4-(5-Phenyl-1,2,4-triazolo[3,4-a]isoquinolin-3-yl)benzonitrile

F Nawaz Khan; P Manivel; K Prabakaran; Venkatesha R Hathwar; Mehmet Akkurt

doi:10.1107/S1600536810013012

. 2010 Apr 14;66(Pt 5):o1081. doi: 10.1107/S1600536810013012

4-(5-Phenyl-1,2,4-triazolo[3,4-a]isoquinolin-3-yl)benzonitrile

F Nawaz Khan ^a, P Manivel ^a, K Prabakaran ^a, Venkatesha R Hathwar ^b, Mehmet Akkurt ^c,^*

PMCID: PMC2979274 PMID: 21579135

Abstract

In the title molecule, C₂₃H₁₄N₄, the triazoloisoquinoline ring system is nearly planar, with an r.m.s. deviation of 0.038 (2) Å and a maximum deviation of −0.030 (2) Å from the mean plane of the triazole ring C atom which is bonded to the benzene ring. The benzene and phenyl rings are twisted by 57.65 (8) and 53.60 (9)°, respectively, with respect to the mean plane of the triazoloisoquinoline ring system. In the crystal structure, molecules are linked by weak aromatic π–π interactions [centroid–centroid distance = 3.8074 (12) Å]. In addition, the crystal structure exhibits a nonclassical intermolecular C—H⋯N hydrogen bond.

Related literature

For a related crystal structure, see: Khan et al. (2010 ▶).

Experimental

Crystal data

C₂₃H₁₄N₄
M _r = 346.38
Orthorhombic,
a = 7.1614 (3) Å
b = 18.0957 (7) Å
c = 26.4021 (9) Å
V = 3421.5 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 290 K
0.25 × 0.21 × 0.17 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 ▶) T _min = 0.959, T _max = 0.986
14977 measured reflections
3164 independent reflections
1490 reflections with I > 2σ(I)
R _int = 0.070

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.100
S = 0.81
3164 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810013012/rk2199sup1.cif

e-66-o1081-sup1.cif^{(20.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013012/rk2199Isup2.hkl

e-66-o1081-Isup2.hkl^{(152.2KB, hkl)}

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
C11—H11⋯N3ⁱ	0.93	2.50	3.418 (3)	170

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the FIST program for data collection on the Oxford single-crystal diffractometer at SSCU, IISc, Bangalore. The authors also thank Professor T. N. Guru Row, IISc, Bangalore, for his help with the data collection. FNK thanks the DST for Fast Track Proposal funding.

supplementary crystallographic information

Comment

As part of our search for new isoquinoline analogues (Khan et al., 2010), we focused on synthesis of titled compounds and the crystal structure is reported.

In the title molecule, Fig. 1, the triazoloisoquinoline ring system (N1-N3/C1-C9/C16) is nearly planar, with an r.m.s. deviation of 0.038 (2)Å and a maximum deviation of -0.030 (2)Å from the mean plane for the triazole ring C16 atom which is bonded to the benzene ring (C17-C22). The benzene (C17-C22) and phenyl (C10-C15) rings are twisted by 57.65 (8)° and 53.60 (9)°, respectively, with respect to the mean plane of the triazoloisoquinoline ring system. The benzene (C17-C22) and phenyl (C10-C15) rings make a dihedral angle of 29.10 (11)° with each other.

Molecular conformation is stabilized by a weak π–π interaction [Cg4···Cg5 = 3.8229 (14)Å, where are Cg4 and Cg5 are centroids of the C10-C15 and C17-C22 rings, respectively]. In the crystal structure, the molecules are linked by weak aromatic π–π interactions [Cg1···Cg1ⁱⁱ = 3.8074 (12)Å, symmetry code: (ii) x-1/2, 1/2-y, -z. Cg1 is the centroid of the N1-N3/C1/C16 ring]. In addition, the crystal structure exhibits an intermolecular non-classical C–H···N hydrogen bond (Table 1, Fig. 2).

Experimental

2-(3-Phenylisoquinolin-1-yl)hydrazine (1 mmol) was condensed with 4-formylbenzonitrile (1.1 mmol) under refluxing conditions isopropanol (10 ml) solvent to give the corresponding hydrazone in high yield. After removal of solvent the compound was then oxidatively cyclized in nitrobenzene (10 ml) at 473 K. The product was recrystallized from dichlomethane to give block-shaped crystals.