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N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-di-hydro-1H-pyrazol-4-yl)-2-(4-nitro-phen-yl)acetamide.

ABSTRACT: In the title compound, C19H18N4O4, the nitro-phenyl and phenyl rings are twisted by 67.0 (6) and 37.4 (4)°, respectively, with respect to the pyrazole ring plane [maximum deviation = 0.0042 (16) Å]. The dihedral angle between the mean planes of the phenyl rings is 59.3 (3)°. The amide group, with a C-N-C-C torsion angle of 177.54 (13)°, is twisted away from the plane of the pyrazole ring in an anti-periplanar conformation. In the crystal, N-H⋯O hydrogen bonds involving the carbonyl group on the pyrazole ring and the amide group, together with weak C-H⋯O inter-actions forming R 2 (2)(10) graph-set motifs, link the mol-ecules into chains along [100]. Additional weak C-H⋯O inter-actions involving the nitro-phenyl rings further link the mol-ecules along [001], also forming R 2 (2)(10) graph-set motifs, thereby generating (010) layers.

SUBMITTER: Kaur M

PROVIDER: S-EPMC4051092 | biostudies-literature |

REPOSITORIES: biostudies-literature

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N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-di-hydro-1H-pyrazol-4-yl)-2-phenyl-acetamide.

Project description:The title compound, C19H19N3O2, crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. In mol-ecule A, the pyrazole ring adopts a slightly disordered half-chair conformation while in B it is planar [r.m.s. deviation = 0.0386?(15)?Å]. The dihedral angle between the mean planes of the two phenyl rings is 56.2?(8) in A and 38.2?(3)° in B. The N-phenyl substituent on the pyrazole ring is twisted by 46.5?(2) in A and 58.6?(4)° in B while the extended phenyl ring is twisted by 82.2?(8) in A and 87.5?(9)° in B. The mean plane of the amide group forms an angle of 74.8?(3) in A and 67.7?(1)° in B with respect to the phenyl ring. In addition, the amide group is rotated by 51.4?(1) in A and 53.6?(2)° in B from the the mean plane of the pyrazole ring. In the crystal, the two molecules are linked via N-H?O hydrogen bonds, supported by weak C-H?O inter-actions, forming dimers enclosing an R 2 (2)(10) ring motif. The dimers are linked via C-H?O inter-actions, forming a three-dimensional structure.

| S-EPMC3885014 | biostudies-literature

N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)acetamide-naphthalene-2,3-diol (1/1).

Project description:In the reaction of naphthalene-2,3-diol and 4-amino-anti-pyrine in the presence of acetic acid, the amine function is acetyl-ated and the resulting acetamide co-crystallizes with the diol in the title compound, C(13)H(15)N(3)O(2)·C(10)H(8)O(2), with 1:1 molar stoichiometry. The two components are linked by two O-H⋯O=C hydrogen bonds. One of the hy-droxy groups inter-acts with the pyrazolone carbonyl O atom and the other hy-droxy group inter-acts with the amide O atom of another component, generating a chain motif. Adjacent chains are linked into a layer motif via N-H⋯O inter-actions involving only the heterocyclic acetamide component.

| S-EPMC3007032 | 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

N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-[4-(methyl-sulfan-yl)phen-yl]acetamide.

Project description:In the title compound, C(20)H(21)N(3)O(2)S, the 2,3-dihydro-1H-pyrazole ring is nearly planar (r.m.s. deviation = 0.023 Å) and forms dihedral angles of 16.96 (6) and 38.93 (6)° with the benzene and phenyl rings, respectively. The dihedral angle between the benzene and phenyl rings is 55.54 (6)°. The mol-ecular conformation is consolidated by an intra-molecular C-H⋯O hydrogen bond, which forms an S(6) ring. In the crystal, inversion dimers linked by pairs of N-H⋯O(p) (p = pyrazole) hydrogen bonds generate R(2) (2)(10) loops. The dimers are linked by C-H⋯O hydrogen bonds into sheets lying parallel to (100).

| S-EPMC3435699 | biostudies-literature

Crystal structure of ethyl N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-di-hydro-1H-pyrazol-4-yl)carbamate.

Project description:In the title compound, C14H17N3O3, the dihedral angle between the benzene ring and the five-membered di-hydro-pyrazole ring is 52.26 (9)°. The ethyl ester group is approximately planar (r.m.s. deviation 0.0568 Å) and subtends an angle 67.73 (8)° to the pyrazole ring. In the crystal, molecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(10) ring motif. Weaker C-H⋯O contacts link these dimers into a three-dimensional network of mol-ecules stacked along the a-axis direction. Offset π-π stacking inter-actions between the benzene rings [centroid-to-centroid distance = 3.8832 (12) Å] further stabilize the crystal packing.

| S-EPMC4438802 | biostudies-literature

N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)formamide.

Project description:In the title compound, C(12)H(13)N(3)O(2), the dihedral angle between the pyrazole and benzene rings is 50.0?(3)°. In the crystal, mol-ecules are linked by inter-molecular N-H?O hydrogen bonds to form a three-dimensional network. Two weak C-H?? inter-actions reinforce the crystal packing.

| S-EPMC3120348 | biostudies-literature

4-((E)-{2-[N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)carboximido-yl]benzyl-idene}amino)-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one.

Project description:The title compound, C(30)H(28)N(6)O(2), is a symmetric diimine derived from ortho-dibenzaldehyde. Both C=N bonds are (E)-configured. The terminal N-bonded phenyl groups adopt staggered conformations relative to their respective parent heterocycles, the relevant least-squares planes inter-sect at angles of 32.35?(11) and 38.59?(10)°. In the crystal, C-H?O contacts connect the mol-ecules into chains along the b axis and give rise to a C(1) (1)(14)C(1) (1)(14) and a R(2) (2)(12) pattern on different levels of graph-set analysis. The shortest inter-centroid distance between two centroids was found at 4.2074?(11)?Å between the two five-membered heterocycles.

| S-EPMC3201528 | biostudies-literature

3-(2,3-Dimethyl-5-oxo-1-phenyl-2,5-di-hydro-1H-pyrazol-4-yl)sydnone.

Project description:IN THE TITLE SYDNONE COMPOUND [SYSTEMATIC NAME: 3-(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yl)-1,2,3-oxadiazol-3-ium-5-olate], C(13)H(12)N(4)O(3), the oxadiazole and pyrazole rings are essentially planar [maximum deviations = 0.006?(1) and 0.019?(1)?Å, respectively] and are inclined at inter-planar angles of 37.84?(4) and 46.60?(4)°, respectively, with respect to the benzene ring. In the crystal, adjacent mol-ecules are inter-connected into a three-dimensional supra-molecular network via inter-molecular C-H?O hydrogen bonds. Weak inter-molecular ?-? aromatic stacking inter-actions [centroid-centroid distance = 3.5251?(5)?Å] further stabilize the crystal packing.

| S-EPMC2979459 | biostudies-literature

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