3-(2H-Benzotriazol-2-yl)-2-hydr­oxy-5-methyl­benzaldehyde

Li, C.-Y.; Tsai, C.-Y.; Lin, C.-H.; Ko, B.-T.

doi:10.1107/S1600536810007233

Volume 66
Part 4
Page o726
April 2010

Received 21 February 2010
Accepted 25 February 2010
Online 3 March 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.045
wR = 0.146
Data-to-parameter ratio = 17.1
Details

3-(2H-Benzotriazol-2-yl)-2-hydroxy-5-methylbenzaldehyde

Chen-Yu Li,^a Chen-Yen Tsai,^a Chia-Her Lin ^a and Bao-Tsan Ko ^a ^*

^aDepartment of Chemistry, Chung Yuan Christian University, Chung-Li 32023, Taiwan
Correspondence e-mail: btko@cycu.edu.tw

In the title compound, C₁₄H₁₁N₃O₂, the dihedral angle between the mean planes of the benzotriazole ring system and the benzene ring of the salicylaldehyde group is 2.4 (2)°. There is an intramolecular O-HN hydrogen bond which may influence the molecular conformation.

Related literature

For the application of N,N,O-tridentate Schiff-base metal complexes in the catalytic ring-opening polymerization of L-lactide, see: Wu et al. (2005); Chen et al. (2006). For a related structure, see: Li et al. (2009).

Experimental

Crystal data

C₁₄H₁₁N₃O₂
M_r = 253.26
Monoclinic, P 2₁ /c
a = 12.2724 (5) Å
b = 14.5018 (5) Å
c = 6.8897 (3) Å
= 91.571 (2)°
V = 1225.71 (8) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 296 K
0.34 × 0.31 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.972, T_max = 0.977
13912 measured reflections
2946 independent reflections
1657 reflections with I > 2(I)
R_int = 0.070

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.146
S = 1.01
2946 reflections
172 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1AN1	0.85	1.94	2.588 (2)	132

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5003 ).

Acknowledgements

We gratefully acknowledge the financial support in part from the National Science Council, Taiwan (NSC97-2113-M-033-005-MY2) and in part from the project of the specific research fields in Chung Yuan Christian University, Taiwan (No. CYCU-98-CR-CH).

References

Bruker (2008). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, H.-Y., Tang, H.-Y. & Lin, C.-C. (2006). Macromolecules, 39, 3745-3752.
Li, J.-Y., Liu, Y.-C., Lin, C.-H. & Ko, B.-T. (2009). Acta Cryst. E65, o2475.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wu, J.-C., Huang, B.-H., Hsueh, M.-L., Lai, S.-L. & Lin, C.-C. (2005). Polymer, 46, 9784-9792.

organic compounds