4a-Methyl-2,3,4,4a-tetra­hydro-1H-carbazole-6-sulfonamide

In the title mol­ecule, C13H16N2O2S, the nine non-H atoms comprising the indole residue are approximately coplanar (r.m.s. deviation = 0.031 Å). The partially saturated ring adopts a chair conformation. One amine H forms an inter­molecular N—H⋯O hydrogen bond to a sulfonamide O atom, while the other amine H form is connected to the indole N atom of an adjacent mol­ecule via an N—H⋯N hydrogen bond, resulting in a three-dimensional architecture

2-Amino-4-phenyl-5,6-dihydro­benzo[h]quinoline-3-carbonitrile–3-amino-1-phenyl-9,10-dihydro­phenanthrene-2,4-dicarbonitrile (5/3)

The asymmetric unit of the 5:3 title co-crystal of 2-amino-4-phenyl-5,6-dihydro­benzo[h]quinoline-3-carbonitrile and 3-amino-1-phenyl-9,10-dihydro­phenanthrene-2,4-dicarbonitrile, 0.625C20H15N3.0.375C22H15N3, 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 ethyl­ene linkage in the central ring, the two flanking aromatic rings being twisted by 20.1 (1)°. This ethyl­ene 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 mol­ecules are linked by an N—H⋯N hydrogen bond, generating a a helical chain along [010]

3-Amino-1-(4-bromo­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile

In the title compound, C22H14BrN3, the fused-ring system is buckled owing to the ethyl­ene 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 mol­ecules are linked by two N–H⋯N hydrogen bonds, generating a zigzag chain along [101]

3,5-Dimethyl-1-phenyl-1H-pyrazole-4-carbaldehyde

In the title mol­ecule, C12H12N2O, the five- and six-membered rings form a dihedral angle of 68.41 (16)°. The aldehyde group is nearly coplanar with the pyrazole ring [C—C—C—O torsion angle = −0.4 (5)°]. The three-dimensional architecture is sustained by weak C—H⋯O and C—H⋯π inter­actions

(2E)-2-[(2H-1,3-Benzodioxol-5-yl)methyl­idene]-2,3-dihydro-1H-inden-1-one

In the title compound, C17H12O3, each of the five-membered rings in the inden-1-one and 1,3-benzodioxole residues is almost planar (r.m.s. deviations = 0.041 and 0.033 Å, respectively). A small twist about the single bond linking the two residues is evident [the C—C—C—C torsion angle = 8.7 (4)°]. Supra­molecular zigzag layers propagating in the ac plane are formed in the crystal via C—H⋯O inter­actions. The layers are linked via π–π inter­actions between the five- and six-membered rings of 1,3-benzodioxole residues [centroid–centroid distance = 3.4977 (14) Å]

3-Amino-1-(thio­phen-2-yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile

In the title compound, C20H13N3S, the partially saturated ring adopts a twisted half-boat conformation with the methyl­ene C atom closest to the amino­benzene ring lying 0.690 (6) Å out of the plane defined by the five remaining atoms. The dihydro­phenanthrene residue has a folded conformation [dihedral angle between the outer benzene rings = 26.27 (18)°]. The thio­phen-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 inter­actions. The thio­phen-2-yl ring is disordered over two essentially coplanar but opposite orientations in a 0.918 (4):0.082 (4) ratio

2-[(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)methyl­idene]indan-1,3-dione

In the title compound, C21H16N2O2, the five-membered heterocyclic ring makes a dihedral angle of 47.06 (6)° with the attached benzene ring, whereas the indan-1,3-dione ring system and the benzene ring are oriented at a dihedral angle of 21.92 (7)°. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R 2 2(22) loops. Aromatic π–π stacking inter­actions [centroid–centroid distances = 3.8325 (12)–3.8600 (12) Å] also occur

3-Amino-1-(3,4-dimeth­oxy­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile

In the title compound, C24H19N3O2, the partially saturated ring adopts a distorted half-chair conformation with the methyl­ene-C atom closest to the amino­benzene 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 mol­ecule. The dimeth­oxy-substituted benzene ring is almost orthogonal to the benzene ring to which it is attached [dihedral angle = 72.03 (9)°]. The mol­ecule has been observed previously as the major component of a 1:19 co-crystal with 2-amino-4-(3,4-dimeth­oxy­phen­yl)-5,6-dihydro­benzo[ha]quinoline-3-carbonitrile [Asiri et al. (2011). Acta Cryst. E67, o2873–o2873]. Supra­molecular chains with base vector [201] are formed in the crystal structure via N—H⋯O hydrogen bonds between the amino H atoms of one mol­ecule inter­acting with the meth­oxy O atoms of a neighbouring mol­ecule. The chains are linked into a three-dimensional architecture by C—H⋯π inter­actions

A second monoclinic polymorph for 3-amino-1-(4-meth­oxy­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile

The title compound, C23H17N3O, has been previously described in a monoclinic P21/c polymorph with Z = 4 [Asiri, Al-Youbi, Faidallah, Ng & Tiekink (2011). Acta Cryst. E67, o2449]. In the new monoclinic P21/n form, with Z = 8, there are two independent mol­ecules, A and B, in the asymmetric unit. In both mol­ecules, the cyclo­hexa-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 mol­ecule, as indicated by the dihedral angle between the benzene rings of the 1,2-dihydro­naphthalene and aniline residues of 33.19 (10)° (mol­ecule A) and 30.6 (10)° (mol­ecule B). The meth­oxy­benzene 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 mol­ecules self-associate via N—H⋯N hydrogen bonds, generating a 12-membered {⋯HNC3N}2 synthon. These are connected into a supra­molecular tape in the (-101) plane by N—H⋯O(meth­oxy) inter­actions. In the P21/c polymorph, supra­molecular layers are formed by N—H⋯N and N—H⋯O inter­actions

3-Amino-1-(4-meth­oxy­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile

In the title compound, C23H17N3O, significant deviations from planarity are evidenced. This is quanti­fied in the dihedral angles formed between the central amino-benzene ring and the benzene rings of the meth­oxy­benzene [67.93 (8)°] and 1,2-dihydro­naphthalene [28.27 (8)°] residues. In the crystal the amino-H atoms form hydrogen bonds to the meth­oxy-O atom and to one of the cyano-N atoms to generate a two-dimensional array with a zigzag topology that stacks along the ( 1) plane