Methyl 9-methyl-1-oxo-2,3,4,9-tetra- hydro-1H-carbazole-2-carboxylate A. Thiruvalluvar, a * A. Thomas Gunaseelan, a A. Ebenezer Martin, b K. J. Rajendra Prasad b and R. J. Butcher c a PG Research Department of Physics, Rajah Serfoji Government College (Autono- mous), Thanjavur 613 005, Tamilnadu, India, b Department of Chemistry, Bharathiar University, Coimbatore 641 046, Tamilnadu, India, and c Department of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA Correspondence e-mail: athiru@vsnl.net Received 9 May 2007; accepted 30 May 2007 Key indicators: single-crystal X-ray study; T = 203 K; mean (C–C) = 0.003 A ˚ ; R factor = 0.067; wR factor = 0.177; data-to-parameter ratio = 21.0. The carbazole unit of the title molecule, C 15 H 15 NO 3 , is not planar. The dihedral angle between the benzene ring and the fused pyrrole ring is 0.9 (1) . The cyclohexene ring is in a half- chair form. The ester group has an equatorial orientation. In the crystal structure, the molecules are stabilized by inter- molecular C—HO hydrogen bonds. Related literature For related literature, see: Knolker & Reddy (2002); Guna- seelan et al. (2007a,b). Due to the interesting and important properties of carbazoles, a number of methodologies for the construction of the carbazole ring with other heterocyclic compounds have been reported (Knolker & Reddy, 2002). Gunaseelan et al. (2007a,b) have reported crystal structures of substituted carbazole derivatives, wherein the carbazole units are not planar. Experimental Crystal data C 15 H 15 NO 3 M r = 257.28 Monoclinic, P2 1 =a a = 9.1267 (3) A ˚ b = 8.2114 (3) A ˚ c = 17.2304 (9) A ˚ = 91.151 (4) V = 1291.04 (9) A ˚ 3 Z =4 Mo K radiation = 0.09 mm 1 T = 203 (2) K 0.67 0.35 0.32 mm Data collection Oxford Diffraction Gemini diffractometer Absorption correction: none 13753 measured reflections 3646 independent reflections 2639 reflections with I >2(I) R int = 0.038 Refinement R[F 2 >2(F 2 )] = 0.067 wR(F 2 ) = 0.177 S = 1.14 3646 reflections 174 parameters H-atom parameters constrained Á max = 0.35 e A ˚ 3 Á min = 0.18 e A ˚ 3 Table 1 Hydrogen-bond geometry (A ˚ , ). D—HA D—H HA DA D—HA C9—H9AO21 i 0.97 2.57 3.372 (3) 140 C22—H22BO1 ii 0.97 2.37 3.321 (3) 167 Symmetry codes: (i) x þ 1; y; z; (ii) x þ 1 2 ; y þ 1 2 ; z. Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003). 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]. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2018). References Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Gunaseelan, A. T., Thiruvalluvar, A., Martin, A. E. & Prasad, K. J. R. (2007a). Acta Cryst. E63, o2413–o2414. Gunaseelan, A. T., Thiruvalluvar, A., Martin, A. E. & Prasad, K. J. R. (2007b). Acta Cryst. E63, o2729–o2730. Knolker, H. J. & Reddy, K. R. (2002). Chem. Rev. 102, 4303–4427. Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Versions 1.171.32. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go ¨ttingen, Germany. Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. organic compounds Acta Cryst. (2007). E63, o3093 doi:10.1107/S160053680702644X # 2007 International Union of Crystallography o3093 Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368