(6S*)-6-[(1S*,2R*)-1,2-Di-hydroxy-pent-yl]-4-meth-oxy-5,6-di-hydro-2H-pyran-2-one.

The title compound, C11H18O5, was isolated from a liquid culture of Pestalotiopsis sp. In the mol-ecule, the pyran-2-one ring assumes a half-chair conformation. The two terminal C atoms of the pentyl group were refined as disordered over two sets of sites, with refined occupancies of 0.881 (10) and 0.119 (10). In the crystal, mol-ecules are linked via O-H⋯O hydrogen bonds forming a three-dimensional network.

Related literature

For the first isolation of the title compound, see: McGahren et al. (1973 ▶). For the natural and unnatural stereospecific synthesis, see: Kirihata et al. (1990 ▶, 1992a ▶,b ▶); Masaki et al. (1994 ▶). For closely related products from other fungi, see: Kimura et al. (1986 ▶); Kirihata et al. (1996 ▶); Lee et al. (1995 ▶); Davies-Coleman & Rivett (1989 ▶). For biological activity, see: Venkatasubbaiah & Van Dyke (1991 ▶). For crystal structures of related compounds, see: Yoshino & Nowacki (1972 ▶); Engel & Nowacki (1972a ▶,b ▶).

Experimental

Crystal data

C11H18O5

M = 230.25

Orthorhombic,

a = 5.0375 (3) Å

b = 11.4515 (13) Å

c = 20.802 (2) Å

V = 1200.02 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 200 K

0.28 × 0.18 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997 ▶) T min = 0.973, T max = 0.992

2711 measured reflections

1616 independent reflections

1153 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.121

S = 1.06

1616 reflections

188 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.18 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, 2008 ▶); molecular graphics: WinGX (Farrugia, 2012 ▶), ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813027025/lh5653sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813027025/lh5653Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813027025/lh5653Isup3.cml

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

C11H18O5	F(000) = 496
Mr = 230.25	Dx = 1.274 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 17230 reflections
a = 5.0375 (3) Å	θ = 1.0–27.5°
b = 11.4515 (13) Å	µ = 0.10 mm−1
c = 20.802 (2) Å	T = 200 K
V = 1200.02 (19) Å3	Plate, colorless
Z = 4	0.28 × 0.18 × 0.08 mm

Nonius KappaCCD diffractometer	1616 independent reflections
Radiation source: fine-focus sealed tube	1153 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ plus ω scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −6→6
Tmin = 0.973, Tmax = 0.992	k = −14→14
2711 measured reflections	l = −26→26

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)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121	w = 1/[σ2(Fo2) + (0.0544P)2 + 0.1236P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1616 reflections	Δρmax = 0.16 e Å−3
188 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.033 (6)

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm that effectively corrects for absorption effects. High redundancy data were used in the scaling program thus the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97<i/> input file.

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	Occ. (<1)
O1	0.4082 (4)	0.31378 (17)	0.78556 (9)	0.0429 (5)
O2	0.5372 (5)	0.4250 (2)	0.70604 (12)	0.0678 (7)
O4	−0.0742 (6)	0.5734 (2)	0.85714 (11)	0.0685 (8)
O1'	0.5361 (4)	0.1294 (2)	0.86362 (10)	0.0451 (6)
H1'O	0.516 (7)	0.066 (3)	0.8434 (15)	0.050 (10)*
O2'	0.2491 (5)	0.21272 (19)	0.97762 (9)	0.0443 (5)
H2'O	0.125 (8)	0.238 (3)	0.9970 (17)	0.051 (10)*
C2	0.4146 (7)	0.4194 (3)	0.75666 (15)	0.0481 (8)
C3	0.2702 (8)	0.5156 (3)	0.78511 (15)	0.0541 (8)
H3	0.302 (8)	0.590 (3)	0.7637 (17)	0.070 (11)*
C4	0.0890 (7)	0.4946 (3)	0.83017 (13)	0.0520 (8)
C5	0.0460 (6)	0.3748 (3)	0.85552 (15)	0.0454 (7)
H5A	−0.004 (7)	0.381 (2)	0.9013 (15)	0.048 (8)*
H5B	−0.094 (8)	0.335 (3)	0.8314 (15)	0.056 (9)*
C6	0.3007 (6)	0.3053 (3)	0.85045 (13)	0.0395 (7)
H6	0.433 (6)	0.340 (2)	0.8789 (12)	0.028 (6)*
C1'	0.2742 (5)	0.1766 (3)	0.86336 (14)	0.0376 (6)
H1'	0.168 (5)	0.146 (2)	0.8299 (12)	0.026 (7)*
C2'	0.1275 (6)	0.1490 (3)	0.92562 (14)	0.0421 (7)
H2'	−0.057 (6)	0.174 (3)	0.9211 (14)	0.044 (8)*
C3'A	0.1175 (9)	0.0209 (3)	0.94034 (14)	0.0598 (9)	0.881 (10)
H3'A	0.3000	−0.0079	0.9481	0.072*	0.881 (10)
H3'B	0.0454	−0.0213	0.9027	0.072*	0.881 (10)
C4'A	−0.0549 (13)	−0.0058 (5)	0.99940 (18)	0.0624 (14)	0.881 (10)
H4'A	0.0249	0.0315	1.0377	0.075*	0.881 (10)
H4'B	−0.2335	0.0283	0.9930	0.075*	0.881 (10)
C5'A	−0.0814 (18)	−0.1325 (4)	1.0111 (3)	0.118 (3)	0.881 (10)
H5'A	−0.1905	−0.1454	1.0495	0.177*	0.881 (10)
H5'B	0.0949	−0.1666	1.0178	0.177*	0.881 (10)
H5'C	−0.1660	−0.1695	0.9739	0.177*	0.881 (10)
C3'B	0.1175 (9)	0.0209 (3)	0.94034 (14)	0.0598 (9)	0.119 (10)
H3'C	0.2915	−0.0094	0.9258	0.072*	0.119 (10)
H3'D	−0.0147	−0.0109	0.9098	0.072*	0.119 (10)
C4'B	0.064 (7)	−0.043 (3)	1.0025 (13)	0.036 (7)*	0.119 (10)
H4'C	0.1133	0.0035	1.0409	0.043*	0.119 (10)
H4'D	0.1484	−0.1207	1.0041	0.043*	0.119 (10)
C5'B	−0.244 (5)	−0.049 (2)	0.9920 (11)	0.038 (8)*	0.119 (10)
H5'D	−0.3267	−0.0887	1.0287	0.057*	0.119 (10)
H5'E	−0.2819	−0.0932	0.9526	0.057*	0.119 (10)
H5'F	−0.3161	0.0299	0.9881	0.057*	0.119 (10)
C7	−0.0519 (12)	0.6930 (3)	0.83475 (18)	0.0924 (17)
H7A	−0.1803	0.7420	0.8577	0.139*
H7B	−0.0884	0.6960	0.7885	0.139*
H7C	0.1282	0.7218	0.8430	0.139*

	U11	U22	U33	U12	U13	U23
O1	0.0439 (11)	0.0449 (12)	0.0398 (10)	−0.0023 (9)	0.0045 (9)	0.0010 (9)
O2	0.0802 (18)	0.0588 (15)	0.0645 (14)	0.0010 (13)	0.0250 (14)	0.0148 (12)
O4	0.0831 (18)	0.0673 (15)	0.0549 (13)	0.0342 (14)	−0.0025 (13)	−0.0027 (11)
O1'	0.0373 (11)	0.0457 (13)	0.0525 (12)	0.0014 (9)	0.0025 (9)	−0.0052 (11)
O2'	0.0365 (11)	0.0575 (13)	0.0388 (10)	−0.0012 (11)	−0.0009 (9)	−0.0102 (9)
C2	0.0505 (18)	0.0443 (17)	0.0497 (17)	−0.0040 (15)	−0.0004 (15)	0.0035 (15)
C3	0.071 (2)	0.0453 (19)	0.0460 (17)	0.0060 (18)	−0.0063 (16)	0.0010 (16)
C4	0.057 (2)	0.058 (2)	0.0406 (15)	0.0203 (18)	−0.0105 (15)	−0.0035 (15)
C5	0.0386 (16)	0.0567 (19)	0.0408 (16)	0.0048 (14)	0.0013 (13)	−0.0036 (14)
C6	0.0356 (14)	0.0472 (17)	0.0356 (14)	−0.0013 (12)	−0.0022 (11)	−0.0066 (12)
C1'	0.0315 (13)	0.0438 (16)	0.0375 (14)	−0.0017 (12)	−0.0029 (12)	−0.0064 (13)
C2'	0.0328 (15)	0.0548 (19)	0.0388 (15)	−0.0060 (13)	−0.0019 (12)	−0.0054 (14)
C3'A	0.078 (2)	0.053 (2)	0.0477 (17)	−0.0177 (19)	0.0093 (16)	−0.0044 (16)
C4'A	0.077 (4)	0.058 (3)	0.053 (2)	−0.004 (3)	0.016 (2)	0.002 (2)
C5'A	0.197 (8)	0.061 (3)	0.097 (4)	−0.029 (4)	0.070 (5)	0.002 (3)
C7	0.152 (5)	0.067 (3)	0.059 (2)	0.053 (3)	−0.006 (3)	0.0042 (19)

O1—C2	1.351 (3)	C2'—C3'A	1.499 (5)
O1—C6	1.458 (3)	C2'—H2'	0.98 (3)
O2—C2	1.222 (4)	C3'A—C4'A	1.536 (5)
O4—C4	1.343 (4)	C3'A—H3'A	0.9900
O4—C7	1.451 (4)	C3'A—H3'B	0.9900
O1'—C1'	1.426 (3)	C4'A—C5'A	1.477 (7)
O1'—H1'O	0.85 (3)	C4'A—H4'A	0.9900
O2'—C2'	1.442 (3)	C4'A—H4'B	0.9900
O2'—H2'O	0.80 (4)	C5'A—H5'A	0.9800
C2—C3	1.447 (5)	C5'A—H5'B	0.9800
C3—C4	1.330 (5)	C5'A—H5'C	0.9800
C3—H3	0.98 (4)	C4'B—C5'B	1.57 (4)
C4—C5	1.486 (5)	C4'B—H4'C	0.9900
C5—C6	1.513 (4)	C4'B—H4'D	0.9900
C5—H5A	0.99 (3)	C5'B—H5'D	0.9800
C5—H5B	0.97 (4)	C5'B—H5'E	0.9800
C6—C1'	1.504 (4)	C5'B—H5'F	0.9800
C6—H6	0.98 (3)	C7—H7A	0.9800
C1'—C2'	1.524 (4)	C7—H7B	0.9800
C1'—H1'	0.94 (3)	C7—H7C	0.9800
C2—O1—C6	118.7 (2)	C3'A—C2'—H2'	105.9 (18)
C4—O4—C7	116.9 (3)	C1'—C2'—H2'	108.6 (17)
C1'—O1'—H1'O	102 (3)	C2'—C3'A—C4'A	112.2 (3)
C2'—O2'—H2'O	103 (3)	C2'—C3'A—H3'A	109.2
O2—C2—O1	116.3 (3)	C4'A—C3'A—H3'A	109.2
O2—C2—C3	124.5 (3)	C2'—C3'A—H3'B	109.2
O1—C2—C3	119.2 (3)	C4'A—C3'A—H3'B	109.2
C4—C3—C2	119.7 (3)	H3'A—C3'A—H3'B	107.9
C4—C3—H3	126 (2)	C5'A—C4'A—C3'A	112.3 (4)
C2—C3—H3	113 (2)	C5'A—C4'A—H4'A	109.1
C3—C4—O4	126.4 (3)	C3'A—C4'A—H4'A	109.1
C3—C4—C5	121.1 (3)	C5'A—C4'A—H4'B	109.1
O4—C4—C5	112.5 (3)	C3'A—C4'A—H4'B	109.1
C4—C5—C6	109.7 (3)	H4'A—C4'A—H4'B	107.9
C4—C5—H5A	108.2 (17)	C4'A—C5'A—H5'A	109.5
C6—C5—H5A	108.9 (19)	C4'A—C5'A—H5'B	109.5
C4—C5—H5B	110.5 (19)	H5'A—C5'A—H5'B	109.5
C6—C5—H5B	109 (2)	C4'A—C5'A—H5'C	109.5
H5A—C5—H5B	110 (3)	H5'A—C5'A—H5'C	109.5
O1—C6—C1'	105.3 (2)	H5'B—C5'A—H5'C	109.5
O1—C6—C5	110.2 (2)	C5'B—C4'B—H4'C	112.8
C1'—C6—C5	115.3 (2)	C5'B—C4'B—H4'D	112.8
O1—C6—H6	106.3 (15)	H4'C—C4'B—H4'D	110.3
C1'—C6—H6	110.7 (15)	C4'B—C5'B—H5'D	109.5
C5—C6—H6	108.7 (15)	C4'B—C5'B—H5'E	109.5
O1'—C1'—C6	106.9 (2)	H5'D—C5'B—H5'E	109.5
O1'—C1'—C2'	111.5 (2)	C4'B—C5'B—H5'F	109.5
C6—C1'—C2'	113.4 (2)	H5'D—C5'B—H5'F	109.5
O1'—C1'—H1'	112.6 (16)	H5'E—C5'B—H5'F	109.5
C6—C1'—H1'	106.5 (15)	O4—C7—H7A	109.5
C2'—C1'—H1'	106.0 (16)	O4—C7—H7B	109.5
O2'—C2'—C3'A	110.9 (3)	H7A—C7—H7B	109.5
O2'—C2'—C1'	109.1 (2)	O4—C7—H7C	109.5
C3'A—C2'—C1'	113.1 (3)	H7A—C7—H7C	109.5
O2'—C2'—H2'	109.1 (18)	H7B—C7—H7C	109.5
C6—O1—C2—O2	170.8 (3)	C4—C5—C6—C1'	−169.6 (2)
C6—O1—C2—C3	−11.9 (4)	O1—C6—C1'—O1'	64.9 (3)
O2—C2—C3—C4	162.4 (3)	C5—C6—C1'—O1'	−173.5 (2)
O1—C2—C3—C4	−14.7 (5)	O1—C6—C1'—C2'	−171.8 (2)
C2—C3—C4—O4	−174.4 (3)	C5—C6—C1'—C2'	−50.2 (3)
C2—C3—C4—C5	4.7 (5)	O1'—C1'—C2'—O2'	68.4 (3)
C7—O4—C4—C3	0.3 (5)	C6—C1'—C2'—O2'	−52.4 (3)
C7—O4—C4—C5	−178.8 (3)	O1'—C1'—C2'—C3'A	−55.5 (3)
C3—C4—C5—C6	28.2 (4)	C6—C1'—C2'—C3'A	−176.2 (3)
O4—C4—C5—C6	−152.6 (3)	O2'—C2'—C3'A—C4'A	63.0 (4)
C2—O1—C6—C1'	169.7 (2)	C1'—C2'—C3'A—C4'A	−174.2 (3)
C2—O1—C6—C5	44.8 (3)	C2'—C3'A—C4'A—C5'A	175.7 (5)
C4—C5—C6—O1	−50.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1′—H1′O···O2i	0.85 (3)	1.93 (3)	2.778 (3)	177 (3)
O2′—H2′O···O2′ii	0.80 (4)	2.05 (4)	2.8178 (18)	163 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1′—H1′O⋯O2i	0.85 (3)	1.93 (3)	2.778 (3)	177 (3)
O2′—H2′O⋯O2′ii	0.80 (4)	2.05 (4)	2.8178 (18)	163 (4)

Symmetry codes: (i) ; (ii) .