(4S,5S,6S)-4-Hy-droxy-3-meth-oxy-5-methyl-5,6-ep-oxy-cyclo-hex-2-en-1-one.

The title compound, C(8)H(10)O(4), was isolated from culture extracts of the endophytic fungus Xylaria sp. (PB-30). The cyclo-hexenone ring exhibits a flattened boat conformation. In the crystal structure, mol-ecules related by translation along the b axis are linked into chains through O-H⋯O hydrogen bonds. Weak non-classical C-H⋯O contacts are also observed in the structure.

Related literature

For background to the structures of bioactive secondary metabolites from endophytic fungus and their activities, see: Tansuwan et al. (2007 ▶); Shiono et al. (2005 ▶); Mitsui et al. (2004 ▶). For related structures and the assignment of the absolute configuration, see: Mitsui et al. (2004 ▶); Shiono et al. (2005 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C8H10O4

M = 170.16

Orthorhombic,

a = 4.2208 (1) Å

b = 7.5459 (3) Å

c = 25.0802 (8) Å

V = 798.80 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.42 × 0.40 × 0.30 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

6038 measured reflections

1768 independent reflections

1551 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.116

S = 1.07

1768 reflections

112 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810030850/cv2746sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030850/cv2746Isup2.hkl

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

C8H10O4	F(000) = 360
Mr = 170.16	Dx = 1.415 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2855 reflections
a = 4.2208 (1) Å	θ = 2.8–32.8°
b = 7.5459 (3) Å	µ = 0.11 mm−1
c = 25.0802 (8) Å	T = 293 K
V = 798.80 (4) Å3	Prism, colourless
Z = 4	0.42 × 0.40 × 0.30 mm

Bruker SMART APEXII CCD area-detector diffractometer	1551 reflections with I > 2σ(I)
Radiation source: Mo	Rint = 0.021
graphite	θmax = 33.1°, θmin = 2.8°
φ and ω scans	h = −6→6
6038 measured reflections	k = −11→7
1768 independent reflections	l = −37→32

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041	w = 1/[σ2(Fo2) + (0.0798P)2 + 0.0232P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.116	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.32 e Å−3
1768 reflections	Δρmin = −0.24 e Å−3
112 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.

	x	y	z	Uiso*/Ueq
C1	0.6030 (4)	0.12154 (17)	0.88766 (6)	0.0349 (3)
C2	0.6543 (4)	0.19049 (16)	0.83465 (5)	0.0337 (3)
H2	0.6778	0.1121	0.8063	0.04*
C3	0.6687 (3)	0.36664 (16)	0.82548 (5)	0.0268 (2)
C4	0.6073 (3)	0.50632 (15)	0.86741 (5)	0.0248 (2)
H4	0.3894	0.5489	0.8632	0.03*
C5	0.6459 (3)	0.43752 (15)	0.92384 (5)	0.0242 (2)
C6	0.6377 (4)	0.24623 (17)	0.93348 (5)	0.0293 (3)
H6	0.5586	0.2064	0.9682	0.035*
C7	0.5554 (5)	0.56563 (19)	0.96737 (5)	0.0372 (3)
H7A	0.678	0.6721	0.9638	0.056*
H7B	0.5964	0.5128	1.0015	0.056*
H7C	0.3342	0.5936	0.9645	0.056*
C8	0.7980 (6)	0.3240 (2)	0.73390 (6)	0.0452 (4)
H8A	0.6217	0.2477	0.7264	0.068*
H8B	0.9791	0.2537	0.7433	0.068*
H8C	0.8461	0.3938	0.7029	0.068*
O1	0.5405 (5)	−0.03468 (14)	0.89674 (5)	0.0594 (5)
O2	0.8156 (3)	0.65036 (13)	0.85837 (4)	0.0392 (3)
H2A	0.735	0.7419	0.8696	0.059*
O3	0.7187 (4)	0.43952 (13)	0.77758 (4)	0.0379 (3)
O4	0.9367 (3)	0.34098 (15)	0.93283 (4)	0.0350 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0486 (8)	0.0182 (5)	0.0379 (6)	0.0011 (5)	0.0071 (7)	−0.0006 (4)
C2	0.0484 (8)	0.0210 (5)	0.0318 (6)	−0.0004 (5)	0.0055 (6)	−0.0066 (4)
C3	0.0325 (6)	0.0226 (5)	0.0253 (5)	0.0013 (5)	0.0029 (5)	−0.0029 (4)
C4	0.0297 (5)	0.0174 (4)	0.0272 (5)	0.0020 (4)	0.0042 (4)	−0.0011 (4)
C5	0.0254 (5)	0.0211 (5)	0.0261 (5)	−0.0009 (4)	0.0018 (4)	−0.0029 (4)
C6	0.0360 (6)	0.0231 (5)	0.0289 (5)	0.0008 (5)	0.0029 (5)	0.0024 (4)
C7	0.0521 (9)	0.0286 (6)	0.0310 (6)	−0.0041 (6)	0.0082 (6)	−0.0093 (5)
C8	0.0645 (11)	0.0422 (8)	0.0290 (6)	0.0011 (9)	0.0103 (7)	−0.0080 (6)
O1	0.1057 (14)	0.0182 (4)	0.0545 (7)	−0.0065 (6)	0.0200 (9)	0.0002 (4)
O2	0.0545 (7)	0.0199 (4)	0.0431 (5)	−0.0081 (4)	0.0158 (5)	−0.0024 (4)
O3	0.0593 (7)	0.0294 (4)	0.0250 (4)	0.0029 (5)	0.0074 (5)	−0.0019 (3)
O4	0.0280 (5)	0.0368 (5)	0.0400 (5)	0.0022 (4)	−0.0047 (4)	0.0019 (4)

C1—O1	1.2292 (17)	C5—C7	1.5074 (17)
C1—C2	1.444 (2)	C6—O4	1.4506 (18)
C1—C6	1.4924 (19)	C6—H6	0.98
C2—C3	1.3503 (17)	C7—H7A	0.96
C2—H2	0.93	C7—H7B	0.96
C3—O3	1.3379 (15)	C7—H7C	0.96
C3—C4	1.5113 (16)	C8—O3	1.4393 (17)
C4—O2	1.4162 (17)	C8—H8A	0.96
C4—C5	1.5162 (17)	C8—H8B	0.96
C4—H4	0.98	C8—H8C	0.96
C5—O4	1.4448 (16)	O2—H2A	0.82
C5—C6	1.4640 (18)
O1—C1—C2	123.24 (14)	O4—C6—C5	59.43 (9)
O1—C1—C6	118.88 (14)	O4—C6—C1	112.79 (12)
C2—C1—C6	117.85 (12)	C5—C6—C1	119.79 (11)
C3—C2—C1	121.21 (11)	O4—C6—H6	117.2
C3—C2—H2	119.4	C5—C6—H6	117.2
C1—C2—H2	119.4	C1—C6—H6	117.2
O3—C3—C2	124.38 (11)	C5—C7—H7A	109.5
O3—C3—C4	111.41 (10)	C5—C7—H7B	109.5
C2—C3—C4	124.08 (11)	H7A—C7—H7B	109.5
O2—C4—C3	108.50 (10)	C5—C7—H7C	109.5
O2—C4—C5	110.21 (11)	H7A—C7—H7C	109.5
C3—C4—C5	113.09 (10)	H7B—C7—H7C	109.5
O2—C4—H4	108.3	O3—C8—H8A	109.5
C3—C4—H4	108.3	O3—C8—H8B	109.5
C5—C4—H4	108.3	H8A—C8—H8B	109.5
O4—C5—C6	59.82 (9)	O3—C8—H8C	109.5
O4—C5—C7	115.19 (12)	H8A—C8—H8C	109.5
C6—C5—C7	120.44 (11)	H8B—C8—H8C	109.5
O4—C5—C4	114.18 (10)	C4—O2—H2A	109.5
C6—C5—C4	119.29 (10)	C3—O3—C8	118.11 (11)
C7—C5—C4	115.41 (11)	C5—O4—C6	60.75 (8)
O1—C1—C2—C3	168.6 (2)	C7—C5—C6—O4	−103.26 (15)
C6—C1—C2—C3	−13.3 (3)	C4—C5—C6—O4	102.54 (13)
C1—C2—C3—O3	179.30 (16)	O4—C5—C6—C1	−100.39 (15)
C1—C2—C3—C4	−5.2 (3)	C7—C5—C6—C1	156.36 (15)
O3—C3—C4—O2	−40.34 (16)	C4—C5—C6—C1	2.2 (2)
C2—C3—C4—O2	143.68 (16)	O1—C1—C6—O4	125.98 (19)
O3—C3—C4—C5	−162.94 (13)	C2—C1—C6—O4	−52.22 (19)
C2—C3—C4—C5	21.1 (2)	O1—C1—C6—C5	−167.29 (19)
O2—C4—C5—O4	−72.54 (13)	C2—C1—C6—C5	14.5 (2)
C3—C4—C5—O4	49.10 (15)	C2—C3—O3—C8	−7.4 (3)
O2—C4—C5—C6	−140.21 (13)	C4—C3—O3—C8	176.65 (16)
C3—C4—C5—C6	−18.57 (18)	C7—C5—O4—C6	111.98 (13)
O2—C4—C5—C7	64.33 (16)	C4—C5—O4—C6	−111.05 (12)
C3—C4—C5—C7	−174.03 (13)	C1—C6—O4—C5	112.19 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1i	0.82	1.99	2.8148 (17)	180.
C4—H4···O2ii	0.98	2.54	3.521 (2)	176.
C6—H6···O4iii	0.98	2.56	3.5208 (17)	167.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1i	0.82	1.99	2.8148 (17)	180
C4—H4⋯O2ii	0.98	2.54	3.521 (2)	176
C6—H6⋯O4iii	0.98	2.56	3.5208 (17)	167

Symmetry codes: (i) ; (ii) ; (iii) .