(6S*)-6-[(1S*,2R*)-1,2-Di­hydroxy­pent­yl]-4-meth­oxy-5,6-di­hydro-2H-pyran-2-one

Valenti, D.J.; Arif, A.M.; Strobel, G.A.; Harper, J.K.

doi:10.1107/S1600536813027025

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Pages o1657-o1658

doi:10.1107/S1600536813027025

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(6S)-6-[(1S,2R*)-1,2-Dihydroxypentyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one

Domenic J. Valenti,^a Atta M. Arif,^b Gary A. Strobel ^c and James K. Harper ^a ^*

^aDepartment of Chemistry, University of Central Florida, 4104 Libra Drive, Orlando, FL 32816, USA, ^bUniversity of Utah, Department of Chemistry, 315 S. 1400 E. Rm. 2020, Salt Lake City, UT 84112, USA, and ^cDepartment of Plant Sciences and Plant Pathology, Montana State University, 206 Plant Bioscience Building, Bozeman, MT 59717, USA
^*Correspondence e-mail: James.Harper@ucf.edu

(Received 11 September 2013; accepted 1 October 2013; online 19 October 2013)

The title compound, C₁₁H₁₈O₅, was isolated from a liquid culture of Pestalotiopsis sp. In the molecule, 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, molecules are linked via O—H⋯O hydrogen bonds forming a three-dimensional network.

CCDC reference: 964216

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_r = 230.25
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.052
wR(F²) = 0.121
S = 1.06
1616 reflections
188 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ .

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.

Supporting information

CCDC reference: 964216

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813027025/lh5653sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813027025/lh5653Isup3.cml

checkCIF report

Comment top

The title compound was first isolated from an unidentified Penicillium sp. (McGahren et al., 1973). Multiple routes have been reported for the total synthesis (Kirihata et al., 1990; Kirihata et al., 1992a; Masaki et al., 1994) including syntheses creating unnatral stereoisomers (Kirihata et al., 1992b). Closely related products have been reported from other fungi (Kirihata et al., 1996; Lee et al., 1995). The 6-substituted 5,6-dihydropyran-2-one moiety present in the title compound is also found in natural products from several species of plants and fungi (Davies-Coleman & Rivett, 1989). Although many structures with this moiety exhibit bioactivity, it appears that the title compound displays none of the reported activities. Notably, the gibberellin synergistic activity of the very closely related compound pestalotin is not found (Kimura et al., 1986; Venkatasubbaiah & Van Dyke, 1991). In our lab we observed moderate antifungal activity. Crystal structures for the related natural products, kavain, dihydrokavain and methysticin have been reported (Yoshino & Nowacki, 1972; Engel & Nowacki, 1972a; Engel & Nowacki, 1972b). In the title compound, the atoms of the pyran-2-one assume a half-chair conformation. The conformations of the methoxy and dihydroxypentyl groups are shown in Fig. 1. Carbons 4' and 5' are disordered over two sites with occupancies of 0.881 (10):0.119 (10). In the crystal, molecules are linked via O—H···O hydrogen bonds forming a three-dimensional network (see Table 1 and Fig. 2).

Related literature top

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 top

The title compound was obtained by liquid-liquid extraction (CH₂Cl₂/H₂O) of a culture of an endophytic Pestalotiopsis sp. The CH₂Cl₂ fraction was evaporated under reduced pressure then purified by chromatography on a silica column with CHCl₃/CH₃OH (8/2) as eluent. After pooling common fractions, a crystal was grown by slow evaporation of a MeOH solution.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are shown at the 50% probability level on non-hydrogen atoms. The disorder is not shown.
	Fig. 2. A portion of the crystal structure viewed along the a axis. The dashed lines indicate O—H···O hydrogen bonds. The disorder is not shown.

(6S*)-6-[(1S*,2R*)-1,2-Dihydroxypentyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one top

Crystal data top

C₁₁H₁₈O₅	F(000) = 496
M_r = 230.25	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0544P)² + 0.1236P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
1616 reflections	Δρ_max = 0.16 e Å⁻³
188 parameters	Δρ_min = −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)

Crystal data top

C₁₁H₁₈O₅	V = 1200.02 (19) Å³
M_r = 230.25	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.0375 (3) Å	µ = 0.10 mm⁻¹
b = 11.4515 (13) Å	T = 200 K
c = 20.802 (2) Å	0.28 × 0.18 × 0.08 mm

Data collection top

Nonius KappaCCD diffractometer	1616 independent reflections
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	1153 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.992	R_int = 0.043
2711 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.16 e Å⁻³
1616 reflections	Δρ_min = −0.18 e Å⁻³
188 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+3/2; (ii) x−1/2, −y+1/2, −z+2.

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+3/2; (ii) x−1/2, −y+1/2, −z+2.

References

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Volume 69| Part 11| November 2013| Pages o1657-o1658

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(6S*)-6-[(1S*,2R*)-1,2-Di­hy­droxy­pent­yl]-4-meth­­oxy-5,6-di­hydro-2H-pyran-2-one

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organic compounds

(6S)-6-[(1S,2R*)-1,2-Dihydroxypentyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one