Synthesis, crystal structure and Hirshfeld surface analysis of (1<i>H</i>-benzimidazol-2-yl)(morpholin-4-yl)methanethione
Mutalliev, Lukmonjon Z.; Abdullaev, Sirojiddin; Pirnazarova, Nasiba; Obidova, Ibodat; Turgunov, Kambarali; Yakubov, Ubaydullo; Ashurov, Jamshid M.; Elmuradov, Burkhan Zh.; Mamadrakhimov, Azimjon A.; Acta Crystallographica Section E 78 (2022) –; doi:10.1107/S2056989022008933

data_2244161
_publ_section_title
;
 Synthesis, crystal structure and Hirshfeld surface analysis of
 (1<i>H</i>-benzimidazol-2-yl)(morpholin-4-yl)methanethione
;
_journal_coeditor_code           WM5654
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022008933
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C12 H13 N3 O S'
_chemical_formula_moiety         'C12 H13 N3 O S'
_chemical_formula_sum            'C12 H13 N3 O S'
_chemical_formula_weight         247.31
_chemical_melting_point          513(2)
_chemical_name_common
;
2-[(Morpholin-4-yl)carbothioyl]-1<i>H</i>-1,3-benzodiazole
;
_chemical_name_systematic
;
(1<i>H</i>-Benzimidazol-2-yl)(morpholin-4-yl)methanethione
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.661(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1644(2)
_cell_length_b                   15.9237(3)
_cell_length_c                   9.6936(2)
_cell_measurement_reflns_used    4375
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.1310
_cell_measurement_theta_min      5.4640
_cell_volume                     1207.33(5)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_molecular_graphics
;
XP (Siemens, 1994), Mercury (Macrae <i>et al.</i> 2020)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_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 0.994
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_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  0.0217
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5160
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.270
_diffrn_reflns_theta_min         5.515
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.280
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>CrysAlisPro</i>; Rigaku OD, 2020)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          .30
_exptl_crystal_size_mid          .25
_exptl_crystal_size_min          .14
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.191
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 531 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>, 2013)
;
_refine_ls_abs_structure_Flack   -0.001(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         1724
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0301
_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/[\s^2^(Fo^2^)+(0.0448P)^2^+0.2955P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0786
_reflns_number_gt                1692
_reflns_number_total             1724
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5654sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'I a'
_cod_database_code               2244161
_shelx_hkl_checksum              11801
_shelx_res_checksum              96052
_cod_database_fobs_code 2244161