#------------------------------------------------------------------------------
#$Date: 2022-01-15 04:37:19 +0200 (Sat, 15 Jan 2022) $
#$Revision: 272053 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/40/2244011.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_2244011
loop_
_publ_author_name
'Dhaene, Evert'
'Van Driessche, Isabel'
'De Buysser, Klaartje'
'Van Hecke, Kristof'
_publ_section_title
;
 Crystal structures of three N,N,N'-trisubstituted
 thioureas for reactivity-controlled nanocrystal synthesis
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022000147
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C22 H22 N2 S'
_chemical_formula_moiety         'C22 H22 N2 S'
_chemical_formula_sum            'C22 H22 N2 S'
_chemical_formula_weight         346.48
_chemical_name_systematic
;
N,N,N'-Tribenzylthiourea
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.042(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2378(4)
_cell_length_b                   14.7792(5)
_cell_length_c                   11.3165(5)
_cell_measurement_reflns_used    8187
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      73.9640
_cell_measurement_theta_min      3.9950
_cell_volume                     1838.15(12)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2019)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2019)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2019)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
Mercury (Macrae et al.,  2020)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b\)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015a\)
;
_diffrn_ambient_temperature      100.0(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16515
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.154
_diffrn_reflns_theta_min         4.022
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.590
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.750
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2019)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.309
_refine_ls_abs_structure_details -
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3589
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0430
_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)+(0.0753P)²+0.4416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1230
_reflns_number_gt                3256
_reflns_number_total             3589
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vm2258sup1.cif
_cod_data_source_block           1
_cod_database_code               2244011
_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.
;
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'
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 0.10482(3) 0.29165(3) 0.32245(3) 0.02217(14) Uani d 1 . .
N N1 0.12474(11) 0.23113(8) 0.54565(11) 0.0198(3) Uani d 1 . .
N N2 0.25536(10) 0.34685(8) 0.52442(11) 0.0191(3) Uani d 1 . .
C C1 0.16633(12) 0.28879(9) 0.47205(13) 0.0177(3) Uani d 1 . .
C C2 0.04085(13) 0.15697(10) 0.50233(13) 0.0209(3) Uani d 1 . .
H H2A -0.024231 0.179223 0.435803 0.025 Uiso calc 1 . .
H H2B 0.002213 0.136546 0.568717 0.025 Uiso calc 1 . .
C C3 0.10428(12) 0.07750(10) 0.45767(14) 0.0215(3) Uani d 1 . .
C C4 0.20059(15) 0.03591(12) 0.53478(18) 0.0358(4) Uani d 1 . .
H H4 0.226181 0.057328 0.615227 0.043 Uiso calc 1 . .
C C5 0.25996(16) -0.03682(13) 0.4954(2) 0.0519(6) Uani d 1 . .
H H5 0.326738 -0.064616 0.548228 0.062 Uiso calc 1 . .
H H1 0.154(3) 0.2304(18) 0.622(3) 0.062 Uiso d 1 . .
C C6 0.22149(18) -0.06872(13) 0.3786(2) 0.0494(6) Uani d 1 . .
H H6 0.262381 -0.118215 0.351143 0.059 Uiso calc 1 . .
C C7 0.1240(2) -0.02889(12) 0.30214(19) 0.0433(5) Uani d 1 . .
H H7 0.096928 -0.051638 0.222546 0.052 Uiso calc 1 . .
C C8 0.06532(16) 0.04457(11) 0.34141(15) 0.0299(4) Uani d 1 . .
H H8 -0.001553 0.072197 0.288476 0.036 Uiso calc 1 . .
C C9 0.31744(12) 0.40391(10) 0.45137(13) 0.0202(3) Uani d 1 . .
H H9A 0.313944 0.374034 0.372425 0.024 Uiso calc 1 . .
H H9B 0.404170 0.408858 0.492068 0.024 Uiso calc 1 . .
C C10 0.26494(12) 0.49838(10) 0.42917(13) 0.0190(3) Uani d 1 . .
C C11 0.31752(13) 0.55802(10) 0.35960(14) 0.0242(3) Uani d 1 . .
H H11 0.384844 0.538845 0.327235 0.029 Uiso calc 1 . .
C C12 0.27248(15) 0.64526(11) 0.33705(15) 0.0281(4) Uani d 1 . .
H H12 0.308310 0.685134 0.288571 0.034 Uiso calc 1 . .
C C13 0.17537(14) 0.67414(11) 0.38522(15) 0.0276(4) Uani d 1 . .
H H13 0.144508 0.733810 0.370034 0.033 Uiso calc 1 . .
C C14 0.12353(13) 0.61561(10) 0.45559(15) 0.0249(3) Uani d 1 . .
H H14 0.057692 0.635536 0.489717 0.030 Uiso calc 1 . .
C C15 0.16720(12) 0.52792(10) 0.47662(13) 0.0211(3) Uani d 1 . .
H H15 0.130022 0.487852 0.523739 0.025 Uiso calc 1 . .
C C16 0.29405(13) 0.35662(10) 0.65564(13) 0.0209(3) Uani d 1 . .
H H16A 0.222424 0.347522 0.692503 0.025 Uiso calc 1 . .
H H16B 0.323109 0.419334 0.673830 0.025 Uiso calc 1 . .
C C17 0.39376(12) 0.29173(10) 0.71478(14) 0.0195(3) Uani d 1 . .
C C18 0.45690(13) 0.31034(11) 0.83213(14) 0.0230(3) Uani d 1 . .
H H18 0.438430 0.363493 0.871962 0.028 Uiso calc 1 . .
C C19 0.54635(13) 0.25185(11) 0.89097(14) 0.0264(3) Uani d 1 . .
H H19 0.589405 0.265389 0.970497 0.032 Uiso calc 1 . .
C C20 0.57320(13) 0.17348(11) 0.83395(15) 0.0263(3) Uani d 1 . .
H H20 0.634493 0.133350 0.874170 0.032 Uiso calc 1 . .
C C21 0.50997(13) 0.15434(11) 0.71817(15) 0.0244(3) Uani d 1 . .
H H21 0.527282 0.100429 0.679235 0.029 Uiso calc 1 . .
C C22 0.42111(13) 0.21354(10) 0.65824(14) 0.0221(3) Uani d 1 . .
H H22 0.379057 0.200265 0.578260 0.027 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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -10 0 0.0839
-2 3 7 0.0686
2 -2 -7 0.1305
2 6 -5 0.0865
-2 -6 5 0.0865
-7 0 0 0.0553
7 0 0 0.0010
1 9 1 0.0994
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
C1 N1 C2 . . 123.48(12) ?
C1 N1 H1 . . 121.3(18) ?
C2 N1 H1 . . 114.6(18) ?
C1 N2 C9 . . 121.00(12) ?
C1 N2 C16 . . 122.75(13) ?
C9 N2 C16 . . 116.25(11) ?
N1 C1 S1 . . 120.99(11) ?
N1 C1 N2 . . 116.81(13) ?
N2 C1 S1 . . 122.13(11) ?
N1 C2 H2A . . 109.2 ?
N1 C2 H2B . . 109.2 ?
N1 C2 C3 . . 112.20(11) ?
H2A C2 H2B . . 107.9 ?
C3 C2 H2A . . 109.2 ?
C3 C2 H2B . . 109.2 ?
C4 C3 C2 . . 119.63(14) ?
C4 C3 C8 . . 119.56(15) ?
C8 C3 C2 . . 120.79(14) ?
C3 C4 H4 . . 119.8 ?
C3 C4 C5 . . 120.44(18) ?
C5 C4 H4 . . 119.8 ?
C4 C5 H5 . . 120.1 ?
C6 C5 C4 . . 119.70(19) ?
C6 C5 H5 . . 120.1 ?
C5 C6 H6 . . 119.9 ?
C7 C6 C5 . . 120.19(17) ?
C7 C6 H6 . . 119.9 ?
C6 C7 H7 . . 120.0 ?
C6 C7 C8 . . 120.03(18) ?
C8 C7 H7 . . 120.0 ?
C3 C8 C7 . . 120.05(17) ?
C3 C8 H8 . . 120.0 ?
C7 C8 H8 . . 120.0 ?
N2 C9 H9A . . 108.7 ?
N2 C9 H9B . . 108.7 ?
N2 C9 C10 . . 114.29(12) ?
H9A C9 H9B . . 107.6 ?
C10 C9 H9A . . 108.7 ?
C10 C9 H9B . . 108.7 ?
C11 C10 C9 . . 118.69(13) ?
C15 C10 C9 . . 122.46(13) ?
C15 C10 C11 . . 118.84(14) ?
C10 C11 H11 . . 119.7 ?
C12 C11 C10 . . 120.66(15) ?
C12 C11 H11 . . 119.7 ?
C11 C12 H12 . . 120.0 ?
C13 C12 C11 . . 120.03(15) ?
C13 C12 H12 . . 120.0 ?
C12 C13 H13 . . 120.2 ?
C14 C13 C12 . . 119.64(14) ?
C14 C13 H13 . . 120.2 ?
C13 C14 H14 . . 119.8 ?
C13 C14 C15 . . 120.39(15) ?
C15 C14 H14 . . 119.8 ?
C10 C15 H15 . . 119.8 ?
C14 C15 C10 . . 120.43(14) ?
C14 C15 H15 . . 119.8 ?
N2 C16 H16A . . 108.6 ?
N2 C16 H16B . . 108.6 ?
N2 C16 C17 . . 114.82(12) ?
H16A C16 H16B . . 107.5 ?
C17 C16 H16A . . 108.6 ?
C17 C16 H16B . . 108.6 ?
C18 C17 C16 . . 118.44(13) ?
C22 C17 C16 . . 122.47(13) ?
C22 C17 C18 . . 119.05(14) ?
C17 C18 H18 . . 119.7 ?
C19 C18 C17 . . 120.51(15) ?
C19 C18 H18 . . 119.7 ?
C18 C19 H19 . . 119.9 ?
C18 C19 C20 . . 120.19(14) ?
C20 C19 H19 . . 119.9 ?
C19 C20 H20 . . 120.3 ?
C21 C20 C19 . . 119.47(14) ?
C21 C20 H20 . . 120.3 ?
C20 C21 H21 . . 119.8 ?
C20 C21 C22 . . 120.48(15) ?
C22 C21 H21 . . 119.8 ?
C17 C22 C21 . . 120.29(14) ?
C17 C22 H22 . . 119.9 ?
C21 C22 H22 . . 119.9 ?
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 . 1.6905(14) ?
N1 C1 . 1.3419(19) ?
N1 C2 . 1.4621(18) ?
N1 H1 . 0.85(3) ?
N2 C1 . 1.3569(18) ?
N2 C9 . 1.4566(19) ?
N2 C16 . 1.4648(19) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C2 C3 . 1.514(2) ?
C3 C4 . 1.384(2) ?
C3 C8 . 1.385(2) ?
C4 H4 . 0.9500 ?
C4 C5 . 1.387(3) ?
C5 H5 . 0.9500 ?
C5 C6 . 1.384(3) ?
C6 H6 . 0.9500 ?
C6 C7 . 1.378(3) ?
C7 H7 . 0.9500 ?
C7 C8 . 1.391(3) ?
C8 H8 . 0.9500 ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C9 C10 . 1.5162(19) ?
C10 C11 . 1.393(2) ?
C10 C15 . 1.390(2) ?
C11 H11 . 0.9500 ?
C11 C12 . 1.389(2) ?
C12 H12 . 0.9500 ?
C12 C13 . 1.385(3) ?
C13 H13 . 0.9500 ?
C13 C14 . 1.384(2) ?
C14 H14 . 0.9500 ?
C14 C15 . 1.389(2) ?
C15 H15 . 0.9500 ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C16 C17 . 1.5199(19) ?
C17 C18 . 1.396(2) ?
C17 C22 . 1.386(2) ?
C18 H18 . 0.9500 ?
C18 C19 . 1.386(2) ?
C19 H19 . 0.9500 ?
C19 C20 . 1.389(2) ?
C20 H20 . 0.9500 ?
C20 C21 . 1.383(2) ?
C21 H21 . 0.9500 ?
C21 C22 . 1.393(2) ?
C22 H22 . 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_D
_geom_hbond_site_symmetry_H
_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 1_555 1_555 4_566 0.86(3) 2.47(3) 3.2044(13) 145(3) 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
N1 C2 C3 C4 . . . . 57.70(19) ?
N1 C2 C3 C8 . . . . -123.79(15) ?
N2 C9 C10 C11 . . . . -179.60(12) ?
N2 C9 C10 C15 . . . . 1.06(19) ?
N2 C16 C17 C18 . . . . 164.26(13) ?
N2 C16 C17 C22 . . . . -18.1(2) ?
C1 N1 C2 C3 . . . . 77.11(17) ?
C1 N2 C9 C10 . . . . 95.30(15) ?
C1 N2 C16 C17 . . . . 88.11(17) ?
C2 N1 C1 S1 . . . . 11.18(19) ?
C2 N1 C1 N2 . . . . -171.82(12) ?
C2 C3 C4 C5 . . . . -179.84(17) ?
C2 C3 C8 C7 . . . . -179.52(15) ?
C3 C4 C5 C6 . . . . -0.9(3) ?
C4 C3 C8 C7 . . . . -1.0(2) ?
C4 C5 C6 C7 . . . . -0.5(3) ?
C5 C6 C7 C8 . . . . 1.1(3) ?
C6 C7 C8 C3 . . . . -0.4(3) ?
C8 C3 C4 C5 . . . . 1.6(3) ?
C9 N2 C1 S1 . . . . -11.01(18) ?
C9 N2 C1 N1 . . . . 172.03(12) ?
C9 N2 C16 C17 . . . . -92.33(15) ?
C9 C10 C11 C12 . . . . -179.93(13) ?
C9 C10 C15 C14 . . . . 178.87(13) ?
C10 C11 C12 C13 . . . . 0.9(2) ?
C11 C10 C15 C14 . . . . -0.5(2) ?
C11 C12 C13 C14 . . . . -0.1(2) ?
C12 C13 C14 C15 . . . . -0.9(2) ?
C13 C14 C15 C10 . . . . 1.2(2) ?
C15 C10 C11 C12 . . . . -0.6(2) ?
C16 N2 C1 S1 . . . . 168.53(10) ?
C16 N2 C1 N1 . . . . -8.43(19) ?
C16 N2 C9 C10 . . . . -84.26(14) ?
C16 C17 C18 C19 . . . . 178.27(14) ?
C16 C17 C22 C21 . . . . -177.37(14) ?
C17 C18 C19 C20 . . . . -0.6(2) ?
C18 C17 C22 C21 . . . . 0.3(2) ?
C18 C19 C20 C21 . . . . 0.0(2) ?
C19 C20 C21 C22 . . . . 0.8(2) ?
C20 C21 C22 C17 . . . . -1.0(2) ?
C22 C17 C18 C19 . . . . 0.5(2) ?

_cod_database_fobs_code 2244011
