Tetra­gonal polymorph of 5,5-dichloro­barbituric acid

Gelbrich, T.; Rossi, D.; Griesser, U.J.

doi:10.1107/S1600536811054626

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 (C-C) = 0.003 Å
R = 0.020
wR = 0.050
Data-to-parameter ratio = 12.2
Details

Tetragonal polymorph of 5,5-dichlorobarbituric acid

Thomas Gelbrich,^a ^* Denise Rossi ^a and Ulrich J. Griesser ^a

^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-HO hydrogen-bonded tape structure along [001]. Two tapes related by a twofold rotation axis are associated via ClO 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). 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). For the monoclinic and orthorhombic polymorphs, see: Gelbrich et al. (2011). For related structures, see: Gartland & Craven (1971); Gelbrich et al. (2007, 2010, 2010a,b); Nichol & Clegg (2007); Zencirci et al. (2009, 2010); DesMarteau et al. (1994). For a description of the synthesis, see: Ziegler et al. (1962). For hydrogen-bond motifs, see: Bernstein et al. (1995); Etter et al. (1990).

Experimental

Crystal data

C₄H₂Cl₂N₂O₃
M_r = 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 radiation
= 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 $[Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.837, T_max = 0.955
11025 measured reflections
1310 independent reflections
1242 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.020
wR(F²) = 0.050
S = 1.07
1310 reflections
107 parameters
2 restraints
All H-atom parameters refined
_max = 0.20 e Å^-3
_min = -0.16 e Å^-3
Absolute structure: Flack (1983), 541 Friedel pairs
Flack parameter: -0.08 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3O6ⁱ	0.87 (1)	2.07 (1)	2.923 (2)	167 (2)
N1-H1O2ⁱⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

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

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