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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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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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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.

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