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Volume 69 
Part 4 
Pages o558-o559  
April 2013  

Received 18 February 2013
Accepted 12 March 2013
Online 23 March 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.110
Data-to-parameter ratio = 12.8
Details
Open access

The chalcone derivative (E)-1-(4-fluorophenyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one monohydrate

aDepartment of Chemistry, Xavier University of New Orleans, 1 Drexel Drive, Box 114, New Orleans, Louisiana 70125, USA,bDepartment of Chemistry, Xavier University of New Orleans, 1 Drexel Drive, Box 22, New Orleans, Louisiana 70125, USA, and cDepartment of Chemistry, Tulane University, 6400 Freret Street, New Orleans, Louisiana 70118-5698, USA
Correspondence e-mail: flpayton@xula.edu

The title compound, C16H13FO3·H2O, has a cis disposition of the carbonyl and olefin bonds about the enone single bond. The arene rings are inclined to one another by 10.05 (6) Å. In the crystal, molecules are linked via O-H...O hydrogen bonds involving the water molecules, forming loops which are, in turn, linked via O-H.·O and C-H...F hydrogen bonds, forming sheets lying parallel to (103). These networks are linked via [pi]-[pi] interactions [centroid-centroid distance = 3.641 (1) Å] involving inversion-related 4-fluorophenyl and 4-hydroxy-3-methoxyphenyl rings.

Related literature

For background information on the biological activity of chalcones, see: Anto et al. (1995[Anto, R. J., Sukumaran, K., Kuttan, G., Rao, M. N. A., Subbaraju, V. & Kuttan, R. (1995). Cancer Lett. 97, 33-37.]); Calliste et al. (2001[Calliste, C.-A., Le Bail, J.-C., Trouillas, P., Pouget, C., Habrioux, G., Chulia, A.-J. & Duroux, J.-L. (2001). Anticancer Res. 21, 3949-3956.]); Nowakowska (2007[Nowakowska, Z. (2007). Eur. J. Med. Chem. 42, 125-137.]); Kontogiorgis et al. (2008[Kontogiorgis, C., Mantzanidou, M. & Hadjipavlou-Litina, D. (2008). Mini Rev. Med. Chem. 8, 1224-1242.]); Ducki (2009[Ducki, S. (2009). Anti-Cancer Agent Med. Chem. 9, 336-347.]); Batovska & Todorova (2010[Batovska, D. I. & Todorova, I. T. (2010). Curr. Clin. Pharm. 5, 1-29.]); Batovska & Parushev (2010[Batovska, D. I. & Parushev, S. P. (2010). Int. J. Curr. Chem. 1, 217-236.]); Gupta et al. (2010[Gupta, D., Jain, D. K. & Trivedi, P. (2010). Int. J. Chem. Sci. 8, 649-654.]); Varinska et al. (2010[Varinska, L., Ivanova, L. & Mojzis, J. (2010). Int. J. Curr. Chem. 1, 63-71.]); Katsori & Hadjipavlou-Litina (2011[Katsori, A.-M. & Hadjipavlou-Litina, D. (2011). Expert Opin. Ther. Patents, 21, 1575-1596.]); Orlikova, et al. (2011[Orlikova, B., Tasdemir, D., Golais, F., Dicato, M. & Diederich, M. (2011). Genes Nutr. 6, 125-147.]); Yadav et al. (2011[Yadav, V. R., Prasad, S., Sung, B. & Aggarwal, B. B. (2011). Int. Immunopharmacol. 11, 295-309.]); Kathiravan et al. (2012[Kathiravan, M. K., Salake, A. B., Chothe, A. S., Dudhe, P. B., Watode, R. P., Mukta, M. S. & Gadhwe, S. (2012). Bioorgan. Med. Chem. 20, 5678-5698.]); Sahu et al. (2012[Sahu, N. K., Balbhadra, S. S., Choudhary, J. & Kohli, D. V. (2012). Curr. Med. Chem. 19, 209-225.]). For related chalcone structures, see: Rabinovich (1970[Rabinovich, D. (1970). J. Chem. Soc. B, pp. 11-16.]); Ohkura et al. (1973[Ohkura, K., Kashino, S. & Haisa, M. (1973). Bull. Chem. Soc. Jpn, 46, 627-628.]); Hunter & Sanders (1990[Hunter, C. A. & Sanders, J. K. M. (1990). J. Am. Chem. Soc. 112, 5525-5534.]); Arai et al. (1994[Arai, H., Higashigaki, Y., Gotoh, M. & Yano, S. (1994). Jpn J. Appl. Phys. 33, 5755-5758.]); Wu et al. (2006[Wu, M.-H., Yang, X.-H., Zou, W. D., Liu, W.-J. & Li, C. (2006). Z. Kristallogr. New Cryst. Struct. 221, 323-324.]); Teh et al. (2006[Teh, J. B.-J., Patil, P. S., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o2991-o2992.]); Yathirajan et al. (2006[Yathirajan, H. S., Sarojini, B. K., Narayana, B., Bindya, S. & Bolte, M. (2006). Acta Cryst. E62, o3631-o3632.], 2007[Yathirajan, H. S., Mayekar, A. N., Narayana, B., Sarojini, B. K. & Bolte, M. (2007). Acta Cryst. E63, o2200-o2201.]); Butcher et al. (2007[Butcher, R. J., Jasinski, J. P., Mayekar, A. N., Narayana, B. & Yathirajan, H. S. (2007). Acta Cryst. E63, o4059-o4060.]); Hayashi et al. (2009[Hayashi, N., Higuchi, H. & Ninomiya, K. (2009). X/ Interactions in Aromatic Heterocycles: Basic Principles and Recent Advances, Topics in Heterocyclic Chemistry: Heterocyclic Supramolecules II 18, edited by K. Matsumoto & N. Hayashi, pp. 1-35. Heidelberg, Germany: Springer.]).

[Scheme 1]

Experimental

Crystal data
  • C16H13FO3·H2O

  • Mr = 290.29

  • Monoclinic, P 21 /n

  • a = 9.787 (2) Å

  • b = 10.993 (3) Å

  • c = 12.781 (3) Å

  • [beta] = 95.722 (4)°

  • V = 1368.2 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 100 K

  • 0.34 × 0.27 × 0.21 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2009[Sheldrick, G. M. (2009). SADABS. University of Göttingen, Germany.]) Tmin = 0.845, Tmax = 0.978

  • 11909 measured reflections

  • 3203 independent reflections

  • 2855 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.110

  • S = 1.02

  • 3203 reflections

  • 250 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O4i 0.91 (2) 1.74 (2) 2.6479 (14) 173.5 (18)
O4-H4A...O1 0.88 (2) 1.90 (2) 2.7672 (15) 173 (2)
O4-H4B...O2ii 0.83 (3) 2.17 (3) 2.8485 (15) 139 (2)
O4-H4B...O3ii 0.83 (3) 2.38 (3) 3.1283 (15) 151 (2)
C8-H8...F1iii 0.94 (2) 2.48 (2) 3.3931 (17) 164 (1)
Symmetry codes: (i) -x+2, -y, -z+1; (ii) x, y-1, z; (iii) [-x+{\script{7\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2468 ).


Acknowledgements

This work was funded in part by the Louisiana Cancer Research Consortium (LCRC) and the National Center for Research Resources RCMI Program Grant No. 1 G12RR026260-01 (FP-S). The Louisiana Board of Regents is thanked for enhancement grant LEQSF-(2002-03)-ENH-TR-67 with which the Tulane X-ray diffractometer was purchased, and Tulane University is acknowledged for its ongoing support with operational costs for the diffraction facility. Support from the National Science Foundation (grant CHE-0845829 to JPD) is gratefully acknowledged.

References

Anto, R. J., Sukumaran, K., Kuttan, G., Rao, M. N. A., Subbaraju, V. & Kuttan, R. (1995). Cancer Lett. 97, 33-37.  [CrossRef] [ChemPort] [PubMed] [ISI]
Arai, H., Higashigaki, Y., Gotoh, M. & Yano, S. (1994). Jpn J. Appl. Phys. 33, 5755-5758.  [CrossRef] [ChemPort]
Batovska, D. I. & Parushev, S. P. (2010). Int. J. Curr. Chem. 1, 217-236.  [ChemPort]
Batovska, D. I. & Todorova, I. T. (2010). Curr. Clin. Pharm. 5, 1-29.  [CrossRef] [ChemPort]
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Butcher, R. J., Jasinski, J. P., Mayekar, A. N., Narayana, B. & Yathirajan, H. S. (2007). Acta Cryst. E63, o4059-o4060.  [CSD] [CrossRef] [details]
Calliste, C.-A., Le Bail, J.-C., Trouillas, P., Pouget, C., Habrioux, G., Chulia, A.-J. & Duroux, J.-L. (2001). Anticancer Res. 21, 3949-3956.  [PubMed] [ChemPort]
Ducki, S. (2009). Anti-Cancer Agent Med. Chem. 9, 336-347.  [CrossRef] [ChemPort]
Gupta, D., Jain, D. K. & Trivedi, P. (2010). Int. J. Chem. Sci. 8, 649-654.  [ChemPort]
Hayashi, N., Higuchi, H. & Ninomiya, K. (2009). X/[pi] Interactions in Aromatic Heterocycles: Basic Principles and Recent Advances, Topics in Heterocyclic Chemistry: Heterocyclic Supramolecules II 18, edited by K. Matsumoto & N. Hayashi, pp. 1-35. Heidelberg, Germany: Springer.
Hunter, C. A. & Sanders, J. K. M. (1990). J. Am. Chem. Soc. 112, 5525-5534.  [CrossRef] [ChemPort] [ISI]
Kathiravan, M. K., Salake, A. B., Chothe, A. S., Dudhe, P. B., Watode, R. P., Mukta, M. S. & Gadhwe, S. (2012). Bioorgan. Med. Chem. 20, 5678-5698.  [CrossRef] [ChemPort]
Katsori, A.-M. & Hadjipavlou-Litina, D. (2011). Expert Opin. Ther. Patents, 21, 1575-1596.
Kontogiorgis, C., Mantzanidou, M. & Hadjipavlou-Litina, D. (2008). Mini Rev. Med. Chem. 8, 1224-1242.  [CrossRef] [PubMed] [ChemPort]
Nowakowska, Z. (2007). Eur. J. Med. Chem. 42, 125-137.  [ISI] [CrossRef] [PubMed] [ChemPort]
Ohkura, K., Kashino, S. & Haisa, M. (1973). Bull. Chem. Soc. Jpn, 46, 627-628.  [CrossRef] [ChemPort] [ISI]
Orlikova, B., Tasdemir, D., Golais, F., Dicato, M. & Diederich, M. (2011). Genes Nutr. 6, 125-147.  [CrossRef] [ChemPort] [PubMed]
Rabinovich, D. (1970). J. Chem. Soc. B, pp. 11-16.
Sahu, N. K., Balbhadra, S. S., Choudhary, J. & Kohli, D. V. (2012). Curr. Med. Chem. 19, 209-225.  [ISI] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sheldrick, G. M. (2009). SADABS. University of Göttingen, Germany.
Teh, J. B.-J., Patil, P. S., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o2991-o2992.  [CrossRef] [details]
Varinska, L., Ivanova, L. & Mojzis, J. (2010). Int. J. Curr. Chem. 1, 63-71.  [ChemPort]
Wu, M.-H., Yang, X.-H., Zou, W. D., Liu, W.-J. & Li, C. (2006). Z. Kristallogr. New Cryst. Struct. 221, 323-324.  [ChemPort]
Yadav, V. R., Prasad, S., Sung, B. & Aggarwal, B. B. (2011). Int. Immunopharmacol. 11, 295-309.  [ISI] [CrossRef] [ChemPort] [PubMed]
Yathirajan, H. S., Mayekar, A. N., Narayana, B., Sarojini, B. K. & Bolte, M. (2007). Acta Cryst. E63, o2200-o2201.  [CrossRef] [details]
Yathirajan, H. S., Sarojini, B. K., Narayana, B., Bindya, S. & Bolte, M. (2006). Acta Cryst. E62, o3631-o3632.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o558-o559   [ doi:10.1107/S160053681300696X ]

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