TY - JOUR
T1 - X-ray crystal structures of two polymorphic forms, monoclinic and triclinic, of
T2 - 1-[(E)-2-(4-bromophenyl)-1-diazenyl]-3-({3-[(E)-2-(4-bromophenyl) -1-diazenyl]-6-ethylhexahydro-1-pyrimidinyl}methyl)-4-ethylhexahydropyrimidine
AU - Tingley, Reid
AU - Bertolasi, Valerio
AU - Vaughan, Keith
PY - 2005/10/1
Y1 - 2005/10/1
N2 - 1-[(E)-2-(4-bromophenyl)-1-diazenyl]-3-({3-[(E)-2-(4-bromophenyl) -1-diazenyl]-6-ethylhexahydro-1-pyrimidinyl}methyl)-4-ethylhexahydropyrimidine (1) has been synthesized by reaction of a mixture of formaldehyde and 1,3-pentanediamine{DYTEK® EPdiamine} with p-bromobenzenediazonium chloride. This compound crystallizes in two polymorphic forms 1-α and 1-β whose crystal structures have been determined by single crystal X-ray diffraction analysis. Both polymorphs 1-α and 1-β display crystallographic disorder within the hexahydropyrimidine rings. The molecule of 1 is built up of two equivalent 3-(aryldiazenyl)-6-ethylhexahydro-1-pyrimidinyl groups in the s-trans orientation around the central methylene group (C13). In both structures the triazene moieties adopt the anti configuration around the N=N bonds, displaying significant π-conjugation. The crystal packings are determined only by van der Waals interactions. The crystal structures of 1-α and 1-β are compared with the previously reported structure of the 5,5-dimethylhexahydropyrimidine analogue 3. Compounds 1 and 3 are isomeric with respect to the hexahydropyrimidine moiety. The structures of 1 and 3 are very different in one respect; in 1 the aryldiazenyl-hexahydropyrimidinyl groups are in the s-trans orientation around the central methylene group, whereas in 3 the arrangement of the aryldiazenylhexahydropyrimidinyl groups is the s-cis orientation. Crystal data: 1-α C25H34N 8Br2, monoclinic, space group P2(1)/c, a = 9.2150(3), b = 19.4059(6), c = 15.4324(5) Å, β = 98.738(1)°, V = 2727.7(2) Å3, for Z = 4; 1-β C25H34N 8Br2, triclinic, space group P-1, a = 9.6009(3), b = 10.7509(4), c = 14.2169(5) Å, α = 99.830(2), β = 105.973(3), γ = 95.578(1)°, V = 1373.9(1) Å3, for Z = 2.
AB - 1-[(E)-2-(4-bromophenyl)-1-diazenyl]-3-({3-[(E)-2-(4-bromophenyl) -1-diazenyl]-6-ethylhexahydro-1-pyrimidinyl}methyl)-4-ethylhexahydropyrimidine (1) has been synthesized by reaction of a mixture of formaldehyde and 1,3-pentanediamine{DYTEK® EPdiamine} with p-bromobenzenediazonium chloride. This compound crystallizes in two polymorphic forms 1-α and 1-β whose crystal structures have been determined by single crystal X-ray diffraction analysis. Both polymorphs 1-α and 1-β display crystallographic disorder within the hexahydropyrimidine rings. The molecule of 1 is built up of two equivalent 3-(aryldiazenyl)-6-ethylhexahydro-1-pyrimidinyl groups in the s-trans orientation around the central methylene group (C13). In both structures the triazene moieties adopt the anti configuration around the N=N bonds, displaying significant π-conjugation. The crystal packings are determined only by van der Waals interactions. The crystal structures of 1-α and 1-β are compared with the previously reported structure of the 5,5-dimethylhexahydropyrimidine analogue 3. Compounds 1 and 3 are isomeric with respect to the hexahydropyrimidine moiety. The structures of 1 and 3 are very different in one respect; in 1 the aryldiazenyl-hexahydropyrimidinyl groups are in the s-trans orientation around the central methylene group, whereas in 3 the arrangement of the aryldiazenylhexahydropyrimidinyl groups is the s-cis orientation. Crystal data: 1-α C25H34N 8Br2, monoclinic, space group P2(1)/c, a = 9.2150(3), b = 19.4059(6), c = 15.4324(5) Å, β = 98.738(1)°, V = 2727.7(2) Å3, for Z = 4; 1-β C25H34N 8Br2, triclinic, space group P-1, a = 9.6009(3), b = 10.7509(4), c = 14.2169(5) Å, α = 99.830(2), β = 105.973(3), γ = 95.578(1)°, V = 1373.9(1) Å3, for Z = 2.
KW - 1,3-pentanediamine
KW - Crystal structure
KW - DYTEK® EPdiamine
KW - Hexahydropyrimidine
KW - Polymorphism
KW - Triazene
KW - X-ray diffraction
UR - http://www.scopus.com/inward/record.url?scp=27144481041&partnerID=8YFLogxK
U2 - 10.1007/s10870-005-4552-y
DO - 10.1007/s10870-005-4552-y
M3 - Article
AN - SCOPUS:27144481041
SN - 1074-1542
VL - 35
SP - 821
EP - 828
JO - Journal of Chemical Crystallography
JF - Journal of Chemical Crystallography
IS - 10
ER -