Benzyl N-[(Z)-(1-methyl-2-sulfanyl-propyl-idene)amino]-carbamodithio-ate.

The title compound, C(12)H(16)N(2)S(3), was obtained by the condensation reaction of S-benzyl dithio-carbazate and 3-mercaptobutan-2-one. The phenyl ring and thiol (SH) group are approximately perpendicular [S-C-C-C and N-C-C-S torsion angles = 67.8 (3) and 116.9 (2)°, respectively] to the rest of the mol-ecule. In the crystal, mol-ecules are linked by weak S-H⋯S and N-H⋯S hydrogen bonds, π-π inter-actions between the benzene rings [centroid-centroid distance = 3.823 (2) Å] and C-H⋯π inter-actions.

Related literature

For biological applications of Schiff base ligands and complexes derived from S-benzyl­dithio­carbazate, see: Hossain et al. (1996 ▶); Tarafder et al. (2002 ▶). For related structures derived from S-benzyl­dithio­carbazate, which exhibit a similar geometry to the title compound, see: Khoo et al. (2005 ▶); How et al. (2007 ▶); Shan et al. (2011 ▶). For the synthesis, see: Tarafder et al. (2002 ▶).

Experimental

Crystal data

C12H16N2S3

M = 284.47

Monoclinic,

a = 16.3887 (4) Å

b = 8.3136 (2) Å

c = 10.1404 (3) Å

β = 90.234 (2)°

V = 1381.61 (6) Å3

Z = 4

Cu Kα radiation

μ = 4.73 mm−1

T = 100 K

0.25 × 0.10 × 0.08 mm

Data collection

Oxford Diffraction Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.31, T max = 0.68

7359 measured reflections

2615 independent reflections

2374 reflections with I > 2σ(I)

R int = 0.027

Standard reflections: 0

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.123

S = 0.99

2605 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.60 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812051008/nk2192sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051008/nk2192Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051008/nk2192Isup3.mol

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051008/nk2192Isup4.cml

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

C12H16N2S3	F(000) = 600
Mr = 284.47	Dx = 1.368 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
a = 16.3887 (4) Å	Cell parameters from 3777 reflections
b = 8.3136 (2) Å	θ = 4–71°
c = 10.1404 (3) Å	µ = 4.73 mm−1
β = 90.234 (2)°	T = 100 K
V = 1381.61 (6) Å3	Plate, yellow
Z = 4	0.25 × 0.10 × 0.08 mm

Oxford Diffraction Gemini diffractometer	2374 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω scans	θmax = 71.4°, θmin = 5.4°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −19→20
Tmin = 0.31, Tmax = 0.68	k = −10→10
7359 measured reflections	l = −12→9
2615 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.123	Method = Modified Sheldrick w = 1/[σ2(F2) + ( 0.07P)2 + 2.47P], where P = (max(Fo2,0) + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
2605 reflections	Δρmax = 0.55 e Å−3
154 parameters	Δρmin = −0.60 e Å−3
0 restraints

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat with a nominal stability of 0.1 K.

	x	y	z	Uiso*/Ueq
S1	0.09283 (4)	0.86651 (8)	0.60282 (6)	0.0199
C2	0.14578 (15)	0.9210 (3)	0.4711 (3)	0.0161
S3	0.25242 (4)	0.90367 (8)	0.45582 (6)	0.0169
C4	0.28225 (15)	0.8290 (3)	0.6180 (2)	0.0188
C5	0.37460 (15)	0.8307 (3)	0.6187 (2)	0.0169
C6	0.41672 (16)	0.9417 (3)	0.6956 (3)	0.0206
C7	0.50166 (17)	0.9473 (4)	0.6929 (3)	0.0225
C8	0.54462 (16)	0.8430 (4)	0.6130 (3)	0.0219
C9	0.50291 (16)	0.7324 (3)	0.5353 (3)	0.0214
C10	0.41832 (16)	0.7260 (3)	0.5382 (3)	0.0197
N11	0.11068 (12)	0.9875 (3)	0.3635 (2)	0.0170
N12	0.16216 (13)	1.0374 (3)	0.2636 (2)	0.0175
C13	0.13156 (16)	1.1118 (3)	0.1648 (3)	0.0177
C14	0.19140 (16)	1.1704 (3)	0.0635 (3)	0.0204
S15	0.17221 (5)	1.07040 (10)	−0.09485 (8)	0.0330
C16	0.28359 (14)	1.1622 (3)	0.1108 (3)	0.0174
C17	0.04289 (17)	1.1502 (4)	0.1460 (3)	0.0280
H42	0.2606	0.8996	0.6857	0.0241*
H41	0.2610	0.7201	0.6290	0.0236*
H61	0.3876	1.0135	0.7489	0.0263*
H71	0.5297	1.0237	0.7454	0.0292*
H81	0.6020	0.8472	0.6120	0.0276*
H91	0.5316	0.6627	0.4815	0.0271*
H101	0.3910	0.6505	0.4850	0.0248*
H141	0.1776	1.2846	0.0485	0.0260*
H162	0.3131	1.2050	0.0476	0.0278*
H161	0.2891	1.2182	0.1858	0.0279*
H163	0.2963	1.0585	0.1218	0.0273*
H171	0.0348	1.1957	0.0604	0.0430*
H173	0.0259	1.2280	0.2111	0.0430*
H172	0.0109	1.0536	0.1544	0.0427*
H111	0.0595	1.0101	0.3634	0.0211*
H151	0.1736	0.9172	−0.0413	0.0626*

	U11	U22	U33	U12	U13	U23
S1	0.0142 (3)	0.0288 (4)	0.0167 (3)	0.0005 (2)	0.0001 (2)	0.0022 (3)
C2	0.0139 (12)	0.0171 (12)	0.0173 (12)	−0.0001 (9)	−0.0009 (9)	−0.0038 (10)
S3	0.0123 (3)	0.0223 (3)	0.0159 (3)	0.0019 (2)	−0.0009 (2)	0.0016 (2)
C4	0.0160 (12)	0.0258 (14)	0.0146 (12)	0.0025 (10)	−0.0014 (9)	0.0029 (10)
C5	0.0155 (12)	0.0223 (13)	0.0130 (11)	0.0009 (10)	−0.0014 (9)	0.0051 (10)
C6	0.0218 (13)	0.0247 (14)	0.0154 (13)	0.0034 (11)	−0.0004 (10)	0.0000 (11)
C7	0.0212 (13)	0.0281 (15)	0.0182 (13)	−0.0022 (11)	−0.0040 (10)	0.0015 (11)
C8	0.0145 (12)	0.0294 (15)	0.0219 (13)	0.0000 (11)	−0.0016 (10)	0.0051 (11)
C9	0.0201 (13)	0.0242 (14)	0.0199 (13)	0.0043 (11)	0.0027 (10)	0.0021 (11)
C10	0.0196 (12)	0.0211 (13)	0.0183 (13)	−0.0012 (10)	−0.0021 (10)	0.0005 (10)
N11	0.0113 (9)	0.0217 (11)	0.0179 (11)	0.0009 (8)	−0.0003 (8)	0.0015 (9)
N12	0.0157 (10)	0.0176 (11)	0.0191 (11)	−0.0008 (8)	0.0001 (8)	0.0009 (9)
C13	0.0179 (13)	0.0184 (12)	0.0167 (12)	0.0003 (10)	0.0001 (10)	−0.0012 (10)
C14	0.0189 (13)	0.0195 (13)	0.0229 (13)	−0.0004 (10)	−0.0007 (10)	0.0036 (11)
S15	0.0372 (4)	0.0348 (4)	0.0269 (4)	0.0010 (3)	0.0047 (3)	0.0019 (3)
C16	0.0076 (11)	0.0178 (13)	0.0269 (14)	−0.0035 (9)	0.0069 (9)	0.0070 (10)
C17	0.0201 (14)	0.0412 (18)	0.0225 (14)	0.0051 (12)	−0.0010 (11)	0.0102 (13)

S1—C2	1.659 (3)	C10—H101	0.941
C2—S3	1.761 (3)	N11—N12	1.384 (3)
C2—N11	1.350 (3)	N11—H111	0.859
S3—C4	1.823 (3)	N12—C13	1.278 (3)
C4—C5	1.514 (3)	C13—C14	1.504 (4)
C4—H42	0.972	C13—C17	1.499 (4)
C4—H41	0.976	C14—S15	1.834 (3)
C5—C6	1.390 (4)	C14—C16	1.585 (3)
C5—C10	1.393 (4)	C14—H141	0.988
C6—C7	1.393 (4)	S15—H151	1.385
C6—H61	0.937	C16—H162	0.880
C7—C8	1.382 (4)	C16—H161	0.896
C7—H71	0.947	C16—H163	0.894
C8—C9	1.389 (4)	C17—H171	0.955
C8—H81	0.941	C17—H173	0.966
C9—C10	1.388 (4)	C17—H172	0.963
C9—H91	0.926
S1—C2—S3	124.83 (15)	C9—C10—H101	119.2
S1—C2—N11	122.70 (19)	C2—N11—N12	117.1 (2)
S3—C2—N11	112.46 (19)	C2—N11—H111	120.2
C2—S3—C4	102.18 (12)	N12—N11—H111	122.1
S3—C4—C5	105.39 (17)	N11—N12—C13	118.7 (2)
S3—C4—H42	109.5	N12—C13—C14	115.9 (2)
C5—C4—H42	111.0	N12—C13—C17	125.4 (2)
S3—C4—H41	108.9	C14—C13—C17	118.6 (2)
C5—C4—H41	111.4	C13—C14—S15	109.95 (18)
H42—C4—H41	110.4	C13—C14—C16	113.7 (2)
C4—C5—C6	120.2 (2)	S15—C14—C16	113.94 (19)
C4—C5—C10	120.5 (2)	C13—C14—H141	105.5
C6—C5—C10	119.2 (2)	S15—C14—H141	105.2
C5—C6—C7	120.4 (3)	C16—C14—H141	107.8
C5—C6—H61	119.6	C14—S15—H151	94.1
C7—C6—H61	120.1	C14—C16—H162	106.7
C6—C7—C8	120.1 (3)	C14—C16—H161	109.1
C6—C7—H71	119.7	H162—C16—H161	110.7
C8—C7—H71	120.2	C14—C16—H163	107.4
C7—C8—C9	119.8 (2)	H162—C16—H163	110.6
C7—C8—H81	119.6	H161—C16—H163	112.0
C9—C8—H81	120.6	C13—C17—H171	109.3
C8—C9—C10	120.2 (3)	C13—C17—H173	109.8
C8—C9—H91	120.0	H171—C17—H173	108.4
C10—C9—H91	119.8	C13—C17—H172	109.8
C5—C10—C9	120.3 (2)	H171—C17—H172	109.7
C5—C10—H101	120.5	H173—C17—H172	109.8

D—H···A	D—H	H···A	D···A	D—H···A
S15—H151···S3i	1.38	2.96	4.186 (1)	146
N11—H111···S1ii	0.86	2.72	3.567 (2)	168
C7—H71···Cgiii	0.95	2.97	3.827 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
S15—H151⋯S3i	1.38	2.96	4.186 (1)	146
N11—H111⋯S1ii	0.86	2.72	3.567 (2)	168
C7—H71⋯Cg iii	0.95	2.97	3.827 (3)	152

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