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Volume 68 
Part 12 
Page o3278  
December 2012  

Received 6 September 2012
Accepted 24 October 2012
Online 3 November 2012

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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.103
Data-to-parameter ratio = 16.7
Details
Open access

2-(5,6-Diphenyl-1,2,4-triazin-3-yl)aniline

Mariusz Mojzych,a Zbigniew Karczmarzyka* and Andrzej Fruzinskib

aDepartment of Chemistry, Siedlce University, ul. 3 Maja 54, 08-110 Siedlce, Poland, and bDepartment of General and Ecological Chemistry, Technical University, ul. Zeromskiego 115, 90-924 Lódz, Poland
Correspondence e-mail: kar@uph.edu.pl

The title compound, C21H16N4, obtained under standard Suzuki cross-coupling conditions, is a model compound in the synthesis and biological activity evaluation of new aza-analogues of sildenafil containing a pyrazolo[4,3-e][1,2,4]triazine system. An N-H...N intramolecular hydrogen bond involving the aminobenzene system and the 1,2,4-triazine moiety helps to establish a near coplanar orientation of the rings with a dihedral angle of 12.04 (4)°, which is believed to be necessary for the biological activity of sildenafil analogues. The 1,2,4-triazine ring is slightly distorted from planarity [r.m.s deviation = 0.0299 (11) Å] and forms dihedral angles of 58.60 (4) and 36.35 (3)° with the pendant phenyl rings. The crystal packing features bifurcated N-H...(N,N) hydrogen bonds linking screw-axis-related molecules into chains parallel to the [010] direction< and [pi]-[pi] interactions, with a centroid-centroid separation of 3.8722 (7) Å and a slippage of 1.412 (3) Å. The crystal studied was a nonmerohedral twin with a ratio of 0.707 (2):0293 (2).

Related literature

For background information on the activity of sildenafil citrate, see: Terrett et al. (1996[Terrett, N. K., Bell, A. S., Brown, D. & Ellis, P. (1996). Bioorg. Med. Chem. Lett. 6, 1819-1824.]); Card et al. (2004[Card, G. L., England, B. P., Suzuki, Y., Fong, D., Powell, B., Lee, B., Luu, C., Tabrizizad, M., Gillette, S., Ibrahim, P. N., Artis, D. R., Bollag, G., Milburn, M. V., Kim, S. H., Schlessinger, J. & Zhang, K. Y. (2004). Structure, 12, 2233-2247.]). For the synthesis of the title compound, see: Agarwal et al. (2010[Agarwal, P. K., Saifuddin, M. & Kundu, B. (2010). Tetrahedron, 66, 862-870.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]); Bruno et al. (2002[Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389-397.]).

[Scheme 1]

Experimental

Crystal data

  • C21H16N4

  • Mr = 324.38

  • Monoclinic, P 21 /c

  • a = 11.8797 (3) Å

  • b = 6.0788 (1) Å

  • c = 23.8710 (5) Å

  • [beta] = 101.489 (1)°

  • V = 1689.29 (6) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.61 mm-1

  • T = 293 K

  • 0.21 × 0.14 × 0.01 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.906, Tmax = 1.000

  • 4591 measured reflections

  • 3173 independent reflections

  • 2837 reflections with I > 2[sigma](I)
Refinement

  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.103

  • S = 1.05

  • 4591 reflections

  • 275 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.10 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N7-H72...N2 0.94 (2) 2.00 (2) 2.7037 (19) 130 (2)
N7-H71...N1i 0.93 (3) 2.26 (3) 3.1779 (19) 169 (2)
N7-H71...N2i 0.93 (3) 2.49 (2) 3.2677 (18) 141.3 (19)
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x, -y, -z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LR2082 ).

Acknowledgements

This research was supported by grant No. NN405 092340 from the National Science Centre, Poland.

References

Agarwal, P. K., Saifuddin, M. & Kundu, B. (2010). Tetrahedron, 66, 862-870.  [ISI] [CrossRef] [ChemPort]
Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389-397.  [ISI] [CrossRef] [details]
Card, G. L., England, B. P., Suzuki, Y., Fong, D., Powell, B., Lee, B., Luu, C., Tabrizizad, M., Gillette, S., Ibrahim, P. N., Artis, D. R., Bollag, G., Milburn, M. V., Kim, S. H., Schlessinger, J. & Zhang, K. Y. (2004). Structure, 12, 2233-2247.  [ISI] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Terrett, N. K., Bell, A. S., Brown, D. & Ellis, P. (1996). Bioorg. Med. Chem. Lett. 6, 1819-1824.  [CrossRef]

Acta Cryst (2012). E68, o3278  [ doi:10.1107/S1600536812044194 ]

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