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Volume 69 
Part 6 
Pages o964-o965  
June 2013  

Received 10 May 2013
Accepted 17 May 2013
Online 25 May 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.041
wR = 0.096
Data-to-parameter ratio = 21.0
Details
Open access

2-[(Dimethylphenylphosphanylidene)azaniumyl]-5-methylbenzenesulfonate benzene monosolvate

aDepartment of Chemistry, University of Louisville, Louisville, KY 40292, USA
Correspondence e-mail: msmashuta.xray@louisville.edu

The title compound, C15H18NO3PS·C6H6, is a rare example of a crystallographically characterized exocyclic phosphiniminium-arenesulfonate zwitterion, which crystallises as its benzene solvate. The crystal structure shows that the N atom is protonated and that the iminium H atom forms both intra- and intermolecular hydrogen bonds to the single-bonded sulfonate O atom in an R22(4) graph-set motif. The dihedral angle between the aromatic rings in the main molecule is 89.49 (8)°.

Related literature

For background to this class of compound, see: Brown et al. (2007[Brown, M. K., May, T. L., Baxter, C. A. & Hoveyda, A. H. (2007). Angew. Chem. Int. Ed. 46, 1097-1100.]); Bruneau & Achard (2012[Bruneau, C. & Achard, M. (2012). Coord. Chem. Rev. 256, 525-536.]); Drent et al. (2002[Drent, E., van Dijk, R., van Ginkel, R., van Oort, B. & Pugh, R. I. (2002). Chem. Commun. pp. 744-745.]); Lee & Hoveyda (2009[Lee, Y. & Hoveyda, A. H. (2009). J. Am. Chem. Soc. 131, 3160-3161.]); Lee et al. (2008[Lee, Y., Akiyama, K., Gillingham, D. G., Brown, M. K. & Hoveyda, A. H. (2008). J. Am. Chem. Soc. 130, 446-447.], 2009[Lee, Y., Jang, H. & Hoveyda, A. H. (2009). J. Am. Chem. Soc. 131, 18234-18235.]); Nakamura et al. (2009[Nakamura, A., Ito, S. & Nozaki, K. (2009). Chem. Rev. 109, 5215-5244.]). For related structures, see: Burns et al. (2012[Burns, C. T., Shang, S., Thapa, R. & Mashuta, M. S. (2012). Tetrahedron Lett. 53, 4832-4835.]); Liu et al. (1995[Liu, C.-Y., Chen, D.-Y., Peng, S.-M., Cheng, M.-C. & Liu, S.-T. (1995). Organometallics, 14, 1983-1991.]); Perrotin et al. (2011[Perrotin, P., McCahill, J. S. J., Wu, G. & Scott, S. L. (2011). Chem. Commun. 47, 6948-6950.]); Spencer et al. (2003[Spencer, L. P., Altwer, R., Wei, P., Gelmini, L., Gauld, J. & Stephan, D. W. (2003). Organometallics, 22, 3841-3854.]); Wallis et al. (2009[Wallis, C. J., Kraft, I. L., Murphy, J. N., Patrick, B. O. & Mehrkhodavandi, P. (2009). Organometallics, 28, 3889-3895.], 2010[Wallis, C. J., Kraft, I. L., Patrick, B. O. & Mehrkhodavandi, P. (2010). Dalton Trans. 39, 541-547.]); Zhang et al. (2006[Zhang, C., Sun, W.-H. & Wang, Z.-X. (2006). Eur. J. Inorg. Chem. 23, 4895-4902.]); Zhou & Jordan (2011[Zhou, X. & Jordan, R. F. (2011). Organometallics, 30, 4632-4642.]). For hydrogen-bonding details, see: Desiraju (1995[Desiraju, G. R. (1995). Angew. Chem. Int. Ed. 34, 2311-2327.]).

[Scheme 1]

Experimental

Crystal data
  • C15H18NO3PS·C6H6

  • Mr = 401.44

  • Triclinic, [P \overline 1]

  • a = 9.3696 (2) Å

  • b = 10.3141 (2) Å

  • c = 11.7579 (3) Å

  • [alpha] = 68.665 (2)°

  • [beta] = 78.180 (2)°

  • [gamma] = 70.630 (2)°

  • V = 993.89 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.27 mm-1

  • T = 100 K

  • 0.41 × 0.31 × 0.25 mm

Data collection
  • Agilent Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.939, Tmax = 1.000

  • 22626 measured reflections

  • 5263 independent reflections

  • 4918 reflections with I > 2[sigma](I)

  • Rint = 0.017

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.096

  • S = 1.05

  • 5263 reflections

  • 251 parameters

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

  • [Delta][rho]max = 1.40 e Å-3

  • [Delta][rho]min = -0.42 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O2 0.80 (2) 2.09 (2) 2.7374 (17) 139 (2)
N1-H1N...O2i 0.80 (2) 2.47 (2) 3.0311 (17) 128 (2)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and 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: PK2483 ).


Acknowledgements

MSM thanks the Department of Energy, grant DEFG02-08CH11538, and the Kentucky Research Challenge Trust Fund for upgrade of our X-ray facilities. CTB thanks the American Chemical Society Petroleum Research Fund (grant 50401-DN13) for financial support of this research.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Brown, M. K., May, T. L., Baxter, C. A. & Hoveyda, A. H. (2007). Angew. Chem. Int. Ed. 46, 1097-1100.  [ISI] [CSD] [CrossRef] [ChemPort]
Bruneau, C. & Achard, M. (2012). Coord. Chem. Rev. 256, 525-536.  [ISI] [CrossRef] [ChemPort]
Burns, C. T., Shang, S., Thapa, R. & Mashuta, M. S. (2012). Tetrahedron Lett. 53, 4832-4835.  [ISI] [CSD] [CrossRef] [ChemPort]
Desiraju, G. R. (1995). Angew. Chem. Int. Ed. 34, 2311-2327.  [CrossRef] [ChemPort] [ISI]
Drent, E., van Dijk, R., van Ginkel, R., van Oort, B. & Pugh, R. I. (2002). Chem. Commun. pp. 744-745.  [CrossRef]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Lee, Y., Akiyama, K., Gillingham, D. G., Brown, M. K. & Hoveyda, A. H. (2008). J. Am. Chem. Soc. 130, 446-447.  [ISI] [CrossRef] [PubMed] [ChemPort]
Lee, Y. & Hoveyda, A. H. (2009). J. Am. Chem. Soc. 131, 3160-3161.  [ISI] [CrossRef] [PubMed] [ChemPort]
Lee, Y., Jang, H. & Hoveyda, A. H. (2009). J. Am. Chem. Soc. 131, 18234-18235.  [ISI] [CrossRef] [PubMed] [ChemPort]
Liu, C.-Y., Chen, D.-Y., Peng, S.-M., Cheng, M.-C. & Liu, S.-T. (1995). Organometallics, 14, 1983-1991.  [CrossRef] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Nakamura, A., Ito, S. & Nozaki, K. (2009). Chem. Rev. 109, 5215-5244.  [ISI] [CrossRef] [PubMed] [ChemPort]
Perrotin, P., McCahill, J. S. J., Wu, G. & Scott, S. L. (2011). Chem. Commun. 47, 6948-6950.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Spencer, L. P., Altwer, R., Wei, P., Gelmini, L., Gauld, J. & Stephan, D. W. (2003). Organometallics, 22, 3841-3854.  [CSD] [CrossRef] [ChemPort]
Wallis, C. J., Kraft, I. L., Murphy, J. N., Patrick, B. O. & Mehrkhodavandi, P. (2009). Organometallics, 28, 3889-3895.  [CSD] [CrossRef] [ChemPort]
Wallis, C. J., Kraft, I. L., Patrick, B. O. & Mehrkhodavandi, P. (2010). Dalton Trans. 39, 541-547.  [CSD] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zhang, C., Sun, W.-H. & Wang, Z.-X. (2006). Eur. J. Inorg. Chem. 23, 4895-4902.  [ISI] [CSD] [CrossRef]
Zhou, X. & Jordan, R. F. (2011). Organometallics, 30, 4632-4642.  [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o964-o965   [ doi:10.1107/S1600536813013755 ]

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