(E)-1-(2-Bromo­phen­yl)-3-(2,5-dimeth­oxy­phen­yl)prop-2-en-1-one

Jasinski, J.P.; Butcher, R.J.; Veena, K.; Narayana, B.; Yathirajan, H.S.

doi:10.1107/S1600536810025638

Volume 66
Part 8
Page o1952
August 2010

Received 9 June 2010
Accepted 29 June 2010
Online 7 July 2010

Key indicators
Single-crystal X-ray study
T = 110 K
Mean (C-C) = 0.005 Å
R = 0.053
wR = 0.146
Data-to-parameter ratio = 14.8
Details

(E)-1-(2-Bromophenyl)-3-(2,5-dimethoxyphenyl)prop-2-en-1-one

Jerry P. Jasinski,^a ^* Ray J. Butcher,^b K. Veena,^c B. Narayana ^c and H. S. Yathirajan ^d

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA,^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA,^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
Correspondence e-mail: jjasinski@keene.edu

The title compound, C₁₇H₁₅BrO₃, is a chalcone with the 2-bromophenyl and 2,5-dimethoxyphenyl rings bonded at opposite ends of a propene group. The dihedral angle between the mean planes of the ortho-bromo and ortho,meta-dimethoxy-substituted benzene rings is 77.3 (1)°. The dihedral angles between the mean plane of the prop-2-ene-1-one group and the mean planes of the 2-bromophenyl and 2,5-dimethoxyphenyl rings are 58.6 (1) and 30.7 (4)°, respectively. Weak C-HO, C-HBr and [pi] - [pi] stacking intermolecular interactions [centroid-centroid distance = 3.650 (2) Å] are present in the structure.

Related literature

For the radical quenching properties of included phenol groups, see: Dhar (1981). For their anticancer activity, see Dimmock et al. (1999). For related structures, see: Ng et al. (2006); Rosli et al. (2006). For standard bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₁₇H₁₅BrO₃
M_r = 347.20
Triclinic, $[P \overline 1]$
a = 7.7643 (9) Å
b = 9.7006 (11) Å
c = 10.2722 (10) Å
= 72.901 (10)°
= 78.487 (9)°
= 86.359 (9)°
V = 724.59 (14) Å³
Z = 2
Cu K radiation
= 3.93 mm^-1
T = 110 K
0.54 × 0.26 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.179, T_max = 0.635
4759 measured reflections
2835 independent reflections
2749 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.146
S = 1.05
2835 reflections
192 parameters
H-atom parameters constrained
_max = 2.51 e Å^-3
_min = -1.11 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4-H4Br1ⁱ	0.95	2.95	3.834 (4)	155
C3-H3O2ⁱⁱ	0.95	2.62	3.463 (5)	148
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+2, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2201 ).

Acknowledgements

KV thanks the UGC for the sanction of a Junior Research Fellowship and for an SAP Chemical grant. HSY thanks the UOM for sabbatical leave. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

References

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.
Dhar, D. N. (1981). The Chemistry of Chalcones and Related Compounds. New York: John Wiley.
Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125-1149.
Ng, S.-L., Shettigar, V., Razak, I. A., Fun, H.-K., Patil, P. S. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o1570-o1572.
Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Rosli, M. M., Patil, P. S., Fun, H.-K., Razak, I. A., Dharmaprakash, S. M. & Karthikeyan, M. S. (2006). Acta Cryst. E62, o1460-o1462.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds