4-Methyl-1-(3-pyridyl-methyl-idene)thio-semicarbazide.

All the non-H atoms of the title compound, C(8)H(10)N(4)S, lie on a crystallographic mirror plane and an intra-molecular N-H⋯N hydrogen bond helps to stabilize the mol-ecular conformation. In the crystal, mol-ecules are linked through inter-molecular N-H⋯N hydrogen bonds, forming zigzag C(7) chains along the a axis.

Related literature

For background to Schiff bases derived from thio­semicarbazone and its derivatives, see: Casas et al. (2001 ▶); Beraldo et al. (2001 ▶); Jouad et al. (2002 ▶); Swearingen et al. (2002 ▶). For bond-length data, see: Allen et al. (1987 ▶). For similar structures, see: Selvanayagam et al. (2002 ▶); Karakurt et al. (2003 ▶); Bernhardt et al. (2003 ▶); Sampath et al. (2003 ▶).

Experimental

Crystal data

C8H10N4S

M = 194.26

Monoclinic,

a = 7.276 (3) Å

b = 6.581 (2) Å

c = 10.297 (3) Å

β = 92.997 (2)°

V = 492.4 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.29 mm−1

T = 298 K

0.17 × 0.15 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.953, T max = 0.958

3208 measured reflections

1106 independent reflections

640 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.118

S = 1.02

1106 reflections

84 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536810048853/hb5755sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048853/hb5755Isup2.hkl

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

C8H10N4S	F(000) = 204
Mr = 194.26	Dx = 1.310 Mg m−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 669 reflections
a = 7.276 (3) Å	θ = 2.7–24.5°
b = 6.581 (2) Å	µ = 0.29 mm−1
c = 10.297 (3) Å	T = 298 K
β = 92.997 (2)°	Block, colourless
V = 492.4 (3) Å3	0.17 × 0.15 × 0.15 mm
Z = 2

Bruker APEXII CCD diffractometer	1106 independent reflections
Radiation source: fine-focus sealed tube	640 reflections with I > 2σ(I)
graphite	Rint = 0.041
ω scans	θmax = 26.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
Tmin = 0.953, Tmax = 0.958	k = −8→8
3208 measured reflections	l = −12→10

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0547P)2] where P = (Fo2 + 2Fc2)/3
1106 reflections	(Δ/σ)max < 0.001
84 parameters	Δρmax = 0.14 e Å−3
2 restraints	Δρmin = −0.19 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	0.68926 (12)	0.2500	0.29184 (9)	0.0835 (4)
N1	−0.2929 (3)	0.2500	−0.1051 (2)	0.0558 (7)
N2	0.2508 (3)	0.2500	0.0542 (2)	0.0507 (6)
N3	0.4324 (3)	0.2500	0.1009 (2)	0.0566 (7)
N4	0.3217 (4)	0.2500	0.3028 (3)	0.0699 (8)
C1	0.0350 (3)	0.2500	−0.1287 (3)	0.0496 (7)
C2	−0.1201 (3)	0.2500	−0.0547 (3)	0.0510 (8)
H2	−0.1020	0.2500	0.0354	0.061*
C3	−0.3159 (4)	0.2500	−0.2351 (3)	0.0616 (9)
H3A	−0.4353	0.2500	−0.2720	0.074*
C4	−0.1733 (4)	0.2500	−0.3164 (3)	0.0697 (10)
H4A	−0.1954	0.2500	−0.4061	0.084*
C5	0.0049 (4)	0.2500	−0.2620 (3)	0.0673 (10)
H5	0.1041	0.2500	−0.3154	0.081*
C6	0.2213 (4)	0.2500	−0.0687 (3)	0.0581 (8)
H6	0.3209	0.2500	−0.1217	0.070*
C7	0.4698 (4)	0.2500	0.2318 (3)	0.0554 (8)
C8	0.3272 (5)	0.2500	0.4451 (3)	0.0994 (13)
H8A	0.3310	0.1125	0.4762	0.149*	0.50
H8B	0.2193	0.3162	0.4743	0.149*	0.50
H8C	0.4349	0.3213	0.4781	0.149*	0.50
H3	0.519 (3)	0.2500	0.042 (2)	0.080*
H4	0.212 (2)	0.2500	0.259 (3)	0.080*

	U11	U22	U33	U12	U13	U23
S1	0.0681 (6)	0.1189 (9)	0.0617 (6)	0.000	−0.0150 (4)	0.000
N1	0.0392 (13)	0.0640 (17)	0.0642 (17)	0.000	0.0028 (12)	0.000
N2	0.0365 (12)	0.0615 (16)	0.0542 (15)	0.000	0.0019 (11)	0.000
N3	0.0416 (13)	0.0775 (18)	0.0508 (16)	0.000	0.0024 (11)	0.000
N4	0.0738 (18)	0.085 (2)	0.0518 (16)	0.000	0.0136 (14)	0.000
C1	0.0369 (14)	0.0618 (19)	0.0503 (17)	0.000	0.0058 (12)	0.000
C2	0.0425 (15)	0.0593 (19)	0.0512 (18)	0.000	0.0011 (13)	0.000
C3	0.0450 (16)	0.074 (2)	0.064 (2)	0.000	−0.0062 (15)	0.000
C4	0.0587 (19)	0.102 (3)	0.0478 (19)	0.000	−0.0054 (16)	0.000
C5	0.0505 (18)	0.097 (3)	0.055 (2)	0.000	0.0091 (15)	0.000
C6	0.0389 (15)	0.078 (2)	0.0579 (19)	0.000	0.0108 (13)	0.000
C7	0.0624 (19)	0.0541 (19)	0.0499 (18)	0.000	0.0033 (15)	0.000
C8	0.126 (3)	0.121 (4)	0.053 (2)	0.000	0.023 (2)	0.000

S1—C7	1.682 (3)	C1—C6	1.460 (4)
N1—C2	1.335 (3)	C2—H2	0.9300
N1—C3	1.340 (3)	C3—C4	1.367 (4)
N2—C6	1.273 (4)	C3—H3A	0.9300
N2—N3	1.382 (3)	C4—C5	1.385 (4)
N3—C7	1.361 (4)	C4—H4A	0.9300
N3—H3	0.899 (10)	C5—H5	0.9300
N4—C7	1.334 (4)	C6—H6	0.9300
N4—C8	1.463 (4)	C8—H8A	0.9600
N4—H4	0.898 (10)	C8—H8B	0.9600
C1—C5	1.379 (4)	C8—H8C	0.9600
C1—C2	1.394 (4)
C2—N1—C3	117.0 (2)	C3—C4—H4A	120.8
C6—N2—N3	117.1 (2)	C5—C4—H4A	120.8
C7—N3—N2	118.9 (2)	C1—C5—C4	119.9 (3)
C7—N3—H3	124 (2)	C1—C5—H5	120.0
N2—N3—H3	117 (2)	C4—C5—H5	120.0
C7—N4—C8	124.7 (3)	N2—C6—C1	121.7 (3)
C7—N4—H4	117 (2)	N2—C6—H6	119.2
C8—N4—H4	119 (2)	C1—C6—H6	119.2
C5—C1—C2	117.0 (2)	N4—C7—N3	114.7 (3)
C5—C1—C6	121.1 (3)	N4—C7—S1	125.2 (2)
C2—C1—C6	121.9 (3)	N3—C7—S1	120.1 (2)
N1—C2—C1	124.1 (2)	N4—C8—H8A	109.5
N1—C2—H2	118.0	N4—C8—H8B	109.5
C1—C2—H2	118.0	H8A—C8—H8B	109.5
N1—C3—C4	123.6 (3)	N4—C8—H8C	109.5
N1—C3—H3A	118.2	H8A—C8—H8C	109.5
C4—C3—H3A	118.2	H8B—C8—H8C	109.5
C3—C4—C5	118.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N2	0.90 (2)	2.14 (3)	2.585 (4)	109 (2)
N3—H3···N1i	0.90 (1)	2.09 (1)	2.989 (3)	176 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯N2	0.90 (2)	2.14 (3)	2.585 (4)	109 (2)
N3—H3⋯N1i	0.90 (1)	2.09 (1)	2.989 (3)	176 (3)

Symmetry code: (i) .