1-(2-Hy-droxy-eth-yl)pyrrole-2,5-dione.

The asymmetric unit of the title compound, C(6)H(7)NO(3), contains two mol-ecules (A and B) related by a non-crystallographic twofold pseudo-axis. The mol-ecules are joined in the (AABB)(n) manner by O-H⋯O hydrogen bonds between their hy-droxy groups, thus forming C(2) chains along the a-axis direction. Neighboring mol-ecules of the same kind (A and A, or B and B) are related by inversion centers, so that all hy-droxy H atoms are disordered other two sets of sites with half occupancies (superimposed O-H⋯O and O⋯H-O fragments). The mol-ecules are further linked by C-H⋯O inter-actions, 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 = 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

Δρmax = 0.38 e Å−3

Δρmin = −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.

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

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

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

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

C6H7NO3	F(000) = 592.0
Mr = 141.13	Dx = 1.424 Mg m−3
Monoclinic, P21/c	Melting point: 344 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.734 (4) Å	Cell parameters from 380 reflections
b = 9.701 (5) Å	θ = 2.5–28.3°
c = 17.673 (8) Å	µ = 0.12 mm−1
β = 96.660 (7)°	T = 293 K
V = 1317.0 (11) Å3	Block, colourless
Z = 8	0.45 × 0.29 × 0.26 mm

Bruker SMART CCD diffractometer	3003 independent reflections
Radiation source: fine-focus sealed tube	1972 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
φ and ω scans	θmax = 28.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→10
Tmin = 0.962, Tmax = 0.976	k = −11→12
7522 measured reflections	l = −23→23

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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.217	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.097P)2 + 0.420P] where P = (Fo2 + 2Fc2)/3
3003 reflections	(Δ/σ)max = 0.001
201 parameters	Δρmax = 0.38 e Å−3
8 restraints	Δρmin = −0.29 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O2A	0.2520 (4)	1.0076 (3)	0.5604 (2)	0.0911 (10)
O5A	0.2601 (3)	0.5693 (2)	0.64576 (16)	0.0653 (7)
O12A	0.4289 (3)	0.6222 (3)	0.47672 (15)	0.0617 (7)
H12A	0.3228 (14)	0.630 (4)	0.475 (5)	0.093*	0.50
H12B	0.1884 (13)	0.594 (5)	0.452 (5)	0.093*	0.50
O2B	0.2505 (3)	0.9305 (2)	0.33843 (17)	0.0709 (8)
O5B	0.2400 (3)	0.4751 (2)	0.28146 (15)	0.0622 (7)
O12B	0.0831 (3)	0.5827 (2)	0.45141 (14)	0.0529 (6)
H12C	0.450 (9)	0.561 (3)	0.508 (2)	0.079*	0.50
H12D	0.023 (5)	0.548 (6)	0.481 (4)	0.079*	0.50
N1A	0.3035 (3)	0.7840 (2)	0.59889 (14)	0.0440 (6)
N1B	0.1968 (3)	0.7013 (2)	0.31464 (13)	0.0369 (6)
C2A	0.2026 (5)	0.9003 (3)	0.5835 (2)	0.0544 (8)
C3A	0.0255 (5)	0.8636 (4)	0.6022 (2)	0.0607 (9)
H3A	−0.0708	0.9216	0.5973	0.073*
C4A	0.0275 (4)	0.7364 (4)	0.62661 (18)	0.0527 (8)
H4A	−0.0669	0.6888	0.6420	0.063*
C5A	0.2058 (4)	0.6808 (3)	0.62565 (17)	0.0435 (7)
C11A	0.4858 (4)	0.7719 (3)	0.5876 (2)	0.0510 (8)
H111	0.5380	0.6972	0.6189	0.061*
H112	0.5458	0.8564	0.6040	0.061*
C12A	0.5090 (4)	0.7447 (4)	0.5057 (2)	0.0583 (9)
H121	0.4612	0.8216	0.4751	0.070*
H122	0.6325	0.7398	0.5009	0.070*
C2B	0.2981 (4)	0.8183 (3)	0.32075 (18)	0.0436 (7)
C3B	0.4715 (4)	0.7761 (3)	0.30062 (19)	0.0483 (8)
H3B	0.5671	0.8340	0.2997	0.058*
C4B	0.4683 (4)	0.6462 (3)	0.28466 (18)	0.0468 (8)
H4B	0.5613	0.5957	0.2702	0.056*
C5B	0.2936 (4)	0.5904 (3)	0.29288 (17)	0.0412 (7)
C11B	0.0143 (4)	0.6925 (3)	0.32856 (17)	0.0432 (7)
H113	−0.0359	0.6087	0.3055	0.052*
H114	−0.0489	0.7700	0.3041	0.052*
C12B	−0.0084 (4)	0.6927 (3)	0.41195 (19)	0.0491 (8)
H123	0.0332	0.7795	0.4343	0.059*
H124	−0.1313	0.6850	0.4177	0.059*

	U11	U22	U33	U12	U13	U23
O2A	0.089 (2)	0.0435 (16)	0.144 (3)	0.0012 (14)	0.0289 (19)	0.0214 (17)
O5A	0.0582 (15)	0.0482 (14)	0.0865 (19)	−0.0029 (11)	−0.0048 (13)	0.0229 (13)
O12A	0.0487 (13)	0.0734 (17)	0.0628 (16)	0.0004 (12)	0.0055 (12)	−0.0066 (12)
O2B	0.0717 (17)	0.0406 (14)	0.105 (2)	0.0016 (11)	0.0321 (15)	−0.0125 (13)
O5B	0.0615 (15)	0.0379 (13)	0.0905 (19)	−0.0007 (10)	0.0232 (13)	−0.0092 (12)
O12B	0.0448 (12)	0.0588 (14)	0.0561 (14)	−0.0039 (11)	0.0105 (11)	0.0157 (11)
N1A	0.0459 (14)	0.0391 (14)	0.0468 (14)	−0.0010 (11)	0.0048 (11)	0.0041 (11)
N1B	0.0362 (12)	0.0353 (13)	0.0407 (13)	0.0040 (10)	0.0109 (10)	0.0037 (10)
C2A	0.066 (2)	0.0370 (18)	0.060 (2)	0.0050 (15)	0.0101 (17)	0.0021 (15)
C3A	0.060 (2)	0.053 (2)	0.072 (2)	0.0157 (16)	0.0204 (18)	−0.0029 (18)
C4A	0.0535 (19)	0.061 (2)	0.0456 (18)	−0.0009 (16)	0.0136 (15)	−0.0041 (15)
C5A	0.0464 (17)	0.0445 (17)	0.0388 (15)	−0.0010 (13)	0.0011 (12)	0.0060 (13)
C11A	0.0379 (16)	0.0485 (18)	0.065 (2)	−0.0061 (14)	0.0005 (14)	−0.0005 (16)
C12A	0.0439 (18)	0.062 (2)	0.071 (2)	−0.0044 (16)	0.0140 (16)	0.0094 (18)
C2B	0.0481 (17)	0.0371 (16)	0.0468 (17)	0.0009 (13)	0.0109 (13)	0.0052 (13)
C3B	0.0433 (17)	0.0446 (18)	0.0588 (19)	−0.0076 (13)	0.0133 (14)	0.0083 (15)
C4B	0.0428 (17)	0.0435 (17)	0.0567 (19)	0.0110 (13)	0.0170 (14)	0.0131 (14)
C5B	0.0479 (17)	0.0338 (16)	0.0427 (16)	0.0073 (12)	0.0089 (13)	0.0064 (12)
C11B	0.0368 (15)	0.0454 (17)	0.0484 (17)	0.0037 (12)	0.0092 (13)	0.0045 (13)
C12B	0.0490 (18)	0.0458 (18)	0.0565 (19)	0.0015 (14)	0.0227 (15)	0.0005 (15)

O2A—C2A	1.196 (4)	C3A—H3A	0.9300
O5A—C5A	1.199 (4)	C4A—C5A	1.483 (4)
O12A—C12A	1.409 (4)	C4A—H4A	0.9300
O12A—H12A	0.821 (10)	C11A—C12A	1.503 (5)
O12A—H12C	0.821 (10)	C11A—H111	0.9700
O2B—C2B	1.202 (4)	C11A—H112	0.9700
O5B—C5B	1.201 (4)	C12A—H121	0.9700
O12B—C12B	1.418 (4)	C12A—H122	0.9700
O12B—H12B	0.821 (10)	C2B—C3B	1.484 (4)
O12B—H12D	0.817 (10)	C3B—C4B	1.291 (4)
N1A—C5A	1.371 (4)	C3B—H3B	0.9300
N1A—C2A	1.381 (4)	C4B—C5B	1.478 (4)
N1A—C11A	1.452 (4)	C4B—H4B	0.9300
N1B—C2B	1.376 (4)	C11B—C12B	1.504 (4)
N1B—C5B	1.391 (4)	C11B—H113	0.9700
N1B—C11B	1.463 (4)	C11B—H114	0.9700
C2A—C3A	1.489 (5)	C12B—H123	0.9700
C3A—C4A	1.307 (5)	C12B—H124	0.9700
C12A—O12A—H12A	110 (2)	O12A—C12A—C11A	113.7 (3)
C12A—O12A—H12C	109 (2)	O12A—C12A—H121	108.8
H12A—O12A—H12C	102 (8)	C11A—C12A—H121	108.8
C12B—O12B—H12B	110 (2)	O12A—C12A—H122	108.8
C12B—O12B—H12D	110 (2)	C11A—C12A—H122	108.8
H12B—O12B—H12D	133 (6)	H121—C12A—H122	107.7
C5A—N1A—C2A	110.1 (3)	O2B—C2B—N1B	125.3 (3)
C5A—N1A—C11A	124.8 (3)	O2B—C2B—C3B	128.6 (3)
C2A—N1A—C11A	125.1 (3)	N1B—C2B—C3B	106.0 (2)
C2B—N1B—C5B	109.9 (2)	C4B—C3B—C2B	109.1 (3)
C2B—N1B—C11B	125.9 (2)	C4B—C3B—H3B	125.5
C5B—N1B—C11B	124.2 (2)	C2B—C3B—H3B	125.5
O2A—C2A—N1A	125.6 (3)	C3B—C4B—C5B	109.3 (3)
O2A—C2A—C3A	128.5 (3)	C3B—C4B—H4B	125.3
N1A—C2A—C3A	105.9 (3)	C5B—C4B—H4B	125.3
C4A—C3A—C2A	108.9 (3)	O5B—C5B—N1B	125.5 (3)
C4A—C3A—H3A	125.6	O5B—C5B—C4B	128.7 (3)
C2A—C3A—H3A	125.6	N1B—C5B—C4B	105.7 (2)
C3A—C4A—C5A	108.4 (3)	N1B—C11B—C12B	112.9 (3)
C3A—C4A—H4A	125.8	N1B—C11B—H113	109.0
C5A—C4A—H4A	125.8	C12B—C11B—H113	109.0
O5A—C5A—N1A	125.0 (3)	N1B—C11B—H114	109.0
O5A—C5A—C4A	128.2 (3)	C12B—C11B—H114	109.0
N1A—C5A—C4A	106.8 (3)	H113—C11B—H114	107.8
N1A—C11A—C12A	111.9 (3)	O12B—C12B—C11B	111.9 (2)
N1A—C11A—H111	109.2	O12B—C12B—H123	109.2
C12A—C11A—H111	109.2	C11B—C12B—H123	109.2
N1A—C11A—H112	109.2	O12B—C12B—H124	109.2
C12A—C11A—H112	109.2	C11B—C12B—H124	109.2
H111—C11A—H112	107.9	H123—C12B—H124	107.9

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

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)

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