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Volume 69 
Part 11 
Pages o1694-o1695  
November 2013  

Received 11 September 2013
Accepted 12 October 2013
Online 23 October 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.131
Data-to-parameter ratio = 14.7
Details
Open access

Second monoclinic form of (E)-3-(4-fluoro­phen­yl)-1-phenyl­prop-2-en-1-one

aDivisión Académica de Ciencias Básicas, Universidad Juárez Autónoma de Tabasco, AP 24, 86690 Cunduacán, Tab., Mexico, and bCentro de Química, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, 72570 Puebla, Pue., Mexico
Correspondence e-mail: angel.mendoza@correo.buap.mx

The unit-cell dimensions and space group of the second monoclinic polymorph of the title compound, C15H11FO, differ from those of the previously reported form [Jing (2009[Jing, L.-H. (2009). Acta Cryst. E65, o2515.]). Acta Cryst. E65, o2515]. The title compound shows an E conformation of the C=C bond with the 4-fluoro­phenyl group opposite to the benzoyl group. The torsion angle of between the planes of the 4-fluoro­phenyl and benzoyl groups is 10.53 (6)°. In the crystal, weak C-H...O and C-H...F inter­actions form a cross-linked packing motif, building sheets parallel to (-102).

Related literature

For the first monoclinic polymorph of the title compound, see: Jing (2009[Jing, L.-H. (2009). Acta Cryst. E65, o2515.]). For related crystal structures, see: Li et al. (1992[Li, Z., Pa, F. & Su, G. (1992). Acta Cryst. C48, 712-714.]); Li & Su (1994[Li, Z. & Su, G. (1994). Acta Cryst. C50, 126-127.]); For biological properties reports of chalcones, see: Foresti et al. (2005[Foresti, R., Hoque, M., Monti, D., Green, C. J. & Motterlini, R. J. (2005). J. Pharmacol. Exp. Ther. 312, 686-693.]); Nowakowska (2007[Nowakowska, Z. (2007). Eur. J. Med. Chem. 42, 125-137.]); Kouskoura et al. (2008[Kouskoura, M., Hadjipavlou-Litina, D. & Giakoumakou, M. (2008). Med. Chem. 4, 586-596.]); Zhang et al. (2010[Zhang, X.-W., Zhao, D.-H., Quan, Y.-C., Sun, L.-P., Yin, X.-M. & Guan, L.-P. (2010). Med. Chem. Res. 19, 403-412.]); Doan & Tran (2011[Doan, T. N. & Tran, D. T. (2011). Pharmacol. Pharmacy, 2, 282-288.]). For solvent-free synthesis of chalcones, see: Srivastava (2008[Srivastava, Y. K. (2008). Rasayan J. Chem. 1, 884-886.]); Krishnakumar & Swaminathan (2011[Krishnakumar, B. & Swaminathan, M. (2011). J. Mol. Catal. A Chem. 350, 16-25.]); Thirunarayanan et al. (2012[Thirunarayanan, G., Mayavel, P. & Thirumurthy, K. (2012). Spectrochim. Acta Part A, 91, 18-22.]). For applications of chalcones in organic synthesis, see: Prakash et al. (2009[Prakash, O., Kumar, R. & Sehrawat, R. (2009). Eur. J. Med. Chem. 44, 1763-1767.]); Bandgar et al. (2009[Bandgar, B. P., Gawande, S. S., Bodade, R. G., Gawande, N. M. & Khobragade, C. N. (2009). Bioorg. Med. Chem. 17, 8168-8173.]).

[Scheme 1]

Experimental

Crystal data
  • C15H11FO

  • Mr = 226.24

  • Monoclinic, P 21 /c

  • a = 8.6925 (4) Å

  • b = 5.9266 (2) Å

  • c = 22.6456 (9) Å

  • [beta] = 95.423 (4)°

  • V = 1161.41 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.59 × 0.15 × 0.07 mm

Data collection
  • Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer

  • Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.993, Tmax = 0.999

  • 22101 measured reflections

  • 2276 independent reflections

  • 1471 reflections with I > 2[sigma](I)

  • Rint = 0.044

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.131

  • S = 1.01

  • 2276 reflections

  • 155 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.11 e Å-3

  • [Delta][rho]min = -0.11 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5...O1i 0.93 2.49 3.244 (2) 138
C13-H13...F1ii 0.93 2.68 3.465 (2) 142
Symmetry codes: (i) -x+1, -y, -z; (ii) [x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2484 ).


Acknowledgements

The authors wish to acknowledge CONACyT-Gobierno del Estado Tabasco and the Universidad Juárez Autónoma de Tabasco for financial support via projects TAB-2009-C18-122141 and UJAT-2011-C07-22, respectively.

References

Bandgar, B. P., Gawande, S. S., Bodade, R. G., Gawande, N. M. & Khobragade, C. N. (2009). Bioorg. Med. Chem. 17, 8168-8173.  [CrossRef] [PubMed] [ChemPort]
Doan, T. N. & Tran, D. T. (2011). Pharmacol. Pharmacy, 2, 282-288.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Foresti, R., Hoque, M., Monti, D., Green, C. J. & Motterlini, R. J. (2005). J. Pharmacol. Exp. Ther. 312, 686-693.  [CrossRef] [PubMed] [ChemPort]
Jing, L.-H. (2009). Acta Cryst. E65, o2515.  [CSD] [CrossRef] [IUCr Journals]
Kouskoura, M., Hadjipavlou-Litina, D. & Giakoumakou, M. (2008). Med. Chem. 4, 586-596.  [PubMed]
Krishnakumar, B. & Swaminathan, M. (2011). J. Mol. Catal. A Chem. 350, 16-25.  [Web of Science] [CrossRef] [ChemPort]
Li, Z., Pa, F. & Su, G. (1992). Acta Cryst. C48, 712-714.  [CSD] [CrossRef] [IUCr Journals]
Li, Z. & Su, G. (1994). Acta Cryst. C50, 126-127.  [CSD] [CrossRef] [IUCr Journals]
Nowakowska, Z. (2007). Eur. J. Med. Chem. 42, 125-137.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Prakash, O., Kumar, R. & Sehrawat, R. (2009). Eur. J. Med. Chem. 44, 1763-1767.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Srivastava, Y. K. (2008). Rasayan J. Chem. 1, 884-886.  [ChemPort]
Thirunarayanan, G., Mayavel, P. & Thirumurthy, K. (2012). Spectrochim. Acta Part A, 91, 18-22.  [ChemPort]
Zhang, X.-W., Zhao, D.-H., Quan, Y.-C., Sun, L.-P., Yin, X.-M. & Guan, L.-P. (2010). Med. Chem. Res. 19, 403-412.  [Web of Science] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1694-o1695   [ doi:10.1107/S1600536813028079 ]

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