3,4-Dimethyl­anilinium chloride monohydrate

Sofiane Bouacida; Ratiba Belhouas; Habiba Kechout; Hocine Merazig; Patricia Bénard-Rocherullé

doi:10.1107/S1600536809006072

. 2009 Feb 28;65(Pt 3):o628–o629. doi: 10.1107/S1600536809006072

3,4-Dimethylanilinium chloride monohydrate

Sofiane Bouacida ^a,^b,^*, Ratiba Belhouas ^c, Habiba Kechout ^b, Hocine Merazig ^b, Patricia Bénard-Rocherullé ^d

PMCID: PMC2968595 PMID: 21582279

Abstract

The crystal structure of the title compound, C₈H₁₂N⁺·Cl⁻·H₂O, consists of hydrophobic layers of dimethylanilinium cations parallel to the bc plane alternated by hydrophilic layers of chloride anions and water molecules. The layers are linked by N—H⋯O and N—H⋯Cl hydrogen bonds involving the ammonium groups of the cations. The cohesion of the ionic structure is further stabilized by O—H⋯Cl hydrogen-bonding interactions.

Related literature

For crystal structures containing the dimethylanilinium cation, see: Bouacida (2008 ▶); Singh et al. (2002 ▶); Singh et al. (1995a ▶,b ▶); Linden et al. (1995 ▶); Fábry et al. (2001 ▶, 2002 ▶). For the crystal structures of related protonated amines, see: Bouacida et al. (2005a ▶,b ▶,c ▶, 2006 ▶, 2007 ▶); Benslimane et al. (2007 ▶); Rademeyer (2004a ▶,b ▶).

Experimental

Crystal data

C₈H₁₂N⁺·Cl⁻·H₂O
M _r = 175.65
Orthorhombic,
a = 18.230 (18) Å
b = 6.7854 (14) Å
c = 7.916 (2) Å
V = 979.2 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 295 K
0.1 × 0.04 × 0.02 mm

Data collection

Enraf–Nonius KappaCCD diffractometer
Absorption correction: none
10115 measured reflections
2181 independent reflections
1403 reflections with I > 2σ(I)
R _int = 0.078

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.109
S = 1.15
2181 reflections
109 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ▶), 976 Friedel pairs
Flack parameter: 0.01 (11)

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶); and SCALEPACK program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg et al., 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006072/rz2296sup1.cif

e-65-0o628-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006072/rz2296Isup2.hkl

e-65-0o628-Isup2.hkl^{(105KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1W	0.89	1.87	2.754 (5)	174
N1—H1B⋯Cl1ⁱ	0.89	2.30	3.177 (4)	167
N1—H1C⋯Cl1ⁱⁱ	0.89	2.31	3.181 (4)	167
O1W—H1W⋯Cl1	0.80 (6)	2.43 (6)	3.217 (5)	174 (7)
O1W—H2W⋯Cl1ⁱⁱⁱ	0.81 (5)	2.36 (5)	3.174 (5)	176 (2)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The authors are grateful to Dr Thierry Roisnel, Centre de Diffractométrie X (CDIFX) de Rennes, Université de Rennes 1, France, for the data collection facilities. SB thanks Université A. Mira de Béjaia, Algéria, for financial support.

supplementary crystallographic information

Comment

The title compound, was prepared as part of our ongoing studies of hydrogen-bonding interactions in the crystal structure of protonated amines (Bouacida et al., 2005a,b,c; Bouacida et al., 2006; Benslimane et al., 2007; Bouacida et al., 2007). Structures containing the dimethylanilinium cation have been already reported with tin chloride (Bouacida, 2008), sulfate (Singh et al., 2002), nitrate and perchlorate (Singh et al., 1995a,b), chloride (Linden et al., 1995), and dihydrogenphosphate (Fabry et al., 2001; Fábry et al., 2002).

The molecular structure of the title compound is illustrated in Fig. 1. A l l bond distances and angles are within the ranges of accepted values. The amino N atom is protonated as in other aminoacids (Bouacida et al., 2006; Rademeyer 2004a,b). A diagram of the layered crystal packing of title compound is shown in Fig. 2, in which the cations are arranged to form zigzag layers parallel the ab plane, with the chloride ions and water molecules located between these layers. The structure may be also described as formed by hydrophobic layers parallel to the bc plane of dimethylanilinium cations alternated by hydrophilic layers of chloride anions and water molecules. In this structure, three types of classical hydrogen bonds are observed, viz. cation–anion, cation–water and water–anion (Fig. 3, Table 1). All three ammonium H atoms are involved in hydrogen bonds. These interactions link the molecules within the layers and also link the layers together, forming a three-dimensional network and reinforcing the cohesion of the ionic structure.

Experimental

An aqueous solution of SnCl₂.2H₂O (1 mmol) and 3,4-dimethylaniline (2 mmol) in hydrochloric acid was slowly evaporated to dryness for two weeks. White single crystals of the title compound were carefully isolated under polarizing microscope for X-ray diffraction analysis