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

Abdullah M Asiri; Abdulrahman O Al-Youbi; Hassan M Faidallah; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536811033617

. 2011 Aug 27;67(Pt 9):o2449. doi: 10.1107/S1600536811033617

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

Abdullah M Asiri ^a,^b,^‡, Abdulrahman O Al-Youbi ^a, Hassan M Faidallah ^a, Seik Weng Ng ^c, Edward R T Tiekink ^c,^*

PMCID: PMC3200821 PMID: 22059017

Abstract

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 ( Inline graphic 1) plane.

Related literature

For background to the biological activity of related compounds, see: Aly et al. (1991 ▶); Al-Saadi et al. (2005 ▶); Rostom et al. (2011 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶). For a related structure, see: Asiri et al. (2011 ▶).

Experimental

Crystal data

C₂₃H₁₇N₃O
M _r = 351.40
Monoclinic,
a = 9.0212 (4) Å
b = 22.1475 (8) Å
c = 9.3114 (4) Å
β = 110.410 (5)°
V = 1743.60 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.25 × 0.25 × 0.05 mm

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.714, T _max = 1.000
8688 measured reflections
3890 independent reflections
2953 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.116
S = 1.04
3890 reflections
252 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811033617/hg5084sup1.cif

e-67-o2449-sup1.cif^{(21.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033617/hg5084Isup2.hkl

e-67-o2449-Isup2.hkl^{(190.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811033617/hg5084Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯O1ⁱ	0.89 (1)	2.21 (1)	3.0307 (19)	154 (2)
N2—H2⋯N1ⁱⁱ	0.88 (1)	2.33 (1)	3.115 (2)	149 (2)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank King Abdulaziz University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The study of the title compound (I) was motivated by recent reports of the biological activity of related compounds (Aly et al., 1991; Al-Saadi et al., 2005; Rostom et al., 2011) and allied crystal structure investigations (Asiri et al., 2011).

The structure of (I), Fig. 1, is isostructural with the derivative in which the methoxybenzene group in (I) is substituted for a 2H-1,3-benzodioxol-5-yl group (Asiri et al., 2011). With respect to the amino-benzene ring, the benzene rings of the methoxybenzene and 1,2-dihydronaphthalene residues form dihedral angles of 67.93 (8) and 28.27 (8) °, respectively, indicating non-planarity in the molecule. In the 1,2-dihydronaphthalene residue, the cyclohexa-1,3-diene ring has a distorted half-chair conformation as defined by the following parameters (Cremer & Pople, 1975): q₂ = 0.5166 (18) Å, φ₂ = 84.4 (2) °, q₃ = 0.1891 (19) Å, and puckering amplitude Q = 0.5501 (19) Å.

In the crystal structure, supramolecular arrays with zigzag topology and running parallel to the (11 1) plane are formed through N—H···O(methoxy) and N—H···N(cyano) hydrogen bonding, Table 1 and Fig. 2.

Experimental

A mixture of the 4-anisaldehyde (1.36 g,10 mmol), 1-tetralone (1.46 g, 10 mmol), ethyl cyanoacetate (1.1 g, 10 mmol) and ammonium acetate (6.2 g, 80 mmol) in absolute ethanol (50 ml) was refluxed for 6 h. The reaction mixture was allowed to cool and the precipitate that formed was filtered, washed with water, dried and recrystallized from DMF; M.pt.: 487–488 K.