Ammonium piperidine-1-carbodithio-ate.

The title compound, NH(4) (+)·C(6)H(10)NS(2) (-), is composed of an ammonium cation and a piperidine-1-carbodithio-ate anion which exhibits positional disorder. The atoms of the ring have a structural disorder and they are divided into two sites, with occupancy factors of 0.584 and 0.426.. In the crystal, the cation and anion are linked by N-H⋯S hydrogen bonds to form an infinite two-dimensional network.

Related literature

For the crystal structures of similar compounds, see: Wahlberg (1979 ▶, 1980 ▶, 1981 ▶).

Experimental

Crystal data

NH4 +·C6H10NS2 −

M = 178.31

Monoclinic,

a = 8.8812 (9) Å

b = 9.0025 (9) Å

c = 11.8995 (5) Å

β = 104.318 (5)°

V = 921.85 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.51 mm−1

T = 290 K

0.40 × 0.35 × 0.13 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.582, T max = 0.936

2847 measured reflections

2684 independent reflections

2093 reflections with I > 2σ(I)

R int = 0.015

3 standard reflections every 120 min intensity decay: 5%

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.123

S = 1.06

2684 reflections

153 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.57 e Å−3

Δρmin = −0.29 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: SHELXS97 (Sheldrick, 2008 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536811008129/su2257sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008129/su2257Isup2.hkl

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

NH4+·C6H10NS2−	F(000) = 384
Mr = 178.31	Dx = 1.285 Mg m−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yab	Cell parameters from 14 reflections
a = 8.8812 (9) Å	θ = 12.0–18.1°
b = 9.0025 (9) Å	µ = 0.51 mm−1
c = 11.8995 (5) Å	T = 290 K
β = 104.318 (5)°	Prism, colourless
V = 921.85 (14) Å3	0.40 × 0.35 × 0.13 mm
Z = 4

Enraf–Nonius TurboCAD-4 diffractometer	2093 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
graphite	θmax = 30.0°, θmin = 2.9°
non–profiled ω/2θ scans	h = 0→12
Absorption correction: ψ scan (North et al., 1968)	k = −12→0
Tmin = 0.582, Tmax = 0.936	l = −16→16
2847 measured reflections	3 standard reflections every 120 min
2684 independent reflections	intensity decay: 5%

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.042	w = 1/[σ2(Fo2) + (0.075P)2 + 0.1152P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.123	(Δ/σ)max = 0.022
S = 1.06	Δρmax = 0.57 e Å−3
2684 reflections	Δρmin = −0.29 e Å−3
153 parameters

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.77666 (5)	0.04141 (4)	0.55813 (3)	0.0404 (1)
S2	0.83657 (6)	−0.11212 (5)	0.78409 (4)	0.0531 (1)
N2	0.8144 (3)	0.17995 (18)	0.76181 (14)	0.0669 (6)
C1	0.80997 (19)	0.05002 (17)	0.70767 (14)	0.0391 (4)
C2A	0.7452 (6)	0.3162 (4)	0.6942 (3)	0.0549 (13)	0.584 (8)
C3A	0.8316 (9)	0.4502 (5)	0.7551 (5)	0.0625 (15)	0.584 (8)
C4A	0.7868 (18)	0.4519 (18)	0.8807 (15)	0.077 (4)	0.584 (8)
C5A	0.8614 (7)	0.3215 (5)	0.9445 (4)	0.0629 (15)	0.584 (8)
C6A	0.7972 (9)	0.1813 (7)	0.8853 (5)	0.0666 (18)	0.584 (8)
C6B	0.8811 (14)	0.1978 (9)	0.8936 (6)	0.073 (3)	0.416 (8)
C3B	0.7530 (10)	0.4409 (9)	0.7391 (7)	0.062 (2)	0.416 (8)
C4B	0.816 (3)	0.472 (3)	0.866 (2)	0.079 (5)	0.416 (8)
C2B	0.8552 (8)	0.3244 (5)	0.7066 (4)	0.0507 (16)	0.416 (8)
C5B	0.7715 (14)	0.3116 (13)	0.9232 (7)	0.096 (4)	0.416 (8)
N1	0.47677 (19)	0.24531 (19)	0.40932 (17)	0.0468 (5)
H2A2	0.75640	0.31040	0.61520	0.0660*	0.584 (8)
H3A1	0.79720	0.54060	0.71210	0.0750*	0.584 (8)
H2A1	0.63550	0.32370	0.69170	0.0660*	0.584 (8)
H6A1	0.68830	0.17260	0.88500	0.0800*	0.584 (8)
H6A2	0.85200	0.09700	0.92730	0.0800*	0.584 (8)
H3A2	0.94280	0.43950	0.76510	0.0750*	0.584 (8)
H4A1	0.82450	0.54210	0.92290	0.0920*	0.584 (8)
H4A2	0.67500	0.44680	0.86980	0.0920*	0.584 (8)
H5A1	0.84560	0.32270	1.02230	0.0750*	0.584 (8)
H5A2	0.97240	0.32560	0.95090	0.0750*	0.584 (8)
H2B1	0.96390	0.34930	0.73690	0.0610*	0.416 (8)
H2B2	0.83420	0.31450	0.62300	0.0610*	0.416 (8)
H3B1	0.75430	0.53050	0.69410	0.0740*	0.416 (8)
H3B2	0.64680	0.40540	0.72460	0.0740*	0.416 (8)
H4B1	0.76550	0.55630	0.89120	0.0950*	0.416 (8)
H4B2	0.92780	0.48860	0.88470	0.0950*	0.416 (8)
H5B1	0.78720	0.32050	1.00650	0.1150*	0.416 (8)
H5B2	0.66410	0.28440	0.88930	0.1150*	0.416 (8)
H6B1	0.87760	0.10500	0.93420	0.0870*	0.416 (8)
H6B2	0.98710	0.23420	0.91150	0.0870*	0.416 (8)
H1	0.522 (3)	0.290 (3)	0.372 (2)	0.068 (8)*
H2	0.542 (3)	0.184 (3)	0.4556 (19)	0.055 (6)*
H3	0.448 (3)	0.308 (3)	0.463 (2)	0.081 (8)*
H4	0.393 (4)	0.201 (3)	0.365 (3)	0.090 (9)*

	U11	U22	U33	U12	U13	U23
S1	0.0487 (2)	0.0370 (2)	0.0367 (2)	0.0034 (2)	0.0126 (2)	0.0006 (1)
S2	0.0722 (3)	0.0415 (2)	0.0449 (2)	−0.0032 (2)	0.0132 (2)	0.0091 (2)
N2	0.1274 (16)	0.0387 (8)	0.0397 (7)	0.0076 (9)	0.0302 (9)	−0.0007 (6)
C1	0.0447 (8)	0.0371 (7)	0.0379 (7)	−0.0001 (6)	0.0150 (6)	0.0017 (6)
C2A	0.071 (3)	0.0412 (16)	0.0505 (17)	0.0079 (16)	0.0113 (16)	−0.0034 (12)
C3A	0.077 (3)	0.0394 (17)	0.068 (3)	−0.001 (2)	0.012 (3)	−0.0056 (16)
C4A	0.105 (6)	0.067 (8)	0.063 (5)	0.019 (6)	0.030 (4)	−0.021 (4)
C5A	0.071 (3)	0.072 (3)	0.0455 (18)	0.000 (2)	0.014 (2)	−0.0168 (17)
C6A	0.101 (4)	0.066 (3)	0.0404 (19)	−0.004 (3)	0.032 (3)	−0.0098 (17)
C6B	0.122 (7)	0.059 (3)	0.039 (3)	−0.011 (5)	0.024 (4)	0.000 (2)
C3B	0.058 (4)	0.059 (3)	0.067 (4)	0.016 (3)	0.014 (3)	−0.011 (3)
C4B	0.130 (11)	0.050 (4)	0.067 (7)	−0.008 (6)	0.043 (6)	−0.017 (4)
C2B	0.070 (4)	0.0338 (19)	0.052 (2)	0.007 (2)	0.022 (2)	0.0016 (16)
C5B	0.097 (6)	0.144 (9)	0.058 (4)	−0.023 (6)	0.040 (4)	−0.038 (5)
N1	0.0396 (8)	0.0394 (7)	0.0623 (9)	−0.0031 (6)	0.0141 (7)	0.0027 (7)

S1—C1	1.7319 (17)	C2A—H2A2	0.9700
S2—C1	1.7050 (16)	C2B—H2B1	0.9700
N2—C1	1.331 (2)	C2B—H2B2	0.9700
N2—C2A	1.512 (4)	C3A—H3A1	0.9700
N2—C6A	1.515 (6)	C3A—H3A2	0.9700
N2—C2B	1.540 (5)	C3B—H3B1	0.9700
N2—C6B	1.542 (7)	C3B—H3B2	0.9700
N1—H4	0.89 (3)	C4A—H4A1	0.9700
N1—H3	0.93 (3)	C4A—H4A2	0.9700
N1—H1	0.78 (3)	C4B—H4B2	0.9700
N1—H2	0.89 (3)	C4B—H4B1	0.9700
C2A—C3A	1.515 (7)	C5A—H5A1	0.9700
C2B—C3B	1.499 (10)	C5A—H5A2	0.9700
C3A—C4A	1.639 (18)	C5B—H5B1	0.9700
C3B—C4B	1.50 (2)	C5B—H5B2	0.9700
C4A—C5A	1.465 (17)	C6A—H6A2	0.9700
C4B—C5B	1.69 (3)	C6A—H6A1	0.9700
C5A—C6A	1.489 (8)	C6B—H6B1	0.9700
C5B—C6B	1.514 (16)	C6B—H6B2	0.9700
C2A—H2A1	0.9700
C1—N2—C2A	119.73 (19)	C4A—C3A—H3A2	111.00
C1—N2—C6A	118.6 (3)	C2A—C3A—H3A1	111.00
C1—N2—C2B	121.2 (2)	C4B—C3B—H3B2	110.00
C1—N2—C6B	122.8 (3)	C2B—C3B—H3B1	110.00
C2A—N2—C6A	112.6 (3)	C2B—C3B—H3B2	110.00
C2B—N2—C6B	105.9 (4)	C4B—C3B—H3B1	110.00
H1—N1—H2	109 (3)	H3B1—C3B—H3B2	109.00
H1—N1—H3	110 (3)	C3A—C4A—H4A1	110.00
H1—N1—H4	111 (3)	C3A—C4A—H4A2	110.00
H2—N1—H3	102 (2)	C5A—C4A—H4A2	110.00
H2—N1—H4	114 (3)	H4A1—C4A—H4A2	109.00
H3—N1—H4	110 (3)	C5A—C4A—H4A1	110.00
S2—C1—N2	120.70 (13)	C5B—C4B—H4B1	112.00
S1—C1—S2	118.40 (9)	H4B1—C4B—H4B2	110.00
S1—C1—N2	120.91 (13)	C3B—C4B—H4B2	111.00
N2—C2A—C3A	107.5 (3)	C5B—C4B—H4B2	112.00
N2—C2B—C3B	105.0 (5)	C3B—C4B—H4B1	112.00
C2A—C3A—C4A	103.6 (7)	C6A—C5A—H5A2	109.00
C2B—C3B—C4B	106.9 (12)	C4A—C5A—H5A1	109.00
C3A—C4A—C5A	106.5 (10)	C4A—C5A—H5A2	109.00
C3B—C4B—C5B	100.4 (15)	C6A—C5A—H5A1	109.00
C4A—C5A—C6A	111.3 (8)	H5A1—C5A—H5A2	108.00
C4B—C5B—C6B	104.9 (12)	C4B—C5B—H5B2	111.00
N2—C6A—C5A	110.3 (5)	C6B—C5B—H5B1	111.00
N2—C6B—C5B	101.5 (7)	C4B—C5B—H5B1	111.00
C3A—C2A—H2A2	110.00	H5B1—C5B—H5B2	109.00
N2—C2A—H2A1	110.00	C6B—C5B—H5B2	111.00
N2—C2A—H2A2	110.00	N2—C6A—H6A2	110.00
C3A—C2A—H2A1	110.00	C5A—C6A—H6A1	110.00
H2A1—C2A—H2A2	108.00	H6A1—C6A—H6A2	108.00
N2—C2B—H2B1	111.00	C5A—C6A—H6A2	110.00
N2—C2B—H2B2	111.00	N2—C6A—H6A1	110.00
C3B—C2B—H2B2	111.00	H6B1—C6B—H6B2	109.00
H2B1—C2B—H2B2	109.00	N2—C6B—H6B1	111.00
C3B—C2B—H2B1	111.00	N2—C6B—H6B2	112.00
C4A—C3A—H3A1	111.00	C5B—C6B—H6B1	111.00
H3A1—C3A—H3A2	109.00	C5B—C6B—H6B2	111.00
C2A—C3A—H3A2	111.00
C2A—N2—C1—S1	17.9 (4)	C1—N2—C6A—C5A	159.2 (4)
C2A—N2—C1—S2	−161.9 (3)	C2A—N2—C6A—C5A	−53.7 (6)
C6A—N2—C1—S1	162.6 (4)	N2—C2A—C3A—C4A	−65.1 (8)
C6A—N2—C1—S2	−17.3 (4)	C2A—C3A—C4A—C5A	68.2 (10)
C1—N2—C2A—C3A	−152.3 (4)	C3A—C4A—C5A—C6A	−64.0 (11)
C6A—N2—C2A—C3A	61.1 (6)	C4A—C5A—C6A—N2	56.6 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S2i	0.78 (3)	2.64 (3)	3.4029 (19)	167 (2)
N1—H2···S1	0.89 (3)	2.49 (3)	3.3565 (19)	164 (2)
N1—H3···S1ii	0.93 (3)	2.51 (3)	3.3967 (19)	159 (2)
N1—H4···S2iii	0.89 (3)	2.48 (3)	3.3632 (19)	170 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S2i	0.78 (3)	2.64 (3)	3.4029 (19)	167 (2)
N1—H2⋯S1	0.89 (3)	2.49 (3)	3.3565 (19)	164 (2)
N1—H3⋯S1ii	0.93 (3)	2.51 (3)	3.3967 (19)	159 (2)
N1—H4⋯S2iii	0.89 (3)	2.48 (3)	3.3632 (19)	170 (3)

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