#------------------------------------------------------------------------------
#$Date: 2021-07-21 08:23:15 +0300 (Wed, 21 Jul 2021) $
#$Revision: 267667 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/38/2243873.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_2243873
loop_
_publ_author_name
'Shikhaliyev, Namiq Q.'
'Atioğlu, Zeliha'
'Akkurt, Mehmet'
'Ahmadova, Nigar E.'
'Askerov, Rizvan K.'
'Bhattarai, Ajaya'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 1,3-bis{2,2-dichloro-1-[(E)-phenyldiazenyl]ethenyl}benzene
;
_journal_coeditor_code           YK2154
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              814
_journal_page_last               818
_journal_paper_doi               10.1107/S2056989021007192
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C22 H14 Cl4 N4'
_chemical_formula_moiety         'C22 H14 Cl4 N4'
_chemical_formula_sum            'C22 H14 Cl4 N4'
_chemical_formula_weight         476.17
_chemical_name_common
;
1,3-Bis{2,2-dichloro-1-[(E)-phenyldiazenyl]ethenyl}benzene
;
_chemical_name_systematic
(E)-[2,2-Dichloro-1-(3-{2,2-dichloro-1-[(E)-2-phenyldiazen-1-yl]ethenyl}phenyl)ethenyl](phenyl)diazene
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 108.073(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0289(10)
_cell_length_b                   13.1213(8)
_cell_length_c                   11.1286(7)
_cell_measurement_reflns_used    6439
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.51
_cell_volume                     2225.1(2)
_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, 2020)
;
_computing_structure_refinement
;
SHELXL2016/6 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2016/6 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24362
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.408
_diffrn_reflns_theta_min         2.048
_exptl_absorpt_coefficient_mu    0.549
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       prism
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.435
_exptl_crystal_size_mid          0.262
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.250
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0456P)²+1.0697P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1117
_reflns_number_gt                3193
_reflns_number_total             4399
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yk2154sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243873
_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   0.796
_shelx_estimated_absorpt_t_max   0.936
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'
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
Cl Cl1 0.74226(5) 0.14141(5) -0.10025(7) 0.0592(2) Uani d 1 . .
Cl Cl2 0.81687(6) 0.33515(7) -0.12359(8) 0.0777(3) Uani d 1 . .
Cl Cl3 0.97228(5) 0.57996(7) 0.11006(7) 0.0736(3) Uani d 1 . .
Cl Cl4 1.05825(5) 0.63410(7) 0.36813(8) 0.0762(3) Uani d 1 . .
N N1 0.65092(13) 0.24501(16) 0.05084(19) 0.0467(5) Uani d 1 . .
N N2 0.60887(13) 0.28678(16) 0.11510(19) 0.0488(5) Uani d 1 . .
N N3 0.88872(14) 0.60214(16) 0.40656(19) 0.0469(5) Uani d 1 . .
N N4 0.81623(14) 0.58883(16) 0.42594(18) 0.0468(5) Uani d 1 . .
C C1 0.74926(16) 0.2676(2) -0.0611(2) 0.0472(6) Uani d 1 . .
C C2 0.70658(15) 0.31073(19) 0.0111(2) 0.0435(6) Uani d 1 . .
C C3 0.55342(16) 0.2175(2) 0.1536(2) 0.0480(6) Uani d 1 . .
C C4 0.5054(2) 0.2569(3) 0.2249(3) 0.0698(8) Uani d 1 . .
H H4A 0.510609 0.325648 0.246399 0.084 Uiso calc 1 . .
C C5 0.4494(2) 0.1959(3) 0.2652(3) 0.0830(10) Uani d 1 . .
H H5A 0.417287 0.223700 0.313982 0.100 Uiso calc 1 . .
C C6 0.44075(19) 0.0957(3) 0.2343(3) 0.0721(9) Uani d 1 . .
H H6A 0.402268 0.054889 0.260581 0.086 Uiso calc 1 . .
C C7 0.4887(2) 0.0553(3) 0.1645(3) 0.0730(9) Uani d 1 . .
H H7A 0.483059 -0.013532 0.143736 0.088 Uiso calc 1 . .
C C8 0.5458(2) 0.1151(2) 0.1240(3) 0.0641(8) Uani d 1 . .
H H8A 0.578832 0.086471 0.077119 0.077 Uiso calc 1 . .
C C9 0.71822(15) 0.41985(18) 0.0494(2) 0.0419(5) Uani d 1 . .
C C10 0.79331(15) 0.45017(18) 0.1441(2) 0.0409(5) Uani d 1 . .
H H10A 0.835438 0.401942 0.183488 0.049 Uiso calc 1 . .
C C11 0.80614(15) 0.55110(18) 0.1805(2) 0.0386(5) Uani d 1 . .
C C12 0.74374(16) 0.62289(19) 0.1206(2) 0.0465(6) Uani d 1 . .
H H12A 0.751924 0.691101 0.144018 0.056 Uiso calc 1 . .
C C13 0.66925(17) 0.5928(2) 0.0259(2) 0.0545(7) Uani d 1 . .
H H13A 0.627449 0.641110 -0.014303 0.065 Uiso calc 1 . .
C C14 0.65639(16) 0.4924(2) -0.0093(2) 0.0510(6) Uani d 1 . .
H H14A 0.605927 0.472971 -0.072944 0.061 Uiso calc 1 . .
C C15 0.96300(16) 0.5965(2) 0.2578(2) 0.0498(6) Uani d 1 . .
C C16 0.88676(15) 0.58312(18) 0.2816(2) 0.0418(5) Uani d 1 . .
C C17 0.82000(18) 0.60524(19) 0.5545(2) 0.0477(6) Uani d 1 . .
C C18 0.89313(19) 0.6384(2) 0.6491(2) 0.0571(7) Uani d 1 . .
H H18A 0.944637 0.653856 0.631148 0.068 Uiso calc 1 . .
C C19 0.8890(2) 0.6485(2) 0.7705(3) 0.0670(8) Uani d 1 . .
H H19A 0.938099 0.670842 0.834584 0.080 Uiso calc 1 . .
C C20 0.8130(3) 0.6258(2) 0.7979(3) 0.0717(9) Uani d 1 . .
H H20A 0.810894 0.632115 0.880182 0.086 Uiso calc 1 . .
C C21 0.7409(2) 0.5940(2) 0.7040(3) 0.0699(8) Uani d 1 . .
H H21A 0.689496 0.578686 0.722387 0.084 Uiso calc 1 . .
C C22 0.74340(19) 0.5843(2) 0.5820(3) 0.0589(7) Uani d 1 . .
H H22A 0.693555 0.563666 0.518131 0.071 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'
Cl Cl 0.1484 0.1585 '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
N2 N1 C2 . . 114.7(2) ?
N1 N2 C3 . . 112.9(2) ?
N4 N3 C16 . . 114.0(2) ?
N3 N4 C17 . . 113.3(2) ?
C2 C1 Cl2 . . 122.4(2) ?
C2 C1 Cl1 . . 124.1(2) ?
Cl2 C1 Cl1 . . 113.55(15) ?
C1 C2 N1 . . 115.1(2) ?
C1 C2 C9 . . 122.6(2) ?
N1 C2 C9 . . 122.3(2) ?
C4 C3 C8 . . 118.9(3) ?
C4 C3 N2 . . 116.6(3) ?
C8 C3 N2 . . 124.5(2) ?
C3 C4 C5 . . 120.7(3) ?
C3 C4 H4A . . 119.7 ?
C5 C4 H4A . . 119.7 ?
C6 C5 C4 . . 120.4(3) ?
C6 C5 H5A . . 119.8 ?
C4 C5 H5A . . 119.8 ?
C5 C6 C7 . . 119.5(3) ?
C5 C6 H6A . . 120.2 ?
C7 C6 H6A . . 120.2 ?
C6 C7 C8 . . 121.0(3) ?
C6 C7 H7A . . 119.5 ?
C8 C7 H7A . . 119.5 ?
C3 C8 C7 . . 119.5(3) ?
C3 C8 H8A . . 120.2 ?
C7 C8 H8A . . 120.2 ?
C14 C9 C10 . . 119.1(2) ?
C14 C9 C2 . . 121.2(2) ?
C10 C9 C2 . . 119.6(2) ?
C11 C10 C9 . . 120.8(2) ?
C11 C10 H10A . . 119.6 ?
C9 C10 H10A . . 119.6 ?
C10 C11 C12 . . 119.4(2) ?
C10 C11 C16 . . 120.5(2) ?
C12 C11 C16 . . 120.0(2) ?
C13 C12 C11 . . 119.8(2) ?
C13 C12 H12A . . 120.1 ?
C11 C12 H12A . . 120.1 ?
C14 C13 C12 . . 120.6(2) ?
C14 C13 H13A . . 119.7 ?
C12 C13 H13A . . 119.7 ?
C13 C14 C9 . . 120.2(2) ?
C13 C14 H14A . . 119.9 ?
C9 C14 H14A . . 119.9 ?
C16 C15 Cl4 . . 124.2(2) ?
C16 C15 Cl3 . . 122.0(2) ?
Cl4 C15 Cl3 . . 113.76(15) ?
C15 C16 N3 . . 115.6(2) ?
C15 C16 C11 . . 121.3(2) ?
N3 C16 C11 . . 123.2(2) ?
C18 C17 C22 . . 119.7(3) ?
C18 C17 N4 . . 125.0(3) ?
C22 C17 N4 . . 115.3(2) ?
C19 C18 C17 . . 119.3(3) ?
C19 C18 H18A . . 120.3 ?
C17 C18 H18A . . 120.3 ?
C20 C19 C18 . . 120.7(3) ?
C20 C19 H19A . . 119.7 ?
C18 C19 H19A . . 119.7 ?
C21 C20 C19 . . 119.7(3) ?
C21 C20 H20A . . 120.2 ?
C19 C20 H20A . . 120.2 ?
C20 C21 C22 . . 120.5(3) ?
C20 C21 H21A . . 119.7 ?
C22 C21 H21A . . 119.7 ?
C21 C22 C17 . . 120.0(3) ?
C21 C22 H22A . . 120.0 ?
C17 C22 H22A . . 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
Cl1 C1 . 1.707(3) ?
Cl2 C1 . 1.706(3) ?
Cl3 C15 . 1.710(3) ?
Cl4 C15 . 1.709(2) ?
N1 N2 . 1.251(3) ?
N1 C2 . 1.407(3) ?
N2 C3 . 1.427(3) ?
N3 N4 . 1.258(3) ?
N3 C16 . 1.404(3) ?
N4 C17 . 1.430(3) ?
C1 C2 . 1.333(3) ?
C2 C9 . 1.489(3) ?
C3 C4 . 1.367(4) ?
C3 C8 . 1.380(4) ?
C4 C5 . 1.378(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.356(5) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.358(4) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.383(4) ?
C7 H7A . 0.9300 ?
C8 H8A . 0.9300 ?
C9 C14 . 1.383(3) ?
C9 C10 . 1.389(3) ?
C10 C11 . 1.381(3) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.385(3) ?
C11 C16 . 1.487(3) ?
C12 C13 . 1.383(3) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.372(4) ?
C13 H13A . 0.9300 ?
C14 H14A . 0.9300 ?
C15 C16 . 1.340(3) ?
C17 C18 . 1.381(4) ?
C17 C22 . 1.382(4) ?
C18 C19 . 1.380(4) ?
C18 H18A . 0.9300 ?
C19 C20 . 1.378(4) ?
C19 H19A . 0.9300 ?
C20 C21 . 1.361(4) ?
C20 H20A . 0.9300 ?
C21 C22 . 1.376(4) ?
C21 H21A . 0.9300 ?
C22 H22A . 0.9300 ?
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
C12 H12A Cg3 4_575 0.93 2.72 3.610(3) 162 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 N1 N2 C3 . . . . -179.88(19) ?
C16 N3 N4 C17 . . . . 178.1(2) ?
Cl1 C1 C2 N1 . . . . -2.4(3) ?
Cl2 C1 C2 C9 . . . . -3.6(3) ?
Cl1 C1 C2 C9 . . . . 176.39(18) ?
N2 N1 C2 C1 . . . . -177.7(2) ?
N2 N1 C2 C9 . . . . 3.5(3) ?
N1 N2 C3 C4 . . . . 179.7(2) ?
N1 N2 C3 C8 . . . . -0.1(4) ?
C8 C3 C4 C5 . . . . -0.9(5) ?
N2 C3 C4 C5 . . . . 179.3(3) ?
C3 C4 C5 C6 . . . . -0.3(5) ?
C4 C5 C6 C7 . . . . 0.9(5) ?
C5 C6 C7 C8 . . . . -0.4(5) ?
C4 C3 C8 C7 . . . . 1.4(4) ?
N2 C3 C8 C7 . . . . -178.8(3) ?
C6 C7 C8 C3 . . . . -0.7(5) ?
C1 C2 C9 C14 . . . . 102.4(3) ?
N1 C2 C9 C14 . . . . -79.0(3) ?
C1 C2 C9 C10 . . . . -76.3(3) ?
N1 C2 C9 C10 . . . . 102.4(3) ?
C14 C9 C10 C11 . . . . 0.6(3) ?
C2 C9 C10 C11 . . . . 179.3(2) ?
C9 C10 C11 C12 . . . . -0.8(3) ?
C9 C10 C11 C16 . . . . -179.8(2) ?
C10 C11 C12 C13 . . . . 0.4(4) ?
C16 C11 C12 C13 . . . . 179.5(2) ?
C11 C12 C13 C14 . . . . 0.1(4) ?
C12 C13 C14 C9 . . . . -0.2(4) ?
C10 C9 C14 C13 . . . . -0.1(4) ?
C2 C9 C14 C13 . . . . -178.8(2) ?
Cl4 C15 C16 N3 . . . . 0.0(3) ?
Cl3 C15 C16 N3 . . . . -178.32(18) ?
Cl4 C15 C16 C11 . . . . 179.46(19) ?
Cl3 C15 C16 C11 . . . . 1.2(4) ?
N4 N3 C16 C15 . . . . -179.9(2) ?
N4 N3 C16 C11 . . . . 0.6(3) ?
C10 C11 C16 C15 . . . . 79.5(3) ?
C12 C11 C16 C15 . . . . -99.6(3) ?
C10 C11 C16 N3 . . . . -101.1(3) ?
C12 C11 C16 N3 . . . . 79.9(3) ?
N3 N4 C17 C18 . . . . 3.8(4) ?
N3 N4 C17 C22 . . . . -175.5(2) ?
C22 C17 C18 C19 . . . . 1.1(4) ?
N4 C17 C18 C19 . . . . -178.1(2) ?
C17 C18 C19 C20 . . . . 0.0(4) ?
C18 C19 C20 C21 . . . . -0.6(5) ?
C19 C20 C21 C22 . . . . 0.1(5) ?
C20 C21 C22 C17 . . . . 1.1(5) ?
C18 C17 C22 C21 . . . . -1.7(4) ?
N4 C17 C22 C21 . . . . 177.6(3) ?

_cod_database_fobs_code 2243873
