Crystal structure and Hirshfeld surface analysis of 3-(4-meth­oxy­phen­yl)-2-[(thio­phen-2-yl)carbon­yl]acrylo­nitrile

Huseynov, E.Z.; Safarova, A.S.; Naghiyev, F.N.; Kurbanova, M.M.; Akkurt, M.; Ashurov, J.M.; Hamouda, H.A.; Mamedov, İ.G.

doi:10.1107/S205698902601042X

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Volume 82| Part 11| November 2026|

https://doi.org/10.1107/S205698902601042X

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Crystal structure and Hirshfeld surface analysis of 3-(4-methoxyphenyl)-2-[(thiophen-2-yl)carbonyl]acrylonitrile

Elnur Z. Huseynov,^a Ayten S. Safarova,^a Farid N. Naghiyev,^a Malahat M. Kurbanova,^a Mehmet Akkurt,^b Jamshid M. Ashurov,^c Hamouda Adam Hamouda ^d ^* and İbrahim G. Mamedov ^a

^aFaculty of Chemistry, Baku State University, Z. Khalilov str. 23, Az 1148, Baku, Azerbaijan, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye, ^cInstitute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, M. Ulugbek Str. 83, Tashkent 100125, Uzbekistan, and ^dDepartment of Chemistry, Faculty of Science, University of Kordofan, Sudan
^*Correspondence e-mail: [email protected]

Edited by X. Hao, Institute of Chemistry, Chinese Academy of Sciences (Received 1 October 2026; accepted 9 October 2026; online 13 October 2026)

In the title compound, C₁₅H₁₁NO₂S, the intramolecular C—H⋯O hydrogen-bond interaction forms an S(6) ring motif. The dihedral angle between the planes of the thiophene and methoxyphenyl ringss 12.26 (15)°. In the crystal, molecular pairs are joined by C—H⋯N contacts, forming R₂²(16) motifs lying parallel to the (001) plane. They are connected by C—O⋯π and π–π interactions [centroid-to-centroid lengths = 3.9049 (18) and 3.9050 (18) Å], resulting in layers parallel to the (100) plane. These layers are linked by C—H⋯N interactions. Hirshfeld surface analysis indicates that H⋯H (35.3%), O⋯H/H⋯O (13.5%), C⋯C (12.5%), N⋯H/H⋯N (11.6%), C⋯H/H⋯C (11.6%) and S⋯H/H⋯S (9.0%) interactions make significant contributions.

Keywords: crystal structure; Knoevenagel condensation reaction; C—H⋯N interaction; Hirshfeld surface analysis.

CCDC reference: 2594032

1. Chemical context

Knoevenagel condensation reactions play a significant role in carbon–carbon bond formation, providing a versatile strategy for the synthesis of α-functionalized chalcone analogues and other conjugated molecular frameworks (Naghiyev et al., 2023 ; Mamedov & Khalilov, 2025 ; Abdullayeva et al., 2026 ). Depending on the substrates and reaction conditions, these transformations can proceed under relatively mild conditions and afford products in good yields, sometimes with high stereoselectivity (Khalilov et al., 2011 ; Khalilov et al.,2023 ; Tüzün et al., 2025 ). Knoevenagel adducts have also been used as intermediates in the synthesis of compounds investigated in medicinal chemistry and materials research (Naghiyev et al., 2022 ; Naghiyev et al., 2024 ; Karimli et al., 2023 ). Among these chalcone analogues, α,β-unsaturated nitrile derivatives are of particular interest because their structural diversity and reactive functional groups allow further synthetic transformations (Akkurt et al., 2018 ; Asgarova et al., 2019 ; Shikhaliyev et al., 2025 ). Compounds combining a thiophene ring with an α,β-unsaturated carbonyl group and a nitrile group provide substrates for such transformations. In particular, thiophene-2-carbonyl-substituted acrylonitriles have been used in the synthesis of heterocyclic compounds.

In the present study, 3-oxo-3-(thiophen-2-yl)propanenitrile was reacted with 4-methoxybenzaldehyde in methanol at room temperature to afford the title compound (Fig. 1) and we now describe its structure. N-Methylpiperazine served as a base, facilitating condensation at the activated methylene group, followed by elimination of water. In this context, we report the crystal structure and Hirshfeld surface analysis of 3-(4-methoxyphenyl)-2-[(thiophen-2-yl)carbonyl]acrylonitrile as part of our ongoing investigations (Askerov et al., 2020 ; Naghiyev et al., 2021 ).

Figure 1
Synthesis of the title compound by Knoevenagel condensation.

2. Structural commentary

The intramolecular C8—H8⋯O1 hydrogen-bond interaction forms an S(6) ring motif in the molecule (Table 1 and Fig. 2; Bernstein et al., 1995 ). The dihedral angle between the planes of the thiophene ring (S1/C1–C4) and the methoxyphenyl ring (C9–C14) is 12.26 (15)°. The S1—C4—C5—C6, S1—C4—C5—O1, O1—C5—C6—C7, C7—C6—C8—C9 and C6—C8—C9—C14 torsion angles are 4.4 (5), 4.9 (4), −3.1 (5)° and −13.9 (5)°, respectively.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1	0.93	2.40	2.779 (3)	104
C13—H13⋯N1ⁱ	0.93	2.51	3.394 (4)	158
Symmetry code: (i) .

Figure 2
The molecular structure showing the atomic labelling. Displacement ellipsoids are drawn at the 50% probability level. The intramolecular C8—H8⋯O1 hydrogen bond is shown as a dashed line.

3. Supramolecular features and Hirshfeld surface analysis

In the crystal, molecular pairs are linked by C13—H13⋯N1 contacts, which form R₂²(16) motifs lying parallel to the (001) plane (Fig. 3). They are connected by the C—O⋯π contact [C5—O1⋯Cg1^a: C5—O1 = 1.226 (3) Å, O1⋯Cg1^a = 3.721 (3) Å, C5⋯Cg1^a = 3.602 (3) Å and C5—O1⋯Cg1^a = 74.94 (17)°; symmetry code: (a) x, −y + $[1 \over 2]$ , z − $[1 \over 2]$ ; Cg1 is the centroid of the S1/C1–C4 thiophene ring] and weak π–π interactions [Cg2⋯Cg2^b = 3.9049 (18) Å, slippage = 0.857 Å, Cg2⋯Cg2^c = 3.9050 (18) Å, slippage = 1.751 Å; symmetry codes: (b) x, −y + $[3 \over 2]$ , z − $[1 \over 2]$ ; (c) x, −y + $[3 \over 2]$ , z + $[1 \over 2]$ ; Cg2 is the centroid of the C9–C14 methoxyphenyl ring], producing layers parallel to the (100) plane. These layers are linked by C13—H13⋯N1 interactions (Fig. 4).

Figure 3
(a) A view of the C—H⋯N interactions in the unit cell. (b) A view down the b axis of the C—H⋯N interactions (dashed lines) for the situation shown in part (a). The R₂²(16) graph-set motif formed by a pair of C—H⋯N interactions. [Symmetry code: (i) −x + 1, −y + 1, −z + 1.]

Figure 4
(a) A view of the C—O⋯π and π–π interactions (dashed lines) along the a axis. (b) A view of the C—H⋯N, C—O⋯π and π–π interactions (dashed lines) along the b axis. For clarity, H atoms not involved in hydrogen bonding have been omitted.

In order to further characterize and quantify the intermolecular interactions in the title compound, a Hirshfeld surface analysis was carried out using CrystalExplorer21 (Spackman et al., 2021 ). The Hirshfeld surface mapped over d_norm is illustrated in Fig. 5(a). The d_norm mappings ranged from −0.20 to +1.26 a.u. The shape index [Fig. 5(b)] shows paired red–blue regions typical of π–π stacking, with an additional weak signal in the area of the aromatic ring–O contact.

Figure 5
Hirshfeld surface of the title compound, mapped over (a) d_norm and (b) shape index, showing the intermolecular C13—H13⋯N1 contacts.

The fingerprint plots provide quantitative information about the noncovalent interactions in the crystal packing in terms of the percentage contribution of the interatomic contacts. The fingerprint plots (Fig. 6) show that H⋯H interactions (35.3%) contribute the most to surface contacts. Other notable interactions include O⋯H/H⋯O (13.5%), C⋯C (12.5%), N⋯H/H⋯N (11.6%), C⋯H/H⋯C (11.6%) and S⋯H/H⋯S (9.0%). Less significant interactions include S⋯O/O⋯S (1.2%) and O⋯N/N⋯O (0.4%).

Figure 6
The two-dimensional fingerprint plots showing (a) all interactions, and those delineated into (b) H⋯H, (c) O⋯H/H⋯O, (d) C⋯C, (e) N⋯H/H⋯N, (f) C⋯H/H⋯C and (f) S⋯H/H⋯S interactions. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.

4. Database survey

A search in the Cambridge Structural Database (CSD, Version 6.00, updated April 2025; Groom et al., 2016 ) for the title compound reveals the five most closely related compounds, viz: (E)-2-(2-thienyl)-3-(3,4,5-trimethoxyphenyl)acrylonitrile [CSD refcode PEMBEP (I); Cobo et al., 2006a ], (E)-3-(4-bromophenyl)-2-(2-thienyl)acrylonitrile [PEMBIT (II); Cobo et al., 2006a], (E)-3-phenyl-2-(3-thienyl)acrylonitrile [PEMBOZ (III); Cobo et al., 2006a], (Z)-3-(4-methylphenyl)-2-(3-thienyl)acrylonitrile [QERPAF (IV); Cobo et al., 2006b ] and (Z)-2-phenyl-3-(2,2′:5′,2′′-terthiophen-3′-yl)acrylonitrile [UDUNAJ (V); Wagner et al., 2007 ].

Compounds (I), (III), (IV) and (V) crystallize in the mononlinic space group P2₁/c, whereas (II) crystallizes in the monoclinic space group P2₁/n.

Compound (I) contains no direction-specific intermolecular interactions. (II) exhibits orientational disorder of the thienyl fragment and the molecules are linked into simple C(5) chains by a single C—H⋯N hydrogen bond. In (III), the molecules are linked into sheets by a combination of one C—H⋯N hydrogen bond and one C—H⋯π(arene) hydrogen bond. In (I)–(III), the nitrile components exhibit quite long C—C bonds [1.443 (2)–1.446 (4) Å] and very short C—N bonds [1.143 (4)–1.146 (4) Å]. The remaining bond distances in (I)–(III) show no unusual features. In (IV), the shortest nonbonded intermolecular contacts between potential hydrogen-bond donors and acceptors are all too long to be structurally significant. In crystal structure (V), the van der Waals forces seem to determine the packing. Weak C—H⋯N and C—H⋯π interactions also might be of some importance.

While the contributions of the strong interactions are quite consistent, weak interactions vary slightly depending on the molecular conformation and the environment of the molecules.

5. Synthesis and crystallization

A solution of 3-oxo-3-(thiophen-2-yl)propanenitrile (0.5 g, 3.31 mmol) and 4-methoxybenzaldehyde (0.45 g, 3.31 mmol) in methanol (20 ml) was treated with a catalytic amount of N-methylpiperazine (1–2 drops). The reaction mixture was stirred vigorously at room temperature for 3 h, and the course of the reaction was monitored by thin-layer chromatography (TLC; Silufol UV-254 plates; hexane–ethyl acetate, 1:4 v/v). The resulting yellow crystals form directly; they were collected by filtration, washed with methanol and dried (m.p. 358 K; yield 91%).

¹H NMR (300 MHz, DMSO-d₆, ppm): 3.87 (s, 3H, CH₃O), 7.14–8.15 (m, 7H, 4CH_arom + 3CH_thienyl), 8.29 (s, 1H, CH=). ¹³C NMR (75 MHz, DMSO-d₆, ppm): 56.23 (CH₃O), 105.74 (=C_quat), 115.40 (2CH_arom), 118.14 (CN), 124.85 (C_thienyl), 129.45 (CH_thienyl), 134.13 (2CH_arom), 135.51 (CH_thienyl), 136.95 (CH_thienyl), 141.54 (C_arom), 155.21 (CH=), 164.03 (O—C_arom), 180.13 (C=O).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms were placed in calculated positions and were refined as riding atoms with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C). The methyl H atoms were allowed to rotate, but not to tip, to best fit the experimental electron density.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₁NO₂S
M_r	269.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.6250 (19), 13.0153 (18), 7.4161 (9)
β (°)	93.530 (4)
V (Å³)	1312.6 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.24
Crystal size (mm)	0.12 × 0.08 × 0.07

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2012 )
T_min, T_max	0.378, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	21480, 2678, 1704
R_int	0.095
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.139, 1.11
No. of reflections	2678
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.30
Computer programs: APEX2 (Bruker, 2012), SAINT (Bruker, 2012), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2594032

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S205698902601042X/nx2041sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698902601042X/nx2041Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S205698902601042X/nx2041Isup3.cml

checkCIF report

Computing details top

3-(4-Methoxyphenyl)-2-[(thiophen-2-yl)carbonyl]prop-2-enenitrile top

Crystal data top

C₁₅H₁₁NO₂S	F(000) = 560
M_r = 269.31	D_x = 1.363 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.6250 (19) Å	Cell parameters from 4702 reflections
b = 13.0153 (18) Å	θ = 3.0–22.2°
c = 7.4161 (9) Å	µ = 0.24 mm⁻¹
β = 93.530 (4)°	T = 293 K
V = 1312.6 (3) Å³	Block, yellow
Z = 4	0.12 × 0.08 × 0.07 mm

Data collection top

Bruker APEXII CCD diffractometer	1704 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.095
Absorption correction: multi-scan (SADABS; Bruker, 2012)	θ_max = 26.4°, θ_min = 3.0°
T_min = 0.378, T_max = 0.745	h = −16→17
21480 measured reflections	k = −16→16
2678 independent reflections	l = −8→9

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.075	H-atom parameters constrained
wR(F²) = 0.139	w = 1/[σ²(F_o²) + (0.0373P)² + 0.8766P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max < 0.001
2678 reflections	Δρ_max = 0.27 e Å⁻³
173 parameters	Δρ_min = −0.30 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
C1	0.1153 (3)	0.0523 (3)	0.3757 (4)	0.0547 (10)
H1	0.092826	−0.015035	0.364876	0.066*
C2	0.2084 (3)	0.0778 (3)	0.4318 (5)	0.0532 (9)
H2	0.256854	0.029829	0.464225	0.064*
C3	0.2242 (2)	0.1845 (2)	0.4359 (4)	0.0456 (9)
H3	0.284135	0.215146	0.470565	0.055*
C4	0.1405 (2)	0.2382 (2)	0.3825 (4)	0.0362 (7)
C5	0.1196 (2)	0.3491 (3)	0.3706 (4)	0.0398 (8)
C6	0.1994 (2)	0.4266 (2)	0.4097 (4)	0.0387 (8)
C7	0.2993 (2)	0.3988 (2)	0.3836 (5)	0.0485 (9)
C8	0.1746 (2)	0.5218 (2)	0.4635 (4)	0.0401 (8)
H8	0.107219	0.531495	0.469693	0.048*
C9	0.2328 (2)	0.6115 (2)	0.5133 (4)	0.0392 (8)
C10	0.1845 (2)	0.7056 (3)	0.5236 (4)	0.0453 (8)
H10	0.116438	0.707623	0.505124	0.054*
C11	0.2345 (2)	0.7946 (3)	0.5600 (4)	0.0487 (9)
H11	0.200412	0.856348	0.564421	0.058*
C12	0.3361 (2)	0.7934 (3)	0.5904 (4)	0.0439 (8)
C13	0.3847 (2)	0.7009 (3)	0.5890 (4)	0.0497 (9)
H13	0.452436	0.699000	0.613981	0.060*
C14	0.3346 (2)	0.6118 (3)	0.5512 (4)	0.0482 (9)
H14	0.368904	0.549987	0.550763	0.058*
C15	0.4836 (3)	0.8892 (3)	0.6548 (6)	0.0774 (12)
H15A	0.514909	0.862440	0.552324	0.116*
H15B	0.501480	0.848084	0.759237	0.116*
H15C	0.504330	0.958798	0.676470	0.116*
N1	0.3776 (2)	0.3766 (2)	0.3524 (5)	0.0784 (11)
O1	0.03542 (15)	0.37924 (17)	0.3351 (3)	0.0563 (6)
O2	0.37932 (16)	0.88645 (17)	0.6199 (3)	0.0591 (7)
S1	0.04432 (6)	0.15631 (7)	0.32754 (12)	0.0535 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.068 (3)	0.039 (2)	0.057 (2)	−0.0065 (18)	0.0052 (19)	−0.0029 (17)
C2	0.050 (2)	0.046 (2)	0.064 (2)	0.0061 (17)	0.0009 (18)	0.0068 (18)
C3	0.040 (2)	0.036 (2)	0.060 (2)	0.0000 (15)	−0.0060 (16)	0.0078 (16)
C4	0.0377 (17)	0.0354 (19)	0.0354 (18)	0.0000 (15)	0.0020 (13)	−0.0007 (14)
C5	0.0283 (18)	0.052 (2)	0.0393 (19)	0.0012 (16)	0.0020 (14)	0.0007 (16)
C6	0.0305 (18)	0.040 (2)	0.0452 (19)	0.0078 (14)	−0.0014 (14)	0.0049 (15)
C7	0.035 (2)	0.036 (2)	0.074 (3)	0.0019 (16)	0.0008 (17)	−0.0039 (17)
C8	0.0286 (17)	0.044 (2)	0.047 (2)	0.0093 (15)	0.0011 (14)	0.0040 (16)
C9	0.0341 (18)	0.040 (2)	0.0431 (19)	0.0061 (15)	0.0011 (14)	0.0046 (15)
C10	0.0322 (18)	0.045 (2)	0.059 (2)	0.0077 (16)	0.0031 (15)	0.0004 (17)
C11	0.045 (2)	0.035 (2)	0.066 (2)	0.0147 (16)	0.0032 (17)	0.0017 (17)
C12	0.045 (2)	0.041 (2)	0.046 (2)	−0.0035 (17)	0.0040 (16)	−0.0012 (16)
C13	0.0329 (19)	0.050 (2)	0.066 (2)	0.0055 (17)	−0.0048 (16)	−0.0030 (18)
C14	0.038 (2)	0.040 (2)	0.065 (2)	0.0108 (16)	−0.0065 (16)	−0.0013 (17)
C15	0.054 (3)	0.073 (3)	0.105 (3)	−0.019 (2)	0.000 (2)	−0.005 (2)
N1	0.0395 (18)	0.055 (2)	0.141 (3)	0.0077 (16)	0.0098 (19)	−0.006 (2)
O1	0.0294 (13)	0.0551 (15)	0.0832 (17)	0.0061 (11)	−0.0054 (11)	0.0037 (13)
O2	0.0520 (16)	0.0452 (15)	0.0789 (18)	−0.0051 (12)	−0.0061 (13)	−0.0003 (12)
S1	0.0425 (5)	0.0562 (6)	0.0608 (6)	−0.0059 (4)	−0.0039 (4)	−0.0043 (5)

Geometric parameters (Å, º) top

C1—C2	1.352 (4)	C9—C10	1.394 (4)
C1—S1	1.689 (4)	C9—C14	1.398 (4)
C1—H1	0.9300	C10—C11	1.361 (4)
C2—C3	1.405 (5)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.389 (4)
C3—C4	1.375 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—O2	1.359 (4)
C4—C5	1.473 (4)	C12—C13	1.374 (4)
C4—S1	1.718 (3)	C13—C14	1.367 (4)
C5—O1	1.226 (3)	C13—H13	0.9300
C5—C6	1.498 (4)	C14—H14	0.9300
C6—C8	1.351 (4)	C15—O2	1.428 (4)
C6—C7	1.433 (4)	C15—H15A	0.9600
C7—N1	1.142 (4)	C15—H15B	0.9600
C8—C9	1.447 (4)	C15—H15C	0.9600
C8—H8	0.9300

C2—C1—S1	112.5 (3)	C14—C9—C8	125.1 (3)
C2—C1—H1	123.8	C11—C10—C9	121.8 (3)
S1—C1—H1	123.8	C11—C10—H10	119.1
C1—C2—C3	112.9 (3)	C9—C10—H10	119.1
C1—C2—H2	123.5	C10—C11—C12	120.2 (3)
C3—C2—H2	123.5	C10—C11—H11	119.9
C4—C3—C2	111.8 (3)	C12—C11—H11	119.9
C4—C3—H3	124.1	O2—C12—C13	125.3 (3)
C2—C3—H3	124.1	O2—C12—C11	115.7 (3)
C3—C4—C5	131.9 (3)	C13—C12—C11	119.0 (3)
C3—C4—S1	111.1 (2)	C14—C13—C12	120.7 (3)
C5—C4—S1	116.9 (2)	C14—C13—H13	119.7
O1—C5—C4	120.1 (3)	C12—C13—H13	119.7
O1—C5—C6	119.0 (3)	C13—C14—C9	121.3 (3)
C4—C5—C6	120.9 (3)	C13—C14—H14	119.3
C8—C6—C7	121.9 (3)	C9—C14—H14	119.3
C8—C6—C5	118.8 (3)	O2—C15—H15A	109.5
C7—C6—C5	119.2 (3)	O2—C15—H15B	109.5
N1—C7—C6	176.1 (4)	H15A—C15—H15B	109.5
C6—C8—C9	132.2 (3)	O2—C15—H15C	109.5
C6—C8—H8	113.9	H15A—C15—H15C	109.5
C9—C8—H8	113.9	H15B—C15—H15C	109.5
C10—C9—C14	116.9 (3)	C12—O2—C15	117.9 (3)
C10—C9—C8	118.0 (3)	C1—S1—C4	91.64 (16)

S1—C1—C2—C3	−0.3 (4)	C14—C9—C10—C11	3.2 (5)
C1—C2—C3—C4	0.3 (4)	C8—C9—C10—C11	−176.4 (3)
C2—C3—C4—C5	177.6 (3)	C9—C10—C11—C12	−0.8 (5)
C2—C3—C4—S1	−0.2 (3)	C10—C11—C12—O2	178.0 (3)
C3—C4—C5—O1	−172.8 (3)	C10—C11—C12—C13	−2.1 (5)
S1—C4—C5—O1	4.9 (4)	O2—C12—C13—C14	−177.5 (3)
C3—C4—C5—C6	4.4 (5)	C11—C12—C13—C14	2.5 (5)
S1—C4—C5—C6	−177.9 (2)	C12—C13—C14—C9	−0.1 (5)
O1—C5—C6—C8	21.7 (4)	C10—C9—C14—C13	−2.7 (5)
C4—C5—C6—C8	−155.6 (3)	C8—C9—C14—C13	176.8 (3)
O1—C5—C6—C7	−156.4 (3)	C13—C12—O2—C15	−0.9 (5)
C4—C5—C6—C7	26.4 (4)	C11—C12—O2—C15	179.0 (3)
C7—C6—C8—C9	−3.1 (5)	C2—C1—S1—C4	0.1 (3)
C5—C6—C8—C9	178.9 (3)	C3—C4—S1—C1	0.1 (2)
C6—C8—C9—C10	165.7 (3)	C5—C4—S1—C1	−178.1 (2)
C6—C8—C9—C14	−13.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1	0.93	2.40	2.779 (3)	104
C13—H13···N1ⁱ	0.93	2.51	3.394 (4)	158

Symmetry code: (i) −x+1, −y+1, −z+1.

Summary of short interatomic contacts (Å) top

Contact	Distance	Symmetry operation
H10···O1	2.70	-x, 1-y, 1-z
C1···C8	3.35	x, 1/2-y, -1/2+z
O1···H1	2.61	-x, 1/2+y, 1/2-z
H11···H2	2.51	x, 1+y, z
H15B···C13	3.07	x, 3/2-y, 1/2+z
H13···N1	2.51	1-x, 1-y, 1-z

Acknowledgements

Funding for this research was provided by: Baku State University. The contributions of the authors are as follows. Conceptualization, EZH and IGM; methodology, FNN and ASS; investigation, JMA, MA and HAH; writing (original draft), MA and EZH; writing (review and editing of the manuscript), MA and ASS; visualization, MA, MMK and IGM; funding acquisition, EZH, HAH and FNN; resources, JMA, MA, JMA and MMK; supervision, EZH and ASS.

References

Abdullayeva, F. M., Maharramov, A. M., Huseyinov, E. Z., Pashayeva, Z. N. & Safarova, A. S. (2026). New Mater. Compd Appl. 10, 138–150. Google Scholar
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
Asgarova, A. R., Khalilov, A. N., Brito, I., Maharramov, A. M., Shikhaliyev, N. G., Cisterna, J., Cárdenas, A., Gurbanov, A. V., Zubkov, F. I. & Mahmudov, K. T. (2019). Acta Cryst. C75, 342–347. Web of Science CSD CrossRef IUCr Journals Google Scholar
Askerov, R. K., Maharramov, A. M., Khalilov, A. N., Akkurt, M., Akobirshoeva, A. A., Osmanov, V. K. & Borisov, A. V. (2020). Acta Cryst. E76, 1007–1011. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2012). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cobo, D., Cobo, J., Low, J. N. & Glidewell, C. (2006b). Acta Cryst. E62, o5179–o5180. CrossRef IUCr Journals Google Scholar
Cobo, D., Quiroga, J., de la Torre, J. M., Cobo, J., Low, J. N. & Glidewell, C. (2006a). Acta Cryst. C62, o550–o553. CrossRef IUCr Journals 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
Karimli, E. G., Khrustalev, V. N., Akkurt, M., Khalilov, A. N., Bhattarai, A., Aleskerova, A. N. & Mamedov, İ. G. (2023). Acta Cryst. E79, 777–781. Web of Science CrossRef IUCr Journals Google Scholar
Khalilov, A. N., Abdelhamid, A. A., Gurbanov, A. V. & Ng, S. W. (2011). Acta Cryst. E67, o1146. Web of Science CSD CrossRef IUCr Journals Google Scholar
Khalilov, A. N., Khrustalev, V. N., Aleksandrova, L. V., Akkurt, M., Rzayev, R. M., Bhattarai, A. & Mamedov, İ. G. (2023). Acta Cryst. E79, 436–440. Web of Science CrossRef IUCr Journals Google Scholar
Mamedov, I. & Khalilov, A. (2025). Baghdad Sci. J. 22, 2239–2245. Web of Science CrossRef Google Scholar
Naghiyev, F. N., Grishina, M. M., Khrustalev, V. N., Khalilov, A. N., Akkurt, M., Akobirshoeva, A. A. & Mamedov, İ. G. (2021). Acta Cryst. E77, 195–199. Web of Science CSD CrossRef IUCr Journals Google Scholar
Naghiyev, F. N., Khrustalev, V. N., Akkurt, M., Asadov, K. A., Bhattarai, A., Khalilov, A. N. & Mamedov, İ. G. (2024). Acta Cryst. E80, 446–451. Web of Science CSD CrossRef IUCr Journals Google Scholar
Naghiyev, F. N., Khrustalev, V. N., Akkurt, M., Khalilov, A. N., Bhattarai, A., Kerimli, F. S. & Mamedov, İ. G. (2023). Acta Cryst. E79, 494–498. Web of Science CSD CrossRef IUCr Journals Google Scholar
Naghiyev, F. N., Khrustalev, V. N., Dobrokhotova, E. V., Akkurt, M., Khalilov, A. N., Bhattarai, A. & Mamedov, İ. G. (2022). Acta Cryst. E78, 568–573. Web of Science CSD CrossRef 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
Shikhaliyev, N. G., Cisterna, J., Gajar, A. M., Niyazova, A. A., Khalilov, A. N., Khrustalev, V. N., Belay, A. N. & Maharramov, A. M. (2025). Acta Cryst. E81, 662–666. Web of Science CrossRef IUCr Journals Google Scholar
Spackman, P. R., Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Jayatilaka, D. & Spackman, M. A. (2021). J. Appl. Cryst. 54, 1006–1011. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Tüzün, B., Agbektas, T., Naghiyev, F. N., Tas, A., Zontul, C., Ozum, U., Khalilov, A. N., Silig, Y., Çakmak, N. K. & Mamedov, I. G. (2025). Monatsh. Chem. 156, 667–688. Google Scholar
Wagner, P., Officer, D. L. & Kubicki, M. (2007). Acta Cryst. E63, o3054–o3055. CrossRef IUCr Journals Google Scholar

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