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Volume 68 
Part 1 
Pages o94-o95  
January 2012  

Received 21 November 2011
Accepted 6 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.100
Data-to-parameter ratio = 17.8
Details
Open access

2-(5-Fluoro-2,3-dioxoindolin-1-yl)ethyl 4-methylpiperazine-1-carbodithioate

aDepartment of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China
Correspondence e-mail: slcao@cnu.edu.cn

In the title compound, C16H18FN3O2S2, the methylpiperazine ring adopts a chair conformation, while the (2,3-dioxoindolin-1-yl)ethyl unit is linked to one of the N atoms of the piperazine ring via the carbodithioate group. In the crystal, each molecule is linked to its neighbors within the ([\overline{1}]03) plane through weak C-H(methylene)...O, C-H(aryl)...O and C-H(methylene)...S interactions. Perpendicular to this plane molecules are connected through intermolecular short N...[pi](pyrrole ring) contacts [N...C centroid = 3.232 (2) Å], another set of C-H(methylene)...O interactions and through short contacts between carbodithioate S atoms and the pyrrole rings [C...centroid = 3.695 (3), S...centroid = 3.403 (2) Å].

Related literature

For background to indoline-2,3-dione and its derivatives, see: Bhattacharya & Chakrabarti (1998[Bhattacharya, S. K. & Chakrabarti, A. (1998). Indian J. Exp. Biol. 36, 118-121.]); Sridhar & Ramesh (2001[Sridhar, S. K. & Ramesh, A. (2001). Biol. Pharm. Bull. 24, 1149-1152.]); Medvedev et al. (1996[Medvedev, A. E., Clow, A., Sandler, M. & Glover, V. (1996). Biochem. Pharmacol. 52, 385-391.]) and to dithiocarbamates, see: Ozkirimli et al. (2005[Ozkirimli, S., Apak, T. I., Kiraz, M. & Yegenoglu, Y. (2005). Arch. Pharm. Res. 28, 1213-1218.]); Cao et al. (2005[Cao, S. L., Feng, Y. P., Jiang, Y. Y., Liu, S. Y., Ding, G. Y. & Li, R. T. (2005). Bioorg. Med. Chem. Lett. 15, 1915-1917.]); Gaspari et al. (2006[Gaspari, P., Banerjee, T., Malachowski, W. P., Muller, A. J., Prendergast, G. C., DuHadaway, J., Bennett, S. & Donovan, A. M. (2006). J. Med. Chem. 49, 684-692.]). For analogues of 5-fluoroindoline-2,3-dione, see: Wang et al. (2010[Wang, Y., Wan, C.-Q., Cao, S.-L. & Zheng, T. (2010). Acta Cryst. E66, o2243.]). For N...[pi] contacts, see: Black et al. (2007[Black, C. A., Hanton, L. R. & Spicer, M. D. (2007). Inorg. Chem. 46, 3669-3679.]). For van der Waals radii, see Bondi (1964[Bondi, A. (1964). J. Phys. Chem. 68, 441-51.]). For the thickness of phenyl rings, see: Malone et al. (1997[Malone, J. F., Murray, C. M., Charlton, M. H., Docherty, R. & Lavery, A. J. (1997). J Chem. Soc. Faraday Trans. 93, 3429-3436.]). For C=O...[pi] (pyridyl) contacts, see: Wan et al. (2008[Wan, C. Q., Chen, X. D. & Mak, T. C. W. (2008). CrystEngComm, 10, 475-478.])

[Scheme 1]

Experimental

Crystal data
  • C16H18FN3O2S2

  • Mr = 367.45

  • Monoclinic, P 21 /n

  • a = 10.0258 (4) Å

  • b = 15.9925 (6) Å

  • c = 11.0016 (5) Å

  • [beta] = 106.656 (3)°

  • V = 1689.96 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.34 mm-1

  • T = 296 K

  • 0.30 × 0.30 × 0.20 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker 2007[Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.658, Tmax = 0.746

  • 18809 measured reflections

  • 3861 independent reflections

  • 3058 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.100

  • S = 1.04

  • 3861 reflections

  • 217 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 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
C13-H13B...O2i 0.97 2.50 3.225 (2) 131
C12-H12A...O2ii 0.97 2.61 3.385 (2) 137
C15-H15B...O2ii 0.97 2.62 3.383 (2) 136
C1-H1A...O1iii 0.93 2.70 3.282 (3) 121
C2-H2A...O1iii 0.93 2.67 3.275 (2) 124
C12-H12B...S2i 0.97 2.97 3.866 (3) 155
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2007[Bruker (2007). APEX2, SADABS and SAINT. 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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: ZL2432 ).


Acknowledgements

The authors are grateful to the National Natural Science Foundation of China (project No. 20972099) and the Beijing Municipal Commission of Education for financial support.

References

Bhattacharya, S. K. & Chakrabarti, A. (1998). Indian J. Exp. Biol. 36, 118-121.  [ChemPort] [PubMed]
Black, C. A., Hanton, L. R. & Spicer, M. D. (2007). Inorg. Chem. 46, 3669-3679.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Bondi, A. (1964). J. Phys. Chem. 68, 441-51.  [CrossRef] [ChemPort] [ISI]
Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cao, S. L., Feng, Y. P., Jiang, Y. Y., Liu, S. Y., Ding, G. Y. & Li, R. T. (2005). Bioorg. Med. Chem. Lett. 15, 1915-1917.  [CrossRef] [PubMed] [ChemPort]
Gaspari, P., Banerjee, T., Malachowski, W. P., Muller, A. J., Prendergast, G. C., DuHadaway, J., Bennett, S. & Donovan, A. M. (2006). J. Med. Chem. 49, 684-692.  [ISI] [CrossRef] [PubMed] [ChemPort]
Malone, J. F., Murray, C. M., Charlton, M. H., Docherty, R. & Lavery, A. J. (1997). J Chem. Soc. Faraday Trans. 93, 3429-3436.  [CrossRef] [ChemPort]
Medvedev, A. E., Clow, A., Sandler, M. & Glover, V. (1996). Biochem. Pharmacol. 52, 385-391.  [CrossRef] [ChemPort] [PubMed] [ISI]
Ozkirimli, S., Apak, T. I., Kiraz, M. & Yegenoglu, Y. (2005). Arch. Pharm. Res. 28, 1213-1218.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Sridhar, S. K. & Ramesh, A. (2001). Biol. Pharm. Bull. 24, 1149-1152.  [CrossRef] [PubMed] [ChemPort]
Wan, C. Q., Chen, X. D. & Mak, T. C. W. (2008). CrystEngComm, 10, 475-478.  [ISI] [CSD] [CrossRef] [ChemPort]
Wang, Y., Wan, C.-Q., Cao, S.-L. & Zheng, T. (2010). Acta Cryst. E66, o2243.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o94-o95   [ doi:10.1107/S1600536811052494 ]

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