Sodium piperidine-1-carbodithio-ate dihydrate.

The asymmetric unit of the title compound, Na(+)·C(6)H(10)NS(2) (-)·2H(2)O, is composed of a sodium cation, a piperidine-dithio-carbamate anion which exhibits positional disorder, and two lattice water mol-ecules. The atoms of the piperidine ring are divided over two sites with occupancy factors of 0.554 (6) and 0.446 (6). In the crystal, the sodium cation (coordination number of 6) and the piperidine-dithio-carbamate anion are linked, forming an infinite two-dimensional network extending parallel to (001). O-H⋯S hydrogen bonds, involving the lattice water mol-ecules, also aid in stabilizing the crystal sructure.

Related literature

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

Experimental

Crystal data

Na+·C6H10NS2 −·2H2O

M = 219.29

Monoclinic,

a = 12.241 (5) Å

b = 5.909 (5) Å

c = 14.690 (5) Å

β = 95.519 (5)°

V = 1057.6 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.51 mm−1

T = 290 K

0.02 × 0.02 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer

7553 measured reflections

1863 independent reflections

1482 reflections with I > 2σ(I)

R int = 0.145

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.152

S = 1.02

1863 reflections

176 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.36 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; 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 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811022604/su2283sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022604/su2283Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811022604/su2283Isup3.cml

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

Na+·C6H10NS2−·2H2O	F(000) = 464
Mr = 219.29	Dx = 1.377 Mg m−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yab	Cell parameters from 24030 reflections
a = 12.241 (5) Å	θ = 2.9–26.7°
b = 5.909 (5) Å	µ = 0.51 mm−1
c = 14.690 (5) Å	T = 290 K
β = 95.519 (5)°	Prism, colourless
V = 1057.6 (11) Å3	0.02 × 0.02 × 0.02 mm
Z = 4

Nonius KappaCCD diffractometer	1482 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590	Rint = 0.145
graphite	θmax = 25.1°, θmin = 3.3°
Detector resolution: 9 pixels mm-1	h = −14→14
CCD rotation images, thick slices scans	k = −7→6
7553 measured reflections	l = −17→16
1863 independent 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0964P)2] where P = (Fo2 + 2Fc2)/3
1863 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.33 e Å−3
6 restraints	Δρmin = −0.36 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	Occ. (<1)
S1	0.74854 (5)	0.03097 (13)	0.39216 (4)	0.0481 (3)
S2	0.86593 (6)	0.24242 (13)	0.24400 (5)	0.0577 (3)
Na1	0.57813 (8)	−0.24210 (16)	0.48568 (8)	0.0509 (4)
O1	0.41274 (14)	−0.0826 (4)	0.41396 (13)	0.0542 (5)
H11O	0.403 (3)	−0.012 (5)	0.3644 (17)	0.081*
H12O	0.369 (2)	−0.194 (4)	0.418 (2)	0.081*
O2	0.55132 (14)	−0.5918 (4)	0.40928 (13)	0.0533 (5)
H21O	0.509 (2)	−0.604 (6)	0.3618 (16)	0.08*
H22O	0.604 (2)	−0.687 (5)	0.409 (2)	0.08*
C1	0.7694 (2)	0.0599 (5)	0.27824 (18)	0.0551 (7)
N1	0.6797 (6)	0.0084 (12)	0.2149 (4)	0.0541 (16)	0.446 (6)
C2	0.6746 (8)	0.0673 (16)	0.1177 (5)	0.081 (3)	0.446 (6)
H2A	0.73	0.1807	0.1092	0.097*	0.446 (6)
H2B	0.6034	0.1336	0.0991	0.097*	0.446 (6)
C3	0.6917 (19)	−0.128 (5)	0.0585 (18)	0.095 (8)	0.446 (6)
H3A	0.7657	−0.1862	0.0716	0.114*	0.446 (6)
H3B	0.6818	−0.0832	−0.0053	0.114*	0.446 (6)
C4	0.6069 (10)	−0.314 (3)	0.0773 (10)	0.079 (4)	0.446 (6)
H4A	0.5339	−0.2616	0.0555	0.095*	0.446 (6)
H4B	0.6218	−0.449	0.043	0.095*	0.446 (6)
C5	0.6089 (7)	−0.3753 (16)	0.1787 (6)	0.076 (2)	0.446 (6)
H5A	0.5505	−0.4818	0.1877	0.091*	0.446 (6)
H5B	0.6784	−0.4451	0.1998	0.091*	0.446 (6)
C6	0.5931 (7)	−0.1592 (18)	0.2320 (6)	0.067 (2)	0.446 (6)
H6A	0.5213	−0.0958	0.2135	0.08*	0.446 (6)
H6B	0.5969	−0.1932	0.2969	0.08*	0.446 (6)
N1'	0.7338 (4)	−0.1085 (10)	0.2187 (3)	0.0516 (13)	0.554 (6)
C2'	0.7582 (5)	−0.1213 (13)	0.1240 (4)	0.0677 (19)	0.554 (6)
H2'1	0.7906	−0.267	0.1125	0.081*	0.554 (6)
H2'2	0.8103	−0.0042	0.1119	0.081*	0.554 (6)
C3'	0.6545 (14)	−0.091 (5)	0.0626 (11)	0.095 (6)	0.554 (6)
H3'1	0.6717	−0.1086	−0.0002	0.115*	0.554 (6)
H3'2	0.6291	0.0629	0.0693	0.115*	0.554 (6)
C4'	0.5616 (9)	−0.249 (3)	0.0778 (10)	0.111 (5)	0.554 (6)
H4'1	0.5798	−0.4026	0.0616	0.133*	0.554 (6)
H4'2	0.4954	−0.2037	0.0407	0.133*	0.554 (6)
C5'	0.5447 (6)	−0.2350 (14)	0.1783 (6)	0.082 (2)	0.554 (6)
H5'1	0.5157	−0.0869	0.1912	0.098*	0.554 (6)
H5'2	0.4909	−0.3471	0.1922	0.098*	0.554 (6)
C6'	0.6494 (6)	−0.2736 (13)	0.2392 (4)	0.0629 (18)	0.554 (6)
H6'1	0.6349	−0.2592	0.3027	0.075*	0.554 (6)
H6'2	0.6759	−0.4258	0.2299	0.075*	0.554 (6)

	U11	U22	U33	U12	U13	U23
S1	0.0420 (4)	0.0551 (5)	0.0476 (4)	0.0008 (3)	0.0057 (3)	−0.0027 (3)
S2	0.0586 (5)	0.0585 (6)	0.0565 (5)	−0.0121 (3)	0.0090 (3)	0.0002 (3)
Na1	0.0465 (6)	0.0453 (8)	0.0609 (7)	0.0002 (4)	0.0053 (5)	−0.0005 (5)
O1	0.0534 (11)	0.0470 (13)	0.0608 (12)	−0.0039 (9)	−0.0015 (9)	0.0059 (10)
O2	0.0502 (10)	0.0497 (13)	0.0597 (12)	0.0060 (9)	0.0033 (8)	−0.0031 (10)
C1	0.0574 (15)	0.056 (2)	0.0512 (15)	−0.0111 (13)	0.0027 (12)	−0.0035 (14)
N1	0.062 (4)	0.052 (4)	0.047 (3)	−0.008 (3)	−0.001 (3)	0.000 (2)
C2	0.108 (6)	0.080 (7)	0.051 (4)	−0.026 (5)	−0.008 (4)	0.007 (4)
C3	0.104 (14)	0.107 (13)	0.079 (10)	−0.051 (11)	0.044 (10)	−0.030 (8)
C4	0.077 (8)	0.090 (9)	0.070 (6)	−0.033 (7)	0.003 (6)	−0.028 (7)
C5	0.070 (5)	0.070 (6)	0.088 (6)	−0.017 (5)	0.014 (4)	0.000 (5)
C6	0.053 (4)	0.086 (7)	0.061 (4)	−0.022 (5)	0.010 (4)	−0.010 (5)
N1'	0.052 (3)	0.056 (3)	0.047 (2)	−0.011 (2)	0.0082 (18)	−0.007 (2)
C2'	0.071 (4)	0.084 (5)	0.050 (3)	−0.020 (3)	0.016 (3)	−0.018 (3)
C3'	0.105 (12)	0.130 (13)	0.049 (6)	−0.041 (9)	−0.004 (7)	0.016 (7)
C4'	0.082 (8)	0.148 (14)	0.096 (7)	−0.042 (7)	−0.030 (6)	0.037 (7)
C5'	0.061 (4)	0.077 (6)	0.107 (6)	−0.020 (4)	0.007 (4)	−0.002 (4)
C6'	0.066 (4)	0.060 (5)	0.061 (4)	−0.027 (3)	0.000 (3)	−0.009 (3)

S1—C1	1.726 (3)	C3—H3A	0.97
S1—Na1i	2.9644 (15)	C3—H3B	0.97
S1—Na1	3.0649 (15)	C4—C5	1.530 (18)
S2—C1	1.710 (3)	C4—H4A	0.97
Na1—O2	2.360 (3)	C4—H4B	0.97
Na1—O1	2.385 (2)	C5—C6	1.521 (14)
Na1—O1ii	2.416 (3)	C5—H5A	0.97
Na1—O2iii	2.515 (2)	C5—H5B	0.97
Na1—S1iv	2.9644 (15)	C6—H6A	0.97
Na1—Na1ii	3.490 (3)	C6—H6B	0.97
Na1—Na1iii	3.644 (3)	N1'—C2'	1.452 (6)
Na1—H12O	2.67 (3)	N1'—C6'	1.473 (7)
O1—Na1ii	2.416 (3)	C2'—C3'	1.495 (19)
O1—H11O	0.839 (17)	C2'—H2'1	0.97
O1—H12O	0.852 (17)	C2'—H2'2	0.97
O2—Na1iii	2.515 (2)	C3'—C4'	1.50 (3)
O2—H21O	0.834 (17)	C3'—H3'1	0.97
O2—H22O	0.856 (17)	C3'—H3'2	0.97
C1—N1'	1.368 (5)	C4'—C5'	1.512 (17)
C1—N1	1.403 (6)	C4'—H4'1	0.97
N1—C2	1.465 (9)	C4'—H4'2	0.97
N1—C6	1.489 (10)	C5'—C6'	1.507 (11)
C2—C3	1.47 (3)	C5'—H5'1	0.97
C2—H2A	0.97	C5'—H5'2	0.97
C2—H2B	0.97	C6'—H6'1	0.97
C3—C4	1.55 (3)	C6'—H6'2	0.97
C1—S1—Na1i	112.20 (10)	C3—C2—H2A	108.9
C1—S1—Na1	131.13 (10)	N1—C2—H2B	108.9
Na1i—S1—Na1	116.43 (4)	C3—C2—H2B	108.9
O2—Na1—O1	93.59 (8)	H2A—C2—H2B	107.8
O2—Na1—O1ii	169.15 (8)	C2—C3—C4	108.3 (14)
O1—Na1—O1ii	86.75 (8)	C2—C3—H3A	110
O2—Na1—O2iii	83.29 (8)	C4—C3—H3A	110
O1—Na1—O2iii	82.36 (7)	C2—C3—H3B	110
O1ii—Na1—O2iii	86.01 (8)	C4—C3—H3B	110
O2—Na1—S1iv	87.16 (7)	H3A—C3—H3B	108.4
O1—Na1—S1iv	166.91 (6)	C5—C4—C3	113.1 (13)
O1ii—Na1—S1iv	90.09 (7)	C5—C4—H4A	109
O2iii—Na1—S1iv	84.76 (6)	C3—C4—H4A	109
O2—Na1—S1	108.51 (7)	C5—C4—H4B	109
O1—Na1—S1	100.34 (7)	C3—C4—H4B	109
O1ii—Na1—S1	82.06 (7)	H4A—C4—H4B	107.8
O2iii—Na1—S1	167.57 (6)	C6—C5—C4	108.2 (9)
S1iv—Na1—S1	91.78 (4)	C6—C5—H5A	110.1
O2—Na1—Na1ii	136.28 (8)	C4—C5—H5A	110.1
O1—Na1—Na1ii	43.73 (6)	C6—C5—H5B	110.1
O1ii—Na1—Na1ii	43.02 (5)	C4—C5—H5B	110.1
O2iii—Na1—Na1ii	82.00 (7)	H5A—C5—H5B	108.4
S1iv—Na1—Na1ii	131.81 (6)	N1—C6—C5	110.1 (6)
S1—Na1—Na1ii	91.55 (6)	N1—C6—H6A	109.6
O2—Na1—Na1iii	43.27 (6)	C5—C6—H6A	109.6
O1—Na1—Na1iii	87.06 (7)	N1—C6—H6B	109.6
O1ii—Na1—Na1iii	126.00 (8)	C5—C6—H6B	109.6
O2iii—Na1—Na1iii	40.02 (5)	H6A—C6—H6B	108.2
S1iv—Na1—Na1iii	84.54 (5)	C1—N1'—C2'	124.6 (4)
S1—Na1—Na1iii	151.58 (5)	C1—N1'—C6'	122.6 (4)
Na1ii—Na1—Na1iii	111.83 (7)	C2'—N1'—C6'	111.9 (5)
O2—Na1—H12O	80.3 (6)	N1'—C2'—C3'	109.4 (7)
O1—Na1—H12O	18.4 (4)	N1'—C2'—H2'1	109.8
O1ii—Na1—H12O	97.4 (7)	C3'—C2'—H2'1	109.8
O2iii—Na1—H12O	68.4 (5)	N1'—C2'—H2'2	109.8
S1iv—Na1—H12O	151.4 (5)	C3'—C2'—H2'2	109.8
S1—Na1—H12O	116.5 (5)	H2'1—C2'—H2'2	108.2
Na1ii—Na1—H12O	56.0 (6)	C2'—C3'—C4'	116.5 (14)
Na1iii—Na1—H12O	68.7 (4)	C2'—C3'—H3'1	108.2
Na1—O1—Na1ii	93.25 (8)	C4'—C3'—H3'1	108.2
Na1—O1—H11O	129 (2)	C2'—C3'—H3'2	108.2
Na1ii—O1—H11O	97 (3)	C4'—C3'—H3'2	108.2
Na1—O1—H12O	100 (2)	H3'1—C3'—H3'2	107.3
Na1ii—O1—H12O	124 (2)	C3'—C4'—C5'	106.7 (11)
H11O—O1—H12O	114 (3)	C3'—C4'—H4'1	110.4
Na1—O2—Na1iii	96.71 (8)	C5'—C4'—H4'1	110.4
Na1—O2—H21O	121 (3)	C3'—C4'—H4'2	110.4
Na1iii—O2—H21O	96 (2)	C5'—C4'—H4'2	110.4
Na1—O2—H22O	121 (2)	H4'1—C4'—H4'2	108.6
Na1iii—O2—H22O	106 (2)	C6'—C5'—C4'	112.5 (7)
H21O—O2—H22O	111 (2)	C6'—C5'—H5'1	109.1
N1'—C1—N1	40.3 (3)	C4'—C5'—H5'1	109.1
N1'—C1—S2	117.2 (3)	C6'—C5'—H5'2	109.1
N1—C1—S2	117.4 (3)	C4'—C5'—H5'2	109.1
N1'—C1—S1	118.6 (3)	H5'1—C5'—H5'2	107.8
N1—C1—S1	116.2 (3)	N1'—C6'—C5'	110.6 (5)
S2—C1—S1	121.25 (16)	N1'—C6'—H6'1	109.5
C1—N1—C2	123.5 (5)	C5'—C6'—H6'1	109.5
C1—N1—C6	123.9 (6)	N1'—C6'—H6'2	109.5
C2—N1—C6	111.0 (6)	C5'—C6'—H6'2	109.5
N1—C2—C3	113.2 (13)	H6'1—C6'—H6'2	108.1
N1—C2—H2A	108.9
C1—S1—Na1—O2	38.84 (16)	Na1i—S1—C1—S2	−10.8 (2)
Na1i—S1—Na1—O2	−135.11 (7)	Na1—S1—C1—S2	175.08 (10)
C1—S1—Na1—O1	−58.52 (16)	N1'—C1—N1—C2	−89.0 (9)
Na1i—S1—Na1—O1	127.53 (7)	S2—C1—N1—C2	11.7 (9)
C1—S1—Na1—O1ii	−143.72 (15)	S1—C1—N1—C2	166.8 (6)
Na1i—S1—Na1—O1ii	42.34 (6)	N1'—C1—N1—C6	75.0 (8)
C1—S1—Na1—O2iii	−160.0 (3)	S2—C1—N1—C6	175.6 (6)
Na1i—S1—Na1—O2iii	26.0 (3)	S1—C1—N1—C6	−29.3 (9)
C1—S1—Na1—S1iv	126.44 (14)	C1—N1—C2—C3	104.9 (12)
Na1i—S1—Na1—S1iv	−47.50 (6)	C6—N1—C2—C3	−60.8 (14)
C1—S1—Na1—Na1ii	−101.64 (15)	N1—C2—C3—C4	55 (2)
Na1i—S1—Na1—Na1ii	84.41 (5)	C2—C3—C4—C5	−53 (2)
C1—S1—Na1—Na1iii	44.63 (19)	C3—C4—C5—C6	54.8 (15)
Na1i—S1—Na1—Na1iii	−129.32 (11)	C1—N1—C6—C5	−105.1 (9)
O2—Na1—O1—Na1ii	169.13 (8)	C2—N1—C6—C5	60.6 (11)
O1ii—Na1—O1—Na1ii	0	C4—C5—C6—N1	−57.2 (11)
O2iii—Na1—O1—Na1ii	86.40 (8)	N1—C1—N1'—C2'	90.7 (8)
S1iv—Na1—O1—Na1ii	76.2 (3)	S2—C1—N1'—C2'	−10.6 (7)
S1—Na1—O1—Na1ii	−81.31 (7)	S1—C1—N1'—C2'	−171.6 (4)
Na1iii—Na1—O1—Na1ii	126.33 (8)	N1—C1—N1'—C6'	−77.5 (6)
O1—Na1—O2—Na1iii	−81.86 (8)	S2—C1—N1'—C6'	−178.7 (4)
O1ii—Na1—O2—Na1iii	9.6 (5)	S1—C1—N1'—C6'	20.2 (7)
O2iii—Na1—O2—Na1iii	0	C1—N1'—C2'—C3'	−113.5 (12)
S1iv—Na1—O2—Na1iii	85.05 (6)	C6'—N1'—C2'—C3'	55.7 (13)
S1—Na1—O2—Na1iii	175.98 (6)	N1'—C2'—C3'—C4'	−55 (2)
Na1ii—Na1—O2—Na1iii	−70.99 (11)	C2'—C3'—C4'—C5'	52.4 (19)
Na1i—S1—C1—N1'	149.5 (3)	C3'—C4'—C5'—C6'	−52.4 (15)
Na1—S1—C1—N1'	−24.6 (4)	C1—N1'—C6'—C5'	110.7 (7)
Na1i—S1—C1—N1	−164.9 (4)	C2'—N1'—C6'—C5'	−58.7 (9)
Na1—S1—C1—N1	21.0 (5)	C4'—C5'—C6'—N1'	57.7 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H11O···S2v	0.84 (2)	2.39 (2)	3.214 (2)	167 (3)
O1—H12O···S1vi	0.85 (2)	2.49 (2)	3.322 (3)	167 (3)
O2—H21O···S2vi	0.83 (2)	2.48 (2)	3.283 (2)	163 (3)
O2—H22O···S1vii	0.86 (2)	2.46 (2)	3.313 (2)	174 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H11O⋯S2i	0.84 (2)	2.39 (2)	3.214 (2)	167 (3)
O1—H12O⋯S1ii	0.85 (2)	2.49 (2)	3.322 (3)	167 (3)
O2—H21O⋯S2ii	0.83 (2)	2.48 (2)	3.283 (2)	163 (3)
O2—H22O⋯S1iii	0.86 (2)	2.46 (2)	3.313 (2)	174 (3)

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