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Volume 69 
Part 7 
Pages o1152-o1153  
July 2013  

Received 13 June 2013
Accepted 19 June 2013
Online 26 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.036
wR = 0.100
Data-to-parameter ratio = 12.3
Details
Open access

N,N'-Dihydroxybenzene-1,2:4,5-tetracarboximide dihydrate

aDipartimento di Scienze Chimiche, Università degli Studi di Napoli 'Federico II', Complesso di Monte S. Angelo, Via Cinthia, 80126 Napoli, Italy
Correspondence e-mail: roberto.centore@unina.it

In the title compound, C10H4N2O6·2H2O, the organic molecule has crystallographically imposed inversion symmetry. The atoms of the three fused rings of the molecule are coplanar within 0.0246 (8) Å, while the two hydroxy O atoms are displaced from the mean plane of the molecule by 0.127 (1) Å. In the crystal, infinite near-planar layers of close-packed molecules are formed by hydrogen bonding between water O-H donor groups and carbonyl O-atom acceptors, and by weak interactions between C-H donor groups and water O-atom acceptors. The layers are parallel to the {102} family of planes. The stacked planes are held together by hydrogen bonding between N-OH donor groups and water O-atom acceptors.

Related literature

For semiconductor, optoelectronic and piezoelectric materials containing heterocycles, see: Centore, Ricciotti et al. (2012[Centore, R., Ricciotti, L., Carella, A., Roviello, A., Causà, M., Barra, M., Ciccullo, F. & Cassinese, A. (2012). Org. Electron. 13, 2083-2093.]); Centore, Concilio et al. (2012[Centore, R., Concilio, A., Borbone, F., Fusco, S., Carella, A., Roviello, A., Stracci, G. & Gianvito, A. (2012). J. Polym. Sci. Part B Polym. Phys. 50, 650-655.]). For the structural analysis of conjugation in organic molecules containing heterocycles, see: Carella et al. (2004[Carella, A., Centore, R., Fort, A., Peluso, A., Sirigu, A. & Tuzi, A. (2004). Eur. J. Org. Chem. pp. 2620-2626.]). For the crystal packing of heterocycles containing nitrogen, see: Centore et al. (2013a[Centore, R., Piccialli, V. & Tuzi, A. (2013a). Acta Cryst. E69, o667-o668.],b[Centore, R., Piccialli, V. & Tuzi, A. (2013b). Acta Cryst. E69, o802-o803.]). For the crystal engineering of structures containing stacked infinite planar layers, see: Centore, Causà et al. (2013[Centore, R., Causà, M., Fusco, S. & Carella, A. (2013). Cryst. Growth Des. In the press. doi:10.1021/cg400750d.]). For the principle of close packing in organic crystallography, see: Kitaigorodskii (1961[Kitaigorodskii, A. I. (1961). In Organic Chemical Crystallography. New York: Consultants Bureau.]).

[Scheme 1]

Experimental

Crystal data
  • C10H4N2O6·2H2O

  • Mr = 284.18

  • Monoclinic, P 21 /c

  • a = 6.874 (3) Å

  • b = 10.189 (5) Å

  • c = 8.099 (4) Å

  • [beta] = 106.58 (2)°

  • V = 543.7 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.15 mm-1

  • T = 293 K

  • 0.40 × 0.40 × 0.30 mm

Data collection
  • Bruker-Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.941, Tmax = 0.955

  • 4484 measured reflections

  • 1231 independent reflections

  • 1100 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.100

  • S = 1.09

  • 1231 reflections

  • 100 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3...O4i 0.886 (19) 1.768 (19) 2.6516 (18) 175.2 (17)
O4-H4A...O2ii 0.896 (19) 2.15 (2) 3.0441 (17) 172.4 (16)
O4-H4B...O1iii 0.909 (19) 1.990 (19) 2.8879 (16) 169.3 (15)
C1-H1...O4 0.93 2.40 3.280 (2) 158
Symmetry codes: (i) x-1, y, z; (ii) -x, -y+1, -z; (iii) [x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 1999[Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000[Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893-898.]); data reduction: EVALCCD (Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5073 ).


Acknowledgements

The authors thank the Centro Interdipartimentale di Metodologie Chimico-Fisiche, Università degli Studi di Napoli `Federico II'.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Carella, A., Centore, R., Fort, A., Peluso, A., Sirigu, A. & Tuzi, A. (2004). Eur. J. Org. Chem. pp. 2620-2626.  [CSD] [CrossRef]
Centore, R., Causà, M., Fusco, S. & Carella, A. (2013). Cryst. Growth Des. In the press. doi:10.1021/cg400750d.
Centore, R., Concilio, A., Borbone, F., Fusco, S., Carella, A., Roviello, A., Stracci, G. & Gianvito, A. (2012). J. Polym. Sci. Part B Polym. Phys. 50, 650-655.  [Web of Science] [CrossRef] [ChemPort]
Centore, R., Piccialli, V. & Tuzi, A. (2013a). Acta Cryst. E69, o667-o668.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Centore, R., Piccialli, V. & Tuzi, A. (2013b). Acta Cryst. E69, o802-o803.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Centore, R., Ricciotti, L., Carella, A., Roviello, A., Causà, M., Barra, M., Ciccullo, F. & Cassinese, A. (2012). Org. Electron. 13, 2083-2093.  [Web of Science] [CrossRef] [ChemPort]
Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893-898.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Kitaigorodskii, A. I. (1961). In Organic Chemical Crystallography. New York: Consultants Bureau.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1152-o1153   [ doi:10.1107/S1600536813016991 ]

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