Crystal structure and Hirshfeld surface analysis of 1,3-bis{2,2-dichloro-1-[(<i>E</i>)-phenyldiazenyl]ethenyl}benzene
Shikhaliyev, Namiq Q.; Atioğlu, Zeliha; Akkurt, Mehmet; Ahmadova, Nigar E.; Askerov, Rizvan K.; Bhattarai, Ajaya; Acta Crystallographica Section E 77 (2021) 814–818; doi:10.1107/S2056989021007192

data_2243873
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 1,3-bis{2,2-dichloro-1-[(<i>E</i>)-phenyldiazenyl]ethenyl}benzene
;
_journal_coeditor_code           YK2154
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              814
_journal_page_last               818
_journal_paper_doi               10.1107/S2056989021007192
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C22 H14 Cl4 N4'
_chemical_formula_moiety         'C22 H14 Cl4 N4'
_chemical_formula_sum            'C22 H14 Cl4 N4'
_chemical_formula_weight         476.17
_chemical_name_common
;
1,3-Bis{2,2-dichloro-1-[(<i>E</i>)-phenyldiazenyl]ethenyl}benzene
;
_chemical_name_systematic
(<i>E</i>)-[2,2-Dichloro-1-(3-{2,2-dichloro-1-[(<i>E</i>)-2-phenyldiazen-1-yl]ethenyl}phenyl)ethenyl](phenyl)diazene
_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     difmap
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 108.073(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0289(10)
_cell_length_b                   13.1213(8)
_cell_length_c                   11.1286(7)
_cell_measurement_reflns_used    6439
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.51
_cell_volume                     2225.1(2)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
APEX3 (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
<i>SHELXL2016/6</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT2016/6</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24362
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.408
_diffrn_reflns_theta_min         2.048
_exptl_absorpt_coefficient_mu    0.549
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       prism
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.435
_exptl_crystal_size_mid          0.262
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.250
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0456P)^2^+1.0697P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1117
_reflns_number_gt                3193
_reflns_number_total             4399
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            yk2154sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243873
_shelx_estimated_absorpt_t_min   0.796
_shelx_estimated_absorpt_t_max   0.936
_shelx_hkl_checksum              32632
_shelx_res_checksum              13255
_cod_database_fobs_code 2243873