In the title compound, alternatively called xylazine hydrochloride monohydrate, C
12H
17N
2S
+·Cl
−·H
2O, 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
CCDC reference: 667774
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(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
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.
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.
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).
N-(2,6-Dimethylanilino)-5,6-dihydro-4
H-1,3-thiazin-3-ium
chloride monohydrate
top
Crystal data top
C12H17N2S+·Cl−·H2O | F(000) = 584 |
Mr = 274.81 | Dx = 1.300 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -P 2ybc | Cell parameters from 19046 reflections |
a = 13.4546 (2) Å | θ = 3.5–74.6° |
b = 8.6547 (1) Å | µ = 3.69 mm−1 |
c = 12.7732 (2) Å | T = 100 K |
β = 109.210 (2)° | Prism, white |
V = 1404.56 (4) Å3 | 0.44 × 0.25 × 0.14 mm |
Z = 4 | |
Data collection top
Oxford Diffraction Xcalibur diffractometer | 2747 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 2509 reflections with I > 2.0σ(I) |
Graphite monochromator | Rint = 0.029 |
ϕ and ω scans | θmax = 74.6°, θmin = 3.5° |
Absorption correction: numerical (de Meulenaer & Tompa, 1965) | h = −16→16 |
Tmin = 0.30, Tmax = 0.61 | k = −10→10 |
19046 measured reflections | l = −15→15 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-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 = 1.02 | Δρmax = 0.43 e Å−3 |
2509 reflections | Δρmin = −0.33 e Å−3 |
154 parameters | |
Crystal data top
C12H17N2S+·Cl−·H2O | V = 1404.56 (4) Å3 |
Mr = 274.81 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 13.4546 (2) Å | µ = 3.69 mm−1 |
b = 8.6547 (1) Å | T = 100 K |
c = 12.7732 (2) Å | 0.44 × 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 = 0.61 | Rint = 0.029 |
19046 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.43 e Å−3 |
2509 reflections | Δρmin = −0.33 e Å−3 |
154 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.72343 (3) | 0.06408 (5) | 0.19253 (3) | 0.0234 | |
C2 | 0.79732 (14) | −0.11421 (19) | 0.19970 (14) | 0.0244 | |
C3 | 0.90751 (14) | −0.0827 (2) | 0.19854 (14) | 0.0252 | |
C4 | 0.90283 (13) | −0.0099 (2) | 0.08935 (14) | 0.0244 | |
N5 | 0.84522 (11) | 0.13793 (17) | 0.06888 (12) | 0.0225 | |
C6 | 0.76970 (12) | 0.17936 (19) | 0.10687 (13) | 0.0199 | |
N7 | 0.72435 (11) | 0.31807 (16) | 0.08222 (11) | 0.0217 | |
C8 | 0.65460 (13) | 0.37922 (18) | 0.13689 (14) | 0.0210 | |
C9 | 0.69975 (13) | 0.4718 (2) | 0.23077 (14) | 0.0224 | |
C10 | 0.63438 (14) | 0.5346 (2) | 0.28445 (15) | 0.0278 | |
C11 | 0.52719 (15) | 0.5046 (2) | 0.24466 (17) | 0.0319 | |
C12 | 0.48404 (14) | 0.4128 (2) | 0.15214 (17) | 0.0300 | |
C13 | 0.54694 (13) | 0.3482 (2) | 0.09525 (15) | 0.0255 | |
C14 | 0.49879 (15) | 0.2481 (2) | −0.00495 (16) | 0.0319 | |
C15 | 0.81647 (13) | 0.4980 (2) | 0.27462 (14) | 0.0249 | |
Cl16 | 0.18401 (3) | 0.10294 (5) | 0.51765 (3) | 0.0238 | |
O17 | 0.94136 (9) | 0.31268 (14) | −0.05720 (10) | 0.0272 | |
H21 | 0.8012 | −0.1644 | 0.2678 | 0.0280* | |
H31 | 0.9450 | −0.1803 | 0.2067 | 0.0276* | |
H32 | 0.9432 | −0.0145 | 0.2573 | 0.0277* | |
H41 | 0.9748 | 0.0101 | 0.0908 | 0.0289* | |
H42 | 0.8694 | −0.0804 | 0.0300 | 0.0289* | |
H141 | 0.4312 | 0.2885 | −0.0488 | 0.0475* | |
H142 | 0.5426 | 0.2414 | −0.0510 | 0.0467* | |
H143 | 0.4889 | 0.1450 | 0.0189 | 0.0475* | |
H151 | 0.8332 | 0.5724 | 0.3339 | 0.0357* | |
H152 | 0.8415 | 0.5357 | 0.2174 | 0.0356* | |
H153 | 0.8515 | 0.4017 | 0.3030 | 0.0359* | |
H171 | 0.9124 | 0.3966 | −0.0570 | 0.0391* | |
H172 | 1.0056 | 0.3286 | −0.0335 | 0.0395* | |
H22 | 0.7604 | −0.1794 | 0.1379 | 0.0278* | |
H5 | 0.8667 | 0.2066 | 0.0318 | 0.0267* | |
H7 | 0.7466 | 0.3812 | 0.0417 | 0.0250* | |
H10 | 0.6635 | 0.5960 | 0.3474 | 0.0320* | |
H11 | 0.4838 | 0.5483 | 0.2825 | 0.0362* | |
H12 | 0.4111 | 0.3933 | 0.1255 | 0.0341* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0236 (2) | 0.0216 (2) | 0.0306 (2) | 0.00450 (15) | 0.01642 (17) | 0.00271 (14) |
C2 | 0.0292 (9) | 0.0208 (8) | 0.0269 (8) | 0.0023 (6) | 0.0143 (7) | 0.0055 (6) |
C3 | 0.0257 (8) | 0.0265 (8) | 0.0251 (8) | −0.0001 (7) | 0.0109 (7) | 0.0059 (7) |
C4 | 0.0227 (8) | 0.0262 (9) | 0.0274 (8) | −0.0012 (7) | 0.0127 (7) | 0.0037 (6) |
N5 | 0.0227 (7) | 0.0222 (7) | 0.0268 (7) | 0.0015 (5) | 0.0137 (5) | 0.0004 (5) |
C6 | 0.0186 (7) | 0.0218 (8) | 0.0203 (7) | −0.0012 (6) | 0.0076 (6) | −0.0019 (6) |
N7 | 0.0237 (7) | 0.0206 (7) | 0.0245 (7) | 0.0018 (5) | 0.0130 (6) | 0.0002 (5) |
C8 | 0.0203 (7) | 0.0193 (8) | 0.0258 (8) | 0.0046 (6) | 0.0107 (6) | 0.0032 (6) |
C9 | 0.0225 (8) | 0.0204 (8) | 0.0258 (8) | 0.0035 (6) | 0.0103 (7) | 0.0035 (6) |
C10 | 0.0297 (9) | 0.0274 (8) | 0.0296 (9) | −0.0003 (7) | 0.0140 (7) | 0.0043 (7) |
C11 | 0.0274 (9) | 0.0319 (10) | 0.0432 (10) | 0.0024 (8) | 0.0209 (8) | 0.0065 (7) |
C12 | 0.0181 (8) | 0.0290 (9) | 0.0442 (11) | 0.0072 (8) | 0.0121 (7) | 0.0020 (7) |
C13 | 0.0221 (8) | 0.0218 (8) | 0.0319 (9) | 0.0052 (7) | 0.0078 (7) | 0.0008 (6) |
C14 | 0.0264 (8) | 0.0263 (9) | 0.0382 (10) | 0.0001 (8) | 0.0042 (7) | −0.0029 (7) |
C15 | 0.0224 (8) | 0.0254 (9) | 0.0259 (8) | 0.0012 (7) | 0.0065 (7) | 0.0007 (6) |
Cl16 | 0.0232 (2) | 0.0239 (2) | 0.0266 (2) | 0.00033 (14) | 0.01150 (16) | 0.00127 (14) |
O17 | 0.0244 (6) | 0.0248 (6) | 0.0351 (7) | −0.0025 (5) | 0.0135 (5) | −0.0028 (5) |
Geometric parameters (Å, º) top
S1—C2 | 1.8215 (17) | C9—C10 | 1.391 (2) |
S1—C6 | 1.7403 (16) | C9—C15 | 1.501 (2) |
C2—C3 | 1.512 (2) | C10—C11 | 1.387 (3) |
C2—H21 | 0.959 | C10—H10 | 0.936 |
C2—H22 | 0.964 | C11—C12 | 1.383 (3) |
C3—C4 | 1.513 (2) | C11—H11 | 0.950 |
C3—H31 | 0.971 | C12—C13 | 1.401 (3) |
C3—H32 | 0.952 | C12—H12 | 0.942 |
C4—N5 | 1.474 (2) | C13—C14 | 1.504 (3) |
C4—H41 | 0.977 | C14—H141 | 0.964 |
C4—H42 | 0.961 | C14—H142 | 0.961 |
N5—C6 | 1.312 (2) | C14—H143 | 0.966 |
N5—H5 | 0.866 | C15—H151 | 0.963 |
C6—N7 | 1.336 (2) | C15—H152 | 0.957 |
N7—C8 | 1.442 (2) | C15—H153 | 0.967 |
N7—H7 | 0.870 | O17—H171 | 0.825 |
C8—C9 | 1.404 (2) | O17—H172 | 0.829 |
C8—C13 | 1.395 (2) | | |
| | | |
C2—S1—C6 | 102.42 (8) | C9—C8—C13 | 122.61 (15) |
S1—C2—C3 | 111.57 (12) | C8—C9—C10 | 118.55 (16) |
S1—C2—H21 | 107.2 | C8—C9—C15 | 120.71 (15) |
C3—C2—H21 | 109.3 | C10—C9—C15 | 120.71 (16) |
S1—C2—H22 | 109.2 | C9—C10—C11 | 119.76 (17) |
C3—C2—H22 | 109.9 | C9—C10—H10 | 119.4 |
H21—C2—H22 | 109.7 | C11—C10—H10 | 120.8 |
C2—C3—C4 | 109.91 (14) | C10—C11—C12 | 120.93 (16) |
C2—C3—H31 | 108.6 | C10—C11—H11 | 118.6 |
C4—C3—H31 | 108.9 | C12—C11—H11 | 120.5 |
C2—C3—H32 | 110.3 | C11—C12—C13 | 121.14 (16) |
C4—C3—H32 | 109.0 | C11—C12—H12 | 120.4 |
H31—C3—H32 | 110.2 | C13—C12—H12 | 118.5 |
C3—C4—N5 | 112.65 (13) | C12—C13—C8 | 117.01 (16) |
C3—C4—H41 | 108.4 | C12—C13—C14 | 120.45 (16) |
N5—C4—H41 | 108.0 | C8—C13—C14 | 122.53 (16) |
C3—C4—H42 | 109.2 | C13—C14—H141 | 110.2 |
N5—C4—H42 | 109.1 | C13—C14—H142 | 112.1 |
H41—C4—H42 | 109.3 | H141—C14—H142 | 108.5 |
C4—N5—C6 | 126.70 (14) | C13—C14—H143 | 109.2 |
C4—N5—H5 | 116.2 | H141—C14—H143 | 108.5 |
C6—N5—H5 | 116.9 | H142—C14—H143 | 108.3 |
S1—C6—N5 | 123.83 (13) | C9—C15—H151 | 109.9 |
S1—C6—N7 | 115.66 (12) | C9—C15—H152 | 110.8 |
N5—C6—N7 | 120.50 (15) | H151—C15—H152 | 108.8 |
C6—N7—C8 | 122.35 (13) | C9—C15—H153 | 109.3 |
C6—N7—H7 | 118.9 | H151—C15—H153 | 108.8 |
C8—N7—H7 | 117.6 | H152—C15—H153 | 109.3 |
N7—C8—C9 | 117.10 (14) | H171—O17—H172 | 106.9 |
N7—C8—C13 | 120.28 (15) | | |
Hydrogen-bond geometry (Å, º) top
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 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1, −y+1/2, z−1/2. |
Experimental details
Crystal data |
Chemical formula | C12H17N2S+·Cl−·H2O |
Mr | 274.81 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 13.4546 (2), 8.6547 (1), 12.7732 (2) |
β (°) | 109.210 (2) |
V (Å3) | 1404.56 (4) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 3.69 |
Crystal size (mm) | 0.44 × 0.25 × 0.14 |
|
Data collection |
Diffractometer | Oxford Diffraction Xcalibur diffractometer |
Absorption correction | Numerical (de Meulenaer & Tompa, 1965) |
Tmin, Tmax | 0.30, 0.61 |
No. of measured, independent and observed [I > 2.0σ(I)] reflections | 19046, 2747, 2509 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.625 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.088, 1.02 |
No. of reflections | 2509 |
No. of parameters | 154 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.43, −0.33 |
Hydrogen-bond geometry (Å, º) top
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 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1, −y+1/2, z−1/2. |
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.