# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2007 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Jesus Sanmartin' 'Manuel Bermejo' 'Matilde Fondo' 'Ana M. Garcia Deibe' 'Fernando Novio' _publ_contact_author_name 'Jesus Sanmartin' _publ_contact_author_address ; University of Santiago de Compostela Santiago de Compostela E-15782 SPAIN ; _publ_contact_author_email QISUSO@USC.ES _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Trimorphism of an asymmetric disulfonamide Schiff base ; data_A _database_code_depnum_ccdc_archive 'CCDC 646377' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H16 N2 O2 S' _chemical_formula_sum 'C14 H16 N2 O2 S' _chemical_formula_weight 276.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.184(3) _cell_length_b 5.7697(10) _cell_length_c 18.696(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.833(16) _cell_angle_gamma 90.00 _cell_volume 1396.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 18.83 _cell_measurement_theta_max 41.94 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 2.060 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.2914 _exptl_absorpt_correction_T_max 0.6377 _exptl_absorpt_process_details ? _exptl_special_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 7 Theta correction was applied. Weighted transmission curves were used. No Fourier smoothing was applied. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CAD4 Enraf Nonius' _diffrn_measurement_method omega/2-theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 187 _diffrn_standards_interval_time 86 _diffrn_standards_decay_% 6 _diffrn_reflns_number 2872 _diffrn_reflns_av_R_equivalents 0.0680 _diffrn_reflns_av_sigmaI/netI 0.0421 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 3.79 _diffrn_reflns_theta_max 73.08 _reflns_number_total 2785 _reflns_number_gt 1431 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4-Express Software (Nonius, 1994)' _computing_cell_refinement 'CAD4-Express Software (Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3-for windows (Farrugia, 1997)' _computing_publication_material 'WINGX (Farrugia, 1999)' _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^)+(0.1166P)^2^+0.0067P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2785 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1395 _refine_ls_R_factor_gt 0.0632 _refine_ls_wR_factor_ref 0.2117 _refine_ls_wR_factor_gt 0.1731 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1676(3) 0.9128(7) 0.3727(2) 0.0808(10) Uani 1 1 d . . . C2 C 0.1576(4) 0.9988(10) 0.4391(3) 0.1252(18) Uani 1 1 d . . . H2 H 0.2003 0.9465 0.4814 0.150 Uiso 1 1 calc R . . C3 C 0.0831(4) 1.1644(12) 0.4426(3) 0.143(2) Uani 1 1 d . . . H3 H 0.0760 1.2225 0.4878 0.172 Uiso 1 1 calc R . . C4 C 0.0183(3) 1.2468(9) 0.3804(3) 0.1042(14) Uani 1 1 d . . . C40 C -0.0600(4) 1.4389(11) 0.3850(3) 0.141(2) Uani 1 1 d . . . H40A H -0.0245 1.5840 0.3948 0.212 Uiso 1 1 calc R . . H40B H -0.0967 1.4045 0.4234 0.212 Uiso 1 1 calc R . . H40C H -0.1080 1.4488 0.3396 0.212 Uiso 1 1 calc R . . C5 C 0.0296(3) 1.1567(8) 0.3157(3) 0.1014(13) Uani 1 1 d . . . H5 H -0.0135 1.2067 0.2732 0.122 Uiso 1 1 calc R . . C6 C 0.1036(3) 0.9928(8) 0.3115(2) 0.0947(12) Uani 1 1 d . . . H6 H 0.1103 0.9349 0.2662 0.114 Uiso 1 1 calc R . . S1 S 0.26401(7) 0.71149(18) 0.36578(5) 0.0866(4) Uani 1 1 d . . . O2 O 0.3058(2) 0.6304(5) 0.43722(15) 0.1094(10) Uani 1 1 d . . . O1 O 0.2231(2) 0.5511(5) 0.30951(16) 0.1025(9) Uani 1 1 d . . . N1 N 0.3569(2) 0.8444(6) 0.33703(19) 0.0844(9) Uani 1 1 d . . . C7 C 0.4203(3) 1.0197(6) 0.3823(2) 0.0918(12) Uani 1 1 d . . . H7A H 0.4167 0.9956 0.4331 0.110 Uiso 1 1 calc R . . H7B H 0.3938 1.1734 0.3684 0.110 Uiso 1 1 calc R . . C8 C 0.5300(3) 1.0021(6) 0.3725(2) 0.0827(11) Uani 1 1 d . . . C9 C 0.5741(4) 1.1636(9) 0.3333(3) 0.1238(18) Uani 1 1 d . . . H9 H 0.5349 1.2898 0.3132 0.149 Uiso 1 1 calc R . . C10 C 0.6752(4) 1.1432(12) 0.3228(3) 0.139(2) Uani 1 1 d . . . H10 H 0.7035 1.2551 0.2966 0.167 Uiso 1 1 calc R . . C11 C 0.7324(4) 0.9578(12) 0.3513(3) 0.1216(17) Uani 1 1 d . . . H11 H 0.7999 0.9416 0.3440 0.146 Uiso 1 1 calc R . . C12 C 0.6914(3) 0.7957(9) 0.3905(3) 0.1078(14) Uani 1 1 d . . . H12 H 0.7315 0.6696 0.4096 0.129 Uiso 1 1 calc R . . C13 C 0.5909(3) 0.8151(7) 0.4025(2) 0.0838(10) Uani 1 1 d . . . N2 N 0.5526(4) 0.6568(9) 0.4448(3) 0.1207(16) Uani 1 1 d . . . H1A H 0.337(3) 0.894(7) 0.287(2) 0.101(13) Uiso 1 1 d . . . H2B H 0.491(4) 0.633(8) 0.437(3) 0.112(18) Uiso 1 1 d . . . H2A H 0.592(4) 0.556(10) 0.467(3) 0.15(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.079(2) 0.084(2) 0.079(2) -0.005(2) 0.0146(17) -0.0066(18) C2 0.126(4) 0.158(5) 0.086(3) -0.015(3) 0.008(3) 0.039(4) C3 0.130(4) 0.199(6) 0.098(3) -0.039(4) 0.013(3) 0.043(4) C4 0.081(2) 0.110(3) 0.121(4) -0.022(3) 0.018(2) -0.006(2) C40 0.107(3) 0.148(5) 0.169(5) -0.037(4) 0.024(3) 0.022(3) C5 0.084(2) 0.115(3) 0.101(3) -0.003(3) 0.006(2) -0.004(2) C6 0.086(2) 0.108(3) 0.087(3) -0.003(2) 0.0101(19) 0.008(2) S1 0.0908(7) 0.0841(6) 0.0827(6) 0.0017(6) 0.0105(4) -0.0003(5) O2 0.121(2) 0.114(2) 0.0898(19) 0.0212(18) 0.0120(15) 0.0155(18) O1 0.1078(19) 0.0924(17) 0.106(2) -0.0176(17) 0.0173(15) -0.0186(15) N1 0.0737(18) 0.092(2) 0.085(2) 0.0051(18) 0.0089(15) -0.0027(15) C7 0.083(2) 0.072(2) 0.114(3) -0.005(2) 0.002(2) 0.0063(18) C8 0.082(2) 0.076(2) 0.083(2) 0.000(2) -0.0020(17) -0.0013(17) C9 0.106(3) 0.111(3) 0.140(4) 0.036(3) -0.014(3) -0.021(3) C10 0.106(4) 0.161(5) 0.142(5) 0.043(4) 0.000(3) -0.043(4) C11 0.090(3) 0.160(5) 0.117(4) -0.003(4) 0.025(3) -0.017(3) C12 0.087(3) 0.110(3) 0.123(4) 0.003(3) 0.014(2) 0.016(3) C13 0.084(2) 0.085(2) 0.082(2) 0.004(2) 0.0125(17) 0.010(2) N2 0.102(3) 0.125(4) 0.135(4) 0.053(3) 0.023(3) 0.023(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.368(6) . ? C1 C6 1.368(5) . ? C1 S1 1.744(4) . ? C2 C3 1.380(7) . ? C2 H2 0.9300 . ? C3 C4 1.391(6) . ? C3 H3 0.9300 . ? C4 C5 1.351(6) . ? C4 C40 1.528(6) . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? C5 C6 1.371(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? S1 O2 1.425(3) . ? S1 O1 1.428(3) . ? S1 N1 1.620(4) . ? N1 C7 1.474(4) . ? N1 H1A 0.96(4) . ? C7 C8 1.495(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.380(6) . ? C8 C13 1.398(5) . ? C9 C10 1.389(7) . ? C9 H9 0.9300 . ? C10 C11 1.358(7) . ? C10 H10 0.9300 . ? C11 C12 1.361(7) . ? C11 H11 0.9300 . ? C12 C13 1.390(6) . ? C12 H12 0.9300 . ? C13 N2 1.365(6) . ? N2 H2B 0.81(5) . ? N2 H2A 0.84(6) . ? 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 C2 C1 C6 119.2(4) . . ? C2 C1 S1 120.3(3) . . ? C6 C1 S1 120.5(3) . . ? C1 C2 C3 119.0(4) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 121.9(5) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? C5 C4 C3 117.6(5) . . ? C5 C4 C40 121.3(5) . . ? C3 C4 C40 121.1(5) . . ? C4 C40 H40A 109.5 . . ? C4 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C4 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C4 C5 C6 121.0(4) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C1 C6 C5 121.3(4) . . ? C1 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? O2 S1 O1 120.25(19) . . ? O2 S1 N1 106.46(17) . . ? O1 S1 N1 105.48(18) . . ? O2 S1 C1 107.94(19) . . ? O1 S1 C1 107.81(17) . . ? N1 S1 C1 108.44(18) . . ? C7 N1 S1 121.1(3) . . ? C7 N1 H1A 112(2) . . ? S1 N1 H1A 112(2) . . ? N1 C7 C8 109.9(3) . . ? N1 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? N1 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? C9 C8 C13 117.8(4) . . ? C9 C8 C7 122.2(4) . . ? C13 C8 C7 120.0(4) . . ? C8 C9 C10 121.9(5) . . ? C8 C9 H9 119.0 . . ? C10 C9 H9 119.0 . . ? C11 C10 C9 119.2(5) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C10 C11 C12 120.4(5) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C13 121.2(5) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? N2 C13 C12 120.5(4) . . ? N2 C13 C8 120.1(4) . . ? C12 C13 C8 119.4(4) . . ? C13 N2 H2B 119(3) . . ? C13 N2 H2A 119(4) . . ? H2B N2 H2A 119(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 C6 C1 C2 C3 -0.1(8) . . . . ? S1 C1 C2 C3 177.6(4) . . . . ? C1 C2 C3 C4 -0.3(9) . . . . ? C2 C3 C4 C5 0.8(9) . . . . ? C2 C3 C4 C40 -176.9(5) . . . . ? C3 C4 C5 C6 -1.1(7) . . . . ? C40 C4 C5 C6 176.6(4) . . . . ? C2 C1 C6 C5 -0.2(7) . . . . ? S1 C1 C6 C5 -177.8(3) . . . . ? C4 C5 C6 C1 0.8(7) . . . . ? C2 C1 S1 O2 12.4(4) . . . . ? C6 C1 S1 O2 -170.0(3) . . . . ? C2 C1 S1 O1 143.7(4) . . . . ? C6 C1 S1 O1 -38.7(4) . . . . ? C2 C1 S1 N1 -102.6(4) . . . . ? C6 C1 S1 N1 75.0(4) . . . . ? O2 S1 N1 C7 -49.2(3) . . . . ? O1 S1 N1 C7 -178.0(3) . . . . ? C1 S1 N1 C7 66.7(3) . . . . ? S1 N1 C7 C8 142.9(3) . . . . ? N1 C7 C8 C9 106.6(5) . . . . ? N1 C7 C8 C13 -72.2(5) . . . . ? C13 C8 C9 C10 0.5(7) . . . . ? C7 C8 C9 C10 -178.3(4) . . . . ? C8 C9 C10 C11 0.7(8) . . . . ? C9 C10 C11 C12 -0.9(9) . . . . ? C10 C11 C12 C13 -0.1(8) . . . . ? C11 C12 C13 N2 -176.9(5) . . . . ? C11 C12 C13 C8 1.3(7) . . . . ? C9 C8 C13 N2 176.8(4) . . . . ? C7 C8 C13 N2 -4.4(6) . . . . ? C9 C8 C13 C12 -1.4(6) . . . . ? C7 C8 C13 C12 177.4(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O1 0.96(4) 2.05(4) 2.993(4) 168(3) 2 N2 H2B O2 0.81(5) 2.44(5) 3.235(6) 166(5) . N2 H2A O2 0.84(6) 2.30(6) 3.091(5) 158(6) 3_666 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 73.08 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.218 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.051 # Attachment 'M.cif' data_M _database_code_depnum_ccdc_archive 'CCDC 646378' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H27 N3 O4 S2' _chemical_formula_sum 'C28 H27 N3 O4 S2' _chemical_formula_weight 533.65 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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.0457(15) _cell_length_b 18.882(3) _cell_length_c 16.057(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.144(3) _cell_angle_gamma 90.00 _cell_volume 2647.4(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1732 _cell_measurement_theta_min 2.359 _cell_measurement_theta_max 23.519 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.240 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.7903 _exptl_absorpt_correction_T_max 0.9370 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart CCD-1000' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24691 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0422 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 26.37 _reflns_number_total 5404 _reflns_number_gt 3227 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER Smart' _computing_cell_refinement 'BRUKER Smart' _computing_data_reduction ? _computing_structure_solution 'SIR-92 (Altomare, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material ? _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^)+(0.0687P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5404 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0832 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1286 _refine_ls_wR_factor_gt 0.1168 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1894(2) 0.07216(12) -0.09182(13) 0.0418(5) Uani 1 1 d . . . C2 C 0.0577(3) 0.11129(16) -0.11313(17) 0.0733(8) Uani 1 1 d . . . H2 H 0.0050 0.1212 -0.0719 0.088 Uiso 1 1 calc R . . C3 C 0.0036(4) 0.13604(17) -0.19672(19) 0.0846(10) Uani 1 1 d . . . H3 H -0.0849 0.1634 -0.2107 0.102 Uiso 1 1 calc R . . C4 C 0.0770(3) 0.12130(13) -0.25976(16) 0.0606(7) Uani 1 1 d . . . C40 C 0.0164(4) 0.14818(19) -0.35092(19) 0.1008(11) Uani 1 1 d . . . H40A H -0.0744 0.1758 -0.3548 0.151 Uiso 0.57(4) 1 calc PR . . H40B H -0.0077 0.1087 -0.3898 0.151 Uiso 0.57(4) 1 calc PR . . H40C H 0.0927 0.1771 -0.3660 0.151 Uiso 0.57(4) 1 calc PR . . H40D H 0.0814 0.1320 -0.3856 0.151 Uiso 0.43(4) 1 calc PR . . H40E H 0.0148 0.1990 -0.3506 0.151 Uiso 0.43(4) 1 calc PR . . H40F H -0.0856 0.1306 -0.3744 0.151 Uiso 0.43(4) 1 calc PR . . C5 C 0.2063(3) 0.08028(15) -0.23681(16) 0.0660(7) Uani 1 1 d . . . H5 H 0.2569 0.0686 -0.2784 0.079 Uiso 1 1 calc R . . C6 C 0.2629(3) 0.05593(14) -0.15418(15) 0.0575(7) Uani 1 1 d . . . H6 H 0.3512 0.0284 -0.1403 0.069 Uiso 1 1 calc R . . S1 S 0.26882(6) 0.04502(3) 0.01506(4) 0.04383(18) Uani 1 1 d . . . O1 O 0.31476(18) -0.02773(8) 0.01524(10) 0.0538(4) Uani 1 1 d . . . O2 O 0.16693(19) 0.06563(9) 0.06488(10) 0.0605(5) Uani 1 1 d . . . N1 N 0.4263(2) 0.08853(10) 0.05085(13) 0.0463(5) Uani 1 1 d . . . C7 C 0.4240(3) 0.16706(12) 0.05158(15) 0.0493(6) Uani 1 1 d . . . H7A H 0.4459 0.1839 0.1106 0.059 Uiso 1 1 calc R . . H7B H 0.3230 0.1838 0.0211 0.059 Uiso 1 1 calc R . . C8 C 0.5412(3) 0.19596(11) 0.00918(14) 0.0469(6) Uani 1 1 d . . . C9 C 0.4958(4) 0.22569(14) -0.07249(17) 0.0697(8) Uani 1 1 d . . . H9 H 0.3921 0.2291 -0.1003 0.084 Uiso 1 1 calc R . . C10 C 0.6021(5) 0.25006(16) -0.1127(2) 0.0862(10) Uani 1 1 d . . . H10 H 0.5698 0.2707 -0.1670 0.103 Uiso 1 1 calc R . . C11 C 0.7551(4) 0.24433(15) -0.0738(2) 0.0797(9) Uani 1 1 d . . . H11 H 0.8266 0.2603 -0.1019 0.096 Uiso 1 1 calc R . . C12 C 0.8032(3) 0.21469(13) 0.00741(17) 0.0621(7) Uani 1 1 d . . . H12 H 0.9074 0.2112 0.0341 0.075 Uiso 1 1 calc R . . C13 C 0.6974(3) 0.19004(11) 0.04951(14) 0.0441(5) Uani 1 1 d . . . N2 N 0.7412(2) 0.16270(10) 0.13418(11) 0.0454(5) Uani 1 1 d . . . C14 C 0.8641(3) 0.12643(12) 0.16011(14) 0.0457(6) Uani 1 1 d . . . H14 H 0.9188 0.1154 0.1202 0.055 Uiso 1 1 calc R . . C15 C 0.9232(2) 0.10156(12) 0.24790(14) 0.0442(5) Uani 1 1 d . . . C16 C 1.0639(3) 0.06658(14) 0.26877(17) 0.0583(7) Uani 1 1 d . . . H16 H 1.1142 0.0588 0.2259 0.070 Uiso 1 1 calc R . . C17 C 1.1299(3) 0.04331(16) 0.35119(18) 0.0666(7) Uani 1 1 d . . . H17 H 1.2237 0.0200 0.3638 0.080 Uiso 1 1 calc R . . C18 C 1.0568(3) 0.05473(15) 0.41440(17) 0.0635(7) Uani 1 1 d . . . H18 H 1.1017 0.0392 0.4703 0.076 Uiso 1 1 calc R . . C19 C 0.9174(3) 0.08898(14) 0.39658(15) 0.0592(7) Uani 1 1 d . . . H19 H 0.8692 0.0963 0.4404 0.071 Uiso 1 1 calc R . . C20 C 0.8491(2) 0.11245(12) 0.31430(14) 0.0464(6) Uani 1 1 d . . . N3 N 0.7081(2) 0.14843(12) 0.29315(14) 0.0565(6) Uani 1 1 d . . . S2 S 0.57115(8) 0.13941(4) 0.34070(4) 0.0610(2) Uani 1 1 d . . . O3 O 0.6250(2) 0.15946(11) 0.42870(11) 0.0774(6) Uani 1 1 d . . . O4 O 0.4438(2) 0.17564(10) 0.28561(11) 0.0736(6) Uani 1 1 d . . . C21 C 0.5303(3) 0.04856(15) 0.33785(15) 0.0546(6) Uani 1 1 d . . . C22 C 0.5788(3) 0.00652(18) 0.41162(16) 0.0633(7) Uani 1 1 d . . . H22 H 0.6343 0.0266 0.4632 0.076 Uiso 1 1 calc R . . C23 C 0.5449(3) -0.06386(18) 0.40806(18) 0.0696(8) Uani 1 1 d . . . H23 H 0.5778 -0.0912 0.4576 0.084 Uiso 1 1 calc R . . C24 C 0.4627(3) -0.09577(16) 0.33252(18) 0.0679(8) Uani 1 1 d . . . C240 C 0.4287(5) -0.17331(19) 0.3303(2) 0.1058(12) Uani 1 1 d . . . H24A H 0.5186 -0.1994 0.3280 0.159 Uiso 1 1 calc R . . H24B H 0.3471 -0.1840 0.2803 0.159 Uiso 1 1 calc R . . H24C H 0.3987 -0.1863 0.3813 0.159 Uiso 1 1 calc R . . C25 C 0.4156(3) -0.05347(17) 0.25908(17) 0.0676(8) Uani 1 1 d . . . H25 H 0.3602 -0.0737 0.2075 0.081 Uiso 1 1 calc R . . C26 C 0.4497(3) 0.01719(16) 0.26173(16) 0.0593(7) Uani 1 1 d . . . H26 H 0.4183 0.0444 0.2119 0.071 Uiso 1 1 calc R . . H1A H 0.491(3) 0.0727(12) 0.0308(15) 0.046(7) Uiso 1 1 d . . . H3A H 0.676(3) 0.1596(13) 0.2404(16) 0.056(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0372(12) 0.0485(13) 0.0398(13) -0.0023(10) 0.0100(10) -0.0006(10) C2 0.0651(18) 0.103(2) 0.0515(17) -0.0035(15) 0.0138(14) 0.0338(17) C3 0.076(2) 0.104(2) 0.062(2) 0.0029(17) -0.0015(17) 0.0460(18) C4 0.0706(18) 0.0577(16) 0.0477(15) 0.0091(12) 0.0049(14) 0.0004(14) C40 0.126(3) 0.101(3) 0.064(2) 0.0284(18) 0.005(2) 0.016(2) C5 0.0683(18) 0.089(2) 0.0463(16) 0.0097(14) 0.0253(13) 0.0096(16) C6 0.0526(15) 0.0789(18) 0.0443(14) 0.0083(13) 0.0181(12) 0.0190(13) S1 0.0417(3) 0.0521(4) 0.0397(3) 0.0017(3) 0.0143(2) 0.0011(3) O1 0.0589(10) 0.0453(10) 0.0570(10) 0.0060(8) 0.0147(8) 0.0014(8) O2 0.0552(10) 0.0843(12) 0.0487(10) -0.0021(9) 0.0257(8) 0.0021(9) N1 0.0417(12) 0.0465(12) 0.0496(12) 0.0021(9) 0.0098(10) 0.0049(9) C7 0.0474(14) 0.0466(14) 0.0520(14) -0.0044(11) 0.0096(11) 0.0064(11) C8 0.0636(16) 0.0335(12) 0.0445(14) 0.0001(10) 0.0159(12) 0.0041(11) C9 0.091(2) 0.0566(16) 0.0617(18) 0.0127(14) 0.0198(16) 0.0189(15) C10 0.135(3) 0.069(2) 0.067(2) 0.0319(16) 0.049(2) 0.030(2) C11 0.122(3) 0.0562(18) 0.083(2) 0.0128(16) 0.066(2) 0.0026(18) C12 0.0750(18) 0.0587(16) 0.0633(17) -0.0029(13) 0.0369(15) -0.0097(14) C13 0.0561(15) 0.0381(13) 0.0435(13) -0.0074(10) 0.0223(12) -0.0053(11) N2 0.0466(12) 0.0512(11) 0.0411(11) -0.0063(9) 0.0163(9) -0.0073(9) C14 0.0414(14) 0.0570(14) 0.0446(14) -0.0139(11) 0.0220(11) -0.0091(11) C15 0.0346(12) 0.0583(14) 0.0418(13) -0.0074(11) 0.0137(10) -0.0055(11) C16 0.0426(14) 0.0770(18) 0.0608(17) -0.0049(14) 0.0231(13) 0.0008(13) C17 0.0391(14) 0.092(2) 0.0706(19) 0.0072(15) 0.0174(13) 0.0108(13) C18 0.0443(15) 0.088(2) 0.0558(16) 0.0112(14) 0.0086(13) -0.0002(14) C19 0.0506(16) 0.0860(19) 0.0445(15) 0.0037(13) 0.0186(12) -0.0010(14) C20 0.0361(13) 0.0609(15) 0.0442(14) -0.0034(11) 0.0144(10) -0.0001(11) N3 0.0510(13) 0.0819(15) 0.0413(13) 0.0081(11) 0.0205(10) 0.0148(11) S2 0.0520(4) 0.0908(5) 0.0482(4) 0.0005(3) 0.0272(3) 0.0166(4) O3 0.0795(13) 0.1116(16) 0.0500(11) -0.0112(10) 0.0329(10) 0.0122(11) O4 0.0595(11) 0.0962(14) 0.0726(12) 0.0116(10) 0.0303(10) 0.0327(10) C21 0.0360(13) 0.0906(19) 0.0429(14) 0.0038(13) 0.0205(11) 0.0114(12) C22 0.0480(15) 0.106(2) 0.0385(15) 0.0092(15) 0.0153(12) 0.0107(15) C23 0.0604(17) 0.100(2) 0.0493(17) 0.0235(16) 0.0166(14) 0.0200(17) C24 0.0594(17) 0.087(2) 0.0596(18) 0.0090(16) 0.0187(14) 0.0170(15) C240 0.113(3) 0.105(3) 0.090(3) 0.008(2) 0.009(2) 0.012(2) C25 0.0571(17) 0.099(2) 0.0444(16) 0.0001(15) 0.0092(13) 0.0106(16) C26 0.0489(15) 0.092(2) 0.0386(15) 0.0119(14) 0.0137(12) 0.0190(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.367(3) . ? C1 C6 1.374(3) . ? C1 S1 1.755(2) . ? C2 C3 1.384(4) . ? C2 H2 0.9300 . ? C3 C4 1.376(4) . ? C3 H3 0.9300 . ? C4 C5 1.371(4) . ? C4 C40 1.510(4) . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? C40 H40D 0.9600 . ? C40 H40E 0.9600 . ? C40 H40F 0.9600 . ? C5 C6 1.371(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? S1 O2 1.4235(16) . ? S1 O1 1.4348(16) . ? S1 N1 1.615(2) . ? N1 C7 1.483(3) . ? N1 H1A 0.80(2) . ? C7 C8 1.504(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.386(3) . ? C8 C13 1.397(3) . ? C9 C10 1.370(4) . ? C9 H9 0.9300 . ? C10 C11 1.366(4) . ? C10 H10 0.9300 . ? C11 C12 1.380(4) . ? C11 H11 0.9300 . ? C12 C13 1.389(3) . ? C12 H12 0.9300 . ? C13 N2 1.411(3) . ? N2 C14 1.279(3) . ? C14 C15 1.449(3) . ? C14 H14 0.9300 . ? C15 C16 1.394(3) . ? C15 C20 1.415(3) . ? C16 C17 1.374(3) . ? C16 H16 0.9300 . ? C17 C18 1.366(3) . ? C17 H17 0.9300 . ? C18 C19 1.379(3) . ? C18 H18 0.9300 . ? C19 C20 1.377(3) . ? C19 H19 0.9300 . ? C20 N3 1.406(3) . ? N3 S2 1.625(2) . ? N3 H3A 0.85(2) . ? S2 O3 1.4205(18) . ? S2 O4 1.4302(18) . ? S2 C21 1.753(3) . ? C21 C26 1.382(3) . ? C21 C22 1.398(3) . ? C22 C23 1.362(4) . ? C22 H22 0.9300 . ? C23 C24 1.384(4) . ? C23 H23 0.9300 . ? C24 C25 1.396(4) . ? C24 C240 1.495(4) . ? C240 H24A 0.9600 . ? C240 H24B 0.9600 . ? C240 H24C 0.9600 . ? C25 C26 1.368(4) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? 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 C2 C1 C6 119.6(2) . . ? C2 C1 S1 120.67(18) . . ? C6 C1 S1 119.67(17) . . ? C1 C2 C3 119.3(3) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C4 C3 C2 121.9(3) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C5 C4 C3 117.3(2) . . ? C5 C4 C40 121.2(3) . . ? C3 C4 C40 121.5(3) . . ? C4 C40 H40A 109.5 . . ? C4 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C4 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C4 C40 H40D 109.5 . . ? H40A C40 H40D 141.1 . . ? H40B C40 H40D 56.3 . . ? H40C C40 H40D 56.3 . . ? C4 C40 H40E 109.5 . . ? H40A C40 H40E 56.3 . . ? H40B C40 H40E 141.1 . . ? H40C C40 H40E 56.3 . . ? H40D C40 H40E 109.5 . . ? C4 C40 H40F 109.5 . . ? H40A C40 H40F 56.3 . . ? H40B C40 H40F 56.3 . . ? H40C C40 H40F 141.1 . . ? H40D C40 H40F 109.5 . . ? H40E C40 H40F 109.5 . . ? C4 C5 C6 121.8(2) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C5 C6 C1 120.1(2) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? O2 S1 O1 119.36(10) . . ? O2 S1 N1 107.54(11) . . ? O1 S1 N1 104.97(10) . . ? O2 S1 C1 108.05(10) . . ? O1 S1 C1 109.02(10) . . ? N1 S1 C1 107.30(10) . . ? C7 N1 S1 119.93(16) . . ? C7 N1 H1A 113.0(17) . . ? S1 N1 H1A 109.8(17) . . ? N1 C7 C8 110.27(18) . . ? N1 C7 H7A 109.6 . . ? C8 C7 H7A 109.6 . . ? N1 C7 H7B 109.6 . . ? C8 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? C9 C8 C13 119.0(2) . . ? C9 C8 C7 120.4(2) . . ? C13 C8 C7 120.5(2) . . ? C10 C9 C8 120.7(3) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C11 C10 C9 120.7(3) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 119.7(3) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C12 C13 120.6(3) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C8 119.3(2) . . ? C12 C13 N2 122.4(2) . . ? C8 C13 N2 118.1(2) . . ? C14 N2 C13 120.73(19) . . ? N2 C14 C15 124.0(2) . . ? N2 C14 H14 118.0 . . ? C15 C14 H14 118.0 . . ? C16 C15 C20 118.0(2) . . ? C16 C15 C14 118.0(2) . . ? C20 C15 C14 124.0(2) . . ? C17 C16 C15 121.5(2) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C18 C17 C16 119.5(2) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C17 C18 C19 120.9(2) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C20 C19 C18 120.4(2) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C19 C20 N3 122.6(2) . . ? C19 C20 C15 119.6(2) . . ? N3 C20 C15 117.8(2) . . ? C20 N3 S2 126.19(18) . . ? C20 N3 H3A 114.5(16) . . ? S2 N3 H3A 113.0(16) . . ? O3 S2 O4 119.96(12) . . ? O3 S2 N3 109.50(12) . . ? O4 S2 N3 104.42(11) . . ? O3 S2 C21 107.58(12) . . ? O4 S2 C21 108.77(12) . . ? N3 S2 C21 105.76(11) . . ? C26 C21 C22 118.8(3) . . ? C26 C21 S2 120.1(2) . . ? C22 C21 S2 121.1(2) . . ? C23 C22 C21 120.1(3) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C23 C24 121.7(3) . . ? C22 C23 H23 119.2 . . ? C24 C23 H23 119.2 . . ? C23 C24 C25 117.8(3) . . ? C23 C24 C240 120.5(3) . . ? C25 C24 C240 121.7(3) . . ? C24 C240 H24A 109.5 . . ? C24 C240 H24B 109.5 . . ? H24A C240 H24B 109.5 . . ? C24 C240 H24C 109.5 . . ? H24A C240 H24C 109.5 . . ? H24B C240 H24C 109.5 . . ? C26 C25 C24 121.0(3) . . ? C26 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? C25 C26 C21 120.5(2) . . ? C25 C26 H26 119.7 . . ? C21 C26 H26 119.7 . . ? 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 C6 C1 C2 C3 -2.3(4) . . . . ? S1 C1 C2 C3 175.6(2) . . . . ? C1 C2 C3 C4 1.3(5) . . . . ? C2 C3 C4 C5 0.5(5) . . . . ? C2 C3 C4 C40 179.6(3) . . . . ? C3 C4 C5 C6 -1.4(4) . . . . ? C40 C4 C5 C6 179.6(3) . . . . ? C4 C5 C6 C1 0.4(4) . . . . ? C2 C1 C6 C5 1.5(4) . . . . ? S1 C1 C6 C5 -176.4(2) . . . . ? C2 C1 S1 O2 4.8(2) . . . . ? C6 C1 S1 O2 -177.33(19) . . . . ? C2 C1 S1 O1 136.0(2) . . . . ? C6 C1 S1 O1 -46.2(2) . . . . ? C2 C1 S1 N1 -110.9(2) . . . . ? C6 C1 S1 N1 67.0(2) . . . . ? O2 S1 N1 C7 -57.8(2) . . . . ? O1 S1 N1 C7 174.13(17) . . . . ? C1 S1 N1 C7 58.2(2) . . . . ? S1 N1 C7 C8 -128.96(18) . . . . ? N1 C7 C8 C9 106.0(2) . . . . ? N1 C7 C8 C13 -70.7(3) . . . . ? C13 C8 C9 C10 -1.1(4) . . . . ? C7 C8 C9 C10 -177.9(2) . . . . ? C8 C9 C10 C11 1.3(4) . . . . ? C9 C10 C11 C12 -1.0(5) . . . . ? C10 C11 C12 C13 0.6(4) . . . . ? C11 C12 C13 C8 -0.5(3) . . . . ? C11 C12 C13 N2 -176.7(2) . . . . ? C9 C8 C13 C12 0.7(3) . . . . ? C7 C8 C13 C12 177.5(2) . . . . ? C9 C8 C13 N2 177.1(2) . . . . ? C7 C8 C13 N2 -6.1(3) . . . . ? C12 C13 N2 C14 -36.0(3) . . . . ? C8 C13 N2 C14 147.7(2) . . . . ? C13 N2 C14 C15 174.74(19) . . . . ? N2 C14 C15 C16 -175.8(2) . . . . ? N2 C14 C15 C20 2.3(4) . . . . ? C20 C15 C16 C17 -0.2(4) . . . . ? C14 C15 C16 C17 178.0(2) . . . . ? C15 C16 C17 C18 -0.2(4) . . . . ? C16 C17 C18 C19 0.3(4) . . . . ? C17 C18 C19 C20 0.0(4) . . . . ? C18 C19 C20 N3 -179.1(2) . . . . ? C18 C19 C20 C15 -0.3(4) . . . . ? C16 C15 C20 C19 0.4(3) . . . . ? C14 C15 C20 C19 -177.6(2) . . . . ? C16 C15 C20 N3 179.3(2) . . . . ? C14 C15 C20 N3 1.3(3) . . . . ? C19 C20 N3 S2 -28.7(3) . . . . ? C15 C20 N3 S2 152.43(19) . . . . ? C20 N3 S2 O3 61.5(2) . . . . ? C20 N3 S2 O4 -168.8(2) . . . . ? C20 N3 S2 C21 -54.1(2) . . . . ? O3 S2 C21 C26 168.06(18) . . . . ? O4 S2 C21 C26 36.7(2) . . . . ? N3 S2 C21 C26 -75.0(2) . . . . ? O3 S2 C21 C22 -12.3(2) . . . . ? O4 S2 C21 C22 -143.69(19) . . . . ? N3 S2 C21 C22 104.6(2) . . . . ? C26 C21 C22 C23 -0.8(3) . . . . ? S2 C21 C22 C23 179.6(2) . . . . ? C21 C22 C23 C24 0.1(4) . . . . ? C22 C23 C24 C25 0.3(4) . . . . ? C22 C23 C24 C240 179.3(3) . . . . ? C23 C24 C25 C26 0.0(4) . . . . ? C240 C24 C25 C26 -178.9(3) . . . . ? C24 C25 C26 C21 -0.8(4) . . . . ? C22 C21 C26 C25 1.2(3) . . . . ? S2 C21 C26 C25 -179.21(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3A N2 0.85(2) 1.95(2) 2.660(3) 141(2) . N1 H1A O1 0.80(2) 2.24(2) 3.038(3) 176(2) 3_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.219 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.044 # Attachment 'Ta.cif' data_Ta _database_code_depnum_ccdc_archive 'CCDC 646379' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H27 N3 O4 S2' _chemical_formula_sum 'C28 H27 N3 O4 S2' _chemical_formula_weight 533.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.797(5) _cell_length_b 10.788(4) _cell_length_c 14.713(8) _cell_angle_alpha 100.53(5) _cell_angle_beta 101.70(5) _cell_angle_gamma 100.23(6) _cell_volume 1310.4(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 18 _cell_measurement_theta_min 19.15 _cell_measurement_theta_max 45.08 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 2.169 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.2092 _exptl_absorpt_correction_T_max 0.3811 _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 7 Theta correction was applied. Weighted transmission curves were used. No Fourier smoothing was applied. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'MACH3 Enraf Nonius' _diffrn_measurement_method omega/2-theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 -1 7 -2 -4 2 3 -3 -2 _diffrn_standards_decay_% 18 _diffrn_reflns_number 5691 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0185 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 74.89 _reflns_number_total 5327 _reflns_number_gt 4401 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0938P)^2^+0.3226P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0047(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5327 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0636 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1561 _refine_ls_wR_factor_gt 0.1465 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7621(3) -0.1623(2) -0.33846(16) 0.0590(5) Uani 1 1 d . . . C2 C 0.8566(4) -0.0781(2) -0.3762(2) 0.0771(7) Uani 1 1 d . . . H2 H 0.8415 0.0054 -0.3743 0.092 Uiso 1 1 calc R . . C3 C 0.9723(3) -0.1186(3) -0.4162(2) 0.0763(7) Uani 1 1 d . . . H3 H 1.0360 -0.0612 -0.4406 0.092 Uiso 1 1 calc R . . C4 C 0.9967(3) -0.2426(2) -0.42144(16) 0.0639(6) Uani 1 1 d . . . C40 C 1.1269(4) -0.2836(4) -0.4645(2) 0.0931(9) Uani 1 1 d . . . H40A H 1.1049 -0.2804 -0.5306 0.140 Uiso 1 1 calc R . . H40B H 1.1312 -0.3703 -0.4590 0.140 Uiso 1 1 calc R . . H40C H 1.2273 -0.2263 -0.4314 0.140 Uiso 1 1 calc R . . C5 C 0.9009(3) -0.3248(2) -0.38479(18) 0.0695(6) Uani 1 1 d . . . H5 H 0.9143 -0.4090 -0.3882 0.083 Uiso 1 1 calc R . . C6 C 0.7853(3) -0.2859(2) -0.34301(17) 0.0652(6) Uani 1 1 d . . . H6 H 0.7230 -0.3432 -0.3179 0.078 Uiso 1 1 calc R . . S1 S 0.61687(7) -0.10996(7) -0.28349(5) 0.0750(2) Uani 1 1 d . . . O1 O 0.5540(3) -0.2120(2) -0.24328(18) 0.1050(8) Uani 1 1 d . . . O2 O 0.5125(3) -0.0615(3) -0.34914(16) 0.1174(9) Uani 1 1 d . . . N1 N 0.7076(2) 0.0139(2) -0.19779(14) 0.0613(5) Uani 1 1 d . . . C7 C 0.8354(2) -0.0012(2) -0.12216(15) 0.0549(5) Uani 1 1 d . . . H7A H 0.9349 0.0537 -0.1232 0.066 Uiso 1 1 calc R . . H7B H 0.8468 -0.0901 -0.1349 0.066 Uiso 1 1 calc R . . C8 C 0.8051(2) 0.03304(19) -0.02427(15) 0.0516(4) Uani 1 1 d . . . C9 C 0.7044(3) -0.0568(2) 0.00554(19) 0.0707(7) Uani 1 1 d . . . H9 H 0.6554 -0.1365 -0.0357 0.085 Uiso 1 1 calc R . . C10 C 0.6752(3) -0.0308(3) 0.0949(2) 0.0787(8) Uani 1 1 d . . . H10 H 0.6085 -0.0931 0.1137 0.094 Uiso 1 1 calc R . . C11 C 0.7447(3) 0.0871(2) 0.15634(18) 0.0663(6) Uani 1 1 d . . . H11 H 0.7236 0.1052 0.2162 0.080 Uiso 1 1 calc R . . C12 C 0.8455(3) 0.1785(2) 0.12915(16) 0.0580(5) Uani 1 1 d . . . H12 H 0.8925 0.2582 0.1709 0.070 Uiso 1 1 calc R . . C13 C 0.8776(2) 0.15224(18) 0.03920(14) 0.0482(4) Uani 1 1 d . . . N2 N 0.97891(19) 0.24403(15) 0.00729(12) 0.0495(4) Uani 1 1 d . . . C14 C 1.0905(2) 0.33080(19) 0.06743(15) 0.0535(5) Uani 1 1 d . . . H14 H 1.1066 0.3284 0.1315 0.064 Uiso 1 1 calc R . . C15 C 1.1938(2) 0.43302(19) 0.04158(15) 0.0517(4) Uani 1 1 d . . . C16 C 1.3059(3) 0.5245(2) 0.11499(18) 0.0686(6) Uani 1 1 d . . . H16 H 1.3146 0.5161 0.1775 0.082 Uiso 1 1 calc R . . C17 C 1.4038(3) 0.6265(3) 0.0970(2) 0.0795(8) Uani 1 1 d . . . H17 H 1.4772 0.6871 0.1468 0.095 Uiso 1 1 calc R . . C18 C 1.3922(3) 0.6379(2) 0.0049(2) 0.0747(7) Uani 1 1 d . . . H18 H 1.4587 0.7067 -0.0075 0.090 Uiso 1 1 calc R . . C19 C 1.2836(3) 0.5493(2) -0.07015(18) 0.0651(6) Uani 1 1 d . . . H19 H 1.2780 0.5582 -0.1323 0.078 Uiso 1 1 calc R . . C20 C 1.1828(2) 0.44656(18) -0.05236(15) 0.0508(4) Uani 1 1 d . . . N3 N 1.0711(2) 0.35193(18) -0.12506(13) 0.0602(5) Uani 1 1 d . . . S2 S 1.00965(6) 0.35355(5) -0.23553(4) 0.05443(17) Uani 1 1 d . . . O3 O 0.88300(19) 0.24019(15) -0.27180(11) 0.0658(4) Uani 1 1 d . . . O4 O 0.9767(2) 0.47619(16) -0.24561(13) 0.0700(4) Uani 1 1 d . . . C21 C 1.1667(3) 0.3328(2) -0.28896(15) 0.0587(5) Uani 1 1 d . . . C22 C 1.2428(3) 0.4335(3) -0.3222(2) 0.0769(7) Uani 1 1 d . . . H22 H 1.2120 0.5121 -0.3152 0.092 Uiso 1 1 calc R . . C23 C 1.3641(4) 0.4152(4) -0.3655(2) 0.0928(10) Uani 1 1 d . . . H23 H 1.4151 0.4827 -0.3875 0.111 Uiso 1 1 calc R . . C24 C 1.4121(3) 0.3003(4) -0.3771(2) 0.0938(11) Uani 1 1 d . . . C240 C 1.5469(4) 0.2817(6) -0.4242(3) 0.143(2) Uani 1 1 d . . . H24A H 1.6451 0.3357 -0.3843 0.214 Uiso 1 1 calc R . . H24B H 1.5265 0.3048 -0.4848 0.214 Uiso 1 1 calc R . . H24C H 1.5545 0.1928 -0.4334 0.214 Uiso 1 1 calc R . . C25 C 1.3351(4) 0.2011(4) -0.3439(2) 0.0927(10) Uani 1 1 d . . . H25 H 1.3662 0.1226 -0.3518 0.111 Uiso 1 1 calc R . . C26 C 1.2125(3) 0.2155(3) -0.29903(19) 0.0732(7) Uani 1 1 d . . . H26 H 1.1625 0.1483 -0.2764 0.088 Uiso 1 1 calc R . . H3A H 1.016(4) 0.297(3) -0.106(2) 0.097(10) Uiso 1 1 d . . . H1A H 0.724(4) 0.079(3) -0.219(2) 0.088(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0540(11) 0.0569(11) 0.0537(11) -0.0034(9) 0.0051(9) 0.0063(9) C2 0.0848(17) 0.0543(13) 0.0922(19) 0.0112(12) 0.0278(15) 0.0139(12) C3 0.0784(17) 0.0717(15) 0.0801(17) 0.0171(13) 0.0307(14) 0.0069(13) C4 0.0608(13) 0.0749(14) 0.0502(11) 0.0030(10) 0.0106(10) 0.0153(11) C40 0.0790(18) 0.121(3) 0.0788(18) 0.0026(17) 0.0267(15) 0.0324(18) C5 0.0822(16) 0.0634(13) 0.0651(14) 0.0101(11) 0.0186(12) 0.0257(12) C6 0.0696(14) 0.0596(12) 0.0626(13) 0.0092(10) 0.0185(11) 0.0065(10) S1 0.0484(3) 0.0827(4) 0.0737(4) -0.0174(3) 0.0074(3) 0.0074(3) O1 0.0814(13) 0.0818(13) 0.1307(18) -0.0195(12) 0.0533(13) -0.0228(10) O2 0.0791(13) 0.163(2) 0.0870(14) -0.0234(14) -0.0155(11) 0.0608(15) N1 0.0597(11) 0.0580(11) 0.0592(11) 0.0013(9) 0.0096(8) 0.0129(8) C7 0.0493(10) 0.0514(10) 0.0577(11) 0.0040(9) 0.0133(9) 0.0034(8) C8 0.0456(10) 0.0490(10) 0.0577(11) 0.0105(8) 0.0152(8) 0.0030(8) C9 0.0671(14) 0.0595(13) 0.0748(15) 0.0086(11) 0.0227(12) -0.0134(11) C10 0.0757(16) 0.0778(16) 0.0771(16) 0.0209(13) 0.0309(13) -0.0151(13) C11 0.0639(13) 0.0760(15) 0.0647(13) 0.0190(11) 0.0308(11) 0.0096(11) C12 0.0586(12) 0.0571(11) 0.0574(12) 0.0090(9) 0.0213(9) 0.0065(9) C13 0.0428(9) 0.0473(9) 0.0547(10) 0.0122(8) 0.0157(8) 0.0050(7) N2 0.0490(8) 0.0433(8) 0.0550(9) 0.0084(7) 0.0187(7) 0.0029(6) C14 0.0546(11) 0.0504(10) 0.0528(11) 0.0092(8) 0.0159(9) 0.0045(8) C15 0.0457(10) 0.0472(10) 0.0578(11) 0.0068(8) 0.0138(8) 0.0029(8) C16 0.0595(13) 0.0689(14) 0.0628(13) 0.0063(11) 0.0087(10) -0.0075(11) C17 0.0653(15) 0.0697(15) 0.0784(17) 0.0004(12) 0.0067(12) -0.0205(12) C18 0.0618(14) 0.0606(13) 0.0871(18) 0.0113(12) 0.0169(12) -0.0170(11) C19 0.0628(13) 0.0573(12) 0.0684(14) 0.0123(10) 0.0204(11) -0.0078(10) C20 0.0456(10) 0.0435(9) 0.0593(11) 0.0069(8) 0.0160(8) 0.0008(7) N3 0.0681(11) 0.0502(9) 0.0514(10) 0.0096(7) 0.0135(8) -0.0114(8) S2 0.0540(3) 0.0501(3) 0.0566(3) 0.0122(2) 0.0133(2) 0.0051(2) O3 0.0580(9) 0.0621(9) 0.0642(9) 0.0085(7) 0.0065(7) -0.0046(7) O4 0.0739(10) 0.0593(9) 0.0862(11) 0.0260(8) 0.0273(9) 0.0202(8) C21 0.0545(11) 0.0669(13) 0.0508(11) 0.0105(9) 0.0093(9) 0.0105(10) C22 0.0730(16) 0.0894(18) 0.0767(16) 0.0311(14) 0.0293(13) 0.0148(13) C23 0.0687(17) 0.137(3) 0.0758(18) 0.0302(18) 0.0268(14) 0.0149(18) C24 0.0541(14) 0.158(3) 0.0558(14) 0.0009(17) 0.0059(11) 0.0229(18) C240 0.0689(19) 0.266(6) 0.080(2) -0.006(3) 0.0175(17) 0.053(3) C25 0.0700(17) 0.116(3) 0.0771(18) -0.0158(17) 0.0007(14) 0.0399(17) C26 0.0645(14) 0.0759(16) 0.0700(15) 0.0026(12) 0.0066(11) 0.0176(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.377(3) . ? C1 C2 1.388(4) . ? C1 S1 1.764(3) . ? C2 C3 1.371(4) . ? C2 H2 0.9300 . ? C3 C4 1.383(4) . ? C3 H3 0.9300 . ? C4 C5 1.371(4) . ? C4 C40 1.510(4) . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? C5 C6 1.378(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? S1 O1 1.422(3) . ? S1 O2 1.430(3) . ? S1 N1 1.615(2) . ? N1 C7 1.467(3) . ? N1 H1A 0.82(3) . ? C7 C8 1.510(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.388(3) . ? C8 C13 1.400(3) . ? C9 C10 1.379(4) . ? C9 H9 0.9300 . ? C10 C11 1.374(4) . ? C10 H10 0.9300 . ? C11 C12 1.377(3) . ? C11 H11 0.9300 . ? C12 C13 1.398(3) . ? C12 H12 0.9300 . ? C13 N2 1.422(2) . ? N2 C14 1.281(3) . ? C14 C15 1.457(3) . ? C14 H14 0.9300 . ? C15 C16 1.395(3) . ? C15 C20 1.402(3) . ? C16 C17 1.373(3) . ? C16 H16 0.9300 . ? C17 C18 1.368(4) . ? C17 H17 0.9300 . ? C18 C19 1.381(3) . ? C18 H18 0.9300 . ? C19 C20 1.391(3) . ? C19 H19 0.9300 . ? C20 N3 1.404(3) . ? N3 S2 1.610(2) . ? N3 H3A 0.83(3) . ? S2 O4 1.4308(17) . ? S2 O3 1.4346(19) . ? S2 C21 1.750(3) . ? C21 C26 1.386(4) . ? C21 C22 1.391(3) . ? C22 C23 1.374(4) . ? C22 H22 0.9300 . ? C23 C24 1.372(5) . ? C23 H23 0.9300 . ? C24 C25 1.382(5) . ? C24 C240 1.514(4) . ? C240 H24A 0.9600 . ? C240 H24B 0.9600 . ? C240 H24C 0.9600 . ? C25 C26 1.391(4) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 119.1(2) . . ? C6 C1 S1 120.6(2) . . ? C2 C1 S1 120.25(19) . . ? C3 C2 C1 119.8(2) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 121.7(3) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C5 C4 C3 117.7(2) . . ? C5 C4 C40 121.8(3) . . ? C3 C4 C40 120.5(3) . . ? C4 C40 H40A 109.5 . . ? C4 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C4 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C4 C5 C6 121.7(2) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C1 C6 C5 120.0(2) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? O1 S1 O2 120.01(17) . . ? O1 S1 N1 108.38(14) . . ? O2 S1 N1 105.08(14) . . ? O1 S1 C1 106.55(13) . . ? O2 S1 C1 108.97(14) . . ? N1 S1 C1 107.27(11) . . ? C7 N1 S1 118.66(17) . . ? C7 N1 H1A 117(2) . . ? S1 N1 H1A 110(2) . . ? N1 C7 C8 112.85(18) . . ? N1 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? N1 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C9 C8 C13 118.1(2) . . ? C9 C8 C7 119.47(19) . . ? C13 C8 C7 122.37(18) . . ? C10 C9 C8 121.5(2) . . ? C10 C9 H9 119.2 . . ? C8 C9 H9 119.2 . . ? C11 C10 C9 120.0(2) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 120.0(2) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C13 120.4(2) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C8 119.90(19) . . ? C12 C13 N2 122.53(18) . . ? C8 C13 N2 117.55(18) . . ? C14 N2 C13 120.32(18) . . ? N2 C14 C15 123.99(19) . . ? N2 C14 H14 118.0 . . ? C15 C14 H14 118.0 . . ? C16 C15 C20 118.55(19) . . ? C16 C15 C14 117.8(2) . . ? C20 C15 C14 123.59(18) . . ? C17 C16 C15 121.5(2) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C18 C17 C16 119.2(2) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C17 C18 C19 121.3(2) . . ? C17 C18 H18 119.3 . . ? C19 C18 H18 119.3 . . ? C18 C19 C20 119.8(2) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C19 C20 C15 119.6(2) . . ? C19 C20 N3 122.9(2) . . ? C15 C20 N3 117.42(17) . . ? C20 N3 S2 128.81(16) . . ? C20 N3 H3A 114(2) . . ? S2 N3 H3A 116(2) . . ? O4 S2 O3 118.70(11) . . ? O4 S2 N3 111.14(12) . . ? O3 S2 N3 103.71(11) . . ? O4 S2 C21 107.13(12) . . ? O3 S2 C21 108.96(12) . . ? N3 S2 C21 106.62(12) . . ? C26 C21 C22 120.6(2) . . ? C26 C21 S2 119.7(2) . . ? C22 C21 S2 119.7(2) . . ? C23 C22 C21 119.1(3) . . ? C23 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? C24 C23 C22 121.8(3) . . ? C24 C23 H23 119.1 . . ? C22 C23 H23 119.1 . . ? C23 C24 C25 118.3(3) . . ? C23 C24 C240 121.4(4) . . ? C25 C24 C240 120.3(4) . . ? C24 C240 H24A 109.5 . . ? C24 C240 H24B 109.5 . . ? H24A C240 H24B 109.5 . . ? C24 C240 H24C 109.5 . . ? H24A C240 H24C 109.5 . . ? H24B C240 H24C 109.5 . . ? C24 C25 C26 121.8(3) . . ? C24 C25 H25 119.1 . . ? C26 C25 H25 119.1 . . ? C21 C26 C25 118.3(3) . . ? C21 C26 H26 120.9 . . ? C25 C26 H26 120.9 . . ? 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 C6 C1 C2 C3 -0.7(4) . . . . ? S1 C1 C2 C3 178.1(2) . . . . ? C1 C2 C3 C4 0.9(4) . . . . ? C2 C3 C4 C5 -0.1(4) . . . . ? C2 C3 C4 C40 -179.0(3) . . . . ? C3 C4 C5 C6 -0.8(4) . . . . ? C40 C4 C5 C6 178.1(2) . . . . ? C2 C1 C6 C5 -0.1(4) . . . . ? S1 C1 C6 C5 -178.96(18) . . . . ? C4 C5 C6 C1 0.9(4) . . . . ? C6 C1 S1 O1 5.2(2) . . . . ? C2 C1 S1 O1 -173.6(2) . . . . ? C6 C1 S1 O2 -125.6(2) . . . . ? C2 C1 S1 O2 55.6(2) . . . . ? C6 C1 S1 N1 121.1(2) . . . . ? C2 C1 S1 N1 -57.7(2) . . . . ? O1 S1 N1 C7 56.2(2) . . . . ? O2 S1 N1 C7 -174.35(19) . . . . ? C1 S1 N1 C7 -58.5(2) . . . . ? S1 N1 C7 C8 -122.23(18) . . . . ? N1 C7 C8 C9 80.8(3) . . . . ? N1 C7 C8 C13 -100.5(2) . . . . ? C13 C8 C9 C10 0.1(4) . . . . ? C7 C8 C9 C10 178.9(3) . . . . ? C8 C9 C10 C11 1.0(5) . . . . ? C9 C10 C11 C12 -1.1(4) . . . . ? C10 C11 C12 C13 0.1(4) . . . . ? C11 C12 C13 C8 0.9(3) . . . . ? C11 C12 C13 N2 179.1(2) . . . . ? C9 C8 C13 C12 -1.0(3) . . . . ? C7 C8 C13 C12 -179.8(2) . . . . ? C9 C8 C13 N2 -179.2(2) . . . . ? C7 C8 C13 N2 2.0(3) . . . . ? C12 C13 N2 C14 27.4(3) . . . . ? C8 C13 N2 C14 -154.5(2) . . . . ? C13 N2 C14 C15 -176.30(18) . . . . ? N2 C14 C15 C16 177.2(2) . . . . ? N2 C14 C15 C20 -0.6(3) . . . . ? C20 C15 C16 C17 0.3(4) . . . . ? C14 C15 C16 C17 -177.6(3) . . . . ? C15 C16 C17 C18 -0.7(4) . . . . ? C16 C17 C18 C19 0.3(5) . . . . ? C17 C18 C19 C20 0.5(4) . . . . ? C18 C19 C20 C15 -0.8(4) . . . . ? C18 C19 C20 N3 -179.1(2) . . . . ? C16 C15 C20 C19 0.4(3) . . . . ? C14 C15 C20 C19 178.3(2) . . . . ? C16 C15 C20 N3 178.8(2) . . . . ? C14 C15 C20 N3 -3.3(3) . . . . ? C19 C20 N3 S2 -13.4(3) . . . . ? C15 C20 N3 S2 168.22(18) . . . . ? C20 N3 S2 O4 -44.3(2) . . . . ? C20 N3 S2 O3 -173.0(2) . . . . ? C20 N3 S2 C21 72.1(2) . . . . ? O4 S2 C21 C26 -172.96(19) . . . . ? O3 S2 C21 C26 -43.4(2) . . . . ? N3 S2 C21 C26 68.0(2) . . . . ? O4 S2 C21 C22 6.1(2) . . . . ? O3 S2 C21 C22 135.7(2) . . . . ? N3 S2 C21 C22 -113.0(2) . . . . ? C26 C21 C22 C23 0.2(4) . . . . ? S2 C21 C22 C23 -178.9(2) . . . . ? C21 C22 C23 C24 0.2(5) . . . . ? C22 C23 C24 C25 -0.1(4) . . . . ? C22 C23 C24 C240 -179.5(3) . . . . ? C23 C24 C25 C26 -0.4(4) . . . . ? C240 C24 C25 C26 179.0(3) . . . . ? C22 C21 C26 C25 -0.6(4) . . . . ? S2 C21 C26 C25 178.46(19) . . . . ? C24 C25 C26 C21 0.7(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3A N2 0.83(3) 1.92(3) 2.634(3) 144(3) . N1 H1A O3 0.82(3) 2.38(3) 3.137(3) 154(3) . _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 74.89 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.288 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.064 # Attachment 'Tc_new.cif' data_Tc _database_code_depnum_ccdc_archive 'CCDC 646380' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H27 N3 O4 S2' _chemical_formula_sum 'C28 H27 N3 O4 S2' _chemical_formula_weight 533.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.2059(6) _cell_length_b 10.7345(5) _cell_length_c 12.8784(5) _cell_angle_alpha 97.962(4) _cell_angle_beta 95.360(5) _cell_angle_gamma 108.697(5) _cell_volume 1309.19(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 21.21 _cell_measurement_theta_max 42.39 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.44 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 2.171 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.2157 _exptl_absorpt_correction_T_max 0.3830 _exptl_absorpt_process_details ? _exptl_special_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 7 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CAD4 Enraf Nonius' _diffrn_measurement_method omega/2-theta _diffrn_detector_area_resol_mean ? _diffrn_standars_number 3 _diffrn_standards_interval_count ? _diffrn_standars_interval_time '120 min' _diffrn_standards_decay_% 10 _diffrn_reflns_number 5742 _diffrn_reflns_av_R_equivalents 0.0973 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 73.45 _reflns_number_total 5263 _reflns_number_gt 4931 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SIR-92 (Altomare, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1074P)^2^+0.5595P] 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 SHELXL _refine_ls_extinction_coef 0.0215(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5263 _refine_ls_number_parameters 337 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0555 _refine_ls_wR_factor_ref 0.1627 _refine_ls_wR_factor_gt 0.1596 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 C1 C 0.4455(2) 0.70395(19) 0.39355(15) 0.0348(4) Uani 1 1 d . . . C2 C 0.4393(3) 0.5728(2) 0.37034(18) 0.0458(5) Uani 1 1 d . . . H2 H 0.5000 0.5424 0.4098 0.055 Uiso 1 1 calc R . . C3 C 0.3414(3) 0.4865(2) 0.2872(2) 0.0561(6) Uani 1 1 d . . . H3A H 0.3371 0.3980 0.2711 0.067 Uiso 1 1 calc R . . C4 C 0.2506(3) 0.5304(2) 0.22844(18) 0.0501(6) Uani 1 1 d . . . C40 C 0.1444(4) 0.4360(3) 0.1382(2) 0.0794(10) Uani 1 1 d . . . H40A H 0.1219 0.4860 0.0871 0.119 Uiso 1 1 calc R . . H40B H 0.0612 0.3896 0.1651 0.119 Uiso 1 1 calc R . . H40C H 0.1826 0.3725 0.1050 0.119 Uiso 1 1 calc R . . C5 C 0.2582(3) 0.6621(3) 0.2538(2) 0.0576(7) Uani 1 1 d . . . H5 H 0.1971 0.6925 0.2148 0.069 Uiso 1 1 calc R . . C6 C 0.3548(3) 0.7496(2) 0.3358(2) 0.0532(6) Uani 1 1 d . . . H6 H 0.3587 0.8380 0.3520 0.064 Uiso 1 1 calc R . . S1 S 0.56832(5) 0.81530(5) 0.49907(4) 0.03634(18) Uani 1 1 d . . . O1 O 0.65199(17) 0.74432(17) 0.54078(12) 0.0491(4) Uani 1 1 d . . . O2 O 0.63462(18) 0.93836(16) 0.46312(13) 0.0497(4) Uani 1 1 d . . . N1 N 0.4822(2) 0.85374(17) 0.59058(14) 0.0427(4) Uani 1 1 d . . . H1 H 0.4474 0.9242 0.5701 0.100 Uiso 1 1 d . . . C7 C 0.3966(3) 0.7472(2) 0.64191(17) 0.0445(5) Uani 1 1 d . . . H7A H 0.4450 0.7520 0.7116 0.053 Uiso 1 1 calc R . . H7B H 0.3836 0.6606 0.6001 0.053 Uiso 1 1 calc R . . C8 C 0.2567(2) 0.7616(2) 0.65212(16) 0.0404(5) Uani 1 1 d . . . C9 C 0.1354(3) 0.6739(2) 0.5892(2) 0.0589(7) Uani 1 1 d . . . H9 H 0.1414 0.6058 0.5387 0.071 Uiso 1 1 calc R . . C10 C 0.0060(3) 0.6852(3) 0.5995(2) 0.0655(8) Uani 1 1 d . . . H10 H -0.0736 0.6248 0.5566 0.079 Uiso 1 1 calc R . . C11 C -0.0049(3) 0.7855(3) 0.6730(2) 0.0590(7) Uani 1 1 d . . . H11 H -0.0920 0.7929 0.6802 0.071 Uiso 1 1 calc R . . C12 C 0.1136(2) 0.8754(2) 0.73618(19) 0.0476(5) Uani 1 1 d . . . H12 H 0.1059 0.9430 0.7863 0.057 Uiso 1 1 calc R . . C13 C 0.2453(2) 0.86550(19) 0.72515(15) 0.0365(4) Uani 1 1 d . . . N2 N 0.36979(17) 0.95281(17) 0.78961(13) 0.0355(4) Uani 1 1 d . . . C14 C 0.3777(2) 1.0695(2) 0.83227(17) 0.0399(4) Uani 1 1 d . . . H14 H 0.3042 1.0992 0.8132 0.048 Uiso 1 1 calc R . . C15 C 0.4958(2) 1.1601(2) 0.90968(17) 0.0382(4) Uani 1 1 d . . . C16 C 0.4810(3) 1.2771(2) 0.9602(2) 0.0570(6) Uani 1 1 d . . . H16 H 0.4009 1.2968 0.9402 0.068 Uiso 1 1 calc R . . C17 C 0.5824(3) 1.3649(2) 1.0395(2) 0.0636(7) Uani 1 1 d . . . H17 H 0.5701 1.4418 1.0734 0.076 Uiso 1 1 calc R . . C18 C 0.7018(3) 1.3365(2) 1.0672(2) 0.0535(6) Uani 1 1 d . . . H18 H 0.7710 1.3955 1.1199 0.064 Uiso 1 1 calc R . . C19 C 0.7207(2) 1.2224(2) 1.01857(18) 0.0443(5) Uani 1 1 d . . . H19 H 0.8022 1.2052 1.0387 0.053 Uiso 1 1 calc R . . C20 C 0.6187(2) 1.13255(19) 0.93935(15) 0.0351(4) Uani 1 1 d . . . N3 N 0.62983(19) 1.01358(19) 0.88782(16) 0.0449(4) Uani 1 1 d . . . H3 H 0.5517 0.9552 0.8436 0.100 Uiso 1 1 d . . . S2 S 0.76593(5) 0.96617(5) 0.89343(4) 0.04103(19) Uani 1 1 d . . . O3 O 0.71764(19) 0.83661(16) 0.82905(16) 0.0577(5) Uani 1 1 d . . . O4 O 0.82666(18) 0.98418(18) 1.00173(13) 0.0527(4) Uani 1 1 d . . . C21 C 0.8884(2) 1.0757(2) 0.83108(16) 0.0381(4) Uani 1 1 d . . . C22 C 0.8713(3) 1.0593(2) 0.72114(18) 0.0502(6) Uani 1 1 d . . . H22 H 0.7955 0.9909 0.6806 0.060 Uiso 1 1 calc R . . C23 C 0.9676(3) 1.1453(3) 0.67243(19) 0.0585(6) Uani 1 1 d . . . H23 H 0.9566 1.1335 0.5988 0.070 Uiso 1 1 calc R . . C24 C 1.0807(3) 1.2492(3) 0.7316(2) 0.0547(6) Uani 1 1 d . . . C240 C 1.1860(4) 1.3454(4) 0.6792(3) 0.0915(11) Uani 1 1 d . . . H24A H 1.1946 1.2999 0.6120 0.137 Uiso 1 1 calc R . . H24B H 1.2752 1.3784 0.7238 0.137 Uiso 1 1 calc R . . H24C H 1.1550 1.4189 0.6688 0.137 Uiso 1 1 calc R . . C25 C 1.0952(2) 1.2641(2) 0.84117(19) 0.0484(5) Uani 1 1 d . . . H25 H 1.1698 1.3337 0.8817 0.058 Uiso 1 1 calc R . . C26 C 1.0013(2) 1.1779(2) 0.89156(16) 0.0415(5) Uani 1 1 d . . . H26 H 1.0137 1.1883 0.9651 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0440(10) 0.0299(9) 0.0302(9) -0.0008(7) 0.0000(7) 0.0160(8) C2 0.0565(13) 0.0318(10) 0.0468(11) -0.0022(8) -0.0099(10) 0.0204(9) C3 0.0728(16) 0.0289(10) 0.0571(14) -0.0095(9) -0.0116(12) 0.0173(11) C4 0.0610(14) 0.0398(11) 0.0366(11) -0.0019(9) -0.0080(10) 0.0071(10) C40 0.091(2) 0.0576(17) 0.0610(17) -0.0070(13) -0.0317(16) 0.0056(16) C5 0.0689(16) 0.0486(13) 0.0510(13) 0.0036(10) -0.0205(12) 0.0243(12) C6 0.0691(16) 0.0351(11) 0.0525(13) -0.0023(9) -0.0174(11) 0.0251(11) S1 0.0410(3) 0.0302(3) 0.0346(3) -0.00347(18) -0.00337(19) 0.0140(2) O1 0.0517(9) 0.0504(9) 0.0452(8) -0.0025(7) -0.0107(7) 0.0269(7) O2 0.0535(9) 0.0360(8) 0.0533(9) 0.0023(7) 0.0043(7) 0.0096(7) N1 0.0575(11) 0.0306(8) 0.0397(9) -0.0020(7) 0.0058(8) 0.0185(8) C7 0.0649(14) 0.0346(10) 0.0393(10) 0.0038(8) 0.0088(9) 0.0246(10) C8 0.0537(12) 0.0312(9) 0.0334(9) 0.0022(8) -0.0005(8) 0.0138(9) C9 0.0748(17) 0.0394(12) 0.0484(13) -0.0116(10) -0.0081(12) 0.0129(12) C10 0.0562(15) 0.0485(14) 0.0680(17) -0.0103(12) -0.0220(13) 0.0025(12) C11 0.0426(13) 0.0547(15) 0.0689(16) -0.0012(12) -0.0126(11) 0.0125(11) C12 0.0402(11) 0.0438(12) 0.0504(12) -0.0061(9) -0.0080(9) 0.0128(9) C13 0.0395(10) 0.0326(9) 0.0331(9) 0.0002(7) -0.0055(7) 0.0118(8) N2 0.0348(8) 0.0363(8) 0.0323(8) -0.0035(6) -0.0033(6) 0.0139(7) C14 0.0350(10) 0.0358(10) 0.0461(11) -0.0013(8) -0.0067(8) 0.0152(8) C15 0.0370(10) 0.0298(9) 0.0443(10) -0.0011(8) -0.0035(8) 0.0126(8) C16 0.0486(13) 0.0392(12) 0.0780(17) -0.0110(11) -0.0108(12) 0.0223(10) C17 0.0625(15) 0.0356(12) 0.0817(19) -0.0214(12) -0.0110(13) 0.0209(11) C18 0.0543(13) 0.0375(11) 0.0541(13) -0.0116(10) -0.0116(10) 0.0091(10) C19 0.0417(11) 0.0412(11) 0.0445(11) -0.0028(9) -0.0090(9) 0.0151(9) C20 0.0359(9) 0.0304(9) 0.0365(9) 0.0007(7) -0.0008(7) 0.0118(8) N3 0.0367(9) 0.0393(9) 0.0540(11) -0.0111(8) -0.0092(8) 0.0187(8) S2 0.0399(3) 0.0351(3) 0.0497(3) 0.0016(2) -0.0037(2) 0.0202(2) O3 0.0552(10) 0.0336(8) 0.0818(12) -0.0053(8) 0.0037(9) 0.0200(7) O4 0.0506(9) 0.0634(11) 0.0506(9) 0.0181(8) -0.0028(7) 0.0277(8) C21 0.0381(10) 0.0386(10) 0.0388(10) -0.0008(8) -0.0072(8) 0.0216(8) C22 0.0560(13) 0.0498(13) 0.0393(11) -0.0061(9) -0.0132(9) 0.0218(11) C23 0.0757(17) 0.0677(16) 0.0349(11) 0.0033(11) 0.0015(11) 0.0324(14) C24 0.0592(14) 0.0602(15) 0.0519(13) 0.0125(11) 0.0099(11) 0.0282(12) C240 0.094(3) 0.101(3) 0.078(2) 0.028(2) 0.033(2) 0.020(2) C25 0.0430(11) 0.0488(13) 0.0500(12) 0.0029(10) -0.0044(9) 0.0164(10) C26 0.0416(11) 0.0457(11) 0.0355(10) -0.0003(8) -0.0078(8) 0.0194(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.377(3) . ? C1 C6 1.383(3) . ? C1 S1 1.766(2) . ? C2 C3 1.391(3) . ? C2 H2 0.9300 . ? C3 C4 1.378(4) . ? C3 H3A 0.9300 . ? C4 C5 1.382(3) . ? C4 C40 1.512(3) . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? C5 C6 1.381(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? S1 O1 1.4294(16) . ? S1 O2 1.4395(17) . ? S1 N1 1.6194(18) . ? N1 C7 1.478(3) . ? N1 H1 0.9890 . ? C7 C8 1.500(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.390(3) . ? C8 C13 1.399(3) . ? C9 C10 1.380(4) . ? C9 H9 0.9300 . ? C10 C11 1.372(4) . ? C10 H10 0.9300 . ? C11 C12 1.381(3) . ? C11 H11 0.9300 . ? C12 C13 1.400(3) . ? C12 H12 0.9300 . ? C13 N2 1.416(2) . ? N2 C14 1.271(3) . ? C14 C15 1.465(3) . ? C14 H14 0.9300 . ? C15 C16 1.392(3) . ? C15 C20 1.410(3) . ? C16 C17 1.383(3) . ? C16 H16 0.9300 . ? C17 C18 1.376(4) . ? C17 H17 0.9300 . ? C18 C19 1.375(3) . ? C18 H18 0.9300 . ? C19 C20 1.393(3) . ? C19 H19 0.9300 . ? C20 N3 1.399(3) . ? N3 S2 1.6242(18) . ? N3 H3 0.9213 . ? S2 O3 1.4246(17) . ? S2 O4 1.4332(17) . ? S2 C21 1.760(2) . ? C21 C26 1.386(3) . ? C21 C22 1.390(3) . ? C22 C23 1.380(4) . ? C22 H22 0.9300 . ? C23 C24 1.390(4) . ? C23 H23 0.9300 . ? C24 C25 1.386(4) . ? C24 C240 1.515(4) . ? C240 H24A 0.9600 . ? C240 H24B 0.9600 . ? C240 H24C 0.9600 . ? C25 C26 1.382(3) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? 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 C2 C1 C6 120.67(19) . . ? C2 C1 S1 120.11(16) . . ? C6 C1 S1 119.22(16) . . ? C1 C2 C3 119.2(2) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C4 C3 C2 120.9(2) . . ? C4 C3 H3A 119.5 . . ? C2 C3 H3A 119.5 . . ? C3 C4 C5 118.7(2) . . ? C3 C4 C40 120.7(2) . . ? C5 C4 C40 120.6(2) . . ? C4 C40 H40A 109.5 . . ? C4 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C4 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C6 C5 C4 121.4(2) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C1 119.1(2) . . ? C5 C6 H6 120.5 . . ? C1 C6 H6 120.5 . . ? O1 S1 O2 119.66(11) . . ? O1 S1 N1 108.00(10) . . ? O2 S1 N1 105.28(10) . . ? O1 S1 C1 107.33(9) . . ? O2 S1 C1 108.44(10) . . ? N1 S1 C1 107.60(10) . . ? C7 N1 S1 119.20(13) . . ? C7 N1 H1 121.2 . . ? S1 N1 H1 107.5 . . ? N1 C7 C8 110.70(17) . . ? N1 C7 H7A 109.5 . . ? C8 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C9 C8 C13 118.0(2) . . ? C9 C8 C7 121.5(2) . . ? C13 C8 C7 120.51(19) . . ? C10 C9 C8 121.7(2) . . ? C10 C9 H9 119.1 . . ? C8 C9 H9 119.1 . . ? C11 C10 C9 120.0(2) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 120.0(3) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C13 120.3(2) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C8 C13 C12 119.95(19) . . ? C8 C13 N2 117.20(19) . . ? C12 C13 N2 122.75(18) . . ? C14 N2 C13 120.40(17) . . ? N2 C14 C15 123.84(18) . . ? N2 C14 H14 118.1 . . ? C15 C14 H14 118.1 . . ? C16 C15 C20 118.69(19) . . ? C16 C15 C14 117.12(19) . . ? C20 C15 C14 124.11(18) . . ? C17 C16 C15 121.6(2) . . ? C17 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C18 C17 C16 118.9(2) . . ? C18 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? C19 C18 C17 121.2(2) . . ? C19 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? C18 C19 C20 120.5(2) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C19 C20 N3 123.56(19) . . ? C19 C20 C15 119.10(18) . . ? N3 C20 C15 117.33(17) . . ? C20 N3 S2 127.98(15) . . ? C20 N3 H3 116.9 . . ? S2 N3 H3 115.1 . . ? O3 S2 O4 120.00(11) . . ? O3 S2 N3 104.23(10) . . ? O4 S2 N3 109.83(10) . . ? O3 S2 C21 108.67(11) . . ? O4 S2 C21 107.32(10) . . ? N3 S2 C21 106.00(10) . . ? C26 C21 C22 120.3(2) . . ? C26 C21 S2 120.03(16) . . ? C22 C21 S2 119.70(17) . . ? C23 C22 C21 119.6(2) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C22 C23 C24 121.1(2) . . ? C22 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? C25 C24 C23 118.3(2) . . ? C25 C24 C240 120.0(3) . . ? C23 C24 C240 121.6(3) . . ? C24 C240 H24A 109.5 . . ? C24 C240 H24B 109.5 . . ? H24A C240 H24B 109.5 . . ? C24 C240 H24C 109.5 . . ? H24A C240 H24C 109.5 . . ? H24B C240 H24C 109.5 . . ? C26 C25 C24 121.6(2) . . ? C26 C25 H25 119.2 . . ? C24 C25 H25 119.2 . . ? C25 C26 C21 119.2(2) . . ? C25 C26 H26 120.4 . . ? C21 C26 H26 120.4 . . ? 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 C6 C1 C2 C3 0.6(4) . . . . ? S1 C1 C2 C3 179.7(2) . . . . ? C1 C2 C3 C4 -0.2(4) . . . . ? C2 C3 C4 C5 -0.2(4) . . . . ? C2 C3 C4 C40 180.0(3) . . . . ? C3 C4 C5 C6 0.3(5) . . . . ? C40 C4 C5 C6 -179.9(3) . . . . ? C4 C5 C6 C1 0.0(5) . . . . ? C2 C1 C6 C5 -0.5(4) . . . . ? S1 C1 C6 C5 -179.6(2) . . . . ? C2 C1 S1 O1 3.7(2) . . . . ? C6 C1 S1 O1 -177.2(2) . . . . ? C2 C1 S1 O2 134.28(19) . . . . ? C6 C1 S1 O2 -46.6(2) . . . . ? C2 C1 S1 N1 -112.3(2) . . . . ? C6 C1 S1 N1 66.8(2) . . . . ? O1 S1 N1 C7 -53.45(19) . . . . ? O2 S1 N1 C7 177.64(16) . . . . ? C1 S1 N1 C7 62.13(18) . . . . ? S1 N1 C7 C8 -135.79(16) . . . . ? N1 C7 C8 C9 107.5(2) . . . . ? N1 C7 C8 C13 -71.7(2) . . . . ? C13 C8 C9 C10 -1.9(4) . . . . ? C7 C8 C9 C10 178.9(2) . . . . ? C8 C9 C10 C11 0.4(5) . . . . ? C9 C10 C11 C12 0.3(5) . . . . ? C10 C11 C12 C13 0.5(4) . . . . ? C9 C8 C13 C12 2.7(3) . . . . ? C7 C8 C13 C12 -178.1(2) . . . . ? C9 C8 C13 N2 179.2(2) . . . . ? C7 C8 C13 N2 -1.5(3) . . . . ? C11 C12 C13 C8 -2.0(4) . . . . ? C11 C12 C13 N2 -178.3(2) . . . . ? C8 C13 N2 C14 157.9(2) . . . . ? C12 C13 N2 C14 -25.7(3) . . . . ? C13 N2 C14 C15 172.5(2) . . . . ? N2 C14 C15 C16 -171.4(2) . . . . ? N2 C14 C15 C20 5.3(4) . . . . ? C20 C15 C16 C17 -1.1(4) . . . . ? C14 C15 C16 C17 175.7(3) . . . . ? C15 C16 C17 C18 1.3(5) . . . . ? C16 C17 C18 C19 -0.7(5) . . . . ? C17 C18 C19 C20 0.1(4) . . . . ? C18 C19 C20 N3 -178.8(2) . . . . ? C18 C19 C20 C15 0.0(4) . . . . ? C16 C15 C20 C19 0.5(3) . . . . ? C14 C15 C20 C19 -176.1(2) . . . . ? C16 C15 C20 N3 179.4(2) . . . . ? C14 C15 C20 N3 2.8(3) . . . . ? C19 C20 N3 S2 -10.4(3) . . . . ? C15 C20 N3 S2 170.69(18) . . . . ? C20 N3 S2 O3 178.2(2) . . . . ? C20 N3 S2 O4 48.5(2) . . . . ? C20 N3 S2 C21 -67.2(2) . . . . ? O3 S2 C21 C26 -145.46(17) . . . . ? O4 S2 C21 C26 -14.3(2) . . . . ? N3 S2 C21 C26 103.02(17) . . . . ? O3 S2 C21 C22 34.6(2) . . . . ? O4 S2 C21 C22 165.75(17) . . . . ? N3 S2 C21 C22 -76.92(19) . . . . ? C26 C21 C22 C23 0.1(3) . . . . ? S2 C21 C22 C23 -179.93(19) . . . . ? C21 C22 C23 C24 -0.8(4) . . . . ? C22 C23 C24 C25 0.4(4) . . . . ? C22 C23 C24 C240 -179.1(3) . . . . ? C23 C24 C25 C26 0.6(4) . . . . ? C240 C24 C25 C26 -179.8(3) . . . . ? C24 C25 C26 C21 -1.3(3) . . . . ? C22 C21 C26 C25 0.9(3) . . . . ? S2 C21 C26 C25 -179.04(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O2 0.99 1.99 2.977(2) 175.2 2_676 N3 H3 N2 0.92 1.91 2.665(2) 137.6 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 73.45 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.470 _refine_diff_density_min -0.811 _refine_diff_density_rms 0.069