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Volume 69 
Part 9 
Page o1368  
September 2013  

Received 28 July 2013
Accepted 29 July 2013
Online 3 August 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.050
wR = 0.142
Data-to-parameter ratio = 18.2
Details
Open access

1-[3-({[Bis(2-methylpropyl)carbamothioyl]amino}carbonyl)benzoyl]-3,3-bis(2-methylpropyl)thiourea

aDepartment of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, India,bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: edward.tiekink@gmail.com

The title compound, C26H42N4O2S2, adopts a shallow U-shape as both pendant arms of the 1,3-substituted benzene ring are orientated in the same direction. The thione S atoms lie to the same side of the benzene ring and the carbonyl O atoms to the other. The most prominent feature of the crystal packing is the formation of inversion dimers mediated by N-H...S hydrogen bonds. One of the 2-methylpropyl groups is statistically disordered over two positions.

Related literature

For the use of the title compound in the synthesis of metal macrocycles, see: Nguyen et al. (2011[Nguyen, H. H., Thang, P. C., Rodenstein, A., Kirmse, R. & Abram, U. (2011). Inorg. Chem. 50, 590-596.]). For the structure of the methanol solvate, see: Rodenstein et al. (2007[Rodenstein, A., Richter, R. & Kirmse, R. (2007). Z. Anorg. Allg. Chem. 633, 1713-1717.]).

[Scheme 1]

Experimental

Crystal data
  • C26H42N4O2S2

  • Mr = 506.76

  • Monoclinic, P 21 /c

  • a = 12.6926 (2) Å

  • b = 11.8015 (2) Å

  • c = 19.9701 (4) Å

  • [beta] = 103.883 (2)°

  • V = 2903.97 (9) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 1.87 mm-1

  • T = 100 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]) Tmin = 0.217, Tmax = 1.000

  • 11629 measured reflections

  • 5743 independent reflections

  • 5234 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.142

  • S = 1.01

  • 5743 reflections

  • 316 parameters

  • 30 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.89 e Å-3

  • [Delta][rho]min = -0.82 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...S2i 0.88 2.62 3.4745 (17) 163
N3-H3...S2i 0.88 2.54 3.3870 (18) 162
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5336 ).


Acknowledgements

NS thanks NITT for a Fellowship. The authors also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

References

Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Nguyen, H. H., Thang, P. C., Rodenstein, A., Kirmse, R. & Abram, U. (2011). Inorg. Chem. 50, 590-596.  [ISI] [CSD] [CrossRef] [ChemPort]
Rodenstein, A., Richter, R. & Kirmse, R. (2007). Z. Anorg. Allg. Chem. 633, 1713-1717.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1368  [ doi:10.1107/S1600536813021053 ]

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