#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/20/2202085.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_2202085
loop_
_publ_author_name
'Zhang, You-Ming'
'Xian, Liang'
'Wei, Tai-Bao'
'Cai, Li-Xiang'
_publ_section_title
;
 N-Benzoyl-N'-(2-hydroxyethyl)thiourea
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o817
_journal_page_last               o819
_journal_paper_doi               10.1107/S1600536803010213
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C10 H12 N2 O2 S'
_chemical_formula_moiety         'C10 H12 N2 O2 S'
_chemical_formula_sum            'C10 H12 N2 O2 S'
_chemical_formula_weight         224.28
_chemical_name_systematic
;
N-benzoyl-N'-(2-hydroxyethyl)-Thiourea
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 102.44(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.083(3)
_cell_length_b                   4.5490(10)
_cell_length_c                   14.279(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      10
_cell_volume                     1083.6(4)
_computing_cell_refinement       'CAD-4 SDP/VAX  (Enraf-Nonius, 1989)'
_computing_data_collection
'CAD-4 Operations Manual (Enraf-Nonius, 1977)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1997b)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0910
_diffrn_reflns_av_sigmaI/netI    0.0670
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3712
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         1.22
_diffrn_standards_decay_%        0.2
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.244
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0620P)²+0.3405P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1380
_reflns_number_gt                1564
_reflns_number_total             1908
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na6226.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/c'
_cod_database_code               2202085
_cod_database_fobs_code          2202085
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S1 0.08551(3) 0.45894(16) 0.95174(4) 0.0592(3) Uani d . 1 . . S
N1 0.21786(9) 0.7725(4) 0.97426(12) 0.0454(4) Uani d . 1 . . N
H1A 0.2015 0.8143 1.0226 0.050 Uiso d R 1 . . H
N2 0.18859(10) 0.4902(4) 0.83755(12) 0.0469(5) Uani d . 1 . . N
H2A 0.2362 0.5520 0.8277 0.080 Uiso d R 1 . . H
O1 0.31531(10) 0.8284(5) 0.89041(12) 0.0657(5) Uani d . 1 . . O
O2 0.13441(10) 0.6596(4) 0.64428(11) 0.0625(5) Uani d . 1 . . O
H2B 0.1046 0.7612 0.6008 0.080 Uiso d R 1 . . H
C1 0.40592(16) 1.1841(8) 1.0294(2) 0.0750(8) Uani d . 1 . . C
H1B 0.4265 1.1317 0.9742 0.080 Uiso d R 1 . . H
C2 0.45035(19) 1.3645(9) 1.0993(3) 0.0909(11) Uani d . 1 . . C
H2C 0.5019 1.4339 1.0925 0.080 Uiso d R 1 . . H
C3 0.42197(18) 1.4399(7) 1.1765(3) 0.0836(10) Uani d . 1 . . C
H3A 0.4531 1.5631 1.2253 0.080 Uiso d R 1 . . H
C4 0.3497(2) 1.3431(10) 1.1847(3) 0.1034(13) Uani d . 1 . . C
H4A 0.3288 1.4008 1.2391 0.080 Uiso d R 1 . . H
C5 0.30506(16) 1.1622(9) 1.1165(2) 0.0890(11) Uani d . 1 . . C
H5A 0.2540 1.0911 1.1246 0.080 Uiso d R 1 . . H
C6 0.33226(12) 1.0822(5) 1.03780(16) 0.0498(5) Uani d . 1 . . C
C7 0.28909(12) 0.8850(5) 0.96115(15) 0.0473(5) Uani d . 1 . . C
C8 0.16700(12) 0.5742(5) 0.91664(14) 0.0423(5) Uani d . 1 . . C
C9 0.14017(13) 0.3015(5) 0.76514(16) 0.0524(6) Uani d . 1 . . C
H9A 0.1087 0.1731 0.7956 0.080 Uiso d R 1 . . H
H9B 0.1745 0.1819 0.7359 0.080 Uiso d R 1 . . H
C10 0.08607(15) 0.4766(6) 0.68919(17) 0.0584(6) Uani d . 1 . . C
H10A 0.0544 0.3474 0.6429 0.080 Uiso d R 1 . . H
H10B 0.0506 0.5943 0.7173 0.080 Uiso d R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0512(4) 0.0748(5) 0.0566(4) -0.0166(3) 0.0227(3) -0.0127(3)
N1 0.0428(8) 0.0551(11) 0.0403(9) -0.0020(8) 0.0137(7) -0.0035(8)
N2 0.0482(9) 0.0519(11) 0.0429(10) -0.0024(8) 0.0153(7) -0.0031(8)
O1 0.0589(9) 0.0844(13) 0.0607(10) -0.0164(9) 0.0282(8) -0.0106(10)
O2 0.0696(10) 0.0715(12) 0.0477(9) 0.0072(9) 0.0154(7) 0.0058(8)
C1 0.0632(14) 0.094(2) 0.0660(16) -0.0273(15) 0.0104(12) 0.0060(16)
C2 0.0765(18) 0.099(2) 0.088(2) -0.0425(19) -0.0017(16) 0.009(2)
C3 0.0782(19) 0.069(2) 0.087(2) -0.0107(15) -0.0191(17) -0.0104(17)
C4 0.0780(19) 0.134(3) 0.099(2) -0.020(2) 0.0203(17) -0.061(3)
C5 0.0563(14) 0.124(3) 0.090(2) -0.0232(17) 0.0237(14) -0.051(2)
C6 0.0430(10) 0.0473(13) 0.0560(13) 0.0012(9) 0.0037(9) 0.0053(10)
C7 0.0436(10) 0.0492(12) 0.0496(12) 0.0016(10) 0.0108(9) 0.0051(10)
C8 0.0420(10) 0.0451(11) 0.0397(10) 0.0044(9) 0.0087(8) 0.0032(9)
C9 0.0607(12) 0.0494(13) 0.0498(12) -0.0055(10) 0.0183(10) -0.0094(10)
C10 0.0574(13) 0.0689(16) 0.0484(12) -0.0060(11) 0.0101(10) -0.0110(11)
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
C7 N1 C8 128.40(18)
C7 N1 H1A 120.1
C8 N1 H1A 111.4
C8 N2 C9 123.93(18)
C8 N2 H2A 118.2
C9 N2 H2A 117.9
C10 O2 H2B 109.5
C6 C1 C2 120.5(3)
C6 C1 H1B 119.5
C2 C1 H1B 119.9
C3 C2 C1 120.3(3)
C3 C2 H2C 120.1
C1 C2 H2C 119.6
C4 C3 C2 119.4(3)
C4 C3 H3A 120.4
C2 C3 H3A 120.2
C3 C4 C5 121.1(3)
C3 C4 H4A 119.5
C5 C4 H4A 119.4
C6 C5 C4 120.8(3)
C6 C5 H5A 119.5
C4 C5 H5A 119.8
C5 C6 C1 117.8(3)
C5 C6 C7 124.7(2)
C1 C6 C7 117.4(2)
O1 C7 N1 122.1(2)
O1 C7 C6 121.8(2)
N1 C7 C6 116.13(19)
N2 C8 N1 116.11(18)
N2 C8 S1 125.02(17)
N1 C8 S1 118.87(15)
N2 C9 C10 111.6(2)
N2 C9 H9A 109.0
C10 C9 H9A 109.5
N2 C9 H9B 109.7
C10 C9 H9B 109.1
H9A C9 H9B 107.9
O2 C10 C9 108.1(2)
O2 C10 H10A 110.1
C9 C10 H10A 110.0
O2 C10 H10B 110.1
C9 C10 H10B 110.0
H10A C10 H10B 108.5
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
S1 C8 . 1.663(2) ?
N1 C7 . 1.370(3) ?
N1 C8 . 1.392(3) ?
N1 H1A . 0.8206 ?
N2 C8 . 1.318(3) ?
N2 C9 . 1.457(3) ?
N2 H2A . 0.9001 ?
O1 C7 . 1.217(3) ?
O2 C10 . 1.419(3) ?
O2 H2B . 0.8501 ?
C1 C6 . 1.370(3) ?
C1 C2 . 1.385(5) ?
C1 H1B . 0.9597 ?
C2 C3 . 1.341(5) ?
C2 H2C . 0.9599 ?
C3 C4 . 1.339(5) ?
C3 H3A . 0.9601 ?
C4 C5 . 1.373(4) ?
C4 H4A . 0.9598 ?
C5 C6 . 1.355(4) ?
C5 H5A . 0.9602 ?
C6 C7 . 1.483(3) ?
C9 C10 . 1.494(4) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9597 ?
C10 H10A . 0.9599 ?
C10 H10B . 0.9598 ?
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 . 0.90 1.92 2.631(2) 134 y
C1 H1B O1 . 0.96 2.44 2.762(3) 99 y
N1 H1A O2 4_576 0.90 2.22 3.081(3) 159 y
C5 H5A O2 4.576 0.96 2.41 3.361(4) 171 y
O2 H2B S1 4.575 0.85 2.44 3.206(2) 150 y
C9 H9A S1 . 0.96 2.68 3.091(2) 106 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
C6 C1 C2 C3 0.5(5)
C1 C2 C3 C4 -1.1(6)
C2 C3 C4 C5 1.6(7)
C3 C4 C5 C6 -1.6(7)
C4 C5 C6 C1 1.0(6)
C4 C5 C6 C7 179.1(3)
C2 C1 C6 C5 -0.4(5)
C2 C1 C6 C7 -178.7(3)
C8 N1 C7 O1 3.5(4)
C8 N1 C7 C6 -177.0(2)
C5 C6 C7 O1 177.6(3)
C1 C6 C7 O1 -4.3(4)
C5 C6 C7 N1 -1.9(4)
C1 C6 C7 N1 176.2(2)
C9 N2 C8 N1 -175.31(19)
C9 N2 C8 S1 5.4(3)
C7 N1 C8 N2 -2.4(3)
C7 N1 C8 S1 177.01(18)
C8 N2 C9 C10 91.3(3)
N2 C9 C10 O2 60.4(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1414145
