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

Archana, R.; Yamuna, E.; Rajendra Prasad, K.J.; Thiruvalluvar, A.; Butcher, R.J.

doi:10.1107/S1600536810041772

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 (C-C) = 0.003 Å
R = 0.045
wR = 0.129
Data-to-parameter ratio = 8.5
Details

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

R. Archana,^a E. Yamuna,^b K. J. Rajendra Prasad,^b A. Thiruvalluvar ^a ^* and R. J. Butcher ^c

^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-HO hydrogen bonds are found.

Related literature

For the importance of the indole nucleus, see: Satoshi & Tominari (2001). For the synthesis of fused cyclohept[b]indole derivatives, see: Butin et al. (2010); Fujimori & Yamane (1978); Wahlström et al. (2007). For heteroannulated cyclohept[b]indole derivatives, see: Kavitha & Prasad (1999, 2001). For crystallographic studies of cyclohept[b]indoles, see: Sridharan et al. (2008a,b, 2009); Yamuna et al. (2010).

Experimental

Crystal data

C₁₅H₁₇NO
M_r = 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 radiation
= 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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.887, T_max = 1.000
1327 measured reflections
1327 independent reflections
1285 reflections with I > 2(I)

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.129
S = 1.09
1327 reflections
156 parameters
1 restraint
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C10-H10BO6ⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); 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.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Fujimori, K. & Yamane, K. (1978). Bull. Chem. Soc. Jpn, 51, 3579-3581.
Kavitha, C. & Prasad, K. J. R. (1999). Heterocycl. Commun. 5, 481-488.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Sridharan, M., Prasad, K. J. R., Gunaseelan, A. T., Thiruvalluvar, A. & Butcher, R. J. (2008a). Acta Cryst. E64, o1697.
Sridharan, M., Prasad, K. J. R., Ngendahimana, A. & Zeller, M. (2008b). Acta Cryst. E64, o1207.
Sridharan, M., Rajendra Prasad, K. J., Thomas Gunaseelan, A., Thiruvalluvar, A. & Butcher, R. J. (2009). Acta Cryst. E65, o698.
Wahlström, N., Slatt, J., Stensland, B., Ertan, A., Bergman, J. & Janosik, T. (2007). J. Org. Chem. 72, 5886-5889.
Yamuna, E., Sridharan, M., Prasad, K. J. R. & Zeller, M. (2010). J. Chem. Crystallogr. 40, 402-411.

organic compounds