#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/41/2234196.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_2234196
loop_
_publ_author_name
'Shahwar, Durre'
'Tahir, M. Nawaz'
'Chohan, Muhammad Mansha'
'Ahmad, Naeem'
'Raza, M. Asam'
_publ_section_title
;
 3-Acetyl-1-(3-chlorophenyl)thiourea
;
_journal_coeditor_code           GK2470
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1189
_journal_paper_doi               10.1107/S1600536812012147
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C9 H9 Cl N2 O S'
_chemical_formula_moiety         'C9 H9 Cl N2 O S'
_chemical_formula_sum            'C9 H9 Cl N2 O S'
_chemical_formula_weight         228.69
_chemical_name_systematic
;
3-Acetyl-1-(3-chlorophenyl)thiourea
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 122.651(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.3980(14)
_cell_length_b                   4.1768(2)
_cell_length_c                   20.2635(11)
_cell_measurement_reflns_used    1464
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.10
_cell_measurement_theta_min      2.05
_cell_volume                     2023.69(18)
_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 8.10
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7045
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.05
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.550
_exptl_absorpt_correction_T_max  0.872
_exptl_absorpt_correction_T_min  0.868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.228
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1775
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0340
_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)+(0.0527P)²+1.9073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1085
_reflns_number_gt                1450
_reflns_number_total             1745
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2470.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2234196
_cod_database_fobs_code          2234196
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 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_thermal_displace_type
_atom_site_occupancy
_atom_site_disorder_group
Cl Cl1 0.27943(3) 0.9289(2) 0.34233(4) 0.0593(3) Uani 1.000 -16
S S1 0.08011(2) 0.46913(17) 0.10724(3) 0.0436(2) Uani 1.000 -16
O O1 -0.03091(7) 1.0496(5) 0.16023(11) 0.0610(7) Uani 1.000 -16
N N1 0.06728(7) 0.7792(5) 0.21108(10) 0.0383(6) Uani 1.000 -16
N N2 -0.00930(7) 0.7704(5) 0.08375(10) 0.0353(6) Uani 1.000 -16
C C1 0.12315(9) 0.7158(6) 0.27507(12) 0.0334(7) Uani 1.000 -16
C C2 0.16843(9) 0.8388(6) 0.27522(13) 0.0375(8) Uani 1.000 -16
C C3 0.22127(9) 0.7785(6) 0.33950(13) 0.0375(7) Uani 1.000 -16
C C4 0.22942(10) 0.6054(7) 0.40248(14) 0.0461(8) Uani 1.000 -16
C C5 0.18373(11) 0.4900(7) 0.40138(16) 0.0520(9) Uani 1.000 -16
C C6 0.13025(10) 0.5409(6) 0.33725(14) 0.0422(8) Uani 1.000 -16
C C7 0.04606(9) 0.6845(5) 0.13794(12) 0.0328(7) Uani 1.000 -16
C C8 -0.04474(9) 0.9441(6) 0.09596(14) 0.0395(8) Uani 1.000 -16
C C9 -0.10196(10) 0.9910(7) 0.02487(15) 0.0480(9) Uani 1.000 -16
H H1 0.04591 0.88682 0.22087 0.0459 Uiso 1.000 -16
H H2 -0.02292 0.70566 0.03650 0.0424 Uiso 1.000 -16
H H3 0.16340 0.95861 0.23319 0.0450 Uiso 1.000 -16
H H4 0.26537 0.56692 0.44526 0.0553 Uiso 1.000 -16
H H5 0.18883 0.37642 0.44424 0.0624 Uiso 1.000 -16
H H6 0.09947 0.45780 0.33622 0.0506 Uiso 1.000 -16
H H9A -0.09942 1.10785 -0.01390 0.0720 Uiso 1.000 -16
H H9B -0.12438 1.10907 0.03877 0.0720 Uiso 1.000 -16
H H9C -0.11887 0.78623 0.00402 0.0720 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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C7 124.9(2) no
C7 N2 C8 128.42(19) no
C1 N1 H1 118.00 no
C7 N1 H1 118.00 no
C7 N2 H2 116.00 no
C8 N2 H2 116.00 no
N1 C1 C2 120.5(2) no
N1 C1 C6 118.1(3) no
C2 C1 C6 121.3(2) no
C1 C2 C3 118.1(2) no
Cl1 C3 C4 118.6(2) no
C2 C3 C4 121.7(3) no
Cl1 C3 C2 119.68(19) no
C3 C4 C5 119.1(3) no
C4 C5 C6 120.7(3) no
C1 C6 C5 119.2(3) no
S1 C7 N1 125.0(2) no
S1 C7 N2 118.65(16) no
N1 C7 N2 116.3(2) no
O1 C8 C9 122.5(3) no
N2 C8 C9 114.8(2) no
O1 C8 N2 122.7(2) no
C1 C2 H3 121.00 no
C3 C2 H3 121.00 no
C3 C4 H4 120.00 no
C5 C4 H4 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
C8 C9 H9A 109.00 no
C8 C9 H9B 109.00 no
C8 C9 H9C 109.00 no
H9A C9 H9B 109.00 no
H9A C9 H9C 109.00 no
H9B C9 H9C 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C3 1.739(3) no
S1 C7 1.667(3) no
O1 C8 1.222(3) no
N1 C1 1.431(3) no
N1 C7 1.324(3) no
N2 C7 1.394(3) no
N2 C8 1.367(4) no
N1 H1 0.8600 no
N2 H2 0.8600 no
C1 C6 1.374(3) no
C1 C2 1.383(4) no
C2 C3 1.379(4) no
C3 C4 1.373(4) no
C4 C5 1.373(5) no
C5 C6 1.382(4) no
C8 C9 1.493(4) no
C2 H3 0.9300 no
C4 H4 0.9300 no
C5 H5 0.9300 no
C6 H6 0.9300 no
C9 H9A 0.9600 no
C9 H9B 0.9600 no
C9 H9C 0.9600 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
N1 H1 O1 . 0.86 1.96 2.648(3) 136 yes
N2 H2 S1 3_565 0.86 2.56 3.4095(18) 170 yes
C9 H9A S1 3_575 0.96 2.85 3.799(3) 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
C7 N1 C1 C2 63.5(3) no
C7 N1 C1 C6 -119.0(3) no
C1 N1 C7 S1 1.1(4) no
C1 N1 C7 N2 -179.9(2) no
C8 N2 C7 S1 179.9(2) no
C8 N2 C7 N1 0.8(4) no
C7 N2 C8 O1 -0.3(4) no
C7 N2 C8 C9 -179.5(2) no
N1 C1 C2 C3 178.0(2) no
C6 C1 C2 C3 0.6(4) no
N1 C1 C6 C5 -176.9(2) no
C2 C1 C6 C5 0.6(4) no
C1 C2 C3 Cl1 -179.9(2) no
C1 C2 C3 C4 -0.8(4) no
Cl1 C3 C4 C5 179.0(2) no
C2 C3 C4 C5 -0.1(4) no
C3 C4 C5 C6 1.3(4) no
C4 C5 C6 C1 -1.6(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 844258
