2,6-Dimethyl­anilinium chloride monohydrate

Wajda Smirani; Olfa Amri; Mohamed Rzaigui

doi:10.1107/S1600536808039159

. 2008 Nov 29;64(Pt 12):o2463. doi: 10.1107/S1600536808039159

2,6-Dimethylanilinium chloride monohydrate

Wajda Smirani ^a,^*, Olfa Amri ^a, Mohamed Rzaigui ^a

PMCID: PMC2960140 PMID: 21581431

Abstract

In the title hydrated molecular salt, C₈H₁₂N⁺·Cl⁻·H₂O, the component species interact by way of N—H⋯O, N—H⋯Cl and O—H⋯Cl hydrogen bonds, resulting in a three-dimensional network.

Related literature

For related structures, see: Abid et al. (2007 ▶); Mrad et al. (2006 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₈H₁₂N⁺·Cl⁻·H₂O
M _r = 175.65
Monoclinic,
a = 8.676 (3) Å
b = 14.144 (3) Å
c = 7.913 (6) Å
β = 101.88 (5)°
V = 950.2 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 293 (2) K
0.20 × 0.13 × 0.10 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer
Absorption correction: none
3722 measured reflections
2244 independent reflections
1827 reflections with I > 2σ(I)
R _int = 0.033
2 standard reflections frequency: 120 min intensity decay: 5%

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.080
S = 1.04
2244 reflections
156 parameters
H-atom parameters not refined
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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 Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808039159/hb2860sup1.cif

e-64-o2463-sup1.cif^{(15.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039159/hb2860Isup2.hkl

e-64-o2463-Isup2.hkl^{(107.3KB, 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
O1—H1⋯Cl1	0.90 (2)	2.41 (2)	3.305 (3)	173 (2)
O1—H2⋯Cl1ⁱ	0.87 (3)	2.32 (3)	3.163 (3)	165 (2)
N1—H6⋯Cl1ⁱⁱ	0.893 (18)	2.392 (18)	3.235 (3)	157.5 (15)
N1—H7⋯O1	0.896 (16)	1.835 (16)	2.731 (3)	177.3 (17)
N1—H8⋯Cl1ⁱⁱⁱ	0.883 (16)	2.414 (16)	3.265 (3)	162.8 (15)

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

supplementary crystallographic information

Comment

As part of our ongoing studies of organic-inorganic hybrid networks containing the 2,6-xylidinium cation (Mrad et al., 2006; Abid et al., 2007) we now report the synthesis and structure of the title compound, (I).

As shown in Fig. 1, the asymmetric unit of (I) contains a 2,6-xylidinium cation, a chloride anion and a water molecule. A perspective view of the structure along the a axis is given in Fig. 2. It shows that two 2,6-xylidinium cations are interconnected through two chloride anions into dimers via two N—H···Cl bonds, characterized by N···Cl separations of 3.264 (3) and 3.235 (3) Å) and forming an 8-membered ring with graph-set R₂⁴(8) (Bernstein et al., 1995).

The title compound is a crystalline hydrate including one water of crystallization, which interconnect these dimers to each other to form layers parallel to the (b, c) plane, through N—H···O and O—H···Cl hydrogen bonds (Table 1).

Hydrogen bonds, electrostatic and van der Waals interactions participate to the cohesion of the three-dimensional network and add stability to this compound (Fig. 2). An examination of the organic group moiety geometrical features shows that the C—C and C—N bond lengths and the C—C—C and C—C—N angles are in the range usually found for this molecule (Abid et al., 2007).

Experimental

2,6-xylidinie and HCl were mixed in water in a 1: 1 molar ratio. The obtained solution was slowly evapored at room temperature to yield colourless blocks of (I).