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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 [sigma](C-C) = 0.002 Å
R = 0.046
wR = 0.132
Data-to-parameter ratio = 15.2
Details
Open access

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

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-H...O and N-H...O hydrogen bonds link the molecules, generating (110) sheets.

Related literature

For background to indoles as pharmaceuticals, see: Lang et al. (2011[Lang, L., Wu, J.-L., Shi, L.-J., Xia, C.-G. & Li, F.-W. (2011). Chem. Commun. 47, 12553-12555.]).

[Scheme 1]

Experimental

Crystal data
  • C11H9NO4

  • Mr = 219.19

  • Triclinic, [P \overline 1]

  • a = 5.4573 (11) Å

  • b = 9.823 (2) Å

  • c = 9.940 (2) Å

  • [alpha] = 73.90 (3)°

  • [beta] = 78.57 (3)°

  • [gamma] = 80.40 (3)°

  • V = 498.3 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.977, Tmax = 0.984

  • 5115 measured reflections

  • 2263 independent reflections

  • 1786 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.132

  • S = 0.95

  • 2239 reflections

  • 147 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2i 0.82 1.83 2.6504 (19) 174
O4-H4...O3ii 0.82 1.91 2.719 (2) 171
N1-H1B...O3iii 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[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); 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.  [CSD] [CrossRef] [ChemPort]
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o146  [ doi:10.1107/S1600536811051865 ]

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