Crystal structure of 2-amino-5-methyl­sulfanyl-1,3,4-thia­diazol-3-ium chloride monohydrate

Soudani, S.; Aubert, E.; Jelsch, C.; Ben Nasr, C.

doi:10.1107/S1600536814015864

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o913-o914

doi:10.1107/S1600536814015864

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Crystal structure of 2-amino-5-methylsulfanyl-1,3,4-thiadiazol-3-ium chloride monohydrate

Sarra Soudani,^a Emmanuel Aubert,^b Christian Jelsch ^b and Cherif Ben Nasr ^a ^*

^aLaboratoire de Chimie des Matériaux, Faculté des sciences de Bizerte, 7021 Zarzouna, Tunisia, and ^bCristallographie, Résonance Magnétique et Modélisations (CRM2), UMR CNRS–UHP 7036, Institut Jean Barriol, Université de Lorraine, BP 70239, Boulevard des Aiguillettes, 54506 Vandoeuvre-les-Nancy, France
^*Correspondence e-mail: cherif_bennasr@yahoo.fr

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 30 June 2014; accepted 8 July 2014; online 1 August 2014)

The title salt, C₃H₆N₃S₂⁺·Cl⁻·H₂O, crystallized with two organic cations, two chloride anions and two water molecules in the asymmetric unit. The methyl C atoms deviate from their respective bound ring planes by 0.081 and 0.002 Å. In the crystal, the components are connected via N—H⋯O, N—H⋯Cl and O—H⋯Cl hydrogen bonds, forming sheets lying parallel to (100). The sheets are linked into bilayers by O—H⋯Cl hydrogen bonds involving the chloride ions and water molecules. Within the bilayers there are π–π interactions [inter-centroid distances = 3.4654 (4) and 3.4789 (4) Å] involving inversion-related cations.

Keywords: crystal structure; 1,3,4-thiadiazole; biological activity; organic-inorganic hybrid.

CCDC reference: 1012703

1. Related literature

For the medicinal importance and biological activity of thiadiazol isomers, see: Demirbas et al. (2009 ). For applications of 1,3,4 thiadiazoles in agriculture, see: Wei et al. (2006 ). For C—N bond lengths in the 2-amino-5-methylsulfanyl-1,3,4-thiadiazol-3-ium cation, see: Mrad et al. (2012 ).

2. Experimental

2.1. Crystal data

C₃H₆N₃S₂⁺·Cl⁻·H₂O
M_r = 201.69
Monoclinic, P 2/n
a = 13.3826 (2) Å
b = 9.4258 (1) Å
c = 13.5762 (2) Å
β = 99.453 (1)°
V = 1689.27 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.89 mm⁻¹
T = 110 K
0.42 × 0.31 × 0.15 mm

2.2. Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012 ), using a multi-faceted crystal model based on expressions derived by Clark & Reid (1995 )] T_min = 0.769, T_max = 0.894
65950 measured reflections
8394 independent reflections
7745 reflections with I > 2σ(I)
R_int = 0.021

2.3. Refinement

R[F² > 2σ(F²)] = 0.020
wR(F²) = 0.054
S = 1.12
8394 reflections
224 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O17	0.861 (13)	1.818 (13)	2.6778 (7)	176.4 (12)
N6—H6A⋯Cl1	0.846 (12)	2.296 (12)	3.1178 (6)	164.2 (11)
N6—H6B⋯Cl2ⁱ	0.829 (13)	2.392 (13)	3.2139 (7)	171.4 (13)
N11—H11⋯O18	0.914 (14)	1.751 (14)	2.6632 (7)	176.7 (13)
N14—H14A⋯Cl2	0.877 (12)	2.289 (12)	3.1287 (6)	160.3 (11)
N14—H14B⋯Cl1ⁱⁱ	0.807 (13)	2.461 (13)	3.2648 (6)	173.6 (13)
O17—H17A⋯Cl2ⁱ	0.796 (14)	2.373 (14)	3.1593 (5)	169.8 (14)
O17—H17B⋯Cl2ⁱⁱⁱ	0.826 (15)	2.340 (15)	3.1649 (6)	175.5 (14)
O18—H18A⋯Cl1ⁱⁱ	0.780 (13)	2.414 (13)	3.1708 (5)	163.8 (13)
O18—H18B⋯Cl1^iv	0.837 (15)	2.318 (15)	3.1517 (6)	174.1 (14)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-1, -z+{\script{3\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1012703

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814015864/su2749sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814015864/su2749Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814015864/su2749Isup3.tif

Supporting information file. DOI: 10.1107/S1600536814015864/su2749Isup4.cml

checkCIF report

Chemical context top

The amine under investigation, 2-amino-5-(methylthio)-1,3,4-thiadiazole, belongs to the larger family of heterocyclic compounds with potential medicinal importance and broad spectra of biological activities. Among these types of organic molecules are several isomers of thiadiazole (Demirbas et al., 2009). 1,3,4-thiadiazoles represent one of the most biologically active classes of compounds with a wide spectrum of activities. A large number of 1,3,4-thiadiazoles have been patented in the agricultural field as herbicides and bactericides (Wei et al., 2006). In the present investigation, we report the synthesis and crystal structure of a new organic-inorganic hybrid compound prepared from the reaction of the title amine with the hydrochloric acid in aqueous medium.

Structural commentary top

As shown in Fig. 1, the asymmetric unit of the title compound contains two 2-amino-5-(methylthio)-1,3,4-thiadiazol-3-ium cations, two chloride anions and two water molecules. These entities are connected by N—H···Cl, N—H···O and O—H···Cl hydrogen bonds, forming sheets parallel to (100) (Table 1 and Fig. 2). The layers are connect through O—H···Cl contacts, forming bilayers (Figs. 2 and 3).

Examination of the geometrical features of the organic cations shows that the exocyclic C—N bond lengths are similar in length to those of the thiadiazole rings, probably due to delocalization of the ring π density with the p-orbital electrons of the amino group. These C—N distances, ca. 1.33 Å, are compatible to that of [C₃H₆N₃S₂]H₂PO₄ which contains the same organic entity (Mrad et al., 2012).

Supramolecular features top

The crystal packing is also influenced by intermolecular π–π stacking interactions between inversion-related anti-parallel organic cations within the bilayers (Fig. 3); Cg1···Cg1ⁱ = 3.4654 (4) Å [Cg1 is the centroid of the S1/N3/N4/C2/C5 ring; symmetry code: (i) -x, -y+2, -z+1] and Cg2···Cg2ⁱⁱ = 3.4789 (4) Å [Cg2 is the centroid of the S9/N11/N12/C10/C13 ring; symmetry code: -x+1, -y+1, -z+1].

Synthesis and crystallization top

An aqueous 1 M HCl solution and 2-amino-5-(methylthio)-1,3,4-thiadiazole in a 1:1 molar ratio were mixed and dissolved in sufficient ethanol. Crystals of the title salt grew as the ethanol evaporated at room temperature over the course of a few days.

Refinement top

The N- and O-bound H atoms were located in difference Fourier maps and freely refined. The C-bound H atoms were included in calculated positions and treated as riding atoms: C—H = 0.98 Å with U_iso(H) = 1.2Ueq(C). Experimental details are given in Table 2.

Related literature top

For the medicinal importance and biological activity of thiadiazol isomers, see: Demirbas et al. (2009). For applications of 1,3,4 thiadiazoles in agriculture, see: Wei et al. (2006). For C—N bond lengths in the 2-amino-5-methylsulfanyl-1,3,4-thiadiazol-3-ium cation, see: Mrad et al. (2012).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of molecular structure of the title salt, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view along the b axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1 for details).
	Fig. 3. A partial view along the b axis of the crystal packing of the title compound, showing the intermolecular π–π stacking interactions between inversion-related organic cations.

2-Amino-5-methylsulfanyl-1,3,4-thiadiazol-3-ium chloride monohydrate top

Crystal data top

C₃H₆N₃S₂⁺·Cl⁻·H₂O	F(000) = 832
M_r = 201.69	D_x = 1.586 Mg m⁻³
Monoclinic, P2/n	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2yac	Cell parameters from 30742 reflections
a = 13.3826 (2) Å	θ = 2.9–37.8°
b = 9.4258 (1) Å	µ = 0.89 mm⁻¹
c = 13.5762 (2) Å	T = 110 K
β = 99.453 (1)°	Prism, colorless
V = 1689.27 (4) Å³	0.42 × 0.31 × 0.15 mm
Z = 8

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	8394 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	7745 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.021
Detector resolution: 10.4508 pixels mm^-1	θ_max = 36.7°, θ_min = 2.9°
ω scans	h = −22→22
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012), using a multi-faceted crystal model based on expressions derived by Clark & Reid (1995)]	k = −15→15
T_min = 0.769, T_max = 0.894	l = −22→22
65950 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.020	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.054	w = 1/[σ²(F_o²) + (0.0211P)² + 0.370P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max = 0.003
8394 reflections	Δρ_max = 0.47 e Å⁻³
224 parameters	Δρ_min = −0.28 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00111 (13)

Crystal data top

C₃H₆N₃S₂⁺·Cl⁻·H₂O	V = 1689.27 (4) Å³
M_r = 201.69	Z = 8
Monoclinic, P2/n	Mo Kα radiation
a = 13.3826 (2) Å	µ = 0.89 mm⁻¹
b = 9.4258 (1) Å	T = 110 K
c = 13.5762 (2) Å	0.42 × 0.31 × 0.15 mm
β = 99.453 (1)°

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	8394 independent reflections
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012), using a multi-faceted crystal model based on expressions derived by Clark & Reid (1995)]	7745 reflections with I > 2σ(I)
T_min = 0.769, T_max = 0.894	R_int = 0.021
65950 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	0 restraints
wR(F²) = 0.054	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.47 e Å⁻³
8394 reflections	Δρ_min = −0.28 e Å⁻³
224 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S7	0.127439 (13)	1.268596 (18)	0.444671 (12)	0.01782 (3)
Cl2	0.386288 (13)	0.472130 (17)	0.838806 (12)	0.01897 (3)
S1	0.129775 (12)	1.086700 (17)	0.628112 (12)	0.01498 (3)
S9	0.353350 (12)	0.596116 (17)	0.572019 (12)	0.01549 (3)
S15	0.370685 (15)	0.777122 (18)	0.392656 (13)	0.02012 (3)
Cl1	0.112933 (13)	0.978631 (17)	0.878768 (12)	0.01911 (3)
O18	0.39361 (4)	0.11409 (5)	0.40860 (4)	0.01921 (9)
O17	0.10727 (4)	0.60603 (5)	0.44691 (4)	0.01852 (9)
N12	0.38085 (4)	0.49199 (6)	0.40204 (4)	0.01616 (9)
N3	0.12906 (4)	0.87190 (6)	0.51663 (4)	0.01608 (9)
N6	0.13116 (5)	0.81093 (7)	0.68457 (4)	0.01909 (10)
N11	0.37722 (4)	0.38126 (6)	0.46775 (4)	0.01566 (9)
N14	0.35554 (5)	0.32153 (6)	0.63065 (4)	0.01771 (9)
N4	0.12853 (4)	0.98357 (6)	0.45103 (4)	0.01622 (9)
C10	0.36248 (5)	0.41383 (6)	0.55932 (5)	0.01406 (9)
C5	0.12929 (5)	1.10218 (7)	0.49890 (5)	0.01482 (9)
C13	0.36960 (5)	0.61102 (7)	0.44630 (5)	0.01494 (10)
C2	0.13012 (5)	0.90405 (7)	0.61203 (5)	0.01490 (10)
C16	0.38878 (6)	0.72871 (9)	0.26821 (5)	0.02396 (13)
H16B	0.4528	0.6771	0.2715	0.036*
H16A	0.3906	0.8146	0.2279	0.036*
H16C	0.3327	0.6681	0.2376	0.036*
C8	0.13379 (6)	1.21799 (9)	0.31782 (5)	0.02475 (13)
H8B	0.1962	1.1643	0.3161	0.037*
H8A	0.1335	1.3033	0.2765	0.037*
H8C	0.0751	1.1589	0.2919	0.037*
H18B	0.4504 (11)	0.0902 (15)	0.3960 (11)	0.045 (4)*
H18A	0.3831 (10)	0.0703 (14)	0.4546 (10)	0.033 (3)*
H6A	0.1303 (9)	0.8410 (13)	0.7431 (9)	0.028 (3)*
H14B	0.3640 (10)	0.2376 (14)	0.6235 (10)	0.033 (3)*
H14A	0.3506 (9)	0.3519 (14)	0.6907 (9)	0.031 (3)*
H6B	0.1286 (10)	0.7247 (14)	0.6724 (10)	0.036 (3)*
H17B	0.0504 (11)	0.5876 (15)	0.4157 (11)	0.045 (4)*
H17A	0.1117 (10)	0.5630 (15)	0.4979 (10)	0.037 (3)*
H3	0.1242 (9)	0.7870 (14)	0.4929 (9)	0.033 (3)*
H11	0.3851 (10)	0.2905 (15)	0.4467 (10)	0.043 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S7	0.02231 (7)	0.01564 (6)	0.01558 (6)	−0.00113 (5)	0.00333 (5)	−0.00038 (5)
Cl2	0.02398 (7)	0.01862 (7)	0.01352 (6)	0.00121 (5)	0.00077 (5)	−0.00314 (5)
S1	0.01744 (6)	0.01459 (6)	0.01294 (6)	−0.00041 (5)	0.00259 (5)	−0.00314 (5)
S9	0.01931 (7)	0.01389 (6)	0.01357 (6)	0.00047 (5)	0.00357 (5)	−0.00272 (5)
S15	0.02861 (8)	0.01529 (7)	0.01681 (7)	−0.00147 (6)	0.00476 (6)	0.00022 (5)
Cl1	0.02353 (7)	0.01790 (6)	0.01740 (6)	−0.00308 (5)	0.00778 (5)	−0.00374 (5)
O18	0.0268 (2)	0.01509 (19)	0.0167 (2)	0.00361 (17)	0.00633 (18)	0.00171 (16)
O17	0.0251 (2)	0.0155 (2)	0.01450 (19)	−0.00279 (17)	0.00197 (17)	0.00079 (15)
N12	0.0187 (2)	0.0157 (2)	0.0147 (2)	−0.00090 (17)	0.00432 (17)	−0.00181 (17)
N3	0.0205 (2)	0.0144 (2)	0.0132 (2)	−0.00115 (17)	0.00220 (17)	−0.00289 (16)
N6	0.0265 (3)	0.0163 (2)	0.0143 (2)	−0.0013 (2)	0.00311 (19)	−0.00122 (18)
N11	0.0194 (2)	0.0141 (2)	0.0139 (2)	−0.00025 (17)	0.00404 (17)	−0.00234 (16)
N14	0.0241 (2)	0.0152 (2)	0.0137 (2)	0.00121 (19)	0.00275 (18)	−0.00082 (17)
N4	0.0190 (2)	0.0158 (2)	0.0137 (2)	−0.00094 (17)	0.00235 (17)	−0.00223 (17)
C10	0.0144 (2)	0.0141 (2)	0.0135 (2)	0.00004 (17)	0.00170 (18)	−0.00237 (17)
C5	0.0149 (2)	0.0160 (2)	0.0135 (2)	−0.00038 (18)	0.00204 (18)	−0.00209 (18)
C13	0.0159 (2)	0.0150 (2)	0.0140 (2)	−0.00095 (18)	0.00286 (18)	−0.00155 (18)
C2	0.0153 (2)	0.0154 (2)	0.0139 (2)	−0.00111 (18)	0.00202 (18)	−0.00291 (18)
C16	0.0260 (3)	0.0305 (4)	0.0159 (3)	0.0014 (3)	0.0047 (2)	0.0019 (2)
C8	0.0297 (3)	0.0296 (4)	0.0161 (3)	−0.0003 (3)	0.0069 (2)	0.0003 (2)

Geometric parameters (Å, º) top

S7—C5	1.7312 (7)	N3—H3	0.861 (13)
S7—C8	1.8024 (7)	N6—C2	1.3176 (9)
S1—C2	1.7355 (6)	N6—H6A	0.846 (12)
S1—C5	1.7593 (6)	N6—H6B	0.829 (13)
S9—C10	1.7331 (6)	N11—C10	1.3264 (8)
S9—C13	1.7613 (6)	N11—H11	0.913 (14)
S15—C13	1.7278 (7)	N14—C10	1.3164 (9)
S15—C16	1.8043 (8)	N14—H14B	0.808 (13)
O18—H18B	0.836 (15)	N14—H14A	0.876 (13)
O18—H18A	0.780 (14)	N4—C5	1.2923 (8)
O17—H17B	0.827 (15)	C16—H16B	0.9800
O17—H17A	0.796 (14)	C16—H16A	0.9800
N12—C13	1.2932 (8)	C16—H16C	0.9800
N12—N11	1.3791 (8)	C8—H8B	0.9800
N3—C2	1.3280 (8)	C8—H8A	0.9800
N3—N4	1.3781 (8)	C8—H8C	0.9800

C5—S7—C8	99.61 (3)	N11—C10—S9	110.27 (5)
C2—S1—C5	87.51 (3)	N4—C5—S7	124.86 (5)
C10—S9—C13	87.75 (3)	N4—C5—S1	115.35 (5)
C13—S15—C16	100.21 (3)	S7—C5—S1	119.78 (4)
H18B—O18—H18A	108.1 (13)	N12—C13—S15	125.50 (5)
H17B—O17—H17A	105.6 (13)	N12—C13—S9	115.05 (5)
C13—N12—N11	109.69 (5)	S15—C13—S9	119.45 (4)
C2—N3—N4	117.01 (5)	N6—C2—N3	125.04 (6)
C2—N3—H3	124.4 (8)	N6—C2—S1	124.52 (5)
N4—N3—H3	118.4 (8)	N3—C2—S1	110.44 (5)
C2—N6—H6A	118.6 (8)	S15—C16—H16B	109.5
C2—N6—H6B	120.6 (9)	S15—C16—H16A	109.5
H6A—N6—H6B	120.6 (12)	H16B—C16—H16A	109.5
C10—N11—N12	117.23 (5)	S15—C16—H16C	109.5
C10—N11—H11	123.5 (9)	H16B—C16—H16C	109.5
N12—N11—H11	119.3 (9)	H16A—C16—H16C	109.5
C10—N14—H14B	122.1 (9)	S7—C8—H8B	109.5
C10—N14—H14A	119.6 (8)	S7—C8—H8A	109.5
H14B—N14—H14A	117.7 (12)	H8B—C8—H8A	109.5
C5—N4—N3	109.70 (5)	S7—C8—H8C	109.5
N14—C10—N11	125.16 (6)	H8B—C8—H8C	109.5
N14—C10—S9	124.57 (5)	H8A—C8—H8C	109.5

C13—N12—N11—C10	0.74 (8)	C2—S1—C5—S7	179.35 (4)
C2—N3—N4—C5	0.04 (8)	N11—N12—C13—S15	179.19 (5)
N12—N11—C10—N14	178.94 (6)	N11—N12—C13—S9	−0.16 (7)
N12—N11—C10—S9	−0.95 (7)	C16—S15—C13—N12	0.81 (7)
C13—S9—C10—N14	−179.23 (6)	C16—S15—C13—S9	−179.87 (4)
C13—S9—C10—N11	0.67 (5)	C10—S9—C13—N12	−0.29 (5)
N3—N4—C5—S7	−179.17 (5)	C10—S9—C13—S15	−179.68 (4)
N3—N4—C5—S1	−0.44 (7)	N4—N3—C2—N6	−179.72 (6)
C8—S7—C5—N4	−3.94 (7)	N4—N3—C2—S1	0.37 (7)
C8—S7—C5—S1	177.38 (4)	C5—S1—C2—N6	179.60 (6)
C2—S1—C5—N4	0.55 (5)	C5—S1—C2—N3	−0.49 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O17	0.861 (13)	1.818 (13)	2.6778 (7)	176.4 (12)
N6—H6A···Cl1	0.846 (12)	2.296 (12)	3.1178 (6)	164.2 (11)
N6—H6B···Cl2ⁱ	0.829 (13)	2.392 (13)	3.2139 (7)	171.4 (13)
N11—H11···O18	0.914 (14)	1.751 (14)	2.6632 (7)	176.7 (13)
N14—H14A···Cl2	0.877 (12)	2.289 (12)	3.1287 (6)	160.3 (11)
N14—H14B···Cl1ⁱⁱ	0.807 (13)	2.461 (13)	3.2648 (6)	173.6 (13)
O17—H17A···Cl2ⁱ	0.796 (14)	2.373 (14)	3.1593 (5)	169.8 (14)
O17—H17B···Cl2ⁱⁱⁱ	0.826 (15)	2.340 (15)	3.1649 (6)	175.5 (14)
O18—H18A···Cl1ⁱⁱ	0.780 (13)	2.414 (13)	3.1708 (5)	163.8 (13)
O18—H18B···Cl1^iv	0.837 (15)	2.318 (15)	3.1517 (6)	174.1 (14)

Symmetry codes: (i) −x+1/2, y, −z+3/2; (ii) −x+1/2, y−1, −z+3/2; (iii) x−1/2, −y+1, z−1/2; (iv) x+1/2, −y+1, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O17	0.861 (13)	1.818 (13)	2.6778 (7)	176.4 (12)
N6—H6A···Cl1	0.846 (12)	2.296 (12)	3.1178 (6)	164.2 (11)
N6—H6B···Cl2ⁱ	0.829 (13)	2.392 (13)	3.2139 (7)	171.4 (13)
N11—H11···O18	0.914 (14)	1.751 (14)	2.6632 (7)	176.7 (13)
N14—H14A···Cl2	0.877 (12)	2.289 (12)	3.1287 (6)	160.3 (11)
N14—H14B···Cl1ⁱⁱ	0.807 (13)	2.461 (13)	3.2648 (6)	173.6 (13)
O17—H17A···Cl2ⁱ	0.796 (14)	2.373 (14)	3.1593 (5)	169.8 (14)
O17—H17B···Cl2ⁱⁱⁱ	0.826 (15)	2.340 (15)	3.1649 (6)	175.5 (14)
O18—H18A···Cl1ⁱⁱ	0.780 (13)	2.414 (13)	3.1708 (5)	163.8 (13)
O18—H18B···Cl1^iv	0.837 (15)	2.318 (15)	3.1517 (6)	174.1 (14)

Symmetry codes: (i) −x+1/2, y, −z+3/2; (ii) −x+1/2, y−1, −z+3/2; (iii) x−1/2, −y+1, z−1/2; (iv) x+1/2, −y+1, z−1/2.

Acknowledgements

We are most grateful for the support provided by the Secretary of State for Scientific Research and Technology of Tunisia, and the DRX service of the University of Lorraine, France.

References

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Volume 70| Part 9| September 2014| Pages o913-o914

doi:10.1107/S1600536814015864

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 2-amino-5-methyl­sulfanyl-1,3,4-thia­diazol-3-ium chloride monohydrate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 2-amino-5-methylsulfanyl-1,3,4-thiadiazol-3-ium chloride monohydrate