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

Rauf, M.; Ebihara, M.; Badshah, A.; Imtiaz-ud-Din

doi:10.1107/S1600536811051774

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 (C-C) = 0.002 Å
R = 0.043
wR = 0.103
Data-to-parameter ratio = 18.2
Details

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

M. Khawar Rauf,^a Masahiro Ebihara,^b Amin Badshah ^a ^* and Imtiaz-ud-Din ^a

^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-HO hydrogen bonds. In the crysta, pairs of N-HS 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,b). For bond-length data, see: Allen et al. (1987). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental

Crystal data

C₁₈H₂₀N₂OS
M_r = 312.42
Triclinic, $[P \overline 1]$
a = 4.648 (3) Å
b = 13.274 (8) Å
c = 13.690 (8) Å
= 106.765 (7)°
= 90.013 (6)°
= 92.700 (8)°
V = 807.9 (8) Å³
Z = 2
Mo K radiation
= 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(I)
R_int = 0.043

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.103
S = 1.06
3632 reflections
200 parameters
H-atom parameters constrained
_max = 0.33 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1	0.88	1.88	2.630 (2)	142
N2-H2S1ⁱ	0.88	2.76	3.550 (2)	151
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and TEXSAN (Molecular Structure Corporation & Rigaku, 2004); software used to prepare material for publication: Yadokari-XG 2009 (Kabuto et al., 2009).

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.
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.
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.
Khawar Rauf, M., Bolte, M. & Badshah, A. (2009b). Acta Cryst. E65, o240.
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.

organic compounds