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Volume 69 
Part 9 
Page o1472  
September 2013  

Received 17 August 2013
Accepted 19 August 2013
Online 23 August 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
R = 0.049
wR = 0.115
Data-to-parameter ratio = 15.5
Details
Open access

2-(Adamantan-1-yl)-N-(6-methoxy-1,3-benzothiazol-2-yl)acetamide

aDepartment of Chemistry and Chemical Technology, Togliatti State University, 14 Belorusskaya St, Togliatti 445667, Russian Federation,bDepartment of Organic, Bioorganic and Medicinal Chemistry, Samara State University, 1 Academician Pavlov St, Samara 443011, Russian Federation, and cX-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, B-334, Moscow 119991, Russian Federation
Correspondence e-mail: a.s.bunev@gmail.com

The asymmetric unit of the title compound, C20H24N2O2S, contains two independent molecules having very similar geometries. The main N-(6-methoxy-1,3-benzothiazol-2-yl)acetamide moiety adopts an almost planar structure (r.m.s. deviations of 0.091 and 0.051 Å for the two independent molecules). The adamantyl substituent occupies the gauche position relative to the C-N bond of the acetamide moiety [the corresponding N-C-C-C dihedral angles are -100.3 (3) and -96.5 (3)° for the two independent molecules]. In the crystal, the two independent molecules form a dimer via a pair of N-H...N hydrogen bonds. The dimers are further linked by C-H...O hydrogen bonds and attractive S...S [3.622 (2) Å] interactions into ribbons along [100].

Related literature

For properties of benzothiazoles as building blocks in organic synthesis, see: Gupta & Rawat (2010[Gupta, A. & Rawat, S. (2010). J. Curr. Pharm. Res. 3, 13-23.]); Facchinetti et al. (2012[Facchinetti, V., da Reis, R., Gomes, C. R. B. & Vasconcelos, T. R. A. (2012). Mini-Rev. Org. Chem. 9, 44-53.]); Sareen et al. (2012[Sareen, S., Shinde, D., Khatri, V. & Sareen, V. (2012). Heterocycl. Lett. 2, 361-377.]); Radatz et al. (2013[Radatz, C. S., Alves, D. & Schneider, P. H. (2013). Tetrahedron, 69, 1316-1321.]). For syntheses and properties of 2-substituted benzothiazoles, see: Hussein et al. (2012[Hussein, B. H. M., Azab, H. A., El-Azab, M. F. & El-Falouji, A. I. (2012). Eur. J. Med. Chem. 51, 99-109.]); Ugale et al. (2012[Ugale, V. G., Patel, H. M., Wadodkar, S. G., Bari, S. B., Shirkhedkar, A. A. & Surana, S. J. (2012). Eur. J. Med. Chem. 53, 107-113.]); Yoo et al. (2012[Yoo, E., Hayat, F., Rhim, H. & Choo, H. P. (2012). Bioorg. Med. Chem. 20, 2707-2712.]); Zhu et al. (2012[Zhu, X. Y., Etukala, J. R., Eyunni, S. V. K., Setola, V., Roth, B. L. & Ablordeppey, S. Y. (2012). Eur. J. Med. Chem. 53, 124-132.]); Bhardwaj et al. (2013[Bhardwaj, V. K., Saluja, P., Hundal, G., Hundal, M. S., Singh, N. & Jang, D. O. (2013). Tetrahedron, 69, 1606-1610.]); Patel et al. (2013[Patel, N. B., Khan, I. H., Pannecouque, C. & De Clercq, E. (2013). Med. Chem. Res. 22, 1320-1329.]).

[Scheme 1]

Experimental

Crystal data
  • C20H24N2O2S

  • Mr = 356.48

  • Triclinic, [P \overline 1]

  • a = 11.0114 (13) Å

  • b = 13.6647 (18) Å

  • c = 13.9230 (18) Å

  • [alpha] = 61.554 (3)°

  • [beta] = 80.252 (3)°

  • [gamma] = 89.782 (4)°

  • V = 1808.3 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 100 K

  • 0.20 × 0.15 × 0.10 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2003[Bruker (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.962, Tmax = 0.981

  • 17897 measured reflections

  • 7124 independent reflections

  • 4424 reflections with I > 2[sigma](I)

  • Rint = 0.071

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.115

  • S = 0.91

  • 7124 reflections

  • 459 parameters

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

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2N...N3 0.87 (3) 2.13 (3) 2.995 (3) 169 (2)
N4-H4N...N1 0.78 (3) 2.30 (3) 3.077 (3) 174 (2)
C6-H6...O3i 0.95 2.58 3.452 (3) 153
C26-H26...O1ii 0.95 2.45 3.392 (3) 174
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). 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.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2412 ).


Acknowledgements

The authors are grateful to the Ministry of Education and Science of the Russian Federation (State program No. 3.1168.2011).

References

Bhardwaj, V. K., Saluja, P., Hundal, G., Hundal, M. S., Singh, N. & Jang, D. O. (2013). Tetrahedron, 69, 1606-1610.  [ISI] [CSD] [CrossRef] [ChemPort]
Bruker (2001). SAINT . Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Facchinetti, V., da Reis, R., Gomes, C. R. B. & Vasconcelos, T. R. A. (2012). Mini-Rev. Org. Chem. 9, 44-53.  [CrossRef] [ChemPort]
Gupta, A. & Rawat, S. (2010). J. Curr. Pharm. Res. 3, 13-23.
Hussein, B. H. M., Azab, H. A., El-Azab, M. F. & El-Falouji, A. I. (2012). Eur. J. Med. Chem. 51, 99-109.  [ISI] [CrossRef] [ChemPort] [PubMed]
Patel, N. B., Khan, I. H., Pannecouque, C. & De Clercq, E. (2013). Med. Chem. Res. 22, 1320-1329.  [ISI] [CrossRef] [ChemPort]
Radatz, C. S., Alves, D. & Schneider, P. H. (2013). Tetrahedron, 69, 1316-1321.  [ISI] [CrossRef] [ChemPort]
Sareen, S., Shinde, D., Khatri, V. & Sareen, V. (2012). Heterocycl. Lett. 2, 361-377.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Ugale, V. G., Patel, H. M., Wadodkar, S. G., Bari, S. B., Shirkhedkar, A. A. & Surana, S. J. (2012). Eur. J. Med. Chem. 53, 107-113.  [ISI] [CrossRef] [ChemPort] [PubMed]
Yoo, E., Hayat, F., Rhim, H. & Choo, H. P. (2012). Bioorg. Med. Chem. 20, 2707-2712.  [CrossRef] [ChemPort] [PubMed]
Zhu, X. Y., Etukala, J. R., Eyunni, S. V. K., Setola, V., Roth, B. L. & Ablordeppey, S. Y. (2012). Eur. J. Med. Chem. 53, 124-132.  [ISI] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1472  [ doi:10.1107/S1600536813023313 ]

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