2-Amino-5-ethoxy-carbonyl-4-methyl-thia-zol-3-ium chloride monohydrate.

In the crystal structure of the title compound, C(7)H(11)N(2)O(2)S(+)·Cl(-)·H(2)O, the cations, anions and water mol-ecules are linked by inter-molecular N-H⋯O, N-H⋯Cl, O-H⋯O and O-H⋯Cl hydrogen bonds, forming layers stacked along [20].

Related literature

For the biological activity of thia­zole derivatives, see: Turan-Zitouni et al. (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C7H11N2O2S+·Cl−·H2O

M = 240.70

Monoclinic,

a = 10.637 (2) Å

b = 7.4463 (15) Å

c = 15.082 (3) Å

β = 110.22 (3)°

V = 1121.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.51 mm−1

T = 292 K

0.40 × 0.32 × 0.28 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.821, T max = 0.868

11232 measured reflections

2564 independent reflections

2097 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.122

S = 1.12

2564 reflections

133 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear ; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024532/rz2337sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024532/rz2337Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C7H11N2O2S+·Cl−·H2O	F(000) = 504
Mr = 240.70	Dx = 1.426 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2280 reflections
a = 10.637 (2) Å	θ = 2.3–27.4°
b = 7.4463 (15) Å	µ = 0.51 mm−1
c = 15.082 (3) Å	T = 292 K
β = 110.22 (3)°	Block, colourless
V = 1121.0 (4) Å3	0.40 × 0.32 × 0.28 mm
Z = 4

Rigaku SCXmini diffractometer	2564 independent reflections
Radiation source: fine-focus sealed tube	2097 reflections with I > 2σ(I)
graphite	Rint = 0.037
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
Tmin = 0.821, Tmax = 0.868	l = −19→19
11232 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0547P)2 + 0.5076P] where P = (Fo2 + 2Fc2)/3
2564 reflections	(Δ/σ)max = 0.012
133 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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 > σ(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.

	x	y	z	Uiso*/Ueq
C1	0.5427 (2)	0.4538 (3)	0.14877 (16)	0.0386 (5)
C2	0.3764 (2)	0.2578 (3)	0.06588 (16)	0.0388 (5)
C3	0.3260 (3)	0.0717 (3)	0.0413 (2)	0.0542 (7)
H3A	0.2446	0.0563	0.0545	0.081*
H3B	0.3920	−0.0121	0.0781	0.081*
H3C	0.3088	0.0508	−0.0247	0.081*
C4	0.3170 (2)	0.4157 (3)	0.03211 (17)	0.0411 (5)
C5	0.1833 (2)	0.4419 (3)	−0.03804 (17)	0.0455 (6)
C6	0.0280 (3)	0.6581 (4)	−0.1270 (2)	0.0616 (8)
H6A	−0.0419	0.6052	−0.1079	0.074*
H6B	0.0199	0.6116	−0.1888	0.074*
C7	0.0156 (3)	0.8556 (5)	−0.1302 (3)	0.0850 (11)
H7A	0.0248	0.9001	−0.0686	0.128*
H7B	−0.0706	0.8889	−0.1742	0.128*
H7C	0.0846	0.9063	−0.1501	0.128*
Cl1	0.33656 (7)	0.42792 (8)	0.29075 (5)	0.0540 (2)
N1	0.65955 (19)	0.5069 (3)	0.20741 (15)	0.0499 (5)
H1A	0.7182	0.4290	0.2380	0.060*
H1B	0.6775	0.6197	0.2153	0.060*
N2	0.5037 (2)	0.2825 (2)	0.13088 (14)	0.0391 (4)
O1	0.10510 (19)	0.3235 (3)	−0.07219 (16)	0.0720 (6)
O2	0.15910 (17)	0.6150 (2)	−0.05873 (13)	0.0544 (5)
O1W	0.1705 (2)	0.7502 (3)	0.17716 (18)	0.0799 (7)
H1C	0.2076	0.6373	0.1937	0.120*
H1D	0.0879	0.7443	0.1503	0.120*
S1	0.41995 (6)	0.59887 (7)	0.08238 (4)	0.04234 (19)
H2	0.547 (2)	0.198 (3)	0.1547 (16)	0.033 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0338 (11)	0.0311 (10)	0.0441 (12)	0.0043 (8)	0.0047 (9)	0.0015 (9)
C2	0.0357 (11)	0.0341 (11)	0.0414 (11)	−0.0007 (9)	0.0067 (9)	0.0003 (9)
C3	0.0496 (15)	0.0364 (12)	0.0625 (16)	−0.0065 (11)	0.0014 (12)	0.0003 (11)
C4	0.0343 (11)	0.0361 (11)	0.0463 (12)	0.0002 (9)	0.0056 (9)	0.0017 (10)
C5	0.0342 (12)	0.0447 (13)	0.0498 (13)	0.0033 (10)	0.0048 (10)	0.0023 (11)
C6	0.0406 (14)	0.0564 (16)	0.0654 (17)	0.0121 (12)	−0.0103 (12)	−0.0003 (13)
C7	0.0572 (19)	0.0549 (18)	0.110 (3)	0.0138 (15)	−0.0128 (18)	0.0051 (18)
Cl1	0.0531 (4)	0.0343 (3)	0.0627 (4)	−0.0034 (2)	0.0047 (3)	−0.0010 (3)
N1	0.0366 (10)	0.0341 (10)	0.0610 (13)	0.0021 (8)	−0.0061 (9)	0.0015 (9)
N2	0.0359 (10)	0.0284 (9)	0.0443 (10)	0.0058 (8)	0.0028 (8)	0.0030 (8)
O1	0.0430 (11)	0.0534 (12)	0.0924 (15)	−0.0044 (9)	−0.0112 (10)	0.0004 (11)
O2	0.0409 (9)	0.0456 (10)	0.0582 (10)	0.0083 (7)	−0.0064 (8)	0.0013 (8)
O1W	0.0451 (11)	0.0465 (11)	0.1127 (17)	−0.0019 (9)	−0.0180 (11)	−0.0051 (11)
S1	0.0357 (3)	0.0299 (3)	0.0515 (3)	0.0048 (2)	0.0024 (2)	0.0036 (2)

C1—N1	1.313 (3)	C6—O2	1.454 (3)
C1—N2	1.339 (3)	C6—C7	1.476 (4)
C1—S1	1.724 (2)	C6—H6A	0.9700
C2—C4	1.348 (3)	C6—H6B	0.9700
C2—N2	1.382 (3)	C7—H7A	0.9600
C2—C3	1.486 (3)	C7—H7B	0.9600
C3—H3A	0.9600	C7—H7C	0.9600
C3—H3B	0.9600	N1—H1A	0.8600
C3—H3C	0.9600	N1—H1B	0.8600
C4—C5	1.463 (3)	N2—H2	0.79 (3)
C4—S1	1.750 (2)	O1W—H1C	0.9259
C5—O1	1.199 (3)	O1W—H1D	0.8324
C5—O2	1.330 (3)
N1—C1—N2	125.3 (2)	C7—C6—H6A	110.3
N1—C1—S1	123.57 (17)	O2—C6—H6B	110.3
N2—C1—S1	111.12 (16)	C7—C6—H6B	110.3
C4—C2—N2	111.61 (19)	H6A—C6—H6B	108.5
C4—C2—C3	129.6 (2)	C6—C7—H7A	109.5
N2—C2—C3	118.8 (2)	C6—C7—H7B	109.5
C2—C3—H3A	109.5	H7A—C7—H7B	109.5
C2—C3—H3B	109.5	C6—C7—H7C	109.5
H3A—C3—H3B	109.5	H7A—C7—H7C	109.5
C2—C3—H3C	109.5	H7B—C7—H7C	109.5
H3A—C3—H3C	109.5	C1—N1—H1A	120.0
H3B—C3—H3C	109.5	C1—N1—H1B	120.0
C2—C4—C5	126.9 (2)	H1A—N1—H1B	120.0
C2—C4—S1	112.00 (17)	C1—N2—C2	115.39 (18)
C5—C4—S1	121.05 (17)	C1—N2—H2	125.1 (18)
O1—C5—O2	124.2 (2)	C2—N2—H2	119.5 (18)
O1—C5—C4	124.7 (2)	C5—O2—C6	116.1 (2)
O2—C5—C4	111.1 (2)	H1C—O1W—H1D	111.3
O2—C6—C7	107.3 (2)	C1—S1—C4	89.88 (11)
O2—C6—H6A	110.3

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1Wi	0.86	1.94	2.789 (3)	169
N1—H1B···Cl1ii	0.86	2.30	3.135 (2)	164
O1W—H1C···Cl1	0.93	2.25	3.118 (2)	156
O1W—H1D···O1iii	0.83	2.05	2.863 (3)	167
N2—H2···Cl1i	0.79 (3)	2.35 (3)	3.141 (2)	173 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1Wi	0.86	1.94	2.789 (3)	169
N1—H1B⋯Cl1ii	0.86	2.30	3.135 (2)	164
O1W—H1C⋯Cl1	0.93	2.25	3.118 (2)	156
O1W—H1D⋯O1iii	0.83	2.05	2.863 (3)	167
N2—H2⋯Cl1i	0.79 (3)	2.35 (3)	3.141 (2)	173 (2)

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