##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# 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 journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_journal_date_recd_electronic     2020-02-25
_journal_date_accepted     2020-03-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2020
_journal_volume     76
_journal_issue      4
_journal_page_first     594
_journal_page_last     598
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989020002960
_journal_coeditor_code     ZQ2250
_publ_contact_author_name     'Sitthichok Mongkholkeaw'
_publ_contact_author_address
;
Department of Chemistry, Faculty of Science, Kasetsart University,
Bangkok, Thailand 10900
;
_publ_contact_author_email
;
fscibnw@ku.ac.th
;
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Crystal structure, Hirshfeld surface analysis and computational study of
2-chloro-N-[4-(methylsulfanyl)phenyl]acetamide
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Mongkholkeaw, Sitthichok' .
;
Department of Chemistry and Center of Excellence for Innovation in Chemistry,
Faculty of Science, Kasetsart University, Bangkok,
10900
Thailand
;
    'Songsasen, Apisit' .
;
Department of Chemistry and Center of Excellence for Innovation in Chemistry,
Faculty of Science, Kasetsart University, Bangkok,
10900
Thailand
;
    'Duangthongyou, Tanwawan' .
;
Department of Chemistry and Center of Excellence for Innovation in Chemistry,
Faculty of Science, Kasetsart University, Bangkok,
10900
Thailand
;
    'Chainok, Kittipong' .
;
Materials and Textile Technology, Faculty of Science and Technology,
Thammasat University, Pathum Thani, 12120
Thailand
;
    'Suramitr, Songwut' .
;
Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok,
10900
Thailand
;
    'Wattanathana, Worawat' .
;
Department of Materials Engineering, Faculty of Engineering,
Kasetsart University Bangkok, 10900
Thailand
;
    'Wannalerse, Boontana' .
;
Department of Chemistry and Center of Excellence for Innovation in Chemistry,
Faculty of Science, Kasetsart University, Bangkok,
10900
Thailand
;
_publ_section_synopsis
;
In the title compound, the amide functional group --C(=O)NH-- adopts a
trans conformation with the four atoms nearly coplanar. This
conformation promotes the formation of a C(4) hydrogen-bonded chain
propagating along the [010] direction.
;
_chemical_name_systematic
;
2-Chloro-N-[4-(methylsulfanyl)phenyl]acetamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C9 H10 Cl N O S'
_chemical_formula_sum     'C9 H10 Cl N O S'
_chemical_formula_iupac     'C9 H10 Cl N O S'
_chemical_formula_weight     215.69
_chemical_melting_point     ?
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P b c a'
_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _space_group_symop_operation_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'
_cell_length_a     9.6659(7)
_cell_length_b     14.0682(11)
_cell_length_c     14.4869(13)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1970.0(3)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     3435
_cell_measurement_theta_min     2.812
_cell_measurement_theta_max     26.174
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     'light brown'
_exptl_crystal_size_max     0.12
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.454
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     896
_exptl_absorpt_coefficient_mu     0.557
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_absorpt_correction_T_min     0.686
_exptl_absorpt_correction_T_max     0.746
_diffrn_ambient_temperature     296.0
_diffrn_source     ?
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     ?
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     21994
_diffrn_reflns_av_R_equivalents     0.0850
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_theta_min     2.812
_diffrn_reflns_theta_max     28.278
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     0
_refine_special_details     ?
_reflns_number_total     2438
_reflns_number_gt     1722
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0764
_refine_ls_R_factor_gt     0.0470
_refine_ls_wR_factor_gt     0.1112
_refine_ls_wR_factor_ref     0.1274
_refine_ls_goodness_of_fit_ref     1.022
_refine_ls_restrained_S_all     1.022
_refine_ls_number_reflns     2438
_refine_ls_number_parameters     123
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0510P)²+1.0616P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.511
_refine_diff_density_min     -0.413
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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
;
APEX2 (Bruker, 2016)
;
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
Olex2 (Dolomanov et al.,  2009) and
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
Olex2 (Dolomanov et al.,  2009) and
Mercury (Macrae et al.,  2020)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.44778(8) 0.40070(6) 0.90711(5) 0.0685(3) Uani d 1 . .
    S S1 0.52668(8) 0.73979(6) 0.33195(5) 0.0612(2) Uani d 1 . .
    O O1 0.36226(15) 0.51663(13) 0.74128(12) 0.0498(4) Uani d 1 . .
    N N1 0.58369(17) 0.53698(14) 0.69210(13) 0.0364(4) Uani d 1 . .
    H H1 0.663(3) 0.5277(17) 0.7080(18) 0.044 Uiso d 1 . .
    C C3 0.56559(19) 0.58332(15) 0.60636(15) 0.0333(4) Uani d 1 . .
    C C7 0.6767(2) 0.66353(17) 0.47953(16) 0.0423(5) Uani d 1 . .
    H H7 0.757186 0.685406 0.451533 0.051 Uiso calc 1 . .
    C C2 0.4871(2) 0.51212(16) 0.75445(16) 0.0370(5) Uani d 1 . .
    C C8 0.6844(2) 0.61629(17) 0.56270(16) 0.0394(5) Uani d 1 . .
    H H8 0.770224 0.606313 0.590012 0.047 Uiso calc 1 . .
    C C6 0.5498(2) 0.67873(16) 0.43719(16) 0.0392(5) Uani d 1 . .
    C C4 0.4384(2) 0.59718(17) 0.56390(17) 0.0404(5) Uani d 1 . .
    H H4 0.357922 0.574908 0.591632 0.048 Uiso calc 1 . .
    C C5 0.4319(2) 0.64410(18) 0.48042(17) 0.0440(5) Uani d 1 . .
    H H5 0.346335 0.652779 0.452346 0.053 Uiso calc 1 . .
    C C1 0.5487(2) 0.4838(2) 0.84654(17) 0.0477(6) Uani d 1 . .
    H H1A 0.559753 0.540211 0.884279 0.057 Uiso calc 1 . .
    H H1B 0.639951 0.457030 0.836228 0.057 Uiso calc 1 . .
    C C9 0.6958(3) 0.7388(2) 0.28174(19) 0.0566(7) Uani d 1 . .
    H H9A 0.691402 0.764360 0.220355 0.085 Uiso calc 1 . .
    H H9B 0.729678 0.674728 0.279361 0.085 Uiso calc 1 . .
    H H9C 0.757047 0.776878 0.318558 0.085 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    Cl1 C1 . 1.757(2) ?
    S1 C6 . 1.764(2) ?
    S1 C9 . 1.789(3) ?
    O1 C2 . 1.223(2) ?
    N1 H1 . 0.82(2) ?
    N1 C3 . 1.414(3) ?
    N1 C2 . 1.345(3) ?
    C3 C8 . 1.390(3) ?
    C3 C4 . 1.388(3) ?
    C7 H7 . 0.9300 ?
    C7 C8 . 1.378(3) ?
    C7 C6 . 1.388(3) ?
    C2 C1 . 1.515(3) ?
    C8 H8 . 0.9300 ?
    C6 C5 . 1.388(3) ?
    C4 H4 . 0.9300 ?
    C4 C5 . 1.379(3) ?
    C5 H5 . 0.9300 ?
    C1 H1A . 0.9700 ?
    C1 H1B . 0.9700 ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
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
    C6 S1 C9 . . 103.42(12) ?
    C3 N1 H1 . . 116.1(19) ?
    C2 N1 H1 . . 115.1(18) ?
    C2 N1 C3 . . 128.60(18) ?
    C8 C3 N1 . . 116.83(18) ?
    C4 C3 N1 . . 124.31(18) ?
    C4 C3 C8 . . 118.9(2) ?
    C8 C7 H7 . . 119.7 ?
    C8 C7 C6 . . 120.6(2) ?
    C6 C7 H7 . . 119.7 ?
    O1 C2 N1 . . 124.5(2) ?
    O1 C2 C1 . . 122.62(19) ?
    N1 C2 C1 . . 112.76(18) ?
    C3 C8 H8 . . 119.5 ?
    C7 C8 C3 . . 120.9(2) ?
    C7 C8 H8 . . 119.5 ?
    C7 C6 S1 . . 124.67(18) ?
    C7 C6 C5 . . 118.1(2) ?
    C5 C6 S1 . . 117.19(17) ?
    C3 C4 H4 . . 120.1 ?
    C5 C4 C3 . . 119.7(2) ?
    C5 C4 H4 . . 120.1 ?
    C6 C5 H5 . . 119.1 ?
    C4 C5 C6 . . 121.8(2) ?
    C4 C5 H5 . . 119.1 ?
    Cl1 C1 H1A . . 108.9 ?
    Cl1 C1 H1B . . 108.9 ?
    C2 C1 Cl1 . . 113.36(16) ?
    C2 C1 H1A . . 108.9 ?
    C2 C1 H1B . . 108.9 ?
    H1A C1 H1B . . 107.7 ?
    S1 C9 H9A . . 109.5 ?
    S1 C9 H9B . . 109.5 ?
    S1 C9 H9C . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
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
    S1 C6 C5 C4 . . . . -178.58(19) ?
    O1 C2 C1 Cl1 . . . . 32.9(3) ?
    N1 C3 C8 C7 . . . . -179.1(2) ?
    N1 C3 C4 C5 . . . . 179.4(2) ?
    N1 C2 C1 Cl1 . . . . -150.97(18) ?
    C3 N1 C2 O1 . . . . 8.9(4) ?
    C3 N1 C2 C1 . . . . -167.2(2) ?
    C3 C4 C5 C6 . . . . -0.3(4) ?
    C7 C6 C5 C4 . . . . 1.1(4) ?
    C2 N1 C3 C8 . . . . 168.6(2) ?
    C2 N1 C3 C4 . . . . -11.7(4) ?
    C8 C3 C4 C5 . . . . -0.8(3) ?
    C8 C7 C6 S1 . . . . 178.92(18) ?
    C8 C7 C6 C5 . . . . -0.7(4) ?
    C6 C7 C8 C3 . . . . -0.4(4) ?
    C4 C3 C8 C7 . . . . 1.2(3) ?
    C9 S1 C6 C7 . . . . 18.0(2) ?
    C9 S1 C6 C5 . . . . -162.3(2) ?
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 H1 O1 6_657 0.82(2) 2.06(3) 2.875(2) 174(3) yes
    C1 H1B O1 6_657 0.97 2.57 3.319(3) 135 yes
    C4 H4 O1 . 0.93 2.32 2.903(3) 121 yes
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     0.936
_shelx_estimated_absorpt_T_max     0.957
