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Volume 69 
Part 11 
Pages o1707-o1708  
November 2013  

Received 18 October 2013
Accepted 21 October 2013
Online 26 October 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.115
Data-to-parameter ratio = 12.2
Details
Open access

4-Hy­droxy-5-(2-meth­oxy­phen­oxy)-2,2'-bipyrimidin-6(5H)-one dihydrate

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
Correspondence e-mail: jjasinski@keene.edu

The title compound, C15H12N4O4·2H2O, crystallizes with two independent water mol­ecules in the asymmetric unit. The dihedral angles between the mean planes of the benzene and pyrimidine rings and that of the pyrimidin-4-one ring are 85.1 (9) and 82.1 (1)°, respectively. The mean plane of the pyrimidine ring is twisted by 12.8 (8)° from that of the pyrimidin-4-one ring. The dihedral angles between the benzene ring and the mean planes of the pyrimidine and pyrimidin-4-one rings are 85.1 (9) and 82.1 (1)°, respectively.In the crystal, N-H...O, O-H...N and O-H...O hydrogen bonds involving both water mol­ecules are present; these link the mol­ecules into a two-dimensional network parallel to (010). In addition, weak C-H...[pi] and [pi]-[pi] [centroid-centroid distance = 3.6183 (8) Å] inter­actions occur.

Related literature

For substituted pyrimidine-2,4-diones as good reversible inhibitors of thymidine phospho­rylase, see: Baker & Rzeszotarki (1967[Baker, B. R. & Rzeszotarki, W. (1967). J. Med. Chem. 10, 1109-1113.]). For the use of 2,2'-bi­pyrimidine as a ligand in inorganic and organometallic chemistry, see: Hunziker & Ludi (1977[Hunziker, M. & Ludi, A. (1977). J. Am. Chem. Soc. 99, 7370-7371]); Fabrice et al. (2008[Fabrice, P., Patr, H., Kamal, B. & Cyri, T. (2008). Inorg. Chim. Acta, 361, 373-379.]). For related structures, see: El-Brollosy et al. (2012[El-Brollosy, N. R., El-Emam, A. A., Al-Deeb, O. A. & Ng, S. W. (2012). Acta Cryst. E68, o316.]); Fun et al. (2009[Fun, H.-K., Goh, J. H., Reddy, B. P., Vijayakumar, V. & Sarveswari, S. (2009). Acta Cryst. E65, o2655-o2656.]); Kaur et al. (2013[Kaur, M., Jasinski, J. P., Keeley, A. C., Yathirajan, H. S., Betz, R., Gerber, T. & Butcher, R. J. (2013). Acta Cryst. E69, o12-o13.]); Ren et al. (2011[Ren, T., Zhang, Z., Zhong, C., Yang, Z. & Shi, Z. (2011). Acta Cryst. E67, o1334.]); Trilleras et al. (2009[Trilleras, J., Quiroga, J., Cobo, J., Hursthouse, M. B. & Glidewell, C. (2009). Acta Cryst. C65, o134-o139.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12N4O4·2H2O

  • Mr = 348.32

  • Monoclinic, P 21 /c

  • a = 9.5817 (3) Å

  • b = 13.9439 (3) Å

  • c = 12.4804 (4) Å

  • [beta] = 109.832 (3)°

  • V = 1568.55 (8) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.99 mm-1

  • T = 173 K

  • 0.45 × 0.32 × 0.24 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.876, Tmax = 1.000

  • 9840 measured reflections

  • 3070 independent reflections

  • 2789 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.115

  • S = 1.03

  • 3070 reflections

  • 252 parameters

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

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C9-C14 ring.

D-H...A D-H H...A D...A D-H...A
O3-H3...O2Wi 0.91 (3) 1.67 (3) 2.5651 (15) 172 (2)
N4-H4...O1ii 0.88 (2) 2.08 (2) 2.9313 (15) 163.6 (18)
O1W-H1WA...O4iii 0.87 (2) 2.05 (2) 2.8917 (16) 163 (2)
O1W-H1WB...N2iv 0.89 (3) 2.01 (3) 2.8823 (16) 167 (2)
O2W-H2WA...O4 0.86 (2) 1.93 (3) 2.7803 (15) 172 (2)
O2W-H2WB...O1Wv 0.91 (3) 1.80 (3) 2.7050 (17) 173 (2)
C4-H4A...Cg3vi 0.95 2.82 3.4083 (16) 121
Symmetry codes: (i) [x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) -x+1, -y+1, -z+1; (iv) -x+2, -y+1, -z+1; (v) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (vi) [x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6940 ).


Acknowledgements

TSY thanks the University of Mysore for research facilities and is also grateful to the Principal, Maharani's Science College for Women, Mysore, for giving permission to undertake research. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Baker, B. R. & Rzeszotarki, W. (1967). J. Med. Chem. 10, 1109-1113.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
El-Brollosy, N. R., El-Emam, A. A., Al-Deeb, O. A. & Ng, S. W. (2012). Acta Cryst. E68, o316.  [CSD] [CrossRef] [IUCr Journals]
Fabrice, P., Patr, H., Kamal, B. & Cyri, T. (2008). Inorg. Chim. Acta, 361, 373-379.
Fun, H.-K., Goh, J. H., Reddy, B. P., Vijayakumar, V. & Sarveswari, S. (2009). Acta Cryst. E65, o2655-o2656.  [CrossRef] [ChemPort] [IUCr Journals]
Hunziker, M. & Ludi, A. (1977). J. Am. Chem. Soc. 99, 7370-7371  [CrossRef] [ChemPort] [Web of Science]
Kaur, M., Jasinski, J. P., Keeley, A. C., Yathirajan, H. S., Betz, R., Gerber, T. & Butcher, R. J. (2013). Acta Cryst. E69, o12-o13.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Ren, T., Zhang, Z., Zhong, C., Yang, Z. & Shi, Z. (2011). Acta Cryst. E67, o1334.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Trilleras, J., Quiroga, J., Cobo, J., Hursthouse, M. B. & Glidewell, C. (2009). Acta Cryst. C65, o134-o139.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1707-o1708   [ doi:10.1107/S1600536813028900 ]

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