1-(2-Hy­droxy­eth­yl)-3-phenyl­thio­urea

The title compound, C₉H₁₂N₂OS, was obtained unexpectedly in a multicomponent reaction of an equimolar ratio of phenyl isothio­cyanate, malononitrile and amino­ethanol. The –C(H₂)–N(H)–(C=S)–N(H)– methyl­thio­urea–methane group is almost normal to the phenyl ring, with a dihedral angle of 71.13 (9)°. The N—C—C—O torsion angle is 72.8 (2)°. In the crystal, mol­ecules are connected by N—H...O, O—H...S and N—H...O hydrogen bonds, forming a three-dimensional network.

2-Amino-4-(4-chloro­phen­yl)-5-oxo-5,6,7,8-tetra­hydro-4H-chromene-3-carbonitrile

In the title moleclue, C₁₆H₁₃ClN₂O₂, the cyclo­hexene ring is in a sofa conformation. The pyran ring is essentialy planar [maximum deviation = 0.038 (2) Å] and forms a dihedral angle of 89.68 (10)° with the benzene ring. In the crystal, mol­ecules are linked by pairs of N—H...N hydrogen bonds, forming inversion dimers with R₂²(12) ring motifs. These dimers are further linked by N—H...O hydrogen bonds into chains along [110]. Weak C—H...O hydrogen bonds are also present.

2-((E)-{[4-(Hy­droxy­meth­yl)phen­yl]imino}­meth­yl)phenol

The title compound, C₁₄H₁₃NO₂, adopts the enol–imine tautomeric form, with an intra­molecular O—H...N hydrogen bond which generates an S(6) ring motif. The dihedral angle between the aromatic rings is 7.85 (7)°. The crystal structure is stabilized by O—H...O, O—H...N and C—H...O hydrogen bonds, forming a two-dimensional array that stacks along the a axis. In addition, a C—H...π inter­action contributes to the stabilization of the crystal packing.

7-Bromo-9-(2-hy­droxy-4,4-dimethyl-6-oxocyclo­hex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetra­hydro-1H-xanthen-1-one

In the xanthene ring system of the title compound, C₂₃H₂₅BrO₄, the 4H-pyran ring is almost planar [maximum deviation = 0.040 (3) Å] and the cyclo­hexene ring adopts a sofa conformation. The cyclo­hexene ring attached to the xanthene system is puckered [Q_T = 0.427 (3) Å, θ = 55.0 (4) ° and φ = 164.4 (6) °]. In the crystal, mol­ecules are linked to each other by O—H...O and C—H...O hydrogen bonds.

2-Anilino-3-(2-hy­droxy­prop­yl)-4-methyl-1,3-thia­zol-3-ium chloride

In the title compound, C₁₃H₁₇N₂OS⁺·Cl⁻, the thia­zolium ring mean plane makes a dihedral angle of 55.46 (9)° with the benzene ring. In the propanol group, the N—C—C—C and N—C—C—O torsion angles are 172.58 (15) and 52.9 (2)°, respectively, and the S—C—C—C torsion angle is 178.99 (18)°. In the crystal, mol­ecules are linked by O—H...Cl and N—H...Cl hydrogen bonds, forming zigzag chains along [001]. There is also a C—H...Cl inter­action present.

2,2′-[(E,E)-cis-(Cyclo­hexane-1,4-di­yl)bis­(nitrilo­methanylyl­idene)]diphenol

In the title compound, C₂₀H₂₂N₂O₂, the asymmetric unit contains two independent half-mol­ecules, which are both completed by crystallographic inversion symmetry. The cyclo­hexane rings of both mol­ecules adopt chair conformations; the N atoms are in equatorial orientations in one mol­ecule and in axial orientations in the other. Both mol­ecules feature two intra­molecular O—H...N hydrogen bonds, which generate S(6) rings.

2-Amino-4-(4-chloro­phen­yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetra­hydro-4H-chromene-3-carbonitrile propan-2-one monosolvate

In the title compound, C₁₈H₁₇ClN₂O₂·C₃H₆O, the 4H-pyran ring is nearly planar [maximum deviation = −0.108 (1) Å] and the cyclo­hexene ring is puckered [puckering parameters Q_T = 0.4596 (17) Å, θ = 55.9 (2)° and φ = 226.5 (3)°]. The 4H-pyran ring is approximately perpendicular to the benzene ring [dihedral angle = 84.35 (7)°] and is almost coplanar with the mean plane of the cyclo­hexene ring [dihedral angle = 8.64 (7)°]. In the crystal, inversion-related main mol­ecules are linked into dimers by pairs of N—H...N hydrogen bonds, generating an R₂²(12) graph-set motif. These dimers are further connected by N—H...O and C—H...N hydrogen bonds, forming a layer structure extending parallel to the (011) plane. In addition, the mol­ecules within the layers inter­act with each other via C—H...π inter­actions.

N′-[(E)-4-(Dimethyl­amino)­benz­ylidene]-2-(5-meth­oxy-2-methyl-1H-indol-3-yl)acetohydrazide

In the title compound, C₂₁H₂₄N₄O₂, inversion-related mol­ecules are linked into dimers through pairs of N—H...O hydrogen bonds, which generate R₂²(8) motifs. As well as dimer formation, an additional N—H...O hydrogen bond and two C—H...π contacts, involving H atoms from the phenyl ring and the pyrrole and benzene rings of the indole system, generate a three-dimensional network.

5-(4-Methyl­phen­yl)-3-phenyl­cyclo­hex-2-en-1-one

In the title compound, C₁₉H₁₈O, the cyclo­hexene ring has an envelope conformation with the methine C atom on the flap. The phenyl and methyl­phenyl rings form a dihedral angle of 85.93 (11)°. The crystal packing is consolidated by van der Waals forces and weak C—H...π inter­actions.

2-Amino-4-(4-meth­oxy­phen­yl)-5-oxo-5,6,7,8-tetra­hydro-4H-chromene-3-carbonitrile 1,4-dioxane hemisolvate

In the crystal structure of the title compound, C₁₇H₁₆N₂O₃·0.5C₄H₈O₂, pairs of N—H...N hydrogen bonds link mol­ecules into dimers with R₂²(12) motifs, which are connected by N—H...O hydrogen bonds, forming a supra­molecular array in the ab plane. The 1,4-dioxane ring, which lies about an inversion center, adopts a chair conformation.

2-Amino-4-(4-meth­oxy­phen­yl)-7,7-di­methyl-5-oxo-5,6,7,8-tetra­hydro-4H-chromene-3-carbonitrile propan-2-one monosolvate

In the crystal structure of the title compound, C₁₉H₂₀N₂O₃·C₃H₆O, mol­ecules are linked into inversion dimers with an R₂²(12) motif by pairs of N—H...N hydrogen bonds. These dimers are further connected into chains running along the a axis by N—H...O hydrogen bonds. C—H...N and C—H...π inter­actions also feature in the packing. The cyclohexene ring adopts nearly an envelope conformation [puckering parameters are Q_T = 0.456 (2) Å, θ = 54.6 (3)° and φ = 225.2 (3)°].

2-Amino-4-(4-methyl­phen­yl)-5-oxo-5,6,7,8-tetra­hydro-4H-chromene-3-carbonitrile

The 4H-pyran ring of the title compound, C₁₇H₁₆N₂O₂, is nearly planar [maximum deviation = 0.077 (2) Å] and the cyclo­hexene ring adopts a flattened chair conformation [puckering parameters: Q_T = 0.435 (2) Å, θ = 122.0 (3)° and φ = 53.5 (3)°]. The 4H-pyran ring is almost perpendicular to the benzene ring [dihedral angle = 87.23 (8)°] and is almost coplanar with the mean plane of the cyclo­hexene ring [dihedral angle = 8.01 (8)°]. In the crystal, inversion-related mol­ecules are linked by pairs of inter­molecular N—H...N hydrogen bonds, forming inversion dimers with R₂²(12) ring motifs. These dimers are further connected by N—H...O and C—H...N hydrogen bonds, forming a layer structure extending parallel to (0-12). Mol­ecules within the layers inter­act with each other via C—H...π inter­actions.

(E)-N′-(5-Bromo-2-hy­droxy­benzyl­idene)-2-(4-isobutyl­phen­yl)propano­hydrazide

The title compound, C₂₀H₂₃BrN₂O₂, containing an ibuprofen core, crystallizes with three independent mol­ecules of similar conformation in the asymmetric unit. In these three mol­ecules, the two benzene rings make dihedral angles of 82.7 (2), 71.2 (2) and 78.0 (3)° with respect to each other. The atoms of the isobutyl groups in two of the mol­ecules are disordered over two positions, with site-occupancy ratios of 0.516 (8):0.484 (8) and 0.580 (8):0.420 (8). In the crystal, mol­ecules are linked by N—H...O, C—H...O and O—H...N hydrogen bonds. Furthermore, C—H...π inter­actions are also observed.

(Z)-3-(2-Hy­droxy­eth­yl)-2-(phenyl­imino)-1,3-thia­zolidin-4-one

In the title compound, C₁₁H₁₂N₂O₂S, the thia­zole and phenyl rings are inclined at 56.99 (6)° to one another. The thia­zole ring is planar with an r.m.s. deviation for the five ring atoms of 0.0274 Å. The presence of the phenyl­imine substituent is confirmed with the C=N distance to the thia­zole ring of 1.2638 (19) Å. The mol­ecule adopts a Z conformation with respect to this bond. The –OH group of the hy­droxy­ethyl substituent is disordered over two positions with relative occupancies 0.517 (4) and 0.483 (4). In the crystal, O—H...O hydrogen bonds, augmented by C—H...N contacts, form dimers with R₂²(11) rings and generate chains along the b axis. Parallel chains are linked in an obverse fashion by weak C—H...S hydrogen bonds. C—H...O hydrogen bonds together with C—H...π contacts further consolidate the structure, stacking mol­ecules along the b axis.

2-(1,3-Dioxoisoindolin-2-yl)acetic acid–N′-[(E)-2-meth­oxy­benzyl­idene]pyridine-4-carbohydrazide (1/1)

In the title 1:1 cocrystal, C₁₀H₇NO₄·C₁₄H₁₃N₃O₂, mol­ecules are linked by inter­molecular C—H...O, N—H...O and O—H...N hydrogen bonds, forming a three-dimensional network. In addition, π–π stacking inter­actions [with centroid–centroid distances of 3.5723 (19) and 3.6158 (18) Å] are observed.

2-Eth­oxy-4-(4-methyl­phen­yl)-6-phenyl­pyridine-3-carbonitrile

The title compound, C₂₁H₁₈N₂O, crystallized with two independent mol­ecules (A and B) in the asymmetric unit. In mol­ecule A, the central pyridine ring forms dihedral angles of 14.55 (13) and 39.14 (12)° with the terminal phenyl and benzene rings, respectively. The latter rings make a dihedral angle of 33.06 (13)° with each other. The corresponding values for mol­ecule B are 26.86 (13), 41.82 (12) and 38.99 (13)°, respectively. In the crystal, the B mol­ecules are linked via a pair of weak C—H...N hydrogen bonds, forming inversion dimers. In addition, C—H...π inter­actions and π–π [centroid–centroid distances = 3.5056 (16) and 3.8569 (17) Å] stacking inter­actions are observed.

2-Anilino-5,7-dimethyl­pyrazolo­[1,5-a]pyrimidine-3-carbonitrile

The title compound, C₁₅H₁₃N₅, crystallizes with two independent mol­ecules in the asymmetric unit. The mol­ecular conformations are stabilized by C—H...N contacts forming S(6) ring motifs. In the crystal, pairs of mol­ecules are connected into R₂²(12) dimers by N—H...N hydrogen bonds. C—H...π inter­actions and π–π stacking inter­actions [centroid–centroid distances = 3.6085 (8), 3.6657 (8), 3.4745 (8) and 3.5059 (8) Å] also also observed.

5-Amino-3-anilino-1H-pyrazole-4-carbonitrile

In the title compound, C₁₀H₉N₅, the phenyl ring is twisted with respect to the pyrazole ring, forming a dihedral angle of 24.00 (6)°. In the crystal, mol­ecules are linked by N—H...N hydrogen bonds into chains running parallel to [010] containing alternating R₂²(6) and R₂²(12) rings. Further inter­actions are found in the crystal, viz. N—H...π(phen­yl) inter­actions and weak face-to-face π–π stacking inter­actions [centroid–centroid distance = 3.8890 (6) Å] between the centroids of the pyrazole and phenyl rings are observed.

4-[(2E)-2-(2-Hy­droxy­benzyl­idene)hydrazin-1-yl]benzonitrile

The asymmetric unit of the title Schiff base, C₁₄H₁₁N₃O, contains two independent mol­ecules which have similar conformations. The dihedral angles between the benzene rings are 4.19 (9) and 14.18 (9)° in the two mol­ecules. An intra­molecular O—H...N hydrogen bond stabilizes the mol­ecular conformation of each mol­ecules. The crystal packing is dominated by pairs of equivalent N—H...N and C—H...O hydrogen bonds which arrange the mol­ecules into layers parallel to (-111).

2-[(Phenyl­carbamo­yl)amino]­butyl N-phenyl­carbamate

In the title compound, C₁₈H₂₁N₃O₃, the terminal phenyl rings make a dihedral angle of 86.3 (5)°. In the crystal, mol­ecules are linked by N—H...O hydrogen bonds into chains along [001], forming parallel C(4) and R₁²(6) graph-set motifs.

2-(3,4-Dimeth­oxy­phen­yl)-4,5-diphenyl-1-(prop-2-en-1-yl)-1H-imidazole

In the title compound, C₂₆H₂₄N₂O₂, the planar 1H-imidazole ring makes dihedral angles of 35.78 (4), 26.35 (5) and 69.75 (5)°, respectively, with the dimeth­oxy­phenyl ring and the phenyl rings in the 4- and 5-positions. In the crystal, C—H...O hydrogen bonds connect neighbouring mol­ecules, forming infinite chains running along the b axis. Furthermore, the crystal structure exhibits a C—H-...π inter­action between a methyl H atom and a phenyl ring from an adjacent mol­ecule.

2-(4-Meth­oxy­phen­yl)-4,5-diphenyl-1-(prop-2-en-1-yl)-1H-imidazole

The asymmetric unit of the title compound, C₂₅H₂₂N₂O, contains two independent mol­ecules (A and B), with significantly different conformations. In mol­ecule A, the central imidazole ring makes dihedral angles of 88.26 (10) and 12.74 (11)° with the two phenyl rings, and 22.06 (9)° with the benzene ring. In mol­ecule B, one of the phenyl rings is disordered over two sites, each having an occupancy of 0.5. Here the central imidazole ring forms dihedral angles of 79.24 (10)° with the ordered phenyl ring, and 3.5 (5) and 22.6 (5)° with the two parts of the disordered phenyl ring. The dihedral angle involving the benzene ring is 67.49 (10)°. The —N—C(H₂)—C(H)—C(H₂) torsion angles of the prop-1-ene group in the two mol­ecules are very similar, 0.5 (3) and 1.3 (4)° for mol­ecules A and B, respectively. The crystal structure is stabilized by C—H...π inter­actions.

4-Bromo-2-[(E)-{[4-nitro-2-(trifluoro­meth­yl)phen­yl]imino}­meth­yl]phenol

Except two F atoms of the –CF₃ group, the title compound, C₁₄H₈BrF₃N₂O₃, has an almost planar conformation, the dihedral angle between the aromatic rings being 3.60 (16)°. The mol­ecule adopts the enol–imine tautomeric form, with an intra­molecular O—H...N hydrogen bond, which generates an S(6) ring motif. In the crystal, face-to-face π–π stacking [centroid–centroid distances = 3.669 (2) and 3.732 (2) Å] between the aromatic rings of the mol­ecules, which lie in sheets parallel to (202), help to establish the packing.

4-Phenyl-1H-1,5-benzodiazepin-2(3H)-one

In the title compound, C₁₅H₁₂N₂O, the phenyl ring makes a dihedral angle of 32.45 (9)° with the benzene ring of the 1,5-benzodiazepin-2-one unit. The seven-membered ring adopts a boat conformation with the methyl­ene group as the prow and the fused benzene-ring C atoms as the stern. In the crystal, inversion dimers linked by pairs of N—H...O hydrogen bonds generate R₂²(8) loops. The dimers are further linked by C—H...O hydrogen bonds, so forming a column along the a-axis direction.

Dibenzo[b,g]indeno­[1′,2′:3,4]fluoreno[1,2-d]oxonine-5,11,16,21-tetra­one

The asymmetric unit of the title compound, C₃₄H₁₆O₅, contains two independent mol­ecules (A and B) with similar conformations. The two benzene rings attached to the nine-membered ring are inclined to one another at 63.62 (14)° in mol­ecule A and 68.23 (12)° in mol­ecule B. One intra­moleculer C—H...O hydrogen bond occurs in mol­ecule A and two are observed in mol­ecule B. In the crystal, mol­ecules are linked by weak C—H...O hydrogen bonds, forming a three-dimensional network structure with R²₂(10) and R²₂(24) ring motifs. Aromatic π–π stacking interactions [centroid–centroid distances = 3.7572 (19), 3.6996 (19) and 3.7043 (19) Å] are also observed. The unit cell contains a pair of voids of 37 (2) ų about an inversion centre but the residual electron density (highest peak = 0.19 e Å⁻³ and deepest hole = −0.20 e Å⁻³) in the difference Fourier map suggests that no solvent mol­ecule occupies this void.