3-Carb­oxy­methyl-1H-indole-4-carb­oxy­lic acid

Mao, S.

doi:10.1107/S1600536811051865

Volume 68
Part 1
Page o146
January 2012

Received 29 November 2011
Accepted 1 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.046
wR = 0.132
Data-to-parameter ratio = 15.2
Details

3-Carboxymethyl-1H-indole-4-carboxylic acid

Shulin Mao ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
Correspondence e-mail: chmsunbw@seu.edu.cn

In the title compound, C₁₁H₉NO₄, the carboxyl group bonded to the six-membered ring lies close to the plane of the 1H-indole ring system [dihedral angle = 13.13 (9)°], whereas the carboxylic acid group linked to the five-membered ring by a methylene bridge is close to perpendicular [78.85 (9)°]. In the crystal, O-HO and N-HO hydrogen bonds link the molecules, generating (110) sheets.

Related literature

For background to indoles as pharmaceuticals, see: Lang et al. (2011).

Experimental

Crystal data

C₁₁H₉NO₄
M_r = 219.19
Triclinic, $[P \overline 1]$
a = 5.4573 (11) Å
b = 9.823 (2) Å
c = 9.940 (2) Å
= 73.90 (3)°
= 78.57 (3)°
= 80.40 (3)°
V = 498.3 (2) Å³
Z = 2
Mo K radiation
= 0.11 mm^-1
T = 293 K
0.30 × 0.23 × 0.20 mm

Data collection

Rigaku SCXmini CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.977, T_max = 0.984
5115 measured reflections
2263 independent reflections
1786 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.132
S = 0.95
2239 reflections
147 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2ⁱ	0.82	1.83	2.6504 (19)	174
O4-H4O3ⁱⁱ	0.82	1.91	2.719 (2)	171
N1-H1BO3ⁱⁱⁱ	0.86	2.38	3.152 (2)	150
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x, -y+2, -z+2; (iii) -x+1, -y+1, -z+2.

Data collection: CrystalClear (Rigaku, 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: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6541 ).

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Lang, L., Wu, J.-L., Shi, L.-J., Xia, C.-G. & Li, F.-W. (2011). Chem. Commun. 47, 12553-12555.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds