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1.  Ethyl 2-(1,3-benzodioxol-5-yl)-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benz­imidazole-5-carboxyl­ate 
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.
doi:10.1107/S1600536812001420
PMCID: PMC3275223  PMID: 22347079
2.  Ethyl 2-(4-nitro­phen­yl)-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate 
In the title compound, C23H24N4O5, the essentially planar benzimidazole ring system [maximum deviation = 0.008 (2) Å] forms a dihedral angle of 39.22 (7)° with the attached nitro­benzene ring. The pyrrolidin-2-one ring adopts an envelope conformation with a C atom as the flap. In the crystal, mol­ecules are connected by C—H⋯O inter­actions, forming sheets propagating in (011). The crystal packing also features weak π–π stacking inter­actions [centroid–centroid = 3.6746 (12) Å].
doi:10.1107/S1600536811052408
PMCID: PMC3254415  PMID: 22259559
3.  Ethyl 2-[4-(morpholin-4-yl)phen­yl]-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-1,3-benzimidazole-5-carboxyl­ate monohydrate 
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.
doi:10.1107/S1600536812039268
PMCID: PMC3470336  PMID: 23125749
4.  Ethyl 1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-2-phenyl-1H-benzimidazole-5-carboxyl­ate 
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 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.
doi:10.1107/S1600536811054833
PMCID: PMC3274946  PMID: 22346899
5.  4-[1-(4-Cyano­benz­yl)-1H-benzimidazol-2-yl]benzonitrile 
In the title compound, C22H14N4, a new substituted benzimidazole, three inter­molecular C—H⋯N inter­actions link neighbouring mol­ecules into different dimers with R 2 2(12), R 2 2(8) and R 2 2(24) ring motifs. A fourth C—H⋯N inter­action links neighbouring mol­ecules along the c axis. There is also a short inter­molecular contact between the azomethine (C=N) segment of the benzimidazole ring and one of the C atoms of a neighbouring benzene ring [N⋯C = 3.191 (5), C⋯C = 3.364 (6) Å], which links the mol­ecules along the a axis. The two cyano­benzene rings are almost perpendicular to each other, with an inter­planar angle of 87.70 (7)°. The dihedral angles between the mean planes of the benzimidazole ring and the two outer benzene rings are 36.27 (16) and 86.70 (16)°. In the crystal structure, mol­ecules are stacked down the a axis with centroid–centroid distances of 3.906 (2)–3.912 (2) Å and inter­planar distances of 3.5040 (17) and 3.6235 (17) Å.
doi:10.1107/S1600536809006989
PMCID: PMC2969064  PMID: 21582406
6.  Ethyl 2-[5-(4-fluoro­phen­yl)pyridin-3-yl]-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate 
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.
doi:10.1107/S1600536813014177
PMCID: PMC3772454  PMID: 24046597
7.  Ethyl 2-(4-hy­droxy-3-meth­oxy­phen­yl)-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate monohydrate 
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.
doi:10.1107/S1600536811052391
PMCID: PMC3254439  PMID: 22259586
8.  Ethyl 1-(2-hy­droxy­eth­yl)-2-p-tolyl-1H-benzimidazole-5-carboxyl­ate 
The asymmetric unit of the title compound, C19H20N2O3, contains two mol­ecules (A and B) with slightly different orientations of the ethyl groups with respect to the attached carboxyl­ate groups. Intra­molecular C—H⋯O hydrogen bonds generate S(8) ring motifs in both mol­ecules A and B. In each mol­ecule, the benzimidazole ring system is essentially planar, with maximum deviations of 0.023 (1) and 0.020 (1) Å, respectively, for mol­ecules A and B. The dihedral angle between the benzimidazole ring system and the phenyl ring is 37.34 (5)° for mol­ecule A and 42.42 (5)° for mol­ecule B. In the crystal, O—H⋯N and C—H⋯O hydrogen bonds link the mol­ecules into [100] columns with a cross-section of two-mol­ecule by two-mol­ecule wide, and further stabilization is provided by weak C—H⋯π and π–π inter­actions [centroid separations = 3.5207 (7) and 3.6314 (8) Å].
doi:10.1107/S1600536810020799
PMCID: PMC3006903  PMID: 21587829
9.  2-Methyl-6-(6-methyl-1H-benzimidazol-2-yl)phenol–2-methyl-6-(5-methyl-1H-benzimidazol-2-yl)phenol (3/1) 
The title compound, 0.75C15H14N2O·0.25C15H14N2O, is a co-crystal of 2-methyl-6-(6-methyl-1H-benzimidazol-2-yl)phenol as the major component and 2-methyl-6-(5-methyl-1H-benz­imidazol-2-yl)phenol as the minor component. The refined site-occupancy ratio is 0.746 (4)/0.254 (4). The conformations of both components are identical except for that of the methyl substituent on the benzene ring of the benzimidazole unit which is positionally disordered over two positions. The mol­ecule is essentially planar, the dihedral angle between the benzimidazole plane and the benzene ring being 3.49 (4)°. An intra­molecular O—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal packing, mol­ecules are linked through N—H⋯O hydrogen bonds into chains along [201]. These chains are stacked approximately along the a-axis direction. The crystal packing is further stabilized by weak N—H⋯O and O⋯H⋯N hydrogen bonds, together with weak inter­molecular C—H⋯π inter­actions. A π–π inter­action with a centroid–centroid distance of 3.6241 (6) Å is also observed between the substituted phenyl ring and that of the benzimidazole system.
doi:10.1107/S1600536809049770
PMCID: PMC2972110  PMID: 21578934
10.  Methyl 7,8-diacet­oxy-11-oxo-5-(2-oxo­pyrrolidin-1-yl)-7,9-epoxy­cyclo­penta­[4,5]pyrido[1,2-a]quinoline-10-carboxyl­ate sesquihydrate 
The title compound, C26H28N2O9·1.5H2O, the product of an acid-catalysed Wagner–Meerwein skeletal rearrangement, crystallizes as a sesquihydrate with the O atom of one of the two independent water mol­ecules occupying a special position on a twofold axis. The organic mol­ecule comprises a fused penta­cyclic system containing two five-membered rings (cyclo­pentane and tetra­hydro­furan) and three six-membered rings (piperidinone, tetra­hydro­pyridine and benzene). The five-membered rings have the usual envelope conformations, and the central six-membered piperidinone and tetra­hydro­pyridine rings adopt boat and sofa conformations, respectively. In the crystal, there are three independent O—H⋯O hydrogen bonds, which link the organic mol­ecules and water mol­ecules into complex two-tier layers parallel to (001). The layers are further linked into a three-dimensional framework by attractive inter­molecular carbon­yl–carbonyl inter­actions.
doi:10.1107/S160053680905363X
PMCID: PMC2980137  PMID: 21580091
11.  2-Meth­oxy-6-(6-methyl-1H-benzimid­azol-2-yl)phenol 
In the title mol­ecule, C15H14N2O2, the substituted benzene ring forms a dihedral angle of 4.15 (1)° with the benzimidazole ring system. An intra­molecular O—H⋯N hydrogen bond generates an S(6) ring motif. In the solid state, mol­ecules are linked into chains along the [001] via inter­molecular bifurcated N—H⋯(O,O) hydrogen bonds, which generate R 1 2(5) ring motifs. The crystal packing is also consolidated by C—H⋯π inter­actions, and π–π stacking inter­actions between the imidazole and substituted benzene rings [centroid–centroid distance = 3.5746 (13) Å]. The methyl group attached to the benzimidazole ring system is disordered over two positions with occupancies of 0.587 (6) and 0.413 (6), suggesting 180° rotational disorder for the benzimidazole group.
doi:10.1107/S1600536809022478
PMCID: PMC2969490  PMID: 21582885
12.  2-[1-(2-Hydroxy-3-methoxybenzyl)-1H-benzimidazol-2-yl]-6-methoxyphenol monohydrate 
The asymmetric unit of the title compound, C22H20N2O4·H2O, comprises a substituted benzimidazole molecule and a water mol­ecule of crystallization. The dihedral angles between the benzimidazole ring system and the two outer benzene rings are 16.54 (4) and 86.13 (4)°. The dihedral angle between the two hydr­oxy-substituted benzene rings is 82.20 (5)°. In the crystal structure, inter­molecular O—H⋯O hydrogen bonds, involving the hydr­oxy groups and water mol­ecules, form R 4 4(8) ring motifs, and link symmetry-related mol­ecules into extended chains along the c axis. The crystal structure is further stabilized by weak inter­molecular C—H⋯O hydrogen bonds, weak C—H⋯π and π–π stacking [centroid–centroid = 3.6495 (6)–3.7130 (6) Å] inter­actions. Intra­molecular O—H⋯O and O—H⋯N inter­actions are also present.
doi:10.1107/S1600536809010769
PMCID: PMC2968983  PMID: 21582616
13.  1,4-Bis(1H-benzimidazol-2-yl)benzene methanol monosolvate 
The asymmetric unit of the title compound, C20H14N4·CH4O, contains two independent half-mol­ecules, each located on an inversion centre, and a methanol solvent mol­ecule. The benzimidazolyl groups form different dihedral angles [24.0 (1) and 11.6 (1)°] with the plane of the central benzene ring in the two mol­ecules. In the crystal, a two-dimensional network is formed through N—H⋯ N, N—H⋯O and O—H⋯N hydrogen-bonding inter­actions between the benzimidazole units and methanol solvent mol­ecules. π–π stacking inter­actions also occur between the benzimidazole rings of adjacent mol­ecules, with centroid–centroid distances of 3.720 (14) Å and inter­planar distances of 3.53 (1) Å .
doi:10.1107/S1600536810049238
PMCID: PMC3050263  PMID: 21522799
14.  Crystal structure of methyl 6-meth­oxy-11-(4-meth­oxy­phen­yl)-16-methyl-14-phenyl-8,12-dioxa-14,15-di­aza­tetra­cyclo­[8.7.0.02,7.013,17]hepta­deca-2(7),3,5,13(17),15-penta­ene-10-carboxyl­ate 
In the title compound, the pyran and pyrone rings adopt slightly distorted half-chair and envelope conformations, respectively. In the crystal, C—H⋯O and π–π inter­actions connect the mol­ecules, forming double layers that stack along the c-axis direction.
In the title compound, C30H28N2O6, the pyran ring adopts a slightly distorted half-chair conformation and the pyrone ring adopts an envelope conformation, with the C atom bearing the carboxyl­ate group as the flap. The pyrazole ring [maximum deviation = 0.002 (2) Å] forms a dihedral angle of 13.2 (1)° with the attached benzene ring. The near-planar atoms of the pyran ring and the pyrazole ring are close to coplanar, the dihedral angles between their mean planes being 6.4 (1)°. The dihedral angle between the pyrone ring and the benzene ring of the chromene unit is 10.7 (1)°. The mol­ecular conformation is stabilized by an intra­molecular C—H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, C—H⋯O inter­actions generate supra­molecular chains propagating in [100] and these are connected into double layers that stack along the c-axis direction by weak π–π inter­actions between pyrazole rings [centroid–centroid distance = 3.801 (1) Å].
doi:10.1107/S1600536814017929
PMCID: PMC4186142  PMID: 25309159
crystal structure; conformation; crystal packing; chromene
15.  2-(1H-Benzoimidazol-2-yl)-6-ethoxy­phenol 
The title Schiff base compound, C15H14N2O2, consists of two crystallographically independent mol­ecules, A and B. Mol­ecule A is almost planar, whereas mol­ecule B is slightly twisted, the dihedral angles between the benzimidazole group and the benzene rings being 2.65 (12) and 13.17 (15)°, respectively. The methyl group of mol­ecule B is disordered over two positions, with a refined site-occupancy ratio of 0.581 (7):0.419 (7). In each mol­ecule, intra­molecular O—H⋯N hydrogen bonds generate S(6) ring motifs. In the crystal structure, both types of mol­ecules are linked via inter­molecular bifurcated N—H⋯O hydrogen bonds into one-dimensional extended chains along [010] and form R 1 2(5) ring motifs. The crystal structure is further stabilized by inter­molecular C—H⋯π and π–π inter­actions [centroid–centroid distances = 3.4758 (16)–3.596 (2) Å].
doi:10.1107/S1600536809008071
PMCID: PMC2969036  PMID: 21582478
16.  1-{2-(4-Chloro­benz­yloxy)-2-[4-(mor­pho­lin-4-yl)phen­yl]eth­yl}-1H-benzimidazole propan-2-ol monosolvate 
In the title compound, C26H26ClN3O2·C3H7OH, the benzimid­azole ring system is essentially planar [maximum deviation = −0.018 (2) Å] and its mean plane is oriented with respect to the two benzene rings at dihedral angles of 4.51 (6) and 56.16 (6)°, and the dihedral angle between the two benzene rings is 59.11 (7)°. The morpholine ring displays a chair conformation. The propan-2-ol solvent mol­ecule links with the benzimidazole ring via an O—H⋯N hydrogen bond. In the crystal, weak inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into inversion dimers with an R 2 2(28) motif. π–π stacking occurs between the parallel chloro­benzene rings [centroid–centroid distance = 3.792 (1) Å]. Weak C—H⋯π inter­actions and short Cl⋯Cl [3.2037 (10) Å] contacts are also observed.
doi:10.1107/S1600536813022599
PMCID: PMC3884486  PMID: 24427066
17.  1-[4-(Difluoro­meth­oxy)phen­yl]-N-(3,4-dimeth­oxy­phen­yl)-1H-1,2,4-triazole-3-carboxamide 
Two crystallographically independent mol­ecules, A and B, with similar conformations are present in the asymmetric unit of the title compound, C18H16F2N4O4. In mol­ecule A, the plane of the 1,2,4-triazole ring is tilted relative of the 4-difluoro­meth­oxy-substituted and the 3,4-dimeth­oxy-substituted benzene rings by 6.5 (2) and 16.4 (1)°, respectively. The –CHF2 group is twisted away from the plane of the benzene ring, with a dihedral angle between the O—C bond of the OCHF2 group and the plane of the adjacent phenyl ring of 38.6 (3)°. The corresponding parameters for mol­ecule B are 7.7 (1), 9.5 (2) and 25.2 (2)°. In both mol­ecules, the conformations are stabilized by intra­molecular N—H⋯N and C—H⋯O hydrogen bonds. There are also C—H⋯π contacts between the methyl groups and the benzene rings, and π–π stacking inter­actions between the benzene rings of adjacent parallel A mol­ecules [centroid–centroid distance = 3.8942 (17) Å]. π–π inter­actions are also observed between the triazole ring and one of the benzene rings of parallel B mol­ecules [centroid–centroid distance = 3.7055 (16) Å].
doi:10.1107/S1600536810029661
PMCID: PMC3007844  PMID: 21588626
18.  Diaqua­bis[4-(dimethyl­amino)benzoato](isonicotinamide)zinc(II) 
The mol­ecule of the title ZnII complex, [Zn(C9H10NO2)2(C6H6N2O)(H2O)2], contains two 4-(dimethyl­amino)benzoate (DMAB) ligands, one isonicotinamide (INA) ligand and two water mol­ecules; one of the DMAB ions acts as a bidentate ligand while the other and INA are monodentate ligands. The four O atoms in the equatorial plane around the Zn atom form a distorted square-planar arrangement, while the distorted octa­hedral coordination is completed by the N atom of the INA ligand and the O atom of the water mol­ecule in the axial positions. Intra­molecular C—H⋯O hydrogen bonding results in the formation of a six-membered ring adopting an envelope conformation. The dihedral angle between the carboxyl groups and the adjacent benzene rings are 4.87 (16) and 2.2 (2)°, while the two benzene rings are oriented at a dihedral angle of 65.13 (8)°. The dihedral angle between the benzene and pyridine rings are 11.47 (7) and 74.83 (8)°, respectively. In the crystal structure, inter­molecular O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds link the mol­ecules into a supra­molecular structure. π–π contacts between the pyridine and benzene rings and between the benzene rings [centroid–centroid distances = 3.695 (1) and 3.841 (1) Å, respectively] further stabilize the structure. Weak inter­molecular C—H⋯π inter­actions are also present.
doi:10.1107/S1600536809017620
PMCID: PMC2969605  PMID: 21583016
19.  6-Chloro-N-(2-meth­oxy­phen­yl)pyridazin-3-amine 
The asymmetric unit of the title compound, C11H10ClN3O, contains two geometrically different mol­ecules, A and B, in both of which the pyridazine rings are essentially planar with r.m.s. deviations of 0.0137 and 0.0056Å, respectively. In mol­ecule A, the dihedral angle between the pyridazine and benzene rings is 6.5 (2)°, whereas in mol­ecule B it is 27.93 (7)°. In mol­ecule B, an intramolecular N—H⋯O hydrogen bond forms an S(5) ring motif. In both molecules, S(6) ring motifs are present due to non-classical C—H⋯N hydrogen bonds. The π–π inter­actions between the pyridazine rings of A mol­ecules [3.4740 (13) Å] and B mol­ecules [3.4786 (17) Å] have very similar centroid–centroid separations. π–π Inter­actions also occur between the benzene rings of B mol­ecules with a centroid–centroid separation of 3.676 (2) Å and a slippage of 1.02 Å. In the crystal, the mol­ecules are linked into chains extending along [010] by C—H⋯N and C—H⋯Cl interactions.
doi:10.1107/S1600536812001535
PMCID: PMC3275194  PMID: 22347050
20.  N-(2,4-Dimethyl­phen­yl)-2,2-diphenyl­acetamide 
The asymmetric unit of the title compound, C22H21NO, consists of two crystallographically independent mol­ecules (A and B). Each mol­ecule contains two benzene rings and one dimethyl­benzene ring. The dihedral angle between the two benzene rings is 87.75 (16)° in mol­ecule A and 89.25 (16)° in mol­ecule B. In mol­ecule A, the dimethyl­benzene ring forms dihedral angles of 89.65 (8) and 42.98 (11)° with the two benzene rings, whereas the corresponding angles are equal to 63.15 (7) and 58.67 (10)° in mol­ecule B. An intra­molecular C—H⋯O hydrogen bond generates an S(6) ring motif in each mol­ecule. In the crystal, mol­ecules are linked by bifurcated (N,C)—H⋯O hydrogen bonds, generating R 2 1(6) ring motifs and forming infinite chains along the a axis. The crystal is further stabilized by C—H⋯π and π–π inter­actions with centroid–centroid distances of 3.8543 (18) and 3.930 (2) Å.
doi:10.1107/S1600536812014079
PMCID: PMC3344457  PMID: 22590219
21.  Crystal structure of 1,3-bis­(4-methyl­benz­yl)-1H-1,3-benzimidazol-3-ium bromide monohydrate 
In the title hydrated symetrically substituted 1,3-bis­(4-methyl­benz­yl)benzimidazolium salt, C23H23N2 +·Br−·H2O, the dihedral angles between the benzimidazole ring system (r.m.s. deviation = 0.003 Å) and the pendant benzene rings are 73.18 (16) and 77.52 (16)°. Both benzene rings lie to the same side of the benzimidazole ring system, giving the cation an overall U-shape. In the crystal, the cation is linked to the water mol­ecule by a short C—H⋯O hydrogen bond and the water mol­ecule forms O—H⋯Br hydrogen bonds. Together, these inter­actions lead to [010] chains. The packing is consolidated by C—H⋯Br hydrogen bonds and aromatic π–π stacking inter­actions [centroid–centroid distances = 3.5401 (17) and 3.8815 (18) Å], generating a three-dimensional network.
doi:10.1107/S2056989014025857
PMCID: PMC4331869
crystal structure; 1,3-bis­(4-methyl­benz­yl)-1H-3,1-benzimidazol-3-ium bromide monohydrate; benzimidazolium salts; N-heterocyclic carbenes; hydrogen bonds; aromatic π–π stacking inter­actions
22.  1-Benzyl-3-[(trimethyl­sil­yl)meth­yl]benzimidazolium chloride monohydrate 
The title compound, C18H23N2Si+·Cl−·H2O, was synthesized from 1-[(trimethyl­sil­yl)meth­yl]benzimidazole and benzyl chloride in dimethyl­formamide. The benzimidazole ring system is approximately planar, with a maximum deviation of 0.022 (2) Å, and makes an angle of 74.80 (12)° with the phenyl ring. The crystal packing is stabilized by O—H⋯Cl, C—H⋯Cl, C—H⋯O and C—H⋯π inter­actions between symmetry-related mol­ecules together with π–π stacking inter­actions between the imidazolium and benzene rings [centroid–centroid distance = 3.5690 (15) Å] and between the benzene rings [centroid–centroid distance = 3.7223 (14) Å].
doi:10.1107/S1600536810024128
PMCID: PMC3007035  PMID: 21587984
23.  2-(4-Hy­droxy­phen­yl)-1H-benzimidazol-3-ium chloride monohydrate 
The title mol­ecular salt, C13H11N2O+·Cl−·H2O, crystallizes as a monohydrate. In the cation, the phenol and benzimidazole rings are almost coplanar, making a dihedral angle of 3.18 (4)°. The chloride anion and benzimidazole cation are linked by two N+—H⋯Cl− hydrogen bonds, forming chains propagating along [010]. These chains are linked through O—H⋯Cl hydrogen bonds involving the water mol­ecule and the chloride anion, which form a diamond core, giving rise to the formation of two-dimensional networks lying parallel to (10-2). Two π–π inter­actions involving the imidazolium ring with the benzene and phenol rings [centroid–centroid distances = 3.859 (3) and 3.602 (3) Å, respectively], contribute to this second dimension. A strong O—H⋯O hydrogen bond involving the water mol­ecule and the phenol substituent on the benzimidazole unit links the networks, forming a three-dimensional structure.
doi:10.1107/S1600536813023441
PMCID: PMC3884505  PMID: 24427105
24.  4-Chloro-2-(6-nitro-1H-benzimidazol-2-yl)phenol N,N-dimethyl­form­amide solvate 
In the title compound, C13H8ClN3O3·C3H7NO, the benzimidazole and benzene rings make a dihedral angle of 0.63 (11)°. An intra­molecular O—H⋯N hydrogen bond generates an S(6) ring motif. The solvent mol­ecule is hydrogen-bonded to the benzimidazole mol­ecule by inter­molecular N—H⋯O and C—H⋯O hydrogen bonds, generating an R 1 2(7) ring motif. In the crystal, the mol­ecules are arranged into parallel layers perpendicular to the c axis and stabilized by weak π–π inter­actions [centroid–centroid distances in the range 3.4036 (18)–3.5878 (16) Å].
doi:10.1107/S1600536810041243
PMCID: PMC3009370  PMID: 21589045
25.  1,3-Bis(3-phenyl­prop­yl)benzimidazolium bromide monohydrate 
In the title compound, C25H27N2 +·Br−·H2O, the benzimidazole unit is essentially planar, with a maximum deviation of 0.020 (6) Å. The benzimidazole unit makes dihedral angles of 83.6 (3) and 81.0 (3)° with the two terminal phenyl rings. The dihedral angle between the phenyl rings is 58.5 (4)°. In the crystal structure, there are C—H⋯O hydrogen bonds, a C—H⋯π inter­action between a phenyl H atom and the phenyl ring of a neighbouring mol­ecule, and a π–π inter­action [3.512 (3) Å] between the centroids of the five-membered ring and the benzene ring of the benzimidazole unit of an adjacent mol­ecule.
doi:10.1107/S1600536808030432
PMCID: PMC2959260  PMID: 21201214

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