Ethyl 2-[3-(3,5-Dinitrobenzo­yl)thio­ureido]benzoate

Saeed, S.; Rashid, N.; Bhatti, M.H.; Wong, W.-T.

doi:10.1107/S1600536811012918

Volume 67
Part 5
Page o1114
May 2011

Received 14 March 2011
Accepted 6 April 2011
Online 13 April 2011

Key indicators
Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R = 0.037
wR = 0.095
Data-to-parameter ratio = 10.0
Details

Ethyl 2-[3-(3,5-Dinitrobenzoyl)thioureido]benzoate

Sohail Saeed,^a ^* Naghmana Rashid,^a Moazzam H. Bhatti ^a and Wing-Tak Wong ^b

^aDepartment of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad 44000, Pakistan, and ^bDepartment of Chemistry, The University of Hong Kong, Pokfulam Road, Pokfulam, Hong Kong SAR, People's Republic of China
Correspondence e-mail: Sohail262001@yahoo.com

In the title compound, C₁₇H₁₄N₄O₇S, the dihedral angle between the two benzene rings is 9.04 (15)°. The centroid-centroid distance of 3.9825 (19) Å between nearly parallel benzene rings of adjacent molecules suggests the existence of [pi] - [pi] stacking. Intermolecular and intra-molecular N-HO hydrogen bonding is present in the structure. The ethoxy group is disordered over two sets of sites with an occupancy ratio of 0.580 (15):0.420 (15). The crystal studied was an inversion twin.

Related literature

For background to the chemistry of thiourea derivatives and their bioloical activity, and a related structure, see: Saeed et al. (2010).

Experimental

Crystal data

C₁₇H₁₄N₄O₇S
M_r = 418.38
Monoclinic, C c
a = 11.7264 (19) Å
b = 16.617 (3) Å
c = 9.9630 (16) Å
= 101.522 (2)°
V = 1902.3 (5) Å³
Z = 4
Mo K radiation
= 0.22 mm^-1
T = 299 K
0.27 × 0.16 × 0.08 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) T_min = 0.943, T_max = 0.983
4944 measured reflections
3011 independent reflections
2727 reflections with I > 2(I)
R_int = 0.014

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.095
S = 1.10
3011 reflections
301 parameters
42 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.22 e Å^-3
_min = -0.24 e Å^-3
Absolute structure: Flack (1983), 1340 Friedel pairs
Flack parameter: 0.39 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O2	0.91 (3)	1.95 (3)	2.672 (3)	134 (2)
N1-H1O3	0.91 (3)	2.01 (3)	2.700 (3)	131 (2)
N2-H2O3ⁱ	0.77 (3)	2.32 (3)	3.086 (3)	172 (2)
Symmetry code: (i) $[x, -y, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5177 ).

Acknowledgements

The authors are grateful to Allama Iqbal Open University, Islamabad, Pakistan, for the allocation of research and analytical laboratory facilities.

References

Bruker. (1998). SMART, Madison, Wisconsin, USA.
Bruker. (2006). SAINT, Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Saeed, S., Rashid, N. & Wong, W.-T. (2010). Acta Cryst. E66, o980.
Sheldrick, G. M. (2004). SADABS, University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds