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[(2R,5R,6S,9R)-6-Isopropyl-9-methyl-1,4-dioxaspiro-[4.5]decan-2-yl]methyl 4-bromo-benzoate.

ABSTRACT: The title compound, C(20)H(27)BrO(4), a 4-bromo-benzoyl derivative of a stereoisomer of glycerol menthonide, synthesized as part of a study of 3-carbon stereochemical moieties, crystallizes with two crystallographically independent mol-ecules in the asymmetric unit, the two mol-ecules differing only in one of the C-O-C-C torsion angles around the ester O atom [-106.5 (7) and 146.1 (6)°]. The two mol-ecules are crystallographically related by a pseudotranslation along the (011) diagonal of the unit cell, emulating a primitive monoclinic cell of half the volume. The translational symmetry is broken by the 4-bromo-benzoate groups. The crystallographic assignment of the absolute stereochemistry is consistent with having started with (-)-menthone, the acetal C atom is R and the secondary alcohol is R. This brings the bromo-benzoate into approximately the same plane as the menthyl ring and cis to the isopropyl group. The glycerol menthonide sections of the molecules interact with each other via C-H⋯O interactions, leading to the formation of chains either A or B molecules that stretch parallel to [010], forming column-shaped double chains. Interactions between neighboring columns are limited to van der Waals contacts.

SUBMITTER: Kiessling A

PROVIDER: S-EPMC3051951 | biostudies-literature |

REPOSITORIES: biostudies-literature

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(1R,2R,5R,6S,9R,10S,13S,14S,18R)-1,6,7,8,9,14,15,16,17,17,18-Undeca-chloro-penta-cyclo-[12.2.1.1.0.0]octa-deca-7,15-diene.

Project description:The title compound, C(18)H(13)Cl(11), is an undecachlorinated commercial flame retardant. The asymmetric unit contains two independent half-mol-ecules. The complete mol-ecules are generated by crystallographic inversion symmetry, causing the terminal H atoms and one of the Cl atoms to be disordered equally over two sites in each mol-ecule. The central eight-membered rings are in chair-type conformations. In the crystal structure, there is a single weak inter-molecular C-H⋯Cl hydrogen bond.

| S-EPMC2961815 | biostudies-literature

(2S)-2-(3-Oxo-1,4-dioxaspiro-[4.5]decan-2-yl)ethanoic acid.

Project description:The title compound, C(10)H(14)O(5), is an inter-mediate in our study of the asymmetric synthesis of α-hydroxy-alkanoic acids. The structure consists of 1,4-dioxaspiro[4,5]decane skeleton formed when the cyclohexylidene group binds to both of the hydroxyl groups of carboxylic groups of the starting malic acid. The six-membered ring adopts a chair conformation.

| S-EPMC2961159 | biostudies-literature

(5R,6S)-4-Isopropyl-5-methyl-6-phenyl-3-propanoyl-2H-1,3,4-oxadiazinan-2-one.

Project description:The title compound, C(16)H(22)N(2)O(3), was synthesized during the course of a study on (1R,2S)-norephedrine-derived 1,3,4-oxadiazinan-2-ones. The conformation adopted by the isopropyl group is pseudo-axial relative to the oxadiazinan core. The allylic strain contributes to this conformational arrangement.

| S-EPMC2969394 | biostudies-literature

(4R,5R,6S,7R,8S,9R,10S,13S)-7,8β-Epoxy-momilactone-A.

Project description:The title compound, C(20)H(26)O(4), was extracted from Leucas Urticifolia, a wild Lamiaceae herb distributed in the Punjab, Baluchistan, Sindh and the Rajputana desert of Pakistan. The plant is utilized for various medicinal applications by the local community. The title compound is based on the pimarane-diterpene skeleton. The mol-ecule exhibits an ep-oxy ring fused to momilactone-A, leading to a penta-cyclic mol-ecular structure. The absolute configuration was assigned by comparison with the crystal structure of momilactone, but needs further verification. The crystal structure is governed by four inter-molecular hydrogen-bond inter-actions of the C-H⋯O type.

| S-EPMC2961202 | biostudies-literature

6-Benzyl-3-(1,4-dioxaspiro-[4.5]decan-2-yl)-8,8-dimethyl-1-oxa-2,6-diaza-spiro-[4.4]non-2-ene-7,9-dione.

Project description:In the title compound, C(23)H(28)N(2)O(5), the 4,5-dihydro-isoxazole ring adopts a slight envelope conformation and the dioxolane ring is in a twisted conformation. The mol-ecular structure, in the vicinity of the benzyl group, may be influenced by an intra-molecular C-H?O hydrogen bond which generates an S(7) ring motif. In the crystal structure, mol-ecules are linked via weak inter-molecular C-H?O hydrogen bonds, forming extended chains along the b axis. Further stabilization is provided by weak C-H?? inter-actions.

| S-EPMC2971287 | biostudies-literature

8-Methyl-4-morpholinoethyl-1-thia-4-aza-spiro-[4.5]decan-3-one.

Project description:In the title compound, C(15)H(26)N(2)O(2)S, the cyclo-hexane and morpholine rings adopt chair conformations, while the thia-zole ring has a twist conformation. An intra-molecular C-H⋯S hydrogen-bond inter-action forms a five-membered ring. The crystal packing involves C-H⋯O=C inter-molecular inter-actions where carbonyl O atoms act as double acceptors to two symmetrically related H atoms.

| S-EPMC2962192 | biostudies-literature

(1R,4R,5R)-1,3,4-Triphenyl-7-[(R)-1-phenyl-ethyl]-2-oxa-3,7-diaza-spiro-[4.5]decan-10-one.

Project description:In the title compound, C(33)H(32)N(2)O(2), the polysubstituted piperidine ring adopts a chair conformation. The isoxazolidine ring is in an envelope conformation. In the crystal structure, intra- and inter-molecular C-H⋯π inter-actions involving the phenyl rings are observed.

| S-EPMC2915384 | biostudies-literature

2-[(E)-({3-[(E)-(2-Hy-droxy-benzyl-idene)amino-meth-yl]-1,4-dioxaspiro-[4.5]decan-2-yl}meth-yl)imino-meth-yl]phenol.

Project description:In the title compound, C(24)H(28)N(2)O(4), the dioxalane ring has an envelope conformation. The cyclo-hexane ring adopts a chair conformation. The dihedral angle between the benzene rings is 72.5 (3)°. The mol-ecular conformation is stabilized by two intra-molecular O-H⋯N hydrogen-bonding inter-actions with an S(6) graph-set motif. The crystal structure is stabilized by van der Waals inter-actions.

| S-EPMC3394072 | biostudies-literature

(1R,3S,5R,6S)-6-Acet-oxy-8-methyl-3-(p-tolyl-sulfon-yloxy)-8-azoniabicyclo-[3.2.1]octane (2R,3R)-2,3-bis-(benzo-yloxy)-3-carboxy-propanoate.

Project description:The title compound, C(17)H(24)NO(5)S(+)·C(18)H(13)O(8) (-), is the key inter-mediate during the preparation of lesatropane [systematic name (1R,3S,5R,6S)-6-acetoxy-3-(4-methylphenylsulfonyloxy)tropane], a potential anti-glaucoma agent. The tertiary N atom of the tropane ring is involved in inter-molecular N-H⋯O hydrogen bonding, and the carboxylate groups are involved in inter-molecular O-H⋯O hydrogen bonding.

| S-EPMC2977720 | biostudies-literature

(1R,3S,5R,6S)-6-Acet-oxy-3-(4-methyl-phenyl-sulfon-yloxy)tropane.

Project description:IN THE TITLE COMPOUND [SYSTEMATIC NAME: (1R,3S,5R,6S)-8-methyl-3-(4-methyl-phenyl-sulfon-yloxy)-8-aza-bicyclo-[3.2.1]octan-6-yl acetate], C(17)H(23)NO(5)S, the fused piperidine ring exists in a chair conformation with the N atom and one C atom displaced by 0.876 (2) and -0.460 (3) Å, respectively, on opposite sides of the mean plane defined by the other four atoms. The fused pyrrolidine ring adopts an envelope conformation with the N atom deviating by 0.644 (3) Å from the mean plane of the other four atoms.

| S-EPMC2960129 | biostudies-literature

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