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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 [sigma](C-C) = 0.006 Å
R = 0.038
wR = 0.129
Data-to-parameter ratio = 14.9
Details
Open access

(Furfurylamino)triphenylphosphonium bromide

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-H...Br hydrogen bond and four weak C-H...Br contacts, forming a three-dimensional network.

Related literature

For (amino)phosphonium bromides derived from primary amines, see: Cao et al. (2010[Cao, T. P. A., Payet, E., Auffrant, A., Le Goff, X. F. & Le Floch, P. (2010). Organometallics, 29, 3991-3996.]); Boubekeur et al. (2006[Boubekeur, L., Ulmer, S., Ricard, L., Mézailles, N. & Le Floch, P. (2006). Organometallics, 25, 315-317.]); Dyer et al. (2011[Dyer, H., Picot, A., Vendier, L., Auffrant, A., Le Floch, P. & Sabo-Etienne, S. (2011). Organometallics, 30, 1478-1486.]); Horner & Oediger (1959[Horner, L. & Oediger, H. (1959). Liebigs Ann. Chem. 627, 142-162.]). For C-H...X hydrogen bonds, see: Jeffrey (1997[Jeffrey, G. A. (1997). An Introduction to Hydrogen Bonding, ch. 5. New York: Oxford University Press Inc.]); Zhang et al. (2003[Zhang, F., Lerner, H.-W. & Bolte, M. (2003). Acta Cryst. E59, o1181-o1182.]). For graph-set motifs, see: Bernstein, et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C23H21NOP+·Br-

  • Mr = 438.29

  • Triclinic, [P \overline 1]

  • a = 9.5190 (19) Å

  • b = 9.812 (2) Å

  • c = 12.726 (3) Å

  • [alpha] = 110.30 (3)°

  • [beta] = 104.89 (3)°

  • [gamma] = 96.81 (3)°

  • V = 1048.7 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.685, Tmax = 0.777

  • 11498 measured reflections

  • 3673 independent reflections

  • 3213 reflections with I > 2[sigma](I)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...Br1 0.81 (3) 2.49 (3) 3.293 (3) 170 (4)
C8-H8...Br1i 0.93 2.98 3.835 (4) 153
C15-H15...Br1ii 0.93 3.00 3.728 (4) 137
C21-H21...Br1iii 0.93 2.94 3.829 (6) 161
C23-H23...Br1iv 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[Siemens (1994). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: XSCANS; data reduction: SAINT-Plus NT (Bruker, 2001[Bruker (2001). SAINT-Plus NT. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]), publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact, Bonn, Germany.]).


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.  [CrossRef] [ChemPort] [ISI]
Boubekeur, L., Ulmer, S., Ricard, L., Mézailles, N. & Le Floch, P. (2006). Organometallics, 25, 315-317.  [CrossRef] [ChemPort]
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.  [CrossRef] [ChemPort]
Dyer, H., Picot, A., Vendier, L., Auffrant, A., Le Floch, P. & Sabo-Etienne, S. (2011). Organometallics, 30, 1478-1486.  [CrossRef] [ChemPort]
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.  [CrossRef] [details]
Siemens (1994). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zhang, F., Lerner, H.-W. & Bolte, M. (2003). Acta Cryst. E59, o1181-o1182.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o118  [ doi:10.1107/S1600536812050805 ]

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