(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 3-carboxy­propanoate

Piotr Kuś; Marcin Rojkiewicz; Grzegorz Zięba; Monika Witoszek; Peter G Jones

doi:10.1107/S1600536809015190

. 2009 May 7;65(Pt 6):o1192. doi: 10.1107/S1600536809015190

(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 3-carboxypropanoate

Piotr Kuś ^a, Marcin Rojkiewicz ^a, Grzegorz Zięba ^a, Monika Witoszek ^a, Peter G Jones ^b,^*

PMCID: PMC2969742 PMID: 21583064

Abstract

In the title compound, C₁₀H₁₆O₆, the five-membered ring has an envelope conformation. The packing involves hydrogen-bonded carboxylic acid inversion dimers and three C—H⋯O interactions.

Related literature

For related literature, see: Osanai et al. (1997 ▶); Scriba (1993 ▶, 1995 ▶). The structure of a related derivative is reported in the preceeding paper, see: Kuś et al. (2009 ▶).

Experimental

Crystal data

C₁₀H₁₆O₆
M _r = 232.23
Monoclinic,
a = 20.7650 (12) Å
b = 5.7007 (3) Å
c = 9.6964 (7) Å
β = 98.658 (5)°
V = 1134.73 (12) Å³
Z = 4
Cu Kα radiation
μ = 0.96 mm⁻¹
T = 100 K
0.2 × 0.1 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with an Atlas (Nova) detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T _min = 0.880, T _max = 1.000 (expected range = 0.799–0.908)
10581 measured reflections
2304 independent reflections
2170 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.125
S = 1.14
2304 reflections
156 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1994 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015190/bt2936sup1.cif

e-65-o1192-sup1.cif^{(18.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015190/bt2936Isup2.hkl

e-65-o1192-Isup2.hkl^{(113.3KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H01⋯O2ⁱ	0.80 (3)	1.86 (3)	2.6582 (19)	175 (3)
C3—H3A⋯O3ⁱⁱ	0.99	2.36	3.211 (2)	144
C2—H2B⋯O4ⁱⁱⁱ	0.99	2.57	3.489 (2)	155
C7—H7B⋯O5^iv	0.99	2.60	3.506 (3)	152

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

Financial support by the Polish State Committee for Scientific Research (grant No. R0504303) is gratefully acknowledged.

supplementary crystallographic information

Comment

Isopropylidene groups are often used as protecting or activating units in polyhydroxyalkyl compounds used for synthesis of sugar-like derivatives; for a brief introduction and the structure of a related derivative, see the accompanying paper (Kuś et al., 2009).

Hemi-esters of succinic acid are often used for the synthesis of amphiphilic compounds with well organized structure (Osanai et al., 1997). Non-symmetrical esters of succinic acid have been used for the synthesis of prodrugs that release the corresponding drugs very slowly; e.g. steroid drugs (Scriba, 1995) or Phenytoin (Scriba, 1993). Solketal (D,L-isopropylideneglycerol, Aldrich) was used for the synthesis of compound 1.

The molecule of compound 1 is shown in Fig. 1. Bond lengths and angles may be regarded as normal. The chain C2 through to C7 has an approximately extended conformation (absolute torsion angles between 158 and 174°). The five-membered ring displays an envelope conformation, with local mirror symmetry about C8 and the midpoint of C6—C7.

The molecular packing (Fig. 2) is dominated by the formation of the well known carboxylic acid dimers via classical hydrogen bonding. Three further contacts, of the type C—H···O, link the molecules to a three-dimensional pattern.

Experimental

Compound 1 was obtained from solketal and succinic anhydride as described by Scriba (1993). Slow crystallization from petroleum ether gave crystals suitable for X-ray analysis. The analytical and spectroscopic data are consistent with the literature. M.p. 60° C. ¹H NMR (CDCl3, 400 MHz): δ 4.32 (q, 1H), 4.21–4.05 (m, 3H), 3.75–3.72 (dd, 1H), 2.67 (t, 4H), 1.43 (s, 3H), 1.36 (s, 3H). ¹³C NMR (100 MHz): δ 207.34, 172.10, 110.03, 73.62, 66.39, 65.13, 31.03, 28.97, 26.78, 25.46. MS (ESI): m/z (%) = 231 (100) [M—H]^-. IR: C═O at 1724, 1711 and 1694 cm^-1 (s), C—O at 1234 cm^-1 (m), 1,3-dioxalone at 975 cm^-1 (s).