(Pyridin-4-yl)methyl N'-(3-phenyl-allyl-idene)hydrazinecarbodithio-ate.

In the title compound, C(16)H(15)N(3)S(2), the central C(2)N(2)S(2) residue is planar (r.m.s. deviation = 0.045 Å) and the pyridyl and benzene rings are inclined and approximately coplanar to this plane, respectively [dihedral angles = 72.85 (9) and 10.73 (9)°], so that, overall, the mol-ecule adopts an L-shape. The conformation about each of the N=C [1.290 (3) Å] and C=C [1.340 (3) Å] bonds is E. Supra-molecular chains along [1-10] are stabilized by N-H⋯N(pyridine) hydrogen bonding and these are connected into a double layer that stacks along the c-axis direction by C-H⋯π(pyridine) inter-actions.

Related literature

For background to related Schiff bases of S-substituted dithio­carbaza­tes with cinnamaldehyde, see: Tarafder et al. (2008 ▶, 2010 ▶). For the corresponding metal complexes, see: Reza et al. (2012 ▶); Liu et al. (2009 ▶). For the biological activity of similar sulfur–nitro­gen-containing Schiff base derivatives, see: Maia et al. (2010 ▶); Pavan et al. (2010 ▶); Zhu et al. (2009 ▶). For the synthesis, see: Crouse et al. (2004 ▶); Khoo (2008 ▶); Tarafder et al. (2008 ▶, 2010 ▶).

Experimental

Crystal data

C16H15N3S2

M = 313.43

Triclinic,

a = 5.3784 (5) Å

b = 10.1570 (9) Å

c = 14.5488 (17) Å

α = 77.315 (9)°

β = 84.735 (9)°

γ = 78.193 (8)°

V = 758.06 (13) Å3

Z = 2

Cu Kα radiation

μ = 3.14 mm−1

T = 100 K

0.13 × 0.06 × 0.01 mm

Data collection

Oxford Diffraction Xcaliber Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.83, T max = 0.97

15664 measured reflections

2918 independent reflections

2469 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.115

S = 1.05

2918 reflections

193 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2012 ▶) and DIAMOND (Brandenburg, 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/S1600536812051537/qm2090sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051537/qm2090Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051537/qm2090Isup3.cml

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

C16H15N3S2	Z = 2
Mr = 313.43	F(000) = 328
Triclinic, P1	Dx = 1.373 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 5.3784 (5) Å	Cell parameters from 5833 reflections
b = 10.1570 (9) Å	θ = 3–72°
c = 14.5488 (17) Å	µ = 3.14 mm−1
α = 77.315 (9)°	T = 100 K
β = 84.735 (9)°	Thin-plate, orange
γ = 78.193 (8)°	0.13 × 0.06 × 0.01 mm
V = 758.06 (13) Å3

Oxford Diffraction Xcaliber Eos Gemini diffractometer	2918 independent reflections
Radiation source: fine-focus sealed tube	2469 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 16.1952 pixels mm-1	θmax = 72.3°, θmin = 3.1°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −12→12
Tmin = 0.83, Tmax = 0.97	l = −17→15
15664 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0669P)2 + 0.3038P] where P = (Fo2 + 2Fc2)/3
2918 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.42 e Å−3
1 restraint	Δρmin = −0.29 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.36876 (9)	0.53086 (5)	0.18295 (4)	0.02532 (16)
S2	0.33320 (10)	0.32045 (5)	0.06781 (4)	0.02701 (17)
N1	0.6775 (3)	0.29601 (17)	0.19095 (13)	0.0256 (4)
H1n	0.749 (4)	0.2148 (14)	0.1794 (18)	0.031*
N2	0.7786 (3)	0.34184 (17)	0.25917 (13)	0.0262 (4)
N3	−0.1177 (4)	1.01818 (18)	0.16683 (15)	0.0338 (5)
C1	0.4717 (4)	0.3730 (2)	0.14713 (15)	0.0233 (4)
C2	0.9846 (4)	0.2638 (2)	0.29282 (16)	0.0266 (5)
H2	1.0579	0.1846	0.2682	0.032*
C3	1.1038 (4)	0.2962 (2)	0.36748 (16)	0.0284 (5)
H3	1.0295	0.3764	0.3909	0.034*
C4	1.3162 (4)	0.2171 (2)	0.40512 (16)	0.0279 (5)
H4	1.3893	0.1405	0.3776	0.033*
C5	1.4484 (4)	0.2350 (2)	0.48372 (16)	0.0284 (5)
C6	1.3649 (5)	0.3430 (2)	0.53137 (18)	0.0370 (6)
H6	1.2139	0.4074	0.5133	0.044*
C7	1.4982 (5)	0.3574 (3)	0.60420 (19)	0.0393 (6)
H7	1.4401	0.4323	0.6349	0.047*
C8	1.7160 (5)	0.2633 (3)	0.63253 (18)	0.0368 (6)
H8	1.8074	0.2733	0.6826	0.044*
C9	1.8000 (4)	0.1543 (3)	0.58746 (18)	0.0359 (5)
H9	1.9484	0.0889	0.6072	0.043*
C10	1.6683 (4)	0.1405 (2)	0.51347 (17)	0.0312 (5)
H10	1.7283	0.0659	0.4827	0.037*
C11	0.1118 (4)	0.6125 (2)	0.10459 (17)	0.0269 (5)
H11A	0.1725	0.6164	0.0379	0.032*
H11B	−0.0298	0.5612	0.1181	0.032*
C12	0.0263 (4)	0.7559 (2)	0.12385 (16)	0.0262 (5)
C13	−0.1950 (4)	0.7908 (2)	0.17696 (19)	0.0357 (6)
H13	−0.3022	0.7258	0.1998	0.043*
C14	−0.2588 (4)	0.9219 (2)	0.1965 (2)	0.0390 (6)
H14	−0.4112	0.9441	0.2330	0.047*
C15	0.0961 (5)	0.9839 (2)	0.11574 (18)	0.0345 (5)
H15	0.1999	1.0508	0.0940	0.041*
C16	0.1742 (4)	0.8555 (2)	0.09283 (17)	0.0314 (5)
H16	0.3277	0.8361	0.0562	0.038*

	U11	U22	U33	U12	U13	U23
S1	0.0270 (3)	0.0170 (3)	0.0333 (3)	0.00106 (19)	−0.0078 (2)	−0.0104 (2)
S2	0.0278 (3)	0.0215 (3)	0.0342 (3)	−0.0011 (2)	−0.0060 (2)	−0.0124 (2)
N1	0.0275 (9)	0.0184 (8)	0.0315 (10)	0.0004 (7)	−0.0035 (8)	−0.0100 (7)
N2	0.0260 (9)	0.0226 (9)	0.0312 (10)	−0.0014 (7)	−0.0049 (7)	−0.0095 (7)
N3	0.0309 (10)	0.0233 (9)	0.0484 (13)	0.0048 (7)	−0.0124 (9)	−0.0149 (9)
C1	0.0249 (10)	0.0176 (9)	0.0272 (11)	−0.0021 (8)	0.0002 (8)	−0.0062 (8)
C2	0.0251 (10)	0.0224 (10)	0.0323 (12)	−0.0021 (8)	−0.0013 (9)	−0.0078 (9)
C3	0.0292 (11)	0.0234 (10)	0.0334 (12)	−0.0025 (8)	−0.0023 (9)	−0.0096 (9)
C4	0.0300 (11)	0.0238 (10)	0.0299 (12)	−0.0020 (8)	0.0003 (9)	−0.0089 (9)
C5	0.0271 (11)	0.0262 (11)	0.0313 (12)	−0.0045 (8)	−0.0021 (9)	−0.0051 (9)
C6	0.0370 (13)	0.0302 (12)	0.0429 (15)	0.0047 (9)	−0.0111 (11)	−0.0122 (10)
C7	0.0419 (14)	0.0341 (13)	0.0436 (15)	0.0009 (10)	−0.0083 (11)	−0.0166 (11)
C8	0.0345 (12)	0.0433 (14)	0.0341 (13)	−0.0045 (10)	−0.0093 (10)	−0.0111 (11)
C9	0.0281 (11)	0.0395 (13)	0.0387 (14)	0.0020 (9)	−0.0057 (10)	−0.0111 (11)
C10	0.0291 (11)	0.0303 (11)	0.0339 (13)	−0.0007 (9)	−0.0007 (9)	−0.0108 (9)
C11	0.0268 (10)	0.0201 (10)	0.0344 (12)	0.0004 (8)	−0.0097 (9)	−0.0077 (9)
C12	0.0270 (10)	0.0198 (10)	0.0320 (12)	0.0022 (8)	−0.0113 (9)	−0.0081 (8)
C13	0.0260 (11)	0.0314 (12)	0.0542 (16)	−0.0051 (9)	−0.0020 (10)	−0.0185 (11)
C14	0.0257 (11)	0.0359 (13)	0.0584 (17)	0.0018 (9)	−0.0017 (11)	−0.0235 (12)
C15	0.0389 (13)	0.0204 (10)	0.0439 (14)	−0.0034 (9)	−0.0068 (11)	−0.0060 (9)
C16	0.0328 (11)	0.0230 (10)	0.0363 (13)	0.0005 (9)	−0.0022 (10)	−0.0071 (9)

S1—C1	1.760 (2)	C7—C8	1.383 (3)
S1—C11	1.817 (2)	C7—H7	0.9500
S2—C1	1.662 (2)	C8—C9	1.385 (4)
N1—C1	1.342 (3)	C8—H8	0.9500
N1—N2	1.379 (3)	C9—C10	1.389 (3)
N1—H1n	0.880 (10)	C9—H9	0.9500
N2—C2	1.290 (3)	C10—H10	0.9500
N3—C14	1.332 (3)	C11—C12	1.514 (3)
N3—C15	1.337 (3)	C11—H11A	0.9900
C2—C3	1.439 (3)	C11—H11B	0.9900
C2—H2	0.9500	C12—C13	1.385 (3)
C3—C4	1.340 (3)	C12—C16	1.386 (3)
C3—H3	0.9500	C13—C14	1.391 (3)
C4—C5	1.463 (3)	C13—H13	0.9500
C4—H4	0.9500	C14—H14	0.9500
C5—C10	1.398 (3)	C15—C16	1.389 (3)
C5—C6	1.400 (3)	C15—H15	0.9500
C6—C7	1.382 (3)	C16—H16	0.9500
C6—H6	0.9500
C1—S1—C11	101.51 (10)	C9—C8—H8	120.2
C1—N1—N2	119.67 (17)	C8—C9—C10	120.2 (2)
C1—N1—H1n	122.4 (17)	C8—C9—H9	119.9
N2—N1—H1n	117.9 (17)	C10—C9—H9	119.9
C2—N2—N1	114.56 (18)	C9—C10—C5	120.9 (2)
C14—N3—C15	116.84 (19)	C9—C10—H10	119.6
N1—C1—S2	121.98 (16)	C5—C10—H10	119.6
N1—C1—S1	113.13 (16)	C12—C11—S1	105.44 (14)
S2—C1—S1	124.88 (12)	C12—C11—H11A	110.7
N2—C2—C3	120.4 (2)	S1—C11—H11A	110.7
N2—C2—H2	119.8	C12—C11—H11B	110.7
C3—C2—H2	119.8	S1—C11—H11B	110.7
C4—C3—C2	122.2 (2)	H11A—C11—H11B	108.8
C4—C3—H3	118.9	C13—C12—C16	117.4 (2)
C2—C3—H3	118.9	C13—C12—C11	121.6 (2)
C3—C4—C5	127.5 (2)	C16—C12—C11	121.0 (2)
C3—C4—H4	116.3	C12—C13—C14	119.3 (2)
C5—C4—H4	116.3	C12—C13—H13	120.3
C10—C5—C6	117.9 (2)	C14—C13—H13	120.3
C10—C5—C4	119.1 (2)	N3—C14—C13	123.6 (2)
C6—C5—C4	123.0 (2)	N3—C14—H14	118.2
C7—C6—C5	121.1 (2)	C13—C14—H14	118.2
C7—C6—H6	119.4	N3—C15—C16	123.4 (2)
C5—C6—H6	119.4	N3—C15—H15	118.3
C6—C7—C8	120.2 (2)	C16—C15—H15	118.3
C6—C7—H7	119.9	C12—C16—C15	119.4 (2)
C8—C7—H7	119.9	C12—C16—H16	120.3
C7—C8—C9	119.7 (2)	C15—C16—H16	120.3
C7—C8—H8	120.2
C1—N1—N2—C2	−176.15 (19)	C8—C9—C10—C5	−0.5 (4)
N2—N1—C1—S2	−177.22 (15)	C6—C5—C10—C9	−0.5 (3)
N2—N1—C1—S1	2.5 (2)	C4—C5—C10—C9	179.6 (2)
C11—S1—C1—N1	175.41 (16)	C1—S1—C11—C12	−174.77 (15)
C11—S1—C1—S2	−4.84 (16)	S1—C11—C12—C13	−103.5 (2)
N1—N2—C2—C3	−177.19 (18)	S1—C11—C12—C16	73.2 (2)
N2—C2—C3—C4	179.2 (2)	C16—C12—C13—C14	0.1 (4)
C2—C3—C4—C5	−176.9 (2)	C11—C12—C13—C14	176.9 (2)
C3—C4—C5—C10	179.6 (2)	C15—N3—C14—C13	−0.1 (4)
C3—C4—C5—C6	−0.2 (4)	C12—C13—C14—N3	0.0 (4)
C10—C5—C6—C7	1.3 (4)	C14—N3—C15—C16	0.2 (4)
C4—C5—C6—C7	−178.8 (2)	C13—C12—C16—C15	0.0 (3)
C5—C6—C7—C8	−1.1 (4)	C11—C12—C16—C15	−176.9 (2)
C6—C7—C8—C9	0.1 (4)	N3—C15—C16—C12	−0.1 (4)
C7—C8—C9—C10	0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···N3i	0.88 (2)	2.02 (2)	2.897 (3)	172 (2)
C8—H8···Cg1ii	0.95	2.92	3.701 (3)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N3,C12–C15 pyridyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯N3i	0.88 (2)	2.02 (2)	2.897 (3)	172 (2)
C8—H8⋯Cg1ii	0.95	2.92	3.701 (3)	141

Symmetry codes: (i) ; (ii) .