2-[1-(2-Hy­droxy-6-meth­oxy­phen­yl)ethyl­idene]-N-methyl­hydrazinecarbothio­amide acetonitrile monosolvate

In the title compound, C₁₁H₁₅N₃O₂S·C₂H₃N, the dihedral angle between the benzene ring and the mean plane of the hydrazinecarbothio­amide group is 75.1 (2)°. In the crystal, the main mol­ecule is linked to the solvent mol­ecule by a weak N—H...N hydrogen bond while O—H...S hydrogen bonds link the mol­ecules into columns along [100].

Bosentan monohydrate

In the title compound, C₂₇H₂₉N₅O₆S·H₂O {systematic name: 4-tert-butyl-N-[6-(2-hy­droxy­eth­oxy)-5-(2-meth­oxy­phen­oxy)-2-(pyrimidin-2-yl)pyrimidin-4-yl]benzene-1-sulfonamide monohydrate], the dihedral angle between the mean planes of the pyrimidine rings is 27.0 (1)°. The dihedral angle between the mean planes of the benzene rings is 47.7 (8)°, forming a U-shaped channel around the chain of twisted pyrimidine rings. The crystal packing is stabilized by O—H...O, O—H...N and N—H...O hydrogen bonds with a single water mol­ecule, and weak O—H...N inter­molecular inter­actions between the hy­droxy group and one of the pyrimidine rings producing an two-dimensional supra­molecular array in the bc plane. The title compound studied was a merohedral twin with the major component being approximately 57%.

6-(3-Chloro­phen­yl)imidazo[2,1-b][1,3,4]thia­diazole

In the title compound, C₁₀H₈ClN₃S, the dihedral angle between the mean planes of the benzene and imidazo[2,1-b][1,3,4]thia­diazole rings is 6.0 (9)°. In the crystal, mol­ecules are assembled by the formation of centrosymmetric dimers by π-stacking of the thia­diazole and benzene rings of neighboring mol­ecules [centroid–centroid distance = 3.6938 (11) Å] along [010].

Diphenyl­methyl benzoate

In the title mol­ecule, C₂₀H₁₆O₂, the dihedral angle between the phenyl rings of the diphenyl­methyl group is 68.3 (2)°. The benzoate group is essentially planar, with a maximum deviation of 0.017 (2) Å for the carbonyl O atom, and the two phenyl rings are twisted by 27.5 (4) and 85.6 (9)° from this plane. In the crystal, weak C—H...O hydrogen bonds link mol­ecules along [100].

Cinnarizinium fumarate

In the title salt {systematic name: 4-diphenyl­methyl-1-[(E)-3-phenyl­prop-2-en-1-yl]piperazin-1-ium (2Z)-3-carb­oxy­prop-2-enoate}, C₂₆H₂₉N₂⁺·C₄H₃O₄⁻, the piperazine ring in the cation adopts a distorted chair conformation and contains a positively charged N atom with quaternary character. The dihedral angle between the mean planes of the phenyl rings of the diphenyl­methyl group is 74.2 (7)° and those between these rings and the phenyl ring of the 3-phenyl­prop-2-en-1-yl group are 12.7 (9) and 80.6 (8)°. In the crystal, N—H...O and O—H...O hydrogen bonds form chains along [001]. Weak C—H...O inter­actions connect parallel chains along [010], forming layers perpendicular to the a-axis direction.

Olanzapinium dipicrate

The asymmetric unit of the title salt [systematic name: 2-methyl-4-(4-methyl­piperazin-4-ium-1-yl)-10H-thieno[2,3-b][1,5]benzodiazepinium bis­(2,4,6-trinitro­phenolate)], C₁₇H₂₂N₄S²⁺·2C₆H₂N₃O₇⁻, consists of a diprotonated olanzapinium cation and two independent picrate anions. In the cation, the piperazine ring adopts a distorted chair conformation and contains a positively charged N atom with quaternary character and the N atom in the seven-membered 1,5-diazepine ring, which adopts a boat configuration, is also protonated. The dihedral angle between the benzene and thiene rings flanking the diazepine ring is 58.8 (1)°. In one of the picrate anions, a nitro group is disordered over two sets of sites in a 0.748 (5):0.252 (5) ratio, and the benzene ring has a flat envelope conformation with the O⁻ C atom displaced from the mean plane of the other five C atoms [maximum deviation 0.0151 (14) Å] by 0.1449 (14) Å. In the crystal, N—H...O hydrogen bonds and weak inter­molecular C—H...S and C—H...O inter­actions link the components, forming a three-dimensional network.

Orphenadrinium dihydrogen citrate

In the title salt, C₁₈H₂₄NO⁺·C₆H₇O₇⁻, the dihedral angle between the benzene rings in the cation is 74.2 (5)°. In the crystal, anion–anion O—H...O hydrogen bonds and weak O—H...O inter­actions form infinite chains along [100]. Between these chains, cation–anion N—H—O hydrogen bonds are observed, forming an alternate pattern of cation and anion layers and leading to a two-dimensional network parallel to (100).

Ethyl 6-(6-meth­oxy­naphthalen-2-yl)-4-(naphthalen-2-yl)-2-oxocyclo­hex-3-ene-1-carboxyl­ate

The title compound, C₃₀H₂₆O₄, contains an oxo-cyclo­hexane ring in a distorted half-chair configuration, with disorder of two C atoms in a 0.859 (4):0.141 (4) ratio. The dihedral angle between the mean planes of the two napthalene ring systems is 58.6 (8)°.

(E)-N'-(4-Fluoro­benzyl­idene)-2-(3-methyl­phen­yl)acetohydrazide

In the title compound, C₁₆H₁₅FN₂O, the dihedral angles between the benzene rings are74.7(8), 74.1 (1), 74.2 (7) and 74.3 (5)° in the four independent mol­ecules in the asymmetric unit. In the crystal, N-H-O hydrogen bonds involving the hydrazide and acetyl groups, which form R₂²(18) ring motifs, link the mol­ecules into dimers, which form columns along [010].

N-(4-Bromo­phen­yl)acetamide: a new polymorph

A new polymorph of the title compound, C₈H₈BrNO, has been determined at 173 K in the space group P2₁/c. The previous room-temperature structure was reported to crystallize in the ortho­rhom­bic space group Pna2₁ [Andreetti et al. (1968). Acta Cryst. B24, 1195–1198]. In the crystal, mol­ecules are linked by N—H...O hydrogen bonds forming chains along [010]. Weak C—H...π inter­actions are also present.

Cinnarizinium bis­(p-toluene­sulfonate) dihydrate

The asymmetric unit of the title salt [systematic name: 1-benzhydryl-4-cinnamylpiperazine-1,4-diium bis­(p-toluene­sulfonate) dihydrate], C₂₆H₃₀N₂²⁺·2C₇H₇O₃S⁻·2H₂O, consists of a diprotonated cinnarizinium cation hydrogen bonded through two water mol­ecules to two independent p-toluene­sulfonate anions, one which is disordered over two sets of sites in a 0.793 (3):0.207 (3) ratio. In the cation, the piperazine ring adopts a chair configuration and contains two positively charged N atoms with quarternery character. The dihedral angle between the two benzene rings in the benzhydr­yl group is 71.8 (1)°. The benzene ring flanked opposite the piperazine ring is twisted by 75.9 (9) and 8.8 (3)° from these two benzene rings. In the crystal, the [N—H...O_water—H...O([pdbond]S)]₂ hydrogen-bonded asymmetric unit is connected by further O—H...O hydrogen bonds linking the components into chains along [100].

2-(2,6-Dichloro­phen­yl)-N-(1,3-thia­zol-2-yl)acetamide

In the title compound, C₁₁H₈Cl₂N₂OS, the mean plane of the dichloro­phenyl ring is twisted by 79.7 (7)° from that of the thia­zole ring. In the crystal, molecules are linked via pairs of N—H...N hydrogen bonds, forming inversion dimers which stack along the a-axis direction.

{2-[1-(2-Meth­oxy-6-oxidophenyl-κO⁶)ethyl­idene]-N-methyl­hydrazinecarbo­thio­amidato-κ²N²,S}(tri­phenyl­phosphane-κP)palladium(II) ethanol monosolvate

In the title compound, [Pd(C₁₁H₁₃N₃O₂S)(C₁₈H₁₅P)]·C₂H₅OH, the Pd^II atom is tetra­coordinated in a slightly distorted square-planar environment by three donor atoms (NOS) from a thio­semicarbazonate ligand, forming five- and six-membered chelate rings, and a P atom from a neutral tri­phenyl­phosphane group. The five-membered ring adopts a distorted envelope conformation with Pd^II as the flap atom, while the six-membered ring forms a slightly twisted screw-boat conformation. A slightly distorted screw-boat form of a meth­oxy­phenyl group is fused to the six-membered ring. Weak C—H...O inter­actions form dimers in the asymmetric unit and along [001] which help to stabilize the crystal packing.

(Z)-4-[2-(2,4-Dimethyl­phen­yl)hydrazinyl­idene]-3-methyl­pyrazol-5(1H)-one

The mol­ecule of the title compound, C₁₂H₁₄N₄O, is roughly planar, with a dihedral angle of 8.0 (8)° between the benzene and pyrazole rings, and an intra­molecular N—H...O hydrogen bond forms an S(6) ring motif. In the crystal, mol­ecules are linked into an inversion dimer by a pair of N—H...O hydrogen bonds, which form an R₂²(8) ring motif.

Amicarbazone

Three independent mol­ecules comprise the asymmetric unit of the title compound, C₁₀H₁₉N₅O₂, (systematic name: 4-amino-N-tert-butyl-3-isopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazole-1-carboxamide) . In all three mol­ecules, the triazole ring and the carboxamide group are almost coplanar [within 4.0–5.9 (9)°], particularly because of the formation of an intra­molecular N—H...O hydrogen bond. On other hand, the orientation of the isopropyl group varies significantly from mol­ecule to mol­ecule. The crystal packing is dominated by N—H...O and N—H...N hydrogen bonds, which connect the mol­ecules into infinite chains along [010].

2-(3,4-Dichloro­phen­yl)-N-(1,3-thia­zol-2-yl)acetamide

In the title compound, C₁₁H₈Cl₂N₂OS, the mean plane of the dichloro­phenyl ring is twisted by 61.8 (1)° from that of the thia­zole ring. In the crystal, mol­ecules are linked via pairs of N—H...N hydrogen bonds with an R₂²(8) graph-set motif, forming inversion dimers which stack along the a-axis direction.

2-(2,4-Di­chloro­phen­yl)-N-(1,3-thia­zol-2-yl)acetamide

In the title compound, C₁₁H₈Cl₂N₂OS, the mean plane of the di­chloro­phenyl ring is twisted by 72.4 (1)° from that of the thia­zole ring. In the crystal, mol­ecules are linked via pairs of N—H...N hydrogen bonds with an R₂²(8) graph-set motif and weak C—H...O inter­actions, forming inversion dimers which stack along the c-axis direction.

Methyl 2-{2-[(2-methyl­phen­oxy)meth­yl]phen­yl}-2-oxoacetate

In the title compound, C₁₇H₁₆O₄, the dihedral angle between the benzene rings is 4.4 (2)°. In the crystal, weak C—H...O hydrogen bonds connect mol­ecules along [001].

4-Hy­droxy-N-methyl­benzamide

Three independent mol­ecules comprise the asymmetric unit of the title compound, C₈H₉NO₂, in which the dihedral angles between the amide group and the benzene ring are 3.0 (2), 4.0 (3) and 3.3 (9)°. In the crystal, O—H...O hydrogen bonds and weak C—H...N inter­actions are observed, forming infinite chains along [101].

(2E)-1-(4-Chloro­phen­yl)-3-(4-nitro­phen­yl)prop-2-en-1-one

In the title compound, C₁₅H₁₀ClNO₃, a substituted chalcone, the dihedral angle between the benzene rings is 5.1 (7)°. The nitro group makes a dihedral angle of 12.5 (3)° with the benzene ring to which it is attached. In the crystal, weak C—H...O inter­actions link the mol­ecules into a one-dimensional array along [010]. The crystal studied was an inversion twin, with a refined ratio for the twin components of 0.6060 (9):0.3939 (1).

2-(4-Bromo­phen­yl)-N-(pyrazin-2-yl)acetamide

In the title compound, C₁₂H₁₀BrN₃O, the dihedral angle between the mean planes of the 4-bromo­phenyl and pyrazin-2-yl rings is 54.6 (3)°. An intra­molecular C—H...O hydrogen bond generates an S(6) graph-set motif. In the crystal, weak N—H...N hydrogen bonds link the mol­ecules into chains along [100]. The chains are linked via C—H...N and C—H...O hydrogen bonds, forming two-dimensional networks lying parallel to the ab plane.

2-(4-Bromo­phen­yl)-N-(3,4-di­fluoro­phen­yl)acetamide

In the title compound, C₁₄H₁₀BrF₂NO, the dihedral angle between the mean planes of the 4-bromo­phenyl and 3,4-di­fluoro­phenyl rings is 66.4 (1)°. These two planes are twisted by 40.0 (5) and 86.3 (2)°, respectively, from that of the acetamide group. In the crystal, N—H...O hydrogen bonds and weak C—H...O and C—H...F inter­actions form infinite chains along [100].

Rupatadine

In the title compound (systematic name: 8-chloro-11-{1-[(5-methyl­pyridin-3-yl)meth­yl]piperidin-4-yl­idene}-6,11-di­hydro-5H-benzo[5,6]cyclo­hepta­[1,2-b]pyridine), C₂₆H₂₆ClN₃, the dihedral angle between the mean planes of the chloro­phenyl and cyclo­hepta­[1,2-b]pyridinyl rings fused to the cyclo­heptane ring is 56.6 (1)°. The mean planes of the cyclo­hepta­[1,2-b]pyridinyl and 5-methyl­pyridin-3-yl rings are twisted by 64.9 (4)°. The central piperizene group is in a slightly distorted chair configuration. A weak intra­molecular C—H...N inter­action is observed between the cyclo­hepta­[1,2-b]pyridinyl and piperidin-4-yl­idene moieties.

2-(4-Chloro­phen­yl)-N-(3,4-di­fluoro­phen­yl)acetamide

In the title compound, C₁₄H₁₀ClF₂NO, the dihedral angle between the mean planes of the 4-chloro­phenyl and 3,4-di­fluoro­phenyl rings is 65.2 (1)°. These two planes are twisted by 83.5 (5) and 38.9 (9)°, respectively, from that of the acetamide group. In the crystal, N—H...O hydrogen bonds form infinite chains along [100]. Weak C—H...O and C—H...F inter­actions are also observed and stack mol­ecules along the b axis.

Bruceolline D: 3,3-dimethyl-1H,4H-cyclo­penta­[b]indol-2(3H)-one

The title compound, C₁₃H₁₃NO, crystallizes with four independent mol­ecules in the asymmetric unit. The 12-membered penta­[b]indole rings are essentially planar, with maximum deviations ranging from 0.034 (4) to 0.036 (4) Å in the four unique mol­ecules. In the crystal, weak C—H...O inter­actions are observed, which link the mol­ecules into chains along [010].

(2S*,5R*)-2,5-Dimethyl-1,4-bis­(pyridin-2-ylmeth­yl)piperazine

The title compound, C₁₈H₂₄N₄, resides on a crystallographic inversion centre, so that the asymmetric unit comprises one half-mol­ecule. The piperazine ring adopts a chair conformation, with the mean planes of the two equatorial pyridine rings parallel to each other and separated by 2.54 (3) Å. No classical hydrogen bonds are observed.

2-[(2-Chloro­phen­yl)(hy­droxy)meth­yl]phenol

In the title compound, C₁₃H₁₁ClO₂, the dihedral angle between the mean planes of the 2-chloro­phenyl and phenol rings is 87.4 (9)°. The methyl hy­droxy group lies nearly perpendicular to the plane of its attached benzene ring [O—C—C—C torsion angle = 84.3 (3)°]. The two hy­droxy groups lie on the same side of the mol­ecule and are in a slightly twisted gauche conformation [O—C—C—O torsion angle = 77.1 (8)°] to each other. In the crystal, O—H...O hydrogen bonds between nearby methyl­hydroxy groups form dimers in alternating pairs aligned diagonally along the b axis. A view along the c axis reveals a hexa­meric aggregate mediated by a ring of six O—H...O hydrogen bonds generating an R₆⁶(12) motif loop.

Carbinoxaminium dipicrate

In the dication of the title salt, C₁₆H₂₁ClN₂O²⁺·2C₆H₂N₃O₇⁻ [systematic name: 2-{(4-chloro­phen­yl)[2-(di­methyl­aza­nium­yl)eth­oxy]meth­yl}pyridinium bis­(2,4,6-tri­nitro­phenolate), contains a carbinoxaminium dication and two picrate anions, which are held together through inter­molecular N—H...O hydrogen bonds. In the dication, the two aromatic rings form a dihedral angle of 80.1 (1)°. In the two independent picrate anions, the nitro groups are twisted from the benzene plane, the largest dihedral angle in each ion being 42.8 (1) and 81.1 (5)°. In the crystal, in addition to the classical N—H...O hydrogen bonds, weak C—H...O hydrogen bonds and π–π inter­actions between the aromatic rings of the anions [centroid–centroid distances of 3.5768 (15) and 3.7436 (15) Å] help to establish the packing.

2-[1-(2-Hy­droxy-4-meth­oxy­phen­yl)ethyl­idene]-N-methyl­hydrazinecarbo­thio­amide

In the title compound, C₁₁H₁₅N₃O₂S, the dihedral angle between the mean planes of the benzene ring and hydrazinecarbo­thio­amide group is 9.2 (1)°. An intra­molecular O—H...N hydrogen bond is observed, serving to maintain an approximately planar conformation for the molecule. In the crystal, inversion dimers linked by C—H...O inter­actions occur. Further C—H...O contacts link dimers into (010) chains.

Flunarizinium hydrogen maleate

In the cation of the title salt {systematic name: 4-[bis­(4-fluoro­phen­yl)meth­yl]-1-[(2E)-3-phenyl­prop-2-en-1-yl]piperazin-1-ium hydrogen maleate}, C₂₆H₂₇F₂N₂⁺·C₄H₃O₄⁻, the protonated piperazine ring is in a chair conformation. The dihedral angle between the 4-fluoro­phenyl rings is 68.2 (2)°. An intra­molecular O—H...O hydrogen bond occurs in the anion. In the crystal, N—H...O, C—H...O and C—H...F inter­actions are observed, which link the ions into [001] chains.

Bruceolline J: 2-hy­droxy-3,3-dimethyl-2,3-di­hydro­cyclo­penta­[b]indol-1(4H)-one

The 12-membered cyclo­penta­[b]indole ring system in the title compound, C₁₃H₁₃NO₂, deviates only slightly from planarity (r.m.s. deviation = 0.051 Å). In the crystal, N—H...O and O—H...O hydrogen bonds link the mol­ecules into sheets parallel to (100). The five-membered cyclopentanone ring is in slightly distorted envelope conformation with the C atom bearing the hydroxy substituent as the flap.

3-Amino-1H-pyrazol-2-ium tri­fluoro­acetate

The asymmetric unit of the title salt, C₃H₆N₃⁺·C₂F₃O₂⁻, contains two independent 3-amino­pyrazolium cations and two independent tri­fluoro­acetate anions. The F atoms of both anions were refined as disordered over two sets of sites, with common occupancy ratios of 0.639 (12):0.361 (12). In the crystal, the cations and anions are linked via N—H...O hydrogen bonds, forming chains along [100] and [010].

Ethyl 2-amino-6-(4-bromo­phen­yl)-4-(4-fluoro­phen­yl)cyclo­hexa-1,3-diene-1-carboxyl­ate

In the title compound, C₂₁H₁₉BrFNO₂, two independent mol­ecules crystallize in the asymmetric unit. The cyclo­hexa-1,3-diene ring is in a slightly distorted screw-boat conformation. The dihedral angles between the mean planes of the 4-bromo­phenyl and 4-fluoro­phenyl rings are 81.0 (3) and 76.4 (2)° in the two independent mol­ecules. In the crystal, N—H...O hydrogen bonds link the molecules into [100] chains.

Desvenlafaxinium chloranilate ethyl acetate solvate

In the cation of the title compound, C₁₆H₂₆NO₂⁺·C₆HCl₂O₄⁻·C₄H₈O₂, the 1-hy­droxy-cyclo­hexyl ring adopts a slightly distorted chair conformation. The dihedral angle between the mean planes of the 1-hy­droxy­cyclo­hexyl and 4-hy­droxy­phenyl rings is 84.0 (8)°. In the anion, the hydroxyl H atom is twisted slightly out of the ring plane with a C—C—O—H torsion angle of −171.9°. Disorder was modeled for the methyl group of the acetate group in the solvate with an occupancy ratio of 0.583 (15): 0.417 (15). In the crystal, O—H...O hydrogen bonds are observed between cations and between cations and anions, while bifuricated N—H...(O,O) cation–anion hydrogen bonds are also present, forming chains along [010] and [100]. In addition weak cation–anion and cation–solvate C—H...O inter­actions occur.

3-(1H-Imidazol-1-yl)propanaminium picrate

In the title salt [systematic name: 3-(1H-imidazol-1-yl)propanaminium 2,4,6-tri­nitro­phenolate], C₆H₁₂N₃⁺·C₆H₂N₃O₇⁻, there are five independent cation–anion pairs (A, B, C, D, E) in the asymmetric unit. In the cation, the ammonium group is protonated with the amino­propyl group nearly at right angles to the mean plane of the imidazole ring showing C—N—C—C torsion angles ranging from 79.6 (2) to 99.79 (19)° in the five cations. The nitro groups in the anion are twisted from the benzene mean plane with maximum dihedral angles subtended by nitro substituents ortho to the phenolate O atom of 26.0 (2) and 37.3 (7) (A), 28.9 (5) and 35.3 (1) (B), 34.7 (7) and 36.9 (7) (C), 14.7 (4) and 36.9 (2) (D) and 33.1 (1) and 35.4 (3)° (E). In contrast, the nitro groups in the para positions lie much closer to the aromatic ring plane, subtending dihedral angles of 1.8 (3) (A), 3.5 (3) (B), 6.03 (C), 2.1 (3) (D) and 7.7 (1)° (E). Disorder is observed for one O atom of an ortho nitro group in anion D with an occupancy ratio of 0.53 (5):0.47 (5). In the crystal, N—H...O cation–anion and N—H...N cation–cation hydrogen bonds are observed, linking the ions into chains along [010]. In addition, weak C—H...O cation–anion inter­actions occur.

N-(1,3-Benzo­thia­zol-2-yl)acetamide

The title compound, C₉H₈N₂OS, crystallizes with two mol­ecules (A and B) in the asymmetric unit. The dihedral angles between the mean planes of the 1,3-benzo­thia­zol-2-yl ring system and the acetamide group are 2.7 (4) (mol­ecule A) and 7.2 (2) Å (mol­ecule B). In the crystal, pairs of N—H...N hydrogen bonds link the A and B mol­ecules into dimers, generating R₂²(8) loops. The dimers stack along [100].

Bis{4-[(1,3-benzodioxol-5-yl)meth­yl]piperazin-1-yl}methane

In the title compound, C₂₅H₃₂N₄O₄, both piperazine rings adopt a chair conformation. One of dioxolane ring systems is essentially planar [dihedral angle = 0.9 (2)°] while the other adopts a slightly disordered envelope conformation, the mean plane of the dioxolane ring being twisted by 3.6 (2)° from that of the benzene ring. The dihedral angle between the benzene rings is 69.9 (5)°. No classical hydrogen bonds were observed.

Methyl 2-[4-(tri­fluoro­meth­yl)phenyl­sulfan­yl]benzoate

In the title compound, C₁₅H₁₃F₃O₂S, the dihedral angle between the benzene rings is 79.5 (1)°. The ester group is twisted by 7.6 (1)° from the mean plane of the adjacent benzene ring. Disorder was modeled over two sites for one F atom of the tri­fluoro­methyl group with an occupancy ratio of 0.54 (6):0.46 (6). In the crystal, mol­ecules are linked via weak C—H...O hydrogen bonds, forming two-dimensional networks lying parallel to (101). The networks are linked via C—H...π inter­actions, leading to the formation of a three-dimensional supra­molecular structure.

1-[4-(4-Hy­droxy­phen­yl)piperazin-1-yl]ethanone

In the title compound, C₁₂H₁₆N₂O₂, the piperazine ring has a chair conformation. The dihedral angle between the mean planes of the benzene ring and the acetyl group is 48.7 (1)°. In the crystal, mol­ecules are linked via O—H...O hydrogen bonds, forming chains propagating along [010].

4-Methyl-N-(4-nitro­benzyl­idene)piperazin-1-amine

In the title compound, C₁₂H₁₆N₄O₂, the piperazine ring is in a slightly distorted chair conformation. In the mol­ecule, the mean plane of the nitro group is twisted by 8.0 (3)° from that of the benzene ring. Also, the mean plane of the 2-nitro­benzyl ring is twisted slightly from that of the piperazine ring, with an N—N=C—C torsion angle of −176.24 (11)°. In the crystal, pairs of weak C—H...O inter­actions link the mol­ecules into dimers approximately along [010].

2-[4-(Tri­fluoro­meth­yl)phenyl­sulfan­yl]benzoic acid

In the title compound, C₁₄H₉F₃O₂S, the dihedral angle between the mean planes of the benzene rings is 88.7 (2)°. The carb­oxy­lic acid group is twisted by 13.6 (7)° from the mean plane of its attached aromatic ring. One of the F atoms of the tri­fluoro­methyl group is disordered over two sites in a 0.61 (7):0.39 (7) ratio. In the crystal, inversion dimers linked by pairs of O—H...O hydrogen bonds generate R₂²(8) loops. Weak C—H...F inter­actions are also observed.

N-(1H-Indol-3-yl­methyl­idene)-4-methyl­piperazin-1-amine

In the title compound, C₁₄H₁₈N₄, the piperazine ring is in a slightly distorted chair conformation. The indole ring system is twisted from the piperazine ring, making a dihedral angle of 7.27 (11)°. In the crystal, N—H...N hydrogen bonds link mol­ecules into chains along [10-1].

4-Hy­droxy-5-(2-meth­oxy­phen­oxy)-2,2′-bipyrimidin-6(5H)-one dihydrate

The title compound, C₁₅H₁₂N₄O₄·2H₂O, crystallizes with two independent water mol­ecules in the asymmetric unit. The dihedral angles between the mean planes of the benzene and pyrimidine rings and that of the pyrimidin-4-one ring are 85.1 (9) and 82.1 (1)°, respectively. The mean plane of the pyrimidine ring is twisted by 12.8 (8)° from that of the pyrimidin-4-one ring. The dihedral angles between the benzene ring and the mean planes of the pyrimidine and pyrimidin-4-one rings are 85.1 (9) and 82.1 (1)°, respectively.In the crystal, N–H...O, O—H...N and O—H...O hydrogen bonds involving both water mol­ecules are present; these link the mol­ecules into a two-dimensional network parallel to (010). In addition, weak C—H...π and π–π [centroid–centroid distance = 3.6183 (8) Å] inter­actions occur.

N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-di­hydro-1H-pyrazol-4-yl)-2-phenyl­acetamide

The title compound, C₁₉H₁₉N₃O₂, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. In mol­ecule A, the pyrazole ring adopts a slightly disordered half-chair conformation while in B it is planar [r.m.s. deviation = 0.0386 (15) Å]. The dihedral angle between the mean planes of the two phenyl rings is 56.2 (8) in A and 38.2 (3)° in B. The N-phenyl substituent on the pyrazole ring is twisted by 46.5 (2) in A and 58.6 (4)° in B while the extended phenyl ring is twisted by 82.2 (8) in A and 87.5 (9)° in B. The mean plane of the amide group forms an angle of 74.8 (3) in A and 67.7 (1)° in B with respect to the phenyl ring. In addition, the amide group is rotated by 51.4 (1) in A and 53.6 (2)° in B from the the mean plane of the pyrazole ring. In the crystal, the two molecules are linked via N—H...O hydrogen bonds, supported by weak C—H...O inter­actions, forming dimers enclosing an R₂²(10) ring motif. The dimers are linked via C—H...O inter­actions, forming a three-dimensional structure.

Raltegravir monohydrate

The hydrated title compound [systematic name: N-(4-fluoro­benz­yl)-5-hy­droxy-1-methyl-2-{1-methyl-1-[(5-methyl-1,3,4-oxa­diazol-2-ylcarbon­yl)amino]­eth­yl}-6-oxo-1,6-di­hydro­pyrimidine-4-carb­oxamide monohydrate], C₂₀H₂₁FN₆O₅·H₂O, is recognised as the first HIV integrase inhibitor. In the mol­ecule, the dihedral angles between the mean planes of the pyrimidine ring and the phenyl and oxa­diazole rings are 72.0 (1) and 61.8 (3)°, respectively. The mean plane of the oxa­diazole ring is twisted by 15.6 (3)° from that of the benzene ring, while the mean plane of amide group bound to the oxadiaole ring is twisted by 18.8 (3)° from its mean plane. Intra­molecular O—H...O and C—H...N hydrogen bonds are observed in the mol­ecule. The crystal packing features O—H...O hydrogen bonds, which include bifurcated O—H...(O,O) hydrogen bonds from one H atom of the water mol­ecule. In addition, N—H...O hydrogen bonds are observed involving the two amide groups. These inter­actions link the mol­ecules into chains along [010].

4-(3-Fluoro-4-methyl­anilino)-2-methyl­idene-4-oxo­butanoic acid

The title compound, C₁₂H₁₂FNO₃, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. The dihedral angle between the mean planes of the 3-fluoro-4-methyl­phenyl ring and the oxo­amine group is 25.7 (7)° in mol­ecule A and 71.3 (7)° in mol­ecule B, while the mean plane of the 2-methyl­idene-4-oxo­butanoic acid group is twisted by 76.2 (1)° from that of the oxo­amine group in mol­ecule A and by 76.2 (4)° in mol­ecule B. In the crystal, N—H...O and O—H...O hydrogen bonds [the latter forming an R₂²(8) graph-set motif] link the mol­ecules into a two-dimensional network parallel to the ac plane.

Ethyl 6-(4-chloro­phen­yl)-4-(4-fluoro­phen­yl)-2-oxo­cyclo­hex-3-ene-1-carboxyl­ate

The asymmetric unit of the title compound, C₂₁H₁₈ClFO₃, contains two independent mol­ecules. In one mol­ecule (A), the 4-chloro­phenyl, oxo­cyclo­hex-3-ene, carboxyl­ate, and ethyl groups were refined as disordered over two sets of sites with a 0.684 (5):0.316 (5) ratio. The cyclo­hexene ring in the disordered mol­ecule is in a slightly distorted envelope conformation for the major component (with the C atom bound to the carboxylate group being the flap atom) and in a screw-boat conformation for the minor component. In the ordered mol­ecule (B), the cyclo­hexene ring is in a half-chair conformation. The dihedral angles between the mean planes of the fluoro- and chloro-substituted benzene rings are 89.9 (7) (only the major component is considered for A) and 76.4 (7)° (B). In the crystal, inversion dimers are observed along with weak C—H...O hydrogen bonds, which form chains along [100].

4-Chloro­phenyl quinoline-2-carboxyl­ate

In the title compound, C₁₆H₁₀ClNO₂, the dihedral angle between the quinoline ring system and the benzene ring is 14.7 (5)°. The carboxyl­ate group is twisted from the mean planes of the quinoline ring system and the benzene ring by 17.7 (5) and 32.1 (4)°, respectively. In the crystal, inversion dimers are formed with the molecules linked by pairs of weak C—H...O inter­actions arising from an activated aromatic C atom adjacent to the C—Cl bond, generating R₂²(14) loops.

4-Chloro-3-methyl­phenyl quinoline-2-carboxyl­ate

In the title compound, C₁₇H₁₂ClNO₂, the dihedral angle between the mean planes of the quinoline ring system and the benzene ring is 68.7 (7)°. The mean plane of the carboxyl­ate group is twisted from the latter planes by 14.0 (1) and 80.2 (4)°, respectively. In the crystal, weak C—H...O inter­actions are observed, forming chains along [001]. In addition, π–π stacking inter­actions [centroid–centroid distances = 3.8343 (13) and 3.7372 (13)Å] occur. No classical hydrogen bonds were observed.

3,4-Di­methyl­phenyl quinoline-2-carboxyl­ate

In the title compound, C₁₈H₁₅NO₂, the dihedral angle between the mean planes of the quinoline ring system and the phenyl ring is 48.1 (5)°. The mean plane of the carboxyl­ate group is twisted from the mean planes of the latter by 19.8 (8) and 64.9 (5)°, respectively. The crystal packing features weak C—H...O inter­actions, which form chains along [010].