1-[3-(4-Chloro­phen­yl)isoquinolin-1-yl]-3,5-diphenyl-1H-pyrazole

Khan, F.N.; Manivel, P.; Krishnakumar, V.; Hathwar, V.R.; Ng, S.W.

doi:10.1107/S1600536809055718

Volume 66
Part 2
Page o369
February 2010

Received 28 December 2009
Accepted 30 December 2009
Online 16 January 2010

Key indicators
Single-crystal X-ray study
T = 290 K
Mean (C-C) = 0.003 Å
R = 0.050
wR = 0.126
Data-to-parameter ratio = 14.3
Details

1-[3-(4-Chlorophenyl)isoquinolin-1-yl]-3,5-diphenyl-1H-pyrazole

F. Nawaz Khan,^a P. Manivel,^b V. Krishnakumar,^b Venkatesha R. Hathwar ^c and Seik Weng Ng ^d ^*

^aChemistry Division, School of Science and Humanities, VIT University, Vellore 632014, Tamil Nadu, India,^bChemistry Division, School of Advanced Sciences, VIT University, Vellore 632014, Tamil Nadu, India,^cSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560012, Karnataka, India, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

The title compound, C₃₀H₂₀ClN₃, is composed of a diaryl-substituted pyrazole ring connected to an aryl-substituted isoquinoline ring system with a dihedral angle of 65.1 (1)° between the pyrazole ring and the isoquinoline ring system. The 3-phenyl and 4-phenyl substitutents are twisted by 8.1 (1) and 43.0 (1)°, respectively, with respect to the pyrazole ring. The chlorophenyl ring and the isoquinoline ring system are twisted by 21.2 (1)° with respect to each other.

Related literature

For medicinal applications of hydrazine derivatives, see: Broadhurst et al. (2001).

Experimental

Crystal data

C₃₀H₂₀ClN₃
M_r = 457.94
Monoclinic, P 2₁ /c
a = 23.7864 (15) Å
b = 11.7101 (8) Å
c = 8.3602 (5) Å
= 96.738 (1)°
V = 2312.6 (3) Å³
Z = 4
Mo K radiation
= 0.19 mm^-1
T = 290 K
0.20 × 0.16 × 0.04 mm

Data collection

Bruker SMART area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.963, T_max = 0.993
17230 measured reflections
4392 independent reflections
2890 reflections with I > 2(I)
R_int = 0.039

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.126
S = 1.02
4392 reflections
307 parameters
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.19 e Å^-3

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5160 ).

Acknowledgements

We thank the Department of Science and Technology, India, for use of the diffraction facility at IISc under the IRHPA-DST program. FNK thanks the DST for Fast Track Proposal funding. We thank VIT University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Broadhurst, M. J., Johnson, W. H. & Walter, D. S. (2001). US Patent No. 6235787.
Bruker (2004). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). publCIF. In preparation.

organic compounds