5-Hydr-oxy-7-meth-oxy-4H-chromen-4-one.

The mol-ecular conformation of the title compound, C(10)H(8)O(4), isolated from Laretia acualis, is stabilized by a strong intra-molecular hydrogen bond between the hydroxyl and carbonyl groups. The crystal packing shows π-π stacking inter-actions. The chromene (4H-1-benzopyran-4-one) unit is essentially planar.

Related literature

For related literature, see: Gabor (1988 ▶); Valenti et al. (1993 ▶, 1998 ▶); Vasconcelos et al. (1998 ▶); Bernstein et al. (1995 ▶); Wickens (1995 ▶); Wallet & Cody (1995 ▶).

Experimental

Crystal data

C10H8O4

M = 192.16

Monoclinic,

a = 9.7551 (3) Å

b = 11.7512 (9) Å

c = 7.5211 (7) Å

β = 95.094 (4)°

V = 858.77 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 298 (2) K

0.19 × 0.10 × 0.08 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: none

1504 measured reflections

1504 independent reflections

1393 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.115

S = 1.08

1504 reflections

131 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.17 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO–SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807066494/bt2661sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066494/bt2661Isup2.hkl

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

C10H8O4	F000 = 400
Mr = 192.16	Dx = 1.486 Mg m−3
Monoclinic, P21/c	Melting point: 374 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 9.7551 (3) Å	Cell parameters from 1504 reflections
b = 11.7512 (9) Å	θ = 3.0–25.0º
c = 7.5211 (7) Å	µ = 0.12 mm−1
β = 95.094 (4)º	T = 298 (2) K
V = 858.77 (11) Å3	Prismatic, colourless
Z = 4	0.19 × 0.10 × 0.08 mm

Nonius KappaCCD area-detector diffractometer	1393 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0
Monochromator: graphite	θmax = 25.3º
φ scans, and ω scans with κ offsets	θmin = 3.2º
Absorption correction: none	h = −11→11
1504 measured reflections	k = −14→0
1504 independent reflections	l = 0→9

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.06P)2 + 0.1521P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.041	(Δ/σ)max < 0.001
wR(F2) = 0.115	Δρmax = 0.15 e Å−3
S = 1.08	Δρmin = −0.17 e Å−3
1504 reflections	Extinction correction: none
131 parameters

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	0.70907 (10)	0.05272 (8)	0.30079 (14)	0.0533 (3)
O2	0.96609 (11)	0.31131 (10)	0.18700 (17)	0.0649 (4)
O3	0.77689 (13)	0.45485 (9)	0.25771 (16)	0.0629 (4)
H9	0.855 (3)	0.422 (2)	0.219 (3)	0.098 (7)*
O4	0.36201 (10)	0.31332 (9)	0.43512 (14)	0.0558 (3)
C1	0.27108 (16)	0.22189 (16)	0.4674 (2)	0.0633 (5)
H1A	0.1856	0.2521	0.5006	0.095*
H1B	0.3121	0.175	0.5622	0.095*
H1C	0.2544	0.177	0.3609	0.095*
C2	0.83521 (16)	0.03322 (13)	0.2464 (2)	0.0586 (4)
H2	0.8626	−0.042	0.235	0.07*
C3	0.92292 (15)	0.11442 (14)	0.2080 (2)	0.0568 (4)
H3	1.0084	0.0946	0.1715	0.068*
C4	0.88700 (14)	0.23206 (12)	0.22245 (19)	0.0460 (4)
C4A	0.75193 (13)	0.25315 (10)	0.27872 (16)	0.0384 (3)
C5	0.69920 (14)	0.36468 (11)	0.29717 (17)	0.0427 (3)
C6	0.57034 (15)	0.38106 (12)	0.35134 (17)	0.0460 (4)
H6	0.5372	0.4545	0.3645	0.055*
C7	0.48861 (13)	0.28748 (12)	0.38688 (16)	0.0419 (3)
C8	0.53533 (13)	0.17729 (11)	0.37016 (17)	0.0419 (3)
H8	0.4808	0.1152	0.394	0.05*
C8A	0.66641 (13)	0.16281 (11)	0.31662 (17)	0.0391 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0439 (6)	0.0339 (5)	0.0831 (7)	0.0016 (4)	0.0111 (5)	−0.0009 (4)
O2	0.0439 (6)	0.0602 (7)	0.0922 (8)	−0.0118 (5)	0.0150 (5)	0.0044 (6)
O3	0.0628 (8)	0.0378 (6)	0.0895 (8)	−0.0086 (5)	0.0146 (6)	0.0063 (5)
O4	0.0431 (6)	0.0615 (7)	0.0646 (6)	0.0096 (5)	0.0145 (5)	−0.0015 (5)
C1	0.0409 (8)	0.0829 (12)	0.0677 (10)	−0.0004 (8)	0.0138 (7)	0.0061 (8)
C2	0.0456 (8)	0.0432 (8)	0.0876 (11)	0.0098 (6)	0.0105 (7)	−0.0038 (7)
C3	0.0376 (8)	0.0554 (9)	0.0779 (10)	0.0068 (7)	0.0087 (7)	−0.0033 (7)
C4	0.0357 (7)	0.0483 (8)	0.0536 (8)	−0.0036 (6)	0.0015 (5)	0.0015 (6)
C4A	0.0353 (7)	0.0387 (7)	0.0405 (6)	−0.0017 (5)	−0.0012 (5)	0.0006 (5)
C5	0.0458 (8)	0.0357 (7)	0.0458 (7)	−0.0036 (6)	0.0001 (5)	0.0023 (5)
C6	0.0501 (8)	0.0372 (7)	0.0502 (7)	0.0085 (6)	0.0026 (6)	−0.0011 (5)
C7	0.0376 (7)	0.0504 (8)	0.0374 (6)	0.0040 (6)	0.0020 (5)	−0.0012 (5)
C8	0.0380 (7)	0.0408 (7)	0.0470 (7)	−0.0039 (5)	0.0043 (5)	0.0015 (5)
C8A	0.0377 (7)	0.0347 (7)	0.0443 (7)	0.0007 (5)	0.0002 (5)	−0.0007 (5)

O1—C2	1.3503 (18)	C3—C4	1.433 (2)
O1—C8A	1.3674 (15)	C3—H3	0.93
O2—C4	1.2531 (17)	C4—C4A	1.4407 (19)
O3—C5	1.3510 (16)	C4A—C8A	1.3952 (18)
O3—H9	0.92 (2)	C4A—C5	1.4192 (18)
O4—C7	1.3522 (16)	C5—C6	1.369 (2)
O4—C1	1.428 (2)	C6—C7	1.398 (2)
C1—H1A	0.96	C6—H6	0.93
C1—H1B	0.96	C7—C8	1.3821 (19)
C1—H1C	0.96	C8—C8A	1.3848 (18)
C2—C3	1.330 (2)	C8—H8	0.93
C2—H2	0.93
C2—O1—C8A	118.65 (11)	C8A—C4A—C5	117.02 (12)
C5—O3—H9	103.8 (15)	C8A—C4A—C4	120.54 (12)
C7—O4—C1	118.20 (12)	C5—C4A—C4	122.44 (12)
O4—C1—H1A	109.5	O3—C5—C6	120.20 (12)
O4—C1—H1B	109.5	O3—C5—C4A	119.18 (13)
H1A—C1—H1B	109.5	C6—C5—C4A	120.62 (12)
O4—C1—H1C	109.5	C5—C6—C7	120.04 (12)
H1A—C1—H1C	109.5	C5—C6—H6	120
H1B—C1—H1C	109.5	C7—C6—H6	120
C3—C2—O1	124.40 (14)	O4—C7—C8	123.45 (13)
C3—C2—H2	117.8	O4—C7—C6	115.13 (12)
O1—C2—H2	117.8	C8—C7—C6	121.42 (12)
C2—C3—C4	120.62 (14)	C7—C8—C8A	117.52 (12)
C2—C3—H3	119.7	C7—C8—H8	121.2
C4—C3—H3	119.7	C8A—C8—H8	121.2
O2—C4—C3	122.79 (13)	O1—C8A—C8	115.95 (11)
O2—C4—C4A	122.08 (13)	O1—C8A—C4A	120.66 (12)
C3—C4—C4A	115.12 (12)	C8—C8A—C4A	123.38 (12)
C8A—O1—C2—C3	0.7 (2)	C1—O4—C7—C8	−1.15 (18)
O1—C2—C3—C4	−0.1 (3)	C1—O4—C7—C6	177.84 (12)
C2—C3—C4—O2	−179.70 (15)	C5—C6—C7—O4	−178.42 (11)
C2—C3—C4—C4A	−0.5 (2)	C5—C6—C7—C8	0.6 (2)
O2—C4—C4A—C8A	179.81 (12)	O4—C7—C8—C8A	178.87 (11)
C3—C4—C4A—C8A	0.59 (19)	C6—C7—C8—C8A	−0.05 (19)
O2—C4—C4A—C5	0.2 (2)	C2—O1—C8A—C8	179.00 (12)
C3—C4—C4A—C5	−178.99 (12)	C2—O1—C8A—C4A	−0.52 (19)
C8A—C4A—C5—O3	−178.38 (11)	C7—C8—C8A—O1	−179.75 (11)
C4—C4A—C5—O3	1.2 (2)	C7—C8—C8A—C4A	−0.24 (19)
C8A—C4A—C5—C6	0.52 (19)	C5—C4A—C8A—O1	179.50 (10)
C4—C4A—C5—C6	−179.88 (11)	C4—C4A—C8A—O1	−0.11 (19)
O3—C5—C6—C7	178.07 (11)	C5—C4A—C8A—C8	0.02 (19)
C4A—C5—C6—C7	−0.8 (2)	C4—C4A—C8A—C8	−179.59 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H9···O2	0.92 (3)	1.72 (3)	2.5901 (17)	155 (2)

CgI	CgJ	CgI···CgJ	Dihedral angle	Interplanar distance	Offset
Cg1	Cg2i	3.6661 (8)	1.39	3.508	1.13
Cg2	Cg1ii	3.6660 (8)	1.39	3.487	1.06
Cg2	Cg2i	3.7930 (8)	1.69	3.471	1.50
Cg2	Cg2ii	3.7931 (8)	1.69	3.486	1.53

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H9⋯O2	0.92 (3)	1.72 (3)	2.5901 (17)	155 (2)

Table 2

π–π interactions (Å,°)

Cg1 and Cg2 are the centroids of rings O1/C2–C4/C4A–C8A and C4A/C5–C8/C8A, respectively. The offset is defined as the distance between CgI and the perpendicular projection of CgJ on ring I.

CgI	CgJ	CgI⋯CgJ	Dihedral angle	Interplanar distance	Offset
Cg1	Cg2i	3.6661 (8)	1.39	3.51	1.13
Cg2	Cg1ii	3.6660 (8)	1.39	3.49	1.06
Cg2	Cg2i	3.7930 (8)	1.69	3.47	1.50
Cg2	Cg2ii	3.7931 (8)	1.69	3.49	1.53

Symmetry codes: (i) ; (ii) .