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Volume 69 
Part 9 
Pages o1374-o1375  
September 2013  

Received 2 July 2013
Accepted 22 July 2013
Online 3 August 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.122
Data-to-parameter ratio = 25.4
Details
Open access

N,N'-Bis(phenylcarbamothioyl)benzene-1,3-dicarboxamide

aDepartment of Chemistry, Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia,bDepartment of Molecular Biology, Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: mustaqim@usm.my

The asymmetric unit of the title compound, C22H18N4O2S2, contains two molecules. In one of them, the dihedral angles between the central benzene ring and the phenyl rings are 16.97 (8) and 20.97 (8)°, while the phenyl rings make a dihedral angle of 37.87 (8)°. In the other molecule, the corresponding values are 34.92 (7), 53.90 (7) and 60.68 (8)°, respectively. In each molecule, two intramolecular N-H...O hydrogen bonds generate S(6) rings and a short C-H...S contact also occurs. In the crystal, N-H...S, N-H...O, C-H...O and C-H...S interactions link the molecules into a three-dimensional network.

Related literature

For biological applications of benzimidazole derivatives, see: Madan et al. (1991[Madan, V. K., Taneja, A. D. & Kudesia, V. P. (1991). J. Indian Chem. Soc. 68, 471-472.]); Fernandez et al. (2005[Fernandez, E. R., Manzano, J. L., Benito, J. J., Hermosa, R., Monte, E. & Criado, J. J. (2005). J. Inorg. Biochem. 99, 1559-1572.]); Kucukguzel et al. (2008[Kucukguzel, I., Tatar, E., Kucukguzel, S. G., Rollas, S. & Clercq, E. D. (2008). Eur. J. Med. Chem. 43, 381-392.]); Saeed et al. (2009[Saeed, A., Abbas, N., Rafique, H., Rashid, S. & Hameed, A. (2009). Chemistry, 18, 152-158.]). For biological properties of thioureas, see: Rauf et al. (2009[Rauf, M. K., Din, I. U., Badshah, A., Geilen, M., Ebihara, M., Vos, D. & Ahmed, S. (2009). J. Inorg. Biochem. 103, 1135-1144.]).

[Scheme 1]

Experimental

Crystal data
  • C22H18N4O2S2

  • Mr = 434.52

  • Triclinic, [P \overline 1]

  • a = 11.1812 (2) Å

  • b = 11.5623 (2) Å

  • c = 16.4471 (2) Å

  • [alpha] = 101.420 (1)°

  • [beta] = 98.127 (1)°

  • [gamma] = 101.316 (1)°

  • V = 2007.43 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.29 mm-1

  • T = 100 K

  • 0.47 × 0.33 × 0.11 mm

Data collection
  • Bruker APEX DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.876, Tmax = 0.968

  • 41276 measured reflections

  • 14580 independent reflections

  • 11642 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.122

  • S = 1.03

  • 14580 reflections

  • 573 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.53 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1A-H1NA...O1A 0.83 (2) 1.976 (19) 2.6722 (16) 140.9 (19)
N2A-H2NA...S2Bi 0.85 (2) 2.59 (2) 3.4201 (12) 165.0 (19)
N3A-H3NA...O2Bii 0.864 (19) 2.31 (2) 2.9715 (15) 133.3 (18)
N4A-H4NA...O2A 0.90 (2) 1.86 (2) 2.6064 (17) 138.2 (18)
N1B-H1NB...O1B 0.86 (2) 1.88 (2) 2.6248 (17) 144.5 (19)
N2B-H2NB...S1Biii 0.834 (19) 2.71 (2) 3.4961 (12) 158.3 (19)
N3B-H3NB...S1Ai 0.84 (2) 2.62 (2) 3.4336 (12) 163.0 (18)
N4B-H4NB...O2B 0.87 (2) 1.92 (2) 2.6543 (16) 141.1 (19)
C5A-H5AA...S1A 0.95 2.51 3.1910 (16) 129
C1B-H1BA...S1B 0.95 2.68 3.2693 (15) 121
C4B-H4BA...O2Aiv 0.95 2.55 3.4819 (18) 165
C10B-H10B...S2Av 0.95 2.84 3.4570 (15) 123
C11B-H11B...S2Av 0.95 2.85 3.4687 (15) 123
C14A-H14A...O2Bii 0.95 2.35 3.2700 (17) 164
C14B-H14B...O1Aii 0.95 2.36 3.2897 (17) 165
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x+1, -y+1, -z; (iii) -x, -y+1, -z; (iv) -x+1, -y+1, -z+1; (v) x-1, y+1, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7103 ).


Acknowledgements

ZN, MAMA and HH thank Universiti Malaysia Sarawak and the Ministry of Science, Technology and Innovation, MOSTI, for financing this project through FRGS/01 (14)/743/2010 (29). WSHWZ thanks Yayasan Tunku Abdul Rahman for providing a scholarship for her postgraduate studies. MMR thanks Universiti Sains Malaysia (USM) for the research facilities and USM Short Term Grant (No. 304/PFIZIK/6312078).

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Fernandez, E. R., Manzano, J. L., Benito, J. J., Hermosa, R., Monte, E. & Criado, J. J. (2005). J. Inorg. Biochem. 99, 1559-1572.
Kucukguzel, I., Tatar, E., Kucukguzel, S. G., Rollas, S. & Clercq, E. D. (2008). Eur. J. Med. Chem. 43, 381-392.  [ISI] [PubMed]
Madan, V. K., Taneja, A. D. & Kudesia, V. P. (1991). J. Indian Chem. Soc. 68, 471-472.  [ChemPort]
Rauf, M. K., Din, I. U., Badshah, A., Geilen, M., Ebihara, M., Vos, D. & Ahmed, S. (2009). J. Inorg. Biochem. 103, 1135-1144.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Saeed, A., Abbas, N., Rafique, H., Rashid, S. & Hameed, A. (2009). Chemistry, 18, 152-158.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1374-o1375   [ doi:10.1107/S1600536813020163 ]

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