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Second monoclinic polymorph of 4-[(1H-benzimidazol-1-yl)meth-yl]benzoic acid.

ABSTRACT: Recently, we reported the first monoclinic [Kuai & Cheng (2011). Acta Cryst., E67, o2787] and the ortho-rhom-bic polymorph [Kuai & Cheng (2011). Acta Cryst., E67, o3014] of the title compound, C(15)H(12)N(2)O(2). Another monoclinic polymorph was obtained accidentally by the hydro-thermal reaction of the title compound with manganese chloride in the presence of potassium hydroxide at 413 K. The asymmetric unit consists of four independent mol-ecules. In the crystal, O-H⋯N hydrogen bonds link the independent mol-ecules into four separate chains parallel to the b axis.

SUBMITTER: Kuai HW

PROVIDER: S-EPMC3238873 | biostudies-literature | 2011 Dec

REPOSITORIES: biostudies-literature

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Second monoclinic polymorph of 4-[(1H-benzimidazol-1-yl)meth-yl]benzoic acid.

Kuai Hai-Wei HW Cheng Xiao-Chun XC

Acta crystallographica. Section E, Structure reports online 20111105 Pt 12

Recently, we reported the first monoclinic [Kuai & Cheng (2011). Acta Cryst., E67, o2787] and the ortho-rhom-bic polymorph [Kuai & Cheng (2011). Acta Cryst., E67, o3014] of the title compound, C(15)H(12)N(2)O(2). Another monoclinic polymorph was obtained accidentally by the hydro-thermal reaction of the title compound with manganese chloride in the presence of potassium hydroxide at 413 K. The asymmetric unit consists of four independent mol-ecules. In the crystal, O-H⋯N hydrogen bonds link the ...[more]

PMID: 22199726

Similar Datasets

Monoclinic polymorph of 4-[(1H-benz-imidazol-1-yl)meth-yl]benzoic acid.

Project description:Three polymorphs of the title compound, C(15)H(12)N(2)O(2), were obtained accidentally as single crystals in the hydro-thermal reaction of the title compound with manganese bromide in the presence of N,N'-dimethyl-formamide at 373 K. Here we report the structure of the first polymorph. The benzimidazole ring is almost planar, the maximum deviation from the mean plane being 0.016 (1) Å. The benzimidazole and benzene rings are approximately perpendicular, making a dihedral angle 85.56 (7)°, which is a reflection of the axial rotation of the flexible benzimidazolyl arm. In the crystal, adjacent mol-ecules are connected through O-H⋯N hydrogen bonds into a chain along [100], and neighboring chains are further linked by via weak C-H⋯O hydrogen-bonding inter-actions, forming a two-dimensional network.

| S-EPMC3201311 | biostudies-literature

Ortho-rhom-bic polymorph of 4-[(1H-benzimidazol-1-yl)meth-yl]benzoic acid.

Project description:We reported recently the first polymorph of the title compound [Kuai & Cheng (2011a ▶). Acta Cryst., E67, o2787]. A second polymorph of the title compound, C(15)H(12)N(2)O(2), was unexpectedly obtained by the hydro-thermal reaction of the title compound with manganese chloride in the presence of potassium hydroxide at 413 K. The benzimidazole ring system is almost planar, with a maximum deviation from the mean plane of 0.015 (2) Å. The benzimidazole and benzene rings are inclined at a dihedral angle of 79.00 (1)°. In the crystal, adjacent mol-ecules are connected through O-H⋯N hydrogen bonds into a one-dimensional chain along the [001] direction.

| S-EPMC3247413 | biostudies-literature

A monoclinic polymorph of 5-[(1H-benzimidazol-1-yl)meth-yl]benzene-1,3-dicarb-oxy-lic acid.

Project description:Crystals of the title compound, C(16)H(12)N(2)O(4), were obtained accidentally by the hydro-thermal reaction of 5-[(1H-benzo[d]imidazol-1-yl)meth-yl]isophthalic acid with manganese chloride tetra-hydrate in the presence of KOH as alkaline reagent for the deprotonation. A triclinic polymorph of this structure has been reported previously from a similar reaction [Cheng (2011 ▶). Acta Cryst. E67, o3299]. The benzimidazole ring system is almost planar, with a maximum deviation from the mean plane of 0.020 (4) Å. The benzimidazole unit and benzene ring are inclined at a dihedral angle of 68.17 (4)°, reflecting the axial rotation of the flexible benzimidazolyl arm. In the crystal, pairs of O-H⋯O hydrogen bonds link adjacent mol-ecules into inversion dimers. O-H⋯N contacts connect these dimers into zigzag chains along [010].

| S-EPMC3515175 | biostudies-literature

Crystal structure of a second monoclinic polymorph of 3-meth-oxy-benzoic acid with Z' = 1.

Project description:A new polymorphic form of the title compound, C8H8O3, is described in the centrosymmetric monoclinic space group P21/c with Z' = 1 as compared to the first polymorph, which crystallizes with two conformers (Z' = 2) in the asymmetric unit in the same space group. In the crystal of the second polymorph, inversion dimers linked by O-H⋯O hydrogen bonds occur and these are linked into zigzag chains, propagating along the b-axis direction by C-H⋯O links. The crystal structure also features a weak π-π inter-action, with a centroid-to-centroid distance of 3.8018 (6) Å. The second polymorph of the title compound is less stable than the reported first polymorph, as indicated by its smaller calculated lattice energy.

| S-EPMC6323879 | biostudies-literature

Bis[2-(hy-droxy-imino-meth-yl)phenolato]nickel(II): a second monoclinic polymorph.

Project description:The title compound, [Ni(C(7)H(6)NO(2))(2)], (I), is a second monoclinic polymorph of the compound, (II), reported by Srivastava et al. [Acta Cryst. (1967), 22, 922] and Mereiter [Private communication (2002) CCDC refcode NISALO01]. The bond lengths and angles are similar in both structures. The mol-ecule in both structures lies on a crystallographic inversion center and both have an inter-nal hydrogen bond. The title compound crystallizes in the space group P2(1)/c (Z = 2), whereas compound (II) is in the space group P2(1)/n (Z = 2) with a similar cell volume but different cell parameters. In both polymorphs, mol-ecules are arranged in the layers but in contrast to the previously published compound (II) where the dihedral angle between the layers is 86.3°, in the title polymorph the same dihedral angle is 29.4°. The structure of (I) is stabilized by strong intra-molecular O-H⋯O hydrogen bonding between the O-H group and the phenolate O atom.

| S-EPMC3051639 | biostudies-literature

A new polymorph of 2,6-bis-(trifluoro-meth-yl)benzoic acid.

Project description:The asymmetric unit of a second polymorph of the title compound, C(9)H(4)F(6)O(2), contains five independent mol-ecules, which form hydrogen-bonded O-H⋯O dimers about inversion centers. The most significant structural difference between this structure and that of the first polymorph [Tobin & Masuda (2009 ▶). Acta Cryst. E65, o1217] is the hydrogen-bonded, dimeric orientation of the carb-oxy-lic acid functionalities.

| S-EPMC3089103 | biostudies-literature

5-[(1H-Benzimidazol-1-yl)meth-yl]benzene-1,3-dicarb-oxy-lic acid.

Project description:Crystals of the title compound, C(16)H(12)N(2)O(4), were obtained accidentally from a hydro-thermal reaction of 5-[(1H-benzimidazol-1-yl)meth-yl]isophthalic acid with manganese bromide in the presence of N,N'-dimethyl-formamide. In the title mol-ecule, the benzimidazole ring system is almost planar, with a maximum deviation from the mean plane of 0.010 (2) Å. The benzimidazole and central benzene rings are inclined at a dihedral angle of 71.7 (6)°. The crystal structure is stabilized by O-H⋯N and O-H⋯O hydrogen bonds.

| S-EPMC3238952 | biostudies-literature

A third monoclinic polymorph of 3,4,5-trihy-droxy-benzoic acid monohydrate.

Project description:The title compound, C(7)H(6)O(5)·H(2)O, is a new polymorph of the structures reported by Jiang et al. (2000 ▶) [Acta Cryst. C56, 594-595] and Okabe et al. (2001 ▶) [Acta Cryst. E57, o764-o766]. The gallic acid mol-ecule is essentially planar (r.m.s. deviation = 0.550 Å). An intra-molecular O-H⋯O hydrogen bond occurs in the gallic acid mol-ecule, which is linked to the water mol-ecule by a further O-H⋯O hydrogen bond. In the crystal, the components are linked by O-H⋯O hydrogen bonds. The hydrogen-bonding pattern differs from those reported for the previous polymorphs.

| S-EPMC3120380 | biostudies-literature

A second monoclinic polymorph of N-(pyrazin-2-yl)aniline.

Project description:The two aromatic rings in the title compound, C(10)H(9)N(3), are aligned at 23.4 (1)° and the bridging C-N-C angle is 128.9 (1)°. In the crystal structure, intermolecular N-H⋯N hydrogen bonds result in a chain motif, the repeat distance of which is half the b axial length of 8.8851 (3) Å.

| S-EPMC2959673 | biostudies-literature

A second monoclinic polymorph of {2,6-bis[(2,4,5-trifluoro-phen-yl)imino-meth-yl]pyridine-κN,N',N''}dichloridonickel(II).

Project description:The asymmetric unit of the title compound, [NiCl(2)(C(19)H(9)F(6)N(3))], contains one half-mol-ecule residing on a crystallographic twofold rotation axis. The title compound crystallizes in space group C2/c while the previously reported polymorph was reported in P2(1)/c [Baldovino-Pantaleón et al. (2006 ▶). Adv. Synth. Catal.348, 236-242]. The Ni(2+) ion exhibits a penta-coordinate distorted trigonal-bipyramidal NiCl(2)N(3) geometry, with two Cl atoms in the equatorial plane. In the crystal, mol-ecules are linked by inter-molecular C-F⋯π [F⋯centroid = 2.9676 (14) Å] inter-actions.

| S-EPMC3274871 | biostudies-literature

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