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Volume 69 
Part 12 
Page o1815  
December 2013  

Received 18 November 2013
Accepted 19 November 2013
Online 23 November 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.041
wR = 0.114
Data-to-parameter ratio = 13.4
Details
Open access

N-(Adamantan-1-yl)-1,2,3,4-tetra­hydro­iso­quinoline-2-carbo­thio­amide

aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riaydh 11451, Saudi Arabia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hfun.c@ksu.edu.sa

In the title compound, C20H26N2S, the N-containing six-membered ring adopts a boat conformation and the dihedral angle between the thio­carbamide group and the benzene ring is 49.67 (9)°. An intra­molecular C-H...S hydrogen bond generates an S(6) ring motif. The N-H group is sterically hindered and there are no significant inter­molecular inter­actions beyond van der Waals contacts.

Related literature

For related structures and biological background, see: Al-Abdullah et al. (2012[Al-Abdullah, E. S., Asiri, H. H., El-Emam, A. A. & Ng, S. W. (2012). Acta Cryst. E68, o531.]); El-Emam et al. (2012[El-Emam, A. A., El-Brollosy, N. R., Ghabbour, H. A., Quah, C. K. & Fun, H.-K. (2012). Acta Cryst. E68, o1347.]); Al-Tamimi et al. (2013[Al-Tamimi, A.-M. S., Alafeefy, A. M., El-Emam, A. A., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o683.]).

[Scheme 1]

Experimental

Crystal data
  • C20H26N2S

  • Mr = 326.49

  • Monoclinic, P 21 /c

  • a = 19.1707 (5) Å

  • b = 6.4106 (2) Å

  • c = 14.2838 (3) Å

  • [beta] = 103.366 (2)°

  • V = 1707.87 (8) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 1.67 mm-1

  • T = 296 K

  • 0.81 × 0.13 × 0.05 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.345, Tmax = 0.921

  • 10894 measured reflections

  • 2831 independent reflections

  • 2351 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.114

  • S = 1.07

  • 2831 reflections

  • 212 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C16-H16B...S1 0.97 2.72 3.365 (2) 125

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7163 ).


Acknowledgements

The financial support of the Deanship of Scientific Research and the Research Center for Female Scientific and Medical Colleges, King Saud University, is greatly appreciated. CSCK thanks Universiti Sains Malaysia for a postdoctoral research fellowship.

References

Al-Abdullah, E. S., Asiri, H. H., El-Emam, A. A. & Ng, S. W. (2012). Acta Cryst. E68, o531.  [CSD] [CrossRef] [IUCr Journals]
Al-Tamimi, A.-M. S., Alafeefy, A. M., El-Emam, A. A., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o683.  [CSD] [CrossRef] [IUCr Journals]
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
El-Emam, A. A., El-Brollosy, N. R., Ghabbour, H. A., Quah, C. K. & Fun, H.-K. (2012). Acta Cryst. E68, o1347.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1815  [ doi:10.1107/S1600536813031516 ]

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