# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Ms Elisa Nauha' _publ_contact_author_email maija.nissinen@jyu.fi _publ_section_title ; Comparison of the polymorphs and solvates of two analogous fungicides - a case study of the applicability of a supramolecular synthon approach in crystal engineering ; loop_ _publ_author_name E.Nauha A.Ojala M.Nissinen H.Saxell # Attachment '- TE_structures2.cif' data_TE-formI _database_code_depnum_ccdc_archive 'CCDC 770744' #TrackingRef '- TE_structures2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common thiophanate-ethyl _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 N4 O4 S2' _chemical_formula_sum 'C14 H18 N4 O4 S2' _chemical_formula_weight 370.44 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_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.99110(10) _cell_length_b 9.6750(2) _cell_length_c 12.5109(3) _cell_angle_alpha 69.055(3) _cell_angle_beta 81.270(3) _cell_angle_gamma 73.033(3) _cell_volume 862.81(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 3.041 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5815 _exptl_absorpt_correction_T_max 0.7508 _exptl_absorpt_process_details ; Denzo (Otwinowski, Borek, Majewski & Minor,2003) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4039 _diffrn_reflns_av_R_equivalents 0.0848 _diffrn_reflns_av_sigmaI/netI 0.0521 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.79 _diffrn_reflns_theta_max 66.79 _reflns_number_total 2936 _reflns_number_gt 2575 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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. The N-H hydrogen atoms found in the electron density map were restrained to a distance of 0.91 \%A to give the best fit to the X-ray data and to ensure stable refinement ; _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^)+(0.0792P)^2^+0.4194P] 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 0.0066(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2936 _refine_ls_number_parameters 232 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1299 _refine_ls_wR_factor_gt 0.1235 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.00043(8) 0.85421(6) 0.18110(5) 0.0304(2) Uani 1 1 d . . . S2 S 0.42745(7) 0.53130(7) 0.23794(5) 0.0330(2) Uani 1 1 d . . . O1 O -0.3752(2) 0.7562(2) -0.00915(16) 0.0367(4) Uani 1 1 d . . . O2 O -0.3159(3) 0.9674(2) -0.14361(16) 0.0389(5) Uani 1 1 d . . . O3 O 0.0826(2) 0.6271(2) -0.05401(16) 0.0374(4) Uani 1 1 d . . . O4 O 0.2781(2) 0.75754(18) -0.15617(14) 0.0292(4) Uani 1 1 d . . . N1 N -0.2115(3) 0.8948(2) 0.02512(19) 0.0309(5) Uani 1 1 d D . . H1N H -0.158(3) 0.967(3) -0.009(2) 0.037 Uiso 1 1 d D . . N2 N -0.2012(2) 0.6755(2) 0.18383(18) 0.0270(4) Uani 1 1 d D . . H2N H -0.280(3) 0.662(3) 0.148(2) 0.032 Uiso 1 1 d D . . N3 N 0.1413(2) 0.5030(2) 0.16795(17) 0.0263(4) Uani 1 1 d D . . H3N H 0.085(3) 0.531(3) 0.1035(18) 0.032 Uiso 1 1 d D . . N4 N 0.3251(3) 0.6225(2) 0.02731(18) 0.0281(5) Uani 1 1 d D . . H4N H 0.419(3) 0.660(3) 0.010(2) 0.034 Uiso 1 1 d D . . C1 C -0.3813(5) 1.0718(4) -0.3370(3) 0.0590(9) Uani 1 1 d . . . H1A H -0.4045 1.1722 -0.3276 0.088 Uiso 1 1 calc R . . H1B H -0.4567 1.0787 -0.3946 0.088 Uiso 1 1 calc R . . H1C H -0.2582 1.0399 -0.3622 0.088 Uiso 1 1 calc R . . C2 C -0.4184(4) 0.9572(3) -0.2254(2) 0.0402(6) Uani 1 1 d . . . H2A H -0.5448 0.9818 -0.2024 0.048 Uiso 1 1 calc R . . H2B H -0.3829 0.8529 -0.2308 0.048 Uiso 1 1 calc R . . C3 C -0.3079(3) 0.8628(3) -0.0407(2) 0.0292(5) Uani 1 1 d . . . C4 C -0.1441(3) 0.8018(2) 0.1303(2) 0.0261(5) Uani 1 1 d . . . C5 C -0.1247(3) 0.5569(2) 0.2840(2) 0.0251(5) Uani 1 1 d . . . C6 C -0.2250(3) 0.5225(3) 0.3863(2) 0.0307(5) Uani 1 1 d . . . H6 H -0.3427 0.5807 0.3907 0.037 Uiso 1 1 calc R . . C7 C -0.1538(4) 0.4036(3) 0.4818(2) 0.0347(6) Uani 1 1 d . . . H7 H -0.2223 0.3807 0.5518 0.042 Uiso 1 1 calc R . . C8 C 0.0173(4) 0.3179(3) 0.4751(2) 0.0358(6) Uani 1 1 d . . . H8 H 0.0658 0.2363 0.5407 0.043 Uiso 1 1 calc R . . C9 C 0.1191(3) 0.3507(3) 0.3725(2) 0.0315(6) Uani 1 1 d . . . H9 H 0.2366 0.2917 0.3687 0.038 Uiso 1 1 calc R . . C10 C 0.0485(3) 0.4694(2) 0.2763(2) 0.0256(5) Uani 1 1 d . . . C11 C 0.2886(3) 0.5514(2) 0.1429(2) 0.0259(5) Uani 1 1 d . . . C12 C 0.2166(3) 0.6664(2) -0.0613(2) 0.0274(5) Uani 1 1 d . . . C13 C 0.1784(3) 0.7993(3) -0.2569(2) 0.0334(6) Uani 1 1 d . . . H13A H 0.0579 0.8597 -0.2454 0.040 Uiso 1 1 calc R . . H13B H 0.1714 0.7059 -0.2696 0.040 Uiso 1 1 calc R . . C14 C 0.2699(4) 0.8918(3) -0.3577(2) 0.0440(7) Uani 1 1 d . . . H14A H 0.2731 0.9854 -0.3453 0.066 Uiso 1 1 calc R . . H14B H 0.2069 0.9190 -0.4267 0.066 Uiso 1 1 calc R . . H14C H 0.3898 0.8319 -0.3674 0.066 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 S1 0.0372(4) 0.0234(3) 0.0334(4) -0.0065(3) -0.0065(3) -0.0132(2) S2 0.0274(3) 0.0396(4) 0.0316(4) -0.0074(3) -0.0041(2) -0.0125(3) O1 0.0383(10) 0.0399(10) 0.0333(10) -0.0017(8) -0.0058(8) -0.0234(8) O2 0.0507(11) 0.0345(9) 0.0309(10) 0.0026(8) -0.0116(8) -0.0222(8) O3 0.0396(10) 0.0452(10) 0.0331(10) -0.0069(8) -0.0043(8) -0.0255(8) O4 0.0336(9) 0.0272(8) 0.0270(9) -0.0054(7) -0.0020(7) -0.0124(7) N1 0.0372(11) 0.0231(10) 0.0316(12) -0.0024(9) -0.0060(9) -0.0130(8) N2 0.0273(10) 0.0260(10) 0.0286(11) -0.0047(9) -0.0050(8) -0.0119(8) N3 0.0285(10) 0.0268(10) 0.0253(11) -0.0062(8) -0.0002(8) -0.0135(8) N4 0.0255(10) 0.0285(10) 0.0312(11) -0.0073(9) 0.0012(8) -0.0127(8) C1 0.068(2) 0.073(2) 0.0346(17) 0.0028(16) -0.0106(15) -0.0382(18) C2 0.0459(15) 0.0434(15) 0.0321(15) -0.0054(12) -0.0079(12) -0.0186(12) C3 0.0265(11) 0.0261(12) 0.0326(14) -0.0053(10) -0.0007(10) -0.0089(9) C4 0.0258(11) 0.0221(11) 0.0290(13) -0.0065(10) -0.0010(9) -0.0069(9) C5 0.0300(11) 0.0213(10) 0.0264(12) -0.0050(9) -0.0026(9) -0.0129(9) C6 0.0332(12) 0.0323(12) 0.0305(14) -0.0102(11) 0.0031(10) -0.0166(10) C7 0.0470(15) 0.0349(13) 0.0262(13) -0.0070(11) 0.0043(11) -0.0237(11) C8 0.0499(15) 0.0263(12) 0.0299(14) -0.0002(10) -0.0071(11) -0.0166(11) C9 0.0360(13) 0.0258(12) 0.0320(14) -0.0059(10) -0.0063(10) -0.0093(10) C10 0.0299(12) 0.0218(11) 0.0285(13) -0.0057(10) -0.0022(9) -0.0148(9) C11 0.0247(11) 0.0199(10) 0.0323(13) -0.0092(10) 0.0002(9) -0.0044(9) C12 0.0304(12) 0.0215(11) 0.0313(13) -0.0103(10) 0.0010(10) -0.0077(9) C13 0.0409(14) 0.0302(12) 0.0313(14) -0.0070(11) -0.0083(11) -0.0130(10) C14 0.0518(16) 0.0454(15) 0.0315(15) -0.0030(12) -0.0048(12) -0.0189(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 C4 1.671(2) . ? S2 C11 1.671(2) . ? O1 C3 1.215(3) . ? O2 C3 1.320(3) . ? O2 C2 1.449(3) . ? O3 C12 1.217(3) . ? O4 C12 1.325(3) . ? O4 C13 1.462(3) . ? N1 C3 1.372(3) . ? N1 C4 1.385(3) . ? N1 H1N 0.870(17) . ? N2 C4 1.340(3) . ? N2 C5 1.434(3) . ? N2 H2N 0.893(17) . ? N3 C11 1.344(3) . ? N3 C10 1.419(3) . ? N3 H3N 0.902(17) . ? N4 C12 1.379(3) . ? N4 C11 1.388(3) . ? N4 H4N 0.887(17) . ? C1 C2 1.493(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C5 C6 1.390(3) . ? C5 C10 1.405(3) . ? C6 C7 1.384(4) . ? C6 H6 0.9500 . ? C7 C8 1.384(4) . ? C7 H7 0.9500 . ? C8 C9 1.397(4) . ? C8 H8 0.9500 . ? C9 C10 1.388(3) . ? C9 H9 0.9500 . ? C13 C14 1.490(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 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 C3 O2 C2 117.2(2) . . ? C12 O4 C13 114.23(18) . . ? C3 N1 C4 127.9(2) . . ? C3 N1 H1N 118(2) . . ? C4 N1 H1N 112(2) . . ? C4 N2 C5 123.13(19) . . ? C4 N2 H2N 115.7(18) . . ? C5 N2 H2N 120.6(18) . . ? C11 N3 C10 126.0(2) . . ? C11 N3 H3N 109.8(18) . . ? C10 N3 H3N 119.9(18) . . ? C12 N4 C11 127.0(2) . . ? C12 N4 H4N 115.8(19) . . ? C11 N4 H4N 116.0(19) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 C1 105.4(2) . . ? O2 C2 H2A 110.7 . . ? C1 C2 H2A 110.7 . . ? O2 C2 H2B 110.7 . . ? C1 C2 H2B 110.7 . . ? H2A C2 H2B 108.8 . . ? O1 C3 O2 125.8(2) . . ? O1 C3 N1 125.6(2) . . ? O2 C3 N1 108.6(2) . . ? N2 C4 N1 116.8(2) . . ? N2 C4 S1 124.96(19) . . ? N1 C4 S1 118.22(17) . . ? C6 C5 C10 120.2(2) . . ? C6 C5 N2 120.0(2) . . ? C10 C5 N2 119.7(2) . . ? C7 C6 C5 120.1(2) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 120.0(2) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C7 C8 C9 120.4(2) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C10 C9 C8 120.0(2) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C5 119.3(2) . . ? C9 C10 N3 122.8(2) . . ? C5 C10 N3 117.9(2) . . ? N3 C11 N4 115.5(2) . . ? N3 C11 S2 125.60(19) . . ? N4 C11 S2 118.90(17) . . ? O3 C12 O4 124.3(2) . . ? O3 C12 N4 125.0(2) . . ? O4 C12 N4 110.7(2) . . ? O4 C13 C14 108.1(2) . . ? O4 C13 H13A 110.1 . . ? C14 C13 H13A 110.1 . . ? O4 C13 H13B 110.1 . . ? C14 C13 H13B 110.1 . . ? H13A C13 H13B 108.4 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 C3 O2 C2 C1 -171.3(2) . . . . ? C2 O2 C3 O1 2.0(4) . . . . ? C2 O2 C3 N1 -177.7(2) . . . . ? C4 N1 C3 O1 12.8(4) . . . . ? C4 N1 C3 O2 -167.5(2) . . . . ? C5 N2 C4 N1 170.2(2) . . . . ? C5 N2 C4 S1 -9.9(3) . . . . ? C3 N1 C4 N2 -11.6(4) . . . . ? C3 N1 C4 S1 168.55(19) . . . . ? C4 N2 C5 C6 118.4(2) . . . . ? C4 N2 C5 C10 -65.6(3) . . . . ? C10 C5 C6 C7 1.2(3) . . . . ? N2 C5 C6 C7 177.1(2) . . . . ? C5 C6 C7 C8 -0.5(4) . . . . ? C6 C7 C8 C9 0.1(4) . . . . ? C7 C8 C9 C10 -0.3(4) . . . . ? C8 C9 C10 C5 0.9(3) . . . . ? C8 C9 C10 N3 -176.3(2) . . . . ? C6 C5 C10 C9 -1.4(3) . . . . ? N2 C5 C10 C9 -177.3(2) . . . . ? C6 C5 C10 N3 176.0(2) . . . . ? N2 C5 C10 N3 0.0(3) . . . . ? C11 N3 C10 C9 -64.7(3) . . . . ? C11 N3 C10 C5 118.1(2) . . . . ? C10 N3 C11 N4 -160.3(2) . . . . ? C10 N3 C11 S2 20.3(3) . . . . ? C12 N4 C11 N3 9.4(3) . . . . ? C12 N4 C11 S2 -171.16(18) . . . . ? C13 O4 C12 O3 -4.7(3) . . . . ? C13 O4 C12 N4 175.21(18) . . . . ? C11 N4 C12 O3 -12.7(4) . . . . ? C11 N4 C12 O4 167.41(19) . . . . ? C12 O4 C13 C14 -176.0(2) . . . . ? 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 H1N S1 0.870(17) 2.65(2) 3.462(2) 156(3) 2_575 N2 H2N O1 0.893(17) 2.01(2) 2.722(3) 136(2) . N2 H2N S2 0.893(17) 2.87(2) 3.513(2) 130(2) 1_455 N3 H3N O3 0.902(17) 1.85(2) 2.656(3) 147(3) . N3 H3N O3 0.902(17) 2.57(2) 3.192(3) 126(2) 2_565 N4 H4N O1 0.887(17) 2.064(18) 2.945(3) 172(3) 1_655 _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 66.79 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.398 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.067 data_TE-formII _database_code_depnum_ccdc_archive 'CCDC 770745' #TrackingRef '- TE_structures2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common thiphanate-ethyl _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 N4 O4 S2' _chemical_formula_sum 'C14 H18 N4 O4 S2' _chemical_formula_weight 370.44 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 p2(1)/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 4.72710(10) _cell_length_b 16.0239(3) _cell_length_c 22.6450(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.750(3) _cell_angle_gamma 90.00 _cell_volume 1711.61(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 3.066 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7491 _exptl_absorpt_correction_T_max 0.7491 _exptl_absorpt_process_details ; Denzo (Otwinowski, Borek, Majewski & Minor,2003) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4691 _diffrn_reflns_av_R_equivalents 0.0616 _diffrn_reflns_av_sigmaI/netI 0.0715 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 66.65 _reflns_number_total 2931 _reflns_number_gt 2074 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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. The N-H hydrogen atoms found in the electron density map were restrained to a distance of 0.91 \%A to give the best fit to the X-ray data and to ensure stable refinement ; _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^)+(0.0427P)^2^+1.4457P] 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 2931 _refine_ls_number_parameters 231 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0898 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.1283 _refine_ls_wR_factor_gt 0.1120 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 -0.3843(2) 0.55043(6) 0.08720(4) 0.0409(3) Uani 1 1 d . . . S2 S -0.0263(2) 0.92559(5) 0.07849(4) 0.0342(3) Uani 1 1 d . . . O1 O 0.1153(6) 0.68567(15) -0.05070(11) 0.0400(6) Uani 1 1 d . . . O2 O -0.1722(6) 0.60723(15) -0.11197(11) 0.0416(7) Uani 1 1 d . . . O3 O 0.6272(6) 0.80769(15) -0.03744(11) 0.0383(6) Uani 1 1 d . . . O4 O 0.4674(6) 0.91080(15) -0.09934(11) 0.0401(6) Uani 1 1 d . . . N1 N -0.2290(7) 0.60008(18) -0.01593(13) 0.0361(7) Uani 1 1 d D . . H1N H -0.363(6) 0.5634(19) -0.0294(17) 0.043 Uiso 1 1 d D . . N2 N -0.0324(7) 0.67655(18) 0.06149(13) 0.0348(7) Uani 1 1 d D . . H2N H 0.047(8) 0.697(2) 0.0294(12) 0.042 Uiso 1 1 d D . . N3 N 0.3430(6) 0.80401(17) 0.06172(13) 0.0312(7) Uani 1 1 d D . . H3N H 0.478(6) 0.788(2) 0.0383(14) 0.037 Uiso 1 1 d D . . N4 N 0.2914(6) 0.90364(17) -0.01212(13) 0.0311(7) Uani 1 1 d D . . H4N H 0.182(7) 0.9477(17) -0.0231(16) 0.037 Uiso 1 1 d D . . C1 C -0.1154(10) 0.5776(3) -0.21286(17) 0.0508(11) Uani 1 1 d . . . H1A H -0.0685 0.5191 -0.2042 0.076 Uiso 1 1 calc R . . H1B H -0.0238 0.5952 -0.2484 0.076 Uiso 1 1 calc R . . H1C H -0.3214 0.5835 -0.2195 0.076 Uiso 1 1 calc R . . C2 C -0.0120(9) 0.6312(2) -0.16141(16) 0.0428(10) Uani 1 1 d . . . H2A H 0.1931 0.6221 -0.1519 0.051 Uiso 1 1 calc R . . H2B H -0.0429 0.6909 -0.1709 0.051 Uiso 1 1 calc R . . C3 C -0.0769(8) 0.6362(2) -0.05906(16) 0.0354(9) Uani 1 1 d . . . C4 C -0.2022(8) 0.6125(2) 0.04492(16) 0.0327(8) Uani 1 1 d . . . C5 C 0.0822(8) 0.7024(2) 0.11788(15) 0.0303(8) Uani 1 1 d . . . C6 C 0.0156(9) 0.6699(2) 0.17185(16) 0.0371(9) Uani 1 1 d . . . H6 H -0.1238 0.6273 0.1734 0.045 Uiso 1 1 calc R . . C7 C 0.1526(8) 0.6994(2) 0.22384(16) 0.0387(9) Uani 1 1 d . . . H7 H 0.1048 0.6769 0.2607 0.046 Uiso 1 1 calc R . . C8 C 0.3569(9) 0.7609(2) 0.22302(17) 0.0410(9) Uani 1 1 d . . . H8 H 0.4517 0.7794 0.2589 0.049 Uiso 1 1 calc R . . C9 C 0.4228(9) 0.7953(2) 0.16928(16) 0.0385(9) Uani 1 1 d . . . H9 H 0.5623 0.8379 0.1682 0.046 Uiso 1 1 calc R . . C10 C 0.2829(7) 0.7671(2) 0.11709(15) 0.0308(8) Uani 1 1 d . . . C11 C 0.2174(7) 0.8745(2) 0.04227(15) 0.0293(8) Uani 1 1 d . . . C12 C 0.4804(8) 0.8677(2) -0.04834(15) 0.0320(8) Uani 1 1 d . . . C13 C 0.6589(9) 0.8838(2) -0.14318(16) 0.0439(10) Uani 1 1 d . . . H13A H 0.6123 0.8264 -0.1567 0.053 Uiso 1 1 calc R . . H13B H 0.8577 0.8849 -0.1264 0.053 Uiso 1 1 calc R . . C14 C 0.6182(10) 0.9443(2) -0.19353(17) 0.0492(11) Uani 1 1 d . . . H14A H 0.4191 0.9439 -0.2086 0.074 Uiso 1 1 calc R . . H14B H 0.7386 0.9281 -0.2252 0.074 Uiso 1 1 calc R . . H14C H 0.6704 1.0005 -0.1797 0.074 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 S1 0.0493(6) 0.0369(5) 0.0370(5) 0.0008(4) 0.0067(5) -0.0094(5) S2 0.0391(5) 0.0310(5) 0.0332(5) 0.0030(4) 0.0071(4) 0.0051(4) O1 0.0424(15) 0.0371(14) 0.0407(14) -0.0014(12) 0.0038(13) -0.0081(13) O2 0.0503(16) 0.0434(15) 0.0313(13) -0.0022(12) 0.0048(12) -0.0092(13) O3 0.0430(15) 0.0327(14) 0.0396(14) 0.0026(12) 0.0056(12) 0.0085(13) O4 0.0494(16) 0.0378(14) 0.0344(13) 0.0058(11) 0.0119(12) 0.0072(13) N1 0.0391(18) 0.0331(16) 0.0358(17) -0.0031(14) 0.0010(15) -0.0076(14) N2 0.0474(19) 0.0287(16) 0.0285(15) 0.0039(13) 0.0040(15) -0.0041(15) N3 0.0367(17) 0.0264(15) 0.0310(16) 0.0010(13) 0.0051(14) 0.0008(14) N4 0.0369(17) 0.0254(15) 0.0313(15) 0.0038(13) 0.0058(14) 0.0064(13) C1 0.070(3) 0.044(2) 0.038(2) -0.0015(19) 0.004(2) 0.003(2) C2 0.051(2) 0.044(2) 0.034(2) 0.0054(18) 0.0072(19) -0.002(2) C3 0.040(2) 0.0312(19) 0.035(2) 0.0032(17) 0.0046(18) 0.0050(19) C4 0.037(2) 0.0260(17) 0.0349(19) 0.0017(16) 0.0042(17) 0.0035(17) C5 0.036(2) 0.0226(16) 0.0327(19) -0.0003(15) 0.0027(16) 0.0074(16) C6 0.046(2) 0.0273(18) 0.038(2) 0.0022(16) 0.0047(19) -0.0013(18) C7 0.049(2) 0.037(2) 0.0297(19) 0.0073(16) 0.0030(18) 0.0035(19) C8 0.051(2) 0.037(2) 0.035(2) -0.0007(17) -0.0019(18) 0.001(2) C9 0.042(2) 0.0329(19) 0.040(2) 0.0043(17) 0.0003(19) -0.0011(18) C10 0.0331(19) 0.0260(17) 0.0333(19) 0.0028(15) 0.0019(16) 0.0047(16) C11 0.0351(19) 0.0223(17) 0.0302(18) -0.0015(14) 0.0005(16) -0.0044(16) C12 0.038(2) 0.0246(18) 0.0334(19) -0.0007(16) 0.0028(17) -0.0036(18) C13 0.053(3) 0.043(2) 0.037(2) -0.0061(18) 0.0115(19) 0.007(2) C14 0.069(3) 0.043(2) 0.037(2) -0.0021(18) 0.013(2) -0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C4 1.659(4) . ? S2 C11 1.671(4) . ? O1 C3 1.212(4) . ? O2 C3 1.335(4) . ? O2 C2 1.444(4) . ? O3 C12 1.202(4) . ? O4 C12 1.344(4) . ? O4 C13 1.452(4) . ? N1 C3 1.377(5) . ? N1 C4 1.390(5) . ? N1 H1N 0.902(19) . ? N2 C4 1.342(4) . ? N2 C5 1.416(4) . ? N2 H2N 0.899(19) . ? N3 C11 1.337(4) . ? N3 C10 1.432(4) . ? N3 H3N 0.892(18) . ? N4 C12 1.378(5) . ? N4 C11 1.383(4) . ? N4 H4N 0.899(18) . ? C1 C2 1.504(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C5 C6 1.384(5) . ? C5 C10 1.406(5) . ? C6 C7 1.390(5) . ? C6 H6 0.9500 . ? C7 C8 1.380(5) . ? C7 H7 0.9500 . ? C8 C9 1.390(5) . ? C8 H8 0.9500 . ? C9 C10 1.392(5) . ? C9 H9 0.9500 . ? C13 C14 1.499(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 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 C3 O2 C2 116.1(3) . . ? C12 O4 C13 116.1(3) . . ? C3 N1 C4 128.7(3) . . ? C3 N1 H1N 115(3) . . ? C4 N1 H1N 116(3) . . ? C4 N2 C5 131.5(3) . . ? C4 N2 H2N 109(2) . . ? C5 N2 H2N 118(3) . . ? C11 N3 C10 121.9(3) . . ? C11 N3 H3N 112(2) . . ? C10 N3 H3N 126(2) . . ? C12 N4 C11 126.9(3) . . ? C12 N4 H4N 123(2) . . ? C11 N4 H4N 110(2) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 C1 106.8(3) . . ? O2 C2 H2A 110.4 . . ? C1 C2 H2A 110.4 . . ? O2 C2 H2B 110.4 . . ? C1 C2 H2B 110.4 . . ? H2A C2 H2B 108.6 . . ? O1 C3 O2 125.0(3) . . ? O1 C3 N1 125.8(4) . . ? O2 C3 N1 109.2(3) . . ? N2 C4 N1 113.6(3) . . ? N2 C4 S1 128.4(3) . . ? N1 C4 S1 118.0(3) . . ? C6 C5 C10 118.8(3) . . ? C6 C5 N2 126.2(3) . . ? C10 C5 N2 115.0(3) . . ? C5 C6 C7 120.0(4) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 121.3(3) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 C9 119.5(4) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C8 C9 C10 119.5(4) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C9 C10 C5 120.8(3) . . ? C9 C10 N3 119.9(3) . . ? C5 C10 N3 119.3(3) . . ? N3 C11 N4 116.4(3) . . ? N3 C11 S2 123.9(3) . . ? N4 C11 S2 119.6(2) . . ? O3 C12 O4 125.5(3) . . ? O3 C12 N4 126.9(3) . . ? O4 C12 N4 107.5(3) . . ? O4 C13 C14 105.8(3) . . ? O4 C13 H13A 110.6 . . ? C14 C13 H13A 110.6 . . ? O4 C13 H13B 110.6 . . ? C14 C13 H13B 110.6 . . ? H13A C13 H13B 108.7 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 C3 O2 C2 C1 167.8(3) . . . . ? C2 O2 C3 O1 6.6(5) . . . . ? C2 O2 C3 N1 -172.7(3) . . . . ? C4 N1 C3 O1 1.1(6) . . . . ? C4 N1 C3 O2 -179.6(3) . . . . ? C5 N2 C4 N1 -169.7(3) . . . . ? C5 N2 C4 S1 12.2(6) . . . . ? C3 N1 C4 N2 10.1(5) . . . . ? C3 N1 C4 S1 -171.6(3) . . . . ? C4 N2 C5 C6 -7.6(6) . . . . ? C4 N2 C5 C10 172.1(4) . . . . ? C10 C5 C6 C7 -2.0(5) . . . . ? N2 C5 C6 C7 177.7(3) . . . . ? C5 C6 C7 C8 -0.3(6) . . . . ? C6 C7 C8 C9 1.5(6) . . . . ? C7 C8 C9 C10 -0.3(6) . . . . ? C8 C9 C10 C5 -2.0(5) . . . . ? C8 C9 C10 N3 178.1(3) . . . . ? C6 C5 C10 C9 3.1(5) . . . . ? N2 C5 C10 C9 -176.6(3) . . . . ? C6 C5 C10 N3 -176.9(3) . . . . ? N2 C5 C10 N3 3.4(5) . . . . ? C11 N3 C10 C9 -83.5(4) . . . . ? C11 N3 C10 C5 96.5(4) . . . . ? C10 N3 C11 N4 -179.5(3) . . . . ? C10 N3 C11 S2 -1.7(5) . . . . ? C12 N4 C11 N3 0.1(5) . . . . ? C12 N4 C11 S2 -177.8(3) . . . . ? C13 O4 C12 O3 -3.1(5) . . . . ? C13 O4 C12 N4 178.3(3) . . . . ? C11 N4 C12 O3 -5.1(6) . . . . ? C11 N4 C12 O4 173.6(3) . . . . ? C12 O4 C13 C14 -176.3(3) . . . . ? 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 H1N S1 0.902(19) 2.50(2) 3.373(3) 162(3) 3_465 N2 H2N O1 0.899(19) 1.87(3) 2.682(4) 149(3) . N3 H3N O3 0.892(18) 1.92(3) 2.692(4) 143(3) . N4 H4N S2 0.899(18) 2.47(2) 3.327(3) 159(3) 3_575 _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 66.65 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.239 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.064 data_TE-acetone _database_code_depnum_ccdc_archive 'CCDC 770746' #TrackingRef '- TE_structures2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 N4 O4 S2, C3 H6 O' _chemical_formula_sum 'C17 H24 N4 O5 S2' _chemical_formula_weight 428.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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 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 16.0607(2) _cell_length_b 17.4629(2) _cell_length_c 8.45600(10) _cell_angle_alpha 90.00 _cell_angle_beta 111.432(3) _cell_angle_gamma 90.00 _cell_volume 2207.63(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 2.482 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5758 _exptl_absorpt_correction_T_max 0.6367 _exptl_absorpt_process_details ; Denzo (Otwinowski, Borek, Majewski & Minor,2003) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2547 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.89 _diffrn_reflns_theta_max 66.58 _reflns_number_total 1878 _reflns_number_gt 1719 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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. The N-H hydrogen atoms found in the electron density map were restrained to a distance of 0.91 \%A to give the best fit to the X-ray data and to ensure stable refinement ; _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^)+(0.0464P)^2^+1.9628P] 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 1878 _refine_ls_number_parameters 136 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0393 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0936 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.18336(3) 0.35391(3) 0.50617(6) 0.0478(2) Uani 1 1 d . . . O1 O 0.18311(9) 0.17643(7) 0.06860(16) 0.0420(3) Uani 1 1 d . . . O2 O 0.07716(10) 0.26643(7) -0.04231(16) 0.0493(4) Uani 1 1 d . . . N1 N 0.16550(10) 0.26461(8) 0.24240(18) 0.0348(3) Uani 1 1 d D . . H1N H 0.2088(12) 0.2376(11) 0.321(2) 0.042 Uiso 1 1 d D . . N2 N 0.07077(9) 0.36904(8) 0.18696(18) 0.0315(3) Uani 1 1 d D . . H2N H 0.0506(13) 0.3533(10) 0.081(2) 0.038 Uiso 1 1 d D . . C1 C 0.22095(16) 0.07601(13) -0.0822(3) 0.0597(6) Uani 1 1 d . . . H1A H 0.2831 0.0938 -0.0342 0.090 Uiso 1 1 calc R . . H1B H 0.2095 0.0530 -0.1940 0.090 Uiso 1 1 calc R . . H1C H 0.2107 0.0377 -0.0065 0.090 Uiso 1 1 calc R . . C2 C 0.15911(14) 0.14247(11) -0.1006(2) 0.0470(5) Uani 1 1 d . . . H2A H 0.1664 0.1804 -0.1815 0.056 Uiso 1 1 calc R . . H2B H 0.0961 0.1249 -0.1430 0.056 Uiso 1 1 calc R . . C3 C 0.13598(12) 0.23815(9) 0.0768(2) 0.0350(4) Uani 1 1 d . . . C4 C 0.13613(11) 0.32933(9) 0.3010(2) 0.0311(4) Uani 1 1 d . . . C5 C 0.03634(11) 0.43970(9) 0.22428(19) 0.0278(3) Uani 1 1 d . . . C6 C 0.07336(11) 0.50857(9) 0.2000(2) 0.0302(4) Uani 1 1 d . . . H6 H 0.1235 0.5086 0.1657 0.036 Uiso 1 1 calc R . . C7 C 0.03687(11) 0.57736(9) 0.2259(2) 0.0306(4) Uani 1 1 d . . . H7 H 0.0625 0.6245 0.2106 0.037 Uiso 1 1 calc R . . O100 O 0.0000 -0.00252(17) 0.2500 0.1048(11) Uani 1 2 d S . . C100 C 0.0000 0.0667(2) 0.2500 0.0631(9) Uani 1 2 d S . . C101 C 0.0474(2) 0.11049(19) 0.4098(4) 0.0871(9) Uani 1 1 d . . . H10A H 0.0458 0.0812 0.5075 0.131 Uiso 1 1 calc R . . H10B H 0.0177 0.1599 0.4050 0.131 Uiso 1 1 calc R . . H10C H 0.1097 0.1190 0.4217 0.131 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 S1 0.0557(3) 0.0475(3) 0.0286(3) -0.00599(19) 0.0017(2) 0.0261(2) O1 0.0472(7) 0.0368(7) 0.0344(7) -0.0085(5) 0.0058(6) 0.0129(6) O2 0.0612(9) 0.0399(7) 0.0324(7) -0.0049(6) 0.0001(6) 0.0186(6) N1 0.0400(8) 0.0301(7) 0.0290(8) 0.0000(6) 0.0062(6) 0.0118(6) N2 0.0365(8) 0.0256(7) 0.0274(7) -0.0011(6) 0.0057(6) 0.0056(6) C1 0.0595(14) 0.0564(13) 0.0553(13) -0.0214(10) 0.0116(11) 0.0155(10) C2 0.0512(12) 0.0477(11) 0.0357(10) -0.0145(8) 0.0082(9) 0.0094(9) C3 0.0402(10) 0.0276(8) 0.0336(9) -0.0019(7) 0.0094(8) 0.0050(7) C4 0.0315(9) 0.0278(8) 0.0331(9) 0.0011(7) 0.0105(7) 0.0036(7) C5 0.0290(8) 0.0237(8) 0.0249(8) 0.0005(6) 0.0030(6) 0.0030(6) C6 0.0287(8) 0.0305(8) 0.0289(8) 0.0015(6) 0.0076(7) -0.0003(6) C7 0.0344(9) 0.0234(8) 0.0287(8) 0.0007(6) 0.0054(7) -0.0031(6) O100 0.122(3) 0.0617(18) 0.111(3) 0.000 0.019(2) 0.000 C100 0.0537(19) 0.057(2) 0.081(2) 0.000 0.0276(18) 0.000 C101 0.088(2) 0.0819(19) 0.090(2) -0.0118(16) 0.0311(18) -0.0069(16) _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 C4 1.6753(17) . ? O1 C3 1.333(2) . ? O1 C2 1.464(2) . ? O2 C3 1.207(2) . ? N1 C3 1.383(2) . ? N1 C4 1.384(2) . ? N1 H1N 0.899(15) . ? N2 C4 1.332(2) . ? N2 C5 1.434(2) . ? N2 H2N 0.875(15) . ? C1 C2 1.498(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C5 C5 1.387(3) 2 ? C5 C6 1.390(2) . ? C6 C7 1.389(2) . ? C6 H6 0.9500 . ? C7 C7 1.386(3) 2 ? C7 H7 0.9500 . ? O100 C100 1.210(4) . ? C100 C101 1.496(3) 2 ? C100 C101 1.496(3) . ? C101 H10A 0.9800 . ? C101 H10B 0.9800 . ? C101 H10C 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 C3 O1 C2 115.25(13) . . ? C3 N1 C4 126.85(14) . . ? C3 N1 H1N 117.3(13) . . ? C4 N1 H1N 115.9(13) . . ? C4 N2 C5 123.65(14) . . ? C4 N2 H2N 118.4(13) . . ? C5 N2 H2N 117.8(13) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C1 106.54(16) . . ? O1 C2 H2A 110.4 . . ? C1 C2 H2A 110.4 . . ? O1 C2 H2B 110.4 . . ? C1 C2 H2B 110.4 . . ? H2A C2 H2B 108.6 . . ? O2 C3 O1 125.00(16) . . ? O2 C3 N1 125.63(15) . . ? O1 C3 N1 109.37(14) . . ? N2 C4 N1 116.56(15) . . ? N2 C4 S1 123.74(13) . . ? N1 C4 S1 119.70(12) . . ? C5 C5 C6 120.07(9) 2 . ? C5 C5 N2 120.37(9) 2 . ? C6 C5 N2 119.47(14) . . ? C7 C6 C5 119.81(15) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C7 C7 C6 120.11(10) 2 . ? C7 C7 H7 119.9 2 . ? C6 C7 H7 119.9 . . ? O100 C100 C101 120.70(18) . 2 ? O100 C100 C101 120.70(18) . . ? C101 C100 C101 118.6(4) 2 . ? C100 C101 H10A 109.5 . . ? C100 C101 H10B 109.5 . . ? H10A C101 H10B 109.5 . . ? C100 C101 H10C 109.5 . . ? H10A C101 H10C 109.5 . . ? H10B C101 H10C 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 C3 O1 C2 C1 178.56(17) . . . . ? C2 O1 C3 O2 0.0(3) . . . . ? C2 O1 C3 N1 -179.67(16) . . . . ? C4 N1 C3 O2 -2.7(3) . . . . ? C4 N1 C3 O1 176.90(16) . . . . ? C5 N2 C4 N1 -176.22(15) . . . . ? C5 N2 C4 S1 3.4(2) . . . . ? C3 N1 C4 N2 2.1(3) . . . . ? C3 N1 C4 S1 -177.53(14) . . . . ? C4 N2 C5 C5 -91.9(2) . . . 2 ? C4 N2 C5 C6 91.5(2) . . . . ? C5 C5 C6 C7 -0.6(3) 2 . . . ? N2 C5 C6 C7 176.09(14) . . . . ? C5 C6 C7 C7 -0.7(3) . . . 2 ? 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 H1N S1 0.899(15) 2.418(16) 3.3054(14) 169.4(18) 7_556 N2 H2N O2 0.875(15) 1.976(17) 2.6693(18) 135.2(17) . _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 66.58 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.208 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.040 data_TE-chloroform _database_code_depnum_ccdc_archive 'CCDC 770747' #TrackingRef '- TE_structures2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 N4 O4 S2, C H Cl3' _chemical_formula_sum 'C15 H19 Cl3 N4 O4 S2' _chemical_formula_weight 489.81 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' Cl Cl 0.3639 0.7018 '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 15.5158(3) _cell_length_b 18.0503(4) _cell_length_c 8.5922(2) _cell_angle_alpha 90.00 _cell_angle_beta 112.739(3) _cell_angle_gamma 90.00 _cell_volume 2219.34(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 5.755 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3272 _exptl_absorpt_correction_T_max 0.4240 _exptl_absorpt_process_details ; Denzo (Otwinowski, Borek, Majewski & Minor,2003) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2817 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_sigmaI/netI 0.0462 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.94 _diffrn_reflns_theta_max 66.57 _reflns_number_total 1907 _reflns_number_gt 1554 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0996P)^2^+12.3692P] 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 1907 _refine_ls_number_parameters 134 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0893 _refine_ls_R_factor_gt 0.0755 _refine_ls_wR_factor_ref 0.2058 _refine_ls_wR_factor_gt 0.1918 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.18743(8) 0.14490(6) 1.00705(14) 0.0466(4) Uani 1 1 d . . . O1 O 0.0826(3) 0.22327(17) 0.4588(4) 0.0509(9) Uani 1 1 d . . . O2 O 0.1809(2) 0.31790(16) 0.5739(4) 0.0375(7) Uani 1 1 d . . . N1 N 0.1683(2) 0.22993(18) 0.7442(4) 0.0308(8) Uani 1 1 d . . . H1N H 0.2105 0.2575 0.8206 0.037 Uiso 1 1 calc R . . N2 N 0.0729(2) 0.12729(17) 0.6877(4) 0.0302(8) Uani 1 1 d . . . H2N H 0.0493 0.1439 0.5833 0.036 Uiso 1 1 calc R . . C1 C 0.2149(4) 0.4170(3) 0.4236(7) 0.0558(14) Uani 1 1 d . . . H1A H 0.1990 0.4546 0.4904 0.084 Uiso 1 1 calc R . . H1B H 0.2037 0.4369 0.3113 0.084 Uiso 1 1 calc R . . H1C H 0.2810 0.4035 0.4802 0.084 Uiso 1 1 calc R . . C2 C 0.1555(3) 0.3497(3) 0.4065(6) 0.0424(11) Uani 1 1 d . . . H2A H 0.0886 0.3635 0.3592 0.051 Uiso 1 1 calc R . . H2B H 0.1665 0.3134 0.3299 0.051 Uiso 1 1 calc R . . C3 C 0.1381(3) 0.2542(2) 0.5799(5) 0.0331(9) Uani 1 1 d . . . C4 C 0.1394(3) 0.1668(2) 0.8025(5) 0.0279(9) Uani 1 1 d . . . C5 C 0.0374(3) 0.0589(2) 0.7246(5) 0.0261(8) Uani 1 1 d . . . C6 C 0.0746(3) -0.0077(2) 0.6990(5) 0.0285(9) Uani 1 1 d . . . H6 H 0.1263 -0.0081 0.6656 0.034 Uiso 1 1 calc R . . C7 C 0.03552(15) -0.07387(12) 0.7227(3) 0.0272(8) Uani 1 1 d . . . H7 H 0.0589 -0.1196 0.7004 0.033 Uiso 1 1 calc R . . Cl1 Cl -0.05511(15) 0.32831(12) 0.5454(3) 0.0768(10) Uani 0.50 1 d PR A -1 Cl2 Cl -0.00692(15) 0.47407(12) 0.6024(3) 0.159(3) Uani 0.50 1 d PR A -1 Cl3 Cl 0.02866(15) 0.36611(12) 0.8749(3) 0.124(2) Uani 0.50 1 d PR A -1 C10 C -0.05103(15) 0.39411(12) 0.6606(3) 0.131(11) Uani 0.50 1 d PR A -1 H10 H -0.1147 0.4042 0.6591 0.157 Uiso 0.50 1 calc PR B -1 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 0.0507(7) 0.0413(7) 0.0323(6) 0.0090(5) -0.0009(5) -0.0251(5) O1 0.077(2) 0.0359(18) 0.0283(16) -0.0006(13) 0.0076(16) -0.0220(16) O2 0.0447(17) 0.0301(15) 0.0332(16) 0.0063(12) 0.0101(13) -0.0115(13) N1 0.0341(18) 0.0259(17) 0.0279(17) 0.0004(13) 0.0069(14) -0.0092(13) N2 0.0393(19) 0.0193(16) 0.0266(16) 0.0013(13) 0.0069(14) -0.0061(13) C1 0.060(3) 0.048(3) 0.052(3) 0.018(2) 0.013(3) -0.017(2) C2 0.048(3) 0.038(2) 0.038(2) 0.0139(19) 0.013(2) -0.003(2) C3 0.043(2) 0.0217(19) 0.035(2) 0.0012(17) 0.0159(19) -0.0056(17) C4 0.028(2) 0.0207(18) 0.034(2) 0.0012(15) 0.0103(17) -0.0019(15) C5 0.0305(19) 0.0178(18) 0.0234(18) 0.0000(14) 0.0032(15) -0.0026(15) C6 0.0279(19) 0.025(2) 0.030(2) -0.0010(15) 0.0087(17) 0.0020(15) C7 0.034(2) 0.0136(17) 0.0283(19) -0.0026(14) 0.0061(16) 0.0019(14) Cl1 0.063(2) 0.098(3) 0.077(2) 0.0183(19) 0.0355(18) 0.0147(18) Cl2 0.130(4) 0.060(2) 0.296(9) 0.047(4) 0.091(5) 0.006(2) Cl3 0.090(3) 0.148(6) 0.103(4) -0.023(3) 0.004(3) 0.007(4) C10 0.059(8) 0.079(11) 0.27(3) 0.114(16) 0.076(14) 0.032(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 C4 1.670(4) . ? O1 C3 1.201(5) . ? O2 C3 1.338(5) . ? O2 C2 1.455(5) . ? N1 C3 1.376(5) . ? N1 C4 1.387(5) . ? N1 H1N 0.8800 . ? N2 C4 1.326(5) . ? N2 C5 1.437(5) . ? N2 H2N 0.8800 . ? C1 C2 1.497(6) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C5 C5 1.387(8) 2_556 ? C5 C6 1.387(5) . ? C6 C7 1.390(4) . ? C6 H6 0.9500 . ? C7 C7 1.355(5) 2_556 ? C7 H7 0.9500 . ? Cl1 C10 1.5317 . ? Cl2 C10 1.7511 . ? Cl3 C10 1.8482 . ? C10 H10 1.0000 . ? 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 C3 O2 C2 115.4(3) . . ? C3 N1 C4 127.1(3) . . ? C3 N1 H1N 116.5 . . ? C4 N1 H1N 116.5 . . ? C4 N2 C5 123.6(3) . . ? C4 N2 H2N 118.2 . . ? C5 N2 H2N 118.2 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 C1 107.6(4) . . ? O2 C2 H2A 110.2 . . ? C1 C2 H2A 110.2 . . ? O2 C2 H2B 110.2 . . ? C1 C2 H2B 110.2 . . ? H2A C2 H2B 108.5 . . ? O1 C3 O2 124.5(4) . . ? O1 C3 N1 125.9(4) . . ? O2 C3 N1 109.7(3) . . ? N2 C4 N1 116.1(3) . . ? N2 C4 S1 123.9(3) . . ? N1 C4 S1 120.0(3) . . ? C5 C5 C6 120.0(2) 2_556 . ? C5 C5 N2 120.5(2) 2_556 . ? C6 C5 N2 119.4(4) . . ? C5 C6 C7 119.3(3) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C7 C7 C6 120.69(19) 2_556 . ? C7 C7 H7 119.7 2_556 . ? C6 C7 H7 119.7 . . ? Cl1 C10 Cl2 112.2 . . ? Cl1 C10 Cl3 106.1 . . ? Cl2 C10 Cl3 109.0 . . ? Cl1 C10 H10 109.8 . . ? Cl2 C10 H10 109.8 . . ? Cl3 C10 H10 109.8 . . ? 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 C3 O2 C2 C1 -176.0(4) . . . . ? C2 O2 C3 O1 0.5(6) . . . . ? C2 O2 C3 N1 179.7(4) . . . . ? C4 N1 C3 O1 -1.7(7) . . . . ? C4 N1 C3 O2 179.0(4) . . . . ? C5 N2 C4 N1 177.5(3) . . . . ? C5 N2 C4 S1 -3.1(6) . . . . ? C3 N1 C4 N2 -2.8(6) . . . . ? C3 N1 C4 S1 177.7(3) . . . . ? C4 N2 C5 C5 89.2(6) . . . 2_556 ? C4 N2 C5 C6 -94.8(5) . . . . ? C5 C5 C6 C7 0.8(6) 2_556 . . . ? N2 C5 C6 C7 -175.2(3) . . . . ? C5 C6 C7 C7 -2.9(5) . . . 2_556 ? 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 H1N S1 0.88 2.45 3.315(3) 168.1 7_557 N2 H2N O1 0.88 1.97 2.669(4) 134.9 . _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 66.57 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 1.067 _refine_diff_density_min -0.925 _refine_diff_density_rms 0.115 data_TE-dioxaneI _database_code_depnum_ccdc_archive 'CCDC 770748' #TrackingRef '- TE_structures2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 N4 O4 S2, C4 H8 O2' _chemical_formula_sum 'C18 H26 N4 O6 S2' _chemical_formula_weight 458.55 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 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 16.8293(3) _cell_length_b 17.0275(3) _cell_length_c 8.2545(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.119(3) _cell_angle_gamma 90.00 _cell_volume 2206.54(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 2.554 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5145 _exptl_absorpt_correction_T_max 0.6291 _exptl_absorpt_process_details ; Denzo (Otwinowski, Borek, Majewski & Minor,2003) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2410 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0389 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.83 _diffrn_reflns_theta_max 67.07 _reflns_number_total 1647 _reflns_number_gt 1443 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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. The N-H hydrogen atoms found in the electron density map were restrained to a distance of 0.91 \%A to give the best fit to the X-ray data and to ensure stable refinement The four C-O bonds on the disordered dioxane were restrained to be approximately equal (+- 0.02 \%A) with SADI to keep the model together. SADI O10A C10A O10A C40A O10B C10B O10B C40B ; _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^)+(0.0968P)^2^+7.8529P] 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 1647 _refine_ls_number_parameters 166 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0704 _refine_ls_R_factor_gt 0.0633 _refine_ls_wR_factor_ref 0.1870 _refine_ls_wR_factor_gt 0.1799 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.109 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.18040(7) 0.35254(6) 0.51093(13) 0.0440(4) Uani 1 1 d . . . O1 O 0.18713(18) 0.17573(17) 0.0643(4) 0.0418(8) Uani 1 1 d . . . O2 O 0.07865(19) 0.26012(17) -0.0445(4) 0.0465(8) Uani 1 1 d . . . N1 N 0.1664(2) 0.26302(19) 0.2426(4) 0.0338(8) Uani 1 1 d D . . H1N H 0.212(2) 0.241(3) 0.325(5) 0.051 Uiso 1 1 d D . . N2 N 0.0690(2) 0.36388(18) 0.1893(4) 0.0329(8) Uani 1 1 d D . . H2N H 0.045(3) 0.346(3) 0.083(3) 0.049 Uiso 1 1 d D . . C1 C 0.2308(3) 0.0790(3) -0.0893(7) 0.0613(14) Uani 1 1 d . . . H1A H 0.2882 0.1007 -0.0342 0.092 Uiso 1 1 calc R . . H1B H 0.2241 0.0587 -0.2046 0.092 Uiso 1 1 calc R . . H1C H 0.2223 0.0363 -0.0176 0.092 Uiso 1 1 calc R . . C2 C 0.1666(3) 0.1417(3) -0.1069(5) 0.0452(11) Uani 1 1 d . . . H2A H 0.1696 0.1821 -0.1908 0.054 Uiso 1 1 calc R . . H2B H 0.1084 0.1192 -0.1483 0.054 Uiso 1 1 calc R . . C3 C 0.1376(3) 0.2350(2) 0.0744(5) 0.0352(9) Uani 1 1 d . . . C4 C 0.1347(2) 0.3262(2) 0.3031(5) 0.0303(9) Uani 1 1 d . . . C5 C 0.0355(2) 0.4359(2) 0.2256(4) 0.0268(8) Uani 1 1 d . . . C6 C 0.0707(2) 0.5063(2) 0.2030(5) 0.0290(9) Uani 1 1 d . . . H6 H 0.1193 0.5065 0.1701 0.035 Uiso 1 1 calc R . . C7 C 0.0357(2) 0.5763(2) 0.2280(5) 0.0295(9) Uani 1 1 d . . . H7 H 0.0609 0.6247 0.2147 0.035 Uiso 1 1 calc R . . O100 O 0.0000 0.1793(4) 0.2500 0.0861(19) Uani 1 2 d SD . . C100 C 0.0688(8) 0.1303(9) 0.372(2) 0.061(4) Uani 0.50 1 d PD A -1 H10A H 0.1035 0.1611 0.4746 0.073 Uiso 0.50 1 calc PR A -1 H10B H 0.1065 0.1090 0.3138 0.073 Uiso 0.50 1 calc PR A -1 C200 C 0.0222(7) 0.0653(7) 0.4226(13) 0.064(3) Uani 0.50 1 d PD A -1 H20A H 0.0629 0.0332 0.5158 0.077 Uiso 0.50 1 calc PR A -1 H20B H -0.0203 0.0877 0.4670 0.077 Uiso 0.50 1 calc PR A -1 C300 C -0.0798(7) 0.0677(8) 0.1457(16) 0.067(3) Uani 0.50 1 d PD A -1 H30A H -0.1212 0.0893 0.1942 0.080 Uiso 0.50 1 calc PR A -1 H30B H -0.1118 0.0365 0.0412 0.080 Uiso 0.50 1 calc PR A -1 C400 C -0.0345(9) 0.1338(8) 0.0957(15) 0.051(3) Uani 0.50 1 d PD A -1 H40A H 0.0112 0.1137 0.0580 0.061 Uiso 0.50 1 calc PR A -1 H40B H -0.0747 0.1654 0.0004 0.061 Uiso 0.50 1 calc PR A -1 O200 O -0.0198(7) 0.0172(5) 0.2734(15) 0.085(3) Uani 0.50 1 d PD A -1 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 0.0481(7) 0.0462(7) 0.0274(6) -0.0071(4) 0.0012(5) 0.0213(5) O1 0.0504(17) 0.0398(17) 0.0299(15) -0.0062(12) 0.0080(13) 0.0143(13) O2 0.0550(19) 0.0409(17) 0.0302(16) -0.0043(12) -0.0008(14) 0.0167(14) N1 0.0384(18) 0.0303(18) 0.0258(17) -0.0011(13) 0.0033(14) 0.0098(13) N2 0.0335(17) 0.0294(17) 0.0276(17) -0.0042(13) 0.0013(14) 0.0045(13) C1 0.065(3) 0.067(3) 0.051(3) -0.016(2) 0.020(3) 0.019(3) C2 0.054(3) 0.050(3) 0.030(2) -0.0104(18) 0.012(2) 0.006(2) C3 0.042(2) 0.030(2) 0.032(2) -0.0020(16) 0.0096(18) 0.0017(17) C4 0.030(2) 0.030(2) 0.028(2) 0.0011(15) 0.0070(16) 0.0026(15) C5 0.0291(17) 0.0227(19) 0.0221(18) -0.0008(14) 0.0014(14) 0.0032(14) C6 0.0251(18) 0.032(2) 0.028(2) -0.0002(15) 0.0074(16) 0.0000(14) C7 0.0320(18) 0.025(2) 0.0270(19) -0.0002(14) 0.0052(15) -0.0053(14) O100 0.106(5) 0.066(4) 0.069(4) 0.000 0.010(3) 0.000 C100 0.048(8) 0.066(10) 0.059(8) 0.006(7) 0.007(6) -0.015(7) C200 0.065(7) 0.065(8) 0.057(7) 0.009(5) 0.015(5) -0.002(6) C300 0.049(6) 0.057(8) 0.079(8) -0.007(6) 0.005(6) -0.010(5) C400 0.053(8) 0.052(8) 0.036(6) -0.006(5) 0.004(6) 0.002(6) O200 0.104(10) 0.063(4) 0.092(8) -0.004(5) 0.040(6) -0.008(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 C4 1.669(4) . ? O1 C3 1.330(5) . ? O1 C2 1.449(5) . ? O2 C3 1.196(5) . ? N1 C4 1.372(5) . ? N1 C3 1.381(5) . ? N1 H1N 0.90(2) . ? N2 C4 1.329(5) . ? N2 C5 1.426(5) . ? N2 H2N 0.88(2) . ? C1 C2 1.488(7) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C5 C6 1.379(5) . ? C5 C5 1.392(7) 2 ? C6 C7 1.379(5) . ? C6 H6 0.9500 . ? C7 C7 1.375(8) 2 ? C7 H7 0.9500 . ? O100 C400 1.424(11) 2 ? O100 C400 1.424(11) . ? O100 C100 1.486(13) 2 ? O100 C100 1.486(13) . ? C100 C200 1.500(14) . ? C100 H10A 0.9900 . ? C100 H10B 0.9900 . ? C200 O200 1.436(13) . ? C200 H20A 0.9900 . ? C200 H20B 0.9900 . ? C300 O200 1.451(13) . ? C300 C400 1.499(14) . ? C300 H30A 0.9900 . ? C300 H30B 0.9900 . ? C400 H40A 0.9900 . ? C400 H40B 0.9900 . ? 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 C3 O1 C2 115.5(3) . . ? C4 N1 C3 126.5(3) . . ? C4 N1 H1N 112(3) . . ? C3 N1 H1N 121(3) . . ? C4 N2 C5 123.9(3) . . ? C4 N2 H2N 120(3) . . ? C5 N2 H2N 116(3) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C1 106.4(4) . . ? O1 C2 H2A 110.4 . . ? C1 C2 H2A 110.4 . . ? O1 C2 H2B 110.4 . . ? C1 C2 H2B 110.4 . . ? H2A C2 H2B 108.6 . . ? O2 C3 O1 125.0(4) . . ? O2 C3 N1 126.1(4) . . ? O1 C3 N1 108.9(3) . . ? N2 C4 N1 117.0(3) . . ? N2 C4 S1 123.7(3) . . ? N1 C4 S1 119.3(3) . . ? C6 C5 C5 119.6(2) . 2 ? C6 C5 N2 119.8(3) . . ? C5 C5 N2 120.5(2) 2 . ? C7 C6 C5 120.3(3) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C7 C7 C6 120.1(2) 2 . ? C7 C7 H7 120.0 2 . ? C6 C7 H7 120.0 . . ? C400 O100 C400 114.1(12) 2 . ? C400 O100 C100 105.4(7) 2 2 ? C400 O100 C100 28.6(6) . 2 ? C400 O100 C100 28.6(6) 2 . ? C400 O100 C100 105.4(7) . . ? C100 O100 C100 111.6(13) 2 . ? O100 C100 C200 104.2(10) . . ? O100 C100 H10A 110.9 . . ? C200 C100 H10A 110.9 . . ? O100 C100 H10B 110.9 . . ? C200 C100 H10B 110.9 . . ? H10A C100 H10B 108.9 . . ? O200 C200 C100 109.0(10) . . ? O200 C200 H20A 109.9 . . ? C100 C200 H20A 109.9 . . ? O200 C200 H20B 109.9 . . ? C100 C200 H20B 109.9 . . ? H20A C200 H20B 108.3 . . ? O200 C300 C400 110.8(9) . . ? O200 C300 H30A 109.5 . . ? C400 C300 H30A 109.5 . . ? O200 C300 H30B 109.5 . . ? C400 C300 H30B 109.5 . . ? H30A C300 H30B 108.1 . . ? O100 C400 C300 104.3(10) . . ? O100 C400 H40A 110.9 . . ? C300 C400 H40A 110.9 . . ? O100 C400 H40B 110.9 . . ? C300 C400 H40B 110.9 . . ? H40A C400 H40B 108.9 . . ? C200 O200 C300 106.5(8) . . ? 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 C3 O1 C2 C1 178.3(4) . . . . ? C2 O1 C3 O2 1.0(6) . . . . ? C2 O1 C3 N1 -177.9(4) . . . . ? C4 N1 C3 O2 -2.2(7) . . . . ? C4 N1 C3 O1 176.6(4) . . . . ? C5 N2 C4 N1 -172.1(3) . . . . ? C5 N2 C4 S1 7.0(6) . . . . ? C3 N1 C4 N2 0.9(6) . . . . ? C3 N1 C4 S1 -178.2(3) . . . . ? C4 N2 C5 C6 86.0(5) . . . . ? C4 N2 C5 C5 -97.6(5) . . . 2 ? C5 C5 C6 C7 -0.2(6) 2 . . . ? N2 C5 C6 C7 176.2(3) . . . . ? C5 C6 C7 C7 -1.4(6) . . . 2 ? C400 O100 C100 C200 41.0(16) 2 . . . ? C400 O100 C100 C200 -71.2(11) . . . . ? C100 O100 C100 C200 -41.7(8) 2 . . . ? O100 C100 C200 O200 66.8(15) . . . . ? C400 O100 C400 C300 40.6(7) 2 . . . ? C100 O100 C400 C300 -37.3(17) 2 . . . ? C100 O100 C400 C300 69.7(9) . . . . ? O200 C300 C400 O100 -66.0(14) . . . . ? C100 C200 O200 C300 -61.3(13) . . . . ? C400 C300 O200 C200 61.0(12) . . . . ? 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 H1N S1 0.90(2) 2.43(2) 3.298(3) 162(4) 7_556 N2 H2N O2 0.88(2) 1.99(4) 2.664(4) 132(4) . _diffrn_measured_fraction_theta_max 0.833 _diffrn_reflns_theta_full 67.07 _diffrn_measured_fraction_theta_full 0.833 _refine_diff_density_max 1.375 _refine_diff_density_min -0.518 _refine_diff_density_rms 0.085 data_TE-dioxaneII _database_code_depnum_ccdc_archive 'CCDC 770749' #TrackingRef '- TE_structures2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 N4 O4 S2, C4 H8 O2' _chemical_formula_sum 'C18 H26 N4 O6 S2' _chemical_formula_weight 458.55 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2924(2) _cell_length_b 11.7070(3) _cell_length_c 12.1305(3) _cell_angle_alpha 65.555(2) _cell_angle_beta 68.864(2) _cell_angle_gamma 76.329(3) _cell_volume 1114.61(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.366 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 2.528 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5176 _exptl_absorpt_correction_T_max 0.7861 _exptl_absorpt_process_details ; Denzo (Otwinowski, Borek, Majewski & Minor,2003) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5447 _diffrn_reflns_av_R_equivalents 0.0504 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.17 _diffrn_reflns_theta_max 67.11 _reflns_number_total 3818 _reflns_number_gt 3123 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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. The N-H hydrogen atoms found in the electron density map were restrained to a distance of 0.91 \%A to give the best fit to the X-ray data and to ensure stable refinement ; _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^)+(0.0548P)^2^+0.6176P] 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 3818 _refine_ls_number_parameters 285 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1175 _refine_ls_wR_factor_gt 0.1089 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.023 _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 0.75610(9) 0.13148(7) 0.76374(6) 0.0510(2) Uani 1 1 d . . . S2 S 1.12418(7) 0.41109(5) 0.14367(6) 0.03919(19) Uani 1 1 d . . . O1 O 0.6579(2) 0.33131(19) 0.38168(16) 0.0507(5) Uani 1 1 d . . . O2 O 0.4182(2) 0.36128(18) 0.50731(16) 0.0460(5) Uani 1 1 d . . . O3 O 0.7759(2) 0.15314(16) 0.20795(16) 0.0448(5) Uani 1 1 d . . . O4 O 0.71683(19) 0.32386(15) 0.04851(15) 0.0383(4) Uani 1 1 d . . . N1 N 0.6003(2) 0.2534(2) 0.59890(19) 0.0386(5) Uani 1 1 d D . . H1N H 0.523(3) 0.254(3) 0.667(2) 0.046 Uiso 1 1 d D . . N2 N 0.8574(2) 0.20037(19) 0.50941(18) 0.0352(5) Uani 1 1 d D . . H2N H 0.824(3) 0.240(2) 0.442(2) 0.042 Uiso 1 1 d D . . N3 N 1.0024(2) 0.19220(18) 0.27579(17) 0.0310(4) Uani 1 1 d D . . H3N H 0.931(3) 0.145(2) 0.290(2) 0.037 Uiso 1 1 d D . . N4 N 0.9052(2) 0.33107(18) 0.11234(17) 0.0308(4) Uani 1 1 d D . . H4N H 0.904(3) 0.4050(18) 0.051(2) 0.037 Uiso 1 1 d D . . C1 C 0.1992(3) 0.4728(3) 0.4373(3) 0.0571(8) Uani 1 1 d . . . H1A H 0.1408 0.3992 0.4898 0.086 Uiso 1 1 calc R . . H1B H 0.1622 0.5224 0.3632 0.086 Uiso 1 1 calc R . . H1C H 0.1843 0.5249 0.4870 0.086 Uiso 1 1 calc R . . C2 C 0.3674(3) 0.4298(3) 0.3944(3) 0.0528(7) Uani 1 1 d . . . H2A H 0.3836 0.3742 0.3469 0.063 Uiso 1 1 calc R . . H2B H 0.4272 0.5033 0.3382 0.063 Uiso 1 1 calc R . . C3 C 0.5670(3) 0.3164(2) 0.4858(2) 0.0398(6) Uani 1 1 d . . . C4 C 0.7444(3) 0.1960(2) 0.6167(2) 0.0358(6) Uani 1 1 d . . . C5 C 1.0159(3) 0.1560(2) 0.4842(2) 0.0321(5) Uani 1 1 d . . . C6 C 1.1013(3) 0.1183(2) 0.5700(2) 0.0392(6) Uani 1 1 d . . . H6 H 1.0516 0.1159 0.6543 0.047 Uiso 1 1 calc R . . C7 C 1.2588(3) 0.0846(3) 0.5306(3) 0.0474(7) Uani 1 1 d . . . H7 H 1.3172 0.0598 0.5885 0.057 Uiso 1 1 calc R . . C8 C 1.3333(3) 0.0862(3) 0.4090(3) 0.0507(7) Uani 1 1 d . . . H8 H 1.4420 0.0637 0.3832 0.061 Uiso 1 1 calc R . . C9 C 1.2485(3) 0.1209(2) 0.3246(3) 0.0413(6) Uani 1 1 d . . . H9 H 1.2985 0.1208 0.2411 0.050 Uiso 1 1 calc R . . C10 C 1.0914(3) 0.1556(2) 0.3621(2) 0.0318(5) Uani 1 1 d . . . C11 C 1.0057(3) 0.3043(2) 0.1812(2) 0.0299(5) Uani 1 1 d . . . C12 C 0.7960(3) 0.2581(2) 0.1306(2) 0.0335(5) Uani 1 1 d . . . C13 C 0.5998(4) 0.2636(3) 0.0458(3) 0.0579(8) Uani 1 1 d . . . H13A H 0.5152 0.2456 0.1270 0.069 Uiso 1 1 calc R . . H13B H 0.6455 0.1832 0.0326 0.069 Uiso 1 1 calc R . . C14 C 0.5394(3) 0.3519(3) -0.0602(3) 0.0512(7) Uani 1 1 d . . . H14A H 0.4982 0.4322 -0.0475 0.077 Uiso 1 1 calc R . . H14B H 0.4566 0.3157 -0.0632 0.077 Uiso 1 1 calc R . . H14C H 0.6235 0.3664 -0.1402 0.077 Uiso 1 1 calc R . . O100 O 0.0330(2) 0.17652(17) 0.92248(17) 0.0464(5) Uani 1 1 d . . . O200 O 0.3385(2) 0.24582(16) 0.81262(16) 0.0415(4) Uani 1 1 d . . . C100 C 0.1638(3) 0.0841(3) 0.9271(3) 0.0493(7) Uani 1 1 d . . . H10A H 0.1935 0.0572 0.8538 0.059 Uiso 1 1 calc R . . H10B H 0.1365 0.0092 1.0056 0.059 Uiso 1 1 calc R . . C200 C 0.2988(3) 0.1365(3) 0.9243(3) 0.0453(6) Uani 1 1 d . . . H20A H 0.2713 0.1588 1.0002 0.054 Uiso 1 1 calc R . . H20B H 0.3892 0.0717 0.9261 0.054 Uiso 1 1 calc R . . C300 C 0.2071(3) 0.3382(2) 0.8078(2) 0.0395(6) Uani 1 1 d . . . H30A H 0.2343 0.4129 0.7290 0.047 Uiso 1 1 calc R . . H30B H 0.1775 0.3656 0.8808 0.047 Uiso 1 1 calc R . . C400 C 0.0731(3) 0.2854(2) 0.8112(2) 0.0417(6) Uani 1 1 d . . . H40A H -0.0173 0.3502 0.8092 0.050 Uiso 1 1 calc R . . H40B H 0.1006 0.2629 0.7353 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 S1 0.0530(4) 0.0641(5) 0.0288(3) -0.0141(3) -0.0167(3) 0.0089(3) S2 0.0413(4) 0.0326(3) 0.0441(4) -0.0026(3) -0.0227(3) -0.0097(3) O1 0.0362(10) 0.0732(13) 0.0279(9) -0.0102(9) -0.0098(8) 0.0055(9) O2 0.0327(10) 0.0577(11) 0.0355(9) -0.0098(8) -0.0118(8) 0.0060(8) O3 0.0574(12) 0.0400(10) 0.0366(10) 0.0012(8) -0.0216(8) -0.0205(9) O4 0.0384(10) 0.0378(9) 0.0389(9) -0.0028(7) -0.0190(8) -0.0132(7) N1 0.0335(12) 0.0473(12) 0.0272(10) -0.0111(9) -0.0076(9) 0.0031(9) N2 0.0326(11) 0.0438(12) 0.0268(10) -0.0105(9) -0.0121(9) 0.0011(9) N3 0.0317(11) 0.0311(10) 0.0279(10) -0.0057(8) -0.0107(8) -0.0055(8) N4 0.0350(11) 0.0290(10) 0.0263(10) -0.0039(8) -0.0117(8) -0.0067(8) C1 0.0401(16) 0.0639(19) 0.0561(18) -0.0104(15) -0.0212(14) 0.0044(14) C2 0.0424(16) 0.0648(18) 0.0375(15) -0.0069(13) -0.0174(12) 0.0056(13) C3 0.0351(14) 0.0450(14) 0.0332(14) -0.0103(11) -0.0096(11) -0.0013(11) C4 0.0380(14) 0.0355(13) 0.0335(13) -0.0125(10) -0.0125(11) -0.0001(10) C5 0.0332(13) 0.0272(11) 0.0340(12) -0.0050(9) -0.0147(10) -0.0038(10) C6 0.0434(15) 0.0386(13) 0.0351(13) -0.0058(11) -0.0194(11) -0.0050(11) C7 0.0431(16) 0.0462(15) 0.0479(16) -0.0016(12) -0.0265(13) -0.0037(12) C8 0.0330(14) 0.0488(16) 0.0517(17) 0.0001(13) -0.0164(13) 0.0006(12) C9 0.0342(14) 0.0382(14) 0.0393(14) -0.0062(11) -0.0090(11) 0.0005(11) C10 0.0331(13) 0.0256(11) 0.0331(12) -0.0038(9) -0.0132(10) -0.0045(9) C11 0.0276(12) 0.0331(12) 0.0265(11) -0.0129(10) -0.0054(9) 0.0008(9) C12 0.0369(14) 0.0360(13) 0.0260(12) -0.0092(10) -0.0075(10) -0.0077(11) C13 0.065(2) 0.0629(19) 0.0545(18) -0.0035(14) -0.0314(15) -0.0325(16) C14 0.0464(17) 0.0576(17) 0.0631(18) -0.0241(14) -0.0299(14) -0.0040(13) O100 0.0405(10) 0.0440(10) 0.0514(11) -0.0101(8) -0.0143(8) -0.0107(8) O200 0.0358(10) 0.0444(10) 0.0356(9) -0.0093(8) -0.0064(7) -0.0051(8) C100 0.0540(18) 0.0378(14) 0.0533(17) -0.0071(12) -0.0214(14) -0.0088(13) C200 0.0430(15) 0.0451(15) 0.0396(14) -0.0040(12) -0.0148(12) -0.0074(12) C300 0.0389(14) 0.0370(13) 0.0389(14) -0.0145(11) -0.0067(11) -0.0034(11) C400 0.0437(15) 0.0388(14) 0.0425(14) -0.0117(11) -0.0178(12) -0.0015(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 C4 1.658(2) . ? S2 C11 1.674(2) . ? O1 C3 1.207(3) . ? O2 C3 1.329(3) . ? O2 C2 1.456(3) . ? O3 C12 1.206(3) . ? O4 C12 1.323(3) . ? O4 C13 1.445(3) . ? N1 C3 1.372(3) . ? N1 C4 1.397(3) . ? N1 H1N 0.882(17) . ? N2 C4 1.335(3) . ? N2 C5 1.406(3) . ? N2 H2N 0.881(17) . ? N3 C11 1.337(3) . ? N3 C10 1.432(3) . ? N3 H3N 0.881(16) . ? N4 C11 1.369(3) . ? N4 C12 1.378(3) . ? N4 H4N 0.880(16) . ? C1 C2 1.491(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C5 C10 1.393(3) . ? C5 C6 1.399(3) . ? C6 C7 1.379(4) . ? C6 H6 0.9500 . ? C7 C8 1.380(4) . ? C7 H7 0.9500 . ? C8 C9 1.385(4) . ? C8 H8 0.9500 . ? C9 C10 1.377(3) . ? C9 H9 0.9500 . ? C13 C14 1.478(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? O100 C400 1.422(3) . ? O100 C100 1.425(3) . ? O200 C200 1.427(3) . ? O200 C300 1.428(3) . ? C100 C200 1.505(4) . ? C100 H10A 0.9900 . ? C100 H10B 0.9900 . ? C200 H20A 0.9900 . ? C200 H20B 0.9900 . ? C300 C400 1.497(4) . ? C300 H30A 0.9900 . ? C300 H30B 0.9900 . ? C400 H40A 0.9900 . ? C400 H40B 0.9900 . ? 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 C3 O2 C2 115.21(19) . . ? C12 O4 C13 117.88(19) . . ? C3 N1 C4 127.3(2) . . ? C3 N1 H1N 115.7(19) . . ? C4 N1 H1N 116.9(19) . . ? C4 N2 C5 132.7(2) . . ? C4 N2 H2N 111.9(18) . . ? C5 N2 H2N 115.4(18) . . ? C11 N3 C10 123.04(19) . . ? C11 N3 H3N 116.3(17) . . ? C10 N3 H3N 120.0(17) . . ? C11 N4 C12 128.04(19) . . ? C11 N4 H4N 118.7(17) . . ? C12 N4 H4N 113.2(17) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 C1 107.3(2) . . ? O2 C2 H2A 110.2 . . ? C1 C2 H2A 110.2 . . ? O2 C2 H2B 110.2 . . ? C1 C2 H2B 110.2 . . ? H2A C2 H2B 108.5 . . ? O1 C3 O2 124.3(2) . . ? O1 C3 N1 126.0(2) . . ? O2 C3 N1 109.7(2) . . ? N2 C4 N1 114.0(2) . . ? N2 C4 S1 127.99(19) . . ? N1 C4 S1 118.00(18) . . ? C10 C5 C6 119.1(2) . . ? C10 C5 N2 115.9(2) . . ? C6 C5 N2 125.0(2) . . ? C7 C6 C5 119.2(2) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C6 C7 C8 121.4(2) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C7 C8 C9 119.6(3) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 119.8(3) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C5 120.9(2) . . ? C9 C10 N3 120.4(2) . . ? C5 C10 N3 118.7(2) . . ? N3 C11 N4 116.9(2) . . ? N3 C11 S2 123.82(18) . . ? N4 C11 S2 119.24(17) . . ? O3 C12 O4 126.1(2) . . ? O3 C12 N4 126.0(2) . . ? O4 C12 N4 107.92(19) . . ? O4 C13 C14 107.0(2) . . ? O4 C13 H13A 110.3 . . ? C14 C13 H13A 110.3 . . ? O4 C13 H13B 110.3 . . ? C14 C13 H13B 110.3 . . ? H13A C13 H13B 108.6 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C400 O100 C100 109.7(2) . . ? C200 O200 C300 109.77(19) . . ? O100 C100 C200 110.6(2) . . ? O100 C100 H10A 109.5 . . ? C200 C100 H10A 109.5 . . ? O100 C100 H10B 109.5 . . ? C200 C100 H10B 109.5 . . ? H10A C100 H10B 108.1 . . ? O200 C200 C100 110.4(2) . . ? O200 C200 H20A 109.6 . . ? C100 C200 H20A 109.6 . . ? O200 C200 H20B 109.6 . . ? C100 C200 H20B 109.6 . . ? H20A C200 H20B 108.1 . . ? O200 C300 C400 110.6(2) . . ? O200 C300 H30A 109.5 . . ? C400 C300 H30A 109.5 . . ? O200 C300 H30B 109.5 . . ? C400 C300 H30B 109.5 . . ? H30A C300 H30B 108.1 . . ? O100 C400 C300 110.9(2) . . ? O100 C400 H40A 109.5 . . ? C300 C400 H40A 109.5 . . ? O100 C400 H40B 109.5 . . ? C300 C400 H40B 109.5 . . ? H40A C400 H40B 108.1 . . ? 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 C3 O2 C2 C1 -179.8(2) . . . . ? C2 O2 C3 O1 1.4(4) . . . . ? C2 O2 C3 N1 -179.6(2) . . . . ? C4 N1 C3 O1 1.0(5) . . . . ? C4 N1 C3 O2 -178.0(2) . . . . ? C5 N2 C4 N1 179.7(2) . . . . ? C5 N2 C4 S1 -0.6(4) . . . . ? C3 N1 C4 N2 -3.2(4) . . . . ? C3 N1 C4 S1 177.0(2) . . . . ? C4 N2 C5 C10 167.6(2) . . . . ? C4 N2 C5 C6 -15.2(4) . . . . ? C10 C5 C6 C7 1.5(3) . . . . ? N2 C5 C6 C7 -175.6(2) . . . . ? C5 C6 C7 C8 -0.6(4) . . . . ? C6 C7 C8 C9 -0.7(4) . . . . ? C7 C8 C9 C10 1.2(4) . . . . ? C8 C9 C10 C5 -0.2(4) . . . . ? C8 C9 C10 N3 179.8(2) . . . . ? C6 C5 C10 C9 -1.1(3) . . . . ? N2 C5 C10 C9 176.3(2) . . . . ? C6 C5 C10 N3 178.9(2) . . . . ? N2 C5 C10 N3 -3.7(3) . . . . ? C11 N3 C10 C9 -75.7(3) . . . . ? C11 N3 C10 C5 104.2(3) . . . . ? C10 N3 C11 N4 -174.7(2) . . . . ? C10 N3 C11 S2 5.3(3) . . . . ? C12 N4 C11 N3 2.3(3) . . . . ? C12 N4 C11 S2 -177.74(19) . . . . ? C13 O4 C12 O3 -3.2(4) . . . . ? C13 O4 C12 N4 177.1(2) . . . . ? C11 N4 C12 O3 -4.3(4) . . . . ? C11 N4 C12 O4 175.5(2) . . . . ? C12 O4 C13 C14 -175.1(2) . . . . ? C400 O100 C100 C200 57.9(3) . . . . ? C300 O200 C200 C100 57.6(3) . . . . ? O100 C100 C200 O200 -58.3(3) . . . . ? C200 O200 C300 C400 -57.6(3) . . . . ? C100 O100 C400 C300 -57.9(3) . . . . ? O200 C300 C400 O100 58.2(3) . . . . ? 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 H1N O200 0.882(17) 1.953(18) 2.831(3) 173(3) . N2 H2N O1 0.881(17) 1.86(2) 2.636(3) 146(3) . N3 H3N O3 0.881(16) 2.00(2) 2.708(3) 137(2) . N4 H4N S2 0.880(16) 2.497(18) 3.3607(19) 167(2) 2_765 _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 67.11 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.267 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.053 data_TE-pyridine _database_code_depnum_ccdc_archive 'CCDC 770750' #TrackingRef '- TE_structures2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 N4 O4 S2, C5 H5 N' _chemical_formula_sum 'C19 H23 N5 O4 S2' _chemical_formula_weight 449.54 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 8.8104(9) _cell_length_b 11.3513(13) _cell_length_c 12.500(2) _cell_angle_alpha 66.635(7) _cell_angle_beta 77.989(6) _cell_angle_gamma 77.883(5) _cell_volume 1111.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.274 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9271 _exptl_absorpt_correction_T_max 0.9731 _exptl_absorpt_process_details ; Denzo (Otwinowski, Borek, Majewski & Minor,2003) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6213 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 25.34 _reflns_number_total 4056 _reflns_number_gt 3140 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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. The N-H hydrogen atoms found in the electron density map were restrained to a distance of 0.91 \%A to give the best fit to the X-ray data and to ensure stable refinement ; _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^)+(0.0064P)^2^+1.7365P] 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 4056 _refine_ls_number_parameters 285 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0757 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.33580(9) 0.21261(8) 0.59683(7) 0.0354(2) Uani 1 1 d . . . S2 S -0.08862(10) 0.38481(8) 0.93043(7) 0.0341(2) Uani 1 1 d . . . O1 O 0.1791(2) -0.0083(2) 0.98719(18) 0.0342(5) Uani 1 1 d . . . O2 O 0.4261(2) -0.11348(19) 0.97324(17) 0.0285(5) Uani 1 1 d . . . O3 O 0.3103(2) 0.5837(2) 0.66638(18) 0.0339(5) Uani 1 1 d . . . O4 O 0.3099(3) 0.6578(2) 0.8106(2) 0.0375(5) Uani 1 1 d . . . N1 N 0.3494(3) 0.0426(2) 0.8130(2) 0.0238(5) Uani 1 1 d D . . H1N H 0.450(2) 0.024(3) 0.784(3) 0.029 Uiso 1 1 d D . . N2 N 0.1069(3) 0.1662(2) 0.7783(2) 0.0245(5) Uani 1 1 d D . . H2N H 0.072(3) 0.123(3) 0.8534(17) 0.029 Uiso 1 1 d D . . N3 N 0.0779(3) 0.4411(2) 0.7180(2) 0.0235(5) Uani 1 1 d D . . H3N H 0.155(3) 0.480(3) 0.664(2) 0.028 Uiso 1 1 d D . . N4 N 0.1452(3) 0.5220(2) 0.8424(2) 0.0239(5) Uani 1 1 d D . . H4N H 0.124(3) 0.531(3) 0.9118(19) 0.029 Uiso 1 1 d D . . C1 C 0.5428(4) -0.2912(3) 1.1254(3) 0.0371(8) Uani 1 1 d . . . H1A H 0.5540 -0.3490 1.0823 0.056 Uiso 1 1 calc R . . H1B H 0.5339 -0.3422 1.2101 0.056 Uiso 1 1 calc R . . H1C H 0.6348 -0.2461 1.1011 0.056 Uiso 1 1 calc R . . C3 C 0.3048(3) -0.0253(3) 0.9304(3) 0.0250(6) Uani 1 1 d . . . C2 C 0.3980(3) -0.1935(3) 1.0988(3) 0.0289(7) Uani 1 1 d . . . H2A H 0.3052 -0.2376 1.1159 0.035 Uiso 1 1 calc R . . H2B H 0.3797 -0.1393 1.1470 0.035 Uiso 1 1 calc R . . C4 C 0.2566(3) 0.1390(3) 0.7355(2) 0.0227(6) Uani 1 1 d . . . C5 C -0.0074(3) 0.2545(3) 0.7065(2) 0.0207(6) Uani 1 1 d . . . C6 C -0.1064(3) 0.2053(3) 0.6668(3) 0.0262(6) Uani 1 1 d . . . H6 H -0.0942 0.1148 0.6837 0.031 Uiso 1 1 calc R . . C7 C -0.2236(3) 0.2879(3) 0.6025(3) 0.0280(7) Uani 1 1 d . . . H7 H -0.2917 0.2537 0.5759 0.034 Uiso 1 1 calc R . . C8 C -0.2411(3) 0.4196(3) 0.5771(3) 0.0287(7) Uani 1 1 d . . . H8 H -0.3219 0.4759 0.5339 0.034 Uiso 1 1 calc R . . C9 C -0.1402(3) 0.4695(3) 0.6149(2) 0.0261(6) Uani 1 1 d . . . H9 H -0.1504 0.5603 0.5959 0.031 Uiso 1 1 calc R . . C10 C -0.0243(3) 0.3865(3) 0.6805(2) 0.0219(6) Uani 1 1 d . . . C11 C 0.0512(3) 0.4514(3) 0.8223(3) 0.0218(6) Uani 1 1 d . . . C12 C 0.2617(3) 0.5879(3) 0.7624(3) 0.0257(6) Uani 1 1 d . . . C13 C 0.4464(4) 0.7222(3) 0.7457(3) 0.0418(9) Uani 1 1 d . . . H13A H 0.4375 0.8049 0.7573 0.050 Uiso 1 1 calc R . . H13B H 0.4514 0.7420 0.6605 0.050 Uiso 1 1 calc R . . C14 C 0.5910(4) 0.6362(4) 0.7885(4) 0.0613(12) Uani 1 1 d . . . H14A H 0.5838 0.6145 0.8734 0.092 Uiso 1 1 calc R . . H14B H 0.6823 0.6808 0.7475 0.092 Uiso 1 1 calc R . . H14C H 0.6021 0.5564 0.7730 0.092 Uiso 1 1 calc R . . N5 N 0.6672(3) -0.0467(2) 0.7303(2) 0.0281(6) Uani 1 1 d . . . C15 C 0.7058(4) -0.0391(3) 0.6190(3) 0.0315(7) Uani 1 1 d . . . H15 H 0.6321 0.0078 0.5657 0.038 Uiso 1 1 calc R . . C16 C 0.8477(4) -0.0961(3) 0.5775(3) 0.0394(8) Uani 1 1 d . . . H16 H 0.8697 -0.0908 0.4982 0.047 Uiso 1 1 calc R . . C17 C 0.9571(4) -0.1612(3) 0.6540(3) 0.0416(8) Uani 1 1 d . . . H17 H 1.0565 -0.1997 0.6274 0.050 Uiso 1 1 calc R . . C18 C 0.9200(4) -0.1694(3) 0.7692(3) 0.0374(8) Uani 1 1 d . . . H18 H 0.9930 -0.2135 0.8235 0.045 Uiso 1 1 calc R . . C19 C 0.7737(4) -0.1118(3) 0.8036(3) 0.0314(7) Uani 1 1 d . . . H19 H 0.7473 -0.1187 0.8834 0.038 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 S1 0.0275(4) 0.0410(5) 0.0245(4) -0.0029(3) -0.0009(3) 0.0016(3) S2 0.0366(4) 0.0472(5) 0.0263(4) -0.0180(4) 0.0044(3) -0.0218(4) O1 0.0242(11) 0.0419(13) 0.0244(11) -0.0053(10) -0.0014(9) 0.0046(9) O2 0.0226(10) 0.0300(11) 0.0239(11) -0.0037(9) -0.0050(8) 0.0043(8) O3 0.0352(12) 0.0448(13) 0.0223(11) -0.0094(10) -0.0019(9) -0.0150(10) O4 0.0337(12) 0.0446(14) 0.0446(14) -0.0250(11) 0.0044(10) -0.0196(10) N1 0.0185(12) 0.0259(13) 0.0230(13) -0.0075(10) -0.0034(10) 0.0024(10) N2 0.0222(12) 0.0265(13) 0.0195(13) -0.0049(10) -0.0039(10) 0.0017(10) N3 0.0238(12) 0.0270(13) 0.0213(13) -0.0089(10) -0.0029(10) -0.0072(10) N4 0.0252(12) 0.0278(13) 0.0229(13) -0.0123(11) -0.0031(10) -0.0068(10) C1 0.0400(18) 0.0314(18) 0.0306(18) -0.0042(14) -0.0103(14) 0.0053(14) C3 0.0271(15) 0.0252(15) 0.0249(15) -0.0109(12) -0.0060(12) -0.0027(12) C2 0.0298(16) 0.0291(16) 0.0216(15) -0.0034(13) -0.0030(12) -0.0037(12) C4 0.0249(14) 0.0206(14) 0.0240(15) -0.0087(12) -0.0065(12) -0.0020(11) C5 0.0182(13) 0.0250(15) 0.0159(14) -0.0061(11) -0.0028(11) 0.0007(11) C6 0.0290(15) 0.0264(15) 0.0233(15) -0.0095(12) -0.0039(12) -0.0035(12) C7 0.0233(15) 0.0399(18) 0.0250(16) -0.0137(14) -0.0056(12) -0.0071(13) C8 0.0244(15) 0.0352(17) 0.0235(16) -0.0080(13) -0.0063(12) -0.0005(13) C9 0.0272(15) 0.0246(15) 0.0239(16) -0.0078(12) -0.0038(12) -0.0002(12) C10 0.0199(13) 0.0278(15) 0.0197(15) -0.0106(12) -0.0012(11) -0.0049(11) C11 0.0185(13) 0.0195(14) 0.0276(16) -0.0090(12) -0.0077(11) 0.0018(11) C12 0.0243(15) 0.0231(15) 0.0300(18) -0.0085(13) -0.0087(13) -0.0020(12) C13 0.0388(19) 0.045(2) 0.051(2) -0.0233(18) 0.0056(16) -0.0258(16) C14 0.034(2) 0.049(2) 0.102(4) -0.033(2) 0.006(2) -0.0128(17) N5 0.0234(12) 0.0266(13) 0.0320(15) -0.0085(11) -0.0023(11) -0.0048(10) C15 0.0288(16) 0.0351(18) 0.0305(17) -0.0102(14) -0.0038(13) -0.0084(13) C16 0.0388(19) 0.044(2) 0.0326(19) -0.0149(16) 0.0046(15) -0.0082(15) C17 0.0277(17) 0.0391(19) 0.049(2) -0.0152(17) 0.0048(15) 0.0018(14) C18 0.0320(17) 0.0318(18) 0.043(2) -0.0099(15) -0.0067(15) -0.0004(14) C19 0.0330(17) 0.0263(16) 0.0348(18) -0.0110(14) -0.0039(14) -0.0056(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 C4 1.668(3) . ? S2 C11 1.674(3) . ? O1 C3 1.208(3) . ? O2 C3 1.340(3) . ? O2 C2 1.467(3) . ? O3 C12 1.204(4) . ? O4 C12 1.341(4) . ? O4 C13 1.460(4) . ? N1 C3 1.376(4) . ? N1 C4 1.385(3) . ? N1 H1N 0.901(18) . ? N2 C4 1.337(4) . ? N2 C5 1.436(3) . ? N2 H2N 0.891(17) . ? N3 C11 1.323(4) . ? N3 C10 1.433(4) . ? N3 H3N 0.899(18) . ? N4 C12 1.384(4) . ? N4 C11 1.385(4) . ? N4 H4N 0.892(18) . ? C1 C2 1.502(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C5 C10 1.384(4) . ? C5 C6 1.388(4) . ? C6 C7 1.390(4) . ? C6 H6 0.9500 . ? C7 C8 1.381(4) . ? C7 H7 0.9500 . ? C8 C9 1.390(4) . ? C8 H8 0.9500 . ? C9 C10 1.391(4) . ? C9 H9 0.9500 . ? C13 C14 1.487(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? N5 C15 1.333(4) . ? N5 C19 1.340(4) . ? C15 C16 1.382(4) . ? C15 H15 0.9500 . ? C16 C17 1.382(5) . ? C16 H16 0.9500 . ? C17 C18 1.379(5) . ? C17 H17 0.9500 . ? C18 C19 1.383(4) . ? 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 C3 O2 C2 115.3(2) . . ? C12 O4 C13 116.3(2) . . ? C3 N1 C4 126.7(2) . . ? C3 N1 H1N 116.8(19) . . ? C4 N1 H1N 116(2) . . ? C4 N2 C5 123.2(2) . . ? C4 N2 H2N 119(2) . . ? C5 N2 H2N 117(2) . . ? C11 N3 C10 122.8(2) . . ? C11 N3 H3N 119(2) . . ? C10 N3 H3N 118(2) . . ? C12 N4 C11 126.5(3) . . ? C12 N4 H4N 116(2) . . ? C11 N4 H4N 117(2) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C3 O2 125.0(3) . . ? O1 C3 N1 126.6(3) . . ? O2 C3 N1 108.5(2) . . ? O2 C2 C1 106.3(2) . . ? O2 C2 H2A 110.5 . . ? C1 C2 H2A 110.5 . . ? O2 C2 H2B 110.5 . . ? C1 C2 H2B 110.5 . . ? H2A C2 H2B 108.7 . . ? N2 C4 N1 116.7(2) . . ? N2 C4 S1 124.3(2) . . ? N1 C4 S1 119.0(2) . . ? C10 C5 C6 119.7(2) . . ? C10 C5 N2 121.2(2) . . ? C6 C5 N2 119.1(2) . . ? C5 C6 C7 120.3(3) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C8 C7 C6 120.0(3) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 119.9(3) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C8 C9 C10 120.0(3) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C5 C10 C9 120.1(3) . . ? C5 C10 N3 121.2(2) . . ? C9 C10 N3 118.6(3) . . ? N3 C11 N4 117.5(3) . . ? N3 C11 S2 124.1(2) . . ? N4 C11 S2 118.4(2) . . ? O3 C12 O4 126.2(3) . . ? O3 C12 N4 125.9(3) . . ? O4 C12 N4 107.9(3) . . ? O4 C13 C14 109.4(3) . . ? O4 C13 H13A 109.8 . . ? C14 C13 H13A 109.8 . . ? O4 C13 H13B 109.8 . . ? C14 C13 H13B 109.8 . . ? H13A C13 H13B 108.2 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C15 N5 C19 117.5(3) . . ? N5 C15 C16 123.2(3) . . ? N5 C15 H15 118.4 . . ? C16 C15 H15 118.4 . . ? C15 C16 C17 118.6(3) . . ? C15 C16 H16 120.7 . . ? C17 C16 H16 120.7 . . ? C18 C17 C16 119.2(3) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C17 C18 C19 118.2(3) . . ? C17 C18 H18 120.9 . . ? C19 C18 H18 120.9 . . ? N5 C19 C18 123.3(3) . . ? N5 C19 H19 118.3 . . ? C18 C19 H19 118.3 . . ? 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 C2 O2 C3 O1 0.4(4) . . . . ? C2 O2 C3 N1 179.3(2) . . . . ? C4 N1 C3 O1 -3.7(5) . . . . ? C4 N1 C3 O2 177.5(3) . . . . ? C3 O2 C2 C1 175.6(3) . . . . ? C5 N2 C4 N1 -173.8(2) . . . . ? C5 N2 C4 S1 5.9(4) . . . . ? C3 N1 C4 N2 -2.1(4) . . . . ? C3 N1 C4 S1 178.1(2) . . . . ? C4 N2 C5 C10 -85.1(4) . . . . ? C4 N2 C5 C6 97.5(3) . . . . ? C10 C5 C6 C7 -0.9(4) . . . . ? N2 C5 C6 C7 176.6(3) . . . . ? C5 C6 C7 C8 0.5(4) . . . . ? C6 C7 C8 C9 0.7(4) . . . . ? C7 C8 C9 C10 -1.5(4) . . . . ? C6 C5 C10 C9 0.1(4) . . . . ? N2 C5 C10 C9 -177.3(3) . . . . ? C6 C5 C10 N3 -178.7(3) . . . . ? N2 C5 C10 N3 3.9(4) . . . . ? C8 C9 C10 C5 1.1(4) . . . . ? C8 C9 C10 N3 179.9(3) . . . . ? C11 N3 C10 C5 -87.0(3) . . . . ? C11 N3 C10 C9 94.3(3) . . . . ? C10 N3 C11 N4 -171.0(2) . . . . ? C10 N3 C11 S2 8.9(4) . . . . ? C12 N4 C11 N3 2.7(4) . . . . ? C12 N4 C11 S2 -177.3(2) . . . . ? C13 O4 C12 O3 -7.7(4) . . . . ? C13 O4 C12 N4 172.7(2) . . . . ? C11 N4 C12 O3 -7.9(5) . . . . ? C11 N4 C12 O4 171.7(2) . . . . ? C12 O4 C13 C14 -92.2(4) . . . . ? C19 N5 C15 C16 0.9(5) . . . . ? N5 C15 C16 C17 -1.9(5) . . . . ? C15 C16 C17 C18 1.4(5) . . . . ? C16 C17 C18 C19 0.0(5) . . . . ? C15 N5 C19 C18 0.6(4) . . . . ? C17 C18 C19 N5 -1.1(5) . . . . ? 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 H1N N5 0.901(18) 2.001(18) 2.894(3) 171(3) . N2 H2N O1 0.891(17) 2.00(2) 2.684(3) 133(3) . N3 H3N O3 0.899(18) 1.99(3) 2.692(3) 134(3) . N4 H4N S2 0.892(18) 2.451(19) 3.317(3) 164(3) 2_567 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.251 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.061 data_TE-toluene _database_code_depnum_ccdc_archive 'CCDC 770751' #TrackingRef '- TE_structures2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '3(C14 H18 N4 O4 S2), 2(C7 H8)' _chemical_formula_sum 'C56 H70 N12 O12 S6' _chemical_formula_weight 1295.60 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 tetragonal _symmetry_space_group_name_H-M P4322 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x, z+3/4' '-x, -y, z+1/2' 'y, -x, z+1/4' 'x, -y, -z+1/2' 'y, x, -z+1/4' '-x, y, -z' '-y, -x, -z+3/4' _cell_length_a 11.7631(2) _cell_length_b 11.7631(2) _cell_length_c 48.5257(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6714.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2728 _exptl_absorpt_coefficient_mu 2.420 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5829 _exptl_absorpt_correction_T_max 0.7129 _exptl_absorpt_process_details ; Denzo (Otwinowski, Borek, Majewski & Minor,2003) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11130 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0492 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -57 _diffrn_reflns_limit_l_max 57 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 66.89 _reflns_number_total 5685 _reflns_number_gt 4509 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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. The N-H hydrogen atoms found in the electron density map were restrained to a distance of 0.91 \%A to give the best fit to the X-ray data and to ensure stable refinement The bond distances in the disordered ethyl group of one of the TE molecules were restrained to be approximately equal (+- 0.02 \%A) to the undisordered ethyl group distances with SADI to keep the model together. The bonds in the disordered toluene were also set to be approximately equal to each other with SADI (+- 0.02 \%A). Restraints on TE ethyl group SADI C26 O8 C17 O6A C17 O6B SADI O8 C27 O6A C16A O6B C16B SADI C27 C28 C16A C15A C16B C15B Restraints on toluene SADI C31A C32A C32A C33A C33A C34A C34A C35A C35A C36A C36A C31A SADI C31B C32B C32B C33B C33B C34B C34B C35B C35B C36B C36B C31B SADI C30A C31A C30B C31B ; _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^)+(0.0460P)^2^+2.0760P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.41(2) _refine_ls_number_reflns 5685 _refine_ls_number_parameters 433 _refine_ls_number_restraints 46 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1084 _refine_ls_wR_factor_gt 0.0987 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.63126(7) 0.38481(10) 0.165505(17) 0.0587(3) Uani 1 1 d . . . O1 O 0.73122(19) 0.4676(2) 0.07684(4) 0.0512(6) Uani 1 1 d . . . O2 O 0.90639(18) 0.4708(2) 0.09553(4) 0.0543(7) Uani 1 1 d . . . N1 N 0.7604(2) 0.4433(2) 0.12327(5) 0.0427(6) Uani 1 1 d D . . H1N H 0.816(2) 0.442(3) 0.1356(6) 0.051 Uiso 1 1 d D . . N2 N 0.5707(2) 0.4138(2) 0.11359(5) 0.0360(6) Uani 1 1 d D . . H2N H 0.589(3) 0.434(3) 0.0967(4) 0.043 Uiso 1 1 d D . . C1 C 1.0812(3) 0.4839(5) 0.07138(9) 0.0837(15) Uani 1 1 d . . . H1A H 1.1046 0.5451 0.0839 0.126 Uiso 1 1 calc R . . H1B H 1.1177 0.4943 0.0534 0.126 Uiso 1 1 calc R . . H1C H 1.1040 0.4104 0.0792 0.126 Uiso 1 1 calc R . . C2 C 0.9547(3) 0.4865(4) 0.06792(7) 0.0632(11) Uani 1 1 d . . . H2A H 0.9303 0.5603 0.0601 0.076 Uiso 1 1 calc R . . H2B H 0.9295 0.4249 0.0554 0.076 Uiso 1 1 calc R . . C3 C 0.7939(3) 0.4615(3) 0.09651(6) 0.0436(8) Uani 1 1 d . . . C4 C 0.6525(3) 0.4152(3) 0.13232(6) 0.0382(7) Uani 1 1 d . . . C5 C 0.4565(2) 0.3790(2) 0.11980(5) 0.0303(6) Uani 1 1 d . . . C6 C 0.4233(3) 0.2683(3) 0.11463(6) 0.0355(7) Uani 1 1 d . . . H6 H 0.4763 0.2150 0.1075 0.043 Uiso 1 1 calc R . . C7 C 0.3123(3) 0.2355(3) 0.11990(6) 0.0357(7) Uani 1 1 d . . . H7 H 0.2893 0.1594 0.1164 0.043 Uiso 1 1 calc R . . S3 S 0.44509(9) -0.01603(7) 0.084888(16) 0.0532(3) Uani 1 1 d . A . S4 S 0.17750(8) 0.19835(11) -0.001065(18) 0.0679(3) Uani 1 1 d . . . O5 O 0.3627(3) -0.1259(2) -0.00297(5) 0.0839(10) Uani 1 1 d . A . O7 O 0.0784(2) 0.1574(3) 0.08898(5) 0.0639(8) Uani 1 1 d . . . O8 O -0.09825(18) 0.1591(2) 0.07141(4) 0.0506(6) Uani 1 1 d D . . N5 N 0.3924(3) -0.1499(2) 0.04347(6) 0.0557(8) Uani 1 1 d D A . H5N H 0.391(3) -0.204(3) 0.0566(6) 0.067 Uiso 1 1 d D . . N6 N 0.4041(2) 0.0406(2) 0.03304(5) 0.0412(6) Uani 1 1 d D A . H6N H 0.383(3) 0.019(3) 0.0159(4) 0.049 Uiso 1 1 d D . . N7 N 0.2367(2) 0.2001(2) 0.05150(5) 0.0438(7) Uani 1 1 d D . . H7N H 0.209(3) 0.195(3) 0.0693(4) 0.053 Uiso 1 1 d D . . N8 N 0.0459(2) 0.1733(3) 0.04259(5) 0.0505(8) Uani 1 1 d D . . H8N H -0.010(2) 0.171(3) 0.0300(6) 0.061 Uiso 1 1 d D . . O6A O 0.3917(9) -0.3028(8) 0.0176(2) 0.069(3) Uani 0.50 1 d PD A 1 C15A C 0.2482(14) -0.4004(14) -0.0089(4) 0.118(8) Uani 0.50 1 d PD A 1 H15A H 0.2299 -0.4448 0.0076 0.178 Uiso 0.50 1 calc PR A 1 H15B H 0.2349 -0.4468 -0.0254 0.178 Uiso 0.50 1 calc PR A 1 H15C H 0.1998 -0.3326 -0.0096 0.178 Uiso 0.50 1 calc PR A 1 C16A C 0.3669(11) -0.3662(9) -0.00800(19) 0.071(3) Uani 0.50 1 d PD A 1 H16A H 0.3843 -0.3177 -0.0241 0.085 Uiso 0.50 1 calc PR A 1 H16B H 0.4159 -0.4345 -0.0089 0.085 Uiso 0.50 1 calc PR A 1 O6B O 0.3371(9) -0.2951(8) 0.0164(2) 0.063(3) Uani 0.50 1 d PD A 2 C15B C 0.2630(12) -0.4524(9) -0.0051(3) 0.062(3) Uani 0.50 1 d PD A 2 H15D H 0.3249 -0.4978 0.0028 0.092 Uiso 0.50 1 calc PR A 2 H15E H 0.2368 -0.4876 -0.0223 0.092 Uiso 0.50 1 calc PR A 2 H15F H 0.1998 -0.4489 0.0081 0.092 Uiso 0.50 1 calc PR A 2 C16B C 0.3033(14) -0.3390(9) -0.0107(2) 0.073(4) Uani 0.50 1 d PD A 2 H16C H 0.2423 -0.2917 -0.0189 0.087 Uiso 0.50 1 calc PR A 2 H16D H 0.3688 -0.3406 -0.0235 0.087 Uiso 0.50 1 calc PR A 2 C17 C 0.3718(4) -0.1859(3) 0.01691(7) 0.0709(13) Uani 1 1 d D . . C18 C 0.4127(3) -0.0404(3) 0.05209(6) 0.0401(7) Uani 1 1 d . . . C19 C 0.4321(3) 0.1567(3) 0.03784(6) 0.0357(7) Uani 1 1 d . . . C20 C 0.5433(3) 0.1919(3) 0.03353(6) 0.0402(7) Uani 1 1 d . A . H20 H 0.5997 0.1382 0.0284 0.048 Uiso 1 1 calc R . . C21 C 0.5720(3) 0.3056(3) 0.03676(6) 0.0409(8) Uani 1 1 d . . . H21 H 0.6480 0.3297 0.0337 0.049 Uiso 1 1 calc R A . C22 C 0.4908(3) 0.3830(3) 0.04437(6) 0.0405(8) Uani 1 1 d . A . H22 H 0.5106 0.4607 0.0467 0.049 Uiso 1 1 calc R . . C23 C 0.3792(3) 0.3478(3) 0.04873(6) 0.0401(7) Uani 1 1 d . . . H23 H 0.3228 0.4014 0.0540 0.048 Uiso 1 1 calc R A . C24 C 0.3507(2) 0.2346(3) 0.04534(6) 0.0365(7) Uani 1 1 d . A . C25 C 0.1551(3) 0.1910(3) 0.03292(6) 0.0432(8) Uani 1 1 d . . . C26 C 0.0138(3) 0.1624(3) 0.06976(6) 0.0477(9) Uani 1 1 d D . . C27 C -0.1430(3) 0.1414(4) 0.09916(7) 0.0585(10) Uani 1 1 d D . . H27A H -0.1163 0.2021 0.1117 0.070 Uiso 1 1 calc R . . H27B H -0.1176 0.0671 0.1065 0.070 Uiso 1 1 calc R . . C28 C -0.2693(3) 0.1442(4) 0.09672(8) 0.0619(10) Uani 1 1 d D . . H28A H -0.2926 0.2152 0.0878 0.093 Uiso 1 1 calc R . . H28B H -0.3033 0.1397 0.1151 0.093 Uiso 1 1 calc R . . H28C H -0.2949 0.0795 0.0856 0.093 Uiso 1 1 calc R . . C30A C -0.2688(15) 0.7829(16) 0.0835(4) 0.183(8) Uiso 0.50 1 d PD B 1 H31A H -0.3062 0.7413 0.0686 0.274 Uiso 0.50 1 calc PR B 1 H31B H -0.3141 0.8499 0.0883 0.274 Uiso 0.50 1 calc PR B 1 H31C H -0.2620 0.7334 0.0997 0.274 Uiso 0.50 1 calc PR B 1 C31A C -0.1554(12) 0.8188(13) 0.0746(3) 0.120(5) Uiso 0.50 1 d PD B 1 C32A C -0.1535(14) 0.8760(12) 0.0504(3) 0.105(4) Uiso 0.50 1 d PD B 1 H32A H -0.2219 0.8964 0.0413 0.126 Uiso 0.50 1 calc PR B 1 C33A C -0.0464(12) 0.9043(11) 0.0393(3) 0.108(4) Uiso 0.50 1 d PD B 1 H33A H -0.0504 0.9491 0.0230 0.130 Uiso 0.50 1 calc PR B 1 C34A C 0.0643(19) 0.8789(18) 0.0477(4) 0.148(7) Uiso 0.50 1 d PD B 1 H34A H 0.1324 0.8943 0.0378 0.178 Uiso 0.50 1 calc PR B 1 C35A C 0.0549(14) 0.8273(15) 0.0728(4) 0.144(6) Uiso 0.50 1 d PD B 1 H35A H 0.1233 0.8149 0.0828 0.173 Uiso 0.50 1 calc PR B 1 C36A C -0.0479(12) 0.7904(13) 0.0856(3) 0.106(4) Uiso 0.50 1 d PD B 1 H36A H -0.0439 0.7457 0.1018 0.127 Uiso 0.50 1 calc PR B 1 C30B C 0.1124(18) 0.866(3) 0.0442(6) 0.232(14) Uiso 0.50 1 d PD C 2 H30D H 0.1643 0.8133 0.0535 0.347 Uiso 0.50 1 calc PR C 2 H30E H 0.1409 0.9440 0.0462 0.347 Uiso 0.50 1 calc PR C 2 H30F H 0.1078 0.8467 0.0246 0.347 Uiso 0.50 1 calc PR C 2 C31B C -0.0016(9) 0.8576(10) 0.0567(2) 0.092(3) Uiso 0.50 1 d PD C 2 C32B C 0.0075(14) 0.8009(11) 0.0805(2) 0.097(3) Uiso 0.50 1 d PD C 2 H32B H 0.0800 0.7811 0.0877 0.116 Uiso 0.50 1 calc PR C 2 C33B C -0.0919(11) 0.7716(12) 0.0945(3) 0.111(4) Uiso 0.50 1 d PD C 2 H33B H -0.0843 0.7321 0.1115 0.133 Uiso 0.50 1 calc PR C 2 C34B C -0.2007(14) 0.7959(12) 0.0854(3) 0.107(4) Uiso 0.50 1 d PD C 2 H34B H -0.2664 0.7714 0.0951 0.129 Uiso 0.50 1 calc PR C 2 C35B C -0.2079(9) 0.8584(9) 0.0611(2) 0.090(3) Uiso 0.50 1 d PD C 2 H35B H -0.2801 0.8831 0.0547 0.108 Uiso 0.50 1 calc PR C 2 C36B C -0.1086(10) 0.8859(10) 0.0458(2) 0.075(3) Uiso 0.50 1 d PD C 2 H36B H -0.1145 0.9228 0.0284 0.090 Uiso 0.50 1 calc PR C 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 0.0341(5) 0.1090(8) 0.0330(4) 0.0105(5) 0.0012(3) -0.0088(5) O1 0.0381(13) 0.0803(18) 0.0351(12) 0.0099(11) -0.0019(10) -0.0076(12) O2 0.0328(13) 0.092(2) 0.0385(12) 0.0121(12) 0.0022(10) -0.0062(12) N1 0.0280(14) 0.0680(19) 0.0321(13) 0.0020(13) 0.0012(11) -0.0049(13) N2 0.0302(14) 0.0460(16) 0.0316(12) 0.0018(11) -0.0007(11) -0.0040(11) C1 0.045(2) 0.141(5) 0.065(3) 0.032(3) 0.014(2) 0.006(3) C2 0.042(2) 0.107(3) 0.0411(19) 0.018(2) 0.0094(16) -0.003(2) C3 0.040(2) 0.054(2) 0.0369(17) 0.0055(15) 0.0031(15) -0.0048(15) C4 0.0341(18) 0.0458(19) 0.0347(16) -0.0012(13) 0.0031(13) -0.0016(14) C5 0.0311(15) 0.0346(16) 0.0253(14) 0.0009(11) 0.0006(11) -0.0020(12) C6 0.0372(18) 0.0335(17) 0.0356(15) -0.0003(13) 0.0000(13) 0.0048(14) C7 0.0429(18) 0.0316(16) 0.0325(16) -0.0001(12) -0.0026(13) -0.0057(13) S3 0.0937(7) 0.0344(5) 0.0314(4) -0.0012(3) -0.0089(4) -0.0060(4) S4 0.0361(5) 0.1354(10) 0.0321(4) 0.0005(5) 0.0011(4) -0.0107(5) O5 0.153(3) 0.0638(17) 0.0349(13) 0.0018(13) -0.0192(16) -0.0368(19) O7 0.0431(14) 0.113(2) 0.0354(12) 0.0067(13) -0.0020(11) -0.0208(14) O8 0.0353(13) 0.0791(17) 0.0373(12) 0.0027(11) 0.0073(10) -0.0078(11) N5 0.095(2) 0.0365(17) 0.0357(15) -0.0001(12) -0.0057(15) -0.0128(16) N6 0.0564(17) 0.0389(15) 0.0283(13) -0.0008(11) -0.0079(12) -0.0096(13) N7 0.0379(16) 0.0632(19) 0.0303(13) 0.0026(13) 0.0014(12) -0.0131(13) N8 0.0337(16) 0.086(2) 0.0322(15) 0.0002(14) -0.0022(12) -0.0130(15) O6A 0.119(9) 0.053(4) 0.036(4) -0.016(3) -0.016(5) -0.019(5) C15A 0.160(18) 0.108(17) 0.087(10) -0.006(13) -0.053(10) -0.027(14) C16A 0.128(11) 0.049(6) 0.036(5) -0.014(4) -0.017(6) -0.002(6) O6B 0.111(9) 0.040(4) 0.037(3) -0.006(3) -0.023(5) -0.021(4) C15B 0.085(7) 0.052(7) 0.048(6) -0.022(5) -0.015(5) 0.001(5) C16B 0.115(11) 0.060(7) 0.044(5) -0.013(5) -0.033(7) 0.004(7) C17 0.130(4) 0.047(2) 0.0366(19) -0.0073(17) -0.006(2) -0.025(2) C18 0.050(2) 0.0343(18) 0.0363(16) -0.0018(13) -0.0035(14) -0.0026(14) C19 0.045(2) 0.0364(18) 0.0258(14) 0.0030(12) -0.0052(13) -0.0048(15) C20 0.0387(18) 0.046(2) 0.0362(16) -0.0046(14) -0.0006(14) 0.0003(16) C21 0.0360(18) 0.053(2) 0.0333(16) 0.0004(15) 0.0021(13) -0.0092(16) C22 0.046(2) 0.0356(18) 0.0403(17) 0.0022(13) -0.0025(15) -0.0084(16) C23 0.0392(19) 0.043(2) 0.0383(16) 0.0012(14) -0.0021(14) 0.0015(15) C24 0.0327(17) 0.0472(19) 0.0298(15) 0.0013(13) -0.0028(12) -0.0073(15) C25 0.0374(19) 0.056(2) 0.0358(16) 0.0017(15) 0.0025(14) -0.0024(16) C26 0.039(2) 0.069(2) 0.0351(17) 0.0008(16) 0.0034(15) -0.0132(16) C27 0.048(2) 0.090(3) 0.0373(18) 0.0091(18) 0.0094(16) -0.0062(19) C28 0.042(2) 0.089(3) 0.054(2) 0.011(2) 0.0111(17) 0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C4 1.668(3) . ? O1 C3 1.208(4) . ? O2 C3 1.329(4) . ? O2 C2 1.467(4) . ? N1 C3 1.373(4) . ? N1 C4 1.383(4) . ? N1 H1N 0.885(18) . ? N2 C4 1.324(4) . ? N2 C5 1.436(4) . ? N2 H2N 0.883(18) . ? C1 C2 1.498(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C5 C6 1.382(4) . ? C5 C5 1.384(6) 6 ? C6 C7 1.386(4) . ? C6 H6 0.9500 . ? C7 C7 1.369(6) 6 ? C7 H7 0.9500 . ? S3 C18 1.662(3) . ? S4 C25 1.672(3) . ? O5 C17 1.200(4) . ? O7 C26 1.204(4) . ? O8 C26 1.322(4) . ? O8 C27 1.461(4) . ? N5 C18 1.376(4) . ? N5 C17 1.378(4) . ? N5 H5N 0.900(19) . ? N6 C18 1.331(4) . ? N6 C19 1.424(4) . ? N6 H6N 0.903(18) . ? N7 C25 1.321(4) . ? N7 C24 1.432(4) . ? N7 H7N 0.925(18) . ? N8 C26 1.377(4) . ? N8 C25 1.384(4) . ? N8 H8N 0.897(18) . ? O6A C17 1.395(10) . ? O6A C16A 1.476(10) . ? C15A C16A 1.454(14) . ? C15A H15A 0.9800 . ? C15A H15B 0.9800 . ? C15A H15C 0.9800 . ? C16A H16A 0.9900 . ? C16A H16B 0.9900 . ? O6B C17 1.348(10) . ? O6B C16B 1.468(11) . ? C15B C16B 1.442(12) . ? C15B H15D 0.9800 . ? C15B H15E 0.9800 . ? C15B H15F 0.9800 . ? C16B H16C 0.9900 . ? C16B H16D 0.9900 . ? C19 C24 1.374(4) . ? C19 C20 1.387(4) . ? C20 C21 1.388(5) . ? C20 H20 0.9500 . ? C21 C22 1.370(5) . ? C21 H21 0.9500 . ? C22 C23 1.393(4) . ? C22 H22 0.9500 . ? C23 C24 1.383(4) . ? C23 H23 0.9500 . ? C27 C28 1.490(5) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C30A C31A 1.464(18) . ? C30A H31A 0.9800 . ? C30A H31B 0.9800 . ? C30A H31C 0.9800 . ? C31A C32A 1.352(13) . ? C31A C36A 1.413(12) . ? C32A C33A 1.410(13) . ? C32A H32A 0.9500 . ? C33A C34A 1.396(14) . ? C33A H33A 0.9500 . ? C34A C35A 1.369(14) . ? C34A H34A 0.9500 . ? C35A C36A 1.425(13) . ? C35A H35A 0.9500 . ? C36A H36A 0.9500 . ? C30B C31B 1.48(2) . ? C30B H30D 0.9800 . ? C30B H30E 0.9800 . ? C30B H30F 0.9800 . ? C31B C32B 1.338(12) . ? C31B C36B 1.407(11) . ? C32B C33B 1.396(13) . ? C32B H32B 0.9500 . ? C33B C34B 1.384(12) . ? C33B H33B 0.9500 . ? C34B C35B 1.391(13) . ? C34B H34B 0.9500 . ? C35B C36B 1.423(12) . ? C35B H35B 0.9500 . ? C36B H36B 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 C3 O2 C2 115.4(2) . . ? C3 N1 C4 126.9(3) . . ? C3 N1 H1N 115(2) . . ? C4 N1 H1N 117(2) . . ? C4 N2 C5 122.6(2) . . ? C4 N2 H2N 117(2) . . ? C5 N2 H2N 120(2) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 C1 106.2(3) . . ? O2 C2 H2A 110.5 . . ? C1 C2 H2A 110.5 . . ? O2 C2 H2B 110.5 . . ? C1 C2 H2B 110.5 . . ? H2A C2 H2B 108.7 . . ? O1 C3 O2 125.0(3) . . ? O1 C3 N1 125.6(3) . . ? O2 C3 N1 109.4(3) . . ? N2 C4 N1 116.9(3) . . ? N2 C4 S1 123.4(2) . . ? N1 C4 S1 119.7(2) . . ? C6 C5 C5 120.02(17) . 6 ? C6 C5 N2 119.7(3) . . ? C5 C5 N2 120.29(16) 6 . ? C5 C6 C7 119.7(3) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C7 C7 C6 120.30(18) 6 . ? C7 C7 H7 119.9 6 . ? C6 C7 H7 119.9 . . ? C26 O8 C27 114.8(3) . . ? C18 N5 C17 127.1(3) . . ? C18 N5 H5N 117(2) . . ? C17 N5 H5N 116(2) . . ? C18 N6 C19 123.7(3) . . ? C18 N6 H6N 117(2) . . ? C19 N6 H6N 119(2) . . ? C25 N7 C24 124.1(3) . . ? C25 N7 H7N 112(2) . . ? C24 N7 H7N 123(2) . . ? C26 N8 C25 126.4(3) . . ? C26 N8 H8N 117(2) . . ? C25 N8 H8N 117(2) . . ? C17 O6A C16A 116.5(9) . . ? C15A C16A O6A 110.9(12) . . ? C15A C16A H16A 109.5 . . ? O6A C16A H16A 109.5 . . ? C15A C16A H16B 109.5 . . ? O6A C16A H16B 109.5 . . ? H16A C16A H16B 108.1 . . ? C17 O6B C16B 115.7(9) . . ? C16B C15B H15D 109.5 . . ? C16B C15B H15E 109.5 . . ? H15D C15B H15E 109.5 . . ? C16B C15B H15F 109.5 . . ? H15D C15B H15F 109.5 . . ? H15E C15B H15F 109.5 . . ? C15B C16B O6B 104.2(10) . . ? C15B C16B H16C 110.9 . . ? O6B C16B H16C 110.9 . . ? C15B C16B H16D 110.9 . . ? O6B C16B H16D 110.9 . . ? H16C C16B H16D 108.9 . . ? O5 C17 O6B 121.2(5) . . ? O5 C17 N5 125.9(3) . . ? O6B C17 N5 111.3(6) . . ? O5 C17 O6A 127.8(6) . . ? O6B C17 O6A 27.4(6) . . ? N5 C17 O6A 104.6(5) . . ? N6 C18 N5 116.5(3) . . ? N6 C18 S3 124.0(2) . . ? N5 C18 S3 119.5(2) . . ? C24 C19 C20 119.9(3) . . ? C24 C19 N6 121.4(3) . . ? C20 C19 N6 118.6(3) . . ? C19 C20 C21 120.0(3) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C22 C21 C20 120.1(3) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C22 C23 120.0(3) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C24 C23 C22 119.8(3) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C19 C24 C23 120.3(3) . . ? C19 C24 N7 121.2(3) . . ? C23 C24 N7 118.4(3) . . ? N7 C25 N8 117.1(3) . . ? N7 C25 S4 123.7(3) . . ? N8 C25 S4 119.2(2) . . ? O7 C26 O8 125.5(3) . . ? O7 C26 N8 125.0(3) . . ? O8 C26 N8 109.5(3) . . ? O8 C27 C28 106.5(3) . . ? O8 C27 H27A 110.4 . . ? C28 C27 H27A 110.4 . . ? O8 C27 H27B 110.4 . . ? C28 C27 H27B 110.4 . . ? H27A C27 H27B 108.6 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C32A C31A C36A 115.4(14) . . ? C32A C31A C30A 114.6(15) . . ? C36A C31A C30A 129.5(16) . . ? C31A C32A C33A 117.8(14) . . ? C31A C32A H32A 121.1 . . ? C33A C32A H32A 121.1 . . ? C34A C33A C32A 132.1(15) . . ? C34A C33A H33A 114.0 . . ? C32A C33A H33A 114.0 . . ? C35A C34A C33A 106.2(19) . . ? C35A C34A H34A 126.9 . . ? C33A C34A H34A 126.9 . . ? C34A C35A C36A 126.2(18) . . ? C34A C35A H35A 116.9 . . ? C36A C35A H35A 116.9 . . ? C31A C36A C35A 121.6(14) . . ? C31A C36A H36A 119.2 . . ? C35A C36A H36A 119.2 . . ? C31B C30B H30D 109.5 . . ? C31B C30B H30E 109.5 . . ? H30D C30B H30E 109.5 . . ? C31B C30B H30F 109.5 . . ? H30D C30B H30F 109.5 . . ? H30E C30B H30F 109.5 . . ? C32B C31B C36B 121.1(12) . . ? C32B C31B C30B 108.4(15) . . ? C36B C31B C30B 129.9(15) . . ? C31B C32B C33B 118.5(13) . . ? C31B C32B H32B 120.8 . . ? C33B C32B H32B 120.8 . . ? C34B C33B C32B 124.6(13) . . ? C34B C33B H33B 117.7 . . ? C32B C33B H33B 117.7 . . ? C33B C34B C35B 115.9(14) . . ? C33B C34B H34B 122.1 . . ? C35B C34B H34B 122.1 . . ? C34B C35B C36B 120.9(12) . . ? C34B C35B H35B 119.5 . . ? C36B C35B H35B 119.5 . . ? C31B C36B C35B 118.8(10) . . ? C31B C36B H36B 120.6 . . ? C35B C36B H36B 120.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 O2 C2 C1 -174.8(4) . . . . ? C2 O2 C3 O1 -1.7(5) . . . . ? C2 O2 C3 N1 178.0(3) . . . . ? C4 N1 C3 O1 8.5(6) . . . . ? C4 N1 C3 O2 -171.3(3) . . . . ? C5 N2 C4 N1 175.8(3) . . . . ? C5 N2 C4 S1 -4.0(4) . . . . ? C3 N1 C4 N2 -5.5(5) . . . . ? C3 N1 C4 S1 174.3(3) . . . . ? C4 N2 C5 C6 -95.9(4) . . . . ? C4 N2 C5 C5 86.0(4) . . . 6 ? C5 C5 C6 C7 0.0(5) 6 . . . ? N2 C5 C6 C7 -178.2(2) . . . . ? C5 C6 C7 C7 0.2(5) . . . 6 ? C17 O6A C16A C15A -86.7(14) . . . . ? C17 O6B C16B C15B -176.0(10) . . . . ? C16B O6B C17 O5 8.2(13) . . . . ? C16B O6B C17 N5 174.8(9) . . . . ? C16B O6B C17 O6A -105(2) . . . . ? C18 N5 C17 O5 -4.0(8) . . . . ? C18 N5 C17 O6B -169.8(6) . . . . ? C18 N5 C17 O6A 162.2(6) . . . . ? C16A O6A C17 O5 -18.9(14) . . . . ? C16A O6A C17 O6B 67.0(17) . . . . ? C16A O6A C17 N5 175.2(8) . . . . ? C19 N6 C18 N5 -174.2(3) . . . . ? C19 N6 C18 S3 6.1(5) . . . . ? C17 N5 C18 N6 4.8(6) . . . . ? C17 N5 C18 S3 -175.5(4) . . . . ? C18 N6 C19 C24 -94.5(4) . . . . ? C18 N6 C19 C20 88.5(4) . . . . ? C24 C19 C20 C21 -0.1(4) . . . . ? N6 C19 C20 C21 176.9(3) . . . . ? C19 C20 C21 C22 0.4(5) . . . . ? C20 C21 C22 C23 -0.4(4) . . . . ? C21 C22 C23 C24 0.0(4) . . . . ? C20 C19 C24 C23 -0.3(4) . . . . ? N6 C19 C24 C23 -177.2(3) . . . . ? C20 C19 C24 N7 -176.3(3) . . . . ? N6 C19 C24 N7 6.7(4) . . . . ? C22 C23 C24 C19 0.4(4) . . . . ? C22 C23 C24 N7 176.5(3) . . . . ? C25 N7 C24 C19 -88.5(4) . . . . ? C25 N7 C24 C23 95.4(4) . . . . ? C24 N7 C25 N8 -170.6(3) . . . . ? C24 N7 C25 S4 10.1(5) . . . . ? C26 N8 C25 N7 -1.1(6) . . . . ? C26 N8 C25 S4 178.2(3) . . . . ? C27 O8 C26 O7 -3.7(6) . . . . ? C27 O8 C26 N8 176.8(3) . . . . ? C25 N8 C26 O7 -6.5(6) . . . . ? C25 N8 C26 O8 173.1(3) . . . . ? C26 O8 C27 C28 178.2(3) . . . . ? C36A C31A C32A C33A -2(2) . . . . ? C30A C31A C32A C33A -174.4(13) . . . . ? C31A C32A C33A C34A 4(2) . . . . ? C32A C33A C34A C35A -7(3) . . . . ? C33A C34A C35A C36A 9(3) . . . . ? C32A C31A C36A C35A 4(2) . . . . ? C30A C31A C36A C35A 175.4(16) . . . . ? C34A C35A C36A C31A -9(3) . . . . ? C36B C31B C32B C33B -0.9(18) . . . . ? C30B C31B C32B C33B -173.0(15) . . . . ? C31B C32B C33B C34B 1(2) . . . . ? C32B C33B C34B C35B -3(2) . . . . ? C33B C34B C35B C36B 5.3(18) . . . . ? C32B C31B C36B C35B 3.2(16) . . . . ? C30B C31B C36B C35B 173.5(17) . . . . ? C34B C35B C36B C31B -5.6(16) . . . . ? 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 H1N S3 0.885(18) 2.442(19) 3.322(3) 173(3) 6_655 N2 H2N O1 0.883(18) 1.97(3) 2.674(3) 136(3) . N5 H5N S1 0.900(19) 2.37(2) 3.255(3) 170(3) 6_545 N6 H6N O5 0.903(18) 1.95(3) 2.670(3) 136(3) . N7 H7N O7 0.925(18) 1.86(3) 2.651(3) 142(3) . N8 H8N S4 0.897(18) 2.44(2) 3.325(3) 168(3) 7 _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 66.89 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.274 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.041 data_TE-formIII _database_code_depnum_ccdc_archive 'CCDC 808872' #TrackingRef '- TE_structures2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 N4 O4 S2' _chemical_formula_sum 'C14 H18 N4 O4 S2' _chemical_formula_weight 370.44 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.7333(5) _cell_length_b 11.8079(7) _cell_length_c 16.2174(12) _cell_angle_alpha 95.293(3) _cell_angle_beta 100.405(4) _cell_angle_gamma 113.044(4) _cell_volume 1829.85(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 2.868 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6263 _exptl_absorpt_correction_T_max 0.8030 _exptl_absorpt_process_details ; Denzo (Otwinowski, Borek, Majewski & Minor,2003) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8675 _diffrn_reflns_av_R_equivalents 0.1113 _diffrn_reflns_av_sigmaI/netI 0.0824 _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 -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.14 _diffrn_reflns_theta_max 66.76 _reflns_number_total 6132 _reflns_number_gt 4201 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0697P)^2^+1.7518P] 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 6132 _refine_ls_number_parameters 461 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0963 _refine_ls_R_factor_gt 0.0603 _refine_ls_wR_factor_ref 0.1633 _refine_ls_wR_factor_gt 0.1413 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.58794(10) 0.74122(9) 0.33336(7) 0.0345(3) Uani 1 1 d . . . S2 S 0.08044(10) 0.69273(10) 0.06405(7) 0.0350(3) Uani 1 1 d . . . S3 S 0.59467(11) 0.39289(10) 0.36743(8) 0.0448(3) Uani 1 1 d . . . S4 S 0.97152(11) 0.29086(13) 0.20458(8) 0.0516(4) Uani 1 1 d . . . O1 O 0.1844(3) 0.5051(2) 0.40425(18) 0.0344(7) Uani 1 1 d . . . O2 O 0.2882(3) 0.3721(2) 0.41772(19) 0.0378(7) Uani 1 1 d . . . O3 O 0.3278(3) 0.4910(3) 0.19094(19) 0.0477(8) Uani 1 1 d . . . O4 O 0.2007(3) 0.3430(2) 0.07501(17) 0.0358(7) Uani 1 1 d . . . O5 O 1.0077(3) 0.6415(3) 0.30954(19) 0.0393(7) Uani 1 1 d . . . O6 O 0.8902(3) 0.7610(2) 0.2809(2) 0.0391(7) Uani 1 1 d . . . O7 O 0.5050(3) 0.1569(4) 0.0916(2) 0.0581(10) Uani 1 1 d . . . O8 O 0.5817(3) 0.2060(4) -0.02648(19) 0.0590(10) Uani 1 1 d . . . N1 N 0.4089(3) 0.5580(3) 0.3894(2) 0.0314(8) Uani 1 1 d . . . H1N H 0.464(4) 0.526(4) 0.387(3) 0.038 Uiso 1 1 d . . . N2 N 0.3404(3) 0.7143(3) 0.3574(2) 0.0276(7) Uani 1 1 d . . . H2N H 0.270(4) 0.677(4) 0.379(3) 0.033 Uiso 1 1 d . . . N3 N 0.2931(3) 0.7010(3) 0.1835(2) 0.0321(8) Uani 1 1 d . . . H3N H 0.330(4) 0.663(4) 0.204(3) 0.039 Uiso 1 1 d . . . N4 N 0.1806(4) 0.5225(3) 0.0827(2) 0.0339(8) Uani 1 1 d . . . H4N H 0.113(4) 0.481(4) 0.042(3) 0.041 Uiso 1 1 d . . . N5 N 0.7817(4) 0.5826(3) 0.3212(2) 0.0378(9) Uani 1 1 d . . . H5N H 0.711(5) 0.603(4) 0.315(3) 0.045 Uiso 1 1 d . . . N6 N 0.8465(3) 0.4235(3) 0.3507(2) 0.0330(8) Uani 1 1 d . . . H6N H 0.929(5) 0.471(4) 0.342(3) 0.040 Uiso 1 1 d . . . N7 N 0.7144(4) 0.1990(3) 0.2265(2) 0.0338(8) Uani 1 1 d . . . H7N H 0.629(5) 0.177(4) 0.206(3) 0.041 Uiso 1 1 d . . . N8 N 0.7367(4) 0.2335(4) 0.0910(2) 0.0447(10) Uani 1 1 d . . . H8N H 0.797(5) 0.265(5) 0.063(3) 0.054 Uiso 1 1 d . . . C1 C 0.1824(5) 0.1623(4) 0.4373(3) 0.0515(13) Uani 1 1 d . . . H1A H 0.1964 0.1352 0.3820 0.077 Uiso 1 1 calc R . . H1B H 0.0996 0.0972 0.4482 0.077 Uiso 1 1 calc R . . H1C H 0.2642 0.1767 0.4823 0.077 Uiso 1 1 calc R . . C2 C 0.1630(4) 0.2803(4) 0.4362(3) 0.0408(11) Uani 1 1 d . . . H2A H 0.0795 0.2667 0.3917 0.049 Uiso 1 1 calc R . . H2B H 0.1509 0.3098 0.4921 0.049 Uiso 1 1 calc R . . C3 C 0.2825(4) 0.4804(4) 0.4042(3) 0.0318(9) Uani 1 1 d . . . C4 C 0.4378(4) 0.6696(4) 0.3618(2) 0.0291(9) Uani 1 1 d . . . C5 C 0.3539(4) 0.8253(3) 0.3227(2) 0.0271(9) Uani 1 1 d . . . C6 C 0.3920(4) 0.9368(4) 0.3764(3) 0.0298(9) Uani 1 1 d . . . H6 H 0.4099 0.9407 0.4364 0.036 Uiso 1 1 calc R . . C7 C 0.4041(4) 1.0430(4) 0.3430(3) 0.0345(9) Uani 1 1 d . . . H7 H 0.4306 1.1200 0.3800 0.041 Uiso 1 1 calc R . . C8 C 0.3774(4) 1.0372(4) 0.2554(3) 0.0359(10) Uani 1 1 d . . . H8 H 0.3851 1.1103 0.2325 0.043 Uiso 1 1 calc R . . C9 C 0.3394(4) 0.9251(4) 0.2011(3) 0.0330(9) Uani 1 1 d . . . H9 H 0.3231 0.9217 0.1412 0.040 Uiso 1 1 calc R . . C10 C 0.3254(4) 0.8174(3) 0.2349(2) 0.0278(9) Uani 1 1 d . . . C11 C 0.1918(4) 0.6401(4) 0.1144(2) 0.0294(9) Uani 1 1 d . . . C12 C 0.2438(4) 0.4541(4) 0.1230(3) 0.0343(9) Uani 1 1 d . . . C13 C 0.2441(5) 0.2540(4) 0.1147(3) 0.0407(10) Uani 1 1 d . . . H13A H 0.2303 0.2544 0.1735 0.049 Uiso 1 1 calc R . . H13B H 0.3437 0.2757 0.1170 0.049 Uiso 1 1 calc R . . C14 C 0.1552(5) 0.1289(4) 0.0606(3) 0.0508(12) Uani 1 1 d . . . H14A H 0.0572 0.1077 0.0602 0.076 Uiso 1 1 calc R . . H14B H 0.1822 0.0657 0.0836 0.076 Uiso 1 1 calc R . . H14C H 0.1676 0.1308 0.0022 0.076 Uiso 1 1 calc R . . C15 C 0.9688(5) 0.9517(4) 0.2286(3) 0.0548(14) Uani 1 1 d . . . H15A H 0.8958 0.9143 0.1757 0.082 Uiso 1 1 calc R . . H15B H 1.0496 1.0193 0.2177 0.082 Uiso 1 1 calc R . . H15C H 0.9332 0.9855 0.2717 0.082 Uiso 1 1 calc R . . C16 C 1.0111(4) 0.8545(4) 0.2600(3) 0.0377(10) Uani 1 1 d . . . H16A H 1.0413 0.8155 0.2154 0.045 Uiso 1 1 calc R . . H16B H 1.0895 0.8924 0.3111 0.045 Uiso 1 1 calc R . . C17 C 0.9049(4) 0.6607(4) 0.3042(3) 0.0319(9) Uani 1 1 d . . . C18 C 0.7491(4) 0.4671(4) 0.3455(3) 0.0333(9) Uani 1 1 d . . . C19 C 0.8231(4) 0.3042(3) 0.3752(3) 0.0294(9) Uani 1 1 d . . . C20 C 0.8622(4) 0.2985(4) 0.4600(3) 0.0341(9) Uani 1 1 d . . . H20 H 0.9052 0.3731 0.5016 0.041 Uiso 1 1 calc R . . C21 C 0.8385(4) 0.1828(4) 0.4846(3) 0.0373(10) Uani 1 1 d . . . H21 H 0.8654 0.1785 0.5429 0.045 Uiso 1 1 calc R . . C22 C 0.7763(4) 0.0756(4) 0.4242(3) 0.0347(10) Uani 1 1 d . . . H22 H 0.7603 -0.0029 0.4410 0.042 Uiso 1 1 calc R . . C23 C 0.7367(4) 0.0807(4) 0.3392(3) 0.0333(9) Uani 1 1 d . . . H23 H 0.6930 0.0060 0.2978 0.040 Uiso 1 1 calc R . . C24 C 0.7611(4) 0.1954(4) 0.3145(3) 0.0296(9) Uani 1 1 d . . . C25 C 0.7989(4) 0.2375(4) 0.1750(3) 0.0362(10) Uani 1 1 d . . . C26 C 0.5977(5) 0.1948(5) 0.0549(3) 0.0459(12) Uani 1 1 d . . . C27 C 0.4413(5) 0.1771(6) -0.0748(3) 0.0667(17) Uani 1 1 d . . . H27A H 0.3722 0.1168 -0.0492 0.080 Uiso 1 1 calc R . . H27B H 0.4283 0.1382 -0.1342 0.080 Uiso 1 1 calc R . . C28 C 0.4188(6) 0.2930(7) -0.0741(4) 0.087(2) Uani 1 1 d . . . H28A H 0.4211 0.3260 -0.0159 0.131 Uiso 1 1 calc R . . H28B H 0.3279 0.2745 -0.1114 0.131 Uiso 1 1 calc R . . H28C H 0.4924 0.3553 -0.0946 0.131 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 S1 0.0285(5) 0.0273(5) 0.0490(7) 0.0111(5) 0.0109(4) 0.0112(4) S2 0.0370(5) 0.0330(6) 0.0337(6) 0.0039(4) 0.0029(4) 0.0160(5) S3 0.0357(6) 0.0301(6) 0.0794(9) 0.0228(6) 0.0261(5) 0.0165(5) S4 0.0349(6) 0.0833(9) 0.0406(7) 0.0229(6) 0.0150(5) 0.0236(6) O1 0.0340(15) 0.0319(15) 0.0443(18) 0.0112(13) 0.0154(13) 0.0174(13) O2 0.0378(15) 0.0299(15) 0.0551(19) 0.0185(14) 0.0212(13) 0.0171(13) O3 0.0569(19) 0.0355(17) 0.0417(19) -0.0008(14) -0.0115(16) 0.0217(15) O4 0.0444(16) 0.0279(15) 0.0335(16) -0.0010(13) 0.0039(13) 0.0169(13) O5 0.0331(15) 0.0342(16) 0.058(2) 0.0164(14) 0.0167(13) 0.0177(13) O6 0.0345(15) 0.0292(15) 0.062(2) 0.0216(14) 0.0204(13) 0.0151(13) O7 0.0412(18) 0.088(3) 0.044(2) 0.0259(19) 0.0131(15) 0.0218(18) O8 0.0411(18) 0.097(3) 0.0355(19) 0.0228(19) 0.0078(14) 0.0239(18) N1 0.0309(18) 0.0270(18) 0.038(2) 0.0124(15) 0.0091(15) 0.0122(15) N2 0.0286(17) 0.0260(17) 0.0324(19) 0.0105(15) 0.0098(14) 0.0133(14) N3 0.038(2) 0.0260(18) 0.031(2) 0.0041(15) 0.0025(16) 0.0151(15) N4 0.0378(19) 0.0286(19) 0.032(2) 0.0002(15) -0.0029(15) 0.0161(16) N5 0.0317(18) 0.0303(19) 0.060(3) 0.0201(17) 0.0169(17) 0.0162(16) N6 0.0299(18) 0.0241(18) 0.048(2) 0.0121(16) 0.0126(16) 0.0113(15) N7 0.0291(17) 0.040(2) 0.031(2) 0.0116(16) 0.0079(15) 0.0116(16) N8 0.035(2) 0.069(3) 0.036(2) 0.022(2) 0.0162(16) 0.0209(19) C1 0.049(3) 0.031(2) 0.072(4) 0.017(2) 0.007(2) 0.016(2) C2 0.039(2) 0.033(2) 0.054(3) 0.016(2) 0.022(2) 0.012(2) C3 0.036(2) 0.028(2) 0.032(2) 0.0063(18) 0.0096(18) 0.0125(18) C4 0.031(2) 0.029(2) 0.026(2) 0.0057(17) 0.0052(16) 0.0113(17) C5 0.0207(18) 0.026(2) 0.034(2) 0.0092(17) 0.0071(16) 0.0082(16) C6 0.028(2) 0.029(2) 0.031(2) 0.0031(17) 0.0085(16) 0.0110(17) C7 0.034(2) 0.024(2) 0.043(3) -0.0007(18) 0.0106(18) 0.0106(18) C8 0.030(2) 0.026(2) 0.052(3) 0.013(2) 0.0105(19) 0.0108(18) C9 0.034(2) 0.027(2) 0.034(2) 0.0088(18) 0.0040(17) 0.0104(18) C10 0.0245(19) 0.023(2) 0.033(2) 0.0039(17) 0.0041(16) 0.0084(16) C11 0.032(2) 0.029(2) 0.027(2) 0.0069(17) 0.0079(17) 0.0119(17) C12 0.036(2) 0.030(2) 0.035(2) 0.0031(19) 0.0096(19) 0.0127(19) C13 0.047(3) 0.033(2) 0.045(3) 0.003(2) 0.007(2) 0.021(2) C14 0.063(3) 0.034(3) 0.051(3) 0.002(2) 0.009(2) 0.019(2) C15 0.055(3) 0.047(3) 0.066(3) 0.032(3) 0.018(2) 0.018(2) C16 0.037(2) 0.030(2) 0.048(3) 0.016(2) 0.021(2) 0.0103(19) C17 0.029(2) 0.026(2) 0.040(2) 0.0077(18) 0.0090(18) 0.0091(18) C18 0.033(2) 0.027(2) 0.043(3) 0.0103(19) 0.0099(18) 0.0139(18) C19 0.028(2) 0.026(2) 0.042(2) 0.0150(18) 0.0145(17) 0.0143(17) C20 0.032(2) 0.030(2) 0.038(2) 0.0040(19) 0.0114(18) 0.0112(18) C21 0.040(2) 0.043(3) 0.030(2) 0.013(2) 0.0102(18) 0.016(2) C22 0.040(2) 0.031(2) 0.041(3) 0.016(2) 0.0157(19) 0.0181(19) C23 0.035(2) 0.027(2) 0.039(2) 0.0070(18) 0.0102(18) 0.0128(18) C24 0.028(2) 0.029(2) 0.034(2) 0.0094(18) 0.0116(17) 0.0105(17) C25 0.038(2) 0.040(2) 0.036(2) 0.012(2) 0.0121(19) 0.019(2) C26 0.039(3) 0.062(3) 0.038(3) 0.017(2) 0.011(2) 0.020(2) C27 0.037(3) 0.109(5) 0.047(3) 0.021(3) 0.000(2) 0.025(3) C28 0.061(4) 0.131(6) 0.079(5) 0.045(4) 0.023(3) 0.041(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 C4 1.673(4) . ? S2 C11 1.674(4) . ? S3 C18 1.666(4) . ? S4 C25 1.664(4) . ? O1 C3 1.197(5) . ? O2 C3 1.340(5) . ? O2 C2 1.461(5) . ? O3 C12 1.209(5) . ? O4 C12 1.321(5) . ? O4 C13 1.462(5) . ? O5 C17 1.201(5) . ? O6 C17 1.333(4) . ? O6 C16 1.458(4) . ? O7 C26 1.208(5) . ? O8 C26 1.325(5) . ? O8 C27 1.457(5) . ? N1 C4 1.368(5) . ? N1 C3 1.387(5) . ? N1 H1N 0.82(4) . ? N2 C4 1.339(5) . ? N2 C5 1.439(5) . ? N2 H2N 0.86(4) . ? N3 C11 1.325(5) . ? N3 C10 1.420(5) . ? N3 H3N 0.77(4) . ? N4 C12 1.381(5) . ? N4 C11 1.386(5) . ? N4 H4N 0.83(4) . ? N5 C17 1.378(5) . ? N5 C18 1.384(5) . ? N5 H5N 0.88(5) . ? N6 C18 1.327(5) . ? N6 C19 1.438(5) . ? N6 H6N 0.88(4) . ? N7 C25 1.323(5) . ? N7 C24 1.436(5) . ? N7 H7N 0.84(4) . ? N8 C26 1.371(6) . ? N8 C25 1.392(5) . ? N8 H8N 0.85(5) . ? C1 C2 1.489(6) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C5 C6 1.377(5) . ? C5 C10 1.388(5) . ? C6 C7 1.380(5) . ? C6 H6 0.9500 . ? C7 C8 1.387(6) . ? C7 H7 0.9500 . ? C8 C9 1.388(6) . ? C8 H8 0.9500 . ? C9 C10 1.396(5) . ? C9 H9 0.9500 . ? C13 C14 1.490(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.488(6) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C19 C20 1.380(6) . ? C19 C24 1.386(6) . ? C20 C21 1.398(6) . ? C20 H20 0.9500 . ? C21 C22 1.372(6) . ? C21 H21 0.9500 . ? C22 C23 1.382(6) . ? C22 H22 0.9500 . ? C23 C24 1.386(5) . ? C23 H23 0.9500 . ? C27 C28 1.480(9) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 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 C3 O2 C2 115.1(3) . . ? C12 O4 C13 115.5(3) . . ? C17 O6 C16 116.0(3) . . ? C26 O8 C27 117.3(4) . . ? C4 N1 C3 125.9(3) . . ? C4 N1 H1N 117(3) . . ? C3 N1 H1N 115(3) . . ? C4 N2 C5 121.9(3) . . ? C4 N2 H2N 118(3) . . ? C5 N2 H2N 120(3) . . ? C11 N3 C10 129.1(3) . . ? C11 N3 H3N 116(3) . . ? C10 N3 H3N 114(3) . . ? C12 N4 C11 127.2(3) . . ? C12 N4 H4N 114(3) . . ? C11 N4 H4N 116(3) . . ? C17 N5 C18 128.0(4) . . ? C17 N5 H5N 120(3) . . ? C18 N5 H5N 112(3) . . ? C18 N6 C19 120.9(3) . . ? C18 N6 H6N 119(3) . . ? C19 N6 H6N 119(3) . . ? C25 N7 C24 123.6(3) . . ? C25 N7 H7N 117(3) . . ? C24 N7 H7N 120(3) . . ? C26 N8 C25 127.8(4) . . ? C26 N8 H8N 121(3) . . ? C25 N8 H8N 111(3) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 C1 106.7(3) . . ? O2 C2 H2A 110.4 . . ? C1 C2 H2A 110.4 . . ? O2 C2 H2B 110.4 . . ? C1 C2 H2B 110.4 . . ? H2A C2 H2B 108.6 . . ? O1 C3 O2 125.7(4) . . ? O1 C3 N1 126.1(4) . . ? O2 C3 N1 108.2(3) . . ? N2 C4 N1 117.0(3) . . ? N2 C4 S1 123.3(3) . . ? N1 C4 S1 119.7(3) . . ? C6 C5 C10 120.9(3) . . ? C6 C5 N2 120.1(3) . . ? C10 C5 N2 119.0(3) . . ? C5 C6 C7 119.9(4) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C6 C7 C8 120.0(4) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C7 C8 C9 120.2(4) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C8 C9 C10 119.7(4) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C5 C10 C9 119.2(4) . . ? C5 C10 N3 117.9(3) . . ? C9 C10 N3 122.8(4) . . ? N3 C11 N4 115.1(3) . . ? N3 C11 S2 126.0(3) . . ? N4 C11 S2 119.0(3) . . ? O3 C12 O4 125.2(4) . . ? O3 C12 N4 125.2(4) . . ? O4 C12 N4 109.5(3) . . ? O4 C13 C14 106.2(3) . . ? O4 C13 H13A 110.5 . . ? C14 C13 H13A 110.5 . . ? O4 C13 H13B 110.5 . . ? C14 C13 H13B 110.5 . . ? H13A C13 H13B 108.7 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C16 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O6 C16 C15 107.3(3) . . ? O6 C16 H16A 110.3 . . ? C15 C16 H16A 110.3 . . ? O6 C16 H16B 110.3 . . ? C15 C16 H16B 110.3 . . ? H16A C16 H16B 108.5 . . ? O5 C17 O6 126.0(4) . . ? O5 C17 N5 125.8(4) . . ? O6 C17 N5 108.3(3) . . ? N6 C18 N5 116.5(3) . . ? N6 C18 S3 124.3(3) . . ? N5 C18 S3 119.2(3) . . ? C20 C19 C24 120.0(3) . . ? C20 C19 N6 119.4(4) . . ? C24 C19 N6 120.7(3) . . ? C19 C20 C21 119.8(4) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C22 C21 C20 119.7(4) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C21 C22 C23 120.7(4) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C22 C23 C24 119.7(4) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C23 C24 C19 120.1(4) . . ? C23 C24 N7 119.2(4) . . ? C19 C24 N7 120.6(3) . . ? N7 C25 N8 116.5(4) . . ? N7 C25 S4 124.4(3) . . ? N8 C25 S4 119.1(3) . . ? O7 C26 O8 125.7(4) . . ? O7 C26 N8 125.3(4) . . ? O8 C26 N8 109.0(4) . . ? O8 C27 C28 109.8(5) . . ? O8 C27 H27A 109.7 . . ? C28 C27 H27A 109.7 . . ? O8 C27 H27B 109.7 . . ? C28 C27 H27B 109.7 . . ? H27A C27 H27B 108.2 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 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 C3 O2 C2 C1 172.4(4) . . . . ? C2 O2 C3 O1 -1.7(6) . . . . ? C2 O2 C3 N1 178.8(3) . . . . ? C4 N1 C3 O1 -8.9(7) . . . . ? C4 N1 C3 O2 170.7(4) . . . . ? C5 N2 C4 N1 -174.8(3) . . . . ? C5 N2 C4 S1 3.7(5) . . . . ? C3 N1 C4 N2 7.6(6) . . . . ? C3 N1 C4 S1 -170.9(3) . . . . ? C4 N2 C5 C6 -103.2(5) . . . . ? C4 N2 C5 C10 78.2(5) . . . . ? C10 C5 C6 C7 -0.9(6) . . . . ? N2 C5 C6 C7 -179.6(3) . . . . ? C5 C6 C7 C8 0.2(6) . . . . ? C6 C7 C8 C9 -0.5(6) . . . . ? C7 C8 C9 C10 1.3(6) . . . . ? C6 C5 C10 C9 1.8(5) . . . . ? N2 C5 C10 C9 -179.5(3) . . . . ? C6 C5 C10 N3 177.1(3) . . . . ? N2 C5 C10 N3 -4.2(5) . . . . ? C8 C9 C10 C5 -2.0(6) . . . . ? C8 C9 C10 N3 -177.1(3) . . . . ? C11 N3 C10 C5 134.4(4) . . . . ? C11 N3 C10 C9 -50.4(6) . . . . ? C10 N3 C11 N4 -174.7(4) . . . . ? C10 N3 C11 S2 5.5(6) . . . . ? C12 N4 C11 N3 13.2(6) . . . . ? C12 N4 C11 S2 -167.0(3) . . . . ? C13 O4 C12 O3 9.5(6) . . . . ? C13 O4 C12 N4 -171.9(3) . . . . ? C11 N4 C12 O3 -5.7(7) . . . . ? C11 N4 C12 O4 175.8(4) . . . . ? C12 O4 C13 C14 165.1(4) . . . . ? C17 O6 C16 C15 175.0(4) . . . . ? C16 O6 C17 O5 0.3(6) . . . . ? C16 O6 C17 N5 -179.8(3) . . . . ? C18 N5 C17 O5 -1.7(8) . . . . ? C18 N5 C17 O6 178.5(4) . . . . ? C19 N6 C18 N5 -179.8(4) . . . . ? C19 N6 C18 S3 1.0(6) . . . . ? C17 N5 C18 N6 -2.3(7) . . . . ? C17 N5 C18 S3 176.9(4) . . . . ? C18 N6 C19 C20 -91.6(5) . . . . ? C18 N6 C19 C24 88.0(5) . . . . ? C24 C19 C20 C21 -0.3(6) . . . . ? N6 C19 C20 C21 179.3(4) . . . . ? C19 C20 C21 C22 -0.1(6) . . . . ? C20 C21 C22 C23 0.0(6) . . . . ? C21 C22 C23 C24 0.5(6) . . . . ? C22 C23 C24 C19 -1.0(6) . . . . ? C22 C23 C24 N7 -177.4(4) . . . . ? C20 C19 C24 C23 0.9(6) . . . . ? N6 C19 C24 C23 -178.7(4) . . . . ? C20 C19 C24 N7 177.3(3) . . . . ? N6 C19 C24 N7 -2.3(5) . . . . ? C25 N7 C24 C23 -107.0(5) . . . . ? C25 N7 C24 C19 76.5(5) . . . . ? C24 N7 C25 N8 179.0(4) . . . . ? C24 N7 C25 S4 -1.8(6) . . . . ? C26 N8 C25 N7 0.3(7) . . . . ? C26 N8 C25 S4 -179.0(4) . . . . ? C27 O8 C26 O7 3.8(8) . . . . ? C27 O8 C26 N8 -176.1(5) . . . . ? C25 N8 C26 O7 -0.1(9) . . . . ? C25 N8 C26 O8 179.7(4) . . . . ? C26 O8 C27 C28 94.1(6) . . . . ? 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 H1N S3 0.82(4) 2.52(4) 3.327(4) 169(4) . N2 H2N O1 0.86(4) 1.99(4) 2.655(4) 133(4) . N3 H3N O3 0.77(4) 2.01(4) 2.658(4) 142(4) . N3 H3N S1 0.77(4) 2.91(4) 3.461(3) 131(4) . N4 H4N S2 0.83(4) 2.49(4) 3.298(4) 164(4) 2_565 N5 H5N S1 0.88(5) 2.49(5) 3.316(4) 156(4) . N6 H6N O5 0.88(4) 2.02(4) 2.704(4) 133(4) . N6 H6N O1 0.88(4) 2.60(4) 3.288(4) 136(3) 1_655 N7 H7N O7 0.84(4) 2.01(4) 2.689(4) 138(4) . N8 H8N S2 0.85(5) 2.62(5) 3.432(4) 161(4) 2_665 _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 66.76 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.300 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.075 data_TE-DCM _database_code_depnum_ccdc_archive 'CCDC 808874' #TrackingRef '- TE_structures2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 N4 O4 S2, C H2 Cl2' _chemical_formula_sum 'C15 H20 Cl2 N4 O4 S2' _chemical_formula_weight 455.37 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' Cl Cl 0.3639 0.7018 '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 16.1404(3) _cell_length_b 17.3754(3) _cell_length_c 8.2332(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.996(3) _cell_angle_gamma 90.00 _cell_volume 2155.66(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 4.767 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4203 _exptl_absorpt_correction_T_max 0.6471 _exptl_absorpt_process_details ; Denzo (Otwinowski, Borek, Majewski & Minor,2003) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2757 _diffrn_reflns_av_R_equivalents 0.0605 _diffrn_reflns_av_sigmaI/netI 0.0571 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.88 _diffrn_reflns_theta_max 66.94 _reflns_number_total 1781 _reflns_number_gt 1461 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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. The N-H hydrogen atoms found in the electron density map were restrained to a distance of 0.91 \%A to give the best fit to the X-ray data and to ensure stable refinement ; _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^)+(0.1124P)^2^+85.0469P] 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 1781 _refine_ls_number_parameters 143 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1739 _refine_ls_R_factor_gt 0.1591 _refine_ls_wR_factor_ref 0.4220 _refine_ls_wR_factor_gt 0.4149 _refine_ls_goodness_of_fit_ref 1.172 _refine_ls_restrained_S_all 1.171 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.1880(3) 0.8558(2) 1.0073(4) 0.0615(13) Uani 1 1 d . . . O1 O 0.0723(8) 0.7619(6) 0.4539(13) 0.082(4) Uani 1 1 d . . . O2 O 0.1807(6) 0.6736(5) 0.5579(11) 0.044(2) Uani 1 1 d . . . N1 N 0.1660(6) 0.7640(5) 0.7380(11) 0.034(2) Uani 1 1 d D . . H1N H 0.214(5) 0.737(6) 0.805(14) 0.041 Uiso 1 1 d D . . N2 N 0.0714(7) 0.8669(5) 0.6869(13) 0.044(3) Uani 1 1 d D . . H2N H 0.050(9) 0.851(8) 0.573(6) 0.052 Uiso 1 1 d D . . C1 C 0.2167(11) 0.5711(8) 0.407(2) 0.066(4) Uani 1 1 d . . . H1A H 0.2751 0.5896 0.4131 0.099 Uiso 1 1 calc R . . H1B H 0.1917 0.5378 0.3049 0.099 Uiso 1 1 calc R . . H1C H 0.2228 0.5419 0.5124 0.099 Uiso 1 1 calc R . . C2 C 0.1556(10) 0.6391(8) 0.3915(18) 0.054(4) Uani 1 1 d . . . H2A H 0.1615 0.6766 0.3056 0.065 Uiso 1 1 calc R . . H2B H 0.0931 0.6217 0.3528 0.065 Uiso 1 1 calc R . . C3 C 0.1354(10) 0.7368(7) 0.5738(17) 0.050(3) Uani 1 1 d . . . C4 C 0.1365(8) 0.8275(7) 0.7959(16) 0.041(3) Uani 1 1 d . . . C5 C 0.0365(7) 0.9389(6) 0.7240(14) 0.035(3) Uani 1 1 d . . . C6 C 0.0748(7) 1.0078(7) 0.7030(14) 0.036(3) Uani 1 1 d . . . H6 H 0.1264 1.0077 0.6730 0.043 Uiso 1 1 calc R . . C7 C 0.0381(8) 1.0755(6) 0.7256(14) 0.037(3) Uani 1 1 d . . . H7 H 0.0634 1.1229 0.7087 0.044 Uiso 1 1 calc R . . C100 C 0.056(3) 0.614(2) 0.862(8) 0.11(2) Uani 0.50 1 d P A -1 H10A H 0.1130 0.6000 0.8495 0.135 Uiso 0.50 1 calc PR A -1 H10B H 0.0668 0.6582 0.9414 0.135 Uiso 0.50 1 calc PR A -1 Cl1 Cl -0.0214(10) 0.6407(8) 0.6543(16) 0.094(3) Uani 0.50 1 d P A -1 Cl2 Cl 0.0205(7) 0.5370(5) 0.9522(16) 0.091(3) Uani 0.50 1 d P A -1 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 0.072(3) 0.061(2) 0.0373(17) -0.0093(15) 0.0023(16) 0.0369(19) O1 0.103(9) 0.060(7) 0.053(6) -0.013(5) -0.010(6) 0.047(6) O2 0.048(5) 0.036(4) 0.042(5) -0.006(4) 0.008(4) 0.012(4) N1 0.038(5) 0.031(5) 0.031(5) -0.003(4) 0.010(4) 0.003(4) N2 0.055(7) 0.029(5) 0.042(5) 0.002(4) 0.011(5) 0.010(5) C1 0.076(10) 0.046(8) 0.071(10) -0.025(7) 0.021(8) 0.011(7) C2 0.069(9) 0.040(7) 0.050(7) -0.012(6) 0.018(7) 0.008(6) C3 0.069(9) 0.029(6) 0.045(7) -0.004(5) 0.011(7) 0.005(6) C4 0.036(6) 0.034(6) 0.044(7) 0.002(5) 0.002(5) -0.005(5) C5 0.040(6) 0.024(5) 0.035(6) -0.006(4) 0.005(5) 0.000(4) C6 0.031(6) 0.044(7) 0.038(6) 0.006(5) 0.019(5) 0.003(5) C7 0.049(7) 0.018(5) 0.038(6) 0.002(4) 0.009(5) -0.002(5) C100 0.05(2) 0.04(2) 0.23(6) 0.04(3) 0.03(3) 0.029(17) Cl1 0.101(10) 0.092(9) 0.098(7) 0.013(6) 0.046(7) 0.014(7) Cl2 0.079(6) 0.074(6) 0.122(8) 0.015(5) 0.040(6) -0.001(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 C4 1.710(12) . ? O1 C3 1.217(16) . ? O2 C3 1.351(15) . ? O2 C2 1.415(15) . ? N1 C3 1.348(15) . ? N1 C4 1.355(15) . ? N1 H1N 0.91(2) . ? N2 C4 1.306(15) . ? N2 C5 1.449(14) . ? N2 H2N 0.92(2) . ? C1 C2 1.515(19) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C5 C6 1.386(16) . ? C5 C5 1.39(2) 6_557 ? C6 C7 1.359(16) . ? C6 H6 0.9500 . ? C7 C7 1.43(2) 6_557 ? C7 H7 0.9500 . ? C100 Cl2 1.72(5) . ? C100 Cl1 1.78(5) . ? C100 H10A 0.9900 . ? C100 H10B 0.9900 . ? 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 C3 O2 C2 117.4(10) . . ? C3 N1 C4 126.1(10) . . ? C3 N1 H1N 111(8) . . ? C4 N1 H1N 122(8) . . ? C4 N2 C5 125.9(10) . . ? C4 N2 H2N 118(9) . . ? C5 N2 H2N 116(9) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 C1 107.3(11) . . ? O2 C2 H2A 110.2 . . ? C1 C2 H2A 110.2 . . ? O2 C2 H2B 110.2 . . ? C1 C2 H2B 110.2 . . ? H2A C2 H2B 108.5 . . ? O1 C3 N1 126.0(12) . . ? O1 C3 O2 122.5(12) . . ? N1 C3 O2 111.4(11) . . ? N2 C4 N1 118.9(11) . . ? N2 C4 S1 121.8(10) . . ? N1 C4 S1 119.2(9) . . ? C6 C5 C5 120.2(7) . 6_557 ? C6 C5 N2 119.7(10) . . ? C5 C5 N2 120.1(6) 6_557 . ? C7 C6 C5 119.7(10) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C7 C7 120.0(7) . 6_557 ? C6 C7 H7 120.0 . . ? C7 C7 H7 120.0 6_557 . ? Cl2 C100 Cl1 113(3) . . ? Cl2 C100 H10A 109.0 . . ? Cl1 C100 H10A 109.0 . . ? Cl2 C100 H10B 109.0 . . ? Cl1 C100 H10B 109.0 . . ? H10A C100 H10B 107.8 . . ? 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 C3 O2 C2 C1 179.0(12) . . . . ? C4 N1 C3 O1 -5(2) . . . . ? C4 N1 C3 O2 178.2(11) . . . . ? C2 O2 C3 O1 4(2) . . . . ? C2 O2 C3 N1 -179.8(12) . . . . ? C5 N2 C4 N1 -175.1(11) . . . . ? C5 N2 C4 S1 2.5(18) . . . . ? C3 N1 C4 N2 1.3(19) . . . . ? C3 N1 C4 S1 -176.5(11) . . . . ? C4 N2 C5 C6 87.0(16) . . . . ? C4 N2 C5 C5 -94.7(17) . . . 6_557 ? C5 C5 C6 C7 -3(2) 6_557 . . . ? N2 C5 C6 C7 175.2(10) . . . . ? C5 C6 C7 C7 1(2) . . . 6_557 ? 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 H1N S1 0.91(2) 2.40(4) 3.277(10) 164(11) 7_567 N2 H2N O1 0.92(2) 1.94(10) 2.652(14) 133(12) . _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 66.94 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 0.533 _refine_diff_density_min -0.695 _refine_diff_density_rms 0.155