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

Hernández-Ortega, S.; Cuenú-Cabezas, F.; Abonia-González, R.; Cabrera-Ortiz, A.

doi:10.1107/S1600536812042791

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 (C-C) = 0.002 Å
R = 0.040
wR = 0.115
Data-to-parameter ratio = 13.7
Details

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

Simón Hernández-Ortega,^a ^* Fernando Cuenú-Cabezas,^b Rodrigo Abonia-González ^c and Armando Cabrera-Ortiz ^a

^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-HN and N-HO hydrogen bonds, forming sheets in the bc plane. In addition, a weak C-HN interaction is observed.

Related literature

For background to pyrazole-based ligands, see; Ahmed et al. (2005); Abonia et al. (2002, 2004, 2010); Guerrero et al. (2009); Quiroga et al. (2008); Schutznerová, et al. (2012). For structure of an isomer of the title compound, see: Low et al. (2004).

Experimental

Crystal data

C₁₃H₁₆N₄O₂
M_r = 260.30
Monoclinic, P 2₁ /c
a = 11.9421 (14) Å
b = 9.6419 (11) Å
c = 11.7694 (13) Å
= 93.504 (2)°
V = 1352.6 (3) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.044

Refinement

R[F² > 2(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
_max = 0.17 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N4-H4AN2ⁱ	0.90 (1)	2.23 (1)	3.1195 (17)	172 (2)
N4-H4BO1ⁱⁱ	0.90 (1)	2.39 (1)	3.241 (2)	160 (2)
C14-H14N4ⁱⁱⁱ	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); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); 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.
Abonia, R., Rengifo, E., Quiroga, J., Insuasty, B., Cobo, J. & Nogueras, M. (2004). Tetrahedron, 60, 8839-8843.
Abonia, R., Rengifo, E., Quiroga, J., Insuasty, B., Sanchez, A., Cobo, J., Low, J. N. & Nogueras, M. (2002). Tetrahedron Lett. 43, 5617-5620.
Ahmed, M. S. M., Kobayashi, K. & Mori, A. (2005). Org. Lett. 7, 4487-4489.
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.
Low, J. N., Cobo, J., Abonia, R., Quiroga, J. & Glidewell, C. (2004). Acta Cryst. C60, o194-o195.
Quiroga, J., Portilla, J., Abonia, R., Insuasty, B., Nogueras, M. & Cobo, J. (2008). Tetrahedron Lett. 49, 6254-6256.
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.

organic compounds