1,2-Bis[1-(3-methyl-sulfanyl-1,2,4-triazin-5-yl)ethyl-idene]diazane.

The mol-ecule of the title compound, C(12)H(14)N(8)S(2), has an N-N gauche conformation. The triazine rings are nearly coplanar with respect to the imide bonds [C-C-C-N torsion angles = -15.3 (3) and -15.8 (3)°] and they are twisted by 77.88 (7)°. The overall conformation of the mol-ecule is stabilized by intra-molecular C-H⋯N hydrogen bonding. The mol-ecular packing is influenced by π-π inter-actions of the triazine systems with a shortest centroid-centroid separation of 3.5242 (12) Å.

Related literature

For the biological activity of hydrazones, see: Rollas et al. (2002 ▶); Terzioglu & Gürsoy (2003 ▶); Bedia et al. (2006 ▶). For the synthesis, see: Karczmarzyk et al. (2000 ▶); Rykowski et al. (2000 ▶); Mojzych & Rykowski (2003 ▶). For related structures, see: Lewis et al. (2000 ▶); Sauro & Workentin (2001 ▶); Tai et al. (2008 ▶).

Experimental

Crystal data

C12H14N8S2

M = 334.43

Monoclinic,

a = 14.4962 (4) Å

b = 7.0814 (2) Å

c = 15.6619 (5) Å

β = 107.465 (2)°

V = 1533.63 (8) Å3

Z = 4

Cu Kα radiation

μ = 3.24 mm−1

T = 293 K

0.32 × 0.22 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.474, T max = 0.753

5750 measured reflections

2635 independent reflections

2200 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.117

S = 1.03

2635 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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, 1997 ▶); software used to prepare material for publication: SHELXL97, WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025033/kp2223sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025033/kp2223Isup2.hkl

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

C12H14N8S2	F(000) = 696
Mr = 334.43	Dx = 1.448 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 1791 reflections
a = 14.4962 (4) Å	θ = 5.8–66.9°
b = 7.0814 (2) Å	µ = 3.24 mm−1
c = 15.6619 (5) Å	T = 293 K
β = 107.465 (2)°	Plate, yellow
V = 1533.63 (8) Å3	0.32 × 0.22 × 0.08 mm
Z = 4

Bruker APEXII CCD diffractometer	2635 independent reflections
Radiation source: fine-focus sealed tube	2200 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 67.7°, θmin = 5.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→17
Tmin = 0.474, Tmax = 0.753	k = −8→2
5750 measured reflections	l = −18→17

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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F2) = 0.117	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0575P)2 + 0.4463P] where P = (Fo2 + 2Fc2)/3
2635 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.22 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
S17	0.29719 (4)	0.25053 (8)	0.43807 (4)	0.0484 (2)
S21	0.94963 (5)	0.20147 (9)	0.04349 (4)	0.0524 (2)
N1	0.56957 (14)	0.2978 (3)	0.57615 (13)	0.0434 (4)
N2	0.47200 (14)	0.3040 (3)	0.55353 (12)	0.0416 (4)
N4	0.46056 (13)	0.1897 (2)	0.40671 (11)	0.0369 (4)
N8	0.69264 (14)	0.1583 (3)	0.38213 (12)	0.0430 (4)
N9	0.74256 (14)	0.0796 (3)	0.32936 (13)	0.0437 (5)
N11	0.92948 (16)	−0.1765 (3)	0.21425 (15)	0.0530 (5)
N12	0.95071 (15)	−0.0836 (3)	0.14810 (14)	0.0513 (5)
N14	0.86038 (13)	0.1842 (2)	0.17013 (12)	0.0391 (4)
C3	0.42339 (16)	0.2505 (3)	0.47130 (15)	0.0365 (5)
C5	0.55527 (16)	0.1885 (3)	0.42894 (14)	0.0346 (5)
C6	0.61047 (17)	0.2431 (3)	0.51602 (15)	0.0384 (5)
H61	0.6776	0.2403	0.5312	0.058*
C7	0.60199 (16)	0.1214 (3)	0.36205 (14)	0.0373 (5)
C10	0.77872 (16)	0.1880 (3)	0.28245 (14)	0.0399 (5)
C13	0.91659 (16)	0.0920 (3)	0.13019 (15)	0.0410 (5)
C15	0.83999 (15)	0.0913 (3)	0.23536 (14)	0.0374 (5)
C16	0.87630 (17)	−0.0913 (3)	0.25750 (16)	0.0476 (6)
H161	0.8624	−0.1544	0.3042	0.071*
C18	0.27045 (19)	0.3325 (3)	0.53668 (18)	0.0524 (6)
H181	0.2921	0.2408	0.5836	0.079*
H182	0.2019	0.3504	0.5235	0.079*
H183	0.3030	0.4502	0.5557	0.079*
C19	0.54418 (18)	0.0180 (3)	0.28090 (15)	0.0470 (6)
H191	0.5800	−0.0897	0.2712	0.071*
H192	0.5309	0.1002	0.2299	0.071*
H193	0.4844	−0.0232	0.2892	0.071*
C20	0.7638 (2)	0.3954 (3)	0.27192 (19)	0.0583 (7)
H201	0.8222	0.4541	0.2681	0.087*
H202	0.7476	0.4451	0.3226	0.087*
H203	0.7122	0.4211	0.2183	0.087*
C22	0.9029 (2)	0.4349 (4)	0.04713 (18)	0.0561 (6)
H221	0.8344	0.4284	0.0377	0.084*
H222	0.9156	0.5109	0.0011	0.084*
H223	0.9337	0.4904	0.1045	0.084*

	U11	U22	U33	U12	U13	U23
S17	0.0406 (3)	0.0580 (4)	0.0483 (4)	0.0010 (3)	0.0158 (3)	−0.0040 (3)
S21	0.0571 (4)	0.0614 (4)	0.0505 (4)	−0.0013 (3)	0.0341 (3)	−0.0052 (3)
N1	0.0458 (11)	0.0510 (10)	0.0343 (10)	−0.0001 (9)	0.0135 (8)	−0.0036 (8)
N2	0.0461 (11)	0.0460 (10)	0.0351 (10)	0.0023 (8)	0.0157 (8)	−0.0016 (8)
N4	0.0431 (10)	0.0387 (9)	0.0315 (9)	0.0004 (8)	0.0151 (8)	0.0010 (7)
N8	0.0475 (11)	0.0490 (10)	0.0386 (10)	−0.0007 (9)	0.0224 (9)	−0.0009 (8)
N9	0.0470 (11)	0.0506 (10)	0.0401 (10)	0.0022 (9)	0.0232 (9)	−0.0007 (8)
N11	0.0533 (12)	0.0532 (11)	0.0548 (12)	0.0129 (10)	0.0196 (10)	0.0027 (10)
N12	0.0525 (12)	0.0544 (11)	0.0522 (12)	0.0094 (9)	0.0237 (10)	−0.0023 (9)
N14	0.0382 (10)	0.0453 (10)	0.0372 (10)	−0.0016 (8)	0.0165 (8)	−0.0044 (8)
C3	0.0428 (12)	0.0319 (10)	0.0381 (12)	0.0010 (9)	0.0172 (10)	0.0033 (8)
C5	0.0435 (12)	0.0299 (9)	0.0340 (11)	−0.0010 (9)	0.0169 (9)	0.0039 (8)
C6	0.0389 (12)	0.0422 (11)	0.0357 (11)	−0.0008 (9)	0.0139 (9)	−0.0008 (9)
C7	0.0493 (13)	0.0349 (10)	0.0320 (11)	0.0016 (9)	0.0188 (9)	0.0052 (8)
C10	0.0391 (12)	0.0493 (12)	0.0337 (11)	0.0012 (9)	0.0143 (9)	−0.0020 (9)
C13	0.0375 (12)	0.0494 (12)	0.0392 (12)	−0.0022 (10)	0.0161 (9)	−0.0091 (9)
C15	0.0343 (11)	0.0458 (11)	0.0323 (11)	−0.0018 (9)	0.0105 (9)	−0.0030 (9)
C16	0.0470 (14)	0.0528 (13)	0.0440 (13)	0.0081 (10)	0.0154 (11)	0.0057 (10)
C18	0.0534 (15)	0.0535 (13)	0.0598 (16)	0.0080 (11)	0.0313 (13)	0.0023 (12)
C19	0.0565 (15)	0.0510 (13)	0.0373 (12)	−0.0026 (11)	0.0198 (11)	−0.0064 (10)
C20	0.0782 (19)	0.0466 (13)	0.0662 (17)	0.0049 (13)	0.0459 (15)	−0.0011 (12)
C22	0.0527 (15)	0.0635 (15)	0.0593 (16)	0.0019 (12)	0.0280 (13)	0.0089 (12)

S17—C3	1.745 (2)	C6—H61	0.9300
S17—C18	1.798 (2)	C7—C19	1.488 (3)
S21—C13	1.751 (2)	C10—C15	1.481 (3)
S21—C22	1.794 (3)	C10—C20	1.487 (3)
N1—C6	1.313 (3)	C15—C16	1.400 (3)
N1—N2	1.352 (3)	C16—H161	0.9300
N2—C3	1.324 (3)	C18—H181	0.9600
N4—C5	1.311 (3)	C18—H182	0.9600
N4—C3	1.352 (3)	C18—H183	0.9600
N8—C7	1.283 (3)	C19—H191	0.9600
N8—N9	1.370 (2)	C19—H192	0.9600
N9—C10	1.279 (3)	C19—H193	0.9600
N11—C16	1.315 (3)	C20—H201	0.9600
N11—N12	1.339 (3)	C20—H202	0.9600
N12—C13	1.337 (3)	C20—H203	0.9600
N14—C15	1.321 (3)	C22—H221	0.9600
N14—C13	1.337 (3)	C22—H222	0.9600
C5—C6	1.412 (3)	C22—H223	0.9600
C5—C7	1.486 (3)
C3—S17—C18	102.76 (12)	N14—C15—C10	117.49 (19)
C13—S21—C22	100.93 (11)	C16—C15—C10	122.7 (2)
C6—N1—N2	118.93 (19)	N11—C16—C15	122.1 (2)
C3—N2—N1	117.08 (18)	N11—C16—H161	119.0
C5—N4—C3	115.11 (18)	C15—C16—H161	119.0
C7—N8—N9	117.19 (19)	S17—C18—H181	109.5
C10—N9—N8	118.97 (18)	S17—C18—H182	109.5
C16—N11—N12	118.7 (2)	H181—C18—H182	109.5
C13—N12—N11	117.58 (19)	S17—C18—H183	109.5
C15—N14—C13	115.32 (19)	H181—C18—H183	109.5
N2—C3—N4	127.1 (2)	H182—C18—H183	109.5
N2—C3—S17	119.62 (17)	C7—C19—H191	109.5
N4—C3—S17	113.23 (17)	C7—C19—H192	109.5
N4—C5—C6	119.94 (19)	H191—C19—H192	109.5
N4—C5—C7	118.52 (19)	C7—C19—H193	109.5
C6—C5—C7	121.5 (2)	H191—C19—H193	109.5
N1—C6—C5	121.8 (2)	H192—C19—H193	109.5
N1—C6—H61	119.1	C10—C20—H201	109.5
C5—C6—H61	119.1	C10—C20—H202	109.5
N8—C7—C19	125.6 (2)	H201—C20—H202	109.5
N8—C7—C5	114.34 (19)	C10—C20—H203	109.5
C19—C7—C5	120.0 (2)	H201—C20—H203	109.5
N9—C10—C15	114.78 (19)	H202—C20—H203	109.5
N9—C10—C20	125.9 (2)	S21—C22—H221	109.5
C15—C10—C20	119.33 (19)	S21—C22—H222	109.5
N12—C13—N14	126.5 (2)	H221—C22—H222	109.5
N12—C13—S21	113.86 (16)	S21—C22—H223	109.5
N14—C13—S21	119.58 (17)	H221—C22—H223	109.5
N14—C15—C16	119.80 (19)	H222—C22—H223	109.5
C6—N1—N2—C3	1.1 (3)	C6—C5—C7—C19	163.73 (19)
C7—N8—N9—C10	114.8 (2)	N8—N9—C10—C15	173.76 (19)
C16—N11—N12—C13	0.3 (3)	N8—N9—C10—C20	−6.5 (4)
N1—N2—C3—N4	0.1 (3)	N11—N12—C13—N14	−2.1 (4)
N1—N2—C3—S17	178.80 (15)	N11—N12—C13—S21	179.33 (17)
C5—N4—C3—N2	−1.6 (3)	C15—N14—C13—N12	2.1 (3)
C5—N4—C3—S17	179.68 (14)	C15—N14—C13—S21	−179.36 (16)
C18—S17—C3—N2	0.15 (19)	C22—S21—C13—N12	−174.30 (19)
C18—S17—C3—N4	179.03 (15)	C22—S21—C13—N14	7.0 (2)
C3—N4—C5—C6	1.8 (3)	C13—N14—C15—C16	−0.5 (3)
C3—N4—C5—C7	179.32 (16)	C13—N14—C15—C10	179.41 (19)
N2—N1—C6—C5	−0.8 (3)	N9—C10—C15—N14	164.3 (2)
N4—C5—C6—N1	−0.7 (3)	C20—C10—C15—N14	−15.4 (3)
C7—C5—C6—N1	−178.20 (18)	N9—C10—C15—C16	−15.8 (3)
N9—N8—C7—C19	−7.1 (3)	C20—C10—C15—C16	164.4 (2)
N9—N8—C7—C5	171.86 (17)	N12—N11—C16—C15	1.2 (4)
N4—C5—C7—N8	167.24 (18)	N14—C15—C16—N11	−1.1 (4)
C6—C5—C7—N8	−15.3 (3)	C10—C15—C16—N11	179.0 (2)
N4—C5—C7—C19	−13.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H193···N4	0.96	2.48	2.875 (3)	104
C20—H202···N8	0.96	2.46	2.816 (3)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H193⋯N4	0.96	2.48	2.875 (3)	104
C20—H202⋯N8	0.96	2.46	2.816 (3)	101