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Volume 69 
Part 11 
Page o1622  
November 2013  

Received 3 October 2013
Accepted 4 October 2013
Online 9 October 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.109
Data-to-parameter ratio = 25.0
Details
Open access

N-(1,3-Benzo­thia­zol-2-yl)acetamide

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

The title compound, C9H8N2OS, crystallizes with two mol­ecules (A and B) in the asymmetric unit. The dihedral angles between the mean planes of the 1,3-benzo­thia­zol-2-yl ring system and the acetamide group are 2.7 (4) (mol­ecule A) and 7.2 (2) Å (mol­ecule B). In the crystal, pairs of N-H...N hydrogen bonds link the A and B mol­ecules into dimers, generating R22(8) loops. The dimers stack along [100].

Related literature

For the related crystal structure of the acetamide derivatives, see: Jasinski et al. (2013[Jasinski, J. P., Guild, C. J., Yathirajan, H. S., Narayana, B. & Samshuddin, S. (2013). Acta Cryst. E69, o461.]); Fun et al. (2011a[Fun, H.-K., Quah, C. K., Narayana, B., Nayak, P. S. & Sarojini, B. K. (2011a). Acta Cryst. E67, o2926-o2927.],b[Fun, H.-K., Quah, C. K., Narayana, B., Nayak, P. S. & Sarojini, B. K. (2011b). Acta Cryst. E67, o2941-o2942.], 2012[Fun, H.-K., Loh, W.-S., Shetty, D. N., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o1348.]).

[Scheme 1]

Experimental

Crystal data
  • C9H8N2OS

  • Mr = 192.24

  • Monoclinic, P 21 /c

  • a = 11.1852 (4) Å

  • b = 7.4037 (4) Å

  • c = 20.9189 (8) Å

  • [beta] = 94.408 (3)°

  • V = 1727.21 (13) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.33 mm-1

  • T = 173 K

  • 0.45 × 0.24 × 0.15 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.])Tmin = 0.770, Tmax = 1.000

  • 20845 measured reflections

  • 5918 independent reflections

  • 4622 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.109

  • S = 1.08

  • 5918 reflections

  • 237 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.44 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2A-H2A...N1B 0.86 2.11 2.9700 (16) 176
N2B-H2B...N1A 0.86 2.14 2.9749 (16) 165

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.]); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7144 ).


Acknowledgements

BN thanks the UGC for financial assistance through BSR one time grant for the purchase of chemicals and DST-PURSE for financial assistance. HSY thanks University of Mysore for research facilities. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Fun, H.-K., Loh, W.-S., Shetty, D. N., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o1348.  [CSD] [CrossRef] [IUCr Journals]
Fun, H.-K., Quah, C. K., Narayana, B., Nayak, P. S. & Sarojini, B. K. (2011a). Acta Cryst. E67, o2926-o2927.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Fun, H.-K., Quah, C. K., Narayana, B., Nayak, P. S. & Sarojini, B. K. (2011b). Acta Cryst. E67, o2941-o2942.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Jasinski, J. P., Guild, C. J., Yathirajan, H. S., Narayana, B. & Samshuddin, S. (2013). Acta Cryst. E69, o461.  [CSD] [CrossRef] [IUCr Journals]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1622  [ doi:10.1107/S160053681302730X ]

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