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Crystal structure of (4Z)-4-[(2E)-1-hydroxy-3-(naphthalen-2-yl)prop-2-en-1-yl-idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

ABSTRACT: In the title compound, C23H18N2O2, the pyrazole ring subtends dihedral angles of 2.01?(13) and 1.55?(10)° with the pendant benzene ring and the naphthalene ring system, respectively. The mol-ecule is almost planar (r.m.s. deviation for the 27 non-H atoms = 0.025?Å) and intra-molecular O-H?O and C-H?O hydrogen bonds both close S(6) loops. In the crystal, very weak aromatic ?-? stacking inter-actions between the benzene and the pyrazole rings, with centroid-centroid distances of 3.8913?(14) and 3.9285?(15)?Å, are observed.

SUBMITTER: Salim M

PROVIDER: S-EPMC4459333 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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Crystal structure of (4Z)-4-[(2E)-3-(2-chloro-phen-yl)-1-hy-droxy-prop-2-en-1-yl-idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

Project description:In the title compound, C19H15ClN2O2, the pyrazole ring is almost planar (r.m.s. deviation = 0.002 Å) and subtends dihedral angles of 5.31 (16) and 1.86 (16)° with the phenyl and chloro-benzene rings, respectively. An intra-molecular O-H⋯O hydrogen bond closes an S(6) ring and a short C-H⋯O contact is also observed. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions to generate (001) sheets. Weak aromatic π-π inter-actions between the chloro-benzene and pyrazole rings, with a centroid-centroid distance of 3.7956 (17) Å are also observed.

| S-EPMC4459312 | biostudies-literature

Crystal structure of (4Z)-4-[(2E)-3-(4-chloro-phen-yl)-1-hy-droxy-prop-2-en-1-yl-idene]-5-methyl-2-phenyl-1H-pyrazol-5(4H)-one.

Project description:In the the asymmetric unit of the title compound, C19H15ClN2O2, there are two symmetry-independent mol-ecules, which adopt similar conformations. The largest difference is observed in the dihedral angles between the phenyl and the pyrazole fragments [17.00 (12) and 23.42 (10)°]. A strong intra-molecular O-H⋯O hydrogen bond with the S (6) motif is observed in both mol-ecules. Pairs of π-π stacking inter-actions between the phenyl groups [centroid-centroid distances = 3.6627 (13) and 3.7156 (14) Å] assemble the mol-ecules into two types of centrosymmetric dimers. Weak C-H⋯O inter-actions connect mol-ecules into chains along the b axis.

| S-EPMC4459345 | biostudies-literature

(4Z)-4-[(2E)-1-Hydr-oxy-3-(4-methoxy-phen-yl)prop-2-en-ylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

Project description:The title compound, C(20)H(18)N(2)O(4), is a chalcone derivative of pyrazole. The pyrazole ring is inclined at a dihedral angle of 19.29 (12)° to the methoxy-phenyl ring mean plane, and by 1.19 (13)° to the phenyl ring. The mol-ecular structure is stabilized by an intra-molecular O-H⋯O hydrogen bond, making an almost planar (r.m.s. deviation = 0.0243 Å) six membered ring.

| S-EPMC2972098 | biostudies-literature

(4Z)-4-[(2E)-1-Hy-droxy-3-(3-nitro-phen-yl)prop-2-en-1-yl-idene]-3-methyl-1-(4-methyl-phen-yl)-1H-pyrazol-5(4H)-one.

Project description:In the title compound, C(20)H(17)N(3)O(4), the dihedral angles between the heterocyclic ring and the toluene and nitro-benzene rings are 4.21?(15) and 11.43?(14)°, respectively. The whole mol-ecule is close to planar (r.m.s. deviation for the 27 non-H atoms = 0.171?Å). Two S(6) rings are formed due to intra-molecular C-H?O and O-H?O hydrogen bonds. In the crystal, inversion dimers linked by pairs of C-H?O bonds generate R(2) (2)(10) loops and further C-H?O bonds link the dimers along the b-axis direction. There exist ?-? inter-actions between the heterocyclic rings at a centroid-centroid distance of 3.7126?(10)?Å and between the centroids of the benzene rings at a distance of 3.8710?(16)?Å.

| S-EPMC3393312 | biostudies-other

(2E)-N-Methyl-2-[(2E)-3-phenyl-prop-2-en-1-yl-idene]hydrazinecarbothio-amide.

Project description:The title compound, C(11)H(13)N(3)S, is close to being planar, with a dihedral angle of 9.64?(3)° between the benzene ring and the thio-semicarbazone mean plane, maintained by the presence of ?-conjugation in the chain linking the the two systems. In the crystal, N-H?S hydrogen bonds form centrosymmetric dimers through a cyclic association [graph-set R(2) (2)(8)].

| S-EPMC3470202 | biostudies-literature

(E)-1-(Naphthalen-1-yl)-3-(1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-one.

Project description:In the title mol-ecule, C(22)H(16)N(2)O, the phenyl ring is twisted slightly with respect to the plane of the central pyrazole ring [dihedral angle = 14.8?(2)°]; the central ring is connected to the naphthyl ring through a -CH=CH-C(=O)- fragment, whose C=C double bond has an E configuration. The pyrazole ring and naphthalene ring system are twisted by 46.3?(1)°. Weak inter-molecular C-H?O hydrogen bonds link the mol-ecules, forming supra-molecular chains running along the a axis. The crystal studied was a non-merohedral twin with a component ratio of 0.544?(2):0.456?(2).

| S-EPMC3201529 | biostudies-literature

4-Nitro-N'-[(1E,2E)-3-phenyl-prop-2-en-1-yl-idene]benzohydrazide.

Project description:In the title mol-ecule, C(16)H(13)N(3)O(3), the benzene and phenyl rings are linked through a propenyl-idene hydrazide fragment, C-C(=O)-N(H)-N=C(H)-C(H)=C(H)-, which is fully extended with torsion angles in the range 175.4?(2)-179.9?(2)°. The dihedral angle between the the benzene and phenyl rings is 58.28?(7)°. In the crystal structure, inter-molecular N-H?O hydrogen bonds link the mol-ecules into chains along the b axis and additional stabilization is provided by weak inter-molecular C-H?O hydrogen bonds.

| S-EPMC2979035 | biostudies-literature

(2E)-3-(6-Meth-oxy-naphthalen-2-yl)-1-[4-(methyl-sulfan-yl)phen-yl]prop-2-en-1-one.

Project description:The asymmetric unit of the title compound, C(21)H(18)O(2)S, consists of two crystallographically independent mol-ecules (A and B). The mol-ecules exist in a trans conformation with respect to the central C=C bond. The naphthalene ring system makes dihedral angles of 51.62 (12) (mol-ecule A) and 52.69 (12)° (mol-ecule B) with the benzene ring. In mol-ecule A, the prop-2-en-1-one group forms dihedral angles of 22.84 (15) and 29.02 (12)° with the adjacent naphthalene ring system and benzene ring, respectively, whereas the corresponding angles are 30.04 (12) and 23.33 (12)° in mol-ecule B. In the crystal, mol-ecules are linked by inter-molecular C-H⋯O hydrogen bonds into head-to-tail chains along the a axis. The crystal packing also features C-H⋯π inter-actions. The crystal studied was a pseudo-merohedral twin with twin law (100 0-10 00-1) and a refined component ratio of 0.6103 (16):0.3897 (16).

| S-EPMC3394057 | biostudies-literature

(4Z)-4-[(2-Chloro-anilino)(phen-yl)methyl-idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

Project description:The title compound, C(23)H(18)ClN(3)O, exists in an enamine-keto form with the amino group involved in an intra-molecular N-H?O hydrogen bond. The five-membered ring is nearly planar, the largest deviation being 0.0004?(7)?Å, and makes dihedral angles of 16.62?(6), 41.89?(5) and 71.27?(4)° with the phenyl rings. In the crystal, weak C-H?O hydrogen bonds link the mol-ecules into supra-molecular chains along the b axis.

| S-EPMC3379412 | biostudies-literature

(4Z)-4-[(2,6-Diisopropyl-anilino)(phen-yl)methyl-idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

Project description:In the title compound, C(29)H(31)N(3)O, the three terminal benzene rings are oriented at dihedral angles of 20.7 (3), 65.8 (3) and 72.6 (3)° with respect to the central pyrazolone ring. Intra-molecular N-H⋯O hydrogen bonding occurs between the imine and carbonyl groups. Inter-molecular C-H⋯π inter-actions are present in the crystal structure.

| S-EPMC3051710 | biostudies-literature

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