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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 [sigma](C-C) = 0.004 Å
R = 0.029
wR = 0.054
Data-to-parameter ratio = 13.3
Details
Open access

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

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 S...Cg (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[Dai, H., Miao, W.-K., Wu, S.-S., Qin, X. & Fang, J.-X. (2011). Acta Cryst. E67, o775.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16BrN5O3S

  • Mr = 438.31

  • Triclinic, [P \overline 1]

  • a = 9.732 (3) Å

  • b = 9.832 (2) Å

  • c = 11.166 (3) Å

  • [alpha] = 64.55 (2)°

  • [beta] = 69.62 (2)°

  • [gamma] = 75.33 (3)°

  • V = 897.5 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Rigaku (2008). CrystalClear. Rigaku Corporation, Toyko, Japan.]) Tmin = 0.642, Tmax = 0.759

  • 7729 measured reflections

  • 3175 independent reflections

  • 2363 reflections with I > 2[sigma](I)

  • Rint = 0.044

Refinement
  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.054

  • S = 1.02

  • 3175 reflections

  • 238 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.49 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
C11-H11A...Cgi 0.98 2.89 3.652 (4) 125
Symmetry code: (i) -x+2, -y+2, -z+2.

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Toyko, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CSD] [CrossRef] [details]
Rigaku (2008). CrystalClear. Rigaku Corporation, Toyko, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3122  [ doi:10.1107/S1600536812042274 ]

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