#------------------------------------------------------------------------------
#$Date: 2024-03-05 22:28:40 +0200 (Tue, 05 Mar 2024) $
#$Revision: 290318 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/24/2312413.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_2312413
loop_
_publ_author_name
'Shikhaliyev, Namiq Q.'
'İbrahimova, Shafiga A'
'Atakishiyeva, Gulnar T.'
'Ahmedova, Nigar E.'
'Babayeva, Gulnara V.'
'Khrustalev, Victor N.'
'Atioğlu, Zeliha'
'Akkurt, Mehmet'
'Bhattarai, Ajaya'
_publ_section_title
;
 Crystal structures and Hirshfeld surface analyses of methyl
 4-{2,2-di-chloro-1-[(E)-phenyl-diazen-yl]eth-enyl}benzoate, methyl
 4-{2,2-di-chloro-1-[(E)-(4-methyl-phen-yl)diazen-yl]ethen-yl}benzoate
 and methyl
 4-{2,2-di-chloro-1-[(E)-(3,4-di-methyl-phen-yl)diazen-yl]ethen-yl}benzoate.
;
_journal_coeditor_code           WM5708
_journal_issue                   'Pt 2'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              184
_journal_page_last               190
_journal_paper_doi               10.1107/S2056989024000732
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C18 H16 Cl2 N2 O2'
_chemical_formula_moiety         'C18 H16 Cl2 N2 O2'
_chemical_formula_sum            'C18 H16 Cl2 N2 O2'
_chemical_formula_weight         363.23
_chemical_name_systematic
;
Methyl
4-{2,2-dichloro-1-[(E)-(3,4-dimethylphenyl)diazenyl]ethenyl}benzoate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                103.9484(9)
_cell_angle_beta                 101.9047(10)
_cell_angle_gamma                98.0600(9)
_cell_formula_units_Z            2
_cell_length_a                   8.22057(10)
_cell_length_b                   8.53211(9)
_cell_length_c                   13.08729(14)
_cell_measurement_reflns_used    14210
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.96
_cell_measurement_theta_min      3.58
_cell_volume                     854.086(18)
_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
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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  0.0629
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29808
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.802
_diffrn_reflns_theta_min         3.594
_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    3.527
_exptl_absorpt_correction_T_max  0.700
_exptl_absorpt_correction_T_min  0.349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.460
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3632
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0348
_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)+(0.0537P)²+0.2636P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.0974
_reflns_number_gt                3340
_reflns_number_total             3632
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5708.cif
_cod_data_source_block           III
_cod_original_cell_volume        854.086(17)
_cod_database_code               2312413
_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   0.539
_shelx_estimated_absorpt_t_max   0.742
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
Cl Cl1 0.07283(5) -0.14861(4) 0.77715(3) 0.02444(11) Uani d 1 . .
Cl Cl2 0.13915(5) -0.31047(4) 0.57534(3) 0.02637(12) Uani d 1 . .
O O1 0.30977(14) 0.68544(14) 1.04185(9) 0.0315(3) Uani d 1 . .
O O2 0.04043(13) 0.67433(12) 0.95696(8) 0.0208(2) Uani d 1 . .
N N1 0.21612(15) 0.01951(15) 0.54534(10) 0.0198(2) Uani d 1 . .
N N2 0.26094(15) 0.16265(15) 0.53648(10) 0.0208(3) Uani d 1 . .
C C1 0.17177(17) 0.02110(17) 0.64440(11) 0.0189(3) Uani d 1 . .
C C2 0.13347(18) -0.12681(18) 0.66254(11) 0.0206(3) Uani d 1 . .
C C3 0.17331(18) 0.17742(17) 0.72590(11) 0.0185(3) Uani d 1 . .
C C4 0.05481(18) 0.27494(17) 0.70373(11) 0.0203(3) Uani d 1 . .
H H4 -0.026457 0.242988 0.635554 0.024 Uiso calc 1 . .
C C5 0.05592(18) 0.41897(17) 0.78162(12) 0.0203(3) Uani d 1 . .
H H5 -0.026072 0.484181 0.767260 0.024 Uiso calc 1 . .
C C6 0.17767(17) 0.46736(17) 0.88079(11) 0.0188(3) Uani d 1 . .
C C7 0.29835(18) 0.37242(17) 0.90121(11) 0.0202(3) Uani d 1 . .
H H7 0.382930 0.406872 0.968032 0.024 Uiso calc 1 . .
C C8 0.29570(18) 0.22742(17) 0.82428(12) 0.0202(3) Uani d 1 . .
H H8 0.377651 0.162276 0.838900 0.024 Uiso calc 1 . .
C C9 0.18624(18) 0.61892(17) 0.96841(12) 0.0209(3) Uani d 1 . .
C C10 0.0464(2) 0.82424(18) 1.03931(12) 0.0244(3) Uani d 1 . .
H H10A -0.063270 0.858160 1.025427 0.037 Uiso calc 1 . .
H H10B 0.135720 0.911518 1.037093 0.037 Uiso calc 1 . .
H H10C 0.070772 0.804528 1.111150 0.037 Uiso calc 1 . .
C C11 0.31099(18) 0.16259(18) 0.43840(11) 0.0207(3) Uani d 1 . .
C C12 0.33518(19) 0.31514(18) 0.41637(12) 0.0232(3) Uani d 1 . .
H H12 0.318547 0.409355 0.466000 0.028 Uiso calc 1 . .
C C13 0.38330(18) 0.3316(2) 0.32285(13) 0.0249(3) Uani d 1 . .
C C14 0.40929(18) 0.1914(2) 0.25099(12) 0.0258(3) Uani d 1 . .
C C15 0.38626(19) 0.0399(2) 0.27461(12) 0.0260(3) Uani d 1 . .
H H15 0.403729 -0.054527 0.225581 0.031 Uiso calc 1 . .
C C16 0.33864(19) 0.02371(19) 0.36759(12) 0.0231(3) Uani d 1 . .
H H16 0.325038 -0.079976 0.382923 0.028 Uiso calc 1 . .
C C17 0.4088(2) 0.4974(2) 0.30023(15) 0.0333(4) Uani d 1 . .
H H17A 0.376239 0.578206 0.355458 0.050 Uiso calc 1 . .
H H17B 0.338263 0.488834 0.228149 0.050 Uiso calc 1 . .
H H17C 0.528407 0.532926 0.302386 0.050 Uiso calc 1 . .
C C18 0.4627(2) 0.2029(3) 0.14898(14) 0.0363(4) Uani d 1 . .
H H18A 0.377011 0.242730 0.103353 0.055 Uiso calc 1 . .
H H18B 0.473909 0.093688 0.108817 0.055 Uiso calc 1 . .
H H18C 0.571996 0.279612 0.168542 0.055 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'
O O 0.0492 0.0322 '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
C9 O2 C10 . . 113.91(11) ?
N2 N1 C1 . . 112.85(11) ?
N1 N2 C11 . . 113.33(12) ?
C2 C1 N1 . . 116.08(12) ?
C2 C1 C3 . . 121.77(12) ?
N1 C1 C3 . . 122.12(12) ?
C1 C2 Cl2 . . 124.19(11) ?
C1 C2 Cl1 . . 122.44(11) ?
Cl2 C2 Cl1 . . 113.37(8) ?
C8 C3 C4 . . 119.86(13) ?
C8 C3 C1 . . 119.43(13) ?
C4 C3 C1 . . 120.70(13) ?
C5 C4 C3 . . 119.96(13) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 119.88(13) ?
C4 C5 H5 . . 120.1 ?
C6 C5 H5 . . 120.1 ?
C7 C6 C5 . . 119.93(13) ?
C7 C6 C9 . . 117.03(13) ?
C5 C6 C9 . . 123.04(13) ?
C8 C7 C6 . . 120.22(13) ?
C8 C7 H7 . . 119.9 ?
C6 C7 H7 . . 119.9 ?
C7 C8 C3 . . 120.10(13) ?
C7 C8 H8 . . 119.9 ?
C3 C8 H8 . . 119.9 ?
O1 C9 O2 . . 123.20(13) ?
O1 C9 C6 . . 124.17(13) ?
O2 C9 C6 . . 112.64(12) ?
O2 C10 H10A . . 109.5 ?
O2 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
O2 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C16 C11 C12 . . 120.15(13) ?
C16 C11 N2 . . 124.38(13) ?
C12 C11 N2 . . 115.46(13) ?
C13 C12 C11 . . 121.13(14) ?
C13 C12 H12 . . 119.4 ?
C11 C12 H12 . . 119.4 ?
C12 C13 C14 . . 118.70(14) ?
C12 C13 C17 . . 120.45(15) ?
C14 C13 C17 . . 120.84(14) ?
C15 C14 C13 . . 119.55(13) ?
C15 C14 C18 . . 119.66(15) ?
C13 C14 C18 . . 120.80(15) ?
C16 C15 C14 . . 121.71(14) ?
C16 C15 H15 . . 119.1 ?
C14 C15 H15 . . 119.1 ?
C15 C16 C11 . . 118.75(14) ?
C15 C16 H16 . . 120.6 ?
C11 C16 H16 . . 120.6 ?
C13 C17 H17A . . 109.5 ?
C13 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C13 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C14 C18 H18A . . 109.5 ?
C14 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C14 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 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 . 1.7176(14) ?
Cl2 C2 . 1.7148(14) ?
O1 C9 . 1.2041(19) ?
O2 C9 . 1.3422(17) ?
O2 C10 . 1.4478(17) ?
N1 N2 . 1.2651(17) ?
N1 C1 . 1.4148(17) ?
N2 C11 . 1.4263(17) ?
C1 C2 . 1.346(2) ?
C1 C3 . 1.4901(19) ?
C3 C8 . 1.390(2) ?
C3 C4 . 1.397(2) ?
C4 C5 . 1.392(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.395(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.390(2) ?
C6 C9 . 1.4894(19) ?
C7 C8 . 1.388(2) ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 C16 . 1.396(2) ?
C11 C12 . 1.396(2) ?
C12 C13 . 1.393(2) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.404(2) ?
C13 C17 . 1.509(2) ?
C14 C15 . 1.397(2) ?
C14 C18 . 1.509(2) ?
C15 C16 . 1.384(2) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
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 C11 . . . . 178.17(11) ?
N2 N1 C1 C2 . . . . -175.79(13) ?
N2 N1 C1 C3 . . . . 2.06(19) ?
N1 C1 C2 Cl2 . . . . 1.1(2) ?
C3 C1 C2 Cl2 . . . . -176.74(11) ?
N1 C1 C2 Cl1 . . . . -178.69(10) ?
C3 C1 C2 Cl1 . . . . 3.5(2) ?
C2 C1 C3 C8 . . . . 67.37(19) ?
N1 C1 C3 C8 . . . . -110.35(15) ?
C2 C1 C3 C4 . . . . -113.54(16) ?
N1 C1 C3 C4 . . . . 68.73(18) ?
C8 C3 C4 C5 . . . . -2.2(2) ?
C1 C3 C4 C5 . . . . 178.73(12) ?
C3 C4 C5 C6 . . . . 1.3(2) ?
C4 C5 C6 C7 . . . . 0.5(2) ?
C4 C5 C6 C9 . . . . -179.51(12) ?
C5 C6 C7 C8 . . . . -1.6(2) ?
C9 C6 C7 C8 . . . . 178.48(12) ?
C6 C7 C8 C3 . . . . 0.7(2) ?
C4 C3 C8 C7 . . . . 1.2(2) ?
C1 C3 C8 C7 . . . . -179.74(12) ?
C10 O2 C9 O1 . . . . 1.63(19) ?
C10 O2 C9 C6 . . . . -178.38(11) ?
C7 C6 C9 O1 . . . . 19.0(2) ?
C5 C6 C9 O1 . . . . -161.01(14) ?
C7 C6 C9 O2 . . . . -161.04(12) ?
C5 C6 C9 O2 . . . . 19.00(18) ?
N1 N2 C11 C16 . . . . -11.1(2) ?
N1 N2 C11 C12 . . . . 170.08(13) ?
C16 C11 C12 C13 . . . . 1.5(2) ?
N2 C11 C12 C13 . . . . -179.65(13) ?
C11 C12 C13 C14 . . . . -0.7(2) ?
C11 C12 C13 C17 . . . . 179.96(14) ?
C12 C13 C14 C15 . . . . 0.1(2) ?
C17 C13 C14 C15 . . . . 179.40(14) ?
C12 C13 C14 C18 . . . . -179.55(14) ?
C17 C13 C14 C18 . . . . -0.2(2) ?
C13 C14 C15 C16 . . . . -0.2(2) ?
C18 C14 C15 C16 . . . . 179.48(14) ?
C14 C15 C16 C11 . . . . 0.9(2) ?
C12 C11 C16 C15 . . . . -1.5(2) ?
N2 C11 C16 C15 . . . . 179.72(13) ?
