2-[5-(1,3-Benzodioxol-5-yl)-3-ferrocenyl-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia­zole

Liu, W.-Y.; Xie, Y.-S.; Wang, B.-S.; Zhao, B.-X.

doi:10.1107/S160053681003638X

Volume 66
Part 10
Page m1275
October 2010

Received 27 August 2010
Accepted 11 September 2010
Online 18 September 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R = 0.050
wR = 0.124
Data-to-parameter ratio = 14.5
Details

2-[5-(1,3-Benzodioxol-5-yl)-3-ferrocenyl-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thiazole

Wei-Yong Liu,^a Yong-Sheng Xie,^b Bai-Shan Wang ^a and Bao-Xiang Zhao ^a ^*

^aInstitute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China, and ^bDepartment of Chemical and Environment Engineering, Chongqing Three Gorges University, Chongqing 404100, People's Republic of China
Correspondence e-mail: bxzhao@sdu.edu.cn

In the title compound, [Fe(C₅H₅)(C₂₄H₁₈N₃O₂S)], the pyrazoline ring adopts a twist conformation. The thiazole ring forms dihedral angles of 83.7 (2) and 34.4 (2)° with the benzene ring of the benzodioxole ring and the fused phenyl ring, respectively. The molecular conformation is stabilized by an intramolecular C-H [pi] interaction. The crystal packing features intermolecular C-HN, C-HO hydrogen bonds and weak C-H [pi] interactions.

Related literature

For the biological activity of ferrocenyl derivatives, see: Jaouen et al. (2004); Xie et al. (2008, 2010). For the crystal structures of pyrazoline derivatives, see: Gong et al. (2010). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

[Fe(C₅H₅)(C₂₄H₁₈N₃O₂S)]
M_r = 533.41
Triclinic, $[P \overline 1]$
a = 10.228 (5) Å
b = 11.018 (5) Å
c = 12.604 (6) Å
= 107.776 (8)°
= 100.416 (8)°
= 112.767 (7)°
V = 1172.7 (10) Å³
Z = 2
Mo K radiation
= 0.77 mm^-1
T = 293 K
0.15 × 0.10 × 0.10 mm

Data collection

Bruker SMART area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.894, T_max = 0.927
6579 measured reflections
4716 independent reflections
3140 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.124
S = 1.02
4716 reflections
325 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C13-C18, C25-C29, C1-C6 and C20-C24 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C15-H15N3ⁱ	0.93	2.49	3.402 (6)	168
C28-H28O2ⁱⁱ	0.98	2.43	3.337 (6)	153
C22-H22Cg1ⁱⁱⁱ	0.98	2.97	3.709 (5)	133
C26-H26Cg1	0.98	2.90	3.844 (5)	163
C5-H5Cg2^iv	0.93	2.91	3.658 (5)	138
C8-H8Cg3^v	0.93	2.98	3.590 (4)	125
C11-H11ACg4^vi	0.97	2.85	3.670 (4)	142
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z+2; (iii) x-1, y, z; (iv) x, y-1, z-1; (v) -x+1, -y, -z; (vi) -x, -y, -z+1.

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2480 ).

Acknowledgements

This study was supported by the Natural Science Foundation of Shandong Province (Z2008B10).

References

Bruker (2004). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Gong, Z. L., Zheng, L. W., Zhao, B. X., Yang, D. Z., Lv, H. S., Liu, W. Y. & Lian, S. (2010). J. Photochem. Photobiol. A, 209, 49-55.
Jaouen, G., Top, S., Vessireres, A., Leclercq, G., Vaissermann, J. & McGlinchey, M. J. (2004). Curr. Med. Chem. 11, 2505-2517.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Xie, Y. S., Pan, X. H., Zhao, B. X., Liu, J. T., Shin, D. S., Zhang, J. H., Zheng, L. W., Zhao, J. & Miao, J. Y. (2008). J. Organomet. Chem. 693, 1367-1374.
Xie, Y. S., Zhao, H. L., Su, H., Zhao, B. X., Liu, J. T., Li, J. K., Lv, H. S., Wang, B. S., Shin, D. S. & Miao, J. Y. (2010). Eur. J. Med. Chem. 45, 210-218.

metal-organic compounds