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Volume 68 
Part 1 
Page o161  
January 2012  

Received 28 November 2011
Accepted 12 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.047
wR = 0.110
Data-to-parameter ratio = 13.8
Details
Open access

(2-Anilino-4-methylthiazol-5-yl)(4-chlorophenyl)methanone

aState Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, People's Republic of China
Correspondence e-mail: xieym@scu.edu.cn

The title compound, C17H13ClN2OS, crystallizes with three independent molecules (A, B and C) in the asymmetric unit which differ slightly in their conformations. In molecule A, the thiazole ring makes dihedral angles of 27.44 (14) and 66.05 (6)° with the phenyl and chlorobenzene rings. In molecule B, the respective angles are 29.09 (10) and 47.63 (9)°, while values of 25.67 (11) and 51.01 (7)° are observed in molecule C. In the crystal, N-H...N and N-H...O hydrogen bonds generate a three-dimensional network structure.

Related literature

For the biological activity and synthesis of phenyl(thiazol-5-yl)methanone derivatives, see: Moisés et al. (2000[Moisés, R., Adriana, A., Raymundo, C., Aydee, F., Rosa, M. & Andrés, P. (2000). J. Org. Chem. 65, 7244-7247.]).

[Scheme 1]

Experimental

Crystal data
  • C17H13ClN2OS

  • Mr = 328.80

  • Monoclinic, P 21 /n

  • a = 22.8350 (6) Å

  • b = 8.0587 (2) Å

  • c = 25.3653 (6) Å

  • [beta] = 90.900 (2)°

  • V = 4667.1 (2) Å3

  • Z = 12

  • Mo K[alpha] radiation

  • [mu] = 0.38 mm-1

  • T = 293 K

  • 0.40 × 0.18 × 0.12 mm

Data collection
  • Agilent Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.909, Tmax = 1.000

  • 18535 measured reflections

  • 8224 independent reflections

  • 5819 reflections with I > 2[sigma](I)

  • Rint = 0.020

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

  • wR(F2) = 0.110

  • S = 1.02

  • 8224 reflections

  • 598 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2A-H2A...O1Ci 0.86 2.09 2.933 (3) 167
N2B-H2B...N1Cii 0.86 2.11 2.962 (3) 170
N2C-H2C...N1Biii 0.86 2.17 2.995 (3) 162
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies Ltd, 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: 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.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2345 ).


Acknowledgements

We thank the Analytical and Testing Center of Sichuan University for the X-ray measurements.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Moisés, R., Adriana, A., Raymundo, C., Aydee, F., Rosa, M. & Andrés, P. (2000). J. Org. Chem. 65, 7244-7247.  [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o161  [ doi:10.1107/S1600536811053463 ]

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