#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/53/2225309.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_2225309
loop_
_publ_author_name
'Dolzhenko, Anton V.'
'Tan, Geok Kheng'
'Koh, Lip Lin'
'Dolzhenko, Anna V.'
'Chui, Wai Keung'
_publ_section_title
N-Carbethoxy-N'-[3-(4-methylphenyl)-1H-1,2,4-triazol-5-yl]thiourea
_journal_coeditor_code           KP2249
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o549
_journal_page_last               o550
_journal_paper_doi               10.1107/S1600536810004289
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H15 N5 O2 S'
_chemical_formula_moiety         'C13 H15 N5 O2 S'
_chemical_formula_sum            'C13 H15 N5 O2 S'
_chemical_formula_weight         305.36
_chemical_melting_point          489
_chemical_name_systematic
;
ethyl 
({[3-(4-methylphenyl)-1H-1,2,4-triazol-5-yl]amino}carbonothioyl)carbamate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.7800(10)
_cell_angle_beta                 99.4250(10)
_cell_angle_gamma                101.2790(10)
_cell_formula_units_Z            2
_cell_length_a                   6.8430(5)
_cell_length_b                   8.7789(6)
_cell_length_c                   12.2563(9)
_cell_measurement_reflns_used    6864
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.37
_cell_volume                     711.52(9)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9015
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.69
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.9446
_exptl_absorpt_correction_T_min  0.8773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.307
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0356
_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/[σ²(Fo²)+(0.0529P)²+0.3280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0953
_reflns_number_gt                3088
_reflns_number_total             3243
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2249.cif
_cod_data_source_block           I
_cod_database_code               2225309
_cod_database_fobs_code          2225309
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_disorder_assembly
_atom_site_disorder_group
S S1 0.23286(5) 0.36065(4) 0.52820(2) 0.01721(11) Uani d . 1 . .
O O1 0.17169(14) 0.49382(11) 0.16661(8) 0.0193(2) Uani d . 1 . .
O O2 -0.10045(14) 0.57606(10) 0.20980(8) 0.0174(2) Uani d . 1 . .
N N1 0.62121(16) 0.25023(12) 0.28575(9) 0.0155(2) Uani d . 1 . .
N N2 0.51358(16) 0.16832(13) 0.43785(9) 0.0162(2) Uani d . 1 . .
H H2N 0.440(3) 0.145(2) 0.4885(16) 0.029(5) Uiso d . 1 . .
N N3 0.65581(16) 0.08284(13) 0.42368(9) 0.0173(2) Uani d . 1 . .
N N4 0.35689(16) 0.35967(12) 0.33186(9) 0.0156(2) Uani d . 1 . .
H H4N 0.343(3) 0.390(2) 0.2676(16) 0.024(4) Uiso d . 1 . .
N N5 0.09899(17) 0.48816(13) 0.34439(9) 0.0163(2) Uani d . 1 . .
H H5N 0.016(3) 0.512(2) 0.3841(15) 0.022(4) Uiso d . 1 . .
C C1 1.3339(2) -0.07535(17) 0.13315(12) 0.0239(3) Uani d . 1 . .
H H1A 1.4199 -0.1231 0.1888 0.036 Uiso calc R 1 . .
H H1B 1.4169 0.0132 0.1036 0.036 Uiso calc R 1 . .
H H1C 1.2688 -0.1521 0.0728 0.036 Uiso calc R 1 . .
C C2 1.17417(19) -0.02005(15) 0.18576(11) 0.0180(3) Uani d . 1 . .
C C3 1.0630(2) 0.08361(15) 0.13251(11) 0.0184(3) Uani d . 1 . .
H H3 1.0898 0.1204 0.0628 0.022 Uiso calc R 1 . .
C C4 0.91420(19) 0.13361(14) 0.17991(11) 0.0169(3) Uani d . 1 . .
H H4 0.8391 0.2029 0.1420 0.020 Uiso calc R 1 . .
C C5 0.87416(18) 0.08280(14) 0.28277(10) 0.0149(2) Uani d . 1 . .
C C6 0.98549(19) -0.01994(14) 0.33704(11) 0.0169(3) Uani d . 1 . .
H H6 0.9604 -0.0554 0.4073 0.020 Uiso calc R 1 . .
C C7 1.13279(19) -0.07028(15) 0.28828(11) 0.0180(3) Uani d . 1 . .
H H7 1.2069 -0.1405 0.3258 0.022 Uiso calc R 1 . .
C C8 0.71732(18) 0.13779(14) 0.33214(10) 0.0144(2) Uani d . 1 . .
C C9 0.49501(18) 0.26348(14) 0.35425(10) 0.0143(2) Uani d . 1 . .
C C10 0.23405(18) 0.40227(14) 0.39616(10) 0.0144(2) Uani d . 1 . .
C C11 0.06534(19) 0.51753(14) 0.23292(11) 0.0156(2) Uani d . 1 . .
C C12 -0.1632(2) 0.59864(16) 0.09263(11) 0.0197(3) Uani d . 1 . .
H H12A -0.2036 0.4972 0.0505 0.024 Uiso calc R 1 . .
H H12B -0.0510 0.6633 0.0622 0.024 Uiso calc R 1 . .
C C13 -0.3400(2) 0.67920(17) 0.08463(12) 0.0234(3) Uani d . 1 . .
H H13A -0.4464 0.6170 0.1192 0.035 Uiso calc R 1 . .
H H13B -0.3926 0.6911 0.0066 0.035 Uiso calc R 1 . .
H H13C -0.2958 0.7819 0.1229 0.035 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 O2 C12 . . 114.69(10) ?
C9 N1 C8 . . 102.36(10) ?
C9 N2 N3 . . 109.09(10) ?
C9 N2 H2N . . 130.3(12) ?
N3 N2 H2N . . 119.7(12) ?
C8 N3 N2 . . 102.49(10) ?
C10 N4 C9 . . 129.41(11) ?
C10 N4 H4N . . 116.0(12) ?
C9 N4 H4N . . 114.5(12) ?
C11 N5 C10 . . 126.49(11) ?
C11 N5 H5N . . 117.7(12) ?
C10 N5 H5N . . 115.0(12) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C7 C2 C3 . . 118.02(11) ?
C7 C2 C1 . . 121.23(12) ?
C3 C2 C1 . . 120.75(12) ?
C4 C3 C2 . . 121.03(12) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C3 C4 C5 . . 120.49(12) ?
C3 C4 H4 . . 119.8 ?
C5 C4 H4 . . 119.8 ?
C4 C5 C6 . . 118.90(11) ?
C4 C5 C8 . . 119.80(11) ?
C6 C5 C8 . . 121.30(11) ?
C7 C6 C5 . . 120.07(12) ?
C7 C6 H6 . . 120.0 ?
C5 C6 H6 . . 120.0 ?
C6 C7 C2 . . 121.48(12) ?
C6 C7 H7 . . 119.3 ?
C2 C7 H7 . . 119.3 ?
N3 C8 N1 . . 114.56(11) ?
N3 C8 C5 . . 123.37(11) ?
N1 C8 C5 . . 122.06(11) ?
N1 C9 N2 . . 111.46(11) ?
N1 C9 N4 . . 120.65(11) ?
N2 C9 N4 . . 127.77(11) ?
N4 C10 N5 . . 114.73(11) ?
N4 C10 S1 . . 125.77(9) ?
N5 C10 S1 . . 119.49(9) ?
O1 C11 O2 . . 125.35(12) ?
O1 C11 N5 . . 125.32(12) ?
O2 C11 N5 . . 109.33(11) ?
O2 C12 C13 . . 106.66(11) ?
O2 C12 H12A . . 110.4 ?
C13 C12 H12A . . 110.4 ?
O2 C12 H12B . . 110.4 ?
C13 C12 H12B . . 110.4 ?
H12A C12 H12B . . 108.6 ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C10 . 1.6649(13) ?
O1 C11 . 1.2173(16) ?
O2 C11 . 1.3260(15) ?
O2 C12 . 1.4578(15) ?
N1 C9 . 1.3184(16) ?
N1 C8 . 1.3701(15) ?
N2 C9 . 1.3364(16) ?
N2 N3 . 1.3704(14) ?
N2 H2N . 0.865(19) ?
N3 C8 . 1.3261(16) ?
N4 C10 . 1.3414(16) ?
N4 C9 . 1.3839(15) ?
N4 H4N . 0.830(19) ?
N5 C11 . 1.3840(16) ?
N5 C10 . 1.3853(16) ?
N5 H5N . 0.856(18) ?
C1 C2 . 1.5088(17) ?
C1 H1A . 0.9800 ?
C1 H1B . 0.9800 ?
C1 H1C . 0.9800 ?
C2 C7 . 1.3915(19) ?
C2 C3 . 1.3988(18) ?
C3 C4 . 1.3889(17) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.3943(17) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.3984(17) ?
C5 C8 . 1.4691(17) ?
C6 C7 . 1.3903(17) ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C12 C13 . 1.5067(18) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2N N3 2_656 0.865(19) 2.316(19) 2.9719(15) 132.8(16)
N2 H2N S1 . 0.865(19) 2.660(19) 3.1116(11) 113.8(15)
N4 H4N O1 . 0.830(19) 1.929(18) 2.6274(14) 141.2(17)
N5 H5N S1 2_566 0.856(18) 2.576(19) 3.4119(11) 165.7(16)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N2 N3 C8 . . . . 1.76(13) ?
C7 C2 C3 C4 . . . . -0.71(19) ?
C1 C2 C3 C4 . . . . 179.27(12) ?
C2 C3 C4 C5 . . . . 0.84(19) ?
C3 C4 C5 C6 . . . . -0.36(19) ?
C3 C4 C5 C8 . . . . 179.52(11) ?
C4 C5 C6 C7 . . . . -0.23(19) ?
C8 C5 C6 C7 . . . . 179.89(11) ?
C5 C6 C7 C2 . . . . 0.36(19) ?
C3 C2 C7 C6 . . . . 0.11(19) ?
C1 C2 C7 C6 . . . . -179.87(12) ?
N2 N3 C8 N1 . . . . -1.24(14) ?
N2 N3 C8 C5 . . . . 179.33(11) ?
C9 N1 C8 N3 . . . . 0.24(14) ?
C9 N1 C8 C5 . . . . 179.68(11) ?
C4 C5 C8 N3 . . . . 172.75(12) ?
C6 C5 C8 N3 . . . . -7.38(19) ?
C4 C5 C8 N1 . . . . -6.63(18) ?
C6 C5 C8 N1 . . . . 173.24(11) ?
C8 N1 C9 N2 . . . . 0.94(14) ?
C8 N1 C9 N4 . . . . -175.31(11) ?
N3 N2 C9 N1 . . . . -1.78(15) ?
N3 N2 C9 N4 . . . . 174.14(12) ?
C10 N4 C9 N1 . . . . -171.44(12) ?
C10 N4 C9 N2 . . . . 13.0(2) ?
C9 N4 C10 N5 . . . . -173.84(12) ?
C9 N4 C10 S1 . . . . 6.13(19) ?
C11 N5 C10 N4 . . . . 7.69(18) ?
C11 N5 C10 S1 . . . . -172.28(10) ?
C12 O2 C11 O1 . . . . 5.70(18) ?
C12 O2 C11 N5 . . . . -174.54(10) ?
C10 N5 C11 O1 . . . . -12.6(2) ?
C10 N5 C11 O2 . . . . 167.62(11) ?
C11 O2 C12 C13 . . . . -174.72(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744444
2 PubChem 90996102
