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In the title compound, C22H26N4OS, the benzene rings of the (2-methylpropyl)phenyl and 4-methoxyphenyl units form dihedral angles of 66.85 (3) and 25.96 (3)°, respectively, with the triazole ring. The dihedral angle between the two benzene rings is 87.42 (2)°. The –CH(CH3) linkage is disordered over two orientations with occupancies of 0.907 (3) and 0.093 (3). An intramolecular C—H⋯S hydrogen bond generates an S(6) ring motif. Intermolecular N—H⋯S hydrogen bonds and C—H⋯π interactions are observed.
doi:10.1107/S1600536809014949
PMCID: PMC2977816
PMID: 21583953
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.
doi:10.1107/S1600536810040201
PMCID: PMC3009072
PMID: 21589003
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.
doi:10.1107/S160053681105001X
PMCID: PMC3239123
PMID: 22199971
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.
doi:10.1107/S1600536810018878
PMCID: PMC2979404
PMID: 21579526
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].
doi:10.1107/S1600536810011931
PMCID: PMC2979246
PMID: 21579120
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.
doi:10.1107/S1600536809000488
PMCID: PMC2968147
PMID: 21581889
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 [101]. 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].
doi:10.1107/S1600536811044011
PMCID: PMC3247465
PMID: 22220083
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.
doi:10.1107/S1600536812009142
PMCID: PMC3343961
PMID: 22590042
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).
doi:10.1107/S1600536810008147
PMCID: PMC2983846
PMID: 21580671
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.
doi:10.1107/S1600536809024672
PMCID: PMC2977335
PMID: 21583450
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).
doi:10.1107/S1600536812016686
PMCID: PMC3344595
PMID: 22590357
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 [101] by N—H⋯N hydrogen bonds.
doi:10.1107/S1600536809016365
PMCID: PMC2969568
PMID: 21583097
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.
doi:10.1107/S160053681200548X
PMCID: PMC3295481
PMID: 22412592
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.
doi:10.1107/S1600536811002236
PMCID: PMC3051796
PMID: 21523125
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 [010] 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.
doi:10.1107/S1600536811050446
PMCID: PMC3239110
PMID: 22199958
In the title compound, C17H15N3O5S, the nitro and thioureido groups are twisted by 7.2 (7) and 21.4 (2)°, respectively, from the nitrobenzene ring plane whereas the thioureido and the ethyl ester group make dihedral angles of 43.0 (1) and 18.0 (2)°, respectively, with the benzene rings to which they are attached. Intramolecular N—H⋯O hydrogen-bonding interactions are observed. In the crystal, intermolecular N—H⋯O hydrogen bonds connect the molecules into chains running along the a axis.
doi:10.1107/S1600536810011116
PMCID: PMC2984025
PMID: 21580777
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.
doi:10.1107/S1600536807062265
PMCID: PMC2915178
PMID: 21200669
In the title compound, C12H9NOS, the sulfoxide O atom is disordered over two sites with occupancies of 0.907 (4) and 0.093 (4). The dihedral angle betweeen the two aromatic rings is 18.40 (14)°. Different types of supramolecular interactions including intermolecular N—H⋯O hydrogen bonds and π–π contacts [centroid–centroid distances = 3.9096 (16) and 4.1423 (16) Å] between the aromatic rings of symmetry-related molecules are observed in the crystal structure.
doi:10.1107/S1600536810047914
PMCID: PMC3011726
PMID: 21589550
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.
doi:10.1107/S1600536810041656
PMCID: PMC3009184
PMID: 21589067
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.
doi:10.1107/S1600536810013863
PMCID: PMC2979166
PMID: 21579205
In the molecule of the title compound, C10H7ClN2O5, the acyclic C=C double bond is cis configured. The C=O and O—H bonds of the acid group are in a relatively rare anti position to each other, due to the donation of intramolecular hydrogen bond to the amide by the carboxyl group. The nitro group is significantly twisted [dihedral angle = 66.9 (3)°] out of the plane of the remaining atoms, which are almost coplanar (r.m.s. deviation for non-H atoms except the nitro group = 0.202 Å). In the crystal, N—H⋯O hydrogen bonds link the molecules into zigzag chains running along the b axis.
doi:10.1107/S1600536812008021
PMCID: PMC3297923
PMID: 22412726
The title compound, C12H12Cl2N2O3, crystallizes as a non-merohedral twin with a twinning ratio of 0.51:0.49. The molecule adopts a keto–hydrazo tautomeric form stabilized by an intramolecular N—H⋯O hydrogen bond. The configuration around the N—N bond is trans.
doi:10.1107/S1600536807065300
PMCID: PMC2960280
PMID: 21201455
In the title compound, C16H14ClFO3, the dihedral angle between the mean planes of the two benzene rings is 71.50 (5)°. Due to an intramolecular O—H⋯O hydrogen bond between the hydroxy group and the carbonyl O atom of the ethyl ester group, the ethyl ester group lies within the ring plane. The crystal structure is consolidated by intermolecular C—H⋯O and C—H⋯F interactions.
doi:10.1107/S160053681103217X
PMCID: PMC3200854
PMID: 22058957
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 [100] 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.
doi:10.1107/S1600536812007258
PMCID: PMC3297880
PMID: 22412683
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 [010].
doi:10.1107/S160053681103282X
PMCID: PMC3200665
PMID: 22065496