Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Edward R. T. Tiekink' 'Grant A. Broker' _publ_contact_author_name 'Edward R. T. Tiekink' _publ_contact_author_address ; Department of Chemistry The University of Texas at San Antonio 6900 Nth Loop 1604 West San Antonio Texas 78249-0698 UNITED STATES OF AMERICA ; _publ_contact_author_email EDWARD.TIEKINK@UTSA.EDU _publ_requested_journal CrystEngComm _publ_section_title ; Co-crystal formation between 2,2'-dithiobenzoic acid and each of 4,4'bipyridine, trans-1,2-bis(4-pyridyl)ethene and 1,2-bis(4-pyridyl)ethane ; data_(HO2C)C6H4SSC6H4(CO2H).4,4'-bipyridine(1) _database_code_depnum_ccdc_archive 'CCDC 648103' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 S2, C10 H8 N2' _chemical_formula_sum 'C24 H18 N2 O4 S2' _chemical_formula_weight 462.52 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 P21/c 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 9.1441(18) _cell_length_b 13.157(3) _cell_length_c 17.564(4) _cell_angle_alpha 90 _cell_angle_beta 95.04(3) _cell_angle_gamma 90 _cell_volume 2104.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6696 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.460 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.289 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.789 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC12\K/SATURN724 _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% '< 1' _diffrn_reflns_number 33721 _diffrn_reflns_av_R_equivalents 0.061 _diffrn_reflns_av_sigmaI/netI 0.034 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.2 _diffrn_reflns_theta_max 26.5 _reflns_number_total 4366 _reflns_number_gt 4099 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) & DIAMOND (Crystal Impact, 2006)' _computing_publication_material SHELXL97 _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^)+(0.0342P)^2^+1.4641P] 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 4366 _refine_ls_number_parameters 295 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.050 _refine_ls_R_factor_gt 0.045 _refine_ls_wR_factor_ref 0.097 _refine_ls_wR_factor_gt 0.094 _refine_ls_goodness_of_fit_ref 1.13 _refine_ls_restrained_S_all 1.13 _refine_ls_shift/su_max <0.001 _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 -0.12692(5) 0.34943(4) 0.32808(3) 0.01857(13) Uani 1 1 d . . . S2 S -0.31684(5) 0.30571(4) 0.37367(3) 0.01858(13) Uani 1 1 d . . . O1 O 0.15671(16) 0.53225(12) 0.18889(9) 0.0323(4) Uani 1 1 d D . . H1O H 0.2363(16) 0.5037(19) 0.1812(16) 0.048 Uiso 1 1 d D . . O2 O 0.11992(14) 0.39628(10) 0.26144(8) 0.0213(3) Uani 1 1 d . . . O3 O -0.65781(15) 0.29764(12) 0.53707(8) 0.0259(3) Uani 1 1 d D . . H3O H -0.7338(16) 0.2637(16) 0.5242(14) 0.039 Uiso 1 1 d D . . O4 O -0.56356(16) 0.23810(11) 0.43270(8) 0.0268(3) Uani 1 1 d . . . N1 N 0.40546(17) 0.45635(13) 0.15422(10) 0.0220(4) Uani 1 1 d . . . N2 N 1.08367(19) 0.29069(14) 0.03087(10) 0.0250(4) Uani 1 1 d . . . C1 C 0.4596(2) 0.36501(16) 0.17421(12) 0.0241(4) Uani 1 1 d . . . H1 H 0.4046 0.3224 0.2048 0.029 Uiso 1 1 calc R . . C2 C 0.5919(2) 0.32955(15) 0.15254(12) 0.0215(4) Uani 1 1 d . . . H2 H 0.6273 0.2645 0.1689 0.026 Uiso 1 1 calc R . . C3 C 0.6732(2) 0.39012(15) 0.10636(10) 0.0172(4) Uani 1 1 d . . . C4 C 0.6172(2) 0.48559(15) 0.08659(11) 0.0196(4) Uani 1 1 d . . . H4 H 0.6696 0.5299 0.0560 0.023 Uiso 1 1 calc R . . C5 C 0.4848(2) 0.51583(15) 0.11166(11) 0.0210(4) Uani 1 1 d . . . H5 H 0.4485 0.5816 0.0981 0.025 Uiso 1 1 calc R . . C6 C 0.8150(2) 0.35433(15) 0.08003(11) 0.0191(4) Uani 1 1 d . . . C7 C 0.8639(2) 0.38953(16) 0.01193(11) 0.0224(4) Uani 1 1 d . . . H7 H 0.8061 0.4362 -0.0191 0.027 Uiso 1 1 calc R . . C8 C 0.9972(2) 0.35609(17) -0.01020(12) 0.0247(5) Uani 1 1 d . . . H8 H 1.0288 0.3808 -0.0569 0.030 Uiso 1 1 calc R . . C9 C 1.0353(2) 0.25594(18) 0.09573(12) 0.0273(5) Uani 1 1 d . . . H9 H 1.0950 0.2089 0.1254 0.033 Uiso 1 1 calc R . . C10 C 0.9037(2) 0.28467(16) 0.12192(12) 0.0236(4) Uani 1 1 d . . . H10 H 0.8739 0.2572 0.1681 0.028 Uiso 1 1 calc R . . C11 C 0.0793(2) 0.47734(15) 0.23339(11) 0.0192(4) Uani 1 1 d . . . C12 C -0.0655(2) 0.52332(14) 0.24572(10) 0.0171(4) Uani 1 1 d . . . C13 C -0.1696(2) 0.47132(14) 0.28548(10) 0.0163(4) Uani 1 1 d . . . C14 C -0.3062(2) 0.51671(15) 0.29136(11) 0.0184(4) Uani 1 1 d . . . H14 H -0.3778 0.4824 0.3178 0.022 Uiso 1 1 calc R . . C15 C -0.3385(2) 0.61072(15) 0.25921(11) 0.0192(4) Uani 1 1 d . . . H15 H -0.4330 0.6395 0.2629 0.023 Uiso 1 1 calc R . . C16 C -0.2356(2) 0.66369(15) 0.22173(11) 0.0198(4) Uani 1 1 d . . . H16 H -0.2577 0.7289 0.2005 0.024 Uiso 1 1 calc R . . C17 C -0.0998(2) 0.61962(15) 0.21588(10) 0.0184(4) Uani 1 1 d . . . H17 H -0.0279 0.6558 0.1909 0.022 Uiso 1 1 calc R . . C18 C -0.3147(2) 0.37448(14) 0.46227(10) 0.0169(4) Uani 1 1 d . . . C19 C -0.4302(2) 0.36177(14) 0.50921(11) 0.0163(4) Uani 1 1 d . . . C20 C -0.4287(2) 0.41719(15) 0.57692(11) 0.0201(4) Uani 1 1 d . . . H20 H -0.5063 0.4082 0.6089 0.024 Uiso 1 1 calc R . . C21 C -0.3172(2) 0.48484(16) 0.59877(11) 0.0223(4) Uani 1 1 d . . . H21 H -0.3179 0.5219 0.6452 0.027 Uiso 1 1 calc R . . C22 C -0.2049(2) 0.49767(16) 0.55196(12) 0.0230(4) Uani 1 1 d . . . H22 H -0.1277 0.5441 0.5663 0.028 Uiso 1 1 calc R . . C23 C -0.2035(2) 0.44353(15) 0.48439(11) 0.0210(4) Uani 1 1 d . . . H23 H -0.1258 0.4536 0.4527 0.025 Uiso 1 1 calc R . . C24 C -0.5561(2) 0.29282(14) 0.48845(11) 0.0188(4) 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 0.0195(3) 0.0176(2) 0.0197(2) 0.00149(18) 0.00818(19) 0.00242(19) S2 0.0205(3) 0.0185(2) 0.0177(2) -0.00153(18) 0.00736(19) -0.00242(19) O1 0.0209(8) 0.0351(9) 0.0437(10) 0.0139(7) 0.0191(7) 0.0057(7) O2 0.0191(7) 0.0206(7) 0.0247(7) 0.0004(6) 0.0056(6) 0.0026(6) O3 0.0181(8) 0.0342(9) 0.0268(8) -0.0031(6) 0.0094(6) -0.0078(6) O4 0.0251(8) 0.0279(8) 0.0285(8) -0.0089(6) 0.0085(6) -0.0073(6) N1 0.0159(9) 0.0239(9) 0.0266(9) -0.0029(7) 0.0050(7) -0.0025(7) N2 0.0193(9) 0.0345(10) 0.0218(9) -0.0037(8) 0.0057(7) 0.0040(7) C1 0.0226(11) 0.0222(10) 0.0286(11) -0.0005(9) 0.0087(9) -0.0051(8) C2 0.0200(10) 0.0196(10) 0.0249(10) -0.0025(8) 0.0024(8) -0.0006(8) C3 0.0143(9) 0.0227(10) 0.0142(9) -0.0052(8) -0.0002(7) -0.0012(8) C4 0.0177(10) 0.0237(10) 0.0176(9) 0.0009(8) 0.0037(8) -0.0014(8) C5 0.0182(10) 0.0230(10) 0.0220(10) 0.0004(8) 0.0030(8) 0.0005(8) C6 0.0155(9) 0.0217(10) 0.0202(10) -0.0056(8) 0.0028(8) -0.0024(8) C7 0.0194(10) 0.0301(11) 0.0179(10) -0.0011(8) 0.0022(8) 0.0025(8) C8 0.0219(11) 0.0343(12) 0.0188(10) -0.0015(9) 0.0063(8) 0.0003(9) C9 0.0230(11) 0.0371(12) 0.0219(11) -0.0007(9) 0.0021(9) 0.0076(9) C10 0.0230(11) 0.0292(11) 0.0188(10) -0.0017(8) 0.0034(8) 0.0029(9) C11 0.0178(10) 0.0227(10) 0.0176(9) -0.0019(8) 0.0039(8) -0.0028(8) C12 0.0167(9) 0.0195(9) 0.0153(9) -0.0031(7) 0.0026(7) -0.0006(7) C13 0.0201(10) 0.0163(9) 0.0128(9) -0.0026(7) 0.0030(7) 0.0000(7) C14 0.0182(10) 0.0218(10) 0.0162(9) -0.0016(8) 0.0074(8) -0.0007(8) C15 0.0189(10) 0.0204(10) 0.0184(9) -0.0032(8) 0.0029(8) 0.0046(8) C16 0.0243(11) 0.0170(9) 0.0185(10) -0.0012(8) 0.0030(8) 0.0004(8) C17 0.0193(10) 0.0214(10) 0.0148(9) -0.0017(8) 0.0036(7) -0.0045(8) C18 0.0178(10) 0.0179(9) 0.0154(9) 0.0013(7) 0.0032(7) 0.0024(7) C19 0.0156(9) 0.0166(9) 0.0168(9) 0.0027(7) 0.0021(7) 0.0013(7) C20 0.0213(10) 0.0231(10) 0.0165(9) 0.0022(8) 0.0052(8) 0.0015(8) C21 0.0231(11) 0.0263(11) 0.0175(10) -0.0038(8) 0.0015(8) 0.0021(8) C22 0.0166(10) 0.0269(11) 0.0250(10) -0.0042(8) -0.0001(8) -0.0024(8) C23 0.0148(10) 0.0259(10) 0.0232(10) -0.0006(8) 0.0064(8) -0.0013(8) C24 0.0183(10) 0.0184(9) 0.0202(10) 0.0029(8) 0.0051(8) 0.0009(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 S1 C13 1.7980(19) . ? S1 S2 2.0573(8) . ? S2 C18 1.7986(19) . ? O1 C11 1.316(2) . ? O1 H1O 0.8401(11) . ? O2 C11 1.219(2) . ? O3 C24 1.318(2) . ? O3 H3O 0.8401(11) . ? O4 C24 1.212(2) . ? N1 C5 1.339(3) . ? N1 C1 1.335(3) . ? N2 C9 1.338(3) . ? N2 C8 1.336(3) . ? C1 C2 1.381(3) . ? C1 H1 0.9500 . ? C2 C3 1.397(3) . ? C2 H2 0.9500 . ? C3 C4 1.389(3) . ? C3 C6 1.490(3) . ? C4 C5 1.383(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.393(3) . ? C6 C10 1.391(3) . ? C7 C8 1.384(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.378(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.488(3) . ? C12 C13 1.407(3) . ? C12 C17 1.396(3) . ? C13 C14 1.396(3) . ? C14 C15 1.381(3) . ? C14 H14 0.9500 . ? C15 C16 1.384(3) . ? C15 H15 0.9500 . ? C16 C17 1.382(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C23 1.393(3) . ? C18 C19 1.406(3) . ? C19 C20 1.394(3) . ? C19 C24 1.486(3) . ? C20 C21 1.382(3) . ? C20 H20 0.9500 . ? C21 C22 1.382(3) . ? C21 H21 0.9500 . ? C22 C23 1.385(3) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? 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 C13 S1 S2 104.56(7) . . ? C18 S2 S1 104.51(7) . . ? C11 O1 H1O 111.6(19) . . ? C24 O3 H3O 114.4(18) . . ? C5 N1 C1 117.81(17) . . ? C9 N2 C8 117.11(18) . . ? N1 C1 C2 123.04(19) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C1 C2 C3 119.42(19) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 117.22(18) . . ? C4 C3 C6 121.32(18) . . ? C2 C3 C6 121.45(18) . . ? C3 C4 C5 119.64(18) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 122.83(19) . . ? N1 C5 H5 118.6 . . ? C4 C5 H5 118.6 . . ? C7 C6 C10 117.19(18) . . ? C7 C6 C3 121.01(18) . . ? C10 C6 C3 121.80(18) . . ? C6 C7 C8 119.54(19) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? N2 C8 C7 123.18(19) . . ? N2 C8 H8 118.4 . . ? C7 C8 H8 118.4 . . ? N2 C9 C10 123.6(2) . . ? N2 C9 H9 118.2 . . ? C10 C9 H9 118.2 . . ? C9 C10 C6 119.34(19) . . ? C9 C10 H10 120.3 . . ? C6 C10 H10 120.3 . . ? O2 C11 O1 124.01(18) . . ? O2 C11 C12 122.71(17) . . ? O1 C11 C12 113.28(17) . . ? C13 C12 C17 119.20(17) . . ? C13 C12 C11 121.59(17) . . ? C17 C12 C11 119.19(17) . . ? C12 C13 C14 118.52(17) . . ? C12 C13 S1 120.57(14) . . ? C14 C13 S1 120.91(14) . . ? C15 C14 C13 120.92(18) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C16 121.03(18) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C15 C16 C17 118.50(18) . . ? C15 C16 H16 120.7 . . ? C17 C16 H16 120.7 . . ? C12 C17 C16 121.77(18) . . ? C12 C17 H17 119.1 . . ? C16 C17 H17 119.1 . . ? C23 C18 C19 118.78(17) . . ? C23 C18 S2 121.46(15) . . ? C19 C18 S2 119.72(14) . . ? C18 C19 C20 119.12(18) . . ? C18 C19 C24 122.33(17) . . ? C20 C19 C24 118.54(17) . . ? C21 C20 C19 121.70(18) . . ? C21 C20 H20 119.1 . . ? C19 C20 H20 119.1 . . ? C20 C21 C22 118.83(18) . . ? C20 C21 H21 120.6 . . ? C22 C21 H21 120.6 . . ? C23 C22 C21 120.68(19) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C18 C23 C22 120.88(18) . . ? C18 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? O4 C24 O3 123.98(18) . . ? O4 C24 C19 123.22(18) . . ? O3 C24 C19 112.79(16) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.5 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.26 _refine_diff_density_min -0.26 _refine_diff_density_rms 0.056 # Attachment '2.CIF' data_(HO2C)C6H4SSC6H4(CO2H).{1,2-bis(pyridine)ethene}(2) _database_code_depnum_ccdc_archive 'CCDC 648104' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H20 N2 O4 S2' _chemical_formula_sum 'C26 H20 N2 O4 S2' _chemical_formula_weight 488.56 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 P21/c 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 10.6070(2) _cell_length_b 12.3972(2) _cell_length_c 17.3834(4) _cell_angle_alpha 90 _cell_angle_beta 90.323(1) _cell_angle_gamma 90 _cell_volume 2285.83(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5450 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour light-tan _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.270 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.893 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 28252 _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_av_sigmaI/netI 0.034 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.9 _diffrn_reflns_theta_max 26.5 _reflns_number_total 4740 _reflns_number_gt 3710 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006' _computing_publication_material SHELXL97 _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^)+(0.0684P)^2^+0.4034P] 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 4740 _refine_ls_number_parameters 313 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.056 _refine_ls_R_factor_gt 0.037 _refine_ls_wR_factor_ref 0.115 _refine_ls_wR_factor_gt 0.097 _refine_ls_goodness_of_fit_ref 1.09 _refine_ls_restrained_S_all 1.08 _refine_ls_shift/su_max <0.001 _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 0.21830(4) 0.29155(4) 0.39495(3) 0.02451(14) Uani 1 1 d . . . S2 S 0.38056(4) 0.33541(4) 0.33878(3) 0.02332(14) Uani 1 1 d . . . O1 O -0.10525(12) 0.34508(11) 0.54855(8) 0.0278(3) Uani 1 1 d D . . H1O H -0.1696(13) 0.3071(15) 0.5405(13) 0.042 Uiso 1 1 d D . . O2 O -0.01134(12) 0.24622(11) 0.45761(8) 0.0305(3) Uani 1 1 d . . . O3 O 0.62141(12) 0.52928(12) 0.18393(9) 0.0357(4) Uani 1 1 d D . . H3O H 0.6950(9) 0.5052(19) 0.1789(14) 0.054 Uiso 1 1 d D . . O4 O 0.59455(11) 0.38962(10) 0.26406(7) 0.0237(3) Uani 1 1 d . . . N1 N -0.32285(14) 0.24750(13) 0.54013(9) 0.0257(4) Uani 1 1 d . . . N2 N -1.15047(14) 0.03841(13) 0.65754(9) 0.0274(4) Uani 1 1 d . . . C1 C -0.37462(19) 0.18065(17) 0.48859(12) 0.0308(5) Uani 1 1 d . . . H1 H -0.3259 0.1595 0.4455 0.037 Uiso 1 1 calc R . . C2 C -0.49595(18) 0.14077(16) 0.49512(11) 0.0285(4) Uani 1 1 d . . . H2 H -0.5293 0.0942 0.4567 0.034 Uiso 1 1 calc R . . C3 C -0.56861(17) 0.16914(14) 0.55802(10) 0.0213(4) Uani 1 1 d . . . C4 C -0.51410(17) 0.23852(16) 0.61167(11) 0.0270(4) Uani 1 1 d . . . H4 H -0.5600 0.2601 0.6559 0.032 Uiso 1 1 calc R . . C5 C -0.39323(18) 0.27568(16) 0.60031(11) 0.0279(4) Uani 1 1 d . . . H5 H -0.3582 0.3238 0.6372 0.034 Uiso 1 1 calc R . . C6 C -0.69670(17) 0.12482(15) 0.56678(11) 0.0237(4) Uani 1 1 d . . . H6 H -0.7220 0.0693 0.5324 0.028 Uiso 1 1 calc R . . C7 C -0.77861(17) 0.15648(14) 0.61874(11) 0.0226(4) Uani 1 1 d . . . H7 H -0.7525 0.2127 0.6524 0.027 Uiso 1 1 calc R . . C8 C -0.90631(16) 0.11355(14) 0.62991(10) 0.0212(4) Uani 1 1 d . . . C9 C -0.98821(18) 0.16819(15) 0.67838(12) 0.0290(5) Uani 1 1 d . . . H9 H -0.9615 0.2324 0.7034 0.035 Uiso 1 1 calc R . . C10 C -1.10820(18) 0.12901(16) 0.69005(12) 0.0308(5) Uani 1 1 d . . . H10 H -1.1632 0.1683 0.7227 0.037 Uiso 1 1 calc R . . C11 C -1.07189(17) -0.01561(15) 0.61156(11) 0.0253(4) Uani 1 1 d . . . H11 H -1.1006 -0.0806 0.5885 0.030 Uiso 1 1 calc R . . C12 C -0.95062(17) 0.01897(15) 0.59608(10) 0.0230(4) Uani 1 1 d . . . H12 H -0.8981 -0.0215 0.5627 0.028 Uiso 1 1 calc R . . C13 C -0.00897(17) 0.31706(14) 0.50611(11) 0.0211(4) Uani 1 1 d . . . C14 C 0.10680(16) 0.38088(14) 0.52442(10) 0.0205(4) Uani 1 1 d . . . C15 C 0.21582(16) 0.37595(14) 0.47889(10) 0.0209(4) Uani 1 1 d . . . C16 C 0.32033(17) 0.43743(16) 0.50037(11) 0.0274(4) Uani 1 1 d . . . H16 H 0.3939 0.4359 0.4695 0.033 Uiso 1 1 calc R . . C17 C 0.31859(18) 0.50044(17) 0.56584(12) 0.0308(5) Uani 1 1 d . . . H17 H 0.3913 0.5408 0.5799 0.037 Uiso 1 1 calc R . . C18 C 0.21224(18) 0.50530(16) 0.61100(11) 0.0289(4) Uani 1 1 d . . . H18 H 0.2112 0.5486 0.6561 0.035 Uiso 1 1 calc R . . C19 C 0.10747(17) 0.44637(15) 0.58976(11) 0.0245(4) Uani 1 1 d . . . H19 H 0.0337 0.4504 0.6204 0.029 Uiso 1 1 calc R . . C20 C 0.33664(16) 0.45691(14) 0.28932(10) 0.0185(4) Uani 1 1 d . . . C21 C 0.42445(16) 0.51194(14) 0.24340(10) 0.0185(4) Uani 1 1 d . . . C22 C 0.38779(17) 0.60633(15) 0.20581(10) 0.0225(4) Uani 1 1 d . . . H22 H 0.4480 0.6449 0.1764 0.027 Uiso 1 1 calc R . . C23 C 0.26560(18) 0.64522(15) 0.21039(11) 0.0248(4) Uani 1 1 d . . . H23 H 0.2413 0.7083 0.1831 0.030 Uiso 1 1 calc R . . C24 C 0.17988(17) 0.59060(15) 0.25543(11) 0.0241(4) Uani 1 1 d . . . H24 H 0.0958 0.6165 0.2592 0.029 Uiso 1 1 calc R . . C25 C 0.21508(17) 0.49876(15) 0.29501(10) 0.0222(4) Uani 1 1 d . . . H25 H 0.1553 0.4634 0.3267 0.027 Uiso 1 1 calc R . . C26 C 0.55524(17) 0.47048(14) 0.23216(10) 0.0213(4) 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 0.0230(3) 0.0227(3) 0.0279(3) -0.0014(2) 0.00971(19) -0.00370(18) S2 0.0197(2) 0.0225(3) 0.0278(3) 0.00225(19) 0.00915(19) 0.00218(18) O1 0.0141(7) 0.0368(8) 0.0325(8) -0.0068(6) 0.0067(6) -0.0067(5) O2 0.0238(7) 0.0304(7) 0.0374(8) -0.0081(7) 0.0089(6) -0.0071(6) O3 0.0181(7) 0.0389(8) 0.0502(9) 0.0162(7) 0.0168(7) 0.0053(6) O4 0.0192(6) 0.0255(7) 0.0263(7) 0.0007(6) 0.0035(5) 0.0021(5) N1 0.0197(8) 0.0327(9) 0.0249(8) -0.0026(7) 0.0034(7) -0.0050(7) N2 0.0200(8) 0.0280(9) 0.0343(9) 0.0003(7) 0.0100(7) -0.0001(7) C1 0.0234(10) 0.0425(12) 0.0266(11) -0.0066(9) 0.0088(8) -0.0062(9) C2 0.0243(10) 0.0367(11) 0.0245(10) -0.0068(9) 0.0031(8) -0.0080(8) C3 0.0165(9) 0.0255(10) 0.0220(9) 0.0043(8) 0.0003(7) -0.0002(7) C4 0.0198(10) 0.0369(11) 0.0242(10) -0.0041(9) 0.0039(8) -0.0008(8) C5 0.0219(10) 0.0354(11) 0.0265(10) -0.0072(9) -0.0001(8) -0.0060(8) C6 0.0203(9) 0.0279(10) 0.0230(9) 0.0018(8) 0.0002(8) -0.0041(8) C7 0.0203(9) 0.0222(9) 0.0252(10) 0.0018(8) 0.0001(8) -0.0012(7) C8 0.0170(9) 0.0240(10) 0.0226(9) 0.0062(8) 0.0025(7) 0.0014(7) C9 0.0257(11) 0.0214(10) 0.0402(12) -0.0039(9) 0.0080(9) -0.0004(8) C10 0.0249(10) 0.0265(10) 0.0411(12) -0.0022(9) 0.0138(9) 0.0011(8) C11 0.0214(10) 0.0266(10) 0.0279(10) -0.0020(8) 0.0050(8) -0.0013(8) C12 0.0179(9) 0.0296(10) 0.0217(9) -0.0008(8) 0.0059(7) 0.0027(7) C13 0.0178(9) 0.0225(9) 0.0231(9) 0.0022(8) 0.0043(7) -0.0007(7) C14 0.0160(9) 0.0213(9) 0.0242(9) 0.0046(8) 0.0028(7) 0.0011(7) C15 0.0186(9) 0.0208(9) 0.0234(9) 0.0019(8) 0.0039(7) 0.0012(7) C16 0.0171(9) 0.0353(11) 0.0298(10) 0.0008(9) 0.0058(8) -0.0034(8) C17 0.0183(10) 0.0427(12) 0.0314(11) -0.0035(9) 0.0007(8) -0.0083(8) C18 0.0236(10) 0.0364(11) 0.0266(10) -0.0064(9) -0.0001(8) -0.0036(8) C19 0.0185(9) 0.0304(10) 0.0247(10) 0.0008(8) 0.0053(8) 0.0002(8) C20 0.0178(9) 0.0203(9) 0.0174(8) -0.0045(7) 0.0017(7) -0.0015(7) C21 0.0169(9) 0.0218(9) 0.0169(8) -0.0050(7) 0.0035(7) -0.0017(7) C22 0.0222(9) 0.0241(10) 0.0212(9) -0.0022(8) 0.0054(7) -0.0012(7) C23 0.0271(10) 0.0244(10) 0.0230(10) -0.0018(8) 0.0020(8) 0.0049(8) C24 0.0169(9) 0.0289(10) 0.0265(10) -0.0068(8) 0.0029(7) 0.0041(7) C25 0.0184(9) 0.0249(10) 0.0234(9) -0.0048(8) 0.0056(7) -0.0025(7) C26 0.0185(9) 0.0239(10) 0.0216(9) -0.0044(8) 0.0031(7) -0.0029(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 C15 1.7958(18) . ? S1 S2 2.0567(6) . ? S2 C20 1.7946(18) . ? O1 C13 1.310(2) . ? O1 H1O 0.8400(10) . ? O2 C13 1.218(2) . ? O3 C26 1.317(2) . ? O3 H3O 0.8402(10) . ? O4 C26 1.218(2) . ? N1 C1 1.336(2) . ? N1 C5 1.335(2) . ? N2 C10 1.334(3) . ? N2 C11 1.338(2) . ? C1 C2 1.384(3) . ? C1 H1 0.9500 . ? C2 C3 1.387(3) . ? C2 H2 0.9500 . ? C3 C4 1.392(3) . ? C3 C6 1.474(2) . ? C4 C5 1.378(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.317(3) . ? C6 H6 0.9500 . ? C7 C8 1.469(2) . ? C7 H7 0.9500 . ? C8 C9 1.390(3) . ? C8 C12 1.392(3) . ? C9 C10 1.378(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.384(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.494(2) . ? C14 C19 1.396(3) . ? C14 C15 1.406(2) . ? C15 C16 1.394(2) . ? C16 C17 1.381(3) . ? C16 H16 0.9500 . ? C17 C18 1.379(3) . ? C17 H17 0.9500 . ? C18 C19 1.379(3) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C25 1.394(2) . ? C20 C21 1.407(2) . ? C21 C22 1.395(3) . ? C21 C26 1.493(2) . ? C22 C23 1.386(3) . ? C22 H22 0.9500 . ? C23 C24 1.381(3) . ? C23 H23 0.9500 . ? C24 C25 1.381(3) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? 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 C15 S1 S2 104.35(6) . . ? C20 S2 S1 103.51(6) . . ? C13 O1 H1O 113.1(16) . . ? C26 O3 H3O 111.6(18) . . ? C1 N1 C5 117.27(16) . . ? C10 N2 C11 117.75(17) . . ? N1 C1 C2 123.05(19) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C3 C2 C1 119.70(18) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C4 C3 C2 117.02(17) . . ? C4 C3 C6 122.73(17) . . ? C2 C3 C6 120.24(17) . . ? C3 C4 C5 119.60(18) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 123.35(18) . . ? N1 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? C7 C6 C3 124.88(18) . . ? C7 C6 H6 117.6 . . ? C3 C6 H6 117.6 . . ? C6 C7 C8 126.52(18) . . ? C6 C7 H7 116.7 . . ? C8 C7 H7 116.7 . . ? C9 C8 C12 117.11(17) . . ? C9 C8 C7 118.91(17) . . ? C12 C8 C7 123.95(17) . . ? C8 C9 C10 119.89(18) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? N2 C10 C9 122.88(19) . . ? N2 C10 H10 118.6 . . ? C9 C10 H10 118.6 . . ? N2 C11 C12 122.97(18) . . ? N2 C11 H11 118.5 . . ? C12 C11 H11 118.5 . . ? C11 C12 C8 119.39(17) . . ? C11 C12 H12 120.3 . . ? C8 C12 H12 120.3 . . ? O2 C13 O1 124.62(17) . . ? O2 C13 C14 122.92(17) . . ? O1 C13 C14 112.46(16) . . ? C19 C14 C15 118.87(16) . . ? C19 C14 C13 118.80(16) . . ? C15 C14 C13 122.32(16) . . ? C16 C15 C14 118.72(17) . . ? C16 C15 S1 121.38(14) . . ? C14 C15 S1 119.90(13) . . ? C17 C16 C15 121.05(18) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C16 C17 C18 120.57(18) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C19 C18 C17 119.02(18) . . ? C19 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? C14 C19 C18 121.76(18) . . ? C14 C19 H19 119.1 . . ? C18 C19 H19 119.1 . . ? C25 C20 C21 118.39(16) . . ? C25 C20 S2 121.07(14) . . ? C21 C20 S2 120.54(13) . . ? C22 C21 C20 119.29(16) . . ? C22 C21 C26 118.96(16) . . ? C20 C21 C26 121.73(16) . . ? C21 C22 C23 121.56(17) . . ? C21 C22 H22 119.2 . . ? C23 C22 H22 119.2 . . ? C24 C23 C22 118.76(17) . . ? C24 C23 H23 120.6 . . ? C22 C23 H23 120.6 . . ? C23 C24 C25 120.66(17) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C20 C25 C24 121.28(17) . . ? C20 C25 H25 119.4 . . ? C24 C25 H25 119.4 . . ? O4 C26 O3 124.28(17) . . ? O4 C26 C21 122.66(16) . . ? O3 C26 C21 113.06(15) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.5 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.31 _refine_diff_density_min -0.45 _refine_diff_density_rms 0.071 # Attachment '3.CIF' data_(HO2C)C6H4SSC6H4(CO2H).{1,2-bis(pyridine)ethane}(3) _database_code_depnum_ccdc_archive 'CCDC 648105' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H22 N2 O4 S2' _chemical_formula_sum 'C26 H22 N2 O4 S2' _chemical_formula_weight 490.58 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.8615(9) _cell_length_b 10.1880(4) _cell_length_c 19.9562(8) _cell_angle_alpha 90 _cell_angle_beta 125.715(2) _cell_angle_gamma 90 _cell_volume 4764.4(3) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5604 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2048 _exptl_absorpt_coefficient_mu 0.260 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.736 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 27316 _diffrn_reflns_av_R_equivalents 0.064 _diffrn_reflns_av_sigmaI/netI 0.056 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.7 _diffrn_reflns_theta_max 26.5 _reflns_number_total 4938 _reflns_number_gt 3297 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006' _computing_publication_material SHELXL97 _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^)+(0.0769P)^2^+3.6574P] 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 4938 _refine_ls_number_parameters 350 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.096 _refine_ls_R_factor_gt 0.053 _refine_ls_wR_factor_ref 0.153 _refine_ls_wR_factor_gt 0.130 _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_restrained_S_all 1.06 _refine_ls_shift/su_max <0.001 _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 0.11207(3) 0.86354(7) 0.43387(4) 0.0388(2) Uani 1 1 d . . . S2 S 0.12251(3) 1.04926(7) 0.40438(5) 0.0418(2) Uani 1 1 d . . . O1 O 0.10724(10) 0.5484(2) 0.57932(14) 0.0488(5) Uani 1 1 d D . . H1O H 0.0866(13) 0.487(3) 0.5479(19) 0.073 Uiso 1 1 d D . . O2 O 0.08147(8) 0.6373(2) 0.46002(13) 0.0457(5) Uani 1 1 d . . . O3 O 0.19967(10) 1.36825(19) 0.35201(14) 0.0465(5) Uani 1 1 d D . . H3O H 0.1748(11) 1.427(3) 0.328(2) 0.070 Uiso 1 1 d D . . O4 O 0.12529(8) 1.2792(2) 0.34296(12) 0.0471(5) Uani 1 1 d . . . N2 N -0.14157(11) -0.4173(2) 0.20588(15) 0.0464(6) Uani 1 1 d . A . N1 N 0.04568(12) 0.3528(2) 0.48400(18) 0.0478(7) Uani 0.731(5) 1 d P A 1 C3 C -0.02919(14) 0.1518(3) 0.3831(2) 0.0468(8) Uani 0.731(5) 1 d P A 1 C1 C 0.02789(19) 0.3356(5) 0.4028(3) 0.0437(12) Uani 0.731(5) 1 d P A 1 H1 H 0.0417 0.3946 0.3814 0.052 Uiso 0.731(5) 1 calc PR A 1 C2 C -0.0090(2) 0.2363(5) 0.3521(3) 0.0431(12) Uani 0.731(5) 1 d P A 1 H2 H -0.0199 0.2269 0.2972 0.052 Uiso 0.731(5) 1 calc PR A 1 C4 C -0.01365(16) 0.1698(4) 0.4614(2) 0.0379(11) Uani 0.731(5) 1 d P A 1 H4 H -0.0282 0.1139 0.4832 0.045 Uiso 0.731(5) 1 calc PR A 1 C5 C 0.02335(17) 0.2700(4) 0.5085(2) 0.0396(11) Uani 0.731(5) 1 d P A 1 H5 H 0.0336 0.2803 0.5629 0.048 Uiso 0.731(5) 1 calc PR A 1 N1' N 0.04568(12) 0.3528(2) 0.48400(18) 0.0478(7) Uani 0.269(5) 1 d P A 2 C3' C -0.02919(14) 0.1518(3) 0.3831(2) 0.0468(8) Uani 0.269(5) 1 d P A 2 C1A C 0.0041(7) 0.3761(13) 0.4233(11) 0.069(5) Uani 0.269(5) 1 d P A 2 H1A H -0.0080 0.4647 0.4086 0.083 Uiso 0.269(5) 1 calc PR A 2 C2A C -0.0296(7) 0.2749(15) 0.3699(11) 0.075(5) Uani 0.269(5) 1 d P A 2 H2A H -0.0574 0.3015 0.3145 0.090 Uiso 0.269(5) 1 calc PR A 2 C4A C 0.0313(7) 0.1258(13) 0.4656(12) 0.082(5) Uani 0.269(5) 1 d P A 2 H4A H 0.0443 0.0377 0.4795 0.098 Uiso 0.269(5) 1 calc PR A 2 C5A C 0.0676(6) 0.2273(13) 0.5205(9) 0.064(4) Uani 0.269(5) 1 d P A 2 H5A H 0.1016 0.2132 0.5741 0.077 Uiso 0.269(5) 1 calc PR A 2 C6 C -0.07091(14) 0.0441(3) 0.3292(2) 0.0494(8) Uani 1 1 d . . . H6A H -0.0890 0.0098 0.3552 0.059 Uiso 1 1 calc R A 1 H6B H -0.1013 0.0815 0.2749 0.059 Uiso 1 1 calc R A 1 C7 C -0.04247(13) -0.0667(3) 0.3168(2) 0.0497(8) Uani 1 1 d . A . H7A H -0.0077 -0.0917 0.3712 0.060 Uiso 1 1 calc R . . H7B H -0.0302 -0.0344 0.2826 0.060 Uiso 1 1 calc R . . C8 C -0.07820(12) -0.1876(3) 0.27654(18) 0.0424(7) Uani 1 1 d . . . C9 C -0.13709(12) -0.1888(3) 0.23465(18) 0.0418(7) Uani 1 1 d . A . H9 H -0.1568 -0.1106 0.2298 0.050 Uiso 1 1 calc R . . C10 C -0.16667(13) -0.3039(3) 0.20018(18) 0.0422(7) Uani 1 1 d . . . H10 H -0.2070 -0.3025 0.1709 0.051 Uiso 1 1 calc R A . C11 C -0.08528(15) -0.4157(4) 0.2446(2) 0.0650(10) Uani 1 1 d . . . H11 H -0.0668 -0.4948 0.2475 0.078 Uiso 1 1 calc R A . C12 C -0.05277(14) -0.3052(4) 0.2805(2) 0.0612(10) Uani 1 1 d . A . H12 H -0.0126 -0.3094 0.3082 0.073 Uiso 1 1 calc R . . C14 C 0.14376(10) 0.7576(3) 0.58333(17) 0.0340(6) Uani 1 1 d . . . C15 C 0.14798(10) 0.8662(3) 0.54341(17) 0.0330(6) Uani 1 1 d . . . C16 C 0.18199(11) 0.9718(3) 0.59103(18) 0.0379(7) Uani 1 1 d . . . H16 H 0.1853 1.0453 0.5648 0.045 Uiso 1 1 calc R . . C17 C 0.21100(13) 0.9715(3) 0.67556(19) 0.0462(8) Uani 1 1 d . . . H17 H 0.2338 1.0449 0.7069 0.055 Uiso 1 1 calc R . . C18 C 0.20716(13) 0.8645(3) 0.71518(19) 0.0477(8) Uani 1 1 d . . . H18 H 0.2274 0.8640 0.7735 0.057 Uiso 1 1 calc R . . C19 C 0.17356(12) 0.7586(3) 0.66880(18) 0.0411(7) Uani 1 1 d . . . H19 H 0.1708 0.6854 0.6957 0.049 Uiso 1 1 calc R . . C13 C 0.10760(11) 0.6425(3) 0.53468(19) 0.0379(7) Uani 1 1 d . . . C21 C 0.21204(12) 1.1594(3) 0.40913(16) 0.0329(6) Uani 1 1 d . . . C20 C 0.19305(11) 1.0486(3) 0.42846(16) 0.0334(6) Uani 1 1 d . . . C22 C 0.26830(13) 1.1611(3) 0.43336(18) 0.0403(7) Uani 1 1 d . . . H22 H 0.2816 1.2357 0.4208 0.048 Uiso 1 1 calc R . . C23 C 0.30490(12) 1.0574(3) 0.47496(18) 0.0395(7) Uani 1 1 d . . . H23 H 0.3432 1.0612 0.4917 0.047 Uiso 1 1 calc R . . C24 C 0.28530(12) 0.9478(3) 0.49209(17) 0.0377(7) Uani 1 1 d . . . H24 H 0.3099 0.8750 0.5196 0.045 Uiso 1 1 calc R . . C25 C 0.22989(11) 0.9438(3) 0.46928(16) 0.0366(7) Uani 1 1 d . . . H25 H 0.2169 0.8683 0.4817 0.044 Uiso 1 1 calc R . . C26 C 0.17443(13) 1.2739(3) 0.36472(16) 0.0373(7) 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 0.0291(4) 0.0384(4) 0.0322(4) 0.0073(3) 0.0084(3) -0.0079(3) S2 0.0318(4) 0.0386(4) 0.0388(4) 0.0120(3) 0.0115(3) -0.0037(3) O1 0.0605(14) 0.0348(12) 0.0554(15) 0.0066(10) 0.0363(13) -0.0077(10) O2 0.0360(11) 0.0424(13) 0.0398(13) 0.0055(10) 0.0114(10) -0.0119(9) O3 0.0692(15) 0.0273(11) 0.0561(14) 0.0028(10) 0.0439(13) -0.0044(10) O4 0.0437(12) 0.0398(12) 0.0384(12) 0.0097(9) 0.0130(10) -0.0070(9) N2 0.0546(16) 0.0370(15) 0.0379(15) -0.0019(12) 0.0215(13) 0.0075(12) N1 0.0513(17) 0.0363(16) 0.0613(19) 0.0033(13) 0.0360(16) -0.0064(13) C3 0.0504(19) 0.0382(19) 0.051(2) -0.0032(15) 0.0290(17) -0.0037(14) C1 0.044(2) 0.045(3) 0.040(3) 0.007(2) 0.023(2) -0.010(2) C2 0.040(3) 0.048(3) 0.040(3) 0.000(2) 0.022(2) -0.004(2) C4 0.038(2) 0.035(2) 0.038(2) 0.0022(17) 0.0208(19) -0.0057(17) C5 0.046(3) 0.040(2) 0.034(2) -0.0007(18) 0.023(2) -0.0074(19) N1 0.0513(17) 0.0363(16) 0.0613(19) 0.0033(13) 0.0360(16) -0.0064(13) C3 0.0504(19) 0.0382(19) 0.051(2) -0.0032(15) 0.0290(17) -0.0037(14) C1A 0.053(9) 0.032(8) 0.077(11) -0.015(7) 0.012(9) -0.001(6) C2A 0.057(10) 0.039(9) 0.064(11) 0.003(7) -0.001(8) -0.006(7) C4A 0.095(12) 0.021(7) 0.137(16) -0.010(8) 0.073(12) -0.004(7) C5A 0.045(7) 0.044(8) 0.081(10) 0.006(7) 0.023(7) -0.002(6) C6 0.0483(18) 0.0432(19) 0.0486(19) -0.0028(15) 0.0237(16) -0.0027(15) C7 0.0377(16) 0.060(2) 0.0463(19) -0.0059(16) 0.0217(15) -0.0033(15) C8 0.0396(16) 0.0457(18) 0.0349(16) -0.0031(14) 0.0178(14) 0.0010(14) C9 0.0386(16) 0.0366(17) 0.0433(17) -0.0027(14) 0.0201(14) 0.0038(13) C10 0.0404(16) 0.0386(18) 0.0443(18) -0.0055(14) 0.0228(15) 0.0003(14) C11 0.056(2) 0.052(2) 0.056(2) -0.0099(18) 0.0151(18) 0.0201(18) C12 0.0398(17) 0.067(2) 0.055(2) -0.0139(19) 0.0152(16) 0.0145(17) C14 0.0277(13) 0.0356(16) 0.0402(16) 0.0049(13) 0.0206(13) 0.0002(12) C15 0.0237(12) 0.0369(16) 0.0358(15) 0.0029(12) 0.0158(12) -0.0014(11) C16 0.0352(15) 0.0374(17) 0.0423(17) -0.0007(13) 0.0234(14) -0.0088(12) C17 0.0439(17) 0.056(2) 0.0460(19) -0.0139(15) 0.0305(16) -0.0185(15) C18 0.0471(17) 0.065(2) 0.0342(16) -0.0004(15) 0.0257(15) -0.0046(16) C19 0.0397(16) 0.0468(18) 0.0426(18) 0.0053(14) 0.0274(15) -0.0005(14) C13 0.0311(14) 0.0342(16) 0.0495(19) 0.0066(14) 0.0242(15) 0.0008(12) C21 0.0443(15) 0.0308(15) 0.0212(13) -0.0052(11) 0.0178(12) -0.0074(12) C20 0.0354(14) 0.0359(16) 0.0227(14) -0.0018(12) 0.0135(12) -0.0087(12) C22 0.0588(19) 0.0319(16) 0.0415(17) -0.0095(13) 0.0356(16) -0.0134(14) C23 0.0424(16) 0.0385(17) 0.0451(18) -0.0085(14) 0.0298(15) -0.0075(13) C24 0.0413(16) 0.0374(17) 0.0329(16) -0.0017(12) 0.0209(13) -0.0037(13) C25 0.0370(15) 0.0360(16) 0.0304(15) 0.0029(12) 0.0161(13) -0.0076(12) C26 0.0521(18) 0.0322(16) 0.0254(14) -0.0061(12) 0.0214(14) -0.0099(13) _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 C15 1.791(3) . ? S1 S2 2.0552(10) . ? S2 C20 1.798(3) . ? O1 C13 1.313(3) . ? O2 C13 1.216(3) . ? O3 C26 1.317(3) . ? O4 C26 1.218(3) . ? N2 C10 1.333(4) . ? N2 C11 1.331(4) . ? N1 C5 1.317(4) . ? N1 C1 1.395(5) . ? C3 C4 1.362(5) . ? C3 C2 1.374(5) . ? C3 C6 1.515(4) . ? C1 C2 1.387(6) . ? C4 C5 1.377(5) . ? N1 C1A 1.125(15) . ? N1 C5A 1.425(14) . ? C3 C2A 1.281(15) . ? C3 C6 1.515(4) . ? C3 C4A 1.573(18) . ? C1A C2A 1.391(19) . ? C4A C5A 1.42(2) . ? C6 C7 1.500(4) . ? C7 C8 1.503(4) . ? C8 C12 1.383(4) . ? C8 C9 1.389(4) . ? C9 C10 1.376(4) . ? C11 C12 1.370(5) . ? C14 C19 1.392(4) . ? C14 C15 1.409(4) . ? C14 C13 1.492(4) . ? C15 C16 1.391(4) . ? C16 C17 1.378(4) . ? C17 C18 1.388(4) . ? C18 C19 1.383(4) . ? C21 C22 1.398(4) . ? C21 C20 1.403(4) . ? C21 C26 1.483(4) . ? C20 C25 1.387(4) . ? C22 C23 1.377(4) . ? C23 C24 1.382(4) . ? C24 C25 1.384(4) . ? 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 C15 S1 S2 104.97(9) . . ? C20 S2 S1 104.63(9) . . ? C10 N2 C11 117.2(3) . . ? C5 N1 C1 115.0(3) . . ? C4 C3 C2 119.3(3) . . ? C4 C3 C6 120.3(3) . . ? C2 C3 C6 120.3(3) . . ? C2 C1 N1 123.1(4) . . ? C3 C2 C1 118.3(4) . . ? C3 C4 C5 119.2(3) . . ? N1 C5 C4 125.0(4) . . ? C1A N1 C5A 128.0(9) . . ? C2A C3 C6 130.9(7) . . ? C2A C3 C4A 104.6(8) . . ? C6 C3 C4A 123.9(5) . . ? N1 C1A C2A 119.9(13) . . ? C3 C2A C1A 130.5(14) . . ? C5A C4A C3 123.5(11) . . ? C4A C5A N1 110.6(12) . . ? C7 C6 C3 112.2(3) . . ? C7 C6 C3 112.2(3) . . ? C3 C6 C3 0.0(5) . . ? C6 C7 C8 115.7(2) . . ? C12 C8 C9 116.7(3) . . ? C12 C8 C7 120.3(3) . . ? C9 C8 C7 123.1(3) . . ? C10 C9 C8 119.5(3) . . ? N2 C10 C9 123.3(3) . . ? N2 C11 C12 123.0(3) . . ? C11 C12 C8 120.2(3) . . ? C19 C14 C15 119.5(3) . . ? C19 C14 C13 120.0(3) . . ? C15 C14 C13 120.5(2) . . ? C16 C15 C14 118.7(3) . . ? C16 C15 S1 121.4(2) . . ? C14 C15 S1 119.9(2) . . ? C17 C16 C15 121.1(3) . . ? C16 C17 C18 120.4(3) . . ? C19 C18 C17 119.3(3) . . ? C18 C19 C14 121.1(3) . . ? O2 C13 O1 123.7(3) . . ? O2 C13 C14 122.0(2) . . ? O1 C13 C14 114.3(3) . . ? C22 C21 C20 118.4(3) . . ? C22 C21 C26 119.6(2) . . ? C20 C21 C26 122.0(2) . . ? C25 C20 C21 119.5(2) . . ? C25 C20 S2 121.3(2) . . ? C21 C20 S2 119.1(2) . . ? C23 C22 C21 121.8(3) . . ? C22 C23 C24 119.2(3) . . ? C23 C24 C25 120.2(3) . . ? C24 C25 C20 120.8(3) . . ? O4 C26 O3 123.9(3) . . ? O4 C26 C21 122.8(2) . . ? O3 C26 C21 113.3(2) . . ? 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 C15 S1 S2 C20 80.80(12) . . . . ? C5 N1 C1 C2 -2.2(7) . . . . ? C4 C3 C2 C1 1.5(7) . . . . ? C6 C3 C2 C1 178.2(4) . . . . ? N1 C1 C2 C3 0.6(8) . . . . ? C2 C3 C4 C5 -1.9(6) . . . . ? C6 C3 C4 C5 -178.6(3) . . . . ? C1 N1 C5 C4 1.8(6) . . . . ? C3 C4 C5 N1 0.2(6) . . . . ? C5A N1 C1A C2A -8(3) . . . . ? C6 C3 C2A C1A 169.5(16) . . . . ? C4A C3 C2A C1A -20(3) . . . . ? N1 C1A C2A C3 18(4) . . . . ? C2A C3 C4A C5A 15.6(19) . . . . ? C6 C3 C4A C5A -172.6(11) . . . . ? C3 C4A C5A N1 -9.5(19) . . . . ? C1A N1 C5A C4A 5(2) . . . . ? C4 C3 C6 C7 -108.7(4) . . . . ? C2 C3 C6 C7 74.7(4) . . . . ? C4 C3 C6 C3 0(100) . . . . ? C2 C3 C6 C3 0(28) . . . . ? C2A C3 C6 C7 124.5(15) . . . . ? C4A C3 C6 C7 -45.0(8) . . . . ? C2A C3 C6 C3 0(100) . . . . ? C4A C3 C6 C3 0(100) . . . . ? C3 C6 C7 C8 169.9(3) . . . . ? C3 C6 C7 C8 169.9(3) . . . . ? C6 C7 C8 C12 -163.9(3) . . . . ? C6 C7 C8 C9 15.7(4) . . . . ? C12 C8 C9 C10 0.3(4) . . . . ? C7 C8 C9 C10 -179.4(3) . . . . ? C11 N2 C10 C9 -2.5(5) . . . . ? C8 C9 C10 N2 1.2(5) . . . . ? C10 N2 C11 C12 2.4(5) . . . . ? N2 C11 C12 C8 -1.0(6) . . . . ? C9 C8 C12 C11 -0.3(5) . . . . ? C7 C8 C12 C11 179.3(3) . . . . ? C19 C14 C15 C16 0.0(4) . . . . ? C13 C14 C15 C16 179.8(2) . . . . ? C19 C14 C15 S1 177.6(2) . . . . ? C13 C14 C15 S1 -2.6(3) . . . . ? S2 S1 C15 C16 -9.5(2) . . . . ? S2 S1 C15 C14 172.94(18) . . . . ? C14 C15 C16 C17 -0.3(4) . . . . ? S1 C15 C16 C17 -177.9(2) . . . . ? C15 C16 C17 C18 0.5(4) . . . . ? C16 C17 C18 C19 -0.5(4) . . . . ? C17 C18 C19 C14 0.2(4) . . . . ? C15 C14 C19 C18 0.1(4) . . . . ? C13 C14 C19 C18 -179.7(3) . . . . ? C19 C14 C13 O2 -179.1(3) . . . . ? C15 C14 C13 O2 1.0(4) . . . . ? C19 C14 C13 O1 0.1(4) . . . . ? C15 C14 C13 O1 -179.7(2) . . . . ? C22 C21 C20 C25 -1.2(4) . . . . ? C26 C21 C20 C25 179.3(2) . . . . ? C22 C21 C20 S2 175.64(19) . . . . ? C26 C21 C20 S2 -3.9(3) . . . . ? S1 S2 C20 C25 -8.2(2) . . . . ? S1 S2 C20 C21 175.04(18) . . . . ? C20 C21 C22 C23 0.3(4) . . . . ? C26 C21 C22 C23 179.8(3) . . . . ? C21 C22 C23 C24 1.1(4) . . . . ? C22 C23 C24 C25 -1.4(4) . . . . ? C23 C24 C25 C20 0.5(4) . . . . ? C21 C20 C25 C24 0.8(4) . . . . ? S2 C20 C25 C24 -175.9(2) . . . . ? C22 C21 C26 O4 -179.0(3) . . . . ? C20 C21 C26 O4 0.5(4) . . . . ? C22 C21 C26 O3 0.6(3) . . . . ? C20 C21 C26 O3 -179.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.5 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.62 _refine_diff_density_min -0.32 _refine_diff_density_rms 0.075 # Attachment '4.CIF' data_(HO2C)C6H4SSC6H4(CO2H).{1,2-bis(pyridine)ethane}.2H2O(4) _database_code_depnum_ccdc_archive 'CCDC 648106' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H26 N2 O6 S2' _chemical_formula_sum 'C26 H26 N2 O6 S2' _chemical_formula_weight 526.61 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 7.5501(15) _cell_length_b 9.0077(18) _cell_length_c 18.787(4) _cell_angle_alpha 88.56(3) _cell_angle_beta 81.33(3) _cell_angle_gamma 74.86(3) _cell_volume 1219.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4221 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 30.5 _exptl_crystal_description fragment _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.265 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.933 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC12\K/SATURN724 _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% '< 1' _diffrn_reflns_number 24047 _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_av_sigmaI/netI 0.020 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.2 _diffrn_reflns_theta_max 26.5 _reflns_number_total 5052 _reflns_number_gt 4904 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) & DIAMOND (Crystal Impact, 2006)' _computing_publication_material SHELXL97 _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^)+(0.0387P)^2^+0.5839P] 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 5052 _refine_ls_number_parameters 343 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.036 _refine_ls_R_factor_gt 0.034 _refine_ls_wR_factor_ref 0.087 _refine_ls_wR_factor_gt 0.086 _refine_ls_goodness_of_fit_ref 1.08 _refine_ls_restrained_S_all 1.08 _refine_ls_shift/su_max 0.001 _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 0.31381(5) 0.85428(4) 0.681687(18) 0.02521(10) Uani 1 1 d . . . S2 S 0.31673(5) 0.96208(4) 0.776491(18) 0.02399(10) Uani 1 1 d . . . O1 O 0.47086(17) 0.72652(18) 0.45161(6) 0.0452(3) Uani 1 1 d D . . H1O H 0.395(3) 0.692(3) 0.4329(12) 0.068 Uiso 1 1 d D . . O2 O 0.28465(16) 0.73455(15) 0.55674(6) 0.0364(3) Uani 1 1 d . . . O3 O 0.24266(16) 0.98644(12) 1.00769(6) 0.0331(3) Uani 1 1 d . . . O4 O 0.29669(15) 1.11084(11) 0.90562(6) 0.0287(2) Uani 1 1 d . . . O5 O 0.10254(16) 0.78245(13) 1.09566(6) 0.0351(3) Uani 1 1 d D . . H1W H 0.142(2) 0.835(2) 1.0625(8) 0.053 Uiso 1 1 d D . . H2W H -0.01396(19) 0.809(2) 1.1038(11) 0.053 Uiso 1 1 d D . . O6 O 0.65912(16) 1.12353(14) 0.81733(7) 0.0381(3) Uani 1 1 d D . . H3W H 0.724(2) 1.156(3) 0.8428(8) 0.057 Uiso 1 1 d D . . H4W H 0.5577(14) 1.122(3) 0.8424(8) 0.057 Uiso 1 1 d D . . N1 N 0.23323(19) 0.63540(16) 0.38642(7) 0.0327(3) Uani 1 1 d . . . N2 N 0.05590(17) 0.22683(14) 0.08878(7) 0.0277(3) Uani 1 1 d D . . H2N H 0.123(2) 0.1508(15) 0.0599(8) 0.042 Uiso 1 1 d D . . C1 C 0.1353(2) 0.5381(2) 0.41429(9) 0.0350(4) Uani 1 1 d . . . H1 H 0.1725 0.4798 0.4548 0.042 Uiso 1 1 calc R . . C2 C -0.0170(2) 0.51805(18) 0.38719(8) 0.0315(3) Uani 1 1 d . . . H2 H -0.0803 0.4457 0.4083 0.038 Uiso 1 1 calc R . . C3 C -0.0774(2) 0.60431(16) 0.32875(8) 0.0254(3) Uani 1 1 d . . . C4 C 0.0278(2) 0.70227(18) 0.29830(8) 0.0295(3) Uani 1 1 d . . . H4 H -0.0051 0.7609 0.2573 0.035 Uiso 1 1 calc R . . C5 C 0.1807(2) 0.71373(19) 0.32818(9) 0.0329(3) Uani 1 1 d . . . H5 H 0.2517 0.7802 0.3064 0.039 Uiso 1 1 calc R . . C6 C -0.2565(2) 0.59725(19) 0.30403(8) 0.0305(3) Uani 1 1 d . . . H6A H -0.3574 0.6826 0.3278 0.037 Uiso 1 1 calc R . . H6B H -0.2847 0.4999 0.3211 0.037 Uiso 1 1 calc R . . C7 C -0.2607(2) 0.60656(17) 0.22300(8) 0.0274(3) Uani 1 1 d . . . H7A H -0.3910 0.6229 0.2150 0.033 Uiso 1 1 calc R . . H7B H -0.2203 0.6986 0.2052 0.033 Uiso 1 1 calc R . . C8 C -0.14417(19) 0.47043(16) 0.17771(8) 0.0226(3) Uani 1 1 d . . . C9 C -0.0338(2) 0.33944(16) 0.20520(8) 0.0242(3) Uani 1 1 d . . . H9 H -0.0270 0.3331 0.2553 0.029 Uiso 1 1 calc R . . C10 C 0.0658(2) 0.21876(17) 0.15953(8) 0.0267(3) Uani 1 1 d . . . H10 H 0.1416 0.1297 0.1783 0.032 Uiso 1 1 calc R . . C11 C -0.0486(2) 0.35142(18) 0.06022(8) 0.0299(3) Uani 1 1 d . . . H11 H -0.0534 0.3542 0.0099 0.036 Uiso 1 1 calc R . . C12 C -0.1483(2) 0.47434(17) 0.10325(8) 0.0270(3) Uani 1 1 d . . . H12 H -0.2206 0.5627 0.0826 0.032 Uiso 1 1 calc R . . C13 C 0.4229(2) 0.75751(18) 0.52095(8) 0.0266(3) Uani 1 1 d . . . C14 C 0.55749(19) 0.82037(16) 0.55302(8) 0.0239(3) Uani 1 1 d . . . C15 C 0.52746(19) 0.86214(16) 0.62648(8) 0.0228(3) Uani 1 1 d . . . C16 C 0.6664(2) 0.90755(18) 0.65510(9) 0.0291(3) Uani 1 1 d . . . H16 H 0.6479 0.9363 0.7045 0.035 Uiso 1 1 calc R . . C17 C 0.8312(2) 0.91066(19) 0.61145(10) 0.0335(3) Uani 1 1 d . . . H17 H 0.9261 0.9384 0.6317 0.040 Uiso 1 1 calc R . . C18 C 0.8590(2) 0.87388(19) 0.53864(9) 0.0331(3) Uani 1 1 d . . . H18 H 0.9712 0.8783 0.5091 0.040 Uiso 1 1 calc R . . C19 C 0.7220(2) 0.83076(18) 0.50948(8) 0.0290(3) Uani 1 1 d . . . H19 H 0.7393 0.8079 0.4594 0.035 Uiso 1 1 calc R . . C20 C 0.43440(18) 0.81333(15) 0.83119(7) 0.0206(3) Uani 1 1 d . . . C21 C 0.41897(18) 0.83954(15) 0.90591(7) 0.0205(3) Uani 1 1 d . . . C22 C 0.50477(19) 0.72125(16) 0.94868(8) 0.0243(3) Uani 1 1 d . . . H22 H 0.4929 0.7379 0.9991 0.029 Uiso 1 1 calc R . . C23 C 0.6072(2) 0.57973(16) 0.91862(8) 0.0260(3) Uani 1 1 d . . . H23 H 0.6657 0.5005 0.9482 0.031 Uiso 1 1 calc R . . C24 C 0.6232(2) 0.55536(16) 0.84493(8) 0.0262(3) Uani 1 1 d . . . H24 H 0.6934 0.4589 0.8241 0.031 Uiso 1 1 calc R . . C25 C 0.5375(2) 0.67064(16) 0.80136(8) 0.0243(3) Uani 1 1 d . . . H25 H 0.5490 0.6523 0.7511 0.029 Uiso 1 1 calc R . . C26 C 0.31176(19) 0.99110(16) 0.94189(7) 0.0226(3) 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 0.02283(18) 0.0350(2) 0.01926(17) -0.00187(14) -0.00256(13) -0.01019(14) S2 0.02724(18) 0.02248(18) 0.02011(17) -0.00086(13) -0.00462(13) -0.00202(13) O1 0.0382(7) 0.0797(10) 0.0236(6) -0.0155(6) 0.0014(5) -0.0274(7) O2 0.0306(6) 0.0578(8) 0.0266(6) -0.0050(5) -0.0026(5) -0.0223(5) O3 0.0448(7) 0.0254(5) 0.0224(5) -0.0045(4) 0.0071(5) -0.0038(5) O4 0.0364(6) 0.0200(5) 0.0257(5) -0.0006(4) -0.0024(4) -0.0016(4) O5 0.0343(6) 0.0340(6) 0.0356(6) 0.0050(5) -0.0059(5) -0.0062(5) O6 0.0359(6) 0.0413(7) 0.0390(7) 0.0032(5) -0.0083(5) -0.0120(5) N1 0.0340(7) 0.0401(8) 0.0249(6) -0.0049(5) -0.0058(5) -0.0099(6) N2 0.0275(6) 0.0245(6) 0.0292(7) -0.0085(5) 0.0032(5) -0.0068(5) C1 0.0403(9) 0.0372(9) 0.0248(8) 0.0048(6) -0.0057(7) -0.0052(7) C2 0.0385(8) 0.0292(8) 0.0263(8) 0.0016(6) -0.0003(6) -0.0108(6) C3 0.0289(7) 0.0250(7) 0.0202(7) -0.0078(5) 0.0015(6) -0.0057(6) C4 0.0368(8) 0.0302(8) 0.0226(7) 0.0019(6) -0.0055(6) -0.0101(6) C5 0.0397(9) 0.0333(8) 0.0288(8) -0.0011(6) -0.0039(7) -0.0155(7) C6 0.0276(8) 0.0341(8) 0.0281(8) -0.0100(6) 0.0017(6) -0.0077(6) C7 0.0246(7) 0.0248(7) 0.0305(8) -0.0069(6) -0.0056(6) -0.0010(6) C8 0.0198(6) 0.0233(7) 0.0257(7) -0.0037(5) -0.0023(5) -0.0077(5) C9 0.0253(7) 0.0254(7) 0.0223(7) -0.0014(5) -0.0040(5) -0.0069(6) C10 0.0251(7) 0.0224(7) 0.0319(8) -0.0008(6) -0.0035(6) -0.0054(5) C11 0.0343(8) 0.0331(8) 0.0235(7) -0.0027(6) -0.0037(6) -0.0113(6) C12 0.0286(7) 0.0260(7) 0.0263(7) 0.0004(6) -0.0065(6) -0.0057(6) C13 0.0240(7) 0.0330(8) 0.0220(7) -0.0023(6) -0.0043(6) -0.0055(6) C14 0.0230(7) 0.0244(7) 0.0238(7) 0.0008(5) -0.0033(5) -0.0053(5) C15 0.0211(6) 0.0228(7) 0.0244(7) 0.0012(5) -0.0030(5) -0.0057(5) C16 0.0286(7) 0.0322(8) 0.0290(8) -0.0011(6) -0.0076(6) -0.0105(6) C17 0.0245(7) 0.0342(8) 0.0455(9) -0.0023(7) -0.0077(7) -0.0126(6) C18 0.0247(7) 0.0322(8) 0.0419(9) -0.0002(7) 0.0033(6) -0.0113(6) C19 0.0276(7) 0.0308(8) 0.0267(7) -0.0013(6) 0.0011(6) -0.0069(6) C20 0.0197(6) 0.0204(6) 0.0217(7) -0.0007(5) -0.0021(5) -0.0056(5) C21 0.0193(6) 0.0195(6) 0.0217(7) -0.0020(5) -0.0009(5) -0.0046(5) C22 0.0251(7) 0.0258(7) 0.0213(7) 0.0006(5) -0.0032(5) -0.0058(6) C23 0.0238(7) 0.0218(7) 0.0307(8) 0.0040(6) -0.0044(6) -0.0028(5) C24 0.0232(7) 0.0196(7) 0.0328(8) -0.0046(6) 0.0001(6) -0.0023(5) C25 0.0252(7) 0.0237(7) 0.0228(7) -0.0049(5) -0.0002(5) -0.0055(5) C26 0.0223(7) 0.0229(7) 0.0215(7) -0.0043(5) -0.0022(5) -0.0043(5) _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 C15 1.7984(15) . ? S1 S2 2.0556(8) . ? S2 C20 1.7958(15) . ? O1 C13 1.3151(19) . ? O1 H1O 0.8400(2) . ? O2 C13 1.2157(19) . ? O3 C26 1.2713(18) . ? O4 C26 1.2502(18) . ? O5 H1W 0.8400(3) . ? O5 H2W 0.8400(3) . ? O6 H3W 0.8400(2) . ? O6 H4W 0.8400(3) . ? N1 C1 1.337(2) . ? N1 C5 1.341(2) . ? N2 C10 1.342(2) . ? N2 C11 1.344(2) . ? N2 H2N 0.8800(4) . ? C1 C2 1.379(2) . ? C1 H1 0.9500 . ? C2 C3 1.393(2) . ? C2 H2 0.9500 . ? C3 C4 1.393(2) . ? C3 C6 1.512(2) . ? C4 C5 1.385(2) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.527(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.505(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.392(2) . ? C8 C12 1.403(2) . ? C9 C10 1.382(2) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.368(2) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.490(2) . ? C14 C19 1.404(2) . ? C14 C15 1.409(2) . ? C15 C16 1.401(2) . ? C16 C17 1.389(2) . ? C16 H16 0.9500 . ? C17 C18 1.387(2) . ? C17 H17 0.9500 . ? C18 C19 1.383(2) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C25 1.398(2) . ? C20 C21 1.4116(19) . ? C21 C22 1.398(2) . ? C21 C26 1.5101(19) . ? C22 C23 1.390(2) . ? C22 H22 0.9500 . ? C23 C24 1.389(2) . ? C23 H23 0.9500 . ? C24 C25 1.390(2) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? 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 C15 S1 S2 104.50(6) . . ? C20 S2 S1 105.29(5) . . ? C13 O1 H1O 114.4(17) . . ? H1W O5 H2W 110.4(11) . . ? H3W O6 H4W 109.0(11) . . ? C1 N1 C5 117.20(14) . . ? C10 N2 C11 121.53(13) . . ? C10 N2 H2N 119.6(13) . . ? C11 N2 H2N 118.8(13) . . ? N1 C1 C2 123.37(15) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C1 C2 C3 119.69(15) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C2 C3 C4 116.96(14) . . ? C2 C3 C6 120.20(14) . . ? C4 C3 C6 122.72(14) . . ? C5 C4 C3 119.60(14) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? N1 C5 C4 123.08(15) . . ? N1 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? C3 C6 C7 116.47(13) . . ? C3 C6 H6A 108.2 . . ? C7 C6 H6A 108.2 . . ? C3 C6 H6B 108.2 . . ? C7 C6 H6B 108.2 . . ? H6A C6 H6B 107.3 . . ? C8 C7 C6 116.95(13) . . ? C8 C7 H7A 108.1 . . ? C6 C7 H7A 108.1 . . ? C8 C7 H7B 108.1 . . ? C6 C7 H7B 108.1 . . ? H7A C7 H7B 107.3 . . ? C9 C8 C12 117.72(13) . . ? C9 C8 C7 124.05(13) . . ? C12 C8 C7 118.22(13) . . ? C10 C9 C8 119.93(14) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? N2 C10 C9 120.28(14) . . ? N2 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? N2 C11 C12 120.26(14) . . ? N2 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C8 120.27(14) . . ? C11 C12 H12 119.9 . . ? C8 C12 H12 119.9 . . ? O2 C13 O1 124.09(14) . . ? O2 C13 C14 122.29(13) . . ? O1 C13 C14 113.60(13) . . ? C19 C14 C15 119.60(13) . . ? C19 C14 C13 118.83(13) . . ? C15 C14 C13 121.49(13) . . ? C16 C15 C14 118.98(13) . . ? C16 C15 S1 121.40(11) . . ? C14 C15 S1 119.63(11) . . ? C17 C16 C15 120.21(15) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C18 C17 C16 120.93(14) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C19 C18 C17 119.44(14) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C18 C19 C14 120.74(14) . . ? C18 C19 H19 119.6 . . ? C14 C19 H19 119.6 . . ? C25 C20 C21 119.37(13) . . ? C25 C20 S2 121.14(11) . . ? C21 C20 S2 119.47(10) . . ? C22 C21 C20 119.23(13) . . ? C22 C21 C26 118.34(12) . . ? C20 C21 C26 122.43(12) . . ? C23 C22 C21 121.07(13) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C24 C23 C22 119.34(13) . . ? C24 C23 H23 120.3 . . ? C22 C23 H23 120.3 . . ? C23 C24 C25 120.67(13) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C24 C25 C20 120.31(13) . . ? C24 C25 H25 119.8 . . ? C20 C25 H25 119.8 . . ? O4 C26 O3 124.81(13) . . ? O4 C26 C21 118.53(12) . . ? O3 C26 C21 116.66(12) . . ? 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 C15 S1 S2 C20 -88.38(7) . . . . ? C5 N1 C1 C2 -1.5(2) . . . . ? N1 C1 C2 C3 -1.4(3) . . . . ? C1 C2 C3 C4 3.2(2) . . . . ? C1 C2 C3 C6 -172.84(14) . . . . ? C2 C3 C4 C5 -2.2(2) . . . . ? C6 C3 C4 C5 173.73(14) . . . . ? C1 N1 C5 C4 2.6(2) . . . . ? C3 C4 C5 N1 -0.7(2) . . . . ? C2 C3 C6 C7 -144.23(14) . . . . ? C4 C3 C6 C7 40.0(2) . . . . ? C3 C6 C7 C8 69.70(18) . . . . ? C6 C7 C8 C9 -0.5(2) . . . . ? C6 C7 C8 C12 178.67(13) . . . . ? C12 C8 C9 C10 -0.4(2) . . . . ? C7 C8 C9 C10 178.77(13) . . . . ? C11 N2 C10 C9 0.5(2) . . . . ? C8 C9 C10 N2 -0.4(2) . . . . ? C10 N2 C11 C12 0.1(2) . . . . ? N2 C11 C12 C8 -0.9(2) . . . . ? C9 C8 C12 C11 1.0(2) . . . . ? C7 C8 C12 C11 -178.19(14) . . . . ? O2 C13 C14 C19 174.38(15) . . . . ? O1 C13 C14 C19 -4.0(2) . . . . ? O2 C13 C14 C15 -2.5(2) . . . . ? O1 C13 C14 C15 179.12(14) . . . . ? C19 C14 C15 C16 -2.5(2) . . . . ? C13 C14 C15 C16 174.33(13) . . . . ? C19 C14 C15 S1 178.17(11) . . . . ? C13 C14 C15 S1 -5.02(19) . . . . ? S2 S1 C15 C16 10.86(13) . . . . ? S2 S1 C15 C14 -169.80(10) . . . . ? C14 C15 C16 C17 -0.2(2) . . . . ? S1 C15 C16 C17 179.15(12) . . . . ? C15 C16 C17 C18 2.1(2) . . . . ? C16 C17 C18 C19 -1.2(2) . . . . ? C17 C18 C19 C14 -1.5(2) . . . . ? C15 C14 C19 C18 3.4(2) . . . . ? C13 C14 C19 C18 -173.53(14) . . . . ? S1 S2 C20 C25 14.66(12) . . . . ? S1 S2 C20 C21 -163.82(10) . . . . ? C25 C20 C21 C22 -1.0(2) . . . . ? S2 C20 C21 C22 177.48(10) . . . . ? C25 C20 C21 C26 179.35(12) . . . . ? S2 C20 C21 C26 -2.15(18) . . . . ? C20 C21 C22 C23 1.1(2) . . . . ? C26 C21 C22 C23 -179.24(13) . . . . ? C21 C22 C23 C24 -0.5(2) . . . . ? C22 C23 C24 C25 -0.2(2) . . . . ? C23 C24 C25 C20 0.3(2) . . . . ? C21 C20 C25 C24 0.3(2) . . . . ? S2 C20 C25 C24 -178.14(11) . . . . ? C22 C21 C26 O4 152.66(14) . . . . ? C20 C21 C26 O4 -27.7(2) . . . . ? C22 C21 C26 O3 -27.48(19) . . . . ? C20 C21 C26 O3 152.16(14) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.5 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.31 _refine_diff_density_min -0.22 _refine_diff_density_rms 0.044 # Attachment '5.CIF' data_[(HO2C)C6H4SSC6H4(CO2)].[4,4'-bipyridineH]0.5.H2O(5) _database_code_depnum_ccdc_archive 'CCDC 648107' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H16 N O5 S2' _chemical_formula_sum 'C19 H16 N O5 S2' _chemical_formula_weight 402.45 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 7.8072(16) _cell_length_b 11.128(2) _cell_length_c 11.413(2) _cell_angle_alpha 64.69(3) _cell_angle_beta 82.89(3) _cell_angle_gamma 77.70(3) _cell_volume 875.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2635 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 30.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 418 _exptl_absorpt_coefficient_mu 0.337 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.935 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC12\K/SATURN724 _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% '< 1' _diffrn_reflns_number 17318 _diffrn_reflns_av_R_equivalents 0.063 _diffrn_reflns_av_sigmaI/netI 0.046 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.1 _diffrn_reflns_theta_max 26.5 _reflns_number_total 3631 _reflns_number_gt 3334 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) & DIAMOND (Crystal Impact, 2006)' _computing_publication_material SHELXL97 _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^)+(0.0233P)^2^+0.9663P] 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 3631 _refine_ls_number_parameters 256 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.069 _refine_ls_R_factor_gt 0.061 _refine_ls_wR_factor_ref 0.112 _refine_ls_wR_factor_gt 0.109 _refine_ls_goodness_of_fit_ref 1.20 _refine_ls_restrained_S_all 1.19 _refine_ls_shift/su_max <0.001 _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 0.51983(9) 0.19895(7) 0.26541(7) 0.02716(18) Uani 1 1 d . . . S2 S 0.62252(9) 0.00385(7) 0.28849(7) 0.02703(18) Uani 1 1 d . . . O1 O 0.1375(3) 0.5791(2) 0.1082(2) 0.0397(5) Uani 1 1 d D . . H1O H 0.093(5) 0.605(4) 0.166(3) 0.060 Uiso 1 1 d D . . O2 O 0.2969(3) 0.4156(2) 0.2687(2) 0.0406(6) Uani 1 1 d . . . O3 O 0.9871(3) -0.35278(19) 0.2879(2) 0.0340(5) Uani 1 1 d . . . O4 O 0.7352(3) -0.24638(19) 0.3401(2) 0.0321(5) Uani 1 1 d . . . O5 O 0.6627(3) 0.5311(2) 0.5260(2) 0.0338(5) Uani 1 1 d D . . H1W H 0.697(4) 0.526(3) 0.5954(14) 0.051 Uiso 1 1 d D . . H2W H 0.691(4) 0.598(2) 0.4621(17) 0.051 Uiso 1 1 d D . . N1 N 0.7833(3) 0.3103(2) 0.5003(2) 0.0290(5) Uani 1 1 d D . . H1N H 0.734(4) 0.3861(18) 0.507(3) 0.044 Uiso 1 1 d D . . C1 C 0.9464(4) 0.2998(3) 0.4499(3) 0.0301(6) Uani 1 1 d . . . H1 H 1.0027 0.3763 0.4153 0.036 Uiso 1 1 calc R . . C2 C 1.0345(4) 0.1799(3) 0.4470(3) 0.0298(6) Uani 1 1 d . . . H2 H 1.1502 0.1744 0.4100 0.036 Uiso 1 1 calc R . . C3 C 0.9538(3) 0.0661(3) 0.4986(3) 0.0230(6) Uani 1 1 d . . . C4 C 0.7822(4) 0.0824(3) 0.5477(3) 0.0295(6) Uani 1 1 d . . . H4 H 0.7212 0.0085 0.5815 0.035 Uiso 1 1 calc R . . C5 C 0.7005(4) 0.2049(3) 0.5475(3) 0.0324(7) Uani 1 1 d . . . H5 H 0.5835 0.2146 0.5815 0.039 Uiso 1 1 calc R . . C6 C 0.2529(4) 0.4675(3) 0.1563(3) 0.0274(6) Uani 1 1 d . . . C7 C 0.3237(3) 0.4060(3) 0.0641(3) 0.0240(6) Uani 1 1 d . . . C8 C 0.4445(3) 0.2835(3) 0.1030(3) 0.0233(6) Uani 1 1 d . . . C9 C 0.5046(4) 0.2295(3) 0.0124(3) 0.0286(6) Uani 1 1 d . . . H9 H 0.5867 0.1472 0.0373 0.034 Uiso 1 1 calc R . . C10 C 0.4466(4) 0.2939(3) -0.1134(3) 0.0330(7) Uani 1 1 d . . . H10 H 0.4886 0.2551 -0.1735 0.040 Uiso 1 1 calc R . . C11 C 0.3282(4) 0.4140(3) -0.1520(3) 0.0353(7) Uani 1 1 d . . . H11 H 0.2888 0.4580 -0.2383 0.042 Uiso 1 1 calc R . . C12 C 0.2677(4) 0.4694(3) -0.0638(3) 0.0314(7) Uani 1 1 d . . . H12 H 0.1866 0.5522 -0.0903 0.038 Uiso 1 1 calc R . . C13 C 0.8412(3) 0.0061(3) 0.2187(3) 0.0228(6) Uani 1 1 d . . . C14 C 0.9469(3) -0.1141(3) 0.2209(3) 0.0233(6) Uani 1 1 d . . . C15 C 1.1156(4) -0.1095(3) 0.1639(3) 0.0288(6) Uani 1 1 d . . . H15 H 1.1875 -0.1902 0.1646 0.035 Uiso 1 1 calc R . . C16 C 1.1804(4) 0.0101(3) 0.1062(3) 0.0324(7) Uani 1 1 d . . . H16 H 1.2961 0.0111 0.0689 0.039 Uiso 1 1 calc R . . C17 C 1.0755(4) 0.1275(3) 0.1033(3) 0.0306(7) Uani 1 1 d . . . H17 H 1.1188 0.2100 0.0628 0.037 Uiso 1 1 calc R . . C18 C 0.9066(4) 0.1264(3) 0.1591(3) 0.0266(6) Uani 1 1 d . . . H18 H 0.8355 0.2082 0.1565 0.032 Uiso 1 1 calc R . . C19 C 0.8861(4) -0.2480(3) 0.2863(3) 0.0248(6) 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 0.0292(4) 0.0223(4) 0.0270(4) -0.0109(3) -0.0002(3) 0.0026(3) S2 0.0236(4) 0.0203(3) 0.0331(4) -0.0102(3) 0.0040(3) -0.0002(3) O1 0.0428(13) 0.0301(12) 0.0425(14) -0.0193(10) -0.0062(10) 0.0131(10) O2 0.0509(14) 0.0319(12) 0.0344(13) -0.0173(10) -0.0052(10) 0.0119(10) O3 0.0348(11) 0.0212(10) 0.0433(13) -0.0154(9) 0.0006(9) 0.0039(9) O4 0.0274(11) 0.0227(10) 0.0424(12) -0.0122(9) 0.0036(9) -0.0025(8) O5 0.0392(12) 0.0266(11) 0.0372(12) -0.0145(10) -0.0013(10) -0.0063(9) N1 0.0351(14) 0.0200(12) 0.0318(13) -0.0121(11) -0.0007(11) -0.0017(10) C1 0.0339(16) 0.0225(14) 0.0315(16) -0.0087(12) -0.0001(13) -0.0059(12) C2 0.0288(15) 0.0231(14) 0.0345(16) -0.0110(13) 0.0031(12) -0.0032(12) C3 0.0241(13) 0.0235(14) 0.0206(13) -0.0086(11) -0.0023(10) -0.0031(11) C4 0.0300(15) 0.0250(15) 0.0352(16) -0.0143(13) 0.0013(13) -0.0059(12) C5 0.0303(16) 0.0285(16) 0.0402(18) -0.0172(14) 0.0009(13) -0.0036(13) C6 0.0245(14) 0.0172(13) 0.0383(17) -0.0105(13) 0.0008(12) -0.0027(11) C7 0.0213(13) 0.0203(13) 0.0304(15) -0.0101(12) 0.0015(11) -0.0057(11) C8 0.0199(13) 0.0221(14) 0.0268(14) -0.0096(12) 0.0003(11) -0.0034(11) C9 0.0228(14) 0.0289(15) 0.0345(16) -0.0160(13) 0.0002(12) 0.0001(12) C10 0.0286(15) 0.0427(18) 0.0310(17) -0.0203(15) -0.0001(12) -0.0026(13) C11 0.0348(16) 0.0401(18) 0.0278(16) -0.0108(14) -0.0057(13) -0.0046(14) C12 0.0284(15) 0.0259(15) 0.0372(17) -0.0108(13) -0.0061(13) -0.0013(12) C13 0.0222(13) 0.0218(13) 0.0236(14) -0.0098(11) -0.0034(11) -0.0001(11) C14 0.0248(14) 0.0225(14) 0.0220(14) -0.0097(11) -0.0025(11) -0.0010(11) C15 0.0225(14) 0.0306(15) 0.0339(16) -0.0174(13) -0.0031(12) 0.0039(12) C16 0.0241(14) 0.0360(17) 0.0368(17) -0.0159(14) 0.0055(12) -0.0068(12) C17 0.0283(15) 0.0271(15) 0.0341(17) -0.0100(13) -0.0012(12) -0.0060(12) C18 0.0269(14) 0.0205(14) 0.0308(15) -0.0107(12) -0.0009(12) -0.0010(11) C19 0.0271(14) 0.0223(14) 0.0259(15) -0.0116(12) -0.0060(11) 0.0001(11) _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 C8 1.791(3) . ? S1 S2 2.0609(11) . ? S2 C13 1.793(3) . ? O1 C6 1.311(3) . ? O1 H1O 0.8400(11) . ? O2 C6 1.220(4) . ? O3 C19 1.255(3) . ? O4 C19 1.260(3) . ? O5 H1W 0.8400(11) . ? O5 H2W 0.8401(11) . ? N1 C1 1.334(4) . ? N1 C5 1.334(4) . ? N1 H1N 0.8801(11) . ? C1 C2 1.376(4) . ? C1 H1 0.9500 . ? C2 C3 1.400(4) . ? C2 H2 0.9500 . ? C3 C4 1.392(4) . ? C3 C3 1.482(5) 2_756 ? C4 C5 1.376(4) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.480(4) . ? C7 C12 1.402(4) . ? C7 C8 1.408(4) . ? C8 C9 1.394(4) . ? C9 C10 1.388(4) . ? C9 H9 0.9500 . ? C10 C11 1.380(4) . ? C10 H10 0.9500 . ? C11 C12 1.381(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C18 1.394(4) . ? C13 C14 1.406(4) . ? C14 C15 1.396(4) . ? C14 C19 1.505(4) . ? C15 C16 1.384(4) . ? C15 H15 0.9500 . ? C16 C17 1.375(4) . ? C16 H16 0.9500 . ? C17 C18 1.392(4) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? 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 C8 S1 S2 104.88(10) . . ? C13 S2 S1 106.31(10) . . ? C6 O1 H1O 111(3) . . ? H1W O5 H2W 111.2(12) . . ? C1 N1 C5 120.6(3) . . ? C1 N1 H1N 119(2) . . ? C5 N1 H1N 121(2) . . ? N1 C1 C2 121.0(3) . . ? N1 C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? C1 C2 C3 120.1(3) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 116.9(3) . . ? C4 C3 C3 121.3(3) . 2_756 ? C2 C3 C3 121.8(3) . 2_756 ? C5 C4 C3 120.4(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? N1 C5 C4 120.9(3) . . ? N1 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? O2 C6 O1 123.3(3) . . ? O2 C6 C7 121.9(2) . . ? O1 C6 C7 114.7(3) . . ? C12 C7 C8 119.2(3) . . ? C12 C7 C6 119.6(2) . . ? C8 C7 C6 121.2(3) . . ? C9 C8 C7 118.6(3) . . ? C9 C8 S1 120.6(2) . . ? C7 C8 S1 120.8(2) . . ? C10 C9 C8 121.1(3) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C11 C10 C9 120.5(3) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 119.2(3) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C11 C12 C7 121.4(3) . . ? C11 C12 H12 119.3 . . ? C7 C12 H12 119.3 . . ? C18 C13 C14 119.4(2) . . ? C18 C13 S2 120.8(2) . . ? C14 C13 S2 119.8(2) . . ? C15 C14 C13 118.8(3) . . ? C15 C14 C19 119.1(2) . . ? C13 C14 C19 122.1(2) . . ? C16 C15 C14 121.5(3) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C17 C16 C15 119.3(3) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C18 120.6(3) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C13 C18 C17 120.3(3) . . ? C13 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? O3 C19 O4 124.3(3) . . ? O3 C19 C14 119.6(2) . . ? O4 C19 C14 116.1(2) . . ? 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 C8 S1 S2 C13 82.45(13) . . . . ? C5 N1 C1 C2 -1.1(4) . . . . ? N1 C1 C2 C3 -0.6(5) . . . . ? C1 C2 C3 C4 1.9(4) . . . . ? C1 C2 C3 C3 -177.9(3) . . . 2_756 ? C2 C3 C4 C5 -1.7(4) . . . . ? C3 C3 C4 C5 178.1(3) 2_756 . . . ? C1 N1 C5 C4 1.3(5) . . . . ? C3 C4 C5 N1 0.1(5) . . . . ? O2 C6 C7 C12 179.6(3) . . . . ? O1 C6 C7 C12 1.1(4) . . . . ? O2 C6 C7 C8 0.6(4) . . . . ? O1 C6 C7 C8 -177.9(2) . . . . ? C12 C7 C8 C9 0.1(4) . . . . ? C6 C7 C8 C9 179.1(2) . . . . ? C12 C7 C8 S1 179.9(2) . . . . ? C6 C7 C8 S1 -1.1(4) . . . . ? S2 S1 C8 C9 -18.2(2) . . . . ? S2 S1 C8 C7 161.9(2) . . . . ? C7 C8 C9 C10 -0.4(4) . . . . ? S1 C8 C9 C10 179.7(2) . . . . ? C8 C9 C10 C11 0.4(4) . . . . ? C9 C10 C11 C12 -0.1(5) . . . . ? C10 C11 C12 C7 -0.2(5) . . . . ? C8 C7 C12 C11 0.2(4) . . . . ? C6 C7 C12 C11 -178.8(3) . . . . ? S1 S2 C13 C18 -2.4(2) . . . . ? S1 S2 C13 C14 179.3(2) . . . . ? C18 C13 C14 C15 0.5(4) . . . . ? S2 C13 C14 C15 178.8(2) . . . . ? C18 C13 C14 C19 178.6(2) . . . . ? S2 C13 C14 C19 -3.1(4) . . . . ? C13 C14 C15 C16 0.3(4) . . . . ? C19 C14 C15 C16 -177.9(3) . . . . ? C14 C15 C16 C17 -1.0(5) . . . . ? C15 C16 C17 C18 0.8(5) . . . . ? C14 C13 C18 C17 -0.6(4) . . . . ? S2 C13 C18 C17 -178.9(2) . . . . ? C16 C17 C18 C13 -0.1(4) . . . . ? C15 C14 C19 O3 -0.4(4) . . . . ? C13 C14 C19 O3 -178.5(3) . . . . ? C15 C14 C19 O4 177.5(3) . . . . ? C13 C14 C19 O4 -0.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.5 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.26 _refine_diff_density_min -0.30 _refine_diff_density_rms 0.061 # Attachment '6.CIF' data_[(HO2C)C6H4SSC6H4(CO2)].[4,4'-bipyridineH]0.5(6) _database_code_depnum_ccdc_archive 'CCDC 648108' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H30 N2 O8 S4' _chemical_formula_sum 'C40 H30 N2 O8 S4' _chemical_formula_weight 794.90 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.512(3) _cell_length_b 7.8294(13) _cell_length_c 23.312(4) _cell_angle_alpha 90 _cell_angle_beta 102.726(4) _cell_angle_gamma 90 _cell_volume 3473.7(10) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 6295 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 27.4 _exptl_crystal_description block _exptl_crystal_colour tan _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1648 _exptl_absorpt_coefficient_mu 0.335 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.899 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC12\K/SATURN724 _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% '< 1' _diffrn_reflns_number 32402 _diffrn_reflns_av_R_equivalents 0.043 _diffrn_reflns_av_sigmaI/netI 0.027 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 27.5 _reflns_number_total 3883 _reflns_number_gt 3535 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) & DIAMOND (Crystal Impact, 2006)' _computing_publication_material SHELXL97 _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^)+(0.0393P)^2^+4.5259P] 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 3883 _refine_ls_number_parameters 253 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.048 _refine_ls_R_factor_gt 0.042 _refine_ls_wR_factor_ref 0.095 _refine_ls_wR_factor_gt 0.092 _refine_ls_goodness_of_fit_ref 1.12 _refine_ls_restrained_S_all 1.12 _refine_ls_shift/su_max <0.001 _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 0.08392(2) -0.01112(6) 0.621691(19) 0.02050(12) Uani 1 1 d . . . S2 S 0.10450(2) -0.04878(6) 0.540052(18) 0.02084(12) Uani 1 1 d . . . O1 O 0.05250(7) 0.03664(18) 0.72835(6) 0.0294(3) Uani 1 1 d D . . H1O H 0.0185(18) 0.047(6) 0.745(2) 0.044 Uiso 0.50 1 d PD . . O2 O 0.09431(7) 0.25460(19) 0.78597(6) 0.0299(3) Uani 1 1 d . . . O3 O 0.15134(8) -0.34553(18) 0.39277(5) 0.0274(3) Uani 1 1 d D . . H3O H 0.1346(12) -0.297(3) 0.3605(5) 0.041 Uiso 1 1 d D . . O4 O 0.11168(8) -0.10903(17) 0.42832(6) 0.0284(3) Uani 1 1 d . . . N1 N -0.01117(8) -0.3332(2) 0.69028(6) 0.0213(3) Uani 1 1 d D . . H1N H -0.007(2) -0.309(5) 0.7278(5) 0.032 Uiso 0.50 1 d PD . . C1 C -0.04723(9) -0.2331(2) 0.64770(8) 0.0214(4) Uani 1 1 d . . . H1 H -0.0702 -0.1344 0.6580 0.026 Uiso 1 1 calc R . . C2 C -0.05186(9) -0.2699(2) 0.58905(8) 0.0202(4) Uani 1 1 d . . . H2 H -0.0791 -0.1989 0.5596 0.024 Uiso 1 1 calc R . . C3 C -0.01669(9) -0.4109(2) 0.57298(8) 0.0203(4) Uani 1 1 d . . . C4 C 0.01963(10) -0.5148(2) 0.61824(8) 0.0246(4) Uani 1 1 d . . . H4 H 0.0431 -0.6144 0.6094 0.030 Uiso 1 1 calc R . . C5 C 0.02117(11) -0.4720(2) 0.67598(8) 0.0261(4) Uani 1 1 d . . . H5 H 0.0460 -0.5436 0.7065 0.031 Uiso 1 1 calc R . . C6 C -0.01852(9) -0.4417(2) 0.51049(8) 0.0211(4) Uani 1 1 d . . . H6 H -0.0490 -0.3717 0.4827 0.025 Uiso 1 1 calc R . . C7 C 0.09924(10) 0.1490(2) 0.74766(7) 0.0210(4) Uani 1 1 d . . . C8 C 0.16272(9) 0.1478(2) 0.72088(7) 0.0186(4) Uani 1 1 d . . . C9 C 0.16328(9) 0.0745(2) 0.66582(7) 0.0175(3) Uani 1 1 d . . . C10 C 0.22618(9) 0.0696(2) 0.64698(8) 0.0200(4) Uani 1 1 d . . . H10 H 0.2272 0.0199 0.6100 0.024 Uiso 1 1 calc R . . C11 C 0.28731(10) 0.1361(2) 0.68140(8) 0.0226(4) Uani 1 1 d . . . H11 H 0.3300 0.1292 0.6683 0.027 Uiso 1 1 calc R . . C12 C 0.28659(10) 0.2124(2) 0.73468(8) 0.0239(4) Uani 1 1 d . . . H12 H 0.3283 0.2603 0.7579 0.029 Uiso 1 1 calc R . . C13 C 0.22436(10) 0.2182(2) 0.75391(8) 0.0220(4) Uani 1 1 d . . . H13 H 0.2237 0.2714 0.7904 0.026 Uiso 1 1 calc R . . C14 C 0.14933(9) -0.2496(2) 0.54549(7) 0.0183(4) Uani 1 1 d . . . C15 C 0.16330(9) -0.3273(2) 0.49490(7) 0.0179(4) Uani 1 1 d . . . C16 C 0.19870(10) -0.4834(2) 0.50014(8) 0.0233(4) Uani 1 1 d . . . H16 H 0.2082 -0.5358 0.4660 0.028 Uiso 1 1 calc R . . C17 C 0.22013(11) -0.5634(2) 0.55382(9) 0.0282(4) Uani 1 1 d . . . H17 H 0.2444 -0.6692 0.5567 0.034 Uiso 1 1 calc R . . C18 C 0.20578(11) -0.4873(2) 0.60344(8) 0.0257(4) Uani 1 1 d . . . H18 H 0.2199 -0.5419 0.6406 0.031 Uiso 1 1 calc R . . C19 C 0.17096(10) -0.3323(2) 0.59931(8) 0.0225(4) Uani 1 1 d . . . H19 H 0.1617 -0.2814 0.6338 0.027 Uiso 1 1 calc R . . C20 C 0.13953(9) -0.2478(2) 0.43593(8) 0.0194(4) 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 0.0200(2) 0.0252(2) 0.0172(2) -0.00532(17) 0.00602(17) -0.00133(18) S2 0.0259(3) 0.0220(2) 0.0148(2) -0.00158(16) 0.00466(17) 0.00472(18) O1 0.0318(8) 0.0310(8) 0.0312(8) -0.0091(6) 0.0190(6) -0.0068(6) O2 0.0322(8) 0.0386(8) 0.0191(7) -0.0096(6) 0.0064(6) 0.0073(6) O3 0.0418(8) 0.0265(7) 0.0155(6) 0.0002(5) 0.0097(6) 0.0077(6) O4 0.0415(8) 0.0241(7) 0.0191(6) -0.0003(5) 0.0058(6) 0.0099(6) N1 0.0291(8) 0.0215(8) 0.0154(7) -0.0014(6) 0.0095(6) -0.0034(6) C1 0.0242(9) 0.0206(9) 0.0212(9) -0.0008(7) 0.0090(7) -0.0032(7) C2 0.0220(9) 0.0209(9) 0.0176(8) 0.0015(7) 0.0039(7) -0.0015(7) C3 0.0207(9) 0.0232(9) 0.0179(8) -0.0026(7) 0.0061(7) -0.0055(7) C4 0.0311(10) 0.0231(9) 0.0214(9) -0.0007(7) 0.0092(8) 0.0042(8) C5 0.0342(11) 0.0258(10) 0.0190(9) 0.0034(7) 0.0078(8) 0.0021(8) C6 0.0226(9) 0.0235(9) 0.0173(8) -0.0010(7) 0.0049(7) -0.0036(7) C7 0.0279(10) 0.0211(9) 0.0146(8) 0.0027(7) 0.0058(7) 0.0057(7) C8 0.0250(9) 0.0150(8) 0.0162(8) 0.0016(6) 0.0053(7) 0.0030(7) C9 0.0216(9) 0.0138(8) 0.0171(8) 0.0009(6) 0.0045(7) 0.0009(7) C10 0.0249(9) 0.0176(8) 0.0187(8) -0.0016(7) 0.0072(7) -0.0010(7) C11 0.0216(9) 0.0186(9) 0.0293(10) -0.0002(7) 0.0092(8) -0.0014(7) C12 0.0240(10) 0.0192(9) 0.0263(10) -0.0005(7) 0.0006(7) -0.0016(7) C13 0.0300(10) 0.0181(9) 0.0169(8) -0.0022(7) 0.0028(7) 0.0020(7) C14 0.0181(9) 0.0178(8) 0.0191(8) -0.0009(7) 0.0044(7) -0.0022(7) C15 0.0182(9) 0.0184(8) 0.0184(8) -0.0015(7) 0.0066(7) -0.0027(7) C16 0.0280(10) 0.0220(9) 0.0221(9) -0.0010(7) 0.0104(8) 0.0001(8) C17 0.0353(11) 0.0195(9) 0.0298(10) 0.0027(8) 0.0068(8) 0.0063(8) C18 0.0336(11) 0.0236(9) 0.0190(9) 0.0036(7) 0.0036(8) 0.0008(8) C19 0.0275(10) 0.0230(9) 0.0165(8) -0.0020(7) 0.0039(7) -0.0016(8) C20 0.0206(9) 0.0201(9) 0.0193(9) -0.0027(7) 0.0081(7) -0.0016(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 C9 1.7899(18) . ? S1 S2 2.0510(7) . ? S2 C14 1.7902(18) . ? O1 C7 1.276(2) . ? O1 H1O 0.8400(11) . ? O2 C7 1.236(2) . ? O3 C20 1.324(2) . ? O3 H3O 0.8400(10) . ? O4 C20 1.210(2) . ? N1 C5 1.335(2) . ? N1 C1 1.337(2) . ? N1 H1N 0.8800(11) . ? C1 C2 1.381(2) . ? C1 H1 0.9500 . ? C2 C3 1.394(3) . ? C2 H2 0.9500 . ? C3 C4 1.396(3) . ? C3 C6 1.469(2) . ? C4 C5 1.381(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C6 1.323(4) 5_546 ? C6 H6 0.9500 . ? C7 C8 1.505(2) . ? C8 C13 1.391(3) . ? C8 C9 1.408(2) . ? C9 C10 1.392(2) . ? C10 C11 1.384(3) . ? C10 H10 0.9500 . ? C11 C12 1.381(3) . ? C11 H11 0.9500 . ? C12 C13 1.385(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C19 1.392(2) . ? C14 C15 1.406(2) . ? C15 C16 1.396(3) . ? C15 C20 1.487(2) . ? C16 C17 1.379(3) . ? C16 H16 0.9500 . ? C17 C18 1.383(3) . ? C17 H17 0.9500 . ? C18 C19 1.384(3) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? 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 S1 S2 105.41(6) . . ? C14 S2 S1 104.66(6) . . ? C7 O1 H1O 110(3) . . ? C20 O3 H3O 108.8(18) . . ? C5 N1 C1 119.50(16) . . ? C5 N1 H1N 119(3) . . ? C1 N1 H1N 122(3) . . ? N1 C1 C2 121.44(17) . . ? N1 C1 H1 119.3 . . ? C2 C1 H1 119.3 . . ? C3 C2 C1 120.19(17) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 117.17(16) . . ? C2 C3 C6 119.38(16) . . ? C4 C3 C6 123.45(17) . . ? C3 C4 C5 119.59(17) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 122.05(18) . . ? N1 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C6 C6 C3 125.7(2) 5_546 . ? C6 C6 H6 117.1 5_546 . ? C3 C6 H6 117.1 . . ? O2 C7 O1 123.54(17) . . ? O2 C7 C8 120.42(17) . . ? O1 C7 C8 116.04(15) . . ? C13 C8 C9 119.12(16) . . ? C13 C8 C7 117.26(15) . . ? C9 C8 C7 123.58(16) . . ? C10 C9 C8 118.90(16) . . ? C10 C9 S1 121.30(13) . . ? C8 C9 S1 119.81(13) . . ? C11 C10 C9 120.90(16) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 120.40(17) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C13 119.26(17) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C8 C13 C12 121.37(16) . . ? C8 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C19 C14 C15 118.60(16) . . ? C19 C14 S2 121.23(14) . . ? C15 C14 S2 120.17(13) . . ? C14 C15 C16 119.27(16) . . ? C14 C15 C20 121.06(16) . . ? C16 C15 C20 119.65(15) . . ? C17 C16 C15 121.46(17) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C18 C17 C16 119.13(18) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C17 C18 C19 120.39(17) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C14 C19 C18 121.15(17) . . ? C14 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? O4 C20 O3 123.72(17) . . ? O4 C20 C15 123.35(16) . . ? O3 C20 C15 112.93(15) . . ? 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 C9 S1 S2 C14 82.21(8) . . . . ? C5 N1 C1 C2 0.0(3) . . . . ? N1 C1 C2 C3 -2.1(3) . . . . ? C1 C2 C3 C4 3.0(3) . . . . ? C1 C2 C3 C6 -176.09(16) . . . . ? C2 C3 C4 C5 -2.0(3) . . . . ? C6 C3 C4 C5 177.08(18) . . . . ? C1 N1 C5 C4 1.1(3) . . . . ? C3 C4 C5 N1 0.0(3) . . . . ? C2 C3 C6 C6 172.0(2) . . . 5_546 ? C4 C3 C6 C6 -7.0(4) . . . 5_546 ? O2 C7 C8 C13 23.8(2) . . . . ? O1 C7 C8 C13 -156.28(17) . . . . ? O2 C7 C8 C9 -158.51(17) . . . . ? O1 C7 C8 C9 21.4(2) . . . . ? C13 C8 C9 C10 2.1(2) . . . . ? C7 C8 C9 C10 -175.51(16) . . . . ? C13 C8 C9 S1 -178.15(13) . . . . ? C7 C8 C9 S1 4.2(2) . . . . ? S2 S1 C9 C10 -13.44(16) . . . . ? S2 S1 C9 C8 166.86(12) . . . . ? C8 C9 C10 C11 -0.3(3) . . . . ? S1 C9 C10 C11 -179.99(14) . . . . ? C9 C10 C11 C12 -1.5(3) . . . . ? C10 C11 C12 C13 1.4(3) . . . . ? C9 C8 C13 C12 -2.3(3) . . . . ? C7 C8 C13 C12 175.54(16) . . . . ? C11 C12 C13 C8 0.5(3) . . . . ? S1 S2 C14 C19 -8.45(16) . . . . ? S1 S2 C14 C15 171.45(13) . . . . ? C19 C14 C15 C16 -0.5(3) . . . . ? S2 C14 C15 C16 179.63(13) . . . . ? C19 C14 C15 C20 178.09(16) . . . . ? S2 C14 C15 C20 -1.8(2) . . . . ? C14 C15 C16 C17 0.1(3) . . . . ? C20 C15 C16 C17 -178.44(17) . . . . ? C15 C16 C17 C18 0.4(3) . . . . ? C16 C17 C18 C19 -0.6(3) . . . . ? C15 C14 C19 C18 0.3(3) . . . . ? S2 C14 C19 C18 -179.84(14) . . . . ? C17 C18 C19 C14 0.3(3) . . . . ? C14 C15 C20 O4 5.2(3) . . . . ? C16 C15 C20 O4 -176.25(17) . . . . ? C14 C15 C20 O3 -174.09(16) . . . . ? C16 C15 C20 O3 4.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.35 _refine_diff_density_min -0.25 _refine_diff_density_rms 0.058 # Attachment '7.CIF' data_[(HO2C)C6H4SSC6H4(CO2)].[1,2-bis(pyridineH)ethane]0.5(7) _database_code_depnum_ccdc_archive 'CCDC 648109' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H16 N O4 S2' _chemical_formula_sum 'C20 H16 N O4 S2' _chemical_formula_weight 398.46 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.734(4) _cell_length_b 7.8916(16) _cell_length_c 23.226(5) _cell_angle_alpha 90 _cell_angle_beta 100.80(3) _cell_angle_gamma 90 _cell_volume 3553.0(13) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7576 _cell_measurement_theta_min 3. _cell_measurement_theta_max 30.7 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1656 _exptl_absorpt_coefficient_mu 0.327 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.833 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC12\K/SATURN724 _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% '< 1' _diffrn_reflns_number 12762 _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_av_sigmaI/netI 0.028 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.2 _diffrn_reflns_theta_max 27.5 _reflns_number_total 4046 _reflns_number_gt 3863 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) & DIAMOND (Crystal Impact, 2006)' _computing_publication_material SHELXL97 _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^)+(0.0347P)^2^+4.5253P] 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 4046 _refine_ls_number_parameters 253 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.041 _refine_ls_R_factor_gt 0.040 _refine_ls_wR_factor_ref 0.094 _refine_ls_wR_factor_gt 0.093 _refine_ls_goodness_of_fit_ref 1.09 _refine_ls_restrained_S_all 1.09 _refine_ls_shift/su_max <0.001 _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 0.41225(2) 0.50108(5) -0.123251(18) 0.02653(11) Uani 1 1 d . . . S2 S 0.38983(2) 0.54004(5) -0.041615(17) 0.02616(11) Uani 1 1 d . . . O1 O 0.44730(7) 0.44633(18) -0.22832(6) 0.0390(3) Uani 1 1 d D . . H1O H 0.4839(16) 0.435(6) -0.241(2) 0.059 Uiso 0.50 1 d PD . . O2 O 0.40570(7) 0.23534(19) -0.28713(6) 0.0423(3) Uani 1 1 d . . . O3 O 0.34991(7) 0.84954(17) 0.10676(5) 0.0364(3) Uani 1 1 d D . . H3O H 0.3677(11) 0.808(3) 0.1394(5) 0.055 Uiso 1 1 d D . . O4 O 0.38667(8) 0.61087(17) 0.07140(6) 0.0403(3) Uani 1 1 d . . . N1 N 0.50985(8) -0.1718(2) -0.19121(6) 0.0314(3) Uani 1 1 d D . . H1N H 0.512(2) -0.183(5) -0.2285(5) 0.047 Uiso 0.50 1 d PD . . C1 C 0.47901(11) -0.0351(2) -0.17431(8) 0.0384(4) Uani 1 1 d . . . H1 H 0.4551 0.0390 -0.2034 0.046 Uiso 1 1 calc R . . C2 C 0.48057(10) 0.0026(2) -0.11587(8) 0.0352(4) Uani 1 1 d . . . H2 H 0.4581 0.1011 -0.1053 0.042 Uiso 1 1 calc R . . C3 C 0.51524(8) -0.1045(2) -0.07286(7) 0.0253(3) Uani 1 1 d . . . C4 C 0.54874(9) -0.2434(2) -0.09173(7) 0.0275(3) Uani 1 1 d . . . H4 H 0.5747 -0.3173 -0.0637 0.033 Uiso 1 1 calc R . . C5 C 0.54464(9) -0.2748(2) -0.15029(8) 0.0290(4) Uani 1 1 d . . . H5 H 0.5670 -0.3719 -0.1621 0.035 Uiso 1 1 calc R . . C6 C 0.51710(9) -0.0804(2) -0.00820(7) 0.0265(3) Uani 1 1 d . . . H6A H 0.5659 -0.0803 0.0122 0.032 Uiso 1 1 calc R . . H6B H 0.4943 -0.1788 0.0065 0.032 Uiso 1 1 calc R . . C7 C 0.40063(9) 0.3386(2) -0.24827(7) 0.0265(3) Uani 1 1 d . . . C8 C 0.33721(8) 0.3418(2) -0.22133(7) 0.0230(3) Uani 1 1 d . . . C9 C 0.33520(8) 0.41503(19) -0.16642(7) 0.0217(3) Uani 1 1 d . . . C10 C 0.27262(9) 0.4213(2) -0.14706(7) 0.0259(3) Uani 1 1 d . . . H10 H 0.2707 0.4721 -0.1103 0.031 Uiso 1 1 calc R . . C11 C 0.21301(9) 0.3545(2) -0.18053(8) 0.0293(4) Uani 1 1 d . . . H11 H 0.1706 0.3616 -0.1669 0.035 Uiso 1 1 calc R . . C12 C 0.21516(9) 0.2777(2) -0.23372(8) 0.0316(4) Uani 1 1 d . . . H12 H 0.1746 0.2297 -0.2564 0.038 Uiso 1 1 calc R . . C13 C 0.27711(9) 0.2716(2) -0.25341(7) 0.0294(4) Uani 1 1 d . . . H13 H 0.2787 0.2182 -0.2898 0.035 Uiso 1 1 calc R . . C14 C 0.34773(8) 0.7423(2) -0.04631(7) 0.0230(3) Uani 1 1 d . . . C15 C 0.33581(8) 0.8237(2) 0.00482(7) 0.0232(3) Uani 1 1 d . . . C16 C 0.30209(9) 0.9801(2) -0.00008(8) 0.0302(4) Uani 1 1 d . . . H16 H 0.2943 1.0357 0.0344 0.036 Uiso 1 1 calc R . . C17 C 0.27979(10) 1.0558(2) -0.05387(9) 0.0359(4) Uani 1 1 d . . . H17 H 0.2561 1.1612 -0.0565 0.043 Uiso 1 1 calc R . . C18 C 0.29236(10) 0.9764(2) -0.10383(8) 0.0350(4) Uani 1 1 d . . . H18 H 0.2779 1.0282 -0.1410 0.042 Uiso 1 1 calc R . . C19 C 0.32592(9) 0.8220(2) -0.10000(7) 0.0290(4) Uani 1 1 d . . . H19 H 0.3343 0.7692 -0.1348 0.035 Uiso 1 1 calc R . . C20 C 0.36019(8) 0.7490(2) 0.06359(7) 0.0257(3) 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 0.0258(2) 0.0315(2) 0.0234(2) -0.00738(16) 0.00746(15) -0.00220(16) S2 0.0337(2) 0.0250(2) 0.0197(2) -0.00266(15) 0.00465(15) 0.00494(16) O1 0.0395(7) 0.0424(8) 0.0419(8) -0.0122(6) 0.0247(6) -0.0078(6) O2 0.0450(8) 0.0551(9) 0.0278(7) -0.0156(6) 0.0095(6) 0.0092(7) O3 0.0557(8) 0.0352(7) 0.0201(6) -0.0005(5) 0.0114(6) 0.0129(6) O4 0.0623(9) 0.0327(7) 0.0255(7) 0.0007(5) 0.0069(6) 0.0171(7) N1 0.0420(8) 0.0318(8) 0.0227(7) 0.0001(6) 0.0116(6) -0.0028(7) C1 0.0541(12) 0.0353(10) 0.0266(9) 0.0052(8) 0.0096(8) 0.0085(9) C2 0.0451(10) 0.0317(9) 0.0300(9) -0.0002(7) 0.0099(8) 0.0098(8) C3 0.0270(7) 0.0263(8) 0.0235(8) -0.0017(6) 0.0067(6) -0.0037(6) C4 0.0296(8) 0.0266(8) 0.0266(8) 0.0000(6) 0.0062(6) -0.0013(7) C5 0.0330(8) 0.0278(8) 0.0283(9) -0.0018(7) 0.0114(7) -0.0015(7) C6 0.0299(8) 0.0281(8) 0.0217(8) -0.0019(6) 0.0056(6) -0.0018(7) C7 0.0342(8) 0.0279(8) 0.0181(7) 0.0024(6) 0.0067(6) 0.0077(7) C8 0.0293(8) 0.0199(7) 0.0202(7) 0.0004(6) 0.0056(6) 0.0023(6) C9 0.0274(7) 0.0178(7) 0.0205(7) 0.0003(6) 0.0058(6) 0.0009(6) C10 0.0310(8) 0.0236(8) 0.0248(8) -0.0031(6) 0.0093(6) -0.0022(7) C11 0.0278(8) 0.0267(8) 0.0346(9) 0.0003(7) 0.0088(7) -0.0018(7) C12 0.0303(8) 0.0295(9) 0.0324(9) -0.0038(7) -0.0009(7) -0.0029(7) C13 0.0380(9) 0.0270(8) 0.0220(8) -0.0043(6) 0.0020(7) 0.0017(7) C14 0.0239(7) 0.0222(7) 0.0231(8) -0.0012(6) 0.0049(6) -0.0016(6) C15 0.0240(7) 0.0237(7) 0.0229(8) -0.0006(6) 0.0072(6) -0.0014(6) C16 0.0346(9) 0.0277(8) 0.0302(9) -0.0011(7) 0.0112(7) 0.0045(7) C17 0.0427(10) 0.0282(9) 0.0366(10) 0.0040(7) 0.0073(8) 0.0104(8) C18 0.0442(10) 0.0321(9) 0.0271(9) 0.0054(7) 0.0025(7) 0.0053(8) C19 0.0357(9) 0.0283(8) 0.0224(8) -0.0009(6) 0.0035(7) 0.0013(7) C20 0.0288(8) 0.0259(8) 0.0242(8) -0.0019(6) 0.0095(6) -0.0006(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 C9 1.7909(17) . ? S1 S2 2.0494(7) . ? S2 C14 1.7935(16) . ? O1 C7 1.275(2) . ? O1 H1O 0.8400(11) . ? O2 C7 1.234(2) . ? O3 C20 1.324(2) . ? O3 H3O 0.8400(11) . ? O4 C20 1.208(2) . ? N1 C1 1.333(2) . ? N1 C5 1.338(2) . ? N1 H1N 0.8800(11) . ? C1 C2 1.384(3) . ? C1 H1 0.9500 . ? C2 C3 1.387(2) . ? C2 H2 0.9500 . ? C3 C4 1.393(2) . ? C3 C6 1.507(2) . ? C4 C5 1.370(2) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C6 1.519(3) 5_655 ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.501(2) . ? C8 C13 1.392(2) . ? C8 C9 1.407(2) . ? C9 C10 1.392(2) . ? C10 C11 1.387(2) . ? C10 H10 0.9500 . ? C11 C12 1.384(2) . ? C11 H11 0.9500 . ? C12 C13 1.384(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C19 1.391(2) . ? C14 C15 1.408(2) . ? C15 C16 1.397(2) . ? C15 C20 1.482(2) . ? C16 C17 1.380(3) . ? C16 H16 0.9500 . ? C17 C18 1.382(3) . ? C17 H17 0.9500 . ? C18 C19 1.381(3) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? 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 S1 S2 105.49(6) . . ? C14 S2 S1 104.78(6) . . ? C7 O1 H1O 114(3) . . ? C20 O3 H3O 110.7(17) . . ? C1 N1 C5 118.93(15) . . ? C1 N1 H1N 119(3) . . ? C5 N1 H1N 122(3) . . ? N1 C1 C2 122.37(17) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C1 C2 C3 119.48(17) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C2 C3 C4 116.89(16) . . ? C2 C3 C6 123.88(15) . . ? C4 C3 C6 119.22(15) . . ? C5 C4 C3 120.76(16) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? N1 C5 C4 121.50(16) . . ? N1 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C3 C6 C6 115.20(18) . 5_655 ? C3 C6 H6A 108.5 . . ? C6 C6 H6A 108.5 5_655 . ? C3 C6 H6B 108.5 . . ? C6 C6 H6B 108.5 5_655 . ? H6A C6 H6B 107.5 . . ? O2 C7 O1 123.66(16) . . ? O2 C7 C8 120.29(16) . . ? O1 C7 C8 116.05(14) . . ? C13 C8 C9 118.86(15) . . ? C13 C8 C7 117.61(14) . . ? C9 C8 C7 123.51(15) . . ? C10 C9 C8 118.98(15) . . ? C10 C9 S1 121.15(12) . . ? C8 C9 S1 119.86(12) . . ? C11 C10 C9 121.08(15) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C12 C11 C10 120.14(16) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C13 C12 C11 119.14(16) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C12 C13 C8 121.74(16) . . ? C12 C13 H13 119.1 . . ? C8 C13 H13 119.1 . . ? C19 C14 C15 118.53(15) . . ? C19 C14 S2 121.26(13) . . ? C15 C14 S2 120.21(12) . . ? C16 C15 C14 119.11(15) . . ? C16 C15 C20 119.61(15) . . ? C14 C15 C20 121.26(14) . . ? C17 C16 C15 121.49(16) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C16 C17 C18 119.14(17) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? C17 C18 C19 120.35(17) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C18 C19 C14 121.37(16) . . ? C18 C19 H19 119.3 . . ? C14 C19 H19 119.3 . . ? O4 C20 O3 123.42(16) . . ? O4 C20 C15 123.64(15) . . ? O3 C20 C15 112.94(14) . . ? 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 C9 S1 S2 C14 -83.86(8) . . . . ? C5 N1 C1 C2 -1.2(3) . . . . ? N1 C1 C2 C3 0.0(3) . . . . ? C1 C2 C3 C4 1.9(3) . . . . ? C1 C2 C3 C6 -176.72(18) . . . . ? C2 C3 C4 C5 -2.7(2) . . . . ? C6 C3 C4 C5 176.05(15) . . . . ? C1 N1 C5 C4 0.5(3) . . . . ? C3 C4 C5 N1 1.5(3) . . . . ? C2 C3 C6 C6 -5.0(3) . . . 5_655 ? C4 C3 C6 C6 176.36(17) . . . 5_655 ? O2 C7 C8 C13 -21.8(2) . . . . ? O1 C7 C8 C13 158.61(16) . . . . ? O2 C7 C8 C9 159.73(16) . . . . ? O1 C7 C8 C9 -19.9(2) . . . . ? C13 C8 C9 C10 -2.6(2) . . . . ? C7 C8 C9 C10 175.82(15) . . . . ? C13 C8 C9 S1 178.29(12) . . . . ? C7 C8 C9 S1 -3.2(2) . . . . ? S2 S1 C9 C10 13.86(14) . . . . ? S2 S1 C9 C8 -167.10(11) . . . . ? C8 C9 C10 C11 1.0(2) . . . . ? S1 C9 C10 C11 -179.98(13) . . . . ? C9 C10 C11 C12 1.0(3) . . . . ? C10 C11 C12 C13 -1.3(3) . . . . ? C11 C12 C13 C8 -0.5(3) . . . . ? C9 C8 C13 C12 2.4(3) . . . . ? C7 C8 C13 C12 -176.13(16) . . . . ? S1 S2 C14 C19 11.53(15) . . . . ? S1 S2 C14 C15 -168.77(11) . . . . ? C19 C14 C15 C16 0.6(2) . . . . ? S2 C14 C15 C16 -179.14(12) . . . . ? C19 C14 C15 C20 -177.56(15) . . . . ? S2 C14 C15 C20 2.7(2) . . . . ? C14 C15 C16 C17 0.5(3) . . . . ? C20 C15 C16 C17 178.68(17) . . . . ? C15 C16 C17 C18 -1.3(3) . . . . ? C16 C17 C18 C19 0.9(3) . . . . ? C17 C18 C19 C14 0.1(3) . . . . ? C15 C14 C19 C18 -0.9(3) . . . . ? S2 C14 C19 C18 178.81(14) . . . . ? C16 C15 C20 O4 176.24(17) . . . . ? C14 C15 C20 O4 -5.6(3) . . . . ? C16 C15 C20 O3 -3.8(2) . . . . ? C14 C15 C20 O3 174.35(15) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.31 _refine_diff_density_min -0.22 _refine_diff_density_rms 0.049 # Attachment '8.CIF' data_[(HO2C)C6H4SSC6H4(CO2)].[1,2-bis(pyridineH)ethane]0.5.EtOH(8) _database_code_depnum_ccdc_archive 'CCDC 648110' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H22 N O5 S2' _chemical_formula_sum 'C22 H22 N O5 S2' _chemical_formula_weight 444.53 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 8.9817(3) _cell_length_b 9.1350(2) _cell_length_c 12.9172(5) _cell_angle_alpha 93.469(2) _cell_angle_beta 90.466(2) _cell_angle_gamma 97.325(2) _cell_volume 1049.12(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4728 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour tan _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 466 _exptl_absorpt_coefficient_mu 0.288 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.809 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 23723 _diffrn_reflns_av_R_equivalents 0.047 _diffrn_reflns_av_sigmaI/netI 0.044 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.5 _diffrn_reflns_theta_max 27.5 _reflns_number_total 4811 _reflns_number_gt 3641 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006' _computing_publication_material SHELXL97 _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^)+(0.1002P)^2^+0.9106P] 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 4811 _refine_ls_number_parameters 275 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.080 _refine_ls_R_factor_gt 0.055 _refine_ls_wR_factor_ref 0.178 _refine_ls_wR_factor_gt 0.157 _refine_ls_goodness_of_fit_ref 1.10 _refine_ls_restrained_S_all 1.10 _refine_ls_shift/su_max <0.001 _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 0.07687(7) 0.81078(7) 0.25046(5) 0.02092(19) Uani 1 1 d . . . S2 S 0.28444(7) 0.93220(7) 0.27406(5) 0.02261(19) Uani 1 1 d . . . O1 O -0.2924(2) 0.4501(2) 0.25756(19) 0.0360(6) Uani 1 1 d . . . O2 O -0.1826(2) 0.6535(2) 0.19026(15) 0.0240(4) Uani 1 1 d . . . O3 O 0.5818(2) 1.3188(2) 0.41021(18) 0.0309(5) Uani 1 1 d D . . H3O H 0.628(4) 1.349(4) 0.3576(19) 0.046 Uiso 1 1 d D . . O4 O 0.5192(2) 1.1464(2) 0.28149(17) 0.0291(5) Uani 1 1 d D . . N1 N -0.5338(3) 0.4807(3) 0.1538(2) 0.0317(6) Uani 1 1 d D . . H1N H -0.456(3) 0.462(4) 0.190(3) 0.048 Uiso 1 1 d D . . C1 C -0.5430(3) 0.6120(4) 0.1152(2) 0.0316(7) Uani 1 1 d . . . H1 H -0.4596 0.6873 0.1218 0.038 Uiso 1 1 calc R . . C2 C -0.6720(3) 0.6386(4) 0.0663(2) 0.0297(6) Uani 1 1 d . . . H2 H -0.6770 0.7316 0.0381 0.036 Uiso 1 1 calc R . . C3 C -0.7953(3) 0.5300(3) 0.0577(2) 0.0245(6) Uani 1 1 d . . . C4 C -0.7823(3) 0.3948(3) 0.0987(3) 0.0313(7) Uani 1 1 d . . . H4 H -0.8645 0.3180 0.0937 0.038 Uiso 1 1 calc R . . C5 C -0.6498(4) 0.3725(4) 0.1464(3) 0.0355(7) Uani 1 1 d . . . H5 H -0.6408 0.2801 0.1743 0.043 Uiso 1 1 calc R . . C6 C -0.9377(3) 0.5646(3) 0.0069(2) 0.0245(6) Uani 1 1 d . . . H6A H -0.9127 0.6017 -0.0621 0.029 Uiso 1 1 calc R . . H6B H -0.9761 0.6454 0.0491 0.029 Uiso 1 1 calc R . . C7 C -0.1787(3) 0.5475(3) 0.2444(2) 0.0210(6) Uani 1 1 d . . . C8 C -0.0346(3) 0.5257(3) 0.2978(2) 0.0201(5) Uani 1 1 d . . . C9 C 0.0901(3) 0.6361(3) 0.3039(2) 0.0196(5) Uani 1 1 d . . . C10 C 0.2203(3) 0.6098(3) 0.3550(2) 0.0239(6) Uani 1 1 d . . . H10 H 0.3044 0.6845 0.3603 0.029 Uiso 1 1 calc R . . C11 C 0.2285(3) 0.4757(3) 0.3982(2) 0.0278(6) Uani 1 1 d . . . H11 H 0.3184 0.4591 0.4324 0.033 Uiso 1 1 calc R . . C12 C 0.1067(3) 0.3657(3) 0.3920(3) 0.0292(7) Uani 1 1 d . . . H12 H 0.1124 0.2738 0.4215 0.035 Uiso 1 1 calc R . . C13 C -0.0235(3) 0.3918(3) 0.3420(2) 0.0259(6) Uani 1 1 d . . . H13 H -0.1073 0.3168 0.3377 0.031 Uiso 1 1 calc R . . C14 C 0.2859(3) 1.0046(3) 0.4063(2) 0.0195(5) Uani 1 1 d . . . C15 C 0.3913(3) 1.1259(3) 0.4409(2) 0.0206(5) Uani 1 1 d . . . C16 C 0.3866(3) 1.1833(3) 0.5434(2) 0.0252(6) Uani 1 1 d . . . H16 H 0.4558 1.2666 0.5662 0.030 Uiso 1 1 calc R . . C17 C 0.2831(3) 1.1212(3) 0.6124(2) 0.0262(6) Uani 1 1 d . . . H17 H 0.2818 1.1606 0.6821 0.031 Uiso 1 1 calc R . . C18 C 0.1819(3) 1.0011(3) 0.5781(2) 0.0247(6) Uani 1 1 d . . . H18 H 0.1107 0.9579 0.6250 0.030 Uiso 1 1 calc R . . C19 C 0.1823(3) 0.9425(3) 0.4766(2) 0.0222(6) Uani 1 1 d . . . H19 H 0.1117 0.8596 0.4547 0.027 Uiso 1 1 calc R . . C20 C 0.5031(3) 1.1963(3) 0.3695(2) 0.0230(6) Uani 1 1 d . . . O5 O 0.7445(7) 1.1636(6) 0.1262(4) 0.1273(19) Uani 1 1 d D . . H5O H 0.695(10) 1.147(11) 0.180(5) 0.191 Uiso 1 1 d D . . C21 C 0.7783(8) 1.0302(7) 0.1194(5) 0.0892(17) Uiso 0.50 1 d P A 1 H21A H 0.6845 0.9615 0.1248 0.107 Uiso 0.50 1 calc PR A 1 H21B H 0.8428 1.0176 0.1799 0.107 Uiso 0.50 1 calc PR A 1 C22 C 0.8532(14) 0.9863(14) 0.0276(10) 0.091(3) Uiso 0.50 1 d P A 1 H22A H 0.8637 0.8808 0.0277 0.136 Uiso 0.50 1 calc PR A 1 H22B H 0.9529 1.0438 0.0257 0.136 Uiso 0.50 1 calc PR A 1 H22C H 0.7945 1.0041 -0.0336 0.136 Uiso 0.50 1 calc PR A 1 C21' C 0.7783(8) 1.0302(7) 0.1194(5) 0.0892(17) Uiso 0.50 1 d P A 2 H21C H 0.7793 0.9844 0.1869 0.107 Uiso 0.50 1 calc PR A 2 H21D H 0.8721 1.0200 0.0814 0.107 Uiso 0.50 1 calc PR A 2 C24 C 0.628(2) 0.977(3) 0.0508(18) 0.183(9) Uiso 0.50 1 d P A 2 H24A H 0.6180 0.8702 0.0359 0.274 Uiso 0.50 1 calc PR A 2 H24B H 0.6339 1.0271 -0.0145 0.274 Uiso 0.50 1 calc PR A 2 H24C H 0.5403 1.0031 0.0893 0.274 Uiso 0.50 1 calc PR A 2 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 0.0179(3) 0.0179(3) 0.0260(4) 0.0014(2) -0.0045(3) -0.0010(2) S2 0.0191(3) 0.0212(3) 0.0256(4) -0.0002(3) -0.0001(3) -0.0040(3) O1 0.0173(10) 0.0350(12) 0.0543(15) 0.0187(10) -0.0145(9) -0.0092(9) O2 0.0185(9) 0.0247(10) 0.0289(11) 0.0046(8) -0.0040(8) 0.0016(8) O3 0.0236(11) 0.0247(10) 0.0412(13) 0.0014(9) -0.0047(9) -0.0087(8) O4 0.0239(10) 0.0257(10) 0.0363(12) 0.0037(9) 0.0025(9) -0.0035(8) N1 0.0170(12) 0.0477(16) 0.0304(14) -0.0007(11) -0.0075(10) 0.0063(11) C1 0.0193(14) 0.0424(18) 0.0317(16) -0.0004(13) -0.0056(12) 0.0001(13) C2 0.0215(14) 0.0361(16) 0.0307(16) 0.0010(12) -0.0051(12) 0.0009(12) C3 0.0174(13) 0.0346(15) 0.0210(14) -0.0033(11) -0.0034(10) 0.0045(11) C4 0.0224(14) 0.0334(16) 0.0373(17) -0.0007(13) -0.0105(13) 0.0022(12) C5 0.0273(16) 0.0386(17) 0.0411(19) 0.0030(14) -0.0093(14) 0.0062(14) C6 0.0194(13) 0.0299(15) 0.0239(14) -0.0016(11) -0.0055(11) 0.0039(12) C7 0.0154(13) 0.0216(13) 0.0254(14) -0.0012(10) -0.0042(10) 0.0020(10) C8 0.0138(12) 0.0209(12) 0.0247(14) -0.0020(10) -0.0035(10) 0.0013(10) C9 0.0164(12) 0.0171(12) 0.0250(14) -0.0017(10) -0.0030(10) 0.0021(10) C10 0.0163(13) 0.0223(13) 0.0321(15) -0.0017(11) -0.0067(11) 0.0001(11) C11 0.0198(14) 0.0259(14) 0.0383(17) 0.0002(12) -0.0110(12) 0.0064(11) C12 0.0232(15) 0.0212(13) 0.0438(18) 0.0054(12) -0.0064(13) 0.0049(11) C13 0.0183(13) 0.0189(13) 0.0395(17) 0.0025(11) -0.0051(12) -0.0011(10) C14 0.0176(13) 0.0156(11) 0.0253(14) 0.0019(10) -0.0038(10) 0.0027(10) C15 0.0149(12) 0.0161(12) 0.0311(15) 0.0027(10) -0.0060(10) 0.0035(10) C16 0.0210(14) 0.0218(13) 0.0324(16) -0.0017(11) -0.0116(12) 0.0039(11) C17 0.0270(15) 0.0249(14) 0.0267(15) -0.0023(11) -0.0054(12) 0.0059(12) C18 0.0240(14) 0.0239(13) 0.0270(14) 0.0044(11) 0.0009(11) 0.0052(11) C19 0.0188(13) 0.0184(12) 0.0289(15) 0.0026(10) -0.0017(11) 0.0006(10) C20 0.0163(13) 0.0165(12) 0.0364(16) 0.0065(11) -0.0064(11) 0.0006(10) O5 0.179(5) 0.113(4) 0.101(4) 0.035(3) 0.060(4) 0.044(4) _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 C9 1.794(3) . ? S1 S2 2.0546(9) . ? S2 C14 1.794(3) . ? O1 C7 1.285(3) . ? O2 C7 1.232(3) . ? O3 C20 1.323(3) . ? O3 H3O 0.8400(11) . ? O4 C20 1.216(4) . ? N1 C1 1.338(4) . ? N1 C5 1.340(4) . ? N1 H1N 0.8801(10) . ? C1 C2 1.371(4) . ? C1 H1 0.9500 . ? C2 C3 1.389(4) . ? C2 H2 0.9500 . ? C3 C4 1.390(4) . ? C3 C6 1.510(4) . ? C4 C5 1.380(4) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C6 1.521(5) 2_365 ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.503(4) . ? C8 C13 1.395(4) . ? C8 C9 1.407(4) . ? C9 C10 1.392(4) . ? C10 C11 1.386(4) . ? C10 H10 0.9500 . ? C11 C12 1.386(4) . ? C11 H11 0.9500 . ? C12 C13 1.385(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C19 1.398(4) . ? C14 C15 1.410(4) . ? C15 C16 1.397(4) . ? C15 C20 1.481(4) . ? C16 C17 1.386(4) . ? C16 H16 0.9500 . ? C17 C18 1.380(4) . ? C17 H17 0.9500 . ? C18 C19 1.387(4) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? O5 C21 1.291(8) . ? O5 C21 1.291(8) . ? O5 H5O 0.8401(10) . ? C21 C22 1.430(13) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C21 C24 1.61(2) . ? C21 H21C 0.9900 . ? C21 H21D 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? 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 S1 S2 105.79(9) . . ? C14 S2 S1 105.20(9) . . ? C20 O3 H3O 100(3) . . ? C1 N1 C5 121.3(3) . . ? C1 N1 H1N 123(3) . . ? C5 N1 H1N 115(3) . . ? N1 C1 C2 120.5(3) . . ? N1 C1 H1 119.8 . . ? C2 C1 H1 119.8 . . ? C1 C2 C3 120.2(3) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C2 C3 C4 118.0(3) . . ? C2 C3 C6 118.9(3) . . ? C4 C3 C6 123.1(3) . . ? C5 C4 C3 119.8(3) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? N1 C5 C4 120.3(3) . . ? N1 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C3 C6 C6 115.1(3) . 2_365 ? C3 C6 H6A 108.5 . . ? C6 C6 H6A 108.5 2_365 . ? C3 C6 H6B 108.5 . . ? C6 C6 H6B 108.5 2_365 . ? H6A C6 H6B 107.5 . . ? O2 C7 O1 123.6(2) . . ? O2 C7 C8 119.9(2) . . ? O1 C7 C8 116.5(2) . . ? C13 C8 C9 118.9(2) . . ? C13 C8 C7 119.2(2) . . ? C9 C8 C7 121.9(2) . . ? C10 C9 C8 119.3(2) . . ? C10 C9 S1 121.0(2) . . ? C8 C9 S1 119.7(2) . . ? C9 C10 C11 120.7(2) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C12 C11 C10 120.5(3) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C13 C12 C11 119.0(3) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C8 121.6(3) . . ? C12 C13 H13 119.2 . . ? C8 C13 H13 119.2 . . ? C19 C14 C15 118.9(3) . . ? C19 C14 S2 120.6(2) . . ? C15 C14 S2 120.4(2) . . ? C16 C15 C14 119.2(3) . . ? C16 C15 C20 119.6(2) . . ? C14 C15 C20 121.1(3) . . ? C17 C16 C15 121.4(3) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C18 C17 C16 118.9(3) . . ? C18 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? C17 C18 C19 121.3(3) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C14 C19 C18 120.3(3) . . ? C14 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? O4 C20 O3 123.5(3) . . ? O4 C20 C15 122.8(2) . . ? O3 C20 C15 113.7(3) . . ? C21 O5 C21 0.0(6) . . ? C21 O5 H5O 91(7) . . ? C21 O5 H5O 91(7) . . ? O5 C21 C22 116.8(7) . . ? O5 C21 H21A 108.1 . . ? C22 C21 H21A 108.1 . . ? O5 C21 H21B 108.1 . . ? C22 C21 H21B 108.1 . . ? H21A C21 H21B 107.3 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O5 C21 C24 89.9(10) . . ? O5 C21 H21C 113.7 . . ? C24 C21 H21C 113.7 . . ? O5 C21 H21D 113.7 . . ? C24 C21 H21D 113.7 . . ? H21C C21 H21D 110.9 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 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 C9 S1 S2 C14 -80.70(13) . . . . ? C5 N1 C1 C2 -0.5(5) . . . . ? N1 C1 C2 C3 1.0(5) . . . . ? C1 C2 C3 C4 -0.9(4) . . . . ? C1 C2 C3 C6 177.8(3) . . . . ? C2 C3 C4 C5 0.4(5) . . . . ? C6 C3 C4 C5 -178.3(3) . . . . ? C1 N1 C5 C4 -0.1(5) . . . . ? C3 C4 C5 N1 0.2(5) . . . . ? C2 C3 C6 C6 175.2(3) . . . 2_365 ? C4 C3 C6 C6 -6.1(5) . . . 2_365 ? O2 C7 C8 C13 -167.8(3) . . . . ? O1 C7 C8 C13 11.2(4) . . . . ? O2 C7 C8 C9 11.8(4) . . . . ? O1 C7 C8 C9 -169.3(3) . . . . ? C13 C8 C9 C10 -0.9(4) . . . . ? C7 C8 C9 C10 179.6(2) . . . . ? C13 C8 C9 S1 -178.5(2) . . . . ? C7 C8 C9 S1 2.0(4) . . . . ? S2 S1 C9 C10 3.8(2) . . . . ? S2 S1 C9 C8 -178.65(19) . . . . ? C8 C9 C10 C11 1.0(4) . . . . ? S1 C9 C10 C11 178.5(2) . . . . ? C9 C10 C11 C12 -0.5(5) . . . . ? C10 C11 C12 C13 -0.1(5) . . . . ? C11 C12 C13 C8 0.1(5) . . . . ? C9 C8 C13 C12 0.4(4) . . . . ? C7 C8 C13 C12 179.9(3) . . . . ? S1 S2 C14 C19 18.0(2) . . . . ? S1 S2 C14 C15 -161.64(19) . . . . ? C19 C14 C15 C16 -1.9(4) . . . . ? S2 C14 C15 C16 177.82(19) . . . . ? C19 C14 C15 C20 -179.8(2) . . . . ? S2 C14 C15 C20 -0.1(3) . . . . ? C14 C15 C16 C17 1.7(4) . . . . ? C20 C15 C16 C17 179.6(2) . . . . ? C15 C16 C17 C18 -0.7(4) . . . . ? C16 C17 C18 C19 -0.1(4) . . . . ? C15 C14 C19 C18 1.1(4) . . . . ? S2 C14 C19 C18 -178.6(2) . . . . ? C17 C18 C19 C14 -0.1(4) . . . . ? C16 C15 C20 O4 175.4(2) . . . . ? C14 C15 C20 O4 -6.7(4) . . . . ? C16 C15 C20 O3 -5.5(3) . . . . ? C14 C15 C20 O3 172.4(2) . . . . ? C21 O5 C21 C22 0(100) . . . . ? C21 O5 C21 C24 0(100) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.90 _refine_diff_density_min -0.75 _refine_diff_density_rms 0.103