4-(4-Hy­droxy­methyl-1H-1,2,3-triazol-1-yl)benzoic acid

Ishak, D.H.A.; Tajuddin, H.A.; Abdullah, Z.; Abd Halim, S.N.; Tiekink, E.R.T.

doi:10.1107/S1600536811022409

Volume 67
Part 7
Page o1658
July 2011

Received 7 June 2011
Accepted 9 June 2011
Online 18 June 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.040
wR = 0.130
Data-to-parameter ratio = 13.9
Details

4-(4-Hydroxymethyl-1H-1,2,3-triazol-1-yl)benzoic acid

Dayang Hazwani Abang Ishak,^a Hairul Anuar Tajuddin,^a ⁺ Zanariah Abdullah,^a Siti Nadiah Abd Halim ^a and Edward R. T. Tiekink ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

In the title compound, C₁₀H₉N₃O₃, there is a small twist between the benzene and triazole rings [dihedral angle = 6.32 (7)°]; the carboxylic acid residue is almost coplanar with the benzene ring to which it is attached [O-C-C-C torsion angle = 1.49 (19)°]. The main deviation from coplanarity of the non-H atoms is found for the hydroxy group which is almost perpendicular to the remaining atoms [N-C-C-O torsion angle = -75.46 (16)°]. In the crystal, the presence of O-HO (between carboxyl groups) and O-HN (between the hydroxy group and the triazole ring) hydrogen bonds leads to supramolecular chains along [03 $[\overline{1}]$ ]. The chains are connected into sheets via C-HO(hydroxy) interactions.

Related literature

For background to the fluorescence potential, see: McCaroll & Wandruzska (1997). For synthetic protocols, see: Rostovtsev et al. (2002); Ryu & Zhao (2005); Himo et al. (2005). For additional geometric analysis, see: Spek (2009).

Experimental

Crystal data

C₁₀H₉N₃O₃
M_r = 219.20
Triclinic, $[P \overline 1]$
a = 5.4641 (7) Å
b = 6.6596 (8) Å
c = 13.1898 (16) Å
= 88.828 (2)°
= 83.577 (2)°
= 75.828 (2)°
V = 462.42 (10) Å³
Z = 2
Mo K radiation
= 0.12 mm^-1
T = 100 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.684, T_max = 0.746
5837 measured reflections
2099 independent reflections
1852 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.130
S = 1.08
2099 reflections
151 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.30 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1oO2ⁱ	0.85 (1)	1.77 (2)	2.6119 (14)	173 (2)
O3-H3oN3ⁱⁱ	0.85 (1)	1.96 (1)	2.7995 (16)	169 (2)
C6-H6O3ⁱⁱⁱ	0.95	2.60	3.5309 (19)	167
C8-H8O3ⁱⁱⁱ	0.95	2.23	3.1262 (18)	158
Symmetry codes: (i) -x, -y-1, -z+1; (ii) -x, -y+2, -z; (iii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5906 ).

Acknowledgements

The University of Malaya is thanked for a University of Malaya Research Grant (No. RG080/09AFR) and for support of the crystallographic facility.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Himo, F., Lovell, T., Hilgraf, R., Rostovtsev, V. V., Noodleman, L., Sharpless, K. B. & Fokin, V. V. (2005). J. Am. Chem. Soc. 127, 210-216.
McCaroll, M. E. & Wandruzska, R. V. (1997). J. Fluoresc. 7, 185-193.
Rostovtsev, V. V., Green, L. G., Fokin, V. V. & Sharpless, K. B. (2002). Angew. Chem. Int. Ed. 41, 2596-2699.
Ryu, E. H. & Zhao, Y. (2005). Org. Lett. 7, 1035-1037.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds