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

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

doi:10.1107/S160053681001278X

. 2010 Apr 10;66(Pt 5):o1056–o1057. doi: 10.1107/S160053681001278X

5-(4-Chlorophenyl)-3-(2,4-dimethylthiazol-5-yl)-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: PMC2979146 PMID: 21579114

Abstract

In the title molecule, C₂₁H₁₅ClN₄S, the triazoloisoquinoline ring system is approximately planar, with an r.m.s. deviation of 0.054 (2) Å and a maximum deviation of 0.098 (2) Å from the mean plane for the triazole ring C atom that is bonded to the thiazole ring. The thiazole and benzene rings are twisted by 66.36 (7) and 56.32 (7)°, respectively, with respect to the mean plane of the triazoloisoquinoline ring system. In the crystal structure, molecules are linked by intermolecular C—H⋯N interactions along the a axis. The molecular conformation is stabilized by a weak intramolecular π–π interaction involving the thiazole and benzene rings, with a centroid–centroid distance of 3.6546 (11) Å. In addition, two other intermolecular π–π stacking interactions are observed, between the triazole and benzene rings and between the dihydropyridine and benzene rings [centroid–centroid distances = 3.6489 (11) and 3.5967 (10) Å, respectively].

Related literature

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

Experimental

Crystal data

C₂₁H₁₅ClN₄S
M _r = 390.89
Triclinic,
a = 7.8286 (5) Å
b = 8.1754 (6) Å
c = 15.1264 (9) Å
α = 93.514 (5)°
β = 94.805 (5)°
γ = 105.963 (6)°
V = 923.92 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 290 K
0.40 × 0.25 × 0.24 mm

Data collection

Oxford Xcalibur diffractometer with an Eos (Nova) CCD detector
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 ▶) T _min = 0.851, T _max = 0.924
19579 measured reflections
3439 independent reflections
2518 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.111
S = 1.09
3439 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.20 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/S160053681001278X/fj2293sup1.cif

e-66-o1056-sup1.cif^{(21.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001278X/fj2293Isup2.hkl

e-66-o1056-Isup2.hkl^{(165.2KB, 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
C6—H6⋯N2ⁱ	0.93	2.62	3.495 (2)	158
C8—H8⋯N3ⁱ	0.93	2.51	3.383 (2)	156

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the FIST program for data collection on the single-crystal diffractometer 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

Drugs including alprazolam (tranquilizer), estazolam (hypnotic, sedative, tranquilizer), rilmazafon (hypnotic, anxiolytic, used in the case of neurotic insomnia), benatradin (diuretic), trapidil (hypotensive), trazodon (antidepressant, anxiolytic), etoperidone (antidepressant), nefazodone (antidepressant, 5-HT2 A-antagonist), anastazole (antineoplastic, non-steroidal aromatase inhibitor), letrozole (antineoplastic, aromatase inhibitor), ribavirin (antiviral), fluconazole, itraconazole, terconazole (antifungal) possess 1,2,4-Triazole as the structural element. Besides, it follows from the literature data that 1,2,4-triazoles and their fused systems show antibacterial, antifungal and antiflammatory properties. As part of our search for new isoquinoline analogues, we focused on synthesis of titled compounds and the crystal structure is reported.

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 0.054 (2) Å and a maximum deviation of 0.098 (2) Å from the mean plane for the triazole ring C16 atom which is bonded to the thiazole ring (S1/N4/C17/C18/C20). The thiazole (S1/N4/C17/C18/C20) and benzene (C10—C15) rings are twisted by 66.36 (7) and 56.32 (7)°, respectively, with respect to the mean plane of the triazoloisoquinoline ring system. The thiazole ring forms a dihedral angle of 23.34 (9)° with benzene ring.

In the crystal structure of (I), molecules are linked by intermolecular C—H···N interactions along the [100] direction (Table 1, Fig. 2). Furthermore, π-π interactions [Cg1···Cg5(x, y, z) = 3.6546 (11) Å and Cg2···Cg4(2-x, 2-y, 1-z) = 3.6489 (11) Å. Where Cg1, Cg2, Cg4 and Cg5 are the centroids of the S1/N4/C17/C18/C20, N1–N3/C1/C16, C2–C7 and C10–C15 rings, respectively] are observed.

Experimental

2-(3-(4-Chlorophenylisoquinolin-1-yl)hydrazine (1 mmol) was condensed with 2,4-dimethylthiazole-5-carbaldehyde (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.