#------------------------------------------------------------------------------
#$Date: 2021-12-03 23:37:28 +0200 (Fri, 03 Dec 2021) $
#$Revision: 271049 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/91/4519183.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_4519183
loop_
_publ_author_name
'Ashfaq, Muhammad'
'Tahir, Muhammad Nawaz'
'Muhammad, Shabbir'
'Munawar, Khurram Shahzad'
'Ali, Akbar'
'Bogdanov, Georgii'
'Alarfaji, Saleh S.'
_publ_section_title
;
 Single-Crystal Investigation, Hirshfeld Surface Analysis, and DFT Study
 of Third-Order NLO Properties of Unsymmetrical Acyl Thiourea Derivatives.
;
_journal_issue                   46
_journal_name_full               'ACS omega'
_journal_page_first              31211
_journal_page_last               31225
_journal_paper_doi               10.1021/acsomega.1c04884
_journal_volume                  6
_journal_year                    2021
_chemical_formula_iupac          'C16 H20 N2 O3 S'
_chemical_formula_moiety         'C16 H20 N2 O3 S'
_chemical_formula_sum            'C16 H20 N2 O3 S'
_chemical_formula_weight         320.40
_chemical_name_systematic
;
4-((3-benzoylthioureido)methyl)cyclohexanecarboxylic acid
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                108.124(10)
_cell_angle_beta                 97.581(10)
_cell_angle_gamma                97.514(7)
_cell_formula_units_Z            2
_cell_length_a                   5.9027(9)
_cell_length_b                   10.2604(16)
_cell_length_c                   14.288(3)
_cell_measurement_reflns_used    1967
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.994
_cell_measurement_theta_min      3.001
_cell_volume                     801.5(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL-2018/3  (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.829
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_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  0.0484
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9207
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.994
_diffrn_reflns_theta_min         3.001
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2790
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0573
_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)+(0.0883P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1765
_reflns_number_gt                1967
_reflns_number_total             3449
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ao1c04884_si_002.cif
_cod_data_source_block           BENZOYLTREN
_cod_original_cell_volume        801.5(2)
_cod_database_code               4519183
_shelx_shelxl_version_number     2018/3
_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, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.46517(12) 0.22128(7) 0.13060(6) 0.0679(3) Uani 1 1 d . . . . .
O1A O 0.2588(6) -0.5401(2) 0.1426(3) 0.0805(14) Uani 0.837(7) 1 d D . P A 1
H1A H 0.376(2) -0.5788(11) 0.150(3) 0.121 Uiso 0.837(7) 1 d D U P A 1
O2A O 0.5685(5) -0.3774(4) 0.2258(3) 0.0754(13) Uani 0.837(7) 1 d D . P A 1
O1B O 0.353(3) -0.5133(14) 0.1013(9) 0.0805(14) Uani 0.163(7) 1 d D . P A 2
H1B H 0.488(6) -0.534(6) 0.113(2) 0.121 Uiso 0.163(7) 1 d D U P A 2
O2B O 0.532(3) -0.384(3) 0.2558(11) 0.0754(13) Uani 0.163(7) 1 d D . P A 2
O3 O 0.2108(3) 0.36728(19) 0.35319(15) 0.0732(6) Uani 1 1 d . . . . .
N1 N -0.0702(4) 0.1684(2) 0.20430(16) 0.0561(6) Uani 1 1 d . . . . .
H1 H 0.062811 0.194850 0.243714 0.067 Uiso 1 1 calc R U . . .
N2 N -0.1304(4) 0.39380(19) 0.27451(16) 0.0511(6) Uani 1 1 d . . . . .
H2A H -0.217574 0.453915 0.271680 0.061 Uiso 1 1 calc R U . . .
C1 C 0.3681(5) -0.4091(3) 0.1859(2) 0.0581(7) Uani 1 1 d D . . . .
C2 C 0.2049(4) -0.3082(2) 0.1807(2) 0.0510(7) Uani 1 1 d . . . . .
H2 H 0.054090 -0.348050 0.191256 0.061 Uiso 1 1 calc R U . . .
C3 C 0.1685(5) -0.2955(3) 0.0767(2) 0.0592(8) Uani 1 1 d . . . . .
H3A H 0.314356 -0.254937 0.064042 0.071 Uiso 1 1 calc R U . . .
H3B H 0.115932 -0.387312 0.026614 0.071 Uiso 1 1 calc R U . . .
C4 C -0.0112(5) -0.2041(2) 0.0690(2) 0.0577(7) Uani 1 1 d . . . . .
H4A H -0.160043 -0.249537 0.075667 0.069 Uiso 1 1 calc R U . . .
H4B H -0.028569 -0.193527 0.003468 0.069 Uiso 1 1 calc R U . . .
C5 C 0.0567(4) -0.0602(2) 0.14946(19) 0.0507(7) Uani 1 1 d . . . . .
H5 H 0.200371 -0.012312 0.138332 0.061 Uiso 1 1 calc R U . . .
C6 C 0.1027(5) -0.0743(3) 0.2522(2) 0.0596(8) Uani 1 1 d . . . . .
H6A H -0.041407 -0.114431 0.266492 0.072 Uiso 1 1 calc R U . . .
H6B H 0.156728 0.017509 0.302032 0.072 Uiso 1 1 calc R U . . .
C7 C 0.2834(5) -0.1659(3) 0.2601(2) 0.0579(7) Uani 1 1 d . . . . .
H7A H 0.431627 -0.122593 0.251313 0.069 Uiso 1 1 calc R U . . .
H7B H 0.303698 -0.175454 0.326017 0.069 Uiso 1 1 calc R U . . .
C8 C -0.1344(5) 0.0233(2) 0.1379(2) 0.0585(7) Uani 1 1 d . . . . .
H8A H -0.166459 0.021096 0.068969 0.070 Uiso 1 1 calc R U . . .
H8B H -0.275389 -0.020019 0.152482 0.070 Uiso 1 1 calc R U . . .
C9 C -0.2071(4) 0.2599(2) 0.20629(19) 0.0478(6) Uani 1 1 d . . . . .
C10 C 0.0686(5) 0.4409(3) 0.3459(2) 0.0529(7) Uani 1 1 d . . . . .
C11 C 0.1054(4) 0.5882(2) 0.41479(18) 0.0484(6) Uani 1 1 d . . . . .
C12 C -0.0593(5) 0.6730(3) 0.4211(2) 0.0611(8) Uani 1 1 d . . . . .
H12 H -0.204435 0.639719 0.379712 0.073 Uiso 1 1 calc R U . . .
C13 C -0.0094(5) 0.8066(3) 0.4886(2) 0.0714(9) Uani 1 1 d . . . . .
H13 H -0.120750 0.863380 0.491534 0.086 Uiso 1 1 calc R U . . .
C14 C 0.2001(6) 0.8569(3) 0.5508(2) 0.0734(9) Uani 1 1 d . . . . .
H14 H 0.232522 0.947611 0.595840 0.088 Uiso 1 1 calc R U . . .
C15 C 0.3615(5) 0.7737(3) 0.5468(3) 0.0823(10) Uani 1 1 d . . . . .
H15 H 0.504043 0.806948 0.590287 0.099 Uiso 1 1 calc R U . . .
C16 C 0.3163(5) 0.6407(3) 0.4791(2) 0.0688(9) Uani 1 1 d . . . . .
H16 H 0.429593 0.585302 0.476598 0.083 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1A H1A 97.2(8) . . ?
C1 O1B H1B 98.6(13) . . ?
C9 N1 C8 122.8(2) . . ?
C9 N1 H1 118.6 . . ?
C8 N1 H1 118.6 . . ?
C10 N2 C9 127.3(2) . . ?
C10 N2 H2A 116.3 . . ?
C9 N2 H2A 116.3 . . ?
O2B C1 O1B 120.7(11) . . ?
O2A C1 O1A 123.3(3) . . ?
O2A C1 C2 125.6(3) . . ?
O2B C1 C2 123.0(12) . . ?
O1B C1 C2 114.9(6) . . ?
O1A C1 C2 111.1(2) . . ?
C7 C2 C1 113.7(2) . . ?
C7 C2 C3 110.6(2) . . ?
C1 C2 C3 110.0(2) . . ?
C7 C2 H2 107.4 . . ?
C1 C2 H2 107.4 . . ?
C3 C2 H2 107.4 . . ?
C4 C3 C2 109.8(2) . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C3 C4 C5 112.1(2) . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C8 113.0(2) . . ?
C6 C5 C4 110.1(2) . . ?
C8 C5 C4 108.7(2) . . ?
C6 C5 H5 108.3 . . ?
C8 C5 H5 108.3 . . ?
C4 C5 H5 108.3 . . ?
C5 C6 C7 112.1(2) . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C2 C7 C6 109.8(2) . . ?
C2 C7 H7A 109.7 . . ?
C6 C7 H7A 109.7 . . ?
C2 C7 H7B 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
N1 C8 C5 112.1(2) . . ?
N1 C8 H8A 109.2 . . ?
C5 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C5 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N1 C9 N2 117.7(2) . . ?
N1 C9 S1 122.66(18) . . ?
N2 C9 S1 119.65(18) . . ?
O3 C10 N2 122.0(2) . . ?
O3 C10 C11 120.8(2) . . ?
N2 C10 C11 117.1(2) . . ?
C16 C11 C12 118.0(2) . . ?
C16 C11 C10 117.3(2) . . ?
C12 C11 C10 124.7(2) . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 119.4(3) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 120.9(3) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C9 1.670(3) . ?
O1A C1 1.325(3) . ?
O1A H1A 0.855(10) . ?
O2A C1 1.199(4) . ?
O1B C1 1.325(8) . ?
O1B H1B 0.859(10) . ?
O2B C1 1.232(9) . ?
O3 C10 1.216(3) . ?
N1 C9 1.313(3) . ?
N1 C8 1.463(3) . ?
N1 H1 0.8600 . ?
N2 C10 1.372(3) . ?
N2 C9 1.389(3) . ?
N2 H2A 0.8600 . ?
C1 C2 1.515(3) . ?
C2 C7 1.512(3) . ?
C2 C3 1.523(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.520(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.526(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.512(4) . ?
C5 C8 1.525(3) . ?
C5 H5 0.9800 . ?
C6 C7 1.527(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 C11 1.494(4) . ?
C11 C16 1.378(4) . ?
C11 C12 1.381(3) . ?
C12 C13 1.375(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.358(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.355(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1A^a H1A^a S1 0.855(10) 2.318(10) 3.088(2) 149.9(10) 1_645 yes
O1B^b H1B^b S1 0.859(10) 2.64(6) 3.177(14) 121(5) 1_645 yes
N1 H1 O3 0.86 1.96 2.631(3) 133.7 . yes
N2 H2A O2A^a 0.86 2.47 3.306(4) 166.1 1_465 yes
N2 H2A O2B^b 0.86 2.41 3.27(2) 177.4 1_465 yes
C12 H12 O2A^a 0.93 2.36 3.173(4) 145.5 1_465 yes
C12 H12 O2B^b 0.93 2.13 3.003(10) 156.5 1_465 yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2A C1 C2 C7 -20.8(5) . . . . ?
O2B C1 C2 C7 9.2(16) . . . . ?
O1B C1 C2 C7 -157.6(11) . . . . ?
O1A C1 C2 C7 157.3(3) . . . . ?
O2A C1 C2 C3 103.8(4) . . . . ?
O2B C1 C2 C3 133.8(15) . . . . ?
O1B C1 C2 C3 -33.0(11) . . . . ?
O1A C1 C2 C3 -78.1(4) . . . . ?
C7 C2 C3 C4 -58.5(3) . . . . ?
C1 C2 C3 C4 175.1(2) . . . . ?
C2 C3 C4 C5 56.6(3) . . . . ?
C3 C4 C5 C6 -54.6(3) . . . . ?
C3 C4 C5 C8 -178.8(2) . . . . ?
C8 C5 C6 C7 176.4(2) . . . . ?
C4 C5 C6 C7 54.7(3) . . . . ?
C1 C2 C7 C6 -177.2(2) . . . . ?
C3 C2 C7 C6 58.5(3) . . . . ?
C5 C6 C7 C2 -57.2(3) . . . . ?
C9 N1 C8 C5 179.2(2) . . . . ?
C6 C5 C8 N1 64.4(3) . . . . ?
C4 C5 C8 N1 -173.1(2) . . . . ?
C8 N1 C9 N2 178.2(2) . . . . ?
C8 N1 C9 S1 -2.0(4) . . . . ?
C10 N2 C9 N1 -4.5(4) . . . . ?
C10 N2 C9 S1 175.7(2) . . . . ?
C9 N2 C10 O3 4.0(4) . . . . ?
C9 N2 C10 C11 -176.4(2) . . . . ?
O3 C10 C11 C16 6.6(4) . . . . ?
N2 C10 C11 C16 -173.0(3) . . . . ?
O3 C10 C11 C12 -170.8(3) . . . . ?
N2 C10 C11 C12 9.6(4) . . . . ?
C16 C11 C12 C13 1.4(4) . . . . ?
C10 C11 C12 C13 178.8(3) . . . . ?
C11 C12 C13 C14 -1.0(5) . . . . ?
C12 C13 C14 C15 -0.4(5) . . . . ?
C13 C14 C15 C16 1.4(5) . . . . ?
C14 C15 C16 C11 -0.9(5) . . . . ?
C12 C11 C16 C15 -0.5(5) . . . . ?
C10 C11 C16 C15 -178.1(3) . . . . ?
