TY - JOUR
T1 - Centrosymmetric structures of three substituted malonic acids
AU - Harrison, Jerry Joe Ebow Kingsley
AU - Kingsford-Adaboh, Robert
AU - Ueda, Syunsuke
AU - Gotoh, Kazuma
AU - Ishida, Hiroyuki
PY - 2011/3
Y1 - 2011/3
N2 - Crystal structures of 2-methylmalonic acid, 2-ethylmalonic acid and 2-phenylmalonic acid, which are derivatives of malonic acid and have found usefulness in diagnostics and biochemical evaluations as markers and organic synthesis, are reported. 2-Methylmalonic acid and 2-ethylmalonic acid both crystallize in triclinic P-1 space group with cell parameters of a = 5.1033(7), b = 5.4231(7), c = 10.0887(14) Å, α = 88.074(4), β = 89.999(5) and γ = 67.955(4)° for 2-methylmalonic acid, and a = 5.2073(4), b = 7.2258(6), c = 8.5655(6) Å, α = 88.086(2), β = 75.307(2) and γ = 85.904(3)° for 2-ethylmalonic acid, 2-phenylmalonic acid on the other hand crystallizes in monoclinic P21/c with cell parameters a = 8.6494(4), b = 5.48733(19), c = 17.1706(6) Å and β = 90.1068(17)°. The observed topology of the hydrogen bonding network is to a large extent dictated by the symmetrical substitution pattern with an open arrangement of hydrogen bonds. Each of the C=O double bonds in both 2-methylmalonic acid and 2-ethylmalonic acid is translationally offset, forming planar centrosymmetric carboxy-dimers. Molecules related by centre of inversion in spite of the constraints imposed by substituents are linked by O-H⋯O hydrogen bonds. This results in the formation of parallel zig-zag chains running along the [101] direction. In 2-phenylmalonic acid, the zig-zag molecular residue is parallely stacked with successive catemers. These laterally displaced catemers are also coiled in a twofold twist on the screw axis (x, 1/2 + y, 1/2 - z) along the b-glide (x, 1/2 - y, 1/2 + z) when viewed along the (101) plane.
AB - Crystal structures of 2-methylmalonic acid, 2-ethylmalonic acid and 2-phenylmalonic acid, which are derivatives of malonic acid and have found usefulness in diagnostics and biochemical evaluations as markers and organic synthesis, are reported. 2-Methylmalonic acid and 2-ethylmalonic acid both crystallize in triclinic P-1 space group with cell parameters of a = 5.1033(7), b = 5.4231(7), c = 10.0887(14) Å, α = 88.074(4), β = 89.999(5) and γ = 67.955(4)° for 2-methylmalonic acid, and a = 5.2073(4), b = 7.2258(6), c = 8.5655(6) Å, α = 88.086(2), β = 75.307(2) and γ = 85.904(3)° for 2-ethylmalonic acid, 2-phenylmalonic acid on the other hand crystallizes in monoclinic P21/c with cell parameters a = 8.6494(4), b = 5.48733(19), c = 17.1706(6) Å and β = 90.1068(17)°. The observed topology of the hydrogen bonding network is to a large extent dictated by the symmetrical substitution pattern with an open arrangement of hydrogen bonds. Each of the C=O double bonds in both 2-methylmalonic acid and 2-ethylmalonic acid is translationally offset, forming planar centrosymmetric carboxy-dimers. Molecules related by centre of inversion in spite of the constraints imposed by substituents are linked by O-H⋯O hydrogen bonds. This results in the formation of parallel zig-zag chains running along the [101] direction. In 2-phenylmalonic acid, the zig-zag molecular residue is parallely stacked with successive catemers. These laterally displaced catemers are also coiled in a twofold twist on the screw axis (x, 1/2 + y, 1/2 - z) along the b-glide (x, 1/2 - y, 1/2 + z) when viewed along the (101) plane.
KW - 2-Ethylmalonic acid
KW - 2-Methylmalonic acid
KW - 2-Phenylmalonic acid
KW - Biochemical markers
KW - Catemer
KW - Centrosymmetric dimers
KW - Hydrogen bonding
UR - http://www.scopus.com/inward/record.url?scp=79952191479&partnerID=8YFLogxK
U2 - 10.1007/s10870-010-9878-4
DO - 10.1007/s10870-010-9878-4
M3 - Article
AN - SCOPUS:79952191479
SN - 1074-1542
VL - 41
SP - 306
EP - 311
JO - Journal of Chemical Crystallography
JF - Journal of Chemical Crystallography
IS - 3
ER -