# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Richard Grainger' _publ_contact_author_address ; Edgbaston Birmingham B15 2TT ; _publ_contact_author_email r.s.grainger@bham.ac.uk loop_ _publ_author_name 'Bhaven Patel' 'Julie Carlisle' 'Steven E. Bottle' 'Graeme R. Hanson' 'Benson M. Kariuki' 'Louise Male' ; J.C.McMurtrie ; 'Neil Spencer' 'Richard S. Grainger' data_1.H2O _database_code_depnum_ccdc_archive 'CCDC 798806' #TrackingRef 'X-rays.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-hydroxynaphtho[1,8-de][1,3,2]dithiazine 1,1,3,3-tetraoxide monohydrate ; _chemical_name_common ;2-hydroxynaphtho(1,8-de)(1,3,2)dithiazine 1,1,3,3-tetraoxide monohydrate ; _chemical_melting_point ? _chemical_formula_moiety 'C10 H7 N O5 S2, H2 O' _chemical_formula_sum 'C10 H9 N O6 S2' _chemical_formula_weight 303.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 2(1)/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.9698(2) _cell_length_b 9.4671(3) _cell_length_c 17.7500(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.399(2) _cell_angle_gamma 90.00 _cell_volume 1167.76(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 13402 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.725 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.479 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7819 _exptl_absorpt_correction_T_max 0.9403 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Estimated minimum and maximum transmission from SADABS: 0.6755 and 0.7456 The given Tmin and Tmax were generated using the SHELX SIZE command. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16422 _diffrn_reflns_av_R_equivalents 0.0898 _diffrn_reflns_av_sigmaI/netI 0.0522 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2668 _reflns_number_gt 2241 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1067P)^2^+0.4451P] 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 2668 _refine_ls_number_parameters 179 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1599 _refine_ls_wR_factor_gt 0.1506 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8094(3) 0.0492(2) 0.12762(12) 0.0150(5) Uani 1 1 d . . . C2 C 0.8715(3) -0.0841(2) 0.14828(13) 0.0173(5) Uani 1 1 d . . . H2 H 0.9156 -0.1027 0.1993 0.021 Uiso 1 1 calc R . . C3 C 0.8701(3) -0.1934(2) 0.09426(14) 0.0184(5) Uani 1 1 d . . . H3 H 0.9096 -0.2861 0.1089 0.022 Uiso 1 1 calc R . . C4 C 0.8114(3) -0.1645(2) 0.02080(14) 0.0174(5) Uani 1 1 d . . . H4 H 0.8096 -0.2383 -0.0155 0.021 Uiso 1 1 calc R . . C5 C 0.7528(3) -0.0264(2) -0.00272(12) 0.0149(5) Uani 1 1 d . . . C6 C 0.7495(3) 0.0853(2) 0.05127(12) 0.0144(5) Uani 1 1 d . . . C7 C 0.6982(3) 0.0009(3) -0.08019(13) 0.0180(5) Uani 1 1 d . . . H7 H 0.6984 -0.0741 -0.1157 0.022 Uiso 1 1 calc R . . C8 C 0.6453(3) 0.1337(3) -0.10427(14) 0.0199(5) Uani 1 1 d . . . H8 H 0.6096 0.1503 -0.1563 0.024 Uiso 1 1 calc R . . C9 C 0.6438(3) 0.2454(3) -0.05234(13) 0.0195(5) Uani 1 1 d . . . H9 H 0.6090 0.3377 -0.0694 0.023 Uiso 1 1 calc R . . C10 C 0.6924(3) 0.2217(2) 0.02322(13) 0.0161(5) Uani 1 1 d . . . N1 N 0.8329(3) 0.3279(2) 0.15859(12) 0.0198(5) Uani 1 1 d . . . O1 O 0.9452(3) 0.15103(19) 0.25841(10) 0.0267(4) Uani 1 1 d . . . O2 O 0.6006(3) 0.17697(19) 0.22306(11) 0.0252(4) Uani 1 1 d . . . O3 O 0.7451(3) 0.49067(19) 0.04950(12) 0.0381(5) Uani 1 1 d . . . O4 O 0.4882(3) 0.3723(2) 0.11249(11) 0.0305(5) Uani 1 1 d . . . O5 O 1.0198(2) 0.31854(19) 0.13148(11) 0.0250(4) Uani 1 1 d . . . H5 H 1.0942 0.3752 0.1556 0.038 Uiso 1 1 calc R . . S1 S 0.79312(8) 0.17067(6) 0.20093(3) 0.0175(2) Uani 1 1 d . . . S2 S 0.67211(9) 0.36805(6) 0.08342(3) 0.0213(2) Uani 1 1 d . . . O101 O 0.1850(3) 0.5198(3) 0.21074(15) 0.0490(7) Uani 1 1 d D . . H01A H 0.305(3) 0.543(4) 0.217(2) 0.074 Uiso 1 1 d D . . H01B H 0.115(5) 0.582(4) 0.231(2) 0.074 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0166(11) 0.0092(10) 0.0193(11) -0.0032(8) 0.0016(9) -0.0015(8) C2 0.0197(11) 0.0124(11) 0.0197(11) 0.0007(9) 0.0012(9) -0.0015(8) C3 0.0201(11) 0.0087(10) 0.0263(13) 0.0013(9) 0.0010(9) -0.0006(8) C4 0.0168(11) 0.0102(11) 0.0256(12) -0.0051(9) 0.0047(9) -0.0027(8) C5 0.0150(11) 0.0115(11) 0.0186(11) -0.0029(8) 0.0030(8) -0.0024(8) C6 0.0144(10) 0.0103(11) 0.0184(11) -0.0011(8) 0.0006(8) -0.0018(8) C7 0.0161(11) 0.0179(12) 0.0202(11) -0.0024(9) 0.0021(9) -0.0032(9) C8 0.0199(12) 0.0219(13) 0.0176(11) 0.0024(9) 0.0001(9) -0.0013(9) C9 0.0188(12) 0.0150(11) 0.0248(12) 0.0034(9) 0.0022(9) 0.0004(9) C10 0.0159(11) 0.0086(11) 0.0236(11) -0.0007(8) 0.0013(9) -0.0005(8) N1 0.0198(11) 0.0146(10) 0.0251(11) -0.0027(8) 0.0021(8) -0.0018(8) O1 0.0336(11) 0.0209(9) 0.0240(9) -0.0064(7) -0.0087(8) 0.0045(7) O2 0.0292(10) 0.0195(10) 0.0279(10) -0.0066(7) 0.0096(8) -0.0027(7) O3 0.0658(14) 0.0095(9) 0.0381(11) 0.0024(8) -0.0018(10) -0.0058(9) O4 0.0277(10) 0.0294(11) 0.0336(11) -0.0089(8) -0.0022(8) 0.0130(8) O5 0.0205(9) 0.0217(10) 0.0336(10) -0.0096(7) 0.0069(8) -0.0058(7) S1 0.0223(4) 0.0123(3) 0.0178(3) -0.0033(2) 0.0003(2) 0.0008(2) S2 0.0293(4) 0.0083(3) 0.0259(4) -0.0023(2) -0.0010(3) 0.0031(2) O101 0.0243(11) 0.0510(15) 0.0725(17) -0.0406(13) 0.0084(11) -0.0103(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.374(3) . ? C1 C6 1.429(3) . ? C1 S1 1.747(2) . ? C2 C3 1.410(3) . ? C2 H2 0.9500 . ? C3 C4 1.364(3) . ? C3 H3 0.9500 . ? C4 C5 1.423(3) . ? C4 H4 0.9500 . ? C5 C7 1.422(3) . ? C5 C6 1.429(3) . ? C6 C10 1.429(3) . ? C7 C8 1.370(3) . ? C7 H7 0.9500 . ? C8 C9 1.403(3) . ? C8 H8 0.9500 . ? C9 C10 1.376(3) . ? C9 H9 0.9500 . ? C10 S2 1.762(2) . ? N1 O5 1.425(3) . ? N1 S1 1.699(2) . ? N1 S2 1.718(2) . ? O1 S1 1.4258(18) . ? O2 S1 1.4279(19) . ? O3 S2 1.420(2) . ? O4 S2 1.419(2) . ? O5 H5 0.8400 . ? O101 H01A 0.863(18) . ? O101 H01B 0.859(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 122.4(2) . . ? C2 C1 S1 116.28(17) . . ? C6 C1 S1 121.17(16) . . ? C1 C2 C3 120.4(2) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 119.3(2) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 121.5(2) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? C7 C5 C4 120.0(2) . . ? C7 C5 C6 119.8(2) . . ? C4 C5 C6 120.2(2) . . ? C5 C6 C1 116.1(2) . . ? C5 C6 C10 117.0(2) . . ? C1 C6 C10 126.9(2) . . ? C8 C7 C5 120.9(2) . . ? C8 C7 H7 119.5 . . ? C5 C7 H7 119.5 . . ? C7 C8 C9 120.1(2) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C10 C9 C8 120.2(2) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C6 121.9(2) . . ? C9 C10 S2 115.94(17) . . ? C6 C10 S2 122.16(17) . . ? O5 N1 S1 106.22(14) . . ? O5 N1 S2 108.06(15) . . ? S1 N1 S2 114.74(12) . . ? N1 O5 H5 109.5 . . ? O1 S1 O2 118.11(12) . . ? O1 S1 N1 107.04(11) . . ? O2 S1 N1 105.89(11) . . ? O1 S1 C1 111.09(11) . . ? O2 S1 C1 110.40(11) . . ? N1 S1 C1 103.01(10) . . ? O4 S2 O3 119.61(13) . . ? O4 S2 N1 106.11(11) . . ? O3 S2 N1 106.06(12) . . ? O4 S2 C10 111.09(11) . . ? O3 S2 C10 109.74(12) . . ? N1 S2 C10 102.65(10) . . ? H01A O101 H01B 111(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 C6 C1 C2 C3 -2.8(3) . . . . ? S1 C1 C2 C3 173.31(17) . . . . ? C1 C2 C3 C4 1.8(4) . . . . ? C2 C3 C4 C5 0.5(3) . . . . ? C3 C4 C5 C7 178.0(2) . . . . ? C3 C4 C5 C6 -1.7(3) . . . . ? C7 C5 C6 C1 -179.0(2) . . . . ? C4 C5 C6 C1 0.7(3) . . . . ? C7 C5 C6 C10 -0.8(3) . . . . ? C4 C5 C6 C10 178.9(2) . . . . ? C2 C1 C6 C5 1.5(3) . . . . ? S1 C1 C6 C5 -174.41(16) . . . . ? C2 C1 C6 C10 -176.5(2) . . . . ? S1 C1 C6 C10 7.6(3) . . . . ? C4 C5 C7 C8 -178.6(2) . . . . ? C6 C5 C7 C8 1.1(3) . . . . ? C5 C7 C8 C9 -0.2(4) . . . . ? C7 C8 C9 C10 -1.0(4) . . . . ? C8 C9 C10 C6 1.3(4) . . . . ? C8 C9 C10 S2 -176.61(18) . . . . ? C5 C6 C10 C9 -0.4(3) . . . . ? C1 C6 C10 C9 177.6(2) . . . . ? C5 C6 C10 S2 177.44(16) . . . . ? C1 C6 C10 S2 -4.6(3) . . . . ? O5 N1 S1 O1 57.25(16) . . . . ? S2 N1 S1 O1 176.56(12) . . . . ? O5 N1 S1 O2 -175.91(13) . . . . ? S2 N1 S1 O2 -56.60(15) . . . . ? O5 N1 S1 C1 -59.95(15) . . . . ? S2 N1 S1 C1 59.36(15) . . . . ? C2 C1 S1 O1 36.6(2) . . . . ? C6 C1 S1 O1 -147.20(18) . . . . ? C2 C1 S1 O2 -96.40(19) . . . . ? C6 C1 S1 O2 79.8(2) . . . . ? C2 C1 S1 N1 150.91(18) . . . . ? C6 C1 S1 N1 -32.9(2) . . . . ? O5 N1 S2 O4 178.40(13) . . . . ? S1 N1 S2 O4 60.13(15) . . . . ? O5 N1 S2 O3 -53.40(17) . . . . ? S1 N1 S2 O3 -171.67(13) . . . . ? O5 N1 S2 C10 61.74(15) . . . . ? S1 N1 S2 C10 -56.53(15) . . . . ? C9 C10 S2 O4 92.1(2) . . . . ? C6 C10 S2 O4 -85.8(2) . . . . ? C9 C10 S2 O3 -42.4(2) . . . . ? C6 C10 S2 O3 139.64(19) . . . . ? C9 C10 S2 N1 -154.87(18) . . . . ? C6 C10 S2 N1 27.2(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 O5 H5 O101 0.84 1.77 2.586(3) 162.8 1_655 O101 H01A O1 0.863(18) 2.04(2) 2.876(3) 163(4) 2_655 O101 H01B O2 0.859(19) 1.98(2) 2.814(3) 163(4) 2 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.773 _refine_diff_density_min -0.973 _refine_diff_density_rms 0.158 #============================================================================== data_1.EtOAc _database_code_depnum_ccdc_archive 'CCDC 798807' #TrackingRef 'X-rays.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-hydroxynaphtho[1,8-de][1,3,2]dithiazine 1,1,3,3-tetraoxide ethyl acetate ; _chemical_name_common ;2-hydroxynaphtho(1,8-de)(1,3,2)dithiazine 1,1,3,3-tetraoxide ethyl acetate ; _chemical_melting_point ? _chemical_formula_moiety 'C10 H7 N O5 S2, C4 H8 O2' _chemical_formula_sum 'C14 H15 N O7 S2' _chemical_formula_weight 373.39 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.1894(3) _cell_length_b 7.1236(2) _cell_length_c 18.0588(4) _cell_angle_alpha 90.00 _cell_angle_beta 112.6270(10) _cell_angle_gamma 90.00 _cell_volume 1684.87(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2434 _cell_measurement_theta_min 3.40 _cell_measurement_theta_max 70.87 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 3.207 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4462 _exptl_absorpt_correction_T_max 0.5664 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker Smart 6000 CCD' _diffrn_measurement_method 'CCD slices' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10441 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 70.87 _reflns_number_total 3067 _reflns_number_gt 2434 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SAINTPLUS _computing_data_reduction SAINTPLUS _computing_structure_solution SHELXTL _computing_structure_refinement SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0517P)^2^+0.5542P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0105(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3067 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1083 _refine_ls_wR_factor_gt 0.0992 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.67939(16) 0.3496(3) 0.13490(12) 0.0439(5) Uani 1 1 d . . . C2 C 0.66015(19) 0.3783(4) 0.20241(13) 0.0568(6) Uani 1 1 d . . . H2 H 0.7135 0.4100 0.2501 0.068 Uiso 1 1 calc R . . C3 C 0.5618(2) 0.3609(4) 0.20089(15) 0.0662(7) Uani 1 1 d . . . H3 H 0.5495 0.3811 0.2472 0.079 Uiso 1 1 calc R . . C4 C 0.48416(19) 0.3141(4) 0.13138(15) 0.0577(6) Uani 1 1 d . . . H4 H 0.4185 0.3035 0.1307 0.069 Uiso 1 1 calc R . . C5 C 0.41816(18) 0.2297(3) -0.01122(15) 0.0542(6) Uani 1 1 d . . . H5 H 0.3529 0.2198 -0.0110 0.065 Uiso 1 1 calc R . . C6 C 0.43275(19) 0.1948(3) -0.07968(15) 0.0600(7) Uani 1 1 d . . . H6 H 0.3775 0.1628 -0.1262 0.072 Uiso 1 1 calc R . . C7 C 0.53039(19) 0.2066(3) -0.08071(13) 0.0542(6) Uani 1 1 d . . . H7 H 0.5402 0.1798 -0.1276 0.065 Uiso 1 1 calc R . . C8 C 0.61176(16) 0.2575(3) -0.01297(12) 0.0430(5) Uani 1 1 d . . . C9 C 0.60026(15) 0.2980(3) 0.06040(11) 0.0386(4) Uani 1 1 d . . . C10 C 0.50015(16) 0.2809(3) 0.05978(13) 0.0441(5) Uani 1 1 d . . . C11 C 0.9377(2) -0.2344(4) -0.00511(17) 0.0716(7) Uani 1 1 d . . . H11A H 0.8907 -0.1313 -0.0225 0.107 Uiso 1 1 calc R . . H11B H 0.9011 -0.3506 -0.0205 0.107 Uiso 1 1 calc R . . H11C H 0.9868 -0.2252 -0.0296 0.107 Uiso 1 1 calc R . . C12 C 0.99072(19) -0.2282(4) 0.08261(16) 0.0566(6) Uani 1 1 d . . . C14 C 1.1059(3) -0.3899(7) 0.1986(2) 0.1274(17) Uani 1 1 d . . . H14A H 1.1530 -0.2860 0.2192 0.153 Uiso 1 1 calc R . . H14B H 1.0565 -0.3857 0.2236 0.153 Uiso 1 1 calc R . . C15 C 1.1595(6) -0.5598(10) 0.2172(3) 0.226(4) Uani 1 1 d . . . H15A H 1.2220 -0.5477 0.2088 0.340 Uiso 1 1 calc R . . H15B H 1.1185 -0.6574 0.1833 0.340 Uiso 1 1 calc R . . H15C H 1.1746 -0.5909 0.2724 0.340 Uiso 1 1 calc R . . N1 N 0.81620(14) 0.2435(3) 0.07293(11) 0.0529(5) Uani 1 1 d . . . O1 O 0.80308(13) 0.0579(2) 0.09646(10) 0.0596(4) Uani 1 1 d . . . H1 H 0.8543 -0.0042 0.1029 0.089 Uiso 1 1 calc R . . O2 O 0.87518(13) 0.3294(3) 0.21826(10) 0.0749(5) Uani 1 1 d . . . O3 O 0.81238(14) 0.5769(2) 0.11586(12) 0.0683(5) Uani 1 1 d . . . O4 O 0.74412(14) 0.4607(3) -0.04528(11) 0.0735(5) Uani 1 1 d . . . O5 O 0.74210(16) 0.1214(3) -0.06777(11) 0.0824(6) Uani 1 1 d . . . O6 O 0.97976(14) -0.1085(2) 0.12623(11) 0.0649(5) Uani 1 1 d . . . O7 O 1.05300(16) -0.3721(3) 0.11094(13) 0.0863(6) Uani 1 1 d . . . S1 S 0.80436(4) 0.39265(9) 0.14256(3) 0.0525(2) Uani 1 1 d . . . S2 S 0.72956(5) 0.27552(9) -0.02308(3) 0.0557(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0450(12) 0.0441(12) 0.0370(10) 0.0032(8) 0.0097(9) 0.0018(9) C2 0.0591(14) 0.0681(16) 0.0367(11) 0.0007(10) 0.0112(10) 0.0016(11) C3 0.0737(18) 0.085(2) 0.0460(13) 0.0059(12) 0.0295(13) 0.0065(14) C4 0.0550(14) 0.0619(15) 0.0637(15) 0.0131(12) 0.0311(12) 0.0055(11) C5 0.0430(12) 0.0438(13) 0.0651(15) 0.0087(10) 0.0090(11) -0.0028(9) C6 0.0561(15) 0.0499(15) 0.0516(14) 0.0003(11) -0.0043(11) -0.0065(11) C7 0.0701(16) 0.0449(14) 0.0379(11) -0.0006(9) 0.0100(10) 0.0005(11) C8 0.0510(12) 0.0348(11) 0.0378(10) 0.0041(8) 0.0111(9) 0.0004(9) C9 0.0443(11) 0.0307(11) 0.0367(10) 0.0059(8) 0.0109(8) -0.0002(8) C10 0.0466(12) 0.0337(11) 0.0487(12) 0.0083(9) 0.0146(9) 0.0010(8) C11 0.083(2) 0.0652(18) 0.0708(18) -0.0002(13) 0.0345(15) 0.0013(14) C12 0.0522(14) 0.0578(16) 0.0686(16) -0.0010(12) 0.0329(12) 0.0002(11) C14 0.108(3) 0.163(4) 0.081(2) -0.023(2) 0.003(2) 0.067(3) C15 0.298(9) 0.264(8) 0.103(4) 0.056(4) 0.061(5) 0.180(7) N1 0.0481(11) 0.0572(12) 0.0525(11) 0.0069(9) 0.0185(9) 0.0057(8) O1 0.0598(10) 0.0543(10) 0.0628(10) 0.0090(8) 0.0216(8) 0.0127(8) O2 0.0525(10) 0.0998(14) 0.0517(10) -0.0020(10) -0.0029(8) 0.0056(9) O3 0.0633(11) 0.0575(11) 0.0832(12) -0.0027(9) 0.0271(9) -0.0132(8) O4 0.0671(11) 0.0856(14) 0.0716(12) 0.0302(10) 0.0309(9) -0.0006(9) O5 0.0893(14) 0.1024(16) 0.0574(11) -0.0130(10) 0.0305(10) 0.0241(11) O6 0.0676(11) 0.0620(11) 0.0715(11) -0.0048(9) 0.0339(9) 0.0068(8) O7 0.0852(14) 0.0939(15) 0.0755(13) -0.0064(11) 0.0261(11) 0.0365(12) S1 0.0427(3) 0.0580(4) 0.0480(3) -0.0016(2) 0.0075(2) -0.0030(2) S2 0.0580(4) 0.0670(4) 0.0444(3) 0.0062(3) 0.0222(3) 0.0077(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.363(3) . ? C1 C9 1.429(3) . ? C1 S1 1.752(2) . ? C2 C3 1.390(4) . ? C2 H2 0.9300 . ? C3 C4 1.355(4) . ? C3 H3 0.9300 . ? C4 C10 1.416(3) . ? C4 H4 0.9300 . ? C5 C6 1.353(4) . ? C5 C10 1.408(3) . ? C5 H5 0.9300 . ? C6 C7 1.395(4) . ? C6 H6 0.9300 . ? C7 C8 1.369(3) . ? C7 H7 0.9300 . ? C8 C9 1.426(3) . ? C8 S2 1.755(2) . ? C9 C10 1.422(3) . ? C11 C12 1.470(4) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 O6 1.211(3) . ? C12 O7 1.321(3) . ? C14 C15 1.400(6) . ? C14 O7 1.473(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? N1 O1 1.423(2) . ? N1 S1 1.703(2) . ? N1 S2 1.711(2) . ? O1 H1 0.8200 . ? O2 S1 1.4229(18) . ? O3 S1 1.4178(19) . ? O4 S2 1.4171(19) . ? O5 S2 1.4136(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9 121.7(2) . . ? C2 C1 S1 116.61(17) . . ? C9 C1 S1 121.61(16) . . ? C1 C2 C3 120.9(2) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 119.5(2) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C10 121.9(2) . . ? C3 C4 H4 119.1 . . ? C10 C4 H4 119.1 . . ? C6 C5 C10 121.1(2) . . ? C6 C5 H5 119.5 . . ? C10 C5 H5 119.5 . . ? C5 C6 C7 120.2(2) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C8 C7 C6 120.3(2) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 121.7(2) . . ? C7 C8 S2 115.86(18) . . ? C9 C8 S2 122.43(16) . . ? C10 C9 C8 116.54(18) . . ? C10 C9 C1 116.76(19) . . ? C8 C9 C1 126.7(2) . . ? C5 C10 C4 120.5(2) . . ? C5 C10 C9 120.2(2) . . ? C4 C10 C9 119.3(2) . . ? C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O6 C12 O7 121.9(2) . . ? O6 C12 C11 125.6(2) . . ? O7 C12 C11 112.5(2) . . ? C15 C14 O7 109.8(4) . . ? C15 C14 H14A 109.7 . . ? O7 C14 H14A 109.7 . . ? C15 C14 H14B 109.7 . . ? O7 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O1 N1 S1 107.32(13) . . ? O1 N1 S2 107.50(14) . . ? S1 N1 S2 115.37(11) . . ? N1 O1 H1 109.5 . . ? C12 O7 C14 118.1(2) . . ? O3 S1 O2 120.03(12) . . ? O3 S1 N1 106.41(11) . . ? O2 S1 N1 106.14(11) . . ? O3 S1 C1 110.28(11) . . ? O2 S1 C1 109.86(11) . . ? N1 S1 C1 102.52(10) . . ? O5 S2 O4 119.82(13) . . ? O5 S2 N1 106.02(11) . . ? O4 S2 N1 106.53(11) . . ? O5 S2 C8 109.69(12) . . ? O4 S2 C8 110.23(10) . . ? N1 S2 C8 103.10(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C1 C2 C3 -0.9(4) . . . . ? S1 C1 C2 C3 175.4(2) . . . . ? C1 C2 C3 C4 0.2(4) . . . . ? C2 C3 C4 C10 0.4(4) . . . . ? C10 C5 C6 C7 0.9(4) . . . . ? C5 C6 C7 C8 -1.4(4) . . . . ? C6 C7 C8 C9 0.6(3) . . . . ? C6 C7 C8 S2 -177.77(18) . . . . ? C7 C8 C9 C10 0.6(3) . . . . ? S2 C8 C9 C10 178.91(14) . . . . ? C7 C8 C9 C1 179.0(2) . . . . ? S2 C8 C9 C1 -2.7(3) . . . . ? C2 C1 C9 C10 0.9(3) . . . . ? S1 C1 C9 C10 -175.19(15) . . . . ? C2 C1 C9 C8 -177.4(2) . . . . ? S1 C1 C9 C8 6.4(3) . . . . ? C6 C5 C10 C4 -178.9(2) . . . . ? C6 C5 C10 C9 0.4(3) . . . . ? C3 C4 C10 C5 179.0(2) . . . . ? C3 C4 C10 C9 -0.4(4) . . . . ? C8 C9 C10 C5 -1.1(3) . . . . ? C1 C9 C10 C5 -179.68(19) . . . . ? C8 C9 C10 C4 178.24(19) . . . . ? C1 C9 C10 C4 -0.3(3) . . . . ? O6 C12 O7 C14 3.2(4) . . . . ? C11 C12 O7 C14 -176.0(3) . . . . ? C15 C14 O7 C12 173.7(5) . . . . ? O1 N1 S1 O3 -177.05(13) . . . . ? S2 N1 S1 O3 -57.28(15) . . . . ? O1 N1 S1 O2 54.01(16) . . . . ? S2 N1 S1 O2 173.78(12) . . . . ? O1 N1 S1 C1 -61.23(15) . . . . ? S2 N1 S1 C1 58.54(13) . . . . ? C2 C1 S1 O3 -95.46(19) . . . . ? C9 C1 S1 O3 80.8(2) . . . . ? C2 C1 S1 O2 39.0(2) . . . . ? C9 C1 S1 O2 -144.67(18) . . . . ? C2 C1 S1 N1 151.54(18) . . . . ? C9 C1 S1 N1 -32.15(19) . . . . ? O1 N1 S2 O5 -51.20(17) . . . . ? S1 N1 S2 O5 -170.87(13) . . . . ? O1 N1 S2 O4 -179.88(13) . . . . ? S1 N1 S2 O4 60.45(15) . . . . ? O1 N1 S2 C8 64.05(15) . . . . ? S1 N1 S2 C8 -55.62(14) . . . . ? C7 C8 S2 O5 -43.5(2) . . . . ? C9 C8 S2 O5 138.13(18) . . . . ? C7 C8 S2 O4 90.52(19) . . . . ? C9 C8 S2 O4 -87.86(19) . . . . ? C7 C8 S2 N1 -156.08(17) . . . . ? C9 C8 S2 N1 25.54(19) . . . . ? _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 70.87 _diffrn_measured_fraction_theta_full 0.943 _refine_diff_density_max 0.257 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.046 #============================================================================== data_9 _database_code_depnum_ccdc_archive 'CCDC 798808' #TrackingRef 'X-rays.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (Z)-1,1,3,3-tetraoxidonaphtho[1,8-d,e][1,3,2]dithiazin-2-yl N-(2-cyanopropan-2-yl)isobutyimidate ; _chemical_name_common ; (Z)-1,1,3,3-tetraoxidonaphtho(1,8-d,e)(1,3,2)dithiazin-2-yl N- (2-cyanopropan-2-yl)isobutyimidate ; _chemical_melting_point ? _chemical_formula_moiety 'C18 H19 N3 O5 S2' _chemical_formula_sum 'C18 H19 N3 O5 S2' _chemical_formula_weight 421.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.1983(15) _cell_length_b 8.5889(7) _cell_length_c 15.6813(15) _cell_angle_alpha 90.00 _cell_angle_beta 95.420(10) _cell_angle_gamma 90.00 _cell_volume 2037.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5752 _cell_measurement_theta_min 3.0690 _cell_measurement_theta_max 28.7402 _exptl_crystal_description multi-faced _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.295 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.87431 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 16.0774 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 14029 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_sigmaI/netI 0.0531 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 28.87 _reflns_number_total 4719 _reflns_number_gt 3321 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET) (compiled Nov 29 2007,17:23:28) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET) (compiled Nov 29 2007,17:23:28) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET) (compiled Nov 29 2007,17:23:28) ; _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;ORTEPIII (Farrugia, 1997) WINGX-32 (Farrugia, 1999) ; _computing_publication_material 'enCIFer 1.0 (CCDC, 2003)' _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^)+(0.0400P)^2^+0.6000P] 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 4719 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0732 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1069 _refine_ls_wR_factor_gt 0.1021 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.09965(13) 0.3701(2) 0.46998(13) 0.0257(4) Uani 1 1 d . . . C2 C 0.17617(14) 0.3676(2) 0.52961(14) 0.0304(5) Uani 1 1 d . . . C3 C 0.18266(16) 0.2762(3) 0.60085(15) 0.0400(6) Uani 1 1 d . . . H3 H 0.2355 0.2769 0.6385 0.048 Uiso 1 1 calc R . . C4 C 0.11195(19) 0.1810(3) 0.61896(16) 0.0462(6) Uani 1 1 d . . . H4 H 0.1162 0.1186 0.6692 0.055 Uiso 1 1 calc R . . C5 C 0.03716(17) 0.1789(3) 0.56400(16) 0.0410(6) Uani 1 1 d . . . H5 H -0.0107 0.1142 0.5766 0.049 Uiso 1 1 calc R . . C6 C 0.02860(14) 0.2701(2) 0.48869(14) 0.0300(5) Uani 1 1 d . . . C7 C -0.04868(15) 0.2636(2) 0.43169(15) 0.0345(5) Uani 1 1 d . . . H7 H -0.0959 0.1982 0.4451 0.041 Uiso 1 1 calc R . . C8 C -0.05768(14) 0.3479(3) 0.35825(15) 0.0346(5) Uani 1 1 d . . . H8 H -0.1106 0.3413 0.3209 0.042 Uiso 1 1 calc R . . C9 C 0.01150(14) 0.4450(2) 0.33768(14) 0.0300(5) Uani 1 1 d . . . H9 H 0.0060 0.5035 0.2860 0.036 Uiso 1 1 calc R . . C10 C 0.08707(13) 0.4551(2) 0.39236(13) 0.0259(4) Uani 1 1 d . . . C11 C 0.33561(14) 0.3251(2) 0.32075(14) 0.0295(5) Uani 1 1 d . . . C12 C 0.38894(15) 0.4602(3) 0.29309(16) 0.0383(6) Uani 1 1 d . . . H11 H 0.3531 0.5573 0.2963 0.046 Uiso 1 1 calc R . . C13 C 0.4109(2) 0.4392(3) 0.20155(18) 0.0595(8) Uani 1 1 d . . . H13A H 0.4436 0.3416 0.1967 0.089 Uiso 1 1 calc R . . H13B H 0.4474 0.5266 0.1854 0.089 Uiso 1 1 calc R . . H13C H 0.3562 0.4357 0.1633 0.089 Uiso 1 1 calc R . . C14 C 0.47148(19) 0.4761(4) 0.3540(2) 0.0681(9) Uani 1 1 d . . . H12A H 0.4551 0.4916 0.4123 0.102 Uiso 1 1 calc R . . H12B H 0.5058 0.5658 0.3372 0.102 Uiso 1 1 calc R . . H12C H 0.5071 0.3814 0.3519 0.102 Uiso 1 1 calc R . . C15 C 0.30120(14) 0.0527(2) 0.33270(15) 0.0320(5) Uani 1 1 d . . . C16 C 0.33498(16) 0.0228(3) 0.42632(16) 0.0461(6) Uani 1 1 d . . . H15A H 0.3991 0.0069 0.4308 0.069 Uiso 1 1 calc R . . H15B H 0.3063 -0.0703 0.4469 0.069 Uiso 1 1 calc R . . H15C H 0.3212 0.1126 0.4612 0.069 Uiso 1 1 calc R . . C17 C 0.31969(17) -0.0877(3) 0.27706(18) 0.0458(6) Uani 1 1 d . . . H16A H 0.2980 -0.0663 0.2174 0.069 Uiso 1 1 calc R . . H16B H 0.2894 -0.1795 0.2972 0.069 Uiso 1 1 calc R . . H16C H 0.3835 -0.1073 0.2810 0.069 Uiso 1 1 calc R . . C18 C 0.20375(15) 0.0759(2) 0.32529(14) 0.0303(5) Uani 1 1 d . . . N1 N 0.26377(11) 0.5064(2) 0.40830(11) 0.0296(4) Uani 1 1 d . . . N2 N 0.34739(12) 0.1872(2) 0.29811(12) 0.0333(4) Uani 1 1 d . . . N3 N 0.12921(13) 0.0880(2) 0.31788(14) 0.0417(5) Uani 1 1 d . . . O1 O 0.34715(11) 0.3991(2) 0.54082(11) 0.0496(5) Uani 1 1 d . . . O2 O 0.25852(12) 0.6379(2) 0.54992(10) 0.0475(5) Uani 1 1 d . . . O3 O 0.16082(10) 0.73355(17) 0.39882(10) 0.0377(4) Uani 1 1 d . . . O4 O 0.17286(10) 0.57166(18) 0.27161(10) 0.0370(4) Uani 1 1 d . . . O5 O 0.26972(9) 0.35118(16) 0.37546(9) 0.0299(3) Uani 1 1 d . . . S1 S 0.26897(4) 0.48533(7) 0.51734(4) 0.03572(16) Uani 1 1 d . . . S2 S 0.16694(4) 0.58411(6) 0.36097(3) 0.02854(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0288(11) 0.0184(9) 0.0305(11) -0.0033(9) 0.0065(9) 0.0024(8) C2 0.0317(11) 0.0257(11) 0.0344(12) -0.0029(9) 0.0058(9) 0.0031(9) C3 0.0438(14) 0.0399(13) 0.0361(13) 0.0038(11) 0.0021(11) 0.0109(11) C4 0.0602(17) 0.0389(14) 0.0412(14) 0.0150(12) 0.0141(13) 0.0124(12) C5 0.0466(15) 0.0267(12) 0.0531(15) 0.0066(11) 0.0220(13) 0.0045(11) C6 0.0341(12) 0.0193(10) 0.0383(12) -0.0021(9) 0.0123(10) 0.0026(9) C7 0.0314(12) 0.0225(11) 0.0513(14) -0.0081(10) 0.0128(11) -0.0054(9) C8 0.0259(11) 0.0323(12) 0.0455(14) -0.0102(11) 0.0027(10) -0.0003(9) C9 0.0322(11) 0.0266(11) 0.0312(11) -0.0014(9) 0.0024(9) 0.0025(9) C10 0.0284(10) 0.0180(9) 0.0324(11) -0.0036(8) 0.0076(9) -0.0019(8) C11 0.0250(11) 0.0267(11) 0.0373(12) -0.0006(10) 0.0056(9) -0.0014(9) C12 0.0337(12) 0.0241(11) 0.0592(15) -0.0033(11) 0.0157(11) -0.0051(9) C13 0.0680(19) 0.0504(17) 0.0636(18) 0.0052(15) 0.0247(15) -0.0212(14) C14 0.0541(18) 0.075(2) 0.075(2) -0.0004(18) 0.0059(15) -0.0370(17) C15 0.0300(11) 0.0213(10) 0.0457(13) 0.0014(9) 0.0088(10) -0.0028(9) C16 0.0409(14) 0.0386(13) 0.0577(16) 0.0112(13) -0.0012(12) 0.0007(11) C17 0.0462(14) 0.0233(11) 0.0713(18) -0.0028(12) 0.0234(13) -0.0025(11) C18 0.0371(13) 0.0192(10) 0.0349(12) -0.0016(9) 0.0051(10) -0.0042(9) N1 0.0278(9) 0.0222(9) 0.0389(10) -0.0069(8) 0.0045(8) -0.0023(7) N2 0.0302(10) 0.0233(9) 0.0479(11) -0.0021(8) 0.0120(9) -0.0035(8) N3 0.0345(11) 0.0316(10) 0.0583(13) -0.0070(10) 0.0016(10) -0.0039(9) O1 0.0332(9) 0.0608(12) 0.0523(11) 0.0015(9) -0.0088(8) 0.0009(8) O2 0.0568(11) 0.0406(10) 0.0445(10) -0.0171(8) 0.0017(9) -0.0083(8) O3 0.0410(9) 0.0212(7) 0.0526(10) -0.0032(7) 0.0125(8) -0.0027(7) O4 0.0392(9) 0.0365(9) 0.0358(9) 0.0028(7) 0.0058(7) -0.0042(7) O5 0.0290(8) 0.0198(7) 0.0420(9) -0.0054(7) 0.0086(7) -0.0035(6) S1 0.0325(3) 0.0365(3) 0.0370(3) -0.0074(3) -0.0030(2) -0.0025(2) S2 0.0302(3) 0.0210(2) 0.0350(3) 0.0006(2) 0.0058(2) -0.0018(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 C1 C10 1.417(3) . ? C1 C2 1.422(3) . ? C1 C6 1.431(3) . ? C2 C3 1.362(3) . ? C2 S1 1.760(2) . ? C3 C4 1.400(4) . ? C3 H3 0.9500 . ? C4 C5 1.360(4) . ? C4 H4 0.9500 . ? C5 C6 1.413(3) . ? C5 H5 0.9500 . ? C6 C7 1.408(3) . ? C7 C8 1.357(3) . ? C7 H7 0.9500 . ? C8 C9 1.403(3) . ? C8 H8 0.9500 . ? C9 C10 1.370(3) . ? C9 H9 0.9500 . ? C10 S2 1.748(2) . ? C11 N2 1.255(3) . ? C11 O5 1.397(3) . ? C11 C12 1.502(3) . ? C12 C14 1.509(4) . ? C12 C13 1.515(4) . ? C12 H11 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H12A 0.9800 . ? C14 H12B 0.9800 . ? C14 H12C 0.9800 . ? C15 N2 1.481(3) . ? C15 C18 1.488(3) . ? C15 C17 1.530(3) . ? C15 C16 1.531(3) . ? C16 H15A 0.9800 . ? C16 H15B 0.9800 . ? C16 H15C 0.9800 . ? C17 H16A 0.9800 . ? C17 H16B 0.9800 . ? C17 H16C 0.9800 . ? C18 N3 1.133(3) . ? N1 O5 1.435(2) . ? N1 S1 1.7138(19) . ? N1 S2 1.7194(18) . ? O1 S1 1.4191(17) . ? O2 S1 1.4206(17) . ? O3 S2 1.4208(16) . ? O4 S2 1.4166(16) . ? 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 C10 C1 C2 127.45(19) . . ? C10 C1 C6 116.23(18) . . ? C2 C1 C6 116.26(19) . . ? C3 C2 C1 122.6(2) . . ? C3 C2 S1 115.11(17) . . ? C1 C2 S1 122.25(16) . . ? C2 C3 C4 120.4(2) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 119.4(2) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 121.8(2) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C7 C6 C5 120.9(2) . . ? C7 C6 C1 119.6(2) . . ? C5 C6 C1 119.5(2) . . ? C8 C7 C6 121.9(2) . . ? C8 C7 H7 119.0 . . ? C6 C7 H7 119.0 . . ? C7 C8 C9 119.7(2) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 119.7(2) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C1 122.85(19) . . ? C9 C10 S2 115.29(16) . . ? C1 C10 S2 121.84(15) . . ? N2 C11 O5 117.04(19) . . ? N2 C11 C12 123.5(2) . . ? O5 C11 C12 119.43(18) . . ? C11 C12 C14 109.0(2) . . ? C11 C12 C13 110.8(2) . . ? C14 C12 C13 111.4(2) . . ? C11 C12 H11 108.5 . . ? C14 C12 H11 108.5 . . ? C13 C12 H11 108.5 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H12A 109.5 . . ? C12 C14 H12B 109.5 . . ? H12A C14 H12B 109.5 . . ? C12 C14 H12C 109.5 . . ? H12A C14 H12C 109.5 . . ? H12B C14 H12C 109.5 . . ? N2 C15 C18 111.68(17) . . ? N2 C15 C17 106.68(18) . . ? C18 C15 C17 107.24(18) . . ? N2 C15 C16 110.76(18) . . ? C18 C15 C16 109.79(19) . . ? C17 C15 C16 110.60(19) . . ? C15 C16 H15A 109.5 . . ? C15 C16 H15B 109.5 . . ? H15A C16 H15B 109.5 . . ? C15 C16 H15C 109.5 . . ? H15A C16 H15C 109.5 . . ? H15B C16 H15C 109.5 . . ? C15 C17 H16A 109.5 . . ? C15 C17 H16B 109.5 . . ? H16A C17 H16B 109.5 . . ? C15 C17 H16C 109.5 . . ? H16A C17 H16C 109.5 . . ? H16B C17 H16C 109.5 . . ? N3 C18 C15 177.2(2) . . ? O5 N1 S1 105.16(12) . . ? O5 N1 S2 106.63(11) . . ? S1 N1 S2 115.38(10) . . ? C11 N2 C15 123.22(19) . . ? C11 O5 N1 116.25(15) . . ? O1 S1 O2 120.49(11) . . ? O1 S1 N1 105.81(10) . . ? O2 S1 N1 105.39(10) . . ? O1 S1 C2 109.38(11) . . ? O2 S1 C2 111.86(11) . . ? N1 S1 C2 101.99(9) . . ? O4 S2 O3 119.62(10) . . ? O4 S2 N1 105.42(9) . . ? O3 S2 N1 104.93(9) . . ? O4 S2 C10 109.96(10) . . ? O3 S2 C10 112.35(10) . . ? N1 S2 C10 102.77(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C1 C2 C3 -177.1(2) . . . . ? C6 C1 C2 C3 0.0(3) . . . . ? C10 C1 C2 S1 3.8(3) . . . . ? C6 C1 C2 S1 -179.04(15) . . . . ? C1 C2 C3 C4 -1.1(3) . . . . ? S1 C2 C3 C4 178.02(19) . . . . ? C2 C3 C4 C5 1.1(4) . . . . ? C3 C4 C5 C6 0.1(4) . . . . ? C4 C5 C6 C7 178.6(2) . . . . ? C4 C5 C6 C1 -1.1(3) . . . . ? C10 C1 C6 C7 -1.2(3) . . . . ? C2 C1 C6 C7 -178.65(19) . . . . ? C10 C1 C6 C5 178.55(19) . . . . ? C2 C1 C6 C5 1.1(3) . . . . ? C5 C6 C7 C8 -178.8(2) . . . . ? C1 C6 C7 C8 1.0(3) . . . . ? C6 C7 C8 C9 0.0(3) . . . . ? C7 C8 C9 C10 -0.7(3) . . . . ? C8 C9 C10 C1 0.5(3) . . . . ? C8 C9 C10 S2 -178.24(16) . . . . ? C2 C1 C10 C9 177.6(2) . . . . ? C6 C1 C10 C9 0.5(3) . . . . ? C2 C1 C10 S2 -3.7(3) . . . . ? C6 C1 C10 S2 179.13(15) . . . . ? N2 C11 C12 C14 -86.5(3) . . . . ? O5 C11 C12 C14 92.6(3) . . . . ? N2 C11 C12 C13 36.5(3) . . . . ? O5 C11 C12 C13 -144.4(2) . . . . ? N2 C15 C18 N3 125(5) . . . . ? C17 C15 C18 N3 8(5) . . . . ? C16 C15 C18 N3 -112(5) . . . . ? O5 C11 N2 C15 -5.8(3) . . . . ? C12 C11 N2 C15 173.4(2) . . . . ? C18 C15 N2 C11 52.4(3) . . . . ? C17 C15 N2 C11 169.2(2) . . . . ? C16 C15 N2 C11 -70.3(3) . . . . ? N2 C11 O5 N1 173.26(18) . . . . ? C12 C11 O5 N1 -5.9(3) . . . . ? S1 N1 O5 C11 -126.27(14) . . . . ? S2 N1 O5 C11 110.75(15) . . . . ? O5 N1 S1 O1 54.24(14) . . . . ? S2 N1 S1 O1 171.42(11) . . . . ? O5 N1 S1 O2 -177.08(12) . . . . ? S2 N1 S1 O2 -59.90(13) . . . . ? O5 N1 S1 C2 -60.13(13) . . . . ? S2 N1 S1 C2 57.05(12) . . . . ? C3 C2 S1 O1 40.6(2) . . . . ? C1 C2 S1 O1 -140.32(18) . . . . ? C3 C2 S1 O2 -95.53(18) . . . . ? C1 C2 S1 O2 83.57(19) . . . . ? C3 C2 S1 N1 152.29(17) . . . . ? C1 C2 S1 N1 -28.61(19) . . . . ? O5 N1 S2 O4 -56.24(14) . . . . ? S1 N1 S2 O4 -172.59(10) . . . . ? O5 N1 S2 O3 176.59(12) . . . . ? S1 N1 S2 O3 60.24(12) . . . . ? O5 N1 S2 C10 58.95(14) . . . . ? S1 N1 S2 C10 -57.40(12) . . . . ? C9 C10 S2 O4 -40.93(19) . . . . ? C1 C10 S2 O4 140.34(16) . . . . ? C9 C10 S2 O3 94.95(18) . . . . ? C1 C10 S2 O3 -83.79(18) . . . . ? C9 C10 S2 N1 -152.79(16) . . . . ? C1 C10 S2 N1 28.47(18) . . . . ? _diffrn_measured_fraction_theta_max 0.882 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.485 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.066 #============================================================================== data_12 _database_code_depnum_ccdc_archive 'CCDC 798809' #TrackingRef 'X-rays.cif' _publ_section_comment ; The structure contains four crystallographically-independent nitroxide molecules with one molecule of water per nitroxide molecule. Two of the O2SN(OH)SO2 groups are disordered over two positions with the percentage occupancy ratio of O(201)O(202)S(201)N(201)(O(205))S(202)O(203)O(204) and O(21')O(22')S(21')N(21')(O(25'))S(22')O(23')O(24') being 79(1) : 21(1) and that of O(301)O(302)S(301)N(301)(O(305))S(302)O(303)O(304) and O(31')O(32')S(31')N(31')(O(35'))S(32')O(33')O(34') being 80(1) : 20(1). In addition, the terminus of the butyl group C(111)-C(114) is disordered over two positions with the percentage occupancy ratio of C(113)-C(114) and C(13')-C(14') being 80 : 20. The hydrogen atoms belonging to the water molecules H(41A)-O(401)-H(41B) to H(71A)-O(701)-H(71B) were located in the electron density and their positions refined subject to O-H (0.88 (2) \%A) and H...H (1.41 (4) \%A) bond distance restraints. The remaining hydrogen atoms were fixed as riding models. ; # start Validation Reply Form _vrf_PLAT029_12 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.90 RESPONSE: The crystal was the best quality that could be obtained but in spite of this the diffraction data were weak, especially at higher angles. This fact can be at least partially attributed to the substantial levels of disorder in the structure. ; _vrf_PLAT731_12 ; PROBLEM: Bond Calc 0.89(12), Rep 0.881(10) ...... 9.90 su-Ra RESPONSE: These alerts have arisen from the fact that DFIX restraints were used to control the geometry of the water molecules in this structure. The calculated s.u.'s are based on reported variances only. ; _vrf_PLAT735_12 ; PROBLEM: D-H Calc 0.89(12), Rep 0.881(10) ...... 9.90 su-Ra RESPONSE: These alerts have arisen from the fact that DFIX restraints were used to control the geometry of the water molecules in this structure. The calculated s.u.'s are based on reported variances only. ; _vrf_RFACG01_12 ; PROBLEM: The value of the R factor is > 0.15 RESPONSE: The crystal was the best quality that could be obtained but in spite of this the diffraction data were weak, especially at higher angles and of somewhat poor quality. There is also a substantial amount of disorder in the structure. These issues have contributed to somewhat poor agreement statistics. ; _vrf_PLAT417_12 ; PROBLEM: Short Inter D-H..H-D H51A .. H105 .. 1.92 Ang. RESPONSE: Significat efforts were made to locate hydrogen atom positions for the water molecules which both fulfilled the hydrogen bonding requirements and did not lead to close contacts between hydrogen atoms. However, this was not always possible and the finished model is the best that could be acheived. ; _vrf_PLAT420_12 ; PROBLEM: D-H Without Acceptor O501 - H51A ... ? RESPONSE: Significat efforts were made to locate hydrogen atom positions for the water molecules which both fulfilled the hydrogen bonding requirements and did not lead to close contacts between hydrogen atoms. However, this was not always possible and the finished model is the best that could be acheived. ; _vrf_PLAT732_12 ; PROBLEM: Angle Calc 107(11), Rep 106.3(17) ...... 6.47 su-Ra RESPONSE: These alerts have arisen from the fact that DFIX restraints were used to control the geometry of the water molecules in this structure. The calculated s.u.'s are based on reported variances only. ; _vrf_PLAT415_12 ; PROBLEM: Short Inter D-H..H-X H4 .. H305 .. 2.12 Ang. RESPONSE: Significat efforts were made to locate hydrogen atom positions for the water molecules which both fulfilled the hydrogen bonding requirements and did not lead to close contacts between hydrogen atoms. However, this was not always possible and the finished model is the best that could be acheived. ; _vrf_PLAT736_12 ; PROBLEM: H...A Calc 2.10(10), Rep 2.11(4) ...... 2.50 su-Ra RESPONSE: These alerts have arisen from the fact that DFIX restraints were used to control the geometry of the water molecules in this structure. The calculated s.u.'s are based on reported variances only. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-butyl-2-hydroxynaphtho[1,8-de][1,3,2]dithiazine 1,1,3,3-tetraoxide monohydrate ; _chemical_name_common ; 4-butyl-2-hydroxynaphtho(1,8-de)(1,3,2)dithiazine 1,1,3,3- tetraoxide monohydrate ; _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 N O5 S2, H2 O' _chemical_formula_sum 'C14 H17 N O6 S2' _chemical_formula_weight 359.41 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 12.0422(14) _cell_length_b 13.3971(13) _cell_length_c 21.306(3) _cell_angle_alpha 72.268(7) _cell_angle_beta 81.717(4) _cell_angle_gamma 74.535(7) _cell_volume 3148.0(6) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 64872 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Blade _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.369 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9434 _exptl_absorpt_correction_T_max 0.9927 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 17216 reflections reduced R(int) from 0.1261 to 0.0704 Ratio of minimum to maximum apparent transmission: 0.562178 The given Tmin and Tmax were generated using the SHELX SIZE command. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28727 _diffrn_reflns_av_R_equivalents 0.1065 _diffrn_reflns_av_sigmaI/netI 0.1752 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.03 _reflns_number_total 10075 _reflns_number_gt 4982 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0000P)^2^+61.7078P] 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 10075 _refine_ls_number_parameters 981 _refine_ls_number_restraints 766 _refine_ls_R_factor_all 0.2695 _refine_ls_R_factor_gt 0.1509 _refine_ls_wR_factor_ref 0.3157 _refine_ls_wR_factor_gt 0.2496 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5429(10) 0.0889(9) 0.1610(6) 0.032(2) Uani 1 1 d U . . C2 C 0.5826(11) 0.1075(10) 0.0969(7) 0.036(3) Uani 1 1 d U . . H2 H 0.5286 0.1346 0.0638 0.043 Uiso 1 1 calc R . . C3 C 0.7003(11) 0.0880(9) 0.0776(6) 0.036(3) Uani 1 1 d U . . H3 H 0.7261 0.1024 0.0322 0.043 Uiso 1 1 calc R . . C4 C 0.7782(12) 0.0477(10) 0.1255(6) 0.037(3) Uani 1 1 d U . . H4 H 0.8586 0.0323 0.1132 0.044 Uiso 1 1 calc R . . C5 C 0.7397(10) 0.0287(9) 0.1934(6) 0.029(2) Uani 1 1 d U . . C6 C 0.6202(9) 0.0486(8) 0.2131(6) 0.023(2) Uani 1 1 d U . . C7 C 0.8222(11) -0.0105(9) 0.2424(6) 0.034(3) Uani 1 1 d U . . H7 H 0.9024 -0.0256 0.2293 0.041 Uiso 1 1 calc R . . C8 C 0.7875(11) -0.0265(10) 0.3069(6) 0.036(3) Uani 1 1 d U . . H8 H 0.8444 -0.0502 0.3382 0.043 Uiso 1 1 calc R . . C9 C 0.6690(11) -0.0091(10) 0.3301(6) 0.034(3) Uani 1 1 d U . . C10 C 0.5877(10) 0.0246(9) 0.2831(6) 0.031(2) Uani 1 1 d U . . C11 C 0.6420(11) -0.0302(10) 0.4024(6) 0.040(3) Uani 1 1 d U . . H11A H 0.5601 0.0053 0.4106 0.048 Uiso 1 1 calc R . . H11B H 0.6900 0.0033 0.4200 0.048 Uiso 1 1 calc R . . C12 C 0.6620(13) -0.1494(11) 0.4406(6) 0.048(4) Uani 1 1 d U . . H12A H 0.6161 -0.1836 0.4220 0.058 Uiso 1 1 calc R . . H12B H 0.7445 -0.1844 0.4337 0.058 Uiso 1 1 calc R . . C13 C 0.6309(12) -0.1701(11) 0.5131(6) 0.043(3) Uani 1 1 d U . . H13A H 0.5462 -0.1444 0.5199 0.051 Uiso 1 1 calc R . . H13B H 0.6676 -0.1266 0.5302 0.051 Uiso 1 1 calc R . . C14 C 0.6660(15) -0.2871(12) 0.5535(7) 0.067(5) Uani 1 1 d U . . H14A H 0.6422 -0.2927 0.6002 0.100 Uiso 1 1 calc R . . H14B H 0.7500 -0.3131 0.5483 0.100 Uiso 1 1 calc R . . H14C H 0.6284 -0.3309 0.5381 0.100 Uiso 1 1 calc R . . N1 N 0.3702(8) 0.0438(8) 0.2495(5) 0.034(2) Uani 1 1 d U . . O1 O 0.3364(7) 0.1071(7) 0.1289(5) 0.047(2) Uani 1 1 d U . . O2 O 0.3621(7) 0.2340(7) 0.1850(4) 0.042(2) Uani 1 1 d U . . O3 O 0.4213(7) -0.0414(8) 0.3656(5) 0.051(2) Uani 1 1 d U . . O4 O 0.4004(7) 0.1537(7) 0.3196(4) 0.042(2) Uani 1 1 d U . . O5 O 0.4051(7) -0.0618(6) 0.2414(5) 0.045(2) Uani 1 1 d U . . H5 H 0.3944 -0.1069 0.2776 0.068 Uiso 1 1 calc R . . S1 S 0.3936(3) 0.1296(3) 0.17577(17) 0.0347(8) Uani 1 1 d U . . S2 S 0.4402(3) 0.0467(3) 0.31299(18) 0.0387(8) Uani 1 1 d U . . C101 C 0.8753(10) 0.2516(9) 0.1756(6) 0.033(3) Uani 1 1 d U . . C102 C 0.8109(11) 0.2904(9) 0.1214(6) 0.036(3) Uani 1 1 d U . . H102 H 0.8492 0.3010 0.0785 0.043 Uiso 1 1 calc R . . C103 C 0.6914(11) 0.3142(10) 0.1278(7) 0.037(3) Uani 1 1 d U . . H103 H 0.6472 0.3399 0.0901 0.045 Uiso 1 1 calc R . . C104 C 0.6396(11) 0.2997(9) 0.1897(7) 0.038(3) Uani 1 1 d U . . H104 H 0.5576 0.3155 0.1943 0.045 Uiso 1 1 calc R . . C105 C 0.6998(10) 0.2626(9) 0.2479(6) 0.031(3) Uani 1 1 d U . . C106 C 0.8244(10) 0.2356(8) 0.2413(6) 0.026(2) Uani 1 1 d U . . C107 C 0.6425(11) 0.2545(9) 0.3106(7) 0.038(3) Uani 1 1 d U . . H107 H 0.5605 0.2719 0.3143 0.045 Uiso 1 1 calc R . . C108 C 0.6993(12) 0.2229(11) 0.3656(7) 0.045(3) Uani 1 1 d U . . H108 H 0.6572 0.2203 0.4071 0.054 Uiso 1 1 calc R . . C109 C 0.8228(12) 0.1929(10) 0.3623(7) 0.040(3) Uani 1 1 d U B . C110 C 0.8812(10) 0.1998(9) 0.3021(6) 0.033(3) Uani 1 1 d U . . C111 C 0.8782(14) 0.1593(12) 0.4286(7) 0.058(3) Uani 1 1 d U . . H11C H 0.8233 0.1308 0.4646 0.069 Uiso 1 1 calc R A 1 H11D H 0.9482 0.1005 0.4282 0.069 Uiso 1 1 calc R A 1 C112 C 0.9116(14) 0.2527(12) 0.4433(7) 0.058(3) Uani 0.80 1 d PDU B 1 H12C H 0.9496 0.2932 0.4029 0.070 Uiso 0.80 1 calc PR B 1 H12D H 0.8406 0.3027 0.4553 0.070 Uiso 0.80 1 calc PR B 1 C113 C 0.9931(16) 0.2138(17) 0.4995(8) 0.061(3) Uani 0.80 1 d PDU B 1 H13C H 1.0634 0.1626 0.4880 0.073 Uiso 0.80 1 calc PR B 1 H13D H 1.0168 0.2762 0.5044 0.073 Uiso 0.80 1 calc PR B 1 C114 C 0.9376(17) 0.1598(15) 0.5636(8) 0.063(4) Uani 0.80 1 d PDU B 1 H14D H 0.8781 0.2138 0.5798 0.094 Uiso 0.80 1 calc PR B 1 H14E H 0.9961 0.1242 0.5959 0.094 Uiso 0.80 1 calc PR B 1 H14F H 0.9022 0.1061 0.5571 0.094 Uiso 0.80 1 calc PR B 1 C12' C 0.9116(14) 0.2527(12) 0.4433(7) 0.058(3) Uani 0.20 1 d PDU B 2 H12E H 0.9846 0.2640 0.4175 0.070 Uiso 0.20 1 calc PR B 2 H12F H 0.8510 0.3195 0.4284 0.070 Uiso 0.20 1 calc PR B 2 C13' C 0.927(5) 0.234(6) 0.5144(16) 0.060(4) Uani 0.20 1 d PDU B 2 H13E H 0.8684 0.1966 0.5423 0.071 Uiso 0.20 1 calc PR B 2 H13F H 0.9168 0.3035 0.5243 0.071 Uiso 0.20 1 calc PR B 2 C14' C 1.046(5) 0.166(6) 0.528(3) 0.061(5) Uani 0.20 1 d PDU B 2 H14G H 1.0541 0.1419 0.5759 0.092 Uiso 0.20 1 calc PR B 2 H14H H 1.1026 0.2078 0.5060 0.092 Uiso 0.20 1 calc PR B 2 H14I H 1.0588 0.1024 0.5117 0.092 Uiso 0.20 1 calc PR B 2 N101 N 1.0794(8) 0.2203(8) 0.2255(5) 0.035(2) Uani 1 1 d U . . O101 O 1.0602(7) 0.2989(7) 0.1032(5) 0.046(2) Uani 1 1 d U . . O102 O 1.0621(7) 0.1080(7) 0.1535(5) 0.045(2) Uani 1 1 d U . . O103 O 1.0894(8) 0.1595(8) 0.3460(5) 0.055(3) Uani 1 1 d U . . O104 O 1.0505(7) 0.0370(7) 0.2917(5) 0.046(2) Uani 1 1 d U . . O105 O 1.0493(7) 0.3291(7) 0.2288(5) 0.045(2) Uani 1 1 d U . . H105 H 1.0717 0.3691 0.1932 0.067 Uiso 1 1 calc R . . S101 S 1.0263(3) 0.2166(3) 0.15689(18) 0.0392(8) Uani 1 1 d U . . S102 S 1.0331(3) 0.1434(3) 0.29770(18) 0.0425(9) Uani 1 1 d U . . C201 C 0.6006(11) 0.5947(10) 0.0935(7) 0.040(3) Uani 1 1 d U . . C202 C 0.6797(13) 0.5964(11) 0.0423(8) 0.053(3) Uani 1 1 d U C . H202 H 0.6560 0.6163 -0.0014 0.063 Uiso 1 1 calc R . . C203 C 0.8004(13) 0.5682(11) 0.0534(7) 0.049(3) Uani 1 1 d U . . H203 H 0.8580 0.5714 0.0177 0.059 Uiso 1 1 calc R C . C204 C 0.8289(12) 0.5363(10) 0.1180(7) 0.043(3) Uani 1 1 d U C . H204 H 0.9083 0.5166 0.1263 0.051 Uiso 1 1 calc R . . C205 C 0.7467(11) 0.5312(9) 0.1724(7) 0.035(3) Uani 1 1 d U . . C206 C 0.6252(11) 0.5622(9) 0.1615(7) 0.033(2) Uani 1 1 d U C . C207 C 0.7843(11) 0.4952(9) 0.2360(7) 0.035(3) Uani 1 1 d U C . H207 H 0.8645 0.4735 0.2428 0.042 Uiso 1 1 calc R . . C208 C 0.7040(11) 0.4916(10) 0.2885(7) 0.038(3) Uani 1 1 d U . . H208 H 0.7304 0.4683 0.3317 0.046 Uiso 1 1 calc R C . C209 C 0.5831(11) 0.5209(10) 0.2817(7) 0.035(3) Uani 1 1 d U C . C210 C 0.5488(11) 0.5541(10) 0.2184(7) 0.036(3) Uani 1 1 d U . . C211 C 0.5079(11) 0.5150(11) 0.3445(7) 0.042(3) Uani 1 1 d U . . H21A H 0.5424 0.4489 0.3785 0.050 Uiso 1 1 calc R C . H21B H 0.4313 0.5085 0.3369 0.050 Uiso 1 1 calc R . . C212 C 0.4914(12) 0.6111(11) 0.3708(7) 0.048(3) Uani 1 1 d U C . H21C H 0.5668 0.6121 0.3838 0.057 Uiso 1 1 calc R . . H21D H 0.4665 0.6777 0.3349 0.057 Uiso 1 1 calc R . . C213 C 0.4045(13) 0.6124(12) 0.4294(7) 0.054(4) Uani 1 1 d U . . H21E H 0.4234 0.5419 0.4631 0.065 Uiso 1 1 calc R C . H21F H 0.3269 0.6215 0.4150 0.065 Uiso 1 1 calc R . . C214 C 0.4005(16) 0.7013(15) 0.4607(8) 0.080(5) Uani 1 1 d U C . H21G H 0.3430 0.6974 0.4983 0.119 Uiso 1 1 calc R . . H21H H 0.3794 0.7716 0.4280 0.119 Uiso 1 1 calc R . . H21I H 0.4766 0.6921 0.4759 0.119 Uiso 1 1 calc R . . N201 N 0.3814(11) 0.5860(12) 0.1338(6) 0.049(2) Uani 0.786(8) 1 d PDU C 1 O201 O 0.4399(15) 0.6279(11) 0.0118(6) 0.059(4) Uani 0.786(8) 1 d PDU C 1 O202 O 0.4232(10) 0.7620(8) 0.0690(6) 0.049(3) Uani 0.786(8) 1 d PDU C 1 O203 O 0.3373(10) 0.5209(10) 0.2520(6) 0.055(3) Uani 0.786(8) 1 d PDU C 1 O204 O 0.3580(10) 0.7082(8) 0.2040(6) 0.049(2) Uani 0.786(8) 1 d PDU C 1 O205 O 0.4110(9) 0.4759(10) 0.1336(7) 0.051(3) Uani 0.786(8) 1 d PU C 1 H205 H 0.4297 0.4718 0.0948 0.077 Uiso 0.786(8) 1 calc PR C 1 S201 S 0.4572(3) 0.6458(4) 0.0700(2) 0.0612(11) Uani 0.786(8) 1 d PDU C 1 S202 S 0.3976(3) 0.5939(3) 0.20974(19) 0.0447(9) Uani 0.786(8) 1 d PDU C 1 N21' N 0.377(3) 0.675(3) 0.1351(9) 0.046(3) Uani 0.214(8) 1 d PDU C 2 O21' O 0.441(5) 0.703(4) 0.0025(13) 0.092(19) Uani 0.214(8) 1 d PDU C 2 O22' O 0.444(4) 0.535(2) 0.088(2) 0.066(11) Uani 0.214(8) 1 d PDU C 2 O23' O 0.343(3) 0.657(3) 0.2547(19) 0.046(3) Uani 0.214(8) 1 d PDU C 2 O24' O 0.370(4) 0.489(2) 0.224(2) 0.044(3) Uani 0.214(8) 1 d PDU C 2 O25' O 0.411(3) 0.765(3) 0.131(2) 0.047(4) Uani 0.214(8) 1 d PU C 2 H25' H 0.4040 0.8064 0.0920 0.070 Uiso 0.214(8) 1 calc PR C 2 S21' S 0.4572(3) 0.6458(4) 0.0700(2) 0.0612(11) Uani 0.214(8) 1 d PDU C 2 S22' S 0.3976(3) 0.5939(3) 0.20974(19) 0.0447(9) Uani 0.214(8) 1 d PDU C 2 C301 C 0.8798(11) 0.8086(10) 0.0713(6) 0.037(3) Uani 1 1 d U . . C302 C 0.8128(11) 0.8472(10) 0.0192(6) 0.036(3) Uani 1 1 d U D . H302 H 0.8476 0.8605 -0.0246 0.043 Uiso 1 1 calc R . . C303 C 0.6915(11) 0.8677(11) 0.0297(7) 0.045(3) Uani 1 1 d U . . H303 H 0.6447 0.8967 -0.0069 0.054 Uiso 1 1 calc R D . C304 C 0.6426(10) 0.8465(9) 0.0905(7) 0.035(3) Uani 1 1 d U D . H304 H 0.5609 0.8588 0.0969 0.042 Uiso 1 1 calc R . . C305 C 0.7109(11) 0.8052(9) 0.1469(7) 0.035(3) Uani 1 1 d U . . C306 C 0.8362(10) 0.7835(9) 0.1377(6) 0.031(2) Uani 1 1 d U D . C307 C 0.6559(11) 0.7886(9) 0.2103(7) 0.035(3) Uani 1 1 d U D . H307 H 0.5740 0.8024 0.2160 0.043 Uiso 1 1 calc R . . C308 C 0.7196(10) 0.7525(9) 0.2641(6) 0.033(3) Uani 1 1 d U . . H308 H 0.6807 0.7417 0.3068 0.039 Uiso 1 1 calc R D . C309 C 0.8424(10) 0.7303(9) 0.2586(6) 0.030(2) Uani 1 1 d U D . C310 C 0.8946(10) 0.7452(10) 0.1958(6) 0.032(2) Uani 1 1 d U . . C311 C 0.9017(14) 0.6908(11) 0.3234(7) 0.053(4) Uani 1 1 d U . . H31A H 0.8479 0.7181 0.3575 0.063 Uiso 1 1 calc R D . H31B H 0.9702 0.7213 0.3171 0.063 Uiso 1 1 calc R . . C312 C 0.9397(13) 0.5679(10) 0.3483(7) 0.052(4) Uani 1 1 d U D . H31C H 0.8707 0.5375 0.3569 0.062 Uiso 1 1 calc R . . H31D H 0.9904 0.5402 0.3135 0.062 Uiso 1 1 calc R . . C313 C 1.0035(14) 0.5299(12) 0.4109(7) 0.058(4) Uani 1 1 d U . . H31E H 0.9555 0.5634 0.4442 0.070 Uiso 1 1 calc R D . H31F H 1.0139 0.4508 0.4286 0.070 Uiso 1 1 calc R . . C314 C 1.1202(14) 0.5563(14) 0.4009(8) 0.070(5) Uani 1 1 d U D . H31G H 1.1557 0.5313 0.4432 0.104 Uiso 1 1 calc R . . H31H H 1.1109 0.6345 0.3833 0.104 Uiso 1 1 calc R . . H31I H 1.1699 0.5203 0.3696 0.104 Uiso 1 1 calc R . . N301 N 1.0856(11) 0.7833(11) 0.1165(6) 0.046(2) Uani 0.800(9) 1 d PDU D 1 O301 O 1.0622(11) 0.8462(10) -0.0063(6) 0.052(3) Uani 0.800(9) 1 d PDU D 1 O302 O 1.0657(10) 0.6580(9) 0.0548(7) 0.053(2) Uani 0.800(9) 1 d PDU D 1 O303 O 1.0945(9) 0.7422(10) 0.2368(6) 0.045(2) Uani 0.800(9) 1 d PDU D 1 O304 O 1.0885(9) 0.5962(8) 0.1912(6) 0.042(2) Uani 0.800(9) 1 d PDU D 1 O305 O 1.0481(9) 0.8953(9) 0.1138(6) 0.049(3) Uani 0.800(9) 1 d PU D 1 H305 H 1.0075 0.9283 0.0814 0.073 Uiso 0.800(9) 1 calc PR D 1 S301 S 1.0287(3) 0.7766(4) 0.0516(2) 0.0588(10) Uani 0.800(9) 1 d PDU D 1 S302 S 1.0495(3) 0.7068(3) 0.19100(17) 0.0383(8) Uani 0.800(9) 1 d PDU D 1 N31' N 1.094(4) 0.692(3) 0.1159(9) 0.049(3) Uani 0.200(9) 1 d PDU D 2 O31' O 1.059(5) 0.804(4) -0.0191(10) 0.059(4) Uani 0.200(9) 1 d PDU D 2 O32' O 1.036(4) 0.872(3) 0.070(2) 0.055(3) Uani 0.200(9) 1 d PDU D 2 O33' O 1.083(4) 0.5978(17) 0.231(2) 0.036(6) Uani 0.200(9) 1 d PDU D 2 O34' O 1.098(3) 0.788(2) 0.202(2) 0.024(7) Uani 0.200(9) 1 d PDU D 2 O35' O 1.053(4) 0.619(4) 0.097(3) 0.047(7) Uani 0.200(9) 1 d PU D 2 H35' H 1.0741 0.5573 0.1223 0.070 Uiso 0.200(9) 1 calc PR D 2 S31' S 1.0287(3) 0.7766(4) 0.0516(2) 0.0588(10) Uani 0.200(9) 1 d PDU D 2 S32' S 1.0495(3) 0.7068(3) 0.19100(17) 0.0383(8) Uani 0.200(9) 1 d PDU D 2 O401 O 0.2319(7) 0.8537(8) 0.2850(5) 0.048(3) Uani 1 1 d D E 2 H41A H 0.218(10) 0.869(11) 0.243(2) 0.072 Uiso 1 1 d D F 2 H41B H 0.171(7) 0.890(10) 0.304(5) 0.072 Uiso 1 1 d D G 2 O501 O 0.2216(8) 0.4522(7) 0.1015(5) 0.045(2) Uani 1 1 d D H 2 H51A H 0.204(12) 0.412(9) 0.141(2) 0.067 Uiso 1 1 d D I 2 H51B H 0.198(12) 0.429(10) 0.073(4) 0.067 Uiso 1 1 d D J 2 O601 O 0.2112(7) 0.3540(8) 0.2829(5) 0.049(3) Uani 1 1 d D K 2 H61A H 0.256(8) 0.307(9) 0.313(4) 0.073 Uiso 1 1 d D L 2 H61B H 0.256(8) 0.373(11) 0.247(4) 0.073 Uiso 1 1 d D M 2 O701 O 0.2529(7) 0.9316(7) 0.1091(5) 0.041(2) Uani 1 1 d D N 2 H71A H 0.179(2) 0.939(9) 0.107(7) 0.061 Uiso 1 1 d D O 2 H71B H 0.261(9) 0.989(6) 0.119(7) 0.061 Uiso 1 1 d D P 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 C1 0.032(5) 0.025(6) 0.041(6) -0.006(6) -0.009(4) -0.010(5) C2 0.040(6) 0.031(7) 0.039(6) -0.007(6) -0.016(5) -0.005(6) C3 0.048(7) 0.025(7) 0.028(6) -0.001(6) -0.001(5) -0.009(6) C4 0.042(7) 0.032(7) 0.036(6) -0.009(6) -0.002(5) -0.011(6) C5 0.027(5) 0.022(6) 0.039(5) -0.006(5) -0.014(4) -0.006(5) C6 0.025(5) 0.014(6) 0.034(5) -0.007(5) -0.004(4) -0.010(5) C7 0.029(6) 0.035(7) 0.040(6) -0.014(6) -0.012(5) -0.003(6) C8 0.032(6) 0.041(8) 0.033(6) -0.001(6) -0.006(5) -0.014(6) C9 0.036(5) 0.030(7) 0.037(5) -0.009(5) -0.005(5) -0.006(6) C10 0.030(5) 0.024(6) 0.041(5) -0.013(5) -0.006(4) -0.006(5) C11 0.037(8) 0.042(7) 0.038(6) -0.009(5) -0.002(5) -0.008(6) C12 0.061(10) 0.050(7) 0.032(6) -0.008(5) -0.006(7) -0.009(7) C13 0.044(9) 0.050(7) 0.034(7) -0.010(6) 0.000(6) -0.014(7) C14 0.093(13) 0.054(8) 0.038(9) 0.002(6) -0.009(9) -0.006(9) N1 0.023(5) 0.029(5) 0.046(5) -0.013(4) -0.009(4) 0.007(4) O1 0.037(5) 0.059(6) 0.050(6) -0.021(5) -0.013(5) -0.007(5) O2 0.041(5) 0.038(5) 0.044(6) -0.007(4) -0.012(4) -0.004(4) O3 0.034(5) 0.062(6) 0.047(6) -0.001(5) -0.001(4) -0.016(5) O4 0.038(5) 0.052(5) 0.038(6) -0.019(4) -0.014(4) 0.001(4) O5 0.043(6) 0.026(4) 0.065(7) -0.014(4) -0.002(5) -0.005(4) S1 0.0293(18) 0.0362(18) 0.037(2) -0.0068(15) -0.0106(15) -0.0042(14) S2 0.0310(19) 0.042(2) 0.039(2) -0.0090(16) -0.0038(16) -0.0045(15) C101 0.028(5) 0.030(7) 0.039(6) -0.008(6) -0.007(4) -0.003(5) C102 0.045(6) 0.032(7) 0.031(6) -0.006(6) -0.012(5) -0.007(6) C103 0.045(7) 0.030(7) 0.045(6) -0.015(6) -0.026(6) -0.006(6) C104 0.027(6) 0.027(7) 0.060(7) -0.018(7) -0.017(5) 0.007(5) C105 0.032(5) 0.025(7) 0.039(5) -0.012(6) -0.010(4) -0.007(5) C106 0.030(5) 0.015(6) 0.034(5) -0.004(5) -0.014(4) -0.003(5) C107 0.032(7) 0.026(7) 0.058(7) -0.023(6) 0.004(5) -0.003(6) C108 0.055(6) 0.050(9) 0.032(6) -0.009(7) 0.007(5) -0.024(7) C109 0.052(6) 0.034(7) 0.033(6) -0.004(6) -0.012(5) -0.009(6) C110 0.032(5) 0.030(7) 0.038(5) -0.009(6) -0.009(4) -0.004(5) C111 0.075(7) 0.057(6) 0.041(5) -0.015(5) -0.020(5) -0.006(6) C112 0.075(5) 0.060(5) 0.043(5) -0.015(4) -0.022(4) -0.011(5) C113 0.074(6) 0.063(6) 0.045(6) -0.013(5) -0.020(5) -0.009(6) C114 0.072(7) 0.065(7) 0.044(6) -0.007(6) -0.022(6) -0.004(6) C12' 0.075(5) 0.060(5) 0.043(5) -0.015(4) -0.022(4) -0.011(5) C13' 0.073(7) 0.062(6) 0.044(6) -0.013(5) -0.021(6) -0.010(6) C14' 0.070(7) 0.063(7) 0.048(7) -0.011(6) -0.018(6) -0.009(6) N101 0.015(5) 0.035(5) 0.051(5) -0.014(4) -0.006(4) 0.006(4) O101 0.030(5) 0.055(5) 0.045(5) -0.013(4) 0.005(4) -0.002(4) O102 0.035(5) 0.048(5) 0.051(6) -0.024(5) 0.002(5) 0.002(4) O103 0.043(6) 0.071(7) 0.048(6) -0.010(5) -0.026(5) -0.005(5) O104 0.036(5) 0.038(5) 0.053(6) -0.002(4) -0.010(5) -0.001(4) O105 0.042(6) 0.030(4) 0.055(6) -0.008(4) -0.002(5) -0.003(4) S101 0.0330(19) 0.041(2) 0.041(2) -0.0105(17) -0.0016(16) -0.0054(15) S102 0.036(2) 0.041(2) 0.045(2) -0.0048(17) -0.0157(17) -0.0032(16) C201 0.037(5) 0.025(6) 0.046(6) -0.003(6) -0.004(4) 0.003(5) C202 0.055(6) 0.050(9) 0.047(7) -0.013(7) 0.004(6) -0.008(7) C203 0.052(7) 0.047(9) 0.046(7) -0.018(7) 0.024(6) -0.015(7) C204 0.038(7) 0.032(7) 0.059(7) -0.017(7) 0.006(5) -0.008(6) C205 0.032(6) 0.025(7) 0.045(6) -0.002(6) 0.001(4) -0.012(5) C206 0.033(5) 0.020(6) 0.045(5) -0.013(6) -0.007(4) 0.000(5) C207 0.027(6) 0.027(7) 0.057(7) -0.023(6) -0.006(5) -0.002(5) C208 0.038(6) 0.036(7) 0.039(7) -0.004(6) -0.014(5) -0.009(6) C209 0.032(5) 0.030(7) 0.042(6) -0.004(6) -0.005(4) -0.011(5) C210 0.033(4) 0.034(7) 0.043(5) -0.014(6) -0.012(4) -0.004(4) C211 0.035(7) 0.048(8) 0.045(7) -0.008(6) -0.007(5) -0.020(6) C212 0.054(9) 0.046(8) 0.043(9) -0.013(7) -0.010(6) -0.007(7) C213 0.060(10) 0.060(9) 0.043(9) -0.008(7) -0.007(6) -0.021(8) C214 0.093(14) 0.101(14) 0.057(12) -0.039(10) 0.013(10) -0.033(11) N201 0.037(4) 0.058(4) 0.052(4) -0.021(4) -0.016(4) 0.002(4) O201 0.061(9) 0.063(9) 0.036(6) -0.006(6) -0.022(6) 0.015(9) O202 0.039(7) 0.046(6) 0.047(8) -0.006(5) -0.003(6) 0.007(5) O203 0.038(5) 0.062(5) 0.057(5) -0.001(4) -0.011(4) -0.010(4) O204 0.039(4) 0.050(4) 0.053(4) -0.016(4) -0.011(4) 0.001(4) O205 0.034(6) 0.048(5) 0.077(7) -0.025(5) -0.027(5) 0.001(5) S201 0.046(2) 0.085(3) 0.054(2) -0.031(2) -0.0112(18) 0.000(2) S202 0.0337(18) 0.0498(19) 0.051(2) -0.0140(17) -0.0104(16) -0.0067(15) N21' 0.034(5) 0.051(5) 0.051(4) -0.014(4) -0.012(4) -0.003(5) O21' 0.04(3) 0.15(5) 0.055(9) -0.02(2) -0.010(17) 0.01(4) O22' 0.06(3) 0.111(17) 0.05(3) -0.053(18) -0.01(3) -0.02(2) O23' 0.034(6) 0.051(6) 0.052(5) -0.015(5) -0.010(6) -0.004(6) O24' 0.035(5) 0.051(5) 0.049(6) -0.013(5) -0.008(5) -0.010(5) O25' 0.038(7) 0.049(6) 0.051(6) -0.012(5) -0.011(6) -0.004(5) S21' 0.046(2) 0.085(3) 0.054(2) -0.031(2) -0.0112(18) 0.000(2) S22' 0.0337(18) 0.0498(19) 0.051(2) -0.0140(17) -0.0104(16) -0.0067(15) C301 0.038(4) 0.045(8) 0.032(5) -0.016(6) -0.013(4) -0.005(5) C302 0.039(5) 0.042(8) 0.023(6) -0.012(6) 0.001(5) -0.002(6) C303 0.033(6) 0.057(9) 0.046(7) -0.016(7) -0.014(6) -0.007(7) C304 0.019(6) 0.034(7) 0.047(6) -0.004(6) -0.007(5) -0.002(5) C305 0.038(6) 0.021(6) 0.046(6) -0.014(6) -0.014(5) 0.003(5) C306 0.029(5) 0.029(7) 0.036(5) -0.006(6) -0.009(4) -0.006(5) C307 0.030(6) 0.021(6) 0.055(6) -0.013(6) -0.006(5) -0.001(5) C308 0.034(6) 0.020(6) 0.038(6) -0.006(6) 0.010(5) -0.007(5) C309 0.032(5) 0.021(6) 0.042(6) -0.015(5) -0.005(4) -0.005(5) C310 0.028(4) 0.031(7) 0.036(5) -0.008(6) 0.000(4) -0.008(4) C311 0.070(10) 0.041(7) 0.043(7) -0.010(6) -0.014(7) -0.004(7) C312 0.079(11) 0.040(7) 0.039(9) 0.008(6) -0.023(7) -0.030(7) C313 0.080(10) 0.060(9) 0.043(9) -0.005(7) -0.027(8) -0.028(8) C314 0.068(10) 0.086(13) 0.059(12) -0.016(10) -0.020(9) -0.023(9) N301 0.026(3) 0.058(4) 0.045(3) -0.010(3) -0.003(3) -0.002(3) O301 0.034(4) 0.075(5) 0.040(4) -0.010(4) -0.007(4) -0.006(5) O302 0.037(5) 0.071(4) 0.047(5) -0.016(4) -0.005(4) -0.002(4) O303 0.026(5) 0.058(5) 0.052(5) -0.014(4) -0.009(4) -0.010(4) O304 0.032(5) 0.039(4) 0.046(5) -0.011(4) -0.001(5) 0.004(4) O305 0.025(5) 0.049(5) 0.066(6) -0.011(4) -0.004(5) -0.005(4) S301 0.0365(19) 0.084(2) 0.044(2) -0.0069(19) -0.0068(16) -0.0037(18) S302 0.0245(16) 0.0458(18) 0.0417(19) -0.0106(15) -0.0070(14) -0.0025(14) N31' 0.032(5) 0.070(5) 0.042(4) -0.015(4) -0.006(4) -0.004(5) O31' 0.037(6) 0.082(6) 0.044(5) -0.006(5) -0.005(5) -0.006(6) O32' 0.031(5) 0.069(4) 0.050(5) -0.005(4) -0.002(5) -0.002(4) O33' 0.028(10) 0.036(7) 0.042(9) -0.011(7) -0.003(9) -0.007(7) O34' 0.017(10) 0.025(9) 0.018(11) 0.008(8) 0.003(9) 0.000(8) O35' 0.042(13) 0.058(8) 0.038(11) -0.019(8) -0.001(9) -0.002(9) S31' 0.0365(19) 0.084(2) 0.044(2) -0.0069(19) -0.0068(16) -0.0037(18) S32' 0.0245(16) 0.0458(18) 0.0417(19) -0.0106(15) -0.0070(14) -0.0025(14) O401 0.031(6) 0.058(6) 0.061(7) -0.032(6) -0.001(5) -0.004(5) O501 0.041(6) 0.042(6) 0.053(7) -0.016(5) -0.008(5) -0.005(4) O601 0.040(6) 0.052(6) 0.056(7) -0.015(5) -0.013(5) -0.008(5) O701 0.031(5) 0.034(5) 0.062(7) -0.017(5) -0.007(5) -0.010(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.352(17) . ? C1 C6 1.433(16) . ? C1 S1 1.746(13) . ? C2 C3 1.395(17) . ? C2 H2 0.9500 . ? C3 C4 1.372(17) . ? C3 H3 0.9500 . ? C4 C5 1.420(17) . ? C4 H4 0.9500 . ? C5 C6 1.417(16) . ? C5 C7 1.428(15) . ? C6 C10 1.444(16) . ? C7 C8 1.347(17) . ? C7 H7 0.9500 . ? C8 C9 1.423(17) . ? C8 H8 0.9500 . ? C9 C10 1.391(16) . ? C9 C11 1.484(17) . ? C10 S2 1.776(13) . ? C11 C12 1.525(17) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.493(17) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.518(18) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? N1 O5 1.421(12) . ? N1 S1 1.677(11) . ? N1 S2 1.710(10) . ? O1 S1 1.432(9) . ? O2 S1 1.415(9) . ? O3 S2 1.402(9) . ? O4 S2 1.429(9) . ? O5 H5 0.8400 . ? C101 C102 1.372(16) . ? C101 C106 1.422(17) . ? C101 S101 1.771(13) . ? C102 C103 1.384(17) . ? C102 H102 0.9500 . ? C103 C104 1.356(18) . ? C103 H103 0.9500 . ? C104 C105 1.415(17) . ? C104 H104 0.9500 . ? C105 C107 1.398(17) . ? C105 C106 1.444(16) . ? C106 C110 1.440(16) . ? C107 C108 1.340(18) . ? C107 H107 0.9500 . ? C108 C109 1.430(18) . ? C108 H108 0.9500 . ? C109 C110 1.361(18) . ? C109 C111 1.540(18) . ? C110 S102 1.783(13) . ? C111 C112 1.538(19) . ? C111 H11C 0.9900 . ? C111 H11D 0.9900 . ? C112 C113 1.534(15) . ? C112 H12C 0.9900 . ? C112 H12D 0.9900 . ? C113 C114 1.492(16) . ? C113 H13C 0.9900 . ? C113 H13D 0.9900 . ? C114 H14D 0.9800 . ? C114 H14E 0.9800 . ? C114 H14F 0.9800 . ? C13' C14' 1.50(2) . ? C13' H13E 0.9900 . ? C13' H13F 0.9900 . ? C14' H14G 0.9800 . ? C14' H14H 0.9800 . ? C14' H14I 0.9800 . ? N101 O105 1.426(12) . ? N101 S102 1.683(11) . ? N101 S101 1.697(11) . ? O101 S101 1.424(10) . ? O102 S101 1.424(9) . ? O103 S102 1.408(9) . ? O104 S102 1.428(9) . ? O105 H105 0.8400 . ? C201 C202 1.340(18) . ? C201 C206 1.431(18) . ? C201 S201 1.764(13) . ? C202 C203 1.436(19) . ? C202 H202 0.9500 . ? C203 C204 1.377(19) . ? C203 H203 0.9500 . ? C204 C205 1.410(18) . ? C204 H204 0.9500 . ? C205 C207 1.391(17) . ? C205 C206 1.443(16) . ? C206 C210 1.407(18) . ? C207 C208 1.367(17) . ? C207 H207 0.9500 . ? C208 C209 1.420(17) . ? C208 H208 0.9500 . ? C209 C210 1.373(17) . ? C209 C211 1.498(18) . ? C210 S202 1.775(13) . ? C211 C212 1.511(18) . ? C211 H21A 0.9900 . ? C211 H21B 0.9900 . ? C212 C213 1.510(19) . ? C212 H21C 0.9900 . ? C212 H21D 0.9900 . ? C213 C214 1.52(2) . ? C213 H21E 0.9900 . ? C213 H21F 0.9900 . ? C214 H21G 0.9800 . ? C214 H21H 0.9800 . ? C214 H21I 0.9800 . ? N201 O205 1.424(18) . ? N201 S201 1.640(13) . ? N201 S202 1.696(12) . ? O201 S201 1.385(11) . ? O202 S201 1.495(10) . ? O203 S202 1.396(11) . ? O204 S202 1.449(10) . ? O205 H205 0.8400 . ? N21' O25' 1.35(6) . ? N21' S21' 1.66(3) . ? N21' S22' 1.64(2) . ? O21' S21' 1.42(3) . ? O22' S21' 1.46(3) . ? O23' S22' 1.44(4) . ? O24' S22' 1.46(3) . ? O25' H25' 0.8400 . ? C301 C302 1.357(16) . ? C301 C306 1.406(17) . ? C301 S301 1.749(14) . ? C302 C303 1.410(17) . ? C302 H302 0.9500 . ? C303 C304 1.323(18) . ? C303 H303 0.9500 . ? C304 C305 1.437(17) . ? C304 H304 0.9500 . ? C305 C307 1.397(18) . ? C305 C306 1.454(17) . ? C306 C310 1.402(16) . ? C307 C308 1.361(17) . ? C307 H307 0.9500 . ? C308 C309 1.423(16) . ? C308 H308 0.9500 . ? C309 C310 1.373(17) . ? C309 C311 1.529(17) . ? C310 S302 1.794(12) . ? C311 C312 1.529(18) . ? C311 H31A 0.9900 . ? C311 H31B 0.9900 . ? C312 C313 1.516(17) . ? C312 H31C 0.9900 . ? C312 H31D 0.9900 . ? C313 C314 1.51(2) . ? C313 H31E 0.9900 . ? C313 H31F 0.9900 . ? C314 H31G 0.9800 . ? C314 H31H 0.9800 . ? C314 H31I 0.9800 . ? N301 O305 1.432(17) . ? N301 S301 1.666(12) . ? N301 S302 1.676(12) . ? O301 S301 1.382(11) . ? O302 S301 1.514(11) . ? O303 S302 1.429(10) . ? O304 S302 1.428(10) . ? O305 H305 0.8400 . ? N31' O35' 1.39(7) . ? N31' S31' 1.63(3) . ? N31' S32' 1.67(2) . ? O31' S31' 1.45(2) . ? O32' S31' 1.47(4) . ? O33' S32' 1.43(3) . ? O34' S32' 1.45(3) . ? O35' H35' 0.8400 . ? O401 H41A 0.880(10) . ? O401 H41B 0.881(10) . ? O501 H51A 0.879(10) . ? O501 H51B 0.879(10) . ? O601 H61A 0.880(10) . ? O601 H61B 0.880(10) . ? O701 H71A 0.879(10) . ? O701 H71B 0.878(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 121.4(12) . . ? C2 C1 S1 115.9(9) . . ? C6 C1 S1 122.4(10) . . ? C1 C2 C3 122.2(12) . . ? C1 C2 H2 118.9 . . ? C3 C2 H2 118.9 . . ? C4 C3 C2 118.8(12) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C3 C4 C5 120.7(12) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 120.7(11) . . ? C6 C5 C7 119.6(12) . . ? C4 C5 C7 119.7(11) . . ? C5 C6 C1 116.2(11) . . ? C5 C6 C10 117.6(10) . . ? C1 C6 C10 126.2(11) . . ? C8 C7 C5 120.6(12) . . ? C8 C7 H7 119.7 . . ? C5 C7 H7 119.7 . . ? C7 C8 C9 122.6(12) . . ? C7 C8 H8 118.7 . . ? C9 C8 H8 118.7 . . ? C10 C9 C8 117.3(12) . . ? C10 C9 C11 125.2(12) . . ? C8 C9 C11 117.4(11) . . ? C9 C10 C6 122.1(11) . . ? C9 C10 S2 116.6(10) . . ? C6 C10 S2 121.2(9) . . ? C9 C11 C12 114.6(11) . . ? C9 C11 H11A 108.6 . . ? C12 C11 H11A 108.6 . . ? C9 C11 H11B 108.6 . . ? C12 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? C13 C12 C11 114.4(11) . . ? C13 C12 H12A 108.7 . . ? C11 C12 H12A 108.7 . . ? C13 C12 H12B 108.7 . . ? C11 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C12 C13 C14 115.3(12) . . ? C12 C13 H13A 108.4 . . ? C14 C13 H13A 108.4 . . ? C12 C13 H13B 108.4 . . ? C14 C13 H13B 108.4 . . ? H13A C13 H13B 107.5 . . ? 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 . . ? O5 N1 S1 107.1(8) . . ? O5 N1 S2 108.5(7) . . ? S1 N1 S2 116.1(6) . . ? N1 O5 H5 109.5 . . ? O2 S1 O1 119.3(5) . . ? O2 S1 N1 106.5(5) . . ? O1 S1 N1 107.0(5) . . ? O2 S1 C1 110.8(5) . . ? O1 S1 C1 109.6(6) . . ? N1 S1 C1 102.1(5) . . ? O3 S2 O4 120.1(6) . . ? O3 S2 N1 105.2(6) . . ? O4 S2 N1 106.1(5) . . ? O3 S2 C10 110.6(6) . . ? O4 S2 C10 109.8(6) . . ? N1 S2 C10 103.6(5) . . ? C102 C101 C106 122.6(12) . . ? C102 C101 S101 114.3(10) . . ? C106 C101 S101 123.0(9) . . ? C101 C102 C103 121.5(13) . . ? C101 C102 H102 119.2 . . ? C103 C102 H102 119.2 . . ? C104 C103 C102 117.6(12) . . ? C104 C103 H103 121.2 . . ? C102 C103 H103 121.2 . . ? C103 C104 C105 124.3(12) . . ? C103 C104 H104 117.9 . . ? C105 C104 H104 117.9 . . ? C107 C105 C104 122.2(12) . . ? C107 C105 C106 119.7(11) . . ? C104 C105 C106 118.1(12) . . ? C101 C106 C110 128.3(11) . . ? C101 C106 C105 115.8(10) . . ? C110 C106 C105 115.8(11) . . ? C108 C107 C105 122.3(13) . . ? C108 C107 H107 118.8 . . ? C105 C107 H107 118.8 . . ? C107 C108 C109 120.5(13) . . ? C107 C108 H108 119.8 . . ? C109 C108 H108 119.8 . . ? C110 C109 C108 118.7(12) . . ? C110 C109 C111 125.5(13) . . ? C108 C109 C111 115.7(13) . . ? C109 C110 C106 123.0(12) . . ? C109 C110 S102 119.2(10) . . ? C106 C110 S102 117.1(10) . . ? C112 C111 C109 113.1(11) . . ? C112 C111 H11C 109.0 . . ? C109 C111 H11C 109.0 . . ? C112 C111 H11D 109.0 . . ? C109 C111 H11D 109.0 . . ? H11C C111 H11D 107.8 . . ? C113 C112 C111 112.6(13) . . ? C113 C112 H12C 109.1 . . ? C111 C112 H12C 109.1 . . ? C113 C112 H12D 109.1 . . ? C111 C112 H12D 109.1 . . ? H12C C112 H12D 107.8 . . ? C114 C113 C112 112.0(14) . . ? C114 C113 H13C 109.2 . . ? C112 C113 H13C 109.2 . . ? C114 C113 H13D 109.2 . . ? C112 C113 H13D 109.2 . . ? H13C C113 H13D 107.9 . . ? C113 C114 H14D 109.5 . . ? C113 C114 H14E 109.5 . . ? H14D C114 H14E 109.5 . . ? C113 C114 H14F 109.5 . . ? H14D C114 H14F 109.5 . . ? H14E C114 H14F 109.5 . . ? C14' C13' H13E 110.2 . . ? C14' C13' H13F 110.2 . . ? H13E C13' H13F 108.5 . . ? C13' C14' H14G 109.5 . . ? C13' C14' H14H 109.5 . . ? H14G C14' H14H 109.5 . . ? C13' C14' H14I 109.5 . . ? H14G C14' H14I 109.5 . . ? H14H C14' H14I 109.5 . . ? O105 N101 S102 107.8(8) . . ? O105 N101 S101 108.5(7) . . ? S102 N101 S101 115.9(6) . . ? N101 O105 H105 109.5 . . ? O101 S101 O102 118.6(6) . . ? O101 S101 N101 107.1(6) . . ? O102 S101 N101 107.0(5) . . ? O101 S101 C101 110.2(6) . . ? O102 S101 C101 110.4(6) . . ? N101 S101 C101 102.2(6) . . ? O103 S102 O104 119.2(6) . . ? O103 S102 N101 104.9(6) . . ? O104 S102 N101 107.9(6) . . ? O103 S102 C110 112.7(6) . . ? O104 S102 C110 107.6(6) . . ? N101 S102 C110 103.2(5) . . ? C202 C201 C206 125.4(13) . . ? C202 C201 S201 113.7(11) . . ? C206 C201 S201 120.8(10) . . ? C201 C202 C203 120.0(14) . . ? C201 C202 H202 120.0 . . ? C203 C202 H202 120.0 . . ? C204 C203 C202 116.9(13) . . ? C204 C203 H203 121.5 . . ? C202 C203 H203 121.5 . . ? C203 C204 C205 123.6(13) . . ? C203 C204 H204 118.2 . . ? C205 C204 H204 118.2 . . ? C207 C205 C204 119.2(12) . . ? C207 C205 C206 121.1(12) . . ? C204 C205 C206 119.6(12) . . ? C210 C206 C201 129.5(12) . . ? C210 C206 C205 116.2(11) . . ? C201 C206 C205 114.3(12) . . ? C208 C207 C205 118.9(12) . . ? C208 C207 H207 120.6 . . ? C205 C207 H207 120.6 . . ? C207 C208 C209 123.3(12) . . ? C207 C208 H208 118.3 . . ? C209 C208 H208 118.3 . . ? C210 C209 C208 116.4(12) . . ? C210 C209 C211 127.6(12) . . ? C208 C209 C211 115.9(11) . . ? C209 C210 C206 124.1(12) . . ? C209 C210 S202 116.4(11) . . ? C206 C210 S202 119.4(10) . . ? C209 C211 C212 114.1(11) . . ? C209 C211 H21A 108.7 . . ? C212 C211 H21A 108.7 . . ? C209 C211 H21B 108.7 . . ? C212 C211 H21B 108.7 . . ? H21A C211 H21B 107.6 . . ? C213 C212 C211 114.4(12) . . ? C213 C212 H21C 108.7 . . ? C211 C212 H21C 108.7 . . ? C213 C212 H21D 108.7 . . ? C211 C212 H21D 108.7 . . ? H21C C212 H21D 107.6 . . ? C212 C213 C214 113.5(13) . . ? C212 C213 H21E 108.9 . . ? C214 C213 H21E 108.9 . . ? C212 C213 H21F 108.9 . . ? C214 C213 H21F 108.9 . . ? H21E C213 H21F 107.7 . . ? C213 C214 H21G 109.5 . . ? C213 C214 H21H 109.5 . . ? H21G C214 H21H 109.5 . . ? C213 C214 H21I 109.5 . . ? H21G C214 H21I 109.5 . . ? H21H C214 H21I 109.5 . . ? O205 N201 S201 104.8(10) . . ? O205 N201 S202 109.4(10) . . ? S201 N201 S202 118.9(8) . . ? N201 O205 H205 109.5 . . ? O201 S201 O202 113.8(8) . . ? O201 S201 N201 112.6(9) . . ? O202 S201 N201 104.6(7) . . ? O201 S201 C201 113.9(8) . . ? O202 S201 C201 107.3(6) . . ? N201 S201 C201 103.7(7) . . ? O203 S202 O204 120.4(8) . . ? O203 S202 N201 103.3(8) . . ? O204 S202 N201 103.5(7) . . ? O203 S202 C210 113.6(7) . . ? O204 S202 C210 109.0(6) . . ? N201 S202 C210 105.3(7) . . ? O25' N21' S21' 97(2) . . ? O25' N21' S22' 108(2) . . ? S21' N21' S22' 121(2) . . ? N21' O25' H25' 109.5 . . ? C302 C301 C306 123.9(12) . . ? C302 C301 S301 115.5(10) . . ? C306 C301 S301 120.2(9) . . ? C301 C302 C303 120.1(13) . . ? C301 C302 H302 119.9 . . ? C303 C302 H302 119.9 . . ? C304 C303 C302 120.2(12) . . ? C304 C303 H303 119.9 . . ? C302 C303 H303 119.9 . . ? C303 C304 C305 121.2(12) . . ? C303 C304 H304 119.4 . . ? C305 C304 H304 119.4 . . ? C307 C305 C304 119.5(12) . . ? C307 C305 C306 120.6(11) . . ? C304 C305 C306 119.9(12) . . ? C310 C306 C301 129.9(12) . . ? C310 C306 C305 115.4(12) . . ? C301 C306 C305 114.6(11) . . ? C308 C307 C305 120.0(12) . . ? C308 C307 H307 120.0 . . ? C305 C307 H307 120.0 . . ? C307 C308 C309 122.4(12) . . ? C307 C308 H308 118.8 . . ? C309 C308 H308 118.8 . . ? C310 C309 C308 116.6(11) . . ? C310 C309 C311 127.2(12) . . ? C308 C309 C311 116.2(12) . . ? C309 C310 C306 125.0(12) . . ? C309 C310 S302 115.3(9) . . ? C306 C310 S302 119.6(10) . . ? C309 C311 C312 113.2(11) . . ? C309 C311 H31A 108.9 . . ? C312 C311 H31A 108.9 . . ? C309 C311 H31B 108.9 . . ? C312 C311 H31B 108.9 . . ? H31A C311 H31B 107.8 . . ? C313 C312 C311 112.7(12) . . ? C313 C312 H31C 109.1 . . ? C311 C312 H31C 109.1 . . ? C313 C312 H31D 109.1 . . ? C311 C312 H31D 109.1 . . ? H31C C312 H31D 107.8 . . ? C314 C313 C312 113.7(13) . . ? C314 C313 H31E 108.8 . . ? C312 C313 H31E 108.8 . . ? C314 C313 H31F 108.8 . . ? C312 C313 H31F 108.8 . . ? H31E C313 H31F 107.7 . . ? C313 C314 H31G 109.5 . . ? C313 C314 H31H 109.5 . . ? H31G C314 H31H 109.5 . . ? C313 C314 H31I 109.5 . . ? H31G C314 H31I 109.5 . . ? H31H C314 H31I 109.5 . . ? O305 N301 S301 103.2(9) . . ? O305 N301 S302 110.5(10) . . ? S301 N301 S302 117.5(8) . . ? N301 O305 H305 109.5 . . ? O301 S301 O302 115.6(8) . . ? O301 S301 N301 111.5(8) . . ? O302 S301 N301 103.7(7) . . ? O301 S301 C301 112.9(7) . . ? O302 S301 C301 108.2(7) . . ? N301 S301 C301 103.9(6) . . ? O304 S302 O303 118.5(7) . . ? O304 S302 N301 108.4(7) . . ? O303 S302 N301 104.7(7) . . ? O304 S302 C310 110.0(6) . . ? O303 S302 C310 110.9(6) . . ? N301 S302 C310 103.1(6) . . ? O35' N31' S31' 82(3) . . ? O35' N31' S32' 117(4) . . ? S31' N31' S32' 120(3) . . ? N31' O35' H35' 109.5 . . ? H41A O401 H41B 106.3(17) . . ? H51A O501 H51B 106.8(17) . . ? H61A O601 H61B 106.5(17) . . ? H71A O701 H71B 107.0(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.4(18) . . . . ? S1 C1 C2 C3 174.3(9) . . . . ? C1 C2 C3 C4 0.7(18) . . . . ? C2 C3 C4 C5 -1.6(17) . . . . ? C3 C4 C5 C6 1.5(17) . . . . ? C3 C4 C5 C7 -178.3(11) . . . . ? C4 C5 C6 C1 -0.5(15) . . . . ? C7 C5 C6 C1 179.4(10) . . . . ? C4 C5 C6 C10 178.3(10) . . . . ? C7 C5 C6 C10 -1.9(15) . . . . ? C2 C1 C6 C5 -0.5(16) . . . . ? S1 C1 C6 C5 -174.0(8) . . . . ? C2 C1 C6 C10 -179.1(11) . . . . ? S1 C1 C6 C10 7.4(16) . . . . ? C6 C5 C7 C8 -1.5(17) . . . . ? C4 C5 C7 C8 178.3(11) . . . . ? C5 C7 C8 C9 2.2(19) . . . . ? C7 C8 C9 C10 0.6(18) . . . . ? C7 C8 C9 C11 179.6(11) . . . . ? C8 C9 C10 C6 -4.2(17) . . . . ? C11 C9 C10 C6 176.9(11) . . . . ? C8 C9 C10 S2 -179.5(9) . . . . ? C11 C9 C10 S2 1.6(16) . . . . ? C5 C6 C10 C9 4.8(16) . . . . ? C1 C6 C10 C9 -176.6(11) . . . . ? C5 C6 C10 S2 179.9(8) . . . . ? C1 C6 C10 S2 -1.4(15) . . . . ? C10 C9 C11 C12 103.4(15) . . . . ? C8 C9 C11 C12 -75.5(15) . . . . ? C9 C11 C12 C13 -178.0(11) . . . . ? C11 C12 C13 C14 -171.5(13) . . . . ? O5 N1 S1 O2 -178.1(7) . . . . ? S2 N1 S1 O2 -56.7(7) . . . . ? O5 N1 S1 O1 53.3(8) . . . . ? S2 N1 S1 O1 174.7(6) . . . . ? O5 N1 S1 C1 -61.8(8) . . . . ? S2 N1 S1 C1 59.5(7) . . . . ? C2 C1 S1 O2 -94.8(10) . . . . ? C6 C1 S1 O2 79.1(10) . . . . ? C2 C1 S1 O1 38.9(11) . . . . ? C6 C1 S1 O1 -147.2(9) . . . . ? C2 C1 S1 N1 152.2(9) . . . . ? C6 C1 S1 N1 -34.0(10) . . . . ? O5 N1 S2 O3 -50.7(9) . . . . ? S1 N1 S2 O3 -171.4(6) . . . . ? O5 N1 S2 O4 -179.0(8) . . . . ? S1 N1 S2 O4 60.4(7) . . . . ? O5 N1 S2 C10 65.4(9) . . . . ? S1 N1 S2 C10 -55.2(7) . . . . ? C9 C10 S2 O3 -49.1(11) . . . . ? C6 C10 S2 O3 135.5(9) . . . . ? C9 C10 S2 O4 85.7(10) . . . . ? C6 C10 S2 O4 -89.8(10) . . . . ? C9 C10 S2 N1 -161.4(9) . . . . ? C6 C10 S2 N1 23.2(10) . . . . ? C106 C101 C102 C103 -1.4(18) . . . . ? S101 C101 C102 C103 175.4(9) . . . . ? C101 C102 C103 C104 1.1(18) . . . . ? C102 C103 C104 C105 0.5(18) . . . . ? C103 C104 C105 C107 176.5(12) . . . . ? C103 C104 C105 C106 -1.7(17) . . . . ? C102 C101 C106 C110 -177.3(12) . . . . ? S101 C101 C106 C110 6.1(17) . . . . ? C102 C101 C106 C105 0.1(16) . . . . ? S101 C101 C106 C105 -176.4(8) . . . . ? C107 C105 C106 C101 -176.9(11) . . . . ? C104 C105 C106 C101 1.4(15) . . . . ? C107 C105 C106 C110 0.9(15) . . . . ? C104 C105 C106 C110 179.1(10) . . . . ? C104 C105 C107 C108 -177.7(12) . . . . ? C106 C105 C107 C108 0.5(18) . . . . ? C105 C107 C108 C109 -1.8(19) . . . . ? C107 C108 C109 C110 1.7(19) . . . . ? C107 C108 C109 C111 179.3(12) . . . . ? C108 C109 C110 C106 -0.3(19) . . . . ? C111 C109 C110 C106 -177.6(12) . . . . ? C108 C109 C110 S102 -170.3(10) . . . . ? C111 C109 C110 S102 12.4(18) . . . . ? C101 C106 C110 C109 176.4(12) . . . . ? C105 C106 C110 C109 -1.0(17) . . . . ? C101 C106 C110 S102 -13.3(16) . . . . ? C105 C106 C110 S102 169.2(8) . . . . ? C110 C109 C111 C112 82.7(17) . . . . ? C108 C109 C111 C112 -94.7(16) . . . . ? C109 C111 C112 C113 -165.5(14) . . . . ? C111 C112 C113 C114 -64(2) . . . . ? O105 N101 S101 O101 49.4(9) . . . . ? S102 N101 S101 O101 170.7(6) . . . . ? O105 N101 S101 O102 177.5(7) . . . . ? S102 N101 S101 O102 -61.2(7) . . . . ? O105 N101 S101 C101 -66.5(8) . . . . ? S102 N101 S101 C101 54.9(7) . . . . ? C102 C101 S101 O101 45.3(11) . . . . ? C106 C101 S101 O101 -137.9(10) . . . . ? C102 C101 S101 O102 -87.6(10) . . . . ? C106 C101 S101 O102 89.2(11) . . . . ? C102 C101 S101 N101 158.9(9) . . . . ? C106 C101 S101 N101 -24.3(11) . . . . ? O105 N101 S102 O103 -58.9(8) . . . . ? S101 N101 S102 O103 179.4(6) . . . . ? O105 N101 S102 O104 173.1(7) . . . . ? S101 N101 S102 O104 51.4(7) . . . . ? O105 N101 S102 C110 59.4(8) . . . . ? S101 N101 S102 C110 -62.3(7) . . . . ? C109 C110 S102 O103 -38.7(12) . . . . ? C106 C110 S102 O103 150.7(9) . . . . ? C109 C110 S102 O104 94.7(11) . . . . ? C106 C110 S102 O104 -75.9(10) . . . . ? C109 C110 S102 N101 -151.4(10) . . . . ? C106 C110 S102 N101 38.0(10) . . . . ? C206 C201 C202 C203 -3(2) . . . . ? S201 C201 C202 C203 173.4(10) . . . . ? C201 C202 C203 C204 2(2) . . . . ? C202 C203 C204 C205 -0.6(19) . . . . ? C203 C204 C205 C207 178.4(12) . . . . ? C203 C204 C205 C206 -1.0(18) . . . . ? C202 C201 C206 C210 -177.6(13) . . . . ? S201 C201 C206 C210 6.7(18) . . . . ? C202 C201 C206 C205 1.0(18) . . . . ? S201 C201 C206 C205 -174.8(9) . . . . ? C207 C205 C206 C210 0.2(16) . . . . ? C204 C205 C206 C210 179.6(11) . . . . ? C207 C205 C206 C201 -178.5(11) . . . . ? C204 C205 C206 C201 0.9(16) . . . . ? C204 C205 C207 C208 179.3(11) . . . . ? C206 C205 C207 C208 -1.3(17) . . . . ? C205 C207 C208 C209 1.2(18) . . . . ? C207 C208 C209 C210 0.0(18) . . . . ? C207 C208 C209 C211 -178.3(11) . . . . ? C208 C209 C210 C206 -1.1(18) . . . . ? C211 C209 C210 C206 176.9(12) . . . . ? C208 C209 C210 S202 -178.5(9) . . . . ? C211 C209 C210 S202 -0.5(17) . . . . ? C201 C206 C210 C209 179.5(12) . . . . ? C205 C206 C210 C209 1.0(18) . . . . ? C201 C206 C210 S202 -3.2(18) . . . . ? C205 C206 C210 S202 178.3(8) . . . . ? C210 C209 C211 C212 -97.6(15) . . . . ? C208 C209 C211 C212 80.4(14) . . . . ? C209 C211 C212 C213 172.9(11) . . . . ? C211 C212 C213 C214 172.4(13) . . . . ? O205 N201 S201 O201 54.2(11) . . . . ? S202 N201 S201 O201 176.8(9) . . . . ? O205 N201 S201 O202 178.3(8) . . . . ? S202 N201 S201 O202 -59.2(10) . . . . ? O205 N201 S201 C201 -69.4(9) . . . . ? S202 N201 S201 C201 53.2(10) . . . . ? C202 C201 S201 O201 31.8(14) . . . . ? C206 C201 S201 O201 -152.0(11) . . . . ? C202 C201 S201 O202 -95.1(12) . . . . ? C206 C201 S201 O202 81.1(11) . . . . ? C202 C201 S201 N201 154.5(11) . . . . ? C206 C201 S201 N201 -29.3(12) . . . . ? O205 N201 S202 O203 -50.1(11) . . . . ? S201 N201 S202 O203 -170.4(9) . . . . ? O205 N201 S202 O204 -176.4(9) . . . . ? S201 N201 S202 O204 63.3(11) . . . . ? O205 N201 S202 C210 69.2(10) . . . . ? S201 N201 S202 C210 -51.0(11) . . . . ? C209 C210 S202 O203 -47.7(13) . . . . ? C206 C210 S202 O203 134.8(11) . . . . ? C209 C210 S202 O204 89.5(11) . . . . ? C206 C210 S202 O204 -88.0(11) . . . . ? C209 C210 S202 N201 -160.0(10) . . . . ? C206 C210 S202 N201 22.5(12) . . . . ? C306 C301 C302 C303 2(2) . . . . ? S301 C301 C302 C303 175.1(10) . . . . ? C301 C302 C303 C304 -2(2) . . . . ? C302 C303 C304 C305 2(2) . . . . ? C303 C304 C305 C307 177.1(12) . . . . ? C303 C304 C305 C306 -1.5(18) . . . . ? C302 C301 C306 C310 -178.7(13) . . . . ? S301 C301 C306 C310 8.4(19) . . . . ? C302 C301 C306 C305 -1.7(18) . . . . ? S301 C301 C306 C305 -174.6(9) . . . . ? C307 C305 C306 C310 0.3(16) . . . . ? C304 C305 C306 C310 178.9(11) . . . . ? C307 C305 C306 C301 -177.1(11) . . . . ? C304 C305 C306 C301 1.5(16) . . . . ? C304 C305 C307 C308 -178.1(11) . . . . ? C306 C305 C307 C308 0.5(17) . . . . ? C305 C307 C308 C309 -0.1(17) . . . . ? C307 C308 C309 C310 -1.2(17) . . . . ? C307 C308 C309 C311 179.7(11) . . . . ? C308 C309 C310 C306 2.1(17) . . . . ? C311 C309 C310 C306 -178.8(12) . . . . ? C308 C309 C310 S302 -175.5(8) . . . . ? C311 C309 C310 S302 3.6(16) . . . . ? C301 C306 C310 C309 175.3(12) . . . . ? C305 C306 C310 C309 -1.7(17) . . . . ? C301 C306 C310 S302 -7.3(18) . . . . ? C305 C306 C310 S302 175.8(8) . . . . ? C310 C309 C311 C312 -84.1(17) . . . . ? C308 C309 C311 C312 95.0(14) . . . . ? C309 C311 C312 C313 177.2(13) . . . . ? C311 C312 C313 C314 -68.1(19) . . . . ? O305 N301 S301 O301 56.1(11) . . . . ? S302 N301 S301 O301 177.9(9) . . . . ? O305 N301 S301 O302 -178.9(9) . . . . ? S302 N301 S301 O302 -57.0(10) . . . . ? O305 N301 S301 C301 -65.8(10) . . . . ? S302 N301 S301 C301 56.0(10) . . . . ? C302 C301 S301 O301 35.8(13) . . . . ? C306 C301 S301 O301 -150.8(11) . . . . ? C302 C301 S301 O302 -93.5(11) . . . . ? C306 C301 S301 O302 79.9(12) . . . . ? C302 C301 S301 N301 156.7(10) . . . . ? C306 C301 S301 N301 -29.9(12) . . . . ? O305 N301 S302 O304 179.9(9) . . . . ? S301 N301 S302 O304 62.0(10) . . . . ? O305 N301 S302 O303 -52.8(10) . . . . ? S301 N301 S302 O303 -170.7(8) . . . . ? O305 N301 S302 C310 63.3(10) . . . . ? S301 N301 S302 C310 -54.6(10) . . . . ? C309 C310 S302 O304 89.9(11) . . . . ? C306 C310 S302 O304 -87.8(11) . . . . ? C309 C310 S302 O303 -43.1(12) . . . . ? C306 C310 S302 O303 139.2(11) . . . . ? C309 C310 S302 N301 -154.7(9) . . . . ? C306 C310 S302 N301 27.6(11) . . . . ? 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 O5 H5 O401 0.84 2.13 2.560(13) 111.4 1_545 O205 H205 O201 0.84 2.31 2.811(19) 118.7 . O305 H305 O301 0.84 2.37 2.800(17) 112.0 . O35' H35' O501 0.84 2.04 2.58(5) 121.1 1_655 O35' H35' O33' 0.84 2.55 2.85(6) 102.3 . O401 H41A O34' 0.880(10) 2.42(13) 3.01(3) 125(12) 1_455 O401 H41B O104 0.881(10) 2.08(8) 2.842(12) 145(12) 1_465 O501 H51B O101 0.879(10) 2.59(9) 3.172(13) 124(9) 1_455 O601 H61A O4 0.880(10) 2.29(9) 2.997(12) 137(11) . O601 H61B O24' 0.880(10) 2.24(12) 2.88(3) 130(13) . O601 H61B O2 0.880(10) 2.57(13) 3.103(13) 120(12) . O701 H71A O32' 0.879(10) 2.46(7) 3.21(4) 144(9) 1_455 O701 H71B O1 0.878(10) 2.11(4) 2.950(12) 161(10) 1_565 _diffrn_measured_fraction_theta_max 0.905 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.905 _refine_diff_density_max 1.068 _refine_diff_density_min -0.650 _refine_diff_density_rms 0.122 #============================================================================== data_6.H2O _database_code_depnum_ccdc_archive 'CCDC 798810' #TrackingRef 'X-rays.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-hydroxy-O-benzenedisulfonimide monohydrate ; _chemical_name_common 'N-hydroxy-O-benzenedisulfonimide monohydrate' _chemical_melting_point ? _chemical_formula_moiety 'C6 H5 N O5 S2, H2 O' _chemical_formula_sum 'C6 H7 N O6 S2' _chemical_formula_weight 253.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2877(3) _cell_length_b 8.1680(3) _cell_length_c 8.3571(2) _cell_angle_alpha 93.740(2) _cell_angle_beta 107.823(2) _cell_angle_gamma 92.785(2) _cell_volume 471.35(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7224 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.784 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 260 _exptl_absorpt_coefficient_mu 0.574 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9138 _exptl_absorpt_correction_T_max 0.9886 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 8339 reflections reduced R(int) from 0.1005 to 0.0449 Ratio of minimum to maximum apparent transmission: 0.907589 The given Tmin and Tmax were generated using the SHELX SIZE command. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8728 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 27.67 _reflns_number_total 2171 _reflns_number_gt 1911 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ; Sir2004 (Burla, M.C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R., 2005) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0235P)^2^+0.7379P] 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 2171 _refine_ls_number_parameters 145 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.0918 _refine_ls_wR_factor_gt 0.0871 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1791(3) 0.2794(3) 0.4204(3) 0.0161(4) Uani 1 1 d . . . C2 C 0.2049(3) 0.3216(3) 0.5893(3) 0.0190(4) Uani 1 1 d . . . H2 H 0.1872 0.2416 0.6619 0.023 Uiso 1 1 calc R . . C3 C 0.2579(3) 0.4855(3) 0.6487(3) 0.0202(5) Uani 1 1 d . . . H3 H 0.2773 0.5180 0.7643 0.024 Uiso 1 1 calc R . . C4 C 0.2830(3) 0.6030(3) 0.5422(3) 0.0184(4) Uani 1 1 d . . . H4 H 0.3175 0.7143 0.5861 0.022 Uiso 1 1 calc R . . C5 C 0.2583(3) 0.5600(3) 0.3727(3) 0.0161(4) Uani 1 1 d . . . H5 H 0.2765 0.6397 0.3000 0.019 Uiso 1 1 calc R . . C6 C 0.2060(3) 0.3965(3) 0.3140(3) 0.0147(4) Uani 1 1 d . . . N1 N 0.1985(3) 0.1108(2) 0.1503(2) 0.0172(4) Uani 1 1 d . . . O1 O 0.1956(3) -0.0455(2) 0.4062(2) 0.0335(5) Uani 1 1 d . . . O2 O -0.1032(3) 0.0693(2) 0.2382(2) 0.0268(4) Uani 1 1 d . . . O3 O 0.3125(2) 0.36793(19) 0.0375(2) 0.0217(4) Uani 1 1 d . . . O4 O -0.0319(2) 0.3155(2) 0.0084(2) 0.0215(4) Uani 1 1 d . . . O5 O 0.4018(2) 0.1021(2) 0.2187(2) 0.0244(4) Uani 1 1 d . . . H5A H 0.4342 0.0144 0.1800 0.037 Uiso 1 1 calc R . . S1 S 0.10169(9) 0.08238(6) 0.31363(7) 0.01967(15) Uani 1 1 d . . . S2 S 0.16589(8) 0.31202(6) 0.10530(6) 0.01549(14) Uani 1 1 d . . . O101 O 0.4193(3) 0.8095(2) 0.0885(2) 0.0242(4) Uani 1 1 d D . . H11A H 0.498(4) 0.778(4) 0.036(4) 0.054(11) Uiso 1 1 d D . . H11B H 0.306(3) 0.783(4) 0.022(4) 0.051(10) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0157(10) 0.0141(10) 0.0182(10) 0.0015(8) 0.0049(8) 0.0013(8) C2 0.0231(12) 0.0187(11) 0.0160(10) 0.0027(8) 0.0071(9) 0.0004(9) C3 0.0190(11) 0.0237(11) 0.0176(11) -0.0013(9) 0.0058(9) 0.0018(9) C4 0.0177(11) 0.0144(10) 0.0215(11) -0.0020(8) 0.0045(9) 0.0023(8) C5 0.0152(10) 0.0145(10) 0.0186(11) 0.0028(8) 0.0049(8) 0.0016(8) C6 0.0144(10) 0.0160(10) 0.0141(10) 0.0004(8) 0.0048(8) 0.0033(8) N1 0.0175(9) 0.0150(9) 0.0192(9) -0.0005(7) 0.0062(7) 0.0015(7) O1 0.0574(13) 0.0176(8) 0.0253(9) 0.0071(7) 0.0112(9) 0.0047(8) O2 0.0274(9) 0.0275(9) 0.0263(9) -0.0042(7) 0.0131(7) -0.0110(7) O3 0.0251(9) 0.0217(8) 0.0219(8) 0.0014(6) 0.0131(7) -0.0008(7) O4 0.0199(8) 0.0230(8) 0.0194(8) 0.0047(6) 0.0024(6) 0.0000(6) O5 0.0180(8) 0.0197(8) 0.0325(9) -0.0042(7) 0.0043(7) 0.0050(6) S1 0.0288(3) 0.0131(3) 0.0177(3) 0.00064(19) 0.0088(2) -0.0025(2) S2 0.0180(3) 0.0154(3) 0.0138(3) 0.00155(19) 0.0060(2) 0.00073(19) O101 0.0187(9) 0.0232(9) 0.0317(10) -0.0036(7) 0.0103(7) 0.0025(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.383(3) . ? C1 C6 1.395(3) . ? C1 S1 1.766(2) . ? C2 C3 1.391(3) . ? C2 H2 0.9500 . ? C3 C4 1.393(3) . ? C3 H3 0.9500 . ? C4 C5 1.391(3) . ? C4 H4 0.9500 . ? C5 C6 1.386(3) . ? C5 H5 0.9500 . ? C6 S2 1.764(2) . ? N1 O5 1.422(2) . ? N1 S2 1.7215(19) . ? N1 S1 1.7411(19) . ? O1 S1 1.4174(18) . ? O2 S1 1.4273(19) . ? O3 S2 1.4242(16) . ? O4 S2 1.4238(16) . ? O5 H5A 0.8400 . ? O101 H11A 0.863(18) . ? O101 H11B 0.854(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 121.32(19) . . ? C2 C1 S1 125.89(17) . . ? C6 C1 S1 112.74(16) . . ? C1 C2 C3 117.4(2) . . ? C1 C2 H2 121.3 . . ? C3 C2 H2 121.3 . . ? C2 C3 C4 121.4(2) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 121.1(2) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C6 C5 C4 117.43(19) . . ? C6 C5 H5 121.3 . . ? C4 C5 H5 121.3 . . ? C5 C6 C1 121.37(19) . . ? C5 C6 S2 125.97(16) . . ? C1 C6 S2 112.66(15) . . ? O5 N1 S2 105.51(13) . . ? O5 N1 S1 106.77(13) . . ? S2 N1 S1 105.61(10) . . ? N1 O5 H5A 109.5 . . ? O1 S1 O2 120.33(11) . . ? O1 S1 N1 108.27(11) . . ? O2 S1 N1 106.00(10) . . ? O1 S1 C1 112.81(11) . . ? O2 S1 C1 110.14(10) . . ? N1 S1 C1 96.27(9) . . ? O4 S2 O3 119.48(10) . . ? O4 S2 N1 105.93(9) . . ? O3 S2 N1 108.62(10) . . ? O4 S2 C6 110.78(10) . . ? O3 S2 C6 112.18(10) . . ? N1 S2 C6 97.27(9) . . ? H11A O101 H11B 106(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 C6 C1 C2 C3 0.3(3) . . . . ? S1 C1 C2 C3 -176.96(17) . . . . ? C1 C2 C3 C4 0.3(3) . . . . ? C2 C3 C4 C5 -0.8(3) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C4 C5 C6 C1 0.0(3) . . . . ? C4 C5 C6 S2 179.88(16) . . . . ? C2 C1 C6 C5 -0.5(3) . . . . ? S1 C1 C6 C5 177.10(17) . . . . ? C2 C1 C6 S2 179.61(18) . . . . ? S1 C1 C6 S2 -2.8(2) . . . . ? O5 N1 S1 O1 -42.00(15) . . . . ? S2 N1 S1 O1 -153.97(11) . . . . ? O5 N1 S1 O2 -172.38(13) . . . . ? S2 N1 S1 O2 75.65(12) . . . . ? O5 N1 S1 C1 74.55(14) . . . . ? S2 N1 S1 C1 -37.42(11) . . . . ? C2 C1 S1 O1 -44.5(2) . . . . ? C6 C1 S1 O1 137.96(17) . . . . ? C2 C1 S1 O2 93.0(2) . . . . ? C6 C1 S1 O2 -84.51(18) . . . . ? C2 C1 S1 N1 -157.4(2) . . . . ? C6 C1 S1 N1 25.11(18) . . . . ? O5 N1 S2 O4 169.36(13) . . . . ? S1 N1 S2 O4 -77.79(11) . . . . ? O5 N1 S2 O3 39.85(15) . . . . ? S1 N1 S2 O3 152.70(10) . . . . ? O5 N1 S2 C6 -76.54(14) . . . . ? S1 N1 S2 C6 36.31(11) . . . . ? C5 C6 S2 O4 -90.9(2) . . . . ? C1 C6 S2 O4 88.95(17) . . . . ? C5 C6 S2 O3 45.4(2) . . . . ? C1 C6 S2 O3 -134.74(16) . . . . ? C5 C6 S2 N1 158.95(19) . . . . ? C1 C6 S2 N1 -21.20(18) . . . . ? 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 O5 H5A O101 0.84 1.78 2.585(2) 160.6 1_545 O101 H11A O3 0.863(18) 2.07(2) 2.892(2) 159(3) 2_665 O101 H11B O4 0.854(18) 2.05(2) 2.807(2) 148(3) 2_565 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.67 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.383 _refine_diff_density_min -0.566 _refine_diff_density_rms 0.081 #===================================END