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

Burke, B.P.; Greenman, P.; Smith, A.M.; Archibald, S.J.

doi:10.1107/S1600536812042341

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 (C-C) = 0.005 Å
R = 0.029
wR = 0.051
Data-to-parameter ratio = 15.4
Details

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

Benjamin P. Burke,^a Peter Greenman,^a Adam M. Smith ^a and Stephen J. Archibald ^a ^*

^aDepartment of Chemistry, University of Hull, Hull, HU6 7RX, UK
Correspondence e-mail: s.j.archibald@hull.ac.uk

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-HBr hydrogen bonds. There is also a C-HN 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 & Singh (2002); Wang et al. (2007); Kim et al. (2008, 2012); Madar et al. (2007). For the synthesis of triphenylphosphonium salts, see: Wang et al. (2007).

Experimental

Crystal data

C₂₆H₂₃BrP·Br·C₂H₃N
M_r = 567.29
Triclinic, $[P \overline 1]$
a = 9.588 (2) Å
b = 12.333 (3) Å
c = 12.393 (3) Å
= 74.961 (19)°
= 70.051 (18)°
= 69.293 (19)°
V = 1272.4 (5) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.336, T_max = 0.661
9761 measured reflections
4473 independent reflections
2659 reflections with I > 2(I)
R_int = 0.069

Refinement

R[F² > 2(F²)] = 0.029
wR(F²) = 0.051
S = 0.68
4473 reflections
290 parameters
H-atom parameters constrained
_max = 0.41 e Å^-3
_min = -0.36 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C1-H1BN1ⁱ	0.99	2.60	3.488 (6)	150
C8-H8ABr2ⁱⁱ	0.99	2.64	3.625 (4)	172
C8-H8BBr2ⁱⁱⁱ	0.99	2.79	3.753 (3)	166
C20-H20Br2ⁱⁱⁱ	0.95	2.81	3.746 (4)	169
C28-H28CBr2	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); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999).

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).

References

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

organic compounds