N-(2,6-Dimethyl­anilino)-5,6-dihydro-4H-1,3-thia­zin-3-ium chloride monohydrate

Mikelis V Veidis; Liana Orola; Reinis Arajs

doi:10.1107/S160053680801372X

. 2008 May 10;64(Pt 6):o1062. doi: 10.1107/S160053680801372X

N-(2,6-Dimethylanilino)-5,6-dihydro-4H-1,3-thiazin-3-ium chloride monohydrate

Mikelis V Veidis ^a,^*, Liana Orola ^a, Reinis Arajs ^a

PMCID: PMC2961393 PMID: 21202581

Abstract

In the title compound, alternatively called xylazine hydrochloride monohydrate, C₁₂H₁₇N₂S⁺·Cl⁻·H₂O, the six-membered thiazine ring is in a half-chair conformation. In the crystal structure, six component centrosymmetric clusters are formed via intermolecular O—H⋯Cl, N—H⋯O and N—H⋯Cl hydrogen bonds involving xylazine cations, chloride anions and water molecules.

Related literature

For related literature see: Carpy et al. (1979 ▶); Kalman et al. (1977 ▶).

Experimental

Crystal data

C₁₂H₁₇N₂S⁺·Cl⁻·H₂O
M _r = 274.81
Monoclinic,
a = 13.4546 (2) Å
b = 8.6547 (1) Å
c = 12.7732 (2) Å
β = 109.210 (2)°
V = 1404.56 (4) Å³
Z = 4
Cu Kα radiation
μ = 3.69 mm⁻¹
T = 100 K
0.44 × 0.25 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: numerical (de Meulenaer & Tompa, 1965 ▶) T _min = 0.30, T _max = 0.61
19046 measured reflections
2747 independent reflections
2509 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.088
S = 1.01
2509 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: CRYSTALS.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801372X/lh2620sup1.cif

e-64-o1062-sup1.cif^{(15.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801372X/lh2620Isup2.hkl

e-64-o1062-Isup2.hkl^{(137.5KB, 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
N5—H5⋯O17	0.87	1.97	2.815 (2)	163
O17—H171⋯Cl16ⁱ	0.82	2.36	3.158 (1)	164
N7—H7⋯Cl16ⁱ	0.87	2.37	3.204 (1)	162
O17—H172⋯Cl16ⁱⁱ	0.83	2.35	3.171 (1)	173

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

Acknowledgments

We thank Oxford Diffraction Ltd for the low-temperature data collection and reduction. Cooperation of the University of Cincinnati Crystallography Centre and the Latvia Institute of Organic Synthesis is acknowledged. Financial aid was provided by Latvia Science Council grant 05.1737.

supplementary crystallographic information

Comment

Xylazine hydrochloride monohydrate is a pharmaceutical used in veterinary medicine as an anesthetic. The substance is an alpha2-agonist with sedative, analgesic, and muscle relaxing properties.

The crystal structure of the title compound has been determined at 100 K. The structure is depicted in Fig. 1. The phenyl ring forms a dihedral angle of 83.24 (14)° with the plane defined by S1, C6 and N5 of the thiazine ring. The six-member thiazine ring assumes the half-chair conformation.

Hydrogen atoms are bonded to both nitrogen atoms forming a cation. Both hydrogen atoms participate in hydrogen bonding. The two xylazine moieties are held together through an extended H-bond network involving the nitrogen, oxygen, and chlorine anions. In the crystal structure, centrosymmetric clusters are formed by N—H···O—H···Cl···H—N hydrogen bond sequence between the two xylazine moieties.

There are H-bonds which do not join the xylazine moities between oxygen and chlorine (Fig. 2). These may impart additional rigidity in the cluster. As a result of Cl···H—O hydrogen bonding a parallelogram is formed by the Cl—O—Cl—O atoms.

The hydrogen bond lengths are given in the Table 1.

Experimental

The title compound was supplied by Grindeks Company. For crystal structure determination suitable crystals were grown by slow evaporation of an ethanol (96%) solution at room temperature.