Alternariol.

IN THE TITLE COMPOUND (SYSTEMATIC NAME: 3,7,9-trihydr-oxy-1-methyl-6H-benzo[c]chromen-6-one), C(14)H(10)O(5), the methyl group is shifted out of the molecular plane due to a steric collision, thus causing a slight twist of the benzene rings. The mol-ecular structure is stabilized by an intra-molecular O-H⋯O hydrogen bond, generating an S(6) ring. In the crystal, mol-ecules are connected by inter-molecular O-H⋯O hydrogen bonds into a three-dimensional network.

Related literature

Alternariol is a mycotoxin (toxic secondary fungal metabolite) produced by ubiquitous Alternaria moulds. For information on occurence and toxicity, see: Weidenbörner (2001 ▶); Brugger et al. (2006 ▶); Wollenhaupt et al. (2008 ▶); Fehr et al. (2009 ▶). For crystallization, alternariol was obtained by total synthesis according to Koch et al. (2005 ▶). For a comparable structure, (2-chloro-7-hydr­oxy-8-methyl-6H-benzo[c]chromen-6-one), see: Appel et al. (2006 ▶).

Experimental

Crystal data

C14H10O5

M = 258.22

Orthorhombic,

a = 18.969 (3) Å

b = 3.7244 (6) Å

c = 15.235 (3) Å

V = 1076.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 150 K

0.40 × 0.10 × 0.02 mm

Data collection

Stoe IPDS diffractometer

6072 measured reflections

1338 independent reflections

1053 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.069

S = 0.99

1338 reflections

191 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.23 e Å−3

Data collection: X-AREA (Stoe & Cie, 2006 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2010 ▶) and ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810017502/bt5266sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017502/bt5266Isup2.hkl

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

C14H10O5	F(000) = 536
Mr = 258.22	Dx = 1.594 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1894 reflections
a = 18.969 (3) Å	θ = 5–26°
b = 3.7244 (6) Å	µ = 0.12 mm−1
c = 15.235 (3) Å	T = 150 K
V = 1076.3 (3) Å3	Needle, colourless
Z = 4	0.40 × 0.10 × 0.02 mm

Stoe IPDS diffractometer	1053 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.067
graphite	θmax = 28.1°, θmin = 2.5°
rotation method scans	h = −24→22
6072 measured reflections	k = −4→4
1338 independent reflections	l = −20→20

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ2(Fo2) + (0.0314P)2] where P = (Fo2 + 2Fc2)/3
1338 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.23 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.54295 (9)	0.3728 (6)	0.78417 (11)	0.0213 (4)
O2	0.44464 (9)	0.1215 (6)	0.74006 (11)	0.0272 (5)
O3	0.42666 (9)	−0.0612 (6)	0.57652 (13)	0.0277 (5)
H3	0.4192 (17)	−0.038 (10)	0.632 (2)	0.033*
O4	0.61983 (10)	0.1209 (7)	0.38531 (11)	0.0275 (5)
H4	0.5946 (18)	0.002 (10)	0.344 (2)	0.033*
O5	0.74389 (10)	0.8553 (6)	0.91670 (10)	0.0260 (5)
H5	0.7843	0.9307	0.9038	0.031*
C1	0.50516 (13)	0.2203 (8)	0.71956 (16)	0.0193 (6)
C2	0.53589 (13)	0.1856 (8)	0.63425 (15)	0.0167 (6)
C3	0.49365 (13)	0.0493 (8)	0.56447 (16)	0.0192 (6)
C4	0.52045 (14)	0.0246 (8)	0.48049 (17)	0.0194 (6)
H4A	0.4917 (15)	−0.072 (8)	0.4295 (19)	0.023*
C5	0.58935 (13)	0.1357 (9)	0.46651 (15)	0.0183 (6)
C6	0.63205 (15)	0.2688 (8)	0.53304 (15)	0.0178 (6)
H6A	0.6788 (15)	0.341 (8)	0.5183 (18)	0.021*
C7	0.60688 (12)	0.2911 (7)	0.61830 (15)	0.0135 (5)
C8	0.64850 (13)	0.4228 (7)	0.69286 (14)	0.0141 (5)
C9	0.61339 (12)	0.4710 (8)	0.77287 (16)	0.0166 (6)
C10	0.64335 (14)	0.6136 (8)	0.84775 (16)	0.0194 (6)
H10	0.6189 (14)	0.644 (8)	0.9006 (18)	0.023*
C11	0.71326 (13)	0.7093 (8)	0.84418 (16)	0.0186 (6)
C12	0.75199 (13)	0.6479 (8)	0.76803 (16)	0.0159 (5)
H12	0.7968 (16)	0.696 (8)	0.7685 (17)	0.019*
C13	0.72187 (13)	0.5072 (7)	0.69300 (15)	0.0146 (5)
C14	0.77182 (13)	0.4380 (8)	0.61791 (16)	0.0198 (6)
H14A	0.8205	0.4683	0.6382	0.030*
H14B	0.7622	0.6083	0.5704	0.030*
H14C	0.7652	0.1923	0.5964	0.030*

	U11	U22	U33	U12	U13	U23
O1	0.0154 (8)	0.0343 (13)	0.0141 (8)	−0.0028 (8)	0.0031 (6)	−0.0013 (9)
O2	0.0164 (9)	0.0475 (14)	0.0177 (8)	−0.0068 (9)	0.0028 (7)	0.0060 (9)
O3	0.0125 (9)	0.0439 (14)	0.0268 (10)	−0.0096 (9)	0.0011 (8)	−0.0021 (11)
O4	0.0164 (9)	0.0518 (15)	0.0143 (9)	−0.0034 (10)	−0.0002 (7)	−0.0092 (9)
O5	0.0244 (10)	0.0405 (13)	0.0131 (8)	−0.0053 (9)	−0.0034 (7)	−0.0063 (9)
C1	0.0152 (13)	0.0243 (18)	0.0183 (13)	−0.0006 (11)	−0.0013 (9)	0.0027 (11)
C2	0.0139 (12)	0.0187 (16)	0.0176 (12)	0.0002 (10)	0.0010 (9)	0.0038 (11)
C3	0.0113 (12)	0.0239 (17)	0.0222 (13)	−0.0027 (11)	−0.0021 (10)	0.0012 (12)
C4	0.0166 (13)	0.0218 (17)	0.0200 (12)	0.0027 (11)	−0.0052 (10)	−0.0022 (11)
C5	0.0149 (13)	0.0277 (17)	0.0123 (11)	0.0025 (12)	0.0021 (9)	−0.0019 (12)
C6	0.0134 (12)	0.0226 (17)	0.0175 (12)	0.0001 (10)	0.0012 (9)	−0.0003 (11)
C7	0.0124 (11)	0.0153 (15)	0.0127 (11)	0.0024 (9)	0.0007 (9)	0.0026 (11)
C8	0.0170 (12)	0.0150 (14)	0.0102 (10)	0.0036 (10)	−0.0006 (9)	−0.0001 (10)
C9	0.0129 (11)	0.0216 (17)	0.0153 (10)	0.0008 (10)	−0.0006 (10)	0.0035 (11)
C10	0.0207 (14)	0.0257 (17)	0.0117 (11)	0.0037 (11)	0.0030 (9)	0.0001 (11)
C11	0.0205 (13)	0.0227 (17)	0.0125 (11)	0.0014 (11)	−0.0061 (10)	−0.0013 (11)
C12	0.0124 (11)	0.0191 (15)	0.0163 (11)	0.0014 (10)	−0.0020 (9)	0.0014 (11)
C13	0.0166 (12)	0.0139 (15)	0.0133 (10)	0.0023 (10)	0.0015 (9)	0.0030 (10)
C14	0.0130 (12)	0.0279 (17)	0.0184 (11)	−0.0009 (10)	0.0004 (9)	−0.0038 (12)

O1—C1	1.343 (3)	C6—C7	1.386 (3)
O1—C9	1.396 (3)	C6—H6A	0.95 (3)
O2—C1	1.245 (3)	C7—C8	1.468 (3)
O3—C3	1.348 (3)	C8—C9	1.401 (3)
O3—H3	0.86 (3)	C8—C13	1.427 (4)
O4—C5	1.367 (3)	C9—C10	1.381 (4)
O4—H4	0.91 (4)	C10—C11	1.374 (4)
O5—C11	1.362 (3)	C10—H10	0.94 (3)
O5—H5	0.8400	C11—C12	1.392 (4)
C1—C2	1.430 (3)	C12—C13	1.381 (4)
C2—C7	1.424 (3)	C12—H12	0.87 (3)
C2—C3	1.425 (4)	C13—C14	1.508 (3)
C3—C4	1.380 (3)	C14—H14A	0.9800
C4—C5	1.387 (4)	C14—H14B	0.9800
C4—H4A	1.01 (3)	C14—H14C	0.9800
C5—C6	1.389 (4)
C1—O1—C9	122.07 (19)	C9—C8—C13	115.7 (2)
C3—O3—H3	105 (2)	C9—C8—C7	117.4 (2)
C5—O4—H4	115 (2)	C13—C8—C7	126.8 (2)
C11—O5—H5	109.5	C10—C9—O1	113.1 (2)
O2—C1—O1	115.6 (2)	C10—C9—C8	124.9 (2)
O2—C1—C2	125.2 (2)	O1—C9—C8	121.9 (2)
O1—C1—C2	119.1 (2)	C11—C10—C9	117.7 (2)
C7—C2—C3	120.2 (2)	C11—C10—H10	118.7 (17)
C7—C2—C1	121.0 (2)	C9—C10—H10	123.6 (17)
C3—C2—C1	118.8 (2)	O5—C11—C10	118.9 (2)
O3—C3—C4	116.9 (2)	O5—C11—C12	121.1 (2)
O3—C3—C2	122.5 (2)	C10—C11—C12	120.0 (2)
C4—C3—C2	120.6 (2)	C13—C12—C11	122.2 (2)
C3—C4—C5	118.0 (2)	C13—C12—H12	119.3 (18)
C3—C4—H4A	122.4 (16)	C11—C12—H12	118.4 (18)
C5—C4—H4A	119.6 (16)	C12—C13—C8	119.2 (2)
O4—C5—C4	121.7 (2)	C12—C13—C14	115.6 (2)
O4—C5—C6	115.4 (2)	C8—C13—C14	125.1 (2)
C4—C5—C6	122.9 (2)	C13—C14—H14A	109.5
C7—C6—C5	120.3 (2)	C13—C14—H14B	109.5
C7—C6—H6A	121.6 (17)	H14A—C14—H14B	109.5
C5—C6—H6A	118.1 (17)	C13—C14—H14C	109.5
C6—C7—C2	118.0 (2)	H14A—C14—H14C	109.5
C6—C7—C8	124.1 (2)	H14B—C14—H14C	109.5
C2—C7—C8	118.0 (2)
C9—O1—C1—O2	174.9 (2)	C6—C7—C8—C9	172.4 (3)
C9—O1—C1—C2	−5.6 (4)	C2—C7—C8—C9	−6.5 (4)
O2—C1—C2—C7	−176.9 (3)	C6—C7—C8—C13	−7.9 (4)
O1—C1—C2—C7	3.6 (4)	C2—C7—C8—C13	173.3 (3)
O2—C1—C2—C3	4.3 (4)	C1—O1—C9—C10	−178.2 (3)
O1—C1—C2—C3	−175.2 (3)	C1—O1—C9—C8	1.3 (4)
C7—C2—C3—O3	178.6 (3)	C13—C8—C9—C10	4.5 (4)
C1—C2—C3—O3	−2.6 (4)	C7—C8—C9—C10	−175.7 (3)
C7—C2—C3—C4	−1.3 (4)	C13—C8—C9—O1	−174.9 (2)
C1—C2—C3—C4	177.5 (3)	C7—C8—C9—O1	4.8 (4)
O3—C3—C4—C5	−179.8 (3)	O1—C9—C10—C11	178.2 (3)
C2—C3—C4—C5	0.1 (4)	C8—C9—C10—C11	−1.3 (4)
C3—C4—C5—O4	−179.9 (3)	C9—C10—C11—O5	179.1 (2)
C3—C4—C5—C6	0.1 (5)	C9—C10—C11—C12	−2.6 (4)
O4—C5—C6—C7	−179.1 (3)	O5—C11—C12—C13	−178.6 (3)
C4—C5—C6—C7	0.9 (5)	C10—C11—C12—C13	3.1 (4)
C5—C6—C7—C2	−2.1 (4)	C11—C12—C13—C8	0.3 (4)
C5—C6—C7—C8	179.1 (3)	C11—C12—C13—C14	−176.7 (3)
C3—C2—C7—C6	2.3 (4)	C9—C8—C13—C12	−3.9 (4)
C1—C2—C7—C6	−176.5 (3)	C7—C8—C13—C12	176.4 (3)
C3—C2—C7—C8	−178.8 (3)	C9—C8—C13—C14	172.9 (3)
C1—C2—C7—C8	2.5 (4)	C7—C8—C13—C14	−6.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.86 (3)	1.82 (3)	2.605 (3)	152 (3)
O4—H4···O2i	0.91 (3)	1.81 (3)	2.685 (3)	162 (3)
O5—H5···O4ii	0.84	1.97	2.809 (2)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.86 (3)	1.82 (3)	2.605 (3)	152 (3)
O4—H4⋯O2i	0.91 (3)	1.81 (3)	2.685 (3)	162 (3)
O5—H5⋯O4ii	0.84	1.97	2.809 (2)	175

Symmetry codes: (i) ; (ii) .