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Volume 69 
Part 6 
Page o923  
June 2013  

Received 3 May 2013
Accepted 13 May 2013
Online 18 May 2013

Key indicators
Single-crystal X-ray study
T = 308 K
Mean [sigma](C-C) = 0.002 Å
R = 0.034
wR = 0.099
Data-to-parameter ratio = 18.0
Details
Open access

3-Benzoyl-1-[4-(methylsulfanyl)phenyl]thiourea

aInstituto de Física-UFG, Caixa Postal 131, 74001-970 Goiânia, GO, Brazil,bDepartamento de Química-UEL, Caixa Postal 6001, 86051-990 Londrina, PR, Brazil, and cDepartamento de Química-UFMG, 31270-901 Belo Horizonte, MG, Brazil
Correspondence e-mail: rosanepc@posgrad.ufg.br

The title compound, C15H14N2OS2, adopts a helix conformation. An intramolecular N-H...O hydrogen bond leads to a six-membered pseudo-ring [r.m.s. deviation = 0.0212 Å, maximum deviation = 0.033 (1) Å for the N atom bearing the benzoyl group] in the central unit. The benzene and (methylsulfanyl)benzene ring [r.m.s = 0.0028 Å and largest deviation of 0.067 (3) Å for the methylsulfanyl C atom] make dihedral angles of 31.76 (8) and 54.68 (6)°, respectively, with the pseudo-ring plane. The dihedral angle between the benzene rings is 85.71 (8)°. In the crystal, pairs of weak N-H...S interactions form inversion dimers and mediate a linear chain along [001].

Related literature

For related compounds found in CSD (Allen, 2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]) see: Al-abbasi et al. (2010[Al-abbasi, A. A., Tan, S. S. & Kassim, M. B. (2010). Acta Cryst. E66, o3181.]); Cao et al. (1996[Cao, Y., Zhao, B., Zhang, Y.-Q. & Zhang, D.-C. (1996). Acta Cryst. C52, 1772-1774.]). For the structure of the unsubstituted compound, see: Yamin & Yusof (2003[Yamin, B. M. & Yusof, M. S. M. (2003). Acta Cryst. E59, o151-o152.]). For details of the synthesis, see: Zhang et al. (2001[Zhang, Y.-M., Wei, T.-B. & Gao, L.-M. (2001). Synth. Commun. 31, 3099-3105.]).

[Scheme 1]

Experimental

Crystal data
  • C15H14N2OS2

  • Mr = 302.42

  • Triclinic, [P \overline 1]

  • a = 5.9131 (2) Å

  • b = 9.5826 (3) Å

  • c = 13.3149 (4) Å

  • [alpha] = 96.729 (1)°

  • [beta] = 91.533 (1)°

  • [gamma] = 94.503 (1)°

  • V = 746.46 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.35 mm-1

  • T = 308 K

  • 0.7 × 0.34 × 0.24 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.917, Tmax = 1.0

  • 11518 measured reflections

  • 3285 independent reflections

  • 2908 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.099

  • S = 1

  • 3285 reflections

  • 183 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...O1 0.86 1.93 2.6250 (16) 137
N1-H1...S1i 0.86 2.61 3.4358 (12) 161
Symmetry code: (i) -x+1, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. 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: SHELXL97 (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.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QM2097 ).


Acknowledgements

This work includes part of the activities developed by the Network of Studies for the Development of Novel Inhibitors of Urease, being financed by CNPq (562479/2010-4) and FAPEMIG (APQ-04781-10). The authors are also grateful to CNPq (TOB) and CAPES (RPC) for providing their respective fellowships.

References

Al-abbasi, A. A., Tan, S. S. & Kassim, M. B. (2010). Acta Cryst. E66, o3181.  [CSD] [CrossRef] [details]
Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cao, Y., Zhao, B., Zhang, Y.-Q. & Zhang, D.-C. (1996). Acta Cryst. C52, 1772-1774.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Yamin, B. M. & Yusof, M. S. M. (2003). Acta Cryst. E59, o151-o152.  [CSD] [CrossRef] [ChemPort] [details]
Zhang, Y.-M., Wei, T.-B. & Gao, L.-M. (2001). Synth. Commun. 31, 3099-3105.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o923  [ doi:10.1107/S1600536813013159 ]

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