4-Methyl-1-[4-(methyl-sulfan-yl)benzyl-idene]thio-semicarbazide.

The title compound, C(10)H(13)N(3)S(2), is roughly planar (r.m.s. deviation = 0.086 Å). In the crystal, N-H⋯S hydrogen bonds link the mol-ecules into (001) sheets.

Related literature

For a related structure, see: Li & Jian (2010 ▶).

Experimental

Crystal data

C10H13N3S2

M = 239.35

Monoclinic,

a = 14.123 (3) Å

b = 7.7789 (16) Å

c = 21.384 (4) Å

β = 96.31 (3)°

V = 2335.1 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.43 mm−1

T = 293 K

0.23 × 0.18 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer

10756 measured reflections

2680 independent reflections

2368 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.170

S = 1.35

2680 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811028029/hb5903sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028029/hb5903Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028029/hb5903Isup3.cml

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

C10H13N3S2	F(000) = 1008
Mr = 239.35	Dx = 1.362 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.123 (3) Å	Cell parameters from 2368 reflections
b = 7.7789 (16) Å	θ = 2.9–27.5°
c = 21.384 (4) Å	µ = 0.43 mm−1
β = 96.31 (3)°	T = 293 K
V = 2335.1 (8) Å3	Bar, colorless
Z = 8	0.23 × 0.18 × 0.17 mm

Bruker SMART CCD diffractometer	2368 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.043
graphite	θmax = 27.5°, θmin = 3.0°
phi and ω scans	h = −18→18
10756 measured reflections	k = −10→10
2680 independent reflections	l = −27→27

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170	H-atom parameters constrained
S = 1.35	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
2680 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.71 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S2	0.62610 (3)	0.59132 (7)	0.31409 (2)	0.0160 (2)
S1	0.65713 (4)	−0.10944 (9)	−0.11046 (3)	0.0285 (2)
N3	0.59872 (11)	0.4593 (3)	0.19951 (7)	0.0165 (4)
H3A	0.5447	0.5113	0.1957	0.020*
N2	0.62552 (12)	0.3592 (2)	0.15110 (7)	0.0170 (4)
N1	0.74248 (12)	0.3948 (3)	0.25443 (8)	0.0180 (4)
H1A	0.7538	0.3359	0.2221	0.022*
C9	0.65908 (13)	0.4741 (3)	0.25306 (9)	0.0152 (4)
C2	0.62751 (14)	0.0364 (3)	−0.05305 (9)	0.0189 (4)
C5	0.59070 (13)	0.2501 (3)	0.04735 (8)	0.0156 (4)
C7	0.69010 (14)	0.0413 (3)	0.00246 (9)	0.0203 (5)
H7A	0.7441	−0.0280	0.0063	0.024*
C3	0.54653 (14)	0.1405 (3)	−0.05812 (9)	0.0191 (4)
H3B	0.5048	0.1399	−0.0949	0.023*
C6	0.67274 (13)	0.1475 (3)	0.05149 (9)	0.0181 (4)
H6A	0.7158	0.1510	0.0876	0.022*
C8	0.56888 (13)	0.3578 (3)	0.09981 (9)	0.0166 (4)
H8A	0.5142	0.4253	0.0961	0.020*
C10	0.81565 (14)	0.4023 (3)	0.30768 (9)	0.0197 (5)
H10A	0.8697	0.3356	0.2986	0.030*
H10B	0.7909	0.3565	0.3443	0.030*
H10C	0.8347	0.5195	0.3153	0.030*
C4	0.52844 (13)	0.2450 (3)	−0.00809 (9)	0.0185 (4)
H4A	0.4739	0.3127	−0.0116	0.022*
C1	0.56946 (16)	−0.0720 (3)	−0.17628 (10)	0.0233 (5)
H1B	0.5809	−0.1476	−0.2101	0.035*
H1C	0.5735	0.0452	−0.1899	0.035*
H1D	0.5071	−0.0934	−0.1641	0.035*

	U11	U22	U33	U12	U13	U23
S2	0.0166 (3)	0.0151 (3)	0.0165 (3)	−0.00181 (16)	0.0024 (2)	−0.00314 (17)
S1	0.0262 (4)	0.0342 (4)	0.0247 (3)	0.0075 (2)	0.0007 (2)	−0.0115 (2)
N3	0.0154 (8)	0.0176 (10)	0.0163 (8)	0.0021 (6)	0.0008 (6)	−0.0041 (7)
N2	0.0205 (8)	0.0147 (10)	0.0163 (8)	−0.0016 (7)	0.0041 (6)	−0.0018 (7)
N1	0.0169 (8)	0.0198 (11)	0.0170 (8)	0.0007 (6)	0.0009 (6)	−0.0052 (6)
C9	0.0168 (9)	0.0116 (11)	0.0172 (9)	−0.0041 (7)	0.0026 (6)	0.0002 (7)
C2	0.0205 (10)	0.0183 (12)	0.0184 (9)	−0.0014 (8)	0.0046 (7)	−0.0013 (8)
C5	0.0206 (9)	0.0118 (11)	0.0147 (8)	−0.0031 (7)	0.0035 (6)	0.0016 (7)
C7	0.0170 (9)	0.0220 (13)	0.0220 (10)	0.0012 (8)	0.0031 (7)	−0.0003 (8)
C3	0.0208 (10)	0.0200 (13)	0.0161 (9)	−0.0015 (8)	−0.0003 (7)	0.0002 (8)
C6	0.0187 (10)	0.0185 (12)	0.0168 (9)	−0.0018 (8)	0.0008 (7)	0.0009 (8)
C8	0.0179 (9)	0.0145 (12)	0.0175 (9)	−0.0015 (7)	0.0021 (7)	0.0006 (8)
C10	0.0157 (10)	0.0222 (13)	0.0207 (10)	−0.0005 (7)	−0.0008 (7)	−0.0020 (8)
C4	0.0198 (10)	0.0165 (12)	0.0190 (9)	0.0011 (7)	0.0009 (7)	0.0026 (8)
C1	0.0310 (11)	0.0201 (13)	0.0194 (10)	−0.0045 (8)	0.0049 (8)	−0.0019 (8)

S2—C9	1.699 (2)	C5—C8	1.460 (3)
S1—C2	1.756 (2)	C7—C6	1.378 (3)
S1—C1	1.793 (2)	C7—H7A	0.9300
N3—C9	1.355 (2)	C3—C4	1.389 (3)
N3—N2	1.381 (2)	C3—H3B	0.9300
N3—H3A	0.8600	C6—H6A	0.9300
N2—C8	1.285 (2)	C8—H8A	0.9300
N1—C9	1.327 (3)	C10—H10A	0.9600
N1—C10	1.452 (3)	C10—H10B	0.9600
N1—H1A	0.8600	C10—H10C	0.9600
C2—C3	1.396 (3)	C4—H4A	0.9300
C2—C7	1.401 (3)	C1—H1B	0.9600
C5—C4	1.397 (3)	C1—H1C	0.9600
C5—C6	1.402 (3)	C1—H1D	0.9600
C2—S1—C1	104.29 (10)	C2—C3—H3B	120.1
C9—N3—N2	118.85 (16)	C7—C6—C5	120.56 (17)
C9—N3—H3A	120.6	C7—C6—H6A	119.7
N2—N3—H3A	120.6	C5—C6—H6A	119.7
C8—N2—N3	116.64 (17)	N2—C8—C5	119.77 (18)
C9—N1—C10	123.52 (17)	N2—C8—H8A	120.1
C9—N1—H1A	118.2	C5—C8—H8A	120.1
C10—N1—H1A	118.2	N1—C10—H10A	109.5
N1—C9—N3	116.98 (18)	N1—C10—H10B	109.5
N1—C9—S2	123.37 (15)	H10A—C10—H10B	109.5
N3—C9—S2	119.65 (15)	N1—C10—H10C	109.5
C3—C2—C7	119.05 (19)	H10A—C10—H10C	109.5
C3—C2—S1	125.22 (15)	H10B—C10—H10C	109.5
C7—C2—S1	115.70 (16)	C3—C4—C5	121.24 (18)
C4—C5—C6	118.41 (17)	C3—C4—H4A	119.4
C4—C5—C8	120.17 (17)	C5—C4—H4A	119.4
C6—C5—C8	121.41 (17)	S1—C1—H1B	109.5
C6—C7—C2	120.85 (19)	S1—C1—H1C	109.5
C6—C7—H7A	119.6	H1B—C1—H1C	109.5
C2—C7—H7A	119.6	S1—C1—H1D	109.5
C4—C3—C2	119.87 (18)	H1B—C1—H1D	109.5
C4—C3—H3B	120.1	H1C—C1—H1D	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···S2i	0.86	2.48	3.3195 (17)	166
N1—H1A···S2ii	0.86	2.72	3.430 (2)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯S2i	0.86	2.48	3.3195 (17)	166
N1—H1A⋯S2ii	0.86	2.72	3.430 (2)	141

Symmetry codes: (i) ; (ii) .