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Volume 69 
Part 5 
Pages o701-o702  
May 2013  

Received 31 March 2013
Accepted 7 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.041
wR = 0.121
Data-to-parameter ratio = 13.7
Details
Open access

N-[4-Acetyl-5-(4-fluorophenyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide

aDepartment of Physics, Government Science College, Hassan 573 201, Karnataka, India,bDepartment of Studies in Chemistry, Karnataka University, Dharwad 580 003, Karnataka , India, and cDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India
Correspondence e-mail: devarajegowda@yahoo.com, kamchem9@gmail.com

The title molecule, C12H12FN3O2S, shows a short intramolecular S...O contact of 2.682 (18) Å. The dihedral angle between the thiadiazole ring and the benzene ring is 86.82 (11)°. In the crystal, N-H...O and C-H...O hydrogen bonds generate an R21(6) graph-set motif between adjacent molecules. Pairs of futher C-H...O hydrogen bonds form inversion dimers with R22(8) ring motifs. These combine to generate a three-dimensional network and stack the molecules along the b axis.

Related literature

For biological applications of 1,3,4-thiadiazole derivatives, see: Matysiak & Opolski (2006[Matysiak, J. & Opolski, A. (2006). Bioorg. Med. Chem. 14, 4483-4489.]); Kumar et al. (2012[Kumar, D. N., Kumar, M., Noel, B. & Shah, K. (2012). Eur. J. Med. Chem. 55, 432-438.]); Oruç et al. (2004[Oruç, E. E., Rollas, S., Kkandemirli, F., Shvets, N. & Dimoglo, A. S. (2004). J. Med. Chem. 47, 6760-6767.]); Kadi et al. (2007[Kadi, A. A., El-Brollosy, N. R., Al-Deeb, O. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2007). Eur. J. Med. Chem. 42, 235-242.]); Noolvi et al. (2011[Noolvi, M. N., Patel, H. M., Singh, N., Gadad, A. K., Cameotra, S. S. & Badiger, A. (2011). Eur. J. Med. Chem. 46, 4411-4418.]); Matysiak et al. (2006[Matysiak, J., Nasulewicz, A., Peiczynska, M., Switalska, M., Jarozewicz, I. & Opolski, A. (2006). Eur. J. Med. Chem. 41, 475-482.]); Marganakop et al. (2012[Marganakop, S. B., Kamble, R. R., Taj, T. & Kariduraganvar, M. Y. (2012). Med. Chem. Res. 21, 185-191.]). For a related structure, see: Zhang (2009[Zhang, G.-Y. (2009). Acta Cryst. E65, o2138.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C12H12FN3O2S

  • Mr = 281.31

  • Monoclinic, P 21 /c

  • a = 9.5061 (6) Å

  • b = 11.2152 (7) Å

  • c = 12.7752 (7) Å

  • [beta] = 101.823 (4)°

  • V = 1333.11 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 296 K

  • 0.24 × 0.20 × 0.12 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.770, Tmax = 1.000

  • 11372 measured reflections

  • 2352 independent reflections

  • 2035 reflections with I > 2[sigma](I)

  • Rint = 0.024

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

  • wR(F2) = 0.121

  • S = 1.07

  • 2352 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N5-H5...O4i 0.86 1.96 2.815 (2) 171
C10-H10...O3ii 0.93 2.58 3.267 (3) 131
C17-H17A...O4i 0.96 2.46 3.316 (3) 148
C19-H19B...O4iii 0.96 2.55 3.335 (3) 139
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5314 ).


Acknowledgements

The authors thank the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for the X-ray data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kadi, A. A., El-Brollosy, N. R., Al-Deeb, O. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2007). Eur. J. Med. Chem. 42, 235-242.  [ISI] [CrossRef] [PubMed] [ChemPort]
Kumar, D. N., Kumar, M., Noel, B. & Shah, K. (2012). Eur. J. Med. Chem. 55, 432-438.  [ISI] [CrossRef] [ChemPort] [PubMed]
Marganakop, S. B., Kamble, R. R., Taj, T. & Kariduraganvar, M. Y. (2012). Med. Chem. Res. 21, 185-191.  [ISI] [CrossRef] [ChemPort]
Matysiak, J., Nasulewicz, A., Peiczynska, M., Switalska, M., Jarozewicz, I. & Opolski, A. (2006). Eur. J. Med. Chem. 41, 475-482.  [ISI] [CrossRef] [PubMed] [ChemPort]
Matysiak, J. & Opolski, A. (2006). Bioorg. Med. Chem. 14, 4483-4489.  [CrossRef] [PubMed] [ChemPort]
Noolvi, M. N., Patel, H. M., Singh, N., Gadad, A. K., Cameotra, S. S. & Badiger, A. (2011). Eur. J. Med. Chem. 46, 4411-4418.  [ISI] [CrossRef] [ChemPort] [PubMed]
Oruç, E. E., Rollas, S., Kkandemirli, F., Shvets, N. & Dimoglo, A. S. (2004). J. Med. Chem. 47, 6760-6767.  [ISI] [PubMed]
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Zhang, G.-Y. (2009). Acta Cryst. E65, o2138.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o701-o702   [ doi:10.1107/S1600536813009367 ]

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