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Synthesis and crystal structure determination of 6,7‐dihydro‐2‐methoxy‐4‐(substituted)‐5 H ‐benzo[6,7]cyclohepta[1,2‐ b ]pyridine‐3‐carbonitrile
Author(s) -
Moustafa A. M.,
Girgis A. S.
Publication year - 2007
Publication title -
crystal research and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.377
H-Index - 64
eISSN - 1521-4079
pISSN - 0232-1300
DOI - 10.1002/crat.200610835
Subject(s) - triclinic crystal system , chemistry , monoclinic crystal system , substituent , pyridine , crystallography , hydrogen bond , crystal structure , valency , stereochemistry , molecule , medicinal chemistry , organic chemistry , linguistics , philosophy
The compounds 6,7‐dihydro‐2‐methoxy‐4‐(4‐methylphenyl)‐5 H ‐benzo[6.7]cyclohepta[1,2 ‐b ]pyridine‐3‐carbonitrile (compound IIIa) and 4‐(4‐chlorophenyl)‐6,7‐dihydro‐2‐methoxy‐5 H ‐benzo[6,7]cyclohepta[1,2‐ b ]pyridine‐3‐carbonitrile (compound IIIb) were synthesized and their structures have been determined from three dimensional X‐ray data using direct method and refined by full matrix least squares with anisotropic thermal parameters for non‐hydrogen atoms to conventional R(gt) of 0.036 and 0.038 for the two compounds respectively. For compound (IIIa) the crystals are monoclinic, space group C c , with a=11.2909 (5) Å, b=17.7755(8) Å, c=9.1437(4) Å and β=95.428(3)°, while the crystals of the second compound (IIIb) are triclinic, space group P1, with a=8.7465(3)Å, b=10.3958(3)Å, c=10.9011(4)Å, α= 108.3870(10)°, β=101.3741(12)°, γ=97.9594(12)°. The molecular structure of the two compounds have nearly the same configuration, where the cyclohepta ring takes the boat shape and the methoxy and the carbonitrile groups are attached at the same position C 2 and C 8 . The difference occurs only at the position C 4 , where the substituent is methylphenyl for compound (IIIa) and chlorophenyl for the other. The bond lengths, valency angles and the hydrogen bonding were calculated and fully discussed. (© 2007 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim)