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Volume 69 
Part 8 
Pages o1253-o1254  
August 2013  

Received 7 July 2013
Accepted 9 July 2013
Online 13 July 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](N-C) = 0.005 Å
R = 0.016
wR = 0.033
Data-to-parameter ratio = 21.1
Details
Open access

(Dimethylphosphoryl)methanaminium iodide-(dimethylphosphoryl)methanamine (1/1)

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

The asymmetric unit of the title structure, C3H11NOP+·I-·C3H10NOP, consists of one (dimethylphosphoryl)methanamine (dpma) molecule, one (dimethylphosphoryl)methanaminium (dpmaH) ion and one iodide counter-anion. In the crystal, medium-strong to weak N-H...O and N-H...N hydrogen bonds connect dpmaH cations and dpma molecules into strands along [001]. The iodide counter-anions form only very weak hydrogen bonds. The crystal used for the diffraction study was found to be an inversion twin with a ratio of 0.83 (2):0.17 (2). The title structure is isotypic to that of dpmaH[ClO4dpma [Buhl et al. (2013[Buhl, D., Gün, H., Jablonka, A. & Reiss, G. J. (2013). Crystals 3, 350-362.]). Crystals 3, 350-362].

Related literature

For transition metal complexes of the 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, A53, 819-828.]); Kochel (2009[Kochel, A. (2009). Inorg. Chim. Acta, 362, 1379-1382.]). For transition metal complexes of the cationic 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 dpmaH+ salts, see: Reiss & Jörgens (2012[Reiss, G. J. & Jörgens, S. (2012). Acta Cryst. E68, o2899-o2900.]); Buhl et al. (2013[Buhl, D., Gün, H., Jablonka, A. & Reiss, G. J. (2013). Crystals 3, 350-362.]); Lambertz et al. (2013[Lambertz, C., Luppa, A. & Reiss, G. J. (2013). Z. Kristallogr. New Cryst. Struct. 228, 227-228.]). For the term tecton, see: Brunet et al. (1997[Brunet, P., Simard, M. & Wuest, J. D. (1997). J. Am. Chem. Soc. 119, 2737-2738.]). For the graph-set analysis method, see: Grell et al. (2002[Grell, J., Bernstein, J. & Tinhofer, G. (2002). Crystallogr. Rev. 8, 1-56.]).

[Scheme 1]

Experimental

Crystal data
  • C3H11NOP+·I-·C3H10NOP

  • Mr = 342.09

  • Orthorhombic, P c a 21

  • a = 17.7791 (3) Å

  • b = 11.1766 (2) Å

  • c = 6.91805 (12) Å

  • V = 1374.69 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.54 mm-1

  • T = 100 K

  • 0.36 × 0.19 × 0.10 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]), based on expressions derived by Clark & Reid (1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.538, Tmax = 0.808

  • 10904 measured reflections

  • 3062 independent reflections

  • 2972 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.016

  • wR(F2) = 0.033

  • S = 1.05

  • 3062 reflections

  • 145 parameters

  • 6 restraints

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

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

  • Absolute structure: Refined as an inversion twin.

  • Flack parameter: 0.173 (17)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H11...N2i 0.86 (3) 1.95 (3) 2.805 (4) 173 (3)
N1-H12...O1ii 0.86 (3) 1.96 (3) 2.824 (3) 177 (4)
N1-H13...O2 0.91 (3) 1.81 (3) 2.716 (4) 172 (4)
N2-H21...O1 0.82 (3) 2.17 (3) 2.965 (4) 163 (4)
N2-H22...I1 0.83 (3) 3.21 (3) 3.948 (3) 150 (4)
Symmetry codes: (i) x, y, z-1; (ii) [-x+{\script{1\over 2}}, y, 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: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 2011)[Brandenburg, K. (2011). 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: ZL2559 ).


Acknowledgements

I would like to thank V. Breuers for valuable suggestions. Furthermore, I acknowledge the support for the publication fee by the Deutsche Forschungsgemeinschaft (DFG) and the open access publication fund of the Heinrich-Heine-Universität Düsseldorf.

References

Borisov, G., Varbanov, S. G., Venanzi, L. M., Albinati, A. & Demartin, F. (1994). Inorg. Chem. 33, 5430-5437.  [CrossRef] [ChemPort] [Web of Science]
Brandenburg, K. (2011). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Brunet, P., Simard, M. & Wuest, J. D. (1997). J. Am. Chem. Soc. 119, 2737-2738.  [CrossRef] [ChemPort] [Web of Science]
Buhl, D., Gün, H., Jablonka, A. & Reiss, G. J. (2013). Crystals 3, 350-362.  [CrossRef] [ChemPort]
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.  [CrossRef] [IUCr Journals]
Dodoff, N., Macicek, J., Angelova, O., Varbanov, S. G. & Spassovska, N. (1990). J. Coord. Chem. 22, 219-228.  [CrossRef] [ChemPort]
Grell, J., Bernstein, J. & Tinhofer, G. (2002). Crystallogr. Rev. 8, 1-56.  [CrossRef] [ChemPort]
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.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Reiss, G. J. (2013a). Acta Cryst. E69, m248-m249.  [CrossRef] [ChemPort] [IUCr Journals]
Reiss, G. J. (2013b). Acta Cryst. E69, m250-m251.  [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, A53, 819-828.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1253-o1254   [ doi:10.1107/S1600536813019004 ]

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