Crystal structures of three carbazole derivatives: 12-ethyl-7-phenyl-sulfonyl-7H-benzofuro[2,3-b]carbazole, (1), 2-(4,5-dimeth-oxy-2-nitro-phen-yl)-4-hy-droxy-9-phenyl-sulfonyl-9H-carbazole-3-carbaldehyde, (2), and 12-phenyl-7-phenyl-sulfonyl-7H-benzofuro[2,3-b]carbazole, (3).

The three title compounds, C26H19NO3S, (1), C27H20N2O8S, (2), and C30H19NO3S, (3), are carbazole derivatives, where (1) and (3) are heterocycle-containing carbazoles with a benzo-furan moiety fused to a carbazole unit. In (2), a di-meth-oxy-nitro-phenyl ring is attached to the carbazole moiety. In the three derivatives, a phenyl-sulfonyl group is attached to the N atom of the carbazole unit. Compound (1) crystallizes with two independent mol-ecules in the asymmetric unit (A and B). The carbazole skeleton in the three compounds is essentially planar. In compound (1), the benzene ring of the phenyl-sulfonyl moiety is almost orthogonal to the carbazole moiety, with dihedral angles of 85.42 (9) and 84.52 (9)° in mol-ecules A and B, respectively. The benzene ring of the phenyl-sulfonyl group in compounds (2) and (3) are inclined to the carbazole moiety, making dihedral angles of 70.73 (13) and 81.73 (12)°, respectively. The S atom has a distorted tetra-hedral configuration in all three compounds. In the crystals, C-H⋯O hydrogen bonds give rise to R22(12) inversion dimers for compound (1), and to R22(24) inversion dimers and R44(40) ring motifs for compound (2). The crystal packing in (1) also features C-H⋯π and π-π inter-actions [shortest inter-centroid distance = 3.684 (1) Å], leading to supra-molecular three-dimensional aggregation. In the crystal of compound (2), the combination of the various C-H⋯O hydrogen bonds leads to the formation of a three-dimensional network. In the crystal of compound (3), mol-ecules are linked by C-H⋯O hydrogen bonds, forming chains running parallel to the a axis, and the chains are linked by C-H⋯π inter-actions, forming corrugated sheets parallel to the ab plane.

Crystal structure of 3-[(E)-(2-hy-droxy-3-meth-oxy-benzyl-idene)amino]-1-methyl-1-phenyl-thio-urea.

In the asymmetric unit of the title compound, C16H17N3O2S, there are two independent mol-ecules (A and B), which show an E conformation with respect to the C=N bond. An intra-molecular O-H⋯N hydrogen bond with an S(6) motif stabilizes the mol-ecular structure. The terminal phenyl and benzene rings are almost orthogonal to each other, the dihedral angle being 87.47 (13)° for mol-ecule A and 89.86 (17)° for mol-ecule B. In the crystal, weak bifurcated N-H⋯(O,O) hydrogen bonds link the two independent mol-ecules, forming a supra-molecular chain with a C (2) 1(14)[R (2) 1(5)] motif along the b axis. A weak C-H⋯O inter-action is also observed in the chain.

Crystal structures of two hydrazinecarbo-thio-amide derivatives: (E)-N-ethyl-2-[(4-oxo-4H-chromen-3-yl)methyl-idene]hydrazinecarbo-thio-amide hemi-hydrate and (E)-2-[(4-chloro-2H-chromen-3-yl)methyl-idene]-N-phenyl-hydrazinecarbo-thio-amide.

The title compounds, C13H13N3O2S·0.5H2O, (I), and C17H14ClN3OS, (II), are hydrazinecarbo-thio-amide derivatives. Compound (I) crystallizes with two independent mol-ecules (A and B) and a water mol-ecule of crystallization in the asymmetric unit. The chromene moiety is essentially planar in mol-ecules A and B, with maximum deviations of 0.028 (3) and 0.016 (3) Å, respectively, for the carbonyl C atoms. In (II), the pyran ring of the chromene moiety adopts a screw-boat conformation and the phenyl ring is inclined by 61.18 (9)° to its mean plane. In the crystal of (I), bifurcated N-H⋯O and C-H⋯O hydrogen bonds link the two independent mol-ecules forming A-B dimers with two R 2 (1)(6) ring motifs, and R 2 (2)(10) and R 2 (2)(14) ring motifs. In addition to these, the water mol-ecule forms tetra-furcated hydrogen bonds which alternately generate R 4 (4)(12) and R 6 (6)(22) graph-set ring motifs. There are also π-π [inter-centroid distances = 3.5648 (14) and 3.6825 (15) Å] inter-actions present, leading to the formation of columns along the c-axis direction. In the crystal of (II), mol-ecules are linked by pairs of N-H⋯S hydrogen bonds, forming inversion dimers with an R 2 (2)(8) ring motif. The dimers are linked by C-H⋯π inter-actions, forming ribbons lying parallel to (210).

Crystal structure of (E)-2-[(4-chloro-2H-chromen-3-yl)methyl-idene]-N-cyclo-hexyl-hydrazinecarbo-thio-amide.

In the title compound, C17H20ClN3OS, the mean plane of the central thio-urea core makes dihedral angles of 26.56 (9) and 47.62 (12)° with the mean planes of the chromene moiety and the cyclo-hexyl ring, respectively. The cyclo-hexyl ring adopts a chair conformation. The N-H atoms of the thio-urea unit adopt an anti conformation. The chromene group is positioned trans, whereas the cyclo-hexyl ring lies in the cis position to the thione S atom, with respect to the thio-urea C-N bond. In the crystal, mol-ecules are linked by N-H⋯S hydrogen bonds, forming inversion dimers enclosing R (2) 2(8) ring motifs. The dimers are linked by C-H⋯Cl hydrogen bonds, enclosing R (6) 6(44) ring motifs, forming sheets lying parallel to (010).

Methyl 4-(4-bromo-anilino)-2',5-dioxo-5H-spiro-[furan-2,3'-indoline]-3-carboxyl-ate.

In the title compound, C19H13BrN2O5, the spiro furan ring is almost planar with a maximum deviation of 0.034 (2) Å. The indole unit and the furan ring are normal to each other, making a dihedral angle of 87.82 (8) °. The mol-ecular structure is stabilized by an intra-molecular N-H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, mol-ecules are linked via pairs of N-H⋯O hydrogen bonds, forming inversion dimers enclosing R (2) 2(8) ring motifs.

Methyl 4-anilino-2',5-dioxo-1',2'-di-hydro-5H-spiro-[furan-2,3'-indole]-3-carboxyl-ate.

In the title compound, C19H14N2O5, the spiro junction links an oxindole moeity and a furan ring, which subtend a dihedral angle of 83.49 (6)°. The mol-ecular structure features an N-H⋯O hydrogen bond, which generates an S(6) ring motif. The crystal packing is governed by two N-H⋯O inter-actions, one of which generates a centrosymmetric R 2 (2)(14) dimer. The other N-H⋯O inter-action along with a C-H⋯O hydrogen bond contributes to the formation of a C 2 (2)[R 2 (2)(9)] dimeric chain running along the b-axis direction.

(Z)-Methyl 2-[(2-eth-oxy-6-formyl-phen-oxy)meth-yl]-3-(4-ethyl-phen-yl)acrylate.

The title compound, C(22)H(24)O(5), consists of two substituted benzene rings linked by an ethyl acrylate group. The dihedral angle between the two benzene rings is 58.39 (7)°. The crystal packing is governed by two C-H⋯O inter-actions, one of which forms centrosymmetric dimers with a graph-set descriptor of R(2) (2)(18).

(Z)-Methyl 3-(2,4-dichloro-phen-yl)-2-[(2-formyl-phen-oxy)meth-yl]acrylate.

In the title compound, C(18)H(14)Cl(2)O(4), the mean planes of the methyl acrylate unit and the phenyl ring of the benzaldehyde are approximately orthogonal to each other, making a dihedral angle of 83.31 (6)°. The O atom of the aldehyde group is displaced significantly from the phenyl ring plane by 0.226 (2) Å. The methyl acrylate group adopts an E conformation. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds generate R(2) (2)(24) loops.

1-Methyl-3-p-tolyl-3,3a,4,9b-tetra-hydro-1H-chromeno[4,3-c]isoxazole-3a-carbonitrile.

In the title compound, C(19)H(18)N(2)O(2), the dihedral angle between the mean planes of the fused chromeno and isoxazole units is 43.71 (7)°. The isoxazole and pyran rings exhibit envelope and half chair conformations, respectively. The crystal packing is stabilized by inter-molecular C-H⋯π inter-actions.

1-Methyl-3-(naphthalen-1-yl)-3,3a,4,9b-tetra-hydro-1H-chromeno[4,3-c]isoxazole-3a-carbonitrile.

In the title compound, C(22)H(18)N(2)O(2), the pyran ring of the chromene unit is fused with an isoxazole ring, which adopts an N-envelope conformation with the N atom lying 1.3291 (14) Šfrom the mean plane of the remaining ring atoms [maximum deviation = 0.341 (2) Å]. The dihedral angle between the isoxazole and chromene units is 43.74 (8)° and that between the iosxazole ring and the naphthalene ring system is 58.82 (8)°. In the crystal, the molecules are linked by weak C-H⋯π inter-actions.

3'-Hy-droxy-methyl-1'-methyl-3'-nitro-4'-(o-tol-yl)spiro-[indoline-3,2'-pyrrolidin]-2-one.

The title compound, C(20)H(21)N(3)O(4), crystallizes with two mol-ecules in the asymmetric unit. In both mol-ecules, the pyrrolidine ring adopts an envelope conformation. The crystal structure is stabilized by inter-molecular C-H⋯O, N-H⋯O and O-H⋯O hydrogen bonds.