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5-(4-Fluoro-phen-yl)-3-(4-methyl-phen-yl)-4,5-dihydro-1H-pyrazole-1-carbothio-amide.

ABSTRACT: The central pyrazole ring in the title compound, C17H16FN3S, adopts an envelope conformation with the methine C atom bearing the 4-fluoro-phenyl substituent as the flap atom. Whereas the tolyl ring is slightly twisted out of the least-squares plane through the pyrazole ring [dihedral angle = 13.51?(11)°], the fluoro-benzene ring is almost perpendicular [dihedral angle = 80.21?(11)°]. The thio-amide group is almost coplanar with the N-N bond of the ring [N-N-C-N torsion angle = 1.2?(3)°] and the amine group forms an intra-molecular hydrogen bond with a ring N atom. In the crystal, supra-molecular double layers in the bc plane are formed via N-H?S, N-H?F and C-H?F inter-actions.

SUBMITTER: Abdel-Wahab BF

PROVIDER: S-EPMC3588501 | biostudies-other | 2013 Mar

REPOSITORIES: biostudies-other

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5-(4-Fluoro-phen-yl)-3-(4-methyl-phen-yl)-4,5-dihydro-1H-pyrazole-1-carbothio-amide.

Abdel-Wahab Bakr F BF Abdel-Wahab Bakr F BF Mohamed Hanan A HA Khidre Rizk E RE Ng Seik Weng SW Tiekink Edward R T ER

Acta crystallographica. Section E, Structure reports online 20130216 Pt 3

The central pyrazole ring in the title compound, C17H16FN3S, adopts an envelope conformation with the methine C atom bearing the 4-fluoro-phenyl substituent as the flap atom. Whereas the tolyl ring is slightly twisted out of the least-squares plane through the pyrazole ring [dihedral angle = 13.51 (11)°], the fluoro-benzene ring is almost perpendicular [dihedral angle = 80.21 (11)°]. The thio-amide group is almost coplanar with the N-N bond of the ring [N-N-C-N torsion angle = 1.2 (3)°] and the ...[more]

PMID: 23476571

Similar Datasets

5-(4-Fluoro-phen-yl)-3-[5-methyl-1-(4-methyl-phen-yl)-1H-1,2,3-triazol-4-yl]-4,5-dihydro-1H-pyrazole-1-carbothio-amide.

Project description:In the title compound, C(20)H(19)FN(6)S, the pyrazole ring has an envelope conformation, with the methine C atom being the flap atom. The dihedral angle between the least-squares plane through the pyrazole and triazole rings is 7.59?(9)°, and the triazole and attached benzene ring form a dihedral angle of 74.79?(9)°. The thio-urea group is coplanar with the pyrazole ring [N-N-C-S torsion angle = -179.93?(11)°], which enables the formation of an intra-molecular N-H?N hydrogen bond. In the crystal, inversion-related mol-ecules associate via N-H?S hydrogen bonds and eight-membered {?HNCS}(2) synthons feature in the crystal packing. These synthons are connected into supra-molecular chains along the a axis via N-H?F hydrogen bonds, and the chains are consolidated into layers in the ab plane via C-H?S and C-H?F contacts.

| S-EPMC3379505 | biostudies-literature

3-(4-Chloro-phen-yl)-5-(thio-phen-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothio-amide.

Project description:In the title pyrazoline derivative, C(14)H(12)ClN(3)S(2), the thiophene ring is disordered over two orientations with a refined site-occupancy ratio of 0.832 (4):0.168 (4). The pyrazoline ring adopts an envelope conformation with the C atom linking the thiophene ring at the flap. The dihedral angles between the benzene ring and the major and minor components of the thiophene ring are 88.6 (3) and 85.6 (15)°, respectively while the dihedral angle between the disorder components of the ring is 3.1 (16)°. The mean plane of the pyrazoline ring makes dihedral angles of 11.86 (13), 80.1 (3) and 83.0 (15)°, respectively, with the benzene ring, and the major and minor components of the thiophene ring. An intra-molecular N(amide)-H⋯N(pyrazoline) hydrogen bond generates an S(5) ring motif. In the crystal, mol-ecules are linked by weak C-H⋯S and N(amide)-H⋯S inter-actions into a tape along [10[Formula: see text]]. C-H⋯π inter-actions are also observed.

| S-EPMC3274952 | biostudies-literature

4-[(2,4-Difluoro-phen-yl)hydrazinyl-idene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazole-1-carbothio-amide.

Project description:In the title compound, C(11)H(9)F(2)N(5)OS, the pyrazole ring forms a dihedral angle of 16.42?(6)° with the benzene ring. Intra-molecular N-H?O hydrogen bonds generate two S(6) ring motifs. In the crystal, an R(2) (2)(8) ring motif is formed by a pair of inter-molecular N-H?S hydrogen bonds. Inter-molecular C-H?F hydrogen bonds further link the mol-ecules into a three-dimensional network.

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4-[2-(4-Bromo-phen-yl)hydrazinyl-idene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazole-1-carbothio-amide.

Project description:In the title compound, C(11)H(10)BrN(5)OS, the approximately planar pyrazole ring [maximum deviation = 0.014?(2)?Å] forms a dihedral angle of 5.49?(13)° with the benzene ring. An intra-molecular N-H?O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked through inter-molecular N-H?S and N-H?O hydrogen bonds, forming a two-dimensional network parallel to (100). A short Br?Br contact of 3.5114?(6)?Å is also observed.

| S-EPMC3201347 | biostudies-literature

4-[2-(4-Chloro-phen-yl)hydrazinyl-idene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazole-1-carbothio-amide.

Project description:In the title mol-ecule, C(11)H(10)ClN(5)OS, an intra-molecular N-H?O hydrogen forms an S(6) ring motif. The dihedral angle between the pyrazole ring and the benzene ring is 3.77?(8)°. In the crystal, mol-ecules are linked by N-H?S and N-H?O hydrogen bonds into layers parallel to the bc plane.

| S-EPMC3201496 | biostudies-literature

3-(4-Chloro-phen-yl)-5-(4-fluoro-phen-yl)-4,5-dihydro-1H-pyrazole-1-carbothio-amide.

Project description:In the title compound, C16H13ClFN3S, the pyrazole ring adopts an envelope conformation with the methine C atom being the flap atom. The chloro- and fluoro-benzene rings are twisted out of the plane of the pyrazole ring [dihedral angles = 15.12?(11) and 80.55?(10)°, respectively]. The amine group is orientated towards a ring N atom, forming an intra-molecular N-H?N hydrogen bond. This H atom also forms a hydrogen bond to the F atom, which along with N-H?S hydrogen bonding leads to a supra-molecular chain along the c axis. Connections between chains of the type Cl?? lead to a layer in the bc plane.

| S-EPMC3588515 | biostudies-other

5-(4-Meth-oxy-phen-yl)-3-(pyridin-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothio-amide.

Project description:In the title compound, C(16)H(16)N(4)OS, the dihedral angle between the pyridine and benzene rings is 81.08?(6)°. The pyrazole ring makes dihedral angles of 12.36?(7) and 87.96?(6)°, respectively, with the pyridine and benzene rings. In the crystal, mol-ecules are linked by N-H?O and N-H?S hydrogen bonds and a weak C-H?S inter-action into a layer parallel to the ab plane. Weak C-H?? and ?-? inter-actions [centroid-centroid distances = 3.7043?(9) and 3.8120?(7)?Å] are also observed.

| S-EPMC3239124 | biostudies-literature

3-Methyl-4-[2-(4-nitro-phen-yl)hydrazin-1-yl-idene]-5-oxo-4,5-dihydro-1H-pyrazole-1-carbothio-amide.

Project description:The asymmetric unit of the title compound, C(11)H(10)N(6)O(3)S, contains two independent mol-ecules, each of which is stabilized by an intra-molecular N-H⋯O hydrogen bond, forming an S(6) ring motif. In one mol-ecule, the pyrazole ring forms a dihedral angle of 10.93 (14)° with the benzene ring. The corresponding dihedral angle in the other mol-ecule is 7.03 (14)°. In the crystal, mol-ecules are linked via pairs of (N,N)-H⋯O bifurcated acceptor bonds which, together with C-H⋯O hydrogen bonds, form sheets parallel to (001).

| S-EPMC3393969 | biostudies-literature

4-[2-(2-Meth-oxy-phen-yl)hydrazinyl-idene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazole-1-carbothio-amide.

Project description:In the title mol-ecule, C(12)H(13)N(5)O(2)S, a bifurcated intra-molecular N-H?O(O) hydrogen bond forms two S(6) ring motifs. The benzene ring forms a dihedral angle of 14.36?(11)° with the pyrazole ring. In the crystal, pairs of N-H?S hydrogen bonds form centrosymmetric dimers, generating R(2) (2)(8) ring motifs, which stack along the b axis.

| S-EPMC3201502 | biostudies-literature

3-(4-Chloro-phen-yl)-5-(4-eth-oxy-phen-yl)-4,5-dihydro-1H-pyrazole-1-carbothio-amide ethanol monosolvate.

Project description:The asymmetric unit of the title compound, C18H18ClN3OS·C2H5OH, comprises a pyrazoline derivative and an ethanol solvent mol-ecule. In the mol-ecule of the pyrazoline derivative, the pyrazole ring adopts an envelope conformation with the C atom bearing the eth-oxy-phenyl substituent as the flap. The dihedral angle between the benzene rings is 74.22?(7)°. The eth-oxy group is coplanar with the attached benzene ring [C-O-C-Cmeth-yl = 175.50?(11)° and r.m.s. deviation = 0.0459?(1)?Å for the nine non-H atoms]. In the crystal, the pyrazoline mol-ecules are linked by N-H?Oeth-oxy hydrogen bonds into chains along the c axis and are further linked with the solvent ethanol mol-ecules by N-H?Oethanol and Oethanol-H?S hydrogen bonds. C-H?? inter-actions are also present.

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