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Volume 68 
Part 12 
Page o3277  
December 2012  

Received 29 October 2012
Accepted 30 October 2012
Online 3 November 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.056
wR = 0.141
Data-to-parameter ratio = 15.2
Details
Open access

4-Methoxybenzamidinium acetate

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

The title compound, C8H11N2O+·CH3CO2-, was synthesized by a reaction between 4-methoxybenzamidine (4-amidinoanisole) and acetic acid. In the cation, the amidinium group forms a dihedral angle of 11.65 (17)° with the mean plane of the benzene ring. The ionic components are associated in the crystal via N-H+...O- hydrogen bonds, resulting in a one-dimensional structure consisting of dimers and catemers and orientated approximately along the c axis.

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. Elsevier: Amsterdam.]). For structural analysis of proton-transfer adducts containing molecules of biological interest, see: Portalone, (2011a[Portalone, G. (2011a). 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.], 2011b[Portalone, G. (2011b). Acta Cryst. E67, o3394-o3395.], 2012[Portalone, G. (2012). Acta Cryst. E68, o268-o269.]); Irrera & Portalone (2012a[Irrera, S. & Portalone, G. (2012a). Acta Cryst. E68, o3083.],b[Irrera, S. & Portalone, G. (2012b). Acta Cryst. E68, o3244.]); Irrera et al. (2012[Irrera, S., Ortaggi, G. & Portalone, G. (2012). Acta Cryst. C68, o447-o451.]). 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.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C8H11N2O+·C2H3O2-

  • Mr = 210.23

  • Monoclinic, P 21 /n

  • a = 8.7591 (14) Å

  • b = 6.5478 (8) Å

  • c = 19.456 (3) Å

  • [beta] = 102.580 (14)°

  • V = 1089.0 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 298 K

  • 0.21 × 0.18 × 0.15 mm

Data collection
  • Oxford Diffraction Xcalibur S CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.980, Tmax = 0.986

  • 14433 measured reflections

  • 2365 independent reflections

  • 1834 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.141

  • S = 1.08

  • 2365 reflections

  • 156 parameters

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

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O1 0.91 (3) 1.94 (3) 2.847 (2) 175 (2)
N1-H1B...O1i 0.91 (2) 1.98 (2) 2.832 (2) 155 (2)
N2-H2A...O2 0.94 (3) 1.83 (3) 2.776 (2) 176 (2)
N2-H2B...O2ii 0.88 (2) 1.95 (2) 2.817 (2) 168 (2)
Symmetry codes: (i) -x, -y, -z+1; (ii) [-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: 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: TK5166 ).


References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
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. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [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]
Portalone, G. (2010). Acta Cryst. C66, o295-o301.  [CSD] [CrossRef] [details]
Portalone, G. (2011a). Chem. Centr. J. 5, 51.  [CSD] [CrossRef]
Portalone, G. (2011b). Acta Cryst. E67, o3394-o3395.  [CSD] [CrossRef] [details]
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. Elsevier: Amsterdam.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3277  [ doi:10.1107/S1600536812044911 ]

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