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Volume 69 
Part 11 
Pages o1643-o1644  
November 2013  

Received 13 September 2013
Accepted 7 October 2013
Online 16 October 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.012 Å
R = 0.061
wR = 0.180
Data-to-parameter ratio = 8.9
Details
Open access

N,N'-Bis(2-amino­benz­yl)ethane-1,2-diaminium dinitrate

aUniversidad Regiomontana A.C., 15 de Mayo 567 Pte., Monterrey, Nuevo León CP 64000, Mexico, and bUniversidad Autónoma de Nuevo León, UANL, Facultad de Ciencias Químicas, Av. Universidad S/N, Ciudad Universitaria, San Nicolás de los Garza, Nuevo León CP 66451, Mexico
Correspondence e-mail: sylvain_bernes@Hotmail.com

In the title salt, C16H24N42+·2NO3-, both the cation and anion are placed in general positions, although the cation displays non-crystallographic inversion symmetry, with the aliphatic chain extended in an all-trans conformation. The benzene rings are almost parallel, with a dihedral angle between their mean planes of 3.3 (6)°. The nitrate ions are placed in the vicinity of the protonated amine groups, forming efficient N-H...O inter-ion hydrogen bonds. Each nitrate ion in the asymmetric unit bridges two symmetry-related cations, forming an R44(18) ring, a common motif in organic ammonium nitrate salts. This results in the formation of chains along [010] with alternating cations and anions. The neutral amine groups are involved in slightly weaker N-H...O hydrogen bonds with the nitrate O atoms, and there are also a number of C-H...O hydrogen bonds present. The resulting supra­molecular structure is based on a two-dimensional network extending in the ab plane.

Related literature

For the structure of the free neutral amine, see: Rodríguez de Barbarín et al. (2007[Rodríguez de Barbarín, C., Bernès, S., Nájera, B., Elizondo, P. & Cerda, P. (2007). Acta Cryst. E63, o549-o550.]). For the p-toluene­sulfonate salt of the title cation, see: Garza Rodríguez et al. (2011[Garza Rodríguez, L. Á., Bernès, S., Elizondo Martínez, P., Nájera Martínez, B. & Rodríguez de Luna, S. L. (2011). Acta Cryst. E67, o3235-o3236.]). For related di­ammonium nitrate salts featuring R44(18) motifs, see: Liu et al. (2007[Liu, Y.-F., Xia, H.-T., Wang, D.-Q., Yang, S.-P. & Meng, Y.-L. (2007). Acta Cryst. E63, o3836.]); Yang et al. (2007[Yang, S.-P., Han, L.-J., Wang, D.-Q. & Xia, H.-T. (2007). Acta Cryst. E63, o3880.]). For supra­molecular motifs nomenclature, see: Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]). For the synthesis of the title salt, see: Garza Rodríguez (2010[Garza Rodríguez, L. Á. (2010). PhD thesis, Universidad Autónoma de Nuevo León, Mexico.]).

[Scheme 1]

Experimental

Crystal data
  • C16H24N42+·2NO3-

  • Mr = 396.41

  • Orthorhombic, P n a 21

  • a = 11.041 (5) Å

  • b = 5.760 (4) Å

  • c = 30.069 (13) Å

  • V = 1912.1 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 298 K

  • 0.60 × 0.20 × 0.20 mm

Data collection
  • Siemens P4 diffractometer

  • 4371 measured reflections

  • 2473 independent reflections

  • 1501 reflections with I > 2[sigma](I)

  • Rint = 0.053

  • 3 standard reflections every 97 reflections intensity decay: 1.5%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.061

  • wR(F2) = 0.180

  • S = 1.61

  • 2473 reflections

  • 278 parameters

  • 13 restraints

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

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N9-H9A...O23i 0.94 (4) 1.87 (3) 2.794 (8) 167 (7)
N9-H9B...O24 0.95 (5) 1.96 (5) 2.879 (7) 164 (5)
N12-H12A...O27 0.92 (3) 1.88 (3) 2.787 (8) 168 (8)
N12-H12B...O28i 0.91 (5) 1.95 (5) 2.862 (8) 176 (9)
N1-H1B...O22ii 0.90 (7) 2.55 (8) 3.290 (11) 141 (9)
N1-H1B...O24ii 0.90 (7) 2.40 (7) 3.272 (10) 166 (9)
N9-H9A...O22i 0.94 (4) 2.38 (6) 3.050 (8) 128 (5)
N12-H12A...O26 0.92 (3) 2.36 (5) 3.046 (8) 132 (4)
N12-H12B...O27i 0.91 (5) 2.49 (5) 3.096 (8) 125 (4)
N20-H20B...O26iii 0.91 (7) 2.56 (8) 3.246 (12) 133 (8)
N20-H20B...O28iii 0.91 (7) 2.32 (8) 3.204 (11) 165 (8)
C8-H8B...O24ii 0.97 2.46 3.327 (9) 149
C10-H10A...O24ii 0.97 2.41 3.258 (8) 145
C10-H10B...O22iv 0.97 2.58 3.291 (9) 130
C11-H11A...O27i 0.97 2.56 3.147 (9) 119
C11-H11A...O26v 0.97 2.57 3.285 (9) 131
C11-H11B...O28iii 0.97 2.41 3.249 (9) 145
C13-H13A...O28iii 0.97 2.46 3.315 (10) 147
Symmetry codes: (i) x, y+1, z; (ii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z]; (iii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]; (iv) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]; (v) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z].

Data collection: XSCANS (Siemens, 1996[Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL2013.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2415 ).


Acknowledgements

The authors thank the FCQ-UANL (project No. 03-6375-QMT-08-005) and PAICyT (Project No. IT164-09) for financial support. LAGR acknowledges a grant from the CONACyT program "Dirección de Tesis entre la UANL y la University of Texas at Austin y/o Instituciones de Educación Superior de la ANUIES" (grant N.L.-2006-C09 32658).

References

Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [Web of Science]
Garza Rodríguez, L. Á. (2010). PhD thesis, Universidad Autónoma de Nuevo León, Mexico.
Garza Rodríguez, L. Á., Bernès, S., Elizondo Martínez, P., Nájera Martínez, B. & Rodríguez de Luna, S. L. (2011). Acta Cryst. E67, o3235-o3236.  [CSD] [CrossRef] [IUCr Journals]
Liu, Y.-F., Xia, H.-T., Wang, D.-Q., Yang, S.-P. & Meng, Y.-L. (2007). Acta Cryst. E63, o3836.  [CSD] [CrossRef] [IUCr Journals]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Rodríguez de Barbarín, C., Bernès, S., Nájera, B., Elizondo, P. & Cerda, P. (2007). Acta Cryst. E63, o549-o550.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Yang, S.-P., Han, L.-J., Wang, D.-Q. & Xia, H.-T. (2007). Acta Cryst. E63, o3880.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1643-o1644   [ doi:10.1107/S1600536813027475 ]

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