Formation of chalcogen-bonding interactions and their role in the <i>trans</i>-<i>trans</i> conformation of thiourea.
Inoue, Takumi; Morita, Nami; Amijima, Yui; Sakai, Rika; Hamada, Shohei; Nakamura, Seikou; Kobayashi, Yusuke; Furuta, Takumi; Organic & biomolecular chemistry 22 (2024) 5301–5305; doi:10.1039/d4ob00723a

data_7159984
_publ_section_title
;
 Formation of chalcogen-bonding interactions and their role in the
 <i>trans</i>-<i>trans</i> conformation of thiourea.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5301
_journal_page_last               5305
_journal_paper_doi               10.1039/d4ob00723a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C17 H12 N2 S3'
_chemical_formula_sum            'C17 H12 N2 S3'
_chemical_formula_weight         340.47
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-04-16 deposited with the CCDC.	2024-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.472(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.60550(10)
_cell_length_b                   7.63800(10)
_cell_length_c                   34.1020(6)
_cell_measurement_reflns_used    8746
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.2120
_cell_measurement_theta_min      5.1570
_cell_volume                     1459.59(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -60.00 -30.00   0.50    0.25    -- -103.00  57.00 150.00   60
  2  \w    -60.00 -30.00   0.50    0.25    -- -103.00  57.00  60.00   60
  3  \w    -21.00  28.00   0.50    0.10    --  -47.88  19.00  60.00   98
  4  \w    -21.00  28.00   0.50    0.10    --  -47.88  19.00  30.00   98
  5  \w    -21.00  28.00   0.50    0.10    --  -47.88  19.00 -60.00   98
  6  \w    -60.00 -30.00   0.50    0.25    -- -103.00  57.00 -60.00   60
  7  \w    -60.00 -30.00   0.50    0.25    -- -103.00  57.00 120.00   60
  8  \w    -60.00 -30.00   0.50    0.25    -- -103.00  57.00  90.00   60
  9  \w    -60.00 -30.00   0.50    0.25    -- -103.00  57.00  30.00   60
 10  \w    -85.00  -2.00   0.50    0.10    --  -47.88 111.00 -70.00  166
 11  \w   -112.00 -33.00   0.50    0.25    -- -103.00 125.00-150.00  158
 12  \w   -108.00 -34.00   0.50    0.25    -- -103.00 111.00 -70.00  148
 13  \w   -172.00 -81.00   0.50    0.25    -- -103.00-111.00-163.00  182
 14  \w   -120.00 -25.00   0.50    0.10    --  -47.88 -77.00 -90.00  190
 15  \w   -120.00 -33.00   0.50    0.10    --  -47.88 -57.00   0.00  174
 16  \w   -121.00 -63.00   0.50    0.10    --  -47.88 -38.00  30.00  116
 17  \w   -120.00 -33.00   0.50    0.10    --  -47.88 -57.00 120.00  174
 18  \w     37.00  70.00   0.50    0.25    --  109.06 -57.00-150.00   66
 19  \w      9.00  85.00   0.50    0.10    --   47.88-111.00-163.00  152
 20  \w     37.00  70.00   0.50    0.25    --  109.06 -57.00-180.00   66
 21  \w     40.00 108.00   0.50    0.25    --  109.06-111.00-163.00  136
 22  \w     37.00  70.00   0.50    0.25    --  109.06 -57.00  90.00   66
 23  \w     96.00 178.00   0.50    0.25    --  109.06  38.00  90.00  164
 24  \w     88.00 178.00   0.50    0.25    --  109.06 111.00 -70.00  180
 25  \w     96.00 178.00   0.50    0.25    --  109.06  38.00 -90.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0152702000
_diffrn_orient_matrix_UB_12      -0.0903953000
_diffrn_orient_matrix_UB_13      -0.0402437000
_diffrn_orient_matrix_UB_21      0.0551442000
_diffrn_orient_matrix_UB_22      -0.1755538000
_diffrn_orient_matrix_UB_23      0.0205649000
_diffrn_orient_matrix_UB_31      -0.2688436000
_diffrn_orient_matrix_UB_32      -0.0411060000
_diffrn_orient_matrix_UB_33      0.0007494000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            14469
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.904
_diffrn_reflns_theta_min         2.592
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.63a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_preparation       concentration
_exptl_crystal_recrystallization_method acetone
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2954
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0367P)^2^+1.9640P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0953
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2828
_reflns_number_total             2954
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00723a2.cif
_cod_data_source_block           benzothiophene-thiourea
_cod_depositor_comments          'Adding full bibliography for 7159984.cif.'
_cod_database_code               7159984
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C17H12N2S3
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N004(H004), N005(H005), C007(H007), C009(H009), C00E(H00E), C00F(H00F),
 C00G(H00G), C00H(H00H), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M)
;
_shelx_res_checksum              91580
_olex2_exptl_crystal_mounting_method 50
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.411
_oxdiff_exptl_absorpt_empirical_full_min 0.686