Crystal structure of 1,2-bis(6-bromo-3,4-dihydro-2H-benz[e][1,3]oxazin-3-yl)ethane: a bromine-containing bis-benzoxazine
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چکیده
The title benzoxazine molecule, C18H18Br2N2O2, was prepared by a Mannich-type reaction of 4-bromo-phenol with ethane-1,2-di-amine and formaldehyde. The title compound crystallizes in the monoclinic space group C2/c with a centre of inversion located at the mid-point of the C-C bond of the central CH2CH2 spacer. The oxazinic ring adopts a half-chair conformation. The structure is compared to those of other functionalized benzoxazines synthesized in our laboratory. In the crystal, weak C-H⋯Br and C-H⋯O hydrogen bonds stack the mol-ecules along the b-axis direction.
منابع مشابه
Crystal structure and C—H⋯F hydrogen bonding in the fluorinated bis-benzoxazine: 3,3′-(ethane-1,2-diyl)bis(6-fluoro-3,4-dihydro-2H-1,3-benzoxazine)
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 hyd...
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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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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...
متن کامل3,3′-(Ethane-1,2-diyl)bis(3,4-dihydro-2H-1,3-benzoxazine)
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⋯π contacts.
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Diethyl bromomalonate (2) with an equimolar amount of 2-aminophenol (1) in the presence of sodium fluoride undergoes a cyclization reaction to form 2H,4H-2-ethoxycarbonyl-3,4-dihydro-3-oxo-1,4-benzoxazine (3). Furthermore, compound 3 undergoes a condensation reaction with hydrazine hydrate in the presence of methanol to yield 2H,4H-2-hydrazinocarbonyl-3,4-dihydro-3-oxo-1,4-benzoxazine (4), whic...
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