Crystal structures and Hirshfeld surface analyses of the two isotypic compounds (<i>E</i>)-1-(4-bromophenyl)-2-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]diazene and (<i>E</i>)-1-(4-chlorophenyl)-2-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]diazene
Akkurt, Mehmet; Shikhaliyev, Namiq Q.; Suleymanova, Gulnar T.; Babayeva, Gulnare V.; Mammadova, Gunay Z.; Niyazova, Ayten A.; Shikhaliyeva, Irada M.; Toze, Flavien A. A.; Acta Crystallographica Section E 75 (2019) 1199–1204; doi:10.1107/S2056989019010004

data_2243024
_publ_section_title
;
 Crystal structures and Hirshfeld surface analyses of the two isotypic
 compounds
 (<i>E</i>)-1-(4-bromophenyl)-2-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]diazene
 and
 (<i>E</i>)-1-(4-chlorophenyl)-2-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]diazene
;
_journal_coeditor_code           WM5507
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1199
_journal_page_last               1204
_journal_paper_doi               10.1107/S2056989019010004
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C14 H8 Br Cl2 N3 O2'
_chemical_formula_moiety         'C14 H8 Br Cl2 N3 O2'
_chemical_formula_sum            'C14 H8 Br Cl2 N3 O2'
_chemical_formula_weight         401.04
_chemical_name_systematic
;
(<i>E</i>)-1-(4-Bromophenyl)-2-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]diazene
;
_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                   13.9181(7)
_cell_length_b                   13.4336(6)
_cell_length_c                   8.4080(4)
_cell_measurement_reflns_used    8656
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.86
_cell_volume                     1572.05(13)
_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, 2009)
;
_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 0.995
_diffrn_measured_fraction_theta_max 0.996
_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  0.0567
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            23012
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.118
_diffrn_reflns_theta_min         2.858
_exptl_absorpt_coefficient_mu    2.963
_exptl_absorpt_correction_T_max  0.784
_exptl_absorpt_correction_T_min  0.608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2003)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.504
_refine_ls_abs_structure_details
;
 Refined as an inversion twin
;
_refine_ls_abs_structure_Flack   0.008(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3429
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0253P)^2^+0.7719P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0814
_reflns_number_gt                2811
_reflns_number_total             3429
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            wm5507sup1.cif
_cod_data_source_block           I
_cod_database_code               2243024
_cod_database_fobs_code          2243024
_shelx_hkl_checksum              69120
_shelx_res_checksum              61918