# 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_erk7186 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H33 P' _chemical_formula_weight 364.48 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' 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 Cc 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' _cell_length_a 16.95660(10) _cell_length_b 9.47770(10) _cell_length_c 15.61850(10) _cell_angle_alpha 90.00 _cell_angle_beta 108.3410(10) _cell_angle_gamma 90.00 _cell_volume 2382.53(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 1956 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.016 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 1.032 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8861 _exptl_absorpt_correction_T_max 0.9796 _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 6371 _diffrn_reflns_av_R_equivalents 0.047 _diffrn_reflns_av_sigmaI/netI 0.0549 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 5.42 _diffrn_reflns_theta_max 66.76 _reflns_number_total 3532 _reflns_number_gt 2848 _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^)+(0.0489P)^2^+2.4542P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.48(4) _refine_ls_number_reflns 3532 _refine_ls_number_parameters 244 _refine_ls_number_restraints 32 _refine_ls_R_factor_all 0.0759 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1424 _refine_ls_wR_factor_gt 0.1289 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.060 _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 0.08335(6) 0.96864(11) 0.06307(7) 0.0501(3) Uani 1 1 d . . . C1 C 0.1035(3) 0.7898(5) 0.0962(3) 0.0577(11) Uani 1 1 d . . . C2 C 0.1101(3) 0.6638(5) 0.1015(4) 0.0641(12) Uani 1 1 d . . . C3 C 0.1185(3) 0.5127(6) 0.1091(5) 0.0837(16) Uani 1 1 d . . . C4 C 0.1354(4) 0.4396(7) 0.0391(5) 0.111(2) Uani 1 1 d U . . H4A H 0.1415 0.3410 0.0421 0.133 Uiso 1 1 calc R . . H4B H 0.1407 0.4891 -0.0110 0.133 Uiso 1 1 calc R . . C5 C 0.1091(5) 0.4489(7) 0.1887(6) 0.120(2) Uani 1 1 d U . . H5A H 0.1204 0.3486 0.1884 0.180 Uiso 1 1 calc R . . H5B H 0.0527 0.4631 0.1897 0.180 Uiso 1 1 calc R . . H5C H 0.1478 0.4918 0.2417 0.180 Uiso 1 1 calc R . . C6 C 0.1845(3) 1.0434(5) 0.1053(3) 0.0520(10) Uani 1 1 d . . . C7 C 0.2494(3) 1.1084(5) 0.1184(3) 0.0571(11) Uani 1 1 d . . . C8 C 0.3266(3) 1.1835(6) 0.1355(4) 0.0696(13) Uani 1 1 d . . . C9 C 0.3420(4) 1.3012(7) 0.1917(4) 0.0979(19) Uani 1 1 d U . . H9A H 0.3909 1.3539 0.2005 0.117 Uiso 1 1 calc R . . H9B H 0.3036 1.3279 0.2209 0.117 Uiso 1 1 calc R . . C10 C 0.3826(4) 1.1378(9) 0.0894(5) 0.123(3) Uani 1 1 d U . . H10A H 0.3541 1.1369 0.0250 0.184 Uiso 1 1 calc R . . H10B H 0.4022 1.0436 0.1094 0.184 Uiso 1 1 calc R . . H10C H 0.4295 1.2020 0.1027 0.184 Uiso 1 1 calc R . . C11 C 0.0297(2) 1.0418(4) 0.1398(3) 0.0504(9) Uani 1 1 d . . . C12 C 0.0623(3) 1.0358(5) 0.2354(3) 0.0553(10) Uani 1 1 d . . . C13 C 0.0189(3) 1.1066(6) 0.2852(4) 0.0713(14) Uani 1 1 d . . . H13 H 0.0401 1.1030 0.3484 0.086 Uiso 1 1 calc R . . C14 C -0.0537(3) 1.1819(6) 0.2463(4) 0.0814(16) Uani 1 1 d . . . C15 C -0.0848(3) 1.1821(5) 0.1527(4) 0.0771(15) Uani 1 1 d . . . H15 H -0.1344 1.2313 0.1248 0.093 Uiso 1 1 calc R . . C16 C -0.0463(3) 1.1131(5) 0.0983(3) 0.0598(11) Uani 1 1 d . . . C17 C 0.1401(3) 0.9564(5) 0.2871(3) 0.0591(11) Uani 1 1 d . . . H17 H 0.1653 0.9182 0.2427 0.071 Uiso 1 1 calc R . . C18 C 0.1181(4) 0.8307(7) 0.3376(4) 0.0850(16) Uani 1 1 d . . . H18A H 0.0938 0.8652 0.3821 0.127 Uiso 1 1 calc R . . H18B H 0.1680 0.7775 0.3675 0.127 Uiso 1 1 calc R . . H18C H 0.0785 0.7702 0.2950 0.127 Uiso 1 1 calc R . . C19 C 0.2044(3) 1.0537(7) 0.3514(3) 0.0871(17) Uani 1 1 d . . . H19A H 0.2158 1.1330 0.3179 0.131 Uiso 1 1 calc R . . H19B H 0.2553 1.0015 0.3790 0.131 Uiso 1 1 calc R . . H19C H 0.1827 1.0880 0.3980 0.131 Uiso 1 1 calc R . . C20 C -0.0985(5) 1.2612(9) 0.3024(6) 0.126(3) Uani 1 1 d U . . H20 H -0.0699 1.2066 0.3574 0.151 Uiso 1 1 calc R . . C21 C -0.0567(5) 1.3891(8) 0.3398(6) 0.135(3) Uani 1 1 d . . . H21A H -0.0462 1.4446 0.2924 0.202 Uiso 1 1 calc R . . H21B H -0.0044 1.3665 0.3853 0.202 Uiso 1 1 calc R . . H21C H -0.0913 1.4427 0.3672 0.202 Uiso 1 1 calc R . . C22 C -0.1747(6) 1.2089(13) 0.2990(8) 0.188(5) Uani 1 1 d . . . H22A H -0.2163 1.2427 0.2448 0.281 Uiso 1 1 calc R . . H22B H -0.1886 1.2402 0.3515 0.281 Uiso 1 1 calc R . . H22C H -0.1731 1.1066 0.2981 0.281 Uiso 1 1 calc R . . C23 C -0.0875(3) 1.1188(6) -0.0051(4) 0.0785(16) Uani 1 1 d . . . H23 H -0.0598 1.0479 -0.0324 0.094 Uiso 1 1 calc R . . C24 C -0.1800(4) 1.0814(9) -0.0324(5) 0.129(3) Uani 1 1 d . . . H24A H -0.2097 1.1550 -0.0121 0.194 Uiso 1 1 calc R . . H24B H -0.1869 0.9924 -0.0048 0.194 Uiso 1 1 calc R . . H24C H -0.2021 1.0730 -0.0975 0.194 Uiso 1 1 calc R . . C25 C -0.0751(5) 1.2636(8) -0.0421(5) 0.123(3) Uani 1 1 d . . . H25A H -0.0985 1.2631 -0.1073 0.185 Uiso 1 1 calc R . . H25B H -0.0162 1.2847 -0.0250 0.185 Uiso 1 1 calc R . . H25C H -0.1029 1.3349 -0.0173 0.185 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 0.0584(5) 0.0455(5) 0.0471(5) -0.0036(6) 0.0175(4) -0.0053(6) C1 0.056(2) 0.054(3) 0.066(3) -0.008(2) 0.023(2) -0.005(2) C2 0.052(2) 0.042(3) 0.096(3) -0.001(2) 0.021(2) -0.0042(19) C3 0.061(3) 0.055(3) 0.125(5) 0.001(3) 0.015(3) -0.006(2) C4 0.111(4) 0.064(4) 0.148(5) -0.016(4) 0.028(4) 0.020(3) C5 0.122(5) 0.085(4) 0.149(6) 0.026(4) 0.039(4) -0.008(4) C6 0.066(3) 0.046(2) 0.051(2) 0.004(2) 0.027(2) 0.003(2) C7 0.065(3) 0.048(3) 0.062(3) 0.006(2) 0.027(2) -0.003(2) C8 0.057(3) 0.069(3) 0.085(3) 0.012(3) 0.025(3) -0.010(2) C9 0.092(4) 0.092(4) 0.106(4) -0.012(4) 0.026(3) -0.032(3) C10 0.098(4) 0.140(6) 0.150(6) -0.017(5) 0.069(4) -0.026(4) C11 0.052(2) 0.044(2) 0.056(2) -0.002(2) 0.0165(18) -0.0070(18) C12 0.056(2) 0.057(3) 0.057(3) -0.008(2) 0.024(2) -0.017(2) C13 0.070(3) 0.082(4) 0.077(3) -0.026(3) 0.044(3) -0.019(3) C14 0.071(3) 0.077(4) 0.111(5) -0.039(3) 0.049(3) -0.018(3) C15 0.057(3) 0.055(3) 0.124(5) -0.013(3) 0.035(3) 0.007(2) C16 0.056(3) 0.047(2) 0.072(3) -0.001(2) 0.013(2) -0.003(2) C17 0.058(3) 0.074(3) 0.046(2) -0.004(2) 0.019(2) -0.010(2) C18 0.097(4) 0.090(4) 0.075(3) 0.013(3) 0.038(3) -0.005(3) C19 0.073(3) 0.114(5) 0.064(3) -0.013(3) 0.006(3) -0.014(3) C20 0.108(4) 0.123(5) 0.176(6) -0.063(5) 0.088(4) -0.015(4) C21 0.174(7) 0.109(6) 0.154(7) -0.062(5) 0.098(6) -0.010(5) C22 0.126(7) 0.246(14) 0.241(12) -0.099(10) 0.130(8) -0.046(7) C23 0.062(3) 0.075(4) 0.086(4) 0.005(3) 0.004(3) 0.013(3) C24 0.089(5) 0.138(7) 0.125(6) 0.005(5) -0.017(4) -0.035(4) C25 0.133(6) 0.107(6) 0.108(5) 0.031(4) 0.007(4) -0.020(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C1 1.774(5) . ? P1 C6 1.780(5) . ? P1 C11 1.852(4) . ? C1 C2 1.200(6) . ? C2 C3 1.440(7) . ? C3 C4 1.398(9) . ? C3 C5 1.436(9) . ? C4 H4A 0.9400 . ? C4 H4B 0.9400 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C5 H5C 0.9700 . ? C6 C7 1.220(6) . ? C7 C8 1.440(6) . ? C8 C9 1.393(7) . ? C8 C10 1.427(8) . ? C9 H9A 0.9400 . ? C9 H9B 0.9400 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 H10C 0.9700 . ? C11 C16 1.417(6) . ? C11 C12 1.421(6) . ? C12 C13 1.399(6) . ? C12 C17 1.514(6) . ? C13 C14 1.386(8) . ? C13 H13 0.9400 . ? C14 C15 1.389(8) . ? C14 C20 1.527(8) . ? C15 C16 1.387(7) . ? C15 H15 0.9400 . ? C16 C23 1.545(7) . ? C17 C19 1.535(7) . ? C17 C18 1.538(7) . ? C17 H17 0.9900 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 H18C 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 H19C 0.9700 . ? C20 C22 1.369(10) . ? C20 C21 1.432(10) . ? C20 H20 0.9900 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C21 H21C 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C22 H22C 0.9700 . ? C23 C25 1.529(9) . ? C23 C24 1.532(8) . ? C23 H23 0.9900 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C24 H24C 0.9700 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C25 H25C 0.9700 . ? 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 C6 101.4(2) . . ? C1 P1 C11 104.9(2) . . ? C6 P1 C11 102.91(18) . . ? C2 C1 P1 167.6(4) . . ? C1 C2 C3 179.3(6) . . ? C4 C3 C5 125.0(6) . . ? C4 C3 C2 117.9(6) . . ? C5 C3 C2 117.1(6) . . ? C3 C4 H4A 120.0 . . ? C3 C4 H4B 120.0 . . ? H4A C4 H4B 120.0 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 P1 167.3(4) . . ? C6 C7 C8 178.9(5) . . ? C9 C8 C10 122.5(5) . . ? C9 C8 C7 119.5(5) . . ? C10 C8 C7 117.9(5) . . ? C8 C9 H9A 120.0 . . ? C8 C9 H9B 120.0 . . ? H9A C9 H9B 120.0 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 119.7(4) . . ? C16 C11 P1 116.3(3) . . ? C12 C11 P1 123.9(3) . . ? C13 C12 C11 117.8(4) . . ? C13 C12 C17 117.7(4) . . ? C11 C12 C17 124.5(4) . . ? C14 C13 C12 123.6(5) . . ? C14 C13 H13 118.2 . . ? C12 C13 H13 118.2 . . ? C13 C14 C15 116.9(4) . . ? C13 C14 C20 122.4(6) . . ? C15 C14 C20 120.7(6) . . ? C16 C15 C14 123.2(5) . . ? C16 C15 H15 118.4 . . ? C14 C15 H15 118.4 . . ? C15 C16 C11 118.7(4) . . ? C15 C16 C23 118.5(4) . . ? C11 C16 C23 122.8(4) . . ? C12 C17 C19 111.8(4) . . ? C12 C17 C18 110.3(4) . . ? C19 C17 C18 111.5(4) . . ? C12 C17 H17 107.7 . . ? C19 C17 H17 107.7 . . ? C18 C17 H17 107.7 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C22 C20 C21 131.5(7) . . ? C22 C20 C14 115.7(7) . . ? C21 C20 C14 112.3(6) . . ? C22 C20 H20 92.5 . . ? C21 C20 H20 92.5 . . ? C14 C20 H20 92.5 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C25 C23 C24 110.7(5) . . ? C25 C23 C16 110.8(5) . . ? C24 C23 C16 111.7(5) . . ? C25 C23 H23 107.8 . . ? C24 C23 H23 107.8 . . ? C16 C23 H23 107.8 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? 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 C6 P1 C1 C2 -124.5(18) . . . . ? C11 P1 C1 C2 128.6(18) . . . . ? P1 C1 C2 C3 179(100) . . . . ? C1 C2 C3 C4 -143(43) . . . . ? C1 C2 C3 C5 37(43) . . . . ? C1 P1 C6 C7 138.1(18) . . . . ? C11 P1 C6 C7 -113.5(18) . . . . ? P1 C6 C7 C8 -173(100) . . . . ? C6 C7 C8 C9 -85(28) . . . . ? C6 C7 C8 C10 99(28) . . . . ? C1 P1 C11 C16 -128.4(3) . . . . ? C6 P1 C11 C16 125.8(3) . . . . ? C1 P1 C11 C12 54.7(4) . . . . ? C6 P1 C11 C12 -51.1(4) . . . . ? C16 C11 C12 C13 -2.6(6) . . . . ? P1 C11 C12 C13 174.2(3) . . . . ? C16 C11 C12 C17 176.6(4) . . . . ? P1 C11 C12 C17 -6.6(6) . . . . ? C11 C12 C13 C14 0.0(7) . . . . ? C17 C12 C13 C14 -179.3(5) . . . . ? C12 C13 C14 C15 1.8(8) . . . . ? C12 C13 C14 C20 -178.4(5) . . . . ? C13 C14 C15 C16 -0.9(8) . . . . ? C20 C14 C15 C16 179.3(5) . . . . ? C14 C15 C16 C11 -1.7(7) . . . . ? C14 C15 C16 C23 179.1(5) . . . . ? C12 C11 C16 C15 3.4(6) . . . . ? P1 C11 C16 C15 -173.6(4) . . . . ? C12 C11 C16 C23 -177.3(4) . . . . ? P1 C11 C16 C23 5.6(5) . . . . ? C13 C12 C17 C19 -58.0(5) . . . . ? C11 C12 C17 C19 122.8(5) . . . . ? C13 C12 C17 C18 66.6(6) . . . . ? C11 C12 C17 C18 -112.6(5) . . . . ? C13 C14 C20 C22 -112.8(10) . . . . ? C15 C14 C20 C22 66.9(11) . . . . ? C13 C14 C20 C21 74.9(10) . . . . ? C15 C14 C20 C21 -105.3(8) . . . . ? C15 C16 C23 C25 74.9(6) . . . . ? C11 C16 C23 C25 -104.4(6) . . . . ? C15 C16 C23 C24 -49.0(7) . . . . ? C11 C16 C23 C24 131.7(5) . . . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 66.76 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.180 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.035 _database_code_depnum_ccdc_archive 'CCDC 956696' ####################################################################### # # 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_erk7119 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H22 B F10 P' _chemical_formula_weight 626.27 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/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 15.3216(5) _cell_length_b 9.6881(3) _cell_length_c 19.8939(7) _cell_angle_alpha 90.00 _cell_angle_beta 104.373(2) _cell_angle_gamma 90.00 _cell_volume 2860.57(16) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4923 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_absorpt_coefficient_mu 1.636 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6663 _exptl_absorpt_correction_T_max 0.9374 _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 21519 _diffrn_reflns_av_R_equivalents 0.044 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.59 _diffrn_reflns_theta_max 67.11 _reflns_number_total 5019 _reflns_number_gt 4304 _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 hydrogens at C14 atom 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^)+(0.0603P)^2^+1.1298P] 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 5019 _refine_ls_number_parameters 401 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1182 _refine_ls_wR_factor_gt 0.1115 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 0.24295(3) 0.37907(5) 0.15760(3) 0.04379(15) Uani 1 1 d . . . B1 B 0.26304(14) 0.1675(2) 0.06247(11) 0.0437(5) Uani 1 1 d . . . C2 C 0.27048(12) 0.31189(19) 0.08334(10) 0.0434(4) Uani 1 1 d . . . C3 C 0.30101(13) 0.4337(2) 0.05149(10) 0.0475(4) Uani 1 1 d . . . H3 H 0.3146 0.4261 0.0081 0.057 Uiso 1 1 calc R . . C4 C 0.30939(14) 0.5552(2) 0.08420(11) 0.0517(5) Uani 1 1 d . . . C5 C 0.28682(15) 0.5530(2) 0.15411(12) 0.0545(5) Uani 1 1 d . . . H5A H 0.2414 0.6227 0.1565 0.065 Uiso 1 1 calc R . . H5B H 0.3406 0.5687 0.1919 0.065 Uiso 1 1 calc R . . C6 C 0.33578(19) 0.6902(2) 0.05825(14) 0.0693(6) Uani 1 1 d . . . H6A H 0.3533 0.6754 0.0152 0.104 Uiso 1 1 calc R . . H6B H 0.3860 0.7293 0.0925 0.104 Uiso 1 1 calc R . . H6C H 0.2851 0.7533 0.0502 0.104 Uiso 1 1 calc R . . C11 C 0.12759(15) 0.4055(2) 0.14226(12) 0.0556(5) Uani 1 1 d . . . C12 C 0.05135(14) 0.4399(2) 0.11641(12) 0.0580(5) Uani 1 1 d . . . C13 C -0.04054(15) 0.4761(3) 0.08510(13) 0.0671(6) Uani 1 1 d . . . C14 C -0.0600(2) 0.6091(4) 0.06412(17) 0.0830(9) Uani 1 1 d . . . H14A H -0.119(2) 0.630(3) 0.0397(18) 0.101(10) Uiso 1 1 d . . . H14B H -0.015(3) 0.675(4) 0.072(2) 0.128(15) Uiso 1 1 d . . . C15 C -0.1056(2) 0.3669(4) 0.0774(3) 0.1198(14) Uani 1 1 d . . . H15A H -0.1658 0.4049 0.0616 0.180 Uiso 1 1 calc R . . H15B H -0.0998 0.3214 0.1218 0.180 Uiso 1 1 calc R . . H15C H -0.0952 0.3004 0.0438 0.180 Uiso 1 1 calc R . . C21 C 0.28915(13) 0.2848(2) 0.23704(10) 0.0446(4) Uani 1 1 d . . . C22 C 0.38253(13) 0.2560(2) 0.25111(10) 0.0476(4) Uani 1 1 d . . . C23 C 0.41969(15) 0.1663(2) 0.30508(11) 0.0561(5) Uani 1 1 d . . . H23 H 0.4818 0.1475 0.3148 0.067 Uiso 1 1 calc R . . C24 C 0.36945(17) 0.1037(2) 0.34498(11) 0.0602(6) Uani 1 1 d . . . C25 C 0.27927(16) 0.1392(2) 0.33270(11) 0.0582(5) Uani 1 1 d . . . H25 H 0.2450 0.1007 0.3612 0.070 Uiso 1 1 calc R . . C26 C 0.23723(14) 0.2293(2) 0.28012(11) 0.0522(5) Uani 1 1 d . . . C27 C 0.44621(14) 0.3157(3) 0.21195(12) 0.0593(5) Uani 1 1 d . . . H27A H 0.4876 0.3788 0.2418 0.089 Uiso 1 1 calc R . . H27B H 0.4121 0.3652 0.1715 0.089 Uiso 1 1 calc R . . H27C H 0.4799 0.2418 0.1973 0.089 Uiso 1 1 calc R . . C28 C 0.4122(2) 0.0007(3) 0.40041(14) 0.0872(9) Uani 1 1 d . . . H28A H 0.4638 -0.0416 0.3886 0.131 Uiso 1 1 calc R . . H28B H 0.3686 -0.0701 0.4035 0.131 Uiso 1 1 calc R . . H28C H 0.4316 0.0475 0.4447 0.131 Uiso 1 1 calc R . . C29 C 0.13897(16) 0.2603(3) 0.27406(14) 0.0745(7) Uani 1 1 d . . . H29A H 0.1028 0.2209 0.2314 0.112 Uiso 1 1 calc R . . H29B H 0.1301 0.3595 0.2736 0.112 Uiso 1 1 calc R . . H29C H 0.1210 0.2205 0.3133 0.112 Uiso 1 1 calc R . . C31 C 0.29708(13) 0.10985(19) -0.00158(10) 0.0451(4) Uani 1 1 d . . . F32 F 0.44096(8) 0.21335(14) 0.03488(7) 0.0641(3) Uani 1 1 d . . . C32 C 0.38209(14) 0.1343(2) -0.01105(10) 0.0483(5) Uani 1 1 d . . . F33 F 0.49746(10) 0.10389(15) -0.07000(8) 0.0751(4) Uani 1 1 d . . . C33 C 0.41345(15) 0.0783(2) -0.06438(12) 0.0559(5) Uani 1 1 d . . . F34 F 0.38778(13) -0.06120(17) -0.16406(8) 0.0890(5) Uani 1 1 d . . . C34 C 0.35842(19) -0.0053(2) -0.11205(12) 0.0632(6) Uani 1 1 d . . . F35 F 0.21775(14) -0.1130(2) -0.15275(9) 0.1091(6) Uani 1 1 d . . . C35 C 0.27283(19) -0.0321(3) -0.10579(12) 0.0693(7) Uani 1 1 d . . . F36 F 0.16043(10) -0.00733(17) -0.04677(8) 0.0828(5) Uani 1 1 d . . . C36 C 0.24437(15) 0.0239(2) -0.05127(12) 0.0571(5) Uani 1 1 d . . . C41 C 0.22271(13) 0.05900(19) 0.10711(10) 0.0445(4) Uani 1 1 d . . . F42 F 0.36852(8) -0.01816(13) 0.16280(7) 0.0601(3) Uani 1 1 d . . . C42 C 0.27895(14) -0.02230(19) 0.15707(11) 0.0482(5) Uani 1 1 d . . . F43 F 0.30730(11) -0.17919(14) 0.25111(7) 0.0762(4) Uani 1 1 d . . . C43 C 0.24917(17) -0.1061(2) 0.20217(11) 0.0570(5) Uani 1 1 d . . . F44 F 0.12749(13) -0.19636(19) 0.24073(10) 0.1039(6) Uani 1 1 d . . . C44 C 0.15870(19) -0.1150(2) 0.19731(14) 0.0683(6) Uani 1 1 d . . . F45 F 0.01071(10) -0.0468(2) 0.14358(11) 0.1021(6) Uani 1 1 d . . . C45 C 0.09936(16) -0.0394(3) 0.14783(15) 0.0670(6) Uani 1 1 d . . . F46 F 0.07111(8) 0.11861(14) 0.05682(8) 0.0699(4) Uani 1 1 d . . . C46 C 0.13175(14) 0.0458(2) 0.10421(12) 0.0536(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0452(3) 0.0428(3) 0.0425(3) -0.0023(2) 0.0093(2) 0.00122(19) B1 0.0416(11) 0.0444(11) 0.0405(11) 0.0003(9) 0.0015(9) 0.0003(9) C2 0.0452(9) 0.0425(10) 0.0401(10) 0.0011(8) 0.0059(8) -0.0003(8) C3 0.0531(11) 0.0460(11) 0.0435(10) 0.0026(8) 0.0124(8) -0.0007(8) C4 0.0580(11) 0.0426(11) 0.0526(12) 0.0016(9) 0.0105(9) -0.0030(9) C5 0.0635(12) 0.0430(11) 0.0560(12) -0.0072(9) 0.0134(10) -0.0020(9) C6 0.0927(17) 0.0458(12) 0.0704(16) 0.0013(11) 0.0221(13) -0.0121(12) C11 0.0563(12) 0.0595(12) 0.0515(12) -0.0002(10) 0.0143(10) 0.0059(10) C12 0.0524(12) 0.0686(14) 0.0525(12) 0.0019(10) 0.0122(10) 0.0077(10) C13 0.0522(12) 0.0892(18) 0.0587(14) 0.0015(13) 0.0114(10) 0.0127(12) C14 0.0716(18) 0.096(2) 0.0765(19) 0.0084(16) 0.0089(15) 0.0290(17) C15 0.0582(17) 0.125(3) 0.162(4) 0.015(3) 0.001(2) -0.0042(18) C21 0.0501(10) 0.0450(10) 0.0387(10) -0.0053(8) 0.0107(8) 0.0001(8) C22 0.0479(10) 0.0517(11) 0.0412(10) -0.0094(9) 0.0072(8) 0.0005(8) C23 0.0572(12) 0.0650(13) 0.0424(11) -0.0056(10) 0.0054(9) 0.0123(10) C24 0.0795(15) 0.0600(13) 0.0414(11) -0.0026(10) 0.0152(11) 0.0161(11) C25 0.0746(14) 0.0608(13) 0.0435(11) 0.0019(10) 0.0228(10) 0.0050(11) C26 0.0577(11) 0.0562(12) 0.0453(11) -0.0032(9) 0.0174(9) 0.0023(9) C27 0.0452(11) 0.0744(15) 0.0567(13) -0.0006(11) 0.0096(9) -0.0024(10) C28 0.114(2) 0.096(2) 0.0558(15) 0.0201(14) 0.0281(15) 0.0432(17) C29 0.0611(13) 0.102(2) 0.0669(15) 0.0183(14) 0.0293(12) 0.0080(13) C31 0.0537(11) 0.0376(9) 0.0406(10) 0.0006(8) 0.0052(8) 0.0002(8) F32 0.0539(7) 0.0712(8) 0.0662(8) -0.0162(6) 0.0130(6) -0.0109(6) C32 0.0570(11) 0.0419(10) 0.0440(11) 0.0004(8) 0.0091(9) 0.0010(8) F33 0.0737(9) 0.0811(9) 0.0803(10) 0.0072(7) 0.0376(7) 0.0084(7) C33 0.0674(13) 0.0489(11) 0.0538(12) 0.0092(10) 0.0197(10) 0.0092(10) F34 0.1370(14) 0.0798(10) 0.0601(9) -0.0115(7) 0.0430(9) 0.0138(9) C34 0.0929(17) 0.0529(12) 0.0471(12) -0.0018(10) 0.0237(12) 0.0080(12) F35 0.1299(15) 0.1150(14) 0.0787(11) -0.0560(10) 0.0188(10) -0.0363(11) C35 0.0965(19) 0.0586(14) 0.0472(12) -0.0170(11) 0.0075(12) -0.0074(13) F36 0.0690(9) 0.0991(11) 0.0771(10) -0.0318(8) 0.0119(7) -0.0285(8) C36 0.0630(13) 0.0542(12) 0.0513(12) -0.0074(10) 0.0089(10) -0.0091(10) C41 0.0506(10) 0.0375(9) 0.0430(10) -0.0045(8) 0.0074(8) -0.0009(8) F42 0.0527(7) 0.0589(7) 0.0631(8) -0.0031(6) 0.0038(6) 0.0094(5) C42 0.0552(11) 0.0384(10) 0.0478(11) -0.0060(8) 0.0067(9) 0.0023(8) F43 0.1062(11) 0.0540(7) 0.0580(8) 0.0133(6) 0.0007(7) 0.0100(7) C43 0.0775(15) 0.0408(11) 0.0481(12) 0.0043(9) 0.0072(10) 0.0030(10) F44 0.1259(14) 0.0928(12) 0.1008(13) 0.0366(10) 0.0428(11) -0.0203(10) C44 0.0885(17) 0.0534(13) 0.0665(15) 0.0126(11) 0.0256(13) -0.0091(12) F45 0.0637(9) 0.1139(13) 0.1326(15) 0.0275(12) 0.0320(9) -0.0181(9) C45 0.0565(13) 0.0650(14) 0.0821(17) 0.0073(13) 0.0221(12) -0.0110(11) F46 0.0496(7) 0.0693(8) 0.0823(9) 0.0154(7) 0.0002(6) 0.0009(6) C46 0.0522(11) 0.0481(11) 0.0568(12) 0.0044(9) 0.0065(9) -0.0004(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 C11 1.736(2) . ? P1 C2 1.759(2) . ? P1 C21 1.810(2) . ? P1 C5 1.822(2) . ? B1 C2 1.455(3) . ? B1 C31 1.593(3) . ? B1 C41 1.596(3) . ? C2 C3 1.469(3) . ? C3 C4 1.336(3) . ? C3 H3 0.9400 . ? C4 C6 1.498(3) . ? C4 C5 1.514(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C6 H6C 0.9700 . ? C11 C12 1.201(3) . ? C12 C13 1.434(3) . ? C13 C14 1.365(4) . ? C13 C15 1.436(4) . ? C14 H14A 0.94(3) . ? C14 H14B 0.92(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 H15C 0.9700 . ? C21 C26 1.413(3) . ? C21 C22 1.416(3) . ? C22 C23 1.389(3) . ? C22 C27 1.507(3) . ? C23 C24 1.376(3) . ? C23 H23 0.9400 . ? C24 C25 1.385(3) . ? C24 C28 1.511(3) . ? C25 C26 1.391(3) . ? C25 H25 0.9400 . ? C26 C29 1.510(3) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 H28C 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? C31 C32 1.382(3) . ? C31 C36 1.388(3) . ? F32 C32 1.351(2) . ? C32 C33 1.380(3) . ? F33 C33 1.342(3) . ? C33 C34 1.367(3) . ? F34 C34 1.341(3) . ? C34 C35 1.372(4) . ? F35 C35 1.344(3) . ? C35 C36 1.377(3) . ? F36 C36 1.346(3) . ? C41 C46 1.386(3) . ? C41 C42 1.388(3) . ? F42 C42 1.349(2) . ? C42 C43 1.370(3) . ? F43 C43 1.346(2) . ? C43 C44 1.368(4) . ? F44 C44 1.342(3) . ? C44 C45 1.374(4) . ? F45 C45 1.342(3) . ? C45 C46 1.376(3) . ? F46 C46 1.347(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 C11 P1 C2 110.66(10) . . ? C11 P1 C21 112.85(10) . . ? C2 P1 C21 115.03(9) . . ? C11 P1 C5 103.07(11) . . ? C2 P1 C5 98.19(10) . . ? C21 P1 C5 115.59(10) . . ? C2 B1 C31 123.18(18) . . ? C2 B1 C41 119.20(18) . . ? C31 B1 C41 117.57(17) . . ? B1 C2 C3 131.24(19) . . ? B1 C2 P1 125.25(15) . . ? C3 C2 P1 103.50(13) . . ? C4 C3 C2 119.99(19) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C6 127.1(2) . . ? C3 C4 C5 114.74(18) . . ? C6 C4 C5 118.14(19) . . ? C4 C5 P1 102.64(14) . . ? C4 C5 H5A 111.2 . . ? P1 C5 H5A 111.2 . . ? C4 C5 H5B 111.2 . . ? P1 C5 H5B 111.2 . . ? H5A C5 H5B 109.2 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C12 C11 P1 162.9(2) . . ? C11 C12 C13 178.0(3) . . ? C14 C13 C12 118.7(3) . . ? C14 C13 C15 124.7(3) . . ? C12 C13 C15 116.5(3) . . ? C13 C14 H14A 118(2) . . ? C13 C14 H14B 120(3) . . ? H14A C14 H14B 121(3) . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C26 C21 C22 119.90(18) . . ? C26 C21 P1 124.38(15) . . ? C22 C21 P1 115.42(14) . . ? C23 C22 C21 118.46(19) . . ? C23 C22 C27 116.51(18) . . ? C21 C22 C27 125.03(18) . . ? C24 C23 C22 122.7(2) . . ? C24 C23 H23 118.6 . . ? C22 C23 H23 118.6 . . ? C23 C24 C25 117.7(2) . . ? C23 C24 C28 120.6(2) . . ? C25 C24 C28 121.7(2) . . ? C24 C25 C26 122.9(2) . . ? C24 C25 H25 118.5 . . ? C26 C25 H25 118.5 . . ? C25 C26 C21 118.01(19) . . ? C25 C26 C29 116.8(2) . . ? C21 C26 C29 125.2(2) . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C24 C28 H28A 109.5 . . ? C24 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C24 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C32 C31 C36 114.05(19) . . ? C32 C31 B1 123.75(17) . . ? C36 C31 B1 122.13(18) . . ? F32 C32 C33 116.20(19) . . ? F32 C32 C31 119.91(18) . . ? C33 C32 C31 123.85(19) . . ? F33 C33 C34 119.4(2) . . ? F33 C33 C32 121.0(2) . . ? C34 C33 C32 119.6(2) . . ? F34 C34 C33 120.5(2) . . ? F34 C34 C35 120.3(2) . . ? C33 C34 C35 119.2(2) . . ? F35 C35 C34 119.8(2) . . ? F35 C35 C36 120.7(2) . . ? C34 C35 C36 119.6(2) . . ? F36 C36 C35 117.3(2) . . ? F36 C36 C31 119.0(2) . . ? C35 C36 C31 123.7(2) . . ? C46 C41 C42 114.63(19) . . ? C46 C41 B1 124.15(17) . . ? C42 C41 B1 120.99(17) . . ? F42 C42 C43 117.36(18) . . ? F42 C42 C41 118.79(18) . . ? C43 C42 C41 123.8(2) . . ? F43 C43 C44 119.7(2) . . ? F43 C43 C42 121.2(2) . . ? C44 C43 C42 119.2(2) . . ? F44 C44 C43 120.5(2) . . ? F44 C44 C45 119.7(2) . . ? C43 C44 C45 119.7(2) . . ? F45 C45 C44 119.8(2) . . ? F45 C45 C46 120.7(2) . . ? C44 C45 C46 119.6(2) . . ? F46 C46 C45 117.46(19) . . ? F46 C46 C41 119.51(19) . . ? C45 C46 C41 123.0(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 C31 B1 C2 C3 5.3(3) . . . . ? C41 B1 C2 C3 -177.31(18) . . . . ? C31 B1 C2 P1 -174.37(14) . . . . ? C41 B1 C2 P1 3.0(3) . . . . ? C11 P1 C2 B1 -81.24(19) . . . . ? C21 P1 C2 B1 48.11(19) . . . . ? C5 P1 C2 B1 171.39(17) . . . . ? C11 P1 C2 C3 99.01(14) . . . . ? C21 P1 C2 C3 -131.64(12) . . . . ? C5 P1 C2 C3 -8.35(14) . . . . ? B1 C2 C3 C4 -174.0(2) . . . . ? P1 C2 C3 C4 5.7(2) . . . . ? C2 C3 C4 C6 -177.3(2) . . . . ? C2 C3 C4 C5 0.9(3) . . . . ? C3 C4 C5 P1 -6.8(2) . . . . ? C6 C4 C5 P1 171.57(17) . . . . ? C11 P1 C5 C4 -104.72(15) . . . . ? C2 P1 C5 C4 8.81(15) . . . . ? C21 P1 C5 C4 131.70(14) . . . . ? C2 P1 C11 C12 -48.2(7) . . . . ? C21 P1 C11 C12 -178.7(7) . . . . ? C5 P1 C11 C12 55.9(7) . . . . ? P1 C11 C12 C13 111(7) . . . . ? C11 C12 C13 C14 -163(7) . . . . ? C11 C12 C13 C15 16(7) . . . . ? C11 P1 C21 C26 4.2(2) . . . . ? C2 P1 C21 C26 -124.03(17) . . . . ? C5 P1 C21 C26 122.52(18) . . . . ? C11 P1 C21 C22 177.93(14) . . . . ? C2 P1 C21 C22 49.67(17) . . . . ? C5 P1 C21 C22 -63.79(17) . . . . ? C26 C21 C22 C23 3.8(3) . . . . ? P1 C21 C22 C23 -170.22(15) . . . . ? C26 C21 C22 C27 -176.02(19) . . . . ? P1 C21 C22 C27 10.0(3) . . . . ? C21 C22 C23 C24 0.5(3) . . . . ? C27 C22 C23 C24 -179.7(2) . . . . ? C22 C23 C24 C25 -3.9(3) . . . . ? C22 C23 C24 C28 176.5(2) . . . . ? C23 C24 C25 C26 3.2(3) . . . . ? C28 C24 C25 C26 -177.2(2) . . . . ? C24 C25 C26 C21 0.9(3) . . . . ? C24 C25 C26 C29 -178.8(2) . . . . ? C22 C21 C26 C25 -4.4(3) . . . . ? P1 C21 C26 C25 169.00(16) . . . . ? C22 C21 C26 C29 175.2(2) . . . . ? P1 C21 C26 C29 -11.3(3) . . . . ? C2 B1 C31 C32 50.8(3) . . . . ? C41 B1 C31 C32 -126.64(19) . . . . ? C2 B1 C31 C36 -132.5(2) . . . . ? C41 B1 C31 C36 50.0(3) . . . . ? C36 C31 C32 F32 -178.19(18) . . . . ? B1 C31 C32 F32 -1.3(3) . . . . ? C36 C31 C32 C33 -0.6(3) . . . . ? B1 C31 C32 C33 176.30(19) . . . . ? F32 C32 C33 F33 -1.0(3) . . . . ? C31 C32 C33 F33 -178.65(18) . . . . ? F32 C32 C33 C34 178.57(19) . . . . ? C31 C32 C33 C34 0.9(3) . . . . ? F33 C33 C34 F34 -0.1(3) . . . . ? C32 C33 C34 F34 -179.7(2) . . . . ? F33 C33 C34 C35 179.4(2) . . . . ? C32 C33 C34 C35 -0.1(3) . . . . ? F34 C34 C35 F35 -1.1(4) . . . . ? C33 C34 C35 F35 179.3(2) . . . . ? F34 C34 C35 C36 178.7(2) . . . . ? C33 C34 C35 C36 -0.9(4) . . . . ? F35 C35 C36 F36 0.9(4) . . . . ? C34 C35 C36 F36 -178.9(2) . . . . ? F35 C35 C36 C31 -179.0(2) . . . . ? C34 C35 C36 C31 1.2(4) . . . . ? C32 C31 C36 F36 179.67(19) . . . . ? B1 C31 C36 F36 2.7(3) . . . . ? C32 C31 C36 C35 -0.5(3) . . . . ? B1 C31 C36 C35 -177.4(2) . . . . ? C2 B1 C41 C46 76.6(3) . . . . ? C31 B1 C41 C46 -105.8(2) . . . . ? C2 B1 C41 C42 -97.6(2) . . . . ? C31 B1 C41 C42 79.9(2) . . . . ? C46 C41 C42 F42 178.79(17) . . . . ? B1 C41 C42 F42 -6.4(3) . . . . ? C46 C41 C42 C43 -2.2(3) . . . . ? B1 C41 C42 C43 172.59(19) . . . . ? F42 C42 C43 F43 1.3(3) . . . . ? C41 C42 C43 F43 -177.77(18) . . . . ? F42 C42 C43 C44 -178.9(2) . . . . ? C41 C42 C43 C44 2.0(3) . . . . ? F43 C43 C44 F44 -0.3(4) . . . . ? C42 C43 C44 F44 179.9(2) . . . . ? F43 C43 C44 C45 179.4(2) . . . . ? C42 C43 C44 C45 -0.4(4) . . . . ? F44 C44 C45 F45 0.5(4) . . . . ? C43 C44 C45 F45 -179.2(2) . . . . ? F44 C44 C45 C46 178.9(2) . . . . ? C43 C44 C45 C46 -0.8(4) . . . . ? F45 C45 C46 F46 -1.2(4) . . . . ? C44 C45 C46 F46 -179.6(2) . . . . ? F45 C45 C46 C41 179.0(2) . . . . ? C44 C45 C46 C41 0.6(4) . . . . ? C42 C41 C46 F46 -179.00(18) . . . . ? B1 C41 C46 F46 6.4(3) . . . . ? C42 C41 C46 C45 0.9(3) . . . . ? B1 C41 C46 C45 -173.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 67.11 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.255 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.038 _database_code_depnum_ccdc_archive 'CCDC 956697' ####################################################################### # # 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_erk7120 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H30 B F10 P' _chemical_formula_weight 706.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 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 12.6876(2) _cell_length_b 16.4138(2) _cell_length_c 16.9396(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.0680(10) _cell_angle_gamma 90.00 _cell_volume 3353.75(9) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6911 _cell_measurement_theta_min 4.08 _cell_measurement_theta_max 28.28 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1448 _exptl_absorpt_coefficient_mu 0.164 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9524 _exptl_absorpt_correction_T_max 0.9838 _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 20024 _diffrn_reflns_av_R_equivalents 0.032 _diffrn_reflns_av_sigmaI/netI 0.0323 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.09 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5809 _reflns_number_gt 4852 _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^)+(0.0519P)^2^+2.8096P] 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 5809 _refine_ls_number_parameters 445 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0662 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1428 _refine_ls_wR_factor_gt 0.1324 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 0.23679(5) 0.22729(4) 0.47712(4) 0.03610(17) Uani 1 1 d . . . C11 C 0.1052(2) 0.20501(16) 0.48171(17) 0.0442(6) Uani 1 1 d . . . C12 C 0.0148(2) 0.18129(17) 0.47763(17) 0.0482(6) Uani 1 1 d . . . C2 C 0.27022(19) 0.15913(14) 0.40784(15) 0.0375(5) Uani 1 1 d . . . C3 C 0.36562(19) 0.11365(15) 0.46111(15) 0.0389(5) Uani 1 1 d . . . H3 H 0.4001 0.0736 0.4380 0.047 Uiso 1 1 calc R . . C4 C 0.40314(19) 0.12924(15) 0.54204(15) 0.0396(5) Uani 1 1 d . . . C9 C 0.5024(2) 0.09376(17) 0.60625(17) 0.0508(7) Uani 1 1 d . . . H9A H 0.5459 0.0616 0.5787 0.061 Uiso 1 1 calc R . . H9B H 0.4777 0.0573 0.6429 0.061 Uiso 1 1 calc R . . C8 C 0.5746(2) 0.1610(2) 0.65764(19) 0.0577(8) Uani 1 1 d . . . H8A H 0.6356 0.1365 0.7018 0.069 Uiso 1 1 calc R . . H8B H 0.6068 0.1932 0.6222 0.069 Uiso 1 1 calc R . . C7 C 0.5082(2) 0.2164(2) 0.69587(19) 0.0619(8) Uani 1 1 d . . . H7A H 0.5569 0.2585 0.7291 0.074 Uiso 1 1 calc R . . H7B H 0.4781 0.1846 0.7329 0.074 Uiso 1 1 calc R . . C6 C 0.4127(2) 0.25698(18) 0.62868(17) 0.0539(7) Uani 1 1 d . . . H6A H 0.3688 0.2904 0.6549 0.065 Uiso 1 1 calc R . . H6B H 0.4428 0.2928 0.5946 0.065 Uiso 1 1 calc R . . C5 C 0.33883(19) 0.19256(16) 0.57387(15) 0.0406(6) Uani 1 1 d . . . H5 H 0.2984 0.1641 0.6072 0.049 Uiso 1 1 calc R . . C13 C -0.0967(2) 0.15592(18) 0.46907(18) 0.0521(7) Uani 1 1 d . . . C14 C -0.1746(3) 0.2139(2) 0.4713(3) 0.0831(12) Uani 1 1 d . . . H14 H -0.1533 0.2685 0.4833 0.100 Uiso 1 1 calc R . . C15 C -0.2931(3) 0.1894(3) 0.4546(4) 0.1142(17) Uani 1 1 d . . . H15A H -0.3226 0.2176 0.4943 0.137 Uiso 1 1 calc R . . H15B H -0.3356 0.2080 0.3989 0.137 Uiso 1 1 calc R . . C16 C -0.3111(3) 0.1022(3) 0.4603(3) 0.1013(15) Uani 1 1 d . . . H16A H -0.2950 0.0876 0.5189 0.122 Uiso 1 1 calc R . . H16B H -0.3896 0.0904 0.4324 0.122 Uiso 1 1 calc R . . C17 C -0.2451(4) 0.0516(3) 0.4245(4) 0.129(2) Uani 1 1 d . . . H17A H -0.2728 0.0571 0.3640 0.155 Uiso 1 1 calc R . . H17B H -0.2548 -0.0054 0.4381 0.155 Uiso 1 1 calc R . . C18 C -0.1244(3) 0.0714(2) 0.4535(3) 0.0807(11) Uani 1 1 d . . . H18A H -0.0897 0.0409 0.5047 0.097 Uiso 1 1 calc R . . H18B H -0.0917 0.0520 0.4116 0.097 Uiso 1 1 calc R . . C21 C 0.24786(19) 0.33565(15) 0.45914(15) 0.0402(6) Uani 1 1 d . . . C22 C 0.1733(2) 0.39386(17) 0.47328(18) 0.0522(7) Uani 1 1 d . . . C23 C 0.1816(3) 0.47369(19) 0.4496(2) 0.0691(9) Uani 1 1 d . . . H23 H 0.1310 0.5122 0.4576 0.083 Uiso 1 1 calc R . . C24 C 0.2604(3) 0.4993(2) 0.4149(2) 0.0752(10) Uani 1 1 d . . . C25 C 0.3374(3) 0.4434(2) 0.4073(2) 0.0673(9) Uani 1 1 d . . . H25 H 0.3943 0.4609 0.3867 0.081 Uiso 1 1 calc R . . C26 C 0.3342(2) 0.36178(16) 0.42892(17) 0.0490(6) Uani 1 1 d . . . C27 C 0.0878(3) 0.3755(2) 0.5172(2) 0.0702(9) Uani 1 1 d . . . H27A H 0.0651 0.4259 0.5371 0.105 Uiso 1 1 calc R . . H27B H 0.1202 0.3394 0.5638 0.105 Uiso 1 1 calc R . . H27C H 0.0238 0.3494 0.4787 0.105 Uiso 1 1 calc R . . C28 C 0.2643(5) 0.5877(2) 0.3884(4) 0.1245(19) Uani 1 1 d . . . H28A H 0.2449 0.5906 0.3284 0.187 Uiso 1 1 calc R . . H28B H 0.3385 0.6092 0.4132 0.187 Uiso 1 1 calc R . . H28C H 0.2119 0.6197 0.4067 0.187 Uiso 1 1 calc R . . C29 C 0.4270(2) 0.30812(19) 0.4206(2) 0.0603(8) Uani 1 1 d . . . H29A H 0.4045 0.2823 0.3665 0.090 Uiso 1 1 calc R . . H29B H 0.4434 0.2666 0.4635 0.090 Uiso 1 1 calc R . . H29C H 0.4925 0.3410 0.4267 0.090 Uiso 1 1 calc R . . B1 B 0.2136(2) 0.15282(18) 0.31967(18) 0.0420(6) Uani 1 1 d . . . C31 C 0.1133(2) 0.21340(17) 0.27429(15) 0.0463(6) Uani 1 1 d . . . F32 F -0.02560(14) 0.13303(12) 0.30250(12) 0.0680(5) Uani 1 1 d . . . C32 C 0.0037(2) 0.2014(2) 0.27254(17) 0.0546(7) Uani 1 1 d . . . F33 F -0.18229(15) 0.24488(16) 0.24188(15) 0.0967(7) Uani 1 1 d . . . C33 C -0.0783(3) 0.2584(2) 0.2405(2) 0.0684(9) Uani 1 1 d . . . F34 F -0.1333(2) 0.38476(15) 0.17588(16) 0.1114(9) Uani 1 1 d . . . C34 C -0.0538(3) 0.3290(2) 0.2077(2) 0.0748(10) Uani 1 1 d . . . F35 F 0.0781(2) 0.41184(14) 0.17325(15) 0.1054(8) Uani 1 1 d . . . C35 C 0.0521(3) 0.3433(2) 0.2056(2) 0.0711(10) Uani 1 1 d . . . F36 F 0.23630(16) 0.30033(12) 0.23583(12) 0.0712(5) Uani 1 1 d . . . C36 C 0.1328(2) 0.28501(19) 0.23895(17) 0.0554(7) Uani 1 1 d . . . C41 C 0.2525(2) 0.08880(17) 0.26324(16) 0.0469(6) Uani 1 1 d . . . F42 F 0.07498(15) 0.02990(12) 0.21159(13) 0.0779(6) Uani 1 1 d . . . C42 C 0.1819(3) 0.03154(19) 0.21390(18) 0.0589(8) Uani 1 1 d . . . F43 F 0.1426(2) -0.08109(14) 0.12246(15) 0.1084(9) Uani 1 1 d . . . C43 C 0.2150(3) -0.0253(2) 0.1666(2) 0.0710(9) Uani 1 1 d . . . F44 F 0.3543(2) -0.08012(15) 0.11852(13) 0.1073(9) Uani 1 1 d . . . C44 C 0.3213(3) -0.0251(2) 0.1643(2) 0.0716(10) Uani 1 1 d . . . F45 F 0.50011(17) 0.03210(14) 0.20907(13) 0.0874(7) Uani 1 1 d . . . C45 C 0.3946(3) 0.0307(2) 0.21024(19) 0.0621(8) Uani 1 1 d . . . F46 F 0.43634(13) 0.13873(11) 0.30349(10) 0.0608(4) Uani 1 1 d . . . C46 C 0.3597(2) 0.08550(17) 0.25927(16) 0.0498(7) 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 0.0294(3) 0.0404(3) 0.0403(3) -0.0014(3) 0.0136(2) 0.0014(2) C11 0.0366(13) 0.0463(14) 0.0527(15) -0.0042(12) 0.0181(11) 0.0019(11) C12 0.0385(14) 0.0536(16) 0.0567(16) -0.0006(13) 0.0208(12) 0.0021(12) C2 0.0341(12) 0.0392(12) 0.0413(13) -0.0011(10) 0.0147(10) 0.0024(10) C3 0.0358(12) 0.0368(12) 0.0464(14) -0.0004(11) 0.0162(11) 0.0034(10) C4 0.0351(12) 0.0401(13) 0.0447(14) 0.0038(11) 0.0138(10) 0.0016(10) C9 0.0439(14) 0.0535(16) 0.0518(16) 0.0110(13) 0.0102(12) 0.0099(12) C8 0.0381(14) 0.073(2) 0.0549(17) 0.0067(15) 0.0048(12) 0.0039(13) C7 0.0506(16) 0.077(2) 0.0496(16) -0.0065(15) 0.0029(13) 0.0010(15) C6 0.0494(15) 0.0594(17) 0.0487(16) -0.0102(13) 0.0089(12) 0.0039(13) C5 0.0351(12) 0.0487(14) 0.0395(13) -0.0003(11) 0.0137(10) 0.0004(11) C13 0.0355(13) 0.0623(18) 0.0619(17) 0.0023(14) 0.0202(12) -0.0037(12) C14 0.0508(18) 0.070(2) 0.140(4) 0.000(2) 0.045(2) 0.0051(16) C15 0.052(2) 0.123(4) 0.181(5) 0.027(4) 0.053(3) 0.015(2) C16 0.048(2) 0.121(4) 0.140(4) 0.003(3) 0.036(2) -0.020(2) C17 0.076(3) 0.121(4) 0.205(6) -0.039(4) 0.065(3) -0.049(3) C18 0.0559(19) 0.071(2) 0.123(3) -0.006(2) 0.039(2) -0.0102(17) C21 0.0375(12) 0.0392(13) 0.0425(13) -0.0015(11) 0.0101(10) 0.0022(10) C22 0.0433(14) 0.0495(15) 0.0583(17) -0.0070(13) 0.0078(12) 0.0069(12) C23 0.072(2) 0.0486(17) 0.080(2) 0.0001(16) 0.0146(18) 0.0195(15) C24 0.101(3) 0.0458(17) 0.080(2) 0.0113(16) 0.030(2) 0.0080(18) C25 0.082(2) 0.0543(18) 0.074(2) 0.0077(16) 0.0367(18) -0.0053(16) C26 0.0534(16) 0.0442(14) 0.0524(16) 0.0014(12) 0.0211(13) -0.0021(12) C27 0.0554(18) 0.0605(19) 0.102(3) -0.0207(18) 0.0346(18) 0.0076(15) C28 0.179(5) 0.055(2) 0.151(5) 0.035(3) 0.067(4) 0.018(3) C29 0.0522(16) 0.0563(17) 0.085(2) -0.0021(16) 0.0405(16) -0.0080(14) B1 0.0381(14) 0.0453(16) 0.0434(15) 0.0005(13) 0.0136(12) 0.0033(12) C31 0.0444(14) 0.0574(16) 0.0364(13) -0.0038(12) 0.0114(11) 0.0100(12) F32 0.0484(9) 0.0805(13) 0.0723(12) -0.0024(10) 0.0145(8) -0.0061(9) C32 0.0437(15) 0.0695(19) 0.0453(15) -0.0075(14) 0.0063(12) 0.0082(14) F33 0.0406(10) 0.1275(19) 0.1122(17) -0.0230(15) 0.0095(10) 0.0207(11) C33 0.0472(17) 0.086(2) 0.064(2) -0.0156(18) 0.0052(14) 0.0205(16) F34 0.0998(17) 0.1028(17) 0.1092(18) 0.0025(14) -0.0006(14) 0.0630(14) C34 0.063(2) 0.080(2) 0.070(2) -0.0051(19) 0.0045(17) 0.0351(19) F35 0.137(2) 0.0751(14) 0.0992(17) 0.0342(13) 0.0293(15) 0.0265(14) C35 0.097(3) 0.060(2) 0.0495(18) 0.0100(15) 0.0135(17) 0.0204(18) F36 0.0746(12) 0.0779(12) 0.0692(12) 0.0172(10) 0.0340(10) 0.0048(10) C36 0.0564(17) 0.0667(19) 0.0446(15) 0.0051(14) 0.0181(13) 0.0149(14) C41 0.0507(15) 0.0514(15) 0.0373(13) 0.0025(12) 0.0116(11) 0.0104(12) F42 0.0558(11) 0.0826(13) 0.0863(13) -0.0287(11) 0.0088(9) -0.0024(9) C42 0.0597(18) 0.0605(18) 0.0503(16) -0.0064(14) 0.0083(14) 0.0125(14) F43 0.1187(19) 0.0872(15) 0.0985(17) -0.0504(14) 0.0033(14) 0.0042(14) C43 0.084(2) 0.063(2) 0.0542(18) -0.0149(16) 0.0039(17) 0.0163(18) F44 0.143(2) 0.1040(17) 0.0751(14) -0.0252(12) 0.0344(14) 0.0556(16) C44 0.096(3) 0.067(2) 0.0494(18) -0.0071(16) 0.0202(17) 0.037(2) F45 0.0827(13) 0.1151(17) 0.0807(13) 0.0058(12) 0.0490(11) 0.0382(12) C45 0.070(2) 0.073(2) 0.0496(17) 0.0120(16) 0.0290(15) 0.0308(17) F46 0.0507(9) 0.0761(11) 0.0618(10) -0.0011(9) 0.0268(8) 0.0022(8) C46 0.0559(16) 0.0550(16) 0.0396(14) 0.0061(12) 0.0165(12) 0.0131(13) _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 1.734(3) . ? P1 C2 1.766(2) . ? P1 C21 1.817(3) . ? P1 C5 1.836(2) . ? C11 C12 1.193(3) . ? C12 C13 1.438(4) . ? C2 B1 1.446(4) . ? C2 C3 1.469(3) . ? C3 C4 1.329(3) . ? C3 H3 0.9400 . ? C4 C9 1.503(3) . ? C4 C5 1.520(3) . ? C9 C8 1.524(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C8 C7 1.515(4) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C7 C6 1.533(4) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C6 C5 1.523(4) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C5 H5 0.9900 . ? C13 C14 1.382(4) . ? C13 C18 1.435(5) . ? C14 C15 1.496(5) . ? C14 H14 0.9400 . ? C15 C16 1.457(6) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C16 C17 1.439(6) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C17 C18 1.492(5) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C21 C26 1.413(4) . ? C21 C22 1.416(4) . ? C22 C23 1.384(4) . ? C22 C27 1.524(4) . ? C23 C24 1.373(5) . ? C23 H23 0.9400 . ? C24 C25 1.375(5) . ? C24 C28 1.525(5) . ? C25 C26 1.393(4) . ? C25 H25 0.9400 . ? C26 C29 1.510(4) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 H28C 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? B1 C41 1.598(4) . ? B1 C31 1.610(4) . ? C31 C36 1.376(4) . ? C31 C32 1.395(4) . ? F32 C32 1.332(4) . ? C32 C33 1.380(4) . ? F33 C33 1.345(4) . ? C33 C34 1.361(5) . ? F34 C34 1.345(4) . ? C34 C35 1.374(5) . ? F35 C35 1.337(4) . ? C35 C36 1.387(4) . ? F36 C36 1.354(3) . ? C41 C46 1.384(4) . ? C41 C42 1.386(4) . ? F42 C42 1.345(3) . ? C42 C43 1.378(4) . ? F43 C43 1.348(4) . ? C43 C44 1.360(5) . ? F44 C44 1.340(3) . ? C44 C45 1.365(5) . ? F45 C45 1.345(4) . ? C45 C46 1.386(4) . ? F46 C46 1.348(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 P1 C2 109.22(12) . . ? C11 P1 C21 109.84(12) . . ? C2 P1 C21 117.50(12) . . ? C11 P1 C5 108.46(12) . . ? C2 P1 C5 98.53(11) . . ? C21 P1 C5 112.56(12) . . ? C12 C11 P1 171.1(3) . . ? C11 C12 C13 176.8(3) . . ? B1 C2 C3 130.4(2) . . ? B1 C2 P1 125.93(19) . . ? C3 C2 P1 103.63(17) . . ? C4 C3 C2 119.9(2) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C9 128.6(2) . . ? C3 C4 C5 116.0(2) . . ? C9 C4 C5 115.4(2) . . ? C4 C9 C8 110.7(2) . . ? C4 C9 H9A 109.5 . . ? C8 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C7 C8 C9 111.3(2) . . ? C7 C8 H8A 109.4 . . ? C9 C8 H8A 109.4 . . ? C7 C8 H8B 109.4 . . ? C9 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? C8 C7 C6 111.1(2) . . ? C8 C7 H7A 109.4 . . ? C6 C7 H7A 109.4 . . ? C8 C7 H7B 109.4 . . ? C6 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C5 C6 C7 110.2(2) . . ? C5 C6 H6A 109.6 . . ? C7 C6 H6A 109.6 . . ? C5 C6 H6B 109.6 . . ? C7 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C4 C5 C6 113.2(2) . . ? C4 C5 P1 101.72(16) . . ? C6 C5 P1 117.32(19) . . ? C4 C5 H5 108.0 . . ? C6 C5 H5 108.0 . . ? P1 C5 H5 108.0 . . ? C14 C13 C18 122.3(3) . . ? C14 C13 C12 119.2(3) . . ? C18 C13 C12 118.4(3) . . ? C13 C14 C15 119.7(4) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C16 C15 C14 114.8(3) . . ? C16 C15 H15A 108.6 . . ? C14 C15 H15A 108.6 . . ? C16 C15 H15B 108.6 . . ? C14 C15 H15B 108.6 . . ? H15A C15 H15B 107.5 . . ? C17 C16 C15 114.6(4) . . ? C17 C16 H16A 108.6 . . ? C15 C16 H16A 108.6 . . ? C17 C16 H16B 108.6 . . ? C15 C16 H16B 108.6 . . ? H16A C16 H16B 107.6 . . ? C16 C17 C18 114.1(4) . . ? C16 C17 H17A 108.7 . . ? C18 C17 H17A 108.7 . . ? C16 C17 H17B 108.7 . . ? C18 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C13 C18 C17 116.1(3) . . ? C13 C18 H18A 108.3 . . ? C17 C18 H18A 108.3 . . ? C13 C18 H18B 108.3 . . ? C17 C18 H18B 108.3 . . ? H18A C18 H18B 107.4 . . ? C26 C21 C22 119.4(2) . . ? C26 C21 P1 117.83(19) . . ? C22 C21 P1 122.8(2) . . ? C23 C22 C21 118.3(3) . . ? C23 C22 C27 117.3(3) . . ? C21 C22 C27 124.3(3) . . ? C24 C23 C22 123.0(3) . . ? C24 C23 H23 118.5 . . ? C22 C23 H23 118.5 . . ? C23 C24 C25 117.9(3) . . ? C23 C24 C28 120.8(4) . . ? C25 C24 C28 121.3(4) . . ? C24 C25 C26 122.6(3) . . ? C24 C25 H25 118.7 . . ? C26 C25 H25 118.7 . . ? C25 C26 C21 118.4(3) . . ? C25 C26 C29 116.7(3) . . ? C21 C26 C29 124.8(2) . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C24 C28 H28A 109.5 . . ? C24 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C24 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C2 B1 C41 121.2(2) . . ? C2 B1 C31 121.0(2) . . ? C41 B1 C31 117.7(2) . . ? C36 C31 C32 115.1(3) . . ? C36 C31 B1 120.9(2) . . ? C32 C31 B1 123.9(3) . . ? F32 C32 C33 117.1(3) . . ? F32 C32 C31 120.3(3) . . ? C33 C32 C31 122.6(3) . . ? F33 C33 C34 119.9(3) . . ? F33 C33 C32 120.3(4) . . ? C34 C33 C32 119.8(3) . . ? F34 C34 C33 120.3(4) . . ? F34 C34 C35 119.4(4) . . ? C33 C34 C35 120.3(3) . . ? F35 C35 C34 121.4(3) . . ? F35 C35 C36 120.1(4) . . ? C34 C35 C36 118.4(3) . . ? F36 C36 C31 118.9(2) . . ? F36 C36 C35 117.3(3) . . ? C31 C36 C35 123.8(3) . . ? C46 C41 C42 113.9(3) . . ? C46 C41 B1 123.1(2) . . ? C42 C41 B1 123.0(2) . . ? F42 C42 C43 117.2(3) . . ? F42 C42 C41 119.2(3) . . ? C43 C42 C41 123.6(3) . . ? F43 C43 C44 119.8(3) . . ? F43 C43 C42 120.3(3) . . ? C44 C43 C42 119.9(3) . . ? F44 C44 C43 120.4(4) . . ? F44 C44 C45 120.1(3) . . ? C43 C44 C45 119.5(3) . . ? F45 C45 C44 120.6(3) . . ? F45 C45 C46 120.2(3) . . ? C44 C45 C46 119.3(3) . . ? F46 C46 C41 119.9(2) . . ? F46 C46 C45 116.3(3) . . ? C41 C46 C45 123.8(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 P1 C11 C12 1.9(17) . . . . ? C21 P1 C11 C12 132.1(17) . . . . ? C5 P1 C11 C12 -104.5(17) . . . . ? P1 C11 C12 C13 -94(6) . . . . ? C11 P1 C2 B1 63.7(3) . . . . ? C21 P1 C2 B1 -62.3(3) . . . . ? C5 P1 C2 B1 176.7(2) . . . . ? C11 P1 C2 C3 -116.46(17) . . . . ? C21 P1 C2 C3 117.61(17) . . . . ? C5 P1 C2 C3 -3.42(18) . . . . ? B1 C2 C3 C4 -179.0(3) . . . . ? P1 C2 C3 C4 1.2(3) . . . . ? C2 C3 C4 C9 -176.2(2) . . . . ? C2 C3 C4 C5 2.4(3) . . . . ? C3 C4 C9 C8 129.8(3) . . . . ? C5 C4 C9 C8 -48.8(3) . . . . ? C4 C9 C8 C7 54.7(3) . . . . ? C9 C8 C7 C6 -59.9(3) . . . . ? C8 C7 C6 C5 56.5(3) . . . . ? C3 C4 C5 C6 -131.3(2) . . . . ? C9 C4 C5 C6 47.5(3) . . . . ? C3 C4 C5 P1 -4.5(3) . . . . ? C9 C4 C5 P1 174.28(19) . . . . ? C7 C6 C5 C4 -49.7(3) . . . . ? C7 C6 C5 P1 -167.8(2) . . . . ? C11 P1 C5 C4 118.11(17) . . . . ? C2 P1 C5 C4 4.46(18) . . . . ? C21 P1 C5 C4 -120.14(17) . . . . ? C11 P1 C5 C6 -117.8(2) . . . . ? C2 P1 C5 C6 128.6(2) . . . . ? C21 P1 C5 C6 4.0(2) . . . . ? C11 C12 C13 C14 -52(6) . . . . ? C11 C12 C13 C18 124(6) . . . . ? C18 C13 C14 C15 -1.8(6) . . . . ? C12 C13 C14 C15 174.3(4) . . . . ? C13 C14 C15 C16 16.6(7) . . . . ? C14 C15 C16 C17 -41.1(7) . . . . ? C15 C16 C17 C18 50.5(7) . . . . ? C14 C13 C18 C17 10.8(6) . . . . ? C12 C13 C18 C17 -165.4(4) . . . . ? C16 C17 C18 C13 -34.9(7) . . . . ? C11 P1 C21 C26 -161.3(2) . . . . ? C2 P1 C21 C26 -35.6(2) . . . . ? C5 P1 C21 C26 77.8(2) . . . . ? C11 P1 C21 C22 18.0(3) . . . . ? C2 P1 C21 C22 143.6(2) . . . . ? C5 P1 C21 C22 -102.9(2) . . . . ? C26 C21 C22 C23 5.9(4) . . . . ? P1 C21 C22 C23 -173.4(2) . . . . ? C26 C21 C22 C27 -170.7(3) . . . . ? P1 C21 C22 C27 10.0(4) . . . . ? C21 C22 C23 C24 -1.6(5) . . . . ? C27 C22 C23 C24 175.3(3) . . . . ? C22 C23 C24 C25 -3.2(6) . . . . ? C22 C23 C24 C28 178.8(4) . . . . ? C23 C24 C25 C26 3.7(6) . . . . ? C28 C24 C25 C26 -178.3(4) . . . . ? C24 C25 C26 C21 0.6(5) . . . . ? C24 C25 C26 C29 -177.5(3) . . . . ? C22 C21 C26 C25 -5.4(4) . . . . ? P1 C21 C26 C25 173.9(2) . . . . ? C22 C21 C26 C29 172.5(3) . . . . ? P1 C21 C26 C29 -8.2(4) . . . . ? C3 C2 B1 C41 -0.3(4) . . . . ? P1 C2 B1 C41 179.55(19) . . . . ? C3 C2 B1 C31 -177.0(2) . . . . ? P1 C2 B1 C31 2.9(4) . . . . ? C2 B1 C31 C36 91.9(3) . . . . ? C41 B1 C31 C36 -84.9(3) . . . . ? C2 B1 C31 C32 -83.3(3) . . . . ? C41 B1 C31 C32 99.8(3) . . . . ? C36 C31 C32 F32 177.8(2) . . . . ? B1 C31 C32 F32 -6.7(4) . . . . ? C36 C31 C32 C33 -2.3(4) . . . . ? B1 C31 C32 C33 173.3(3) . . . . ? F32 C32 C33 F33 1.5(4) . . . . ? C31 C32 C33 F33 -178.5(3) . . . . ? F32 C32 C33 C34 -178.9(3) . . . . ? C31 C32 C33 C34 1.2(5) . . . . ? F33 C33 C34 F34 -0.7(5) . . . . ? C32 C33 C34 F34 179.7(3) . . . . ? F33 C33 C34 C35 -179.7(3) . . . . ? C32 C33 C34 C35 0.6(5) . . . . ? F34 C34 C35 F35 0.5(5) . . . . ? C33 C34 C35 F35 179.6(3) . . . . ? F34 C34 C35 C36 179.8(3) . . . . ? C33 C34 C35 C36 -1.1(5) . . . . ? C32 C31 C36 F36 -178.1(2) . . . . ? B1 C31 C36 F36 6.2(4) . . . . ? C32 C31 C36 C35 1.7(4) . . . . ? B1 C31 C36 C35 -174.0(3) . . . . ? F35 C35 C36 F36 -1.0(5) . . . . ? C34 C35 C36 F36 179.7(3) . . . . ? F35 C35 C36 C31 179.2(3) . . . . ? C34 C35 C36 C31 -0.1(5) . . . . ? C2 B1 C41 C46 -55.0(4) . . . . ? C31 B1 C41 C46 121.8(3) . . . . ? C2 B1 C41 C42 124.9(3) . . . . ? C31 B1 C41 C42 -58.3(4) . . . . ? C46 C41 C42 F42 -178.8(3) . . . . ? B1 C41 C42 F42 1.2(4) . . . . ? C46 C41 C42 C43 1.6(4) . . . . ? B1 C41 C42 C43 -178.3(3) . . . . ? F42 C42 C43 F43 -2.0(5) . . . . ? C41 C42 C43 F43 177.5(3) . . . . ? F42 C42 C43 C44 178.0(3) . . . . ? C41 C42 C43 C44 -2.5(5) . . . . ? F43 C43 C44 F44 -0.1(5) . . . . ? C42 C43 C44 F44 180.0(3) . . . . ? F43 C43 C44 C45 -178.9(3) . . . . ? C42 C43 C44 C45 1.1(5) . . . . ? F44 C44 C45 F45 1.1(5) . . . . ? C43 C44 C45 F45 179.9(3) . . . . ? F44 C44 C45 C46 -178.0(3) . . . . ? C43 C44 C45 C46 0.9(5) . . . . ? C42 C41 C46 F46 179.1(2) . . . . ? B1 C41 C46 F46 -1.0(4) . . . . ? C42 C41 C46 C45 0.5(4) . . . . ? B1 C41 C46 C45 -179.6(3) . . . . ? F45 C45 C46 F46 0.5(4) . . . . ? C44 C45 C46 F46 179.6(3) . . . . ? F45 C45 C46 C41 179.2(3) . . . . ? C44 C45 C46 C41 -1.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.330 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 956698' ####################################################################### # # 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_erk7079 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C43 H42 B F10 P' _chemical_formula_weight 790.55 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 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 13.6441(2) _cell_length_b 18.2561(3) _cell_length_c 15.9218(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.5990(10) _cell_angle_gamma 90.00 _cell_volume 3965.71(11) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 8760 _cell_measurement_theta_min 4.08 _cell_measurement_theta_max 28.28 _exptl_crystal_description plate _exptl_crystal_colour green-yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1640 _exptl_absorpt_coefficient_mu 0.146 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9713 _exptl_absorpt_correction_T_max 0.9956 _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 28550 _diffrn_reflns_av_R_equivalents 0.061 _diffrn_reflns_av_sigmaI/netI 0.0518 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.11 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6883 _reflns_number_gt 4860 _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 group at C12 atom is disordered over two positions. Several restraints (SADI, SAME, ISOR and SIMU) 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^)+(0.0000P)^2^+5.6361P] 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 6883 _refine_ls_number_parameters 557 _refine_ls_number_restraints 87 _refine_ls_R_factor_all 0.1016 _refine_ls_R_factor_gt 0.0665 _refine_ls_wR_factor_ref 0.1314 _refine_ls_wR_factor_gt 0.1132 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.099 _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 0.43344(6) 0.24126(5) 0.29671(5) 0.0350(2) Uani 1 1 d . . . C11 C 0.5456(2) 0.19753(19) 0.28355(19) 0.0409(8) Uani 1 1 d . A . C2 C 0.3746(2) 0.24104(19) 0.19747(19) 0.0383(7) Uani 1 1 d . . . C3 C 0.3548(2) 0.31900(19) 0.1819(2) 0.0422(8) Uani 1 1 d . . . H3 H 0.3162 0.3331 0.1355 0.051 Uiso 1 1 calc R . . C4 C 0.3914(2) 0.36980(19) 0.2335(2) 0.0422(8) Uani 1 1 d . . . C5 C 0.4532(2) 0.33992(18) 0.30587(19) 0.0390(8) Uani 1 1 d . . . H5 H 0.5230 0.3504 0.2944 0.047 Uiso 1 1 calc R . . C6 C 0.4267(3) 0.37456(19) 0.3903(2) 0.0450(8) Uani 1 1 d . . . H6A H 0.3617 0.3577 0.4074 0.054 Uiso 1 1 calc R . . H6B H 0.4743 0.3592 0.4334 0.054 Uiso 1 1 calc R . . C7 C 0.4268(3) 0.4574(2) 0.3833(2) 0.0554(10) Uani 1 1 d . . . H7A H 0.4080 0.4788 0.4373 0.066 Uiso 1 1 calc R . . H7B H 0.4931 0.4744 0.3704 0.066 Uiso 1 1 calc R . . C8 C 0.3562(3) 0.4835(2) 0.3154(2) 0.0620(11) Uani 1 1 d . . . H8A H 0.3586 0.5371 0.3122 0.074 Uiso 1 1 calc R . . H8B H 0.2894 0.4693 0.3303 0.074 Uiso 1 1 calc R . . C9 C 0.3811(3) 0.4513(2) 0.2295(2) 0.0551(10) Uani 1 1 d . . . H9A H 0.3293 0.4640 0.1890 0.066 Uiso 1 1 calc R . . H9B H 0.4426 0.4727 0.2098 0.066 Uiso 1 1 calc R . . C12 C 0.6199(2) 0.1735(2) 0.2561(2) 0.0442(8) Uani 1 1 d D . . C13 C 0.702(3) 0.143(4) 0.212(3) 0.035(7) Uani 0.290(11) 1 d PDU A 1 C14 C 0.771(3) 0.103(3) 0.256(3) 0.055(8) Uani 0.290(11) 1 d PDU A 1 H14 H 0.7595 0.0918 0.3130 0.066 Uiso 0.290(11) 1 calc PR A 1 C15 C 0.864(3) 0.077(3) 0.2163(18) 0.076(8) Uani 0.290(11) 1 d PDU A 1 H15A H 0.8694 0.0242 0.2230 0.091 Uiso 0.290(11) 1 calc PR A 1 H15B H 0.9200 0.1000 0.2453 0.091 Uiso 0.290(11) 1 calc PR A 1 C16 C 0.8678(14) 0.0965(9) 0.1225(11) 0.062(5) Uani 0.290(11) 1 d PDU A 1 H16A H 0.9342 0.0895 0.1011 0.075 Uiso 0.290(11) 1 calc PR A 1 H16B H 0.8227 0.0653 0.0903 0.075 Uiso 0.290(11) 1 calc PR A 1 C17 C 0.8374(12) 0.1769(9) 0.1151(12) 0.060(5) Uani 0.290(11) 1 d PDU A 1 H17A H 0.8519 0.1959 0.0590 0.072 Uiso 0.290(11) 1 calc PR A 1 H17B H 0.8720 0.2068 0.1570 0.072 Uiso 0.290(11) 1 calc PR A 1 C18 C 0.7257(17) 0.178(2) 0.1308(18) 0.058(7) Uani 0.290(11) 1 d PDU A 1 H18A H 0.7021 0.2283 0.1306 0.070 Uiso 0.290(11) 1 calc PR A 1 H18B H 0.6920 0.1512 0.0854 0.070 Uiso 0.290(11) 1 calc PR A 1 C13A C 0.7114(15) 0.1502(15) 0.2210(12) 0.043(5) Uani 0.710(11) 1 d PDU A 2 C14A C 0.7613(13) 0.0923(14) 0.2548(10) 0.058(5) Uani 0.710(11) 1 d PDU A 2 H14A H 0.7363 0.0679 0.3019 0.070 Uiso 0.710(11) 1 calc PR A 2 C15A C 0.8560(11) 0.0675(10) 0.2171(9) 0.080(4) Uani 0.710(11) 1 d PDU A 2 H15C H 0.8450 0.0211 0.1876 0.096 Uiso 0.710(11) 1 calc PR A 2 H15D H 0.9037 0.0586 0.2623 0.096 Uiso 0.710(11) 1 calc PR A 2 C16A C 0.8989(5) 0.1234(4) 0.1555(5) 0.065(2) Uani 0.710(11) 1 d PDU A 2 H16C H 0.9224 0.1667 0.1861 0.078 Uiso 0.710(11) 1 calc PR A 2 H16D H 0.9544 0.1018 0.1257 0.078 Uiso 0.710(11) 1 calc PR A 2 C17A C 0.8183(5) 0.1452(5) 0.0929(4) 0.064(2) Uani 0.710(11) 1 d PDU A 2 H17C H 0.7912 0.1015 0.0656 0.077 Uiso 0.710(11) 1 calc PR A 2 H17D H 0.8452 0.1773 0.0494 0.077 Uiso 0.710(11) 1 calc PR A 2 C18A C 0.7381(8) 0.1853(9) 0.1411(8) 0.059(3) Uani 0.710(11) 1 d PDU A 2 H18C H 0.7602 0.2354 0.1528 0.071 Uiso 0.710(11) 1 calc PR A 2 H18D H 0.6794 0.1885 0.1053 0.071 Uiso 0.710(11) 1 calc PR A 2 C21 C 0.3713(2) 0.20292(17) 0.38805(18) 0.0340(7) Uani 1 1 d . . . C22 C 0.2674(2) 0.20378(19) 0.38962(19) 0.0392(8) Uani 1 1 d . . . C23 C 0.2206(2) 0.1609(2) 0.4490(2) 0.0452(8) Uani 1 1 d . . . H23 H 0.1517 0.1606 0.4496 0.054 Uiso 1 1 calc R . . C24 C 0.2704(2) 0.1187(2) 0.5072(2) 0.0477(9) Uani 1 1 d . . . C25 C 0.3713(2) 0.1252(2) 0.5097(2) 0.0479(9) Uani 1 1 d . . . H25 H 0.4061 0.1000 0.5520 0.057 Uiso 1 1 calc R . . C26 C 0.4240(2) 0.16712(18) 0.45312(18) 0.0387(8) Uani 1 1 d . . . C27 C 0.2037(2) 0.2514(2) 0.3330(2) 0.0452(8) Uani 1 1 d . . . H27 H 0.2477 0.2805 0.2969 0.054 Uiso 1 1 calc R . . C28 C 0.1363(3) 0.2066(2) 0.2758(2) 0.0642(11) Uani 1 1 d . . . H28A H 0.1755 0.1770 0.2383 0.096 Uiso 1 1 calc R . . H28B H 0.0950 0.2393 0.2431 0.096 Uiso 1 1 calc R . . H28C H 0.0955 0.1749 0.3097 0.096 Uiso 1 1 calc R . . C29 C 0.1437(3) 0.3051(2) 0.3859(2) 0.0634(11) Uani 1 1 d . . . H29A H 0.0988 0.2779 0.4211 0.095 Uiso 1 1 calc R . . H29B H 0.1067 0.3374 0.3490 0.095 Uiso 1 1 calc R . . H29C H 0.1875 0.3339 0.4211 0.095 Uiso 1 1 calc R . . C30 C 0.2168(3) 0.0674(2) 0.5663(2) 0.0601(11) Uani 1 1 d . . . H30 H 0.2668 0.0429 0.6019 0.072 Uiso 1 1 calc R . . C31 C 0.1484(4) 0.1083(3) 0.6239(3) 0.107(2) Uani 1 1 d . . . H31A H 0.0983 0.1329 0.5907 0.161 Uiso 1 1 calc R . . H31B H 0.1853 0.1442 0.6560 0.161 Uiso 1 1 calc R . . H31C H 0.1177 0.0739 0.6619 0.161 Uiso 1 1 calc R . . C32 C 0.1623(4) 0.0087(3) 0.5187(3) 0.0950(16) Uani 1 1 d . . . H32A H 0.1368 -0.0270 0.5579 0.142 Uiso 1 1 calc R . . H32B H 0.2066 -0.0153 0.4801 0.142 Uiso 1 1 calc R . . H32C H 0.1085 0.0306 0.4873 0.142 Uiso 1 1 calc R . . C33 C 0.5339(2) 0.1756(2) 0.4694(2) 0.0466(9) Uani 1 1 d . . . H33 H 0.5598 0.2092 0.4261 0.056 Uiso 1 1 calc R . . C34 C 0.5537(3) 0.2105(3) 0.5553(2) 0.0642(11) Uani 1 1 d . . . H34A H 0.5283 0.1790 0.5990 0.096 Uiso 1 1 calc R . . H34B H 0.5217 0.2579 0.5578 0.096 Uiso 1 1 calc R . . H34C H 0.6238 0.2168 0.5634 0.096 Uiso 1 1 calc R . . C35 C 0.5882(3) 0.1030(2) 0.4613(3) 0.0680(12) Uani 1 1 d . . . H35A H 0.5675 0.0700 0.5055 0.102 Uiso 1 1 calc R . . H35B H 0.6582 0.1115 0.4664 0.102 Uiso 1 1 calc R . . H35C H 0.5736 0.0813 0.4070 0.102 Uiso 1 1 calc R . . B1 B 0.3716(3) 0.1796(2) 0.1395(2) 0.0393(9) Uani 1 1 d . . . C41 C 0.4145(2) 0.10091(19) 0.1600(2) 0.0429(8) Uani 1 1 d . . . F42 F 0.31274(17) 0.07690(12) 0.27592(13) 0.0637(6) Uani 1 1 d . . . C42 C 0.3884(3) 0.0570(2) 0.2267(2) 0.0502(9) Uani 1 1 d . . . C43 C 0.4362(3) -0.0073(2) 0.2478(3) 0.0666(12) Uani 1 1 d . . . F43 F 0.4056(2) -0.04718(14) 0.31410(18) 0.1030(10) Uani 1 1 d . . . F44 F 0.5596(2) -0.09317(15) 0.2210(2) 0.1176(11) Uani 1 1 d . . . C44 C 0.5131(4) -0.0307(2) 0.1999(4) 0.0780(14) Uani 1 1 d . . . F45 F 0.61615(19) -0.01309(16) 0.0850(2) 0.1075(10) Uani 1 1 d . . . C45 C 0.5400(3) 0.0092(3) 0.1318(3) 0.0719(12) Uani 1 1 d . . . F46 F 0.52403(16) 0.11067(13) 0.04630(15) 0.0744(7) Uani 1 1 d . . . C46 C 0.4916(3) 0.0728(2) 0.1132(2) 0.0557(10) Uani 1 1 d . . . C51 C 0.3358(2) 0.19051(19) 0.04423(19) 0.0405(8) Uani 1 1 d . . . F52 F 0.21698(18) 0.09872(14) 0.05663(16) 0.0817(8) Uani 1 1 d . . . C52 C 0.2641(3) 0.1472(2) 0.0084(2) 0.0521(9) Uani 1 1 d . . . F53 F 0.1697(2) 0.10372(17) -0.10630(18) 0.1052(10) Uani 1 1 d . . . C53 C 0.2385(3) 0.1488(2) -0.0755(3) 0.0626(11) Uani 1 1 d . . . F54 F 0.2648(2) 0.19732(18) -0.20976(14) 0.1076(11) Uani 1 1 d . . . C54 C 0.2860(3) 0.1969(3) -0.1270(2) 0.0644(12) Uani 1 1 d . . . F55 F 0.4039(2) 0.28871(18) -0.14585(15) 0.1023(10) Uani 1 1 d . . . C55 C 0.3561(3) 0.2421(3) -0.0952(2) 0.0625(11) Uani 1 1 d . . . F56 F 0.45243(16) 0.28267(13) 0.01581(13) 0.0690(7) Uani 1 1 d . . . C56 C 0.3799(2) 0.2387(2) -0.0111(2) 0.0489(9) 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 0.0373(4) 0.0359(5) 0.0318(4) 0.0030(4) 0.0058(3) 0.0041(4) C11 0.0418(18) 0.045(2) 0.0358(17) 0.0049(16) 0.0073(14) 0.0051(16) C2 0.0379(16) 0.044(2) 0.0328(17) 0.0035(16) 0.0031(13) 0.0053(15) C3 0.0453(18) 0.049(2) 0.0322(17) 0.0087(17) 0.0059(14) 0.0102(16) C4 0.0487(19) 0.042(2) 0.0361(18) 0.0029(17) 0.0085(15) 0.0054(16) C5 0.0427(18) 0.0399(19) 0.0345(17) 0.0024(15) 0.0088(14) -0.0012(15) C6 0.055(2) 0.040(2) 0.0398(19) -0.0016(16) 0.0064(15) -0.0004(16) C7 0.073(3) 0.042(2) 0.051(2) -0.0049(19) 0.0073(19) 0.0028(19) C8 0.083(3) 0.040(2) 0.064(3) 0.001(2) 0.011(2) 0.013(2) C9 0.069(2) 0.043(2) 0.054(2) 0.0082(19) 0.0052(19) 0.0063(19) C12 0.0453(19) 0.048(2) 0.0390(18) 0.0037(17) 0.0067(15) 0.0031(16) C13 0.027(9) 0.043(13) 0.036(11) -0.001(11) -0.006(7) 0.000(9) C14 0.043(10) 0.048(15) 0.075(13) 0.014(11) 0.015(10) -0.008(9) C15 0.051(11) 0.071(14) 0.107(14) 0.008(13) 0.031(12) 0.017(11) C16 0.063(8) 0.064(8) 0.060(8) 0.004(6) 0.014(6) 0.014(6) C17 0.064(8) 0.062(8) 0.055(8) 0.002(7) 0.023(6) 0.005(7) C18 0.050(10) 0.099(14) 0.027(9) -0.007(9) 0.019(9) 0.005(10) C13A 0.042(7) 0.046(6) 0.042(6) -0.007(5) 0.011(6) 0.003(6) C14A 0.055(7) 0.051(9) 0.070(5) 0.014(5) 0.024(5) 0.017(8) C15A 0.069(7) 0.071(7) 0.101(6) 0.026(5) 0.032(5) 0.031(6) C16A 0.055(4) 0.065(4) 0.075(5) 0.003(4) 0.022(3) 0.010(3) C17A 0.067(4) 0.075(5) 0.051(4) -0.013(3) 0.024(3) -0.001(4) C18A 0.056(5) 0.079(6) 0.042(5) 0.004(5) 0.001(4) 0.014(5) C21 0.0382(16) 0.0343(18) 0.0295(16) 0.0050(14) 0.0061(13) 0.0026(14) C22 0.0414(17) 0.043(2) 0.0331(17) 0.0022(16) 0.0031(14) 0.0047(15) C23 0.0395(18) 0.054(2) 0.0425(19) 0.0084(17) 0.0060(15) -0.0010(16) C24 0.051(2) 0.052(2) 0.0408(19) 0.0108(17) 0.0046(16) -0.0026(17) C25 0.053(2) 0.052(2) 0.0389(19) 0.0157(18) -0.0034(16) 0.0045(17) C26 0.0456(18) 0.041(2) 0.0301(17) 0.0015(15) 0.0031(14) 0.0018(15) C27 0.0399(17) 0.056(2) 0.0397(18) 0.0107(18) 0.0082(14) 0.0101(17) C28 0.050(2) 0.092(3) 0.050(2) 0.007(2) -0.0068(17) 0.004(2) C29 0.053(2) 0.071(3) 0.066(3) 0.010(2) 0.0159(19) 0.020(2) C30 0.058(2) 0.070(3) 0.053(2) 0.025(2) 0.0060(18) -0.010(2) C31 0.150(5) 0.096(4) 0.077(3) 0.016(3) 0.061(3) -0.019(4) C32 0.120(4) 0.075(4) 0.090(4) 0.021(3) 0.008(3) -0.036(3) C33 0.0413(18) 0.061(2) 0.0373(18) 0.0096(18) 0.0011(14) 0.0025(17) C34 0.055(2) 0.092(3) 0.045(2) 0.005(2) -0.0074(17) -0.008(2) C35 0.056(2) 0.080(3) 0.068(3) 0.017(2) 0.003(2) 0.026(2) B1 0.0386(19) 0.042(2) 0.037(2) 0.0033(18) 0.0066(16) -0.0015(17) C41 0.0451(19) 0.038(2) 0.0455(19) -0.0035(17) -0.0041(15) -0.0045(16) F42 0.0887(16) 0.0502(13) 0.0524(12) 0.0052(11) 0.0152(11) -0.0057(12) C42 0.059(2) 0.041(2) 0.050(2) -0.0030(18) -0.0032(18) -0.0064(18) C43 0.092(3) 0.040(2) 0.068(3) 0.011(2) -0.022(2) -0.007(2) F43 0.155(3) 0.0575(17) 0.096(2) 0.0336(16) -0.0095(18) 0.0001(17) F44 0.121(2) 0.0596(18) 0.171(3) 0.0084(19) -0.033(2) 0.0334(17) C44 0.075(3) 0.044(3) 0.114(4) -0.008(3) -0.023(3) 0.015(2) F45 0.0782(17) 0.083(2) 0.162(3) -0.024(2) 0.0186(18) 0.0294(15) C45 0.057(2) 0.057(3) 0.101(4) -0.013(3) 0.000(2) 0.010(2) F46 0.0682(14) 0.0756(17) 0.0798(16) -0.0012(14) 0.0264(12) 0.0072(12) C46 0.056(2) 0.047(2) 0.064(3) -0.002(2) 0.0000(19) -0.0004(19) C51 0.0418(18) 0.043(2) 0.0370(18) -0.0020(16) 0.0041(14) 0.0032(15) F52 0.0821(16) 0.0742(17) 0.0887(18) 0.0127(15) -0.0110(13) -0.0356(14) C52 0.054(2) 0.047(2) 0.055(2) 0.0022(19) -0.0014(18) 0.0000(18) F53 0.101(2) 0.104(2) 0.109(2) -0.0248(18) -0.0552(17) -0.0074(18) C53 0.062(2) 0.062(3) 0.064(3) -0.015(2) -0.025(2) 0.009(2) F54 0.129(2) 0.146(3) 0.0461(14) -0.0048(16) -0.0291(14) 0.050(2) C54 0.074(3) 0.080(3) 0.039(2) -0.007(2) -0.013(2) 0.029(3) F55 0.1010(19) 0.142(3) 0.0641(16) 0.0497(17) 0.0172(14) 0.0035(19) C55 0.063(2) 0.083(3) 0.042(2) 0.018(2) 0.0095(18) 0.017(2) F56 0.0655(14) 0.0819(17) 0.0598(13) 0.0120(13) 0.0082(11) -0.0260(13) C56 0.0450(19) 0.058(2) 0.044(2) 0.0026(18) 0.0043(15) -0.0003(18) _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 1.741(3) . ? P1 C2 1.765(3) . ? P1 C5 1.827(3) . ? P1 C21 1.830(3) . ? C11 C12 1.191(4) . ? C2 B1 1.452(5) . ? C2 C3 1.469(5) . ? C3 C4 1.332(5) . ? C3 H3 0.9400 . ? C4 C9 1.495(5) . ? C4 C5 1.522(4) . ? C5 C6 1.533(4) . ? C5 H5 0.9900 . ? C6 C7 1.517(5) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C7 C8 1.517(5) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C8 C9 1.531(5) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C12 C13A 1.438(7) . ? C12 C13 1.442(16) . ? C13 C14 1.370(19) . ? C13 C18 1.483(14) . ? C14 C15 1.502(15) . ? C14 H14 0.9400 . ? C15 C16 1.535(16) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C16 C17 1.529(14) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C17 C18 1.547(15) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C13A C14A 1.364(12) . ? C13A C18A 1.474(8) . ? C14A C15A 1.500(8) . ? C14A H14A 0.9400 . ? C15A C16A 1.536(12) . ? C15A H15C 0.9800 . ? C15A H15D 0.9800 . ? C16A C17A 1.529(8) . ? C16A H16C 0.9800 . ? C16A H16D 0.9800 . ? C17A C18A 1.531(10) . ? C17A H17C 0.9800 . ? C17A H17D 0.9800 . ? C18A H18C 0.9800 . ? C18A H18D 0.9800 . ? C21 C26 1.415(4) . ? C21 C22 1.419(4) . ? C22 C23 1.388(4) . ? C22 C27 1.518(4) . ? C23 C24 1.379(5) . ? C23 H23 0.9400 . ? C24 C25 1.382(5) . ? C24 C30 1.520(5) . ? C25 C26 1.389(4) . ? C25 H25 0.9400 . ? C26 C33 1.526(4) . ? C27 C28 1.526(5) . ? C27 C29 1.535(5) . ? C27 H27 0.9900 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 H28C 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ? C30 C32 1.505(6) . ? C30 C31 1.513(6) . ? C30 H30 0.9900 . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C31 H31C 0.9700 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C32 H32C 0.9700 . ? C33 C35 1.525(5) . ? C33 C34 1.530(5) . ? C33 H33 0.9900 . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C34 H34C 0.9700 . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C35 H35C 0.9700 . ? B1 C41 1.584(5) . ? B1 C51 1.602(5) . ? C41 C42 1.380(5) . ? C41 C46 1.393(5) . ? F42 C42 1.352(4) . ? C42 C43 1.382(5) . ? C43 F43 1.352(5) . ? C43 C44 1.372(6) . ? F44 C44 1.346(5) . ? C44 C45 1.360(6) . ? F45 C45 1.348(5) . ? C45 C46 1.367(6) . ? F46 C46 1.348(4) . ? C51 C52 1.377(5) . ? C51 C56 1.387(5) . ? F52 C52 1.341(4) . ? C52 C53 1.378(5) . ? F53 C53 1.338(4) . ? C53 C54 1.368(6) . ? F54 C54 1.346(4) . ? C54 C55 1.357(6) . ? F55 C55 1.346(4) . ? C55 C56 1.377(5) . ? F56 C56 1.341(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 P1 C2 106.48(15) . . ? C11 P1 C5 109.40(16) . . ? C2 P1 C5 98.00(15) . . ? C11 P1 C21 109.59(14) . . ? C2 P1 C21 120.02(14) . . ? C5 P1 C21 112.52(14) . . ? C12 C11 P1 164.9(3) . . ? B1 C2 C3 129.6(3) . . ? B1 C2 P1 125.4(3) . . ? C3 C2 P1 103.3(2) . . ? C4 C3 C2 120.3(3) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C9 129.2(3) . . ? C3 C4 C5 114.7(3) . . ? C9 C4 C5 116.1(3) . . ? C4 C5 C6 112.5(3) . . ? C4 C5 P1 102.3(2) . . ? C6 C5 P1 116.1(2) . . ? C4 C5 H5 108.5 . . ? C6 C5 H5 108.5 . . ? P1 C5 H5 108.5 . . ? C7 C6 C5 110.3(3) . . ? C7 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? C7 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C8 C7 C6 111.4(3) . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7B 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C7 C8 C9 111.8(3) . . ? C7 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? C4 C9 C8 111.5(3) . . ? C4 C9 H9A 109.3 . . ? C8 C9 H9A 109.3 . . ? C4 C9 H9B 109.3 . . ? C8 C9 H9B 109.3 . . ? H9A C9 H9B 108.0 . . ? C11 C12 C13A 175.5(11) . . ? C11 C12 C13 172(3) . . ? C13A C12 C13 9(5) . . ? C14 C13 C12 119(3) . . ? C14 C13 C18 121.4(19) . . ? C12 C13 C18 115.7(17) . . ? C13 C14 C15 121.6(19) . . ? C13 C14 H14 119.2 . . ? C15 C14 H14 119.2 . . ? C14 C15 C16 112.3(18) . . ? C14 C15 H15A 109.1 . . ? C16 C15 H15A 109.1 . . ? C14 C15 H15B 109.1 . . ? C16 C15 H15B 109.1 . . ? H15A C15 H15B 107.9 . . ? C17 C16 C15 106.3(19) . . ? C17 C16 H16A 110.5 . . ? C15 C16 H16A 110.5 . . ? C17 C16 H16B 110.5 . . ? C15 C16 H16B 110.5 . . ? H16A C16 H16B 108.7 . . ? C16 C17 C18 105.2(18) . . ? C16 C17 H17A 110.7 . . ? C18 C17 H17A 110.7 . . ? C16 C17 H17B 110.7 . . ? C18 C17 H17B 110.7 . . ? H17A C17 H17B 108.8 . . ? C13 C18 C17 111(2) . . ? C13 C18 H18A 109.4 . . ? C17 C18 H18A 109.4 . . ? C13 C18 H18B 109.4 . . ? C17 C18 H18B 109.4 . . ? H18A C18 H18B 108.0 . . ? C14A C13A C12 120.5(9) . . ? C14A C13A C18A 123.4(7) . . ? C12 C13A C18A 115.5(7) . . ? C13A C14A C15A 120.3(10) . . ? C13A C14A H14A 119.8 . . ? C15A C14A H14A 119.8 . . ? C14A C15A C16A 113.0(10) . . ? C14A C15A H15C 109.0 . . ? C16A C15A H15C 109.0 . . ? C14A C15A H15D 109.0 . . ? C16A C15A H15D 109.0 . . ? H15C C15A H15D 107.8 . . ? C17A C16A C15A 108.2(9) . . ? C17A C16A H16C 110.1 . . ? C15A C16A H16C 110.1 . . ? C17A C16A H16D 110.1 . . ? C15A C16A H16D 110.1 . . ? H16C C16A H16D 108.4 . . ? C16A C17A C18A 108.1(8) . . ? C16A C17A H17C 110.1 . . ? C18A C17A H17C 110.1 . . ? C16A C17A H17D 110.1 . . ? C18A C17A H17D 110.1 . . ? H17C C17A H17D 108.4 . . ? C13A C18A C17A 114.2(8) . . ? C13A C18A H18C 108.7 . . ? C17A C18A H18C 108.7 . . ? C13A C18A H18D 108.7 . . ? C17A C18A H18D 108.7 . . ? H18C C18A H18D 107.6 . . ? C26 C21 C22 119.5(3) . . ? C26 C21 P1 121.5(2) . . ? C22 C21 P1 118.8(2) . . ? C23 C22 C21 118.2(3) . . ? C23 C22 C27 117.6(3) . . ? C21 C22 C27 124.2(3) . . ? C24 C23 C22 123.1(3) . . ? C24 C23 H23 118.5 . . ? C22 C23 H23 118.5 . . ? C23 C24 C25 117.1(3) . . ? C23 C24 C30 121.5(3) . . ? C25 C24 C30 121.4(3) . . ? C24 C25 C26 123.4(3) . . ? C24 C25 H25 118.3 . . ? C26 C25 H25 118.3 . . ? C25 C26 C21 117.9(3) . . ? C25 C26 C33 117.4(3) . . ? C21 C26 C33 124.6(3) . . ? C22 C27 C28 112.6(3) . . ? C22 C27 C29 110.2(3) . . ? C28 C27 C29 110.4(3) . . ? C22 C27 H27 107.8 . . ? C28 C27 H27 107.8 . . ? C29 C27 H27 107.8 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C32 C30 C31 110.6(4) . . ? C32 C30 C24 111.5(3) . . ? C31 C30 C24 112.1(4) . . ? C32 C30 H30 107.5 . . ? C31 C30 H30 107.5 . . ? C24 C30 H30 107.5 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C30 C32 H32A 109.5 . . ? C30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C35 C33 C26 112.0(3) . . ? C35 C33 C34 110.8(3) . . ? C26 C33 C34 111.0(3) . . ? C35 C33 H33 107.6 . . ? C26 C33 H33 107.6 . . ? C34 C33 H33 107.6 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C2 B1 C41 124.2(3) . . ? C2 B1 C51 120.8(3) . . ? C41 B1 C51 114.6(3) . . ? C42 C41 C46 113.6(3) . . ? C42 C41 B1 126.0(3) . . ? C46 C41 B1 120.2(3) . . ? F42 C42 C41 119.6(3) . . ? F42 C42 C43 116.7(3) . . ? C41 C42 C43 123.7(4) . . ? F43 C43 C44 120.7(4) . . ? F43 C43 C42 119.9(4) . . ? C44 C43 C42 119.4(4) . . ? F44 C44 C45 121.5(5) . . ? F44 C44 C43 119.1(5) . . ? C45 C44 C43 119.4(4) . . ? F45 C45 C44 119.7(4) . . ? F45 C45 C46 120.7(5) . . ? C44 C45 C46 119.6(4) . . ? F46 C46 C45 116.4(4) . . ? F46 C46 C41 119.4(3) . . ? C45 C46 C41 124.2(4) . . ? C52 C51 C56 114.4(3) . . ? C52 C51 B1 122.0(3) . . ? C56 C51 B1 123.4(3) . . ? F52 C52 C51 119.0(3) . . ? F52 C52 C53 116.8(4) . . ? C51 C52 C53 124.2(4) . . ? F53 C53 C54 120.7(4) . . ? F53 C53 C52 120.8(4) . . ? C54 C53 C52 118.5(4) . . ? F54 C54 C55 120.3(4) . . ? F54 C54 C53 119.5(4) . . ? C55 C54 C53 120.2(4) . . ? F55 C55 C54 120.4(4) . . ? F55 C55 C56 120.0(4) . . ? C54 C55 C56 119.6(4) . . ? F56 C56 C55 116.7(3) . . ? F56 C56 C51 120.1(3) . . ? C55 C56 C51 123.1(4) . . ? 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 P1 C11 C12 27.5(13) . . . . ? C5 P1 C11 C12 -77.4(13) . . . . ? C21 P1 C11 C12 158.8(12) . . . . ? C11 P1 C2 B1 42.5(3) . . . . ? C5 P1 C2 B1 155.5(3) . . . . ? C21 P1 C2 B1 -82.6(3) . . . . ? C11 P1 C2 C3 -123.8(2) . . . . ? C5 P1 C2 C3 -10.7(2) . . . . ? C21 P1 C2 C3 111.1(2) . . . . ? B1 C2 C3 C4 -157.6(3) . . . . ? P1 C2 C3 C4 7.8(4) . . . . ? C2 C3 C4 C9 179.7(3) . . . . ? C2 C3 C4 C5 0.4(4) . . . . ? C3 C4 C5 C6 -133.5(3) . . . . ? C9 C4 C5 C6 47.2(4) . . . . ? C3 C4 C5 P1 -8.1(3) . . . . ? C9 C4 C5 P1 172.5(2) . . . . ? C11 P1 C5 C4 121.6(2) . . . . ? C2 P1 C5 C4 11.0(2) . . . . ? C21 P1 C5 C4 -116.3(2) . . . . ? C11 P1 C5 C6 -115.5(3) . . . . ? C2 P1 C5 C6 133.8(2) . . . . ? C21 P1 C5 C6 6.6(3) . . . . ? C4 C5 C6 C7 -51.0(4) . . . . ? P1 C5 C6 C7 -168.4(2) . . . . ? C5 C6 C7 C8 57.5(4) . . . . ? C6 C7 C8 C9 -58.4(4) . . . . ? C3 C4 C9 C8 134.0(4) . . . . ? C5 C4 C9 C8 -46.7(4) . . . . ? C7 C8 C9 C4 51.6(4) . . . . ? P1 C11 C12 C13A 55(16) . . . . ? P1 C11 C12 C13 -36(18) . . . . ? C11 C12 C13 C14 -148(13) . . . . ? C13A C12 C13 C14 62(9) . . . . ? C11 C12 C13 C18 53(23) . . . . ? C13A C12 C13 C18 -97(14) . . . . ? C12 C13 C14 C15 -173(6) . . . . ? C18 C13 C14 C15 -15(11) . . . . ? C13 C14 C15 C16 -4(9) . . . . ? C14 C15 C16 C17 47(5) . . . . ? C15 C16 C17 C18 -73(3) . . . . ? C14 C13 C18 C17 -12(9) . . . . ? C12 C13 C18 C17 146(5) . . . . ? C16 C17 C18 C13 55(4) . . . . ? C11 C12 C13A C14A 149(13) . . . . ? C13 C12 C13A C14A -91(13) . . . . ? C11 C12 C13A C18A -40(18) . . . . ? C13 C12 C13A C18A 80(10) . . . . ? C12 C13A C14A C15A 179(2) . . . . ? C18A C13A C14A C15A 8(5) . . . . ? C13A C14A C15A C16A 14(4) . . . . ? C14A C15A C16A C17A -51(2) . . . . ? C15A C16A C17A C18A 65.2(15) . . . . ? C14A C13A C18A C17A 8(4) . . . . ? C12 C13A C18A C17A -163.4(19) . . . . ? C16A C17A C18A C13A -44(2) . . . . ? C11 P1 C21 C26 23.0(3) . . . . ? C2 P1 C21 C26 146.6(3) . . . . ? C5 P1 C21 C26 -99.0(3) . . . . ? C11 P1 C21 C22 -151.5(3) . . . . ? C2 P1 C21 C22 -27.9(3) . . . . ? C5 P1 C21 C22 86.5(3) . . . . ? C26 C21 C22 C23 -8.6(5) . . . . ? P1 C21 C22 C23 166.0(3) . . . . ? C26 C21 C22 C27 168.4(3) . . . . ? P1 C21 C22 C27 -16.9(4) . . . . ? C21 C22 C23 C24 1.2(5) . . . . ? C27 C22 C23 C24 -176.0(3) . . . . ? C22 C23 C24 C25 5.5(5) . . . . ? C22 C23 C24 C30 -174.6(3) . . . . ? C23 C24 C25 C26 -5.1(6) . . . . ? C30 C24 C25 C26 175.0(4) . . . . ? C24 C25 C26 C21 -2.1(5) . . . . ? C24 C25 C26 C33 173.6(3) . . . . ? C22 C21 C26 C25 9.0(5) . . . . ? P1 C21 C26 C25 -165.5(3) . . . . ? C22 C21 C26 C33 -166.4(3) . . . . ? P1 C21 C26 C33 19.1(4) . . . . ? C23 C22 C27 C28 -64.5(4) . . . . ? C21 C22 C27 C28 118.5(4) . . . . ? C23 C22 C27 C29 59.2(4) . . . . ? C21 C22 C27 C29 -117.8(4) . . . . ? C23 C24 C30 C32 62.2(5) . . . . ? C25 C24 C30 C32 -117.9(4) . . . . ? C23 C24 C30 C31 -62.4(5) . . . . ? C25 C24 C30 C31 117.5(4) . . . . ? C25 C26 C33 C35 65.5(4) . . . . ? C21 C26 C33 C35 -119.1(4) . . . . ? C25 C26 C33 C34 -58.9(4) . . . . ? C21 C26 C33 C34 116.5(4) . . . . ? C3 C2 B1 C41 167.4(3) . . . . ? P1 C2 B1 C41 4.8(5) . . . . ? C3 C2 B1 C51 -4.6(5) . . . . ? P1 C2 B1 C51 -167.2(2) . . . . ? C2 B1 C41 C42 57.1(5) . . . . ? C51 B1 C41 C42 -130.5(3) . . . . ? C2 B1 C41 C46 -117.1(4) . . . . ? C51 B1 C41 C46 55.3(4) . . . . ? C46 C41 C42 F42 -178.1(3) . . . . ? B1 C41 C42 F42 7.4(5) . . . . ? C46 C41 C42 C43 2.6(5) . . . . ? B1 C41 C42 C43 -171.9(3) . . . . ? F42 C42 C43 F43 0.9(5) . . . . ? C41 C42 C43 F43 -179.8(3) . . . . ? F42 C42 C43 C44 179.5(4) . . . . ? C41 C42 C43 C44 -1.2(6) . . . . ? F43 C43 C44 F44 -1.7(6) . . . . ? C42 C43 C44 F44 179.7(4) . . . . ? F43 C43 C44 C45 177.6(4) . . . . ? C42 C43 C44 C45 -1.0(7) . . . . ? F44 C44 C45 F45 -1.4(7) . . . . ? C43 C44 C45 F45 179.3(4) . . . . ? F44 C44 C45 C46 -179.2(4) . . . . ? C43 C44 C45 C46 1.5(7) . . . . ? F45 C45 C46 F46 0.2(6) . . . . ? C44 C45 C46 F46 178.0(4) . . . . ? F45 C45 C46 C41 -177.7(4) . . . . ? C44 C45 C46 C41 0.1(7) . . . . ? C42 C41 C46 F46 -179.9(3) . . . . ? B1 C41 C46 F46 -5.1(5) . . . . ? C42 C41 C46 C45 -2.1(5) . . . . ? B1 C41 C46 C45 172.8(4) . . . . ? C2 B1 C51 C52 -128.2(4) . . . . ? C41 B1 C51 C52 59.1(4) . . . . ? C2 B1 C51 C56 58.2(4) . . . . ? C41 B1 C51 C56 -114.5(4) . . . . ? C56 C51 C52 F52 179.9(3) . . . . ? B1 C51 C52 F52 5.8(5) . . . . ? C56 C51 C52 C53 1.8(5) . . . . ? B1 C51 C52 C53 -172.3(3) . . . . ? F52 C52 C53 F53 0.1(6) . . . . ? C51 C52 C53 F53 178.3(3) . . . . ? F52 C52 C53 C54 -179.0(3) . . . . ? C51 C52 C53 C54 -0.9(6) . . . . ? F53 C53 C54 F54 -1.7(6) . . . . ? C52 C53 C54 F54 177.5(3) . . . . ? F53 C53 C54 C55 -179.6(4) . . . . ? C52 C53 C54 C55 -0.5(6) . . . . ? F54 C54 C55 F55 1.2(6) . . . . ? C53 C54 C55 F55 179.1(4) . . . . ? F54 C54 C55 C56 -177.2(3) . . . . ? C53 C54 C55 C56 0.7(6) . . . . ? F55 C55 C56 F56 -1.0(5) . . . . ? C54 C55 C56 F56 177.4(3) . . . . ? F55 C55 C56 C51 -178.1(3) . . . . ? C54 C55 C56 C51 0.4(6) . . . . ? C52 C51 C56 F56 -178.5(3) . . . . ? B1 C51 C56 F56 -4.4(5) . . . . ? C52 C51 C56 C55 -1.6(5) . . . . ? B1 C51 C56 C55 172.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.284 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.046 _database_code_depnum_ccdc_archive 'CCDC 956699' ####################################################################### # # 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_erk6308 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H23 Cl2 P' _chemical_formula_weight 305.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 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 11.1581(2) _cell_length_b 14.1182(3) _cell_length_c 11.5860(2) _cell_angle_alpha 90.00 _cell_angle_beta 117.115(1) _cell_angle_gamma 90.00 _cell_volume 1624.57(5) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3823 _cell_measurement_theta_min 4.08 _cell_measurement_theta_max 28.28 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.481 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8692 _exptl_absorpt_correction_T_max 0.9227 _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 12599 _diffrn_reflns_av_R_equivalents 0.027 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.35 _diffrn_reflns_theta_max 28.27 _reflns_number_total 3946 _reflns_number_gt 3520 _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^)+(0.0362P)^2^+0.7004P] 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 3946 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0403 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0930 _refine_ls_wR_factor_gt 0.0884 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.66393(4) 0.06216(3) 0.45278(4) 0.03669(11) Uani 1 1 d . . . Cl1 Cl 0.67438(5) 0.01869(3) 0.28574(4) 0.04860(12) Uani 1 1 d . . . Cl2 Cl 0.84708(5) 0.01345(3) 0.59595(4) 0.05277(13) Uani 1 1 d . . . C1 C 0.69250(13) 0.18933(9) 0.45446(12) 0.0277(3) Uani 1 1 d . . . C2 C 0.80285(13) 0.23445(9) 0.44780(12) 0.0279(3) Uani 1 1 d . . . C3 C 0.80972(13) 0.33262(10) 0.45364(13) 0.0306(3) Uani 1 1 d . . . H3 H 0.8824 0.3628 0.4487 0.037 Uiso 1 1 calc R . . C4 C 0.71343(13) 0.38826(9) 0.46649(13) 0.0296(3) Uani 1 1 d . . . C5 C 0.60572(13) 0.34313(9) 0.47126(13) 0.0302(3) Uani 1 1 d . . . H5 H 0.5397 0.3800 0.4791 0.036 Uiso 1 1 calc R . . C6 C 0.59176(13) 0.24475(9) 0.46480(12) 0.0280(3) Uani 1 1 d . . . C7 C 0.91682(13) 0.18294(10) 0.43514(13) 0.0316(3) Uani 1 1 d . . . H7 H 0.8984 0.1141 0.4306 0.038 Uiso 1 1 calc R . . C8 C 1.05197(16) 0.20149(13) 0.55438(17) 0.0447(4) Uani 1 1 d . . . H8A H 1.0720 0.2687 0.5608 0.067 Uiso 1 1 calc R . . H8B H 1.1226 0.1668 0.5459 0.067 Uiso 1 1 calc R . . H8C H 1.0469 0.1807 0.6318 0.067 Uiso 1 1 calc R . . C9 C 0.92221(17) 0.21220(12) 0.31018(16) 0.0415(3) Uani 1 1 d . . . H9A H 0.9429 0.2792 0.3138 0.062 Uiso 1 1 calc R . . H9B H 0.8357 0.1999 0.2363 0.062 Uiso 1 1 calc R . . H9C H 0.9915 0.1760 0.3014 0.062 Uiso 1 1 calc R . . C10 C 0.72665(15) 0.49542(10) 0.47477(16) 0.0356(3) Uani 1 1 d . . . H10 H 0.6511 0.5207 0.4881 0.043 Uiso 1 1 calc R . . C11 C 0.7157(2) 0.53760(13) 0.34920(19) 0.0538(4) Uani 1 1 d . . . H11A H 0.7924 0.5177 0.3370 0.081 Uiso 1 1 calc R . . H11B H 0.7145 0.6062 0.3539 0.081 Uiso 1 1 calc R . . H11C H 0.6333 0.5158 0.2768 0.081 Uiso 1 1 calc R . . C12 C 0.85775(18) 0.52596(12) 0.59038(18) 0.0465(4) Uani 1 1 d . . . H12A H 0.8613 0.5003 0.6695 0.070 Uiso 1 1 calc R . . H12B H 0.8616 0.5946 0.5955 0.070 Uiso 1 1 calc R . . H12C H 0.9337 0.5024 0.5795 0.070 Uiso 1 1 calc R . . C13 C 0.47010(14) 0.20256(10) 0.47401(14) 0.0340(3) Uani 1 1 d . . . H13 H 0.4628 0.1353 0.4475 0.041 Uiso 1 1 calc R . . C14 C 0.4914(2) 0.2050(2) 0.6127(2) 0.0733(7) Uani 1 1 d . . . H14A H 0.5061 0.2699 0.6438 0.110 Uiso 1 1 calc R . . H14B H 0.5693 0.1669 0.6668 0.110 Uiso 1 1 calc R . . H14C H 0.4123 0.1798 0.6165 0.110 Uiso 1 1 calc R . . C15 C 0.33884(16) 0.25144(14) 0.3831(2) 0.0535(4) Uani 1 1 d . . . H15A H 0.2633 0.2155 0.3800 0.080 Uiso 1 1 calc R . . H15B H 0.3323 0.2551 0.2968 0.080 Uiso 1 1 calc R . . H15C H 0.3374 0.3149 0.4147 0.080 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 0.0427(2) 0.02536(18) 0.0493(2) -0.00061(15) 0.02732(18) -0.00021(15) Cl1 0.0552(2) 0.0444(2) 0.0491(2) -0.01829(17) 0.02625(19) -0.00817(18) Cl2 0.0635(3) 0.0448(2) 0.0509(2) 0.01760(18) 0.0268(2) 0.02078(19) C1 0.0301(6) 0.0247(6) 0.0278(6) -0.0003(5) 0.0127(5) 0.0011(5) C2 0.0261(6) 0.0296(6) 0.0270(6) -0.0011(5) 0.0113(5) 0.0011(5) C3 0.0284(6) 0.0295(6) 0.0363(7) -0.0013(5) 0.0169(5) -0.0015(5) C4 0.0296(6) 0.0261(6) 0.0327(6) -0.0011(5) 0.0138(5) -0.0002(5) C5 0.0287(6) 0.0283(6) 0.0349(7) -0.0015(5) 0.0158(5) 0.0019(5) C6 0.0261(6) 0.0290(6) 0.0285(6) -0.0012(5) 0.0121(5) -0.0007(5) C7 0.0287(6) 0.0313(7) 0.0366(7) -0.0023(5) 0.0166(5) 0.0028(5) C8 0.0311(7) 0.0498(9) 0.0468(9) -0.0062(7) 0.0122(6) 0.0066(7) C9 0.0447(8) 0.0440(8) 0.0443(8) -0.0030(7) 0.0275(7) 0.0015(7) C10 0.0349(7) 0.0256(6) 0.0503(8) -0.0006(6) 0.0229(7) 0.0004(5) C11 0.0601(11) 0.0388(9) 0.0609(11) 0.0139(8) 0.0261(9) 0.0036(8) C12 0.0456(9) 0.0373(8) 0.0568(10) -0.0104(7) 0.0233(8) -0.0070(7) C13 0.0310(7) 0.0307(7) 0.0441(8) -0.0034(6) 0.0204(6) -0.0036(5) C14 0.0648(13) 0.114(2) 0.0492(10) 0.0042(11) 0.0333(10) -0.0315(13) C15 0.0299(8) 0.0531(10) 0.0728(12) 0.0013(9) 0.0192(8) -0.0015(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 C1 1.8221(14) . ? P1 Cl2 2.0762(6) . ? P1 Cl1 2.0835(6) . ? C1 C6 1.4188(18) . ? C1 C2 1.4193(18) . ? C2 C3 1.3880(19) . ? C2 C7 1.5289(18) . ? C3 C4 1.3926(18) . ? C3 H3 0.9400 . ? C4 C5 1.3835(18) . ? C4 C10 1.5188(19) . ? C5 C6 1.3958(18) . ? C5 H5 0.9400 . ? C6 C13 1.5301(18) . ? C7 C9 1.533(2) . ? C7 C8 1.534(2) . ? C7 H7 0.9900 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 H9C 0.9700 . ? C10 C11 1.525(2) . ? C10 C12 1.528(2) . ? C10 H10 0.9900 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 H11C 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 H12C 0.9700 . ? C13 C14 1.514(2) . ? C13 C15 1.525(2) . ? C13 H13 0.9900 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 H14C 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 H15C 0.9700 . ? 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 Cl2 102.36(5) . . ? C1 P1 Cl1 102.51(5) . . ? Cl2 P1 Cl1 101.14(2) . . ? C6 C1 C2 119.83(12) . . ? C6 C1 P1 113.76(10) . . ? C2 C1 P1 126.41(10) . . ? C3 C2 C1 118.39(12) . . ? C3 C2 C7 116.73(12) . . ? C1 C2 C7 124.88(12) . . ? C2 C3 C4 122.70(12) . . ? C2 C3 H3 118.6 . . ? C4 C3 H3 118.6 . . ? C5 C4 C3 118.11(12) . . ? C5 C4 C10 121.15(12) . . ? C3 C4 C10 120.74(12) . . ? C4 C5 C6 122.27(12) . . ? C4 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C5 C6 C1 118.68(12) . . ? C5 C6 C13 117.68(12) . . ? C1 C6 C13 123.60(12) . . ? C2 C7 C9 110.78(11) . . ? C2 C7 C8 110.59(11) . . ? C9 C7 C8 111.04(13) . . ? C2 C7 H7 108.1 . . ? C9 C7 H7 108.1 . . ? C8 C7 H7 108.1 . . ? 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 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C4 C10 C11 111.44(13) . . ? C4 C10 C12 111.29(13) . . ? C11 C10 C12 110.77(14) . . ? C4 C10 H10 107.7 . . ? C11 C10 H10 107.7 . . ? C12 C10 H10 107.7 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C15 111.05(16) . . ? C14 C13 C6 110.51(13) . . ? C15 C13 C6 112.28(13) . . ? C14 C13 H13 107.6 . . ? C15 C13 H13 107.6 . . ? C6 C13 H13 107.6 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 P1 C1 C6 -128.63(9) . . . . ? Cl1 P1 C1 C6 126.82(9) . . . . ? Cl2 P1 C1 C2 50.76(12) . . . . ? Cl1 P1 C1 C2 -53.79(12) . . . . ? C6 C1 C2 C3 0.96(18) . . . . ? P1 C1 C2 C3 -178.39(10) . . . . ? C6 C1 C2 C7 -179.34(12) . . . . ? P1 C1 C2 C7 1.30(19) . . . . ? C1 C2 C3 C4 0.4(2) . . . . ? C7 C2 C3 C4 -179.34(12) . . . . ? C2 C3 C4 C5 -1.1(2) . . . . ? C2 C3 C4 C10 178.95(13) . . . . ? C3 C4 C5 C6 0.6(2) . . . . ? C10 C4 C5 C6 -179.52(13) . . . . ? C4 C5 C6 C1 0.7(2) . . . . ? C4 C5 C6 C13 178.68(12) . . . . ? C2 C1 C6 C5 -1.50(19) . . . . ? P1 C1 C6 C5 177.93(10) . . . . ? C2 C1 C6 C13 -179.32(12) . . . . ? P1 C1 C6 C13 0.12(17) . . . . ? C3 C2 C7 C9 -60.78(16) . . . . ? C1 C2 C7 C9 119.52(14) . . . . ? C3 C2 C7 C8 62.78(16) . . . . ? C1 C2 C7 C8 -116.92(15) . . . . ? C5 C4 C10 C11 -114.93(15) . . . . ? C3 C4 C10 C11 64.98(18) . . . . ? C5 C4 C10 C12 120.88(15) . . . . ? C3 C4 C10 C12 -59.22(18) . . . . ? C5 C6 C13 C14 -75.89(19) . . . . ? C1 C6 C13 C14 101.95(18) . . . . ? C5 C6 C13 C15 48.70(18) . . . . ? C1 C6 C13 C15 -133.46(15) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.293 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.039 #============================================================================= # end of cif data for "erk6308" #============================================================================= #============================================================================= # end of cif file #============================================================================= _database_code_depnum_ccdc_archive 'CCDC 956700'