# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1765 data_peroxo _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C32 H40 O10 P2' _chemical_formula_weight 646.58 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 15.447(3) _cell_length_b 10.989(2) _cell_length_c 19.907(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3379.2(11) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 904 _cell_measurement_theta_min 5 _cell_measurement_theta_max 24 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method ? _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 0.182 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 IPDS(Stoe) _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11022 _diffrn_reflns_av_R_equivalents 0.0485 _diffrn_reflns_av_sigmaI/netI 0.0544 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 26.90 _reflns_number_total 3414 _reflns_number_observed 2081 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 637 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0532P)^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 0.0012(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2777 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0663 _refine_ls_R_factor_obs 0.0362 _refine_ls_wR_factor_all 0.0940 _refine_ls_wR_factor_obs 0.0821 _refine_ls_goodness_of_fit_all 0.934 _refine_ls_goodness_of_fit_obs 1.044 _refine_ls_restrained_S_all 0.935 _refine_ls_restrained_S_obs 1.044 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P1 P 0.06509(3) 0.98584(3) 0.09799(2) 0.02197(14) Uani 1 d . . O1 O 0.02745(9) 1.09661(10) 0.13220(7) 0.0298(3) Uani 1 d . . C1 C 0.04848(12) 0.99244(14) 0.00830(9) 0.0239(4) Uani 1 d . . H1A H 0.08135(12) 1.06179(14) -0.01060(9) 0.029 Uiso 1 calc R . H1B H 0.07049(12) 0.91681(14) -0.01264(9) 0.029 Uiso 1 calc R . C2 C 0.17967(14) 0.97418(14) 0.11162(10) 0.0283(5) Uani 1 d . . C3 C 0.2224(2) 1.0555(2) 0.15257(13) 0.0500(7) Uani 1 d . . H3A H 0.1908(2) 1.1192(2) 0.17358(13) 0.060 Uiso 1 calc R . C4 C 0.3105(2) 1.0457(2) 0.16351(15) 0.0604(8) Uani 1 d . . H4 H 0.3386(2) 1.1026(2) 0.19206(15) 0.073 Uiso 1 calc R . C5 C 0.3576(2) 0.9556(2) 0.13395(14) 0.0495(7) Uani 1 d . . H5A H 0.4179(2) 0.9485(2) 0.14216(14) 0.059 Uiso 1 calc R . C6 C 0.3159(2) 0.8750(3) 0.0919(2) 0.0952(14) Uani 1 d . . H6 H 0.3481(2) 0.8126(3) 0.0703(2) 0.114 Uiso 1 calc R . C7 C 0.2287(2) 0.8839(2) 0.0808(2) 0.0868(13) Uani 1 d . . H7 H 0.2012(2) 0.8275(2) 0.0517(2) 0.104 Uiso 1 calc R . C8 C 0.01562(13) 0.84651(14) 0.12780(10) 0.0248(4) Uani 1 d . . C9 C -0.00491(15) 0.8395(2) 0.19566(11) 0.0337(5) Uani 1 d . . H9 H 0.00626(15) 0.9068(2) 0.22435(11) 0.040 Uiso 1 calc R . C10 C -0.0418(2) 0.7340(2) 0.22161(12) 0.0426(6) Uani 1 d . . H10 H -0.0547(2) 0.7288(2) 0.26818(12) 0.051 Uiso 1 calc R . C11 C -0.0599(2) 0.6364(2) 0.17989(13) 0.0436(6) Uani 1 d . . H11 H -0.0859(2) 0.5651(2) 0.19777(13) 0.052 Uiso 1 calc R . C12 C -0.0400(2) 0.6425(2) 0.11234(12) 0.0420(6) Uani 1 d . . H12 H -0.0526(2) 0.5755(2) 0.08385(12) 0.050 Uiso 1 calc R . C13 C -0.00156(14) 0.7467(2) 0.08581(11) 0.0334(5) Uani 1 d . . H13 H 0.01299(14) 0.7502(2) 0.03948(11) 0.040 Uiso 1 calc R . C14 C -0.17761(15) 0.2990(2) 0.12690(13) 0.0386(6) Uani 1 d . . C15 C -0.2157(2) 0.3611(2) 0.0657(2) 0.0695(9) Uani 1 d . . H15A H -0.1779(7) 0.3475(16) 0.0269(3) 0.104 Uiso 1 calc R . H15B H -0.2207(13) 0.4486(4) 0.0743(4) 0.104 Uiso 1 calc R . H15C H -0.2732(6) 0.3273(14) 0.0565(6) 0.104 Uiso 1 calc R . C16 C -0.2248(2) 0.3288(2) 0.1915(2) 0.0613(8) Uani 1 d . . H16A H -0.1939(7) 0.2925(15) 0.2295(2) 0.092 Uiso 1 calc R . H16B H -0.2837(4) 0.2960(15) 0.1895(4) 0.092 Uiso 1 calc R . H16C H -0.2273(11) 0.4173(2) 0.1973(5) 0.092 Uiso 1 calc R . O2 O -0.09133(10) 0.33751(10) 0.14034(7) 0.0338(4) Uani 1 d . . O3 O -0.03631(11) 0.31275(13) 0.08203(8) 0.0419(4) Uani 1 d . . H3 H -0.0148(18) 0.2492(24) 0.0923(14) 0.055(8) Uiso 1 d . . O4 O -0.17873(11) 0.17273(12) 0.10980(10) 0.0499(5) Uani 1 d . . O5 O -0.14969(14) 0.10110(13) 0.16717(11) 0.0605(6) Uani 1 d . . H5 H -0.0934(22) 0.1012(24) 0.1619(16) 0.073(10) Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0246(3) 0.0204(2) 0.0209(2) -0.0007(2) -0.0033(2) 0.0019(2) O1 0.0355(9) 0.0250(6) 0.0288(8) -0.0046(5) -0.0018(7) 0.0043(5) C1 0.0245(12) 0.0271(8) 0.0201(9) 0.0026(7) 0.0009(8) 0.0008(7) C2 0.0295(12) 0.0240(8) 0.0314(11) 0.0013(7) -0.0060(9) -0.0004(7) C3 0.0321(15) 0.0628(14) 0.055(2) -0.0297(12) 0.0011(12) -0.0028(11) C4 0.036(2) 0.080(2) 0.065(2) -0.0325(14) -0.0070(14) -0.0129(12) C5 0.0276(14) 0.0469(12) 0.074(2) 0.0045(11) -0.0168(13) -0.0021(9) C6 0.042(2) 0.065(2) 0.179(4) -0.061(2) -0.037(2) 0.0259(14) C7 0.038(2) 0.065(2) 0.158(4) -0.068(2) -0.041(2) 0.0222(13) C8 0.0253(12) 0.0236(8) 0.0254(11) 0.0023(7) -0.0038(9) 0.0025(7) C9 0.0363(14) 0.0370(9) 0.0278(11) 0.0025(8) -0.0040(10) -0.0021(8) C10 0.044(2) 0.0503(12) 0.0339(12) 0.0177(9) 0.0013(11) -0.0020(10) C11 0.0407(15) 0.0322(10) 0.058(2) 0.0179(9) -0.0027(13) -0.0027(9) C12 0.049(2) 0.0236(9) 0.053(2) 0.0009(8) -0.0066(12) -0.0016(8) C13 0.0436(14) 0.0252(9) 0.0313(12) -0.0007(7) -0.0028(10) 0.0031(8) C14 0.0279(13) 0.0309(9) 0.0569(15) -0.0090(9) -0.0003(11) 0.0023(8) C15 0.066(2) 0.063(2) 0.079(2) -0.0100(14) -0.031(2) 0.0270(14) C16 0.048(2) 0.0523(13) 0.084(2) -0.0080(13) 0.026(2) 0.0067(11) O2 0.0348(9) 0.0299(6) 0.0369(9) -0.0090(5) 0.0030(7) 0.0011(6) O3 0.0448(11) 0.0358(8) 0.0451(10) 0.0064(6) 0.0136(8) 0.0055(7) O4 0.0345(10) 0.0336(7) 0.0816(13) -0.0150(7) -0.0067(9) -0.0012(6) O5 0.0485(13) 0.0374(8) 0.096(2) 0.0174(8) 0.0235(12) 0.0008(8) _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 O1 1.5112(12) . ? P1 C2 1.795(2) . ? P1 C1 1.805(2) . ? P1 C8 1.811(2) . ? C1 C1 1.543(4) 5_575 ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 C3 1.377(3) . ? C2 C7 1.390(3) . ? C3 C4 1.382(4) . ? C3 H3A 0.95 . ? C4 C5 1.362(4) . ? C4 H4 0.95 . ? C5 C6 1.379(4) . ? C5 H5A 0.95 . ? C6 C7 1.368(4) . ? C6 H6 0.95 . ? C7 H7 0.95 . ? C8 C9 1.390(3) . ? C8 C13 1.404(3) . ? C9 C10 1.392(3) . ? C9 H9 0.95 . ? C10 C11 1.384(3) . ? C10 H10 0.95 . ? C11 C12 1.381(3) . ? C11 H11 0.95 . ? C12 C13 1.393(3) . ? C12 H12 0.95 . ? C13 H13 0.95 . ? C14 O2 1.424(3) . ? C14 O4 1.428(2) . ? C14 C16 1.514(4) . ? C14 C15 1.515(4) . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? C16 H16A 0.98 . ? C16 H16B 0.98 . ? C16 H16C 0.98 . ? O2 O3 1.464(2) . ? O3 H3 0.80(3) . ? O4 O5 1.458(3) . ? O5 H5 0.88(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 O1 P1 C2 111.63(8) . . ? O1 P1 C1 111.02(8) . . ? C2 P1 C1 107.01(9) . . ? O1 P1 C8 111.77(9) . . ? C2 P1 C8 107.83(8) . . ? C1 P1 C8 107.34(8) . . ? C1 C1 P1 110.7(2) 5_575 . ? C1 C1 H1A 109.50(12) 5_575 . ? P1 C1 H1A 109.50(6) . . ? C1 C1 H1B 109.50(12) 5_575 . ? P1 C1 H1B 109.50(5) . . ? H1A C1 H1B 108.1 . . ? C3 C2 C7 117.6(2) . . ? C3 C2 P1 121.0(2) . . ? C7 C2 P1 121.4(2) . . ? C2 C3 C4 120.9(2) . . ? C2 C3 H3A 119.53(14) . . ? C4 C3 H3A 119.53(13) . . ? C5 C4 C3 121.0(2) . . ? C5 C4 H4 119.5(2) . . ? C3 C4 H4 119.52(13) . . ? C4 C5 C6 118.7(2) . . ? C4 C5 H5A 120.7(2) . . ? C6 C5 H5A 120.7(2) . . ? C7 C6 C5 120.8(2) . . ? C7 C6 H6 119.6(2) . . ? C5 C6 H6 119.6(2) . . ? C6 C7 C2 121.1(2) . . ? C6 C7 H7 119.4(2) . . ? C2 C7 H7 119.45(14) . . ? C9 C8 C13 119.5(2) . . ? C9 C8 P1 117.49(13) . . ? C13 C8 P1 123.02(15) . . ? C8 C9 C10 120.0(2) . . ? C8 C9 H9 119.98(10) . . ? C10 C9 H9 119.98(14) . . ? C11 C10 C9 120.3(2) . . ? C11 C10 H10 119.84(13) . . ? C9 C10 H10 119.84(13) . . ? C12 C11 C10 120.1(2) . . ? C12 C11 H11 119.93(11) . . ? C10 C11 H11 119.93(13) . . ? C11 C12 C13 120.2(2) . . ? C11 C12 H12 119.88(11) . . ? C13 C12 H12 119.88(13) . . ? C12 C13 C8 119.8(2) . . ? C12 C13 H13 120.12(13) . . ? C8 C13 H13 120.12(11) . . ? O2 C14 O4 110.2(2) . . ? O2 C14 C16 103.1(2) . . ? O4 C14 C16 114.0(2) . . ? O2 C14 C15 112.4(2) . . ? O4 C14 C15 104.0(2) . . ? C16 C14 C15 113.4(2) . . ? C14 C15 H15A 109.5(2) . . ? C14 C15 H15B 109.47(13) . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5(2) . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.47(15) . . ? C14 C16 H16B 109.47(14) . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.47(12) . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 O2 O3 109.82(15) . . ? O2 O3 H3 101.6(20) . . ? C14 O4 O5 109.5(2) . . ? O4 O5 H5 102.2(21) . . ? _refine_diff_density_max 0.279 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.039