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Volume 67 
Part 6 
Pages o1519-o1520  
June 2011  

Received 10 May 2011
Accepted 19 May 2011
Online 25 May 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.001 Å
R = 0.039
wR = 0.113
Data-to-parameter ratio = 26.0
Details
Open access

Methyl 4'-isobutyl-2,2'-dimethyl-1,3-dioxo-2,3-dihydro-1H,4'H-spiro[isoquinoline-4,5'-oxazole]-4'-carboxylate

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, People's Republic of China
Correspondence e-mail: hkfun@usm.my

In the isoquinoline ring system of the title molecule, C19H22N2O5, the N-heterocyclic ring is in a half-boat conformation. The dioxa-2-azaspiro ring is essentially planar [maximum deviation = 0.042 (1) Å] and forms a dihedral angle of 81.85 (4)° with the benzene ring. In the crystal, the molecules are linked via intermolecular C-H...O hydrogen bonds into chains along [010].

Related literature

For general background to and the potential biological activity of the title compound, see: Pollers-Wieers et al. (1981[Pollers-Wieers, C., Vekemans, J., Toppet, S. & Hoornaert, G. (1981). Tetrahedron 37, 4321-4326.]); Malamas et al. (1994[Malamas, M. S., Hohman, T. C. & Millen, J. (1994). J. Med. Chem. 37, 2043-2058.]); Yu et al. (2010[Yu, H., Li, J., Kou, Z., Du, X., Wei, Y., Fun, H.-K., Xu, J. & Zhang, Y. (2010). J. Org. Chem. 75, 2989-3001.]); Mitchell et al. (1995[Mitchell, G., Clarke, E. D., Ridley, S. M., Greenhow, D. T., Gillen, K. J., Vohra, S. K. & Wardman, P. (1995). Pestic. Sci. 44, 49-58.], 2000[Mitchell, G., Clarke, E. D., Ridley, S. M., Bartlett, D. W., Gillen, K. J., Vohra, S. K., Greenhow, D. T., Ormrod, J. C. & Wardman, P. (2000). Pest. Manag. Sci. 56, 120-126.]); Badillo et al. (2010[Badillo, J. J., Hanhan, N. V. & Franz, A. K. (2010). Curr. Opin. Drug Discovery Dev. 13, 758-766.]); Wang et al. (2010[Wang, L., Huang, Y. C., Liu, Y., Fun, H.-K., Zhang, Y. & Xu, J. H. (2010). J. Org. Chem. 75, 7757-7768.]); Nair et al. (2002[Nair, V., Sethumadhavan, D., Nair, S. M., Viji, S. & Rath, P. (2002). Tetrahedron, 58, 3003-3007.]); Huang et al. (2011[Huang, C., Yu, H., Miao, Z., Zhou, J., Wang, S., Fun, H.-K., Xu, J. & Zhang, Y. (2011). Org. Biomol. Chem. 9, 3629-3631.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]). For standard bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For related structures, see: Fun et al. (2011a[Fun, H.-K., Quah, C. K., Huang, C. & Yu, H. (2011a). Acta Cryst. E67, o1271-o1272.],b[Fun, H.-K., Quah, C. K., Huang, C. & Yu, H. (2011b). Acta Cryst. E67, o1273-o1274.],c[Fun, H.-K., Quah, C. K., Huang, C. & Yu, H. (2011c). Acta Cryst. E67, o1311-o1312.],d[Fun, H.-K., Quah, C. K., Huang, C. & Yu, H. (2011d). Acta Cryst. E67, o1340-o1341.]).

[Scheme 1]

Experimental

Crystal data
  • C19H22N2O5

  • Mr = 358.39

  • Triclinic, [P \overline 1]

  • a = 8.6764 (1) Å

  • b = 8.9366 (1) Å

  • c = 12.0684 (2) Å

  • [alpha] = 93.495 (1)°

  • [beta] = 109.892 (1)°

  • [gamma] = 98.426 (1)°

  • V = 864.22 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.40 × 0.29 × 0.18 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.961, Tmax = 0.982

  • 25638 measured reflections

  • 6231 independent reflections

  • 5381 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.113

  • S = 1.05

  • 6231 reflections

  • 240 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.46 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2A...O4i 0.93 2.56 3.4353 (11) 158
C4-H4A...O2ii 0.93 2.56 3.2878 (11) 136
C12-H12C...O4i 0.96 2.59 3.3600 (11) 138
Symmetry codes: (i) -x+2, -y, -z; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, 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: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2597 ).


Acknowledgements

HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160). Financial support from the Program for New Century Excellent Talents in Universities (NCET-08-0271) of China is also acknowledged.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Badillo, J. J., Hanhan, N. V. & Franz, A. K. (2010). Curr. Opin. Drug Discovery Dev. 13, 758-766.  [ChemPort]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Fun, H.-K., Quah, C. K., Huang, C. & Yu, H. (2011a). Acta Cryst. E67, o1271-o1272.  [CrossRef] [ChemPort] [details]
Fun, H.-K., Quah, C. K., Huang, C. & Yu, H. (2011b). Acta Cryst. E67, o1273-o1274.  [CrossRef] [ChemPort] [details]
Fun, H.-K., Quah, C. K., Huang, C. & Yu, H. (2011c). Acta Cryst. E67, o1311-o1312.  [CrossRef] [details]
Fun, H.-K., Quah, C. K., Huang, C. & Yu, H. (2011d). Acta Cryst. E67, o1340-o1341.  [CrossRef] [details]
Huang, C., Yu, H., Miao, Z., Zhou, J., Wang, S., Fun, H.-K., Xu, J. & Zhang, Y. (2011). Org. Biomol. Chem. 9, 3629-3631.  [CSD] [CrossRef] [ChemPort] [PubMed]
Malamas, M. S., Hohman, T. C. & Millen, J. (1994). J. Med. Chem. 37, 2043-2058.  [CrossRef] [ChemPort] [PubMed] [ISI]
Mitchell, G., Clarke, E. D., Ridley, S. M., Bartlett, D. W., Gillen, K. J., Vohra, S. K., Greenhow, D. T., Ormrod, J. C. & Wardman, P. (2000). Pest. Manag. Sci. 56, 120-126.  [CrossRef] [ChemPort]
Mitchell, G., Clarke, E. D., Ridley, S. M., Greenhow, D. T., Gillen, K. J., Vohra, S. K. & Wardman, P. (1995). Pestic. Sci. 44, 49-58.  [CrossRef] [ChemPort]
Nair, V., Sethumadhavan, D., Nair, S. M., Viji, S. & Rath, P. (2002). Tetrahedron, 58, 3003-3007.  [ISI] [CSD] [CrossRef] [ChemPort]
Pollers-Wieers, C., Vekemans, J., Toppet, S. & Hoornaert, G. (1981). Tetrahedron 37, 4321-4326.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Wang, L., Huang, Y. C., Liu, Y., Fun, H.-K., Zhang, Y. & Xu, J. H. (2010). J. Org. Chem. 75, 7757-7768.  [CrossRef] [ChemPort]
Yu, H., Li, J., Kou, Z., Du, X., Wei, Y., Fun, H.-K., Xu, J. & Zhang, Y. (2010). J. Org. Chem. 75, 2989-3001.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2011). E67, o1519-o1520   [ doi:10.1107/S1600536811019003 ]

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