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Volume 69 
Part 8 
Page o1312  
August 2013  

Received 21 June 2013
Accepted 18 July 2013
Online 24 July 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.032
wR = 0.089
Data-to-parameter ratio = 13.9
Details
Open access

2-Hydroxyisoquinoline-1,3(2H,4H)-dione

aSchool of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan
Correspondence e-mail: ishi206@u-shizuoka-ken.ac.jp

The title molecule, C9H7NO3, exists in the diketo form and the isoquinoline unit is approximately planar (r.m.s. deviation = 0.0158 Å). In the crystal, molecules are linked into inversion dimers through pairs of O-H...O hydrogen bonds and are further assembled into the (100) layers via stacking interactions [centroid-centroid distances = 3.460 (3) and 3.635 (4) Å].

Related literature

For the biological properties of the title compound, see: Parkes et al. (2003[Parkes, K. E., Ermert, P., Fässler, J., Ives, J., Martin, J. A., Merrett, J. H., Obrecht, D., Williams, G. & Klumpp, K. (2003). J. Med. Chem. 46, 1153-1164.]); Hang et al. (2004[Hang, J. Q., Rajendran, S., Yang, Y., Li, Y., In, P. W., Overton, H., Parkes, K. E., Cammack, N., Martin, J. A. & Klumpp, K. (2004). Biochem. Biophys. Res. Commun. 317, 321-329.]); Billamboz et al. (2008[Billamboz, M., Bailly, F., Barreca, M. L., De Luca, L., Mouscadet, J. F., Calmels, C., Andréola, M. L., Witvrouw, M., Christ, F., Debyser, Z. & Cotelle, P. (2008). J. Med. Chem. 51, 7717-7730.]). For a related structure, see: Miao et al. (1995[Miao, F.-M., Wang, J.-L. & Miao, X.-S. (1995). Acta Cryst. C51, 712-713.]).

[Scheme 1]

Experimental

Crystal data
  • C9H7NO3

  • Mr = 177.16

  • Monoclinic, P 21 /n

  • a = 12.336 (5) Å

  • b = 8.666 (4) Å

  • c = 7.052 (7) Å

  • [beta] = 104.19 (5)°

  • V = 730.8 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 100 K

  • 0.50 × 0.50 × 0.45 mm

Data collection
  • Rigaku AFC-7R diffractometer

  • 3873 measured reflections

  • 1650 independent reflections

  • 1484 reflections with F2 > 2[sigma](F2)

  • Rint = 0.016

  • 3 standard reflections every 150 reflections intensity decay: -0.5%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.089

  • S = 1.04

  • 1650 reflections

  • 119 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O5-H5...O1i 0.84 1.91 2.7056 (17) 158
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999[Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.]); cell refinement: WinAFC Diffractometer Control Software; data reduction: WinAFC Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (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: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); software used to prepare material for publication: CrystalStructure.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2583 ).


Acknowledgements

The authors acknowledge the University of Shizuoka for supporting this study.

References

Billamboz, M., Bailly, F., Barreca, M. L., De Luca, L., Mouscadet, J. F., Calmels, C., Andréola, M. L., Witvrouw, M., Christ, F., Debyser, Z. & Cotelle, P. (2008). J. Med. Chem. 51, 7717-7730.  [CrossRef] [PubMed] [ChemPort]
Hang, J. Q., Rajendran, S., Yang, Y., Li, Y., In, P. W., Overton, H., Parkes, K. E., Cammack, N., Martin, J. A. & Klumpp, K. (2004). Biochem. Biophys. Res. Commun. 317, 321-329.  [CrossRef] [PubMed] [ChemPort]
Miao, F.-M., Wang, J.-L. & Miao, X.-S. (1995). Acta Cryst. C51, 712-713.  [CrossRef] [IUCr Journals]
Parkes, K. E., Ermert, P., Fässler, J., Ives, J., Martin, J. A., Merrett, J. H., Obrecht, D., Williams, G. & Klumpp, K. (2003). J. Med. Chem. 46, 1153-1164.  [CrossRef] [PubMed] [ChemPort]
Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1312  [ doi:10.1107/S1600536813019843 ]

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