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

ABSTRACT: 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].

SUBMITTER: Kuai HW

PROVIDER: S-EPMC3515175 | biostudies-literature | 2012 Nov

REPOSITORIES: biostudies-literature

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

Kuai Hai-Wei HW

Acta crystallographica. Section E, Structure reports online 20121006 Pt 11

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 ...[more]

PMID: 23284402

Similar Datasets

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

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

Project description: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.

| S-EPMC3238873 | biostudies-literature

A monoclinic polymorph of 1,3-bis-(2-pyridylamino-meth-yl)benzene.

Project description:The mol-ecules of the title compound, C(18)H(18)N(4), are linked by two different N-H⋯N(pyrid-yl) hydrogen bonds into a linear chain.

| S-EPMC2915309 | biostudies-literature

Naphthalene-1,8-dicarb-oxy-lic anhydride: a monoclinic polymorph.

Project description:A new type of naphthalene-1,8-dicarb-oxy-lic anhydride, C(12)H(6)O(3), was synthesized hydro-thermally. Unlike the two previously reported polymorphs, which crystallize in the ortho-rhom-bic space groups P2(1)2(1)2(1) [Shok et al. (1971). Kristallografiya, 16, 500-502; Grigor'eva & Chetkina (1975). Kristallografiya, 20, 1289-1290] and Pbca [Shok & Gol'der (1970). Zh. Strukt. Khim.11, 939-940], this present structure crystallizes in the monoclinic space group P2(1)/c. In this structure, the planar [total puckering amplitude Q = 0.0362 (15)] mol-ecules lie parallel to each other along the a axis.

| S-EPMC2983304 | biostudies-literature

2-[3-(1H-Benzimidazol-2-yl)prop-yl]-1H-benzimidazol-3-ium 3,5-dicarb-oxy-benzoate-benzene-1,3,5-tricarb-oxy-lic acid-water (1/1/1).

Project description:The title compound, C(17)H(17)N(4) (+)·C(9)H(5)O(6) (-)·C(9)H(6)O(6)·H(2)O, contains a protonated 2,2'-(1,3-propanedi-yl)bis-(1H-benzimidazole) cation, a deprotonated benzene-1,3,5-tricarb-oxy-lic acid anion, a neutral benzene-1,3,5-tricarb-oxy-lic acid mol-ecule and a water mol-ecule, which are linked together through N-H?O, O-H?O and weak C-H?O hydrogen bonds into almost double sheets parallel to (4). These hydrogen-bonded sheets are packed in the crystal with the formation of centrosymmetric voids of 25.5?Å(3), which are filled by the water mol-ecules.

| S-EPMC3009361 | biostudies-literature

2-[(1H-Benzimidazol-1-yl)meth-yl]phenol benzene hemisolvate.

Project description:In the title solvate, C14H12N2O·0.5C6H6, the complete benzene molecule is generated by a crystallographic inversion centre. The dihedral angle between the planes of the benzimidazole moiety and the phenol substituent is 75.28 (3)°. In the crystal, O-H⋯N hydrogen bonds link the mol-ecules into parallel chains propagating along [100]. The mol-ecules are further connected by C-H⋯π inter-actions.

| S-EPMC3998331 | biostudies-literature

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

Benzene-1,3-dicarb-oxy-lic acid-1,2-bis-(4-pyrid-yl)ethene (1/1).

Project description:In the title compound, C(12)H(10)N(2)·C(8)H(6)O(4), the asymmetric unit contains two halves of 1,2-bis-(4-pyrid-yl)ethene (bpe) mol-ecules and one benzene-1,3-dicarb-oxy-lic acid (1,3-H(2)BDC) mol-ecule. These bpe and 1,3-H(2)BDC mol-ecules are linked by classical O-H?N hydrogen bonds, forming an extended one-dimensional zigzag chain. Each chain is further linked with neighboring ones by ?-? inter-actions between the pyridine and aromatic rings [centroid-centroid distances = 3.9306?(15)?Å] and the pyridine rings of pairs of symmetry-related mol-ecules [centroid-centroid distances = 3.5751?(15), 3.7350?(15) and 3.6882?(15)?Å], with the formation of a three-dimensional supra-molecular framework.

| S-EPMC3247433 | 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

2-[(1,3-Benzo-thia-zol-2-yl)imino-meth-yl]-6-meth-oxy-phenol: a new monoclinic polymorph.

Project description:The title compound, C15H12N2O2S, is a P21/c polymorph of a previously reported P21/n polymorph [Büyükgüngör et al. (2004 ?). Acta Cryst. E60, o1414-o1416]. The dihedral angle between the benzo-thia-zole (r.m.s. deviation = 0.010?Å) and the benzene ring of 7.86?(6)° compares with 10.76?(10)° in the literature structure. The meth-oxy substituent is almost coplanar with the benzene ring to which it is attached [C-O-C-C torsion angle = 178.31?(14)°] and the conformation about the imine bond [1.287?(2)?Å] is E. There is an intra-molecular O-H?N hydrogen bond and the hy-droxy O and thio-ether S atoms are syn. In the crystal, columns are formed along the b axis as centrosymmetric dimeric aggregates, mediated by C-H?O inter-actions and linked by ?-? inter-actions between the thia-zole and benzene rings [centroid-to-centroid distance = 3.8256?(10)?Å].

| S-EPMC3793768 | biostudies-literature

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