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Volume 69 
Part 5 
Page o761  
May 2013  

Received 26 March 2013
Accepted 13 April 2013
Online 20 April 2013

Key indicators
Single-crystal X-ray study
T = 300 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.062
wR = 0.207
Data-to-parameter ratio = 11.6
Details
Open access

tert-Butyl 4-{5-[3-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-3-yl}piperazine-1-carboxylate

aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India,bDepartment of Physics, Governament First Grade College K.R. Pete, Karnataka 571 426, India,cDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, and dDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India
Correspondence e-mail: palaksha.bspm@gmail.com

In the title compound, C18H21F3N4O4, the piperazine ring adopts a chair conformation and the dihedral angle between the oxadiazole and benzene rings is 6.45 (14)°. The C atoms and their attached H atoms in the piperazine ring are disordered, with site-occupation factors of 0.576 (12) and 0.424 (12). In the crystal, molecules are linked through weak C-H...O interactions, generating an R22(12) motif. Further, secondary C-H...O intermolecular interactions link the molecules into C(6) chains along [100].

Related literature

For the synthesis and biological activity of 1,2,4-oxadiazoles, see: Chimirri et al. (1996[Chimirri, A., Grasso, S., Molica, C., Monforte, A. M., Monforte, P., Zappalà, M. & Scopelliti, R. (1996). Il Farmaco, 51, 279-82.]); Nicolaides et al. (1998[Nicolaides, D. N., Fylaktakidou, K. C., Litinas, K. E. & Hadjipavlou-Litina, D. (1998). Eur. J. Med. Chem. 33, 715-724.]); Kemnitzer et al. (2009[Kemnitzer, W., Kuemmerle, J., Zhang, H. Z., Kasibhatla, S., Tseng, B., Drewe, J. & Cai, S. X. (2009). Bioorg. Med. Chem. Lett. 19, 4410-4415.]).

[Scheme 1]

Experimental

Crystal data
  • C18H21F3N4O4

  • Mr = 414.39

  • Triclinic, [P \overline 1]

  • a = 5.773 (2) Å

  • b = 11.168 (5) Å

  • c = 15.991 (7) Å

  • [alpha] = 96.092 (16)°

  • [beta] = 100.316 (14)°

  • [gamma] = 91.333 (14)°

  • V = 1007.7 (8) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 300 K

  • 0.28 × 0.24 × 0.18 mm

Data collection
  • Bruker SMART X2S diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.968, Tmax = 0.980

  • 7493 measured reflections

  • 3521 independent reflections

  • 2233 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.207

  • S = 1.10

  • 3521 reflections

  • 303 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C17-H17A...O4i 0.96 2.56 3.393 (3) 145
C10A-H10C...O4ii 0.97 2.46 3.413 (10) 167
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: 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: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6899 ).


Acknowledgements

The authors thank Dr S. C. Sharma, Vice Chancellor, Tumkur University, for his constant encouragement and Professor T. N. Guru Row and Vijith Kumar, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for their help and valuable suggestions. BSPM thanks Dr H. C. Devarajegowda, Department of Physics, Yuvarajas College (constituent), University of Mysore, for his guidance.

References

Bruker (2009). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chimirri, A., Grasso, S., Molica, C., Monforte, A. M., Monforte, P., Zappalà, M. & Scopelliti, R. (1996). Il Farmaco, 51, 279-82.  [ChemPort] [PubMed]
Kemnitzer, W., Kuemmerle, J., Zhang, H. Z., Kasibhatla, S., Tseng, B., Drewe, J. & Cai, S. X. (2009). Bioorg. Med. Chem. Lett. 19, 4410-4415.  [CrossRef] [PubMed] [ChemPort]
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]
Nicolaides, D. N., Fylaktakidou, K. C., Litinas, K. E. & Hadjipavlou-Litina, D. (1998). Eur. J. Med. Chem. 33, 715-724.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o761  [ doi:10.1107/S1600536813010131 ]

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