data_c05307 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H23 O6 P W' _chemical_formula_weight 514.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'W' 'W' -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 12.891(2) _cell_length_b 9.4512(17) _cell_length_c 15.714(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.093(3) _cell_angle_gamma 90.00 _cell_volume 1848.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.848 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 6.360 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 ? _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 10605 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3237 _reflns_number_gt 2811 _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^)+(0.0000P)^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 SHELXL _refine_ls_extinction_coef 0.00001(11) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3237 _refine_ls_number_parameters 216 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0615 _refine_ls_wR_factor_gt 0.0607 _refine_ls_goodness_of_fit_ref 2.108 _refine_ls_restrained_S_all 2.108 _refine_ls_shift/su_max 0.041 _refine_ls_shift/su_mean 0.004 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 0.21175(2) 0.87229(3) 0.373890(16) 0.01386(11) Uani 1 1 d . . . P1 P 0.18929(14) 0.83864(18) 0.21252(10) 0.0147(4) Uani 1 1 d . . . C1 C 0.0619(6) 0.8209(7) 0.3189(4) 0.0178(16) Uani 1 1 d . . . O2 O -0.0262(4) 0.7787(5) 0.2898(3) 0.0249(12) Uani 1 1 d . . . C3 C 0.1876(5) 0.6887(7) 0.4233(4) 0.0096(14) Uani 1 1 d . . . O4 O 0.1669(4) 0.5827(5) 0.4494(3) 0.0250(12) Uani 1 1 d . . . C5 C 0.1687(5) 0.6581(7) 0.1724(4) 0.0212(16) Uani 1 1 d . . . H5A H 0.0993 0.6259 0.1760 0.032 Uiso 1 1 calc R . . H5B H 0.2233 0.5983 0.2079 0.032 Uiso 1 1 calc R . . H5C H 0.1724 0.6547 0.1123 0.032 Uiso 1 1 calc R . . C6 C 0.0812(5) 0.9400(7) 0.1427(4) 0.0208(16) Uani 1 1 d . . . H6A H 0.0846 0.9326 0.0826 0.031 Uiso 1 1 calc R . . H6B H 0.0881 1.0374 0.1606 0.031 Uiso 1 1 calc R . . H6C H 0.0135 0.9038 0.1479 0.031 Uiso 1 1 calc R . . C7 C 0.3045(5) 0.8984(8) 0.1760(4) 0.0247(17) Uani 1 1 d . . . H7A H 0.2930 0.8785 0.1144 0.037 Uiso 1 1 calc R . . H7B H 0.3678 0.8498 0.2087 0.037 Uiso 1 1 calc R . . H7C H 0.3137 0.9984 0.1858 0.037 Uiso 1 1 calc R . . O8 O 0.3545(3) 0.7729(5) 0.3575(3) 0.0163(10) Uani 1 1 d . . . C9 C 0.4401(5) 0.7418(7) 0.4172(4) 0.0191(16) Uani 1 1 d . . . C10 C 0.4660(6) 0.7883(8) 0.5044(4) 0.0238(17) Uani 1 1 d . . . H10 H 0.5268 0.7500 0.5430 0.029 Uiso 1 1 calc R . . C11 C 0.4075(5) 0.8875(7) 0.5376(4) 0.0173(15) Uani 1 1 d . . . O12 O 0.3156(3) 0.9339(4) 0.4966(3) 0.0169(10) Uani 1 1 d . . . C13 C 0.5178(6) 0.6481(8) 0.3870(4) 0.0287(18) Uani 1 1 d . . . H13A H 0.4885 0.5545 0.3763 0.043 Uiso 1 1 calc R . . H13B H 0.5846 0.6446 0.4318 0.043 Uiso 1 1 calc R . . H13C H 0.5301 0.6855 0.3336 0.043 Uiso 1 1 calc R . . C14 C 0.4509(5) 0.9452(8) 0.6303(4) 0.0230(17) Uani 1 1 d . . . H14A H 0.4165 1.0337 0.6357 0.034 Uiso 1 1 calc R . . H14B H 0.5270 0.9595 0.6418 0.034 Uiso 1 1 calc R . . H14C H 0.4365 0.8789 0.6721 0.034 Uiso 1 1 calc R . . O15 O 0.1213(3) 1.0086(5) 0.4355(3) 0.0170(10) Uani 1 1 d . . . C16 C 0.1385(5) 1.1372(8) 0.4543(4) 0.0170(15) Uani 1 1 d . . . C17 C 0.1958(5) 1.2322(7) 0.4167(4) 0.0154(15) Uani 1 1 d . . . H17 H 0.1982 1.3261 0.4349 0.018 Uiso 1 1 calc R . . C18 C 0.2498(5) 1.1970(8) 0.3540(4) 0.0197(17) Uani 1 1 d . . . O19 O 0.2674(4) 1.0708(5) 0.3303(3) 0.0192(11) Uani 1 1 d . . . C20 C 0.0860(6) 1.1922(7) 0.5238(4) 0.0227(17) Uani 1 1 d . . . H20A H 0.0152 1.1528 0.5138 0.034 Uiso 1 1 calc R . . H20B H 0.0812 1.2935 0.5202 0.034 Uiso 1 1 calc R . . H20C H 0.1283 1.1650 0.5812 0.034 Uiso 1 1 calc R . . C21 C 0.2917(6) 1.3138(7) 0.3053(4) 0.0236(17) Uani 1 1 d . . . H21A H 0.3612 1.2879 0.2987 0.035 Uiso 1 1 calc R . . H21B H 0.2974 1.4002 0.3383 0.035 Uiso 1 1 calc R . . H21C H 0.2430 1.3270 0.2482 0.035 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 W1 0.01817(17) 0.00938(15) 0.01528(14) -0.00049(13) 0.00657(9) 0.00060(14) P1 0.0192(10) 0.0100(10) 0.0160(8) 0.0010(7) 0.0066(7) 0.0022(7) C1 0.034(5) 0.015(4) 0.010(3) 0.005(3) 0.015(3) 0.004(3) O2 0.021(3) 0.033(3) 0.022(3) 0.002(2) 0.009(2) -0.006(2) C3 0.014(4) 0.006(4) 0.008(3) -0.006(3) 0.002(3) 0.002(3) O4 0.040(3) 0.018(3) 0.016(2) -0.002(2) 0.007(2) 0.007(2) C5 0.027(4) 0.012(4) 0.024(4) -0.002(3) 0.006(3) 0.005(3) C6 0.025(4) 0.015(4) 0.025(4) 0.001(3) 0.011(3) 0.006(3) C7 0.033(4) 0.024(5) 0.020(4) -0.002(3) 0.011(3) 0.000(3) O8 0.014(3) 0.017(3) 0.018(2) -0.001(2) 0.005(2) 0.004(2) C9 0.018(4) 0.013(4) 0.027(4) 0.001(3) 0.008(3) 0.000(3) C10 0.024(4) 0.025(4) 0.021(4) 0.001(3) 0.003(3) 0.004(3) C11 0.022(4) 0.014(4) 0.017(3) 0.000(3) 0.008(3) -0.007(3) O12 0.017(3) 0.012(3) 0.021(2) -0.002(2) 0.004(2) 0.000(2) C13 0.029(4) 0.032(5) 0.026(4) -0.001(4) 0.008(3) 0.009(4) C14 0.025(4) 0.024(4) 0.021(4) -0.002(3) 0.007(3) -0.007(3) O15 0.021(3) 0.011(3) 0.021(2) -0.002(2) 0.010(2) 0.002(2) C16 0.018(4) 0.011(4) 0.019(3) -0.002(3) -0.002(3) 0.002(3) C17 0.021(4) 0.006(4) 0.019(4) -0.006(3) 0.005(3) 0.000(3) C18 0.015(4) 0.015(4) 0.022(4) 0.006(3) -0.007(3) -0.002(3) O19 0.023(3) 0.009(3) 0.028(3) -0.002(2) 0.011(2) -0.001(2) C20 0.031(4) 0.018(4) 0.019(4) -0.003(3) 0.008(3) 0.001(3) C21 0.029(4) 0.015(4) 0.027(4) 0.009(3) 0.008(3) -0.007(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 W1 C3 1.958(7) . ? W1 C1 1.961(8) . ? W1 O12 2.122(4) . ? W1 O15 2.131(4) . ? W1 O8 2.141(4) . ? W1 O19 2.182(4) . ? W1 P1 2.4966(16) . ? P1 C6 1.807(6) . ? P1 C5 1.814(7) . ? P1 C7 1.816(7) . ? C1 O2 1.177(8) . ? C3 O4 1.141(7) . ? O8 C9 1.282(7) . ? C9 C10 1.394(9) . ? C9 C13 1.503(9) . ? C10 C11 1.388(9) . ? C11 O12 1.269(7) . ? C11 C14 1.520(8) . ? O15 C16 1.257(8) . ? C16 C17 1.389(9) . ? C16 C20 1.519(9) . ? C17 C18 1.387(9) . ? C18 O19 1.287(8) . ? C18 C21 1.520(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 C3 W1 C1 73.5(3) . . ? C3 W1 O12 90.6(2) . . ? C1 W1 O12 141.7(2) . . ? C3 W1 O15 101.2(2) . . ? C1 W1 O15 76.0(2) . . ? O12 W1 O15 73.26(16) . . ? C3 W1 O8 83.6(2) . . ? C1 W1 O8 128.1(2) . . ? O12 W1 O8 82.57(16) . . ? O15 W1 O8 155.33(16) . . ? C3 W1 O19 170.2(2) . . ? C1 W1 O19 116.2(2) . . ? O12 W1 O19 82.43(16) . . ? O15 W1 O19 83.48(17) . . ? O8 W1 O19 88.66(17) . . ? C3 W1 P1 107.52(17) . . ? C1 W1 P1 71.34(17) . . ? O12 W1 P1 146.77(12) . . ? O15 W1 P1 127.29(12) . . ? O8 W1 P1 72.43(11) . . ? O19 W1 P1 75.59(12) . . ? C6 P1 C5 105.5(3) . . ? C6 P1 C7 102.0(3) . . ? C5 P1 C7 103.9(3) . . ? C6 P1 W1 114.6(2) . . ? C5 P1 W1 116.1(2) . . ? C7 P1 W1 113.1(2) . . ? O2 C1 W1 174.0(6) . . ? O4 C3 W1 175.7(6) . . ? C9 O8 W1 128.0(4) . . ? O8 C9 C10 125.9(6) . . ? O8 C9 C13 115.0(6) . . ? C10 C9 C13 119.1(6) . . ? C11 C10 C9 124.6(6) . . ? O12 C11 C10 124.7(6) . . ? O12 C11 C14 115.1(6) . . ? C10 C11 C14 120.2(6) . . ? C11 O12 W1 130.6(4) . . ? C16 O15 W1 127.4(4) . . ? O15 C16 C17 127.3(6) . . ? O15 C16 C20 114.6(6) . . ? C17 C16 C20 118.1(6) . . ? C16 C17 C18 124.6(6) . . ? O19 C18 C17 125.9(6) . . ? O19 C18 C21 114.5(6) . . ? C17 C18 C21 119.5(6) . . ? C18 O19 W1 127.5(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 C3 W1 P1 C6 118.1(3) . . . . ? C1 W1 P1 C6 53.0(3) . . . . ? O12 W1 P1 C6 -121.7(3) . . . . ? O15 W1 P1 C6 -1.6(3) . . . . ? O8 W1 P1 C6 -164.8(3) . . . . ? O19 W1 P1 C6 -71.6(3) . . . . ? C3 W1 P1 C5 -5.4(3) . . . . ? C1 W1 P1 C5 -70.5(3) . . . . ? O12 W1 P1 C5 114.7(3) . . . . ? O15 W1 P1 C5 -125.1(3) . . . . ? O8 W1 P1 C5 71.7(3) . . . . ? O19 W1 P1 C5 164.9(3) . . . . ? C3 W1 P1 C7 -125.5(3) . . . . ? C1 W1 P1 C7 169.4(3) . . . . ? O12 W1 P1 C7 -5.3(4) . . . . ? O15 W1 P1 C7 114.8(3) . . . . ? O8 W1 P1 C7 -48.4(3) . . . . ? O19 W1 P1 C7 44.8(3) . . . . ? C3 W1 C1 O2 -4(5) . . . . ? O12 W1 C1 O2 -73(5) . . . . ? O15 W1 C1 O2 -111(5) . . . . ? O8 W1 C1 O2 63(5) . . . . ? O19 W1 C1 O2 174(5) . . . . ? P1 W1 C1 O2 111(5) . . . . ? C1 W1 C3 O4 -8(7) . . . . ? O12 W1 C3 O4 137(7) . . . . ? O15 W1 C3 O4 64(7) . . . . ? O8 W1 C3 O4 -141(7) . . . . ? O19 W1 C3 O4 -179(100) . . . . ? P1 W1 C3 O4 -72(7) . . . . ? C3 W1 O8 C9 -73.0(6) . . . . ? C1 W1 O8 C9 -136.1(5) . . . . ? O12 W1 O8 C9 18.5(5) . . . . ? O15 W1 O8 C9 29.9(8) . . . . ? O19 W1 O8 C9 101.0(5) . . . . ? P1 W1 O8 C9 176.3(6) . . . . ? W1 O8 C9 C10 -11.9(10) . . . . ? W1 O8 C9 C13 169.0(4) . . . . ? O8 C9 C10 C11 -6.9(12) . . . . ? C13 C9 C10 C11 172.2(7) . . . . ? C9 C10 C11 O12 10.3(11) . . . . ? C9 C10 C11 C14 -171.8(6) . . . . ? C10 C11 O12 W1 6.0(10) . . . . ? C14 C11 O12 W1 -172.0(4) . . . . ? C3 W1 O12 C11 67.5(6) . . . . ? C1 W1 O12 C11 131.1(6) . . . . ? O15 W1 O12 C11 169.0(6) . . . . ? O8 W1 O12 C11 -16.0(5) . . . . ? O19 W1 O12 C11 -105.6(5) . . . . ? P1 W1 O12 C11 -57.0(6) . . . . ? C3 W1 O15 C16 151.2(5) . . . . ? C1 W1 O15 C16 -139.2(5) . . . . ? O12 W1 O15 C16 63.9(5) . . . . ? O8 W1 O15 C16 52.1(7) . . . . ? O19 W1 O15 C16 -20.1(5) . . . . ? P1 W1 O15 C16 -86.4(5) . . . . ? W1 O15 C16 C17 22.1(9) . . . . ? W1 O15 C16 C20 -160.2(4) . . . . ? O15 C16 C17 C18 -3.8(11) . . . . ? C20 C16 C17 C18 178.6(6) . . . . ? C16 C17 C18 O19 -10.1(11) . . . . ? C16 C17 C18 C21 168.5(6) . . . . ? C17 C18 O19 W1 3.8(10) . . . . ? C21 C18 O19 W1 -174.9(4) . . . . ? C3 W1 O19 C18 -111.0(12) . . . . ? C1 W1 O19 C18 78.8(6) . . . . ? O12 W1 O19 C18 -66.0(5) . . . . ? O15 W1 O19 C18 7.9(5) . . . . ? O8 W1 O19 C18 -148.7(5) . . . . ? P1 W1 O19 C18 139.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.805 _refine_diff_density_min -1.309 _refine_diff_density_rms 0.162