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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 4| April 2012| Page o970
doi:10.1107/S1600536812008938

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

Xue-Jie Tan,a* Ting-Wen Du,a Dian-Xiang Xinga and Yun Liua

aSchool of Chemical and Pharmaceutical Engineering, Shandong Institute of Light Industry, Jinan 250353, People's Republic of China
*Correspondence e-mail: tanxuejie@163.com

(Received 28 January 2012; accepted 29 February 2012; online 7 March 2012)

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[Cheng, Ch. H., Sabahi, M., Sulzer, G. M. & Ramachandran, V. (2006). US Patent Appl. 2006035386.]); Ericsson (2001[Ericsson, J. (2001). Int. Patent Appl. 2001000510.]). For photopolymerization of N-substituted maleimides, see: Yamada et al. (1968[Yamada, M., Takase, I. & Koutou, N. (1968). J. Polym. Sci. B, 6, 883-888.]). For applications of similar compounds, see: Stang & White (2011[Stang, E. M. & White, M. C. (2011). J. Am. Chem. Soc. 133, 14892-14895.]); Sanchez et al. (2011[Sanchez, A., Pedroso, E. & Grandas, A. (2011). Org. Lett. 13, 4364-4367.]); Keller et al. (2005[Keller, K. A., Guo, J., Punna, S. & Finn, M. G. (2005). Tetrahedron Lett. 46, 1181-1184.]). For the synthesis of the title compound, see: Yamada et al. (1961[Yamada, M., Takase, I., Hayashi, K., Hashimoto, Y. & Komiya, Y. (1961). J. Soc. Org. Synth. Chem. (Jpn), 23, 166-170.]); Gramlich et al. (2010[Gramlich, W. M., Robertson, M. L. & Hillmyer, M. A. (2010). Macromolecules, 43, 2313-2321.]); Heath et al. (2008[Heath, W. H., Palmieri, F., Adams, J. R., Long, B. K., Chute, J., Holcombe, T. W., Zieren, S., Truitt, M. J., White, J. L. & Willson, C. G. (2008). Macromolecules, 41, 719-726.]).

[Scheme 1]

Experimental

Crystal data

  • C6H7NO3

  • Mr = 141.13

  • Monoclinic, P 21 /c

  • 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[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.962, Tmax = 0.976

  • 7522 measured reflections

  • 3003 independent reflections

  • 1972 reflections with I > 2σ(I)

  • Rint = 0.060
Refinement

  • R[F2 > 2σ(F2)] = 0.081

  • wR(F2) = 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

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

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812008938/yk2042sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812008938/yk2042Isup3.cml

checkCIF report


Comment top

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).

Related literature top

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 top

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%.

Refinement top

The C-bound H atoms were placed in calculated positions with C—H = 0.93–0.97 Å and allowed to ride on their parent atoms with Uiso(H) = 1.2Ueq(C). The disordered O-bound H atoms with half occupancies were refined with the O—H and C···H distances restrained to 0.82 (1) Å and 1.85 (2) Å and with Uiso(H) = 1.5Ueq(O).

Structure description top

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).

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).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound with atom labelling scheme and thermal ellipsoids drawn at the 40% probability level. Intermolecular hydrogen bonds O—H···O are presented by dashed lines.
[Figure 2] Fig. 2. Portion of six infinite two-dimensional corrugated sheets in (I) linked by hydrogen-bonds, viewed along the a axis. These six sheets can be dubbed in three pairs of hydrogen-bonded layers.
1-(2-Hydroxyethyl)pyrrole-2,5-dione top
Crystal data top
C6H7NO3F(000) = 592.0
Mr = 141.13Dx = 1.424 Mg m−3
Monoclinic, P21/cMelting point: 344 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 7.734 (4) ÅCell parameters from 380 reflections
b = 9.701 (5) Åθ = 2.5–28.3°
c = 17.673 (8) ŵ = 0.12 mm−1
β = 96.660 (7)°T = 293 K
V = 1317.0 (11) Å3Block, colourless
Z = 80.45 × 0.29 × 0.26 mm
Data collection top
Bruker SMART CCD
diffractometer		3003 independent reflections
Radiation source: fine-focus sealed tube1972 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
φ and ω scansθmax = 28.4°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −8→10
Tmin = 0.962, Tmax = 0.976k = −11→12
7522 measured reflectionsl = −23→23
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.081Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.217H 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 parametersΔρmax = 0.38 e Å−3
8 restraintsΔρmin = −0.29 e Å−3
Crystal data top
C6H7NO3V = 1317.0 (11) Å3
Mr = 141.13Z = 8
Monoclinic, P21/cMo Kα radiation
a = 7.734 (4) ŵ = 0.12 mm−1
b = 9.701 (5) ÅT = 293 K
c = 17.673 (8) Å0.45 × 0.29 × 0.26 mm
β = 96.660 (7)°
Data collection top
Bruker SMART CCD
diffractometer		3003 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		1972 reflections with I > 2σ(I)
Tmin = 0.962, Tmax = 0.976Rint = 0.060
7522 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0818 restraints
wR(F2) = 0.217H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.38 e Å−3
3003 reflectionsΔρmin = −0.29 e Å−3
201 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O2A0.2520 (4)1.0076 (3)0.5604 (2)0.0911 (10)
O5A0.2601 (3)0.5693 (2)0.64576 (16)0.0653 (7)
O12A0.4289 (3)0.6222 (3)0.47672 (15)0.0617 (7)
H12A0.3228 (14)0.630 (4)0.475 (5)0.093*0.50
H12B0.1884 (13)0.594 (5)0.452 (5)0.093*0.50
O2B0.2505 (3)0.9305 (2)0.33843 (17)0.0709 (8)
O5B0.2400 (3)0.4751 (2)0.28146 (15)0.0622 (7)
O12B0.0831 (3)0.5827 (2)0.45141 (14)0.0529 (6)
H12C0.450 (9)0.561 (3)0.508 (2)0.079*0.50
H12D0.023 (5)0.548 (6)0.481 (4)0.079*0.50
N1A0.3035 (3)0.7840 (2)0.59889 (14)0.0440 (6)
N1B0.1968 (3)0.7013 (2)0.31464 (13)0.0369 (6)
C2A0.2026 (5)0.9003 (3)0.5835 (2)0.0544 (8)
C3A0.0255 (5)0.8636 (4)0.6022 (2)0.0607 (9)
H3A−0.07080.92160.59730.073*
C4A0.0275 (4)0.7364 (4)0.62661 (18)0.0527 (8)
H4A−0.06690.68880.64200.063*
C5A0.2058 (4)0.6808 (3)0.62565 (17)0.0435 (7)
C11A0.4858 (4)0.7719 (3)0.5876 (2)0.0510 (8)
H1110.53800.69720.61890.061*
H1120.54580.85640.60400.061*
C12A0.5090 (4)0.7447 (4)0.5057 (2)0.0583 (9)
H1210.46120.82160.47510.070*
H1220.63250.73980.50090.070*
C2B0.2981 (4)0.8183 (3)0.32075 (18)0.0436 (7)
C3B0.4715 (4)0.7761 (3)0.30062 (19)0.0483 (8)
H3B0.56710.83400.29970.058*
C4B0.4683 (4)0.6462 (3)0.28466 (18)0.0468 (8)
H4B0.56130.59570.27020.056*
C5B0.2936 (4)0.5904 (3)0.29288 (17)0.0412 (7)
C11B0.0143 (4)0.6925 (3)0.32856 (17)0.0432 (7)
H113−0.03590.60870.30550.052*
H114−0.04890.77000.30410.052*
C12B−0.0084 (4)0.6927 (3)0.41195 (19)0.0491 (8)
H1230.03320.77950.43430.059*
H124−0.13130.68500.41770.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O2A0.089 (2)0.0435 (16)0.144 (3)0.0012 (14)0.0289 (19)0.0214 (17)
O5A0.0582 (15)0.0482 (14)0.0865 (19)−0.0029 (11)−0.0048 (13)0.0229 (13)
O12A0.0487 (13)0.0734 (17)0.0628 (16)0.0004 (12)0.0055 (12)−0.0066 (12)
O2B0.0717 (17)0.0406 (14)0.105 (2)0.0016 (11)0.0321 (15)−0.0125 (13)
O5B0.0615 (15)0.0379 (13)0.0905 (19)−0.0007 (10)0.0232 (13)−0.0092 (12)
O12B0.0448 (12)0.0588 (14)0.0561 (14)−0.0039 (11)0.0105 (11)0.0157 (11)
N1A0.0459 (14)0.0391 (14)0.0468 (14)−0.0010 (11)0.0048 (11)0.0041 (11)
N1B0.0362 (12)0.0353 (13)0.0407 (13)0.0040 (10)0.0109 (10)0.0037 (10)
C2A0.066 (2)0.0370 (18)0.060 (2)0.0050 (15)0.0101 (17)0.0021 (15)
C3A0.060 (2)0.053 (2)0.072 (2)0.0157 (16)0.0204 (18)−0.0029 (18)
C4A0.0535 (19)0.061 (2)0.0456 (18)−0.0009 (16)0.0136 (15)−0.0041 (15)
C5A0.0464 (17)0.0445 (17)0.0388 (15)−0.0010 (13)0.0011 (12)0.0060 (13)
C11A0.0379 (16)0.0485 (18)0.065 (2)−0.0061 (14)0.0005 (14)−0.0005 (16)
C12A0.0439 (18)0.062 (2)0.071 (2)−0.0044 (16)0.0140 (16)0.0094 (18)
C2B0.0481 (17)0.0371 (16)0.0468 (17)0.0009 (13)0.0109 (13)0.0052 (13)
C3B0.0433 (17)0.0446 (18)0.0588 (19)−0.0076 (13)0.0133 (14)0.0083 (15)
C4B0.0428 (17)0.0435 (17)0.0567 (19)0.0110 (13)0.0170 (14)0.0131 (14)
C5B0.0479 (17)0.0338 (16)0.0427 (16)0.0073 (12)0.0089 (13)0.0064 (12)
C11B0.0368 (15)0.0454 (17)0.0484 (17)0.0037 (12)0.0092 (13)0.0045 (13)
C12B0.0490 (18)0.0458 (18)0.0565 (19)0.0015 (14)0.0227 (15)0.0005 (15)
Geometric parameters (Å, º) top
O2A—C2A1.196 (4)C3A—H3A0.9300
O5A—C5A1.199 (4)C4A—C5A1.483 (4)
O12A—C12A1.409 (4)C4A—H4A0.9300
O12A—H12A0.821 (10)C11A—C12A1.503 (5)
O12A—H12C0.821 (10)C11A—H1110.9700
O2B—C2B1.202 (4)C11A—H1120.9700
O5B—C5B1.201 (4)C12A—H1210.9700
O12B—C12B1.418 (4)C12A—H1220.9700
O12B—H12B0.821 (10)C2B—C3B1.484 (4)
O12B—H12D0.817 (10)C3B—C4B1.291 (4)
N1A—C5A1.371 (4)C3B—H3B0.9300
N1A—C2A1.381 (4)C4B—C5B1.478 (4)
N1A—C11A1.452 (4)C4B—H4B0.9300
N1B—C2B1.376 (4)C11B—C12B1.504 (4)
N1B—C5B1.391 (4)C11B—H1130.9700
N1B—C11B1.463 (4)C11B—H1140.9700
C2A—C3A1.489 (5)C12B—H1230.9700
C3A—C4A1.307 (5)C12B—H1240.9700
C12A—O12A—H12A110 (2)O12A—C12A—C11A113.7 (3)
C12A—O12A—H12C109 (2)O12A—C12A—H121108.8
H12A—O12A—H12C102 (8)C11A—C12A—H121108.8
C12B—O12B—H12B110 (2)O12A—C12A—H122108.8
C12B—O12B—H12D110 (2)C11A—C12A—H122108.8
H12B—O12B—H12D133 (6)H121—C12A—H122107.7
C5A—N1A—C2A110.1 (3)O2B—C2B—N1B125.3 (3)
C5A—N1A—C11A124.8 (3)O2B—C2B—C3B128.6 (3)
C2A—N1A—C11A125.1 (3)N1B—C2B—C3B106.0 (2)
C2B—N1B—C5B109.9 (2)C4B—C3B—C2B109.1 (3)
C2B—N1B—C11B125.9 (2)C4B—C3B—H3B125.5
C5B—N1B—C11B124.2 (2)C2B—C3B—H3B125.5
O2A—C2A—N1A125.6 (3)C3B—C4B—C5B109.3 (3)
O2A—C2A—C3A128.5 (3)C3B—C4B—H4B125.3
N1A—C2A—C3A105.9 (3)C5B—C4B—H4B125.3
C4A—C3A—C2A108.9 (3)O5B—C5B—N1B125.5 (3)
C4A—C3A—H3A125.6O5B—C5B—C4B128.7 (3)
C2A—C3A—H3A125.6N1B—C5B—C4B105.7 (2)
C3A—C4A—C5A108.4 (3)N1B—C11B—C12B112.9 (3)
C3A—C4A—H4A125.8N1B—C11B—H113109.0
C5A—C4A—H4A125.8C12B—C11B—H113109.0
O5A—C5A—N1A125.0 (3)N1B—C11B—H114109.0
O5A—C5A—C4A128.2 (3)C12B—C11B—H114109.0
N1A—C5A—C4A106.8 (3)H113—C11B—H114107.8
N1A—C11A—C12A111.9 (3)O12B—C12B—C11B111.9 (2)
N1A—C11A—H111109.2O12B—C12B—H123109.2
C12A—C11A—H111109.2C11B—C12B—H123109.2
N1A—C11A—H112109.2O12B—C12B—H124109.2
C12A—C11A—H112109.2C11B—C12B—H124109.2
H111—C11A—H112107.9H123—C12B—H124107.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12A—H12A···O12B0.82 (1)1.91 (1)2.688 (3)158 (3)
O12B—H12B···O12A0.82 (1)1.88 (2)2.688 (3)168 (8)
O12A—H12C···O12Ai0.82 (1)2.01 (4)2.702 (5)142 (7)
O12B—H12D···O12Bii0.82 (1)1.98 (2)2.773 (4)163 (5)
C4B—H4B···O5Ai0.932.493.114 (4)125
C3A—H3A···O2Biii0.932.383.188 (4)146
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formulaC6H7NO3
Mr141.13
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)7.734 (4), 9.701 (5), 17.673 (8)
β (°) 96.660 (7)
V (Å3)1317.0 (11)
Z8
Radiation typeMo Kα
µ (mm−1)0.12
Crystal size (mm)0.45 × 0.29 × 0.26
Data collection
DiffractometerBruker SMART CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.962, 0.976
No. of measured, independent and
observed [I > 2σ(I)] reflections		7522, 3003, 1972
Rint0.060
(sin θ/λ)max (Å−1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.081, 0.217, 1.10
No. of reflections3003
No. of parameters201
No. of restraints8
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.38, −0.29

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12A—H12A···O12B0.821 (10)1.908 (13)2.688 (3)158 (3)
O12B—H12B···O12A0.821 (10)1.88 (2)2.688 (3)168 (8)
O12A—H12C···O12Ai0.821 (10)2.01 (4)2.702 (5)142 (7)
O12B—H12D···O12Bii0.817 (10)1.980 (16)2.773 (4)163 (5)
C4B—H4B···O5Ai0.932.493.114 (4)124.7
C3A—H3A···O2Biii0.932.383.188 (4)145.9
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) −x, −y+2, −z+1.
 

Acknowledgements

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).

References

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ISSN: 2056-9890
Volume 68| Part 4| April 2012| Page o970
doi:10.1107/S1600536812008938
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