3-[(3-Oxo-1,3-dihydro­isobenzofuran-1-yl)amino]benzoic acid

Li, W.; Yin, H.; Wen, L.; Li, K.; Fan, W.

doi:10.1107/S1600536809038926

Volume 65
Part 10
Page o2579
October 2009

Received 18 September 2009
Accepted 25 September 2009
Online 30 September 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.107
Data-to-parameter ratio = 12.0
Details

3-[(3-Oxo-1,3-dihydroisobenzofuran-1-yl)amino]benzoic acid

Wenkuan Li,^a Handong Yin,^a ^* Liyuan Wen,^a Kang Li ^a and Weidong Fan ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
Correspondence e-mail: handongyin@163.com

In the title compound, C₁₅H₁₁NO₄, the dihedral angle formed by the benzene ring and isobenzofuran ring system is 67.82 (5) Å. The crystal structure is stabilized by intermolecular O-HO and N-HO hydrogen-bonding interactions.

Related literature

For general background to isobenzofuran derivatives, see: Landge et al. (2008); Paradkar et al. (1998); Joseph (1998). Odabasoglu & Büyükgüngör (2008).

Experimental

Crystal data

C₁₅H₁₁NO₄
M_r = 269.25
Monoclinic, P 2₁ /n
a = 10.9025 (15) Å
b = 8.1595 (12) Å
c = 14.2654 (18) Å
= 103.463 (1)°
V = 1234.2 (3) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 298 K
0.27 × 0.19 × 0.17 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.972, T_max = 0.982
6011 measured reflections
2171 independent reflections
1206 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.107
S = 0.90
2171 reflections
181 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.13 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1AO4ⁱ	0.82	1.91	2.712 (2)	166
N1-H1O2ⁱⁱ	0.86	2.16	2.956 (2)	154
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{5\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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: BQ2162 ).

Acknowledgements

We acknowledge the financial support of the Natural Science Foundation of China (No. 20771053) and the Natural Science Foundation of Shandong Province (Y2008B48). This work was also supported by the `Students Technology Cultural Innovation Fund' of Liaocheng University.

References

Joseph, A. R. (1998). J. Chem. Res. (S), pp. 332-333.
Landge, S. M., Berryman, M. & Törk, B. (2008). Tetrahedron Lett. 49, 4505-4508.
Odabasoglu, M. & Büyükgüngör, O. (2008). Acta Cryst. E64, o752-o753.
Paradkar, M. V., Ranade, A. A., Kulkarni, M. S., Godbole, H. M. & Joseph, A. R. (1998). J. Chem. Res. (S), pp. 332-333.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

organic compounds