(2E)-3-(4-Bromo­phen­yl)-1-(3-chloro­phen­yl)prop-2-en-1-one

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

doi:10.1107/S1600536809053446

Volume 66
Part 1
Page o158
January 2010

Received 5 December 2009
Accepted 11 December 2009
Online 16 December 2009

Key indicators
Single-crystal X-ray study
T = 110 K
Mean (C-C) = 0.005 Å
R = 0.058
wR = 0.164
Data-to-parameter ratio = 14.9
Details

(2E)-3-(4-Bromophenyl)-1-(3-chlorophenyl)prop-2-en-1-one

Jerry P. Jasinski,^a ^* Ray J. Butcher,^b B. Narayana,^c K. Veena ^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, Manalaganotri, 574 199, India, and ^dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C₁₅H₁₀BrClO, the dihedral angle between mean planes of the bromo- and chloro-substituted benzene rings is 46.2 (2)° compared to 45.20 (9)° in the structure with the Cl substituent in the meta position of the aromatic ring. The dihedral angles between the mean plane of the prop-2-ene-1-one group and the mean planes of the 4-bromophenyl and 3-chlorophenyl rings are 28.7 (5) and 24.2 (4)°, respectively. In the crystal, weak intermolecular C-H [pi] interactions occur.

Related literature

For a related structure, see: Ng et al. (2006).

Experimental

Crystal data

C₁₅H₁₀BrClO
M_r = 321.59
Triclinic, $[P \overline 1]$
a = 5.9197 (8) Å
b = 7.3391 (11) Å
c = 14.8171 (17) Å
= 101.929 (11)°
= 94.371 (10)°
= 93.299 (11)°
V = 626.22 (15) Å³
Z = 2
Cu K radiation
= 6.29 mm^-1
T = 110 K
0.50 × 0.21 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini detector
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.041, T_max = 0.344
3868 measured reflections
2432 independent reflections
2312 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.058
wR(F²) = 0.164
S = 1.07
2432 reflections
163 parameters
H-atom parameters constrained
_max = 1.78 e Å^-3
_min = -1.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2A-H2AACg2ⁱ	0.95	2.97	3.588 (4)	124
C5A-H5AACg2ⁱⁱ	0.95	2.84	3.463 (4)	124
C12A-H12ACg1ⁱⁱⁱ	0.95	2.83	3.527 (4)	131
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y, -z+1; (iii) -x, -y+1, -z+1. Cg1 is the centroid of the C1A-C6A ring and Cg2 is the centroid of the C10A-C15A ring.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; 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: BT5130 ).

Acknowledgements

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

References

Ng, S.-L., Razak, I. A., Fun, H.-K., Shettigar, V., Patil, P. S. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o2175-o2177.
Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds