Crystal structure and Hirshfeld surface analysis of (<i>E</i>)-4-({2,2-dichloro-1-[4-(dimethylamino)phenyl]ethenyl}diazenyl)benzonitrile
Shikhaliyev, Namiq Q.; Atioğlu, Zeliha; Akkurt, Mehmet; Suleymanova, Gulnar T.; Babayeva, Gulnare V.; Mlowe, Sixberth; Acta Crystallographica Section E 77 (2021) –; doi:10.1107/S2056989021009154

data_2243908
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 (<i>E</i>)-4-({2,2-dichloro-1-[4-(dimethylamino)phenyl]ethenyl}diazenyl)benzonitrile
;
_journal_coeditor_code           VM2253
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989021009154
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C17 H14 Cl2 N4'
_chemical_formula_moiety         'C17 H14 Cl2 N4'
_chemical_formula_sum            'C17 H14 Cl2 N4'
_chemical_formula_weight         345.22
_chemical_name_systematic
(<i>E</i>)-4-({2,2-Dichloro-1-[4-(dimethylamino)phenyl]ethenyl}diazenyl)benzonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 104.39(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.396(3)
_cell_length_b                   6.5280(7)
_cell_length_c                   20.758(3)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.0
_cell_volume                     1627.1(5)
_computing_cell_refinement
;
<i>iMosflm</i> (Battye <i>et al.</i>,  2011)
;
_computing_data_collection
;
<i>Marccd</i>(Doyle, 2011)
;
_computing_data_reduction
;
<i>iMosflm</i> (Battye <i>et al.</i>,  2011)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.79475
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21540
_diffrn_reflns_theta_full        28.480
_diffrn_reflns_theta_max         31.015
_diffrn_reflns_theta_min         1.952
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SCALA</i>; Evans, 2006)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.358
_refine_ls_extinction_coef       0.0082(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0535P)^2^+0.5596P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1097
_reflns_number_gt                2913
_reflns_number_total             3712
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            vm2253sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2243908
_shelx_estimated_absorpt_t_min   0.947
_shelx_estimated_absorpt_t_max   0.973
_shelx_hkl_checksum              89149
_shelx_res_checksum              62377
_shelxl_version_number           .2013
_cod_database_fobs_code 2243908