Ethionamide biomimetic activation and an unprecedented mechanism for its conversion into active and non-active metabolites.
Laborde, Julie; Deraeve, Céline; Duhayon, Carine; Pratviel, Geneviève; Bernardes-Génisson, Vania; Organic & biomolecular chemistry 14 (2016) 8848–8858; doi:10.1039/c6ob01561a

data_7155263
_publ_section_title
;
 Ethionamide biomimetic activation and an unprecedented mechanism for its
 conversion into active and non-active metabolites.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8848
_journal_page_last               8858
_journal_paper_doi               10.1039/c6ob01561a
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C8 H10 N2 O1 S1'
_chemical_formula_sum            'C8 H10 N2 O S'
_chemical_formula_weight         182.25
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2016-07-20 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.149(11)
_cell_angle_beta                 100.435(12)
_cell_angle_gamma                104.134(11)
_cell_formula_units_Z            4
_cell_length_a                   8.2425(11)
_cell_length_b                   8.4394(10)
_cell_length_c                   13.236(2)
_cell_measurement_reflns_used    5724
_cell_measurement_temperature    180
_cell_measurement_theta_max      71
_cell_measurement_theta_min      5
_cell_volume                     877.0(2)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12822
_diffrn_reflns_theta_full        69.057
_diffrn_reflns_theta_max         70.466
_diffrn_reflns_theta_min         3.399
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.894
_exptl_absorpt_correction_T_max  0.79
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       planar
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0588
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2741
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.0012226
_refine_ls_shift/su_mean         0.0000493
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 11.3 -0.914 9.69 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0428
_refine_ls_wR_factor_gt          0.0425
_refine_ls_wR_factor_ref         0.0425
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2868
_reflns_number_total             3331
_reflns_threshold_expression     I>2.0\s(I)
_oxford_refine_ls_r_factor_ref   0.0340
_oxford_reflns_number_all        3317
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            c6ob01561a2.cif
_cod_data_source_block           1
_cod_depositor_comments
;Adding full bibliography for 7155263.cif.

 Adding full bibliography for 7155263.cif.
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C8 H10 N2 O1 S1'
_cod_database_code               7155263
_iucr_refine_instructions_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE N   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) H   ( 123,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE N   (  30,X'S) H   ( 301,X'S) H   ( 302,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) H   ( 312,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) H   ( 322,X'S) H   ( 323,X'S) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;