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Crystal structure of 2-{(E)-[(2-hy-droxy-phen-yl)iminium-yl]meth-yl}-4-methyl-phenolate.

ABSTRACT: The title compound, C14H13NO2, exists as a zwitterion in the solid state, with the H atom of the phenol group transferred to the imine N atom. The dihedral angle between the planes of the benzene rings is 10.13?(9)°. Intra-molecular N-H?O hydrogen bond generate S(6) and S(5) loops. In the crystal, mol-ecules are connected by O-H?O hydrogen bonds, generating C(9) chains propagating in the [010] direction.

SUBMITTER: Shalini S

PROVIDER: S-EPMC4420074 | biostudies-literature | 2015 May

REPOSITORIES: biostudies-literature

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(E)-4-Hy-droxy-2-{[(2-phenyl-eth-yl)iminium-yl]meth-yl}phenolate.

Project description:The title Schiff base compound, C(15)H(15)NO(2), crystallized as the iminium-phenolate zwitterion. The H atom is localized on the imine N atom, forming a strong intra-molecular hydrogen bond with the phenolate O atom, and giving rise to an S(6) ring motif. The mol-ecule has an E conformation about the C=N bond. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, forming chains propagating along [010]. There are also C-H⋯O inter-actions present.

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Crystal structure of N-[(2-hy-droxy-naphthalen-1-yl)(4-methyl-phen-yl)meth-yl]acetamide.

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| S-EPMC4438828 | biostudies-literature

5-Hy-droxy-2-{(E)-[(3-nitro-phen-yl)iminio]meth-yl}phenolate.

Project description:The title compound, C(13)H(10)N(2)O(4), crystallized as the zwitterionic tautomer. As a result, the phenolate C-O(-) bond [1.296 (2) Å] is shorter than a normal Csp(2)-O(H) bond, and the azomethine C=N bond [1.314 (2) Å] is longer than a normal C=N double bond. The mol-ecule is nearly planar, the mean plane of the nitro-substituted benzene ring forming dihedral angles of 9.83 (7) and 8.45 (9)° with the other benzene ring and with the nitro group, respectively. The mol-ecular conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond. In the crystal, strong O-H⋯O hydrogen bonds link the mol-ecules into double-stranded chains along the b-axis direction. Within the chains there are π-π interactions involving the benzene rings of adjacent molecules [centroid-centroid distance = 3.669 (1) Å]. The chains are linked via C-H⋯O hydrogen bonds, forming R(2) (1)(6), R(2) (1)(7) and R(2) (2)(10) ring motifs.

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Crystal structure of {[2-hy-droxy-2-(3-meth-oxy-phen-yl)cyclo-hex-yl]meth-yl}di-methyl-ammonium benzoate.

Project description:The title compound, C16H26NO2 (+)·C7H5O2 (-), is a benzoate salt of the painkiller Tramadol. The six-membered cyclo-hexane ring of the cation adopts a slightly distorted chair conformation and carries OH and 3-meth-oxy-phenyl substituents at the 2-position and a protonated methyl-aza-niumylmethyl group at the 3-position. In addition, a weak intra-molecular C-H?O hydrogen bond is observed in the cation. In the crystal, weak O-H?O, N-H?O and C-H?O hydrogen bonds link the components into chains along [010]. A C-H?? contact is also observed.

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(E)-4-Hy-droxy-2-[(2-hy-droxy-phen-yl)iminiometh-yl]phenolate.

Project description:The title compound, C(13)H(11)NO(3), crystallizes in a zwitterionic form and has a trans configuration about the C=N bond. The mol-ecule is almost planar, the dihedral angle between the two benzene rings being 4.32?(8)°. The two hy-droxy substit-uents are coplanar with each of their attached benzene rings [r.m.s. deviations of 0.0053?(2) and 0.0052?(2)?Å]. An intra-molecular N-H?O hydrogen bond formed between the iminium N and the phenolate O atom generates an S(6) ring motif. In the crystal, the mol-ecules are linked through O-H?O hydrogen bonds into chains along [110]. Two neighbouring chains are further connected through O-H?O hydrogen bonds in an anti-parallel manner. ?-? inter-actions are also observed, with centroid-centroid distances of 3.7115?(19) and 3.743?(2)?Å.

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Crystal structure of N-(2-hy-droxy-5-methyl-phen-yl)benzamide.

Project description:In the title compound, C14H13NO2, the mean plane of the non-H atoms of the central amide fragment C-N-C(=O)-C (r.m.s. deviation = 0.029 Å) forms dihedral angles of 5.63 (6) and 10.20 (5)° with the phenyl and hy-droxy-phenyl rings, respectively. A short intra-molecular N-H⋯O contact is present. In the crystal, the mol-ecules are linked by O-H⋯O hydrogen bonds to generate C(7) chains along [100]. The chains are reinforced by weak C-H⋯O contacts, which together with the O-H⋯O bonds lead to R 2 (2)(7) loops. Very weak N-H⋯O inter-actions link the mol-ecules into inversion dimers.

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Crystal structure of (E)-2-[(2-hy-droxy-4-meth-oxy-phen-yl)(phen-yl)methyl-idene]-N-phenyl-hydrazine-1-carboxamide.

Project description:The title compound, C21H19N3O3, has an E conformation about the azomethine double bond. The central moiety of the hydrazinecarboxamide moiety [-N-N-C(=O)-N-] has an almost coplanar arrangement [maximum deviation for the C atom = 0.010 (2) Å]. This central moiety is flanked by three aromatic rings and its mean plane makes dihedral angles of 24.7 (1), 72.91 (12) and 34.26 (11) Å, respectively, with the phenolic ring, the phenyl ring attached to the same C atom as the phenolic ring, and the phenyl-hydrazine ring. The adjacent phenolic and phenyl rings are twisted away from each other to reduce steric hindrance and make a dihedral angle of 80.59 (12)°. The phenolic and phenyl-hydrazine rings are inclined to one another by 28.89 (11)°. The rigidity of the mol-ecule is increased by an intra-molecular O-H⋯N hydrogen bond involving the phenolic hydrogen and the azomethine N atom. In the crystal, the carbonyl O atom forms bifurcated hydrogen bonds with the two NH atoms of the hydrazinic group, leading to the formation of chains propagating along [001]. Within the chains there are also C-H⋯O hydrogen bonds present. The chains are linked via C=O⋯π [3.4316 (18) Å] and parallel slipped π-π inter-actions, involving inversion-related benzene rings [centroid-centroid distance = 3.8850 (14) Å; inter-planar distance = 3.3895 (10) Å; slippage = 1.899 Å], forming sheets lying parallel to (100).

| S-EPMC4438824 | biostudies-literature

Crystal structure of (4-hy-droxy-piperidin-1-yl)(4-methyl-phen-yl)methanone.

Project description:In the title compound, C13H17NO2, the dihedral angle between the planes of the piperidine and benzene rings is 51.7?(2)°. The bond-angle sum around the N atom [359.8?(3)°] indicates sp (2) hybridization of the atom. In the crystal, O-H?O hydrogen bonds link the mol-ecules, forming chains along [001].

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Crystal structure of [4-(chloro-meth-yl)phen-yl](4-hy-droxy-piperidin-1-yl)methanone.

Project description:The title compound, C13H16ClNO2, crystallized with two independent mol-ecules in the asymmetric unit (A and B). The piperidinol ring in mol-ecule B is disordered over two positions with a site occupancy ratio of 0.667 (5):0.333 (5). In both mol-ecules these rings have a chair conformation, including the minor component in mol-ecule B. Their mean planes are inclined to the benzene ring by 45.57 (13)° in mol-ecule A, and by 50.5 (4)° for the major component of the piperidine ring in mol-ecule B. In the crystal, the individual mol-ecules are linked by O-H⋯O hydrogen bonds, forming chains of A and B mol-ecules along the [100] direction. The chains are inter-linked by C-H⋯O hydrogen bonds, forming ribbons.

| S-EPMC4647401 | biostudies-literature

Methyl (E)-2-({2-[(E)-(hy-droxy-imino)-meth-yl]phen-oxy}meth-yl)-3-(4-methyl-phen-yl)acrylate.

Project description:In the title compound, C(19)H(19)NO(4), the dihedral angle between the mean planes through the benzene rings is 82.18?(7)°. The C=N double bond is trans-configured. The mol-ecules are linked into centrosymmetric dimers via pairs of O-H?N hydrogen bonds with the motif R(2) (2)(6). The crystal packing also features C-H?O inter-actions. The methyl group attached to one of the aromatic rings is disordered over two almost equally occupied positions [occpancy ratio = 0.51?(4):0.49?(4)].

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