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2-Amino-3-nitro-benzoic acid.

ABSTRACT: The title compound, C(7)H(6)N(2)O(4), is approximately planar (r.m.s. deviation = 0.026?Å for the 13 non-H atoms). The mol-ecular structure is stabilized by intra-molecular N-H?O hydrogen bonds, which generate S(6) ring motifs. In the crystal, mol-ecules are linked via inter-molecular N-H?O, O-H?O and C-H?O hydrogen bonds into a three-dimensional network.

SUBMITTER: Win YF

PROVIDER: S-EPMC3275235 | biostudies-literature | 2012 Feb

REPOSITORIES: biostudies-literature

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2-Amino-3-nitro-benzoic acid.

Win Yip-Foo YF Choong Chen-Shang CS Teoh Siang-Guan SG Quah Ching Kheng CK Fun Hoong-Kun HK

Acta crystallographica. Section E, Structure reports online 20120121 Pt 2

The title compound, C(7)H(6)N(2)O(4), is approximately planar (r.m.s. deviation = 0.026 Å for the 13 non-H atoms). The mol-ecular structure is stabilized by intra-molecular N-H⋯O hydrogen bonds, which generate S(6) ring motifs. In the crystal, mol-ecules are linked via inter-molecular N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds into a three-dimensional network. ...[more]

PMID: 22347091

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3-Amino-benzoic acid-4-nitro-benzoic acid (1/1).

Project description:In the title 1:1 adduct, C(7)H(5)NO(4)·C(7)H(7)NO(2), the nitro group of the 4-nitro benzoic acid is twisted from the attached ring by 4.40 (8)°. In the crystal, the mol-ecules are linked into ribbon-like structures along [150] and [10] via O-H⋯O, N-H⋯O, N-H⋯N and C-H⋯O inter-molecular hydrogen bonds.

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2-Methyl-amino-5-nitro-benzoic acid.

Project description:The title compound, C(8)H(8)N(2)O(4), is almost planar (r.m.s. deviation = 0.037?Å) and an intra-molecular N-H?O hydrogen bond generates an S(6) ring. In the crystal, inversion dimers linked by pairs of O-H?O hydrogen bonds generate R(2) (2)(8) loops. Inter-molecular N-H?O hydrogen bonds (involving the same H atom that forms the intra-molecular hydrogen bond) link the dimers into infinite sheets lying parallel to (102).

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4-Ethyl-amino-3-nitro-benzoic acid.

Project description:In the title compound, C(9)H(10)N(2)O(4), an intra-molecular N-H⋯O hydrogen-bond inter-action generates an S(6) ring motif. The nitro group is slightly twisted away from its attached benzene ring [dihedral angle = 15.29 (15)°]. In the crystal structure, mol-ecules are stacked down the a axis caused by short O⋯O(-1-x, -y, 2-z) contacts of 2.6481 (16) Å involving the O atoms of the nitro groups. The crystal packing is consolidated by inter-molecular O-H⋯O hydrogen bonds, linking the mol-ecules into centrosymmetric dimers.

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4-Butyl-amino-3-nitro-benzoic acid.

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4-Cyclo-butyl-amino-3-nitro-benzoic acid.

Project description:The asymmetric unit of the title compound, C(11)H(12)N(2)O(4), contains two crystallographically independent mol-ecules with similar geometries. Both mol-ecules contain an intra-molecular N-H?O hydrogen bond. The dihedral angles between the benzene ring and the mean plane of the cyclo-butane ring are 38.29?(7) and 57.04?(8)° in the two mol-ecules, and the nitro group is twisted slightly away from the plane of the benzene ring [dihedral angles = 9.15?(12) and 9.55?(12)° in the two mol-ecules]. In the crystal, the independent mol-ecules are linked into dimers by O-H?O hydrogen bonds between their carboxyl groups, and C-H?O and C-H?? inter-actions are formed between dimers.

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4-(sec-Butyl-amino)-3-nitro-benzoic acid.

Project description:The asymmetric unit of title compound, C(11)H(14)N(2)O(4), consists of two crystallographically independent mol-ecules (A and B). In each, intra-molecular N-H?O hydrogen bonds generate S(6) ring motifs. The mean plane of the nitro group forms dihedral angles of 4.5?(3) and 0.5?(3)° with the benzene ring in mol-ecules A and B, respectively. In mol-ecule A, there is disorder of the butyl-amino group which corresponds to an approximate 180° rotation about the N-C(H) bond, forming two sites with refined occupancies of 0.722?(6) and 0.278?(6). Mol-ecule B is similarly disordered but in addition there is further rotational disorder about the C(H)-C(H(2)) bond giving a ratio of occupancies for three components of 0.42:0.35:0.23. In the crystal structure, inter-molecular O-H?O hydrogen bonds link mol-ecules into centrosymmetric dimers generating R(2) (2)(8) ring motifs. The crystal structure is also stabilized by weak inter-molecular C-H?O inter-actions.

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4-tert-Butyl-amino-3-nitro-benzoic acid.

Project description:In the title compound, C(11)H(14)N(2)O(4), all non-H atoms lie in a mirror plane except for one of the methyl groups which deviates from the mirror plane by 0.919?(3)?Å and is twisted by a torsion angle of 62.9?(2)°. An intra-molecular N-H?O hydrogen bond generates an S(6) ring motif. In the crystal packing, the mol-ecules are linked together by O-H?O hydrogen bonds, forming dimers with graph-set motif R(2) (2)(8) which propagate along the a-axis direction. C-H?O contacts link adjacent dimers with a graph-set motif C(2) (2)(7), forming chains along b, and further consolidate the structure into a three-dimensional network. The crystal packing is further strengthened by short inter-molecular O?O=C [2.655?(4)?Å] contacts.

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2-Amino-5-nitro-benzoic acid.

Project description:In the title compound, C(7)H(6)N(2)O(4), an intra-molecular N-H?O hydrogen bond generates an S(6) ring. In the crystal, inversion dimers linked by pairs of O-H?O hydrogen bonds generate R(2) (2)(8) loops. Inter-molecular N-H?O and C-H?O hydrogen bonds then link the dimers, generating R(3) (3)(16)R(2) (1)(6) motifs. The whole mol-ecule is essentially planar, with the greatest deviation from the mean plane being 0.065?(2)?Å.

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4-Amino-pyridinium 4-nitro-benzoate 4-nitro-benzoic acid.

Project description:The asymmetric unit of the title compound, C(5)H(7)N(2) (+)·C(7)H(4)NO(4) (-)·C(7)H(5)NO(4), consists of an amino-pyridinium cation, a 4-nitro-benzoate anion and a neutral 4-nitro-benzoic acid mol-ecule. The pyridine ring forms dihedral angles of 64.70?(5)° and 70.37?(5)°, respectively, with the benzene rings of 4-nitro-benzoic acid and 4-nitro-benzoate. In the crystal structure, the cations, anions and the neutral 4-nitro-benzoic acid mol-ecules are linked by O-H?O and N-H?O hydrogen bonds, forming a two-dimensional network parallel to (001). Adjacent networks are cross-linked via C-H?O hydrogen bonds and ?-? stacking inter-actions [centroid-centroid distances 3.6339?(6) and 3.6566?(6)?Å].

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Isolation of 3-amino-4-nitro-benzyl acetate: evidence of an undisclosed impurity in 5-amino-2-nitro-benzoic acid.

Project description:Yellow crystals of the title compound 3-amino-4-nitro-benzyl acetate, C9H10N2O4, were isolated from the reaction of acetic anhydride with (5-amino-2-nitro-phen-yl)methanol, prepared from reduction of commerically available 5-amino-2-nitro-benzoic acid with borane-THF. The mol-ecule is essentially planar (r.m.s. deviation = 0.028 Å). The mol-ecules are linked by inter-molecular N-H⋯O hydrogen-bonding inter-actions between the carbonyl and amine groups, forming a zigzag chain along the b-axis direction lying in a plane parallel to (-102). The chains are stacked along the c axis by π-π inter-actions [centroid-centroid distances = 3.6240 (3) and 3.5855 (4) Å]. A strong intra-molecular N-H⋯O hydrogen-bonding inter-action is observed between the nitro group and the amine group [2.660 (2) Å].

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