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

The title compound contains two almost coplanar phenyl rings and an intra­molecular O—H⋯O hydrogen bond.

Abstract

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.

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 ▸).

Figure 1.

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

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) ; (ii) .

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. 4 ▸a, 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. 4 ▸b–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 ▸)
Tmin, Tmax	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
Δρmax, Δρmin (e Å−3)	0.26, −0.19

Computer programs: CrysAlis PRO (Rigaku OD, 2021 ▸), SHELXT (Sheldrick, 2015a ▸), SHELXL (Sheldrick, 2015b ▸) and SHELXTL (Sheldrick, 2015), SHELXTL (Sheldrick, 2008 ▸).

Supplementary Material

CCDC reference: 2427472

Additional supporting information: crystallographic information; 3D view; checkCIF report

full crystallographic data

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

C16H14O3	F(000) = 1072
Mr = 254.27	Dx = 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

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

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

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

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(Fo2) + (0.0493P)2 + 1.7373P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2689 reflections	Δρmax = 0.26 e Å−3
178 parameters	Δρmin = −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)

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

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 Uiso = k Ueq (C), where k = 1.5 for methyl H atoms and k = 1.2 for the other C-bound H atoms.

(E)-1-(2-Hydroxyphenyl)-3-(3-methoxyphenyl)prop-2-en-1-one . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
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*

(E)-1-(2-Hydroxyphenyl)-3-(3-methoxyphenyl)prop-2-en-1-one . Atomic displacement parameters (Ų)

	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)

(E)-1-(2-Hydroxyphenyl)-3-(3-methoxyphenyl)prop-2-en-1-one . Geometric parameters (Å, º)

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)

(E)-1-(2-Hydroxyphenyl)-3-(3-methoxyphenyl)prop-2-en-1-one . Hydrogen-bond geometry (Å, º)

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.

Funding Statement

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).