#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/05/2230597.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_2230597
loop_
_publ_author_name
'Gao, Yan'
'Zhang, Li-hua'
'Wang, He-wen'
_publ_section_title
;
 3-(4-Amino-3-phenyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl)-3-(2-chlorophenyl)-1-phenylpropan-1-one
;
_journal_coeditor_code           CV5107
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1794
_journal_paper_doi               10.1107/S1600536811023750
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C23 H19 Cl N4 O S'
_chemical_formula_moiety         'C23 H19 Cl N4 O S'
_chemical_formula_sum            'C23 H19 Cl N4 O S'
_chemical_formula_weight         434.93
_chemical_name_systematic
;
3-(4-Amino-3-phenyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl)-
3-(2-chlorophenyl)-1-phenylpropan-1-one
;
_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                99.582(2)
_cell_angle_beta                 96.638(4)
_cell_angle_gamma                115.267(3)
_cell_formula_units_Z            2
_cell_length_a                   10.559(3)
_cell_length_b                   10.787(4)
_cell_length_c                   10.835(3)
_cell_measurement_reflns_used    3478
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.9
_cell_volume                     1076.1(6)
_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      113(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13931
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  0.9596
_exptl_absorpt_correction_T_min  0.9430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.294
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         5111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.948
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0315
_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)+(0.0349P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0788
_reflns_number_gt                3433
_reflns_number_total             5111
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv5107.cif
_cod_data_source_block           I
_cod_original_cell_volume        1076.2(6)
_cod_database_code               2230597
_cod_database_fobs_code          2230597
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.87508(4) 0.30026(4) 0.43912(3) 0.02271(9) Uani d . 1 1 . .
Cl Cl1 1.14768(4) 0.15222(4) 0.21807(4) 0.04566(13) Uani d . 1 1 . .
O O1 0.70047(10) 0.13775(10) 0.05439(9) 0.0298(2) Uani d . 1 1 . .
N N1 0.90922(11) 0.39665(11) 0.22109(10) 0.0171(2) Uani d . 1 1 . .
N N2 0.88351(11) 0.48767(11) 0.15864(10) 0.0184(2) Uani d . 1 1 . .
N N3 0.81314(11) 0.49054(11) 0.34152(9) 0.0175(2) Uani d . 1 1 . .
N N4 0.75491(14) 0.52876(15) 0.44374(11) 0.0252(3) Uani d . 1 1 . .
C C1 0.86846(13) 0.39575(13) 0.33424(11) 0.0174(3) Uani d . 1 1 . .
C C2 0.82420(13) 0.54367(13) 0.23458(11) 0.0172(3) Uani d . 1 1 . .
C C3 0.98141(13) 0.31632(13) 0.17006(12) 0.0179(3) Uani d . 1 1 . .
H H3 0.9499 0.2301 0.2049 0.021 Uiso calc R 1 1 . .
C C4 0.93753(13) 0.26682(13) 0.02470(11) 0.0183(3) Uani d . 1 1 . .
H H4C 0.9598 0.3500 -0.0121 0.022 Uiso calc R 1 1 . .
H H4D 0.9946 0.2203 -0.0067 0.022 Uiso calc R 1 1 . .
C C5 0.77970(14) 0.16486(13) -0.02188(12) 0.0201(3) Uani d . 1 1 . .
C C6 0.72490(13) 0.09573(13) -0.16117(12) 0.0191(3) Uani d . 1 1 . .
C C7 0.58247(14) -0.00620(14) -0.20344(13) 0.0263(3) Uani d . 1 1 . .
H H7 0.5211 -0.0281 -0.1443 0.032 Uiso calc R 1 1 . .
C C8 0.53048(15) -0.07543(16) -0.33125(14) 0.0344(4) Uani d . 1 1 . .
H H8 0.4331 -0.1442 -0.3600 0.041 Uiso calc R 1 1 . .
C C9 0.61981(16) -0.04485(16) -0.41761(13) 0.0332(4) Uani d . 1 1 . .
H H9 0.5838 -0.0934 -0.5053 0.040 Uiso calc R 1 1 . .
C C10 0.76108(16) 0.05597(14) -0.37670(13) 0.0266(3) Uani d . 1 1 . .
H H10 0.8221 0.0770 -0.4362 0.032 Uiso calc R 1 1 . .
C C11 0.81364(14) 0.12638(13) -0.24900(12) 0.0214(3) Uani d . 1 1 . .
H H11 0.9108 0.1960 -0.2210 0.026 Uiso calc R 1 1 . .
C C12 1.14209(13) 0.40065(14) 0.21643(11) 0.0179(3) Uani d . 1 1 . .
C C13 1.22678(15) 0.33506(15) 0.24249(13) 0.0249(3) Uani d . 1 1 . .
C C14 1.37336(15) 0.41100(17) 0.28825(13) 0.0313(4) Uani d . 1 1 . .
H H14 1.4285 0.3635 0.3066 0.038 Uiso calc R 1 1 . .
C C15 1.43893(15) 0.55614(17) 0.30705(13) 0.0311(3) Uani d . 1 1 . .
H H15 1.5393 0.6090 0.3392 0.037 Uiso calc R 1 1 . .
C C16 1.35845(15) 0.62377(16) 0.27904(13) 0.0292(3) Uani d . 1 1 . .
H H16 1.4036 0.7233 0.2899 0.035 Uiso calc R 1 1 . .
C C17 1.21141(14) 0.54688(14) 0.23495(12) 0.0231(3) Uani d . 1 1 . .
H H17 1.1568 0.5950 0.2170 0.028 Uiso calc R 1 1 . .
C C18 0.77955(13) 0.65020(13) 0.20813(12) 0.0194(3) Uani d . 1 1 . .
C C19 0.70373(15) 0.63013(15) 0.08661(13) 0.0266(3) Uani d . 1 1 . .
H H19 0.6793 0.5474 0.0224 0.032 Uiso calc R 1 1 . .
C C20 0.66390(17) 0.73115(18) 0.05937(15) 0.0378(4) Uani d . 1 1 . .
H H20 0.6110 0.7168 -0.0233 0.045 Uiso calc R 1 1 . .
C C21 0.70075(18) 0.85272(17) 0.15195(16) 0.0407(4) Uani d . 1 1 . .
H H21 0.6734 0.9217 0.1327 0.049 Uiso calc R 1 1 . .
C C22 0.77736(17) 0.87375(16) 0.27237(16) 0.0370(4) Uani d . 1 1 . .
H H22 0.8031 0.9577 0.3356 0.044 Uiso calc R 1 1 . .
C C23 0.81688(15) 0.77314(14) 0.30151(14) 0.0273(3) Uani d . 1 1 . .
H H23 0.8691 0.7877 0.3846 0.033 Uiso calc R 1 1 . .
H H4A 0.7078(16) 0.4471(16) 0.4696(13) 0.031(4) Uiso d . 1 1 . .
H H4B 0.8351(18) 0.5891(18) 0.5104(15) 0.052(5) Uiso d . 1 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
;
Cl Cl 0.1484 0.1585
; 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
C1 N1 N2 . . 113.49(10) ?
C1 N1 C3 . . 124.44(10) ?
N2 N1 C3 . . 121.98(10) ?
C2 N2 N1 . . 104.42(10) ?
C2 N3 C1 . . 109.50(10) ?
C2 N3 N4 . . 125.04(11) ?
C1 N3 N4 . . 125.45(10) ?
N3 N4 H4A . . 105.0(9) ?
N3 N4 H4B . . 104.9(9) ?
H4A N4 H4B . . 106.4(13) ?
N1 C1 N3 . . 102.56(10) ?
N1 C1 S1 . . 129.94(10) ?
N3 C1 S1 . . 127.46(9) ?
N2 C2 N3 . . 110.02(11) ?
N2 C2 C18 . . 124.06(11) ?
N3 C2 C18 . . 125.91(10) ?
N1 C3 C12 . . 110.60(10) ?
N1 C3 C4 . . 111.47(10) ?
C12 C3 C4 . . 112.37(10) ?
N1 C3 H3 . . 107.4 ?
C12 C3 H3 . . 107.4 ?
C4 C3 H3 . . 107.4 ?
C5 C4 C3 . . 112.76(10) ?
C5 C4 H4C . . 109.0 ?
C3 C4 H4C . . 109.0 ?
C5 C4 H4D . . 109.0 ?
C3 C4 H4D . . 109.0 ?
H4C C4 H4D . . 107.8 ?
O1 C5 C6 . . 121.17(12) ?
O1 C5 C4 . . 120.25(12) ?
C6 C5 C4 . . 118.56(10) ?
C11 C6 C7 . . 119.30(12) ?
C11 C6 C5 . . 121.73(12) ?
C7 C6 C5 . . 118.92(11) ?
C8 C7 C6 . . 120.06(13) ?
C8 C7 H7 . . 120.0 ?
C6 C7 H7 . . 120.0 ?
C7 C8 C9 . . 120.19(14) ?
C7 C8 H8 . . 119.9 ?
C9 C8 H8 . . 119.9 ?
C10 C9 C8 . . 120.20(14) ?
C10 C9 H9 . . 119.9 ?
C8 C9 H9 . . 119.9 ?
C9 C10 C11 . . 119.92(13) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C10 C11 C6 . . 120.33(13) ?
C10 C11 H11 . . 119.8 ?
C6 C11 H11 . . 119.8 ?
C13 C12 C17 . . 117.10(12) ?
C13 C12 C3 . . 121.22(12) ?
C17 C12 C3 . . 121.68(11) ?
C14 C13 C12 . . 121.95(13) ?
C14 C13 Cl1 . . 118.52(11) ?
C12 C13 Cl1 . . 119.53(11) ?
C15 C14 C13 . . 119.62(13) ?
C15 C14 H14 . . 120.2 ?
C13 C14 H14 . . 120.2 ?
C16 C15 C14 . . 119.78(14) ?
C16 C15 H15 . . 120.1 ?
C14 C15 H15 . . 120.1 ?
C15 C16 C17 . . 120.11(14) ?
C15 C16 H16 . . 119.9 ?
C17 C16 H16 . . 119.9 ?
C16 C17 C12 . . 121.41(12) ?
C16 C17 H17 . . 119.3 ?
C12 C17 H17 . . 119.3 ?
C19 C18 C23 . . 119.75(13) ?
C19 C18 C2 . . 119.19(12) ?
C23 C18 C2 . . 121.02(12) ?
C20 C19 C18 . . 119.86(14) ?
C20 C19 H19 . . 120.1 ?
C18 C19 H19 . . 120.1 ?
C21 C20 C19 . . 120.33(15) ?
C21 C20 H20 . . 119.8 ?
C19 C20 H20 . . 119.8 ?
C22 C21 C20 . . 120.00(14) ?
C22 C21 H21 . . 120.0 ?
C20 C21 H21 . . 120.0 ?
C21 C22 C23 . . 120.39(15) ?
C21 C22 H22 . . 119.8 ?
C23 C22 H22 . . 119.8 ?
C22 C23 C18 . . 119.67(14) ?
C22 C23 H23 . . 120.2 ?
C18 C23 H23 . . 120.2 ?
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 C1 . 1.6705(13) ?
Cl1 C13 . 1.7397(16) ?
O1 C5 . 1.2247(14) ?
N1 C1 . 1.3456(15) ?
N1 N2 . 1.3791(13) ?
N1 C3 . 1.4628(15) ?
N2 C2 . 1.3080(15) ?
N3 C2 . 1.3712(16) ?
N3 C1 . 1.3736(16) ?
N3 N4 . 1.4130(14) ?
N4 H4A . 0.918(15) ?
N4 H4B . 0.945(18) ?
C2 C18 . 1.4716(17) ?
C3 C12 . 1.5138(17) ?
C3 C4 . 1.5233(17) ?
C3 H3 . 1.0000 ?
C4 C5 . 1.5158(17) ?
C4 H4C . 0.9900 ?
C4 H4D . 0.9900 ?
C5 C6 . 1.4913(18) ?
C6 C11 . 1.3926(17) ?
C6 C7 . 1.3935(18) ?
C7 C8 . 1.3809(19) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.384(2) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.381(2) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.3828(18) ?
C10 H10 . 0.9500 ?
C11 H11 . 0.9500 ?
C12 C13 . 1.3886(17) ?
C12 C17 . 1.3926(18) ?
C13 C14 . 1.3847(19) ?
C14 C15 . 1.381(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.375(2) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.3871(18) ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
C18 C19 . 1.3910(18) ?
C18 C23 . 1.3974(18) ?
C19 C20 . 1.3861(19) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.383(2) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.382(2) ?
C21 H21 . 0.9500 ?
C22 C23 . 1.3865(19) ?
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 H4B S1 2_766 0.945(18) 2.714(17) 3.4928(17) 140.2(12) yes
C7 H7 O1 2_655 0.95 2.52 3.436(2) 161 yes
C21 H21 O1 1_565 0.95 2.53 3.415(2) 156 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
C1 N1 N2 C2 . . . . -0.53(14) ?
C3 N1 N2 C2 . . . . -177.29(11) ?
N2 N1 C1 N3 . . . . 0.61(13) ?
C3 N1 C1 N3 . . . . 177.27(11) ?
N2 N1 C1 S1 . . . . 178.26(9) ?
C3 N1 C1 S1 . . . . -5.07(19) ?
C2 N3 C1 N1 . . . . -0.45(13) ?
N4 N3 C1 N1 . . . . -179.92(11) ?
C2 N3 C1 S1 . . . . -178.18(10) ?
N4 N3 C1 S1 . . . . 2.35(19) ?
N1 N2 C2 N3 . . . . 0.21(13) ?
N1 N2 C2 C18 . . . . 179.04(11) ?
C1 N3 C2 N2 . . . . 0.15(14) ?
N4 N3 C2 N2 . . . . 179.62(11) ?
C1 N3 C2 C18 . . . . -178.65(12) ?
N4 N3 C2 C18 . . . . 0.8(2) ?
C1 N1 C3 C12 . . . . -87.95(14) ?
N2 N1 C3 C12 . . . . 88.45(13) ?
C1 N1 C3 C4 . . . . 146.26(11) ?
N2 N1 C3 C4 . . . . -37.34(15) ?
N1 C3 C4 C5 . . . . -63.58(13) ?
C12 C3 C4 C5 . . . . 171.62(10) ?
C3 C4 C5 O1 . . . . 4.68(17) ?
C3 C4 C5 C6 . . . . -173.49(10) ?
O1 C5 C6 C11 . . . . 179.54(12) ?
C4 C5 C6 C11 . . . . -2.31(17) ?
O1 C5 C6 C7 . . . . -3.03(18) ?
C4 C5 C6 C7 . . . . 175.12(11) ?
C11 C6 C7 C8 . . . . -0.16(19) ?
C5 C6 C7 C8 . . . . -177.66(12) ?
C6 C7 C8 C9 . . . . 0.6(2) ?
C7 C8 C9 C10 . . . . -0.6(2) ?
C8 C9 C10 C11 . . . . 0.2(2) ?
C9 C10 C11 C6 . . . . 0.3(2) ?
C7 C6 C11 C10 . . . . -0.26(19) ?
C5 C6 C11 C10 . . . . 177.17(11) ?
N1 C3 C12 C13 . . . . 145.32(12) ?
C4 C3 C12 C13 . . . . -89.41(14) ?
N1 C3 C12 C17 . . . . -34.62(16) ?
C4 C3 C12 C17 . . . . 90.66(14) ?
C17 C12 C13 C14 . . . . 1.71(19) ?
C3 C12 C13 C14 . . . . -178.22(12) ?
C17 C12 C13 Cl1 . . . . -178.59(9) ?
C3 C12 C13 Cl1 . . . . 1.47(17) ?
C12 C13 C14 C15 . . . . -1.0(2) ?
Cl1 C13 C14 C15 . . . . 179.27(10) ?
C13 C14 C15 C16 . . . . -0.6(2) ?
C14 C15 C16 C17 . . . . 1.5(2) ?
C15 C16 C17 C12 . . . . -0.8(2) ?
C13 C12 C17 C16 . . . . -0.78(19) ?
C3 C12 C17 C16 . . . . 179.15(11) ?
N2 C2 C18 C19 . . . . 45.75(18) ?
N3 C2 C18 C19 . . . . -135.61(13) ?
N2 C2 C18 C23 . . . . -131.78(13) ?
N3 C2 C18 C23 . . . . 46.86(18) ?
C23 C18 C19 C20 . . . . -0.91(19) ?
C2 C18 C19 C20 . . . . -178.47(12) ?
C18 C19 C20 C21 . . . . 0.8(2) ?
C19 C20 C21 C22 . . . . -0.1(2) ?
C20 C21 C22 C23 . . . . -0.4(2) ?
C21 C22 C23 C18 . . . . 0.4(2) ?
C19 C18 C23 C22 . . . . 0.32(19) ?
C2 C18 C23 C22 . . . . 177.84(11) ?
