2-C-Phenyl­erythrono-1,4-lactone

Robinson, T.V.; Taylor, D.K.; Tiekink, E.R.T.

doi:10.1107/S1600536809048478

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3130

doi:10.1107/S1600536809048478

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2-C-Phenylerythrono-1,4-lactone

Tony V. Robinson,^a Dennis K. Taylor ^b ‡ and Edward R. T. Tiekink ^c ^*

^aDiscipline of Chemistry, University of Adelaide, 5005 South Australia, Australia, ^bDiscipline of Wine and Horticulture, University of Adelaide, Waite Campus, Glen, Osmond 5064, South Australia, Australia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 13 November 2009; accepted 15 November 2009; online 21 November 2009)

The title compound (systematic name: 3,4-dihydroxy-3-phenylfuran-2-one), C₁₀H₁₀O₄, features a five-membered γ-lactone ring with an envelope conformation at the C atom carrying the hydroxy group without the phenyl substituent. In the crystal, supramolecular 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_r = 194.18
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.128
S = 1.21
1834 reflections
133 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.27 e Å⁻³

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

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 ).

Supporting information

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

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

checkCIF report

Comment top

Our recent investigations into the dihydroxyation of the alkene component of 1,2-dioxines has allowed access to a diverse range of polyhydroxyated compounds (Robinson et al., 2006, 2009; Valente et al., 2009). Application of this methodology to the synthesis of erythrono-γ-lactones, such as the title compound, (I), provided a concise route to potassium (2R,3R)-2,3,4-trihydroxy-2-methylbutanoate (Pedersen et al., 2009), recently identified as a leaf-closing substance of the tropical legume Leucaena leucocephalam (Ueda et al., 2001; Gogoi & Argade, 2004; Koumbis et al., 2006).

The molecular structure of (I), Fig. 1, shows the five-membered γ-lactone ring to adopt an envelope conformation on the C4 atom, with this atom being orientated in the opposite direction to the phenyl ring. Both hydroxy substituents are orientated to the same side of the γ-lactone ring but the hydroxy-H atoms face opposite directions. This arrangement allows each molecule to bridge two neighbouring molecules via O—H_hydroxy···O_hydroxy hydrogen bonds resulting in the formation of ten-membered {···HOC₂O}₂ synthons and the construction of supramolecular chains aligned along the a direction, Fig. 2 and Table 1. The chains are consolidated in the 3-D crystal structure via C—H···O contacts, Fig. 3 and Table 1.

Related literature top

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 top

For full synthetic procedures and characterization data see Pedersen et al. (2009). To a solution of 2,3-O-isopropylidene-2-C-phenyl-erythrono-1,4-lactone (159 mg, 0.68 mmol) in MeOH (10 ml) was added activated 50 W Dowex X8 resin (~ 1 g), and the mixture was stirred at 343 K until complete by TLC (~2–3 days). The reaction was allowed to cool and then filtered to remove the Dowex. The methanol was removed under reduced pressure and the residue was purified by flash chromatography to furnish (I) (115 mg, 87%) as a colourless solid. The pure material was recrystallized from a small amount of dichloromethane which was allowed to slowly evaporate at ambient temperature producing colourless prisms, m.pt. 381–382 K

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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).

Figures top

	Fig. 1. Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 35% probability level.
	Fig. 2. Supramolecular chain formation along the a axis in (I) mediated by O—H···O hydrogen bonds (orange dashed lines).
	Fig. 3. View in projection along the a axis in (I) showing the C—H···O contacts (blue dashed lines) linking the supramolecular chains (aligned along a) stabilized by O—H···O hydrogen bonds (orange dashed lines).

3,4-dihydroxy-3-phenylfuran-2-one top

Crystal data top

C₁₀H₁₀O₄	F(000) = 408
M_r = 194.18	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0689P)² + 0.2568P] where P = (F_o² + 2F_c²)/3
1834 reflections	(Δ/σ)_max < 0.001
133 parameters	Δρ_max = 0.28 e Å⁻³
2 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₀H₁₀O₄	V = 888.6 (5) Å³
M_r = 194.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.485 (2) Å	µ = 0.11 mm⁻¹
b = 7.324 (3) Å	T = 173 K
c = 18.962 (7) Å	0.50 × 0.20 × 0.20 mm
β = 99.378 (7)°

Data collection top

Rigaku AFC12κ/SATURN724 diffractometer	1834 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1818 reflections with I > 2σ(I)
T_min = 0.778, T_max = 1.000	R_int = 0.028
21683 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	2 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.21	Δρ_max = 0.28 e Å⁻³
1834 reflections	Δρ_min = −0.27 e Å⁻³
133 parameters

Special details top

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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀O₄
M_r	194.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	6.485 (2), 7.324 (3), 18.962 (7)
β (°)	99.378 (7)
V (Å³)	888.6 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.50 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku AFC12κ/SATURN724 diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.778, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	21683, 1834, 1818
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.128, 1.21
No. of reflections	1834
No. of parameters	133
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.27

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

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

Footnotes

‡Additional correspondence author, e-mail: dennis.taylor@adelaide.edu.au.

Acknowledgements

We are grateful to the Australian Research Council for financial support. TVR thanks the Commonwealth Government of Australia for a postgraduate scholarship.

References

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