2-C-Phenyl-erythrono-1,4-lactone.

THE TITLE COMPOUND (SYSTEMATIC NAME: 3,4-dihydr-oxy-3-phenyl-furan-2-one), C(10)H(10)O(4), features a five-membered γ-lactone ring with an envelope conformation at the C atom carrying the hydr-oxy group without the phenyl substituent. In the crystal, supra-molecular chains mediated by O-H⋯O hydrogen bonding are formed along the a-axis direction. These are consolidated in the crystal structure by C-H⋯O contacts.

Related literature

For background on the leaf-closing substance of the tropical legume Leucaena leucocephalam, see: Ueda et al. (2001 ▶); Gogoi & Argade (2004 ▶); Koumbis et al. (2006 ▶). For the synthesis of polyhydroxy­ated compounds from 1,2-dioxines, see: Robinson et al. (2006 ▶, 2009 ▶); Valente et al. (2009 ▶); Pedersen et al. (2009 ▶).

Experimental

Crystal data

C10H10O4

M = 194.18

Monoclinic,

a = 6.485 (2) Å

b = 7.324 (3) Å

c = 18.962 (7) Å

β = 99.378 (7)°

V = 888.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 173 K

0.50 × 0.20 × 0.20 mm

Data collection

Rigaku AFC12κ/SATURN724 diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.778, T max = 1.000

21683 measured reflections

1834 independent reflections

1818 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.128

S = 1.21

1834 reflections

133 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048478/sj2685sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048478/sj2685Isup2.hkl

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

C10H10O4	F(000) = 408
Mr = 194.18	Dx = 1.452 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 3641 reflections
a = 6.485 (2) Å	θ = 2.2–27.5°
b = 7.324 (3) Å	µ = 0.11 mm−1
c = 18.962 (7) Å	T = 173 K
β = 99.378 (7)°	Block, colourless
V = 888.6 (5) Å3	0.50 × 0.20 × 0.20 mm
Z = 4

Rigaku AFC12κ/SATURN724 diffractometer	1834 independent reflections
Radiation source: fine-focus sealed tube	1818 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω scans	θmax = 26.5°, θmin = 2.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→7
Tmin = 0.778, Tmax = 1.000	k = −9→9
21683 measured reflections	l = −23→23

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.21	w = 1/[σ2(Fo2) + (0.0689P)2 + 0.2568P] where P = (Fo2 + 2Fc2)/3
1834 reflections	(Δ/σ)max < 0.001
133 parameters	Δρmax = 0.28 e Å−3
2 restraints	Δρmin = −0.27 e Å−3

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
O1	−0.00052 (16)	0.88359 (15)	0.43151 (5)	0.0315 (3)
O2	−0.14194 (16)	0.60605 (17)	0.42959 (6)	0.0353 (3)
O3	0.27440 (16)	0.46977 (14)	0.44174 (5)	0.0274 (3)
H3O	0.2312	0.4653	0.4811	0.041*
O4	0.39267 (17)	0.77862 (15)	0.52318 (5)	0.0299 (3)
H4O	0.4778	0.6920	0.5321	0.045*
C2	0.0052 (2)	0.7033 (2)	0.42422 (7)	0.0260 (3)
C3	0.2212 (2)	0.64295 (18)	0.41109 (7)	0.0224 (3)
C4	0.3562 (2)	0.80116 (19)	0.44799 (7)	0.0242 (3)
H4	0.4886	0.8182	0.4282	0.029*
C5	0.2076 (2)	0.9607 (2)	0.43117 (8)	0.0292 (3)
H5A	0.2386	1.0574	0.4678	0.035*
H5B	0.2183	1.0132	0.3838	0.035*
C31	0.2337 (2)	0.63650 (18)	0.33154 (7)	0.0229 (3)
C32	0.4037 (2)	0.5486 (2)	0.31027 (8)	0.0287 (3)
H32	0.5047	0.4900	0.3448	0.034*
C33	0.4263 (3)	0.5462 (2)	0.23878 (8)	0.0336 (4)
H33	0.5412	0.4839	0.2245	0.040*
C34	0.2823 (3)	0.6341 (2)	0.18799 (8)	0.0323 (4)
H34	0.2993	0.6336	0.1392	0.039*
C35	0.1141 (3)	0.7223 (2)	0.20881 (8)	0.0313 (4)
H35	0.0155	0.7833	0.1742	0.038*
C36	0.0879 (2)	0.72227 (19)	0.28042 (8)	0.0272 (3)
H36	−0.0299	0.7811	0.2942	0.033*

	U11	U22	U33	U12	U13	U23
O1	0.0283 (6)	0.0361 (6)	0.0304 (6)	0.0074 (4)	0.0055 (4)	−0.0040 (4)
O2	0.0265 (6)	0.0529 (7)	0.0274 (5)	−0.0055 (5)	0.0068 (4)	0.0059 (5)
O3	0.0346 (6)	0.0268 (5)	0.0221 (5)	0.0030 (4)	0.0078 (4)	0.0050 (4)
O4	0.0351 (6)	0.0355 (6)	0.0185 (5)	0.0059 (4)	0.0027 (4)	−0.0025 (4)
C2	0.0261 (7)	0.0363 (8)	0.0158 (6)	0.0018 (5)	0.0039 (5)	0.0016 (5)
C3	0.0239 (7)	0.0248 (7)	0.0189 (6)	0.0020 (5)	0.0043 (5)	0.0020 (5)
C4	0.0263 (7)	0.0280 (7)	0.0187 (6)	−0.0006 (5)	0.0048 (5)	−0.0012 (5)
C5	0.0326 (8)	0.0270 (7)	0.0277 (7)	0.0011 (6)	0.0040 (6)	−0.0018 (5)
C31	0.0267 (7)	0.0230 (6)	0.0192 (6)	−0.0029 (5)	0.0048 (5)	−0.0007 (5)
C32	0.0299 (7)	0.0326 (7)	0.0242 (7)	0.0030 (6)	0.0060 (5)	0.0000 (5)
C33	0.0372 (8)	0.0382 (8)	0.0281 (7)	0.0002 (6)	0.0131 (6)	−0.0041 (6)
C34	0.0471 (9)	0.0314 (7)	0.0199 (6)	−0.0079 (6)	0.0100 (6)	−0.0030 (5)
C35	0.0417 (9)	0.0281 (7)	0.0218 (7)	−0.0011 (6)	−0.0015 (6)	0.0024 (5)
C36	0.0302 (7)	0.0273 (7)	0.0236 (7)	0.0019 (5)	0.0027 (5)	−0.0007 (5)

O1—C2	1.3286 (19)	C5—H5B	0.9900
O1—C5	1.4639 (19)	C31—C36	1.389 (2)
O2—C2	1.2085 (18)	C31—C32	1.392 (2)
O3—C3	1.4142 (16)	C32—C33	1.387 (2)
O3—H3O	0.8400	C32—H32	0.9500
O4—C4	1.4164 (16)	C33—C34	1.386 (2)
O4—H4O	0.8401	C33—H33	0.9500
C2—C3	1.5275 (19)	C34—C35	1.379 (2)
C3—C31	1.5243 (18)	C34—H34	0.9500
C3—C4	1.5486 (19)	C35—C36	1.396 (2)
C4—C5	1.515 (2)	C35—H35	0.9500
C4—H4	1.0000	C36—H36	0.9500
C5—H5A	0.9900
C2—O1—C5	109.94 (11)	O1—C5—H5B	110.8
C3—O3—H3O	107.8	C4—C5—H5B	110.8
C4—O4—H4O	106.6	H5A—C5—H5B	108.8
O2—C2—O1	122.75 (13)	C36—C31—C32	119.22 (13)
O2—C2—C3	126.94 (14)	C36—C31—C3	122.46 (12)
O1—C2—C3	110.28 (12)	C32—C31—C3	118.24 (12)
O3—C3—C31	109.28 (10)	C33—C32—C31	120.24 (14)
O3—C3—C2	111.18 (11)	C33—C32—H32	119.9
C31—C3—C2	111.60 (10)	C31—C32—H32	119.9
O3—C3—C4	113.78 (11)	C34—C33—C32	120.46 (14)
C31—C3—C4	110.68 (10)	C34—C33—H33	119.8
C2—C3—C4	100.11 (11)	C32—C33—H33	119.8
O4—C4—C5	107.35 (11)	C35—C34—C33	119.55 (13)
O4—C4—C3	110.92 (11)	C35—C34—H34	120.2
C5—C4—C3	100.87 (11)	C33—C34—H34	120.2
O4—C4—H4	112.3	C34—C35—C36	120.39 (14)
C5—C4—H4	112.3	C34—C35—H35	119.8
C3—C4—H4	112.3	C36—C35—H35	119.8
O1—C5—C4	104.89 (11)	C31—C36—C35	120.14 (14)
O1—C5—H5A	110.8	C31—C36—H36	119.9
C4—C5—H5A	110.8	C35—C36—H36	119.9
C5—O1—C2—O2	172.88 (12)	C3—C4—C5—O1	33.83 (13)
C5—O1—C2—C3	−5.30 (14)	O3—C3—C31—C36	139.75 (13)
O2—C2—C3—O3	−31.23 (18)	C2—C3—C31—C36	16.37 (18)
O1—C2—C3—O3	146.85 (11)	C4—C3—C31—C36	−94.19 (15)
O2—C2—C3—C31	91.06 (16)	O3—C3—C31—C32	−43.46 (16)
O1—C2—C3—C31	−90.86 (13)	C2—C3—C31—C32	−166.83 (12)
O2—C2—C3—C4	−151.79 (13)	C4—C3—C31—C32	82.61 (15)
O1—C2—C3—C4	26.29 (13)	C36—C31—C32—C33	−0.3 (2)
O3—C3—C4—O4	−40.31 (15)	C3—C31—C32—C33	−177.20 (13)
C31—C3—C4—O4	−163.81 (11)	C31—C32—C33—C34	1.2 (2)
C2—C3—C4—O4	78.35 (12)	C32—C33—C34—C35	−0.9 (2)
O3—C3—C4—C5	−153.79 (11)	C33—C34—C35—C36	−0.4 (2)
C31—C3—C4—C5	82.71 (13)	C32—C31—C36—C35	−1.0 (2)
C2—C3—C4—C5	−35.13 (12)	C3—C31—C36—C35	175.79 (12)
C2—O1—C5—C4	−18.85 (14)	C34—C35—C36—C31	1.3 (2)
O4—C4—C5—O1	−82.33 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···O2i	0.84	1.95	2.7717 (19)	167
O4—H4o···O3ii	0.84	1.99	2.8188 (19)	168
C34—H34···O4iii	0.95	2.46	3.379 (2)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3o⋯O2i	0.84	1.95	2.7717 (19)	167
O4—H4o⋯O3ii	0.84	1.99	2.8188 (19)	168
C34—H34⋯O4iii	0.95	2.46	3.379 (2)	164

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