(2E)-3-[3-(Benz­yloxy)phen­yl]-1-(2-hy­droxy­phen­yl)prop-2-en-1-one

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

doi:10.1107/S160053681101614X

. 2011 May 7;67(Pt 6):o1313–o1314. doi: 10.1107/S160053681101614X

(2E)-3-[3-(Benzyloxy)phenyl]-1-(2-hydroxyphenyl)prop-2-en-1-one

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

PMCID: PMC3120523 PMID: 21754713

Abstract

In the title compound, C₂₂H₁₈O₃, an intramolecular O—H⋯O hydrogen bond stabilizes the molecular structure, forming an S(6) ring motif. The central benzene ring forms a dihedral angle of 64.74 (5)° with the phenyl ring and a dihedral angle of 5.58 (5)° with the terminal benzene ring. In the crystal, molecules are linked into columns along the a axis via intermolecular C—H⋯O hydrogen bonds. C—H⋯π interactions involving the centroid of the hydroxy-substituted benzene ring further stabilize the crystal structure.

Related literature

For the background to chalcones, see: Awad et al. (1960 ▶); Coudert et al. (1988 ▶); Insuasty et al. (1992 ▶, 1997 ▶); Kolos et al. (1996 ▶); Samshuddin et al. (2010 ▶); Fun et al. (2010 ▶); Sarojini et al. (2006 ▶); Shettigar et al. (2010 ▶); Sharma et al. (1997 ▶); Ravishankar et al. (2003 ▶, 2005 ▶); Butcher et al. (2006 ▶); Narayana et al. (2007 ▶); Sarojini et al. (2007a ▶,b ▶); Jasinski et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₂H₁₈O₃
M _r = 330.36
Monoclinic,
a = 6.6343 (1) Å
b = 35.7706 (5) Å
c = 8.1537 (1) Å
β = 121.879 (1)°
V = 1643.12 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.46 × 0.41 × 0.28 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.960, T _max = 0.976
23662 measured reflections
5994 independent reflections
5154 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.126
S = 1.04
5994 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.21 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/S160053681101614X/sj5129sup1.cif

e-67-o1313-sup1.cif^{(20.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101614X/sj5129Isup2.hkl

e-67-o1313-Isup2.hkl^{(293.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681101614X/sj5129Isup3.cml

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

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

Cg is the centroid of the C17–C22 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1⋯O2	0.96	1.62	2.5121 (11)	152
C5—H5A⋯O3ⁱ	0.93	2.47	3.3912 (13)	170
C18—H18A⋯O3ⁱⁱ	0.93	2.48	3.1235 (16)	127
C7—H7B⋯Cg1ⁱ	0.97	2.75	3.6633 (11)	158

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

Acknowledgments

The authors 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 the 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 et al., 2007a,b) and (2E)-3-(2-anthryl)-1-(2-hydroxyphenyl)prop-2-en-1-one (Jasinski et al., 2011) have been reported. In a continuation of our studies of the structures of chalcones, we report the crystal structure of a new chalcone, (2E)-3-(3-benzyloxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one, C₂₂H₁₈O₃, (I).

The molecular strucure of (I) is shown in Fig. 1. An intramolecular O3—H1···O2 hydrogen bond (Table 1) stabilized the molecular structure, forming an S(6) ring motif (Bernstein et al., 1995). The (C8–C13) benzene ring forms a dihedral angle of 64.74 (5)° with the C1–C6 phenyl ring and is almost co-planar with the C17–C22 phenyl ring with a dihedral angle of 5.58 (5)°. Bond lengths (Allen et al., 1987) and angles are within the normal ranges.

In the crystal packing (Fig. 2), the molecules are linked into columns along the a axis via intermolecular C5—H5A···O3 and C18—H18A···O3 hydrogen bonds (Table 1). C–H···π interactions (Table 1) involving the centroids of C17–C22 rings (Cg1) further stabilize the crystal structure.

Experimental

2-Hydroxyacetophenone (1.36 g, 0.01 mol) was mixed with 4-benzyloxybenzaldehyde (2.12 g, 0.01 mol) and dissolved in ethanol (40 ml). To this solution 4 ml of KOH (50%) was added at 278 K. The reaction mixture was stirred for 8 h and poured onto 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 the slow evaporation of the solution of the compound in ethyl alcohol (m. p.: 367–369 K). Composition: Found (calculated) for C₂₂H₁₈O₃, C 79.98 (79.93); H: 5.49 (5.52).