SYNTHESIS AND X-RAY STRUCTURAL CHARACTERIZATION OF 1-(5-BROMOBENZOFURAN-2-YL)-2MESITYLETHANONEOXIME AND 1-(5-BROMOBENZOFURAN-2-YL)-2-MESITYLETHANONE-O(2-PHENYLACETYL)OXIME

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Yakali G., Barim E., KIRILMIŞ C., AYGÜN M.

JOURNAL OF THE CHILEAN CHEMICAL SOCIETY, cilt.61, sa.3, ss.3140-3143, 2016 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 61 Sayı: 3
  • Basım Tarihi: 2016
  • Doi Numarası: 10.4067/s0717-97072016000300027
  • Dergi Adı: JOURNAL OF THE CHILEAN CHEMICAL SOCIETY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.3140-3143
  • Anahtar Kelimeler: Benzofuran derivatives, Oxime derivatives, Crystal structure, X-ray, 2D Network, ANTIMICROBIAL ACTIVITY, DERIVATIVES, OXIMES, BENZOFURAN, PATTERNS, ACID
  • Dokuz Eylül Üniversitesi Adresli: Evet

Özet

The selected molecules of benzofuran derivatives were synthesized and their structures were studied using the X-ray crystallography and spectroscopic methods. The 1-(5-bromobenzofurane-2-yl)-2-mesitylethanoneoxime (I), C19H18BrNO2, and 1-(5-bromobenzofuran-2-yl)-2-mesitylethanone-O-(2-phenylacetyl) oxime (II), C27H24BrNO3, crystallize in the monoclinic crystal system in space group P2(1)/c with Z = 4 and in the triclinic system in space group P-1 with Z= 2, respectively. The both compounds adopt Z conformation. The compound (I) consists of a dimeric arrangement of molecules around an inversion centre formed via a O-H center dot center dot center dot N intermolecular hydrogen bond linking the molecules - Along the a axis. This centrosymmetric hydrogen-bonded dimers are formed with an R-2(2)(6) ring motif. The compound (II) forms one dimensional infinite chain via C-H center dot center dot center dot O hydrogen bond along the a axis. Moreover, in the crystal structures of (I), (II) weak C-H center dot center dot O, C-H center dot center dot center dot pi and pi center dot center dot center dot pi interactions serve to organize formation of a two dimensional network. Moreover a short N1-N1 intermolecular contact [2.89 angstrom] is observed between inversion-related chains in the crystal structure of (I). The two compounds have essentialy similar bond lengths and angles. The prominent discrepancy is observed for the fragment attaching benzofuran ring with mesityl group. Benzofuran groups and other ring groups are almost planar in the crystal structures of (I) and (II).