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Crystal structure of a new monoclinic polymorph of N-(4-methyl-phen-yl)-3-nitro-pyridin-2-amine.

ABSTRACT: The title compound, C12H11N3O2, is a second monoclinic polymorph (P21, with Z' = 4) of the previously reported monoclinic (P21/c, with Z' = 2) form [Akhmad Aznan et al. (2010 ?). Acta Cryst. E66, o2400]. Four independent mol-ecules comprise the asymmetric unit, which have the common features of a syn disposition of the pyridine N atom and the toluene ring, and an intra-molecular amine-nitro N-H?O hydrogen bond. The differences between mol-ecules relate to the dihedral angles between the rings which range from 2.92?(19) to 26.24?(19)°. The geometry-optimized structure [B3LYP level of theory and 6-311?g+(d,p) basis set] has the same features except that the entire mol-ecule is planar. In the crystal, the three-dimensional architecture is consolidated by a combination of C-H?O, C-H??, nitro-N-O?? and ?-? inter-actions [inter-centroid distances = 3.649?(2)-3.916?(2)?Å].

SUBMITTER: Aznan AM

PROVIDER: S-EPMC4158497 | biostudies-literature | 2014 Aug

REPOSITORIES: biostudies-literature

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Crystal structure of a new monoclinic polymorph of N-(4-methyl-phen-yl)-3-nitro-pyridin-2-amine.

Aznan Aina Mardia Akhmad AM Abdullah Zanariah Z Lee Vannajan Sanghiran VS Tiekink Edward R T ER

Acta crystallographica. Section E, Structure reports online 20140719 Pt 8

The title compound, C12H11N3O2, is a second monoclinic polymorph (P21, with Z' = 4) of the previously reported monoclinic (P21/c, with Z' = 2) form [Akhmad Aznan et al. (2010 ▶). Acta Cryst. E66, o2400]. Four independent mol-ecules comprise the asymmetric unit, which have the common features of a syn disposition of the pyridine N atom and the toluene ring, and an intra-molecular amine-nitro N-H⋯O hydrogen bond. The differences between mol-ecules relate to the dihedral angles between the rings wh ...[more]

PMID: 25249854

Similar Datasets

N-(4-Methyl-phen-yl)-3-nitro-pyridin-2-amine.

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| S-EPMC3008084 | biostudies-literature

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Project description:The title compound, C(12)H(10)N(2)O, a second monoclinic poly-morph of (E)-phen-yl(pyridin-2-yl)methanone oxime crystallizes in the space group P2(1)/n (Z = 4). The previously reported polymorph [Taga et al. (1990 ▶). Acta Cryst. C46, 2241-2243] occurs in the space group C2/c (Z = 8). In the crystal, pairs of bifurcated O-H⋯(N,O) hydrogen bonds link the mol-ecules into inversion dimers. The dimers are linked by C-H⋯π inter-actions, forming a linear arrangement. The dihedral angle between the pyridine and phenyl rings is 67.70 (8)°.

| S-EPMC3569829 | biostudies-literature

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| S-EPMC4647416 | biostudies-literature

Crystal structure of (pyridin-2-yl-methyl-idene)(tri-phenyl-meth-yl)amine.

Project description:The title Schiff base compound, C25H20N2, crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. In both mol-ecules, the imine group is approximately coplanar with the pyridine ring, with N-C-C-N torsion angles of 170.1?(3) and -172.0?(3)?Å. In the crystal, A and B dimers are linked by pairs of C-H?? inter-actions and further C-H?? bonds link the dimers into a three-dimensional network.

| S-EPMC4257176 | biostudies-literature

4-Methyl-N-(3-methyl-phen-yl)pyridin-2-amine.

Project description:The title amine, C(13)H(14)N(2), is twisted with a dihedral angle between the rings of 60.07?(9)°. The amine N-H group and pyridine N atom are syn allowing for the formation of centrosymmetric eight-membered {?HNCN}(2) synthons via N-H?N hydrogen bonds. The two-mol-ecule aggregates are sustained in the three-dimensional crystal packing via C-H?? and ?-? inter-actions [centroid-centroid distance for pyridyl rings = 3.7535?(12)?Å].

| S-EPMC3247467 | biostudies-literature

N-(3-Chloro-phen-yl)-3-nitro-pyridin-2-amine.

Project description:The dihedral angle between the benzene and pyridyl rings in the title compound, C(11)H(8)ClN(3)O(2), is 22.65?(10)°, indicating a twisted mol-ecule. The amine H and nitro O atoms form a donor-acceptor pair for an intra-molecular N-H?O hydrogen bond so that the nitro group is almost coplanar with the pyridine ring to which it is connected [O-N-C-C torsion angle = 7.4?(3)°]. The pyridine N and Cl atoms are approximately syn. The crystal packing features C-H?Cl inter-actions that lead to undulating supra-molecular chains along [101]. These are connected into sheets by ?-? inter-actions occurring between the benzene rings and between the pyridine rings of translationally related mol-ecules along the b axis [centroid-centroid distances = length of b axis = 3.7157?(2)?Å].

| S-EPMC3247465 | biostudies-literature

Crystal structure of 4-nitro-N-[(pyridin-2-yl)methyl-idene]aniline.

Project description:The title compound, C12H9N3O2, adopts an E conformation at the imine double bond. The pyridyl ring makes a dihedral angle of 47.78 (5)° with the benzene ring, indicating the mol-ecule is twisted. In the crystal, mol-ecules are π-π stacked into columns parallel to [100], with an inter-planar separation of 3.8537 (8) Å, corresponding to the length of the a axis. The chains are further linked via weak C-H⋯O and C-H⋯N hydrogen bonds, forming two-dimensional sheets parallel to (010). The sheets interact by van der Waals inter-actions.

| S-EPMC4647417 | biostudies-literature

Crystal structure of 5,15-bis-(4-methyl-phen-yl)-10,20-bis-(4-nitro-phen-yl)porphyrin nitro-benzene disolvate.

Project description:The whole mol-ecule of the title porphyrin, C46H32N6O4·2C6H5NO2, which crystallized as a nitro-benzene disolvate, is generated by inversion symmetry. The porphyrin macrocycle is almost planar, the maximum deviation from the mean plane of the non-hydrogen atoms is 0.097 (2) Å. The aryl rings at the meso positions are inclined to this mean plane by 74.84 (6)° for the nitro-phenyl rings and 73.37 (7)° for the tolyl rings. In the crystal, the porphyrin mol-ecules are linked by C-H⋯O hydrogen bonds, forming chains along [100]. The solvent mol-ecules are also linked by C-H⋯O hydrogen bonds, forming chains along [100]. Inter-digitation of the p-tolyl groups along the c axis creates rectangular channels in which the solvent mol-ecules are located.

| S-EPMC5778485 | biostudies-literature

1-Nitro-4-(4-nitro-phen-oxy)benzene: a second monoclinic polymorph.

Project description:In the title compound, C12H8N2O5, the aromatic rings are inclined to one another by 56.14?(7)°. The nitro groups are inclined by to the benzene rings to which they are attached by 3.86?(17) and 9.65?(15)°. In the crystal, mol-ecules are linked by C-H?O hydrogen bonds, forming a three-dimensional structure. The title compound is a new monoclinic polymorph, crystallizing in space group P21/c. The first polymorph crystallized in space group C2/c and the mol-ecule possesses twofold rotation symmetry. Two low-temperature structures of this polymorph (150?K and 100?K, respectively) have been reported [Meciarova et al. (2004). Private Communication (refcode IXOGAD). CCDC, Cambridge, England, and Dey & Desiraju (2005). Chem. Commun. pp. 2486-2488].

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2-{[3-Methyl-4-(2,2,2-trifluoro-eth-oxy)pyridin-2-yl]methyl-sulfan-yl}-1H-benzimidazole monohydrate: a monoclinic polymorph.

Project description:The title compound, C(16)H(14)F(3)N(3)OS·H(2)O, which had been previously characterized in the space group P-1 [Ren et al. (2011 ?). Acta Cryst. E67, o270], has now been crystallized from 1-propanol in the monoclinic form in the space group P2(1)/c. While the triclinic form is a Z' = 2 crystal, the new monoclinic polymorph includes one main mol-ecule and one water lattice mol-ecule in the asymmetric unit. In the crystal, the water mol-ecule is sandwiched between neighboring main mol-ecules and behaves as both donor and acceptor in O-H?N and N-H?O hydrogen bonds with the imidazole N atoms. This pattern of chains parallel to [100] further inter-acts via O-H?N(pyridine) contacts.

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