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Volume 69 
Part 8 
Page o1327  
August 2013  

Received 16 July 2013
Accepted 19 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.037
wR = 0.097
Data-to-parameter ratio = 16.6
Details
Open access

1-Benzoyl-4-thiobiuret

aDepartment of Chemistry, Chungnam National University, Daejeon 305-764, Republic of Korea
Correspondence e-mail: skkang@cnu.ac.kr

In the title compound (systematic name: {[(phenylformamido)carbonyl]amino}methanethioamide), C9H9N3O2S, both benzoyl and terminal thiourea fragments adopt transoid conformations with respect to the central carbonyl O atom. The benzoyl and thiobiuret groups are almost coplanar, making a dihedral angle of 4.40 (8)°. The molecular structure is stabilized by two intramolecular N-H...O hydrogen bonds. In the crystal, N-H...O and N-H...S hydrogen bonds link the molecules into a tape running along [101].

Related literature

For the structure and reactivity of thiadiazole derivatives, see: Cho, Ra et al. (1996[Cho, N. S., Ra, C. S., Ra, D. Y., Song, J. S. & Kang, S. K. (1996). J. Heterocycl. Chem. 33, 1201-1206.]); Cho, Cho et al. (1996[Cho, N. S., Cho, J. J., Ra, D. Y., Moon, J. H., Song, J. S. & Kang, S. K. (1996). Bull. Korean Chem. Soc. 17, 1170-1174.]). For the structure of a thiobiuret isomer, see: Kang et al. (2012[Kang, S. K., Cho, N. S. & Jeon, M. K. (2012). Acta Cryst. E68, o395.]).

[Scheme 1]

Experimental

Crystal data
  • C9H9N3O2S

  • Mr = 223.25

  • Triclinic, [P \overline 1]

  • a = 5.6616 (1) Å

  • b = 7.8407 (2) Å

  • c = 11.7631 (3) Å

  • [alpha] = 97.169 (2)°

  • [beta] = 94.992 (3)°

  • [gamma] = 101.390 (2)°

  • V = 504.53 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.30 mm-1

  • T = 296 K

  • 0.2 × 0.15 × 0.07 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.94, Tmax = 0.97

  • 17356 measured reflections

  • 2516 independent reflections

  • 1485 reflections with I > 2[sigma](I)

  • Rint = 0.055

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.097

  • S = 0.87

  • 2516 reflections

  • 152 parameters

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

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N9-H9...O11i 0.843 (18) 2.172 (18) 2.9891 (18) 163.3 (16)
N12-H12...O8 0.882 (19) 1.919 (19) 2.6171 (17) 135.0 (17)
N15-H15A...O11 0.91 (2) 1.99 (2) 2.684 (2) 132.0 (17)
N15-H15B...S14ii 0.85 (2) 2.58 (2) 3.4295 (17) 171.3 (17)
Symmetry codes: (i) -x-1, -y+1, -z; (ii) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2002[Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2013[Sheldrick, G. M. (2013). University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013[Sheldrick, G. M. (2013). University of Göttingen, Germany.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5292 ).


References

Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Cho, N. S., Cho, J. J., Ra, D. Y., Moon, J. H., Song, J. S. & Kang, S. K. (1996). Bull. Korean Chem. Soc. 17, 1170-1174.  [ChemPort]
Cho, N. S., Ra, C. S., Ra, D. Y., Song, J. S. & Kang, S. K. (1996). J. Heterocycl. Chem. 33, 1201-1206.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Kang, S. K., Cho, N. S. & Jeon, M. K. (2012). Acta Cryst. E68, o395.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2013). University of Göttingen, Germany.


Acta Cryst (2013). E69, o1327  [ doi:10.1107/S1600536813019983 ]

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