Crystal structure and Hirshfeld surface analysis of 4-[4-(1<i>H</i>-benzo[<i>d</i>]imidazol-2-yl)phenoxy]phthalonitrile dimethyl sulfoxide monosolvate
Demir Kanmazalp, Sibel; Şen, Pınar; Dege, Necmi; Yildiz, Salih Zeki; Ozdemir, Namık; Golenya, Irina A.; Acta Crystallographica Section E 75 (2019) 780–784; doi:10.1107/S2056989019006510

data_2242936
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 4-[4-(1<i>H</i>-benzo[<i>d</i>]imidazol-2-yl)phenoxy]phthalonitrile
 dimethyl sulfoxide monosolvate
;
_journal_coeditor_code           WM5496
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              780
_journal_page_last               784
_journal_paper_doi               10.1107/S2056989019006510
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C21 H12 N4 O1, C2 H6 O S'
_chemical_formula_moiety         'C21 H12 N4 O1, C2 H6 O S'
_chemical_formula_sum            'C23 H18 N4 O2 S'
_chemical_formula_weight         414.47
_chemical_name_systematic
;
4-[4-(1<i>H</i>-Benzo[<i>d</i>]imidazole-2-yl)phenoxy]phthalonitrile
dimethyl sulfoxide monosolvate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.9154(11)
_cell_length_b                   11.4208(6)
_cell_length_c                   8.8938(6)
_cell_measurement_reflns_used    9474
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.03
_cell_measurement_theta_min      1.78
_cell_volume                     2124.5(2)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_reduction
;
X-RED32 (Stoe & Cie, 2002)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae <i>et al.</i>,
2006)
;
_computing_publication_material
;
SHELXL2018 (Sheldrick, 2015b), WinGX (Farrugia, 2012) and PLATON
(Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15225
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.080
_diffrn_reflns_theta_min         2.032
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           45
_diffrn_source_power             2.25
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.9769
_exptl_absorpt_correction_T_min  0.9655
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(X-RED32; Stoe & Cie, 2002)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       prism
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.563
_exptl_crystal_size_min          0.470
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.119
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 771 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   -0.02(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.833
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4660
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.833
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0421
_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^)+(0.0409P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0976
_reflns_number_gt                2281
_reflns_number_total             4660
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5496sup1.cif
_cod_data_source_block           I
_cod_database_code               2242936
_cod_database_fobs_code          2242936
_shelx_hkl_checksum              64107
_shelx_res_checksum              40787