1-(2-Hy­droxy­eth­yl)pyrrole-2,5-dione

Xue-Jie Tan; Ting-Wen Du; Dian-Xiang Xing; Yun Liu

doi:10.1107/S1600536812008938

. 2012 Mar 7;68(Pt 4):o970. doi: 10.1107/S1600536812008938

1-(2-Hydroxyethyl)pyrrole-2,5-dione

Xue-Jie Tan ^a,^*, Ting-Wen Du ^a, Dian-Xiang Xing ^a, Yun Liu ^a

PMCID: PMC3343945 PMID: 22590026

Abstract

The asymmetric unit of the title compound, C₆H₇NO₃, contains two molecules (A and B) related by a non-crystallographic twofold pseudo-axis. The molecules are joined in the (AABB)_n manner by O—H⋯O hydrogen bonds between their hydroxy groups, thus forming C(2) chains along the a-axis direction. Neighboring molecules of the same kind (A and A, or B and B) are related by inversion centers, so that all hydroxy H atoms are disordered other two sets of sites with half occupancies (superimposed O—H⋯O and O⋯H—O fragments). The molecules are further linked by C—H⋯O interactions, which can be considered to be weak hydrogen bonds.

Related literature

For self-initiated photopolymerization, see: Cheng et al. (2006 ▶); Ericsson (2001 ▶). For photopolymerization of N-substituted maleimides, see: Yamada et al. (1968 ▶). For applications of similar compounds, see: Stang & White (2011 ▶); Sanchez et al. (2011 ▶); Keller et al. (2005 ▶). For the synthesis of the title compound, see: Yamada et al. (1961 ▶); Gramlich et al. (2010 ▶); Heath et al. (2008 ▶).

Experimental

Crystal data

C₆H₇NO₃
M _r = 141.13
Monoclinic,
a = 7.734 (4) Å
b = 9.701 (5) Å
c = 17.673 (8) Å
β = 96.660 (7)°
V = 1317.0 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 K
0.45 × 0.29 × 0.26 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.962, T _max = 0.976
7522 measured reflections
3003 independent reflections
1972 reflections with I > 2σ(I)
R _int = 0.060

Refinement

R[F ² > 2σ(F ²)] = 0.081
wR(F ²) = 0.217
S = 1.10
3003 reflections
201 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812008938/yk2042sup1.cif

e-68-0o970-sup1.cif^{(21.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008938/yk2042Isup2.hkl

e-68-0o970-Isup2.hkl^{(147.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812008938/yk2042Isup3.cml

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
C3A—H3A⋯O2Bⁱⁱⁱ	0.93	2.38	3.188 (4)	146
C4B—H4B⋯O5Aⁱ	0.93	2.49	3.114 (4)	125
O12A—H12A⋯O12B	0.82 (1)	1.91 (1)	2.688 (3)	158 (3)
O12A—H12C⋯O12Aⁱ	0.82 (1)	2.01 (4)	2.702 (5)	142 (7)
O12B—H12B⋯O12A	0.82 (1)	1.88 (2)	2.688 (3)	168 (8)
O12B—H12D⋯O12Bⁱⁱ	0.82 (1)	1.98 (2)	2.773 (4)	163 (5)

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

Acknowledgments

This work was supported by the Science & Technology Development Project of Shandong Province in China (No. 2011GGB01164), the National Natural Science Foundation of China (NSFC, No. 21103100) and the Natural Science Foundation of Shandong Province in China (No. ZR2009BM040).

supplementary crystallographic information

Comment

Maleimides are a class of reactive "synthons" having a polymerizable double bond. They are particularly useful in manufacturing oligomers capable of self-initiated photopolymerization (Cheng et al., 2006; Ericsson, 2001). The title compound, N-2-hydroxyethylmaleimide, first prepared in 1961 (Yamada et al., 1961), is a well-known maleimide that has been intensively studied during last years (Stang & White, 2011; Sanchez et al., 2011; Keller et al., 2005). However its crystal structure has not been determined. In this work, the crystal structure of the title compound is reported, and its molecular packing mode is discussed.

As shown in Fig. 1, the asymmetric unit of the title compound contains two molecules (A and B) related by the non-crystallographic two-fold pseudo-axis. The molecules are joined in the (AABB)_n manner by O—H···O hydrogen bonds between their hydroxy groups, thus forming the C(2) chains stretched along the a-axis direction. The neighboring molecules of the same kind (A and A, or B and B) are related by inversion centers, so that all hydroxy hydrogen atoms are disordered other two sets of sites with half occupancies, thus the fragments O—H···O and O···H—O are superimposed. The molecules are further linked by intermolecular C—H···O interactions, which can be considered as weak hydrogen bonds.

Instead of helices, hydrogen bonds make (I) pack into zigzag-type pleated sheets stretched along (0 0 1) planes (Fig. 2). Adjacent sheets are arranged in an antiparallel manner, yielding an ABAB layer sequence. Either O—H···O and C—H···O interactions or no such interactions occur between adjacent sheets. As can be seen, the hydrogen-bonded sheets are rather closely spaced in the lattice (3.9103 (9) Å) than no-hydrogen-bonded sheets (4.9262 (8) Å).

Experimental

The title compound was synthesized using established method (Gramlich et al., 2010; Heath et al., 2008). Elemental analysis: Calcd: C 51.06; H 5.00; N 9.93%. Found: C 51.11; H 4.92; N 10.02%.