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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

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-(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-other

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 ?-? 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 ?-? stacking inter-actions [centroid-centroid distance = 3.888?(3)?Å], forming a three-dimensional network.

| S-EPMC3998274 | biostudies-literature

N-[11-(4-Chloro-phen-yl)-11,12-dihydro-benzo[c]phenanthridin-6-yl]benzamide.

Project description:There are two independent mol-ecules in the asymmetric unit of the title compound, C(30)H(21)ClN(2)O, which differ slightly in the orientation of the unsubstituted phenyl ring. Inter-molecular C-H?? inter-actions stabilize the crystal structure. The crystal studied was found to be a racemic twin. The dihedral angles between the substituted phenyl ring and the benzo[c]phenanthridine system are 87.13?(5) and 79.25?(5)° in the two molecules.

| S-EPMC3009300 | biostudies-literature

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