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Volume 69 
Part 5 
Page o683  
May 2013  

Received 2 April 2013
Accepted 3 April 2013
Online 10 April 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
R = 0.054
wR = 0.144
Data-to-parameter ratio = 19.0
Details
Open access

5-(Adamantan-1-yl)-N-methyl-1,3,4-thiadiazol-2-amine

aDepartment of Pharmaceutical Chemistry, College of Pharmacy, Salman bin Abdulaziz University, Alkharj 11942, Saudi Arabia,bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia,cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and dChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: edward.tiekink@gmail.com

In the title compound, C13H19N3S, the methylamine substituent is coplanar with the thiadiazole ring to which it is attached [C-N-C-S torsion angle = 175.9 (2)°] and the amine H atom is syn to the thiadiazole S atom. Supramolecular chains along [101], sustained by N-H...N hydrogen bonding, feature in the crystal packing.

Related literature

For the biological activity of 1,3,4-thiadiazol-2-amine derivatives, see: Carvalho et al. (2008[Carvalho, S. A., Lopes, F. A. S., Salomão, K., Romeiro, N. C., Wardell, S. M. S. V., de Castro, S. L., da Silva, E. F. & Fraga, C. A. M. (2008). Bioorg. Med. Chem. 16, 413-421.]); Foroumadi et al. (1999[Foroumadi, A., Daneshtalab, M. & Shafiee, A. (1999). Arzneim.-Forsch. Drug. Res. 49, 1035-1038.]), and of adamantane derivatives, see: Togo et al. (1968[Togo, Y., Hornick, R. B. & Dawkins, A. T. (1968). J. Am. Med. Assoc. 203, 1089-1094.]); El-Emam et al. (2004[El-Emam, A. A., Al-Deeb, O. A., Al-Omar, M. A. & Lehmann, J. (2004). Bioorg. Med. Chem. 12, 5107-5113.]). For related structures, see: El-Emam et al. (2012[El-Emam, A. A., Kadi, A. A., El-Brollosy, N. R., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o795.]); Almutairi et al. (2012[Almutairi, M. S., Al-Shehri, M. M., El-Emam, A. A., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o656.]). For the synthesis of the title compound, see: El-Emam & Lehmann (1994[El-Emam, A. A. & Lehmann, J. (1994). Monatsh. Chem. 125, 587-591.]).

[Scheme 1]

Experimental

Crystal data
  • C13H19N3S

  • Mr = 249.37

  • Monoclinic, P 21 /n

  • a = 10.4394 (12) Å

  • b = 13.0910 (13) Å

  • c = 10.8871 (15) Å

  • [beta] = 118.008 (16)°

  • V = 1313.6 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.23 mm-1

  • T = 295 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.887, Tmax = 1.000

  • 6791 measured reflections

  • 3027 independent reflections

  • 1975 reflections with I > 2[sigma](I)

  • Rint = 0.039

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.144

  • S = 1.04

  • 3027 reflections

  • 159 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3...N1i 0.87 (1) 2.15 (1) 3.021 (3) 179 (2)
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5305 ).


Acknowledgements

The financial support of the Deanship of Scientific Research, Salman bin Abdulaziz University, Alkharj, Saudi Arabia, is greatly appreciated. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/03).

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Almutairi, M. S., Al-Shehri, M. M., El-Emam, A. A., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o656.  [CSD] [CrossRef] [details]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Carvalho, S. A., Lopes, F. A. S., Salomão, K., Romeiro, N. C., Wardell, S. M. S. V., de Castro, S. L., da Silva, E. F. & Fraga, C. A. M. (2008). Bioorg. Med. Chem. 16, 413-421.  [CSD] [CrossRef] [PubMed] [ChemPort]
El-Emam, A. A., Al-Deeb, O. A., Al-Omar, M. A. & Lehmann, J. (2004). Bioorg. Med. Chem. 12, 5107-5113.  [CrossRef] [PubMed] [ChemPort]
El-Emam, A. A., Kadi, A. A., El-Brollosy, N. R., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o795.  [CSD] [CrossRef] [details]
El-Emam, A. A. & Lehmann, J. (1994). Monatsh. Chem. 125, 587-591.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Foroumadi, A., Daneshtalab, M. & Shafiee, A. (1999). Arzneim.-Forsch. Drug. Res. 49, 1035-1038.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Togo, Y., Hornick, R. B. & Dawkins, A. T. (1968). J. Am. Med. Assoc. 203, 1089-1094.  [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o683  [ doi:10.1107/S1600536813009033 ]

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