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Volume 69 
Part 8 
Page o1220  
August 2013  

Received 18 June 2013
Accepted 2 July 2013
Online 10 July 2013

Key indicators
Single-crystal X-ray study
T = 292 K
Mean [sigma](C-C) = 0.008 Å
Disorder in main residue
R = 0.076
wR = 0.230
Data-to-parameter ratio = 14.4
Details
Open access

1-(2-Chlorophenyl)-3-(2-ethylhexanoyl)thiourea

aDepartment of Physics, Government Arts College for Women (Autonomous), Pudukkottai 622 001, India,bDepartment of Physics, Kalasalingam University, Krishnankoil 626 126, India,cDepartment of Physics and Nanotechnology, SRM University, Kattankulathur 603 203, India,dDepartment of Chemistry, Government Arts College, Karaikudi 630 303, India, and eSchool of Chemical Sciences and Food Technology, Kebangsaan Universiti, Bangi, Selangor 43650, Malaysia
Correspondence e-mail: santhasrinithi@yahoo.co.in

In the title compound, C15H21ClN2OS, the central chromophore moiety (C2N2OS) is approximately planar, with a maximum deviation of -0.027 (1) Å, and is oriented at a dihedral angle of 86.7 (1)° with respect to the chlorophenyl ring. An intramolecular N-H...O hydrogen bond stabilizes the molecular conformation. In the crystal, molecules associate via N-H...S hydrogen bonds, forming inversion dimers with motif R22(8). These dimers are further connected by N-H...O hydrogen bonds, forming R22(12) dimers. As a result, hydrogen-bonded chains running along [110] are formed. C-H...S interactions also occur. The terminal two C atoms of the butyl chain are disordered over two positions with an occupancy ratio of 0.54:0.46.

Related literature

For general background to the biological activity of thiourea derivatives, see: Yang et al. (2012[Yang, W., Liu, H., Li, M., Wang, F., Zhou, W. & Fan, J. (2012). J. Inorg. Biochem. 116, 97-105.]); Wu et al. (2012[Wu, J., Shi, Q., Chen, Z., He, M., Jin, L. & Hu, D. (2012). Molecules, 17, 5139-5150.]); Abbas et al. (2013[Abbas, S. Y., El-Sharief, M. A., Basyouni, W. M., Fakhr, I. M. & El-Gammal, E. W. (2013). Eur. J. Med. Chem. 64, 111-120.]); Ryu et al. (2012[Ryu, B. J., Hwang, M. K., Park, M., Lee, K. & Kim, S. H. (2012). Bioorg. Med. Chem. Lett. 22, 3862-3865.]).

[Scheme 1]

Experimental

Crystal data
  • C15H21ClN2OS

  • Mr = 312.85

  • Triclinic, [P \overline 1]

  • a = 7.264 (5) Å

  • b = 10.056 (7) Å

  • c = 11.935 (9) Å

  • [alpha] = 97.748 (17)°

  • [beta] = 98.100 (17)°

  • [gamma] = 103.72 (2)°

  • V = 825.5 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.36 mm-1

  • T = 292 K

  • 0.22 × 0.20 × 0.18 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • 8136 measured reflections

  • 2878 independent reflections

  • 1700 reflections with I > 2[sigma](I)

  • Rint = 0.067

Refinement
  • R[F2 > 2[sigma](F2)] = 0.076

  • wR(F2) = 0.230

  • S = 1.02

  • 2878 reflections

  • 200 parameters

  • 4 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.37 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
N1-H1...O1 0.86 1.98 2.652 (4) 134
N1-H1...O1i 0.86 2.49 3.184 (5) 139
N2-H2...S1ii 0.86 2.61 3.451 (4) 168
C9-H9...S1ii 0.98 2.81 3.725 (5) 157
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+2, -z.

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: SHELXL2013 (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.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97 and PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6917 ).


References

Abbas, S. Y., El-Sharief, M. A., Basyouni, W. M., Fakhr, I. M. & El-Gammal, E. W. (2013). Eur. J. Med. Chem. 64, 111-120.  [CrossRef] [ChemPort] [PubMed]
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Ryu, B. J., Hwang, M. K., Park, M., Lee, K. & Kim, S. H. (2012). Bioorg. Med. Chem. Lett. 22, 3862-3865.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Wu, J., Shi, Q., Chen, Z., He, M., Jin, L. & Hu, D. (2012). Molecules, 17, 5139-5150.  [CrossRef] [ChemPort] [PubMed]
Yang, W., Liu, H., Li, M., Wang, F., Zhou, W. & Fan, J. (2012). J. Inorg. Biochem. 116, 97-105.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1220  [ doi:10.1107/S160053681301828X ]

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