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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 [sigma](C-C) = 0.003 Å
R = 0.056
wR = 0.147
Data-to-parameter ratio = 16.6
Details
Open access

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

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-H...O hydrogen bond and two weak intermolecular C-H...O interactions.

Related literature

For the biological activity of pyrazoles, see: Lee et al. (1989[Lee, H. H., Cain, B. F., Denny, W. A., Buckleton, J. S. & Clark, G. R. (1989). J. Org. Chem. 54, 428-431.]); Chambers et al. (1985[Chambers, D., Denny, W. A., Buckleton, J. S. & Clark, G. R. (1985). J. Org. Chem. 50, 4736-4738.]). For the importance of nitrile derivatives in the synthesis of some heterocyclic molecules, see: Radl et al. (2000[Radl, S., Hezky, P., Konvicka, P. & Krejci, J. (2000). Collect. Czech. Chem. Commun. 65, 1093-1108.]). For related structures, see: Fu & Zhao (2007[Fu, D.-W. & Zhao, H. (2007). Acta Cryst. E63, o3206.]); Xiao & Zhao (2008a[Xiao, J. & Zhao, H. (2008a). Acta Cryst. E64, o965.],b[Xiao, J. & Zhao, H. (2008b). Acta Cryst. E64, o986.],c[Xiao, J. & Zhao, H. (2008c). Acta Cryst. E64, o1436.]).

[Scheme 1]

Experimental

Crystal data
  • C15H13N3O4

  • Mr = 299.28

  • Triclinic, [P \overline 1]

  • a = 8.783 (3) Å

  • b = 9.538 (4) Å

  • c = 9.999 (4) Å

  • [alpha] = 68.42 (3)°

  • [beta] = 71.79 (4)°

  • [gamma] = 82.13 (4)°

  • V = 739.7 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.968, Tmax = 0.979

  • 7555 measured reflections

  • 3338 independent reflections

  • 2093 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.147

  • S = 1.05

  • 3338 reflections

  • 201 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C15-H15B...O1i 0.96 2.43 3.363 (3) 163
C9-H9...O1ii 0.93 2.53 3.348 (3) 147
C6-H6A...O4 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[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CrossRef] [ChemPort]
Fu, D.-W. & Zhao, H. (2007). Acta Cryst. E63, o3206.  [CSD] [CrossRef] [details]
Lee, H. H., Cain, B. F., Denny, W. A., Buckleton, J. S. & Clark, G. R. (1989). J. Org. Chem. 54, 428-431.  [CrossRef] [ChemPort]
Radl, S., Hezky, P., Konvicka, P. & Krejci, J. (2000). Collect. Czech. Chem. Commun. 65, 1093-1108.  [ISI] [CrossRef] [ChemPort]
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Xiao, J. & Zhao, H. (2008a). Acta Cryst. E64, o965.  [CSD] [CrossRef] [details]
Xiao, J. & Zhao, H. (2008b). Acta Cryst. E64, o986.  [CSD] [CrossRef] [details]
Xiao, J. & Zhao, H. (2008c). Acta Cryst. E64, o1436.  [CSD] [CrossRef] [details]


Acta Cryst (2009). E65, o1132  [ doi:10.1107/S1600536809014895 ]

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