#------------------------------------------------------------------------------
#$Date: 2021-07-14 07:58:22 +0300 (Wed, 14 Jul 2021) $
#$Revision: 267526 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/38/2243869.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_2243869
loop_
_publ_author_name
'Tan, Ming Yueh'
'Kwong, Huey Chong'
'Crouse, Karen A.'
'Ravoof, Thahira B. S. A.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 1-{(E)-[4-(4-Hydroxyphenyl)butan-2-ylidene]amino}-3-phenylthiourea:
 crystal structure, Hirshfeld surface analysis and computational study
;
_journal_coeditor_code           HB7978
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              788
_journal_page_last               794
_journal_paper_doi               10.1107/S2056989021006666
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C17 H19 N3 O S'
_chemical_formula_moiety         'C17 H19 N3 O S'
_chemical_formula_sum            'C17 H19 N3 O S'
_chemical_formula_weight         313.41
_chemical_name_systematic
;
1-{(E)-[4-(4-Hydroxyphenyl)butan-2-ylidene]amino}-3-phenylthiourea
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                70.578(5)
_cell_angle_beta                 82.671(5)
_cell_angle_gamma                68.723(6)
_cell_formula_units_Z            2
_cell_length_a                   8.0605(6)
_cell_length_b                   9.5635(6)
_cell_length_c                   11.4397(6)
_cell_measurement_reflns_used    7107
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72
_cell_measurement_theta_min      4
_cell_volume                     774.95(9)
_computing_cell_refinement
;
CrysAlisPro (Agilent, 2012)
;
_computing_data_collection
;
CrysAlisPro (Agilent, 2012)
;
_computing_data_reduction
;
CrysAlisPro (Agilent, 2012)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg,
2006)
;
_computing_publication_material
;
PublCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15291
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.870
_diffrn_reflns_theta_min         4.098
_exptl_absorpt_coefficient_mu    1.893
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Agilent, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.213
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2982
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0391
_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)+(0.0658P)²+0.2814P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1085
_reflns_number_gt                2712
_reflns_number_total             2982
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7978sup1.cif
_cod_data_source_block           I
_cod_database_code               2243869
_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   0.557
_shelx_estimated_absorpt_t_max   0.928
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.93080(5) 0.19624(4) 0.46989(4) 0.02796(15) Uani d 1 . .
O O1 0.12066(15) 1.17646(14) 0.21473(11) 0.0292(3) Uani d 1 . .
H H1O 0.082(3) 1.159(3) 0.2882(11) 0.044 Uiso d 1 . .
N N1 0.77812(17) 0.49550(15) 0.48469(12) 0.0233(3) Uani d 1 . .
H H1N 0.774(2) 0.5919(13) 0.4427(16) 0.028 Uiso d 1 . .
N N2 0.95702(17) 0.46117(15) 0.31940(12) 0.0237(3) Uani d 1 . .
H H2N 1.024(2) 0.3997(19) 0.2772(15) 0.028 Uiso d 1 . .
N N3 0.92493(17) 0.62221(15) 0.27822(12) 0.0235(3) Uani d 1 . .
C C1 0.8821(2) 0.39389(18) 0.42601(14) 0.0223(3) Uani d 1 . .
C C2 0.6701(2) 0.47628(18) 0.59294(14) 0.0219(3) Uani d 1 . .
C C3 0.6397(2) 0.33626(18) 0.66028(15) 0.0247(3) Uani d 1 . .
H H3 0.695700 0.243795 0.636170 0.030 Uiso calc 1 . .
C C4 0.5271(2) 0.33353(19) 0.76263(15) 0.0254(3) Uani d 1 . .
H H4 0.506601 0.238203 0.808407 0.030 Uiso calc 1 . .
C C5 0.4437(2) 0.4669(2) 0.79964(15) 0.0268(4) Uani d 1 . .
H H5 0.366970 0.463257 0.870039 0.032 Uiso calc 1 . .
C C6 0.4742(2) 0.6063(2) 0.73207(16) 0.0300(4) Uani d 1 . .
H H6 0.417842 0.698703 0.756202 0.036 Uiso calc 1 . .
C C7 0.5864(2) 0.61034(19) 0.62989(15) 0.0271(4) Uani d 1 . .
H H7 0.606583 0.705860 0.584298 0.033 Uiso calc 1 . .
C C8 0.9943(2) 0.67483(18) 0.17277(15) 0.0241(3) Uani d 1 . .
C C9 1.1028(2) 0.5771(2) 0.09267(16) 0.0323(4) Uani d 1 . .
H H9A 1.224584 0.522396 0.124235 0.048 Uiso calc 1 . .
H H9B 1.104985 0.645704 0.007433 0.048 Uiso calc 1 . .
H H9C 1.049551 0.499250 0.094012 0.048 Uiso calc 1 . .
C C10 0.9738(2) 0.84652(19) 0.12493(15) 0.0265(4) Uani d 1 . .
H H10A 0.909132 0.893089 0.045447 0.032 Uiso calc 1 . .
H H10B 1.094242 0.854018 0.106361 0.032 Uiso calc 1 . .
C C11 0.8784(2) 0.94844(19) 0.20771(15) 0.0269(4) Uani d 1 . .
H H11A 0.922435 0.889481 0.293362 0.032 Uiso calc 1 . .
H H11B 0.911704 1.044499 0.179824 0.032 Uiso calc 1 . .
C C12 0.6776(2) 0.99862(17) 0.21054(15) 0.0234(3) Uani d 1 . .
C C13 0.5843(2) 0.97100(18) 0.32206(15) 0.0254(3) Uani d 1 . .
H H13 0.648932 0.912561 0.396999 0.030 Uiso calc 1 . .
C C14 0.3991(2) 1.02660(18) 0.32684(15) 0.0260(3) Uani d 1 . .
H H14 0.338550 1.005371 0.404055 0.031 Uiso calc 1 . .
C C15 0.3032(2) 1.11362(18) 0.21756(15) 0.0247(3) Uani d 1 . .
C C16 0.3935(2) 1.14113(18) 0.10509(15) 0.0257(3) Uani d 1 . .
H H16 0.328803 1.198894 0.030121 0.031 Uiso calc 1 . .
C C17 0.5781(2) 1.08424(18) 0.10229(15) 0.0253(3) Uani d 1 . .
H H17 0.638311 1.103991 0.024812 0.030 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C15 O1 H1O . . 108.4(15) ?
C1 N1 C2 . . 132.42(13) ?
C1 N1 H1N . . 110.3(13) ?
C2 N1 H1N . . 117.2(13) ?
C1 N2 N3 . . 120.90(13) ?
C1 N2 H2N . . 117.6(13) ?
N3 N2 H2N . . 121.4(13) ?
C8 N3 N2 . . 115.76(14) ?
N1 C1 N2 . . 114.40(13) ?
N1 C1 S1 . . 128.00(12) ?
N2 C1 S1 . . 117.60(12) ?
C7 C2 C3 . . 119.28(15) ?
C7 C2 N1 . . 115.94(13) ?
C3 C2 N1 . . 124.75(15) ?
C4 C3 C2 . . 119.36(15) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
C3 C4 C5 . . 121.43(14) ?
C3 C4 H4 . . 119.3 ?
C5 C4 H4 . . 119.3 ?
C4 C5 C6 . . 119.00(15) ?
C4 C5 H5 . . 120.5 ?
C6 C5 H5 . . 120.5 ?
C7 C6 C5 . . 120.06(16) ?
C7 C6 H6 . . 120.0 ?
C5 C6 H6 . . 120.0 ?
C6 C7 C2 . . 120.87(15) ?
C6 C7 H7 . . 119.6 ?
C2 C7 H7 . . 119.6 ?
N3 C8 C9 . . 125.38(14) ?
N3 C8 C10 . . 118.97(15) ?
C9 C8 C10 . . 115.60(14) ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C8 C10 C11 . . 117.78(14) ?
C8 C10 H10A . . 107.9 ?
C11 C10 H10A . . 107.9 ?
C8 C10 H10B . . 107.9 ?
C11 C10 H10B . . 107.9 ?
H10A C10 H10B . . 107.2 ?
C12 C11 C10 . . 115.73(13) ?
C12 C11 H11A . . 108.3 ?
C10 C11 H11A . . 108.3 ?
C12 C11 H11B . . 108.3 ?
C10 C11 H11B . . 108.3 ?
H11A C11 H11B . . 107.4 ?
C13 C12 C17 . . 117.43(15) ?
C13 C12 C11 . . 121.19(14) ?
C17 C12 C11 . . 121.22(14) ?
C14 C13 C12 . . 121.84(15) ?
C14 C13 H13 . . 119.1 ?
C12 C13 H13 . . 119.1 ?
C13 C14 C15 . . 119.51(15) ?
C13 C14 H14 . . 120.2 ?
C15 C14 H14 . . 120.2 ?
O1 C15 C16 . . 117.28(14) ?
O1 C15 C14 . . 123.09(15) ?
C16 C15 C14 . . 119.62(15) ?
C17 C16 C15 . . 119.96(15) ?
C17 C16 H16 . . 120.0 ?
C15 C16 H16 . . 120.0 ?
C16 C17 C12 . . 121.62(15) ?
C16 C17 H17 . . 119.2 ?
C12 C17 H17 . . 119.2 ?
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 . 1.6910(15) ?
O1 C15 . 1.373(2) ?
O1 H1O . 0.842(10) ?
N1 C1 . 1.340(2) ?
N1 C2 . 1.419(2) ?
N1 H1N . 0.877(9) ?
N2 C1 . 1.356(2) ?
N2 N3 . 1.3857(18) ?
N2 H2N . 0.874(9) ?
N3 C8 . 1.284(2) ?
C2 C7 . 1.392(2) ?
C2 C3 . 1.397(2) ?
C3 C4 . 1.386(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.387(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.392(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.382(2) ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 C9 . 1.500(2) ?
C8 C10 . 1.501(2) ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 C11 . 1.524(2) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.512(2) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.392(2) ?
C12 C17 . 1.396(2) ?
C13 C14 . 1.392(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.393(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.389(2) ?
C16 C17 . 1.387(2) ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
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
N1 H1N N3 . 0.877(15) 2.101(17) 2.6214(19) 117.3(12)
O1 H1O S1 1_465 0.842(14) 2.337(18) 3.1489(13) 162(2)
N2 H2N O1 1_645 0.873(17) 2.311(18) 3.1219(19) 154.5(15)
C11 H11A S1 2_766 0.99 2.84 3.7936(17) 163
C11 H11B O1 1_655 0.99 2.58 3.438(2) 145
C9 H9A Cg1 2_766 0.98 2.90 3.6862(19) 138
C4 H4 Cg2 2_666 0.95 2.90 3.6939(19) 142
C6 H6 Cg2 2_676 0.98 2.84 3.601(2) 138
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
C1 N2 N3 C8 . . . . -176.20(13) ?
C2 N1 C1 N2 . . . . 176.34(14) ?
C2 N1 C1 S1 . . . . -4.5(2) ?
N3 N2 C1 N1 . . . . 0.0(2) ?
N3 N2 C1 S1 . . . . -179.27(11) ?
C1 N1 C2 C7 . . . . 176.90(15) ?
C1 N1 C2 C3 . . . . -5.1(3) ?
C7 C2 C3 C4 . . . . -0.1(2) ?
N1 C2 C3 C4 . . . . -178.09(14) ?
C2 C3 C4 C5 . . . . 0.1(2) ?
C3 C4 C5 C6 . . . . 0.1(2) ?
C4 C5 C6 C7 . . . . -0.1(2) ?
C5 C6 C7 C2 . . . . 0.0(3) ?
C3 C2 C7 C6 . . . . 0.1(2) ?
N1 C2 C7 C6 . . . . 178.22(14) ?
N2 N3 C8 C9 . . . . 0.7(2) ?
N2 N3 C8 C10 . . . . -176.77(12) ?
N3 C8 C10 C11 . . . . 2.8(2) ?
C9 C8 C10 C11 . . . . -174.92(13) ?
C8 C10 C11 C12 . . . . -78.12(18) ?
C10 C11 C12 C13 . . . . 126.58(16) ?
C10 C11 C12 C17 . . . . -58.04(19) ?
C17 C12 C13 C14 . . . . -0.3(2) ?
C11 C12 C13 C14 . . . . 175.22(14) ?
C12 C13 C14 C15 . . . . -0.6(2) ?
C13 C14 C15 O1 . . . . -178.06(14) ?
C13 C14 C15 C16 . . . . 1.3(2) ?
O1 C15 C16 C17 . . . . 178.31(13) ?
C14 C15 C16 C17 . . . . -1.0(2) ?
C15 C16 C17 C12 . . . . 0.1(2) ?
C13 C12 C17 C16 . . . . 0.5(2) ?
C11 C12 C17 C16 . . . . -175.00(14) ?

_cod_database_fobs_code 2243869
