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Volume 69 
Part 9 
Page o1388  
September 2013  

Received 17 June 2013
Accepted 28 July 2013
Online 7 August 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.117
Data-to-parameter ratio = 14.1
Details
Open access

1,2-Ethylenediaminium bis(2-benzamidobenzoate)

aInstitute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, M. Ulugbek Str. 83, Tashkent 100125, Uzbekistan
Correspondence e-mail: kimyogar8221@mail.ru

In the title salt, C2H10N22+·2C14H10NO3-, the ethylenediaminium dication lies on an inversion centre. In the anion, the benzene rings make a dihedral angle of 33.87 (9)° and intramolecular N-H...O and C-H...O hydrogen bonds occur. All the amino H atoms are involved in N-H...O hydrogen bonds. These hydrogen bonds link the ionic units into a three-dimensional network. In addition, the crystal structure also features weak C-H...O interactions.

Related literature

For the crystal structure of 1,2-ethylenediammonium salts of aromatic acids, see: Shen-Tu et al. (2008[Shen-Tu, C., Ma, L.-L., Xu, W., Chen, Y. & Jin, Z.-M. (2008). Acta Cryst. E64, o346.]); Zhao & Feng (2011[Zhao, L. & Feng, L. (2011). Acta Cryst. E67, o1789.]). For the crystal structure of the 2-benzamidobenzoyl acid CuII coordination compound, see: Kaizer et al. (2006[Kaizer, J., Csay, T., Speier, G., Reglier, M. & Giorgi, M. (2006). Inorg. Chem. Commun. 9, 1037-1039.]).

[Scheme 1]

Experimental

Crystal data
  • 0.5C2H10N22+·C14H10NO3-

  • Mr = 271.29

  • Monoclinic, P 21 /n

  • a = 5.314 (1) Å

  • b = 13.745 (2) Å

  • c = 18.580 (4) Å

  • [beta] = 93.66 (2)°

  • V = 1354.3 (4) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.77 mm-1

  • T = 293 K

  • 0.6 × 0.3 × 0.2 mm

Data collection
  • Oxford Diffraction Xcalibur Ruby diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.699, Tmax = 1.000

  • 5702 measured reflections

  • 2772 independent reflections

  • 1851 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.117

  • S = 0.95

  • 2772 reflections

  • 197 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O2 0.90 (2) 1.81 (2) 2.608 (2) 146.8 (19)
N1s-H1A...O1 0.94 (2) 1.89 (2) 2.807 (2) 165 (2)
N1s-H1B...O3i 0.98 (2) 1.76 (2) 2.729 (2) 170 (2)
N1s-H1C...O2ii 0.94 (2) 1.84 (2) 2.753 (2) 163 (2)
C2s-H2B...O3iii 0.97 2.59 3.315 (2) 131
C6-H6...O3iii 0.93 2.50 3.319 (2) 147
C9-H9...O1 0.93 2.25 2.863 (2) 123
Symmetry codes: (i) [-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2204 ).


Acknowledgements

This work was supported by a Grant for Fundamental Research from the Center of Science and Technology, Uzbekistan (No. FA-F3-T-141).

References

Kaizer, J., Csay, T., Speier, G., Reglier, M. & Giorgi, M. (2006). Inorg. Chem. Commun. 9, 1037-1039.  [ISI] [CSD] [CrossRef] [ChemPort]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Shen-Tu, C., Ma, L.-L., Xu, W., Chen, Y. & Jin, Z.-M. (2008). Acta Cryst. E64, o346.  [CSD] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zhao, L. & Feng, L. (2011). Acta Cryst. E67, o1789.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o1388  [ doi:10.1107/S1600536813021028 ]

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