2-[(5-Amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)(4-chloro­phen­yl)meth­yl]malononitrile

Zhang, X.-Y.; Li, X.-Y.; Wang, X.; Li, D.-F.; Fan, X.-S.

doi:10.1107/S1600536808011562

Volume 64
Part 5
Page o908
May 2008

Received 17 April 2008
Accepted 22 April 2008
Online 26 April 2008

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.041
wR = 0.119
Data-to-parameter ratio = 19.7
Details

2-[(5-Amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)(4-chlorophenyl)methyl]malononitrile

Xin-Ying Zhang,^a ^* Xiao-Yan Li,^a Xia Wang,^a Dong-Fang Li ^a and Xue-Sen Fan ^a ^*

^aSchool of Chemical and Environmental Sciences, Henan Key Laboratory for Environmental Pollution Control, Henan Normal University, Xinxiang, Henan 453007, People's Republic of China
Correspondence e-mail: xyzh518@sohu.com, xuesen.fan@sohu.com

In the crystal structure of the title compound, C₂₀H₁₆ClN₅, the dihedral angle between the pyrazole ring and the phenyl ring is 54.7 (1)° and that between the pyrazole ring and the chloro-substituted phenyl ring is 72.4 (1)°. The methyl H atoms are disordered over two positions with site occupancy factors of ca 0.7 and 0.3. One amino H is disordered equally over two positions. In the crystal structure, the molecules are linked via intermolecular N-HN hydrogen bonding.

Experimental

Crystal data

C₂₀H₁₆ClN₅
M_r = 361.83
Orthorhombic, P b c a
a = 10.4700 (11) Å
b = 14.0482 (15) Å
c = 25.409 (3) Å
V = 3737.3 (7) Å³
Z = 8
Mo K radiation
= 0.22 mm^-1
T = 294 (2) K
0.49 × 0.48 × 0.45 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997) T_min = 0.901, T_max = 0.908
32456 measured reflections
4661 independent reflections
3055 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.118
S = 1.03
4661 reflections
237 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H1N3N4ⁱ	0.86	2.41	3.159 (2)	146
N3-H2N3N2ⁱⁱ	0.86	2.53	3.325 (2)	155
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2101 ).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 20772025), the Program for Science & Technology Innovation Talents in Universities of Henan Province (No. 2008HASTIT006) and the Department of Education of Henan Province (No. 2008 A150013).

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds