Crystal structure and Hirshfeld surface analysis of 2,2′-[(3,5-di-tert-butyl-4-hy­droxy­phen­yl)methanedi­yl]bis­(3-hy­droxy-5,5-di­methyl­cyclo­hex-2-en-1-one)

Khalilov, A.N.; Khrustalev, V.N.; Aleksandrova, L.V.; Akkurt, M.; Rzayev, R.M.; Bhattarai, A.; Mamedov, İ.G.

doi:10.1107/S2056989023003171

research communications

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ISSN: 2056-9890

Volume 79| Part 5| May 2023| Pages 436-440

https://doi.org/10.1107/S2056989023003171

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Crystal structure and Hirshfeld surface analysis of 2,2′-[(3,5-di-tert-butyl-4-hydroxyphenyl)methanediyl]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one)

Ali N. Khalilov,^a,^b Victor N. Khrustalev,^c,^d Larissa V. Aleksandrova,^c Mehmet Akkurt,^e Rovnag M. Rzayev,^a Ajaya Bhattarai ^f ^* and İbrahim G. Mamedov ^b

^a"Composite Materials" Scientific Research Center, Azerbaijan State Economic University (UNEC), H. Aliyev str. 135, Az 1063, Baku, Azerbaijan, ^bDepartment of Chemistry, Baku State University, Z. Khalilov str. 23, Az, 1148, Baku, Azerbaijan, ^cPeoples' Friendship University of Russia (RUDN University), Miklukho-Maklay St.6, Moscow, 117198, Russian Federation, ^dN. D. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, Moscow, 119991, Russian Federation, ^eDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye, and ^fDepartment of Chemistry, M.M.A.M.C (Tribhuvan University) Biratnagar, Nepal
^*Correspondence e-mail: ajaya.bhattarai@mmamc.tu.edu.np

Edited by A. Briceno, Venezuelan Institute of Scientific Research, Venezuela (Received 10 March 2023; accepted 5 April 2023; online 14 April 2023)

In the title compound, C₃₁H₄₄O₅, molecules are connected by O—H⋯O and C—H⋯O hydrogen bonds, forming hydrogen-bonded zigzag chains running along the b axis and parallel to the (001) plane. The molecular packing is stabilized by van der Waals interactions between these chains along the a and c axes. The intermolecular interactions in the crystal structure were quantified and analysed using Hirshfeld surface analysis.

Keywords: crystal structure; hydrogen bonds; hydrogen-bonded zigzag chains; van der Waals interactions; 1,8-dioxo-octahydroxanthene; Hirshfeld surface analysis.

CCDC reference: 2254247

1. Chemical context

The various carbon–carbon bond-formation techniques play important roles in organic chemistry (Celik et al., 2023 ; Chalkha et al., 2023 ; Tapera et al., 2022 ). Xanthene derivatives have broad applications in medicine as a result of their anti-inflammatory, antibacterial, antiviral, antifungal, anti-depressant, antiplasmodial and anti-malarial activity (Maia et al., 2021 ). They are a special class of oxygen-incorporating tricyclic systems. The xanthene moiety is also found in various natural compounds and has a wide spectrum of therapeutic and pharmacological properties. Aside from medicinal applications, xanthene dyes have been used for diagnostic and imaging applications (Khan & Sekar, 2022 ; Majumdar et al., 2022 ; Lakhrissi et al., 2022 ).

Thus, in the framework of our ongoing structural studies (Zubkov et al., 2018 ; Gurbanov et al., 2020 ; Maharramov et al., 2021 , 2022 ), we report the crystal structure and Hirshfeld surface analysis of the title compound, 2,2′-[(3,5-di-tert-butyl-4-hydroxyphenyl)methanediyl]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one).

2. Structural commentary

As seen in Fig. 1, each of the cyclohexenone rings (C2–C7 and C10–C15) of the title compound adopts an envelope conformation. The puckering parameters (Cremer & Pople, 1975 ) are Q_T = 0.5027 (12) Å, θ = 63.26 (14)°, φ = 179.78 (16)° for the C2–C7 ring, and Q_T = 0.4920 (11) Å, θ = 67.89 (13)°, φ = 167.63 (14)° for the C10–C15 ring. The mean planes [maximum deviations are 0.353 (1) Å for C5 and 0.332 (1) Å for C13] of the cyclohexane rings C2–C7 and C10–C15 subtend a dihedral angle of 39.59 (5)°, and they form dihedral angles of 56.25 (5) and 50.23 (5)°, respectively, with the benzene ring (C18–C23) of the 3,5-di-tert-butyl-4-hydroxyphenyl moiety. The bond lengths and angles in the title compound are within normal ranges. The orientation of the hydroxy and carbonyl O atoms permits the formation of two intramolecular O—H⋯O hydrogen bonds as they face one another (Fig. 1, Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O4	0.930 (19)	1.711 (19)	2.6201 (11)	164.7 (17)
O3—H3O⋯O2	0.950 (19)	1.68 (2)	2.6174 (11)	170.3 (17)
O5—H5O⋯O4ⁱ	0.848 (19)	2.128 (18)	2.8285 (11)	139.7 (16)
C14—H14A⋯O5ⁱⁱ	0.99	2.48	3.1912 (12)	128
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 1
The molecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at the 30% probability level.

3. Supramolecular features and Hirshfeld surface analysis

In the crystal, O—H⋯O and C—H⋯O hydrogen bonds (Table 1) link the molecules, forming zigzag chains running along the [010] direction and parallel to the (001) plane (Figs. 2 and 3). The molecular packing is stabilized by van der Waals interactions between these chains along the a and c axes.

Figure 2
The packing of the title compound viewed along the a-axis with O—H⋯O and C—H⋯O hydrogen bonds shown as dashed lines.

Figure 3
A view of the zigzag chains running along the b-axis direction of the title compound with O—H⋯O and C—H⋯O hydrogen bonds shown as dashed lines.

To quantify the intermolecular interactions, a Hirshfeld surface analysis was performed and CrystalExplorer17 (Turner et al., 2017 ) was used to obtain the accompanying two-dimensional fingerprint plots. Fig. 4 shows the Hirshfeld surface mapped onto d_norm using a common surface resolution and a constant color scale of −0.4467 (red) to 1.6498 (blue) a.u. On the Hirshfeld surface, shorter and longer contacts are indicated by red and blue spots, respectively, and contacts with lengths about equal to the sum of the van der Waals radii are indicated by white spots. The O—H⋯O and C—H⋯O interactions are represented by the two most significant red spots on the d_norm surface (Tables 1 and 2).

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

H4B⋯H16B	2.39	x, $[{3\over 2}]$ − y, $[{1\over 2}]$ + z
H4A⋯H1	2.31	1 − x, $[{1\over 2}]$ + y, $[{3\over 2}]$ − z
H17B⋯O2	2.65	1 − x, 1 − y, 1 − z
O4⋯H5O	2.12	2 − x, $[{1\over 2}]$ + y, $[{3\over 2}]$ − z
C17⋯H30B	3.10	x, $[{1\over 2}]$ − y, − $[{1\over 2}]$ + z
H26C⋯H6A	2.58	1 + x, y, z
H25B⋯H17A	2.57	2 − x, 1 − y, 1 − z

Figure 4
(a) Front and (b) back sides of the three-dimensional Hirshfeld surface of the title compound mapped over d_norm, with a fixed colour scale of −0.4467 to 1.6498 a.u.

Fig. 5 depicts the two-dimensional fingerprint plots of (d_i, d_e) points from all the contacts contributing to the Hirshfeld surface analysis in normal mode for all atoms. The most important intermolecular interactions are H⋯H contacts, contributing 76.8% to the overall crystal packing. Other interactions and their respective contributions are O⋯H/H⋯O (15.2%), C⋯H/H⋯C (6.9%) and O⋯O (1.0%). The Hirshfeld surface study verifies the significance of H-atom interactions in the packing formation. The significant frequency of H⋯H and O⋯H/H⋯O interactions implies that van der Waals interactions and hydrogen bonding are important in crystal packing (Hathwar et al., 2015 ).

Figure 5
The two-dimensional fingerprint plots of the title compound, showing (a) all interactions, and delineated into (b) H⋯H, (c) O⋯H/H⋯O and (d) C⋯H/H⋯C 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

The ten most similar compounds found in a search of the Cambridge Structural Database (CSD, Version 5.42, update of September 2021; Groom et al., 2016 ) for the 2,2′-(ethane-1,1-diyl)bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one) moiety are 2,2′-[(4-ethoxyphenyl)methylene]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1- one) (I; Sureshbabu & Sughanya, 2012 ), 2,2′-[(3-bromo-4-hydroxy-5-methoxyphenyl)methylidene]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one) (II; Sughanya & Sureshbabu, 2012 ), 2,2′-[(1E)-3-phenylprop-2-ene-1,1-diyl]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one) (III; Zhu et al., 2011 ), (E)-2,2′-[3-(4-chlorophenyl)prop-2-ene-1,1-diyl]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one) (IV; Cha et al., 2013a ), (E)-2,2′-[3-(4-fluorophenyl)prop-2-ene-1,1-diyl]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one) (V; Cha et al., 2013b ), (E)-2,2′-[3-(2-nitrophenyl)prop-2-ene-1,1-diyl]bis(3-hydroxy-5,5-dimethylcyclohex- 2-en-1-one) (VI; Cha et al., 2011 ), 2,2′-[(E)-3-(4-nitrophenyl)prop-2-ene-1,1-diyl]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one) (VII; Cha et al., 2012 ), bis(2- hydroxy-4,4-dimethyl-6-oxo-1-cyclohexenyl)phenylmethane (VIII; Bolte et al., 1997a ), 2,2′-[(2-nitrophenyl)methylene]bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) (IX; Steiger et al., 2020 ) and 2,2′-[(3-hydroxyphenyl)methylene]bis(3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one) (X; Bolte et al., 2001b ).

In I, II, III, IV, VIII, IX and X, the two cyclohexane rings adopt an envelope conformation, while in VI and VII they exhibit a half-chair conformation. In all of these crystals, molecules are connected via O—H⋯O hydrogen bonds. In X, there are also O—H⋯O hydrogen bonds involving the water molecules. In III, IV, V, VI, VII and IX, C—H⋯O hydrogen bonds also contribute to the cohesion of the crystal structure.

5. Synthesis and crystallization

To a solution of 3,5-di-tert-butyl-4-hydroxybenzaldehyde (1 g, 4.3 mmol) and 5,5-dimethylcyclohexane-1,3-dione (1.2 g, 8.6 mmol) in ethanol (15 mL), piperidine (2–3 drops) was added and the mixture was refluxed for 3 h. Then 10 mL of ethanol was removed from the reaction mixture, which was left overnight. The precipitated crystals were separated by filtration and recrystallized from an ethanol/water (4:1) solution (yield 65%; m.p. 465–466 K).

¹H NMR (300 MHz, CDCl₃, ppm): 1.05 (s, 6H, 2CH₃), 1.08 (s, 6H, 2CH₃), 1.41 (s, 18H, 6CH₃), 2.05–2.35 (m, 8H, 4CH₂), 5.39 (s, 1H, CH), 5.69 (s, 1H, OH), 6.65 (s, 2H, arom.), 11.21 (s, 2H, 2OH); ¹³C NMR (75 MHz, CDCl₃, ppm): 26.4, 28.7, 30.8, 31.7, 32.6, 36.5, 45.3, 51.8, 111.6, 122.9, 13.8, 136.8, 153.2, 176.4, 202.3.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. All C-bound H atoms were placed at calculated positions and refined using a riding model, with C—H = 0.95–1.00 Å, and with U_iso(H) = 1.2 or 1.5U_eq(C). The O-bound H atoms were located in a difference-Fourier map and were freely refined.

Table 3
Experimental details

Crystal data
Chemical formula	C₃₁H₄₄O₅
M_r	496.66
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	12.40591 (9), 10.98934 (10), 20.58063 (17)
β (°)	98.4293 (7)
V (Å³)	2775.50 (4)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.63
Crystal size (mm)	0.33 × 0.21 × 0.18

Data collection
Diffractometer	XtaLAB Synergy, Dualflex, HyPix
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2022 $[Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.362, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	61789, 5870, 5540
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.104, 1.03
No. of reflections	5870
No. of parameters	347
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.26
Computer programs: CrysAlis PRO (Rigaku OD, 2022 $[Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT2014/5 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2254247

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989023003171/zn2027sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023003171/zn2027Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989023003171/zn2027Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO 1.171.42.72a (Rigaku OD, 2022); cell refinement: CrysAlis PRO 1.171.42.72a (Rigaku OD, 2022); data reduction: CrysAlis PRO 1.171.42.72a (Rigaku OD, 2022); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

2,2'-[(3,5-Di-tert-butyl-4-hydroxyphenyl)methanediyl]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one) top

Crystal data top

C₃₁H₄₄O₅	F(000) = 1080
M_r = 496.66	D_x = 1.189 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 12.40591 (9) Å	Cell parameters from 41183 reflections
b = 10.98934 (10) Å	θ = 3.6–77.8°
c = 20.58063 (17) Å	µ = 0.63 mm⁻¹
β = 98.4293 (7)°	T = 100 K
V = 2775.50 (4) Å³	Prism, colourless
Z = 4	0.33 × 0.21 × 0.18 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	5540 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube	R_int = 0.047
φ and ω scans	θ_max = 77.9°, θ_min = 3.6°
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2022)	h = −13→15
T_min = 0.362, T_max = 1.000	k = −13→13
61789 measured reflections	l = −26→26
5870 independent reflections

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: mixed
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0581P)² + 0.9674P] where P = (F_o² + 2F_c²)/3
5870 reflections	(Δ/σ)_max = 0.001
347 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.26 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
O1	0.67352 (6)	0.68092 (7)	0.79581 (4)	0.02223 (17)
H1O	0.7151 (15)	0.6706 (16)	0.7621 (9)	0.046 (5)*
O2	0.39003 (6)	0.48506 (8)	0.65828 (4)	0.02641 (18)
O3	0.47791 (6)	0.57142 (7)	0.55974 (4)	0.02175 (17)
H3O	0.4532 (15)	0.5356 (17)	0.5969 (9)	0.049 (5)*
O4	0.79022 (6)	0.69306 (7)	0.69970 (3)	0.01951 (16)
O5	0.99582 (6)	0.26695 (8)	0.81386 (4)	0.02279 (17)
H5O	1.0464 (15)	0.2572 (16)	0.7907 (9)	0.041 (4)*
C1	0.61903 (8)	0.51072 (9)	0.68241 (5)	0.0160 (2)
H1	0.5758	0.4455	0.6566	0.019*
C2	0.54278 (8)	0.56043 (9)	0.72776 (5)	0.0171 (2)
C3	0.57463 (8)	0.63356 (9)	0.78073 (5)	0.0186 (2)
C4	0.50033 (9)	0.66692 (11)	0.82932 (6)	0.0245 (2)
H4A	0.4701	0.7491	0.8186	0.029*
H4B	0.5435	0.6707	0.8737	0.029*
C5	0.40583 (9)	0.57748 (10)	0.83053 (5)	0.0217 (2)
C6	0.35058 (9)	0.56319 (12)	0.75965 (6)	0.0265 (2)
H6A	0.2947	0.4985	0.7579	0.032*
H6B	0.3127	0.6401	0.7454	0.032*
C7	0.42799 (9)	0.53188 (10)	0.71194 (5)	0.0211 (2)
C8	0.32572 (10)	0.62886 (12)	0.87359 (6)	0.0307 (3)
H8A	0.3632	0.6401	0.9185	0.046*
H8B	0.2650	0.5719	0.8739	0.046*
H8C	0.2977	0.7073	0.8559	0.046*
C9	0.44652 (10)	0.45389 (12)	0.85835 (6)	0.0304 (3)
H9A	0.4965	0.4189	0.8307	0.046*
H9B	0.3844	0.3991	0.8590	0.046*
H9C	0.4848	0.4646	0.9031	0.046*
C10	0.64598 (8)	0.60075 (9)	0.63062 (5)	0.0162 (2)
C11	0.57732 (8)	0.61877 (9)	0.57293 (5)	0.0176 (2)
C12	0.60567 (8)	0.69745 (10)	0.51805 (5)	0.0197 (2)
H12A	0.5757	0.7800	0.5224	0.024*
H12B	0.5709	0.6634	0.4756	0.024*
C13	0.72887 (8)	0.70697 (10)	0.51767 (5)	0.0192 (2)
C14	0.78192 (8)	0.74319 (10)	0.58701 (5)	0.0193 (2)
H14A	0.8614	0.7292	0.5905	0.023*
H14B	0.7707	0.8315	0.5926	0.023*
C15	0.74074 (8)	0.67709 (9)	0.64281 (5)	0.0169 (2)
C16	0.75463 (10)	0.80530 (11)	0.46958 (6)	0.0266 (2)
H16A	0.7221	0.8826	0.4804	0.040*
H16B	0.7244	0.7814	0.4247	0.040*
H16C	0.8338	0.8148	0.4728	0.040*
C17	0.77368 (9)	0.58492 (10)	0.49695 (5)	0.0231 (2)
H17A	0.8532	0.5899	0.5002	0.035*
H17B	0.7422	0.5667	0.4515	0.035*
H17C	0.7543	0.5202	0.5259	0.035*
C18	0.72031 (8)	0.44419 (9)	0.71819 (5)	0.0169 (2)
C19	0.80443 (8)	0.41235 (9)	0.68346 (5)	0.0176 (2)
H19	0.7982	0.4341	0.6384	0.021*
C20	0.89755 (8)	0.34983 (9)	0.71204 (5)	0.0174 (2)
C21	0.90520 (8)	0.32072 (9)	0.77939 (5)	0.0177 (2)
C22	0.82019 (8)	0.34622 (9)	0.81580 (5)	0.0175 (2)
C23	0.72883 (8)	0.40755 (9)	0.78330 (5)	0.0177 (2)
H23	0.6702	0.4248	0.8068	0.021*
C24	0.98864 (9)	0.31798 (10)	0.67141 (5)	0.0206 (2)
C25	0.95624 (10)	0.35071 (13)	0.59845 (5)	0.0307 (3)
H25A	0.8885	0.3087	0.5811	0.046*
H25B	1.0142	0.3255	0.5738	0.046*
H25C	0.9454	0.4388	0.5941	0.046*
C26	1.09148 (9)	0.39337 (11)	0.69613 (6)	0.0249 (2)
H26A	1.0742	0.4803	0.6916	0.037*
H26B	1.1491	0.3734	0.6700	0.037*
H26C	1.1164	0.3743	0.7424	0.037*
C27	1.01253 (9)	0.17986 (11)	0.67306 (6)	0.0249 (2)
H27A	1.0304	0.1529	0.7188	0.037*
H27B	1.0742	0.1632	0.6496	0.037*
H27C	0.9481	0.1359	0.6519	0.037*
C28	0.82892 (9)	0.31386 (10)	0.88945 (5)	0.0190 (2)
C29	0.72191 (9)	0.33977 (11)	0.91629 (5)	0.0248 (2)
H29A	0.7048	0.4267	0.9118	0.037*
H29B	0.7299	0.3167	0.9628	0.037*
H29C	0.6628	0.2924	0.8914	0.037*
C30	0.85384 (9)	0.17769 (10)	0.90225 (5)	0.0221 (2)
H30A	0.7966	0.1284	0.8769	0.033*
H30B	0.8564	0.1604	0.9492	0.033*
H30C	0.9244	0.1578	0.8888	0.033*
C31	0.91838 (9)	0.39252 (10)	0.92908 (5)	0.0235 (2)
H31A	0.9879	0.3783	0.9130	0.035*
H31B	0.9254	0.3705	0.9757	0.035*
H31C	0.8987	0.4787	0.9237	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0206 (4)	0.0269 (4)	0.0198 (4)	−0.0059 (3)	0.0049 (3)	−0.0048 (3)
O2	0.0183 (4)	0.0367 (5)	0.0231 (4)	−0.0052 (3)	−0.0008 (3)	−0.0003 (3)
O3	0.0160 (4)	0.0296 (4)	0.0183 (4)	−0.0029 (3)	−0.0017 (3)	−0.0008 (3)
O4	0.0183 (4)	0.0242 (4)	0.0154 (3)	−0.0040 (3)	0.0005 (3)	−0.0014 (3)
O5	0.0179 (4)	0.0335 (4)	0.0168 (3)	0.0085 (3)	0.0021 (3)	0.0044 (3)
C1	0.0152 (5)	0.0165 (5)	0.0156 (4)	−0.0006 (4)	0.0002 (3)	−0.0001 (4)
C2	0.0156 (5)	0.0178 (5)	0.0178 (5)	0.0016 (4)	0.0017 (4)	0.0031 (4)
C3	0.0178 (5)	0.0184 (5)	0.0196 (5)	0.0007 (4)	0.0030 (4)	0.0029 (4)
C4	0.0252 (6)	0.0245 (5)	0.0254 (5)	−0.0009 (4)	0.0093 (4)	−0.0035 (4)
C5	0.0180 (5)	0.0250 (5)	0.0231 (5)	0.0034 (4)	0.0061 (4)	0.0048 (4)
C6	0.0157 (5)	0.0384 (7)	0.0255 (6)	0.0018 (4)	0.0034 (4)	0.0043 (5)
C7	0.0175 (5)	0.0236 (5)	0.0215 (5)	0.0004 (4)	0.0008 (4)	0.0044 (4)
C8	0.0269 (6)	0.0366 (7)	0.0312 (6)	0.0074 (5)	0.0129 (5)	0.0055 (5)
C9	0.0268 (6)	0.0315 (6)	0.0352 (6)	0.0062 (5)	0.0124 (5)	0.0131 (5)
C10	0.0162 (5)	0.0165 (5)	0.0157 (4)	0.0008 (4)	0.0015 (4)	−0.0007 (3)
C11	0.0169 (5)	0.0182 (5)	0.0173 (5)	0.0016 (4)	0.0009 (4)	−0.0022 (4)
C12	0.0198 (5)	0.0221 (5)	0.0161 (5)	0.0021 (4)	−0.0007 (4)	0.0009 (4)
C13	0.0203 (5)	0.0225 (5)	0.0145 (5)	0.0002 (4)	0.0015 (4)	0.0016 (4)
C14	0.0191 (5)	0.0210 (5)	0.0177 (5)	−0.0030 (4)	0.0022 (4)	0.0002 (4)
C15	0.0165 (5)	0.0180 (5)	0.0159 (4)	0.0018 (4)	0.0016 (4)	−0.0009 (4)
C16	0.0274 (6)	0.0315 (6)	0.0210 (5)	−0.0006 (5)	0.0033 (4)	0.0075 (4)
C17	0.0234 (5)	0.0273 (6)	0.0185 (5)	0.0028 (4)	0.0033 (4)	−0.0015 (4)
C18	0.0160 (5)	0.0163 (5)	0.0177 (5)	0.0002 (4)	0.0005 (4)	0.0001 (4)
C19	0.0189 (5)	0.0190 (5)	0.0147 (4)	0.0002 (4)	0.0015 (4)	0.0004 (4)
C20	0.0165 (5)	0.0188 (5)	0.0166 (5)	0.0005 (4)	0.0017 (4)	−0.0007 (4)
C21	0.0167 (5)	0.0184 (5)	0.0170 (5)	0.0018 (4)	−0.0003 (4)	0.0011 (4)
C22	0.0193 (5)	0.0175 (5)	0.0155 (5)	0.0004 (4)	0.0017 (4)	0.0007 (4)
C23	0.0168 (5)	0.0183 (5)	0.0182 (5)	0.0012 (4)	0.0036 (4)	0.0004 (4)
C24	0.0178 (5)	0.0278 (6)	0.0164 (5)	0.0046 (4)	0.0032 (4)	0.0019 (4)
C25	0.0249 (6)	0.0499 (8)	0.0182 (5)	0.0127 (5)	0.0067 (4)	0.0051 (5)
C26	0.0192 (5)	0.0281 (6)	0.0279 (5)	0.0018 (4)	0.0048 (4)	0.0071 (4)
C27	0.0223 (5)	0.0286 (6)	0.0235 (5)	0.0050 (4)	0.0024 (4)	−0.0053 (4)
C28	0.0211 (5)	0.0209 (5)	0.0151 (5)	0.0025 (4)	0.0029 (4)	0.0012 (4)
C29	0.0258 (6)	0.0315 (6)	0.0184 (5)	0.0060 (4)	0.0072 (4)	0.0039 (4)
C30	0.0265 (5)	0.0211 (5)	0.0186 (5)	0.0018 (4)	0.0028 (4)	0.0031 (4)
C31	0.0272 (6)	0.0237 (5)	0.0189 (5)	0.0006 (4)	0.0011 (4)	−0.0018 (4)

Geometric parameters (Å, º) top

O1—C3	1.3268 (13)	C14—H14B	0.9900
O1—H1O	0.930 (19)	C16—H16A	0.9800
O2—C7	1.2466 (14)	C16—H16B	0.9800
O3—C11	1.3293 (13)	C16—H16C	0.9800
O3—H3O	0.950 (19)	C17—H17A	0.9800
O4—C15	1.2521 (12)	C17—H17B	0.9800
O5—C21	1.3720 (12)	C17—H17C	0.9800
O5—H5O	0.848 (19)	C18—C23	1.3882 (14)
C1—C2	1.5241 (14)	C18—C19	1.3931 (14)
C1—C10	1.5270 (14)	C19—C20	1.3977 (14)
C1—C18	1.5442 (13)	C19—H19	0.9500
C1—H1	1.0000	C20—C21	1.4121 (14)
C2—C3	1.3654 (15)	C20—C24	1.5414 (14)
C2—C7	1.4479 (14)	C21—C22	1.4085 (14)
C3—C4	1.5015 (14)	C22—C23	1.4014 (14)
C4—C5	1.5329 (15)	C22—C28	1.5453 (13)
C4—H4A	0.9900	C23—H23	0.9500
C4—H4B	0.9900	C24—C25	1.5390 (14)
C5—C6	1.5262 (16)	C24—C26	1.5436 (16)
C5—C9	1.5305 (15)	C24—C27	1.5459 (16)
C5—C8	1.5329 (15)	C25—H25A	0.9800
C6—C7	1.5104 (15)	C25—H25B	0.9800
C6—H6A	0.9900	C25—H25C	0.9800
C6—H6B	0.9900	C26—H26A	0.9800
C8—H8A	0.9800	C26—H26B	0.9800
C8—H8B	0.9800	C26—H26C	0.9800
C8—H8C	0.9800	C27—H27A	0.9800
C9—H9A	0.9800	C27—H27B	0.9800
C9—H9B	0.9800	C27—H27C	0.9800
C9—H9C	0.9800	C28—C29	1.5373 (14)
C10—C11	1.3703 (14)	C28—C31	1.5423 (15)
C10—C15	1.4361 (14)	C28—C30	1.5429 (14)
C11—C12	1.5044 (14)	C29—H29A	0.9800
C12—C13	1.5332 (14)	C29—H29B	0.9800
C12—H12A	0.9900	C29—H29C	0.9800
C12—H12B	0.9900	C30—H30A	0.9800
C13—C16	1.5305 (15)	C30—H30B	0.9800
C13—C14	1.5338 (14)	C30—H30C	0.9800
C13—C17	1.5360 (15)	C31—H31A	0.9800
C14—C15	1.5098 (14)	C31—H31B	0.9800
C14—H14A	0.9900	C31—H31C	0.9800

C3—O1—H1O	111.9 (11)	H16A—C16—H16B	109.5
C11—O3—H3O	113.4 (11)	C13—C16—H16C	109.5
C21—O5—H5O	112.4 (12)	H16A—C16—H16C	109.5
C2—C1—C10	114.48 (8)	H16B—C16—H16C	109.5
C2—C1—C18	114.35 (8)	C13—C17—H17A	109.5
C10—C1—C18	113.17 (8)	C13—C17—H17B	109.5
C2—C1—H1	104.4	H17A—C17—H17B	109.5
C10—C1—H1	104.4	C13—C17—H17C	109.5
C18—C1—H1	104.4	H17A—C17—H17C	109.5
C3—C2—C7	117.84 (9)	H17B—C17—H17C	109.5
C3—C2—C1	124.54 (9)	C23—C18—C19	117.75 (9)
C7—C2—C1	117.58 (9)	C23—C18—C1	122.62 (9)
O1—C3—C2	124.54 (9)	C19—C18—C1	119.51 (9)
O1—C3—C4	112.67 (9)	C18—C19—C20	122.87 (9)
C2—C3—C4	122.78 (10)	C18—C19—H19	118.6
C3—C4—C5	113.58 (9)	C20—C19—H19	118.6
C3—C4—H4A	108.9	C19—C20—C21	117.18 (9)
C5—C4—H4A	108.9	C19—C20—C24	120.65 (9)
C3—C4—H4B	108.9	C21—C20—C24	122.14 (9)
C5—C4—H4B	108.9	O5—C21—C22	115.54 (9)
H4A—C4—H4B	107.7	O5—C21—C20	122.49 (9)
C6—C5—C9	110.09 (10)	C22—C21—C20	121.96 (9)
C6—C5—C4	106.73 (9)	C23—C22—C21	117.25 (9)
C9—C5—C4	111.35 (9)	C23—C22—C28	120.95 (9)
C6—C5—C8	110.61 (9)	C21—C22—C28	121.73 (9)
C9—C5—C8	108.47 (9)	C18—C23—C22	122.82 (9)
C4—C5—C8	109.60 (10)	C18—C23—H23	118.6
C7—C6—C5	113.92 (9)	C22—C23—H23	118.6
C7—C6—H6A	108.8	C25—C24—C20	111.64 (9)
C5—C6—H6A	108.8	C25—C24—C26	106.33 (9)
C7—C6—H6B	108.8	C20—C24—C26	109.60 (9)
C5—C6—H6B	108.8	C25—C24—C27	105.83 (9)
H6A—C6—H6B	107.7	C20—C24—C27	111.38 (9)
O2—C7—C2	121.33 (10)	C26—C24—C27	111.91 (9)
O2—C7—C6	118.45 (10)	C24—C25—H25A	109.5
C2—C7—C6	120.18 (10)	C24—C25—H25B	109.5
C5—C8—H8A	109.5	H25A—C25—H25B	109.5
C5—C8—H8B	109.5	C24—C25—H25C	109.5
H8A—C8—H8B	109.5	H25A—C25—H25C	109.5
C5—C8—H8C	109.5	H25B—C25—H25C	109.5
H8A—C8—H8C	109.5	C24—C26—H26A	109.5
H8B—C8—H8C	109.5	C24—C26—H26B	109.5
C5—C9—H9A	109.5	H26A—C26—H26B	109.5
C5—C9—H9B	109.5	C24—C26—H26C	109.5
H9A—C9—H9B	109.5	H26A—C26—H26C	109.5
C5—C9—H9C	109.5	H26B—C26—H26C	109.5
H9A—C9—H9C	109.5	C24—C27—H27A	109.5
H9B—C9—H9C	109.5	C24—C27—H27B	109.5
C11—C10—C15	117.13 (9)	H27A—C27—H27B	109.5
C11—C10—C1	121.77 (9)	C24—C27—H27C	109.5
C15—C10—C1	120.93 (8)	H27A—C27—H27C	109.5
O3—C11—C10	124.11 (9)	H27B—C27—H27C	109.5
O3—C11—C12	112.55 (8)	C29—C28—C31	107.37 (9)
C10—C11—C12	123.32 (9)	C29—C28—C30	106.28 (9)
C11—C12—C13	112.71 (8)	C31—C28—C30	110.04 (9)
C11—C12—H12A	109.1	C29—C28—C22	111.71 (8)
C13—C12—H12A	109.0	C31—C28—C22	109.34 (8)
C11—C12—H12B	109.0	C30—C28—C22	111.97 (8)
C13—C12—H12B	109.1	C28—C29—H29A	109.5
H12A—C12—H12B	107.8	C28—C29—H29B	109.5
C16—C13—C12	110.75 (9)	H29A—C29—H29B	109.5
C16—C13—C14	108.46 (9)	C28—C29—H29C	109.5
C12—C13—C14	107.76 (8)	H29A—C29—H29C	109.5
C16—C13—C17	108.58 (9)	H29B—C29—H29C	109.5
C12—C13—C17	110.09 (9)	C28—C30—H30A	109.5
C14—C13—C17	111.20 (8)	C28—C30—H30B	109.5
C15—C14—C13	115.84 (9)	H30A—C30—H30B	109.5
C15—C14—H14A	108.3	C28—C30—H30C	109.5
C13—C14—H14A	108.3	H30A—C30—H30C	109.5
C15—C14—H14B	108.3	H30B—C30—H30C	109.5
C13—C14—H14B	108.3	C28—C31—H31A	109.5
H14A—C14—H14B	107.4	C28—C31—H31B	109.5
O4—C15—C10	121.45 (9)	H31A—C31—H31B	109.5
O4—C15—C14	118.02 (9)	C28—C31—H31C	109.5
C10—C15—C14	120.51 (9)	H31A—C31—H31C	109.5
C13—C16—H16A	109.5	H31B—C31—H31C	109.5
C13—C16—H16B	109.5

C10—C1—C2—C3	−80.31 (12)	C11—C10—C15—O4	159.09 (10)
C18—C1—C2—C3	52.59 (13)	C1—C10—C15—O4	−16.20 (15)
C10—C1—C2—C7	97.16 (11)	C11—C10—C15—C14	−19.37 (14)
C18—C1—C2—C7	−129.95 (9)	C1—C10—C15—C14	165.34 (9)
C7—C2—C3—O1	−170.29 (10)	C13—C14—C15—O4	171.74 (9)
C1—C2—C3—O1	7.17 (16)	C13—C14—C15—C10	−9.75 (14)
C7—C2—C3—C4	10.96 (15)	C2—C1—C18—C23	14.42 (14)
C1—C2—C3—C4	−171.58 (9)	C10—C1—C18—C23	147.93 (10)
O1—C3—C4—C5	−156.69 (9)	C2—C1—C18—C19	−169.61 (9)
C2—C3—C4—C5	22.20 (15)	C10—C1—C18—C19	−36.10 (13)
C3—C4—C5—C6	−51.77 (12)	C23—C18—C19—C20	−2.46 (15)
C3—C4—C5—C9	68.40 (12)	C1—C18—C19—C20	−178.62 (9)
C3—C4—C5—C8	−171.58 (9)	C18—C19—C20—C21	−1.08 (15)
C9—C5—C6—C7	−69.22 (12)	C18—C19—C20—C24	−179.42 (10)
C4—C5—C6—C7	51.76 (13)	C19—C20—C21—O5	−175.48 (9)
C8—C5—C6—C7	170.91 (10)	C24—C20—C21—O5	2.84 (16)
C3—C2—C7—O2	166.72 (10)	C19—C20—C21—C22	3.91 (15)
C1—C2—C7—O2	−10.92 (15)	C24—C20—C21—C22	−177.77 (10)
C3—C2—C7—C6	−10.86 (15)	O5—C21—C22—C23	176.38 (9)
C1—C2—C7—C6	171.50 (9)	C20—C21—C22—C23	−3.06 (15)
C5—C6—C7—O2	159.86 (10)	O5—C21—C22—C28	−0.72 (14)
C5—C6—C7—C2	−22.50 (15)	C20—C21—C22—C28	179.85 (9)
C2—C1—C10—C11	−82.41 (12)	C19—C18—C23—C22	3.40 (15)
C18—C1—C10—C11	144.14 (9)	C1—C18—C23—C22	179.43 (9)
C2—C1—C10—C15	92.66 (11)	C21—C22—C23—C18	−0.72 (15)
C18—C1—C10—C15	−40.79 (12)	C28—C22—C23—C18	176.40 (10)
C15—C10—C11—O3	−167.64 (9)	C19—C20—C24—C25	−6.12 (15)
C1—C10—C11—O3	7.61 (15)	C21—C20—C24—C25	175.62 (10)
C15—C10—C11—C12	10.77 (15)	C19—C20—C24—C26	111.43 (11)
C1—C10—C11—C12	−173.97 (9)	C21—C20—C24—C26	−66.83 (13)
O3—C11—C12—C13	−155.18 (9)	C19—C20—C24—C27	−124.18 (10)
C10—C11—C12—C13	26.24 (14)	C21—C20—C24—C27	57.56 (13)
C11—C12—C13—C16	−169.61 (9)	C23—C22—C28—C29	8.36 (14)
C11—C12—C13—C14	−51.12 (11)	C21—C22—C28—C29	−174.66 (10)
C11—C12—C13—C17	70.30 (11)	C23—C22—C28—C31	−110.35 (11)
C16—C13—C14—C15	163.76 (9)	C21—C22—C28—C31	66.63 (12)
C12—C13—C14—C15	43.82 (12)	C23—C22—C28—C30	127.43 (10)
C17—C13—C14—C15	−76.92 (11)	C21—C22—C28—C30	−55.59 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O4	0.930 (19)	1.711 (19)	2.6201 (11)	164.7 (17)
O3—H3O···O2	0.950 (19)	1.68 (2)	2.6174 (11)	170.3 (17)
O5—H5O···O4ⁱ	0.848 (19)	2.128 (18)	2.8285 (11)	139.7 (16)
C14—H14A···O5ⁱⁱ	0.99	2.48	3.1912 (12)	128

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

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

H4B···H16B	2.39	x, 3/2 - y, 1/2 + z
H4A···H1	2.31	1 - x, 1/2 + y, 3/2 - z
H17B···O2	2.65	1 - x, 1 - y, 1 - z
O4···H5O	2.12	2 - x, 1/2 + y, 3/2 - z
C17···H30B	3.10	x, 1/2 - y, -1/2 + z
H26C···H6A	2.58	1 + x, y, z
H25B···H17A	2.57	2 - x, 1 - y, 1 - z

Acknowledgements

Authors' contributions are as follows. Conceptualization, ANK and IGM; methodology, ANK and IGM; investigation, ANK, MA and AB; writing (original draft), MA and ANK; writing (review and editing of the manuscript), MA and ANK; visualization, MA, ANK and IGM; funding acquisition, VNK, AB and ANK; resources, AB, VNK, RMR and LVA; supervision, ANK and MA.

Funding information

This paper was supported by Baku State University, UNEC and the RUDN University Strategic Academic Leadership Program.

References

Bolte, M., Degen, A. & Rühl, S. (1997a). Acta Cryst. C53, 340–342. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Bolte, M., Degen, A. & Rühl, S. (2001b). Acta Cryst. E57, o170–o171. Web of Science CSD CrossRef IUCr Journals Google Scholar
Çelik, M. S., Çetinus, A., Yenidünya, A. F., Çetinkaya, S. & Tüzün, B. (2023). J. Mol. Struct. 1272, 134158. Google Scholar
Cha, J. H., Cho, Y. S., Lee, J. K., Park, J. & Sato, H. (2012). Acta Cryst. E68, o2510. CSD CrossRef IUCr Journals Google Scholar
Cha, J. H., Kim, Y. H., Min, S.-J., Cho, Y. S. & Lee, J. K. (2011). Acta Cryst. E67, o3153. Web of Science CSD CrossRef IUCr Journals Google Scholar
Cha, J. H., Lee, J. K., Min, S.-J., Cho, Y. S. & Park, J. (2013a). Acta Cryst. E69, o1347. CSD CrossRef IUCr Journals Google Scholar
Cha, J. H., Min, S.-J., Cho, Y. S., Lee, J. K. & Park, J. (2013b). Acta Cryst. E69, o397. CSD CrossRef IUCr Journals Google Scholar
Chalkha, M., Ameziane el Hassani, A., Nakkabi, A., Tüzün, B., Bakhouch, M., Benjelloun, A. T., Sfaira, M., Saadi, M., Ammari, L. E. & Yazidi, M. E. (2023). J. Mol. Struct. 1273, 134255. Web of Science CSD CrossRef Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Gurbanov, A. V., Kuznetsov, M. L., Demukhamedova, S. D., Alieva, I. N., Godjaev, N. M., Zubkov, F. I., Mahmudov, K. T. & Pombeiro, A. J. L. (2020). CrystEngComm, 22, 628–633. 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
Khan, Z. & Sekar, N. (2022). Dyes Pigments, 208, 110735. Web of Science CrossRef Google Scholar
Lakhrissi, Y., Rbaa, M., Tuzun, B., Hichar, A., Anouar, H., Ounine, K., Almalki, F., Hadda, T. B., Zarrouk, A. & Lakhrissi, B. (2022). J. Mol. Struct. 1259, 132683. Web of Science CrossRef Google Scholar
Maharramov, A. M., Shikhaliyev, N. G., Zeynalli, N. R., Niyazova, A. A., Garazade, Kh. A. & Shikhaliyeva, I. M. (2021). UNEC J. Eng. Appl. Sci. 1, 5–11. Google Scholar
Maharramov, A. M., Suleymanova, G. T., Qajar, A. M., Niyazova, A. A., Ahmadova, N. E., Shikhaliyeva, I. M., Garazade, Kh. A., Nenajdenko, V. G. & Shikaliyev, N. G. (2022). UNEC J. Eng. Appl. Sci. 2, 64–73. Google Scholar
Maia, M., Resende, D. I. S. P., Durães, F., Pinto, M. M. M. & Sousa, E. (2021). Eur. J. Med. Chem. 210, 113085. Web of Science CrossRef PubMed Google Scholar
Majumdar, D., Philip, J. E., Tüzün, B., Frontera, A., Gomila, R. M., Roy, S. & Bankura, K. (2022). J. Inorg. Organomet. Polym. 32, 4320–4339. Web of Science CrossRef CAS Google Scholar
Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England. 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
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Steiger, S. A., Li, C., Gates, C. & Natale, N. R. (2020). Acta Cryst. E76, 125–131. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sughanya, V. & Sureshbabu, N. (2012). Acta Cryst. E68, o2875–o2876. CSD CrossRef CAS IUCr Journals Google Scholar
Sureshbabu, N. & Sughanya, V. (2012). Acta Cryst. E68, o2638. CSD CrossRef IUCr Journals Google Scholar
Tapera, M., Kekeçmuhammed, H., Tüzün, B., Sarıpınar, E., Koçyiğit, M., Yıldırım, E., Doğan, M. & Zorlu, Y. (2022). J. Mol. Struct. 1269, 133816. Web of Science CSD CrossRef Google Scholar
Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). CrystalExplorer17. The University of Western Australia. Google Scholar
Zhu, Y.-L., Xiao, G.-L., Chen, Y.-F., Chen, R.-T. & Zhou, Y. (2011). Acta Cryst. E67, o2398. Web of Science CSD CrossRef IUCr Journals 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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