1-[2-(Pyrazin-2-ylsulfan-yl)eth-yl]pyrazine-2(1H)-thione.

The title multifunctional twisted organic ligand, C(10)H(10)N(4)S(2), contains a short C=S bond [1.671 (2) Å]. The dihedral angle between the two pyrazine rings is 39.83 (6)°. In the crystal, inter-molecular C-H⋯N and C-H⋯S hydrogen bonds result in the formation of a supra-molecular network.

Related literature

The assembly of mol­ecular units in predefined arrangements is a key goal in the synthesis of crystal structures by design, see: Zheng et al. (2003 ▶). For bond lengths and angles in the ligand, see: Etter et al. (1992 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For versatile ligands, see: Devel et al. (2003 ▶).

Experimental

Crystal data

C10H10N4S2

M = 250.34

Monoclinic,

a = 9.762 (7) Å

b = 11.737 (9) Å

c = 10.129 (8) Å

β = 92.628 (9)°

V = 1159.2 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.44 mm−1

T = 296 K

0.32 × 0.20 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.873, T max = 0.966

6280 measured reflections

2160 independent reflections

1879 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.085

S = 1.06

2160 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.22 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 datablocks I, global. DOI: 10.1107/S1600536811001474/bv2167sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001474/bv2167Isup2.hkl

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

C10H10N4S2	F(000) = 520
Mr = 250.34	Dx = 1.434 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.762 (7) Å	Cell parameters from 3231 reflections
b = 11.737 (9) Å	θ = 2.7–27.9°
c = 10.129 (8) Å	µ = 0.44 mm−1
β = 92.628 (9)°	T = 296 K
V = 1159.2 (15) Å3	Block, yellow
Z = 4	0.32 × 0.20 × 0.08 mm

Bruker SMART CCD area-detector diffractometer	2160 independent reflections
Radiation source: fine-focus sealed tube	1879 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 25.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −11→11
Tmin = 0.873, Tmax = 0.966	k = −14→12
6280 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.039P)2 + 0.347P] where P = (Fo2 + 2Fc2)/3
2160 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.22 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
C1	0.86032 (16)	0.00044 (13)	0.30816 (17)	0.0373 (4)
C2	0.83823 (17)	−0.05822 (14)	0.42873 (18)	0.0418 (4)
H2	0.8326	−0.1372	0.4242	0.050*
C3	0.83014 (18)	0.10299 (16)	0.54879 (19)	0.0464 (4)
H3	0.8205	0.1393	0.6295	0.056*
C4	0.84852 (16)	0.16689 (14)	0.44097 (18)	0.0413 (4)
H4	0.8502	0.2459	0.4481	0.050*
C5	0.8960 (2)	0.18947 (15)	0.20807 (19)	0.0460 (4)
H5A	0.8572	0.2646	0.2203	0.055*
H5B	0.8538	0.1572	0.1280	0.055*
C6	1.0492 (2)	0.20010 (15)	0.19297 (18)	0.0479 (4)
H6A	1.0649	0.2399	0.1111	0.058*
H6B	1.0879	0.1243	0.1861	0.058*
C7	1.08904 (17)	0.41615 (14)	0.29421 (17)	0.0373 (4)
C8	1.1302 (2)	0.49827 (17)	0.3863 (2)	0.0593 (5)
H8	1.1800	0.4757	0.4623	0.071*
C9	1.0294 (2)	0.63363 (17)	0.2595 (2)	0.0587 (5)
H9	1.0053	0.7093	0.2443	0.070*
C10	0.99020 (19)	0.55385 (15)	0.1681 (2)	0.0494 (5)
H10	0.9419	0.5771	0.0915	0.059*
N1	0.86480 (13)	0.11696 (11)	0.32118 (14)	0.0366 (3)
N2	0.82515 (15)	−0.01237 (13)	0.54431 (15)	0.0464 (4)
N3	1.01858 (15)	0.44304 (12)	0.18458 (15)	0.0435 (4)
N4	1.1012 (2)	0.60692 (15)	0.3698 (2)	0.0706 (5)
S2	1.13825 (5)	0.27417 (4)	0.32673 (5)	0.04440 (15)
S1	0.87993 (6)	−0.06784 (4)	0.16546 (5)	0.05616 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0380 (9)	0.0282 (8)	0.0447 (9)	−0.0010 (6)	−0.0081 (7)	−0.0002 (7)
C2	0.0419 (9)	0.0322 (9)	0.0504 (11)	−0.0052 (7)	−0.0058 (8)	0.0033 (7)
C3	0.0401 (9)	0.0512 (11)	0.0483 (10)	−0.0018 (8)	0.0067 (8)	−0.0111 (9)
C4	0.0360 (9)	0.0328 (9)	0.0549 (11)	0.0003 (7)	0.0008 (8)	−0.0097 (8)
C5	0.0614 (11)	0.0279 (9)	0.0477 (10)	−0.0020 (8)	−0.0083 (9)	0.0071 (7)
C6	0.0671 (12)	0.0311 (9)	0.0463 (10)	−0.0027 (8)	0.0097 (9)	0.0012 (7)
C7	0.0380 (9)	0.0327 (8)	0.0415 (9)	−0.0037 (7)	0.0035 (7)	0.0037 (7)
C8	0.0782 (14)	0.0452 (11)	0.0527 (12)	−0.0052 (10)	−0.0172 (10)	−0.0010 (9)
C9	0.0630 (12)	0.0311 (10)	0.0815 (15)	0.0021 (8)	−0.0012 (11)	0.0003 (10)
C10	0.0481 (10)	0.0384 (10)	0.0610 (12)	0.0015 (8)	−0.0052 (9)	0.0091 (8)
N1	0.0382 (7)	0.0266 (7)	0.0445 (8)	0.0006 (5)	−0.0043 (6)	0.0001 (6)
N2	0.0426 (8)	0.0493 (9)	0.0473 (9)	−0.0054 (7)	0.0015 (7)	0.0029 (7)
N3	0.0496 (9)	0.0339 (8)	0.0464 (9)	−0.0016 (6)	−0.0042 (7)	0.0035 (6)
N4	0.0953 (14)	0.0412 (10)	0.0735 (13)	−0.0043 (9)	−0.0152 (11)	−0.0117 (9)
S2	0.0490 (3)	0.0346 (3)	0.0494 (3)	−0.00021 (18)	0.0004 (2)	0.01038 (18)
S1	0.0878 (4)	0.0359 (3)	0.0439 (3)	0.0014 (2)	−0.0074 (3)	−0.00664 (19)

C1—N1	1.374 (2)	C6—S2	1.800 (2)
C1—C2	1.427 (3)	C6—H6A	0.9700
C1—S1	1.671 (2)	C6—H6B	0.9700
C2—N2	1.300 (2)	C7—N3	1.317 (2)
C2—H2	0.9300	C7—C8	1.388 (3)
C3—C4	1.344 (3)	C7—S2	1.761 (2)
C3—N2	1.356 (3)	C8—N4	1.315 (3)
C3—H3	0.9300	C8—H8	0.9300
C4—N1	1.363 (2)	C9—N4	1.328 (3)
C4—H4	0.9300	C9—C10	1.359 (3)
C5—N1	1.470 (2)	C9—H9	0.9300
C5—C6	1.515 (3)	C10—N3	1.339 (2)
C5—H5A	0.9700	C10—H10	0.9300
C5—H5B	0.9700
N1—C1—C2	113.79 (15)	S2—C6—H6B	108.7
N1—C1—S1	123.76 (13)	H6A—C6—H6B	107.6
C2—C1—S1	122.45 (14)	N3—C7—C8	121.60 (17)
N2—C2—C1	126.58 (17)	N3—C7—S2	120.77 (13)
N2—C2—H2	116.7	C8—C7—S2	117.60 (15)
C1—C2—H2	116.7	N4—C8—C7	122.3 (2)
C4—C3—N2	122.43 (17)	N4—C8—H8	118.9
C4—C3—H3	118.8	C7—C8—H8	118.9
N2—C3—H3	118.8	N4—C9—C10	122.09 (19)
C3—C4—N1	120.59 (16)	N4—C9—H9	119.0
C3—C4—H4	119.7	C10—C9—H9	119.0
N1—C4—H4	119.7	N3—C10—C9	122.29 (19)
N1—C5—C6	111.51 (15)	N3—C10—H10	118.9
N1—C5—H5A	109.3	C9—C10—H10	118.9
C6—C5—H5A	109.3	C4—N1—C1	120.57 (14)
N1—C5—H5B	109.3	C4—N1—C5	118.78 (15)
C6—C5—H5B	109.3	C1—N1—C5	120.53 (14)
H5A—C5—H5B	108.0	C2—N2—C3	116.02 (16)
C5—C6—S2	114.12 (13)	C7—N3—C10	115.77 (16)
C5—C6—H6A	108.7	C8—N4—C9	115.98 (18)
S2—C6—H6A	108.7	C7—S2—C6	101.42 (9)
C5—C6—H6B	108.7
N1—C1—C2—N2	−1.3 (3)	C6—C5—N1—C4	92.37 (18)
S1—C1—C2—N2	178.29 (14)	C6—C5—N1—C1	−83.77 (19)
N2—C3—C4—N1	−0.8 (3)	C1—C2—N2—C3	1.6 (3)
N1—C5—C6—S2	−65.89 (18)	C4—C3—N2—C2	−0.5 (3)
N3—C7—C8—N4	0.2 (3)	C8—C7—N3—C10	0.2 (3)
S2—C7—C8—N4	178.53 (18)	S2—C7—N3—C10	−178.07 (13)
N4—C9—C10—N3	1.5 (3)	C9—C10—N3—C7	−1.0 (3)
C3—C4—N1—C1	1.1 (2)	C7—C8—N4—C9	0.2 (3)
C3—C4—N1—C5	−175.01 (16)	C10—C9—N4—C8	−1.0 (3)
C2—C1—N1—C4	−0.2 (2)	N3—C7—S2—C6	−7.14 (16)
S1—C1—N1—C4	−179.72 (12)	C8—C7—S2—C6	174.49 (16)
C2—C1—N1—C5	175.90 (15)	C5—C6—S2—C7	−74.03 (14)
S1—C1—N1—C5	−3.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N4i	0.93	2.56	3.298 (3)	137
C2—H2···S2ii	0.93	2.99	3.544 (3)	119
C3—H3···S2iii	0.93	2.92	3.741 (3)	148
C8—H8···S1iv	0.93	2.97	3.738 (3)	140
C9—H9···S1v	0.93	2.98	3.897 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N4i	0.93	2.56	3.298 (3)	137
C2—H2⋯S2ii	0.93	2.99	3.544 (3)	119
C3—H3⋯S2iii	0.93	2.92	3.741 (3)	148
C8—H8⋯S1iv	0.93	2.97	3.738 (3)	140
C9—H9⋯S1v	0.93	2.98	3.897 (3)	169

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