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Volume 68 
Part 11 
Page o3171  
November 2012  

Received 10 October 2012
Accepted 12 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.115
Data-to-parameter ratio = 13.7
Details
Open access

3-tert-Butyl-1-(3-nitrophenyl)-1H-pyrazol-5-amine

aInstituto de Química, Universidad Nacional Autónoma de México, circuito exterior, ciudad universitaria, México 04510, México,bLaboratorio de Química Inorgánica y Catálisis, Programa de Química, Universidad del Quindio, Avenida Bolivar Calle 12 Norte, Armenia, Colombia, and cDepartamento de Química, Universidad del Valle, A. A. 25360, Cali, Colombia
Correspondence e-mail: simonho@unam.mx

In the title compound, C13H16N4O2, the pyrazole ring forms a dihedral angle of 50.61 (6)° with the 3-nitro-phenyl ring. The plane of the nitro group is twisted by 6.8 (7)° out of the plane of the phenyl ring. In the crystal, the molecules are linked by N-H...N and N-H...O hydrogen bonds, forming sheets in the bc plane. In addition, a weak C-H...N interaction is observed.

Related literature

For background to pyrazole-based ligands, see; Ahmed et al. (2005[Ahmed, M. S. M., Kobayashi, K. & Mori, A. (2005). Org. Lett. 7, 4487-4489.]); Abonia et al. (2002[Abonia, R., Rengifo, E., Quiroga, J., Insuasty, B., Sanchez, A., Cobo, J., Low, J. N. & Nogueras, M. (2002). Tetrahedron Lett. 43, 5617-5620.], 2004[Abonia, R., Rengifo, E., Quiroga, J., Insuasty, B., Cobo, J. & Nogueras, M. (2004). Tetrahedron, 60, 8839-8843.], 2010[Abonia, R., Castillo, J., Insuasty, B., Quiroga, J., Nogueras, M. & Cobo, J. (2010). Eur. J. Org. Chem. 33, 6454-6463.]); Guerrero et al. (2009[Guerrero, M., Pons, J., Parella, T., Font-Bardia, M., Calvet, T. & Ros, J. (2009). Inorg. Chem. 48, 8736-8750.]); Quiroga et al. (2008[Quiroga, J., Portilla, J., Abonia, R., Insuasty, B., Nogueras, M. & Cobo, J. (2008). Tetrahedron Lett. 49, 6254-6256.]); Schutznerová, et al. (2012[Schutznerová, E., Popa, I., Krystof, V., Koshino, H., Trávnícek, Z., Hradil, P. & Cankar, P. (2012). Tetrahedron, 68, 3996-4002.]). For structure of an isomer of the title compound, see: Low et al. (2004[Low, J. N., Cobo, J., Abonia, R., Quiroga, J. & Glidewell, C. (2004). Acta Cryst. C60, o194-o195.]).

[Scheme 1]

Experimental

Crystal data
  • C13H16N4O2

  • Mr = 260.30

  • Monoclinic, P 21 /c

  • a = 11.9421 (14) Å

  • b = 9.6419 (11) Å

  • c = 11.7694 (13) Å

  • [beta] = 93.504 (2)°

  • V = 1352.6 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 298 K

  • 0.46 × 0.36 × 0.32 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • 14529 measured reflections

  • 2486 independent reflections

  • 2036 reflections with I > 2[sigma](I)

  • Rint = 0.044

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.115

  • S = 1.05

  • 2486 reflections

  • 181 parameters

  • 2 restraints

  • 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
N4-H4A...N2i 0.90 (1) 2.23 (1) 3.1195 (17) 172 (2)
N4-H4B...O1ii 0.90 (1) 2.39 (1) 3.241 (2) 160 (2)
C14-H14...N4iii 0.93 2.54 3.403 (2) 155
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: SMART (Bruker, 1999[Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6847 ).


Acknowledgements

FCC and RAG thanks the Universidad del Valle and the Universidad del Quindío for financial support to project 542. ACO thanks the DGAPA-UNAM for financial support (PAPIIT IN203209). SHO thanks the Consejo Superior de Investigaciones Científicas (CSIC) of Spain for the award of a licence for the use of the Cambridge Structural Database.

References

Abonia, R., Castillo, J., Insuasty, B., Quiroga, J., Nogueras, M. & Cobo, J. (2010). Eur. J. Org. Chem. 33, 6454-6463.  [CrossRef]
Abonia, R., Rengifo, E., Quiroga, J., Insuasty, B., Cobo, J. & Nogueras, M. (2004). Tetrahedron, 60, 8839-8843.  [ISI] [CrossRef] [ChemPort]
Abonia, R., Rengifo, E., Quiroga, J., Insuasty, B., Sanchez, A., Cobo, J., Low, J. N. & Nogueras, M. (2002). Tetrahedron Lett. 43, 5617-5620.  [ISI] [CrossRef] [ChemPort]
Ahmed, M. S. M., Kobayashi, K. & Mori, A. (2005). Org. Lett. 7, 4487-4489.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Guerrero, M., Pons, J., Parella, T., Font-Bardia, M., Calvet, T. & Ros, J. (2009). Inorg. Chem. 48, 8736-8750.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Low, J. N., Cobo, J., Abonia, R., Quiroga, J. & Glidewell, C. (2004). Acta Cryst. C60, o194-o195.  [CSD] [CrossRef] [details]
Quiroga, J., Portilla, J., Abonia, R., Insuasty, B., Nogueras, M. & Cobo, J. (2008). Tetrahedron Lett. 49, 6254-6256.  [ISI] [CrossRef] [ChemPort]
Schutznerová, E., Popa, I., Krystof, V., Koshino, H., Trávnícek, Z., Hradil, P. & Cankar, P. (2012). Tetrahedron, 68, 3996-4002.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3171  [ doi:10.1107/S1600536812042791 ]

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