(Pyrazinecarbonyl)hydrazone halobenzaldehydes: supramolecular arrays generated by face to face stacking of ribbons, formed from C–H–O interactions

Baddeley, Thomas C.; Howie, R. Α.; Lima, Camilo Henrique da Silva; Kaiser, Carlos R.; Souza, Marcus V. N. de; Wardell, Jámes L.; Wardell, Solange M. S. V.

doi:10.1524/zkri.2009.1182

Cited by 16 publications

(5 citation statements)

References 17 publications

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“…In continuation of our studies on pyrazinamide derivatives (Wardell et al, 2008;Baddeley et al, 2009;Howie et al, 2010aHowie et al, , 2010bHowie et al, , 2010cHowie et al, , 2010d, we report the structure of title compound, (I).…”

Section: Commentmentioning

confidence: 69%

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N-(2-Chloroethyl)pyrazine-2-carboxamide

Lima

Souza

Wardell³

et al. 2010

Acta Cryst E

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In the title molecule, C7H8ClN3O, the pyrazine and amide groups are almost co-planar [N—C—C—N torsion angle = −2.4 (2) °], a conformation stabilized by an intramolecular N—H⋯N hydrogen bond. The chloroethyl group lies out of the plane [N—C—C—Cl = −65.06 (17) °]. In the crystal, the presence of N—H⋯N hydrogen bonds leads to the formation of a C(6) supramolecular chain along the b axis. The carbonyl-O atom accepts two C—H⋯O interactions. These, plus Cl⋯Cl short contacts [3.3653 (6) Å], consolidate the packing of the chains in the crystal.

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Section: Commentmentioning

confidence: 69%

“…For structural studies on pyrazinamide derivatives; see: Wardell et al (2008); Baddeley et al (2009) ;Howie et al (2010a,b,c,d Table 1 Hydrogen-bond geometry (Å , ). Symmetry codes: (i) Àx þ 1; y À 1 2 ; Àz þ 3 2 ; (ii) Àx þ 1; y þ 1 2 ; Àz þ 3 2 ; (iii) Àx þ 2; Ày þ 2; Àz þ 1; (iv) Àx þ 1; Ày þ 2; Àz þ 1.…”

Section: Related Literaturementioning

confidence: 99%

N-(2-Chloroethyl)pyrazine-2-carboxamide

Lima

Souza

Wardell³

et al. 2010

Acta Cryst E

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“…Pyrazinamide has well known anti-mycobacterial activity and is the one of the most important drugs used in tuberculosis treatment (Chaisson et al, 2002;Gordin et al, 2000;de Souza, 2006). In continuation of our studies on pyrazinamide derivatives (Wardell et al, 2008;Baddeley et al, 2009;Howie et al, 2010a,b,c,d), we report the structure of N-(4bromophenyl)pyrazine-2-carboxamide, the title compound, (I).…”

Section: S1 Commentmentioning

confidence: 71%

“…For the antimycobacterial activity of pyrazinamide, see: Chaisson et al (2002); Gordin et al (2000); de Souza (2006). For structural studies of pyrazinamide derivatives; see: Baddeley et al (2009); Howie et al (2010a,b,c,d). For the synthesis, see: Wardell et al (2008); Vontor et al (1989).…”

Section: Related Literaturementioning

confidence: 99%

N-(4-Bromophenyl)pyrazine-2-carboxamide

Ferreira

Souza

Wardell³

et al. 2010

Acta Cryst E

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The molecule of the title compound, C11H8BrN3O, is close to planar (r.m.s. deviation of all 16 non-H atoms = 0.103 Å), a conformation stabilized by an intramolecular N—H⋯N hydrogen bond, which generates an S(5) ring. In the crystal structure, supramolecular chains mediated by C—H⋯O contacts (along a) are linked into a double layer via N⋯Br halogen bonds [3.207 (5) Å] and C—Br⋯π interactions [Br⋯ring centroid(pyrazine) = 3.446 (3) Å]. The layers stack along the b axis via weak π–π interactions [ring centroid(pyrazine)⋯ring centroid(benzene) distance = 3.803 (4) Å].

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“…In the X = o-Cl structure, in addition to incorporating N-HÁ Á ÁO hydrogen bonding, a C-HÁ Á ÁO hydrogen bond is formed between the pyrazine ring and the amide group of a neighbouring molecule. The intermolecular C-HÁ Á ÁO hydrogen bonding generates a ribbon-like structure that leads to -stacking between the layers and the final 3D structure (Baddeley et al, 2009).…”

Section: Figurementioning

confidence: 99%

A survey of interactions in crystal structures of pyrazine-based compounds

Taghipour

Mirzaei

2019

Acta Crystallogr C

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The important role of pyrazine (pz) and its derivatives in fields such as biochemistry and pharmacology, as well as in the study of magnetic properties, is surveyed. Recognition of these properties without extensive investigations into their structural properties is not possible. This review summarizes interactions that exist between these organic compounds by themselves in the solid state, as well as those in coordination polymers with metal ions and in polyoxometalatebased hybrids. Complexes based on pyrazine ligands can generate metal-organic framework (MOF) structures that bind polyoxometalates (POMs) through covalent and noncovalent interactions. Some biological and magnetic properties involving these compounds are considered and the effect of hydrogen bonding on their supramolecular architectures is highlighted. feature articles 232 Taghipour and Mirzaei A survey of interactions of pyrazine-based compounds Acta Cryst. (2019). C75, 231-247 feature articles 234 Taghipour and Mirzaei A survey of interactions of pyrazine-based compounds Acta Cryst. (2019). C75, 231-247 feature articles Acta Cryst. (2019). C75, 231-247 Taghipour and Mirzaei A survey of interactions of pyrazine-based compounds 237 Figure 9Structure of [Cu 2 (PZOAPZ-H)Br 3 (H 2 O) 2 ]. Reproduced from Grove et al. (2004) with permission. feature articles Acta Cryst. (2019). C75, 231-247 Taghipour and Mirzaei A survey of interactions of pyrazine-based compounds 245

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(Pyrazinecarbonyl)hydrazone halobenzaldehydes: supramolecular arrays generated by face to face stacking of ribbons, formed from C–H–O interactions

Cited by 16 publications

References 17 publications

N-(2-Chloroethyl)pyrazine-2-carboxamide

N-(2-Chloroethyl)pyrazine-2-carboxamide

N-(4-Bromophenyl)pyrazine-2-carboxamide

A survey of interactions in crystal structures of pyrazine-based compounds

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