3-(4-Chloro­phen­yl)-5-phenyl-1,2,4-triazolo[3,4-a]isoquinoline

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

doi:10.1107/S1600536810013668

. 2010 Apr 17;66(Pt 5):o1094. doi: 10.1107/S1600536810013668

3-(4-Chlorophenyl)-5-phenyl-1,2,4-triazolo[3,4-a]isoquinoline

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

PMCID: PMC2979237 PMID: 21579147

Abstract

In the title molecule, C₂₂H₁₄ClN₃, the triazoloisoquinoline ring system is approximately planar, with an r.m.s. deviation of 0.033 (2) Å and a maximum departure from the mean plane of 0.062 (1) Å for the triazole ring C atom, bonded to the benzene ring. The benzene and phenyl rings are twisted by 57.02 (6) and 62.16 (6)°, respectively, to the mean plane of the triazoloisoquinoline ring system. The molecule is stabilized by a weak intramolecular π–π interaction [centroid–centroid distance = 3.7089 (10) Å] between the benzene and phenyl rings. In the crystal structure, weak intermolecular C—H⋯N hydrogen bonds and C—H⋯π interactions link the molecules.

Related literature

For the synthesis and antihelmintic activity of triazolo compounds similar to the title compound, see: Nadkarni et al. (2001 ▶); Hui et al. (1999 ▶). For related structures, see: Khan et al. (2010 ▶); Zou et al. (2004 ▶).

Experimental

Crystal data

C₂₂H₁₄ClN₃
M _r = 355.81
Monoclinic,
a = 7.9841 (3) Å
b = 9.0679 (4) Å
c = 23.9881 (11) Å
β = 93.078 (4)°
V = 1734.20 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 290 K
0.40 × 0.32 × 0.25 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 ▶) T _min = 0.902, T _max = 0.945
19413 measured reflections
3216 independent reflections
2090 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.097
S = 0.97
3216 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.21 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/S1600536810013668/bg2341sup1.cif

e-66-o1094-sup1.cif^{(20.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013668/bg2341Isup2.hkl

e-66-o1094-Isup2.hkl^{(154.6KB, hkl)}

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

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

Cg1, Cg2 and Cg3 are the centroids of the N1–N3/C1/C16, N1/C1/C2/C7–C9 and C2–C7 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯N2ⁱ	0.93	2.59	3.514 (2)	170
C8—H8⋯N3ⁱ	0.93	2.62	3.496 (2)	156
C18—H18⋯Cg1ⁱⁱ	0.93	2.70	3.4524 (17)	138
C21—H21⋯Cg3ⁱⁱⁱ	0.93	2.89	3.7139 (19)	149
C22—H22⋯Cg2ⁱⁱⁱ	0.93	2.90	3.5442 (18)	128

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

Acknowledgments

We thank the FIST program for the data collection at SSCU, IISc, Bangalore. We 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, we focused on the synthesis of the titled compound, which crystal structure is reported.

In the title molecule (I), Fig. 1, the triazoloisoquinoline ring system (N1–N3/C1–C9/C16) is approximately planar, with an r.m.s. deviation of 0.033 (2) Å and a maximum departure from the mean plane of -0.062 (1) Å for the triazole ring C16 atom, bonded to the benzene ring (C17–C22). The benzene (C17–C22) and phenyl (C10–C15) rings are twisted by 57.02 (6) and 62.16 (6) ° with respect to the mean plane of the triazoloisoquinoline ring system. The dihedral angle betwen the benzene (C17–C22) and phenyl (C10–C15) rings is 22.21 (8)° .

The molecule is stabilized by a weak intramolecular π-π interaction [Cg4···Cg5(x, y, z) = 3.7089 (10) Å; Cg4 and Cg5 are the centroids of the rings C10–C15 and C17–C22, respectively]. In the crystal structure, weak intermolecular C—H···N hydrogen bonds and C—H···π interactions (Table 1, Fig. 2) link the molecules to each other.

Experimental

2-(3-Phenylisoquinolin-1-yl)hydrazine (1 mmol) was condensed with, 4-chlorobenzaldehyde (1.1 mmol) under refluxing conditions in isopropanol (10 ml) solvent to give the corresponding hydrazone in high yield. After removal of the 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.