(IUCr) 2,6-Bis(1-isopropyl-5-phenyl-1H-pyrazol-3-yl)pyridine

Volume 64
Part 1
Page o226
January 2008

Received 20 November 2007
Accepted 3 December 2007
Online 6 December 2007

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.047
wR = 0.123
Data-to-parameter ratio = 14.1
Details

2,6-Bis(1-isopropyl-5-phenyl-1H-pyrazol-3-yl)pyridine

Ping Liu,^a Yong-Bo Zhou,^b ^* Min-Guo Li ^c and Cai-Xia An ^a

^aSchool of Chemistry and Chemical Engineering, Henan Institute of Science and Technology, Xinxiang, Henan 453003, People's Republic of China,^bDepartment of Chemistry, Zhejiang University, Xixi Campus, Hangzhou 310028, People's Republic of China, and ^cDepartment of Agriculture, Guangshan County, Henan 465400, People's Republic of China
Correspondence e-mail: zybdjy@163.com

In the title compound, C₂₉H₂₉N₅, the central pyridine ring and the two pyrazole rings are approximately coplanar, the dihedral angles between the pyridine and pyrazole rings being 3.94 (12) and 14.84 (12)°. The pyrazole and phenyl rings on each side of the molecule are twisted with dihedral angles of 46.72 (8) and 73.39 (8)°. One phenyl ring interacts with a pyrazole ring of a neighbouring molecule via a weak intermolecular C-H [pi] interaction, which stabilizes the molecular packing.

Related literature

For general background, see: Dias & Gamage (2007); Zhou & Chen (2007).

Experimental

Crystal data

C₂₉H₂₉N₅
M_r = 447.57
Triclinic, $[P \overline 1]$
a = 9.973 (3) Å
b = 10.172 (3) Å
c = 14.014 (4) Å
= 110.940 (4)°
= 106.494 (4)°
= 94.583 (4)°
V = 1246.8 (6) Å³
Z = 2
Mo K radiation
= 0.07 mm^-1
T = 298 (2) K
0.53 × 0.43 × 0.39 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) T_min = 0.963, T_max = 0.972
6572 measured reflections
4332 independent reflections
2417 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.123
S = 1.05
4332 reflections
307 parameters
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C20-H20Cg1ⁱ	0.93	2.86	3.710 (3)	153
Symmetry code: (i) -x+1, -y, -z. Cg1 is the centroid of the C6-C8/N2/N3 pyrazole ring.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2264 ).

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dias, H. V. R. & Gamage, C. S. P. (2007). Angew. Chem. Int. Ed. 46, 2192-2194.
Sheldrick, G. M. (2001). SHELXTL. Version 6.10. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2002). SADABS. Version 2.03. University of Göttingen, Germany.
Westrip, S. P. (2008). publCIF. In preparation.
Zhou, Y. B. & Chen, W. Z. (2007). Dalton Trans. pp. 5123-5125.