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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 [sigma](C-C) = 0.003 Å
R = 0.027
wR = 0.069
Data-to-parameter ratio = 8.4
Details
Open access

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

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-H...O hydrogen bonds into infinite chains along the b axis, and these chains are cross-linked by C-H...O 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[Goh, S. H., Ee, G. C. L. & Chuah, C. H. (1995). Nat. Prod. Lett. 5, 255-259.]). For the crystal structures of some similar compounds, see: Fun et al. (1995[Fun, H.-K., Sivakumar, K., Ang, H.-B., Sam, T.-W. & Gan, E.-K. (1995). Acta Cryst. C51, 1330-1333.]); Tuchinda et al. (2006[Tuchinda, P., Munyoo, B., Pohmakotr, M., Thinapong, P., Sophasan, S., Santisuk, T. & Reutrakul, V. (2006). J. Nat. Prod. 69, 1728-1733.]).

[Scheme 1]

Experimental

Crystal data
  • C13H12O3

  • Mr = 216.23

  • Monoclinic, P 21

  • a = 6.5442 (8) Å

  • b = 11.0267 (14) Å

  • c = 8.0991 (10) Å

  • [beta] = 111.402 (2)°

  • V = 544.14 (12) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.973, Tmax = 0.994

  • 2559 measured reflections

  • 1250 independent reflections

  • 1220 reflections with I > 2[sigma](I)

  • Rint = 0.012

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
O1-H1A...O2i 0.87 (3) 1.95 (3) 2.8026 (19) 170 (2)
C12-H12...O1ii 0.95 2.53 3.427 (2) 157
C9-H9...Cgii 1.00 2.97 3.747 (2) 135
C10-H10...Cgiii 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[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


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.  [CrossRef] [ChemPort]
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.  [CrossRef] [details]
Goh, S. H., Ee, G. C. L. & Chuah, C. H. (1995). Nat. Prod. Lett. 5, 255-259.  [CrossRef] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tuchinda, P., Munyoo, B., Pohmakotr, M., Thinapong, P., Sophasan, S., Santisuk, T. & Reutrakul, V. (2006). J. Nat. Prod. 69, 1728-1733.  [CrossRef] [PubMed] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o2274  [ doi:10.1107/S1600536812028334 ]

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