##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'PLATON <TABLE ACC> option'
_journal_date_recd_electronic     2016-07-04
_journal_date_accepted     2016-07-13
_journal_name_full     'IUCrData'
_journal_year     2016
_journal_volume     1
_journal_issue      7
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314616011391
_journal_coeditor_code     HG4010
_publ_contact_author_name     'Dr. M. M. M. Abdoh'
_publ_contact_author_address
;
Department of Physics,
Faculty of Science,
An Najah National
University, Nablus
West Bank,
Palestinian Territories
;
_publ_contact_author_email     muneer@najah.edu
_publ_contact_author_phone         .97E-305
_publ_section_title
;
2-[(5-Amino-1,3,4-thiadiazol-2-yl)sulfanyl]-N-(4-chlorophenyl)acetamide
;
loop_
    _publ_author_name
    _publ_author_address
    'Madan Kumar, S.'
;
PURSE Lab, Mangalagangotri
Mangalore University
Mangaluru 574 199
India
;
    'Madhu Kumar, D. J.'
;
Department of Post-Graduate and Research In Chemistry,
Mangalagangori
Mangalore University
India
;
    'Harish, K. S.'
;
Department of Physics,
Sheshadripuram PU college
Mysore 570 017
India
;
    'Jagadeesha, Prasad D.'
;
Department of Post-Graduate and Research In Chemistry,
Mangalagangori
Mangalore University
India
;
    'Byrappa, K.'
;
Department of Material Science,
Mangalore University
Mangaluru 574 199
India
;
    'Abdoh, M. M. M.'
;
Department of Physics,
Faculty of Science,
An Najah National University, Nablus
West Bank,
Palestinian Territories
;
_publ_section_synopsis
;
The molecular and crystal structure of
2-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanyl]-N-(4-chlorophenyl)acetamide
is reported. The crystal structure is stabilized through intermolecular
N---H...N and N---H...O hydrogen bonds.
;
data_I
_database_code_depnum_ccdc_archive 'CCDC 1428528'
_chemical_name_systematic
;\
2-[(5-Amino-1,3,4-thiadiazol-2-yl)sulfanyl]-\
N-(4-chlorophenyl)acetamide
;
_chemical_formula_moiety     'C10 H9 Cl N4 O S2'
_chemical_formula_sum     'C10 H9 Cl N4 O S2'
_chemical_formula_iupac     'C10 H9 Cl N4 O S2'
_chemical_formula_weight     300.78
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_id
    _space_group_symop_operation_xyz
    1 x,y,z
    2 -x,1/2+y,1/2-z
    3 -x,-y,-z
    4 x,1/2-y,1/2+z
_cell_length_a     26.379(5)
_cell_length_b     4.7704(8)
_cell_length_c     10.1866(18)
_cell_angle_alpha     90
_cell_angle_beta     96.996(7)
_cell_angle_gamma     90
_cell_volume     1272.3(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2881
_cell_measurement_theta_min     3.1
_cell_measurement_theta_max     27.5
_cell_measurement_temperature     293
_cell_special_details
;
;
_exptl_crystal_description     'block'
_exptl_crystal_colour     'brown'
_exptl_crystal_size_max     0.320
_exptl_crystal_size_mid     0.230
_exptl_crystal_size_min     0.120
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.570
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'Not Measured'
_exptl_crystal_F_000     616
_exptl_absorpt_coefficient_mu     0.620
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(NUMABS; Rigaku 1999)
;
_exptl_absorpt_correction_T_min     0.843
_exptl_absorpt_correction_T_max     0.928
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_source     ?
_diffrn_radiation_monochromator     ?
_diffrn_measurement_device_type     'Rigaku Saturn724+'
_diffrn_measurement_device     'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_method     'profile data from ω-scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10559
_diffrn_reflns_av_R_equivalents     0.0663
_diffrn_reflns_theta_min     3.11
_diffrn_reflns_theta_max     27.49
_diffrn_reflns_theta_full     25.24
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -34
_diffrn_reflns_limit_h_max     34
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     5
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_reflns_reduction_process
;
;
_refine_special_details     ?
_reflns_number_total     2881
_reflns_number_gt     2019
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0790
_refine_ls_R_factor_gt     0.0513
_refine_ls_wR_factor_gt     0.1144
_refine_ls_wR_factor_ref     0.1269
_refine_ls_goodness_of_fit_ref     1.055
_refine_ls_restrained_S_all     1.055
_refine_ls_number_reflns     2881
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[Σ²(Fo²)+(0.0490P)²+0.4848P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.340
_refine_diff_density_min     -0.340
_refine_ls_extinction_method     'none'
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     .
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'
    Cl Cl 0.1484 0.1585 ' 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'
_computing_data_collection
;
CrystalClear SM Expert (Rigaku, 2011)
;
_computing_cell_refinement
;
CrystalClear SM Expert (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear SM Expert (Rigaku, 2011)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.45400(4) 0.6782(3) 0.30886(13) 0.1062(6) Uani d . 1.000 . .
    S S1 0.10780(3) 0.59735(16) 0.36162(7) 0.0389(2) Uani d . 1.000 . .
    S S2 0.15876(3) 0.17391(16) 0.55874(7) 0.0409(2) Uani d . 1.000 . .
    O O1 0.24709(8) 0.7463(4) 0.6213(2) 0.0543(8) Uani d . 1.000 . .
    N N1 0.08143(8) 0.5253(5) 0.5913(2) 0.0386(8) Uani d . 1.000 . .
    N N2 0.04937(8) 0.7301(5) 0.5344(2) 0.0372(7) Uani d . 1.000 . .
    N N3 0.03064(8) 0.9734(6) 0.3363(2) 0.0422(8) Uani d . 1.000 . .
    N N11 0.27991(9) 0.3229(5) 0.5821(3) 0.0476(9) Uani d . 1.000 . .
    C C1 0.05795(10) 0.7883(6) 0.4124(2) 0.0331(8) Uani d . 1.000 . .
    C C2 0.11406(10) 0.4409(6) 0.5160(2) 0.0348(9) Uani d . 1.000 . .
    C C3 0.20296(10) 0.3442(6) 0.6846(3) 0.0394(9) Uani d . 1.000 . .
    C C4 0.24508(10) 0.4915(6) 0.6270(3) 0.0382(9) Uani d . 1.000 . .
    C C5 0.32186(11) 0.4125(6) 0.5165(3) 0.0435(10) Uani d . 1.000 . .
    C C6 0.31545(12) 0.6126(7) 0.4193(3) 0.0554(11) Uani d . 1.000 . .
    C C7 0.35637(14) 0.6942(9) 0.3561(4) 0.0704(14) Uani d . 1.000 . .
    C C8 0.40275(13) 0.5755(9) 0.3893(4) 0.0638(14) Uani d . 1.000 . .
    C C9 0.40974(13) 0.3734(9) 0.4832(4) 0.0719(15) Uani d . 1.000 . .
    C C10 0.36869(13) 0.2904(8) 0.5480(4) 0.0654(16) Uani d . 1.000 . .
    H H3A 0.00600 1.06190 0.36610 0.0510 Uiso c R 1.000 . .
    H H3B 0.03760 1.00480 0.25730 0.0510 Uiso c R 1.000 . .
    H H3C 0.18440 0.47870 0.73200 0.0470 Uiso c R 1.000 . .
    H H3D 0.21750 0.20480 0.74750 0.0470 Uiso c R 1.000 . .
    H H6 0.28350 0.69330 0.39610 0.0670 Uiso c R 1.000 . .
    H H7 0.35210 0.83100 0.29060 0.0840 Uiso c R 1.000 . .
    H H9 0.44160 0.29080 0.50410 0.0860 Uiso c R 1.000 . .
    H H10 0.37310 0.15200 0.61270 0.0790 Uiso c R 1.000 . .
    H H11 0.27660 0.14560 0.59390 0.0570 Uiso c R 1.000 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Cl1 0.0674(7) 0.1549(13) 0.1040(9) -0.0259(7) 0.0419(6) 0.0066(8)
    S1 0.0432(4) 0.0475(5) 0.0289(3) 0.0042(3) 0.0162(3) -0.0013(3)
    S2 0.0409(4) 0.0356(4) 0.0466(4) -0.0003(3) 0.0076(3) -0.0044(3)
    O1 0.0574(13) 0.0294(12) 0.0784(17) 0.0021(10) 0.0176(12) -0.0010(11)
    N1 0.0427(13) 0.0462(15) 0.0290(11) 0.0023(11) 0.0127(10) 0.0006(11)
    N2 0.0389(12) 0.0488(15) 0.0259(11) 0.0054(10) 0.0127(9) 0.0016(10)
    N3 0.0479(14) 0.0551(17) 0.0260(11) 0.0120(12) 0.0140(10) 0.0046(11)
    N11 0.0482(15) 0.0326(14) 0.0654(17) -0.0006(11) 0.0206(12) 0.0012(13)
    C1 0.0339(13) 0.0420(17) 0.0251(12) -0.0035(12) 0.0105(10) -0.0049(12)
    C2 0.0353(13) 0.0394(17) 0.0315(14) -0.0064(12) 0.0109(11) -0.0019(12)
    C3 0.0434(15) 0.0429(18) 0.0328(14) 0.0029(13) 0.0086(12) 0.0016(13)
    C4 0.0378(14) 0.0358(17) 0.0399(15) 0.0025(12) 0.0000(12) -0.0009(13)
    C5 0.0424(16) 0.0399(18) 0.0497(18) -0.0041(13) 0.0116(13) -0.0058(15)
    C6 0.0480(18) 0.065(2) 0.054(2) -0.0009(16) 0.0099(15) 0.0080(18)
    C7 0.066(2) 0.087(3) 0.060(2) -0.006(2) 0.0153(18) 0.020(2)
    C8 0.051(2) 0.082(3) 0.061(2) -0.0152(19) 0.0178(17) -0.006(2)
    C9 0.0408(18) 0.091(3) 0.086(3) 0.0049(19) 0.0159(18) -0.003(2)
    C10 0.050(2) 0.072(3) 0.077(3) 0.0151(18) 0.0187(18) 0.019(2)
_geom_special_details
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl1 C8 . . 1.735(4) no
    S1 C1 . . 1.730(3) no
    S1 C2 . . 1.730(2) no
    S2 C2 . . 1.754(3) no
    S2 C3 . . 1.816(3) no
    O1 C4 . . 1.218(3) no
    N1 N2 . . 1.373(3) no
    N1 C2 . . 1.285(3) no
    N2 C1 . . 1.320(3) no
    N3 C1 . . 1.328(4) no
    N11 C4 . . 1.343(4) no
    N11 C5 . . 1.426(4) no
    C3 C4 . . 1.494(4) no
    N3 H3B . . 0.8600 no
    N3 H3A . . 0.8600 no
    C5 C10 . . 1.368(5) no
    C5 C6 . . 1.371(4) no
    C6 C7 . . 1.379(5) no
    C7 C8 . . 1.353(5) no
    C8 C9 . . 1.355(6) no
    C9 C10 . . 1.393(5) no
    N11 H11 . . 0.8600 no
    C3 H3C . . 0.9700 no
    C3 H3D . . 0.9700 no
    C6 H6 . . 0.9300 no
    C7 H7 . . 0.9300 no
    C9 H9 . . 0.9300 no
    C10 H10 . . 0.9300 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 S1 C2 . . . 86.98(12) no
    C2 S2 C3 . . . 101.82(13) no
    N2 N1 C2 . . . 113.2(2) no
    N1 N2 C1 . . . 112.3(2) no
    C4 N11 C5 . . . 125.6(2) no
    S1 C1 N2 . . . 113.3(2) no
    S1 C1 N3 . . . 123.62(17) no
    N2 C1 N3 . . . 123.1(2) no
    S1 C2 S2 . . . 121.71(14) no
    S1 C2 N1 . . . 114.2(2) no
    S2 C2 N1 . . . 123.92(18) no
    S2 C3 C4 . . . 112.2(2) no
    H3A N3 H3B . . . 120.00 no
    C1 N3 H3B . . . 120.00 no
    C1 N3 H3A . . . 120.00 no
    N11 C4 C3 . . . 115.1(2) no
    O1 C4 C3 . . . 121.8(3) no
    O1 C4 N11 . . . 123.1(3) no
    N11 C5 C6 . . . 120.8(3) no
    N11 C5 C10 . . . 119.5(3) no
    C6 C5 C10 . . . 119.6(3) no
    C5 C6 C7 . . . 120.0(3) no
    C6 C7 C8 . . . 120.0(4) no
    Cl1 C8 C9 . . . 119.2(3) no
    Cl1 C8 C7 . . . 119.8(3) no
    C7 C8 C9 . . . 121.0(4) no
    C8 C9 C10 . . . 119.4(3) no
    C5 C10 C9 . . . 120.0(3) no
    C4 N11 H11 . . . 117.00 no
    C5 N11 H11 . . . 117.00 no
    S2 C3 H3C . . . 109.00 no
    S2 C3 H3D . . . 109.00 no
    C4 C3 H3C . . . 109.00 no
    C4 C3 H3D . . . 109.00 no
    H3C C3 H3D . . . 108.00 no
    C5 C6 H6 . . . 120.00 no
    C7 C6 H6 . . . 120.00 no
    C6 C7 H7 . . . 120.00 no
    C8 C7 H7 . . . 120.00 no
    C8 C9 H9 . . . 120.00 no
    C10 C9 H9 . . . 120.00 no
    C5 C10 H10 . . . 120.00 no
    C9 C10 H10 . . . 120.00 no
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
    C2 S1 C1 N2 . . . . 0.4(2) no
    C2 S1 C1 N3 . . . . -179.1(3) no
    C1 S1 C2 S2 . . . . 176.98(19) no
    C1 S1 C2 N1 . . . . 1.0(2) no
    C3 S2 C2 S1 . . . . 112.82(18) no
    C3 S2 C2 N1 . . . . -71.6(3) no
    C2 S2 C3 C4 . . . . -89.6(2) no
    C2 N1 N2 C1 . . . . 2.3(3) no
    N2 N1 C2 S1 . . . . -2.1(3) no
    N2 N1 C2 S2 . . . . -177.95(19) no
    N1 N2 C1 S1 . . . . -1.5(3) no
    N1 N2 C1 N3 . . . . 177.9(2) no
    C5 N11 C4 O1 . . . . -3.4(5) no
    C5 N11 C4 C3 . . . . 176.3(3) no
    C4 N11 C5 C6 . . . . -44.4(5) no
    C4 N11 C5 C10 . . . . 137.8(3) no
    S2 C3 C4 O1 . . . . 107.9(3) no
    S2 C3 C4 N11 . . . . -71.8(3) no
    N11 C5 C6 C7 . . . . -179.3(3) no
    C10 C5 C6 C7 . . . . -1.5(5) no
    N11 C5 C10 C9 . . . . 179.1(3) no
    C6 C5 C10 C9 . . . . 1.2(5) no
    C5 C6 C7 C8 . . . . 0.5(6) no
    C6 C7 C8 Cl1 . . . . 179.7(3) no
    C6 C7 C8 C9 . . . . 0.9(6) no
    Cl1 C8 C9 C10 . . . . 180.0(3) no
    C7 C8 C9 C10 . . . . -1.1(6) no
    C8 C9 C10 C5 . . . . 0.1(6) no
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
    N3 H3A N2 3_576 0.8600 2.1200 2.978(3) 172.00 yes
    N3 H3B N1 4_564 0.8600 2.1700 2.973(3) 156.00 yes
    N3 H3B N2 4_564 0.8600 2.5800 3.319(3) 144.00 yes
    N11 H11 O1 1_545 0.8600 2.0900 2.926(3) 164.00 yes
_iucr_refine_instructions_details
;
;
