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

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

doi:10.1107/s1600536810052359

Cited by 4 publications

(4 citation statements)

References 15 publications

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“…The bond lengths and angles are comparable with the values reported for related structures (Akkurt et al, 2007(Akkurt et al, , 2008(Akkurt et al, , 2011(Akkurt et al, , 2012.…”

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confidence: 79%

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(Z)-N′-(3-Ethyl-4-oxothiazolidin-2-ylidene)-2-[6-(4-methoxyphenyl)imidazo[2,1-b]thiazol-3-yl]acetohydrazide

et al. 2017

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The title compound, C 19 H 19 N 5 O 3 S 2 , crystallizes in the triclinic space group P1, with two independent molecules (A and B) in the asymmetric unit (Z 0 = 2). The imidazo [2,1-b] [1,3]thiazole ring systems in molecules A and B are essentially planar (r.m.s deviations = 0.004 and 0.005 Å , respectively), with dihedral angles of 1.1 (3) and 0.8 (3) , respectively, between the thiazole and imidazole rings. The mean planes of these ring systems make dihedral angles of 16.0 (2) and 61.9 (2) for molecule A, and 11.8 (2) and 74.3 (2) for molecule B, with the 1,3-thiazolidine and methoxy-substituted benzene rings, respectively. In the crystal, molecules are linked via N-HÁ Á ÁO hydrogen bonds, forming -A-B-A-Bchains along [100]. The chains are linked by C-HÁ Á ÁO hydrogen bonds, forming layers parallel to the ab plane. Structure descriptionContinuing our work on the synthesis and crystal structure analyses of imidazo[2,1-b]thiazole derivatives (Akkurt et al., 2007(Akkurt et al., , 2008(Akkurt et al., , 2011(Akkurt et al., , 2012, we report herein on the synthesis and crystal structure of the title compound.The asymmetric unit ( (2) for molecule A, and 11.8 (2) and 74.3 (2) for molecule B, with the 1,3- et al., 2007, 2008, 2011, 2012). In the crystal, molecules are linked via N-HÁ Á ÁO hydrogen bonds, forming -A-B-A-B-chains along [100]; see Table 1 and Fig. 2. The chains are linked by C-HÁ Á ÁO hydrogen bonds, forming layers parallel to the ab plane; see Table 1 and Fig. 3. Table 1 Hydrogen-bond geometry (Å , ). Symmetry codes: (i) x þ 1; y; z; (ii) Àx; Ày þ 1; Àz þ 2; (iii) x; y À 1; z. Figure 2A partial view along the b axis of the crystal packing of the title compound. The chains propagating along [100] are generated by N-HÁ Á ÁO hydrogen bonds (dashed lines; see Table 1). Figure 3A view along the c axis of the crystal packing of the title compound. The N-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds are shown as dashed lines (see Table 1). Figure 1View of the molecular structure of the two independent molecules (A and B) of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. RefinementCrystal data, data collection and structure refinement details are summarized in Table 2. A total of 15 reflections showing poor agreement between |F o | 2 and |F c | 2 were omitted in the final cycles of refinement.

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“…The bond lengths and angles are comparable with the values reported for related structures (Akkurt et al, 2007(Akkurt et al, , 2008(Akkurt et al, , 2011(Akkurt et al, , 2012.…”

supporting

confidence: 79%

“…Continuing our work on the synthesis and crystal structure analyses of imidazo[2,1-b]thiazole derivatives (Akkurt et al, 2007(Akkurt et al, , 2008(Akkurt et al, , 2011(Akkurt et al, , 2012, we report herein on the synthesis and crystal structure of the title compound.…”

Section: Structure Descriptionmentioning

confidence: 99%

(Z)-N′-(3-Ethyl-4-oxothiazolidin-2-ylidene)-2-[6-(4-methoxyphenyl)imidazo[2,1-b]thiazol-3-yl]acetohydrazide

et al. 2017

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“…For Schiff bases with applications in dyes and pigments, see: Taggi et al (2002). For related structures, see: Akkurt et al (2011); Lv et al (2009a,b); Yu & Lv (2010). For standard bond lengths, see: Allen et al (1987).…”

Section: Related Literaturementioning

confidence: 99%

“…On the industrial scale, they have wide range of applications such as dyes and pigments (Taggi et al, 2002). The crystal structures of some Schiff base hydrazines, viz., N′-(2-methoxybenzylidene) acetohydrazide (Yu & Lv, 2010) (Akkurt et al, 2011), N′-(3-methoxybenzylidene)acetohydrazide and N′-(3,4-dimethoxybenzylidene)acetohydrazide (Lv et al, 2009a,b). In view of the importance of hydrazides, the crystal structure of title compound (I) is reported.…”

Section: S1 Commentmentioning

confidence: 99%

(E)-N′-(4-Methoxybenzylidene)-2-m-tolylacetohydrazide

et al. 2012

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2-[6-(4-Bromophenyl)imidazo[2,1-b][1,3]thiazol-3-yl]-N-[8-(4-hydroxyphenyl)-2-methyl-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl]acetamide ethanol disolvate

et al. 2012

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In the title compound, C28H27BrN4O3S2·2C2H6O, the cyclohexane ring adopts a chair conformation. The imidazo[2,1-b][1,3]thiazole ring system is essentially planar with a dihedral angle of 1.1 (2)° between the thiazole and imidazole rings. The mean plane of this ring system makes dihedral angles of 8.11 (16) and 79.43 (17)°, respectively, with the bromo- and hydroxy-substituted benzene rings. In the 5-methyl-1,3-thiazolidin-4-one group, the S atom, the methyl group and the ring C atoms bonded to them are disordered over two sets of sites with refined occupancies of 0.610 (19) and 0.390 (19). The crystal structure features N—H⋯O, O—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds and C—H⋯π interactions. Furthermore, two weak π–π stacking interactions [centroid–centroid distances = 3.967 (3) and 3.892 (2) Å] are also observed.

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

Cited by 4 publications

References 15 publications

(Z)-N′-(3-Ethyl-4-oxothiazolidin-2-ylidene)-2-[6-(4-methoxyphenyl)imidazo[2,1-b]thiazol-3-yl]acetohydrazide

(Z)-N′-(3-Ethyl-4-oxothiazolidin-2-ylidene)-2-[6-(4-methoxyphenyl)imidazo[2,1-b]thiazol-3-yl]acetohydrazide

(E)-N′-(4-Methoxybenzylidene)-2-m-tolylacetohydrazide

2-[6-(4-Bromophenyl)imidazo[2,1-b][1,3]thiazol-3-yl]-N-[8-(4-hydroxyphenyl)-2-methyl-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl]acetamide ethanol disolvate

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