#------------------------------------------------------------------------------
#$Date: 2023-06-29 18:48:39 +0300 (Thu, 29 Jun 2023) $
#$Revision: 284694 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/27/2022790.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_2022790
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          'C18 H18 Cl2 N2'
_chemical_formula_moiety         'C18 H18 Cl2 N2'
_chemical_formula_sum            'C18 H18 Cl2 N2'
_chemical_formula_weight         333.24
_chemical_name_systematic
(E)-1-[1-(4-tert-Butylphenyl)-2,2-dichloroethenyl]-2-phenyldiazene
_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                 132.669(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   31.7847(8)
_cell_length_b                   6.02890(10)
_cell_length_c                   23.7220(6)
_cell_measurement_reflns_used    12999
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.25
_cell_measurement_theta_min      3.73
_cell_volume                     3342.4(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.992
_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  0.0742
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            25151
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.710
_diffrn_reflns_theta_min         3.743
_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    3.460
_exptl_absorpt_correction_T_max  0.580
_exptl_absorpt_correction_T_min  0.339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       prism
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.355
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3543
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0381
_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)+(0.0617P)²+1.5568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1050
_reflns_number_gt                3242
_reflns_number_total             3543
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5684sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        3342.4(2)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2022790
_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   0.503
_shelx_estimated_absorpt_t_max   0.625
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
C C1 0.41113(6) 0.3707(3) 0.34806(7) 0.0190(3) Uani d 1 . .
C C2 0.44632(6) 0.2439(3) 0.34891(8) 0.0202(3) Uani d 1 . .
C C3 0.40396(6) 0.3436(2) 0.40351(8) 0.0181(3) Uani d 1 . .
C C4 0.42175(6) 0.5130(3) 0.45571(8) 0.0209(3) Uani d 1 . .
H H4 0.439678 0.641238 0.456824 0.025 Uiso calc 1 . .
C C5 0.41349(6) 0.4962(2) 0.50612(8) 0.0202(3) Uani d 1 . .
H H5 0.426029 0.613327 0.541285 0.024 Uiso calc 1 . .
C C6 0.38719(6) 0.3110(2) 0.50615(7) 0.0174(3) Uani d 1 . .
C C7 0.37085(6) 0.1406(3) 0.45491(8) 0.0202(3) Uani d 1 . .
H H7 0.353829 0.010531 0.454639 0.024 Uiso calc 1 . .
C C8 0.37887(6) 0.1563(3) 0.40417(8) 0.0202(3) Uani d 1 . .
H H8 0.367082 0.037981 0.369712 0.024 Uiso calc 1 . .
C C9 0.37725(6) 0.2913(2) 0.56103(8) 0.0190(3) Uani d 1 . .
C C10 0.37583(8) 0.5188(3) 0.58853(10) 0.0298(4) Uani d 1 . .
H H10A 0.413067 0.591510 0.617926 0.045 Uiso calc 1 . .
H H10B 0.367473 0.499800 0.621133 0.045 Uiso calc 1 . .
H H10C 0.346043 0.610581 0.544116 0.045 Uiso calc 1 . .
C C11 0.32022(7) 0.1755(3) 0.52144(9) 0.0276(3) Uani d 1 . .
H H11A 0.289387 0.251751 0.473242 0.041 Uiso calc 1 . .
H H11B 0.312533 0.179721 0.555056 0.041 Uiso calc 1 . .
H H11C 0.322279 0.020866 0.510718 0.041 Uiso calc 1 . .
C C12 0.42652(7) 0.1554(3) 0.63116(9) 0.0290(4) Uani d 1 . .
H H12A 0.427998 0.009439 0.614365 0.044 Uiso calc 1 . .
H H12B 0.420195 0.136703 0.665981 0.044 Uiso calc 1 . .
H H12C 0.462777 0.233242 0.657860 0.044 Uiso calc 1 . .
C C13 0.31598(6) 0.8111(3) 0.23028(8) 0.0190(3) Uani d 1 . .
C C14 0.33920(6) 0.9139(3) 0.20375(8) 0.0223(3) Uani d 1 . .
H H14 0.373214 0.858034 0.217910 0.027 Uiso calc 1 . .
C C15 0.31215(7) 1.0977(3) 0.15666(9) 0.0263(3) Uani d 1 . .
H H15 0.327976 1.169410 0.138947 0.032 Uiso calc 1 . .
C C16 0.26201(7) 1.1785(3) 0.13505(8) 0.0258(3) Uani d 1 . .
H H16 0.243926 1.305662 0.103079 0.031 Uiso calc 1 . .
C C17 0.23826(6) 1.0734(3) 0.16015(8) 0.0260(3) Uani d 1 . .
H H17 0.203476 1.126355 0.144314 0.031 Uiso calc 1 . .
C C18 0.26553(6) 0.8909(3) 0.20839(8) 0.0231(3) Uani d 1 . .
H H18 0.249845 0.820563 0.226471 0.028 Uiso calc 1 . .
Cl Cl1 0.48464(2) 0.02700(6) 0.41131(2) 0.02358(12) Uani d 1 . .
Cl Cl2 0.45673(2) 0.28133(7) 0.28705(2) 0.02385(12) Uani d 1 . .
N N1 0.38241(5) 0.5414(2) 0.29193(7) 0.0193(3) Uani d 1 . .
N N2 0.34302(5) 0.6330(2) 0.28416(6) 0.0199(3) Uani d 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
C2 C1 N1 . . 115.21(13) ?
C2 C1 C3 . . 123.29(13) ?
N1 C1 C3 . . 121.45(13) ?
C1 C2 Cl1 . . 122.94(12) ?
C1 C2 Cl2 . . 123.42(12) ?
Cl1 C2 Cl2 . . 113.64(9) ?
C8 C3 C4 . . 118.41(13) ?
C8 C3 C1 . . 122.15(13) ?
C4 C3 C1 . . 119.42(13) ?
C5 C4 C3 . . 120.69(14) ?
C5 C4 H4 . . 119.7 ?
C3 C4 H4 . . 119.7 ?
C4 C5 C6 . . 121.41(13) ?
C4 C5 H5 . . 119.3 ?
C6 C5 H5 . . 119.3 ?
C5 C6 C7 . . 117.28(13) ?
C5 C6 C9 . . 121.94(13) ?
C7 C6 C9 . . 120.78(13) ?
C8 C7 C6 . . 121.63(14) ?
C8 C7 H7 . . 119.2 ?
C6 C7 H7 . . 119.2 ?
C3 C8 C7 . . 120.55(13) ?
C3 C8 H8 . . 119.7 ?
C7 C8 H8 . . 119.7 ?
C11 C9 C10 . . 107.75(13) ?
C11 C9 C12 . . 109.54(13) ?
C10 C9 C12 . . 108.60(13) ?
C11 C9 C6 . . 110.65(12) ?
C10 C9 C6 . . 111.93(12) ?
C12 C9 C6 . . 108.33(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 . . 120.28(14) ?
C18 C13 N2 . . 115.83(13) ?
C14 C13 N2 . . 123.75(13) ?
C15 C14 C13 . . 119.32(14) ?
C15 C14 H14 . . 120.3 ?
C13 C14 H14 . . 120.3 ?
C14 C15 C16 . . 120.54(15) ?
C14 C15 H15 . . 119.7 ?
C16 C15 H15 . . 119.7 ?
C15 C16 C17 . . 120.12(15) ?
C15 C16 H16 . . 119.9 ?
C17 C16 H16 . . 119.9 ?
C18 C17 C16 . . 119.81(14) ?
C18 C17 H17 . . 120.1 ?
C16 C17 H17 . . 120.1 ?
C17 C18 C13 . . 119.91(14) ?
C17 C18 H18 . . 120.0 ?
C13 C18 H18 . . 120.0 ?
N2 N1 C1 . . 113.43(12) ?
N1 N2 C13 . . 113.31(12) ?
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
C1 C2 . 1.344(2) ?
C1 N1 . 1.4205(19) ?
C1 C3 . 1.4886(19) ?
C2 Cl1 . 1.7146(15) ?
C2 Cl2 . 1.7240(15) ?
C3 C8 . 1.388(2) ?
C3 C4 . 1.396(2) ?
C4 C5 . 1.391(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.395(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.396(2) ?
C6 C9 . 1.5381(19) ?
C7 C8 . 1.393(2) ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
C9 C11 . 1.532(2) ?
C9 C10 . 1.532(2) ?
C9 C12 . 1.536(2) ?
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 . 1.394(2) ?
C13 C14 . 1.398(2) ?
C13 N2 . 1.4269(19) ?
C14 C15 . 1.383(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.390(2) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.391(2) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.388(2) ?
C17 H17 . 0.9500 ?
C18 H18 . 0.9500 ?
N1 N2 . 1.2628(18) ?
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 2.95 3.476(2) 116 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
N1 C1 C2 Cl1 . . . . -179.36(10) ?
C3 C1 C2 Cl1 . . . . 3.2(2) ?
N1 C1 C2 Cl2 . . . . -0.05(19) ?
C3 C1 C2 Cl2 . . . . -177.52(11) ?
C2 C1 C3 C8 . . . . -67.0(2) ?
N1 C1 C3 C8 . . . . 115.67(16) ?
C2 C1 C3 C4 . . . . 114.42(17) ?
N1 C1 C3 C4 . . . . -62.90(18) ?
C8 C3 C4 C5 . . . . -1.2(2) ?
C1 C3 C4 C5 . . . . 177.40(13) ?
C3 C4 C5 C6 . . . . -0.2(2) ?
C4 C5 C6 C7 . . . . 1.7(2) ?
C4 C5 C6 C9 . . . . -179.38(13) ?
C5 C6 C7 C8 . . . . -1.8(2) ?
C9 C6 C7 C8 . . . . 179.25(13) ?
C4 C3 C8 C7 . . . . 1.1(2) ?
C1 C3 C8 C7 . . . . -177.48(13) ?
C6 C7 C8 C3 . . . . 0.4(2) ?
C5 C6 C9 C11 . . . . 143.50(14) ?
C7 C6 C9 C11 . . . . -37.58(18) ?
C5 C6 C9 C10 . . . . 23.30(19) ?
C7 C6 C9 C10 . . . . -157.77(14) ?
C5 C6 C9 C12 . . . . -96.41(16) ?
C7 C6 C9 C12 . . . . 82.52(17) ?
C18 C13 C14 C15 . . . . 1.1(2) ?
N2 C13 C14 C15 . . . . -174.40(14) ?
C13 C14 C15 C16 . . . . -0.8(2) ?
C14 C15 C16 C17 . . . . -0.6(2) ?
C15 C16 C17 C18 . . . . 1.6(2) ?
C16 C17 C18 C13 . . . . -1.3(2) ?
C14 C13 C18 C17 . . . . -0.1(2) ?
N2 C13 C18 C17 . . . . 175.75(13) ?
C2 C1 N1 N2 . . . . 169.00(13) ?
C3 C1 N1 N2 . . . . -13.47(19) ?
C1 N1 N2 C13 . . . . 177.31(11) ?
C18 C13 N2 N1 . . . . 168.30(13) ?
C14 C13 N2 N1 . . . . -16.0(2) ?

_cod_database_fobs_code 2022790
