4-Meth­oxy­benzamidinium hydrogen sulfate

Irrera, S.; Portalone, G.

doi:10.1107/S1600536812044327

Volume 68
Part 11
Page o3244
November 2012

Received 23 October 2012
Accepted 25 October 2012
Online 31 October 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R = 0.039
wR = 0.114
Data-to-parameter ratio = 15.7
Details

4-Methoxybenzamidinium hydrogen sulfate

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 salt, C₈H₁₁N₂O⁺·HSO₄^-, has been synthesized by the reaction between 4-methoxybenzamidine and sulfuric acid. The asymmetric unit comprises a nonplanar 4-methoxybenzamidinium cation and one hydrogen sulfate anion. In the cation, the amidinium group has two identical C-N bonds [1.306 (2) and 1.308 (2) Å], and its plane forms a dihedral angle of 6.49 (8)° with the mean plane of the benzene ring. The ionic components are associated in the crystal via N-H⁺O^-, resulting in chains running approximately along the b-axis direction whicg are interconnected by O-HO^- hydrogen bonds.

Related literature

For the biological and pharmacological relevance of benzamidine, see: Powers & Harper (1999); Grzesiak et al. (2000). 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 (2012); Irrera et al. (2012). For hydrogen-bond motifs, see Bernstein et al. (1995).

Experimental

Crystal data

C₈H₁₁N₂O⁺·HSO₄^-
M_r = 248.26
Monoclinic, P 2₁ /c
a = 14.2608 (14) Å
b = 10.1844 (9) Å
c = 7.5723 (9) Å
= 94.206 (10)°
V = 1096.83 (19) Å³
Z = 4
Mo K radiation
= 0.30 mm^-1
T = 298 K
0.31 × 0.25 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur S CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.912, T_max = 0.956
16529 measured reflections
2626 independent reflections
2133 reflections with I > 2(I)
R_int = 0.036

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.114
S = 1.04
2626 reflections
167 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.26 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3AO2ⁱ	0.78 (3)	1.79 (3)	2.562 (2)	172 (3)
N1-H1AO4	0.86 (2)	2.10 (2)	2.938 (2)	163 (2)
N1-H1BO5ⁱⁱ	0.84 (2)	2.10 (2)	2.884 (2)	154 (2)
N2-H2AO5	0.84 (2)	2.07 (3)	2.907 (2)	177 (2)
N2-H2BO4ⁱⁱⁱ	0.86 (3)	2.22 (3)	2.965 (2)	145 (3)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; 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: RZ5020 ).

References

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organic compounds