#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/50/2235061.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_2235061
loop_
_publ_author_name
'Murtaza, Shahzad'
'Tahir, M. Nawaz'
'Tariq, Javaria'
'Abbas, Aadil'
'Kausar, Naghmana'
_publ_section_title
;
 2-[(2-Aminophenyl)sulfanyl]-N-(4-methoxyphenyl)acetamide
;
_journal_coeditor_code           HB6821
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1968
_journal_paper_doi               10.1107/S1600536812024178
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C15 H16 N2 O2 S'
_chemical_formula_moiety         'C15 H16 N2 O2 S'
_chemical_formula_sum            'C15 H16 N2 O2 S'
_chemical_formula_weight         288.36
_chemical_name_systematic
;
2-[(2-Aminophenyl)sulfanyl]-N-(4-methoxyphenyl)acetamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 95.506(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9935(16)
_cell_length_b                   4.7990(4)
_cell_length_c                   23.433(3)
_cell_measurement_reflns_used    1525
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      1.57
_cell_volume                     1454.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.80
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_sigmaI/netI    0.0721
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11532
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.57
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            gray
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.201
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0435P)²+0.1361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                1525
_reflns_number_total             2845
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6821.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2235061
_cod_database_fobs_code          2235061
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_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
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_occupancy
_atom_site_disorder_group
S S1 0.67008(6) 0.17005(14) 0.17482(3) 0.0513(3) Uani 1.000 -16
O O1 0.06467(19) 0.2484(5) -0.05402(11) 0.0942(11) Uani 1.000 -16
O O2 0.48924(15) 0.0421(3) 0.09749(9) 0.0565(8) Uani 1.000 -16
N N1 0.43663(19) 0.4757(4) 0.07298(10) 0.0480(9) Uani 1.000 -16
N N2 0.5848(2) 0.4083(5) 0.27906(12) 0.0763(12) Uani 1.000 -16
C C1 0.3429(2) 0.4077(5) 0.03984(12) 0.0423(10) Uani 1.000 -16
C C2 0.2538(3) 0.5466(6) 0.04982(14) 0.0578(11) Uani 1.000 -16
C C3 0.1626(3) 0.4868(7) 0.01822(16) 0.0750(14) Uani 1.000 -16
C C4 0.1593(3) 0.2887(7) -0.02452(14) 0.0590(12) Uani 1.000 -16
C C5 0.2468(3) 0.1500(6) -0.03442(13) 0.0569(11) Uani 1.000 -16
C C6 0.3386(2) 0.2099(6) -0.00259(12) 0.0496(11) Uani 1.000 -16
C C7 0.0533(3) 0.0393(9) -0.09623(17) 0.1020(17) Uani 1.000 -16
C C8 0.5023(2) 0.2953(5) 0.09956(11) 0.0423(10) Uani 1.000 -16
C C9 0.5937(2) 0.4227(5) 0.13308(13) 0.0606(11) Uani 1.000 -16
C C10 0.7332(2) 0.4001(5) 0.22519(13) 0.0467(11) Uani 1.000 -16
C C11 0.6839(3) 0.4890(6) 0.27227(14) 0.0520(11) Uani 1.000 -16
C C12 0.7355(3) 0.6709(7) 0.31078(15) 0.0743(14) Uani 1.000 -16
C C13 0.8316(3) 0.7639(7) 0.30315(18) 0.0838(17) Uani 1.000 -16
C C14 0.8816(3) 0.6776(7) 0.25769(19) 0.0842(16) Uani 1.000 -16
C C15 0.8321(3) 0.4935(7) 0.21861(16) 0.0654(14) Uani 1.000 -16
H H1 0.45235 0.64944 0.07614 0.0576 Uiso 1.000 -16
H H2 0.25569 0.68219 0.07826 0.0696 Uiso 1.000 -16
H H2A 0.55421 0.47092 0.30741 0.0916 Uiso 1.000 -16
H H2B 0.55300 0.29502 0.25497 0.0916 Uiso 1.000 -16
H H3 0.10255 0.58008 0.02558 0.0897 Uiso 1.000 -16
H H5 0.24472 0.01413 -0.06280 0.0680 Uiso 1.000 -16
H H6 0.39837 0.11528 -0.00991 0.0595 Uiso 1.000 -16
H H7A 0.07153 -0.13793 -0.07913 0.1529 Uiso 1.000 -16
H H7B 0.09784 0.07889 -0.12562 0.1529 Uiso 1.000 -16
H H7C -0.01719 0.03419 -0.11275 0.1529 Uiso 1.000 -16
H H9A 0.57022 0.56384 0.15846 0.0724 Uiso 1.000 -16
H H9B 0.63654 0.51361 0.10692 0.0724 Uiso 1.000 -16
H H12 0.70365 0.73062 0.34250 0.0890 Uiso 1.000 -16
H H13 0.86413 0.88868 0.32937 0.1003 Uiso 1.000 -16
H H14 0.94784 0.74134 0.25299 0.1009 Uiso 1.000 -16
H H15 0.86569 0.43201 0.18764 0.0783 Uiso 1.000 -16
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 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C9 S1 C10 98.01(12) no
C4 O1 C7 119.1(3) no
C1 N1 C8 125.9(2) no
C8 N1 H1 117.00 no
C1 N1 H1 117.00 no
C11 N2 H2A 120.00 no
H2A N2 H2B 120.00 no
C11 N2 H2B 120.00 no
N1 C1 C6 122.0(2) no
N1 C1 C2 119.2(2) no
C2 C1 C6 118.8(3) no
C1 C2 C3 120.4(3) no
C2 C3 C4 120.2(3) no
C3 C4 C5 119.6(3) no
O1 C4 C3 115.4(3) no
O1 C4 C5 124.9(3) no
C4 C5 C6 120.2(3) no
C1 C6 C5 120.7(3) no
O2 C8 N1 123.2(2) no
O2 C8 C9 121.8(2) no
N1 C8 C9 115.0(2) no
S1 C9 C8 112.38(17) no
S1 C10 C15 120.4(2) no
C11 C10 C15 119.4(3) no
S1 C10 C11 120.2(2) no
N2 C11 C12 120.4(3) no
C10 C11 C12 118.6(3) no
N2 C11 C10 120.9(3) no
C11 C12 C13 121.2(3) no
C12 C13 C14 121.2(4) no
C13 C14 C15 119.0(4) no
C10 C15 C14 120.7(3) no
C1 C2 H2 120.00 no
C3 C2 H2 120.00 no
C2 C3 H3 120.00 no
C4 C3 H3 120.00 no
C4 C5 H5 120.00 no
C6 C5 H5 120.00 no
C1 C6 H6 120.00 no
C5 C6 H6 120.00 no
O1 C7 H7A 109.00 no
O1 C7 H7B 109.00 no
O1 C7 H7C 109.00 no
H7A C7 H7B 109.00 no
H7A C7 H7C 109.00 no
H7B C7 H7C 109.00 no
S1 C9 H9A 109.00 no
S1 C9 H9B 109.00 no
C8 C9 H9A 109.00 no
C8 C9 H9B 109.00 no
H9A C9 H9B 108.00 no
C11 C12 H12 119.00 no
C13 C12 H12 119.00 no
C12 C13 H13 119.00 no
C14 C13 H13 119.00 no
C13 C14 H14 121.00 no
C15 C14 H14 121.00 no
C10 C15 H15 120.00 no
C14 C15 H15 120.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C9 1.796(3) no
S1 C10 1.760(3) no
O1 C4 1.365(5) no
O1 C7 1.407(5) no
O2 C8 1.227(3) no
N1 C1 1.418(4) no
N1 C8 1.328(3) no
N2 C11 1.369(5) no
N1 H1 0.8600 no
N2 H2A 0.8600 no
N2 H2B 0.8600 no
C1 C2 1.375(4) no
C1 C6 1.372(4) no
C2 C3 1.366(5) no
C3 C4 1.379(5) no
C4 C5 1.357(5) no
C5 C6 1.375(5) no
C8 C9 1.491(4) no
C10 C15 1.384(5) no
C10 C11 1.395(4) no
C11 C12 1.382(5) no
C12 C13 1.354(5) no
C13 C14 1.364(6) no
C14 C15 1.386(5) no
C2 H2 0.9300 no
C3 H3 0.9300 no
C5 H5 0.9300 no
C6 H6 0.9300 no
C7 H7A 0.9600 no
C7 H7B 0.9600 no
C7 H7C 0.9600 no
C9 H9A 0.9700 no
C9 H9B 0.9700 no
C12 H12 0.9300 no
C13 H13 0.9300 no
C14 H14 0.9300 no
C15 H15 0.9300 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
N2 H2B S1 . 0.86 2.60 3.004(3) 110 yes
N1 H1 O2 1_565 0.86 2.00 2.848(3) 170 yes
N2 H2A O2 2_655 0.86 2.38 3.200(3) 161 yes
C3 H3 O1 3_565 0.93 2.47 3.393(5) 170 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
_geom_torsion_publ_flag
C10 S1 C9 C8 -158.8(2) no
C9 S1 C10 C11 82.1(2) no
C9 S1 C10 C15 -98.1(3) no
C7 O1 C4 C3 -176.6(3) no
C7 O1 C4 C5 3.3(5) no
C8 N1 C1 C2 131.0(3) no
C8 N1 C1 C6 -50.0(4) no
C1 N1 C8 O2 1.2(4) no
C1 N1 C8 C9 -178.2(2) no
N1 C1 C2 C3 179.5(3) no
C6 C1 C2 C3 0.4(4) no
N1 C1 C6 C5 -179.4(3) no
C2 C1 C6 C5 -0.4(4) no
C1 C2 C3 C4 -0.8(5) no
C2 C3 C4 O1 -179.0(3) no
C2 C3 C4 C5 1.1(5) no
O1 C4 C5 C6 179.1(3) no
C3 C4 C5 C6 -1.0(5) no
C4 C5 C6 C1 0.7(5) no
O2 C8 C9 S1 -6.7(3) no
N1 C8 C9 S1 172.7(2) no
S1 C10 C11 N2 -2.5(4) no
S1 C10 C11 C12 -179.6(2) no
C15 C10 C11 N2 177.8(3) no
C15 C10 C11 C12 0.6(4) no
S1 C10 C15 C14 179.1(3) no
C11 C10 C15 C14 -1.1(5) no
N2 C11 C12 C13 -176.7(3) no
C10 C11 C12 C13 0.5(5) no
C11 C12 C13 C14 -1.1(6) no
C12 C13 C14 C15 0.6(6) no
C13 C14 C15 C10 0.5(5) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 751069
2 PubChem 859478
