Ethyl 1-benzyl-3-(4-bromo­phen­yl)-1H-pyrazole-5-carboxyl­ate

Jia, J.; Yang, H.; Ge, Y.Q.; Wang, J.W.

doi:10.1107/S1600536811024986

Volume 67
Part 8
Page o1918
August 2011

Received 17 June 2011
Accepted 25 June 2011
Online 6 July 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.034
wR = 0.088
Data-to-parameter ratio = 14.2
Details

Ethyl 1-benzyl-3-(4-bromophenyl)-1H-pyrazole-5-carboxylate

Jiong Jia,^a ^* He Yang,^a Yan Qing Ge ^a and Jian Wu Wang ^a

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China
Correspondence e-mail: yqge@yahoo.cn

In the title compound, C₁₉H₁₇BrN₂O₂, the pyrazole ring makes dihedral angles of 88.00 (16) and 5.78 (13)° with the phenyl and bromophenyl rings, respectively. In the crystal, molecules are linked by weak intermolecular C-HO hydrogen bonds.

Related literature

For the pharmacological activity of pyrazole compounds and applications of nitrogen-containing heterocyclic compounds, see: Ge et al. (2009, 2011). For the related structures, see: Han et al. (2011); Ge et al. (2007); Li et al. (2011).

Experimental

Crystal data

C₁₉H₁₇BrN₂O₂
M_r = 385.26
Monoclinic, P 2₁ /n
a = 10.5656 (13) Å
b = 15.3433 (19) Å
c = 11.5706 (14) Å
= 111.506 (2)°
V = 1745.1 (4) Å³
Z = 4
Mo K radiation
= 2.37 mm^-1
T = 298 K
0.22 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.624, T_max = 0.764
8955 measured reflections
3089 independent reflections
2332 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.088
S = 1.02
3089 reflections
217 parameters
H-atom parameters constrained
_max = 0.33 e Å^-3
_min = -0.70 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C16-H16O1ⁱ	0.93	2.50	3.369 (4)	155
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2438 ).

Acknowledgements

The authors are very grateful to Li Jikun (Taishan College) for his invaluable support.

References

Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Ge, Y.-Q., Dong, W.-L., Xia, Y., Wei, F. & Zhao, B.-X. (2007). Acta Cryst. E63, o1313-o1314.
Ge, Y. Q., Jia, J., Li, Y., Yin, L. & Wang, J. W. (2009). Heterocycles, 42, 197-206.
Ge, Y. Q., Jia, J., Yang, H., Tao, X. T. & Wang, J. W. (2011). Dyes Pigments, 88, 344-349.
Han, Z., Zheng, H.-L. & Tian, X.-L. (2011). Acta Cryst. E67, o511.
Li, Y.-Q., Jia, B.-X., Xiao, Y.-L. & Guo, F.-G. (2011). Acta Cryst. E67, o468.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds