data_publication_text _publ_requested_journal ACS Med.Chem.Lett. _publ_contact_author_name 'Professor Shahriar Mobashery' _publ_contact_author_address ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; _publ_contact_author_email mobashery@nd.edu _publ_contact_author_phone 1(574)6312933 _publ_contact_author_fax 1(574)6316652 loop_ _publ_author_name _publ_author_address 'Lee, Mijoon' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Ikejiri, Masahiro' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Klimpel,Dennis' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Toth, Marta' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Expahbodi, Mana' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Hesek, Dusan' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Forbes, Christopher' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Noll, Bruce C.' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Chang, Mayland' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; data_compound_40 # local file ID: data_dh39_1_0ma _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C15 H16 N2 O5 S3' _chemical_formula_sum 'C15 H16 N2 O5 S3' _chemical_compound_source synthesized _chemical_melting_point ? _exptl_crystal_description plate _exptl_crystal_colour 'clear colorless' _diffrn_ambient_temperature 100(2) _chemical_formula_weight 400.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_int_tables_number 2 _chemical_absolute_configuration . loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.7099(4) _cell_length_b 10.7256(6) _cell_length_c 15.2849(12) _cell_angle_alpha 107.324(5) _cell_angle_beta 95.601(5) _cell_angle_gamma 99.714(4) _cell_volume 869.86(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4498 _cell_measurement_theta_min 3.066 _cell_measurement_theta_max 68.230 _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.529 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 4.170 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.72 _exptl_absorpt_correction_T_max 0.88 _exptl_absorpt_process_details 'Sheldrick, G. M. (2006). SADABS. University of G\"ottingen, Germany.' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Siemens KFFCU2K-90' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Apex CCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_reflns_number 8252 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 68.23 _reflns_number_total 2866 _reflns_number_gt 2694 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Bruker-Nonius AXS. (2007). APEX2 and SAINT. Bruker-Nonius AXS, Madison, Wisconsin, USA. CCDC. (2005). enCIFer. The Cambridge Crystallographic Data Centre, Cambridge, UK. Sheldrick, G. M. (2007). SADABS. University of G\"ottingen, Germany. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2007; Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material 'XCIF (Sheldrick, 2008)/enCIFer (CCDC, 2005)' _refine_special_details ; Disorder was found in the thiirane moiety. Two orientations are present for this ring. Site occupancies were refined together and the site occupancy for the major orientation was found to be 0.829(5). 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^)+(0.0525P)^2^+0.9120P] 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 2866 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.1004 _refine_ls_wR_factor_gt 0.0986 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.06113(10) 0.41049(5) 1.25767(4) 0.02019(17) Uani 1 1 d . . . S2 S -0.3606(3) 0.07661(9) 1.13650(7) 0.0371(4) Uani 0.829(5) 1 d P A 1 S2' S -0.451(2) 0.0431(10) 1.2176(9) 0.050(3) Uani 0.171(5) 1 d P A 2 S3 S 0.46384(10) 0.25154(6) 0.50911(4) 0.02110(17) Uani 1 1 d . . . N1 N 0.2727(3) 0.29574(19) 0.82512(13) 0.0212(4) Uani 1 1 d . . . N2 N 0.5428(3) 0.23785(19) 0.61141(13) 0.0213(4) Uani 1 1 d . . . H1N H 0.6948 0.2399 0.6299 0.026 Uiso 1 1 calc R . . O1 O -0.1093(3) 0.21047(17) 0.85003(11) 0.0260(4) Uani 1 1 d . . . O2 O 0.0334(3) 0.54814(17) 1.28982(11) 0.0276(4) Uani 1 1 d . . . O3 O 0.2807(3) 0.38068(18) 1.29274(11) 0.0274(4) Uani 1 1 d . . . O4 O 0.3071(3) 0.12975(17) 0.45160(12) 0.0323(4) Uani 1 1 d . . . O5 O 0.6862(3) 0.29668(17) 0.48076(11) 0.0268(4) Uani 1 1 d . . . C1 C 0.0639(4) 0.2114(2) 0.79309(15) 0.0204(5) Uani 1 1 d . . . C2 C -0.0051(4) 0.1250(2) 0.70262(16) 0.0217(5) Uani 1 1 d . . . H2 H -0.1565 0.0645 0.6841 0.026 Uiso 1 1 calc R . . C3 C 0.1535(4) 0.1302(2) 0.64073(16) 0.0218(5) Uani 1 1 d . . . H3 H 0.1151 0.0717 0.5786 0.026 Uiso 1 1 calc R . . C4 C 0.3712(4) 0.2227(2) 0.67098(16) 0.0194(5) Uani 1 1 d . . . C5 C 0.4227(4) 0.3010(2) 0.76350(16) 0.0205(5) Uani 1 1 d . . . H5 H 0.5733 0.3622 0.7845 0.025 Uiso 1 1 calc R . . C7 C -0.0484(4) 0.2637(2) 0.94564(16) 0.0224(5) Uani 1 1 d . . . C8 C -0.1944(4) 0.3443(2) 0.99099(16) 0.0235(5) Uani 1 1 d . . . H8 H -0.3197 0.3662 0.9565 0.028 Uiso 1 1 calc R . . C9 C -0.1560(4) 0.3922(2) 1.08676(16) 0.0229(5) Uani 1 1 d . . . H9 H -0.2527 0.4488 1.1188 0.027 Uiso 1 1 calc R . . C10 C 0.0253(4) 0.3569(2) 1.13556(15) 0.0208(5) Uani 1 1 d . . . C11 C 0.1703(5) 0.2755(3) 1.09011(17) 0.0295(6) Uani 1 1 d . . . H11 H 0.2926 0.2514 1.1245 0.035 Uiso 1 1 calc R . . C12 C 0.1348(5) 0.2301(3) 0.99435(17) 0.0299(6) Uani 1 1 d . . . H12 H 0.2353 0.1763 0.9622 0.036 Uiso 1 1 calc R . . C13 C -0.1876(4) 0.3164(2) 1.28681(17) 0.0261(5) Uani 1 1 d . A . H13A H -0.1794 0.3473 1.3551 0.031 Uiso 1 1 calc R . . H13B H -0.3376 0.3343 1.2594 0.031 Uiso 1 1 calc R . . C14 C -0.2002(5) 0.1694(3) 1.2547(2) 0.0355(6) Uani 1 1 d . . . H14 H -0.0564 0.1380 1.2760 0.043 Uiso 1 1 calc R A 1 C15 C -0.4440(17) 0.0834(7) 1.2487(5) 0.0360(17) Uani 0.829(5) 1 d P A 1 H15A H -0.5753 0.1303 1.2675 0.043 Uiso 0.829(5) 1 calc PR A 1 H15B H -0.4464 0.0024 1.2673 0.043 Uiso 0.829(5) 1 calc PR A 1 C15' C -0.221(7) 0.086(2) 1.150(2) 0.064(8) Uani 0.171(5) 1 d P A 2 H15C H -0.1075 0.0260 1.1331 0.077 Uiso 0.171(5) 1 calc PR A 2 H15D H -0.2648 0.1288 1.1032 0.077 Uiso 0.171(5) 1 calc PR A 2 C16 C 0.2972(4) 0.3783(3) 0.52819(18) 0.0268(5) Uani 1 1 d . . . H16A H 0.2567 0.3963 0.4700 0.040 Uiso 1 1 calc R . . H16B H 0.3931 0.4597 0.5747 0.040 Uiso 1 1 calc R . . H16C H 0.1489 0.3496 0.5506 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0161(3) 0.0265(3) 0.0147(3) 0.0043(2) 0.0030(2) -0.0005(2) S2 0.0460(9) 0.0224(5) 0.0366(5) 0.0009(3) 0.0157(5) 0.0006(5) S2' 0.026(3) 0.041(6) 0.088(9) 0.035(5) 0.005(4) -0.004(3) S3 0.0200(3) 0.0264(3) 0.0139(3) 0.0043(2) 0.0040(2) -0.0003(2) N1 0.0220(11) 0.0242(10) 0.0158(10) 0.0046(8) 0.0027(8) 0.0040(8) N2 0.0155(10) 0.0294(10) 0.0194(10) 0.0082(8) 0.0039(7) 0.0041(8) O1 0.0207(9) 0.0402(10) 0.0129(8) 0.0037(7) 0.0044(6) 0.0028(7) O2 0.0259(9) 0.0305(9) 0.0213(9) 0.0022(7) 0.0016(7) 0.0045(7) O3 0.0224(9) 0.0404(10) 0.0197(9) 0.0085(7) 0.0038(7) 0.0092(7) O4 0.0367(11) 0.0323(10) 0.0170(9) -0.0005(7) 0.0038(7) -0.0065(8) O5 0.0214(9) 0.0384(10) 0.0202(9) 0.0096(7) 0.0073(7) 0.0026(7) C1 0.0202(12) 0.0259(12) 0.0162(12) 0.0076(9) 0.0039(9) 0.0059(9) C2 0.0210(12) 0.0223(11) 0.0187(12) 0.0051(9) 0.0016(9) -0.0002(9) C3 0.0257(13) 0.0228(11) 0.0142(11) 0.0035(9) 0.0027(9) 0.0026(9) C4 0.0207(12) 0.0211(11) 0.0182(12) 0.0080(9) 0.0032(9) 0.0057(9) C5 0.0198(12) 0.0220(11) 0.0185(12) 0.0061(9) 0.0018(9) 0.0021(9) C7 0.0201(12) 0.0281(12) 0.0157(12) 0.0052(9) 0.0033(9) -0.0010(9) C8 0.0217(13) 0.0293(12) 0.0198(12) 0.0088(10) 0.0031(9) 0.0046(10) C9 0.0228(13) 0.0237(12) 0.0221(13) 0.0054(10) 0.0071(9) 0.0058(9) C10 0.0193(12) 0.0238(11) 0.0168(12) 0.0057(9) 0.0043(9) -0.0015(9) C11 0.0242(13) 0.0456(15) 0.0217(13) 0.0114(11) 0.0061(10) 0.0132(11) C12 0.0286(14) 0.0418(15) 0.0204(13) 0.0054(11) 0.0086(10) 0.0160(11) C13 0.0215(13) 0.0331(13) 0.0255(13) 0.0112(11) 0.0075(10) 0.0048(10) C14 0.0361(16) 0.0349(14) 0.0403(16) 0.0183(13) 0.0092(12) 0.0069(12) C15 0.038(3) 0.031(4) 0.045(4) 0.021(3) 0.016(3) 0.006(3) C15' 0.051(17) 0.039(12) 0.10(2) 0.022(12) 0.031(15) -0.016(12) C16 0.0206(12) 0.0370(14) 0.0264(13) 0.0161(11) 0.0049(10) 0.0047(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 S1 O3 1.4377(18) . ? S1 O2 1.4519(18) . ? S1 C10 1.761(2) . ? S1 C13 1.772(2) . ? S2 C15 1.808(8) . ? S2 C14 1.842(3) . ? S2' C14 1.714(11) . ? S2' C15' 1.83(3) . ? S3 O4 1.4311(18) . ? S3 O5 1.4349(17) . ? S3 N2 1.640(2) . ? S3 C16 1.759(3) . ? N1 C1 1.319(3) . ? N1 C5 1.341(3) . ? N2 C4 1.423(3) . ? N2 H1N 0.8800 . ? O1 C1 1.380(3) . ? O1 C7 1.385(3) . ? C1 C2 1.390(3) . ? C2 C3 1.378(3) . ? C2 H2 0.9500 . ? C3 C4 1.393(3) . ? C3 H3 0.9500 . ? C4 C5 1.386(3) . ? C5 H5 0.9500 . ? C7 C12 1.383(4) . ? C7 C8 1.386(3) . ? C8 C9 1.381(3) . ? C8 H8 0.9500 . ? C9 C10 1.386(3) . ? C9 H9 0.9500 . ? C10 C11 1.387(3) . ? C11 C12 1.380(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.492(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.512(9) . ? C14 C15' 1.56(3) . ? C14 H14 1.0000 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C15' H15C 0.9900 . ? C15' H15D 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 S1 O2 117.65(11) . . ? O3 S1 C10 108.64(11) . . ? O2 S1 C10 108.50(11) . . ? O3 S1 C13 109.70(11) . . ? O2 S1 C13 105.62(11) . . ? C10 S1 C13 106.15(12) . . ? C15 S2 C14 49.0(3) . . ? C14 S2' C15' 52.2(10) . . ? O4 S3 O5 119.31(10) . . ? O4 S3 N2 108.99(10) . . ? O5 S3 N2 104.78(10) . . ? O4 S3 C16 107.87(12) . . ? O5 S3 C16 109.25(11) . . ? N2 S3 C16 105.85(11) . . ? C1 N1 C5 116.3(2) . . ? C4 N2 S3 121.48(16) . . ? C4 N2 H1N 119.3 . . ? S3 N2 H1N 119.3 . . ? C1 O1 C7 121.06(18) . . ? N1 C1 O1 119.5(2) . . ? N1 C1 C2 125.0(2) . . ? O1 C1 C2 115.5(2) . . ? C3 C2 C1 117.8(2) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C2 C3 C4 118.8(2) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 118.1(2) . . ? C5 C4 N2 119.1(2) . . ? C3 C4 N2 122.8(2) . . ? N1 C5 C4 123.9(2) . . ? N1 C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? C12 C7 O1 122.2(2) . . ? C12 C7 C8 121.4(2) . . ? O1 C7 C8 116.2(2) . . ? C9 C8 C7 119.4(2) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C10 119.3(2) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C9 C10 C11 121.3(2) . . ? C9 C10 S1 118.87(17) . . ? C11 C10 S1 119.73(19) . . ? C12 C11 C10 119.3(2) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C11 C12 C7 119.4(2) . . ? C11 C12 H12 120.3 . . ? C7 C12 H12 120.3 . . ? C14 C13 S1 114.13(18) . . ? C14 C13 H13A 108.7 . . ? S1 C13 H13A 108.7 . . ? C14 C13 H13B 108.7 . . ? S1 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C13 C14 C15 115.5(4) . . ? C13 C14 C15' 122.6(11) . . ? C15 C14 C15' 84.6(11) . . ? C13 C14 S2' 128.2(4) . . ? C15' C14 S2' 67.8(11) . . ? C13 C14 S2 116.3(2) . . ? C15 C14 S2 64.3(3) . . ? S2' C14 S2 49.9(4) . . ? C13 C14 H14 116.8 . . ? C15 C14 H14 116.8 . . ? C15' C14 H14 95.3 . . ? S2' C14 H14 111.6 . . ? S2 C14 H14 116.8 . . ? C14 C15 S2 66.7(3) . . ? C14 C15 H15A 117.0 . . ? S2 C15 H15A 117.0 . . ? C14 C15 H15B 117.0 . . ? S2 C15 H15B 117.0 . . ? H15A C15 H15B 114.1 . . ? C14 C15' S2' 60.0(9) . . ? C14 C15' H15C 117.8 . . ? S2' C15' H15C 117.8 . . ? C14 C15' H15D 117.8 . . ? S2' C15' H15D 117.8 . . ? H15C C15' H15D 114.9 . . ? S3 C16 H16A 109.5 . . ? S3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? S3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_distance_DA _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N2 H1N 0.880 2.420 120 2.958(3) O2 2_667 y _diffrn_measured_fraction_theta_max 0.902 _diffrn_reflns_theta_full 68.23 _diffrn_measured_fraction_theta_full 0.902 _refine_diff_density_max 0.581 _refine_diff_density_min -0.500 _refine_diff_density_rms 0.060