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(E)-2-[(2-Ethyl-phen-yl)iminiometh-yl]-6-hydroxy-phenolate.

ABSTRACT: The mol-ecule of the title compound, C(15)H(15)NO(2), crystallizes in a zwitterionic form, and displays an E configuration about the C=N bond. The dihedral angle between the two aromatic rings is 5.59?(6)°. An intra-molecular N-H?O hydrogen bond generates an S(6) ring motif. In the crystal structure, pairs of mol-ecules are linked into centrosymmetric R(2) (2)(10) dimers by pairs of O-H?O hydrogen bonds. Aromatic ?-? inter-actions are observed between the benzene rings of adjacent dimers [centroid-centroid distance = 3.4808?(7)?Å].

SUBMITTER: Yaz?c? S

PROVIDER: S-EPMC2979895 | biostudies-other | 2010

REPOSITORIES: biostudies-other

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(E)-2-[(2-Ethyl-phen-yl)iminiometh-yl]-6-hydroxy-phenolate.

Yazıcı Serap S Albayrak Ciğdem C Gümrükçüoğlu Ismail I Senel Ismet I Büyükgüngör Orhan O

Acta crystallographica. Section E, Structure reports online 20100127 Pt 2

The mol-ecule of the title compound, C(15)H(15)NO(2), crystallizes in a zwitterionic form, and displays an E configuration about the C=N bond. The dihedral angle between the two aromatic rings is 5.59 (6)°. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal structure, pairs of mol-ecules are linked into centrosymmetric R(2) (2)(10) dimers by pairs of O-H⋯O hydrogen bonds. Aromatic π-π inter-actions are observed between the benzene rings of adjacent dimers [centro ...[more]

PMID: 21579864

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(E)-2-[(2-Hydroxy-ethyl)iminiometh-yl]-6-methoxy-phenolate.

Project description:The title Schiff base compound, C(10)H(13)NO(3), obtained by the reaction of 2-hydr-oxy-3-methoxy-benzaldehyde and 2-amino-ethanol in methanol solution, crystallizes in a zwitterionic form, in which the mol-ecule adopts a trans configuration about the central C=N bond. An intra-molecular N-H?O hydrogen bond occurs. In the crystal structure, mol-ecules are linked into chains by inter-molecular O-H?O hydrogen bonding.

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(E)-4-Bromo-2-[(2-hydroxy-phen-yl)iminiometh-yl]phenolate.

Project description:The title compound, C(13)H(10)BrNO(2), crystallizes in a zwitterionic form. The zwitterion exists in a trans configuration about the C=N bond and is almost planar, the dihedral angle between the two benzene rings being 2.29?(9)°. An intra-molecular N-H?O hydrogen bond formed between the iminium NH(+) and the phenolate O(-) atoms generates an S(6) ring motif. In the crystal, the zwitterions are linked through O-H?O hydrogen bonds into chains along [101] and these chains are further connected through C-H?Br inter-actions into a two-dimensional network perpendicular to (101). C?C [3.572?(3)-3.592?(3)?Å] and C?Br [3.5633?(19)-3.7339?(18)?Å] short contacts are observed. The crystal studied was a twin with twin law 00, 00, 001 with a domain ratio of 0.09919?(2):0.90081?(2).

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(E)-4-Allyl-2-[(2-hydroxy-phen-yl)iminiometh-yl]-6-methoxy-phenolate.

Project description:The title compound, C(17)H(17)NO(3), crystallizes in a zwitterionic form with cationic iminium and anionic enolate groups. The zwitterion exists in a trans configuration about the C=N bond. The dihedral angle between the two benzene rings is 13.42 (7)°. The meth-oxy group is almost coplanar [C-O-C-C = 2.1 (2)°] with the attached ring whereas the allyl unit is oriented at a dihedral angle of 67.9 (1)°. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, the mol-ecules are linked into zigzag chains along [010] by O-H⋯O hydrogen bonds. In addition, weak C-H⋯π inter-actions are observed.

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Project description:The asymmetric unit of the title compound, C(20)H(16)N(2)O(4)·CH(3)OH, contains two Schiff base zwitterions and two methanol solvent mol-ecules. The dihedral angles between the central benzene ring and the two outer benzene rings of the Schiff base are 2.57?(7) and 52.30?(7)° in one mol-ecule and 5.83?(7) and 49.82?(7)° in the other mol-ecule. Intra-molecular O-H?N and N-H?O hydrogen bonds generate S(6) ring motifs, whereas intra-molecular N-H?N hydrogen bonds generate S(5) ring motifs. In the crystal structure, O-H?O, hydrogen bonds and weak C-H?O inter-actions link the mol-ecules into one-dimensional chains along the b-axis direction and are further connected by O-H?O and weak C-H?O inter-actions into a three-dimensional network. C-H?? and ?-? inter-actions [centroid-centroid distances = 3.6228?(9) and 3.6881?(9)?Å] are also observed in the crystal structure.

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2-((E)-{2-[(E)-2,3-Dihydroxy-benzyl-ideneamino]-5-methyl-phen-yl}iminiometh-yl)-6-hydroxy-phenolate.

Project description:The asymmetric unit of the title Schiff base compound, C(21)H(18)N(2)O(4), consists of four independent zwitterions (A, B, C and D) with similar conformations. In each independent mol-ecule, the methyl group is disordered over two positions; the occupancies of the two positions are 0.819?(5) and 0.181?(5) in mol-ecule A, 0.912?(5) and 0.088?(5) in B, 0.734?(5) and 0.266?(5) in C, and 0.940?(6) and 0.060?(6) in D. The dihydroxy-phenyl and the hydroxy-phenolate rings in mol-ecule A form dihedral angles of 17.36?(12) and 13.30?(12)°, respectively, with the central benzene ring, whereas the respective angles for mol-ecules B, C and D are 30.22?(11)/7.46?(11), 35.26?(12)/11.01?(12) and 39.89?(12)/4.29?(12)°. In all independent mol-ecules, intra-molecular N-H?O and O-H?N hydrogen bonds generate S(6) ring motifs. The four independent mol-ecules are linked into two pairs, viz. A-B and C-D, by inter-molecular O-H?O hydrogen bonds. These pairs are linked into a two-dimensional network parallel to the ab plane by C-H?O hydrogen bonds. In addition, C-H?? and ?-? [centroid-centroid distance = 3.5153?(14)-3.7810?(15)?Å] inter-actions stabilize the crystal structure.

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2-{1-[2-(Bis{2-[1-(5-chloro-2-hydroxy-phen-yl)ethyl-ideneamino]eth-yl}amino)-ethyl-iminio]eth-yl}-4-chloro-phenolate toluene hemisolvate.

Project description:In the toluene hemisolvated tripodal tris-(2-amino-ethyl)amine Schiff base, C(30)H(33)Cl(3)N(4)O(3)·0.5C(7)H(8), one of the three imino N atoms is protonated, forming a hydrogen bond with the O atom at an adjacent benzene ring. The other two imino N atoms act as hydrogen-bond acceptors from phenolate OH groups. The toluene solvent mol-ecule is disordered about a centre of inversion.

| S-EPMC2968323 | biostudies-literature

Low-temperature redetermination of 4-chloro-2-[tris-(hydroxy-meth-yl)methyl-imino-meth-yl]phenol as zwitterionic 4-chloro-2-[tris-(hydroxy-meth-yl)methyl-iminiometh-yl]phenolate.

Project description:The title Schiff base, C(11)H(14)ClNO(4), originally refined as a neutral mol-ecule [Chumakov, Antosyak, Mazus, Tsapkov & Samus (2000), Crystallogr. Rep.45, 945-950], is inter-preted as a zwitterionic compound. There are two independent zwitterions in the asymmetric unit. Five of the six hydr-oxy groups of the -CH(2)OH fragments are disordered. In one zwitterion, two are disordered over three sites [0.53?(1):0.33?(1):0.14?(1) and 0.65?(1):0.18?(1):0.17?(1)] and the third over two sites [0.66?(1):0.34?(1)]. In the second zwitterion, two are disordered over two sites [0.84?(1):0.16?(1) and 0.83?(1):0.17?(1)] and the third hydr-oxy group is ordered.

| S-EPMC2960041 | biostudies-literature

Tris{2-meth-oxy-6-[(4-methyl-phen-yl)iminiometh-yl]phenolate-?O,O'}tris-(thio-cyanato-?N)europium(III).

Project description:The metal center in the structure of the title compound, [Eu(NCS)(3)(C(15)H(15)NO(2))(3)], is coordinated by three Schiff base 2-meth-oxy-6-[(4-methyl-phen-yl)iminiometh-yl]phenolate (L) ligands and three independent thio-cyanate ions. In the crystal structure, the acidic H atom is located on the Schiff base N atom and hydrogen bonded to the phenolate O atom. The coordination environment of the Eu(III) ion is nine-coordinate by three chelating methoxy-phenolate pairs of O atoms and three N-atom terminals of the thio-cyanate ions. The compound is isostructural with the Ce(III) analogue [Liu et al. (2009 ?). Acta Cryst. E65, m650].

| S-EPMC2972108 | biostudies-literature

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