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

Wang, Y.; Lin, H.-H.; Cao, S.-L.

doi:10.1107/S1600536811052494

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 (C-C) = 0.002 Å
R = 0.035
wR = 0.100
Data-to-parameter ratio = 17.8
Details

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

Yao Wang,^a Hui-Hui Lin ^a and Sheng-Li Cao ^a ^*

^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 [NC 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 [Ccentroid = 3.695 (3), Scentroid = 3.403 (2) Å].

Related literature

For background to indoline-2,3-dione and its derivatives, see: Bhattacharya & Chakrabarti (1998); Sridhar & Ramesh (2001); Medvedev et al. (1996) and to dithiocarbamates, see: Ozkirimli et al. (2005); Cao et al. (2005); Gaspari et al. (2006). For analogues of 5-fluoroindoline-2,3-dione, see: Wang et al. (2010). For N [pi] contacts, see: Black et al. (2007). For van der Waals radii, see Bondi (1964). For the thickness of phenyl rings, see: Malone et al. (1997). For C=O [pi] (pyridyl) contacts, see: Wan et al. (2008)

Experimental

Crystal data

C₁₆H₁₈FN₃O₂S₂
M_r = 367.45
Monoclinic, P 2₁ /n
a = 10.0258 (4) Å
b = 15.9925 (6) Å
c = 11.0016 (5) Å
= 106.656 (3)°
V = 1689.96 (12) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.658, T_max = 0.746
18809 measured reflections
3861 independent reflections
3058 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.100
S = 1.04
3861 reflections
217 parameters
H-atom parameters constrained
_max = 0.22 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C13-H13BO2ⁱ	0.97	2.50	3.225 (2)	131
C12-H12AO2ⁱⁱ	0.97	2.61	3.385 (2)	137
C15-H15BO2ⁱⁱ	0.97	2.62	3.383 (2)	136
C1-H1AO1ⁱⁱⁱ	0.93	2.70	3.282 (3)	121
C2-H2AO1ⁱⁱⁱ	0.93	2.67	3.275 (2)	124
C12-H12BS2ⁱ	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); cell refinement: APEX2 and SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

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

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organic compounds