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Volume 67 
Part 1 
Page o164  
January 2011  

Received 10 December 2010
Accepted 11 December 2010
Online 18 December 2010

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Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.118
Data-to-parameter ratio = 19.6
Details
Open access

4-(1,2,4-Triazol-1-yl)aniline

Hoong-Kun Fun,a*+ Ching Kheng Quah,a++ B. Chandrakantha,b Arun M. Isloorc and Prakash Shettyd

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bDepartment of Chemistry, Manipal Institute of Technology, Manipal 576 104, India,cOrganic Chemistry Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India, and dDepartment of Printing, Manipal Institute of Technology, Manipal 576 104, India
Correspondence e-mail: hkfun@usm.my

In the title compound, C8H8N4, the dihedral angle between the triazole ring [maximum deviation = 0.003 (1) Å] and the benzene ring is 34.57 (7)°. In the crystal, molecules are linked into sheets lying parallel to the ac plane via intermolecular N-H...N and C-H...N hydrogen bonds. Aromatic [pi]-[pi] [centroid-centroid distance = 3.6750 (8) Å] stacking and N-H...[pi] interactions are also observed.

Related literature

For general background to and the biological activity of triazole derivatives, see: Isloor et al. (2000[Isloor, A. M., Kalluraya, B. & Rao, M. (2000). J. Saudi Chem. Soc. 4, 265-270.], 2009[Isloor, A. M., Kalluraya, B. & Shetty, P. (2009). Eur. J. Med. Chem. 44, 3784-3787.]); Soliman et al. (2001[Soliman, R., Habib, N. S., Ashour, F. A. & el-Taiebi, M. (2001). Boll. Chim. Farm. 140, 140-148.]); Holla et al. (2000[Holla, B. S., Akberali, P. M. & Shivananda, M. K. (2000). Farmaco, 55, 256-263.]); Sunil et al. (2009[Sunil, D., Isloor, A. M. & Shetty, P. (2009). Pharma Chem. 1 19-26.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For a related structure, see: Fun et al. (2010[Fun, H.-K., Quah, C. K., Malladi, S. & Isloor, A. M. (2010). Acta Cryst. E66, o2799-o2800.]).

[Scheme 1]

Experimental

Crystal data

  • C8H8N4

  • Mr = 160.18

  • Monoclinic, P 21 /c

  • a = 5.5488 (1) Å

  • b = 7.3656 (2) Å

  • c = 19.5477 (5) Å

  • [beta] = 99.416 (2)°

  • V = 788.15 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.50 × 0.42 × 0.14 mm
Data collection

  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.957, Tmax = 0.988

  • 8036 measured reflections

  • 2160 independent reflections

  • 1722 reflections with I > 2[sigma](I)

  • Rint = 0.030
Refinement

  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.118

  • S = 1.05

  • 2160 reflections

  • 110 parameters

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

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C3-C8 phenyl ring.
D-H...A D-H H...A D...A D-H...A
N4-H2N4...N1i 0.871 (16) 2.208 (16) 3.0709 (18) 171.1 (15)
C1-H1A...N2ii 0.93 2.50 3.4035 (16) 166
N4-H1N4...Cg2iii 0.87 (2) 2.58 (2) 3.3929 (16) 156.0 (17)
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) x-1, y, z; (iii) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. 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 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5764 ).

Acknowledgements

HKF and CKQ thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). CKQ also thanks USM for the award of a USM fellowship. AMI is thankful to the Director of the National Institute of Technology for providing research facilities and also thanks the Board for Research in Nuclear Sciences, Department of Atomic Energy, Government of India, for a Young Scientist Award.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Fun, H.-K., Quah, C. K., Malladi, S. & Isloor, A. M. (2010). Acta Cryst. E66, o2799-o2800.  [CrossRef] [details]
Holla, B. S., Akberali, P. M. & Shivananda, M. K. (2000). Farmaco, 55, 256-263.  [PubMed] [ChemPort]
Isloor, A. M., Kalluraya, B. & Rao, M. (2000). J. Saudi Chem. Soc. 4, 265-270.  [ChemPort]
Isloor, A. M., Kalluraya, B. & Shetty, P. (2009). Eur. J. Med. Chem. 44, 3784-3787.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Soliman, R., Habib, N. S., Ashour, F. A. & el-Taiebi, M. (2001). Boll. Chim. Farm. 140, 140-148.  [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Sunil, D., Isloor, A. M. & Shetty, P. (2009). Pharma Chem. 1 19-26.  [ChemPort]

Acta Cryst (2011). E67, o164  [ doi:10.1107/S1600536810052025 ]

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