N-(3-Chloro­propion­yl)-N′-phenyl­thio­urea

Othman, E.A.; Soh, S.K.C.; Yamin, B.M.

doi:10.1107/S1600536810005271

Volume 66
Part 3
Page o628
March 2010

Received 27 January 2010
Accepted 9 February 2010
Online 13 February 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.041
wR = 0.113
Data-to-parameter ratio = 15.5
Details

N-(3-Chloropropionyl)-N'-phenylthiourea

Eliyanti A. Othman,^a Siti K. C. Soh ^a and Bohari M. Yamin ^a ^*

^aSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, UKM 43500 Bangi Selangor, Malaysia
Correspondence e-mail: bohari@ukm.my

The title compound, C₁₀H₁₁ClN₂OS, adopts a cis-trans configuration with respect to the position of the phenyl and 3-chloropropionyl groups relative to the thiono group across the C-N bonds. The benzene ring is perpendicular to the propionyl thiourea fragment with a dihedral angle of 82.62 (10)°. An intramolecular N-HO interaction occurs. The crystal structure is stabilized by intermolecular N-HS hydrogen bonds, which link pairs of molecules, building up R₂²(8) ring motifs, and C-H.. [pi] interactions.

Related literature

For related structures, see: Ismail et al. (2007); Ismail & Yamin (2009). For hydrogen-bond motifs, see: Etter et al.(1990); Bernstein et al. (1995). For reference bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₁₀H₁₁ClN₂OS
M_r = 242.72
Triclinic, $[P \overline 1]$
a = 5.8088 (12) Å
b = 10.467 (2) Å
c = 10.660 (2) Å
= 112.811 (3)°
= 101.855 (3)°
= 95.483 (3)°
V = 573.6 (2) Å³
Z = 2
Mo K radiation
= 0.49 mm^-1
T = 298 K
0.49 × 0.45 × 0.27 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.795, T_max = 0.879
5617 measured reflections
2103 independent reflections
1798 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.113
S = 1.04
2103 reflections
136 parameters
H-atom parameters constrained
_max = 0.54 e Å^-3
_min = -0.43 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5-C10 ring.

D-HA	D-H	HA	DA	D-HA
N2-H2AO1	0.86	2.01	2.677 (3)	134
N1-H1AS1ⁱ	0.86	2.53	3.3709 (19)	165
C1-H1CCg1ⁱⁱ	0.97	2.84	3.466	123
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) -x+2, -y+1, -z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2535 ).

Acknowledgements

The authors thank the Ministry of Higher Education of Malaysia for the research grant UKM-OUP-NBT-27-144 and Universiti Kebangsaan Malaysia for the research facilities.

References

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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Ismail, N. L., Othman, E. & Yamin, B. M. (2007). Acta Cryst. E63, o2442-o2443.
Ismail, N. & Yamin, B. M. (2009). X-ray Struct. Anal. Online, 25, 39-40
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds