#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/92/2019220.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2019220
loop_
_publ_author_name
'Tatum, Natalie J.'
'Villemagne, Baptiste'
'Willand, Nicolas'
'Deprez, Benoit'
'Liebeschuetz, John W.'
'Baulard, Alain R.'
'Pohl, Ehmke'
_publ_section_title
;
 Structural and docking studies of potent ethionamide boosters
;
_journal_coeditor_code           FM3013
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1243
_journal_page_last               1250
_journal_paper_doi               10.1107/S0108270113028126
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C14 H14 N4 O2 S'
_chemical_formula_moiety         'C14 H14 N4 O2 S'
_chemical_formula_sum            'C14 H14 N4 O2 S'
_chemical_formula_weight         302.35
_chemical_name_systematic
3-Oxo-3-{4-[3-(thiophen-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}propanenitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
  Olex2 1.1
  (compiled 2010.09.30 svn.r1450, GUI svn.r3284)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.882(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.834(2)
_cell_length_b                   16.923(3)
_cell_length_c                   12.531(2)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    99.8
_cell_measurement_theta_max      66.52
_cell_measurement_theta_min      3.65
_cell_volume                     1400.6(5)
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.8
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker MicroStar'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'HELIOS mirror system'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54188
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23371
_diffrn_reflns_theta_full        66.64
_diffrn_reflns_theta_max         66.64
_diffrn_reflns_theta_min         4.49
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.153
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.393
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.175
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0316
_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/[σ²(Fo²)+(0.0490P)²+0.8611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.1003
_reflns_number_gt                2413
_reflns_number_total             2429
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fm3013.cif
_cod_data_source_block           313ii_0m
_cod_database_code               2019220
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 0.27479(6) 0.31144(3) 0.22476(4) 0.02569(16) Uani d . 1 1
O O2 -0.00277(17) 0.43766(7) -0.09192(9) 0.0205(3) Uani d . 1 1
O O1 -1.08755(18) 0.47624(7) -0.37582(10) 0.0229(3) Uani d . 1 1
N N2 0.1140(2) 0.39798(9) 0.00272(11) 0.0212(3) Uani d . 1 1
N N1 -0.7480(2) 0.45847(9) -0.34241(11) 0.0200(3) Uani d . 1 1
N N3 -0.2216(2) 0.38676(8) -0.00780(11) 0.0191(3) Uani d . 1 1
C C9 -0.1072(3) 0.28747(10) 0.19892(13) 0.0206(4) Uani d . 1 1
H H9 -0.2501 0.2882 0.1705 0.025 Uiso calc R 1 1
C C12 -0.9412(3) 0.44142(10) -0.39353(13) 0.0190(4) Uani d . 1 1
C C7 -0.0240(3) 0.36966(9) 0.04803(13) 0.0184(4) Uani d . 1 1
C C6 -0.1987(2) 0.42765(9) -0.09150(13) 0.0175(3) Uani d . 1 1
N N4 -1.3506(2) 0.32975(10) -0.54264(13) 0.0290(4) Uani d . 1 1
C C2 -0.5429(2) 0.48936(10) -0.15440(13) 0.0195(4) Uani d . 1 1
H H2A -0.6010 0.4458 -0.1195 0.023 Uiso calc R 1 1
H H2B -0.5046 0.5326 -0.0998 0.023 Uiso calc R 1 1
C C3 -0.3544(2) 0.45975(10) -0.18700(13) 0.0183(4) Uani d . 1 1
H H3 -0.2939 0.5051 -0.2185 0.022 Uiso calc R 1 1
C C1 -0.7011(3) 0.51922(10) -0.25546(14) 0.0204(4) Uani d . 1 1
H H1A -0.8262 0.5336 -0.2340 0.024 Uiso calc R 1 1
H H1B -0.6497 0.5673 -0.2843 0.024 Uiso calc R 1 1
C C13 -0.9730(3) 0.37381(10) -0.47758(14) 0.0213(4) Uani d . 1 1
H H13A -0.9268 0.3907 -0.5427 0.026 Uiso calc R 1 1
H H13B -0.8905 0.3277 -0.4441 0.026 Uiso calc R 1 1
C C5 -0.5705(3) 0.42900(11) -0.37528(14) 0.0218(4) Uani d . 1 1
H H5A -0.5090 0.4726 -0.4082 0.026 Uiso calc R 1 1
H H5B -0.6127 0.3872 -0.4319 0.026 Uiso calc R 1 1
C C8 0.0269(3) 0.32454(10) 0.14981(14) 0.0198(4) Uani d . 1 1
C C14 -1.1862(3) 0.35065(10) -0.51288(14) 0.0225(4) Uani d . 1 1
C C10 -0.0041(3) 0.24788(10) 0.29772(15) 0.0244(4) Uani d . 1 1
H H10 -0.0717 0.2190 0.3426 0.029 Uiso calc R 1 1
C C4 -0.4153(2) 0.39576(10) -0.27644(14) 0.0198(4) Uani d . 1 1
H H4A -0.2944 0.3778 -0.2993 0.024 Uiso calc R 1 1
H H4B -0.4732 0.3497 -0.2465 0.024 Uiso calc R 1 1
C C11 0.1995(3) 0.25555(10) 0.32126(15) 0.0261(4) Uani d . 1 1
H H11 0.2903 0.2326 0.3840 0.031 Uiso calc R 1 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C11 S1 C8 91.39(9)
C6 O2 N2 106.43(12)
C7 N2 O2 102.89(13)
C12 N1 C1 120.23(14)
C12 N1 C5 125.21(14)
C5 N1 C1 114.04(13)
C6 N3 C7 102.46(14)
C8 C9 C10 111.40(16)
O1 C12 N1 123.86(16)
O1 C12 C13 120.22(15)
N1 C12 C13 115.92(14)
N2 C7 N3 114.97(15)
N2 C7 C8 122.50(16)
N3 C7 C8 122.52(15)
O2 C6 C3 117.18(14)
N3 C6 O2 113.25(14)
N3 C6 C3 129.46(15)
C1 C2 C3 110.63(13)
C6 C3 C2 112.48(13)
C6 C3 C4 109.49(13)
C2 C3 C4 109.63(13)
N1 C1 C2 110.88(13)
C14 C13 C12 111.25(14)
N1 C5 C4 110.62(13)
C9 C8 S1 111.73(13)
C9 C8 C7 126.54(16)
C7 C8 S1 121.73(13)
N4 C14 C13 177.06(19)
C11 C10 C9 113.31(16)
C5 C4 C3 109.62(14)
C10 C11 S1 112.16(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C8 1.7273(18)
S1 C11 1.7149(19)
O2 N2 1.4170(18)
O2 C6 1.351(2)
O1 C12 1.229(2)
N2 C7 1.310(2)
N1 C12 1.343(2)
N1 C1 1.472(2)
N1 C5 1.465(2)
N3 C7 1.383(2)
N3 C6 1.299(2)
C9 C8 1.379(2)
C9 C10 1.425(2)
C12 C13 1.532(2)
C7 C8 1.450(2)
C6 C3 1.485(2)
N4 C14 1.145(2)
C2 C3 1.532(2)
C2 C1 1.525(2)
C3 C4 1.537(2)
C13 C14 1.463(2)
C5 C4 1.517(2)
C10 C11 1.353(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 24804431
