#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/59/2205920.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_2205920
loop_
_publ_author_name
'Ngah, Nurziana'
'Shah, Nabihah M.'
'Kassim, Mohammad B.'
'Yamin, Bohari M.'
_publ_section_title
;
 2-(3-Benzoylthioureido)ethanoic acid dimethyl sulfoxide solvate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1910
_journal_page_last               o1912
_journal_paper_doi               10.1107/S1600536805016491
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C10 H10 N2 O3 S, C2 H6 O S'
_chemical_formula_moiety         'C10 H10 N2 O3 S, C2 H6 O S'
_chemical_formula_sum            'C12 H16 N2 O4 S2'
_chemical_formula_weight         316.39
_chemical_name_systematic
;
2-(3-Benzoylthioureido)ethanoic acid dimethyl sulfoxide solvate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.074(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.074(2)
_cell_length_b                   5.6289(12)
_cell_length_c                   13.969(3)
_cell_measurement_reflns_used    734
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      1.55
_cell_volume                     744.0(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 83.66
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_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  0.0135
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4157
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.55
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.371
_exptl_absorpt_correction_T_max  0.9396
_exptl_absorpt_correction_T_min  0.8537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.154
_refine_ls_abs_structure_details 'Flack (1983), 1117 Friedel pairs'
_refine_ls_abs_structure_Flack   0.06(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2725
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.037
_refine_ls_R_factor_gt           0.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0359P)²+0.1167P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.076
_refine_ls_wR_factor_ref         0.077
_reflns_number_gt                2537
_reflns_number_total             2725
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6512.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2205920
_cod_database_fobs_code          2205920
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_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_type_symbol
S1 -0.14142(6) 0.94424(12) 0.92765(5) 0.05230(17) Uani d . 1 S
S2 0.67896(7) 1.04731(12) 0.45849(5) 0.05832(19) Uani d . 1 S
O1 0.13275(16) 1.0048(3) 0.73050(12) 0.0572(5) Uani d . 1 O
O2 -0.10726(17) 1.5328(4) 0.65101(13) 0.0624(5) Uani d . 1 O
O3 -0.3078(2) 1.6498(4) 0.67026(15) 0.0645(5) Uani d . 1 O
H3A -0.3016 1.7618 0.6345 0.097 Uiso calc R 1 H
O4 0.66629(19) 1.0260(4) 0.56209(13) 0.0652(5) Uani d . 1 O
N1 0.07001(19) 0.8614(4) 0.86172(14) 0.0460(5) Uani d . 1 N
H1A 0.0931 0.7594 0.9105 0.055 Uiso calc R 1 H
N2 -0.07524(19) 1.1742(4) 0.78547(14) 0.0477(5) Uani d . 1 N
H2A -0.0216 1.1921 0.7496 0.057 Uiso calc R 1 H
C1 0.2733(2) 0.4817(4) 0.87876(16) 0.0475(6) Uani d . 1 C
H1 0.1942 0.4373 0.8943 0.057 Uiso calc R 1 H
C2 0.3903(3) 0.3343(5) 0.90534(18) 0.0559(6) Uani d . 1 C
H2 0.3903 0.1920 0.9391 0.067 Uiso calc R 1 H
C3 0.5071(3) 0.4003(5) 0.88129(18) 0.0565(7) Uani d . 1 C
H3 0.5862 0.3023 0.8995 0.068 Uiso calc R 1 H
C4 0.5075(3) 0.6076(5) 0.8312(2) 0.0569(7) Uani d . 1 C
H4 0.5864 0.6498 0.8148 0.068 Uiso calc R 1 H
C5 0.3913(2) 0.7550(5) 0.80467(19) 0.0500(6) Uani d . 1 C
H5 0.3918 0.8960 0.7701 0.060 Uiso calc R 1 H
C6 0.2731(2) 0.6935(4) 0.82944(16) 0.0418(5) Uani d . 1 C
C7 0.1531(2) 0.8658(4) 0.80102(17) 0.0437(5) Uani d . 1 C
C8 -0.0466(2) 1.0028(4) 0.85308(15) 0.0422(5) Uani d . 1 C
C9 -0.1931(2) 1.3342(5) 0.76879(18) 0.0502(6) Uani d . 1 C
H9A -0.1851 1.4132 0.8322 0.060 Uiso calc R 1 H
H9B -0.2806 1.2443 0.7468 0.060 Uiso calc R 1 H
C10 -0.1970(2) 1.5164(5) 0.68969(16) 0.0471(5) Uani d . 1 C
C11 0.8625(3) 1.0575(8) 0.4808(2) 0.0904(10) Uani d . 1 C
H11A 0.9002 1.2056 0.5127 0.136 Uiso calc R 1 H
H11B 0.8787 1.0438 0.4172 0.136 Uiso calc R 1 H
H11C 0.9084 0.9285 0.5247 0.136 Uiso calc R 1 H
C12 0.6429(4) 0.7620(6) 0.4031(3) 0.0857(10) Uani d . 1 C
H12A 0.7131 0.6520 0.4428 0.129 Uiso calc R 1 H
H12B 0.6449 0.7677 0.3349 0.129 Uiso calc R 1 H
H12C 0.5512 0.7111 0.4014 0.129 Uiso calc R 1 H
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
O4 S2 C12 106.10(15)
O4 S2 C11 105.22(13)
C12 S2 C11 98.74(19)
C10 O3 H3A 109.5
C7 N1 C8 127.5(2)
C7 N1 H1A 116.2
C8 N1 H1A 116.2
C8 N2 C9 122.71(19)
C8 N2 H2A 118.6
C9 N2 H2A 118.6
C6 C1 C2 120.5(2)
C6 C1 H1 119.7
C2 C1 H1 119.7
C3 C2 C1 119.5(3)
C3 C2 H2 120.3
C1 C2 H2 120.3
C4 C3 C2 120.6(2)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 120.2(2)
C3 C4 H4 119.9
C5 C4 H4 119.9
C4 C5 C6 120.2(2)
C4 C5 H5 119.9
C6 C5 H5 119.9
C1 C6 C5 119.0(2)
C1 C6 C7 123.9(2)
C5 C6 C7 117.1(2)
O1 C7 N1 122.6(2)
O1 C7 C6 121.87(19)
N1 C7 C6 115.5(2)
N2 C8 N1 117.03(19)
N2 C8 S1 124.27(17)
N1 C8 S1 118.70(17)
N2 C9 C10 110.97(18)
N2 C9 H9A 109.4
C10 C9 H9A 109.4
N2 C9 H9B 109.4
C10 C9 H9B 109.4
H9A C9 H9B 108.0
O2 C10 O3 125.9(2)
O2 C10 C9 123.3(2)
O3 C10 C9 110.75(19)
S2 C11 H11A 109.5
S2 C11 H11B 109.5
H11A C11 H11B 109.5
S2 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
S2 C12 H12A 109.5
S2 C12 H12B 109.5
H12A C12 H12B 109.5
S2 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 1.670(2) yes
S2 O4 1.5007(19) ?
S2 C12 1.765(3) ?
S2 C11 1.767(3) ?
O1 C7 1.219(3) yes
O2 C10 1.206(3) yes
O3 C10 1.294(3) yes
O3 H3A 0.8200 ?
N1 C7 1.381(3) yes
N1 C8 1.389(3) yes
N1 H1A 0.8600 ?
N2 C8 1.311(3) yes
N2 C9 1.444(3) yes
N2 H2A 0.8600 ?
C1 C6 1.377(3) ?
C1 C2 1.384(3) ?
C1 H1 0.9300 ?
C2 C3 1.380(4) ?
C2 H2 0.9300 ?
C3 C4 1.361(4) ?
C3 H3 0.9300 ?
C4 C5 1.378(3) ?
C4 H4 0.9300 ?
C5 C6 1.393(3) ?
C5 H5 0.9300 ?
C6 C7 1.493(3) ?
C9 C10 1.498(3) ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C11 H11A 0.9600 ?
C11 H11B 0.9600 ?
C11 H11C 0.9600 ?
C12 H12A 0.9600 ?
C12 H12B 0.9600 ?
C12 H12C 0.9600 ?
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 H2A O1 1_555 0.86 1.97 2.645(3) 134 yes
N2 H2A O2 1_555 0.86 2.35 2.700(3) 105 yes
N1 H1A S1 2_547 0.86 2.78 3.638(2) 174 no
O3 H3A O4 1_465 0.82 1.76 2.562(3) 164 yes
C1 H1 S1 2_547 0.93 2.72 3.404(2) 132 no
C4 H4 O3 1_645 0.93 2.59 3.383(4) 144 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
C6 C1 C2 C3 -0.5(3)
C1 C2 C3 C4 -0.5(4)
C2 C3 C4 C5 0.5(4)
C3 C4 C5 C6 0.4(4)
C2 C1 C6 C5 1.4(3)
C2 C1 C6 C7 -178.0(2)
C4 C5 C6 C1 -1.3(4)
C4 C5 C6 C7 178.2(2)
C8 N1 C7 O1 1.2(4)
C8 N1 C7 C6 179.4(2)
C1 C6 C7 O1 -154.6(2)
C5 C6 C7 O1 26.0(3)
C1 C6 C7 N1 27.2(3)
C5 C6 C7 N1 -152.2(2)
C9 N2 C8 N1 -179.9(2)
C9 N2 C8 S1 0.6(3)
C7 N1 C8 N2 -6.3(3)
C7 N1 C8 S1 173.25(19)
C8 N2 C9 C10 178.1(2)
N2 C9 C10 O2 -4.4(4)
N2 C9 C10 O3 175.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21129462
