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

ABSTRACT: In the title compound, C(20)H(13)N(3)S, the partially saturated ring adopts a twisted half-boat conformation with the methyl-ene C atom closest to the amino-benzene ring lying 0.690 (6) Å out of the plane defined by the five remaining atoms. The dihydro-phenanthrene residue has a folded conformation [dihedral angle between the outer benzene rings = 26.27 (18)°]. The thio-phen-2-yl ring forms a dihedral angle of 63.76 (19)° with the benzene ring to which it is attached. In the crystal, inversion dimers linked by pairs of N-H⋯N hydrogen bonds generate R(2) (2)(12) loops. The dimers are linked into layers in the bc plane by weak C-H⋯π inter-actions. The thio-phen-2-yl ring is disordered over two essentially coplanar but opposite orientations in a 0.918 (4):0.082 (4) ratio.

SUBMITTER: Al-Youbi AO

PROVIDER: S-EPMC3343991 | biostudies-literature |

REPOSITORIES: biostudies-literature

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

Project description:In the title compound, C(22)H(14)BrN(3), the fused-ring system is buckled owing to the ethyl-ene linkage in the central ring; the two flanking aromatic rings are twisted by 25.9?(1) ° with respect to each other. The phenyl ring is twisted by 77.0?(1)° relative to the amino- and cyano-bearing aromatic ring. In the crystal, adjacent mol-ecules are linked by two N-H?N hydrogen bonds, generating a zigzag chain along [101].

| S-EPMC3201339 | biostudies-literature

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.

| S-EPMC3344065 | biostudies-literature

3-Amino-1-methyl-9,10-dihydro-phenanthrene-2,4-dicarbonitrile.

Project description:The asymmetric unit of the title compound, C(17)H(13)N(3), contains two independent mol-ecules, which are non-planar as they are buckled owing to the ethyl-ene portion. The dihedral angle between the benzene rings is 26.4?(1)° in one mol-ecule and 32.9?(1)° in the other. In the crystal, the mol-ecules are disposed about a false inversion center, and are linked by two N-H?N hydrogen bonds, generating a dimer. The dimers are linked by further N-H?N hydrogen bonds, resulting in a chain that runs along the longest axis of the ortho-rhom-bic unit cell.

| S-EPMC3201274 | biostudies-literature

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

Project description: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.

| S-EPMC3200821 | biostudies-other

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.

| S-EPMC3200934 | biostudies-literature

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.

| S-EPMC3344100 | biostudies-literature

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).

Project description:The asymmetric unit of the 1:4 title co-crystal of 2-amino-4-(4-chloro-phen-yl)-5,6-dihydro-benzo[h]quinoline-3-carbonitrile and 3-amino-1-(4-chloro-phen-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile, 0.2C(20)H(14)ClN(3)·0.8C(22)H(14)ClN(3), has the atoms of the fused-ring system and those of the amino, cyano and chloro-phenyl substitutents overlapped. The fused-ring system is buckled owing to the ethyl-ene linkage in the central ring. There are two independent overlapped mol-ecules in the asymmetric unit. In one independent mol-ecule, the two flanking aromatic rings are twisted by 24.4?(1)° and the ring of the chloro-phenyl substituent is twisted by 87.3?(1)° relative to the amino- and cyano-bearing aromatic ring. In the second mol-ecule, the respective dihedral angles are 26.1?(1) and 57.8?(1)°. The two independent mol-ecules are linked by N-H?N hydrogen bonds into dimers.

| S-EPMC3247609 | biostudies-literature

2-Amino-4-(3,4-dimeth-oxy-phen-yl)-5,6-dihydro-benzo[h]quinoline-3-carbo-nitrile-3-amino-1-(3,4-dimeth-oxy-phen-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile (1/19).

Project description:The asymmetric unit of the 1:19 title co-crystal of 2-amino-4-(3,4-dimeth-oxy-phen-yl)-5,6-dihydro-benzo[h]quinoline-3-carbo-nitrile and 3-amino-1-(3,4-dimeth-oxy-phen-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile, 0.05C(22)H(19)N(3)O(2)·0.95C(24)H(19)N(3)O(2), has the atoms of the fused-ring system and those of the amino, cyano and dimeth-oxy-phenyl substitutents overlapped. The fused-ring system is buckled owing to the ethyl-ene linkage in the central ring with the two flanking aromatic rings being twisted by 31.9?(1)°. The ring of the dimeth-oxy-phenyl substituent is twisted by 72.4?(1)° relative to the amino- and cyano-bearing aromatic ring. In the crystal, mol-ecules are linked by duplex amine N-H?O(meth-oxy) hydrogen bonds in a cyclic association [graph-set R(2) (2)(7)], generating a helical chain structure extending along [201].

| S-EPMC3247608 | biostudies-literature

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

Project description:The asymmetric unit of the 5:3 title co-crystal of 2-amino-4-phenyl-5,6-dihydro-benzo[h]quinoline-3-carbonitrile and 3-amino-1-phenyl-9,10-dihydro-phenanthrene-2,4-dicarbonitrile, 0.625C(20)H(15)N(3).0.375C(22)H(15)N(3), has the atoms of the fused-ring system and those of the amino, cyano and phenyl substitutents overlapped. The fused-ring system is buckled owing to the ethyl-ene linkage in the central ring, the two flanking aromatic rings being twisted by 20.1?(1)°. This ethyl-ene portion is disordered over two positions in a 1:1 ratio. The phenyl ring is twisted by 69.5?(1)° relative to the amino- and cyano-bearing aromatic ring. In the crystal, two mol-ecules are linked by an N-H?N hydrogen bond, generating a a helical chain along [010].

| S-EPMC3247607 | biostudies-literature

3-Amino-5-(piperidin-1-yl)thio-phene-2,4-dicarbonitrile.

Project description:In the title compound, C(11)H(12)N(4)S, the thio-phene ring is roughly planar, with a maximum deviation of 0.012?(1)?Å for the S atom, and makes a dihedral angle of 7.89?(8)° with the mean plane of the piperidine ring, which is in a chair conformation. The crystal packing is stabilized by pairs of centrosymmetric inter-molecular N-H?N hydrogen bonds, which results in the formation of a step-wise chain parallel to [10[Formula: see text]].

| S-EPMC3254482 | biostudies-literature

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