4,8-Dimethyl­pyrano[2,3-a]carbazol-2(11H)-one

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

doi:10.1107/S1600536809009854

Volume 65
Part 4
Page o830
April 2009

Received 15 March 2009
Accepted 17 March 2009
Online 25 March 2009

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.002 Å
R = 0.044
wR = 0.132
Data-to-parameter ratio = 14.5
Details

4,8-Dimethylpyrano[2,3-a]carbazol-2(11H)-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

The molecule of the title compound, C₁₇H₁₃NO₂, is nearly planar, the r.m.s. deviation for all non-H atoms excluding the two methyl C atoms being 0.089 Å. Intermolecular N-HO and C-HO hydrogen bonds are found in the crystal structure. C-H [pi] interactions are also found. The H atoms of the methyl group attached to the benzene ring are disordered equally over two positions.

Related literature

For the synthesis of 2-methyl- and 2-phenyl-pyrano[2,3-a]carbazol-4-ones and their derivatives, see: Kavitha & Rajendra Prasad (2003). For related crystal structures, see: Sridharan et al. (2007); Sridharan et al. (2008a,b); Sridharan et al. (2008).

Experimental

Crystal data

C₁₇H₁₃NO₂
M_r = 263.28
Monoclinic, C 2/c
a = 26.8502 (4) Å
b = 6.8202 (1) Å
c = 15.8265 (3) Å
= 115.531 (2)°
V = 2615.21 (9) Å³
Z = 8
Cu K radiation
= 0.71 mm^-1
T = 295 K
0.48 × 0.45 × 0.18 mm

Data collection

Oxford Diffraction Gemini R diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.313, T_max = 1.000 (expected range = 0.276-0.880)
6122 measured reflections
2703 independent reflections
2218 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.132
S = 1.07
2703 reflections
186 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.22 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N11-H11O2ⁱ	0.86 (2)	2.01 (2)	2.814 (2)	154.5 (19)
C14-H14BO2ⁱⁱ	0.96	2.39	3.338 (2)	168
C6-H6Cg1ⁱⁱⁱ	0.93	2.90	3.389 (1)	114
C5-H5Cg2ⁱⁱⁱ	0.93	2.98	3.626 (1)	128
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z]$ ; (ii) x, y-1, z; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 is the centroid of the pyrrole ring and Cg2 is the centroid of the C6B-C10A ring.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2315 ).

Acknowledgements

We acknowledge the UGC, New Delhi, India, for the award of Major Research Project grant No. F.No.31-122/2005. MS thanks the UGC, New Delhi, India, for the award of a research fellowship. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Kavitha, C. & Rajendra Prasad, K. J. (2003). J. Chem. Res. (M), pp. 1025-1036.
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Sridharan, M., Prasad, K. J. R., Ngendahimana, A. & Zeller, M. (2008a). Acta Cryst. E64, o2155.
Sridharan, M., Prasad, K. J. R., Ngendahimana, A. & Zeller, M. (2008b). Acta Cryst. E64, o2157.
Sridharan, M., Prasad, K. J. R. & Zeller, M. (2007). Acta Cryst. E63, o4344.
Sridharan, M., Prasad, K. J. R. & Zeller, M. (2008). Acta Cryst. E64, o2156.

organic compounds