Tris(1,10-phenanthroline-κ²N,N′)iron(II) bis­(1,1,3,3-tetra­cyano-2-eth­oxy­propenide) hemihydrate

In the title hydrated mol­ecular salt, [Fe(C₁₂H₈N₂)₃](C₉H₅N₄O)₂·0.5H₂O, the water mol­ecule site is half-occupied. The Fe—N bond lengths within the octa­hedral tris-chelate [Fe(phen)3]²⁺ ion (phen is 1,10-phenantroline) are indicative of a low-spin d⁶ electronic configuration for the metal ion. The C—N, C—C and C—O bond lengths in the polynitrile anions indicate extensive electronic delocalization. In the crystal, the components are linked through O—H...N hydrogen bonds, forming [100] chains, as well as through Coulombic inter­actions.

2-(2,4-Dichloro­phen­oxy­meth­yl)-5-(4-methyl­phen­yl)imidazo[2,1-b][1,3,4]thia­diazole

In the title compound, C₁₈H₁₃Cl₂N₃OS, the eight atoms comprising the central imidazo/thia­diazo­lethia­diazole residue are coplanar (r.m.s. deviation = 0.009 Å). The dihedral angle of 8.72 (13)° between the dichloro­benzene and tolyl rings reflects a twist about the O—C(benzene) bond; the C_m—O—C_b—C_b torsion angle = −168.5 (2)° (m = methyl­ene C and b is benzene C). Supra­molecular tapes along the b axis are found in the crystal structure which are mediated by π–π inter­actions occurring between centrosymmetrically related thia­diazole rings [inter-ring centroid distance = 3.6907 (16) Å] and between the benzene and tolyl rings [inter-ring centroid distance = 3.7597 (16) Å].

5-(4-Fluoro­phen­yl)-3-(4-methyl­phen­yl)-4,5-dihydro-1H-pyrazole-1-carbothio­amide

The central pyrazole ring in the title compound, C₁₇H₁₆FN₃S, adopts an envelope conformation with the methine C atom bearing the 4-fluoro­phenyl substituent as the flap atom. Whereas the tolyl ring is slightly twisted out of the least-squares plane through the pyrazole ring [dihedral angle = 13.51 (11)°], the fluoro­benzene ring is almost perpendicular [dihedral angle = 80.21 (11)°]. The thio­amide group is almost coplanar with the N—N bond of the ring [N—N—C—N torsion angle = 1.2 (3)°] and the amine group forms an intra­molecular hydrogen bond with a ring N atom. In the crystal, supra­molecular double layers in the bc plane are formed via N—H...S, N—H...F and C—H...F inter­actions.

2-[5-(4-Fluoro­phen­yl)-3-(4-methyl­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia­zole

In the title compound, C₂₅H₂₀FN₃S, two independent mol­ecules comprise the asymmetric unit, which differ in the relative orientation of the fluoro­benzene ring with respect to the pyrazole ring to which it is attached [dihedral angles = 89.39 (17) and 75.23 (16)° in the two mol­ecules]. Each pyrazole ring adopts an envelope conformation with the methine C atom being the flap atom. There are additional twists in the mol­ecules, e.g. between the five-membered rings [dihedral angles = 18.23 (16) and 17.84 (16)°] and between the thia­zole and attached phenyl ring [10.26 (16) and 20.87 (15)°]. Overall, each mol­ecule has a T-shape. In the crystal, mol­ecules are connected into a three-dimensional architecture by weak C—H...π inter­actions.

3-(4-Chloro­phen­yl)-5-(4-fluoro­phen­yl)-4,5-dihydro-1H-pyrazole-1-carbothio­amide

In the title compound, C₁₆H₁₃ClFN₃S, the pyrazole ring adopts an envelope conformation with the methine C atom being the flap atom. The chloro- and fluoro­benzene rings are twisted out of the plane of the pyrazole ring [dihedral angles = 15.12 (11) and 80.55 (10)°, respectively]. The amine group is orientated towards a ring N atom, forming an intra­molecular N—H...N hydrogen bond. This H atom also forms a hydrogen bond to the F atom, which along with N—H...S hydrogen bonding leads to a supra­molecular chain along the c axis. Connections between chains of the type Cl...π lead to a layer in the bc plane.

(2E)-1-(2-Methyl-4-phenyl­quinolin-3-yl)-3-(3-methyl­thio­phen-2-yl)prop-2-en-1-one

In the title compound, C₂₄H₁₉NOS, the quinoline residue (r.m.s. deviation = 0.018 Å) is essentially orthogonal to both the phenyl [dihedral angle = 88.95 (8)°] and 2-thienyl [81.98 (9)°] rings. The carbonyl O atom lies to one side of the quinoline plane, the carbonyl C atom is almost coplanar and the remaining atoms of the chalcone residue lies to the other side, so that overall the mol­ecule has an L-shape. The conformation about the ethyl­ene bond [1.340 (2) Å] is E. In the crystal, a supra­molecular chain with the shape of a square rod aligned along the b-axis direction is sustained by C—H...π inter­actions, the π-systems being the heterocyclic rings.

(2E)-1-(2,4-Dimethyl­quinolin-3-yl)-3-phenyl­prop-2-en-1-one

Two independent mol­ecules comprise the asymmetric unit of the title compound, C₂₀H₁₇NO, which differ in the orientation of the terminal phenyl ring with respect to the quinoline ring [the dihedral angles are 75.72 (11) and 84.53 (12)° for the two mol­ecules]. The conformation about each of the ethyl­ene bonds [1.329 (3) and 1.318 (3) Å] is E. The crystal structure features a combination of C—H...N, C—H...π and π–π contacts [inter-centroid between the phenyl ring and the quinoline benzene ring is 3.6024 (19) Å], generating a three-dimensional network.

2-Methyl­sulfanyl-1,2,4-triazolo[1,5-a]quinazoline-5(4H)-thione

In the title compound, C₁₀H₈N₄S₂, comprising fused six-, six- and five-membered rings, the mol­ecule is close to being planar (r.m.s. deviation of the non-H atoms = 0.041 Å). The S-bound methyl group is folded away from the single N atom of the triazole ring and the NH group of the six-membered ring, allowing for the formation of centrosymmetric eight-membered {...HNCN}₂ synthons in the crystal. The resulting inversion dimers are connected into supra­molecular stacks aligned along the b-axis direction by π–π inter­actions [centroid–centroid distances = 3.6531 (12) and 3.7182 (12) Å].

Ethyl 2-amino-4-(4-bromo­phen­yl)-6-meth­oxy-4H-benzo[h]chromene-3-carboxyl­ate

In the title compound, C₂₃H₂₀BrNO₄, the pyran ring has a flattened boat conformation with the O and methine C atoms lying to one side of the plane [0.160 (5) and 0.256 (6) Å, respectively] defined by the remaining atoms. Nevertheless, the 4H-benzo[h]chromene ring system approximates a plane (r.m.s. deviation = 0.116 Å) with the bromo­benzene ring almost perpendicular [dihedral angle = 83.27 (16)°] and the ester group coplanar [C—C—C—O = 3.4 (5)°]; the meth­oxy substituent is also coplanar [C—O—C—C = 174.5 (3)°]. In addition to an intra­molecular N—H...O(ester carbon­yl) hydrogen bond, the ester carbonyl O atom also forms an inter­molecular N—H...O hydrogen bond with the second amine H atom, generating a zigzag supra­molecular chain along the c axis in the crystal packing. The chains are linked into layers in the bc plane by N—H...Br hydrogen bonds, and these layers are consolidated into a three-dimensional architecture by C—H...π inter­actions.

4-Dimethyl­amino-1-(4-meth­oxy­phen­yl)-2,5-dioxo-2,5-dihydro-1H-pyrrole-3-carbonitrile

In the title compound, C₁₄H₁₃N₃O₃, a twist occurs, as seen in the dihedral angle of 53.60 (12)° between the pyrrole and benzene rings. A three-dimensional architecture is formed in the crystal whereby layers of mol­ecules in the ac plane are connected by C—H...O and C—H...π inter­actions.

2-Amino-4-(4-chloro­phen­yl)-4H-chromeno[8,7-b]pyridine-3-carbonitrile

The asymmetric unit of the title compound, C₁₉H₁₂ClN₃O, contains two mol­ecules with similar conformations. The 14 non-H atoms comprising the 4H-chromeno[8,7-b]pyridine residue are essentially coplanar (r.m.s. deviations = 0.037 and 0.042 Å for the two mol­ecules) and the main difference between them is seen in the twist about the bond linking the main residue to the attached chloro­benzene rings [dihedral angles = 79.01 (12) and 76.22 (11)° for the two mol­ecules]. Zigzag supra­molecular chains along the a-axis direction mediated by amino–pyridine N—H...N hydrogen bonds feature in the crystal packing; these are connected into a three-dimensional architecture by C—H...π inter­actions and Cl...Cl contacts [Cl...Cl = 3.3896 (14) Å].

3-Amino-1-(4-fluoro­phen­yl)-8-meth­oxy-1H-benzo[f]chromene-2-carbonitrile

The title compound, C₂₁H₁₅FN₂O₂, features an approximately planar 1H-benzo[f]chromene fused-ring system (r.m.s. deviation for the 14 non-H atoms = 0.052 Å), with the fluoro­benzene ring being almost perpendicular to this [dihedral angle = 85.30 (7) °]. The furan ring has a flattened half-chair conformation, with the methine C atom deviating by 0.132 (2) Å from the plane of the remaining atoms (r.m.s. deviation = 0.0107 Å). In the crystal, inversion dimers are formed via pairs of amine–cyano N—H...N hydrogen bonds. The dimers are connected into a three-dimensional architecture by C—H...N(cyano), C—H...π and π–π [inter­centroid distance = 3.6671 (10) Å] inter­actions.

3-Amino-1-(4-fluoro­phen­yl)-7-meth­oxy-1H-benzo[f]chromene-2-carbonitrile

In the title compound, C₂₁H₁₅FN₂O₂, the furan ring has a flattened half-chair conformation [the methine C atom lies 0.136 (2) Å above the C₅ plane which has an r.m.s. deviation of 0.0229 Å]. Overall, the 1H-benzo[f]chromene fused-ring system approximates a plane (r.m.s. deviation of the 14 non-H atoms = 0.049 Å). The fluoro­benzene ring is almost perpendicular to this plane [dihedral angle = 89.58 (8)°]. Zigzag supra­molecular tapes along the b axis are the most notable feature of the crystal packing. This arises through an alternating sequence of 12-membered {...HNC₃N}₂ and eight-membered {...HNCO}₂ synthons. These are connected into a three-dimensional architecture by π–π [inter­centroid distance for centrosymmetrically related fluoro­benzene rings = 3.5181 (10) Å] and C—H...π inter­actions.

2-Amino-4-(4-bromo­phen­yl)-6-meth­oxy-4H-benzo[h]chromene-3-carbonitrile

In the title compound, C₂₁H₁₅BrN₂O₂, the 14 non-H atoms of the 4H-benzo[h]chromene fused-ring system are approximately coplanar (r.m.s. deviation = 0.129 Å). Within this system, the 4H-pyran ring adopts a flattened half-chair conformation with the methine C atom lying 0.281 (4) Å above the plane of the remaining atoms (r.m.s. deviation = 0.0446 Å). The bromo­benzene ring is almost perpendicular to the fused-ring system [dihedral angle = 85.34 (13)°]. In the crystal, supra­molecular layers parallel to (101) are sustained by amine–cyano N—H...N and amine–meth­oxy N—H...O hydrogen bonds. The layers stack with inter­actions of the type (bromo­benzene)C—H...π(outer-C₆ ring of the fused-ring system) connecting them.

N′-[3-Cyano-4-(4-fluoro­phen­yl)-6-meth­oxy-4H-benzo[h]chromen-2-yl]-N,N-dimethyl­methanimidamide

In the title compound, C₂₄H₂₀FN₃O₂, despite the 4H-pyran ring having a flattened half-chair conformation [the methine C atom lies 0.257 (3) Å above the plane of the remaining atoms with an r.m.s. deviation of 0.0295 Å], the 14 non-H atoms of the 4H-benzo[h]chromene residue are approximately coplanar (r.m.s. deviation = 0.081 Å). The benzene ring is nearly perpendicular to this plane [dihedral angle = 76.18 (10)°], but the planar (r.m.s. deviation = 0.033 Å) dimethyl­methanimidamide substituent is coplanar [dihedral angle = 1.96 (12)°]. In the crystal, centrosymmetric dimeric aggregates arise from C—H...N inter­actions, and these are connected into supra­molecular layers in the ab plane by C—H...π and π–π [inter­centroid (central C₆ ring)...(outer C₆ ring)ⁱ distance = 3.8564 (14) Å] inter­actions.

2-(4-Fluoro­benzyl­idene)propane­dinitrile: monoclinic polymorph

The title compound, C₁₀H₅FN₂, is a monoclinic (P2₁/c) polymorph of the previously reported triclinic (P-1) form [Anti­pin et al. (2003). J. Mol. Struct. 650, 1–20]. The 13 non-H atoms in the title polymorph are almost coplanar (r.m.s. deviation = 0.020 Å); a small twist between the fluoro­benzene and dinitrile groups [C—C—C—C torsion angle = 175.49 (16)°] is evident in the triclinic polymorph. In the crystal, C—H...N inter­actions lead to supra­molecular layers parallel to (-101); these are connected by C—F...π inter­actions.

3,3-Bis(4-bromo­phenyl­sulfan­yl)-1-methyl­piperidin-2-one

In the title compound, C₁₈H₁₇Br₂NOS₂, the conformation of the piperidin-2-one ring is based on a half-chair with the methyl­ene C atom diagonally opposite the N atom being 0.649 (3) Å above the plane of the remaining five atoms (r.m.s. deviation = 0.1205 Å). The S atoms occupy axial and bis­ectional positions, and the dihedral angle between the benzene rings of 59.95 (11)° indicates a splayed disposition. Helical supra­molecular chains along the b axis sustained by C—H...O inter­actions is the major feature of the crystal packing. The chains are connected into a three-dimensional architecture by C—H...Br and C—H...π inter­actions.

2-[3-(4-Chloro­phen­yl)-5-(4-fluoro­phenyl)-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia­zole

In the title compound, C₂₄H₁₇ClFN₃S, the pyrazole ring is almost planar (r.m.s. deviation = 0.030 Å). With the exception of the methine-bound benzene ring, which forms a dihedral angle of 85.77 (13)° with the pyrazole ring, the remaining non-C atoms lie in an approximate plane (r.m.s. deviation = 0.084 Å) so that overall the mol­ecule has a T-shape. In the crystal, centrosymmetrically related mol­ecules are connected via π–π inter­actions between pyrazole rings [centroid–centroid distance = 3.5370 (15) Å] and these stack along the a axis with no specific inter­actions between them.

5-Methyl-N′-[(3Z)-2-oxo-2,3-dihydro-1H-indol-3-yl­idene]-1-phenyl-1H-1,2,3-triazole-4-carbohydrazide

In the title compound, C₁₈H₁₄N₆O₂, the benzene ring is slightly twisted out of the plane of the 1,2,3-triazole ring (r.m.s. deviation = 0.010 Å), forming a dihedral angle of 6.20 (13)°. The nine non-H ring atoms of the fused five- and six-membered ring system are almost coplanar (r.m.s. deviation = 0.032 Å). The near coplanarity in the central residue is consolidated by an intra­molecular bifurcated N—H...(O,N) hydrogen bond. The conformation about the N=C bond is Z. In the crystal, supra­molecular chains along [101] are sustained by N—H...O hydrogen bonds and C—H...O inter­actions. These are consolidated into a three-dimensional architecture by C—H...π and π–π inter­actions; the latter occur between centrosymmetrically related 1,2,3-triazole rings [centroid–centroid distance = 3.6056 (14) Å].

Di­chlorido­{2-[(E)-phen­yl(pyridin-2-yl-κN)methyl­idene]-N-phenyl­hydra­zine­carboxamide-κ²N²,O}copper(II)

The title compound, [CuCl₂(C₁₉H₁₆N₄O)], contains a Cu^II atom N,N′,O-chelated by a neutral N-phenyl­hy­dra­zine­car­box­amide ligand and additionally coordinated by two Cl atoms, resulting in a distorted square-pyramidal geometry. The ligating atoms in the basal square plane of the complex comprise the azomethine N, the pyridine N, the amide O and one of the Cl atoms, whereas the other Cl atom occupies an apical position. The apical Cl atoms in adjacent layers function as hydrogen-bond acceptors to both NH groups. Intermolecular C—H...Cl and C—H...O interactions are also observed.

4-[5-(4-Fluoro­phen­yl)-1-(4-phenyl-1,3-thia­zol-2-yl)-4,5-dihydro-1H-pyrazol-3-yl]-5-methyl-1-(4-methyl­phenyl)-1H-1,2,3-triazole

In the title compound, C₂₈H₂₃FN₆S, the pyrazole ring adopts an envelope conformation, with the methine C atom being the flap atom. With respect to this ring, the 2-thienyl, triazole and fluoro­benzene rings are approximately coplanar, coplanar and perpendicular, respectively [dihedral angles = 8.56 (17), 6.03 (19) and 73.1 (2)°, respectively] so that to a first approximation the mol­ecule has a T-shape. In the crystal, mol­ecules are consolidated into a three-dimensional architecture by C—H...F (involving a bifurcated F atom), C—H...S and C—H...π inter­actions.

5-(4-Fluoro­phen­yl)-3-[5-methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazol-4-yl]-N-phenyl-4,5-dihydro-1H-pyrazole-1-carbothio­amide

In the title compound, C₂₆H₂₃FN₆S, the pyrazole ring has an envelope conformation, with the methine C atom being the flap atom. The thio­urea group is close to being coplanar with the pyrazole N atoms [N—N—C—S torsion angle = 176.78 (15)°], which allows for an intra­molecular N—H...N hydrogen bond; the connected triazole ring is nearly coplanar with this ring [N—C—C—N = −172.65 (19)°]. There is a significant twist between the pyrazole ring and attached fluoro­benzene ring [N—C—C—C = −18.8 (3)°] and a greater twist between triazole and attached tolyl ring [dihedral angle = 58.25 (14)°]. In the crystal, supra­molecular chains aligned along [40,10] are consolidated by π–π inter­actions between the triazole and phenyl rings [centroid–centroid distance = 3.7053 (13) Å].

Di-μ-iodido-bis­(iodido­{methyl 4-[(pyridin-2-yl­methyl­idene)amino]­benzoate-κ²N,N′}cadmium)

The complete binuclear molecule of the title compound, [Cd₂I₄(C₁₄H₁₂N₂O₂)₂], is generated by the application of a centre of inversion. The Cd—I bond lengths of the central core are close and uniformly longer than the exocyclic Cd—I bond. The coordination sphere of the Cd^II atom is completed by two N atoms of a chelating methyl 4-[(pyridin-2-yl­methyl­idene)amino]­benzoate ligand, and is based on a square pyramid with the terminal I atom in the apical position. The three-dimensional crystal packing is stabilized by C—H...O and C—H...π inter­actions, each involving the pyridine ring.

(2-{[4-(Chlorido­mercur­yl)phen­yl]imino­meth­yl}pyridine-κ²N,N′)di­iodido­mercury(II) dimethyl sulfoxide monosolvate

The title dimethyl sulfoxide solvate, [Hg₂(C₁₂H₉ClN₂)I₂]·C₂H₆OS, features tetra­hedrally and linearly coordinated Hg^II atoms. The distorted tetrahedral coordination sphere is defined by chelating N atoms that define an acute angle [69.6 (3)°] and two I atoms that form a wide angle [142.80 (4)°]. The linearly coordinated Hg^II atom [177.0 (4)°] exists with a donor set defined by C and Cl atoms. Secondary inter­actions are apparent in the crystal packing with the tetra­hedrally and linearly coordinated Hg^II atoms expanding their coordination environments by forming weak Hg...I [3.772 (7) Å] and Hg...O [2.921 (12) Å] inter­actions, respectively. Mercury-containing mol­ecules stack along the a axis, are connected by π–π inter­actions [inter-centroid distance between pyridine and benzene rings = 3.772 (7) Å] and define channels in which the dimethyl sulfoxide mol­ecules reside. The latter are connected by the aforementioned Hg...O inter­actions as well as C—H...I and C—H...O inter­actions, resulting in a three-dimensional architecture.

(2E)-3-(4-Fluoro­phen­yl)-1-[5-methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazol-4-yl]prop-2-en-1-one

With respect to the triazole ring in the title compound, C₁₉H₁₆FN₃O, the p-tolyl ring is inclined [dihedral angle = 51.79 (11)°], whereas the chalcone residue is almost coplanar [O—C—C—N and C—C—C—C torsion angles = −178.71 (19) and 178.42 (18)°, respectively]. The conformation about the C=C bond [1.328 (3) Å] is E, and the triazole methyl group and the carbonyl O atom are syn. In the crystal, centrosymmetrically related mol­ecules are connected by π–π inter­actions between the triazole and p-tolyl rings [centroid–centroid distance = 3.6599 (12) Å] and these are linked into a three-dimensional architecture by C—H...N and C—H...π inter­actions.

(2E)-1-[5-Methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazol-4-yl]-3-[4-(piperidin-1-yl)phen­yl]prop-2-en-1-one

Two independent mol­ecules comprise the asymmetric unit of the title compound, C₂₄H₂₆N₄O. The major difference between them is found in the relative orientation of the triazole-bound p-tolyl group which have the opposite sense of twist [N—N—C—C torsion angles = 55.8 (3) and −49.8 (3)°]. The chalcone residue is almost coplanar with the triazole ring [N—C—C—O and C—C—C—C torsion angles = −178.9 (2) and −178.5 (2)°, respectively; cf. 177.9 (3) and 168.5 (3)°, respectively, in the second mol­ecule]. The conformation about each C=C double bond is E and in each case the triazole methyl group is syn to the carbonyl O atom. In the crystal, mol­ecules aggregate into layers parallel to (-113). The first independent mol­ecule self-associates into a layer via C—H...O and C—H...π inter­actions. By contrast, layers comprising the second independent mol­ecule do not feature specific inter­actions between mol­ecules. The global crystal packing comprises alternating layers.

5-(Adamantan-1-yl)-N-methyl-1,3,4-thia­diazol-2-amine

In the title compound, C₁₃H₁₉N₃S, the methyl­amine substituent is coplanar with the thia­diazole ring to which it is attached [C—N—C—S torsion angle = 175.9 (2)°] and the amine H atom is syn to the thia­diazole S atom. Supra­molecular chains along [101], sustained by N—H...N hydrogen bonding, feature in the crystal packing.

3-[(4-Phenyl­piperazin-1-yl)meth­yl]-5-(thio­phen-2-yl)-2,3-di­hydro-1,3,4-oxa­diazole-2-thione

In the title compound, C₁₇H₁₈N₄OS₂, the 2-thienyl ring is disordered over two co-planar, opposite orientations in a 0.684 (2): 0.316 ratio. The 1,3,4-oxa­diazole ring is almost co-planar with the attached 2-thienyl ring [dihedral angles of 5.34 (19) and 4.8 (5)° for the major and minor components, respectively]. The relative disposition of the thione- and ring-S atoms is anti for the major orientation of the 2-thienyl residue. Overall, the shape of the mol­ecule approximates the letter V. In the crystal, a three-dimensional architecture is consolidated by a combination of weak C—H...S and C—H...π contacts.

3-(Adamantan-1-yl)-4-[(E)-(2,6-di­fluoro­benzyl­idene)amino]-1-[(4-ethyl­piperazin-1-yl)meth­yl]-4,5-di­hydro-1H-1,2,4-triazole-5-thione

In the title compound, C₂₆H₃₄F₂N₆S, the triazole ring is linked to a benzene ring via an imine bond [N=C = 1.255 (2) Å; conformation: E], with a dihedral angle of 25.21 (11)° between the rings. The 4-ethyl­piperazinyl residue is folded away from the thione-S atom. In the crystal, helical supra­molecular chains propagating along [010] and sustained by weak C—S...π(triazole) inter­actions occur [S...centroid distance = 3.2872 (10) Å]. Links between these chains are of the type benzene-C—H...N(imine) and π–π [between centrosymmetrically related benzene rings with an inter-centroid distance of 3.9241 (15) Å] and result in a three-dimensional architecture.

3-(Adamantan-1-yl)-4-methyl-1-({4-[3-(tri­fluoro­meth­yl)phen­yl]piperazin-1-yl}meth­yl)-4,5-di­hydro-1H-1,2,4-triazole-5-thione

In the title compound, C₂₅H₃₂F₃N₅S, two independent mol­ecules comprise the asymmetric unit and are related across a pseudo-centre of inversion. The piperazine rings have chair conformations with each N-bound substituent occupying an equatorial position so that the dihedral angles between the planes of the triazole and benzene ring are 78.20 (19) and 79.10 (19)° for the two independent mol­ecules, indicating that the mol­ecules have an L-shape. In the crystal, a three-dimensional architecture is stabilized by C—H...π inter­actions. The crystal studied was an inversion twin with the fractional contribution of the minor component being 0.27 (9).

4-Benzyl-3-(thio­phen-2-yl)-4,5-di­hydro-1H-1,2,4-triazole-5-thione

In the title compound, C₁₃H₁₁N₃S₂, the triazole and thio­phene rings are coplanar [dihedral angle = 6.22 (13)°]. By contrast, the phenyl ring is perpendicular to the triazole ring [dihedral angle = 85.58 (13)°], so that the mol­ecule has an L-shape. The thio­phene S atom is syn with the ring imine N atom. In the crystal, eight-membered {...HNCS}₂ synthons form between centrosymmetrically related mol­ecules, leading to dimeric aggregates that are connected into a supra­molecular layer parallel to (101) by π–π inter­actions between centrosymmetrically related triazole rings [centroid–centroid distance = 3.6091 (15) Å] and C—H...π inter­actions.

5-(Adamantan-1-yl)-3-anilinomethyl-2,3-di­hydro-1,3,4-oxa­diazole-2-thione

In the title compound, C₁₉H₂₃N₃OS, the oxa­diazole and benzene rings are inclined at a dihedral angle of 50.30 (11)°, with the major twist between them occurring at the ring–methyl­ene N—C bond [N—N—C—N torsion angle = −101.2 (2)°]. In the crystal, helical supra­molecular chains along [010] are sustained by N—H...S hydrogen bonds. These are linked into layers lying parallel to (-101) by methyl­ene–phenyl C—H...π inter­actions.

5-(Adamantan-1-yl)-3-[(4-fluoro­anilino)meth­yl]-2,3-di­hydro-1,3,4-oxa­diazole-2-thione

In the title compound, C₁₉H₂₂FN₃OS, the dihedral angle between the inclined oxa­diazole and benzene rings is 52.7 (3)°. In the crystal, helical supra­molecular chains along [100] are sustained by N—H...S hydrogen bonds supported by methyl­ene–benzene C—H...π inter­actions. The crystal studied was an inversion twin with the fractional contribution of the minor component being 0.33 (14).

2-[3-(4-Bromo­phenyl)-5-(4-fluoro­phenyl)-4,5-di­hydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia­zole

In the title compound, C₂₄H₁₇BrFN₃S, the pyrazole ring is almost planar (r.m.s. deviation = 0.043 Å), with all but the perpendicular fluoro­benzene ring substituents [dihedral angle = 77.9 (3)°] being very approximately coplanar [dihedral angle with the 2-thienyl ring = 19.4 (3)° and with the bromo­benzene ring = 20.3 (3)°; dihedral angle between the 2-thienyl and attached phenyl ring = 11.0 (4)°], so that the mol­ecule has a T-shape. In the crystal, supra­molecular chains along the b-axis direction are sustained by C—H...S and C—Br...π inter­actions.

2-Meth­oxy-4-(prop-2-en-1-yl)phenyl 4-meth­oxy­benzoate

In the title compound, C₁₈H₁₈O₄, the planes of the benzene rings are twisted by 81.60 (5)°. In the crystal, weak C—H...O hydrogen bonds link the mol­ecules into supra­molecular chains extending along the a axis.

Carbamo­yl(di­amino­methyl­idene)aza­nium 3-nitro-5-oxo-4,5-di­hydro-1H-1,2,4-triazol-4-ide

In the anion of the title salt, C₂H₇N₄O⁺·C₂HN₄O₃⁻, the negative charge resides formally on the N³ atom of the triazole ring. In the crystal, the N³ and exocyclic O atoms are hydrogen-bond acceptors with respect to the formally double-bond iminium and amido N atoms of the cation. The cation and anion are almost planar (r.m.s. deviations = 0.012 and 0.051 Å, respectively), but they are slightly bent with respect to each other [dihedral angle = 12.6 (1)°]. In the crystal, adjacent anions and cations are linked by extensive N—H...N and N—H...O hydrogen bonds, generating a ribbon running along the b-axis direction.

2-Meth­oxy-4-(prop-2-en-1-yl)phenyl benzoate

In the title compound, C₁₇H₁₆O₃, the benzene rings are twisted by 63.54 (5)°. The twist is similar to that found in the unsubstituted compound, phenyl benzoate. The crystal packing features C—H...O hydrogen bonds.

2-Meth­oxy-4-(prop-2-en-1-yl)phenyl 2,4-di­chloro­benzoate

In the title compound, C₁₇H₁₄Cl₂O₃, the two benzene rings are twisted by 73.6 (2)°. The twist is similar to that found in the unsubstituted compound, viz. phenyl benzoate. In the crystal, inversion dimers are linked by pairs of C—H...O inter­actions.

3-Acetyl-2,4-di­methyl­quinolin-1-ium chloride

In the title salt, C₁₃H₁₄NO⁺·Cl⁻, the dihedral angle between the fused ring system (r.m.s. deviation = 0.039 Å) and the attached aldehyde group is 75.27 (16)°. In the crystal, the cation and anion are linked by an N—H...Cl hydrogen bond and the resulting pairs are connected into four-ion aggregates by π–π inter­actions between the C₆ and pyridinium rings [3.6450 (9) Å] of inversion-related quinolinium residues.

(2E)-1-(4-Bromo­phen­yl)-3-[3-(4-meth­oxy­phen­yl)-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one

The pyrazole ring in the title compound, C₂₅H₁₉BrN₂O₂, is almost planar (r.m.s. deviation = 0.003 Å) and forms dihedral angles of 7.56 (13) and 56.48 (13)° with the N- and C-bound benzene rings, respectively. The prop-2-en-1-one residue has an E conformation about the C=C double bond [1.328 (4) Å] and is almost coplanar with the pyrazole ring [C—C—C—C torsion angle = −174.4 (3)°]. A twist between the prop-2-en-1-one unit and the terminal benzene ring is evident [C—C—C—C torsion angle = −15.4 (4)°]. In the crystal, mol­ecules are consolidated into a three-dimensional architecture by C—H...O, C—H...π and π–π [centroid–centroid separation = 3.7597 (16) Å] inter­actions.

Pallidol hexa­acetate ethyl acetate monosolvate

The entire mol­ecule of pallidol hexa­acetate {systematic name: (±)-(4bR,5R,9bR,10R)-5,10-bis­[4-(acet­yloxy)phen­yl]-4b,5,9b,10-tetra­hydro­indeno­[2,1-a]indene-1,3,6,8-tetrayl tetra­acetate} is completed by the application of twofold rotational symmetry in the title ethyl acetate solvate, C₄₀H₃₄O₁₂·C₄H₈O₂. The ethyl acetate mol­ecule was highly disordered and was treated with the SQUEEZE routine [Spek (2009). Acta Cryst. D65, 148–155]; the crystallographic data take into account the presence of the solvent. In pallidol hexa­acetate, the dihedral angle between the fused five-membered rings (r.m.s. deviation = 0.100 Å) is 54.73 (6)°, indicating a significant fold in the mol­ecule. Significant twists between residues are also evident as seen in the dihedral angle of 80.70 (5)° between the five-membered ring and the pendent benzene ring to which it is attached. Similarly, the acetate residues are twisted with respect to the benzene ring to which they are attached [C—O(carb­oxy)—C—C torsion angles = −70.24 (14), −114.43 (10) and −72.54 (13)°]. In the crystal, a three-dimensional architecture is sustained by C—H...O inter­actions which encompass channels in which the disordered ethyl acetate mol­ecules reside.

3-({[Bis(2-methyl­prop­yl)carbamo­thio­yl]amino}­carbon­yl)benzamide

In the title compound, C₁₇H₂₅N₃O₂S, the terminal and central amide groups are, respectively, twisted and coplanar with the attached benzene ring [O—C—C—C torsion angles = 22.7 (3) and 5.4 (3)°]. In the central part of the mol­ecule, the amide and thio­amide residues are approximately perpendicular [C—N—C—S torsion angle = −104.98 (18)°]. Supra­molecular layers with a zigzag topology are formed in the crystal packing by N—H...O, N—H...S and C—H...O inter­actions; these stack along c, being separated by hydro­phobic inter­actions.

3-{[(Di­benzyl­carbamo­thio­yl)amino]­carbon­yl}benzamide

Two independent mol­ecules with quite similar conformations, A and B, comprise the asymmetric unit of the title compound, C₂₃H₂₁N₃O₂S. The terminal amide substituent is coplanar with the attached benzene ring [the O—C—C—C torsion angles are 174.0 (2) (A) and 6.3 (3)° (B)]. In the same way, the central amide group [C—C—C—O = 7.8 (3) (A) and 11.5 (3)° (B)] is approximately coplanar with the ring to which it is attached. A major twist is noted between the amide and adjacent thio­amide residues [C—N—C—S = −109.29 (19) (A) and −112.29 (19)° (B)]. In the crystal, supra­molecular chains along [100] are formed by N—H...O and N—H...S hydrogen bonding. These are connected into a three-dimensional architecture by C—H...π and π–π inter­actions [inter-centroid distance = 3.9157 (12) Å].

(2E)-3-(6-Chloro-2-meth­oxy­quinolin-3-yl)-1-(2,4-di­methyl­quinolin-3-yl)prop-2-en-1-one

The mol­ecule of the title compound, C₂₄H₁₉ClN₂O₂, is bent, with the dihedral angle between the terminal quinoline ring systems being 63.30 (5)°. The quinolinyl residues are connected by an almost planar prop-2-en-1-one bridge (r.m.s. deviation = 0.022 Å), with the dihedral angles between this plane and the appended quinolinyl residues being 75.86 (7) and 38.54 (7)°. The C atom of the meth­oxy group is close to coplanar with its attached ring [deviation = 0.116 (2) Å]. In the crystal, a three-dimensional architecture is constructed by meth­yl–carbonyl C—H...O inter­actions and π–π inter­actions between centrosymmetrically related quinolinyl residues [centroid-to-centroid separations 3.5341 (10) and 3.8719 (9) Å].

(2E)-3-(2-Chloro-8-methyl­quinolin-3-yl)-1-(2,4-di­methyl­quinolin-3-yl)prop-2-en-1-one

In the mol­ecule of the title compound, C₂₄H₁₉ClN₂O, the terminal quinolinyl residues are close to perpendicular to each other [dihedral angle 83.72 (4)°]. The quinolinyl residues are connected by and inclined to the prop-2-en-1-one bridge, with the C_ar—C_ar—C—C (ar = aromatic) torsion angles being 71.01 (17) and 20.6 (2)°. The crystal structure features phen­yl–carbonyl C—H...O inter­actions and π–π inter­actions between centrosymmetrically related quinolinyl residues [3.5341 (10) and 3.8719 (9) Å], which together lead to a three-dimensional architecture.

(2E)-3-(2-Chloro-8-methyl­quinolin-3-yl)-1-(2-methyl-4-phenyl­quinolin-3-yl)prop-2-en-1-one

In the title compound, C₂₉H₂₁ClN₂O, there is a twist in the bridging prop-2-en-1-one group [C=C—C=O torsion angle = 22.7 (2)°]. The quinolinyl residues form a dihedral angle of 86.92 (4)°, indicating an almost perpendicular relationship. In the crystal, supra­molecular layers in the bc plane are stabilized by C—H...π and π–π inter­actions [centroid–centroid distance = 3.4947 (7) Å].

(2E)-3-(6-Chloro-2-meth­oxy­quinolin-3-yl)-1-(2-methyl-4-phenyl­quinolin-3-yl)prop-2-en-1-one acetone monosolvate

In the title solvate, C₂₉H₂₁ClN₂O₂·C₃H₆O, a prop-2-en-1-one bridge links two quinolinyl residues; the latter are almost perpendicular [dihedral angle = 78.27 (6)°]. The dihedral angle between the quinonyl ring system and its pendant phenyl group is 59.78 (8)°. A small twist in the bridging prop-2-en-1-one group is noted [O=C—C=C torsion angle = −10.6 (3)°]. In the crystal, a three-dimensional architecture arises as a result of C—H...O and π–π stacking [centroid–centroid distances = 3.5504 (12)–3.6623 (12) Å].

1-[3-({[Bis(2-methyl­prop­yl)carbamo­thio­yl]amino}­carbon­yl)benzoyl]-3,3-bis­(2-methyl­prop­yl)thio­urea

The title compound, C₂₆H₄₂N₄O₂S₂, adopts a shallow U-shape as both pendant arms of the 1,3-substituted benzene ring are orientated in the same direction. The thione S atoms lie to the same side of the benzene ring and the carbonyl O atoms to the other. The most prominent feature of the crystal packing is the formation of inversion dimers mediated by N—H...S hydrogen bonds. One of the 2-methyl­propyl groups is statistically disordered over two positions.

(2E)-3-(2-Chloro­benzo[h]quinolin-3-yl)-1-(2-methyl-4-phenyl­quinolin-3-yl)prop-2-en-1-one

In the title compound, C₃₂H₂₁ClN₂O, an almost planar (r.m.s. deviation = 0.033 Å) prop-2-en-1-one bridge links quinolinyl and benzoquinolinyl residues; the latter are twisted out of the plane of the bridge [dihedral angles = 75.94 (5) and 20.20 (5)°, respectively]. In the crystal, a three-dimensional architecture arises as a result of C—H...O, C—H...π and π–π [centroid–centroid distances involving pyridine rings = 3.5806 (7)–3.7537 (7) Å] interactions.

(2E)-3-(2-Chloro-7-methyl­quinolin-3-yl)-1-(6-chloro-2-methyl-4-phenyl­quinolin-3-yl)prop-2-en-1-one ethanol monosolvate

In the title ethanol solvate, C₂₉H₂₀Cl₂N₂O·C₂H₅OH, the quinolinyl residues form a dihedral angle of 46.41 (4)° with each other, and each is inclined [C_p—C—C=O and C=C—C—C_p (p = pyridyl) torsion angles = 54.8 (2) and 144.44 (19)°, respectively] with respect to the almost planar bridging prop-2-en-1-one residue [O=C—C=C torsion angle = −4.1 (3)°]. The ethanol solvent mol­ecule is disordered over two positions of equal occupancy and is located close to a centre of inversion. These mol­ecules reside in cavities defined by the organic mol­ecules, which are connected into a three-dimensional architecture by C—H...Cl, C—H...O and C—H...N inter­actions, as well as π–π contacts [inter-centroid distances = 3.5853 (10) and 3.8268 (11) Å], each involving pyridyl rings.

A second monoclinic polymorph of 3,5-di-tert-butyl-2-hy­droxy­benzaldehyde

In the title mol­ecule, C₁₅H₂₂O₂, there is an intra­molecular hydrogen bond involving the hy­droxy and aldehyde groups and forming an S(6) ring. The mean plane of the non-H atoms of this ring [(H)O—C[pdbond]C—C=O, with a maximum deviation of 0.013 (1) Å] are essentially coplanar with the benzene ring, forming a dihedral angle of 2.29 (8)°.

Ethyl (2Z)-3-oxo-2-(3,4,5-tri­meth­oxy­benzyl­idene)butano­ate

In the title compound, C₁₆H₂₀O₆, the conformation about the C=C double bond [1.344 (2) Å] is Z. With respect to this bond, the ketone is almost coplanar [C—C—C—O torsion angle = −179.60 (10)°] and the ester is almost perpendicular [C—C—C—O = 78.42 (13)°]. The meth­oxy substituents of the central benzene ring are either almost coplanar [C—C—O—C = 3.54 (15) and 177.70 (9)°] or perpendicular [C—C—O—C = 80.08 12)° for the central substituent]. In the crystal, the three-dimensional architecture features C—H...O and π–π [inter-centroid distance = 3.6283 (6) Å] inter­actions.