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In the title compound, C22H19N5OS·H2O, the naphthalene ring system and the benzene ring [dihedral angle = 85.19 (8)°] make dihedral angles of 87.02 (9) and 14.41 (10)°, respectively, with the pyrazole ring. The mean plane through the 2-methyl­enehydrazinecarbothio­amide group [C—N—N—C(=S)—N; maximum deviation = 0.022 (1) Å] is slightly twisted from the pyrazole ring [dihedral angle = 5.60 (11)°]. In the crystal, mol­ecules are linked by N—H⋯S, N—H⋯O, O—H⋯S, O—H⋯N and C—H⋯S hydrogen bonds into sheets parallel to the ab plane. π–π inter­actions are also observed [centroid-to-centroid distances = 3.7778 (12) and 3.7010 (12) Å].

In the title compound, C18H17N5OS, the mean plane of the pyrazole ring [maximum deviation = 0.0031 (12) Å] forms dihedral angles of 19.6 (4) and 9.3 (5)° with the two disorder components of the N-bound benzene ring (with equal occupancies for the two orientations) and a dihedral angle of 72.58 (8)° with the C—O-bonded benzene ring. The mol­ecule exists in a trans conformation with respect to the N=C bond [1.2792 (19) Å]. The mol­ecular structure features an intra­molecular C—H⋯O hydrogen bond, forming an S(6) ring. In the crystal, N—H⋯N and N—H⋯S hydrogen bonds result in the formation of zigzag layers lying parallel to (10-1).

In the title compound, C19H13BrO3S, the 4-bromo­phenyl ring makes a dihedral angle of 64.11 (2)° with the mean plane [r.m.s. deviation = 0.01 (2) Å] of the naphtho­furan ring. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯π inter­actions. The crystal structure also exhibits slipped π–π inter­actions between the central naphtho­furan benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.559 (2), slippage = 1.036 (2) Å], and between the central naphtho­furan benzene ring and the furan ring of neighbouring mol­ecules [centroid–centroid distance = 3.655 (2), slippage = 1.136 (2) Å].

In the title compound, C20H16O2S, the 4-methyl­phenyl ring makes a dihedral angle of 82.60 (4)° with the mean plane [r.m.s. deviation = 0.007 (1) Å] of the naphtho­furan fragment. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O hydrogen bonds, and by a slipped π–π inter­action between the central naphtho­furan benzene rings of neighbouring mol­ecules [centroid-to-centroid distance = 3.671 (2) Å, inter­planar distance = 3.349 (2) Å and slippage = 1.503 (2)°].

In the title compound, C19H13BrO2S, the 4-bromo­phenyl ring makes a dihedral angle of 83.75 (4)° with the mean plane of the naphtho­furan fragment [r.m.s. deviation = 0.024 (2) Å]. In the crystal, mol­ecules are linked via pairs of C—H⋯O hydrogen bonds, forming inversion dimers. These dimers are connected by weak π–π inter­actions between the central naphtho­furan benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.483 (2) Å, inter­planar distance = 3.416 (2) Å and slippage = 0.680 (2) Å].

The complete mol­ecule of the title compound, C42H36N6O2, is generated by a crystallographic twofold axis with two C atoms of the central phenyl group lying on the axis. In the independent part of the mol­ecule, one amino group is involved in an intra­molecular N—H⋯O hydrogen bond, and the two adjacent phenyl rings are twisted from the plane of the pyrazolone ring with dihedral angles of 6.82 (3) and 88.32 (6)°. The crystal packing exhibits no classical inter­molecular contacts.

The mol­ecule of the title compound, C23H18Cl2N4O, assumes a non-planar conformation in which the pyrazolone ring forms dihedral angles of 32.61 (19), 76.73 (14) and 52.57 (19)° with the three benzene rings. The secondary amino group is involved in an intra­molecular N—H⋯O hydrogen bond. In the crystal, mol­ecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers. An offset stacking inter­action is observed between the chloro-substituted benzene rings protruding on both sides of these dimers [centroid–centroid distance = 3.862 (1) Å].

In the title compound, C20H21N3O2S, 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 mol­ecular conformation is consolidated by an intra­molecular C—H⋯O hydrogen bond, which forms an S(6) ring. In the crystal, inversion dimers linked by pairs of N—H⋯Op (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).

In the title compound, C19H12BrFO3S, the 3-fluoro­phenyl ring makes a dihedral angle of 80.85 (5)° with the mean plane [r.m.s. deviation = 0.009 (2)Å] of the naphtho­furan fragment. In the crystal, mol­ecules are linked by slipped π–π inter­actions between the furan and the outer benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.756 (3) Å and slippage of 1.189 (3) Å].

The title compound, C21H23N3O, exists in an enamine–keto form with the amino group involved in an intra­molecular N—H⋯O hydrogen bond. The dihedral angle between the phenyl rings is 73.59 (6)°. The five-membered ring is nearly planar, the largest deviation being 0.0004 (7) Å, and makes dihedral angles of 4.81 (6) and 69.81 (5)° wth the phenyl rings. In the crystal, pairs of weak C—H⋯O inter­actions link the mol­ecules into centrosymmetric dimers.

In the mol­ecule of the title compound, C18H16N4O, the intra­molecular N—H⋯N hydrogen bond results in the formation of a planar five-membered ring, which is also co-planar with the adjacent five-membered ring, being oriented at a dihedral angle of 1.23 (3)°. The dihedral angles formed by the planar pyrazole ring with the adjacent phenyl ring and the other phenyl ring are 7.29 and 11.21°, respectively. The dihedral angle between the two phenyl rings is 18.07°. In the crystal structure, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules.

The mol­ecule of the title compound, C23H20N4O, assumes a non-planar conformation in which the pyrazolone ring forms dihedral angles of 10.33 (11), 65.34 (11) and 63.52 (10)° with the three benzene rings. In the crystal, the mol­ecules are linked by inter­molecular N—H⋯N hydrogen bonds, generating chains parallel to the b axis. The secondary amino group is involved in an intra­molecular N—H⋯O hydrogen bond.

In the mol­ecule of the title compound, C22H20ClN5O, the atoms of the two pyrazole rings and the –C=N– group which joins them are essentially coplanar, with an r.m.s. deviation of 0.054 (2) Å. The phenyl rings form dihedral angles of 41.24 (5) and 55.53 (5)° with this plane. The crystal structure is stabilized by weak inter­molecular π–π inter­actions, with centroid-to-centroid distances of 3.6179 (13) Å between the imidazole rings.

The title compound, C23H18ClN3O, exists in an enamine–keto form with the amino group involved in an intra­molecular 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 mol­ecules into supra­molecular chains along the b axis.

The title Schiff base compound, C23H23N5O, was synthesized by the reaction of 4-amino­phenazone and 3,5-dimethyl-1-phenyl­pyrazole-4-carbaxaldehyde. The mol­ecule adopts an E configuration about the central C=N double bond. A weak intra­molecular C—H⋯O hydrogen bond generates an S(6) ring motif. The dihedral angle between the pyrazole rings is 24.72 (10)° and the dihedral angles between the pyrazole rings and the adjacent phenyl rings are 58.67 (10) and 46.58 (11)°. The crystal structure is stabilized by weak C—H⋯π inter­actions involving the pyrazolone and phenyl rings.

In the title compound, C16H15N3O2·H2O, 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, inter­molecular O—H⋯O and O—H⋯N hydrogen bonds connect the components into chains along [010]. The crystal structure is further stabilized by π–π stacking inter­actions with centroid–centroid distances of 3.7730 (12) Å.

In the title compound, C15H14N2O3, the furan ring is disordered over two positions with a refined site-occupancy ratio of 0.587 (11):0.413 (11). The mean plane of the approximately planar pyrazole ring [maximum deviation = 0.0469 (11) Å] makes dihedral angles of 86.13 (11) and 4.5 (5)° with the phenyl and furan rings, respectively. The dihedral angle between the phenyl ring and the major component of the disordered furan ring is 81.8 (5)°. The mol­ecule shows chirality in one of the carbon atoms but the centrosymmetric space group means the compound is a racemic mixture. In the crystal, inter­molecular O—H⋯O and C—H⋯O hydrogen bonds connect the mol­ecules. The crystal structure is further stabilized by π–π stacking inter­actions with a centroid–centroid distance of 3.8646 (12) Å.

In the title compound, C11H11N5OS, the pyrazole ring is approximately planar, with a maximum deviation of 0.010 (2) Å. The dihedral angles between the benzene ring and the pyrazole and carbothio­amide groups are 5.42 (9) and 10.61 (18)°, respectively. An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are connected by inter­molecular N—H⋯O and C—H⋯S hydrogen bonds, forming R 2 2(12) ring motifs. In addition, there is a π–π stacking inter­action [centroid–centroid distance = 3.5188 (11) Å] between the pyrazole and benzene rings. These inter­actions link the mol­ecules into infinite chains along [001].

The title compound, C19H13ClO3S, was prepared by the oxidation of 3-(4-chloro­phenyl­sulfan­yl)-2-methyl­naphtho[1,2-b]furan with 3-chloro­peroxy­benzoic acid. The 4-chloro­phenyl ring makes a dihedral angle of 68.59 (5)° with the plane of the naphthofuran fragment. The crystal structure is stabilized by π–π inter­actions between the benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.635 (3) Å], and by C—H⋯π inter­actions between a methyl H atom and the furan ring of an adjacent mol­ecule. In addition, the crystal structure exhibits inter­molecular C—H⋯O inter­actions.

In the title compound, C21H17N3O4·H2O, the coumarin ring system is almost planar (r.m.s. deviation = 0.002 Å) and makes dihedral angles of 1.50 (7) and 57.75 (7)° with the pyrazole and phenyl rings, respectively. The dihedral angle between the pyrazole and phenyl rings is 56.60 (9)°. The pyrazole ring adopts a twisted comformation. The mol­ecular conformation is stabilized by intra­molecular N—H⋯O and C—H⋯O hydrogen bonds, both of which form S(6) ring motifs. In the crystal, each water mol­ecule is linked to its adjacent organic mol­ecule via pairs of O—H⋯O hydrogen bonds. The packing is further consolidated by pairs of inter­molecular C—H⋯O hydrogen bonds, which link the mol­ecules into dimers; the dimers are stacked along the b axis.

In the title compound, C18H18ClN5O3, the hydrazinecarboxamide N—N—C(O)—N unit is nearly planar [maximum deviation = 0.074 (2) Å] and is inclined at a dihedral angle of 57.43 (7)° with respect to the plane of the attached benzene ring. The chloro­phenyl group makes dihedral angles of 19.71 (7) and 34.07 (6)° with the pyrazole and benzene rings, respectively. In the crystal, pairs of N—H⋯O hydrogen bonds link the mol­ecules into inversion dimers that are further linked into chains along the a-axis direction by N—H⋯N hydrogen bonds. In addition, π–π stacking inter­actions are observed between benzene rings [centroid–centroid distance = 3.680 (1) Å].

In the title compound, C10H16N2O·H2O, the cyclo­hexane ring is in a chair conformation and its least-squares plane makes a dihedral angle of 53.68 (5)° with the approximately planar pyrazole ring [maximum deviation = 0.034 (1) Å]. Pairs of inter­molecular N—H⋯O hydrogen bonds form inversion dimers between neighbouring pyrazolone mol­ecules, generating R 2 2(8) ring motifs. The pyrazolone and water mol­ecules are further linked by inter­molecular N—H⋯O, C—H⋯O and O—H⋯O hydrogen bonds into two-dimensional sheets parallel to the bc plane.

The title compound, C19H14O3S, was prepared by the oxidation of 2-methyl-1-(phenyl­sulfan­yl)naphtho[2,1-b]furan with 3-chloro­peroxy­benzoic acid. The phenyl ring makes a dihedral angle of 87.13 (4)° with the plane of the naphthofuran fragment. The crystal structure is stabilized by π–π inter­actions between the furan and benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.850 (2) Å] and weak C—H⋯π inter­actions. In addition, there are also intra­molecular C—H⋯O inter­actions.

The title compound, C19H13BrO3S, was prepared by the oxidation of 7-bromo-2-methyl-1-(phenyl­sulfan­yl)naph­tho[2,1-b]furan with 3-chloro­peroxy­benzoic acid. The phenyl ring makes a dihedral angle of 80.4 (2)° with the plane of the naphthofuran fragment. The crystal structure is stabilized by aromatic π–π stacking inter­actions between the brominated benzene ring and the central benzene ring of the naphthofuran system of neighbouring mol­ecules; the centroid–centroid distances within the stack are 3.889 (3) and 3.981 (3) Å. In addition, the stacked mol­ecules exhibit C—H⋯π, inter- and intra­molecular C—H⋯O inter­actions.

The mol­ecule of the title compound, C27H22N4O, assumes a non-planar conformation in which the pyrazolone ring forms dihedral angles of 12.73 (11), 65.17 (6) and 49.82 (6)°, respectively, with the two benzene rings and the naphthalene ring system. In the crystal, pairs of mol­ecules are linked by inter­molecular N—H⋯N hydrogen bonds, forming dimers. The secondary amino group is involved in an intra­molecular N—H⋯O hydrogen bond.