##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2018/3'
_chemical_name_systematic
;
(E)-1-(4-Bromophenyl)-2-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]diazene
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H8 Br Cl2 N3 O2'
_chemical_formula_sum     'C14 H8 Br Cl2 N3 O2'
_chemical_formula_iupac     'C14 H8 Br Cl2 N3 O2'
_chemical_formula_weight     401.04
_chemical_melting_point     ?
_chemical_absolute_configuration     ?
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P n a 21'
_space_group_name_Hall     'P 2c -2n'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    '-x+1/2, y+1/2, z+1/2'
    'x+1/2, -y+1/2, z'
_cell_length_a     13.9181(7)
_cell_length_b     13.4336(6)
_cell_length_c     8.4080(4)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1572.05(13)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8656
_cell_measurement_theta_min     2.86
_cell_measurement_theta_max     27.00
_cell_measurement_temperature     296(2)
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'orange'
_exptl_crystal_size_max     0.190
_exptl_crystal_size_mid     0.140
_exptl_crystal_size_min     0.080
_exptl_crystal_density_diffrn     1.694
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     792
_exptl_absorpt_coefficient_mu     2.963
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2003)
;
_exptl_absorpt_correction_T_min     0.608
_exptl_absorpt_correction_T_max     0.784
_diffrn_ambient_temperature     296(2)
_diffrn_source     ?
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     23012
_diffrn_reflns_av_R_equivalents     0.0567
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_theta_min     2.858
_diffrn_reflns_theta_max     27.118
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_refine_special_details
;
 Refined as a 2-component inversion twin.
;
_reflns_number_total     3429
_reflns_number_gt     2811
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0463
_refine_ls_R_factor_gt     0.0326
_refine_ls_wR_factor_gt     0.0743
_refine_ls_wR_factor_ref     0.0814
_refine_ls_goodness_of_fit_ref     1.020
_refine_ls_restrained_S_all     1.020
_refine_ls_number_reflns     3429
_refine_ls_number_parameters     200
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0253P)²+0.7719P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.308
_refine_diff_density_min     -0.504
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
 Refined as an inversion twin
;
_refine_ls_abs_structure_Flack     0.008(13)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX3 (Bruker, 2007)
;
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_structure_solution
;
SHELXT2016/6 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2016/6 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.4004(2) 0.5082(3) 0.5333(5) 0.0393(8) Uani d 1 . .
    C C2 0.3711(3) 0.4164(3) 0.4764(6) 0.0478(10) Uani d 1 . .
    H H2 0.309463 0.408665 0.435584 0.057 Uiso calc 1 . .
    C C3 0.4334(3) 0.3360(3) 0.4803(6) 0.0545(11) Uani d 1 . .
    H H3 0.414420 0.274430 0.440786 0.065 Uiso calc 1 . .
    C C4 0.5228(3) 0.3483(3) 0.5428(6) 0.0481(9) Uani d 1 . .
    C C5 0.5526(3) 0.4381(4) 0.6048(7) 0.0582(13) Uani d 1 . .
    H H5 0.613115 0.444124 0.650896 0.070 Uiso calc 1 . .
    C C6 0.4915(3) 0.5191(3) 0.5976(6) 0.0539(12) Uani d 1 . .
    H H6 0.511337 0.580727 0.635893 0.065 Uiso calc 1 . .
    C C7 0.1912(2) 0.6569(2) 0.5030(5) 0.0378(8) Uani d 1 . .
    C C8 0.0975(3) 0.6351(3) 0.4948(6) 0.0477(10) Uani d 1 . .
    C C9 0.2272(3) 0.7616(2) 0.5010(5) 0.0345(7) Uani d 1 . .
    C C10 0.2658(3) 0.8034(3) 0.6372(5) 0.0437(9) Uani d 1 . .
    H H10 0.270870 0.765504 0.729433 0.052 Uiso calc 1 . .
    C C11 0.2966(3) 0.9009(3) 0.6369(5) 0.0442(9) Uani d 1 . .
    H H11 0.321785 0.929565 0.728509 0.053 Uiso calc 1 . .
    C C12 0.2896(2) 0.9547(3) 0.4988(5) 0.0374(8) Uani d 1 . .
    C C13 0.2538(4) 0.9149(3) 0.3622(5) 0.0511(11) Uani d 1 . .
    H H13 0.250600 0.952658 0.269651 0.061 Uiso calc 1 . .
    C C14 0.2221(3) 0.8170(3) 0.3637(5) 0.0491(10) Uani d 1 . .
    H H14 0.197279 0.788772 0.271406 0.059 Uiso calc 1 . .
    N N1 0.3411(2) 0.5954(2) 0.5291(5) 0.0427(7) Uani d 1 . .
    N N2 0.2537(2) 0.5747(2) 0.5107(4) 0.0403(7) Uani d 1 . .
    N N3 0.3201(2) 1.0595(2) 0.4987(5) 0.0483(8) Uani d 1 . .
    O O1 0.3418(3) 1.0978(3) 0.6245(5) 0.0769(11) Uani d 1 . .
    O O2 0.3240(4) 1.1036(3) 0.3734(5) 0.0863(14) Uani d 1 . .
    Cl Cl1 0.05489(8) 0.51572(8) 0.4988(2) 0.0743(4) Uani d 1 . .
    Cl Cl2 0.00955(8) 0.72322(9) 0.4870(2) 0.0713(4) Uani d 1 . .
    Br Br1 0.60741(4) 0.23804(4) 0.54965(11) 0.0809(2) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C2 . 1.384(5) ?
    C1 C6 . 1.385(6) ?
    C1 N1 . 1.434(4) ?
    C2 C3 . 1.386(6) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.361(6) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.377(6) ?
    C4 Br1 . 1.893(4) ?
    C5 C6 . 1.384(6) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.338(5) ?
    C7 N2 . 1.407(4) ?
    C7 C9 . 1.493(4) ?
    C8 Cl2 . 1.705(4) ?
    C8 Cl1 . 1.710(4) ?
    C9 C14 . 1.376(6) ?
    C9 C10 . 1.384(6) ?
    C10 C11 . 1.378(6) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.371(6) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.361(6) ?
    C12 N3 . 1.470(4) ?
    C13 C14 . 1.387(6) ?
    C13 H13 . 0.9300 ?
    C14 H14 . 0.9300 ?
    N1 N2 . 1.257(4) ?
    N3 O2 . 1.209(5) ?
    N3 O1 . 1.214(5) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 C1 C6 . . 120.0(4) ?
    C2 C1 N1 . . 123.3(3) ?
    C6 C1 N1 . . 116.7(3) ?
    C1 C2 C3 . . 120.1(4) ?
    C1 C2 H2 . . 120.0 ?
    C3 C2 H2 . . 120.0 ?
    C4 C3 C2 . . 119.1(4) ?
    C4 C3 H3 . . 120.4 ?
    C2 C3 H3 . . 120.4 ?
    C3 C4 C5 . . 121.9(4) ?
    C3 C4 Br1 . . 119.0(3) ?
    C5 C4 Br1 . . 119.1(3) ?
    C4 C5 C6 . . 119.1(4) ?
    C4 C5 H5 . . 120.4 ?
    C6 C5 H5 . . 120.4 ?
    C5 C6 C1 . . 119.8(4) ?
    C5 C6 H6 . . 120.1 ?
    C1 C6 H6 . . 120.1 ?
    C8 C7 N2 . . 115.7(3) ?
    C8 C7 C9 . . 122.2(3) ?
    N2 C7 C9 . . 122.2(3) ?
    C7 C8 Cl2 . . 123.3(3) ?
    C7 C8 Cl1 . . 122.8(3) ?
    Cl2 C8 Cl1 . . 113.8(2) ?
    C14 C9 C10 . . 119.7(3) ?
    C14 C9 C7 . . 120.1(3) ?
    C10 C9 C7 . . 120.2(3) ?
    C11 C10 C9 . . 120.3(4) ?
    C11 C10 H10 . . 119.8 ?
    C9 C10 H10 . . 119.8 ?
    C12 C11 C10 . . 118.7(4) ?
    C12 C11 H11 . . 120.6 ?
    C10 C11 H11 . . 120.6 ?
    C13 C12 C11 . . 122.2(3) ?
    C13 C12 N3 . . 118.8(4) ?
    C11 C12 N3 . . 119.0(4) ?
    C12 C13 C14 . . 118.8(4) ?
    C12 C13 H13 . . 120.6 ?
    C14 C13 H13 . . 120.6 ?
    C9 C14 C13 . . 120.3(4) ?
    C9 C14 H14 . . 119.9 ?
    C13 C14 H14 . . 119.9 ?
    N2 N1 C1 . . 112.3(3) ?
    N1 N2 C7 . . 115.5(3) ?
    O2 N3 O1 . . 122.7(3) ?
    O2 N3 C12 . . 118.8(4) ?
    O1 N3 C12 . . 118.5(4) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 C3 . . . . -1.5(7) ?
    N1 C1 C2 C3 . . . . 178.2(4) ?
    C1 C2 C3 C4 . . . . 1.0(7) ?
    C2 C3 C4 C5 . . . . 1.1(8) ?
    C2 C3 C4 Br1 . . . . 179.5(4) ?
    C3 C4 C5 C6 . . . . -2.7(8) ?
    Br1 C4 C5 C6 . . . . 179.0(4) ?
    C4 C5 C6 C1 . . . . 2.1(8) ?
    C2 C1 C6 C5 . . . . 0.0(7) ?
    N1 C1 C6 C5 . . . . -179.8(4) ?
    N2 C7 C8 Cl2 . . . . 179.2(3) ?
    C9 C7 C8 Cl2 . . . . -1.9(7) ?
    N2 C7 C8 Cl1 . . . . 1.8(6) ?
    C9 C7 C8 Cl1 . . . . -179.4(3) ?
    C8 C7 C9 C14 . . . . -70.7(6) ?
    N2 C7 C9 C14 . . . . 108.1(5) ?
    C8 C7 C9 C10 . . . . 109.3(5) ?
    N2 C7 C9 C10 . . . . -71.9(5) ?
    C14 C9 C10 C11 . . . . 1.7(7) ?
    C7 C9 C10 C11 . . . . -178.3(4) ?
    C9 C10 C11 C12 . . . . -0.9(7) ?
    C10 C11 C12 C13 . . . . -0.4(7) ?
    C10 C11 C12 N3 . . . . 178.4(4) ?
    C11 C12 C13 C14 . . . . 1.0(7) ?
    N3 C12 C13 C14 . . . . -177.9(4) ?
    C10 C9 C14 C13 . . . . -1.2(7) ?
    C7 C9 C14 C13 . . . . 178.8(4) ?
    C12 C13 C14 C9 . . . . -0.1(7) ?
    C2 C1 N1 N2 . . . . 18.3(6) ?
    C6 C1 N1 N2 . . . . -161.9(4) ?
    C1 N1 N2 C7 . . . . -179.1(3) ?
    C8 C7 N2 N1 . . . . -175.4(4) ?
    C9 C7 N2 N1 . . . . 5.7(5) ?
    C13 C12 N3 O2 . . . . -9.3(6) ?
    C11 C12 N3 O2 . . . . 171.8(5) ?
    C13 C12 N3 O1 . . . . 171.9(5) ?
    C11 C12 N3 O1 . . . . -7.0(6) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    C6 H6 Cl2 4_565 0.93 2.92 3.593(5) 130.7 yes
    C8 Cl2 Cg2 4_465 1.705(4) 3.656(2) 4.710(5) 118.31(5) yes
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
data_II
_audit_creation_method     'SHELXL-2018/3'
_journal_date_recd_electronic     2019-05-16
_journal_date_accepted     2019-07-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2019
_journal_volume     75
_journal_issue      8
_journal_page_first     1199
_journal_page_last     1204
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989019010004
_journal_coeditor_code     WM5507
_chemical_name_systematic
;
(E)-1-(4-Chlorophenyl)-2-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]diazene
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H8 Cl3 N3 O2'
_chemical_formula_sum     'C14 H8 Cl3 N3 O2'
_chemical_formula_iupac     'C14 H8 Cl3 N3 O2'
_chemical_formula_weight     356.58
_chemical_melting_point     ?
_chemical_absolute_configuration     ?
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P n a 21'
_space_group_name_Hall     'P 2c -2n'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    '-x+1/2, y+1/2, z+1/2'
    'x+1/2, -y+1/2, z'
_cell_length_a     13.8689(7)
_cell_length_b     13.3674(7)
_cell_length_c     8.3620(5)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1550.24(15)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4206
_cell_measurement_theta_min     2.87
_cell_measurement_theta_max     26.38
_cell_measurement_temperature     296(2)
_exptl_crystal_description     'prisme'
_exptl_crystal_colour     'orange'
_exptl_crystal_size_max     0.170
_exptl_crystal_size_mid     0.140
_exptl_crystal_size_min     0.070
_exptl_crystal_density_diffrn     1.528
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     720
_exptl_absorpt_coefficient_mu     0.600
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2003)
;
_exptl_absorpt_correction_T_min     0.911
_exptl_absorpt_correction_T_max     0.946
_diffrn_ambient_temperature     296(2)
_diffrn_source     ?
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11687
_diffrn_reflns_av_R_equivalents     0.0383
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_theta_min     2.873
_diffrn_reflns_theta_max     26.402
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_refine_special_details     ?
_reflns_number_total     3156
_reflns_number_gt     2547
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0549
_refine_ls_R_factor_gt     0.0369
_refine_ls_wR_factor_gt     0.0831
_refine_ls_wR_factor_ref     0.0914
_refine_ls_goodness_of_fit_ref     1.043
_refine_ls_restrained_S_all     1.043
_refine_ls_number_reflns     3156
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0419P)²+0.3296P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.175
_refine_diff_density_min     -0.246
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 1011 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013).
;
_refine_ls_abs_structure_Flack     0.14(3)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX3 (Bruker, 2007)
;
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_structure_solution
;
SHELXT2016/6 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2016/6 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.9044(2) 0.0035(2) 0.3115(4) 0.0400(8) Uani d 1 . .
    C C2 0.8753(3) -0.0900(2) 0.3650(5) 0.0507(9) Uani d 1 . .
    H H2 0.813001 -0.099076 0.403349 0.061 Uiso calc 1 . .
    C C3 0.9385(3) -0.1694(2) 0.3615(6) 0.0569(10) Uani d 1 . .
    H H3 0.919592 -0.231831 0.399107 0.068 Uiso calc 1 . .
    C C4 1.0294(3) -0.1555(3) 0.3023(5) 0.0532(10) Uani d 1 . .
    C C5 1.0584(3) -0.0645(3) 0.2434(6) 0.0646(12) Uani d 1 . .
    H H5 1.119552 -0.056954 0.199546 0.077 Uiso calc 1 . .
    C C6 0.9962(3) 0.0155(3) 0.2498(6) 0.0607(11) Uani d 1 . .
    H H6 1.015836 0.077758 0.212526 0.073 Uiso calc 1 . .
    C C7 0.6941(2) 0.1515(2) 0.3415(4) 0.0376(7) Uani d 1 . .
    C C8 0.6001(2) 0.1294(2) 0.3491(6) 0.0480(8) Uani d 1 . .
    C C9 0.7299(2) 0.2569(2) 0.3447(5) 0.0364(6) Uani d 1 . .
    C C10 0.7644(3) 0.3003(3) 0.2053(4) 0.0464(9) Uani d 1 . .
    H H10 0.766518 0.263150 0.111319 0.056 Uiso calc 1 . .
    C C11 0.7955(3) 0.3983(3) 0.2056(4) 0.0461(9) Uani d 1 . .
    H H11 0.818819 0.427923 0.112661 0.055 Uiso calc 1 . .
    C C12 0.7913(2) 0.4511(2) 0.3468(5) 0.0386(7) Uani d 1 . .
    C C13 0.7591(3) 0.4093(3) 0.4853(5) 0.0530(10) Uani d 1 . .
    H H13 0.757981 0.446192 0.579602 0.064 Uiso calc 1 . .
    C C14 0.7280(3) 0.3110(3) 0.4834(5) 0.0507(10) Uani d 1 . .
    H H14 0.705639 0.281565 0.577118 0.061 Uiso calc 1 . .
    N N1 0.8441(2) 0.09023(19) 0.3159(4) 0.0446(7) Uani d 1 . .
    N N2 0.75630(18) 0.06882(17) 0.3339(4) 0.0408(6) Uani d 1 . .
    N N3 0.8211(2) 0.55693(19) 0.3468(5) 0.0487(7) Uani d 1 . .
    O O1 0.8400(3) 0.5963(2) 0.2197(4) 0.0754(10) Uani d 1 . .
    O O2 0.8259(3) 0.6004(2) 0.4729(4) 0.0879(13) Uani d 1 . .
    Cl Cl1 1.10869(9) -0.25630(8) 0.2991(2) 0.0857(4) Uani d 1 . .
    Cl Cl2 0.55690(6) 0.00980(6) 0.3445(2) 0.0727(3) Uani d 1 . .
    Cl Cl3 0.51218(7) 0.21874(7) 0.3590(2) 0.0751(4) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C6 . 1.383(5) ?
    C1 C2 . 1.387(5) ?
    C1 N1 . 1.430(4) ?
    C2 C3 . 1.377(5) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.366(6) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.373(6) ?
    C4 Cl1 . 1.740(4) ?
    C5 C6 . 1.374(6) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.339(4) ?
    C7 N2 . 1.404(4) ?
    C7 C9 . 1.493(4) ?
    C8 Cl2 . 1.708(3) ?
    C8 Cl3 . 1.708(3) ?
    C9 C14 . 1.368(5) ?
    C9 C10 . 1.387(5) ?
    C10 C11 . 1.379(5) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.377(5) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.362(6) ?
    C12 N3 . 1.473(4) ?
    C13 C14 . 1.382(5) ?
    C13 H13 . 0.9300 ?
    C14 H14 . 0.9300 ?
    N1 N2 . 1.259(4) ?
    N3 O2 . 1.207(5) ?
    N3 O1 . 1.214(4) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C6 C1 C2 . . 119.5(3) ?
    C6 C1 N1 . . 117.0(3) ?
    C2 C1 N1 . . 123.5(3) ?
    C3 C2 C1 . . 120.2(3) ?
    C3 C2 H2 . . 119.9 ?
    C1 C2 H2 . . 119.9 ?
    C4 C3 C2 . . 119.4(3) ?
    C4 C3 H3 . . 120.3 ?
    C2 C3 H3 . . 120.3 ?
    C3 C4 C5 . . 121.3(3) ?
    C3 C4 Cl1 . . 118.9(3) ?
    C5 C4 Cl1 . . 119.7(3) ?
    C4 C5 C6 . . 119.4(4) ?
    C4 C5 H5 . . 120.3 ?
    C6 C5 H5 . . 120.3 ?
    C5 C6 C1 . . 120.2(4) ?
    C5 C6 H6 . . 119.9 ?
    C1 C6 H6 . . 119.9 ?
    C8 C7 N2 . . 115.3(3) ?
    C8 C7 C9 . . 122.1(3) ?
    N2 C7 C9 . . 122.7(3) ?
    C7 C8 Cl2 . . 123.2(2) ?
    C7 C8 Cl3 . . 122.9(2) ?
    Cl2 C8 Cl3 . . 113.90(19) ?
    C14 C9 C10 . . 119.9(3) ?
    C14 C9 C7 . . 120.5(3) ?
    C10 C9 C7 . . 119.6(3) ?
    C11 C10 C9 . . 120.3(3) ?
    C11 C10 H10 . . 119.9 ?
    C9 C10 H10 . . 119.9 ?
    C12 C11 C10 . . 118.4(3) ?
    C12 C11 H11 . . 120.8 ?
    C10 C11 H11 . . 120.8 ?
    C13 C12 C11 . . 122.2(3) ?
    C13 C12 N3 . . 119.1(3) ?
    C11 C12 N3 . . 118.7(3) ?
    C12 C13 C14 . . 118.9(3) ?
    C12 C13 H13 . . 120.6 ?
    C14 C13 H13 . . 120.6 ?
    C9 C14 C13 . . 120.4(4) ?
    C9 C14 H14 . . 119.8 ?
    C13 C14 H14 . . 119.8 ?
    N2 N1 C1 . . 112.6(2) ?
    N1 N2 C7 . . 114.9(2) ?
    O2 N3 O1 . . 123.0(3) ?
    O2 N3 C12 . . 118.5(3) ?
    O1 N3 C12 . . 118.4(3) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 C3 . . . . 2.1(7) ?
    N1 C1 C2 C3 . . . . -178.0(4) ?
    C1 C2 C3 C4 . . . . -1.1(7) ?
    C2 C3 C4 C5 . . . . -1.3(7) ?
    C2 C3 C4 Cl1 . . . . 179.8(3) ?
    C3 C4 C5 C6 . . . . 2.6(8) ?
    Cl1 C4 C5 C6 . . . . -178.5(4) ?
    C4 C5 C6 C1 . . . . -1.6(8) ?
    C2 C1 C6 C5 . . . . -0.8(7) ?
    N1 C1 C6 C5 . . . . 179.4(4) ?
    N2 C7 C8 Cl2 . . . . -1.8(6) ?
    C9 C7 C8 Cl2 . . . . 179.6(3) ?
    N2 C7 C8 Cl3 . . . . -179.9(3) ?
    C9 C7 C8 Cl3 . . . . 1.4(6) ?
    C8 C7 C9 C14 . . . . 73.1(5) ?
    N2 C7 C9 C14 . . . . -105.4(4) ?
    C8 C7 C9 C10 . . . . -106.3(5) ?
    N2 C7 C9 C10 . . . . 75.2(5) ?
    C14 C9 C10 C11 . . . . -0.9(6) ?
    C7 C9 C10 C11 . . . . 178.5(3) ?
    C9 C10 C11 C12 . . . . 0.0(6) ?
    C10 C11 C12 C13 . . . . 1.1(6) ?
    C10 C11 C12 N3 . . . . -177.8(3) ?
    C11 C12 C13 C14 . . . . -1.1(6) ?
    N3 C12 C13 C14 . . . . 177.7(3) ?
    C10 C9 C14 C13 . . . . 0.9(6) ?
    C7 C9 C14 C13 . . . . -178.5(4) ?
    C12 C13 C14 C9 . . . . 0.1(6) ?
    C6 C1 N1 N2 . . . . 162.9(4) ?
    C2 C1 N1 N2 . . . . -17.0(5) ?
    C1 N1 N2 C7 . . . . 179.0(3) ?
    C8 C7 N2 N1 . . . . 175.4(4) ?
    C9 C7 N2 N1 . . . . -5.9(5) ?
    C13 C12 N3 O2 . . . . 7.8(5) ?
    C11 C12 N3 O2 . . . . -173.3(4) ?
    C13 C12 N3 O1 . . . . -172.4(4) ?
    C11 C12 N3 O1 . . . . 6.5(5) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    C8 Cl3 Cg2 4_455 1.708(3) 3.6154(18) 4.703(3) 119.72(10) yes
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     0.905
_shelx_estimated_absorpt_T_max     0.959
data_global
_journal_date_recd_electronic     2019-05-16
_journal_date_accepted     2019-07-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2019
_journal_volume     75
_journal_issue      8
_journal_page_first     1199
_journal_page_last     1204
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989019010004
_journal_coeditor_code     WM5507
_publ_contact_author_name     'Flavien A. A. Toze'
_publ_contact_author_address
;
Department of Chemistry,
Faculty of Sciences,
University of Douala,
PO Box 24157, Douala,
Republic of Cameroon
;
_publ_contact_author_email     'toflavien@yahoo.fr'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;\
Crystal structures and Hirshfeld surface analyses of the two isotypic compounds
(E)-1-(4-bromophenyl)-2-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]diazene
and
(E)-1-(4-chlorophenyl)-2-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]\
diazene
;
loop_
    _publ_author_name
    _publ_author_address
    'Akkurt, Mehmet'
;
Department of Physics,
Faculty of Sciences,
Erciyes University,
38039 Kayseri,
Turkey
;
    'Namiq Q. Shikhaliyev'
;
Organic Chemistry Department,
Baku State University,
Z. Xalilov str. 23, Az
1148 Baku, Azerbaijan
;
    'Gulnar T. Suleymanova'
;
Organic Chemistry Department,
Baku State University,
Z. Xalilov str. 23, Az
1148 Baku, Azerbaijan
;
    'Gulnare V. Babayeva'
;
Organic Chemistry Department,
Baku State University,
Z. Xalilov str. 23, Az
1148 Baku, Azerbaijan
;
    'Gunay Z. Mammadova'
;
Organic Chemistry Department,
Baku State University,
Z. Xalilov str. 23, Az
1148 Baku, Azerbaijan
;
    'Ayten A. Niyazova'
;
Organic Chemistry Department,
Baku State University,
Z. Xalilov str. 23, Az
1148 Baku, Azerbaijan
;
    'Irada M. Shikhaliyeva'
;
Organic Chemistry Department,
Baku State University,
Z. Xalilov str. 23, Az
1148 Baku, Azerbaijan
;
    'Flavien A. A. Toze'
;
Department of Chemistry,
Faculty of Sciences,
University of Douala,
PO Box 24157, Douala,
Republic of Cameroon
;
_publ_section_synopsis
;
In the crystals of the two isotypic compounds, molecules are linked by weak
halogen--halogen (Br...Cl or Cl...Cl) contacts and C---Cl...π interactions
into sheets lying parallel to the ab plane.
;
