# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Sascha Ott' _publ_contact_author_email SASCHA.OTT@FOTOMOL.UU.SE _publ_section_title ; Exploitation of an unprecedented silica-promoted acetylene-allene rearrangement for the preparation of C,C-diacetylenic phosphaalkenes ; loop_ _publ_author_name 'Sascha Ott' 'Xue-Li Geng.' # Attachment 'X-ray_compound_4.cif' data_r90605d _database_code_depnum_ccdc_archive 'CCDC 743457' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C58 H68 P2' _chemical_formula_weight 827.06 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.4252(19) _cell_length_b 26.239(5) _cell_length_c 10.502(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.39(3) _cell_angle_gamma 90.00 _cell_volume 2562.5(9) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 3828 _cell_measurement_theta_min 2.113 _cell_measurement_theta_max 25.284 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.072 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 892 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9765 _exptl_absorpt_correction_T_max 0.9858 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 18817 _diffrn_reflns_av_R_equivalents 0.0560 _diffrn_reflns_av_sigmaI/netI 0.0558 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4524 _reflns_number_gt 3262 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'crystalclear(Rigaku/MSC Inc., 2005)' _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0920P)^2^+0.9769P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment CONSTR _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.012(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4524 _refine_ls_number_parameters 300 _refine_ls_number_restraints 72 _refine_ls_R_factor_all 0.1153 _refine_ls_R_factor_gt 0.0841 _refine_ls_wR_factor_ref 0.2211 _refine_ls_wR_factor_gt 0.1989 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.139 _refine_ls_shift/su_max 0.004 _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 0.30771(11) 0.53013(4) 0.75210(10) 0.0608(4) Uani 1 1 d . . . C1 C 0.4014(3) 0.57605(12) 0.6621(3) 0.0473(8) Uani 1 1 d . . . C2 C 0.5222(4) 0.60409(13) 0.7277(3) 0.0530(9) Uani 1 1 d . . . C3 C 0.5898(4) 0.63832(13) 0.6551(3) 0.0576(9) Uani 1 1 d . . . H3A H 0.6675 0.6570 0.6972 0.069 Uiso 1 1 calc R . . C4 C 0.5477(4) 0.64595(13) 0.5247(3) 0.0575(9) Uani 1 1 d . A . C5 C 0.4337(4) 0.61684(13) 0.4635(3) 0.0560(9) Uani 1 1 d . . . H5A H 0.4051 0.6213 0.3751 0.067 Uiso 1 1 calc R . . C6 C 0.3596(4) 0.58134(13) 0.5262(3) 0.0514(8) Uani 1 1 d . . . C7 C 0.2397(4) 0.55015(14) 0.4415(3) 0.0609(9) Uani 1 1 d . . . C8 C 0.2378(5) 0.55946(19) 0.2957(4) 0.0951(16) Uani 1 1 d . . . H8A H 0.2232 0.5951 0.2771 0.143 Uiso 1 1 calc R . . H8B H 0.1611 0.5402 0.2468 0.143 Uiso 1 1 calc R . . H8C H 0.3279 0.5489 0.2729 0.143 Uiso 1 1 calc R . . C9 C 0.2631(5) 0.49267(15) 0.4609(4) 0.0802(12) Uani 1 1 d . . . H9A H 0.2647 0.4843 0.5501 0.120 Uiso 1 1 calc R . . H9B H 0.3531 0.4832 0.4360 0.120 Uiso 1 1 calc R . . H9C H 0.1863 0.4745 0.4087 0.120 Uiso 1 1 calc R . . C10 C 0.0895(4) 0.56578(18) 0.4660(4) 0.0848(13) Uani 1 1 d . . . H10A H 0.0831 0.5606 0.5553 0.127 Uiso 1 1 calc R . . H10B H 0.0182 0.5454 0.4134 0.127 Uiso 1 1 calc R . . H10C H 0.0734 0.6011 0.4445 0.127 Uiso 1 1 calc R . . C11 C 0.6269(5) 0.68247(16) 0.4472(4) 0.0800(13) Uani 1 1 d D . . C12 C 0.7837(11) 0.6617(6) 0.4620(16) 0.114(4) Uani 0.382(7) 1 d PDU A 1 H12A H 0.8353 0.6710 0.5452 0.171 Uiso 0.382(7) 1 calc PR A 1 H12B H 0.8308 0.6760 0.3959 0.171 Uiso 0.382(7) 1 calc PR A 1 H12C H 0.7815 0.6252 0.4540 0.171 Uiso 0.382(7) 1 calc PR A 1 C13 C 0.648(2) 0.7327(4) 0.5322(13) 0.112(5) Uani 0.382(7) 1 d PDU A 1 H13A H 0.5797 0.7333 0.5903 0.169 Uiso 0.382(7) 1 calc PR A 1 H13B H 0.6348 0.7620 0.4769 0.169 Uiso 0.382(7) 1 calc PR A 1 H13C H 0.7440 0.7331 0.5809 0.169 Uiso 0.382(7) 1 calc PR A 1 C14 C 0.5489(19) 0.6953(8) 0.3142(11) 0.134(5) Uani 0.382(7) 1 d PDU A 1 H14A H 0.4808 0.7221 0.3201 0.201 Uiso 0.382(7) 1 calc PR A 1 H14B H 0.4992 0.6657 0.2763 0.201 Uiso 0.382(7) 1 calc PR A 1 H14C H 0.6170 0.7064 0.2613 0.201 Uiso 0.382(7) 1 calc PR A 1 C12' C 0.6772(11) 0.6516(3) 0.3354(9) 0.122(3) Uani 0.618(7) 1 d PDU A 2 H12D H 0.7485 0.6271 0.3710 0.182 Uiso 0.618(7) 1 calc PR A 2 H12E H 0.7176 0.6745 0.2797 0.182 Uiso 0.618(7) 1 calc PR A 2 H12F H 0.5963 0.6342 0.2869 0.182 Uiso 0.618(7) 1 calc PR A 2 C13' C 0.7477(11) 0.7116(4) 0.5217(9) 0.128(4) Uani 0.618(7) 1 d PDU A 2 H13D H 0.7140 0.7300 0.5898 0.192 Uiso 0.618(7) 1 calc PR A 2 H13E H 0.7851 0.7351 0.4654 0.192 Uiso 0.618(7) 1 calc PR A 2 H13F H 0.8223 0.6884 0.5580 0.192 Uiso 0.618(7) 1 calc PR A 2 C14' C 0.5143(10) 0.7200(4) 0.3745(11) 0.124(4) Uani 0.618(7) 1 d PDU A 2 H14D H 0.4762 0.7410 0.4359 0.186 Uiso 0.618(7) 1 calc PR A 2 H14E H 0.4377 0.7011 0.3244 0.186 Uiso 0.618(7) 1 calc PR A 2 H14F H 0.5596 0.7412 0.3184 0.186 Uiso 0.618(7) 1 calc PR A 2 C15 C 0.5886(4) 0.59867(16) 0.8738(3) 0.0660(10) Uani 1 1 d . . . C16 C 0.4894(6) 0.6224(2) 0.9593(4) 0.115(2) Uani 1 1 d . . . H16A H 0.3970 0.6061 0.9425 0.172 Uiso 1 1 calc R . . H16B H 0.4785 0.6581 0.9407 0.172 Uiso 1 1 calc R . . H16C H 0.5304 0.6178 1.0484 0.172 Uiso 1 1 calc R . . C17 C 0.6214(6) 0.54289(18) 0.9106(4) 0.0999(16) Uani 1 1 d . . . H17A H 0.5344 0.5233 0.8934 0.150 Uiso 1 1 calc R . . H17B H 0.6606 0.5408 1.0008 0.150 Uiso 1 1 calc R . . H17C H 0.6899 0.5297 0.8607 0.150 Uiso 1 1 calc R . . C18 C 0.7348(5) 0.6260(2) 0.9057(4) 0.0987(16) Uani 1 1 d . . . H18A H 0.7224 0.6617 0.8861 0.148 Uiso 1 1 calc R . . H18B H 0.8009 0.6116 0.8552 0.148 Uiso 1 1 calc R . . H18C H 0.7722 0.6219 0.9958 0.148 Uiso 1 1 calc R . . C19 C 0.1778(4) 0.56530(13) 0.8066(3) 0.0553(9) Uani 1 1 d . . . C20 C 0.1495(4) 0.61777(15) 0.7772(3) 0.0570(9) Uani 1 1 d . . . C21 C 0.1360(4) 0.66142(15) 0.7459(3) 0.0599(9) Uani 1 1 d . . . C22 C 0.1296(4) 0.71341(14) 0.7011(3) 0.0583(9) Uani 1 1 d . . . C23 C 0.2133(5) 0.72823(16) 0.6114(4) 0.0765(12) Uani 1 1 d . . . H23A H 0.2746 0.7049 0.5819 0.092 Uiso 1 1 calc R . . C24 C 0.2065(6) 0.77756(19) 0.5651(4) 0.0925(15) Uani 1 1 d . . . H24A H 0.2625 0.7870 0.5039 0.111 Uiso 1 1 calc R . . C25 C 0.1188(6) 0.81241(17) 0.6081(5) 0.0923(15) Uani 1 1 d . . . H25A H 0.1148 0.8455 0.5761 0.111 Uiso 1 1 calc R . . C26 C 0.0371(6) 0.79898(17) 0.6976(5) 0.0961(15) Uani 1 1 d . . . H26A H -0.0220 0.8231 0.7275 0.115 Uiso 1 1 calc R . . C27 C 0.0412(5) 0.74915(17) 0.7455(4) 0.0805(12) Uani 1 1 d . . . H27A H -0.0152 0.7401 0.8067 0.097 Uiso 1 1 calc R . . C28 C 0.0957(4) 0.53868(14) 0.8884(3) 0.0596(9) Uani 1 1 d . . . C29 C 0.0341(4) 0.51435(14) 0.9595(3) 0.0592(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 0.0689(7) 0.0530(6) 0.0665(6) 0.0144(5) 0.0289(5) 0.0010(5) C1 0.050(2) 0.0443(18) 0.0514(18) 0.0056(14) 0.0189(15) 0.0045(15) C2 0.057(2) 0.053(2) 0.0517(19) 0.0042(16) 0.0161(17) 0.0070(16) C3 0.054(2) 0.057(2) 0.063(2) 0.0000(17) 0.0109(17) -0.0063(17) C4 0.053(2) 0.060(2) 0.063(2) 0.0108(17) 0.0199(18) -0.0044(17) C5 0.058(2) 0.064(2) 0.0481(18) 0.0083(16) 0.0151(17) -0.0027(17) C6 0.048(2) 0.054(2) 0.056(2) -0.0008(16) 0.0190(16) -0.0027(16) C7 0.057(2) 0.064(2) 0.062(2) -0.0038(18) 0.0123(17) -0.0065(18) C8 0.116(4) 0.110(4) 0.059(2) -0.012(2) 0.013(3) -0.032(3) C9 0.081(3) 0.063(3) 0.097(3) -0.012(2) 0.017(2) -0.010(2) C10 0.057(3) 0.101(3) 0.094(3) -0.010(3) 0.007(2) -0.002(2) C11 0.075(3) 0.081(3) 0.089(3) 0.022(2) 0.029(2) -0.015(2) C12 0.105(7) 0.118(8) 0.131(8) 0.019(6) 0.056(6) -0.019(6) C13 0.112(8) 0.098(8) 0.131(8) 0.031(6) 0.031(7) -0.031(7) C14 0.155(9) 0.141(9) 0.113(8) 0.045(7) 0.043(7) -0.027(7) C12' 0.135(6) 0.134(6) 0.117(6) 0.005(5) 0.084(5) -0.035(5) C13' 0.107(6) 0.135(7) 0.139(6) 0.028(5) 0.013(5) -0.068(5) C14' 0.138(7) 0.106(6) 0.132(7) 0.056(5) 0.033(6) -0.021(5) C15 0.067(3) 0.078(3) 0.053(2) 0.0004(19) 0.0073(18) 0.005(2) C16 0.096(4) 0.183(6) 0.065(3) -0.046(3) 0.010(3) 0.020(4) C17 0.110(4) 0.100(4) 0.083(3) 0.032(3) -0.004(3) 0.006(3) C18 0.080(3) 0.125(4) 0.082(3) 0.002(3) -0.014(3) -0.007(3) C19 0.059(2) 0.061(2) 0.0507(18) 0.0104(16) 0.0213(17) -0.0027(17) C20 0.058(2) 0.063(2) 0.054(2) 0.0074(18) 0.0215(17) 0.0030(18) C21 0.058(2) 0.069(3) 0.056(2) 0.0030(19) 0.0191(17) 0.0004(19) C22 0.063(2) 0.054(2) 0.058(2) 0.0034(17) 0.0113(18) -0.0017(18) C23 0.090(3) 0.069(3) 0.076(3) 0.008(2) 0.030(2) 0.002(2) C24 0.121(4) 0.080(3) 0.081(3) 0.015(3) 0.030(3) -0.009(3) C25 0.124(4) 0.060(3) 0.090(3) 0.013(2) 0.007(3) -0.001(3) C26 0.118(4) 0.062(3) 0.110(4) 0.002(3) 0.024(3) 0.024(3) C27 0.088(3) 0.072(3) 0.087(3) 0.004(2) 0.031(2) 0.011(2) C28 0.058(2) 0.067(2) 0.058(2) 0.0084(18) 0.0210(18) -0.0022(18) C29 0.052(2) 0.074(2) 0.054(2) 0.0115(18) 0.0164(17) -0.0018(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 C19 1.705(4) . ? P1 C1 1.843(3) . ? C1 C6 1.424(5) . ? C1 C2 1.433(5) . ? C2 C3 1.397(5) . ? C2 C15 1.567(5) . ? C3 C4 1.377(5) . ? C3 H3A 0.9300 . ? C4 C5 1.387(5) . ? C4 C11 1.528(5) . ? C5 C6 1.393(4) . ? C5 H5A 0.9300 . ? C6 C7 1.553(5) . ? C7 C9 1.533(5) . ? C7 C10 1.535(5) . ? C7 C8 1.547(5) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C13' 1.483(7) . ? C11 C14 1.507(9) . ? C11 C14' 1.554(7) . ? C11 C12 1.559(9) . ? C11 C12' 1.563(7) . ? C11 C13 1.586(9) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C12' H12D 0.9600 . ? C12' H12E 0.9600 . ? C12' H12F 0.9600 . ? C13' H13D 0.9600 . ? C13' H13E 0.9600 . ? C13' H13F 0.9600 . ? C14' H14D 0.9600 . ? C14' H14E 0.9600 . ? C14' H14F 0.9600 . ? C15 C16 1.531(6) . ? C15 C17 1.532(6) . ? C15 C18 1.541(6) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.427(5) . ? C19 C28 1.429(4) . ? C20 C21 1.193(5) . ? C21 C22 1.441(5) . ? C22 C23 1.379(5) . ? C22 C27 1.385(5) . ? C23 C24 1.380(6) . ? C23 H23A 0.9300 . ? C24 C25 1.358(6) . ? C24 H24A 0.9300 . ? C25 C26 1.355(6) . ? C25 H25A 0.9300 . ? C26 C27 1.399(6) . ? C26 H26A 0.9300 . ? C27 H27A 0.9300 . ? C28 C29 1.201(4) . ? C29 C29 1.373(6) 3_567 ? 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 C19 P1 C1 104.40(15) . . ? C6 C1 C2 120.0(3) . . ? C6 C1 P1 120.0(3) . . ? C2 C1 P1 119.9(2) . . ? C3 C2 C1 117.7(3) . . ? C3 C2 C15 116.6(3) . . ? C1 C2 C15 125.7(3) . . ? C4 C3 C2 123.6(3) . . ? C4 C3 H3A 118.2 . . ? C2 C3 H3A 118.2 . . ? C3 C4 C5 117.2(3) . . ? C3 C4 C11 122.3(4) . . ? C5 C4 C11 120.5(3) . . ? C4 C5 C6 124.0(3) . . ? C4 C5 H5A 118.0 . . ? C6 C5 H5A 118.0 . . ? C5 C6 C1 117.5(3) . . ? C5 C6 C7 117.1(3) . . ? C1 C6 C7 125.4(3) . . ? C9 C7 C10 110.9(3) . . ? C9 C7 C8 105.4(3) . . ? C10 C7 C8 105.1(4) . . ? C9 C7 C6 111.5(3) . . ? C10 C7 C6 111.6(3) . . ? C8 C7 C6 112.0(3) . . ? 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 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C13' C11 C14 126.1(9) . . ? C13' C11 C4 116.2(5) . . ? C14 C11 C4 115.3(7) . . ? C13' C11 C14' 109.7(7) . . ? C14 C11 C14' 38.0(8) . . ? C4 C11 C14' 107.8(4) . . ? C13' C11 C12 59.6(7) . . ? C14 C11 C12 118.8(10) . . ? C4 C11 C12 105.4(5) . . ? C14' C11 C12 146.2(6) . . ? C13' C11 C12' 111.2(6) . . ? C14 C11 C12' 65.3(8) . . ? C4 C11 C12' 108.0(4) . . ? C14' C11 C12' 103.1(6) . . ? C12 C11 C12' 59.6(7) . . ? C13' C11 C13 42.2(6) . . ? C14 C11 C13 109.5(10) . . ? C4 C11 C13 104.5(6) . . ? C14' C11 C13 76.4(8) . . ? C12 C11 C13 101.6(9) . . ? C12' C11 C13 145.8(7) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C11 C12' H12D 109.5 . . ? C11 C12' H12E 109.5 . . ? H12D C12' H12E 109.5 . . ? C11 C12' H12F 109.5 . . ? H12D C12' H12F 109.5 . . ? H12E C12' H12F 109.5 . . ? C11 C13' H13D 109.5 . . ? C11 C13' H13E 109.5 . . ? H13D C13' H13E 109.5 . . ? C11 C13' H13F 109.5 . . ? H13D C13' H13F 109.5 . . ? H13E C13' H13F 109.5 . . ? C11 C14' H14D 109.5 . . ? C11 C14' H14E 109.5 . . ? H14D C14' H14E 109.5 . . ? C11 C14' H14F 109.5 . . ? H14D C14' H14F 109.5 . . ? H14E C14' H14F 109.5 . . ? C16 C15 C17 111.0(4) . . ? C16 C15 C18 107.0(4) . . ? C17 C15 C18 104.7(4) . . ? C16 C15 C2 110.7(3) . . ? C17 C15 C2 111.4(3) . . ? C18 C15 C2 111.8(3) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C28 120.1(3) . . ? C20 C19 P1 124.7(2) . . ? C28 C19 P1 115.2(3) . . ? C21 C20 C19 173.8(4) . . ? C20 C21 C22 174.9(4) . . ? C23 C22 C27 118.8(4) . . ? C23 C22 C21 119.5(3) . . ? C27 C22 C21 121.8(3) . . ? C22 C23 C24 120.4(4) . . ? C22 C23 H23A 119.8 . . ? C24 C23 H23A 119.8 . . ? C25 C24 C23 120.7(4) . . ? C25 C24 H24A 119.7 . . ? C23 C24 H24A 119.7 . . ? C26 C25 C24 120.0(4) . . ? C26 C25 H25A 120.0 . . ? C24 C25 H25A 120.0 . . ? C25 C26 C27 120.5(4) . . ? C25 C26 H26A 119.8 . . ? C27 C26 H26A 119.8 . . ? C22 C27 C26 119.6(4) . . ? C22 C27 H27A 120.2 . . ? C26 C27 H27A 120.2 . . ? C29 C28 C19 175.8(4) . . ? C28 C29 C29 178.7(5) . 3_567 ? 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 C19 P1 C1 C6 -94.3(3) . . . . ? C19 P1 C1 C2 89.6(3) . . . . ? C6 C1 C2 C3 3.7(5) . . . . ? P1 C1 C2 C3 179.8(2) . . . . ? C6 C1 C2 C15 -174.4(3) . . . . ? P1 C1 C2 C15 1.7(5) . . . . ? C1 C2 C3 C4 -0.8(5) . . . . ? C15 C2 C3 C4 177.5(3) . . . . ? C2 C3 C4 C5 -1.5(5) . . . . ? C2 C3 C4 C11 -178.0(3) . . . . ? C3 C4 C5 C6 0.9(5) . . . . ? C11 C4 C5 C6 177.5(3) . . . . ? C4 C5 C6 C1 2.0(5) . . . . ? C4 C5 C6 C7 -177.0(3) . . . . ? C2 C1 C6 C5 -4.3(5) . . . . ? P1 C1 C6 C5 179.6(2) . . . . ? C2 C1 C6 C7 174.7(3) . . . . ? P1 C1 C6 C7 -1.4(5) . . . . ? C5 C6 C7 C9 125.5(3) . . . . ? C1 C6 C7 C9 -53.4(4) . . . . ? C5 C6 C7 C10 -109.8(4) . . . . ? C1 C6 C7 C10 71.3(5) . . . . ? C5 C6 C7 C8 7.7(5) . . . . ? C1 C6 C7 C8 -171.2(3) . . . . ? C3 C4 C11 C13' -3.1(8) . . . . ? C5 C4 C11 C13' -179.6(7) . . . . ? C3 C4 C11 C14 -166.9(10) . . . . ? C5 C4 C11 C14 16.7(11) . . . . ? C3 C4 C11 C14' -126.7(6) . . . . ? C5 C4 C11 C14' 56.9(7) . . . . ? C3 C4 C11 C12 60.1(8) . . . . ? C5 C4 C11 C12 -116.3(8) . . . . ? C3 C4 C11 C12' 122.6(6) . . . . ? C5 C4 C11 C12' -53.8(6) . . . . ? C3 C4 C11 C13 -46.6(9) . . . . ? C5 C4 C11 C13 137.0(8) . . . . ? C3 C2 C15 C16 109.4(4) . . . . ? C1 C2 C15 C16 -72.5(5) . . . . ? C3 C2 C15 C17 -126.6(4) . . . . ? C1 C2 C15 C17 51.5(5) . . . . ? C3 C2 C15 C18 -9.8(5) . . . . ? C1 C2 C15 C18 168.3(3) . . . . ? C1 P1 C19 C20 3.5(4) . . . . ? C1 P1 C19 C28 -175.6(3) . . . . ? C28 C19 C20 C21 -180(100) . . . . ? P1 C19 C20 C21 1(4) . . . . ? C19 C20 C21 C22 2(8) . . . . ? C20 C21 C22 C23 4(5) . . . . ? C20 C21 C22 C27 -176(5) . . . . ? C27 C22 C23 C24 -1.2(6) . . . . ? C21 C22 C23 C24 178.6(4) . . . . ? C22 C23 C24 C25 0.8(7) . . . . ? C23 C24 C25 C26 0.2(8) . . . . ? C24 C25 C26 C27 -0.7(8) . . . . ? C23 C22 C27 C26 0.8(7) . . . . ? C21 C22 C27 C26 -179.1(4) . . . . ? C25 C26 C27 C22 0.1(8) . . . . ? C20 C19 C28 C29 -151(6) . . . . ? P1 C19 C28 C29 28(6) . . . . ? C19 C28 C29 C29 -25(29) . . . 3_567 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.217 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.042