2-[2-(4-Benzyl­piperazin-1-ylcarbon­yl)eth­yl]-5,6-diphenyl­pyridazin-3(2H)-one

Abdullah Aydın; Deniz S Doğruer; Mehmet Akkurt; Orhan Büyükgüngör

doi:10.1107/S1600536808013159

. 2008 May 10;64(Pt 6):o1030. doi: 10.1107/S1600536808013159

2-[2-(4-Benzylpiperazin-1-ylcarbonyl)ethyl]-5,6-diphenylpyridazin-3(2H)-one

Abdullah Aydın ^a, Deniz S Doğruer ^b, Mehmet Akkurt ^c,^*, Orhan Büyükgüngör ^d

PMCID: PMC2961344 PMID: 21202554

Abstract

The title compound, C₃₀H₃₀N₄O₂, has a non-planar conformation, the dihedral angles formed by the pyridazinone ring plane and the three phenyl rings being 54.61 (7), 51.10 (7) and 59.53 (8)°. The piperazine ring adopts a chair conformation. Inter- and intramolecular C—H⋯O contacts are found in the crystal structure and these consolidate the three-dimensional packing.

Related literature

For related structures, see: Doğruer et al. (2007 ▶); Swenson et al. (1997 ▶); Yüksektepe et al. (2004 ▶). For structure analysis, see: Allen et al. (1987 ▶); Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₃₀H₃₀N₄O₂
M _r = 478.58
Monoclinic,
a = 15.6725 (12) Å
b = 9.1139 (5) Å
c = 17.6743 (12) Å
β = 90.553 (6)°
V = 2524.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.73 × 0.51 × 0.11 mm

Data collection

Stoe IPDS-2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.477, T _max = 0.907
30083 measured reflections
4966 independent reflections
3394 reflections with I > 2σ(I)
R _int = 0.062

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.094
S = 1.03
4966 reflections
325 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808013159/tk2267sup1.cif

e-64-o1030-sup1.cif^{(30.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013159/tk2267Isup2.hkl

e-64-o1030-Isup2.hkl^{(238.3KB, 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
C2—H2⋯O2ⁱ	0.93	2.47	3.3470 (19)	157
C18—H18B⋯O1	0.97	2.56	3.0755 (18)	113
C20—H20B⋯O2	0.97	2.35	2.759 (2)	105

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS-2 diffractometer (purchased under grant F.279 of the University Research Fund).

supplementary crystallographic information

Comment

The title compound (I) was prepared recently (Doğruer et al., 2007) and displays analgesic and anti-inflammatory effects. In the crystal structure of (I), Fig. 1, the bond lengths and angles are within their normal ranges (Allen et al., 1987). The piperazine bridge has a normal chair conformation, with puckering parameters (Cremer & Pople, 1975) Q_T = 0.562 (2) Å, θ = 176.2 (2) ° and φ = 354 (3) °. Relevant literature values for the puckering of the cyclobutane ring are 29.0 (1)° (Yüksektepe et al., 2004) and 23.5° (Swenson et al., 1997). In this study, the N1/N2/C1—C4 pyridazinone ring plane forms dihedral angles of 54.61 (7), 51.10 (7) and 59.53 (8)°, respectively, with the planes of the (A: C5—C10), (B: C11—C16) and (C: C25 –C30) phenyl rings. The dihedral angles between the phenyl rings are A/B = 50.77 (8), A/C = 83.01 (9) and B/C = 70.15 (9)°.

The crystal structure is stabilized by inter and intramolecular C—H···O contacts that stabilize the three-dimensional network (Table 1, Fig. 2).

Experimental

[3-(5,6-Diphenyl-3(2H)-pyridazinone-2-yl)propanoic acid (0.01 mol) in dichloromethane (40 ml) at 273 K (ice-bath) was treated with triethylamine (1 ml) and ethyl chloroformate (0.01 mol). After stirring the reaction mixture at 273 K for 15 min, benzylpiperazine (0.011 mol) was added. The final mixture was stirred at 273–298 K for 24 h and evaporated to dryness. The product was solidified with ice-cold water and crystallized from ethanol (yield 25%, m.p. 422 K). IR v_max(cm^-1) (KBr): 1660 (CO ring), 1635 (CO amide) (Doğruer et al., 2007).