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Volume 68 
Part 1 
Pages o235-o236  
January 2012  

Received 16 December 2011
Accepted 19 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.020
wR = 0.050
Data-to-parameter ratio = 12.2
Details
Open access

Tetragonal polymorph of 5,5-dichlorobarbituric acid

aInstitute of Pharmacy, University of Innsbruck, Innrain 52c, 6020 Innsbruck, Austria
Correspondence e-mail: thomas.gelbrich@uibk.ac.at

The tetragonal polymorph of 5,5-dichlorobarbituric acid (m.p. 478 K), C4H2Cl2N2O3, forms an N-H...O hydrogen-bonded tape structure along [001]. Two tapes related by a twofold rotation axis are associated via Cl...O contacts [3.201 (1) Å], and four such chain pairs are arranged around a fourfold roto-inversion axis. The crystal structures of the monoclinic and orthorhombic polymorphs have been reported previously [Gelbrich et al. (2011[Gelbrich, T., Rossi, D., Häfele, C. A. & Griesser, U. J. (2011). CrystEngComm, 13, 5502-5509.]). CrystEngComm, 13, 5502-5509].

Related literature

The polymorphic nature of 5,5-dichlorobarbituric acid was mentioned in Groth's compendium on the chemical crystallography of organic compounds, published more than a hundred years ago (Groth, 1910[Groth, P. (1910). Chemische Krystallographie. Dritter Teil. Aliphatische und hydroaromatische Kohlenstoffverbindungen, p. 579. Leipzig: Verlag von Wilhelm Engelmann.]). For the monoclinic and orthorhombic polymorphs, see: Gelbrich et al. (2011[Gelbrich, T., Rossi, D., Häfele, C. A. & Griesser, U. J. (2011). CrystEngComm, 13, 5502-5509.]). For related structures, see: Gartland & Craven (1971[Gartland, G. L. & Craven, B. M. (1971). Acta Cryst. B27, 1909-1916.]); Gelbrich et al. (2007[Gelbrich, T., Zencirci, N. & Griesser, U. J. (2007). Acta Cryst. C63, o751-o753.], 2010[Gelbrich, T., Zencirci, N. & Griesser, U. J. (2010). Acta Cryst. C66, o55-o58.], 2010a[Gelbrich, T., Rossi, D. & Griesser, U. J. (2010a). Acta Cryst. E66, o1219.],b[Gelbrich, T., Rossi, D. & Griesser, U. J. (2010b). Acta Cryst. E66, o2688.]); Nichol & Clegg (2007[Nichol, G. S. & Clegg, W. (2007). Acta Cryst. E63, o1632-o1634.]); Zencirci et al. (2009[Zencirci, N., Gelbrich, T., Kahlenberg, V. & Griesser, U. J. (2009). Cryst. Growth Des. 9, 3444-3456.], 2010[Zencirci, N., Gelbrich, T., Apperley, D. C., Harris, R. K., Kahlenberg, V. & Griesser, U. J. (2010). Cryst. Growth Des. 10, 302-313.]); DesMarteau et al. (1994[DesMarteau, D. D., Pennington, W. T. & Resnati, G. (1994). Acta Cryst. C50, 1305-1308.]). For a description of the synthesis, see: Ziegler et al. (1962[Ziegler, E., Salvador, R. & Kappe, T. (1962). Monatsh. Chem. 93, 1376-1382.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555-1573.]); Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data
  • C4H2Cl2N2O3

  • Mr = 196.98

  • Tetragonal, [P \overline 42_1 c ]

  • a = 13.8883 (3) Å

  • c = 6.9126 (2) Å

  • V = 1333.34 (6) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.92 mm-1

  • T = 173 K

  • 0.20 × 0.05 × 0.05 mm

Data collection
  • Oxford Diffraction Xcalibur Ruby Gemini ultra diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2003[Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.837, Tmax = 0.955

  • 11025 measured reflections

  • 1310 independent reflections

  • 1242 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.020

  • wR(F2) = 0.050

  • S = 1.07

  • 1310 reflections

  • 107 parameters

  • 2 restraints

  • All H-atom parameters refined

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 541 Friedel pairs

  • Flack parameter: -0.08 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3...O6i 0.87 (1) 2.07 (1) 2.923 (2) 167 (2)
N1-H1...O2ii 0.86 (1) 2.05 (1) 2.881 (2) 165 (2)
Symmetry codes: (i) x, y, z-1; (ii) [y+{\script{1\over 2}}, x-{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2003[Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2003[Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) 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: 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: SU2351 ).


Acknowledgements

TG gratefully acknowledges financial support from the Lize Meitner Program of the Austrian Science Fund (FWF, project M 1135-N17). We thank Clemens Häfele for providing a sample of 5,5-dichlorobarbituric acid and Professor Volker Kahlenberg for access to the X-ray instrument used in this study.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
DesMarteau, D. D., Pennington, W. T. & Resnati, G. (1994). Acta Cryst. C50, 1305-1308.  [CrossRef] [details]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Gartland, G. L. & Craven, B. M. (1971). Acta Cryst. B27, 1909-1916.  [CrossRef] [ChemPort] [details] [ISI]
Gelbrich, T., Rossi, D. & Griesser, U. J. (2010a). Acta Cryst. E66, o1219.  [CSD] [CrossRef] [details]
Gelbrich, T., Rossi, D. & Griesser, U. J. (2010b). Acta Cryst. E66, o2688.  [CSD] [CrossRef] [details]
Gelbrich, T., Rossi, D., Häfele, C. A. & Griesser, U. J. (2011). CrystEngComm, 13, 5502-5509.  [ISI] [CSD] [CrossRef] [ChemPort]
Gelbrich, T., Zencirci, N. & Griesser, U. J. (2007). Acta Cryst. C63, o751-o753.  [CSD] [CrossRef] [details]
Gelbrich, T., Zencirci, N. & Griesser, U. J. (2010). Acta Cryst. C66, o55-o58.  [CSD] [CrossRef] [details]
Groth, P. (1910). Chemische Krystallographie. Dritter Teil. Aliphatische und hydroaromatische Kohlenstoffverbindungen, p. 579. Leipzig: Verlag von Wilhelm Engelmann.
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]
Nichol, G. S. & Clegg, W. (2007). Acta Cryst. E63, o1632-o1634.  [CSD] [CrossRef] [details]
Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zencirci, N., Gelbrich, T., Apperley, D. C., Harris, R. K., Kahlenberg, V. & Griesser, U. J. (2010). Cryst. Growth Des. 10, 302-313.  [CSD] [CrossRef] [ChemPort]
Zencirci, N., Gelbrich, T., Kahlenberg, V. & Griesser, U. J. (2009). Cryst. Growth Des. 9, 3444-3456.  [CSD] [CrossRef] [ChemPort]
Ziegler, E., Salvador, R. & Kappe, T. (1962). Monatsh. Chem. 93, 1376-1382.  [ChemPort]


Acta Cryst (2012). E68, o235-o236   [ doi:10.1107/S1600536811054626 ]

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