2-[6-(4-Chloro­phen­yl)imidazo[2,1-b][1,3]thia­zol-2-yl]-N′-[(E)-4-meth­oxy­benzyl­idene]acetohydrazide

Mehmet Akkurt; Nuray Ulusoy Güzeldemirci; Berin Karaman; Orhan Büyükgüngör

doi:10.1107/S1600536810052359

. 2010 Dec 18;67(Pt 1):o184–o185. doi: 10.1107/S1600536810052359

2-[6-(4-Chlorophenyl)imidazo[2,1-b][1,3]thiazol-2-yl]-N′-[(E)-4-methoxybenzylidene]acetohydrazide

Mehmet Akkurt ^a,^*, Nuray Ulusoy Güzeldemirci ^b, Berin Karaman ^b, Orhan Büyükgüngör ^c

PMCID: PMC3050215 PMID: 21522689

Abstract

In the imidazo[2,1-b][1,3]thiazole group of the title compound, C₂₁H₁₇ClN₄O₂S, the dihedral angle between the thiazole and imidazole rings is 1.9 (2)°. The mean plane of this group makes dihedral angles of 5.5 (2) and 39.9 (2)° with the benzene rings of the chlorophenyl and methoxyphenyl groups, respectively. The dihedral angle between these two benzene rings is 34.4 (2)°. In the crystal, molecules are connected to each other by intermolecular N—H⋯O hydrogen bonds along the b axis, generating a C(4) chain. Weak C—H⋯π interactions also occur.

Related literature

For the biological activity of imidazo[2,1-b][1,3]thiazole derivatives, see: Andreani et al. (2005 ▶); Barradas et al. (2008 ▶); Hanson et al. (1991 ▶); Juspin et al. (2010 ▶); Shilcrat et al. (1991 ▶). For details of the synthesis, see: Gürsoy & Ulusoy Güzeldemirci (2007 ▶); Ulusoy Güzeldemirci & Küçükbasmacı (2010 ▶). For related structures, see: Akkurt et al. (2007 ▶, 2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₁H₁₇ClN₄O₂S
M _r = 424.91
Orthorhombic,
a = 13.4591 (6) Å
b = 4.7834 (3) Å
c = 30.4674 (14) Å
V = 1961.50 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 296 K
0.38 × 0.26 × 0.13 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.890, T _max = 0.961
10765 measured reflections
3304 independent reflections
2754 reflections with I > 2σ(I)
R _int = 0.092

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.164
S = 1.01
3304 reflections
265 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ▶), 1611 Friedel pairs
Flack parameter: 0.15 (11)

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 datablocks global, I. DOI: 10.1107/S1600536810052359/vm2066sup1.cif

e-67-0o184-sup1.cif^{(22KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052359/vm2066Isup2.hkl

e-67-0o184-Isup2.hkl^{(162.1KB, hkl)}

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

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

Cg1 is the centroid of the N1/N2/C7–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1ⁱ	0.86	2.08	2.835 (4)	146
C12—H12A⋯Cg1ⁱ	0.97	2.54	3.282 (5)	133

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

supplementary crystallographic information

Comment

Imidazo[2,1-b][1,3]thiazole derivatives have demonstrated a broad range of biological activities, including immunomodulatory (Hanson et al., 1991), antibacterial (Juspin et al., 2010), antiviral (Barradas, et al.., 2008), antitumoral (Andreani et al., 2005) and antiinflammatory (Shilcrat et al., 1991).

As part of our on-going research aiming on the synthesis of imidazo[2,1-b]thiazoles (Gürsoy & Ulusoy Güzeldemirci, 2007; Ulusoy Güzeldemirci & Küçükbasmacı, 2010) and their crystal structures (Akkurt et al., 2007, 2008), we report here the crystal structure of the title compound (I).

In the title molecule of (I), (Fig. 1), the bond lengths and bond angles are normal (Allen et al., 1987). The imidazo[2,1-b][1,3]thiazole group is essantially planar with a dihedral angle of 1.9 (2) ° between the thiazole and imidazole rings makes a dihedral angle of 2.99 (15)°.

The mean plane of the imidazo[2,1-b][1,3]thiazole group makes dihedral angles of 5.5 (2) and 39.9 (2) ° with the benzene rings of the chlorophenyl and methoxyphenyl groups, respectively. The dihedral angle between these two phenyl rings is 34.4 (2) °.

Molecules are connected to each other by intermolecular N—H···O hydrogen bonds along the b axis, generating a C(4) chain (Table 1, Fig. 2). In the crystal structure, a weak C—H···π interaction occurs.

Experimental

[6-(4-Chlorophenyl)imidazo[2,1-b]thiazol-3-yl]acetic acid hydrazide (0.005 mol) and 4-methoxybenzaldehyde (0.005 mol) were heated in 100 ml ethanol for 5 h. The precipitate obtained was purified by washing with hot ethanol. Yield: 88%. M.p.: 511.5–512.6 K. IR [ν, cm^-1, KBr]: 3212, 3138 (N—H), 1660 (C=O). Analysis calculated for C₂₁H₁₇ClN₄O₂S: C 59.36, H 4.03, N 13.19%. Found: C 59.25, H 3.94, N 13.18%.