2-[(E)-(5-tert-Butyl-2-hydroxy­phen­yl)­diazen­yl]benzoic acid

Basu Baul, T.S.; Paul, A.; Arman, H.D.; Tiekink, E.R.T.

doi:10.1107/S160053680803290X

Volume 64
Part 11
Page o2125
November 2008

Received 10 October 2008
Accepted 11 October 2008
Online 18 October 2008

Key indicators
Single-crystal X-ray study
T = 98 K
Mean (C-C) = 0.003 Å
R = 0.059
wR = 0.144
Data-to-parameter ratio = 15.0
Details

2-[(E)-(5-tert-Butyl-2-hydroxyphenyl)diazenyl]benzoic acid

Tushar S. Basu Baul,^a ⁺ Anup Paul,^a Hadi D. Arman ^b and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, North-Eastern Hill University, NEHU Permanent Campus, Umshing, Shillong 793 022, India, and ^bDepartment of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA
Correspondence e-mail: edward.tiekink@utsa.edu

The title compound, C₁₇H₁₈N₂O₃, is approximately planar, owing in part to an intramolecular bifurcated O-H(N,O) hydrogen bond; the dihedral angle between the two aromatic rings is 23.86 (9)°. In the crystal struture, centrosymmetrically related molecules associate into dimers via the eight-membered carboxylate {H-O-C=O}₂ synthon.

Related literature

For a related structure, see: Basu Baul et al. (2007). For background, see: Willem et al. (1998). For reviews of organotin carboxylates, see: Tiekink (1991).

Experimental

Crystal data

C₁₇H₁₈N₂O₃
M_r = 298.33
Monoclinic, P 2₁ /c
a = 5.9052 (19) Å
b = 10.872 (4) Å
c = 23.126 (8) Å
= 94.432 (4)°
V = 1480.3 (9) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 98 (2) K
0.35 × 0.16 × 0.08 mm

Data collection

Rigaku Saturn724 diffractometer
Absorption correction: none
8445 measured reflections
3068 independent reflections
2610 reflections with I > 2(I)
R_int = 0.065

Refinement

R[F² > 2(F²)] = 0.059
wR(F²) = 0.144
S = 1.12
3068 reflections
205 parameters
2 restraints
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3ON1	0.84	1.86	2.587 (2)	144
O3-H3OO1	0.84	2.26	2.894 (2)	132
O2-H2OO1ⁱ	0.84	1.86	2.687 (2)	170
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: CrystalClear (Rigaku Americas Corporation, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2500 ).

Acknowledgements

The financial support of the Department of Science and Technology, New Delhi, India (grant No. SR/S1/IC-03/2005 to TSBB), is gratefully acknowledged.

References

Basu Baul, T. S., Basu, S. & Tiekink, E. R. T. (2007). Acta Cryst. E63, o3358.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Rigaku Americas Corporation (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tiekink, E. R. T. (1991). Appl. Organomet. Chem. 5, 1-23.
Willem, R., Verbruggen, I., Gielen, M., Biesemans, M., Mahieu, B., Basu Baul, T. S. & Tiekink, E. R. T. (1998). Organometallics, 17, 5758-5766.

organic compounds