3-Hydr­oxy-2-methyl­isothia­zolium chloride monohydrate: an inter­molecular three-dimensional network via O—H...O and O—H...Cl hydrogen bonds

The title compound, C₄H₆ClNOS·H₂O, has a planar five-membered ring, with a delocalized positive charge. A three-dimensional network is formed through inter­molecular O—H...O and O—H...Cl hydrogen bonds between 3-hydr­oxy-2-methyl­isothia­zolium cations and water mol­ecules, and between water mol­ecules and chloride anions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.098
• Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  Cl1    ..  S1      ..       3.11 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 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

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Computing details

Data collection: SMART-W2K/NT (Bruker, 2003); cell refinement: SAINT-W2K/NT (Bruker, 2003); data reduction: SAINT-W2K/NT; program(s) used to solve structure: SHELXTL-NT (Bruker, 2003); program(s) used to refine structure: SHELXTL-NT; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL-NT.

3-Hydroxy-2-methylisothiazolium chloride monohydrate

Crystal data

C4H6NOS^+·Cl^−·H2O	F(000) = 352
Mr = 169.62	Dx = 1.541 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1395 reflections
a = 6.0291 (6) Å	θ = 2.8–26.3°
b = 8.2420 (8) Å	µ = 0.74 mm^−1
c = 14.7222 (14) Å	T = 173 K
β = 91.921 (2)°	Block, colorless
V = 731.16 (12) Å^3	0.24 × 0.21 × 0.18 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	1743 independent reflections
Radiation source: fine-focus sealed tube	1477 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 8.366 pixels mm^-1	θmax = 27.9°, θmin = 2.8°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→7
Tmin = 0.843, Tmax = 0.879	l = −19→19
5225 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0514P)^2 + 0.0524P] where P = (Fo^2 + 2Fc^2)/3
1743 reflections	(Δ/σ)max < 0.001
95 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

3.1318 (0.0043) x + 6.3397 (0.0050) y - 5.7326 (0.0107) z = 1.9214 (0.0074)

* 0.0040 (0.0009) S1 * -0.0078 (0.0010) N1 * 0.0085 (0.0012) C1 * -0.0046 (0.0013) C2 * -0.0001 (0.0012) C3 0.0200 (0.0028) O1 0.0912 (0.0033) C4

Rms deviation of fitted atoms = 0.0058

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.36295 (9)	0.96320 (6)	0.33374 (3)	0.02883 (17)
S1	−0.22387 (9)	0.74074 (6)	0.36102 (3)	0.02494 (17)
O1	0.2917 (2)	0.60650 (18)	0.49143 (11)	0.0290 (4)
N1	0.0167 (3)	0.6416 (2)	0.38481 (11)	0.0218 (4)
C1	0.1044 (3)	0.6750 (2)	0.46684 (13)	0.0219 (4)
C4	0.1257 (4)	0.5417 (3)	0.31670 (15)	0.0295 (5)
H4A	0.2528	0.6009	0.2934	0.044*
H4B	0.0199	0.5177	0.2665	0.044*
H4C	0.1770	0.4401	0.3448	0.044*
C3	−0.2110 (4)	0.8279 (3)	0.46519 (14)	0.0270 (5)
H3	−0.3202	0.9009	0.4860	0.032*
C2	−0.0300 (4)	0.7835 (2)	0.51574 (15)	0.0260 (5)
H2	0.0029	0.8200	0.5759	0.031*
O2	0.4002 (4)	0.7069 (2)	0.64756 (12)	0.0421 (5)
H2B	0.396 (5)	0.655 (4)	0.693 (2)	0.058 (10)*
H1	0.331 (5)	0.636 (4)	0.544 (2)	0.060 (10)*
H2A	0.467 (6)	0.783 (4)	0.656 (2)	0.068 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0311 (3)	0.0292 (3)	0.0262 (3)	0.0001 (2)	0.0008 (2)	−0.0015 (2)
S1	0.0232 (3)	0.0287 (3)	0.0229 (3)	0.0009 (2)	0.0002 (2)	0.00017 (19)
O1	0.0274 (8)	0.0321 (9)	0.0271 (9)	0.0014 (7)	−0.0048 (7)	−0.0002 (6)
N1	0.0220 (8)	0.0236 (9)	0.0199 (9)	0.0004 (7)	0.0024 (7)	0.0002 (6)
C1	0.0232 (10)	0.0212 (10)	0.0213 (10)	−0.0050 (8)	0.0002 (8)	0.0035 (8)
C4	0.0296 (11)	0.0332 (12)	0.0261 (11)	0.0033 (9)	0.0049 (9)	−0.0061 (9)
C3	0.0300 (11)	0.0254 (11)	0.0257 (11)	0.0000 (9)	0.0044 (8)	−0.0025 (8)
C2	0.0306 (11)	0.0245 (11)	0.0231 (11)	−0.0033 (9)	0.0013 (8)	−0.0016 (8)
O2	0.0634 (13)	0.0362 (11)	0.0260 (10)	−0.0142 (9)	−0.0103 (8)	0.0035 (8)

Geometric parameters (Å, º)

S1—N1	1.6911 (17)	C4—H4B	0.9800
S1—C3	1.693 (2)	C4—H4C	0.9800
O1—C1	1.303 (2)	C3—C2	1.351 (3)
O1—H1	0.84 (3)	C3—H3	0.9500
N1—C1	1.331 (2)	C2—H2	0.9500
N1—C4	1.469 (3)	O2—H2B	0.79 (3)
C1—C2	1.419 (3)	O2—H2A	0.75 (3)
C4—H4A	0.9800
N1—S1—C3	90.26 (9)	N1—C4—H4C	109.5
C1—O1—H1	110 (2)	H4A—C4—H4C	109.5
C1—N1—C4	124.18 (17)	H4B—C4—H4C	109.5
C1—N1—S1	113.58 (14)	C2—C3—S1	113.30 (17)
C4—N1—S1	121.97 (14)	C2—C3—H3	123.3
O1—C1—N1	118.49 (18)	S1—C3—H3	123.3
O1—C1—C2	129.52 (19)	C3—C2—C1	110.85 (19)
N1—C1—C2	111.99 (18)	C3—C2—H2	124.6
N1—C4—H4A	109.5	C1—C2—H2	124.6
N1—C4—H4B	109.5	H2B—O2—H2A	110 (4)
H4A—C4—H4B	109.5
C3—S1—N1—C1	−1.08 (16)	S1—N1—C1—C2	1.6 (2)
C3—S1—N1—C4	−175.33 (17)	N1—S1—C3—C2	0.26 (17)
C4—N1—C1—O1	−5.0 (3)	S1—C3—C2—C1	0.6 (2)
S1—N1—C1—O1	−179.06 (14)	O1—C1—C2—C3	179.4 (2)
C4—N1—C1—C2	175.70 (17)	N1—C1—C2—C3	−1.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···Cl1^i	0.75 (3)	2.33 (3)	3.080 (2)	171 (4)
O2—H2B···Cl1^ii	0.79 (3)	2.31 (3)	3.093 (2)	172 (3)
O1—H1···O2	0.84 (3)	1.67 (3)	2.509 (2)	176 (3)

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