# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Li-Min Zheng' _publ_contact_author_email lmzheng@netra.nju.edu.cn _publ_author_name 'Li-Min Zheng' data_110427am _database_code_depnum_ccdc_archive 'CCDC 873704' #TrackingRef '- compound 1-r.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H22 O20 P2 V3' _chemical_formula_weight 725.08 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' V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall 'p 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.5302(10) _cell_length_b 9.0426(9) _cell_length_c 14.3609(15) _cell_angle_alpha 90.00 _cell_angle_beta 95.873(2) _cell_angle_gamma 90.00 _cell_volume 1231.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 3661 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 25.00 _exptl_crystal_description sheet _exptl_crystal_colour blue _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.956 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 730 _exptl_absorpt_coefficient_mu 1.339 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.765 _exptl_absorpt_correction_T_max 0.875 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6026 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0270 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3661 _reflns_number_gt 3522 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; 'Hirshfeld Rigid-bond Test reveals large DELU values for bonds involving the V atoms, hence it is necessary to use the DELU instruction for V1, O9 and O11, V2 and O4W. Now there are 5 Uiso/Uij restrained atom sites and 5 least-squares restraints used in the refinement.' 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^)+(0.1050P)^2^+0.3380P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(3) _chemical_absolute_configuration rm _refine_ls_number_reflns 3661 _refine_ls_number_parameters 352 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1268 _refine_ls_wR_factor_gt 0.1251 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 V1 V 0.60358(8) 0.79899(9) 0.73746(6) 0.0222(2) Uani 1 1 d U . . V2 V 0.29135(9) 0.65646(11) 1.00563(6) 0.0260(2) Uani 1 1 d U . . V3 V 1.10839(8) 1.08850(9) 0.75910(7) 0.0240(2) Uani 1 1 d . . . P1 P 0.78076(13) 1.10621(15) 0.78038(9) 0.0205(3) Uani 1 1 d . . . P2 P 0.28812(13) 0.77682(14) 0.78340(9) 0.0212(3) Uani 1 1 d . . . C1 C 0.7671(5) 1.2452(6) 0.6922(3) 0.0217(11) Uani 1 1 d . . . C2 C 0.6658(6) 1.2303(8) 0.6158(4) 0.0332(13) Uani 1 1 d . . . H2 H 0.6077 1.1475 0.6109 0.040 Uiso 1 1 calc R . . C3 C 0.6514(7) 1.3376(8) 0.5475(4) 0.0429(17) Uani 1 1 d . . . H3 H 0.5825 1.3262 0.4973 0.051 Uiso 1 1 calc R . . C4 C 0.7335(8) 1.4575(8) 0.5514(4) 0.0447(17) Uani 1 1 d . . . H4 H 0.7234 1.5270 0.5034 0.054 Uiso 1 1 calc R . . C5 C 0.8363(6) 1.4785(7) 0.6291(4) 0.0304(12) Uani 1 1 d . . . H5 H 0.8903 1.5643 0.6343 0.036 Uiso 1 1 calc R . . C6 C 0.8547(5) 1.3712(6) 0.6960(4) 0.0230(11) Uani 1 1 d . . . C7 C 0.9687(6) 1.3968(7) 0.7765(4) 0.0256(12) Uani 1 1 d . . . C8 C 0.2670(5) 0.6477(6) 0.6885(3) 0.0201(10) Uani 1 1 d . . . C9 C 0.1650(5) 0.6662(7) 0.6154(4) 0.0309(12) Uani 1 1 d . . . H9 H 0.1078 0.7496 0.6141 0.037 Uiso 1 1 calc R . . C10 C 0.1439(7) 0.5638(9) 0.5428(4) 0.0452(18) Uani 1 1 d . . . H10 H 0.0775 0.5801 0.4917 0.054 Uiso 1 1 calc R . . C11 C 0.2269(7) 0.4352(9) 0.5497(4) 0.0453(18) Uani 1 1 d . . . H11 H 0.2126 0.3624 0.5040 0.054 Uiso 1 1 calc R . . C12 C 0.3266(7) 0.4163(7) 0.6217(4) 0.0373(14) Uani 1 1 d . . . H12 H 0.3792 0.3295 0.6256 0.045 Uiso 1 1 calc R . . C13 C 0.3530(5) 0.5233(6) 0.6906(3) 0.0219(11) Uani 1 1 d . . . C14 C 0.4712(6) 0.5004(6) 0.7666(4) 0.0259(12) Uani 1 1 d . . . O1 O 0.6556(4) 1.0059(4) 0.7629(3) 0.0309(9) Uani 1 1 d . . . O2 O 0.9157(4) 1.0171(4) 0.7719(3) 0.0283(9) Uani 1 1 d . . . O3 O 0.7856(4) 1.1820(5) 0.8742(2) 0.0327(9) Uani 1 1 d . . . O4 O 0.4216(4) 0.8666(5) 0.7737(3) 0.0328(9) Uani 1 1 d . . . O5 O 0.3039(4) 0.6852(5) 0.8710(2) 0.0329(9) Uani 1 1 d . . . O6 O 0.1600(4) 0.8781(5) 0.7775(3) 0.0319(9) Uani 1 1 d . . . O7 O 0.9748(4) 1.5162(5) 0.8157(3) 0.0362(10) Uani 1 1 d . . . O8 O 1.0578(4) 1.2930(4) 0.7982(3) 0.0279(8) Uani 1 1 d . . . O9 O 0.5619(4) 0.5989(4) 0.7860(3) 0.0286(8) Uani 1 1 d U . . O10 O 0.4779(4) 0.3767(5) 0.8098(3) 0.0356(10) Uani 1 1 d . . . O11 O 0.5918(5) 0.7797(5) 0.6283(3) 0.0417(10) Uani 1 1 d U . . O12 O 0.4311(4) 0.5662(5) 1.0332(3) 0.0397(10) Uani 1 1 d . . . O13 O 1.1096(5) 1.1097(5) 0.6507(3) 0.0429(10) Uani 1 1 d . . . O1W O 0.8059(4) 0.7504(5) 0.7859(3) 0.0343(10) Uani 1 1 d . . . H1WA H 0.8590 0.8226 0.7750 0.052 Uiso 1 1 d R . . H1WB H 0.8313 0.6738 0.7577 0.052 Uiso 1 1 d R . . O2W O 0.1663(5) 0.4772(5) 0.9749(3) 0.0447(12) Uani 1 1 d . . . H2WA H 0.2161 0.3994 0.9836 0.067 Uiso 1 1 d R . . H2WB H 0.1320 0.4815 0.9180 0.067 Uiso 1 1 d R . . O3W O 0.0801(4) 0.7661(5) 0.9629(3) 0.0436(12) Uani 1 1 d . . . H3WA H 0.0185 0.7000 0.9477 0.065 Uiso 1 1 d R . . H3WB H 0.0875 0.8228 0.9165 0.065 Uiso 1 1 d R . . O4W O 0.3673(5) 0.8663(5) 1.0289(3) 0.0409(11) Uani 1 1 d U . . H4WA H 0.4547 0.8616 1.0478 0.061 Uiso 1 1 d R . . H4WB H 0.3560 0.9154 0.9782 0.061 Uiso 1 1 d R . . O5W O 1.3134(4) 1.1394(5) 0.8029(3) 0.0326(9) Uani 1 1 d . . . H5WB H 1.3163 1.2156 0.8377 0.049 Uiso 1 1 d R . . H5WA H 1.3510 1.0668 0.8337 0.049 Uiso 1 1 d R . . O6W O 1.1008(5) 1.0652(6) 0.9255(3) 0.0522(12) Uani 1 1 d . . . H6WA H 1.0179 1.0421 0.9371 0.078 Uiso 1 1 d R . . H6WB H 1.1237 1.1477 0.9511 0.078 Uiso 1 1 d R . . O7W O 0.6842(6) 0.7167(7) 0.9769(4) 0.0692(16) Uani 1 1 d . . . H7WA H 0.6119 0.6731 0.9936 0.083 Uiso 1 1 d R . . H7WB H 0.6753 0.7271 0.9177 0.104 Uiso 1 1 d 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 V1 0.0143(4) 0.0171(5) 0.0356(5) 0.0017(4) 0.0044(3) 0.0001(4) V2 0.0219(4) 0.0264(5) 0.0297(4) -0.0018(4) 0.0029(3) -0.0027(4) V3 0.0120(4) 0.0165(5) 0.0437(5) -0.0026(4) 0.0031(3) 0.0000(3) P1 0.0129(6) 0.0183(7) 0.0306(6) 0.0006(5) 0.0040(5) 0.0003(5) P2 0.0146(6) 0.0183(8) 0.0313(7) -0.0020(5) 0.0045(5) -0.0004(5) C1 0.018(2) 0.021(3) 0.025(2) -0.003(2) 0.0001(19) -0.001(2) C2 0.026(3) 0.042(4) 0.030(3) -0.007(3) -0.006(2) -0.002(3) C3 0.044(4) 0.053(5) 0.029(3) -0.001(3) -0.010(3) 0.010(3) C4 0.062(5) 0.042(4) 0.029(3) 0.012(3) 0.002(3) 0.010(4) C5 0.023(3) 0.033(3) 0.036(3) 0.007(2) 0.007(2) 0.001(2) C6 0.018(2) 0.022(3) 0.029(3) -0.001(2) 0.002(2) 0.002(2) C7 0.022(3) 0.024(3) 0.031(3) -0.002(2) 0.000(2) 0.002(2) C8 0.017(2) 0.023(3) 0.021(2) 0.0000(19) 0.0063(18) -0.005(2) C9 0.019(2) 0.037(3) 0.036(3) 0.007(3) 0.001(2) 0.000(3) C10 0.032(3) 0.076(6) 0.026(3) -0.004(3) -0.002(2) -0.008(4) C11 0.039(4) 0.057(5) 0.039(3) -0.016(3) 0.000(3) -0.017(4) C12 0.040(4) 0.028(3) 0.046(3) -0.013(3) 0.014(3) 0.000(3) C13 0.021(3) 0.017(3) 0.029(2) 0.002(2) 0.006(2) -0.004(2) C14 0.022(3) 0.011(3) 0.047(3) -0.003(2) 0.010(2) 0.000(2) O1 0.023(2) 0.0095(19) 0.061(3) 0.0017(17) 0.0099(18) -0.0008(16) O2 0.0142(17) 0.018(2) 0.054(2) -0.0006(17) 0.0096(16) 0.0023(16) O3 0.035(2) 0.037(3) 0.0272(18) 0.0040(16) 0.0116(16) -0.0023(19) O4 0.0182(18) 0.021(2) 0.061(3) -0.0040(18) 0.0118(17) -0.0003(17) O5 0.032(2) 0.043(3) 0.0244(18) -0.0011(16) 0.0059(15) 0.0039(19) O6 0.0115(17) 0.024(2) 0.061(3) -0.0038(18) 0.0068(17) 0.0022(16) O7 0.030(2) 0.018(2) 0.057(3) -0.0101(18) -0.0130(19) 0.0012(17) O8 0.0192(18) 0.0178(19) 0.044(2) -0.0007(16) -0.0083(15) 0.0049(16) O9 0.0230(19) 0.021(2) 0.041(2) 0.0072(16) -0.0011(15) -0.0029(17) O10 0.029(2) 0.023(2) 0.053(2) 0.0116(19) -0.0027(19) -0.0024(17) O11 0.039(2) 0.046(3) 0.040(2) 0.006(2) 0.0044(19) 0.002(2) O12 0.030(2) 0.046(3) 0.042(2) 0.002(2) 0.0001(18) 0.005(2) O13 0.040(2) 0.041(3) 0.049(2) 0.000(2) 0.0085(19) -0.002(2) O1W 0.0211(18) 0.017(2) 0.063(3) 0.0019(18) -0.0009(18) 0.0062(17) O2W 0.051(3) 0.045(3) 0.039(2) -0.009(2) 0.0076(19) -0.026(2) O3W 0.0183(19) 0.067(4) 0.046(2) 0.008(2) 0.0055(17) 0.005(2) O4W 0.039(2) 0.042(3) 0.040(2) 0.0029(19) 0.0003(19) -0.015(2) O5W 0.0180(17) 0.018(2) 0.061(2) -0.0040(18) 0.0038(17) 0.0055(16) O6W 0.040(3) 0.059(3) 0.059(3) 0.008(2) 0.013(2) 0.004(2) O7W 0.067(4) 0.057(4) 0.085(4) 0.009(3) 0.013(3) -0.010(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 V1 O11 1.570(4) . ? V1 O4 1.959(4) . ? V1 O1 1.961(4) . ? V1 O9 1.993(4) . ? V1 O1W 2.030(4) . ? V2 O12 1.578(4) . ? V2 O3 1.956(4) 2_647 ? V2 O5 1.967(4) . ? V2 O2W 2.033(4) . ? V2 O4W 2.046(5) . ? V2 O3W 2.272(4) . ? V3 O13 1.570(4) . ? V3 O2 1.973(4) . ? V3 O6 1.976(4) 1_655 ? V3 O8 2.005(4) . ? V3 O5W 2.043(4) . ? V3 O6W 2.407(5) . ? P1 O1 1.499(4) . ? P1 O3 1.508(4) . ? P1 O2 1.533(4) . ? P1 C1 1.780(5) . ? P2 O5 1.501(4) . ? P2 O6 1.522(4) . ? P2 O4 1.527(4) . ? P2 C8 1.790(5) . ? C1 C2 1.392(7) . ? C1 C6 1.410(7) . ? C2 C3 1.376(9) . ? C2 H2 0.9300 . ? C3 C4 1.335(11) . ? C3 H3 0.9300 . ? C4 C5 1.420(9) . ? C4 H4 0.9300 . ? C5 C6 1.363(8) . ? C5 H5 0.9300 . ? C6 C7 1.522(7) . ? C7 O7 1.216(7) . ? C7 O8 1.283(7) . ? C8 C9 1.365(7) . ? C8 C13 1.391(7) . ? C9 C10 1.394(9) . ? C9 H9 0.9300 . ? C10 C11 1.404(11) . ? C10 H10 0.9300 . ? C11 C12 1.342(9) . ? C11 H11 0.9300 . ? C12 C13 1.388(8) . ? C12 H12 0.9300 . ? C13 C14 1.501(8) . ? C14 O9 1.253(7) . ? C14 O10 1.277(7) . ? O3 V2 1.956(3) 2_657 ? O6 V3 1.976(4) 1_455 ? O1W H1WA 0.8500 . ? O1W H1WB 0.8500 . ? O2W H2WA 0.8500 . ? O2W H2WB 0.8500 . ? O3W H3WA 0.8500 . ? O3W H3WB 0.8500 . ? O4W H4WA 0.8500 . ? O4W H4WB 0.8500 . ? O5W H5WB 0.8500 . ? O5W H5WA 0.8499 . ? O6W H6WA 0.8500 . ? O6W H6WB 0.8500 . ? O7W H7WA 0.8500 . ? O7W H7WB 0.8501 . ? 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 O11 V1 O4 108.9(2) . . ? O11 V1 O1 106.4(2) . . ? O4 V1 O1 82.32(17) . . ? O11 V1 O9 104.6(2) . . ? O4 V1 O9 88.68(17) . . ? O1 V1 O9 148.95(17) . . ? O11 V1 O1W 106.7(2) . . ? O4 V1 O1W 144.32(19) . . ? O1 V1 O1W 85.96(18) . . ? O9 V1 O1W 84.26(17) . . ? O12 V2 O3 102.89(19) . 2_647 ? O12 V2 O5 100.38(19) . . ? O3 V2 O5 156.56(19) 2_647 . ? O12 V2 O2W 95.9(2) . . ? O3 V2 O2W 91.21(18) 2_647 . ? O5 V2 O2W 89.17(18) . . ? O12 V2 O4W 99.4(2) . . ? O3 V2 O4W 84.55(18) 2_647 . ? O5 V2 O4W 88.95(18) . . ? O2W V2 O4W 164.7(2) . . ? O12 V2 O3W 174.7(2) . . ? O3 V2 O3W 77.57(16) 2_647 . ? O5 V2 O3W 79.52(16) . . ? O2W V2 O3W 78.8(2) . . ? O4W V2 O3W 85.89(19) . . ? O13 V3 O2 103.5(2) . . ? O13 V3 O6 102.9(2) . 1_655 ? O2 V3 O6 83.88(16) . 1_655 ? O13 V3 O8 101.0(2) . . ? O2 V3 O8 91.33(16) . . ? O6 V3 O8 156.05(17) 1_655 . ? O13 V3 O5W 100.0(2) . . ? O2 V3 O5W 156.23(18) . . ? O6 V3 O5W 87.63(16) 1_655 . ? O8 V3 O5W 87.47(16) . . ? O13 V3 O6W 177.6(2) . . ? O2 V3 O6W 75.89(17) . . ? O6 V3 O6W 79.34(18) 1_655 . ? O8 V3 O6W 76.73(17) . . ? O5W V3 O6W 80.74(17) . . ? O1 P1 O3 112.1(2) . . ? O1 P1 O2 109.2(2) . . ? O3 P1 O2 111.1(2) . . ? O1 P1 C1 108.0(2) . . ? O3 P1 C1 108.0(2) . . ? O2 P1 C1 108.4(2) . . ? O5 P2 O6 112.9(2) . . ? O5 P2 O4 110.9(2) . . ? O6 P2 O4 110.2(2) . . ? O5 P2 C8 105.8(2) . . ? O6 P2 C8 108.9(2) . . ? O4 P2 C8 107.9(2) . . ? C2 C1 C6 118.0(5) . . ? C2 C1 P1 119.1(4) . . ? C6 C1 P1 122.9(4) . . ? C3 C2 C1 120.2(6) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C4 C3 C2 121.8(6) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C3 C4 C5 119.7(6) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 119.2(6) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C1 121.0(5) . . ? C5 C6 C7 117.2(5) . . ? C1 C6 C7 121.7(5) . . ? O7 C7 O8 122.6(5) . . ? O7 C7 C6 118.9(5) . . ? O8 C7 C6 118.4(5) . . ? C9 C8 C13 119.2(5) . . ? C9 C8 P2 121.4(4) . . ? C13 C8 P2 119.4(4) . . ? C8 C9 C10 122.0(6) . . ? C8 C9 H9 119.0 . . ? C10 C9 H9 119.0 . . ? C9 C10 C11 117.4(6) . . ? C9 C10 H10 121.3 . . ? C11 C10 H10 121.3 . . ? C12 C11 C10 120.6(6) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 121.6(6) . . ? C11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C12 C13 C8 119.0(5) . . ? C12 C13 C14 119.3(5) . . ? C8 C13 C14 121.6(5) . . ? O9 C14 O10 121.0(5) . . ? O9 C14 C13 120.9(5) . . ? O10 C14 C13 118.1(5) . . ? P1 O1 V1 142.2(3) . . ? P1 O2 V3 129.2(2) . . ? P1 O3 V2 139.0(3) . 2_657 ? P2 O4 V1 128.8(3) . . ? P2 O5 V2 152.4(3) . . ? P2 O6 V3 140.7(2) . 1_455 ? C7 O8 V3 141.2(4) . . ? C14 O9 V1 136.5(4) . . ? V1 O1W H1WA 109.5 . . ? V1 O1W H1WB 108.7 . . ? H1WA O1W H1WB 109.5 . . ? V2 O2W H2WA 108.8 . . ? V2 O2W H2WB 109.3 . . ? H2WA O2W H2WB 109.5 . . ? V2 O3W H3WA 109.4 . . ? V2 O3W H3WB 109.4 . . ? H3WA O3W H3WB 109.5 . . ? V2 O4W H4WA 108.9 . . ? V2 O4W H4WB 109.4 . . ? H4WA O4W H4WB 109.5 . . ? V3 O5W H5WB 109.6 . . ? V3 O5W H5WA 109.0 . . ? H5WB O5W H5WA 109.5 . . ? V3 O6W H6WA 109.8 . . ? V3 O6W H6WB 108.7 . . ? H6WA O6W H6WB 109.5 . . ? H7WA O7W H7WB 109.5 . . ? 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 O1 P1 C1 C2 -10.4(5) . . . . ? O3 P1 C1 C2 -131.8(4) . . . . ? O2 P1 C1 C2 107.7(4) . . . . ? O1 P1 C1 C6 169.5(4) . . . . ? O3 P1 C1 C6 48.1(5) . . . . ? O2 P1 C1 C6 -72.3(5) . . . . ? C6 C1 C2 C3 -1.1(8) . . . . ? P1 C1 C2 C3 178.8(5) . . . . ? C1 C2 C3 C4 0.7(10) . . . . ? C2 C3 C4 C5 -1.9(11) . . . . ? C3 C4 C5 C6 3.7(10) . . . . ? C4 C5 C6 C1 -4.3(8) . . . . ? C4 C5 C6 C7 178.4(5) . . . . ? C2 C1 C6 C5 3.0(8) . . . . ? P1 C1 C6 C5 -176.9(4) . . . . ? C2 C1 C6 C7 -179.8(5) . . . . ? P1 C1 C6 C7 0.3(7) . . . . ? C5 C6 C7 O7 47.0(7) . . . . ? C1 C6 C7 O7 -130.2(6) . . . . ? C5 C6 C7 O8 -130.5(6) . . . . ? C1 C6 C7 O8 52.2(7) . . . . ? O5 P2 C8 C9 134.1(4) . . . . ? O6 P2 C8 C9 12.5(5) . . . . ? O4 P2 C8 C9 -107.1(5) . . . . ? O5 P2 C8 C13 -43.7(4) . . . . ? O6 P2 C8 C13 -165.3(4) . . . . ? O4 P2 C8 C13 75.1(4) . . . . ? C13 C8 C9 C10 0.2(8) . . . . ? P2 C8 C9 C10 -177.6(5) . . . . ? C8 C9 C10 C11 3.5(9) . . . . ? C9 C10 C11 C12 -3.0(10) . . . . ? C10 C11 C12 C13 -1.2(10) . . . . ? C11 C12 C13 C8 4.9(9) . . . . ? C11 C12 C13 C14 -176.5(6) . . . . ? C9 C8 C13 C12 -4.4(8) . . . . ? P2 C8 C13 C12 173.5(4) . . . . ? C9 C8 C13 C14 177.1(5) . . . . ? P2 C8 C13 C14 -5.0(7) . . . . ? C12 C13 C14 O9 129.3(6) . . . . ? C8 C13 C14 O9 -52.2(7) . . . . ? C12 C13 C14 O10 -49.6(7) . . . . ? C8 C13 C14 O10 128.9(6) . . . . ? O3 P1 O1 V1 -120.4(4) . . . . ? O2 P1 O1 V1 3.2(5) . . . . ? C1 P1 O1 V1 120.8(4) . . . . ? O11 V1 O1 P1 -88.6(5) . . . . ? O4 V1 O1 P1 163.8(5) . . . . ? O9 V1 O1 P1 89.4(5) . . . . ? O1W V1 O1 P1 17.6(5) . . . . ? O1 P1 O2 V3 165.0(3) . . . . ? O3 P1 O2 V3 -70.9(4) . . . . ? C1 P1 O2 V3 47.6(4) . . . . ? O13 V3 O2 P1 -86.8(4) . . . . ? O6 V3 O2 P1 171.3(3) 1_655 . . . ? O8 V3 O2 P1 14.8(3) . . . . ? O5W V3 O2 P1 101.6(5) . . . . ? O6W V3 O2 P1 90.8(3) . . . . ? O1 P1 O3 V2 20.3(5) . . . 2_657 ? O2 P1 O3 V2 -102.2(4) . . . 2_657 ? C1 P1 O3 V2 139.1(4) . . . 2_657 ? O5 P2 O4 V1 75.0(4) . . . . ? O6 P2 O4 V1 -159.2(3) . . . . ? C8 P2 O4 V1 -40.5(4) . . . . ? O11 V1 O4 P2 78.5(4) . . . . ? O1 V1 O4 P2 -176.7(4) . . . . ? O9 V1 O4 P2 -26.5(3) . . . . ? O1W V1 O4 P2 -104.7(4) . . . . ? O6 P2 O5 V2 -37.1(6) . . . . ? O4 P2 O5 V2 87.2(6) . . . . ? C8 P2 O5 V2 -156.1(5) . . . . ? O12 V2 O5 P2 -139.3(6) . . . . ? O3 V2 O5 P2 33.7(9) 2_647 . . . ? O2W V2 O5 P2 124.9(6) . . . . ? O4W V2 O5 P2 -39.9(6) . . . . ? O3W V2 O5 P2 46.1(6) . . . . ? O5 P2 O6 V3 126.2(4) . . . 1_455 ? O4 P2 O6 V3 1.5(5) . . . 1_455 ? C8 P2 O6 V3 -116.6(4) . . . 1_455 ? O7 C7 O8 V3 -176.2(4) . . . . ? C6 C7 O8 V3 1.3(9) . . . . ? O13 V3 O8 C7 48.6(6) . . . . ? O2 V3 O8 C7 -55.5(6) . . . . ? O6 V3 O8 C7 -133.3(6) 1_655 . . . ? O5W V3 O8 C7 148.3(6) . . . . ? O6W V3 O8 C7 -130.6(6) . . . . ? O10 C14 O9 V1 176.4(4) . . . . ? C13 C14 O9 V1 -2.5(8) . . . . ? O11 V1 O9 C14 -46.1(6) . . . . ? O4 V1 O9 C14 63.1(5) . . . . ? O1 V1 O9 C14 135.8(5) . . . . ? O1W V1 O9 C14 -151.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 1.559 _refine_diff_density_min -0.519 _refine_diff_density_rms 0.131 # Attachment '- compound 1a-r.cif' data_mo_20111010c_0m _database_code_depnum_ccdc_archive 'CCDC 873705' #TrackingRef '- compound 1a-r.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 O17 P2 V3' _chemical_formula_weight 671.03 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' V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-p 2ybc' 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 14.478(4) _cell_length_b 9.033(2) _cell_length_c 9.404(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.109(6) _cell_angle_gamma 90.00 _cell_volume 1222.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 756 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 21.07 _exptl_crystal_description sheet _exptl_crystal_colour blue _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 1.822 _exptl_crystal_density_diffrn 1.822 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 670 _exptl_absorpt_coefficient_mu 1.332 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.664 _exptl_absorpt_correction_T_max 0.875 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6647 _diffrn_reflns_av_R_equivalents 0.0813 _diffrn_reflns_av_sigmaI/netI 0.0920 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2137 _reflns_number_gt 1394 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; 'Since the V1 atom and associated terminal oxygen atom are disordered over two sites, some geometrical and similarity restraints are necessary in the refinement. The SADI instruction is used for O7 and V1', O6 and V1. The SIMU and DELU instructions are used for O7, V1', O6 and V1. Now there are 4 Uiso/Uij restrained atom sites, 4 distance or angle restraints and 24 least-squares restraints used in the refinement.' 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^)+(0.0949P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2137 _refine_ls_number_parameters 190 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.1073 _refine_ls_R_factor_gt 0.0640 _refine_ls_wR_factor_ref 0.1720 _refine_ls_wR_factor_gt 0.1531 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group V1 V 0.24861(9) 1.10295(12) 0.35570(12) 0.0271(4) Uani 0.85 1 d PDU . . O6 O 0.1397(3) 1.0855(6) 0.3419(6) 0.0455(12) Uani 0.85 1 d PDU . . V1' V 0.3147(6) 1.1058(8) 0.3671(7) 0.0325(9) Uani 0.15 1 d PDU . . O7 O 0.4296(12) 1.105(3) 0.388(3) 0.027(2) Uani 0.15 1 d PDU . . V2 V 0.49182(13) 1.0453(2) -0.0410(2) 0.0337(6) Uani 0.50 1 d P . . P1 P 0.28599(11) 1.08479(16) 0.03107(17) 0.0294(4) Uani 1 1 d . . . C1 C 0.1919(4) 0.9559(6) 0.0139(6) 0.0296(13) Uani 1 1 d . . . C2 C 0.1955(4) 0.8293(6) 0.1002(6) 0.0291(13) Uani 1 1 d . . . C3 C 0.1248(4) 0.7255(7) 0.0769(7) 0.0424(16) Uani 1 1 d . . . H3 H 0.1273 0.6401 0.1324 0.051 Uiso 1 1 calc R . . C4 C 0.0512(5) 0.7462(9) -0.0263(8) 0.057(2) Uani 1 1 d . . . H4 H 0.0046 0.6752 -0.0413 0.068 Uiso 1 1 calc R . . C5 C 0.0474(4) 0.8728(9) -0.1064(8) 0.053(2) Uani 1 1 d . . . H5 H -0.0034 0.8895 -0.1735 0.064 Uiso 1 1 calc R . . C6 C 0.1175(4) 0.9755(7) -0.0893(7) 0.0406(16) Uani 1 1 d . . . H6 H 0.1150 1.0588 -0.1477 0.049 Uiso 1 1 calc R . . C7 C 0.2713(4) 0.8030(6) 0.2177(6) 0.0326(14) Uani 1 1 d . . . O1 O 0.2834(3) 1.1697(4) 0.1705(4) 0.0397(11) Uani 1 1 d . . . O2 O 0.3748(3) 0.9968(5) 0.0310(5) 0.0420(11) Uani 1 1 d . . . O3 O 0.2726(3) 1.1907(4) -0.0933(4) 0.0448(12) Uani 1 1 d . . . O4 O 0.2930(3) 0.9025(4) 0.3107(5) 0.0382(11) Uani 1 1 d . . . O5 O 0.3116(3) 0.6811(4) 0.2245(5) 0.0432(12) Uani 1 1 d . . . O8 O 0.4676(6) 1.1411(14) -0.1709(10) 0.069(3) Uani 0.50 1 d P . . O1W O 0.2912(3) 1.0566(5) 0.5598(4) 0.0481(13) Uani 1 1 d . . . H1WA H 0.2938 0.9672 0.5881 0.058 Uiso 1 1 d R . . H1WB H 0.2921 1.1242 0.6228 0.058 Uiso 1 1 d R . . O2W O 0.5260(4) 1.1583(7) 0.1322(6) 0.089(2) Uani 1 1 d . . . H2WA H 0.4838 1.1942 0.1781 0.107 Uiso 1 1 d R . . H2WB H 0.5803 1.1945 0.1484 0.107 Uiso 1 1 d 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 V1 0.0410(7) 0.0209(6) 0.0192(6) -0.0004(5) 0.0024(5) 0.0036(5) O6 0.0411(12) 0.049(3) 0.045(3) -0.002(2) 0.000(2) 0.005(2) V1' 0.0429(11) 0.0286(18) 0.0260(19) -0.0009(18) 0.0041(19) 0.0026(19) O7 0.0425(15) 0.023(5) 0.018(5) -0.004(5) 0.009(5) -0.003(5) V2 0.0297(11) 0.0406(13) 0.0307(13) -0.0005(9) 0.0034(10) -0.0030(10) P1 0.0419(9) 0.0243(8) 0.0227(9) -0.0002(7) 0.0061(7) -0.0025(6) C1 0.034(3) 0.032(3) 0.024(3) -0.001(3) 0.009(2) 0.004(2) C2 0.034(3) 0.025(3) 0.029(3) -0.003(3) 0.008(3) -0.002(2) C3 0.049(4) 0.040(4) 0.039(4) -0.003(3) 0.008(3) -0.014(3) C4 0.042(4) 0.069(5) 0.058(5) -0.011(4) 0.003(4) -0.022(4) C5 0.027(3) 0.083(6) 0.046(4) -0.013(4) -0.011(3) 0.008(3) C6 0.035(3) 0.048(4) 0.037(4) 0.001(3) -0.001(3) 0.011(3) C7 0.045(3) 0.024(3) 0.028(3) -0.003(3) 0.001(3) 0.002(3) O1 0.079(3) 0.022(2) 0.019(2) -0.0013(18) 0.012(2) -0.004(2) O2 0.033(2) 0.048(3) 0.045(3) -0.007(2) 0.005(2) -0.0034(19) O3 0.087(3) 0.026(2) 0.022(2) 0.0026(19) 0.010(2) -0.005(2) O4 0.056(3) 0.026(2) 0.032(2) -0.001(2) -0.002(2) 0.0069(19) O5 0.065(3) 0.026(2) 0.036(3) -0.003(2) -0.007(2) 0.008(2) O8 0.036(5) 0.123(10) 0.050(7) 0.041(7) 0.021(5) 0.017(5) O1W 0.095(4) 0.024(2) 0.023(2) 0.0035(19) -0.006(2) -0.002(2) O2W 0.045(3) 0.124(5) 0.100(5) -0.078(4) 0.010(3) -0.015(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 V1 V1' 0.952(8) . ? V1 O6 1.576(5) . ? V1 O3 1.947(4) 4_586 ? V1 O1 1.959(4) . ? V1 O4 1.982(4) . ? V1 O1W 1.997(4) . ? V1' O7 1.653(17) . ? V1' O4 1.928(8) . ? V1' O1W 1.932(9) . ? V1' O1 1.944(8) . ? V1' O3 1.984(8) 4_586 ? V2 V2 1.131(4) 3_675 ? V2 O8 1.508(9) . ? V2 O2 1.940(5) . ? V2 O2W 1.941(5) . ? V2 O2 1.961(4) 3_675 ? V2 O2W 2.034(6) 3_675 ? P1 O3 1.507(4) . ? P1 O2 1.511(4) . ? P1 O1 1.523(4) . ? P1 C1 1.786(6) . ? C1 C6 1.383(8) . ? C1 C2 1.400(8) . ? C2 C3 1.388(8) . ? C2 C7 1.491(8) . ? C3 C4 1.376(9) . ? C3 H3 0.9300 . ? C4 C5 1.367(10) . ? C4 H4 0.9300 . ? C5 C6 1.372(9) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O5 1.244(7) . ? C7 O4 1.270(7) . ? O2 V2 1.961(4) 3_675 ? O3 V1 1.947(4) 4_585 ? O3 V1' 1.984(8) 4_585 ? O1W H1WA 0.8500 . ? O1W H1WB 0.8500 . ? O2W V2 2.034(6) 3_675 ? O2W H2WA 0.8499 . ? O2W H2WB 0.8501 . ? 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 V1' V1 O6 175.5(5) . . ? V1' V1 O3 78.2(4) . 4_586 ? O6 V1 O3 105.5(2) . 4_586 ? V1' V1 O1 75.0(5) . . ? O6 V1 O1 107.9(2) . . ? O3 V1 O1 82.40(18) 4_586 . ? V1' V1 O4 72.8(4) . . ? O6 V1 O4 103.6(2) . . ? O3 V1 O4 150.9(2) 4_586 . ? O1 V1 O4 88.39(19) . . ? V1' V1 O1W 72.2(5) . . ? O6 V1 O1W 105.2(2) . . ? O3 V1 O1W 86.30(17) 4_586 . ? O1 V1 O1W 146.8(2) . . ? O4 V1 O1W 86.53(18) . . ? V1 V1' O7 178.2(10) . . ? V1 V1' O4 79.1(5) . . ? O7 V1' O4 99.2(9) . . ? V1 V1' O1W 79.8(5) . . ? O7 V1' O1W 99.5(9) . . ? O4 V1' O1W 89.9(4) . . ? V1 V1' O1 76.8(4) . . ? O7 V1' O1 104.0(9) . . ? O4 V1' O1 90.4(3) . . ? O1W V1' O1 156.1(5) . . ? V1 V1' O3 73.8(4) . 4_586 ? O7 V1' O3 107.9(9) . 4_586 ? O4 V1' O3 152.9(5) . 4_586 ? O1W V1' O3 87.1(3) . 4_586 ? O1 V1' O3 81.8(3) . 4_586 ? V2 V2 O8 168.7(6) 3_675 . ? V2 V2 O2 74.1(2) 3_675 . ? O8 V2 O2 106.0(4) . . ? V2 V2 O2W 78.0(3) 3_675 . ? O8 V2 O2W 113.2(5) . . ? O2 V2 O2W 88.9(2) . . ? V2 V2 O2 72.2(2) 3_675 3_675 ? O8 V2 O2 107.0(4) . 3_675 ? O2 V2 O2 146.29(13) . 3_675 ? O2W V2 O2 84.3(2) . 3_675 ? V2 V2 O2W 69.0(3) 3_675 3_675 ? O8 V2 O2W 99.8(5) . 3_675 ? O2 V2 O2W 82.4(2) . 3_675 ? O2W V2 O2W 147.03(14) . 3_675 ? O2 V2 O2W 85.7(2) 3_675 3_675 ? O3 P1 O2 111.8(3) . . ? O3 P1 O1 109.6(2) . . ? O2 P1 O1 111.4(2) . . ? O3 P1 C1 108.1(3) . . ? O2 P1 C1 107.3(3) . . ? O1 P1 C1 108.5(3) . . ? C6 C1 C2 119.3(6) . . ? C6 C1 P1 120.6(5) . . ? C2 C1 P1 120.0(4) . . ? C3 C2 C1 118.6(5) . . ? C3 C2 C7 118.8(5) . . ? C1 C2 C7 122.6(5) . . ? C4 C3 C2 121.5(7) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C5 C4 C3 119.0(6) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 121.1(6) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C1 120.4(6) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? O5 C7 O4 120.7(5) . . ? O5 C7 C2 118.9(5) . . ? O4 C7 C2 120.4(5) . . ? P1 O1 V1' 130.1(3) . . ? P1 O1 V1 130.0(2) . . ? V1' O1 V1 28.2(2) . . ? P1 O2 V2 131.0(3) . . ? P1 O2 V2 159.3(3) . 3_675 ? V2 O2 V2 33.71(13) . 3_675 ? P1 O3 V1 143.4(3) . 4_585 ? P1 O3 V1' 135.8(3) . 4_585 ? V1 O3 V1' 28.0(2) 4_585 4_585 ? C7 O4 V1' 152.2(4) . . ? C7 O4 V1 137.0(4) . . ? V1' O4 V1 28.1(2) . . ? V1' O1W V1 28.0(2) . . ? V1' O1W H1WA 120.4 . . ? V1 O1W H1WA 119.9 . . ? V1' O1W H1WB 119.8 . . ? V1 O1W H1WB 119.9 . . ? H1WA O1W H1WB 117.9 . . ? V2 O2W V2 32.97(14) . 3_675 ? V2 O2W H2WA 119.6 . . ? V2 O2W H2WA 119.6 3_675 . ? V2 O2W H2WB 120.1 . . ? V2 O2W H2WB 119.8 3_675 . ? H2WA O2W H2WB 117.6 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.985 _refine_diff_density_min -0.939 _refine_diff_density_rms 0.108