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Ethyl 1-(2-hy-droxy-eth-yl)-2-propyl-1H-benzimidazole-5-carboxyl-ate.

ABSTRACT: In the title compound, C(15)H(20)N(2)O(3), the benzimidazole ring is essentially planar, with a maximum deviation from the mean plane of 0.012?(1)?Å. The crystal structure is stabilized by inter-molecular O-H?N hydrogen bonds, forming centrosymmetric dimers, which are connected in the [100] direction through weak C-H?O contacts.

SUBMITTER: Hamzah N

PROVIDER: S-EPMC3201285 | biostudies-literature | 2011 Oct

REPOSITORIES: biostudies-literature

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Ethyl 1-(2-hy-droxy-eth-yl)-2-propyl-1H-benzimidazole-5-carboxyl-ate.

Hamzah Nurasyikin N Ngah Nurziana N Abd Hamid Shafida S Abdul Rahim Aisyah Saad AS

Acta crystallographica. Section E, Structure reports online 20110930 Pt 10

In the title compound, C(15)H(20)N(2)O(3), the benzimidazole ring is essentially planar, with a maximum deviation from the mean plane of 0.012 (1) Å. The crystal structure is stabilized by inter-molecular O-H⋯N hydrogen bonds, forming centrosymmetric dimers, which are connected in the [100] direction through weak C-H⋯O contacts. ...[more]

PMID: 22058794

Similar Datasets

Ethyl 1-(2-hy-droxy-eth-yl)-2-phenyl-1H-benzimidazole-5-carboxyl-ate.

Project description:There are two mol-ecules in the asymmetric unit of the title compound, C(18)H(18)N(2)O(3). In each one, the benzimidazole ring system is essentially planar, with maximum deviations of 0.027?(1) and 0.032?(1)Å, and makes dihedral angles of 38.64?(6) and 41.48?(6)°, respectively, with the attached benzene rings. An intra-molecular C-H?O hydrogen bond is observed in each mol-ecule. The two independent mol-ecules are connected into a dimer by two inter-molecular O-H?N hydrogen bonds. In the crystal, mol-ecules form a two-dimensional layers parallel to (012) via weak inter-molecular C-H?O hydrogen bonds. In addition, weak ?-? stacking inter-actions are observed with centroid-centroid distances of 3.5244?(12) and 3.6189?(12)?Å.

| S-EPMC3006730 | biostudies-literature

Ethyl 1-(2-hy-droxy-eth-yl)-2-(4-meth-oxy-phen-yl)-1H-benzimidazole-5-carboxyl-ate monohydrate.

Project description:In the title mol-ecule, C(19)H(20)N(2)O(4)·H(2)O, the benzimidazole ring system is essentially planar [maximum deviation = 0.013?(11)?Å] and is inclined to the 4-meth-oxy-phenyl ring by 30.98?(5)°. In the crystal, O-H?O and O-H?N hydrogen bonds involving the water mol-ecule link neighbouring mol-ecules, forming a two-dimensional network lying parallel to the bc plane. There are also C-H?? and ?-? inter-actions present. The latter involve inversion-related benzimidazole rings with centroid-centroid distances of 3.5552?(8) and 3.7466?(8)?Å.

| S-EPMC3275179 | biostudies-literature

Ethyl 1-(2-hy-droxy-eth-yl)-2-p-tolyl-1H-benzimidazole-5-carboxyl-ate.

Project description:The asymmetric unit of the title compound, C(19)H(20)N(2)O(3), contains two mol-ecules (A and B) with slightly different orientations of the ethyl groups with respect to the attached carboxyl-ate groups. Intra-molecular C-H?O hydrogen bonds generate S(8) ring motifs in both mol-ecules A and B. In each mol-ecule, the benzimidazole ring system is essentially planar, with maximum deviations of 0.023?(1) and 0.020?(1)?Å, respectively, for mol-ecules A and B. The dihedral angle between the benzimidazole ring system and the phenyl ring is 37.34?(5)° for mol-ecule A and 42.42?(5)° for mol-ecule B. In the crystal, O-H?N and C-H?O hydrogen bonds link the mol-ecules into [100] columns with a cross-section of two-mol-ecule by two-mol-ecule wide, and further stabilization is provided by weak C-H?? and ?-? inter-actions [centroid separations = 3.5207?(7) and 3.6314?(8)?Å].

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Ethyl 1-(2-hy-droxy-eth-yl)-2-[2-(methyl-sulfan-yl)eth-yl]-1H-benzimidazole-5-carboxyl-ate.

Project description:In the crystal structure of the title compound, C(15)H(20)N(2)O(3)S, the hy-droxy group is involved in the formation of O-H?N hydrogen bonds, which link two mol-ecules into a centrosymmetric dimer. Weak C-H?O hydrogen bonds further link these dimers into chains propagating along the a axis. The crystal packing exhibits ?-? inter-actions between the five- and six-membered rings of neighbouring mol-ecules [centroid-centroid distance = 3.819?(2)?Å] and short inter-molecular S?S contacts of 3.495?(1)?Å.

| S-EPMC3254533 | biostudies-other

Ethyl 2-(4-hy-droxy-3-meth-oxy-phen-yl)-1-[3-(2-oxopyrrolidin-1-yl)prop-yl]-1H-benzimidazole-5-carboxyl-ate monohydrate.

Project description:In the title compound, C(24)H(27)N(3)O(5)·H(2)O, 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 intra-molecular C-H?? inter-action 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 ?-? stacking [centroid-centroid distance = 3.6632?(9)?Å] and C-H?O inter-actions.

| S-EPMC3254439 | biostudies-literature

Ethyl 1-[2-(morpholin-4-yl)eth-yl]-2-[4-(morpholin-4-yl)phen-yl]-1H-1,3-benzimidazole-5-carboxyl-ate.

Project description:The asymmetric unit of the title compound, C(26)H(32)N(4)O(4), consists of two independent mol-ecules. In both mol-ecules, the eth-oxy groups are each disordered over two sets of sites with occupancies of 0.695?(4):0.305?(4) and 0.877?(2):0.123?(2). The dihedral angles between the benzimidazole ring system and the adjacent benzene ring in the two mol-ecules are 41.41?(5) and 31.46?(5)°. In the crystal, mol-ecules are linked by C-H?O and C-H?N inter-actions.

| S-EPMC3152030 | biostudies-literature

Ethyl (Z)-4'-(4-eth-oxy-1-hy-droxy-3,4-dioxobut-1-en-1-yl)-[1,1'-biphen-yl]-3-carboxyl-ate.

Project description:The 1,3-diketone group of the title compound, C21H20O6, exists in a keto-enol form stabilized by a strong intra-molecular O-H?O hydrogen bond. As a result, a planar (mean deviation = 0.0099?Å) six-membered hydrogen-bonded ring is formed. The C-O and C-C bond lengths suggest significant electron delocalization in the ring. The dihedral angle between the six-membered hydrogen-bonded ring and its adjacent benzene ring is 8.78?(5)° and that between the benzene rings is 19.70?(5)°. In the crystal, mol-ecules are packed in a layered structure parallel to the b axis through C-H?O and ?-? inter-actions [centroid-centroid distance between stacked benzene rings = 3.868?(2)?Å].

| S-EPMC3793735 | biostudies-literature

Ethyl 2-(4-bromo-phen-yl)-1-phenyl-1H-benzimidazole-5-carboxyl-ate.

Project description:In the title compound, C(22)H(17)BrN(2)O(2), the benzimidazole ring system is essentially planar, with a maximum deviation of 0.017?(1)?Å, and forms dihedral angles of 27.79?(6) and 64.43?(6)° with the phenyl and bromo-substituted benzene rings, respectively. In the crystal, mol-ecules are linked into one-dimensional chains along the a axis by weak C-H?O hydrogen bonds. Weak inter-molecular C-H?? inter-actions are also present.

| S-EPMC3379279 | biostudies-literature

Ethyl 2-(4-chloro-phen-yl)-1-phenyl-1H-benzimidazole-5-carboxyl-ate.

Project description:In the title compound, C(22)H(17)ClN(2)O(2), the essentially planar benzimidazole ring system [maximum deviation = 0.012?(2)?Å] forms dihedral angles of 28.69?(6) and 63.65?(7)°, respectively, with the phenyl and chloro-substituted benzene rings. The dihedral angle between the phenyl and benzene rings is 64.23?(8)°. In the crystal, mol-ecules are linked into a zigzag chain along the a axis by inter-molecular C-H?O hydrogen bonds. C-H?? inter-actions are also present.

| S-EPMC3379429 | biostudies-literature

2-sec-Butyl-1-(2-hy-droxy-eth-yl)-1H-benzimidazole-5-carboxylic acid.

Project description:In the title compound, C(14)H(18)N(2)O(3), the carb-oxy-lic group is tilted by 12.00?(4)° with respect to the mean plane throught the benzimidazole ring system. The alcohol and carboxyl hydroxy groups are involved in intermolecular O-H?O and O-H?N hydrogen bonds, forming a two-dimensional network extending parallel the ab plane. The network is further stabilized by weak C-H?O inter-actions. The sec-butyl group is disordered over two sets of sites with refined occupancies of 0.484?(4) and 0.516?(4).

| S-EPMC3393269 | biostudies-literature

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