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Volume 69 
Part 1 
Pages o14-o15  
January 2013  

Received 14 November 2012
Accepted 29 November 2012
Online 5 December 2012

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Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.125
Data-to-parameter ratio = 10.2
Details
Open access

Cytosinium orotate dihydrate

Gustavo Portalonea*

aChemistry Department, "Sapienza" University of Rome, P.le A. Moro, 5, I-00185 Rome, Italy
Correspondence e-mail: g.portalone@caspur.it

The title compound, C4H6N3O+·C5H3N2O4-·2H2O or Cyt+·Or-·2H2O, was synthesized by a reaction between cytosine (4-amino-2-hydroxypyrimidine, Cyt) and orotic acid (2,4-dihydroxy-6-carboxypyrimidine, Or) in aqueous solution. The two ions are joined by two N+-H...O- (±)-(CAHB) hydrogen bonds, forming a dimer with graph-set motif R22(8). In the crystal, the ion pairs of the asymmetric unit are joined by four N-H...O interactions to adjacent dimers, forming hydrogen-bonded rings with R22(8) graph-set motif in a two-dimensional network. The formation of the three-dimensional array is facilitated by water molecules, which act as bridges between structural sub-units linked in R32(8) and R32(7) hydrogen-bonded rings. The orotate anion is essentially planar, as the dihedral angle between the planes defined by the carboxylate group and the uracil fragment is 4.0 (4)°.

Related literature

For the supramolecular association in proton-transfer adducts containing molecules of biological interest, see: Portalone & Colapietro (2007[Portalone, G. & Colapietro, M. (2007). J. Chem. Crystallogr. 37, 141-145.], 2009[Portalone, G. & Colapietro, M. (2009). J. Chem. Crystallogr. 39, 193-200.]); Portalone (2010[Portalone, G. (2010). Acta Cryst. C66, o295-o301.], 2011[Portalone, G. (2011). Chem. Centr. J. 5, 51.]); Portalone & Irrera (2011[Portalone, G. & Irrera, S. (2011). J. Mol. Struct. 991, 92-96.]). For the crystal structure of neutral cytosine, see: McClure & Craven (1973[McClure, R. J. & Craven, B. M. (1973). Acta Cryst. B29, 1234-1238.]). For the crystal structures of orotic acid and its salts, see: Lutz (2001[Lutz, M. (2001). Acta Cryst. E57, m103-m105.]); Portalone (2008[Portalone, G. (2008). Acta Cryst. E64, o656.]); Solbakk (1971[Solbakk, J. (1971). Acta Chem. Scand. 25, 3006-3018.]). For computation of ring patterns formed by hydrogen bonds in crystal structures, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C4H6N3O+·C5H3N2O4-·2H2O

  • Mr = 303.24

  • Monoclinic, P 21 /c

  • a = 5.1486 (2) Å

  • b = 15.1631 (6) Å

  • c = 16.4206 (7) Å

  • [beta] = 90.562 (3)°

  • V = 1281.87 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.14 mm-1

  • T = 298 K

  • 0.15 × 0.10 × 0.10 mm
Data collection

  • Oxford Diffraction Xcalibur S CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.980, Tmax = 0.987

  • 27833 measured reflections

  • 2328 independent reflections

  • 1954 reflections with I > 2[sigma](I)

  • Rint = 0.034
Refinement

  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.125

  • S = 1.13

  • 2328 reflections

  • 228 parameters

  • 4 restraints

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

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N7-H7...O1i 0.76 (2) 2.05 (2) 2.809 (2) 172 (2)
N10-H10A...O3 0.97 (3) 1.90 (3) 2.871 (2) 173 (2)
N10-H10B...O6W 0.87 (2) 2.05 (2) 2.876 (3) 158 (2)
N9-H9...O4 0.86 (3) 1.87 (3) 2.7299 (19) 176 (2)
N1-H1...O5ii 0.88 (2) 2.20 (2) 3.051 (2) 165.6 (17)
N3-H3...O1iii 0.93 (2) 1.93 (2) 2.8624 (18) 179.3 (19)
O6W-H61...O2ii 0.85 (2) 1.99 (2) 2.806 (2) 163 (4)
O6W-H62...O7Wiv 0.87 (2) 2.07 (3) 2.873 (4) 154 (4)
O7W-H71...O4 0.90 (2) 1.97 (2) 2.867 (2) 173 (4)
O7W-H72...O5 0.90 (2) 2.27 (3) 2.979 (2) 136 (3)
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) -x-2, -y, -z+1; (iv) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5024 ).

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Lutz, M. (2001). Acta Cryst. E57, m103-m105.  [CSD] [CrossRef] [details]
McClure, R. J. & Craven, B. M. (1973). Acta Cryst. B29, 1234-1238.  [CrossRef] [ChemPort] [details] [ISI]
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Portalone, G. (2008). Acta Cryst. E64, o656.  [CSD] [CrossRef] [details]
Portalone, G. (2010). Acta Cryst. C66, o295-o301.  [CSD] [CrossRef] [details]
Portalone, G. (2011). Chem. Centr. J. 5, 51.  [CSD] [CrossRef]
Portalone, G. & Colapietro, M. (2007). J. Chem. Crystallogr. 37, 141-145.  [ISI] [CSD] [CrossRef] [ChemPort]
Portalone, G. & Colapietro, M. (2009). J. Chem. Crystallogr. 39, 193-200.  [ISI] [CSD] [CrossRef] [ChemPort]
Portalone, G. & Irrera, S. (2011). J. Mol. Struct. 991, 92-96.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Solbakk, J. (1971). Acta Chem. Scand. 25, 3006-3018.  [CrossRef] [ChemPort]

Acta Cryst (2013). E69, o14-o15   [ doi:10.1107/S1600536812049057 ]

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