Synthesis, crystal structure and Hirshfeld surface analysis of ethyl (E)-2-cyano-3-[5-(4-ethyl­phen­yl)isoxazol-3-yl]prop-2-enoate

Kolesnik, I.A.; Sanchez-Pimentel, A.P.; Grigoriev, M.S.; Hökelek, T.; Hasanov, K.I.; Guliyeva, N.A.; Javadzade, T.A.; Al-Douh, M.H.

doi:10.1107/S2056989025006875

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ISSN: 2056-9890

Volume 81| Part 9| September 2025| Pages 857-860

https://doi.org/10.1107/S2056989025006875

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Synthesis, crystal structure and Hirshfeld surface analysis of ethyl (E)-2-cyano-3-[5-(4-ethylphenyl)isoxazol-3-yl]prop-2-enoate

Irina A. Kolesnik,^a Artem P. Sanchez-Pimentel,^b Mikhail S. Grigoriev,^c Tuncer Hökelek,^d Khudayar I. Hasanov,^e Narmina A. Guliyeva,^f Tahir A. Javadzade ^g and Mohammed Hadi Al-Douh ^h ^*

^aInstitute of Physical Organic Chemistry of National Academy of Sciences of Belarus, 13 Surganov Str., 220072 Minsk, Belarus, ^bFaculty of Science, RUDN University, 6 Miklukho-Maklaya Str., 117198 Moscow, Russian Federation, ^cFrumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 31 Bldg 4, Leninsky prosp, 119071 Moscow, Russian Federation, ^dHacettepe University, Department of Physics, 06800 Beytepe-Ankara, Türkiye, ^eAzerbaijan Medical University, Scientific Research Centre (SRC), A. Kasumzade Str. 14, AZ1022, Baku, Azerbaijan, ^fBaku Engineering University, Khirdalan, Hasan Aliyev Str. 120, AZ0101, Absheron, Azerbaijan, ^gDepartment of Chemistry and Chemical Engineering, Khazar University, Mahsati Str. 41, AZ1096, Baku, Azerbaijan, and ^hChemistry Department, Faculty of Science, Hadhramout University, Mukalla, Hadhramout, Yemen
^*Correspondence e-mail: [email protected]

Edited by J. Ellena, Universidade de Sâo Paulo, Brazil (Received 11 July 2025; accepted 31 July 2025; online 19 August 2025)

In the molecule of the title compound, C₁₇H₁₆N₂O₃, the isoxazol and phenyl rings are oriented at a dihedral angle of 14.84 (5)°. The 2-cyanoacrylate moiety is in E- configuration. In the crystal, there are no intermolecular hydrogen-bonding or C—H⋯π(ring) interactions, only a π–π interaction between the parallel isoxazol rings with centroid-to-centroid distance of 3.4932 (9) Å (α = 0.02°). The Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (43.9%), H⋯N/N⋯H (17.0%), H⋯O/O⋯H (13.9%) and C⋯C (10.1%) interactions.

Keywords: crystal structure; isoxazole ring; cyanoacrylaate; Hirshfeld surface analysis.

CCDC reference: 2477570

1. Chemical context

Esters of cyanoacrylic acid – cyanoacrylates – are well-known to be the components of adhesive compositions. They are also convenient and versatile building blocks in organic synthesis that are widely used in processes of carbon skeleton growth (Ammida & Giath, 2003 ; Kim et al., 2005 ; Motokura et al., 2019 ). They have found wide applications in the syntheses of cyclic and heterocyclic structures, including condensed derivatives. In particular, they are used to obtain polysubstituted cyclopropanes (Zhang et al., 2017 ), cyclohexenes (Xiao et al., 2012 ), cyanoanilines (Sharanin et al., 1980 ), chromenes (Dong et al., 2010 ; Chang et al., 2021 ), pyranocoumarines (Xie et al., 2022 ), pyrrolidines (Imagawa et al., 2016 ), tetrahydrofurans (Khan et al., 2014 ), pyrimidines (Moirangthem & Laitonjam, 2009 ; Sheibani et al., 2009 ), piperidines (Dong et al., 2021 ) and others. The most commonly used substrates are 3-aryl and 3-hetaryl 2-cyanoacrylates. As a result of the asymmetry of the spatial structure of the molecule, they can exist in the form of Z- and E-isomers, which can ultimately affect the spatial structure of the products resulting from the reactions with their participation. The configuration of the trisubstituted double bond of cyanoacrylates depends on the synthesis conditions and structure of the substrates (Irfan et al., 2021 ). This determines the importance of accurately establishing the crystal structure of cyanoacrylates. Herein, we report on the crystal structure of ethyl (E)-2-cyano-3-[5-(4-ethylphenyl)isoxazol-3-yl]prop-2-enoate (1), which we studied as a starting compound for the synthesis of isoxazole-containing pyrans and chromenes (Potkin et al., 2024 ). According to literature data, similar in structure aryl and hetaryl cyanoacrylates also have the E-configuration of the exocyclic double bond (Deshpande et al., 2012 ; Franconetti et al., 2016 ; Kalkhambkar et al., 2012 ).

2. Structural commentary

The asymmetric unit of the title compound, C₁₇H₁₆N₂O₃, contains isoxazol (O1/N2/C3–C5) and phenyl (C11–C16) rings oriented at a dihedral angle of 14.84 (5)° (Fig. 1). The corresponding dihedral angles are reported to be 46.22 (4)° in C₁₇H₁₃NO₃ (Benouatas et al., 2021 ) and 5.50 (8)° in C₁₇H₁₃NO₂ (Asiri et al., 2012 ). Atoms C1, C6, C7, N1 and C17 are located 0.0178 (18), 0.0389 (15), 0.0641 (15), −0.044 (2) and −0.0429 (15) Å, respectively, away from the corresponding ring planes. In the ethyl 2-cyanoacrylate moiety, the C9—O3—C8—C7, O3—C8—C7—C6, C8—C7—C6—C3 and C7—C6—C3—N2 torsion angles are −179.66 (12), 175.16 (13), −177.75 (12) and 179.15 (14)°, respectively, showing an E-configuration. Bond lengths and angles agree well with the values observed for the related compounds (Z)-4-(2-methoxybenzylidene)-3-phenylisoxazol-5(4H)-one (Benouatas et al., 2021) and (4Z)-4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one (Asiri et al., 2012).

Figure 1
The asymmetric unit of the title compound with atom-numbering scheme and 50% probability ellipsoids.

3. Supramolecular features

In the crystal, the molecules are stacked along the a-axis direction (Fig. 2) and there are no intermolecular hydrogen-bonding or C—H⋯π(ring) interactions, only a π–π interaction between the parallel isoxazol (O1/N2/C3–C5) rings with a centroid-to-centroid distance of 3.4932 (9) Å (α = 0.02°).

Figure 2
A partial packing diagram for the title compound viewed down the c-axis direction.

4. Hirshfeld surface analysis

To visualize the intermolecular interactions in the crystal of title compound, a Hirshfeld surface (HS) analysis was carried out using Crystal Explorer 17.5 (Spackman et al., 2021 ). In the HS plotted over d_norm (Fig. 3), the white surface indicates contacts with distances equal to the sum of van der Waals radii, and the red and blue colours indicate distances shorter (in close contact) or longer (distinct contact) than the van der Waals radii, respectively (Table 1) (Venkatesan et al., 2016 ). The appearing bright-red spots indicate their roles as the respective donors and/or acceptors. The shape-index surface can be used to identify characteristic packing modes, in particular, planar stacking arrangements and the presence of aromatic stacking interactions such as C—H⋯π and π–π interactions with the former represented as red π-holes, which are related to the electron ring interactions between the C–H groups with the centroid of the aromatic rings of neighbouring molecules. Fig. 4 clearly suggests that there are no C—H⋯π interactions. π–π stacking is indicated by the presence of adjacent red and blue triangles; if there are no adjacent red and/or blue triangles, then there are no π–π interactions. Fig. 4 clearly suggests that there are π⋯π interactions in the title compound. According to the two-dimensional fingerprint plots (Fig. 5), H⋯H (43.9%), H⋯N/N⋯H (17.0%), H⋯O/O⋯H (13.9%) and C⋯C (10.1%) contacts make the most important contributions to the HS.

Table 1
Selected interatomic distances (Å)

O1⋯H12	2.52	C1⋯C4	3.069 (2)
O1⋯H9Aⁱ	2.66	C3⋯C11^iv	3.403 (2)
O2⋯H9B	2.38	C6⋯C11^iv	3.385 (2)
O2⋯H15ⁱⁱ	2.61	C6⋯C16^iv	3.404 (2)
O2⋯H6	2.48	C1⋯H4	2.63
N1⋯H13ⁱⁱⁱ	2.65	C4⋯H16	2.82
N1⋯H4	2.65	H13⋯H17A	2.37
N2⋯H9Aⁱ	2.69
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

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

Figure 4
The shape-index surface showing two orientations.

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

5. Synthesis and crystallization

Compound 1 was obtained according to the method (Fig. 6) described by us earlier (Potkin et al., 2024). 5-(4-Ethylphenyl)isoxazole-3-carbaldehyde (2) (0.50 g, 2.5 mmol) and ethyl cyanoacetate (0.34 g, 3.0 mmol) were dissolved in EtOH (10 ml), 2 drops of piperidine were added and the resulting mixture was stirred for 5 h at 323 K then kept at 278 K overnight. The resulting precipitate was filtered, washed with cold EtOH (2 × 5 ml) and dried under reduced pressure. The obtained product did not require further purification. It was crystallized from methanol solution to give pale creamy needles, yield 0.50 g (67%), m.p. 274–276 K. IR (KBr), ν (cm⁻¹): 2232 (CN), 1737 (C=O), 1663, 1613, 1592, 1561 (1,2-oxazole), 1245 (aromatic C–H), 797 (vinylene –CH=), 534 (–CH=C—CN). ¹H NMR (CDCl₃, 500 MHz, 301 K): δ = 7.95 (s, 1H, –CH=), 7.75 (d, 2H, HAr, J = 8.4), 7.37 (s, 1H, H4), 7.32 (d, 2H, H Ar, J = 8.4), 4.42 (q, 2H, CH₂, J = 7.1), 2.71 (q, 2H, CH₂, J = 7.6), 1.41 (t, 3H, CH₃, J = 7.1), 1.27 (t, 3H, CH₃, J = 7.6). ¹³C NMR (CDCl₃, 125 MHz, 301 K): δ = 172.6, 161.0, 157.9, 147.9, 142.8, 128.8 (2C), 124.0, 114.2, 109.8, 97.6, 63.5, 29.0, 15.4, 14.2. MS (APCI): m/z = 296 [M]⁺ (100).

Figure 6
Reaction scheme.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The C-bound hydrogen-atom positions were calculated geometrically at distances of 0.95 Å (for aromatic CH), 0.99 Å (for CH₂) and 0.98 Å (for CH₃), and refined using a riding model applying the constraint U_iso = k × U_eq (C), where k = 1.5 for methyl hydrogens and k = 1.2 for all other hydrogen atoms.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₆N₂O₃
M_r	296.32
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	100
a, b, c (Å)	7.2361 (6), 10.1537 (8), 11.1493 (8)
α, β, γ (°)	73.098 (2), 76.611 (3), 72.555 (3)
V (Å³)	738.32 (10)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.32 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.930, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13453, 4283, 3544
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.150, 1.02
No. of reflections	4283
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.74, −0.62
Computer programs: APEX3 and SAINT (Bruker, 2014 ), SHELXT2019/1 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ) and SHELXTL (Sheldrick, 2008 ).

Supporting information

CCDC reference: 2477570

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989025006875/ex2093sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025006875/ex2093Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989025006875/ex2093Isup3.cml

checkCIF report

Computing details top

Ethyl (E)-2-cyano-3-[5-(4-ethylphenyl)isoxazol-3-yl]prop-2-enoate top

Crystal data top

C₁₇H₁₆N₂O₃	Z = 2
M_r = 296.32	F(000) = 312
Triclinic, P1	D_x = 1.333 Mg m⁻³
a = 7.2361 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1537 (8) Å	Cell parameters from 5551 reflections
c = 11.1493 (8) Å	θ = 2.5–30.1°
α = 73.098 (2)°	µ = 0.09 mm⁻¹
β = 76.611 (3)°	T = 100 K
γ = 72.555 (3)°	Bulk, colourless
V = 738.32 (10) Å³	0.40 × 0.32 × 0.20 mm

Data collection top

Bruker Kappa APEXII diffractometer	3544 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.020
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 30.0°, θ_min = 3.8°
T_min = 0.930, T_max = 1.000	h = −8→10
13453 measured reflections	k = −14→14
4283 independent reflections	l = −15→15

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.055	H-atom parameters constrained
wR(F²) = 0.150	w = 1/[σ²(F_o²) + (0.073P)² + 0.5251P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
4283 reflections	Δρ_max = 0.74 e Å⁻³
201 parameters	Δρ_min = −0.62 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	0.28675 (16)	0.69298 (11)	0.44138 (9)	0.0194 (2)
O2	0.30302 (17)	0.26261 (11)	0.13160 (10)	0.0219 (2)
O3	0.27135 (18)	0.07239 (11)	0.29464 (10)	0.0234 (2)
N1	0.1827 (3)	0.14647 (16)	0.57881 (14)	0.0370 (4)
N2	0.2963 (2)	0.63165 (13)	0.34260 (11)	0.0200 (3)
C1	0.2185 (2)	0.20516 (16)	0.47481 (14)	0.0229 (3)
C3	0.26948 (19)	0.50293 (14)	0.39795 (13)	0.0152 (3)
C4	0.24135 (19)	0.47687 (14)	0.53287 (13)	0.0154 (3)
H4	0.219017	0.393425	0.593852	0.018*
C5	0.25385 (19)	0.59890 (14)	0.55416 (13)	0.0148 (3)
C6	0.27883 (19)	0.41529 (14)	0.31311 (13)	0.0156 (3)
H6	0.301540	0.457438	0.224765	0.019*
C7	0.2590 (2)	0.28166 (14)	0.34550 (13)	0.0159 (3)
C8	0.2809 (2)	0.20658 (14)	0.24319 (13)	0.0166 (3)
C9	0.2914 (3)	−0.01480 (16)	0.20686 (16)	0.0273 (3)
H9A	0.212681	−0.085624	0.245866	0.033*
H9B	0.241248	0.046024	0.128222	0.033*
C10	0.4965 (3)	−0.0876 (2)	0.1760 (2)	0.0374 (4)
H10A	0.572276	−0.017378	0.130783	0.056*
H10B	0.507173	−0.151209	0.121968	0.056*
H10C	0.548105	−0.143216	0.254400	0.056*
C11	0.24115 (19)	0.64417 (14)	0.66934 (12)	0.0147 (3)
C12	0.2177 (2)	0.78675 (15)	0.66627 (13)	0.0165 (3)
H12	0.208358	0.856744	0.588440	0.020*
C13	0.2081 (2)	0.82569 (15)	0.77770 (13)	0.0180 (3)
H13	0.192322	0.922782	0.774977	0.022*
C14	0.2212 (2)	0.72541 (15)	0.89328 (13)	0.0181 (3)
C15	0.2458 (2)	0.58249 (16)	0.89528 (13)	0.0198 (3)
H15	0.255225	0.512582	0.973156	0.024*
C16	0.2564 (2)	0.54221 (15)	0.78484 (13)	0.0178 (3)
H16	0.274169	0.444908	0.787414	0.021*
C17	0.2048 (3)	0.76846 (17)	1.01452 (14)	0.0244 (3)
H17A	0.213608	0.868262	0.993749	0.029*
H17B	0.316062	0.708018	1.058750	0.029*
C18	0.0129 (3)	0.7546 (2)	1.10285 (16)	0.0313 (4)
H18A	−0.097706	0.812084	1.058595	0.047*
H18B	0.005407	0.788052	1.178329	0.047*
H18C	0.007697	0.654765	1.128448	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0318 (6)	0.0145 (5)	0.0139 (5)	−0.0080 (4)	−0.0037 (4)	−0.0041 (4)
O2	0.0335 (6)	0.0191 (5)	0.0158 (5)	−0.0097 (4)	−0.0050 (4)	−0.0038 (4)
O3	0.0413 (6)	0.0133 (5)	0.0183 (5)	−0.0077 (4)	−0.0089 (4)	−0.0034 (4)
N1	0.0710 (12)	0.0230 (7)	0.0202 (7)	−0.0198 (7)	−0.0045 (7)	−0.0038 (5)
N2	0.0323 (7)	0.0165 (6)	0.0140 (5)	−0.0083 (5)	−0.0042 (5)	−0.0052 (4)
C1	0.0364 (8)	0.0162 (6)	0.0184 (7)	−0.0089 (6)	−0.0048 (6)	−0.0050 (5)
C3	0.0167 (6)	0.0147 (6)	0.0147 (6)	−0.0038 (4)	−0.0032 (4)	−0.0036 (5)
C4	0.0185 (6)	0.0147 (6)	0.0139 (6)	−0.0060 (5)	−0.0017 (5)	−0.0037 (5)
C5	0.0160 (6)	0.0142 (6)	0.0137 (6)	−0.0041 (4)	−0.0020 (4)	−0.0026 (5)
C6	0.0176 (6)	0.0153 (6)	0.0146 (6)	−0.0043 (5)	−0.0030 (5)	−0.0041 (5)
C7	0.0184 (6)	0.0159 (6)	0.0147 (6)	−0.0045 (5)	−0.0037 (5)	−0.0043 (5)
C8	0.0197 (6)	0.0138 (6)	0.0176 (6)	−0.0038 (5)	−0.0051 (5)	−0.0045 (5)
C9	0.0466 (10)	0.0154 (7)	0.0241 (7)	−0.0066 (6)	−0.0131 (7)	−0.0067 (6)
C10	0.0396 (10)	0.0355 (10)	0.0414 (10)	−0.0102 (8)	−0.0068 (8)	−0.0145 (8)
C11	0.0158 (6)	0.0149 (6)	0.0148 (6)	−0.0053 (4)	−0.0025 (4)	−0.0041 (5)
C12	0.0198 (6)	0.0146 (6)	0.0156 (6)	−0.0053 (5)	−0.0034 (5)	−0.0029 (5)
C13	0.0235 (6)	0.0155 (6)	0.0171 (6)	−0.0079 (5)	−0.0019 (5)	−0.0047 (5)
C14	0.0224 (6)	0.0202 (7)	0.0147 (6)	−0.0101 (5)	−0.0008 (5)	−0.0054 (5)
C15	0.0269 (7)	0.0190 (6)	0.0139 (6)	−0.0093 (5)	−0.0028 (5)	−0.0011 (5)
C16	0.0225 (6)	0.0148 (6)	0.0167 (6)	−0.0072 (5)	−0.0024 (5)	−0.0026 (5)
C17	0.0389 (8)	0.0253 (7)	0.0151 (6)	−0.0173 (6)	−0.0023 (6)	−0.0057 (5)
C18	0.0311 (8)	0.0440 (10)	0.0187 (7)	−0.0055 (7)	−0.0023 (6)	−0.0126 (7)

Geometric parameters (Å, º) top

O1—C5	1.3600 (16)	C10—H10B	0.9800
O1—N2	1.3940 (15)	C10—H10C	0.9800
O2—C8	1.2033 (17)	C11—C12	1.3973 (18)
O3—C8	1.3319 (17)	C11—C16	1.4016 (18)
O3—C9	1.4573 (18)	C12—C13	1.3907 (19)
N1—C1	1.148 (2)	C12—H12	0.9500
N2—C3	1.3244 (18)	C13—C14	1.3935 (19)
C1—C7	1.434 (2)	C13—H13	0.9500
C3—C4	1.4260 (18)	C14—C15	1.402 (2)
C3—C6	1.4542 (18)	C14—C17	1.507 (2)
C4—C5	1.3594 (18)	C15—C16	1.385 (2)
C4—H4	0.9500	C15—H15	0.9500
C5—C11	1.4602 (18)	C16—H16	0.9500
C6—C7	1.3417 (19)	C17—C18	1.523 (2)
C6—H6	0.9500	C17—H17A	0.9900
C7—C8	1.5023 (19)	C17—H17B	0.9900
C9—C10	1.456 (3)	C18—H18A	0.9800
C9—H9A	0.9900	C18—H18B	0.9800
C9—H9B	0.9900	C18—H18C	0.9800
C10—H10A	0.9800

O1···H12	2.52	C1···C4	3.069 (2)
O1···H9Aⁱ	2.66	C3···C11^iv	3.403 (2)
O2···H9B	2.38	C6···C11^iv	3.385 (2)
O2···H15ⁱⁱ	2.61	C6···C16^iv	3.404 (2)
O2···H6	2.48	C1···H4	2.63
N1···H13ⁱⁱⁱ	2.65	C4···H16	2.82
N1···H4	2.65	H13···H17A	2.37
N2···H9Aⁱ	2.69

C5—O1—N2	109.17 (10)	H10A—C10—H10C	109.5
C8—O3—C9	116.59 (12)	H10B—C10—H10C	109.5
C3—N2—O1	105.59 (11)	C12—C11—C16	119.36 (12)
N1—C1—C7	178.45 (18)	C12—C11—C5	121.30 (12)
N2—C3—C4	111.53 (12)	C16—C11—C5	119.33 (12)
N2—C3—C6	115.97 (12)	C13—C12—C11	119.68 (13)
C4—C3—C6	132.48 (13)	C13—C12—H12	120.2
C5—C4—C3	104.09 (12)	C11—C12—H12	120.2
C5—C4—H4	128.0	C12—C13—C14	121.44 (13)
C3—C4—H4	128.0	C12—C13—H13	119.3
C4—C5—O1	109.62 (12)	C14—C13—H13	119.3
C4—C5—C11	133.27 (12)	C13—C14—C15	118.46 (13)
O1—C5—C11	117.11 (11)	C13—C14—C17	121.33 (13)
C7—C6—C3	127.35 (13)	C15—C14—C17	120.20 (13)
C7—C6—H6	116.3	C16—C15—C14	120.67 (13)
C3—C6—H6	116.3	C16—C15—H15	119.7
C6—C7—C1	122.94 (13)	C14—C15—H15	119.7
C6—C7—C8	119.39 (12)	C15—C16—C11	120.38 (13)
C1—C7—C8	117.67 (12)	C15—C16—H16	119.8
O2—C8—O3	126.28 (13)	C11—C16—H16	119.8
O2—C8—C7	123.60 (12)	C14—C17—C18	112.18 (13)
O3—C8—C7	110.12 (12)	C14—C17—H17A	109.2
C10—C9—O3	110.18 (14)	C18—C17—H17A	109.2
C10—C9—H9A	109.6	C14—C17—H17B	109.2
O3—C9—H9A	109.6	C18—C17—H17B	109.2
C10—C9—H9B	109.6	H17A—C17—H17B	107.9
O3—C9—H9B	109.6	C17—C18—H18A	109.5
H9A—C9—H9B	108.1	C17—C18—H18B	109.5
C9—C10—H10A	109.5	H18A—C18—H18B	109.5
C9—C10—H10B	109.5	C17—C18—H18C	109.5
H10A—C10—H10B	109.5	H18A—C18—H18C	109.5
C9—C10—H10C	109.5	H18B—C18—H18C	109.5

C5—O1—N2—C3	−0.13 (15)	C1—C7—C8—O3	−4.46 (18)
O1—N2—C3—C4	0.20 (15)	C8—O3—C9—C10	91.16 (17)
O1—N2—C3—C6	−178.31 (11)	C4—C5—C11—C12	−166.21 (15)
N2—C3—C4—C5	−0.19 (16)	O1—C5—C11—C12	14.54 (19)
C6—C3—C4—C5	177.99 (14)	C4—C5—C11—C16	15.0 (2)
C3—C4—C5—O1	0.10 (15)	O1—C5—C11—C16	−164.26 (12)
C3—C4—C5—C11	−179.19 (14)	C16—C11—C12—C13	−0.6 (2)
N2—O1—C5—C4	0.02 (15)	C5—C11—C12—C13	−179.36 (12)
N2—O1—C5—C11	179.44 (11)	C11—C12—C13—C14	−0.1 (2)
N2—C3—C6—C7	179.15 (14)	C12—C13—C14—C15	0.4 (2)
C4—C3—C6—C7	1.0 (2)	C12—C13—C14—C17	−178.16 (13)
C3—C6—C7—C1	1.9 (2)	C13—C14—C15—C16	−0.1 (2)
C3—C6—C7—C8	−177.75 (12)	C17—C14—C15—C16	178.47 (14)
C9—O3—C8—O2	0.6 (2)	C14—C15—C16—C11	−0.5 (2)
C9—O3—C8—C7	−179.66 (12)	C12—C11—C16—C15	0.9 (2)
C6—C7—C8—O2	−5.0 (2)	C5—C11—C16—C15	179.68 (13)
C1—C7—C8—O2	175.34 (14)	C13—C14—C17—C18	109.02 (16)
C6—C7—C8—O3	175.16 (13)	C15—C14—C17—C18	−69.51 (19)

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

Acknowledgements

The authors' contributions are as follows. Conceptualization, TH and MHAD; synthesis, IAK and APSP; NMR analysis, MSG and KIH; X-ray analysis, MSG and NAG; Hirshfeld surface analysis, TH; writing (review and editing of the manuscript), TH and MHAD; funding acquisition, KIH, NAG and TAJ; supervision, TH and MHAD.

Funding information

This publication has been supported by the Russian Science Foundation (project No. 23–43-10024) (APSP) and the Belarusian Republican Foundation for Fundamental Research (project No. X23RNF-051) (IAK). KIH, NAG and TAJ thank Azerbaijan Medical University, Baku Engineering University and Khazar University, respectively. TH is grateful to Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004).

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