4-Meth­oxy­benzamidinium acetate

Irrera, S.; Portalone, G.

doi:10.1107/S1600536812044911

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 (C-C) = 0.003 Å
R = 0.056
wR = 0.141
Data-to-parameter ratio = 15.2
Details

4-Methoxybenzamidinium acetate

Simona Irrera ^a and Gustavo Portalone ^a ^*

^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). For structural analysis of proton-transfer adducts containing molecules of biological interest, see: Portalone, (2011a); Portalone & Irrera (2011). For the supramolecular association in proton-transfer adducts containing benzamidinium cations, see; Portalone (2010, 2011b, 2012); Irrera & Portalone (2012a,b); Irrera et al. (2012). For hydrogen-bond motifs, see Bernstein et al. (1995). For standard bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₈H₁₁N₂O⁺·C₂H₃O₂^-
M_r = 210.23
Monoclinic, P 2₁ /n
a = 8.7591 (14) Å
b = 6.5478 (8) Å
c = 19.456 (3) Å
= 102.580 (14)°
V = 1089.0 (3) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.980, T_max = 0.986
14433 measured reflections
2365 independent reflections
1834 reflections with I > 2(I)
R_int = 0.040

Refinement

R[F² > 2(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
_max = 0.21 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO1	0.91 (3)	1.94 (3)	2.847 (2)	175 (2)
N1-H1BO1ⁱ	0.91 (2)	1.98 (2)	2.832 (2)	155 (2)
N2-H2AO2	0.94 (3)	1.83 (3)	2.776 (2)	176 (2)
N2-H2BO2ⁱⁱ	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
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Portalone, G. (2010). Acta Cryst. C66, o295-o301.
Portalone, G. (2011a). Chem. Centr. J. 5, 51.
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Portalone, G. (2012). Acta Cryst. E68, o268-o269.
Portalone, G. & Irrera, S. (2011). J. Mol. Struct. 991, 92-96.
Powers, J. C. & Harper, J. W. (1999). Proteinase inhibitors, edited by A. J. Barrett & G. Salvesen, pp. 55-152. Elsevier: Amsterdam.
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organic compounds