5-(4-Bromo­phen­oxy)-1-methyl-3-methyl-1H-pyrazole-4-carbaldehyde-O-[(5-meth­oxy-1,3,4-thia­diazol-2-yl)-meth­yl]oxime

Fan, C.-G.; Chen, J.-C.; Dai, H.; Wei, Y.-H.; Shi, Y.-J.

doi:10.1107/S1600536812042274

Volume 68
Part 11
Page o3122
November 2012

Received 7 October 2012
Accepted 9 October 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.004 Å
R = 0.029
wR = 0.054
Data-to-parameter ratio = 13.3
Details

5-(4-Bromophenoxy)-1-methyl-3-methyl-1H-pyrazole-4-carbaldehyde-O-[(5-methoxy-1,3,4-thiadiazol-2-yl)-methyl]oxime

Chong-Guang Fan,^a Jian-Cun Chen,^a Hong Dai,^a ^* Yun-Hua Wei ^a and Yu-Jun Shi ^a ^*

^aCollege of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, Peoples' Republic of China
Correspondence e-mail: gaofz2005@yahoo.com.cn, yjshi2001@yahoo.com.cn

In the title molecule, C₁₆H₁₆BrN₅O₃S, the 1,3,4-thiadiazole ring is situated under the benzene ring, forming a dihedral angle of 86.6 (2)°, and with an SCg (where Cg is the centroid of the benzene ring) distance of 3.312 (3) Å. The benzene and 1,3,4-thiadiazole rings form dihedral angles of 83.8 (3) and 57.7 (2)°, respectively, with the central pyrazole ring. In the absence of classical hydrogen bonds, the crystal packing is stabilized by a C-H [pi] interaction..

Related literature

For a related structure, see: Dai et al. (2011).

Experimental

Crystal data

C₁₆H₁₆BrN₅O₃S
M_r = 438.31
Triclinic, $[P \overline 1]$
a = 9.732 (3) Å
b = 9.832 (2) Å
c = 11.166 (3) Å
= 64.55 (2)°
= 69.62 (2)°
= 75.33 (3)°
V = 897.5 (4) Å³
Z = 2
Mo K radiation
= 2.43 mm^-1
T = 113 K
0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008) T_min = 0.642, T_max = 0.759
7729 measured reflections
3175 independent reflections
2363 reflections with I > 2(I)
R_int = 0.044

Refinement

R[F² > 2(F²)] = 0.029
wR(F²) = 0.054
S = 1.02
3175 reflections
238 parameters
H-atom parameters constrained
_max = 0.36 e Å^-3
_min = -0.49 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1-C6 ring.

D-HA	D-H	HA	DA	D-HA
C11-H11ACgⁱ	0.98	2.89	3.652 (4)	125
Symmetry code: (i) -x+2, -y+2, -z+2.

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CV5348 ).

Acknowledgements

This work was supported by the Science and Technology Projects Fund of Nantong City (Nos. K2010016, AS2010005 and AS2011011), the Science Foundation of Nantong University (grant No. 11Z046) and the Science Foundation of Nantong University Xinglin College (grant No. 2010 K132).

References

Dai, H., Miao, W.-K., Wu, S.-S., Qin, X. & Fang, J.-X. (2011). Acta Cryst. E67, o775.
Rigaku (2008). CrystalClear. Rigaku Corporation, Toyko, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds