4-(2-Fluoro­phen­yl)-1-(2-oxoindolin-3-yl­idene)thio­semicarbazide

Pervez, H.; Yaqub, M.; Ramzan, M.; Iqbal, M.S.; Tahir, M.N.

doi:10.1107/S1600536810011682

Volume 66
Part 5
Page o1018
May 2010

Received 26 March 2010
Accepted 28 March 2010
Online 2 April 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R = 0.047
wR = 0.114
Data-to-parameter ratio = 13.2
Details

4-(2-Fluorophenyl)-1-(2-oxoindolin-3-ylidene)thiosemicarbazide

Humayun Pervez,^a Muhammad Yaqub,^a Muhammad Ramzan,^a Mohammad S. Iqbal ^b and M. Nawaz Tahir ^c ^*

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan,^bDepartment of Chemistry, Government College University, Lahore, Pakistan, and ^cDepartment of Physics, University of Sargodha, Sargodha, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

The title compound, C₁₅H₁₁FN₄OS, is almost planar, the dihedral angle between the aromatic ring systems being 5.00 (13)°. The conformation is stabilized by intramolecular N-HN and N-HO hydrogen bonds, which generate S(5) and S(6) rings, respectively. N-HF and C-HS interactions also occur. In the crystal, inversion dimers linked by pairs of N-HO hydrogen bonds occur, generating R₂²(8) loops.

Related literature

For related structures and medicinal background, see: Pervez et al. (2009, 2010). For graph-set theory, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₅H₁₁FN₄OS
M_r = 314.34
Monoclinic, P 2₁ /c
a = 5.7646 (3) Å
b = 18.4939 (12) Å
c = 13.6772 (8) Å
= 91.212 (3)°
V = 1457.80 (15) Å³
Z = 4
Mo K radiation
= 0.24 mm^-1
T = 296 K
0.30 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.963, T_max = 0.971
11407 measured reflections
2626 independent reflections
1437 reflections with I > 2(I)
R_int = 0.068

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.114
S = 0.96
2626 reflections
199 parameters
H-atom parameters constrained
_max = 0.15 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.86	2.07	2.912 (3)	164
N3-H3O1	0.86	2.08	2.762 (3)	135
N4-H4AF1	0.86	2.21	2.613 (2)	109
N4-H4AN2	0.86	2.13	2.585 (3)	113
C15-H15S1	0.93	2.56	3.216 (3)	128
Symmetry code: (i) -x+2, -y, -z.

Data collection: APEX2 (Bruker, 2007); cell refinement: 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: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5381 ).

Acknowledgements

HP, MY and MR wish to acknowledge partial financial assistance given by the MoST, Government of Pakistan, under Projects for the Strengthening of S&T Education in Universities (Project No. P&D/S&T/2001/231).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Pervez, H., Manzoor, N., Yaqub, M., Khan, A., Khan, K. M., Nasim, F. H. & Choudhary, M. I. (2010). Lett. Drug Des. Discov. 7, 102-108.
Pervez, H., Yaqub, M., Manzoor, N., Tahir, M. N. & Iqbal, M. S. (2009). Acta Cryst. E65, o2858.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds