Thioamide hydroxypyrothiones supersede amide hydroxypyrothiones in potency against anthrax lethal factor.
Agrawal, Arpita; de Oliveira, César Augusto F; Cheng, Yuhui; Jacobsen, Jennifer A.; McCammon, J. Andrew; Cohen, Seth M.; Journal of medicinal chemistry 52 (2009) 1063–1074; doi:10.1021/jm8013212

data_1503662
_publ_section_title
;
 Thioamide hydroxypyrothiones supersede amide hydroxypyrothiones in
 potency against anthrax lethal factor.
;
_journal_issue                   4
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              1063
_journal_page_last               1074
_journal_paper_doi               10.1021/jm8013212
_journal_volume                  52
_journal_year                    2009
_chemical_formula_moiety         'C14 H13 N O3 S2'
_chemical_formula_sum            'C14 H13 N O3 S2'
_chemical_formula_weight         307.37
_chemical_name_common            aa_py4os2
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.516(6)
_cell_length_b                   9.108(4)
_cell_length_c                   22.558(9)
_cell_measurement_reflns_used    18847
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.58
_cell_measurement_theta_min      2.84
_cell_volume                     2777(2)
_computing_cell_refinement       SAINT
_computing_data_collection       'Apex2 v.1.0-2.1 (Bruker, 2006)'
_computing_data_reduction        'SAINT v7.34A (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL 5.1 (Sheldrick, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Apex'
_diffrn_measurement_method       \w\f
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_sigmaI/netI    0.0757
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17598
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.65
_diffrn_reflns_theta_min         1.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.389
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.10 (Sheldrick, 2004)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.50(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5139
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.7874P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1096
_reflns_number_gt                4726
_reflns_number_total             5139
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jm8013212_si_001.cif
_cod_data_source_block           aa_py4os2
_cod_database_code               1503662