TY - JOUR
T1 - Peri interactions in naphthalene diketones
T2 - A preference for (Z,Z) conformations
AU - Cohen, Shmuel
AU - Thirumalaikumar, Muniappan
AU - Pogodin, Sergey
AU - Agranat, Israel
PY - 2004/8
Y1 - 2004/8
N2 - The crystal structures of 1,8-dibenzoylnaphthalene (9), 1,4,5,8-tetrabenzoylnaphthalene (10), and 1,8-diacetylnaphthalene (11) have been determined by X-ray diffraction. Diketone 9 crystallizes in triclinic space group P1̄ with a = 7.924(2), b = 14.068(3), c = 7.876(1) Å, a = 99.47(2), β = 90.58(1), γ = 91.43(2)°. Tetraketone 10 crystallizes in monoclinic space group P21/c a = 7.374(4), b = 11.960(5), c = 15.524(5) Å, β = 93.15(5)°. Diketone 11 crystallizes in orthorhombic space group Pbca a = 6.986(3), b = 15.946(4), c = 8.257(1) Å. Each of these naphthalene ketones adopt a (Z,Z) conformation, with torsion angles O-C-C1-C8a/O-C-C8-C 8a of 49.8°/44.5° (9), 52.1°/46.6° (10), and 44.8°/42.4° (11). The structures 9-11 are overcrowded with the distances between two neighboring carbonyl carbon atoms being significantly shorter than the sum of the van der Waals radii of two carbon atoms (342 pm): 293.4 pm (9), 281.6 pm (10), and 293.0 pm (11).
AB - The crystal structures of 1,8-dibenzoylnaphthalene (9), 1,4,5,8-tetrabenzoylnaphthalene (10), and 1,8-diacetylnaphthalene (11) have been determined by X-ray diffraction. Diketone 9 crystallizes in triclinic space group P1̄ with a = 7.924(2), b = 14.068(3), c = 7.876(1) Å, a = 99.47(2), β = 90.58(1), γ = 91.43(2)°. Tetraketone 10 crystallizes in monoclinic space group P21/c a = 7.374(4), b = 11.960(5), c = 15.524(5) Å, β = 93.15(5)°. Diketone 11 crystallizes in orthorhombic space group Pbca a = 6.986(3), b = 15.946(4), c = 8.257(1) Å. Each of these naphthalene ketones adopt a (Z,Z) conformation, with torsion angles O-C-C1-C8a/O-C-C8-C 8a of 49.8°/44.5° (9), 52.1°/46.6° (10), and 44.8°/42.4° (11). The structures 9-11 are overcrowded with the distances between two neighboring carbonyl carbon atoms being significantly shorter than the sum of the van der Waals radii of two carbon atoms (342 pm): 293.4 pm (9), 281.6 pm (10), and 293.0 pm (11).
KW - Conformation
KW - Crystal structures
KW - Nonplanarity
KW - Overcrowding
KW - PAHs
UR - http://www.scopus.com/inward/record.url?scp=3843072383&partnerID=8YFLogxK
U2 - 10.1023/B:STUC.0000026750.39809.07
DO - 10.1023/B:STUC.0000026750.39809.07
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AN - SCOPUS:3843072383
SN - 1040-0400
VL - 15
SP - 339
EP - 346
JO - Structural Chemistry
JF - Structural Chemistry
IS - 4
ER -