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Crystal structure of 3-chloro-N-(2-nitro-phen-yl)benzamide.

ABSTRACT: In the title compound, C13H9ClN2O3, the mean plane of the central amide fragment (r.m.s. deviation = 0.016?Å) subtends dihedral angles of 15.2?(2) and 8.2?(2)° with the chloro- and nitro-substituted benzene rings, respectively. An intra-molecular N-H?O hydrogen bond generates an S(6) ring. In the crystal, mol-ecules are linked by weak C-H?O hydrogen bonds, forming C(7) chains which propagate along [010], but no Cl?Cl short contacts are observed.

SUBMITTER: Moreno-Fuquen R

PROVIDER: S-EPMC4555397 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature

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Crystal structure of 3-chloro-N-(2-nitro-phen-yl)benzamide.

Moreno-Fuquen Rodolfo R Azcárate Alexis A Kennedy Alan R AR

Acta crystallographica. Section E, Crystallographic communications 20150822 Pt 9

In the title compound, C13H9ClN2O3, the mean plane of the central amide fragment (r.m.s. deviation = 0.016 Å) subtends dihedral angles of 15.2 (2) and 8.2 (2)° with the chloro- and nitro-substituted benzene rings, respectively. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming C(7) chains which propagate along [010], but no Cl⋯Cl short contacts are observed. ...[more]

PMID: 26396898

Similar Datasets

Crystal structure of 2-nitro-N-(2-nitro-phen-yl)benzamide.

Project description:In the title compound, C13H9N3O5, the mean plane of the non-H atoms of the central amide fragment C-N-C(=O)-C [r.m.s. deviation = 0.0442 Å] forms dihedral angles of 71.76 (6) and 24.29 (10)° with the C-bonded and N-bonded benzene rings, respectively. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds forming C(4) chains along [100]. Weak C-H⋯O contacts link the mol-ecules into (100) sheets containing edge-fused R 4 (4)(30) rings. Together, the N-H⋯O and C-H⋯O hydrogen bonds generate a three-dimensional network.

| S-EPMC4459296 | biostudies-literature

N-(4-Chloro-phen-yl)-4-nitro-benzamide.

Project description:The title compound, C(13)H(9)ClN(2)O(3), is almost planar, showing a dihedral angle of 4.63 (6)° between the aromatic ring planes. The nitro group also lies in the plane, the C-C-N-O torsion angle being 6.7 (2)°. There is an intamolecular C-H⋯O hydrogen bond. The crystal structure features N-H⋯O(nitro) hydrogen bonds that link the mol-ecules into zigzag chains extending along [010].

| S-EPMC3435803 | biostudies-literature

N-(2-Chloro-4-nitro-phen-yl)-2-nitro-benzamide.

Project description:In the title compound, C(13)H(8)ClN(3)O(5), the dihedral angle between the two aromatic rings is 70.74 (6)°. The nitro groups of the Cl-substituted and benzamide benzene rings are twisted by 2.6 (1) and 31.3 (2)°, respectively. The crystal packing shows inter-molecular C-H⋯O hydrogen bonds that link mol-ecules into sheets stacked along [010].

| S-EPMC2961029 | biostudies-literature

N-[(2-Chloro-phen-yl)sulfon-yl]-3-nitro-benzamide.

Project description:In the title compound, C13H9ClN2O5S, the dihedral angle between the benzene rings is 74.86 (11)°. The mol-ecule is twisted at the S atom, with a dihedral angle of 82.53 (13)° between the sulfonyl benzene ring and the S-N-C=O segment. In the crystal, mol-ecules are linked into inversion dimers through pairs of N-H⋯O hydrogen bonds, thereby forming R 2 (2)(8) loops. Mol-ecules are linked into C(7) [010] chains by weak C-H⋯O hydrogen bonds, and C-H⋯π inter-actions are also observed.

| S-EPMC3770368 | biostudies-literature

Crystal structure of 2,3-dimeth-oxy-N-(4-nitro-phen-yl)benzamide.

Project description:In the title compound, C15H14N2O5, the benzene rings are nearly coplanar, making a dihedral angle of 4.89 (8)°. An intra-molecular N-H⋯O hydrogen bond occurs between the imino and meth-oxy groups. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into supra-molecular chains propagating along the a-axis direction. π-π stacking is observed between parallel benzene rings of neighbouring chains, the centroid-to-centroid distance being 3.6491 (10) Å. Three-dimensional Hirshfeld surface analyses and two-dimensional fingerprint plots have been used to analyse the inter-molecular inter-actions present in the crystal.

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4-Nitro-N-(3-nitro-phen-yl)benzamide.

Project description:The title compound, C(13)H(9)N(3)O(5), prepared as a solid derivative of 3-nitro-analine via reaction with 4-nitro-benzoyl chloride, crystallizes in a chiral space group. The mol-ecule is non-planar with a dihedral angle of 26.1?(1)° between the two benzene rings. Both nitro groups are twisted slightly out of the plane of their corresponding benzene rings, making dihedral angles of 10.7?(4) and 13.5?(4)°. The mol-ecules are stacked along the a axis with benzene ring centroid-centroid distances of 3.8878?(6)?Å. In the crystal, inter-molecular benzene C-H?O inter-actions involving one nitro group and the carbonyl group link the mol-ecules, forming chains along [001]. An additional set of aromatic C-H?O inter-actions with the second nitro group form chains along [101], connecting adjacent chains to create layers perpendicular to the b axis.

| S-EPMC3201324 | biostudies-literature

N-(2-Nitro-phen-yl)benzamide.

Project description:In the title compound, C(13)H(10)N(2)O(3), the central C-C(=O)-N-C amide unit makes dihedral angles of 21.68?(4) and 19.08?(4)°, respectively, with the phenyl and nitro-benzene rings. The two aromatic rings are inclined at 3.74?(3)° and the nitro group is skewed out of the attached benzene ring plane by 18.55?(8)°. An intra-molecular N-H?O inter-action to an O atom of the nitro substituent generates an S(6) ring motif. In the crystal, C-H?O contacts generate two centrosymmetric ring systems with R(2) (2)(14) and R(2) (2)(20) graph-set motifs, forming zigzag chains down the a axis. ?-? inter-actions between adjacent phenyl and nitro-benzene rings [centroid-centroid distance = 3.6849?(6)?Å] also form centrosymmetric dimers. These and an additional C-H?O hydrogen bond generate an extensive three-dimensional network structure.

| S-EPMC2977104 | biostudies-literature

Crystal structures of isomeric 4-bromo-<i>N</i>-[(2-nitro-phen-yl)sulfon-yl]benzamide and 4-bromo-<i>N</i>-[(4-nitro-phen-yl)sulfon-yl]benzamide.

Project description:The syntheses and crystal structures of the isomeric 4-bromo-N-[(2-nitro-phen-yl)sulfon-yl]benzamide, (I), and 4-bromo-N-[(4-nitro-phen-yl)sulfon-yl]benzamide, (II), are described (mol-ecular formula = C13H9BrN2O5S in each case). The asymmetric unit of (I) contains two independent mol-ecules [(IA) and (IB)], while that of (II) contains one mol-ecule. The benzoic acid aromatic ring of mol-ecule (IA) is disordered due to rotation about the Car-C(=O) bond over two orientations in a 0.525 (9):0.475 (9) ratio. The dihedral angle between the benzene rings is 85.9 (3)° in (IA) and 65.22 (19)° in (IB), while in (II), the corresponding value is 56.7 (7)°. In the crystals of (I) and (II), N-H⋯O, C-H⋯O and C-H⋯π inter-actions generate three-dimensional networks.

| S-EPMC5347043 | biostudies-literature

Crystal structure of N-{4-[(6-chloro-pyridin-3-yl)meth-oxy]phen-yl}-2,6-di-fluoro-benzamide.

Project description:In the title compound, C19H13ClF2N2O2, the conformation of the N-H bond in the amide segment is anti to the C=O bond. The mol-ecule is not planar, with dihedral angles between the central benzene ring and the outer benzene and pyridyl rings of 73.35?(7) and 81.26?(6)°, respectively. A weak intra-molecular C-H?O hydrogen bond occurs. In the crystal, N-H?N, C-H?O and C-H?F hydrogen bonds lead to the formation of dimers. The N-H?N inversion dimers are linked by ?-? contacts between adjacent pyridine rings [centroid-centroid = 3.8541?(12)?Å] and C-H?? inter-actions. These contacts combine to stack the mol-ecules along the a axis.

| S-EPMC4704742 | biostudies-literature

N-(3-Chloro-phen-yl)benzamide.

Project description:The conformation of the N-H bond in the structure of the title compound (N3CPBA), C(13)H(10)ClNO, is anti to the meta chloro substituent in the aniline benzene ring, similar to that observed with respect to the ortho chloro substituent in N-(2-chloro-phen-yl)benzamide (N2CPBA) and meta chloro substituent in N-(3,4-dichloro-phen-yl)benzamide (N34DCPBA), but in contrast to the syn conformation observed with respect to both the ortho and the meta chloro substituents in N-(2,3-dichloro-phen-yl)benzamide (N23DCPBA). The bond parameters in N3CPBA are similar to those in N-phenyl-benzamide, N2CPBA, N23DCPBA, N34DCPBA and other benzanilides. The amide group -NHCO- makes a dihedral angle of 18.2 (2)° with the benzoyl ring, while the dihedral angle between the two benzene rings is 61.0 (1)°. The mol-ecules are linked into chains along the b axis by N-H⋯O hydrogen bonds.

| S-EPMC2960316 | biostudies-literature

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