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Volume 69 
Part 8 
Page o1339  
August 2013  

Received 28 May 2013
Accepted 18 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.042
wR = 0.112
Data-to-parameter ratio = 12.9
Details
Open access

3-Amino-4-(1,3-benzoxazol-2-yl)-5-(cyclohexylamino)thiophene-2-carbonitrile

aLaboratoire de Chimie Organique Physique, Département de Chimie, Faculté des Sciences de Sfax, Université de Sfax, BP 1171, 3000 Sfax, Tunisia, and bLaboratoire Physico-Chimie de l'Etat Solide, Département de Chimie, Faculté des Sciences de Sfax, Université de Sfax, BP 1171, 3000 Sfax, Tunisia
Correspondence e-mail: belhouchet2002@yahoo.fr

In the title compound, C18H18N4OS, the cyclohexyl ring adopts a chair conformation. The other rings of this compound lie almost in the same plane, with a mean deviation of 0.03 (2) Å from the least-squares plane defined by the 14 constituent atoms. There are intramolecular N-H...N and N-H...O hydrogen bonds, as well as intermolecular N-H...N hydrogen bonds, which link the molecules into centrosymmetric dimers.

Related literature

For the pharmacological and biological activities of benzoxazole derivatives, see: Isomura et al. (1983[Isomura, Y., Ito, N., Homma, H., Abe, T. & Kubo, K. (1983). Chem. Pharm. Bull. 31, 3618-3178.]); Cheng et al.(1993[Cheng, C. C., Liu, D. E. & Chou, T. C. (1993). Heterocycles, 35, 775-789.]); Koci et al. (2002[Koci, J., Klimesova, V., Waisser, K., Kaustova, J., Dahse, H. M. & Mollmann, U. (2002). Bioorg. Med. Chem. Lett. 12, 3275-3278.]); Hoffman et al. (1993[Hoffman, J. M., Smith, A. M., Rooney, C. S., Fisher, T. E., Wai, J. S., Thomas, C. M., Bamberger, D. L. & Anderson, P. S. (1993). J. Med. Chem. 36, 953-966.]); Arpaci et al. (2002[Arpaci, T., Yalcin, I. & Altanlar, N. (2002). Arch. Pharm. 57, 283-288.]). For the synthesis and a similar structure, see: Youssef et al. (2011[Youssef, C., BenAmmar, H., Belhouchet, M., Beydoun, K., Ben Salem, R., Doucet, H. & Dixneuf, P. H. (2011). J. Heterocycl. Chem. 48, 1126-1131.]); Belhouchet et al. (2012[Belhouchet, M., Youssef, C., Ben Ammar, H., Ben Salem, R. & Mhiri, T. (2012). X-ray Struct. Anal. Online, 28, 3-4.]).

[Scheme 1]

Experimental

Crystal data
  • C18H18N4OS

  • Mr = 338.42

  • Monoclinic, C 2/c

  • a = 24.270 (5) Å

  • b = 6.193 (5) Å

  • c = 23.578 (5) Å

  • [beta] = 107.554 (5)°

  • V = 3379 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 293 K

  • 0.3 × 0.25 × 0.22 mm

Data collection
  • Bruker APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.655, Tmax = 0.746

  • 13506 measured reflections

  • 2961 independent reflections

  • 1904 reflections with I > 2[sigma](I)

  • Rint = 0.049

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.112

  • S = 1.01

  • 2961 reflections

  • 230 parameters

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

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H1N2...O1 0.92 (3) 2.13 (3) 2.783 (4) 127 (2)
N2-H2N2...N1i 0.86 (3) 2.25 (3) 3.088 (4) 166 (3)
N3-H1N3...N4 0.86 (2) 2.12 (3) 2.787 (3) 135 (2)
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); 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: BV2222 ).


References

Arpaci, T., Yalcin, I. & Altanlar, N. (2002). Arch. Pharm. 57, 283-288.
Belhouchet, M., Youssef, C., Ben Ammar, H., Ben Salem, R. & Mhiri, T. (2012). X-ray Struct. Anal. Online, 28, 3-4.  [CrossRef] [ChemPort]
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cheng, C. C., Liu, D. E. & Chou, T. C. (1993). Heterocycles, 35, 775-789.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Hoffman, J. M., Smith, A. M., Rooney, C. S., Fisher, T. E., Wai, J. S., Thomas, C. M., Bamberger, D. L. & Anderson, P. S. (1993). J. Med. Chem. 36, 953-966.  [CrossRef] [ChemPort] [PubMed]
Isomura, Y., Ito, N., Homma, H., Abe, T. & Kubo, K. (1983). Chem. Pharm. Bull. 31, 3618-3178.
Koci, J., Klimesova, V., Waisser, K., Kaustova, J., Dahse, H. M. & Mollmann, U. (2002). Bioorg. Med. Chem. Lett. 12, 3275-3278.  [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Youssef, C., BenAmmar, H., Belhouchet, M., Beydoun, K., Ben Salem, R., Doucet, H. & Dixneuf, P. H. (2011). J. Heterocycl. Chem. 48, 1126-1131.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1339  [ doi:10.1107/S1600536813019880 ]

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