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2,2-Dichloro-N-(2,3-dimethyl-phen-yl)acetamide.

ABSTRACT: The conformation of the N-H bond in the title compound, C(10)H(11)Cl(2)NO, is syn to both the 2- and 3-methyl substituents in the aromatic ring, similar to that of the 2-chloro and 3-chloro substituents in 2,2-dichloro-N-(2,3-dichloro-phen-yl)acetamide and the 2-methyl substituent in 2,2-dichloro-N-(2-methyl-phen-yl)acetamide, but in contrast to the anti conformation observed with respect to the 3-methyl substituent in 2,2-dichloro-N-(3-methyl-phen-yl)acetamide. The bond parameters in the title compound are similar to those in 2,2-dichloro-N-phenyl-acetamide and other acetanilides. The mol-ecules of the title compound are linked into chains through N-H?O and C-H?O hydrogen bonding.

SUBMITTER: Gowda BT

PROVIDER: S-EPMC2915294 | biostudies-literature | 2007 Dec

REPOSITORIES: biostudies-literature

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2,2-Dichloro-N-(2,3-dimethyl-phen-yl)acetamide.

Gowda B Thimme BT Svoboda Ingrid I Foro Sabine S Paulus Helmut H Fuess Hartmut H

Acta crystallographica. Section E, Structure reports online 20071212 Pt 1

The conformation of the N-H bond in the title compound, C(10)H(11)Cl(2)NO, is syn to both the 2- and 3-methyl substituents in the aromatic ring, similar to that of the 2-chloro and 3-chloro substituents in 2,2-dichloro-N-(2,3-dichloro-phen-yl)acetamide and the 2-methyl substituent in 2,2-dichloro-N-(2-methyl-phen-yl)acetamide, but in contrast to the anti conformation observed with respect to the 3-methyl substituent in 2,2-dichloro-N-(3-methyl-phen-yl)acetamide. The bond parameters in the title ...[more]

PMID: 21200801

Similar Datasets

2,2-Dichloro-N-(3,5-dimethyl-phen-yl)-acetamide.

Project description:The structure of the title compound, C(10)H(11)Cl(2)NO, resembles those of 2,2-dichloro-N-phenyl-acetamide, 2,2-dichloro-N-(2-methyl-phen-yl)acetamide, 2,2-dichloro-N-(3-methyl-phen-yl)-acetamide, 2,2-dichloro-N-(4-methyl-phen-yl)acetamide, N-(3,5-dimethyl-phen-yl)acetamide and other acetanilides, with similar bond parameters. The mol-ecules in the title compound are linked into infinite chains through N-H?O and C-H?O hydrogen bonding.

| S-EPMC2915270 | biostudies-literature

2,2-Dichloro-N-(3,4-dimethyl-phen-yl)acetamide.

Project description:In the title compound, C(10)H(11)Cl(2)NO, the N-H bond is syn to the 3-methyl substituent in the aromatic ring, similar to that observed in N-(3,4-dimethyl-phen-yl)acetamide and to the 3-chloro substituent in 2,2-dichloro-N-(3,4-dichloro-phen-yl)acetamide, and contrasting with the anti conformation observed for the 3-methyl substituent in 2,2,2-trichloro-N-(3,4-dimethyl-phen-yl)acetamide. On the other hand, it is anti to the C=O bond. An inter-molecular N-H?O hydrogen bond links mol-ecules into infinite chains along the b axis.

| S-EPMC2969347 | biostudies-literature

2,2-Dichloro-N-(2,5-dichloro-phen-yl)acetamide.

Project description:The conformation of the N-H bond in the title compound, C(8)H(5)Cl(4)NO, is syn to the 2-chloro substituent and anti to the 5-chloro substituent in the aromatic ring. The bond parameters are similar to those in 2,2-dichloro-N-phenyl-acetamide and other acetanilides. In the crystal structure, the mol-ecules are linked into chains through N-H?O hydrogen bonding.

| S-EPMC2915043 | biostudies-literature

N-(2,3-Dimethyl-phen-yl)acetamide.

Project description:The conformation of the N-H bond in the structure of the title compound, C(10)H(13)NO, is syn to both the 2- and 3-methyl substituents on the aromatic ring, and is anti to the C=O bond. N-H?O hydrogen bonds link the mol-ecules into supra-molecular chains.

| S-EPMC2977664 | biostudies-literature

2,2-Dichloro-N-(3-nitro-phen-yl)acetamide.

Project description:The conformation of the N-H bond in the structure of the title compound (3NPDCA), C(8)H(6)Cl(2)N(2)O(3), is anti to the meta-nitro group, similar to that in the structures of 2-chloro-N-(3-nitro-phen-yl)acetamide (3NPCA) and 2,2,2-trichloro-N-(3-nitro-phen-yl)acetamide (3NPTCA), and the meta-chloro group in 2,2-dichloro-N-(3-chloro-phen-yl)acetamide (3CPDCA). The geometric parameters of 3NPDCA are similar to those of 2,2-dichloro-N-phenyl-acetamide, 3CPDCA, 3NPCA, 3NPTCA and other acetanilides. Inter-molecular N-H?O hydrogen bonds link the mol-ecules into chains running along the b axis.

| S-EPMC2960440 | biostudies-literature

N-(2,6-Dimethyl-phen-yl)-2,2-diphenyl-acetamide.

Project description:In the title compound, C(22)H(21)NO, the dihedral angle between the phenyl rings is 82.59?(7)°. The dimethyl-benzene ring forms dihedral angles of 52.86?(4) and 49.65?(5)° with the two phenyl rings. In the crystal, mol-ecules are linked by N-H?O hydrogen bonds, forming a C(4) chain along the c axis. The crystal also features C-H?? inter-actions.

| S-EPMC3344437 | biostudies-literature

N-(2,3-Dimethyl-phen-yl)-2,2,2-trimethyl-acetamide.

Project description:The N-H bond in the title compound, C(13)H(19)NO, is anti to the C=O bond and is also anti to both the 2- and 3-methyl substituents in the aromatic ring. In the crystal, inter-molecular N-H?O hydrogen bonds link the mol-ecules into chains propagating along the c axis.

| S-EPMC2969287 | biostudies-literature

2-(2,4-Dichloro-phen-yl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide.

Project description:In the crystal structure of the title compound, C19H17Cl2N3O2, the mol-ecules form dimers of the R2(2)(10) type through N-H?O hydrogen bonding. As a result of steric repulsion, the amide group is rotated with respect to both the dichloro-phenyl and 2,3-dihydro-1H-pyrazol-4-yl rings, making dihedral angles of 80.70?(13) and 64.82?(12)°, respectively. The dihedral angle between the dichloro-phenyl and 2,3-dihydro-1H-pyrazol-4-yl rings is 48.45?(5)° while that between the 2,3-dihydro-1H-pyrazol-4-yl and phenyl rings is 56.33?(6)°.

| S-EPMC3588232 | biostudies-literature

2-(2,6-Dichloro-phen-yl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide.

Project description:In the title compound, C19H17Cl2N3O2, the amide group is planar and, through N-H?O hydrogen bonding to an adjoining mol-ecule, forms dimers of the R2(2)(10) type. As a result of steric repulsion, the amide group is rotated with respect to both the dichloro-phenyl and 2,3-dihydro-1H-pyrazol-4-yl rings, making dihedral angles of 71.63?(11) and 57.93?(10)°, respectively. The dihedral angle between the dichloro-phenyl and 2,3-dihydro-1H-pyrazol-4-yl rings is 76.60?(10)° while that between the 2,3-dihydro-1H-pyrazol-4-yl and phenyl rings is 49.29?(7)°. The crystal structure also features weak C-H?O inter-actions.

| S-EPMC3588313 | biostudies-literature

2-(3,4-Dichloro-phen-yl)-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide.

Project description:In the title compound, C19H17Cl2N3O2, there are three mol-ecules (A, B and C) in the asymmetric unit and each differs in the conformation adopted. As a result of steric repulsion, the amide group is rotated with respect to both the dichloro-phenyl and 2,3-dihydro-1H-pyrazol-4-yl rings, making dihedral angles of 44.5?(2) and 56.2?(2)°, respectively in A, 51.1?(2) and 54.1?(2)° in B, and 53.8?(2) and 54.6?(2)° in C. The dihedral angles between the dichloro-phenyl and 2,3-dihydro-1H-pyrazol-4-yl rings are 54.8?(2), 76.2?(2) and 77.5?(2)° in mol-ecules A, B and C, respectively, while the 2,3-dihydro-1H-pyrazol-4-yl and phenyl rings make dihedral angles of 45.3?(2), 51.2?(2) and 42.8?(2)°, respectively. In the crystal, two of the mol-ecules are linked through N-H?O hydrogen bonding to an adjoining mol-ecule, forming dimers of the R2(2)(10) type, while the third mol-ecule forms such dimers with itself. C-H?O inter-actions link the dimers.

| S-EPMC3588482 | biostudies-literature

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