Crystal structure and Hirshfeld surface analysis of 3-amino-5-phenyl­thia­zolidin-2-iminium bromide

Duruskari, G.S.; Khalilov, A.N.; Akkurt, M.; Mammadova, G.Z.; Chyrka, T.; Maharramov, A.M.

doi:10.1107/S2056989019013069

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ISSN: 2056-9890

Volume 75| Part 10| October 2019| Pages 1544-1547

https://doi.org/10.1107/S2056989019013069

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Crystal structure and Hirshfeld surface analysis of 3-amino-5-phenylthiazolidin-2-iminium bromide

Gulnara Sh. Duruskari,^a Ali N. Khalilov,^a,^b Mehmet Akkurt,^c Gunay Z. Mammadova,^a Taras Chyrka ^d ^* and Abel M. Maharramov ^a

^aOrganic Chemistry Department, Baku State University, Z. Xalilov str. 23, Az, 1148 Baku, Azerbaijan, ^bDepartment of Physics and Chemistry, "Composite Materials" Scientific Research Center, Azerbaijan State Economic University (UNEC), H. Aliyev str. 135, Az 1063, Baku, Azerbaijan, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^dDepartment of Theoretical and Industrial Heat Engineering (TPT), National Technical University of Ukraine, "Igor Sikorsky Kyiv Polytechnic Institute", 03056, Kyiv, Ukraine
^*Correspondence e-mail: mustford@ukr.net

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 10 September 2019; accepted 22 September 2019; online 27 September 2019)

In the cation of the title salt, C₉H₁₂N₃S⁺·Br⁻, the thiazolidine ring adopts an envelope conformation with the C atom adjacent to the phenyl ring as the flap. In the crystal, N—H⋯Br hydrogen bonds link the components into a three-dimensional network. Weak π–π stacking interactions between the phenyl rings of adjacent cations also contribute to the molecular packing. A Hirshfeld surface analysis was conducted to quantify the contributions of the different intermolecular interactions and contacts.

Keywords: crystal structure; charge-assisted hydrogen bonding; thiazolidine ring; Hirshfeld surface analysis.

CCDC reference: 1955268

1. Chemical context

As well as their synthetic utility, thiazolidine derivatives possess a broad spectrum of biological activities such as antimalarial, antibacterial, antimicrobial, anti-inflammatory, anticancer, etc. The biological activities of compounds containing a thiazolidine core, such as 1,3-thiazolidines, 2,4-dione-, 4-oxo-thiazolidine, etc. were summarized in a recent review (Makwana & Malani, 2017 ). On the other hand, as hydrazones these N-containing ligands have been widely used in the synthesis of coordination compounds (Gurbanov et al., 2018a ,b ). The non-covalent donor or acceptor properties of N-containing ligands can also contribute to their catalytic activity, among other properties (Mahmudov et al., 2019 ; Zubkov et al., 2018 ). As part of our ongoing work in this area, we now describe the synthesis and structure of the title molecular salt, C₉H₁₂N₃S⁺·Br⁻, (I).

2. Structural commentary

In the cation of (I) (Fig. 1), the thiazolidine ring (S1/N1/C1–C3) adopts an envelope conformation with puckering parameters of Q(2) = 0.317 (2) Å and φ(2) = 225.2 (4)°: the flap atom is C1. In the arbitrarily chosen asymmetric unit, C1 has an R configuration, but symmetry generates a racemic mixture in the crystal. The dihedral angle between the mean plane of the thiazolidine ring (all atoms) and the phenyl ring (C4–C9) is 89.27 (13)°.

Figure 1
The molecular structure of the title salt. Displacement ellipsoids are drawn at the 50% probability level and the H⋯Br hydrogen bond is indicated by a dashed line.

3. Supramolecular features and Hirshfeld surface analysis

In the crystal, each cation forms N—H⋯Br hydrogen bonds (Table 1) as well as aromatic π–π stacking interactions between the phenyl rings of adjacent cations [Cg2⋯Cg2^iv = 3.7758 (16) Å; symmetry code: (iv) 1 − x, 1 − y, 2 − z; where Cg2 is the centroid of the phenyl ring of the cation]: chains of cations form along the [101] direction (Fig. 2). Taking into account the hydrogen bonding and π-π stacking, the overall connectivity is three-dimensional.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Br1ⁱ	0.90	2.68	3.530 (2)	158
N2—H2B⋯Br1ⁱⁱ	0.90	2.73	3.524 (2)	148
N3—H3A⋯Br1	0.90	2.38	3.271 (2)	169
N3—H3B⋯Br1ⁱⁱⁱ	0.90	2.56	3.337 (2)	145
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
Part of the crystal structure of the title compound, showing the formation of N—H⋯Br hydrogen bonds in the ac plane.

Hirshfeld surface analysis (Spackman & Jayatilaka, 2009 ; Spackman & McKinnon, 2002 ) was carried out with CrystalExplorer3.1 (Wolff et al., 2012 ) to further investigate the presence of hydrogen bonds and intermolecular interactions in the crystal structure (see supporting information). Fig. 3(a) shows the two-dimensional fingerprint of the sum of the contacts contributing to the Hirshfeld surface represented in normal mode while those delineated into H⋯H (41.5%), Br⋯N/N⋯Br (24.1%), C⋯H/H⋯C (13.8%) and S⋯H/H⋯S (11.7%) contacts, respectively, are shown in Fig. 3b–e. All contacts are listed in Table 2.

Table 2
Percentage contributions of interatomic contacts to the Hirshfeld surface for the title salt

Contact	Percentage contribution
H⋯H	41.5
Br⋯N/N⋯Br	24.1
C⋯H/H⋯C	13.8
S⋯H/H⋯S	11.7
N⋯H/H⋯N	3.6
C⋯C	3.3
N⋯C/C⋯N	1.5
N⋯N	0.3
S⋯C/C⋯S	0.3

Figure 3
The two-dimensional fingerprint plots of the title salt, showing (a) all interactions, and delineated into (b) H⋯H, (c) Br⋯N/N⋯Br, (d) C⋯H/H⋯C and (e) S⋯H/H⋯S interactions [d_e and d_i represent the distances from a point on the Hirshfeld surface to the nearest atoms outside (external) and inside (internal) the surface, respectively].

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.40, February 2019; Groom et al., 2016 ) for 2-thiazolidiniminium compounds gave eight hits, viz. BOBWIB (Khalilov et al., 2019 ), UDELUN (Akkurt et al., 2018 ), WILBIC (Marthi et al., 1994 ), WILBOI (Marthi et al., 1994), WILBOI01 (Marthi et al., 1994), YITCEJ (Martem'yanova et al., 1993a ), YITCAF (Martem'yanova et al., 1993b ) and YOPLUK (Marthi et al., 1995 ).

In the crystal of BOBWIB (Khalilov et al., 2019), the thiazolidine ring adopts an envelope conformation. In the crystal, centrosymmetrically related cations and anions are linked into dimeric units via N—H⋯Br hydrogen bonds, which are further connected by weak C—H⋯Br hydrogen bonds into chains parallel to [110]. In the crystal of UDELUN (Akkurt et al., 2018), C—H⋯Br and N—H⋯Br hydrogen bonds link the components into a three-dimensional network with the cations and anions stacked along the b-axis direction. Weak C—H⋯π interactions, which only involve the minor disorder component of the ring, also contribute to the molecular packing. In addition, there are also inversion-related Cl⋯Cl halogen bonds and C—Cl⋯π(ring) contacts. In the other structures, the 3-N atom carries a C substituent: the first three crystal structures were determined for racemic (WILBIC; Marthi et al., 1994) and two optically active samples (WILBOI and WILBOI01; Marthi et al., 1994) of 3-(2′-chloro-2′-phenylethyl)-2-thiazolidiniminium p-toluenesulfonate. In all three structures, the most disordered fragment of these molecules is the asymmetric C atom and the Cl atom attached to it. The disorder of the cation in the racemate corresponds to the presence of both enantiomers at each site in the ratio 0.821 (3): 0.179 (3). The system of hydrogen bonds connecting two cations and two anions into 12-membered rings is identical in the racemic and in the optically active crystals. YITCEJ (Martem'yanova et al., 1993a) is a product of the interaction of 2-amino-5-methylthiazoline with methyl iodide, with alkylation at the endocylic nitrogen atom, while YITCAF (Martem'yanova et al., 1993b) is a product of the reaction of 3-nitro-5-methoxy-, 3-nitro-5-chloro-, and 3-bromo-5-nitrosalicylaldehyde with the heterocyclic base to form the salt-like complexes.

5. Synthesis and crystallization

To a solution of 2.2 mmol (0.6 g) (1,2-dibromoethyl)benzene in 20 ml of ethanol were added 2.3 mmol (0.3 g) of thiosemicarbazide hydrochloride; 3-4 drops of piperidine were added and the mixture was refluxed for 7 h. The reaction mixture was cooled to room temperature and the solid product was precipitated from solution, collected by filtration and recrystallized from ethanol solution to give colourless crystals of (I) with a yield of 88%, m.p. = 468 K. Analysis calculated for C₉H₁₂BrN₃S: C 39.43; H 4.41; N 15.33. Found: C 39.40; H 4.39; N 15.30%. ¹H NMR (300 MHz, DMSO-d₆) : 4.16 (q, 1H, CH₂,³J_H–H = 5.4); 4.45 (t, 1H, CH₂, ³J_H–H = 8.4); 5.25 (t, 1H, CH-Ar, ³J_H–H = 5.4); 7.32–7.50 (m, 5H, 5Ar-H); 9.12 (s, 2H, NH₂); 9,78 (s, 1H, NH=). ¹³C NMR (75 MHz, DMSO-d₆): 44.42, 62.06, 127.59, 128.76, 129.17, 138.85, 168.53. MS (ESI), m/z: 194.28 [C₉H₁₂N₃S]⁺ and 79.88 Br⁻.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. All H atoms on C atoms were placed at calculated positions (C—H = 0.95–1.00 Å) and refined using a riding model. The N-bound hydrogen atoms were located from difference-Fourier maps and relocated to idealized locations (N—H = 0.90 Å) and refined as riding atoms. The constraint U_iso(H) = 1.2U_eq(carrier) was applied in all cases. One outlier ( $[\overline{1}]$ 01) was omitted in the final cycles of refinement.

Table 3
Experimental details

Crystal data
Chemical formula	C₉H₁₂N₃S⁺·Br⁻
M_r	274.19
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	10.5986 (5), 8.7168 (3), 13.0308 (5)
β (°)	111.513 (2)
V (Å³)	1119.99 (8)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	3.82
Crystal size (mm)	0.18 × 0.14 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2003 )
T_min, T_max	0.534, 0.661
No. of measured, independent and observed [I > 2σ(I)] reflections	8461, 2303, 1998
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.070, 1.02
No. of reflections	2303
No. of parameters	127
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.33
Computer programs: APEX2 and SAINT (Bruker, 2003), SHELXT2014 (Sheldrick, 2015a ), SHELXL2016 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2003 ).

Supporting information

CCDC reference: 1955268

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989019013069/hb7855sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019013069/hb7855Isup2.hkl

Hirshfeld surface analysis figures. DOI: https://doi.org/10.1107/S2056989019013069/hb7855sup3.docx

Supporting information file. DOI: https://doi.org/10.1107/S2056989019013069/hb7855Isup4.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2003).

3-Amino-5-phenylthiazolidin-2-iminium bromide top

Crystal data top

C₉H₁₂N₃S⁺·Br⁻	F(000) = 552
M_r = 274.19	D_x = 1.626 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.5986 (5) Å	Cell parameters from 3357 reflections
b = 8.7168 (3) Å	θ = 2.9–26.3°
c = 13.0308 (5) Å	µ = 3.82 mm⁻¹
β = 111.513 (2)°	T = 150 K
V = 1119.99 (8) Å³	Block, colorless
Z = 4	0.18 × 0.14 × 0.11 mm

Data collection top

Bruker APEXII CCD diffractometer	1998 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.029
Absorption correction: multi-scan (SADABS; Bruker, 2003)	θ_max = 26.4°, θ_min = 2.9°
T_min = 0.534, T_max = 0.661	h = −13→13
8461 measured reflections	k = −10→10
2303 independent reflections	l = −16→16

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)] = 0.027	Hydrogen site location: mixed
wR(F²) = 0.070	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0381P)² + 0.5896P] where P = (F_o² + 2F_c²)/3
2303 reflections	(Δ/σ)_max = 0.001
127 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.33 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	0.14662 (3)	0.38142 (3)	0.26547 (2)	0.02369 (10)
S1	0.31116 (7)	0.46985 (7)	0.58677 (5)	0.02034 (15)
N1	0.4802 (2)	0.6893 (2)	0.61070 (15)	0.0159 (4)
N2	0.5487 (2)	0.8083 (2)	0.57955 (15)	0.0183 (4)
H2A	0.635551	0.776693	0.607350	0.022*
H2B	0.535901	0.891753	0.615230	0.022*
N3	0.3577 (2)	0.6293 (2)	0.42850 (16)	0.0179 (4)
H3A	0.292719	0.572157	0.379225	0.021*
H3B	0.390509	0.709317	0.402415	0.021*
C1	0.4372 (3)	0.5007 (3)	0.72776 (19)	0.0214 (5)
H1A	0.513995	0.427032	0.741377	0.026*
C2	0.4890 (3)	0.6645 (3)	0.72463 (19)	0.0189 (5)
H2C	0.432008	0.739798	0.744749	0.023*
H2D	0.583832	0.675080	0.776759	0.023*
C3	0.3879 (2)	0.6085 (3)	0.53385 (19)	0.0154 (5)
C4	0.3746 (2)	0.4760 (3)	0.81375 (18)	0.0168 (5)
C5	0.4280 (3)	0.3584 (3)	0.8912 (2)	0.0212 (5)
H5A	0.497585	0.293462	0.886358	0.025*
C6	0.3773 (3)	0.3379 (3)	0.97571 (19)	0.0208 (5)
H6A	0.412191	0.258553	1.028582	0.025*
C7	0.2769 (3)	0.4330 (3)	0.9816 (2)	0.0225 (5)
H7A	0.244208	0.420521	1.039905	0.027*
C8	0.2230 (3)	0.5463 (3)	0.9041 (2)	0.0265 (6)
H8A	0.152610	0.610477	0.908407	0.032*
C9	0.2715 (3)	0.5662 (3)	0.8203 (2)	0.0249 (6)
H9A	0.233208	0.643424	0.766388	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02460 (15)	0.02084 (15)	0.02181 (15)	−0.00181 (11)	0.00401 (11)	−0.00181 (10)
S1	0.0263 (3)	0.0175 (3)	0.0173 (3)	−0.0062 (3)	0.0081 (2)	−0.0012 (2)
N1	0.0197 (10)	0.0165 (10)	0.0132 (9)	−0.0036 (8)	0.0078 (8)	−0.0004 (8)
N2	0.0208 (11)	0.0162 (10)	0.0198 (10)	−0.0030 (9)	0.0099 (9)	−0.0004 (8)
N3	0.0239 (11)	0.0151 (10)	0.0144 (10)	−0.0011 (9)	0.0066 (8)	−0.0014 (8)
C1	0.0215 (13)	0.0233 (13)	0.0184 (12)	0.0033 (11)	0.0061 (10)	0.0023 (10)
C2	0.0225 (13)	0.0215 (12)	0.0126 (11)	−0.0041 (10)	0.0064 (10)	−0.0018 (10)
C3	0.0176 (12)	0.0121 (11)	0.0178 (12)	0.0027 (9)	0.0082 (10)	−0.0009 (9)
C4	0.0171 (12)	0.0193 (12)	0.0131 (11)	−0.0054 (10)	0.0046 (9)	−0.0010 (9)
C5	0.0175 (12)	0.0183 (12)	0.0255 (13)	−0.0020 (10)	0.0051 (10)	−0.0066 (10)
C6	0.0244 (13)	0.0193 (12)	0.0147 (12)	−0.0050 (10)	0.0027 (10)	0.0016 (10)
C7	0.0215 (13)	0.0253 (13)	0.0214 (13)	−0.0100 (11)	0.0085 (11)	−0.0029 (11)
C8	0.0208 (13)	0.0258 (14)	0.0335 (15)	−0.0012 (11)	0.0108 (12)	−0.0007 (12)
C9	0.0219 (13)	0.0246 (13)	0.0266 (14)	0.0041 (11)	0.0070 (11)	0.0036 (11)

Geometric parameters (Å, º) top

S1—C3	1.735 (2)	C2—H2C	0.9900
S1—C1	1.853 (2)	C2—H2D	0.9900
N1—C3	1.318 (3)	C4—C9	1.374 (4)
N1—N2	1.408 (3)	C4—C5	1.404 (3)
N1—C2	1.469 (3)	C5—C6	1.403 (4)
N2—H2A	0.9000	C5—H5A	0.9500
N2—H2B	0.9000	C6—C7	1.373 (4)
N3—C3	1.303 (3)	C6—H6A	0.9500
N3—H3A	0.9000	C7—C8	1.378 (4)
N3—H3B	0.9000	C7—H7A	0.9500
C1—C4	1.513 (3)	C8—C9	1.378 (4)
C1—C2	1.535 (4)	C8—H8A	0.9500
C1—H1A	1.0000	C9—H9A	0.9500

C3—S1—C1	91.16 (11)	N3—C3—N1	123.6 (2)
C3—N1—N2	119.48 (18)	N3—C3—S1	123.08 (18)
C3—N1—C2	116.3 (2)	N1—C3—S1	113.33 (17)
N2—N1—C2	123.48 (18)	C9—C4—C5	119.6 (2)
N1—N2—H2A	102.6	C9—C4—C1	122.7 (2)
N1—N2—H2B	104.8	C5—C4—C1	117.7 (2)
H2A—N2—H2B	111.4	C6—C5—C4	119.2 (2)
C3—N3—H3A	120.2	C6—C5—H5A	120.4
C3—N3—H3B	121.7	C4—C5—H5A	120.4
H3A—N3—H3B	117.4	C7—C6—C5	119.6 (2)
C4—C1—C2	114.2 (2)	C7—C6—H6A	120.2
C4—C1—S1	111.16 (17)	C5—C6—H6A	120.2
C2—C1—S1	104.09 (16)	C6—C7—C8	120.9 (2)
C4—C1—H1A	109.1	C6—C7—H7A	119.5
C2—C1—H1A	109.1	C8—C7—H7A	119.5
S1—C1—H1A	109.1	C9—C8—C7	119.7 (3)
N1—C2—C1	105.85 (19)	C9—C8—H8A	120.1
N1—C2—H2C	110.6	C7—C8—H8A	120.1
C1—C2—H2C	110.6	C4—C9—C8	120.9 (2)
N1—C2—H2D	110.6	C4—C9—H9A	119.5
C1—C2—H2D	110.6	C8—C9—H9A	119.5
H2C—C2—H2D	108.7

C3—S1—C1—C4	147.17 (19)	C2—C1—C4—C9	53.9 (3)
C3—S1—C1—C2	23.78 (17)	S1—C1—C4—C9	−63.5 (3)
C3—N1—C2—C1	26.7 (3)	C2—C1—C4—C5	−124.2 (2)
N2—N1—C2—C1	−163.3 (2)	S1—C1—C4—C5	118.4 (2)
C4—C1—C2—N1	−152.1 (2)	C9—C4—C5—C6	−1.7 (4)
S1—C1—C2—N1	−30.7 (2)	C1—C4—C5—C6	176.5 (2)
N2—N1—C3—N3	1.9 (3)	C4—C5—C6—C7	−0.2 (4)
C2—N1—C3—N3	172.3 (2)	C5—C6—C7—C8	1.5 (4)
N2—N1—C3—S1	−178.62 (16)	C6—C7—C8—C9	−0.9 (4)
C2—N1—C3—S1	−8.2 (3)	C5—C4—C9—C8	2.2 (4)
C1—S1—C3—N3	169.2 (2)	C1—C4—C9—C8	−175.8 (2)
C1—S1—C3—N1	−10.29 (19)	C7—C8—C9—C4	−1.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Br1ⁱ	0.90	2.68	3.530 (2)	158
N2—H2B···Br1ⁱⁱ	0.90	2.73	3.524 (2)	148
N3—H3A···Br1	0.90	2.38	3.271 (2)	169
N3—H3B···Br1ⁱⁱⁱ	0.90	2.56	3.337 (2)	145

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

Percentage contributions of interatomic contacts to the Hirshfeld surface for the title salt top

Contact	Percentage contribution
H···H	41.5
Br···N/N···Br	24.1
C···H/H···C	13.8
S···H/H···S	11.7
N···H/H···N	3.6
C···C	3.3
N···C/C···N	1.5
N···N	0.3
S···C/C···S	0.3

Acknowledgements

ANK is grateful to Baku State University for the "50 + 50" individual grant in support of this work.

Funding information

ANK is grateful to Baku State University for the "50 + 50" individual grant insupport of this work.

References

Akkurt, M., Duruskari, G. S., Toze, F. A. A., Khalilov, A. N. & Huseynova, A. T. (2018). Acta Cryst. E74, 1168–1172. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2003). APEX2, SAINT and SADABS. 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., Huseynov, F. E., Mahmoudi, G., Maharramov, A. M., Guedes da Silva, F. C., Mahmudov, K. T. & Pombeiro, A. J. L. (2018a). Inorg. Chim. Acta, 469, 197–201. Web of Science CSD CrossRef CAS Google Scholar
Gurbanov, A. V., Maharramov, A. M., Zubkov, F. I., Saifutdinov, A. M. & Guseinov, F. I. (2018b). Aust. J. Chem. 71, 190–194. Web of Science CrossRef CAS Google Scholar
Khalilov, A. N., Atioğlu, Z., Akkurt, M., Duruskari, G. S., Toze, F. A. A. & Huseynova, A. T. (2019). Acta Cryst. E75, 662–666. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mahmudov, K. T., Gurbanov, A. V., Guseinov, F. I. & Guedes da Silva, M. F. C. (2019). Coord. Chem. Rev. 387, 32–46. Web of Science CrossRef CAS Google Scholar
Makwana, H. R. & Malani, A. H. (2017). IOSR J. Appl. Chem. 10, 76–84. CAS Google Scholar
Martem'yanova, N. A., Chunaev, Y. M., Przhiyalgovskaya, N. M., Kurkovskaya, L. N., Filipenko, O. S. & Aldoshin, S. M. (1993a). Khim. Geterotsikl. Soedin. pp. 415–419. Google Scholar
Martem'yanova, N. A., Chunaev, Y. M., Przhiyalgovskaya, N. M., Kurkovskaya, L. N., Filipenko, O. S. & Aldoshin, S. M. (1993b). Khim. Geterotsikl. Soedin. pp. 420–425. Google Scholar
Marthi, K., Larsen, M., Ács, M., Bálint, J. & Fogassy, E. (1995). Acta Chem. Scand. 49, 20–27. CSD CrossRef CAS Web of Science Google Scholar
Marthi, K., Larsen, S., Ács, M., Bálint, J. & Fogassy, E. (1994). Acta Cryst. B50, 762–771. CSD CrossRef CAS Web of Science 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. & McKinnon, J. J. (2002). CrystEngComm, 4, 378–392. Web of Science CrossRef CAS Google Scholar
Spackman, M. & Jayatilaka, D. (2009). CrystEngComm, 11, 19–32. Web of Science CrossRef CAS Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wolff, S. K., Grimwood, D. J., McKinnon, J. J., Turner, M. J., Jayatilaka, D. & Spackman, M. A. (2012). Crystal Explorer. University of Western Australia. Google Scholar
Zubkov, F. I., Mertsalov, D. F., Zaytsev, V. P., Varlamov, A. V., Gurbanov, A. V., Dorovatovskii, P. V., Timofeeva, T. V., Khrustalev, V. N. & Mahmudov, K. T. (2018). J. Mol. Liq. 249, 949–952. Web of Science CSD CrossRef CAS Google Scholar

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