[(Methyl-carbamothio-yl)disulfan-yl]methyl N-methyl-carbamodithio-ate.

The title compound, C(5)H(10)N(2)S(5), was unintentionally obtained as the product of an attempted synthesis of a methyl-carbamodithioic acid using methyl-amine and carbon disulfide. In the mol-ecule, two dithio-carbamate groups are bridged by a -CH(2)S- unit. The C-S-S-C torsion angle is -90.13 (11)°. The crystal structure is stabilized by N-H⋯S inter-actions between neighbouring mol-ecules. An intra-molecular N-H⋯S hydrogen bond also occurs.

Related literature

For dithio­carbamate ligands, see: Cox et al. (1999 ▶); Liu & Bao (2007 ▶); Nair et al. (2002 ▶).

Experimental

Crystal data

C5H10N2S5

M = 258.45

Triclinic,

a = 7.188 (1) Å

b = 7.884 (2) Å

c = 10.219 (2) Å

α = 101.23 (3)°

β = 96.85 (3)°

γ = 102.74 (3)°

V = 546.0 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.01 mm−1

T = 293 K

0.30 × 0.11 × 0.10 mm

Data collection

Stoe IPDS diffractometer

4080 measured reflections

2077 independent reflections

1924 reflections with I > 2σ(I)

R int = 0.101

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.103

S = 1.15

2077 reflections

111 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.37 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-RED32 (Stoe & Cie, 2002 ▶); data reduction: X-RED32; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2007 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681003833X/om2358sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003833X/om2358Isup2.hkl

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

C5H10N2S5	V = 546.0 (2) Å3
Mr = 258.45	Z = 2
Triclinic, P1	F(000) = 268
a = 7.188 (1) Å	Dx = 1.572 Mg m−3
b = 7.884 (2) Å	Mo Kα radiation, λ = 0.71073 Å
c = 10.219 (2) Å	µ = 1.01 mm−1
α = 101.23 (3)°	T = 293 K
β = 96.85 (3)°	Needle, yellow
γ = 102.74 (3)°	0.30 × 0.11 × 0.10 mm

Stoe IPDS diffractometer	1924 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.101
graphite	θmax = 26.4°, θmin = 4.1°
ω scans	h = −8→8
4080 measured reflections	k = −9→9
2077 independent reflections	l = −12→12

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.0496P)2 + 0.0335P] where P = (Fo2 + 2Fc2)/3
2077 reflections	(Δ/σ)max = 0.001
111 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.37 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
S1	0.24777 (9)	0.73176 (9)	0.11879 (5)	0.04736 (19)
S2	0.39011 (7)	0.69015 (8)	0.38202 (5)	0.03952 (18)
S3	0.28393 (7)	0.64232 (7)	0.55098 (5)	0.03611 (17)
S4	0.22813 (8)	0.85040 (8)	0.80525 (5)	0.04221 (18)
S5	−0.14480 (9)	0.82971 (9)	0.62019 (6)	0.04559 (19)
N1	0.0187 (3)	0.6694 (2)	0.30088 (18)	0.0370 (4)
H1	0.0090	0.6510	0.3803	0.044*
N2	−0.1092 (3)	0.7742 (3)	0.86906 (19)	0.0440 (5)
H2	−0.0358	0.7639	0.9384	0.053*
C1	−0.1562 (3)	0.6703 (4)	0.2139 (3)	0.0485 (6)
H1A	−0.1370	0.7799	0.1837	0.073*
H1B	−0.2619	0.6604	0.2634	0.073*
H1C	−0.1851	0.5713	0.1369	0.073*
C2	0.1897 (3)	0.6948 (3)	0.26569 (19)	0.0333 (4)
C3	0.3067 (3)	0.8671 (3)	0.6478 (2)	0.0390 (5)
H3A	0.4402	0.9359	0.6636	0.047*
H3B	0.2275	0.9267	0.5983	0.047*
C4	−0.0280 (3)	0.8118 (3)	0.7646 (2)	0.0346 (4)
C5	−0.3151 (3)	0.7494 (4)	0.8732 (3)	0.0488 (6)
H5A	−0.3432	0.8638	0.8978	0.073*
H5B	−0.3498	0.6812	0.9388	0.073*
H5C	−0.3881	0.6867	0.7856	0.073*

	U11	U22	U33	U12	U13	U23
S1	0.0507 (4)	0.0674 (4)	0.0306 (3)	0.0158 (3)	0.0153 (2)	0.0206 (3)
S2	0.0326 (3)	0.0578 (4)	0.0331 (3)	0.0132 (2)	0.0107 (2)	0.0168 (3)
S3	0.0393 (3)	0.0427 (3)	0.0300 (3)	0.0103 (2)	0.0079 (2)	0.0157 (2)
S4	0.0366 (3)	0.0623 (4)	0.0270 (3)	0.0115 (3)	0.0030 (2)	0.0107 (3)
S5	0.0446 (3)	0.0627 (4)	0.0328 (3)	0.0181 (3)	0.0012 (2)	0.0168 (3)
N1	0.0357 (9)	0.0483 (10)	0.0304 (8)	0.0113 (8)	0.0081 (7)	0.0145 (8)
N2	0.0385 (10)	0.0645 (12)	0.0333 (9)	0.0154 (9)	0.0056 (8)	0.0187 (9)
C1	0.0379 (13)	0.0657 (15)	0.0452 (12)	0.0161 (11)	0.0032 (10)	0.0193 (12)
C2	0.0388 (11)	0.0358 (9)	0.0276 (9)	0.0105 (8)	0.0077 (8)	0.0104 (8)
C3	0.0413 (11)	0.0417 (11)	0.0331 (10)	0.0045 (9)	0.0093 (9)	0.0116 (9)
C4	0.0385 (11)	0.0382 (10)	0.0290 (9)	0.0136 (8)	0.0061 (8)	0.0073 (8)
C5	0.0395 (13)	0.0686 (16)	0.0417 (12)	0.0180 (12)	0.0101 (10)	0.0137 (12)

S1—C2	1.6671 (18)	N2—C5	1.456 (3)
S2—C2	1.767 (2)	N2—H2	0.8600
S2—S3	2.0364 (8)	C1—H1A	0.9600
S3—C3	1.816 (2)	C1—H1B	0.9600
S4—C4	1.782 (2)	C1—H1C	0.9600
S4—C3	1.787 (2)	C3—H3A	0.9700
S5—C4	1.655 (2)	C3—H3B	0.9700
N1—C2	1.306 (3)	C5—H5A	0.9600
N1—C1	1.453 (3)	C5—H5B	0.9600
N1—H1	0.8600	C5—H5C	0.9600
N2—C4	1.328 (3)
C2—S2—S3	105.99 (7)	S1—C2—S2	113.24 (12)
C3—S3—S2	101.85 (7)	S4—C3—S3	107.88 (10)
C4—S4—C3	103.25 (10)	S4—C3—H3A	110.1
C2—N1—C1	123.90 (17)	S3—C3—H3A	110.1
C2—N1—H1	118.0	S4—C3—H3B	110.1
C1—N1—H1	118.0	S3—C3—H3B	110.1
C4—N2—C5	123.93 (18)	H3A—C3—H3B	108.4
C4—N2—H2	118.0	N2—C4—S5	125.43 (17)
C5—N2—H2	118.0	N2—C4—S4	109.93 (14)
N1—C1—H1A	109.5	S5—C4—S4	124.59 (12)
N1—C1—H1B	109.5	N2—C5—H5A	109.5
H1A—C1—H1B	109.5	N2—C5—H5B	109.5
N1—C1—H1C	109.5	H5A—C5—H5B	109.5
H1A—C1—H1C	109.5	N2—C5—H5C	109.5
H1B—C1—H1C	109.5	H5A—C5—H5C	109.5
N1—C2—S1	127.70 (16)	H5B—C5—H5C	109.5
N1—C2—S2	119.06 (14)
C2—S2—S3—C3	−90.13 (11)	S2—S3—C3—S4	−177.57 (9)
C1—N1—C2—S1	−0.4 (3)	C5—N2—C4—S5	−2.4 (3)
C1—N1—C2—S2	179.97 (18)	C5—N2—C4—S4	175.1 (2)
S3—S2—C2—N1	−0.01 (19)	C3—S4—C4—N2	172.23 (16)
S3—S2—C2—S1	−179.71 (9)	C3—S4—C4—S5	−10.31 (17)
C4—S4—C3—S3	−83.86 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S3	0.86	2.50	3.073 (2)	125
N1—H1···S3i	0.86	3.02	3.595 (2)	127
N2—H2···S1ii	0.86	2.67	3.515 (2)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S3	0.86	2.50	3.073 (2)	125
N1—H1⋯S3i	0.86	3.02	3.595 (2)	127
N2—H2⋯S1ii	0.86	2.67	3.515 (2)	168

Symmetry codes: (i) ; (ii) .