[Journal logo]

Volume 69 
Part 7 
Pages o1102-o1103  
July 2013  

Received 29 May 2013
Accepted 7 June 2013
Online 15 June 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.037
wR = 0.100
Data-to-parameter ratio = 20.1
Details
Open access

3-(4-Bromophenyl)-1-butyl-5-[1-(2-chloro-6-methylphenyl)-1H-tetrazol-5-yl]imidazolidine-2,4-dione

aDepartment of Chemistry and Biochemistry, University of Arizona, 1306 E University Blvd, Tucson, AZ 85721, USA, and bBIO5 Oro Valley, College of Pharmacy, University of Arizona, 1580 E. Hanley Blvd, Oro Valley, AZ 85737, USA
Correspondence e-mail: suer@email.arizona.edu

In the title molecule, C21H20BrClN6O2, the chloro-substituted benzene ring forms a dihedral angle of 77.84 (7)° with the tetrazole ring and the bromo-substituted ring forms a dihedral angle of 43.95 (6)° with the imidazole ring. The dihedral angle between the tetrazole and imidazole rings is 67.42 (8)°. The terminal methyl group of the butyl substituent is disordered over two sets of sites, with refined occupancies 0.67 (3) and 0.33 (3). In the crystal, there is a short Br...N contact of 3.183 (2) Å.

Related literature

For the biological activity of imidazoline-2,4-diones, see: Thenmozhiyal et al. (2004[Thenmozhiyal, J. C., Wong, P. T. H. & Chui, W. K. (2004). J. Med. Chem. 47, 1527-1535.]); Brazil & Pedley (1998[Brazil, C. W. & Pedley, T. A. (1998). Annu. Rev. Med. 49, 135-162.]); Luer (1998[Luer, M. S. (1998). Neurol. Res. 20, 178-182.]); Matzukura et al. (1992[Matzukura, M., Daiku, Y., Ueda, K., Tanaka, S., Igarashi, T. & Minami, N. (1992). Chem. Pharm. Bull. 40, 1823-1827.]); Knabe et al. (1997[Knabe, J., Baldauf, J. & Ahlhelm, A. (1997). Pharmazie, 52, 912-919.]); Somsák et al. (2001[Somsák, L., Kovács, L., Tóth, M., Ösz, E., Szilágyi, L., Györgydeak, Z., Dinya, Z., Docsa, T., Tóth, B. & Gergely, P. (2001). J. Med. Chem. 44, 2843-2848.]); Moloney et al. (2001[Moloney, G. P., Robertson, A. D., Martin, G. R., MacLennan, S., Mathews, N., Dosworth, S., Sang, P. Y., Knight, C. & Glen, R. (2001). J. Med. Chem. 44, 2843-2848.]); Moloney et al. (1999[Moloney, G. P., Martin, G. R., Mathews, N., Milne, A., Hobbs, H., Dosworth, S., Sang, P. Y., Knight, C., Maxwell, M. & Glen, R. (1999). J. Med. Chem. 42, 2504-2526.]); Sutherland & Hess (2000[Sutherland, J. C. & Hess, G. P. (2000). Nat. Prod. Rep. 17, 621-631.]). For information on 1-5-disubstituted tetrazoles. see: Al-Hourani et al. (2011[Al-Hourani, B. J., Sharma, S. K., Mane, J. Y., Tuszynski, J., Baracos, V., Kniess, T., Suresh, M., Pietzsch, J. & Wuest, F. (2011). Bioorg. Med. Chem. Lett. 21, 1823-1826.]); Brazil & Pedley (1998[Brazil, C. W. & Pedley, T. A. (1998). Annu. Rev. Med. 49, 135-162.]); Davulcu et al. (2009[Davulcu, A. H., McLeod, D. D., Li, L., Katipally, K., Littke, A., Doubleday, W., Xu, Z., McConlogue, C. W., Lai, C. J., Gleeson, M., Schwinden, M. & Parsons, R. L. Jr (2009). J. Org. Chem. 74, 4068-4072.]); Herr (2002[Herr, R. J. (2002). Bioorg. Med. Chem. 10, 3379-3393.]); Quan et al. (2003[Quan, M. L., Ellis, C. D., He, M. Y., Liauw, A. Y., Woerner, F. J., Alexander, R. S., Knabb, R. M., Lam, P. Y. S. & Luettgen, J. M. (2003). Bioorg. Med. Chem. Lett. 13, 369-373.]); Van Poecke et al. (2011[Van Poecke, S., Negri, A., Janssens, J., Solaroli, N., Karlsson, A., Gago, F., Balzarini, J. & Van Calenberg, S. (2011). Org. Biomol. Chem. 9, 892-901.]).

[Scheme 1]

Experimental

Crystal data
  • C21H20BrClN6O2

  • Mr = 503.79

  • Monoclinic, C 2/c

  • a = 27.9412 (9) Å

  • b = 8.8675 (3) Å

  • c = 19.6581 (6) Å

  • [beta] = 112.500 (1)°

  • V = 4499.9 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 1.98 mm-1

  • T = 100 K

  • 0.36 × 0.2 × 0.03 mm

Data collection
  • Bruker APEXII DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.613, Tmax = 0.746

  • 79112 measured reflections

  • 5647 independent reflections

  • 4475 reflections with I > 2[sigma](I)

  • Rint = 0.043

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.100

  • S = 1.03

  • 5647 reflections

  • 281 parameters

  • 12 restraints

  • H-atom parameters not refined

  • [Delta][rho]max = 1.34 e Å-3

  • [Delta][rho]min = -1.07 e Å-3

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); 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: LH5623 ).


Acknowledgements

This work was supported by NIH grants (RC2MH090878 and P41GM086190) to CH. The Bruker Kappa APEXII DUO diffractometer was purchased with funding from NSF grant CHE-0741837.

References

Al-Hourani, B. J., Sharma, S. K., Mane, J. Y., Tuszynski, J., Baracos, V., Kniess, T., Suresh, M., Pietzsch, J. & Wuest, F. (2011). Bioorg. Med. Chem. Lett. 21, 1823-1826.  [ChemPort] [PubMed]
Brazil, C. W. & Pedley, T. A. (1998). Annu. Rev. Med. 49, 135-162.  [Web of Science] [PubMed]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Davulcu, A. H., McLeod, D. D., Li, L., Katipally, K., Littke, A., Doubleday, W., Xu, Z., McConlogue, C. W., Lai, C. J., Gleeson, M., Schwinden, M. & Parsons, R. L. Jr (2009). J. Org. Chem. 74, 4068-4072.  [CrossRef] [PubMed] [ChemPort]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Herr, R. J. (2002). Bioorg. Med. Chem. 10, 3379-3393.  [CrossRef] [PubMed] [ChemPort]
Knabe, J., Baldauf, J. & Ahlhelm, A. (1997). Pharmazie, 52, 912-919.  [ChemPort] [PubMed]
Luer, M. S. (1998). Neurol. Res. 20, 178-182.  [Web of Science] [ChemPort] [PubMed]
Matzukura, M., Daiku, Y., Ueda, K., Tanaka, S., Igarashi, T. & Minami, N. (1992). Chem. Pharm. Bull. 40, 1823-1827.  [PubMed]
Moloney, G. P., Martin, G. R., Mathews, N., Milne, A., Hobbs, H., Dosworth, S., Sang, P. Y., Knight, C., Maxwell, M. & Glen, R. (1999). J. Med. Chem. 42, 2504-2526.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Moloney, G. P., Robertson, A. D., Martin, G. R., MacLennan, S., Mathews, N., Dosworth, S., Sang, P. Y., Knight, C. & Glen, R. (2001). J. Med. Chem. 44, 2843-2848.  [Web of Science] [PubMed]
Quan, M. L., Ellis, C. D., He, M. Y., Liauw, A. Y., Woerner, F. J., Alexander, R. S., Knabb, R. M., Lam, P. Y. S. & Luettgen, J. M. (2003). Bioorg. Med. Chem. Lett. 13, 369-373.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Somsák, L., Kovács, L., Tóth, M., Ösz, E., Szilágyi, L., Györgydeak, Z., Dinya, Z., Docsa, T., Tóth, B. & Gergely, P. (2001). J. Med. Chem. 44, 2843-2848.  [Web of Science] [PubMed]
Sutherland, J. C. & Hess, G. P. (2000). Nat. Prod. Rep. 17, 621-631.  [CrossRef] [PubMed] [ChemPort]
Thenmozhiyal, J. C., Wong, P. T. H. & Chui, W. K. (2004). J. Med. Chem. 47, 1527-1535.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Van Poecke, S., Negri, A., Janssens, J., Solaroli, N., Karlsson, A., Gago, F., Balzarini, J. & Van Calenberg, S. (2011). Org. Biomol. Chem. 9, 892-901.  [CrossRef] [ChemPort] [PubMed]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1102-o1103   [ doi:10.1107/S1600536813016000 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.