# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/279 data_s97 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H15 O5 P S' _chemical_formula_weight 230.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'S' 'S' 0.1246 0.1234 '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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/a 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 10.074(1) _cell_length_b 8.3570(9) _cell_length_c 13.991(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.46(1) _cell_angle_gamma 90.00 _cell_volume 1117.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.23 _cell_measurement_theta_max 21.04 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.423 _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 'CAD4 Mach3' _diffrn_measurement_method \t/2\t _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% -1.0 _diffrn_reflns_number 2040 _diffrn_reflns_av_R_equivalents 0.0083 _diffrn_reflns_av_sigmaI/netI 0.0270 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1958 _reflns_number_gt 1463 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Software' _computing_cell_refinement 'CAD4 Software' _computing_data_reduction MolEN _computing_structure_solution 'SIR92' _computing_structure_refinement 'SHELXL-97' _computing_molecular_graphics 'ZORTEP' _computing_publication_material 'PARST95, WinGX' _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^)+(0.0743P)^2^+0.6371P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1958 _refine_ls_number_parameters 121 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0699 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1349 _refine_ls_wR_factor_gt 0.1197 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 S S 0.16686(8) 0.15267(8) 0.57499(6) 0.0403(3) Uani 1 1 d . . . P P 0.23038(9) 0.37770(10) 0.75171(7) 0.0465(3) Uani 1 1 d . . . O1 O 0.1045(2) 0.0576(3) 0.63519(18) 0.0573(7) Uani 1 1 d . . . O2 O 0.2386(2) 0.0702(3) 0.51591(19) 0.0572(7) Uani 1 1 d . . . O3 O 0.0849(2) 0.4298(3) 0.71423(19) 0.0607(7) Uani 1 1 d . . . O4 O 0.3414(3) 0.5106(3) 0.79637(19) 0.0591(7) Uani 1 1 d . . . O5 O 0.2697(3) 0.2578(3) 0.84147(19) 0.0710(8) Uani 1 1 d . . . C1 C 0.0394(3) 0.2757(4) 0.4951(3) 0.0466(8) Uani 1 1 d . . . H1A H 0.0820 0.3441 0.4580 0.070 Uiso 1 1 calc R . . H1B H -0.0031 0.3398 0.5344 0.070 Uiso 1 1 calc R . . H1C H -0.0308 0.2107 0.4490 0.070 Uiso 1 1 calc R . . C2 C 0.2889(3) 0.2850(4) 0.6561(2) 0.0418(7) Uani 1 1 d . . . H2A H 0.3116 0.3684 0.6156 0.050 Uiso 1 1 calc R . . H2B H 0.3743 0.2263 0.6888 0.050 Uiso 1 1 calc R . . C41 C 0.3374(7) 0.6602(5) 0.7450(4) 0.1037(19) Uani 1 1 d . . . H41A H 0.3637 0.6418 0.6850 0.124 Uiso 1 1 calc R . . H41B H 0.2421 0.7002 0.7236 0.124 Uiso 1 1 calc R . . C42 C 0.4231(8) 0.7740(7) 0.8021(5) 0.152(3) Uani 1 1 d . . . H42A H 0.3848 0.8116 0.8527 0.227 Uiso 1 1 calc R . . H42B H 0.4309 0.8618 0.7599 0.227 Uiso 1 1 calc R . . H42C H 0.5140 0.7289 0.8340 0.227 Uiso 1 1 calc R . . C51 C 0.1695(6) 0.1776(9) 0.8769(4) 0.130(2) Uani 1 1 d . . . H51A H 0.1006 0.2555 0.8818 0.156 Uiso 1 1 calc R . . H51B H 0.1213 0.0995 0.8266 0.156 Uiso 1 1 calc R . . C52 C 0.2173(9) 0.1042(9) 0.9636(5) 0.168(3) Uani 1 1 d . . . H52A H 0.2905 0.0318 0.9619 0.253 Uiso 1 1 calc R . . H52B H 0.1428 0.0454 0.9764 0.253 Uiso 1 1 calc R . . H52C H 0.2536 0.1816 1.0161 0.253 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 S 0.0407(4) 0.0274(4) 0.0546(5) -0.0058(3) 0.0177(4) -0.0021(3) P 0.0492(5) 0.0419(5) 0.0523(5) -0.0087(4) 0.0213(4) -0.0062(4) O1 0.0653(15) 0.0394(13) 0.0689(16) 0.0020(12) 0.0236(13) -0.0136(11) O2 0.0515(13) 0.0503(13) 0.0713(16) -0.0204(12) 0.0216(12) 0.0069(11) O3 0.0511(14) 0.0610(15) 0.0751(17) -0.0169(13) 0.0273(13) 0.0031(12) O4 0.0684(16) 0.0480(14) 0.0598(15) -0.0128(12) 0.0186(13) -0.0162(12) O5 0.0745(18) 0.0755(19) 0.0670(17) 0.0150(15) 0.0282(14) -0.0101(15) C1 0.0423(17) 0.0382(17) 0.0578(19) -0.0039(15) 0.0135(15) -0.0017(14) C2 0.0359(16) 0.0352(16) 0.0559(19) -0.0067(15) 0.0167(14) -0.0033(13) C41 0.152(5) 0.058(3) 0.089(3) 0.002(3) 0.022(3) -0.043(3) C42 0.206(7) 0.089(4) 0.143(6) 0.004(4) 0.032(5) -0.076(5) C51 0.128(5) 0.165(6) 0.103(4) 0.039(4) 0.046(4) -0.052(4) C52 0.242(8) 0.176(8) 0.094(4) 0.037(5) 0.063(5) -0.065(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 S O2 1.435(2) . ? S O1 1.439(2) . ? S C1 1.745(3) . ? S C2 1.772(3) . ? P O3 1.458(2) . ? P O5 1.557(3) . ? P O4 1.560(2) . ? P C2 1.799(3) . ? O4 C41 1.436(5) . ? O5 C51 1.426(5) . ? C41 C42 1.361(7) . ? C51 C52 1.306(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 O2 S O1 117.70(15) . . ? O2 S C1 108.45(16) . . ? O1 S C1 109.35(15) . . ? O2 S C2 107.14(14) . . ? O1 S C2 108.23(15) . . ? C1 S C2 105.26(15) . . ? O3 P O5 116.90(16) . . ? O3 P O4 116.32(15) . . ? O5 P O4 99.68(15) . . ? O3 P C2 112.96(15) . . ? O5 P C2 105.24(16) . . ? O4 P C2 104.01(14) . . ? C41 O4 P 121.1(3) . . ? C51 O5 P 123.8(3) . . ? S C2 P 114.87(16) . . ? C42 C41 O4 113.7(4) . . ? C52 C51 O5 116.8(6) . . ? 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 O3 P O4 C41 -45.8(4) . . . . ? O5 P O4 C41 -172.5(4) . . . . ? C2 P O4 C41 79.0(4) . . . . ? O3 P O5 C51 10.8(5) . . . . ? O4 P O5 C51 137.0(4) . . . . ? C2 P O5 C51 -115.5(4) . . . . ? O2 S C2 P -170.34(17) . . . . ? O1 S C2 P -42.5(2) . . . . ? C1 S C2 P 74.4(2) . . . . ? O3 P C2 S -41.8(2) . . . . ? O5 P C2 S 86.9(2) . . . . ? O4 P C2 S -168.80(17) . . . . ? P O4 C41 C42 167.9(5) . . . . ? P O5 C51 C52 -167.6(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.284 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.060