Crystal structure of (5R)-5-[(1S)-1,2-di­hydroxy­eth­yl]-4-meth­oxy-3-phenyl-2,5-di­hydro­furan-2-one

Kote, S.R.; Thopate, S.R.; Gupta, S.K.; Butcher, R.J.

doi:10.1107/S1600536814021370

organic compounds

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ISSN: 2056-9890

Volume 70| Part 10| October 2014| Pages o1141-o1142

doi:10.1107/S1600536814021370

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Crystal structure of (5R)-5-[(1S)-1,2-dihydroxyethyl]-4-methoxy-3-phenyl-2,5-dihydrofuran-2-one

Santosh R. Kote,^a Shankar R. Thopate,^a ^* Sushil K. Gupta ^b and Ray J. Butcher ^c

^aDepartment of Chemistry, Post Graduate School for Biological Studies, Ahmednagar College, Ahmednagar 414 001, India, ^bSchool of Studies in Chemistry, Jiwaji University, Gwalior 474 011, India, and ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: srthopate@gmail.com

Edited by A. J. Lough, University of Toronto, Canada (Received 15 September 2014; accepted 26 September 2014; online 30 September 2014)

In the title compound, C₁₃H₁₄O₅, the furan ring is essentially planar [maximum deviation = 0.031 (3) Å] with a stereogenic center (R) at the sp³ hybridized C atom. The C atom bearing the dihydroxy 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 furanone group is twisted by 8.2 (4)° from that of the phenyl ring. In the crystal, molecules are linked by O—H⋯O hydrogen bonds involving furanone C=O groups and symmetry-related hydroxy groups, forming a two-dimensional network parallel to (001). Weak C—H⋯O hydrogen bonds are observed within the two-dimensional network.

Keywords: Crystal structure; L-ascorbic acid derivative; hydrogen bonding.; crystal structure.

CCDC references: 998610; 1026319

1. Related literature

For the biological activity of 5,6-O-modified and 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 ).

2. Experimental

2.1. Crystal data

C₁₃H₁₄O₅
M_r = 250.24
Monoclinic, P 2₁
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.126
S = 1.05
1243 reflections
166 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.15 e Å⁻³

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

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).

Supporting information

CCDC references: 998610; 1026319

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814021370/lh5729sup1.cif

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

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

checkCIF report

Comment top

5,6-O-modified L-ascorbic acid derivatives have been found to be effective anti-tumor agents for various human cancers, and induce apoptosis in tumor cells (Tanuma et al., 1993; Gazivoda et al., 2007; Wittine et al., 2012). We have recently reported that 2,3-di-O-alkyl derivatives of 5,6-O-isopropylidene-L-ascorbic acid exhibit anticancer activity against human breast cancer cell line (MCF-7), leukemic cell line (HL-60) and cervical cell line (HeLa) (Kote et al., 2014). A search of the Cambridge Structural Database (Version 5.35, updates to November 2013, Allen, 2002) revealed the crystal structures of four related compounds, viz. dimethyl-2',3,3', 3a',4,4a,5',6',6a',9a-decahydro-6'-hydroxy-1,3a',7,8,9a-pentamethoxy-2',10- dioxo-1,4-ethano-1H-pyrano(3,4-b)benzofuran-3-spiro-3'-furo(3,2-b)furan-4,5- dicarboxylate (Tanaka et al., 1986); 2,2-dimethyl-7-methoxy-1,3,6- trioxa-8-phenyl-4-(2,2-dimethyl-1,3-dioxacyclopropan-4-yl)bicyclo(4.3.0)nonane (Sugimura, 1990); 3,6-dihydroxy-7-methoxy-5-methyl-3-phenylhexahydro-2H-furo (3,2-b)pyran-2-one methanol solvate and 3,6,7-trihydroxy-5-methyl-3-phenyl- hexahydro-2H-furo(3,2-b)pyran-2-one (Koo & McDonald, 2005). In view of the importance of the title compound, (I), herein we report its synthesis and crystal structure.

In the title compound (Fig. 2) the furanone ring is essentially planar [maximum atomic deviation = 0.031 (3) Å] with a stereogenic center (R) at atom C9 and (S) at atom C11, which bears the dihydroxy ethyl group. The two O—H groups are in an anti conformation with respect to each other, as reflected by torsion angles O5—C12—C11—C9 of 170.5 (6)° and O4—C11—C12—O5 of -69.4 (6)°. The C—C, C_aromatic—C_aromatic, C—O and C═O bond lengths in (I) are within their normal ranges. The mean plane of the furan ring (C7/C8/O2/C9/C10) is twisted by 8.2 (4)° from that of the phenyl ring (C1–C6). In the crystal, molecules are linked by intermolecular O—H···O hydrogen bonds involving furanone C═O groups and symmetry-related hydroxy groups (Fig. 3, Table 1) to form a two-dimensional network paralllel to (001). Weak C—H···O hydrogen bonds are observed within the two-dimensional network.

Experimental top

Referring to Fig. 1, to a solution of (R)-5-((S)-2,2-dimethyl-1,3-dioxolan- 4-yl)-4-methoxy-3-phenylfuran-2-(5H)-one (0.570 g) in 5.0 mL THF was added 2.00 mL of 20% H₂SO₄ at room temperature. The reaction mixture was stirred for 6 h at room temperature before it was quenched with NaHCO₃ solution. The organic layer was extracted with ethyl acetate (3 × 10 mL), combined organic layer was dried over anhydrous Na₂SO₄, concentrated under vacuum and eluted through a silica column using a mixture of hexane and ethyl acetate (2:3) as an eluent to afford a white solid. Yield: 0.447 g (91%); HRMS: m/z = 251.0919 (calculated), m/z = 251.0927 [MH⁺] (found). ¹H NMR (DMSO-d₆ + CDCl₃): δ [ppm] = 6.90 (d, J = 7.2 Hz, 2H, Ar—H), 6.71 (m, 3H, Ar—H), 4.44 (s, 1H, C4—H), 4.14 (d, J = 6.0 Hz, 1H, C6—H), 3.95 (t, J = 6 Hz, 1H, C6—H), 3.43 (m, 1H, C5—H), 3.21 (s, 3H, -OCH3). ¹³C NMR (DMSO-d₆ + CDCl₃): δ [ppm] = 168.5, 168.4, 125.4, 125.0, 123.3, 123.0, 100.1, 72.4, 65.2, 58.2, 55.4. IR (KBr): 3349, 3268, 2958, 2920, 1713, 1628, 1465, 1312, 980, 781 cm^-1. [α]_D²⁵ +2.43° (c 0.28, MeOH). X-ray quality crystals were grown by slow evaporation of a solution of the title compound in a mixture of ethyl acetate and hexane.

Refinement top

H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H distances of 0.93–0.98 Å, O—H = 0.82Å and with U_iso(H) = 1.2–1.5 U_eq(C). In the absence of anomalous dispersion effects the Friedel pairs were merged before refinement. The absolute configuration is based on the precursor in the synthesis.

Related literature top

For the biological activity of 5,6-O-modified and 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).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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).

Figures top

	Fig. 1. Scheme showing the synthesis of the title compound.
	Fig. 2. The molecular structure of (I) showing 50% probability displacement ellipsoids.
	Fig. 3. The molecular packing of the title compound, viewed along the b-axis, showing two-dimensional network parallel to (001). Dashed lines indicate hydrogen bonds.

(5R)-5-[(1S)-1,2-dihydroxyethyl]-4-methoxy-3-phenyl-2,5-dihydrofuran-2-one top

Crystal data top

C₁₃H₁₄O₅	F(000) = 264
M_r = 250.24	D_x = 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

Data collection top

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

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.039P)²] where P = (F_o² + 2F_c²)/3
1243 reflections	(Δ/σ)_max < 0.001
166 parameters	Δρ_max = 0.13 e Å⁻³
1 restraint	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₃H₁₄O₅	V = 615.97 (8) Å³
M_r = 250.24	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.5110 (5) Å	µ = 0.10 mm⁻¹
b = 4.9298 (3) Å	T = 293 K
c = 16.6625 (16) Å	0.4 × 0.3 × 0.08 mm
β = 93.268 (6)°

Data collection top

Agilent Xcalibur, Ruby, Gemini diffractometer	1243 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	655 reflections with I > 2σ(I)
T_min = 0.714, T_max = 1.000	R_int = 0.034
8346 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	1 restraint
wR(F²) = 0.126	H-atom parameters constrained
S = 1.05	Δρ_max = 0.13 e Å⁻³
1243 reflections	Δρ_min = −0.15 e Å⁻³
166 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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O5ⁱ	0.82	1.89	2.707 (5)	177.9
O5—H5···O1ⁱⁱ	0.82	1.94	2.741 (6)	165.4
C12—H12B···O4ⁱⁱⁱ	0.97	2.58	3.365 (8)	138.5

Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) −x+2, y+1/2, −z+1; (iii) x, y+1, z.

Acknowledgements

This work was supported by the Department of Science and Technology (DST), New Delhi, India (No. SR/S1/OC-19/2007). SRK thanks the DST for the award of a JRF. RJB acknowledges the NSF–MRI program (grant No. CHE0619278) for funds to purchase the X-ray diffractometer. SKG wishes to thank the USIEF for the award of a Fulbright–Nehru Senior Research Fellowship.

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Volume 70| Part 10| October 2014| Pages o1141-o1142

doi:10.1107/S1600536814021370

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

Crystal structure of (5R)-5-[(1S)-1,2-di­hy­droxy­eth­yl]-4-meth­­oxy-3-phenyl-2,5-di­hydro­furan-2-one

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of (5R)-5-[(1S)-1,2-dihydroxyethyl]-4-methoxy-3-phenyl-2,5-dihydrofuran-2-one