Crystal structure and Hirshfeld surface analysis of a supra­molecular aggregate of 4-formyl-N,N-di­methyl­anilinium bromide with tetra­bromomethane

Gurbanov, A.V.; Hökelek, T.; Mammadova, G.Z.; Hasanov, K.I.; Javadzade, T.A.; Belay, A.N.

doi:10.1107/S2056989025006929

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 81| Part 9| September 2025| Pages 806-810

https://doi.org/10.1107/S2056989025006929

Open

access

Crystal structure and Hirshfeld surface analysis of a supramolecular aggregate of 4-formyl-N,N-dimethylanilinium bromide with tetrabromomethane

Atash V. Gurbanov,^a Tuncer Hökelek,^b Gunay Z. Mammadova,^c Khudayar I. Hasanov,^d Tahir A. Javadzade ^e and Alebel N. Belay ^f ^*

^aExcellence Center, Baku State University, Z. Khalilov Str. 23, AZ 1148 Baku, Azerbaijan, ^bHacettepe University, Department of Physics, 06800 Beytepe-Ankara, Türkiye, ^cDepartment of Chemistry, Baku State University, Z. Khalilov Str. 23, AZ 1148 Baku, Azerbaijan, ^dAzerbaijan Medical University, Scientific Research Centre (SRC), A. Kasumzade Str. 14, AZ 1022 Baku, Azerbaijan, ^eDepartment of Chemistry and Chemical Engineering, Khazar University, Mahsati Str. 41, AZ 1096 Baku, Azerbaijan, and ^fDepartment of Chemistry, Bahir Dar University, PO Box 79, Bahir Dar, Ethiopia
^*Correspondence e-mail: [email protected]

Edited by S. Parkin, University of Kentucky, USA (Received 22 July 2025; accepted 1 August 2025; online 7 August 2025)

The title compound, C₉H₁₂NO⁺·Br⁻·CBr₄, consists of one 4-formyl-N,N-dimethylbenzenaminium bromide and a tetrabromomethane molecule. In the crystal, the bromide ions link 4-formyl-N,N-dimethylbenzenaminium moieties through intermolecular C—H⋯Br and N—H⋯Br hydrogen bonds, while intermolecular C—H⋯O hydrogen bonds link 4-formyl-N,N-dimethylbenzenaminium cations, enclosing R²₂(18) ring motifs, into a di-periodic network structure. The tetrabromomethane molecules fill the spaces between the layers. Neither π–π nor C—H⋯π(ring) interactions are observed. A Hirshfeld surface analysis of the crystal structure indicates that the most abundant contacts contributing to the crystal packing are from H⋯Br/Br⋯H (56.0%), Br⋯Br (12.1%), H⋯O/O⋯H (9.7%) and H⋯H (9.5%) interactions.

Keywords: crystal structure; non-covalent interactions; hydrogen bond; benzenaminium.

CCDC reference: 2477918

1. Chemical context

Aldehydes are versatile compounds for the synthesis of organic acids, dyes, drugs, perfumes, detergents, soaps, etc. In the synthesis of those compounds the aldehydes undergo many different nucleophilic addition reactions. In order to increase the electrophilicity of the carbon atom at the C=O group of the aldehyde molecule, metal complexes or organocatalysts are commonly used (Ma et al., 2017 , 2021 ; Mahmudov & Pombeiro, 2023 ). Following crystal engineering principles (Gurbanov et al., 2020 ; Mahmoudi et al., 2018 ; Velásquez et al., 2019 ), weak interactions, halogen bonds, and other interactions, have been used in the activation of aldehydes towards the synthesis of various classes of organic compounds (Gurbanov et al., 2022 ; Sutar & Huber, 2019 ). We found that weak interactions can be formed with substituents at the aldehyde molecules instead of with the oxygen atom of the C=O group.

Herein, we provide details of the synthesis and an examination of the molecular and crystal structures, together with a Hirshfeld surface analysis, of the title compound (I).

2. Structural commentary

The title compound, (I), consists of one 4-formyl-N,N-dimethylbenzenaminium bromide unit and a tetrabromomethane solvent molecule (Fig. 1). The C—C and C—C—C bond lengths and angles of ring A are in the ranges 1.366 (7) to 1.3998 (10) Å and 118.6 (4) to 121.8 (4)° with average values of 1.388 (8) Å and 120.0 (4)°, respectively. These values are reported as 1.375 Å and 119.9° in p-dimethylamino-benzaldehyde hydrobromide, (II) (Dattagupta & Saha, 1973 ). Both of the N—C bonds between the methyl carbon and amino nitrogen atoms are 1.497 (4) Å, and the corresponding ones in compound (II) are 1.51 (4) and 1.43 (4) Å. The C=O bond length in the aldehyde group is 1.198 (7) Å, and its corresponding value is 1.18 (4) Å in compound (II). The dihedral angle between ring A and the plane of atoms (O1/C4/C8) is 0.00 (2)° while the corresponding value in compound (II) is 1.39°. The C4—C8 [1.467 (7) Å] bond length is in good agreement with the theoretically calculated single-bond lengths between trigonally linked (sp²) carbon atoms: 1.479 Å (Dewar & Schmeising, 1959 ) and 1.477 Å (Cruickshank & Sparks, 1960 ). The corresponding exocyclic C—C bond length is reported as 1.38 (4) Å in compound (II).

Figure 1
The title compound with atom-numbering scheme and 50% probability ellipsoids. Symmetry codes: (i) x, −y + $[{1\over 2}]$ , z; (ii) x, −y + $[{3\over 2}]$ , z.

3. Supramolecular features

In the crystal, intermolecular C—H⋯Br and N—H⋯Br hydrogen bonds link the bromide ions and the 4-formyl-N,N-dimethylbenzenaminium moieties (Table 1 and Fig. 2a). At the same time, intermolecular C—H⋯O hydrogen bonds (Table 1) link pairs of molecules through R₂²(18) hydrogen-bonding motifs, into a di-periodic network structure (Fig. 2a). The tetrabromomethane solvent molecules occupy the spaces between the layers (Fig. 2b).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Br4	0.85	2.37	3.221 (4)	175
C6—H6A⋯Br4	0.95	2.91	3.698 (4)	141
C7—H7A⋯O1ⁱⁱⁱ	0.98	2.52	3.424 (5)	153
C7—H7B⋯O1^iv	0.98	2.47	3.390 (5)	157
Symmetry codes: (iii) ; (iv) .

Figure 2
(a) A partial packing diagram showing the presence of an R₂²(18) ring motif (upper right). (b) A packing diagram viewed approximately down the c-axis direction. Intermolecular C—H⋯Br, N—H⋯Br and C—H⋯O hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonds have been omitted for clarity.

4. Hirshfeld surface analysis

For visualizing the intermolecular interactions in (I) a Hirshfeld surface (HS) analysis (Hirshfeld, 1977 ; Spackman & Jayatilaka, 2009 ) was carried out using Crystal Explorer 17.5 (Spackman et al., 2021 ). In the HS plotted over d_norm (Fig. 3), the white regions indicate contacts with distances equal to the sum of van der Waals radii, while the red and blue colours indicate distances shorter (in close contact) or longer (distant contact) than the sum of the van der Waals radii, respectively (Venkatesan et al., 2016 ), where the bright-red spots indicate their roles as the respective donors and/or acceptors. There are no π–π stacking interactions between aromatic rings in the packing of (I). Unusually, this is in spite of the presence of juxtaposed red/blue triangular regions in the HS plotted over shape-index (Fig. 4). There are also no C—H⋯π close contacts. According to the two-dimensional fingerprint plots (McKinnon et al., 2007 ), the intermolecular H⋯Br/Br⋯H, Br⋯Br, H⋯O/O⋯H, H⋯H and H⋯C/C⋯H contacts make the most abundant contributions to the HS of 56%, 12.1%, 9.7%, 9.5% and 7.5% respectively (Table 2, Fig. 5). All other contact types contribute <5% to the surface. The nearest neighbour coordination environment of a molecule can be determined from the colour patches on the HS based on how close to other molecules they are. These are plotted onto the HS for the H⋯Br/Br⋯H, Br⋯Br, H⋯O/O⋯H and H⋯H interactions in Fig. 6, showing that van der Waals interactions and hydrogen bonding play the major roles in the crystal packing (Hathwar et al., 2015 ).

Table 2
Selected interatomic distances (Å)

Br3⋯Br4ⁱ	3.3403 (8)	H7B⋯O1^iv	2.47
H6A⋯Br3ⁱⁱ	2.95	C2⋯H7C	2.83
O1⋯H5A	2.57	C7⋯H2A	2.96
H7A⋯O1ⁱⁱⁱ	2.52	H1N⋯H6A	2.22
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) ; (iv) .

Figure 3
View of the three-dimensional Hirshfeld surface plotted over d_norm.

Figure 4
Hirshfeld surface of the title compound plotted over shape-index.

Figure 5
Two-dimensional HS-fingerprint plots showing, (a) all interactions, and those delineated into (b)H⋯Br/Br⋯H, (c) Br⋯Br, (d) H⋯O/O⋯H, (e) H⋯H, (f) H⋯C/C⋯H interactions. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.

Figure 6
The Hirshfeld surface representations plotted as fragment patches for (a) H⋯Br/Br⋯H, (b) Br⋯Br, (c) H⋯O/O⋯H and (d) H⋯H interactions.

5. Database survey

A substructure search of the Cambridge Structural Database [CSD Version 5.46 (November 2024); Groom, et al., 2016 ] using the 4-formyl-N,N-dimethylanilinium moiety was carried out, and 49 similar compounds were found. Of these compounds, seven are structurally related. These include: p-dimethylamino-benzaldehyde hydrobromide, C₉H₁₂NOBr (CSD refcode MABZAL10; Dattagupta & Saha, 1973), 4-formyl-N,N-dimethylanilinium 4-methylbenzenesulfonate monohydrate, C₉H₁₂NO⁺·C₇H₇O₃S⁻·H₂O (CSD refcode QAFROH; Jin et al., 2016a ), ammonium 4-formyl-N,N-dimethylanilinium naphthalene-1,5-disulfonate ammonia, C₉H₁₂NO⁺·C₁₀H₆O₆S₂²⁻·H₄N⁺·H₃N (CSD refcode SUYYUI; Jin et al., 2016b ), 4-formyl-N,N-dimethylanilinium tetrafluoroborate, C₉H₁₂NO⁺·BF₄⁻ (CSD refcode VOJMEO; Froschauer et al., 2013 ) and 4-formyl-N,N-dimethylanilinium 2,4,6-trinitrophenolate, C₉H₁₂NO⁺·C₆H₂N₃O₇⁻ (CSD refcodes VUWLIJ: Thakuria et al., 2007 ; VUWLIJ01: Jin et al., 2016a; VUWLIJ02: Prasad, 2016 ). It is worth mentioning that the last three entries report different colours for the crystals (brown, colourless and metallic dark red).

6. Synthesis and crystallization

4-(Dimethylamino)benzaldehyde (5 mmol) and tetrabromomethane (5 mmol) were dissolved in 25 ml of CHBr₃, and left for slow evaporation. Orange crystals (suitable for X-ray analysis) of the product started to form after 1 d at room temperature; they were then filtered off and dried in air. Yield 59% (based on tetrabromomethane), orange powder soluble in methanol, ethanol and DMSO. Analysis calculated for C₁₀H₁₂Br₅NO (M_r = 561.73): C, 21.38; H, 2.15; N, 2.49. Found: C, 21.36; H, 2.13; N, 2.47. ¹H NMR (DMSO-d⁶), δ: 5.13 (–NHMe₂), 9.67 (CHO), 7.70 and 7.68 (2H Ar), 6.80 and 6.78 (2H Ar), 3.05 (6H, 2CH₃). ¹³C NMR (DMSO-d⁶), −29.2 (CBr₄), 43.6 (2CH₃), 111.2 (2C_Ar), 124.4 (CCHO), 133.6 (2C_Ar), 155.1 (CNMe₂), 190.0 (C=O).

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The N- and C-bound hydrogen-atom positions were calculated geometrically at distances of 0.85 Å (for NH), 0.95 Å (for CH) and 0.98 Å (for CH₃) and refined using a riding model by applying the constraint U_iso = kU_eq (C, N), where k = 1.2 for NH and CH hydrogen atoms and k = 1.5 for CH₃ hydrogen atoms.

Table 3
Experimental details

Crystal data
Chemical formula	C₉H₁₂NO⁺·Br⁻·CBr₄
M_r	561.76
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	150
a, b, c (Å)	21.1900 (7), 7.4114 (2), 10.2297 (4)
V (Å³)	1606.55 (9)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	12.49
Crystal size (mm)	0.32 × 0.18 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.086, 0.254
No. of measured, independent and observed [I > 2σ(I)] reflections	9073, 1649, 1462
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.611

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.064, 1.06
No. of reflections	1649
No. of parameters	98
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.79, −1.21
Computer programs: APEX3 and SAINT (Bruker, 2014 ), SHELXT2019/1 (Sheldrick, 2015a ), SHELXL2019/1 (Sheldrick, 2015b ) and SHELXTL (Sheldrick, 2008 ).

Supporting information

CCDC reference: 2477918

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989025006929/pk2717sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025006929/pk2717Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989025006929/pk2717Isup3.cml

checkCIF report

Computing details top

4-Formyl-N,N-dimethylanilinium bromide–tetrabromomethane (1/1) top

Crystal data top

C₉H₁₂NO⁺·Br⁻·CBr₄	D_x = 2.323 Mg m⁻³
M_r = 561.76	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 4744 reflections
a = 21.1900 (7) Å	θ = 2.8–25.7°
b = 7.4114 (2) Å	µ = 12.49 mm⁻¹
c = 10.2297 (4) Å	T = 150 K
V = 1606.55 (9) Å³	Plate, orange
Z = 4	0.32 × 0.18 × 0.12 mm
F(000) = 1048

Data collection top

Bruker APEXII CCD diffractometer	1462 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.027
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 25.7°, θ_min = 2.8°
T_min = 0.086, T_max = 0.254	h = −25→25
9073 measured reflections	k = −9→8
1649 independent reflections	l = −11→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.026	Hydrogen site location: mixed
wR(F²) = 0.064	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0299P)² + 4.3541P] where P = (F_o² + 2F_c²)/3
1649 reflections	(Δ/σ)_max = 0.001
98 parameters	Δρ_max = 0.79 e Å⁻³
6 restraints	Δρ_min = −1.21 e Å⁻³

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.

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

	x	y	z	U_iso*/U_eq
Br1	0.27771 (2)	0.53801 (5)	0.91970 (4)	0.02322 (12)
Br2	0.16582 (3)	0.750000	0.78589 (6)	0.03084 (16)
Br3	0.17920 (2)	0.750000	1.09645 (6)	0.02633 (15)
Br4	0.39332 (2)	0.250000	0.88637 (6)	0.02293 (15)
O1	0.53538 (19)	0.250000	0.1926 (4)	0.0295 (9)
N1	0.54209 (18)	0.250000	0.8217 (4)	0.0160 (9)
H1N	0.502359	0.250000	0.833231	0.019*
C1	0.55221 (17)	0.250000	0.6801 (5)	0.0158 (10)
C2	0.61354 (18)	0.250000	0.6293 (5)	0.0219 (11)
H2A	0.649120	0.250000	0.685839	0.026*
C3	0.6211 (2)	0.250000	0.4967 (5)	0.0244 (12)
H3A	0.662508	0.250000	0.460938	0.029*
C4	0.5690 (2)	0.250000	0.4127 (5)	0.0195 (11)
C5	0.5087 (2)	0.250000	0.4645 (4)	0.0247 (12)
H5A	0.473132	0.250000	0.407806	0.030*
C6	0.4998 (2)	0.250000	0.6000 (4)	0.0227 (12)
H6A	0.458558	0.250000	0.636234	0.027*
C7	0.56696 (17)	0.4161 (5)	0.8872 (3)	0.0201 (8)
H7A	0.556697	0.412102	0.980521	0.030*
H7B	0.547604	0.523040	0.847635	0.030*
H7C	0.612859	0.421721	0.876162	0.030*
C8	0.5776 (3)	0.250000	0.2704 (5)	0.0268 (13)
H8A	0.619581	0.250000	0.237724	0.032*
C9	0.2245 (2)	0.750000	0.9317 (5)	0.0193 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01931 (18)	0.0224 (2)	0.0280 (2)	0.00397 (14)	0.00079 (15)	0.00030 (15)
Br2	0.0245 (3)	0.0342 (3)	0.0338 (4)	0.000	−0.0135 (2)	0.000
Br3	0.0197 (3)	0.0320 (3)	0.0273 (3)	0.000	0.0072 (2)	0.000
Br4	0.0177 (2)	0.0244 (3)	0.0266 (3)	0.000	0.0002 (2)	0.000
O1	0.039 (2)	0.038 (2)	0.012 (2)	0.000	−0.0011 (18)	0.000
N1	0.0140 (19)	0.024 (2)	0.010 (2)	0.000	−0.0006 (16)	0.000
C1	0.015 (2)	0.020 (2)	0.012 (3)	0.000	0.0019 (19)	0.000
C2	0.013 (2)	0.036 (3)	0.016 (3)	0.000	−0.002 (2)	0.000
C3	0.013 (2)	0.038 (3)	0.022 (3)	0.000	0.006 (2)	0.000
C4	0.021 (2)	0.025 (3)	0.013 (3)	0.000	0.002 (2)	0.000
C5	0.022 (3)	0.042 (3)	0.011 (3)	0.000	−0.003 (2)	0.000
C6	0.014 (2)	0.041 (3)	0.013 (3)	0.000	0.000 (2)	0.000
C7	0.0262 (17)	0.0209 (19)	0.0132 (19)	−0.0021 (15)	−0.0019 (15)	−0.0029 (15)
C8	0.027 (3)	0.036 (3)	0.018 (3)	0.000	0.008 (2)	0.000
C9	0.013 (2)	0.022 (3)	0.022 (3)	0.000	0.001 (2)	0.000

Geometric parameters (Å, º) top

Br1—C9	1.937 (3)	C3—C4	1.3998 (10)
Br2—C9	1.942 (5)	C3—H3A	0.9500
Br3—C9	1.940 (5)	C4—C5	1.384 (7)
O1—C8	1.198 (7)	C4—C8	1.467 (7)
N1—C1	1.464 (6)	C5—C6	1.3995 (10)
N1—C7ⁱ	1.497 (4)	C5—H5A	0.9500
N1—C7	1.497 (4)	C6—H6A	0.9500
N1—H1N	0.8501	C7—H7A	0.9800
C1—C6	1.379 (6)	C7—H7B	0.9800
C1—C2	1.3997 (10)	C7—H7C	0.9800
C2—C3	1.366 (7)	C8—H8A	0.9500
C2—H2A	0.9500

Br3···Br4ⁱⁱ	3.3403 (8)	H7B···O1^v	2.47
H6A···Br3ⁱⁱⁱ	2.95	C2···H7C	2.83
O1···H5A	2.57	C7···H2A	2.96
H7A···O1^iv	2.52	H1N···H6A	2.22

C1—N1—C7ⁱ	113.0 (2)	C6—C5—H5A	119.9
C1—N1—C7	113.0 (2)	C1—C6—C5	118.8 (4)
C7ⁱ—N1—C7	110.6 (4)	C1—C6—H6A	120.6
C1—N1—H1N	106.4	C5—C6—H6A	120.6
C7ⁱ—N1—H1N	106.7	N1—C7—H7A	109.5
C7—N1—H1N	106.6	N1—C7—H7B	109.5
C6—C1—C2	121.8 (4)	H7A—C7—H7B	109.5
C6—C1—N1	118.0 (3)	N1—C7—H7C	109.5
C2—C1—N1	120.2 (4)	H7A—C7—H7C	109.5
C3—C2—C1	118.6 (4)	H7B—C7—H7C	109.5
C3—C2—H2A	120.7	O1—C8—C4	124.5 (5)
C1—C2—H2A	120.7	O1—C8—H8A	117.7
C2—C3—C4	121.1 (4)	C4—C8—H8A	117.7
C2—C3—H3A	119.4	Br1—C9—Br1^vi	108.4 (2)
C4—C3—H3A	119.4	Br1—C9—Br3	110.07 (18)
C5—C4—C3	119.6 (4)	Br1^vi—C9—Br3	110.07 (18)
C5—C4—C8	119.6 (4)	Br1—C9—Br2	108.90 (18)
C3—C4—C8	120.8 (5)	Br1^vi—C9—Br2	108.90 (18)
C4—C5—C6	120.2 (4)	Br3—C9—Br2	110.5 (2)
C4—C5—H5A	119.9

C7ⁱ—N1—C1—C6	116.7 (3)	C2—C3—C4—C8	180.000 (1)
C7—N1—C1—C6	−116.7 (3)	C3—C4—C5—C6	0.000 (1)
C7ⁱ—N1—C1—C2	−63.3 (3)	C8—C4—C5—C6	180.000 (1)
C7—N1—C1—C2	63.3 (3)	C2—C1—C6—C5	0.000 (1)
C6—C1—C2—C3	0.000 (1)	N1—C1—C6—C5	180.000 (1)
N1—C1—C2—C3	180.000 (1)	C4—C5—C6—C1	0.000 (1)
C1—C2—C3—C4	0.000 (1)	C5—C4—C8—O1	0.000 (1)
C2—C3—C4—C5	0.000 (1)	C3—C4—C8—O1	180.000 (1)

Symmetry codes: (i) x, −y+1/2, z; (ii) −x+1/2, −y+1, z+1/2; (iii) −x+1/2, y−1/2, z−1/2; (iv) x, y, z+1; (v) −x+1, −y+1, −z+1; (vi) x, −y+3/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Br4	0.85	2.37	3.221 (4)	175
C6—H6A···Br4	0.95	2.91	3.698 (4)	141
C7—H7A···O1^iv	0.98	2.52	3.424 (5)	153
C7—H7B···O1^v	0.98	2.47	3.390 (5)	157

Symmetry codes: (iv) x, y, z+1; (v) −x+1, −y+1, −z+1.

Acknowledgements

This work has been supported by the Baku State University, Azerbaijan Medical University and Khazar University. TH is also grateful to Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004). The authors' contributions are as follows. Conceptualization, AVG, TH and ANB; synthesis, AVG and GZM; X-ray analysis, AVG; writing (review and editing of the manuscript) AVG and TH; funding acquisition, AVG, GZM, KIH and TAJ; supervision, AVG, TH and ANB.

References

Bruker (2014). APEX3 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cruickshank, D. W. J. & Sparks, R. A. (1960). Proc. Roy. Soc. A258, 270–285. Google Scholar
Dattagupta, J. K. & Saha, N. N. (1973). Acta Cryst. B29, 1228–1233. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Dewar, M. J. S. & Schmeising, H. N. (1959). Tetrahedron 5, 166–178. CrossRef CAS Web of Science Google Scholar
Froschauer, C., Weber, H. K., Kahlenberg, V., Laus, G. & Schottenberger, H. (2013). Crystals 3, 248–256. Web of Science CSD CrossRef CAS 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., Karmakar, A., Aliyeva, V. A., Mahmudov, K. T. & Pombeiro, A. J. L. (2022). Dalton Trans. 51, 1019–1031. Web of Science CSD CrossRef CAS PubMed Google Scholar
Gurbanov, A. V., Kuznetsov, M. L., Mahmudov, K. T., Pombeiro, A. J. L. & Resnati, G. (2020). Chem. A Eur. J. 26, 14833–14837. Web of Science CSD CrossRef CAS Google Scholar
Hathwar, V. R., Sist, M., Jørgensen, M. R. V., Mamakhel, A. H., Wang, X., Hoffmann, C. M., Sugimoto, K., Overgaard, J. & Iversen, B. B. (2015). IUCrJ 2, 563–574. Web of Science CSD CrossRef CAS PubMed IUCr Journals Google Scholar
Hirshfeld, H. L. (1977). Theor. Chim. Acta 44, 129–138. CrossRef CAS Web of Science Google Scholar
Jin, S., Wang, L., Liu, H., Liu, L., Zhang, H., Wang, D., Li, M., Guo, J. & Guo, M. (2016a). J. Mol. Struct. 1116, 155–164. Web of Science CSD CrossRef CAS Google Scholar
Jin, S., Wang, L., Lou, Y., Liu, L., Li, B., Li, L., Feng, C., Liu, H. & Wang, D. (2016b). J. Mol. Struct. 1108, 735–747. Web of Science CSD 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., Sutradhar, M., Kopylovich, M. N., Mahmudov, K. T., Maharramov, A. M., Guseinov, F. I., Zubkov, F. I. & Pombeiro, A. J. L. (2017). J. Mol. Catal. 428, 17–23. 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
Mahmoudi, G., Afkhami, F. A., Castiñeiras, A., García-Santos, I., Gurbanov, A. V., Zubkov, F. I., Mitoraj, M. P., Kukułka, M., Sagan, F., Szczepanik, D. W., Konyaeva, I. A. & Safin, D. A. (2018). Inorg. Chem. 57, 4395–4408. Web of Science CSD CrossRef CAS PubMed Google Scholar
Mahmudov, K. T. & Pombeiro, A. J. L. (2023). Chem. A Eur. J. 29, e202203861. Web of Science CrossRef Google Scholar
McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814–3816. Web of Science CrossRef Google Scholar
Prasad, A. A. (2016). CSD Communication (Refcode VUWLIJ02). CCDC, Cambridge, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS 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
Spackman, M. A. & Jayatilaka, D. (2009). CrystEngComm 11, 19–32. Web of Science CrossRef CAS Google Scholar
Spackman, P. R., Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Jayatilaka, D. & Spackman, M. A. (2021). J. Appl. Cryst. 54, 1006–1011. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sutar, R. L. & Huber, S. M. (2019). ACS Catal. 9, 9622–9639. Web of Science CrossRef CAS Google Scholar
Thakuria, H., Borah, B. M., Pramanik, A. & Das, G. (2007). J. Chem. Crystallogr. 37, 807–816. Web of Science CSD CrossRef CAS Google Scholar
Velásquez, J. D., Mahmoudi, G., Zangrando, E., Gurbanov, A. V., Zubkov, F. I., Zorlu, Y., Masoudiasl, A. & Echeverría, J. (2019). CrystEngComm 21, 6018–6025. Google Scholar
Venkatesan, P., Thamotharan, S., Ilangovan, A., Liang, H. & Sundius, T. (2016). Spectrochim. Acta A Mol. Biomol. Spectrosc. 153, 625–636. Web of Science CSD 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.