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Volume 66 
Part 11 
Page o2882  
November 2010  

Received 5 October 2010
Accepted 15 October 2010
Online 23 October 2010

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.045
wR = 0.129
Data-to-parameter ratio = 8.5
Details
Open access

2,5-Dimethyl-7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-one

aPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India,bDepartment of Chemistry, Bharathiar University, Coimbatore 641 046, Tamilnadu, India, and cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
Correspondence e-mail: thiruvalluvar.a@gmail.com

In the title molecule, C15H17NO, the dihedral angle between the benzene and pyrrole rings is 1.45 (13)°. The cycloheptene ring adopts a slightly distorted boat conformation. In the crystal structure, intermolecular C-H...O hydrogen bonds are found.

Related literature

For the importance of the indole nucleus, see: Satoshi & Tominari (2001[Satoshi, H. & Tominari, C. (2001). Nat. Prod. Rep. 18, 66-87.]). For the synthesis of fused cyclohept[b]indole derivatives, see: Butin et al. (2010[Butin, A. V., Kostyukova, N. O., Tsiunchik, F. A., Lysenko, S. A. & Trushkov, I. V. (2010). Chem. Heterocycl. Compd, 46, 117-119.]); Fujimori & Yamane (1978[Fujimori, K. & Yamane, K. (1978). Bull. Chem. Soc. Jpn, 51, 3579-3581.]); Wahlström et al. (2007[Wahlström, N., Slatt, J., Stensland, B., Ertan, A., Bergman, J. & Janosik, T. (2007). J. Org. Chem. 72, 5886-5889.]). For heteroannulated cyclohept[b]indole derivatives, see: Kavitha & Prasad (1999[Kavitha, C. & Prasad, K. J. R. (1999). Heterocycl. Commun. 5, 481-488.], 2001[Kavitha, C. & Prasad, K. J. R. (2001). Indian J. Chem. Sect. B, 40, 601-602.]). For crystallographic studies of cyclohept[b]indoles, see: Sridharan et al. (2008a[Sridharan, M., Prasad, K. J. R., Gunaseelan, A. T., Thiruvalluvar, A. & Butcher, R. J. (2008a). Acta Cryst. E64, o1697.],b[Sridharan, M., Prasad, K. J. R., Ngendahimana, A. & Zeller, M. (2008b). Acta Cryst. E64, o1207.], 2009[Sridharan, M., Rajendra Prasad, K. J., Thomas Gunaseelan, A., Thiruvalluvar, A. & Butcher, R. J. (2009). Acta Cryst. E65, o698.]); Yamuna et al. (2010[Yamuna, E., Sridharan, M., Prasad, K. J. R. & Zeller, M. (2010). J. Chem. Crystallogr. 40, 402-411.]).

[Scheme 1]

Experimental

Crystal data
  • C15H17NO

  • Mr = 227.30

  • Orthorhombic, P c a 21

  • a = 15.5889 (3) Å

  • b = 10.5707 (2) Å

  • c = 7.5388 (2) Å

  • V = 1242.29 (5) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.59 mm-1

  • T = 295 K

  • 0.49 × 0.32 × 0.12 mm

Data collection
  • Oxford Diffraction Xcalibur Ruby Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.887, Tmax = 1.000

  • 1327 measured reflections

  • 1327 independent reflections

  • 1285 reflections with I > 2[sigma](I)

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.129

  • S = 1.09

  • 1327 reflections

  • 156 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C10-H10B...O6i 0.97 2.59 3.550 (3) 168
Symmetry code: (i) [x+{\script{1\over 2}}, -y+1, z].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2724 ).


Acknowledgements

RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

Butin, A. V., Kostyukova, N. O., Tsiunchik, F. A., Lysenko, S. A. & Trushkov, I. V. (2010). Chem. Heterocycl. Compd, 46, 117-119.  [ISI] [CrossRef] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Fujimori, K. & Yamane, K. (1978). Bull. Chem. Soc. Jpn, 51, 3579-3581.  [CrossRef] [ChemPort] [ISI]
Kavitha, C. & Prasad, K. J. R. (1999). Heterocycl. Commun. 5, 481-488.  [ChemPort]
Kavitha, C. & Prasad, K. J. R. (2001). Indian J. Chem. Sect. B, 40, 601-602.
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.
Satoshi, H. & Tominari, C. (2001). Nat. Prod. Rep. 18, 66-87.  [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Sridharan, M., Prasad, K. J. R., Gunaseelan, A. T., Thiruvalluvar, A. & Butcher, R. J. (2008a). Acta Cryst. E64, o1697.  [CSD] [CrossRef] [details]
Sridharan, M., Prasad, K. J. R., Ngendahimana, A. & Zeller, M. (2008b). Acta Cryst. E64, o1207.  [CSD] [CrossRef] [details]
Sridharan, M., Rajendra Prasad, K. J., Thomas Gunaseelan, A., Thiruvalluvar, A. & Butcher, R. J. (2009). Acta Cryst. E65, o698.  [CSD] [CrossRef] [details]
Wahlström, N., Slatt, J., Stensland, B., Ertan, A., Bergman, J. & Janosik, T. (2007). J. Org. Chem. 72, 5886-5889.  [PubMed]
Yamuna, E., Sridharan, M., Prasad, K. J. R. & Zeller, M. (2010). J. Chem. Crystallogr. 40, 402-411.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2010). E66, o2882  [ doi:10.1107/S1600536810041772 ]

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