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

Fun, H.-K.; Arshad, S.; Sarojini, B.K.; Khaleel, V.M.; Narayana, B.

doi:10.1107/S1600536811016977

Volume 67
Part 6
Pages o1372-o1373
June 2011

Received 28 April 2011
Accepted 5 May 2011
Online 11 May 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.049
wR = 0.163
Data-to-parameter ratio = 21.8
Details

(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 and B. Narayana ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,^bDepartment of Chemistry, P. A. College of Engineering, Mangalore 574 153, India, and ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
Correspondence e-mail: hkfun@usm.my

In the molecule of the title compound, C₂₃H₂₀O₃, an intramolecular O-HO 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-HO hydrogen bonds to form dimers. The dimers are connected by C-HO hydrogen bonds and C-H [pi] 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, $[P \overline 1]$
a = 8.7308 (5) Å
b = 9.5721 (5) Å
c = 11.5286 (6) Å
= 106.547 (1)°
= 94.572 (1)°
= 101.671 (1)°
V = 894.74 (8) Å³
Z = 2
Mo K radiation
= 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 > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.163
S = 1.03
5238 reflections
240 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.26 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C17-C22 ring.

D-HA	D-H	HA	DA	D-HA
O2-H1O2O3	0.93 (2)	1.65 (3)	2.521 (2)	155 (3)
C16-H16BO3ⁱ	0.97	2.60	3.445 (2)	146
C22-H22AO2ⁱⁱ	0.93	2.56	3.435 (2)	158
C11-H11ACg1ⁱⁱⁱ	0.93	2.80	3.660 (2)	153
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -z; (iii) x, y-1, z.

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 data and figures for this paper are available from the IUCr electronic archives (Reference: CI5187 ).

Acknowledgements

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.

References

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organic compounds