(E)-3-(3,4-Dimeth­oxy­phen­yl)-1-(2-hy­droxy­phen­yl)prop-2-en-1-one

Jerry P Jasinski; Ray J Butcher; V Musthafa Khaleel; B K Sarojini; H S Yathirajan

doi:10.1107/S1600536811008361

. 2011 Mar 12;67(Pt 4):o845. doi: 10.1107/S1600536811008361

(E)-3-(3,4-Dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one

Jerry P Jasinski ^a,^*, Ray J Butcher ^b, V Musthafa Khaleel ^c, B K Sarojini ^c, H S Yathirajan ^d

PMCID: PMC3099868 PMID: 21754127

Abstract

In the title compound, C₁₇H₁₆O₄, the dihedral angle between the mean planes of the hydroxyphenyl and dimethoxyphenyl rings is 5.9 (6)°. The mean plane of the prop-2-en-1-one group makes dihedral angles of 3.6 (0) and 2.6 (7)° with the hydroxyphenyl and dimethoxyphenyl rings, respectively. An intramolecular O—H⋯O hydrogen bond occurs. The crystal packing is stabilized by weak intermolecular C—H⋯O contacts and π–π stacking interactions [centroid–centroid distance = 3.6571 (8) Å].

Related literature

For related structures, see: Butcher et al. (2006 ▶); Cao et al. (2005 ▶); Harrison et al. (2007 ▶); Jasinski et al. (2010 ▶, 2011a ▶,b ▶); Ngaini et al. (2009 ▶); Radha Krishna et al. (2005 ▶); Sharma et al. (1997 ▶); Wu et al. (2005 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₇H₁₆O₄
M _r = 284.30
Monoclinic,
a = 14.2315 (2) Å
b = 8.0292 (1) Å
c = 13.6027 (2) Å
β = 110.0531 (14)°
V = 1460.11 (3) Å³
Z = 4
Cu Kα radiation
μ = 0.76 mm⁻¹
T = 295 K
0.51 × 0.47 × 0.35 mm

Data collection

Oxford Diffraction Gemini R diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.065, T _max = 1.000
6676 measured reflections
3014 independent reflections
2336 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.152
S = 1.12
3014 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008361/kp2312sup1.cif

e-67-0o845-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008361/kp2312Isup2.hkl

e-67-0o845-Isup2.hkl^{(147.9KB, hkl)}

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—H1A⋯O2	0.82	1.77	2.5021 (18)	147
C14—H14A⋯O2ⁱ	0.93	2.51	3.4250 (19)	170

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Symmetry code: (i) Inline graphic .

Acknowledgments

BKS thanks the BRNS, DAE, Government of India (grant No. 2008/34/05-BRNS/457). VMK thanks P·A. College of Engineering for the research facilities. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

Comment

In continuation to our studies on crystal structures of chalcones (Jasinski et al., 2010, 2011a, 2011b), we report here the synthesis (Fig. 1) and crystal structure of a new chalcone, C₁₇H₁₆O₄, (I). The dihedral angle between the mean planes of the hydroxyphenyl and dimethoxyphenyl rings is 5.9 (6)° (Fig. 2). The mean plane of the prop-2-en-1-one group, the active site in this molecule, makes angles of 3.6 (0)° and 2.6 (7)°, respectively, with the hydroxyphenyl and dimethoxyphenyl rings. Bond lengths and angles are normal (Allen et al., 1987) and corespond to those observed in related compounds (Butcher et al., 2006; Cao et al., 2005; Harrison et al., 2007; Jasinski et al., 2010, 2011a, 2011b; Ngaini et al., 2009; Radha Krishna et al., 2005; Sharma et al., 1997; Wu et al., 2005). Crystal packing is stabilized by O—H···O intramolecular hydrogen bonds, weak C—H···O intermolecular (Table 1) and π—π stacking interactions (Table 2, Fig. 3).

Experimental

2-Hydroxyacetophenone (1.36 g, 0.01 mol) was mixed with 3,4-dimethoxybenzaldehyde (1.66 g, 0.01 mol) and dissolved in ethanol (40 ml) (Fig. 1). To this solution, 5 mL of KOH (50%) was added at 278 K. The reaction mixture stirred overnight at room temperature 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 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.: 378–381 K). Composition: Found (Calculated) for C₁₇H₁₆O₄, C 75.25 (75.28); H: 5.98 (5.92).