# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'G Erker' 'Klaus Bergander' 'Roland Frohlich' 'Gerald Kehr' 'Patrick Spies' 'Birgit Wibbeling' _publ_contact_author_name 'G Erker' _publ_contact_author_email ERKER@UNI-MUENSTER.DE _publ_section_title ; Metal-free dihydrogen activation chemistry: structural and dynamic features of intramolecular P/B pairs ; # Attachment 'ERK4229.CIF' data_erk4229 _database_code_depnum_ccdc_archive 'CCDC 701817' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H28 B F10 P' _chemical_formula_weight 656.33 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 12.0881(5) _cell_length_b 10.3454(5) _cell_length_c 24.1019(12) _cell_angle_alpha 90.00 _cell_angle_beta 101.884(3) _cell_angle_gamma 90.00 _cell_volume 2949.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4743 _cell_measurement_theta_min 0.88 _cell_measurement_theta_max 68.25 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 1.612 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7387 _exptl_absorpt_correction_T_max 0.9237 _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 20597 _diffrn_reflns_av_R_equivalents 0.062 _diffrn_reflns_av_sigmaI/netI 0.0924 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 4.67 _diffrn_reflns_theta_max 68.12 _reflns_number_total 5064 _reflns_number_gt 2801 _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 'SCHAKAL (Keller, 1997)' _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^)+(0.0707P)^2^+9.8016P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5064 _refine_ls_number_parameters 412 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1658 _refine_ls_R_factor_gt 0.0842 _refine_ls_wR_factor_ref 0.2277 _refine_ls_wR_factor_gt 0.1752 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.28325(13) 0.83397(16) 0.13670(7) 0.0412(4) Uani 1 1 d . . . C1 C 0.2970(5) 0.9446(6) 0.1968(3) 0.0448(15) Uani 1 1 d . . . H1A H 0.3220 1.0298 0.1866 0.054 Uiso 1 1 calc R . . H1B H 0.2240 0.9545 0.2081 0.054 Uiso 1 1 calc R . . C2 C 0.3861(6) 0.8855(6) 0.2467(3) 0.0472(16) Uani 1 1 d . . . H2A H 0.4554 0.9374 0.2529 0.057 Uiso 1 1 calc R . . H2B H 0.3564 0.8872 0.2816 0.057 Uiso 1 1 calc R . . C3 C 0.4132(5) 0.7452(6) 0.2327(3) 0.0461(16) Uani 1 1 d . . . H3A H 0.3495 0.6888 0.2356 0.055 Uiso 1 1 calc R . . H3B H 0.4801 0.7148 0.2597 0.055 Uiso 1 1 calc R . . B1 B 0.4363(6) 0.7401(7) 0.1691(3) 0.0426(17) Uani 1 1 d . . . C11 C 0.1717(5) 0.7109(6) 0.1346(2) 0.0420(15) Uani 1 1 d . . . C12 C 0.1104(5) 0.6868(6) 0.1778(2) 0.0412(15) Uani 1 1 d . . . C121 C 0.1152(5) 0.7687(7) 0.2308(3) 0.0515(17) Uani 1 1 d . . . H12A H 0.0704 0.7280 0.2550 0.077 Uiso 1 1 calc R . . H12B H 0.0853 0.8541 0.2200 0.077 Uiso 1 1 calc R . . H12C H 0.1930 0.7761 0.2511 0.077 Uiso 1 1 calc R . . C13 C 0.0370(5) 0.5824(7) 0.1722(3) 0.0489(17) Uani 1 1 d . . . H13 H -0.0034 0.5675 0.2010 0.059 Uiso 1 1 calc R . . C14 C 0.0206(6) 0.4998(7) 0.1266(3) 0.0511(17) Uani 1 1 d . . . C141 C -0.0576(8) 0.3844(8) 0.1249(3) 0.084(3) Uani 1 1 d . . . H14A H -0.1356 0.4133 0.1153 0.127 Uiso 1 1 calc R . . H14B H -0.0435 0.3427 0.1617 0.127 Uiso 1 1 calc R . . H14C H -0.0437 0.3235 0.0965 0.127 Uiso 1 1 calc R . . C15 C 0.0780(5) 0.5236(6) 0.0849(3) 0.0474(16) Uani 1 1 d . . . H15 H 0.0677 0.4676 0.0535 0.057 Uiso 1 1 calc R . . C16 C 0.1517(5) 0.6281(7) 0.0866(2) 0.0462(16) Uani 1 1 d . . . C161 C 0.2084(6) 0.6435(7) 0.0371(3) 0.0510(17) Uani 1 1 d . . . H16A H 0.2890 0.6552 0.0508 0.077 Uiso 1 1 calc R . . H16B H 0.1775 0.7184 0.0150 0.077 Uiso 1 1 calc R . . H16C H 0.1952 0.5669 0.0135 0.077 Uiso 1 1 calc R . . C21 C 0.2386(5) 0.9411(6) 0.0744(3) 0.0428(15) Uani 1 1 d . . . C22 C 0.1424(5) 1.0205(6) 0.0719(3) 0.0444(15) Uani 1 1 d . . . C221 C 0.0639(6) 1.0157(7) 0.1136(3) 0.0580(19) Uani 1 1 d . . . H22A H -0.0111 1.0434 0.0948 0.087 Uiso 1 1 calc R . . H22B H 0.0923 1.0726 0.1453 0.087 Uiso 1 1 calc R . . H22C H 0.0603 0.9279 0.1273 0.087 Uiso 1 1 calc R . . C23 C 0.1164(6) 1.1118(6) 0.0286(3) 0.0500(17) Uani 1 1 d . . . H23 H 0.0523 1.1644 0.0268 0.060 Uiso 1 1 calc R . . C24 C 0.1811(6) 1.1279(7) -0.0119(3) 0.0527(17) Uani 1 1 d . . . C241 C 0.1553(6) 1.2334(8) -0.0563(3) 0.069(2) Uani 1 1 d . . . H24A H 0.1931 1.3125 -0.0414 0.104 Uiso 1 1 calc R . . H24B H 0.0743 1.2479 -0.0661 0.104 Uiso 1 1 calc R . . H24C H 0.1819 1.2072 -0.0900 0.104 Uiso 1 1 calc R . . C25 C 0.2706(5) 1.0456(6) -0.0106(3) 0.0471(16) Uani 1 1 d . . . H25 H 0.3130 1.0520 -0.0391 0.057 Uiso 1 1 calc R . . C26 C 0.3008(5) 0.9524(6) 0.0320(3) 0.0455(16) Uani 1 1 d . . . C261 C 0.4020(5) 0.8692(7) 0.0280(3) 0.0521(18) Uani 1 1 d . . . H26A H 0.4246 0.8197 0.0627 0.078 Uiso 1 1 calc R . . H26B H 0.4641 0.9240 0.0227 0.078 Uiso 1 1 calc R . . H26C H 0.3821 0.8106 -0.0039 0.078 Uiso 1 1 calc R . . C31 C 0.4425(5) 0.5975(6) 0.1401(2) 0.0415(15) Uani 1 1 d . . . C32 C 0.5091(5) 0.5701(6) 0.1007(2) 0.0409(15) Uani 1 1 d . . . F32 F 0.5773(3) 0.6604(3) 0.08519(15) 0.0522(9) Uani 1 1 d . . . C33 C 0.5149(6) 0.4509(6) 0.0760(3) 0.0460(16) Uani 1 1 d . . . F33 F 0.5837(3) 0.4315(4) 0.03946(16) 0.0638(11) Uani 1 1 d . . . C34 C 0.4476(6) 0.3532(6) 0.0876(3) 0.0496(17) Uani 1 1 d . . . F34 F 0.4481(4) 0.2378(4) 0.06133(18) 0.0714(12) Uani 1 1 d . . . C35 C 0.3816(6) 0.3719(6) 0.1265(3) 0.0497(17) Uani 1 1 d . . . F35 F 0.3166(3) 0.2755(4) 0.14007(17) 0.0665(11) Uani 1 1 d . . . C36 C 0.3810(5) 0.4926(6) 0.1520(2) 0.0373(14) Uani 1 1 d . . . F36 F 0.3166(3) 0.4977(3) 0.19153(14) 0.0502(9) Uani 1 1 d . . . C41 C 0.5513(5) 0.8273(6) 0.1704(2) 0.0423(15) Uani 1 1 d . . . C42 C 0.6544(5) 0.7718(7) 0.1956(3) 0.0480(16) Uani 1 1 d . . . F42 F 0.6570(3) 0.6482(4) 0.21409(17) 0.0620(11) Uani 1 1 d . . . C43 C 0.7574(5) 0.8332(7) 0.2024(3) 0.0549(18) Uani 1 1 d . . . F43 F 0.8527(3) 0.7707(4) 0.2271(2) 0.0790(13) Uani 1 1 d . . . C44 C 0.7627(6) 0.9577(7) 0.1831(3) 0.0502(17) Uani 1 1 d . . . F44 F 0.8636(3) 1.0156(4) 0.18784(19) 0.0746(13) Uani 1 1 d . . . C45 C 0.6647(6) 1.0180(6) 0.1597(3) 0.0472(16) Uani 1 1 d . . . F45 F 0.6680(3) 1.1419(4) 0.14191(17) 0.0663(11) Uani 1 1 d . . . C46 C 0.5629(5) 0.9542(6) 0.1547(3) 0.0449(16) Uani 1 1 d . . . F46 F 0.4698(3) 1.0253(4) 0.13179(16) 0.0579(10) 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 0.0413(9) 0.0398(10) 0.0406(8) -0.0022(7) 0.0040(7) 0.0029(7) C1 0.053(4) 0.032(4) 0.048(4) 0.002(3) 0.007(3) 0.009(3) C2 0.056(4) 0.043(4) 0.040(3) -0.007(3) 0.004(3) -0.008(3) C3 0.043(4) 0.042(4) 0.050(4) 0.002(3) 0.001(3) -0.002(3) B1 0.039(4) 0.041(5) 0.046(4) 0.007(3) 0.003(3) -0.001(3) C11 0.038(3) 0.044(4) 0.040(3) -0.001(3) 0.001(3) 0.011(3) C12 0.038(3) 0.044(4) 0.038(3) 0.001(3) 0.000(3) 0.002(3) C121 0.049(4) 0.061(5) 0.046(4) -0.007(3) 0.014(3) -0.001(3) C13 0.046(4) 0.054(5) 0.047(4) 0.006(3) 0.009(3) -0.005(3) C14 0.062(4) 0.044(4) 0.043(4) 0.002(3) 0.001(3) -0.009(3) C141 0.110(7) 0.071(6) 0.070(5) -0.001(5) 0.012(5) -0.043(5) C15 0.061(4) 0.039(4) 0.037(3) -0.003(3) -0.003(3) -0.008(3) C16 0.048(4) 0.052(4) 0.037(3) 0.000(3) 0.003(3) 0.005(3) C161 0.057(4) 0.050(5) 0.042(4) -0.004(3) 0.001(3) 0.003(3) C21 0.047(4) 0.037(4) 0.043(3) -0.003(3) 0.006(3) 0.004(3) C22 0.043(4) 0.037(4) 0.052(4) -0.002(3) 0.007(3) 0.003(3) C221 0.056(4) 0.054(5) 0.065(4) 0.007(4) 0.015(4) 0.022(4) C23 0.051(4) 0.041(4) 0.056(4) 0.006(3) 0.006(3) 0.012(3) C24 0.052(4) 0.049(5) 0.051(4) 0.011(3) -0.003(3) 0.007(3) C241 0.070(5) 0.065(5) 0.068(5) 0.023(4) 0.004(4) 0.010(4) C25 0.050(4) 0.047(4) 0.042(4) 0.010(3) 0.004(3) 0.010(3) C26 0.039(4) 0.049(4) 0.046(4) -0.006(3) 0.002(3) 0.000(3) C261 0.052(4) 0.051(5) 0.055(4) 0.009(3) 0.015(3) 0.011(3) C31 0.042(4) 0.035(4) 0.044(3) 0.004(3) 0.001(3) -0.002(3) C32 0.049(4) 0.037(4) 0.037(3) 0.006(3) 0.011(3) 0.005(3) F32 0.056(2) 0.045(2) 0.059(2) 0.0050(18) 0.0210(18) 0.0014(19) C33 0.060(4) 0.041(4) 0.038(3) 0.008(3) 0.011(3) 0.009(3) F33 0.079(3) 0.059(3) 0.059(2) -0.003(2) 0.027(2) 0.014(2) C34 0.069(5) 0.032(4) 0.044(4) -0.005(3) 0.004(3) 0.011(3) F34 0.096(3) 0.040(3) 0.077(3) -0.007(2) 0.017(2) 0.004(2) C35 0.056(4) 0.036(4) 0.053(4) 0.008(3) 0.003(3) 0.002(3) F35 0.078(3) 0.042(2) 0.080(3) -0.002(2) 0.016(2) -0.014(2) C36 0.039(3) 0.036(4) 0.036(3) 0.002(3) 0.006(3) 0.004(3) F36 0.054(2) 0.043(2) 0.053(2) 0.0038(17) 0.0112(18) -0.0003(17) C41 0.047(4) 0.038(4) 0.040(3) 0.000(3) 0.005(3) 0.005(3) C42 0.042(4) 0.044(4) 0.054(4) 0.004(3) 0.002(3) 0.003(3) F42 0.051(2) 0.049(3) 0.080(3) 0.014(2) 0.001(2) 0.0048(19) C43 0.034(4) 0.065(5) 0.063(4) -0.003(4) 0.004(3) 0.016(4) F43 0.045(2) 0.078(3) 0.107(3) 0.000(3) -0.003(2) 0.008(2) C44 0.047(4) 0.048(5) 0.056(4) -0.005(3) 0.010(3) -0.010(3) F44 0.049(2) 0.082(3) 0.095(3) -0.011(3) 0.019(2) -0.024(2) C45 0.051(4) 0.038(4) 0.053(4) 0.000(3) 0.012(3) -0.005(3) F45 0.073(3) 0.050(3) 0.074(3) 0.002(2) 0.009(2) -0.017(2) C46 0.042(4) 0.043(4) 0.049(4) 0.004(3) 0.007(3) 0.004(3) F46 0.052(2) 0.040(2) 0.076(3) 0.0096(19) -0.0009(19) 0.0029(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 C1 1.827(6) . ? P1 C11 1.848(7) . ? P1 C21 1.856(6) . ? P1 B1 2.092(7) . ? C1 C2 1.563(8) . ? C2 C3 1.541(9) . ? C3 B1 1.615(9) . ? B1 C31 1.641(10) . ? B1 C41 1.651(9) . ? C11 C16 1.418(8) . ? C11 C12 1.420(8) . ? C12 C13 1.386(9) . ? C12 C121 1.523(8) . ? C13 C14 1.374(9) . ? C14 C15 1.358(9) . ? C14 C141 1.517(9) . ? C15 C16 1.396(9) . ? C16 C161 1.503(8) . ? C21 C26 1.392(8) . ? C21 C22 1.415(8) . ? C22 C23 1.396(9) . ? C22 C221 1.517(8) . ? C23 C24 1.381(9) . ? C24 C25 1.372(9) . ? C24 C241 1.515(9) . ? C25 C26 1.400(8) . ? C26 C261 1.515(8) . ? C31 C36 1.379(8) . ? C31 C32 1.394(8) . ? C32 F32 1.349(7) . ? C32 C33 1.377(9) . ? C33 F33 1.346(7) . ? C33 C34 1.363(9) . ? C34 F34 1.352(7) . ? C34 C35 1.364(9) . ? C35 F35 1.351(7) . ? C35 C36 1.392(9) . ? C36 F36 1.350(6) . ? C41 C46 1.382(9) . ? C41 C42 1.393(8) . ? C42 F42 1.353(7) . ? C42 C43 1.377(9) . ? C43 F43 1.348(7) . ? C43 C44 1.376(10) . ? C44 F44 1.344(7) . ? C44 C45 1.355(9) . ? C45 F45 1.355(7) . ? C45 C46 1.379(9) . ? C46 F46 1.362(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 P1 C11 113.6(3) . . ? C1 P1 C21 103.4(3) . . ? C11 P1 C21 107.5(3) . . ? C1 P1 B1 93.8(3) . . ? C11 P1 B1 106.0(3) . . ? C21 P1 B1 131.8(3) . . ? C2 C1 P1 107.5(4) . . ? C3 C2 C1 110.1(5) . . ? C2 C3 B1 108.9(5) . . ? C3 B1 C31 117.7(5) . . ? C3 B1 C41 105.8(5) . . ? C31 B1 C41 112.8(5) . . ? C3 B1 P1 91.5(4) . . ? C31 B1 P1 111.9(4) . . ? C41 B1 P1 115.5(4) . . ? C16 C11 C12 117.7(6) . . ? C16 C11 P1 116.1(4) . . ? C12 C11 P1 126.1(5) . . ? C13 C12 C11 119.1(6) . . ? C13 C12 C121 115.4(5) . . ? C11 C12 C121 125.6(6) . . ? C14 C13 C12 123.1(6) . . ? C15 C14 C13 117.9(6) . . ? C15 C14 C141 122.2(6) . . ? C13 C14 C141 119.9(6) . . ? C14 C15 C16 122.6(6) . . ? C15 C16 C11 119.5(6) . . ? C15 C16 C161 116.8(6) . . ? C11 C16 C161 123.7(6) . . ? C26 C21 C22 119.0(6) . . ? C26 C21 P1 122.2(5) . . ? C22 C21 P1 118.6(4) . . ? C23 C22 C21 118.7(6) . . ? C23 C22 C221 116.2(6) . . ? C21 C22 C221 125.1(6) . . ? C24 C23 C22 122.5(6) . . ? C25 C24 C23 117.9(6) . . ? C25 C24 C241 120.7(6) . . ? C23 C24 C241 121.4(6) . . ? C24 C25 C26 122.0(6) . . ? C21 C26 C25 119.7(6) . . ? C21 C26 C261 124.3(6) . . ? C25 C26 C261 115.9(5) . . ? C36 C31 C32 113.2(6) . . ? C36 C31 B1 123.0(5) . . ? C32 C31 B1 123.8(5) . . ? F32 C32 C33 114.3(5) . . ? F32 C32 C31 121.3(5) . . ? C33 C32 C31 124.3(6) . . ? F33 C33 C34 120.0(6) . . ? F33 C33 C32 120.6(6) . . ? C34 C33 C32 119.4(6) . . ? F34 C34 C33 119.9(6) . . ? F34 C34 C35 120.5(6) . . ? C33 C34 C35 119.6(6) . . ? F35 C35 C34 120.8(6) . . ? F35 C35 C36 120.0(6) . . ? C34 C35 C36 119.2(6) . . ? F36 C36 C31 122.0(5) . . ? F36 C36 C35 113.8(5) . . ? C31 C36 C35 124.2(5) . . ? C46 C41 C42 112.3(6) . . ? C46 C41 B1 130.2(6) . . ? C42 C41 B1 117.2(6) . . ? F42 C42 C43 115.9(6) . . ? F42 C42 C41 119.4(6) . . ? C43 C42 C41 124.7(6) . . ? F43 C43 C44 120.3(6) . . ? F43 C43 C42 120.1(7) . . ? C44 C43 C42 119.6(6) . . ? F44 C44 C45 122.1(6) . . ? F44 C44 C43 119.6(6) . . ? C45 C44 C43 118.4(6) . . ? C44 C45 F45 119.1(6) . . ? C44 C45 C46 120.3(6) . . ? F45 C45 C46 120.6(6) . . ? F46 C46 C45 115.1(6) . . ? F46 C46 C41 120.2(6) . . ? C45 C46 C41 124.7(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 P1 C1 C2 91.0(5) . . . . ? C21 P1 C1 C2 -152.8(4) . . . . ? B1 P1 C1 C2 -18.2(5) . . . . ? P1 C1 C2 C3 -11.3(6) . . . . ? C1 C2 C3 B1 47.3(7) . . . . ? C2 C3 B1 C31 -168.3(5) . . . . ? C2 C3 B1 C41 64.5(6) . . . . ? C2 C3 B1 P1 -52.5(5) . . . . ? C1 P1 B1 C3 39.5(4) . . . . ? C11 P1 B1 C3 -76.4(4) . . . . ? C21 P1 B1 C3 151.2(4) . . . . ? C1 P1 B1 C31 160.3(4) . . . . ? C11 P1 B1 C31 44.5(5) . . . . ? C21 P1 B1 C31 -88.0(5) . . . . ? C1 P1 B1 C41 -68.9(5) . . . . ? C11 P1 B1 C41 175.3(4) . . . . ? C21 P1 B1 C41 42.9(6) . . . . ? C1 P1 C11 C16 175.7(5) . . . . ? C21 P1 C11 C16 61.9(5) . . . . ? B1 P1 C11 C16 -82.8(5) . . . . ? C1 P1 C11 C12 -8.7(6) . . . . ? C21 P1 C11 C12 -122.5(5) . . . . ? B1 P1 C11 C12 92.8(6) . . . . ? C16 C11 C12 C13 1.8(9) . . . . ? P1 C11 C12 C13 -173.7(5) . . . . ? C16 C11 C12 C121 -176.5(6) . . . . ? P1 C11 C12 C121 7.9(9) . . . . ? C11 C12 C13 C14 0.3(10) . . . . ? C121 C12 C13 C14 178.8(6) . . . . ? C12 C13 C14 C15 -1.1(10) . . . . ? C12 C13 C14 C141 177.4(7) . . . . ? C13 C14 C15 C16 -0.3(10) . . . . ? C141 C14 C15 C16 -178.7(7) . . . . ? C14 C15 C16 C11 2.4(10) . . . . ? C14 C15 C16 C161 -179.2(6) . . . . ? C12 C11 C16 C15 -3.1(9) . . . . ? P1 C11 C16 C15 172.9(5) . . . . ? C12 C11 C16 C161 178.6(6) . . . . ? P1 C11 C16 C161 -5.4(8) . . . . ? C1 P1 C21 C26 121.6(5) . . . . ? C11 P1 C21 C26 -118.0(5) . . . . ? B1 P1 C21 C26 13.9(7) . . . . ? C1 P1 C21 C22 -54.0(6) . . . . ? C11 P1 C21 C22 66.4(5) . . . . ? B1 P1 C21 C22 -161.7(5) . . . . ? C26 C21 C22 C23 -3.1(9) . . . . ? P1 C21 C22 C23 172.7(5) . . . . ? C26 C21 C22 C221 177.5(6) . . . . ? P1 C21 C22 C221 -6.7(9) . . . . ? C21 C22 C23 C24 -0.2(10) . . . . ? C221 C22 C23 C24 179.2(6) . . . . ? C22 C23 C24 C25 3.5(10) . . . . ? C22 C23 C24 C241 -176.1(7) . . . . ? C23 C24 C25 C26 -3.6(10) . . . . ? C241 C24 C25 C26 176.0(7) . . . . ? C22 C21 C26 C25 3.0(9) . . . . ? P1 C21 C26 C25 -172.6(5) . . . . ? C22 C21 C26 C261 -177.0(6) . . . . ? P1 C21 C26 C261 7.4(9) . . . . ? C24 C25 C26 C21 0.4(10) . . . . ? C24 C25 C26 C261 -179.6(6) . . . . ? C3 B1 C31 C36 31.6(9) . . . . ? C41 B1 C31 C36 155.3(6) . . . . ? P1 B1 C31 C36 -72.5(7) . . . . ? C3 B1 C31 C32 -149.1(6) . . . . ? C41 B1 C31 C32 -25.3(8) . . . . ? P1 B1 C31 C32 106.8(6) . . . . ? C36 C31 C32 F32 -178.1(5) . . . . ? B1 C31 C32 F32 2.5(9) . . . . ? C36 C31 C32 C33 -0.5(9) . . . . ? B1 C31 C32 C33 -179.9(6) . . . . ? F32 C32 C33 F33 -0.4(8) . . . . ? C31 C32 C33 F33 -178.2(6) . . . . ? F32 C32 C33 C34 -178.5(6) . . . . ? C31 C32 C33 C34 3.7(10) . . . . ? F33 C33 C34 F34 -1.6(10) . . . . ? C32 C33 C34 F34 176.5(6) . . . . ? F33 C33 C34 C35 177.2(6) . . . . ? C32 C33 C34 C35 -4.7(10) . . . . ? F34 C34 C35 F35 0.8(10) . . . . ? C33 C34 C35 F35 -178.0(6) . . . . ? F34 C34 C35 C36 -178.6(6) . . . . ? C33 C34 C35 C36 2.6(10) . . . . ? C32 C31 C36 F36 176.0(5) . . . . ? B1 C31 C36 F36 -4.6(9) . . . . ? C32 C31 C36 C35 -1.8(9) . . . . ? B1 C31 C36 C35 177.7(6) . . . . ? F35 C35 C36 F36 3.5(8) . . . . ? C34 C35 C36 F36 -177.2(5) . . . . ? F35 C35 C36 C31 -178.6(6) . . . . ? C34 C35 C36 C31 0.7(10) . . . . ? C3 B1 C41 C46 -97.9(7) . . . . ? C31 B1 C41 C46 132.0(7) . . . . ? P1 B1 C41 C46 1.6(9) . . . . ? C3 B1 C41 C42 75.8(7) . . . . ? C31 B1 C41 C42 -54.3(7) . . . . ? P1 B1 C41 C42 175.3(5) . . . . ? C46 C41 C42 F42 179.1(5) . . . . ? B1 C41 C42 F42 4.2(8) . . . . ? C46 C41 C42 C43 -2.2(9) . . . . ? B1 C41 C42 C43 -177.0(6) . . . . ? F42 C42 C43 F43 -0.9(9) . . . . ? C41 C42 C43 F43 -179.7(6) . . . . ? F42 C42 C43 C44 178.0(6) . . . . ? C41 C42 C43 C44 -0.8(10) . . . . ? F43 C43 C44 F44 1.5(10) . . . . ? C42 C43 C44 F44 -177.4(6) . . . . ? F43 C43 C44 C45 -178.6(6) . . . . ? C42 C43 C44 C45 2.5(10) . . . . ? F44 C44 C45 F45 -1.9(9) . . . . ? C43 C44 C45 F45 178.1(6) . . . . ? F44 C44 C45 C46 178.8(6) . . . . ? C43 C44 C45 C46 -1.1(10) . . . . ? C44 C45 C46 F46 178.5(6) . . . . ? F45 C45 C46 F46 -0.8(9) . . . . ? C44 C45 C46 C41 -2.2(10) . . . . ? F45 C45 C46 C41 178.5(6) . . . . ? C42 C41 C46 F46 -177.0(5) . . . . ? B1 C41 C46 F46 -3.1(10) . . . . ? C42 C41 C46 C45 3.7(9) . . . . ? B1 C41 C46 C45 177.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 68.12 _diffrn_measured_fraction_theta_full 0.939 _refine_diff_density_max 0.359 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.083