#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/93/2229382.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_2229382
loop_
_publ_author_name
'Pérez, Hiram'
'Corrêa, Rodrigo S.'
'Plutín, Ana María'
'Álvarez, Anislay'
'Mascarenhas, Yvonne'
_publ_section_title
;
 N-Benzoyl-N',N'-dimethylthiourea
;
_journal_coeditor_code           GK2336
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o647
_journal_paper_doi               10.1107/S1600536811005137
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C10 H12 N2 O S'
_chemical_formula_moiety         'C10 H12 N2 O S'
_chemical_formula_sum            'C10 H12 N2 O S'
_chemical_formula_weight         208.28
_chemical_name_systematic
;
N-Benzoyl-N',N'-dimethylthiourea
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 102.768(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8602(9)
_cell_length_b                   5.5590(6)
_cell_length_c                   18.6864(10)
_cell_measurement_reflns_used    1912
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.72
_cell_measurement_theta_min      3.48
_cell_volume                     1100.24(16)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor 1997)'
_computing_data_collection       'COLLECT (Enraf--Nonius, 2000)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor 1997)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7078
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         26.72
_diffrn_reflns_theta_min         3.48
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   '(Coppens et al., 1965)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.271
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2282
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0587P)²+0.1899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1202
_reflns_number_gt                1762
_reflns_number_total             2282
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gk2336.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2229382
_cod_database_fobs_code          2229382
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_disorder_assembly
_atom_site_disorder_group
C C1 0.55382(16) 0.7917(3) 0.35288(9) 0.0475(4) Uani d . 1 . .
C C2 0.38501(16) 0.6859(3) 0.41573(8) 0.0459(4) Uani d . 1 . .
C C3 0.69073(16) 0.8469(3) 0.36576(9) 0.0484(4) Uani d . 1 . .
C C4 0.7314(2) 1.0217(4) 0.32357(10) 0.0638(5) Uani d . 1 . .
H H4 0.6731 1.103 0.2878 0.077 Uiso calc R 1 . .
C C5 0.8583(2) 1.0756(5) 0.33449(13) 0.0778(6) Uani d . 1 . .
H H5 0.8853 1.1951 0.3067 0.093 Uiso calc R 1 . .
C C6 0.9442(2) 0.9537(5) 0.38608(14) 0.0822(7) Uani d . 1 . .
H H6 1.0296 0.9899 0.393 0.099 Uiso calc R 1 . .
C C7 0.90569(19) 0.7787(5) 0.42771(14) 0.0785(6) Uani d . 1 . .
H H7 0.965 0.6965 0.4627 0.094 Uiso calc R 1 . .
C C8 0.77898(18) 0.7235(4) 0.41797(11) 0.0608(5) Uani d . 1 . .
H H8 0.7529 0.6042 0.4463 0.073 Uiso calc R 1 . .
C C9 0.3971(3) 0.3391(4) 0.33595(14) 0.0806(7) Uani d . 1 . .
H H9A 0.4844 0.3341 0.3609 0.121 Uiso calc R 1 . .
H H9B 0.3906 0.3891 0.2861 0.121 Uiso calc R 1 . .
H H9C 0.3607 0.182 0.3366 0.121 Uiso calc R 1 . .
C C10 0.19432(19) 0.4648(5) 0.36413(12) 0.0753(6) Uani d . 1 . .
H H10A 0.1503 0.6153 0.3619 0.113 Uiso calc R 1 . .
H H10B 0.1803 0.373 0.4051 0.113 Uiso calc R 1 . .
H H10C 0.1636 0.3765 0.3196 0.113 Uiso calc R 1 . .
N N1 0.51125(13) 0.7326(3) 0.41555(8) 0.0485(4) Uani d . 1 . .
N N2 0.32963(14) 0.5100(3) 0.37299(8) 0.0557(4) Uani d . 1 . .
O O1 0.48381(12) 0.7991(3) 0.29255(6) 0.0623(4) Uani d . 1 . .
S S1 0.31430(4) 0.84543(10) 0.47135(3) 0.0602(2) Uani d . 1 . .
H H1 0.5514(19) 0.802(4) 0.4545(11) 0.066(6) Uiso d . 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 0 '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 0.006 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 N1 . . 122.28(16) ?
O1 C1 C3 . . 122.89(15) ?
N1 C1 C3 . . 114.83(14) ?
N2 C2 N1 . . 116.90(15) ?
N2 C2 S1 . . 123.85(14) ?
N1 C2 S1 . . 119.21(12) ?
C4 C3 C8 . . 119.31(17) ?
C4 C3 C1 . . 119.15(16) ?
C8 C3 C1 . . 121.52(16) ?
C5 C4 C3 . . 120.14(19) ?
C5 C4 H4 . . 119.9 ?
C3 C4 H4 . . 119.9 ?
C6 C5 C4 . . 120.0(2) ?
C6 C5 H5 . . 120 ?
C4 C5 H5 . . 120 ?
C5 C6 C7 . . 120.5(2) ?
C5 C6 H6 . . 119.7 ?
C7 C6 H6 . . 119.7 ?
C6 C7 C8 . . 120.3(2) ?
C6 C7 H7 . . 119.9 ?
C8 C7 H7 . . 119.9 ?
C7 C8 C3 . . 119.70(19) ?
C7 C8 H8 . . 120.1 ?
C3 C8 H8 . . 120.1 ?
N2 C9 H9A . . 109.5 ?
N2 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
N2 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
N2 C10 H10A . . 109.5 ?
N2 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
N2 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C1 N1 C2 . . 123.76(14) ?
C1 N1 H1 . . 114.1(14) ?
C2 N1 H1 . . 113.5(14) ?
C2 N2 C10 . . 120.48(16) ?
C2 N2 C9 . . 123.91(17) ?
C10 N2 C9 . . 115.48(17) ?
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
C1 O1 . 1.2133(19) n
C1 N1 . 1.390(2) n
C1 C3 . 1.485(2) ?
C2 N2 . 1.321(2) n
C2 N1 . 1.396(2) n
C2 S1 . 1.6759(17) n
C3 C4 . 1.384(3) ?
C3 C8 . 1.388(3) ?
C4 C5 . 1.381(3) ?
C4 H4 . 0.93 ?
C5 C6 . 1.364(3) ?
C5 H5 . 0.93 ?
C6 C7 . 1.368(3) ?
C6 H6 . 0.93 ?
C7 C8 . 1.382(3) ?
C7 H7 . 0.93 ?
C8 H8 . 0.93 ?
C9 N2 . 1.464(3) n
C9 H9A . 0.96 ?
C9 H9B . 0.96 ?
C9 H9C . 0.96 ?
C10 N2 . 1.464(2) n
C10 H10A . 0.96 ?
C10 H10B . 0.96 ?
C10 H10C . 0.96 ?
N1 H1 . 0.85(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 S1 3_676 0.85(2) 2.65(2) 3.4335(17) 154.2(18) y
C9 H9A N1 . 0.96 2.43 2.778(3) 101 n
C9 H9B O1 . 0.96 2.49 2.902(3) 106 n
C10 H10C O1 2_545 0.96 2.38 3.265(3) 153 y
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
O1 C1 C3 C4 . . . . 34.5(3) ?
N1 C1 C3 C4 . . . . -144.94(17) ?
O1 C1 C3 C8 . . . . -144.04(19) ?
N1 C1 C3 C8 . . . . 36.5(2) ?
C8 C3 C4 C5 . . . . -1.3(3) ?
C1 C3 C4 C5 . . . . -179.87(19) ?
C3 C4 C5 C6 . . . . 1.1(3) ?
C4 C5 C6 C7 . . . . -0.4(4) ?
C5 C6 C7 C8 . . . . -0.1(4) ?
C6 C7 C8 C3 . . . . -0.1(4) ?
C4 C3 C8 C7 . . . . 0.8(3) ?
C1 C3 C8 C7 . . . . 179.32(19) ?
O1 C1 N1 C2 . . . . -2.6(3) ?
C3 C1 N1 C2 . . . . 176.89(15) ?
N2 C2 N1 C1 . . . . 57.9(2) ?
S1 C2 N1 C1 . . . . -124.37(16) ?
N1 C2 N2 C10 . . . . -173.79(17) ?
S1 C2 N2 C10 . . . . 8.6(2) ?
N1 C2 N2 C9 . . . . 10.6(3) ?
S1 C2 N2 C9 . . . . -167.03(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 720163
