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Volume 66 
Part 3 
Page o620  
March 2010  

Received 8 February 2010
Accepted 9 February 2010
Online 13 February 2010

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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.038
wR = 0.102
Data-to-parameter ratio = 8.8
Details
Open access

Meranzin hydrate from Muraya paniculata

Euis Julaeha,a Unang Supratman,a Mat Ropi Mukhtar,b Khalijah Awangb and Seik Weng Ngb*

aDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Padjadjaran University, Jatinangor 45363, West Java, Indonesia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

The coumarin ring system in the title compound, C15H18O5 [IUPAC name: 8-(2,3-dihydroxy-3-methylbutyl)-7-methoxy-2H-1-benzopyran-2-one], isolated from Muraya paniculata, is planar (r.m.s. deviation 0.017 Å). In the crystal, the two hydroxy groups are involved in O-H...O hydrogen bonding with adjacent molecules, forming a sheet structure.

Related literature

For the asymmetric synthesis and absolute configuration of meranzin hydrate, see: Grundon & McColl (1975[Grundon, M. F. & McColl, I. S. (1975). Phytochemistry, 14, 143-150.]).

[Scheme 1]

Experimental

Crystal data

  • C15H18O5

  • Mr = 278.29

  • Monoclinic, P 21

  • a = 5.8061 (7) Å

  • b = 10.5146 (13) Å

  • c = 11.4477 (14) Å

  • [beta] = 91.547 (2)°

  • V = 698.61 (15) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.35 × 0.15 × 0.15 mm
Data collection

  • Bruker SMART APEX diffractometer

  • 6694 measured reflections

  • 1699 independent reflections

  • 1338 reflections with I > 2[sigma](I)

  • Rint = 0.040
Refinement

  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.102

  • S = 1.00

  • 1699 reflections

  • 192 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.12 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H4...O2i 0.84 (1) 2.01 (1) 2.842 (3) 169 (5)
O5-H5...O2ii 0.85 (1) 2.12 (2) 2.936 (3) 163 (4)
Symmetry codes: (i) x-1, y, z; (ii) [-x+3, y-{\script{1\over 2}}, -z+2].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: publCIF (Westrip, 2010[Westrip, S. P. (2010). publCIF. In preparation.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5194 ).

Acknowledgements

This work was supported by the Directorate General of Higher Education, Ministry of National Education, Indonesia (BPPS-Doctoral Program), the I-MHERE Project of Padjadjaran University, the Science Fund of Malaysia (12-02-03-2063) and the University of Malaya.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Grundon, M. F. & McColl, I. S. (1975). Phytochemistry, 14, 143-150.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). publCIF. In preparation.

Acta Cryst (2010). E66, o620  [ doi:10.1107/S1600536810005386 ]

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