Crystal structures and charge distributions in 2-phenyl-imidazo[1,2-a]-pyridine and two related salts

Abstract

X-ray structural investigations of 2-phenylimidazo[l,2-a]pyridine and two of its salts: 1-methyl-2-phenyl-imidazo[l,2-a]pyridinium iodide and l-methyl-2-phenyl-6-nitro-imidazo[l,2-a]pyridinium iodide (R = 0.040, 0.032, 0.034 respectively), together with semiempirical calculations of charge distribution, have been carried out. The insertion of nitro-group does not cause any fundamental changes in geometry, but induces changes in the electron density distribution in the bicyclic unit. As a result rather short cation-anion contacts (I...C = 3.52 Ä) are observed in structure III.

Crystal structure, DFT calculation, Hirshfeld surface analysis and energy framework study of 6-bromo-2-(4-bromophenyl)imidazo[1,2-a]pyridine

“…HURZOL (Yang et al, 2015) 6-methylimidazo[1,2-a]pyridin-3-yl thiocyanate 3-chlorophenyl 33.8, 27.7 KABMIM (Yang et al, 2016) 6-methyl-3-nitrosoimidazo[1,2-a]pyridinyl 3-chlorophenyl 6.8 MIXZOJ (Anaflous et al, 2008a) N-(imidazo[1,2-a]pyridin-3-yl)acetamide phenyl 9.0 MIXZUP (Anaflous et al, 2008b) imidazo[1,2-a]pyridinyl-3-carbaldehyde phenyl 28.6 MONREO (Velá zquez-Ponce et al, 2013) 3-nitrosoimidazo[1,2-a]pyridinyl phenyl 17.4, 4.9 NOGRIM (Marandi et al, 2014) 3-(t-butylamino)-imidazo[1,2-a]pyridinyl-8-carboxylic acid 3-nitrophenyl 16.8 OMIDEV (Samanta et al, 2016) 3-iodo-8-methyl-imidazo[1,2-a]pyridinyl phenyl 36.1, 34.4 QUQSEC (Ravi et al, 2016) 6-methyl-3-(methylsulfanyl)imidazo[1,2-a]pyridinyl 4-chlorophenyl 38.1 RELQUW (Yan et al, 2012) 8-methyl-3-nitroimidazo[1,2-a]pyridinyl phenyl 47.5 RUJNEQ (Li et al, 2009) imidazo[1,2-a]pyridinyl-3-carbaldehyde 4-chlorophenyl 34.6, 33.5 TUZYEU (Zhang et al, 2016) 6-fluoro-3-nitro-imidazo[1,2-a]pyridinyl phenyl 43.8, 37.9 UTITEX (Chunavala et al, 2011) ethyl 7-methylimidazo[1,2-a]pyridinyl-3-carboxylate phenyl 39.6 YEDHIY (Georges et al, 1993) 6-chloro-N,N-dipropylimidazo[1,2-a] pyridinyl-3-acetamide 4-chlorophenyl 15.2 ZUSSAJ (Xiao et al, 2015) 3-chloro-imidazo[1,2-a]pyridinyl 4-methylphenyl 12.0, 0.3 Non-3-(substituted)imidazo[1,2-a]pyridinyl BISDUF (Kutniewska et al, 2018) imidazo[1,2-a]pyridinyl 2-hydroxy-5-methoxyphenyl 6.0 BISFAN (Kutniewska et al, 2018) imidazo[1,2-a]pyridinyl 2-hydroxy-4-bromophenyl 4.2 CAJTIQ (Aslanov et al, 1983) 6-nitro-imidazo[1,2-a]pyridinyl phenyl 3.3 FEMQOF (Kurteva et al 2012) imidazo[1,2-a]pyridinyl 4-methoxyphenyl 12.5 JEBZEY (Zhu et al, 2017) imidazo[1,2-a]pyridinyl isophthalonitrile 46.4 MIQSUD (Jin et al, 2019) 2-(imidazo[1,2-a]pyridin-5-yl)propan-2-ol phenyl 2.7 NAGGEH (Tafeenko et al, 1996) imidazo[1,2-a]pyridinyl phenyl 4.4 NONFOM (Mutai et al, 2008) imidazo[1,2-a]pyridinyl 2-hydroxyphenyl 6.7 NUBVUD (Seferog lu et al, 2015) 7-methylimidazo[1,2-a]pyridinyl 4-methoxyphenyl 0.7 NUBWAK (Seferog lu et al, 2015) 7-methyl-imidazo[1,2-a]pyridinyl phenyl 5.3 QODZUG (Mutai et al, 2014) imidazo[1,2-a]pyridinyl-6-carbonitrile 2-hydroxyphenyl 2.8 TIDVIN (Donohoe et al, 2012) 6-bromo-imidazo[1,2-a]pyridinyl phenyl 2.4 VEGKAU …”

2-(4-Bromophenyl)oxazolo[3,2-a]pyrimidinium perchlorate

“…From a search of the Cambridge Structural Database (Version 5.27; Allen, 2002), we found NÁ Á ÁH hydrogen bonding for two analogs of the salt (2), viz. 6-nitro-2-phenylimidazo[1,2-a]pyrimidine (Aslanov et al, 1983) and 2-phenylimidazo[1,2-a]pyrimidine (Tafeenko et al, 1996), with NÁ Á ÁH distances of 2.53 and 2.50 Å , respectively.…”

2-(4-Bromophenyl)-5,7-dimethyl[1,3]oxazolo[3,2-a]pyrimidin-4-ium perchlorate

“…From a search of the Cambridge Structural Database (Version 5.27; Allen, 2002), we found N-HÁ Á ÁN hydrogen bonding for two analogs of the salt (2), viz. 6nitro-2-phenylimidazo[1,2-a]pyridine (Aslanov et al, 1983) and 2-phenylimidazo[1,2-a]pyridine (Tafeenko et al, 1996), with NÁ Á ÁH distances of 2.53 and 2.50 Å , respectively. Weak C-HÁ Á ÁO interactions (Table 2) are observed in the crystal structure of (2).…”