Acta Crystallographica Section B

Structural Science

Volume 61, Part 2 (April 2005)

research papers

Acta Cryst. (2005). B61, 192-199 [ doi:10.1107/S0108768105006075 ]

Structural characterization of [1,4]diazepino[6,5-b]indoles by powder diffraction

S. Y. Ryabova, N. A. Rastorgueva, E. J. Sonneveld, R. Peschar, H. Schenk, V. A. Tafeenko, L. A. Aslanov and V. V. Chernyshev

Abstract: As part of a systematic structural study of potentially pharmacologically active [1,4]diazepino[6,5-b]indoles, the crystal structures of nine compounds have been determined from laboratory powder diffraction data. The investigated compounds are: 2-oxo-1-(4-nitrophenyl)-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole-4-oxide, C₁₇H₁₂N₄O₄ (1a); 2-oxo-1-phenyl-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole-4-oxide, C₁₇H₁₃N₃O₂ (1b); 2-oxo-1-(4-ethoxyphenyl)-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole-4-oxide, C₁₉H₁₇N₃O₃ (1c); 2-oxo-1-(4-chlorophenyl)-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole-4-oxide, C₁₇H₁₂N₃O₂Cl (1d); 2-oxo-1-(4-cyanophenyl)-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole-4-oxide, C₁₈H₁₂N₄O₂ (1e); 6-methyl-2-oxo-1-phenyl-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indole-4-oxide, C₁₈H₁₅N₃O₂ (1f); 2-formyl-3-[N'-( [omega] -chloracetyl)-N'-(4-nitrophenyl)]aminoindole, C₁₇H₁₂N₃O₄Cl (2a); 2-formyl-3-[N'-( [omega] -chloracetyl)-N'-(4-nitrophenyl)]aminoindole solvate with toluene (2:1), C₁₇H₁₂N₃O₄Cl·0.5C₇H₈ (2as); 2-formyl-3-[N'-( [omega] -chloracetyl)-N'-(4-cyanophenyl)]aminoindole, C₁₈H₁₂N₃O₂Cl (2e). Compounds (1a)-(1f) crystallize in non-centrosymmetric triclinic, monoclinic and orthorhombic space groups. The three-dimensional structures of (1a)-(1e) demonstrate identical intermolecular NH(indole)O [leftwards arrow] N hydrogen bonds, which form linear chains of connected molecules. A comparison of the crystal structures (2a), (2e) and (2as) shows that the solvent used in the re-crystallization of (2a) and (2e), which are intermediates in the synthesis of (1a) and (1e), affects the intermolecular hydrogen-bond formation and, as a result, leads to essentially different yields of the goal products.

Keywords: X-ray powder diffraction; structure determination from powder data; grid search; Rietveld refinement.


	Rietveld powder data file (CIF format) (233.7 kbytes) Contains datablock WS5016_1A

	Rietveld powder data file (CIF format) (250.0 kbytes) Contains datablock WS5016_1B

	Rietveld powder data file (CIF format) (248.9 kbytes) Contains datablock WS5016_1C

	Rietveld powder data file (CIF format) (231.9 kbytes) Contains datablock WS5016_1D

	Rietveld powder data file (CIF format) (215.6 kbytes) Contains datablock WS5016_1E

	Rietveld powder data file (CIF format) (213.8 kbytes) Contains datablock WS5016_1F

	Rietveld powder data file (CIF format) (268.0 kbytes) Contains datablock WS5016_2A

	Rietveld powder data file (CIF format) (248.2 kbytes) Contains datablock WS5016_2AS

	Rietveld powder data file (CIF format) (260.8 kbytes) Contains datablock WS5016_2E

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