In the title compound, C24H27N3O5·H2O, the essentially planar benzimidazole ring system [maximum deviation = 0.020 (1) Å] forms dihedral angles of 54.10 (11) and 67.79 (6)°, respectively, with the mean plane of pyrrolidin-2-one ring and the benzene ring. The pyrrolidin-2-one ring adopts an envelope conformation with one of the methylene C atoms at the flap. An intramolecular C—H⋯π interaction is observed. In the crystal, O—H⋯O and O—H⋯N hydrogen bonds link the two components into a double-tape structure along the a axis. The crystal packing is further stabilized by weak π–π stacking [centroid–centroid distance = 3.6632 (9) Å] and 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.
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.
In the title compound, C28H27FN4O3·H2O, the benzimidazole ring system is essentially planar with a maximum deviation of 0.028 (1) Å. It makes dihedral angles of 47.59 (5) and 60.31 (5)°, respectively, with the pyridine and benzene rings, which make a dihedral angle of 22.58 (6)° with each other. The pyrrolidine ring shows an envelope conformation with one of the methylene C atoms as the flap. In the crystal, the components are connected into a tape along the b-axis direction through O—H⋯O and O—H⋯N hydrogen bonds and a π–π interaction between the pyridine and benzene rings [centroid–centroid distance of 3.685 (8) Å]. The tapes are further linked into layers parallel to the ab plane by C—H⋯O and C—H⋯F interactions.
In the title compound, C23H25N3O3, the benzimidazole ring system is essentially planar [maximum deviation = 0.0240 (18) Å]. The mean plane through this ring system forms a dihedral angle of 42.23 (7)° with the benzene ring. The pyrrolidine ring is in an envelope conformation with the flap atom disordered over two sites with occupancies of 0.813 (11) and 0.187 (11). In the crystal, weak C—H⋯O hydrogen bonds form R
2(10) ring motifs, which are connected by further C—H⋯O interactions, forming ribbons along the b axis. The crystal structure is further stabilized by weak π–π interactions involving the imidazole and benzene rings of the benzimidazole ring system [centroid–centroid distances = 3.6788 (11) and 3.6316 (10) Å] and weak C—H⋯π interactions.
In the title compound, C24H25N3O5, the benzimidazole and benzodioxole ring systems are each approximately planar [maximum deviations = 0.043 (1) and 0.036 (1) Å, respectively]. Their mean planes form a dihedral angle of 42.85 (4)°. The pyrrolidine ring has an envelope conformation with one of the methylene C atoms forming the flap. In the crystal, weak C—H⋯O hydrogen bonds link the molecules into a three-dimensional network. The crystal packing is further stabillized by weak π–π interactions between the benzene rings within the benzimidazole ring system [centroid–centroid distance = 3.7955 (7) Å]. A weak C—H⋯π interaction involving the benzodioxole ring is also present.
In the title compound, C24H25N3O5, the ethoxy group is disordered over two orientations in a 0.853 (14):0.147 (14) ratio. The benzimadazole ring system (r.m.s. deviation = 0.016 Å) makes a dihedral angle of 35.47 (7)° with the attached benzene ring. The pyrrolidine ring adopts an envelope conformation with a methylene C atom as the flap. In the crystal, inversion dimers linked by pairs of O—H⋯N hydrogen bonds generate R
2(16) loops. C—H⋯O interactions link the dimers into a three-dimensional network.
The title compound, C16H13NO3, crystallizes with two independent molecules (A and B) in the asymmetric unit. The dihedral angle between the mean planes of the 4-methylphenyl and 3-nitrophenyl groups is 4.0 (3)° in molecule A and 16.2 (7)° in molecule B. Intermolecular C—H⋯O hydrogen bonding involving the O atoms of the 3-nitrophenyl group of both independent molecules link the molecules into layers approximately parallel to the (110) plane. The layers are held together by π–π stacking interactions between the 4-methylphenyl ring of molecule A and the 3-nitrophenyl ring of molecule B of the adjacent layer, with the distance between the centroids of interacting rings being 3.6987 (7) Å.
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.
In the title compound, C20H17N3O4, the dihedral angles between the heterocyclic ring and the toluene and nitrobenzene rings are 4.21 (15) and 11.43 (14)°, respectively. The whole molecule is close to planar (r.m.s. deviation for the 27 non-H atoms = 0.171 Å). Two S(6) rings are formed due to intramolecular C—H⋯O and O—H⋯O hydrogen bonds. In the crystal, inversion dimers linked by pairs of C—H⋯O bonds generate R
2(10) loops and further C—H⋯O bonds link the dimers along the b-axis direction. There exist π–π interactions between the heterocyclic rings at a centroid–centroid distance of 3.7126 (10) Å and between the centroids of the benzene rings at a distance of 3.8710 (16) Å.
In the title molecule, C21H14BrFN4O4, the mean planes of the two nitro groups form dihedral angles of 3.1 (2) and 7.1 (5)° with the benzene ring to which they are attached. The dinitro-substituted ring forms dihedral angles of 8.6 (2) and 71.9 (2)° with the bromo- and fluoro-substituted benzene rings, respectively. The dihedral angle between the bromo- and fluoro-substituted benzene rings is 80.6 (2)°. There is an intramolecular N—H⋯O hydrogen bond. In the crystal, pairs of weak C—H⋯O hydrogen bonds form inversion dimers. In addition, π–π stacking interactions between the bromo- and dinitro-substituted rings [centroid–centroid separation = 3.768 (2) Å] are observed.
In the title Schiff base compound, C21H22Cl2N4S, the triazole ring makes dihedral angles of 2.15 (11) and 87.48 (11)° with the 2,6-dichlorophenyl and methylpropylphenyl rings, respectively. Weak intramolecular C—H⋯S and C—H⋯Cl interactions generate S(6) and S(5) ring motifs, respectively. In the crystal structure, centrosymmetrically related molecules are linked into dimers by N—H⋯S hydrogen bonds. These dimers are arranged into sheets parallel to the ab plane and are stacked along the c axis. C—H⋯π interactions involving the methylpropylphenyl ring and π–π interactions involving the dichlorophenyl ring [centroid–centroid distance = 3.5865 (3) Å] are also observed.
In the title compound, C24H15Cl2N3O3, the C=C double bond is E configured. The 1-phenyl-1H-pyrazole moiety is roughly planar (r.m.s. deviation of all fitted non-H atoms = 0.0780 Å), but the mean planes of the two components are inclined at an angle of 9.95 (7)°. The mean plane defined by the non-H atoms of the 1H-pyrazole ring encloses angles of 9.95 (7), 24.54 (6) and 43.02 (6)° with the mean planes of the different benzene rings. In the crystal, C—H⋯O contacts are present and result in the formation of a double-layer two-dimensional network lying parallel to (110). The shortest intercentroid distance between two aromatic systems is 3.5455 (7) Å and is apparent between two pyrazole systems. Further π–π interactions are manifest between a pair of 4-nitrophenyl rings [centroid-to-centroid distance = 3.6443 (7) Å] and a pair of 2,4-dichlorophenyl rings [centroid-to-centroid distance = 3.7797 (7) Å].
In the title compound, C17H14BrNO5, the dihedral angle between the 3-bromo-substituted benzene ring and the 4,5-dimethoxy-2-nitro-phenyl ring is 15.2 (1)°. The dihedral angles between the mean plane of the propenone group and the mean planes of the 3-bromo-substituted benzene and 4,5-dimethoxy-2-nitrophenyl rings are 6.9 (6) and 20.5 (5)°, respectively. Weak intermolecular C—H⋯O interactions contribute to crystal stability and π–π interactions [centroid–centroid distances = 3.7072 (18) and 3.6326 (18) Å] are also observed.
In the title compound, C29H28N4O3, the pyrrolidine ring adopts a twist conformation whereas the oxindole and benzimidazole residues are approximately planar with maximum deviations of 0.159 (1) and 0.011 (1) Å, respectively. The oxindole residue is almost perpendicular to the benzimidazole residue, making a dihedral angle of 89.2 (1)°. The methyl-substituted benzene ring is oriented at angles of 47.7 (1) and 71.0 (1)°, respectively, with respect to the oxindole and benzimidazole residues. An intramolecular C—H⋯O hydrogen bond is observed. In the crystal, molecules associate via N—H⋯N hydrogen bonds, forming R
The title co-crystal, 0.95C20H20O3·0.05C20H19ClO3, arises as the chloride carried over during the synthesis shares a position with an aromatic H atom; the partial occupancies are 0.947 (2) and 0.053 (2) for H and Cl, respectively. The molecular structure is stabilized by intramolecular C—H⋯O contacts, forming pseudo five- and six-membered rings with S(5) and S(6) graph-set motifs, respectively. The crystal structure features π–π stacking interactions between the centroids of the central fused ring systems [centroid–centroid distance = 3.501 (2) Å].
In the title compound, C23H22N4O4, the essentially planar [maximum deviation = 0.022 (1) Å] benzimidazole ring system forms dihedral angles of 86.16 (7) and 37.38 (6)°, respectively, with the imidazole and benzene rings. The dioxolane ring adopts an envelope conformation with the methylene C atom at the flap. In the crystal, C—H⋯O and C—H⋯N interactions link the molecules into a ribbon along the a axis. The crystal packing is further stabilized by weak π–π stacking interactions [centroid–centroid distances = 3.5954 (8) and 3.7134 (8) Å] and C—H⋯π interactions.
In the title molecule, C26H16BrN3O3, the anthracene and benzene mean planes make dihedral angles of 63.79 (2) and 14.67 (2)°, respectively, with the plane of the imidazole ring. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link molecules to form centrosymmetric dimers. Weak π–π stacking interactions, with centroid–centroid distances of 3.779 (2) and 3.826 (2) Å, supply additional stabilization. The crystal packing also exhibits short intermolecular contacts between the nitro groups and Br atoms [Br⋯O = 3.114 (2) Å].
In the title compound, C18H10Cl2O4, the chromen-2-one ring system is almost planar [maximum deviation = 0.028 (1) Å] and is inclined at an angle of 16.35 (4)° with respect to the benzene ring. The C=C bond has an E configuration. The molecular conformation is stabilized by an almost symmetric intramolecular O⋯H⋯O hydrogen bond and a C—H⋯O interaction, both of which form S(6) ring motifs. In the crystal structure, molecules are linked into sheets lying parallel to (100) via intermolecular C—H⋯O hydrogen bonds. The crystal packing is further consolidated by π–π stacking interactions [centroid-to-centroid separation = 3.6615 (6) Å].
In the title compound, C20H20N2O3, the piperidine ring adopts a chair conformation and its mean plane forms dihedral angles of 19.63 (9) and 19.44 (9)°, respectively, with the benzene and the nitro-substituted benzene ring. The benzene and nitro-substituted benzene rings are almost coplanar and make a dihedral angle of 4.78 (8)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds into two-dimensional networks parallel to the ab plane. The crystal packing is further stabilized by π–π interactions [maximum centroid–centroid distance = 3.7807 (12) Å].
The asymmetric unit of the title compound, C16H13NO3, contains two independent molecules related approximately by a pseudo-twofold rotation axis. The dihedral angle between the nitrobenzene and methylphenyl rings is 42.18 (6)° in one molecule and 12.97 (6)° in the other. In both molecules, the nitro group is slightly twisted away from the attached benzene ring. In the crystal structure, the molecules are stacked along the b axis and are linked via C—H⋯O and C—H⋯π interactions.
In the title compound, C13H10N2O3, the central C–C(=O)–N–C amide unit makes dihedral angles of 21.68 (4) and 19.08 (4)°, respectively, with the phenyl and nitrobenzene rings. The two aromatic rings are inclined at 3.74 (3)° and the nitro group is skewed out of the attached benzene ring plane by 18.55 (8)°. An intramolecular N—H⋯O interaction to an O atom of the nitro substituent generates an S(6) ring motif. In the crystal, C—H⋯O contacts generate two centrosymmetric ring systems with R
2(14) and R
2(20) graph-set motifs, forming zigzag chains down the a axis. π–π interactions between adjacent phenyl and nitrobenzene rings [centroid–centroid distance = 3.6849 (6) Å] also form centrosymmetric dimers. These and an additional C—H⋯O hydrogen bond generate an extensive three-dimensional network structure.
In the title compound, C26H24N2O2, the benzimidazole ring system is almost planar [maximum displacement = 0.025 (1) Å] and makes dihedral angles of 80.48 (5) and 41.57 (5)° with the benzene rings, which are inclined to one another by 65.33 (6)°. In the crystal, molecules are linked via C—H⋯π and weak π–π interactions [centroid–centroid distance = 3.8070 (7) Å and interplanar distance = 3.6160 (5) Å].
The crystal structures of the 1:1 salts of nicotine with 3,5-dinitrosalicylic acid and with 5-sulfosalicylic acid both show polymeric hydrogen-bonded and π–π-bonded structures but these differ in that in the first example, cations and anions form separate cation chains or anion columns which are unassociated through formal hydrogen bonds while in the second, hydrogen-bonded cation–anion chains are found.
The structures of the 1:1 anhydrous salts of nicotine (NIC) with 3,5-dinitrosalicylic acid (DNSA) and 5-sulfosalicylic acid (5-SSA), namely (1R,2S)-1-methyl-2-(pyridin-3-yl)-1H-pyrrolidin-1-ium 2-carboxy-4,6-dinitrophenolate, C10H15N2
−, (I), and (1R,2S)-1-methyl-2-(pyridin-3-yl)-1H-pyrrolidin-1-ium 3-carboxy-4-hydroxybenzenesulfonate, C10H15N2
+·C7H5O6S−, (II), are reported. The asymmetric units of both (I) and (II) comprise two independent nicotinium cations (C and D) and either two DNSA or two 5-SSA anions (A and B), respectively. One of the DNSA anions shows a 25% rotational disorder in the benzene ring system. In the crystal of (I), inter-unit pyrrolidinium N—H⋯Npyridine hydrogen bonds generate zigzag NIC cation chains which extend along a, while the DNSA anions are not involved in any formal inter-species hydrogen bonding but instead form π–π-associated stacks which are parallel to the NIC cation chains along a [ring-centroid separation = 3.857 (2) Å]. Weak C—H⋯O interactions between chain substructures give an overall three-dimensional structure. In the crystal of (II), A and B anions form independent zigzag chains with C and D cations, respectively, through carboxylic acid O—H⋯Npyridine hydrogen bonds. These chains, which extend along b, are pseudocentrosymmetrically related and give π–π interactions between the benzene rings of anions A and B and the pyridine rings of the NIC cations C and D, respectively [ring centroid separations = 3.6422 (19) and 3.7117 (19) Å]. Also present are weak C—H⋯O hydrogen-bonding interactions between the chains, giving an overall three-dimensional structure.
crystal structure; nicotine; proton-transfer salts; 3,5-dinitrosalicylic acid; 5-sulfosalicylic acid; hydrogen-bonding; π–π interactions
The molecule of the title compound, C20H16N2O5S, is built up by one fused five-membered and two fused six-membered rings linked to ethoxycarbonyl and 3-nitrophenyl groups. The benzothienopyran ring system is nearly planar (r.m.s deviation = 0.0392 Å) and forms a dihedral angle of 86.90 (6)° with the aromatic ring of the nitrobenzene group. In the crystal, molecules are linked by N—H⋯O hydrogen bonds and by π–π interactions between the phenyl ring and the six-membered heterocyle [intercentroid distance = 3.5819 (8) Å], forming a three-dimensional network.