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N-[(3RS,4SR)-1-Benzyl-4-methyl-piperi-din-3-yl]-1-(4-methylphenyl-sulfonyl)-5-nitro-1H-pyrrolo-[2,3-b]pyridin-4-amine.

ABSTRACT: The structure of the title compound, C(27)H(29)N(5)O(4)S, displays an intra-molecular N-H?O hydrogen bond. The pyrrolo-[2,3-b]pyridine core makes a dihedral angle of 85.5?(4)° with the benzyl residue and a dihedral angle of 89.4?(9)° with the tosyl ring. The nitro group is slightly twisted out of the plane of the planar pyrrolo-pyridine system [(-N-)C-C-N-O torsion angle = -4.61?(18)° and (-NH-)C-C-N-O = -6.46?(18)°].

SUBMITTER: Pfaffenrot E

PROVIDER: S-EPMC3470359 | biostudies-literature | 2012 Oct

REPOSITORIES: biostudies-literature

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N-[(3RS,4SR)-1-Benzyl-4-methyl-piperi-din-3-yl]-1-(4-methylphenyl-sulfonyl)-5-nitro-1H-pyrrolo-[2,3-b]pyridin-4-amine.

Pfaffenrot Ellen E Schollmeyer Dieter D Laufer Stefan S

Acta crystallographica. Section E, Structure reports online 20120926 Pt 10

The structure of the title compound, C(27)H(29)N(5)O(4)S, displays an intra-molecular N-H⋯O hydrogen bond. The pyrrolo-[2,3-b]pyridine core makes a dihedral angle of 85.5 (4)° with the benzyl residue and a dihedral angle of 89.4 (9)° with the tosyl ring. The nitro group is slightly twisted out of the plane of the planar pyrrolo-pyridine system [(-N-)C-C-N-O torsion angle = -4.61 (18)° and (-NH-)C-C-N-O = -6.46 (18)°]. ...[more]

PMID: 23125772

Similar Datasets

N-[(3RS,4RS)-1-Benzyl-4-methyl-piperidin-3-yl]-5-nitro-1-phenyl-sulfonyl-1H-pyrrolo-[2,3-b]pyridine-4-amine.

Project description:The pyrrolo-pyridine system in the title compound, C(27)H(29)N(5)O(4)S, is oriented at a dihedral angle of 71.20?(5)° towards the phenyl ring of the tosyl residue and at a dihedral angle of 45.43?(4)° towards the benzyl group. The structure shows an intra-molecular N-H?O and a weak intra-molecular N-H?N hydrogen bond. The piperidine ring adopts a chair conformation, with the cis substituents displaying a torsion angle of -54.59?(18)°.

| S-EPMC3470400 | biostudies-literature

1-[(3RS,4RS)-1-Benzyl-4-methyl-piperi-din-3-yl]-1,6-dihydro-imidazo[4,5-d]pyrrolo-[2,3-b]pyridine hemihydrate.

Project description:The benzyl residue in the title compound, C(21)H(23)N(5)·0.5H(2)O, is oriented at a dihedral angle of 83.8?(3)° towards the 1,6-dihydro-imidazo[4,5-d]pyrrolo-[2,3-b]pyridine system. The piperidine ring adopts a chair conformation with the cis substituents displaying a torsion angle of -45.91?(16)°. In the crystal, mol-ecules are accumulated as racemic dimers by two inter-molecular hydrogen bonds between the pyrrolo-pyridine systems. Another hydrogen bond is formed between the imidazole ring and the cocrystallized water mol-ecule, which is located on a twofold rotation axis.

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4-Methyl-3-nitro-pyridin-2-amine.

Project description:In the title compound, C(6)H(7)N(3)O(2), the dihedral angle between the nitro group and the pyridine ring is 15.5?(3)° and an intra-molecular N-H?O hydrogen bond occurs. In the crystal, inversion dimers linked by two N-H?N hydrogen bonds occur, resulting in R(2) (2)(8) rings. The packing is stabilized by aromatic ?-? stacking [centroid-centroid distance = 3.5666?(15)?Å] and a short N-O?? contact is seen.

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2-Chloro-5-nitro-pyridin-4-amine.

Project description:The title mol-ecule, C(5)H(4)ClN(3)O(2), possesses mirror symmetry, with all of the atoms lying in the mirror plane. There is an intra-molecular N-H⋯O hydrogen bond involving the adjacent -NO(2) and -NH(2) groups. A short C-H⋯O inter-action is also observed. In the crystal, adjacent mol-ecules are linked via N-H⋯Cl and N-H⋯N hydrogen bonds, forming chains propagating along [100].

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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

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

Project description:Two independent mol-ecules comprise the asymmetric unit of the title compound, C(12)H(11)N(3)O(2). These differ in terms of the relative orientations of the benzene rings as seen in the respective dihedral angles formed between the pyridine and benzene rings [17.42 (16) and 34.64 (16)°]. Both mol-ecules are twisted about the amine-tolyl N-C bonds [respective torsion angles = 22.3 (5) and 35.9 (5)°] but only about the amine-pyridine N-C bond in the first independent mol-ecule [respective torsion angles = -11.7 (5) and 0.8 (5)°]. Intra-molecular N-H⋯O hydrogen bonds preclude the amine H atoms from forming significant inter-molecular inter-actions. The crystal packing features inter-molecular C-H⋯O and C-H⋯π and π-π [centroid-centroid distance: pyridine-benzene = 3.6442 (19) Å and pyridine-pyridine = 3.722 (2) Å] contacts.

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

Project description:There are two mol-ecules in the asymmetric unit mol-ecule of the title compound, C(8)H(10)ClN(3)O(2). Intra-molecular N-H?O hydrogen bonds stabilize the mol-ecular structure. There are no classical inter-molecular hydrogen bonds in the crystal structure.

| S-EPMC3120349 | biostudies-literature

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

Project description:In the title compound, C(11)H(8)ClN(3)O(2), the presence of intra-molecular N-H?O and C-H?N inter-actions help to establish an almost planar mol-ecule [dihedral angle between the pyridine and benzene rings = 9.89?(8)° and r.m.s. deviation for all 17 non-H atoms = 0.120?Å]. Supra-molecular tapes feature in the crystal packing whereby dimeric aggregates sustained by pairs of C-H?O inter-actions are connected by ?-? inter-actions occurring between translationally related pyridine rings and between translationally related benzene rings along the b axis [centroid-centroid distance = length of b axis = 3.8032?(4)?Å].

| S-EPMC3238847 | biostudies-other

(3RS,4SR)-Methyl 4-(2-chloro-5,8-di-methoxy-quinolin-3-yl)-1-phenyl-pyrrolidine-3-carboxyl-ate.

Project description:The mol-ecule of the title compound, C(23)H(23)ClN(2)O(4), contains a quinolyl unit linked to a functionalized pyrrolidine system with a 3,4-trans arrangement of the substituents. The unit cell contains two stereoisomers that have the absolute stereochemistry 3S,4R and 3R,4S. The pyrrolidine ring adopts a twist conformation with pseudo-rotation parameters P = 258.2 (3)° and τ(M) = 35.3 (1)°. The packing is stabilized by C-H⋯π inter-actions and offset π-π stacking (centroid-to-centroid distance = 3.849 Å, inter-planar distance = 3.293 Å and slippage = 1.994 Å) between phenyl rings, leading to a two-dimensional network.

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(3RS)-S-[1-(3-Chloro-phen-yl)-2-oxopyr-roli-din-3-yl]thio-uronium bromide.

Project description:In the title molecular salt, C(11)H(13)ClN(3)OS(+)·Br(-), the C-N bond lengths in the -S-C(NH(2))(2) fragment indicate partial double-bond character of these bonds. The constituent ions are connected by N-H?Br bridges into Z-shaped chains. The supra-molecular architecture of the structure can be described by being composed of these chains inter-locked by additional C-H?Br short contacts. An intra-molecular N-H?O=C bridge, as well as weak C-H?O hydrogen bonds, are also present in the structure.

| S-EPMC2968325 | biostudies-literature

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