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Volume 69 
Part 8 
Page o1316  
August 2013  

Received 23 June 2013
Accepted 18 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.073
wR = 0.241
Data-to-parameter ratio = 12.5
Details
Open access

N,N-Diethyl-4-[1-phenyl-3-(pyridin-2-yl)-4,5-dihydro-1H-pyrazol-5-yl]aniline

aDepartment of Chemistry, Anhui University, Hefei 230039, People's Republic of China, and bKey Laboratory of Functional Inorganic Materials Chemistry, Hefei 230039, People's Republic of China
Correspondence e-mail: yptian@ahu.edu.cn

In the title molecule, C24H26N4, the pyrazoline ring assumes an envelope conformation with the aniline-bearing C atom at the flap position. The benzene ring and the pyridine ring form with the pyrazoline ring dihedral angles of 4.53 (1) and 6.26 (1)°, respectively. In turn, the aniline group is nearly perpendicular to the pyrazoline ring [dihedral angle = 79.96 (1)°]. The ethyl groups of the diethylamine substituent are disordered over two sets of sites, with an occupancy ratio of 0.624 (8):0.376 (8).

Related literature

For background to the design and synthesis of the title compound and for related structures, see: Chen et al. (2008[Chen, Y., Li, D.-C., Zhu, Y. & Wang, D.-Q. (2008). Acta Cryst. E64, o1629.]); Dong et al. (2010[Dong, B.-L., Wang, M.-L. & Li, Y.-H. (2010). Acta Cryst. E66, o2786.]); Guo et al. (2010[Guo, H.-M., Huang, B.-Y., Qin, X., Zou, H.-Z. & Jian, F.-F. (2010). Acta Cryst. E66, o1587.]); Liu et al. (2010[Liu, W.-Y., Xie, Y.-S., Wang, B.-S. & Zhao, B.-X. (2010). Acta Cryst. E66, m1275.]).

[Scheme 1]

Experimental

Crystal data
  • C24H26N4

  • Mr = 370.49

  • Monoclinic, P 21 /c

  • a = 14.902 (5) Å

  • b = 11.314 (5) Å

  • c = 12.479 (5) Å

  • [beta] = 94.644 (5)°

  • V = 2097.1 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 296 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.979, Tmax = 0.986

  • 14365 measured reflections

  • 3678 independent reflections

  • 2511 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.073

  • wR(F2) = 0.241

  • S = 1.06

  • 3678 reflections

  • 294 parameters

  • 507 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.52 e Å-3

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2584 ).


Acknowledgements

This work was supported by grants from the National Natural Science Foundation of China (grant No. 21271004) and the Natural Science Foundation of Anhui Province (grant No. 1208085MB22).

References

Bruker (2000). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, Y., Li, D.-C., Zhu, Y. & Wang, D.-Q. (2008). Acta Cryst. E64, o1629.  [CrossRef] [IUCr Journals]
Dong, B.-L., Wang, M.-L. & Li, Y.-H. (2010). Acta Cryst. E66, o2786.  [CrossRef] [IUCr Journals]
Guo, H.-M., Huang, B.-Y., Qin, X., Zou, H.-Z. & Jian, F.-F. (2010). Acta Cryst. E66, o1587.  [CrossRef] [IUCr Journals]
Liu, W.-Y., Xie, Y.-S., Wang, B.-S. & Zhao, B.-X. (2010). Acta Cryst. E66, m1275.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1316  [ doi:10.1107/S1600536813019879 ]

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