2-(Furan-2-yl)-3-hy-droxy-4H-chromen-4-one.

In the crystal structure of the title compound, C(13)H(8)O(4), the inversely oriented mol-ecules form inversion dimers through pairs of O-H⋯O hydrogen-bonding inter-actions. An intramolecular O-H⋯O hydrogen bond occurs. In the packing of the mol-ecules, the nearly planar 2-(furan-2-yl)-4H-chromene units [dihedral angle between the chromene and furan rings = 3.8 (1)°] are either parallel or inclined at an angle of 80.7 (1)°.

Related literature

For general features of flavonols (derivatives of 3-hy­droxy-2-phenyl-4H-chromen-4-one), see: Klymchenko et al. (2003 ▶); Sengupta & Kasha (1979 ▶). For related structures, see: Etter et al. (1986 ▶); Waller et al. (2003 ▶). For inter­molecular inter­actions, see: Aakeröy et al. (1992 ▶); Novoa et al. (2006 ▶). For the synthesis, see: Klymchenko et al. (2003 ▶).

Experimental

Crystal data

C13H8O4

M = 228.19

Monoclinic,

a = 14.365 (8) Å

b = 4.421 (3) Å

c = 17.086 (10) Å

β = 110.91 (5)°

V = 1013.6 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.40 × 0.40 × 0.14 mm

Data collection

Kuma KM4 CCD κ-geometry diffractometer

7132 measured reflections

1779 independent reflections

1436 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.092

S = 1.10

1779 reflections

158 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2003 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2003 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810053596/ng5090sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053596/ng5090Isup2.hkl

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

C13H8O4	F(000) = 472
Mr = 228.19	Dx = 1.495 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1436 reflections
a = 14.365 (8) Å	θ = 3.4–25.0°
b = 4.421 (3) Å	µ = 0.11 mm−1
c = 17.086 (10) Å	T = 100 K
β = 110.91 (5)°	Plate, greenish-yellow
V = 1013.6 (11) Å3	0.40 × 0.40 × 0.14 mm
Z = 4

Kuma KM4 CCD κ-geometry diffractometer	1436 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
graphite	θmax = 25.0°, θmin = 3.4°
ω scans	h = −17→17
7132 measured reflections	k = −4→5
1779 independent reflections	l = −20→18

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0517P)2 + 0.0439P] where P = (Fo2 + 2Fc2)/3
1779 reflections	(Δ/σ)max < 0.001
158 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.21 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	0.30889 (8)	0.5549 (2)	0.43752 (6)	0.0209 (3)
C2	0.27113 (12)	0.6670 (4)	0.49500 (9)	0.0189 (4)
C3	0.17955 (12)	0.5867 (4)	0.49522 (9)	0.0192 (4)
C4	0.11644 (12)	0.3802 (4)	0.43368 (9)	0.0200 (4)
C5	0.10589 (12)	0.0603 (4)	0.30910 (9)	0.0212 (4)
H5	0.0416	−0.0076	0.3051	0.025*
C6	0.14678 (13)	−0.0412 (4)	0.25248 (10)	0.0232 (4)
H6	0.1102 (13)	−0.177 (4)	0.2072 (11)	0.028*
C7	0.24244 (13)	0.0564 (4)	0.25881 (10)	0.0248 (4)
H7	0.2707	−0.0148	0.2197	0.030*
C8	0.29541 (13)	0.2533 (4)	0.32077 (10)	0.0229 (4)
H8	0.3601	0.3182	0.3250	0.027*
C9	0.15832 (12)	0.2640 (4)	0.37305 (9)	0.0193 (4)
C10	0.25266 (12)	0.3566 (4)	0.37755 (9)	0.0189 (4)
O11	0.14832 (9)	0.7044 (3)	0.55453 (7)	0.0266 (3)
H11	0.0840 (16)	0.665 (5)	0.5432 (12)	0.040*
O12	0.03228 (8)	0.3089 (3)	0.43240 (7)	0.0277 (3)
C13	0.33852 (12)	0.8757 (4)	0.55296 (9)	0.0198 (4)
O14	0.42459 (8)	0.9419 (3)	0.53893 (7)	0.0245 (3)
C15	0.47607 (12)	1.1419 (4)	0.59996 (10)	0.0264 (4)
H15	0.5387	1.2273	0.6053	0.032*
C16	0.42634 (12)	1.2018 (4)	0.65152 (10)	0.0243 (4)
H16	0.4471	1.3323	0.6988	0.029*
C17	0.33603 (13)	1.0302 (4)	0.62119 (10)	0.0224 (4)
H17	0.2820 (13)	1.024 (4)	0.6427 (10)	0.027*

	U11	U22	U33	U12	U13	U23
O1	0.0202 (6)	0.0231 (6)	0.0215 (6)	−0.0020 (5)	0.0099 (5)	−0.0031 (5)
C2	0.0205 (9)	0.0197 (8)	0.0168 (8)	0.0034 (7)	0.0072 (7)	0.0038 (7)
C3	0.0188 (9)	0.0231 (9)	0.0162 (8)	0.0023 (7)	0.0069 (7)	0.0040 (7)
C4	0.0192 (9)	0.0211 (9)	0.0195 (8)	0.0019 (7)	0.0068 (7)	0.0053 (7)
C5	0.0186 (9)	0.0220 (9)	0.0212 (8)	0.0007 (7)	0.0050 (7)	0.0036 (7)
C6	0.0256 (10)	0.0219 (9)	0.0196 (9)	−0.0008 (7)	0.0049 (7)	0.0010 (7)
C7	0.0315 (10)	0.0231 (9)	0.0232 (9)	0.0034 (8)	0.0141 (8)	0.0014 (7)
C8	0.0208 (9)	0.0247 (9)	0.0257 (9)	−0.0013 (7)	0.0115 (7)	0.0014 (7)
C9	0.0198 (9)	0.0200 (9)	0.0170 (8)	0.0020 (7)	0.0051 (7)	0.0044 (6)
C10	0.0192 (8)	0.0180 (9)	0.0187 (8)	0.0010 (7)	0.0055 (7)	0.0028 (7)
O11	0.0201 (7)	0.0390 (8)	0.0226 (6)	−0.0047 (6)	0.0100 (5)	−0.0072 (5)
O12	0.0202 (7)	0.0377 (7)	0.0265 (6)	−0.0055 (5)	0.0099 (5)	−0.0040 (5)
C13	0.0164 (8)	0.0223 (9)	0.0207 (8)	0.0020 (7)	0.0066 (7)	0.0059 (7)
O14	0.0203 (6)	0.0280 (7)	0.0265 (6)	−0.0054 (5)	0.0100 (5)	−0.0047 (5)
C15	0.0201 (9)	0.0258 (10)	0.0290 (9)	−0.0055 (7)	0.0037 (7)	−0.0052 (8)
C16	0.0259 (9)	0.0228 (9)	0.0219 (8)	0.0000 (7)	0.0056 (7)	−0.0004 (7)
C17	0.0221 (9)	0.0238 (9)	0.0211 (8)	0.0022 (7)	0.0075 (7)	0.0021 (7)

O1—C10	1.371 (2)	C7—H7	0.9500
O1—C2	1.3729 (19)	C8—C10	1.397 (2)
C2—C3	1.364 (2)	C8—H8	0.9500
C2—C13	1.444 (2)	C9—C10	1.391 (2)
C3—O11	1.3503 (19)	O11—H11	0.89 (2)
C3—C4	1.443 (2)	C13—C17	1.362 (2)
C4—O12	1.2419 (19)	C13—O14	1.372 (2)
C4—C9	1.464 (2)	O14—C15	1.366 (2)
C5—C6	1.374 (2)	C15—C16	1.344 (2)
C5—C9	1.409 (2)	C15—H15	0.9500
C5—H5	0.9500	C16—C17	1.431 (3)
C6—C7	1.407 (2)	C16—H16	0.9500
C6—H6	0.971 (18)	C17—H17	0.971 (17)
C7—C8	1.372 (2)
C10—O1—C2	119.19 (13)	C10—C8—H8	120.6
C3—C2—O1	122.39 (15)	C10—C9—C5	118.13 (15)
C3—C2—C13	125.15 (14)	C10—C9—C4	119.72 (15)
O1—C2—C13	112.46 (14)	C5—C9—C4	122.15 (15)
O11—C3—C2	118.75 (15)	O1—C10—C9	122.13 (14)
O11—C3—C4	120.01 (14)	O1—C10—C8	116.11 (14)
C2—C3—C4	121.24 (14)	C9—C10—C8	121.76 (15)
O12—C4—C3	121.87 (15)	C3—O11—H11	110.9 (13)
O12—C4—C9	122.81 (15)	C17—C13—O14	110.06 (15)
C3—C4—C9	115.33 (14)	C17—C13—C2	133.72 (16)
C6—C5—C9	120.69 (16)	O14—C13—C2	116.21 (14)
C6—C5—H5	119.7	C15—O14—C13	106.30 (13)
C9—C5—H5	119.7	C16—C15—O14	111.01 (15)
C5—C6—C7	119.78 (16)	C16—C15—H15	124.5
C5—C6—H6	121.1 (10)	O14—C15—H15	124.5
C7—C6—H6	119.1 (10)	C15—C16—C17	106.47 (15)
C8—C7—C6	120.76 (15)	C15—C16—H16	126.8
C8—C7—H7	119.6	C17—C16—H16	126.8
C6—C7—H7	119.6	C13—C17—C16	106.17 (16)
C7—C8—C10	118.87 (16)	C13—C17—H17	125.5 (10)
C7—C8—H8	120.6	C16—C17—H17	128.4 (10)
C10—O1—C2—C3	0.5 (2)	C2—O1—C10—C9	−0.2 (2)
C10—O1—C2—C13	−179.14 (13)	C2—O1—C10—C8	179.56 (13)
O1—C2—C3—O11	179.20 (13)	C5—C9—C10—O1	179.80 (14)
C13—C2—C3—O11	−1.2 (2)	C4—C9—C10—O1	0.1 (2)
O1—C2—C3—C4	−0.8 (2)	C5—C9—C10—C8	0.1 (2)
C13—C2—C3—C4	178.82 (14)	C4—C9—C10—C8	−179.59 (14)
O11—C3—C4—O12	1.2 (2)	C7—C8—C10—O1	−179.42 (14)
C2—C3—C4—O12	−178.86 (15)	C7—C8—C10—C9	0.3 (2)
O11—C3—C4—C9	−179.30 (13)	C3—C2—C13—C17	3.7 (3)
C2—C3—C4—C9	0.7 (2)	O1—C2—C13—C17	−176.67 (16)
C9—C5—C6—C7	0.7 (2)	C3—C2—C13—O14	−175.90 (14)
C5—C6—C7—C8	−0.3 (2)	O1—C2—C13—O14	3.73 (19)
C6—C7—C8—C10	−0.2 (2)	C17—C13—O14—C15	−0.06 (17)
C6—C5—C9—C10	−0.6 (2)	C2—C13—O14—C15	179.64 (13)
C6—C5—C9—C4	179.08 (14)	C13—O14—C15—C16	0.35 (18)
O12—C4—C9—C10	179.17 (14)	O14—C15—C16—C17	−0.49 (19)
C3—C4—C9—C10	−0.4 (2)	O14—C13—C17—C16	−0.23 (18)
O12—C4—C9—C5	−0.5 (2)	C2—C13—C17—C16	−179.85 (17)
C3—C4—C9—C5	179.98 (14)	C15—C16—C17—C13	0.44 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O12i	0.97 (2)	2.53 (2)	3.352 (3)	142 (2)
O11—H11···O12	0.89 (2)	2.37 (2)	2.776 (3)	108 (2)
O11—H11···O12ii	0.89 (2)	1.87 (2)	2.683 (3)	152 (2)
C17—H17···O11	0.97 (2)	2.43 (2)	2.907 (3)	110 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O12i	0.97 (2)	2.53 (2)	3.352 (3)	142 (2)
O11—H11⋯O12	0.89 (2)	2.37 (2)	2.776 (3)	108 (2)
O11—H11⋯O12ii	0.89 (2)	1.87 (2)	2.683 (3)	152 (2)

Symmetry codes: (i) ; (ii) .