(IUCr) 1,2-Bis[N'-(2,2-dimethylpropionyl)thioureido]cyclohexane

Volume 64
Part 5
Page o937
May 2008

Received 20 April 2008
Accepted 22 April 2008
Online 30 April 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R = 0.045
wR = 0.124
Data-to-parameter ratio = 15.7
Details

1,2-Bis[N'-(2,2-dimethylpropionyl)thioureido]cyclohexane

M. Sukeri M. Yusof,^a ^* Noor Adila C. Ayob,^a Maisara A. Kadir ^b and Bohari M. Yamin ^b

^aDepartment of Chemical Sciences, Faculty of Science and Technology, Universiti Malaysia Terengganu, Mengabang Telipot, 21030 Kuala Terengganu, Malaysia, and ^bSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia
Correspondence e-mail: mohdsukeri@umt.edu.my

In the title compound, C₁₈H₃₂N₄O₂S₂, the dihedral angle between the two thiourea groups is 78.55 (7)°. The molecular conformation is stabilized by intramolecular N-HO hydrogen bonds and the crystal structure is stabilized by intermolecular N-HO and C-HO hydrogen bonds, forming centrosymmetric dimers.

Related literature

For related crystal structures, see: Thiam et al. (2008). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₈H₃₂N₄O₂S₂
M_r = 400.60
Monoclinic, P 2₁ /c
a = 10.960 (2) Å
b = 19.065 (4) Å
c = 10.378 (2) Å
= 96.112 (4)°
V = 2156.1 (8) Å³
Z = 4
Mo K radiation
= 0.27 mm^-1
T = 298 (2) K
0.48 × 0.41 × 0.37 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.883, T_max = 0.908
10928 measured reflections
3779 independent reflections
2828 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.124
S = 1.07
3779 reflections
241 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O1	0.86	1.97	2.650 (2)	135
N3-H3O2	0.86	1.99	2.670 (2)	135
N1-H1O2ⁱ	0.86	2.25	3.078 (2)	161
C1-H1BO2ⁱ	0.96	2.54	3.462 (3)	161
Symmetry code: (i) -x, -y, -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, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2701 ).

Acknowledgements

The authors thank the Malaysian Government, Universiti Kebangsaan Malaysia, Universiti Malaysia Terengganu and the Ministry of Higher Education, Malaysia, for research grants OUP UKM OUP-BIT-28/20076 and UMT-FRGS-59001.

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.
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.
Thiam, E. I., Diop, M., Gaye, M., Sall, A. S. & Barry, A. H. (2008). Acta Cryst. E64, o776.

organic compounds