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Volume 68 
Part 1 
Pages o32-o33  
January 2012  

Received 11 October 2011
Accepted 28 November 2011
Online 7 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.007 Å
R = 0.075
wR = 0.180
Data-to-parameter ratio = 9.0
Details
Open access

4',5-Dihydroxy-7-methoxyflavanone dihydrate

aDepartamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta, Casilla 170, Antofagasta, Chile,bDepartamento de Física, Facultad de Ciencias Básicas, Universidad de Antofagasta, Casilla 170, Antofagasta, Chile, and cInstituto de Bio-Orgánica 'Antonio González', Universidad de La Laguna, Astrofísico Francisco Sánchez N°2, La Laguna, Tenerife, Spain
Correspondence e-mail: ivanbritob@yahoo.com

The title compound, C16H14O5·2H2O [systematic name: 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychroman-4-one dihydrate], is a natural phytoalexin flavone isolated from the native chilean species Heliotropium taltalense and crystallizes with an organic molecule and two water molecules in the asymmetric unit. The 5-hydroxy group forms a strong intramolecular hydrogen bond with the carbonyl group, resulting in a six-membered ring. In the crystal, the components are linked by O-H...O hydrogen bonds, forming a three-dimensional network. The 4-hydroxyphenyl benzene ring is bonded equatorially to the pyrone ring, which adopts a slightly distorted sofa conformation. The title compound is the hydrated form of a previously reported structure [Shoja (1990[Shoja, M. (1990). Acta Cryst. C46, 1969-1971.]). Acta Cryst. C46, 1969-1971]. There are only slight variations in the molecular geometry between the two compounds.

Related literature

For the first study of the title compound, see: Narasimhachari & Seshadri (1949[Narasimhachari, N. & Seshadri, T. R. (1949). Proc. Indian Acad. Sci. A. 29, 265-268.]); Atkinson & Blakeman (1982[Atkinson, P. & Blakeman, J. P. (1982). New Phytol. 92, 63-74.]). For its biological properties, see: Plowright et al. (1996[Plowright, R. A., Grayer, R. J., Gill, J. R., Rahman, M. L. & Harborne, J. B. (1996). Nematologica, 42, 564-578.]); Atkinson & Blakeman (1982[Atkinson, P. & Blakeman, J. P. (1982). New Phytol. 92, 63-74.]), Saito et al. (2008[Saito, T., Abe, D. & Sekiya, K. (2008). Biochem. Biophys. Res. Commun. 372, 835-839.]). For its spectroscopic properties, see: Agrawal (1989[Agrawal, P. K. (1989). In Carbon-13 NMR of Flavonoids. Amsterdam: Elsevier.]); Ogawa et al. (2007[Ogawa, Y., Oku, H., Iwaoka, E., Iinuma, M. & Ishiguro, K. (2007). Chem. Pharm. Bull. 55, 675-678.]). For the structure of the unsolvated compound, see: Shoja (1990[Shoja, M. (1990). Acta Cryst. C46, 1969-1971.]). For similar compounds, see: Modak et al. (2009[Modak, B., Rojas, M. & Torres, R. (2009). Molecules, 14, 1980-1989.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For molecular geometry calculations, see: Macrae et al. (2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]).

[Scheme 1]

Experimental

Crystal data
  • C16H14O5·2H2O

  • Mr = 322.30

  • Orthorhombic, P 21 21 21

  • a = 5.0869 (10) Å

  • b = 9.4622 (19) Å

  • c = 32.318 (7) Å

  • V = 1555.6 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.20 × 0.15 × 0.03 mm

Data collection
  • Nonius KappaCCD area-detector diffractometer

  • 9743 measured reflections

  • 2021 independent reflections

  • 1623 reflections with I > 2[sigma](I)

  • Rint = 0.068

Refinement
  • R[F2 > 2[sigma](F2)] = 0.075

  • wR(F2) = 0.180

  • S = 1.17

  • 2021 reflections

  • 224 parameters

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

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3...O2 0.82 1.90 2.630 (5) 147
O5-H5...O7 0.76 (9) 1.99 (9) 2.720 (7) 163 (7)
O6-H6A...O2i 0.87 (9) 2.00 (8) 2.847 (6) 166 (7)
O6-H6B...O3ii 0.81 (6) 2.11 (6) 2.915 (5) 174 (8)
O7-H7A...O5i 0.85 2.27 3.055 (7) 153
O7-H7B...O6iii 0.85 1.94 2.763 (6) 163
Symmetry codes: (i) x+1, y, z; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1].

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]; cell refinement: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO-SMN; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) 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: KJ2193 ).


Acknowledgements

IB thanks the Spanish Research Council (CSIC) for providing us with a free-of-charge licence for the CSD system. The authors acknowdledge funds from FONDECYT (1110068) and U. Antofagasta (CODEI N° 1383).

References

Agrawal, P. K. (1989). In Carbon-13 NMR of Flavonoids. Amsterdam: Elsevier.
Atkinson, P. & Blakeman, J. P. (1982). New Phytol. 92, 63-74.  [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Modak, B., Rojas, M. & Torres, R. (2009). Molecules, 14, 1980-1989.  [CrossRef] [PubMed] [ChemPort]
Narasimhachari, N. & Seshadri, T. R. (1949). Proc. Indian Acad. Sci. A. 29, 265-268.
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Ogawa, Y., Oku, H., Iwaoka, E., Iinuma, M. & Ishiguro, K. (2007). Chem. Pharm. Bull. 55, 675-678.  [CrossRef] [PubMed] [ChemPort]
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Plowright, R. A., Grayer, R. J., Gill, J. R., Rahman, M. L. & Harborne, J. B. (1996). Nematologica, 42, 564-578.  [CrossRef]
Saito, T., Abe, D. & Sekiya, K. (2008). Biochem. Biophys. Res. Commun. 372, 835-839.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shoja, M. (1990). Acta Cryst. C46, 1969-1971.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o32-o33   [ doi:10.1107/S1600536811051221 ]

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