Spiro­[indene-1,1′-benzo[e]indolin]-2′-one

Chen, J.-X.; Wang, Y.-Q.; Liu, S.-W.; Lin, W.-E.; Chen, Z.-P.

doi:10.1107/S1600536810049809

Volume 67
Part 1
Page o9
January 2011

Received 28 October 2010
Accepted 29 November 2010
Online 4 December 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R = 0.074
wR = 0.199
Data-to-parameter ratio = 12.4
Details

Spiro[indene-1,1'-benzo[e]indolin]-2'-one

Jin-Xiang Chen,^a ^* Yu-Qin Wang,^a Shu-Wen Liu,^a Wei-Er Lin ^a and Zhi-Peng Chen ^a

^aSchool of Pharmaceutical Science, Southern Medical University, Guangzhou 510515, People's Republic of China
Correspondence e-mail: jxchen6281@gmail.com

In the title compound, C₂₀H₁₃NO, the indene ring is disordered over two sites with an occupancy ratio of 0.557 (2):0.443 (2). Both disordered components of indene are nearly perpendicular to the naphthalene ring system, making dihedral angles of 90.9 (2) and 85.0 (5)°. The five-membered ring of the 1H-pyrrol-2(3H)-one adopts an envelope conformation with the spiro C atom at the flap position. Intermolecular classical N-HO and weak C-HO hydrogen bonding is present in the crystal structure.

Related literature

For the biological activity of spiro lactams, see: Tsuda et al. (2004); Chen et al. (2005). For the synthesis of the title compound, see: Ready et al. (2004); Schoemaker & Speckamp (1978).

Experimental

Crystal data

C₂₀H₁₃NO
M_r = 283.31
Monoclinic, P 2₁ /c
a = 13.0150 (18) Å
b = 7.9180 (11) Å
c = 15.537 (2) Å
= 112.030 (2)°
V = 1484.2 (4) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 293 K
0.50 × 0.41 × 0.33 mm

Data collection

Rigaku Mercury diffractometer
6913 measured reflections
2526 independent reflections
1984 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.074
wR(F²) = 0.199
S = 1.06
2526 reflections
203 parameters
30 restraints
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO1ⁱ	0.86	1.99	2.815 (3)	162
C18-H18AO1ⁱⁱ	0.93	2.35	3.064 (5)	133
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2001); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5073 ).

Acknowledgements

This work was supported by the Medical Scientific Research Foundation of Guangdong Province (No. B107) and the Guangzhou Municipal Scientific and Technological Project, China (No. 2007 J1-C0251).

References

Chen, Z.-P., Tan, D.-M., Su, C.-Y. & Xu, Z.-L. (2005). Acta Cryst. E61, o1308-o1309.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Ready, J. M., Reisman, S. E. & Hirata, M. (2004). Angew. Chem. Int. Ed. 43, 1270-1273.
Rigaku/MSC (2001). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.
Rigaku/MSC, (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Schoemaker, H. E. & Speckamp, W. N. (1978). Tetrahedron Lett. 19, 1515-1518.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tsuda, M., Kasai, Y. & Komatsu, K. (2004). Org. Lett. 6, 3087-3089.

organic compounds