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Volume 69 
Part 9 
Pages m489-m490  
September 2013  

Received 16 July 2013
Accepted 7 August 2013
Online 10 August 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
R = 0.040
wR = 0.112
Data-to-parameter ratio = 15.2
Details
Open access

2-Amino-6-methylpyridinium trans-diaquadioxalatochromate(III) monohydrate

aLaboratoire de Matériaux et Cristallochimie, Département de Chimie, Faculté des Sciences, 2092 El Manar, Tunis, Tunisia
Correspondence e-mail: faouzi.zid@fst.rnu.tn

In the title compound, (C6H9N2)[Cr(C2O4)2(H2O)2]·H2O, the CrIII atom adopts a slightly distorted octahedral coordination environment defined by two chelating oxalate ligands in the equatorial plane and two water molecules in axial positions. A three-dimensional network is generated by intermolecular N-H...O and O-H...O hydrogen-bonding interactions involving the cation, the complex anion and the lattice water molecule.

Related literature

For general background to the coordination chemistry of oxalates, see: Martin et al. (2007[Martin, L., Day, P., Clegg, W., Harrington, R. W., Horton, P. N., Bingham, A., Hursthouse, M. B., McMillan, P. & Firth, S. (2007). J. Mater. Chem. 17, 3324-3329.]). For the structural characterization of organic-inorganic salts containing the [Cr(C2O4)2(H2O)2]- anion, see: Bélombé et al. (2009[Bélombé, M. M., Nenwa, J. & Emmerling, F. (2009). Z. Kristallogr. 224, 239-240.]); Nenwa et al. (2010[Nenwa, J., Belombe, M. M., Ngoune, J. & Fokwa, B. P. T. (2010). Acta Cryst. E66, m1410.]); Chérif et al. (2011[Chérif, I., Abdelhak, J., Zid, M. F. & Driss, A. (2011). Acta Cryst. E67, m1648-m1649.]); Chérif, Abdelhak et al. (2012[Chérif, I., Abdelhak, J., Zid, M. F. & Driss, A. (2012). Acta Cryst. E68, m824-m825.]); Chérif, Zid et al. (2012[Chérif, I., Zid, M. F., El-Ghozzi, M. & Avignant, D. (2012). Acta Cryst. E68, m900-m901.]). For C-O bond lengths in oxalate anions, see: Marinescu et al. (2000[Marinescu, G., Andruh, M., Lescouëzec, R., Munoz, M. C., Cano, J., Lloret, F. & Julve, M. (2000). New J. Chem. 24, 527-536.]). For geometric parameters of the 2-amino-6-methylpyridinium cation, see: Fun et al. (2008[Fun, H.-K., Jebas, S. R. & Sinthiya, A. (2008). Acta Cryst. E64, o697-o698.], 2009[Fun, H.-K., John, J., Jebas, S. R. & Balasubramanian, T. (2009). Acta Cryst. E65, o748-o749.], 2010[Fun, H.-K., Hemamalini, M. & Rajakannan, V. (2010). Acta Cryst. E66, o2108.]); Jebas et al. (2009[Jebas, S. R., Sinthiya, A., Ravindran Durai Nayagam, B., Schollmeyer, D. & Raj, S. A. C. (2009). Acta Cryst. E65, m521.]); Quah et al. (2008[Quah, C. K., Jebas, S. R. & Fun, H.-K. (2008). Acta Cryst. E64, o1878-o1879.]); Ramesh et al. (2010[Ramesh, P., Akalya, R., Chandramohan, A. & Ponnuswamy, M. N. (2010). Acta Cryst. E66, o1000.]); Rotondo et al. (2009[Rotondo, A., Bruno, G., Messina, F. & Nicoló, F. (2009). Acta Cryst. E65, m1203-m1204.]); Pan et al. (2008[Pan, Z.-C., Zhang, K.-L. & Ng, S. W. (2008). Acta Cryst. E64, m221.]). For discussion of hydrogen bonding, see: Blessing (1986[Blessing, R. H. (1986). Acta Cryst. B42, 613-621.]); Brown (1976[Brown, I. D. (1976). Acta Cryst. A32, 24-31.]).

[Scheme 1]

Experimental

Crystal data
  • (C6H9N2)[Cr(C2O4)2(H2O)2]·H2O

  • Mr = 391.24

  • Monoclinic, C 2/c

  • a = 18.572 (3) Å

  • b = 11.025 (2) Å

  • c = 14.975 (3) Å

  • [beta] = 96.28 (2)°

  • V = 3047.8 (10) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.81 mm-1

  • T = 298 K

  • 0.56 × 0.42 × 0.33 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.679, Tmax = 0.764

  • 4604 measured reflections

  • 3312 independent reflections

  • 2896 reflections with I > 2[sigma](I)

  • Rint = 0.037

  • 2 standard reflections every 120 min intensity decay: 3.2%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.112

  • S = 1.07

  • 3312 reflections

  • 218 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.65 e Å-3

  • [Delta][rho]min = -0.45 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H3...O7i 0.83 1.82 2.643 (2) 171
O1-H4...O10ii 0.83 1.87 2.681 (2) 165
O2-H2...O11iii 0.83 1.78 2.611 (2) 173
O2-H10...O8iv 0.83 1.85 2.675 (2) 172
N1-H7...O9v 0.93 1.90 2.829 (2) 174
N2-H5...O7vi 0.93 2.16 2.928 (3) 139
N2-H13...O10v 0.93 2.08 2.976 (3) 162
O11-H1...O8i 0.83 2.17 2.983 (2) 167
O11-H11...O6 0.83 2.03 2.845 (2) 169
Symmetry codes: (i) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]; (ii) [-x+1, y, -z+{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (v) x, y+1, z; (vi) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: CAD-4 EXPRESS (Duisenberg, 1992[Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96.]; Macícek & Yordanov, 1992[Macícek, J. & Yordanov, A. (1992). J. Appl. Cryst. 25, 73-80.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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, 1999[Brandenburg, K. & Putz, H. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); 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: MW2113 ).


References

Bélombé, M. M., Nenwa, J. & Emmerling, F. (2009). Z. Kristallogr. 224, 239-240.
Blessing, R. H. (1986). Acta Cryst. B42, 613-621.  [CSD] [CrossRef] [ISI] [details]
Brandenburg, K. & Putz, H. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Brown, I. D. (1976). Acta Cryst. A32, 24-31.  [CrossRef] [details]
Chérif, I., Abdelhak, J., Zid, M. F. & Driss, A. (2011). Acta Cryst. E67, m1648-m1649.  [CSD] [CrossRef] [details]
Chérif, I., Abdelhak, J., Zid, M. F. & Driss, A. (2012). Acta Cryst. E68, m824-m825.  [CSD] [CrossRef] [details]
Chérif, I., Zid, M. F., El-Ghozzi, M. & Avignant, D. (2012). Acta Cryst. E68, m900-m901.  [CSD] [CrossRef] [details]
Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96.  [CrossRef] [ChemPort] [ISI] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Fun, H.-K., Hemamalini, M. & Rajakannan, V. (2010). Acta Cryst. E66, o2108.  [CSD] [CrossRef] [details]
Fun, H.-K., Jebas, S. R. & Sinthiya, A. (2008). Acta Cryst. E64, o697-o698.  [CSD] [CrossRef] [ChemPort] [details]
Fun, H.-K., John, J., Jebas, S. R. & Balasubramanian, T. (2009). Acta Cryst. E65, o748-o749.  [CSD] [CrossRef] [ChemPort] [details]
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Jebas, S. R., Sinthiya, A., Ravindran Durai Nayagam, B., Schollmeyer, D. & Raj, S. A. C. (2009). Acta Cryst. E65, m521.  [CSD] [CrossRef] [details]
Macícek, J. & Yordanov, A. (1992). J. Appl. Cryst. 25, 73-80.  [CrossRef] [ISI] [details]
Marinescu, G., Andruh, M., Lescouëzec, R., Munoz, M. C., Cano, J., Lloret, F. & Julve, M. (2000). New J. Chem. 24, 527-536.  [ISI] [CSD] [CrossRef] [ChemPort]
Martin, L., Day, P., Clegg, W., Harrington, R. W., Horton, P. N., Bingham, A., Hursthouse, M. B., McMillan, P. & Firth, S. (2007). J. Mater. Chem. 17, 3324-3329.  [ISI] [CSD] [CrossRef] [ChemPort]
Nenwa, J., Belombe, M. M., Ngoune, J. & Fokwa, B. P. T. (2010). Acta Cryst. E66, m1410.  [CSD] [CrossRef] [details]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Pan, Z.-C., Zhang, K.-L. & Ng, S. W. (2008). Acta Cryst. E64, m221.  [CSD] [CrossRef] [details]
Quah, C. K., Jebas, S. R. & Fun, H.-K. (2008). Acta Cryst. E64, o1878-o1879.  [CSD] [CrossRef] [ChemPort] [details]
Ramesh, P., Akalya, R., Chandramohan, A. & Ponnuswamy, M. N. (2010). Acta Cryst. E66, o1000.  [CrossRef] [details]
Rotondo, A., Bruno, G., Messina, F. & Nicoló, F. (2009). Acta Cryst. E65, m1203-m1204.  [CSD] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, m489-m490   [ doi:10.1107/S1600536813022058 ]

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