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Volume 69 
Part 11 
Pages o1639-o1640  
November 2013  

Received 22 September 2013
Accepted 9 October 2013
Online 16 October 2013

Key indicators
Single-crystal X-ray study
T = 290 K
Mean [sigma](N-C) = 0.001 Å
R = 0.030
wR = 0.065
Data-to-parameter ratio = 35.6
Details
Open access

(Di­methyl­phosphor­yl)methanaminium nitrate

aInstitut für Anorganische Chemie und Strukturchemie, Lehrstuhl II: Material- und Strukturforschung, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, D-40225 Düsseldorf, Germany
Correspondence e-mail: reissg@hhu.de

In the crystal of the title salt, C3H11NOP+·NO3-, dicationic inversion dimers are head-to-tail connected by a pair of strong N-H...O hydrogen bonds. The resulting graph-set descriptor of this ring system is R22(10). The nitrate counter-anions connect the dicationic dimers via N-H...O hydrogen bonds, forming two-dimensional networks in the bc plane.

Related literature

For transition metal complexes of the (dimethylphos­phor­yl)methanamine (dpma) ligand, see: Dodoff et al. (1990[Dodoff, N., Macicek, J., Angelova, O., Varbanov, S. G. & Spassovska, N. (1990). J. Coord. Chem. 22, 219-228.]); Borisov et al. (1994[Borisov, G., Varbanov, S. G., Venanzi, L. M., Albinati, A. & Demartin, F. (1994). Inorg. Chem. 33, 5430-5437.]); Trendafilova et al. (1997[Trendafilova, N., Georgieva, I., Bauer, G., Varbanov, S. G. & Dodoff, N. (1997). Spectrochim. Acta Part A, 53, 819-828.]); Kochel (2009[Kochel, A. (2009). Inorg. Chim. Acta, 362, 1379-1382.]). For transition metal complexes of the protonated dpmaH+ ligand, see: Reiss (2013a[Reiss, G. J. (2013a). Acta Cryst. E69, m248-m249.],b[Reiss, G. J. (2013b). Acta Cryst. E69, m250-m251.]). For simple dpmaH+ salts, see: Reiss & Jörgens (2012[Reiss, G. J. & Jörgens, S. (2012). Acta Cryst. E68, o2899-o2900.]); Lambertz et al. (2013[Lambertz, C., Luppa, A. & Reiss, G. J. (2013). Z. Kristallogr. New Cryst. Struct. 228, 227-228.]); Buhl et al. (2013[Buhl, D., Gün, H., Jablonka, A. & Reiss, G. J. (2013). Crystals, 3, 350-362.]); Reiss (2013c[Reiss, G. J. (2013c). Acta Cryst. E69, o1253-o1254.],d[Reiss, G. J. (2013d). Z. Kristallogr. New Cryst. Struct. 228, 431-433.]). For a definition of the term tecton, see: Brunet et al. (1997[Brunet, P., Simard, M. & Wuest, J. D. (1997). J. Am. Chem. Soc. 119, 2737-2738.]). For a definition of the term anti­type, see: Lima-de-Faria et al. (1990[Lima-de-Faria, J., Hellner, E., Liebau, F., Makovicky, E. & Parthé, E. (1990). Acta Cryst. A46, 1-11.]). For graph-set theory, see: Etter et al.(1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Grell et al. (2002[Grell, J., Bernstein, J. & Tinhofer, G. (2002). Crystallogr. Rev. 8, 1-56.]). For structures showing an analogous topology, see: Holl & Thewalt (1986[Holl, K. & Thewalt, U. (1986). Z. Naturforsch. Teil B, 41, 581-586.]); Reiss (2002[Reiß, G. J. (2002). Acta Cryst. E58, m47-m50.]); Reiss & Helmbrecht (2012[Reiss, G. J. & Helmbrecht, C. (2012). Acta Cryst. E68, m1402-m1403.]).

[Scheme 1]

Experimental

Crystal data
  • C3H11NOP+·NO3-

  • Mr = 170.11

  • Monoclinic, P 21 /c

  • a = 8.7718 (3) Å

  • b = 7.9892 (3) Å

  • c = 11.2921 (6) Å

  • [beta] = 96.581 (4)°

  • V = 786.14 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.32 mm-1

  • T = 290 K

  • 0.63 × 0.38 × 0.19 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.809, Tmax = 1.000

  • 82785 measured reflections

  • 3770 independent reflections

  • 3313 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.065

  • S = 1.01

  • 3770 reflections

  • 106 parameters

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

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H11...O2 0.894 (14) 1.966 (15) 2.8555 (11) 173.1 (12)
N1-H12...O3i 0.902 (14) 1.979 (14) 2.8784 (12) 174.5 (13)
N1-H13...O1ii 0.874 (14) 1.888 (14) 2.7493 (10) 168.2 (13)
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) -x, -y+1, -z.

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: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013; molecular graphics: DIAMOND (Brandenburg, 2012[Brandenburg, K. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); 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: LH5656 ).


Acknowledgements

We thank E. Hammes for technical support. Furthermore, the funding by the 'Lehrförderfond' of the Heinrich-Heine-Universität Düsseldorf is gratefully acknowledged.

References

Borisov, G., Varbanov, S. G., Venanzi, L. M., Albinati, A. & Demartin, F. (1994). Inorg. Chem. 33, 5430-5437.  [CSD] [CrossRef] [ChemPort] [Web of Science]
Brandenburg, K. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Brunet, P., Simard, M. & Wuest, J. D. (1997). J. Am. Chem. Soc. 119, 2737-2738.  [CSD] [CrossRef] [ChemPort] [Web of Science]
Buhl, D., Gün, H., Jablonka, A. & Reiss, G. J. (2013). Crystals, 3, 350-362.  [CrossRef] [ChemPort]
Dodoff, N., Macicek, J., Angelova, O., Varbanov, S. G. & Spassovska, N. (1990). J. Coord. Chem. 22, 219-228.  [CrossRef] [ChemPort]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [Web of Science] [IUCr Journals]
Grell, J., Bernstein, J. & Tinhofer, G. (2002). Crystallogr. Rev. 8, 1-56.  [CrossRef] [ChemPort]
Holl, K. & Thewalt, U. (1986). Z. Naturforsch. Teil B, 41, 581-586.
Kochel, A. (2009). Inorg. Chim. Acta, 362, 1379-1382.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Lambertz, C., Luppa, A. & Reiss, G. J. (2013). Z. Kristallogr. New Cryst. Struct. 228, 227-228.  [ChemPort]
Lima-de-Faria, J., Hellner, E., Liebau, F., Makovicky, E. & Parthé, E. (1990). Acta Cryst. A46, 1-11.  [CrossRef] [IUCr Journals]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Reiß, G. J. (2002). Acta Cryst. E58, m47-m50.  [CSD] [CrossRef] [IUCr Journals]
Reiss, G. J. (2013a). Acta Cryst. E69, m248-m249.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Reiss, G. J. (2013b). Acta Cryst. E69, m250-m251.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Reiss, G. J. (2013c). Acta Cryst. E69, o1253-o1254.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Reiss, G. J. (2013d). Z. Kristallogr. New Cryst. Struct. 228, 431-433.
Reiss, G. J. & Helmbrecht, C. (2012). Acta Cryst. E68, m1402-m1403.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Reiss, G. J. & Jörgens, S. (2012). Acta Cryst. E68, o2899-o2900.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Trendafilova, N., Georgieva, I., Bauer, G., Varbanov, S. G. & Dodoff, N. (1997). Spectrochim. Acta Part A, 53, 819-828.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1639-o1640   [ doi:10.1107/S1600536813027694 ]

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