#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/93/2229313.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_2229313
loop_
_publ_author_name
'Wang, Wei'
'Gao, Yan'
'Xiao, Zuo-bing'
'Yao, Hong-guo'
'Zhang, Jing-jing'
_publ_section_title
;
 rac-4-Amino-1-(2-benzoyl-1-phenylethyl)-3-methyl-1H-1,2,4-triazole-5(4H)-thione
;
_journal_coeditor_code           ZS2086
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o348
_journal_paper_doi               10.1107/S1600536810054255
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H18 N4 O S'
_chemical_formula_moiety         'C18 H18 N4 O S'
_chemical_formula_sum            'C18 H18 N4 O S'
_chemical_formula_weight         338.42
_chemical_name_systematic
;
rac-4-Amino-1-(2-benzoyl-1-phenylethyl)-3-methyl-1H-
1,2,4-triazole-5(4H)-thione
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.604(4)
_cell_length_b                   10.199(2)
_cell_length_c                   19.241(4)
_cell_measurement_reflns_used    7030
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.874
_cell_measurement_theta_min      2.117
_cell_volume                     3454.6(13)
_computing_cell_refinement       'Crystalclear (Rigaku/MSC, 2005)'
_computing_data_collection       'Crystalclear (Rigaku/MSC, 2005)'
_computing_data_reduction        'Crystalclear (Rigaku/MSC, 2005)'
_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      293(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25430
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.12
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.9537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.292
_refine_ls_extinction_coef       0.0148(12)
_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   1.131
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3040
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0551
_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)+(0.0600P)²+1.1394P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1372
_reflns_number_gt                2527
_reflns_number_total             3040
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2086.cif
_cod_data_source_block           I
_cod_original_cell_volume        3454.5(13)
_cod_database_code               2229313
_cod_database_fobs_code          2229313
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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 0.20040(3) 0.45904(6) 0.42466(4) 0.0526(2) Uani d . 1 . .
O O1 0.38811(10) 0.67534(18) 0.34992(8) 0.0550(5) Uani d . 1 . .
N N1 0.28460(14) 0.2386(2) 0.33526(11) 0.0550(6) Uani d D 1 . .
H H1A 0.2383(9) 0.276(2) 0.3333(17) 0.101(13) Uiso d D 1 . .
H H1B 0.2847(14) 0.1601(16) 0.3563(14) 0.074(10) Uiso d D 1 . .
N N2 0.32401(11) 0.31994(19) 0.38230(9) 0.0437(5) Uani d . 1 . .
N N3 0.35336(10) 0.47896(19) 0.44806(10) 0.0427(5) Uani d . 1 . .
N N4 0.42070(11) 0.4176(2) 0.43219(10) 0.0494(5) Uani d . 1 . .
C C1 0.49061(13) 0.8173(2) 0.37434(12) 0.0472(6) Uani d . 1 . .
C C2 0.49301(16) 0.8628(3) 0.30604(13) 0.0598(7) Uani d . 1 . .
H H2 0.4568 0.8345 0.2742 0.072 Uiso calc R 1 . .
C C3 0.54873(19) 0.9494(3) 0.28535(17) 0.0732(9) Uani d . 1 . .
H H3 0.5496 0.9796 0.2398 0.088 Uiso calc R 1 . .
C C4 0.60258(19) 0.9911(3) 0.33125(19) 0.0778(9) Uani d . 1 . .
H H4 0.6403 1.0486 0.3167 0.093 Uiso calc R 1 . .
C C5 0.60126(18) 0.9482(3) 0.39905(19) 0.0754(9) Uani d . 1 . .
H H5 0.6379 0.9771 0.4303 0.091 Uiso calc R 1 . .
C C6 0.54545(15) 0.8625(3) 0.42060(14) 0.0606(7) Uani d . 1 . .
H H6 0.5445 0.8345 0.4666 0.073 Uiso calc R 1 . .
C C7 0.43012(13) 0.7222(2) 0.39396(12) 0.0439(6) Uani d . 1 . .
C C8 0.42195(13) 0.6852(2) 0.46984(11) 0.0438(6) Uani d . 1 . .
H H8A 0.4203 0.7649 0.4974 0.053 Uiso calc R 1 . .
H H8B 0.4666 0.6363 0.4839 0.053 Uiso calc R 1 . .
C C9 0.35175(12) 0.6038(2) 0.48612(11) 0.0421(6) Uani d . 1 . .
H H9 0.3075 0.6531 0.4696 0.051 Uiso calc R 1 . .
C C10 0.34152(13) 0.5820(3) 0.56370(12) 0.0451(6) Uani d . 1 . .
C C11 0.30483(17) 0.6765(3) 0.60210(14) 0.0659(8) Uani d . 1 . .
H H11 0.2866 0.7518 0.5804 0.079 Uiso calc R 1 . .
C C12 0.2949(2) 0.6597(4) 0.67341(15) 0.0805(10) Uani d . 1 . .
H H12 0.2703 0.7239 0.6994 0.097 Uiso calc R 1 . .
C C13 0.32127(19) 0.5483(4) 0.70528(15) 0.0757(9) Uani d . 1 . .
H H13 0.3153 0.5376 0.7530 0.091 Uiso calc R 1 . .
C C14 0.3560(2) 0.4543(4) 0.66734(16) 0.0847(11) Uani d . 1 . .
H H14 0.3729 0.3781 0.6890 0.102 Uiso calc R 1 . .
C C15 0.36657(19) 0.4705(3) 0.59659(15) 0.0734(9) Uani d . 1 . .
H H15 0.3908 0.4053 0.5711 0.088 Uiso calc R 1 . .
C C16 0.29294(13) 0.4212(2) 0.41909(11) 0.0399(5) Uani d . 1 . .
C C17 0.40078(14) 0.3207(2) 0.39139(12) 0.0463(6) Uani d . 1 . .
C C18 0.45268(16) 0.2216(3) 0.36137(14) 0.0629(7) Uani d . 1 . .
H H18A 0.5043 0.2491 0.3679 0.094 Uiso calc R 1 . .
H H18B 0.4425 0.2124 0.3126 0.094 Uiso calc R 1 . .
H H18C 0.4448 0.1389 0.3841 0.094 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
?
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
N2 N1 H1A . . 103(2) ?
N2 N1 H1B . . 103.5(19) ?
H1A N1 H1B . . 113.5(16) ?
C17 N2 C16 . . 109.03(19) ?
C17 N2 N1 . . 125.0(2) ?
C16 N2 N1 . . 125.5(2) ?
C16 N3 N4 . . 113.11(19) ?
C16 N3 C9 . . 125.05(18) ?
N4 N3 C9 . . 121.46(18) ?
C17 N4 N3 . . 104.22(19) ?
C6 C1 C2 . . 118.2(2) ?
C6 C1 C7 . . 123.3(2) ?
C2 C1 C7 . . 118.5(2) ?
C3 C2 C1 . . 120.4(3) ?
C3 C2 H2 . . 119.8 ?
C1 C2 H2 . . 119.8 ?
C4 C3 C2 . . 120.5(3) ?
C4 C3 H3 . . 119.8 ?
C2 C3 H3 . . 119.8 ?
C3 C4 C5 . . 120.2(3) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C4 C5 C6 . . 119.9(3) ?
C4 C5 H5 . . 120.1 ?
C6 C5 H5 . . 120.1 ?
C5 C6 C1 . . 120.8(3) ?
C5 C6 H6 . . 119.6 ?
C1 C6 H6 . . 119.6 ?
O1 C7 C1 . . 120.8(2) ?
O1 C7 C8 . . 120.9(2) ?
C1 C7 C8 . . 118.3(2) ?
C7 C8 C9 . . 114.30(19) ?
C7 C8 H8A . . 108.7 ?
C9 C8 H8A . . 108.7 ?
C7 C8 H8B . . 108.7 ?
C9 C8 H8B . . 108.7 ?
H8A C8 H8B . . 107.6 ?
N3 C9 C10 . . 111.4(2) ?
N3 C9 C8 . . 110.77(17) ?
C10 C9 C8 . . 112.23(18) ?
N3 C9 H9 . . 107.4 ?
C10 C9 H9 . . 107.4 ?
C8 C9 H9 . . 107.4 ?
C15 C10 C11 . . 118.9(2) ?
C15 C10 C9 . . 122.3(2) ?
C11 C10 C9 . . 118.7(2) ?
C10 C11 C12 . . 120.1(3) ?
C10 C11 H11 . . 119.9 ?
C12 C11 H11 . . 119.9 ?
C13 C12 C11 . . 119.9(3) ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C14 C13 C12 . . 120.0(3) ?
C14 C13 H13 . . 120.0 ?
C12 C13 H13 . . 120.0 ?
C13 C14 C15 . . 120.5(3) ?
C13 C14 H14 . . 119.7 ?
C15 C14 H14 . . 119.7 ?
C10 C15 C14 . . 120.5(3) ?
C10 C15 H15 . . 119.7 ?
C14 C15 H15 . . 119.7 ?
N3 C16 N2 . . 103.33(19) ?
N3 C16 S1 . . 130.09(18) ?
N2 C16 S1 . . 126.58(18) ?
N4 C17 N2 . . 110.3(2) ?
N4 C17 C18 . . 125.7(2) ?
N2 C17 C18 . . 123.9(2) ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 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 C16 . 1.678(2) ?
O1 C7 . 1.222(3) ?
N1 N2 . 1.410(3) ?
N1 H1A . 0.900(10) ?
N1 H1B . 0.897(10) ?
N2 C17 . 1.363(3) ?
N2 C16 . 1.366(3) ?
N3 C16 . 1.338(3) ?
N3 N4 . 1.375(3) ?
N3 C9 . 1.469(3) ?
N4 C17 . 1.310(3) ?
C1 C6 . 1.392(3) ?
C1 C2 . 1.394(3) ?
C1 C7 . 1.489(3) ?
C2 C3 . 1.379(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.363(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.376(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.379(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.515(3) ?
C8 C9 . 1.521(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.520(3) ?
C9 H9 . 0.9800 ?
C10 C15 . 1.375(4) ?
C10 C11 . 1.375(4) ?
C11 C12 . 1.394(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.372(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.351(5) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.384(4) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C17 C18 . 1.480(3) ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
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 O1 8_655 0.901(17) 2.472(17) 3.121(3) 129.3(17) yes
N1 H1A S1 . 0.901(17) 2.65(3) 3.195(2) 120(2) yes
N1 H1B S1 8_655 0.897(19) 2.450(10) 3.340(3) 171.6(19) 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
C16 N3 N4 C17 . . . . 1.0(3) ?
C9 N3 N4 C17 . . . . -172.2(2) ?
C6 C1 C2 C3 . . . . 0.4(4) ?
C7 C1 C2 C3 . . . . -179.0(2) ?
C1 C2 C3 C4 . . . . 0.5(4) ?
C2 C3 C4 C5 . . . . -0.8(5) ?
C3 C4 C5 C6 . . . . 0.3(5) ?
C4 C5 C6 C1 . . . . 0.7(5) ?
C2 C1 C6 C5 . . . . -1.0(4) ?
C7 C1 C6 C5 . . . . 178.5(3) ?
C6 C1 C7 O1 . . . . -172.5(2) ?
C2 C1 C7 O1 . . . . 7.0(3) ?
C6 C1 C7 C8 . . . . 7.6(3) ?
C2 C1 C7 C8 . . . . -173.0(2) ?
O1 C7 C8 C9 . . . . -8.5(3) ?
C1 C7 C8 C9 . . . . 171.4(2) ?
C16 N3 C9 C10 . . . . 93.1(3) ?
N4 N3 C9 C10 . . . . -94.6(2) ?
C16 N3 C9 C8 . . . . -141.2(2) ?
N4 N3 C9 C8 . . . . 31.1(3) ?
C7 C8 C9 N3 . . . . 61.1(2) ?
C7 C8 C9 C10 . . . . -173.70(19) ?
N3 C9 C10 C15 . . . . 28.7(3) ?
C8 C9 C10 C15 . . . . -96.1(3) ?
N3 C9 C10 C11 . . . . -150.2(2) ?
C8 C9 C10 C11 . . . . 84.9(3) ?
C15 C10 C11 C12 . . . . 1.3(4) ?
C9 C10 C11 C12 . . . . -179.7(3) ?
C10 C11 C12 C13 . . . . -0.4(5) ?
C11 C12 C13 C14 . . . . -0.9(5) ?
C12 C13 C14 C15 . . . . 1.3(6) ?
C11 C10 C15 C14 . . . . -0.9(5) ?
C9 C10 C15 C14 . . . . -179.9(3) ?
C13 C14 C15 C10 . . . . -0.4(6) ?
N4 N3 C16 N2 . . . . -1.0(2) ?
C9 N3 C16 N2 . . . . 171.9(2) ?
N4 N3 C16 S1 . . . . 178.93(17) ?
C9 N3 C16 S1 . . . . -8.1(4) ?
C17 N2 C16 N3 . . . . 0.7(2) ?
N1 N2 C16 N3 . . . . -171.6(2) ?
C17 N2 C16 S1 . . . . -179.32(18) ?
N1 N2 C16 S1 . . . . 8.4(3) ?
N3 N4 C17 N2 . . . . -0.6(3) ?
N3 N4 C17 C18 . . . . -178.0(2) ?
C16 N2 C17 N4 . . . . -0.1(3) ?
N1 N2 C17 N4 . . . . 172.2(2) ?
C16 N2 C17 C18 . . . . 177.4(2) ?
N1 N2 C17 C18 . . . . -10.3(4) ?
