# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 1145/225 data_HMASPS _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H30 N2 O5 S' _chemical_formula_weight 458.56 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' 'N' 'N' 0.0061 0.0033 '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' '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 P2(1)/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 9.929(2) _cell_length_b 19.549(4) _cell_length_c 12.100(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.11(3) _cell_angle_gamma 90.00 _cell_volume 2335.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.176 _exptl_absorpt_correction_type 'abscor' _exptl_absorpt_correction_T_min 0.801 _exptl_absorpt_correction_T_max 1.174 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotation anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'IP Rigaku' _diffrn_measurement_method 'IP' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3581 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0664 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3581 _reflns_number_gt 3349 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAXIS Rigaku' _computing_cell_refinement 'BIOTEX Rigaku' _computing_data_reduction 'BIOTEX Rigaku' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Slemens SHELXTL' _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^)+(0.1204P)^2^+1.0177P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom and difmap' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.029(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3581 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0811 _refine_ls_R_factor_gt 0.0776 _refine_ls_wR_factor_ref 0.2347 _refine_ls_wR_factor_gt 0.2303 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.051 _refine_ls_shift/su_mean 0.008 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 S1 S 0.77664(3) 0.040901(16) 0.71866(3) 0.06027(10) Uani 1 1 d . . . N1 N 0.13370(11) -0.18792(6) 0.82859(11) 0.0670(3) Uani 1 1 d . . . N2 N 1.10402(11) -0.21225(6) 0.50785(9) 0.0642(3) Uani 1 1 d . . . O1 O 0.03809(13) -0.12132(6) 1.03144(9) 0.0890(4) Uani 1 1 d . . . H1A H 0.0808 -0.1144 1.0922 0.133 Uiso 1 1 calc R . . O2 O 0.83106(10) 0.10627(5) 0.75759(10) 0.0800(3) Uani 1 1 d . . . O3 O 0.81559(12) -0.01347(6) 0.79526(12) 0.1024(4) Uani 1 1 d . . . O4 O 0.80389(11) 0.02630(7) 0.60675(10) 0.0905(4) Uani 1 1 d . . . O5 O -0.24573(13) -0.10629(7) 0.96511(11) 0.1020(4) Uani 1 1 d . . . C1 C 0.25769(14) -0.19190(7) 0.79253(12) 0.0608(4) Uani 1 1 d . . . C2 C 0.31991(14) -0.25501(7) 0.77469(12) 0.0681(4) Uani 1 1 d . . . H2A H 0.2747 -0.2951 0.7897 0.082 Uiso 1 1 calc R . . C3 C 0.44216(16) -0.25984(9) 0.73681(13) 0.0787(5) Uani 1 1 d . . . H3A H 0.4777 -0.3029 0.7252 0.094 Uiso 1 1 calc R . . C4 C 0.51619(16) -0.20277(10) 0.71480(14) 0.0855(5) Uani 1 1 d . . . C5 C 0.45921(16) -0.13945(9) 0.73221(14) 0.0862(5) Uani 1 1 d . . . H5A H 0.5067 -0.1001 0.7175 0.103 Uiso 1 1 calc R . . C6 C 0.33474(16) -0.13334(8) 0.77050(15) 0.0815(5) Uani 1 1 d . . . H6A H 0.3002 -0.0900 0.7822 0.098 Uiso 1 1 calc R . . C7 C 0.6627(3) -0.22182(10) 0.66675(16) 0.1424(9) Uani 1 1 d . . . H7A H 0.6932 -0.2660 0.6551 0.171 Uiso 1 1 calc R . . C8 C 0.7191(3) -0.17415(9) 0.65050(15) 0.1360(9) Uani 1 1 d . . . H8A H 0.6908 -0.1299 0.6645 0.163 Uiso 1 1 calc R . . C9 C 0.86253(18) -0.19447(11) 0.59688(13) 0.0943(6) Uani 1 1 d . . . C10 C 0.91226(18) -0.25976(11) 0.57814(14) 0.0982(6) Uani 1 1 d . . . H10A H 0.8639 -0.2981 0.5967 0.118 Uiso 1 1 calc R . . C11 C 1.03423(16) -0.26793(9) 0.53173(13) 0.0777(5) Uani 1 1 d . . . H11A H 1.0664 -0.3114 0.5176 0.093 Uiso 1 1 calc R . . C12 C 1.05394(16) -0.14964(8) 0.52601(12) 0.0720(5) Uani 1 1 d . . . H12A H 1.1027 -0.1114 0.5079 0.086 Uiso 1 1 calc R . . C13 C 0.93645(17) -0.14053(10) 0.56917(14) 0.0856(6) Uani 1 1 d . . . H13A H 0.9055 -0.0964 0.5801 0.103 Uiso 1 1 calc R . . C14 C 1.23496(15) -0.21826(9) 0.46323(14) 0.0814(5) Uani 1 1 d . . . H14A H 1.2570 -0.2657 0.4556 0.122 Uiso 1 1 calc R . . H14B H 1.3037 -0.1965 0.5130 0.122 Uiso 1 1 calc R . . H14C H 1.2300 -0.1965 0.3918 0.122 Uiso 1 1 calc R . . C15 C 0.06653(15) -0.12230(7) 0.83938(12) 0.0687(4) Uani 1 1 d . . . H15A H -0.0306 -0.1296 0.8289 0.082 Uiso 1 1 calc R . . H15B H 0.0896 -0.0924 0.7802 0.082 Uiso 1 1 calc R . . C16 C 0.10147(17) -0.08670(8) 0.94813(13) 0.0758(5) Uani 1 1 d . . . H16A H 0.1989 -0.0866 0.9670 0.091 Uiso 1 1 calc R . . H16B H 0.0706 -0.0396 0.9427 0.091 Uiso 1 1 calc R . . C17 C 0.06351(15) -0.24873(8) 0.86042(14) 0.0765(5) Uani 1 1 d . . . H17A H 0.1181 -0.2883 0.8504 0.115 Uiso 1 1 calc R . . H17B H -0.0214 -0.2528 0.8149 0.115 Uiso 1 1 calc R . . H17C H 0.0474 -0.2453 0.9371 0.115 Uiso 1 1 calc R . . C18 C 0.31751(14) 0.05503(7) 0.71315(14) 0.0688(4) Uani 1 1 d . . . C19 C 0.39869(16) 0.05124(8) 0.81189(14) 0.0762(5) Uani 1 1 d . . . H19A H 0.3596 0.0513 0.8784 0.091 Uiso 1 1 calc R . . C20 C 0.53877(16) 0.04724(8) 0.81381(13) 0.0740(5) Uani 1 1 d . . . H20A H 0.5923 0.0436 0.8815 0.089 Uiso 1 1 calc R . . C21 C 0.59914(14) 0.04863(6) 0.71610(12) 0.0582(4) Uani 1 1 d . . . C22 C 0.51790(15) 0.05460(7) 0.61658(13) 0.0673(4) Uani 1 1 d . . . H22A H 0.5568 0.0568 0.5501 0.081 Uiso 1 1 calc R . . C23 C 0.37833(16) 0.05728(8) 0.61586(15) 0.0785(5) Uani 1 1 d . . . H23A H 0.3245 0.0607 0.5483 0.094 Uiso 1 1 calc R . . C24 C 0.16546(17) 0.05494(9) 0.7109(2) 0.0977(7) Uani 1 1 d . . . H24B H 0.1251 0.0581 0.6354 0.147 Uiso 1 1 calc R . . H24C H 0.1376 0.0933 0.7524 0.147 Uiso 1 1 calc R . . H24D H 0.1368 0.0133 0.7434 0.147 Uiso 1 1 calc R . . H5WB H -0.245(2) -0.0789(11) 0.9117(18) 0.131(7) Uiso 1 1 d . . . H5WA H -0.149(3) -0.1055(13) 1.018(2) 0.168(9) Uiso 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 S1 0.05743(17) 0.04938(16) 0.0735(2) 0.00080(14) 0.00480(17) -0.00267(13) N1 0.0589(6) 0.0550(6) 0.0900(7) 0.0013(5) 0.0219(6) 0.0058(5) N2 0.0589(6) 0.0724(7) 0.0617(6) 0.0036(5) 0.0087(5) 0.0052(5) O1 0.1039(8) 0.0947(7) 0.0674(6) -0.0008(6) 0.0052(6) -0.0129(6) O2 0.0745(6) 0.0602(5) 0.1021(7) -0.0071(5) -0.0058(6) -0.0158(4) O3 0.0787(7) 0.0818(6) 0.1466(9) 0.0521(6) 0.0123(7) 0.0150(5) O4 0.0721(6) 0.1166(8) 0.0851(6) -0.0236(6) 0.0196(5) -0.0067(6) O5 0.1003(8) 0.1102(9) 0.0996(8) 0.0104(7) 0.0294(7) -0.0126(7) C1 0.0597(7) 0.0530(6) 0.0701(7) 0.0009(6) 0.0089(6) 0.0039(5) C2 0.0720(8) 0.0541(7) 0.0795(8) -0.0023(6) 0.0140(7) 0.0102(6) C3 0.0757(8) 0.0781(9) 0.0821(9) -0.0061(8) 0.0069(8) 0.0183(7) C4 0.0589(7) 0.1237(13) 0.0741(9) -0.0129(9) 0.0089(7) 0.0193(8) C5 0.0764(8) 0.0909(10) 0.0948(10) 0.0014(9) 0.0249(8) -0.0213(8) C6 0.0865(9) 0.0539(7) 0.1090(11) -0.0024(8) 0.0335(8) -0.0015(7) C7 0.245(2) 0.0674(10) 0.0959(11) 0.0166(9) -0.0711(13) -0.0361(12) C8 0.251(3) 0.0547(9) 0.0864(11) -0.0081(8) -0.0560(14) 0.0120(12) C9 0.0767(9) 0.1455(15) 0.0597(8) -0.0129(9) 0.0029(8) 0.0325(9) C10 0.0843(9) 0.1370(13) 0.0718(9) 0.0198(9) 0.0011(8) -0.0481(9) C11 0.0833(9) 0.0745(9) 0.0754(9) 0.0056(7) 0.0089(8) -0.0076(8) C12 0.0723(8) 0.0700(8) 0.0732(8) 0.0002(7) 0.0056(7) 0.0076(7) C13 0.0759(9) 0.1041(12) 0.0773(9) -0.0035(9) 0.0095(8) 0.0178(8) C14 0.0684(8) 0.0946(11) 0.0839(9) 0.0080(8) 0.0204(8) 0.0103(8) C15 0.0691(7) 0.0644(7) 0.0732(8) -0.0006(7) 0.0099(7) 0.0198(6) C16 0.0812(9) 0.0674(8) 0.0792(9) -0.0035(7) 0.0104(8) 0.0049(7) C17 0.0715(8) 0.0733(8) 0.0857(9) 0.0061(8) 0.0138(8) -0.0068(7) C18 0.0606(7) 0.0465(6) 0.1005(10) 0.0023(7) 0.0134(7) 0.0021(6) C19 0.0734(8) 0.0728(8) 0.0854(9) -0.0079(8) 0.0223(8) -0.0014(7) C20 0.0713(9) 0.0777(9) 0.0720(8) -0.0080(7) 0.0036(8) -0.0048(7) C21 0.0619(7) 0.0427(6) 0.0700(7) -0.0056(5) 0.0070(6) -0.0027(5) C22 0.0666(8) 0.0670(8) 0.0680(8) 0.0027(7) 0.0053(7) 0.0021(6) C23 0.0636(8) 0.0732(8) 0.0951(10) 0.0067(8) -0.0088(9) 0.0051(7) C24 0.0664(9) 0.0695(9) 0.1577(17) 0.0170(10) 0.0146(11) 0.0067(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 S1 O3 1.4360(13) . ? S1 O4 1.4374(13) . ? S1 O2 1.4466(11) . ? S1 C21 1.7659(15) . ? N1 C1 1.3515(19) . ? N1 C17 1.451(2) . ? N1 C15 1.4581(18) . ? N2 C11 1.338(2) . ? N2 C12 1.3478(19) . ? N2 C14 1.465(2) . ? O1 C16 1.416(2) . ? C1 C2 1.4067(19) . ? C1 C6 1.418(2) . ? C2 C3 1.346(2) . ? C3 C4 1.377(3) . ? C4 C5 1.386(3) . ? C4 C7 1.665(3) . ? C5 C6 1.370(2) . ? C7 C8 1.115(3) . ? C8 C9 1.674(3) . ? C9 C13 1.347(3) . ? C9 C10 1.396(3) . ? C10 C11 1.397(2) . ? C12 C13 1.340(2) . ? C15 C16 1.496(2) . ? C18 C19 1.370(2) . ? C18 C23 1.380(2) . ? C18 C24 1.507(2) . ? C19 C20 1.391(2) . ? C20 C21 1.382(2) . ? C21 C22 1.381(2) . ? C22 C23 1.386(2) . ? 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 O3 S1 O4 113.35(8) . . ? O3 S1 O2 112.21(7) . . ? O4 S1 O2 112.39(7) . . ? O3 S1 C21 105.92(7) . . ? O4 S1 C21 106.74(7) . . ? O2 S1 C21 105.52(6) . . ? C1 N1 C17 121.23(11) . . ? C1 N1 C15 121.38(11) . . ? C17 N1 C15 117.38(12) . . ? C11 N2 C12 119.66(13) . . ? C11 N2 C14 120.97(13) . . ? C12 N2 C14 119.36(13) . . ? N1 C1 C2 122.01(12) . . ? N1 C1 C6 122.86(13) . . ? C2 C1 C6 115.13(13) . . ? C3 C2 C1 122.72(14) . . ? C2 C3 C4 121.89(16) . . ? C3 C4 C5 117.31(15) . . ? C3 C4 C7 112.98(16) . . ? C5 C4 C7 129.68(16) . . ? C6 C5 C4 121.77(16) . . ? C5 C6 C1 121.15(15) . . ? C8 C7 C4 110.4(2) . . ? C7 C8 C9 109.5(2) . . ? C13 C9 C10 117.63(17) . . ? C13 C9 C8 114.78(17) . . ? C10 C9 C8 127.60(17) . . ? C9 C10 C11 120.44(18) . . ? N2 C11 C10 118.99(16) . . ? C13 C12 N2 122.41(15) . . ? C12 C13 C9 120.86(18) . . ? N1 C15 C16 115.00(12) . . ? O1 C16 C15 108.94(13) . . ? C19 C18 C23 118.38(14) . . ? C19 C18 C24 120.73(17) . . ? C23 C18 C24 120.87(16) . . ? C18 C19 C20 120.80(16) . . ? C21 C20 C19 120.58(15) . . ? C22 C21 C20 118.78(14) . . ? C22 C21 S1 120.78(12) . . ? C20 C21 S1 120.43(11) . . ? C21 C22 C23 119.97(15) . . ? C18 C23 C22 121.44(15) . . ? _diffrn_measured_fraction_theta_max 0.869 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.869 _refine_diff_density_max 0.466 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.051 #===END data_HEASPS _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H30 N2 O4 S' _chemical_formula_weight 454.57 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' 'N' 'N' 0.0061 0.0033 '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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4237(8) _cell_length_b 9.6976(8) _cell_length_c 13.2841(9) _cell_angle_alpha 86.655(6) _cell_angle_beta 74.064(5) _cell_angle_gamma 85.891(7) _cell_volume 1163.40(16) _cell_formula_units_Z 2 _cell_measurement_temperature 568(2) _cell_measurement_reflns_used 50 _cell_measurement_theta_min 5 _cell_measurement_theta_max 12.5 _exptl_crystal_description Plate _exptl_crystal_colour Orange _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.173 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.948 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details 'Bruker Shelxtl' _exptl_special_details ; ? ; _diffrn_ambient_temperature 568(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 P4' _diffrn_measurement_method /q\2/q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2 _diffrn_reflns_number 4929 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4111 _reflns_number_gt 2954 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0982P)^2^+0.7029P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4111 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0842 _refine_ls_R_factor_gt 0.0573 _refine_ls_wR_factor_ref 0.1832 _refine_ls_wR_factor_gt 0.1575 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _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 S1 S 0.32634(9) 0.06253(8) 0.22868(6) 0.0473(3) Uani 1 1 d . . . N1 N -0.1806(3) 0.9885(3) 1.1997(2) 0.0502(6) Uani 1 1 d . . . N2 N 0.3098(3) 0.3001(3) 0.5744(2) 0.0580(7) Uani 1 1 d . . . O1 O 0.3955(3) 0.0722(3) 0.3122(2) 0.0685(7) Uani 1 1 d . . . O2 O 0.1722(3) 0.1119(2) 0.2564(2) 0.0641(7) Uani 1 1 d . . . O3 O 0.4105(3) 0.1213(2) 0.12936(18) 0.0649(7) Uani 1 1 d . . . O4 O 0.0267(4) 0.2420(5) 0.4401(3) 0.1276(14) Uani 1 1 d . . . H4A H 0.0684 0.2042 0.3853 0.191 Uiso 1 1 calc R . . C21 C 0.2555(4) -0.3429(3) 0.2803(3) 0.0594(9) Uani 1 1 d . . . H21A H 0.2082 -0.3997 0.3366 0.071 Uiso 1 1 calc R . . C22 C 0.2560(3) -0.2031(3) 0.2938(2) 0.0501(8) Uani 1 1 d . . . H22A H 0.2103 -0.1666 0.3587 0.060 Uiso 1 1 calc R . . C23 C 0.3247(3) -0.1174(3) 0.2105(2) 0.0413(7) Uani 1 1 d . . . C24 C 0.3927(3) -0.1724(3) 0.1133(2) 0.0456(7) Uani 1 1 d . . . H24A H 0.4389 -0.1155 0.0567 0.055 Uiso 1 1 calc R . . C25 C 0.3904(4) -0.3139(3) 0.1023(3) 0.0537(8) Uani 1 1 d . . . H25A H 0.4353 -0.3507 0.0373 0.064 Uiso 1 1 calc R . . C1 C -0.2358(4) 1.0833(4) 1.2874(3) 0.0669(10) Uani 1 1 d . . . H1B H -0.1721 1.0728 1.3329 0.100 Uiso 1 1 calc R . . H1C H -0.3342 1.0613 1.3260 0.100 Uiso 1 1 calc R . . H1D H -0.2370 1.1771 1.2600 0.100 Uiso 1 1 calc R . . C2 C -0.0568(4) 0.9080(4) 1.1937(3) 0.0548(8) Uani 1 1 d . . . H2B H -0.0075 0.9118 1.2452 0.066 Uiso 1 1 calc R . . C3 C -0.0022(3) 0.8210(3) 1.1135(3) 0.0530(8) Uani 1 1 d . . . H3B H 0.0827 0.7650 1.1117 0.064 Uiso 1 1 calc R . . C4 C -0.0718(3) 0.8147(3) 1.0341(2) 0.0448(7) Uani 1 1 d . . . C5 C -0.2003(4) 0.9000(3) 1.0435(3) 0.0535(8) Uani 1 1 d . . . H5A H -0.2513 0.8992 0.9927 0.064 Uiso 1 1 calc R . . C6 C -0.2524(4) 0.9847(3) 1.1261(3) 0.0543(8) Uani 1 1 d . . . H6A H -0.3385 1.0402 1.1311 0.065 Uiso 1 1 calc R . . C7 C -0.0191(3) 0.7291(3) 0.9437(2) 0.0492(7) Uani 1 1 d . . . H7A H -0.0716 0.7386 0.8936 0.059 Uiso 1 1 calc R . . C8 C 0.0978(4) 0.6378(3) 0.9255(2) 0.0502(8) Uani 1 1 d . . . H8A H 0.1502 0.6283 0.9757 0.060 Uiso 1 1 calc R . . C9 C 0.1506(3) 0.5524(3) 0.8351(2) 0.0466(7) Uani 1 1 d . . . C10 C 0.2747(3) 0.4611(3) 0.8253(2) 0.0513(8) Uani 1 1 d . . . H10A H 0.3224 0.4553 0.8782 0.062 Uiso 1 1 calc R . . C11 C 0.3291(4) 0.3794(3) 0.7403(2) 0.0523(8) Uani 1 1 d . . . H11A H 0.4132 0.3213 0.7366 0.063 Uiso 1 1 calc R . . C12 C 0.2605(3) 0.3822(3) 0.6600(2) 0.0489(7) Uani 1 1 d . . . C13 C 0.1356(4) 0.4750(4) 0.6686(3) 0.0570(8) Uani 1 1 d . . . H13A H 0.0873 0.4807 0.6159 0.068 Uiso 1 1 calc R . . C14 C 0.0846(4) 0.5566(4) 0.7533(3) 0.0555(8) Uani 1 1 d . . . H14A H 0.0026 0.6172 0.7561 0.067 Uiso 1 1 calc R . . C15 C 0.4526(4) 0.2191(4) 0.5544(3) 0.0637(9) Uani 1 1 d . . . H15A H 0.4497 0.1407 0.5130 0.076 Uiso 1 1 calc R . . H15B H 0.4680 0.1836 0.6206 0.076 Uiso 1 1 calc R . . C16 C 0.5797(4) 0.3045(5) 0.4974(3) 0.0776(11) Uani 1 1 d . . . H16A H 0.6704 0.2483 0.4856 0.116 Uiso 1 1 calc R . . H16B H 0.5843 0.3810 0.5389 0.116 Uiso 1 1 calc R . . H16C H 0.5656 0.3387 0.4313 0.116 Uiso 1 1 calc R . . C17 C 0.2401(4) 0.3106(4) 0.4889(3) 0.0662(10) Uani 1 1 d . . . H17A H 0.3124 0.2848 0.4243 0.079 Uiso 1 1 calc R . . H17B H 0.2045 0.4056 0.4797 0.079 Uiso 1 1 calc R . . C18 C 0.1099(5) 0.2152(6) 0.5116(3) 0.0920(16) Uani 1 1 d . . . H18A H 0.1478 0.1194 0.5079 0.110 Uiso 1 1 calc R . . H18B H 0.0472 0.2292 0.5819 0.110 Uiso 1 1 calc R . . C19 C 0.3292(5) -0.5547(4) 0.1717(4) 0.0866(14) Uani 1 1 d . . . H19A H 0.3809 -0.5756 0.1008 0.130 Uiso 1 1 calc R . . H19B H 0.2303 -0.5847 0.1875 0.130 Uiso 1 1 calc R . . H19C H 0.3798 -0.6017 0.2186 0.130 Uiso 1 1 calc R . . C20 C 0.3240(4) -0.4011(3) 0.1844(3) 0.0571(9) 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 S1 0.0517(5) 0.0395(4) 0.0531(5) -0.0093(3) -0.0181(4) 0.0039(3) N1 0.0471(15) 0.0478(15) 0.0535(15) -0.0044(12) -0.0093(13) -0.0023(12) N2 0.0531(17) 0.0694(18) 0.0512(16) -0.0140(14) -0.0139(13) 0.0062(14) O1 0.0844(18) 0.0627(15) 0.0715(16) -0.0204(12) -0.0421(14) 0.0054(13) O2 0.0535(14) 0.0533(14) 0.0857(17) -0.0178(12) -0.0207(13) 0.0143(11) O3 0.0835(18) 0.0428(12) 0.0614(14) 0.0001(11) -0.0077(13) -0.0062(12) O4 0.097(3) 0.185(4) 0.111(3) -0.048(3) -0.051(2) 0.046(3) C21 0.054(2) 0.0482(18) 0.069(2) 0.0113(16) -0.0073(17) -0.0046(15) C22 0.0471(18) 0.0533(18) 0.0469(17) -0.0024(14) -0.0095(14) 0.0038(14) C23 0.0399(16) 0.0388(15) 0.0470(16) -0.0038(12) -0.0156(13) 0.0022(12) C24 0.0422(17) 0.0467(17) 0.0467(17) -0.0033(13) -0.0105(14) 0.0007(13) C25 0.0487(19) 0.0486(18) 0.063(2) -0.0175(15) -0.0131(16) 0.0054(15) C1 0.070(2) 0.062(2) 0.063(2) -0.0173(17) -0.0066(19) 0.0012(19) C2 0.0453(18) 0.064(2) 0.060(2) -0.0092(16) -0.0213(16) -0.0008(16) C3 0.0426(18) 0.0598(19) 0.0582(19) -0.0101(15) -0.0178(15) 0.0099(15) C4 0.0391(16) 0.0472(16) 0.0481(17) 0.0004(13) -0.0121(13) -0.0045(13) C5 0.0486(19) 0.060(2) 0.0552(19) -0.0063(15) -0.0209(15) 0.0042(15) C6 0.0469(18) 0.0573(19) 0.0563(19) -0.0005(15) -0.0135(16) 0.0089(15) C7 0.0456(18) 0.0543(18) 0.0481(17) -0.0064(14) -0.0129(14) 0.0002(15) C8 0.0482(18) 0.0563(19) 0.0470(17) -0.0020(14) -0.0146(15) -0.0017(15) C9 0.0413(17) 0.0515(17) 0.0456(17) -0.0012(13) -0.0092(14) -0.0032(14) C10 0.0466(18) 0.062(2) 0.0459(17) -0.0055(15) -0.0147(14) 0.0047(15) C11 0.0460(18) 0.0576(19) 0.0511(18) -0.0028(15) -0.0115(15) 0.0055(15) C12 0.0453(18) 0.0554(18) 0.0426(16) -0.0019(14) -0.0060(14) -0.0035(14) C13 0.055(2) 0.068(2) 0.0516(19) -0.0103(16) -0.0210(16) 0.0071(17) C14 0.0473(19) 0.062(2) 0.057(2) -0.0091(16) -0.0151(16) 0.0102(16) C15 0.068(2) 0.058(2) 0.061(2) -0.0122(16) -0.0125(18) 0.0121(18) C16 0.060(2) 0.097(3) 0.067(2) -0.010(2) -0.0032(19) 0.003(2) C17 0.075(3) 0.076(2) 0.0455(19) -0.0098(17) -0.0136(17) 0.009(2) C18 0.057(2) 0.174(5) 0.048(2) -0.024(3) -0.0171(19) -0.001(3) C19 0.073(3) 0.044(2) 0.134(4) -0.013(2) -0.012(3) -0.0001(19) C20 0.0428(18) 0.0417(17) 0.087(3) -0.0068(17) -0.0180(18) 0.0011(14) _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 S1 O1 1.443(2) . ? S1 O3 1.448(2) . ? S1 O2 1.449(2) . ? S1 C23 1.777(3) . ? N1 C6 1.336(4) . ? N1 C2 1.343(4) . ? N1 C1 1.482(4) . ? N2 C12 1.381(4) . ? N2 C17 1.455(4) . ? N2 C15 1.475(4) . ? O4 C18 1.390(5) . ? C21 C22 1.378(5) . ? C21 C20 1.392(5) . ? C22 C23 1.383(4) . ? C23 C24 1.393(4) . ? C24 C25 1.390(4) . ? C25 C20 1.375(5) . ? C2 C3 1.362(5) . ? C3 C4 1.392(4) . ? C4 C5 1.397(4) . ? C4 C7 1.451(4) . ? C5 C6 1.368(4) . ? C7 C8 1.339(4) . ? C8 C9 1.451(4) . ? C9 C14 1.391(4) . ? C9 C10 1.396(4) . ? C10 C11 1.376(4) . ? C11 C12 1.389(4) . ? C12 C13 1.412(4) . ? C13 C14 1.370(5) . ? C15 C16 1.505(6) . ? C17 C18 1.542(6) . ? C19 C20 1.504(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 O1 S1 O3 113.31(16) . . ? O1 S1 O2 113.20(15) . . ? O3 S1 O2 112.83(15) . . ? O1 S1 C23 105.53(14) . . ? O3 S1 C23 105.95(14) . . ? O2 S1 C23 105.09(14) . . ? C6 N1 C2 120.2(3) . . ? C6 N1 C1 120.2(3) . . ? C2 N1 C1 119.6(3) . . ? C12 N2 C17 121.6(3) . . ? C12 N2 C15 121.4(3) . . ? C17 N2 C15 115.9(3) . . ? C22 C21 C20 121.6(3) . . ? C21 C22 C23 119.8(3) . . ? C22 C23 C24 119.9(3) . . ? C22 C23 S1 119.6(2) . . ? C24 C23 S1 120.5(2) . . ? C25 C24 C23 118.8(3) . . ? C20 C25 C24 122.1(3) . . ? N1 C2 C3 121.1(3) . . ? C2 C3 C4 120.9(3) . . ? C3 C4 C5 116.1(3) . . ? C3 C4 C7 124.9(3) . . ? C5 C4 C7 119.0(3) . . ? C6 C5 C4 121.1(3) . . ? N1 C6 C5 120.6(3) . . ? C8 C7 C4 126.4(3) . . ? C7 C8 C9 126.4(3) . . ? C14 C9 C10 116.0(3) . . ? C14 C9 C8 123.3(3) . . ? C10 C9 C8 120.8(3) . . ? C11 C10 C9 122.5(3) . . ? C10 C11 C12 121.1(3) . . ? N2 C12 C11 122.9(3) . . ? N2 C12 C13 120.1(3) . . ? C11 C12 C13 117.0(3) . . ? C14 C13 C12 120.9(3) . . ? C13 C14 C9 122.5(3) . . ? N2 C15 C16 111.9(3) . . ? N2 C17 C18 110.7(3) . . ? O4 C18 C17 111.2(4) . . ? C25 C20 C21 117.7(3) . . ? C25 C20 C19 121.0(3) . . ? C21 C20 C19 121.3(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.705 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.052 #===END