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3-Amino-1-(4-meth-oxy-phen-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile.

ABSTRACT: In the title compound, C(23)H(17)N(3)O, significant deviations from planarity are evidenced. This is quanti-fied in the dihedral angles formed between the central amino-benzene ring and the benzene rings of the meth-oxy-benzene [67.93?(8)°] and 1,2-dihydro-naphthalene [28.27?(8)°] residues. In the crystal the amino-H atoms form hydrogen bonds to the meth-oxy-O atom and to one of the cyano-N atoms to generate a two-dimensional array with a zigzag topology that stacks along the ([Formula: see text][Formula: see text] 1) plane.

SUBMITTER: Asiri AM

PROVIDER: S-EPMC3200821 | biostudies-other | 2011 Sep

REPOSITORIES: biostudies-other

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3-Amino-1-(4-meth-oxy-phen-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile.

Asiri Abdullah M AM Al-Youbi Abdulrahman O AO Faidallah Hassan M HM Ng Seik Weng SW Tiekink Edward R T ER

Acta crystallographica. Section E, Structure reports online 20110827 Pt 9

In the title compound, C(23)H(17)N(3)O, significant deviations from planarity are evidenced. This is quanti-fied in the dihedral angles formed between the central amino-benzene ring and the benzene rings of the meth-oxy-benzene [67.93 (8)°] and 1,2-dihydro-naphthalene [28.27 (8)°] residues. In the crystal the amino-H atoms form hydrogen bonds to the meth-oxy-O atom and to one of the cyano-N atoms to generate a two-dimensional array with a zigzag topology that stacks along the ([Formula: see text ...[more]

PMID: 22059017

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3-Amino-1-(3,4-dimeth-oxy-phen-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile.

Project description:In the title compound, C(24)H(19)N(3)O(2), the partially saturated ring adopts a distorted half-chair conformation with the methyl-ene-C atom closest to the amino-benzene ring lying 0.664?(3)?Å out of the plane defined by the five remaining atoms (r.m.s. deviation = 0.1429?Å. The dihedral angle [32.01?(10)°] between the benzene rings on either side of this ring indicates a significant fold in this part of the mol-ecule. The dimeth-oxy-substituted benzene ring is almost orthogonal to the benzene ring to which it is attached [dihedral angle = 72.03?(9)°]. The mol-ecule has been observed previously as the major component of a 1:19 co-crystal with 2-amino-4-(3,4-dimeth-oxy-phen-yl)-5,6-dihydro-benzo[ha]quinoline-3-carbonitrile [Asiri et al. (2011). Acta Cryst. E67, o2873-o2873]. Supra-molecular chains with base vector [201] are formed in the crystal structure via N-H?O hydrogen bonds between the amino H atoms of one mol-ecule inter-acting with the meth-oxy O atoms of a neighbouring mol-ecule. The chains are linked into a three-dimensional architecture by C-H?? inter-actions.

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A second monoclinic polymorph for 3-amino-1-(4-meth-oxy-phen-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile.

Project description:The title compound, C(23)H(17)N(3)O, has been previously described in a monoclinic P2(1)/c polymorph with Z = 4 [Asiri, Al-Youbi, Faidallah, Ng & Tiekink (2011). Acta Cryst. E67, o2449]. In the new monoclinic P2(1)/n form, with Z = 8, there are two independent mol-ecules, A and B, in the asymmetric unit. In both mol-ecules, the cyclo-hexa-1,3-diene ring has a screw-boat conformation, whereas it is a distorted half-chair in the original polymorph. There is a fold in each mol-ecule, as indicated by the dihedral angle between the benzene rings of the 1,2-dihydro-naphthalene and aniline residues of 33.19?(10)° (mol-ecule A) and 30.6?(10)° (mol-ecule B). The meth-oxy-benzene ring is twisted out of the plane of the aniline residue to which it is connected [dihedral angles = 49.22?(10) and 73.27?(10)°, in A and B respectively]. In the crystal, the two independent mol-ecules self-associate via N-H?N hydrogen bonds, generating a 12-membered {?HNC(3)N}(2) synthon. These are connected into a supra-molecular tape in the (-101) plane by N-H?O(meth-oxy) inter-actions. In the P2(1)/c polymorph, supra-molecular layers are formed by N-H?N and N-H?O inter-actions.

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3-Amino-1-(2H-1,3-benzodioxol-5-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile.

Project description:In the title compound, C(23)H(15)N(3)O(2), significant deviations from planarity are evidenced in the values of the dihedral angles formed between the amino-benzene ring and the benzene rings of the 1,3-benzodioxole [65.38 (12)°] and 1,2-dihydro-naphthalene [26.27 (14)°] residues; the dioxole ring has an envelope conformation with the methyl-ene-C being the flap atom. The amino-H atoms form hydrogen bonds to one of the dioxole-O atoms and to one of the cyano-N atoms to generate a two-dimensional array with a zigzag topology that stacks along the ([Formula: see text] 0 2) plane.

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2-Amino-4-(4-chloro-phen-yl)-5,6-dihydro-benzo[h]quinoline-3-carbonitrile-3-amino-1-(4-chloro-phen-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile (1/4).

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| S-EPMC3379200 | biostudies-literature

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