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Volume 69 
Part 12 
Page o1760  
December 2013  

Received 18 October 2013
Accepted 5 November 2013
Online 13 November 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.047
wR = 0.115
Data-to-parameter ratio = 13.0
Details
Open access

A monoclinic polymorph of 1-benzoyl-4-thio­biuret

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

The title compound, C9H9N3O2S, is a monoclinic (C2/c) polymorph of the previously reported triclinic structure [Kang (2013[Kang, S. K. (2013). Acta Cryst. E69, o1327.]). Acta Cryst. E69, o1327]. The mol­ecule is almost planar with an r.m.s. deviation of 0.069 Å from the mean plane of all non-H atoms. The benzoyl and terminal thio­urea fragments adopt a transoid conformation with respect to the central carbonyl O atom. Two intra­molecular N-H...O hydrogen bonds are present. In the crystal, N-H...O and N-H...S inter­actions link the mol­ecules into zigzag chains extending along the c-axis direction.

Related literature

For the biological activity of thia­diazole derivatives, see: Piskala et al. (2004[Piskala, A., Vachalkova, A., Masojidkova, M., Horvathova, K., Ovesna, Z., Paces, V. & Novotny, L. (2004). Parmazie, 59, 756-762.]); Castro et al. (2008[Castro, A., Encinas, A., Gil, C., Brase, S., Porcal, W., Perez, C., Moreno, F. J. & Martinez, A. (2008). Bioorg. Med. Chem. 16, 495-510.]). For the structure and reactivity of thia­diazole derivatives, see: 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 compound, see: Kang et al. (2012[Kang, S. K., Cho, N. S. & Jeon, M. K. (2012). Acta Cryst. E68, o395.]) and of the monoclinic polymorph, see: Kang (2013[Kang, S. K. (2013). Acta Cryst. E69, o1327.]).

[Scheme 1]

Experimental

Crystal data
  • C9H9N3O2S

  • Mr = 223.25

  • Monoclinic, C 2/c

  • a = 14.4259 (14) Å

  • b = 6.6145 (6) Å

  • c = 21.722 (2) Å

  • [beta] = 94.166 (3)°

  • V = 2067.2 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.30 mm-1

  • T = 296 K

  • 0.18 × 0.12 × 0.04 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.96, Tmax = 0.99

  • 7756 measured reflections

  • 1973 independent reflections

  • 1293 reflections with I > 2[sigma](I)

  • Rint = 0.059

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.115

  • S = 1.03

  • 1973 reflections

  • 152 parameters

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

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N9-H9...O11i 0.81 (3) 2.20 (3) 2.945 (3) 151 (2)
N12-H12...O8 0.86 (3) 1.97 (3) 2.661 (3) 136 (2)
N15-H15A...S14ii 0.98 (4) 2.41 (4) 3.358 (3) 163 (3)
N15-H15B...O11 0.81 (3) 2.06 (3) 2.653 (3) 130 (3)
Symmetry codes: (i) [-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (ii) -x+1, -y, -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, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (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.]); 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: LR2116 ).


References

Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Castro, A., Encinas, A., Gil, C., Brase, S., Porcal, W., Perez, C., Moreno, F. J. & Martinez, A. (2008). Bioorg. Med. Chem. 16, 495-510.  [CrossRef] [PubMed] [ChemPort]
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]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Kang, S. K. (2013). Acta Cryst. E69, o1327.  [CSD] [CrossRef] [IUCr Journals]
Kang, S. K., Cho, N. S. & Jeon, M. K. (2012). Acta Cryst. E68, o395.  [CSD] [CrossRef] [IUCr Journals]
Piskala, A., Vachalkova, A., Masojidkova, M., Horvathova, K., Ovesna, Z., Paces, V. & Novotny, L. (2004). Parmazie, 59, 756-762.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1760  [ doi:10.1107/S1600536813030250 ]

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