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16α-Bromo-17β-hydr-oxy-5α-androstan-3β-yl acetate.

ABSTRACT: The title compound, C(21)H(33)BrO(3), an inter-mediate in the synthesis of the neuromuscular blocking agent rocuronium bromide, contains two independent mol-ecules in the asymmetric unit, which have almost identical geometries: in both mol-ecules, the steroidal rings A, B and C have slightly flattened chair conformations and ring D assumes a half-chair conformation. In the crystal, O-H⋯O hydrogen bonds and weak C-H⋯O and C-H⋯Br inter-actions help to establish the packing.

SUBMITTER: Shi R

PROVIDER: S-EPMC2983941 | biostudies-literature |

REPOSITORIES: biostudies-literature

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3α,4α-Ep-oxy-5α-androstan-17β-yl acetate.

Project description:The title compound, C(21)H(32)O(3), results from modifications of the A and D rings of the aromatase substrate androstenedione. Ring A adopts a conformation between 10β-sofa and 1α,10β half-chair. Rings B and C are in slightly flattened chair conformations. Ring D approaches a 13β-envelope conformation, probably due to the acet-oxy substituent, and shows a very short Csp(3)-Csp(3) bond next to the epoxide ring, which is characteristic of 3-4 epoxides. .

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5α-Androst-3-en-17β-yl acetate.

Project description:In the crystal structure of the title compound, C(21)H(32)O(2), ring A is highly distorted, with a conformation inter-mediate between 10β-sofa and 1α,10β-half chair; rings B and C have slightly flattened chair conformations. Ring D assumes an unusual 13β-envelope conformation, probably induced by the acet-oxy substituent. Cohesion of the crystal structure is due only to weak van der Waals inter-actions.

| S-EPMC2979999 | biostudies-literature

Androstane-3β,5α,6β,17β-tetrol tri-hydrate.

Project description:The title hydrated tetrol, C(19)H(32)O(4)·3H(2)O, was synthesized by stereoselective reduction of the compound 3β,5α,6β-trihy-droxy-androstan-17-one. All rings are fused trans. The organic mol-ecules are connected head-to-tail along the c axis via O-H⋯O hydrogen bonds. Layers of water mol-ecules in the ab plane inter-connect these chains. A quantum chemical ab initio Roothan Hartree-Fock calculation of the isolated mol-ecule gives values for the mol-ecular geometry close to experimentally determined ones, apart from the C-O bond lengths, whose calculated values are significantly smaller than the measured ones, probably a consequence of the involvement of the C-OH groups in the hydrogen-bonding network.

| S-EPMC3151997 | biostudies-literature

rac-N-{6-[Bromo-(hydr-oxy)meth-yl]-2-pyrid-yl}pivalamide.

Project description:The title compound, C(11)H(15)BrN(2)O(2), contains an amide group which is close to coplanar with the adjacent pyridine ring, the dihedral angle between the planes being 9.0?(5)°. The mol-ecular packing reveals a mutual hydrogen-bond inter-action between centrosymmetrically related hydroxyl O atoms. Further hydrogen bonding involving O-H?Br and N-H?Br inter-actions also appears to consolidate the packing.

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6?-Chloro-5?-hydr-oxy-20-oxopregnan-3?-yl acetate.

Project description:The title steroid, C(23)H(35)ClO(4), is a pregnane derivative prepared by ring opening of the corresponding 5?,6?-ep-oxy steroid with BiCl(3). There are two symmetry-independent mol-ecules in the asymmetric unit that show no significant differences concerning bond lengths and angles. The conformation of the six-membered rings in both mol-ecules is close to a chair form, while the five-membered ring adopts an envelope conformation. All rings in both mol-ecules are trans-fused. The mol-ecules are held together by an extensive O-H?O hydrogen-bonding network.

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1-(5-Bromo-2-hydr-oxy-4-methoxy-phen-yl)ethanone.

Project description:In the title compound, C(9)H(9)BrO(3), the dihedral angle between the ethanone group and the aromatic ring is 3.6?(2)°. The mol-ecular conformation is consolidated by an intra-molecular O-H?O hydrogen bond. The crystal structure is stabilized by ?-? inter-actions between the benzene rings [centroid-centroid distance = 3.588?(2)?Å].

| S-EPMC2977251 | biostudies-literature

16?,17?-Ep-oxy-5?-hydr-oxy-6?-nitrooxy-20-oxopregnan-3?-yl acetate.

Project description:The title steroid, C(23)H(33)NO(8), is a pregnane derivative obtained regio-, stereo- and chemoselectively from the ring opening of the corresponding 5?,6?;16?,17?-diepoxide with bis-muth(III) nitrate. There are two symmetry-independent mol-ecules in the asymmetric unit that show no significant differences concerning bond lengths and angles. All rings are trans-fused. The conformations of the six-membered rings are close to chair forms, while the five-membered ring adopts an envelope conformation. The mol-ecules are held together by an extensive O-H?O hydrogen-bonding network of chains runnning along the a axis.

| S-EPMC2969566 | biostudies-literature

2,2'-Bis(9-hydr-oxy-9-fluoren-yl)biphen-yl-ethyl acetate (1/1).

Project description:In the title host-guest compound, C(38)H(26)O(2)·C(4)H(8)O(2), the ethyl acetate mol-ecule (guest), which adopts a fully extended conformation, and the biphenyl derivative (host) are connected via O-H?O hydrogen bonds [H?O = 1.90?(3)?Å] into discrete assemblies. The hydro-carbon skeleton of the host mol-ecule deviates only slightly from C(2) symmetry. The OH groups of the host are involved in intra-molecular O-H?O hydrogen bonding [H?O = 1.83?(3)?Å].

| S-EPMC2962236 | biostudies-literature

Ethyl [1-(4-bromo-phen-yl)-1-hydr-oxy-3-oxobut-yl](phen-yl)phosphinate monohydrate.

Project description:In the title hydrate, C(18)H(20)BrO(4)P·H(2)O, a staggered conformation is found when the organic mol-ecule is viewed down the central P-C bond, with the oxo and hydroxyl groups being diagonally opposite; each of the central P and C atoms has an S-configuration. The crystal structure features supra-molecular double chains along the b axis mediated by O(hydrox-yl)-H?O(oxo), O(water)-H?O(oxo), and O(water)-H?O(water) hydrogen bonds.

| S-EPMC2983684 | biostudies-literature

3-Hydr-oxy-4-nitro-phenyl acetate.

Project description:In the mol-ecule of the title compound, C(8)H(7)NO(5), the acetate group is oriented with respect to the aromatic ring at a dihedral angle of 85.30 (3)°. An intra-molecular O-H⋯O hydrogen bond results in the formation of a non-planar six-membered ring, adopting an envelope conformation. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules.

| S-EPMC2967961 | biostudies-literature

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