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Volume 70 
Part 1 
Pages o64-o65  
January 2014  

Received 11 November 2013
Accepted 9 December 2013
Online 14 December 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.029
wR = 0.084
Data-to-parameter ratio = 15.8
Details
Open access

2-(5-Chloro-2-oxoindolin-3-yl­idene)hydrazinecarbo­thio­amide

aEscola de Quimica e Alimentos, Universidade Federal do Rio Grande, Av. Italia, km 08, Campus Carreiros, 96203-900 Rio Grande-RS, Brazil, and bDepartamento de Quimica, Universidade Federal de Santa Maria, Av. Roraima, Campus, 97105-900 Santa Maria-RS, Brazil
Correspondence e-mail: vanessa.gervini@gmail.com

The title mol­ecule, C9H7ClN4OS, is almost planar, with an r.m.s. deviation of 0.034 (2) Å for the mean plane through all the non-H atoms. Intra­molecular N-H...O and N-H...N hydrogen bonds form S(6) and S(5) ring motifs, respectively. In the crystal, mol­ecules are assembled into inversion dimers through pairs of co-operative N-H...Cl inter­actions. These dimers are connected along the b axis by N-H...O and N-H...S hydrogen bonds, generating layers parallel to (103). The layers are further connected along the a axis into a three-dimensional network, through weak [pi]-[pi] stacking inter­actions [centroid-centroid distance = 3.849 (2) Å].

Related literature

For the synthesis of the title compound, see: Qasem Ali et al. (2011[Qasem Ali, A., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2011). Acta Cryst. E67, o3141-o3142.]). For similar hydrazinecarbo­thio­amide crystal structures, see: Bandeira et al. (2013[Bandeira, K. C. T., Bresolin, L., Näther, C., Jess, I. & Oliveira, A. B. (2013). Acta Cryst. E69, o1251-o1252.]); Ali et al. (2012[Ali, A. Q., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2012). Acta Cryst. E68, o2868-o2869.]); de Oliveira et al. (2012[Oliveira, A. B. de, Silva, C. S., Feitosa, B. R. S., Näther, C. & Jess, I. (2012). Acta Cryst. E68, o2581.]). For the biological activity of isatin and derivatives, see: Cerchiaro & Ferreira (2006[Cerchiaro, G. & Ferreira, A. M. C. (2006). J. Braz. Chem. Soc. 17, 1473-1485.]).

[Scheme 1]

Experimental

Crystal data
  • C9H7ClN4OS

  • Mr = 254.70

  • Monoclinic, P 21 /n

  • a = 5.260 (5) Å

  • b = 15.396 (10) Å

  • c = 13.215 (9) Å

  • [beta] = 96.53 (2)°

  • V = 1063.4 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.54 mm-1

  • T = 173 K

  • 1.27 × 0.38 × 0.35 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.639, Tmax = 0.746

  • 6939 measured reflections

  • 2540 independent reflections

  • 2374 reflections with I > 2[sigma](I)

  • Rint = 0.014

Refinement
  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.084

  • S = 0.81

  • 2540 reflections

  • 161 parameters

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

  • [Delta][rho]max = 0.52 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H21...O1 0.865 (18) 2.127 (18) 2.783 (2) 132.2 (15)
N4-H41...S1i 0.90 (2) 2.47 (2) 3.354 (2) 169.5 (19)
N1-H11...O1ii 0.88 (2) 1.98 (2) 2.848 (2) 169 (2)
N1-H12...N3 0.88 (3) 2.15 (3) 2.594 (2) 110 (2)
N1-H12...Cl1iii 0.88 (3) 2.62 (3) 3.342 (2) 139 (2)
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) -x+2, -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: 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: 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: LR2119 ).


Acknowledgements

We gratefully acknowledge Professor Dr. Manfredo Hörner (Federal University of Santa Maria, Brazil) for his help and support with the X-ray measurements. We also acknowledge financial support through the DECIT/SCTIE-MS-CNPq- FAPERGS-Pronem-# 11/2029-1 and PRONEX-CNPq- FAPERGS projects.

References

Ali, A. Q., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2012). Acta Cryst. E68, o2868-o2869.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Bandeira, K. C. T., Bresolin, L., Näther, C., Jess, I. & Oliveira, A. B. (2013). Acta Cryst. E69, o1251-o1252.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cerchiaro, G. & Ferreira, A. M. C. (2006). J. Braz. Chem. Soc. 17, 1473-1485.  [CrossRef] [ChemPort]
Oliveira, A. B. de, Silva, C. S., Feitosa, B. R. S., Näther, C. & Jess, I. (2012). Acta Cryst. E68, o2581.  [CSD] [CrossRef] [IUCr Journals]
Qasem Ali, A., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2011). Acta Cryst. E67, o3141-o3142.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o64-o65   [ doi:10.1107/S1600536813033369 ]

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