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

Namiq Q Shikhaliyev; Zeliha Atioğlu; Mehmet Akkurt; Ayten M Qacar; Rizvan K Askerov; Ajaya Bhattarai

doi:10.1107/S2056989021008756

. 2021 Aug 27;77(Pt 9):965–970. doi: 10.1107/S2056989021008756

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, Ajaya Bhattarai ^d,^*

PMCID: PMC8423004 PMID: 34584771

Two similar molecules make up the asymmetric unit of the title compound. The crystal structure features short C—H⋯Cl and C—H⋯O contacts and C—H⋯π and van der Waals interactions.

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

Abstract

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.

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.

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.

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

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

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Symmetry codes: (i) -x, y+{\script{1\over 2}}, -z+1; (ii) -x+1, y+{\script{1\over 2}}, -z; (iii) x-1, y, z.

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.

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

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

Inline graphic — A general view of the C—H⋯π interactions in the title compound. [Symmetry codes: (a) −1 + x, y, z; (b) −x, + y, 1 − z; (c) 1 − x, + y, −z].

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).

(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.

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. 6 ▸ b). 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. 6 ▸ c). The pair of characteristic wings in the fingerprint plot delineated into H⋯C/C⋯H contacts (Fig. 6 ▸ d; 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.

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.

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

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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.

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]⁺.

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 Inline graphic 16, 2 15, 9 13, 5 5, 1 2, 4, 4 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(F ²)], wR(F ²), 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)

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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 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989021008756/zn2009sup1.cif

e-77-00965-sup1.cif^{(582.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989021008756/zn2009Isup2.hkl

e-77-00965-Isup2.hkl^{(512.1KB, hkl)}

Click here for additional data file.^{(5.7KB, cml)}

Supporting information file. DOI: 10.1107/S2056989021008756/zn2009Isup3.cml

CCDC reference: 1984582

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Crystal data

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

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Data collection

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

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Refinement

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)

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Special details

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.

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

	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*

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Atomic displacement parameters (Å²)

	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)

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Geometric parameters (Å, º)

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)

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Hydrogen-bond geometry (Å, º)

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

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

Funding Statement

This work was funded by Science Development Foundation under the President of the Republic of Azerbaijan grant EIF-BGM-4- RFTF-1/2017–21/13/4).

References

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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. [DOI] [PubMed]
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. [DOI] [PubMed]
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.
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.
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.
Mahmudov, K. T. & Pombeiro, A. J. L. (2016). Chem. Eur. J. 22, 16356–16398. [DOI] [PubMed]
McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814–3816. [DOI] [PubMed]
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.
Mukhtarova, S. H. (2021). New Materials, Compounds and Applications, 5, 45–51.
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. [DOI] [PMC free article] [PubMed]
Özkaraca, K., Akkurt, M., Shikhaliyev, N. Q., Askerova, U. F., Suleymanova, G. T., Shikhaliyeva, I. M. & Bhattarai, A. (2020b). Acta Cryst. E76, 811–815. [DOI] [PMC free article] [PubMed]
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.
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.
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.
Shikhaliyev, N. Q., Çelikesir, S. T., Akkurt, M., Bagirova, K. N., Suleymanova, G. T. & Toze, F. A. A. (2019). Acta Cryst. E75, 465–469. [DOI] [PMC free article] [PubMed]
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.
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.
Spackman, M. A. & McKinnon, J. J. (2002). CrystEngComm, 4, 378–392.
Spackman, M. A., McKinnon, J. J. & Jayatilaka, D. (2008). CrystEngComm, 10, 377–388.
Spek, A. L. (2020). Acta Cryst. E76, 1–11. [DOI] [PMC free article] [PubMed]
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.
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. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989021008756/zn2009sup1.cif

e-77-00965-sup1.cif^{(582.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989021008756/zn2009Isup2.hkl

e-77-00965-Isup2.hkl^{(512.1KB, hkl)}

Click here for additional data file.^{(5.7KB, cml)}

Supporting information file. DOI: 10.1107/S2056989021008756/zn2009Isup3.cml

CCDC reference: 1984582

Additional supporting information: crystallographic information; 3D view; checkCIF report

[bb1] 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. [DOI] [PMC free article] [PubMed]

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[bb7] Gurbanov, A. V., Kuznetsov, M. L., Mahmudov, K. T., Pombeiro, A. J. L. & Resnati, G. (2020b). Chem. Eur. J. 26, 14833–14837. [DOI] [PubMed]

[bb8] 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.

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[bb11] 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.

[bb12] 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.

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[bb14] Ma, Z., Mahmudov, K. T., Aliyeva, V. A., Gurbanov, A. V. & Pombeiro, A. J. L. (2020). Coord. Chem. Rev. 423, 213482.

[bb15] 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.

[bb16] 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.

[bb17] 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. [DOI] [PubMed]

[bb18] 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. [DOI] [PubMed]

[bb19] 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.

[bb20] 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.

[bb21] 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.

[bb22] Mahmudov, K. T. & Pombeiro, A. J. L. (2016). Chem. Eur. J. 22, 16356–16398. [DOI] [PubMed]

[bb23] McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814–3816. [DOI] [PubMed]

[bb24] 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.

[bb25] Mukhtarova, S. H. (2021). New Materials, Compounds and Applications, 5, 45–51.

[bb26] 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. [DOI] [PMC free article] [PubMed]

[bb27] Özkaraca, K., Akkurt, M., Shikhaliyev, N. Q., Askerova, U. F., Suleymanova, G. T., Shikhaliyeva, I. M. & Bhattarai, A. (2020b). Acta Cryst. E76, 811–815. [DOI] [PMC free article] [PubMed]

[bb28] Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.

[bb29] Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.

[bb30] 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.

[bb31] 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.

[bb32] Shikhaliyev, N. Q., Çelikesir, S. T., Akkurt, M., Bagirova, K. N., Suleymanova, G. T. & Toze, F. A. A. (2019). Acta Cryst. E75, 465–469. [DOI] [PMC free article] [PubMed]

[bb33] 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.

[bb34] 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.

[bb35] Spackman, M. A. & McKinnon, J. J. (2002). CrystEngComm, 4, 378–392.

[bb36] Spackman, M. A., McKinnon, J. J. & Jayatilaka, D. (2008). CrystEngComm, 10, 377–388.

[bb37] Spek, A. L. (2020). Acta Cryst. E76, 1–11. [DOI] [PMC free article] [PubMed]

[bb38] 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.

[bb39] 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. [DOI] [PubMed]

PERMALINK

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

Namiq Q Shikhaliyev

Zeliha Atioğlu

Mehmet Akkurt

Ayten M Qacar

Rizvan K Askerov

Ajaya Bhattarai

Abstract

Chemical context

Structural commentary

Figure 1.

Supra­molecular features

Table 1. Hydrogen-bond geometry (Å, °).

Figure 2.

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

Figure 3.

Hirshfeld surface analysis

Figure 4.

Figure 5.

Figure 6.

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.

Database survey

Synthesis and crystallization

Refinement details

Table 4. Experimental details.

Supplementary Material

Acknowledgments

supplementary crystallographic information

Crystal data

Data collection

Refinement

Special details

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

Atomic displacement parameters (Å2)

Geometric parameters (Å, º)

Hydrogen-bond geometry (Å, º)

Funding Statement

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

RESOURCES

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Links to NCBI Databases

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

Supramolecular features

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

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.

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

Atomic displacement parameters (Å²)