Synthesis, crystal structure and Hirshfeld surface analysis of 1,1′-[oxybis(ethane-2,1-diyl)]bis(2-methylsulfanyl-1H-benzo[d]imidazole)
Moussaif, Ahmed; El Ghayati, Lhoussaine; Kalonji Mubengayi, Camille; Alsubari, Abdulsalam; Essassi, El Mokhtar; Mague, Joel T.; Ramli, Youssef; Acta Crystallographica Section E Crystallographic Communications 81 (2025) –; doi:10.1107/S2056989025003809

data_2023491
_publ_section_title
;
 Synthesis, crystal structure and Hirshfeld surface analysis of
 1,1&#x2032;-[oxybis(ethane-2,1-diyl)]bis(2-methylsulfanyl-1H-benzo[d]imidazole)
;
_journal_coeditor_code           VM2313
_journal_issue                   6
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989025003809
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          'C20 H22 N4 O S2'
_chemical_formula_moiety         'C20 H22 N4 O S2'
_chemical_formula_sum            'C20 H22 N4 O S2'
_chemical_formula_weight         398.53
_chemical_name_systematic
1,1'-[Oxybis(ethane-2,1-diyl)]bis(2-methylsulfanyl-1<i>H</i>-benzo[<i>d</i>]imidazole)
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_cell_angle_alpha                109.206(2)
_cell_angle_beta                 101.687(2)
_cell_angle_gamma                107.789(2)
_cell_formula_units_Z            4
_cell_length_a                   10.6654(12)
_cell_length_b                   13.5974(15)
_cell_length_c                   15.7917(17)
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.012
_cell_measurement_theta_min      2.578
_cell_volume                     1938.8(4)
_computing_cell_refinement
;
<i>SAINT</i> (Bruker, 2015)
;
_computing_data_collection
;
<i>APEX3</i> (Bruker, 2015)
;
_computing_data_reduction
;
<i>SAINT</i> (Bruker, 2015)
;
_computing_molecular_graphics
;
<i>DIAMOND</i> (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
<i>SHELXTL</i> (Sheldrick, 2008)
;
_computing_structure_refinement
;
<i>SHELXL2019/1</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'BrukerSmart APEX diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_av_unetI/netI     0.0946
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            36334
_diffrn_reflns_theta_full        28.000
_diffrn_reflns_theta_max         29.491
_diffrn_reflns_theta_min         1.732
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Krause <i>et al.</i>, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.181
_refine_diff_density_max         1.320
_refine_diff_density_min         -1.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         10449
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0678
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1077P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1873
_refine_ls_wR_factor_ref         0.1987
_reflns_number_gt                5628
_reflns_number_total             10449
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            vm2313.cif
_cod_data_source_block           I
_cod_database_code               2023491
_shelx_estimated_absorpt_t_min   0.903
_shelx_hkl_checksum              16278
_shelx_res_checksum              91388