#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/42/2014200.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_2014200
loop_
_publ_author_name
'Fangfang Jian'
'Hailian Xiao'
'Yongqi Qin'
'Liangzhong Xu'
_publ_section_title
;
 2-Benzoyl-N-phenyl-2-(1,2,4-triazol-1-yl)thioacetamide and
 2-(4-methoxybenzoyl)-N-phenyl-2-(1,2,4-triazol-1-yl)thioacetamide
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o492
_journal_page_last               o493
_journal_paper_doi               10.1107/S0108270104012351
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C17 H14 N4 O S'
_chemical_formula_moiety         'C17 H14 N4 O S'
_chemical_formula_sum            'C17 H14 N4 O S'
_chemical_formula_weight         322.38
_chemical_name_systematic
;
2-Benzoyl-N-phenyl-2-(1,2,4-triazol-1-yl)thioacetamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 105.88(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8060(18)
_cell_length_b                   12.097(2)
_cell_length_c                   14.809(3)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      2
_cell_volume                     1517.3(6)
_computing_cell_refinement       'R-AXIS Software'
_computing_data_collection       'R-AXIS Software (Rigaku, 1997)'
_computing_data_reduction        'R-AXIS Software'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990b)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990a)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.874
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Oxford Instruments point detector'
_diffrn_measurement_method       θ/2θ
_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  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5518
_diffrn_reflns_theta_full        26.51
_diffrn_reflns_theta_max         26.51
_diffrn_reflns_theta_min         2.21
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       pillar
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.190
_refine_ls_extinction_coef       0.0133(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0404
_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)+(0.0488P)²+0.2377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1030
_reflns_number_gt                2314
_reflns_number_total             3055
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na1659.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_Hall     '-P 2y bc'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2014200
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_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
_atom_site_type_symbol
S1 0.60565(6) 0.22561(4) 0.25140(4) 0.04635(18) Uani d . 1 . . S
O1 0.95863(16) 0.20732(12) 0.46472(10) 0.0479(4) Uani d . 1 . . O
N1 0.66517(16) 0.01437(12) 0.20930(10) 0.0322(3) Uani d . 1 . . N
H1A 0.7376 -0.0353 0.2199 0.039 Uiso calc R 1 . . H
N2 1.04861(19) 0.14709(14) 0.22077(12) 0.0411(4) Uani d . 1 . . N
N3 1.10034(18) 0.32874(14) 0.25183(12) 0.0411(4) Uani d . 1 . . N
N4 0.97639(16) 0.18423(12) 0.28582(11) 0.0324(3) Uani d . 1 . . N
C1 0.3754(2) 0.02803(18) 0.14525(15) 0.0438(5) Uani d . 1 . . C
H1B 0.3694 0.0816 0.1891 0.053 Uiso calc R 1 . . H
C2 0.2401(2) -0.00698(19) 0.07853(17) 0.0524(6) Uani d . 1 . . C
H2B 0.1433 0.0244 0.0775 0.063 Uiso calc R 1 . . H
C3 0.2468(2) -0.08728(19) 0.01398(15) 0.0487(5) Uani d . 1 . . C
H3B 0.1558 -0.1087 -0.0313 0.058 Uiso calc R 1 . . H
C4 0.3897(2) -0.13574(17) 0.01711(14) 0.0437(5) Uani d . 1 . . C
H4A 0.3945 -0.1917 -0.0250 0.052 Uiso calc R 1 . . H
C5 0.5255(2) -0.10163(15) 0.08247(13) 0.0368(4) Uani d . 1 . . C
H5A 0.6215 -0.1347 0.0844 0.044 Uiso calc R 1 . . H
C6 0.5190(2) -0.01775(15) 0.14557(12) 0.0313(4) Uani d . 1 . . C
C7 0.70743(19) 0.10999(14) 0.25532(12) 0.0302(4) Uani d . 1 . . C
C8 0.87825(19) 0.10642(14) 0.31995(12) 0.0306(4) Uani d . 1 . . C
H8A 0.9198 0.0319 0.3165 0.037 Uiso calc R 1 . . H
C9 1.1203(2) 0.23689(17) 0.20362(15) 0.0442(5) Uani d . 1 . . C
H9A 1.1810 0.2375 0.1611 0.053 Uiso calc R 1 . . H
C10 1.0075(2) 0.29222(16) 0.30207(15) 0.0414(5) Uani d . 1 . . C
H10A 0.9692 0.3353 0.3429 0.050 Uiso calc R 1 . . H
C11 0.8834(2) 0.12955(15) 0.42344(13) 0.0344(4) Uani d . 1 . . C
C12 0.7988(2) 0.05222(16) 0.47172(13) 0.0349(4) Uani d . 1 . . C
C13 0.7414(2) -0.05099(17) 0.43599(15) 0.0427(5) Uani d . 1 . . C
H13A 0.7513 -0.0732 0.3778 0.051 Uiso calc R 1 . . H
C14 0.6701(2) -0.12046(19) 0.48630(16) 0.0495(5) Uani d . 1 . . C
H14A 0.6338 -0.1896 0.4624 0.059 Uiso calc R 1 . . H
C15 0.6528(2) -0.0873(2) 0.57203(16) 0.0512(6) Uani d . 1 . . C
H15A 0.6034 -0.1337 0.6055 0.061 Uiso calc R 1 . . H
C16 0.7088(3) 0.0151(2) 0.60830(15) 0.0519(6) Uani d . 1 . . C
H16A 0.6971 0.0372 0.6661 0.062 Uiso calc R 1 . . H
C17 0.7819(2) 0.08434(18) 0.55880(14) 0.0432(5) Uani d . 1 . . C
H17A 0.8200 0.1528 0.5837 0.052 Uiso calc R 1 . . H
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
C7 N1 C6 130.11(15)
C7 N1 H1A 114.9
C6 N1 H1A 114.9
C9 N2 N4 101.78(16)
C10 N3 C9 102.29(16)
C10 N4 N2 109.62(15)
C10 N4 C8 132.54(15)
N2 N4 C8 117.75(14)
C6 C1 C2 119.12(19)
C6 C1 H1B 120.4
C2 C1 H1B 120.4
C3 C2 C1 121.11(19)
C3 C2 H2B 119.4
C1 C2 H2B 119.4
C2 C3 C4 119.42(19)
C2 C3 H3B 120.3
C4 C3 H3B 120.3
C3 C4 C5 120.29(19)
C3 C4 H4A 119.9
C5 C4 H4A 119.9
C4 C5 C6 120.09(18)
C4 C5 H5A 120.0
C6 C5 H5A 120.0
C1 C6 C5 119.87(17)
C1 C6 N1 123.58(17)
C5 C6 N1 116.53(15)
N1 C7 C8 112.09(15)
N1 C7 S1 129.72(13)
C8 C7 S1 118.19(13)
N4 C8 C11 111.55(14)
N4 C8 C7 109.57(14)
C11 C8 C7 111.56(13)
N4 C8 H8A 108.0
C11 C8 H8A 108.0
C7 C8 H8A 108.0
N2 C9 N3 115.83(18)
N2 C9 H9A 122.1
N3 C9 H9A 122.1
N3 C10 N4 110.47(17)
N3 C10 H10A 124.8
N4 C10 H10A 124.8
O1 C11 C12 121.18(17)
O1 C11 C8 120.25(17)
C12 C11 C8 118.54(15)
C17 C12 C13 118.81(18)
C17 C12 C11 117.51(17)
C13 C12 C11 123.64(17)
C14 C13 C12 120.6(2)
C14 C13 H13A 119.7
C12 C13 H13A 119.7
C15 C14 C13 120.0(2)
C15 C14 H14A 120.0
C13 C14 H14A 120.0
C14 C15 C16 120.0(2)
C14 C15 H15A 120.0
C16 C15 H15A 120.0
C17 C16 C15 120.2(2)
C17 C16 H16A 119.9
C15 C16 H16A 119.9
C16 C17 C12 120.3(2)
C16 C17 H17A 119.8
C12 C17 H17A 119.8
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 C7 . 1.6536(18) yes
O1 C11 . 1.214(2) yes
N1 C7 . 1.342(2) yes
N1 C6 . 1.425(2) yes
N1 H1A . 0.8600 ?
N2 C9 . 1.314(2) yes
N2 N4 . 1.368(2) yes
N3 C10 . 1.322(2) ?
N3 C9 . 1.359(3) ?
N4 C10 . 1.343(2) ?
N4 C8 . 1.457(2) ?
C1 C6 . 1.380(3) ?
C1 C2 . 1.389(3) ?
C1 H1B . 0.9300 ?
C2 C3 . 1.376(3) ?
C2 H2B . 0.9300 ?
C3 C4 . 1.378(3) ?
C3 H3B . 0.9300 ?
C4 C5 . 1.379(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.392(3) ?
C5 H5A . 0.9300 ?
C7 C8 . 1.547(2) ?
C8 C11 . 1.547(3) ?
C8 H8A . 0.9800 ?
C9 H9A . 0.9300 ?
C10 H10A . 0.9300 ?
C11 C12 . 1.492(3) ?
C12 C17 . 1.394(3) ?
C12 C13 . 1.395(3) ?
C13 C14 . 1.381(3) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.380(3) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.385(3) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.381(3) ?
C16 H16A . 0.9300 ?
C17 H17A . 0.9300 ?
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
_geom_hbond_publ_flag
N1 H1A N3 2_745 0.86 2.14 2.998(2) 174 yes
C1 H1B S1 ? 0.93 2.67 3.248(2) 120 yes
C10 H10A O1 ? 0.93 2.40 2.758(3) 103 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9884289
