2,3-Dibromo-1,3-bis­(4-fluoro­phen­yl)propan-1-one

Jasinski, J.P.; Guild, C.J.; Samshuddin, S.; Narayana, B.; Yathirajan, H.S.

doi:10.1107/S1600536810026905

Volume 66
Part 8
Page o2018
August 2010

Received 4 July 2010
Accepted 7 July 2010
Online 14 July 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.031
wR = 0.079
Data-to-parameter ratio = 22.1
Details

2,3-Dibromo-1,3-bis(4-fluorophenyl)propan-1-one

Jerry P. Jasinski,^a ^* Curtis J Guild,^a S. Samshuddin,^b B. Narayana ^b and H. S. Yathirajan ^c

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

In the title compound, C₁₅H₁₀Br₂F₂O, the dihedral angle between the two 3-fluoro-substituted benzene rings is 5.7 (5)°. The two bromine substituents on the chalcone moiety are close to anti as the Br-C-C-Br torsion angle is 176.9 (7)°. Weak C-Br [pi] interactions may contribute to the crystal stability.

Related literature

For bromo substitution of non-linerar optical (NLO) compounds, see: Uchida et al. (1998); Tam et al. (1989); Indira et al. (2002). For NLO first-order hyperpolarizabilities, see: Zhao et al. (2002). For related structures, see: Narayana et al. (2007); Sarojini et al. (2007); Yathirajan et al. (2007); Butcher et al. (2006).

Experimental

Crystal data

C₁₅H₁₀Br₂F₂O
M_r = 404.05
Triclinic, $[P \overline 1]$
a = 5.7381 (13) Å
b = 9.909 (2) Å
c = 12.575 (3) Å
= 75.324 (3)°
= 87.472 (3)°
= 82.300 (3)°
V = 685.4 (3) Å³
Z = 2
Mo K radiation
= 5.93 mm^-1
T = 100 K
0.55 × 0.30 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.329, T_max = 0.746
8841 measured reflections
4008 independent reflections
3408 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.079
S = 1.21
4008 reflections
181 parameters
H-atom parameters constrained
_max = 1.08 e Å^-3
_min = -0.87 e Å^-3

Table 1
Y-XCg interactions (Å)

Cg1 and Cg2 are the centroids of the C1-C6 and C10-C15 rings, respectively.

Y-XCg	XCg	YCg	Y-XCg
C8-Br1Cg1ⁱ	3.650 (7)	5.617 (2)	174
C7-Br3Cg2ⁱⁱ	3.479 (6)	5.341 (1)	153
Symmetry codes: (i) -x, 1 - y, 1 - z; (ii) 1 - x, 1 - y, -z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2690 ).

Acknowledgements

JPJ thanks Dr Matthias Zeller and the YSU Department of Chemistry for their assistance with the data collection. The diffractometer was funded by NSF grant 0087210, by Ohio Board of Regents grant CAP-491, and by YSU. SS thanks Mangalore University and the UGC SAP for financial assistance for the purchase of chemicals. HSY thanks the UOM for sabbatical leave.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Butcher, R. J., Yathirajan, H. S., Sarojini, B. K., Narayana, B. & Mithun, A. (2006). Acta Cryst. E62, o1629-o1630.
Indira, J., Karat, P. P. & Sarojini, B. K. (2002). J. Cryst. Growth, 242, 209-214.
Narayana, B., Mayekar, A. N., Yathirajan, H. S., Sarojini, B. K. & Kubicki, M. (2007). Acta Cryst. E63, o4362.
Sarojini, B. K., Narayana, B., Yathirajan, H. S., Mayekar, A. N. & Bolte, M. (2007). Acta Cryst. E63, o3755.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tam, W., Guerin, B., Calabrese, J. C. & Stevenson, S. H. (1989). Chem. Phys. Lett. 154, 93-96.
Uchida, T., Kozawa, K., Sakai, T., Aoki, M., Yoguchi, H., Abduryim, A. & Watanabe, Y. (1998). Mol. Cryst. Liq. Cryst. 315, 135-140.
Yathirajan, H. S., Vijesh, A. M., Narayana, B., Sarojini, B. K. & Bolte, M. (2007). Acta Cryst. E63, o2198-o2199.
Zhao, B., Lu, W. Q., Zhou, Z. H. & Wu, Y. (2002). J. Mater. Chem. 10, 1513-1517.

organic compounds