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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 [sigma](C-C) = 0.005 Å
R = 0.068
wR = 0.162
Data-to-parameter ratio = 14.7
Details
Open access

Propyl 2-(3-benzoylthioureido)acetate

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-H...S and C-H...O 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[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 related literature on an analogous molecule, see: Hassan et al. (2008[Hassan, I. N., Yamin, B. M. & Kassim, M. B. (2008). Acta Cryst. E64, o1727.]). For related structures, see: Yamin & Hassan (2004[Yamin, B. M. & Hassan, I. N. (2004). Acta Cryst. E60, o2513-o2514.]); Yamin & Yusof (2003[Yamin, B. M. & Yusof, M. S. M. (2003). Acta Cryst. E59, o151-o152.]).

[Scheme 1]

Experimental

Crystal data
  • C13H16N2O3S

  • Mr = 280.34

  • Monoclinic, P 21 /c

  • a = 11.6722 (19) Å

  • b = 15.105 (3) Å

  • c = 16.584 (3) Å

  • [beta] = 104.737 (3)°

  • V = 2827.6 (8) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.925, Tmax = 0.979

  • 15002 measured reflections

  • 5262 independent reflections

  • 2854 reflections with I > 2[sigma](I)

  • Rint = 0.045

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2B...O1 0.87 (2) 1.92 (2) 2.617 (3) 136 (2)
N2-H2B...O2 0.87 (2) 2.33 (2) 2.663 (4) 103.1 (17)
N4-H4B...O4 0.87 (3) 1.97 (2) 2.605 (4) 129 (3)
N4-H4B...O5 0.87 (3) 2.23 (3) 2.671 (4) 111 (2)
C5-H5A...S2 0.93 2.84 3.396 (3) 120
C13-H13B...O4i 0.96 2.54 3.329 (6) 139
C14-H14A...S1 0.93 2.78 3.397 (3) 125
C24-H24A...O2ii 0.97 2.57 3.441 (4) 150
C26-H26B...O1ii 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[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).


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.  [CSD] [CrossRef] [details]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.  [ISI] [CrossRef] [ChemPort] [details]
Yamin, B. M. & Hassan, I. N. (2004). Acta Cryst. E60, o2513-o2514.  [CSD] [CrossRef] [details]
Yamin, B. M. & Yusof, M. S. M. (2003). Acta Cryst. E59, o151-o152.  [CrossRef] [details]


Acta Cryst (2008). E64, o2083  [ doi:10.1107/S1600536808030596 ]

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