(2E,4E)-1-(2-Hy-droxy-phen-yl)-5-phenyl-penta-2,4-dien-1-one.

In the structure of the title chalcone, C(17)H(14)O(2), derived from cinnamaldehyde, the olefine group has a trans configuration. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯O hydrogen-bond inter-action with graph-set motif S(6).

Related literature

For the preparation, see: Lawrence et al. (2001 ▶). For related structures, see: Patil et al. (2007 ▶); Zhao et al. (2007 ▶). For standard bond lengths, see: Allen (2002 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related activity and structures, see: Dyrager et al. (2011 ▶); Jasinski et al. (2009 ▶); Ruan et al. (2011 ▶); Vencato et al. (2006 ▶).

Experimental

Crystal data

C17H14O2

M = 250.28

Orthorhombic,

a = 10.9068 (3) Å

b = 7.9851 (2) Å

c = 30.2131 (7) Å

V = 2631.32 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.39 × 0.17 × 0.09 mm

Data collection

Bruker X8 SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.92, T max = 0.99

18214 measured reflections

2691 independent reflections

1479 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.134

S = 1.01

2691 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2010) ▶.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681103025X/bx2361sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103025X/bx2361Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681103025X/bx2361Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H14O2	Dx = 1.264 Mg m−3
Mr = 250.28	Melting point: 428 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 10.9068 (3) Å	Cell parameters from 1573 reflections
b = 7.9851 (2) Å	θ = 2.7–19.5°
c = 30.2131 (7) Å	µ = 0.08 mm−1
V = 2631.32 (12) Å3	T = 296 K
Z = 8	Block, yellow
F(000) = 1056	0.39 × 0.17 × 0.09 mm

Bruker X8 SMART APEXII diffractometer	2691 independent reflections
graphite	1479 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm-1	Rint = 0.059
φ and ω scans	θmax = 26.4°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→11
Tmin = 0.92, Tmax = 0.99	k = −9→9
18214 measured reflections	l = −36→37

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H-atom parameters constrained
wR(F2) = 0.134	w = 1/[σ2(Fo2) + (0.0634P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
2691 reflections	Δρmax = 0.19 e Å−3
174 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0109 (11)

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.

	x	y	z	Uiso*/Ueq
O2	0.09900 (13)	0.62840 (18)	1.00369 (4)	0.0625 (4)
O1	0.07689 (13)	0.4619 (2)	1.07455 (5)	0.0652 (5)
H1	0.0543	0.5068	1.0515	0.098*
C12	0.27179 (18)	0.5570 (2)	1.04643 (6)	0.0443 (5)
C13	0.19982 (19)	0.4740 (2)	1.07803 (6)	0.0488 (5)
C11	0.21235 (18)	0.6346 (2)	1.00794 (6)	0.0472 (5)
C9	0.23958 (18)	0.7440 (2)	0.93309 (6)	0.0511 (5)
H9	0.1581	0.7152	0.9281	0.061*
C1	0.33154 (19)	0.8908 (3)	0.81740 (6)	0.0532 (5)
C10	0.28508 (18)	0.7155 (2)	0.97335 (6)	0.0515 (5)
H10	0.3651	0.748	0.9796	0.062*
C17	0.39835 (19)	0.5612 (3)	1.05313 (7)	0.0567 (6)
H17	0.4476	0.6164	1.0327	0.068*
C8	0.30670 (19)	0.8155 (2)	0.89703 (6)	0.0535 (5)
H8	0.3844	0.8579	0.903	0.064*
C7	0.26596 (19)	0.8255 (2)	0.85581 (7)	0.0554 (6)
H7	0.1868	0.7866	0.8508	0.066*
C6	0.4439 (2)	0.9703 (3)	0.82097 (7)	0.0620 (6)
H6	0.4796	0.9844	0.8487	0.074*
C5	0.5037 (2)	1.0290 (3)	0.78378 (8)	0.0762 (7)
H5	0.5794	1.0815	0.7866	0.091*
C15	0.3789 (2)	0.4036 (3)	1.11921 (7)	0.0686 (6)
H15	0.4151	0.3511	1.1434	0.082*
C16	0.4517 (2)	0.4863 (3)	1.08888 (7)	0.0671 (6)
H16	0.5362	0.491	1.0928	0.081*
C14	0.2542 (2)	0.3976 (3)	1.11417 (7)	0.0627 (6)
H14	0.2062	0.3423	1.135	0.075*
C2	0.2808 (2)	0.8734 (3)	0.77533 (7)	0.0663 (7)
H2	0.2052	0.8209	0.7721	0.08*
C3	0.3414 (3)	0.9331 (3)	0.73832 (7)	0.0791 (8)
H3	0.3065	0.9205	0.7104	0.095*
C4	0.4522 (3)	1.0105 (4)	0.74271 (8)	0.0822 (8)
H4	0.4929	1.0507	0.7178	0.099*

	U11	U22	U33	U12	U13	U23
O2	0.0432 (9)	0.0774 (10)	0.0669 (10)	−0.0019 (7)	−0.0019 (7)	0.0144 (7)
O1	0.0552 (10)	0.0791 (11)	0.0615 (10)	−0.0017 (8)	0.0075 (7)	0.0119 (8)
C12	0.0438 (13)	0.0442 (11)	0.0450 (11)	0.0031 (9)	0.0010 (9)	−0.0063 (9)
C13	0.0491 (13)	0.0487 (11)	0.0485 (11)	0.0033 (10)	0.0014 (10)	−0.0078 (9)
C11	0.0418 (12)	0.0468 (11)	0.0529 (12)	−0.0010 (9)	0.0037 (10)	−0.0051 (9)
C9	0.0454 (13)	0.0494 (12)	0.0585 (13)	0.0008 (10)	0.0042 (10)	−0.0005 (10)
C1	0.0542 (15)	0.0540 (12)	0.0515 (13)	0.0060 (11)	0.0009 (10)	0.0018 (9)
C10	0.0447 (13)	0.0557 (12)	0.0540 (12)	−0.0048 (10)	−0.0008 (10)	−0.0004 (10)
C17	0.0505 (14)	0.0619 (14)	0.0577 (13)	0.0023 (10)	−0.0012 (11)	−0.0059 (10)
C8	0.0468 (12)	0.0561 (12)	0.0577 (13)	−0.0039 (10)	0.0033 (10)	0.0043 (10)
C7	0.0499 (13)	0.0580 (13)	0.0583 (13)	−0.0028 (10)	−0.0025 (11)	0.0024 (10)
C6	0.0575 (15)	0.0729 (15)	0.0555 (14)	−0.0001 (12)	0.0010 (11)	0.0080 (11)
C5	0.0616 (16)	0.0920 (18)	0.0748 (17)	0.0004 (13)	0.0064 (13)	0.0201 (14)
C15	0.0813 (19)	0.0689 (14)	0.0555 (14)	0.0150 (13)	−0.0163 (13)	−0.0059 (12)
C16	0.0564 (15)	0.0764 (16)	0.0684 (16)	0.0061 (12)	−0.0148 (12)	−0.0087 (13)
C14	0.0792 (17)	0.0614 (14)	0.0476 (12)	0.0033 (12)	0.0012 (12)	−0.0001 (10)
C2	0.0660 (16)	0.0763 (16)	0.0566 (14)	0.0051 (12)	−0.0074 (12)	0.0013 (11)
C3	0.086 (2)	0.101 (2)	0.0504 (14)	0.0173 (16)	−0.0046 (13)	0.0067 (13)
C4	0.0790 (19)	0.107 (2)	0.0610 (17)	0.0177 (16)	0.0127 (14)	0.0238 (14)

O2—C11	1.244 (2)	C8—C7	1.324 (3)
O1—C13	1.348 (2)	C8—H8	0.93
O1—H1	0.82	C7—H7	0.93
C12—C17	1.395 (3)	C6—C5	1.381 (3)
C12—C13	1.402 (3)	C6—H6	0.93
C12—C11	1.469 (3)	C5—C4	1.370 (3)
C13—C14	1.384 (3)	C5—H5	0.93
C11—C10	1.463 (3)	C15—C14	1.369 (3)
C9—C10	1.333 (2)	C15—C16	1.381 (3)
C9—C8	1.431 (3)	C15—H15	0.93
C9—H9	0.93	C16—H16	0.93
C1—C6	1.385 (3)	C14—H14	0.93
C1—C2	1.393 (3)	C2—C3	1.383 (3)
C1—C7	1.460 (3)	C2—H2	0.93
C10—H10	0.93	C3—C4	1.364 (3)
C17—C16	1.365 (3)	C3—H3	0.93
C17—H17	0.93	C4—H4	0.93
C13—O1—H1	109.5	C8—C7—H7	116.4
C17—C12—C13	117.80 (18)	C1—C7—H7	116.4
C17—C12—C11	122.77 (18)	C5—C6—C1	120.6 (2)
C13—C12—C11	119.44 (18)	C5—C6—H6	119.7
O1—C13—C14	117.13 (19)	C1—C6—H6	119.7
O1—C13—C12	122.51 (18)	C4—C5—C6	120.5 (2)
C14—C13—C12	120.4 (2)	C4—C5—H5	119.7
O2—C11—C10	118.87 (17)	C6—C5—H5	119.7
O2—C11—C12	120.23 (17)	C14—C15—C16	120.9 (2)
C10—C11—C12	120.87 (17)	C14—C15—H15	119.5
C10—C9—C8	124.9 (2)	C16—C15—H15	119.5
C10—C9—H9	117.6	C17—C16—C15	119.3 (2)
C8—C9—H9	117.6	C17—C16—H16	120.3
C6—C1—C2	117.93 (19)	C15—C16—H16	120.3
C6—C1—C7	122.38 (18)	C15—C14—C13	119.9 (2)
C2—C1—C7	119.7 (2)	C15—C14—H14	120.1
C9—C10—C11	121.70 (19)	C13—C14—H14	120.1
C9—C10—H10	119.2	C3—C2—C1	120.9 (2)
C11—C10—H10	119.2	C3—C2—H2	119.5
C16—C17—C12	121.7 (2)	C1—C2—H2	119.5
C16—C17—H17	119.1	C4—C3—C2	120.0 (2)
C12—C17—H17	119.1	C4—C3—H3	120.0
C7—C8—C9	124.6 (2)	C2—C3—H3	120.0
C7—C8—H8	117.7	C3—C4—C5	120.0 (2)
C9—C8—H8	117.7	C3—C4—H4	120.0
C8—C7—C1	127.2 (2)	C5—C4—H4	120.0
C17—C12—C13—O1	−179.60 (17)	C6—C1—C7—C8	−7.7 (3)
C11—C12—C13—O1	0.2 (3)	C2—C1—C7—C8	172.1 (2)
C17—C12—C13—C14	−0.8 (3)	C2—C1—C6—C5	−0.5 (3)
C11—C12—C13—C14	178.95 (17)	C7—C1—C6—C5	179.4 (2)
C17—C12—C11—O2	−179.47 (18)	C1—C6—C5—C4	0.5 (4)
C13—C12—C11—O2	0.8 (3)	C12—C17—C16—C15	0.3 (3)
C17—C12—C11—C10	2.5 (3)	C14—C15—C16—C17	−0.9 (3)
C13—C12—C11—C10	−177.20 (17)	C16—C15—C14—C13	0.6 (3)
C8—C9—C10—C11	−177.06 (18)	O1—C13—C14—C15	179.10 (18)
O2—C11—C10—C9	−17.4 (3)	C12—C13—C14—C15	0.2 (3)
C12—C11—C10—C9	160.63 (18)	C6—C1—C2—C3	0.3 (3)
C13—C12—C17—C16	0.5 (3)	C7—C1—C2—C3	−179.6 (2)
C11—C12—C17—C16	−179.20 (18)	C1—C2—C3—C4	−0.1 (4)
C10—C9—C8—C7	171.7 (2)	C2—C3—C4—C5	0.0 (4)
C9—C8—C7—C1	−177.45 (19)	C6—C5—C4—C3	−0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.81	2.5317 (19)	146.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.81	2.5317 (19)	146