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Crystal structure and C-H?F hydrogen bonding in the fluorinated bis-benzoxazine: 3,3'-(ethane-1,2-di-yl)bis-(6-fluoro-3,4-di-hydro-2H-1,3-benzoxazine).

ABSTRACT: The title fluorinated bis-benzoxazine, C₁₈H₁₈F₂N₂O₂, crystallizes with one half-mol-ecule in the asymmetric unit, which is completed by inversion symmetry. The fused oxazine ring adopts an approximately half-chair conformation. The two benzoxazine rings are oriented anti to one another around the central C-C bond. The dominant inter-molecular inter-action in the crystal structure is a C-H?F hydrogen bond between the F atoms and the axial H atoms of the OCH₂N methyl-ene group in the oxazine rings of neighbouring mol-ecules. C-H?? contacts further stabilize the crystal packing.

SUBMITTER: Rivera A

PROVIDER: S-EPMC5050787 | biostudies-literature |

REPOSITORIES: biostudies-literature

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3,3'-(Ethane-1,2-di-yl)bis-(3,4-dihydro-2H-1,3-benzoxazine).

Project description:The title compound, C(18)H(20)N(2)O(2), was prepared by Mannich-type reaction of phenol, ethane-1,2-diamine and formaldehyde. The heterocyclic rings adopt half-chair conformations. The acyclic methyl-ene groups attached to the N atoms are in an axial position. In the crystal, weak C-H?O hydrogen bonds link the mol-ecules into dimers. These dimers are further connected via C-H?? contacts.

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3,3'-(Ethane-1,2-di-yl)bis-(6-methyl-3,4-dihydro-2H-1,3-benzoxazine).

Project description:The asymmetric unit of the title compound, C(20)H(24)N(2)O(2), contains one half-mol-ecule, which is completed by inversion symmetry. In the crystal, mol-ecular chains are formed through non-classical C-H⋯O hydrogen bonds, formed between axial H atoms of the oxazine ring and a O atom of a neighboring mol-ecule.

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3,3'-(Ethane-1,2-diyl)bis(6-meth-oxy-3,4-dihydro-2H-1,3-benzoxazine) mono-hydrate.

Project description:The asymmetric unit of the title compound, C(20)H(24)N(2)O(4)·H(2)O, contains one half-organic mol-ecule (an inversion centre generates the other half of the mol-ecule) and a half-mol-ecule of water (the O atom has site symmetry 2). The near planarity of the fused-benzene ring is illustrated by the very small deviations of all the atoms from the plane [largest deviation = 0.0092 (11) Å. The six-membered N,O-containing ring adopts a half-chair conformation. The observed N-CH(2) and CH(2)-O bond lengths can be correlated to the manifestation of an anomeric effect in the N-CH(2)-O unit. In the crystal, the mol-ecules are connected into zigzag chains parallel to [001] through O-H⋯N hydrogen bonds formed between the oxazinic N atom and the solvent water mol-ecule. The chains are consolidated by C-H⋯O inter-actions.

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C-I⋯N short contacts as tools for the construction of the crystal packing in the crystal structure of 3,3'-(ethane-1,2-di-yl)bis-(6-iodo-3,4-di-hydro-2H-1,3-benzoxazine).

Project description:The asymmetric unit of the title compound, C18H18I2N2O2, consists of one half-mol-ecule, completed by the application of inversion symmetry. The mol-ecule adopts the typical structure for this class of bis-benxozazines, characterized by an anti orientation of the two benzoxazine rings around the central C-C bond. The oxazinic ring adopts a half-chair conformation. In the crystal, mol-ecules are linked by C-I⋯N short contacts [I⋯N = 3.378 (2) Å], generating layers lying parallel to the bc plane.

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Project description:The title compound, C10H13NO2, crystallizes with two crystallographically independent mol-ecules of similar geometry in the asymmetric unit; the six-membered oxazine rings adopts a half-chair conformation. Neither hydrogen bonds nor ?-? inter-actions are observed in the crystal structure.

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3,3'-(p-Phenyl-ene)bis-(3,4-dihydro-2H-1,3-benzoxazine).

Project description:Mol-ecules of the title compound, C(22)H(20)N(2)O(2), are situated on crystallographic centres of symmetry. The oxazinane ring adopts a sofa conformation. Mol-ecules are linked into cyclic centrosymmetric dimers via C-H?O hydrogen bonds with the motif R(2) (2)(6). In addition to the C-H?O inter-actions, the crystal structure is also stabilized by C-H?? inter-actions.

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3,3'-(Ethane-1,2-di-yl)bis-(2-thioxo-1,3-oxazolidin-4-one).

Project description:The asymmetric unit of the title compound, C(8)H(8)N(2)O(4)S(2), contains one half of a centrosymmetric mol-ecule. A short C⋯O distance of 3.012 (4) Å between the carbonyl groups of neighbouring mol-ecules indicates the presence of dipole-dipole inter-actions. The crystal packing exhibits also weak inter-molecular O⋯S [3.239 (3) Å] and C-H⋯O inter-actions.

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(E)-3,3'-(Diazene-1,2-di-yl)bis-(1-methyl-1,4,5,6-tetra-hydro-pyrrolo-[3,4-c]pyrazol-5-ium) dinitrate dihydrate.

Project description:The title compound, C(12)H(18)N(8) (2+)·2NO(3) (-)·2H(2)O, was synthesized unexpectedly from 3-amino-1-methyl-1,4,5,6-tetra-hydro-pyrrolo-[3,4-c]pyrazol-5-ium chloride and cerium(IV) ammonium nitrate. The cation has a crystallographically imposed centre of symmetry. In the crystal, the ions and water mol-ecules are linked via O-H?N, N-H?O and O-H?O hydrogen bonds into a three-dimensional network.

| S-EPMC3254494 | biostudies-literature

3,3'-Ethyl-enebis(3,4-dihydro-6-chloro-2H-1,3-benzoxazine).

Project description:The asymmetric unit of the title compound, C(18)H(18)Cl(2)N(2)O(2), contains one half of an independent mol-ecule, the other half being generated via a centre of inversion at the mol-ecular centroid. In the crystal structure, mol-ecular chains are formed through non-classical C-H? O hydrogen bonds between an axial H atom of the oxazine ring and the O atom of a neighbouring mol-ecule.

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3,3'-Dimethyl-1,1'-(butane-1,4-di-yl)diimidazolium bis-(tetra-fluoro-borate).

Project description:The title compound, C(12)H(20)N(4) (2+)·2BF(4) (-), was prepared by the anion exchange of a dibromide ionic liquid with sodium tetra-fluoro-borate. The asymmetric unit contains one half of the imidazolium cation, which lies about an inversion centre at the mid-point of the central C-C bond of the linking butyl chain. The two planar imidazole rings (r.m.s. deviation = 0.0013?Å) are strictly parallel and separated by 2.625?(7)?Å [vertical distance between the centroids of two imidazole rings], giving the mol-ecule a stepped appearance. In the crystal structure, inter-molecular C-H?F hydrogen bonds link the cations and anions, generating a three-dimensional network.

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