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Volume 69 
Part 5 
Pages o645-o646  
May 2013  

Received 26 March 2013
Accepted 26 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
R = 0.047
wR = 0.118
Data-to-parameter ratio = 36.3
Details
Open access

2-(3,4-Dichlorophenyl)-N-(1,3-thiazol-2-yl)acetamide

aDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India,bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,cDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and dDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C11H8Cl2N2OS, the mean plane of the dichlorophenyl ring is twisted by 61.8 (1)° from that of the thiazole ring. In the crystal, molecules are linked via pairs of N-H...N hydrogen bonds with an R22(8) graph-set motif, forming inversion dimers which stack along the a-axis direction.

Related literature

For the structural similarity of N-substituted 2-arylacetamides to the lateral chain of natural benzylpenicillin, see: Mijin & Marinkovic (2006[Mijin, D. & Marinkovic, A. (2006). Synth. Commun. 36, 193-198.]); Mijin et al. (2008[Mijin, D. Z., Prascevic, M. & Petrovic, S. D. (2008). J. Serb. Chem. Soc. 73, 945-950.]). For the coordination abilities of amides, see: Wu et al. (2008[Wu, W.-N., Cheng, F.-X., Yan, L. & Tang, N. (2008). J. Coord. Chem. 61, 2207-2215.], 2010[Wu, W.-N., Wang, Y., Zhang, A.-Y., Zhao, R.-Q. & Wang, Q.-F. (2010). Acta Cryst. E66, m288.]). For related structures, see: Fun et al. (2012a[Fun, H.-K., Ooi, C. W., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012a). Acta Cryst. E68, o1312-o1313.],b[Fun, H.-K., Quah, C. K., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012b). Acta Cryst. E68, o2679.],c[Fun, H.-K., Quah, C. K., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012c). Acta Cryst. E68, o2464.],d[Fun, H.-K., Quah, C. K., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012d). Acta Cryst. E68, o2461.],e[Fun, H.-K., Quah, C. K., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012e). Acta Cryst. E68, o2565.]); Butcher et al. (2013a[Butcher, R. J., Mahan, A., Nayak, P. S., Narayana, B. & Yathirajan, H. S. (2013a). Acta Cryst. E69, o46-o47.],b[Butcher, R. J., Mahan, A., Nayak, P. S., Narayana, B. & Yathirajan, H. S. (2013b). Acta Cryst. E69, o39.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C11H8Cl2N2OS

  • Mr = 287.15

  • Triclinic, [P \overline 1]

  • a = 4.6185 (3) Å

  • b = 7.7741 (7) Å

  • c = 17.1188 (12) Å

  • [alpha] = 100.278 (7)°

  • [beta] = 94.250 (6)°

  • [gamma] = 105.001 (7)°

  • V = 579.47 (8) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.72 mm-1

  • T = 123 K

  • 0.55 × 0.19 × 0.12 mm

Data collection
  • Agilent Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: analytical (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.776, Tmax = 0.929

  • 9162 measured reflections

  • 5597 independent reflections

  • 3860 reflections with I > 2[sigma](I)

  • Rint = 0.151

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.118

  • S = 1.01

  • 5597 reflections

  • 154 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.64 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...N2i 0.88 2.03 2.8946 (16) 169
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5311 ).


Acknowledgements

BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. PSN thanks Mangalore University for research facilities and the DST-PURSE financial assistance. RJB acknowledges the NSF-MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Butcher, R. J., Mahan, A., Nayak, P. S., Narayana, B. & Yathirajan, H. S. (2013a). Acta Cryst. E69, o46-o47.  [CSD] [CrossRef] [ChemPort] [details]
Butcher, R. J., Mahan, A., Nayak, P. S., Narayana, B. & Yathirajan, H. S. (2013b). Acta Cryst. E69, o39.  [CSD] [CrossRef] [details]
Fun, H.-K., Ooi, C. W., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012a). Acta Cryst. E68, o1312-o1313.  [CSD] [CrossRef] [ChemPort] [details]
Fun, H.-K., Quah, C. K., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012b). Acta Cryst. E68, o2679.  [CSD] [CrossRef] [details]
Fun, H.-K., Quah, C. K., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012c). Acta Cryst. E68, o2464.  [CSD] [CrossRef] [details]
Fun, H.-K., Quah, C. K., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012d). Acta Cryst. E68, o2461.  [CSD] [CrossRef] [details]
Fun, H.-K., Quah, C. K., Nayak, P. S., Narayana, B. & Sarojini, B. K. (2012e). Acta Cryst. E68, o2565.  [CSD] [CrossRef] [details]
Mijin, D. & Marinkovic, A. (2006). Synth. Commun. 36, 193-198.  [ISI] [CrossRef] [ChemPort]
Mijin, D. Z., Prascevic, M. & Petrovic, S. D. (2008). J. Serb. Chem. Soc. 73, 945-950.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Wu, W.-N., Cheng, F.-X., Yan, L. & Tang, N. (2008). J. Coord. Chem. 61, 2207-2215.  [ISI] [CrossRef] [ChemPort]
Wu, W.-N., Wang, Y., Zhang, A.-Y., Zhao, R.-Q. & Wang, Q.-F. (2010). Acta Cryst. E66, m288.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o645-o646   [ doi:10.1107/S1600536813008374 ]

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