Crystal structure of (5R)-5-[(1S)-1,2-di-hydroxy-eth-yl]-4-meth-oxy-3-phenyl-2,5-di-hydro-furan-2-one.

In the title compound, C13H14O5, the furan ring is essentially planar [maximum deviation = 0.031 (3) Å] with a stereogenic center (R) at the sp (3) hybridized C atom. The C atom bearing the dihy-droxy ethyl group is S. The absolute configuration is based on the precursor in the synthesis. The two O-H groups are in an anti conformation with respect to each other. The mean plane of the furan-one group is twisted by 8.2 (4)° from that of the phenyl ring. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds involving furan-one C=O groups and symmetry-related hy-droxy groups, forming a two-dimensional network parallel to (001). Weak C-H⋯O hydrogen bonds are observed within the two-dimensional network.

Related literature

For the biological activity of 5,6-O-modified and <span class="Chemical">2,3-di-O-alkyl derivatives of l-ascorbic acid, see: Tanuma et al. (1993 ▶); Gazivoda et al. (2007 ▶); Wittine et al. (2012 ▶); Kote et al. (2014 ▶). For related structures, see: Koo & McDonald (2005 ▶); Tanaka et al. (1986 ▶); Sugimura (1990 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C13H14O5

M = 250.24

Monoclinic,

a = 7.5110 (5) Å

b = 4.9298 (3) Å

c = 16.6625 (16) Å

β = 93.268 (6)°

V = 615.97 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.4 × 0.3 × 0.08 mm

Data collection

Agilent Xcalibur, Ruby, Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.714, T max = 1.000

8346 measured reflections

1243 independent reflections

655 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.126

S = 1.05

1243 reflections

166 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2014/6 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814021370/lh5729sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814021370/lh5729Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814021370/lh5729Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814021370/lh5729fig1.tif

Scheme showing the synthesis of the title compound.

Click here for additional data file.

. DOI: 10.1107/S1600536814021370/lh5729fig2.tif

The mol­ecular structure of (I) showing 50% probability displacement ellipsoids.

Click here for additional data file.

b . DOI: 10.1107/S1600536814021370/lh5729fig3.tif

The mol­ecular packing of the title compound, viewed along the b-axis, showing two-dimensional network parallel to (001). Dashed lines indicate hydrogen bonds.

CCDC references: 998610, 1026319

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H14O5	F(000) = 264
Mr = 250.24	Dx = 1.349 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 7.5110 (5) Å	Cell parameters from 613 reflections
b = 4.9298 (3) Å	θ = 3.6–28.4°
c = 16.6625 (16) Å	µ = 0.10 mm−1
β = 93.268 (6)°	T = 293 K
V = 615.97 (8) Å3	Plate, colorless
Z = 2	0.4 × 0.3 × 0.08 mm

Agilent Xcalibur, Ruby, Gemini diffractometer	1243 independent reflections
Radiation source: Enhance (Mo) X-ray Source	655 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 10.5081 pixels mm-1	θmax = 25.3°, θmin = 3.6°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = 0→5
Tmin = 0.714, Tmax = 1.000	l = 0→19
8346 measured reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.039P)2] where P = (Fo2 + 2Fc2)/3
1243 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.13 e Å−3
1 restraint	Δρmin = −0.15 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.

	x	y	z	Uiso*/Ueq
O1	1.1330 (5)	0.1548 (13)	0.2979 (3)	0.0999 (17)
O2	0.9642 (4)	0.4569 (9)	0.3574 (3)	0.0705 (13)
O3	0.5525 (5)	0.4727 (10)	0.2375 (3)	0.0830 (14)
O4	0.6722 (4)	0.1838 (8)	0.4222 (3)	0.0727 (13)
H4	0.5683	0.1386	0.4272	0.109*
O5	0.6695 (4)	0.5242 (11)	0.5641 (2)	0.0776 (14)
H5	0.7173	0.5875	0.6054	0.116*
C1	0.8238 (8)	0.0846 (12)	0.1705 (4)	0.0609 (16)
C2	0.6797 (10)	0.0982 (15)	0.1143 (5)	0.090 (2)
H2A	0.5888	0.2215	0.1225	0.108*
C3	0.6670 (12)	−0.0633 (19)	0.0476 (5)	0.107 (3)
H3A	0.5686	−0.0482	0.0114	0.128*
C4	0.7970 (13)	−0.2454 (16)	0.0338 (5)	0.098 (3)
H4A	0.7883	−0.3561	−0.0114	0.117*
C5	0.9404 (11)	−0.2637 (16)	0.0873 (6)	0.100 (3)
H5A	1.0301	−0.3882	0.0783	0.120*
C6	0.9552 (9)	−0.1003 (15)	0.1549 (5)	0.085 (2)
H6A	1.0551	−0.1154	0.1903	0.102*
C7	0.8339 (7)	0.2571 (12)	0.2420 (4)	0.0565 (17)
C8	0.9895 (8)	0.2716 (15)	0.2967 (4)	0.071 (2)
C9	0.7819 (6)	0.5560 (13)	0.3479 (4)	0.0609 (16)
H9	0.7814	0.7541	0.3428	0.073*
C10	0.7144 (7)	0.4319 (12)	0.2723 (4)	0.0602 (17)
C11	0.6847 (7)	0.4704 (14)	0.4227 (4)	0.0584 (16)
H11A	0.5640	0.5469	0.4189	0.070*
C12	0.7805 (7)	0.5703 (14)	0.4989 (4)	0.0681 (18)
H12A	0.8925	0.4742	0.5081	0.082*
H12B	0.8061	0.7624	0.4944	0.082*
C13	0.4443 (8)	0.6955 (16)	0.2630 (4)	0.094 (2)
H13A	0.3670	0.7554	0.2186	0.142*
H13B	0.5201	0.8424	0.2812	0.142*
H13C	0.3739	0.6366	0.3060	0.142*

	U11	U22	U33	U12	U13	U23
O1	0.061 (2)	0.158 (5)	0.081 (4)	0.027 (3)	0.005 (2)	0.004 (3)
O2	0.054 (2)	0.090 (3)	0.068 (3)	−0.011 (2)	0.003 (2)	0.000 (3)
O3	0.071 (2)	0.092 (3)	0.083 (4)	0.024 (3)	−0.018 (2)	−0.017 (3)
O4	0.066 (2)	0.060 (3)	0.094 (4)	−0.006 (2)	0.016 (2)	0.002 (2)
O5	0.060 (2)	0.113 (4)	0.061 (3)	0.005 (2)	0.011 (2)	0.006 (3)
C1	0.069 (4)	0.056 (4)	0.058 (5)	0.000 (3)	0.007 (4)	0.001 (4)
C2	0.109 (5)	0.084 (6)	0.077 (6)	0.017 (5)	0.000 (5)	−0.015 (5)
C3	0.125 (6)	0.104 (7)	0.090 (7)	0.010 (6)	−0.008 (5)	−0.019 (6)
C4	0.148 (7)	0.077 (6)	0.070 (7)	−0.009 (6)	0.025 (6)	−0.011 (5)
C5	0.110 (6)	0.086 (6)	0.107 (8)	0.013 (5)	0.039 (6)	−0.014 (6)
C6	0.079 (4)	0.087 (6)	0.091 (6)	0.014 (4)	0.015 (4)	−0.005 (5)
C7	0.053 (3)	0.056 (4)	0.061 (5)	0.001 (3)	0.007 (3)	0.007 (4)
C8	0.063 (4)	0.087 (6)	0.064 (5)	−0.003 (4)	0.012 (4)	0.004 (4)
C9	0.056 (3)	0.058 (4)	0.068 (5)	−0.002 (3)	−0.001 (3)	0.006 (4)
C10	0.054 (3)	0.062 (4)	0.063 (5)	−0.004 (4)	−0.002 (3)	0.006 (4)
C11	0.051 (3)	0.056 (4)	0.068 (5)	−0.005 (3)	0.007 (3)	0.002 (4)
C12	0.061 (3)	0.077 (4)	0.066 (5)	−0.009 (3)	0.007 (3)	−0.002 (4)
C13	0.077 (4)	0.097 (6)	0.109 (7)	0.025 (5)	0.001 (4)	−0.004 (5)

O1—C8	1.221 (7)	C4—H4A	0.9300
O2—C8	1.384 (8)	C5—C6	1.384 (10)
O2—C9	1.454 (6)	C5—H5A	0.9300
O3—C10	1.332 (6)	C6—H6A	0.9300
O3—C13	1.445 (7)	C7—C10	1.362 (7)
O4—C11	1.416 (7)	C7—C8	1.442 (8)
O4—H4	0.8200	C9—C10	1.464 (8)
O5—C12	1.424 (6)	C9—C11	1.539 (7)
O5—H5	0.8200	C9—H9	0.9800
C1—C6	1.379 (8)	C11—C12	1.507 (8)
C1—C2	1.392 (8)	C11—H11A	0.9800
C1—C7	1.462 (8)	C12—H12A	0.9700
C2—C3	1.367 (10)	C12—H12B	0.9700
C2—H2A	0.9300	C13—H13A	0.9600
C3—C4	1.355 (10)	C13—H13B	0.9600
C3—H3A	0.9300	C13—H13C	0.9600
C4—C5	1.362 (9)
C8—O2—C9	108.0 (5)	O2—C9—C10	103.4 (5)
C10—O3—C13	120.1 (5)	O2—C9—C11	107.8 (5)
C11—O4—H4	109.5	C10—C9—C11	115.1 (5)
C12—O5—H5	109.5	O2—C9—H9	110.1
C6—C1—C2	116.3 (6)	C10—C9—H9	110.1
C6—C1—C7	122.3 (6)	C11—C9—H9	110.1
C2—C1—C7	121.5 (6)	O3—C10—C7	122.6 (6)
C3—C2—C1	122.3 (7)	O3—C10—C9	125.1 (5)
C3—C2—H2A	118.8	C7—C10—C9	112.3 (5)
C1—C2—H2A	118.8	O4—C11—C12	111.0 (5)
C4—C3—C2	120.4 (8)	O4—C11—C9	107.7 (5)
C4—C3—H3A	119.8	C12—C11—C9	111.5 (5)
C2—C3—H3A	119.8	O4—C11—H11A	108.8
C3—C4—C5	118.9 (8)	C12—C11—H11A	108.8
C3—C4—H4A	120.5	C9—C11—H11A	108.8
C5—C4—H4A	120.5	O5—C12—C11	108.6 (4)
C4—C5—C6	121.2 (7)	O5—C12—H12A	110.0
C4—C5—H5A	119.4	C11—C12—H12A	110.0
C6—C5—H5A	119.4	O5—C12—H12B	110.0
C1—C6—C5	120.8 (7)	C11—C12—H12B	110.0
C1—C6—H6A	119.6	H12A—C12—H12B	108.4
C5—C6—H6A	119.6	O3—C13—H13A	109.5
C10—C7—C8	105.2 (6)	O3—C13—H13B	109.5
C10—C7—C1	131.7 (6)	H13A—C13—H13B	109.5
C8—C7—C1	123.1 (6)	O3—C13—H13C	109.5
O1—C8—O2	117.1 (6)	H13A—C13—H13C	109.5
O1—C8—C7	132.0 (7)	H13B—C13—H13C	109.5
O2—C8—C7	110.8 (5)
C6—C1—C2—C3	0.5 (10)	C8—O2—C9—C10	−5.6 (6)
C7—C1—C2—C3	−179.3 (6)	C8—O2—C9—C11	116.8 (5)
C1—C2—C3—C4	0.1 (12)	C13—O3—C10—C7	−168.3 (5)
C2—C3—C4—C5	−0.3 (12)	C13—O3—C10—C9	14.6 (8)
C3—C4—C5—C6	0.0 (12)	C8—C7—C10—O3	−179.8 (5)
C2—C1—C6—C5	−0.8 (9)	C1—C7—C10—O3	0.7 (9)
C7—C1—C6—C5	179.0 (6)	C8—C7—C10—C9	−2.4 (6)
C4—C5—C6—C1	0.6 (11)	C1—C7—C10—C9	178.2 (5)
C6—C1—C7—C10	−173.2 (6)	O2—C9—C10—O3	−177.6 (5)
C2—C1—C7—C10	6.6 (9)	C11—C9—C10—O3	65.0 (8)
C6—C1—C7—C8	7.5 (8)	O2—C9—C10—C7	5.0 (6)
C2—C1—C7—C8	−172.7 (6)	C11—C9—C10—C7	−112.4 (6)
C9—O2—C8—O1	−175.9 (5)	O2—C9—C11—O4	−66.2 (6)
C9—O2—C8—C7	4.6 (6)	C10—C9—C11—O4	48.7 (6)
C10—C7—C8—O1	179.2 (7)	O2—C9—C11—C12	55.9 (7)
C1—C7—C8—O1	−1.4 (10)	C10—C9—C11—C12	170.7 (5)
C10—C7—C8—O2	−1.4 (6)	O4—C11—C12—O5	−69.4 (6)
C1—C7—C8—O2	178.1 (5)	C9—C11—C12—O5	170.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O5i	0.82	1.89	2.707 (5)	178
O5—H5···O1ii	0.82	1.94	2.741 (6)	165
C12—H12B···O4iii	0.97	2.58	3.365 (8)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O5i	0.82	1.89	2.707 (5)	178
O5—H5⋯O1ii	0.82	1.94	2.741 (6)	165
C12—H12B⋯O4iii	0.97	2.58	3.365 (8)	139

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