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4-{(4Z)-4-[(2Z)-3-(4-Fluoro-anilino)-1-hy-droxy-but-2-en-1-yl-idene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl}-benzene-sulfonamide.

ABSTRACT: In the title compound, C(20)H(19)FN(4)O(4)S, the pyrazole and benzene-sulfonamide rings are coplanar [dihedral angle = 5.02?(15)°] but this planarity does not extend over the entire mol-ecule, the dihedral angle between the terminal six-membered rings being 33.24?(14)°. Intra-molecular hy-droxy-hy-droxy O-H?O and amine-hy-droxy N-H?O hydrogen bonds, as a well as a tight C-H?O(carbon-yl) inter-action, lead to a sequence of three fused S(6) rings. Supra-molecular chains along the a axis feature in the crystal packing; these chains are stabilized by amine-sulfonamide N-H?O and amine-pyrazole N-H?N hydrogen bonds.

SUBMITTER: Asiri AM

PROVIDER: S-EPMC3295527 | biostudies-other | 2012 Mar

REPOSITORIES: biostudies-other

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4-{(4Z)-4-[(2Z)-3-(4-Fluoro-anilino)-1-hy-droxy-but-2-en-1-yl-idene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl}-benzene-sulfonamide.

Asiri Abdullah M AM Faidallah Hassan M HM Ng Seik Weng SW Tiekink Edward R T ER

Acta crystallographica. Section E, Structure reports online 20120217 Pt 3

In the title compound, C(20)H(19)FN(4)O(4)S, the pyrazole and benzene-sulfonamide rings are coplanar [dihedral angle = 5.02 (15)°] but this planarity does not extend over the entire mol-ecule, the dihedral angle between the terminal six-membered rings being 33.24 (14)°. Intra-molecular hy-droxy-hy-droxy O-H⋯O and amine-hy-droxy N-H⋯O hydrogen bonds, as a well as a tight C-H⋯O(carbon-yl) inter-action, lead to a sequence of three fused S(6) rings. Supra-molecular chains along the a axis feature in ...[more]

PMID: 22412638

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(2Z)-3-(4-Fluoro-anilino)-1-(5-hy-droxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)but-2-en-1-one.

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Project description:With respect to the aliphatic planar five-membered ring (r.m.s. deviation = 0.011?Å) of the title compound, C(15)H(13)N(3)O(2)S, the phenyl ring is aligned at 6.9?(1)° and the phenyl-ene ring at 2.4?(1)°, so that the three rings are nearly coplanar. The amino group has the N atom in a pyramidal geometry; the group is a hydrogen-bond donor to the sulfonyl O atom of one mol-ecule and to the ketonic O atom of another mol-ecule, resulting in the formation of a layer parallel to the bc plane.

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1-[3,5-Bis(4-fluoro-phen-yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone.

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1-[3-(4-Fluoro-phen-yl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone.

Project description:In the title compound, C(17)H(15)FN(2)O, the pyrazoline ring adopts a flattened envelope conformation. The dihedral angle between the fluoro-substituted benzene ring and the phenyl ring is 69.20 (5)°. In the crystal, a pair of C-H⋯O hydrogen bonds link neighbouring mol-ecules, forming an inversion dimer. The crystal structure is further consolidated by C-H⋯π inter-actions and by a π-π inter-action with a centroid-centroid distance of 3.7379 (6) Å.

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(2Z)-1-(5-Hy-droxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-3-(4-methyl-anilino)-but-2-en-1-one.

Project description:A twist is evident in the title compound, C(21)H(21)N(3)O(2), the dihedral angle between the terminal six-membered rings being 29.46?(10)°; the linked five- and six-membered rings are coplanar [1.30?(11)°]. The carbonyl O atom accepts intra-molecular hydrogen bonds from the adjacent hy-droxy and amine groups. The three-dimensional crystal packing is achieved through C-H?? inter-actions.

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(2Z)-3-(3-Bromo-anilino)-1-(5-hy-droxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)but-2-en-1-one.

Project description:In the title compound, C(20)H(18)BrN(3)O(2), the central carbonyl group forms amine-N-H?O and hy-droxy-O-H?O hydrogen bonds, which lead to two fused S(6) rings. The N-bound phenyl ring is coplanar with the five-membered ring to which it is attached [dihedral angle = 5.22?(18)°], but the dihedral angle [33.87?(17)°] between the terminal phenyl and bromo-benzene rings indicates an overall twist in the mol-ecule. In the crystal packing, mol-ecules assemble into dimeric aggregates via C-H?? inter-actions.

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1-[5-(4-Chloro-phen-yl)-3-(4-hy-droxy-phen-yl)-4,5-dihydro-1H-pyrazol-1-yl]-ethanone.

Project description:In the title compound, C(17)H(15)ClN(2)O(2), the benzene rings form dihedral angles of 89.56?(5) and 5.87?(5)° with the mean plane of the pyrazoline ring (r.m.s. deviation = 0.084?Å). The dihedral angle between the two benzene rings is 87.57?(5)°. In the crystal, mol-ecules are linked by O-H?O and C-H?O hydrogen bonds into a helical chain along the c axis. Between the chains weak C-H?N and C-H?O inter-actions are present. The crystal studied was an inversion twin with a domain ratio of 0.72?(4):0.28?(4).

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(5-Hy-droxy-3-methyl-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)(pyridin-4-yl)methanone monohydrate.

Project description:In the title compound, C(16)H(15)N(3)O(2)·H(2)O, the mean plane of the approximately planar pyrazole ring [maximum deviation = 0.0474?(18)?Å] makes dihedral angles of 86.32?(11) and 45.04?(10)° with the phenyl and pyridine rings, respectively. The dihedral angle between the phenyl and pyridine rings is 69.62?(11)°. In the crystal, inter-molecular O-H?O and O-H?N hydrogen bonds connect the components into chains along [010]. The crystal structure is further stabilized by ?-? stacking inter-actions with centroid-centroid distances of 3.7730?(12)?Å.

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