[Journal logo]

Volume 68 
Part 11 
Page o3202  
November 2012  

Received 4 October 2012
Accepted 9 October 2012
Online 24 October 2012

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.005 Å
R = 0.029
wR = 0.051
Data-to-parameter ratio = 15.4
Details
Open access

[4-(Bromomethyl)benzyl]triphenylphosphonium bromide acetonitrile monosolvate

In the title compound, C26H23BrP+·Br-·C2H3N, the dihedral angles between the plane of the benzylic phenyl ring attached to the P atom and the planes of the three directly attached phenyl rings are 34.04 (12), 45.48 (13) and 87.18 (9)°. In the crystal, centrosymmetric pairs of cations and anions are linked into dimeric aggregates via C-H...Br hydrogen bonds. There is also a C-H...N hydrogen bond to the acetonitrile solvent molecule.

Related literature

For background to the biological activity of alkyltriphenylphosphonium derivatives, see: Modica-Napolitano & Aprille (2001[Modica-Napolitano, J. S. & Aprille, J. R. (2001). Adv. Drug. Del. Rev. 49, 63-70.]); Modica-Napolitano & Singh (2002[Modica-Napolitano, J. S. & Singh, K. K. (2002). Exp. Rev. Mol. Med. 4, 1-19.]); Wang et al. (2007[Wang, J., Yang, C.-T., Kim, Y.-S., Sreerama, S. G., Cao, Q., Li, Z.-B., He, Z., Chen, X. & Liu, S. (2007). J. Med. Chem. 50, 5057-5059.]); Kim et al. (2008[Kim, Y.-S., Yang, C.-T., Wang, J., Wang, L., Li, Z.-B., Chen, X. & Liu, S. (2008). J. Med. Chem. 51, 2971-2984.], 2012[Kim, D.-Y., Kim, H.-J., Yu, K.-H. & Min, J.-J. (2012). Bioconj. Chem. 23, 431-437.]); Madar et al. (2007[Madar, I., Ravert, H., DiPaula, A., Du, Y., Dannals, R. F. & Becker, L. (2007). J. Nucl. Med. 48, 1021-1030.]). For the synthesis of triphenylphosphonium salts, see: Wang et al. (2007[Wang, J., Yang, C.-T., Kim, Y.-S., Sreerama, S. G., Cao, Q., Li, Z.-B., He, Z., Chen, X. & Liu, S. (2007). J. Med. Chem. 50, 5057-5059.]).

[Scheme 1]

Experimental

Crystal data
  • C26H23BrP·Br·C2H3N

  • Mr = 567.29

  • Triclinic, [P \overline 1]

  • a = 9.588 (2) Å

  • b = 12.333 (3) Å

  • c = 12.393 (3) Å

  • [alpha] = 74.961 (19)°

  • [beta] = 70.051 (18)°

  • [gamma] = 69.293 (19)°

  • V = 1272.4 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 3.26 mm-1

  • T = 150 K

  • 0.2 × 0.2 × 0.1 mm

Data collection
  • Stoe IPDSII diffractometer

  • Absorption correction: integration (X-AREA; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED. Stoe & Cie GmbH, Darmstadt, Germany.]) Tmin = 0.336, Tmax = 0.661

  • 9761 measured reflections

  • 4473 independent reflections

  • 2659 reflections with I > 2[sigma](I)

  • Rint = 0.069

Refinement
  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.051

  • S = 0.68

  • 4473 reflections

  • 290 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.41 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1B...N1i 0.99 2.60 3.488 (6) 150
C8-H8A...Br2ii 0.99 2.64 3.625 (4) 172
C8-H8B...Br2iii 0.99 2.79 3.753 (3) 166
C20-H20...Br2iii 0.95 2.81 3.746 (4) 169
C28-H28C...Br2 0.98 2.69 3.673 (5) 176
Symmetry codes: (i) -x, -y+2, -z; (ii) -x, -y+1, -z+1; (iii) x, y+1, z.

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED. Stoe & Cie GmbH, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED. Stoe & Cie GmbH, Darmstadt, Germany.]); 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5012 ).


Acknowledgements

We acknowledge the EPSRC for funds which enabled the purchase of the Stoe IPDSII diffractometer. We thank the University of Hull for the provision of a scholarship for BPB and the Nuffield Foundation for sponsorship of PG via the CREST programme. We acknowledge the use of the EPSRC's Chemical Database Service at Daresbury (Fletcher et al., 1996[Fletcher, D. A., McMeeking, R. F. & Parkin, D. (1996). J. Chem. Inf. Comput. Sci. 36, 746-749.]).

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Fletcher, D. A., McMeeking, R. F. & Parkin, D. (1996). J. Chem. Inf. Comput. Sci. 36, 746-749.  [CrossRef] [ChemPort] [ISI]
Kim, D.-Y., Kim, H.-J., Yu, K.-H. & Min, J.-J. (2012). Bioconj. Chem. 23, 431-437.  [CrossRef] [ChemPort]
Kim, Y.-S., Yang, C.-T., Wang, J., Wang, L., Li, Z.-B., Chen, X. & Liu, S. (2008). J. Med. Chem. 51, 2971-2984.  [ISI] [CrossRef] [PubMed] [ChemPort]
Madar, I., Ravert, H., DiPaula, A., Du, Y., Dannals, R. F. & Becker, L. (2007). J. Nucl. Med. 48, 1021-1030.  [CrossRef] [PubMed] [ChemPort]
Modica-Napolitano, J. S. & Aprille, J. R. (2001). Adv. Drug. Del. Rev. 49, 63-70.  [ChemPort]
Modica-Napolitano, J. S. & Singh, K. K. (2002). Exp. Rev. Mol. Med. 4, 1-19.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Stoe & Cie (2002). X-AREA and X-RED. Stoe & Cie GmbH, Darmstadt, Germany.
Wang, J., Yang, C.-T., Kim, Y.-S., Sreerama, S. G., Cao, Q., Li, Z.-B., He, Z., Chen, X. & Liu, S. (2007). J. Med. Chem. 50, 5057-5059.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o3202  [ doi:10.1107/S1600536812042341 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.