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Volume 68 
Part 11 
Page o3162  
November 2012  

Received 5 October 2012
Accepted 11 October 2012
Online 20 October 2012

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Key indicators
Single-crystal X-ray study
T = 193 K
Mean [sigma](C-C) = 0.005 Å
R = 0.059
wR = 0.122
Data-to-parameter ratio = 13.2
Details
Open access

Di-tert-butyl N-{[1-(pyridin-4-yl)-1H-1,2,3-triazol-4-yl]methyl}iminodiacetate

Alison François,a Louise Marty,a Claude Picard,a Sonia Mallet-Ladeirab and Eric Benoista*

aLSPCMIB, UMR-CNRS 5068, Université de Toulouse, 118 route de Narbonne, F-31062 Toulouse cedex 9, and bUniversité de Toulouse, UPS and CNRS, Institut de Chimie de Toulouse, FR2599, 118 route de Narbonne, F-31062 Toulouse cedex 9, France
Correspondence e-mail: benoist@chimie.ups-tlse.fr

In the title compound, C20H29N5O4, the pyridine ring makes a dihedral angle of 10.41 (16)° with the triazole ring, which exhibits an azo-like character. In the crystal, molecules are linked by C-H...O and C-H...N hydrogen bonds, and C-H...[pi] interactions involving a methyl group and the pyridine ring of a neighbouring molecule, leading to the formation of a three-dimensional network.

Related literature

For 4-pyridyl-1,2,3-triazoles as building blocks in the synthesis of chelating agents for biomedical applications, see: Bonnet et al. (2012[Bonnet, C. S., Buron, F., Caille, F., Shade, C. M., Drahos, B., Pellegatti, L., Zhang, J., Villette, S., Helm, L., Pichon, C., Suzenet, F., Petoud, S. & Toth, E. (2012). Chem. Eur. J. 18, 1419-1431.]); Pellegatti et al. (2008[Pellegatti, L., Zhang, J., Drahos, B., Villette, S., Suzenet, F., Guillaumet, G., Petoud, S. & Toth, E. (2008). Chem. Commun. pp. 6591-6593.]). For the crystal structures of structural isomers such as 2-pyridyl-1,2,3-triazoles, see: Obata et al. (2008[Obata, M., Kitamura, A., Mori, A., Kameyama, C., Czaplewska, J. A., Tanaka, R., Kinoshita, I., Kusumoto, T., Hashimoto, H., Harada, M., Mikata, Y., Funabiki, T. & Yano, S. (2008). Dalton Trans. pp. 3292-3300.]); Schweinfurth et al. (2008[Schweinfurth, D., Hardcastle, K. I. & Bunz, U. H. F. (2008). Chem. Commun. pp. 2203-2205.]); Boulay et al. (2010[Boulay, A., Seridi, A., Zedde, C., Ladeira, S., Picard, C., Maron, L. & Benoist, E. (2010). Eur. J. Inorg. Chem. pp. 5058-5062.]); Seridi et al. (2011[Seridi, A., Wolff, M., Boulay, A., Saffon, N., Coulais, Y., Picard, C., Machura, B. & Benoist, E. (2011). Inorg. Chem. Commun. 14, 238-242.]); Crowley et al. (2010[Crowley, J. D., Bandeen, P. H. & Hanton, L. R. (2010). Polyhedron, 29, 70-83.]); Kilpin et al. (2011[Kilpin, K. J., Gavey, E. L., McAdam, C. J., Anderson, C. B., Lind, S. J., Keep, C. C., Gordon, K. C. & Crowley, J. D. (2011). Inorg. Chem. 50, 6334-6346.]).

[Scheme 1]

Experimental

Crystal data

  • C20H29N5O4

  • Mr = 403.48

  • Monoclinic, P 21

  • a = 9.1568 (8) Å

  • b = 11.4452 (10) Å

  • c = 11.4928 (11) Å

  • [beta] = 110.840 (4)°

  • V = 1125.66 (18) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 193 K

  • 0.2 × 0.1 × 0.04 mm
Data collection

  • Bruker Kappa APEXII Quazar diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.989, Tmax = 0.997

  • 11329 measured reflections

  • 3530 independent reflections

  • 1947 reflections with I > 2[sigma](I)

  • Rint = 0.077
Refinement

  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.122

  • S = 1.00

  • 3530 reflections

  • 268 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C1-C5 ring.
D-H...A D-H H...A D...A D-H...A
C2-H2...O1i 0.95 2.54 3.443 (4) 160
C6-H6...N1ii 0.95 2.31 3.252 (4) 173
C9-H9B...N3iii 0.99 2.50 3.449 (4) 160
C18-H18A...Cg1iv 0.98 2.91 3.864 (4) 166
Symmetry codes: (i) x, y+1, z; (ii) [-x+2, y-{\script{1\over 2}}, -z+2]; (iii) [-x+1, y-{\script{1\over 2}}, -z+1]; (iv) x, y-1, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2008[Bruker (2008). 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: WinGX publication routines (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2510 ).

Acknowledgements

We gratefully acknowledge the French Ministère de l'Education Nationale, de la Recherche et de la Technologie for financial support.

References

Bonnet, C. S., Buron, F., Caille, F., Shade, C. M., Drahos, B., Pellegatti, L., Zhang, J., Villette, S., Helm, L., Pichon, C., Suzenet, F., Petoud, S. & Toth, E. (2012). Chem. Eur. J. 18, 1419-1431.  [CrossRef] [ChemPort] [PubMed]
Boulay, A., Seridi, A., Zedde, C., Ladeira, S., Picard, C., Maron, L. & Benoist, E. (2010). Eur. J. Inorg. Chem. pp. 5058-5062.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Crowley, J. D., Bandeen, P. H. & Hanton, L. R. (2010). Polyhedron, 29, 70-83.  [ISI] [CSD] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kilpin, K. J., Gavey, E. L., McAdam, C. J., Anderson, C. B., Lind, S. J., Keep, C. C., Gordon, K. C. & Crowley, J. D. (2011). Inorg. Chem. 50, 6334-6346.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Obata, M., Kitamura, A., Mori, A., Kameyama, C., Czaplewska, J. A., Tanaka, R., Kinoshita, I., Kusumoto, T., Hashimoto, H., Harada, M., Mikata, Y., Funabiki, T. & Yano, S. (2008). Dalton Trans. pp. 3292-3300.  [CSD] [CrossRef]
Pellegatti, L., Zhang, J., Drahos, B., Villette, S., Suzenet, F., Guillaumet, G., Petoud, S. & Toth, E. (2008). Chem. Commun. pp. 6591-6593.  [CrossRef]
Schweinfurth, D., Hardcastle, K. I. & Bunz, U. H. F. (2008). Chem. Commun. pp. 2203-2205.  [CSD] [CrossRef]
Seridi, A., Wolff, M., Boulay, A., Saffon, N., Coulais, Y., Picard, C., Machura, B. & Benoist, E. (2011). Inorg. Chem. Commun. 14, 238-242.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]

Acta Cryst (2012). E68, o3162  [ doi:10.1107/S1600536812042596 ]

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