) 0.059(3) 0.0065(18) F23 0.122(2) 0.0512(13) 0.271(4) 0.0271(18) 0.094(2) 0.0144(13) C24 0.094(3) 0.058(2) 0.133(4) -0.023(2) 0.060(3) -0.027(2) F24 0.132(2) 0.0690(15) 0.226(3) -0.0323(18) 0.089(2) -0.0435(15) C25 0.063(2) 0.076(2) 0.102(3) -0.023(2) 0.034(2) -0.0223(19) F25 0.0655(13) 0.117(2) 0.166(3) -0.0211(18) 0.0332(15) -0.0369(13) C26 0.0563(17) 0.066(2) 0.0644(19) -0.0117(16) 0.0234(15) -0.0031(16) F26 0.0463(9) 0.0871(14) 0.1004(15) 0.0080(11) 0.0173(10) 0.0052(9) C31 0.0613(18) 0.0498(17) 0.0574(17) 0.0049(13) 0.0198(14) 0.0026(14) C32 0.066(2) 0.059(2) 0.093(3) 0.0086(18) 0.0184(19) 0.0046(17) F32 0.0543(11) 0.0741(14) 0.193(3) 0.0013(15) 0.0185(14) 0.0031(10) C33 0.077(3) 0.077(3) 0.120(3) 0.019(2) 0.023(2) 0.027(2) F33 0.0755(16) 0.106(2) 0.223(4) 0.020(2) 0.0242(18) 0.0412(14) C34 0.109(3) 0.057(2) 0.114(3) 0.022(2) 0.034(3) 0.030(2) F34 0.144(2) 0.0697(15) 0.193(3) 0.0296(17) 0.050(2) 0.0496(16) C35 0.103(3) 0.048(2) 0.108(3) 0.0081(19) 0.038(3) 0.003(2) F35 0.144(2) 0.0487(12) 0.187(3) 0.0065(15) 0.061(2) -0.0037(13) C36 0.074(2) 0.0532(19) 0.083(2) 0.0062(16) 0.0262(18) 0.0020(16) F36 0.0790(14) 0.0593(12) 0.156(2) -0.0075(13) 0.0345(14) -0.0132(10) C41 0.0527(16) 0.0517(16) 0.0503(16) -0.0009(13) 0.0170(13) -0.0069(13) C42 0.0573(18) 0.083(2) 0.0483(17) -0.0045(15) 0.0191(14) -0.0083(16) F42 0.0541(10) 0.170(2) 0.0562(11) 0.0014(12) 0.0163(9) 0.0032(12) C43 0.0499(18) 0.103(3) 0.069(2) -0.0084(19) 0.0215(16) -0.0111(18) F43 0.0545(12) 0.186(3) 0.0904(16) -0.0037(16) 0.0268(11) -0.0006(14) C44 0.067(2) 0.099(3) 0.071(2) -0.0126(19) 0.0388(19) -0.0164(19) F44 0.0825(14) 0.178(3) 0.0918(16) -0.0151(16) 0.0569(13) -0.0188(16) C45 0.077(2) 0.089(2) 0.0529(19) -0.0038(17) 0.0288(17) -0.0181(19) F45 0.0963(16) 0.181(3) 0.0548(12) -0.0010(14) 0.0359(11) -0.0160(16) C46 0.0581(17) 0.0658(19) 0.0548(17) -0.0001(14) 0.0193(14) -0.0104(15) F46 0.0670(12) 0.1295(18) 0.0521(10) 0.0105(11) 0.0140(9) 0.0007(12) C51 0.067(2) 0.064(2) 0.086(2) -0.0200(18) 0.0322(18) -0.0178(17) C52 0.074(2) 0.078(3) 0.115(3) -0.032(2) 0.032(2) -0.025(2) C53 0.091(3) 0.095(4) 0.192(6) -0.046(4) 0.053(3) -0.044(3) C54 0.120(4) 0.080(3) 0.202(6) -0.041(4) 0.057(4) -0.045(3) C55 0.118(4) 0.070(3) 0.181(6) -0.034(3) 0.047(4) -0.021(3) C56 0.084(3) 0.063(2) 0.129(4) -0.023(2) 0.039(2) -0.012(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C11 1.849(3) . ? P1 C1 1.849(3) . ? P1 C21 1.849(3) . ? B1 O1 1.584(4) . ? B1 C2 1.622(4) . ? B1 C41 1.632(4) . ? B1 C31 1.638(4) . ? O1 C4 1.252(3) . ? C1 C3 1.537(4) . ? C1 C2 1.542(4) . ? C1 H1 0.9900 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 H3C 0.9700 . ? C4 C5 1.402(4) . ? C4 H4 0.9400 . ? C5 C6 1.326(4) . ? C5 H5 0.9400 . ? C6 C51 1.440(4) . ? C6 H6 0.9400 . ? C11 C12 1.385(4) . ? C11 C16 1.395(4) . ? C12 F12 1.351(3) . ? C12 C13 1.372(4) . ? C13 F13 1.338(4) . ? C13 C14 1.371(4) . ? C14 F14 1.331(3) . ? C14 C15 1.360(4) . ? C15 F15 1.342(3) . ? C15 C16 1.377(4) . ? C16 F16 1.337(3) . ? C21 C22 1.369(4) . ? C21 C26 1.390(4) . ? C22 F22 1.348(4) . ? C22 C23 1.375(5) . ? C23 F23 1.349(4) . ? C23 C24 1.369(6) . ? C24 F24 1.341(4) . ? C24 C25 1.353(6) . ? C25 F25 1.338(4) . ? C25 C26 1.373(5) . ? C26 F26 1.332(4) . ? C31 C32 1.378(5) . ? C31 C36 1.379(4) . ? C32 F32 1.345(4) . ? C32 C33 1.382(5) . ? C33 F33 1.329(5) . ? C33 C34 1.365(6) . ? C34 F34 1.345(4) . ? C34 C35 1.360(6) . ? C35 F35 1.350(4) . ? C35 C36 1.380(5) . ? C36 F36 1.360(4) . ? C41 C42 1.385(4) . ? C41 C46 1.387(4) . ? C42 F42 1.351(4) . ? C42 C43 1.375(4) . ? C43 F43 1.348(4) . ? C43 C44 1.369(5) . ? C44 F44 1.341(4) . ? C44 C45 1.359(5) . ? C45 F45 1.345(4) . ? C45 C46 1.373(4) . ? C46 F46 1.347(4) . ? C51 C52 1.391(5) . ? C51 C56 1.393(5) . ? C52 C53 1.360(6) . ? C52 H52 0.9400 . ? C53 C54 1.388(7) . ? C53 H53 0.9400 . ? C54 C55 1.364(7) . ? C54 H54 0.9400 . ? C55 C56 1.371(6) . ? C55 H55 0.9400 . ? C56 H56 0.9400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 P1 C1 105.38(12) . . ? C11 P1 C21 101.81(12) . . ? C1 P1 C21 101.93(13) . . ? O1 B1 C2 107.4(2) . . ? O1 B1 C41 105.2(2) . . ? C2 B1 C41 115.8(2) . . ? O1 B1 C31 105.7(2) . . ? C2 B1 C31 108.8(2) . . ? C41 B1 C31 113.2(2) . . ? C4 O1 B1 123.2(2) . . ? C3 C1 C2 112.6(2) . . ? C3 C1 P1 107.7(2) . . ? C2 C1 P1 107.12(19) . . ? C3 C1 H1 109.8 . . ? C2 C1 H1 109.8 . . ? P1 C1 H1 109.8 . . ? C1 C2 B1 116.2(2) . . ? C1 C2 H2A 108.2 . . ? B1 C2 H2A 108.2 . . ? C1 C2 H2B 108.2 . . ? B1 C2 H2B 108.2 . . ? H2A C2 H2B 107.4 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O1 C4 C5 122.6(3) . . ? O1 C4 H4 118.7 . . ? C5 C4 H4 118.7 . . ? C6 C5 C4 119.2(3) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C51 128.1(3) . . ? C5 C6 H6 115.9 . . ? C51 C6 H6 115.9 . . ? C12 C11 C16 114.2(3) . . ? C12 C11 P1 116.6(2) . . ? C16 C11 P1 128.7(2) . . ? F12 C12 C13 117.0(3) . . ? F12 C12 C11 118.9(3) . . ? C13 C12 C11 124.1(3) . . ? F13 C13 C14 119.8(3) . . ? F13 C13 C12 120.9(3) . . ? C14 C13 C12 119.3(3) . . ? F14 C14 C15 120.7(3) . . ? F14 C14 C13 120.1(3) . . ? C15 C14 C13 119.3(3) . . ? F15 C15 C14 119.6(3) . . ? F15 C15 C16 119.9(3) . . ? C14 C15 C16 120.5(3) . . ? F16 C16 C15 116.3(2) . . ? F16 C16 C11 121.1(2) . . ? C15 C16 C11 122.6(3) . . ? C22 C21 C26 115.4(3) . . ? C22 C21 P1 126.9(2) . . ? C26 C21 P1 117.7(2) . . ? F22 C22 C21 119.8(3) . . ? F22 C22 C23 117.5(3) . . ? C21 C22 C23 122.8(3) . . ? F23 C23 C24 120.2(3) . . ? F23 C23 C22 120.1(4) . . ? C24 C23 C22 119.8(3) . . ? F24 C24 C25 120.9(4) . . ? F24 C24 C23 119.5(4) . . ? C25 C24 C23 119.6(3) . . ? F25 C25 C24 120.0(3) . . ? F25 C25 C26 120.1(4) . . ? C24 C25 C26 119.8(3) . . ? F26 C26 C25 117.3(3) . . ? F26 C26 C21 120.0(3) . . ? C25 C26 C21 122.7(3) . . ? C32 C31 C36 112.8(3) . . ? C32 C31 B1 126.8(3) . . ? C36 C31 B1 119.9(3) . . ? F32 C32 C31 120.6(3) . . ? F32 C32 C33 114.6(3) . . ? C31 C32 C33 124.8(4) . . ? F33 C33 C34 120.2(4) . . ? F33 C33 C32 120.8(4) . . ? C34 C33 C32 119.0(4) . . ? F34 C34 C35 119.9(4) . . ? F34 C34 C33 120.6(4) . . ? C35 C34 C33 119.5(3) . . ? F35 C35 C34 120.4(4) . . ? F35 C35 C36 120.5(4) . . ? C34 C35 C36 119.1(4) . . ? F36 C36 C31 119.2(3) . . ? F36 C36 C35 115.9(3) . . ? C31 C36 C35 124.9(3) . . ? C42 C41 C46 113.2(3) . . ? C42 C41 B1 126.9(3) . . ? C46 C41 B1 119.8(3) . . ? F42 C42 C43 115.1(3) . . ? F42 C42 C41 120.8(3) . . ? C43 C42 C41 124.1(3) . . ? F43 C43 C44 119.7(3) . . ? F43 C43 C42 120.7(3) . . ? C44 C43 C42 119.6(3) . . ? F44 C44 C45 120.6(3) . . ? F44 C44 C43 120.3(3) . . ? C45 C44 C43 119.1(3) . . ? F45 C45 C44 119.5(3) . . ? F45 C45 C46 120.8(3) . . ? C44 C45 C46 119.7(3) . . ? F46 C46 C45 116.7(3) . . ? F46 C46 C41 118.9(3) . . ? C45 C46 C41 124.3(3) . . ? C52 C51 C56 118.5(3) . . ? C52 C51 C6 121.9(3) . . ? C56 C51 C6 119.5(3) . . ? C53 C52 C51 120.2(4) . . ? C53 C52 H52 119.9 . . ? C51 C52 H52 119.9 . . ? C52 C53 C54 120.1(5) . . ? C52 C53 H53 119.9 . . ? C54 C53 H53 119.9 . . ? C55 C54 C53 120.8(4) . . ? C55 C54 H54 119.6 . . ? C53 C54 H54 119.6 . . ? C54 C55 C56 119.0(5) . . ? C54 C55 H55 120.5 . . ? C56 C55 H55 120.5 . . ? C55 C56 C51 121.3(4) . . ? C55 C56 H56 119.3 . . ? C51 C56 H56 119.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 B1 O1 C4 -78.7(3) . . . . ? C41 B1 O1 C4 45.3(3) . . . . ? C31 B1 O1 C4 165.3(2) . . . . ? C11 P1 C1 C3 -66.5(2) . . . . ? C21 P1 C1 C3 -172.46(19) . . . . ? C11 P1 C1 C2 172.12(18) . . . . ? C21 P1 C1 C2 66.2(2) . . . . ? C3 C1 C2 B1 81.7(3) . . . . ? P1 C1 C2 B1 -160.1(2) . . . . ? O1 B1 C2 C1 -61.7(3) . . . . ? C41 B1 C2 C1 -178.9(2) . . . . ? C31 B1 C2 C1 52.2(3) . . . . ? B1 O1 C4 C5 172.8(3) . . . . ? O1 C4 C5 C6 -175.0(3) . . . . ? C4 C5 C6 C51 171.6(3) . . . . ? C1 P1 C11 C12 162.2(2) . . . . ? C21 P1 C11 C12 -91.8(2) . . . . ? C1 P1 C11 C16 -9.7(3) . . . . ? C21 P1 C11 C16 96.4(3) . . . . ? C16 C11 C12 F12 -179.2(3) . . . . ? P1 C11 C12 F12 7.8(4) . . . . ? C16 C11 C12 C13 2.1(4) . . . . ? P1 C11 C12 C13 -170.9(3) . . . . ? F12 C12 C13 F13 0.6(5) . . . . ? C11 C12 C13 F13 179.4(3) . . . . ? F12 C12 C13 C14 -179.8(3) . . . . ? C11 C12 C13 C14 -1.1(5) . . . . ? F13 C13 C14 F14 0.1(5) . . . . ? C12 C13 C14 F14 -179.5(3) . . . . ? F13 C13 C14 C15 179.1(3) . . . . ? C12 C13 C14 C15 -0.5(5) . . . . ? F14 C14 C15 F15 0.5(5) . . . . ? C13 C14 C15 F15 -178.5(3) . . . . ? F14 C14 C15 C16 179.9(3) . . . . ? C13 C14 C15 C16 0.9(5) . . . . ? F15 C15 C16 F16 -0.1(4) . . . . ? C14 C15 C16 F16 -179.4(3) . . . . ? F15 C15 C16 C11 179.6(3) . . . . ? C14 C15 C16 C11 0.2(5) . . . . ? C12 C11 C16 F16 178.0(3) . . . . ? P1 C11 C16 F16 -10.0(4) . . . . ? C12 C11 C16 C15 -1.6(4) . . . . ? P1 C11 C16 C15 170.3(2) . . . . ? C11 P1 C21 C22 -42.9(3) . . . . ? C1 P1 C21 C22 65.9(3) . . . . ? C11 P1 C21 C26 138.3(2) . . . . ? C1 P1 C21 C26 -113.0(2) . . . . ? C26 C21 C22 F22 178.8(3) . . . . ? P1 C21 C22 F22 -0.1(5) . . . . ? C26 C21 C22 C23 -0.9(5) . . . . ? P1 C21 C22 C23 -179.8(3) . . . . ? F22 C22 C23 F23 1.1(6) . . . . ? C21 C22 C23 F23 -179.2(4) . . . . ? F22 C22 C23 C24 -179.1(4) . . . . ? C21 C22 C23 C24 0.6(7) . . . . ? F23 C23 C24 F24 0.1(7) . . . . ? C22 C23 C24 F24 -179.7(4) . . . . ? F23 C23 C24 C25 -179.9(4) . . . . ? C22 C23 C24 C25 0.3(7) . . . . ? F24 C24 C25 F25 -0.6(7) . . . . ? C23 C24 C25 F25 179.4(4) . . . . ? F24 C24 C25 C26 179.1(4) . . . . ? C23 C24 C25 C26 -0.9(7) . . . . ? F25 C25 C26 F26 -0.8(5) . . . . ? C24 C25 C26 F26 179.5(4) . . . . ? F25 C25 C26 C21 -179.8(3) . . . . ? C24 C25 C26 C21 0.5(6) . . . . ? C22 C21 C26 F26 -178.7(3) . . . . ? P1 C21 C26 F26 0.3(4) . . . . ? C22 C21 C26 C25 0.3(5) . . . . ? P1 C21 C26 C25 179.3(3) . . . . ? O1 B1 C31 C32 20.6(4) . . . . ? C2 B1 C31 C32 -94.5(4) . . . . ? C41 B1 C31 C32 135.2(3) . . . . ? O1 B1 C31 C36 -168.0(3) . . . . ? C2 B1 C31 C36 76.9(4) . . . . ? C41 B1 C31 C36 -53.4(4) . . . . ? C36 C31 C32 F32 -178.4(3) . . . . ? B1 C31 C32 F32 -6.5(6) . . . . ? C36 C31 C32 C33 0.0(6) . . . . ? B1 C31 C32 C33 171.9(4) . . . . ? F32 C32 C33 F33 0.0(6) . . . . ? C31 C32 C33 F33 -178.5(4) . . . . ? F32 C32 C33 C34 178.9(4) . . . . ? C31 C32 C33 C34 0.4(7) . . . . ? F33 C33 C34 F34 -0.9(7) . . . . ? C32 C33 C34 F34 -179.9(4) . . . . ? F33 C33 C34 C35 178.7(4) . . . . ? C32 C33 C34 C35 -0.3(7) . . . . ? F34 C34 C35 F35 -0.1(7) . . . . ? C33 C34 C35 F35 -179.7(4) . . . . ? F34 C34 C35 C36 179.3(4) . . . . ? C33 C34 C35 C36 -0.3(7) . . . . ? C32 C31 C36 F36 178.6(3) . . . . ? B1 C31 C36 F36 6.1(5) . . . . ? C32 C31 C36 C35 -0.7(5) . . . . ? B1 C31 C36 C35 -173.2(4) . . . . ? F35 C35 C36 F36 0.9(6) . . . . ? C34 C35 C36 F36 -178.5(4) . . . . ? F35 C35 C36 C31 -179.7(4) . . . . ? C34 C35 C36 C31 0.8(7) . . . . ? O1 B1 C41 C42 -118.9(3) . . . . ? C2 B1 C41 C42 -0.5(4) . . . . ? C31 B1 C41 C42 126.2(3) . . . . ? O1 B1 C41 C46 57.3(3) . . . . ? C2 B1 C41 C46 175.6(3) . . . . ? C31 B1 C41 C46 -57.7(4) . . . . ? C46 C41 C42 F42 -179.4(3) . . . . ? B1 C41 C42 F42 -3.0(5) . . . . ? C46 C41 C42 C43 -0.7(5) . . . . ? B1 C41 C42 C43 175.7(3) . . . . ? F42 C42 C43 F43 0.2(5) . . . . ? C41 C42 C43 F43 -178.5(3) . . . . ? F42 C42 C43 C44 179.3(3) . . . . ? C41 C42 C43 C44 0.6(6) . . . . ? F43 C43 C44 F44 -0.5(6) . . . . ? C42 C43 C44 F44 -179.6(3) . . . . ? F43 C43 C44 C45 178.8(4) . . . . ? C42 C43 C44 C45 -0.4(6) . . . . ? F44 C44 C45 F45 0.9(6) . . . . ? C43 C44 C45 F45 -178.3(4) . . . . ? F44 C44 C45 C46 179.6(3) . . . . ? C43 C44 C45 C46 0.4(6) . . . . ? F45 C45 C46 F46 0.4(5) . . . . ? C44 C45 C46 F46 -178.3(3) . . . . ? F45 C45 C46 C41 178.1(3) . . . . ? C44 C45 C46 C41 -0.6(6) . . . . ? C42 C41 C46 F46 178.3(3) . . . . ? B1 C41 C46 F46 1.7(4) . . . . ? C42 C41 C46 C45 0.7(5) . . . . ? B1 C41 C46 C45 -175.9(3) . . . . ? C5 C6 C51 C52 3.7(6) . . . . ? C5 C6 C51 C56 -173.7(4) . . . . ? C56 C51 C52 C53 1.8(7) . . . . ? C6 C51 C52 C53 -175.6(4) . . . . ? C51 C52 C53 C54 -0.4(8) . . . . ? C52 C53 C54 C55 -1.4(10) . . . . ? C53 C54 C55 C56 1.9(10) . . . . ? C54 C55 C56 C51 -0.5(9) . . . . ? C52 C51 C56 C55 -1.3(7) . . . . ? C6 C51 C56 C55 176.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 67.27 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.332 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.044 data_erk6441 _database_code_depnum_ccdc_archive 'CCDC 912778' #TrackingRef 'Revision_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H12 B F20 O P' _chemical_formula_weight 858.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.9643(8) _cell_length_b 17.5853(9) _cell_length_c 18.1387(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.951(7) _cell_angle_gamma 90.00 _cell_volume 3496.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 5094 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.630 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 1.973 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7977 _exptl_absorpt_correction_T_max 0.9432 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ? _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23338 _diffrn_reflns_av_R_equivalents 0.071 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.75 _diffrn_reflns_theta_max 66.96 _reflns_number_total 5664 _reflns_number_gt 3593 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. One disordered half molecule of benzene, which could not be refined satisfactorily, was removed using the program SQUEEZE (A.L. Spek, University of Utrecht, Netherlands). The carbon and flourine atoms displayed irregular displacement ellipsoids, which were therefore constrained to be more regular using the program command ISOR. ; loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.500 0.000 181 68 ' ' 2 0.500 1.000 0.500 181 68 ' ' _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^)+(0.1462P)^2^+3.7497P] 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 5664 _refine_ls_number_parameters 515 _refine_ls_number_restraints 324 _refine_ls_R_factor_all 0.1278 _refine_ls_R_factor_gt 0.0905 _refine_ls_wR_factor_ref 0.2799 _refine_ls_wR_factor_gt 0.2536 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.210 _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 0.59867(12) 0.14370(9) 0.20160(9) 0.0628(5) Uani 1 1 d . . . O1 O 0.7814(3) 0.2088(2) 0.1492(2) 0.0667(11) Uani 1 1 d . . . B1 B 0.8841(6) 0.1605(5) 0.1790(4) 0.073(2) Uani 1 1 d . . . C1 C 0.7074(6) 0.0659(4) 0.2002(5) 0.095(2) Uani 1 1 d U . . H1 H 0.7203 0.0557 0.1472 0.114 Uiso 1 1 calc R . . C2 C 0.8254(6) 0.0923(5) 0.2281(5) 0.093(2) Uani 1 1 d U . . H2A H 0.8822 0.0493 0.2293 0.111 Uiso 1 1 calc R . . H2B H 0.8160 0.1103 0.2788 0.111 Uiso 1 1 calc R . . C3 C 0.6950(5) 0.2319(3) 0.1993(3) 0.0624(14) Uani 1 1 d U . . H3 H 0.7338 0.2410 0.2482 0.075 Uiso 1 1 calc R . . C4 C 0.6547(7) -0.0081(4) 0.2304(5) 0.098(2) Uani 1 1 d U . . H4A H 0.7145 -0.0484 0.2261 0.147 Uiso 1 1 calc R . . H4B H 0.5816 -0.0215 0.2024 0.147 Uiso 1 1 calc R . . H4C H 0.6344 -0.0012 0.2818 0.147 Uiso 1 1 calc R . . C11 C 0.4984(5) 0.1347(4) 0.2788(4) 0.0704(16) Uani 1 1 d U . . C12 C 0.5197(6) 0.1711(4) 0.3453(4) 0.0805(18) Uani 1 1 d U . . C13 C 0.4419(9) 0.1667(5) 0.4034(5) 0.098(2) Uani 1 1 d U . . C14 C 0.3387(8) 0.1230(6) 0.3951(6) 0.106(3) Uani 1 1 d U . . C15 C 0.3147(6) 0.0832(6) 0.3326(6) 0.102(3) Uani 1 1 d U . . C16 C 0.3929(6) 0.0892(5) 0.2744(5) 0.085(2) Uani 1 1 d U . . C21 C 0.5028(5) 0.1487(3) 0.1192(4) 0.0656(15) Uani 1 1 d U . . C22 C 0.4054(6) 0.1961(4) 0.1169(4) 0.0760(17) Uani 1 1 d U . . C23 C 0.3385(7) 0.2113(5) 0.0525(5) 0.093(2) Uani 1 1 d U . . C24 C 0.3717(9) 0.1786(6) -0.0109(6) 0.109(3) Uani 1 1 d U . . C25 C 0.4636(9) 0.1295(6) -0.0117(5) 0.101(2) Uani 1 1 d U . . C26 C 0.5309(7) 0.1143(4) 0.0524(4) 0.086(2) Uani 1 1 d U . . C31 C 0.9784(5) 0.2165(4) 0.2265(4) 0.0749(18) Uani 1 1 d U . . C32 C 1.0202(8) 0.2104(5) 0.2997(5) 0.104(3) Uani 1 1 d U . . C33 C 1.1033(8) 0.2623(6) 0.3326(5) 0.097(2) Uani 1 1 d U . . C34 C 1.1449(8) 0.3208(7) 0.2958(7) 0.116(3) Uani 1 1 d U . . C35 C 1.1097(8) 0.3324(6) 0.2267(5) 0.105(2) Uani 1 1 d U . . C36 C 1.0275(6) 0.2792(5) 0.1942(4) 0.089(2) Uani 1 1 d U . . C41 C 0.9559(5) 0.1281(3) 0.1073(4) 0.0632(15) Uani 1 1 d U . . C42 C 1.0654(5) 0.0883(4) 0.1175(4) 0.0715(17) Uani 1 1 d U . . C43 C 1.1366(5) 0.0622(4) 0.0608(4) 0.0730(17) Uani 1 1 d U . . C44 C 1.1016(5) 0.0747(4) -0.0096(4) 0.0762(18) Uani 1 1 d U . . C45 C 0.9946(6) 0.1128(4) -0.0244(4) 0.0742(17) Uani 1 1 d U . . C46 C 0.9243(5) 0.1380(3) 0.0332(4) 0.0665(15) Uani 1 1 d U . . C51 C 0.6262(5) 0.3011(4) 0.1745(4) 0.0668(15) Uani 1 1 d U . . C52 C 0.5640(6) 0.3454(4) 0.2251(4) 0.0762(18) Uani 1 1 d U . . H52 H 0.5675 0.3334 0.2756 0.091 Uiso 1 1 calc R . . C53 C 0.4962(6) 0.4080(4) 0.2003(5) 0.092(2) Uani 1 1 d U . . H53 H 0.4532 0.4378 0.2342 0.110 Uiso 1 1 calc R . . C54 C 0.4923(7) 0.4259(5) 0.1272(6) 0.103(3) Uani 1 1 d U . . H54 H 0.4466 0.4682 0.1111 0.124 Uiso 1 1 calc R . . C55 C 0.5550(7) 0.3828(5) 0.0759(5) 0.102(2) Uani 1 1 d U . . H55 H 0.5515 0.3955 0.0256 0.123 Uiso 1 1 calc R . . C56 C 0.6233(6) 0.3201(4) 0.1004(4) 0.0818(19) Uani 1 1 d U . . H56 H 0.6672 0.2909 0.0665 0.098 Uiso 1 1 calc R . . F12 F 0.6218(4) 0.2132(2) 0.3553(2) 0.0977(13) Uani 1 1 d U . . F13 F 0.4698(6) 0.2033(3) 0.4665(3) 0.1333(19) Uani 1 1 d U . . F14 F 0.2628(6) 0.1180(4) 0.4525(3) 0.155(2) Uani 1 1 d U . . F15 F 0.2159(4) 0.0398(4) 0.3264(3) 0.144(2) Uani 1 1 d U . . F16 F 0.3691(4) 0.0499(3) 0.2138(3) 0.1059(14) Uani 1 1 d U . . F22 F 0.3663(3) 0.2304(2) 0.1780(2) 0.0844(11) Uani 1 1 d U . . F23 F 0.2438(4) 0.2597(3) 0.0524(3) 0.1300(18) Uani 1 1 d U . . F24 F 0.3108(6) 0.1943(4) -0.0747(3) 0.154(2) Uani 1 1 d U . . F25 F 0.4974(6) 0.0938(4) -0.0742(3) 0.147(2) Uani 1 1 d U . . F26 F 0.6217(4) 0.0634(3) 0.0481(3) 0.1132(15) Uani 1 1 d U . . F32 F 0.9837(6) 0.1503(4) 0.3394(3) 0.141(2) Uani 1 1 d U . . F33 F 1.1391(7) 0.2489(4) 0.4040(3) 0.167(3) Uani 1 1 d U . . F34 F 1.2227(6) 0.3699(4) 0.3310(4) 0.161(2) Uani 1 1 d U . . F35 F 1.1484(6) 0.3931(4) 0.1902(4) 0.163(2) Uani 1 1 d U . . F36 F 0.9972(5) 0.2947(3) 0.1238(3) 0.1177(16) Uani 1 1 d U . . F42 F 1.1058(3) 0.0742(2) 0.1875(2) 0.0889(12) Uani 1 1 d U . . F43 F 1.2412(3) 0.0242(3) 0.0759(3) 0.1006(13) Uani 1 1 d U . . F44 F 1.1712(4) 0.0510(3) -0.0656(3) 0.1020(13) Uani 1 1 d U . . F45 F 0.9594(4) 0.1264(3) -0.0944(2) 0.0987(13) Uani 1 1 d U . . F46 F 0.8198(3) 0.1735(2) 0.0134(2) 0.0840(11) Uani 1 1 d U . . 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 0.0428(7) 0.0636(9) 0.0820(11) -0.0061(8) 0.0044(7) 0.0006(6) O1 0.0428(18) 0.087(3) 0.071(3) 0.006(2) 0.0096(17) 0.0122(18) B1 0.046(3) 0.093(5) 0.079(5) 0.013(4) 0.005(3) 0.015(3) C1 0.058(3) 0.076(4) 0.151(6) -0.005(4) -0.001(4) 0.003(3) C2 0.055(3) 0.112(5) 0.111(5) 0.038(4) 0.004(3) -0.001(3) C3 0.046(3) 0.073(4) 0.068(3) -0.002(3) 0.004(2) 0.001(3) C4 0.085(4) 0.072(4) 0.138(6) 0.004(4) 0.004(4) 0.004(4) C11 0.054(3) 0.075(4) 0.083(4) 0.004(3) 0.004(3) -0.002(3) C12 0.080(4) 0.080(4) 0.082(4) 0.004(4) 0.013(3) 0.008(4) C13 0.125(6) 0.088(5) 0.083(5) 0.009(4) 0.020(4) 0.019(5) C14 0.095(5) 0.114(6) 0.110(6) 0.037(5) 0.042(5) 0.019(5) C15 0.060(4) 0.119(6) 0.127(6) 0.042(5) 0.011(4) -0.004(4) C16 0.066(4) 0.094(5) 0.094(5) 0.021(4) 0.004(4) -0.005(3) C21 0.051(3) 0.069(4) 0.076(4) -0.012(3) 0.008(3) -0.004(3) C22 0.059(3) 0.085(4) 0.083(4) -0.001(4) -0.002(3) -0.005(3) C23 0.082(4) 0.094(5) 0.102(5) 0.007(4) -0.010(4) -0.014(4) C24 0.104(5) 0.124(6) 0.098(6) 0.018(5) -0.019(5) -0.036(5) C25 0.116(6) 0.114(6) 0.074(5) -0.016(4) 0.007(4) -0.040(5) C26 0.077(4) 0.087(4) 0.095(5) -0.010(4) 0.018(4) -0.015(4) C31 0.058(3) 0.100(5) 0.067(4) -0.007(3) -0.004(3) 0.022(3) C32 0.100(5) 0.101(5) 0.110(6) 0.004(5) 0.008(5) 0.034(4) C33 0.101(5) 0.110(6) 0.080(5) -0.034(4) -0.035(4) 0.025(5) C34 0.091(5) 0.119(6) 0.138(7) -0.020(6) -0.010(5) 0.007(5) C35 0.096(5) 0.118(6) 0.099(5) -0.013(5) -0.002(4) -0.004(5) C36 0.071(4) 0.114(5) 0.082(5) -0.005(4) -0.010(3) -0.012(4) C41 0.042(3) 0.065(3) 0.083(4) 0.004(3) 0.005(3) -0.001(2) C42 0.051(3) 0.073(4) 0.091(4) 0.000(3) -0.001(3) 0.000(3) C43 0.046(3) 0.070(4) 0.103(5) -0.008(3) 0.005(3) 0.006(3) C44 0.054(3) 0.076(4) 0.099(5) -0.017(4) 0.019(3) -0.008(3) C45 0.066(4) 0.076(4) 0.081(4) 0.001(3) 0.009(3) -0.008(3) C46 0.046(3) 0.068(4) 0.086(4) 0.001(3) 0.002(3) 0.003(3) C51 0.050(3) 0.070(4) 0.081(4) -0.006(3) 0.011(3) 0.001(3) C52 0.063(3) 0.071(4) 0.095(4) -0.012(3) 0.010(3) -0.002(3) C53 0.078(4) 0.079(4) 0.120(6) -0.013(4) 0.025(4) 0.010(3) C54 0.087(5) 0.081(5) 0.142(7) 0.005(5) 0.027(5) 0.025(4) C55 0.095(5) 0.097(5) 0.115(6) 0.022(4) 0.030(4) 0.034(4) C56 0.067(3) 0.078(4) 0.101(5) -0.003(4) 0.020(3) 0.017(3) F12 0.118(3) 0.095(3) 0.080(3) -0.013(2) 0.004(2) -0.021(2) F13 0.211(5) 0.102(3) 0.088(3) 0.005(3) 0.042(3) 0.017(3) F14 0.147(4) 0.178(5) 0.143(4) 0.057(4) 0.086(4) 0.036(4) F15 0.078(3) 0.181(5) 0.174(5) 0.069(4) 0.015(3) -0.036(3) F16 0.082(3) 0.117(3) 0.118(3) 0.019(3) -0.020(2) -0.040(2) F22 0.0614(19) 0.089(3) 0.102(3) -0.007(2) -0.0008(19) 0.0155(18) F23 0.094(3) 0.135(4) 0.159(5) 0.025(3) -0.041(3) 0.010(3) F24 0.166(5) 0.182(5) 0.113(4) 0.030(4) -0.053(4) -0.056(4) F25 0.182(5) 0.176(5) 0.084(3) -0.034(3) 0.028(3) -0.058(4) F26 0.104(3) 0.112(3) 0.125(3) -0.035(3) 0.038(3) 0.001(3) F32 0.189(5) 0.134(4) 0.099(3) 0.008(3) -0.012(3) 0.018(4) F33 0.200(6) 0.175(5) 0.124(4) -0.031(4) -0.062(4) 0.037(5) F34 0.131(4) 0.175(5) 0.175(5) -0.067(4) -0.050(4) -0.008(4) F35 0.149(5) 0.169(5) 0.172(5) -0.019(4) -0.002(4) -0.074(4) F36 0.120(3) 0.137(4) 0.096(3) 0.008(3) -0.001(3) -0.063(3) F42 0.0599(19) 0.101(3) 0.105(3) 0.005(2) -0.0067(19) 0.0186(18) F43 0.058(2) 0.105(3) 0.139(3) -0.016(3) 0.003(2) 0.0246(19) F44 0.081(2) 0.110(3) 0.116(3) -0.029(3) 0.029(2) 0.004(2) F45 0.095(3) 0.119(3) 0.083(3) -0.007(2) 0.011(2) 0.005(2) F46 0.0623(19) 0.106(3) 0.084(2) 0.006(2) -0.0006(17) 0.0192(19) _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 C11 1.801(7) . ? P1 C21 1.815(6) . ? P1 C1 1.815(7) . ? P1 C3 1.878(6) . ? O1 C3 1.386(6) . ? O1 B1 1.504(8) . ? B1 C2 1.632(11) . ? B1 C41 1.634(10) . ? B1 C31 1.658(11) . ? C1 C2 1.456(9) . ? C1 C4 1.529(10) . ? C1 H1 0.9900 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 C51 1.496(9) . ? C3 H3 0.9900 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C4 H4C 0.9700 . ? C11 C12 1.383(10) . ? C11 C16 1.408(9) . ? C12 F12 1.352(8) . ? C12 C13 1.369(10) . ? C13 F13 1.343(10) . ? C13 C14 1.375(13) . ? C14 F14 1.346(9) . ? C14 C15 1.355(13) . ? C15 F15 1.327(9) . ? C15 C16 1.376(11) . ? C16 F16 1.320(9) . ? C21 C22 1.354(9) . ? C21 C26 1.394(10) . ? C22 F22 1.338(8) . ? C22 C23 1.395(11) . ? C23 C24 1.342(13) . ? C23 F23 1.342(10) . ? C24 C25 1.327(13) . ? C24 F24 1.353(10) . ? C25 F25 1.354(10) . ? C25 C26 1.392(12) . ? C26 F26 1.342(9) . ? C31 C36 1.364(10) . ? C31 C32 1.403(11) . ? C32 F32 1.344(11) . ? C32 C33 1.415(13) . ? C33 C34 1.313(13) . ? C33 F33 1.366(10) . ? C34 C35 1.320(13) . ? C34 F34 1.364(11) . ? C35 F35 1.330(11) . ? C35 C36 1.420(12) . ? C36 F36 1.342(9) . ? C41 C46 1.393(9) . ? C41 C42 1.400(8) . ? C42 F42 1.359(8) . ? C42 C43 1.381(9) . ? C43 C44 1.346(10) . ? C43 F43 1.351(7) . ? C44 F44 1.347(7) . ? C44 C45 1.374(9) . ? C45 F45 1.343(8) . ? C45 C46 1.381(9) . ? C46 F46 1.348(6) . ? C51 C56 1.384(10) . ? C51 C52 1.392(9) . ? C52 C53 1.397(10) . ? C52 H52 0.9400 . ? C53 C54 1.364(12) . ? C53 H53 0.9400 . ? C54 C55 1.390(11) . ? C54 H54 0.9400 . ? C55 C56 1.401(10) . ? C55 H55 0.9400 . ? C56 H56 0.9400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 P1 C21 106.9(3) . . ? C11 P1 C1 110.7(4) . . ? C21 P1 C1 113.4(4) . . ? C11 P1 C3 116.1(3) . . ? C21 P1 C3 105.1(3) . . ? C1 P1 C3 104.6(3) . . ? C3 O1 B1 116.5(5) . . ? O1 B1 C2 108.1(5) . . ? O1 B1 C41 106.1(5) . . ? C2 B1 C41 112.2(6) . . ? O1 B1 C31 107.9(6) . . ? C2 B1 C31 113.7(6) . . ? C41 B1 C31 108.4(5) . . ? C2 C1 C4 119.1(7) . . ? C2 C1 P1 109.6(6) . . ? C4 C1 P1 112.5(5) . . ? C2 C1 H1 104.8 . . ? C4 C1 H1 104.8 . . ? P1 C1 H1 104.8 . . ? C1 C2 B1 113.7(6) . . ? C1 C2 H2A 108.8 . . ? B1 C2 H2A 108.8 . . ? C1 C2 H2B 108.8 . . ? B1 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? O1 C3 C51 112.8(5) . . ? O1 C3 P1 99.4(4) . . ? C51 C3 P1 113.4(4) . . ? O1 C3 H3 110.3 . . ? C51 C3 H3 110.3 . . ? P1 C3 H3 110.3 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C12 C11 C16 116.1(6) . . ? C12 C11 P1 122.7(5) . . ? C16 C11 P1 121.2(6) . . ? F12 C12 C13 116.9(7) . . ? F12 C12 C11 119.9(6) . . ? C13 C12 C11 123.2(7) . . ? F13 C13 C12 119.5(9) . . ? F13 C13 C14 122.4(8) . . ? C12 C13 C14 118.0(8) . . ? F14 C14 C15 120.0(10) . . ? F14 C14 C13 118.0(10) . . ? C15 C14 C13 121.9(8) . . ? F15 C15 C14 121.0(8) . . ? F15 C15 C16 119.8(10) . . ? C14 C15 C16 119.2(8) . . ? F16 C16 C15 118.8(7) . . ? F16 C16 C11 119.7(6) . . ? C15 C16 C11 121.5(8) . . ? C22 C21 C26 115.2(6) . . ? C22 C21 P1 120.1(5) . . ? C26 C21 P1 124.1(5) . . ? F22 C22 C21 120.9(6) . . ? F22 C22 C23 115.8(6) . . ? C21 C22 C23 123.2(7) . . ? C24 C23 F23 119.4(8) . . ? C24 C23 C22 119.3(8) . . ? F23 C23 C22 121.2(8) . . ? C25 C24 C23 120.3(9) . . ? C25 C24 F24 119.2(10) . . ? C23 C24 F24 120.5(10) . . ? C24 C25 F25 121.9(9) . . ? C24 C25 C26 120.6(8) . . ? F25 C25 C26 117.4(9) . . ? F26 C26 C25 117.6(7) . . ? F26 C26 C21 121.0(7) . . ? C25 C26 C21 121.4(8) . . ? C36 C31 C32 110.0(7) . . ? C36 C31 B1 120.3(6) . . ? C32 C31 B1 129.6(7) . . ? F32 C32 C31 118.1(9) . . ? F32 C32 C33 118.5(9) . . ? C31 C32 C33 123.3(9) . . ? C34 C33 F33 121.4(9) . . ? C34 C33 C32 121.2(9) . . ? F33 C33 C32 117.4(10) . . ? C33 C34 C35 120.4(10) . . ? C33 C34 F34 118.5(10) . . ? C35 C34 F34 121.2(11) . . ? C34 C35 F35 120.4(9) . . ? C34 C35 C36 117.8(10) . . ? F35 C35 C36 121.9(9) . . ? F36 C36 C31 118.6(6) . . ? F36 C36 C35 114.0(8) . . ? C31 C36 C35 127.4(8) . . ? C46 C41 C42 112.9(6) . . ? C46 C41 B1 127.6(5) . . ? C42 C41 B1 119.5(6) . . ? F42 C42 C43 117.1(5) . . ? F42 C42 C41 118.7(6) . . ? C43 C42 C41 124.3(6) . . ? C44 C43 F43 120.1(6) . . ? C44 C43 C42 119.7(6) . . ? F43 C43 C42 120.2(7) . . ? C43 C44 F44 120.6(6) . . ? C43 C44 C45 119.6(6) . . ? F44 C44 C45 119.8(7) . . ? F45 C45 C44 120.1(6) . . ? F45 C45 C46 120.2(6) . . ? C44 C45 C46 119.6(7) . . ? F46 C46 C45 115.4(6) . . ? F46 C46 C41 120.7(5) . . ? C45 C46 C41 123.8(6) . . ? C56 C51 C52 120.0(6) . . ? C56 C51 C3 119.5(5) . . ? C52 C51 C3 120.4(6) . . ? C51 C52 C53 119.5(7) . . ? C51 C52 H52 120.2 . . ? C53 C52 H52 120.2 . . ? C54 C53 C52 120.2(7) . . ? C54 C53 H53 119.9 . . ? C52 C53 H53 119.9 . . ? C53 C54 C55 121.1(8) . . ? C53 C54 H54 119.4 . . ? C55 C54 H54 119.4 . . ? C54 C55 C56 119.0(8) . . ? C54 C55 H55 120.5 . . ? C56 C55 H55 120.5 . . ? C51 C56 C55 120.1(7) . . ? C51 C56 H56 119.9 . . ? C55 C56 H56 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 O1 B1 C2 48.7(8) . . . . ? C3 O1 B1 C41 169.3(5) . . . . ? C3 O1 B1 C31 -74.7(6) . . . . ? C11 P1 C1 C2 -102.4(6) . . . . ? C21 P1 C1 C2 137.4(6) . . . . ? C3 P1 C1 C2 23.4(7) . . . . ? C11 P1 C1 C4 32.4(7) . . . . ? C21 P1 C1 C4 -87.8(7) . . . . ? C3 P1 C1 C4 158.3(6) . . . . ? C4 C1 C2 B1 167.2(7) . . . . ? P1 C1 C2 B1 -61.3(9) . . . . ? O1 B1 C2 C1 33.6(9) . . . . ? C41 B1 C2 C1 -83.1(8) . . . . ? C31 B1 C2 C1 153.5(6) . . . . ? B1 O1 C3 C51 158.0(5) . . . . ? B1 O1 C3 P1 -81.6(5) . . . . ? C11 P1 C3 O1 162.7(3) . . . . ? C21 P1 C3 O1 -79.4(4) . . . . ? C1 P1 C3 O1 40.3(5) . . . . ? C11 P1 C3 C51 -77.4(5) . . . . ? C21 P1 C3 C51 40.5(5) . . . . ? C1 P1 C3 C51 160.2(5) . . . . ? C21 P1 C11 C12 -141.0(6) . . . . ? C1 P1 C11 C12 95.0(6) . . . . ? C3 P1 C11 C12 -24.1(7) . . . . ? C21 P1 C11 C16 39.2(6) . . . . ? C1 P1 C11 C16 -84.8(6) . . . . ? C3 P1 C11 C16 156.1(5) . . . . ? C16 C11 C12 F12 177.1(6) . . . . ? P1 C11 C12 F12 -2.7(9) . . . . ? C16 C11 C12 C13 -2.6(11) . . . . ? P1 C11 C12 C13 177.7(6) . . . . ? F12 C12 C13 F13 -0.2(11) . . . . ? C11 C12 C13 F13 179.5(7) . . . . ? F12 C12 C13 C14 -178.7(7) . . . . ? C11 C12 C13 C14 0.9(12) . . . . ? F13 C13 C14 F14 0.8(12) . . . . ? C12 C13 C14 F14 179.3(7) . . . . ? F13 C13 C14 C15 -176.5(8) . . . . ? C12 C13 C14 C15 2.0(13) . . . . ? F14 C14 C15 F15 0.9(13) . . . . ? C13 C14 C15 F15 178.3(7) . . . . ? F14 C14 C15 C16 179.7(7) . . . . ? C13 C14 C15 C16 -2.9(13) . . . . ? F15 C15 C16 F16 -1.5(11) . . . . ? C14 C15 C16 F16 179.7(7) . . . . ? F15 C15 C16 C11 179.9(7) . . . . ? C14 C15 C16 C11 1.1(12) . . . . ? C12 C11 C16 F16 -177.0(6) . . . . ? P1 C11 C16 F16 2.7(9) . . . . ? C12 C11 C16 C15 1.5(10) . . . . ? P1 C11 C16 C15 -178.7(6) . . . . ? C11 P1 C21 C22 47.6(6) . . . . ? C1 P1 C21 C22 169.9(5) . . . . ? C3 P1 C21 C22 -76.4(6) . . . . ? C11 P1 C21 C26 -141.7(6) . . . . ? C1 P1 C21 C26 -19.3(7) . . . . ? C3 P1 C21 C26 94.4(6) . . . . ? C26 C21 C22 F22 177.5(6) . . . . ? P1 C21 C22 F22 -10.9(9) . . . . ? C26 C21 C22 C23 -1.2(10) . . . . ? P1 C21 C22 C23 170.3(5) . . . . ? F22 C22 C23 C24 -179.6(7) . . . . ? C21 C22 C23 C24 -0.8(11) . . . . ? F22 C22 C23 F23 2.3(10) . . . . ? C21 C22 C23 F23 -178.9(6) . . . . ? F23 C23 C24 C25 -178.7(8) . . . . ? C22 C23 C24 C25 3.2(13) . . . . ? F23 C23 C24 F24 0.3(12) . . . . ? C22 C23 C24 F24 -177.8(7) . . . . ? C23 C24 C25 F25 178.0(7) . . . . ? F24 C24 C25 F25 -0.9(13) . . . . ? C23 C24 C25 C26 -3.5(13) . . . . ? F24 C24 C25 C26 177.6(7) . . . . ? C24 C25 C26 F26 179.2(7) . . . . ? F25 C25 C26 F26 -2.3(10) . . . . ? C24 C25 C26 C21 1.3(12) . . . . ? F25 C25 C26 C21 179.9(6) . . . . ? C22 C21 C26 F26 -176.8(6) . . . . ? P1 C21 C26 F26 12.0(9) . . . . ? C22 C21 C26 C25 1.0(10) . . . . ? P1 C21 C26 C25 -170.2(6) . . . . ? O1 B1 C31 C36 -55.2(8) . . . . ? C2 B1 C31 C36 -175.2(6) . . . . ? C41 B1 C31 C36 59.3(8) . . . . ? O1 B1 C31 C32 124.8(7) . . . . ? C2 B1 C31 C32 4.8(10) . . . . ? C41 B1 C31 C32 -120.7(7) . . . . ? C36 C31 C32 F32 -178.0(7) . . . . ? B1 C31 C32 F32 2.0(11) . . . . ? C36 C31 C32 C33 -1.2(10) . . . . ? B1 C31 C32 C33 178.8(6) . . . . ? F32 C32 C33 C34 177.9(8) . . . . ? C31 C32 C33 C34 1.1(13) . . . . ? F32 C32 C33 F33 -1.6(11) . . . . ? C31 C32 C33 F33 -178.4(7) . . . . ? F33 C33 C34 C35 179.5(8) . . . . ? C32 C33 C34 C35 0.1(14) . . . . ? F33 C33 C34 F34 -2.0(14) . . . . ? C32 C33 C34 F34 178.5(7) . . . . ? C33 C34 C35 F35 177.5(9) . . . . ? F34 C34 C35 F35 -0.9(15) . . . . ? C33 C34 C35 C36 -0.8(14) . . . . ? F34 C34 C35 C36 -179.2(8) . . . . ? C32 C31 C36 F36 -179.6(7) . . . . ? B1 C31 C36 F36 0.4(10) . . . . ? C32 C31 C36 C35 0.4(11) . . . . ? B1 C31 C36 C35 -179.6(7) . . . . ? C34 C35 C36 F36 -179.4(8) . . . . ? F35 C35 C36 F36 2.3(12) . . . . ? C34 C35 C36 C31 0.6(14) . . . . ? F35 C35 C36 C31 -177.8(8) . . . . ? O1 B1 C41 C46 -4.4(9) . . . . ? C2 B1 C41 C46 113.5(7) . . . . ? C31 B1 C41 C46 -120.1(6) . . . . ? O1 B1 C41 C42 172.5(5) . . . . ? C2 B1 C41 C42 -69.6(7) . . . . ? C31 B1 C41 C42 56.8(8) . . . . ? C46 C41 C42 F42 -179.4(5) . . . . ? B1 C41 C42 F42 3.3(9) . . . . ? C46 C41 C42 C43 1.0(9) . . . . ? B1 C41 C42 C43 -176.3(6) . . . . ? F42 C42 C43 C44 -179.7(6) . . . . ? C41 C42 C43 C44 0.0(10) . . . . ? F42 C42 C43 F43 0.3(9) . . . . ? C41 C42 C43 F43 179.9(6) . . . . ? F43 C43 C44 F44 -1.3(10) . . . . ? C42 C43 C44 F44 178.7(6) . . . . ? F43 C43 C44 C45 179.5(6) . . . . ? C42 C43 C44 C45 -0.6(10) . . . . ? C43 C44 C45 F45 179.3(6) . . . . ? F44 C44 C45 F45 0.0(10) . . . . ? C43 C44 C45 C46 0.1(10) . . . . ? F44 C44 C45 C46 -179.1(6) . . . . ? F45 C45 C46 F46 2.1(9) . . . . ? C44 C45 C46 F46 -178.7(6) . . . . ? F45 C45 C46 C41 -178.2(6) . . . . ? C44 C45 C46 C41 1.0(10) . . . . ? C42 C41 C46 F46 178.3(5) . . . . ? B1 C41 C46 F46 -4.7(10) . . . . ? C42 C41 C46 C45 -1.4(9) . . . . ? B1 C41 C46 C45 175.6(6) . . . . ? O1 C3 C51 C56 20.5(8) . . . . ? P1 C3 C51 C56 -91.5(6) . . . . ? O1 C3 C51 C52 -160.5(5) . . . . ? P1 C3 C51 C52 87.5(6) . . . . ? C56 C51 C52 C53 1.6(10) . . . . ? C3 C51 C52 C53 -177.4(6) . . . . ? C51 C52 C53 C54 -0.8(11) . . . . ? C52 C53 C54 C55 0.1(13) . . . . ? C53 C54 C55 C56 -0.2(13) . . . . ? C52 C51 C56 C55 -1.8(10) . . . . ? C3 C51 C56 C55 177.2(7) . . . . ? C54 C55 C56 C51 1.1(12) . . . . ? _diffrn_measured_fraction_theta_max 0.910 _diffrn_reflns_theta_full 66.96 _diffrn_measured_fraction_theta_full 0.910 _refine_diff_density_max 0.780 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.070 data_erk6559 _database_code_depnum_ccdc_archive 'CCDC 912779' #TrackingRef 'Revision_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H12 B F20 P' _chemical_formula_weight 818.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.6350(4) _cell_length_b 18.8200(7) _cell_length_c 12.7955(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.880(3) _cell_angle_gamma 90.00 _cell_volume 2997.53(17) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 5173 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.813 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 2.237 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6632 _exptl_absorpt_correction_T_max 0.9158 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ? _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25276 _diffrn_reflns_av_R_equivalents 0.043 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.22 _diffrn_reflns_theta_max 67.13 _reflns_number_total 5175 _reflns_number_gt 4252 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. The hydrogen atoms from CH2 group (C7) were refined freely. ; _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^)+(0.0391P)^2^+2.1449P] 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 5175 _refine_ls_number_parameters 497 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1055 _refine_ls_wR_factor_gt 0.0981 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.54731(5) 0.63432(3) 0.74707(5) 0.03603(15) Uani 1 1 d . . . B1 B 0.2927(2) 0.60460(15) 0.6694(2) 0.0390(6) Uani 1 1 d . . . C1 C 0.44034(19) 0.69725(12) 0.75068(19) 0.0396(5) Uani 1 1 d . . . H1 H 0.4085 0.6869 0.8145 0.047 Uiso 1 1 calc R . . C2 C 0.35528(19) 0.67920(13) 0.6522(2) 0.0425(6) Uani 1 1 d . . . H2A H 0.3904 0.6748 0.5899 0.051 Uiso 1 1 calc R . . H2B H 0.3029 0.7179 0.6389 0.051 Uiso 1 1 calc R . . C3 C 0.4781(2) 0.77463(13) 0.7579(2) 0.0504(6) Uani 1 1 d . . . H3A H 0.5037 0.7875 0.6932 0.076 Uiso 1 1 calc R . . H3B H 0.5359 0.7801 0.8179 0.076 Uiso 1 1 calc R . . H3C H 0.4187 0.8053 0.7671 0.076 Uiso 1 1 calc R . . C4 C 0.48836(18) 0.54798(12) 0.73551(18) 0.0372(5) Uani 1 1 d . . . C5 C 0.38089(18) 0.54457(13) 0.71334(18) 0.0387(5) Uani 1 1 d . . . H5 H 0.3519 0.4999 0.7253 0.046 Uiso 1 1 calc R . . C6 C 0.55863(19) 0.48532(13) 0.7686(2) 0.0426(6) Uani 1 1 d . . . C7 C 0.6234(3) 0.45855(19) 0.7066(3) 0.0626(8) Uani 1 1 d . . . H7A H 0.630(3) 0.4814(17) 0.638(3) 0.074(10) Uiso 1 1 d . . . H7B H 0.668(3) 0.4184(18) 0.730(3) 0.074(10) Uiso 1 1 d . . . C8 C 0.5481(3) 0.45383(17) 0.8720(2) 0.0634(8) Uani 1 1 d . . . H8A H 0.5916 0.4111 0.8835 0.095 Uiso 1 1 calc R . . H8B H 0.4735 0.4419 0.8723 0.095 Uiso 1 1 calc R . . H8C H 0.5724 0.4877 0.9281 0.095 Uiso 1 1 calc R . . C11 C 0.64993(19) 0.62989(13) 0.86544(18) 0.0410(6) Uani 1 1 d . . . F12 F 0.53681(13) 0.67690(9) 0.97732(11) 0.0602(4) Uani 1 1 d . . . C12 C 0.6298(2) 0.64679(14) 0.9654(2) 0.0472(6) Uani 1 1 d . . . F13 F 0.68146(17) 0.64983(10) 1.15148(12) 0.0779(5) Uani 1 1 d . . . C13 C 0.7039(3) 0.63214(15) 1.0566(2) 0.0544(7) Uani 1 1 d . . . F14 F 0.86810(16) 0.58299(10) 1.13570(14) 0.0832(6) Uani 1 1 d . . . C14 C 0.7984(2) 0.59907(16) 1.0484(2) 0.0573(8) Uani 1 1 d . . . F15 F 0.91417(13) 0.54988(10) 0.94276(15) 0.0713(5) Uani 1 1 d . . . C15 C 0.8218(2) 0.58177(15) 0.9511(2) 0.0520(7) Uani 1 1 d . . . F16 F 0.77649(12) 0.58139(9) 0.76800(12) 0.0602(4) Uani 1 1 d . . . C16 C 0.7490(2) 0.59800(14) 0.8614(2) 0.0466(6) Uani 1 1 d . . . C21 C 0.61794(19) 0.66106(13) 0.64076(18) 0.0387(5) Uani 1 1 d . . . F22 F 0.72245(12) 0.74562(8) 0.75050(12) 0.0550(4) Uani 1 1 d . . . C22 C 0.69680(19) 0.71356(13) 0.65567(19) 0.0419(6) Uani 1 1 d . . . F23 F 0.82535(13) 0.78545(9) 0.59326(14) 0.0675(5) Uani 1 1 d . . . C23 C 0.7512(2) 0.73445(14) 0.5765(2) 0.0473(6) Uani 1 1 d . . . F24 F 0.77981(14) 0.72204(9) 0.40114(13) 0.0673(5) Uani 1 1 d . . . C24 C 0.7279(2) 0.70246(14) 0.4785(2) 0.0488(6) Uani 1 1 d . . . F25 F 0.62464(17) 0.62218(9) 0.36389(12) 0.0717(5) Uani 1 1 d . . . C25 C 0.6498(2) 0.65153(14) 0.4601(2) 0.0486(6) Uani 1 1 d . . . F26 F 0.52100(14) 0.58057(8) 0.51824(12) 0.0608(4) Uani 1 1 d . . . C26 C 0.5959(2) 0.63110(13) 0.54023(19) 0.0440(6) Uani 1 1 d . . . C31 C 0.21033(19) 0.62177(12) 0.75370(19) 0.0394(5) Uani 1 1 d . . . F32 F 0.29755(13) 0.54992(9) 0.89498(12) 0.0611(4) Uani 1 1 d . . . C32 C 0.2190(2) 0.59712(14) 0.8565(2) 0.0453(6) Uani 1 1 d . . . F33 F 0.16902(16) 0.59219(11) 1.02694(14) 0.0765(5) Uani 1 1 d . . . C33 C 0.1530(2) 0.61760(15) 0.9269(2) 0.0536(7) Uani 1 1 d . . . F34 F 0.00854(15) 0.68726(11) 0.96314(16) 0.0803(6) Uani 1 1 d . . . C34 C 0.0722(2) 0.66484(16) 0.8947(3) 0.0571(8) Uani 1 1 d . . . F35 F -0.02362(14) 0.73608(11) 0.76048(17) 0.0853(6) Uani 1 1 d . . . C35 C 0.0568(2) 0.69010(16) 0.7928(3) 0.0564(7) Uani 1 1 d . . . F36 F 0.10573(12) 0.69591(9) 0.62637(13) 0.0598(4) Uani 1 1 d . . . C36 C 0.1252(2) 0.66831(14) 0.7257(2) 0.0467(6) Uani 1 1 d . . . C41 C 0.22025(19) 0.56893(13) 0.56192(19) 0.0412(5) Uani 1 1 d . . . F42 F 0.17737(12) 0.46982(8) 0.66197(12) 0.0546(4) Uani 1 1 d . . . C42 C 0.17122(19) 0.50330(14) 0.5670(2) 0.0453(6) Uani 1 1 d . . . F43 F 0.06974(13) 0.40366(8) 0.49410(15) 0.0656(5) Uani 1 1 d . . . C43 C 0.1129(2) 0.46782(14) 0.4817(2) 0.0494(6) Uani 1 1 d . . . F44 F 0.03830(13) 0.46714(10) 0.29973(13) 0.0691(5) Uani 1 1 d . . . C44 C 0.0973(2) 0.49952(16) 0.3835(2) 0.0514(7) Uani 1 1 d . . . F45 F 0.12757(14) 0.59643(10) 0.27688(12) 0.0646(4) Uani 1 1 d . . . C45 C 0.1412(2) 0.56493(15) 0.3731(2) 0.0489(6) Uani 1 1 d . . . F46 F 0.24081(13) 0.66279(8) 0.44187(12) 0.0587(4) Uani 1 1 d . . . C46 C 0.2007(2) 0.59801(13) 0.4605(2) 0.0448(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0329(3) 0.0382(3) 0.0372(3) -0.0011(2) 0.0068(2) -0.0022(3) B1 0.0324(13) 0.0380(14) 0.0460(15) 0.0000(12) 0.0046(11) -0.0022(12) C1 0.0376(12) 0.0361(12) 0.0464(13) -0.0017(10) 0.0108(10) -0.0023(10) C2 0.0362(13) 0.0405(14) 0.0501(14) 0.0048(11) 0.0053(11) 0.0013(11) C3 0.0486(15) 0.0391(14) 0.0643(17) -0.0029(12) 0.0115(13) -0.0021(12) C4 0.0356(12) 0.0388(13) 0.0380(12) -0.0008(10) 0.0084(10) 0.0002(10) C5 0.0370(13) 0.0372(12) 0.0425(13) -0.0003(10) 0.0084(10) -0.0003(10) C6 0.0345(12) 0.0383(13) 0.0535(14) -0.0018(11) 0.0037(11) 0.0000(11) C7 0.0563(18) 0.066(2) 0.068(2) -0.0008(16) 0.0165(15) 0.0192(16) C8 0.0650(19) 0.0602(18) 0.0671(19) 0.0230(15) 0.0173(15) 0.0161(15) C11 0.0392(13) 0.0441(14) 0.0395(13) -0.0008(11) 0.0062(10) -0.0070(11) F12 0.0667(10) 0.0707(11) 0.0463(8) -0.0050(7) 0.0187(7) 0.0045(9) C12 0.0508(16) 0.0461(15) 0.0448(14) 0.0006(11) 0.0088(12) -0.0053(12) F13 0.1110(15) 0.0829(13) 0.0376(9) -0.0019(8) 0.0066(9) -0.0115(11) C13 0.072(2) 0.0528(16) 0.0360(14) 0.0015(12) 0.0035(13) -0.0196(15) F14 0.0883(13) 0.0826(13) 0.0634(11) 0.0183(9) -0.0300(10) -0.0125(11) C14 0.0581(18) 0.0524(16) 0.0539(17) 0.0129(13) -0.0118(14) -0.0142(14) F15 0.0423(9) 0.0722(11) 0.0927(13) 0.0139(10) -0.0074(8) 0.0038(8) C15 0.0390(14) 0.0485(15) 0.0639(18) 0.0079(13) -0.0043(12) -0.0053(12) F16 0.0446(8) 0.0795(11) 0.0573(9) 0.0005(8) 0.0107(7) 0.0131(8) C16 0.0403(13) 0.0499(15) 0.0481(15) 0.0027(12) 0.0032(11) -0.0021(12) C21 0.0377(13) 0.0385(13) 0.0407(13) -0.0025(10) 0.0092(10) -0.0015(10) F22 0.0560(9) 0.0562(9) 0.0510(8) -0.0058(7) 0.0045(7) -0.0186(7) C22 0.0399(13) 0.0421(13) 0.0439(13) 0.0007(11) 0.0075(10) -0.0018(11) F23 0.0509(9) 0.0681(11) 0.0828(11) 0.0180(9) 0.0100(8) -0.0215(8) C23 0.0371(13) 0.0463(15) 0.0589(16) 0.0116(12) 0.0094(11) -0.0022(12) F24 0.0714(11) 0.0709(11) 0.0696(10) 0.0233(9) 0.0403(9) 0.0102(9) C24 0.0510(15) 0.0471(15) 0.0540(16) 0.0147(12) 0.0247(12) 0.0110(13) F25 0.1099(15) 0.0654(11) 0.0460(9) -0.0084(8) 0.0310(9) -0.0036(10) C25 0.0632(17) 0.0459(15) 0.0399(14) -0.0006(11) 0.0184(12) 0.0049(13) F26 0.0796(11) 0.0578(10) 0.0460(8) -0.0105(7) 0.0134(8) -0.0256(9) C26 0.0483(14) 0.0400(13) 0.0447(14) -0.0009(11) 0.0109(11) -0.0041(12) C31 0.0334(12) 0.0365(13) 0.0478(14) -0.0032(10) 0.0052(10) -0.0030(10) F32 0.0619(10) 0.0660(10) 0.0567(9) 0.0156(8) 0.0138(8) 0.0126(8) C32 0.0401(14) 0.0417(14) 0.0545(15) -0.0020(12) 0.0093(11) -0.0028(11) F33 0.0892(13) 0.0873(13) 0.0598(10) 0.0019(9) 0.0319(9) -0.0142(11) C33 0.0529(16) 0.0568(17) 0.0544(16) -0.0067(13) 0.0188(13) -0.0146(14) F34 0.0676(11) 0.0839(13) 0.1009(14) -0.0314(11) 0.0469(10) -0.0130(10) C34 0.0455(15) 0.0585(17) 0.074(2) -0.0228(15) 0.0277(14) -0.0112(14) F35 0.0545(10) 0.0888(14) 0.1125(15) -0.0124(12) 0.0137(10) 0.0313(10) C35 0.0347(14) 0.0537(17) 0.080(2) -0.0154(15) 0.0076(13) 0.0027(13) F36 0.0517(9) 0.0609(10) 0.0626(10) 0.0022(8) -0.0018(7) 0.0145(8) C36 0.0387(14) 0.0445(14) 0.0556(16) -0.0066(12) 0.0051(11) 0.0003(11) C41 0.0346(12) 0.0408(13) 0.0484(14) -0.0024(11) 0.0079(10) 0.0031(10) F42 0.0478(8) 0.0506(9) 0.0640(9) 0.0075(7) 0.0060(7) -0.0107(7) C42 0.0364(13) 0.0443(14) 0.0551(15) -0.0008(12) 0.0072(11) 0.0013(11) F43 0.0499(9) 0.0512(9) 0.0939(13) -0.0155(9) 0.0076(8) -0.0118(8) C43 0.0352(13) 0.0436(15) 0.0694(18) -0.0133(13) 0.0087(12) -0.0041(11) F44 0.0488(9) 0.0854(12) 0.0689(10) -0.0335(9) -0.0013(8) 0.0000(9) C44 0.0350(13) 0.0612(18) 0.0568(16) -0.0222(14) 0.0043(12) 0.0020(13) F45 0.0641(10) 0.0806(12) 0.0462(9) -0.0015(8) 0.0010(7) 0.0143(9) C45 0.0414(14) 0.0598(17) 0.0444(14) -0.0040(12) 0.0040(11) 0.0100(13) F46 0.0675(10) 0.0528(9) 0.0529(9) 0.0094(7) 0.0022(7) -0.0044(8) C46 0.0408(13) 0.0422(14) 0.0512(15) -0.0011(12) 0.0076(11) 0.0021(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C4 1.783(2) . ? P1 C1 1.804(2) . ? P1 C11 1.819(2) . ? P1 C21 1.821(2) . ? B1 C5 1.618(4) . ? B1 C2 1.644(4) . ? B1 C31 1.654(4) . ? B1 C41 1.658(4) . ? C1 C3 1.530(3) . ? C1 C2 1.547(3) . ? C1 H1 0.9900 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 H3C 0.9700 . ? C4 C5 1.340(3) . ? C4 C6 1.493(3) . ? C5 H5 0.9400 . ? C6 C7 1.332(4) . ? C6 C8 1.476(4) . ? C7 H7A 0.99(3) . ? C7 H7B 0.96(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C11 C12 1.383(4) . ? C11 C16 1.397(4) . ? F12 C12 1.337(3) . ? C12 C13 1.393(4) . ? F13 C13 1.335(3) . ? C13 C14 1.366(4) . ? F14 C14 1.333(3) . ? C14 C15 1.368(4) . ? F15 C15 1.332(3) . ? C15 C16 1.376(4) . ? F16 C16 1.338(3) . ? C21 C26 1.388(3) . ? C21 C22 1.393(3) . ? F22 C22 1.344(3) . ? C22 C23 1.375(4) . ? F23 C23 1.333(3) . ? C23 C24 1.377(4) . ? F24 C24 1.330(3) . ? C24 C25 1.367(4) . ? F25 C25 1.337(3) . ? C25 C26 1.379(4) . ? F26 C26 1.337(3) . ? C31 C32 1.381(3) . ? C31 C36 1.386(4) . ? F32 C32 1.360(3) . ? C32 C33 1.384(4) . ? F33 C33 1.349(3) . ? C33 C34 1.363(4) . ? F34 C34 1.354(3) . ? C34 C35 1.370(4) . ? F35 C35 1.345(3) . ? C35 C36 1.382(4) . ? F36 C36 1.355(3) . ? C41 C42 1.388(4) . ? C41 C46 1.391(4) . ? F42 C42 1.359(3) . ? C42 C43 1.380(4) . ? F43 C43 1.346(3) . ? C43 C44 1.374(4) . ? F44 C44 1.343(3) . ? C44 C45 1.366(4) . ? F45 C45 1.350(3) . ? C45 C46 1.384(4) . ? F46 C46 1.357(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 P1 C1 107.24(11) . . ? C4 P1 C11 104.79(11) . . ? C1 P1 C11 116.04(11) . . ? C4 P1 C21 116.18(11) . . ? C1 P1 C21 107.64(11) . . ? C11 P1 C21 105.30(11) . . ? C5 B1 C2 108.93(19) . . ? C5 B1 C31 112.5(2) . . ? C2 B1 C31 106.9(2) . . ? C5 B1 C41 104.75(19) . . ? C2 B1 C41 116.4(2) . . ? C31 B1 C41 107.47(19) . . ? C3 C1 C2 115.1(2) . . ? C3 C1 P1 113.52(17) . . ? C2 C1 P1 104.70(16) . . ? C3 C1 H1 107.7 . . ? C2 C1 H1 107.7 . . ? P1 C1 H1 107.7 . . ? C1 C2 B1 111.16(19) . . ? C1 C2 H2A 109.4 . . ? B1 C2 H2A 109.4 . . ? C1 C2 H2B 109.4 . . ? B1 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C5 C4 C6 123.6(2) . . ? C5 C4 P1 117.05(18) . . ? C6 C4 P1 118.47(17) . . ? C4 C5 B1 130.7(2) . . ? C4 C5 H5 114.6 . . ? B1 C5 H5 114.6 . . ? C7 C6 C8 122.7(3) . . ? C7 C6 C4 121.7(3) . . ? C8 C6 C4 115.5(2) . . ? C6 C7 H7A 120.7(19) . . ? C6 C7 H7B 120(2) . . ? H7A C7 H7B 119(3) . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C12 C11 C16 116.1(2) . . ? C12 C11 P1 122.8(2) . . ? C16 C11 P1 120.28(19) . . ? F12 C12 C11 120.5(2) . . ? F12 C12 C13 117.8(2) . . ? C11 C12 C13 121.7(3) . . ? F13 C13 C14 120.6(3) . . ? F13 C13 C12 119.7(3) . . ? C14 C13 C12 119.8(3) . . ? F14 C14 C13 120.0(3) . . ? F14 C14 C15 119.6(3) . . ? C13 C14 C15 120.4(2) . . ? F15 C15 C14 120.6(2) . . ? F15 C15 C16 120.2(3) . . ? C14 C15 C16 119.2(3) . . ? F16 C16 C15 117.0(2) . . ? F16 C16 C11 120.3(2) . . ? C15 C16 C11 122.7(3) . . ? C26 C21 C22 116.1(2) . . ? C26 C21 P1 122.25(18) . . ? C22 C21 P1 121.63(18) . . ? F22 C22 C23 117.6(2) . . ? F22 C22 C21 119.9(2) . . ? C23 C22 C21 122.5(2) . . ? F23 C23 C22 120.9(2) . . ? F23 C23 C24 119.7(2) . . ? C22 C23 C24 119.4(2) . . ? F24 C24 C25 120.0(3) . . ? F24 C24 C23 120.1(3) . . ? C25 C24 C23 119.9(2) . . ? F25 C25 C24 119.9(2) . . ? F25 C25 C26 120.0(2) . . ? C24 C25 C26 120.1(2) . . ? F26 C26 C25 117.6(2) . . ? F26 C26 C21 120.4(2) . . ? C25 C26 C21 122.0(2) . . ? C32 C31 C36 113.0(2) . . ? C32 C31 B1 126.8(2) . . ? C36 C31 B1 120.1(2) . . ? F32 C32 C31 119.9(2) . . ? F32 C32 C33 115.5(2) . . ? C31 C32 C33 124.6(3) . . ? F33 C33 C34 120.0(3) . . ? F33 C33 C32 120.7(3) . . ? C34 C33 C32 119.3(3) . . ? F34 C34 C33 120.4(3) . . ? F34 C34 C35 120.3(3) . . ? C33 C34 C35 119.4(2) . . ? F35 C35 C34 119.5(3) . . ? F35 C35 C36 121.3(3) . . ? C34 C35 C36 119.2(3) . . ? F36 C36 C35 115.9(2) . . ? F36 C36 C31 119.5(2) . . ? C35 C36 C31 124.6(3) . . ? C42 C41 C46 112.6(2) . . ? C42 C41 B1 120.6(2) . . ? C46 C41 B1 126.8(2) . . ? F42 C42 C43 115.1(2) . . ? F42 C42 C41 119.8(2) . . ? C43 C42 C41 125.1(3) . . ? F43 C43 C44 120.0(2) . . ? F43 C43 C42 120.9(3) . . ? C44 C43 C42 119.1(2) . . ? F44 C44 C45 120.6(3) . . ? F44 C44 C43 120.4(3) . . ? C45 C44 C43 118.9(2) . . ? F45 C45 C44 119.6(2) . . ? F45 C45 C46 120.4(3) . . ? C44 C45 C46 120.0(2) . . ? F46 C46 C45 115.5(2) . . ? F46 C46 C41 120.3(2) . . ? C45 C46 C41 124.2(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 P1 C1 C3 -178.63(18) . . . . ? C11 P1 C1 C3 64.7(2) . . . . ? C21 P1 C1 C3 -52.9(2) . . . . ? C4 P1 C1 C2 -52.30(18) . . . . ? C11 P1 C1 C2 -168.99(15) . . . . ? C21 P1 C1 C2 73.38(17) . . . . ? C3 C1 C2 B1 -162.0(2) . . . . ? P1 C1 C2 B1 72.6(2) . . . . ? C5 B1 C2 C1 -48.3(3) . . . . ? C31 B1 C2 C1 73.6(2) . . . . ? C41 B1 C2 C1 -166.3(2) . . . . ? C1 P1 C4 C5 11.2(2) . . . . ? C11 P1 C4 C5 135.07(19) . . . . ? C21 P1 C4 C5 -109.2(2) . . . . ? C1 P1 C4 C6 -158.63(18) . . . . ? C11 P1 C4 C6 -34.8(2) . . . . ? C21 P1 C4 C6 81.0(2) . . . . ? C6 C4 C5 B1 -175.5(2) . . . . ? P1 C4 C5 B1 15.3(3) . . . . ? C2 B1 C5 C4 0.2(4) . . . . ? C31 B1 C5 C4 -118.2(3) . . . . ? C41 B1 C5 C4 125.4(3) . . . . ? C5 C4 C6 C7 112.2(3) . . . . ? P1 C4 C6 C7 -78.6(3) . . . . ? C5 C4 C6 C8 -65.5(3) . . . . ? P1 C4 C6 C8 103.6(2) . . . . ? C4 P1 C11 C12 -90.5(2) . . . . ? C1 P1 C11 C12 27.5(3) . . . . ? C21 P1 C11 C12 146.4(2) . . . . ? C4 P1 C11 C16 79.0(2) . . . . ? C1 P1 C11 C16 -163.0(2) . . . . ? C21 P1 C11 C16 -44.0(2) . . . . ? C16 C11 C12 F12 -179.4(2) . . . . ? P1 C11 C12 F12 -9.5(4) . . . . ? C16 C11 C12 C13 -0.6(4) . . . . ? P1 C11 C12 C13 169.4(2) . . . . ? F12 C12 C13 F13 -1.6(4) . . . . ? C11 C12 C13 F13 179.5(2) . . . . ? F12 C12 C13 C14 177.6(2) . . . . ? C11 C12 C13 C14 -1.2(4) . . . . ? F13 C13 C14 F14 1.3(4) . . . . ? C12 C13 C14 F14 -177.9(2) . . . . ? F13 C13 C14 C15 -179.2(2) . . . . ? C12 C13 C14 C15 1.6(4) . . . . ? F14 C14 C15 F15 -0.9(4) . . . . ? C13 C14 C15 F15 179.6(2) . . . . ? F14 C14 C15 C16 179.4(2) . . . . ? C13 C14 C15 C16 -0.1(4) . . . . ? F15 C15 C16 F16 -1.1(4) . . . . ? C14 C15 C16 F16 178.6(2) . . . . ? F15 C15 C16 C11 178.5(2) . . . . ? C14 C15 C16 C11 -1.8(4) . . . . ? C12 C11 C16 F16 -178.3(2) . . . . ? P1 C11 C16 F16 11.4(3) . . . . ? C12 C11 C16 C15 2.1(4) . . . . ? P1 C11 C16 C15 -168.1(2) . . . . ? C4 P1 C21 C26 23.3(3) . . . . ? C1 P1 C21 C26 -96.9(2) . . . . ? C11 P1 C21 C26 138.7(2) . . . . ? C4 P1 C21 C22 -157.36(19) . . . . ? C1 P1 C21 C22 82.4(2) . . . . ? C11 P1 C21 C22 -41.9(2) . . . . ? C26 C21 C22 F22 179.5(2) . . . . ? P1 C21 C22 F22 0.2(3) . . . . ? C26 C21 C22 C23 -0.7(4) . . . . ? P1 C21 C22 C23 179.9(2) . . . . ? F22 C22 C23 F23 -1.0(4) . . . . ? C21 C22 C23 F23 179.2(2) . . . . ? F22 C22 C23 C24 179.4(2) . . . . ? C21 C22 C23 C24 -0.3(4) . . . . ? F23 C23 C24 F24 0.5(4) . . . . ? C22 C23 C24 F24 -180.0(2) . . . . ? F23 C23 C24 C25 -178.2(2) . . . . ? C22 C23 C24 C25 1.4(4) . . . . ? F24 C24 C25 F25 -0.9(4) . . . . ? C23 C24 C25 F25 177.7(2) . . . . ? F24 C24 C25 C26 180.0(2) . . . . ? C23 C24 C25 C26 -1.4(4) . . . . ? F25 C25 C26 F26 1.5(4) . . . . ? C24 C25 C26 F26 -179.3(2) . . . . ? F25 C25 C26 C21 -178.8(2) . . . . ? C24 C25 C26 C21 0.3(4) . . . . ? C22 C21 C26 F26 -179.6(2) . . . . ? P1 C21 C26 F26 -0.3(3) . . . . ? C22 C21 C26 C25 0.7(4) . . . . ? P1 C21 C26 C25 -179.9(2) . . . . ? C5 B1 C31 C32 8.3(3) . . . . ? C2 B1 C31 C32 -111.3(3) . . . . ? C41 B1 C31 C32 123.1(3) . . . . ? C5 B1 C31 C36 -175.5(2) . . . . ? C2 B1 C31 C36 64.9(3) . . . . ? C41 B1 C31 C36 -60.7(3) . . . . ? C36 C31 C32 F32 178.8(2) . . . . ? B1 C31 C32 F32 -4.8(4) . . . . ? C36 C31 C32 C33 -2.0(4) . . . . ? B1 C31 C32 C33 174.4(2) . . . . ? F32 C32 C33 F33 1.0(4) . . . . ? C31 C32 C33 F33 -178.3(2) . . . . ? F32 C32 C33 C34 180.0(2) . . . . ? C31 C32 C33 C34 0.7(4) . . . . ? F33 C33 C34 F34 0.9(4) . . . . ? C32 C33 C34 F34 -178.0(2) . . . . ? F33 C33 C34 C35 -179.9(2) . . . . ? C32 C33 C34 C35 1.1(4) . . . . ? F34 C34 C35 F35 -1.6(4) . . . . ? C33 C34 C35 F35 179.3(3) . . . . ? F34 C34 C35 C36 177.7(2) . . . . ? C33 C34 C35 C36 -1.5(4) . . . . ? F35 C35 C36 F36 -0.2(4) . . . . ? C34 C35 C36 F36 -179.5(2) . . . . ? F35 C35 C36 C31 179.3(2) . . . . ? C34 C35 C36 C31 0.0(4) . . . . ? C32 C31 C36 F36 -178.9(2) . . . . ? B1 C31 C36 F36 4.4(3) . . . . ? C32 C31 C36 C35 1.6(4) . . . . ? B1 C31 C36 C35 -175.1(2) . . . . ? C5 B1 C41 C42 54.7(3) . . . . ? C2 B1 C41 C42 175.1(2) . . . . ? C31 B1 C41 C42 -65.1(3) . . . . ? C5 B1 C41 C46 -125.3(3) . . . . ? C2 B1 C41 C46 -5.0(4) . . . . ? C31 B1 C41 C46 114.8(3) . . . . ? C46 C41 C42 F42 -176.1(2) . . . . ? B1 C41 C42 F42 3.8(3) . . . . ? C46 C41 C42 C43 2.7(4) . . . . ? B1 C41 C42 C43 -177.3(2) . . . . ? F42 C42 C43 F43 -2.2(3) . . . . ? C41 C42 C43 F43 178.9(2) . . . . ? F42 C42 C43 C44 176.4(2) . . . . ? C41 C42 C43 C44 -2.5(4) . . . . ? F43 C43 C44 F44 0.6(4) . . . . ? C42 C43 C44 F44 -178.0(2) . . . . ? F43 C43 C44 C45 179.5(2) . . . . ? C42 C43 C44 C45 0.9(4) . . . . ? F44 C44 C45 F45 -1.8(4) . . . . ? C43 C44 C45 F45 179.3(2) . . . . ? F44 C44 C45 C46 179.2(2) . . . . ? C43 C44 C45 C46 0.3(4) . . . . ? F45 C45 C46 F46 1.0(3) . . . . ? C44 C45 C46 F46 -180.0(2) . . . . ? F45 C45 C46 C41 -178.9(2) . . . . ? C44 C45 C46 C41 0.1(4) . . . . ? C42 C41 C46 F46 178.6(2) . . . . ? B1 C41 C46 F46 -1.4(4) . . . . ? C42 C41 C46 C45 -1.5(4) . . . . ? B1 C41 C46 C45 178.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 67.13 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.210 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.046 data_erk5903 _database_code_depnum_ccdc_archive 'CCDC 912780' #TrackingRef 'Revision_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H12 B F20 O P' _chemical_formula_weight 858.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8560(4) _cell_length_b 12.7840(6) _cell_length_c 14.4856(12) _cell_angle_alpha 95.877(4) _cell_angle_beta 96.842(6) _cell_angle_gamma 92.121(3) _cell_volume 1617.74(17) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 5166 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.762 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 2.133 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5967 _exptl_absorpt_correction_T_max 0.9586 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ? _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24788 _diffrn_reflns_av_R_equivalents 0.052 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.90 _diffrn_reflns_theta_max 66.73 _reflns_number_total 5522 _reflns_number_gt 4263 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0272P)^2^+1.6007P] 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 5522 _refine_ls_number_parameters 515 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1079 _refine_ls_wR_factor_gt 0.0936 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 0.26924(8) 0.28789(5) 0.74099(5) 0.03928(17) Uani 1 1 d . . . B1 B 0.5316(4) 0.3070(2) 0.6740(2) 0.0407(7) Uani 1 1 d . . . O1 O 0.5472(2) 0.22626(14) 0.74088(12) 0.0430(4) Uani 1 1 d . . . C1 C 0.3433(3) 0.2849(2) 0.63174(18) 0.0423(6) Uani 1 1 d . . . H1 H 0.3385 0.2083 0.6116 0.051 Uiso 1 1 calc R . . C2 C 0.2535(4) 0.3267(3) 0.54714(19) 0.0536(7) Uani 1 1 d . . . H2A H 0.1464 0.3026 0.5432 0.064 Uiso 1 1 calc R . . H2B H 0.2587 0.4038 0.5564 0.064 Uiso 1 1 calc R . . C3 C 0.3130(4) 0.2910(3) 0.4561(2) 0.0751(11) Uani 1 1 d . . . H3A H 0.4137 0.3234 0.4558 0.113 Uiso 1 1 calc R . . H3B H 0.2449 0.3117 0.4043 0.113 Uiso 1 1 calc R . . H3C H 0.3186 0.2150 0.4497 0.113 Uiso 1 1 calc R . . C4 C 0.4477(3) 0.2361(2) 0.80805(18) 0.0409(6) Uani 1 1 d . . . H4 H 0.4901 0.2883 0.8608 0.049 Uiso 1 1 calc R . . C5 C 0.4074(3) 0.1330(2) 0.84339(19) 0.0444(6) Uani 1 1 d . . . C6 C 0.3727(4) 0.1331(3) 0.9338(2) 0.0602(8) Uani 1 1 d . . . H6 H 0.3831 0.1961 0.9741 0.072 Uiso 1 1 calc R . . C7 C 0.3230(5) 0.0410(3) 0.9652(3) 0.0785(11) Uani 1 1 d . . . H7 H 0.2984 0.0415 1.0266 0.094 Uiso 1 1 calc R . . C8 C 0.3094(5) -0.0511(3) 0.9070(3) 0.0797(11) Uani 1 1 d . . . H8 H 0.2750 -0.1137 0.9283 0.096 Uiso 1 1 calc R . . C9 C 0.3459(4) -0.0524(3) 0.8176(3) 0.0727(10) Uani 1 1 d . . . H9 H 0.3379 -0.1160 0.7782 0.087 Uiso 1 1 calc R . . C10 C 0.3949(4) 0.0401(2) 0.7847(2) 0.0557(8) Uani 1 1 d . . . H10 H 0.4191 0.0394 0.7232 0.067 Uiso 1 1 calc R . . C11 C 0.1035(3) 0.2030(2) 0.74837(19) 0.0445(6) Uani 1 1 d . . . C12 C 0.0403(3) 0.1270(2) 0.6780(2) 0.0512(7) Uani 1 1 d . . . F12 F 0.0887(2) 0.12008(15) 0.59352(13) 0.0677(5) Uani 1 1 d . . . C13 C -0.0747(4) 0.0566(3) 0.6914(3) 0.0628(9) Uani 1 1 d . . . F13 F -0.1302(2) -0.01691(16) 0.62174(17) 0.0887(7) Uani 1 1 d . . . C14 C -0.1313(4) 0.0622(3) 0.7753(3) 0.0719(10) Uani 1 1 d . . . F14 F -0.2425(3) -0.0065(2) 0.78829(19) 0.1083(8) Uani 1 1 d . . . C15 C -0.0738(4) 0.1370(3) 0.8460(3) 0.0703(10) Uani 1 1 d . . . F15 F -0.1291(3) 0.1433(2) 0.92804(17) 0.1092(9) Uani 1 1 d . . . C16 C 0.0430(3) 0.2055(2) 0.8326(2) 0.0546(8) Uani 1 1 d . . . F16 F 0.0996(2) 0.27645(15) 0.90393(12) 0.0670(5) Uani 1 1 d . . . C21 C 0.2160(3) 0.4181(2) 0.78495(18) 0.0400(6) Uani 1 1 d . . . C22 C 0.0960(3) 0.4637(2) 0.73489(18) 0.0436(6) Uani 1 1 d . . . F22 F 0.01662(18) 0.40746(13) 0.66041(11) 0.0571(4) Uani 1 1 d . . . C23 C 0.0539(3) 0.5639(2) 0.7593(2) 0.0480(7) Uani 1 1 d . . . F23 F -0.0619(2) 0.60424(14) 0.70862(12) 0.0625(5) Uani 1 1 d . . . C24 C 0.1300(4) 0.6222(2) 0.8362(2) 0.0535(8) Uani 1 1 d . . . F24 F 0.0889(2) 0.71951(14) 0.86117(15) 0.0787(6) Uani 1 1 d . . . C25 C 0.2465(3) 0.5797(2) 0.8900(2) 0.0520(7) Uani 1 1 d . . . F25 F 0.3198(2) 0.63592(15) 0.96584(13) 0.0737(6) Uani 1 1 d . . . C26 C 0.2866(3) 0.4789(2) 0.86425(19) 0.0448(6) Uani 1 1 d . . . F26 F 0.39771(19) 0.44096(13) 0.92081(11) 0.0575(4) Uani 1 1 d . . . C31 C 0.5840(3) 0.4243(2) 0.73260(18) 0.0431(6) Uani 1 1 d . . . C32 C 0.5223(3) 0.5191(2) 0.7161(2) 0.0507(7) Uani 1 1 d . . . F32 F 0.4114(2) 0.52232(14) 0.64380(14) 0.0691(5) Uani 1 1 d . . . C33 C 0.5642(4) 0.6144(2) 0.7680(3) 0.0634(9) Uani 1 1 d . . . F33 F 0.4950(3) 0.70205(15) 0.74699(19) 0.0972(8) Uani 1 1 d . . . C34 C 0.6771(4) 0.6180(3) 0.8415(3) 0.0684(10) Uani 1 1 d . . . F34 F 0.7222(3) 0.71001(18) 0.89257(17) 0.1050(8) Uani 1 1 d . . . C35 C 0.7457(4) 0.5278(3) 0.8615(2) 0.0620(9) Uani 1 1 d . . . F35 F 0.8590(3) 0.53046(19) 0.93299(13) 0.0885(7) Uani 1 1 d . . . C36 C 0.7009(3) 0.4344(2) 0.8067(2) 0.0501(7) Uani 1 1 d . . . F36 F 0.7801(2) 0.35090(15) 0.82896(13) 0.0685(5) Uani 1 1 d . . . C41 C 0.6356(3) 0.2774(2) 0.59039(18) 0.0413(6) Uani 1 1 d . . . C42 C 0.6449(3) 0.1749(2) 0.5509(2) 0.0506(7) Uani 1 1 d . . . F42 F 0.5671(2) 0.09508(13) 0.58199(13) 0.0681(5) Uani 1 1 d . . . C43 C 0.7263(4) 0.1465(3) 0.4776(2) 0.0581(8) Uani 1 1 d . . . F43 F 0.7259(3) 0.04500(16) 0.44150(15) 0.0850(6) Uani 1 1 d . . . C44 C 0.8057(4) 0.2227(3) 0.4406(2) 0.0587(8) Uani 1 1 d . . . F44 F 0.8868(2) 0.19601(18) 0.36934(14) 0.0840(6) Uani 1 1 d . . . C45 C 0.8012(3) 0.3248(3) 0.4761(2) 0.0513(7) Uani 1 1 d . . . F45 F 0.8790(2) 0.40066(15) 0.44050(12) 0.0677(5) Uani 1 1 d . . . C46 C 0.7172(3) 0.3504(2) 0.54804(18) 0.0442(6) Uani 1 1 d . . . F46 F 0.71459(19) 0.45399(13) 0.57569(11) 0.0562(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0391(4) 0.0415(4) 0.0369(4) 0.0020(3) 0.0060(3) 0.0006(3) B1 0.0428(17) 0.0426(17) 0.0376(16) 0.0067(13) 0.0065(13) 0.0030(13) O1 0.0434(10) 0.0456(10) 0.0425(10) 0.0092(8) 0.0112(8) 0.0057(8) C1 0.0449(15) 0.0439(15) 0.0376(14) 0.0020(12) 0.0056(12) 0.0009(12) C2 0.0541(18) 0.0628(19) 0.0443(16) 0.0087(14) 0.0041(14) 0.0064(15) C3 0.071(2) 0.114(3) 0.0401(17) 0.0099(18) 0.0016(16) 0.016(2) C4 0.0425(15) 0.0434(15) 0.0371(14) 0.0053(12) 0.0052(12) 0.0025(12) C5 0.0442(16) 0.0442(16) 0.0460(15) 0.0091(13) 0.0068(13) 0.0035(12) C6 0.077(2) 0.061(2) 0.0459(17) 0.0120(15) 0.0142(16) 0.0043(17) C7 0.101(3) 0.079(3) 0.062(2) 0.028(2) 0.025(2) -0.004(2) C8 0.094(3) 0.066(2) 0.083(3) 0.033(2) 0.013(2) -0.013(2) C9 0.088(3) 0.050(2) 0.079(3) 0.0080(18) 0.005(2) -0.0056(18) C10 0.065(2) 0.0486(18) 0.0531(18) 0.0070(14) 0.0059(15) 0.0000(15) C11 0.0404(15) 0.0447(16) 0.0491(16) 0.0056(13) 0.0081(12) 0.0015(12) C12 0.0465(17) 0.0505(17) 0.0560(18) 0.0017(14) 0.0072(14) 0.0025(14) F12 0.0681(12) 0.0697(12) 0.0608(11) -0.0160(9) 0.0139(9) -0.0124(9) C13 0.0531(19) 0.0508(18) 0.080(2) -0.0007(17) -0.0007(17) -0.0118(15) F13 0.0802(14) 0.0705(13) 0.1059(16) -0.0107(12) -0.0007(12) -0.0273(11) C14 0.056(2) 0.070(2) 0.092(3) 0.018(2) 0.017(2) -0.0149(17) F14 0.0862(16) 0.1043(18) 0.136(2) 0.0242(16) 0.0258(15) -0.0456(14) C15 0.066(2) 0.077(2) 0.073(2) 0.0142(19) 0.0269(19) -0.0106(18) F15 0.1163(19) 0.128(2) 0.0917(16) 0.0157(15) 0.0588(15) -0.0351(16) C16 0.0529(18) 0.0564(18) 0.0553(18) 0.0048(15) 0.0135(15) -0.0029(14) F16 0.0799(13) 0.0735(12) 0.0484(10) -0.0005(9) 0.0220(9) -0.0111(10) C21 0.0399(15) 0.0432(15) 0.0379(14) 0.0055(12) 0.0090(12) -0.0011(12) C22 0.0409(15) 0.0511(17) 0.0395(15) 0.0044(13) 0.0093(12) 0.0014(13) F22 0.0490(10) 0.0660(11) 0.0521(10) -0.0034(8) -0.0044(8) 0.0097(8) C23 0.0455(16) 0.0532(17) 0.0494(16) 0.0125(14) 0.0148(13) 0.0108(13) F23 0.0604(11) 0.0691(11) 0.0641(11) 0.0198(9) 0.0151(9) 0.0247(9) C24 0.0605(19) 0.0414(16) 0.0615(19) 0.0019(14) 0.0214(16) 0.0055(14) F24 0.0914(15) 0.0462(11) 0.0983(15) -0.0046(10) 0.0178(12) 0.0154(10) C25 0.0541(18) 0.0484(17) 0.0517(17) -0.0074(14) 0.0120(14) -0.0028(14) F25 0.0787(13) 0.0633(12) 0.0699(12) -0.0244(10) -0.0013(10) 0.0014(10) C26 0.0440(16) 0.0488(16) 0.0414(15) 0.0015(13) 0.0078(13) 0.0007(13) F26 0.0569(10) 0.0652(11) 0.0453(9) -0.0074(8) -0.0058(8) 0.0115(8) C31 0.0421(15) 0.0483(16) 0.0409(15) 0.0055(12) 0.0140(12) -0.0026(12) C32 0.0482(17) 0.0489(18) 0.0564(18) 0.0025(14) 0.0152(14) -0.0008(13) F32 0.0623(11) 0.0529(11) 0.0910(14) 0.0175(10) -0.0041(10) 0.0044(9) C33 0.067(2) 0.0435(18) 0.082(2) -0.0026(17) 0.031(2) 0.0026(16) F33 0.1014(17) 0.0457(11) 0.148(2) -0.0009(12) 0.0394(16) 0.0107(11) C34 0.079(2) 0.062(2) 0.063(2) -0.0226(18) 0.033(2) -0.0189(19) F34 0.130(2) 0.0791(15) 0.0978(16) -0.0454(13) 0.0412(15) -0.0348(14) C35 0.064(2) 0.080(2) 0.0384(16) -0.0065(16) 0.0121(15) -0.0215(18) F35 0.0872(15) 0.1176(18) 0.0519(11) -0.0034(11) -0.0039(11) -0.0378(13) C36 0.0472(17) 0.0604(19) 0.0432(16) 0.0053(14) 0.0103(13) -0.0055(14) F36 0.0560(11) 0.0766(13) 0.0697(12) 0.0162(10) -0.0110(9) -0.0008(9) C41 0.0385(14) 0.0470(16) 0.0382(14) 0.0029(12) 0.0054(12) 0.0040(12) C42 0.0509(17) 0.0529(18) 0.0483(16) 0.0020(14) 0.0114(14) -0.0025(14) F42 0.0828(13) 0.0485(10) 0.0751(12) -0.0047(9) 0.0313(10) -0.0058(9) C43 0.066(2) 0.0560(19) 0.0506(18) -0.0114(15) 0.0113(15) 0.0070(16) F43 0.1064(17) 0.0660(13) 0.0821(14) -0.0228(11) 0.0356(12) 0.0050(11) C44 0.0537(19) 0.081(2) 0.0424(16) -0.0010(16) 0.0172(14) 0.0046(17) F44 0.0863(14) 0.1041(16) 0.0654(12) -0.0104(11) 0.0409(11) 0.0068(12) C45 0.0455(17) 0.068(2) 0.0421(15) 0.0075(15) 0.0110(13) -0.0006(14) F45 0.0639(11) 0.0857(13) 0.0599(11) 0.0176(10) 0.0270(9) -0.0025(10) C46 0.0430(15) 0.0506(17) 0.0392(15) 0.0040(12) 0.0062(12) 0.0031(12) F46 0.0655(11) 0.0488(10) 0.0579(10) 0.0072(8) 0.0217(8) -0.0004(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 C1 1.781(3) . ? P1 C11 1.814(3) . ? P1 C21 1.819(3) . ? P1 C4 1.929(3) . ? B1 O1 1.486(3) . ? B1 C41 1.630(4) . ? B1 C31 1.667(4) . ? B1 C1 1.709(4) . ? O1 C4 1.388(3) . ? C1 C2 1.534(4) . ? C1 H1 0.9900 . ? C2 C3 1.512(4) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 H3C 0.9700 . ? C4 C5 1.508(4) . ? C4 H4 0.9900 . ? C5 C6 1.380(4) . ? C5 C10 1.380(4) . ? C6 C7 1.381(5) . ? C6 H6 0.9400 . ? C7 C8 1.369(5) . ? C7 H7 0.9400 . ? C8 C9 1.370(5) . ? C8 H8 0.9400 . ? C9 C10 1.393(4) . ? C9 H9 0.9400 . ? C10 H10 0.9400 . ? C11 C12 1.384(4) . ? C11 C16 1.387(4) . ? C12 F12 1.340(3) . ? C12 C13 1.379(4) . ? C13 F13 1.340(4) . ? C13 C14 1.366(5) . ? C14 F14 1.338(4) . ? C14 C15 1.364(5) . ? C15 F15 1.335(4) . ? C15 C16 1.375(4) . ? C16 F16 1.339(3) . ? C21 C26 1.387(4) . ? C21 C22 1.394(4) . ? C22 F22 1.341(3) . ? C22 C23 1.371(4) . ? C23 F23 1.339(3) . ? C23 C24 1.366(4) . ? C24 F24 1.335(3) . ? C24 C25 1.380(4) . ? C25 F25 1.334(3) . ? C25 C26 1.376(4) . ? C26 F26 1.341(3) . ? C31 C32 1.379(4) . ? C31 C36 1.392(4) . ? C32 F32 1.353(4) . ? C32 C33 1.378(4) . ? C33 F33 1.342(4) . ? C33 C34 1.366(5) . ? C34 F34 1.344(4) . ? C34 C35 1.364(5) . ? C35 F35 1.351(4) . ? C35 C36 1.381(4) . ? C36 F36 1.344(4) . ? C41 C42 1.384(4) . ? C41 C46 1.394(4) . ? C42 F42 1.354(3) . ? C42 C43 1.380(4) . ? C43 F43 1.347(3) . ? C43 C44 1.371(5) . ? C44 F44 1.349(3) . ? C44 C45 1.357(4) . ? C45 F45 1.348(3) . ? C45 C46 1.371(4) . ? C46 F46 1.346(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 P1 C11 118.21(13) . . ? C1 P1 C21 113.42(12) . . ? C11 P1 C21 104.14(12) . . ? C1 P1 C4 95.65(12) . . ? C11 P1 C4 110.14(12) . . ? C21 P1 C4 115.74(12) . . ? O1 B1 C41 109.1(2) . . ? O1 B1 C31 108.3(2) . . ? C41 B1 C31 112.1(2) . . ? O1 B1 C1 99.7(2) . . ? C41 B1 C1 109.6(2) . . ? C31 B1 C1 117.2(2) . . ? C4 O1 B1 113.8(2) . . ? C2 C1 B1 128.9(2) . . ? C2 C1 P1 121.1(2) . . ? B1 C1 P1 98.02(16) . . ? C2 C1 H1 101.4 . . ? B1 C1 H1 101.4 . . ? P1 C1 H1 101.4 . . ? C3 C2 C1 112.8(3) . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? C3 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O1 C4 C5 113.2(2) . . ? O1 C4 P1 102.68(16) . . ? C5 C4 P1 109.79(18) . . ? O1 C4 H4 110.3 . . ? C5 C4 H4 110.3 . . ? P1 C4 H4 110.3 . . ? C6 C5 C10 119.9(3) . . ? C6 C5 C4 119.1(3) . . ? C10 C5 C4 120.8(3) . . ? C5 C6 C7 120.2(3) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C8 C7 C6 120.0(3) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 120.2(3) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C8 C9 C10 120.4(3) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C5 C10 C9 119.3(3) . . ? C5 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C12 C11 C16 116.4(3) . . ? C12 C11 P1 124.4(2) . . ? C16 C11 P1 118.9(2) . . ? F12 C12 C13 117.4(3) . . ? F12 C12 C11 120.7(3) . . ? C13 C12 C11 121.8(3) . . ? F13 C13 C14 120.5(3) . . ? F13 C13 C12 119.7(3) . . ? C14 C13 C12 119.8(3) . . ? F14 C14 C15 120.1(3) . . ? F14 C14 C13 119.7(3) . . ? C15 C14 C13 120.2(3) . . ? F15 C15 C14 120.5(3) . . ? F15 C15 C16 120.0(3) . . ? C14 C15 C16 119.6(3) . . ? F16 C16 C15 118.2(3) . . ? F16 C16 C11 119.5(3) . . ? C15 C16 C11 122.2(3) . . ? C26 C21 C22 115.7(2) . . ? C26 C21 P1 125.8(2) . . ? C22 C21 P1 118.5(2) . . ? F22 C22 C23 118.1(2) . . ? F22 C22 C21 119.2(2) . . ? C23 C22 C21 122.7(3) . . ? F23 C23 C24 120.1(3) . . ? F23 C23 C22 120.4(3) . . ? C24 C23 C22 119.5(3) . . ? F24 C24 C23 120.1(3) . . ? F24 C24 C25 119.8(3) . . ? C23 C24 C25 120.1(3) . . ? F25 C25 C26 120.4(3) . . ? F25 C25 C24 120.3(3) . . ? C26 C25 C24 119.3(3) . . ? F26 C26 C25 116.4(2) . . ? F26 C26 C21 121.0(2) . . ? C25 C26 C21 122.6(3) . . ? C32 C31 C36 112.7(3) . . ? C32 C31 B1 126.6(3) . . ? C36 C31 B1 120.7(3) . . ? F32 C32 C33 115.3(3) . . ? F32 C32 C31 119.4(3) . . ? C33 C32 C31 125.3(3) . . ? F33 C33 C34 120.5(3) . . ? F33 C33 C32 120.6(3) . . ? C34 C33 C32 118.9(3) . . ? F34 C34 C35 120.3(4) . . ? F34 C34 C33 120.3(4) . . ? C35 C34 C33 119.4(3) . . ? F35 C35 C34 120.1(3) . . ? F35 C35 C36 120.3(3) . . ? C34 C35 C36 119.6(3) . . ? F36 C36 C35 115.2(3) . . ? F36 C36 C31 120.7(3) . . ? C35 C36 C31 124.1(3) . . ? C42 C41 C46 113.0(2) . . ? C42 C41 B1 122.2(2) . . ? C46 C41 B1 124.8(2) . . ? F42 C42 C43 115.5(3) . . ? F42 C42 C41 120.2(2) . . ? C43 C42 C41 124.3(3) . . ? F43 C43 C44 120.2(3) . . ? F43 C43 C42 120.5(3) . . ? C44 C43 C42 119.3(3) . . ? F44 C44 C45 120.7(3) . . ? F44 C44 C43 120.0(3) . . ? C45 C44 C43 119.3(3) . . ? F45 C45 C44 120.0(3) . . ? F45 C45 C46 120.3(3) . . ? C44 C45 C46 119.7(3) . . ? F46 C46 C45 115.3(3) . . ? F46 C46 C41 120.4(2) . . ? C45 C46 C41 124.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C41 B1 O1 C4 -171.8(2) . . . . ? C31 B1 O1 C4 65.9(3) . . . . ? C1 B1 O1 C4 -57.0(3) . . . . ? O1 B1 C1 C2 -168.2(3) . . . . ? C41 B1 C1 C2 -53.8(4) . . . . ? C31 B1 C1 C2 75.3(3) . . . . ? O1 B1 C1 P1 50.2(2) . . . . ? C41 B1 C1 P1 164.67(19) . . . . ? C31 B1 C1 P1 -66.2(2) . . . . ? C11 P1 C1 C2 68.0(3) . . . . ? C21 P1 C1 C2 -54.3(3) . . . . ? C4 P1 C1 C2 -175.5(2) . . . . ? C11 P1 C1 B1 -146.38(16) . . . . ? C21 P1 C1 B1 91.32(18) . . . . ? C4 P1 C1 B1 -29.91(18) . . . . ? B1 C1 C2 C3 61.6(4) . . . . ? P1 C1 C2 C3 -164.3(2) . . . . ? B1 O1 C4 C5 151.9(2) . . . . ? B1 O1 C4 P1 33.6(2) . . . . ? C1 P1 C4 O1 2.42(19) . . . . ? C11 P1 C4 O1 125.25(17) . . . . ? C21 P1 C4 O1 -117.00(17) . . . . ? C1 P1 C4 C5 -118.27(19) . . . . ? C11 P1 C4 C5 4.6(2) . . . . ? C21 P1 C4 C5 122.32(19) . . . . ? O1 C4 C5 C6 150.2(3) . . . . ? P1 C4 C5 C6 -95.7(3) . . . . ? O1 C4 C5 C10 -34.2(4) . . . . ? P1 C4 C5 C10 79.9(3) . . . . ? C10 C5 C6 C7 -1.2(5) . . . . ? C4 C5 C6 C7 174.5(3) . . . . ? C5 C6 C7 C8 0.7(6) . . . . ? C6 C7 C8 C9 0.4(6) . . . . ? C7 C8 C9 C10 -1.0(6) . . . . ? C6 C5 C10 C9 0.6(5) . . . . ? C4 C5 C10 C9 -175.0(3) . . . . ? C8 C9 C10 C5 0.5(5) . . . . ? C1 P1 C11 C12 7.7(3) . . . . ? C21 P1 C11 C12 134.6(2) . . . . ? C4 P1 C11 C12 -100.7(3) . . . . ? C1 P1 C11 C16 -179.1(2) . . . . ? C21 P1 C11 C16 -52.2(3) . . . . ? C4 P1 C11 C16 72.5(3) . . . . ? C16 C11 C12 F12 178.4(3) . . . . ? P1 C11 C12 F12 -8.2(4) . . . . ? C16 C11 C12 C13 -1.0(4) . . . . ? P1 C11 C12 C13 172.4(2) . . . . ? F12 C12 C13 F13 1.9(5) . . . . ? C11 C12 C13 F13 -178.7(3) . . . . ? F12 C12 C13 C14 -178.1(3) . . . . ? C11 C12 C13 C14 1.4(5) . . . . ? F13 C13 C14 F14 0.4(5) . . . . ? C12 C13 C14 F14 -179.7(3) . . . . ? F13 C13 C14 C15 179.8(3) . . . . ? C12 C13 C14 C15 -0.3(6) . . . . ? F14 C14 C15 F15 -1.0(6) . . . . ? C13 C14 C15 F15 179.6(4) . . . . ? F14 C14 C15 C16 178.4(3) . . . . ? C13 C14 C15 C16 -1.0(6) . . . . ? F15 C15 C16 F16 0.9(5) . . . . ? C14 C15 C16 F16 -178.5(3) . . . . ? F15 C15 C16 C11 -179.3(3) . . . . ? C14 C15 C16 C11 1.4(6) . . . . ? C12 C11 C16 F16 179.5(3) . . . . ? P1 C11 C16 F16 5.7(4) . . . . ? C12 C11 C16 C15 -0.4(5) . . . . ? P1 C11 C16 C15 -174.1(3) . . . . ? C1 P1 C21 C26 -113.1(2) . . . . ? C11 P1 C21 C26 117.0(2) . . . . ? C4 P1 C21 C26 -4.0(3) . . . . ? C1 P1 C21 C22 65.5(2) . . . . ? C11 P1 C21 C22 -64.3(2) . . . . ? C4 P1 C21 C22 174.6(2) . . . . ? C26 C21 C22 F22 -176.3(2) . . . . ? P1 C21 C22 F22 5.0(3) . . . . ? C26 C21 C22 C23 2.9(4) . . . . ? P1 C21 C22 C23 -175.8(2) . . . . ? F22 C22 C23 F23 -1.1(4) . . . . ? C21 C22 C23 F23 179.8(2) . . . . ? F22 C22 C23 C24 178.3(2) . . . . ? C21 C22 C23 C24 -0.9(4) . . . . ? F23 C23 C24 F24 0.1(4) . . . . ? C22 C23 C24 F24 -179.3(3) . . . . ? F23 C23 C24 C25 178.1(3) . . . . ? C22 C23 C24 C25 -1.2(4) . . . . ? F24 C24 C25 F25 -1.2(4) . . . . ? C23 C24 C25 F25 -179.2(3) . . . . ? F24 C24 C25 C26 179.2(3) . . . . ? C23 C24 C25 C26 1.2(4) . . . . ? F25 C25 C26 F26 2.1(4) . . . . ? C24 C25 C26 F26 -178.2(3) . . . . ? F25 C25 C26 C21 -178.6(3) . . . . ? C24 C25 C26 C21 1.1(4) . . . . ? C22 C21 C26 F26 176.2(2) . . . . ? P1 C21 C26 F26 -5.1(4) . . . . ? C22 C21 C26 C25 -3.0(4) . . . . ? P1 C21 C26 C25 175.6(2) . . . . ? O1 B1 C31 C32 -145.1(3) . . . . ? C41 B1 C31 C32 94.5(3) . . . . ? C1 B1 C31 C32 -33.4(4) . . . . ? O1 B1 C31 C36 34.9(3) . . . . ? C41 B1 C31 C36 -85.5(3) . . . . ? C1 B1 C31 C36 146.6(2) . . . . ? C36 C31 C32 F32 177.4(2) . . . . ? B1 C31 C32 F32 -2.6(4) . . . . ? C36 C31 C32 C33 -2.6(4) . . . . ? B1 C31 C32 C33 177.4(3) . . . . ? F32 C32 C33 F33 1.2(4) . . . . ? C31 C32 C33 F33 -178.9(3) . . . . ? F32 C32 C33 C34 -179.1(3) . . . . ? C31 C32 C33 C34 0.9(5) . . . . ? F33 C33 C34 F34 -1.3(5) . . . . ? C32 C33 C34 F34 179.0(3) . . . . ? F33 C33 C34 C35 180.0(3) . . . . ? C32 C33 C34 C35 0.2(5) . . . . ? F34 C34 C35 F35 0.2(5) . . . . ? C33 C34 C35 F35 179.0(3) . . . . ? F34 C34 C35 C36 -178.2(3) . . . . ? C33 C34 C35 C36 0.6(5) . . . . ? F35 C35 C36 F36 -1.6(4) . . . . ? C34 C35 C36 F36 176.9(3) . . . . ? F35 C35 C36 C31 179.0(3) . . . . ? C34 C35 C36 C31 -2.5(5) . . . . ? C32 C31 C36 F36 -176.0(2) . . . . ? B1 C31 C36 F36 4.0(4) . . . . ? C32 C31 C36 C35 3.3(4) . . . . ? B1 C31 C36 C35 -176.6(3) . . . . ? O1 B1 C41 C42 40.6(4) . . . . ? C31 B1 C41 C42 160.6(3) . . . . ? C1 B1 C41 C42 -67.6(3) . . . . ? O1 B1 C41 C46 -142.7(3) . . . . ? C31 B1 C41 C46 -22.8(4) . . . . ? C1 B1 C41 C46 109.0(3) . . . . ? C46 C41 C42 F42 -177.5(3) . . . . ? B1 C41 C42 F42 -0.5(4) . . . . ? C46 C41 C42 C43 0.2(4) . . . . ? B1 C41 C42 C43 177.2(3) . . . . ? F42 C42 C43 F43 -0.3(4) . . . . ? C41 C42 C43 F43 -178.1(3) . . . . ? F42 C42 C43 C44 178.7(3) . . . . ? C41 C42 C43 C44 0.9(5) . . . . ? F43 C43 C44 F44 -1.6(5) . . . . ? C42 C43 C44 F44 179.4(3) . . . . ? F43 C43 C44 C45 178.1(3) . . . . ? C42 C43 C44 C45 -0.8(5) . . . . ? F44 C44 C45 F45 -0.4(5) . . . . ? C43 C44 C45 F45 179.9(3) . . . . ? F44 C44 C45 C46 179.5(3) . . . . ? C43 C44 C45 C46 -0.2(5) . . . . ? F45 C45 C46 F46 2.6(4) . . . . ? C44 C45 C46 F46 -177.2(3) . . . . ? F45 C45 C46 C41 -178.8(3) . . . . ? C44 C45 C46 C41 1.4(5) . . . . ? C42 C41 C46 F46 177.2(2) . . . . ? B1 C41 C46 F46 0.3(4) . . . . ? C42 C41 C46 C45 -1.3(4) . . . . ? B1 C41 C46 C45 -178.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 66.73 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.202 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.047 data_erk5859 _database_code_depnum_ccdc_archive 'CCDC 912781' #TrackingRef 'Revision_final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H23 B F20 O P' _chemical_formula_weight 1001.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 '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 13.525(2) _cell_length_b 13.909(3) _cell_length_c 14.5825(11) _cell_angle_alpha 111.609(7) _cell_angle_beta 113.015(11) _cell_angle_gamma 94.428(12) _cell_volume 2267.7(6) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 7264 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1002 _exptl_absorpt_coefficient_mu 1.609 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6891 _exptl_absorpt_correction_T_max 0.7391 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ? _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD APEXII' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33792 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 67.00 _reflns_number_total 7795 _reflns_number_gt 6896 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. An unidentified disordered solvent molecule was found in the asymmetrical unit and could not be satisfactorily refined. The program SQUEEZE (A. L. Spek J. Appl. Cryst.,2003, 36, 7-13) was therefore used to remove mathematically the effect of the solvent. ; loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 0.500 270 41 ' ' _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^)+(0.0707P)^2^+0.6218P] 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 7795 _refine_ls_number_parameters 614 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1227 _refine_ls_wR_factor_gt 0.1185 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 0.45746(3) 0.29313(3) 0.19781(3) 0.03900(12) Uani 1 1 d . . . B1 B 0.66792(16) 0.39269(16) 0.26321(16) 0.0405(4) Uani 1 1 d . . . O1 O 0.64703(9) 0.27879(9) 0.24482(10) 0.0439(3) Uani 1 1 d . . . C1 C 0.53927(14) 0.41821(14) 0.22612(14) 0.0407(4) Uani 1 1 d . . . H1 H 0.5386 0.4773 0.2896 0.049 Uiso 1 1 calc R . . C2 C 0.49217(15) 0.43988(16) 0.12133(16) 0.0500(4) Uani 1 1 d . . . H2A H 0.5544 0.4789 0.1195 0.060 Uiso 1 1 calc R . . H2B H 0.4603 0.3708 0.0558 0.060 Uiso 1 1 calc R . . C3 C 0.40478(18) 0.5023(2) 0.1125(2) 0.0660(6) Uani 1 1 d . . . H3A H 0.3362 0.4581 0.0976 0.099 Uiso 1 1 calc R . . H3B H 0.3915 0.5227 0.0526 0.099 Uiso 1 1 calc R . . H3C H 0.4305 0.5661 0.1814 0.099 Uiso 1 1 calc R . . C4 C 0.54768(14) 0.21065(14) 0.15493(14) 0.0433(4) Uani 1 1 d . . . H4 H 0.5447 0.2096 0.0856 0.052 Uiso 1 1 calc R . . C5 C 0.53141(15) 0.10011(14) 0.14638(15) 0.0455(4) Uani 1 1 d . . . H5 H 0.4662 0.0478 0.0888 0.055 Uiso 1 1 calc R . . C6 C 0.60557(16) 0.07299(15) 0.21710(15) 0.0478(4) Uani 1 1 d . . . H6 H 0.6694 0.1274 0.2740 0.057 Uiso 1 1 calc R . . C7 C 0.59848(16) -0.03332(15) 0.21584(15) 0.0485(4) Uani 1 1 d . . . C8 C 0.69478(18) -0.05684(17) 0.27428(18) 0.0591(5) Uani 1 1 d . . . H8 H 0.7624 -0.0036 0.3160 0.071 Uiso 1 1 calc R . . C9 C 0.6926(2) -0.15741(19) 0.2721(2) 0.0701(6) Uani 1 1 d . . . H9 H 0.7586 -0.1722 0.3114 0.084 Uiso 1 1 calc R . . C10 C 0.5942(2) -0.23554(18) 0.2124(2) 0.0734(7) Uani 1 1 d . . . H10 H 0.5925 -0.3040 0.2103 0.088 Uiso 1 1 calc R . . C11 C 0.4975(2) -0.21250(18) 0.1555(2) 0.0717(6) Uani 1 1 d . . . H11 H 0.4299 -0.2656 0.1152 0.086 Uiso 1 1 calc R . . C12 C 0.49905(18) -0.11251(16) 0.15709(18) 0.0572(5) Uani 1 1 d . . . H12 H 0.4326 -0.0980 0.1183 0.069 Uiso 1 1 calc R . . C21 C 0.31206(14) 0.26279(14) 0.10256(15) 0.0445(4) Uani 1 1 d . . . F22 F 0.32429(10) 0.12011(12) -0.03849(10) 0.0751(4) Uani 1 1 d . . . C22 C 0.26437(16) 0.18413(17) -0.00409(16) 0.0532(5) Uani 1 1 d . . . F23 F 0.11197(12) 0.09087(16) -0.18061(11) 0.1017(6) Uani 1 1 d . . . C23 C 0.15535(18) 0.1672(2) -0.07816(17) 0.0661(6) Uani 1 1 d . . . F24 F -0.01200(10) 0.21762(15) -0.11432(13) 0.0940(5) Uani 1 1 d . . . C24 C 0.09189(16) 0.2307(2) -0.0437(2) 0.0668(6) Uani 1 1 d . . . F25 F 0.07457(11) 0.36953(13) 0.09706(14) 0.0866(4) Uani 1 1 d . . . C25 C 0.13607(16) 0.30827(19) 0.0638(2) 0.0602(5) Uani 1 1 d . . . F26 F 0.28679(10) 0.40002(10) 0.23876(11) 0.0666(3) Uani 1 1 d . . . C26 C 0.24456(16) 0.32290(16) 0.13537(17) 0.0507(4) Uani 1 1 d . . . C31 C 0.45349(14) 0.27378(14) 0.31274(14) 0.0424(4) Uani 1 1 d . . . F32 F 0.33418(10) 0.10137(9) 0.18449(10) 0.0610(3) Uani 1 1 d . . . C32 C 0.38965(16) 0.17718(15) 0.28954(16) 0.0504(4) Uani 1 1 d . . . F33 F 0.31433(14) 0.06172(11) 0.34278(13) 0.0852(4) Uani 1 1 d . . . C33 C 0.37838(19) 0.15503(17) 0.36976(19) 0.0593(5) Uani 1 1 d . . . F34 F 0.42345(14) 0.21016(13) 0.55681(12) 0.0829(4) Uani 1 1 d . . . C34 C 0.4334(2) 0.23060(19) 0.47789(19) 0.0602(5) Uani 1 1 d . . . F35 F 0.55324(11) 0.39995(11) 0.60989(9) 0.0669(3) Uani 1 1 d . . . C35 C 0.49882(17) 0.32658(17) 0.50475(15) 0.0519(5) Uani 1 1 d . . . F36 F 0.56899(9) 0.44389(9) 0.45291(9) 0.0533(3) Uani 1 1 d . . . C36 C 0.50720(14) 0.34776(15) 0.42281(15) 0.0448(4) Uani 1 1 d . . . C41 C 0.75692(14) 0.46222(15) 0.39424(15) 0.0445(4) Uani 1 1 d . . . F42 F 0.85851(9) 0.32991(10) 0.38304(11) 0.0644(3) Uani 1 1 d . . . C42 C 0.84427(15) 0.42265(17) 0.44374(16) 0.0505(4) Uani 1 1 d . . . F43 F 1.00191(10) 0.42864(14) 0.59523(12) 0.0866(5) Uani 1 1 d . . . C43 C 0.92146(16) 0.4738(2) 0.55352(19) 0.0637(6) Uani 1 1 d . . . F44 F 0.99062(12) 0.62130(16) 0.72722(11) 0.1030(6) Uani 1 1 d . . . C44 C 0.91628(18) 0.5706(2) 0.62040(17) 0.0708(7) Uani 1 1 d . . . F45 F 0.82677(13) 0.70990(13) 0.64062(12) 0.0926(5) Uani 1 1 d . . . C45 C 0.83420(18) 0.61484(19) 0.57647(18) 0.0655(6) Uani 1 1 d . . . F46 F 0.68021(9) 0.61207(9) 0.43060(10) 0.0604(3) Uani 1 1 d . . . C46 C 0.75786(15) 0.56102(16) 0.46593(16) 0.0512(4) Uani 1 1 d . . . C51 C 0.72850(14) 0.41359(15) 0.19035(15) 0.0445(4) Uani 1 1 d . . . F52 F 0.74821(10) 0.59925(9) 0.27693(10) 0.0606(3) Uani 1 1 d . . . C52 C 0.76645(15) 0.51647(16) 0.20615(16) 0.0490(4) Uani 1 1 d . . . F53 F 0.85633(13) 0.64428(12) 0.17347(14) 0.0839(4) Uani 1 1 d . . . C53 C 0.82282(17) 0.54223(19) 0.15402(18) 0.0585(5) Uani 1 1 d . . . F54 F 0.89736(12) 0.48522(15) 0.02753(13) 0.0885(5) Uani 1 1 d . . . C54 C 0.84389(17) 0.4619(2) 0.08049(18) 0.0632(6) Uani 1 1 d . . . F55 F 0.82790(12) 0.27862(13) -0.01079(12) 0.0824(4) Uani 1 1 d . . . C55 C 0.80905(16) 0.3588(2) 0.06154(17) 0.0582(5) Uani 1 1 d . . . F56 F 0.72376(10) 0.23184(10) 0.09239(11) 0.0647(3) Uani 1 1 d . . . C56 C 0.75335(15) 0.33638(16) 0.11632(16) 0.0498(4) Uani 1 1 d . . . C61 C 0.2154(4) 0.6955(4) 0.2641(3) 0.1233(13) Uani 1 1 d . . . H61 H 0.1767 0.6457 0.1894 0.148 Uiso 1 1 calc R . . C62 C 0.2888(5) 0.7864(5) 0.2941(4) 0.1417(17) Uani 1 1 d . . . H62 H 0.3052 0.7978 0.2414 0.170 Uiso 1 1 calc R . . C63 C 0.3398(4) 0.8633(3) 0.4046(4) 0.1265(14) Uani 1 1 d . . . H63 H 0.3890 0.9282 0.4271 0.152 Uiso 1 1 calc R . . C64 C 0.3160(4) 0.8412(3) 0.4779(3) 0.1099(11) Uani 1 1 d . . . H64 H 0.3475 0.8921 0.5521 0.132 Uiso 1 1 calc R . . C65 C 0.2492(5) 0.7490(5) 0.4461(4) 0.1394(16) Uani 1 1 d . . . H65 H 0.2370 0.7335 0.4989 0.167 Uiso 1 1 calc R . . C66 C 0.1983(4) 0.6768(4) 0.3400(4) 0.1353(15) Uani 1 1 d . . . H66 H 0.1499 0.6121 0.3193 0.162 Uiso 1 1 calc R . . C71 C 0.0274(4) -0.0782(3) -0.0663(5) 0.1342(16) Uani 1 1 d . . . H71 H 0.0461 -0.1325 -0.1131 0.161 Uiso 1 1 calc R . . C72 C 0.0862(3) -0.0390(4) 0.0453(5) 0.1293(16) Uani 1 1 d . . . H72 H 0.1455 -0.0664 0.0764 0.155 Uiso 1 1 calc R . . C73 C 0.0594(4) 0.0381(4) 0.1100(4) 0.1325(15) Uani 1 1 d . . . H73 H 0.1007 0.0658 0.1872 0.159 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 0.0354(2) 0.0441(2) 0.0369(2) 0.01872(18) 0.01479(18) 0.00989(17) B1 0.0371(9) 0.0450(10) 0.0412(10) 0.0213(8) 0.0170(8) 0.0121(8) O1 0.0363(6) 0.0471(6) 0.0458(7) 0.0226(5) 0.0138(5) 0.0112(5) C1 0.0365(8) 0.0457(9) 0.0399(9) 0.0208(7) 0.0151(7) 0.0111(7) C2 0.0421(9) 0.0585(11) 0.0528(11) 0.0339(9) 0.0157(8) 0.0120(8) C3 0.0501(11) 0.0797(15) 0.0884(16) 0.0593(13) 0.0278(11) 0.0231(10) C4 0.0410(9) 0.0494(9) 0.0409(9) 0.0209(8) 0.0182(7) 0.0135(7) C5 0.0461(9) 0.0463(9) 0.0410(9) 0.0148(8) 0.0207(8) 0.0123(8) C6 0.0495(10) 0.0456(10) 0.0447(10) 0.0170(8) 0.0203(8) 0.0125(8) C7 0.0542(11) 0.0468(10) 0.0422(9) 0.0179(8) 0.0208(8) 0.0148(8) C8 0.0556(12) 0.0569(11) 0.0560(12) 0.0261(10) 0.0155(9) 0.0144(9) C9 0.0674(14) 0.0652(13) 0.0734(15) 0.0385(12) 0.0185(12) 0.0243(11) C10 0.0788(16) 0.0526(12) 0.0815(16) 0.0365(12) 0.0222(13) 0.0188(11) C11 0.0648(14) 0.0527(12) 0.0812(16) 0.0298(11) 0.0186(12) 0.0067(10) C12 0.0553(11) 0.0507(11) 0.0597(12) 0.0249(9) 0.0193(10) 0.0152(9) C21 0.0380(9) 0.0500(10) 0.0453(9) 0.0242(8) 0.0157(8) 0.0083(7) F22 0.0578(7) 0.0960(10) 0.0436(6) 0.0089(6) 0.0162(6) 0.0214(7) C22 0.0423(10) 0.0688(12) 0.0440(10) 0.0238(9) 0.0166(8) 0.0110(9) F23 0.0602(8) 0.1463(15) 0.0454(7) 0.0137(8) 0.0037(6) 0.0045(9) C23 0.0465(11) 0.0886(16) 0.0441(11) 0.0257(11) 0.0085(9) 0.0006(11) F24 0.0377(6) 0.1476(14) 0.0857(10) 0.0627(10) 0.0075(6) 0.0161(8) C24 0.0358(10) 0.0981(17) 0.0692(14) 0.0497(13) 0.0151(10) 0.0113(11) F25 0.0536(7) 0.1066(11) 0.1110(12) 0.0529(9) 0.0391(8) 0.0407(8) C25 0.0407(10) 0.0741(13) 0.0778(15) 0.0436(12) 0.0274(10) 0.0194(10) F26 0.0544(7) 0.0643(7) 0.0684(8) 0.0166(6) 0.0260(6) 0.0212(6) C26 0.0421(10) 0.0537(11) 0.0575(11) 0.0273(9) 0.0212(9) 0.0098(8) C31 0.0408(9) 0.0472(9) 0.0440(9) 0.0224(8) 0.0207(8) 0.0147(7) F32 0.0661(7) 0.0504(6) 0.0560(7) 0.0178(5) 0.0254(6) 0.0003(5) C32 0.0548(11) 0.0501(10) 0.0515(11) 0.0249(9) 0.0263(9) 0.0144(9) F33 0.1121(11) 0.0667(8) 0.0960(10) 0.0483(8) 0.0557(9) 0.0093(8) C33 0.0703(13) 0.0566(11) 0.0703(14) 0.0392(11) 0.0387(11) 0.0183(10) F34 0.1142(11) 0.1013(10) 0.0781(9) 0.0642(8) 0.0597(9) 0.0417(9) C34 0.0769(14) 0.0740(14) 0.0631(13) 0.0473(11) 0.0440(11) 0.0351(11) F35 0.0762(8) 0.0832(8) 0.0419(6) 0.0262(6) 0.0274(6) 0.0254(7) C35 0.0564(11) 0.0644(12) 0.0427(10) 0.0265(9) 0.0249(9) 0.0255(9) F36 0.0528(6) 0.0547(6) 0.0452(6) 0.0159(5) 0.0224(5) 0.0049(5) C36 0.0416(9) 0.0513(10) 0.0456(10) 0.0235(8) 0.0207(8) 0.0157(8) C41 0.0351(8) 0.0568(10) 0.0436(9) 0.0259(8) 0.0166(7) 0.0074(7) F42 0.0459(6) 0.0757(8) 0.0736(8) 0.0400(7) 0.0205(6) 0.0242(6) C42 0.0370(9) 0.0674(12) 0.0520(11) 0.0340(10) 0.0174(8) 0.0120(8) F43 0.0452(7) 0.1368(13) 0.0819(9) 0.0734(10) 0.0090(6) 0.0198(7) C43 0.0356(10) 0.1003(18) 0.0578(12) 0.0489(13) 0.0115(9) 0.0090(10) F44 0.0637(8) 0.1546(15) 0.0425(7) 0.0268(8) -0.0003(6) -0.0062(9) C44 0.0446(11) 0.1068(19) 0.0400(11) 0.0271(12) 0.0079(9) -0.0028(12) F45 0.0774(9) 0.0906(10) 0.0581(8) -0.0064(7) 0.0221(7) -0.0004(8) C45 0.0503(12) 0.0759(14) 0.0475(11) 0.0112(11) 0.0187(10) -0.0027(10) F46 0.0514(6) 0.0546(6) 0.0580(7) 0.0136(5) 0.0191(5) 0.0121(5) C46 0.0393(9) 0.0614(11) 0.0466(10) 0.0211(9) 0.0169(8) 0.0068(8) C51 0.0338(8) 0.0585(11) 0.0429(9) 0.0263(8) 0.0145(7) 0.0137(8) F52 0.0670(7) 0.0556(6) 0.0686(7) 0.0325(6) 0.0341(6) 0.0185(5) C52 0.0421(9) 0.0602(11) 0.0498(10) 0.0312(9) 0.0183(8) 0.0157(8) F53 0.0864(9) 0.0900(10) 0.1097(11) 0.0698(9) 0.0527(9) 0.0203(8) C53 0.0485(11) 0.0769(14) 0.0651(13) 0.0479(12) 0.0240(10) 0.0150(10) F54 0.0782(9) 0.1387(13) 0.0949(10) 0.0754(10) 0.0588(8) 0.0329(9) C54 0.0472(11) 0.1029(18) 0.0611(13) 0.0526(13) 0.0286(10) 0.0214(11) F55 0.0765(9) 0.1079(11) 0.0766(9) 0.0321(8) 0.0534(8) 0.0339(8) C55 0.0431(10) 0.0885(15) 0.0477(11) 0.0303(10) 0.0233(9) 0.0231(10) F56 0.0629(7) 0.0607(7) 0.0714(8) 0.0196(6) 0.0397(6) 0.0170(6) C56 0.0376(9) 0.0617(11) 0.0485(10) 0.0247(9) 0.0171(8) 0.0132(8) C61 0.146(4) 0.137(3) 0.088(2) 0.045(2) 0.057(2) 0.039(3) C62 0.170(4) 0.201(5) 0.122(3) 0.120(4) 0.082(3) 0.062(4) C63 0.130(3) 0.110(3) 0.157(4) 0.093(3) 0.046(3) 0.040(2) C64 0.144(3) 0.115(3) 0.090(2) 0.049(2) 0.062(2) 0.063(3) C65 0.161(4) 0.168(4) 0.132(4) 0.075(3) 0.099(3) 0.031(3) C66 0.146(4) 0.139(4) 0.128(4) 0.064(3) 0.067(3) 0.012(3) C71 0.112(3) 0.083(2) 0.173(5) 0.025(3) 0.066(3) -0.005(2) C72 0.082(2) 0.081(2) 0.181(5) 0.053(3) 0.027(3) -0.004(2) C73 0.114(3) 0.114(3) 0.119(3) 0.042(3) 0.021(3) -0.012(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 C1 1.7994(18) . ? P1 C21 1.8108(18) . ? P1 C31 1.8124(18) . ? P1 C4 1.8657(18) . ? B1 O1 1.490(2) . ? B1 C41 1.642(3) . ? B1 C51 1.660(3) . ? B1 C1 1.717(2) . ? O1 C4 1.390(2) . ? C1 C2 1.562(2) . ? C1 H1 0.9900 . ? C2 C3 1.513(3) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 H3C 0.9700 . ? C4 C5 1.488(3) . ? C4 H4 0.9900 . ? C5 C6 1.322(3) . ? C5 H5 0.9400 . ? C6 C7 1.467(3) . ? C6 H6 0.9400 . ? C7 C12 1.390(3) . ? C7 C8 1.390(3) . ? C8 C9 1.385(3) . ? C8 H8 0.9400 . ? C9 C10 1.373(3) . ? C9 H9 0.9400 . ? C10 C11 1.383(3) . ? C10 H10 0.9400 . ? C11 C12 1.381(3) . ? C11 H11 0.9400 . ? C12 H12 0.9400 . ? C21 C22 1.373(3) . ? C21 C26 1.388(3) . ? F22 C22 1.342(2) . ? C22 C23 1.382(3) . ? F23 C23 1.324(3) . ? C23 C24 1.377(4) . ? F24 C24 1.326(2) . ? C24 C25 1.378(3) . ? F25 C25 1.332(3) . ? C25 C26 1.373(3) . ? F26 C26 1.338(2) . ? C31 C36 1.385(3) . ? C31 C32 1.387(3) . ? F32 C32 1.346(2) . ? C32 C33 1.373(3) . ? F33 C33 1.332(2) . ? C33 C34 1.373(3) . ? F34 C34 1.334(2) . ? C34 C35 1.371(3) . ? F35 C35 1.335(2) . ? C35 C36 1.374(3) . ? F36 C36 1.337(2) . ? C41 C46 1.382(3) . ? C41 C42 1.395(3) . ? F42 C42 1.347(2) . ? C42 C43 1.378(3) . ? F43 C43 1.348(3) . ? C43 C44 1.367(4) . ? F44 C44 1.338(2) . ? C44 C45 1.365(4) . ? F45 C45 1.348(3) . ? C45 C46 1.384(3) . ? F46 C46 1.354(2) . ? C51 C52 1.384(3) . ? C51 C56 1.385(3) . ? F52 C52 1.349(2) . ? C52 C53 1.378(3) . ? F53 C53 1.343(3) . ? C53 C54 1.373(3) . ? F54 C54 1.345(2) . ? C54 C55 1.362(3) . ? F55 C55 1.345(3) . ? C55 C56 1.386(3) . ? F56 C56 1.350(2) . ? C61 C66 1.323(6) . ? C61 C62 1.354(6) . ? C61 H61 0.9400 . ? C62 C63 1.401(7) . ? C62 H62 0.9400 . ? C63 C64 1.356(6) . ? C63 H63 0.9400 . ? C64 C65 1.316(6) . ? C64 H64 0.9400 . ? C65 C66 1.338(6) . ? C65 H65 0.9400 . ? C66 H66 0.9400 . ? C71 C72 1.358(7) . ? C71 C73 1.368(7) 2 ? C71 H71 0.9400 . ? C72 C73 1.324(7) . ? C72 H72 0.9400 . ? C73 C71 1.368(7) 2 ? C73 H73 0.9400 . ? 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 P1 C21 113.73(8) . . ? C1 P1 C31 118.47(8) . . ? C21 P1 C31 103.56(8) . . ? C1 P1 C4 95.49(8) . . ? C21 P1 C4 119.89(8) . . ? C31 P1 C4 106.33(8) . . ? O1 B1 C41 105.86(14) . . ? O1 B1 C51 111.92(14) . . ? C41 B1 C51 106.83(14) . . ? O1 B1 C1 104.80(13) . . ? C41 B1 C1 114.98(14) . . ? C51 B1 C1 112.36(13) . . ? C4 O1 B1 115.86(13) . . ? C2 C1 B1 116.24(14) . . ? C2 C1 P1 109.66(12) . . ? B1 C1 P1 99.70(11) . . ? C2 C1 H1 110.2 . . ? B1 C1 H1 110.2 . . ? P1 C1 H1 110.2 . . ? C3 C2 C1 116.31(17) . . ? C3 C2 H2A 108.2 . . ? C1 C2 H2A 108.2 . . ? C3 C2 H2B 108.2 . . ? C1 C2 H2B 108.2 . . ? H2A C2 H2B 107.4 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O1 C4 C5 112.06(14) . . ? O1 C4 P1 95.25(11) . . ? C5 C4 P1 117.87(13) . . ? O1 C4 H4 110.3 . . ? C5 C4 H4 110.3 . . ? P1 C4 H4 110.3 . . ? C6 C5 C4 122.18(17) . . ? C6 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? C5 C6 C7 126.70(18) . . ? C5 C6 H6 116.7 . . ? C7 C6 H6 116.7 . . ? C12 C7 C8 118.36(18) . . ? C12 C7 C6 122.52(18) . . ? C8 C7 C6 119.11(18) . . ? C9 C8 C7 121.0(2) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C10 C9 C8 120.1(2) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 119.4(2) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C12 C11 C10 120.9(2) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C7 120.2(2) . . ? C11 C12 H12 119.9 . . ? C7 C12 H12 119.9 . . ? C22 C21 C26 117.11(17) . . ? C22 C21 P1 123.04(14) . . ? C26 C21 P1 119.80(14) . . ? F22 C22 C21 119.59(16) . . ? F22 C22 C23 118.13(19) . . ? C21 C22 C23 122.3(2) . . ? F23 C23 C24 120.2(2) . . ? F23 C23 C22 120.8(2) . . ? C24 C23 C22 119.0(2) . . ? F24 C24 C23 119.9(2) . . ? F24 C24 C25 119.8(2) . . ? C23 C24 C25 120.29(19) . . ? F25 C25 C26 120.5(2) . . ? F25 C25 C24 120.24(19) . . ? C26 C25 C24 119.3(2) . . ? F26 C26 C25 118.50(19) . . ? F26 C26 C21 119.47(16) . . ? C25 C26 C21 122.0(2) . . ? C36 C31 C32 116.21(16) . . ? C36 C31 P1 125.98(14) . . ? C32 C31 P1 117.79(14) . . ? F32 C32 C33 117.43(17) . . ? F32 C32 C31 119.85(16) . . ? C33 C32 C31 122.71(19) . . ? F33 C33 C32 120.3(2) . . ? F33 C33 C34 120.56(18) . . ? C32 C33 C34 119.12(19) . . ? F34 C34 C35 120.1(2) . . ? F34 C34 C33 119.8(2) . . ? C35 C34 C33 120.09(18) . . ? F35 C35 C34 120.32(17) . . ? F35 C35 C36 119.92(18) . . ? C34 C35 C36 119.76(19) . . ? F36 C36 C35 117.40(17) . . ? F36 C36 C31 120.51(15) . . ? C35 C36 C31 122.09(18) . . ? C46 C41 C42 112.94(17) . . ? C46 C41 B1 127.21(16) . . ? C42 C41 B1 119.85(17) . . ? F42 C42 C43 115.78(18) . . ? F42 C42 C41 120.09(17) . . ? C43 C42 C41 124.1(2) . . ? F43 C43 C44 119.9(2) . . ? F43 C43 C42 120.2(2) . . ? C44 C43 C42 119.9(2) . . ? F44 C44 C45 120.4(3) . . ? F44 C44 C43 120.6(2) . . ? C45 C44 C43 118.94(19) . . ? F45 C45 C44 120.2(2) . . ? F45 C45 C46 120.2(2) . . ? C44 C45 C46 119.6(2) . . ? F46 C46 C41 120.63(16) . . ? F46 C46 C45 114.89(19) . . ? C41 C46 C45 124.5(2) . . ? C52 C51 C56 113.41(17) . . ? C52 C51 B1 120.44(16) . . ? C56 C51 B1 126.01(16) . . ? F52 C52 C53 116.04(18) . . ? F52 C52 C51 119.31(16) . . ? C53 C52 C51 124.7(2) . . ? F53 C53 C54 119.85(18) . . ? F53 C53 C52 121.0(2) . . ? C54 C53 C52 119.2(2) . . ? F54 C54 C55 120.9(2) . . ? F54 C54 C53 120.1(2) . . ? C55 C54 C53 119.06(18) . . ? F55 C55 C54 120.17(19) . . ? F55 C55 C56 119.9(2) . . ? C54 C55 C56 120.0(2) . . ? F56 C56 C51 121.22(17) . . ? F56 C56 C55 115.04(18) . . ? C51 C56 C55 123.74(19) . . ? C66 C61 C62 120.0(4) . . ? C66 C61 H61 120.0 . . ? C62 C61 H61 120.0 . . ? C61 C62 C63 119.3(4) . . ? C61 C62 H62 120.4 . . ? C63 C62 H62 120.4 . . ? C64 C63 C62 118.0(4) . . ? C64 C63 H63 121.0 . . ? C62 C63 H63 121.0 . . ? C65 C64 C63 120.6(4) . . ? C65 C64 H64 119.7 . . ? C63 C64 H64 119.7 . . ? C64 C65 C66 121.3(4) . . ? C64 C65 H65 119.3 . . ? C66 C65 H65 119.3 . . ? C61 C66 C65 120.7(5) . . ? C61 C66 H66 119.6 . . ? C65 C66 H66 119.6 . . ? C72 C71 C73 119.4(4) . 2 ? C72 C71 H71 120.3 . . ? C73 C71 H71 120.3 2 . ? C73 C72 C71 119.5(4) . . ? C73 C72 H72 120.2 . . ? C71 C72 H72 120.2 . . ? C72 C73 C71 121.1(5) . 2 ? C72 C73 H73 119.5 . . ? C71 C73 H73 119.5 2 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C41 B1 O1 C4 157.36(14) . . . . ? C51 B1 O1 C4 -86.62(17) . . . . ? C1 B1 O1 C4 35.41(18) . . . . ? O1 B1 C1 C2 -113.16(16) . . . . ? C41 B1 C1 C2 131.06(16) . . . . ? C51 B1 C1 C2 8.6(2) . . . . ? O1 B1 C1 P1 4.54(14) . . . . ? C41 B1 C1 P1 -111.24(14) . . . . ? C51 B1 C1 P1 126.28(13) . . . . ? C21 P1 C1 C2 -32.69(15) . . . . ? C31 P1 C1 C2 -154.68(12) . . . . ? C4 P1 C1 C2 93.40(13) . . . . ? C21 P1 C1 B1 -155.20(11) . . . . ? C31 P1 C1 B1 82.81(12) . . . . ? C4 P1 C1 B1 -29.11(11) . . . . ? B1 C1 C2 C3 -157.31(17) . . . . ? P1 C1 C2 C3 90.63(18) . . . . ? B1 O1 C4 C5 -177.17(14) . . . . ? B1 O1 C4 P1 -54.23(15) . . . . ? C1 P1 C4 O1 47.69(11) . . . . ? C21 P1 C4 O1 169.12(10) . . . . ? C31 P1 C4 O1 -74.12(12) . . . . ? C1 P1 C4 C5 166.06(14) . . . . ? C21 P1 C4 C5 -72.51(16) . . . . ? C31 P1 C4 C5 44.25(15) . . . . ? O1 C4 C5 C6 -0.7(2) . . . . ? P1 C4 C5 C6 -109.77(18) . . . . ? C4 C5 C6 C7 -179.42(17) . . . . ? C5 C6 C7 C12 -17.7(3) . . . . ? C5 C6 C7 C8 161.5(2) . . . . ? C12 C7 C8 C9 1.6(3) . . . . ? C6 C7 C8 C9 -177.6(2) . . . . ? C7 C8 C9 C10 -0.7(4) . . . . ? C8 C9 C10 C11 -0.4(4) . . . . ? C9 C10 C11 C12 0.6(4) . . . . ? C10 C11 C12 C7 0.3(4) . . . . ? C8 C7 C12 C11 -1.4(3) . . . . ? C6 C7 C12 C11 177.8(2) . . . . ? C1 P1 C21 C22 108.36(17) . . . . ? C31 P1 C21 C22 -121.72(16) . . . . ? C4 P1 C21 C22 -3.5(2) . . . . ? C1 P1 C21 C26 -69.36(17) . . . . ? C31 P1 C21 C26 60.55(16) . . . . ? C4 P1 C21 C26 178.73(14) . . . . ? C26 C21 C22 F22 -176.70(17) . . . . ? P1 C21 C22 F22 5.5(3) . . . . ? C26 C21 C22 C23 2.6(3) . . . . ? P1 C21 C22 C23 -175.19(17) . . . . ? F22 C22 C23 F23 -1.0(3) . . . . ? C21 C22 C23 F23 179.7(2) . . . . ? F22 C22 C23 C24 178.7(2) . . . . ? C21 C22 C23 C24 -0.6(3) . . . . ? F23 C23 C24 F24 -2.1(3) . . . . ? C22 C23 C24 F24 178.2(2) . . . . ? F23 C23 C24 C25 178.3(2) . . . . ? C22 C23 C24 C25 -1.4(3) . . . . ? F24 C24 C25 F25 0.5(3) . . . . ? C23 C24 C25 F25 -179.9(2) . . . . ? F24 C24 C25 C26 -178.4(2) . . . . ? C23 C24 C25 C26 1.3(3) . . . . ? F25 C25 C26 F26 -0.2(3) . . . . ? C24 C25 C26 F26 178.66(19) . . . . ? F25 C25 C26 C21 -177.97(18) . . . . ? C24 C25 C26 C21 0.9(3) . . . . ? C22 C21 C26 F26 179.49(17) . . . . ? P1 C21 C26 F26 -2.7(2) . . . . ? C22 C21 C26 C25 -2.7(3) . . . . ? P1 C21 C26 C25 175.11(16) . . . . ? C1 P1 C31 C36 0.90(19) . . . . ? C21 P1 C31 C36 -126.09(16) . . . . ? C4 P1 C31 C36 106.69(16) . . . . ? C1 P1 C31 C32 179.69(13) . . . . ? C21 P1 C31 C32 52.71(16) . . . . ? C4 P1 C31 C32 -74.51(16) . . . . ? C36 C31 C32 F32 179.52(16) . . . . ? P1 C31 C32 F32 0.6(2) . . . . ? C36 C31 C32 C33 0.6(3) . . . . ? P1 C31 C32 C33 -178.28(16) . . . . ? F32 C32 C33 F33 -0.2(3) . . . . ? C31 C32 C33 F33 178.71(18) . . . . ? F32 C32 C33 C34 -179.75(18) . . . . ? C31 C32 C33 C34 -0.8(3) . . . . ? F33 C33 C34 F34 0.6(3) . . . . ? C32 C33 C34 F34 -179.85(19) . . . . ? F33 C33 C34 C35 -179.77(19) . . . . ? C32 C33 C34 C35 -0.2(3) . . . . ? F34 C34 C35 F35 0.2(3) . . . . ? C33 C34 C35 F35 -179.41(19) . . . . ? F34 C34 C35 C36 -178.94(18) . . . . ? C33 C34 C35 C36 1.4(3) . . . . ? F35 C35 C36 F36 -1.4(3) . . . . ? C34 C35 C36 F36 177.75(17) . . . . ? F35 C35 C36 C31 179.18(16) . . . . ? C34 C35 C36 C31 -1.7(3) . . . . ? C32 C31 C36 F36 -178.77(16) . . . . ? P1 C31 C36 F36 0.0(2) . . . . ? C32 C31 C36 C35 0.6(3) . . . . ? P1 C31 C36 C35 179.44(14) . . . . ? O1 B1 C41 C46 -141.03(18) . . . . ? C51 B1 C41 C46 99.5(2) . . . . ? C1 B1 C41 C46 -25.9(2) . . . . ? O1 B1 C41 C42 39.9(2) . . . . ? C51 B1 C41 C42 -79.51(19) . . . . ? C1 B1 C41 C42 155.08(16) . . . . ? C46 C41 C42 F42 -176.24(16) . . . . ? B1 C41 C42 F42 2.9(3) . . . . ? C46 C41 C42 C43 2.4(3) . . . . ? B1 C41 C42 C43 -178.43(18) . . . . ? F42 C42 C43 F43 -2.8(3) . . . . ? C41 C42 C43 F43 178.53(17) . . . . ? F42 C42 C43 C44 177.34(18) . . . . ? C41 C42 C43 C44 -1.3(3) . . . . ? F43 C43 C44 F44 0.1(3) . . . . ? C42 C43 C44 F44 -179.99(19) . . . . ? F43 C43 C44 C45 179.97(19) . . . . ? C42 C43 C44 C45 -0.2(3) . . . . ? F44 C44 C45 F45 -0.5(3) . . . . ? C43 C44 C45 F45 179.7(2) . . . . ? F44 C44 C45 C46 -179.8(2) . . . . ? C43 C44 C45 C46 0.4(3) . . . . ? C42 C41 C46 F46 178.52(16) . . . . ? B1 C41 C46 F46 -0.6(3) . . . . ? C42 C41 C46 C45 -2.2(3) . . . . ? B1 C41 C46 C45 178.73(18) . . . . ? F45 C45 C46 F46 1.0(3) . . . . ? C44 C45 C46 F46 -179.75(19) . . . . ? F45 C45 C46 C41 -178.40(19) . . . . ? C44 C45 C46 C41 0.9(3) . . . . ? O1 B1 C51 C52 -172.37(15) . . . . ? C41 B1 C51 C52 -56.9(2) . . . . ? C1 B1 C51 C52 70.0(2) . . . . ? O1 B1 C51 C56 3.0(2) . . . . ? C41 B1 C51 C56 118.43(18) . . . . ? C1 B1 C51 C56 -114.59(19) . . . . ? C56 C51 C52 F52 -179.58(15) . . . . ? B1 C51 C52 F52 -3.7(2) . . . . ? C56 C51 C52 C53 0.5(3) . . . . ? B1 C51 C52 C53 176.42(17) . . . . ? F52 C52 C53 F53 -0.3(3) . . . . ? C51 C52 C53 F53 179.60(17) . . . . ? F52 C52 C53 C54 -179.74(17) . . . . ? C51 C52 C53 C54 0.2(3) . . . . ? F53 C53 C54 F54 -0.4(3) . . . . ? C52 C53 C54 F54 179.01(18) . . . . ? F53 C53 C54 C55 -179.82(18) . . . . ? C52 C53 C54 C55 -0.4(3) . . . . ? F54 C54 C55 F55 0.1(3) . . . . ? C53 C54 C55 F55 179.45(18) . . . . ? F54 C54 C55 C56 -179.50(18) . . . . ? C53 C54 C55 C56 -0.1(3) . . . . ? C52 C51 C56 F56 179.09(16) . . . . ? B1 C51 C56 F56 3.4(3) . . . . ? C52 C51 C56 C55 -1.0(3) . . . . ? B1 C51 C56 C55 -176.67(17) . . . . ? F55 C55 C56 F56 1.2(3) . . . . ? C54 C55 C56 F56 -179.24(17) . . . . ? F55 C55 C56 C51 -178.68(17) . . . . ? C54 C55 C56 C51 0.9(3) . . . . ? C66 C61 C62 C63 -4.6(8) . . . . ? C61 C62 C63 C64 2.3(7) . . . . ? C62 C63 C64 C65 1.7(7) . . . . ? C63 C64 C65 C66 -3.5(8) . . . . ? C62 C61 C66 C65 2.9(8) . . . . ? C64 C65 C66 C61 1.2(9) . . . . ? C73 C71 C72 C73 -0.7(7) 2 . . . ? C71 C72 C73 C71 0.7(7) . . . 2 ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.206 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.042 #============================================================================= # end of cif data for "erk5859" (compound trans-8) #============================================================================= #============================================================================= # end of cif file #=============================================================================