(2E)-3-[4-(Benz­yloxy)phen­yl]-1-(2,6-dichloro-3-fluoro­phen­yl)prop-2-en-1-one

Praveen, A.S.; Yathirajan, H.S.; Gerber, T.; Brecht, B. van; Betz, R.

doi:10.1107/S1600536812046855

Volume 68
Part 12
Page o3386
December 2012

Received 4 November 2012
Accepted 14 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.101
Data-to-parameter ratio = 19.3
Details

(2E)-3-[4-(Benzyloxy)phenyl]-1-(2,6-dichloro-3-fluorophenyl)prop-2-en-1-one

Aletti S. Praveen,^a Hemmige S. Yathirajan,^a Thomas Gerber,^b Benjamin van Brecht ^b and Richard Betz ^b ^*

^aUniversity of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India, and ^bNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

In the title compound, C₂₂H₁₅Cl₂FO₂, a chalcone derivative featuring a threefold-halogenated aromatic substituent, the conformation about the C=C bond is E. In the crystal C-HF and C-HCl contacts connect the molecules into undulating sheets parallel to (101). In addition, C-H [pi] interactions are also present.

Related literature

For background to possible applications of chalcones in pharmacy and industry, see: Lin et al. (2002); Modzelewska et al. (2006); Svetaz et al. (2004); Sarojini et al. (2006). For related structures, see: Yathirajan et al. (2006); Betz et al. (2012). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₂₂H₁₅Cl₂FO₂
M_r = 401.24
Monoclinic, P 2₁ /c
a = 9.1977 (2) Å
b = 21.6887 (4) Å
c = 11.6072 (2) Å
= 124.629 (1)°
V = 1905.29 (6) Å³
Z = 4
Mo K radiation
= 0.36 mm^-1
T = 200 K
0.40 × 0.17 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.681, T_max = 0.746
17237 measured reflections
4712 independent reflections
3729 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.101
S = 1.02
4712 reflections
244 parameters
H-atom parameters constrained
_max = 0.40 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C21-C26 ring.

D-HA	D-H	HA	DA	D-HA
C23-H23F1ⁱ	0.95	2.55	3.375 (2)	145
C34-H34Cl1ⁱⁱ	0.95	2.80	3.5462 (18)	136
C14-H14Cgⁱⁱⁱ	0.95	2.51	3.297 (2)	140
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x+1, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2298 ).

Acknowledgements

ASP thanks the UOM for research facilities.

References

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organic compounds