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Volume 68 
Part 1 
Page o206  
January 2012  

Received 30 November 2011
Accepted 14 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.009 Å
R = 0.092
wR = 0.308
Data-to-parameter ratio = 14.3
Details
Open access

4-Nitroisophthalic acid

aKey Laboratory of Urban and Architectural Heritage Conservation, (Southeast University), Ministry of Education, Nanjing 210096, People's Republic of China, and College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
Correspondence e-mail: peluoyh@sina.com

In the crystal structure of the title compound, C8H5NO6, both carboxyl groups are involved in intermolecular centrosymmetric cyclic O-H...O hydrogen-bonding associations, which give a zigzag chain structure extending along (2[\overline{1}]1). Weak [pi]-[pi] stacking interactions are also present [minimum ring centroid separation = 3.893 (4) Å].

Related literature

For 4-nitroisophthalic acid as an intermediate in the synthesis of pharmaceutical drugs and as a ligand in transition metal complexes, see: Birk & Weihe (2009[Birk, T. & Weihe, H. (2009). J. Chem. Crystallogr. 39, 766-771.]); Pan et al. (2011[Pan, M.-L., Luo, Y.-H. & Mao, S.-L. (2011). Acta Cryst. E67, o2345.]).

[Scheme 1]

Experimental

Crystal data
  • C8H5NO6

  • Mr = 211.13

  • Triclinic, [P \overline 1]

  • a = 7.0261 (14) Å

  • b = 7.4380 (15) Å

  • c = 8.5775 (17) Å

  • [alpha] = 80.09 (3)°

  • [beta] = 86.22 (3)°

  • [gamma] = 75.37 (3)°

  • V = 427.14 (15) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.15 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Rigaku SCXmini CCD-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.957, Tmax = 0.971

  • 4103 measured reflections

  • 1943 independent reflections

  • 1554 reflections with I > 2[sigma](I)

  • Rint = 0.136

Refinement
  • R[F2 > 2[sigma](F2)] = 0.092

  • wR(F2) = 0.308

  • S = 0.86

  • 1943 reflections

  • 136 parameters

  • 8 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.50 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H4...O3i 0.86 1.76 2.605 (7) 168
O5-H5...O6ii 0.87 1.73 2.602 (7) 180
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x, -y+2, -z.

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: ZS2171 ).


References

Birk, T. & Weihe, H. (2009). J. Chem. Crystallogr. 39, 766-771.  [ISI] [CSD] [CrossRef] [ChemPort]
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Pan, M.-L., Luo, Y.-H. & Mao, S.-L. (2011). Acta Cryst. E67, o2345.  [CSD] [CrossRef] [details]
Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o206  [ doi:10.1107/S1600536811053797 ]

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