3,5-Bis[1-acetyl-5-(4-chloro­phen­yl)-4,5-dihydro-1H-pyrazol-3-yl]-2,6-dimethyl­pyridine

Qun Qian; Jun Zhang; Min Zhang; Xiang He; Yi-Ben Xia

doi:10.1107/S1600536808023921

. 2008 Aug 6;64(Pt 9):o1700. doi: 10.1107/S1600536808023921

3,5-Bis[1-acetyl-5-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-3-yl]-2,6-dimethylpyridine

Qun Qian ^a, Jun Zhang ^a, Min Zhang ^a,^*, Xiang He ^a, Yi-Ben Xia ^b

PMCID: PMC2960675 PMID: 21201689

Abstract

The title compound, C₂₉H₂₇Cl₂N₅O₂, contains a central pyridine ring and two functionalized pyrazoline rings. The pyridine ring and the two attached pyrazoline rings are nearly coplanar, whereas the terminal chlorophenyl rings are nearly perpendicular to the attached pyrazoline rings [dihedral angles = 86.78 (1) and 77.70 (1)°]. Molecules are linked by weak intermolecular C—H⋯O hydrogen bonding.

Related literature

For general background, see: Ahn et al. (2004 ▶); Palaska et al. (1996 ▶); Yar et al. (2006 ▶)

Experimental

Crystal data

C₂₉H₂₇Cl₂N₅O₂
M _r = 548.46
Monoclinic,
a = 12.345 (3) Å
b = 9.6763 (19) Å
c = 13.268 (3) Å
β = 115.00 (3)°
V = 1436.4 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 296 (2) K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.926, T _max = 0.950
7509 measured reflections
3736 independent reflections
2520 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.077
S = 0.91
3736 reflections
344 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.15 e Å⁻³
Absolute structure: Flack (1983 ▶), 1031 Friedel pairs
Flack parameter: 0.06 (6)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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 Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808023921/xu2444sup1.cif

e-64-o1700-sup1.cif^{(25.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023921/xu2444Isup2.hkl

e-64-o1700-Isup2.hkl^{(183.1KB, 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
C9—H9A⋯O2ⁱ	0.99	2.59	3.358 (3)	135
C17—H17A⋯O2ⁱⁱ	0.95	2.50	3.359 (4)	151

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank the Instrument Analysis and Research Center of Shanghai University for the data collection. The project was supported by the Key Subject of Shanghai Municipal Education Commission (grant No. J50102) and the Foundation of the Education Commission of Shanghai Municipality, China (grant No. 08zz44).

supplementary crystallographic information

Comment

The pyrazoline derivatives are well known nitrogen-containing heterocyclic compounds which show various biological activities and pharmacological properties (Palaska et al., 1996). Some of them can be anti-bacterial and anti-fungal, others are anti-diabetic, anti-inflammatory and also active against many Mycobacterias (Ahn et al., 2004; Yar et al., 2006). As the stereochemistry may be an important modulator of biological activity, the crystal structure of the title compound has been determined.

The molecular structure is shown in Fig. 1. There are two chlorophenyl rings bonded with two pyrazoline rings in cis-arrangement, and these two pyrazoline rings are further bonded with the same pyridine ring. The central pyridine ring and two attached pyrazoline rings are nearly coplanar with the dihedral angles of 1.32 (2) and 4.88 (2)°, whereas the dihedral angles between each chlorophenyl plane and the attached pyrazoline planes are 86.78 (1) and 77.70 (1)°.

In the crystal structure, there are weak intermolecular C—H···O hydrogen bonding (Table 1 and Fig. 2).

Experimental

2,6-Dimethyl-3,5-di-[3-(4-chloro-phenyl)-acryloyl-pyridine (1 mmol, 0.436 g) and 85% hydrazine hydrate solution (4 mmol, 0.235 g) were dissolved in 5 ml of acetic acid solution. The solution was refluxed for 8 h, and allowed to cool to room temperature. The reaction mixture was poured into crushed ice, then neutralized with dilute sodium hydroxide solution. The solid separated was filtered off, washed with water, dried and recrystallized from ethyl acetate to give a colorless compound in a yield of of 40%. Single crystals suitable for X-ray analysis were obtained form tetrahydrofuran at room temperature.