2,3-Dibromo-3-(4-chloro­phen­yl)-1-(2-hy­droxy­phen­yl)propan-1-one

Hoong-Kun Fun; Wan-Sin Loh; B K Sarojini; V Musthafa Khaleel; B Narayana

doi:10.1107/S1600536811036798

. 2011 Sep 17;67(Pt 10):o2651–o2652. doi: 10.1107/S1600536811036798

2,3-Dibromo-3-(4-chlorophenyl)-1-(2-hydroxyphenyl)propan-1-one

Hoong-Kun Fun ^a,^*,^‡, Wan-Sin Loh ^a,^§, B K Sarojini ^b, V Musthafa Khaleel ^b, B Narayana ^c

PMCID: PMC3201456 PMID: 22064869

Abstract

In the title molecule, C₁₅H₁₁Br₂ClO₂, an S(6) ring motif is formed via an intramolecular O—H⋯O hydrogen bond. The dihedral angle formed between the chloro- and hydroxy-substituted benzene rings is 34.10 (15)°. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link the molecules into chains along the c axis.

Related literature

For applications of chalcone compounds, see: Liu et al. (2003 ▶); Nielson et al. (1998 ▶); Rajas et al. (2002 ▶); Dinkova-Kostova et al. (1998 ▶); Goto et al. (1991 ▶); Uchida et al. (1998) ▶; Tam et al. (1989 ▶); Indira et al. (2002 ▶); Sarojini et al. (2006 ▶). For related structures, see: Butcher, Yathirajan, Anilkumar et al. (2006 ▶); Butcher, Yathirajan, Sarojini et al. (2006 ▶); Harrison et al. (2005 ▶); Yathirajan, Mayekar et al. (2007 ▶); Yathirajan, Vijesh et al. (2007 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₅H₁₁Br₂ClO₂
M _r = 418.51
Monoclinic,
a = 29.075 (3) Å
b = 9.2358 (10) Å
c = 11.4374 (12) Å
β = 103.290 (2)°
V = 2989.0 (6) Å³
Z = 8
Mo Kα radiation
μ = 5.60 mm⁻¹
T = 297 K
0.39 × 0.36 × 0.22 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.218, T _max = 0.379
16663 measured reflections
5375 independent reflections
3337 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.122
S = 1.04
5375 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811036798/lh5331sup1.cif

e-67-o2651-sup1.cif^{(17.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036798/lh5331Isup2.hkl

e-67-o2651-Isup2.hkl^{(263.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811036798/lh5331Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2	0.80	1.87	2.591 (3)	150
C11—H11A⋯O2ⁱ	0.93	2.53	3.416 (4)	160

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of a research fellowship. VMK thanks P. A. College of Engineering for research facilities.

supplementary crystallographic information

Comment

For a structurally simple group of compounds, chalcones display an impressive array of biological activities, among which antimalarial (Liu et al., 2003), antiprotozoal (Nielson et al., 1998), nitric oxide inhibition (Rajas et al., 2002) and anticancer activities (Dinkova-Kostova et al., 1998) have been reported in the literature. Among several organic compounds reported for non-linear optical (NLO) properties, chalcone derivatives are notable materials for their excellent blue light transmittance and good crystallizability. They provide a necessary configuration to show NLO properties, with two planar rings connected through a conjugated double bond (Goto et al., 1991; Uchida et al., 1998; Tam et al., 1989; Indira et al., 2002; Sarojini et al., 2006). The substitution of a bromo group on either of the phenyl rings can influence the non-centrosymmetric crystal packing. The bromo group can obviously improve the molecular first-order hyperpolarizabilities and can effectively reduce dipole-dipole interactions between the molecules. Chalcone derivatives usually have a lower melting temperature, which can be a drawback when we use these crystals in optical instruments. Chalcone dibromides usually have higher melting points and are thermally stable. Only a few structures of these compounds have been reported (Butcher, Yathirajan, Anilkumar et al., 2006; Butcher, Yathirajan, Sarojini et al.,2006; Harrison et al., 2005; Yathirajan, Mayekar et al., 2007; Yathirajan, Vijesh et al., 2007). In continuation to our studies on crystal structures of chalcones, we report the synthesis and crystal structure of the title compound.

In the title compound (Fig. 1), an S(6) ring motif (Bernstein et al., 1995) is formed via the intramolecular O1—H1O1···O2 hydrogen bond (Table 1). The dihedral angle formed between the chloro-substituted benzene ring (C1–C6) and hydroxy-substituted benzene ring (C10–C15) is 34.10 (15)°.

In the crystal packing (Fig. 2), intermolecular C11—H11A···O2ⁱ hydrogen bonds (Table 1) link the molecules into chains along the c axis.

Experimental

(2E)-1-(2-Hydroxyphenyl)-3-(4-chlorophenyl)prop-2-en-1-one (0.01 mol) was treated with bromine in acetic acid (30%) until the orange colour of the solution persisted. After stirring for half an hour, the contents were poured onto crushed ice. The resulting solid mass was collected by filtration. The compound was dried and recrystallized from ethanol. Crystals suitable for structure determination were obtained from acetone by slow evaporation (m. p. = 395–397 K). Composition: Found (Calculated) for C₁₅H₁₁Br₂ClO₂, C: 43.19 (43.05); H: 2.68 (2.65).