Potassium morpholine-4-carbodithio-ate monohydrate.

In the ionic title compound, K(+)·C(5)H(8)NOS(2) (-)·H(2)O, the morpholine ring of the morpholine-4-carbodithio-ate anion has a chair conformation. The potassium cation is coordinated by four S and four O atoms in a bipyramidal reversed geometry. In the crystal, the three components are linked, generating infinite two-dimensional networks that lie parallel to the bc plane. These layers are linked via O-H⋯S hydrogen bonds, forming a three-dimensional structure.

Related literature

For the crystal structures of similar compounds, see: Oskarsson et al. (1979 ▶); Albertsson et al. (1980 ▶); Ymén (1982 ▶); Mafud & Gambardella (2011a ▶,b ▶); Mafud et al. (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

K+·C5H8NOS2 −·H2O

M = 219.36

Monoclinic,

a = 6.7235 (10) Å

b = 17.260 (4) Å

c = 8.1904 (10) Å

β = 108.994 (10)°

V = 898.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.01 mm−1

T = 290 K

0.45 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer

Absorption correction: refined from ΔF (Walker & Stuart, 1983 ▶) T min = 0.512, T max = 0.818

2779 measured reflections

2618 independent reflections

1615 reflections with I > 2σ(I)

R int = 0.027

3 standard reflections every 120 min intensity decay: 10%

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.130

S = 1.01

2618 reflections

106 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.61 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812029613/su2446sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029613/su2446Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029613/su2446Isup3.cml

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

K+·C5H8NOS2−·H2O	F(000) = 456
Mr = 219.36	Dx = 1.621 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16 reflections
a = 6.7235 (10) Å	θ = 9.8–18.3°
b = 17.260 (4) Å	µ = 1.01 mm−1
c = 8.1904 (10) Å	T = 290 K
β = 108.994 (10)°	Prism, colourless
V = 898.7 (3) Å3	0.45 × 0.3 × 0.2 mm
Z = 4

Enraf–Nonius TurboCAD-4 diffractometer	1615 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590	Rint = 0.027
Graphite monochromator	θmax = 30.0°, θmin = 2.4°
non–profiled ω/2θ scans	h = −9→8
Absorption correction: part of the refinement model (ΔF) (Walker & Stuart, 1983)	k = 0→24
Tmin = 0.512, Tmax = 0.818	l = 0→11
2779 measured reflections	3 standard reflections every 120 min
2618 independent reflections	intensity decay: 10%

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0644P)2] where P = (Fo2 + 2Fc2)/3
2618 reflections	(Δ/σ)max < 0.001
106 parameters	Δρmax = 0.50 e Å−3
3 restraints	Δρmin = −0.61 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
K1	−0.28085 (12)	0.24637 (4)	0.48217 (9)	0.0366 (2)
S1	−0.06278 (13)	−0.16683 (4)	0.69255 (11)	0.0320 (2)
S2	0.36659 (13)	−0.09853 (4)	0.80129 (12)	0.0336 (3)
O1	−0.1501 (4)	0.13219 (12)	0.7743 (3)	0.0366 (7)
O2	−0.5955 (4)	0.27515 (16)	0.1617 (4)	0.0496 (9)
N1	0.0172 (4)	−0.01514 (13)	0.7295 (3)	0.0261 (7)
C1	0.1003 (5)	−0.08662 (15)	0.7399 (4)	0.0240 (8)
C2	0.1460 (5)	0.05521 (16)	0.7583 (4)	0.0293 (9)
C3	0.0660 (5)	0.11438 (18)	0.8574 (4)	0.0334 (10)
C4	−0.2719 (5)	0.06303 (18)	0.7624 (5)	0.0348 (10)
C5	−0.2096 (4)	0.00131 (17)	0.6581 (4)	0.0289 (8)
H1O	−0.682 (6)	0.3070 (18)	0.093 (5)	0.0740*
H2A	0.14220	0.07690	0.64810	0.0350*
H2B	0.29080	0.04230	0.82250	0.0350*
H2O	−0.645 (7)	0.2294 (12)	0.154 (6)	0.0740*
H3A	0.08450	0.09460	0.97230	0.0400*
H3B	0.14850	0.16140	0.86940	0.0400*
H4A	−0.41980	0.07520	0.70910	0.0420*
H4B	−0.25230	0.04350	0.87770	0.0420*
H5A	−0.28850	−0.04570	0.65890	0.0350*
H5B	−0.24380	0.01850	0.53940	0.0350*

	U11	U22	U33	U12	U13	U23
K1	0.0408 (4)	0.0356 (4)	0.0341 (4)	−0.0006 (3)	0.0130 (3)	−0.0026 (3)
S1	0.0383 (4)	0.0207 (3)	0.0366 (4)	−0.0060 (3)	0.0116 (3)	−0.0032 (3)
S2	0.0297 (4)	0.0270 (4)	0.0454 (5)	0.0033 (3)	0.0141 (3)	−0.0004 (3)
O1	0.0370 (12)	0.0220 (10)	0.0551 (15)	0.0040 (9)	0.0210 (11)	−0.0031 (10)
O2	0.0444 (15)	0.0393 (14)	0.0546 (17)	0.0006 (12)	0.0018 (13)	0.0048 (13)
N1	0.0270 (12)	0.0204 (11)	0.0339 (14)	−0.0009 (9)	0.0142 (10)	−0.0035 (10)
C1	0.0313 (14)	0.0203 (13)	0.0231 (14)	−0.0011 (11)	0.0124 (11)	−0.0031 (11)
C2	0.0310 (15)	0.0205 (13)	0.0400 (18)	−0.0044 (11)	0.0164 (14)	−0.0021 (12)
C3	0.0356 (17)	0.0278 (15)	0.0381 (18)	−0.0040 (12)	0.0140 (14)	−0.0072 (13)
C4	0.0326 (16)	0.0267 (15)	0.051 (2)	0.0004 (12)	0.0218 (15)	−0.0025 (14)
C5	0.0267 (14)	0.0255 (14)	0.0349 (16)	−0.0005 (11)	0.0108 (13)	−0.0004 (12)

K1—O1	3.002 (2)	N1—C2	1.465 (4)
K1—O2	2.828 (3)	N1—C1	1.346 (4)
K1—S1i	3.2670 (13)	N1—C5	1.472 (4)
K1—S2i	3.3630 (13)	C2—C3	1.508 (4)
K1—S1ii	3.3797 (14)	C4—C5	1.508 (5)
K1—S2ii	3.3708 (13)	C2—H2A	0.9700
K1—O1iii	3.007 (3)	C2—H2B	0.9700
K1—O2iv	2.967 (3)	C3—H3A	0.9700
S1—C1	1.730 (3)	C3—H3B	0.9700
S2—C1	1.707 (4)	C4—H4A	0.9700
O1—C3	1.423 (4)	C4—H4B	0.9700
O1—C4	1.433 (4)	C5—H5A	0.9700
O2—H2O	0.85 (3)	C5—H5B	0.9700
O2—H1O	0.86 (4)
O1—K1—O2	142.34 (8)	K1iv—O1—C3	108.72 (17)
S1i—K1—O1	72.85 (5)	K1iv—O1—C4	110.7 (2)
S2i—K1—O1	99.11 (5)	K1—O2—K1iii	89.96 (8)
S1ii—K1—O1	90.44 (6)	K1iii—O2—H2O	100 (3)
S2ii—K1—O1	89.55 (5)	K1—O2—H2O	94 (3)
O1—K1—O1iii	147.70 (8)	H1O—O2—H2O	112 (4)
O1—K1—O2iv	66.04 (8)	K1—O2—H1O	149 (2)
S1i—K1—O2	142.49 (6)	K1iii—O2—H1O	101 (3)
S2i—K1—O2	98.33 (6)	C1—N1—C5	123.9 (3)
S1ii—K1—O2	94.95 (6)	C2—N1—C5	112.7 (2)
S2ii—K1—O2	65.49 (6)	C1—N1—C2	122.6 (3)
O1iii—K1—O2	67.68 (8)	S1—C1—N1	120.0 (3)
O2—K1—O2iv	92.48 (9)	S2—C1—N1	120.2 (2)
S1i—K1—S2i	53.28 (3)	S1—C1—S2	119.81 (16)
S1i—K1—S1ii	97.59 (3)	N1—C2—C3	110.6 (3)
S1i—K1—S2ii	145.67 (4)	O1—C3—C2	112.1 (3)
S1i—K1—O1iii	83.26 (5)	O1—C4—C5	111.7 (3)
S1i—K1—O2iv	94.72 (6)	N1—C5—C4	110.7 (3)
S1ii—K1—S2i	143.59 (3)	N1—C2—H2A	110.00
S2i—K1—S2ii	161.01 (4)	N1—C2—H2B	109.00
S2i—K1—O1iii	82.85 (5)	C3—C2—H2A	109.00
S2i—K1—O2iv	64.28 (6)	C3—C2—H2B	110.00
S1ii—K1—S2ii	52.27 (3)	H2A—C2—H2B	108.00
S1ii—K1—O1iii	71.17 (5)	O1—C3—H3A	109.00
S1ii—K1—O2iv	148.77 (6)	O1—C3—H3B	109.00
S2ii—K1—O1iii	98.84 (5)	C2—C3—H3A	109.00
S2ii—K1—O2iv	104.89 (6)	C2—C3—H3B	109.00
O1iii—K1—O2iv	139.03 (8)	H3A—C3—H3B	108.00
K1v—S1—C1	87.47 (11)	O1—C4—H4A	109.00
K1ii—S1—C1	87.09 (11)	O1—C4—H4B	109.00
K1v—S1—K1ii	76.09 (3)	C5—C4—H4A	109.00
K1v—S2—C1	84.71 (10)	C5—C4—H4B	109.00
K1ii—S2—C1	87.73 (10)	H4A—C4—H4B	108.00
K1v—S2—K1ii	74.95 (2)	N1—C5—H5A	110.00
K1—O1—C3	120.77 (19)	N1—C5—H5B	110.00
K1—O1—C4	118.7 (2)	C4—C5—H5A	109.00
K1—O1—K1iv	85.98 (6)	C4—C5—H5B	109.00
C3—O1—C4	108.9 (2)	H5A—C5—H5B	108.00
O2—K1—O1—C3	142.4 (2)	O2—K1—S1ii—C1ii	−72.98 (12)
O2—K1—O1—C4	3.2 (3)	O2—K1—S1ii—K1iii	15.13 (6)
O2—K1—O1—K1iv	−108.20 (12)	O1—K1—S2ii—C1ii	−71.26 (12)
S1i—K1—O1—C3	−54.13 (19)	O1—K1—S2ii—K1iii	−156.39 (6)
S1i—K1—O1—C4	166.7 (2)	O2—K1—S2ii—C1ii	137.86 (12)
S1i—K1—O1—K1iv	55.30 (5)	O2—K1—S2ii—K1iii	52.73 (7)
S2i—K1—O1—C3	−101.0 (2)	O1—K1—O1iii—K1iii	111.73 (12)
S2i—K1—O1—C4	119.8 (2)	O1—K1—O1iii—C3iii	−9.5 (2)
S2i—K1—O1—K1iv	8.40 (6)	O1—K1—O1iii—C4iii	−129.1 (2)
S1ii—K1—O1—C3	43.7 (2)	O2—K1—O1iii—K1iii	−50.45 (8)
S1ii—K1—O1—C4	−95.5 (2)	O2—K1—O1iii—C3iii	−171.6 (2)
S1ii—K1—O1—K1iv	153.11 (5)	O2—K1—O1iii—C4iii	68.8 (2)
S2ii—K1—O1—C3	96.0 (2)	O1—K1—O2iv—K1iv	52.11 (7)
S2ii—K1—O1—C4	−43.2 (2)	O2—K1—O2iv—K1iv	−159.92 (8)
S2ii—K1—O1—K1iv	−154.62 (6)	K1v—S1—C1—S2	39.50 (18)
O1iii—K1—O1—C3	−10.0 (3)	K1v—S1—C1—N1	−140.0 (2)
O1iii—K1—O1—C4	−149.2 (2)	K1ii—S1—C1—S2	−36.69 (18)
O1iii—K1—O1—K1iv	99.41 (13)	K1ii—S1—C1—N1	143.8 (2)
O2iv—K1—O1—C3	−157.5 (2)	K1v—S2—C1—S1	−38.31 (18)
O2iv—K1—O1—C4	63.4 (2)	K1v—S2—C1—N1	141.2 (3)
O2iv—K1—O1—K1iv	−48.08 (8)	K1ii—S2—C1—S1	36.78 (18)
O1—K1—O2—K1iii	−113.36 (12)	K1ii—S2—C1—N1	−143.7 (2)
S1i—K1—O2—K1iii	93.11 (11)	K1—O1—C3—C2	−81.8 (3)
S2i—K1—O2—K1iii	129.81 (6)	C4—O1—C3—C2	60.9 (3)
S1ii—K1—O2—K1iii	−16.20 (6)	K1iv—O1—C3—C2	−178.43 (19)
S2ii—K1—O2—K1iii	−60.59 (5)	K1—O1—C4—C5	82.8 (3)
O1iii—K1—O2—K1iii	51.11 (7)	C3—O1—C4—C5	−60.7 (3)
O2iv—K1—O2—K1iii	−165.83 (8)	K1iv—O1—C4—C5	179.8 (2)
O1—K1—S1i—C1i	−136.36 (13)	C2—N1—C1—S1	−176.4 (2)
O1—K1—S1i—K1iv	−48.73 (6)	C2—N1—C1—S2	4.1 (4)
O2—K1—S1i—C1i	27.08 (16)	C5—N1—C1—S1	−8.1 (4)
O2—K1—S1i—K1iv	114.71 (11)	C5—N1—C1—S2	172.4 (2)
O1—K1—S2i—C1i	81.34 (12)	C1—N1—C2—C3	−140.7 (3)
O1—K1—S2i—K1iv	−7.73 (6)	C5—N1—C2—C3	49.8 (3)
O2—K1—S2i—C1i	−132.18 (12)	C1—N1—C5—C4	140.7 (3)
O2—K1—S2i—K1iv	138.75 (7)	C2—N1—C5—C4	−50.0 (3)
O1—K1—S1ii—C1ii	69.70 (12)	N1—C2—C3—O1	−55.7 (3)
O1—K1—S1ii—K1iii	157.81 (5)	O1—C4—C5—N1	55.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O···S1vi	0.86 (4)	2.45 (4)	3.219 (3)	149 (3)
O2—H2O···S1vii	0.85 (3)	2.87 (5)	3.462 (3)	129 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O⋯S1i	0.86 (4)	2.45 (4)	3.219 (3)	149 (3)
O2—H2O⋯S1ii	0.85 (3)	2.87 (5)	3.462 (3)	129 (4)

Symmetry codes: (i) ; (ii) .