1-(2-Hy­droxy-5-methyl­phen­yl)-3-(2-methyl­phen­yl)prop-2-en-1-one

D Vijay Kumar; G B Thippeswamy; B S Jayashree; M A Sridhar

doi:10.1107/S1600536811018381

. 2011 May 25;67(Pt 6):o1492. doi: 10.1107/S1600536811018381

1-(2-Hydroxy-5-methylphenyl)-3-(2-methylphenyl)prop-2-en-1-one

D Vijay Kumar ^a, G B Thippeswamy ^b, B S Jayashree ^a, M A Sridhar ^b,^*

PMCID: PMC3120591 PMID: 21754860

Abstract

In the title compound, C₁₇H₁₆O₂, the dihedral angle between the aromatic rings is 5.12 (13)° and an intramolecular O—H⋯O hydrogen bond generates an S(6) ring.

Related literature

For a related structure and background references to chalcones, see: Thippeswamy et al. (2011 ▶).

Experimental

Crystal data

C₁₇H₁₆O₂
M _r = 252.30
Orthorhombic,
a = 13.3930 (11) Å
b = 14.1740 (16) Å
c = 14.5710 (15) Å
V = 2766.0 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.29 × 0.27 × 0.25 mm

Data collection

MacScience DIPLabo 32001 diffractometer
8036 measured reflections
2422 independent reflections
1654 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.073
wR(F ²) = 0.209
S = 1.15
2422 reflections
175 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: XPRESS (MacScience, 2002 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018381/hb5868sup1.cif

e-67-o1492-sup1.cif^{(17.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018381/hb5868Isup2.hkl

e-67-o1492-Isup2.hkl^{(119.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811018381/hb5868Isup3.cml

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
O18—H18⋯O11	0.82	1.89	2.608 (3)	146

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Acknowledgments

The authors are grateful to the DST/CSIR, New Delhi, and the University of Mysore for financial support and duly acknowledge Manipal College of Pharmaceutical Sciences for providing facilities to carry out the synthetic work.

supplementary crystallographic information

Comment

As part of our ongoing structural studies of chalcones (Thippeswamy et al., 2011), we now report the synthesis and crystal structure of the title compound, (I), (Fig. 1).

The title compound, C₁₇H₁₆O₂, consists of two methylphenyl rings attached at ei-ther sides of the propanone chain. The propanone unit is planar, which is confirmed by the r.m.s. deviation of 0.003 (3)Å from the mean plane. The dihedral angle between the least squares planes of 5-methylphenyl ring and 2-methylphenyl ring is 5.93 (13)° which indicates that 5-methylphenyl ring in +Syn-periplanar conformation with 2-methylphenyl ring. The bond lengths C1—O11, C1—C12, C1—C2, C2—C3, C3—C4 and bond angles C1—C2—C12,C1—C2—C3 are in good agreement with these of a similar compound reported earlier (Thippeswamy et al., 2011). The angles C2—C1—O11, C12—C1—O11 and C2—C1—C12 are 119.5 (2)°, 119.4 (2)° and 121.1 (2)° respectively which indicate that the position of C1 atom is nearly in trigonal geometry. An intramolecular O—H···O hydrogen bond occurs (Table 1).

Experimental

The title compound was prepared by dissolving 2-hydroxy-5- methoxyacetophenone 0.05 m mol in 15 ml of ethanol taken in a conical flask. To this 5 ml of 20° aqueous sodium hydroxide was added and kept for stirring at room temperature. To this mixture, 4-methylbenzaldehyde 0.05 m mol was added and continued stirring till the completion of reaction. The progress of the reaction was monitored by TLC using n-hexane and ethylacetate as solvent system. After completion of the reaction, the mixture was poured into ice cold water, mixed properly and acidified with dilute hydrochloric acid. The title compound separates as precipitate which was collected by filtration and crystallized from methanol as orange blocks of (I).