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Crystal structure of 1,1'-[imidazolidine-1,3-diylbis(methyl-ene)]bis-(naphthalen-2-ol).

ABSTRACT: The crystal structure of the title compound, C25H24N2O2, at 173?K has monoclinic (C2/c) symmetry. The mol-ecule is located on a crystallographic twofold rotation axis with only half a mol-ecule in the asymmetric unit. The imidazolidine ring adopts a twist conformation, with a twist about the ring C-C bond. The crystal structure shows the anti-clinal disposition of the two (2-hy-droxy-naphthalen-1-yl)methyl substituents of the imidazolidine ring. The structure displays two intra-molecular O-H?N hydrogen bonds, each forming an S(6) ring motif.

SUBMITTER: Rivera A

PROVIDER: S-EPMC4350733 | biostudies-literature | 2015 Mar

REPOSITORIES: biostudies-literature

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Crystal structure of 1,1'-[imidazolidine-1,3-diylbis(methyl-ene)]bis-(naphthalen-2-ol).

Rivera Augusto A Rojas Jicli José JJ Ríos-Motta Jaime J Bolte Michael M

Acta crystallographica. Section E, Crystallographic communications 20150207 Pt 3

The crystal structure of the title compound, C25H24N2O2, at 173 K has monoclinic (C2/c) symmetry. The mol-ecule is located on a crystallographic twofold rotation axis with only half a mol-ecule in the asymmetric unit. The imidazolidine ring adopts a twist conformation, with a twist about the ring C-C bond. The crystal structure shows the anti-clinal disposition of the two (2-hy-droxy-naphthalen-1-yl)methyl substituents of the imidazolidine ring. The structure displays two intra-molecular O-H⋯N h ...[more]

PMID: 25844181

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1,1'-[Imidazolidine-1,3-diylbis(methyl-ene)]bis-(1H-benzotriazole).

Project description:In the title compound, C(17)H(18)N(8), the imidazolidine ring adopts an envelope conformation with the substituents at the N atoms in trans positions with respect to the central ring. The dihedral angle between the two benzotriazole rings is 71.65?(10)°. In the crystal, non-classical C-H?N inter-actions link the mol-ecules into helical chains along the b axis. The crystal packing is further stabilized by weak C-H?? inter-actions.

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4,4'-Dimethyl-2,2'-[imidazolidine-1,3-diylbis(methyl-ene)]diphenol.

Project description:The imidazolidine ring in the title compound, C(19)H(24)N(2)O(2), adopts a twist conformation and its mean plane (r.m.s. deviation = 0.19?Å) makes dihedral angles of 72.38?(9) and 71.64?(9)° with the two pendant aromatic rings. The dihedral angle between the phenyl rings is 55.94?(8)°. The mol-ecular structure shows the presence of two intra-molecular O-H?N hydrogen bonds between the phenolic hydroxyl groups and N atoms with graph-set motif S(6). In the crystal, C-H?O hydrogen bonds lead to the formation of chains along the b-axis direction.

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4,4'-Difluoro-2,2'-[imidazolidine-1,3-diylbis(methyl-ene)]diphenol.

Project description:In the title compound, C(17)H(18)F(2)N(2)O(2), the imidazolidine ring system exists in a twist conformation. The mean plane through this ring system forms dihedral angles of 80.8?(8)° and 66.2?(13)°, with the benzene rings. The dihedral angle between the benzene rings is 52.0?(14)°. Two intra-molecular O-H?N hydrogen bonds each generate S(6) ring motifs. In the crystal, weak C-H?O hydrogen bonds form dimers, which are connected by further C-H?O inter-actions.

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2,2'-[Imidazolidine-1,3-diylbis(methyl-ene)]diphenol.

Project description:In the title mol-ecule, C(17)H(20)N(2)O(2), the imidazolidine ring adopts a twist conformation. The mean plane through the five atoms of the imidazolidine ring makes dihedral angles of 70.18?(4) and 74.14?(4)° with the planes of the two aromatic rings. The dihedral angle between the benzene rings is 53.11?(5)°. Both phenol -OH groups form intra-molecular hydrogen bonds to the N atoms, with graph-set motif S(6). In the crystal, pairs of O-H?O hydrogen bonds link the mol-ecules into dimers with R(4) (4)(18) ring motifs. The crystal packing is further stabilized by C-H?O and weak C-H?? inter-actions.

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4,4'-Di-tert-butyl-2,2'-[imidazolidine-1,3-diylbis(methyl-ene)]diphenol.

Project description:In the title compound, C25H36N2O2, the two tert-butyl-substituted benzene rings are inclined at an angle of 53.5?(3)° to one another. The imidazolidine ring has an envelope conformation with with one of the C atoms of the ethylene fragment as the flap. The structure displays two intra-molecular O-H?N hydrogen bonds that generate S(6) ring motifs. The crystal studied was a non-merohedral twin with a fractional contribution of 0.281(6) for the minor domain.

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Project description:The title compound, C(18)H(20)Br(2)N(2)O(2), the heterocyclic ring adopts a chair conformation. The benzene rings make dihedral angles of 86.84?(10) and 60.73?(10)° with the mean plane of the heterocyclic ring. The dihedral angle between the two benzene rings is 79.77?(10)°. The mol-ecular structure is stabilized by two intra-molecular hydrogen bonds between the phenolic hy-droxy groups and N atoms with graph-set motif S(6). The crystal structure is stabilized by weak C-H?? inter-actions.

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Crystal structure of the di-Mannich base 4,4'-di-chloro-3,3',5,5'-tetra-methyl-2,2'-[imidazolidine-1,3-diylbis(methyl-ene)]diphenol.

Project description:The title compound, C21H26Cl2N2O2, was prepared in a solvent-free microwave-assisted synthesis, and crystallizes in the ortho-rhom-bic space group Pna21. The imidazolidine ring adopts an envelope conformation and its mean plane is almost perpendicular to the two pendant aromatic rings [dihedral angles = 84.61?(9) and 86.54?(9)°]. The mol-ecular structure shows the presence of two intra-molecular O-H?N hydrogen bonds between the phenolic hy-droxy groups and imidazolidine N atoms. The two 3-chloro-6-hy-droxy-2,4-di-methyl-benzyl groups are located in a cis orientation with respect to the imidazolidine fragment. As a result, the lone pairs of electrons on the N atoms are presumed to be disposed in a syn conformation. This is therefore the first example of an exception to the 'rabbit-ears' effect in such 2,2'-[imidazolidine-1,3-diylbis(methyl-ene)]diphenol derivatives.

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2,2'-[(4-Methyl-2-phenyl-imidazolidine-1,3-di-yl)bis-(methyl-ene)]diphenol.

Project description:The methyl-substituted imidazolidine ring of the title compound, C24H26N2O2, adopts an envelope conformation with the N atom adjacent to the methyl-ene group as the flap. The meth-yl-ethyl-ene fragment in this ring is disordered over two positions with an occupancy ratio of 0.899?(4):0.101?(4). The hy-droxy-benzyl groups are inclined at 71.57?(15) and 69.97?(19)° to the mean plane of major disorder component of the heterocyclic ring with an inter-planar angle between the two hy-droxy-benzyl groups of 66.00?(5)°. The phenyl substit-uent approaches a nearly perpendicular orientation relative to the mean plane of the imidazolidine ring, making a dihedral angle of 75.60?(12)°. This conformation is stabilized by two intra-molecular O-H?N bonds, which generate S(6) ring motifs.

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1,1'-[(5-Hy-droxy-methyl-1,3-phenyl-ene)bis-(methyl-ene)]dipyridin-4(1H)-one monohydrate.

Project description:The asymmetric unit of the title compound, C(19)H(18)N(2)O(3), comprises a whole organic dipyridinone mol-ecule plus a water mol-ecule of crystallization. The planes of the pyridinone rings are approximately perpendicular with the plane of the central aromatic ring [dihedral angles = 80.68?(8) and 83.65?(8)°]. The C-O bond of the hy-droxy group subtends an angle of 31.71?(10)° with the plane through the central aromatic ring. The crystal packing is mediated by the presence of several O-H?O hydrogen-bonding inter-actions and while the water mol-ecules form a C(2) (1)(4) chain parallel to the c axis of the unit cell, the pendant hy-droxy groups are engaged in O-H?O=C hydrogen bonds described by a C(1) (1)(12) graph-set motif which runs parallel to the a axis.

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2,2'-{[2-(2-Chloro-phen-yl)-4-methyl-imidazolidine-1,3-di-yl]bis-(methyl-ene)}diphenol.

Project description:In the title compound, C24H25ClN2O2, the 2-hy-droxy-benzyl substituents and the 2-chloro-phenyl group occupy the sterically preferred equatorial positions, whereas the methyl group occupies the axial position. The imidazolidine ring adopts an envelope conformation with one of the N atoms adjacent to the methylene group as the flap. The chloro-phenyl substit-uent approaches a nearly perpendicular orientation relative to the mean plane of the imidazolidine ring, making a dihedral angle of 73.44?(12)° and the Cl atom is almost coplanar with the C atom bearing the chloro-phenyl substituent [Cl-C-C-C torsion angle = 1.1?(3)°]. The hy-droxy-benzyl groups make dihedral angles of 71.23?(15) and 69.13?(19)° with the mean plane of the heterocyclic ring. The dihedral angle between the two hy-droxy-benzyl groups is 69.61?(12)°. The mol-ecular structure features two intra-molecular O-H?N hydrogen bonds with graph-set motif S(6) between the phenolic hydroxyl groups and N atoms.

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