# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Jones, Cameron' 'Junk, Peter' 'Richards, Anne F.' 'Waugh, M.' _publ_contact_author_name 'Dr Cameron Jones' _publ_contact_author_address ; Chemistry Department Cardiff University PO Box 912 Park Place Cardiff CF10 3TB UK ; _publ_contact_author_email 'JONESCA6@CARDIFF.AC.UK' _publ_section_title ; The interaction of phosphavinyl Grignard reagents with group 15 halides: synthesis and structural characterization of novel heterocyclic and heterocage compounds ; data_compound_10 _database_code_CSD 187286 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H38 As Cl P2' _chemical_formula_weight 474.83 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' 'As' 'As' 0.0499 2.0058 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 10.1511(11) _cell_length_b 24.438(3) _cell_length_c 9.8440(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2442.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.291 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 1.637 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.7354 _exptl_absorpt_correction_T_max 0.7913 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 10121 _diffrn_reflns_av_R_equivalents 0.0771 _diffrn_reflns_av_sigmaI/netI 0.0444 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 23.29 _reflns_number_total 1725 _reflns_number_gt 1447 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1005P)^2^+10.6041P] 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 0.011(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1725 _refine_ls_number_parameters 164 _refine_ls_number_restraints 42 _refine_ls_R_factor_all 0.1051 _refine_ls_R_factor_gt 0.0923 _refine_ls_wR_factor_ref 0.2470 _refine_ls_wR_factor_gt 0.2392 _refine_ls_goodness_of_fit_ref 1.220 _refine_ls_restrained_S_all 1.214 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 As1 As 0.06487(16) 0.28305(6) 0.17702(16) 0.0436(6) Uani 0.50 1 d P . . Cl1 Cl 0.0000 0.20231(13) 0.2500 0.0746(11) Uani 1 2 d S . . P1 P 0.0453(4) 0.39044(16) 0.2008(4) 0.0391(10) Uani 0.50 1 d P . . C1 C 0.1649(8) 0.3948(3) 0.0553(8) 0.048(2) Uani 1 1 d . . . C3 C 0.1866(11) 0.4489(5) -0.1612(12) 0.089(3) Uani 1 1 d U . . H3A H 0.1757 0.4195 -0.2278 0.106 Uiso 1 1 calc R A 1 H3B H 0.1528 0.4825 -0.2032 0.106 Uiso 1 1 calc R A 1 C4 C 0.3272(10) 0.4564(4) -0.1391(10) 0.070(3) Uani 1 1 d . C . H4A H 0.3443 0.4945 -0.1139 0.084 Uiso 1 1 calc R B 1 H4B H 0.3745 0.4488 -0.2239 0.084 Uiso 1 1 calc R B 1 C7 C -0.0845(7) 0.3351(3) 0.1731(8) 0.0426(18) Uani 1 1 d . . . C8 C -0.1982(8) 0.3322(3) 0.0714(8) 0.052(2) Uani 1 1 d . C . C9 C -0.2504(9) 0.3882(4) 0.0376(11) 0.071(3) Uani 1 1 d . . . H9A H -0.3130 0.3855 -0.0366 0.107 Uiso 1 1 calc R C . H9B H -0.1780 0.4118 0.0109 0.107 Uiso 1 1 calc R . . H9C H -0.2940 0.4035 0.1167 0.107 Uiso 1 1 calc R . . C10 C -0.3076(9) 0.2971(4) 0.1280(9) 0.068(3) Uani 1 1 d . . . H10A H -0.3796 0.2956 0.0633 0.102 Uiso 1 1 calc R C . H10B H -0.3387 0.3126 0.2127 0.102 Uiso 1 1 calc R . . H10C H -0.2747 0.2604 0.1441 0.102 Uiso 1 1 calc R . . C11 C -0.1473(9) 0.3037(5) -0.0591(9) 0.071(3) Uani 1 1 d . . . H11A H -0.2164 0.3035 -0.1272 0.107 Uiso 1 1 calc R C . H11B H -0.1223 0.2663 -0.0380 0.107 Uiso 1 1 calc R . . H11C H -0.0714 0.3233 -0.0937 0.107 Uiso 1 1 calc R . . P1' P 0.0978(4) 0.32961(16) 0.1325(4) 0.0390(10) Uani 0.50 1 d P . . C2A C 0.102(2) 0.4362(14) -0.045(3) 0.049(8) Uani 0.37(3) 1 d PU C 1 H2A1 H 0.0182 0.4211 -0.0778 0.059 Uiso 0.37(3) 1 calc PR C 1 H2A2 H 0.0819 0.4701 0.0044 0.059 Uiso 0.37(3) 1 calc PR C 1 C5A C 0.377(3) 0.4201(14) -0.032(3) 0.055(8) Uani 0.37(3) 1 d PU C 1 H5A1 H 0.4283 0.3920 -0.0793 0.065 Uiso 0.37(3) 1 calc PR C 1 H5A2 H 0.4413 0.4421 0.0186 0.065 Uiso 0.37(3) 1 calc PR C 1 C6A C 0.308(3) 0.3931(12) 0.063(3) 0.039(7) Uani 0.37(3) 1 d PU C 1 H6A1 H 0.3341 0.4075 0.1522 0.047 Uiso 0.37(3) 1 calc PR C 1 H6A2 H 0.3351 0.3546 0.0604 0.047 Uiso 0.37(3) 1 calc PR C 1 C2B C 0.1178(16) 0.4050(10) -0.0811(18) 0.065(5) Uani 0.63(3) 1 d PU C 2 H2B1 H 0.0242 0.4146 -0.0755 0.078 Uiso 0.63(3) 1 calc PR C 2 H2B2 H 0.1241 0.3708 -0.1324 0.078 Uiso 0.63(3) 1 calc PR C 2 C5B C 0.374(2) 0.4443(11) -0.002(2) 0.081(6) Uani 0.63(3) 1 d PU C 2 H5B1 H 0.4568 0.4243 -0.0121 0.097 Uiso 0.63(3) 1 calc PR C 2 H5B2 H 0.3955 0.4795 0.0399 0.097 Uiso 0.63(3) 1 calc PR C 2 C6B C 0.297(2) 0.4146(11) 0.096(2) 0.064(5) Uani 0.63(3) 1 d PU C 2 H6B1 H 0.2860 0.4381 0.1757 0.077 Uiso 0.63(3) 1 calc PR C 2 H6B2 H 0.3487 0.3828 0.1247 0.077 Uiso 0.63(3) 1 calc PR C 2 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 As1 0.0446(10) 0.0482(10) 0.0380(10) -0.0058(7) 0.0041(7) 0.0052(7) Cl1 0.084(2) 0.0491(17) 0.091(3) 0.000 0.005(2) 0.000 P1 0.036(2) 0.048(2) 0.034(2) -0.0022(17) 0.0005(15) 0.0023(16) C1 0.044(4) 0.056(5) 0.043(5) 0.003(4) 0.001(4) -0.006(4) C3 0.089(6) 0.098(7) 0.080(6) 0.023(6) -0.002(5) -0.027(6) C4 0.071(6) 0.087(7) 0.051(5) 0.014(5) 0.010(5) 0.001(5) C7 0.043(4) 0.046(4) 0.039(4) -0.003(3) 0.000(3) 0.003(3) C8 0.048(5) 0.066(5) 0.042(4) -0.008(4) -0.013(4) -0.005(4) C9 0.047(5) 0.088(7) 0.078(7) 0.009(6) -0.020(5) 0.004(5) C10 0.060(6) 0.105(8) 0.038(5) 0.000(5) -0.004(4) -0.028(5) C11 0.051(5) 0.121(9) 0.043(5) -0.006(5) -0.004(4) 0.002(5) P1' 0.038(2) 0.044(2) 0.035(2) 0.0024(18) 0.0037(16) -0.0003(16) C2A 0.039(10) 0.060(11) 0.049(10) 0.005(8) -0.008(7) -0.003(8) C5A 0.047(10) 0.061(11) 0.056(11) 0.002(9) 0.012(8) 0.007(8) C6A 0.037(9) 0.040(10) 0.042(10) 0.004(8) 0.005(7) 0.004(8) C2B 0.059(8) 0.078(10) 0.057(8) 0.008(7) -0.008(6) -0.007(7) C5B 0.075(9) 0.084(10) 0.084(10) 0.001(8) -0.006(8) -0.009(8) C6B 0.061(8) 0.071(9) 0.059(9) 0.001(7) -0.004(7) -0.009(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 As1 P1' 1.265(4) . ? As1 As1 1.949(3) 4 ? As1 C7 1.959(8) 4 ? As1 C7 1.980(7) . ? As1 Cl1 2.201(3) . ? As1 P1 2.642(4) . ? As1 P1' 2.746(4) 4 ? Cl1 As1 2.201(3) 4 ? P1 P1 1.337(8) 4 ? P1 P1' 1.716(5) . ? P1 C7 1.878(8) 4 ? P1 C1 1.880(9) . ? P1 C7 1.907(8) . ? P1 P1' 2.649(5) 4 ? C1 C2B 1.448(17) . ? C1 C6A 1.46(3) . ? C1 C6B 1.48(2) . ? C1 C2A 1.55(3) . ? C1 P1' 1.893(9) . ? C3 C4 1.456(14) . ? C3 C2A 1.47(3) . ? C3 C2B 1.50(2) . ? C4 C5A 1.47(3) . ? C4 C5B 1.46(2) . ? C7 C8 1.530(11) . ? C7 P1 1.878(8) 4 ? C7 P1' 1.898(8) . ? C7 P1' 1.923(9) 4 ? C7 As1 1.959(8) 4 ? C8 C9 1.505(13) . ? C8 C10 1.510(12) . ? C8 C11 1.551(12) . ? P1' C7 1.923(9) 4 ? P1' P1 2.649(5) 4 ? P1' As1 2.746(4) 4 ? C5A C6A 1.34(4) . ? C5B C6B 1.43(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 P1' As1 As1 115.74(19) . 4 ? P1' As1 C7 69.5(3) . 4 ? As1 As1 C7 60.9(2) 4 4 ? P1' As1 C7 67.5(3) . . ? As1 As1 C7 59.8(2) 4 . ? C7 As1 C7 71.0(4) 4 . ? P1' As1 Cl1 177.7(2) . . ? As1 As1 Cl1 63.71(5) 4 . ? C7 As1 Cl1 111.6(2) 4 . ? C7 As1 Cl1 110.7(2) . . ? P1' As1 P1 32.5(2) . . ? As1 As1 P1 83.34(9) 4 . ? C7 As1 P1 45.2(2) 4 . ? C7 As1 P1 46.0(2) . . ? Cl1 As1 P1 147.06(12) . . ? P1' As1 P1' 91.3(3) . 4 ? As1 As1 P1' 24.51(9) 4 4 ? C7 As1 P1' 43.7(2) 4 4 ? C7 As1 P1' 44.4(2) . 4 ? Cl1 As1 P1' 88.20(10) . 4 ? P1 As1 P1' 58.85(12) . 4 ? As1 Cl1 As1 52.57(11) . 4 ? P1 P1 P1' 119.86(19) 4 . ? P1 P1 C7 70.5(3) 4 4 ? P1' P1 C7 64.5(3) . 4 ? P1 P1 C1 175.4(4) 4 . ? P1' P1 C1 63.3(3) . . ? C7 P1 C1 114.1(4) 4 . ? P1 P1 C7 68.1(3) 4 . ? P1' P1 C7 62.9(3) . . ? C7 P1 C7 74.4(5) 4 . ? C1 P1 C7 112.2(4) . . ? P1 P1 As1 96.65(9) 4 . ? P1' P1 As1 23.33(15) . . ? C7 P1 As1 47.8(2) 4 . ? C1 P1 As1 86.6(3) . . ? C7 P1 As1 48.3(2) . . ? P1 P1 P1' 34.19(12) 4 4 ? P1' P1 P1' 85.8(3) . 4 ? C7 P1 P1' 45.8(3) 4 4 ? C1 P1 P1' 149.1(3) . 4 ? C7 P1 P1' 46.5(3) . 4 ? As1 P1 P1' 62.52(13) . 4 ? C2B C1 C6A 112.6(13) . . ? C2B C1 C6B 119.6(11) . . ? C6A C1 C6B 24.6(10) . . ? C2B C1 C2A 33.1(10) . . ? C6A C1 C2A 117.8(14) . . ? C6B C1 C2A 109.5(12) . . ? C2B C1 P1 120.2(9) . . ? C6A C1 P1 127.0(12) . . ? C6B C1 P1 113.5(10) . . ? C2A C1 P1 104.6(11) . . ? C2B C1 P1' 113.5(10) . . ? C6A C1 P1' 108.2(11) . . ? C6B C1 P1' 119.5(10) . . ? C2A C1 P1' 130.9(11) . . ? P1 C1 P1' 54.1(3) . . ? C4 C3 C2A 119.0(12) . . ? C4 C3 C2B 117.8(11) . . ? C2A C3 C2B 33.5(10) . . ? C3 C4 C5A 111.8(14) . . ? C3 C4 C5B 115.4(11) . . ? C5A C4 C5B 26.1(12) . . ? C8 C7 P1 128.8(6) . 4 ? C8 C7 P1' 126.5(6) . . ? P1 C7 P1' 89.1(4) 4 . ? C8 C7 P1 130.4(6) . . ? P1 C7 P1 41.4(3) 4 . ? P1' C7 P1 53.6(3) . . ? C8 C7 P1' 126.5(6) . 4 ? P1 C7 P1' 53.7(3) 4 4 ? P1' C7 P1' 105.9(4) . 4 ? P1 C7 P1' 87.5(4) . 4 ? C8 C7 As1 122.6(6) . 4 ? P1 C7 As1 87.0(3) 4 4 ? P1' C7 As1 90.8(3) . 4 ? P1 C7 As1 106.4(4) . 4 ? P1' C7 As1 38.0(2) 4 4 ? C8 C7 As1 124.1(5) . . ? P1 C7 As1 106.7(4) 4 . ? P1' C7 As1 37.98(19) . . ? P1 C7 As1 85.6(3) . . ? P1' C7 As1 89.4(3) 4 . ? As1 C7 As1 59.3(2) 4 . ? C9 C8 C10 109.9(8) . . ? C9 C8 C7 111.6(7) . . ? C10 C8 C7 109.9(7) . . ? C9 C8 C11 110.1(8) . . ? C10 C8 C11 107.1(7) . . ? C7 C8 C11 108.1(7) . . ? As1 P1' P1 124.2(3) . . ? As1 P1' C1 172.9(4) . . ? P1 P1' C1 62.6(3) . . ? As1 P1' C7 74.5(3) . . ? P1 P1' C7 63.4(3) . . ? C1 P1' C7 112.1(4) . . ? As1 P1' C7 72.5(3) . 4 ? P1 P1' C7 61.8(3) . 4 ? C1 P1' C7 111.5(4) . 4 ? C7 P1' C7 73.5(4) . 4 ? As1 P1' P1 98.3(2) . 4 ? P1 P1' P1 25.95(17) . 4 ? C1 P1' P1 88.5(3) . 4 ? C7 P1' P1 45.1(3) . 4 ? C7 P1' P1 46.0(3) 4 4 ? As1 P1' As1 39.75(15) . 4 ? P1 P1' As1 84.5(2) . 4 ? C1 P1' As1 147.1(3) . 4 ? C7 P1' As1 45.5(2) . 4 ? C7 P1' As1 46.1(2) 4 4 ? P1 P1' As1 58.62(12) 4 4 ? C3 C2A C1 113.0(18) . . ? C6A C5A C4 128(2) . . ? C5A C6A C1 118(2) . . ? C1 C2B C3 117.1(13) . . ? C6B C5B C4 123.3(17) . . ? C5B C6B C1 118.4(16) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 23.29 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.459 _refine_diff_density_min -0.536 _refine_diff_density_rms 0.109 data_compound_12 _database_code_CSD 187287 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H40 O5 P2 W' _chemical_formula_weight 690.38 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' 'W' 'W' -0.8490 6.8722 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.441(2) _cell_length_b 18.702(4) _cell_length_c 15.226(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.99(3) _cell_angle_gamma 90.00 _cell_volume 2885.0(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.589 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 4.148 _exptl_absorpt_correction_type Diffabs _exptl_absorpt_correction_T_min 0.55 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 CAD4' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5653 _diffrn_reflns_av_R_equivalents 0.0478 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.20 _reflns_number_total 5199 _reflns_number_gt 4740 _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^)+(0.0998P)^2^+8.3125P] 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 5199 _refine_ls_number_parameters 322 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1366 _refine_ls_wR_factor_gt 0.1305 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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 W1 W 0.242062(19) 0.124785(11) 0.342036(13) 0.01621(13) Uani 1 1 d . . . P1 P 0.22516(12) 0.18188(7) 0.49340(9) 0.0141(3) Uani 1 1 d . . . P2 P 0.32493(13) 0.27993(7) 0.55561(9) 0.0161(3) Uani 1 1 d . . . O1 O 0.5513(4) 0.1557(3) 0.3936(3) 0.0374(11) Uani 1 1 d . . . O2 O 0.1618(5) 0.2573(3) 0.2085(3) 0.0393(11) Uani 1 1 d . . . O3 O -0.0573(5) 0.0755(3) 0.2786(3) 0.0445(13) Uani 1 1 d . . . O4 O 0.2927(5) -0.0261(2) 0.4396(3) 0.0390(11) Uani 1 1 d . . . O5 O 0.2858(5) 0.0507(3) 0.1667(3) 0.0312(10) Uani 1 1 d . . . C1 C 0.0862(5) 0.2353(3) 0.5136(3) 0.0163(10) Uani 1 1 d . . . C2 C 0.1472(5) 0.2988(3) 0.5414(3) 0.0163(10) Uani 1 1 d . . . C3 C -0.0550(5) 0.2060(3) 0.4951(4) 0.0200(11) Uani 1 1 d . . . C4 C -0.0524(7) 0.1235(3) 0.4959(5) 0.0273(15) Uani 1 1 d . . . H4A H 0.0030 0.1067 0.4583 0.041 Uiso 1 1 calc R . . H4B H -0.1404 0.1055 0.4733 0.041 Uiso 1 1 calc R . . H4C H -0.0183 0.1069 0.5567 0.041 Uiso 1 1 calc R . . C5 C -0.1334(6) 0.2264(4) 0.5644(4) 0.0308(14) Uani 1 1 d . . . H5A H -0.2188 0.2043 0.5482 0.046 Uiso 1 1 calc R . . H5B H -0.1435 0.2774 0.5650 0.046 Uiso 1 1 calc R . . H5C H -0.0869 0.2104 0.6234 0.046 Uiso 1 1 calc R . . C6 C -0.1275(6) 0.2316(4) 0.3993(4) 0.0289(13) Uani 1 1 d . . . H6A H -0.0788 0.2168 0.3564 0.043 Uiso 1 1 calc R . . H6B H -0.1342 0.2828 0.3989 0.043 Uiso 1 1 calc R . . H6C H -0.2143 0.2112 0.3832 0.043 Uiso 1 1 calc R . . C7 C 0.1025(6) 0.3679(3) 0.5785(4) 0.0200(12) Uani 1 1 d . . . C8 C 0.2077(6) 0.4258(3) 0.5833(4) 0.0262(12) Uani 1 1 d . . . H8A H 0.1824 0.4681 0.6106 0.039 Uiso 1 1 calc R . . H8B H 0.2158 0.4368 0.5232 0.039 Uiso 1 1 calc R . . H8C H 0.2909 0.4089 0.6189 0.039 Uiso 1 1 calc R . . C9 C -0.0269(6) 0.3978(4) 0.5192(4) 0.0266(13) Uani 1 1 d . . . H9A H -0.0442 0.4439 0.5416 0.040 Uiso 1 1 calc R . . H9B H -0.0982 0.3660 0.5211 0.040 Uiso 1 1 calc R . . H9C H -0.0190 0.4023 0.4579 0.040 Uiso 1 1 calc R . . C10 C 0.0919(7) 0.3544(4) 0.6762(4) 0.0269(13) Uani 1 1 d . . . H10A H 0.0637 0.3974 0.7003 0.040 Uiso 1 1 calc R . . H10B H 0.1766 0.3404 0.7126 0.040 Uiso 1 1 calc R . . H10C H 0.0290 0.3171 0.6765 0.040 Uiso 1 1 calc R . . C11 C 0.2763(6) 0.1175(3) 0.5889(4) 0.0193(12) Uani 1 1 d . . . H11 H 0.2295 0.0724 0.5709 0.023 Uiso 1 1 calc R . . C12 C 0.2457(6) 0.1420(3) 0.6777(4) 0.0197(11) Uani 1 1 d . . . H12A H 0.2895 0.1873 0.6960 0.024 Uiso 1 1 calc R . . H12B H 0.1513 0.1496 0.6680 0.024 Uiso 1 1 calc R . . C13 C 0.2911(5) 0.0871(3) 0.7535(4) 0.0211(11) Uani 1 1 d . . . H13A H 0.2734 0.1050 0.8092 0.025 Uiso 1 1 calc R . . H13B H 0.2424 0.0429 0.7377 0.025 Uiso 1 1 calc R . . C14 C 0.4384(6) 0.0729(3) 0.7675(4) 0.0252(12) Uani 1 1 d . . . H14A H 0.4651 0.0361 0.8132 0.030 Uiso 1 1 calc R . . H14B H 0.4871 0.1161 0.7894 0.030 Uiso 1 1 calc R . . C15 C 0.4727(6) 0.0489(3) 0.6797(4) 0.0256(12) Uani 1 1 d . . . H15A H 0.5676 0.0435 0.6901 0.031 Uiso 1 1 calc R . . H15B H 0.4324 0.0028 0.6615 0.031 Uiso 1 1 calc R . . C16 C 0.4241(5) 0.1031(3) 0.6044(4) 0.0198(11) Uani 1 1 d . . . H16A H 0.4423 0.0853 0.5488 0.024 Uiso 1 1 calc R . . H16B H 0.4721 0.1475 0.6199 0.024 Uiso 1 1 calc R . . C17 C 0.3923(5) 0.3219(3) 0.4651(4) 0.0196(11) Uani 1 1 d . . . H17 H 0.4319 0.2826 0.4381 0.024 Uiso 1 1 calc R . . C18 C 0.5077(6) 0.3727(3) 0.5066(5) 0.0260(14) Uani 1 1 d . . . H18A H 0.4743 0.4147 0.5311 0.031 Uiso 1 1 calc R . . H18B H 0.5695 0.3488 0.5557 0.031 Uiso 1 1 calc R . . C19 C 0.5785(7) 0.3952(4) 0.4330(5) 0.0377(16) Uani 1 1 d . . . H19A H 0.6484 0.4287 0.4585 0.045 Uiso 1 1 calc R . . H19B H 0.6184 0.3534 0.4127 0.045 Uiso 1 1 calc R . . C20 C 0.4837(6) 0.4293(3) 0.3531(5) 0.0333(14) Uani 1 1 d . . . H20A H 0.5302 0.4409 0.3070 0.040 Uiso 1 1 calc R . . H20B H 0.4500 0.4735 0.3723 0.040 Uiso 1 1 calc R . . C21 C 0.3687(7) 0.3794(3) 0.3133(5) 0.0288(15) Uani 1 1 d . . . H21A H 0.4015 0.3367 0.2899 0.035 Uiso 1 1 calc R . . H21B H 0.3079 0.4030 0.2635 0.035 Uiso 1 1 calc R . . C22 C 0.2965(6) 0.3587(3) 0.3857(4) 0.0230(12) Uani 1 1 d . . . H22A H 0.2241 0.3267 0.3600 0.028 Uiso 1 1 calc R . . H22B H 0.2601 0.4012 0.4071 0.028 Uiso 1 1 calc R . . C23 C 0.4386(6) 0.1470(4) 0.3766(4) 0.0236(12) Uani 1 1 d . . . C24 C 0.1927(6) 0.2130(3) 0.2617(4) 0.0258(12) Uani 1 1 d . . . C25 C 0.0484(6) 0.0951(4) 0.3024(4) 0.0269(13) Uani 1 1 d . . . C26 C 0.2775(6) 0.0290(3) 0.4072(4) 0.0235(12) Uani 1 1 d . . . C27 C 0.2691(5) 0.0785(3) 0.2310(4) 0.0227(12) 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 W1 0.01554(18) 0.01884(19) 0.01372(18) -0.00165(7) 0.00253(11) -0.00068(7) P1 0.0130(6) 0.0163(6) 0.0128(6) 0.0001(5) 0.0026(5) 0.0007(5) P2 0.0135(6) 0.0177(6) 0.0156(6) 0.0007(5) 0.0004(5) -0.0001(5) O1 0.018(2) 0.052(3) 0.040(3) -0.006(2) 0.0048(19) -0.004(2) O2 0.049(3) 0.034(3) 0.028(2) 0.004(2) -0.004(2) 0.003(2) O3 0.027(3) 0.060(3) 0.045(3) -0.023(3) 0.005(2) -0.013(2) O4 0.053(3) 0.029(3) 0.040(3) 0.008(2) 0.022(2) 0.004(2) O5 0.034(2) 0.039(3) 0.022(2) -0.0087(18) 0.0097(17) 0.000(2) C1 0.014(2) 0.023(3) 0.012(2) 0.001(2) 0.0034(19) 0.004(2) C2 0.019(3) 0.020(3) 0.009(2) 0.000(2) 0.0035(19) 0.004(2) C3 0.016(3) 0.026(3) 0.019(3) 0.003(2) 0.006(2) -0.002(2) C4 0.021(3) 0.031(4) 0.030(4) 0.001(2) 0.007(3) -0.007(2) C5 0.026(3) 0.038(4) 0.034(3) -0.001(3) 0.017(3) -0.005(3) C6 0.017(3) 0.042(4) 0.024(3) 0.001(3) -0.004(2) 0.000(3) C7 0.023(3) 0.020(3) 0.017(3) -0.001(2) 0.005(2) 0.003(2) C8 0.031(3) 0.020(3) 0.027(3) -0.007(2) 0.007(2) 0.002(2) C9 0.033(3) 0.028(3) 0.018(3) 0.001(3) 0.004(3) 0.008(3) C10 0.032(3) 0.032(3) 0.017(3) -0.001(3) 0.007(2) 0.006(3) C11 0.024(3) 0.019(3) 0.015(3) -0.002(2) 0.005(2) 0.001(2) C12 0.022(3) 0.020(3) 0.017(3) 0.002(2) 0.006(2) 0.001(2) C13 0.031(3) 0.019(3) 0.015(2) 0.003(2) 0.008(2) -0.001(2) C14 0.028(3) 0.030(3) 0.016(3) 0.005(2) 0.002(2) 0.007(2) C15 0.031(3) 0.026(3) 0.020(3) 0.008(2) 0.008(2) 0.010(2) C16 0.020(3) 0.028(3) 0.012(3) 0.004(2) 0.004(2) 0.004(2) C17 0.019(3) 0.019(3) 0.021(3) 0.002(2) 0.005(2) 0.000(2) C18 0.015(3) 0.030(3) 0.029(4) 0.004(2) -0.003(3) -0.008(2) C19 0.022(3) 0.041(4) 0.050(5) 0.016(4) 0.009(3) -0.005(3) C20 0.035(3) 0.025(3) 0.045(4) 0.011(3) 0.020(3) -0.003(3) C21 0.035(4) 0.030(3) 0.024(3) 0.006(2) 0.013(3) 0.001(2) C22 0.016(3) 0.029(3) 0.023(3) 0.002(2) 0.003(2) -0.003(2) C23 0.028(3) 0.025(3) 0.018(3) 0.001(2) 0.008(2) -0.001(3) C24 0.029(3) 0.026(3) 0.019(3) -0.001(2) 0.000(2) -0.001(2) C25 0.025(3) 0.029(3) 0.025(3) -0.011(3) 0.005(2) -0.001(3) C26 0.028(3) 0.025(3) 0.019(3) 0.001(2) 0.010(2) 0.002(2) C27 0.018(3) 0.025(3) 0.024(3) -0.002(2) 0.004(2) 0.003(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 W1 C27 1.979(5) . ? W1 C23 2.034(6) . ? W1 C26 2.037(6) . ? W1 C25 2.042(6) . ? W1 C24 2.044(6) . ? W1 P1 2.5845(14) . ? P1 C1 1.847(5) . ? P1 C11 1.865(6) . ? P1 P2 2.2063(19) . ? P2 C2 1.849(5) . ? P2 C17 1.865(6) . ? O1 C23 1.153(8) . ? O2 C24 1.150(8) . ? O3 C25 1.136(8) . ? O4 C26 1.137(7) . ? O5 C27 1.158(7) . ? C1 C2 1.366(8) . ? C1 C3 1.533(7) . ? C2 C7 1.527(7) . ? C3 C5 1.531(8) . ? C3 C4 1.544(8) . ? C3 C6 1.548(8) . ? C7 C8 1.533(8) . ? C7 C9 1.537(8) . ? C7 C10 1.538(8) . ? C11 C16 1.527(8) . ? C11 C12 1.533(8) . ? C12 C13 1.532(8) . ? C13 C14 1.524(8) . ? C14 C15 1.533(8) . ? C15 C16 1.523(7) . ? C17 C22 1.534(8) . ? C17 C18 1.545(8) . ? C18 C19 1.543(10) . ? C19 C20 1.511(10) . ? C20 C21 1.526(9) . ? C21 C22 1.528(9) . ? 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 C27 W1 C23 88.1(2) . . ? C27 W1 C26 89.1(2) . . ? C23 W1 C26 90.0(2) . . ? C27 W1 C25 88.0(2) . . ? C23 W1 C25 175.4(2) . . ? C26 W1 C25 87.5(3) . . ? C27 W1 C24 84.8(2) . . ? C23 W1 C24 94.7(2) . . ? C26 W1 C24 172.2(2) . . ? C25 W1 C24 87.4(3) . . ? C27 W1 P1 175.50(16) . . ? C23 W1 P1 88.12(17) . . ? C26 W1 P1 88.42(16) . . ? C25 W1 P1 95.71(17) . . ? C24 W1 P1 97.95(17) . . ? C1 P1 C11 107.9(2) . . ? C1 P1 P2 77.75(18) . . ? C11 P1 P2 100.71(19) . . ? C1 P1 W1 126.68(17) . . ? C11 P1 W1 111.10(18) . . ? P2 P1 W1 126.82(7) . . ? C2 P2 C17 112.4(2) . . ? C2 P2 P1 75.64(18) . . ? C17 P2 P1 104.82(18) . . ? C2 C1 C3 136.3(5) . . ? C2 C1 P1 101.3(4) . . ? C3 C1 P1 122.4(4) . . ? C1 C2 C7 133.5(5) . . ? C1 C2 P2 104.5(4) . . ? C7 C2 P2 120.4(4) . . ? C5 C3 C1 115.8(5) . . ? C5 C3 C4 104.8(5) . . ? C1 C3 C4 109.9(5) . . ? C5 C3 C6 110.6(5) . . ? C1 C3 C6 107.0(4) . . ? C4 C3 C6 108.7(5) . . ? C2 C7 C8 109.6(5) . . ? C2 C7 C9 113.3(5) . . ? C8 C7 C9 106.7(5) . . ? C2 C7 C10 108.6(5) . . ? C8 C7 C10 106.7(5) . . ? C9 C7 C10 111.7(5) . . ? C16 C11 C12 109.6(5) . . ? C16 C11 P1 108.8(4) . . ? C12 C11 P1 114.4(4) . . ? C13 C12 C11 111.7(5) . . ? C14 C13 C12 109.9(5) . . ? C13 C14 C15 111.7(5) . . ? C16 C15 C14 110.8(5) . . ? C15 C16 C11 112.0(5) . . ? C22 C17 C18 110.0(5) . . ? C22 C17 P2 118.7(4) . . ? C18 C17 P2 110.6(4) . . ? C19 C18 C17 109.5(6) . . ? C20 C19 C18 111.4(5) . . ? C19 C20 C21 111.1(5) . . ? C20 C21 C22 110.2(6) . . ? C21 C22 C17 109.9(5) . . ? O1 C23 W1 175.8(6) . . ? O2 C24 W1 172.3(5) . . ? O3 C25 W1 176.4(6) . . ? O4 C26 W1 176.2(5) . . ? O5 C27 W1 179.1(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C27 W1 P1 C1 177(2) . . . . ? C23 W1 P1 C1 144.2(3) . . . . ? C26 W1 P1 C1 -125.7(3) . . . . ? C25 W1 P1 C1 -38.4(3) . . . . ? C24 W1 P1 C1 49.7(3) . . . . ? C27 W1 P1 C11 -49(2) . . . . ? C23 W1 P1 C11 -81.4(3) . . . . ? C26 W1 P1 C11 8.6(3) . . . . ? C25 W1 P1 C11 95.9(3) . . . . ? C24 W1 P1 C11 -176.0(3) . . . . ? C27 W1 P1 P2 74(2) . . . . ? C23 W1 P1 P2 41.1(2) . . . . ? C26 W1 P1 P2 131.15(18) . . . . ? C25 W1 P1 P2 -141.6(2) . . . . ? C24 W1 P1 P2 -53.43(19) . . . . ? C1 P1 P2 C2 -5.4(2) . . . . ? C11 P1 P2 C2 -111.6(3) . . . . ? W1 P1 P2 C2 121.58(18) . . . . ? C1 P1 P2 C17 -115.2(2) . . . . ? C11 P1 P2 C17 138.6(3) . . . . ? W1 P1 P2 C17 11.8(2) . . . . ? C11 P1 C1 C2 104.6(4) . . . . ? P2 P1 C1 C2 7.2(3) . . . . ? W1 P1 C1 C2 -119.9(3) . . . . ? C11 P1 C1 C3 -77.7(5) . . . . ? P2 P1 C1 C3 -175.2(4) . . . . ? W1 P1 C1 C3 57.8(5) . . . . ? C3 C1 C2 C7 9.2(10) . . . . ? P1 C1 C2 C7 -173.7(5) . . . . ? C3 C1 C2 P2 174.2(5) . . . . ? P1 C1 C2 P2 -8.7(4) . . . . ? C17 P2 C2 C1 107.7(4) . . . . ? P1 P2 C2 C1 7.3(3) . . . . ? C17 P2 C2 C7 -84.8(5) . . . . ? P1 P2 C2 C7 174.8(4) . . . . ? C2 C1 C3 C5 -42.6(9) . . . . ? P1 C1 C3 C5 140.7(4) . . . . ? C2 C1 C3 C4 -161.1(6) . . . . ? P1 C1 C3 C4 22.3(6) . . . . ? C2 C1 C3 C6 81.1(7) . . . . ? P1 C1 C3 C6 -95.6(5) . . . . ? C1 C2 C7 C8 -170.5(6) . . . . ? P2 C2 C7 C8 26.3(6) . . . . ? C1 C2 C7 C9 -51.5(8) . . . . ? P2 C2 C7 C9 145.4(4) . . . . ? C1 C2 C7 C10 73.2(8) . . . . ? P2 C2 C7 C10 -89.9(5) . . . . ? C1 P1 C11 C16 -149.4(4) . . . . ? P2 P1 C11 C16 -68.9(4) . . . . ? W1 P1 C11 C16 67.7(4) . . . . ? C1 P1 C11 C12 -26.5(5) . . . . ? P2 P1 C11 C12 53.9(4) . . . . ? W1 P1 C11 C12 -169.4(4) . . . . ? C16 C11 C12 C13 -57.1(6) . . . . ? P1 C11 C12 C13 -179.5(4) . . . . ? C11 C12 C13 C14 57.1(6) . . . . ? C12 C13 C14 C15 -55.8(7) . . . . ? C13 C14 C15 C16 55.3(7) . . . . ? C14 C15 C16 C11 -55.5(7) . . . . ? C12 C11 C16 C15 56.1(6) . . . . ? P1 C11 C16 C15 -178.2(4) . . . . ? C2 P2 C17 C22 -6.6(5) . . . . ? P1 P2 C17 C22 73.7(4) . . . . ? C2 P2 C17 C18 121.9(4) . . . . ? P1 P2 C17 C18 -157.8(4) . . . . ? C22 C17 C18 C19 -57.7(7) . . . . ? P2 C17 C18 C19 169.2(4) . . . . ? C17 C18 C19 C20 56.5(8) . . . . ? C18 C19 C20 C21 -56.6(8) . . . . ? C19 C20 C21 C22 57.4(7) . . . . ? C20 C21 C22 C17 -58.8(7) . . . . ? C18 C17 C22 C21 59.5(6) . . . . ? P2 C17 C22 C21 -171.7(4) . . . . ? C27 W1 C23 O1 -33(8) . . . . ? C26 W1 C23 O1 56(8) . . . . ? C25 W1 C23 O1 -1(10) . . . . ? C24 W1 C23 O1 -118(8) . . . . ? P1 W1 C23 O1 145(8) . . . . ? C27 W1 C24 O2 23(4) . . . . ? C23 W1 C24 O2 110(4) . . . . ? C26 W1 C24 O2 -17(5) . . . . ? C25 W1 C24 O2 -65(4) . . . . ? P1 W1 C24 O2 -161(4) . . . . ? C27 W1 C25 O3 35(10) . . . . ? C23 W1 C25 O3 3(12) . . . . ? C26 W1 C25 O3 -55(10) . . . . ? C24 W1 C25 O3 120(10) . . . . ? P1 W1 C25 O3 -143(10) . . . . ? C27 W1 C26 O4 -47(8) . . . . ? C23 W1 C26 O4 -136(8) . . . . ? C25 W1 C26 O4 41(8) . . . . ? C24 W1 C26 O4 -8(9) . . . . ? P1 W1 C26 O4 136(8) . . . . ? C23 W1 C27 O5 71(36) . . . . ? C26 W1 C27 O5 -19(36) . . . . ? C25 W1 C27 O5 -107(36) . . . . ? C24 W1 C27 O5 166(36) . . . . ? P1 W1 C27 O5 38(37) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.657 (near W(1)) _refine_diff_density_min -3.560 _refine_diff_density_rms 0.257 data_compound_13 _database_code_CSD 187288 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H40 Cl2 P4' _chemical_formula_weight 499.32 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 monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.4270(19) _cell_length_b 16.555(3) _cell_length_c 16.512(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.34(3) _cell_angle_gamma 90.00 _cell_volume 2572.6(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 0.509 _exptl_absorpt_correction_type 'Sortav (blessing)' _exptl_absorpt_correction_T_min 0.93 _exptl_absorpt_correction_T_max 0.96 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 48132 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.91 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5884 _reflns_number_gt 5321 _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^)+(0.0266P)^2^+1.3727P] 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 5884 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_ref 0.0700 _refine_ls_wR_factor_gt 0.0678 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 Cl1 Cl 0.05922(4) 0.22853(2) 0.30755(2) 0.03165(9) Uani 1 1 d . . . Cl2 Cl 0.40477(4) 0.23985(2) 0.26440(2) 0.03351(10) Uani 1 1 d . . . P1 P 0.01321(4) 0.32325(2) 0.22706(2) 0.02193(8) Uani 1 1 d . . . P2 P 0.30941(4) 0.28961(2) 0.15807(2) 0.02094(8) Uani 1 1 d . . . P3 P 0.06519(3) 0.38236(2) 0.09219(2) 0.01799(8) Uani 1 1 d . . . P4 P 0.14242(4) 0.19774(2) 0.12510(2) 0.02099(8) Uani 1 1 d . . . C1 C 0.18197(14) 0.36592(8) 0.19156(8) 0.0191(3) Uani 1 1 d . . . C2 C -0.00178(14) 0.27794(8) 0.12202(8) 0.0195(3) Uani 1 1 d . . . C3 C 0.24368(15) 0.43945(9) 0.24227(8) 0.0229(3) Uani 1 1 d . . . C4 C 0.24296(17) 0.41884(10) 0.33282(9) 0.0309(3) Uani 1 1 d . . . H4A H 0.2833 0.4629 0.3642 0.046 Uiso 1 1 calc R . . H4B H 0.2981 0.3709 0.3437 0.046 Uiso 1 1 calc R . . H4C H 0.1470 0.4099 0.3472 0.046 Uiso 1 1 calc R . . C5 C 0.15283(18) 0.51477(10) 0.22642(11) 0.0365(4) Uani 1 1 d . . . H5A H 0.0558 0.5029 0.2367 0.055 Uiso 1 1 calc R . . H5B H 0.1585 0.5312 0.1709 0.055 Uiso 1 1 calc R . . H5C H 0.1870 0.5575 0.2616 0.055 Uiso 1 1 calc R . . C6 C 0.39715(16) 0.45967(10) 0.22391(9) 0.0320(3) Uani 1 1 d . . . H6A H 0.4013 0.4725 0.1674 0.048 Uiso 1 1 calc R . . H6B H 0.4570 0.4140 0.2368 0.048 Uiso 1 1 calc R . . H6C H 0.4293 0.5052 0.2560 0.048 Uiso 1 1 calc R . . C7 C 0.18315(14) 0.37887(8) 0.00440(8) 0.0194(3) Uani 1 1 d . . . H7 H 0.2524 0.3350 0.0124 0.023 Uiso 1 1 calc R . . C8 C 0.26102(16) 0.46036(9) 0.00190(8) 0.0261(3) Uani 1 1 d . . . H8A H 0.1920 0.5038 -0.0034 0.031 Uiso 1 1 calc R . . H8B H 0.3174 0.4682 0.0523 0.031 Uiso 1 1 calc R . . C9 C 0.35777(16) 0.46341(10) -0.06920(9) 0.0299(3) Uani 1 1 d . . . H9A H 0.4037 0.5158 -0.0704 0.036 Uiso 1 1 calc R . . H9B H 0.4312 0.4226 -0.0617 0.036 Uiso 1 1 calc R . . C10 C 0.27414(16) 0.44893(10) -0.14960(9) 0.0298(3) Uani 1 1 d . . . H10A H 0.2084 0.4932 -0.1604 0.036 Uiso 1 1 calc R . . H10B H 0.3390 0.4472 -0.1931 0.036 Uiso 1 1 calc R . . C11 C 0.19227(16) 0.37005(10) -0.14762(9) 0.0280(3) Uani 1 1 d . . . H11A H 0.2589 0.3254 -0.1436 0.034 Uiso 1 1 calc R . . H11B H 0.1347 0.3640 -0.1979 0.034 Uiso 1 1 calc R . . C12 C 0.09618(14) 0.36676(9) -0.07602(8) 0.0226(3) Uani 1 1 d . . . H12A H 0.0484 0.3149 -0.0755 0.027 Uiso 1 1 calc R . . H12B H 0.0243 0.4086 -0.0822 0.027 Uiso 1 1 calc R . . C13 C -0.15747(14) 0.25234(9) 0.09387(9) 0.0238(3) Uani 1 1 d . . . C14 C -0.26674(16) 0.31049(11) 0.12743(12) 0.0385(4) Uani 1 1 d . . . H14A H -0.2425 0.3650 0.1142 0.058 Uiso 1 1 calc R . . H14B H -0.2664 0.3047 0.1853 0.058 Uiso 1 1 calc R . . H14C H -0.3596 0.2980 0.1038 0.058 Uiso 1 1 calc R . . C15 C -0.18860(17) 0.16765(10) 0.12561(11) 0.0358(4) Uani 1 1 d . . . H15A H -0.1681 0.1660 0.1832 0.054 Uiso 1 1 calc R . . H15B H -0.1303 0.1289 0.0998 0.054 Uiso 1 1 calc R . . H15C H -0.2869 0.1549 0.1137 0.054 Uiso 1 1 calc R . . C16 C -0.17926(16) 0.25408(10) 0.00147(10) 0.0321(3) Uani 1 1 d . . . H16A H -0.2721 0.2337 -0.0144 0.048 Uiso 1 1 calc R . . H16B H -0.1086 0.2210 -0.0218 0.048 Uiso 1 1 calc R . . H16C H -0.1707 0.3086 -0.0174 0.048 Uiso 1 1 calc R . . C17 C 0.19415(16) 0.16938(8) 0.02063(8) 0.0243(3) Uani 1 1 d . . . H17 H 0.1814 0.2155 -0.0163 0.029 Uiso 1 1 calc R . . C18 C 0.10569(17) 0.09707(10) -0.01151(10) 0.0315(3) Uani 1 1 d . . . H18A H 0.1135 0.0534 0.0277 0.038 Uiso 1 1 calc R . . H18B H 0.0065 0.1127 -0.0182 0.038 Uiso 1 1 calc R . . C19 C 0.1561(2) 0.06764(11) -0.09276(10) 0.0419(4) Uani 1 1 d . . . H19A H 0.0993 0.0216 -0.1112 0.050 Uiso 1 1 calc R . . H19B H 0.1428 0.1102 -0.1328 0.050 Uiso 1 1 calc R . . C20 C 0.3118(2) 0.04351(11) -0.08520(12) 0.0465(5) Uani 1 1 d . . . H20A H 0.3234 -0.0031 -0.0499 0.056 Uiso 1 1 calc R . . H20B H 0.3427 0.0285 -0.1382 0.056 Uiso 1 1 calc R . . C21 C 0.4034(2) 0.11237(13) -0.05106(13) 0.0518(5) Uani 1 1 d . . . H21A H 0.4026 0.1560 -0.0903 0.062 Uiso 1 1 calc R . . H21B H 0.5006 0.0938 -0.0422 0.062 Uiso 1 1 calc R . . C22 C 0.35112(17) 0.14414(11) 0.02853(11) 0.0371(4) Uani 1 1 d . . . H22A H 0.4084 0.1903 0.0461 0.044 Uiso 1 1 calc R . . H22B H 0.3634 0.1025 0.0697 0.044 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 0.0396(2) 0.0336(2) 0.02207(17) 0.00554(14) 0.00445(14) -0.00560(16) Cl2 0.0338(2) 0.0357(2) 0.02947(19) 0.00504(15) -0.01168(15) 0.00640(16) P1 0.02116(17) 0.02593(18) 0.01896(17) -0.00081(14) 0.00354(13) -0.00303(14) P2 0.01822(16) 0.02517(18) 0.01912(17) 0.00050(13) -0.00173(13) 0.00187(13) P3 0.01626(15) 0.01981(17) 0.01765(16) 0.00073(12) -0.00105(12) -0.00099(12) P4 0.02204(17) 0.02071(17) 0.02020(17) 0.00101(13) 0.00100(13) 0.00074(13) C1 0.0192(6) 0.0226(6) 0.0155(6) 0.0013(5) -0.0003(5) -0.0012(5) C2 0.0188(6) 0.0197(6) 0.0200(6) -0.0001(5) 0.0015(5) -0.0015(5) C3 0.0240(7) 0.0252(7) 0.0191(6) -0.0017(5) -0.0024(5) -0.0044(5) C4 0.0362(8) 0.0376(9) 0.0190(7) -0.0046(6) 0.0015(6) -0.0090(7) C5 0.0410(9) 0.0252(8) 0.0416(9) -0.0093(7) -0.0120(7) 0.0008(7) C6 0.0296(8) 0.0440(9) 0.0219(7) -0.0022(6) -0.0028(6) -0.0141(7) C7 0.0188(6) 0.0223(6) 0.0168(6) 0.0020(5) -0.0006(5) -0.0003(5) C8 0.0275(7) 0.0310(8) 0.0195(7) -0.0005(6) -0.0009(5) -0.0105(6) C9 0.0249(7) 0.0404(9) 0.0242(7) 0.0015(6) 0.0009(6) -0.0126(6) C10 0.0306(8) 0.0394(9) 0.0196(7) 0.0011(6) 0.0028(6) -0.0118(7) C11 0.0297(7) 0.0349(8) 0.0196(7) -0.0037(6) 0.0019(6) -0.0074(6) C12 0.0224(6) 0.0269(7) 0.0182(6) 0.0009(5) -0.0014(5) -0.0064(5) C13 0.0170(6) 0.0253(7) 0.0289(7) -0.0030(6) 0.0009(5) -0.0048(5) C14 0.0185(7) 0.0415(9) 0.0556(11) -0.0134(8) 0.0036(7) -0.0035(7) C15 0.0311(8) 0.0337(9) 0.0423(9) 0.0040(7) -0.0006(7) -0.0132(7) C16 0.0230(7) 0.0414(9) 0.0310(8) -0.0001(7) -0.0061(6) -0.0066(6) C17 0.0319(7) 0.0202(7) 0.0209(7) -0.0001(5) 0.0022(5) 0.0019(6) C18 0.0321(8) 0.0283(8) 0.0335(8) -0.0073(6) -0.0043(6) 0.0024(6) C19 0.0602(11) 0.0337(9) 0.0308(9) -0.0101(7) -0.0057(8) 0.0040(8) C20 0.0595(12) 0.0392(10) 0.0425(10) -0.0162(8) 0.0167(9) 0.0014(9) C21 0.0503(11) 0.0498(11) 0.0585(12) -0.0198(10) 0.0302(10) -0.0085(9) C22 0.0281(8) 0.0411(9) 0.0429(9) -0.0155(8) 0.0103(7) -0.0031(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 P1 2.0848(6) . ? Cl2 P2 2.0943(7) . ? P1 C1 1.8660(14) . ? P1 C2 1.8873(14) . ? P2 C1 1.8500(14) . ? P2 P4 2.2334(6) . ? P3 C7 1.8786(14) . ? P3 C2 1.9146(14) . ? P3 C1 1.9411(14) . ? P4 C17 1.8792(15) . ? P4 C2 1.8989(14) . ? C1 C3 1.5700(19) . ? C2 C13 1.5718(18) . ? C3 C5 1.527(2) . ? C3 C6 1.532(2) . ? C3 C4 1.534(2) . ? C7 C12 1.5326(18) . ? C7 C8 1.5377(19) . ? C8 C9 1.529(2) . ? C9 C10 1.523(2) . ? C10 C11 1.518(2) . ? C11 C12 1.5317(19) . ? C13 C16 1.528(2) . ? C13 C15 1.531(2) . ? C13 C14 1.537(2) . ? C17 C18 1.536(2) . ? C17 C22 1.536(2) . ? C18 C19 1.529(2) . ? C19 C20 1.520(3) . ? C20 C21 1.518(3) . ? C21 C22 1.524(2) . ? 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 C2 83.19(6) . . ? C1 P1 Cl1 109.60(5) . . ? C2 P1 Cl1 106.77(5) . . ? C1 P2 Cl2 105.81(5) . . ? C1 P2 P4 94.42(5) . . ? Cl2 P2 P4 101.45(3) . . ? C7 P3 C2 112.93(6) . . ? C7 P3 C1 108.41(6) . . ? C2 P3 C1 80.51(6) . . ? C17 P4 C2 111.95(6) . . ? C17 P4 P2 100.19(5) . . ? C2 P4 P2 91.35(5) . . ? C3 C1 P2 117.52(9) . . ? C3 C1 P1 114.97(9) . . ? P2 C1 P1 114.57(7) . . ? C3 C1 P3 121.09(9) . . ? P2 C1 P3 100.91(6) . . ? P1 C1 P3 82.34(6) . . ? C13 C2 P1 113.43(9) . . ? C13 C2 P4 118.30(9) . . ? P1 C2 P4 103.78(7) . . ? C13 C2 P3 118.92(9) . . ? P1 C2 P3 82.50(6) . . ? P4 C2 P3 113.08(7) . . ? C5 C3 C6 108.32(13) . . ? C5 C3 C4 108.34(13) . . ? C6 C3 C4 107.42(12) . . ? C5 C3 C1 110.80(11) . . ? C6 C3 C1 112.87(12) . . ? C4 C3 C1 108.95(11) . . ? C12 C7 C8 108.88(11) . . ? C12 C7 P3 111.21(9) . . ? C8 C7 P3 107.38(9) . . ? C9 C8 C7 110.90(12) . . ? C10 C9 C8 111.26(12) . . ? C11 C10 C9 110.77(12) . . ? C10 C11 C12 111.81(12) . . ? C11 C12 C7 110.71(11) . . ? C16 C13 C15 109.99(13) . . ? C16 C13 C14 107.12(13) . . ? C15 C13 C14 107.72(13) . . ? C16 C13 C2 111.05(12) . . ? C15 C13 C2 109.88(12) . . ? C14 C13 C2 111.00(11) . . ? C18 C17 C22 108.56(12) . . ? C18 C17 P4 110.32(10) . . ? C22 C17 P4 106.88(10) . . ? C19 C18 C17 111.20(14) . . ? C20 C19 C18 111.09(14) . . ? C21 C20 C19 111.02(15) . . ? C20 C21 C22 111.97(15) . . ? C21 C22 C17 112.27(15) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.465 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.044 data_compound_14 _database_code_CSD 187289 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H20 Cl4 P2' _chemical_formula_weight 356.01 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 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 8.1380(16) _cell_length_b 12.136(2) _cell_length_c 16.208(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.58(3) _cell_angle_gamma 90.00 _cell_volume 1593.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.922 _exptl_absorpt_correction_type 'Sortav (blessing)' _exptl_absorpt_correction_T_min 0.77 _exptl_absorpt_correction_T_max 0.93 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27552 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3647 _reflns_number_gt 3378 _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^)+(0.0255P)^2^+0.9510P] 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 3647 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0290 _refine_ls_R_factor_gt 0.0256 _refine_ls_wR_factor_ref 0.0643 _refine_ls_wR_factor_gt 0.0626 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 Cl1 Cl 0.16568(4) 0.00134(3) 0.15192(2) 0.02498(10) Uani 1 1 d . . . Cl2 Cl 0.16533(4) 0.25502(3) 0.17485(2) 0.02389(9) Uani 1 1 d . . . Cl3 Cl -0.42391(4) -0.01215(3) 0.27350(2) 0.02278(9) Uani 1 1 d . . . Cl4 Cl -0.38859(5) 0.24154(3) 0.30682(3) 0.02896(10) Uani 1 1 d . . . P1 P 0.05372(4) 0.11844(3) 0.21671(2) 0.01343(9) Uani 1 1 d . . . P2 P -0.23367(4) 0.10374(3) 0.29351(2) 0.01728(9) Uani 1 1 d . . . C1 C -0.15448(16) 0.11692(11) 0.19767(8) 0.0149(3) Uani 1 1 d . . . C2 C -0.24486(17) 0.11763(12) 0.10786(9) 0.0183(3) Uani 1 1 d . . . C3 C -0.2743(2) -0.00175(13) 0.07781(10) 0.0250(3) Uani 1 1 d . . . H3A H -0.3400 -0.0398 0.1148 0.038 Uiso 1 1 calc R . . H3B H -0.1701 -0.0386 0.0768 0.038 Uiso 1 1 calc R . . H3C H -0.3310 -0.0013 0.0230 0.038 Uiso 1 1 calc R . . C4 C -0.14530(19) 0.17706(14) 0.04516(9) 0.0244(3) Uani 1 1 d . . . H4A H -0.2082 0.1785 -0.0081 0.037 Uiso 1 1 calc R . . H4B H -0.0434 0.1386 0.0409 0.037 Uiso 1 1 calc R . . H4C H -0.1222 0.2511 0.0636 0.037 Uiso 1 1 calc R . . C5 C -0.41163(18) 0.17712(14) 0.10701(10) 0.0268(3) Uani 1 1 d . . . H5A H -0.4663 0.1765 0.0518 0.040 Uiso 1 1 calc R . . H5B H -0.3937 0.2519 0.1250 0.040 Uiso 1 1 calc R . . H5C H -0.4792 0.1402 0.1438 0.040 Uiso 1 1 calc R . . C6 C 0.16199(16) 0.10825(11) 0.32058(8) 0.0142(3) Uani 1 1 d . . . H6 H 0.2790 0.1145 0.3116 0.017 Uiso 1 1 calc R . . C7 C 0.13082(17) 0.20658(12) 0.37707(9) 0.0185(3) Uani 1 1 d . . . H7A H 0.1440 0.2751 0.3476 0.022 Uiso 1 1 calc R . . H7B H 0.0189 0.2035 0.3928 0.022 Uiso 1 1 calc R . . C8 C 0.25393(18) 0.20213(12) 0.45465(9) 0.0204(3) Uani 1 1 d . . . H8A H 0.3651 0.2112 0.4389 0.024 Uiso 1 1 calc R . . H8B H 0.2319 0.2622 0.4914 0.024 Uiso 1 1 calc R . . C9 C 0.24141(19) 0.09306(13) 0.49991(9) 0.0231(3) Uani 1 1 d . . . H9A H 0.1328 0.0867 0.5194 0.028 Uiso 1 1 calc R . . H9B H 0.3226 0.0914 0.5478 0.028 Uiso 1 1 calc R . . C10 C 0.27023(19) -0.00419(13) 0.44343(9) 0.0235(3) Uani 1 1 d . . . H10A H 0.2571 -0.0724 0.4733 0.028 Uiso 1 1 calc R . . H10B H 0.3825 -0.0015 0.4282 0.028 Uiso 1 1 calc R . . C11 C 0.14941(18) -0.00314(12) 0.36446(9) 0.0190(3) Uani 1 1 d . . . H11A H 0.1762 -0.0623 0.3279 0.023 Uiso 1 1 calc R . . H11B H 0.0376 -0.0143 0.3787 0.023 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 0.01944(18) 0.0331(2) 0.02231(18) -0.00895(14) 0.00159(13) 0.00821(14) Cl2 0.02083(17) 0.0278(2) 0.02291(18) 0.00736(14) 0.00143(14) -0.00832(14) Cl3 0.01488(16) 0.02293(19) 0.0307(2) 0.00349(14) 0.00288(14) -0.00374(13) Cl4 0.02281(19) 0.0257(2) 0.0399(2) -0.00841(16) 0.01050(16) 0.00257(14) P1 0.01042(16) 0.01635(18) 0.01346(16) -0.00010(12) 0.00082(12) 0.00005(12) P2 0.01047(16) 0.0239(2) 0.01743(18) -0.00014(14) 0.00136(13) -0.00068(13) C1 0.0106(6) 0.0178(7) 0.0161(6) 0.0001(5) -0.0001(5) 0.0006(5) C2 0.0161(6) 0.0216(7) 0.0165(6) 0.0009(5) -0.0026(5) 0.0013(5) C3 0.0257(8) 0.0261(8) 0.0220(7) -0.0041(6) -0.0039(6) -0.0034(6) C4 0.0240(7) 0.0308(8) 0.0175(7) 0.0044(6) -0.0017(6) -0.0006(6) C5 0.0173(7) 0.0336(9) 0.0280(8) 0.0039(7) -0.0051(6) 0.0067(6) C6 0.0105(6) 0.0174(7) 0.0144(6) 0.0000(5) -0.0014(5) -0.0002(5) C7 0.0197(7) 0.0168(7) 0.0187(7) -0.0019(5) 0.0000(5) 0.0002(5) C8 0.0195(7) 0.0233(7) 0.0180(7) -0.0037(6) -0.0001(5) -0.0032(6) C9 0.0240(7) 0.0301(8) 0.0147(7) 0.0010(6) 0.0002(6) 0.0014(6) C10 0.0256(8) 0.0243(8) 0.0196(7) 0.0034(6) -0.0022(6) 0.0051(6) C11 0.0208(7) 0.0170(7) 0.0186(7) 0.0017(5) -0.0010(5) -0.0002(5) _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 P1 2.0343(6) . ? Cl2 P1 2.0378(6) . ? Cl3 P2 2.0934(6) . ? Cl4 P2 2.1179(6) . ? P1 C1 1.6925(14) . ? P1 C6 1.8269(14) . ? P2 C1 1.7460(15) . ? C1 C2 1.5659(19) . ? C2 C5 1.536(2) . ? C2 C4 1.539(2) . ? C2 C3 1.540(2) . ? C6 C11 1.5355(19) . ? C6 C7 1.5400(19) . ? C7 C8 1.5307(19) . ? C8 C9 1.521(2) . ? C9 C10 1.526(2) . ? C10 C11 1.536(2) . ? 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 C6 123.49(7) . . ? C1 P1 Cl1 112.89(5) . . ? C6 P1 Cl1 103.20(5) . . ? C1 P1 Cl2 114.76(5) . . ? C6 P1 Cl2 99.86(5) . . ? Cl1 P1 Cl2 99.20(3) . . ? C1 P2 Cl3 104.78(5) . . ? C1 P2 Cl4 107.04(5) . . ? Cl3 P2 Cl4 96.18(3) . . ? C2 C1 P1 122.74(10) . . ? C2 C1 P2 130.31(10) . . ? P1 C1 P2 106.76(8) . . ? C5 C2 C4 107.17(12) . . ? C5 C2 C3 109.23(12) . . ? C4 C2 C3 107.92(12) . . ? C5 C2 C1 110.22(12) . . ? C4 C2 C1 112.74(11) . . ? C3 C2 C1 109.47(11) . . ? C11 C6 C7 112.62(11) . . ? C11 C6 P1 116.01(9) . . ? C7 C6 P1 113.76(9) . . ? C8 C7 C6 109.18(11) . . ? C9 C8 C7 110.95(12) . . ? C8 C9 C10 111.24(12) . . ? C9 C10 C11 111.72(12) . . ? C6 C11 C10 109.09(12) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.502 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.055 data_compound_16 _database_code_CSD 187290 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H40 Cl4 P2 Sb2' _chemical_formula_weight 751.78 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' 'Sb' 'Sb' -0.5866 1.5461 '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 10.367(2) _cell_length_b 27.930(6) _cell_length_c 10.889(2) _cell_angle_alpha 90.00 _cell_angle_beta 114.71(3) _cell_angle_gamma 90.00 _cell_volume 2864.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.743 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 2.381 _exptl_absorpt_correction_type 'Sortav (Blessing)' _exptl_absorpt_correction_T_min 0.79 _exptl_absorpt_correction_T_max 0.88 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30376 _diffrn_reflns_av_R_equivalents 0.0800 _diffrn_reflns_av_sigmaI/netI 0.0564 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5560 _reflns_number_gt 4299 _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^)+(0.0507P)^2^+13.4796P] 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 5560 _refine_ls_number_parameters 277 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0727 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1207 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.022 _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 Sb1 Sb 0.45428(5) 0.087396(16) 0.88791(4) 0.03232(14) Uani 1 1 d . . . Sb2 Sb 0.43730(5) 0.040346(15) 0.60647(5) 0.03279(14) Uani 1 1 d . . . Cl1 Cl 0.69625(18) 0.12892(8) 0.59719(17) 0.0475(5) Uani 1 1 d . . . Cl2 Cl 0.4420(2) 0.16907(7) 0.96356(18) 0.0455(4) Uani 1 1 d . . . Cl3 Cl 0.4326(2) -0.02349(6) 0.7526(2) 0.0505(5) Uani 1 1 d . . . Cl4 Cl 0.23663(19) 0.00256(7) 0.4147(2) 0.0519(5) Uani 1 1 d . . . P1 P 0.61218(17) 0.14099(6) 0.73653(16) 0.0272(4) Uani 1 1 d . . . P2 P 0.38107(17) 0.15529(6) 0.63184(16) 0.0261(4) Uani 1 1 d . . . C1 C 0.6326(7) 0.0925(2) 0.8396(6) 0.0305(14) Uani 1 1 d . . . C2 C 0.3216(7) 0.0954(2) 0.6673(6) 0.0292(14) Uani 1 1 d . . . C3 C 0.7768(7) 0.0735(2) 0.9487(6) 0.0303(14) Uani 1 1 d . . . C4 C 0.7627(8) 0.0198(3) 0.9712(8) 0.054(2) Uani 1 1 d . . . H4A H 0.8494 0.0084 1.0417 0.081 Uiso 1 1 calc R . . H4B H 0.7444 0.0027 0.8892 0.081 Uiso 1 1 calc R . . H4C H 0.6857 0.0148 0.9969 0.081 Uiso 1 1 calc R . . C5 C 0.8173(8) 0.0993(3) 1.0824(7) 0.054(2) Uani 1 1 d . . . H5A H 0.9077 0.0878 1.1465 0.081 Uiso 1 1 calc R . . H5B H 0.7466 0.0933 1.1159 0.081 Uiso 1 1 calc R . . H5C H 0.8231 0.1331 1.0693 0.081 Uiso 1 1 calc R . . C6 C 0.8959(8) 0.0779(3) 0.9009(8) 0.0467(19) Uani 1 1 d . . . H6A H 0.9106 0.1110 0.8870 0.070 Uiso 1 1 calc R . . H6B H 0.8699 0.0607 0.8176 0.070 Uiso 1 1 calc R . . H6C H 0.9819 0.0647 0.9682 0.070 Uiso 1 1 calc R . . C7 C 0.6930(8) 0.1997(3) 0.8070(8) 0.052(2) Uani 1 1 d U . . H7 H 0.6669 0.2048 0.8828 0.063 Uiso 1 1 calc R . . C8 C 0.6211(10) 0.2414(3) 0.7105(9) 0.069(3) Uani 1 1 d U . . H8A H 0.5188 0.2384 0.6768 0.082 Uiso 1 1 calc R . . H8B H 0.6458 0.2402 0.6339 0.082 Uiso 1 1 calc R . . C9 C 0.6708(11) 0.2909(4) 0.7868(11) 0.081(3) Uani 1 1 d U . . H9A H 0.6300 0.3171 0.7237 0.097 Uiso 1 1 calc R . . H9B H 0.6375 0.2935 0.8576 0.097 Uiso 1 1 calc R . . C10 C 0.8190(10) 0.2941(3) 0.8432(10) 0.069(3) Uani 1 1 d U . . H10A H 0.8476 0.3242 0.8918 0.083 Uiso 1 1 calc R . . H10B H 0.8505 0.2945 0.7709 0.083 Uiso 1 1 calc R . . C11 C 0.8919(11) 0.2536(3) 0.9384(10) 0.079(3) Uani 1 1 d U . . H11A H 0.8683 0.2550 1.0157 0.095 Uiso 1 1 calc R . . H11B H 0.9940 0.2572 0.9711 0.095 Uiso 1 1 calc R . . C12 C 0.8465(10) 0.2047(3) 0.8676(10) 0.070(3) Uani 1 1 d U . . H12A H 0.8814 0.2016 0.7980 0.084 Uiso 1 1 calc R . . H12B H 0.8884 0.1792 0.9329 0.084 Uiso 1 1 calc R . . C13 C 0.1588(7) 0.0922(2) 0.6343(7) 0.0377(16) Uani 1 1 d . . . C14 C 0.0645(7) 0.0996(3) 0.4849(8) 0.0439(18) Uani 1 1 d . . . H14A H 0.0884 0.0765 0.4325 0.066 Uiso 1 1 calc R . . H14B H 0.0788 0.1313 0.4588 0.066 Uiso 1 1 calc R . . H14C H -0.0331 0.0957 0.4692 0.066 Uiso 1 1 calc R . . C15 C 0.1175(8) 0.1309(3) 0.7125(9) 0.053(2) Uani 1 1 d . . . H15A H 0.1461 0.1618 0.6941 0.080 Uiso 1 1 calc R . . H15B H 0.1641 0.1245 0.8077 0.080 Uiso 1 1 calc R . . H15C H 0.0165 0.1306 0.6843 0.080 Uiso 1 1 calc R . . C16 C 0.1256(7) 0.0432(3) 0.6778(8) 0.0446(18) Uani 1 1 d . . . H16A H 0.0287 0.0427 0.6666 0.067 Uiso 1 1 calc R . . H16B H 0.1875 0.0377 0.7711 0.067 Uiso 1 1 calc R . . H16C H 0.1398 0.0187 0.6231 0.067 Uiso 1 1 calc R . . C17 C 0.3601(7) 0.1648(2) 0.4536(6) 0.0294(14) Uani 1 1 d . . . H17 H 0.4507 0.1783 0.4621 0.035 Uiso 1 1 calc R . . C18 C 0.3312(7) 0.1225(2) 0.3570(6) 0.0334(15) Uani 1 1 d . . . H18A H 0.4091 0.0999 0.3942 0.040 Uiso 1 1 calc R . . H18B H 0.2455 0.1063 0.3495 0.040 Uiso 1 1 calc R . . C19 C 0.3140(9) 0.1376(3) 0.2164(7) 0.0491(19) Uani 1 1 d . . . H19A H 0.4048 0.1487 0.2215 0.059 Uiso 1 1 calc R . . H19B H 0.2859 0.1100 0.1568 0.059 Uiso 1 1 calc R . . C20 C 0.2044(8) 0.1770(3) 0.1569(7) 0.0484(19) Uani 1 1 d . . . H20A H 0.2034 0.1873 0.0714 0.058 Uiso 1 1 calc R . . H20B H 0.1111 0.1645 0.1394 0.058 Uiso 1 1 calc R . . C21 C 0.2362(8) 0.2194(3) 0.2514(7) 0.0473(19) Uani 1 1 d . . . H21A H 0.1611 0.2429 0.2126 0.057 Uiso 1 1 calc R . . H21B H 0.3242 0.2342 0.2598 0.057 Uiso 1 1 calc R . . C22 C 0.2493(8) 0.2056(2) 0.3914(7) 0.0380(16) Uani 1 1 d . . . H22A H 0.1576 0.1950 0.3851 0.046 Uiso 1 1 calc R . . H22B H 0.2778 0.2333 0.4502 0.046 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 Sb1 0.0312(3) 0.0375(3) 0.0303(2) 0.00616(19) 0.01492(19) -0.00350(19) Sb2 0.0288(3) 0.0287(2) 0.0442(3) -0.00031(19) 0.0186(2) 0.00107(18) Cl1 0.0231(9) 0.0816(14) 0.0374(9) 0.0143(9) 0.0123(7) -0.0027(8) Cl2 0.0523(11) 0.0521(11) 0.0400(10) -0.0104(8) 0.0272(9) -0.0044(9) Cl3 0.0476(11) 0.0324(9) 0.0702(13) 0.0135(9) 0.0235(10) -0.0006(8) Cl4 0.0346(10) 0.0499(11) 0.0664(13) -0.0236(10) 0.0164(9) -0.0119(8) P1 0.0220(8) 0.0311(9) 0.0242(8) 0.0034(7) 0.0054(7) -0.0052(7) P2 0.0241(8) 0.0260(8) 0.0260(8) 0.0013(6) 0.0084(7) -0.0013(6) C1 0.025(3) 0.029(3) 0.037(4) 0.006(3) 0.012(3) -0.001(3) C2 0.027(3) 0.026(3) 0.035(3) 0.001(3) 0.014(3) 0.001(3) C3 0.024(3) 0.034(3) 0.029(3) 0.006(3) 0.007(3) 0.000(3) C4 0.038(4) 0.045(4) 0.063(5) 0.027(4) 0.007(4) 0.005(4) C5 0.036(4) 0.072(6) 0.043(4) 0.002(4) 0.007(4) 0.003(4) C6 0.037(4) 0.044(4) 0.056(5) 0.014(4) 0.016(4) 0.011(3) C7 0.043(4) 0.035(3) 0.049(4) 0.014(3) -0.010(3) -0.016(3) C8 0.061(5) 0.052(4) 0.069(5) 0.013(4) 0.004(4) -0.015(4) C9 0.078(5) 0.065(5) 0.088(5) 0.003(4) 0.022(4) 0.001(4) C10 0.068(5) 0.047(4) 0.067(5) 0.004(4) 0.003(4) -0.009(4) C11 0.079(5) 0.056(5) 0.070(5) 0.005(4) 0.000(4) -0.015(4) C12 0.060(5) 0.066(5) 0.074(5) 0.007(4) 0.019(4) -0.003(4) C13 0.027(4) 0.040(4) 0.048(4) -0.003(3) 0.018(3) -0.001(3) C14 0.021(4) 0.052(4) 0.057(5) 0.005(4) 0.015(3) 0.000(3) C15 0.031(4) 0.060(5) 0.077(6) -0.009(4) 0.031(4) 0.000(4) C16 0.025(4) 0.051(4) 0.060(5) 0.007(4) 0.020(3) -0.011(3) C17 0.025(3) 0.034(3) 0.025(3) 0.006(3) 0.005(3) -0.005(3) C18 0.031(4) 0.039(4) 0.027(3) 0.001(3) 0.009(3) 0.003(3) C19 0.052(5) 0.060(5) 0.031(4) 0.001(4) 0.014(3) -0.002(4) C20 0.044(4) 0.062(5) 0.027(4) 0.005(3) 0.003(3) -0.010(4) C21 0.042(4) 0.048(4) 0.038(4) 0.011(3) 0.003(3) -0.004(4) C22 0.039(4) 0.031(4) 0.039(4) 0.012(3) 0.011(3) 0.002(3) _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 Sb1 C1 2.128(6) . ? Sb1 C2 2.225(6) . ? Sb1 Cl2 2.4467(19) . ? Sb2 C2 2.215(6) . ? Sb2 Cl3 2.4041(19) . ? Sb2 Cl4 2.484(2) . ? Cl1 P1 2.069(2) . ? P1 C1 1.714(6) . ? P1 C7 1.855(7) . ? P1 P2 2.217(2) . ? P2 C2 1.878(6) . ? P2 C17 1.879(6) . ? C1 C3 1.562(9) . ? C2 C13 1.574(9) . ? C3 C5 1.518(10) . ? C3 C6 1.532(10) . ? C3 C4 1.537(9) . ? C7 C12 1.452(11) . ? C7 C8 1.536(11) . ? C8 C9 1.585(13) . ? C9 C10 1.399(13) . ? C10 C11 1.506(12) . ? C11 C12 1.544(13) . ? C13 C14 1.521(10) . ? C13 C16 1.532(9) . ? C13 C15 1.545(10) . ? C17 C18 1.527(9) . ? C17 C22 1.556(9) . ? C18 C19 1.525(9) . ? C19 C20 1.518(11) . ? C20 C21 1.513(10) . ? C21 C22 1.524(10) . ? 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 Sb1 C2 86.3(2) . . ? C1 Sb1 Cl2 101.14(17) . . ? C2 Sb1 Cl2 100.04(16) . . ? C2 Sb2 Cl3 98.82(17) . . ? C2 Sb2 Cl4 100.29(17) . . ? Cl3 Sb2 Cl4 89.99(8) . . ? C1 P1 C7 121.1(3) . . ? C1 P1 Cl1 112.1(2) . . ? C7 P1 Cl1 101.0(3) . . ? C1 P1 P2 106.9(2) . . ? C7 P1 P2 104.9(3) . . ? Cl1 P1 P2 110.38(9) . . ? C2 P2 C17 115.6(3) . . ? C2 P2 P1 96.3(2) . . ? C17 P2 P1 101.0(2) . . ? C3 C1 P1 125.7(4) . . ? C3 C1 Sb1 116.3(4) . . ? P1 C1 Sb1 109.4(3) . . ? C13 C2 P2 114.6(4) . . ? C13 C2 Sb2 123.7(4) . . ? P2 C2 Sb2 107.0(3) . . ? C13 C2 Sb1 111.1(4) . . ? P2 C2 Sb1 101.8(3) . . ? Sb2 C2 Sb1 94.9(2) . . ? C5 C3 C6 110.4(6) . . ? C5 C3 C4 108.4(6) . . ? C6 C3 C4 106.0(6) . . ? C5 C3 C1 111.2(6) . . ? C6 C3 C1 111.5(5) . . ? C4 C3 C1 109.2(5) . . ? C12 C7 C8 111.3(7) . . ? C12 C7 P1 119.5(6) . . ? C8 C7 P1 112.4(5) . . ? C7 C8 C9 110.2(7) . . ? C10 C9 C8 110.1(9) . . ? C9 C10 C11 113.4(9) . . ? C10 C11 C12 111.2(8) . . ? C7 C12 C11 111.1(8) . . ? C14 C13 C16 109.0(6) . . ? C14 C13 C15 106.9(6) . . ? C16 C13 C15 107.7(6) . . ? C14 C13 C2 112.6(5) . . ? C16 C13 C2 109.8(5) . . ? C15 C13 C2 110.6(6) . . ? C18 C17 C22 111.7(5) . . ? C18 C17 P2 120.4(4) . . ? C22 C17 P2 107.4(4) . . ? C19 C18 C17 112.6(6) . . ? C20 C19 C18 112.4(6) . . ? C21 C20 C19 111.5(6) . . ? C20 C21 C22 112.6(6) . . ? C21 C22 C17 111.2(6) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.733 (near Sb2) _refine_diff_density_min -1.258 _refine_diff_density_rms 0.165 data_compound_6 _database_code_CSD 187291 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H30 P2' _chemical_formula_weight 368.41 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7667(8) _cell_length_b 9.8576(6) _cell_length_c 12.5778(9) _cell_angle_alpha 87.871(5) _cell_angle_beta 69.191(6) _cell_angle_gamma 69.303(6) _cell_volume 1053.47(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.161 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.209 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 CAD4' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4017 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0604 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 25.23 _reflns_number_total 3777 _reflns_number_gt 2472 _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^)+(0.0390P)^2^+0.8283P] 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 3777 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0993 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1176 _refine_ls_wR_factor_gt 0.0975 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _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 0.03219(9) 0.68249(9) 0.35814(7) 0.0449(2) Uani 1 1 d . . . P2 P 0.32074(9) 0.72875(7) 0.15876(6) 0.0368(2) Uani 1 1 d . . . C1 C 0.2228(3) 0.6578(3) 0.2915(2) 0.0380(6) Uani 1 1 d . . . C2 C 0.3428(4) 0.5551(3) 0.3406(3) 0.0492(8) Uani 1 1 d . . . C3 C 0.4564(4) 0.4232(4) 0.2530(3) 0.0684(10) Uani 1 1 d . . . H3A H 0.5368 0.3648 0.2801 0.103 Uiso 1 1 calc R . . H3B H 0.5038 0.4563 0.1813 0.103 Uiso 1 1 calc R . . H3C H 0.3995 0.3659 0.2427 0.103 Uiso 1 1 calc R . . C4 C 0.4354(5) 0.6403(4) 0.3636(4) 0.0846(13) Uani 1 1 d . . . H4A H 0.5167 0.5762 0.3875 0.127 Uiso 1 1 calc R . . H4B H 0.3657 0.7184 0.4227 0.127 Uiso 1 1 calc R . . H4C H 0.4818 0.6796 0.2950 0.127 Uiso 1 1 calc R . . C5 C 0.2640(5) 0.4970(4) 0.4513(3) 0.0790(12) Uani 1 1 d . . . H5A H 0.3433 0.4301 0.4756 0.119 Uiso 1 1 calc R . . H5B H 0.2018 0.4477 0.4378 0.119 Uiso 1 1 calc R . . H5C H 0.1976 0.5768 0.5096 0.119 Uiso 1 1 calc R . . C6 C -0.0928(3) 0.8232(3) 0.2954(2) 0.0388(6) Uani 1 1 d . . . H6 H -0.0284 0.8689 0.2390 0.047 Uiso 1 1 calc R . . C7 C -0.1709(4) 0.7558(3) 0.2384(3) 0.0469(7) Uani 1 1 d . . . H7A H -0.2231 0.6999 0.2917 0.056 Uiso 1 1 calc R . . H7B H -0.0911 0.6896 0.1726 0.056 Uiso 1 1 calc R . . C8 C -0.2907(4) 0.8722(4) 0.2002(3) 0.0564(8) Uani 1 1 d . . . H8A H -0.2363 0.9200 0.1400 0.068 Uiso 1 1 calc R . . H8B H -0.3429 0.8261 0.1690 0.068 Uiso 1 1 calc R . . C9 C -0.4130(4) 0.9856(4) 0.2977(3) 0.0606(9) Uani 1 1 d . . . H9A H -0.4818 1.0614 0.2687 0.073 Uiso 1 1 calc R . . H9B H -0.4766 0.9405 0.3537 0.073 Uiso 1 1 calc R . . C10 C -0.3359(4) 1.0524(3) 0.3542(3) 0.0564(9) Uani 1 1 d . . . H10A H -0.4160 1.1196 0.4193 0.068 Uiso 1 1 calc R . . H10B H -0.2829 1.1075 0.3006 0.068 Uiso 1 1 calc R . . C11 C -0.2174(3) 0.9375(3) 0.3940(3) 0.0494(8) Uani 1 1 d . . . H11A H -0.2721 0.8897 0.4539 0.059 Uiso 1 1 calc R . . H11B H -0.1662 0.9843 0.4257 0.059 Uiso 1 1 calc R . . C12 C 0.2503(3) 0.9268(3) 0.1919(2) 0.0385(6) Uani 1 1 d . . . C13 C 0.1581(4) 0.9998(3) 0.2999(3) 0.0493(8) Uani 1 1 d . . . H13 H 0.1196 0.9492 0.3600 0.059 Uiso 1 1 calc R . . C14 C 0.1229(4) 1.1484(4) 0.3187(3) 0.0626(9) Uani 1 1 d . . . H14 H 0.0624 1.1961 0.3918 0.075 Uiso 1 1 calc R . . C15 C 0.1761(4) 1.2249(4) 0.2314(3) 0.0642(10) Uani 1 1 d . . . H15 H 0.1492 1.3248 0.2445 0.077 Uiso 1 1 calc R . . C16 C 0.2690(4) 1.1545(3) 0.1244(3) 0.0589(9) Uani 1 1 d . . . H16 H 0.3065 1.2063 0.0648 0.071 Uiso 1 1 calc R . . C17 C 0.3071(4) 1.0060(3) 0.1050(3) 0.0483(8) Uani 1 1 d . . . H17 H 0.3719 0.9585 0.0324 0.058 Uiso 1 1 calc R . . C18 C 0.2282(3) 0.7007(3) 0.0617(2) 0.0353(6) Uani 1 1 d . . . C19 C 0.1562(3) 0.8059(3) 0.0030(2) 0.0426(7) Uani 1 1 d . . . H19 H 0.1436 0.9025 0.0167 0.051 Uiso 1 1 calc R . . C20 C 0.1028(4) 0.7697(3) -0.0758(3) 0.0479(8) Uani 1 1 d . . . H20 H 0.0555 0.8419 -0.1149 0.058 Uiso 1 1 calc R . . C21 C 0.1189(4) 0.6275(3) -0.0971(3) 0.0522(8) Uani 1 1 d . . . H21 H 0.0809 0.6036 -0.1490 0.063 Uiso 1 1 calc R . . C22 C 0.1922(4) 0.5216(3) -0.0403(3) 0.0531(8) Uani 1 1 d . . . H22 H 0.2047 0.4252 -0.0545 0.064 Uiso 1 1 calc R . . C23 C 0.2469(3) 0.5567(3) 0.0368(2) 0.0445(7) Uani 1 1 d . . . H23 H 0.2976 0.4834 0.0735 0.053 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 0.0396(5) 0.0473(5) 0.0417(4) 0.0139(4) -0.0124(4) -0.0122(4) P2 0.0365(4) 0.0308(4) 0.0410(4) 0.0063(3) -0.0134(3) -0.0108(3) C1 0.0447(17) 0.0310(14) 0.0411(16) 0.0067(12) -0.0204(14) -0.0126(13) C2 0.0429(18) 0.0530(19) 0.060(2) 0.0232(15) -0.0305(16) -0.0177(15) C3 0.051(2) 0.050(2) 0.092(3) 0.0229(19) -0.028(2) -0.0053(17) C4 0.102(3) 0.089(3) 0.112(3) 0.039(3) -0.084(3) -0.049(3) C5 0.076(3) 0.091(3) 0.070(2) 0.048(2) -0.039(2) -0.021(2) C6 0.0312(15) 0.0387(15) 0.0377(15) 0.0057(12) -0.0088(13) -0.0064(12) C7 0.0431(18) 0.0444(17) 0.0491(18) -0.0019(14) -0.0147(15) -0.0129(15) C8 0.053(2) 0.060(2) 0.057(2) 0.0048(16) -0.0284(17) -0.0145(17) C9 0.0436(19) 0.059(2) 0.071(2) 0.0058(18) -0.0275(18) -0.0030(16) C10 0.0441(19) 0.0462(18) 0.060(2) -0.0022(15) -0.0147(16) 0.0017(15) C11 0.0419(18) 0.0504(18) 0.0453(17) -0.0035(14) -0.0122(14) -0.0076(14) C12 0.0416(16) 0.0332(14) 0.0468(17) 0.0066(12) -0.0224(14) -0.0148(13) C13 0.059(2) 0.0423(17) 0.0498(18) 0.0012(14) -0.0224(16) -0.0187(15) C14 0.073(2) 0.049(2) 0.067(2) -0.0118(17) -0.033(2) -0.0137(18) C15 0.082(3) 0.0360(18) 0.095(3) 0.0043(19) -0.056(2) -0.0210(18) C16 0.075(2) 0.0426(18) 0.081(3) 0.0226(18) -0.044(2) -0.0329(18) C17 0.056(2) 0.0423(17) 0.0543(19) 0.0104(14) -0.0247(16) -0.0231(15) C18 0.0359(16) 0.0314(14) 0.0312(14) 0.0015(11) -0.0056(12) -0.0104(12) C19 0.0511(19) 0.0311(14) 0.0437(17) 0.0020(12) -0.0182(15) -0.0118(13) C20 0.0476(19) 0.0445(17) 0.0493(18) 0.0068(14) -0.0226(15) -0.0094(14) C21 0.052(2) 0.055(2) 0.0506(19) -0.0075(15) -0.0234(16) -0.0150(16) C22 0.061(2) 0.0373(16) 0.059(2) -0.0051(14) -0.0205(17) -0.0164(15) C23 0.0503(19) 0.0323(15) 0.0480(17) 0.0041(13) -0.0184(15) -0.0115(14) _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 1.678(3) . ? P1 C6 1.856(3) . ? P2 C12 1.835(3) . ? P2 C18 1.835(3) . ? P2 C1 1.855(3) . ? C1 C2 1.552(4) . ? C2 C4 1.532(4) . ? C2 C5 1.532(4) . ? C2 C3 1.535(5) . ? C6 C7 1.523(4) . ? C6 C11 1.534(4) . ? C7 C8 1.525(4) . ? C8 C9 1.516(4) . ? C9 C10 1.507(4) . ? C10 C11 1.522(4) . ? C12 C13 1.386(4) . ? C12 C17 1.387(4) . ? C13 C14 1.390(4) . ? C14 C15 1.362(5) . ? C15 C16 1.368(5) . ? C16 C17 1.386(4) . ? C18 C19 1.383(4) . ? C18 C23 1.398(4) . ? C19 C20 1.381(4) . ? C20 C21 1.379(4) . ? C21 C22 1.376(4) . ? C22 C23 1.367(4) . ? 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 C6 111.18(13) . . ? C12 P2 C18 105.70(12) . . ? C12 P2 C1 106.04(13) . . ? C18 P2 C1 103.07(12) . . ? C2 C1 P1 118.1(2) . . ? C2 C1 P2 112.0(2) . . ? P1 C1 P2 129.80(16) . . ? C4 C2 C5 109.4(3) . . ? C4 C2 C3 109.4(3) . . ? C5 C2 C3 107.5(3) . . ? C4 C2 C1 108.1(2) . . ? C5 C2 C1 112.8(3) . . ? C3 C2 C1 109.5(2) . . ? C7 C6 C11 110.4(2) . . ? C7 C6 P1 110.64(19) . . ? C11 C6 P1 106.75(19) . . ? C6 C7 C8 111.4(2) . . ? C9 C8 C7 112.1(3) . . ? C10 C9 C8 110.9(3) . . ? C9 C10 C11 111.9(3) . . ? C10 C11 C6 111.5(2) . . ? C13 C12 C17 118.0(3) . . ? C13 C12 P2 124.5(2) . . ? C17 C12 P2 117.2(2) . . ? C12 C13 C14 120.2(3) . . ? C15 C14 C13 120.8(3) . . ? C14 C15 C16 119.9(3) . . ? C15 C16 C17 119.9(3) . . ? C16 C17 C12 121.2(3) . . ? C19 C18 C23 117.5(3) . . ? C19 C18 P2 126.0(2) . . ? C23 C18 P2 116.2(2) . . ? C20 C19 C18 121.0(3) . . ? C21 C20 C19 120.7(3) . . ? C22 C21 C20 118.8(3) . . ? C23 C22 C21 120.7(3) . . ? C22 C23 C18 121.4(3) . . ? 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 174.0(2) . . . . ? C6 P1 C1 P2 -9.4(2) . . . . ? C12 P2 C1 C2 -116.3(2) . . . . ? C18 P2 C1 C2 132.8(2) . . . . ? C12 P2 C1 P1 67.0(2) . . . . ? C18 P2 C1 P1 -43.9(2) . . . . ? P1 C1 C2 C4 -124.8(3) . . . . ? P2 C1 C2 C4 58.1(3) . . . . ? P1 C1 C2 C5 -3.6(4) . . . . ? P2 C1 C2 C5 179.2(2) . . . . ? P1 C1 C2 C3 116.0(2) . . . . ? P2 C1 C2 C3 -61.1(3) . . . . ? C1 P1 C6 C7 114.5(2) . . . . ? C1 P1 C6 C11 -125.4(2) . . . . ? C11 C6 C7 C8 54.5(3) . . . . ? P1 C6 C7 C8 172.5(2) . . . . ? C6 C7 C8 C9 -55.1(4) . . . . ? C7 C8 C9 C10 54.8(4) . . . . ? C8 C9 C10 C11 -55.1(4) . . . . ? C9 C10 C11 C6 55.7(4) . . . . ? C7 C6 C11 C10 -54.9(3) . . . . ? P1 C6 C11 C10 -175.2(2) . . . . ? C18 P2 C12 C13 116.1(3) . . . . ? C1 P2 C12 C13 7.1(3) . . . . ? C18 P2 C12 C17 -70.9(2) . . . . ? C1 P2 C12 C17 -179.9(2) . . . . ? C17 C12 C13 C14 0.9(4) . . . . ? P2 C12 C13 C14 173.8(2) . . . . ? C12 C13 C14 C15 1.1(5) . . . . ? C13 C14 C15 C16 -1.9(5) . . . . ? C14 C15 C16 C17 0.8(5) . . . . ? C15 C16 C17 C12 1.2(5) . . . . ? C13 C12 C17 C16 -2.0(4) . . . . ? P2 C12 C17 C16 -175.5(2) . . . . ? C12 P2 C18 C19 15.4(3) . . . . ? C1 P2 C18 C19 126.5(2) . . . . ? C12 P2 C18 C23 -171.4(2) . . . . ? C1 P2 C18 C23 -60.3(2) . . . . ? C23 C18 C19 C20 1.0(4) . . . . ? P2 C18 C19 C20 174.1(2) . . . . ? C18 C19 C20 C21 0.5(5) . . . . ? C19 C20 C21 C22 -1.4(5) . . . . ? C20 C21 C22 C23 0.6(5) . . . . ? C21 C22 C23 C18 1.0(5) . . . . ? C19 C18 C23 C22 -1.8(4) . . . . ? P2 C18 C23 C22 -175.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.23 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.306 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.051 data_compound_7 _database_code_CSD 187292 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H51 P3' _chemical_formula_weight 480.60 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.012(4) _cell_length_b 10.877(4) _cell_length_c 15.047(7) _cell_angle_alpha 72.31(3) _cell_angle_beta 89.79(3) _cell_angle_gamma 66.25(3) _cell_volume 1415.7(10) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.127 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.224 _exptl_absorpt_correction_type Diffabs _exptl_absorpt_correction_T_min 0.71 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 CAD4' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5977 _diffrn_reflns_av_R_equivalents 0.0835 _diffrn_reflns_av_sigmaI/netI 0.1966 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 26.29 _reflns_number_total 5751 _reflns_number_gt 2931 _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^)+(0.0456P)^2^+0.9713P] 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 5751 _refine_ls_number_parameters 286 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1856 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1449 _refine_ls_wR_factor_gt 0.1122 _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_restrained_S_all 0.959 _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 0.00410(11) 0.47881(11) 0.78903(8) 0.0194(3) Uani 1 1 d . . . P2 P 0.08570(11) 0.42447(11) 0.66398(7) 0.0188(3) Uani 1 1 d . . . P3 P 0.33042(11) 0.27614(11) 0.84859(8) 0.0194(3) Uani 1 1 d . . . C1 C 0.1987(4) 0.4662(4) 0.8010(3) 0.0189(9) Uani 1 1 d . . . C2 C 0.2631(4) 0.3954(4) 0.7241(3) 0.0178(9) Uani 1 1 d . . . C3 C -0.1405(4) 0.6651(4) 0.7242(3) 0.0215(9) Uani 1 1 d . . . H3 H -0.0962 0.7193 0.6797 0.026 Uiso 1 1 calc R . . C4 C -0.2124(5) 0.7431(4) 0.7929(3) 0.0341(11) Uani 1 1 d . . . H4A H -0.2492 0.6851 0.8395 0.041 Uiso 1 1 calc R . . H4B H -0.1390 0.7568 0.8257 0.041 Uiso 1 1 calc R . . C5 C -0.3385(5) 0.8869(4) 0.7424(3) 0.0345(11) Uani 1 1 d . . . H5A H -0.3833 0.9323 0.7880 0.041 Uiso 1 1 calc R . . H5B H -0.3008 0.9476 0.6991 0.041 Uiso 1 1 calc R . . C6 C -0.4530(5) 0.8696(5) 0.6889(3) 0.0368(12) Uani 1 1 d . . . H6A H -0.4979 0.8173 0.7330 0.044 Uiso 1 1 calc R . . H6B H -0.5296 0.9627 0.6544 0.044 Uiso 1 1 calc R . . C7 C -0.3872(5) 0.7918(5) 0.6210(3) 0.0358(11) Uani 1 1 d . . . H7A H -0.3530 0.8496 0.5722 0.043 Uiso 1 1 calc R . . H7B H -0.4624 0.7769 0.5910 0.043 Uiso 1 1 calc R . . C8 C -0.2584(4) 0.6480(4) 0.6709(3) 0.0286(10) Uani 1 1 d . . . H8A H -0.2150 0.6031 0.6248 0.034 Uiso 1 1 calc R . . H8B H -0.2947 0.5864 0.7148 0.034 Uiso 1 1 calc R . . C9 C 0.0810(4) 0.2511(4) 0.6701(3) 0.0193(9) Uani 1 1 d . . . H9 H 0.1617 0.1734 0.7172 0.023 Uiso 1 1 calc R . . C10 C -0.0656(4) 0.2510(4) 0.7002(3) 0.0276(10) Uani 1 1 d . . . H10A H -0.0749 0.2627 0.7616 0.033 Uiso 1 1 calc R . . H10B H -0.1464 0.3308 0.6558 0.033 Uiso 1 1 calc R . . C11 C -0.0756(5) 0.1126(4) 0.7046(3) 0.0308(11) Uani 1 1 d . . . H11A H -0.0008 0.0337 0.7535 0.037 Uiso 1 1 calc R . . H11B H -0.1711 0.1179 0.7210 0.037 Uiso 1 1 calc R . . C12 C -0.0549(5) 0.0854(5) 0.6123(3) 0.0364(12) Uani 1 1 d . . . H12A H -0.1372 0.1574 0.5652 0.044 Uiso 1 1 calc R . . H12B H -0.0539 -0.0066 0.6191 0.044 Uiso 1 1 calc R . . C13 C 0.0869(6) 0.0879(5) 0.5795(3) 0.0405(13) Uani 1 1 d . . . H13A H 0.0925 0.0787 0.5174 0.049 Uiso 1 1 calc R . . H13B H 0.1696 0.0073 0.6220 0.049 Uiso 1 1 calc R . . C14 C 0.0981(5) 0.2252(5) 0.5760(3) 0.0331(11) Uani 1 1 d . . . H14A H 0.1930 0.2201 0.5584 0.040 Uiso 1 1 calc R . . H14B H 0.0223 0.3048 0.5281 0.040 Uiso 1 1 calc R . . C15 C 0.2303(4) 0.5717(4) 0.8399(3) 0.0241(10) Uani 1 1 d . . . C16 C 0.3935(5) 0.5365(5) 0.8593(4) 0.0454(13) Uani 1 1 d . . . H16A H 0.4322 0.5555 0.8007 0.068 Uiso 1 1 calc R . . H16B H 0.4460 0.4378 0.8961 0.068 Uiso 1 1 calc R . . H16C H 0.4047 0.5942 0.8934 0.068 Uiso 1 1 calc R . . C17 C 0.1694(5) 0.5610(5) 0.9339(3) 0.0361(11) Uani 1 1 d . . . H17A H 0.0674 0.5792 0.9248 0.054 Uiso 1 1 calc R . . H17B H 0.1785 0.6299 0.9580 0.054 Uiso 1 1 calc R . . H17C H 0.2238 0.4673 0.9781 0.054 Uiso 1 1 calc R . . C18 C 0.1550(5) 0.7248(4) 0.7724(3) 0.0370(12) Uani 1 1 d . . . H18A H 0.0501 0.7582 0.7704 0.055 Uiso 1 1 calc R . . H18B H 0.1808 0.7279 0.7105 0.055 Uiso 1 1 calc R . . H18C H 0.1868 0.7845 0.7939 0.055 Uiso 1 1 calc R . . C19 C 0.3795(4) 0.4105(4) 0.6580(3) 0.0240(9) Uani 1 1 d . . . C20 C 0.3314(5) 0.5657(5) 0.5977(4) 0.0509(15) Uani 1 1 d . . . H20A H 0.3394 0.6188 0.6364 0.076 Uiso 1 1 calc R . . H20B H 0.2310 0.6046 0.5694 0.076 Uiso 1 1 calc R . . H20C H 0.3934 0.5716 0.5493 0.076 Uiso 1 1 calc R . . C21 C 0.3856(6) 0.3270(6) 0.5925(4) 0.0506(15) Uani 1 1 d . . . H21A H 0.2906 0.3655 0.5562 0.076 Uiso 1 1 calc R . . H21B H 0.4128 0.2290 0.6289 0.076 Uiso 1 1 calc R . . H21C H 0.4572 0.3335 0.5509 0.076 Uiso 1 1 calc R . . C22 C 0.5349(5) 0.3510(6) 0.7075(4) 0.0538(15) Uani 1 1 d . . . H22A H 0.5350 0.3957 0.7536 0.081 Uiso 1 1 calc R . . H22B H 0.5981 0.3693 0.6622 0.081 Uiso 1 1 calc R . . H22C H 0.5699 0.2502 0.7382 0.081 Uiso 1 1 calc R . . C23 C 0.2328(4) 0.1617(4) 0.8955(3) 0.0172(8) Uani 1 1 d . . . H23 H 0.1406 0.1961 0.8544 0.021 Uiso 1 1 calc R . . C24 C 0.2008(4) 0.1689(4) 0.9937(3) 0.0216(9) Uani 1 1 d . . . H24A H 0.2914 0.1462 1.0312 0.026 Uiso 1 1 calc R . . H24B H 0.1325 0.2650 0.9884 0.026 Uiso 1 1 calc R . . C25 C 0.1358(5) 0.0663(4) 1.0430(3) 0.0274(10) Uani 1 1 d . . . H25A H 0.0407 0.0943 1.0086 0.033 Uiso 1 1 calc R . . H25B H 0.1208 0.0707 1.1058 0.033 Uiso 1 1 calc R . . C26 C 0.2367(5) -0.0857(4) 1.0494(3) 0.0296(10) Uani 1 1 d . . . H26A H 0.3280 -0.1175 1.0894 0.035 Uiso 1 1 calc R . . H26B H 0.1898 -0.1481 1.0777 0.035 Uiso 1 1 calc R . . C27 C 0.2699(5) -0.0949(4) 0.9526(3) 0.0283(10) Uani 1 1 d . . . H27A H 0.1799 -0.0744 0.9154 0.034 Uiso 1 1 calc R . . H27B H 0.3393 -0.1911 0.9591 0.034 Uiso 1 1 calc R . . C28 C 0.3338(4) 0.0086(4) 0.9015(3) 0.0211(9) Uani 1 1 d . . . H28A H 0.3466 0.0043 0.8384 0.025 Uiso 1 1 calc R . . H28B H 0.4298 -0.0191 0.9345 0.025 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 0.0199(6) 0.0178(5) 0.0190(6) -0.0060(5) 0.0028(5) -0.0064(4) P2 0.0205(6) 0.0175(5) 0.0182(6) -0.0057(4) 0.0023(5) -0.0080(4) P3 0.0195(6) 0.0172(5) 0.0197(6) -0.0036(5) 0.0017(5) -0.0077(5) C1 0.017(2) 0.015(2) 0.022(2) -0.0042(17) -0.0006(17) -0.0060(16) C2 0.016(2) 0.0137(19) 0.018(2) -0.0025(17) -0.0004(17) -0.0020(16) C3 0.019(2) 0.021(2) 0.023(2) -0.0081(18) 0.0022(18) -0.0060(18) C4 0.026(2) 0.035(3) 0.039(3) -0.021(2) 0.001(2) -0.003(2) C5 0.029(3) 0.026(2) 0.046(3) -0.021(2) 0.006(2) -0.002(2) C6 0.027(3) 0.031(3) 0.044(3) -0.014(2) 0.003(2) -0.003(2) C7 0.026(2) 0.035(3) 0.040(3) -0.018(2) -0.005(2) -0.003(2) C8 0.026(2) 0.028(2) 0.034(3) -0.017(2) 0.001(2) -0.008(2) C9 0.023(2) 0.0149(19) 0.017(2) -0.0045(17) -0.0021(17) -0.0049(17) C10 0.027(2) 0.024(2) 0.034(3) -0.010(2) 0.000(2) -0.0114(19) C11 0.033(3) 0.020(2) 0.039(3) -0.003(2) 0.000(2) -0.015(2) C12 0.055(3) 0.025(2) 0.029(3) -0.004(2) -0.010(2) -0.020(2) C13 0.071(4) 0.036(3) 0.029(3) -0.021(2) 0.013(3) -0.029(3) C14 0.047(3) 0.036(3) 0.023(3) -0.013(2) 0.003(2) -0.021(2) C15 0.029(2) 0.020(2) 0.026(2) -0.0113(18) -0.0025(19) -0.0092(18) C16 0.038(3) 0.039(3) 0.074(4) -0.030(3) 0.001(3) -0.022(2) C17 0.052(3) 0.033(3) 0.029(3) -0.017(2) 0.001(2) -0.019(2) C18 0.047(3) 0.022(2) 0.045(3) -0.013(2) -0.002(2) -0.016(2) C19 0.022(2) 0.022(2) 0.024(2) -0.0042(19) 0.0059(19) -0.0081(18) C20 0.046(3) 0.041(3) 0.047(3) 0.009(3) 0.021(3) -0.018(3) C21 0.056(3) 0.069(4) 0.056(4) -0.040(3) 0.039(3) -0.042(3) C22 0.033(3) 0.090(4) 0.040(3) -0.014(3) 0.014(3) -0.033(3) C23 0.0146(19) 0.017(2) 0.018(2) -0.0048(17) 0.0027(16) -0.0059(16) C24 0.023(2) 0.025(2) 0.019(2) -0.0079(18) 0.0058(18) -0.0123(18) C25 0.031(2) 0.036(3) 0.018(2) -0.008(2) 0.0057(19) -0.018(2) C26 0.036(3) 0.027(2) 0.020(2) 0.0060(19) -0.006(2) -0.018(2) C27 0.031(2) 0.017(2) 0.034(3) -0.0054(19) 0.000(2) -0.0097(19) C28 0.025(2) 0.020(2) 0.018(2) -0.0074(18) 0.0055(18) -0.0094(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 C3 1.898(4) . ? P1 C1 1.902(4) . ? P1 P2 2.1986(17) . ? P2 C2 1.860(4) . ? P2 C9 1.880(4) . ? P3 C1 1.854(4) . ? P3 C23 1.856(4) . ? P3 C2 1.864(4) . ? C1 C15 1.569(5) . ? C1 C2 1.576(5) . ? C2 C19 1.556(5) . ? C3 C4 1.531(5) . ? C3 C8 1.532(5) . ? C4 C5 1.521(6) . ? C5 C6 1.507(6) . ? C6 C7 1.505(6) . ? C7 C8 1.531(5) . ? C9 C14 1.520(5) . ? C9 C10 1.535(5) . ? C10 C11 1.531(5) . ? C11 C12 1.503(6) . ? C12 C13 1.510(6) . ? C13 C14 1.527(5) . ? C15 C16 1.527(6) . ? C15 C18 1.530(5) . ? C15 C17 1.530(6) . ? C19 C22 1.516(6) . ? C19 C21 1.517(6) . ? C19 C20 1.524(5) . ? C23 C24 1.529(5) . ? C23 C28 1.535(5) . ? C24 C25 1.516(5) . ? C25 C26 1.524(6) . ? C26 C27 1.516(6) . ? C27 C28 1.523(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 C1 113.89(17) . . ? C3 P1 P2 97.01(14) . . ? C1 P1 P2 78.17(13) . . ? C2 P2 C9 111.39(17) . . ? C2 P2 P1 81.79(13) . . ? C9 P2 P1 109.16(13) . . ? C1 P3 C23 110.93(17) . . ? C1 P3 C2 50.17(17) . . ? C23 P3 C2 114.98(17) . . ? C15 C1 C2 133.3(3) . . ? C15 C1 P3 116.7(3) . . ? C2 C1 P3 65.25(19) . . ? C15 C1 P1 120.0(3) . . ? C2 C1 P1 99.8(2) . . ? P3 C1 P1 109.06(19) . . ? C19 C2 C1 131.5(3) . . ? C19 C2 P2 115.0(3) . . ? C1 C2 P2 97.8(2) . . ? C19 C2 P3 118.1(3) . . ? C1 C2 P3 64.59(19) . . ? P2 C2 P3 120.6(2) . . ? C4 C3 C8 108.8(3) . . ? C4 C3 P1 111.2(3) . . ? C8 C3 P1 106.6(3) . . ? C5 C4 C3 111.6(4) . . ? C6 C5 C4 110.6(4) . . ? C7 C6 C5 111.6(4) . . ? C6 C7 C8 111.4(4) . . ? C7 C8 C3 111.3(3) . . ? C14 C9 C10 109.0(3) . . ? C14 C9 P2 112.0(3) . . ? C10 C9 P2 109.6(3) . . ? C11 C10 C9 111.5(3) . . ? C12 C11 C10 111.7(4) . . ? C11 C12 C13 111.4(4) . . ? C12 C13 C14 111.8(4) . . ? C9 C14 C13 112.1(4) . . ? C16 C15 C18 107.3(4) . . ? C16 C15 C17 107.1(4) . . ? C18 C15 C17 109.8(3) . . ? C16 C15 C1 114.5(3) . . ? C18 C15 C1 111.6(3) . . ? C17 C15 C1 106.4(3) . . ? C22 C19 C21 106.5(4) . . ? C22 C19 C20 109.8(4) . . ? C21 C19 C20 107.7(4) . . ? C22 C19 C2 115.0(3) . . ? C21 C19 C2 107.3(3) . . ? C20 C19 C2 110.3(3) . . ? C24 C23 C28 110.4(3) . . ? C24 C23 P3 107.2(3) . . ? C28 C23 P3 108.6(2) . . ? C25 C24 C23 111.6(3) . . ? C24 C25 C26 111.2(3) . . ? C27 C26 C25 110.8(3) . . ? C26 C27 C28 112.1(3) . . ? C27 C28 C23 111.3(3) . . ? 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 C3 P1 P2 C2 122.90(17) . . . . ? C1 P1 P2 C2 9.87(16) . . . . ? C3 P1 P2 C9 -127.22(18) . . . . ? C1 P1 P2 C9 119.75(18) . . . . ? C23 P3 C1 C15 126.5(3) . . . . ? C2 P3 C1 C15 -127.8(4) . . . . ? C23 P3 C1 C2 -105.6(2) . . . . ? C23 P3 C1 P1 -13.4(3) . . . . ? C2 P3 C1 P1 92.3(3) . . . . ? C3 P1 C1 C15 50.4(3) . . . . ? P2 P1 C1 C15 142.9(3) . . . . ? C3 P1 C1 C2 -104.2(2) . . . . ? P2 P1 C1 C2 -11.73(19) . . . . ? C3 P1 C1 P3 -171.30(19) . . . . ? P2 P1 C1 P3 -78.80(18) . . . . ? C15 C1 C2 C19 -1.8(6) . . . . ? P3 C1 C2 C19 -106.0(4) . . . . ? P1 C1 C2 C19 147.5(3) . . . . ? C15 C1 C2 P2 -135.6(4) . . . . ? P3 C1 C2 P2 120.29(19) . . . . ? P1 C1 C2 P2 13.7(2) . . . . ? C15 C1 C2 P3 104.1(4) . . . . ? P1 C1 C2 P3 -106.56(18) . . . . ? C9 P2 C2 C19 97.4(3) . . . . ? P1 P2 C2 C19 -155.1(3) . . . . ? C9 P2 C2 C1 -119.2(2) . . . . ? P1 P2 C2 C1 -11.80(19) . . . . ? C9 P2 C2 P3 -54.2(3) . . . . ? P1 P2 C2 P3 53.2(2) . . . . ? C1 P3 C2 C19 125.3(4) . . . . ? C23 P3 C2 C19 -137.5(3) . . . . ? C23 P3 C2 C1 97.2(2) . . . . ? C1 P3 C2 P2 -83.9(3) . . . . ? C23 P3 C2 P2 13.3(3) . . . . ? C1 P1 C3 C4 -94.4(3) . . . . ? P2 P1 C3 C4 -174.5(3) . . . . ? C1 P1 C3 C8 147.2(3) . . . . ? P2 P1 C3 C8 67.1(3) . . . . ? C8 C3 C4 C5 -57.4(5) . . . . ? P1 C3 C4 C5 -174.5(3) . . . . ? C3 C4 C5 C6 57.7(5) . . . . ? C4 C5 C6 C7 -55.9(5) . . . . ? C5 C6 C7 C8 55.1(5) . . . . ? C6 C7 C8 C3 -55.7(5) . . . . ? C4 C3 C8 C7 56.0(5) . . . . ? P1 C3 C8 C7 176.1(3) . . . . ? C2 P2 C9 C14 -106.0(3) . . . . ? P1 P2 C9 C14 165.5(3) . . . . ? C2 P2 C9 C10 132.9(3) . . . . ? P1 P2 C9 C10 44.4(3) . . . . ? C14 C9 C10 C11 56.2(4) . . . . ? P2 C9 C10 C11 179.1(3) . . . . ? C9 C10 C11 C12 -56.4(5) . . . . ? C10 C11 C12 C13 54.4(5) . . . . ? C11 C12 C13 C14 -53.8(5) . . . . ? C10 C9 C14 C13 -55.9(5) . . . . ? P2 C9 C14 C13 -177.3(3) . . . . ? C12 C13 C14 C9 55.5(5) . . . . ? C2 C1 C15 C16 -43.9(6) . . . . ? P3 C1 C15 C16 36.2(5) . . . . ? P1 C1 C15 C16 171.6(3) . . . . ? C2 C1 C15 C18 78.2(5) . . . . ? P3 C1 C15 C18 158.4(3) . . . . ? P1 C1 C15 C18 -66.3(4) . . . . ? C2 C1 C15 C17 -162.0(4) . . . . ? P3 C1 C15 C17 -81.9(4) . . . . ? P1 C1 C15 C17 53.5(4) . . . . ? C1 C2 C19 C22 67.2(5) . . . . ? P2 C2 C19 C22 -165.0(3) . . . . ? P3 C2 C19 C22 -12.6(5) . . . . ? C1 C2 C19 C21 -174.6(4) . . . . ? P2 C2 C19 C21 -46.8(4) . . . . ? P3 C2 C19 C21 105.6(4) . . . . ? C1 C2 C19 C20 -57.6(5) . . . . ? P2 C2 C19 C20 70.3(4) . . . . ? P3 C2 C19 C20 -137.3(3) . . . . ? C1 P3 C23 C24 -80.3(3) . . . . ? C2 P3 C23 C24 -135.0(3) . . . . ? C1 P3 C23 C28 160.4(3) . . . . ? C2 P3 C23 C28 105.8(3) . . . . ? C28 C23 C24 C25 -55.7(4) . . . . ? P3 C23 C24 C25 -173.8(3) . . . . ? C23 C24 C25 C26 56.6(4) . . . . ? C24 C25 C26 C27 -55.7(5) . . . . ? C25 C26 C27 C28 55.1(5) . . . . ? C26 C27 C28 C23 -54.9(5) . . . . ? C24 C23 C28 C27 54.4(4) . . . . ? P3 C23 C28 C27 171.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.29 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.514 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.084 data_compound_9 _database_code_CSD 187293 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H40 Cl P3' _chemical_formula_weight 432.90 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 orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.124(2) _cell_length_b 23.941(5) _cell_length_c 9.791(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2373.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.368 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 CAD4' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4176 _diffrn_reflns_av_R_equivalents 0.0841 _diffrn_reflns_av_sigmaI/netI 0.1626 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 25.24 _reflns_number_total 2135 _reflns_number_gt 951 _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^)+(0.0843P)^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 2135 _refine_ls_number_parameters 155 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.1532 _refine_ls_R_factor_gt 0.0670 _refine_ls_wR_factor_ref 0.1877 _refine_ls_wR_factor_gt 0.1625 _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_restrained_S_all 0.949 _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 Cl1 Cl 0.0000 0.20563(7) 0.2500 0.0509(6) Uani 1 2 d S . . P1 P 0.0591(3) 0.28510(10) 0.1844(3) 0.0278(6) Uani 0.50 1 d P . . P2 P 0.0457(2) 0.39047(10) 0.1998(3) 0.0253(6) Uani 0.50 1 d P . . P2' P 0.1006(3) 0.32904(10) 0.1301(3) 0.0267(6) Uani 0.50 1 d P . . C1 C 0.1642(5) 0.3953(2) 0.0562(5) 0.0305(12) Uani 1 1 d . . . C2 C 0.1060(15) 0.4327(12) -0.0532(19) 0.054(5) Uani 0.51(3) 1 d PU A 1 H2A H 0.0292 0.4139 -0.0906 0.064 Uiso 0.51(3) 1 calc PR A 1 H2B H 0.0747 0.4665 -0.0090 0.064 Uiso 0.51(3) 1 calc PR A 1 C2A C 0.1218(14) 0.4035(10) -0.0843(15) 0.036(5) Uani 0.49(3) 1 d PU A 2 H2A1 H 0.0276 0.4108 -0.0836 0.043 Uiso 0.49(3) 1 calc PR A 2 H2A2 H 0.1353 0.3687 -0.1330 0.043 Uiso 0.49(3) 1 calc PR A 2 C3 C 0.1870(6) 0.4489(3) -0.1636(7) 0.068(2) Uani 1 1 d . . . H3A H 0.1514 0.4834 -0.2004 0.082 Uiso 1 1 calc R A 1 H3B H 0.1781 0.4207 -0.2342 0.082 Uiso 1 1 calc R A 1 C4 C 0.3296(5) 0.4576(2) -0.1396(5) 0.0418(15) Uani 1 1 d . A . H4A H 0.3439 0.4964 -0.1154 0.050 Uiso 1 1 calc R B 1 H4B H 0.3766 0.4506 -0.2243 0.050 Uiso 1 1 calc R B 1 C5 C 0.3877(15) 0.4215(10) -0.030(2) 0.042(5) Uani 0.49(4) 1 d PU A 1 H5A H 0.4222 0.3881 -0.0733 0.051 Uiso 0.49(4) 1 calc PR A 1 H5B H 0.4623 0.4414 0.0088 0.051 Uiso 0.49(4) 1 calc PR A 1 C5A C 0.3749(17) 0.4471(11) 0.0034(19) 0.044(5) Uani 0.51(4) 1 d PU A 2 H5A1 H 0.4677 0.4369 0.0004 0.053 Uiso 0.51(4) 1 calc PR A 2 H5A2 H 0.3682 0.4818 0.0539 0.053 Uiso 0.51(4) 1 calc PR A 2 C6 C 0.3054(6) 0.4044(3) 0.0792(6) 0.068(2) Uani 1 1 d . A . H6A H 0.3136 0.4322 0.1508 0.081 Uiso 1 1 calc R C 1 H6B H 0.3416 0.3699 0.1150 0.081 Uiso 1 1 calc R C 1 C7 C -0.0843(5) 0.3327(2) 0.1736(5) 0.0269(12) Uani 1 1 d . . . C8 C -0.1958(5) 0.3289(2) 0.0712(5) 0.0300(12) Uani 1 1 d . A . C9 C -0.2503(5) 0.3866(2) 0.0355(6) 0.0429(15) Uani 1 1 d . . . H9A H -0.3135 0.3832 -0.0372 0.064 Uiso 1 1 calc R A . H9B H -0.1792 0.4104 0.0068 0.064 Uiso 1 1 calc R . . H9C H -0.2924 0.4024 0.1143 0.064 Uiso 1 1 calc R . . C10 C -0.3082(5) 0.2934(2) 0.1290(5) 0.0411(14) Uani 1 1 d . . . H10A H -0.3788 0.2915 0.0638 0.062 Uiso 1 1 calc R A . H10B H -0.3400 0.3100 0.2120 0.062 Uiso 1 1 calc R . . H10C H -0.2763 0.2564 0.1477 0.062 Uiso 1 1 calc R . . C11 C -0.1448(6) 0.3000(2) -0.0589(5) 0.0447(15) Uani 1 1 d . . . H11A H -0.2140 0.2988 -0.1259 0.067 Uiso 1 1 calc R A . H11B H -0.1175 0.2626 -0.0373 0.067 Uiso 1 1 calc R . . H11C H -0.0710 0.3205 -0.0947 0.067 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 0.0574(13) 0.0265(9) 0.0689(16) 0.000 -0.0040(13) 0.000 P1 0.0311(14) 0.0265(13) 0.0259(15) -0.0027(12) 0.0009(13) 0.0024(12) P2 0.0247(14) 0.0267(12) 0.0246(14) 0.0024(11) -0.0017(11) 0.0008(11) P2' 0.0284(15) 0.0274(14) 0.0243(13) 0.0015(13) 0.0011(13) -0.0025(12) C1 0.025(3) 0.037(3) 0.029(3) 0.015(2) 0.000(2) -0.001(2) C2 0.044(7) 0.062(9) 0.055(8) 0.001(7) -0.015(6) 0.000(7) C2A 0.026(7) 0.044(8) 0.036(7) 0.003(5) -0.008(5) -0.014(6) C3 0.055(4) 0.094(5) 0.056(4) 0.040(4) -0.006(4) -0.022(4) C4 0.047(4) 0.047(3) 0.031(3) 0.003(3) 0.009(3) -0.002(3) C5 0.027(6) 0.043(8) 0.057(8) -0.007(6) 0.002(6) 0.005(6) C5A 0.036(7) 0.055(9) 0.041(7) 0.003(6) -0.001(6) -0.005(6) C6 0.044(4) 0.101(5) 0.058(4) 0.038(4) -0.017(4) -0.033(4) C7 0.027(3) 0.030(3) 0.023(3) 0.000(2) -0.001(2) 0.001(2) C8 0.028(3) 0.036(3) 0.026(3) -0.004(2) -0.006(2) -0.006(2) C9 0.038(3) 0.048(3) 0.042(3) 0.006(3) -0.018(3) 0.005(3) C10 0.037(3) 0.058(3) 0.028(3) 0.006(3) -0.011(3) -0.015(3) C11 0.042(4) 0.070(4) 0.022(3) -0.005(3) -0.009(3) 0.000(3) _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 P1 2.095(3) . ? Cl1 P1 2.095(3) 3 ? P1 P2' 1.251(3) . ? P1 P1 1.756(5) 3 ? P1 C7 1.816(5) 3 ? P1 C7 1.848(5) . ? P1 P2 2.531(3) . ? P1 P2' 2.650(4) 3 ? P2 P2 1.350(5) 3 ? P2 P2' 1.714(3) . ? P2 C1 1.852(5) . ? P2 C7 1.898(5) 3 ? P2 C7 1.926(5) . ? P2 P2' 2.671(4) 3 ? P2' C1 1.858(5) . ? P2' C7 1.922(5) . ? P2' C7 1.931(5) 3 ? P2' P1 2.650(4) 3 ? P2' P2 2.671(4) 3 ? C1 C2A 1.454(13) . ? C1 C6 1.463(7) . ? C1 C2 1.516(16) . ? C2 C3 1.410(16) . ? C2A C3 1.490(14) . ? C3 C4 1.478(8) . ? C4 C5A 1.496(15) . ? C4 C5 1.498(16) . ? C5 C6 1.416(16) . ? C5A C6 1.445(16) . ? C7 C8 1.513(6) . ? C7 P1 1.816(5) 3 ? C7 P2 1.898(5) 3 ? C7 P2' 1.931(5) 3 ? C8 C9 1.528(6) . ? C8 C10 1.528(6) . ? C8 C11 1.539(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag P1 Cl1 P1 49.55(15) . 3 ? P2' P1 P1 122.68(17) . 3 ? P2' P1 C7 75.5(2) . 3 ? P1 P1 C7 62.3(2) 3 3 ? P2' P1 C7 73.8(2) . . ? P1 P1 C7 60.45(19) 3 . ? C7 P1 C7 76.5(3) 3 . ? P2' P1 Cl1 171.7(2) . . ? P1 P1 Cl1 65.23(7) 3 . ? C7 P1 Cl1 112.0(2) 3 . ? C7 P1 Cl1 110.7(2) . . ? P2' P1 P2 37.38(15) . . ? P1 P1 P2 85.40(8) 3 . ? C7 P1 P2 48.42(17) 3 . ? C7 P1 P2 49.22(17) . . ? Cl1 P1 P2 150.63(14) . . ? P2' P1 P2' 99.4(2) . 3 ? P1 P1 P2' 23.42(8) 3 3 ? C7 P1 P2' 46.50(16) 3 3 ? C7 P1 P2' 46.78(17) . 3 ? Cl1 P1 P2' 88.62(11) . 3 ? P2 P1 P2' 62.01(10) . 3 ? P2 P2 P2' 120.82(12) 3 . ? P2 P2 C1 175.5(2) 3 . ? P2' P2 C1 62.7(2) . . ? P2 P2 C7 70.5(2) 3 3 ? P2' P2 C7 64.40(18) . 3 ? C1 P2 C7 114.1(2) . 3 ? P2 P2 C7 68.21(19) 3 . ? P2' P2 C7 63.43(17) . . ? C1 P2 C7 112.7(2) . . ? C7 P2 C7 72.8(3) 3 . ? P2 P2 P1 94.60(8) 3 . ? P2' P2 P1 26.31(11) . . ? C1 P2 P1 88.97(19) . . ? C7 P2 P1 45.70(16) 3 . ? C7 P2 P1 46.60(16) . . ? P2 P2 P2' 33.45(7) 3 3 ? P2' P2 P2' 87.46(16) . 3 ? C1 P2 P2' 150.1(2) . 3 ? C7 P2 P2' 46.02(15) 3 3 ? C7 P2 P2' 46.26(16) . 3 ? P1 P2 P2' 61.18(10) . 3 ? P1 P2' P2 116.3(2) . . ? P1 P2' C1 177.8(3) . . ? P2 P2' C1 62.30(19) . . ? P1 P2' C7 67.5(2) . . ? P2 P2' C7 63.68(19) . . ? C1 P2' C7 112.6(3) . . ? P1 P2' C7 65.6(2) . 3 ? P2 P2' C7 62.42(19) . 3 ? C1 P2' C7 112.2(3) . 3 ? C7 P2' C7 72.2(2) . 3 ? P1 P2' P1 33.90(15) . 3 ? P2 P2' P1 82.51(14) . 3 ? C1 P2' P1 144.8(2) . 3 ? C7 P2' P1 43.26(16) . 3 ? C7 P2' P1 44.22(17) 3 3 ? P1 P2' P2 90.66(19) . 3 ? P2 P2' P2 25.74(11) . 3 ? C1 P2' P2 88.00(19) . 3 ? C7 P2' P2 45.28(16) . 3 ? C7 P2' P2 46.11(17) 3 3 ? P1 P2' P2 56.80(9) 3 3 ? C2A C1 C6 114.5(6) . . ? C2A C1 C2 30.4(6) . . ? C6 C1 C2 113.6(7) . . ? C2A C1 P2 122.3(7) . . ? C6 C1 P2 121.7(4) . . ? C2 C1 P2 108.7(8) . . ? C2A C1 P2' 112.4(8) . . ? C6 C1 P2' 113.9(4) . . ? C2 C1 P2' 130.2(8) . . ? P2 C1 P2' 55.03(17) . . ? C3 C2 C1 118.5(13) . . ? C1 C2A C3 117.4(10) . . ? C2 C3 C4 119.0(8) . . ? C2 C3 C2A 31.1(7) . . ? C4 C3 C2A 117.0(7) . . ? C3 C4 C5A 115.1(7) . . ? C3 C4 C5 114.5(7) . . ? C5A C4 C5 27.3(6) . . ? C6 C5 C4 118.5(11) . . ? C6 C5A C4 116.8(12) . . ? C5 C6 C5A 28.5(6) . . ? C5 C6 C1 120.1(8) . . ? C5A C6 C1 120.1(8) . . ? C8 C7 P1 125.1(4) . 3 ? C8 C7 P1 125.9(4) . . ? P1 C7 P1 57.3(2) 3 . ? C8 C7 P2 129.1(4) . 3 ? P1 C7 P2 85.9(2) 3 3 ? P1 C7 P2 104.5(2) . 3 ? C8 C7 P2' 125.3(3) . . ? P1 C7 P2' 90.2(2) 3 . ? P1 C7 P2' 38.70(15) . . ? P2 C7 P2' 88.7(2) 3 . ? C8 C7 P2 129.9(4) . . ? P1 C7 P2 104.6(3) 3 . ? P1 C7 P2 84.2(2) . . ? P2 C7 P2 41.34(18) 3 . ? P2' C7 P2 52.90(17) . . ? C8 C7 P2' 126.4(4) . 3 ? P1 C7 P2' 38.86(15) 3 3 ? P1 C7 P2' 89.0(2) . 3 ? P2 C7 P2' 53.17(16) 3 3 ? P2' C7 P2' 107.6(2) . 3 ? P2 C7 P2' 87.6(2) . 3 ? C7 C8 C9 111.5(4) . . ? C7 C8 C10 110.1(4) . . ? C9 C8 C10 108.6(4) . . ? C7 C8 C11 109.0(4) . . ? C9 C8 C11 109.8(4) . . ? C10 C8 C11 107.9(4) . . ? 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 P1 Cl1 P1 P2' -162.7(17) 3 . . . ? P1 Cl1 P1 C7 42.36(19) 3 . . 3 ? P1 Cl1 P1 C7 -40.99(18) 3 . . . ? P1 Cl1 P1 P2 0.17(15) 3 . . . ? P1 Cl1 P1 P2' 1.17(12) 3 . . 3 ? P2' P1 P2 P2 175.5(4) . . . 3 ? P1 P1 P2 P2 -0.3(3) 3 . . 3 ? C7 P1 P2 P2 -56.8(3) 3 . . 3 ? C7 P1 P2 P2 53.9(3) . . . 3 ? Cl1 P1 P2 P2 -0.5(4) . . . 3 ? P2' P1 P2 P2 -1.6(2) 3 . . 3 ? P1 P1 P2 P2' -175.8(4) 3 . . . ? C7 P1 P2 P2' 127.7(3) 3 . . . ? C7 P1 P2 P2' -121.6(3) . . . . ? Cl1 P1 P2 P2' -176.0(4) . . . . ? P2' P1 P2 P2' -177.1(2) 3 . . . ? P2' P1 P2 C1 -1.7(3) . . . . ? P1 P1 P2 C1 -177.5(2) 3 . . . ? C7 P1 P2 C1 126.0(3) 3 . . . ? C7 P1 P2 C1 -123.3(3) . . . . ? Cl1 P1 P2 C1 -177.7(3) . . . . ? P2' P1 P2 C1 -178.8(2) 3 . . . ? P2' P1 P2 C7 -127.7(3) . . . 3 ? P1 P1 P2 C7 56.5(3) 3 . . 3 ? C7 P1 P2 C7 110.7(2) . . . 3 ? Cl1 P1 P2 C7 56.3(3) . . . 3 ? P2' P1 P2 C7 55.2(2) 3 . . 3 ? P2' P1 P2 C7 121.6(3) . . . . ? P1 P1 P2 C7 -54.3(2) 3 . . . ? C7 P1 P2 C7 -110.7(2) 3 . . . ? Cl1 P1 P2 C7 -54.4(3) . . . . ? P2' P1 P2 C7 -55.5(2) 3 . . . ? P2' P1 P2 P2' 177.1(2) . . . 3 ? P1 P1 P2 P2' 1.28(15) 3 . . 3 ? C7 P1 P2 P2' -55.2(2) 3 . . 3 ? C7 P1 P2 P2' 55.5(2) . . . 3 ? Cl1 P1 P2 P2' 1.1(3) . . . 3 ? P1 P1 P2' P2 5.0(4) 3 . . . ? C7 P1 P2' P2 -37.7(2) 3 . . . ? C7 P1 P2' P2 42.2(2) . . . . ? Cl1 P1 P2' P2 166.2(15) . . . . ? P2' P1 P2' P2 2.6(2) 3 . . . ? P1 P1 P2' C1 56(8) 3 . . . ? C7 P1 P2' C1 13(7) 3 . . . ? C7 P1 P2' C1 93(8) . . . . ? Cl1 P1 P2' C1 -143(7) . . . . ? P2 P1 P2' C1 51(7) . . . . ? P2' P1 P2' C1 53(7) 3 . . . ? P1 P1 P2' C7 -37.3(3) 3 . . . ? C7 P1 P2' C7 -79.9(3) 3 . . . ? Cl1 P1 P2' C7 124.0(16) . . . . ? P2 P1 P2' C7 -42.2(2) . . . . ? P2' P1 P2' C7 -39.61(16) 3 . . . ? P1 P1 P2' C7 42.6(3) 3 . . 3 ? C7 P1 P2' C7 79.9(3) . . . 3 ? Cl1 P1 P2' C7 -156.1(16) . . . 3 ? P2 P1 P2' C7 37.7(2) . . . 3 ? P2' P1 P2' C7 40.28(16) 3 . . 3 ? C7 P1 P2' P1 -42.6(3) 3 . . 3 ? C7 P1 P2' P1 37.3(3) . . . 3 ? Cl1 P1 P2' P1 161.3(19) . . . 3 ? P2 P1 P2' P1 -5.0(4) . . . 3 ? P2' P1 P2' P1 -2.4(2) 3 . . 3 ? P1 P1 P2' P2 2.7(3) 3 . . 3 ? C7 P1 P2' P2 -39.95(17) 3 . . 3 ? C7 P1 P2' P2 39.94(17) . . . 3 ? Cl1 P1 P2' P2 163.9(16) . . . 3 ? P2 P1 P2' P2 -2.27(19) . . . 3 ? P2' P1 P2' P2 0.33(10) 3 . . 3 ? P2 P2 P2' P1 -5.2(4) 3 . . . ? C1 P2 P2' P1 178.0(3) . . . . ? C7 P2 P2' P1 38.9(3) 3 . . . ? C7 P2 P2' P1 -43.8(3) . . . . ? P2' P2 P2' P1 -2.5(2) 3 . . . ? P2 P2 P2' C1 176.7(4) 3 . . . ? C7 P2 P2' C1 -139.1(3) 3 . . . ? C7 P2 P2' C1 138.1(3) . . . . ? P1 P2 P2' C1 -178.0(3) . . . . ? P2' P2 P2' C1 179.4(2) 3 . . . ? P2 P2 P2' C7 38.6(3) 3 . . . ? C1 P2 P2' C7 -138.1(3) . . . . ? C7 P2 P2' C7 82.7(3) 3 . . . ? P1 P2 P2' C7 43.8(3) . . . . ? P2' P2 P2' C7 41.27(16) 3 . . . ? P2 P2 P2' C7 -44.1(3) 3 . . 3 ? C1 P2 P2' C7 139.1(3) . . . 3 ? C7 P2 P2' C7 -82.7(3) . . . 3 ? P1 P2 P2' C7 -38.9(3) . . . 3 ? P2' P2 P2' C7 -41.45(16) 3 . . 3 ? P2 P2 P2' P1 -2.4(3) 3 . . 3 ? C1 P2 P2' P1 -179.2(2) . . . 3 ? C7 P2 P2' P1 41.69(18) 3 . . 3 ? C7 P2 P2' P1 -41.03(17) . . . 3 ? P1 P2 P2' P1 2.8(2) . . . 3 ? P2' P2 P2' P1 0.24(7) 3 . . 3 ? C1 P2 P2' P2 -176.7(4) . . . 3 ? C7 P2 P2' P2 44.1(3) 3 . . 3 ? C7 P2 P2' P2 -38.6(3) . . . 3 ? P1 P2 P2' P2 5.2(4) . . . 3 ? P2' P2 P2' P2 2.7(3) 3 . . 3 ? P2 P2 C1 C2A -45(4) 3 . . . ? P2' P2 C1 C2A 96.2(12) . . . . ? C7 P2 C1 C2A 136.4(11) 3 . . . ? C7 P2 C1 C2A 55.8(12) . . . . ? P1 P2 C1 C2A 97.0(12) . . . . ? P2' P2 C1 C2A 95.0(12) 3 . . . ? P2 P2 C1 C6 120(3) 3 . . . ? P2' P2 C1 C6 -98.6(5) . . . . ? C7 P2 C1 C6 -58.4(6) 3 . . . ? C7 P2 C1 C6 -139.0(5) . . . . ? P1 P2 C1 C6 -97.8(5) . . . . ? P2' P2 C1 C6 -99.8(6) 3 . . . ? P2 P2 C1 C2 -15(4) 3 . . . ? P2' P2 C1 C2 126.4(12) . . . . ? C7 P2 C1 C2 166.7(11) 3 . . . ? C7 P2 C1 C2 86.1(12) . . . . ? P1 P2 C1 C2 127.3(11) . . . . ? P2' P2 C1 C2 125.2(12) 3 . . . ? P2 P2 C1 P2' -141(4) 3 . . . ? C7 P2 C1 P2' 40.2(3) 3 . . . ? C7 P2 C1 P2' -40.3(2) . . . . ? P1 P2 C1 P2' 0.86(14) . . . . ? P2' P2 C1 P2' -1.2(4) 3 . . . ? P1 P2' C1 C2A -166(7) . . . . ? P2 P2' C1 C2A -114.7(10) . . . . ? C7 P2' C1 C2A -74.3(10) . . . . ? C7 P2' C1 C2A -153.5(10) 3 . . . ? P1 P2' C1 C2A -113.3(10) 3 . . . ? P2 P2' C1 C2A -113.3(10) 3 . . . ? P1 P2' C1 C6 61(8) . . . . ? P2 P2' C1 C6 113.0(5) . . . . ? C7 P2' C1 C6 153.4(4) . . . . ? C7 P2' C1 C6 74.2(5) 3 . . . ? P1 P2' C1 C6 114.4(5) 3 . . . ? P2 P2' C1 C6 114.4(5) 3 . . . ? P1 P2' C1 C2 -137(7) . . . . ? P2 P2' C1 C2 -85.6(14) . . . . ? C7 P2' C1 C2 -45.2(14) . . . . ? C7 P2' C1 C2 -124.3(14) 3 . . . ? P1 P2' C1 C2 -84.1(14) 3 . . . ? P2 P2' C1 C2 -84.1(14) 3 . . . ? P1 P2' C1 P2 -52(7) . . . . ? C7 P2' C1 P2 40.4(2) . . . . ? C7 P2' C1 P2 -38.8(2) 3 . . . ? P1 P2' C1 P2 1.4(4) 3 . . . ? P2 P2' C1 P2 1.42(16) 3 . . . ? C2A C1 C2 C3 -66(2) . . . . ? C6 C1 C2 C3 32(2) . . . . ? P2 C1 C2 C3 171.0(16) . . . . ? P2' C1 C2 C3 -129.3(13) . . . . ? C6 C1 C2A C3 -36(2) . . . . ? C2 C1 C2A C3 59.1(18) . . . . ? P2 C1 C2A C3 130.0(11) . . . . ? P2' C1 C2A C3 -168.3(12) . . . . ? C1 C2 C3 C4 -34(3) . . . . ? C1 C2 C3 C2A 61.2(19) . . . . ? C1 C2A C3 C2 -64.8(18) . . . . ? C1 C2A C3 C4 37(2) . . . . ? C2 C3 C4 C5A 1(2) . . . . ? C2A C3 C4 C5A -34.2(18) . . . . ? C2 C3 C4 C5 31(2) . . . . ? C2A C3 C4 C5 -4.1(17) . . . . ? C3 C4 C5 C6 -30(2) . . . . ? C5A C4 C5 C6 68(2) . . . . ? C3 C4 C5A C6 32(2) . . . . ? C5 C4 C5A C6 -63(2) . . . . ? C4 C5 C6 C5A -67(2) . . . . ? C4 C5 C6 C1 32(3) . . . . ? C4 C5A C6 C5 65(2) . . . . ? C4 C5A C6 C1 -33(3) . . . . ? C2A C1 C6 C5 1.9(18) . . . . ? C2 C1 C6 C5 -31.4(19) . . . . ? P2 C1 C6 C5 -164.4(13) . . . . ? P2' C1 C6 C5 133.2(13) . . . . ? C2A C1 C6 C5A 35.0(19) . . . . ? C2 C1 C6 C5A 1.7(19) . . . . ? P2 C1 C6 C5A -131.3(14) . . . . ? P2' C1 C6 C5A 166.3(14) . . . . ? P2' P1 C7 C8 103.7(4) . . . . ? P1 P1 C7 C8 -112.2(5) 3 . . . ? C7 P1 C7 C8 -177.8(5) 3 . . . ? Cl1 P1 C7 C8 -69.0(5) . . . . ? P2 P1 C7 C8 136.3(5) . . . . ? P2' P1 C7 C8 -136.0(5) 3 . . . ? P2' P1 C7 P1 -144.1(3) . . . 3 ? C7 P1 C7 P1 -65.6(3) 3 . . 3 ? Cl1 P1 C7 P1 43.21(16) . . . 3 ? P2 P1 C7 P1 -111.6(2) . . . 3 ? P2' P1 C7 P1 -23.84(16) 3 . . 3 ? P2' P1 C7 P2 -68.9(3) . . . 3 ? P1 P1 C7 P2 75.2(2) 3 . . 3 ? C7 P1 C7 P2 9.7(2) 3 . . 3 ? Cl1 P1 C7 P2 118.5(2) . . . 3 ? P2 P1 C7 P2 -36.31(19) . . . 3 ? P2' P1 C7 P2 51.41(18) 3 . . 3 ? P1 P1 C7 P2' 144.1(3) 3 . . . ? C7 P1 C7 P2' 78.6(2) 3 . . . ? Cl1 P1 C7 P2' -172.6(2) . . . . ? P2 P1 C7 P2' 32.6(2) . . . . ? P2' P1 C7 P2' 120.3(3) 3 . . . ? P2' P1 C7 P2 -32.6(2) . . . . ? P1 P1 C7 P2 111.6(2) 3 . . . ? C7 P1 C7 P2 46.00(15) 3 . . . ? Cl1 P1 C7 P2 154.77(16) . . . . ? P2' P1 C7 P2 87.7(2) 3 . . . ? P2' P1 C7 P2' -120.3(3) . . . 3 ? P1 P1 C7 P2' 23.84(16) 3 . . 3 ? C7 P1 C7 P2' -41.7(3) 3 . . 3 ? Cl1 P1 C7 P2' 67.0(2) . . . 3 ? P2 P1 C7 P2' -87.7(2) . . . 3 ? P1 P2' C7 C8 -105.5(5) . . . . ? P2 P2' C7 C8 116.8(5) . . . . ? C1 P2' C7 C8 77.0(5) . . . . ? C7 P2' C7 C8 -175.8(3) 3 . . . ? P1 P2' C7 C8 -135.0(5) 3 . . . ? P2 P2' C7 C8 139.2(5) 3 . . . ? P1 P2' C7 P1 29.5(2) . . . 3 ? P2 P2' C7 P1 -108.3(2) . . . 3 ? C1 P2' C7 P1 -148.1(2) . . . 3 ? C7 P2' C7 P1 -40.8(3) 3 . . 3 ? P2 P2' C7 P1 -85.9(2) 3 . . 3 ? P2 P2' C7 P1 -137.8(2) . . . . ? C1 P2' C7 P1 -177.6(3) . . . . ? C7 P2' C7 P1 -70.3(2) 3 . . . ? P1 P2' C7 P1 -29.5(2) 3 . . . ? P2 P2' C7 P1 -115.4(3) 3 . . . ? P1 P2' C7 P2 115.4(3) . . . 3 ? P2 P2' C7 P2 -22.40(18) . . . 3 ? C1 P2' C7 P2 -62.2(3) . . . 3 ? C7 P2' C7 P2 45.0(2) 3 . . 3 ? P1 P2' C7 P2 85.9(2) 3 . . 3 ? P1 P2' C7 P2 137.8(2) . . . . ? C1 P2' C7 P2 -39.8(2) . . . . ? C7 P2' C7 P2 67.45(18) 3 . . . ? P1 P2' C7 P2 108.3(2) 3 . . . ? P2 P2' C7 P2 22.40(18) 3 . . . ? P1 P2' C7 P2' 64.9(3) . . . 3 ? P2 P2' C7 P2' -72.9(3) . . . 3 ? C1 P2' C7 P2' -112.7(3) . . . 3 ? C7 P2' C7 P2' -5.5(4) 3 . . 3 ? P1 P2' C7 P2' 35.37(18) 3 . . 3 ? P2 P2' C7 P2' -50.5(2) 3 . . 3 ? P2 P2 C7 C8 107.1(5) 3 . . . ? P2' P2 C7 C8 -108.1(5) . . . . ? C1 P2 C7 C8 -68.1(5) . . . . ? C7 P2 C7 C8 -177.6(6) 3 . . . ? P1 P2 C7 C8 -133.1(5) . . . . ? P2' P2 C7 C8 137.6(5) 3 . . . ? P2 P2 C7 P1 -65.8(2) 3 . . 3 ? P2' P2 C7 P1 78.9(2) . . . 3 ? C1 P2 C7 P1 118.9(3) . . . 3 ? C7 P2 C7 P1 9.5(2) 3 . . 3 ? P1 P2 C7 P1 53.9(2) . . . 3 ? P2' P2 C7 P1 -35.29(16) 3 . . 3 ? P2 P2 C7 P1 -119.8(2) 3 . . . ? P2' P2 C7 P1 24.98(15) . . . . ? C1 P2 C7 P1 65.0(3) . . . . ? C7 P2 C7 P1 -44.48(14) 3 . . . ? P2' P2 C7 P1 -89.2(2) 3 . . . ? P2' P2 C7 P2 144.8(2) . . . 3 ? C1 P2 C7 P2 -175.2(3) . . . 3 ? C7 P2 C7 P2 75.3(3) 3 . . 3 ? P1 P2 C7 P2 119.8(2) . . . 3 ? P2' P2 C7 P2 30.6(2) 3 . . 3 ? P2 P2 C7 P2' -144.8(2) 3 . . . ? C1 P2 C7 P2' 40.0(2) . . . . ? C7 P2 C7 P2' -69.46(18) 3 . . . ? P1 P2 C7 P2' -24.98(15) . . . . ? P2' P2 C7 P2' -114.2(2) 3 . . . ? P2 P2 C7 P2' -30.6(2) 3 . . 3 ? P2' P2 C7 P2' 114.2(2) . . . 3 ? C1 P2 C7 P2' 154.2(2) . . . 3 ? C7 P2 C7 P2' 44.8(2) 3 . . 3 ? P1 P2 C7 P2' 89.2(2) . . . 3 ? P1 C7 C8 C9 139.9(4) 3 . . . ? P1 C7 C8 C9 -148.0(4) . . . . ? P2 C7 C8 C9 22.7(6) 3 . . . ? P2' C7 C8 C9 -99.9(5) . . . . ? P2 C7 C8 C9 -31.7(6) . . . . ? P2' C7 C8 C9 91.6(5) 3 . . . ? P1 C7 C8 C10 19.3(6) 3 . . . ? P1 C7 C8 C10 91.4(5) . . . . ? P2 C7 C8 C10 -97.9(5) 3 . . . ? P2' C7 C8 C10 139.5(4) . . . . ? P2 C7 C8 C10 -152.3(4) . . . . ? P2' C7 C8 C10 -29.0(6) 3 . . . ? P1 C7 C8 C11 -98.8(5) 3 . . . ? P1 C7 C8 C11 -26.7(6) . . . . ? P2 C7 C8 C11 144.0(4) 3 . . . ? P2' C7 C8 C11 21.4(6) . . . . ? P2 C7 C8 C11 89.6(5) . . . . ? P2' C7 C8 C11 -147.1(4) 3 . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.285 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.071