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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680801372X/lh2620sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680801372X/lh2620Isup2.hkl
Contains datablock I

CCDC reference: 667774

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.033
  • wR factor = 0.089
  • Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level A DIFF020_ALERT_1_A _diffrn_standards_interval_count and _diffrn_standards_interval_time are missing. Number of measurements between standards or time (min) between standards.
Author Response: Area detector was employed, no standards measured.
DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.
Author Response: No standards measured.

Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 -- C10 .. 5.50 su PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
2 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

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.

Related literature top

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

Experimental top

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.

Refinement top

The hydrogen atoms were located by difference Fourier method. During refinement hydrogen atoms were costrained to the riding mode. Uiso(H)=xUeq(C,N,O), where the average values of x are 1.15 for H atoms bonded to the thiazine ring, 1.48 for methyl H atoms, 1.16 for benzene ring H atoms, 1.17 fot the H atoms bonded to the nitrogen atoms and 1.44 for the H atoms of the water molecule.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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 (Betteridge et al., 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with thermal ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Intermolecular hydrogen bond formation (dashed lines) in the title compound.
N-(2,6-Dimethylanilino)-5,6-dihydro-4H-1,3-thiazin-3-ium chloride monohydrate top
Crystal data top
C12H17N2S+·Cl·H2OF(000) = 584
Mr = 274.81Dx = 1.300 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybcCell parameters from 19046 reflections
a = 13.4546 (2) Åθ = 3.5–74.6°
b = 8.6547 (1) ŵ = 3.69 mm1
c = 12.7732 (2) ÅT = 100 K
β = 109.210 (2)°Prism, white
V = 1404.56 (4) Å30.44 × 0.25 × 0.14 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur
diffractometer
2747 independent reflections
Radiation source: Enhance (Cu) X-ray Source2509 reflections with I > 2.0σ(I)
Graphite monochromatorRint = 0.029
ϕ and ω scansθmax = 74.6°, θmin = 3.5°
Absorption correction: numerical
(de Meulenaer & Tompa, 1965)
h = 1616
Tmin = 0.30, Tmax = 0.61k = 1010
19046 measured reflectionsl = 1515
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.033 W = [weight][1-(δF/6σF)2]2
wR(F2) = 0.088(Δ/σ)max = 0.000294
S = 1.02Δρmax = 0.43 e Å3
2509 reflectionsΔρmin = 0.33 e Å3
154 parameters
Crystal data top
C12H17N2S+·Cl·H2OV = 1404.56 (4) Å3
Mr = 274.81Z = 4
Monoclinic, P21/cCu Kα radiation
a = 13.4546 (2) ŵ = 3.69 mm1
b = 8.6547 (1) ÅT = 100 K
c = 12.7732 (2) Å0.44 × 0.25 × 0.14 mm
β = 109.210 (2)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer
2747 independent reflections
Absorption correction: numerical
(de Meulenaer & Tompa, 1965)
2509 reflections with I > 2.0σ(I)
Tmin = 0.30, Tmax = 0.61Rint = 0.029
19046 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.088H-atom parameters constrained
S = 1.02Δρmax = 0.43 e Å3
2509 reflectionsΔρmin = 0.33 e Å3
154 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.72343 (3)0.06408 (5)0.19253 (3)0.0234
C20.79732 (14)0.11421 (19)0.19970 (14)0.0244
C30.90751 (14)0.0827 (2)0.19854 (14)0.0252
C40.90283 (13)0.0099 (2)0.08935 (14)0.0244
N50.84522 (11)0.13793 (17)0.06888 (12)0.0225
C60.76970 (12)0.17936 (19)0.10687 (13)0.0199
N70.72435 (11)0.31807 (16)0.08222 (11)0.0217
C80.65460 (13)0.37922 (18)0.13689 (14)0.0210
C90.69975 (13)0.4718 (2)0.23077 (14)0.0224
C100.63438 (14)0.5346 (2)0.28445 (15)0.0278
C110.52719 (15)0.5046 (2)0.24466 (17)0.0319
C120.48404 (14)0.4128 (2)0.15214 (17)0.0300
C130.54694 (13)0.3482 (2)0.09525 (15)0.0255
C140.49879 (15)0.2481 (2)0.00495 (16)0.0319
C150.81647 (13)0.4980 (2)0.27462 (14)0.0249
Cl160.18401 (3)0.10294 (5)0.51765 (3)0.0238
O170.94136 (9)0.31268 (14)0.05720 (10)0.0272
H210.80120.16440.26780.0280*
H310.94500.18030.20670.0276*
H320.94320.01450.25730.0277*
H410.97480.01010.09080.0289*
H420.86940.08040.03000.0289*
H1410.43120.28850.04880.0475*
H1420.54260.24140.05100.0467*
H1430.48890.14500.01890.0475*
H1510.83320.57240.33390.0357*
H1520.84150.53570.21740.0356*
H1530.85150.40170.30300.0359*
H1710.91240.39660.05700.0391*
H1721.00560.32860.03350.0395*
H220.76040.17940.13790.0278*
H50.86670.20660.03180.0267*
H70.74660.38120.04170.0250*
H100.66350.59600.34740.0320*
H110.48380.54830.28250.0362*
H120.41110.39330.12550.0341*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0236 (2)0.0216 (2)0.0306 (2)0.00450 (15)0.01642 (17)0.00271 (14)
C20.0292 (9)0.0208 (8)0.0269 (8)0.0023 (6)0.0143 (7)0.0055 (6)
C30.0257 (8)0.0265 (8)0.0251 (8)0.0001 (7)0.0109 (7)0.0059 (7)
C40.0227 (8)0.0262 (9)0.0274 (8)0.0012 (7)0.0127 (7)0.0037 (6)
N50.0227 (7)0.0222 (7)0.0268 (7)0.0015 (5)0.0137 (5)0.0004 (5)
C60.0186 (7)0.0218 (8)0.0203 (7)0.0012 (6)0.0076 (6)0.0019 (6)
N70.0237 (7)0.0206 (7)0.0245 (7)0.0018 (5)0.0130 (6)0.0002 (5)
C80.0203 (7)0.0193 (8)0.0258 (8)0.0046 (6)0.0107 (6)0.0032 (6)
C90.0225 (8)0.0204 (8)0.0258 (8)0.0035 (6)0.0103 (7)0.0035 (6)
C100.0297 (9)0.0274 (8)0.0296 (9)0.0003 (7)0.0140 (7)0.0043 (7)
C110.0274 (9)0.0319 (10)0.0432 (10)0.0024 (8)0.0209 (8)0.0065 (7)
C120.0181 (8)0.0290 (9)0.0442 (11)0.0072 (8)0.0121 (7)0.0020 (7)
C130.0221 (8)0.0218 (8)0.0319 (9)0.0052 (7)0.0078 (7)0.0008 (6)
C140.0264 (8)0.0263 (9)0.0382 (10)0.0001 (8)0.0042 (7)0.0029 (7)
C150.0224 (8)0.0254 (9)0.0259 (8)0.0012 (7)0.0065 (7)0.0007 (6)
Cl160.0232 (2)0.0239 (2)0.0266 (2)0.00033 (14)0.01150 (16)0.00127 (14)
O170.0244 (6)0.0248 (6)0.0351 (7)0.0025 (5)0.0135 (5)0.0028 (5)
Geometric parameters (Å, º) top
S1—C21.8215 (17)C9—C101.391 (2)
S1—C61.7403 (16)C9—C151.501 (2)
C2—C31.512 (2)C10—C111.387 (3)
C2—H210.959C10—H100.936
C2—H220.964C11—C121.383 (3)
C3—C41.513 (2)C11—H110.950
C3—H310.971C12—C131.401 (3)
C3—H320.952C12—H120.942
C4—N51.474 (2)C13—C141.504 (3)
C4—H410.977C14—H1410.964
C4—H420.961C14—H1420.961
N5—C61.312 (2)C14—H1430.966
N5—H50.866C15—H1510.963
C6—N71.336 (2)C15—H1520.957
N7—C81.442 (2)C15—H1530.967
N7—H70.870O17—H1710.825
C8—C91.404 (2)O17—H1720.829
C8—C131.395 (2)
C2—S1—C6102.42 (8)C9—C8—C13122.61 (15)
S1—C2—C3111.57 (12)C8—C9—C10118.55 (16)
S1—C2—H21107.2C8—C9—C15120.71 (15)
C3—C2—H21109.3C10—C9—C15120.71 (16)
S1—C2—H22109.2C9—C10—C11119.76 (17)
C3—C2—H22109.9C9—C10—H10119.4
H21—C2—H22109.7C11—C10—H10120.8
C2—C3—C4109.91 (14)C10—C11—C12120.93 (16)
C2—C3—H31108.6C10—C11—H11118.6
C4—C3—H31108.9C12—C11—H11120.5
C2—C3—H32110.3C11—C12—C13121.14 (16)
C4—C3—H32109.0C11—C12—H12120.4
H31—C3—H32110.2C13—C12—H12118.5
C3—C4—N5112.65 (13)C12—C13—C8117.01 (16)
C3—C4—H41108.4C12—C13—C14120.45 (16)
N5—C4—H41108.0C8—C13—C14122.53 (16)
C3—C4—H42109.2C13—C14—H141110.2
N5—C4—H42109.1C13—C14—H142112.1
H41—C4—H42109.3H141—C14—H142108.5
C4—N5—C6126.70 (14)C13—C14—H143109.2
C4—N5—H5116.2H141—C14—H143108.5
C6—N5—H5116.9H142—C14—H143108.3
S1—C6—N5123.83 (13)C9—C15—H151109.9
S1—C6—N7115.66 (12)C9—C15—H152110.8
N5—C6—N7120.50 (15)H151—C15—H152108.8
C6—N7—C8122.35 (13)C9—C15—H153109.3
C6—N7—H7118.9H151—C15—H153108.8
C8—N7—H7117.6H152—C15—H153109.3
N7—C8—C9117.10 (14)H171—O17—H172106.9
N7—C8—C13120.28 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···O170.871.972.815 (2)163
O17—H171···Cl16i0.822.363.158 (1)164
N7—H7···Cl16i0.872.373.204 (1)162
O17—H172···Cl16ii0.832.353.171 (1)173
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+1, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC12H17N2S+·Cl·H2O
Mr274.81
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)13.4546 (2), 8.6547 (1), 12.7732 (2)
β (°) 109.210 (2)
V3)1404.56 (4)
Z4
Radiation typeCu Kα
µ (mm1)3.69
Crystal size (mm)0.44 × 0.25 × 0.14
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer
Absorption correctionNumerical
(de Meulenaer & Tompa, 1965)
Tmin, Tmax0.30, 0.61
No. of measured, independent and
observed [I > 2.0σ(I)] reflections
19046, 2747, 2509
Rint0.029
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.088, 1.02
No. of reflections2509
No. of parameters154
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.43, 0.33

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···O170.871.972.815 (2)163
O17—H171···Cl16i0.822.363.158 (1)164
N7—H7···Cl16i0.872.373.204 (1)162
O17—H172···Cl16ii0.832.353.171 (1)173
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+1, y+1/2, z1/2.
 

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