3-Acetyl-1-(4-methyl­phen­yl)thio­urea

Gowda, B.T.; Foro, S.; Kumar, S.

doi:10.1107/S1600536812026244

Volume 68
Part 7
Page o2128
July 2012

Received 5 June 2012
Accepted 10 June 2012
Online 16 June 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.112
Data-to-parameter ratio = 16.7
Details

3-Acetyl-1-(4-methylphenyl)thiourea

B. Thimme Gowda,^a ^* Sabine Foro ^b and Sharatha Kumar ^a

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
Correspondence e-mail: gowdabt@yahoo.com

The asymmetric unit of the title compound, C₁₀H₁₂N₂OS, contains two independent molecules. In both molecules, the conformations of the two N-H bonds are anti to each other. Furthermore, the conformations of the amide C=S bonds and the C=O bonds are anti to each other. The dihedral angles between the benzene ring and the side chain are 52.8 (1) and 68.0 (1)° in the two independent molecules. An intramolecular N-HO hydrogen bond occurs in both independent molecules. In the crystal, molecules are linked into infinite chains along the a axis through a series of N-HO and N-HS hydrogen bonds.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda & Weiss (1994); Shahwar et al. (2012), of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007), of N-(aryl)-arylsulfonamides, see: Gowda et al. (2005) and of N-chloroarylsulfonamides, see: Jyothi & Gowda (2004); Shetty & Gowda (2004).

Experimental

Crystal data

C₁₀H₁₂N₂OS
M_r = 208.28
Triclinic, $[P \overline 1]$
a = 9.1623 (8) Å
b = 10.130 (1) Å
c = 13.446 (1) Å
= 73.212 (9)°
= 70.276 (8)°
= 66.772 (8)°
V = 1061.90 (16) Å³
Z = 4
Mo K radiation
= 0.27 mm^-1
T = 293 K
0.36 × 0.32 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.908, T_max = 0.937
7674 measured reflections
4293 independent reflections
3267 reflections with I > 2(I)
R_int = 0.013

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.112
S = 1.00
4293 reflections
257 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.17 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO1	0.84	2.02	2.674 (2)	134
N1-H1NO2ⁱ	0.84	2.47	3.198 (2)	145
N2-H2NS2ⁱⁱ	0.84	2.68	3.5058 (17)	169
N3-H3NO2	0.86	1.97	2.661 (2)	137
N3-H3NO1ⁱ	0.86	2.42	3.131 (2)	140
N4-H4NS1ⁱⁱ	0.85	2.57	3.4078 (17)	169
Symmetry codes: (i) -x, -y+2, -z; (ii) -x+1, -y+1, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2284 ).

Acknowledgements

BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC-BSR one-time grant to faculty.

References

Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2337.
Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch. Teil A, 60, 106-112.
Gowda, B. T. & Weiss, A. (1994). Z. Naturforsch. Teil A, 49, 695-702.
Jyothi, K. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 64-68.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Shahwar, D., Tahir, M. N., Chohan, M. M., Ahmad, N. & Raza, M. A. (2012). Acta Cryst. E68, o1160.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shetty, M. & Gowda, B. T. (2004). Z. Naturforsch. Teil B, 59, 63-72.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds