##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic     
;
3,3-Bis(2-hydroxyethyl)-1-(4-methylbenzoyl)thiourea
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H18 N2 O3 S1'
_chemical_formula_sum     'C13 H18 N2 O3 S1'
_chemical_formula_weight     282.35
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     7.4051(10)
_cell_length_b     10.6213(15)
_cell_length_c     18.569(3)
_cell_angle_alpha     90
_cell_angle_beta     94.117(2)
_cell_angle_gamma     90
_cell_volume     1456.7(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2509
_cell_measurement_theta_min     2.20
_cell_measurement_theta_max     22.93
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.120
_exptl_crystal_size_mid     0.090
_exptl_crystal_size_min     0.080
_exptl_crystal_density_diffrn     1.287
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     600
_exptl_absorpt_coefficient_mu     0.228
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_absorpt_correction_T_min     0.6546
_exptl_absorpt_correction_T_max     0.7456
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX diffractometer'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     18125
_diffrn_reflns_av_R_equivalents     0.0505
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_theta_min     2.199
_diffrn_reflns_theta_max     27.498
_diffrn_reflns_theta_full     27.498
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     24
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details     ?
_reflns_number_total     3339
_reflns_number_gt     2263
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0674
_refine_ls_R_factor_gt     0.0390
_refine_ls_wR_factor_gt     0.0850
_refine_ls_wR_factor_ref     0.0984
_refine_ls_goodness_of_fit_ref     1.035
_refine_ls_restrained_S_all     1.034
_refine_ls_number_reflns     3339
_refine_ls_number_parameters     182
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0374P)²+0.2262P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.172
_refine_diff_density_min     -0.202
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
    'S' 'S' 0.1246 0.1234
                         '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'
_computing_data_collection
;
SMART (Bruker, 2008)
;
_computing_cell_refinement
;
SMART (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014/7 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg,
2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.32019(6) 0.58997(5) 0.40517(3) 0.05150(16) Uani d 1 . .
    O O1 0.20850(18) 0.31841(13) 0.20234(8) 0.0600(4) Uani d 1 . .
    H H1O 0.239(3) 0.2473(13) 0.1888(13) 0.090 Uiso d 1 . .
    O O2 -0.27874(16) 0.58125(13) 0.35097(7) 0.0534(4) Uani d 1 . .
    H H2O -0.3778(19) 0.585(2) 0.3699(11) 0.080 Uiso d 1 . .
    O O3 0.37968(18) 0.75187(12) 0.26514(8) 0.0602(4) Uani d 1 . .
    N N1 0.06795(17) 0.47500(13) 0.31953(7) 0.0382(3) Uani d 1 . .
    N N2 0.31599(19) 0.54248(13) 0.26306(8) 0.0402(3) Uani d 1 . .
    H H2N 0.304(2) 0.4767(12) 0.2356(8) 0.048 Uiso d 1 . .
    C C1 0.2270(2) 0.53452(15) 0.32668(9) 0.0380(4) Uani d 1 . .
    C C2 -0.0239(2) 0.44158(17) 0.24885(10) 0.0448(4) Uani d 1 . .
    H H2A 0.0053 0.5045 0.2137 0.054 Uiso calc 1 . .
    H H2B -0.1537 0.4438 0.2528 0.054 Uiso calc 1 . .
    C C3 0.0273(2) 0.31392(18) 0.22177(11) 0.0524(5) Uani d 1 . .
    H H3A 0.0155 0.2513 0.2592 0.063 Uiso calc 1 . .
    H H3B -0.0526 0.2907 0.1802 0.063 Uiso calc 1 . .
    C C4 -0.0291(2) 0.44025(17) 0.38245(10) 0.0456(4) Uani d 1 . .
    H H4A 0.0583 0.4179 0.4218 0.055 Uiso calc 1 . .
    H H4B -0.1024 0.3664 0.3707 0.055 Uiso calc 1 . .
    C C5 -0.1497(2) 0.54346(19) 0.40748(10) 0.0497(5) Uani d 1 . .
    H H5A -0.2125 0.5138 0.4483 0.060 Uiso calc 1 . .
    H H5B -0.0762 0.6153 0.4232 0.060 Uiso calc 1 . .
    C C6 0.3952(2) 0.64952(16) 0.23710(9) 0.0405(4) Uani d 1 . .
    C C7 0.4941(2) 0.63211(16) 0.17111(9) 0.0393(4) Uani d 1 . .
    C C8 0.5608(2) 0.51755(17) 0.14953(9) 0.0449(4) Uani d 1 . .
    H H8 0.5419 0.4455 0.1764 0.054 Uiso calc 1 . .
    C C9 0.6557(3) 0.5097(2) 0.08809(10) 0.0562(5) Uani d 1 . .
    H H9 0.7011 0.4322 0.0747 0.067 Uiso calc 1 . .
    C C10 0.6843(3) 0.6145(2) 0.04626(10) 0.0584(5) Uani d 1 . .
    C C11 0.6157(3) 0.7282(2) 0.06798(11) 0.0631(6) Uani d 1 . .
    H H11 0.6320 0.7999 0.0404 0.076 Uiso calc 1 . .
    C C12 0.5241(3) 0.73742(18) 0.12945(11) 0.0557(5) Uani d 1 . .
    H H12 0.4815 0.8154 0.1434 0.067 Uiso calc 1 . .
    C C13 0.7870(4) 0.6055(3) -0.02119(12) 0.0919(9) Uani d 1 . .
    H H13A 0.7224 0.6506 -0.0598 0.138 Uiso calc 1 . .
    H H13B 0.7983 0.5187 -0.0346 0.138 Uiso calc 1 . .
    H H13C 0.9052 0.6416 -0.0120 0.138 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C1 . 1.6744(17) ?
    O1 C3 . 1.415(2) ?
    O1 H1O . 0.832(9) ?
    O2 C5 . 1.425(2) ?
    O2 H2O . 0.836(9) ?
    O3 C6 . 1.214(2) ?
    N1 C1 . 1.335(2) ?
    N1 C4 . 1.462(2) ?
    N1 C2 . 1.477(2) ?
    N2 C6 . 1.382(2) ?
    N2 C1 . 1.396(2) ?
    N2 H2N . 0.866(9) ?
    C2 C3 . 1.504(2) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 C5 . 1.508(3) ?
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 C7 . 1.483(2) ?
    C7 C8 . 1.383(2) ?
    C7 C12 . 1.387(2) ?
    C8 C9 . 1.384(2) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.382(3) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.382(3) ?
    C10 C13 . 1.514(3) ?
    C11 C12 . 1.373(3) ?
    C11 H11 . 0.9300 ?
    C12 H12 . 0.9300 ?
    C13 H13A . 0.9600 ?
    C13 H13B . 0.9600 ?
    C13 H13C . 0.9600 ?
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
    C3 O1 H1O . . 109.1(18) ?
    C5 O2 H2O . . 105.3(16) ?
    C1 N1 C4 . . 121.39(14) ?
    C1 N1 C2 . . 123.27(14) ?
    C4 N1 C2 . . 115.33(13) ?
    C6 N2 C1 . . 125.67(14) ?
    C6 N2 H2N . . 119.0(12) ?
    C1 N2 H2N . . 114.6(12) ?
    N1 C1 N2 . . 114.30(14) ?
    N1 C1 S1 . . 123.97(13) ?
    N2 C1 S1 . . 121.67(12) ?
    N1 C2 C3 . . 113.76(15) ?
    N1 C2 H2A . . 108.8 ?
    C3 C2 H2A . . 108.8 ?
    N1 C2 H2B . . 108.8 ?
    C3 C2 H2B . . 108.8 ?
    H2A C2 H2B . . 107.7 ?
    O1 C3 C2 . . 108.71(15) ?
    O1 C3 H3A . . 109.9 ?
    C2 C3 H3A . . 109.9 ?
    O1 C3 H3B . . 109.9 ?
    C2 C3 H3B . . 109.9 ?
    H3A C3 H3B . . 108.3 ?
    N1 C4 C5 . . 113.48(14) ?
    N1 C4 H4A . . 108.9 ?
    C5 C4 H4A . . 108.9 ?
    N1 C4 H4B . . 108.9 ?
    C5 C4 H4B . . 108.9 ?
    H4A C4 H4B . . 107.7 ?
    O2 C5 C4 . . 111.00(15) ?
    O2 C5 H5A . . 109.4 ?
    C4 C5 H5A . . 109.4 ?
    O2 C5 H5B . . 109.4 ?
    C4 C5 H5B . . 109.4 ?
    H5A C5 H5B . . 108.0 ?
    O3 C6 N2 . . 122.09(17) ?
    O3 C6 C7 . . 122.23(16) ?
    N2 C6 C7 . . 115.64(15) ?
    C8 C7 C12 . . 118.21(17) ?
    C8 C7 C6 . . 123.83(16) ?
    C12 C7 C6 . . 117.95(16) ?
    C7 C8 C9 . . 120.32(17) ?
    C7 C8 H8 . . 119.8 ?
    C9 C8 H8 . . 119.8 ?
    C10 C9 C8 . . 121.45(19) ?
    C10 C9 H9 . . 119.3 ?
    C8 C9 H9 . . 119.3 ?
    C11 C10 C9 . . 117.76(18) ?
    C11 C10 C13 . . 120.9(2) ?
    C9 C10 C13 . . 121.4(2) ?
    C12 C11 C10 . . 121.24(19) ?
    C12 C11 H11 . . 119.4 ?
    C10 C11 H11 . . 119.4 ?
    C11 C12 C7 . . 121.01(19) ?
    C11 C12 H12 . . 119.5 ?
    C7 C12 H12 . . 119.5 ?
    C10 C13 H13A . . 109.5 ?
    C10 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C10 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
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
    C4 N1 C1 N2 . . . . 169.93(14) ?
    C2 N1 C1 N2 . . . . -11.1(2) ?
    C4 N1 C1 S1 . . . . -7.3(2) ?
    C2 N1 C1 S1 . . . . 171.63(12) ?
    C6 N2 C1 N1 . . . . 133.37(17) ?
    C6 N2 C1 S1 . . . . -49.3(2) ?
    C1 N1 C2 C3 . . . . 89.8(2) ?
    C4 N1 C2 C3 . . . . -91.18(18) ?
    N1 C2 C3 O1 . . . . -70.1(2) ?
    C1 N1 C4 C5 . . . . 86.72(19) ?
    C2 N1 C4 C5 . . . . -92.28(18) ?
    N1 C4 C5 O2 . . . . 57.5(2) ?
    C1 N2 C6 O3 . . . . -6.8(3) ?
    C1 N2 C6 C7 . . . . 175.48(15) ?
    O3 C6 C7 C8 . . . . 160.25(17) ?
    N2 C6 C7 C8 . . . . -22.1(2) ?
    O3 C6 C7 C12 . . . . -18.5(3) ?
    N2 C6 C7 C12 . . . . 159.18(16) ?
    C12 C7 C8 C9 . . . . 0.3(3) ?
    C6 C7 C8 C9 . . . . -178.41(16) ?
    C7 C8 C9 C10 . . . . -0.9(3) ?
    C8 C9 C10 C11 . . . . 0.4(3) ?
    C8 C9 C10 C13 . . . . -179.6(2) ?
    C9 C10 C11 C12 . . . . 0.7(3) ?
    C13 C10 C11 C12 . . . . -179.3(2) ?
    C10 C11 C12 C7 . . . . -1.3(3) ?
    C8 C7 C12 C11 . . . . 0.7(3) ?
    C6 C7 C12 C11 . . . . 179.56(18) ?
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
    N2 H2N O1 . 0.866(13) 1.909(13) 2.728(2) 157.1(14)
    O1 H1O O2 2_545 0.832(16) 1.943(16) 2.769(2) 172(2)
    O2 H2O S1 1_455 0.837(16) 2.376(15) 3.2049(14) 171.1(19)
    C8 H8 O3 2_645 0.93 2.38 3.251(2) 156
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     0.973
_shelx_estimated_absorpt_T_max     0.982
data_global
_journal_date_recd_electronic     2019-09-09
_journal_date_accepted     2019-09-09
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2019
_journal_volume     75
_journal_issue     10
_journal_page_first     1472
_journal_page_last     1478
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989019012581
_journal_coeditor_code     HB7854
loop_
    _publ_contact_author_name
    _publ_contact_author_address
    _publ_contact_author_email
    'Edward R.T. Tiekink'
;
School of Science and Technology,
Sunway University,
No. 5 Jalan Universiti,
47500 Bandar Sunway,
Selangor Darul Ehsan, Malaysia
;
 edwardt@sunway.edu.my
_publ_contact_author_fax     ' +60 3 7491 8633 '
_publ_contact_author_phone     ' +60 3 7491 7173 '
_publ_section_title
;
3,3-Bis(2-hydroxyethyl)-1-(4-methylbenzoyl)thiourea: crystal structure,
Hirshfeld surface analysis and computational study
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    ' Sang Loon Tan ' .
;
Research Centre for Crystalline Materials,
School of Science and Technology,
Sunway University, 47500 Bandar Sunway,
Selangor Darul Ehsan, Malaysia
;
    ' Ainnul Hamidah Syahadah Azizan ' .
;
Research Centre for Crystalline Materials,
School of Science and Technology,
Sunway University, 47500 Bandar Sunway,
Selangor Darul Ehsan, Malaysia
;
    ' Jotani, Mukesh M. ' .
;
Department of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad,
Gujarat 380001, India
;
    'Tiekink, Edward R. T.' .
;
Research Centre for Crystalline Materials,
School of Science and Technology,
Sunway University, 47500 Bandar Sunway,
Selangor Darul Ehsan, Malaysia
;
_publ_section_synopsis
;
The title tri-substituted thiourea derivative is twisted with a dihedral angle
of 72.12 (9)° between the planes through the CN₂S atoms and the 4-tolyl
ring; an intramolecular N--H...O hydrogen bond leads to an S(7) loop.
In the crystal. hydroxyl-O---H...O(hydroxyl) and hydroxyl-O---H...S(thione)
hydrogen bonds give rise to a supramolecular layer in the ab plane.
;
