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Crystal structure of the cage derivative penta-cyclo-[5.4.0.0(2,6).0(3,10).0(5,9)]undeca-8,11-dione ethyl-ene di-thio-ketal.

ABSTRACT: The title penta-cyclo-undecane cage derivative, C13H14OS2, was identified during a thio-ketalization reaction. The reaction selectively gave the title compound and the product corresponding to bis-ketal was not formed. The title compound exhibits unusual Csp (3)-Csp (3) single bond lengths ranging from 1.495?(3) to 1.581?(2) and strained bond angles as small as 89.29?(12) and as large as 115.11?(11)°.

SUBMITTER: Kotha S

PROVIDER: S-EPMC4257192 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature

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Crystal structure of the cage derivative penta-cyclo-[5.4.0.0(2,6).0(3,10).0(5,9)]undeca-8,11-dione ethyl-ene di-thio-ketal.

Kotha Sambasivarao S Sreenivasachary Nampalli N Deodhar Deepak D Shaikh Mobin M

Acta crystallographica. Section E, Structure reports online 20140924 Pt 10

The title penta-cyclo-undecane cage derivative, C13H14OS2, was identified during a thio-ketalization reaction. The reaction selectively gave the title compound and the product corresponding to bis-ketal was not formed. The title compound exhibits unusual Csp (3)-Csp (3) single bond lengths ranging from 1.495 (3) to 1.581 (2) and strained bond angles as small as 89.29 (12) and as large as 115.11 (11)°. ...[more]

PMID: 25484664

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

1,7-Dimethyl-penta-cyclo-[5.4.0.0.0.0]undecane-8,11-dione.

Project description:The structure of the title compound, C(13)H(14)O(2), a penta-cyclo-undecane cage derivative, exhibits unusual Csp(3)-Csp(3) single-bond lengths ranging from 1.505?(3) to 1.607?(2)?Å and strained bond angles as small as 88.7?(1)° and as large as 121.0?(2)°. In this meso compound, an inter-nal non-crystallographic mirror plane exists, bis-ecting the mol-ecule. In the crystal, weak C-H?O hydrogen bonds link the mol-ecules into an infinite spiral about a twofold screw axis along the [100] direction.

| S-EPMC3007444 | biostudies-literature

4,5,7,8,17-Penta-hydr-oxy-14,18-dimethyl-6-methyl-ene-3,10-dioxapenta-cyclo-[9.8.0.0.0.0]nona-dec-14-ene-9,16-dione methanol solvate dihydrate.

Project description:The title quassinoid compound, C(20)H(24)O(9)·CH(3)OH·2H(2)O, is a natural eurycomanone isolated from the roots of Eurycoma longifolia. The mol-ecules contain a fused five-ring system, with one tetra-hydro-furan ring adopting an envelope conformation, one tetra-hydro-pyran-2-one ring in a screw boat conformation, one cyclo-hexenone ring in a half-chair conformation and two cyclo-hexane rings in chair conformations. Intra-molecular C-H⋯O inter-actions generate S(5) ring motifs and an O-H⋯O inter-action generates an S(7) ring motif. In the crystal, mol-ecules are linked via inter-molecular O-H⋯O inter-actions along the b axis and further stacked along a axis. The absolute configuration of the title compound was inferred from previously solved structures of its analogues.

| S-EPMC2968991 | biostudies-literature

14-Bromo-12-chloro-2,16-dioxa-penta-cyclo-[7.7.5.0(1,21).0(3,8).0(10,15)]henicosa-3(8),10,12,14-tetra-ene-7,20-dione.

Project description:In the title compound, C19H16BrClO4, both the fused xanthene rings and one of the cyclo-hexane rings adopt envelope conformations, while the other cyclo-hexane ring is in a chair conformation. In the crystal, mol-ecules are linked by C-H?O hydrogen bonds, forming infinite chains running along [10-1] incorporating R 2 (2)(16) ring motifs. In addition, C-H?? inter-actions and weak ?-? stacking inter-actions [centroid-centroid distance = 3.768?(3)?Å] help to consolidate the packing.

| S-EPMC3648294 | biostudies-literature

3,22-Dioxa-11,14-di-aza-penta-cyclo-[12.8.0.0(2,11).0(5,10).0(15,20)]docosa-5(10),6,8,15(20),16,18-hexa-ene-4,21-dione.

Project description:In the title compound, C18H14N2O4, the piperazine ring adopts a chair conformation and the dihedral angle between the aromatic rings is 13.09?(9)°. In the crystal, mol-ecules are linked along the c axis by C-H?? and N?? [H(N)-centroid distances = 2.8030?(2) and 3.376?(2)?Å] inter-actions between neighbouring mol-ecules.

| S-EPMC3790403 | biostudies-literature

(±)-4,12,15,18,26-Penta-hydroxy-13,17-dioxahepta-cyclo-[14.10.0.0(3,14).0(4,12).0(6,11).0(18,26).0(19,24)]hexa-cosa-1,3(14),6(11),7,9,15,19,21,23-nona-ene-5,25-dione methanol disolvate.

Project description:The title compound, C24H14O9·2CH3OH, displays a chair-shaped form. The two di-hydro-indenone ring systems are located above and below the central fused-ring system, the dihedral angles between the mean planes of di-hydro-indenone ring systems and the mean plane of central fused-ring system are 67.91?(5) and 73.52?(4)°, respectively. In the crystal, extensive O-H?O hydrogen bonds, weak C-H?O hydrogen bonds and C-H?? inter-actions link the mol-ecules into a three-dimensional supra-molecular architecture.

| S-EPMC4011206 | biostudies-literature

(2RS,3SR,10SR,11RS)-3,10-Diphen-oxy-18,21-dioxa-5,8-diaza-penta-cyclo-[20.4.0.0.0.0]hexa-cosa-1(26),12,14,16,22,24-hexa-ene-4,9-dione ethyl acetate hemisolvate.

Project description:In the title compound, C(34)H(30)N(2)O(6)·0.5C(4)H(8)O(2), there are two mol-ecules in the asymmetric unit and the structure is stabilized by C-H?O inter-actions. The two nonsolvent mol-ecules of the asymmetric unit are linked together by a weak C-H?O hydrogen bond. The ethyl acetate mol-ecule is present as a space filler and does not participate in the hydrogen-bonding network.

| S-EPMC3213633 | biostudies-literature

2,4-Dioxa-?(6)-thia-tetra-cyclo-[5.3.1.1(5,9).0(1,5)]dodecane-3,3-dione.

Project description:The crystal structure of the title compound, C(9)H(12)O(4)S, was determined in order to investigate the effect of the eclipsed O atoms on the bond length of the vicinal quaternary C atoms. The two quaternary C atoms of the noradamantane skeleton and the two O atoms to which they are connected all located essentially in the same plane (maximum deviation = 0.01?Å), resulting in an eclipsed conformation of the C-O bonds. The C-C bond of the quaternary C atoms is 1.581?(3)?Å, considerably longer than the other C-C bonds of the mol-ecule due to the stretch of the cage structure.

| S-EPMC3379310 | 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

8-(Biphenyl-4-yl)-8-hydroxy-penta-cyclo-[5.4.0.0.0.0]undecan-11-one ethyl-ene ketal.

Project description:The title compound, C(25)H(24)O(3), synthesized as a potential chiral catalyst, exhibits a range of C-C bond lengths in the penta-cyclo-undecane cage between 1.5144?(18) and 1.5856?(16)?Å. The two benzene rings are not planar with respect to each other, but rather are twisted at a torsion angle of 34.67?(17)°. The mol-ecule has an intra-molecular O-H?O inter-action and participates in two C-H?O inter-molecular inter-actions to form a one-dimensional chain.

| S-EPMC2915336 | biostudies-other

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