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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 [sigma](C-C) = 0.002 Å
R = 0.047
wR = 0.132
Data-to-parameter ratio = 13.7
Details
Open access

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

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-H...O hydrogen bonds form an R22(10) ring. Molecules are further linked by C-H...O 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[Archana, R., Yamuna, E., Rajendra Prasad, K. J., Thiruvalluvar, A. & Butcher, R. J. (2010). Acta Cryst. E66, o3145.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C18H15NO2

  • Mr = 277.31

  • Triclinic, [P \overline 1]

  • a = 6.3925 (3) Å

  • b = 7.9880 (4) Å

  • c = 13.8629 (8) Å

  • [alpha] = 83.151 (5)°

  • [beta] = 81.649 (4)°

  • [gamma] = 78.921 (4)°

  • V = 684.28 (6) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 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[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.816, Tmax = 1.000

  • 4371 measured reflections

  • 2724 independent reflections

  • 2382 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.41 e Å-3

  • [Delta][rho]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-H...A D-H H...A D...A D-H...A
N9-H9...O1i 0.867 (18) 1.961 (18) 2.8069 (17) 164.9 (17)
C14-H14...O1ii 0.95 2.55 3.250 (2) 130
C4-H4B...Cg2iii 0.99 2.60 3.5176 (16) 154
C17-H17B...Cg1iii 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[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS86 (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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); 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.  [CSD] [CrossRef] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o150  [ doi:10.1107/S1600536812051203 ]

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