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Volume 69 
Part 9 
Pages o1456-o1457  
September 2013  

Received 26 July 2013
Accepted 30 July 2013
Online 21 August 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.052
wR = 0.145
Data-to-parameter ratio = 18.0
Details
Open access

Racemic 2'-hydroxy-4',4'-dimethylpyran-1,5-dihydroxyxanthone monohydrate

aFaculty of Traditional Thai Medicine, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand,bDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand,cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and dDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia
Correspondence e-mail: suchada.c@psu.ac.th

The title xanthone (systematic name: 3,6,11-trihydroxy-1,1-dimethyl-2,3-dihydrochromeno[2,3-f]chromen-7-one monohydrate), known as pruniflorone N, crystallized as a monohydrate, C18H16O6·H2O. The three ring systems of the xanthone skeleton are approximately coplanar, with an r.m.s. deviation of 0.0270 (1) Å from the plane through the 14 non-H atoms. The O atoms of the two hydroxy substituents on the benzene rings also lie close to this plane, with deviations of 0.019 (1) and 0.070 (1) Å. The 2'-hydroxy-4',4'-dimethylpyran ring is disordered over two positions with a 0.798 (3):0.202 (3) site-occupancy ratio. An intramolecular O-H...O hydrogen bond generates an S(6) ring motif. In the crystal, the xanthone and water molecules are linked into a three-dimensional network by O-H...O hydrogen bonds and weak C-H...O interactions. [pi]-[pi] interactions, with centroid-centroid distances of 3.5982 (7), 3.6081 (7) and 3.6456 (7) Å, are also observed.

Related literature

For details of hydrogen-bond motifs, 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 ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For background to xanthones and their biological activity, see: Boonnak, Karalai et al. (2010[Boonnak, N., Karalai, C., Chantrapromma, S., Ponglimanont, C., Kanjana-Opas, A., Chantrapromma, K. & Kato, S. (2010). Chem. Pharm. Bull. 58, 386-389.]); Boonnak, Khamthip et al. (2010[Boonnak, N., Khamthip, A., Karalai, C., Chantrapromma, S., Ponglimanont, C., Kanjana-Opas, A., Tewtrakul, S., Chantrapromma, K., Fun, H.-K. & Kato, S. (2010). Aust. J. Chem.. 63, 1550-1556.]); Gopalakrishnan et al. (1997[Gopalakrishnan, G., Banumathi, B. & Suresh, G. (1997). J. Nat. Prod. 60, 519-524.]); Ho et al. (2002[Ho, C. K., Huang, Y. L. & Chen, C. C. (2002). Planta Med. 68, 975-979.]); Obolskiy et al. (2009[Obolskiy, D., Pischel, I., Siriwatanametanon, N. & Heinrich, M. (2009). Phytother. Res. 23, 1047-1065.]). For related structures, see: Boonnak et al. (2006[Boonnak, N., Chantrapromma, S. & Fun, H.-K. (2006). Acta Cryst. E62, o2034-o2036.]); Boonnak, Chantrapromma et al. (2010[Boonnak, N., Chantrapromma, S., Fun, H.-K. & Karalai, C. (2010). Acta Cryst. E66, o817-o818.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C18H16O6·H2O

  • Mr = 346.20

  • Orthorhombic, P b c a

  • a = 9.8965 (2) Å

  • b = 15.2329 (3) Å

  • c = 20.1122 (4) Å

  • V = 3031.96 (10) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 100 K

  • 0.65 × 0.21 × 0.13 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.927, Tmax = 0.985

  • 40070 measured reflections

  • 4949 independent reflections

  • 4378 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.145

  • S = 1.04

  • 4949 reflections

  • 275 parameters

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

  • [Delta][rho]max = 0.71 e Å-3

  • [Delta][rho]min = -0.97 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H1O4...O3 0.92 (3) 1.67 (3) 2.5337 (14) 156 (3)
O1-H1O1...O1Wi 0.86 (2) 1.81 (2) 2.6599 (16) 172.5 (19)
O1W-H2W1...O4ii 0.77 (2) 2.13 (2) 2.8756 (16) 166 (2)
O1W-H1W1...O6Aiii 0.88 (3) 1.93 (3) 2.8078 (17) 175 (3)
O6A-H6A...O1iii 0.82 (3) 2.10 (3) 2.8838 (16) 160 (3)
C18A-H18A...O6A 0.96 2.44 3.078 (2) 124
C18A-H18C...O4iv 0.96 2.60 3.530 (2) 164
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (ii) [-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (iv) [x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) 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: SJ5348 ).


Acknowledgements

The authors thank Prince of Songkla University for generous support. The authors extend their appreciation to the Deanship of Scientific Research at the King Saud University and the Universiti Sains Malaysia for the APEX DE2012 grant No. 1002/PFIZIK/910323.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Boonnak, N., Chantrapromma, S. & Fun, H.-K. (2006). Acta Cryst. E62, o2034-o2036.  [CSD] [CrossRef] [ChemPort] [details]
Boonnak, N., Chantrapromma, S., Fun, H.-K. & Karalai, C. (2010). Acta Cryst. E66, o817-o818.  [CrossRef] [ChemPort] [details]
Boonnak, N., Karalai, C., Chantrapromma, S., Ponglimanont, C., Kanjana-Opas, A., Chantrapromma, K. & Kato, S. (2010). Chem. Pharm. Bull. 58, 386-389.  [CrossRef] [ChemPort] [PubMed]
Boonnak, N., Khamthip, A., Karalai, C., Chantrapromma, S., Ponglimanont, C., Kanjana-Opas, A., Tewtrakul, S., Chantrapromma, K., Fun, H.-K. & Kato, S. (2010). Aust. J. Chem.. 63, 1550-1556.  [ISI] [CSD] [CrossRef] [ChemPort]
Bruker (2009). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Gopalakrishnan, G., Banumathi, B. & Suresh, G. (1997). J. Nat. Prod. 60, 519-524.  [CrossRef] [ChemPort] [PubMed] [ISI]
Ho, C. K., Huang, Y. L. & Chen, C. C. (2002). Planta Med. 68, 975-979.  [ISI] [CrossRef] [PubMed] [ChemPort]
Obolskiy, D., Pischel, I., Siriwatanametanon, N. & Heinrich, M. (2009). Phytother. Res. 23, 1047-1065.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1456-o1457   [ doi:10.1107/S1600536813021223 ]

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