(E)-1-(2-Hy­droxy­phen­yl)-3-(3-meth­oxy­phen­yl)prop-2-en-1-one

Naghiyev, F.N.; Hökelek, T.; Khrustalev, V.N.; Zueva, A.Y.; Asadov, K.A.; Belay, A.N.; Mamedov, I.G.

doi:10.1107/S2414314625001828

organic compounds

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ISSN: 2414-3146

Volume 10| Part 3| March 2025| x250182

https://doi.org/10.1107/S2414314625001828

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(E)-1-(2-Hydroxyphenyl)-3-(3-methoxyphenyl)prop-2-en-1-one

Farid N. Naghiyev,^a Tuncer Hökelek,^b Victor N. Khrustalev,^c,^d Anna Yu Zueva,^c Khammed A. Asadov,^a Alebel N. Belay ^e ^* and Ibrahim G. Mamedov ^a

^aDepartment of Chemistry, Baku State University, Z. Khalilov Str. 23, Az 1148 Baku, Azerbaijan, ^bHacettepe University, Department of Physics, 06800 Beytepe-Ankara, Türkiye, ^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, and ^eDepartment of Chemistry, Bahir Dar University, PO Box 79, Bahir Dar, Ethiopia
^*Correspondence e-mail: alebel.nibret@bdu.edu.et

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 18 February 2025; accepted 26 February 2025; online 4 March 2025)

In the title compound, C₁₆H₁₄O₃, the phenyl rings are oriented at a dihedral angle of 3.82 (3)° and an intramolecular O—H⋯O hydrogen bond closes an S(6) ring. In the crystal, weak C—H⋯O and C—H⋯π hydrogen bonds and aromatic π–π stacking occurs. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (48.2%), H⋯O/O⋯H (20.0%), H⋯C/C⋯H (16.5%) and C⋯C (12.7%) interactions.

Keywords: crystal structure; carboxylate; hydrogen bond.

CCDC reference: 2427472

Structure description

Chalcones are open-chain flavonoids, widely recognized as versatile building blocks in organic synthesis, owing to their α,β-unsaturated carbonyl system that facilitates the formation of diverse chemical frameworks (e.g., Khalilov et al., 2022 ). As part of our ongoing studies in this area, we now report the synthesis and structure of the title compound, C₁₆H₁₄O₃, (I).

The phenyl rings (C2–C7 and C10–C15) are oriented at a dihedral angle of 3.82 (3)° (Fig. 1) and the C2—C1—C8—C9 and C1—C8—C9—C10 torsion angles are −177.00 (9) and −178.67 (9)°, respectively. A short (and presumably strong) intramolecular O2—H2⋯O1 hydrogen bond occurs (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.96 (2)	1.61 (2)	2.5156 (10)	154.9 (19)
C14—H14⋯O2ⁱ	0.95	2.49	3.4220 (13)	167
C16—H16C⋯Cg1ⁱⁱ	0.98	2.71	3.5097 (13)	140
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Figure 1
The molecular structure of (I) showing 50% probability ellipsoids. The intramolecular O—H⋯O hydrogen bond is shown as a dashed line.

In the crystal, weak C—H⋯O hydrogen bonds link the molecules into infinite chains propagating along the c-axis direction (Fig. 2). Further, there are π–π interactions between the almost parallel phenyl rings with centroid-to-centroid distances of 3.7124 (6) Å, where the dihedral angle between the phenyl rings is 3.83 (1)° and the slippage is 1.192 Å. A weak C—H⋯π(ring) interaction (Table 1) is also observed.

Figure 2
The packing diagram of (I) viewed down the b-axis direction. Intramolecular O—H⋯O and intermolecular C—H⋯O hydrogen bonds are shown as dashed lines. H atoms not involved in these interactions have been omitted for clarity.

To confirm and quantifying the intermolecular interactions in the crystal of (I), a Hirshfeld surface analysis (Fig. 3) was carried out using Crystal Explorer 17.5 (Spackman et al., 2021 ). The overall two-dimensional fingerprint plot, Fig. 4a, and those delineated into H⋯H (48.2% of the surface), H⋯O/O⋯H (20.0%), H⋯C/C⋯H (16.5%), C⋯C (12.7%), C⋯O/O⋯C (2.6%) and O⋯O(0.1%) (McKinnon et al., 2007 ) are illustrated in Fig. 4b–g, respectively.

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

Figure 4
The full two-dimensional fingerprint plots for (I), showing (a) all interactions, and delineated into (b) H⋯H, (c) H⋯O/O⋯H, (d) H⋯C/C⋯H, (e) C⋯C, (f) C⋯O/O⋯C and (g) O⋯O interactions. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.

Synthesis and crystallization

To a solution of 2-hydroxyacetophenone (1.36 g, 10 mmol) in ethanol (10 ml) was added 0.1 ml of piperidine as catalyst and the mixture was stirred at room temperature for 0.5 h. Then, 3-methoxybenzaldehyde (1.36 g, 10 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. 359 K). ¹H NMR (300 MHz, acetone-d₆, p.p.m.): 3.7 (s, 3H, CH₃); 6.94 (d, 1H, CH, arom. ³J_H—H = 7.8 Hz); 7.2 (s, 1H, arom.), 7.3–7.4 (m, 5H, arom.), 7.6 (d, 1H, CH, ³J_H—H = 15.6 HZ); 7.8 (d, 1H, CH, ³J_H—H = 15.6 Hz); 7.9 (d, 1H, CH, arom. ³J_H—H = 7.7 Hz); 11.3 (s, 1H, OH). ¹³C NMR (75 MHz, acetone-d₆, p.p.m.): 55.1 (CH₃); 112.8 (CH, arom.); 115.7 (CH, arom.); 117.4 (CH, arom); 117.6 (CH, arom.); 119.3 (C_quat, arom.); 120.1 (δbCH); 121.1 (CH, arom.); 128.8 (CH, arom.); 129.3 (CH, arom.); 135.7 (C_quat, arom.); 136.2 (CH, arom.); 144.7 (=CH); 159.7 (C—O), 160.8 (C—O); 194.9 (CO).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₁₄O₃
M_r	254.27
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	10.72243 (10), 10.51268 (9), 22.22491 (18)
β (°)	99.4688 (8)
V (Å³)	2471.09 (4)
Z	8
Radiation type	Cu Kα
μ (mm⁻¹)	0.76
Crystal size (mm)	0.15 × 0.10 × 0.10

Data collection
Diffractometer	Rigaku XtaLAB Synergy-S, HyPix-6000HE area-detector
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.770, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14193, 2689, 2527
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.099, 1.06
No. of reflections	2689
No. of parameters	178
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.19
Computer programs: CrysAlis PRO (Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ) and SHELXTL (Sheldrick, 2015), SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 2427472

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314625001828/hb4506sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314625001828/hb4506Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314625001828/hb4506Isup3.cml

checkCIF report

Computing details top

(E)-1-(2-Hydroxyphenyl)-3-(3-methoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₆H₁₄O₃	F(000) = 1072
M_r = 254.27	D_x = 1.367 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
a = 10.72243 (10) Å	Cell parameters from 10243 reflections
b = 10.51268 (9) Å	θ = 4.0–79.8°
c = 22.22491 (18) Å	µ = 0.76 mm⁻¹
β = 99.4688 (8)°	T = 100 K
V = 2471.09 (4) Å³	Prism, colourless
Z = 8	0.15 × 0.10 × 0.10 mm

Data collection top

Rigaku XtaLAB Synergy-S, HyPix-6000HE area-detector diffractometer	2527 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube	R_int = 0.031
φ and ω scans	θ_max = 80.0°, θ_min = 4.0°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021)	h = −13→13
T_min = 0.770, T_max = 1.000	k = −8→13
14193 measured reflections	l = −28→28
2689 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.0493P)² + 1.7373P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
2689 reflections	Δρ_max = 0.26 e Å⁻³
178 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: dual	Extinction coefficient: 0.00040 (4)

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.

Refinement. The OH hydrogen atom was located in a difference Fourier map, and refined freely. The C-bound hydrogen atom positions were geometrically placed (C—H = 0.95–0.98 Å and refined using a riding model by applying the constraint of U_iso = k U_eq (C), where k = 1.5 for methyl H atoms and k = 1.2 for the other C-bound H atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.38451 (7)	0.58069 (7)	0.35542 (3)	0.02097 (19)
O2	0.33559 (8)	0.41446 (8)	0.27352 (3)	0.0227 (2)
H2	0.3655 (18)	0.489 (2)	0.2965 (9)	0.056 (5)*
O3	0.54949 (8)	1.01783 (8)	0.60473 (3)	0.0223 (2)
C1	0.34130 (9)	0.51250 (10)	0.39322 (5)	0.0169 (2)
C2	0.28385 (9)	0.38836 (10)	0.37447 (5)	0.0163 (2)
C3	0.28323 (10)	0.34535 (10)	0.31402 (5)	0.0178 (2)
C4	0.22718 (10)	0.22920 (11)	0.29458 (5)	0.0209 (2)
H4	0.2271	0.2010	0.2540	0.025*
C5	0.17196 (10)	0.15544 (10)	0.33442 (5)	0.0212 (2)
H5	0.1338	0.0767	0.3210	0.025*
C6	0.17186 (10)	0.19577 (11)	0.39429 (5)	0.0203 (2)
H6	0.1339	0.1445	0.4215	0.024*
C7	0.22712 (10)	0.31026 (10)	0.41383 (5)	0.0184 (2)
H7	0.2269	0.3370	0.4547	0.022*
C8	0.34912 (10)	0.55674 (10)	0.45654 (5)	0.0186 (2)
H8	0.3206	0.5031	0.4859	0.022*
C9	0.39600 (10)	0.67174 (10)	0.47329 (5)	0.0176 (2)
H9	0.4217	0.7228	0.4422	0.021*
C10	0.41176 (9)	0.72683 (10)	0.53452 (5)	0.0168 (2)
C11	0.47212 (10)	0.84450 (10)	0.54386 (5)	0.0178 (2)
H11	0.5011	0.8858	0.5107	0.021*
C12	0.49052 (10)	0.90231 (10)	0.60123 (5)	0.0180 (2)
C13	0.44902 (10)	0.84144 (11)	0.64993 (5)	0.0196 (2)
H13	0.4617	0.8797	0.6892	0.024*
C14	0.38859 (10)	0.72374 (11)	0.64062 (5)	0.0205 (2)
H14	0.3605	0.6822	0.6739	0.025*
C15	0.36886 (10)	0.66657 (10)	0.58381 (5)	0.0187 (2)
H15	0.3266	0.5870	0.5781	0.022*
C16	0.56917 (11)	1.08037 (11)	0.66276 (5)	0.0225 (2)
H16A	0.6094	1.1631	0.6591	0.034*
H16B	0.6239	1.0279	0.6926	0.034*
H16C	0.4876	1.0930	0.6764	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0264 (4)	0.0192 (4)	0.0185 (4)	−0.0042 (3)	0.0074 (3)	0.0001 (3)
O2	0.0306 (4)	0.0225 (4)	0.0164 (4)	−0.0047 (3)	0.0081 (3)	−0.0007 (3)
O3	0.0296 (4)	0.0177 (4)	0.0203 (4)	−0.0056 (3)	0.0059 (3)	−0.0032 (3)
C1	0.0165 (5)	0.0172 (5)	0.0172 (5)	0.0016 (4)	0.0034 (4)	0.0010 (4)
C2	0.0163 (5)	0.0158 (5)	0.0168 (5)	0.0023 (4)	0.0029 (4)	−0.0002 (4)
C3	0.0184 (5)	0.0187 (5)	0.0171 (5)	0.0020 (4)	0.0048 (4)	0.0010 (4)
C4	0.0244 (5)	0.0205 (5)	0.0183 (5)	0.0005 (4)	0.0046 (4)	−0.0038 (4)
C5	0.0213 (5)	0.0157 (5)	0.0268 (5)	−0.0009 (4)	0.0045 (4)	−0.0032 (4)
C6	0.0210 (5)	0.0173 (5)	0.0236 (5)	0.0000 (4)	0.0066 (4)	0.0019 (4)
C7	0.0207 (5)	0.0176 (5)	0.0173 (5)	0.0012 (4)	0.0046 (4)	0.0001 (4)
C8	0.0216 (5)	0.0178 (5)	0.0168 (5)	0.0007 (4)	0.0041 (4)	0.0012 (4)
C9	0.0179 (5)	0.0179 (5)	0.0178 (5)	0.0016 (4)	0.0053 (4)	0.0006 (4)
C10	0.0169 (5)	0.0161 (5)	0.0178 (5)	0.0022 (4)	0.0040 (4)	0.0004 (4)
C11	0.0197 (5)	0.0166 (5)	0.0179 (5)	0.0005 (4)	0.0060 (4)	0.0011 (4)
C12	0.0178 (5)	0.0154 (5)	0.0208 (5)	0.0009 (4)	0.0029 (4)	−0.0005 (4)
C13	0.0227 (5)	0.0202 (5)	0.0159 (5)	0.0013 (4)	0.0033 (4)	−0.0015 (4)
C14	0.0248 (5)	0.0198 (5)	0.0179 (5)	0.0006 (4)	0.0067 (4)	0.0028 (4)
C15	0.0219 (5)	0.0148 (5)	0.0199 (5)	−0.0006 (4)	0.0052 (4)	0.0005 (4)
C16	0.0255 (5)	0.0189 (5)	0.0219 (5)	−0.0019 (4)	0.0006 (4)	−0.0048 (4)

Geometric parameters (Å, º) top

O1—C1	1.2498 (13)	C8—C9	1.3384 (16)
O2—C3	1.3489 (13)	C8—H8	0.9500
O2—H2	0.96 (2)	C9—C10	1.4631 (14)
O3—C12	1.3654 (13)	C9—H9	0.9500
O3—C16	1.4321 (13)	C10—C11	1.3957 (15)
C1—C8	1.4714 (14)	C10—C15	1.4066 (14)
C1—C2	1.4737 (15)	C11—C12	1.3968 (14)
C2—C7	1.4087 (14)	C11—H11	0.9500
C2—C3	1.4165 (14)	C12—C13	1.3921 (15)
C3—C4	1.3977 (15)	C13—C14	1.3963 (16)
C4—C5	1.3815 (16)	C13—H13	0.9500
C4—H4	0.9500	C14—C15	1.3828 (15)
C5—C6	1.3967 (15)	C14—H14	0.9500
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.3797 (15)	C16—H16A	0.9800
C6—H6	0.9500	C16—H16B	0.9800
C7—H7	0.9500	C16—H16C	0.9800

C3—O2—H2	102.8 (12)	C8—C9—H9	116.7
C12—O3—C16	117.25 (8)	C10—C9—H9	116.7
O1—C1—C8	119.50 (10)	C11—C10—C15	119.11 (9)
O1—C1—C2	120.12 (9)	C11—C10—C9	117.96 (9)
C8—C1—C2	120.38 (9)	C15—C10—C9	122.93 (9)
C7—C2—C3	117.90 (9)	C10—C11—C12	120.91 (9)
C7—C2—C1	122.93 (9)	C10—C11—H11	119.5
C3—C2—C1	119.16 (9)	C12—C11—H11	119.5
O2—C3—C4	117.98 (9)	O3—C12—C13	124.67 (10)
O2—C3—C2	121.57 (10)	O3—C12—C11	115.69 (9)
C4—C3—C2	120.45 (10)	C13—C12—C11	119.64 (10)
C5—C4—C3	120.00 (10)	C12—C13—C14	119.47 (10)
C5—C4—H4	120.0	C12—C13—H13	120.3
C3—C4—H4	120.0	C14—C13—H13	120.3
C4—C5—C6	120.52 (10)	C15—C14—C13	121.20 (10)
C4—C5—H5	119.7	C15—C14—H14	119.4
C6—C5—H5	119.7	C13—C14—H14	119.4
C7—C6—C5	119.81 (10)	C14—C15—C10	119.66 (10)
C7—C6—H6	120.1	C14—C15—H15	120.2
C5—C6—H6	120.1	C10—C15—H15	120.2
C6—C7—C2	121.33 (10)	O3—C16—H16A	109.5
C6—C7—H7	119.3	O3—C16—H16B	109.5
C2—C7—H7	119.3	H16A—C16—H16B	109.5
C9—C8—C1	120.74 (10)	O3—C16—H16C	109.5
C9—C8—H8	119.6	H16A—C16—H16C	109.5
C1—C8—H8	119.6	H16B—C16—H16C	109.5
C8—C9—C10	126.64 (10)

O1—C1—C2—C7	−176.32 (10)	C2—C1—C8—C9	−177.00 (9)
C8—C1—C2—C7	4.13 (15)	C1—C8—C9—C10	−178.67 (9)
O1—C1—C2—C3	2.66 (15)	C8—C9—C10—C11	174.88 (10)
C8—C1—C2—C3	−176.89 (9)	C8—C9—C10—C15	−5.16 (17)
C7—C2—C3—O2	−179.98 (9)	C15—C10—C11—C12	0.19 (15)
C1—C2—C3—O2	0.99 (15)	C9—C10—C11—C12	−179.85 (9)
C7—C2—C3—C4	0.32 (15)	C16—O3—C12—C13	−0.29 (15)
C1—C2—C3—C4	−178.71 (9)	C16—O3—C12—C11	179.57 (9)
O2—C3—C4—C5	−179.76 (10)	C10—C11—C12—O3	−179.36 (9)
C2—C3—C4—C5	−0.04 (16)	C10—C11—C12—C13	0.50 (16)
C3—C4—C5—C6	−0.18 (17)	O3—C12—C13—C14	179.34 (10)
C4—C5—C6—C7	0.11 (17)	C11—C12—C13—C14	−0.51 (16)
C5—C6—C7—C2	0.18 (16)	C12—C13—C14—C15	−0.16 (16)
C3—C2—C7—C6	−0.39 (15)	C13—C14—C15—C10	0.86 (16)
C1—C2—C7—C6	178.60 (9)	C11—C10—C15—C14	−0.86 (15)
O1—C1—C8—C9	3.45 (16)	C9—C10—C15—C14	179.18 (10)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.96 (2)	1.61 (2)	2.5156 (10)	154.9 (19)
C14—H14···O2ⁱ	0.95	2.49	3.4220 (13)	167
C16—H16C···Cg1ⁱⁱ	0.98	2.71	3.5097 (13)	140

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

Acknowledgements

The authors' contributions are as follows. Conceptualizations, IGM and TH; methodology, FNN and AYZ; investigation, TH, VNK and IGM; writing (original draft), TH, VNK and IGM; writing (review and editing of the manuscript), TH and IGM; visualization, TH and FSK; funding acquisition, VNK, TH and ANB; resources, TH, VNK and FNN; supervision, FNN and TH.

Funding information

This paper was supported by Baku State University and the RUDN University Strategic Academic Leadership Program. TH is also grateful to Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004).

References

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