5-Chloro-N-{4-oxo-2-[4-(trifluoro­meth­yl)phen­yl]-1,3-thia­zolidin-3-yl}-3-phenyl-1H-indole-2-carboxamide

Mehmet Akkurt; İsmail Çelik; Füsun Kazan Gürbüzel; Sumru Özkırımlı; Orhan Büyükgüngör

doi:10.1107/S1600536812039347

. 2012 Sep 22;68(Pt 10):o2969–o2970. doi: 10.1107/S1600536812039347

5-Chloro-N-{4-oxo-2-[4-(trifluoromethyl)phenyl]-1,3-thiazolidin-3-yl}-3-phenyl-1H-indole-2-carboxamide

Mehmet Akkurt ^a,^*, İsmail Çelik ^b, Füsun Kazan Gürbüzel ^c, Sumru Özkırımlı ^c, Orhan Büyükgüngör ^d

PMCID: PMC3470337 PMID: 23125750

Abstract

In the title compound, C₂₅H₁₇ClF₃N₃O₂S, the five-membered 1,3-thiazolidine ring adopts a twist conformation. The three F atoms of the CF₃ group are disordered over two sets of sites with refined occupancies of 0.542 (18) and 0.458 (18). In the nine-membered 1H-indoline ring system, the 1H-pyrrole ring forms a dihedral angle of 4.7 (2)° with the benzene ring, while it is twisted at an angle of 46.5 (2)° with respect to the attached phenyl ring. The dihedral angle between the phenyl and trifluoromethyl-substituted benzene rings is 56.0 (2)°. In the crystal, N—H⋯O hydrogen bonds connect the molecules into a three-dimensional network. In addition, weak C—H⋯O hydrogen bonds and weak C—H⋯π interactions are observed.

Related literature

For medicinal applications of indole derivatives, see: Beale (2011 ▶); Brancale & Silvestri (2007 ▶); Cihan-Ustundag & Capan (2012 ▶); Oudard et al. (2011 ▶); Verma & Saraf (2008 ▶). For the definition of ring-puckering parameters, see: Cremer & Pople (1975 ▶). For related structures, see: Akkurt et al. (2010 ▶, 2011a ▶,b ▶,c ▶). For standard values of bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₅H₁₇ClF₃N₃O₂S
M _r = 515.94
Tetragonal,
a = 22.9020 (6) Å
c = 18.3260 (6) Å
V = 9612.0 (6) Å³
Z = 16
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 296 K
0.57 × 0.43 × 0.29 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.849, T _max = 0.919
71781 measured reflections
4968 independent reflections
3054 reflections with I > 2σ(I)
R _int = 0.076

Refinement

R[F ² > 2σ(F ²)] = 0.073
wR(F ²) = 0.210
S = 1.05
4968 reflections
345 parameters
14 restraints
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039347/lh5532sup1.cif

e-68-o2969-sup1.cif^{(33.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039347/lh5532Isup2.hkl

e-68-o2969-Isup2.hkl^{(243.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812039347/lh5532Isup3.cml

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

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

Cg1 and Cg2 are the centroids of the N1/C1/C6–C8 and C9–C14 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.08	2.864 (4)	151
N2—H2A⋯O2ⁱⁱ	0.86	2.34	2.851 (4)	118
C18—H18⋯O2ⁱⁱ	0.98	2.53	3.145 (5)	121
C24—H24⋯Cg1ⁱⁱⁱ	0.93	2.77	3.438 (5)	129
C17—H17B⋯Cg2^iv	0.97	2.95	3.799 (5)	147

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

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS2 diffractometer (purchased under grant F.279 of the University Research Fund). This work was supported by the Istanbul University Department of Scientific Research Projects (project No T-721/30062005).

supplementary crystallographic information

Comment

The indole ring system is one of the most encountered heterocyles in natural and synthetic drug compounds (Brancale & Silvestri, 2007). Several indole derivatives, such as sunitinib as tyrosine kinase inhibitor (Oudard et al., 2011) or delavirdine as nonnucleoside reverse transcriptase inhibitor (Beale, 2011), are in clinical use. Here, we aimed to combine this basic scaffold with 4-thiazolidinones, which have been shown to have anticancer (Cihan-Ustundag & Capan, 2012), antifungal, antibacterial and antiviral properties (Verma & Saraf, 2008), to obtain leads toward the design of anticancer compounds.

The molecular structure of the title compound is shown in Fig. 1. The 1,3-thiazolidine ring (S1/N3/C16–C18) has a twist conformation as indicated by the puckering parameters (Cremer & Pople, 1975) of Q(2) = 0.354 (4) Å, φ(2) = 342.0 (6)°. In the nine-membered 1H-indoline ring system (N1/C1–C8), the 1H-pyrrole ring (N1C1/C6–C8) makes a dihedral angle of 4.7 (2)° with the benzene ring (C1–C6), while it is twisted an angle of 46.5 (2)° with respect to the attached phenyl ring (C9–C14). The dihedral angle between the C9–C14 phenyl and C19–C24 benzene rings which are attached to the H-pyrrole and 1,3-thiazolidine rings, respectively, is 56.0 (2)°.

All bond lengths and bond angles in (I) are within normal ranges (Allen et al., 1987) and are comparable to those reported for the related structures (Akkurt et al., 2010, 2011a,b,c). The C7—C15—N2—N3, N1—C7—C15—O1 and O1—C15—N2—N3 torsion angles are 176.4 (3), -19.5 (5) and -2.6 (5)°, respectively.

In the crystal, N—H···O and weak C—H···O hydrogen bonds, and C—H···π interactions stabilize the crystal structure, forming a three-dimensional network (Table 1).

Experimental

0.002 mol of N'-(4-(trifluoromethyl)benzylidene-5-chloro-3-phenyl-1H-indole-2-carbohydrazide was reacted with 3 ml of mercaptoacetic acid in anhydrous benzene for 6 h using a Dean–Stark trap. Excess benzene was removed under reduced pressure. The residue was triturated with saturated sodium bicarbonate solution. The separated solid was filtered, washed with water and crystallized from ethanol. Orange crystalline solid. m.p. 510 K. IR (KBr) ν 3303 (indol N—H and amide N—H); 1717 (C═O),1655, (C═O) cm^-1; Analysis calculated for C₂₅H₁₇ClF₃N₃O₂S: C: 58.20; H: 3.32; N: 8.14%. Found: C: 57.18; H: 3.59; N: 7.87%.