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Endo,endo-Tetra-cyclo-[6.2.1.1(3,6).0(2,7)]dodeca-9-en-anti-11-yl 4-bromo-benzoate.

ABSTRACT: The title compound 1-OPBB, C(19)H(19)BrO(2), contains a dechlorinated and hydrogenated isodrin backbone with an anti-4-bromo-benzoate substituent at one of the methano bridges. The dihedral angle between the CO(2) ester plane and the benzene ring plane is 8.5?(2)°. In the crystal, the ester groups stack over benzene rings: the mol-ecules pack as conformational enanti-omers, with nearest parallel benzene ring planes separated by a perpendicular distance of 3.339?(1)?Å. The nearest benzene-ring centroids are 5.266?(1)?Å apart. Possible structural correlation with enhanced solvolytic reactivity is investigated.

SUBMITTER: Lloyd BA

PROVIDER: S-EPMC3569263 | biostudies-literature | 2013 Feb

REPOSITORIES: biostudies-literature

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endo,endo-Tetra-cyclo-[6.2.1.1(3,6).0(2,7)]dodeca-9-en-anti-11-yl 4-bromo-benzoate.

Lloyd Barry A BA Arif Atta M AM Coots Robert J RJ

Acta crystallographica. Section E, Structure reports online 20130109 Pt 2

The title compound 1-OPBB, C(19)H(19)BrO(2), contains a dechlorinated and hydrogenated isodrin backbone with an anti-4-bromo-benzoate substituent at one of the methano bridges. The dihedral angle between the CO(2) ester plane and the benzene ring plane is 8.5 (2)°. In the crystal, the ester groups stack over benzene rings: the mol-ecules pack as conformational enanti-omers, with nearest parallel benzene ring planes separated by a perpendicular distance of 3.339 (1) Å. The nearest benzene-ring ce ...[more]

PMID: 23424486

Similar Datasets

Crystal structures of 3,6-di-allyl-tetra-cyclo[6.3.0.0(4,11).0(5,9)]undeca-2,7-dione and 1,7-di-allyl-penta-cyclo-[5.4.0.0(2,6). 0(3,10).0(5,9)]undecane-8,11-dione: allyl-ated caged compounds.

Project description:The title compounds, C17H20O2 (1) and C17H18O2 (2), are allyl-ated caged compounds. In (1), the carbon atoms bearing the allyl groups are far apart [2.9417?(17)?Å], hence the expected ring-closing metathesis (RCM) protocol failed to give a ring-closing product. When these carbon atoms are connected by a C-C bond as in (2), the distance between them is much smaller [1.611?(3)?Å] and consequently the RCM process was successful. The caged carbon skeleton of (1) can be described as a fusion of four five-membered rings and one six-membered ring. All four five-membered rings exhibit envelope conformations. The structure of compound (2) consists of four five-membered rings, of which two are cyclo-penta-none rings bonded at the 2, 4 and 5 positions and linked at the 3-carbons by a methyl-ene bridge. It also consists of one four-membered and two six-membered rings. All four five-membered rings adopt envelope conformations. In the crystal of (1), mol-ecules are linked via C-H?O hydrogen bonds, forming sheets lying parallel to (010). In the crystal of (2), mol-ecules are linked via C-H?O hydrogen bonds forming chains along [100].

| S-EPMC4257271 | biostudies-literature

5-Bromo-3-cyclo-pentyl-sulfinyl-2,7-dimethyl-1-benzofuran.

Project description:In the title compound, C(15)H(17)BrO(2)S, the cyclo-pentyl ring adopts an envelope conformation. In the crystal, mol-ecules are linked by weak C-H?O hydrogen bonds. A slipped ?-? inter-action occurs between the furan and benzene rings of adjacent mol-ecules [centroid-centroid distance = 3.892?(3)?Å and slippage = 1.786?(3)?Å]. The crystal structure also exhibits a weak C-Br?? [2.919?(3)?Å] inter-action.

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16-Oxa-penta-cyclo-[6.6.5.0(1,18).0(2,7).0(9,14)]nona-deca-2,4,6,9,11,13,18-heptaen-15-one.

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Bicyclo-[2.2.1]hept-2-en-7-yl 4-bromo-benzoate.

Project description:The structure of the title compound, C(14)H(13)BrO(2), which contains a norbornenyl group and a 4-bromo-benzoate ester at the single C-atom bridge, has been redetermined [see McDonald & Trotter (1965 ▶). Acta Cryst.19, 456-463] to modern standards to establish high-precision geometrical data to compare with norbornyl and other tetra-cyclic 4-bromo-benzoates. Possible structural evidence is sought to help explain solvolytic reactivities.

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8-Phenyl-16-thia-penta-cyclo-[6.6.5.0(1,18).0(2,7).0(9,14)]nona-deca-2,4,6,9,11,13,18-hepta-ene.

Project description:In the title compound, C24H18S, the dihedral angles between the phenyl ring and the two benzene rings of the anthracene moiety are 51.92?(9) and 68.24?(9)°, whereas the dihedral angle between the two anthracene benzene rings is 120.13?(9)°. The three non-aromatic six-membered rings are in boat conformations, while the five-membered ring has an envelope conformation on the S atom. In the crystal, there are three C-H?? inter-actions, which facilitate the packing of the mol-ecules.

| S-EPMC3770424 | biostudies-literature

endo-11-(Dibenzyl-amino)-tetra-cyclo-[5.4.0.0.0]undecane-8-one.

Project description:The structure of the title compound, C(25)H(27)NO, is a mono-ketone penta-cyclo-undecane (PCU) mol-ecule bearing a tertiary amine group. One of the methyl-ene groups in the PCU is disordered over two orientations with site-occupancy factors of 0.621 (7) and 0.379 (7).

| S-EPMC3051940 | biostudies-literature

3-(4-Bromo-phen-yl)cyclo-pent-2-en-1-one.

Project description:In the title compound, C11H9BrO, the cyclo-pentenone ring is almost planar with an r.m.s. deviation of 0.0097?Å. The largest inter-ring torsion angles [2.4?(3), 1.3?(3) and 3.53?(2)°] reveal only a very small twist between the rings, and suggest that the two rings are conjugated. The mol-ecule is slightly bowed, as shown by the small dihedral angle between the rings [5.3?(1)°]. The crystal packing pattern consists of parallel sheets that stack parallel to the ac plane. Each sheet consists of mol-ecules that pack side-to-side with the same relative orientation of phenyl and cyclo-pentenone rings along the a- and c-axis directions. Slipped side-to-side, face-to-face and edge-to-face inter-actions exist between pairs of sheets with edge-to-edge and edge-to-face O?H-C(sp (2)) weak hydrogen-bond contacts. A relatively short edge-to-face contact (2.77?Å) also exists between pairs of sheets.

| S-EPMC4051020 | biostudies-literature

5-Bromo-3-cyclo-hexyl-sulfonyl-2,7-dimethyl-1-benzofuran.

Project description:In the title compound, C(16)H(19)BrO(3)S, the cyclo-hexyl ring adopts a chair conformation. In the crystal, mol-ecules are linked through weak C-H?O hydrogen bonds and Br?O contacts [3.211?(1)?Å].

| S-EPMC3089243 | biostudies-other

5-Bromo-3-cyclo-hexyl-sulfinyl-2,7-dimethyl-1-benzofuran.

Project description:In the title compound, C(16)H(19)BrO(2)S, the cyclo-hexyl ring adopts a chair conformation. In the crystal, mol-ecules are linked by a Br?Br [3.5994?(5)?Å] contact and a C-H?? inter-action involving the phenyl ring of the benzofuran. The crystal structure also exhibits a slipped ?-? inter-action between the furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.767?(1)?Å and inter-planar distance of 3.452?(1)?Å with a slippage of 1.508?Å].

| S-EPMC3089368 | biostudies-other

2,9,12,15,18,25,27,34,37,40,43,50-Dodeca-oxa-56-aza-hepta-cyclo-[24.24.5.1(51,55).0(3,8).0(19,24).0(28,33).0(44,49)]hexa-penta-conta-3,5,7,19(24),20,22,28(33),29,31,44,46,48,51,53,55-penta-deca-ene.

Project description:The title compound, C(43)H(45)NO(12), was prepared from the reaction of 2,6-bis-(dibromo-meth-yl)pyridine and bis-phenol in the presence of caesium carbonate as a base. The central ring makes dihedral angles of 64.83?(6), 13.48?(6), 56.96?(6) and 66.21?(6)° with the peripheral rings. In the crystal, mol-ecules are linked by weak C-H?O and C-H?? inter-actions, forming a folded structure.

| S-EPMC3470260 | biostudies-literature

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