Order and disorder in the structure of dibenzofuran, C12H8O

Reppart, W. J.; Gallucci, Judith; Lundstedt, Anna; Gerkin, R. E.

doi:10.1107/s0108270184008751

Cited by 27 publications

(25 citation statements)

References 4 publications

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“…1 shows two 4-dibenzofurancarboxaldehyde molecules related by a center of inversion, with bond lengths and bond angles specified. The average C--C bond length within the two benzenoid rings is 1.388 (9)A, typical of the average values for the benzenoid rings found in dibenzofuran [1.392 (7)A; Reppart, Gallucci, Lundstedt & Gerkin, 1984], 4-DIBENZO FURANCARBOXALDEHYDE fluorene [1.388 (9) A; and carbazole [1.388 (4) A; Gerkin & Reppart, 1986]. The average interior angle for the two benzenoid rings is 120.0 (2.6) °, with C3--C4--C12 and C7--C6---C11 considerably smaller than 120 ° and • with C4--C12--C13 and C6 C 11--C 10 considerably larger than 120 ° .…”

Section: -Dibenzofurancarboxaldehydementioning

confidence: 59%

“…In conjunction with continuing studies of positional disorder of the type displayed by diben-* To whom correspondence should be addressed. 0108-2701/91 / 102134-04503.00 zofuran (Reppart, Gallucci, Lundstedt & Gerkin, 1984) interest has arisen in the structure of substituted dibenzofurans. This report presents an investigation of crystalline 4-dibenzofurancarboxaldehyde (I), whose structure had not previously been" described.…”

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confidence: 99%

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Structure of 4-dibenzofurancarboxaldehyde, C13H8O2

Fitzgerald¹,

Gallucci²,

Gerkin³

et al. 1991

Acta Crystallogr C

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Mr = 196.21, monoclinic, P2(1)/n, a = 6.589 (1), b = 9.784 (2), c = 14.394 (2) A, beta = 95.69 (1) degrees, V = 923.4 (3) A3, Z = 4, Dx = 1.41 g cm-3, lambda(Mo K alpha) = 0.71073 A, mu = 0.89 cm-1, F(000) = 408, T = 296 K, R = 0.048 for 964 unique reflections having I greater than 3 sigma I. The average C-C bond length within the benzenoid rings in 4-dibenzofurancarboxaldehyde is 1.388 (9) A; the average interior angle is 120.0 (2.6) degrees. While two of the three rings of 4-dibenzofurancarboxaldehyde are planar, the benzenoid ring to which the carbonyl group is attached is slightly non-planar. The dihedral angle between the two benzenoid rings measures 1.4(1) degrees. The structure is composed of pairs of 4-dibenzofurancarboxaldehyde molecules related by inversion centers. This structure is further characterized by approaches of both the carbonyl and the furan O atoms to ring H atoms with separations which are slightly less than the sum of the relevant van der Waals radii.

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Section: -Dibenzofurancarboxaldehydementioning

confidence: 59%

mentioning

confidence: 99%

Structure of 4-dibenzofurancarboxaldehyde, C13H8O2

Fitzgerald¹,

Gallucci²,

Gerkin³

et al. 1991

Acta Crystallogr C

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“…The structures of dibenzofuran (Reppart, Gallucci, Lundstedt & Gerkin, 1984) and dibenzofuran-d8 (Fitzgerald, Gallucci & Gerkin, 1993) were found to manifest a type of disorder such that approximately 10% of the molecules adopted an alternative orientation. This alternative orientation is such that disordered molecules are related to ordered molecules by a 180 ° rotation about an axis passing through the molecular center of mass and perpendicular to the furan ring.…”

Section: Commentmentioning

confidence: 99%

Structure of diphenanthro[1,2-b;2',1'-d]furan at 191 K

Fitzgerald¹,

Gerkin²,

Wei³

et al. 1993

Acta Crystallogr C

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Diphenanthro[1,2-b;2',1'-d]furan crystallizes in space group Pnma (No. 62) with the mirror plane bisecting the molecule and passing through the furan O atom. Although exhibiting packing similar to that of dibenzofuran, this diphenanthrofuran showed no disorder of the sort found in that close molecular analog. The C atoms of the individual phenanthrene rings of the title compound have a mean deviation of 0.027 (21) A from the best least-squares plane describing the rings. The configuration and conformation of the individual phenanthrene rings in this diphenanthrofuran closely match the theoretical and experimental results for phenanthrene itself. Overall, this diphenanthrofuran molecule adopts a distinct V shape, the dihedral angle between the least-squares best-fit planes of the phenanthrene rings being 11.0 (1.2) degrees.

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“…and fluorene: molecules consisting of three rings, were studied calorimetrically by Chirico et al (3) and Finke et al, (4) and were reported to show a phase transition accompanying a heat-capacity jump at T1290 K. They added, in the case of dibenzofuran, the statement that, at Tq260 K, the equilibration times increased to 2 h near T=270 K, 5 h near T=280 K, and to greater than 48 h near T=290 K. Meanwhile, Reppart et al (5) reported from a room-temperature X-ray-diffraction study of dibenzofuran that the molecules were disordered with an alternative orientation only of 9 per cent, and that the two orientations were related to each other by a rotation through p about the axis which passed through the center of mass and was perpendicular to the furan ring. The reorientation proceeds naturally by surmounting a certain energy barrier as a classical process.…”

Section: Introductionmentioning

confidence: 96%