Dimethyl 1-(3-cyano­benz­yl)-1H-pyrazole-3,5-dicarboxyl­ate

Xiao, J.; Yao, J.-Y.; Zhao, H.

doi:10.1107/S1600536809014895

Volume 65
Part 5
Page o1132
May 2009

Received 14 April 2009
Accepted 22 April 2009
Online 25 April 2009

Key indicators
Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.003 Å
R = 0.056
wR = 0.147
Data-to-parameter ratio = 16.6
Details

Dimethyl 1-(3-cyanobenzyl)-1H-pyrazole-3,5-dicarboxylate

Jie Xiao,^a Ji-Yuan Yao ^a and Hong Zhao ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical, Engineering, Southeast University, Nanjing 210096, People's Republic of China
Correspondence e-mail: zhaohong@seu.edu.cn

In the molecule of the title compound, C₁₅H₁₃N₃O₄, the dihedral angle between the pyrazole and benzene ring planes is 67.7 (1)°. The crystal structure is stabilized by an intramolecular C-HO hydrogen bond and two weak intermolecular C-HO interactions.

Related literature

For the biological activity of pyrazoles, see: Lee et al. (1989); Chambers et al. (1985). For the importance of nitrile derivatives in the synthesis of some heterocyclic molecules, see: Radl et al. (2000). For related structures, see: Fu & Zhao (2007); Xiao & Zhao (2008a,b,c).

Experimental

Crystal data

C₁₅H₁₃N₃O₄
M_r = 299.28
Triclinic, $[P \overline 1]$
a = 8.783 (3) Å
b = 9.538 (4) Å
c = 9.999 (4) Å
= 68.42 (3)°
= 71.79 (4)°
= 82.13 (4)°
V = 739.7 (5) Å³
Z = 2
Mo K radiation
= 0.10 mm^-1
T = 292 K
0.40 × 0.30 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.968, T_max = 0.979
7555 measured reflections
3338 independent reflections
2093 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.056
wR(F²) = 0.147
S = 1.05
3338 reflections
201 parameters
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C15-H15BO1ⁱ	0.96	2.43	3.363 (3)	163
C9-H9O1ⁱⁱ	0.93	2.53	3.348 (3)	147
C6-H6AO4	0.97	2.41	2.979 (3)	117
Symmetry codes: (i) x, y-1, z; (ii) -x, -y+1, -z+1.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008); program(s) used to refine structure: SHELXTL/PC; molecular graphics: SHELXTL/PC; software used to prepare material for publication: SHELXTL/PC.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2204 ).

Acknowledgements

This work was supported financially by the Southeast University Fund for Young Researchers (4007041027).

References

Chambers, D., Denny, W. A., Buckleton, J. S. & Clark, G. R. (1985). J. Org. Chem. 50, 4736-4738.
Fu, D.-W. & Zhao, H. (2007). Acta Cryst. E63, o3206.
Lee, H. H., Cain, B. F., Denny, W. A., Buckleton, J. S. & Clark, G. R. (1989). J. Org. Chem. 54, 428-431.
Radl, S., Hezky, P., Konvicka, P. & Krejci, J. (2000). Collect. Czech. Chem. Commun. 65, 1093-1108.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Xiao, J. & Zhao, H. (2008a). Acta Cryst. E64, o965.
Xiao, J. & Zhao, H. (2008b). Acta Cryst. E64, o986.
Xiao, J. & Zhao, H. (2008c). Acta Cryst. E64, o1436.

organic compounds