6-(3,5-Dimethyl­benz­yl)-5-ethyl-1-[(3-phenyl­prop­oxy)meth­yl]-1,2,3,4-tetra­hydro­pyrimidine-2,4-dione

The pyrimidine ring of the title compound, C₂₅H₃₀N₂O₃, is approximately planar (r.m.s. deviation = 0.003 Å); the C atom at the 5-position deviates by 0.012 (3) Å from the mean plane and the C atom at the 6-position by 0.038 (3) Å. In the mol­ecule, the pyrimidine ring is oriented at 86.72 (9) and 59.75 (9)° with respect to the two benzene rings, and the two benzene rings are inclined to each other at 58.35 (9)°. In the crystal, the amino group is hydrogen-bond donor to the exocyclic O atom at the 4-position of an adjacent mol­ecule, the hydrogen bond generating an inversion dimer.

2-Eth­oxy­methyl-6-ethyl-2,3,4,5-tetra­hydro-1,2,4-triazine-3,5-dione

The 1,2,4-triazine ring of the title compound, C₈H₁₃N₃O₃, is nearly planar (r.m.s. deviation = 0.019 Å). The imino group is hydrogen-bond donor to the exocyclic O atom at the 5-position of an adjacent mol­ecule, the N—H...O hydrogen bond generating a chain parallel to the b axis.

2-{[(2-Methyl­prop-2-en-1-yl)­oxy]meth­yl}-6-phenyl-2,3,4,5-tetra­hydro-1,2,4-triazine-3,5-dione

The 1,2,4-triazine ring in the title compound, C₁₄H₁₅N₃O₃, is approximately planar (r.m.s. deviation = 0.019 Å); the C atom at the 6-position deviates by 0.026 (2) Å from the mean plane whereas the C atom at the 2-position deviates by 0.166 (4) Å in the opposite direction. The triazine ring is oriented at 8.60 (13)° with respect to the phenyl ring. The imino group is hydrogen-bond donor to the exocyclic O atom at the 3-position of an adjacent mol­ecule, the hydrogen bond generating an inversion dimer.

1-[(Cyclo­propyl­meth­oxy)meth­yl]-5-ethyl-6-(4-methyl­benzyl)-1,2,3,4-tetra­hydro­pyrimidine-2,4-dione

The pyrimidine ring in the title compound, C₁₉H₂₄N₂O₃, is nearly planar (r.m.s. deviation = 0.008 Å); the C atom at the 5-position deviates by 0.054 (3) Å from the mean plane and the C atom at the 6-position by 0.006 (3) Å in the opposite direction. The benzene ring is approximately perpendicular to the pyrimidine ring [dihedral angle = 83.90 (10)°]. The amino group is hydrogen-bond donor to the exocyclic O atom at the 2-position of an adjacent mol­ecule, the hydrogen bond generating an inversion dimer. The cyclo­propyl ring is disordered over two sets of sites with the major component having 71.5 (4)% occupancy.

1-[(Cyclo­propyl­meth­oxy)meth­yl]-6-(3,4-dimeth­oxy­benzyl)-5-ethyl-1,2,3,4-tetra­hydro­pyrimidine-2,4-dione ethanol hemisolvate

The asymmetric unit of the compound, C₂₀H₂₆N₂O₅·0.5C₂H₅OH, consists of two tetra­hydro­pyrimidine-2,4-dione mol­ecules and an ethanol mol­ecule. The pyrimidine rings are nearly planar (r.m.s. deviation = 0.006 Å in one mol­ecule and 0.009 Å in the other); the C atom at the 5-position deviates by 0.083 (3) Å [0.064 (3) Å in the second mol­ecule] from the mean plane and the C atom at the 6-position by 0.034 (3) Å [0.082 (3) Å in the second mol­ecule]. In each mol­ecule, the benzene ring is nearly perpendicular to the pyrimidine ring, the dihedral angle is 88.51 (8)° in one mol­ecule and 84.70 (8)° in the other. The amino group of each tetra­hydro­pyrimidine-2,4-dione mol­ecule is a hydrogen-bond donor to the exocyclic O atom at the 2-position of an adjacent mol­ecule, the hydrogen bond generating an inversion dimer in each case. The ethanol mol­ecule forms a hydrogen bond to the meth­oxy O atom of one of two independent mol­ecules.

4-Benzyl-N-methyl­piperazine-1-carbothio­amide

The asymmetric unit in the title thio­urea derivative, C₁₃H₁₉N₃S, comprises three independent mol­ecules (A, B and C). The thio­urea groups are superimposable for the three mol­ecules, but there are significant conformational differences. Mol­ecules A and B are approximate mirror images of each other, and mol­ecule C has an inter­mediate conformation. The dihedral angles between the thio­urea groups and the phenyl rings are 52.10 (5), 63.29 (5) and 66.46 (6)° in mol­ecules A, B and C, respectively. Each independent mol­ecule self-associates into a supra­molecular chain along [100] via N—H...S hydrogen bonds. Mol­ecules of A and B assemble into layers four mol­ecules thick in the ac plane via C—H...S and C—H...π inter­actions. Mol­ecules of C self-assemble into layers in the ac plane via C—H...S inter­actions. The layers stack along the b axis with no specific inter­actions between them.

2-(Adamantan-1-yl)-5-(4-nitro­phen­yl)-1,3,4-oxadiazole

The title mol­ecule, C₁₈H₁₉N₃O₃, lies on a mirror plane that bis­ects the adamantyl group. In the crystal, C—H...O and C—H...N inter­actions lead to supra­molecular chains along [100]. These assemble into layers in the ab plane via π–π inter­actions [centroid–centroid distance = 3.6548 (7) Å] between the oxadiazole and benzene rings.

5-Meth­oxy-1-[(5-meth­oxy-1H-indol-2-yl)meth­yl]-1H-indole

In the title compound, C₁₉H₁₈N₂O₂, the two indole ring systems are essentially planar [maximum deviation = 0.015 (2) Å in both indole ring systems] and make a dihedral angle of 72.17 (7)° with each other. In the crystal, the mol­ecules are linked into a zigzag chain along the a axis via N—H...O hydrogen bonds.

6-(3,5-Dimethyl­benz­yl)-5-ethyl-1-[(2-phenyl­eth­oxy)meth­yl]pyrimidine-2,4(1H,3H)dione

In the title pyrimidine derivative, C₂₄H₂₈N₂O₃, the uracil unit is essentially planar with an r.m.s. deviation of 0.0054 (1) Å for the eight non-H atoms. The pyrimidine ring is tilted by a dihedral angle of 77.08 (7)° with respect to the aromatic ring of the 3,5-dimethyl­benzyl substituent, whereas it is nearly parallel to the benzene ring of the pheneth­oxy­methyl unit, with a dihedral angle of 8.17 (8)°. An intra­molecular C—H...O hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are linked by a pair of amide–uracil N—H...O hydrogen bonds into an inversion R₂²(8) dimer. These dimers are stacked along the b axis through π–π inter­actions with a centroid–centroid distance of 3.9517 (8) Å. Weak C—H...π inter­actions are also present.

3-(Adamantan-1-yl)-4-ethyl-1H-1,2,4-triazole-5(4H)-thione

In the title compound, C₁₄H₂₁N₃S, the 1,2,4-triazole ring is nearly planar, with a maximum deviation of 0.003 (4) Å. In the crystal, mol­ecules are linked into inversion dimers by pairs of N—H...S hydrogen bonds.

2-[(2-Meth­oxy­eth­yl)sulfan­yl]-4-(2-methyl­prop­yl)-6-oxo-1,6-dihydro­pyrimidine-5-carbonitrile

In the title compound, C₁₂H₁₇N₃O₂S, the 4-methyl-2-methyl­sulfanyl-6-oxo-1,6-dihydro­pyrimidine-5-carbonitrile part of the mol­ecule is almost planar (r.m.s deviation = 0.062 Å). In the crystal, mol­ecules form centrosymmetric dimers via pairs of N—H...O hydrogen bonds.

3-(1-Adamant­yl)-4-amino-1-(2-benzoyl-1-phenyl­eth­yl)-1H-1,2,4-triazol-5(4H)-thione

In the title compound, C₂₇H₃₀N₄OS, the 3-(adamantan-1-yl)-4-amino-1H-1,2,4-triazole-5(4H)-thione unit and the O atom are each disordered over two sets of sites with refined site-occupancies of 0.7630 (13) and 0.2370 (13). The 1,2,4-triazole ring of the major component forms dihedral angles of 62.61 (17) and 61.93 (16)° with the benzene rings, while that of the minor component makes corresponding angles of 86.3 (4) and 79.1 (4)°. The dihedral angle between the benzene rings is 39.21 (16)°. The mol­ecular structure is stabilized by an intra­molecular C—H...N hydrogen bond, which generates an S(6) ring motif. In the crystal, mol­ecules are linked into inversion dimers by pairs of N—H...S hydrogen bonds.

1-(Adamantan-1-yl)-3-(4-fluoro­phen­yl)thio­urea

In the title mol­ecule, C₁₇H₂₁FN₂S, the mean planes of the benzene ring and the thio­urea fragment form a dihedral angle of 61.93 (9)°. In the crystal, pairs of weak N—H...S inter­actions link the mol­ecules, forming inversion dimers.

6-Methyl-1-({[(2E)-2-methyl-3-phenyl­prop-2-en-1-yl]­oxy}meth­yl)-1,2,3,4-tetra­hydro­quinazoline-2,4-dione

In the title compound, C₂₀H₂₀N₂O₃, the ten atoms comprising the quinazoline ring are essentially planar (r.m.s. deviation = 0.024 Å), and this plane is almost orthogonal to the terminal phenyl ring [dihedral angle = 82.87 (7)°]. The conformation about the ethyl­ene bond [1.335 (2) Å] is E and there is a significant twist between this residue and the adjacent phenyl ring [C—C—C— torsion angle = −48.4 (3)°]. The crystal structure features centrosymmetric dimeric units linked by pairs of N—H...O hydrogen bonds between the amide groups which lead to eight-membered {...HNCO}₂ synthons. These are consolidated into a three-dimensional architecture by C—H...O, C—H...π and π–π inter­actions [centroid–centroid distances = 3.5087 (8) and 3.5645 (9) Å].

6-Chloro-1-({[(2E)-2-methyl-3-phenyl­prop-2-en-1-yl]­oxy}meth­yl)-1,2,3,4-tetra­hydro­quinazoline-2,4-dione

In the title compound, C₁₉H₁₇ClN₂O₃, the conformation about the ethyl­ene bond [1.333 (2) Å] is E. The ten atoms comprising the quinazoline ring are essentially planar (r.m.s. deviation = 0.032 Å) and their mean plane forms a dihedral angle of 13.89 (7)° with the terminal phenyl ring; the mol­ecule has an open conformation as these substituents are directed away from each other. In the crystal, centrosymmetrically related mol­ecules are connected via N—H...O hydrogen bonds between the amide groups, leading to eight-membered {...HNCO}₂ synthons. These are consolidated into a three-dimensional architecture by C—H...O, C—H...π and π–π inter­actions [ring centroid(N₂C₄)...centroid(C₆) distance = 3.5820 (11) Å].

5-Meth­oxy-2-[(5-meth­oxy-1H-indol-1-yl)carbon­yl]-1H-indole

The asymmetric unit of the title compound, C₁₉H₁₆N₂O₃, comprises three independent mol­ecules (A, B and C). The inversion-related molecule of A is virtually superimposable upon the other two molecules. In each mol­ecule, there is a twist in the link between the approximately syn carbonyl and amine groups [the N—C—C—O torsion angles range from 19.73 (19) to −21.2 (2)°]. Each mol­ecule has a bent shape quanti­fied in terms of the dihedral angle between the indole and indole fused-ring systems [range = 45.69 (5)–47.91 (5)°]. In the crystal, the A and B mol­ecules form dimeric aggregates via ten-membered {...HNC₂O}₂ synthons, while the C mol­ecules self-associate similarly but about a centre of inversion.

2-[(Cyclo­hex-3-en-1-ylmeth­oxy)meth­yl]-6-phenyl-1,2,4-triazine-3,5(2H,4H)-dione

In the title 1,2,4-triazine derivative, C₁₇H₁₉N₃O₃, the heterocyclic ring is planar (r.m.s. deviation = 0.040 Å) and effectively coplanar with the adjacent phenyl ring [dihedral angle = 4.5 (2)°] but almost perpendicular to the (cyclo­hex-3-en-1-ylmeth­oxy)methyl residue [N—N—C—O torsion angle = 71.6 (5)°], so that the mol­ecule has an `L' shape. Supra­molecular chains along [001] are formed in the crystal via N—H...O hydrogen bonds where the acceptor O atom is the ether O atom. The adjacent carbonyl O atom forms a complementary C—H...O contact resulting in the formation of a seven-membered {...HNCO...HCO} heterosynthon; the second carbonyl O atom forms an intra­molecular C—H...O contact. Chains are connected into a supra­molecular layer in the ac plane by π–π inter­actions [ring centroid–centroid distance = 3.488 (3) Å]. The central atom in the –CH₂CH₂C(H)= residue of the cyclo­hexene ring is disordered over two sites, with the major component having a site-occupancy factor of 0.51 (2).

1-{(E)-[3-(1H-Imidazol-1-yl)-1-(4-meth­oxy­phen­yl)propyl­idene]amino}-3-(2-methyl­phen­yl)urea

In the title compound, C₂₁H₂₃N₅O₂, the conformation about the imine bond [1.287 (3) Å] is E. Overall, the mol­ecule has a disk shape, the dihedral angles between the imidazole ring and the meth­oxy­phenyl and methyl­phenyl rings being 49.42 (13) and 42.62 (13)°, respectively; the dihedral angle between the benzene rings is 20.11 (11)°. In the urea moiety, the N—H atoms are anti to each other and one of these forms an intra­molecular N—H...N hydrogen bond. In the crystal, centrosymmetric dimers are formed via N—H...N(imidazole) hydrogen bonds, which are connected into a three-dimensional architecture by C—H...O(carbon­yl) and (methyl­ene)C—H...π inter­actions. The crystal studied was a non-merohedral twin with a minor component of 48.3 (1)%.

1-{(E)-[3-(1H-Imidazol-1-yl)-1-phenyl­propyl­idene]amino}-3-(2-methyl­phen­yl)urea

In the title compound, C₂₀H₂₁N₅O, the conformation about the imine bond [1.289 (3) Å] is E. Overall, the mol­ecule is disk-shaped with the imidazole ring located above the remainder of the mol­ecule and with the dihedral angles of 10.97 (15) and 12.11 (15)°, respectively, between the imidazole ring and the phenyl and methyl­benzene rings; the dihedral angle between the aromatic rings is 8.17 (14)°. Within the urea unit, the N—H atoms are anti to each other and one of the N—H atoms forms an intra­molecular N—H...N hydrogen bond. Helical supra­molecular chains along [001] are formed via N—H...N(imidazole) hydrogen bonds in the crystal structure. These are connected into a three-dimensional architecture by C—H...O(carbon­yl) and C—H...π inter­actions.

1-{[(2,3-Dihydro-1H-inden-2-yl)­oxy]meth­yl}quinazoline-2,4(1H,3H)-dione

In the title mol­ecule, C₁₈H₁₆N₂O₃, the five-membered ring has an envelope conformation, with the substituted C atom deviating by 0.342 (4) Å from the mean plane P calculated for the remainder of the non-H atoms of the 2,3-dihydro-1H-indene fragment. The mean planes of quinazoline-2,4(1H,3H)-dione fragment and P form a dihedral angle of 59.08 (4)°. In the crystal, pairs of N—H...O hydrogen bonds link mol­ecules into inversion dimers, and weak C—H...O hydrogen bonds and π–π inter­actions between the benzene rings of the quinazoline ring systems [centroid–centroid distance = 3.538 (3) Å] further consolidate the packing.

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

The imine residue [C=N = 1.268 (3) Å; conformation = E] is twisted [N—N—C—N = 87.8 (2)°] out of the plane (r.m.s. deviation = 0.016 Å) of the central 1,2,4-triazole ring in the title compound, C₃₀H₃₄F₂N₆S. A small twist also occurs between the imine and terminal benzene rings [N—C—C—C = −169.8 (2)°]. The piperazine ring (chair conformation) occupies a position almost normal to the central plane [N—N—C—N = 87.8 (2)°]. In the crystal, the mol­ecules are consolidated into a three-dimensional architecture via C—H...S, C—H...π and π–π inter­actions, the latter between centrosymmetrically related difluoro­benzene rings [inter-centroid distance = 3.9389 (18) Å].

2-Benzyl­sulfanyl-4-[(4-methyl­phen­yl)sulfan­yl]-6-pentyl­pyrimidine-5-carbonitrile

In the title compound, C₂₄H₂₅N₃S₂, the S-bound benzene rings have orthogonal [dihedral angle = 85.31 (9)°] and splayed [67.92 (11)°] orientations with respect to the pyrimidine ring; the dihedral angle between the benzene rings is 48.18 (12)°. The pentyl group has an extended all-trans conformation and lies to one side of the pyrimidine ring [the N_py-C_py-C_p-C_p torsion angle = -85.7 (2)°; py = pyrimidine and p = pent­yl].

2-[(4-Chloro­benz­yl)sulfanyl]-4-(2-methyl­prop­yl)-6-[3-(trifluoro­meth­yl)anilino]­pyrimidine-5-carbonitrile

Three independent mol­ecules comprise the asymmetric unit of the title compound, C₂₃H₂₀ClF₃N₄S. The conformations of the mol­ecules are similar with the chloro­benzene and CF₃-benzene rings almost perpendicular to, and almost co-planar with, the pyrimidinyl ring [range of dihedral angles = 80.36 (13)–88.07 (14) and 11.89 (14)–23.30 (14)°, respectively]; the benzene rings are roughly orthogonal to each other [64.81 (16)–72.16 (15)°]. In the crystal, two of the independent mol­ecules associate via weak N—H...N(cyano) hydrogen bonds and 12-membered {...HNC₃N}₂ synthons; the third independent mol­ecule self-associates similarly but about a centre of inversion. The sample studied was found to be a non-merohedral twin and the minor twin component refined to 47.16 (7)%.

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

The mol­ecule of the title compound, C₂₄H₃₂N₄OS, is a functionalized 1,3,4-oxadiazole-2-thione with substituted piperazine and adamantanyl substituents attached at the 3- and 5-positions, respectively, of the oxadiazole spacer with an approximately C-shaped conformation. In the crystal, mol­ecules form dimers via C—H...S inter­action. The piperazine ring has a chair conformation; the substituents S, methyl­ene C and adamantane C of the essentially planar oxadiazole ring are approximately in the same plane, with distances of −0.046 (2), −0.085 (5) and 0.003 (4) Å, respectively. The dihedral angle between the planes of the phenyl and oxadiazole rings is 31.3 (3)°.

N′-(Adamantan-2-yl­idene)benzo­hydrazide

The title mol­ecule, C₁₇H₂₀N₂O, is a functionalized hydrazine with benzoyl and adamantyl substituents attached to the two hydrazine N atoms. In the crystal, mol­ecules are linked via N—H...N hydrogen bonds, forming chains propagating along the a-axis direction. There are also C—H...O, C—H...N and C—H...π inter­actions present within the chains.