Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_section_title ;Phosphonioalkylthiosulfate zwitterions new masked thiolate ligands for the formation of cationic functionalised gold nanoparticles ; _publ_contact_author_name 'Neil Bricklebank' _publ_contact_author_email N.BRICKLEBANK@SHU.AC.UK loop_ _publ_author_name 'Neil Bricklebank' 'David W. Allen' 'Philip Gardiner' 'Michael B. Hursthouse' 'Ju-Nam Yon.' ; M.E.Light ; data_03src0357 _database_code_depnum_ccdc_archive 'CCDC 243256' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 O3 P S2' _chemical_formula_weight 416.47 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' S S 0.1246 0.1234 '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/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 11.6475(3) _cell_length_b 14.2692(3) _cell_length_c 12.0730(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.5610(10) _cell_angle_gamma 90.00 _cell_volume 1923.30(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.380 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9530 _exptl_absorpt_correction_T_max 0.9924 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6267 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.0600 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3381 _reflns_number_gt 2700 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski and MInor, 1997)' _computing_data_reduction 'DENZO, COLLECT, MAXUS (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^)+(0.0454P)^2^+0.9614P] 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 none _refine_ls_number_reflns 3381 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1068 _refine_ls_wR_factor_gt 0.0994 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.005 _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 C1 C 0.9851(2) 0.14913(17) 0.2065(2) 0.0182(6) Uani 1 1 d . . . C2 C 1.0579(2) 0.18931(19) 0.3079(2) 0.0237(6) Uani 1 1 d . . . H2 H 1.0814 0.2531 0.3088 0.028 Uiso 1 1 calc R . . C3 C 1.0952(2) 0.1356(2) 0.4066(2) 0.0274(6) Uani 1 1 d . . . H3 H 1.1427 0.1631 0.4763 0.033 Uiso 1 1 calc R . . C4 C 1.0639(2) 0.0418(2) 0.4045(2) 0.0259(6) Uani 1 1 d . . . H4 H 1.0923 0.0048 0.4723 0.031 Uiso 1 1 calc R . . C5 C 0.9917(2) 0.00153(19) 0.3047(2) 0.0232(6) Uani 1 1 d . . . H5 H 0.9694 -0.0626 0.3040 0.028 Uiso 1 1 calc R . . C6 C 0.9521(2) 0.05560(18) 0.2055(2) 0.0198(6) Uani 1 1 d . . . H6 H 0.9022 0.0285 0.1366 0.024 Uiso 1 1 calc R . . C7 C 0.8313(2) 0.15578(16) -0.0293(2) 0.0171(5) Uani 1 1 d . . . C8 C 0.8469(2) 0.12843(17) -0.1349(2) 0.0201(6) Uani 1 1 d . . . H8 H 0.9174 0.1458 -0.1546 0.024 Uiso 1 1 calc R . . C9 C 0.7589(2) 0.07576(18) -0.2111(2) 0.0225(6) Uani 1 1 d . . . H9 H 0.7694 0.0568 -0.2831 0.027 Uiso 1 1 calc R . . C10 C 0.6555(2) 0.05060(17) -0.1829(2) 0.0224(6) Uani 1 1 d . . . H10 H 0.5961 0.0139 -0.2352 0.027 Uiso 1 1 calc R . . C11 C 0.6387(2) 0.07900(17) -0.0782(2) 0.0216(6) Uani 1 1 d . . . H11 H 0.5677 0.0620 -0.0592 0.026 Uiso 1 1 calc R . . C12 C 0.7259(2) 0.13212(17) -0.0020(2) 0.0198(6) Uani 1 1 d . . . H12 H 0.7142 0.1525 0.0689 0.024 Uiso 1 1 calc R . . C13 C 0.8926(2) 0.33120(17) 0.1051(2) 0.0174(5) Uani 1 1 d . . . C14 C 0.8947(2) 0.40399(18) 0.0278(2) 0.0206(6) Uani 1 1 d . . . H14 H 0.9210 0.3924 -0.0386 0.025 Uiso 1 1 calc R . . C15 C 0.8580(2) 0.49307(18) 0.0489(2) 0.0232(6) Uani 1 1 d . . . H15 H 0.8595 0.5428 -0.0031 0.028 Uiso 1 1 calc R . . C16 C 0.8194(2) 0.50970(18) 0.1449(2) 0.0234(6) Uani 1 1 d . . . H16 H 0.7957 0.5711 0.1596 0.028 Uiso 1 1 calc R . . C17 C 0.8149(2) 0.43782(19) 0.2197(2) 0.0254(6) Uani 1 1 d . . . H17 H 0.7870 0.4497 0.2850 0.030 Uiso 1 1 calc R . . C18 C 0.8508(2) 0.34831(18) 0.2004(2) 0.0223(6) Uani 1 1 d . . . H18 H 0.8469 0.2988 0.2518 0.027 Uiso 1 1 calc R . . C19 C 1.0772(2) 0.23698(17) 0.0300(2) 0.0184(5) Uani 1 1 d . . . H19A H 1.0517 0.2566 -0.0520 0.022 Uiso 1 1 calc R . . H19B H 1.1232 0.2894 0.0754 0.022 Uiso 1 1 calc R . . C20 C 1.1604(2) 0.15262(17) 0.0415(2) 0.0214(6) Uani 1 1 d . . . H20A H 1.1957 0.1376 0.1244 0.026 Uiso 1 1 calc R . . H20B H 1.1137 0.0976 0.0038 0.026 Uiso 1 1 calc R . . C21 C 1.2605(2) 0.17212(19) -0.0137(2) 0.0238(6) Uani 1 1 d . . . H21A H 1.2242 0.1854 -0.0968 0.029 Uiso 1 1 calc R . . H21B H 1.3098 0.1148 -0.0079 0.029 Uiso 1 1 calc R . . O1 O 1.42085(16) 0.16945(13) 0.26735(14) 0.0274(4) Uani 1 1 d . . . O2 O 1.52510(15) 0.11982(13) 0.13043(14) 0.0260(4) Uani 1 1 d . . . O3 O 1.57140(17) 0.27069(13) 0.22834(17) 0.0353(5) Uani 1 1 d . . . P1 P 0.94498(5) 0.21794(4) 0.07675(5) 0.01666(18) Uani 1 1 d . . . S1 S 1.35837(6) 0.26926(5) 0.05006(6) 0.02483(19) Uani 1 1 d . . . S2 S 1.48354(5) 0.19783(5) 0.18482(5) 0.02103(18) 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 C1 0.0161(12) 0.0208(14) 0.0185(12) 0.0029(10) 0.0061(10) 0.0033(10) C2 0.0206(14) 0.0243(15) 0.0240(14) -0.0001(11) 0.0024(11) -0.0021(11) C3 0.0201(13) 0.0395(17) 0.0201(13) -0.0018(12) 0.0015(11) -0.0008(13) C4 0.0188(13) 0.0352(17) 0.0240(13) 0.0123(12) 0.0070(11) 0.0049(12) C5 0.0203(13) 0.0212(15) 0.0296(14) 0.0064(11) 0.0095(12) 0.0000(11) C6 0.0206(13) 0.0220(14) 0.0182(12) -0.0007(10) 0.0075(10) -0.0002(11) C7 0.0176(12) 0.0164(13) 0.0163(12) 0.0015(10) 0.0033(10) 0.0013(10) C8 0.0198(13) 0.0210(14) 0.0203(13) 0.0012(11) 0.0069(11) -0.0015(11) C9 0.0251(14) 0.0236(14) 0.0175(12) -0.0019(11) 0.0042(11) 0.0024(11) C10 0.0205(13) 0.0174(13) 0.0242(13) 0.0000(11) -0.0019(11) -0.0015(11) C11 0.0162(13) 0.0217(14) 0.0265(13) 0.0030(11) 0.0053(11) -0.0019(11) C12 0.0204(13) 0.0188(13) 0.0210(13) 0.0029(10) 0.0071(11) 0.0009(11) C13 0.0138(12) 0.0181(13) 0.0186(12) -0.0016(10) 0.0019(10) -0.0017(10) C14 0.0178(13) 0.0247(14) 0.0194(13) 0.0020(11) 0.0055(11) -0.0006(11) C15 0.0195(13) 0.0218(14) 0.0262(14) 0.0032(11) 0.0030(11) -0.0013(11) C16 0.0196(13) 0.0203(14) 0.0264(14) -0.0031(11) 0.0001(11) 0.0016(11) C17 0.0263(14) 0.0294(16) 0.0215(13) -0.0012(11) 0.0085(11) 0.0043(12) C18 0.0224(14) 0.0238(15) 0.0204(13) 0.0027(11) 0.0056(11) 0.0011(11) C19 0.0164(12) 0.0209(14) 0.0180(12) 0.0000(10) 0.0047(10) -0.0036(10) C20 0.0180(13) 0.0212(14) 0.0240(13) -0.0035(11) 0.0044(11) -0.0028(11) C21 0.0190(13) 0.0317(16) 0.0194(13) -0.0023(11) 0.0034(11) 0.0031(12) O1 0.0370(11) 0.0281(11) 0.0193(9) -0.0014(8) 0.0117(8) -0.0005(9) O2 0.0234(9) 0.0301(11) 0.0245(9) -0.0008(8) 0.0069(8) 0.0065(8) O3 0.0276(10) 0.0300(12) 0.0399(11) 0.0025(9) -0.0039(9) -0.0083(9) P1 0.0158(3) 0.0172(4) 0.0168(3) 0.0006(3) 0.0042(3) -0.0012(3) S1 0.0187(4) 0.0264(4) 0.0284(4) 0.0080(3) 0.0050(3) -0.0002(3) S2 0.0191(3) 0.0230(4) 0.0195(3) -0.0002(3) 0.0032(3) -0.0002(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 C1 C6 1.388(3) . ? C1 C2 1.398(3) . ? C1 P1 1.795(2) . ? C2 C3 1.378(4) . ? C3 C4 1.386(4) . ? C4 C5 1.383(4) . ? C5 C6 1.389(3) . ? C7 C8 1.394(3) . ? C7 C12 1.400(3) . ? C7 P1 1.792(2) . ? C8 C9 1.387(3) . ? C9 C10 1.389(4) . ? C10 C11 1.394(4) . ? C11 C12 1.386(3) . ? C13 C18 1.392(3) . ? C13 C14 1.402(3) . ? C13 P1 1.794(2) . ? C14 C15 1.387(4) . ? C15 C16 1.379(4) . ? C16 C17 1.377(4) . ? C17 C18 1.384(4) . ? C19 C20 1.527(3) . ? C19 P1 1.805(2) . ? C20 C21 1.525(4) . ? C21 S1 1.820(3) . ? O1 S2 1.4507(19) . ? O2 S2 1.4442(18) . ? O3 S2 1.4484(19) . ? S1 S2 2.1117(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 C6 C1 C2 120.0(2) . . ? C6 C1 P1 121.02(18) . . ? C2 C1 P1 118.83(19) . . ? C3 C2 C1 119.5(2) . . ? C2 C3 C4 120.3(2) . . ? C5 C4 C3 120.6(2) . . ? C4 C5 C6 119.4(2) . . ? C1 C6 C5 120.2(2) . . ? C8 C7 C12 120.0(2) . . ? C8 C7 P1 121.99(19) . . ? C12 C7 P1 118.01(18) . . ? C9 C8 C7 119.6(2) . . ? C8 C9 C10 120.4(2) . . ? C9 C10 C11 120.2(2) . . ? C12 C11 C10 119.7(2) . . ? C11 C12 C7 120.1(2) . . ? C18 C13 C14 119.8(2) . . ? C18 C13 P1 122.25(19) . . ? C14 C13 P1 117.96(18) . . ? C15 C14 C13 119.5(2) . . ? C16 C15 C14 120.2(2) . . ? C17 C16 C15 120.4(2) . . ? C16 C17 C18 120.4(2) . . ? C17 C18 C13 119.7(2) . . ? C20 C19 P1 115.39(17) . . ? C21 C20 C19 111.2(2) . . ? C20 C21 S1 114.77(18) . . ? C7 P1 C1 107.97(11) . . ? C7 P1 C13 111.12(11) . . ? C1 P1 C13 110.13(11) . . ? C7 P1 C19 111.92(11) . . ? C1 P1 C19 108.79(11) . . ? C13 P1 C19 106.90(11) . . ? C21 S1 S2 99.77(9) . . ? O2 S2 O3 115.11(12) . . ? O2 S2 O1 113.38(11) . . ? O3 S2 O1 113.15(12) . . ? O2 S2 S1 105.60(7) . . ? O3 S2 S1 101.20(8) . . ? O1 S2 S1 106.97(8) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.311 _refine_diff_density_min -0.444 _refine_diff_density_rms 0.067 # Attachment '03src0865.cif' data_03src0865 _database_code_depnum_ccdc_archive 'CCDC 620796' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H33 O3 P S2' _chemical_formula_weight 356.50 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' S S 0.1246 0.1234 '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/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 9.0500(3) _cell_length_b 14.3012(4) _cell_length_c 15.0732(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.326(2) _cell_angle_gamma 90.00 _cell_volume 1938.98(11) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.364 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9645 _exptl_absorpt_correction_T_max 0.9892 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 Nonius Kappa CCD Area detector' _diffrn_measurement_method '\f and \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23499 _diffrn_reflns_av_R_equivalents 0.0797 _diffrn_reflns_av_sigmaI/netI 0.0428 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3406 _reflns_number_gt 2663 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski and MInor, 1997)' _computing_data_reduction 'DENZO, COLLECT, MAXUS (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^)+(0.0654P)^2^+3.2275P] 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 0.0028(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3406 _refine_ls_number_parameters 194 _refine_ls_number_restraints 39 _refine_ls_R_factor_all 0.0775 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.1589 _refine_ls_wR_factor_gt 0.1487 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.007 _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 -0.31838(10) 0.32084(7) -0.13311(6) 0.0345(3) Uani 1 1 d . . . S1 S 0.21260(11) 0.26739(8) -0.02045(7) 0.0464(3) Uani 1 1 d . . . S2 S 0.19929(10) 0.33042(6) 0.10447(6) 0.0364(3) Uani 1 1 d . . . O1 O 0.0441(3) 0.3322(3) 0.11799(19) 0.0652(10) Uani 1 1 d . . . O2 O 0.2621(4) 0.42211(19) 0.0966(2) 0.0594(9) Uani 1 1 d . . . O3 O 0.2877(3) 0.26858(19) 0.16420(19) 0.0496(7) Uani 1 1 d . . . C1 C -0.3682(4) 0.3731(2) -0.0315(2) 0.0401(9) Uani 1 1 d D . . H1A H -0.3125 0.4324 -0.0208 0.048 Uiso 1 1 calc R . . H1B H -0.4755 0.3885 -0.0394 0.048 Uiso 1 1 calc R . . C2 C -0.3365(4) 0.3109(2) 0.04978(19) 0.0416(9) Uani 1 1 d D . . H2A H -0.4073 0.2579 0.0450 0.050 Uiso 1 1 calc R . . H2B H -0.2349 0.2849 0.0510 0.050 Uiso 1 1 calc R . . C3 C -0.3493(5) 0.3628(3) 0.1359(2) 0.0518(11) Uani 1 1 d D . . H3A H -0.2735 0.4130 0.1425 0.062 Uiso 1 1 calc R . . H3B H -0.4484 0.3927 0.1327 0.062 Uiso 1 1 calc R . . C4 C -0.3291(5) 0.3012(3) 0.2161(2) 0.0611(13) Uani 1 1 d D . . H4A H -0.4082 0.2541 0.2121 0.092 Uiso 1 1 calc R . . H4B H -0.3337 0.3390 0.2699 0.092 Uiso 1 1 calc R . . H4C H -0.2323 0.2701 0.2190 0.092 Uiso 1 1 calc R . . C5 C -0.4255(4) 0.2165(2) -0.1588(3) 0.0397(9) Uani 1 1 d D . . H5A H -0.5255 0.2271 -0.1399 0.048 Uiso 1 1 calc R . . H5B H -0.4385 0.2097 -0.2245 0.048 Uiso 1 1 calc R . . C6 C -0.3695(4) 0.1237(2) -0.1197(3) 0.0520(11) Uani 1 1 d D . . H6A H -0.2707 0.1103 -0.1391 0.062 Uiso 1 1 calc R . . H6B H -0.3577 0.1280 -0.0538 0.062 Uiso 1 1 calc R . . C7 C -0.4742(5) 0.0443(2) -0.1484(3) 0.0745(15) Uani 1 1 d DU . . H7A H -0.5742 0.0596 -0.1317 0.089 Uiso 1 1 calc R . . H7B H -0.4822 0.0385 -0.2142 0.089 Uiso 1 1 calc R . . C8 C -0.4262(7) -0.0473(3) -0.1078(4) 0.096(2) Uani 1 1 d DU . . H8A H -0.3262 -0.0623 -0.1227 0.144 Uiso 1 1 calc R . . H8B H -0.4957 -0.0962 -0.1312 0.144 Uiso 1 1 calc R . . H8C H -0.4252 -0.0436 -0.0428 0.144 Uiso 1 1 calc R . . C9 C -0.3580(4) 0.4002(3) -0.2249(2) 0.0425(9) Uani 1 1 d D . . H9A H -0.3087 0.4607 -0.2091 0.051 Uiso 1 1 calc R . . H9B H -0.3140 0.3749 -0.2772 0.051 Uiso 1 1 calc R . . C10 C -0.5220(4) 0.4180(3) -0.2515(3) 0.0780(17) Uani 1 1 d D . . H10A H -0.5727 0.3577 -0.2660 0.094 Uiso 1 1 calc R . . H10B H -0.5660 0.4459 -0.2003 0.094 Uiso 1 1 calc R . . C11 C -0.5488(7) 0.4826(4) -0.3309(4) 0.104(2) Uani 1 1 d DU . . H11A H -0.6348 0.5234 -0.3229 0.125 Uiso 1 1 calc R . . H11B H -0.4607 0.5232 -0.3330 0.125 Uiso 1 1 calc R . . C12 C -0.5784(16) 0.4323(7) -0.4175(4) 0.220(5) Uani 1 1 d DU . . H12A H -0.5852 0.3650 -0.4063 0.330 Uiso 1 1 calc R . . H12B H -0.4971 0.4443 -0.4539 0.330 Uiso 1 1 calc R . . H12C H -0.6722 0.4544 -0.4492 0.330 Uiso 1 1 calc R . . C13 C -0.1225(4) 0.2956(3) -0.1217(3) 0.0396(9) Uani 1 1 d . . . H13A H -0.1010 0.2460 -0.0763 0.048 Uiso 1 1 calc R . . H13B H -0.0951 0.2714 -0.1792 0.048 Uiso 1 1 calc R . . C14 C -0.0266(4) 0.3815(3) -0.0945(3) 0.0419(9) Uani 1 1 d . . . H14A H -0.0540 0.4330 -0.1370 0.050 Uiso 1 1 calc R . . H14B H -0.0474 0.4024 -0.0345 0.050 Uiso 1 1 calc R . . C15 C 0.1396(4) 0.3610(3) -0.0928(3) 0.0470(10) Uani 1 1 d . . . H15A H 0.1951 0.4188 -0.0746 0.056 Uiso 1 1 calc R . . H15B H 0.1602 0.3460 -0.1544 0.056 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 0.0338(5) 0.0372(5) 0.0338(6) -0.0035(4) 0.0093(4) -0.0026(4) S1 0.0387(6) 0.0547(7) 0.0458(6) -0.0132(5) 0.0042(4) 0.0031(4) S2 0.0344(5) 0.0411(5) 0.0335(5) 0.0023(4) 0.0020(4) 0.0023(4) O1 0.0374(16) 0.122(3) 0.0377(17) 0.0094(17) 0.0103(13) 0.0155(17) O2 0.087(2) 0.0367(16) 0.0525(18) 0.0012(13) -0.0024(16) -0.0071(15) O3 0.0437(16) 0.0513(17) 0.0515(18) 0.0145(13) -0.0045(13) 0.0041(13) C1 0.042(2) 0.041(2) 0.039(2) -0.0062(17) 0.0114(17) -0.0021(17) C2 0.034(2) 0.057(2) 0.035(2) -0.0033(18) 0.0079(16) -0.0038(17) C3 0.043(2) 0.073(3) 0.041(2) -0.008(2) 0.0119(18) -0.006(2) C4 0.053(3) 0.096(4) 0.035(2) -0.001(2) 0.008(2) 0.006(3) C5 0.039(2) 0.041(2) 0.041(2) -0.0047(17) 0.0112(17) -0.0066(16) C6 0.066(3) 0.041(2) 0.052(3) -0.0014(19) 0.019(2) 0.003(2) C7 0.112(4) 0.046(3) 0.070(3) -0.006(2) 0.028(3) -0.021(3) C8 0.159(6) 0.045(3) 0.097(4) 0.002(3) 0.067(4) 0.000(3) C9 0.053(2) 0.039(2) 0.037(2) -0.0039(17) 0.0126(18) -0.0020(18) C10 0.064(3) 0.064(3) 0.098(4) 0.025(3) -0.027(3) -0.017(3) C11 0.116(5) 0.079(4) 0.109(5) 0.027(4) -0.026(4) 0.011(4) C12 0.270(10) 0.212(9) 0.166(8) 0.034(7) -0.034(7) -0.051(8) C13 0.034(2) 0.051(2) 0.035(2) -0.0053(17) 0.0109(16) -0.0050(17) C14 0.039(2) 0.051(2) 0.035(2) 0.0042(17) -0.0008(16) -0.0075(18) C15 0.039(2) 0.071(3) 0.031(2) 0.0009(19) 0.0057(17) -0.013(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 P1 C9 1.796(4) . ? P1 C5 1.798(3) . ? P1 C13 1.799(4) . ? P1 C1 1.805(3) . ? S1 C15 1.805(4) . ? S1 S2 2.1030(14) . ? S2 O2 1.439(3) . ? S2 O3 1.440(3) . ? S2 O1 1.441(3) . ? C1 C2 1.516(3) . ? C2 C3 1.511(4) . ? C3 C4 1.490(4) . ? C5 C6 1.517(3) . ? C6 C7 1.511(4) . ? C7 C8 1.489(4) . ? C9 C10 1.516(3) . ? C10 C11 1.510(4) . ? C11 C12 1.489(4) . ? C13 C14 1.533(5) . ? C14 C15 1.530(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 C9 P1 C5 107.56(17) . . ? C9 P1 C13 108.13(18) . . ? C5 P1 C13 110.89(17) . . ? C9 P1 C1 110.16(16) . . ? C5 P1 C1 110.32(18) . . ? C13 P1 C1 109.73(18) . . ? C15 S1 S2 99.78(14) . . ? O2 S2 O3 114.45(18) . . ? O2 S2 O1 113.3(2) . . ? O3 S2 O1 113.90(18) . . ? O2 S2 S1 104.75(14) . . ? O3 S2 S1 102.34(13) . . ? O1 S2 S1 106.67(14) . . ? C2 C1 P1 113.6(2) . . ? C3 C2 C1 112.4(2) . . ? C4 C3 C2 113.1(3) . . ? C6 C5 P1 119.6(2) . . ? C7 C6 C5 112.0(2) . . ? C8 C7 C6 113.5(3) . . ? C10 C9 P1 114.6(3) . . ? C11 C10 C9 112.3(2) . . ? C12 C11 C10 113.3(3) . . ? C14 C13 P1 112.8(3) . . ? C15 C14 C13 112.2(3) . . ? C14 C15 S1 116.4(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.078 _refine_diff_density_min -0.633 _refine_diff_density_rms 0.067