Bis(1,2,3,4-tetra­hydro­quinoline-1-thio­carbon­yl) disulfide

Srinivasan, N.; Thirumaran, S.; Selvanayagam, S.

doi:10.1107/S1600536812047320

Volume 68
Part 12
Page o3446
December 2012

Received 21 October 2012
Accepted 17 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.003 Å
R = 0.038
wR = 0.104
Data-to-parameter ratio = 21.0
Details

Bis(1,2,3,4-tetrahydroquinoline-1-thiocarbonyl) disulfide

N. Srinivasan,^a S. Thirumaran ^a and S. Selvanayagam ^b ^*

^aDepartment of Chemistry, Annamalai University, Annamalainagar 608 002, India, and ^bDepartment of Physics, Kalasalingam University, Krishnankoil 626 126, India
Correspondence e-mail: s_selvanayagam@rediffmail.com

In the title compound, C₂₀H₂₀N₂S₄, the N-containing six-membered rings of the two tetrahydroquinoline moieties adopt half-chair conformations. Intramolecular C-HS hydrogen bonding stabilizes the molecular structure. In the crystal, molecules associate via weak C-H [pi] interactions.

Related literature

For general background to the title compound, see: Von Deuten et al. (1980); Kumar et al. (1990); Fun et al. (2001). For preparation of the title compound, see: Garg et al. (1993). For related structures, see: Ivanov et al. (2003); Jian et al. (1999); Fun et al. (2001). For ring-puckering parameters, see: Nardelli (1983).

Experimental

Crystal data

C₂₀H₂₀N₂S₄
M_r = 416.62
Monoclinic, P 2₁ /c
a = 8.1019 (4) Å
b = 20.3208 (11) Å
c = 12.3647 (6) Å
= 104.371 (2)°
V = 1971.99 (17) Å³
Z = 4
Mo K radiation
= 0.49 mm^-1
T = 292 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.867, T_max = 0.909
44844 measured reflections
4941 independent reflections
4036 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.104
S = 1.03
4941 reflections
235 parameters
H-atom parameters constrained
_max = 0.53 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4-C9 phenyl ring.

D-HA	D-H	HA	DA	D-HA
C12-H12BS4	0.97	2.53	3.028 (2)	112
C18-H18Cg1ⁱ		2.74	3.604 (2)	154
Symmetry code: (i) -x, -y, -z+2.

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2; data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2186 ).

Acknowledgements

The authors thank the SAIF, Indian Institute of Technology, Chennai, for the data collection.

References

Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Fun, H.-K., Chantrapromma, S., Razak, I. A., Bei, F.-L., Jian, F.-F., Yang, X.-J., Lu, L. & Wang, X. (2001). Acta Cryst. E57, o717-o718.
Garg, B. S., Garg, R. K. & Reddy, M. J. (1993). Indian J. Chem. Sect. A, 32, 697-700.
Ivanov, A. V., Larionov, S. A., Forsling, W., Antzutkin, O. N. & Kritikos, M. (2003). Russ. J. Coord. Chem. 29, 142-150
Jian, F., Jiang, L., Fun, H.-K., Chinnakali, K., Razak, I. A. & You, X. (1999). Acta Cryst. C55, 573-574.
Kumar, V., Aravamudan, G. & Seshasayee, M. (1990). Acta Cryst. C46, 674-676.
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Von Deuten, K., Schnabel, W. & Klar, G. (1980). Phosphorus Sulfur Silicon Relat. Elem. 9, 93-98.

organic compounds