6,8-Dihydr-oxy-3-methyl-isocoumarin.

The title compound, C(10)H(8)O(4), was isolated from the fermentation culture of the endophytic fungus Cephalo-sporium sp. In the crystal structure, mol-ecules are connected into a one-dimensional chain along [101] by inter-molecular O-H⋯O hydrogen bonds involving the hydroxyl and carbonyl functionalities. The chains are linked by non-classical C-H⋯O inter-actions, forming extended two-dimensional layers approximately parallel to (11).

Related literature

For new bioactive secondary metabolites from marine fungi, see: Shao et al. (2007 ▶). For the investigation of an endophytic strain Cephalosporium sp., see: Wei et al. (2008 ▶); Hemingway et al. (1977 ▶); Kendall et al. (1989 ▶). For crystal structures with non-classical C—H⋯O inter­actions, see: Nangia (2002 ▶).

Experimental

Crystal data

C10H8O4

M = 192.16

Monoclinic,

a = 3.8201 (7) Å

b = 15.710 (3) Å

c = 14.196 (2) Å

β = 92.668 (2)°

V = 851.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 291 K

0.27 × 0.20 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.969, T max = 0.978

4781 measured reflections

1586 independent reflections

1272 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.094

S = 1.04

1586 reflections

131 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008083/bh2219sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008083/bh2219Isup2.hkl

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

C10H8O4	F(000) = 400
Mr = 192.16	Dx = 1.500 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1738 reflections
a = 3.8201 (7) Å	θ = 2.6–25.5°
b = 15.710 (3) Å	µ = 0.12 mm−1
c = 14.196 (2) Å	T = 291 K
β = 92.668 (2)°	Block, yellow
V = 851.1 (3) Å3	0.27 × 0.20 × 0.19 mm
Z = 4

Bruker APEXII CCD diffractometer	1586 independent reflections
Radiation source: fine-focus sealed tube	1272 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→4
Tmin = 0.969, Tmax = 0.978	k = −19→13
4781 measured reflections	l = −17→17

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0441P)2 + 0.1957P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
1586 reflections	Δρmax = 0.18 e Å−3
131 parameters	Δρmin = −0.14 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.015 (3)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
O1	0.3482 (3)	0.32453 (7)	0.81217 (7)	0.0451 (3)
O2	0.3544 (3)	0.19366 (7)	0.75748 (8)	0.0572 (4)
O3	0.0718 (3)	0.15766 (7)	0.58873 (8)	0.0552 (4)
H3	0.1709	0.1476	0.6400	0.083*
O4	−0.4021 (3)	0.39231 (7)	0.41364 (7)	0.0487 (3)
H4	−0.4514	0.3541	0.3759	0.073*
C1	0.3853 (4)	0.45742 (12)	0.89102 (11)	0.0516 (4)
H1A	0.3148	0.5160	0.8859	0.077*
H1B	0.6359	0.4542	0.8987	0.077*
H1C	0.2819	0.4321	0.9446	0.077*
C2	0.2659 (4)	0.41080 (10)	0.80372 (10)	0.0395 (4)
C3	0.1028 (4)	0.44079 (10)	0.72629 (10)	0.0379 (4)
H3A	0.0505	0.4985	0.7224	0.046*
C4	0.0042 (3)	0.38590 (9)	0.64774 (9)	0.0318 (3)
C5	−0.1641 (4)	0.41528 (9)	0.56587 (10)	0.0355 (3)
H5	−0.2230	0.4725	0.5598	0.043*
C6	−0.2453 (4)	0.35866 (10)	0.49244 (10)	0.0354 (3)
C7	−0.1659 (4)	0.27235 (9)	0.50066 (10)	0.0378 (4)
H7	−0.2235	0.2354	0.4512	0.045*
C8	−0.0016 (4)	0.24192 (9)	0.58233 (10)	0.0368 (3)
C9	0.0880 (4)	0.29837 (9)	0.65755 (9)	0.0337 (3)
C10	0.2651 (4)	0.26818 (10)	0.74166 (10)	0.0401 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0531 (7)	0.0503 (7)	0.0308 (5)	0.0018 (5)	−0.0102 (5)	−0.0008 (5)
O2	0.0802 (9)	0.0448 (7)	0.0447 (7)	0.0086 (6)	−0.0182 (6)	0.0060 (5)
O3	0.0804 (9)	0.0330 (6)	0.0503 (7)	0.0065 (5)	−0.0162 (6)	−0.0011 (5)
O4	0.0677 (8)	0.0425 (6)	0.0342 (6)	0.0033 (5)	−0.0174 (5)	−0.0004 (5)
C1	0.0488 (10)	0.0661 (11)	0.0390 (9)	−0.0024 (8)	−0.0060 (7)	−0.0131 (8)
C2	0.0382 (8)	0.0459 (9)	0.0344 (8)	−0.0026 (7)	0.0008 (6)	−0.0058 (6)
C3	0.0414 (8)	0.0372 (8)	0.0350 (8)	−0.0021 (6)	0.0002 (6)	−0.0034 (6)
C4	0.0311 (7)	0.0354 (8)	0.0291 (7)	−0.0033 (6)	0.0016 (6)	−0.0006 (6)
C5	0.0405 (8)	0.0314 (8)	0.0344 (7)	0.0001 (6)	−0.0011 (6)	0.0009 (6)
C6	0.0354 (8)	0.0407 (8)	0.0297 (7)	−0.0013 (6)	−0.0037 (6)	0.0029 (6)
C7	0.0437 (8)	0.0379 (9)	0.0312 (7)	−0.0045 (6)	−0.0047 (6)	−0.0053 (6)
C8	0.0412 (8)	0.0318 (8)	0.0370 (8)	−0.0010 (6)	−0.0011 (6)	−0.0003 (6)
C9	0.0344 (8)	0.0364 (8)	0.0301 (7)	−0.0011 (6)	−0.0005 (6)	0.0019 (6)
C10	0.0436 (9)	0.0422 (9)	0.0339 (8)	0.0007 (7)	−0.0030 (6)	0.0033 (6)

O1—C10	1.3626 (18)	C3—C4	1.4457 (19)
O1—C2	1.3951 (19)	C3—H3A	0.9300
O2—C10	1.2370 (18)	C4—C5	1.3813 (19)
O3—C8	1.3553 (18)	C4—C9	1.417 (2)
O3—H3	0.8200	C5—C6	1.394 (2)
O4—C6	1.3518 (17)	C5—H5	0.9300
O4—H4	0.8200	C6—C7	1.393 (2)
C1—C2	1.493 (2)	C7—C8	1.378 (2)
C1—H1A	0.9600	C7—H7	0.9300
C1—H1B	0.9600	C8—C9	1.418 (2)
C1—H1C	0.9600	C9—C10	1.426 (2)
C2—C3	1.325 (2)
C10—O1—C2	121.61 (11)	C4—C5—C6	119.64 (13)
C8—O3—H3	109.5	C4—C5—H5	120.2
C6—O4—H4	109.5	C6—C5—H5	120.2
C2—C1—H1A	109.5	O4—C6—C7	122.43 (13)
C2—C1—H1B	109.5	O4—C6—C5	116.35 (13)
H1A—C1—H1B	109.5	C7—C6—C5	121.22 (13)
C2—C1—H1C	109.5	C8—C7—C6	119.81 (13)
H1A—C1—H1C	109.5	C8—C7—H7	120.1
H1B—C1—H1C	109.5	C6—C7—H7	120.1
C3—C2—O1	120.81 (13)	O3—C8—C7	118.69 (13)
C3—C2—C1	128.92 (15)	O3—C8—C9	121.23 (13)
O1—C2—C1	110.27 (13)	C7—C8—C9	120.08 (13)
C2—C3—C4	121.57 (14)	C4—C9—C8	119.18 (12)
C2—C3—H3A	119.2	C4—C9—C10	120.08 (13)
C4—C3—H3A	119.2	C8—C9—C10	120.74 (13)
C5—C4—C9	120.07 (12)	O2—C10—O1	115.39 (13)
C5—C4—C3	122.96 (13)	O2—C10—C9	125.66 (14)
C9—C4—C3	116.96 (12)	O1—C10—C9	118.96 (13)
C10—O1—C2—C3	0.1 (2)	C5—C4—C9—C8	0.3 (2)
C10—O1—C2—C1	179.78 (13)	C3—C4—C9—C8	−179.69 (13)
O1—C2—C3—C4	−0.1 (2)	C5—C4—C9—C10	179.32 (13)
C1—C2—C3—C4	−179.74 (14)	C3—C4—C9—C10	−0.66 (19)
C2—C3—C4—C5	−179.60 (14)	O3—C8—C9—C4	−179.69 (13)
C2—C3—C4—C9	0.4 (2)	C7—C8—C9—C4	0.5 (2)
C9—C4—C5—C6	−1.1 (2)	O3—C8—C9—C10	1.3 (2)
C3—C4—C5—C6	178.85 (13)	C7—C8—C9—C10	−178.57 (13)
C4—C5—C6—O4	−178.42 (12)	C2—O1—C10—O2	179.49 (13)
C4—C5—C6—C7	1.3 (2)	C2—O1—C10—C9	−0.4 (2)
O4—C6—C7—C8	179.14 (14)	C4—C9—C10—O2	−179.17 (15)
C5—C6—C7—C8	−0.5 (2)	C8—C9—C10—O2	−0.2 (2)
C6—C7—C8—O3	179.79 (14)	C4—C9—C10—O1	0.7 (2)
C6—C7—C8—C9	−0.3 (2)	C8—C9—C10—O1	179.67 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.92	2.6426 (16)	146
O4—H4···O2i	0.82	1.96	2.7225 (15)	155
C5—H5···O4ii	0.93	2.60	3.4659 (19)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O2i	0.82	1.96	2.7225 (15)	155
C5—H5⋯O4ii	0.93	2.60	3.4659 (19)	155

Symmetry codes: (i) ; (ii) .