(E)-3-[4-(Dodec­yloxy)phen­yl]-1-(2-hydroxy­phen­yl)prop-2-en-1-one

Razak, I.A.; Fun, H.-K.; Ngaini, Z.; Fadzillah, S.M.H.; Hussain, H.

doi:10.1107/S1600536809014925

Volume 65
Part 5
Pages o1133-o1134
May 2009

Received 1 April 2009
Accepted 22 April 2009
Online 25 April 2009

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.005 Å
R = 0.069
wR = 0.206
Data-to-parameter ratio = 15.7
Details

(E)-3-[4-(Dodecyloxy)phenyl]-1-(2-hydroxyphenyl)prop-2-en-1-one

Ibrahim Abdul Razak,^a ^*⁺ Hoong-Kun Fun,^a ⁺⁺ Zainab Ngaini,^b Siti Muhaini Haris Fadzillah ^b and Hasnain Hussain ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,^bDepartment of Chemistry, Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia, and ^cDepartment of Molecular Biology, Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia
Correspondence e-mail: arazaki@usm.my

In the title compound, C₂₇H₃₆O₃, the asymmetric unit consists of two crystallographically independent molecules. The aromatic rings form dihedral angles of 17.1 (2) and 17.6 (2)° in the two molecules. In both molecules, the enone groups adopt an s-cis conformation and the alkoxyl chains are in trans conformations curving out of the zigzag plane. Intramolecular O-HO hydrogen bonds involving the keto and hydroxy groups generate S(6) ring motifs. The molecules are stacked alternately in a head-to-tail fashion along the a axis and the crystal structure is stabilized by weak C-H [pi] interactions. The crystal studied was a non-merohedral twin, the ratio of components being 0.788 (2):0.212 (2).

Related literature

For general background to the biological activity of chalcone derivatives, see: Bhat et al. (2005); Xue et al. (2004); Satyanarayana et al. (2004); Zhao et al. (2005); Lee et al. (2006). For related structures, see: Ng et al. (2006); Razak et al. (2009); Ngaini, Fadzillah et al. (2009); Ngaini, Rahman et al. (2009). For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₂₇H₃₆O₃
M_r = 408.56
Triclinic, $[P \overline 1]$
a = 7.4953 (6) Å
b = 13.4714 (9) Å
c = 23.7874 (18) Å
= 75.116 (4)°
= 83.876 (5)°
= 84.669 (5)°
V = 2302.7 (3) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 100 K
0.55 × 0.13 × 0.06 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.960, T_max = 0.996
8571 measured reflections
8571 independent reflections
4737 reflections with I > 2(I)

Refinement

R[F² > 2(F²)] = 0.069
wR(F²) = 0.206
S = 1.03
8571 reflections
546 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1A-H1AO2A	0.82	1.79	2.513 (4)	146
O1B-H1BO2B	0.82	1.81	2.530 (4)	146
C22B-H22CCg1ⁱ	0.97	2.77	3.654 (4)	151
C17B-H17DCg2	0.97	2.82	3.612 (4)	139
C22A-H22BCg3	0.97	2.93	3.765 (4)	145
Symmetry code: (i) x-1, y, z. Cg1, Cg2 and Cg3 are the centroids of the C1A--C6A, C10A-C15A and C1B-C6B rings, respectively.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2802 ).

Acknowledgements

HKF and IAR thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312 and for the Research University Golden Goose grant No. 1001/PFIZIK/811012. ZN and HH thank Universiti Malaysia Sarawak for the Geran Penyelidikan Dana Khas Inovasi, grant No. DI/01/2007(01). SMHF thanks Malaysian Government and Universiti Malaysia Sarawak for providing a scholarship for postgraduate studies.

References

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organic compounds