# 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 #=============================================================================== _audit_creation_date 12-15-2003 # 1. SUBMISSION DETAILS loop_ _publ_author_name 'T. Cantat' 'N. Mezailles' 'N. Maigrot' 'L. Ricard' 'Le Floch,P.' _publ_contact_author_name 'Prof Pascal Le Floch' _publ_contact_author_address ; Chemistry CNRS Laboratoire "Heteroelemenst et Coor Palaiseau 91128 FRANCE ; _publ_contact_author_email LEFLOCH@POLY.POLYTECHNIQUE.FR _publ_section_title ; Titanocene and Zirconocene Complexes of a Phosphorus Analog of an Arduengo's Carbene: Application in the Synthesis of 1,3-Diphosphafulvenes. ; _publ_section_abstract ; ? ; _publ_section_comment ; ; _publ_section_exptl_prep ;All structures were solved using SIR97 (Altomare et al.) and refined with SHELXL97 (Sheldrick). Figures were drawn with Platon (Spek, 1990). ; _publ_section_references ;Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993) J. Appl. Cryst. 26, 343-350. Sheldrick, G.M. SHELXL97. Program for crystal structure refinement. University of Gottingen, Germany, 1997. Sluis, P. v.d., Spek, A.L. (1990). Acta Cryst. A46, 194-201. Spek, A.L. (1990). Acta Cryst. A46, C-34. ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; #=============================================================================== # If more than one structure is reported, sections 5-10 should be filled in # per structure. For each data set, replace the ? in the data_? line below # by a unique identifier. #=============================================================================== data_p2c4phi _database_code_depnum_ccdc_archive 'CCDC 227151' #compound 8b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H30 P2' _chemical_formula_weight 572.58 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 '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 11.7340(10) _cell_length_b 6.3270(10) _cell_length_c 40.956(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.3540(10) _cell_angle_gamma 90.00 _cell_volume 3039.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150.0(10) _cell_measurement_reflns_used 251 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 20.0 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.171 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9634 _exptl_absorpt_correction_T_max 0.9898 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150.0(10) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7293 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0511 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 23.25 _reflns_number_total 4288 _reflns_number_gt 3070 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0796P)^2^+2.5184P] 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 4288 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0843 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1561 _refine_ls_wR_factor_gt 0.1398 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 0.37346(8) -0.01221(15) 0.39107(2) 0.0370(3) Uani 1 1 d . . . P2 P 0.17102(8) 0.25525(15) 0.36655(2) 0.0373(3) Uani 1 1 d . . . C1 C 0.2720(4) 0.0874(6) 0.42135(10) 0.0517(10) Uani 1 1 d . . . C2 C 0.1823(4) 0.1883(6) 0.41062(10) 0.0533(11) Uani 1 1 d . . . C3 C 0.2910(4) 0.0855(6) 0.35564(10) 0.0549(11) Uani 1 1 d . . . C4 C 0.3151(4) 0.0288(6) 0.32588(10) 0.0541(11) Uani 1 1 d . . . C5 C 0.4137(3) -0.1181(6) 0.31802(8) 0.0397(9) Uani 1 1 d . . . C6 C 0.4893(3) -0.0532(7) 0.29432(9) 0.0520(11) Uani 1 1 d . . . H6 H 0.4833 0.0833 0.2848 0.062 Uiso 1 1 calc R . . C7 C 0.5761(3) -0.1972(9) 0.28473(10) 0.0694(15) Uani 1 1 d . . . H7 H 0.6294 -0.1581 0.2687 0.083 Uiso 1 1 calc R . . C8 C 0.5814(4) -0.3955(8) 0.29929(12) 0.0644(13) Uani 1 1 d . . . H8 H 0.6399 -0.4906 0.2933 0.077 Uiso 1 1 calc R . . C9 C 0.5065(4) -0.4563(8) 0.32153(11) 0.0610(12) Uani 1 1 d . . . H9 H 0.5112 -0.5936 0.3308 0.073 Uiso 1 1 calc R . . C10 C 0.4236(4) -0.3202(6) 0.33075(9) 0.0515(11) Uani 1 1 d . . . H10 H 0.3706 -0.3653 0.3465 0.062 Uiso 1 1 calc R . . C11 C 0.2419(3) 0.1004(6) 0.29632(9) 0.0431(9) Uani 1 1 d . . . C12 C 0.2107(3) 0.3079(6) 0.28999(9) 0.0464(10) Uani 1 1 d . . . H12 H 0.2341 0.4171 0.3046 0.056 Uiso 1 1 calc R . . C13 C 0.1455(3) 0.3561(7) 0.26241(10) 0.0519(11) Uani 1 1 d . . . H13 H 0.1238 0.4985 0.2583 0.062 Uiso 1 1 calc R . . C14 C 0.1117(3) 0.1996(7) 0.24094(9) 0.0523(11) Uani 1 1 d . . . H14 H 0.0665 0.2335 0.2221 0.063 Uiso 1 1 calc R . . C15 C 0.1433(3) -0.0044(7) 0.24686(9) 0.0482(10) Uani 1 1 d . . . H15 H 0.1201 -0.1129 0.2321 0.058 Uiso 1 1 calc R . . C16 C 0.2086(3) -0.0539(6) 0.27411(9) 0.0482(10) Uani 1 1 d . . . H16 H 0.2313 -0.1963 0.2778 0.058 Uiso 1 1 calc R . . C17 C 0.4889(3) 0.1836(6) 0.39605(8) 0.0371(9) Uani 1 1 d . . . C18 C 0.5990(3) 0.1222(7) 0.38813(9) 0.0475(10) Uani 1 1 d . . . H18 H 0.6120 -0.0149 0.3795 0.057 Uiso 1 1 calc R . . C19 C 0.6900(3) 0.2612(8) 0.39280(9) 0.0547(11) Uani 1 1 d . . . H19 H 0.7650 0.2179 0.3877 0.066 Uiso 1 1 calc R . . C20 C 0.6716(3) 0.4603(7) 0.40479(9) 0.0542(11) Uani 1 1 d . . . H20 H 0.7337 0.5552 0.4077 0.065 Uiso 1 1 calc R . . C21 C 0.5634(3) 0.5225(7) 0.41252(9) 0.0496(10) Uani 1 1 d . . . H21 H 0.5508 0.6601 0.4210 0.060 Uiso 1 1 calc R . . C22 C 0.4729(3) 0.3853(6) 0.40800(8) 0.0427(9) Uani 1 1 d . . . H22 H 0.3983 0.4304 0.4132 0.051 Uiso 1 1 calc R . . C23 C 0.2987(3) 0.0414(6) 0.45672(8) 0.0401(9) Uani 1 1 d . . . C24 C 0.3374(3) -0.1584(7) 0.46537(9) 0.0492(10) Uani 1 1 d . . . H24 H 0.3411 -0.2662 0.4493 0.059 Uiso 1 1 calc R . . C25 C 0.3711(3) -0.2021(7) 0.49771(11) 0.0554(12) Uani 1 1 d . . . H25 H 0.3980 -0.3388 0.5036 0.066 Uiso 1 1 calc R . . C26 C 0.3648(3) -0.0443(9) 0.52096(10) 0.0594(12) Uani 1 1 d . . . H26 H 0.3863 -0.0733 0.5430 0.071 Uiso 1 1 calc R . . C27 C 0.3282(3) 0.1506(8) 0.51248(10) 0.0581(12) Uani 1 1 d . . . H27 H 0.3253 0.2584 0.5286 0.070 Uiso 1 1 calc R . . C28 C 0.2953(3) 0.1949(6) 0.48091(9) 0.0449(10) Uani 1 1 d . . . H28 H 0.2697 0.3332 0.4755 0.054 Uiso 1 1 calc R . . C29 C 0.0858(3) 0.2578(6) 0.43194(9) 0.0415(9) Uani 1 1 d . . . C30 C 0.0273(3) 0.1149(6) 0.45127(9) 0.0479(10) Uani 1 1 d . . . H30 H 0.0516 -0.0282 0.4524 0.057 Uiso 1 1 calc R . . C31 C -0.0658(3) 0.1794(7) 0.46884(10) 0.0525(11) Uani 1 1 d . . . H31 H -0.1053 0.0808 0.4819 0.063 Uiso 1 1 calc R . . C32 C -0.1005(3) 0.3842(7) 0.46738(10) 0.0537(11) Uani 1 1 d . . . H32 H -0.1642 0.4287 0.4795 0.064 Uiso 1 1 calc R . . C33 C -0.0440(3) 0.5263(6) 0.44848(10) 0.0518(11) Uani 1 1 d . . . H33 H -0.0686 0.6693 0.4476 0.062 Uiso 1 1 calc R . . C34 C 0.0478(3) 0.4631(6) 0.43082(9) 0.0461(10) Uani 1 1 d . . . H34 H 0.0859 0.5630 0.4176 0.055 Uiso 1 1 calc R . . C35 C 0.0446(3) 0.0990(6) 0.35503(8) 0.0387(9) Uani 1 1 d . . . C36 C 0.0303(3) -0.1075(7) 0.36584(10) 0.0538(11) Uani 1 1 d . . . H36 H 0.0893 -0.1738 0.3784 0.065 Uiso 1 1 calc R . . C37 C -0.0692(4) -0.2177(7) 0.35850(10) 0.0606(12) Uani 1 1 d . . . H37 H -0.0783 -0.3579 0.3663 0.073 Uiso 1 1 calc R . . C38 C -0.1546(4) -0.1252(8) 0.34002(10) 0.0599(12) Uani 1 1 d . . . H38 H -0.2232 -0.2002 0.3354 0.072 Uiso 1 1 calc R . . C39 C -0.1406(3) 0.0770(8) 0.32819(10) 0.0574(12) Uani 1 1 d . . . H39 H -0.1986 0.1399 0.3148 0.069 Uiso 1 1 calc R . . C40 C -0.0420(3) 0.1882(7) 0.33579(9) 0.0481(10) Uani 1 1 d . . . H40 H -0.0333 0.3279 0.3277 0.058 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 0.0402(6) 0.0411(6) 0.0297(5) 0.0007(4) 0.0005(4) 0.0035(4) P2 0.0403(5) 0.0407(6) 0.0308(5) 0.0026(4) 0.0014(4) 0.0021(5) C1 0.059(3) 0.040(2) 0.055(3) 0.001(2) -0.005(2) -0.006(2) C2 0.053(3) 0.044(2) 0.062(3) -0.004(2) 0.000(2) -0.010(2) C3 0.064(3) 0.047(3) 0.053(3) -0.001(2) 0.003(2) -0.011(2) C4 0.060(3) 0.050(3) 0.053(3) -0.002(2) 0.007(2) -0.022(2) C5 0.039(2) 0.050(2) 0.030(2) -0.0004(18) 0.0037(16) 0.0037(18) C6 0.044(2) 0.076(3) 0.036(2) 0.002(2) -0.0020(18) -0.011(2) C7 0.038(2) 0.126(5) 0.045(3) -0.016(3) 0.015(2) -0.018(3) C8 0.053(3) 0.068(3) 0.072(3) -0.019(3) -0.010(2) 0.013(2) C9 0.064(3) 0.068(3) 0.050(3) -0.008(2) -0.012(2) 0.010(3) C10 0.070(3) 0.049(3) 0.036(2) -0.005(2) 0.002(2) 0.007(2) C11 0.047(2) 0.050(3) 0.033(2) 0.0080(19) -0.0016(17) -0.012(2) C12 0.054(2) 0.055(3) 0.030(2) 0.0009(19) 0.0045(19) -0.008(2) C13 0.045(2) 0.048(3) 0.063(3) 0.012(2) 0.006(2) -0.002(2) C14 0.044(2) 0.074(3) 0.038(2) 0.019(2) -0.0055(19) -0.005(2) C15 0.045(2) 0.064(3) 0.036(2) -0.005(2) -0.0048(18) -0.006(2) C16 0.044(2) 0.047(2) 0.052(3) 0.000(2) -0.006(2) -0.0001(19) C17 0.037(2) 0.050(2) 0.0244(18) 0.0059(17) -0.0019(15) 0.0044(17) C18 0.043(2) 0.061(3) 0.038(2) -0.006(2) 0.0017(18) 0.006(2) C19 0.036(2) 0.085(3) 0.044(2) -0.001(2) 0.0050(18) -0.001(2) C20 0.046(2) 0.073(3) 0.043(2) 0.000(2) -0.0044(19) -0.010(2) C21 0.048(2) 0.052(3) 0.048(2) -0.002(2) -0.0094(19) -0.004(2) C22 0.039(2) 0.051(3) 0.038(2) 0.0017(19) -0.0015(17) 0.0025(19) C23 0.047(2) 0.044(2) 0.029(2) 0.0016(18) -0.0010(16) -0.0022(18) C24 0.060(3) 0.050(3) 0.039(2) 0.004(2) 0.0128(19) 0.000(2) C25 0.036(2) 0.067(3) 0.063(3) 0.035(3) 0.005(2) 0.003(2) C26 0.046(2) 0.100(4) 0.033(2) 0.012(3) -0.0069(19) -0.015(3) C27 0.056(3) 0.083(3) 0.036(2) -0.009(2) 0.002(2) -0.013(2) C28 0.041(2) 0.052(3) 0.042(2) -0.006(2) -0.0001(18) -0.0004(18) C29 0.035(2) 0.048(3) 0.042(2) -0.0092(19) 0.0044(17) -0.0067(19) C30 0.043(2) 0.038(2) 0.062(3) 0.006(2) 0.001(2) 0.0009(19) C31 0.043(2) 0.059(3) 0.056(3) 0.009(2) 0.010(2) -0.009(2) C32 0.038(2) 0.066(3) 0.057(3) -0.011(2) 0.0089(19) 0.000(2) C33 0.050(2) 0.041(2) 0.064(3) -0.002(2) -0.002(2) 0.007(2) C34 0.055(2) 0.042(2) 0.042(2) 0.0048(19) 0.0068(19) -0.008(2) C35 0.040(2) 0.044(2) 0.032(2) -0.0025(17) 0.0013(17) 0.0048(18) C36 0.050(2) 0.052(3) 0.059(3) -0.002(2) -0.011(2) 0.002(2) C37 0.063(3) 0.056(3) 0.063(3) -0.002(2) 0.000(2) -0.009(2) C38 0.048(3) 0.081(4) 0.051(3) -0.020(3) 0.001(2) -0.011(2) C39 0.042(2) 0.086(4) 0.043(2) -0.004(2) -0.0061(19) 0.008(2) C40 0.051(2) 0.059(3) 0.034(2) 0.0008(19) 0.0009(19) 0.008(2) _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 C3 1.832(4) . ? P1 C17 1.843(4) . ? P1 C1 1.850(4) . ? P2 C3 1.834(4) . ? P2 C35 1.835(4) . ? P2 C2 1.856(4) . ? C1 C2 1.299(5) . ? C1 C23 1.504(5) . ? C2 C29 1.512(5) . ? C3 C4 1.308(5) . ? C4 C5 1.525(6) . ? C4 C11 1.536(6) . ? C5 C10 1.385(5) . ? C5 C6 1.392(5) . ? C6 C7 1.429(6) . ? C7 C8 1.390(7) . ? C8 C9 1.337(6) . ? C9 C10 1.360(6) . ? C11 C16 1.384(5) . ? C11 C12 1.386(5) . ? C12 C13 1.384(5) . ? C13 C14 1.377(6) . ? C14 C15 1.363(6) . ? C15 C16 1.375(5) . ? C17 C22 1.381(5) . ? C17 C18 1.395(5) . ? C18 C19 1.393(5) . ? C19 C20 1.371(6) . ? C20 C21 1.373(6) . ? C21 C22 1.381(5) . ? C23 C24 1.386(5) . ? C23 C28 1.389(5) . ? C24 C25 1.401(5) . ? C25 C26 1.383(6) . ? C26 C27 1.348(6) . ? C27 C28 1.370(5) . ? C29 C34 1.374(5) . ? C29 C30 1.393(5) . ? C30 C31 1.384(5) . ? C31 C32 1.359(6) . ? C32 C33 1.368(6) . ? C33 C34 1.372(5) . ? C35 C40 1.391(5) . ? C35 C36 1.391(5) . ? C36 C37 1.386(6) . ? C37 C38 1.373(6) . ? C38 C39 1.379(6) . ? C39 C40 1.384(5) . ? 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 C3 P1 C17 103.52(17) . . ? C3 P1 C1 94.56(19) . . ? C17 P1 C1 100.36(17) . . ? C3 P2 C35 104.01(17) . . ? C3 P2 C2 93.78(19) . . ? C35 P2 C2 99.53(17) . . ? C2 C1 C23 124.8(4) . . ? C2 C1 P1 118.0(3) . . ? C23 C1 P1 117.2(3) . . ? C1 C2 C29 124.0(4) . . ? C1 C2 P2 118.7(3) . . ? C29 C2 P2 117.3(3) . . ? C4 C3 P1 121.6(4) . . ? C4 C3 P2 124.9(4) . . ? P1 C3 P2 113.5(2) . . ? C3 C4 C5 123.1(4) . . ? C3 C4 C11 121.6(4) . . ? C5 C4 C11 115.2(3) . . ? C10 C5 C6 119.1(4) . . ? C10 C5 C4 122.7(3) . . ? C6 C5 C4 117.8(4) . . ? C5 C6 C7 118.3(4) . . ? C8 C7 C6 118.8(4) . . ? C9 C8 C7 121.9(4) . . ? C8 C9 C10 119.6(5) . . ? C9 C10 C5 122.3(4) . . ? C16 C11 C12 118.4(3) . . ? C16 C11 C4 117.0(3) . . ? C12 C11 C4 124.6(3) . . ? C13 C12 C11 120.0(4) . . ? C14 C13 C12 120.5(4) . . ? C15 C14 C13 119.6(4) . . ? C14 C15 C16 120.3(4) . . ? C15 C16 C11 121.0(4) . . ? C22 C17 C18 118.3(3) . . ? C22 C17 P1 123.7(3) . . ? C18 C17 P1 118.0(3) . . ? C19 C18 C17 120.2(4) . . ? C20 C19 C18 120.2(4) . . ? C19 C20 C21 120.0(4) . . ? C20 C21 C22 120.1(4) . . ? C21 C22 C17 121.2(4) . . ? C24 C23 C28 118.0(3) . . ? C24 C23 C1 118.8(3) . . ? C28 C23 C1 122.9(3) . . ? C23 C24 C25 120.3(4) . . ? C26 C25 C24 119.3(4) . . ? C27 C26 C25 120.3(4) . . ? C26 C27 C28 120.7(4) . . ? C27 C28 C23 121.2(4) . . ? C34 C29 C30 118.0(3) . . ? C34 C29 C2 120.1(3) . . ? C30 C29 C2 121.7(3) . . ? C31 C30 C29 120.6(4) . . ? C32 C31 C30 119.9(4) . . ? C31 C32 C33 120.2(4) . . ? C32 C33 C34 120.3(4) . . ? C33 C34 C29 121.0(4) . . ? C40 C35 C36 118.0(4) . . ? C40 C35 P2 120.2(3) . . ? C36 C35 P2 121.8(3) . . ? C37 C36 C35 120.7(4) . . ? C38 C37 C36 120.4(4) . . ? C37 C38 C39 119.8(4) . . ? C38 C39 C40 119.9(4) . . ? C39 C40 C35 121.1(4) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.633 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.049 #=========================================== data_p2c2adm _database_code_depnum_ccdc_archive 'CCDC 235099' #compound 6a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H36 Cl2 P2' _chemical_formula_weight 625.51 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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0670(10) _cell_length_b 12.3250(10) _cell_length_c 13.6690(10) _cell_angle_alpha 72.2200(10) _cell_angle_beta 77.5900(10) _cell_angle_gamma 80.8000(10) _cell_volume 1569.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150.0(10) _cell_measurement_reflns_used 251 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 20.0 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.336 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9359 _exptl_absorpt_correction_T_max 0.9482 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150.0(10) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14286 _diffrn_reflns_av_R_equivalents 0.0152 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 30.03 _reflns_number_total 9134 _reflns_number_gt 7563 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0539P)^2^+0.3901P] 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 SHELXL _refine_ls_extinction_coef 0.0047(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 9134 _refine_ls_number_parameters 380 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.1104 _refine_ls_wR_factor_gt 0.1040 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 Cl1 Cl 0.78104(5) 0.43510(4) 0.83670(4) 0.05620(13) Uani 1 1 d . . . Cl2 Cl 0.91123(6) 0.27166(4) 0.72326(4) 0.06181(14) Uani 1 1 d . . . P1 P 0.50389(3) 0.31218(2) 0.59836(2) 0.02024(8) Uani 1 1 d . . . P2 P 0.49486(3) 0.15280(2) 0.82077(2) 0.02060(8) Uani 1 1 d . . . C1 C 0.59600(12) 0.16944(10) 0.61420(9) 0.0202(2) Uani 1 1 d . . . C2 C 0.59622(12) 0.10122(10) 0.71262(9) 0.0203(2) Uani 1 1 d . . . C3 C 0.43454(12) 0.29023(10) 0.73794(9) 0.0209(2) Uani 1 1 d . . . C4 C 0.36625(13) 0.37574(10) 0.77661(9) 0.0231(2) Uani 1 1 d . . . C5 C 0.33808(15) 0.49726(10) 0.71133(10) 0.0282(3) Uani 1 1 d . . . H5 H 0.3764 0.5040 0.6361 0.034 Uiso 1 1 calc R . . C6 C 0.40675(17) 0.57595(11) 0.75003(11) 0.0342(3) Uani 1 1 d . . . H6A H 0.5067 0.5540 0.7414 0.041 Uiso 1 1 calc R . . H6B H 0.3906 0.6564 0.7079 0.041 Uiso 1 1 calc R . . C7 C 0.34804(16) 0.56557(12) 0.86532(11) 0.0342(3) Uani 1 1 d . . . H7 H 0.3921 0.6174 0.8897 0.041 Uiso 1 1 calc R . . C8 C 0.19311(17) 0.59909(12) 0.87852(12) 0.0368(3) Uani 1 1 d . . . H8A H 0.1549 0.5927 0.9529 0.044 Uiso 1 1 calc R . . H8B H 0.1740 0.6795 0.8376 0.044 Uiso 1 1 calc R . . C9 C 0.12546(15) 0.51996(12) 0.84094(11) 0.0338(3) Uani 1 1 d . . . H9 H 0.0245 0.5418 0.8501 0.041 Uiso 1 1 calc R . . C10 C 0.18290(16) 0.53148(12) 0.72537(11) 0.0348(3) Uani 1 1 d . . . H10A H 0.1638 0.6116 0.6835 0.042 Uiso 1 1 calc R . . H10B H 0.1383 0.4813 0.7006 0.042 Uiso 1 1 calc R . . C11 C 0.15473(15) 0.39550(12) 0.90476(11) 0.0312(3) Uani 1 1 d . . . H11A H 0.1106 0.3443 0.8808 0.037 Uiso 1 1 calc R . . H11B H 0.1162 0.3871 0.9794 0.037 Uiso 1 1 calc R . . C12 C 0.31022(14) 0.36120(11) 0.89160(10) 0.0260(2) Uani 1 1 d . . . H12 H 0.3297 0.2798 0.9326 0.031 Uiso 1 1 calc R . . C13 C 0.37727(15) 0.44095(12) 0.92967(11) 0.0313(3) Uani 1 1 d . . . H13A H 0.3403 0.4331 1.0044 0.038 Uiso 1 1 calc R . . H13B H 0.4772 0.4193 0.9219 0.038 Uiso 1 1 calc R . . C14 C 0.35168(12) 0.30539(10) 0.54725(9) 0.0213(2) Uani 1 1 d . . . C15 C 0.28978(14) 0.40838(10) 0.49058(10) 0.0257(2) Uani 1 1 d . . . H15 H 0.3315 0.4771 0.4745 0.031 Uiso 1 1 calc R . . C16 C 0.16772(14) 0.41100(11) 0.45755(10) 0.0295(3) Uani 1 1 d . . . H16 H 0.1253 0.4817 0.4205 0.035 Uiso 1 1 calc R . . C17 C 0.10779(14) 0.31085(12) 0.47856(11) 0.0316(3) Uani 1 1 d . . . H17 H 0.0246 0.3127 0.4556 0.038 Uiso 1 1 calc R . . C18 C 0.16961(14) 0.20785(11) 0.53323(11) 0.0298(3) Uani 1 1 d . . . H18 H 0.1294 0.1389 0.5466 0.036 Uiso 1 1 calc R . . C19 C 0.28975(13) 0.20501(10) 0.56844(10) 0.0246(2) Uani 1 1 d . . . H19 H 0.3302 0.1344 0.6072 0.029 Uiso 1 1 calc R . . C20 C 0.68417(12) 0.14334(9) 0.51973(9) 0.0210(2) Uani 1 1 d . . . C21 C 0.62727(13) 0.12933(11) 0.44050(9) 0.0254(2) Uani 1 1 d . . . H21 H 0.5307 0.1348 0.4472 0.030 Uiso 1 1 calc R . . C22 C 0.71055(15) 0.10733(11) 0.35153(10) 0.0287(3) Uani 1 1 d . . . H22 H 0.6707 0.0966 0.2986 0.034 Uiso 1 1 calc R . . C23 C 0.85141(14) 0.10113(11) 0.34049(10) 0.0290(3) Uani 1 1 d . . . H23 H 0.9083 0.0872 0.2795 0.035 Uiso 1 1 calc R . . C24 C 0.90902(14) 0.11525(12) 0.41858(11) 0.0307(3) Uani 1 1 d . . . H24 H 1.0056 0.1109 0.4112 0.037 Uiso 1 1 calc R . . C25 C 0.82598(13) 0.13582(11) 0.50780(10) 0.0274(3) Uani 1 1 d . . . H25 H 0.8664 0.1448 0.5612 0.033 Uiso 1 1 calc R . . C26 C 0.67222(12) -0.01416(10) 0.74183(9) 0.0222(2) Uani 1 1 d . . . C27 C 0.65576(15) -0.09843(11) 0.69823(10) 0.0289(3) Uani 1 1 d . . . H27 H 0.6020 -0.0799 0.6450 0.035 Uiso 1 1 calc R . . C28 C 0.71715(17) -0.20944(12) 0.73162(12) 0.0384(3) Uani 1 1 d . . . H28 H 0.7043 -0.2665 0.7019 0.046 Uiso 1 1 calc R . . C29 C 0.79683(17) -0.23675(12) 0.80802(12) 0.0403(4) Uani 1 1 d . . . H29 H 0.8393 -0.3125 0.8305 0.048 Uiso 1 1 calc R . . C30 C 0.81481(15) -0.15372(13) 0.85184(12) 0.0374(3) Uani 1 1 d . . . H30 H 0.8703 -0.1726 0.9040 0.045 Uiso 1 1 calc R . . C31 C 0.75211(14) -0.04295(11) 0.81996(11) 0.0292(3) Uani 1 1 d . . . H31 H 0.7635 0.0133 0.8512 0.035 Uiso 1 1 calc R . . C32 C 0.35611(13) 0.05921(10) 0.86111(9) 0.0232(2) Uani 1 1 d . . . C33 C 0.22320(14) 0.09681(11) 0.84307(10) 0.0283(3) Uani 1 1 d . . . H33 H 0.2010 0.1743 0.8061 0.034 Uiso 1 1 calc R . . C34 C 0.12256(15) 0.02119(13) 0.87904(12) 0.0357(3) Uani 1 1 d . . . H34 H 0.0317 0.0475 0.8676 0.043 Uiso 1 1 calc R . . C35 C 0.15515(17) -0.09253(13) 0.93155(11) 0.0377(3) Uani 1 1 d . . . H35 H 0.0867 -0.1441 0.9554 0.045 Uiso 1 1 calc R . . C36 C 0.28651(17) -0.13060(12) 0.94906(11) 0.0353(3) Uani 1 1 d . . . H36 H 0.3087 -0.2087 0.9841 0.042 Uiso 1 1 calc R . . C37 C 0.38669(15) -0.05543(11) 0.91575(10) 0.0286(3) Uani 1 1 d . . . H37 H 0.4764 -0.0818 0.9301 0.034 Uiso 1 1 calc R . . C38 C 0.75586(17) 0.33877(15) 0.77299(12) 0.0407(3) Uani 1 1 d . . . H38A H 0.7061 0.3802 0.7151 0.049 Uiso 1 1 calc R . . H38B H 0.6988 0.2799 0.8226 0.049 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 Cl1 0.0551(3) 0.0679(3) 0.0586(3) -0.0375(2) -0.0035(2) -0.0137(2) Cl2 0.0614(3) 0.0545(3) 0.0718(3) -0.0301(2) -0.0080(2) 0.0070(2) P1 0.02156(16) 0.01887(14) 0.02009(14) -0.00501(11) -0.00399(11) -0.00200(11) P2 0.02235(16) 0.01983(14) 0.01953(14) -0.00551(11) -0.00459(11) -0.00075(11) C1 0.0188(5) 0.0211(5) 0.0217(5) -0.0074(4) -0.0039(4) -0.0017(4) C2 0.0194(5) 0.0202(5) 0.0222(5) -0.0067(4) -0.0046(4) -0.0013(4) C3 0.0220(6) 0.0202(5) 0.0202(5) -0.0058(4) -0.0038(4) -0.0016(4) C4 0.0246(6) 0.0223(5) 0.0219(5) -0.0068(4) -0.0043(4) 0.0003(4) C5 0.0371(7) 0.0209(5) 0.0238(6) -0.0057(4) -0.0046(5) 0.0028(5) C6 0.0419(8) 0.0232(6) 0.0358(7) -0.0096(5) -0.0012(6) -0.0031(5) C7 0.0412(8) 0.0288(6) 0.0354(7) -0.0156(6) -0.0046(6) -0.0018(6) C8 0.0451(9) 0.0291(7) 0.0348(7) -0.0147(6) -0.0041(6) 0.0074(6) C9 0.0303(7) 0.0322(7) 0.0364(7) -0.0115(6) -0.0071(6) 0.0092(5) C10 0.0407(8) 0.0294(6) 0.0329(7) -0.0089(5) -0.0133(6) 0.0101(6) C11 0.0285(7) 0.0320(6) 0.0303(6) -0.0099(5) -0.0016(5) 0.0028(5) C12 0.0283(6) 0.0248(6) 0.0226(6) -0.0076(5) -0.0030(5) 0.0033(5) C13 0.0331(7) 0.0341(7) 0.0284(6) -0.0142(5) -0.0061(5) 0.0030(5) C14 0.0217(6) 0.0221(5) 0.0193(5) -0.0055(4) -0.0035(4) -0.0012(4) C15 0.0279(6) 0.0218(5) 0.0260(6) -0.0035(4) -0.0067(5) -0.0024(5) C16 0.0286(7) 0.0280(6) 0.0292(6) -0.0033(5) -0.0105(5) 0.0025(5) C17 0.0256(7) 0.0374(7) 0.0325(7) -0.0079(6) -0.0100(5) -0.0025(5) C18 0.0285(7) 0.0285(6) 0.0342(7) -0.0077(5) -0.0078(5) -0.0068(5) C19 0.0257(6) 0.0221(5) 0.0256(6) -0.0057(4) -0.0058(5) -0.0017(4) C20 0.0221(6) 0.0191(5) 0.0201(5) -0.0044(4) -0.0025(4) -0.0014(4) C21 0.0236(6) 0.0291(6) 0.0241(6) -0.0090(5) -0.0051(5) -0.0005(5) C22 0.0343(7) 0.0294(6) 0.0238(6) -0.0100(5) -0.0052(5) -0.0019(5) C23 0.0324(7) 0.0266(6) 0.0256(6) -0.0090(5) 0.0024(5) -0.0027(5) C24 0.0226(6) 0.0358(7) 0.0326(7) -0.0119(5) 0.0012(5) -0.0034(5) C25 0.0235(6) 0.0331(6) 0.0273(6) -0.0113(5) -0.0034(5) -0.0035(5) C26 0.0190(5) 0.0216(5) 0.0226(5) -0.0039(4) -0.0011(4) -0.0002(4) C27 0.0333(7) 0.0252(6) 0.0273(6) -0.0086(5) -0.0035(5) -0.0004(5) C28 0.0488(9) 0.0244(6) 0.0368(7) -0.0102(6) 0.0017(6) 0.0016(6) C29 0.0380(8) 0.0266(6) 0.0420(8) -0.0003(6) 0.0008(6) 0.0083(6) C30 0.0280(7) 0.0348(7) 0.0396(8) 0.0029(6) -0.0094(6) 0.0028(6) C31 0.0259(6) 0.0281(6) 0.0315(6) -0.0035(5) -0.0085(5) -0.0014(5) C32 0.0259(6) 0.0245(5) 0.0185(5) -0.0066(4) -0.0009(4) -0.0039(4) C33 0.0258(6) 0.0299(6) 0.0292(6) -0.0097(5) -0.0027(5) -0.0025(5) C34 0.0277(7) 0.0441(8) 0.0368(7) -0.0140(6) -0.0009(6) -0.0091(6) C35 0.0413(8) 0.0403(8) 0.0325(7) -0.0108(6) 0.0031(6) -0.0188(6) C36 0.0466(9) 0.0280(6) 0.0282(6) -0.0029(5) -0.0017(6) -0.0113(6) C37 0.0326(7) 0.0269(6) 0.0236(6) -0.0035(5) -0.0033(5) -0.0041(5) C38 0.0377(8) 0.0518(9) 0.0373(8) -0.0140(7) -0.0057(6) -0.0165(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 Cl1 C38 1.7478(16) . ? Cl2 C38 1.7508(18) . ? P1 C1 1.8258(12) . ? P1 C3 1.8367(12) . ? P1 C14 1.8384(12) . ? P2 C3 1.8207(12) . ? P2 C2 1.8300(12) . ? P2 C32 1.8388(13) . ? C1 C2 1.3515(16) . ? C1 C20 1.4929(16) . ? C2 C26 1.4845(16) . ? C3 C4 1.3473(16) . ? C4 C5 1.5088(16) . ? C4 C12 1.5166(17) . ? C5 C10 1.538(2) . ? C5 C6 1.544(2) . ? C6 C7 1.533(2) . ? C7 C8 1.534(2) . ? C7 C13 1.5366(19) . ? C8 C9 1.532(2) . ? C9 C10 1.532(2) . ? C9 C11 1.5328(19) . ? C11 C12 1.5412(19) . ? C12 C13 1.5388(19) . ? C14 C15 1.3976(17) . ? C14 C19 1.3977(16) . ? C15 C16 1.3898(18) . ? C16 C17 1.3846(19) . ? C17 C18 1.3875(19) . ? C18 C19 1.3863(18) . ? C20 C25 1.3929(18) . ? C20 C21 1.3941(17) . ? C21 C22 1.3949(17) . ? C22 C23 1.386(2) . ? C23 C24 1.385(2) . ? C24 C25 1.3904(18) . ? C26 C27 1.3916(17) . ? C26 C31 1.3999(18) . ? C27 C28 1.3899(19) . ? C28 C29 1.381(2) . ? C29 C30 1.385(2) . ? C30 C31 1.3898(19) . ? C32 C33 1.3927(18) . ? C32 C37 1.4015(17) . ? C33 C34 1.3946(19) . ? C34 C35 1.388(2) . ? C35 C36 1.377(2) . ? C36 C37 1.3880(19) . ? 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 C3 95.08(5) . . ? C1 P1 C14 104.62(5) . . ? C3 P1 C14 101.61(5) . . ? C3 P2 C2 94.90(5) . . ? C3 P2 C32 108.18(6) . . ? C2 P2 C32 99.84(5) . . ? C2 C1 C20 124.02(11) . . ? C2 C1 P1 117.45(9) . . ? C20 C1 P1 117.73(8) . . ? C1 C2 C26 125.53(11) . . ? C1 C2 P2 118.40(9) . . ? C26 C2 P2 116.06(8) . . ? C4 C3 P2 122.64(9) . . ? C4 C3 P1 122.37(9) . . ? P2 C3 P1 113.92(6) . . ? C3 C4 C5 124.23(11) . . ? C3 C4 C12 123.75(11) . . ? C5 C4 C12 112.02(10) . . ? C4 C5 C10 109.41(11) . . ? C4 C5 C6 107.98(11) . . ? C10 C5 C6 109.41(11) . . ? C7 C6 C5 109.97(12) . . ? C6 C7 C8 109.54(12) . . ? C6 C7 C13 108.88(11) . . ? C8 C7 C13 109.56(12) . . ? C9 C8 C7 109.69(11) . . ? C10 C9 C8 109.64(13) . . ? C10 C9 C11 109.26(11) . . ? C8 C9 C11 109.63(12) . . ? C9 C10 C5 109.44(11) . . ? C9 C11 C12 109.86(11) . . ? C4 C12 C13 109.04(11) . . ? C4 C12 C11 108.43(10) . . ? C13 C12 C11 109.09(10) . . ? C7 C13 C12 109.58(11) . . ? C15 C14 C19 118.75(11) . . ? C15 C14 P1 117.46(9) . . ? C19 C14 P1 123.62(9) . . ? C16 C15 C14 120.51(11) . . ? C17 C16 C15 120.16(12) . . ? C16 C17 C18 119.78(13) . . ? C19 C18 C17 120.35(12) . . ? C18 C19 C14 120.42(11) . . ? C25 C20 C21 118.58(11) . . ? C25 C20 C1 120.21(11) . . ? C21 C20 C1 121.18(11) . . ? C20 C21 C22 120.73(12) . . ? C23 C22 C21 119.94(12) . . ? C24 C23 C22 119.81(12) . . ? C23 C24 C25 120.21(13) . . ? C24 C25 C20 120.72(12) . . ? C27 C26 C31 118.87(11) . . ? C27 C26 C2 120.32(11) . . ? C31 C26 C2 120.59(11) . . ? C28 C27 C26 120.76(13) . . ? C29 C28 C27 119.96(14) . . ? C28 C29 C30 120.00(13) . . ? C29 C30 C31 120.37(14) . . ? C30 C31 C26 120.03(13) . . ? C33 C32 C37 118.94(12) . . ? C33 C32 P2 123.73(9) . . ? C37 C32 P2 117.30(10) . . ? C32 C33 C34 120.27(13) . . ? C35 C34 C33 120.02(14) . . ? C36 C35 C34 120.08(13) . . ? C35 C36 C37 120.35(13) . . ? C36 C37 C32 120.30(13) . . ? Cl1 C38 Cl2 111.57(9) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.388 _refine_diff_density_min -0.522 _refine_diff_density_rms 0.049 #============================================ data_p2xant _database_code_depnum_ccdc_archive 'CCDC 235100' #compound 9a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H28 O P2' _chemical_formula_weight 586.56 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' O O 0.0106 0.0060 '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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3240(10) _cell_length_b 17.4290(10) _cell_length_c 19.2460(10) _cell_angle_alpha 101.2400(10) _cell_angle_beta 96.9600(10) _cell_angle_gamma 98.7700(10) _cell_volume 2994.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150.0(10) _cell_measurement_reflns_used 251 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 20.0 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 0.178 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9687 _exptl_absorpt_correction_T_max 0.9859 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150.0(10) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16597 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0722 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 25.35 _reflns_number_total 10913 _reflns_number_gt 7270 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0451P)^2^+0.0000P] 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 10913 _refine_ls_number_parameters 775 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0788 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1065 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _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 -0.24159(6) 0.71824(3) 0.82412(3) 0.02763(15) Uani 1 1 d . . . P2 P -0.20920(6) 0.66590(3) 0.66649(3) 0.02635(15) Uani 1 1 d . . . P3 P 0.17345(6) 0.31765(3) 0.83438(3) 0.02677(15) Uani 1 1 d . . . P4 P 0.21248(6) 0.25797(3) 0.67857(3) 0.02744(15) Uani 1 1 d . . . O1 O -0.43490(17) 0.41754(7) 0.74746(8) 0.0337(4) Uani 1 1 d . . . O2 O 0.40423(16) 0.55393(7) 0.74044(7) 0.0304(4) Uani 1 1 d . . . C1 C -0.2619(2) 0.78828(11) 0.76640(11) 0.0270(5) Uani 1 1 d . . . C2 C -0.2512(2) 0.76528(11) 0.69641(11) 0.0264(5) Uani 1 1 d . . . C3 C -0.2090(2) 0.63842(11) 0.75303(10) 0.0264(5) Uani 1 1 d . . . C4 C -0.2362(2) 0.56033(11) 0.75847(11) 0.0266(5) Uani 1 1 d . . . C5 C -0.2738(2) 0.53414(11) 0.82294(11) 0.0284(5) Uani 1 1 d . . . C6 C -0.2181(3) 0.57520(12) 0.89347(12) 0.0345(6) Uani 1 1 d . . . H6 H -0.1446 0.6216 0.9016 0.041 Uiso 1 1 calc R . . C7 C -0.2673(3) 0.54994(13) 0.95139(12) 0.0409(6) Uani 1 1 d . . . H7 H -0.2275 0.5786 0.9988 0.049 Uiso 1 1 calc R . . C8 C -0.3751(3) 0.48264(13) 0.94041(13) 0.0433(6) Uani 1 1 d . . . H8 H -0.4105 0.4657 0.9802 0.052 Uiso 1 1 calc R . . C9 C -0.4310(3) 0.44021(12) 0.87166(13) 0.0373(6) Uani 1 1 d . . . H9 H -0.5059 0.3945 0.8639 0.045 Uiso 1 1 calc R . . C10 C -0.3775(2) 0.46460(11) 0.81454(12) 0.0306(5) Uani 1 1 d . . . C11 C -0.2477(2) 0.49230(11) 0.69668(11) 0.0280(5) Uani 1 1 d . . . C12 C -0.3545(2) 0.42495(11) 0.69301(12) 0.0304(5) Uani 1 1 d . . . C13 C -0.3905(3) 0.36408(11) 0.63238(12) 0.0352(6) Uani 1 1 d . . . H13 H -0.4688 0.3211 0.6292 0.042 Uiso 1 1 calc R . . C14 C -0.3117(3) 0.36664(12) 0.57693(12) 0.0387(6) Uani 1 1 d . . . H14 H -0.3369 0.3254 0.5348 0.046 Uiso 1 1 calc R . . C15 C -0.1960(3) 0.42820(11) 0.58126(12) 0.0344(6) Uani 1 1 d . . . H15 H -0.1381 0.4276 0.5438 0.041 Uiso 1 1 calc R . . C16 C -0.1653(3) 0.49090(11) 0.64082(11) 0.0319(6) Uani 1 1 d . . . H16 H -0.0867 0.5336 0.6436 0.038 Uiso 1 1 calc R . . C17 C -0.0611(2) 0.76613(11) 0.87807(11) 0.0286(5) Uani 1 1 d . . . C18 C -0.0478(3) 0.77664(11) 0.95217(11) 0.0328(6) Uani 1 1 d . . . H18 H -0.1297 0.7585 0.9734 0.039 Uiso 1 1 calc R . . C19 C 0.0842(3) 0.81345(12) 0.99519(12) 0.0370(6) Uani 1 1 d . . . H19 H 0.0925 0.8205 1.0458 0.044 Uiso 1 1 calc R . . C20 C 0.2031(3) 0.83982(12) 0.96502(13) 0.0403(6) Uani 1 1 d . . . H20 H 0.2935 0.8647 0.9948 0.048 Uiso 1 1 calc R . . C21 C 0.1920(3) 0.83040(12) 0.89157(13) 0.0416(6) Uani 1 1 d . . . H21 H 0.2747 0.8485 0.8708 0.050 Uiso 1 1 calc R . . C22 C 0.0597(3) 0.79444(12) 0.84817(12) 0.0353(6) Uani 1 1 d . . . H22 H 0.0514 0.7891 0.7977 0.042 Uiso 1 1 calc R . . C23 C -0.3059(3) 0.86468(11) 0.79998(11) 0.0287(5) Uani 1 1 d . . . C24 C -0.4493(3) 0.87623(12) 0.78680(12) 0.0367(6) Uani 1 1 d . . . H24 H -0.5209 0.8352 0.7559 0.044 Uiso 1 1 calc R . . C25 C -0.4908(3) 0.94677(13) 0.81793(12) 0.0401(6) Uani 1 1 d . . . H25 H -0.5896 0.9539 0.8080 0.048 Uiso 1 1 calc R . . C26 C -0.3880(3) 1.00603(13) 0.86309(13) 0.0447(7) Uani 1 1 d . . . H26 H -0.4155 1.0543 0.8848 0.054 Uiso 1 1 calc R . . C27 C -0.2457(3) 0.99526(13) 0.87665(13) 0.0498(7) Uani 1 1 d . . . H27 H -0.1747 1.0365 0.9076 0.060 Uiso 1 1 calc R . . C28 C -0.2040(3) 0.92537(12) 0.84610(12) 0.0406(6) Uani 1 1 d . . . H28 H -0.1050 0.9187 0.8566 0.049 Uiso 1 1 calc R . . C29 C -0.2745(2) 0.81351(11) 0.64159(11) 0.0258(5) Uani 1 1 d . . . C30 C -0.3560(2) 0.77898(12) 0.57385(11) 0.0307(5) Uani 1 1 d . . . H30 H -0.3959 0.7237 0.5624 0.037 Uiso 1 1 calc R . . C31 C -0.3794(3) 0.82416(13) 0.52337(12) 0.0366(6) Uani 1 1 d . . . H31 H -0.4367 0.8000 0.4779 0.044 Uiso 1 1 calc R . . C32 C -0.3199(3) 0.90419(12) 0.53856(12) 0.0356(6) Uani 1 1 d . . . H32 H -0.3370 0.9353 0.5040 0.043 Uiso 1 1 calc R . . C33 C -0.2354(3) 0.93861(12) 0.60445(12) 0.0368(6) Uani 1 1 d . . . H33 H -0.1921 0.9934 0.6149 0.044 Uiso 1 1 calc R . . C34 C -0.2135(3) 0.89390(11) 0.65497(11) 0.0327(6) Uani 1 1 d . . . H34 H -0.1554 0.9185 0.7001 0.039 Uiso 1 1 calc R . . C35 C -0.0161(2) 0.69343(10) 0.65534(11) 0.0255(5) Uani 1 1 d . . . C36 C 0.1014(2) 0.67392(11) 0.69644(11) 0.0298(5) Uani 1 1 d . . . H36 H 0.0833 0.6468 0.7337 0.036 Uiso 1 1 calc R . . C37 C 0.2431(3) 0.69340(12) 0.68368(12) 0.0346(6) Uani 1 1 d . . . H37 H 0.3219 0.6803 0.7126 0.041 Uiso 1 1 calc R . . C38 C 0.2715(3) 0.73191(12) 0.62913(12) 0.0377(6) Uani 1 1 d . . . H38 H 0.3694 0.7449 0.6204 0.045 Uiso 1 1 calc R . . C39 C 0.1571(3) 0.75133(12) 0.58747(12) 0.0361(6) Uani 1 1 d . . . H39 H 0.1763 0.7778 0.5500 0.043 Uiso 1 1 calc R . . C40 C 0.0154(3) 0.73240(11) 0.60018(11) 0.0310(5) Uani 1 1 d . . . H40 H -0.0626 0.7459 0.5711 0.037 Uiso 1 1 calc R . . C41 C 0.2339(2) 0.22190(11) 0.81132(11) 0.0270(5) Uani 1 1 d . . . C42 C 0.2403(2) 0.19317(11) 0.74161(11) 0.0267(5) Uani 1 1 d . . . C43 C 0.1750(2) 0.33988(11) 0.74501(11) 0.0268(5) Uani 1 1 d . . . C44 C 0.2004(2) 0.41593(11) 0.73510(11) 0.0266(5) Uani 1 1 d . . . C45 C 0.2103(2) 0.48746(11) 0.79276(11) 0.0259(5) Uani 1 1 d . . . C46 C 0.1229(3) 0.49420(12) 0.84602(12) 0.0324(6) Uani 1 1 d . . . H46 H 0.0436 0.4523 0.8444 0.039 Uiso 1 1 calc R . . C47 C 0.1484(3) 0.56090(12) 0.90170(12) 0.0384(6) Uani 1 1 d . . . H47 H 0.0880 0.5644 0.9381 0.046 Uiso 1 1 calc R . . C48 C 0.2636(3) 0.62270(12) 0.90355(12) 0.0420(6) Uani 1 1 d . . . H48 H 0.2835 0.6678 0.9423 0.050 Uiso 1 1 calc R . . C49 C 0.3481(3) 0.61919(12) 0.85038(12) 0.0365(6) Uani 1 1 d . . . H49 H 0.4260 0.6618 0.8518 0.044 Uiso 1 1 calc R . . C50 C 0.3194(2) 0.55266(11) 0.79408(11) 0.0287(5) Uani 1 1 d . . . C51 C 0.2386(2) 0.43716(11) 0.66844(11) 0.0257(5) Uani 1 1 d . . . C52 C 0.1791(3) 0.39407(12) 0.59913(11) 0.0337(6) Uani 1 1 d . . . H52 H 0.1034 0.3490 0.5928 0.040 Uiso 1 1 calc R . . C53 C 0.2282(3) 0.41575(13) 0.54003(12) 0.0380(6) Uani 1 1 d . . . H53 H 0.1855 0.3860 0.4934 0.046 Uiso 1 1 calc R . . C54 C 0.3394(3) 0.48068(12) 0.54808(12) 0.0370(6) Uani 1 1 d . . . H54 H 0.3751 0.4943 0.5071 0.044 Uiso 1 1 calc R . . C55 C 0.3984(2) 0.52558(12) 0.61559(11) 0.0315(5) Uani 1 1 d . . . H55 H 0.4750 0.5701 0.6215 0.038 Uiso 1 1 calc R . . C56 C 0.3448(2) 0.50491(11) 0.67416(11) 0.0283(5) Uani 1 1 d . . . C57 C -0.0195(2) 0.27796(11) 0.83989(11) 0.0279(5) Uani 1 1 d . . . C58 C -0.0942(3) 0.32224(12) 0.88660(12) 0.0357(6) Uani 1 1 d . . . H58 H -0.0453 0.3722 0.9155 0.043 Uiso 1 1 calc R . . C59 C -0.2393(3) 0.29421(14) 0.89148(13) 0.0427(6) Uani 1 1 d . . . H59 H -0.2895 0.3254 0.9231 0.051 Uiso 1 1 calc R . . C60 C -0.3110(3) 0.22168(14) 0.85086(13) 0.0427(6) Uani 1 1 d . . . H60 H -0.4107 0.2030 0.8539 0.051 Uiso 1 1 calc R . . C61 C -0.2376(3) 0.17612(13) 0.80578(12) 0.0365(6) Uani 1 1 d . . . H61 H -0.2862 0.1254 0.7784 0.044 Uiso 1 1 calc R . . C62 C -0.0936(2) 0.20375(12) 0.80016(11) 0.0298(5) Uani 1 1 d . . . H62 H -0.0441 0.1718 0.7688 0.036 Uiso 1 1 calc R . . C63 C 0.0332(2) 0.20563(11) 0.62591(10) 0.0272(5) Uani 1 1 d . . . C64 C 0.0350(3) 0.14154(11) 0.56954(11) 0.0320(5) Uani 1 1 d . . . H64 H 0.1259 0.1270 0.5599 0.038 Uiso 1 1 calc R . . C65 C -0.0947(3) 0.09941(12) 0.52781(11) 0.0357(6) Uani 1 1 d . . . H65 H -0.0924 0.0564 0.4894 0.043 Uiso 1 1 calc R . . C66 C -0.2272(3) 0.11960(12) 0.54173(12) 0.0354(6) Uani 1 1 d . . . H66 H -0.3163 0.0897 0.5137 0.042 Uiso 1 1 calc R . . C67 C -0.2302(3) 0.18352(12) 0.59657(11) 0.0329(6) Uani 1 1 d . . . H67 H -0.3214 0.1979 0.6059 0.039 Uiso 1 1 calc R . . C68 C -0.1003(3) 0.22662(12) 0.63788(11) 0.0310(5) Uani 1 1 d . . . H68 H -0.1030 0.2711 0.6748 0.037 Uiso 1 1 calc R . . C69 C 0.2847(2) 0.11622(11) 0.71020(11) 0.0288(5) Uani 1 1 d . . . C70 C 0.1866(3) 0.04475(12) 0.69632(12) 0.0372(6) Uani 1 1 d . . . H70 H 0.0906 0.0442 0.7082 0.045 Uiso 1 1 calc R . . C71 C 0.2270(3) -0.02595(13) 0.66525(12) 0.0428(7) Uani 1 1 d . . . H71 H 0.1591 -0.0746 0.6566 0.051 Uiso 1 1 calc R . . C72 C 0.3648(3) -0.02582(13) 0.64708(12) 0.0430(7) Uani 1 1 d . . . H72 H 0.3931 -0.0743 0.6265 0.052 Uiso 1 1 calc R . . C73 C 0.4622(3) 0.04531(13) 0.65886(12) 0.0419(6) Uani 1 1 d . . . H73 H 0.5573 0.0459 0.6458 0.050 Uiso 1 1 calc R . . C74 C 0.4213(3) 0.11554(12) 0.68963(11) 0.0340(6) Uani 1 1 d . . . H74 H 0.4884 0.1642 0.6968 0.041 Uiso 1 1 calc R . . C75 C 0.2716(2) 0.18487(11) 0.87323(11) 0.0293(5) Uani 1 1 d . . . C76 C 0.3669(2) 0.23044(13) 0.93376(11) 0.0353(6) Uani 1 1 d . . . H76 H 0.4049 0.2845 0.9350 0.042 Uiso 1 1 calc R . . C77 C 0.4072(3) 0.19845(15) 0.99198(12) 0.0429(6) Uani 1 1 d . . . H77 H 0.4727 0.2305 1.0324 0.051 Uiso 1 1 calc R . . C78 C 0.3529(3) 0.12084(15) 0.99147(13) 0.0487(7) Uani 1 1 d . . . H78 H 0.3819 0.0985 1.0310 0.058 Uiso 1 1 calc R . . C79 C 0.2558(3) 0.07535(14) 0.93305(14) 0.0531(7) Uani 1 1 d . . . H79 H 0.2164 0.0217 0.9329 0.064 Uiso 1 1 calc R . . C80 C 0.2154(3) 0.10673(12) 0.87483(13) 0.0436(7) Uani 1 1 d . . . H80 H 0.1481 0.0745 0.8351 0.052 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 0.0322(4) 0.0260(3) 0.0234(3) 0.0050(2) 0.0048(3) 0.0015(2) P2 0.0310(4) 0.0232(3) 0.0239(3) 0.0053(2) 0.0049(3) 0.0015(2) P3 0.0306(4) 0.0247(3) 0.0246(3) 0.0043(2) 0.0066(3) 0.0034(2) P4 0.0296(4) 0.0260(3) 0.0253(3) 0.0035(2) 0.0064(3) 0.0018(2) O1 0.0364(10) 0.0285(8) 0.0359(9) 0.0099(7) 0.0073(8) -0.0001(7) O2 0.0337(9) 0.0267(7) 0.0284(8) 0.0054(6) 0.0038(7) -0.0002(6) C1 0.0268(13) 0.0242(11) 0.0276(12) 0.0047(9) 0.0026(10) -0.0001(9) C2 0.0257(13) 0.0252(11) 0.0260(12) 0.0058(9) 0.0014(10) -0.0007(9) C3 0.0267(13) 0.0254(11) 0.0249(12) 0.0038(9) 0.0039(10) 0.0000(9) C4 0.0218(13) 0.0283(11) 0.0286(12) 0.0060(9) 0.0029(10) 0.0027(9) C5 0.0301(14) 0.0286(11) 0.0290(12) 0.0107(9) 0.0034(10) 0.0081(10) C6 0.0420(16) 0.0311(12) 0.0327(13) 0.0114(10) 0.0041(11) 0.0091(10) C7 0.0534(18) 0.0418(14) 0.0316(14) 0.0128(11) 0.0063(12) 0.0150(12) C8 0.0532(18) 0.0482(15) 0.0410(15) 0.0231(12) 0.0204(13) 0.0201(13) C9 0.0352(15) 0.0356(13) 0.0470(15) 0.0206(11) 0.0115(12) 0.0048(10) C10 0.0311(14) 0.0285(12) 0.0354(13) 0.0117(10) 0.0059(11) 0.0083(10) C11 0.0292(14) 0.0248(11) 0.0305(13) 0.0087(9) 0.0025(10) 0.0046(9) C12 0.0332(14) 0.0257(11) 0.0351(13) 0.0112(10) 0.0062(11) 0.0077(10) C13 0.0403(16) 0.0200(11) 0.0424(15) 0.0033(10) 0.0023(12) 0.0038(10) C14 0.0514(17) 0.0270(12) 0.0335(14) -0.0014(10) 0.0006(12) 0.0088(11) C15 0.0436(16) 0.0301(12) 0.0329(13) 0.0070(10) 0.0101(11) 0.0135(11) C16 0.0355(15) 0.0263(11) 0.0359(13) 0.0096(10) 0.0079(11) 0.0057(10) C17 0.0345(14) 0.0237(11) 0.0266(12) 0.0036(9) 0.0042(10) 0.0043(9) C18 0.0407(15) 0.0284(11) 0.0282(13) 0.0045(9) 0.0052(11) 0.0048(10) C19 0.0478(17) 0.0307(12) 0.0285(13) 0.0017(10) -0.0014(12) 0.0065(11) C20 0.0363(16) 0.0342(13) 0.0415(15) -0.0031(11) -0.0071(12) 0.0037(11) C21 0.0367(16) 0.0356(13) 0.0469(16) -0.0001(11) 0.0097(12) -0.0020(11) C22 0.0395(16) 0.0333(12) 0.0297(13) 0.0017(10) 0.0076(11) 0.0016(11) C23 0.0356(15) 0.0248(11) 0.0267(12) 0.0062(9) 0.0075(10) 0.0055(10) C24 0.0427(17) 0.0319(12) 0.0333(13) 0.0047(10) 0.0042(11) 0.0048(11) C25 0.0449(17) 0.0407(14) 0.0402(14) 0.0124(11) 0.0110(12) 0.0166(12) C26 0.070(2) 0.0298(13) 0.0398(15) 0.0089(11) 0.0170(14) 0.0175(13) C27 0.066(2) 0.0293(13) 0.0471(16) -0.0042(11) 0.0045(14) 0.0052(13) C28 0.0458(17) 0.0298(12) 0.0418(14) 0.0025(11) 0.0030(12) 0.0029(11) C29 0.0251(13) 0.0291(11) 0.0257(12) 0.0078(9) 0.0088(10) 0.0060(9) C30 0.0295(14) 0.0301(11) 0.0333(13) 0.0086(10) 0.0042(10) 0.0058(9) C31 0.0329(15) 0.0456(14) 0.0319(13) 0.0100(11) 0.0018(11) 0.0095(11) C32 0.0430(16) 0.0374(13) 0.0357(14) 0.0180(10) 0.0132(12) 0.0171(11) C33 0.0473(16) 0.0300(12) 0.0384(14) 0.0127(10) 0.0140(12) 0.0109(11) C34 0.0396(15) 0.0294(12) 0.0295(13) 0.0064(10) 0.0078(11) 0.0052(10) C35 0.0323(14) 0.0202(10) 0.0227(11) 0.0016(8) 0.0067(10) 0.0024(9) C36 0.0365(15) 0.0261(11) 0.0271(12) 0.0073(9) 0.0073(11) 0.0031(10) C37 0.0322(15) 0.0309(12) 0.0394(14) 0.0057(10) 0.0060(11) 0.0046(10) C38 0.0331(15) 0.0329(12) 0.0485(15) 0.0068(11) 0.0191(12) 0.0033(10) C39 0.0448(17) 0.0302(12) 0.0381(14) 0.0128(10) 0.0162(12) 0.0070(11) C40 0.0377(15) 0.0278(11) 0.0295(13) 0.0077(9) 0.0092(11) 0.0071(10) C41 0.0251(13) 0.0253(11) 0.0296(12) 0.0063(9) 0.0050(10) 0.0008(9) C42 0.0241(13) 0.0246(11) 0.0297(12) 0.0043(9) 0.0031(10) 0.0020(9) C43 0.0242(13) 0.0275(11) 0.0272(12) 0.0046(9) 0.0048(10) 0.0007(9) C44 0.0216(13) 0.0293(11) 0.0275(12) 0.0062(9) 0.0031(10) 0.0007(9) C45 0.0280(13) 0.0245(11) 0.0262(12) 0.0064(9) 0.0037(10) 0.0071(9) C46 0.0343(15) 0.0289(12) 0.0360(13) 0.0091(10) 0.0066(11) 0.0079(10) C47 0.0476(17) 0.0374(13) 0.0341(14) 0.0076(11) 0.0133(12) 0.0143(12) C48 0.0612(19) 0.0299(13) 0.0308(14) -0.0011(10) 0.0077(13) 0.0052(12) C49 0.0466(16) 0.0227(11) 0.0346(14) 0.0025(10) 0.0001(12) -0.0016(10) C50 0.0304(14) 0.0285(12) 0.0299(13) 0.0106(10) 0.0058(11) 0.0074(10) C51 0.0264(13) 0.0266(11) 0.0252(12) 0.0066(9) 0.0056(10) 0.0056(9) C52 0.0394(15) 0.0303(12) 0.0298(13) 0.0064(10) 0.0041(11) 0.0023(10) C53 0.0469(17) 0.0408(13) 0.0238(13) 0.0049(10) 0.0032(11) 0.0050(11) C54 0.0409(16) 0.0463(14) 0.0301(13) 0.0176(11) 0.0104(11) 0.0111(11) C55 0.0320(14) 0.0316(12) 0.0348(13) 0.0138(10) 0.0091(11) 0.0058(10) C56 0.0310(14) 0.0262(11) 0.0278(12) 0.0064(9) 0.0022(10) 0.0063(10) C57 0.0315(14) 0.0301(12) 0.0262(12) 0.0118(9) 0.0081(10) 0.0081(10) C58 0.0420(16) 0.0351(12) 0.0370(14) 0.0137(10) 0.0159(12) 0.0134(11) C59 0.0446(17) 0.0508(15) 0.0482(16) 0.0242(12) 0.0242(13) 0.0261(13) C60 0.0310(15) 0.0570(16) 0.0477(16) 0.0247(13) 0.0121(12) 0.0096(12) C61 0.0317(15) 0.0440(13) 0.0338(13) 0.0124(11) 0.0034(11) 0.0031(11) C62 0.0299(14) 0.0357(12) 0.0264(12) 0.0091(10) 0.0100(10) 0.0064(10) C63 0.0350(15) 0.0260(11) 0.0202(11) 0.0070(9) 0.0044(10) 0.0012(10) C64 0.0374(15) 0.0317(12) 0.0273(12) 0.0063(10) 0.0072(11) 0.0061(10) C65 0.0494(17) 0.0267(12) 0.0281(13) 0.0033(9) 0.0019(12) 0.0049(11) C66 0.0422(17) 0.0271(12) 0.0326(13) 0.0113(10) -0.0051(11) -0.0041(11) C67 0.0316(14) 0.0356(12) 0.0341(13) 0.0158(10) 0.0039(11) 0.0045(10) C68 0.0367(15) 0.0304(11) 0.0264(12) 0.0082(9) 0.0049(11) 0.0050(10) C69 0.0315(14) 0.0298(12) 0.0226(12) 0.0019(9) -0.0004(10) 0.0068(10) C70 0.0360(15) 0.0338(13) 0.0389(14) 0.0028(10) 0.0041(11) 0.0049(11) C71 0.0552(19) 0.0292(13) 0.0373(14) -0.0007(10) -0.0001(13) 0.0036(12) C72 0.062(2) 0.0376(14) 0.0299(14) -0.0004(10) 0.0050(13) 0.0234(13) C73 0.0443(17) 0.0505(15) 0.0347(14) 0.0051(11) 0.0112(12) 0.0219(13) C74 0.0344(15) 0.0351(12) 0.0316(13) 0.0038(10) 0.0053(11) 0.0079(10) C75 0.0298(14) 0.0328(12) 0.0281(12) 0.0073(9) 0.0083(10) 0.0101(10) C76 0.0298(14) 0.0465(13) 0.0311(13) 0.0123(11) 0.0074(11) 0.0045(11) C77 0.0377(16) 0.0633(16) 0.0310(14) 0.0150(12) 0.0078(11) 0.0117(12) C78 0.0547(19) 0.0660(17) 0.0380(15) 0.0230(13) 0.0130(13) 0.0305(14) C79 0.080(2) 0.0414(14) 0.0490(17) 0.0209(13) 0.0188(15) 0.0248(14) C80 0.0557(18) 0.0343(13) 0.0405(15) 0.0085(11) 0.0053(13) 0.0090(12) _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 1.819(2) . ? P1 C3 1.840(2) . ? P1 C17 1.849(2) . ? P2 C3 1.820(2) . ? P2 C2 1.833(2) . ? P2 C35 1.841(2) . ? P3 C41 1.833(2) . ? P3 C43 1.836(2) . ? P3 C57 1.850(2) . ? P4 C43 1.829(2) . ? P4 C42 1.834(2) . ? P4 C63 1.849(2) . ? O1 C12 1.375(3) . ? O1 C10 1.383(2) . ? O2 C50 1.376(3) . ? O2 C56 1.387(2) . ? C1 C2 1.349(3) . ? C1 C23 1.502(3) . ? C2 C29 1.487(3) . ? C3 C4 1.373(3) . ? C4 C5 1.466(3) . ? C4 C11 1.487(3) . ? C5 C10 1.400(3) . ? C5 C6 1.400(3) . ? C6 C7 1.379(3) . ? C7 C8 1.387(3) . ? C8 C9 1.379(3) . ? C9 C10 1.374(3) . ? C11 C16 1.394(3) . ? C11 C12 1.403(3) . ? C12 C13 1.383(3) . ? C13 C14 1.371(3) . ? C14 C15 1.383(3) . ? C15 C16 1.388(3) . ? C17 C18 1.390(3) . ? C17 C22 1.393(3) . ? C18 C19 1.385(3) . ? C19 C20 1.372(3) . ? C20 C21 1.380(3) . ? C21 C22 1.387(3) . ? C23 C24 1.383(3) . ? C23 C28 1.390(3) . ? C24 C25 1.391(3) . ? C25 C26 1.374(3) . ? C26 C27 1.368(4) . ? C27 C28 1.379(3) . ? C29 C34 1.390(3) . ? C29 C30 1.398(3) . ? C30 C31 1.382(3) . ? C31 C32 1.380(3) . ? C32 C33 1.381(3) . ? C33 C34 1.375(3) . ? C35 C36 1.396(3) . ? C35 C40 1.403(3) . ? C36 C37 1.376(3) . ? C37 C38 1.382(3) . ? C38 C39 1.380(3) . ? C39 C40 1.376(3) . ? C41 C42 1.349(3) . ? C41 C75 1.492(3) . ? C42 C69 1.499(3) . ? C43 C44 1.365(3) . ? C44 C51 1.472(3) . ? C44 C45 1.481(3) . ? C45 C46 1.384(3) . ? C45 C50 1.399(3) . ? C46 C47 1.387(3) . ? C47 C48 1.392(3) . ? C48 C49 1.363(3) . ? C49 C50 1.391(3) . ? C51 C56 1.397(3) . ? C51 C52 1.398(3) . ? C52 C53 1.374(3) . ? C53 C54 1.384(3) . ? C54 C55 1.379(3) . ? C55 C56 1.375(3) . ? C57 C58 1.391(3) . ? C57 C62 1.396(3) . ? C58 C59 1.388(3) . ? C59 C60 1.373(3) . ? C60 C61 1.376(3) . ? C61 C62 1.380(3) . ? C63 C68 1.382(3) . ? C63 C64 1.401(3) . ? C64 C65 1.382(3) . ? C65 C66 1.378(3) . ? C66 C67 1.383(3) . ? C67 C68 1.385(3) . ? C69 C74 1.380(3) . ? C69 C70 1.387(3) . ? C70 C71 1.388(3) . ? C71 C72 1.372(4) . ? C72 C73 1.382(3) . ? C73 C74 1.382(3) . ? C75 C80 1.390(3) . ? C75 C76 1.397(3) . ? C76 C77 1.383(3) . ? C77 C78 1.368(3) . ? C78 C79 1.378(3) . ? C79 C80 1.377(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 C1 P1 C3 95.12(9) . . ? C1 P1 C17 99.55(9) . . ? C3 P1 C17 107.22(10) . . ? C3 P2 C2 95.67(9) . . ? C3 P2 C35 107.21(10) . . ? C2 P2 C35 99.60(9) . . ? C41 P3 C43 95.33(9) . . ? C41 P3 C57 97.36(9) . . ? C43 P3 C57 106.84(9) . . ? C43 P4 C42 95.36(9) . . ? C43 P4 C63 106.73(10) . . ? C42 P4 C63 100.45(9) . . ? C12 O1 C10 117.04(17) . . ? C50 O2 C56 116.50(16) . . ? C2 C1 C23 125.12(19) . . ? C2 C1 P1 118.60(16) . . ? C23 C1 P1 115.92(15) . . ? C1 C2 C29 125.06(19) . . ? C1 C2 P2 117.22(16) . . ? C29 C2 P2 117.71(15) . . ? C4 C3 P2 121.63(15) . . ? C4 C3 P1 121.02(16) . . ? P2 C3 P1 113.33(10) . . ? C3 C4 C5 124.19(18) . . ? C3 C4 C11 123.34(19) . . ? C5 C4 C11 112.11(16) . . ? C10 C5 C6 116.5(2) . . ? C10 C5 C4 118.44(18) . . ? C6 C5 C4 124.98(18) . . ? C7 C6 C5 121.6(2) . . ? C6 C7 C8 119.9(2) . . ? C9 C8 C7 120.0(2) . . ? C10 C9 C8 119.5(2) . . ? C9 C10 O1 116.19(18) . . ? C9 C10 C5 122.4(2) . . ? O1 C10 C5 121.4(2) . . ? C16 C11 C12 117.28(19) . . ? C16 C11 C4 125.55(18) . . ? C12 C11 C4 117.1(2) . . ? O1 C12 C13 116.14(19) . . ? O1 C12 C11 122.21(18) . . ? C13 C12 C11 121.6(2) . . ? C14 C13 C12 119.1(2) . . ? C13 C14 C15 121.1(2) . . ? C14 C15 C16 119.3(2) . . ? C15 C16 C11 121.1(2) . . ? C18 C17 C22 118.8(2) . . ? C18 C17 P1 117.96(18) . . ? C22 C17 P1 123.17(16) . . ? C19 C18 C17 120.3(2) . . ? C20 C19 C18 120.3(2) . . ? C19 C20 C21 120.3(2) . . ? C20 C21 C22 119.7(2) . . ? C21 C22 C17 120.5(2) . . ? C24 C23 C28 118.1(2) . . ? C24 C23 C1 121.00(17) . . ? C28 C23 C1 120.9(2) . . ? C23 C24 C25 121.2(2) . . ? C26 C25 C24 119.6(2) . . ? C27 C26 C25 119.7(2) . . ? C26 C27 C28 121.0(2) . . ? C27 C28 C23 120.4(2) . . ? C34 C29 C30 117.47(19) . . ? C34 C29 C2 121.54(17) . . ? C30 C29 C2 120.97(17) . . ? C31 C30 C29 120.88(19) . . ? C32 C31 C30 120.4(2) . . ? C31 C32 C33 119.4(2) . . ? C34 C33 C32 120.2(2) . . ? C33 C34 C29 121.59(19) . . ? C36 C35 C40 117.7(2) . . ? C36 C35 P2 123.54(16) . . ? C40 C35 P2 118.69(16) . . ? C37 C36 C35 120.9(2) . . ? C36 C37 C38 120.5(2) . . ? C39 C38 C37 119.7(2) . . ? C40 C39 C38 120.1(2) . . ? C39 C40 C35 121.2(2) . . ? C42 C41 C75 127.49(19) . . ? C42 C41 P3 117.41(16) . . ? C75 C41 P3 115.10(15) . . ? C41 C42 C69 126.84(19) . . ? C41 C42 P4 117.95(15) . . ? C69 C42 P4 114.84(15) . . ? C44 C43 P4 120.38(17) . . ? C44 C43 P3 122.23(15) . . ? P4 C43 P3 113.27(11) . . ? C43 C44 C51 124.05(18) . . ? C43 C44 C45 123.93(19) . . ? C51 C44 C45 111.65(16) . . ? C46 C45 C50 117.65(18) . . ? C46 C45 C44 125.33(18) . . ? C50 C45 C44 117.0(2) . . ? C45 C46 C47 121.4(2) . . ? C46 C47 C48 119.2(2) . . ? C49 C48 C47 120.7(2) . . ? C48 C49 C50 119.4(2) . . ? O2 C50 C49 116.83(19) . . ? O2 C50 C45 121.87(17) . . ? C49 C50 C45 121.3(2) . . ? C56 C51 C52 116.7(2) . . ? C56 C51 C44 117.99(17) . . ? C52 C51 C44 125.25(18) . . ? C53 C52 C51 121.1(2) . . ? C52 C53 C54 120.4(2) . . ? C55 C54 C53 120.0(2) . . ? C56 C55 C54 119.0(2) . . ? C55 C56 O2 116.55(18) . . ? C55 C56 C51 122.49(18) . . ? O2 C56 C51 120.94(19) . . ? C58 C57 C62 117.9(2) . . ? C58 C57 P3 119.39(16) . . ? C62 C57 P3 122.69(17) . . ? C59 C58 C57 120.7(2) . . ? C60 C59 C58 120.4(2) . . ? C59 C60 C61 119.7(2) . . ? C60 C61 C62 120.3(2) . . ? C61 C62 C57 121.0(2) . . ? C68 C63 C64 118.68(19) . . ? C68 C63 P4 124.30(15) . . ? C64 C63 P4 117.00(17) . . ? C65 C64 C63 120.4(2) . . ? C66 C65 C64 120.3(2) . . ? C65 C66 C67 119.8(2) . . ? C66 C67 C68 120.1(2) . . ? C63 C68 C67 120.7(2) . . ? C74 C69 C70 118.2(2) . . ? C74 C69 C42 120.53(18) . . ? C70 C69 C42 121.2(2) . . ? C69 C70 C71 120.8(2) . . ? C72 C71 C70 120.2(2) . . ? C71 C72 C73 119.5(2) . . ? C74 C73 C72 120.0(2) . . ? C69 C74 C73 121.2(2) . . ? C80 C75 C76 117.2(2) . . ? C80 C75 C41 123.59(18) . . ? C76 C75 C41 119.18(18) . . ? C77 C76 C75 121.4(2) . . ? C78 C77 C76 120.2(2) . . ? C77 C78 C79 119.4(2) . . ? C80 C79 C78 120.7(2) . . ? C79 C80 C75 121.0(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.236 _refine_diff_density_min -0.400 _refine_diff_density_rms 0.046 #============================================