# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Prof. Bernhard Breit' _publ_contact_author_address ; Albert-Ludwigs-Universitat Institut fur Organische Chemie und Biochemie Albertstr. 21 D-79104 Freiburg Germany ; _publ_contact_author_email bernhard.breit@orgmail.chemie.uni-freiburg.de _publ_contact_author_phone 0049-0761-203-6051 _publ_contact_author_fax 0049-0761-203-8715 loop_ _publ_author_name _publ_author_address 'Bernhard Breit' ; Institut fur Organische Chemie und Biochemie Albertstr. 21 D-79104 Freiburg Germany ; 'Evelyn Fuchs' ; Institut fur Organische Chemie und Biochemie Albertstr. 21 D-79104 Freiburg Germany ; _publ_section_title ; Phosphabarrelene-rhodium complexes as highly active catalysts for isomerization free hydroformylation of internal alkenes ; #========================================================================== data_ef1 _database_code_depnum_ccdc_archive 'CCDC 222357' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Triphenyl-phosphabarrelen (4a) ; _chemical_name_common 'Triphenyl-phosphabarrelen (4a)' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H21 P' _chemical_formula_weight 400.43 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 7.3015(1) _cell_length_b 18.5002(3) _cell_length_c 31.4241(5) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 4244.74(11) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 9294 _cell_measurement_theta_min 2 _cell_measurement_theta_max 28 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.25 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.945 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 NONIUS_KappaCCD _diffrn_measurement_method '\p-and \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8686 _diffrn_reflns_av_R_equivalents 0.032 _diffrn_reflns_av_sigmaI/netI 0.049 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 27.87 _reflns_number_total 4851 _reflns_number_gt 3171 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.2810P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4851 _refine_ls_number_parameters 355 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.082 _refine_ls_R_factor_gt 0.044 _refine_ls_wR_factor_ref 0.116 _refine_ls_wR_factor_gt 0.103 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.04185(6) 0.23255(2) 0.123970(15) 0.04340(16) Uani 1 1 d . . . C1 C -0.2086(2) 0.23421(8) 0.13186(5) 0.0403(4) Uani 1 1 d . . . C2 C -0.2977(2) 0.17552(8) 0.11880(5) 0.0390(4) Uani 1 1 d . . . C3 C -0.19409(19) 0.11222(8) 0.09893(5) 0.0359(4) Uani 1 1 d . . . C4 C -0.0458(2) 0.09033(9) 0.13094(5) 0.0386(4) Uani 1 1 d . . . C5 C 0.0749(2) 0.13919(8) 0.14456(5) 0.0388(4) Uani 1 1 d . . . C6 C 0.0302(2) 0.20091(9) 0.06871(5) 0.0423(4) Uani 1 1 d . . . C7 C -0.08514(19) 0.14173(8) 0.06022(5) 0.0390(4) Uani 1 1 d . . . C8 C -0.0868(2) 0.11176(11) 0.02022(6) 0.0477(4) Uani 1 1 d . . . C9 C 0.0232(3) 0.14055(13) -0.01171(7) 0.0616(5) Uani 1 1 d . . . C10 C 0.1331(3) 0.19923(13) -0.00393(7) 0.0664(6) Uani 1 1 d . . . C11 C 0.1375(2) 0.22943(11) 0.03625(7) 0.0553(5) Uani 1 1 d . . . C12 C -0.3009(2) 0.29564(8) 0.15324(5) 0.0412(4) Uani 1 1 d . . . C13 C -0.4734(2) 0.31838(9) 0.14035(7) 0.0479(4) Uani 1 1 d . . . C14 C -0.5653(3) 0.37311(10) 0.16138(7) 0.0589(5) Uani 1 1 d . . . C15 C -0.4854(3) 0.40725(11) 0.19544(7) 0.0624(5) Uani 1 1 d . . . C16 C -0.3144(3) 0.38599(11) 0.20854(7) 0.0679(6) Uani 1 1 d . . . C17 C -0.2214(3) 0.33113(11) 0.18756(6) 0.0572(5) Uani 1 1 d . . . C18 C -0.32732(19) 0.05244(8) 0.08614(5) 0.0373(4) Uani 1 1 d . . . C19 C -0.2999(3) -0.01991(9) 0.09462(6) 0.0512(5) Uani 1 1 d . . . C20 C -0.4272(3) -0.07104(11) 0.08262(7) 0.0651(6) Uani 1 1 d . . . C21 C -0.5836(3) -0.05131(11) 0.06198(7) 0.0624(6) Uani 1 1 d . . . C22 C -0.6134(3) 0.02000(11) 0.05240(7) 0.0592(5) Uani 1 1 d . . . C23 C -0.4857(2) 0.07106(10) 0.06405(6) 0.0501(5) Uani 1 1 d . . . C24 C 0.23664(19) 0.12285(8) 0.17126(5) 0.0377(4) Uani 1 1 d . . . C25 C 0.3145(2) 0.17472(10) 0.19776(5) 0.0448(4) Uani 1 1 d . . . C26 C 0.4652(2) 0.15859(12) 0.22254(6) 0.0571(5) Uani 1 1 d . . . C27 C 0.5423(3) 0.09090(12) 0.22108(7) 0.0611(5) Uani 1 1 d . . . C28 C 0.4694(3) 0.03964(12) 0.19473(7) 0.0582(5) Uani 1 1 d . . . C29 C 0.3181(2) 0.05525(10) 0.16985(6) 0.0471(4) Uani 1 1 d . . . H2 H -0.427(2) 0.1716(9) 0.1237(5) 0.050(5) Uiso 1 1 d . . . H4 H -0.0426(19) 0.0413(9) 0.1408(5) 0.033(4) Uiso 1 1 d . . . H8 H -0.155(2) 0.0711(9) 0.0148(5) 0.039(4) Uiso 1 1 d . . . H9 H 0.023(3) 0.1168(10) -0.0381(7) 0.067(6) Uiso 1 1 d . . . H10 H 0.206(3) 0.2176(10) -0.0270(7) 0.072(6) Uiso 1 1 d . . . H11 H 0.219(3) 0.2716(10) 0.0430(6) 0.069(6) Uiso 1 1 d . . . H13 H -0.531(2) 0.2954(11) 0.1179(6) 0.055(5) Uiso 1 1 d . . . H14 H -0.686(3) 0.3863(10) 0.1529(7) 0.072(6) Uiso 1 1 d . . . H15 H -0.543(3) 0.4469(12) 0.2106(6) 0.072(6) Uiso 1 1 d . . . H16 H -0.254(3) 0.4064(12) 0.2327(8) 0.100(8) Uiso 1 1 d . . . H17 H -0.108(3) 0.3140(11) 0.1964(6) 0.068(6) Uiso 1 1 d . . . H19 H -0.193(2) -0.0346(9) 0.1087(6) 0.053(5) Uiso 1 1 d . . . H20 H -0.402(3) -0.1201(12) 0.0885(7) 0.084(7) Uiso 1 1 d . . . H21 H -0.669(3) -0.0857(11) 0.0534(6) 0.070(6) Uiso 1 1 d . . . H22 H -0.725(3) 0.0373(10) 0.0383(7) 0.078(6) Uiso 1 1 d . . . H23 H -0.509(2) 0.1177(10) 0.0581(6) 0.051(5) Uiso 1 1 d . . . H25 H 0.269(2) 0.2213(9) 0.1982(5) 0.046(5) Uiso 1 1 d . . . H26 H 0.518(3) 0.1953(12) 0.2414(7) 0.082(6) Uiso 1 1 d . . . H27 H 0.643(3) 0.0816(10) 0.2383(7) 0.077(6) Uiso 1 1 d . . . H28 H 0.520(3) -0.0068(11) 0.1919(7) 0.069(6) Uiso 1 1 d . . . H29 H 0.275(2) 0.0204(9) 0.1500(6) 0.048(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0305(3) 0.0387(3) 0.0610(3) 0.0073(2) -0.00382(18) -0.00531(17) C1 0.0343(9) 0.0367(9) 0.0500(10) 0.0039(7) -0.0021(7) -0.0022(7) C2 0.0297(9) 0.0395(9) 0.0476(10) 0.0046(7) 0.0000(7) -0.0023(7) C3 0.0309(8) 0.0344(8) 0.0424(9) 0.0046(6) -0.0035(7) -0.0018(6) C4 0.0345(9) 0.0357(9) 0.0455(10) 0.0077(7) -0.0041(7) -0.0023(7) C5 0.0334(8) 0.0408(9) 0.0421(10) 0.0052(7) -0.0020(7) -0.0025(7) C6 0.0313(8) 0.0411(9) 0.0544(10) 0.0126(8) 0.0002(7) 0.0018(7) C7 0.0294(8) 0.0424(9) 0.0452(10) 0.0095(7) -0.0020(7) 0.0055(7) C8 0.0392(9) 0.0564(12) 0.0474(11) 0.0066(9) -0.0037(8) 0.0048(8) C9 0.0516(11) 0.0871(16) 0.0461(12) 0.0090(11) 0.0043(9) 0.0101(11) C10 0.0487(11) 0.0897(16) 0.0608(15) 0.0249(12) 0.0146(10) 0.0014(11) C11 0.0376(10) 0.0609(12) 0.0675(14) 0.0222(10) 0.0066(9) -0.0028(8) C12 0.0377(9) 0.0361(9) 0.0498(10) 0.0024(7) 0.0030(7) -0.0086(7) C13 0.0408(10) 0.0416(10) 0.0612(12) -0.0028(9) 0.0001(9) -0.0032(7) C14 0.0463(11) 0.0465(11) 0.0839(15) -0.0023(10) 0.0105(10) 0.0025(8) C15 0.0672(13) 0.0509(12) 0.0693(14) -0.0095(11) 0.0197(11) -0.0036(10) C16 0.0815(16) 0.0635(14) 0.0588(14) -0.0167(10) 0.0029(11) -0.0130(11) C17 0.0517(11) 0.0570(12) 0.0629(13) -0.0033(10) -0.0075(10) -0.0042(9) C18 0.0347(8) 0.0385(9) 0.0385(9) 0.0019(7) -0.0020(7) -0.0017(6) C19 0.0505(11) 0.0416(10) 0.0614(12) 0.0019(8) -0.0191(9) -0.0003(8) C20 0.0780(14) 0.0385(11) 0.0789(15) 0.0076(10) -0.0302(11) -0.0115(10) C21 0.0623(12) 0.0562(13) 0.0687(14) 0.0006(10) -0.0212(10) -0.0214(10) C22 0.0445(11) 0.0617(13) 0.0714(14) -0.0037(10) -0.0210(10) -0.0032(9) C23 0.0471(10) 0.0392(10) 0.0641(12) 0.0036(9) -0.0146(9) 0.0010(8) C24 0.0308(8) 0.0440(9) 0.0382(9) 0.0060(7) -0.0006(6) -0.0047(7) C25 0.0397(9) 0.0489(11) 0.0458(10) 0.0024(8) -0.0008(8) -0.0057(8) C26 0.0491(11) 0.0693(13) 0.0530(12) -0.0007(10) -0.0139(9) -0.0117(9) C27 0.0478(11) 0.0766(15) 0.0589(13) 0.0085(11) -0.0193(10) 0.0004(10) C28 0.0524(11) 0.0591(13) 0.0632(13) 0.0043(10) -0.0116(9) 0.0114(9) C29 0.0413(10) 0.0507(11) 0.0492(11) 0.0000(9) -0.0066(8) 0.0004(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C6 1.8345(18) . ? P1 C1 1.8454(16) . ? P1 C5 1.8601(16) . ? C1 C2 1.331(2) . ? C1 C12 1.482(2) . ? C2 C3 1.527(2) . ? C2 H2 0.961(18) . ? C3 C18 1.527(2) . ? C3 C4 1.533(2) . ? C3 C7 1.553(2) . ? C4 C5 1.333(2) . ? C4 H4 0.959(16) . ? C5 C24 1.480(2) . ? C6 C11 1.390(2) . ? C6 C7 1.407(2) . ? C7 C8 1.374(2) . ? C8 C9 1.392(3) . ? C8 H8 0.916(15) . ? C9 C10 1.372(3) . ? C9 H9 0.94(2) . ? C10 C11 1.381(3) . ? C10 H10 0.96(2) . ? C11 H11 1.01(2) . ? C12 C13 1.388(2) . ? C12 C17 1.390(2) . ? C13 C14 1.383(3) . ? C13 H13 0.925(19) . ? C14 C15 1.373(3) . ? C14 H14 0.95(2) . ? C15 C16 1.372(3) . ? C15 H15 0.97(2) . ? C16 C17 1.388(3) . ? C16 H16 0.96(3) . ? C17 H17 0.93(2) . ? C18 C19 1.379(2) . ? C18 C23 1.392(2) . ? C19 C20 1.379(2) . ? C19 H19 0.936(18) . ? C20 C21 1.363(3) . ? C20 H20 0.94(2) . ? C21 C22 1.371(3) . ? C21 H21 0.93(2) . ? C22 C23 1.377(3) . ? C22 H22 0.98(2) . ? C23 H23 0.898(17) . ? C24 C29 1.386(2) . ? C24 C25 1.392(2) . ? C25 C26 1.381(2) . ? C25 H25 0.924(16) . ? C26 C27 1.374(3) . ? C26 H26 0.98(2) . ? C27 C28 1.367(3) . ? C27 H27 0.93(2) . ? C28 C29 1.384(3) . ? C28 H28 0.94(2) . ? C29 H29 0.952(17) . ? 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 C6 P1 C1 94.95(7) . . ? C6 P1 C5 92.23(7) . . ? C1 P1 C5 95.57(7) . . ? C2 C1 C12 122.88(15) . . ? C2 C1 P1 115.43(12) . . ? C12 C1 P1 121.62(11) . . ? C1 C2 C3 120.64(14) . . ? C1 C2 H2 119.5(10) . . ? C3 C2 H2 119.7(10) . . ? C18 C3 C2 110.34(12) . . ? C18 C3 C4 115.58(12) . . ? C2 C3 C4 106.51(13) . . ? C18 C3 C7 112.01(13) . . ? C2 C3 C7 107.72(12) . . ? C4 C3 C7 104.19(11) . . ? C5 C4 C3 119.90(14) . . ? C5 C4 H4 121.5(9) . . ? C3 C4 H4 118.6(9) . . ? C4 C5 C24 124.81(14) . . ? C4 C5 P1 115.63(12) . . ? C24 C5 P1 119.36(11) . . ? C11 C6 C7 119.57(17) . . ? C11 C6 P1 123.17(14) . . ? C7 C6 P1 117.12(12) . . ? C8 C7 C6 119.54(15) . . ? C8 C7 C3 124.77(15) . . ? C6 C7 C3 115.57(14) . . ? C7 C8 C9 120.01(19) . . ? C7 C8 H8 120.3(10) . . ? C9 C8 H8 119.5(10) . . ? C10 C9 C8 120.8(2) . . ? C10 C9 H9 121.8(12) . . ? C8 C9 H9 117.3(12) . . ? C9 C10 C11 119.77(19) . . ? C9 C10 H10 118.0(12) . . ? C11 C10 H10 122.2(12) . . ? C10 C11 C6 120.29(19) . . ? C10 C11 H11 121.4(12) . . ? C6 C11 H11 118.3(12) . . ? C13 C12 C17 117.52(17) . . ? C13 C12 C1 120.86(15) . . ? C17 C12 C1 121.59(15) . . ? C14 C13 C12 121.52(19) . . ? C14 C13 H13 118.8(12) . . ? C12 C13 H13 119.7(12) . . ? C15 C14 C13 120.2(2) . . ? C15 C14 H14 119.5(12) . . ? C13 C14 H14 120.2(12) . . ? C16 C15 C14 119.3(2) . . ? C16 C15 H15 117.6(12) . . ? C14 C15 H15 123.2(12) . . ? C15 C16 C17 120.8(2) . . ? C15 C16 H16 123.0(14) . . ? C17 C16 H16 116.1(15) . . ? C16 C17 C12 120.6(2) . . ? C16 C17 H17 123.0(13) . . ? C12 C17 H17 116.2(13) . . ? C19 C18 C23 117.19(15) . . ? C19 C18 C3 124.03(13) . . ? C23 C18 C3 118.77(14) . . ? C20 C19 C18 121.01(17) . . ? C20 C19 H19 119.4(10) . . ? C18 C19 H19 119.6(10) . . ? C21 C20 C19 120.74(18) . . ? C21 C20 H20 121.1(13) . . ? C19 C20 H20 118.1(13) . . ? C20 C21 C22 119.67(18) . . ? C20 C21 H21 121.2(12) . . ? C22 C21 H21 119.1(12) . . ? C21 C22 C23 119.65(18) . . ? C21 C22 H22 123.0(12) . . ? C23 C22 H22 117.3(12) . . ? C22 C23 C18 121.70(17) . . ? C22 C23 H23 118.4(11) . . ? C18 C23 H23 119.8(11) . . ? C29 C24 C25 117.77(15) . . ? C29 C24 C5 120.59(14) . . ? C25 C24 C5 121.62(14) . . ? C26 C25 C24 120.93(18) . . ? C26 C25 H25 118.6(11) . . ? C24 C25 H25 120.4(11) . . ? C27 C26 C25 120.30(19) . . ? C27 C26 H26 119.5(13) . . ? C25 C26 H26 120.2(13) . . ? C28 C27 C26 119.56(18) . . ? C28 C27 H27 122.2(12) . . ? C26 C27 H27 118.3(12) . . ? C27 C28 C29 120.56(19) . . ? C27 C28 H28 122.7(12) . . ? C29 C28 H28 116.8(12) . . ? C28 C29 C24 120.87(18) . . ? C28 C29 H29 119.6(10) . . ? C24 C29 H29 119.3(10) . . ? 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 47.13(14) . . . . ? C5 P1 C1 C2 -45.60(14) . . . . ? C6 P1 C1 C12 -135.70(13) . . . . ? C5 P1 C1 C12 131.57(13) . . . . ? C12 C1 C2 C3 -176.95(14) . . . . ? P1 C1 C2 C3 0.2(2) . . . . ? C1 C2 C3 C18 -179.16(14) . . . . ? C1 C2 C3 C4 54.67(19) . . . . ? C1 C2 C3 C7 -56.62(18) . . . . ? C18 C3 C4 C5 -178.86(14) . . . . ? C2 C3 C4 C5 -55.92(19) . . . . ? C7 C3 C4 C5 57.81(19) . . . . ? C3 C4 C5 C24 -172.36(14) . . . . ? C3 C4 C5 P1 2.4(2) . . . . ? C6 P1 C5 C4 -50.92(14) . . . . ? C1 P1 C5 C4 44.28(14) . . . . ? C6 P1 C5 C24 124.19(13) . . . . ? C1 P1 C5 C24 -140.61(13) . . . . ? C1 P1 C6 C11 136.35(14) . . . . ? C5 P1 C6 C11 -127.86(14) . . . . ? C1 P1 C6 C7 -47.95(13) . . . . ? C5 P1 C6 C7 47.84(12) . . . . ? C11 C6 C7 C8 1.6(2) . . . . ? P1 C6 C7 C8 -174.27(12) . . . . ? C11 C6 C7 C3 177.94(13) . . . . ? P1 C6 C7 C3 2.08(17) . . . . ? C18 C3 C7 C8 -8.7(2) . . . . ? C2 C3 C7 C8 -130.23(16) . . . . ? C4 C3 C7 C8 116.91(16) . . . . ? C18 C3 C7 C6 175.16(12) . . . . ? C2 C3 C7 C6 53.64(16) . . . . ? C4 C3 C7 C6 -59.21(16) . . . . ? C6 C7 C8 C9 -0.8(2) . . . . ? C3 C7 C8 C9 -176.82(14) . . . . ? C7 C8 C9 C10 -0.6(3) . . . . ? C8 C9 C10 C11 1.2(3) . . . . ? C9 C10 C11 C6 -0.4(3) . . . . ? C7 C6 C11 C10 -1.0(2) . . . . ? P1 C6 C11 C10 174.64(14) . . . . ? C2 C1 C12 C13 -38.4(2) . . . . ? P1 C1 C12 C13 144.60(14) . . . . ? C2 C1 C12 C17 139.59(18) . . . . ? P1 C1 C12 C17 -37.4(2) . . . . ? C17 C12 C13 C14 -1.5(3) . . . . ? C1 C12 C13 C14 176.61(16) . . . . ? C12 C13 C14 C15 1.0(3) . . . . ? C13 C14 C15 C16 -0.6(3) . . . . ? C14 C15 C16 C17 0.6(3) . . . . ? C15 C16 C17 C12 -1.2(3) . . . . ? C13 C12 C17 C16 1.6(3) . . . . ? C1 C12 C17 C16 -176.55(17) . . . . ? C2 C3 C18 C19 -134.25(16) . . . . ? C4 C3 C18 C19 -13.4(2) . . . . ? C7 C3 C18 C19 105.76(18) . . . . ? C2 C3 C18 C23 46.6(2) . . . . ? C4 C3 C18 C23 167.51(15) . . . . ? C7 C3 C18 C23 -73.37(18) . . . . ? C23 C18 C19 C20 -1.7(3) . . . . ? C3 C18 C19 C20 179.15(18) . . . . ? C18 C19 C20 C21 0.1(3) . . . . ? C19 C20 C21 C22 1.1(3) . . . . ? C20 C21 C22 C23 -0.6(3) . . . . ? C21 C22 C23 C18 -1.2(3) . . . . ? C19 C18 C23 C22 2.3(3) . . . . ? C3 C18 C23 C22 -178.55(18) . . . . ? C4 C5 C24 C29 27.1(2) . . . . ? P1 C5 C24 C29 -147.54(13) . . . . ? C4 C5 C24 C25 -154.37(17) . . . . ? P1 C5 C24 C25 31.0(2) . . . . ? C29 C24 C25 C26 -1.5(2) . . . . ? C5 C24 C25 C26 179.87(16) . . . . ? C24 C25 C26 C27 0.7(3) . . . . ? C25 C26 C27 C28 0.4(3) . . . . ? C26 C27 C28 C29 -0.5(3) . . . . ? C27 C28 C29 C24 -0.4(3) . . . . ? C25 C24 C29 C28 1.4(3) . . . . ? C5 C24 C29 C28 -179.99(16) . . . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.208 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.037