In the title compound, C11H15ClN6O4S, which belongs to the neonicotinoid class of insecticidally active heterocyclic compounds, the six-membered triazine ring adopts an opened envolope conformation. The planar nitro imine group [dihedral angle between nitro and imine groups = 1.07 (7)°] and the thiazole ring are oriented at a dihedral angle of 69.62 (8)°. A classical intramolecular N—H⋯O hydrogen bond is found in the molecular structure. Moreover, one classical intermolecular N—H⋯N and four non-classical C—H⋯O and C—H⋯N hydrogen bonds are also present in the crystal structure. Besides intermolecular hydrogen bonds, the Cl atom forms an intermolecular short contact [3.020 (2) Å] with one of the nitro O atoms.
2,25-Dioxo-27,28-diphenyl-30-oxa-29-thia-3,10,17,24-tetraazapentacyclo[188.8.131.52,15.04,9.018,23]triaconta-5,7,9(4),10,12,14,16,18,20,22,26,28-dodecaene chloroform disolvate
The macrocycle of the title compound, C36H24N4O3S·2CHCl3, contains a rigid framework with the nitrogen and oxygen heteroatoms pointing in towards the center of the macrocyclic cavity. The macrocycle is essentially planar (r.m.s. deviation = 0.027 Å) except for the thiophene ring. The dihedral angle between the thiophene ring plane and the mean plane of the central macrocyclic core including all atoms except sulfur is 21.6 (1)°. Four intramolecular hydrogen bonds occur: two are between the amide hydrogen atoms and the Schiff base nitrogen atoms, while the others are between the amide hydrogen atoms and the sulfur atom of the thiophene. The two solvate chloroform molecules are bound to the carbonyl oxygen atoms of the ligand by weak C—H⋯O hydrogen bonding. In addition, the structure reveals intermolecular Cl⋯Cl close contacts [3.308 (2), 3.404 (2) and 3.280 (2) Å] between the chloroform solvate molecules. In the crystal, the macrocycles form layers parallel to (101), with an interlayer distance of 3.362 (3) Å. This short distance is determined by the stacking interactions between the amide carbonyl and imine fragments of neighboring ligands.
In the molecule of the title compound, C12H11ClN4O4, the pyrazole ring is coplanar with the amino and ethoxycarbonyl groups within 0.026 (2) and 0.105 (2) Å, respectively. The C
6 ring of the 4-chloro-2-nitrophenyl group is twisted by 53.58 (4)° relative to the plane of the pyrazole ring. The planar structure of the pyrazole ring is stabilized by an intramolecular N—H⋯O hydrogen bond between its substituents. Neighbouring molecules are linked through intermolecular N—H⋯N and N—H⋯O hydrogen bonds, giving rise to one-dimensional tapes along the b axis. Molecules in the chain are linked to those of an adjacent chain through weak C—H⋯O interactions, forming a three-dimensional network.
In the title compound, C25H15ClN2O6S, the carbazole ring system is essentially planar, with a maximum deviation of 0.152 (3) Å for the C atom to which the 4-chloro-2-nitrophenyl ring is attached. Its mean plane is almost orthogonal to the phenylsulfonyl and nitrophenyl rings, making dihedral angles of 82.64 (14) and 79.89 (13)°, respectively. The N atom of the nitro group deviates by 0.032 (3) Å from the benzene ring to which it is attached. The molecular structure features intramolecular O—H⋯O and C—H⋯O hydrogen bonds, which generate three S(6) ring motifs. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, which generate C(6) and C(9) chains running in the  and  directions, respectively, forming a two-dimensional network lying parallel to (001). There are also R
3(28) supramolecular graph-set ring motifs enclosed within these networks.
With the exception of the C atoms of two of the methyl groups of the tert-butyl substituent, all of the non-H atoms of the title compound, C12H14ClN3O3S, lie on a mirror plane. The 2-chloro-5-nitrophenyl and 2,2-dimethylpropionyl substituents are, respectively, cis and trans relative to the thiocarbonyl S atom across the two C—N bonds. Intramolecular N—H⋯O and C—H⋯S hydrogen bonds form S(6) ring motifs, also in the mirror plane. Despite the presence of two N—H subsituents, no intermolecular hydrogen bonds are observed in the crystal structure. Weak π–π contacts [centroid–centroid distances of 4.2903 (17) Å] involving adjacent aromatic rings link the molecules in a head-to-tail fashion above and below the molecular plane.
In the title compound, C13H10ClN3O3, prepared by the reaction of 1-chloro-3-isocyanatobenzene with 4-nitrobenzenamine, the two substituent benzene rings are roughly coplanar [inter-ring dihedral angle = 8.70 (7)°]. In the crystal, molecules make cyclic intermolecular associations through two urea–nitro N—H⋯O hydrogen bonds, forming a chain structure [give chain direction] in which there are also weak intermolecular C—H⋯Cl interactions. The urea O atom has only intramolecular aromatic ring C—H⋯O associations.
The molecule of the title compound, C20H19ClN4O4S, features a central pyrazole ring that possesses a benzene substituent, as well as a conjugated =C—C=C—Cmethyl substituent. The benzene ring is slightly twisted [dihedral angle = 7.7 (2)°] with respect to the five-membered ring; the mean plane of the zigzag =C—C=C—C fragment [torsion angle = 178.0 (4)°] is also slightly twisted [dihedral angle = 10.6 (4)°]. The amine and hydroxy groups form intramolecular hydrogen bonds. The amide group uses one of its H atoms to form a hydrogen bond to the sulfamyl O atom of an inversion-related molecule. Adjacent dimers are further linked by an N—Hamido⋯Npyrazole hydrogen bond to generate a linear chain. The crystal studied is a nonmerohedral twin with a minor twin component of 25.6 (2)%.
The title molecule, C14H11ClN4O4, is in an E configuration and is twisted with the dihedral angle between the two benzene rings being 38.48 (8)°. The ethylidenehydrazine plane makes dihedral angles of 6.03 (10) and 44.04 (11)°, respectively, with the dinitro- and chloro-substituted benzene rings. The two nitro groups are essentially coplanar with the bound benzene ring, making dihedral angles of 0.9 (2) and 1.65 (18)°. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked by a weak C—H⋯O interaction into a chain along the c axis. The chains are further stacked along the b axis by a π–π interaction with a centroid–centroid distance of 3.6088 (10) Å.
The dihedral angle between the benzene and pyridyl rings in the title compound, C11H8ClN3O2, is 22.65 (10)°, indicating a twisted molecule. The amine H and nitro O atoms form a donor–acceptor pair for an intramolecular N—H⋯O hydrogen bond so that the nitro group is almost coplanar with the pyridine ring to which it is connected [O—N—C—C torsion angle = 7.4 (3)°]. The pyridine N and Cl atoms are approximately syn. The crystal packing features C—H⋯Cl interactions that lead to undulating supramolecular chains along . These are connected into sheets by π–π interactions occurring between the benzene rings and between the pyridine rings of translationally related molecules along the b axis [centroid–centroid distances = length of b axis = 3.7157 (2) Å].
In the title compound, C21H14ClN3O5, an intramolecular C—H⋯O hydrogen bond generates an S(7) ring motif and the furan and pyrazole rings are almost coplanar, making a dihedral angle of 1.98 (5)°. The pyrazole ring is inclined at dihedral angles of 47.59 (4) and 7.27 (4)° to the chlorophenyl and methoxyphenyl groups, respectively. The nitro group is almost coplanar to its attached furan ring [dihedral angle = 2.03 (12)°]. In the crystal, intermolecular C—H⋯O hydrogen bonds link the molecules into a three-dimensional network. The crystal structure also features short intermolecular O⋯N [2.8546 (12) Å] and Cl⋯O [3.0844 (9) Å] contacts as well as aromatic π–π stacking interactions [centroid–centroid distance = 3.4367 (6) Å].
The amide group in the title compound, C7H6ClN3O3, is significantly twisted out of the plane of the benzene ring [C—C—C—O = 34.2 (5)°] whereas the nitro group is almost co-planar [O—N—C—C = 4.0 (5)°] with the ring. Intramolecular N—H⋯O and N—H⋯Cl hydrogen bonds occur. In the crystal, the molecules are linked by N—H⋯O hydrogen bonds, generating layers propagating in the ab plane.
In the title compound, [Sn(C6H5)3(C7H3ClNO4)], the four-coordinate SnIV atom exists in a distorted tetrahedral geometry, formed by a monodentate carboxylate group and three phenyl rings. The conformation is stabilized by an intramolecular C—H⋯O hydrogen bond, which generates an S(5) ring. The aromatic ring of the 4-chloro-3-nitrobenzoate ligand makes dihedral angles of 75.64 (12), 64.37 (12) and 2.97 (12)° with the three phenyl ligands. The O atoms of the nitro group are disordered over two sets of sites in a 0.817 (5):0.183 (5) ratio. In the crystal, molecules are linked via intermolecular C—H⋯O hydrogen bonds into chains running parallel to .
In the title compound, C25H16Cl2O4·C2H6O, the two 4-chlorobenzoyl groups are in syn orientations with respect to the naphthalene ring system and are approximately parallel to each other: the dihedral angle between the benzene rings is 11.43 (16)°. The conformation around each of the carbonyl C—(C=O)—C groups forms a larger angle to the plane of the naphthalene ring system than that to the benzene ring; the angles of the C=O bond vector with the naphthalene ring system and the benzene ring are 55.4 (3) versus 13.5 (3)° and 52.2 (3) versus 17.9 (3)°. An intramolecular O—H⋯O=C hydrogen bond generates a six-membered ring. In the crystal structure, intermolecular O—H⋯O hydrogen bonds including the ethanol solvent molecule are observed. A C—H⋯O interaction also occurs. The ethyl group of the ethanol molecule is disordered over two positions with site occupancies of 0.63 and 0.37. The crystal studied was an inversion twin.
The benzene rings of the biphenyl group in the title compound, C20H14ClN3O3S, are nearly coplanar [maximum deviation = 0.20 (3) Å]. The mean plane of the biphenyl group forms a dihedral angle of 5.24 (7)° with the aromatic ring of the nitrochlorobenzene group. Intramolecular N—H⋯Cl, N—H⋯O and C—H⋯S hydrogen bonds stabilize the cis–trans conformation of the molecule. In the crystal, molecules are linked by C—H⋯O and C—H⋯S hydrogen bonds into mutually interwoven corrugated layers parallel to (10-2).
In the title compound, C18H19ClN4O3, the dihydropyrimidinone ring adopts a flattened boat conformation. The dihedral angle between the phenyl and pyrazole rings is 43.39 (6)°. An intramolecular C—H⋯O contact generates an S(8) ring motif that stabilizes the molecular conformation and precludes the carbonyl O atom of the ester group from forming intermolecular interactions. Molecules are linked into centrosymmetric dimers by pairs of N—H⋯O hydrogen bonds and the dimers are linked into infinite chains along  by N—H⋯N hydrogen bonds.
There are two crystallographically independent molecules in the asymmetric unit of the title compound, C14H11ClN4O4, with the same E conformation about the C=N double bond. The molecules are approximately planar, with a dihedral angle between the benzene rings of 10.24 (12)° in one molecule and 4.73 (12)° in the other. In both molecules, the ortho-nitro groups of the 2,4-dinitrophenyl units are coplanar to their bound benzene rings, whereas the para-nitro groups are slightly twisted. In each molecule, intramolecular N—H⋯O hydrogen bonds generate S(6) ring motifs. In the crystal, molecules are linked by weak C—H⋯O interactions into sheets parallel to the (-102) plane. These sheets are stacked by π–π interactions, with centroid–centroid distances of 3.7008 (14) and 3.7459 (14) Å. A Cl⋯O short contact [3.111 (2) Å] is observed.
The asymmetric unit of the title salt, C5H6ClN2
+·C7H5O6S−, contains two independent 2-amino-5-chloropyridinium cations and two independent 3-carboxy-4-hydroxybenzenesulfonate anions. In both anions, the O atoms of the sulfonate group are disordered over two sets of positions, with occupancy ratios of 0.47 (5):0.53 (5) and 0.50 (8):0.50 (8). In each anion, an intramolecular O—H⋯O hydrogen bond generating an S(6) motif is observed. In the crystal structure, the cations and anions are linked via N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds, forming a two-dimensional network parallel to (110). The structure is further stabilized by π–π interactions between cations and anions [centroid–centroid distance = 3.5454 (12) Å]. The crystal studied was a non-merohedral twin, with a ratio of the twin components of 0.715 (3):0.285 (3).
In the title compound, C20H15ClN2OS, the benzene rings of the biphenyl group are at an angle of 44.23 (12)°. The C4N2OS central thiourea fragment makes dihedral angles with the benzene carbonyl and chlorobenzene rings of 55.96 (9) and 64.09 (9)°, respectively. The trans–cis geometry of the thiourea group is stabilized by the intramolecular hydrogen bond between the carbonyl O atom and the H atom of the cis-thioamide. In the crystal structure, molecules are linked by N—H⋯S and N—H⋯O intermolecular hydrogen bonds to form one-dimensional chains along the c axis. C—H⋯π interactions also contribute to the stability of the molecule.
In the title compound, C11H14N2O5, the molecular structure is stabilized by an intramolecular N—H⋯O hydrogen bond, which generates an S(6) ring motif. The nitro group is twisted slightly from the attached benzene ring, forming a dihedral angle of 5.2 (2)°. In the crystal packing, intermolecular O—H⋯O and C—H⋯O hydrogen bonds link the molecules into a three-dimensional network. The crystal studied was a non-merohedral twin, the refined ratio of the twin components being 0.264 (2):0.736 (2).
In the title compound, C11H12N2O5, the conformation of the N—H bond in the amide segment is syn to the ortho-nitro group in the benzene ring. The amide C=O and the carboxyl C=O of the acid segment are syn to each other and both are anti to the H atoms on the adjacent –CH2 groups. Furthermore, the C=O and O—H bonds of the acid group are in syn positions with respect to each other. The dihedral angle between the benzene ring and the amide group is 36.1 (1)°. The amide H atom shows bifurcated intramolecular hydrogen bonding with an O atom of the ortho-nitro group and an intermolecular hydrogen bond with the carbonyl O atom of another molecule. In the crystal, the N—H⋯O(C) hydrogen bonds generate a chain running along the  direction. Inversion dimers are formed via a pair of O—H⋯O(C) interactions, that form an eight-membered hydrogen-bonded ring involving the carboxyl group.
The title molecule, C10H8ClN3O7, is twisted with the dihedral angle between the amide and benzene ring being 38.75 (11)°. The C—N—C—C torsion angle between the amide and acetyl groups is −150.1 (2)°. Finally, each nitro group is twisted out of the plane of the benzene ring to which it is connected [O—N—C—C torsion angles = 34.0 (3) and −64.5 (3)°]. Linear supramolecular chains along  and mediated by N—H⋯O hydrogen bonds between successive amide groups dominate the crystal packing. The chains are consolidated into the three-dimensional structure by C—H⋯O contacts.
The title compound, C12H9ClN2OS2, exists in the thioamide form with an intramolecular N—H⋯O hydrogen bond across the thiourea and the carbonyl group. The dihedral angle between the rings is 10.36 (11)°. In the crystal structure, molecules are linked into chains by weak intermolecular C—H⋯Cl hydrogen-bonding interactions.
The six-membered N-heterocyclic ring of title compound, C17H17ClN2O, is fused with a methyl-substituted cyclohexene ring. The nitrogen-bearing ring has an envelope conformation with the benzene ring-bearing C atom lying 0.432 (6) Å out of the plane defined by the other five atoms (r.m.s. deviation 0.011 Å); its benzene substituent is aligned at 84.7 (1)° to the latter plane. The cyclohexene ring adopts a half-chair conformation. In the crystal, two molecules are linked about a center of inversion by pairs of N–H⋯O hydrogen bonds, generating dimers. An ethylene portion is disordered over two orientations in a 1:1 ratio. The crystal studied was a non-merohedral twin with a 15.3 (1)% minor component.
In the title compound, C16H14N2O5, a non-merohedral twin, the dihedral angle between the mean planes of the two benzene rings is 4.0 (9)°. The ethyl group is disordered [0.643 (14) and 0.357 (14) occupancy]. The nitro group is twisted by 16.4 (4)° from the mean plane of the benzene ring and the mean plane of the carbonyl group is twisted from the mean planes of the two benzene rings by 4.5 (0) and 4.7 (9)°. An intramolecular N—H⋯O hydrogen bond occurs. The crystal packing is stabilized by weak intermolecular C—H⋯O hydrogen-bond interactions.
In the title molecule, C7H8ClN3O, the pyrazine and amide groups are almost co-planar [N—C—C—N torsion angle = −2.4 (2) °], a conformation stabilized by an intramolecular N—H⋯N hydrogen bond. The chloroethyl group lies out of the plane [N—C—C—Cl = −65.06 (17) °]. In the crystal, the presence of N—H⋯N hydrogen bonds leads to the formation of a C(6) supramolecular chain along the b axis. The carbonyl-O atom accepts two C—H⋯O interactions. These, plus Cl⋯Cl short contacts [3.3653 (6) Å], consolidate the packing of the chains in the crystal.