Thiolates Chemically Induce Redox Activation of BTZ043 and Related Potent Nitroaromatic Anti-Tuberculosis Agents
Rohit Tiwari; Garrett C. Moraski; Viktor Krchňák; Patricia A. Miller; Mariangelli Colon-Martinez; Eliza Herrero; Allen G. Oliver; Marvin J. Miller; Journal of the American Chemical Society 135 (2013) 3539–3549; doi:10.1021/ja311058q

data_4119406
_publ_contact_author_address     '347 NSH'
_publ_contact_author_email       tiwari.4@nd.edu
_publ_contact_author_name        'Rohit Tiwari'
_publ_section_title
;
 Thiolates Chemically Induce Redox Activation of BTZ043 and Related Potent
 Nitroaromatic Anti-Tuberculosis Agents
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3539
_journal_page_last               3549
_journal_paper_doi               10.1021/ja311058q
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C16 H18 N4 O6'
_chemical_formula_sum            'C16 H18 N4 O6'
_chemical_formula_weight         362.34
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 90.6040(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.66900(10)
_cell_length_b                   8.06660(10)
_cell_length_c                   20.7830(3)
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      71.25
_cell_measurement_theta_min      4.25
_cell_volume                     1620.90(4)
_computing_cell_refinement       'Bruker SAINT v8.18C'
_computing_data_collection       'Bruker APEX-II v2012-2.0'
_computing_data_reduction        'Bruker SAINT v8.18C'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_monochromator  'MONTEL Multi-layer'
_diffrn_radiation_source         'Incoatec micro-focus'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0171
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25993
_diffrn_reflns_theta_full        71.36
_diffrn_reflns_theta_max         71.36
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.979
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_correction_T_min  0.9247
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS, Sheldrick, 2008'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         5760
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0685P)^2^+0.5680P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1116
_reflns_number_gt                5559
_reflns_number_total             5760
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja311058q_si_002_2.cif
_cod_data_source_block           nd1237(compound31)
_cod_database_code               4119406