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

Jian-Rong Han; Xia Tian; Xiao-Li Zhen; Zhen-Chao Li; Shou-Xin Liu

doi:10.1107/S1600536808035034

. 2008 Oct 31;64(Pt 11):o2244. doi: 10.1107/S1600536808035034

(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, Shou-Xin Liu ^b,^‡

PMCID: PMC2959600 PMID: 21581098

Abstract

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—H⋯O 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,
a = 6.9959 (14) Å
b = 33.222 (6) Å
c = 10.218 (2) Å
β = 95.992 (3)°
V = 2361.9 (8) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.058

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.107
S = 1.01
4174 reflections
300 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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 Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808035034/hb2828sup1.cif

e-64-o2244-sup1.cif^{(23.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035034/hb2828Isup2.hkl

e-64-o2244-Isup2.hkl^{(204.6KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯O4ⁱ	0.96	2.40	3.361 (5)	176

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

The synthesis and structure of Schiff bases have attracted much attention in biology and chemistry (Kahwa et al., 1986; Klayman et al., 1979). Many Schiff base derivatives have been synthesized and employed to develop protein and enzyme mimics (Santos et al., 2001). Among the large number of compounds, 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one forms a variety of Schiff bases with aldehydes, and the synthesis and crystal structures of some of them, such as (E)-4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylimino) methyl]-phenyl 4-chlorobenzoate (Han et al., 2007) has been reported.

As part of an investigation of the potential coordination properties of Schiff bases that could function as ligands, we now report the synthesis and structure of the title compound, (I).

In the title molecule (Fig. 1), the pyrazolone ring (C14—C16/N1/N2/N3/O4) is nearly planar, with an r.m.s. deviation for fitted atoms of 0.029 Å. It makes a dihedral angle of 50.07 (13)° with its attached phenyl ring (C19—C24). The central benzene ring (C7—C13/O3) is almost planar, with an r.m.s. deviation for fitted atoms of 0.040Å. This group makes dihedral angles of 17.13 (13)°, 39.83 (13)° and 58.37 (13)°, respectively, with the the pyrazolone ring (C14—C16/N1/N2/N3/O4), the terminal C1—C6 benzene ring and the terminal C19—C24 phenyl ring. Otherwise, all bond lengths and angles are within their normal ranges (Allen et al., 1987).

In the crystal, the packing is stabilized by a weak, non-classical intermolecular C17—H17A···O4 hydrogen bond that links molecules into one-dimensional extended chains running along the a axis (Table 1, Fig. 2).

Experimental

An anhydrous ethanol solution (50 ml) of 4-formylphenyl 4-bromobenzenesulfonate (3.41 g, 10 mmol) was added to an anhydrous ethanol solution (50 ml) of 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one (2.03 g, 10 mmol) and the mixture stirred at 350 K for 3 h under N₂, giving a yellow precipitate. The product was isolated, recrystallized from acetonitrile, and then dried in a vacuum to give pure compound (I) in 87% yield. Yellow blocks of (I) were obtained by slow evaporation of an acetonitrile solution.