4-[(tert-Butyl­diphenyl­sil­yloxy)meth­yl]pyridazin-3(2H)-one

María Carmen Costas-Lago; Tamara Costas; Noemí Vila; Pedro Besada

doi:10.1107/S1600536813032212

. 2013 Nov 30;69(Pt 12):o1859–o1860. doi: 10.1107/S1600536813032212

4-[(tert-Butyldiphenylsilyloxy)methyl]pyridazin-3(2H)-one

María Carmen Costas-Lago ^a, Tamara Costas ^a, Noemí Vila ^a, Pedro Besada ^a,^*

PMCID: PMC4004440 PMID: 24860296

Abstract

In the title compound, C₂₁H₂₄N₂O₂Si, the carbonyl group of the heterocyclic ring and the O atom of the silyl ether group are placed toward opposite sides and the tert-butyl and pyridazinone moieties are anti-oriented across the Si—O bond [torsion angle = −168.44 (19)°]. In the crystal, molecules are assembled into inversion dimers through co-operative N—H⋯O hydrogen bonds between the NH groups and O atoms of the pyridazinone rings of neighbouring molecules. The dimers are linked by π–π interactions involving adjacent pyridazinone rings [centroid–centroid distance = 3.8095 (19) Å], generating ladder-like chains along the b-axis direction. The chains are further linked into a two-dimensional network parallel to the ab plane through weak C—H⋯π interactions.

Related literature

For background to pyridazinone analogues displaying biological activities, see: Siddiqui et al. (2010 ▶); Costas et al. (2010 ▶); Abouzid & Bekhit (2008 ▶); Cesari et al. (2006 ▶); Rathish et al. (2009 ▶); Al-Tel (2010 ▶); Suree et al. (2009 ▶); Tao et al. (2011 ▶). For related structures, see: Costas et al. (2010 ▶); Costas-Lago et al. (2013 ▶).

Experimental

Crystal data

C₂₁H₂₄N₂O₂Si
M _r = 364.51
Monoclinic,
a = 10.774 (4) Å
b = 7.988 (3) Å
c = 24.681 (10) Å
β = 100.207 (7)°
V = 2090.5 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 293 K
0.48 × 0.41 × 0.23 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.707, T _max = 0.746
25187 measured reflections
5045 independent reflections
3076 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.148
S = 1.00
5045 reflections
242 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813032212/lr2118sup1.cif

e-69-o1859-sup1.cif^{(28.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032212/lr2118Isup2.hkl

e-69-o1859-Isup2.hkl^{(247.1KB, hkl)}

Click here for additional data file.^{(7KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813032212/lr2118Isup3.cml

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

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

Cg2 is the centroid of the C8′–C13′ ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3ⁱ	0.93 (3)	1.84 (3)	2.764 (2)	176 (2)
C6—H6⋯Cg2ⁱⁱ	0.93	2.76	3.637 (3)	138

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

Acknowledgments

This work was financially supported by the Xunta de Galicia (CN 2012/184). The authors gratefully acknowledge Dr Berta Covelo, X-ray Diffraction service of the University of Vigo, for her valuable assistance. MCC-L and NV thank the University of Vigo for their Master and PhD fellowships, respectively.

supplementary crystallographic information

1. Introduction

Pyridazin-3(2H)-one derivatives possess a wide range of biological activities, this fact together with the easy functionalization at various ring positions makes the pyridazinone nucleus a versatile pharmacophore to design and synthesize new drugs. For instance, an important number of pyridazinones have been reported as antihypertensive (Siddiqui et al., 2010), antiplatelet (Costas et al., 2010), anti-inflammatory (Abouzid & Bekhit, 2008), antinociceptive (Cesari et al., 2006), antidiabetic (Rathish et al., 2009), anticancer (Al-Tel, 2010), antimicrobial (Suree et al., 2009) or anti-histamine H₃ agents (Tao et al., 2011).

2. Experimental

2.1. Synthesis and crystallization

A solution of 3-(tert-butyldiphenylsilyloxymethyl)-5-hydroxy-5H-furan-2-ona (50 mg, 0.136 mmol) and hydrazine monohydrate (14 ml, 0.284 mmol) in ethanol (2 ml) was stirred at reflux for 4 h. The solvent was evaporated under reduced pressure and residue was purified by column chromatography on silica gel (hexane/ethyl acetate 4:1) to afford a colourless oil (16 mg, 32%). Single crystals suitable for X-ray analysis were grown from a chloroform solution at room temperature.

2.2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. All H-atoms were positioned and refined using a riding model with d(C—H)= 0.93 Å, U_iso = 1.2U_eq(C) for aromatic C—H groups,d(C—H)= 0.97 Å, U_iso = 1.2U_eq(C) for CH₂ group and d(C—H)= 0.96 Å, U_iso = 1.5U_eq(C) for CH₃ group; except for the hydrogen atoms of the NH group which were located from a Fourier-difference map and refined isotropically

3. Results and discussion

The compound I, an isomer of the 5-(tert-butyldiphenylsilyloxymethyl)pyridazin-3(2H)-one (Costas-Lago et al., 2013), was prepared in order to develop new pyridazinone analogues C4-substituted as antiplatelet agents. In the titled compound, the carbonyl group of the heterocyclic ring and the oxygen atom of the silyl ether group are placed toward opposite sides, this contrasts with the geometry found in the C5-substituted regioisomer and could explain the nearly flat disposition of the sequence C4—C1'-O1'-Si, with a torsion angle of -174.30 (15)°. The pyridazinone ring forms dihedral angles of 89.10 (8)° and 77.53 (7)°, respectively, with the C2'-C7' and C8'-C13' benzene rings, while the dihedral angle between both benzene rings is 48.41 (10)°.

The geometry of titled compound lets the assembly of molecules in supramolecular organizations based on hydrogen bonding, π–π and CH···π interactions. The cooperative N—H···O hydrogen bonds between the NH group of one pyridazinone ring and the oxygen atom of an adjacent ring form supramolecular dimers (Figure 2). These dimers are joined by π–π interactions involving also neighbouring pyridazinone rings [Cg(1): N1—N2—C3—C4—C5—C6; d[Cg(1)—Cg(1)ⁱⁱ]: 3.8095 (19) Å; d[Cg(1)···P(1)ⁱⁱ]: 3.4279 (8) Å; α: 0°; symmetry code ii: 1 - x, 2 - y, -z] resulting in a ladder chain along the crystallographic b axis (Figure 3). Finally, the linear chains are linked into a two-dimensional network through weak C—H···π interactions (Figure 4) involving CH groups of the pyridazinone rings and phenyl rings from neighbouring chains [C6—H6···Cg(2)ⁱⁱⁱ; Cg(2): C8'-C9'-C10'-C11'-C12'-C13'; d[H···Cg(2)ⁱⁱⁱ]: 2.890 Å; γ: 17.60°; symmetry code iii: 2 - x, -2 - y, -z]. In this case the pyridazinone ring arrangement prevents the three-dimensional growth observed in the C5-substituted regioisomer (Costas-Lago et al., 2013).