5-Hy­droxy-6-[(E)-2-phenyl­ethen­yl]-5,6-dihydro-2H-pyran-2-one isolated from Goniothalamus ridleyi

Jusoh, S.; Din, L.B.; Zakaria, Z.; Khaledi, H.

doi:10.1107/S1600536812028334

Volume 68
Part 7
Page o2274
July 2012

Received 14 June 2012
Accepted 22 June 2012
Online 30 June 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.027
wR = 0.069
Data-to-parameter ratio = 8.4
Details

5-Hydroxy-6-[(E)-2-phenylethenyl]-5,6-dihydro-2H-pyran-2-one isolated from Goniothalamus ridleyi

Samsiah Jusoh,^a Laily B. Din,^a Zuriati Zakaria ^a and Hamid Khaledi ^b ^*

^aSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, National University of Malaysia, 43600 UKM Bangi, Selangor, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: hamid.khaledi@gmail.com

In the title compound, C₁₃H₁₂O₃, the pyran ring adopts a half-chair conformation with a C atom deviating from the least-squares plane of the remaining ring atoms by 0.606 (2) Å. This plane and that of the benzene ring make a dihedral angle of 44.18 (6)°. In the crystal, molecules are linked through O-HO hydrogen bonds into infinite chains along the b axis, and these chains are cross-linked by C-HO hydrogen bonded into sheets lying parallel to the bc plane. The layers are further connected via C-H [pi] interactions to form a three-dimensional supramolecular structure.

Related literature

For spectroscopic characterization of the 5 [beta] -hydroxygoniothalamin, see: Goh et al. (1995). For the crystal structures of some similar compounds, see: Fun et al. (1995); Tuchinda et al. (2006).

Experimental

Crystal data

C₁₃H₁₂O₃
M_r = 216.23
Monoclinic, P 2₁
a = 6.5442 (8) Å
b = 11.0267 (14) Å
c = 8.0991 (10) Å
= 111.402 (2)°
V = 544.14 (12) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 100 K
0.30 × 0.18 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.973, T_max = 0.994
2559 measured reflections
1250 independent reflections
1220 reflections with I > 2(I)
R_int = 0.012

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.069
S = 1.08
1250 reflections
148 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.18 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1-C6 ring.

D-HA	D-H	HA	DA	D-HA
O1-H1AO2ⁱ	0.87 (3)	1.95 (3)	2.8026 (19)	170 (2)
C12-H12O1ⁱⁱ	0.95	2.53	3.427 (2)	157
C9-H9Cgⁱⁱ	1.00	2.97	3.747 (2)	135
C10-H10Cgⁱⁱⁱ	1.00	2.80	3.6561 (18)	144
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z]$ ; (ii) x-1, y, z; (iii) $[-x+2, y-{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2562 ).

Acknowledgements

This research was financially supported by UKM grant (grant No. UKM-DLP-2012-033). We are grateful to Dr Shamsul Khamis for the assistance in identifying plant material.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Fun, H.-K., Sivakumar, K., Ang, H.-B., Sam, T.-W. & Gan, E.-K. (1995). Acta Cryst. C51, 1330-1333.
Goh, S. H., Ee, G. C. L. & Chuah, C. H. (1995). Nat. Prod. Lett. 5, 255-259.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tuchinda, P., Munyoo, B., Pohmakotr, M., Thinapong, P., Sophasan, S., Santisuk, T. & Reutrakul, V. (2006). J. Nat. Prod. 69, 1728-1733.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds