Methyl 6′-amino-5′-cyano-2′-methyl-2-oxospiro­[indoline-3,4′-pyran]-3′-carboxyl­ate

Zhu, S.-L.; Liu, T.

doi:10.1107/S1600536810053274

Volume 67
Part 1
Page o238
January 2011

Received 17 November 2010
Accepted 18 December 2010
Online 24 December 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R = 0.045
wR = 0.127
Data-to-parameter ratio = 12.8
Details

Methyl 6'-amino-5'-cyano-2'-methyl-2-oxospiro[indoline-3,4'-pyran]-3'-carboxylate

Song-Lei Zhu ^a ^* and Ting Liu ^a

^aDepartment of Chemistry, Xuzhou Medical College, Xuzhou 221004, People's Republic of China
Correspondence e-mail: songleizhu@126.com

In the molecule of the title compound, C₁₆H₁₃N₃O₄, the atoms of the spiro pyran ring are nearly planar with a maximum deviation of 0.095 (2) Å. The indole and pyran rings are oriented at a dihedral angle of 87.3 (9)°. In the crystal, molecules are linked by intermolecular N-HN and N-HO hydrogen bonds.

Related literature

For the indole nucleus, see: Da-Silva et al. (2001). Compounds carrying the indole moiety exhibit antibacterial and fungicidal activity, see: Joshi & Chand (1982). Spirooxindole ring systems are found in a number of alkaloids like horsifiline, spirotryprostatin and elacomine, see: Abdel-Rahman et al. (2004). For our work on the preparation of heterocyclic compounds involving indole derivatives, see: Zhu et al. (2007).

Experimental

Crystal data

C₁₆H₁₃N₃O₄
M_r = 311.29
Monoclinic, P 2₁ /c
a = 15.0260 (15) Å
b = 10.0614 (11) Å
c = 10.4862 (12) Å
= 105.956 (1)°
V = 1524.3 (3) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 298 K
0.48 × 0.46 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.954, T_max = 0.971
7311 measured reflections
2686 independent reflections
1868 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.127
S = 1.04
2686 reflections
210 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N3ⁱ	0.86	2.09	2.928 (3)	165
N2-H2AO1ⁱⁱ	0.86	2.17	2.925 (2)	147
N2-H2BO1ⁱⁱⁱ	0.86	2.34	3.022 (2)	136
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z+1; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2334 ).

Acknowledgements

This work was partially supported by the Natural Science Foundation of Higher Education Institutions of Jiangsu Province (grant No. 09KJB150012) and the Special Presidential Foundation of Xuzhou Medical College (grant Nos. 09KJZ19 and 2010KJZ20) and the Open Foundation of the Key Laboratory of Cancer Biotherapy of Xuzhou Medical College (grant No. C0901).

References

Abdel-Rahman, A. H., Keshk, E. M., Hanna, M. A. & El-Bady, Sh. M. (2004). Bioorg. Med. Chem. 12, 2483-2488.
Bruker (2004). SAINT and SMART. Bruker AXS Inc., Madinson, Wisconsin, USA.
Da-Silva, J. F. M., Garden, S. J. & Pinto, A. C. (2001). J. Braz. Chem. Soc. 12, 273-324.
Joshi, K. C. & Chand, P. (1982). Pharmazie, 37, 1-12.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zhu, S. L., Ji, S. J. & Zhang, Y. (2007). Tetrahedron, 63, 9365-9372.

organic compounds