(2E)-3-(3-Benzyl­oxyphen­yl)-1-(2-hydroxy-5-methyl­phen­yl)prop-2-en-1-one

Hoong-Kun Fun; Suhana Arshad; B K Sarojini; V Musthafa Khaleel; B Narayana

doi:10.1107/S1600536811016977

. 2011 May 11;67(Pt 6):o1372–o1373. doi: 10.1107/S1600536811016977

(2E)-3-(3-Benzyloxyphenyl)-1-(2-hydroxy-5-methylphenyl)prop-2-en-1-one

Hoong-Kun Fun ^a,^*,^‡, Suhana Arshad ^a, B K Sarojini ^b, V Musthafa Khaleel ^b, B Narayana ^c

PMCID: PMC3120564 PMID: 21754763

Abstract

In the molecule of the title compound, C₂₃H₂₀O₃, an intramolecular O—H⋯O hydrogen bond generates an S(6) ring. The central benzene ring makes dihedral angles of 80.17 (8) and 16.99 (7)°, respectively, with the benzyloxy and hydroxymethyl phenyl rings. In the crystal, molecules are linked via intermolecular C—H⋯O hydrogen bonds to form dimers. The dimers are connected by C—H⋯O hydrogen bonds and C—H⋯π interactions to form columns down the b axis.

Related literature

For general background and applications of chalcones, see: Awad et al. (1960 ▶); Coudert et al. (1988 ▶); Insuasty et al. (1992 ▶, 1997 ▶); Kolos et al. (1996 ▶); Sarojini et al. (2006 ▶); Shettigar et al. (2010 ▶); Samshuddin et al. (2010 ▶); Fun et al. (2010 ▶). For related structures, see: Butcher et al. (2006 ▶); Ravishankar et al. (2003 ▶, 2005 ▶); Narayana et al. (2007 ▶); Sarojini, Narayana et al. (2007 ▶); Sarojini, Yathirajan et al. (2007 ▶); Sharma et al. (1997 ▶); Jasinski et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₃H₂₀O₃
M _r = 344.39
Triclinic,
a = 8.7308 (5) Å
b = 9.5721 (5) Å
c = 11.5286 (6) Å
α = 106.547 (1)°
β = 94.572 (1)°
γ = 101.671 (1)°
V = 894.74 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.42 × 0.37 × 0.28 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.966, T _max = 0.977
18270 measured reflections
5238 independent reflections
3853 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.163
S = 1.03
5238 reflections
240 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.23 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 datablocks global, I. DOI: 10.1107/S1600536811016977/ci5187sup1.cif

e-67-o1372-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016977/ci5187Isup2.hkl

e-67-o1372-Isup2.hkl^{(256.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811016977/ci5187Isup3.cml

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

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

Cg1 is the centroid of the C17–C22 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O3	0.93 (2)	1.65 (3)	2.521 (2)	155 (3)
C16—H16B⋯O3ⁱ	0.97	2.60	3.445 (2)	146
C22—H22A⋯O2ⁱⁱ	0.93	2.56	3.435 (2)	158
C11—H11A⋯Cg1ⁱⁱⁱ	0.93	2.80	3.660 (2)	153

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

Acknowledgments

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). SA thanks the Malaysian government and USM for the award of a research scholarship. VMK thanks P. A. College of Engineering for research facilities.

supplementary crystallographic information

Comment

Chalcones (1,3-diarylpropenones) have been widely used as starting materials in numerous synthetic reactions (Awad et al., 1960; Coudert et al., 1988) including the preparation of fused-ring heterocyclic compounds (Insuasty et al., 1992, 1997; Kolos et al., 1996; Samshuddin et al., 2010; Fun et al., 2010). Chalcones are also finding application as organic nonlinear optical materials (NLO) for their SHG conversion efficiency (Sarojini et al., 2006; Shettigar et al., 2010). The crystal structures of some of the related chalcones viz 1-(3,4-dimethoxyphenyl)-3-(3-methylphenyl)prop-2-en-1-one (Sharma et al., 1997), 3-(3,4-dimethoxyphenyl)-1-(4-hydroxy-phenyl)prop-2-en-1-one (Ravishankar et al., 2003), 1-(4-chlorophenyl)-3-(4-hydroxyphenyl) prop-2-en-1-one (Ravishankar et al., 2005), 3-(3,4-dimethoxyphenyl)-1- (4-fluorophenyl)prop-2-en-1-one (Butcher et al., 2006), 3-(2-chlorophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one (Narayana et al., 2007), (2E)-1-(2-hydroxyphenyl)-3-(4-methoxy-phenyl)prop-2-en-1-one, (2E)-1-(2-hydroxyphenyl)-3-[4-(methyl-sulfanyl)phenyl]prop-2-en-1-one (Sarojini, Narayana et al., 2007; Sarojini, Yathirajan et al., 2007) and (2E)-3- (3,4-dimethoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one (Jasinski et al., 2011) have been reported. In continuation to our studies on structures of chalcones, we report here the crystal structure of a new chalcone, the title compound.

In the molecular structure (Fig. 1), an intramolecular O2—H1O2···O3 hydrogen bond (Table 1) forming an S(6) ring motif (Bernstein et al., 1995) is observed. The C1–C6 and C10–C15 benzene rings form a dihedral angle of 16.99 (7)° between them. In addition, they also make dihedral angles of 69.01 (7) and 80.17 (8)°, respectively, with the terminal phenyl ring (C17–C22). Bond lengths (Allen et al., 1987) and angles are within normal range.

The crystal packing is shown in Fig. 2. The molecules are linked by intermolecular C22—H22A···O2 hydrogen bonds (Table 1) to form dimers. Furthermore, these dimers are connected by intermolecular C16—H16B···O3 hydrogen bonds (Table 1) to form columns down the b axis. The C—H···π interactions (Table 1) which involve C11 and the C17–C22 phenyl ring further stabilize the crystal structure.

Experimental

2-Hydroxy-5-methoxyacetophenone (1.66 g, 0.01 mol) was mixed with 4-benzyloxybenzaldehyde (2.12 g, 0.01 mol) and dissolved in ethanol (30 ml). To this solution, 3 ml of KOH (50%, 10 mL) was added at 5°C. The reaction mixture was stirred for 5 h and poured on to crushed ice. The pH of this mixture was adjusted to 3–4 with 2 M HCl aqueous solution. The resulting crude yellow solid was filtered, washed successively with dilute HCl solution and distilled water and finally recrystallized from ethanol (95%) to give the pure chalcone. Crystals suitable for X-ray diffraction studies were grown by slow evaporation of the solution of the compound in ethyl alcohol-DMF (4:1) mixture (m.p. 393–397 K). Composition: found (calculated) for C₂₃H₂₀O₃: C 76.65 (76.63), H 5.59 (5.57).