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Volume 64 
Part 9 
Page o1843  
September 2008  

Received 25 July 2008
Accepted 25 August 2008
Online 30 August 2008

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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.063
wR = 0.149
Data-to-parameter ratio = 17.0
Details
Open access

5-Methyl-1-phenyl-1H-1,2,3-triazole-4-carboxylic acid

Jin Rui Lin,a Ji Yuan Yaoa and Hong Zhaoa*

aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
Correspondence e-mail: zhaohong@seu.edu.cn

The title compound, C10H9N3O2, was synthesized from azidobenzene and ethyl acetylacetate. A pair of hydrogen bonds [2.617 (2) Å] interconnects a pair of the carboxyl groups, forming an R22(8) inversion dimer, a frequent motif in carboxylic acids. In the title structure, the bonding H atom in the aforementioned O-H...O hydrogen bond is significantly shifted towards the acceptor O atom [the donor and acceptor O-H distances are 1.25 (4) and 1.38 (4) Å, respectively]. A plot of the O...O versus O-H distances in compounds with paired carboxyl groups shows that the title structure belongs to the group of structures with abnormally long O-H distances with regard to the O...O contacts. The displacement of the bonding H atom towards the centre of the hydrogen bond is concomitant with more equal C-O bonding distances in the carboxyl group.

Related literature

For related literature, see: El Khadem et al. (1968[El Khadem, H., Mansour, H. A. R. & Meshreki, M. H. (1968). J. Chem. Soc. C, pp. 1329-1331.]); Olesen et al. (2003[Olesen, P. H., Sorensen, A. R., Urso, B., Kurtzhals, P., Bowler, A. N., Ehrbar, U. & Hansen, B. F. (2003). J. Med. Chem. 46, 3333-3341.]); Tian et al. (2005[Tian, L., Sun, Y., Li, H., Zheng, X., Cheng, Y., Liu, X. & Qian, B. (2005). J. Inorg. Biochem. 99, 1646-1652.]); Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]); Etter et al. (1990[Etter, M. C., MacDonald, J. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Radl et al. (2000[Radl, S., Hezky, P., Konvicka, P. & Krejci, J. (2000). Collect. Czech. Chem. Commun. 65, 1093-1108.]).

[Scheme 1]

Experimental

Crystal data

  • C10H9N3O2

  • Mr = 203.20

  • Monoclinic, C 2/c

  • a = 23.616 (3) Å

  • b = 7.7189 (15) Å

  • c = 12.606 (2) Å

  • [beta] = 113.18 (3)°

  • V = 2112.5 (8) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 (2) K

  • 0.20 × 0.18 × 0.15 mm
Data collection

  • Rigaku SCXmini diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.965, Tmax = 0.977

  • 10370 measured reflections

  • 2400 independent reflections

  • 1583 reflections with I > 2[sigma](I)

  • Rint = 0.053
Refinement

  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.148

  • S = 1.08

  • 2400 reflections

  • 141 parameters

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

  • [Delta][rho]max = 0.14 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
O2-H2...O1i 1.25 (4) 1.38 (4) 2.617 (2) 173 (3)
Symmetry code: (i) [-x+1, y, -z+{\script{3\over 2}}].

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL/PC (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL/PC.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2106 ).

Acknowledgements

This work was supported by a start-up grant from Southeast University to HZ.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
El Khadem, H., Mansour, H. A. R. & Meshreki, M. H. (1968). J. Chem. Soc. C, pp. 1329-1331.
Etter, M. C., MacDonald, J. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [details]
Olesen, P. H., Sorensen, A. R., Urso, B., Kurtzhals, P., Bowler, A. N., Ehrbar, U. & Hansen, B. F. (2003). J. Med. Chem. 46, 3333-3341.  [ISI] [CrossRef] [PubMed] [ChemPort]
Radl, S., Hezky, P., Konvicka, P. & Krejci, J. (2000). Collect. Czech. Chem. Commun. 65, 1093-1108.  [ISI] [CrossRef] [ChemPort]
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tian, L., Sun, Y., Li, H., Zheng, X., Cheng, Y., Liu, X. & Qian, B. (2005). J. Inorg. Biochem. 99, 1646-1652.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]

Acta Cryst (2008). E64, o1843  [ doi:10.1107/S1600536808027311 ]

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