# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 222 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'J. McIndoe' 'Danielle M. Chisholm' 'Allen G. Oliver' _publ_contact_author_name 'J. McIndoe' _publ_contact_author_email MCINDOE@UVIC.CA _publ_section_title ; Mono-alkylated bisphosphines as dopants for ESI-MS analysis of catalytic reactions ; # Attachment 'agojsm3.cif' data_agojsm3 _database_code_depnum_ccdc_archive 'CCDC 739029' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C35 H35 P2, F6 P' _chemical_formula_sum 'C35 H35 F6 P3' _chemical_formula_weight 662.54 _chemical_absolute_configuration ad 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' 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 orthorhombic _symmetry_space_group_name_H-M P212121 _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.1738(4) _cell_length_b 15.8803(7) _cell_length_c 19.7059(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3183.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5768 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 25.30 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 0.247 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8915 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Sheldrick, 2008' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II' _diffrn_measurement_method 'combination of \w and \f-scans ' _diffrn_detector_area_resol_mean 83.33 _diffrn_reflns_number 24326 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0501 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 26.46 _reflns_number_total 6483 _reflns_number_gt 5506 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX-II v2009-5' _computing_cell_refinement 'Bruker SAINT v7.60A' _computing_data_reduction 'Bruker SAINT v7.60A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP v5.1' _computing_publication_material 'XCIF (Sheldrick, 2008)' _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 Flack parameter was found to be non-zero. As such the structure was refined as a racemic twin. The Batch Scale Factor (BASF) refined to 0.196(82) indicating an approximately 20% twin (see absolute structure parameter). ; _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^)+(0.0464P)^2^+1.0235P] 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 0.20(8) _refine_ls_number_reflns 6483 _refine_ls_number_parameters 398 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1004 _refine_ls_wR_factor_gt 0.0937 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.43911(6) -0.07444(4) 0.39599(4) 0.02005(16) Uani 1 1 d . . . P2 P 0.66646(7) 0.20173(5) 0.63754(4) 0.02635(17) Uani 1 1 d . . . C1 C 0.4454(3) 0.02584(17) 0.43879(13) 0.0221(6) Uani 1 1 d . . . H1A H 0.4399 0.0714 0.4046 0.027 Uiso 1 1 calc R . . H1B H 0.3682 0.0309 0.4691 0.027 Uiso 1 1 calc R . . C2 C 0.5707(3) 0.03763(19) 0.48077(14) 0.0256(6) Uani 1 1 d . . . H2A H 0.5909 -0.0154 0.5051 0.031 Uiso 1 1 calc R . . H2B H 0.6451 0.0501 0.4500 0.031 Uiso 1 1 calc R . . C3 C 0.5564(3) 0.10887(18) 0.53208(14) 0.0250(6) Uani 1 1 d . . . H3A H 0.4963 0.0909 0.5689 0.030 Uiso 1 1 calc R . . H3B H 0.5168 0.1584 0.5095 0.030 Uiso 1 1 calc R . . C4 C 0.6895(3) 0.13399(19) 0.56284(14) 0.0278(6) Uani 1 1 d . . . H4A H 0.7422 0.1643 0.5284 0.033 Uiso 1 1 calc R . . H4B H 0.7383 0.0827 0.5762 0.033 Uiso 1 1 calc R . . C11 C 0.3929(3) -0.15446(18) 0.45708(14) 0.0248(6) Uani 1 1 d . . . H11A H 0.3792 -0.2083 0.4327 0.030 Uiso 1 1 calc R . . H11B H 0.4666 -0.1627 0.4892 0.030 Uiso 1 1 calc R . . C12 C 0.2707(3) -0.13429(17) 0.49698(13) 0.0225(6) Uani 1 1 d . . . C13 C 0.2820(3) -0.09898(19) 0.56205(14) 0.0275(7) Uani 1 1 d . . . H13A H 0.3666 -0.0859 0.5795 0.033 Uiso 1 1 calc R . . C14 C 0.1726(3) -0.0832(2) 0.60072(15) 0.0323(7) Uani 1 1 d . . . H14A H 0.1820 -0.0591 0.6446 0.039 Uiso 1 1 calc R . . C15 C 0.0482(3) -0.1022(2) 0.57601(16) 0.0341(7) Uani 1 1 d . . . H15A H -0.0275 -0.0921 0.6031 0.041 Uiso 1 1 calc R . . C16 C 0.0354(3) -0.13650(18) 0.51111(16) 0.0299(7) Uani 1 1 d . . . H16A H -0.0494 -0.1490 0.4936 0.036 Uiso 1 1 calc R . . C17 C 0.1460(3) -0.15234(18) 0.47206(14) 0.0269(6) Uani 1 1 d . . . H17A H 0.1366 -0.1757 0.4279 0.032 Uiso 1 1 calc R . . C21 C 0.5979(2) -0.10213(17) 0.36331(14) 0.0220(6) Uani 1 1 d . . . C22 C 0.6514(3) -0.05444(17) 0.31082(14) 0.0251(6) Uani 1 1 d . . . H22A H 0.6018 -0.0100 0.2912 0.030 Uiso 1 1 calc R . . C23 C 0.7763(3) -0.07162(19) 0.28731(15) 0.0292(7) Uani 1 1 d . . . H23A H 0.8129 -0.0389 0.2517 0.035 Uiso 1 1 calc R . . C24 C 0.8481(3) -0.13674(18) 0.31585(14) 0.0276(6) Uani 1 1 d . . . H24A H 0.9340 -0.1487 0.2995 0.033 Uiso 1 1 calc R . . C25 C 0.7961(3) -0.18406(19) 0.36758(15) 0.0294(7) Uani 1 1 d . . . H25A H 0.8461 -0.2284 0.3871 0.035 Uiso 1 1 calc R . . C26 C 0.6703(3) -0.16720(18) 0.39145(15) 0.0273(6) Uani 1 1 d . . . H26A H 0.6340 -0.2003 0.4270 0.033 Uiso 1 1 calc R . . C31 C 0.3230(3) -0.06791(17) 0.32780(13) 0.0216(6) Uani 1 1 d . . . C32 C 0.2263(3) -0.00573(19) 0.32792(15) 0.0277(7) Uani 1 1 d . . . H32A H 0.2221 0.0339 0.3640 0.033 Uiso 1 1 calc R . . C33 C 0.1358(3) -0.00202(19) 0.27488(15) 0.0292(7) Uani 1 1 d . . . H33A H 0.0703 0.0406 0.2745 0.035 Uiso 1 1 calc R . . C34 C 0.1414(3) -0.05962(19) 0.22335(14) 0.0287(7) Uani 1 1 d . . . H34A H 0.0792 -0.0572 0.1875 0.034 Uiso 1 1 calc R . . C35 C 0.2363(3) -0.1208(2) 0.22326(16) 0.0353(7) Uani 1 1 d . . . H35A H 0.2391 -0.1609 0.1875 0.042 Uiso 1 1 calc R . . C36 C 0.3289(3) -0.12475(18) 0.27529(14) 0.0296(6) Uani 1 1 d . . . H36A H 0.3957 -0.1665 0.2745 0.035 Uiso 1 1 calc R . . C41 C 0.5902(3) 0.29445(18) 0.59840(15) 0.0263(6) Uani 1 1 d . . . C42 C 0.4751(3) 0.3245(2) 0.62749(16) 0.0334(7) Uani 1 1 d . . . H42A H 0.4390 0.2964 0.6657 0.040 Uiso 1 1 calc R . . C43 C 0.4120(3) 0.3950(2) 0.60161(17) 0.0384(8) Uani 1 1 d . . . H43A H 0.3336 0.4148 0.6224 0.046 Uiso 1 1 calc R . . C44 C 0.4617(3) 0.4359(2) 0.54664(19) 0.0408(8) Uani 1 1 d . . . H44A H 0.4183 0.4842 0.5291 0.049 Uiso 1 1 calc R . . C45 C 0.5777(3) 0.4062(2) 0.51604(16) 0.0358(7) Uani 1 1 d . . . H45A H 0.6129 0.4343 0.4775 0.043 Uiso 1 1 calc R . . C46 C 0.6406(3) 0.33610(19) 0.54203(14) 0.0284(7) Uani 1 1 d . . . H46A H 0.7189 0.3162 0.5212 0.034 Uiso 1 1 calc R . . C51 C 0.8318(3) 0.24425(17) 0.65345(14) 0.0244(6) Uani 1 1 d . . . C52 C 0.9404(3) 0.23186(18) 0.61195(15) 0.0284(6) Uani 1 1 d . . . H52A H 0.9318 0.1993 0.5718 0.034 Uiso 1 1 calc R . . C53 C 1.0627(3) 0.26680(18) 0.62861(15) 0.0287(7) Uani 1 1 d . . . H53A H 1.1360 0.2583 0.5996 0.034 Uiso 1 1 calc R . . C54 C 1.0765(3) 0.31335(18) 0.68701(15) 0.0293(7) Uani 1 1 d . . . H54A H 1.1597 0.3365 0.6986 0.035 Uiso 1 1 calc R . . C55 C 0.9689(3) 0.32657(19) 0.72902(14) 0.0281(7) Uani 1 1 d . . . H55A H 0.9780 0.3595 0.7690 0.034 Uiso 1 1 calc R . . C56 C 0.8482(3) 0.29167(18) 0.71258(14) 0.0292(7) Uani 1 1 d . . . H56A H 0.7754 0.3001 0.7420 0.035 Uiso 1 1 calc R . . P3 P 0.82858(7) 0.12914(5) 0.14822(4) 0.02550(17) Uani 1 1 d . . . F1 F 0.92418(17) 0.04997(11) 0.14040(9) 0.0409(5) Uani 1 1 d . . . F2 F 0.73054(18) 0.20635(12) 0.15520(10) 0.0473(5) Uani 1 1 d . . . F3 F 0.8681(2) 0.13496(15) 0.22559(10) 0.0656(7) Uani 1 1 d . . . F4 F 0.7859(2) 0.12172(15) 0.07099(9) 0.0600(6) Uani 1 1 d . . . F5 F 0.71247(18) 0.06754(13) 0.16917(11) 0.0562(6) Uani 1 1 d . . . F6 F 0.94375(19) 0.18987(13) 0.12776(15) 0.0778(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 0.0185(3) 0.0203(4) 0.0213(3) 0.0000(3) -0.0007(3) 0.0002(3) P2 0.0271(4) 0.0289(4) 0.0230(4) -0.0012(3) -0.0013(3) -0.0043(3) C1 0.0225(13) 0.0210(15) 0.0227(14) 0.0010(12) -0.0001(11) -0.0023(11) C2 0.0259(14) 0.0235(15) 0.0275(15) -0.0021(12) -0.0040(12) -0.0023(12) C3 0.0275(14) 0.0226(16) 0.0248(14) -0.0028(12) -0.0021(12) -0.0017(12) C4 0.0324(16) 0.0226(16) 0.0286(15) -0.0021(13) -0.0052(12) 0.0004(12) C11 0.0266(15) 0.0217(16) 0.0260(15) 0.0022(13) -0.0007(12) 0.0006(11) C12 0.0222(13) 0.0220(16) 0.0234(15) 0.0058(13) 0.0001(11) -0.0017(11) C13 0.0189(13) 0.0343(18) 0.0292(16) 0.0025(13) -0.0037(11) -0.0045(12) C14 0.0320(15) 0.0414(19) 0.0235(15) 0.0009(14) 0.0050(13) -0.0022(14) C15 0.0250(15) 0.042(2) 0.0358(17) 0.0067(15) 0.0078(13) 0.0004(13) C16 0.0211(14) 0.0273(17) 0.0413(17) 0.0072(15) -0.0032(12) -0.0044(12) C17 0.0268(15) 0.0249(16) 0.0290(15) 0.0008(12) -0.0022(12) -0.0042(12) C21 0.0184(12) 0.0243(15) 0.0234(14) -0.0052(12) -0.0008(11) 0.0003(10) C22 0.0278(14) 0.0196(15) 0.0279(14) 0.0019(12) -0.0024(12) 0.0039(12) C23 0.0292(14) 0.0282(17) 0.0302(16) 0.0031(14) 0.0065(12) -0.0025(13) C24 0.0224(14) 0.0285(17) 0.0319(15) -0.0049(13) 0.0013(12) 0.0008(12) C25 0.0234(14) 0.0298(17) 0.0349(17) 0.0016(14) -0.0040(12) 0.0064(11) C26 0.0252(14) 0.0273(16) 0.0295(15) 0.0054(13) -0.0002(13) 0.0010(12) C31 0.0219(13) 0.0222(15) 0.0206(13) 0.0011(12) -0.0016(11) -0.0026(11) C32 0.0254(14) 0.0267(17) 0.0311(16) -0.0090(13) -0.0028(12) 0.0061(12) C33 0.0221(14) 0.0309(16) 0.0345(17) -0.0017(14) -0.0058(12) 0.0080(12) C34 0.0216(14) 0.0376(19) 0.0268(15) -0.0001(13) -0.0031(11) -0.0008(12) C35 0.0358(17) 0.0336(19) 0.0364(17) -0.0119(15) -0.0086(14) 0.0065(14) C36 0.0276(14) 0.0278(17) 0.0333(16) -0.0041(14) -0.0061(13) 0.0090(13) C41 0.0288(15) 0.0211(15) 0.0290(16) -0.0048(13) -0.0056(12) -0.0053(12) C42 0.0289(15) 0.039(2) 0.0324(17) -0.0053(14) 0.0003(12) -0.0054(13) C43 0.0261(15) 0.040(2) 0.049(2) -0.0116(17) 0.0017(15) 0.0028(13) C44 0.0306(17) 0.0260(18) 0.066(2) -0.0025(17) -0.0163(16) 0.0013(13) C45 0.0376(17) 0.0295(18) 0.0404(18) 0.0034(15) -0.0087(14) -0.0090(14) C46 0.0276(15) 0.0285(17) 0.0292(15) -0.0063(13) -0.0021(12) -0.0024(13) C51 0.0251(14) 0.0213(15) 0.0269(15) 0.0019(12) -0.0065(12) -0.0047(12) C52 0.0279(14) 0.0313(17) 0.0259(15) 0.0000(13) -0.0038(13) 0.0025(12) C53 0.0257(14) 0.0289(17) 0.0315(16) 0.0032(13) -0.0002(12) 0.0021(12) C54 0.0296(15) 0.0273(17) 0.0309(16) 0.0051(14) -0.0082(13) -0.0030(13) C55 0.0358(17) 0.0287(17) 0.0199(14) -0.0028(13) -0.0051(12) -0.0009(13) C56 0.0328(16) 0.0290(17) 0.0256(15) 0.0011(13) 0.0005(12) -0.0021(13) P3 0.0211(3) 0.0281(4) 0.0273(4) 0.0017(3) 0.0012(3) 0.0047(3) F1 0.0370(9) 0.0386(11) 0.0470(11) 0.0071(9) 0.0047(9) 0.0155(8) F2 0.0410(10) 0.0407(12) 0.0604(13) 0.0013(10) 0.0081(10) 0.0214(9) F3 0.0737(15) 0.0814(17) 0.0416(12) -0.0196(12) -0.0205(11) 0.0295(13) F4 0.0697(14) 0.0835(17) 0.0267(10) -0.0036(11) -0.0049(9) 0.0382(12) F5 0.0286(10) 0.0552(13) 0.0847(16) 0.0323(12) -0.0052(10) -0.0042(9) F6 0.0300(11) 0.0471(13) 0.156(3) 0.0421(15) 0.0092(13) -0.0025(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 C31 1.792(3) . ? P1 C21 1.794(3) . ? P1 C1 1.803(3) . ? P1 C11 1.813(3) . ? P2 C41 1.834(3) . ? P2 C4 1.838(3) . ? P2 C51 1.840(3) . ? C1 C2 1.531(4) . ? C2 C3 1.524(4) . ? C3 C4 1.536(4) . ? C11 C12 1.506(4) . ? C12 C17 1.390(4) . ? C12 C13 1.404(4) . ? C13 C14 1.372(4) . ? C14 C15 1.389(4) . ? C15 C16 1.396(4) . ? C16 C17 1.387(4) . ? C21 C26 1.384(4) . ? C21 C22 1.393(4) . ? C22 C23 1.380(4) . ? C23 C24 1.386(4) . ? C24 C25 1.373(4) . ? C25 C26 1.390(4) . ? C31 C36 1.374(4) . ? C31 C32 1.394(4) . ? C32 C33 1.394(4) . ? C33 C34 1.368(4) . ? C34 C35 1.370(4) . ? C35 C36 1.393(4) . ? C41 C42 1.389(4) . ? C41 C46 1.391(4) . ? C42 C43 1.387(4) . ? C43 C44 1.361(5) . ? C44 C45 1.408(5) . ? C45 C46 1.382(4) . ? C51 C52 1.389(4) . ? C51 C56 1.397(4) . ? C52 C53 1.401(4) . ? C53 C54 1.375(4) . ? C54 C55 1.389(4) . ? C55 C56 1.386(4) . ? P3 F6 1.570(2) . ? P3 F3 1.579(2) . ? P3 F2 1.5866(18) . ? P3 F4 1.5871(19) . ? P3 F5 1.5883(19) . ? P3 F1 1.5969(18) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? C22 H22A 0.9500 . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? C25 H25A 0.9500 . ? C26 H26A 0.9500 . ? C32 H32A 0.9500 . ? C33 H33A 0.9500 . ? C34 H34A 0.9500 . ? C35 H35A 0.9500 . ? C36 H36A 0.9500 . ? C42 H42A 0.9500 . ? C43 H43A 0.9500 . ? C44 H44A 0.9500 . ? C45 H45A 0.9500 . ? C46 H46A 0.9500 . ? C52 H52A 0.9500 . ? C53 H53A 0.9500 . ? C54 H54A 0.9500 . ? C55 H55A 0.9500 . ? C56 H56A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C31 P1 C21 109.80(12) . . ? C31 P1 C1 108.86(13) . . ? C21 P1 C1 110.62(12) . . ? C31 P1 C11 111.57(13) . . ? C21 P1 C11 107.47(13) . . ? C1 P1 C11 108.53(13) . . ? C41 P2 C4 100.77(13) . . ? C41 P2 C51 99.43(13) . . ? C4 P2 C51 103.58(13) . . ? C2 C1 P1 112.99(19) . . ? C3 C2 C1 111.7(2) . . ? C2 C3 C4 111.7(2) . . ? C3 C4 P2 110.84(19) . . ? C12 C11 P1 114.3(2) . . ? C17 C12 C13 118.7(2) . . ? C17 C12 C11 121.7(2) . . ? C13 C12 C11 119.6(2) . . ? C14 C13 C12 120.9(3) . . ? C13 C14 C15 120.3(3) . . ? C14 C15 C16 119.4(3) . . ? C17 C16 C15 120.2(3) . . ? C16 C17 C12 120.5(3) . . ? C26 C21 C22 119.7(2) . . ? C26 C21 P1 121.2(2) . . ? C22 C21 P1 119.0(2) . . ? C23 C22 C21 120.1(3) . . ? C22 C23 C24 119.8(3) . . ? C25 C24 C23 120.4(3) . . ? C24 C25 C26 120.1(3) . . ? C21 C26 C25 119.9(3) . . ? C36 C31 C32 119.8(2) . . ? C36 C31 P1 119.9(2) . . ? C32 C31 P1 120.3(2) . . ? C33 C32 C31 119.6(3) . . ? C34 C33 C32 120.1(3) . . ? C33 C34 C35 120.3(3) . . ? C34 C35 C36 120.5(3) . . ? C31 C36 C35 119.7(3) . . ? C42 C41 C46 118.5(3) . . ? C42 C41 P2 117.3(2) . . ? C46 C41 P2 124.2(2) . . ? C43 C42 C41 121.1(3) . . ? C44 C43 C42 120.4(3) . . ? C43 C44 C45 119.5(3) . . ? C46 C45 C44 120.0(3) . . ? C45 C46 C41 120.5(3) . . ? C52 C51 C56 118.2(3) . . ? C52 C51 P2 125.1(2) . . ? C56 C51 P2 116.7(2) . . ? C51 C52 C53 120.8(3) . . ? C54 C53 C52 120.0(3) . . ? C53 C54 C55 120.0(3) . . ? C56 C55 C54 119.9(3) . . ? C55 C56 C51 121.1(3) . . ? F6 P3 F3 91.25(15) . . ? F6 P3 F2 90.96(11) . . ? F3 P3 F2 91.79(11) . . ? F6 P3 F4 90.20(14) . . ? F3 P3 F4 178.55(15) . . ? F2 P3 F4 88.20(11) . . ? F6 P3 F5 179.75(14) . . ? F3 P3 F5 88.54(13) . . ? F2 P3 F5 89.19(11) . . ? F4 P3 F5 90.01(13) . . ? F6 P3 F1 90.24(11) . . ? F3 P3 F1 89.09(11) . . ? F2 P3 F1 178.49(11) . . ? F4 P3 F1 90.89(11) . . ? F5 P3 F1 89.61(10) . . ? C2 C1 H1A 109.0 . . ? P1 C1 H1A 109.0 . . ? C2 C1 H1B 109.0 . . ? P1 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 107.9 . . ? C3 C4 H4A 109.5 . . ? P2 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? P2 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C12 C11 H11A 108.7 . . ? P1 C11 H11A 108.7 . . ? C12 C11 H11B 108.7 . . ? P1 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C14 C13 H13A 119.6 . . ? C12 C13 H13A 119.6 . . ? C13 C14 H14A 119.8 . . ? C15 C14 H14A 119.8 . . ? C14 C15 H15A 120.3 . . ? C16 C15 H15A 120.3 . . ? C17 C16 H16A 119.9 . . ? C15 C16 H16A 119.9 . . ? C16 C17 H17A 119.8 . . ? C12 C17 H17A 119.8 . . ? C23 C22 H22A 119.9 . . ? C21 C22 H22A 119.9 . . ? C22 C23 H23A 120.1 . . ? C24 C23 H23A 120.1 . . ? C25 C24 H24A 119.8 . . ? C23 C24 H24A 119.8 . . ? C24 C25 H25A 120.0 . . ? C26 C25 H25A 120.0 . . ? C21 C26 H26A 120.1 . . ? C25 C26 H26A 120.1 . . ? C33 C32 H32A 120.2 . . ? C31 C32 H32A 120.2 . . ? C34 C33 H33A 120.0 . . ? C32 C33 H33A 120.0 . . ? C33 C34 H34A 119.8 . . ? C35 C34 H34A 119.8 . . ? C34 C35 H35A 119.8 . . ? C36 C35 H35A 119.8 . . ? C31 C36 H36A 120.1 . . ? C35 C36 H36A 120.1 . . ? C43 C42 H42A 119.5 . . ? C41 C42 H42A 119.5 . . ? C44 C43 H43A 119.8 . . ? C42 C43 H43A 119.8 . . ? C43 C44 H44A 120.3 . . ? C45 C44 H44A 120.3 . . ? C46 C45 H45A 120.0 . . ? C44 C45 H45A 120.0 . . ? C45 C46 H46A 119.7 . . ? C41 C46 H46A 119.7 . . ? C51 C52 H52A 119.6 . . ? C53 C52 H52A 119.6 . . ? C54 C53 H53A 120.0 . . ? C52 C53 H53A 120.0 . . ? C53 C54 H54A 120.0 . . ? C55 C54 H54A 120.0 . . ? C56 C55 H55A 120.0 . . ? C54 C55 H55A 120.0 . . ? C55 C56 H56A 119.5 . . ? C51 C56 H56A 119.5 . . ? 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 C31 P1 C1 C2 -160.38(19) . . . . ? C21 P1 C1 C2 -39.7(2) . . . . ? C11 P1 C1 C2 78.0(2) . . . . ? P1 C1 C2 C3 -163.0(2) . . . . ? C1 C2 C3 C4 -167.2(2) . . . . ? C2 C3 C4 P2 -167.0(2) . . . . ? C41 P2 C4 C3 -64.4(2) . . . . ? C51 P2 C4 C3 -167.0(2) . . . . ? C31 P1 C11 C12 -68.1(2) . . . . ? C21 P1 C11 C12 171.52(19) . . . . ? C1 P1 C11 C12 51.9(2) . . . . ? P1 C11 C12 C17 84.8(3) . . . . ? P1 C11 C12 C13 -97.4(3) . . . . ? C17 C12 C13 C14 0.6(4) . . . . ? C11 C12 C13 C14 -177.3(3) . . . . ? C12 C13 C14 C15 0.2(5) . . . . ? C13 C14 C15 C16 -0.9(5) . . . . ? C14 C15 C16 C17 0.8(5) . . . . ? C15 C16 C17 C12 -0.1(4) . . . . ? C13 C12 C17 C16 -0.6(4) . . . . ? C11 C12 C17 C16 177.2(3) . . . . ? C31 P1 C21 C26 -130.1(2) . . . . ? C1 P1 C21 C26 109.7(2) . . . . ? C11 P1 C21 C26 -8.6(3) . . . . ? C31 P1 C21 C22 53.0(3) . . . . ? C1 P1 C21 C22 -67.2(2) . . . . ? C11 P1 C21 C22 174.5(2) . . . . ? C26 C21 C22 C23 -0.5(4) . . . . ? P1 C21 C22 C23 176.5(2) . . . . ? C21 C22 C23 C24 0.3(4) . . . . ? C22 C23 C24 C25 -0.3(4) . . . . ? C23 C24 C25 C26 0.4(4) . . . . ? C22 C21 C26 C25 0.6(4) . . . . ? P1 C21 C26 C25 -176.3(2) . . . . ? C24 C25 C26 C21 -0.5(4) . . . . ? C21 P1 C31 C36 38.5(3) . . . . ? C1 P1 C31 C36 159.7(2) . . . . ? C11 P1 C31 C36 -80.6(2) . . . . ? C21 P1 C31 C32 -141.9(2) . . . . ? C1 P1 C31 C32 -20.7(3) . . . . ? C11 P1 C31 C32 99.1(2) . . . . ? C36 C31 C32 C33 0.3(4) . . . . ? P1 C31 C32 C33 -179.3(2) . . . . ? C31 C32 C33 C34 0.6(4) . . . . ? C32 C33 C34 C35 -0.5(4) . . . . ? C33 C34 C35 C36 -0.5(5) . . . . ? C32 C31 C36 C35 -1.3(4) . . . . ? P1 C31 C36 C35 178.3(2) . . . . ? C34 C35 C36 C31 1.4(5) . . . . ? C4 P2 C41 C42 129.4(2) . . . . ? C51 P2 C41 C42 -124.7(2) . . . . ? C4 P2 C41 C46 -50.8(3) . . . . ? C51 P2 C41 C46 55.1(3) . . . . ? C46 C41 C42 C43 -0.6(4) . . . . ? P2 C41 C42 C43 179.2(2) . . . . ? C41 C42 C43 C44 0.3(5) . . . . ? C42 C43 C44 C45 0.1(5) . . . . ? C43 C44 C45 C46 -0.3(5) . . . . ? C44 C45 C46 C41 0.0(4) . . . . ? C42 C41 C46 C45 0.5(4) . . . . ? P2 C41 C46 C45 -179.3(2) . . . . ? C41 P2 C51 C52 -97.7(3) . . . . ? C4 P2 C51 C52 5.9(3) . . . . ? C41 P2 C51 C56 83.2(2) . . . . ? C4 P2 C51 C56 -173.3(2) . . . . ? C56 C51 C52 C53 -0.7(4) . . . . ? P2 C51 C52 C53 -179.8(2) . . . . ? C51 C52 C53 C54 0.6(4) . . . . ? C52 C53 C54 C55 -0.8(4) . . . . ? C53 C54 C55 C56 1.0(4) . . . . ? C54 C55 C56 C51 -1.1(4) . . . . ? C52 C51 C56 C55 1.0(4) . . . . ? P2 C51 C56 C55 -179.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.46 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.407 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.053