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Volume 69 
Part 6 
Pages o863-o864  
June 2013  

Received 21 April 2013
Accepted 5 May 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
H completeness 96%
Disorder in solvent or counterion
R = 0.043
wR = 0.131
Data-to-parameter ratio = 9.4
Details
Open access

N,N-Diethyl-2-hydroxyethanaminium 5-(2,4-dinitrophenyl)barbiturate sesquihydrate

aPG and Research Department of Chemistry, Seethalakshmi Ramaswami College, Tiruchirappalli 620 002, Tamil Nadu, India
Correspondence e-mail: kalaivbalaj@yahoo.co.in

In the title hydrated molecular salt, C6H16NO+·C10H5N4O7-·1.5H2O [systematic name: N,N-diethyl-2-hydroxyethanaminium 5-(2,4-dinitrophenyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate sesquihydrate], the dihedral angle between the six-membered rings in the anion is 37.66 (11)°. The nitro groups ortho and para to the ring junction are rotated from their attached ring by 40.8 (3) and 23.5 (3)°, respectively. The ethanol group is disordered over two of the `arms' of the cation in a statistical ratio. In the crystal, [010] chains of anions occur, linked by N-H...O and O-H...O hydrogen bonds, which generate R22(8) loops. Further N-H...O and O-H...O hydrogen bonds link the components into a three-dimensional network. One of the water O atoms lies near an inversion centre and is 50% occupied.

Related literature

For related barbiturates, see: Kalaivani et al. (2008[Kalaivani, D., Malarvizhi, R. & Subbalakshmi, R. (2008). Med. Chem. Res. 17, 369-373.]); Kalaivani & Buvaneswari (2010[Kalaivani, D. & Buvaneswari, M. (2010). Recent Advances in Clinical Medicine, pp. 255-260. Cambridge, England: WSEAS Press UK.]); Buvaneswari & Kalaivani (2011[Buvaneswari, M. & Kalaivani, D. (2011). Acta Cryst. E67, o1433-o1434.]); Babykala & Kalaivani (2012[Babykala, R. & Kalaivani, D. (2012). Acta Cryst. E68, o541.]).

[Scheme 1]

Experimental

Crystal data
  • C6H16NO+·C10H5N4O7-·1.5H2O

  • Mr = 438.40

  • Monoclinic, P 21 /c

  • a = 9.6003 (5) Å

  • b = 11.6568 (6) Å

  • c = 18.1993 (9) Å

  • [beta] = 98.066 (3)°

  • V = 2016.51 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004)[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.] Tmin = 0.948, Tmax = 0.979

  • 16207 measured reflections

  • 3219 independent reflections

  • 2353 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.131

  • S = 1.09

  • 3219 reflections

  • 341 parameters

  • 49 restraints

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

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O8-H8...O9i 0.82 2.14 2.739 (10) 130
O9-H9...O11ii 0.82 2.11 2.841 (17) 148
N3-H3...O3iii 0.86 1.94 2.794 (2) 174
N4-H4A...O1iv 0.86 1.97 2.804 (3) 165
N5-H5A...O10ii 0.97 (4) 1.86 (4) 2.808 (4) 164 (3)
O10-H10B...O2 0.90 (2) 1.87 (3) 2.751 (3) 163 (5)
O10-H10A...O6iv 0.89 (2) 2.02 (2) 2.902 (4) 172 (6)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) [x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iv) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (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.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7074 ).


Acknowledgements

The authors are thankful to the SAIF, IIT Madras, for the data collection.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [ISI] [details]
Babykala, R. & Kalaivani, D. (2012). Acta Cryst. E68, o541.  [CSD] [CrossRef] [details]
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Buvaneswari, M. & Kalaivani, D. (2011). Acta Cryst. E67, o1433-o1434.  [CSD] [CrossRef] [ChemPort] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kalaivani, D. & Buvaneswari, M. (2010). Recent Advances in Clinical Medicine, pp. 255-260. Cambridge, England: WSEAS Press UK.
Kalaivani, D., Malarvizhi, R. & Subbalakshmi, R. (2008). Med. Chem. Res. 17, 369-373.  [ISI] [CrossRef] [ChemPort]
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]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o863-o864   [ doi:10.1107/S1600536813012257 ]

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