Synthesis and crystal structure analysis of 1-ethyl-1,3-dihydro-2H-benzo[d]imidazole-2-thione
Gurbanov, Atash V.; Guseinov, Firudin I.; Samigullina, Aida I.; Hökelek, Tuncer; Hasanov, Khudayar I.; Javadzade, Tahir A.; Belay, Alebel N.; Acta Crystallographica Section E Crystallographic Communications 81 (2025) –; doi:10.1107/S2056989025000519

data_2023365
_publ_section_title
;
 Synthesis and crystal structure analysis of
 1-ethyl-1,3-dihydro-2H-benzo[d]imidazole-2-thione
;
_journal_coeditor_code           PK2714
_journal_issue                   2
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989025000519
_journal_volume                  81
_journal_year                    2025
_chemical_absolute_configuration unknown
_chemical_formula_iupac          'C9 H10 N2 S'
_chemical_formula_moiety         'C9 H10 N2 S'
_chemical_formula_sum            'C9 H10 N2 S'
_chemical_formula_weight         178.25
_chemical_name_systematic
;
1-Ethyl-1,3-dihydro-2<i>H</i>-benzo[<i>d</i>]imidazole-2-thione
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.4512(5)
_cell_length_b                   14.77990(12)
_cell_length_c                   15.89120(11)
_cell_measurement_reflns_used    18990
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      79.0060
_cell_measurement_theta_min      4.0570
_cell_volume                     1750.07(12)
_computing_cell_refinement
;
<i>CrysAlisPRO</i> (Rigaku OD, 2023)
;
_computing_data_collection
;
<i>CrysAlisPRO</i> (Rigaku OD, 2023)
;
_computing_data_reduction
;
<i>CrysAlisPRO</i> (Rigaku OD, 2023)
;
_computing_molecular_graphics
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>, 2009)
;
_computing_publication_material
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>, 2009)
;
_computing_structure_refinement
;
<i>SHELXL2018</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT2014</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      99.9(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector'
_diffrn_measurement_method       '\w scans'
_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  0.0348
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23801
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.527
_diffrn_reflns_theta_min         4.085
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.803
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.405
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(<i>CrysAlis PRO</i>; Rigaku OD, 2023)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.210
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.454(16)
_refine_ls_extinction_coef       0.0010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick 2015b)
;
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0257
_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^)+(0.0359P)^2^+0.5853P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0690
_reflns_number_gt                3779
_reflns_number_total             3799
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            pk2714.cif
_cod_data_source_block           I
_cod_original_cell_volume        1750.06(12)
_cod_database_code               2023365
_shelx_estimated_absorpt_t_min   0.393
_shelx_estimated_absorpt_t_max   0.647
_shelx_hkl_checksum              41604
_shelx_res_checksum              12165