N-(2,4-Dioxo-1,3-thia­zolidin-3-yl)-2-(4-isobutyl­phen­yl)propanamide

Hoong-Kun Fun; Jia Hao Goh; A C Vinayaka; B Kalluraya

doi:10.1107/S160053680903027X

. 2009 Aug 8;65(Pt 9):o2094. doi: 10.1107/S160053680903027X

N-(2,4-Dioxo-1,3-thiazolidin-3-yl)-2-(4-isobutylphenyl)propanamide

Hoong-Kun Fun ^a,^*,^‡, Jia Hao Goh ^a, A C Vinayaka ^b, B Kalluraya ^b

PMCID: PMC2970021 PMID: 21577510

Abstract

In the title compound, C₁₆H₂₀N₂O₃S, the thiazolidine ring is approximately planar [maximum deviation = 0.020 (2) Å] and forms a dihedral angle of 86.20 (11)° with the benzene ring. The mean plane through the propanamide unit forms dihedral angles of 88.54 (12) and 76.36 (12)°, respectively, with the thiazolidine and benzene rings. In the crystal structure, molecules are linked into chains along the a axis by N—H⋯O interactions. These chains are interconnected into two-dimensional arrays parallel to the ab plane by three different C—H⋯O interactions. The crystal structure is further stabilized by weak intermolecular C—H⋯π and N⋯O [2.713 (2) Å] interactions.

Related literature

For general background to the synthesis, pharmacological properties and applications of compounds incorporating ibuprofen, see: Aktay et al. (2005 ▶); Palaska et al. (2002 ▶); Verma & Saraf (2008 ▶). For related structures, see: Fun et al. (2009a ▶,b ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₆H₂₀N₂O₃S
M _r = 320.40
Orthorhombic,
a = 9.7305 (1) Å
b = 11.3991 (2) Å
c = 29.6323 (4) Å
V = 3286.78 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 100 K
0.24 × 0.21 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.951, T _max = 0.981
33569 measured reflections
3783 independent reflections
2927 reflections with I > 2σ(I)
R _int = 0.079

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.143
S = 1.20
3783 reflections
279 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903027X/tk2517sup1.cif

e-65-o2094-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903027X/tk2517Isup2.hkl

e-65-o2094-Isup2.hkl^{(185.6KB, 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
N2—H1N2⋯O3ⁱ	0.85 (3)	1.94 (3)	2.713 (2)	151 (2)
C2—H2A⋯O1ⁱⁱ	0.89 (3)	2.53 (3)	3.209 (3)	133 (3)
C2—H2B⋯O2ⁱⁱⁱ	0.92 (3)	2.45 (3)	3.371 (3)	174 (2)
C5—H5⋯O1^iv	1.02 (3)	2.46 (2)	3.190 (3)	127.6 (18)
C2—H2A⋯Cg2ⁱⁱ	0.90 (3)	2.99 (3)	3.474 (3)	116 (2)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . Cg2 is the centroid of the C6–C11 ring ring.

Acknowledgments

HKF and JHG thank Universiti Sains Malaysia (USM) for a Research Universiti Golden Goose Grant (No. 1001/PFIZIK/811012). JHG thanks USM for the award of a USM Fellowship.

supplementary crystallographic information

Comment

The synthesis of compounds incorporating ibuprofen has been attracting widespread attention due to their diverse pharmacological properties, such as anti-microbial, anti-inflammatory, analgesic and anti-tumor activities (Palaska et al., 2002; Aktay et al., 2005). There are numerous biologically active molecules with five-membered rings, containing two heteroatoms. For example, thiazolidine is an important scaffold known to be associated with several biological activities (Verma & Saraf, 2008). In view of the above, the synthesis of a new series of 2,4-dioxo-1,3-thiazolidins containing ibuprofen was undertaken. We report here one of these crystal structures, (I).

In (I), Fig. 1, the thiazolidine ring (C1-C3/N1/S1) is approximately planar, with a maximum deviation of 0.020 (2) Å for atom C3. The thiazolidine ring is almost perpendicular to the C6-C12 benzene ring, forming a dihedral angle of 86.20 (11)°. The mean plane through the propanamide (C4/C5/N2/O3) forms dihedral angles of 88.54 (12)° and 76.36 (12)°, respectively, with the thiazolidine and benzene rings. The bond lengths are comparable to those found in closely related structures (Fun at al., 2009a,b).

In the crystal structure (Fig. 2), the molecules are linked into chains along the a axis by N2—H1N2···O3 interactions (Table 1). These chains are interconnected into 2-D arrays parallel to the ab plane by additional C2—H2A···O1, C2—H2B···O2 and C5—H5···O1 interactions (Table 1). The crystal structure is further stabilized by short N2···O3 contacts of 2.713 (2) Å [symmetry code: -1/2+x, 1/2-y, 1-z] and by weak C2—H2A···Cg2 interactions (Table 1).

Experimental

Compound (I) was obtained by refluxing 4-amino-5-[1-(4-isobutylphenyl)ethyl]-4H-1,3,4-oxadiazole-2-thiol (0.005 mol) and ethylchloroacetate (0.005 mol) in a solution comprising ethanol (20 ml) and pyridine (2 ml) in an oil bath for 8 h. The solid product obtained was collected by filtration, washed with ethanol and dried. It was then recrystallized using ethanol. Single crystals were obtained by slow evaporation from an ethanol solution of (I). Yield was 84 %. M.p. 466 K.