Synthesis, crystal structure and Hirshfeld surface analysis of a zinc(II) coordination polymer of 5-phenyl-1,3,4-oxa­diazole-2-thiol­ate

Pirimova, M.; Torambetov, B.; Kadirova, S.; Ziyaev, A.; Gonnade, R.G.; Ashurov, J.

doi:10.1107/S2056989022006922

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 78| Part 8| August 2022| Pages 794-797

https://doi.org/10.1107/S2056989022006922

Open

access

Synthesis, crystal structure and Hirshfeld surface analysis of a zinc(II) coordination polymer of 5-phenyl-1,3,4-oxadiazole-2-thiolate

Mehribon Pirimova,^a Batirbay Torambetov,^a ^* Shakhnoza Kadirova,^a Abdukhakim Ziyaev,^b Rajesh G Gonnade ^c and Jamshid Ashurov ^d

^aNational University of Uzbekistan named after Mirzo Ulugbek, 4 University St, Tashkent, 100174, Uzbekistan, ^bS. Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Mirzo Ulugbek Str. 77, 100170, Tashkent, Uzbekistan, ^cPhysical and Materials Chemistry Division, CSIR-National Chemical Laboratory, Pune-411008, India, and ^dInstitute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, M. Ulugbek Str, 83, Tashkent, 100125, Uzbekistan
^*Correspondence e-mail: torambetov_b@mail.ru

Edited by G. Diaz de Delgado, Universidad de Los Andes, Venezuela (Received 15 June 2022; accepted 6 July 2022; online 14 July 2022)

A new zinc coordination polymer with 5-phenyl-1,3,4-oxadiazole-2-thiolate, namely, catena-poly[zinc(II)-bis(μ₂-5-phenyl-1,3,4-oxadiazole-2-thiolato)-κ²N³:S;κ²S:N³], [Zn(C₈H₅N₂OS)₂]_n, was synthesized. The single-crystal X-ray diffraction analysis shows that the polymeric structure crystallizes in the centrosymmetric monoclinic C2/c space group. The Zn^II atom is coordinated to two S and two N atoms from four crystallographically independent (L) ligands, forming zigzag chains along the [001] direction. This polymer complex forms an eight-membered [Zn–S–C–N–Zn–S–C–N] chair-like ring with two Zn^II atoms and two ligand molecules. On the Hirshfeld surface, the largest contributions come from the short contacts such as van der Waals forces, including H⋯H, C⋯H and S⋯H. Interactions including N⋯H, O⋯H and C⋯C contacts were also observed; however, their contribution to the overall stability of the crystal lattice is minor.

Keywords: crystal structure; zinc complex; 5-phenyl-1,3,4-oxadiazole-2-thiol; coordination polymer; Hirshfeld surface analysis.

CCDC reference: 2184492

1. Chemical context

Among heterocyclic organic compounds, 1,3,4-oxadiazoles have become an important class of heterocycles because of their broad spectrum of biological activity (De Oliveira et al., 2012 ; Vaidya et al., 2020 ). Scientists have identified many properties of 1,3,4-oxadiazole derivatives, such as antimicrobial (Bala et al., 2014 ; Zachariah et al., 2015 ; Ahmed et al., 2017 ; Razzoqova et al., 2019 ), antituberculosis (Makane et al., 2019 ; Wang et al., 2022 ), anticancer (Alam, 2022 ; Vaidya et al., 2020; Zhang et al., 2005 ), anti-inflammatory (Abd-Ellah et al., 2017 ), analgesic (Husain & Ajmal, 2009 ), herbicidal (Sun et al., 2014 ; Duan et al., 2011 ) and antifungal (Zhang et al., 2013 ; Capoci et al., 2019 ) activities. Heterocyclic thiones are an important type of compound in coordination chemistry because of their potential multifunctional donor sites, namely either exocyclic sulfur or endocyclic nitrogen (Reddy et al., 2011 ; Wang et al., 2010 ). The presence of the 1,3,4-oxadiazole ring affects the physicochemical and pharmacokinetic properties of the entire compound. An exciting feature of these metal complexes is that they can be mononuclear (Singh et al., 2008 ; Ouilia et al., 2012 ), binuclear (Xiao et al., 2011 ; Wang et al., 2007 ) and/or polymeric (Beghidja et al., 2007 ).

Oxadiazole ligands are ideal objects for creating new coordination compounds with great potential in various fields. Scientists have written extensive literature on the biological properties of oxadiazole-based complex compounds, especially on their anticancer effects. In addition to these, in the field of electrical engineering, metal complexes bearing oxadiazole ligands have been used as emitting particles in light-emitting diodes. The introduction of various functionalized oxadiazole ligands makes it easy to control the emission color, thermal stability, and film-forming properties of such complexes (Salassa & Terenzi, 2019 ).

Herein, we report on the synthesis and crystal structure of a new polymeric complex, [ZnL₂]_n, with L = 5-phenyl-1,3,4-oxadiazole-2-thiol.

2. Structural commentary

The single crystal X-ray structure of 5-phenyl-1,3,4-oxadiazole-2-thiolate Zn^II shows a polymeric structure that crystallizes in the centrosymmetric monoclinic space group C2/c (Table 2). As seen in Fig. 1, its asymmetric unit contains half a zinc atom and one ligand anion. The central Zn^II atom has a distorted tetrahedral environment comprising two sulfur and two nitrogen atoms. It is coordinated by four crystallographically independent (L) ligands, forming zigzag chains along the [001] direction, which are linked by two sulfur atoms and two nitrogen atoms of four ligands. The Zn1—S1 and Zn1—N1 bond lengths are 2.3370 (5) Å, 2.0184 (14) Å, respectively. In this case, the bond angles of the atom forming the tetrahedral polyhedron are slightly different from the angles of the ideal tetrahedron [N1—Zn1–N1 = 111.37 (9)°, S1—Zn1—S1 = 100.46 (3)° and N1—Zn1—S1 = 108.51 (4)°]. It is known from the literature (Razzoqova et al., 2019) that the sulfur atom in the 1,3,4-oxadiazole-2-thione molecule is attached to the ring by a double bond. In this polymer complex synthesized based on Zn^II ion, the oxadiazole derivative transforms into the thiol tautomeric form and binds to the Zn ion. The N1 atom in the ligand molecule, on the other hand, forms a bond with another Zn^II ion due to its high electron-donating property, resulting in an eight-membered [Zn–S–C–N–Zn–S–C–N] chair-like ring with two Zn^II atoms and two ligand molecules (Fig. 2). The dihedral angle between the mean planes of the phenyl (C3–C8) and oxadiazole (C1/O1/C2/N2/N1) rings of the ligand molecule is 13.42 (8)°. The conformation of the oxadiazole-thiol fragment of the ligand is approximately planar (r.m.s. deviation 0.006 Å), with a maximum deviation from the least-squares plane of 0.009 (1) Å for atom O1. The dihedral angle between the planes of the two neighboring independent oxadiazole-thiol (C1/O1/C2/N2/N1/S1) fragments is 64.10 (9)°.

Table 2
Experimental details

Crystal data
Chemical formula	[Zn(C₈H₅N₂OS)₂]
M_r	419.79
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	20.4223 (3), 11.3260 (2), 7.4019 (1)
β (°)	98.310 (1)
V (Å³)	1694.11 (5)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	4.48
Crystal size (mm)	0.60 × 0.14 × 0.08

Data collection
Diffractometer	XtaLAB Synergy, single source at home/near, HyPix3000
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2020 $[Rigaku OD (2020). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.099, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7033, 1634, 1536
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.073, 1.09
No. of reflections	1634
No. of parameters	134
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.33
Computer programs: CrysAlis PRO (Rigaku OD, 2020 $[Rigaku OD (2020). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT2014/5 (Sheldrick, 2015a ), SHELXL2016/6 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Figure 1
The molecular structure of [Zn_0.5L] with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are displayed as small spheres of arbitrary radii.

Figure 2
The view of the molecular packing showing the polymeric chain extended along the c-axis.

3. Supramolecular features

The [(ZnL₂)_n] unit is given as a monomer of the polymeric chain that extends parallel to the c-axis. Along the polymeric chain, the hydrophilic groups are concentrated within the core of the chain while the phenyl rings project approximately normal to the chain. Neighboring chains across the ab plane are loosely connected via a rather weak C6—H6⋯S1 hydrogen bond (Table 1, Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯S1ⁱ	1.00 (3)	2.86 (3)	3.608 (2)	132 (2)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Figure 3
Crystal packing of the polymeric chains in the [(ZnL₂)_n] structure. The projection is along the [001] direction. Hydrogen bonds are shown by cyan lines.

4. Hirshfeld surface analysis

To further investigate the intermolecular interactions present in the title compound, a Hirshfeld surface analysis was performed, and the two-dimensional fingerprint plots were generated with CrystalExplorer17 (Turner et al., 2017 ). The Hirshfeld surface mapped over d_norm and corresponding colors representing various interactions are shown in Fig. 4. We chose the ZnL₂ molecular fragment as the monomer unit for calculating the Hirshfeld surface of this polymer complex.

Figure 4
Hirshfeld surfaces mapped over d_norm calculated for the monomer part of the polymer molecule.

The large red areas on the Hirshfeld surface correspond to the Zn⋯N interactions. The two-dimensional (2D) fingerprint plots (McKinnon et al., 2007 ) are shown in Fig. 5. On the Hirshfeld surface, the largest contributions (19.2%, 19.5% and 19%) come from short contacts such as van der Waals forces, H⋯H, C⋯H and S⋯H contacts. N⋯H (8.1%), O⋯H (8%) and C⋯C (4.7%) contacts are also observed. These interactions play a crucial role in the overall stabilization of the crystal packing.

Figure 5
Contributions of the various contacts to the fingerprint plot built using the Hirshfeld surface of the title compound.

5. Database survey

A survey of the Cambridge Structural Database (CSD, version 5.43, update of November 2021; Groom et al., 2016 ) revealed that crystal structures had been reported for complexes of 1,3,4-oxadiazole derivatives and a number of metal ions, including zinc, copper, nickel, manganese, cadmium, cobalt and silver. No polymer complexes containing [M–S–C–N–M–S–C–N] eight-membered cyclization have been reported. The structures of complexes of Pt, Sn and Au based on 5-phenyl-1,3,4-oxadiazole-2-thiole with additional ligands have been deposited in the CSD (FATNIZ, Al-Jibori et al., 2012 ; HAXTAC, Ma et al., 2005 ; and YIVVEG, Chaves et al., 2014 ). However, no complexes containing only the zinc ion and 5-phenyl-1,3,4-oxadiazole-2-thiolate have been documented in the CSD.

6. Synthesis and crystallization

ZnCl₂ (0.136 g, 0.001 mol) and 5-phenyl-1,3,4-oxadiazole-2-thiol (ligand) (0.354 g, 0.002 mol) were dissolved separately in ethanol (10 mL). To a solution of the ligand, an aqueous solution of KOH (0.112 g, 0.002 mol) was added. The obtained solutions were mixed together and stirred at 323 K for 20 min. A white precipitate was obtained. The precipitate was filtered and allowed to dry. The solid residue was dissolved in DMF to crystallize for the single crystal X-ray diffraction studies. X-ray quality single crystals were produced after 10 days by slow evaporation of the solution.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. All the hydrogen atoms were located in difference-Fourier maps and refined isotropically.

Supporting information

CCDC reference: 2184492

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989022006922/dj2049sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989022006922/dj2049Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2020); cell refinement: CrysAlis PRO (Rigaku OD, 2020); data reduction: CrysAlis PRO (Rigaku OD, 2020); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

catena-Poly[zinc(II)-bis(µ₂-5-phenyl-1,3,4-oxadiazole-2-thiolato)-κ²N³:S;κ²S: N³] top

Crystal data top

[Zn(C₈H₅N₂OS)₂]	F(000) = 848
M_r = 419.79	D_x = 1.646 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
a = 20.4223 (3) Å	Cell parameters from 5128 reflections
b = 11.3260 (2) Å	θ = 4.4–71.1°
c = 7.4019 (1) Å	µ = 4.48 mm⁻¹
β = 98.310 (1)°	T = 293 K
V = 1694.11 (5) Å³	Block, colourless
Z = 4	0.60 × 0.14 × 0.08 mm

Data collection top

XtaLAB Synergy, single source at home/near, HyPix3000 diffractometer	1634 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	1536 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.028
Detector resolution: 10.0000 pixels mm^-1	θ_max = 71.5°, θ_min = 4.4°
ω scans	h = −25→23
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2020)	k = −13→13
T_min = 0.099, T_max = 1.000	l = −9→8
7033 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.026	All H-atom parameters refined
wR(F²) = 0.073	w = 1/[σ²(F_o²) + (0.0425P)² + 0.6399P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
1634 reflections	Δρ_max = 0.26 e Å⁻³
134 parameters	Δρ_min = −0.33 e Å⁻³
0 restraints

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
Zn1	0.500000	0.42861 (3)	0.750000	0.03700 (13)
S1	0.52858 (2)	0.70338 (4)	0.49120 (6)	0.04489 (15)
O1	0.64980 (6)	0.66497 (11)	0.66937 (16)	0.0378 (3)
N1	0.57974 (7)	0.52907 (14)	0.7241 (2)	0.0381 (3)
N2	0.64167 (7)	0.49941 (14)	0.8226 (2)	0.0402 (3)
C2	0.68103 (8)	0.58151 (15)	0.7854 (2)	0.0360 (4)
C3	0.75171 (8)	0.59280 (16)	0.8505 (2)	0.0370 (4)
C1	0.58617 (8)	0.62555 (15)	0.6334 (2)	0.0362 (4)
C8	0.78515 (9)	0.49670 (18)	0.9351 (3)	0.0442 (4)
C4	0.78562 (10)	0.69688 (18)	0.8287 (3)	0.0472 (4)
C7	0.85194 (10)	0.5044 (2)	0.9992 (3)	0.0572 (5)
C5	0.85239 (11)	0.7043 (2)	0.8940 (3)	0.0578 (5)
C6	0.88524 (10)	0.6091 (2)	0.9798 (3)	0.0613 (6)
H8	0.7634 (11)	0.4299 (18)	0.946 (3)	0.042 (6)*
H5	0.8723 (13)	0.772 (3)	0.874 (3)	0.068 (7)*
H4	0.7642 (12)	0.761 (2)	0.771 (3)	0.059 (7)*
H7	0.8758 (14)	0.443 (2)	1.056 (4)	0.074 (8)*
H6	0.9339 (15)	0.614 (3)	1.020 (4)	0.088 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.02217 (18)	0.0460 (2)	0.0416 (2)	0.000	0.00048 (13)	0.000
S1	0.0363 (3)	0.0440 (3)	0.0508 (3)	0.00848 (17)	−0.00577 (19)	−0.00479 (18)
O1	0.0309 (6)	0.0384 (6)	0.0423 (6)	−0.0034 (5)	−0.0009 (5)	0.0004 (5)
N1	0.0228 (7)	0.0461 (8)	0.0440 (8)	−0.0019 (6)	0.0001 (6)	0.0003 (6)
N2	0.0243 (7)	0.0483 (8)	0.0462 (8)	−0.0030 (6)	−0.0012 (6)	0.0056 (6)
C2	0.0291 (8)	0.0410 (9)	0.0368 (8)	−0.0004 (6)	0.0010 (7)	−0.0010 (6)
C3	0.0276 (8)	0.0468 (9)	0.0359 (8)	−0.0050 (7)	0.0019 (6)	−0.0033 (7)
C1	0.0273 (8)	0.0418 (9)	0.0386 (8)	0.0008 (7)	0.0013 (6)	−0.0070 (7)
C8	0.0357 (9)	0.0498 (11)	0.0459 (9)	−0.0059 (8)	0.0012 (7)	0.0053 (8)
C4	0.0380 (10)	0.0446 (10)	0.0578 (11)	−0.0048 (8)	0.0027 (8)	0.0008 (9)
C7	0.0363 (10)	0.0697 (14)	0.0620 (12)	0.0004 (10)	−0.0044 (9)	0.0124 (11)
C5	0.0393 (11)	0.0591 (13)	0.0741 (14)	−0.0179 (9)	0.0052 (10)	−0.0027 (11)
C6	0.0288 (10)	0.0797 (15)	0.0722 (14)	−0.0108 (10)	−0.0035 (9)	0.0046 (12)

Geometric parameters (Å, º) top

Zn1—S1ⁱ	2.3370 (5)	C3—C8	1.385 (3)
Zn1—S1ⁱⁱ	2.3370 (5)	C3—C4	1.388 (3)
Zn1—N1	2.0184 (14)	C8—C7	1.381 (3)
Zn1—N1ⁱⁱⁱ	2.0184 (14)	C8—H8	0.89 (2)
S1—C1	1.7059 (17)	C4—C5	1.382 (3)
O1—C2	1.371 (2)	C4—H4	0.92 (3)
O1—C1	1.3635 (19)	C7—C6	1.384 (3)
N1—N2	1.4062 (18)	C7—H7	0.92 (3)
N1—C1	1.299 (2)	C5—C6	1.376 (4)
N2—C2	1.285 (2)	C5—H5	0.89 (3)
C2—C3	1.460 (2)	C6—H6	1.00 (3)

S1ⁱ—Zn1—S1ⁱⁱ	100.46 (3)	O1—C1—S1	120.26 (13)
N1—Zn1—S1ⁱⁱ	108.51 (4)	N1—C1—S1	129.90 (13)
N1—Zn1—S1ⁱ	113.82 (4)	N1—C1—O1	109.83 (14)
N1ⁱⁱⁱ—Zn1—S1ⁱ	108.50 (4)	C3—C8—H8	119.3 (14)
N1ⁱⁱⁱ—Zn1—S1ⁱⁱ	113.82 (5)	C7—C8—C3	120.24 (19)
N1—Zn1—N1ⁱⁱⁱ	111.37 (9)	C7—C8—H8	120.5 (14)
C1—S1—Zn1ⁱ	102.39 (6)	C3—C4—H4	120.8 (16)
C1—O1—C2	103.92 (13)	C5—C4—C3	119.6 (2)
N2—N1—Zn1	119.57 (11)	C5—C4—H4	119.6 (16)
C1—N1—Zn1	131.80 (12)	C8—C7—C6	119.6 (2)
C1—N1—N2	108.57 (13)	C8—C7—H7	122.8 (17)
C2—N2—N1	105.05 (14)	C6—C7—H7	117.6 (17)
O1—C2—C3	119.65 (15)	C4—C5—H5	116.4 (17)
N2—C2—O1	112.61 (14)	C6—C5—C4	120.3 (2)
N2—C2—C3	127.75 (16)	C6—C5—H5	123.3 (17)
C8—C3—C2	118.67 (16)	C7—C6—H6	119.8 (18)
C8—C3—C4	119.85 (17)	C5—C6—C7	120.33 (19)
C4—C3—C2	121.48 (17)	C5—C6—H6	119.8 (18)

Zn1ⁱ—S1—C1—O1	116.48 (12)	C2—O1—C1—S1	−179.75 (12)
Zn1ⁱ—S1—C1—N1	−65.24 (17)	C2—O1—C1—N1	1.66 (18)
Zn1—N1—N2—C2	−176.89 (12)	C2—C3—C8—C7	−179.66 (19)
Zn1—N1—C1—S1	−2.7 (3)	C2—C3—C4—C5	179.34 (19)
Zn1—N1—C1—O1	175.68 (11)	C3—C8—C7—C6	0.5 (3)
O1—C2—C3—C8	−166.60 (16)	C3—C4—C5—C6	0.2 (3)
O1—C2—C3—C4	13.2 (3)	C1—O1—C2—N2	−1.25 (19)
N1—N2—C2—O1	0.4 (2)	C1—O1—C2—C3	178.37 (15)
N1—N2—C2—C3	−179.19 (17)	C1—N1—N2—C2	0.68 (19)
N2—N1—C1—S1	−179.91 (13)	C8—C3—C4—C5	−0.9 (3)
N2—N1—C1—O1	−1.49 (19)	C8—C7—C6—C5	−1.2 (4)
N2—C2—C3—C8	13.0 (3)	C4—C3—C8—C7	0.6 (3)
N2—C2—C3—C4	−167.27 (19)	C4—C5—C6—C7	0.9 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···S1^iv	1.00 (3)	2.86 (3)	3.608 (2)	132 (2)

Symmetry code: (iv) x+1/2, −y+3/2, z+1/2.

Funding information

This work was supported by Uzbekistan Ministry of Innovation Development.

References

Abd-Ellah, H. S., Abdel-Aziz, M., Shoman, M. E., Beshr, E. A. M., Kaoud, T. S. & Ahmed, A. F. F. (2017). Bioorg. Chem. 74, 15–29. Web of Science CAS PubMed Google Scholar
Ahmed, M. N., Yasin, K. A., Hameed, S., Ayub, K., Haq, I., Tahir, M. N. & Mahmood, T. (2017). J. Mol. Struct. 1129, 50–59. Web of Science CrossRef CAS Google Scholar
Alam, M. M. (2022). Biointerface Res. Appl. Chem. 12, 5727–5744. CAS Google Scholar
Al-Jibori, S. A., Khaleel, T. F., Ahmed, S. A. O., Al-Hayaly, L. J., Merzweiler, K., Wagner, C. & Hogarth, G. (2012). Polyhedron, 41, 20–24. CAS Google Scholar
Bala, S., Kamboj, S., Kajal, A., Saini, V. & Prasad, D. N. (2014). BioMed Res. Int. 172791. Google Scholar
Beghidja, C., Rogez, G. & Welter, R. (2007). New J. Chem. 31, 1403–1406. Web of Science CSD CrossRef CAS Google Scholar
Capoci, I. R. G., Sakita, K. M., Faria, D. R., Rodrigues-Vendramini, F. A. V., Arita, G. S., de Oliveira, A. G. & Svidzinski, T. I. E. (2019). Front. Microbiol. 10, 1–11. Web of Science CrossRef PubMed Google Scholar
Chaves, J. D. S., Neumann, F., Francisco, T. M., Corrêa, C. C., Lopes, M. T. P., Silva, H., Fontes, A. P. S. & de Almeida, M. V. (2014). Inorg. Chim. Acta, 414, 85–90. Web of Science CrossRef CAS Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Duan, W.-G., Li, X.-R., Mo, Q.-J., Huang, J.-X., Cen, B., Xu, X.-T. & Lei, F.-H. (2011). Holzforschung, 65, 191–197. Web of Science CrossRef 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
Husain, A. & Ajmal, M. (2009). Acta Pharm. 59, 223–233. Web of Science CrossRef PubMed CAS Google Scholar
Ma, C.-L., Tian, G.-R. & Zhang, R.-F. (2005). Polyhedron, 24, 1773–1780. Web of Science CrossRef CAS Google Scholar
Makane, V. B., Krishna, V. S., Krishna, E. V., Shukla, M., Mahizhaveni, B., Misra, S., Chopra, S., Sriram, D., Azger Dusthackeer, V. N. & Rode, H. B. (2019). Future Med. Chem. 11, 499–510. 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
Oliveira, C. S. de, Lira, B. F., Barbosa-Filho, J. M., Lorenzo, J. G. F. & de Athayde-Filho, P. F. (2012). Molecules, 17, 10192–10231. Web of Science PubMed Google Scholar
Ouilia, S., Beghidja, C., Beghidja, A. & Michaud, F. (2012). Acta Cryst. E68, m943. CrossRef IUCr Journals Google Scholar
Razzoqova, S. R., Kadirova, S., Ashurov, J. M., Rakhmonova, D. S., Ziyaev, A. & Parpiev, N. A. (2019). IUCrData, 4, x191532. Google Scholar
Reddy, M. A., Mallesham, G., Thomas, A., Srinivas, K., Rao, V. J., Bhanuprakash, K., Giribabu, L., Grover, R., Kumar, A., Kamalasanan, M. N. & Srivastava, R. (2011). Synth. Met. 161, 869–880. Web of Science CrossRef CAS Google Scholar
Rigaku OD (2020). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England. Google Scholar
Salassa, G. & Terenzi, A. (2019). Int. J. Mol. Sci. 20, 3483. Web of Science CrossRef 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
Singh, M., Butcher, R. J. & Singh, N. K. (2008). Polyhedron, 27, 3151–3159. Web of Science CrossRef CAS Google Scholar
Sun, G.-X., Yang, M.-Y., Sun, Z.-H., Wu, H.-K., Liu, X.-H. & Wei, Y.-Y. (2014). Phosphorus Sulfur Silicon, 189, 1895–1900. Web of Science CrossRef CAS Google Scholar
Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). CrystalExplorer17. University of Western Australia. https://Hirshfeldsurface.net Google Scholar
Vaidya, A., Pathak, D. & Shah, K. (2020). Chem. Biol. Drug Des. 97, 572–591. Web of Science CrossRef PubMed Google Scholar
Wang, A., Xu, S., Chai, Y., Xia, G., Wang, B., Lv, K., Wang, D., Qin, X., Jiang, B., Wu, W., Liu, M. & Lu, Y. (2022). Bioorg. Med. Chem. 53, 116529. Web of Science CrossRef PubMed Google Scholar
Wang, Y.-T., Tang, G.-M. & Qiang, Z.-W. (2007). Polyhedron, 26, 4542–4550. Web of Science CrossRef CAS Google Scholar
Wang, Y. T., Wan, W. Z., Tang, G. M., Qiang, Z. W. & Li, T. D. J. (2010). J. Coord. Chem. 63, 206–213. Web of Science CrossRef CAS Google Scholar
Xiao, J., Ma, J.-P., Huang, R.-Q. & Dong, Y.-B. (2011). Acta Cryst. C67, m90–m92. Web of Science CrossRef IUCr Journals Google Scholar
Zachariah, S. M., Ramkumar, M., George, N. & Ashif, M. S. (2015). Res. J. Pharm. Biol. Chem. Sci, 6, 205–219. CAS Google Scholar
Zhang, H.-Z., Kasibhatla, S., Kuemmerle, J., Kemnitzer, W., Ollis-Mason, K., Qiu, L., Crogan-Grundy, C., Tseng, B., Drewe, J. & Cai, S. X. (2005). J. Med. Chem. 48, 5215–5223. Web of Science CrossRef PubMed CAS Google Scholar
Zhang, M.-Z., Mulholland, N., Beattie, D., Irwin, D., Gu, Y.-C., Chen, Q., Yang, G. F. & Clough, J. (2013). Eur. J. Med. Chem. 63, 22–32. Web of Science 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.