#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/49/2224966.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_2224966
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-phenyl-1H-1,2,4-triazol-5-yl)thiourea
_journal_coeditor_code           GW2076
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o425
_journal_paper_doi               10.1107/S1600536810002369
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H13 N5 O2 S'
_chemical_formula_moiety         'C12 H13 N5 O2 S'
_chemical_formula_sum            'C12 H13 N5 O2 S'
_chemical_formula_weight         291.33
_chemical_melting_point          454
_chemical_name_common
;
N-Carbethoxy-N'-(3-phenyl-1H-1,2,4-triazol-5-yl)thiourea
;
_chemical_name_systematic
;
ethyl N-[N-(3-phenyl-1H-1,2,4-triazol-5-
yl)carbamothioyl]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                91.8180(10)
_cell_angle_beta                 92.5850(10)
_cell_angle_gamma                101.0830(10)
_cell_formula_units_Z            2
_cell_length_a                   5.9929(3)
_cell_length_b                   9.4200(5)
_cell_length_c                   12.2000(7)
_cell_measurement_reflns_used    4121
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.71
_cell_volume                     674.62(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8943
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.67
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.9707
_exptl_absorpt_correction_T_min  0.8730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.203
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3092
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0399
_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)+(0.0557P)²+0.2404P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1019
_reflns_number_gt                2828
_reflns_number_total             3092
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gw2076.cif
_cod_data_source_block           I
_cod_database_code               2224966
_cod_database_fobs_code          2224966
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 0.26167(6) 0.64734(4) -0.02591(3) 0.02072(12) Uani d . 1 . .
O O1 0.58945(18) 0.44334(11) 0.28112(8) 0.0204(2) Uani d . 1 . .
O O2 0.31338(18) 0.55681(11) 0.33852(8) 0.0217(2) Uani d . 1 . .
N N1 -0.1894(2) 0.78466(13) 0.22558(10) 0.0180(3) Uani d . 1 . .
N N2 -0.1881(2) 0.93860(13) 0.08657(10) 0.0196(3) Uani d . 1 . .
N N3 -0.0355(2) 0.84999(13) 0.07092(10) 0.0190(3) Uani d . 1 . .
H H3N 0.052(3) 0.866(2) 0.0191(17) 0.033(5) Uiso d . 1 . .
N N4 0.1037(2) 0.66518(13) 0.17503(10) 0.0179(3) Uani d . 1 . .
H H4N 0.111(3) 0.643(2) 0.2411(17) 0.028(5) Uiso d . 1 . .
N N5 0.3803(2) 0.52952(13) 0.15529(10) 0.0187(3) Uani d . 1 . .
H H5N 0.458(3) 0.494(2) 0.1140(15) 0.020(4) Uiso d . 1 . .
C C1 -0.5206(3) 0.91936(16) 0.33573(12) 0.0208(3) Uani d . 1 . .
H H1 -0.4508 0.8519 0.3742 0.025 Uiso calc R 1 . .
C C2 -0.6883(3) 0.97955(17) 0.38396(13) 0.0246(3) Uani d . 1 . .
H H2 -0.7334 0.9528 0.4553 0.030 Uiso calc R 1 . .
C C3 -0.7902(3) 1.07873(17) 0.32819(14) 0.0254(3) Uani d . 1 . .
H H3 -0.9047 1.1199 0.3614 0.030 Uiso calc R 1 . .
C C4 -0.7245(3) 1.11747(16) 0.22403(13) 0.0237(3) Uani d . 1 . .
H H4 -0.7936 1.1857 0.1861 0.028 Uiso calc R 1 . .
C C5 -0.5586(3) 1.05716(16) 0.17507(12) 0.0204(3) Uani d . 1 . .
H H5 -0.5154 1.0833 0.1034 0.024 Uiso calc R 1 . .
C C6 -0.4547(2) 0.95789(15) 0.23090(12) 0.0175(3) Uani d . 1 . .
C C7 -0.2773(2) 0.89424(15) 0.17999(12) 0.0172(3) Uani d . 1 . .
C C8 -0.0381(2) 0.76241(15) 0.15491(11) 0.0173(3) Uani d . 1 . .
C C9 0.2436(2) 0.61501(15) 0.10695(11) 0.0170(3) Uani d . 1 . .
C C10 0.4197(2) 0.51397(15) 0.26620(12) 0.0181(3) Uani d . 1 . .
C C11 0.6496(3) 0.42025(17) 0.39532(12) 0.0246(3) Uani d . 1 . .
H H11A 0.5123 0.3763 0.4334 0.030 Uiso calc R 1 . .
H H11B 0.7187 0.5134 0.4339 0.030 Uiso calc R 1 . .
C C12 0.8169(3) 0.32036(17) 0.39450(14) 0.0250(3) Uani d . 1 . .
H H12A 0.7455 0.2281 0.3572 0.037 Uiso calc R 1 . .
H H12B 0.8636 0.3033 0.4702 0.037 Uiso calc R 1 . .
H H12C 0.9508 0.3645 0.3556 0.037 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
C10 O1 C11 . . 115.00(11) ?
C8 N1 C7 . . 102.43(12) ?
C7 N2 N3 . . 102.54(11) ?
C8 N3 N2 . . 109.22(12) ?
C8 N3 H3N . . 131.7(14) ?
N2 N3 H3N . . 118.4(14) ?
C9 N4 C8 . . 128.91(13) ?
C9 N4 H4N . . 117.6(13) ?
C8 N4 H4N . . 113.1(13) ?
C10 N5 C9 . . 127.10(13) ?
C10 N5 H5N . . 116.8(13) ?
C9 N5 H5N . . 115.5(13) ?
C2 C1 C6 . . 120.04(14) ?
C2 C1 H1 . . 120.0 ?
C6 C1 H1 . . 120.0 ?
C1 C2 C3 . . 120.18(14) ?
C1 C2 H2 . . 119.9 ?
C3 C2 H2 . . 119.9 ?
C4 C3 C2 . . 119.88(14) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C5 C4 C3 . . 120.28(14) ?
C5 C4 H4 . . 119.9 ?
C3 C4 H4 . . 119.9 ?
C4 C5 C6 . . 120.13(14) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C1 C6 C5 . . 119.48(13) ?
C1 C6 C7 . . 120.00(13) ?
C5 C6 C7 . . 120.52(13) ?
N2 C7 N1 . . 114.46(13) ?
N2 C7 C6 . . 122.90(13) ?
N1 C7 C6 . . 122.64(13) ?
N1 C8 N3 . . 111.32(12) ?
N1 C8 N4 . . 121.13(13) ?
N3 C8 N4 . . 127.42(13) ?
N4 C9 N5 . . 114.77(12) ?
N4 C9 S1 . . 125.65(11) ?
N5 C9 S1 . . 119.58(11) ?
O2 C10 O1 . . 125.48(13) ?
O2 C10 N5 . . 125.13(13) ?
O1 C10 N5 . . 109.38(12) ?
O1 C11 C12 . . 106.95(12) ?
O1 C11 H11A . . 110.3 ?
C12 C11 H11A . . 110.3 ?
O1 C11 H11B . . 110.3 ?
C12 C11 H11B . . 110.3 ?
H11A C11 H11B . . 108.6 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 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 C9 . 1.6632(14) ?
O1 C10 . 1.3274(17) ?
O1 C11 . 1.4568(17) ?
O2 C10 . 1.2142(18) ?
N1 C8 . 1.3194(18) ?
N1 C7 . 1.3680(18) ?
N2 C7 . 1.3260(19) ?
N2 N3 . 1.3674(17) ?
N3 C8 . 1.3345(18) ?
N3 H3N . 0.84(2) ?
N4 C9 . 1.3440(18) ?
N4 C8 . 1.3845(18) ?
N4 H4N . 0.84(2) ?
N5 C10 . 1.3803(18) ?
N5 C9 . 1.3811(18) ?
N5 H5N . 0.81(2) ?
C1 C2 . 1.389(2) ?
C1 C6 . 1.394(2) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.390(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.386(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.385(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.397(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.4685(19) ?
C11 C12 . 1.501(2) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 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
N5 H5N S1 2_665 0.81(2) 2.58(2) 3.3739(13) 166.0(17)
N4 H4N O2 . 0.84(2) 1.97(2) 2.6448(16) 137.3(18)
N3 H3N S1 . 0.84(2) 2.67(2) 3.0926(13) 113.0(16)
N3 H3N N2 2_575 0.84(2) 2.32(2) 2.9838(18) 136.5(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744344
