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Redetermination of pyridine-4-carbonitrile-chloranilic acid (1/1) at 180 K.

ABSTRACT: In the crystal structure of the title compound, C(6)H(4)N(2)·C(6)H(2)Cl(2)O(4), two chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydr-oxy-1,4-benzoquinone) mol-ecules are connected by O-H?O hydrogen bonds to form a dimeric unit. The pyridine-4-carbonitrile mol-ecules are linked on both sides of the dimer via N?H?O hydrogen bonds to give a centrosymmetric 2:2 complex of pyridine-4-carbonitrile and chloranilic acid. The H atom in the N?H?O hydrogen bond is disordered over two positions with approximately equal occupancies. The pyridine ring makes a dihedral angle of 61.54?(14)° with the chloranilic acid plane. The 2:2 units are further linked by inter-molecular C-H?O and C-H?Cl hydrogen bonds. This determination presents a siginficantly higher precision crystal structure than the previously published structure [Tomura & Yamasshita (2008 ?). X-ray Struct. Anal. Online, 24, x31-x32].

SUBMITTER: Gotoh K

PROVIDER: S-EPMC2961658 | biostudies-literature | 2008 Jun

REPOSITORIES: biostudies-literature

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Redetermination of pyridine-4-carbonitrile-chloranilic acid (1/1) at 180 K.

Gotoh Kazuma K Nagoshi Hirokazu H Ishida Hiroyuki H

Acta crystallographica. Section E, Structure reports online 20080613 Pt 7

In the crystal structure of the title compound, C(6)H(4)N(2)·C(6)H(2)Cl(2)O(4), two chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydr-oxy-1,4-benzoquinone) mol-ecules are connected by O-H⋯O hydrogen bonds to form a dimeric unit. The pyridine-4-carbonitrile mol-ecules are linked on both sides of the dimer via N⋯H⋯O hydrogen bonds to give a centrosymmetric 2:2 complex of pyridine-4-carbonitrile and chloranilic acid. The H atom in the N⋯H⋯O hydrogen bond is disordered over two positions wi ...[more]

PMID: 21202894

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Pyridine-3-carbonitrile-chloranilic acid-acetonitrile (2/1/2).

Project description:In the crystal structure of the title compound, 2C(6)H(4)N(2)·C(6)H(2)Cl(2)O(4)·2C(2)H(3)N, the two symmetry-related pyridine-3-carbonitrile mol-ecules are linked to either side of a chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydr-oxy-1,4-benzoquinone) mol-ecule via inter-molecular O-H?N hydrogen bonds, giving a centrosymmetric 2:1 unit. The dihedral angle between the pyridine ring and the chloranilic acid plane is 26.71?(6)°. In addition, the two acetonitrile mol-ecules are linked to either side of the 2:1 unit through C-H?N hydrogen bonds, forming a 2:1:2 aggregate. These 2:1:2 aggregates are further linked by weak inter-molecular C-H?N and C-H?O hydrogen bonds, forming a tape along the c axis.

| S-EPMC2970440 | biostudies-other

Chloranilic acid: a redetermination at 100?K.

Project description:The crystal structure of chloranilic acid, C(6)H(2)Cl(2)O(4), was first described by Andersen in 1967 [Andersen, E. K. (1967). Acta Cryst. 22, 188-191] at room temperature using visually estimated intensities. Taking into account the importance of the title compound, we have redetermined the structure at 100?(1)?K. The approximately planar mol-ecule [the maximum deviation from the mean plane through the ring is 0.0014?(9)?Å for the ring atoms and 0.029?(3)?Å for the other atoms] occupies a special position, lying across the center of symmetry. In the crystal structure, a two-dimensional hydrogen-bonded network sustained by O-H?O inter-actions runs approximately parallel to [101]. The two-dimensional layers are further packed in a parallel fashion, stabilized by Cl?Cl inter-actions [Cl?Cl = 3.2838?(8)?Å, C-Cl?Cl = 152.96?(6)°].

| S-EPMC2979702 | biostudies-literature

Oxalic acid-pyridine-4-carbonitrile (1/2).

Project description:In the title compound, 2C(6)H(4)N(2)·C(2)H(2)O(4), the oxalic acid mol-ecule lies about an inversion center. The pyridine ring of the pyridine-4-carbonitrile mol-ecule is almost planar, the largest deviation from the least-squares plane being 0.006?(1)?Å; the nitrile N atom deviates from this plane by 0.114?(1)?Å. In the crystal, the oxalic acid mol-ecules and the pyridine-4-carbonitrile mol-ecules form stacks. Neighboring mol-ecules within the stacks are related by translation in the a direction, with inter-planar distances of 3.183?(1) and 3.331?(2)?Å, respectively. Each oxalic acid mol-ecule forms strong O-H?N hydrogen bonds with two mol-ecules of pyridine-4-carbonitrile. Besides this, there are also weak C-H?O inter-actions.

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Gabapentin-lactum-chloranilic acid (1/1).

Project description:In the title compound, C(9)H(15)NO·C(6)H(2)Cl(2)O(4) [sytematic name: 2-aza-spiro-[4.5]decan-3-one-chloranilic acid (1/1)], the cyclo-hexane ring of the lactam molecule adopts a slightly distorted normal chair conformation and the five-membered 3-aza-spiro ring is in a slightly distorted chair conformation. The dihedral angle between the least-squares planes of the cyclohexane and 3-azaspiro rings is 84.0?(3)°. In the crystal, the chloranilic acid mol-ecule and the gabapentin-lactum mol-ecules are held together by strong inter-molecular N-H?O and O-H?O hydrogen bonds with two bifurcated O acceptor atoms on the chloranilic acid mol-ecule and one on the gabapentin-lactum mol-ecule, each bonding with an inter- and intra-molecular hydrogen bond. The molecules are linked into chains parallel to (011) and propagating along the b axis.

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Dibromidobis(pyridine-3-carbonitrile-?N)zinc(II).

Project description:In the title compound, [ZnBr(2)(C(6)H(4)N(2))(2)], the Zn(II) atom is four coordinated in a slightly distorted tetra-hedral fashion by two pyridine N atoms and two Br(-) anions. ?-? inter-actions between adjacent pyridine rings [centroid-centroid distance = 3.6229?(19)?Å] are the main factor controlling the packing and are effective in the stabilization of the crystal structure.

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Dibromidobis(pyridine-3-carbonitrile-?N)mercury(II).

Project description:In the crystal structure of the title compound, [HgBr(2)(C(6)H(4)N(2))(2)], the Hg atom is four coordinated by two pyridine N atoms and two Br(-) anions in a considerably distorted tetrahedral environment. ?-? inter-actions between adjacent pyridine rings [centroid-centroid distance of 3.648?(3)?Å] stabilize the crystal structure.

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Redetermination of 4-cyano-pyridine N-oxide.

Project description:In the title pyridine N-oxide derivative, C(6)H(4)N(2)O, the 4-cyano substituent almost lies in the mean plane of the pyridine ring (r.m.s deviation of all non-H atoms = 0.004 Å). This redetermination results in a crystal structure with significantly higher precision [N-O bond length is 1.2997 (15) compared with 1.303 (5) Å in the original] than the original determination, which was recorded using the multiple-film technique and visually estimated intensities [Hardcastle et al. (1974 ▶). J. Cryst. Mol. Struct.4, 305-311]. The crystal structure features weak C-H⋯O and C-H⋯N inter-actions, which lead to the formation of chains that inter-sect each other parallel to (001).

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Redetermination at 180?K of a layered lanthanide-organic framework.

Project description:The asymmetric unit of the title compound, poly[(?(4)-{[bis-(hydrogen phospho-natometh-yl)aza-nium-yl]meth-yl}phospho-nato)lanthanum(III)], [La(C(3)H(9)NO(9)P(3))](n), comprises an La(3+) center and a H(3)nmp(3-) anion (where H(3)nmp(3-) is a residue of partially deprotonated nitrilo-tris-(methyl-ene-phospho-nic acid), namely {[bis-(hydrogen phospho-natometh-yl)aza-nium-yl]meth-yl}-phos-pho-nate). This study concerns a structural redetermination using single-crystal X-ray diffraction data, collected at the low temperature of 180?K, of a recently investigated material whose structural details have been proposed from powder X-ray diffraction studies [Silva et al. (2011 ?). J. Am. Chem. Soc.133, 15120-15138]. The main difference between the two models rests on the position of the H atoms. While two H atoms were modeled as attached to the same phospho-nate group in the powder determination, in the current model, the same H atoms are instead distributed among two of these groups. The sample studied was an inversion twin.

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Crystal structures of two 1:2 dihydrate compounds of chloranilic acid with 2-carb-oxy-pyridine and 2-carb-oxy-quinoline.

Project description:The crystal structure of the 1:2 dihydrate compound of chloranilic acid (systematic name: 2,5-di-chloro-3,6-dihy-droxy-1,4-benzo-quinone) with 2-carb-oxy-pyridine (another common name: picolinic acid; systematic name: pyridine-2-carb-oxy-lic acid), namely, 2C6H5.5NO20.5+·C6HCl2O4-·2H2O, (I), has been determined at 180?K, and the structure of the 1:2 dihydrate compound of chloranilic acid with 2-carb-oxy-quinoline (another common name: quinaldic acid; systematic name: quinoline-2-carb-oxy-lic acid), namely, 2C10H7NO2·C6H2Cl2O4·2H2O, (II), has been redetermined at 200?K. This determination presents a higher precision crystal structure than the previously published structure [Marfo-Owusu & Thompson (2014 ?). X-ray Struct. Anal. Online, 30, 55-56]. Compound (I) was analysed as a disordered structure over two states, viz. salt and co-crystal. The salt is bis-(2-carb-oxy-pyridinium) chloranilate dihydrate, 2C6H6NO2+·C6Cl2O42-·2H2O, and the co-crystal is bis-(pyridinium-2-carboxyl-ate) chloranilic acid dihydrate, 2C6H5NO2·C6H2Cl2O4·2H2O, including zwitterionic 2-carb-oxy-pyridine. In both salt and co-crystal, the water mol-ecule links the chloranilic acid and 2-carb-oxy-pyridine mol-ecules through O-H?O and N-H?O hydrogen bonds. The 2-carb-oxy-pyridine mol-ecules are connected into a head-to-head inversion dimer by a short O-H?O hydrogen bond, in which the H atom is disordered over two positions. Compound (II) is a 1:2 dihydrate co-crystal of chloranilic acid and zwitterionic 2-carb-oxy-quinoline. The water mol-ecule links the chloranilic acid and 2-carb-oxy-quinoline mol-ecules through O-H?O hydrogen bonds. The 2-carb-oxy-quinoline mol-ecules are connected into a head-to-tail inversion dimer by a pair of N-H?O hydrogen bonds.

| S-EPMC5730236 | biostudies-literature

Crystal structures of three hydrogen-bonded 1:2 compounds of chloranilic acid with 2-pyridone, 3-hy-droxy-pyridine and 4-hyroxypyridine.

Project description:The crystal structures of the 1:2 compounds of chloranilic acid (systematic name: 2,5-di-chloro-3,6-dihy-droxy-1,4-benzo-quinone) with 2-pyridone, 3-hy-droxy-pyridine and 4-hyroxypyridine, namely, bis-(2-pyridone) chloranilic acid, 2C5H5NO·C6H2Cl2O4, (I), bis-(3-hy-droxy-pyridinium) chloranilate, 2C5H6NO+·C6Cl2O42-, (II), and bis-(4-hy-droxy-pyridinium) chloranilate, 2C5H6NO+·C6Cl2O42-, (III), have been determined at 120?K. In the crystal of (I), the base mol-ecule is in the lactam form and no acid-base inter-action involving H-atom transfer is observed. The acid mol-ecule lies on an inversion centre and the asymmetric unit consists of one half-mol-ecule of chloranilic acid and one 2-pyridone mol-ecule, which are linked via a short O-H?O hydrogen bond. 2-Pyridone mol-ecules form a head-to-head dimer via a pair of N-H?O hydrogen bonds, resulting in a tape structure along [201]. In the crystals of (II) and (III), acid-base inter-actions involving H-atom transfer are observed and the divalent cations lie on an inversion centre. The asymmetric unit of (II) consists of one half of a chloranilate anion and one 3-hy-droxy-pyridinium cation, while that of (III) comprises two independent halves of anions and two 4-hy-droxy-pyridinium cations. The primary inter-molecular inter-action in (II) is a bifurcated O-H?(O,O) hydrogen bond between the cation and the anion. The hydrogen-bonded units are further linked via N-H?O hydrogen bonds, forming a layer parallel to the bc plane. In (III), one anion is surrounded by four cations via O-H?O and C-H?O hydrogen bonds, while the other is surrounded by four cations via N-H?O and C-H?Cl hydrogen bonds. These inter-actions link the cations and the anions into a layer parallel to (301).

| S-EPMC5730315 | biostudies-literature

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