(Furfuryl­amino)­triphenyl­phospho­nium bromide

Martínez de León, C.; Tlahuext, H.; Flores-Parra, A.; Duarte-Hernández, A.M.; Grévy, J.-M.

doi:10.1107/S1600536812050805

Volume 69
Part 1
Page o118
January 2013

Received 30 November 2012
Accepted 13 December 2012
Online 22 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R = 0.038
wR = 0.129
Data-to-parameter ratio = 14.9
Details

(Furfurylamino)triphenylphosphonium bromide

Carla Martínez de León,^a Hugo Tlahuext,^a Angelina Flores-Parra,^b Angélica María Duarte-Hernández ^b and Jean-Michel Grévy ^a ^*

^aCentro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos. Av. Universidad 1001 Col., Chamilpa, CP 62100, Cuernavaca Mor., Mexico, and ^bDepartamento de Química, Cinvestav México, 07000 Mexico DF, Mexico
Correspondence e-mail: jeanmichelg@gmail.com

In the title salt, C₂₃H₂₁NOP⁺·Br^-, the dihedral angles between the phenyl rings are 70.41 (18), 73.6 (2) and 80.85 (19)°. In the crystal, neighboring molecules are linked through an N-HBr hydrogen bond and four weak C-HBr contacts, forming a three-dimensional network.

Related literature

For (amino)phosphonium bromides derived from primary amines, see: Cao et al. (2010); Boubekeur et al. (2006); Dyer et al. (2011); Horner & Oediger (1959). For C-HX hydrogen bonds, see: Jeffrey (1997); Zhang et al. (2003). For graph-set motifs, see: Bernstein, et al. (1995).

Experimental

Crystal data

C₂₃H₂₁NOP⁺·Br^-
M_r = 438.29
Triclinic, $[P \overline 1]$
a = 9.5190 (19) Å
b = 9.812 (2) Å
c = 12.726 (3) Å
= 110.30 (3)°
= 104.89 (3)°
= 96.81 (3)°
V = 1048.7 (4) Å³
Z = 2
Mo K radiation
= 2.05 mm^-1
T = 293 K
0.20 × 0.17 × 0.13 mm

Data collection

Siemens P4 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.685, T_max = 0.777
11498 measured reflections
3673 independent reflections
3213 reflections with I > 2(I)
R_int = 0.046

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.129
S = 1.02
3673 reflections
247 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.32 e Å^-3
_min = -0.46 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1ABr1	0.81 (3)	2.49 (3)	3.293 (3)	170 (4)
C8-H8Br1ⁱ	0.93	2.98	3.835 (4)	153
C15-H15Br1ⁱⁱ	0.93	3.00	3.728 (4)	137
C21-H21Br1ⁱⁱⁱ	0.93	2.94	3.829 (6)	161
C23-H23Br1^iv	0.93	2.97	3.782 (4)	147
Symmetry codes: (i) x+1, y, z; (ii) -x, -y+1, -z+1; (iii) x, y+1, z; (iv) -x, -y+1, -z.

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SAINT-Plus NT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009), publCIF (Westrip, 2010) and DIAMOND (Brandenburg, 2006).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5227 ).

Acknowledgements

This work was supported by the Consejo Nacional de Ciencia y Tecnología (proyecto No. 134528, CB 2009-01)

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Boubekeur, L., Ulmer, S., Ricard, L., Mézailles, N. & Le Floch, P. (2006). Organometallics, 25, 315-317.
Brandenburg, K. (2006). DIAMOND. Crystal Impact, Bonn, Germany.
Bruker (2001). SAINT-Plus NT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cao, T. P. A., Payet, E., Auffrant, A., Le Goff, X. F. & Le Floch, P. (2010). Organometallics, 29, 3991-3996.
Dyer, H., Picot, A., Vendier, L., Auffrant, A., Le Floch, P. & Sabo-Etienne, S. (2011). Organometallics, 30, 1478-1486.
Horner, L. & Oediger, H. (1959). Liebigs Ann. Chem. 627, 142-162.
Jeffrey, G. A. (1997). An Introduction to Hydrogen Bonding, ch. 5. New York: Oxford University Press Inc.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1994). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.
Zhang, F., Lerner, H.-W. & Bolte, M. (2003). Acta Cryst. E59, o1181-o1182.

organic compounds