Crystal structure and Hirshfeld surface analysis of (E)-1-[2,2-di­chloro-1-(4-methyl­phen­yl)ethen­yl]-2-(4-meth­oxy­phen­yl)diazene

Shikhaliyev, N.Q.; Atioğlu, Z.; Akkurt, M.; Qacar, A.M.; Askerov, R.K.; Bhattarai, A.

doi:10.1107/S2056989021008756

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 77| Part 9| September 2021| Pages 965-970

https://doi.org/10.1107/S2056989021008756

Open

access

Crystal structure and Hirshfeld surface analysis of (E)-1-[2,2-dichloro-1-(4-methylphenyl)ethenyl]-2-(4-methoxyphenyl)diazene

Namiq Q. Shikhaliyev,^a Zeliha Atioğlu,^b Mehmet Akkurt,^c Ayten M. Qacar,^a Rizvan K. Askerov ^a and Ajaya Bhattarai ^d ^*

^aOrganic Chemistry Department, Baku State University, Z. Khalilov str. 23, AZ 1148 Baku, Azerbaijan, ^bDepartment of Aircraft Electrics and Electronics, School of Applied Sciences, Cappadocia University, Mustafapaşa, 50420 Ürgüp, Nevşehir, Turkey, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^dDepartment of Chemistry, M.M.A.M.C (Tribhuvan University) Biratnagar, Nepal
^*Correspondence e-mail: bkajaya@yahoo.com

Edited by A. Briceno, Venezuelan Institute of Scientific Research, Venezuela (Received 30 July 2021; accepted 21 August 2021; online 27 August 2021)

The asymmetric unit of the title compound, C₁₆H₁₄Cl₂N₂O, comprises two similar molecules, A and B, in which the dihedral angles between the two aromatic rings are 70.1 (3) and 73.2 (2)°, respectively. The crystal structure features short C—H⋯Cl and C—H⋯O contacts and C—H⋯π and van der Waals interactions. The title compound was refined as a two-component non-merohedral twin, BASF 0.1076 (5). The Hirshfeld surface analysis and two-dimensional fingerprint plots show that H⋯H (38.2% for molecule A; 36.0% for molecule B), Cl⋯H/H⋯Cl (24.6% for molecule A; 26.7% for molecule B) and C⋯H/H⋯C (20.0% for molecule A; 20.2% for molecule B) interactions are the most important contributors to the crystal packing.

Keywords: crystal structure; short C—H⋯Cl contacts; C—H⋯π interactions; van der Waals interactions; Hirshfeld surface analysis.

CCDC reference: 1984582

1. Chemical context

Azo dyes have found a wide range of applications, including as ligands, sensors, optical data storage, liquid crystals, non-linear optical materials, color-changing materials, molecular switches, and dye-sensitized solar cells (Maharramov et al., 2018 ; Mahmudov et al., 2016 ; Viswanathan et al., 2019 ). The functional properties of azo dyes are strongly dependent on the groups attached to the –N=N– synthon. Moreover, non-covalent bond donors or acceptors attached to N-donor azo/hydrazone ligands are of interest because of their high solubility in polar solvents, functional properties, photoactivity in the solid state, coordination ability, and high thermal and oxidative stability (Gurbanov et al., 2020a ,b ; Kopylovich et al., 2011 ; Mac Leod et al., 2012 ; Mahmoudi et al., 2017a ,b , 2018a ,b ). The functionalization of N-donor ligands with –COOH or –SO₃H groups can improve the catalytic activity of the corresponding metal complexes in oxidation and C—C coupling reactions (Gurbanov et al., 2018 ; Ma et al., 2017a ,b , 2020 , 2021 ; Mahmudov et al., 2013 ; Mizar et al., 2012 ; Shixaliyev et al., 2014 ). Thus, in the current work we have synthesized a new azo dye, (E)-1-[2,2-dichloro-1-(4-methylphenyl)ethenyl]-2-(4-methoxyphenyl)diazene, which displays multiple intermolecular non-covalent interactions.

2. Structural commentary

There are two comparable molecules A (with Cl1) and B (with Cl3) in the asymmetric unit of the title compound (Fig. 1). The dihedral angles between the two aromatic rings (C3–C8/C10–C15 and C19–C24/C26–C31) in molecules A and B are 70.1 (3) and 73.2 (2)°, respectively. In molecule A, the N2/N1/C2/C1/Cl1/Cl2 moiety is approximately planar, with a maximum deviation of 0.110 (2) Å, and makes dihedral angles of 1.2 (2) and 71.3 (2)°, respectively, with the C3–C8 and C10–C15 rings. In molecule B, the N4/N3/C18/C17/Cl3/Cl4 moiety is approximately planar with a maximum deviation of 0.046 (6) Å, and makes dihedral angles of 9.57 (18) and 75.94 (19)°, respectively, with the C19–C24 and C26–C31 rings.

Figure 1
Molecules A and B in the asymmetric unit with the atom-labeling scheme and ellipsoids drawn at the 30% probability level.

3. Supramolecular features

In the crystal, no classical hydrogen bonds are observed. The molecules are self-assembled via C—H⋯Cl short contacts, yielding supramolecular chains along the b-axis direction. Adjacent chains are linked by C—H⋯O contacts, generating a two-dimensional array parallel to the bc plane (Table 1, Fig. 2). In addition, molecules are connected by C—H⋯π interactions [Table 2, Fig. 3; C5—H5A⋯Cg2ⁱ, C23—H23A⋯Cg4ⁱⁱ and C25—H25C⋯Cg3ⁱⁱ, where Cg2, Cg3 and Cg4 are the centroids of the benzene rings C10–C15 in molecule A, and C19–C24 and C26–C31 in molecule B, respectively]. The molecular packing is further stabilized by van der Waals interactions.

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg3 and Cg4 are the centroids of the benzene rings C10–C15 (in molecule A) and C19–C24 and C26–C31 (in molecule B), respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯Cg2ⁱ	0.93	2.84	3.645 (8)	146
C23—H23A⋯Cg4ⁱⁱ	0.93	3.00	3.775 (5)	142
C25—H25C⋯Cg3ⁱⁱⁱ	0.96	2.93	3.717 (7)	140
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (iii) .

Table 2
Summary of short interatomic contacts (Å) in the title compound

Contact	Distance	Symmetry operation
Cl1⋯H16C	3.13	−1 − x, $[{1\over 2}]$ + y, 1 − z
Cl1⋯H25B	3.06	−x, − $[{1\over 2}]$ + y, 1 − z
O1⋯H11A	2.88	1 − x, $[{1\over 2}]$ + y, 1 − z
H14A⋯Cl3	3.09	−x, − $[{1\over 2}]$ + y, −z
Cl3⋯H32A	3.03	2 − x, $[{1\over 2}]$ + y, −z
Cl4⋯H27A	2.88	1 + x, y, z

Figure 2
The crystal packing of the title compound viewed along the b axis, showing the C—H⋯Cl and C—H⋯O interactions as dashed lines.

Figure 3
A general view of the C—H⋯π interactions in the title compound. [Symmetry codes: (a) −1 + x, y, z; (b) −x, $[{1\over 2}]$ + y, 1 − z; (c) 1 − x, $[{1\over 2}]$ + y, −z].

4. Hirshfeld surface analysis

To visualize the intermolecular interactions in the title molecule, CrystalExplorer17 (Turner et al., 2017 ) was used to generate Hirshfeld surfaces (McKinnon et al., 2007 ) and their corresponding two-dimensional fingerprint plots (Spackman & McKinnon, 2002 ). In the Hirshfeld surfaces mapped over d_norm for molecules A and B of the title compound (Fig. 4), the bright-red spots near atoms Cl1, Cl3, Cl4 and O1 indicate the short C—H⋯Cl and C—H⋯O contacts (Table 1). Other contacts are equal to or longer than the sum of van der Waals radii. The Hirshfeld surfaces for molecules A and B mapped over electrostatic potential (Spackman et al., 2008 ) are shown in Fig. 5. The positive electrostatic potential (blue regions) over the surface indicates hydrogen-donor potential, whereas the hydrogen-bond acceptors are represented by negative electrostatic potential (red regions).

Figure 4
(a) Front and (b) back views of the Hirshfeld surface of molecule A, and (c) front and (d) back views of the Hirshfeld surface of molecule B plotted over d_norm in the ranges −0.1125 to 1.3054 and −0.1000 to 1.2923 a.u., respectively, for molecules A and B.

Figure 5
Views of the three-dimensional Hirshfeld surfaces of (a) molecule A and (b) molecule B plotted over electrostatic potential energy in the range −0.0500 to 0.0500 a.u. using the STO-3 G basis set at the Hartree–Fock level of theory. The hydrogen-bond donors and acceptors are shown as blue and red regions, respectively, around the atoms corresponding to positive and negative potentials.

The overall two-dimensional fingerprint plot and those delineated into H⋯H, Cl⋯H/H⋯Cl and C⋯H/H⋯C contacts in molecules A and B are illustrated in Fig. 6. The most important interaction is H⋯H, contributing 38.2% for molecule A and 36.0% for molecule B to the overall crystal packing (Fig. 6b). The Cl⋯H/H⋯Cl interactions appear as two symmetrical broad wings with d_e + d_i = 2.70 Å and contribute 24.6% to the Hirshfeld surface for molecule A, and with d_e + d_i = 2.70 Å and contribute 26.7% to the Hirshfeld surface for molecule B (Fig. 6c). The pair of characteristic wings in the fingerprint plot delineated into H⋯C/C⋯H contacts (Fig. 6d; 20.0% contribution for molecule A and 20.2% contribution for molecule B) have the tips at d_e + d_i = 2.80 Å for molecule A and at d_e + d_i = 2.85 Å for molecule B. The remaining contributions for both molecules A and B are from N⋯H/H⋯N, O⋯H/H⋯O, N⋯C/C⋯N, Cl⋯O/O⋯Cl, Cl⋯C/C⋯Cl, C⋯C, Cl⋯N/N⋯Cl, O⋯C/C⋯O and Cl⋯Cl contacts, which are less than 4.6% and have a negligible effect on the packing. The percentage contributions of all interactions are listed in Table 3. The fact that the same interactions make different contributions to the HS for molecules A and B can be attributed to the different molecular environments of the A and B molecules in the crystal structure.

Table 3
Percentage contributions of interatomic contacts to the Hirshfeld surfaces for the molecules A and B of the title compound in the asymmetric unit

Contact	Percentage contribution
	molecule A	molecule B
H⋯H	38.2	36.0
Cl⋯H/H⋯Cl	24.6	26.7
C⋯H/H⋯C	20.0	20.2
N⋯H/H⋯N	4.5	4.6
O⋯H/H⋯O	3.2	3.1
N⋯C/C⋯N	3.1	3.2
Cl⋯O/O⋯Cl	2.0	2.3
Cl⋯C/C⋯Cl	1.8	1.7
C⋯C	1.3	1.2
Cl⋯N/N⋯Cl	1.1	0.9
O⋯C/C⋯O	0.2	0.3
Cl⋯Cl	0.1	0.1

Figure 6
The full two-dimensional fingerprint plots for both molecules A and B showing (a) all interactions, and delineated into (b) H⋯H, (c) Cl⋯H/H⋯Cl and (d) C⋯H/H⋯C interactions. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.

5. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.41, update of November 2019; Groom et al., 2016 ) for the (E)-1-(2,2-dichloro-1-phenylethenyl)-2-phenyldiazene unit resulted in 27 hits. Eight compounds are closely related to the title compound, viz. 4-{2,2-dichloro-1-[(3,5-dimethylphenyl)diazenyl]ethenyl}-N,N-dimethylaniline (GUPHIL; Özkaraca et al., 2020a ), 4-{2,2-dichloro-1-[(4-fluorophenyl)diazenyl]ethenyl}-N,N-dimethylaniline (DULTAI; Özkaraca et al., 2020b ), 1-(4-bromophenyl)-2-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]diazene (HONBOE; Akkurt et al., 2019 ), 1-(4-chlorophenyl)-2-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]diazene (HONBUK; Akkurt et al., 2019), 1-(4-chlorophenyl)-2-[2,2-dichloro-1-(4-fluorophenyl)ethenyl]diazene (HODQAV; Shikhaliyev et al., 2019 ), 1-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]-2-(4-fluorophenyl)diazene (XIZREG; Atioğlu et al., 2019 ), 1,1-[methylenebis(4,1-phenylene)]bis[(2,2-dichloro-1-(4-nitrophenyl)ethenyl]diazene (LEQXIR; Shikhaliyev et al., 2018 ) and 1,1-[methylenebis(4,1-phenylene)]bis{[2,2-dichloro-1-(4-chlorophenyl)ethenyl]diazene} (LEQXOX; Shikhaliyev et al., 2018).

In GUPHIL, the benzene rings subtend a dihedral angle of 77.07 (10)°. In the crystal, molecules are associated into inversion dimers via short Cl⋯Cl contacts [3.3763 (9) Å]. In DULTAI, the dihedral angle between the two aromatic rings is 64.12 (14)°. The crystal structure is stabilized by a short C—H⋯Cl contact, C—Cl⋯π and van der Waals interactions. In HONBOE and HONBUK, the aromatic rings form dihedral angles of 60.9 (2) and 64.1 (2)°, respectively. In the crystals, molecules are linked through weak X⋯Cl contacts (X = Br for HONBOE and Cl for HONBUK), C—H⋯Cl and C—Cl⋯π interactions into sheets parallel to the ab plane. Additional van der Waals interactions consolidate the three-dimensional packing. In HODQAV, the benzene rings make a dihedral angle of 56.13 (13)°. Molecules are stacked in columns along the a-axis direction via weak C—H⋯Cl hydrogen bonds and face-to-face π–π stacking interactions. The crystal packing is further consolidated by short Cl⋯Cl contacts. In XIZREG, the benzene rings form a dihedral angle of 63.29 (8)° and the molecules are linked by C—H⋯O hydrogen bonds into zigzag chains running along the c-axis direction. The crystal packing also features C—Cl⋯π, C—F⋯π and N—O⋯π interactions. In the crystals of LEQXIR and LEQXOX, the dihedral angles between the aromatic rings are 56.18 (12) and 60.31 (14)°, respectively. In LEQXIR, C—H⋯N and C—H⋯O hydrogen bonds and short C—Cl⋯O contacts occur and in LEQXOX, C—H⋯N and short Cl⋯Cl contacts are observed.

6. Synthesis and crystallization

The title compound was synthesized according to a reported method (Mukhtarova et al., 2021 ; Shikhaliyev et al., 2018 , 2019 ). A 20 mL screw-neck vial was charged with DMSO (10 mL), (Z)-1-(4-methoxyphenyl)-2-(4-methylbenzylidene)hydrazine (240 mg, 1 mmol), tetramethylethylenediamine (TMEDA; 295 mg, 2.5 mmol), CuCl (2 mg, 0.02 mmol) and CCl₄ (20 mmol, 10 equiv). After 1–3 h (until TLC analysis showed complete consumption of the corresponding Schiff base), the reaction mixture was poured into a 0.01 M solution of HCl (100 mL, pH = 2–3), and extracted with dichloromethane (3 × 20 mL). The combined organic phase was washed with water (3 × 50 mL) and brine (30 mL), dried over anhydrous Na₂SO₄ and concentrated in vacuo by a rotary evaporator. The residue was purified by column chromatography on silica gel using appropriate mixtures of hexane and dichloromethane (3/1–1/1). Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution. Colorless solid (65%); m.p. 355 K. Analysis calculated for C₁₆H₁₄Cl₂N₂O: C 59.83, H 4.39, N 8.72; found: C 59.78, H 4.32, N 8.69%. ¹H NMR (300 MHz, Chloroform-d) δ 7.79 (d, J = 9.0Hz, 2H, Ar), 7.26 (d, J = 8.0Hz, 2H, Ar), 7.10 (d, J = 8.0Hz, 2H, Ar), 6.95 (d, J = 9.0Hz, 2H, Ar), 3.88 (s, 3H, OCH₃), 2.42 (s, 3H, CH₃). ¹³C NMR (75 MHz, Chloroform-d) δ 162.48, 148.12, 147.82, 138.47, 129.90, 129.76, 129.41, 128.85, 125.23, 114.14, 55.58 and 21.48. ESI–MS: m/z: 322.14 [M + H]⁺.

7. Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 4. All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 or 0.96 Å, and with U_iso(H) = 1.2 or 1.5U_eq(C). Owing to poor agreement between observed and calculated intensities, eight outliers (2 $[\overline{4}]$ 16, 2 $[\overline{10}]$ 15, $[\overline{4}]$ 9 13, $[\overline{5}]$ 5 5, 1 $[\overline{18}]$ 2, $[\overline{4}]$ $[\overline{10}]$ 4, 4 $[\overline{10}]$ 8 and 1 7 11) were omitted in the final cycles of refinement. The title compound was refined as a two-component non-merohedral twin, BASF 0.1076 (5).

Table 4
Experimental details

Crystal data
Chemical formula	C₁₆H₁₄Cl₂N₂O
M_r	321.19
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	5.5366 (3), 17.9208 (8), 16.2085 (8)
β (°)	99.173 (2)
V (Å³)	1587.65 (14)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.41
Crystal size (mm)	0.24 × 0.19 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.675, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	19301, 6444, 3820
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.145, 1.01
No. of reflections	6444
No. of parameters	288
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.32
Absolute structure	Refined as an inversion twin
Absolute structure parameter	0.11 (10)
Computer programs: APEX2 (Bruker, 2007 ), SAINT (Bruker, 2007), SHELXT2016/6 (Sheldrick, 2015a ), SHELXL2016/6 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 1984582

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989021008756/zn2009sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989021008756/zn2009Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989021008756/zn2009Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXT2016/6 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

(E)-1-[2,2-Dichloro-1-(4-methylphenyl)ethenyl]-2-(4-methoxyphenyl)diazene top

Crystal data top

C₁₆H₁₄Cl₂N₂O	F(000) = 664
M_r = 321.19	D_x = 1.344 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 5.5366 (3) Å	Cell parameters from 3046 reflections
b = 17.9208 (8) Å	θ = 2.6–23.3°
c = 16.2085 (8) Å	µ = 0.41 mm⁻¹
β = 99.173 (2)°	T = 296 K
V = 1587.65 (14) Å³	Prism, colourless
Z = 4	0.24 × 0.19 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	3820 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.054
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 26.4°, θ_min = 1.7°
T_min = 0.675, T_max = 0.745	h = −6→6
19301 measured reflections	k = −22→22
6444 independent reflections	l = −20→20

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.059	w = 1/[σ²(F_o²) + (0.0481P)² + 0.5767P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.145	(Δ/σ)_max < 0.001
S = 1.01	Δρ_max = 0.37 e Å⁻³
6444 reflections	Δρ_min = −0.32 e Å⁻³
288 parameters	Absolute structure: Refined as an inversion twin
1 restraint	Absolute structure parameter: 0.11 (10)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	−0.2542 (4)	0.43617 (11)	0.64439 (13)	0.0796 (7)
Cl2	−0.4487 (3)	0.28816 (11)	0.61549 (11)	0.0712 (6)
O1	0.6974 (9)	0.6350 (3)	0.3727 (3)	0.0697 (14)
N1	−0.0135 (10)	0.4111 (3)	0.5003 (4)	0.0535 (14)
N2	0.0904 (10)	0.4034 (3)	0.4371 (3)	0.0489 (13)
C1	−0.2741 (12)	0.3575 (4)	0.5831 (4)	0.0521 (16)
C2	−0.1609 (11)	0.3501 (4)	0.5159 (4)	0.0488 (16)
C3	0.2407 (11)	0.4641 (3)	0.4235 (4)	0.0467 (15)
C4	0.2717 (12)	0.5288 (4)	0.4712 (4)	0.0562 (18)
H4A	0.188500	0.534413	0.516384	0.067*
C5	0.4230 (14)	0.5841 (4)	0.4525 (4)	0.0620 (19)
H5A	0.441835	0.627135	0.484996	0.074*
C6	0.5504 (12)	0.5769 (3)	0.3849 (4)	0.0489 (16)
C7	0.5196 (12)	0.5138 (4)	0.3367 (4)	0.0530 (17)
H7A	0.602750	0.508512	0.291554	0.064*
C8	0.3636 (12)	0.4577 (4)	0.3556 (4)	0.0527 (17)
H8A	0.341397	0.415233	0.322199	0.063*
C9	0.8362 (14)	0.6303 (4)	0.3075 (5)	0.075 (2)
H9A	0.958880	0.668681	0.314241	0.113*
H9B	0.730904	0.636837	0.254871	0.113*
H9C	0.913688	0.582341	0.308698	0.113*
C10	−0.1948 (11)	0.2833 (3)	0.4611 (4)	0.0434 (14)
C11	−0.0071 (12)	0.2325 (4)	0.4599 (5)	0.064 (2)
H11A	0.141146	0.239262	0.495082	0.076*
C12	−0.0390 (14)	0.1719 (4)	0.4065 (5)	0.067 (2)
H12A	0.087072	0.137412	0.407601	0.080*
C13	−0.2533 (14)	0.1614 (4)	0.3519 (4)	0.0596 (19)
C14	−0.4408 (13)	0.2110 (4)	0.3547 (4)	0.0577 (18)
H14A	−0.589706	0.203698	0.320052	0.069*
C15	−0.4119 (11)	0.2715 (3)	0.4082 (4)	0.0464 (15)
H15A	−0.540900	0.304650	0.408564	0.056*
C16	−0.2854 (17)	0.0945 (5)	0.2927 (5)	0.091 (3)
H16A	−0.140574	0.064261	0.302099	0.136*
H16B	−0.312419	0.111859	0.235935	0.136*
H16C	−0.423307	0.065509	0.302905	0.136*
Cl3	0.7604 (5)	0.70082 (12)	−0.12906 (13)	0.0884 (8)
Cl4	0.9416 (4)	0.55116 (12)	−0.10328 (12)	0.0782 (7)
O2	−0.2060 (9)	0.9018 (3)	0.1289 (3)	0.0741 (15)
N3	0.5200 (11)	0.6762 (3)	0.0147 (3)	0.0547 (14)
N4	0.4238 (10)	0.6706 (3)	0.0789 (3)	0.0548 (14)
C17	0.7780 (13)	0.6217 (4)	−0.0682 (4)	0.0569 (18)
C18	0.6653 (12)	0.6147 (4)	−0.0012 (4)	0.0514 (17)
C19	0.2694 (8)	0.7321 (2)	0.0907 (3)	0.0629 (6)
C20	0.1554 (8)	0.7291 (2)	0.1610 (3)	0.0629 (6)
H20A	0.186090	0.689285	0.198089	0.076*
C21	−0.0044 (8)	0.7855 (3)	0.1760 (2)	0.0629 (6)
H21A	−0.080656	0.783412	0.223126	0.076*
C22	−0.0502 (8)	0.8449 (2)	0.1207 (3)	0.0629 (6)
C23	0.0638 (9)	0.8479 (2)	0.0503 (3)	0.0629 (6)
H23A	0.033133	0.887707	0.013237	0.076*
C24	0.2236 (8)	0.7915 (2)	0.0353 (2)	0.0629 (6)
H24A	0.299880	0.793580	−0.011802	0.076*
C25	−0.3465 (13)	0.9007 (4)	0.1949 (4)	0.0629 (6)
H25A	−0.457475	0.942189	0.189000	0.094*
H25B	−0.239456	0.904082	0.247500	0.094*
H25C	−0.437714	0.854952	0.192725	0.094*
C26	0.6954 (9)	0.5466 (2)	0.0525 (3)	0.0629 (6)
C27	0.5076 (7)	0.4946 (2)	0.0485 (3)	0.0629 (6)
H27A	0.361256	0.502241	0.012536	0.076*
C28	0.5386 (7)	0.4311 (2)	0.0983 (3)	0.0629 (6)
H28A	0.412980	0.396257	0.095678	0.076*
C29	0.7573 (8)	0.4196 (2)	0.1521 (3)	0.0629 (6)
C30	0.9451 (7)	0.4716 (3)	0.1560 (3)	0.0629 (6)
H30A	1.091434	0.463884	0.192023	0.076*
C31	0.9141 (7)	0.5351 (2)	0.1062 (3)	0.0629 (6)
H31A	1.039714	0.569868	0.108882	0.076*
C32	0.7922 (16)	0.3491 (4)	0.2055 (5)	0.086 (3)
H32A	0.926377	0.320655	0.190966	0.129*
H32B	0.645678	0.319578	0.195512	0.129*
H32C	0.826528	0.362584	0.263450	0.129*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0944 (16)	0.0730 (15)	0.0764 (13)	−0.0152 (12)	0.0289 (12)	−0.0239 (11)
Cl2	0.0750 (13)	0.0808 (15)	0.0611 (11)	−0.0262 (11)	0.0212 (10)	−0.0003 (10)
O1	0.080 (4)	0.051 (3)	0.088 (4)	−0.016 (3)	0.042 (3)	−0.005 (3)
N1	0.056 (4)	0.044 (3)	0.062 (3)	−0.005 (3)	0.013 (3)	0.000 (3)
N2	0.056 (3)	0.040 (3)	0.051 (3)	0.002 (3)	0.009 (3)	0.001 (2)
C1	0.051 (4)	0.053 (4)	0.052 (4)	−0.007 (3)	0.008 (3)	−0.003 (3)
C2	0.049 (4)	0.046 (4)	0.053 (4)	−0.003 (3)	0.011 (3)	0.003 (3)
C3	0.058 (4)	0.034 (3)	0.050 (4)	−0.008 (3)	0.016 (3)	−0.001 (3)
C4	0.069 (5)	0.050 (4)	0.057 (4)	−0.015 (4)	0.031 (4)	−0.012 (3)
C5	0.084 (5)	0.048 (4)	0.060 (4)	−0.014 (4)	0.031 (4)	−0.018 (3)
C6	0.053 (4)	0.042 (4)	0.054 (4)	0.004 (3)	0.016 (3)	0.002 (3)
C7	0.060 (4)	0.051 (4)	0.053 (4)	0.001 (3)	0.024 (3)	−0.005 (3)
C8	0.069 (4)	0.039 (4)	0.053 (4)	−0.005 (3)	0.018 (3)	−0.004 (3)
C9	0.083 (6)	0.072 (5)	0.080 (5)	−0.010 (4)	0.041 (5)	0.015 (4)
C10	0.045 (3)	0.036 (3)	0.051 (3)	−0.004 (3)	0.013 (3)	0.001 (3)
C11	0.042 (4)	0.054 (5)	0.094 (6)	0.003 (3)	0.007 (4)	−0.002 (4)
C12	0.061 (5)	0.045 (4)	0.098 (6)	0.009 (4)	0.021 (4)	−0.001 (4)
C13	0.073 (5)	0.049 (4)	0.062 (4)	0.002 (4)	0.027 (4)	−0.002 (3)
C14	0.062 (5)	0.065 (5)	0.046 (4)	−0.004 (4)	0.008 (3)	−0.001 (3)
C15	0.043 (4)	0.047 (4)	0.049 (3)	0.008 (3)	0.007 (3)	0.005 (3)
C16	0.123 (8)	0.062 (5)	0.091 (6)	−0.001 (5)	0.027 (6)	−0.021 (5)
Cl3	0.125 (2)	0.0759 (16)	0.0683 (13)	0.0050 (13)	0.0272 (13)	0.0208 (11)
Cl4	0.0905 (17)	0.0858 (16)	0.0647 (12)	0.0200 (12)	0.0323 (11)	0.0026 (11)
O2	0.080 (4)	0.061 (3)	0.087 (4)	0.017 (3)	0.032 (3)	0.010 (3)
N3	0.065 (4)	0.048 (4)	0.054 (3)	0.004 (3)	0.019 (3)	0.005 (3)
N4	0.066 (4)	0.048 (3)	0.052 (3)	0.000 (3)	0.013 (3)	−0.001 (3)
C17	0.063 (5)	0.057 (4)	0.052 (4)	0.005 (4)	0.011 (4)	0.001 (3)
C18	0.057 (4)	0.047 (4)	0.049 (4)	0.003 (3)	0.005 (3)	−0.008 (3)
C19	0.0714 (16)	0.0556 (14)	0.0645 (13)	0.0030 (11)	0.0190 (11)	0.0027 (10)
C20	0.0714 (16)	0.0556 (14)	0.0645 (13)	0.0030 (11)	0.0190 (11)	0.0027 (10)
C21	0.0714 (16)	0.0556 (14)	0.0645 (13)	0.0030 (11)	0.0190 (11)	0.0027 (10)
C22	0.0714 (16)	0.0556 (14)	0.0645 (13)	0.0030 (11)	0.0190 (11)	0.0027 (10)
C23	0.0714 (16)	0.0556 (14)	0.0645 (13)	0.0030 (11)	0.0190 (11)	0.0027 (10)
C24	0.0714 (16)	0.0556 (14)	0.0645 (13)	0.0030 (11)	0.0190 (11)	0.0027 (10)
C25	0.0714 (16)	0.0556 (14)	0.0645 (13)	0.0030 (11)	0.0190 (11)	0.0027 (10)
C26	0.0714 (16)	0.0556 (14)	0.0645 (13)	0.0030 (11)	0.0190 (11)	0.0027 (10)
C27	0.0714 (16)	0.0556 (14)	0.0645 (13)	0.0030 (11)	0.0190 (11)	0.0027 (10)
C28	0.0714 (16)	0.0556 (14)	0.0645 (13)	0.0030 (11)	0.0190 (11)	0.0027 (10)
C29	0.0714 (16)	0.0556 (14)	0.0645 (13)	0.0030 (11)	0.0190 (11)	0.0027 (10)
C30	0.0714 (16)	0.0556 (14)	0.0645 (13)	0.0030 (11)	0.0190 (11)	0.0027 (10)
C31	0.0714 (16)	0.0556 (14)	0.0645 (13)	0.0030 (11)	0.0190 (11)	0.0027 (10)
C32	0.120 (8)	0.064 (6)	0.079 (6)	0.005 (5)	0.030 (5)	0.004 (4)

Geometric parameters (Å, º) top

Cl1—C1	1.717 (7)	Cl3—C17	1.721 (7)
Cl2—C1	1.708 (7)	Cl4—C17	1.704 (7)
O1—C6	1.355 (7)	O2—C22	1.356 (5)
O1—C9	1.406 (8)	O2—C25	1.419 (8)
N1—N2	1.260 (7)	N3—N4	1.247 (7)
N1—C2	1.411 (8)	N3—C18	1.413 (8)
N2—C3	1.408 (7)	N4—C19	1.426 (6)
C1—C2	1.347 (9)	C17—C18	1.342 (9)
C2—C10	1.486 (8)	C18—C26	1.493 (7)
C3—C8	1.388 (8)	C19—C20	1.3900
C3—C4	1.390 (8)	C19—C24	1.3900
C4—C5	1.363 (9)	C20—C21	1.3900
C4—H4A	0.9300	C20—H20A	0.9300
C5—C6	1.401 (9)	C21—C22	1.3900
C5—H5A	0.9300	C21—H21A	0.9300
C6—C7	1.369 (8)	C22—C23	1.3900
C7—C8	1.391 (8)	C23—C24	1.3900
C7—H7A	0.9300	C23—H23A	0.9300
C8—H8A	0.9300	C24—H24A	0.9300
C9—H9A	0.9600	C25—H25A	0.9600
C9—H9B	0.9600	C25—H25B	0.9600
C9—H9C	0.9600	C25—H25C	0.9600
C10—C15	1.376 (8)	C26—C27	1.3900
C10—C11	1.384 (8)	C26—C31	1.3900
C11—C12	1.383 (9)	C27—C28	1.3900
C11—H11A	0.9300	C27—H27A	0.9300
C12—C13	1.375 (10)	C28—C29	1.3900
C12—H12A	0.9300	C28—H28A	0.9300
C13—C14	1.373 (9)	C29—C30	1.3900
C13—C16	1.527 (10)	C29—C32	1.526 (8)
C14—C15	1.382 (8)	C30—C31	1.3900
C14—H14A	0.9300	C30—H30A	0.9300
C15—H15A	0.9300	C31—H31A	0.9300
C16—H16A	0.9600	C32—H32A	0.9600
C16—H16B	0.9600	C32—H32B	0.9600
C16—H16C	0.9600	C32—H32C	0.9600

C6—O1—C9	118.5 (6)	C22—O2—C25	119.8 (5)
N2—N1—C2	114.4 (5)	N4—N3—C18	114.9 (5)
N1—N2—C3	113.6 (5)	N3—N4—C19	113.2 (5)
C2—C1—Cl2	122.4 (5)	C18—C17—Cl4	122.7 (6)
C2—C1—Cl1	123.6 (5)	C18—C17—Cl3	123.4 (6)
Cl2—C1—Cl1	114.0 (4)	Cl4—C17—Cl3	113.9 (4)
C1—C2—N1	115.2 (6)	C17—C18—N3	115.2 (6)
C1—C2—C10	122.2 (6)	C17—C18—C26	121.7 (6)
N1—C2—C10	122.6 (5)	N3—C18—C26	123.1 (5)
C8—C3—C4	118.6 (6)	C20—C19—C24	120.0
C8—C3—N2	115.9 (6)	C20—C19—N4	116.1 (4)
C4—C3—N2	125.5 (5)	C24—C19—N4	123.9 (4)
C5—C4—C3	120.5 (6)	C19—C20—C21	120.0
C5—C4—H4A	119.7	C19—C20—H20A	120.0
C3—C4—H4A	119.7	C21—C20—H20A	120.0
C4—C5—C6	120.8 (6)	C22—C21—C20	120.0
C4—C5—H5A	119.6	C22—C21—H21A	120.0
C6—C5—H5A	119.6	C20—C21—H21A	120.0
O1—C6—C7	125.1 (6)	O2—C22—C21	124.5 (4)
O1—C6—C5	115.6 (6)	O2—C22—C23	115.5 (4)
C7—C6—C5	119.3 (6)	C21—C22—C23	120.0
C6—C7—C8	119.8 (6)	C24—C23—C22	120.0
C6—C7—H7A	120.1	C24—C23—H23A	120.0
C8—C7—H7A	120.1	C22—C23—H23A	120.0
C3—C8—C7	120.9 (6)	C23—C24—C19	120.0
C3—C8—H8A	119.5	C23—C24—H24A	120.0
C7—C8—H8A	119.5	C19—C24—H24A	120.0
O1—C9—H9A	109.5	O2—C25—H25A	109.5
O1—C9—H9B	109.5	O2—C25—H25B	109.5
H9A—C9—H9B	109.5	H25A—C25—H25B	109.5
O1—C9—H9C	109.5	O2—C25—H25C	109.5
H9A—C9—H9C	109.5	H25A—C25—H25C	109.5
H9B—C9—H9C	109.5	H25B—C25—H25C	109.5
C15—C10—C11	118.2 (6)	C27—C26—C31	120.0
C15—C10—C2	120.7 (6)	C27—C26—C18	120.5 (4)
C11—C10—C2	121.0 (6)	C31—C26—C18	119.5 (4)
C12—C11—C10	120.3 (7)	C28—C27—C26	120.0
C12—C11—H11A	119.9	C28—C27—H27A	120.0
C10—C11—H11A	119.9	C26—C27—H27A	120.0
C13—C12—C11	121.4 (7)	C27—C28—C29	120.0
C13—C12—H12A	119.3	C27—C28—H28A	120.0
C11—C12—H12A	119.3	C29—C28—H28A	120.0
C14—C13—C12	118.0 (7)	C30—C29—C28	120.0
C14—C13—C16	121.0 (7)	C30—C29—C32	120.2 (5)
C12—C13—C16	120.9 (7)	C28—C29—C32	119.8 (5)
C13—C14—C15	121.1 (7)	C29—C30—C31	120.0
C13—C14—H14A	119.5	C29—C30—H30A	120.0
C15—C14—H14A	119.5	C31—C30—H30A	120.0
C10—C15—C14	120.9 (6)	C30—C31—C26	120.0
C10—C15—H15A	119.6	C30—C31—H31A	120.0
C14—C15—H15A	119.6	C26—C31—H31A	120.0
C13—C16—H16A	109.5	C29—C32—H32A	109.5
C13—C16—H16B	109.5	C29—C32—H32B	109.5
H16A—C16—H16B	109.5	H32A—C32—H32B	109.5
C13—C16—H16C	109.5	C29—C32—H32C	109.5
H16A—C16—H16C	109.5	H32A—C32—H32C	109.5
H16B—C16—H16C	109.5	H32B—C32—H32C	109.5

C2—N1—N2—C3	−178.8 (5)	C18—N3—N4—C19	−177.2 (5)
Cl2—C1—C2—N1	−176.8 (5)	Cl4—C17—C18—N3	−174.6 (5)
Cl1—C1—C2—N1	2.5 (9)	Cl3—C17—C18—N3	2.6 (9)
Cl2—C1—C2—C10	4.8 (9)	Cl4—C17—C18—C26	6.0 (10)
Cl1—C1—C2—C10	−175.9 (5)	Cl3—C17—C18—C26	−176.8 (5)
N2—N1—C2—C1	−179.8 (6)	N4—N3—C18—C17	−177.2 (6)
N2—N1—C2—C10	−1.4 (9)	N4—N3—C18—C26	2.2 (9)
N1—N2—C3—C8	178.7 (6)	N3—N4—C19—C20	179.7 (4)
N1—N2—C3—C4	−2.2 (9)	N3—N4—C19—C24	1.8 (7)
C8—C3—C4—C5	−1.1 (11)	C24—C19—C20—C21	0.0
N2—C3—C4—C5	179.7 (7)	N4—C19—C20—C21	−178.0 (5)
C3—C4—C5—C6	−0.1 (11)	C19—C20—C21—C22	0.0
C9—O1—C6—C7	−2.0 (10)	C25—O2—C22—C21	−4.0 (8)
C9—O1—C6—C5	178.1 (6)	C25—O2—C22—C23	174.8 (5)
C4—C5—C6—O1	−179.3 (7)	C20—C21—C22—O2	178.8 (5)
C4—C5—C6—C7	0.8 (11)	C20—C21—C22—C23	0.0
O1—C6—C7—C8	179.9 (6)	O2—C22—C23—C24	−178.9 (5)
C5—C6—C7—C8	−0.3 (10)	C21—C22—C23—C24	0.0
C4—C3—C8—C7	1.6 (10)	C22—C23—C24—C19	0.0
N2—C3—C8—C7	−179.2 (6)	C20—C19—C24—C23	0.0
C6—C7—C8—C3	−0.9 (10)	N4—C19—C24—C23	177.8 (5)
C1—C2—C10—C15	71.9 (8)	C17—C18—C26—C27	−105.8 (6)
N1—C2—C10—C15	−106.4 (7)	N3—C18—C26—C27	74.8 (7)
C1—C2—C10—C11	−110.1 (7)	C17—C18—C26—C31	73.7 (7)
N1—C2—C10—C11	71.6 (8)	N3—C18—C26—C31	−105.7 (6)
C15—C10—C11—C12	0.2 (10)	C31—C26—C27—C28	0.0
C2—C10—C11—C12	−177.9 (6)	C18—C26—C27—C28	179.5 (5)
C10—C11—C12—C13	1.9 (11)	C26—C27—C28—C29	0.0
C11—C12—C13—C14	−3.4 (11)	C27—C28—C29—C30	0.0
C11—C12—C13—C16	179.4 (7)	C27—C28—C29—C32	−178.9 (5)
C12—C13—C14—C15	2.8 (10)	C28—C29—C30—C31	0.0
C16—C13—C14—C15	180.0 (6)	C32—C29—C30—C31	178.9 (5)
C11—C10—C15—C14	−0.7 (9)	C29—C30—C31—C26	0.0
C2—C10—C15—C14	177.4 (5)	C27—C26—C31—C30	0.0
C13—C14—C15—C10	−0.8 (10)	C18—C26—C31—C30	−179.5 (5)

Hydrogen-bond geometry (Å, º) top

Cg2, Cg3 and Cg4 are the centroids of the benzene rings C10–C15 (in molecule A) and C19–C24 and C26–C31 (in molecule B), respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···Cg2ⁱ	0.93	2.84	3.645 (8)	146
C23—H23A···Cg4ⁱⁱ	0.93	3.00	3.775 (5)	142
C25—H25C···Cg3ⁱⁱⁱ	0.96	2.93	3.717 (7)	140

Symmetry codes: (i) −x, y+1/2, −z+1; (ii) −x+1, y+1/2, −z; (iii) x−1, y, z.

Summary of short interatomic contacts (Å) in the title compound top

Contact	Distance	Symmetry operation
Cl1···H16C	3.13	-1 - x, 1/2 + y, 1 - z
Cl1···H25B	3.06	-x, -1/2 + y, 1 - z
O1···H11A	2.88	1 - x, 1/2 + y, 1 - z
H14A···Cl3	3.09	-x, -1/2 + y, -z
Cl3···H32A	3.03	2 - x, 1/2 + y, -z
Cl4···H27A	2.88	1 + x, y, z

Percentage contributions of interatomic contacts to the Hirshfeld surfaces for the molecules A and B of the title compound in the asymmetric unit top

Contact	Percentage contribution	Percentage contribution
	molecule A	molecule B
H···H	38.2	36.0
Cl···H/H···Cl	24.6	26.7
C···H/H···C	20.0	20.2
N···H/H···N	4.5	4.6
O···H/H···O	3.2	3.1
N···C/C···N	3.1	3.2
Cl···O/O···Cl	2.0	2.3
Cl···C/C···Cl	1.8	1.7
C···C	1.3	1.2
Cl···N/N···Cl	1.1	0.9
O···C/C···O	0.2	0.3
Cl···Cl	0.1	0.1

Acknowledgements

The authors' contributions are as follows. Conceptualization, NQS, MA and AB; synthesis, AMQ; X-ray analysis, RKA, ZA and MA; writing (review and editing of the manuscript), NQS, AMQ and RKA; funding acquisition, NQS, AMQ and RKA; supervision, NQS, MA and AB.

Funding information

This work was performed under the support of the Science Development Foundation under the President of the Republic of Azerbaijan (grant No. EIF-BGM-4-RFTF-1/2017–21/13/4).

References

Akkurt, M., Shikhaliyev, N. Q., Suleymanova, G. T., Babayeva, G. V., Mammadova, G. Z., Niyazova, A. A., Shikhaliyeva, I. M. & Toze, F. A. A. (2019). Acta Cryst. E75, 1199–1204. Web of Science CSD CrossRef IUCr Journals Google Scholar
Atioğlu, Z., Akkurt, M., Shikhaliyev, N. Q., Suleymanova, G. T., Bagirova, K. N. & Toze, F. A. A. (2019). Acta Cryst. E75, 237–241. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Gurbanov, A. V., Kuznetsov, M. L., Demukhamedova, S. D., Alieva, I. N., Godjaev, N. M., Zubkov, F. I., Mahmudov, K. T. & Pombeiro, A. J. L. (2020a). CrystEngComm, 22, 628–633. Web of Science CSD CrossRef CAS Google Scholar
Gurbanov, A. V., Kuznetsov, M. L., Mahmudov, K. T., Pombeiro, A. J. L. & Resnati, G. (2020b). Chem. Eur. J. 26, 14833–14837. Web of Science CSD CrossRef CAS PubMed Google Scholar
Gurbanov, A. V., Mahmoudi, G., Guedes da Silva, M. F. C., Zubkov, F. I., Mahmudov, K. T. & Pombeiro, A. J. L. (2018). Inorg. Chim. Acta, 471, 130–136. Web of Science CSD CrossRef CAS Google Scholar
Kopylovich, M. N., Mahmudov, K. T., Mizar, A. & Pombeiro, A. J. L. (2011). Chem. Commun. 47, 7248–7250. Web of Science CrossRef CAS Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CSD CrossRef ICSD CAS IUCr Journals Google Scholar
Ma, Z., Gurbanov, A. V., Maharramov, A. M., Guseinov, F. I., Kopylovich, M. N., Zubkov, F. I., Mahmudov, K. T. & Pombeiro, A. J. L. (2017a). J. Mol. Catal. A Chem. 426, 526–533. Web of Science CSD CrossRef CAS Google Scholar
Ma, Z., Gurbanov, A. V., Sutradhar, M., Kopylovich, M. N., Mahmudov, K. T., Maharramov, A. M., Guseinov, F. I., Zubkov, F. I. & Pombeiro, A. J. L. (2017b). Mol. Catal. 428, 17–23. Web of Science CSD CrossRef CAS Google Scholar
Ma, Z., Mahmudov, K. T., Aliyeva, V. A., Gurbanov, A. V., Guedes da Silva, M. F. C. & Pombeiro, A. J. L. (2021). Coord. Chem. Rev. 437, 213859. Web of Science CrossRef Google Scholar
Ma, Z., Mahmudov, K. T., Aliyeva, V. A., Gurbanov, A. V. & Pombeiro, A. J. L. (2020). Coord. Chem. Rev. 423, 213482. Web of Science CrossRef Google Scholar
Mac Leod, T. C., Kopylovich, M. N., Guedes da Silva, M. F. C., Mahmudov, K. T. & Pombeiro, A. J. L. (2012). Appl. Catal. Gen. 439–440, 15–23. Web of Science CrossRef CAS Google Scholar
Maharramov, A. M., Shikhaliyev, N. Q., Suleymanova, G. T., Gurbanov, A. V., Babayeva, G. V., Mammadova, G. Z., Zubkov, F. I., Nenajdenko, V. G., Mahmudov, K. T. & Pombeiro, A. J. L. (2018). Dyes Pigments, 159, 135–141. Web of Science CrossRef CAS Google Scholar
Mahmoudi, G., Afkhami, F. A., Castiñeiras, A., García-Santos, I., Gurbanov, A., Zubkov, F. I., Mitoraj, M. P., Kukułka, M., Sagan, F., Szczepanik, D. W., Konyaeva, I. A. & Safin, D. A. (2018a). Inorg. Chem. 57, 4395–4408. Web of Science CSD CrossRef CAS PubMed Google Scholar
Mahmoudi, G., Gurbanov, A. V., Rodríguez-Hermida, S., Carballo, R., Amini, M., Bacchi, A., Mitoraj, M. P., Sagan, F., Kukułka, M. & Safin, D. A. (2017b). Inorg. Chem. 56, 9698–9709. Web of Science CSD CrossRef CAS PubMed Google Scholar
Mahmoudi, G., Zangrando, E., Mitoraj, M. P., Gurbanov, A. V., Zubkov, F. I., Moosavifar, M., Konyaeva, I. A., Kirillov, A. M. & Safin, D. A. (2018b). New J. Chem. 42, 4959–4971. Web of Science CSD CrossRef CAS Google Scholar
Mahmoudi, G., Zaręba, J. K., Gurbanov, A. V., Bauzá, A., Zubkov, F. I., Kubicki, M., Stilinović, V., Kinzhybalo, V. & Frontera, A. (2017a). Eur. J. Inorg. Chem. pp. 4763–4772. Web of Science CSD CrossRef Google Scholar
Mahmudov, K. T., Kopylovich, M. N., Haukka, M., Mahmudova, G. S., Esmaeila, E. F., Chyragov, F. M. & Pombeiro, A. J. L. (2013). J. Mol. Struct. 1048, 108–112. Web of Science CSD CrossRef CAS Google Scholar
Mahmudov, K. T. & Pombeiro, A. J. L. (2016). Chem. Eur. J. 22, 16356–16398. Web of Science CrossRef CAS PubMed Google Scholar
McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814–3816. Web of Science CrossRef Google Scholar
Mizar, A., Guedes da Silva, M. F. C., Kopylovich, M. N., Mukherjee, S., Mahmudov, K. T. & Pombeiro, A. J. L. (2012). Eur. J. Inorg. Chem. pp. 2305–2313. Web of Science CSD CrossRef Google Scholar
Mukhtarova, S. H. (2021). New Materials, Compounds and Applications, 5, 45–51. Google Scholar
Özkaraca, K., Akkurt, M., Shikhaliyev, N. Q., Askerova, U. F., Suleymanova, G. T., Mammadova, G. Z. & Shadrack, D. M. (2020a). Acta Cryst. E76, 1251–1254. CrossRef IUCr Journals Google Scholar
Özkaraca, K., Akkurt, M., Shikhaliyev, N. Q., Askerova, U. F., Suleymanova, G. T., Shikhaliyeva, I. M. & Bhattarai, A. (2020b). Acta Cryst. E76, 811–815. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Shikhaliyev, N. Q., Ahmadova, N. E., Gurbanov, A. V., Maharramov, A. M., Mammadova, G. Z., Nenajdenko, V. G., Zubkov, F. I., Mahmudov, K. T. & Pombeiro, A. J. L. (2018). Dyes Pigments, 150, 377–381. Web of Science CSD CrossRef CAS Google Scholar
Shikhaliyev, N. Q., Ahmadova, N. E., Gurbanov, A. V., Maharramov, A. M., Mammadova, G. Z., Nenajdenko, V. G., Zubkov, F. I., Mahmudov, K. T. & Pombeiro, A. J. L. (2018). Dyes Pigments, 150, 377–381. Web of Science CSD CrossRef CAS Google Scholar
Shikhaliyev, N. Q., Çelikesir, S. T., Akkurt, M., Bagirova, K. N., Suleymanova, G. T. & Toze, F. A. A. (2019). Acta Cryst. E75, 465–469. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shikhaliyev, N. Q., Kuznetsov, M. L., Maharramov, A. M., Gurbanov, A. V., Ahmadova, N. E., Nenajdenko, V. G., Mahmudov, K. T. & Pombeiro, A. J. L. (2019). CrystEngComm, 21, 5032–5038. Web of Science CSD CrossRef CAS Google Scholar
Shixaliyev, N. Q., Gurbanov, A. V., Maharramov, A. M., Mahmudov, K. T., Kopylovich, M. N., Martins, L. M. D. R. S., Muzalevskiy, V. M., Nenajdenko, V. G. & Pombeiro, A. J. L. (2014). New J. Chem. 38, 4807–4815. Web of Science CSD CrossRef CAS Google Scholar
Spackman, M. A. & McKinnon, J. J. (2002). CrystEngComm, 4, 378–392. Web of Science CrossRef CAS Google Scholar
Spackman, M. A., McKinnon, J. J. & Jayatilaka, D. (2008). CrystEngComm, 10, 377–388. CAS Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). CrystalExplorer17. The University of Western Australia. Google Scholar
Viswanathan, A., Kute, D., Musa, A., Konda Mani, S., Sipilä, V., Emmert-Streib, F., Zubkov, F. I., Gurbanov, A. V., Yli-Harja, O. & Kandhavelu, M. (2019). Eur. J. Med. Chem. 166, 291–303. CrossRef CAS PubMed Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.