(2E)-1-(3-Bromo­phen­yl)-3-(6-meth­oxy-2-naphth­yl)prop-2-en-1-one

William T A Harrison; A N Mayekar; H S Yathirajan; B Narayana

doi:10.1107/S1600536810035117

. 2010 Sep 11;66(Pt 10):o2552. doi: 10.1107/S1600536810035117

(2E)-1-(3-Bromophenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one

William T A Harrison ^a,^*, A N Mayekar ^b,^c, H S Yathirajan ^b, B Narayana ^d

PMCID: PMC2983307 PMID: 21587540

Abstract

In the title compound, C₂₀H₁₅BrO₂, the prop-2-en-1-one fragment is substantially twisted [C—C—C—O = 23.0 (11)°]. The dihedral angle between the benzene and naphthalene rings is 44.28 (13)°. The only possible directional interactions in the crystal are weak C—H⋯π contacts, which generate (001) sheets.

Related literature

For related structures, see: Yathirajan et al. (2007a ▶,b ▶); Jasinski et al. (2009 ▶). For background to the non-linear optical properties of chalcones, see: Sarojini et al. (2006 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₀H₁₅BrO₂
M _r = 367.23
Orthorhombic,
a = 14.0955 (14) Å
b = 6.1295 (6) Å
c = 36.119 (4) Å
V = 3120.6 (5) Å³
Z = 8
Mo Kα radiation
μ = 2.64 mm⁻¹
T = 120 K
0.11 × 0.09 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T _min = 0.760, T _max = 0.925
28579 measured reflections
3545 independent reflections
1719 reflections with I > 2σ(I)
R _int = 0.228

Refinement

R[F ² > 2σ(F ²)] = 0.082
wR(F ²) = 0.163
S = 1.05
3545 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶), SCALEPACK and SORTAV (Blessing, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035117/tk2699sup1.cif

e-66-o2552-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035117/tk2699Isup2.hkl

e-66-o2552-Isup2.hkl^{(173.9KB, hkl)}

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

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

Cg2 is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cg2ⁱ	0.95	2.70	3.432 (6)	134
C7—H7⋯Cg2ⁱⁱ	0.95	2.80	3.520 (6)	134

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

ANM thanks the University of Mysore for providing research facilities. HSY thanks the University of Mysore for sanctioning sabbatical leave.

supplementary crystallographic information

Comment

The title compound, (I), (Fig. 1), was prepared as part of our ongoing studies (Yathirajan et al., 2007a,b; Jasinski et al., 2009) of substituted phenyl/naphthyl chalcone derivatives as possible candidates for non-linear optical materials (Sarojini et al., 2006). However, (I) crystallizes in a centrosymmetric space group, thus its second-harmonic generation (SHG) response must be zero.

The prop-2-en-1-one (enone) fragment in (I) is substantially twisted, as indicated by the C11—C12—C13—O2 torsion angle of 23.0 (11)°. The dihedral angle between the aromatic ring systems is 44.28 (13)°. Equivalent data for related structures are as follows: (2E)-1-(2,4-dichlorophenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one (Yathirajan et al., 2007a): -10.9 (2) and 44.94 (4)°; (2E)-3-(6-methoxy-2-naphthyl)-1-phenylprop-2-en-1-one (Yathirajan et al., 2007b): -15.9 (4) and 14.9 (8)°; (2E)-1-(2-hydroxyphenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one (Jasinski et al., 2009): -14.9 (2) and 31.7 (3)°. Otherwise, the bond lengths for (I) fall within their expected ranges (Allen et al., 1987).

In the crystal of (I), the only possible directional interactions between molecules are weak C—H···π contacts in which the C3–C8 ring of the naphthyl moiety provides both the C—H donor groups and the aromatic acceptor surface (Table 1, Fig. 2). Together, these generate (001) sheets.

Experimental

To a thoroughly stirred solution of 6-methoxy-2-naphthaldehyde (1.86 g, 0.01 mol) and 3-bromoacetophenone (1.99 g, 0.01 mol) in 25 ml methanol, 5 ml of 40% KOH solution was added. The reaction mixture was stirred overnight and the solid separated was collected by filtration. The product obtained was recrystallized from methanol. Colourless slabs of (I) were grown by the slow evaporation of the ethylacetate solution (m.p. 427–429 K).