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Volume 68 
Part 1 
Page o120  
January 2012  

Received 21 November 2011
Accepted 1 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.103
Data-to-parameter ratio = 18.2
Details
Open access

1-Benzoyl-3-(4-n-butylphenyl)thiourea

aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and bDepartment of Chemistry, Faculty of Engineering, Gifu University Yanagido, Gifu 501-1193, Japan
Correspondence e-mail: aminbadshah@yahoo.com

The dihedral angle between the benzoyl and phenyl groups in the title compound, C18H20N2OS, is 30.57 (4)°. The crystal packing is characterized by N-H...O hydrogen bonds. In the crysta, pairs of N-H...S hydrogen bonds link the molecules into inversion dimers

Related literature

For background to our work on the structural chemistry of N,N'-disubstituted thioures and for related structures, see: Khawer Rauf et al. (2009a[Khawar Rauf, M., Bolte, M. & Badshah, A. (2009a). Acta Cryst. E65, o177.],b[Khawar Rauf, M., Bolte, M. & Badshah, A. (2009b). Acta Cryst. E65, o240.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2 pp. S1-19.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C18H20N2OS

  • Mr = 312.42

  • Triclinic, [P \overline 1]

  • a = 4.648 (3) Å

  • b = 13.274 (8) Å

  • c = 13.690 (8) Å

  • [alpha] = 106.765 (7)°

  • [beta] = 90.013 (6)°

  • [gamma] = 92.700 (8)°

  • V = 807.9 (8) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 123 K

  • 0.40 × 0.10 × 0.10 mm

Data collection
  • Rigaku/MSC Mercury CCD diffractometer

  • 6380 measured reflections

  • 3632 independent reflections

  • 3242 reflections with I > 2[sigma](I)

  • Rint = 0.043

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.103

  • S = 1.06

  • 3632 reflections

  • 200 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1 0.88 1.88 2.630 (2) 142
N2-H2...S1i 0.88 2.76 3.550 (2) 151
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001[Molecular Structure Corporation & Rigaku (2001). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.]) and TEXSAN (Molecular Structure Corporation & Rigaku, 2004[Molecular Structure Corporation & Rigaku (2004). TEXSAN. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); software used to prepare material for publication: Yadokari-XG 2009 (Kabuto et al., 2009[Kabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009). J. Crystallogr. Soc. Jpn, 51, 218-224.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5142 ).


Acknowledgements

MKR is grateful to the Quaid-i-Azam University, Islamabad, for financial support for a post-doctoral fellowship.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2 pp. S1-19.
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Kabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009). J. Crystallogr. Soc. Jpn, 51, 218-224.
Khawar Rauf, M., Bolte, M. & Badshah, A. (2009a). Acta Cryst. E65, o177.  [CSD] [CrossRef] [details]
Khawar Rauf, M., Bolte, M. & Badshah, A. (2009b). Acta Cryst. E65, o240.  [CSD] [CrossRef] [details]
Molecular Structure Corporation & Rigaku (2001). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Molecular Structure Corporation & Rigaku (2004). TEXSAN. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o120  [ doi:10.1107/S1600536811051774 ]

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