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Volume 69 
Part 5 
Page o638  
May 2013  

Received 25 March 2013
Accepted 25 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.053
wR = 0.139
Data-to-parameter ratio = 16.8
Details
Open access

(2E)-3-(4-Fluorophenyl)-1-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]prop-2-en-1-one1

aApplied Organic Chemistry Department, National Research Centre, Dokki, 12622 Giza, Egypt,bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: edward.tiekink@gmail.com

With respect to the triazole ring in the title compound, C19H16FN3O, the p-tolyl ring is inclined [dihedral angle = 51.79 (11)°], whereas the chalcone residue is almost coplanar [O-C-C-N and C-C-C-C torsion angles = -178.71 (19) and 178.42 (18)°, respectively]. The conformation about the C=C bond [1.328 (3) Å] is E, and the triazole methyl group and the carbonyl O atom are syn. In the crystal, centrosymmetrically related molecules are connected by [pi]-[pi] interactions between the triazole and p-tolyl rings [centroid-centroid distance = 3.6599 (12) Å] and these are linked into a three-dimensional architecture by C-H...N and C-H...[pi] interactions.

Related literature

For the biological activities of chalcone derivatives, see: Abdel-Wahab et al. (2012[Abdel-Wahab, B. F., Abdel-Latif, E., Mohamed, H. A. & Awad, G. E. A. (2012). Eur. J. Med. Chem. 52, 263-268.]); Singh et al. (2012[Singh, P., Raj, R., Kumar, V., Mahajan, M. P., Bedi, P. M., Kaur, T. & Saxena, A. K. (2012). Eur. J. Med. Chem. 47, 594-600.]). For a related structure, see: Abdel-Wahab et al. (2013[Abdel-Wahab, B. F., Abdel-Latif, E., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o639-o640.]).

[Scheme 1]

Experimental

Crystal data
  • C19H16FN3O

  • Mr = 321.35

  • Triclinic, [P \overline 1]

  • a = 6.2890 (5) Å

  • b = 10.8874 (8) Å

  • c = 11.9691 (9) Å

  • [alpha] = 101.144 (7)°

  • [beta] = 92.634 (6)°

  • [gamma] = 91.634 (6)°

  • V = 802.65 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 295 K

  • 0.35 × 0.35 × 0.35 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.887, Tmax = 1.000

  • 6854 measured reflections

  • 3697 independent reflections

  • 2308 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.139

  • S = 1.03

  • 3697 reflections

  • 220 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13-C18 benzene

D-H...A D-H H...A D...A D-H...A
C12-H12C...N3i 0.96 2.49 3.399 (3) 158
C2-H2...Cg1ii 0.93 2.91 3.650 (2) 138
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, 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: SHELXL97 (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 DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7061 ).


Acknowledgements

We thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/03).

References

Abdel-Wahab, B. F., Abdel-Latif, E., Mohamed, H. A. & Awad, G. E. A. (2012). Eur. J. Med. Chem. 52, 263-268.  [ISI] [ChemPort] [PubMed]
Abdel-Wahab, B. F., Abdel-Latif, E., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o639-o640.  [CrossRef] [details]
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Singh, P., Raj, R., Kumar, V., Mahajan, M. P., Bedi, P. M., Kaur, T. & Saxena, A. K. (2012). Eur. J. Med. Chem. 47, 594-600.  [ISI] [CrossRef] [ChemPort] [PubMed]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o638  [ doi:10.1107/S1600536813008246 ]

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