##############################################################################
#                                                                            #
# 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.                                        #
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##############################################################################
data_I
_audit_creation_method     'SHELXL-2018/3'
_journal_date_recd_electronic     2022-03-30
_journal_date_accepted     2022-04-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2022
_journal_volume     78
_journal_issue      5
_journal_page_first     530
_journal_page_last     535
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989022004388
_journal_coeditor_code     WM5642
_publ_contact_author_name     'Ajaya Bhattarai'
_publ_contact_author_address
;
Department of Chemistry,
M.M.A.M.C (Tribhuvan University) Biratnagar,
Nepal
;
_publ_contact_author_email     'ajaya.bhattarai@mmamc.tu.edu.np'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Crystal structure and Hirshfeld surface analysis of
(E)-1-[2,2-dibromo-1-(4-nitrophenyl)ethenyl]-2-(4-fluorophenyl)diazene
;
loop_
    _publ_author_name
    _publ_author_address
    'Zeliha Atioğlu'
;
Department of Aircraft Electrics and Electronics,
School of Applied Sciences,
Cappadocia University,
Mustafapaşa, 50420 Ürgüp,
Nevşehir, Turkey
;
    'Mehmet Akkurt'
;
Department of Physics,
Faculty of Sciences,
Erciyes University,
38039 Kayseri,
Turkey
;
    'Namiq Q. Shikhaliyev'
;
Organic Chemistry Department,
Baku State University, Z. Khalilov str. 23,
AZ 1148 Baku, Azerbaijan
;
    'Naila A. Mammadova'
;
Organic Chemistry Department,
Baku State University, Z. Khalilov str. 23,
AZ 1148 Baku, Azerbaijan
;
    'Gulnara V. Babayeva'
;
Organic Chemistry Department,
Baku State University, Z. Khalilov str. 23,
AZ 1148 Baku, Azerbaijan
Azerbaijan State Pedagogical University,
Uzeyir Hajibeyli str., 68, Baku,
Azerbaijan
;
    'Victor N. Khrustalev'
;
Peoples' Friendship University of Russia,
6 Miklukho-Maklaya, Moscow, Russian Federation
N.D. Zelinsky Institute of Organic Chemistry,
Russian Academy of Sciences, 47 Leninsky Av.,
Moscow, Russian Federation
;
    'Ajaya Bhattarai'
;
Department of Chemistry,
M.M.A.M.C (Tribhuvan University) Biratnagar,
Nepal
;
_publ_section_synopsis
;
C---H...O and C---H...F hydrogen bonds link molecules in the crystal into layers
parallel to (011). The crystal packing is consolidated through C---Br...π and
C---F...π interactions, as well as π--π stacking interactions.
;
_chemical_name_systematic
;
(E)-1-[2,2-Dibromo-1-(4-nitrophenyl)ethenyl]-2-(4-fluorophenyl)diazene
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H8 Br2 F N3 O2'
_chemical_formula_sum     'C14 H8 Br2 F N3 O2'
_chemical_formula_iupac     'C14 H8 Br2 F N3 O2'
_chemical_formula_weight     429.05
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     16.0658(2)
_cell_length_b     7.03290(10)
_cell_length_c     12.7934(2)
_cell_angle_alpha     90
_cell_angle_beta     96.8470(6)
_cell_angle_gamma     90
_cell_volume     1435.21(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9926
_cell_measurement_theta_min     3.17
_cell_measurement_theta_max     33.15
_cell_measurement_temperature     100(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     'light red'
_exptl_crystal_size_max     0.37
_exptl_crystal_size_mid     0.21
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.986
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     832
_exptl_absorpt_coefficient_mu     5.669
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_absorpt_correction_T_min     0.4145
_exptl_absorpt_correction_T_max     0.7465
_diffrn_ambient_temperature     100(2)
_diffrn_source     'fine-focus sealed X-Ray tube'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method     'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean     7.31
_diffrn_reflns_number     44165
_diffrn_reflns_av_R_equivalents     0.1017
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_theta_min     2.554
_diffrn_reflns_theta_max     30.000
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -22
_diffrn_reflns_limit_h_max     22
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     4177
_reflns_number_gt     3809
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0377
_refine_ls_R_factor_gt     0.0344
_refine_ls_wR_factor_gt     0.0926
_refine_ls_wR_factor_ref     0.0955
_refine_ls_goodness_of_fit_ref     1.049
_refine_ls_restrained_S_all     1.049
_refine_ls_number_reflns     4177
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0647P)²+0.5442P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.997
_refine_diff_density_min     -1.043
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
    'F' 'F' 0.0171 0.0103
                         '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, 2018)
;
_computing_cell_refinement
;
SAINT (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2018)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
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
    Br Br1 0.07857(2) 0.35922(3) 0.08663(2) 0.01718(8) Uani d 1 . .
    Br Br2 0.02778(2) 0.28084(3) 0.31239(2) 0.02246(8) Uani d 1 . .
    C C1 0.10911(13) 0.3752(3) 0.23267(15) 0.0143(3) Uani d 1 . .
    C C2 0.18336(12) 0.4450(3) 0.27612(15) 0.0135(3) Uani d 1 . .
    C C3 0.20411(12) 0.4693(3) 0.39184(15) 0.0131(3) Uani d 1 . .
    C C4 0.26892(13) 0.3653(3) 0.44734(16) 0.0151(4) Uani d 1 . .
    H H4 0.301935 0.282209 0.410651 0.018 Uiso calc 1 . .
    C C5 0.28537(13) 0.3827(3) 0.55606(16) 0.0148(3) Uani d 1 . .
    H H5 0.329792 0.313645 0.594394 0.018 Uiso calc 1 . .
    C C6 0.23537(13) 0.5033(3) 0.60701(15) 0.0141(3) Uani d 1 . .
    C C7 0.17169(13) 0.6115(3) 0.55419(16) 0.0158(4) Uani d 1 . .
    H H7 0.139047 0.694455 0.591491 0.019 Uiso calc 1 . .
    C C8 0.15669(12) 0.5958(3) 0.44533(15) 0.0143(3) Uani d 1 . .
    H H8 0.114268 0.670850 0.407127 0.017 Uiso calc 1 . .
    N N1 0.24975(12) 0.5135(2) 0.72236(14) 0.0178(3) Uani d 1 . .
    O O1 0.19544(12) 0.5861(2) 0.76893(13) 0.0259(3) Uani d 1 . .
    O O2 0.31534(11) 0.4454(2) 0.76654(12) 0.0245(3) Uani d 1 . .
    N N2 0.23866(11) 0.4967(2) 0.20300(13) 0.0153(3) Uani d 1 . .
    N N3 0.31074(11) 0.5492(3) 0.24360(14) 0.0165(3) Uani d 1 . .
    C C9 0.36346(12) 0.6039(3) 0.16716(15) 0.0144(3) Uani d 1 . .
    C C10 0.33917(13) 0.6020(3) 0.05795(16) 0.0158(4) Uani d 1 . .
    H H10 0.285307 0.556049 0.030764 0.019 Uiso calc 1 . .
    C C11 0.39360(14) 0.6669(3) -0.00982(16) 0.0177(4) Uani d 1 . .
    H H11 0.377788 0.667540 -0.083780 0.021 Uiso calc 1 . .
    C C12 0.47214(14) 0.7314(3) 0.03294(17) 0.0185(4) Uani d 1 . .
    C C13 0.49862(14) 0.7325(3) 0.13950(18) 0.0203(4) Uani d 1 . .
    H H13 0.553030 0.776322 0.165862 0.024 Uiso calc 1 . .
    C C14 0.44330(14) 0.6675(3) 0.20716(17) 0.0186(4) Uani d 1 . .
    H H14 0.459864 0.666418 0.280965 0.022 Uiso calc 1 . .
    F F1 0.52527(9) 0.7950(2) -0.03383(11) 0.0261(3) 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
    Br1 C1 . 1.878(2) ?
    Br2 C1 . 1.872(2) ?
    C1 C2 . 1.347(3) ?
    C2 N2 . 1.412(3) ?
    C2 C3 . 1.488(3) ?
    C3 C4 . 1.395(3) ?
    C3 C8 . 1.402(3) ?
    C4 C5 . 1.390(3) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.384(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.385(3) ?
    C6 N1 . 1.468(2) ?
    C7 C8 . 1.389(3) ?
    C7 H7 . 0.9500 ?
    C8 H8 . 0.9500 ?
    N1 O1 . 1.225(2) ?
    N1 O2 . 1.232(3) ?
    N2 N3 . 1.266(2) ?
    N3 C9 . 1.421(3) ?
    C9 C14 . 1.397(3) ?
    C9 C10 . 1.405(3) ?
    C10 C11 . 1.380(3) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.390(3) ?
    C11 H11 . 0.9500 ?
    C12 F1 . 1.354(2) ?
    C12 C13 . 1.379(3) ?
    C13 C14 . 1.390(3) ?
    C13 H13 . 0.9500 ?
    C14 H14 . 0.9500 ?
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 Br2 . . 123.06(15) ?
    C2 C1 Br1 . . 123.08(15) ?
    Br2 C1 Br1 . . 113.85(10) ?
    C1 C2 N2 . . 114.61(17) ?
    C1 C2 C3 . . 122.32(17) ?
    N2 C2 C3 . . 123.05(17) ?
    C4 C3 C8 . . 120.02(18) ?
    C4 C3 C2 . . 120.73(17) ?
    C8 C3 C2 . . 119.23(17) ?
    C5 C4 C3 . . 120.28(18) ?
    C5 C4 H4 . . 119.9 ?
    C3 C4 H4 . . 119.9 ?
    C6 C5 C4 . . 118.27(18) ?
    C6 C5 H5 . . 120.9 ?
    C4 C5 H5 . . 120.9 ?
    C5 C6 C7 . . 122.93(18) ?
    C5 C6 N1 . . 118.21(18) ?
    C7 C6 N1 . . 118.85(17) ?
    C6 C7 C8 . . 118.38(18) ?
    C6 C7 H7 . . 120.8 ?
    C8 C7 H7 . . 120.8 ?
    C7 C8 C3 . . 120.04(18) ?
    C7 C8 H8 . . 120.0 ?
    C3 C8 H8 . . 120.0 ?
    O1 N1 O2 . . 123.97(19) ?
    O1 N1 C6 . . 118.25(18) ?
    O2 N1 C6 . . 117.77(17) ?
    N3 N2 C2 . . 114.84(17) ?
    N2 N3 C9 . . 112.81(17) ?
    C14 C9 C10 . . 120.10(19) ?
    C14 C9 N3 . . 115.55(18) ?
    C10 C9 N3 . . 124.33(18) ?
    C11 C10 C9 . . 119.98(19) ?
    C11 C10 H10 . . 120.0 ?
    C9 C10 H10 . . 120.0 ?
    C10 C11 C12 . . 118.29(19) ?
    C10 C11 H11 . . 120.9 ?
    C12 C11 H11 . . 120.9 ?
    F1 C12 C13 . . 118.6(2) ?
    F1 C12 C11 . . 118.07(19) ?
    C13 C12 C11 . . 123.3(2) ?
    C12 C13 C14 . . 118.0(2) ?
    C12 C13 H13 . . 121.0 ?
    C14 C13 H13 . . 121.0 ?
    C13 C14 C9 . . 120.3(2) ?
    C13 C14 H14 . . 119.8 ?
    C9 C14 H14 . . 119.8 ?
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
    Br2 C1 C2 N2 . . . . 175.66(13) ?
    Br1 C1 C2 N2 . . . . -3.1(3) ?
    Br2 C1 C2 C3 . . . . -5.6(3) ?
    Br1 C1 C2 C3 . . . . 175.56(14) ?
    C1 C2 C3 C4 . . . . 115.8(2) ?
    N2 C2 C3 C4 . . . . -65.7(3) ?
    C1 C2 C3 C8 . . . . -63.1(3) ?
    N2 C2 C3 C8 . . . . 115.5(2) ?
    C8 C3 C4 C5 . . . . 1.7(3) ?
    C2 C3 C4 C5 . . . . -177.12(18) ?
    C3 C4 C5 C6 . . . . 0.8(3) ?
    C4 C5 C6 C7 . . . . -2.1(3) ?
    C4 C5 C6 N1 . . . . 176.62(18) ?
    C5 C6 C7 C8 . . . . 1.0(3) ?
    N1 C6 C7 C8 . . . . -177.77(17) ?
    C6 C7 C8 C3 . . . . 1.5(3) ?
    C4 C3 C8 C7 . . . . -2.9(3) ?
    C2 C3 C8 C7 . . . . 175.96(18) ?
    C5 C6 N1 O1 . . . . -164.51(19) ?
    C7 C6 N1 O1 . . . . 14.3(3) ?
    C5 C6 N1 O2 . . . . 14.4(3) ?
    C7 C6 N1 O2 . . . . -166.82(18) ?
    C1 C2 N2 N3 . . . . -175.03(18) ?
    C3 C2 N2 N3 . . . . 6.3(3) ?
    C2 N2 N3 C9 . . . . -178.63(16) ?
    N2 N3 C9 C14 . . . . 178.57(18) ?
    N2 N3 C9 C10 . . . . 0.4(3) ?
    C14 C9 C10 C11 . . . . -1.4(3) ?
    N3 C9 C10 C11 . . . . 176.7(2) ?
    C9 C10 C11 C12 . . . . 0.6(3) ?
    C10 C11 C12 F1 . . . . -179.95(19) ?
    C10 C11 C12 C13 . . . . 0.5(3) ?
    F1 C12 C13 C14 . . . . 179.7(2) ?
    C11 C12 C13 C14 . . . . -0.7(3) ?
    C12 C13 C14 C9 . . . . -0.1(3) ?
    C10 C9 C14 C13 . . . . 1.2(3) ?
    N3 C9 C14 C13 . . . . -177.1(2) ?
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
    C4 H4 O2 4_565 0.95 2.47 3.331(3) 151.00 yes
    C5 H5 F1 2_645 0.95 2.54 3.150(3) 122.00 yes
    C11 H11 O2 1_554 0.95 2.58 3.367(3) 140.00 yes
    C14 H14 F1 4_576 0.95 2.49 3.427(3) 169.00 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     0.228
_shelx_estimated_absorpt_T_max     0.660
