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Volume 64 
Part 6 
Pages o958-o959  
June 2008  

Received 24 April 2008
Accepted 27 April 2008
Online 3 May 2008

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.103
Data-to-parameter ratio = 20.6
Details
Open access

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

Hoong-Kun Fun,a* Suchada Chantrapromma,b+ P. S. Patilc and S. M. Dharmaprakashc

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and cDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India
Correspondence e-mail: hkfun@usm.my

In the title compound, C15H10ClNO3, a substituted chalcone, the 2-chlorophenyl and 4-nitrophenyl rings make a dihedral angle of 26.48 (6)°. The nitro group makes a dihedral angle of 11.64 (7)° with the plane of the benzene ring to which it is bound. Weak intramolecular C-H...O and C-H...Cl interactions involving the enone groups generate S(5) ring motifs, which help to stabilize the planarity of the 3-(2-chlorophenyl)prop-2-en-1-one segment of the molecule. In the crystal structure, adjacent molecules are stacked in a head-to-tail fashion into columns along the a axis by [pi]-[pi] interactions [centroid-centroid distance = 3.6955 (8) Å]. Neighbouring columns are linked by weak C-H...O interactions.

Related literature

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.]). For bond-length data, 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-S19.]). For related structures, see, for example: Fun et al. (2007[Fun, H.-K., Patil, P. S., Dharmaprakash, S. M. & Chantrapromma, S. (2007). Acta Cryst. E63, o561-o562.]); Patil et al. (2006b[Patil, P. S., Teh, J. B.-J., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2006b). Acta Cryst. E62, o896-o898.]; 2007a[Patil, P. S., Chantrapromma, S., Fun, H.-K. & Dharmaprakash, S. M. (2007a). Acta Cryst. E63, o1738-o1740.],b[Patil, P. S., Fun, H.-K., Chantrapromma, S. & Dharmaprakash, S. M. (2007b). Acta Cryst. E63, o2497-o2498.],c[Patil, P. S., Dharmaprakash, S. M., Ramakrishna, K., Fun, H.-K., Sai Santosh Kumar, R. & Rao, D. N. (2007c). J. Cryst. Growth, 303, 520-524.]). For background to the applications of substituted chalcones, see, for example: Agrinskaya et al. (1999[Agrinskaya, N. V., Lukoshkin, V. A., Kudryavtsev, V. V., Nosova, G. I., Solovskaya, N. A. & Yakimanski, A. V. (1999). Phys. Solid State, 41, 1914-1917.]); Gu et al. (2008[Gu, B., Ji, W., Patil, P. S., Dharmaprakash, S. M. & Wang, H. T. (2008). Appl. Phys. Lett. 92, 091118-091121.]); Patil et al. (2006a[Patil, P. S., Dharmaprakash, S. M., Fun, H.-K. & Karthikeyan, M. S. (2006a). J. Cryst. Growth, 297, 111-116.], 2007c[Patil, P. S., Dharmaprakash, S. M., Ramakrishna, K., Fun, H.-K., Sai Santosh Kumar, R. & Rao, D. N. (2007c). J. Cryst. Growth, 303, 520-524.],d[Patil, P. S., Teh, J. B.-J., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2007d). Acta Cryst. E63, o2122-o2123.]).

[Scheme 1]

Experimental

Crystal data

  • C15H10ClNO3

  • Mr = 287.69

  • Monoclinic, C 2/c

  • a = 13.7003 (2) Å

  • b = 7.3659 (1) Å

  • c = 25.9954 (4) Å

  • [beta] = 102.290 (1)°

  • V = 2563.21 (7) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.30 mm-1

  • T = 100.0 (1) K

  • 0.36 × 0.22 × 0.14 mm
Data collection

  • Bruker SMART APEX2 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.899, Tmax = 0.957

  • 27534 measured reflections

  • 3736 independent reflections

  • 3008 reflections with I > 2[sigma](I)

  • Rint = 0.043
Refinement

  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.103

  • S = 1.07

  • 3736 reflections

  • 181 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4...O2i 0.93 2.58 3.4284 (18) 152
C5-H5...O1ii 0.93 2.59 3.2996 (17) 134
C7-H7...Cl1 0.93 2.60 3.0531 (14) 110
C7-H7...O1 0.93 2.47 2.7981 (16) 101
C12-H12...O1iii 0.93 2.56 3.3298 (17) 141
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) x, y-1, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2489 ).

Acknowledgements

PSP thanks the DRDO, Government of India, for a Senior Research Fellowship (SRF). This work is supported by the Department of Science and Technology (DST), Government of India, under grant No. SR/S2/LOP-17/2006. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

Agrinskaya, N. V., Lukoshkin, V. A., Kudryavtsev, V. V., Nosova, G. I., Solovskaya, N. A. & Yakimanski, A. V. (1999). Phys. Solid State, 41, 1914-1917.  [ISI] [CrossRef] [ChemPort]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Fun, H.-K., Patil, P. S., Dharmaprakash, S. M. & Chantrapromma, S. (2007). Acta Cryst. E63, o561-o562.  [CrossRef] [details]
Gu, B., Ji, W., Patil, P. S., Dharmaprakash, S. M. & Wang, H. T. (2008). Appl. Phys. Lett. 92, 091118-091121.  [CrossRef]
Patil, P. S., Chantrapromma, S., Fun, H.-K. & Dharmaprakash, S. M. (2007a). Acta Cryst. E63, o1738-o1740.  [CSD] [CrossRef] [details]
Patil, P. S., Dharmaprakash, S. M., Fun, H.-K. & Karthikeyan, M. S. (2006a). J. Cryst. Growth, 297, 111-116.  [CrossRef] [ChemPort]
Patil, P. S., Dharmaprakash, S. M., Ramakrishna, K., Fun, H.-K., Sai Santosh Kumar, R. & Rao, D. N. (2007c). J. Cryst. Growth, 303, 520-524.  [CrossRef] [ChemPort]
Patil, P. S., Fun, H.-K., Chantrapromma, S. & Dharmaprakash, S. M. (2007b). Acta Cryst. E63, o2497-o2498.  [CrossRef] [details]
Patil, P. S., Teh, J. B.-J., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2006b). Acta Cryst. E62, o896-o898.  [CrossRef] [details]
Patil, P. S., Teh, J. B.-J., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2007d). Acta Cryst. E63, o2122-o2123.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.  [ISI] [CrossRef] [ChemPort] [details]

Acta Cryst (2008). E64, o958-o959   [ doi:10.1107/S160053680801218X ]

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