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

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

doi:10.1107/S1600536810012924

. 2010 Apr 14;66(Pt 5):o1061. doi: 10.1107/S1600536810012924

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

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

PMCID: PMC2979100 PMID: 21579118

Abstract

In the title molecule, C₂₀H₁₂ClN₃O, the triazoloisoquinoline ring system is nearly planar, with an r.m.s. deviation of 0.018 (3) Å and a maximum deviation of 0.034 (3) Å from the mean plane for the triazole ring C atom which is bonded to the benzene ring. The furan and benzene rings are twisted by 59.71 (14) and 66.95 (10)°, respectively, with respect to the mean plane of the triazoloisoquinoline ring system. The molecular conformation is stabilized by an intramolecular π–π interaction [centroid-to-centroid distance = 3.5262 (18) Å]. The crystal packing is stabilized by weak C—H⋯π interactions and weak π–π interactions [centroid-to-centroid distance = 3.9431 (17) Å].

Related literature

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

Experimental

Crystal data

C₂₀H₁₂ClN₃O
M _r = 345.78
Orthorhombic,
a = 9.0281 (9) Å
b = 12.6034 (11) Å
c = 14.6444 (15) Å
V = 1666.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 290 K
0.32 × 0.24 × 0.15 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.933, T _max = 0.964
9280 measured reflections
3029 independent reflections
1831 reflections with I > 2σ(I)
R _int = 0.071

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.082
S = 0.85
3029 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.14 e Å⁻³
Absolute structure: Flack (1983 ▶), with 1245 Freidel pairs
Flack parameter: 0.00 (8)

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810012924/pv2272sup1.cif

e-66-o1061-sup1.cif^{(22.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012924/pv2272Isup2.hkl

e-66-o1061-Isup2.hkl^{(148.7KB, hkl)}

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

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

Cg2 is the centroid of the N1–N3/C1/C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯Cg2ⁱ	0.93	2.95	3.273 (4)	102

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the FIST programme for the data collection on the Oxford single-crystal diffractometer at the SSCU, IISc, Bangalore. We 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 the title compound and its crystal structure is reported in this article.

In the title molecule (I), Fig. 1, the triazoloisoquinoline ring system (N1–N3/C1–C9/C16) is nearly planar, with an r.m.s. deviation of 0.018 (3) Å and a maximum deviation of 0.034 (3) Å from the mean plane for the triazole ring C16 atom which is bonded to the benzene ring. The furan (O1/C17–C20) and benzene (C10–C15) rings are twisted by 59.71 (14) and 66.95 (10)°, respectively, with respect to the mean plane of the triazoloisoquinoline ring system. The furan (O1/C17–C20) and benzene (C10–C15) rings make a dihedral angle of 21.76 (16)° with each other. The molecular conformation is stabilized by an intramolecular π–π interaction [Cg1···Cg5(x, y, z) = 3.5262 (18) Å; Cg1 and Cg5 are the centroids of the O1/C17–C20 and C10–C15 rings, respectively]. In the crystal structure, there is no classical hydrogen bonds. The crystal packing is stabilized by weak C—H···π interactions (Table 1) and weak π–π interactions [Cg1···Cg2(1/2 + x, 3/2 - y, 1 - z) = 3.9431 (17) Å; Cg2 is the centroid of the N1–N3/C1/C16 ring]. Fig. 2 shows the packing diagram of (I) viewing down the a axis.

Experimental

2-(3-(4-Chlorophenylisoquinolin-1-yl)hydrazine (1 mmol) was condensed with furan-2-carbaldehyde (1.1 mmol) under refluxing conditions in 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.