#------------------------------------------------------------------------------
#$Date: 2022-06-17 03:55:22 +0200 (Fri 17 de Jun de 2022) $
#$Revision: 276079 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/41/2244117.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_2244117
loop_
_publ_author_name
'Akkurt, Mehmet'
'Yıldırım, Sema Öztürk'
'Shikhaliyev, Namiq Q.'
'Mammadova, Naila A.'
'Niyazova, Ayten A.'
'Khrustalev, Victor N.'
'Bhattarai, Ajaya'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 (E)-2-(4-bromophenyl)-1-[2,2-dibromo-1-(4-nitrophenyl)ethenyl]diazene
;
_journal_coeditor_code           YK2170
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205698902200620X
_journal_volume                  78
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C14 H8 Br3 N3 O2'
_chemical_formula_moiety         'C14 H8 Br3 N3 O2'
_chemical_formula_sum            'C14 H8 Br3 N3 O2'
_chemical_formula_weight         489.96
_chemical_name_systematic
;
(E)-2-(4-Bromophenyl)-1-[2,2-dibromo-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'
_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            4
_cell_length_a                   13.8678(5)
_cell_length_b                   13.5442(5)
_cell_length_c                   8.3017(3)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.81
_cell_measurement_theta_min      2.88
_cell_volume                     1559.29(10)
_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 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  0.0573
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            75835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.973
_diffrn_reflns_theta_min         2.878
_diffrn_source                   'fine-focus sealed X-Ray tube'
_exptl_absorpt_coefficient_mu    7.770
_exptl_absorpt_correction_T_max  0.1101
_exptl_absorpt_correction_T_min  0.0441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.087
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.405
_refine_diff_density_min         -0.968
_refine_ls_abs_structure_details
;
Flack parameter determined using 2437 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013).
;
_refine_ls_abs_structure_Flack   0.003(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         7370
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0438P)²+0.8309P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0847
_reflns_number_gt                5962
_reflns_number_total             7370
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yk2170sup1.cif
_cod_data_source_block           I
_cod_database_code               2244117
_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   0.197
_shelx_estimated_absorpt_t_max   0.575
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'
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 0.49964(2) 0.72932(3) 0.49158(6) 0.02765(8) Uani d 1 . .
Br Br2 0.44572(2) 0.50470(2) 0.51189(7) 0.02906(8) Uani d 1 . .
Br Br3 -0.10955(3) 0.24165(3) 0.55241(7) 0.03182(9) Uani d 1 . .
O O1 0.1810(2) 1.1045(2) 0.3729(4) 0.0333(6) Uani d 1 . .
O O2 0.1662(3) 1.1002(2) 0.6323(4) 0.0326(6) Uani d 1 . .
N N1 0.18506(19) 1.0613(2) 0.5020(5) 0.0231(5) Uani d 1 . .
N N2 0.24431(19) 0.57755(19) 0.5188(4) 0.0207(5) Uani d 1 . .
N N3 0.15599(19) 0.5982(2) 0.5376(4) 0.0228(6) Uani d 1 . .
C C1 0.4020(2) 0.6350(2) 0.5012(6) 0.0222(6) Uani d 1 . .
C C2 0.3073(2) 0.6586(2) 0.5080(5) 0.0205(5) Uani d 1 . .
C C3 0.2727(2) 0.7629(2) 0.5040(5) 0.0196(5) Uani d 1 . .
C C4 0.2373(3) 0.8055(3) 0.6449(5) 0.0221(6) Uani d 1 . .
H H4 0.233234 0.767615 0.741062 0.027 Uiso calc 1 . .
C C5 0.2076(3) 0.9043(3) 0.6441(5) 0.0222(6) Uani d 1 . .
H H5 0.184039 0.934772 0.739348 0.027 Uiso calc 1 . .
C C6 0.2136(2) 0.9563(2) 0.5016(5) 0.0212(5) Uani d 1 . .
C C7 0.2468(3) 0.9148(3) 0.3596(5) 0.0249(7) Uani d 1 . .
H H7 0.248972 0.952162 0.262834 0.030 Uiso calc 1 . .
C C8 0.2769(3) 0.8171(3) 0.3629(5) 0.0235(6) Uani d 1 . .
H H8 0.300598 0.787169 0.267351 0.028 Uiso calc 1 . .
C C9 0.0971(2) 0.5110(2) 0.5422(5) 0.0208(6) Uani d 1 . .
C C10 0.0066(3) 0.5207(3) 0.6113(5) 0.0251(7) Uani d 1 . .
H H10 -0.013356 0.582330 0.654399 0.030 Uiso calc 1 . .
C C11 -0.0553(3) 0.4391(3) 0.6172(5) 0.0262(7) Uani d 1 . .
H H11 -0.117165 0.444374 0.665505 0.031 Uiso calc 1 . .
C C12 -0.0249(3) 0.3509(2) 0.5516(5) 0.0243(6) Uani d 1 . .
C C13 0.0662(2) 0.3397(2) 0.4837(5) 0.0246(7) Uani d 1 . .
H H13 0.085933 0.277960 0.440465 0.030 Uiso calc 1 . .
C C14 0.1275(2) 0.4203(2) 0.4803(5) 0.0236(6) Uani d 1 . .
H H14 0.190380 0.413915 0.435972 0.028 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'
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
O1 N1 O2 . . 123.8(3) ?
O1 N1 C6 . . 118.1(3) ?
O2 N1 C6 . . 118.1(3) ?
N3 N2 C2 . . 115.9(3) ?
N2 N3 C9 . . 111.8(3) ?
C2 C1 Br1 . . 123.1(2) ?
C2 C1 Br2 . . 122.4(2) ?
Br1 C1 Br2 . . 114.43(15) ?
C1 C2 N2 . . 115.0(3) ?
C1 C2 C3 . . 122.3(3) ?
N2 C2 C3 . . 122.7(3) ?
C8 C3 C4 . . 120.3(3) ?
C8 C3 C2 . . 120.5(3) ?
C4 C3 C2 . . 119.1(3) ?
C3 C4 C5 . . 119.7(3) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
C6 C5 C4 . . 118.3(3) ?
C6 C5 H5 . . 120.8 ?
C4 C5 H5 . . 120.8 ?
C5 C6 C7 . . 122.9(3) ?
C5 C6 N1 . . 118.3(3) ?
C7 C6 N1 . . 118.8(3) ?
C6 C7 C8 . . 118.0(3) ?
C6 C7 H7 . . 121.0 ?
C8 C7 H7 . . 121.0 ?
C3 C8 C7 . . 120.7(3) ?
C3 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C10 C9 C14 . . 120.6(3) ?
C10 C9 N3 . . 116.6(3) ?
C14 C9 N3 . . 122.8(3) ?
C9 C10 C11 . . 119.7(3) ?
C9 C10 H10 . . 120.2 ?
C11 C10 H10 . . 120.2 ?
C12 C11 C10 . . 118.9(3) ?
C12 C11 H11 . . 120.6 ?
C10 C11 H11 . . 120.6 ?
C11 C12 C13 . . 122.1(3) ?
C11 C12 Br3 . . 119.2(3) ?
C13 C12 Br3 . . 118.7(3) ?
C14 C13 C12 . . 118.7(3) ?
C14 C13 H13 . . 120.7 ?
C12 C13 H13 . . 120.7 ?
C13 C14 C9 . . 120.0(3) ?
C13 C14 H14 . . 120.0 ?
C9 C14 H14 . . 120.0 ?
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 . 1.864(3) ?
Br2 C1 . 1.868(3) ?
Br3 C12 . 1.888(3) ?
O1 N1 . 1.223(5) ?
O2 N1 . 1.231(5) ?
N1 C6 . 1.477(4) ?
N2 N3 . 1.266(4) ?
N2 C2 . 1.406(4) ?
N3 C9 . 1.437(4) ?
C1 C2 . 1.352(4) ?
C2 C3 . 1.492(4) ?
C3 C8 . 1.384(5) ?
C3 C4 . 1.394(5) ?
C4 C5 . 1.400(5) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.379(5) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.384(6) ?
C7 C8 . 1.388(5) ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
C9 C10 . 1.386(5) ?
C9 C14 . 1.397(5) ?
C10 C11 . 1.400(5) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.378(5) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.392(5) ?
C13 C14 . 1.384(5) ?
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
C10 H10 Br1 4_465 0.95 2.89 3.530(4) 126 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 . . . . 178.1(3) ?
Br1 C1 C2 N2 . . . . -178.4(3) ?
Br2 C1 C2 N2 . . . . -1.8(6) ?
Br1 C1 C2 C3 . . . . 1.6(6) ?
Br2 C1 C2 C3 . . . . 178.2(3) ?
N3 N2 C2 C1 . . . . 174.8(4) ?
N3 N2 C2 C3 . . . . -5.2(5) ?
C1 C2 C3 C8 . . . . 72.2(5) ?
N2 C2 C3 C8 . . . . -107.7(4) ?
C1 C2 C3 C4 . . . . -106.9(5) ?
N2 C2 C3 C4 . . . . 73.1(5) ?
C8 C3 C4 C5 . . . . -1.3(5) ?
C2 C3 C4 C5 . . . . 177.8(3) ?
C3 C4 C5 C6 . . . . 0.8(5) ?
C4 C5 C6 C7 . . . . 0.5(5) ?
C4 C5 C6 N1 . . . . -178.2(3) ?
O1 N1 C6 C5 . . . . -172.7(3) ?
O2 N1 C6 C5 . . . . 6.9(4) ?
O1 N1 C6 C7 . . . . 8.6(5) ?
O2 N1 C6 C7 . . . . -171.8(3) ?
C5 C6 C7 C8 . . . . -1.2(5) ?
N1 C6 C7 C8 . . . . 177.5(3) ?
C4 C3 C8 C7 . . . . 0.6(5) ?
C2 C3 C8 C7 . . . . -178.5(3) ?
C6 C7 C8 C3 . . . . 0.6(5) ?
N2 N3 C9 C10 . . . . 160.3(4) ?
N2 N3 C9 C14 . . . . -20.0(5) ?
C14 C9 C10 C11 . . . . -0.9(6) ?
N3 C9 C10 C11 . . . . 178.9(4) ?
C9 C10 C11 C12 . . . . -0.9(6) ?
C10 C11 C12 C13 . . . . 1.7(7) ?
C10 C11 C12 Br3 . . . . -177.8(3) ?
C11 C12 C13 C14 . . . . -0.8(6) ?
Br3 C12 C13 C14 . . . . 178.8(3) ?
C12 C13 C14 C9 . . . . -1.0(6) ?
C10 C9 C14 C13 . . . . 1.8(6) ?
N3 C9 C14 C13 . . . . -177.9(4) ?

_cod_database_fobs_code 2244117
