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

Humayun Pervez; Muhammad Yaqub; Muhammad Ramzan; Mohammad S Iqbal; M Nawaz Tahir

doi:10.1107/S1600536810011682

. 2010 Apr 2;66(Pt 5):o1018. doi: 10.1107/S1600536810011682

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

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

PMCID: PMC2979150 PMID: 21579082

Abstract

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—H⋯N and N—H⋯O hydrogen bonds, which generate S(5) and S(6) rings, respectively. N—H⋯F and C—H⋯S interactions also occur. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds occur, generating R ₂ ²(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,
a = 5.7646 (3) Å
b = 18.4939 (12) Å
c = 13.6772 (8) Å
β = 91.212 (3)°
V = 1457.80 (15) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.068

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.114
S = 0.96
2626 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.22 e Å⁻³

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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011682/hb5381sup1.cif

e-66-o1018-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011682/hb5381Isup2.hkl

e-66-o1018-Isup2.hkl^{(126.3KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.07	2.912 (3)	164
N3—H3⋯O1	0.86	2.08	2.762 (3)	135
N4—H4A⋯F1	0.86	2.21	2.613 (2)	109
N4—H4A⋯N2	0.86	2.13	2.585 (3)	113
C15—H15⋯S1	0.93	2.56	3.216 (3)	128

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Symmetry code: (i) Inline graphic .

Acknowledgments

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).

supplementary crystallographic information

Comment

As part of our ongoing studies of N⁴-arylsubstituted isatins-3-thiosemecarbazones with certain medicinal applications (Pervez et al., 2009, 2010), we now report the synthesis and crystal structure of the title compound (I, Fig. 1).

The crystal structure of (II) i.e. 1-(5-nitro-2-oxoindolino-3-ylidene)- 4-o-tolylthiosemicarbazide methanol monosolvate (Pervez et al., 2009) has been published. The title compound (I) differs from (II) due to the absence of nitro function at position-5 of the isatin scaffold and presence of fluoro instead of methyl group at position-2 of the phenyl ring substituted at N⁴ of the thiosemicarbazone moiety. In (I), the 2-oxoindolin A (C1–C8/N1/O1), thiosemicarbazide B (N2/N3/C9/S1/N4) and the 2-fluorophenyl C (C10—C15/F1) are planar with maximum r. m. s. deviations of 0.0289, 0.0261 and 0.0056 Å, respectively. Due to intramolecular H-bondings (Table 1, Fig. 1), two S(5) and two S(6) (Bernstein et al., 1995) ring motifs are formed. The molecules are dimerised due to intermolecular H-bonding of N—H···O type with R₂²(8) ring motifs.

Experimental

To a hot solution of isatin (0.74 g, 5.0 mmol) in ethanol (10 ml) containing a few drops of glacial acetic acid was added 4-o -fluorophenylthiosemicarbazide (0.93 g, 5.0 mmol) dissolved in ethanol (10 ml) under stirring. The reaction mixture was then heated under reflux for 2 h. The yellow crystalline solid formed during refluxing was collected by suction filtration. Thorough washing with hot ethanol followed by ether furnished the target compound (I) in pure form (1.20 g, 76 %), m.p. 505-507 K (d). The dark yellow needles of (I) were grown in ethyl acetate-petroleum ether (1:5) system by diffusion method at room temperature.