#------------------------------------------------------------------------------
#$Date: 2022-03-18 05:10:18 +0200 (Fri, 18 Mar 2022) $
#$Revision: 273776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/40/2244057.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2244057
loop_
_publ_author_name
'Çelikesir, Sevim Türktekin'
'Akkurt, Mehmet'
'Shikhaliyev, Namiq Q.'
'Mammadova, Naila A.'
'Suleymanova, Gulnar T.'
'Khrustalev, Victor N.'
'Bhattarai, Ajaya'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 (E)-1-[2,2-dibromo-1-(2-nitrophenyl)ethenyl]-2-(4-fluorophenyl)diazene
;
_journal_coeditor_code           HB8012
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205698902200278X
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C14 H8 Br2 F N3 O2'
_chemical_formula_moiety         'C14 H8 Br2 F N3 O2'
_chemical_formula_sum            'C14 H8 Br2 F N3 O2'
_chemical_formula_weight         429.05
_chemical_name_systematic
;
(E)-1-[2,2-Dibromo-1-(2-nitrophenyl)ethenyl]-2-(4-fluorophenyl)diazene
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.8700(4)
_cell_length_b                   15.2915(4)
_cell_length_c                   13.1030(4)
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.29
_cell_measurement_theta_min      2.46
_cell_volume                     2979.42(14)
_computing_cell_refinement
;
SAINT (Bruker, 2018)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2018)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            87568
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.582
_diffrn_reflns_theta_min         2.463
_diffrn_source                   'fine-focus sealed X-Ray tube'
_exptl_absorpt_coefficient_mu    5.462
_exptl_absorpt_correction_T_max  0.1151
_exptl_absorpt_correction_T_min  0.0472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            'light orange'
_exptl_crystal_density_diffrn    1.913
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.834
_refine_diff_density_min         -0.459
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         5429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0230
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0274P)²+1.6564P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0547
_refine_ls_wR_factor_ref         0.0572
_reflns_number_gt                4773
_reflns_number_total             5429
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb8012sup1.cif
_cod_data_source_block           I
_cod_database_code               2244057
_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   0.141
_shelx_estimated_absorpt_t_max   0.408
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, y-1/2, -z-1/2'
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 0.62265(2) 0.95963(2) 0.16792(2) 0.02193(4) Uani d 1 . .
Br Br2 0.64744(2) 1.02154(2) 0.39424(2) 0.02154(4) Uani d 1 . .
F F1 0.61074(8) 0.42468(7) 0.03550(8) 0.0350(2) Uani d 1 . .
O O1 0.79994(8) 0.81157(8) 0.37024(8) 0.0279(2) Uani d 1 . .
O O2 0.82768(8) 0.70323(8) 0.47212(9) 0.0279(2) Uani d 1 . .
N N1 0.78022(8) 0.76388(8) 0.44249(9) 0.0204(2) Uani d 1 . .
N N2 0.61421(8) 0.77830(8) 0.26409(9) 0.0173(2) Uani d 1 . .
N N3 0.61871(8) 0.70235(8) 0.30197(9) 0.0180(2) Uani d 1 . .
C C1 0.62788(9) 0.92776(9) 0.30578(10) 0.0172(2) Uani d 1 . .
C C2 0.62325(9) 0.84437(9) 0.33887(9) 0.0163(2) Uani d 1 . .
C C3 0.62473(9) 0.82188(9) 0.44946(10) 0.0160(2) Uani d 1 . .
C C4 0.69718(9) 0.78201(9) 0.49868(10) 0.0167(2) Uani d 1 . .
C C5 0.69526(10) 0.75800(9) 0.60064(10) 0.0198(2) Uani d 1 . .
H H5 0.745761 0.730610 0.631466 0.024 Uiso calc 1 . .
C C6 0.61793(10) 0.77479(10) 0.65687(10) 0.0216(3) Uani d 1 . .
H H6 0.615605 0.760257 0.727309 0.026 Uiso calc 1 . .
C C7 0.54428(10) 0.81279(10) 0.60985(10) 0.0221(3) Uani d 1 . .
H H7 0.491119 0.823434 0.648092 0.026 Uiso calc 1 . .
C C8 0.54741(10) 0.83559(9) 0.50689(10) 0.0195(2) Uani d 1 . .
H H8 0.495992 0.860845 0.475544 0.023 Uiso calc 1 . .
C C9 0.61222(9) 0.63404(9) 0.22921(10) 0.0173(2) Uani d 1 . .
C C10 0.62860(10) 0.55039(9) 0.26748(11) 0.0214(3) Uani d 1 . .
H H10 0.640277 0.542361 0.338142 0.026 Uiso calc 1 . .
C C11 0.62783(11) 0.47892(10) 0.20219(13) 0.0253(3) Uani d 1 . .
H H11 0.639299 0.421601 0.226931 0.030 Uiso calc 1 . .
C C12 0.60996(11) 0.49353(11) 0.10055(12) 0.0245(3) Uani d 1 . .
C C13 0.59060(10) 0.57525(10) 0.06081(11) 0.0224(3) Uani d 1 . .
H H13 0.577105 0.582364 -0.009565 0.027 Uiso calc 1 . .
C C14 0.59139(10) 0.64622(9) 0.12606(10) 0.0194(2) Uani d 1 . .
H H14 0.577851 0.703011 0.101002 0.023 Uiso calc 1 . .
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'
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
O2 N1 O1 . . 123.62(13) ?
O2 N1 C4 . . 117.94(13) ?
O1 N1 C4 . . 118.41(12) ?
N3 N2 C2 . . 112.28(11) ?
N2 N3 C9 . . 114.15(11) ?
C2 C1 Br2 . . 122.32(10) ?
C2 C1 Br1 . . 123.65(10) ?
Br2 C1 Br1 . . 113.92(7) ?
C1 C2 N2 . . 117.24(12) ?
C1 C2 C3 . . 122.03(12) ?
N2 C2 C3 . . 120.71(12) ?
C8 C3 C4 . . 117.01(12) ?
C8 C3 C2 . . 118.66(12) ?
C4 C3 C2 . . 124.19(12) ?
C5 C4 C3 . . 123.04(13) ?
C5 C4 N1 . . 116.88(12) ?
C3 C4 N1 . . 120.08(12) ?
C4 C5 C6 . . 118.63(13) ?
C4 C5 H5 . . 120.7 ?
C6 C5 H5 . . 120.7 ?
C7 C6 C5 . . 119.75(12) ?
C7 C6 H6 . . 120.1 ?
C5 C6 H6 . . 120.1 ?
C6 C7 C8 . . 120.61(13) ?
C6 C7 H7 . . 119.7 ?
C8 C7 H7 . . 119.7 ?
C3 C8 C7 . . 120.92(13) ?
C3 C8 H8 . . 119.5 ?
C7 C8 H8 . . 119.5 ?
C10 C9 C14 . . 120.52(13) ?
C10 C9 N3 . . 114.96(12) ?
C14 C9 N3 . . 124.52(12) ?
C11 C10 C9 . . 119.93(14) ?
C11 C10 H10 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
C12 C11 C10 . . 118.05(14) ?
C12 C11 H11 . . 121.0 ?
C10 C11 H11 . . 121.0 ?
F1 C12 C11 . . 118.75(14) ?
F1 C12 C13 . . 117.83(13) ?
C11 C12 C13 . . 123.42(14) ?
C14 C13 C12 . . 118.34(13) ?
C14 C13 H13 . . 120.8 ?
C12 C13 H13 . . 120.8 ?
C13 C14 C9 . . 119.68(13) ?
C13 C14 H14 . . 120.2 ?
C9 C14 H14 . . 120.2 ?
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 . 1.8725(13) ?
Br2 C1 . 1.8667(13) ?
F1 C12 . 1.3546(17) ?
O1 N1 . 1.2304(17) ?
O2 N1 . 1.2284(16) ?
N1 C4 . 1.4641(18) ?
N2 N3 . 1.2647(16) ?
N2 C2 . 1.4138(17) ?
N3 C9 . 1.4175(17) ?
C1 C2 . 1.3486(19) ?
C2 C3 . 1.4895(18) ?
C3 C8 . 1.3900(19) ?
C3 C4 . 1.3958(18) ?
C4 C5 . 1.3859(18) ?
C5 C6 . 1.390(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.384(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.3942(18) ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
C9 C10 . 1.3953(19) ?
C9 C14 . 1.3992(19) ?
C10 C11 . 1.388(2) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.376(2) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.384(2) ?
C13 C14 . 1.382(2) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
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 O1 4_665 0.95 2.51 3.3244(18) 144 yes
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
C2 N2 N3 C9 . . . . -178.50(11) ?
Br2 C1 C2 N2 . . . . -175.87(9) ?
Br1 C1 C2 N2 . . . . 0.19(18) ?
Br2 C1 C2 C3 . . . . 5.92(19) ?
Br1 C1 C2 C3 . . . . -178.02(10) ?
N3 N2 C2 C1 . . . . 173.96(13) ?
N3 N2 C2 C3 . . . . -7.80(18) ?
C1 C2 C3 C8 . . . . 75.95(18) ?
N2 C2 C3 C8 . . . . -102.20(16) ?
C1 C2 C3 C4 . . . . -108.63(17) ?
N2 C2 C3 C4 . . . . 73.22(18) ?
C8 C3 C4 C5 . . . . -1.4(2) ?
C2 C3 C4 C5 . . . . -176.84(13) ?
C8 C3 C4 N1 . . . . 178.78(12) ?
C2 C3 C4 N1 . . . . 3.3(2) ?
O2 N1 C4 C5 . . . . 26.58(18) ?
O1 N1 C4 C5 . . . . -151.37(13) ?
O2 N1 C4 C3 . . . . -153.54(13) ?
O1 N1 C4 C3 . . . . 28.51(19) ?
C3 C4 C5 C6 . . . . -0.4(2) ?
N1 C4 C5 C6 . . . . 179.45(13) ?
C4 C5 C6 C7 . . . . 1.6(2) ?
C5 C6 C7 C8 . . . . -1.0(2) ?
C4 C3 C8 C7 . . . . 2.0(2) ?
C2 C3 C8 C7 . . . . 177.74(13) ?
C6 C7 C8 C3 . . . . -0.9(2) ?
N2 N3 C9 C10 . . . . 172.10(13) ?
N2 N3 C9 C14 . . . . -7.8(2) ?
C14 C9 C10 C11 . . . . 2.6(2) ?
N3 C9 C10 C11 . . . . -177.28(14) ?
C9 C10 C11 C12 . . . . -0.5(2) ?
C10 C11 C12 F1 . . . . 178.69(15) ?
C10 C11 C12 C13 . . . . -1.7(3) ?
F1 C12 C13 C14 . . . . -178.71(14) ?
C11 C12 C13 C14 . . . . 1.6(2) ?
C12 C13 C14 C9 . . . . 0.5(2) ?
C10 C9 C14 C13 . . . . -2.6(2) ?
N3 C9 C14 C13 . . . . 177.24(13) ?

_cod_database_fobs_code 2244057
