1-(4-Hydro­xy­phenyl)-3-phenyl­prop-2-en-1-one

In the title mol­ecule, C₁₅H₁₂O₂, the carbonyl group is in an s-cis conformation. The dihedral angle between the planes of the 4-hydroxy­phenyl group and the phenyl ring is 34.96 (10)°. Electron conjugation is observed between the central —CH=CH—C(=O)— group and the attached rings. The crystal structure is stabilized by O—H...O-type intermolecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.044
• wR factor = 0.129
• Data-to-parameter ratio = 13.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

It is well known that in ketones, the carbonyl group plays an important role in the antibacterial activity of chalcones. Earlier crystal structure studies of some of the α,β-unsaturated ketone derivatives (Shanmuga Sundara Raj et al., 1996, 1998) have shown that there are two possible conformational isomers of ketones, one corresponds to the s-cis and the other to the s-trans form.

The title compound, (I), assumes an s-cis conformation, as can be seen from the torsion angle C7—C8—C9—O1 of -11.4 (3)°. The dihedral angle between the 4-hydroxyphenyl and phenyl rings is 34.96 (10)°. The central –CH═CH—C(═O)- group is oriented at angles of 13.04 (19) and 25.19 (14)° with respect to the phenyl and 4-hydroxyphenyl rings, respectively. The lengths of the C6—C7 [1.468 (3) Å], C7—C8 [1.324 (3) Å], C8—C9 [1.475 (3) Å], C9—O1 [1.241 (2) Å] and C9—C10 [1.468 (3) Å] bonds indicate conjugation. The widening of the bond angle C6—C7—C8 to 126.6 (2)° may be due to the close approach (2.20 Å) of atoms H8 and H5. A slight increase in the bond angle C7—C8—C9 to 122.4 (2)° may be attributed to the short intramolecular non-bonded interaction between O1 and H7 (2.49 Å). The unsaturated ketone group is not strictly planar, as is evident from the torsion angles C15—C10—C9—C8 [155.73 (19)°], C10—C9—C8—C7 [168.50 (2)°], C9—C8—C7—C6 [-177.17 (19)°] and C8—C7—C6—C1 [170.50 (2)°]. The H atoms H7 and H8 are trans to each other. The crystal structure is stabilized by O—H···O-type intermolecular hydrogen bonds (Table 1).

S2. Experimental

NaOH (0.22 g) in alcohol solution (100 ml) was treated with 0.5 M 4-hydroxyacetophenone (6.8 g) and stirred well. 0.5 M of benzaldehyde (5.3 g) was added to the solution. Stirring was continued for 2 h. A viscous liquid was obtained when stirring was no longer effective. It was kept in a refrigerator overnight. A yellow crude product was obtained; yield (5.9 g). Compound (I) was recrystallized from the rectified spirit.

Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids and the atom-numbering scheme.

1-(4-Hydroxyphenyl)-3-phenyl-2-propenal

Crystal data

C15H12O2	Dx = 1.287 Mg m^−3
Mr = 224.25	Cu Kα radiation, λ = 1.54180 Å
Orthorhombic, Pbca	Cell parameters from 25 reflections
a = 8.4663 (10) Å	θ = 20–30°
b = 22.384 (2) Å	µ = 0.68 mm^−1
c = 12.216 (3) Å	T = 293 K
V = 2315.2 (6) Å^3	Rectangular, yellow
Z = 8	0.30 × 0.22 × 0.15 mm
F(000) = 944

Data collection

Enraf-Nonius CAD-4 diffractometer	1518 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 67.9°, θmin = 4.0°
ω–2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→26
Tmin = 0.822, Tmax = 0.905	l = −14→0
2107 measured reflections	2 standard reflections every 120 min
2107 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.0493P)^2 + 0.8408P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
2107 reflections	Δρmax = 0.15 e Å^−3
156 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0018 (3)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	−0.0431 (2)	0.12610 (7)	0.61789 (12)	0.0610 (5)
O2	0.3845 (2)	0.35874 (7)	0.59586 (12)	0.0666 (5)
H2A	0.4137	0.3589	0.5319	0.100*
C10	0.1188 (2)	0.20795 (9)	0.66607 (15)	0.0428 (5)
C6	−0.1178 (2)	0.07359 (9)	0.95098 (16)	0.0467 (5)
C9	0.0247 (2)	0.15458 (9)	0.69126 (16)	0.0468 (5)
C11	0.1465 (3)	0.25249 (10)	0.74367 (16)	0.0507 (5)
H11	0.1050	0.2482	0.8137	0.061*
C13	0.2987 (2)	0.30913 (9)	0.61535 (16)	0.0485 (5)
C15	0.1843 (2)	0.21562 (9)	0.56201 (16)	0.0466 (5)
H15	0.1666	0.1869	0.5085	0.056*
C14	0.2745 (2)	0.26497 (9)	0.53727 (15)	0.0486 (5)
H14	0.3193	0.2688	0.4681	0.058*
C12	0.2333 (3)	0.30244 (10)	0.71920 (16)	0.0566 (6)
H12	0.2486	0.3318	0.7720	0.068*
C7	−0.0908 (2)	0.09406 (9)	0.83833 (16)	0.0478 (5)
H7	−0.1518	0.0763	0.7840	0.057*
C8	0.0116 (3)	0.13520 (10)	0.80625 (16)	0.0512 (5)
H8	0.0777	0.1525	0.8581	0.061*
C1	−0.2448 (3)	0.03666 (11)	0.9737 (2)	0.0666 (7)
H1	−0.3089	0.0236	0.9167	0.080*
C5	−0.0229 (3)	0.09103 (11)	1.03738 (18)	0.0611 (6)
H5	0.0644	0.1152	1.0241	0.073*
C4	−0.0561 (3)	0.07298 (11)	1.14339 (19)	0.0694 (7)
H4	0.0082	0.0854	1.2008	0.083*
C2	−0.2777 (4)	0.01894 (13)	1.0799 (2)	0.0818 (9)
H2	−0.3645	−0.0053	1.0941	0.098*
C3	−0.1823 (4)	0.03712 (11)	1.1638 (2)	0.0738 (8)
H3	−0.2039	0.0249	1.2350	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0782 (11)	0.0629 (9)	0.0420 (8)	−0.0100 (9)	−0.0059 (8)	0.0045 (7)
O2	0.0833 (12)	0.0696 (10)	0.0469 (8)	−0.0219 (9)	0.0072 (8)	0.0022 (8)
C10	0.0417 (10)	0.0509 (11)	0.0358 (9)	0.0072 (9)	−0.0010 (8)	0.0054 (8)
C6	0.0532 (12)	0.0430 (10)	0.0439 (11)	0.0028 (10)	0.0072 (10)	0.0015 (9)
C9	0.0465 (11)	0.0535 (12)	0.0405 (10)	0.0065 (10)	−0.0008 (9)	0.0058 (9)
C11	0.0571 (12)	0.0612 (12)	0.0337 (9)	0.0035 (11)	0.0059 (9)	0.0042 (9)
C13	0.0503 (12)	0.0538 (12)	0.0414 (10)	−0.0014 (10)	−0.0005 (9)	0.0060 (9)
C15	0.0499 (11)	0.0546 (12)	0.0352 (10)	0.0047 (10)	−0.0008 (9)	0.0015 (9)
C14	0.0522 (12)	0.0621 (13)	0.0316 (9)	0.0015 (10)	0.0021 (9)	0.0049 (9)
C12	0.0698 (15)	0.0611 (13)	0.0390 (11)	−0.0037 (12)	0.0038 (11)	−0.0028 (9)
C7	0.0515 (12)	0.0503 (11)	0.0414 (11)	0.0025 (10)	0.0025 (9)	−0.0007 (9)
C8	0.0550 (12)	0.0595 (12)	0.0390 (10)	−0.0038 (11)	−0.0032 (9)	0.0082 (9)
C1	0.0760 (16)	0.0665 (15)	0.0574 (14)	−0.0186 (13)	0.0093 (13)	−0.0013 (12)
C5	0.0687 (15)	0.0663 (14)	0.0482 (12)	−0.0117 (12)	−0.0022 (11)	0.0102 (11)
C4	0.0887 (18)	0.0749 (16)	0.0446 (12)	−0.0011 (15)	−0.0037 (13)	0.0086 (12)
C2	0.095 (2)	0.0792 (18)	0.0711 (17)	−0.0236 (16)	0.0268 (16)	0.0107 (14)
C3	0.102 (2)	0.0694 (16)	0.0502 (14)	0.0049 (16)	0.0196 (14)	0.0137 (12)

Geometric parameters (Å, º)

O1—C9	1.241 (2)	C15—H15	0.93
O2—C13	1.348 (2)	C14—H14	0.93
O2—H2A	0.82	C12—H12	0.93
C10—C11	1.396 (3)	C7—C8	1.324 (3)
C10—C15	1.398 (3)	C7—H7	0.93
C10—C9	1.468 (3)	C8—H8	0.93
C6—C5	1.383 (3)	C1—C2	1.386 (3)
C6—C1	1.384 (3)	C1—H1	0.93
C6—C7	1.468 (3)	C5—C4	1.385 (3)
C9—C8	1.475 (3)	C5—H5	0.93
C11—C12	1.371 (3)	C4—C3	1.360 (4)
C11—H11	0.93	C4—H4	0.93
C13—C14	1.389 (3)	C2—C3	1.367 (4)
C13—C12	1.392 (3)	C2—H2	0.93
C15—C14	1.377 (3)	C3—H3	0.93
C13—O2—H2A	109.5	C11—C12—H12	120.0
C11—C10—C15	117.61 (19)	C13—C12—H12	120.0
C11—C10—C9	122.00 (18)	C8—C7—C6	126.6 (2)
C15—C10—C9	120.39 (18)	C8—C7—H7	116.7
C5—C6—C1	117.9 (2)	C6—C7—H7	116.7
C5—C6—C7	122.47 (19)	C7—C8—C9	122.4 (2)
C1—C6—C7	119.7 (2)	C7—C8—H8	118.8
O1—C9—C10	121.17 (18)	C9—C8—H8	118.8
O1—C9—C8	120.15 (19)	C6—C1—C2	121.0 (3)
C10—C9—C8	118.68 (18)	C6—C1—H1	119.5
C12—C11—C10	121.63 (19)	C2—C1—H1	119.5
C12—C11—H11	119.2	C6—C5—C4	120.9 (2)
C10—C11—H11	119.2	C6—C5—H5	119.6
O2—C13—C14	122.98 (18)	C4—C5—H5	119.6
O2—C13—C12	117.64 (19)	C3—C4—C5	120.2 (2)
C14—C13—C12	119.4 (2)	C3—C4—H4	119.9
C14—C15—C10	121.24 (19)	C5—C4—H4	119.9
C14—C15—H15	119.4	C3—C2—C1	119.9 (3)
C10—C15—H15	119.4	C3—C2—H2	120.0
C15—C14—C13	120.14 (18)	C1—C2—H2	120.0
C15—C14—H14	119.9	C4—C3—C2	120.2 (2)
C13—C14—H14	119.9	C4—C3—H3	119.9
C11—C12—C13	120.0 (2)	C2—C3—H3	119.9
C11—C10—C9—O1	155.7 (2)	C5—C6—C7—C8	−7.8 (4)
C15—C10—C9—O1	−24.4 (3)	C1—C6—C7—C8	170.5 (2)
C11—C10—C9—C8	−24.2 (3)	C6—C7—C8—C9	−177.17 (19)
C15—C10—C9—C8	155.73 (19)	O1—C9—C8—C7	−11.4 (3)
C15—C10—C11—C12	0.6 (3)	C10—C9—C8—C7	168.5 (2)
C9—C10—C11—C12	−179.4 (2)	C5—C6—C1—C2	1.5 (4)
C11—C10—C15—C14	0.8 (3)	C7—C6—C1—C2	−176.9 (2)
C9—C10—C15—C14	−179.15 (18)	C1—C6—C5—C4	−1.2 (4)
C10—C15—C14—C13	−1.7 (3)	C7—C6—C5—C4	177.1 (2)
O2—C13—C14—C15	−179.4 (2)	C6—C5—C4—C3	0.7 (4)
C12—C13—C14—C15	1.2 (3)	C6—C1—C2—C3	−1.2 (4)
C10—C11—C12—C13	−1.1 (3)	C5—C4—C3—C2	−0.3 (4)
O2—C13—C12—C11	−179.3 (2)	C1—C2—C3—C4	0.6 (4)
C14—C13—C12—C11	0.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1^i	0.82	1.90	2.704 (2)	168
C7—H7···O1	0.93	2.49	2.816 (3)	101

Symmetry code: (i) x+1/2, −y+1/2, −z+1.