![](/logos/buttonlogos/cross.png)
![](/logos/buttonlogos/cross.png)
organic compounds
1,3-Dithian-2-one azine
aCollege of Life Science and Chemistry, Tianshui Normal University, Tianshui 741000, People's Republic of China, and bCollege of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, 225002, People's Republic of China
*Correspondence e-mail: yhliuyzu@yahoo.com.cn
In an 8H12N2S4, there are two crystallographically independent half molecules lying on inversion centers. One of the molecules is disordered over two positions with relative occupancies of 82.0 (2) and 18.0 (2) for the major and minor components. In the molecules are linked into a three-dimensional framework via intermolecular C—H⋯N hydrogen-bonding interactions.
of the title compound, CRelated 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
|
Refinement
|
|
Data collection: SMART (Bruker, 2002); cell 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
).
Supporting information
10.1107/S1600536810010524/pv2263sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536810010524/pv2263Isup2.hkl
The title compound was prepared according to the reference method (Mayer & Schaefer, 1964; Xu et al., 2005) and crystallized from a mixture of ethanol and petroleum ether (1:8).
The atoms of the molecule B are disordered over two positions with relative occupancies of 82.0 (2) and 18.0 (2) for the major and minor components, respectively; their anisotropic dispalcement parameters were constrained to be equal. Restraints were applied to bond distances in the disordered molecule B in reference to the molecule A. All H atoms were placed at ideal positions and allowed to ride on the parent C atoms, with C–H = 0.97 and Uiso(H) values of 1.2Ueq(C).
Data collection: SMART (Bruker, 2002); cell
SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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).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 monochromator | 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 |
C8H12N2S4 | V = 1203.4 (2) Å3 |
Mr = 264.44 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.3999 (11) Å | µ = 0.75 mm−1 |
b = 11.9251 (14) Å | T = 293 K |
c = 10.7397 (13) Å | 0.22 × 0.21 × 0.19 mm |
β = 91.555 (2)° |
Bruker SMART 1000 CCD diffractometer | 2998 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 2478 reflections with I > 2σ(I) |
Tmin = 0.852, Tmax = 0.870 | Rint = 0.055 |
10905 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 14 restraints |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.65 e Å−3 |
2998 reflections | Δρmin = −0.41 e Å−3 |
151 parameters |
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 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, −y, −z. |
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 |
Symmetry codes: (i) −x+1, −y+1, −z; (iii) x, −y+1/2, z+1/2; (iv) −x+1, y−1/2, −z+1/2; (v) −x+2, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C8H12N2S4 |
Mr | 264.44 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 9.3999 (11), 11.9251 (14), 10.7397 (13) |
β (°) | 91.555 (2) |
V (Å3) | 1203.4 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.75 |
Crystal size (mm) | 0.22 × 0.21 × 0.19 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.852, 0.870 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10905, 2998, 2478 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.669 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.127, 1.01 |
No. of reflections | 2998 |
No. of parameters | 151 |
No. of restraints | 14 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.65, −0.41 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).
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) x, −y+1/2, z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+2, −y+1, −z; (iv) −x+1, −y+1, −z. |
Acknowledgements
The authors thank the Natural Science Foundation of Tianshui Normal College (No. TSA 0602) and Yangzhou University (No. 2006XJJ03) for financial support of this work.
References
Beghidja, C., Rogez, G., Kortus, J., Wesolek, M. & Welter, R. (2006). J. Am. Chem. Soc. 128, 3140–3141. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Boeyens, J. C. A. (1978). J. Cryst. Mol. Struct. 8, 317–320. CrossRef Web of Science Google Scholar
Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dong, D., Ouyang, Y., Yu, H., Liu, Q., Liu, J., Wang, M. & Zhu, J. (2005). J. Org. Chem. 70, 4535–4537. Web of Science CrossRef PubMed CAS Google Scholar
Gou, S.-H., Chen, H.-C., Fang, Z.-P., Luo, J. & Wang, Y.-L. (2004). Chin. J. Org. Chem. 24, 234–238. CAS Google Scholar
Liu, Y.-H., Liu, X.-L., Dai, X.-Q., Xu, W. & Guo, R. (2008). J. Chem. Crystallogr. 38, 109–113. Web of Science CSD CrossRef CAS Google Scholar
Liu, J.-F., Liu, X.-L. & Liu, Y.-H. (2008). Acta Cryst. E64, o1340. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mayer, R. & Schaefer, K. (1964). J. Prakt. Chem. 26, 279–295. CrossRef CAS Web of Science Google Scholar
Ram, V. J., Nath, M. & ShuklaP, K. (1997). Bioorg. Med. Chem. Lett. 7, 2137–2140. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, L. Z., Xu, H. Z., Yang, S. H., Li, C. L. & Zhou, K. (2005). Acta Cryst. E61, o31–o32. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yang, L.-J., Li, Z.-G., Liu, X.-L. & Liu, Y.-H. (2007). Acta Cryst. E63, o4501. Web of Science CSD CrossRef IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The derivatives of 2-hydrazono-1,3-dithiolane have been abstracted for their coordination chemistry and biological activities (Beghidja et al., 2006; Gou et al., 2004). The derivatives of 1,3-dithian-2-ylidene and thiazolidin-2-ylidene are a novel class of antimycotic agents and important synthesis mediam (Ram et al., 1997; Dong et al., 2005). But very few derivatives of 2-hydrazono-1,3-dithiane have been reported. As on going research in this field in our laboratory (Liu et al., 2008; Yang et al., 2007), we report herein the structure of the title compound.
In the title compound, there are two crystallographically independent half molecules in the asymmetric unit, which lie on centres of symmetry; referred as molecules A and B. The atoms of the molecule B are disordered over two positions with relative occupancies of 82.0 (2) and 18.0 (2) for the major and minor components, respectively. All the dithian rings adopt twist-boat conformations (Boeyens, 1978). The atoms S1/S2/C1/C3/N1 in molecule A lie in a plane and the atoms C2 and C4 lie above and below this plane. Similarly, atoms S3/S4/C5/C7/N2 in molecule B also lie in a plane and the atoms C6 and C8 lie above and below the plane. The molecular dimensions in the two molecules are similar with the corresponding molecular dimensions reported in similar structures from our previous work (Yang et al.., 2007; Liu, Liu & Liu, (2008); Liu, Liu, Dai et al., (2008).
In the crystal structure the molecules are joined into a zig-zag chain by C8–H8B···N1 inter-molecular hydrogen-bond (Fig. 2, Tab. 1). At the same time C2–H2B···N2 inter-molecular hydrogen-bonds form another zig-zag chain along the molecular long axis and vertically the first chain. Both of them generate a sheet with edge-fused R44(22) rings in graph set notation (Bernstein et al., 1995) in the ab-plane. Besides these chains, there are two more zig-zag chains, formed by C6–H6B···N1 and C4–H4B···N2 inter-molecular hydrogen-bonds which make up the adjacent sheet into a three dimensional frame work along the c axis (Fig. 3).