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N-Acetyl-N-[2,4-dicyano-1-(4-meth-oxy-phen-yl)-9,10-dihydro-phenanthren-3-yl]acetamide.

ABSTRACT: In the title compound, C(27)H(21)N(3)O(3), the cyclo-hexa-1,3-diene ring has a screw-boat conformation, and the fused ring system is folded, the dihedral angle between the outer benzene rings being 27.61?(6)°. The N-acetyl-acetamide residue (r.m.s. deviation = 0.0935?Å) has an anti conformation and is essentially perpendicular to the benzene ring to which it is connected [dihedral angle = 89.14?(6)°]; the meth-oxy-benzene group is also twisted out of this ring [dihedral angle = 59.47?(7)°]. The three-dimensional architecture is consolidated by C-H?O and C-H?? inter-actions.

SUBMITTER: Asiri AM

PROVIDER: S-EPMC3344116 | biostudies-literature | 2012 Apr

REPOSITORIES: biostudies-literature

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N-Acetyl-N-[2,4-dicyano-1-(4-meth-oxy-phen-yl)-9,10-dihydro-phenanthren-3-yl]acetamide.

Asiri Abdullah M AM Faidallah Hassan M HM Al-Thabaiti Shaeel A SA Ng Seik Weng SW Tiekink Edward R T ER

Acta crystallographica. Section E, Structure reports online 20120324 Pt 4

In the title compound, C(27)H(21)N(3)O(3), the cyclo-hexa-1,3-diene ring has a screw-boat conformation, and the fused ring system is folded, the dihedral angle between the outer benzene rings being 27.61 (6)°. The N-acetyl-acetamide residue (r.m.s. deviation = 0.0935 Å) has an anti conformation and is essentially perpendicular to the benzene ring to which it is connected [dihedral angle = 89.14 (6)°]; the meth-oxy-benzene group is also twisted out of this ring [dihedral angle = 59.47 (7)°]. The ...[more]

PMID: 22606119

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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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