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Volume 68 
Part 1 
Pages o74-o75  
January 2012  

Received 5 December 2011
Accepted 6 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.055
wR = 0.128
Data-to-parameter ratio = 19.7
Details
Open access

(1E,4E)-1-(3-Nitrophenyl)-5-phenylpenta-1,4-dien-3-one

aDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India,bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA,cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,dDepartment of Chemistry, P. A. College of Engineering, Nadupadav, Mangalore-574 153, India, and eDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
Correspondence e-mail: akkurt@erciyes.edu.tr

In the title compound, C17H13NO3, the dihedral angle between the benzene rings is 31.21 (5)°. In the crystal, inversion dimers linked by pairs of C-H...O hydrogen bonds occur. A C-H...[pi] interaction is also indicated.

Related literature

For the pharmacological importance of chalcones and bis chalcones, see: Sarojini et al. (2006[Sarojini, B. K., Narayana, B., Ashalatha, B. V., Indira, J. & Lobo, K. G. (2006). J. Cryst. Growth, 295, 54-59.]); Dhar (1981[Dhar, D. N. (1981). The Chemistry of Chalcones and Related Compounds. New York: John Wiley.]); Dimmock et al. (1999[Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125-1149.]); Satyanarayana et al. (2004[Satyanarayana, M., Tiwari, P., Tripathi, B. K., Sriwastava, A. K. & Pratap, R. (2004). Bioorg. Med. Chem. 12, 883-887.]). For our work on synthesis of different derivatives of chalcones, see: Baktir et al. (2011[Baktir, Z., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o1292-o1293.]); Fun et al. (2010[Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010). Acta Cryst. E66, o582-o583.]); Jasinski et al. (2010[Jasinski, J. P., Guild, C. J., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010). Acta Cryst. E66, o2018.]); Samshuddin et al. (2011a[Samshuddin, S., Narayana, B., Sarojini, B. K., Khan, M. T. H., Yathirajan, H. S., Raj, C. G. D. & Raghavendra, R. (2011a). Med Chem Res. doi:10.1007/s00044-011-9735-9. ],b[Samshuddin, S., Narayana, B., Shetty, D. N. & Raghavendra, R. (2011b). Der Pharm. Chem. 3, 232-240.],c[Samshuddin, S., Butcher, R. J., Akkurt, M., Narayana, B., Yathirajan, H. S. & Sarojini, B. K. (2011c). Acta Cryst. E67, o1954-o1955.]). For related structures, see: Butcher et al. (2006a[Butcher, R. J., Yathirajan, H. S., Sarojini, B. K., Narayana, B. & Indira, J. (2006a). Acta Cryst. E62, o1910-o1912.],b[Butcher, R. J., Yathirajan, H. S., Sarojini, B. K., Narayana, B. & Vijaya Raj, K. K. (2006b). Acta Cryst. E62, o1973-o1975.]; 2007a[Butcher, R. J., Jasinski, J. P., Yathirajan, H. S., Bindya, S., Narayana, B. & Sarojini, B. K. (2007a). Acta Cryst. E63, o3115.],b[Butcher, R. J., Jasinski, J. P., Sarojini, B. K., Yathirajan, H. S., Bindya, S. & Narayana, B. (2007b). Acta Cryst. E63, o3213-o3214.],c[Butcher, R. J., Jasinski, J. P., Narayana, B., Sarojini, B. K., Bindya, S. & Yathirajan, H. S. (2007c). Acta Cryst. E63, o3270-o3271.]); Harrison et al. (2006[Harrison, W. T. A., Sarojini, B. K., Vijaya Raj, K. K., Yathirajan, H. S. & Narayana, B. (2006). Acta Cryst. E62, o1522-o1523.]); Hu et al. (2004[Hu, X.-R., Gu, J.-M. & Xu, W.-M. (2004). Acta Cryst. E60, o1437-o1438.]); Fischer et al. (2007[Fischer, A., Yathirajan, H. S., Sarojini, B. K., Bindya, S. & Narayana, B. (2007). Acta Cryst. E63, o2832.]); Patil et al. (2007[Patil, P. S., Teh, J. B.-J., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2007). Acta Cryst. E63, o2122-o2123.]); Zhao et al. (2007[Zhao, B., Rong, Y.-Z. & Huang, W. (2007). Acta Cryst. E63, o2971.]).

[Scheme 1]

Experimental

Crystal data
  • C17H13NO3

  • Mr = 279.28

  • Monoclinic, P 21 /c

  • a = 11.9806 (6) Å

  • b = 9.8955 (4) Å

  • c = 12.5562 (7) Å

  • [beta] = 114.992 (7)°

  • V = 1349.21 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.44 × 0.34 × 0.08 mm

Data collection
  • Oxford Diffraction Xcalibur Ruby Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.969, Tmax = 1.000

  • 7835 measured reflections

  • 3746 independent reflections

  • 2453 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.128

  • S = 1.02

  • 3746 reflections

  • 190 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C12-C17 phenyl ring.

D-H...A D-H H...A D...A D-H...A
C2-H2A...O3i 0.93 2.59 3.412 (2) 147
C5-H5A...Cg1ii 0.93 2.62 3.3915 (19) 141
Symmetry codes: (i) -x+1, -y, -z+1; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]), PARST (Nardelli, 1983[Nardelli, M. (1983). Comput. Chem. 7, 95-98.]) 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: TK5031 ).


Acknowledgements

BN thanks the UGC for financial assistance through SAP and BSR one-time grants for the purchase of chemicals. HSY thanks the University of Mysore for research facilities. RJB wishes to acknowledge the NSF-MRI program (grant CHE-0619278) for funds to purchase the diffractometer.

References

Baktir, Z., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o1292-o1293.  [CSD] [CrossRef] [details]
Butcher, R. J., Jasinski, J. P., Narayana, B., Sarojini, B. K., Bindya, S. & Yathirajan, H. S. (2007c). Acta Cryst. E63, o3270-o3271.  [CSD] [CrossRef] [details]
Butcher, R. J., Jasinski, J. P., Sarojini, B. K., Yathirajan, H. S., Bindya, S. & Narayana, B. (2007b). Acta Cryst. E63, o3213-o3214.  [CSD] [CrossRef] [details]
Butcher, R. J., Jasinski, J. P., Yathirajan, H. S., Bindya, S., Narayana, B. & Sarojini, B. K. (2007a). Acta Cryst. E63, o3115.  [CSD] [CrossRef] [details]
Butcher, R. J., Yathirajan, H. S., Sarojini, B. K., Narayana, B. & Indira, J. (2006a). Acta Cryst. E62, o1910-o1912.  [CSD] [CrossRef] [details]
Butcher, R. J., Yathirajan, H. S., Sarojini, B. K., Narayana, B. & Vijaya Raj, K. K. (2006b). Acta Cryst. E62, o1973-o1975.  [CSD] [CrossRef] [details]
Dhar, D. N. (1981). The Chemistry of Chalcones and Related Compounds. New York: John Wiley.
Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125-1149.  [ISI] [PubMed] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Fischer, A., Yathirajan, H. S., Sarojini, B. K., Bindya, S. & Narayana, B. (2007). Acta Cryst. E63, o2832.  [CSD] [CrossRef] [details]
Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010). Acta Cryst. E66, o582-o583.  [CSD] [CrossRef] [details]
Harrison, W. T. A., Sarojini, B. K., Vijaya Raj, K. K., Yathirajan, H. S. & Narayana, B. (2006). Acta Cryst. E62, o1522-o1523.  [CSD] [CrossRef] [details]
Hu, X.-R., Gu, J.-M. & Xu, W.-M. (2004). Acta Cryst. E60, o1437-o1438.  [CSD] [CrossRef] [details]
Jasinski, J. P., Guild, C. J., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010). Acta Cryst. E66, o2018.  [CSD] [CrossRef] [details]
Nardelli, M. (1983). Comput. Chem. 7, 95-98.  [CrossRef] [ChemPort]
Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Patil, P. S., Teh, J. B.-J., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2007). Acta Cryst. E63, o2122-o2123.  [CSD] [CrossRef] [details]
Samshuddin, S., Butcher, R. J., Akkurt, M., Narayana, B., Yathirajan, H. S. & Sarojini, B. K. (2011c). Acta Cryst. E67, o1954-o1955.  [CrossRef] [ChemPort] [details]
Samshuddin, S., Narayana, B., Sarojini, B. K., Khan, M. T. H., Yathirajan, H. S., Raj, C. G. D. & Raghavendra, R. (2011a). Med Chem Res. doi:10.1007/s00044-011-9735-9.
Samshuddin, S., Narayana, B., Shetty, D. N. & Raghavendra, R. (2011b). Der Pharm. Chem. 3, 232-240.  [ChemPort]
Sarojini, B. K., Narayana, B., Ashalatha, B. V., Indira, J. & Lobo, K. G. (2006). J. Cryst. Growth, 295, 54-59.  [ISI] [CrossRef] [ChemPort]
Satyanarayana, M., Tiwari, P., Tripathi, B. K., Sriwastava, A. K. & Pratap, R. (2004). Bioorg. Med. Chem. 12, 883-887.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Zhao, B., Rong, Y.-Z. & Huang, W. (2007). Acta Cryst. E63, o2971.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o74-o75   [ doi:10.1107/S1600536811052548 ]

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