(E)-4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino­meth­yl]phenyl 4-bromo­benzene­sulfonate

Han, J.-R.; Tian, X.; Zhen, X.-L.; Li, Z.-C.; Liu, S.-X.

doi:10.1107/S1600536808035034

Volume 64
Part 11
Page o2244
November 2008

Received 27 October 2008
Accepted 28 October 2008
Online 31 October 2008

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.006 Å
R = 0.044
wR = 0.107
Data-to-parameter ratio = 13.9
Details

(E)-4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)iminomethyl]phenyl 4-bromobenzenesulfonate

Jian-Rong Han,^a ^* Xia Tian,^a Xiao-Li Zhen,^a Zhen-Chao Li ^a and Shou-Xin Liu ^b ⁺

^aCollege of Sciences, Hebei University of Science & Technology, Shijiazhuang 050018, People's Republic of China, and ^bCollege of Chemical & Pharmaceutical Engineering, Hebei University of Science & Technology, Shijiazhuang 050018, People's Republic of China
Correspondence e-mail: han_jianrong@163.com

In the title compound, C₂₄H₂₀BrN₃O₄S, the central benzene ring makes dihedral angles of 17.13 (13), 39.83 (13) and 58.37 (13)°, respectively, with the pyrazolone ring, the bromobenzene ring and the terminal phenyl ring. In the crystal structure, the packing is stabilized by a weak non-classical intermolecular C-HO hydrogen bond which links the molecules into a chain propagating in [100].

Related literature

For a related structure, see: Han et al. (2007). For general background, see: Kahwa et al. (1986); Klayman et al. (1979); Santos et al. (2001). For reference geometrical data: see: Allen et al. (1987).

Experimental

Crystal data

C₂₄H₂₀BrN₃O₄S
M_r = 526.40
Monoclinic, P 2₁ /n
a = 6.9959 (14) Å
b = 33.222 (6) Å
c = 10.218 (2) Å
= 95.992 (3)°
V = 2361.9 (8) Å³
Z = 4
Mo K radiation
= 1.86 mm^-1
T = 294 (2) K
0.18 × 0.16 × 0.11 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.693, T_max = 0.815
12151 measured reflections
4174 independent reflections
2506 reflections with I > 2(I)
R_int = 0.058

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.107
S = 1.01
4174 reflections
300 parameters
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C17-H17AO4ⁱ	0.96	2.40	3.361 (5)	176
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; 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: HB2828 ).

Acknowledgements

The project was supported by the Foundation of the Education Department of Hebei Province (grant No. 606022).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Han, J.-R., Zhen, X.-L., Tian, X., Li, F. & Liu, S.-X. (2007). Acta Cryst. E63, o4035.
Kahwa, I. A., Selbin, J., Hsieh, T. C.-Y. & Laine, R. A. (1986). Inorg. Chim. Acta, 118, 179-185.
Klayman, D. L., Bartosevich, J. F., Griffin, T. S., Mason, C. J. & Scovill, J. P. (1979). J. Med. Chem. 22, 855-862.
Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838-844.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds