Crystal structure and Hirshfeld surface analysis of (E)-1-(2,4-di­methyl­furan-3-yl)-3-phenyl­prop-2-en-1-one

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

doi:10.1107/S2056989023006084

research communications

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ISSN: 2056-9890

Volume 79| Part 8| August 2023| Pages 736-740

https://doi.org/10.1107/S2056989023006084

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Crystal structure and Hirshfeld surface analysis of (E)-1-(2,4-dimethylfuran-3-yl)-3-phenylprop-2-en-1-one

Ali N. Khalilov,^a,^b Victor N. Khrustalev,^c,^d Aida I. Samigullina,^d 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 L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 6 July 2023; accepted 10 July 2023; online 14 July 2023)

The title compound, C₁₅H₁₄O₂, adopts an E configuration about the C=C double bond. The furan ring is inclined to the phenyl ring by 12.03 (9)°. In the crystal, pairs of molecules are linked by C—H⋯O hydrogen bonds, forming dimers with R²₂(14) ring motifs. The molecules are connected via C—H⋯π interactions, forming a three dimensional network. No π–π interactions are observed.

Keywords: crystal structure; 2,4-dimethylfuran; chalcones; hydrogen bond; C—H⋯π interactions; Hirshfeld surface analysis.

CCDC reference: 2280559

1. Chemical context

Various C—C, C—N, C—S and C—O bond-formation reactions are keystones in organic synthesis. The application of such reactions has been expanded considerably, extending these approaches in different branches of chemistry, including green, medicinal, pharmaceutical and natural products chemistry, material science, supramolecular chemistry (Asadov et al., 2003 ; Çelik et al., 2023 ; Chalkha et al., 2023 ; Gurbanov et al., 2020 ; Zubkov et al., 2018 ). α,β-Unsaturated ketones containing aryl–aryl or aryl–alkyl groups at both ends are known as chalcones or enones. There have been several important examples of enone derivatives used as target products and also as synthetic intermediates. Many natural compounds containing enone moieties, such as cyanthiwigin U, (+)-cepharamine, phorbol and grandisine G, have been the object of a total synthesis (Cuthbertson & Taylor, 2013 ; Kawamura et al., 2016 ). These compounds have been obtained by many solvent-assisted or solvent-free methods. The enone moiety is a widespread structural motif of various synthetic biologically active compounds, possessing enzyme inhibitory, anticancer and antimicrobial activity (Poustforoosh et al., 2022 ; Tapera et al., 2022 ; Sarkı et al., 2023 ).

In a continuation of our investigations in heterocyclic systems exhibiting biological activity and in the framework of ongoing structural studies (Maharramov et al., 2021 , 2022 ), we report herein the crystal structure and Hirshfeld surface analysis of the title compound, (E)-1-(2,4-dimethylfuran-3-yl)-3-phenylprop-2-en-1-one.

2. Structural commentary

As seen as Fig. 1, the title compound adopts an E configuration about the C=C double bond. The whole molecule is nearly planar. The furan ring (O1/C2–C5) is inclined to the phenyl ring (C9–C14) by 12.03 (9)°. The torsion angles are C2—C3—C6—O2 = 14.5 (2), C2—C3—C6—C7 = −164.79 (15), C3—C6—C7—C8 = −173.80 (15), C6—C7—C8—C9 = 179.30 (15) and C7—C8—C9—C10 = 172.52 (16)°. The geometrical parameter values of the the title compound are in agreement with those reported for similar compounds in the Database survey section.

Figure 1
The molecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at the 50% probability level.

3. Supramolecular features and Hirshfeld surface analysis

In the crystal, pairs of molecules are linked by C—H⋯O hydrogen bonds, forming dimers with $[R_{2}^{2}]$ (14) ring motifs (Bernstein et al., 1995 ; Table 1; Figs. 2 and 3). The molecules are connected via C—H⋯π interactions, forming a three-dimensional network (Table 1; Fig. 4). No π–π interactions are observed.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the furan (O1/C2–C5) and phenyl (C9–C14) rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2ⁱ	0.95	2.52	3.413 (2)	157
C12—H12⋯Cg1ⁱⁱ	0.95	2.91	3.7339 (19)	146
C15—H15B⋯Cg2ⁱⁱⁱ	0.98	2.85	3.6366 (19)	137
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) $[-x+{\script{3\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
View of the C—H⋯O hydrogen bonds and C—H⋯π interactions of the title compound down the a axis. Only the H atoms involved in these interactions have been included.

Figure 3
View of the C—H⋯O hydrogen bonds and C—H⋯π interactions of the title compound down the b axis. Only the H atoms involved in these interactions have been included.

Figure 4
View of the C—H⋯O hydrogen bonds and C—H⋯π interactions of the title compound down the c axis. Only the H atoms involved in these interactions have been included.

CrystalExplorer17.5 (Spackman et al., 2021 ) was used to compute Hirshfeld surfaces of the title molecule and two-dimensional fingerprints. The d_norm mappings for the title compound were performed in the range −0.1518 (red) to +1.1567 (blue) a.u. On the d_norm surfaces, bright-red spots indicate the locations of the C—H⋯O interactions and O⋯C/C⋯O contacts (Tables 1 and 2; Fig. 5a,b).

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

H1B⋯H8	2.57	−1 + x, y, z
H1C⋯H13	2.52	$[{3\over 2}]$ − x, 1 − y, $[{1\over 2}]$ + z
H1B⋯H8	2.47	− $[{1\over 2}]$ + x, $[{3\over 2}]$ − y, 1 − z
H1A⋯H10	2.39	− $[{3\over 2}]$ + x, $[{3\over 2}]$ − y, 1 − z
C12⋯H5	2.94	1 − x, $[{1\over 2}]$ + y, $[{1\over 2}]$ − z
H13⋯H1A	2.49	$[{1\over 2}]$ − x, 1 − y, − $[{1\over 2}]$ + z
C15⋯H11	3.05	2 − x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z

Figure 5
(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 −0.1518 to +1.1567 a.u.

The most important interatomic contact is H⋯H (51.1%; Fig. 6b) as it makes the highest contribution to the crystal packing. The C⋯H/H⋯C (Fig. 6c; 25.3%), O⋯H/H⋯O (Fig. 6d; 15.9%), C⋯C (5.1%) and O⋯C/C⋯O (2.5%) contacts have little directional influence on the molecular packing.

Figure 6
The two-dimensional fingerprint plots of the title compound, showing (a) all interactions, and delineated into (b) H⋯H, (c) C⋯H/H⋯C and (d) O⋯H/H⋯O 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 5.43, last update November 2022; Groom et al., 2016 ) for the `1-(furan-3-yl)-3-phenylprop-2-en-1-one' skeleton of the title compound yielded one hit, 1-(3-furyl)-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-one (CSD refcode KUDNAA; Bąkowicz et al., 2015 ). When the positions of the furan and phenyl rings are switched, 1-(3-chlorophenyl)-3-(3-furyl)prop-2-en-1-one (NUQFOW; Zingales et al. 2015 ), (E)-3-(2-furyl)-1-phenylprop-2-en-1-one (NOTCUW01; Vázquez-Vuelvas et al. 2015 ) are the most similar structures.

In KUDNAA, molecules are linked by intermolecular C—H⋯O interactions, forming zigzag chains with C(5) motifs along the b-axis direction. In addition, molecules are connected by face-to-face π–π stacking interactions [centroid–centroid distances = 3.926 (3) and 3.925 (2) Å] between the opposing benzene and furan rings of the molecules along the c-axis direction. In NUQFOW, the molecule exhibits a non-planar geometry, the furan ring being inclined to the benzene ring by 50.52 (16)°. In the crystal of NUQFOW, molecules stack along the a-axis; however, there are no significant intermolecular interactions present. In NOTCUW01, the molecule also adopts an E configuration about the C=C double bond and the furan and phenyl rings are inclined to one another by 24.07 (7)°. In the crystal of NOTCUW01, molecules are connected by weak C—H⋯O hydrogen bonds and C—H⋯π interactions, forming ribbons extending along the c-axis direction.

5. Synthesis and crystallization

To a solution of 1-(2,4-dimethylfuran-3-yl)ethan-1-one (2 g, 14.5 mmol) in ethanol (10 mL), were added 10 mL of aqueous solution of sodium hydroxide (0.65 g, 16.3 mmol) and the mixture was stirred at room temperature for 2 h. Then benzaldehyde (1.73 g, 16.3 mmol) was added to the vigorously stirred reaction mixture and it was left overnight. The precipitated crystals were separated by filtration and recrystallized from an ethanol/water (1:1) solution (yield 90%; m.p. 349–350 K).

¹H NMR (300 MHz, DMSO-d₆, ppm): 2.1 (s, 3H, CH₃); 2.5 (s, 3H, CH₃); 7.2 (d, 1H, =CH, ³J_H–H = 15.8 Hz); 7.3 (s, 1H, fur.), 7.4 (m, 3H, arom.), 7.5 (d, 1H, =CH, ³J_H–H = 15.8 Hz); 7.8 (m, 2H, arom.). ¹³C NMR (75 MHz, DMSO-d₆, ppm): 10.3 (CH₃), 15.0 (CH₃), 120.4 (C_quat.), 122.9 (C_quat.), 126.3 (=CH), 128.9 (CH, arom.), 129.4 (CH, arom.), 130.9 (CH, arom.), 134.8 (C_quat.), 139.0 (CH, furan), 142.8 (=CH), 158.2 (C_quat.), 187.7 (CO).

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 and 0.98 Å, and with U_iso(H) = 1.2 or 1.5U_eq(C).

Table 3
Experimental details

Crystal data
Chemical formula	C₁₅H₁₄O₂
M_r	226.26
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	5.84787 (5), 12.18109 (9), 16.24568 (15)
V (Å³)	1157.24 (2)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.68
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	XtaLAB Synergy, Dualflex, HyPix
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.579, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12000, 2410, 2382
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.081, 1.06
No. of reflections	2410
No. of parameters	157
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.24
Absolute structure	Flack x determined using 940 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.16 (7)
Computer programs: CrysAlis PRO (Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT2014/5 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2280559

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989023006084/vm2287sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023006084/vm2287Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989023006084/vm2287Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO 1.171.41.117a (Rigaku OD, 2021); cell refinement: CrysAlis PRO 1.171.41.117a (Rigaku OD, 2021); data reduction: CrysAlis PRO 1.171.41.117a (Rigaku OD, 2021); 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).

(E)-1-(2,4-Dimethylfuran-3-yl)-3-phenylprop-2-en-1-one top

Crystal data top

C₁₅H₁₄O₂	D_x = 1.299 Mg m⁻³
M_r = 226.26	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 10780 reflections
a = 5.84787 (5) Å	θ = 4.5–77.7°
b = 12.18109 (9) Å	µ = 0.68 mm⁻¹
c = 16.24568 (15) Å	T = 100 K
V = 1157.24 (2) Å³	Prism, colourless
Z = 4	0.24 × 0.20 × 0.18 mm
F(000) = 480

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	2382 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube	R_int = 0.031
φ and ω scans	θ_max = 77.8°, θ_min = 4.5°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021)	h = −7→6
T_min = 0.579, T_max = 1.000	k = −15→15
12000 measured reflections	l = −20→20
2410 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.030	w = 1/[σ²(F_o²) + (0.0426P)² + 0.3199P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.081	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.18 e Å⁻³
2410 reflections	Δρ_min = −0.24 e Å⁻³
157 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0046 (4)
Primary atom site location: difference Fourier map	Absolute structure: Flack x determined using 940 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.16 (7)

Special details top

Experimental. CrysAlisPro 1.171.41.117a (Rigaku OD, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	−0.1250 (2)	0.42159 (10)	0.52334 (8)	0.0225 (3)
O2	0.4218 (2)	0.63977 (10)	0.51486 (7)	0.0208 (3)
C1	−0.0327 (3)	0.59606 (14)	0.58548 (11)	0.0211 (4)
H1A	−0.1936	0.5903	0.6018	0.032*
H1B	−0.0064	0.6672	0.5590	0.032*
H1C	0.0647	0.5898	0.6343	0.032*
C2	0.0234 (3)	0.50662 (13)	0.52698 (10)	0.0174 (3)
C3	0.1991 (3)	0.49066 (13)	0.47138 (10)	0.0162 (3)
C4	0.1518 (3)	0.38801 (13)	0.43028 (10)	0.0183 (4)
C5	−0.0431 (3)	0.34981 (13)	0.46379 (11)	0.0197 (3)
H5	−0.1150	0.2828	0.4488	0.024*
C6	0.3897 (3)	0.56901 (13)	0.46209 (10)	0.0165 (3)
C7	0.5382 (3)	0.56193 (14)	0.38864 (10)	0.0184 (3)
H7	0.5012	0.5122	0.3456	0.022*
C8	0.7247 (3)	0.62533 (13)	0.38247 (10)	0.0169 (3)
H8	0.7528	0.6742	0.4269	0.020*
C9	0.8896 (3)	0.62758 (13)	0.31489 (10)	0.0162 (3)
C10	1.0585 (3)	0.70888 (13)	0.31532 (11)	0.0193 (3)
H10	1.0611	0.7615	0.3584	0.023*
C11	1.2225 (3)	0.71374 (14)	0.25365 (11)	0.0217 (4)
H11	1.3360	0.7695	0.2547	0.026*
C12	1.2207 (3)	0.63690 (14)	0.19019 (11)	0.0206 (4)
H12	1.3331	0.6400	0.1480	0.025*
C13	1.0538 (3)	0.55571 (14)	0.18888 (11)	0.0214 (4)
H13	1.0518	0.5033	0.1456	0.026*
C14	0.8901 (3)	0.55079 (14)	0.25044 (11)	0.0207 (3)
H14	0.7771	0.4948	0.2490	0.025*
C15	0.2820 (3)	0.32838 (14)	0.36480 (11)	0.0222 (4)
H15A	0.2637	0.3667	0.3122	0.033*
H15B	0.2231	0.2534	0.3598	0.033*
H15C	0.4444	0.3260	0.3796	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0189 (6)	0.0244 (6)	0.0242 (6)	−0.0017 (5)	0.0021 (5)	0.0025 (5)
O2	0.0195 (6)	0.0223 (6)	0.0207 (6)	−0.0032 (5)	0.0029 (5)	−0.0048 (5)
C1	0.0186 (7)	0.0235 (8)	0.0211 (8)	0.0027 (7)	0.0039 (7)	0.0001 (6)
C2	0.0161 (7)	0.0175 (7)	0.0187 (8)	0.0009 (6)	−0.0019 (6)	0.0034 (6)
C3	0.0155 (7)	0.0171 (7)	0.0161 (7)	0.0005 (6)	−0.0013 (6)	0.0017 (6)
C4	0.0190 (8)	0.0175 (8)	0.0184 (7)	0.0015 (6)	−0.0016 (6)	0.0009 (6)
C5	0.0190 (7)	0.0160 (7)	0.0241 (8)	−0.0030 (6)	−0.0008 (7)	−0.0005 (6)
C6	0.0155 (7)	0.0167 (7)	0.0172 (7)	0.0020 (6)	−0.0014 (6)	0.0011 (6)
C7	0.0189 (7)	0.0185 (7)	0.0177 (7)	−0.0006 (6)	0.0009 (6)	−0.0025 (6)
C8	0.0181 (7)	0.0154 (7)	0.0172 (7)	0.0021 (6)	−0.0007 (6)	−0.0011 (6)
C9	0.0155 (7)	0.0170 (7)	0.0160 (7)	0.0009 (6)	0.0002 (6)	0.0010 (6)
C10	0.0192 (8)	0.0182 (7)	0.0204 (8)	−0.0017 (7)	0.0003 (7)	−0.0035 (6)
C11	0.0192 (8)	0.0208 (8)	0.0250 (8)	−0.0056 (7)	0.0037 (7)	−0.0011 (7)
C12	0.0193 (8)	0.0224 (8)	0.0200 (8)	0.0008 (7)	0.0044 (7)	0.0006 (7)
C13	0.0225 (8)	0.0218 (8)	0.0199 (8)	−0.0018 (7)	0.0024 (7)	−0.0047 (7)
C14	0.0193 (7)	0.0201 (8)	0.0226 (8)	−0.0055 (7)	0.0023 (7)	−0.0042 (6)
C15	0.0222 (8)	0.0187 (8)	0.0258 (9)	−0.0009 (7)	0.0014 (7)	−0.0060 (7)

Geometric parameters (Å, º) top

O1—C2	1.352 (2)	C8—C9	1.461 (2)
O1—C5	1.389 (2)	C8—H8	0.9500
O2—C6	1.230 (2)	C9—C10	1.399 (2)
C1—C2	1.482 (2)	C9—C14	1.404 (2)
C1—H1A	0.9800	C10—C11	1.388 (2)
C1—H1B	0.9800	C10—H10	0.9500
C1—H1C	0.9800	C11—C12	1.392 (2)
C2—C3	1.382 (2)	C11—H11	0.9500
C3—C4	1.444 (2)	C12—C13	1.390 (2)
C3—C6	1.475 (2)	C12—H12	0.9500
C4—C5	1.346 (2)	C13—C14	1.385 (2)
C4—C15	1.496 (2)	C13—H13	0.9500
C5—H5	0.9500	C14—H14	0.9500
C6—C7	1.478 (2)	C15—H15A	0.9800
C7—C8	1.340 (2)	C15—H15B	0.9800
C7—H7	0.9500	C15—H15C	0.9800

C2—O1—C5	106.96 (13)	C7—C8—H8	116.4
C2—C1—H1A	109.5	C9—C8—H8	116.4
C2—C1—H1B	109.5	C10—C9—C14	118.27 (15)
H1A—C1—H1B	109.5	C10—C9—C8	118.39 (14)
C2—C1—H1C	109.5	C14—C9—C8	123.32 (15)
H1A—C1—H1C	109.5	C11—C10—C9	120.97 (15)
H1B—C1—H1C	109.5	C11—C10—H10	119.5
O1—C2—C3	109.92 (14)	C9—C10—H10	119.5
O1—C2—C1	116.68 (14)	C10—C11—C12	120.04 (16)
C3—C2—C1	133.39 (16)	C10—C11—H11	120.0
C2—C3—C4	106.33 (14)	C12—C11—H11	120.0
C2—C3—C6	122.53 (15)	C13—C12—C11	119.66 (16)
C4—C3—C6	131.14 (15)	C13—C12—H12	120.2
C5—C4—C3	105.95 (15)	C11—C12—H12	120.2
C5—C4—C15	123.41 (16)	C14—C13—C12	120.33 (15)
C3—C4—C15	130.63 (15)	C14—C13—H13	119.8
C4—C5—O1	110.84 (14)	C12—C13—H13	119.8
C4—C5—H5	124.6	C13—C14—C9	120.75 (16)
O1—C5—H5	124.6	C13—C14—H14	119.6
O2—C6—C3	119.83 (15)	C9—C14—H14	119.6
O2—C6—C7	120.92 (15)	C4—C15—H15A	109.5
C3—C6—C7	119.25 (14)	C4—C15—H15B	109.5
C8—C7—C6	120.31 (15)	H15A—C15—H15B	109.5
C8—C7—H7	119.8	C4—C15—H15C	109.5
C6—C7—H7	119.8	H15A—C15—H15C	109.5
C7—C8—C9	127.15 (15)	H15B—C15—H15C	109.5

C5—O1—C2—C3	−0.31 (17)	C2—C3—C6—C7	−164.79 (15)
C5—O1—C2—C1	178.43 (14)	C4—C3—C6—C7	15.8 (3)
O1—C2—C3—C4	0.56 (18)	O2—C6—C7—C8	6.9 (2)
C1—C2—C3—C4	−177.90 (17)	C3—C6—C7—C8	−173.80 (15)
O1—C2—C3—C6	−179.00 (14)	C6—C7—C8—C9	179.30 (15)
C1—C2—C3—C6	2.5 (3)	C7—C8—C9—C10	172.52 (16)
C2—C3—C4—C5	−0.59 (18)	C7—C8—C9—C14	−8.9 (3)
C6—C3—C4—C5	178.92 (17)	C14—C9—C10—C11	0.1 (3)
C2—C3—C4—C15	−179.55 (17)	C8—C9—C10—C11	178.70 (16)
C6—C3—C4—C15	0.0 (3)	C9—C10—C11—C12	−0.1 (3)
C3—C4—C5—O1	0.42 (18)	C10—C11—C12—C13	0.2 (3)
C15—C4—C5—O1	179.47 (15)	C11—C12—C13—C14	−0.2 (3)
C2—O1—C5—C4	−0.08 (18)	C12—C13—C14—C9	0.2 (3)
C2—C3—C6—O2	14.5 (2)	C10—C9—C14—C13	−0.1 (3)
C4—C3—C6—O2	−164.92 (16)	C8—C9—C14—C13	−178.66 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the furan (O1/C2–C5) and phenyl (C9–C14) rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2	0.95	2.44	2.792 (2)	102
C10—H10···O2ⁱ	0.95	2.52	3.413 (2)	157
C12—H12···Cg1ⁱⁱ	0.95	2.91	3.7339 (19)	146
C15—H15B···Cg2ⁱⁱⁱ	0.98	2.85	3.6366 (19)	137

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

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

H1B···H8	2.57	-1 + x, y, z
H1C···H13	2.52	3/2 - x, 1 - y, 1/2 + z
H1B···H8	2.47	-1/2 + x, 3/2 - y, 1 - z
H1A···H10	2.39	-3/2 + x, 3/2 - y, 1 - z
C12···H5	2.94	1 - x, 1/2 + y, 1/2 - z
H13···H1A	2.49	1/2 - x, 1 - y, -1/2 + z
C15···H11	3.05	2 - x, -1/2 + y, 1/2 - z

Acknowledgements

Authors' contributions are as follows. Conceptualization, ANK and IGM; methodology, ANK, FNN and IGM; investigation, ANK, MA and AİS; 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 and RMR; supervision, ANK and MA.

Funding information

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

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