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Volume 69 
Part 8 
Page o1311  
August 2013  

Received 25 June 2013
Accepted 19 July 2013
Online 24 July 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.010 Å
R = 0.069
wR = 0.212
Data-to-parameter ratio = 9.6
Details
Open access

2-(Benzyloxy)isoquinoline-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 compound, C16H13NO3, exists in the keto form and the isoquinoline system is essentially planar (mean deviation = 0.0424 Å). The dihedral angle between the aromatic rings is 4.2 (2)°. In the crystal, molecules are linked via weak C-H...O hydrogen bonds and C-H...[pi] interactions, forming a three-dimensional structure.

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.]); Sun et al. (2005[Sun, W., Pertzev, A. & Nicholson, A. W. (2005). Nucleic Acids Res. 33, 807-815.]); 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 related structures, see: Ishikawa & Matsuo (2013[Ishikawa, Y. & Matsuo, S. (2013). Acta Cryst. E69, o1312.]); Lee et al. (2008[Lee, J. M., Park, E. J., Cho, S. H. & Chang, S. (2008). J. Am. Chem. Soc. 130, 7824-7825.]).

[Scheme 1]

Experimental

Crystal data
  • C16H13NO3

  • Mr = 267.28

  • Orthorhombic, P n a 21

  • a = 7.677 (4) Å

  • b = 12.003 (10) Å

  • c = 13.885 (10) Å

  • V = 1279.4 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.50 × 0.18 × 0.13 mm

Data collection
  • Rigaku AFC-7R diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.262, Tmax = 0.988

  • 2451 measured reflections

  • 1756 independent reflections

  • 1191 reflections with F2 > 2[sigma](F2)

  • Rint = 0.081

  • 3 standard reflections every 150 reflections intensity decay: 1.0%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.069

  • wR(F2) = 0.212

  • S = 1.03

  • 1756 reflections

  • 182 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C4-C8 and C11-C16 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C6-H25...O19i 0.95 2.51 3.334 (8) 146
C3-H22B...Cg3ii 0.99 2.91 3.556 (7) 124
C7-H26...Cg2iii 0.95 2.88 3.470 (8) 122
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+1, -y+1, z+{\script{1\over 2}}]; (iii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z].

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: ZL2556 ).


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]
Ishikawa, Y. & Matsuo, S. (2013). Acta Cryst. E69, o1312.  [CrossRef] [IUCr Journals]
Lee, J. M., Park, E. J., Cho, S. H. & Chang, S. (2008). J. Am. Chem. Soc. 130, 7824-7825.  [CrossRef] [PubMed] [ChemPort]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [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]
Sun, W., Pertzev, A. & Nicholson, A. W. (2005). Nucleic Acids Res. 33, 807-815.  [Web of Science] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1311  [ doi:10.1107/S1600536813019934 ]

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