(1E,2E)-1,2-Bis[1-(3-nitro-phen-yl)ethyl-idene]hydrazine.

The asymmetric unit of the title compound, C(16)H(14)N(4)O(4), contains one half-mol-ecule of (nitro-phen-yl)ethanimine and the complete mol-ecule is generated by a crystallographic inversion centre. The mol-ecule has an E conformation with respect to each C=N double bond. The central C=N-N=C plane is twisted from the benzene rings with a dihedral angle of 24.76 (11)°. In the crystal, C-H⋯O inter-actions link the molecules to form sheets that lie parallel to (10-4).

(E)-1-[4-(Hex-yloxy)phen-yl]-3-(2-hy-droxy-phen-yl)prop-2-en-1-one.

In the title compound, C(21)H(24)O(3), the enone moiety adopts an s-cis conformation and the dihedral angle between the benzene rings is 12.89 (6)°. The hex-yloxy tail adopts an extended conformation. In the crystal, inversion dimers are linked by pairs of O-H⋯O hydrogen bonds and pairs of C-H⋯O inter-actions, forming two R(2) (2)(7) and one R(2) (2)(10) loops. The dimers are then arranged into sheets lying parallel to (201) and weak C-H⋯π inter-actions consolidate the packing.

(E)-1-(3-Hy-droxy-phen-yl)-3-[4-(tetra-dec-yl-oxy)phen-yl]prop-2-en-1-one.

In the title compound, C(29)H(40)O(3), the enone moiety adopts an s-cis conformation. The dihedral angle between the benzene rings is 4.33 (5)° The least-squares mean line through the tetra-decyl side chain forms a dihedral angle of 83.99 (7)° with the normal to the attached benzene ring. In the crystal, O-H⋯O and C-H⋯O hydrogen bonds involving the keto and the hy-droxy O atoms form ribbons along [-41-1]. The crystal structure also features C-H⋯π inter-actions.

(E)-1-(4-Decyl-oxyphen-yl)-3-(2-hy-droxy-phen-yl)prop-2-en-1-one.

In the title compound, C(25)H(32)O(3), the enone group adopts an s-cis conformation. The alk-oxy chain is in an all-trans conformation. The dihedral angle between the benzene rings is 7.86 (5)°. In the crystal, mol-ecules are connected by pairs of O-H⋯O hydrogen bonds, forming inversion dimers and giving R(2) (2)(10) rings. Within these dimers, weak C-H⋯O hydrogen bonds form two R(2) (2)(7) rings. In the crystal, the approximately planar mol-ecules [largest deviation for an atom being 0.4737 (12) Šfor the terminal C atom of the alk-oxy chain] are arranged in sheets parallel to (20-1). Weak C-H⋯π inter-actions are also observed.

Ethyl 2-(1,3-benzodioxol-5-yl)-1-[3-(1H-imidazol-1-yl)prop-yl]-1H-benzimidazole-5-carboxyl-ate.

In the title compound, C(23)H(22)N(4)O(4), the essentially planar [maximum deviation = 0.022 (1) Å] benzimidazole ring system forms dihedral angles of 86.16 (7) and 37.38 (6)°, respectively, with the imidazole and benzene rings. The dioxolane ring adopts an envelope conformation with the methyl-ene C atom at the flap. In the crystal, C-H⋯O and C-H⋯N inter-actions link the mol-ecules into a ribbon along the a axis. The crystal packing is further stabilized by weak π-π stacking inter-actions [centroid-centroid distances = 3.5954 (8) and 3.7134 (8) Å] and C-H⋯π inter-actions.

Ethyl 2-(4-nitro-phen-yl)-1-[3-(2-oxopyrrolidin-1-yl)prop-yl]-1H-benzimidazole-5-carboxyl-ate.

In the title compound, C(23)H(24)N(4)O(5), the essentially planar benzimidazole ring system [maximum deviation = 0.008 (2) Å] forms a dihedral angle of 39.22 (7)° with the attached nitro-benzene ring. The pyrrolidin-2-one ring adopts an envelope conformation with a C atom as the flap. In the crystal, mol-ecules are connected by C-H⋯O inter-actions, forming sheets propagating in (011). The crystal packing also features weak π-π stacking inter-actions [centroid-centroid = 3.6746 (12) Å].

Ethyl 2-(4-hy-droxy-3-meth-oxy-phen-yl)-1-[3-(2-oxopyrrolidin-1-yl)prop-yl]-1H-benzimidazole-5-carboxyl-ate monohydrate.

In the title compound, C(24)H(27)N(3)O(5)·H(2)O, the essentially planar benzimidazole ring system [maximum deviation = 0.020 (1) Å] forms dihedral angles of 54.10 (11) and 67.79 (6)°, respectively, with the mean plane of pyrrolidin-2-one ring and the benzene ring. The pyrrolidin-2-one ring adopts an envelope conformation with one of the methylene C atoms at the flap. An intra-molecular C-H⋯π inter-action is observed. In the crystal, O-H⋯O and O-H⋯N hydrogen bonds link the two components into a double-tape structure along the a axis. The crystal packing is further stabilized by weak π-π stacking [centroid-centroid distance = 3.6632 (9) Å] and C-H⋯O inter-actions.

Ethyl 1-[3-(2-oxopyrrolidin-1-yl)prop-yl]-2-phenyl-1H-benzimidazole-5-carboxyl-ate.

In the title compound, C(23)H(25)N(3)O(3), the benzimidazole ring system is essentially planar [maximum deviation = 0.0240 (18) Å]. The mean plane through this ring system forms a dihedral angle of 42.23 (7)° with the benzene ring. The pyrrolidine ring is in an envelope conformation with the flap atom disordered over two sites with occupancies of 0.813 (11) and 0.187 (11). In the crystal, weak C-H⋯O hydrogen bonds form R(2) (2)(10) ring motifs, which are connected by further C-H⋯O inter-actions, forming ribbons along the b axis. The crystal structure is further stabilized by weak π-π inter-actions involving the imidazole and benzene rings of the benzimidazole ring system [centroid-centroid distances = 3.6788 (11) and 3.6316 (10) Å] and weak C-H⋯π inter-actions.

Ethyl 2-(4-meth-oxy-phen-yl)-1-[3-(2-oxopyrrolidin-1-yl)prop-yl]-1H-benzimidazole-5-carboxyl-ate.

The asymmetric unit of the title compound, C(24)H(27)N(3)O(4), contains two mol-ecules, A and B. The benzimidazole rings are essentially planar [maximum deviations = 0.0144 (10) and 0.0311 (8) Šin A and B, respectively]. The dihedral angle between the benzimidazole mean plane and its attached benzene ring is 36.90 (5) ° for mol-ecule A and 51.40 (5) ° for mol-ecule B. In both mol-ecules, the pyrrolidine ring adopts an envelope conformation with a C atom as the flap. In molecule B, the flap C atom is disordered over two positions in a 0.711 (6):0.289 (6) ratio. In the crystal, C-H⋯O inter-actions link the mol-ecules, generating [100] chains. The crystal packing also features weak π-π inter-actions between the imidazole and benzene rings [centroid-centroid distances = 3.8007 (7) and 3.8086 (7) Å] and between the benzene rings [centroid-centroid distance = 3.7001 (7) Å] and C-H⋯π inter-actions involving the benzene rings.

Ethyl 2-(1,3-benzodioxol-5-yl)-1-[3-(2-oxopyrrolidin-1-yl)prop-yl]-1H-benz-imidazole-5-carboxyl-ate.

In the title compound, C(24)H(25)N(3)O(5), the benzimidazole and benzodioxole ring systems are each approximately planar [maximum deviations = 0.043 (1) and 0.036 (1) Å, respectively]. Their mean planes form a dihedral angle of 42.85 (4)°. The pyrrolidine ring has an envelope conformation with one of the methyl-ene C atoms forming the flap. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network. The crystal packing is further stabillized by weak π-π inter-actions between the benzene rings within the benzimidazole ring system [centroid-centroid distance = 3.7955 (7) Å]. A weak C-H⋯π inter-action involving the benzodioxole ring is also present.

2-(4-Bromo-phen-yl)-2-oxoethyl anthracene-9-carboxyl-ate.

In the title compound, C(23)H(15)BrO(3), the anthracene ring system is essentially planar [maximum deviation = 0.29 (2) Å] and makes a dihedral angle of 5.74 (8)° with the mean plane of the bromo-substituted benzene ring. An intra-molecular C-H⋯O hydrogen bond generates an S(9) ring motif. In the crystal, mol-ecules are linked by C-H⋯O inter-actions, forming a two-dimensional network parallel to the ac plane. π-π stacking inter-actions are observed between benzene rings [centroid-centroid distances = 3.5949 (14) and 3.5960 (13) Å].

4-(Morpholin-4-yl)-3-(trifluoro-meth-yl)-benzonitrile.

In the title benzonitrile compound, C(12)H(11)F(3)N(2)O, an intra-molecular C-H⋯F hydrogen bond generates an S(7) ring motif. The trifluoro-methyl group is disordered over two orientations with a refined occupancy ratio of 0.549 (16):0.451 (16). The morpholine ring adopts a chair conformation. The benzene ring and mean plane of the morpholine ring make a dihedral angle of 58.04 (10)° with each other. In the crystal, mol-ecules are connected by inter-molecular C-H⋯F and C-H⋯O inter-actions to form R(2) (2)(8) ring motifs. These inter-actions also link the mol-ecules into chains parallel to the [10[Formula: see text]] direction.

2-(4-Chloro-phen-yl)-2-oxoethyl 2-meth-oxy-benzoate.

In the title compound, C(16)H(13)ClO(4), the two benzene rings make a dihedral angle of 86.38 (8)°. In the crystal, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules to form columns along the a axis. The mol-ecules are also stabilized by a π-π stacking inter-action, with a centroid-centroid distance of 3.7793 (10) Šbetween the inversion-related benzene rings.

3-Methyl-5-oxo-4-(2-phenyl-hydrazinyl-idene)-4,5-dihydro-1H-pyrazole-1-carbothio-amide.

In the title compound, C(11)H(11)N(5)OS, 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 carbothio-amide groups are 5.42 (9) and 10.61 (18)°, respectively. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are connected by inter-molecular N-H⋯O and C-H⋯S hydrogen bonds, forming R(2) (2)(12) ring motifs. In addition, there is a π-π stacking inter-action [centroid-centroid distance = 3.5188 (11) Å] between the pyrazole and benzene rings. These inter-actions link the mol-ecules into infinite chains along [001].

7-(4-Chloro-benzyl-idene)-3-[(4-chloro-phen-oxy)meth-yl]-6-(4-nitro-thio-phen-2-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazine.

In the title compound, C(22)H(13)Cl(2)N(5)O(3)S(2), the thia-diazine ring adopts a half-chair conformation. The benzene rings of the chloro-phen-oxy and chloro-benzyl groups and the thio-phene ring form dihedral angles of 35.6 (1), 80.7 (1) and 14.2 (1)°, respectively, with the triazole ring. In the crystal, mol-ecules are connected into sheets parallel to ([Formula: see text]11) by inter-molecular C-H⋯N and C-H⋯Cl hydrogen bonds. In addition, π-π stacking inter-actions are observed between thio-phene and triazole rings, and between inversion-related triazole rings [centroid-centroid distances = 3.5975 (11) and 3.4324 (11) Å].

7-Chloro-3-phenyl-benzo[4,5]thia-zolo[2,3-c][1,2,4]triazole.

In the title compound, C(14)H(8)ClN(3)S, the dihedral angle between the approximately planar triple-fused ring system (r.m.s. deviation = 0.065 Å) and the pendant phenyl ring is 62.25 (5)°. In the crystal, mol-ecules are linked into infinite chains along the c-axis direction by C-H⋯N hydrogen bonds. Aromatic π-π stacking inter-actions [centroid-centroid distances = 3.7499 (8) and 3.5644 (8) Å] and weak C-H⋯π inter-actions are also observed.

(E)-1-(3,4-Dimeth-oxy-phen-yl)-3-[4-(methyl-sulfan-yl)phen-yl]prop-2-en-1-one.

In the title compound, C(18)H(18)O(3)S, the C=C double bond exists in an E configuration and the dihedral angle between the two benzene rings is 11.74 (8)°. In the crystal, mol-ecules are linked into a three-dimensional network by C-H⋯O hydrogen bonds. The crystal structure is also stabilized by weak C-H⋯π inter-actions.

Ethyl 2-[2-(3-meth-oxy-phen-yl)hydrazinyl-idene]-3-oxobutano-ate.

The title compound, C(13)H(16)N(2)O(4), is approximately planar (r.m.s. deviation = 0.065 Šfor the 19 non-H atoms). An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif and the mol-ecule adopts an E conformation with respect to the central C=N double bond. In the crystal, pairs of inter-molecular C-H⋯O hydrogen bonds link adjacent mol-ecules into inversion dimers. The crystal structure also features weak C-H⋯π inter-actions.

4-(3-Chloro-phen-yl)-3-[(2,6-difluoro-benz-yl)sulfan-yl]-5-(3,4,5-trimeth-oxy-phen-yl)-4H-1,2,4-triazole.

In the title compound, C(24)H(20)ClF(2)N(3)O(3)S, the essentially planar triazole ring (r.m.s. deviation = 0.001 Å) forms dihedral angles of 22.35 (10), 68.17 (10) and 42.01 (10)° with the mean planes of the trimeth-oxy-phenyl, chloro-phenyl and difluoro-phenyl rings, respectively. A weak intra-molecular C-H⋯π inter-action occurs. In the crystal, mol-ecules are linked into sheets lying parallel to the bc plane by C-H⋯O and C-H⋯N hydrogen bonds. The crystal packing also features weak C-H⋯π inter-actions.

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

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.