(E)-2-[(Furan-2-yl)methyl­idene]-7-methyl-2,3,4,9-tetra­hydro-1H-carbazol-1-one

Thiruvalluvar, A.; Archana, R.; Yamuna, E.; Rajendra Prasad, K.J.; Butcher, R.J.; Gupta, S.K.; Öztürk Yildirim, S.

doi:10.1107/S1600536812051203

Volume 69
Part 2
Page o150
February 2013

Received 17 December 2012
Accepted 18 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.002 Å
R = 0.047
wR = 0.132
Data-to-parameter ratio = 13.7
Details

(E)-2-[(Furan-2-yl)methylidene]-7-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one

A. Thiruvalluvar,^a ^* R. Archana,^a E. Yamuna,^b K. J. Rajendra Prasad,^b R. J. Butcher,^c Sushil K. Gupta ^d and Sema Öztürk Yildirim ^c,^e

^aPostgraduate Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India,^bDepartment of Chemistry, Bharathiar University, Coimbatore 641 046, Tamilnadu, India,^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA,^dSchool of Studies in Chemistry, Jiwaji University, Gwalior 474 011, MP, India, and ^eFaculty of Sciences, Department of Physics, Erciyes University, 38039 Kayseri, Turkey
Correspondence e-mail: thiruvalluvar.a@gmail.com

In the title molecule, C₁₈H₁₅NO₂, the atoms in the carbazole unit deviate from planarity [maximum deviation from mean plane = 0.1317 (12) Å]. The pyrrole ring makes dihedral angles of 1.01 (8) and 18.56 (10)° with the benzene and furan rings, respectively. The cyclohexene ring adopts a half-chair conformation. In the crystal, pairs of N-HO hydrogen bonds form an R₂²(10) ring. Molecules are further linked by C-HO and C-H [pi] interactions, forming a three-dimensional network.

Related literature

For a related structure and the synthesis and applications of carbazole derivatives, see: Archana et al. (2010). For ring conformations, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₈H₁₅NO₂
M_r = 277.31
Triclinic, $[P \overline 1]$
a = 6.3925 (3) Å
b = 7.9880 (4) Å
c = 13.8629 (8) Å
= 83.151 (5)°
= 81.649 (4)°
= 78.921 (4)°
V = 684.28 (6) Å³
Z = 2
Cu K radiation
= 0.70 mm^-1
T = 123 K
0.34 × 0.26 × 0.12 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) T_min = 0.816, T_max = 1.000
4371 measured reflections
2724 independent reflections
2382 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.132
S = 1.05
2724 reflections
199 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.41 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg1 are the centroids of the pyrrole (N9/C9A/C4A/C4B/C8A) and furan (O11/C12-C15)rings, respectively.

D-HA	D-H	HA	DA	D-HA
N9-H9O1ⁱ	0.867 (18)	1.961 (18)	2.8069 (17)	164.9 (17)
C14-H14O1ⁱⁱ	0.95	2.55	3.250 (2)	130
C4-H4BCg2ⁱⁱⁱ	0.99	2.60	3.5176 (16)	154
C17-H17BCg1ⁱⁱⁱ	0.98	2.89	3.807 (2)	156
Symmetry codes: (i) -x+2, -y+1, -z; (ii) x-1, y, z; (iii) -x+1, -y+2, -z.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5183 ).

Acknowledgements

RJB acknowledges the NSF-MRI program (grant No. CHE0619278) for funds to purchase the X-ray diffractometer. SKG wishes to thank the USIEF for the award of a Fulbright-Nehru Senior Fellowship.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Archana, R., Yamuna, E., Rajendra Prasad, K. J., Thiruvalluvar, A. & Butcher, R. J. (2010). Acta Cryst. E66, o3145.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds