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Volume 69 
Part 1 
Page o56  
January 2013  

Received 3 December 2012
Accepted 5 December 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.027
wR = 0.055
Data-to-parameter ratio = 26.0
Details
Open access

4-Methoxybenzamidinium bromide

aChemistry Department, "Sapienza" University of Rome, P.le A. Moro, 5, I-00185 Rome, Italy
Correspondence e-mail: g.portalone@caspur.it

The title salt, C8H11N2O+·Br-, was synthesized by the reaction between 4-methoxybenzamidine (4-amidinoanisole) and hydrobromic acid. In the cation, the amidinium group has two similar C-N bonds [1.304 (2) and 1.316 (2) Å], and its plane forms a dihedral angle of 31.08 (5)° with the benzene ring. The ions are associated in the crystal into a three-dimension hydrogen-bonded supramolecular network featuring N-H+...Br- interactions.

Related literature

For the biological and pharmacological relevance of benzamidine, see: Powers & Harper (1999[Powers, J. C. & Harper, J. W. (1999). Proteinase Inhibitors, edited by A. J. Barrett & G. Salvesen, pp. 55-152. Amsterdam: Elsevier.]). For structural analysis of proton-transfer adducts containing molecules of biological interest, see: Portalone (2011[Portalone, G. (2011). Chem. Centr. J. 5, 51.]); Portalone & Irrera (2011[Portalone, G. & Irrera, S. (2011). J. Mol. Struct. 991, 92-96.]). For the supramolecular association in proton-transfer adducts containing benzamidinium cations, see: Portalone (2010[Portalone, G. (2010). Acta Cryst. C66, o295-o301.], 2012[Portalone, G. (2012). Acta Cryst. E68, o268-o269.]); Irrera et al. (2012[Irrera, S., Ortaggi, G. & Portalone, G. (2012). Acta Cryst. C68, o447-o451.]); Irrera & Portalone (2012a[Irrera, S. & Portalone, G. (2012a). Acta Cryst. E68, o3083.],b[Irrera, S. & Portalone, G. (2012b). Acta Cryst. E68, o3244.],c[Irrera, S. & Portalone, G. (2012c). Acta Cryst. E68, o3277.],d[Irrera, S. & Portalone, G. (2012d). Acta Cryst. E68, o3334.],e[Irrera, S. & Portalone, G. (2012e). Acta Cryst. E68, o3350-o3351.]). For hydrogen-bond 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
  • C8H11N2O+·Br-

  • Mr = 231.10

  • Orthorhombic, P 21 21 21

  • a = 7.5657 (6) Å

  • b = 10.8711 (7) Å

  • c = 11.5419 (7) Å

  • V = 949.29 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 4.29 mm-1

  • T = 298 K

  • 0.18 × 0.12 × 0.10 mm

Data collection
  • Agilent Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.513, Tmax = 0.674

  • 34724 measured reflections

  • 3278 independent reflections

  • 2903 reflections with I > 2[sigma](I)

  • Rint = 0.043

Refinement
  • R[F2 > 2[sigma](F2)] = 0.027

  • wR(F2) = 0.055

  • S = 1.09

  • 3278 reflections

  • 126 parameters

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

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1387 Friedel pairs

  • Flack parameter: -0.002 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...Br1 0.87 (3) 2.48 (3) 3.3163 (19) 159 (2)
N1-H1B...Br1i 0.88 (3) 2.49 (3) 3.3676 (19) 176 (2)
N2-H2A...Br1 0.95 (3) 2.65 (3) 3.4765 (17) 145 (2)
N2-H2B...Br1ii 0.78 (2) 2.70 (3) 3.4742 (17) 175 (2)
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5032 ).


References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Irrera, S., Ortaggi, G. & Portalone, G. (2012). Acta Cryst. C68, o447-o451.  [CrossRef] [details]
Irrera, S. & Portalone, G. (2012a). Acta Cryst. E68, o3083.  [CSD] [CrossRef] [details]
Irrera, S. & Portalone, G. (2012b). Acta Cryst. E68, o3244.  [CSD] [CrossRef] [details]
Irrera, S. & Portalone, G. (2012c). Acta Cryst. E68, o3277.  [CSD] [CrossRef] [details]
Irrera, S. & Portalone, G. (2012d). Acta Cryst. E68, o3334.  [CSD] [CrossRef] [details]
Irrera, S. & Portalone, G. (2012e). Acta Cryst. E68, o3350-o3351.  [CSD] [CrossRef] [ChemPort] [details]
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Portalone, G. (2010). Acta Cryst. C66, o295-o301.  [CSD] [CrossRef] [details]
Portalone, G. (2011). Chem. Centr. J. 5, 51.  [CSD] [CrossRef]
Portalone, G. (2012). Acta Cryst. E68, o268-o269.  [CSD] [CrossRef] [details]
Portalone, G. & Irrera, S. (2011). J. Mol. Struct. 991, 92-96.  [ISI] [CSD] [CrossRef] [ChemPort]
Powers, J. C. & Harper, J. W. (1999). Proteinase Inhibitors, edited by A. J. Barrett & G. Salvesen, pp. 55-152. Amsterdam: Elsevier.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o56  [ doi:10.1107/S1600536812049872 ]

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