#------------------------------------------------------------------------------
#$Date: 2023-06-29 18:48:39 +0300 (Thu, 29 Jun 2023) $
#$Revision: 284694 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/27/2022791.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_2022791
loop_
_publ_author_name
'Maharramov, Abel'
'Shikhaliyev, Namiq Q.'
'Qajar, Ayten'
'Atakishiyeva, Gulnar T.'
'Niyazova, Ayten'
'Khrustalev, Victor N.'
'Akkurt, Mehmet'
'Yıldırım, Sema Öztürk'
'Bhattarai, Ajaya'
_publ_section_title
;
 Crystal structures and Hirshfeld surface analyses of
 (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-phenyldiazene,
 (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(4-methylphenyl)diazene,
 (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(4-methoxyphenyl)diazene
 and
 (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(3-methylphenyl)diazene
;
_journal_coeditor_code           WM5684
_journal_issue                   7
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S205698902300511X
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C19 H20 Cl2 N2'
_chemical_formula_moiety         'C19 H20 Cl2 N2'
_chemical_formula_sum            'C19 H20 Cl2 N2'
_chemical_formula_weight         347.27
_chemical_name_systematic
;
(E)-1-[1-(4-tert-Butylphenyl)-2,2-dichloroethenyl]-2-\
(4-methylphenyl)diazene
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 127.223(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.9062(6)
_cell_length_b                   6.27248(5)
_cell_length_c                   23.3475(4)
_cell_measurement_reflns_used    19033
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.14
_cell_measurement_theta_min      3.56
_cell_volume                     3604.08(17)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2021)
;
_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      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            28692
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.530
_diffrn_reflns_theta_min         3.592
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.229
_exptl_absorpt_correction_T_max  0.630
_exptl_absorpt_correction_T_min  0.464
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       prism
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.301
_refine_ls_extinction_coef       0.00017(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2016/6 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0325
_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)+(0.0470P)²+2.8000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0903
_reflns_number_gt                3643
_reflns_number_total             3805
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5684sup1.cif
_cod_data_source_block           II
_cod_original_cell_volume        3604.08(15)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2022791
_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   0.579
_shelx_estimated_absorpt_t_max   0.661
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'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
Cl Cl1 0.48998(2) 0.03552(5) 0.41749(2) 0.02454(11) Uani d 1 . .
Cl Cl2 0.46363(2) 0.25942(5) 0.29246(2) 0.02446(11) Uani d 1 . .
N N1 0.39101(4) 0.51844(18) 0.30369(6) 0.0208(2) Uani d 1 . .
N N2 0.35039(5) 0.59579(18) 0.29674(6) 0.0222(2) Uani d 1 . .
C C1 0.41805(5) 0.3591(2) 0.35785(7) 0.0201(3) Uani d 1 . .
C C2 0.45276(5) 0.2354(2) 0.35637(7) 0.0208(3) Uani d 1 . .
C C3 0.40920(5) 0.3421(2) 0.41360(7) 0.0195(3) Uani d 1 . .
C C4 0.42254(6) 0.5155(2) 0.45907(7) 0.0227(3) Uani d 1 . .
H H4 0.438159 0.639440 0.455003 0.027 Uiso calc 1 . .
C C5 0.41316(6) 0.5082(2) 0.51023(7) 0.0220(3) Uani d 1 . .
H H5 0.422523 0.627803 0.540667 0.026 Uiso calc 1 . .
C C6 0.39028(5) 0.3292(2) 0.51781(7) 0.0191(3) Uani d 1 . .
C C7 0.37776(5) 0.1560(2) 0.47236(7) 0.0211(3) Uani d 1 . .
H H7 0.362819 0.030753 0.477002 0.025 Uiso calc 1 . .
C C8 0.38657(5) 0.1621(2) 0.42057(7) 0.0209(3) Uani d 1 . .
H H8 0.377088 0.042930 0.389929 0.025 Uiso calc 1 . .
C C9 0.38015(5) 0.3145(2) 0.57443(7) 0.0206(3) Uani d 1 . .
C C10 0.38607(6) 0.5300(2) 0.60923(8) 0.0284(3) Uani d 1 . .
H H10A 0.423263 0.582766 0.634072 0.043 Uiso calc 1 . .
H H10B 0.378300 0.513209 0.643923 0.043 Uiso calc 1 . .
H H10C 0.360454 0.632136 0.571982 0.043 Uiso calc 1 . .
C C11 0.32232(6) 0.2333(3) 0.53954(8) 0.0295(3) Uani d 1 . .
H H11A 0.296101 0.325794 0.499032 0.044 Uiso calc 1 . .
H H11B 0.315190 0.234963 0.575128 0.044 Uiso calc 1 . .
H H11C 0.318734 0.087345 0.522185 0.044 Uiso calc 1 . .
C C12 0.42191(6) 0.1599(3) 0.63358(8) 0.0315(3) Uani d 1 . .
H H12A 0.417802 0.019311 0.612496 0.047 Uiso calc 1 . .
H H12B 0.415934 0.147896 0.670170 0.047 Uiso calc 1 . .
H H12C 0.458667 0.213787 0.655851 0.047 Uiso calc 1 . .
C C13 0.32527(5) 0.7652(2) 0.24618(7) 0.0199(3) Uani d 1 . .
C C14 0.35328(5) 0.8930(2) 0.22966(7) 0.0221(3) Uani d 1 . .
H H14 0.390374 0.865296 0.250923 0.027 Uiso calc 1 . .
C C15 0.32646(6) 1.0606(2) 0.18195(8) 0.0252(3) Uani d 1 . .
H H15 0.345643 1.148864 0.171144 0.030 Uiso calc 1 . .
C C16 0.27186(6) 1.1026(2) 0.14946(7) 0.0247(3) Uani d 1 . .
C C17 0.24436(6) 0.9736(2) 0.16630(8) 0.0263(3) Uani d 1 . .
H H17 0.206996 0.999041 0.144008 0.032 Uiso calc 1 . .
C C18 0.27109(6) 0.8078(2) 0.21550(8) 0.0261(3) Uani d 1 . .
H H18 0.252413 0.723936 0.228125 0.031 Uiso calc 1 . .
C C19 0.24335(7) 1.2860(3) 0.09755(9) 0.0361(4) Uani d 1 . .
H H19A 0.204956 1.250175 0.061231 0.054 Uiso calc 1 . .
H H19B 0.260343 1.313112 0.073900 0.054 Uiso calc 1 . .
H H19C 0.246248 1.413799 0.123816 0.054 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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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 C1 . . 112.90(11) ?
N1 N2 C13 . . 113.32(10) ?
C2 C1 N1 . . 115.67(11) ?
C2 C1 C3 . . 123.67(12) ?
N1 C1 C3 . . 120.60(11) ?
C1 C2 Cl1 . . 123.05(10) ?
C1 C2 Cl2 . . 123.35(10) ?
Cl1 C2 Cl2 . . 113.60(7) ?
C8 C3 C4 . . 118.82(12) ?
C8 C3 C1 . . 122.23(12) ?
C4 C3 C1 . . 118.92(11) ?
C5 C4 C3 . . 120.59(12) ?
C5 C4 H4 . . 119.7 ?
C3 C4 H4 . . 119.7 ?
C4 C5 C6 . . 121.38(12) ?
C4 C5 H5 . . 119.3 ?
C6 C5 H5 . . 119.3 ?
C5 C6 C7 . . 117.26(11) ?
C5 C6 C9 . . 122.75(11) ?
C7 C6 C9 . . 119.96(11) ?
C8 C7 C6 . . 121.85(12) ?
C8 C7 H7 . . 119.1 ?
C6 C7 H7 . . 119.1 ?
C3 C8 C7 . . 120.09(12) ?
C3 C8 H8 . . 120.0 ?
C7 C8 H8 . . 120.0 ?
C10 C9 C6 . . 112.52(11) ?
C10 C9 C11 . . 107.56(11) ?
C6 C9 C11 . . 109.98(10) ?
C10 C9 C12 . . 108.35(12) ?
C6 C9 C12 . . 108.31(10) ?
C11 C9 C12 . . 110.09(12) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C9 C11 H11A . . 109.5 ?
C9 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C9 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C9 C12 H12A . . 109.5 ?
C9 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C9 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C18 C13 C14 . . 120.14(12) ?
C18 C13 N2 . . 117.00(12) ?
C14 C13 N2 . . 122.78(12) ?
C15 C14 C13 . . 119.31(12) ?
C15 C14 H14 . . 120.3 ?
C13 C14 H14 . . 120.3 ?
C14 C15 C16 . . 121.31(13) ?
C14 C15 H15 . . 119.3 ?
C16 C15 H15 . . 119.3 ?
C17 C16 C15 . . 118.81(12) ?
C17 C16 C19 . . 120.69(13) ?
C15 C16 C19 . . 120.49(13) ?
C18 C17 C16 . . 120.58(13) ?
C18 C17 H17 . . 119.7 ?
C16 C17 H17 . . 119.7 ?
C17 C18 C13 . . 119.81(13) ?
C17 C18 H18 . . 120.1 ?
C13 C18 H18 . . 120.1 ?
C16 C19 H19A . . 109.5 ?
C16 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C16 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
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 C2 . 1.7163(13) ?
Cl2 C2 . 1.7229(13) ?
N1 N2 . 1.2613(16) ?
N1 C1 . 1.4202(16) ?
N2 C13 . 1.4199(17) ?
C1 C2 . 1.3415(19) ?
C1 C3 . 1.4871(17) ?
C3 C8 . 1.3887(18) ?
C3 C4 . 1.3964(18) ?
C4 C5 . 1.3898(19) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.3942(18) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.3995(18) ?
C6 C9 . 1.5348(17) ?
C7 C8 . 1.3915(18) ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
C9 C10 . 1.5303(18) ?
C9 C11 . 1.5349(18) ?
C9 C12 . 1.5353(19) ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C13 C18 . 1.3921(19) ?
C13 C14 . 1.3944(18) ?
C14 C15 . 1.3844(19) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.394(2) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.391(2) ?
C16 C19 . 1.5089(19) ?
C17 C18 . 1.391(2) ?
C17 H17 . 0.9500 ?
C18 H18 . 0.9500 ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
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
C17 H17 Cg1 4_555 0.95 2.88 3.675(2) 142 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
C1 N1 N2 C13 . . . . 175.97(11) ?
N2 N1 C1 C2 . . . . 164.44(12) ?
N2 N1 C1 C3 . . . . -18.16(17) ?
N1 C1 C2 Cl1 . . . . 179.34(9) ?
C3 C1 C2 Cl1 . . . . 2.03(19) ?
N1 C1 C2 Cl2 . . . . -1.51(18) ?
C3 C1 C2 Cl2 . . . . -178.82(10) ?
C2 C1 C3 C8 . . . . -65.16(18) ?
N1 C1 C3 C8 . . . . 117.65(14) ?
C2 C1 C3 C4 . . . . 116.87(15) ?
N1 C1 C3 C4 . . . . -60.31(17) ?
C8 C3 C4 C5 . . . . -0.2(2) ?
C1 C3 C4 C5 . . . . 177.83(12) ?
C3 C4 C5 C6 . . . . 0.0(2) ?
C4 C5 C6 C7 . . . . 0.74(19) ?
C4 C5 C6 C9 . . . . 179.07(12) ?
C5 C6 C7 C8 . . . . -1.27(19) ?
C9 C6 C7 C8 . . . . -179.65(12) ?
C4 C3 C8 C7 . . . . -0.30(19) ?
C1 C3 C8 C7 . . . . -178.27(12) ?
C6 C7 C8 C3 . . . . 1.1(2) ?
C5 C6 C9 C10 . . . . 12.41(17) ?
C7 C6 C9 C10 . . . . -169.31(12) ?
C5 C6 C9 C11 . . . . 132.31(13) ?
C7 C6 C9 C11 . . . . -49.41(16) ?
C5 C6 C9 C12 . . . . -107.35(14) ?
C7 C6 C9 C12 . . . . 70.94(15) ?
N1 N2 C13 C18 . . . . 157.20(12) ?
N1 N2 C13 C14 . . . . -26.07(18) ?
C18 C13 C14 C15 . . . . -0.7(2) ?
N2 C13 C14 C15 . . . . -177.35(12) ?
C13 C14 C15 C16 . . . . -0.8(2) ?
C14 C15 C16 C17 . . . . 0.7(2) ?
C14 C15 C16 C19 . . . . -179.95(14) ?
C15 C16 C17 C18 . . . . 0.9(2) ?
C19 C16 C17 C18 . . . . -178.43(14) ?
C16 C17 C18 C13 . . . . -2.4(2) ?
C14 C13 C18 C17 . . . . 2.3(2) ?
N2 C13 C18 C17 . . . . 179.13(12) ?

_cod_database_fobs_code 2022791
