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Volume 69 
Part 10 
Pages o1508-o1509  
October 2013  

Received 29 August 2013
Accepted 1 September 2013
Online 7 September 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.146
Data-to-parameter ratio = 17.0
Details
Open access

1,5-Bis(4-chlorophenyl)-3-(4-methylphenyl)pentane-1,5-dione

aPostgraduate Research Department of Chemistry, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India,bPostgraduate Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India,cDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, 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, C24H20Cl2O2, the central methylbenzene ring forms dihedral angles of 42.47 (10) and 34.34 (10)° with the terminal 4-chlorophenyl fragments. The dihedral angle between the chlorobenzene rings is 34.45 (11)°. A weak intramolecular C-H...O interaction generates an S(6) ring motif. The crystal packing exhibits weak C-H...O hydrogen bonds and C-H...[pi] interactions.

Related literature

For the synthesis of 1,5-diketones, see: Yang et al. (2005[Yang, J.-X., Tao, X.-T., Yuan, C. X., Yan, Y. X., Wang, L., Liu, Z., Ren, Y. & Jiang, M. H. (2005). J. Am. Chem. Soc. 127, 3278-3279.]); Hirsch & Bailey (1978[Hirsch, S. S. & Bailey, W. J. (1978). J. Org. Chem. 43, 4090-4094.]). For the crystal structures of related compounds, see: Qiu et al. (2006[Qiu, X.-Y., Ma, J.-L. & Liu, W.-S. (2006). Acta Cryst. E62, o4565-o4566.]); Insuasty et al. (2006[Insuasty, B., Torres, H., Cobo, J., Low, J. N. & Glidewell, C. (2006). Acta Cryst. C62, o39-o41.]); Jasinski et al. (2007[Jasinski, J. P., Butcher, R. J., Yathirajan, H. S., Narayana, B. & Swamy, M. T. (2007). Acta Cryst. E63, o4808-o4809.]); Huang et al. (2008[Huang, X., Xin, F., Shi, Q.-L., Wang, Y. & Wei, G.-D. (2008). Acta Cryst. E64, o2454.]); Lei & Bai (2009[Lei, X. & Bai, X. (2009). Acta Cryst. E65, o514.]); Dutkiewicz et al. (2010[Dutkiewicz, G., Chidan Kumar, C. S., Yathirajan, H. S., Narayana, B. & Kubicki, M. (2010). Acta Cryst. E66, o816.]); Fun et al. (2011[Fun, H.-K., Suwunwong, T., Boonnak, N. & Chantrapromma, S. (2011). Acta Cryst. E67, o3416-o3417.]). For the applications of delocalized [pi]-systems, see: Burroughes et al. (1990[Burroughes, J. H., Bradley, D. D. C., Brown, A. R., Marks, R. N., Mackay, K., Friend, R. H., Burns, P. L. & Holmes, A. B. (1990). Nature (London), 347, 539-541.]); Smith et al. (2005[Smith, C. B., Raston, C. L. & Sobolev, A. N. (2005). Green Chem. 7, 650-654.]); Li et al. (2004[Li, Y. N., Ding, J. F., Day, M., Tao, Y., Lu, J. P. & D'iorio, M. (2004). Chem. Mater. 16, 2165-2173.]); Sariciftci et al. (1992[Sariciftci, N. S., Smilowitz, L. & Heeger, A. J. (1992). Science, 258, 1474-1476.]). 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. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C24H20Cl2O2

  • Mr = 411.30

  • Monoclinic, P 21 /c

  • a = 18.6794 (11) Å

  • b = 7.5477 (4) Å

  • c = 15.5196 (8) Å

  • [beta] = 103.622 (5)°

  • V = 2126.5 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.32 mm-1

  • T = 296 K

  • 0.51 × 0.42 × 0.37 mm

Data collection
  • Agilent Xcalibur Ruby Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.443, Tmax = 1.000

  • 14252 measured reflections

  • 4341 independent reflections

  • 3735 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.146

  • S = 1.07

  • 4341 reflections

  • 255 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C31-C36 methylbenzene ring.

D-H...A D-H H...A D...A D-H...A
C4-H4A...O1 0.97 2.56 3.130 (3) 118
C16-H16...O5i 0.93 2.44 3.270 (3) 149
C55-H55...Cg2ii 0.93 2.97 3.629 (2) 129
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) x, y+1, z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: DIRDIF2008 (Beurskens et al., 2008[Beurskens, P. T., Beurskens, G., de Gelder, R., Smits, J. M. M., García-Granda, S. & Gould, R. O. (2008). DIRDIF2008. Crystallography Laboratory, Radboud University Nijmegen, The Netherlands.]); 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: JJ2174 ).


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, Oxfordshire, England.
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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Beurskens, P. T., Beurskens, G., de Gelder, R., Smits, J. M. M., García-Granda, S. & Gould, R. O. (2008). DIRDIF2008. Crystallography Laboratory, Radboud University Nijmegen, The Netherlands.
Burroughes, J. H., Bradley, D. D. C., Brown, A. R., Marks, R. N., Mackay, K., Friend, R. H., Burns, P. L. & Holmes, A. B. (1990). Nature (London), 347, 539-541.  [CrossRef] [ChemPort] [Web of Science]
Dutkiewicz, G., Chidan Kumar, C. S., Yathirajan, H. S., Narayana, B. & Kubicki, M. (2010). Acta Cryst. E66, o816.  [CrossRef] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Fun, H.-K., Suwunwong, T., Boonnak, N. & Chantrapromma, S. (2011). Acta Cryst. E67, o3416-o3417.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Hirsch, S. S. & Bailey, W. J. (1978). J. Org. Chem. 43, 4090-4094.  [CrossRef] [ChemPort]
Huang, X., Xin, F., Shi, Q.-L., Wang, Y. & Wei, G.-D. (2008). Acta Cryst. E64, o2454.  [CSD] [CrossRef] [IUCr Journals]
Insuasty, B., Torres, H., Cobo, J., Low, J. N. & Glidewell, C. (2006). Acta Cryst. C62, o39-o41.  [CSD] [CrossRef] [IUCr Journals]
Jasinski, J. P., Butcher, R. J., Yathirajan, H. S., Narayana, B. & Swamy, M. T. (2007). Acta Cryst. E63, o4808-o4809.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Lei, X. & Bai, X. (2009). Acta Cryst. E65, o514.  [CSD] [CrossRef] [IUCr Journals]
Li, Y. N., Ding, J. F., Day, M., Tao, Y., Lu, J. P. & D'iorio, M. (2004). Chem. Mater. 16, 2165-2173.  [Web of Science] [CrossRef] [ChemPort]
Qiu, X.-Y., Ma, J.-L. & Liu, W.-S. (2006). Acta Cryst. E62, o4565-o4566.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sariciftci, N. S., Smilowitz, L. & Heeger, A. J. (1992). Science, 258, 1474-1476.  [CrossRef] [PubMed] [ChemPort] [Web of Science]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Smith, C. B., Raston, C. L. & Sobolev, A. N. (2005). Green Chem. 7, 650-654.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Yang, J.-X., Tao, X.-T., Yuan, C. X., Yan, Y. X., Wang, L., Liu, Z., Ren, Y. & Jiang, M. H. (2005). J. Am. Chem. Soc. 127, 3278-3279.  [Web of Science] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1508-o1509   [ doi:10.1107/S1600536813024355 ]

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