Crystal structure of 3-[(E)-2-(4-phenyl-1,3-thia­zol-2-yl)hydrazin-1-yl­idene]indolin-2-one

Bhimashankar M Halasangi; Prema S Badami; Sangamesh A Patil; G N Anil Kumar

doi:10.1107/S1600536814022715

. 2014 Oct 24;70(Pt 11):o1177–o1178. doi: 10.1107/S1600536814022715

Crystal structure of 3-[(E)-2-(4-phenyl-1,3-thiazol-2-yl)hydrazin-1-ylidene]indolin-2-one

Bhimashankar M Halasangi ^a, Prema S Badami ^b, Sangamesh A Patil ^a, G N Anil Kumar ^c,^*

PMCID: PMC4257251 PMID: 25484816

Abstract

In the title molecule, C₁₇H₁₂N₄OS, the thiazole ring forms a dihedral angle of 10.8 (2)° with the phenyl ring and an angle of 3.1 (3)° with the indole ring system [which has a maximum deviation of 0.035 (2) Å]. The dihedral angle between the planes of the phenyl ring and the indole ring system is 11.5 (1)°. An intramolecular N—H⋯O hydrogen bond is observed. In the crystal, pairs of N—H⋯O hydrogen bonds form inversion dimers with an R ² ₂(8) graph-set motif.

Keywords: crystal structure; indolinone; hydrazine; 1,3-thiazole; hydrogen bonding; biological activity

Related literature

For the biological activities of substituted thiazoles, see: Ali et al. (2011 ▶); Bharti et al. (2010 ▶); Kondratieva et al. (2007 ▶). For a related structure, see: Sadık et al. (2004 ▶).

Experimental

Crystal data

C₁₇H₁₂N₄OS
M _r = 320.37
Monoclinic,
a = 17.7108 (8) Å
b = 5.1411 (2) Å
c = 15.9065 (6) Å
β = 94.706 (3)°
V = 1443.45 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.35 × 0.31 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.887, T _max = 0.934
11530 measured reflections
3142 independent reflections
2124 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.109
S = 1.09
3142 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814022715/lh5732sup1.cif

e-70-o1177-sup1.cif^{(21.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814022715/lh5732Isup2.hkl

e-70-o1177-Isup2.hkl^{(151.1KB, hkl)}

Click here for additional data file.^{(5.9KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814022715/lh5732Isup3.cml

Click here for additional data file.^{(263.7KB, tif)}

. DOI: 10.1107/S1600536814022715/lh5732fig1.tif

The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. The dashed line indicates an intramolecular N—H⋯N bond

Click here for additional data file.^{(551.7KB, tif)}

. DOI: 10.1107/S1600536814022715/lh5732fig2.tif

Part of the crystal structure with hydrogen bonds indicated as dotted lines

CCDC reference: 1029498

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
N2H2O1	0.86	2.12	2.771(2)	133
N4H4O1ⁱ	0.86	2.11	2.922(2)	158

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Symmetry code: (i) Inline graphic .

Acknowledgments

USIC, Karnatak University, Dharwad, is greatly acknowledged for the single-crystal XRD data collection. BMH is grateful to the UGC for financial support in the form of an RFSMS scholarship.

supplementary crystallographic information

S1. Experimental

S1.1. Synthesis and crystallization

An ethanolic solution of 1.81g (0.01 M) of 2-hydrazino-4-phenylthiazole was added drop wise to an etanolic solution of 1.47g (0.01 M) of isatin with constant stirring. After the complete addition, the reaction mixture was stirred further for 8-9 hrs until the solid separated out from the reaction mixture. The separated solid was filtered and washed with cold alcohol, dried and recrystallized from DMF (Yield: 95 %. MP: 443-446K). Block-shaped colourless crystals were obtained by slow evaporation of a solution of the title compound at room temperature in DMF:water in the ratio 2:1.

S1.2. Refinement

H atoms were placed in idealized positions and refined using a riding-model approximation with N—H = 0.86 Å, C—H = 0.93 Å and with U_iso(H) = 1.2U_eq(N,C).

S2. Comment

Isatin derivatives and compounds containing a thiazole ring are class of organic compounds which have fascinated many synthetic researchers due to their wide range of biological activity ( Ali et al., 2011; Bharti et al., 2010; Kondratieva et al., 2007).

The molecular structure of the title compound is shown in Fig. 1. An intramolecular N—H···O hydrogen bond is observed. The thiazole ring is essentially planar with a maximum deviation of 0.005 (2) Å for atom N1. The thiazole ring (S1/C9/N1/C7/C8) forms dihedral angles of 10.8 (2)° with the phenyl ring (C1–C6) and 3.1 (3)° with the indole ring system (C10—C16/N4/C17, with a maximum deviation of 0.035 (2)Å for atom C17). The dihedral angle between the phenyl ring and the indole ring system is 11.5 (1)Å. In the crystal, pairs of N—H···O hydrogen bonds form inversion dimers (Fig. 2). A closely related structure appears in the literature (Sadik, et al., 2004).