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Volume 69 
Part 5 
Pages o790-o791  
May 2013  

Received 13 April 2013
Accepted 21 April 2013
Online 27 April 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.005 Å
R = 0.048
wR = 0.100
Data-to-parameter ratio = 13.9
Details
Open access

(2E)-1-(4-Chlorophenyl)-3-(4-nitrophenyl)prop-2-en-1-one

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA,cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and dDepartment of Chemistry, P.A. College of Engineering, Nadupadavu, Mangalore 574 153, India
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C15H10ClNO3, a substituted chalcone, the dihedral angle between the benzene rings is 5.1 (7)°. The nitro group makes a dihedral angle of 12.5 (3)° with the benzene ring to which it is attached. In the crystal, weak C-H...O interactions link the molecules into a one-dimensional array along [010]. The crystal studied was an inversion twin, with a refined ratio for the twin components of 0.6060 (9):0.3939 (1).

Related literature

For the biochemical activity of chalcones, see: Dimmock et al. (1999[Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125-1149.]). For different chalcone derivatives, see: Samshuddin et al. (2010[Samshuddin, S., Narayana, B., Yathirajan, H. S., Safwan, A. P. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1279-o1280.]); Fun et al. (2010a[Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010a). Acta Cryst. E66, o582-o583.],b[Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010b). Acta Cryst. E66, o864-o865.]); Jasinski et al. (2010a[Jasinski, J. P., Guild, C. J., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010a). Acta Cryst. E66, o1948-o1949.],b[Jasinski, J. P., Guild, C. J., Narayana, B., Nayak, P. S. & Yathirajan, H. S. (2010b). Acta Cryst. E66, o1996.]); Baktir et al. (2011a[Baktir, Z., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011a). Acta Cryst. E67, o1262-o1263.],b[Baktir, Z., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011b). Acta Cryst. E67, o1292-o1293.]). For related structures, see: Jing (2009[Jing, L.-H. (2009). Acta Cryst. E65, o2510.]); Jasinski et al. (2008[Jasinski, J. P., Butcher, R. J., Narayana, B., Lakshmana, K. & Yathirajan, H. S. (2008). Acta Cryst. E64, o1-o2.], 2010a[Jasinski, J. P., Guild, C. J., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010a). Acta Cryst. E66, o1948-o1949.],b[Jasinski, J. P., Guild, C. J., Narayana, B., Nayak, P. S. & Yathirajan, H. S. (2010b). Acta Cryst. E66, o1996.]); Fun et al. (2011[Fun, H.-K., Chia, T. S., Narayana, B., Nayak, P. S. & Sarojini, B. K. (2011). Acta Cryst. E67, o3058-o3059.]); Sarojini et al. (2007[Sarojini, B. K., Yathirajan, H. S., Lakshmana, K., Narayana, B. & Bolte, M. (2007). Acta Cryst. E63, o3211.]); Ma (2007[Ma, J.-L. (2007). Acta Cryst. E63, o808-o809.]).

[Scheme 1]

Experimental

Crystal data
  • C15H10ClNO3

  • Mr = 287.69

  • Orthorhombic, P n a 21

  • a = 42.9266 (17) Å

  • b = 5.9741 (3) Å

  • c = 5.0680 (2) Å

  • V = 1299.68 (10) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 2.67 mm-1

  • T = 173 K

  • 0.42 × 0.08 × 0.04 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.803, Tmax = 1.000

  • 12814 measured reflections

  • 2538 independent reflections

  • 2481 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.100

  • S = 1.14

  • 2538 reflections

  • 182 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C12-H12...O2i 0.93 2.69 3.304 (4) 125
C14-H14...O1ii 0.93 2.53 3.219 (4) 131
Symmetry codes: (i) [-x+1, -y-1, z+{\script{1\over 2}}]; (ii) x, y+1, z-1.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. 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: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2627 ).


Acknowledgements

TSY thanks the University of Mysore for research facilities. BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Baktir, Z., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011a). Acta Cryst. E67, o1262-o1263.  [CSD] [CrossRef] [details]
Baktir, Z., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011b). Acta Cryst. E67, o1292-o1293.  [CSD] [CrossRef] [details]
Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125-1149.  [ISI] [PubMed] [ChemPort]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Fun, H.-K., Chia, T. S., Narayana, B., Nayak, P. S. & Sarojini, B. K. (2011). Acta Cryst. E67, o3058-o3059.  [CSD] [CrossRef] [ChemPort] [details]
Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010a). Acta Cryst. E66, o582-o583.  [CSD] [CrossRef] [ChemPort] [details]
Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010b). Acta Cryst. E66, o864-o865.  [CrossRef] [ChemPort] [details]
Jasinski, J. P., Butcher, R. J., Narayana, B., Lakshmana, K. & Yathirajan, H. S. (2008). Acta Cryst. E64, o1-o2.  [CSD] [CrossRef] [ChemPort] [details]
Jasinski, J. P., Guild, C. J., Narayana, B., Nayak, P. S. & Yathirajan, H. S. (2010b). Acta Cryst. E66, o1996.  [CSD] [CrossRef] [details]
Jasinski, J. P., Guild, C. J., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010a). Acta Cryst. E66, o1948-o1949.  [CSD] [CrossRef] [ChemPort] [details]
Jing, L.-H. (2009). Acta Cryst. E65, o2510.  [CSD] [CrossRef] [details]
Ma, J.-L. (2007). Acta Cryst. E63, o808-o809.  [CSD] [CrossRef] [ChemPort] [details]
Samshuddin, S., Narayana, B., Yathirajan, H. S., Safwan, A. P. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1279-o1280.  [CSD] [CrossRef] [ChemPort] [details]
Sarojini, B. K., Yathirajan, H. S., Lakshmana, K., Narayana, B. & Bolte, M. (2007). Acta Cryst. E63, o3211.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o790-o791   [ doi:10.1107/S1600536813010854 ]

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