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N-(3-Bromo-1,4-dioxo-1,4-dihydro-2-naphth-yl)-2-chloro-N-(2-chloro-benzoyl)benzamide.

ABSTRACT: The title compound, C(24)H(12)BrCl(2)NO(4), was synthesized from 2-amino-3-bromo-1,4-naphthoquinone and 2-chloro-benzoyl chloride. The crystal structure shows that each of the chloro-phenyl rings is inclined at about 60° to the naphthoquinone ring system. The two chloro-phenyl rings adopt a conformation that ensures that chlorine substituents are anti so as to reduce electronic repulsion. An examination of the packing shows close O⋯Br and Cl⋯Cl contacts of 2.947 (2) and 3.346 (1) Å, respectively. In addition, the molecules are linked by weak intermolecular C-H⋯O and C-H⋯Cl interactions.

SUBMITTER: Akinboye ES

PROVIDER: S-EPMC2967943 | biostudies-literature |

REPOSITORIES: biostudies-literature

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N-(3-Bromo-1,4-dioxo-1,4-dihydro-2-naphth-yl)-4-fluoro-N-(4-fluoro-benzo-yl)benzamide.

Project description:In the title compound, C(24)H(12)BrF(2)NO(4), synthesized from 2-amino-3-bromo-1,4-naphthoquinone and 4-fluoro-benzoyl chloride, the two p-fluoro-phenyl rings are inclined at 73.9?(1) and 73.6?(1)° to the naphthoquinone ring system. The two imido carbonyl O atoms are anti to each other, while the fluoro-phenyl rings are located opposite each other, connected to the imide group in a funnel-like arrangement. This conformation allows the fluorine groups be oriented slightly away from each other. An examination of the packing shows a close inter-molecular F?O contact of 2.982?(5)?Å and a Br?O contact of 2.977?(4)?Å. In addition, the mol-ecules are linked by weak inter-molecular C-H?O and C-H?F inter-actions.

| S-EPMC2968378 | biostudies-literature

N-(1,4-Dioxo-1,4-dihydro-naphthalen-2-yl)benzamide.

Project description:The title compound, C(17)H(11)NO(3), was an inter-mediate synthesized during bis-acyl-ation of 2-amino-1,4-naphtho-quinone with benzoyl chloride. A mixture of block- and needle-shaped crystals were obtained after column chromatography. The block-shaped crystals were identified as the imide and the needles were the title amide. The naphtho-quinone scaffold is roughly planar (r.m.s. deviation = 0.047 Å for the C atoms). The N-H and C=O bonds of the amide group are anti to each other. A dihedral angle between the naphtho-quinone ring system and the amide group of 3.56 (3)°, accompanied by a dihedral angle between the amide group and the phenyl group of 9.51 (3)°, makes the naphtho-quinone ring essentially coplanar with the phenyl ring [dihedral angle = 7.12 (1)°]. In the crystal, molecules are linked by a weak N-H⋯O hydrogen bond and by two weak C-H⋯O interactions leading to the formation of zigzag chains along [010].

| S-EPMC3435808 | biostudies-literature

4-(8-Hydr-oxy-3-methyl-1,4-dioxo-1,4-dihydro-2-naphth-yl)butanoic acid.

Project description:In the title compound, C(15)H(14)O(5), an intramolecular O-H?O hydrogen bond occurs. In the crystal, the molecules form inversion dimers linked by pairs of O-H?O bonds, which are further linked by C-H?O interactions.

| S-EPMC2971191 | biostudies-literature

N-Benzoyl-N-(1,4-dioxonaphthalen-2-yl)benzamide.

Project description:The title mol-ecule, C(24)H(15)NO(4), crystallizes with two mol-ecules in the asymmetric unit (Z' = 2). For both mol-ecules, the two amide groups are not coplanar, as the dihedral angles of the respective NCO groups are similar at 50.37?(14) and 51.22?(13)°. However, the orientations of the substituent phenyl rings with the central naphthalene system are significantly different for the two mol-ecules; for one mol-ecule, these dihedral angles are 80.29?(3) and 80.95?(4)°, while for the second mol-ecule they are 86.63?(3) and 72.82?(4)°. The crystal packing shows the mol-ecules to be linked by weak C-H?O inter-actions.

| S-EPMC3414307 | biostudies-literature

3-Methyl-1,4-dioxo-1,4-dihydro-naphthalen-2-yl 4-amino-benzoate.

Project description:The crystal structure of the title compound, C(18)H(13)NO(4), the oxidized form of the drug aminaftone used in venous disease therapy, is characterized by the presence of ribbons of hydrogen-bonded mol-ecules parallel to the [111] crystallographic direction and by stacking inter-actions between rings [centroid-centroid distance between quinone rings = 3.684 (3) Å and between amino-benzoate rings = 4.157 (3) Å] along the ribbons.

| S-EPMC2961024 | biostudies-literature

tert-Butyl N-{3-[(3-chloro-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)amino]-prop-yl}carbamate.

Project description:In the title compound, C(18)H(21)ClN(2)O(4), the mol-ecular sytructure is stabilized by two intra-molecular N-H?O hydrogen bonds. In the crystal, mol-ecules are linked by pairs of C-H?O hydrogen bonds, forming inversion dimers with graph-set motif R(2) (2)(10). N-H?O hydrogen bonds further link the dimers into C(10) chains along [010].

| S-EPMC3414294 | biostudies-other

(8-Bromo-2,7-dimeth-oxy-1-naphth-yl)(4-chloro-phenyl)methanone.

Project description:In the title compound, C(19)H(14)BrClO(3), the naphthalene ring system and the benzene ring make a dihedral angle of 77.36 (10)°. The conformation around the central C=O group is such that the C=O bond vector forms a larger angle to the plane of the naphthalene ring system than to the plane of the benzene ring, viz. 75.73 (15)° versus 2.33 (17)°. In the crystal structure, a π-π inter-action is formed between naphthalene ring systems, with a centroid-centroid distance of 3.8363 (14) Å and a lateral offset of 1.606 Å. Inter-molecular C-H⋯Br and C-H⋯O hydrogen bonds and a C-H⋯π contact are present in the crystal structure.

| S-EPMC2983951 | biostudies-literature

(Z)-4-Chloro-N-(1-{2-[3-(4-chloro-benzoyl)ureido]eth-yl}imidazolidin-2-yl-idene)benzamide.

Project description:The title compound, C(20)H(19)Cl(2)N(5)O(2)S, was obtained from the reaction of 4-chloro-benzoyl isothio-cyanate with diethyl-ene-triamine. The imidazolidine ring is slightly twisted with an N-C-C-N torsion angle of 15.4 (4)°, while the thio-urea moiety maintains its trans-cis geometry. The mol-ecule is stabilized by intramolecular N-H⋯O hydrogen bonds. The crystal structure features N-H⋯O, N-H⋯S and C-H⋯O hydrogen bonds and π-π interactions between benzene rings with a centroid-centroid distance of 3.607 (3) Å.

| S-EPMC3394018 | biostudies-literature

N-(3-Chloro-1,4-dioxo-1,4-di-hydro-naph-thalen-2-yl)-N-propionylpropionamide.

Project description:In the title mol-ecule, C16H14ClNO4, the four essentially planar atoms of the imide group [r.m.s. deviation = 0.0286 (11) Å] form a dihedral angle of 77.36 (13)° with the naphtho-quinone group [maximun deviation = 0.111 (2) Å for the carbonyl O atom in the naphthalene 1-position] and the two imide carbonyl groups are oriented anti with respect to each other. In the crystal, mol-ecules are connected by weak C-H⋯O hydrogen bonds, as well as π-π stacking inter-actions [centroid-centroid distance = 3.888 (3) Å], forming a three-dimensional network.

| S-EPMC3998274 | biostudies-literature

N-[(2Z,4Z)-4-Benzyl-idene-6-chloro-1,4-dihydro-pyrido[2,3-d][1,3]thia-zin-2-yl-idene]benzamide.

Project description:In the crystal structure of the title compound, C(21)H(14)ClN(3)OS, mol-ecules assemble into inversion dimers via pairs of N-H⋯N hydrogen bonds involving the N-H hydrogen of the thia-zine ring and the N atom of the pyridine ring. There is a close intra-molecular contact [2.570 (2) Å] between the carbonyl O atom of the benzamide and the S atom of the puckered thia-zine ring. The title compound can exist in two tautomeric forms, viz. amino or imino. The observed structure is compatible with the imino form on the basis of observed residual electron density and the two C-N bond lengths of 1.308 (2) and 1.353 (2) Å.

| S-EPMC3414281 | biostudies-literature

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