#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/57/2235751.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_2235751
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Kumar, Sharatha'
_publ_section_title
;
 3-Acetyl-1-(2,3-dichlorophenyl)thiourea
;
_journal_coeditor_code           BT5964
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2353
_journal_paper_doi               10.1107/S1600536812030176
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C9 H8 Cl2 N2 O S'
_chemical_formula_moiety         'C9 H8 Cl2 N2 O S'
_chemical_formula_sum            'C9 H8 Cl2 N2 O S'
_chemical_formula_weight         263.13
_chemical_name_systematic
;
3-Acetyl-1-(2,3-dichlorophenyl)thiourea
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.044(6)
_cell_angle_beta                 91.099(6)
_cell_angle_gamma                100.208(6)
_cell_formula_units_Z            4
_cell_length_a                   7.8475(6)
_cell_length_b                   9.5987(7)
_cell_length_c                   15.1410(10)
_cell_measurement_reflns_used    4895
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.71
_cell_measurement_theta_min      2.54
_cell_volume                     1122.24(14)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using omega
;
_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  0.0105
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7971
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.54
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  0.7772
_exptl_absorpt_correction_T_min  0.7279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.720
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4578
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0403P)²+0.8845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1057
_reflns_number_gt                3885
_reflns_number_total             4578
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5964.cif
_cod_data_source_block           I
_cod_database_code               2235751
_cod_database_fobs_code          2235751
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
Cl Cl1 0.39378(10) 0.64301(8) -0.04620(5) 0.0675(2) Uani d . 1 1
Cl Cl2 0.51017(13) 0.81095(13) -0.21801(5) 0.0956(3) Uani d . 1 1
S S1 0.86892(8) 0.69266(7) 0.15722(5) 0.05361(18) Uani d . 1 1
O O1 0.3014(2) 0.6735(2) 0.21951(13) 0.0687(6) Uani d . 1 1
N N1 0.5647(3) 0.7665(2) 0.11819(13) 0.0457(5) Uani d D 1 1
H H1N 0.458(2) 0.754(3) 0.1305(18) 0.055 Uiso d D 1 1
N N2 0.5747(2) 0.6306(2) 0.24233(12) 0.0397(4) Uani d D 1 1
H H2N 0.639(3) 0.591(3) 0.2760(15) 0.048 Uiso d D 1 1
C C1 0.6232(3) 0.8420(2) 0.04055(15) 0.0412(5) Uani d . 1 1
C C2 0.5487(3) 0.7949(3) -0.04025(16) 0.0441(5) Uani d . 1 1
C C3 0.5999(3) 0.8705(3) -0.11636(17) 0.0526(6) Uani d . 1 1
C C4 0.7246(3) 0.9910(3) -0.11191(19) 0.0561(7) Uani d . 1 1
H H4 0.7589 1.0412 -0.1630 0.067 Uiso calc R 1 1
C C5 0.7983(3) 1.0369(3) -0.0314(2) 0.0564(7) Uani d . 1 1
H H5 0.8827 1.1182 -0.0283 0.068 Uiso calc R 1 1
C C6 0.7479(3) 0.9632(3) 0.04515(18) 0.0512(6) Uani d . 1 1
H H6 0.7977 0.9951 0.0993 0.061 Uiso calc R 1 1
C C7 0.6603(3) 0.6990(2) 0.17092(14) 0.0374(5) Uani d . 1 1
C C8 0.4039(3) 0.6220(3) 0.26475(16) 0.0451(5) Uani d . 1 1
C C9 0.3545(3) 0.5463(3) 0.34875(18) 0.0607(7) Uani d . 1 1
H H9A 0.2336 0.5439 0.3587 0.073 Uiso calc R 1 1
H H9B 0.4214 0.5949 0.3969 0.073 Uiso calc R 1 1
H H9C 0.3768 0.4513 0.3449 0.073 Uiso calc R 1 1
Cl Cl3 0.68592(11) -0.06753(7) 0.35412(5) 0.0693(2) Uani d . 1 1
Cl Cl4 0.60530(13) -0.20874(9) 0.53971(7) 0.0884(3) Uani d . 1 1
S S2 0.78757(8) 0.45828(6) 0.39216(4) 0.04733(16) Uani d . 1 1
O O2 1.0172(3) 0.1780(2) 0.20337(14) 0.0772(6) Uani d . 1 1
N N3 0.9002(3) 0.2163(2) 0.36075(13) 0.0453(5) Uani d D 1 1
H H3N 0.932(3) 0.169(3) 0.3223(15) 0.054 Uiso d D 1 1
N N4 0.9362(3) 0.3818(2) 0.24969(13) 0.0432(4) Uani d D 1 1
H H4N 0.924(3) 0.463(2) 0.2336(17) 0.052 Uiso d D 1 1
C C10 0.8602(3) 0.1564(2) 0.44498(15) 0.0405(5) Uani d . 1 1
C C11 0.7626(3) 0.0208(2) 0.44964(16) 0.0440(5) Uani d . 1 1
C C12 0.7286(3) -0.0417(3) 0.53190(18) 0.0531(6) Uani d . 1 1
C C13 0.7920(4) 0.0296(3) 0.60792(18) 0.0591(7) Uani d . 1 1
H H13 0.7690 -0.0126 0.6627 0.071 Uiso calc R 1 1
C C14 0.8890(4) 0.1627(3) 0.60259(17) 0.0570(7) Uani d . 1 1
H H14 0.9317 0.2107 0.6540 0.068 Uiso calc R 1 1
C C15 0.9241(3) 0.2264(3) 0.52160(16) 0.0494(6) Uani d . 1 1
H H15 0.9908 0.3166 0.5187 0.059 Uiso calc R 1 1
C C16 0.8777(3) 0.3440(2) 0.33372(14) 0.0378(5) Uani d . 1 1
C C17 1.0071(3) 0.3013(3) 0.18971(17) 0.0509(6) Uani d . 1 1
C C18 1.0707(4) 0.3771(3) 0.10721(18) 0.0633(7) Uani d . 1 1
H H18A 1.0801 0.3093 0.0618 0.076 Uiso calc R 1 1
H H18B 1.1822 0.4344 0.1187 0.076 Uiso calc R 1 1
H H18C 0.9906 0.4364 0.0882 0.076 Uiso calc R 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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 N1 C1 125.50(19)
C7 N1 H1N 114.5(19)
C1 N1 H1N 119.6(19)
C8 N2 C7 128.45(19)
C8 N2 H2N 117.7(18)
C7 N2 H2N 113.8(18)
C6 C1 C2 120.1(2)
C6 C1 N1 121.0(2)
C2 C1 N1 118.9(2)
C1 C2 C3 119.6(2)
C1 C2 Cl1 120.12(18)
C3 C2 Cl1 120.3(2)
C4 C3 C2 120.4(2)
C4 C3 Cl2 119.6(2)
C2 C3 Cl2 120.0(2)
C5 C4 C3 119.6(2)
C5 C4 H4 120.2
C3 C4 H4 120.2
C4 C5 C6 120.6(2)
C4 C5 H5 119.7
C6 C5 H5 119.7
C1 C6 C5 119.7(3)
C1 C6 H6 120.2
C5 C6 H6 120.2
N1 C7 N2 115.39(19)
N1 C7 S1 125.13(17)
N2 C7 S1 119.48(16)
O1 C8 N2 122.4(2)
O1 C8 C9 122.6(2)
N2 C8 C9 115.0(2)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C16 N3 C10 126.43(19)
C16 N3 H3N 114(2)
C10 N3 H3N 120(2)
C17 N4 C16 128.0(2)
C17 N4 H4N 116.8(19)
C16 N4 H4N 115.1(19)
C15 C10 C11 119.8(2)
C15 C10 N3 121.4(2)
C11 C10 N3 118.8(2)
C10 C11 C12 119.3(2)
C10 C11 Cl3 119.74(18)
C12 C11 Cl3 120.92(19)
C13 C12 C11 120.4(2)
C13 C12 Cl4 119.3(2)
C11 C12 Cl4 120.3(2)
C14 C13 C12 119.8(2)
C14 C13 H13 120.1
C12 C13 H13 120.1
C13 C14 C15 120.7(2)
C13 C14 H14 119.7
C15 C14 H14 119.7
C10 C15 C14 120.0(2)
C10 C15 H15 120.0
C14 C15 H15 120.0
N3 C16 N4 115.5(2)
N3 C16 S2 125.53(17)
N4 C16 S2 118.93(16)
O2 C17 N4 122.3(2)
O2 C17 C18 122.8(2)
N4 C17 C18 114.9(2)
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.726(2)
Cl2 C3 1.734(3)
S1 C7 1.666(2)
O1 C8 1.217(3)
N1 C7 1.330(3)
N1 C1 1.422(3)
N1 H1N 0.846(17)
N2 C8 1.378(3)
N2 C7 1.387(3)
N2 H2N 0.843(16)
C1 C6 1.382(3)
C1 C2 1.386(3)
C2 C3 1.390(3)
C3 C4 1.378(4)
C4 C5 1.377(4)
C4 H4 0.9300
C5 C6 1.385(4)
C5 H5 0.9300
C6 H6 0.9300
C8 C9 1.489(3)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
Cl3 C11 1.719(2)
Cl4 C12 1.725(3)
S2 C16 1.669(2)
O2 C17 1.218(3)
N3 C16 1.332(3)
N3 C10 1.417(3)
N3 H3N 0.808(17)
N4 C17 1.379(3)
N4 C16 1.388(3)
N4 H4N 0.836(16)
C10 C15 1.381(3)
C10 C11 1.391(3)
C11 C12 1.392(3)
C12 C13 1.377(4)
C13 C14 1.370(4)
C13 H13 0.9300
C14 C15 1.381(4)
C14 H14 0.9300
C15 H15 0.9300
C17 C18 1.495(4)
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1N O1 0.846(17) 1.91(2) 2.625(3) 141(3)
N2 H2N S2 0.843(16) 2.559(17) 3.393(2) 171(2)
N3 H3N O2 0.808(17) 1.93(2) 2.619(3) 143(3)
N4 H4N S1 0.836(16) 2.591(17) 3.418(2) 170(2)
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
C7 N1 C1 C6 -65.8(3)
C7 N1 C1 C2 116.5(3)
C6 C1 C2 C3 -0.1(3)
N1 C1 C2 C3 177.6(2)
C6 C1 C2 Cl1 179.65(18)
N1 C1 C2 Cl1 -2.6(3)
C1 C2 C3 C4 0.4(4)
Cl1 C2 C3 C4 -179.44(19)
C1 C2 C3 Cl2 178.94(18)
Cl1 C2 C3 Cl2 -0.9(3)
C2 C3 C4 C5 -0.2(4)
Cl2 C3 C4 C5 -178.8(2)
C3 C4 C5 C6 -0.2(4)
C2 C1 C6 C5 -0.2(4)
N1 C1 C6 C5 -177.9(2)
C4 C5 C6 C1 0.4(4)
C1 N1 C7 N2 -179.0(2)
C1 N1 C7 S1 1.4(4)
C8 N2 C7 N1 1.1(3)
C8 N2 C7 S1 -179.31(19)
C7 N2 C8 O1 2.5(4)
C7 N2 C8 C9 -177.0(2)
C16 N3 C10 C15 -53.7(3)
C16 N3 C10 C11 130.0(2)
C15 C10 C11 C12 0.9(3)
N3 C10 C11 C12 177.3(2)
C15 C10 C11 Cl3 -178.97(19)
N3 C10 C11 Cl3 -2.6(3)
C10 C11 C12 C13 -0.4(4)
Cl3 C11 C12 C13 179.4(2)
C10 C11 C12 Cl4 179.07(18)
Cl3 C11 C12 Cl4 -1.1(3)
C11 C12 C13 C14 0.0(4)
Cl4 C12 C13 C14 -179.5(2)
C12 C13 C14 C15 0.0(4)
C11 C10 C15 C14 -0.9(4)
N3 C10 C15 C14 -177.2(2)
C13 C14 C15 C10 0.5(4)
C10 N3 C16 N4 176.4(2)
C10 N3 C16 S2 -3.3(4)
C17 N4 C16 N3 3.3(3)
C17 N4 C16 S2 -177.0(2)
C16 N4 C17 O2 4.5(4)
C16 N4 C17 C18 -175.3(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1031786
