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Volume 69 
Part 11 
Page o1724  
November 2013  

Received 7 October 2013
Accepted 25 October 2013
Online 31 October 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.007 Å
R = 0.046
wR = 0.138
Data-to-parameter ratio = 5.8
Details
Open access

1-[5-Methyl-1-(4-nitro­phen­yl)-1H-1,2,3-triazol-4-yl]ethanone

aDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India, and bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
Correspondence e-mail: dr@physics.uni-mysore.ac.in

The asymmetric unit of the title compound, C11H10N4O3, contains two independent mol­ecules in which the benzene rings make dihedral angles of 38.3 (2) and 87.1 (2)° with respect to the triazole rings. In the crystal, the mol­ecules are linked by C-H...O hydrogen bonds, forming chains along [021]. Further, weak C-O...[pi] [3.865 (5) Å, 83.8 (3)°] and N-O...[pi] [3.275 (5) and 3.240 (6) Å, 141.8 (4) and 102.8 (3)°] inter­actions are observed.

Related literature

For chemical and biological properties and pharmocological applications of 1,2,3-triazole derivative, see: Nithinchandra et al. (2012[Nithinchandra, Kalluraya, B., Aamir, S. & Shabaraya, A. R. (2012). Eur. J. Med. Chem. 54, 597-604.], 2013[Nithinchandra, Kalluraya, B., Shobhitha, S. & Babu, M. (2013). J. Chem. Pharm. Res. 5, 307-313.]); Biagi et al. (2004[Biagi, G., Calderone, V., Giorgi, I., Livi, O., Martinotti, E., Martelli, A. & Nardi, A. (2004). Farmaco, 59, 397-404.]); Manfredini et al. (2000[Manfredini, S., Vicentini, C. B., Manfrini, M., Bianchi, N., Rutigliano, C., Mischiati, C. & Gambari, R. (2000). Bioorg. Med. Chem. 8, 2343-2346.]); Sherement et al. (2004[Sherement, E. A., Tomanov, R. I., Trukhin, E. V. & Berestovitskaya, V. M. (2004). Russ. J. Org. Chem. 40, 594-595.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Prpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C11H10N4O3

  • Mr = 246.23

  • Orthorhombic, P c a 21

  • a = 7.2786 (10) Å

  • b = 11.5055 (16) Å

  • c = 27.220 (4) Å

  • V = 2279.5 (6) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 0.91 mm-1

  • T = 296 K

  • 0.23 × 0.22 × 0.21 mm

Data collection
  • Bruker X8 Proteum diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.]) Tmin = 0.818, Tmax = 0.831

  • 8697 measured reflections

  • 1910 independent reflections

  • 1617 reflections with I > 2[sigma](I)

  • Rint = 0.057

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.138

  • S = 1.08

  • 1910 reflections

  • 329 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [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
C5B-H5B1...O3Ai 0.96 2.51 3.306 (8) 141
C10B-H10B...O1A 0.93 2.58 3.197 (7) 124
Symmetry code: (i) [-x+{\script{1\over 2}}, y-1, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). 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: 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: Mercury.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5313 ).


Acknowledgements

The authors are thankful to the IOE, University of Mysore, for providing the single-crystal X-ray diffraction facility. VN is grateful to the UGC for the award of an RFSMS Fellowship. RD acknowledges the UGC, New Delhi, for financial support under the Major Research Project Scheme [UGC MRP No. F.41-882/2012 (SR) dated 01/07/2012].

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Prpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Biagi, G., Calderone, V., Giorgi, I., Livi, O., Martinotti, E., Martelli, A. & Nardi, A. (2004). Farmaco, 59, 397-404.  [CrossRef] [PubMed] [ChemPort]
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Manfredini, S., Vicentini, C. B., Manfrini, M., Bianchi, N., Rutigliano, C., Mischiati, C. & Gambari, R. (2000). Bioorg. Med. Chem. 8, 2343-2346.  [CrossRef] [PubMed] [ChemPort]
Nithinchandra, Kalluraya, B., Aamir, S. & Shabaraya, A. R. (2012). Eur. J. Med. Chem. 54, 597-604.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Nithinchandra, Kalluraya, B., Shobhitha, S. & Babu, M. (2013). J. Chem. Pharm. Res. 5, 307-313.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sherement, E. A., Tomanov, R. I., Trukhin, E. V. & Berestovitskaya, V. M. (2004). Russ. J. Org. Chem. 40, 594-595.


Acta Cryst (2013). E69, o1724  [ doi:10.1107/S1600536813029425 ]

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