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Rac-4,8-Divinyl-bicyclo-[3.3.1]nonane-2,6-dione.

ABSTRACT: The title compound, C(13)H(16)O(2), is a chiral bicyclic structure composed of two fused cyclo-hexa-ne rings possessing both boat and chair conformations. The mol-ecules are packed in enantio-pure columns which are pairwise linked forming an overall racemic solid; within the column pairs the packing is governed by weak dipole-dipole inter-actions stemming from stacked carbonyl functionalities (CO(centroid)-CO(centroid) distance = 3.290?Å).

SUBMITTER: Orentas E

PROVIDER: S-EPMC2969760 | biostudies-literature | 2009 May

REPOSITORIES: biostudies-literature

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rac-4,8-Divinyl-bicyclo-[3.3.1]nonane-2,6-dione.

Orentas Edvinas E Wendt Ola F OF Wärnmark Kenneth K Butkus Eugenijus E Wallentin Carl-Johan CJ

Acta crystallographica. Section E, Structure reports online 20090520 Pt 6

The title compound, C(13)H(16)O(2), is a chiral bicyclic structure composed of two fused cyclo-hexa-ne rings possessing both boat and chair conformations. The mol-ecules are packed in enantio-pure columns which are pairwise linked forming an overall racemic solid; within the column pairs the packing is governed by weak dipole-dipole inter-actions stemming from stacked carbonyl functionalities (CO(centroid)-CO(centroid) distance = 3.290 Å). ...[more]

PMID: 21583208

Similar Datasets

(1R*,2R*,4S*,5R*,6R*,8S*)-4,8-Dimethyl-2,6-diphenyl-bicyclo-[3.3.1]nonane-2,6-diol.

Project description:The racemic title compound, C(23)H(28)O(2), crystallizes in the space group C2/c as a layered structure in which a centrosymmetric three hydrogen bond sequence links four molecules. Both hydroxy groups are involved in this arrangement, but they differ in that one participates in two hydrogen bonds while the other takes part in only one. Between layers, the aromatic rings take part in edge-face interactions [shortest C-H⋯C distances 3.04, 3.10 and 3.12 Å and angle between normal to planes 86.7(2)°], forming a centrosymmetric dimer. The lattice is further stabilized by C-H⋯π interactions involving both methyl (shortest C⋯C 3.82 and 3.97 Å) and methylene (shortest C⋯C 3.60 Å) groups.

| S-EPMC2968924 | biostudies-literature

8-Thia-1,6-diaza-bicyclo-[4.3.0]nonane-7,9-dione.

Project description:There are two independent mol-ecules, A and B, in the asymmetric unit of the title compound, C(6)H(8)N(2)O(2)S. In the crystal, pairs of inter-molecular S?O contacts [3.286?(1)?Å] link the B mol-ecules into inversion dimers.

| S-EPMC3201436 | biostudies-literature

Crystal structures and supra-molecular features of 9,9-dimethyl-3,7-di-aza-bicyclo-[3.3.1]nonane-2,4,6,8-tetra-one, 3,7-di-aza-spiro-[bi-cyclo-[3.3.1]nonane-9,1'-cyclo-penta-ne]-2,4,6,8-tetra-one and 9-methyl-9-phenyl-3,7-di-aza-bicyclo-[3.3.1]nonane-2,4,6,8-tetra-one di-methyl-formamide monosolvate.

Project description:Compounds (I), C9H10N2O4, (II), C11H12N2O4, and (III), C14H12N2O4·C3H7NO represent 9,9-disubstituted-3,7-di-aza-bicyclo-[3.3.1]nonane-2,4,6,8-tetra-one deriv-atives with very similar mol-ecular geometries for the bicyclic framework: the dihedral angle between the planes of the imide groups is 74.87 (6), 73.86 (3) and 74.83 (6)° in (I)-(III), respectively. The dimethyl derivative (I) is positioned on a crystallographic twofold axis and its overall geometry deviates only slightly from idealized C2v symmetry. The spiro-cyclo-pentane derivative (II) and the phen-yl/methyl analog (III) retain only inter-nal Cs symmetry, which in the case of (II) coincides with crystallographic mirror symmetry. The cyclo-pentane moiety in (II) adopts an envelope conformation, with the spiro C atom deviating from the mean plane of the rest of the ring by 0.548 (2) Å. In compound (III), an N-H⋯O hydrogen bond is formed with the di-methyl-formamide solvent mol-ecule. In the crystal, both (I) and (II) form similar zigzag hydrogen-bonded ribbons through double inter-molecular N-H⋯O hydrogen bonds. However, whereas in (I) the ribbons are formed by two trans-arranged O=C-N-H amide fragments, the amide fragments are cis-positioned in (II). The formation of ribbons in (III) is apparently disrupted by participation of one of its N-H groups in hydrogen bonding with the solvent mol-ecule. As a result, the mol-ecules of (III) form zigzag chains rather than the ribbons through inter-molecular N-H⋯O hydrogen bonds. The crystal of (I) was a pseudo-merohedral twin.

| S-EPMC5499299 | biostudies-literature

Acid catalyzed cyclodimerization of 2,2-bis(trifluoromethyl)-4-alkoxy-oxetanes and -thietanes. Synthesis of 2,2,6,6-tetrakis(trifluoromethyl)-4,8-dialkoxy-1,5-dioxocanes and 3,3,7,7-tetrakis(trifluoromethyl)-9-oxa-2,6-dithia-bicyclo[3.3.1]nonane.

Project description:Treatment of 2,2-bis(trifluoromethyl)-4-R-oxetanes (R = C?H?O, n-C?H?O, n-C?H?O) with BF?.OEt? in CH?Cl? solvent results in spontaneous electrophilic [4 + 4] cyclodimerization with the formation of the corresponding 2,2,6,6-tetrakis(trifluoromethyl)-4,8-dialkoxy-1,5-dioxocanes, isolated in 31-42% yield. The structures of two products (R = C?H?O and n-C?H?O) were established by single crystal X-ray diffraction. The corresponding oxetane carrying the bulky t-C?H?O group has different reactivity towards BF?.OEt?, slowly producing a mixture of two acyclic, unsaturated products.Clean and spontaneous reaction with alcohols is another interesting transformation of oxetanes described in this paper. The reaction leads to high yield formation of the corresponding acetals (CF?)?C(OH)CH?CH(OR)OR'.Structurally related 2,2-bis(trifluoromethyl)-4-R-thietanes (R = i-C?H?O, t-C?H?O and C?H?O) have different reactivity towards electrophiles. They are totally inert to the action of BF?.OEt? and rapidly react with a protic acid (H?SO?) forming the same product, 3,3,7,7-tetrakis(trifluoromethyl)-9-oxa-2,6-dithia-bicyclo[3.3.1]nonane in 35-50% yield. The structure of this product was established by single crystal X-ray diffraction.

| S-EPMC2887279 | biostudies-other

6-Formyl-2-naphthyl cis-1,5,7-trimethyl-2,4-dioxo-3-aza-bicyclo-[3.3.1]nonane-7-carboxyl-ate.

Project description:In the title compound, C(23)H(23)NO(5), the C(5)N ring adopts an envelope conformation with a C atom as the flap, whilst the saturated C(6) ring fused to it adopts a chair conformation. In the crystal, inversion dimers linked by pairs of N-H?O hydrogen bonds generate R(2) (2)(8) loops.

| S-EPMC2980281 | biostudies-literature

3-(2,6-Dioxopiperidin-3-yl)-3-aza-bicyclo-[3.2.0]heptane-2,4-dione.

Project description:The title mol-ecule, C(11)H(12)N(2)O(4), consists of a 3-aza-bicyclo-[3.2.0]heptane group containing a nearly planar cyclo-butane ring (r.m.s. deviation of fitted atoms is 0.0609?Å), fused to a pyrrolidine ring, bonded to a 2,6-dioxopiperidine ring at the 3-position. The angle between the mean planes of the cyclo-butane and fused pyrrolidine ring is 67.6?(6)°. The dihedral angles between the mean planes of the pyrrolidine and cyclo-butane rings and the dioxopiperidine ring are 73.9?(2) and 62.4?(4)°, respectively. The pyrrolidine and dioxopiperidine rings are twisted about the 3-yl group [torsion angles = -55.0?(1) and 115.0?(1)°] in a nearly perpendicular manner. Crystal packing is influenced by extensive inter-molecular C-H?O and N-H?O inter-actions between all four carbonyl O atoms and H atoms from the cyclo-butane and dioxopiperidine rings, as well as between the N atom and an H atom from the cyclo-butane ring. In addition, weak ?-ring interactions also occur between H atoms from the cyclobutane ring and the five-membered pyrrolidine ring. As a result, mol-ecules are linked into infinite chains diagonally along the [101] plane of the unit cell in an alternate inverted pattern.

| S-EPMC2968123 | biostudies-literature

2-Isobutyl-2-phosphabicyclo-[3.3.1]nonane 2-selenide.

Project description:The title compound, C(12)H(23)PSe, represents the first structure of a phosphine containing the bicyclic 2-phospha-bicyclo-[3.3.1]nonane (VCH) unit. It contains two chiral centres per mol-ecule which can be either R,R- or S,S and crystallizes as a centrosymmetric, racemic micture of the enanti-omers. The P-Se bond distance of 2.1360?(16)?Å is typical for these compounds. The Tolman cone angle (2.28?Å from P) was calculated as 163°, and the effective cone angle (using the crystallographically determined P-Se bond distance) is 168°.

| S-EPMC2968513 | biostudies-literature

Benzo[1,2-b:4,5-b']dithio-phene-4,8-dione.

Project description:The title mol-ecule, C(10)H(4)O(2)S(2), is situated on a crystallographic center of inversion. In the crystal, weak hydrogen bonding contributes to the packing of the mol-ecules.

| S-EPMC3344548 | biostudies-literature

(1S*,5R*)-9-Phenyl-9-aza-bicyclo-[3.3.1]nonan-3-one.

Project description:In the title compound, C(14)H(17)NO, the piperidinone and piperidine rings both adopt a chair conformation. The chiral crystals were obtained from a racemic reaction product via spontaneous resolution.

| S-EPMC3379287 | biostudies-literature

3-Nitroso-2,4,6,8-tetra-phenyl-3,7-diaza-bicyclo-[3.3.1]nonan-9-one.

Project description:In the title compound, C(31)H(27)N(3)O(2), the two piperidine rings fused to each other each adopt a slightly distorted chair conformation. The phenyl rings on the N-unsubstituted piperidine ring occupy an equatorial position, while those on the N-nitroso-substituted piperidine ring are in axial positions. The NO group is approximately coplanar with the piperidine ring with a maximum deviation of 0.048?(4)?Å. The dihedral angles between the mean planes of the axially and equatorially oriented phenyl rings are 27.7?(1) and 31.9?(1)°, respectively. Mol-ecular packing is stabilized by weak inter-molecular C-H?O and C-H?? inter-actions.

| S-EPMC3152129 | biostudies-literature

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