[Journal logo]

Volume 69 
Part 6 
Page o831  
June 2013  

Received 27 April 2013
Accepted 30 April 2013
Online 4 May 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.001 Å
R = 0.053
wR = 0.154
Data-to-parameter ratio = 34.1
Details
Open access

10-Methyl-2-oxo-4-phenyl-2,11-dihydropyrano[2,3-a]carbazole-3-carbonitrile

aPostgraduate Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India,bDepartment of Chemistry, Tamkang University, Tamsui 25137, Taiwan,cDepartment of Chemistry, Bharathiar University, Coimbatore 641 046, Tamilnadu, India, and dDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
Correspondence e-mail: thiruvalluvar.a@gmail.com

In the title molecule, C23H14N2O2, the atoms in the carbazole unit deviate from planarity [maximum deviation from mean plane = 0.1018 (8) Å]. The pyrrole ring makes dihedral angles of 4.44 (5), 3.84 (5), 2.18 (5) and 56.44 (5)° with the pyran, fused benzene rings and phenyl ring, respectively. In the crystal, pairs of N-H...O hydrogen bonds generate R22(14) loops and a C-H...N interaction is also found. Molecules are further linked by a number of [pi]-[pi] interactions [centroid-centroid distances vary from 3.5702 (5) to 3.7068 (6) Å], forming a three-dimensional network.

Related literature

For a related structure, see: Sridharan et al. (2009[Sridharan, M., Rajendra Prasad, K. J., Thomas Gunaseelan, A., Thiruvalluvar, A. & Butcher, R. J. (2009). Acta Cryst. E65, o830.]). 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
  • C23H14N2O2

  • Mr = 350.36

  • Monoclinic, P 21 /n

  • a = 7.8659 (1) Å

  • b = 8.5151 (1) Å

  • c = 25.1137 (4) Å

  • [beta] = 98.133 (2)°

  • V = 1665.17 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 123 K

  • 0.46 × 0.41 × 0.29 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 = 0.978, Tmax = 1.000

  • 27185 measured reflections

  • 8485 independent reflections

  • 7184 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.154

  • S = 1.16

  • 8485 reflections

  • 249 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.64 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N11-H11...O2i 0.874 (18) 2.095 (19) 2.9561 (11) 168.2 (15)
C43-H43...N31ii 0.95 2.56 3.3130 (17) 136
Symmetry codes: (i) -x+2, -y+1, -z; (ii) [-x+{\script{7\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

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: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (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: SHELXL2013 and PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5318 ).


Acknowledgements

RJB acknowledges the NSF-MRI program (grant No. CHE0619278) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [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] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Sridharan, M., Rajendra Prasad, K. J., Thomas Gunaseelan, A., Thiruvalluvar, A. & Butcher, R. J. (2009). Acta Cryst. E65, o830.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o831  [ doi:10.1107/S1600536813011823 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.