7,8,9,10-Tetra­hydro­cyclo­hepta­[b]indol-6(5H)-one

Sridharan, M.; Prasad, K.J.R.; Gunaseelan, A.T.; Thiruvalluvar, A.; Butcher, R.J.

doi:10.1107/S160053680802463X

Volume 64
Part 9
Page o1697
September 2008

Received 30 July 2008
Accepted 31 July 2008
Online 6 August 2008

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.001 Å
R = 0.053
wR = 0.145
Data-to-parameter ratio = 29.5
Details

7,8,9,10-Tetrahydrocyclohepta[b]indol-6(5H)-one

M. Sridharan,^a K. J. Rajendra Prasad,^a A. Thomas Gunaseelan,^b A. Thiruvalluvar ^b ^* and R. J. Butcher ^c

^aDepartment of Chemistry, Bharathiar University, Coimbatore 641 046, Tamilnadu, India,^bPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, and ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
Correspondence e-mail: athiru@vsnl.net

In the title molecule, C₁₃H₁₃NO, the dihedral angle between the benzene and pyrrole rings is 1.05 (5)°. The cycloheptene ring adopts a slightly distorted boat conformation. In the crystal structure, intermolecular N-HO hydrogen bonds form centrosymmetric dimers. A C-H [pi] interaction, involving the benzene ring, is also found in the structure.

Related literature

For a related structure, see: Sridharan et al. (2008).

Experimental

Crystal data

C₁₃H₁₃NO
M_r = 199.24
Monoclinic, P 2₁ /c
a = 14.0914 (4) Å
b = 8.0883 (2) Å
c = 9.2503 (3) Å
= 108.937 (3)°
V = 997.24 (5) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 200 (2) K
0.56 × 0.38 × 0.31 mm

Data collection

Oxford Diffraction Gemini R diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.985, T_max = 1.000 (expected range = 0.960-0.974)
15925 measured reflections
4127 independent reflections
3036 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.145
S = 1.01
4127 reflections
140 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.31 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N5-H5O6ⁱ	0.891 (16)	1.976 (16)	2.8188 (11)	157.3 (13)
C10-H10ACgⁱⁱ	0.99	2.90	3.7087 (10)	139
Symmetry codes: (i) -x, -y, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ . Cg is the centroid of the benzene ring.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2274 ).

Acknowledgements

MS thanks the UGC, New Delhi, India, for the award of a research fellowship. KJR acknowledges the UGC, New Delhi, India, for the award of Major Research Project Grant No. F.No.31-122/2005. AT thanks the UGC, India, for the award of a Minor Research Project [File No. MRP-2355/06(UGC-SERO), Link No. 2355, 10/01/2007]. RJB acknowledges the NSF-MRI program for funding to purchase the X-ray CCD diffractometer.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Sridharan, M., Prasad, K. J. R., Ngendahimana, A. & Zeller, M. (2008). Acta Cryst. E64, o1207.

organic compounds