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

Qun Qian; Jun Zhang; Min Zhang; Xiang He; YiBen Xia

doi:10.1107/S1600536808018497

. 2008 Jun 25;64(Pt 7):o1334. doi: 10.1107/S1600536808018497

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

Qun Qian ^a, Jun Zhang ^a, Min Zhang ^a,^*, Xiang He ^a, YiBen Xia ^b

PMCID: PMC2961714 PMID: 21202958

Abstract

In the title compound, C₂₉H₂₇Cl₂N₅O₂·C₄H₈O, the polycyclic system is composed of three parts: one central pyridine ring substituted by two functionalized pyrazoline rings. The dihedral angles between the central pyridine plane and pyrazoline planes are 5.11 (1) and 13.99 (1)°, whereas the dihedral angles between each chlorophenyl plane and the attached pyrazoline planes are 88.65 (1) and 83.87 (1)°. Molecules are linked by intermolecular C—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For related literature, see: Holla et al. (2002 ▶); Palaska et al. (1996 ▶); Soudi et al. (2005 ▶); Chopra et al.(2006 ▶).

Experimental

Crystal data

C₂₉H₂₇Cl₂N₅O₂·C₄H₈O
M _r = 620.56
Monoclinic,
a = 16.888 (3) Å
b = 11.180 (2) Å
c = 17.313 (4) Å
β = 98.69 (3)°
V = 3231.5 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 (2) K
0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.953, T _max = 0.976
16422 measured reflections
5715 independent reflections
2714 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.171
S = 0.95
5715 reflections
393 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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/S1600536808018497/bh2175sup1.cif

e-64-o1334-sup1.cif^{(27.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018497/bh2175Isup2.hkl

e-64-o1334-Isup2.hkl^{(279.8KB, 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—H9B⋯O3	0.97	2.49	3.423 (7)	163
C21—H21B⋯O1ⁱ	0.97	2.57	3.211 (4)	123
C9—H9A⋯O1ⁱ	0.97	2.35	3.234 (4)	151
C23—H23A⋯O2ⁱⁱ	0.96	2.45	3.385 (4)	166

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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 XRD data analysis. 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 (grant No. 08zz44).

supplementary crystallographic information

Comment

Nitrogen-containing heterocycles compounds are well known natural products moieties which present interesting biological activities and pharmacological properties (Holla et al., 2002; Soudi et al., 2005). For example, 1,3,5-trisubstitituted pyrazolines show reversible and selective monoamine oxidase inhibitory properties. Their selective biological activity is in part due to the influence of substitution on the compounds conformation (Palaska et al., 1996). These useful applications for the 1,3,5-trisubstituted pyrazolines attracted our attention and we present here a new member of this family.

The molecular structure of (I) consists of one polycyclic molecule and one tetrahydrofuran solvent molecule (Fig. 1). There are two substituted phenyl rings bonded with two different pyrazoline rings, and these two pyrazoline rings are further bonded with one central pyridine ring. The dihedral angles between the pyridine plane and the two pyrazoline planes are 5.10 and 13.99°. Each substituted phenyl plane is nearly normal to the corresponding pyrazoline plane, with dihedral angles of 88.04 and 83.38°. Bond lengths in the pyrazoline rings and substituted phenyl rings are in good agreement with those found in similar compounds (e.g. Chopra et al., 2006).

In the crystal structure, there are three types of intermolecular and one intramolecular hydrogen bonds, which make the crystal structure to be more stable (see hydrogen-bond geometry Table).

Experimental

2,6-Dimethyl-3,5-di-[3-(4-chlorophenyl)-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. The mixture was refluxed for 8 h, and then allowed to cool to room temperature. The reaction mixture was poured into crushed ice, and neutralized with diluted NaOH solution. The solid separated was filtered off, washed with water, dried and recrystallized from ethyl acetate, to give a colourless compound in a yield of of 42% (m.p. 489–491 K). Single crystals suitable for X-ray analysis were obtained form tetrahydrofuran at room temperature.