The asymmetric unit of the title compound, C21H23ClN4S, contains nine crystallographically independent molecules, labelled A to I. The orientation of the 2-[4-(2-methylpropyl)phenyl]ethyl unit with respect to the rest of the molecule is significantly different in molecules E, F, H and I compared to the other independent molecules. The isobutyl group of molecule B is disordered over two orientations, with occupancies of 0.764 (7) and 0.236 (7). The benzene rings of the chlorophenyl and methylpropylphenyl units form dihedral angles of 21.90 (11) and 71.47 (11)°, respectively, with the triazole ring in molecule A [9.15 (11) and 80.37 (11)° in B, 7.14 (11) and 84.06 (11)° in C, 25.76 (11) and 76.59 (11)° in D, 13.68 (11) and 76.82 (10)° in E, 8.38 (11) and 69.77 (10)° in F, 30.34 (11) and 78.12 (11)° in G, 21.20 (11) and 71.58 (10)° in H, and 27.65 (11) and 65.23 (11)° in I]. In each independent molecule, a C—H⋯S hydrogen bond is observed. The crystal packing is stabilized by N—H⋯S and C—H⋯S hydrogen bonds, and by C—H⋯π interactions involving the methylpropylphenyl ring.
The title compounds are iron(II) dihalide complexes of the bulky arylimidazole ligand 1-(2,6-diisopropylphenyl)-1H-imidazole. The FeCl2 and FeBr2 complexes are isotypic, while the third compound, also an FeBr2 complex, crystallizes as a diethyl ether disolvate.
The title compounds, [FeCl2(C15H20N2)4], (I), [FeBr2(C15H20N2)4], (II), and [FeBr2(C15H20N2)4]·2C4H10O, (IIb), respectively, all have triclinic symmetry, with (I) and (II) being isotypic. The FeII atoms in each of the structures are located on an inversion center. They have octahedral FeX
2N4 (X = Cl and Br, respectively) coordination spheres with the FeII atom coordinated by two halide ions in a trans arrangement and by the tertiary N atom of four arylimidazole ligands [1-(2,6-diisopropylphenyl)-1H-imidazole] in the equatorial plane. In the two independent ligands, the benzene and imidazole rings are almost normal to one another, with dihedral angles of 88.19 (15) and 79.26 (14)° in (I), 87.0 (3) and 79.2 (3)° in (II), and 84.71 (11) and 80.58 (13)° in (IIb). The imidazole rings of the two independent ligand molecules are inclined to one another by 70.04 (15), 69.3 (3) and 61.55 (12)° in (I), (II) and (IIb), respectively, while the benzene rings are inclined to one another by 82.83 (13), 83.0 (2) and 88.16 (12)°, respectively. The various dihedral angles involving (IIb) differ slightly from those in (I) and (II), probably due to the close proximity of the diethyl ether solvent molecule. There are a number of C—H⋯halide hydrogen bonds in each molecule involving the CH groups of the imidazole units. In the structures of compounds (I) and (II), molecules are linked via pairs of C—H⋯halogen hydrogen bonds, forming chains along the a axis that enclose R
2(12) ring motifs. The chains are linked by C—H⋯π interactions, forming sheets parallel to (001). In the structure of compound (IIb), molecules are linked via pairs of C—H⋯halogen hydrogen bonds, forming chains along the b axis, and the diethyl ether solvent molecules are attached to the chains via C—H⋯O hydrogen bonds. The chains are linked by C—H⋯π interactions, forming sheets parallel to (001). In (I) and (II), the methyl groups of an isopropyl group are disordered over two positions [occupancy ratio = 0.727 (13):0.273 (13) and 0.5:0.5, respectively]. In (IIb), one of the ethyl groups of the diethyl ether solvent molecule is disordered over two positions (occupancy ratio = 0.5:0.5).
arylimidazole; iron(II); crystal structure
The asymmetric unit of the 1:4 title co-crystal of 2-amino-4-(4-chlorophenyl)-5,6-dihydrobenzo[h]quinoline-3-carbonitrile and 3-amino-1-(4-chlorophenyl)-9,10-dihydrophenanthrene-2,4-dicarbonitrile, 0.2C20H14ClN3·0.8C22H14ClN3, has the atoms of the fused-ring system and those of the amino, cyano and chlorophenyl substitutents overlapped. The fused-ring system is buckled owing to the ethylene linkage in the central ring. There are two independent overlapped molecules in the asymmetric unit. In one independent molecule, the two flanking aromatic rings are twisted by 24.4 (1)° and the ring of the chlorophenyl substituent is twisted by 87.3 (1)° relative to the amino- and cyano-bearing aromatic ring. In the second molecule, the respective dihedral angles are 26.1 (1) and 57.8 (1)°. The two independent molecules are linked by N—H⋯N hydrogen bonds into dimers.
The title compound, C24H19ClN2, crystallizes with two independent molecules in the asymmetric unit. The prop-2-enyl substituents on the imidazole rings adopt similar conformations in the two molecules. The 4-and 5-substituted phenyl rings and the benzene ring make dihedral angles of 67.06 (8), 5.61 (8) and 41.09 (8)°, respectively, with the imadazole ring in one molecule and 71.53 (8), 28.85 (8) and 41.87 (8)°, respectively, in the other. The crystal structure features C—H⋯π interactions and weak π–π stacking interactions [centroid–centroid distances = 3.6937 (10) and 4.0232 (10) Å] between the chlorophenyl rings, which form a three-dimensional supramolecular structure.
The title compound, C15H12ClNO, a substituted chalcone, adopts an E configuration with respect to the C=C bond of the enone unit. The molecule is not planar, as can be seen from the dihedral angle of 28.9 (2)° between the two rings which are twisted from each other. The enone segment of the molecule is not coplanar with the chlorophenyl ring, making a dihedral angle of 23.4 (3)° with it. The amino group is also not coplanar with the ring to which it is bound, making a dihedral angle of 35 (4)°. In the crystal structure, adjacent molecules are linked by N—H⋯O interactions into one-dimensional infinite chains along the c axis, and are further stacked as one-dimensional zigzag chains down the b axis, forming two-dimensional extended networks parallel to the bc plane.
There are two molecules in the asymmetric unit of the title imidazole derivative, C20H16ClFN2OS2. In one molecule, the dithiolane ring is disordered over two positions in a 0.849 (9):0.151 (10) ratio. The imidazole ring makes dihedral angles of 79.56 (9) and 18.45 (9)° with the 4-chlorophenyl and 2-fluorophenyl rings, respectively, in one molecule; in the other molecule, the corresponding angles are 82.72 (9) and 17.39 (10)°. In the crystal, molecules are linked by weak C—H⋯O interactions and these linked molecules are stacked along the b axis by π–π interactions with a centroid–centroid distance of 3.4922 (11) Å. In addition, π–π interactions between the imidazole and 2-fluorophenyl rings are also observed, with centroid–centroid distances of 3.4867 (11) and 3.4326 (10) Å. The crystal is further consolidated by weak C—H⋯π interactions. Cl⋯S [3.5185 (8) Å], C⋯O [3.192 (3) Å] and C⋯C [3.326 (2)–3.393 (3) Å] short contacts are also observed.
The asymmetric unit of the title compound, C27H32N4O4·H2O, contains two independent benzimidazole-5-carboxylate molecules and two water molecules. In both main molecules, the pyrrolidine rings are in an envelope conformation with a methylene C atom as the flap. The morpholine rings adopt chair conformations. Both benzimidazole rings are essentially planar, with maximum deviations of 0.008 (1) Å, and form dihedral angles of 37.65 (6) and 45.44 (6)° with the benzene rings. In one molecule, an intramolecular C—H⋯O hydrogen bond forms an S(7) ring motif. In the crystal, O—H⋯O and O—H⋯N hydrogen bonds connect pairs of main molecules and pairs of water molecules into two independent centrosymmetric four-compoment aggregates. These aggregates are connect by C—H⋯O hydrogen bonds leading to the formation of a three-dimensional network, which is stabilized by C—H⋯π interactions.
The asymmetric unit of the title compound, C17H10ClF2N3O, contains three independent molecules. In each molecule, the C=C bond has a cis conformation with respect to the triazole and chlorophenyl groups. The dihedral angles formed by the triazole ring with the diflurophenyl and chlorophenyl benzene rings, respectively, are 20.10 (14) and 73.22 (15), 25.31 (15) and 84.44 (15), and 16.44 (13) and 61.72 (14)° in the three molecules while the dihedral angles between the benzene rings are 66.54 (13), 85.82 (12) and 58.37 (12)°.
In the title compound, C15H10ClNO3, a substituted chalcone, the 2-chlorophenyl and 4-nitrophenyl rings make a dihedral angle of 26.48 (6)°. The nitro group makes a dihedral angle of 11.64 (7)° with the plane of the benzene ring to which it is bound. Weak intramolecular C—H⋯O and C—H⋯Cl interactions involving the enone groups generate S(5) ring motifs, which help to stabilize the planarity of the 3-(2-chlorophenyl)prop-2-en-1-one segment of the molecule. In the crystal structure, adjacent molecules are stacked in a head-to-tail fashion into columns along the a axis by π–π interactions [centroid–centroid distance = 3.6955 (8) Å]. Neighbouring columns are linked by weak C—H⋯O interactions.
The asymmetric unit of the title compound, C24H27N3O4, contains two molecules, A and B. The benzimidazole rings are essentially planar [maximum deviations = 0.0144 (10) and 0.0311 (8) Å in A and B, respectively]. The dihedral angle between the benzimidazole mean plane and its attached benzene ring is 36.90 (5) ° for molecule A and 51.40 (5) ° for molecule B. In both molecules, the pyrrolidine ring adopts an envelope conformation with a C atom as the flap. In molecule B, the flap C atom is disordered over two positions in a 0.711 (6):0.289 (6) ratio. In the crystal, C—H⋯O interactions link the molecules, generating  chains. The crystal packing also features weak π–π interactions between the imidazole and benzene rings [centroid–centroid distances = 3.8007 (7) and 3.8086 (7) Å] and between the benzene rings [centroid–centroid distance = 3.7001 (7) Å] and C—H⋯π interactions involving the benzene rings.
In the title compound, C26H24N2O2, the planar 1H-imidazole ring makes dihedral angles of 35.78 (4), 26.35 (5) and 69.75 (5)°, respectively, with the dimethoxyphenyl ring and the phenyl rings in the 4- and 5-positions. In the crystal, C—H⋯O hydrogen bonds connect neighbouring molecules, forming infinite chains running along the b axis. Furthermore, the crystal structure exhibits a C—H-⋯π interaction between a methyl H atom and a phenyl ring from an adjacent molecule.
In the title compound, [Mn(C10H7N6)2(H2O)4]·2H2O, the complex unit comprises an Mn2+ ion, coordinated by two imidazole N atoms from cis-related monodentate 5-[4-(imidazol-1-yl)phenyl]tetrazolide ligands and four water molecules, together with two water molecules of solvation. The Mn2+ ion lies on a twofold rotation axis and has a slightly distorted octahedral geometry. The molecules are connected by O—H⋯N and O—H⋯O hydrogen bonds involving both coordinated and solvent water molecules, generating a three-dimensional structure. Two C atoms of the imidazole ring of the ligand are each disordered over two sites with occupancy factors of 0.75 and 0.25.
Molecules of two related 1,2-amino alcohols are linked via N—H⋯O=S hydrogen bonds, forming chains along  for the first compound and along  for the second compound.
The title compounds, C22H31NO2S, (1), and C23H33NO2S, (2), are related protected 1,2-amino alcohols. They differ in the substituents on the benzene ring, viz. 2,6-dimethylphenyl in (1) and 2,4,6-trimethylphenyl in (2). The plane of the phenyl ring is inclined to that of the benzene ring by 28.52 (7)° in (1) and by 44.65 (19)° in (2). In the crystal of (1), N—H⋯O=S and C—H⋯O=S hydrogen bonds link molecules, forming chains along , while in (2), similar hydrogen bonds link molecules into chains along . The absolute structures of both compounds were determined by resonance scattering.
crystal structure; sulfinamide; diastereomer; amino alcohol; hydrogen bonding; NMR; column chromatography
The title compound, C26H26N2S2, was synthesized from bis[1,3-bis(3-phenylpropyl)benzimidazolidine-2-ylidene] and CS2 in toluene. The molecular structure is composed of a benzimidazole ring system with two phenylpropyl substituents and a dithiocarboxylate group in the 2-position. The benzimidazole unit is essentially planar, with a maximum atomic deviation of 0.008 (2) Å, and makes dihedral angles of 72.72 (10) and 27.62 (12)°, with the two phenyl rings. The dihedral angle between the two phenyl rings is 55.98 (15)°. The molecular packing is stabilized by a C—H⋯S intermolecular hydrogen-bonding interaction and a C—H⋯π interaction between a benzene H atom and the phenyl ring of a neighbouring molecule.
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 .
The asymmetric unit of the title compound, C21H13ClFNO2S, contains two independent molecules with similar conformations. In the molecules, the thiazole ring is essentially planar [maximum atomic deviations = 0.014 (4) and 0.023 (5) Å] and is oriented with respect to the fluorophenyl ring and chlorophenyl rings at 9.96 (18) and 70.39 (18)° in one molecule and at 7.50 (18) and 68.43 (18)° in the other; the dihedral angles between the fluorophenyl and chlorophenyl rings are 64.9 (2) and 64.6 (2)°, respectively. Intermolecular C—H⋯O and C—H⋯F hydrogen bonds stabilize the three-dimensional supramolecular architecture. Weak C—H⋯π and π–π interactions [centroid–centroid distance = 3.877 (3) Å] lead to a criss-cross molecular packing along the c axis.
In the title salt, C21H21Cl2N2O2
−, the imidazole ring makes dihedral angles of 43.39 (14) and 10.9 (2)° with the 4-methylphenyl and 2,4-dichlorophenyl rings, respectively. The molecule adopts a Z conformation about the C=C double bond, which links the imidazole ring to the 4-methylphenoxy unit via an ethoxy chain. In the crystal, cations and anions are linked into chains by N—H⋯O and C—H⋯O hydrogen bonds.
In the title compound, C15H13ClO3S, the chlorothiophene and dimethoxyphenyl groups are linked by a prop-2-en-1-one group. The C=C double bond exhibits an E conformation. The molecule is non-planar, with a dihedral angle of 31.12 (5)° between the chlorothiophene and dimethoxyphenyl rings. The methoxy group at position 3 is coplanar with the benzene ring to which it is attached, with a C—O—C—C torsion angle of −3.8 (3)°. The methoxy group attached at position 2 of the benzene ring is in a (+)synclinal conformation, as indicated by the C—O—C—C torsion angle of −73.6 (2)°. In the crystal, two different C—H⋯O intermolecular interactions generate chains of molecules extending along the b axis.
The title compound crystallized with two independent molecules in the asymmetric unit. In the crystal, they are linked to one another, forming chains enclosing (10) and (12) ring motifs.
The title compound, C22H17NO4, crystallizes with two independent molecules (A and B) in the asymmetric unit. Each molecule exists as an E isomer with C—C=C—C torsion angles of −175.69 (17) and −178.41 (17)° in A and B, respectively. In molecule A, the planes of the terminal benzene rings are twisted by an angle of 26.67 (10)°, while the biphenyl unit is non-planar, the dihedral angle between the rings being 30.81 (10)°. The dihedral angle between the nitrophenyl ring and the inner phenyl ring is 6.50 (9)°. The corresponding values in molecule B are 60.61 (9), 31.07 (8) and 31.05 (9)°. In the crystal, molecules are arranged in a head-to-head manner, with the 3-nitrophenyl groups nearly parallel to one another. The A and B molecules are linked to one another via C—H⋯O hydrogen bonds, forming chains lying parallel to (-320) and enclosing R
2(10) and R
2(12) ring motifs. The methoxy group in both molecules is positionally disordered with a refined occupancy ratio of 0.979 (4):0.021 (4) for molecule A and 0.55 (4):0.45 (4) for molecule B.
crystal structure; chalcones; C—H⋯O hydrogen bonding; main-residue disorder
In the title compound, C18H18ClN5O3, the hydrazinecarboxamide N—N—C(O)—N unit is nearly planar [maximum deviation = 0.074 (2) Å] and is inclined at a dihedral angle of 57.43 (7)° with respect to the plane of the attached benzene ring. The chlorophenyl group makes dihedral angles of 19.71 (7) and 34.07 (6)° with the pyrazole and benzene rings, respectively. In the crystal, pairs of N—H⋯O hydrogen bonds link the molecules into inversion dimers that are further linked into chains along the a-axis direction by N—H⋯N hydrogen bonds. In addition, π–π stacking interactions are observed between benzene rings [centroid–centroid distance = 3.680 (1) Å].
The structure of the title compound, C15H10BrClO, comprises two substituted benzene rings bridged by a prop-2-en-1-one group and exists in an E configuration about the C=N double bond. The dihedral angle formed between the 4-bromophenyl and 2-chlorophenyl rings is 23.77 (18)°. In the crystal structure, the molecules are linked by weak C—H⋯O interactions, forming a supramolecular zigzag chain. Intramolecular C—H⋯Cl and C—H⋯O hydrogen bonds are also present.
In the title compound, C23H25ClF2N3O2
−, the triazole ring makes dihedral angles of 60.9 (4) and 25.0 (3)° with the 6-chlorophenyl and 2,4-difluorophenyl rings, respectively. The molecule adopts a Z configuration about the C=C double bond. In the crystal, the cations and anions are linked by N—H⋯O hydrogen bonds and weak C—H⋯O interactions.
The title compound, C15H10BrFO, is isostructural with (2E)-1-(4-chlorophenyl)-3-(4-fluorophenyl)prop-2-en-1-one [Qiu et al. (2006 ▶). Acta Cryst. E62, o3525–o3526], but the structures of other dihalogen analogues, without fluorine, are different, although they are also isostructural within the series. The molecule is approximately flat, the dihedral angle between the ring planes being 8.49 (13)°. In the crystal structure, intermolecular C—H⋯O, C—H⋯F and C—H⋯Br hydrogen bonds link molecules into V-shaped ribbons running parallel to  and stacked with an interplanar distance of approximately 3.53 Å (centroid–vcentroid distance = 3.857 Å)..
In the crystal structure of the title compound, C18H17FN4O2S·2H2O, the organic molecules are linked by intermolecular O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds with the water molecules, generating a three-dimensional network. The imidazole ring system forms a dihedral angle of 24.9 (2)° with the 4-fluorophenyl ring. The pyridine ring is oriented approximately perpendicular [72.24 (8)°] to the imidazole ring system.
In the title molecule, C16H15ClO4S, the chlorothiophene and trimethoxyphenyl rings make a dihedral angle of 31.12 (5)°. The C=C double bond exhibits an E conformation. In the crystal, C—H⋯O interactions generate bifurcated bonds, linking the molecules into chains along the b axis.