rac-2-Bromo-3-eth­oxy-1,3-bis­(4-methoxy­phen­yl)propan-1-one

Hoong-Kun Fun; Samuel Robinson Jebas; Jyothi N Rao; B Kalluraya

doi:10.1107/S1600536808039238

. 2008 Dec 3;65(Pt 1):o19. doi: 10.1107/S1600536808039238

rac-2-Bromo-3-ethoxy-1,3-bis(4-methoxyphenyl)propan-1-one

Hoong-Kun Fun ^a,^*, Samuel Robinson Jebas ^a,^‡, Jyothi N Rao ^b, B Kalluraya ^b

PMCID: PMC2967939 PMID: 21581644

Abstract

In the racemic (S,S/R,R) title compound, C₁₉H₂₁BrO₄, the two benzene rings are almost coplanar to each other, forming a dihedral angle of 3.58 (10)°. The crystal packing is strengthened by intermolecular Br—O [2.9800 (16) Å] short contacts, which link the molecules into infinite one-dimensional chains along [001].

Related literature

For the pharmacological applications of chalcones, see: Di Carlo et al. (1999 ▶); Dimmock et al. (1999 ▶); Go et al. (2005 ▶); Kalluraya et al. (1994 ▶); Rai et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₉H₂₁BrO₄
M _r = 393.27
Monoclinic,
a = 12.2734 (10) Å
b = 15.3432 (12) Å
c = 10.4381 (8) Å
β = 114.399 (4)°
V = 1790.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.31 mm⁻¹
T = 100.0 (1) K
0.55 × 0.38 × 0.19 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.351, T _max = 0.644
22919 measured reflections
5229 independent reflections
4345 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.103
S = 1.09
5229 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 1.15 e Å⁻³
Δρ_min = −1.21 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039238/dn2408sup1.cif

e-65-00o19-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039238/dn2408Isup2.hkl

e-65-00o19-Isup2.hkl^{(250.9KB, hkl)}

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

Acknowledgments

FHK and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a post–doctoral research fellowship. HKF also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

supplementary crystallographic information

Comment

Chalcones, one of the major classes of natural products with widespread distribution in fruits, vegetables, spices, tea and soy based foodstuff, have recently been the subject of great interest for their interesting pharmacological activities (Di Carlo et al., 1999). Chalcones and its derivatives have been reported to possess many useful properties including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities (Dimmock et al., 1999; Go et al., 2005). Monobromo chalcones are used in the formation of many heterocyclic compounds having multiple applications (Kalluraya et al., 1994; Rai et al., 2007). Due to these varied applications, we have synthesized a new α-bromo chalcone and report its crystal structure.

Bond lengths and angles in (I) (Fig. 1) are found to have normal values (Allen et al., 1987). There are two chiral centres C7 and C8 in the molecular structure therefore the centrosymmetic crystal is a racemate. The dihedral angle formed by the phenyl (C1—C6; C10—C15) rings is 3.58 (10)°, indicating that they are almost coplanar to each other.

The crystal packing is strengthened by intermolecular Br···Oⁱ=2.9800 (16)Å [symmetry code: X,1/2-Y,-1/2+Z] short contact. In the crystal packing, the molecules are linked into infinite one-dimensional chains along the [001] direction (Fig 2).

Experimental

1,3-Di(p-anisyl)-2,3-dibromopropane (0.01 mol) when treated with ethanol(25 mL) at room temperature in presence of triethyl amine (0.02 mol) resulted in the formation of the title compound involving a nucleophilic substitution reaction.