1,5-Bis(2-oxoindolin-3-yl­idene)thio­carbonohydrazide tetra­hydro­furan monosolvate

Shaghayegh Pezeshkpour; Hamid Khaledi; Hapipah Mohd Ali

doi:10.1107/S1600536812022714

. 2012 May 23;68(Pt 6):o1870. doi: 10.1107/S1600536812022714

1,5-Bis(2-oxoindolin-3-ylidene)thiocarbonohydrazide tetrahydrofuran monosolvate

Shaghayegh Pezeshkpour ^a, Hamid Khaledi ^a,^*, Hapipah Mohd Ali ^a

PMCID: PMC3379434 PMID: 22719632

Abstract

In the thiocarbonohydrazide molecule of the title compound, C₁₇H₁₂N₆O₂S·C₄H₈O, the terminal indolin-2-one ring systems make a dihedral angle of 20.13 (6)° with each other. Two intramolecular N—H⋯O hydrogen bonds are present, each of which generates an S(6) ring. In the crystal, N—H⋯O hydrogen bonds lead to a molecular chain running along the b axis. The tetrahydrofuran solvent molecule is disordered over two orientations in a 0.561 (11):0.439 (11) ratio.

Related literature

For the structures of the N-methylisatin analogue and its Sn(IV) complex and also the spectroscopic characterization of the title thiocarbonohydrazide, see: Bacchi et al. (2005 ▶). graphic file with name e-68-o1870-scheme1.jpg

Experimental

Crystal data

C₁₇H₁₂N₆O₂S·C₄H₈O
M _r = 436.49
Triclinic,
a = 8.4768 (1) Å
b = 11.4765 (2) Å
c = 11.9091 (2) Å
α = 75.206 (1)°
β = 72.553 (1)°
γ = 69.416 (1)°
V = 1020.02 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 296 K
0.33 × 0.25 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.938, T _max = 0.975
9421 measured reflections
4451 independent reflections
3628 reflections with I > 2σ(I)
R _int = 0.016

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.121
S = 1.05
4451 reflections
338 parameters
30 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.28 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022714/is5142sup1.cif

e-68-o1870-sup1.cif^{(29.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022714/is5142Isup2.hkl

e-68-o1870-Isup2.hkl^{(218KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812022714/is5142Isup3.cml

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⋯O3ⁱ	0.88 (1)	1.96 (2)	2.829 (15)	168 (2)
N1—H1⋯O3′ⁱ	0.88 (1)	1.98 (3)	2.84 (2)	167 (2)
N3—H3⋯O1	0.85 (1)	2.18 (2)	2.8369 (16)	134 (2)
N4—H4⋯O2	0.86 (1)	2.10 (2)	2.7857 (16)	136 (2)
N6—H6⋯O1ⁱⁱ	0.84 (1)	2.32 (2)	3.0522 (16)	146 (2)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

We thank the University of Malaya for funding this study (ERGS grant No. ER009–2011 A).

supplementary crystallographic information

Comment

Recently, a series of isatin-based thiocarbonohydrazides and the related Sn(IV) complexes were synthesized and studied for their antimicrobial and mutagenic properties (Bacchi et al., 2005). The title compound, being among those, was re-synthesized and grown as X-ray quality crystals from THF by our research group. In the crystal structure, the hydrazone molecule is roughly planar with the maximum deviation from the least-squares plane of all non-H atoms being 0.481 (2) Å for atom C14. The configurations around the C—N bonds, stabilized by intramolecular N—H···O hydrogen bonding (Table 1), are same as those observed in the N-methylisatin analogous. The hydrazone molecule is co-crystallized with one molecule of THF which suffers from disorder. The crystal packing contains chains along the b axis formed by intermolecular N6—H6···O1 hydrogen bonds (Table 1 and Fig. 2). The THF molecules are N—H···O bonded to the chain.

Experimental

The Schiff base was prepared as described previously (Bacchi et al., 2005) and grown as X-ray quality crystals from a THF solution at room temperature.