1-(2-Chloro­benzo­yl)-3-(3-meth­oxy­phen­yl)thio­urea

Rauf, M.K.; Ebihara, M.; Badshah, A.

doi:10.1107/S1600536812048830

Volume 69
Part 1
Page o19
January 2013

Received 19 November 2012
Accepted 28 November 2012
Online 5 December 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.002 Å
R = 0.035
wR = 0.088
Data-to-parameter ratio = 16.9
Details

1-(2-Chlorobenzoyl)-3-(3-methoxyphenyl)thiourea

M. Khawar Rauf,^a Masahiro Ebihara ^b and Amin Badshah ^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, mkhawarrauf@yahoo.co.uk

The title compound, C₁₅H₁₃ClN₂O₂S, exists in the solid state in its thione form with typical thiourea C-S and C-O bonds lengths as well as shortened C-N bonds. An intramolecular N-HO hydrogen bond stabilizes the molecular conformation. In the crystal, N-HS hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For previous work on N,N'-disubstituted thioureas, see: Rauf et al. (2012). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental

Crystal data

C₁₅H₁₃ClN₂O₂S
M_r = 320.78
Triclinic, $[P \overline 1]$
a = 6.276 (3) Å
b = 10.202 (5) Å
c = 11.411 (5) Å
= 94.541 (7)°
= 93.305 (6)°
= 96.918 (7)°
V = 721.3 (6) Å³
Z = 2
Mo K radiation
= 0.41 mm^-1
T = 123 K
0.45 × 0.36 × 0.20 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer
5698 measured reflections
3222 independent reflections
3071 reflections with I > 2(I)
R_int = 0.052

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.088
S = 1.09
3222 reflections
191 parameters
H-atom parameters constrained
_max = 0.33 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O1	0.88	1.95	2.6500 (17)	135
N1-H1S1ⁱ	0.88	2.64	3.4080 (17)	146
Symmetry code: (i) -x+1, -y+1, -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); software used to prepare material for publication: Yadokari-XG (Wakita, 2001; Kabuto et al., 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: MW2100 ).

Acknowledgements

MKR is grateful to The Quaid-i-Azam University, Islamabad for financial support for a postdoctoral fellowship.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.
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.
Molecular Structure Corporation & Rigaku (2001). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Rauf, M. K., Ebihara, M., Badshah, A. & Imtiaz-ud-Din (2012). Acta Cryst. E68, o120.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wakita, K. (2001). Yadokari-XG. http://www.hat.hi-ho.ne.jp/k-wakita/yadokari .

organic compounds