#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/80/2228036.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228036
loop_
_publ_author_name
'Choi, Hyeong'
'Shim, Yong Suk'
'Han, Byung Hee'
'Kang, Sung Kwon'
'Sung, Chang Keun'
_publ_section_title
;
 1-(2-Hydroxyethyl)-3-(3-methoxyphenyl)thiourea
;
_journal_coeditor_code           TK2706
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2487
_journal_page_last               o2488
_journal_paper_doi               10.1107/S1600536810034665
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C10 H14 N2 O2 S'
_chemical_formula_moiety         'C10 H14 N2 O2 S'
_chemical_formula_sum            'C10 H14 N2 O2 S'
_chemical_formula_weight         226.29
_chemical_name_systematic
;
1-(2-Hydroxyethyl)-3-(3-methoxyphenyl)thiourea
;
_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                 102.9200(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9894(3)
_cell_length_b                   8.0759(2)
_cell_length_c                   12.8067(4)
_cell_measurement_reflns_used    4441
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.14
_cell_measurement_theta_min      2.77
_cell_volume                     1107.81(5)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2010)'
_computing_publication_material  'WinGX  (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.97
_diffrn_measured_fraction_theta_max 0.97
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8965
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.356
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2478
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.08
_refine_ls_R_factor_gt           0.038
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0621P)²+0.0837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.107
_reflns_number_gt                2013
_reflns_number_total             2478
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2706.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2228036
_cod_database_fobs_code          2228036
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 0.47197(11) 0.63459(15) 0.77190(10) 0.0330(3) Uani d . 1 . .
C C2 0.46149(11) 0.49103(15) 0.83014(10) 0.0330(3) Uani d . 1 . .
H H2 0.5124 0.4001 0.8268 0.04 Uiso calc R 1 . .
C C3 0.37377(11) 0.48652(16) 0.89296(10) 0.0350(3) Uani d . 1 . .
C C4 0.29844(13) 0.62354(19) 0.89796(13) 0.0463(4) Uani d . 1 . .
H H4 0.2409 0.621 0.9413 0.056 Uiso calc R 1 . .
C C5 0.30915(14) 0.7629(2) 0.83859(14) 0.0532(4) Uani d . 1 . .
H H5 0.2576 0.8534 0.8412 0.064 Uiso calc R 1 . .
C C6 0.39582(13) 0.76975(19) 0.77507(13) 0.0464(4) Uani d . 1 . .
H H6 0.4027 0.864 0.7351 0.056 Uiso calc R 1 . .
N N7 0.55784(11) 0.64047(14) 0.70312(10) 0.0377(3) Uani d . 1 . .
H H7 0.5267(16) 0.658(2) 0.6393(16) 0.051(5) Uiso d . 1 . .
C C8 0.68277(12) 0.62256(14) 0.73143(11) 0.0341(3) Uani d . 1 . .
S S9 0.76633(4) 0.61967(5) 0.63478(3) 0.05057(15) Uani d . 1 . .
N N10 0.73496(11) 0.60801(14) 0.83569(10) 0.0364(3) Uani d . 1 . .
H H10 0.6920(16) 0.6201(17) 0.8796(14) 0.040(4) Uiso d . 1 . .
C C11 0.86769(12) 0.57980(18) 0.87843(13) 0.0426(3) Uani d . 1 . .
H H11A 0.9014 0.5185 0.8262 0.051 Uiso calc R 1 . .
H H11B 0.8782 0.5124 0.9425 0.051 Uiso calc R 1 . .
C C12 0.94037(12) 0.73800(18) 0.90533(12) 0.0443(3) Uani d . 1 . .
H H12A 1.0289 0.7127 0.9243 0.053 Uiso calc R 1 . .
H H12B 0.9253 0.8091 0.8427 0.053 Uiso calc R 1 . .
O O13 0.90658(11) 0.82309(17) 0.99133(9) 0.0553(3) Uani d . 1 . .
H H13 0.865(2) 0.906(3) 0.973(2) 0.092(8) Uiso d . 1 . .
O O14 0.35374(10) 0.35339(12) 0.95322(9) 0.0469(3) Uani d . 1 . .
C C15 0.40934(16) 0.1998(2) 0.93648(14) 0.0546(4) Uani d . 1 . .
H H15A 0.3879 0.1178 0.9836 0.082 Uiso calc R 1 . .
H H15B 0.4984 0.2123 0.9511 0.082 Uiso calc R 1 . .
H H15C 0.3793 0.1655 0.8635 0.082 Uiso calc R 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
C6 C1 C2 . . 121.14(12) ?
C6 C1 N7 . . 118.68(12) ?
C2 C1 N7 . . 120.10(11) ?
C3 C2 C1 . . 118.83(11) ?
C3 C2 H2 . . 120.6 ?
C1 C2 H2 . . 120.6 ?
O14 C3 C2 . . 124.57(12) ?
O14 C3 C4 . . 115.21(12) ?
C2 C3 C4 . . 120.22(13) ?
C5 C4 C3 . . 119.92(14) ?
C5 C4 H4 . . 120 ?
C3 C4 H4 . . 120 ?
C4 C5 C6 . . 120.77(14) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C1 C6 C5 . . 119.10(14) ?
C1 C6 H6 . . 120.5 ?
C5 C6 H6 . . 120.5 ?
C8 N7 C1 . . 127.20(12) ?
C8 N7 H7 . . 117.2(13) ?
C1 N7 H7 . . 115.6(13) ?
N10 C8 N7 . . 117.55(13) ?
N10 C8 S9 . . 123.11(10) ?
N7 C8 S9 . . 119.34(11) ?
C8 N10 C11 . . 124.03(13) ?
C8 N10 H10 . . 119.6(12) ?
C11 N10 H10 . . 116.3(12) ?
N10 C11 C12 . . 112.87(11) ?
N10 C11 H11A . . 109 ?
C12 C11 H11A . . 109 ?
N10 C11 H11B . . 109 ?
C12 C11 H11B . . 109 ?
H11A C11 H11B . . 107.8 ?
O13 C12 C11 . . 111.83(12) ?
O13 C12 H12A . . 109.2 ?
C11 C12 H12A . . 109.2 ?
O13 C12 H12B . . 109.2 ?
C11 C12 H12B . . 109.2 ?
H12A C12 H12B . . 107.9 ?
C12 O13 H13 . . 113.9(18) ?
C3 O14 C15 . . 118.15(11) ?
O14 C15 H15A . . 109.5 ?
O14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
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
C1 C6 . 1.3815(18) ?
C1 C2 . 1.3972(17) ?
C1 N7 . 1.4284(18) ?
C2 C3 . 1.3874(18) ?
C2 H2 . 0.93 ?
C3 O14 . 1.3696(16) ?
C3 C4 . 1.392(2) ?
C4 C5 . 1.378(2) ?
C4 H4 . 0.93 ?
C5 C6 . 1.385(2) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
N7 C8 . 1.3471(17) ?
N7 H7 . 0.824(19) ?
C8 N10 . 1.3353(18) ?
C8 S9 . 1.6983(14) ?
N10 C11 . 1.4567(17) ?
N10 H10 . 0.817(19) ?
C11 C12 . 1.505(2) ?
C11 H11A . 0.97 ?
C11 H11B . 0.97 ?
C12 O13 . 1.4163(19) ?
C12 H12A . 0.97 ?
C12 H12B . 0.97 ?
O13 H13 . 0.81(2) ?
O14 C15 . 1.4200(19) ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
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
N7 H7 O13 4_575 0.824(19) 2.059(19) 2.8619(16) 164.6(17)
N10 H10 O14 3_667 0.817(19) 2.316(19) 3.0877(17) 157.8(15)
O13 H13 S9 2_656 0.81(2) 2.47(2) 3.2532(14) 163(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2081760
