The crystal structure of the azulene,<i>s</i>-trinitrobenzene complex

Hanson, A. W.

doi:10.1107/s0365110x65002700

Cited by 114 publications

(64 citation statements)

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“…The value of 1.463 ,/k measured for the C(1)-C(2) bond is close to that expected for a C(sp2)-C(sp 2) single bond (1.47-1.48 /~,-) (Sutton, 1965). This is a common feature of the tropolonates and tropolones (Karlsson, Pilotti & Wiehager, 1976) and is also observed in systems such as azulene (Hanson, 1965;Ammon & Sundaralingam, 1966) and an amino-imino-cycloheptatriene (Goldstein & Trueblood, 1967) containing ten z~-electrons. The observed C-O bond lengths agree with those found in other metal tropolonates (1.27-1.29 A).…”

Section: Discussionmentioning

confidence: 99%

Bis(tropolonato)copper(II)

Berg¹,

Pilotti²,

Söderholm³

et al. 1978

Acta Crystallogr Sect B

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Section: Discussionmentioning

confidence: 99%

Bis(tropolonato)copper(II)

Berg¹,

Pilotti²,

Söderholm³

et al. 1978

Acta Crystallogr Sect B

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“…6. The orientations of the benzene ring in picryl bromide and the fivemembered ring in fluoranthene resemble those in the azulene:TNB (Hanson, 1965), skatole:TNB and indole:TNB (Hanson, 1964) molecular compounds. This suggests that the M ulliken overlap and orientation principle holds for all these molecular compounds.…”

Section: Discussionmentioning

confidence: 99%

Molecular compounds and complexes. V. Crystallography of equimolar aromatic hydrocarbon:l-X-2,4,6-trinitrobenzene molecular compounds. Crystal structure of fluoranthene: picryl bromide, polymorph I

Herbstein¹,

Kaftory²

1975

Acta Crystallogr Sect B

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Crystal data are reported for the binary n-molecular compounds with naphthalene, anthracene, phenanthrene, acenaphthene, fluoranthene, pyrene or triphenylene as donor and 1,3,5-trinitrobenzene, picric acid, picryl chloride or picryl bromide as acceptor (33 different crystals have been studied). In three out of seven pairs, the trinitrobenzene and picric acid molecular compounds of a particular hydrocarbon are isomorphous, and in four out of seven pairs the picryl chloride and picryl bromide molecular compounds are isomorphous. The structure of fluoranthene:picryl bromide, polymorph I [monoclinic; a=7.664(8), b=8.035 (2), c=31-631 (8)/~,, fl=91-8 (1) °, space group P21/c, Z=4] has been solved by Patterson and Fourier methods and refined by block-diagonal least-squares calculations to a final R of 0.062. The structure consists of quasi-hexagonally close-packed mixed stacks of alternating donor and acceptor molecules. The stack axes are parallel to [100]. The interplanar spacing is 3.49 A, suggesting a rather weak charge-transfer interaction.

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“…A review of gas-phase electron diffraction studies has led to the conclusion that the s-trans (or antiplanar) conformation is favoured for sterically unhindered compounds at normal temperatures (Bohn, 1977), and this is also the case in almost half of the a,fl-unsaturated acids for which crystal structures have been scrutinized (Einspahr & Donohue, 1973). Nevertheless, the s-cis conformation occurs in the majority of cases, especially in cinnamoyl compounds (see, for example, Hanson, 1975). In the present case there seems to be no obvious steric reason for the preference, and, in the absence of through conjugation, no strong electrostatic interaction either.…”

Section: C30h27no6mentioning

confidence: 68%

trans-Cinnamoyl peroxide, C18H14O4

Bethell¹,

Chadwick²,

Maling³

et al. 1984

Acta Crystallogr C

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Introduction. The structure of the title compound (1) was determined in continuation of our programme of work to relate diacyl peroxide structure and rates of thermolysis in solution and also to assist in the interpretation of polarized NMR spectra (CIDNP) by providing geometric data from which electron-nuclear hyperfine coupling constants in the related styryl radical might be estimated.~O~o~ (1) Experimental. (1) (2) 2506 (8) 3511 (22) 1541 (26) 75 (10) C (3) 2755 (14) 2935 (26) 3306 (39) 37 (15) C (4) 2247 (12) 2342 (30) 5287 (34) 64 (14) C (5) 1345 (14) 2257 (26) 5076 (30) 61 (14) C (6) 742 (14) 1587 (27) 6844 (34) 63 (14) C (7) -182 (15) 1658 (28) 6240 (31) 73 (17) C (8) -774 (12) 994 (30) 7649 (39) 68 (15) C (9) -461 (16) 311 (31) 9546 (41) 72 (17) C (10) 435 (20) 186 (28) 10177 (36) 77 (17) C (11) 1040 (13) 908 (28) 8789 (34) 64 (14) O (12) 4247 (7) 3100 (21) 2140 (22) 62 (9) O (13) 3879 (9) 1083 (23) 186 (25) 72 (10) C (14) 4332 (12) 2093 (33) 384 (37) 57 (14) C (15) 5103 (11) 2546 (27) -967 (31) 54 (13) C (16) 5343 (12) 1809 (26) -2761 (31) 55 (13) C (17) 6099 (12) 2022 (26 . C~H,201). Discussion. 1 and 2 respectively, and the atomic numbering, bond lengths, bond angles and torsion angles (not involving H) are in Fig. 3.The molecule adopts an extended conformation in the crystal with the two cinnamoyl moieties essentially planar; the mean angles between the nodal planes of the carbonyl and phenyl groups in the two halves of the molecule are 4.5 and 11.5 o. The two cinnamoyl groups lie in roughly orthogonal planes, however, since the We call attention to two other features of the present structure, namely the bond lengths in and the conformation of the a,fl-unsaturated acyloxy groups. The carbonyl bond length is substantially shorter [mean value 1.15 (2)A] than the average for the 13 compounds containing the cinnamoyl moiety for which structures having R < 0.10 are available [ 1.228 (25) A]. On the other hand it is little less than the average for the eight diacyl peroxides [1.186 (28)/~] which is itself less than is typical for unconjugated acyloxy groups [1.212 (4) .A] (Allen, 1981). The C=C bond lengths are close to the average for a cinnamoyl group. The overall picture is thus of strong conjugative interaction between the phenyl groups and their adjacent C--C bonds, but there seems to be little extension of the conjugation to the carbonyl groups despite the planarity.In trans-cinnamoyl peroxide the aft-unsaturated carbonyl group adopts the s-cis conformation. A review of gas-phase electron diffraction studies has led to the conclusion that the s-trans (or antiplanar) conformation is favoured for sterically unhindered compounds at normal temperatures (Bohn, 1977), and this is also the case in almost half of the a,fl-unsaturated acids for which crystal structures have been scrutinized (Einspahr & Donohue, 1973). Nevertheless, the s-cis conformation occurs in the majority of cases, especially in cinnamoyl compounds (see, for example, Hanson, 1975). In the present case there seems to be no obviou...

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The crystal structure of the azulene,s-trinitrobenzene complex

Cited by 114 publications

References 1 publication

Bis(tropolonato)copper(II)

Bis(tropolonato)copper(II)

Molecular compounds and complexes. V. Crystallography of equimolar aromatic hydrocarbon:l-X-2,4,6-trinitrobenzene molecular compounds. Crystal structure of fluoranthene: picryl bromide, polymorph I

trans-Cinnamoyl peroxide, C18H14O4

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