4-Meth­oxy­benzamidinium chloride monohydrate

Irrera, S.; Portalone, G.

doi:10.1107/S1600536812041219

Volume 68
Part 11
Page o3083
November 2012

Received 30 September 2012
Accepted 1 October 2012
Online 6 October 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R = 0.043
wR = 0.113
Data-to-parameter ratio = 20.8
Details

4-Methoxybenzamidinium chloride monohydrate

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

In the cation of the title compound, C₈H₁₁N₂O⁺·Cl^-·H₂O, the C-N bonds of the amidinium group are identical within experiemental error [1.305 (2) and 1.304 (2) Å], and its plane forms a dihedral angle of 25.83 (8)° with the phenyl ring. The ionic components are associated in the crystal into polymeric hydrogen-bonded supramolecular tapes stabilized by N-H⁺Cl^- and N-H⁺Ow intermolecular hydrogen bonds, and by Ow-HCl^- interactions.

Related literature

For the biological and pharmacological relevance of benzamidine, see: Marquart et al. (1983); Sprang et al. (1987); Bode et al. (1990); 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). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₈H₁₁N₂O⁺·Cl^-·H₂O
M_r = 204.65
Monoclinic, P 2₁ /c
a = 11.3029 (7) Å
b = 9.3142 (5) Å
c = 9.9983 (6) Å
= 99.820 (6)°
V = 1037.17 (11) Å³
Z = 4
Mo K radiation
= 0.34 mm^-1
T = 298 K
0.30 × 0.27 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur S CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.905, T_max = 0.968
7158 measured reflections
2989 independent reflections
1947 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.113
S = 0.97
2989 reflections
144 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.22 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1ACl1	0.81 (2)	2.85 (2)	3.5523 (18)	145 (2)
N1-H1BO2W	0.75 (2)	2.06 (2)	2.805 (2)	168 (2)
N2-H2ACl1	0.96 (2)	2.25 (2)	3.1850 (16)	164.4 (16)
N2-H2BCl1ⁱ	0.82 (2)	2.43 (2)	3.201 (2)	157.5 (18)
O2W-HWACl1ⁱⁱ	0.82 (3)	2.36 (3)	3.1731 (18)	170 (3)
O2W-HWBCl1ⁱⁱⁱ	0.87 (2)	2.29 (2)	3.1603 (17)	174.8 (19)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (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: QM2085 ).

References

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organic compounds