(E)-3-(2-Fur-yl)-1-(2-hydroxy-phen-yl)prop-2-en-1-one.

In the title mol-ecule, C(13)H(10)O(3), an intra-molecular O-H⋯O hydrogen bond influences the mol-ecular conformation, and the benzene and furan rings form a dihedral angle of 8.35 (7)°. Weak inter-molecular C-H⋯O hydrogen bonds link mol-ecules into sheets parallel to the bc plane.

Related literature

For a related crystal structure, see: Li et al. (1992 ▶).

Experimental

Crystal data

C13H10O3

M = 214.21

Monoclinic,

a = 3.8560 (5) Å

b = 15.6565 (14) Å

c = 17.309 (2) Å

β = 95.065 (2)°

V = 1040.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 (2) K

0.27 × 0.25 × 0.07 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.974, T max = 0.993

5153 measured reflections

1848 independent reflections

668 reflections with I > 2σ(I)

R int = 0.126

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.184

S = 0.81

1848 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031644/cv2448sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031644/cv2448Isup2.hkl

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

C13H10O3	F(000) = 448
Mr = 214.21	Dx = 1.367 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 3.8560 (5) Å	Cell parameters from 438 reflections
b = 15.6565 (14) Å	θ = 2.4–18.4°
c = 17.309 (2) Å	µ = 0.10 mm−1
β = 95.065 (2)°	T = 298 K
V = 1040.9 (2) Å3	Block, colourless
Z = 4	0.27 × 0.25 × 0.07 mm

Siemens SMART CCD area-detector diffractometer	1848 independent reflections
Radiation source: fine-focus sealed tube	668 reflections with I > 2σ(I)
graphite	Rint = 0.126
Detector resolution: φ and ω pixels mm-1	θmax = 25.0°, θmin = 1.8°
φ and ω scans	h = −4→4
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −7→18
Tmin = 0.974, Tmax = 0.993	l = −20→20
5153 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184	H-atom parameters constrained
S = 0.81	w = 1/[σ2(Fo2) + (0.0721P)2] where P = (Fo2 + 2Fc2)/3
1848 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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
O1	1.0561 (7)	0.73465 (16)	0.48262 (15)	0.0794 (9)
O2	0.8017 (8)	0.83794 (18)	0.74522 (15)	0.0885 (11)
O3	0.5477 (10)	0.9672 (2)	0.80912 (17)	0.1030 (12)
H3	0.6546	0.9220	0.8087	0.154*
C1	1.1454 (12)	0.6735 (3)	0.4327 (2)	0.0842 (15)
H1	1.1472	0.6811	0.3794	0.101*
C2	1.2297 (11)	0.6018 (3)	0.4699 (3)	0.0769 (13)
H2	1.3018	0.5510	0.4485	0.092*
C3	1.1887 (11)	0.6177 (3)	0.5478 (2)	0.0748 (13)
H3A	1.2271	0.5788	0.5882	0.090*
C4	1.0842 (10)	0.6991 (2)	0.5544 (2)	0.0584 (10)
C5	0.9983 (9)	0.7493 (2)	0.6177 (2)	0.0608 (11)
H5	1.0222	0.7240	0.6665	0.073*
C6	0.8860 (10)	0.8300 (2)	0.6137 (2)	0.0598 (11)
H6	0.8676	0.8578	0.5661	0.072*
C7	0.7918 (10)	0.8754 (2)	0.6822 (2)	0.0600 (11)
C8	0.6700 (9)	0.9648 (2)	0.6757 (2)	0.0553 (10)
C9	0.5559 (11)	1.0064 (3)	0.7399 (2)	0.0690 (12)
C10	0.4467 (12)	1.0901 (3)	0.7358 (3)	0.0835 (14)
H10	0.3697	1.1170	0.7790	0.100*
C11	0.4529 (13)	1.1329 (3)	0.6679 (3)	0.0930 (16)
H11	0.3769	1.1893	0.6649	0.112*
C12	0.5685 (12)	1.0951 (3)	0.6033 (3)	0.0839 (14)
H12	0.5747	1.1256	0.5573	0.101*
C13	0.6745 (11)	1.0117 (3)	0.6079 (2)	0.0702 (12)
H13	0.7518	0.9858	0.5642	0.084*

	U11	U22	U33	U12	U13	U23
O1	0.111 (3)	0.0632 (19)	0.0648 (18)	0.0106 (16)	0.0132 (16)	−0.0022 (16)
O2	0.138 (3)	0.067 (2)	0.0625 (18)	0.0095 (18)	0.0190 (18)	0.0029 (15)
O3	0.150 (4)	0.087 (3)	0.076 (2)	0.010 (2)	0.033 (2)	−0.0105 (18)
C1	0.112 (4)	0.076 (3)	0.065 (3)	0.008 (3)	0.015 (3)	−0.014 (3)
C2	0.080 (4)	0.057 (3)	0.095 (3)	0.008 (2)	0.012 (3)	−0.016 (3)
C3	0.086 (4)	0.061 (3)	0.078 (3)	0.008 (2)	0.011 (2)	−0.004 (2)
C4	0.065 (3)	0.053 (2)	0.058 (2)	−0.002 (2)	0.010 (2)	−0.001 (2)
C5	0.063 (3)	0.059 (2)	0.061 (2)	0.001 (2)	0.010 (2)	0.004 (2)
C6	0.067 (3)	0.058 (2)	0.054 (2)	0.002 (2)	0.005 (2)	−0.003 (2)
C7	0.064 (3)	0.057 (3)	0.059 (2)	−0.005 (2)	0.004 (2)	0.001 (2)
C8	0.055 (3)	0.053 (2)	0.058 (2)	−0.0020 (19)	0.006 (2)	−0.001 (2)
C9	0.071 (3)	0.069 (3)	0.068 (3)	−0.001 (2)	0.009 (2)	−0.009 (2)
C10	0.080 (4)	0.073 (3)	0.095 (4)	0.008 (3)	0.001 (3)	−0.023 (3)
C11	0.093 (4)	0.061 (3)	0.122 (4)	0.014 (3)	−0.014 (3)	−0.013 (3)
C12	0.099 (4)	0.063 (3)	0.086 (3)	0.000 (3)	−0.008 (3)	0.007 (3)
C13	0.078 (3)	0.056 (3)	0.076 (3)	−0.004 (2)	0.007 (2)	−0.005 (2)

O1—C1	1.354 (4)	C6—C7	1.455 (5)
O1—C4	1.357 (4)	C6—H6	0.9300
O2—C7	1.237 (4)	C7—C8	1.476 (5)
O3—C9	1.349 (4)	C8—C13	1.386 (5)
O3—H3	0.8200	C8—C9	1.393 (5)
C1—C2	1.321 (5)	C9—C10	1.377 (6)
C1—H1	0.9300	C10—C11	1.354 (5)
C2—C3	1.394 (5)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.374 (6)
C3—C4	1.343 (5)	C11—H11	0.9300
C3—H3A	0.9300	C12—C13	1.368 (5)
C4—C5	1.413 (5)	C12—H12	0.9300
C5—C6	1.335 (5)	C13—H13	0.9300
C5—H5	0.9300
C1—O1—C4	106.9 (3)	O2—C7—C8	120.1 (4)
C9—O3—H3	109.5	C6—C7—C8	120.1 (3)
C2—C1—O1	110.8 (3)	C13—C8—C9	117.1 (4)
C2—C1—H1	124.6	C13—C8—C7	122.6 (3)
O1—C1—H1	124.6	C9—C8—C7	120.3 (4)
C1—C2—C3	106.0 (4)	O3—C9—C10	116.6 (4)
C1—C2—H2	127.0	O3—C9—C8	122.0 (4)
C3—C2—H2	127.0	C10—C9—C8	121.4 (4)
C4—C3—C2	108.2 (4)	C11—C10—C9	119.2 (4)
C4—C3—H3A	125.9	C11—C10—H10	120.4
C2—C3—H3A	125.9	C9—C10—H10	120.4
C3—C4—O1	108.2 (3)	C10—C11—C12	121.6 (4)
C3—C4—C5	133.3 (4)	C10—C11—H11	119.2
O1—C4—C5	118.5 (3)	C12—C11—H11	119.2
C6—C5—C4	125.7 (3)	C13—C12—C11	118.8 (4)
C6—C5—H5	117.1	C13—C12—H12	120.6
C4—C5—H5	117.1	C11—C12—H12	120.6
C5—C6—C7	121.6 (3)	C12—C13—C8	122.0 (4)
C5—C6—H6	119.2	C12—C13—H13	119.0
C7—C6—H6	119.2	C8—C13—H13	119.0
O2—C7—C6	119.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.84	2.544 (4)	144
C1—H1···O2i	0.93	2.59	3.400 (5)	146
C3—H3A···O3ii	0.93	2.59	3.504 (5)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.82	1.84	2.544 (4)	144
C1—H1⋯O2i	0.93	2.59	3.400 (5)	146
C3—H3A⋯O3ii	0.93	2.59	3.504 (5)	169

Symmetry codes: (i) ; (ii) .