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Volume 68 
Part 11 
Pages o3233-o3234  
November 2012  

Received 28 September 2012
Accepted 21 October 2012
Online 27 October 2012

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.104
Data-to-parameter ratio = 21.4
Details
Open access

1,3-Dicyclohexylimidazolidine-2,4,5-trione: a second polymorph

aDepartment of Chemistry, University of Aveiro, QOPNA, 3810-193 Aveiro, Portugal, and bDepartment of Chemistry, University of Aveiro, CICECO, 3810-193 Aveiro, Portugal
Correspondence e-mail: artur.silva@ua.pt, filipe.paz@ua.pt

The title compound, C15H22N2O3, was obtained as a by-product of oxidative cleavage of 1,3-dicyclohexyl-(3-oxo-2,3-dihydrobenzofuran-2-yl)imidazolidine-2,4-dione. Herein, we report the crystal structure of a second polymorph, which was obtained by crystallization from an ethanol solution at 253 K, instead of slow evaporation of the same solvent at room temperature. While the first polymorph [Talhi et al. (2011). Acta Cryst. E67, o3243] crystallized in the non-centrosymmetric space group P212121, this second polymorph crystallizes in the centrosymmetric space group P21/n. Compared to the first polymorph, in the crystal no C=O...C=O interactions were found (C...O intermolecular distance longer than 3.15 Å) and instead, close packing of individual molecular units is mediated by C-H...[pi] and weak C-H...O interactions.

Related literature

For the structure of the orthorhombic polymorph and further background information to the study, see: Talhi et al. (2011[Talhi, O., Fernandes, J. A., Pinto, D. C. G. A., Silva, A. M. S. & Almeida Paz, F. A. (2011). Acta Cryst. E67, o3243.]). For general background on crystallographic studies by our research group of related compounds having biological activity, see: Fernandes et al. (2011[Fernandes, J. A., Almeida Paz, F. A., Marques, J., Marques, M. P. M. & Braga, S. S. (2011). Acta Cryst. C67, o57-o59.]); Loughzail et al. (2011[Loughzail, M., Fernandes, J. A., Baouid, A., Essaber, M., Cavaleiro, J. A. S. & Almeida Paz, F. A. (2011). Acta Cryst. E67, o2075-o2076.]). For determination of the melting point, see: Ulrichan & Sayigh (1965[Ulrichan, H. & Sayigh, D. A. A. R. (1965). J. Org. Chem. 30, 2781-2783.]).

[Scheme 1]

Experimental

Crystal data
  • C15H22N2O3

  • Mr = 278.35

  • Monoclinic, P 21 /n

  • a = 5.1980 (2) Å

  • b = 21.7123 (10) Å

  • c = 13.0244 (6) Å

  • [beta] = 100.163 (2)°

  • V = 1446.88 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 150 K

  • 0.13 × 0.06 × 0.06 mm

Data collection
  • Bruker X8 Kappa CCD APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1998[Sheldrick, G. M. (1998). SADABS. University of Göttingen, Germany.]) Tmin = 0.989, Tmax = 0.995

  • 38115 measured reflections

  • 3876 independent reflections

  • 2999 reflections with I > 2[sigma](I)

  • Rint = 0.049

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

  • wR(F2) = 0.104

  • S = 1.04

  • 3876 reflections

  • 181 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Short intermolecular interactions (Å, °)

Cg is the centroid of the N1/N2/C1-C3 ring.

D-H...A D-H H...A D...A D-H...A
C7-H7B...Cgi 0.99 2.78 3.5511 (14) 135
C11-H11B...O2ii 0.99 2.51 3.2065 (18) 127
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2005[Bruker (2005). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus (Bruker, 2005[Bruker (2005). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 2009[Brandenburg, K. (2009). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NK2188 ).


Acknowledgements

The authors gratefully acknowledge the Fundação para a Ciência e a Tecnologia (FCT, MEC, Portugal), the European Union, QREN, FEDER, COMPETE for financial support by the strategic projects PEst-C/CTM/LA0011/2011 (to CICECO) and PEst-C/QUI/UI0062/2011 (to QOPNA), the R&D project PTDC/QUI-QUI/098098/2008 (FCOMP-01-0124-FEDER-010785), as well as the post-doctoral research grant SFRH/BPD/63736/2009 (to JAF). We further wish to thank the FCT for specific funding towards the purchase of the single-crystal X-ray diffractometer. We also thank the European Community's Seventh Framework Programme (FP7/2007-20139 under grant agreement No. 215009).

References

Brandenburg, K. (2009). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2005). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2006). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Fernandes, J. A., Almeida Paz, F. A., Marques, J., Marques, M. P. M. & Braga, S. S. (2011). Acta Cryst. C67, o57-o59.  [CSD] [CrossRef] [details]
Loughzail, M., Fernandes, J. A., Baouid, A., Essaber, M., Cavaleiro, J. A. S. & Almeida Paz, F. A. (2011). Acta Cryst. E67, o2075-o2076.  [CrossRef] [details]
Sheldrick, G. M. (1998). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Talhi, O., Fernandes, J. A., Pinto, D. C. G. A., Silva, A. M. S. & Almeida Paz, F. A. (2011). Acta Cryst. E67, o3243.  [CSD] [CrossRef] [details]
Ulrichan, H. & Sayigh, D. A. A. R. (1965). J. Org. Chem. 30, 2781-2783.


Acta Cryst (2012). E68, o3233-o3234   [ doi:10.1107/S1600536812043619 ]

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