[Journal logo]

Volume 69 
Part 9 
Pages o1420-o1421  
September 2013  

Received 1 August 2013
Accepted 8 August 2013
Online 14 August 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.053
wR = 0.172
Data-to-parameter ratio = 12.3
Details
Open access

2-(4-Chloro-2-nitrophenyl)-9-phenylsulfonyl-9H-carbazole-3-carbaldehyde

aDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: ksethusankar@yahoo.co.in

In the title compound, C25H15ClN2O6S, the carbazole ring system is essentially planar, with a maximum deviation of 0.152 (3) Å for the C atom to which the 4-chloro-2-nitrophenyl ring is attached. Its mean plane is almost orthogonal to the phenylsulfonyl and nitrophenyl rings, making dihedral angles of 82.64 (14) and 79.89 (13)°, respectively. The N atom of the nitro group deviates by 0.032 (3) Å from the benzene ring to which it is attached. The molecular structure features intramolecular O-H...O and C-H...O hydrogen bonds, which generate three S(6) ring motifs. In the crystal, molecules are linked by C-H...O hydrogen bonds, which generate C(6) and C(9) chains running in the [100] and [010] directions, respectively, forming a two-dimensional network lying parallel to (001). There are also R43(28) supramolecular graph-set ring motifs enclosed within these networks.

Related literature

For the biological activity and uses of carbazole derivatives, see: Itoigawa et al. (2000[Itoigawa, M., Kashiwada, Y., Ito, C., Furukawa, H., Tachibana, Y., Bastow, K. F. & Lee, K. H. (2000). J. Nat. Prod. 63, 893-897.]); Ramsewak et al. (1999[Ramsewak, R. S., Nair, M. G., Strasburg, G. M., DeWitt, D. L. & Nitiss, J. L. (1999). J. Agric. Food Chem. 47, 444-447.]). For their electronic properties and applications, see: Friend et al. (1999[Friend, R. H., Gymer, R. W., Holmes, A. B., Burroughes, J. H., Mark, R. N., Taliani, C., Bradley, D. D. C., Dos Santos, D. A., Bredas, J. L., Logdlund, M. & Salaneck, W. R. (1999). Nature (London), 397, 121-127.]); Zhang et al. (2004[Zhang, Q., Chen, J., Cheng, Y., Wang, L., Ma, D., Jing, X. & Wang, F. (2004). J. Mater. Chem. 14, 895-900.]). For related structures, see: Chakkaravarthi et al. (2008[Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o1667-o1668.]). For bond-length distortions, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin. Trans. 2, pp. S1-19.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For the Thorpe-Ingold effect, see: Bassindale et al. (1984[Bassindale, A. (1984). The Third Dimension in Organic Chemistry, ch. 1, p. 11. New York: John Wiley and Sons.]).

[Scheme 1]

Experimental

Crystal data
  • C25H15ClN2O6S

  • Mr = 506.91

  • Monoclinic, P 21 /c

  • a = 8.1947 (15) Å

  • b = 14.384 (3) Å

  • c = 18.795 (3) Å

  • [beta] = 90.963 (9)°

  • V = 2215.2 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.31 mm-1

  • T = 296 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.910, Tmax = 0.939

  • 16586 measured reflections

  • 3893 independent reflections

  • 2809 reflections with I > 2[sigma](I)

  • Rint = 0.056

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

  • wR(F2) = 0.172

  • S = 1.05

  • 3893 reflections

  • 316 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2 0.82 1.91 2.629 (4) 146
C2-H2...O3 0.93 2.36 2.949 (5) 121
C9-H9...O4 0.93 2.31 2.910 (4) 122
C13-H13...O4i 0.93 2.56 3.411 (4) 153
C18-H18...O4ii 0.93 2.53 3.287 (4) 139
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (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 Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2632 ).


Acknowledgements

The authors thank Mr T. Srinivasan and Dr D. Velmurugan the Technology Business Incubator (TBI), CAS in Crystallography and Biophysics, University of Madras, Maraimalai Campus, Chennai, and the Department of Science and Technology (DST) for the data collection.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin. Trans. 2, pp. S1-19.
Bassindale, A. (1984). The Third Dimension in Organic Chemistry, ch. 1, p. 11. New York: John Wiley and Sons.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o1667-o1668.  [CSD] [CrossRef] [ChemPort] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Friend, R. H., Gymer, R. W., Holmes, A. B., Burroughes, J. H., Mark, R. N., Taliani, C., Bradley, D. D. C., Dos Santos, D. A., Bredas, J. L., Logdlund, M. & Salaneck, W. R. (1999). Nature (London), 397, 121-127.  [ISI] [CrossRef] [ChemPort]
Itoigawa, M., Kashiwada, Y., Ito, C., Furukawa, H., Tachibana, Y., Bastow, K. F. & Lee, K. H. (2000). J. Nat. Prod. 63, 893-897.  [ISI] [CrossRef] [PubMed] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Ramsewak, R. S., Nair, M. G., Strasburg, G. M., DeWitt, D. L. & Nitiss, J. L. (1999). J. Agric. Food Chem. 47, 444-447.  [ISI] [CrossRef] [PubMed] [ChemPort]
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]
Zhang, Q., Chen, J., Cheng, Y., Wang, L., Ma, D., Jing, X. & Wang, F. (2004). J. Mater. Chem. 14, 895-900.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1420-o1421   [ doi:10.1107/S1600536813022253 ]

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.