4′,5-Dihy­droxy-7-meth­oxy­flavanone dihydrate

Brito, I.; Bórquez, J.; Simirgiotis, M.; Cárdenas, A.; López-Rodríguez, M.

doi:10.1107/S1600536811051221

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 (C-C) = 0.007 Å
R = 0.075
wR = 0.180
Data-to-parameter ratio = 9.0
Details

4',5-Dihydroxy-7-methoxyflavanone dihydrate

Iván Brito,^a ^* Jorge Bórquez,^a Mario Simirgiotis,^a Alejandro Cárdenas ^b and Matías López-Rodríguez ^c

^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-HO 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). 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); Atkinson & Blakeman (1982). For its biological properties, see: Plowright et al. (1996); Atkinson & Blakeman (1982), Saito et al. (2008). For its spectroscopic properties, see: Agrawal (1989); Ogawa et al. (2007). For the structure of the unsolvated compound, see: Shoja (1990). For similar compounds, see: Modak et al. (2009). For graph-set notation, see: Bernstein et al. (1995). For puckering parameters, see: Cremer & Pople (1975). For molecular geometry calculations, see: Macrae et al. (2008).

Experimental

Crystal data

C₁₆H₁₄O₅·2H₂O
M_r = 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 radiation
= 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(I)
R_int = 0.068

Refinement

R[F² > 2(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
_max = 0.38 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3O2	0.82	1.90	2.630 (5)	147
O5-H5O7	0.76 (9)	1.99 (9)	2.720 (7)	163 (7)
O6-H6AO2ⁱ	0.87 (9)	2.00 (8)	2.847 (6)	166 (7)
O6-H6BO3ⁱⁱ	0.81 (6)	2.11 (6)	2.915 (5)	174 (8)
O7-H7AO5ⁱ	0.85	2.27	3.055 (7)	153
O7-H7BO6ⁱⁱⁱ	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; cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and publCIF (Westrip, 2010).

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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
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.
Modak, B., Rojas, M. & Torres, R. (2009). Molecules, 14, 1980-1989.
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Plowright, R. A., Grayer, R. J., Gill, J. R., Rahman, M. L. & Harborne, J. B. (1996). Nematologica, 42, 564-578.
Saito, T., Abe, D. & Sekiya, K. (2008). Biochem. Biophys. Res. Commun. 372, 835-839.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shoja, M. (1990). Acta Cryst. C46, 1969-1971.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds