[Journal logo]

Volume 69 
Part 2 
Page o262  
February 2013  

Received 21 December 2012
Accepted 9 January 2013
Online 19 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.062
wR = 0.142
Data-to-parameter ratio = 16.2
Details
Open access

1H-Benzotriazol-1-yl 4-{(E)-[4-(dimethylamino)phenyl]diazenyl}benzoate

aLUNAM Université, Université d'Angers, CNRS UMR 6200, Laboratoire MOLTECH-Anjou, CNRS-UMR 6200, 2 bd. Lavoisier, 49045 Angers, France,bInstitute of Solid State Physics, RAS, 142432 Chernogolovka MD, Russian Federation, and cLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane, Faculté des Sciences et Techniques, BP 523, 23000 Beni-Mellal, Morocco
Correspondence e-mail: m.khouili@usms.ma

The title compound, C21H18N6O2, was obtained as a by-product of a reaction between (E)-4-(4-dimethylaminophenylazo)benzoic acid and 2-amino-4-(2-pyridyl)-6-(6-pyridyl)-1,3,5-triazine, which has a very low solubility, under peptidic coupling conditions, using THF as solvent. The condensation reaction occurred between 1-hydroxybenzotriazole and (E)-4-(4-dimethylaminophenylazo)benzoic acid. The dihedral angle between the benzene rings in the (E)-diphenyldiazene fragment is 10.92 (13)° and that between the benzotriazole mean plane and the central benzene ring is 80.57 (7)°. In the crystal, [pi]-[pi] stacking [centroid-centroid distances = 3.823 (2) and 3.863 (2) Å] of similar fragments generates molecular layers parallel to (0-12). The crystal packing also features weak C-H...N hydrogen bonds involving N atoms of the benzotriazole ring.

Related literature

For applications of 1-hydroxybenzotriazole in organic syntheses, see: König & Geiger (1970[König, W. & Geiger, R. (1970). Chem. Ber. 103, 788-798.]); Miyazawa et al. (1984[Miyazawa, T., Otomatsu, T., Yamada, T. & Kuwata, S. (1984). Tetrahedron Lett. 25, 771-772.]); Baldini et al. (2008[Baldini, L., Sansone, F., Faimani, G., Massera, C., Casnati, A. & Ungaro, R. (2008). Eur. J. Org. Chem. 5, 869-886.]). For the use of 1-hydroxybenzotriazole in the preparation of coordination compounds, see: Papaefstathiou et al. (2002[Papaefstathiou, G. S., Vicente, R., Raptopoulou, C. P., Terzis, A., Escuer, A. & Perlepes, S. P. (2002). Eur. J. Inorg. Chem. 9, 2488-2493.]).

[Scheme 1]

Experimental

Crystal data
  • C21H18N6O2

  • Mr = 386.41

  • Triclinic, [P \overline 1]

  • a = 6.6362 (8) Å

  • b = 11.384 (3) Å

  • c = 13.022 (3) Å

  • [alpha] = 99.64 (3)°

  • [beta] = 103.61 (2)°

  • [gamma] = 92.440 (17)°

  • V = 939.2 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.3 × 0.2 × 0.2 mm

Data collection
  • Bruker KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.697, Tmax = 0.746

  • 18381 measured reflections

  • 4288 independent reflections

  • 2107 reflections with I > 2[sigma](I)

  • Rint = 0.059

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.142

  • S = 1.04

  • 4288 reflections

  • 264 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4...N5i 0.93 2.63 3.415 (3) 142
C23-H23...N6ii 0.93 2.63 3.560 (3) 176
Symmetry codes: (i) -x+1, -y, -z+2; (ii) x+1, y, z.

Data collection: COLLECT (Hooft, 1998[Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DIRAX (Duisenberg, 1992[Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96.]); data reduction: EVALCCD (Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]); 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: DIAMOND (Brandenburg, 2005[Brandenburg, K. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: 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: ZQ2193 ).


Acknowledgements

The authors acknowledge the CNRST (Morocco) for partial financial support

References

Baldini, L., Sansone, F., Faimani, G., Massera, C., Casnati, A. & Ungaro, R. (2008). Eur. J. Org. Chem. 5, 869-886.  [CrossRef]
Brandenburg, K. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96.  [CrossRef] [ChemPort] [ISI] [details]
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.  [ISI] [CrossRef] [ChemPort] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
König, W. & Geiger, R. (1970). Chem. Ber. 103, 788-798.  [PubMed]
Miyazawa, T., Otomatsu, T., Yamada, T. & Kuwata, S. (1984). Tetrahedron Lett. 25, 771-772.  [CrossRef] [ChemPort] [ISI]
Papaefstathiou, G. S., Vicente, R., Raptopoulou, C. P., Terzis, A., Escuer, A. & Perlepes, S. P. (2002). Eur. J. Inorg. Chem. 9, 2488-2493.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o262  [ doi:10.1107/S1600536813000846 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.