Propyl 2-(3-benzoyl­thio­ureido)acetate

Hassan, I.N.; Yamin, B.M.; Kassim, M.B.

doi:10.1107/S1600536808030596

Volume 64
Part 11
Page o2083
November 2008

Received 19 September 2008
Accepted 23 September 2008
Online 9 October 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.068
wR = 0.162
Data-to-parameter ratio = 14.7
Details

Propyl 2-(3-benzoylthioureido)acetate

Ibrahim N. Hassan,^a Bohari M. Yamin ^a and Mohammad B. Kassim ^a ^*

^aSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, UKM 43600 Bangi Selangor, Malaysia
Correspondence e-mail: mbkassim@ukm.my

The title compound, C₁₃H₁₆N₂O₃S, is a thiourea derivative with benzoyl and propoxycarbonylmethyl groups attached to the two terminal N atoms. These groups adopt trans and cis configurations, respectively, with respect to the S atom across the thiourea C-N bonds. The compound crystallizes in the P2₁/c space group with Z = 8, resulting in two unique molecules in the asymmetric unit linked by C-HS and C-HO hydrogen bonds, forming a one-dimensional zigzag chain along the c axis.

Related literature

For information on bond lengths and angles, see: Allen et al. (1987). For related literature on an analogous molecule, see: Hassan et al. (2008). For related structures, see: Yamin & Hassan (2004); Yamin & Yusof (2003).

Experimental

Crystal data

C₁₃H₁₆N₂O₃S
M_r = 280.34
Monoclinic, P 2₁ /c
a = 11.6722 (19) Å
b = 15.105 (3) Å
c = 16.584 (3) Å
= 104.737 (3)°
V = 2827.6 (8) Å³
Z = 8
Mo K radiation
= 0.23 mm^-1
T = 298 (2) K
0.34 × 0.29 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.925, T_max = 0.979
15002 measured reflections
5262 independent reflections
2854 reflections with I > 2(I)
R_int = 0.045

Refinement

R[F² > 2(F²)] = 0.068
wR(F²) = 0.162
S = 1.05
5262 reflections
359 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.21 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2BO1	0.87 (2)	1.92 (2)	2.617 (3)	136 (2)
N2-H2BO2	0.87 (2)	2.33 (2)	2.663 (4)	103.1 (17)
N4-H4BO4	0.87 (3)	1.97 (2)	2.605 (4)	129 (3)
N4-H4BO5	0.87 (3)	2.23 (3)	2.671 (4)	111 (2)
C5-H5AS2	0.93	2.84	3.396 (3)	120
C13-H13BO4ⁱ	0.96	2.54	3.329 (6)	139
C14-H14AS1	0.93	2.78	3.397 (3)	125
C24-H24AO2ⁱⁱ	0.97	2.57	3.441 (4)	150
C26-H26BO1ⁱⁱ	0.96	2.57	3.384 (4)	143
Symmetry codes: (i) x, y, z-1; (ii) x, y, z+1.

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, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2635 ).

Acknowledgements

The authors thank Universiti Kebangsaan Malaysia for providing facilities, and the Ministry of Science, Technology and Innovation for research fund No. UKM-ST-01FRGS0016-2006.

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.
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Hassan, I. N., Yamin, B. M. & Kassim, M. B. (2008). Acta Cryst. E64, o1727.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Yamin, B. M. & Hassan, I. N. (2004). Acta Cryst. E60, o2513-o2514.
Yamin, B. M. & Yusof, M. S. M. (2003). Acta Cryst. E59, o151-o152.

organic compounds