#------------------------------------------------------------------------------
#$Date: 2021-02-27 08:00:17 +0200 (Sat, 27 Feb 2021) $
#$Revision: 262299 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/37/2243764.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_2243764
loop_
_publ_author_name
'Temesgen, Ayalew'
'Tskhovrebov, Alexander G.'
'Vologzhanina, Anna V.'
'Le, Tuan A.'
'Khrustalev, Victor N.'
_publ_section_title
;
 Crystal structure of
 2-[(E)-2-(4-bromophenyl)diazen-1-yl]-4,5-bis(4-methoxyphenyl)-1H-imidazole:
 the first example of a structurally characterized triarylazoimidazole
;
_journal_coeditor_code           YK2143
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              305
_journal_page_last               308
_journal_paper_doi               10.1107/S2056989021002024
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C23 H19 Br N4 O2'
_chemical_formula_moiety         'C23 H19 Br N4 O2'
_chemical_formula_sum            'C23 H19 Br N4 O2'
_chemical_formula_weight         463.32
_chemical_name_systematic
2-[(E)-2-(4-Bromophenyl)diazen-1-yl]-4,5-bis(4-methoxyphenyl)-1H-imidazole
_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   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2015
_cell_angle_alpha                90
_cell_angle_beta                 109.635(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7812(9)
_cell_length_b                   12.7877(11)
_cell_length_c                   15.4575(13)
_cell_measurement_reflns_used    2288
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.42
_cell_measurement_theta_min      2.56
_cell_volume                     2007.2(3)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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  0.0839
_diffrn_reflns_av_unetI/netI     0.0893
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22147
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.473
_diffrn_reflns_theta_min         2.006
_exptl_absorpt_coefficient_mu    2.076
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.615
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         6069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0498P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1222
_reflns_number_gt                3449
_reflns_number_total             6069
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yk2143sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243764
_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   0.547
_shelx_estimated_absorpt_t_max   0.851
_shelxl_version_number           .2013
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
Br Br1 0.27445(4) 0.40711(3) -0.14822(2) 0.04431(14) Uani d 1 . .
O O1 -0.01642(18) 0.55364(14) 0.68807(12) 0.0212(4) Uani d 1 . .
O O2 0.84035(18) 0.33604(14) 0.90163(12) 0.0249(4) Uani d 1 . .
N N1 0.2914(2) 0.39235(17) 0.42224(15) 0.0191(5) Uani d 1 . .
H H1 0.222(3) 0.410(2) 0.387(2) 0.023 Uiso d 1 . .
N N2 0.5047(2) 0.35277(17) 0.47136(14) 0.0194(5) Uani d 1 . .
N N3 0.4041(2) 0.36812(17) 0.30966(15) 0.0204(5) Uani d 1 . .
N N4 0.2927(2) 0.38470(16) 0.24827(15) 0.0215(5) Uani d 1 . .
C C1 0.3985(3) 0.36862(19) 0.39831(17) 0.0176(5) Uani d 1 . .
C C2 0.4641(3) 0.37005(19) 0.54552(17) 0.0162(5) Uani d 1 . .
C C3 0.3314(3) 0.39603(19) 0.51634(17) 0.0178(5) Uani d 1 . .
C C4 0.2423(3) 0.43346(19) 0.56408(17) 0.0163(5) Uani d 1 . .
C C5 0.2757(3) 0.5239(2) 0.61663(17) 0.0192(6) Uani d 1 . .
H H5 0.3570 0.5577 0.6235 0.023 Uiso calc 1 . .
C C6 0.1921(3) 0.56603(19) 0.65933(17) 0.0177(6) Uani d 1 . .
H H6 0.2161 0.6281 0.6949 0.021 Uiso calc 1 . .
C C7 0.0742(3) 0.51714(19) 0.64976(17) 0.0175(5) Uani d 1 . .
C C8 0.0393(3) 0.4255(2) 0.59788(18) 0.0203(6) Uani d 1 . .
H H8 -0.0416 0.3915 0.5918 0.024 Uiso calc 1 . .
C C9 0.1230(3) 0.38447(19) 0.55551(17) 0.0190(6) Uani d 1 . .
H H9 0.0990 0.3223 0.5202 0.023 Uiso calc 1 . .
C C10 0.0165(3) 0.6508(2) 0.7369(2) 0.0321(7) Uani d 1 . .
H H10A 0.0296 0.7048 0.6958 0.048 Uiso calc 1 . .
H H10B 0.0978 0.6422 0.7895 0.048 Uiso calc 1 . .
H H10C -0.0552 0.6717 0.7588 0.048 Uiso calc 1 . .
C C11 0.5584(3) 0.36163(19) 0.64007(17) 0.0175(5) Uani d 1 . .
C C12 0.5186(3) 0.34390(19) 0.71556(18) 0.0195(6) Uani d 1 . .
H H12 0.4273 0.3382 0.7065 0.023 Uiso calc 1 . .
C C13 0.6090(3) 0.3342(2) 0.80404(18) 0.0201(6) Uani d 1 . .
H H13 0.5800 0.3203 0.8545 0.024 Uiso calc 1 . .
C C14 0.7421(3) 0.34526(19) 0.81732(17) 0.0199(6) Uani d 1 . .
C C15 0.7843(3) 0.3655(2) 0.74336(18) 0.0208(6) Uani d 1 . .
H H15 0.8753 0.3754 0.7531 0.025 Uiso calc 1 . .
C C16 0.6935(3) 0.3714(2) 0.65562(18) 0.0200(6) Uani d 1 . .
H H16 0.7232 0.3822 0.6050 0.024 Uiso calc 1 . .
C C17 0.7997(3) 0.3123(2) 0.97884(18) 0.0289(7) Uani d 1 . .
H H17A 0.7433 0.2501 0.9652 0.043 Uiso calc 1 . .
H H17B 0.7506 0.3716 0.9911 0.043 Uiso calc 1 . .
H H17C 0.8775 0.2989 1.0329 0.043 Uiso calc 1 . .
C C18 0.2974(3) 0.38963(19) 0.15723(18) 0.0198(6) Uani d 1 . .
C C19 0.4131(3) 0.3895(2) 0.13582(18) 0.0234(6) Uani d 1 . .
H H19 0.4961 0.3872 0.1835 0.028 Uiso calc 1 . .
C C20 0.4069(3) 0.3928(2) 0.04512(19) 0.0270(7) Uani d 1 . .
H H20 0.4851 0.3907 0.0298 0.032 Uiso calc 1 . .
C C21 0.2842(3) 0.3992(2) -0.02354(18) 0.0272(7) Uani d 1 . .
C C22 0.1682(3) 0.4025(2) -0.0033(2) 0.0294(7) Uani d 1 . .
H H22 0.0853 0.4075 -0.0508 0.035 Uiso calc 1 . .
C C23 0.1765(3) 0.3983(2) 0.08831(19) 0.0250(6) Uani d 1 . .
H H23 0.0984 0.4014 0.1037 0.030 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'
Br Br -0.2901 2.4595 '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'
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
C7 O1 C10 . . 115.6(2) ?
C14 O2 C17 . . 116.8(2) ?
C1 N1 C3 . . 107.6(2) ?
C1 N1 H1 . . 125(2) ?
C3 N1 H1 . . 127(2) ?
C1 N2 C2 . . 105.0(2) ?
N4 N3 C1 . . 113.0(2) ?
N3 N4 C18 . . 113.9(2) ?
N2 C1 N1 . . 111.8(2) ?
N2 C1 N3 . . 121.8(2) ?
N1 C1 N3 . . 126.2(2) ?
N2 C2 C3 . . 110.5(2) ?
N2 C2 C11 . . 120.5(2) ?
C3 C2 C11 . . 129.1(2) ?
N1 C3 C2 . . 105.0(2) ?
N1 C3 C4 . . 121.1(2) ?
C2 C3 C4 . . 133.5(2) ?
C5 C4 C9 . . 118.6(2) ?
C5 C4 C3 . . 118.6(2) ?
C9 C4 C3 . . 122.8(2) ?
C4 C5 C6 . . 121.2(3) ?
C4 C5 H5 . . 119.4 ?
C6 C5 H5 . . 119.4 ?
C7 C6 C5 . . 119.6(2) ?
C7 C6 H6 . . 120.2 ?
C5 C6 H6 . . 120.2 ?
C6 C7 O1 . . 124.0(2) ?
C6 C7 C8 . . 120.1(2) ?
O1 C7 C8 . . 115.9(2) ?
C9 C8 C7 . . 119.8(2) ?
C9 C8 H8 . . 120.1 ?
C7 C8 H8 . . 120.1 ?
C8 C9 C4 . . 120.8(2) ?
C8 C9 H9 . . 119.6 ?
C4 C9 H9 . . 119.6 ?
O1 C10 H10A . . 109.5 ?
O1 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
O1 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C12 C11 C16 . . 117.8(2) ?
C12 C11 C2 . . 122.6(2) ?
C16 C11 C2 . . 119.6(2) ?
C11 C12 C13 . . 121.8(3) ?
C11 C12 H12 . . 119.1 ?
C13 C12 H12 . . 119.1 ?
C14 C13 C12 . . 119.0(2) ?
C14 C13 H13 . . 120.5 ?
C12 C13 H13 . . 120.5 ?
O2 C14 C13 . . 123.9(2) ?
O2 C14 C15 . . 115.7(2) ?
C13 C14 C15 . . 120.4(2) ?
C16 C15 C14 . . 119.9(3) ?
C16 C15 H15 . . 120.1 ?
C14 C15 H15 . . 120.1 ?
C15 C16 C11 . . 121.1(2) ?
C15 C16 H16 . . 119.4 ?
C11 C16 H16 . . 119.4 ?
O2 C17 H17A . . 109.5 ?
O2 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O2 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C23 C18 C19 . . 120.3(2) ?
C23 C18 N4 . . 115.2(2) ?
C19 C18 N4 . . 124.4(2) ?
C20 C19 C18 . . 119.9(3) ?
C20 C19 H19 . . 120.0 ?
C18 C19 H19 . . 120.0 ?
C19 C20 C21 . . 119.0(3) ?
C19 C20 H20 . . 120.5 ?
C21 C20 H20 . . 120.5 ?
C22 C21 C20 . . 121.8(3) ?
C22 C21 Br1 . . 118.8(2) ?
C20 C21 Br1 . . 119.4(2) ?
C21 C22 C23 . . 118.3(3) ?
C21 C22 H22 . . 120.8 ?
C23 C22 H22 . . 120.8 ?
C18 C23 C22 . . 120.6(3) ?
C18 C23 H23 . . 119.7 ?
C22 C23 H23 . . 119.7 ?
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 C21 . 1.897(3) ?
O1 C7 . 1.382(3) ?
O1 C10 . 1.435(3) ?
O2 C14 . 1.381(3) ?
O2 C17 . 1.435(3) ?
N1 C1 . 1.360(3) ?
N1 C3 . 1.372(3) ?
N1 H1 . 0.80(3) ?
N2 C1 . 1.326(3) ?
N2 C2 . 1.375(3) ?
N3 N4 . 1.274(3) ?
N3 C1 . 1.392(3) ?
N4 C18 . 1.427(3) ?
C2 C3 . 1.388(4) ?
C2 C11 . 1.477(4) ?
C3 C4 . 1.474(4) ?
C4 C5 . 1.390(3) ?
C4 C9 . 1.397(4) ?
C5 C6 . 1.392(4) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.379(4) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.399(3) ?
C8 C9 . 1.384(4) ?
C8 H8 . 0.9500 ?
C9 H9 . 0.9500 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 C12 . 1.390(4) ?
C11 C16 . 1.400(4) ?
C12 C13 . 1.393(4) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.387(4) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.389(4) ?
C15 C16 . 1.382(4) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C18 C23 . 1.383(4) ?
C18 C19 . 1.393(4) ?
C19 C20 . 1.382(4) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.392(4) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.388(5) ?
C22 C23 . 1.389(4) ?
C22 H22 . 0.9500 ?
C23 H23 . 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
N1 H1 O1 3_566 0.80(3) 2.17(3) 2.963(3) 169(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
C1 N3 N4 C18 . . . . 177.1(2) ?
C2 N2 C1 N1 . . . . -1.7(3) ?
C2 N2 C1 N3 . . . . 173.7(2) ?
C3 N1 C1 N2 . . . . 2.4(3) ?
C3 N1 C1 N3 . . . . -172.7(2) ?
N4 N3 C1 N2 . . . . 180.0(2) ?
N4 N3 C1 N1 . . . . -5.3(4) ?
C1 N2 C2 C3 . . . . 0.4(3) ?
C1 N2 C2 C11 . . . . -178.7(2) ?
C1 N1 C3 C2 . . . . -2.0(3) ?
C1 N1 C3 C4 . . . . 171.9(2) ?
N2 C2 C3 N1 . . . . 1.0(3) ?
C11 C2 C3 N1 . . . . 180.0(2) ?
N2 C2 C3 C4 . . . . -171.7(3) ?
C11 C2 C3 C4 . . . . 7.2(5) ?
N1 C3 C4 C5 . . . . -115.9(3) ?
C2 C3 C4 C5 . . . . 55.9(4) ?
N1 C3 C4 C9 . . . . 61.2(3) ?
C2 C3 C4 C9 . . . . -127.0(3) ?
C9 C4 C5 C6 . . . . -0.6(4) ?
C3 C4 C5 C6 . . . . 176.6(2) ?
C4 C5 C6 C7 . . . . 0.2(4) ?
C5 C6 C7 O1 . . . . -178.9(2) ?
C5 C6 C7 C8 . . . . 0.4(4) ?
C10 O1 C7 C6 . . . . 2.6(4) ?
C10 O1 C7 C8 . . . . -176.7(2) ?
C6 C7 C8 C9 . . . . -0.6(4) ?
O1 C7 C8 C9 . . . . 178.7(2) ?
C7 C8 C9 C4 . . . . 0.1(4) ?
C5 C4 C9 C8 . . . . 0.4(4) ?
C3 C4 C9 C8 . . . . -176.7(2) ?
N2 C2 C11 C12 . . . . -158.2(2) ?
C3 C2 C11 C12 . . . . 22.9(4) ?
N2 C2 C11 C16 . . . . 21.6(3) ?
C3 C2 C11 C16 . . . . -157.2(3) ?
C16 C11 C12 C13 . . . . -1.1(4) ?
C2 C11 C12 C13 . . . . 178.8(2) ?
C11 C12 C13 C14 . . . . 1.7(4) ?
C17 O2 C14 C13 . . . . 0.8(4) ?
C17 O2 C14 C15 . . . . -178.4(2) ?
C12 C13 C14 O2 . . . . -179.2(2) ?
C12 C13 C14 C15 . . . . -0.1(4) ?
O2 C14 C15 C16 . . . . 177.1(2) ?
C13 C14 C15 C16 . . . . -2.1(4) ?
C14 C15 C16 C11 . . . . 2.7(4) ?
C12 C11 C16 C15 . . . . -1.2(4) ?
C2 C11 C16 C15 . . . . 179.0(2) ?
N3 N4 C18 C23 . . . . 174.5(2) ?
N3 N4 C18 C19 . . . . -7.5(4) ?
C23 C18 C19 C20 . . . . -3.2(4) ?
N4 C18 C19 C20 . . . . 178.9(2) ?
C18 C19 C20 C21 . . . . 1.8(4) ?
C19 C20 C21 C22 . . . . 0.1(4) ?
C19 C20 C21 Br1 . . . . 178.5(2) ?
C20 C21 C22 C23 . . . . -0.6(4) ?
Br1 C21 C22 C23 . . . . -179.0(2) ?
C19 C18 C23 C22 . . . . 2.8(4) ?
N4 C18 C23 C22 . . . . -179.2(2) ?
C21 C22 C23 C18 . . . . -0.8(4) ?

_cod_database_fobs_code 2243764
