1,3-Dithian-2-one azine.

In an asymmetric unit of the title compound, C(8)H(12)N(2)S(4), there are two crystallographically independent half mol-ecules lying on inversion centers. One of the mol-ecules is disordered over two positions with relative occupancies of 82.0 (2) and 18.0 (2) for the major and minor components. In the crystal structure, mol-ecules are linked into a three-dimensional framework via inter-molecular C-H⋯N hydrogen-bonding inter-actions.

Related literature

For the synthesis, see: Mayer & Schaefer (1964 ▶); Xu et al. (2005 ▶). For the use of 2-hydrazono-1,3-dithiol­ane derivatives in coordination chemistry and their biological activity, see: Beghidja et al. (2006 ▶); Gou et al. (2004 ▶). For 1,3-dithian-2-yl­idene derivatives as anti­mycotic agents and an important synthesis medium, see: Dong et al. (2005 ▶); Ram et al. (1997 ▶). For related structures, see: Liu, Liu & Liu (2008 ▶); Liu, Liu, Dai et al. (2008 ▶); Yang et al. (2007 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For dithian ring conformations, see: Boeyens (1978 ▶).

Experimental

Crystal data

C8H12N2S4

M = 264.44

Monoclinic,

a = 9.3999 (11) Å

b = 11.9251 (14) Å

c = 10.7397 (13) Å

β = 91.555 (2)°

V = 1203.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.75 mm−1

T = 293 K

0.22 × 0.21 × 0.19 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.852, T max = 0.870

10905 measured reflections

2998 independent reflections

2478 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.127

S = 1.01

2998 reflections

151 parameters

14 restraints

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.41 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810010524/pv2263sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010524/pv2263Isup2.hkl

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

C8H12N2S4	F(000) = 552
Mr = 264.44	Dx = 1.460 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5734 reflections
a = 9.3999 (11) Å	θ = 2.8–28.2°
b = 11.9251 (14) Å	µ = 0.75 mm−1
c = 10.7397 (13) Å	T = 293 K
β = 91.555 (2)°	Block, colorless
V = 1203.4 (2) Å3	0.22 × 0.21 × 0.19 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	2998 independent reflections
Radiation source: fine-focus sealed tube	2478 reflections with I > 2σ(I)
graphite	Rint = 0.055
φ & ω scans	θmax = 28.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −12→12
Tmin = 0.852, Tmax = 0.870	k = −15→15
10905 measured reflections	l = −14→14

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0561P)2 + 0.7487P] where P = (Fo2 + 2Fc2)/3
2998 reflections	(Δ/σ)max < 0.001
151 parameters	Δρmax = 0.65 e Å−3
14 restraints	Δρmin = −0.41 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 > 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	0.71338 (9)	0.70901 (9)	−0.02533 (9)	0.0596 (3)	0.820 (2)
S2	0.74955 (10)	0.49843 (7)	0.12799 (9)	0.0510 (2)	0.820 (2)
N1	0.5250 (2)	0.5510 (2)	−0.0239 (2)	0.0424 (5)	0.820 (2)
C1	0.6487 (3)	0.5788 (2)	0.0219 (2)	0.0373 (5)	0.820 (2)
C2	0.9037 (4)	0.6810 (11)	−0.0147 (11)	0.0581 (12)	0.820 (2)
H2A	0.9235	0.6125	−0.0598	0.070*	0.820 (2)
H2B	0.9540	0.7416	−0.0545	0.070*	0.820 (2)
C3	0.9597 (16)	0.6690 (9)	0.1184 (11)	0.0525 (15)	0.820 (2)
H3A	1.0489	0.6282	0.1185	0.063*	0.820 (2)
H3B	0.9787	0.7430	0.1525	0.063*	0.820 (2)
C4	0.8569 (18)	0.6085 (10)	0.2011 (13)	0.0554 (15)	0.820 (2)
H4A	0.7930	0.6637	0.2355	0.053 (9)*	0.820 (2)
H4B	0.9109	0.5758	0.2702	0.072 (12)*	0.820 (2)
S1'	0.6929 (5)	0.6622 (4)	−0.0158 (5)	0.0596 (3)	0.180 (2)
S2'	0.7925 (5)	0.4809 (4)	0.1612 (5)	0.0510 (2)	0.180 (2)
N1'	0.5477 (10)	0.4742 (9)	0.0420 (10)	0.0424 (5)	0.180 (2)
C1'	0.6632 (10)	0.5345 (8)	0.0577 (10)	0.0373 (5)	0.180 (2)
C2'	0.8826 (16)	0.687 (5)	−0.007 (6)	0.0581 (12)	0.180 (2)
H2C	0.9253	0.6486	−0.0756	0.070*	0.180 (2)
H2D	0.8981	0.7670	−0.0190	0.070*	0.180 (2)
C3'	0.962 (8)	0.653 (5)	0.112 (5)	0.0525 (15)	0.180 (2)
H3D	1.0285	0.5940	0.0920	0.063*	0.180 (2)
H3C	1.0171	0.7168	0.1423	0.063*	0.180 (2)
C4'	0.868 (9)	0.613 (4)	0.215 (7)	0.0554 (15)	0.180 (2)
H4D	0.7935	0.6667	0.2298	0.066*	0.180 (2)
H4C	0.9236	0.6018	0.2911	0.066*	0.180 (2)
S3	0.72455 (7)	0.16120 (6)	−0.00561 (6)	0.0599 (2)
S4	0.79852 (6)	−0.03342 (5)	0.16643 (6)	0.04884 (18)
N2	0.9581 (2)	0.04587 (17)	−0.02005 (18)	0.0489 (5)
C5	0.8418 (2)	0.05424 (19)	0.0413 (2)	0.0428 (5)
C6	0.6094 (2)	−0.0073 (2)	0.1744 (2)	0.0541 (6)
H6A	0.5649	−0.0259	0.0945	0.065*
H6B	0.5702	−0.0570	0.2362	0.065*
C7	0.5708 (4)	0.1115 (3)	0.2068 (4)	0.0831 (11)
H7A	0.5798	0.1205	0.2965	0.100*
H7B	0.4717	0.1239	0.1831	0.100*
C8	0.6605 (3)	0.2012 (2)	0.1454 (3)	0.0649 (7)
H8A	0.7415	0.2185	0.1999	0.078*
H8B	0.6041	0.2690	0.1361	0.078*

	U11	U22	U33	U12	U13	U23
S1	0.0474 (4)	0.0466 (6)	0.0836 (5)	−0.0132 (4)	−0.0182 (4)	0.0194 (4)
S2	0.0423 (5)	0.0480 (4)	0.0625 (5)	−0.0055 (3)	−0.0045 (3)	0.0150 (3)
N1	0.0389 (12)	0.0444 (12)	0.0440 (11)	−0.0099 (10)	0.0005 (9)	0.0025 (9)
C1	0.0360 (11)	0.0375 (14)	0.0385 (13)	−0.0038 (11)	0.0038 (9)	−0.0002 (9)
C2	0.0420 (16)	0.069 (2)	0.063 (2)	−0.015 (3)	0.002 (2)	0.0097 (18)
C3	0.0398 (14)	0.048 (4)	0.069 (2)	−0.008 (3)	−0.0076 (15)	0.002 (2)
C4	0.044 (3)	0.0705 (19)	0.051 (4)	−0.0066 (13)	−0.006 (3)	−0.0005 (16)
S1'	0.0474 (4)	0.0466 (6)	0.0836 (5)	−0.0132 (4)	−0.0182 (4)	0.0194 (4)
S2'	0.0423 (5)	0.0480 (4)	0.0625 (5)	−0.0055 (3)	−0.0045 (3)	0.0150 (3)
N1'	0.0389 (12)	0.0444 (12)	0.0440 (11)	−0.0099 (10)	0.0005 (9)	0.0025 (9)
C1'	0.0360 (11)	0.0375 (14)	0.0385 (13)	−0.0038 (11)	0.0038 (9)	−0.0002 (9)
C2'	0.0420 (16)	0.069 (2)	0.063 (2)	−0.015 (3)	0.002 (2)	0.0097 (18)
C3'	0.0398 (14)	0.048 (4)	0.069 (2)	−0.008 (3)	−0.0076 (15)	0.002 (2)
C4'	0.044 (3)	0.0705 (19)	0.051 (4)	−0.0066 (13)	−0.006 (3)	−0.0005 (16)
S3	0.0493 (4)	0.0688 (5)	0.0621 (4)	0.0031 (3)	0.0130 (3)	0.0238 (3)
S4	0.0423 (3)	0.0489 (3)	0.0557 (3)	−0.0007 (2)	0.0075 (2)	0.0089 (2)
N2	0.0451 (10)	0.0511 (11)	0.0511 (10)	−0.0027 (8)	0.0109 (8)	0.0014 (8)
C5	0.0382 (10)	0.0455 (11)	0.0449 (11)	−0.0057 (9)	0.0069 (8)	−0.0018 (9)
C6	0.0391 (11)	0.0677 (16)	0.0560 (13)	−0.0061 (11)	0.0097 (10)	0.0143 (11)
C7	0.0716 (19)	0.080 (2)	0.100 (2)	0.0246 (17)	0.0506 (18)	0.0327 (18)
C8	0.0587 (15)	0.0575 (15)	0.0798 (18)	0.0140 (13)	0.0237 (13)	0.0095 (13)

S1—C1	1.748 (3)	C2'—H2C	0.9700
S1—C2	1.821 (5)	C2'—H2D	0.9700
S2—C1	1.749 (3)	C3'—C4'	1.512 (10)
S2—C4	1.821 (4)	C3'—H3D	0.9700
N1—C1	1.293 (3)	C3'—H3C	0.9700
N1—N1i	1.406 (4)	C4'—H4D	0.9700
C2—C3	1.516 (5)	C4'—H4C	0.9700
C2—H2A	0.9700	S3—C5	1.751 (2)
C2—H2B	0.9700	S3—C8	1.810 (3)
C3—C4	1.514 (5)	S4—C5	1.759 (2)
C3—H3A	0.9700	S4—C6	1.809 (2)
C3—H3B	0.9700	N2—C5	1.296 (3)
C4—H4A	0.9700	N2—N2ii	1.409 (4)
C4—H4B	0.9700	C6—C7	1.505 (4)
S1'—C1'	1.741 (8)	C6—H6A	0.9700
S1'—C2'	1.809 (10)	C6—H6B	0.9700
S2'—C1'	1.746 (8)	C7—C8	1.523 (4)
S2'—C4'	1.811 (10)	C7—H7A	0.9700
N1'—C1'	1.309 (9)	C7—H7B	0.9700
N1'—N1'i	1.40 (2)	C8—H8A	0.9700
C2'—C3'	1.513 (10)	C8—H8B	0.9700
C1—S1—C2	99.6 (4)	C4'—C3'—C2'	115 (6)
C1—S2—C4	99.8 (6)	C4'—C3'—H3D	108.6
C1—N1—N1i	112.9 (3)	C2'—C3'—H3D	108.6
N1—C1—S1	115.7 (2)	C4'—C3'—H3C	108.6
N1—C1—S2	125.0 (2)	C2'—C3'—H3C	108.6
S1—C1—S2	119.30 (14)	H3D—C3'—H3C	107.6
C3—C2—S1	113.1 (9)	C3'—C4'—S2'	106 (4)
C3—C2—H2A	109.0	C3'—C4'—H4D	110.5
S1—C2—H2A	109.0	S2'—C4'—H4D	110.5
C3—C2—H2B	109.0	C3'—C4'—H4C	110.5
S1—C2—H2B	109.0	S2'—C4'—H4C	110.5
H2A—C2—H2B	107.8	H4D—C4'—H4C	108.7
C4—C3—C2	112.8 (12)	C5—S3—C8	99.00 (12)
C4—C3—H3A	109.0	C5—S4—C6	100.47 (11)
C2—C3—H3A	109.0	C5—N2—N2ii	112.1 (2)
C4—C3—H3B	109.0	N2—C5—S3	116.29 (17)
C2—C3—H3B	109.0	N2—C5—S4	123.96 (19)
H3A—C3—H3B	107.8	S3—C5—S4	119.75 (12)
C3—C4—S2	116.5 (8)	C7—C6—S4	114.6 (2)
C3—C4—H4A	108.2	C7—C6—H6A	108.6
S2—C4—H4A	108.2	S4—C6—H6A	108.6
C3—C4—H4B	108.2	C7—C6—H6B	108.6
S2—C4—H4B	108.2	S4—C6—H6B	108.6
H4A—C4—H4B	107.3	H6A—C6—H6B	107.6
C1'—S1'—C2'	107 (2)	C6—C7—C8	114.9 (2)
C1'—S2'—C4'	98 (3)	C6—C7—H7A	108.5
C1'—N1'—N1'i	111.0 (11)	C8—C7—H7A	108.5
N1'—C1'—S1'	124.3 (7)	C6—C7—H7B	108.5
N1'—C1'—S2'	116.2 (7)	C8—C7—H7B	108.5
S1'—C1'—S2'	119.4 (5)	H7A—C7—H7B	107.5
C3'—C2'—S1'	118 (4)	C7—C8—S3	113.8 (2)
C3'—C2'—H2C	107.9	C7—C8—H8A	108.8
S1'—C2'—H2C	107.9	S3—C8—H8A	108.8
C3'—C2'—H2D	107.9	C7—C8—H8B	108.8
S1'—C2'—H2D	107.9	S3—C8—H8B	108.8
H2C—C2'—H2D	107.2	H8A—C8—H8B	107.7

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···N2iii	0.97	2.71	3.620 (7)	157
C4'—H4C···N2iii	0.97	2.70	3.503 (7)	141
C6—H6B···N1iii	0.97	2.62	3.397 (6)	137
C6—H6B···N1'iv	0.97	2.68	3.428 (6)	134
C2'—H2D···N2v	0.97	2.64	3.529 (7)	152
C2—H2B···N2v	0.97	2.78	3.523 (7)	134
C8—H8B···N1i	0.97	2.73	3.654 (3)	159
C8—H8B···N1'	0.97	2.70	3.591 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4B⋯N2i	0.97	2.71	3.620 (7)	157
C4′—H4C⋯N2i	0.97	2.70	3.503 (7)	141
C6—H6B⋯N1i	0.97	2.62	3.397 (6)	137
C6—H6B⋯N1′ii	0.97	2.68	3.428 (6)	134
C2′—H2D⋯N2iii	0.97	2.64	3.529 (7)	152
C2—H2B⋯N2iii	0.97	2.78	3.523 (7)	134
C8—H8B⋯N1iv	0.97	2.73	3.654 (3)	159
C8—H8B⋯N1′	0.97	2.70	3.591 (3)	154

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