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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 [sigma](C-C) = 0.003 Å
R = 0.038
wR = 0.104
Data-to-parameter ratio = 21.0
Details
Open access

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

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-H...S 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[Von Deuten, K., Schnabel, W. & Klar, G. (1980). Phosphorus Sulfur Silicon Relat. Elem. 9, 93-98.]); Kumar et al. (1990[Kumar, V., Aravamudan, G. & Seshasayee, M. (1990). Acta Cryst. C46, 674-676.]); Fun et al. (2001[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.]). For preparation of the title compound, see: Garg et al. (1993[Garg, B. S., Garg, R. K. & Reddy, M. J. (1993). Indian J. Chem. Sect. A, 32, 697-700.]). For related structures, see: Ivanov et al. (2003[Ivanov, A. V., Larionov, S. A., Forsling, W., Antzutkin, O. N. & Kritikos, M. (2003). Russ. J. Coord. Chem. 29, 142-150]); Jian et al. (1999[Jian, F., Jiang, L., Fun, H.-K., Chinnakali, K., Razak, I. A. & You, X. (1999). Acta Cryst. C55, 573-574.]); Fun et al. (2001[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.]). For ring-puckering parameters, see: Nardelli (1983[Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.]).

[Scheme 1]

Experimental

Crystal data
  • C20H20N2S4

  • Mr = 416.62

  • Monoclinic, P 21 /c

  • a = 8.1019 (4) Å

  • b = 20.3208 (11) Å

  • c = 12.3647 (6) Å

  • [beta] = 104.371 (2)°

  • V = 1971.99 (17) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.867, Tmax = 0.909

  • 44844 measured reflections

  • 4941 independent reflections

  • 4036 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.104

  • S = 1.03

  • 4941 reflections

  • 235 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.53 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-H...A D-H H...A D...A D-H...A
C12-H12B...S4 0.97 2.53 3.028 (2) 112
C18-H18...Cg1i   2.74 3.604 (2) 154
Symmetry code: (i) -x, -y, -z+2.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); 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.  [CrossRef] [details]
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.  [CSD] [CrossRef] [details]
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  [CrossRef] [ChemPort]
Jian, F., Jiang, L., Fun, H.-K., Chinnakali, K., Razak, I. A. & You, X. (1999). Acta Cryst. C55, 573-574.  [CSD] [CrossRef] [details]
Kumar, V., Aravamudan, G. & Seshasayee, M. (1990). Acta Cryst. C46, 674-676.  [CrossRef] [details]
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Von Deuten, K., Schnabel, W. & Klar, G. (1980). Phosphorus Sulfur Silicon Relat. Elem. 9, 93-98.  [ChemPort]


Acta Cryst (2012). E68, o3446  [ doi:10.1107/S1600536812047320 ]

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