#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/90/2229005.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_2229005
loop_
_publ_author_name
'Song, Xiao-qiu'
'Ye, Lin'
'Wang, He-wen'
_publ_section_title
;
 4-Amino-1-(2-benzoyl-1-phenylethyl)-3-phenyl-1H-1,2,4-triazol-5(4H)-thione
;
_journal_coeditor_code           CV5022
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o347
_journal_paper_doi               10.1107/S1600536810054553
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C23 H20 N4 O S'
_chemical_formula_moiety         'C23 H20 N4 O S'
_chemical_formula_sum            'C23 H20 N4 O S'
_chemical_formula_weight         400.49
_chemical_name_systematic
;
4-Amino-1-(2-benzoyl-1-phenylethyl)-3-phenyl-1H-1,2,4-triazol-
5(4H)-thione
;
_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
_cell_angle_alpha                111.80(3)
_cell_angle_beta                 111.01(3)
_cell_angle_gamma                98.91(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4625(19)
_cell_length_b                   11.340(2)
_cell_length_c                   11.655(2)
_cell_measurement_reflns_used    3363
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.835
_cell_measurement_theta_min      2.051
_cell_volume                     1022.4(6)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0515
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9308
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.9822
_exptl_absorpt_correction_T_min  0.9649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.287
_refine_ls_extinction_coef       0.107(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3590
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0710P)²+0.1941P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1207
_reflns_number_gt                2686
_reflns_number_total             3590
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv5022.cif
_cod_data_source_block           I
_cod_original_cell_volume        1022.4(4)
_cod_database_code               2229005
_cod_database_fobs_code          2229005
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 0.54562(6) -0.11721(5) 0.13685(5) 0.02158(19) Uani d . 1 . .
O O1 0.45937(17) 0.25822(14) 0.24735(14) 0.0237(4) Uani d . 1 . .
N N1 0.82240(19) 0.25821(16) 0.32190(16) 0.0182(4) Uani d . 1 . .
N N2 0.72008(19) 0.15086(16) 0.31246(16) 0.0163(4) Uani d . 1 . .
N N3 0.75632(19) 0.07328(15) 0.13230(15) 0.0159(4) Uani d . 1 . .
N N4 0.7447(2) -0.01242(17) 0.00269(17) 0.0213(4) Uani d D 1 . .
H H4A 0.703(2) -0.0962(13) -0.010(2) 0.036(7) Uiso d D 1 . .
H H4B 0.675(2) 0.005(2) -0.062(2) 0.055(9) Uiso d D 1 . .
C C1 0.9302(2) 0.4216(2) 0.2059(2) 0.0231(5) Uani d . 1 . .
H H1 0.8614 0.4514 0.2443 0.028 Uiso calc R 1 . .
C C2 1.0231(3) 0.5072(2) 0.1812(2) 0.0252(5) Uani d . 1 . .
H H2 1.0168 0.5949 0.2010 0.030 Uiso calc R 1 . .
C C3 1.1260(2) 0.4637(2) 0.1269(2) 0.0257(5) Uani d . 1 . .
H H3 1.1913 0.5223 0.1111 0.031 Uiso calc R 1 . .
C C4 1.1330(3) 0.3347(2) 0.0962(2) 0.0260(5) Uani d . 1 . .
H H4 1.2038 0.3059 0.0600 0.031 Uiso calc R 1 . .
C C5 1.0376(2) 0.2475(2) 0.1179(2) 0.0221(5) Uani d . 1 . .
H H5 1.0408 0.1586 0.0943 0.026 Uiso calc R 1 . .
C C6 0.9371(2) 0.2915(2) 0.17470(19) 0.0176(4) Uani d . 1 . .
C C7 0.8422(2) 0.20849(19) 0.21041(19) 0.0176(5) Uani d . 1 . .
C C8 0.6737(2) 0.03559(19) 0.19571(19) 0.0160(4) Uani d . 1 . .
C C9 0.6600(2) 0.17172(19) 0.41591(19) 0.0178(5) Uani d . 1 . .
H H9 0.5473 0.1088 0.3687 0.021 Uiso calc R 1 . .
C C10 0.7610(2) 0.14453(18) 0.53269(19) 0.0176(4) Uani d . 1 . .
C C11 0.9151(2) 0.1418(2) 0.5597(2) 0.0222(5) Uani d . 1 . .
H H11 0.9606 0.1555 0.5032 0.027 Uiso calc R 1 . .
C C12 1.0040(3) 0.1191(2) 0.6688(2) 0.0245(5) Uani d . 1 . .
H H12 1.1093 0.1169 0.6861 0.029 Uiso calc R 1 . .
C C13 0.9392(3) 0.0995(2) 0.7523(2) 0.0237(5) Uani d . 1 . .
H H13 0.9991 0.0824 0.8259 0.028 Uiso calc R 1 . .
C C14 0.7863(3) 0.1051(2) 0.7281(2) 0.0250(5) Uani d . 1 . .
H H14 0.7426 0.0939 0.7866 0.030 Uiso calc R 1 . .
C C15 0.6970(2) 0.1268(2) 0.6188(2) 0.0215(5) Uani d . 1 . .
H H15 0.5921 0.1297 0.6023 0.026 Uiso calc R 1 . .
C C16 0.6580(2) 0.31677(19) 0.47288(19) 0.0187(5) Uani d . 1 . .
H H16A 0.6083 0.3303 0.5364 0.022 Uiso calc R 1 . .
H H16B 0.7697 0.3799 0.5269 0.022 Uiso calc R 1 . .
C C17 0.5659(2) 0.3486(2) 0.35832(19) 0.0174(4) Uani d . 1 . .
C C18 0.6095(2) 0.4905(2) 0.3827(2) 0.0188(5) Uani d . 1 . .
C C19 0.6976(2) 0.5982(2) 0.5161(2) 0.0229(5) Uani d . 1 . .
H H19 0.7328 0.5816 0.5941 0.028 Uiso calc R 1 . .
C C20 0.7336(3) 0.7291(2) 0.5348(2) 0.0278(5) Uani d . 1 . .
H H20 0.7929 0.8020 0.6258 0.033 Uiso calc R 1 . .
C C21 0.6842(3) 0.7544(2) 0.4223(3) 0.0298(6) Uani d . 1 . .
H H21 0.7084 0.8445 0.4361 0.036 Uiso calc R 1 . .
C C22 0.5990(3) 0.6483(2) 0.2889(2) 0.0317(6) Uani d . 1 . .
H H22 0.5672 0.6657 0.2114 0.038 Uiso calc R 1 . .
C C23 0.5603(3) 0.5168(2) 0.2688(2) 0.0261(5) Uani d . 1 . .
H H23 0.5003 0.4443 0.1775 0.031 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 0.0106
; International Tables
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
S S 0.1246 0.1246
; International Tables
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
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
C7 N1 N2 . . 104.69(16) ?
C8 N2 N1 . . 113.11(16) ?
C8 N2 C9 . . 126.58(17) ?
N1 N2 C9 . . 120.00(15) ?
C8 N3 C7 . . 109.01(16) ?
C8 N3 N4 . . 124.81(16) ?
C7 N3 N4 . . 126.05(17) ?
N3 N4 H4A . . 104.0(15) ?
N3 N4 H4B . . 106.7(17) ?
H4A N4 H4B . . 111.0(14) ?
C2 C1 C6 . . 120.4(2) ?
C2 C1 H1 . . 119.8 ?
C6 C1 H1 . . 119.8 ?
C1 C2 C3 . . 119.5(2) ?
C1 C2 H2 . . 120.2 ?
C3 C2 H2 . . 120.2 ?
C4 C3 C2 . . 120.0(2) ?
C4 C3 H3 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
C3 C4 C5 . . 120.7(2) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
C4 C5 C6 . . 119.5(2) ?
C4 C5 H5 . . 120.3 ?
C6 C5 H5 . . 120.3 ?
C5 C6 C1 . . 119.83(19) ?
C5 C6 C7 . . 122.41(19) ?
C1 C6 C7 . . 117.70(18) ?
N1 C7 N3 . . 110.27(18) ?
N1 C7 C6 . . 122.88(17) ?
N3 C7 C6 . . 126.76(17) ?
N2 C8 N3 . . 102.87(16) ?
N2 C8 S1 . . 130.11(16) ?
N3 C8 S1 . . 127.01(14) ?
N2 C9 C10 . . 112.15(16) ?
N2 C9 C16 . . 107.96(16) ?
C10 C9 C16 . . 111.00(16) ?
N2 C9 H9 . . 108.6 ?
C10 C9 H9 . . 108.6 ?
C16 C9 H9 . . 108.6 ?
C11 C10 C15 . . 118.93(18) ?
C11 C10 C9 . . 122.58(18) ?
C15 C10 C9 . . 118.44(18) ?
C10 C11 C12 . . 120.6(2) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C13 C12 C11 . . 120.2(2) ?
C13 C12 H12 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
C12 C13 C14 . . 119.66(19) ?
C12 C13 H13 . . 120.2 ?
C14 C13 H13 . . 120.2 ?
C15 C14 C13 . . 120.3(2) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C14 C15 C10 . . 120.3(2) ?
C14 C15 H15 . . 119.9 ?
C10 C15 H15 . . 119.9 ?
C17 C16 C9 . . 112.01(16) ?
C17 C16 H16A . . 109.2 ?
C9 C16 H16A . . 109.2 ?
C17 C16 H16B . . 109.2 ?
C9 C16 H16B . . 109.2 ?
H16A C16 H16B . . 107.9 ?
O1 C17 C18 . . 121.08(18) ?
O1 C17 C16 . . 120.19(18) ?
C18 C17 C16 . . 118.73(17) ?
C19 C18 C23 . . 119.19(19) ?
C19 C18 C17 . . 121.70(18) ?
C23 C18 C17 . . 119.11(18) ?
C20 C19 C18 . . 120.1(2) ?
C20 C19 H19 . . 120.0 ?
C18 C19 H19 . . 120.0 ?
C21 C20 C19 . . 120.5(2) ?
C21 C20 H20 . . 119.7 ?
C19 C20 H20 . . 119.7 ?
C20 C21 C22 . . 120.1(2) ?
C20 C21 H21 . . 120.0 ?
C22 C21 H21 . . 120.0 ?
C23 C22 C21 . . 120.0(2) ?
C23 C22 H22 . . 120.0 ?
C21 C22 H22 . . 120.0 ?
C22 C23 C18 . . 120.2(2) ?
C22 C23 H23 . . 119.9 ?
C18 C23 H23 . . 119.9 ?
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 C8 . 1.677(2) ?
O1 C17 . 1.225(2) ?
N1 C7 . 1.305(3) ?
N1 N2 . 1.375(2) ?
N2 C8 . 1.351(2) ?
N2 C9 . 1.468(3) ?
N3 C8 . 1.373(3) ?
N3 C7 . 1.374(3) ?
N3 N4 . 1.413(2) ?
N4 H4A . 0.91(2) ?
N4 H4B . 0.91(2) ?
C1 C2 . 1.387(3) ?
C1 C6 . 1.400(3) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.396(3) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.389(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.389(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.395(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.471(3) ?
C9 C10 . 1.527(3) ?
C9 C16 . 1.534(3) ?
C9 H9 . 1.0000 ?
C10 C11 . 1.386(3) ?
C10 C15 . 1.400(3) ?
C11 C12 . 1.391(3) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.385(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.387(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.387(3) ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
C16 C17 . 1.514(3) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 C18 . 1.488(3) ?
C18 C19 . 1.396(3) ?
C18 C23 . 1.400(3) ?
C19 C20 . 1.385(3) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.379(3) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.388(3) ?
C21 H21 . 0.9500 ?
C22 C23 . 1.386(3) ?
C22 H22 . 0.9500 ?
C23 H23 . 0.9500 ?
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
N4 H4A O1 2_655 0.91(2) 2.39(2) 2.873(3) 113.7(16) yes
N4 H4A S1 . 0.91(2) 2.69(2) 3.194(2) 116.3(17) no
N4 H4B S1 2_655 0.91(2) 2.662(15) 3.490(2) 151(2) yes
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
C7 N1 N2 C8 . . . . -1.1(2) ?
C7 N1 N2 C9 . . . . -175.02(17) ?
C6 C1 C2 C3 . . . . -1.1(3) ?
C1 C2 C3 C4 . . . . 1.0(3) ?
C2 C3 C4 C5 . . . . 0.4(3) ?
C3 C4 C5 C6 . . . . -1.8(3) ?
C4 C5 C6 C1 . . . . 1.6(3) ?
C4 C5 C6 C7 . . . . -175.21(18) ?
C2 C1 C6 C5 . . . . -0.2(3) ?
C2 C1 C6 C7 . . . . 176.77(18) ?
N2 N1 C7 N3 . . . . -0.5(2) ?
N2 N1 C7 C6 . . . . 176.48(17) ?
C8 N3 C7 N1 . . . . 1.8(2) ?
N4 N3 C7 N1 . . . . 177.66(16) ?
C8 N3 C7 C6 . . . . -175.02(18) ?
N4 N3 C7 C6 . . . . 0.9(3) ?
C5 C6 C7 N1 . . . . 140.4(2) ?
C1 C6 C7 N1 . . . . -36.5(3) ?
C5 C6 C7 N3 . . . . -43.1(3) ?
C1 C6 C7 N3 . . . . 139.9(2) ?
N1 N2 C8 N3 . . . . 2.1(2) ?
C9 N2 C8 N3 . . . . 175.54(16) ?
N1 N2 C8 S1 . . . . -177.12(14) ?
C9 N2 C8 S1 . . . . -3.6(3) ?
C7 N3 C8 N2 . . . . -2.2(2) ?
N4 N3 C8 N2 . . . . -178.20(15) ?
C7 N3 C8 S1 . . . . 176.97(14) ?
N4 N3 C8 S1 . . . . 1.0(3) ?
C8 N2 C9 C10 . . . . 91.8(2) ?
N1 N2 C9 C10 . . . . -95.16(19) ?
C8 N2 C9 C16 . . . . -145.64(18) ?
N1 N2 C9 C16 . . . . 27.4(2) ?
N2 C9 C10 C11 . . . . 18.4(3) ?
C16 C9 C10 C11 . . . . -102.5(2) ?
N2 C9 C10 C15 . . . . -164.09(17) ?
C16 C9 C10 C15 . . . . 75.1(2) ?
C15 C10 C11 C12 . . . . 1.3(3) ?
C9 C10 C11 C12 . . . . 178.81(18) ?
C10 C11 C12 C13 . . . . -0.3(3) ?
C11 C12 C13 C14 . . . . -1.1(3) ?
C12 C13 C14 C15 . . . . 1.5(3) ?
C13 C14 C15 C10 . . . . -0.5(3) ?
C11 C10 C15 C14 . . . . -0.9(3) ?
C9 C10 C15 C14 . . . . -178.48(17) ?
N2 C9 C16 C17 . . . . 53.6(2) ?
C10 C9 C16 C17 . . . . 176.93(16) ?
C9 C16 C17 O1 . . . . 26.2(3) ?
C9 C16 C17 C18 . . . . -152.79(18) ?
O1 C17 C18 C19 . . . . 162.63(19) ?
C16 C17 C18 C19 . . . . -18.4(3) ?
O1 C17 C18 C23 . . . . -17.1(3) ?
C16 C17 C18 C23 . . . . 161.87(18) ?
C23 C18 C19 C20 . . . . 0.8(3) ?
C17 C18 C19 C20 . . . . -178.92(18) ?
C18 C19 C20 C21 . . . . -0.5(3) ?
C19 C20 C21 C22 . . . . -0.7(3) ?
C20 C21 C22 C23 . . . . 1.5(3) ?
C21 C22 C23 C18 . . . . -1.2(3) ?
C19 C18 C23 C22 . . . . 0.0(3) ?
C17 C18 C23 C22 . . . . 179.7(2) ?
