Crystal structure of ethyl 2-{4-[(5-chloro-1-benzo­furan-2-yl)meth­yl]-3-methyl-6-oxo-1,6-di­hydro­pyridazin-1-yl}acetate

Youness Boukharsa; Lahcen El Ammari; Jamal Taoufik; Mohamed Saadi; M’hammed Ansar

doi:10.1107/S2056989015006301

. 2015 Apr 9;71(Pt 5):o291–o292. doi: 10.1107/S2056989015006301

Crystal structure of ethyl 2-{4-[(5-chloro-1-benzofuran-2-yl)methyl]-3-methyl-6-oxo-1,6-dihydropyridazin-1-yl}acetate

Youness Boukharsa ^a,^*, Lahcen El Ammari ^b, Jamal Taoufik ^a, Mohamed Saadi ^b, M’hammed Ansar ^a

PMCID: PMC4420114 PMID: 25995910

Abstract

In the title compound, C₁₈H₁₇ClN₂O₄, the dihedral angle between the benzofuran ring system [maximum deviation 0.014 (2) Å] and the oxopyradizine ring is 73.33 (8)°. The structure is characterized by disorder of the ethyl group, which is split into two parts, with a major component of 0.57 (3), and the acetate carbonyl O atom, which is statistically disordered. In the crystal, the molecules are linked by C—H⋯O interactions, forming a three-dimensional network.

Keywords: crystal structure, pyridazinone derivative, hydrogen bonding

Related literature

For pharmacological activities of pyridazinones, e.g. antimicrobial, see: Boukharsa et al. (2014 ▸); Nagle et al. (2014 ▸); El-Hashash et al. (2014 ▸); Tiryaki et al. (2013 ▸); Csókás et al. (2013 ▸); Asif et al. (2014 ▸); Garkani-Nejad & Poshteh-Shirani (2013 ▸). For biological activities of pyridazinone derivatives and their applications, e.g. as insecticides and herbicides, see: Cao et al. (2003 ▸); Jamet & Piedallu (1975 ▸). For pyridazin-3(2H)-one derivatives, see: Taoufik et al. (1984 ▸); Benchat et al. (1998 ▸); Abourichaa et al. (2003 ▸).

Experimental

Crystal data

C₁₈H₁₇ClN₂O₄
M _r = 360.79
Orthorhombic,
a = 7.9792 (2) Å
b = 8.7460 (2) Å
c = 25.2064 (6) Å
V = 1759.06 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 296 K
0.37 × 0.34 × 0.29 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T _min = 0.589, T _max = 0.746
12689 measured reflections
4925 independent reflections
3350 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.114
S = 1.02
4925 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.34 e Å⁻³
Absolute structure: Flack & Bernardinelli (2000 ▸), 2104 Friedel pairs
Absolute structure parameter: 0.02 (7)

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: publCIF (Westrip, 2010 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015006301/tk5363sup1.cif

e-71-0o291-sup1.cif^{(26.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015006301/tk5363Isup2.hkl

e-71-0o291-Isup2.hkl^{(241.3KB, hkl)}

Click here for additional data file.^{(6.8KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015006301/tk5363Isup3.cml

Click here for additional data file.^{(1.1MB, tif)}

. DOI: 10.1107/S2056989015006301/tk5363fig1.tif

Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.

Click here for additional data file.^{(1.6MB, tif)}

. DOI: 10.1107/S2056989015006301/tk5363fig2.tif

Crystal packing in the structure of the title compound, showing molecules linked by C—H⋯O hydrogen bonds (dashed lines).

CCDC reference: 1056731

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
C6H6O3B ⁱ	0.93	2.37	3.291(19)	170
C15H15BO2ⁱⁱ	0.97	2.34	3.278(3)	161
C18AH18AO2ⁱⁱⁱ	0.96	2.41	3.310(10)	156

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

Acknowledgments

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements, and the University Mohammed V, Rabat, Morocco, for financial support.

supplementary crystallographic information

S1. Comment

During recent years, pyridazinones have been a subject of numerous recent studies (Boukharsa et al., 2014) owing to their wide spectrum of pharmacological activities such as antimicrobial (Nagle et al., 2014), anti-fungal (El-Hashash et al., 2014), analgesic & anti-inflammatory (Tiryaki et al., 2013), anticancer (Csókás et al., 2013), anti-tubercular (Asif et al., 2014) and anti-hypertensive activities (Garkani-Nejad & Poshteh-Shirani, 2013). It has also been reported that pyridazinone derivative have remarkable insecticidal (Cao et al., 2003) and herbicidal activities (Jamet & Piedallu, 1975). In continuation of this line of research (Taoufik et al., 1984; Benchat et al., 1998; Abourichaa et al., 2003), we have developed a new pyridazin-3(2H)-one derivative. It will be subjected to further pharmacological investigations, especially tests of anticancer activity. Compound (I) is stable at room temperature, and its structure has been determined by NMR (¹H and ¹³ C). In this paper we wish to report the crystal structure determination of the title compound possessing the biologically active pyridazinone ring.

The molecule of the title compound is build up from 5-chlorobenzofuran-2-yl linked, via –CH₂– group, to six-membered heterocyclic ring which is related to acetate group as shown in Fig. 1. The benzofuran system is virtually planar with the largest deviation from the mean plane being -0.014 (2) Å at C4, and makes dihedral angle of 73.33 (8)° with the mean plane through the oxopyridazin (C10–C13,N1,N2) ring. Non classical C—H···O hydrogen bonds link the molecules into a three-dimensional network.

S2. Experimental

To a solution of 5-((5-chlorobenzofuran-2-yl)methyl)-6-methylpyridazin-3(2H)-one (0.5 g, 1.82 mmol) dissolved in tetrahydrofuran (15 ml) was added ethyl 2-bromoacetate (0.30 ml, 2.73 mmol), potassium carbonate (0.5 g, 3.64 mmol) and a catalytic amount of tetra-n-butylammonium bromide (0.05 g, 0.15 mmol). The mixture was stirred at room temperature for 6 h, and monitored by thin layer chromatography. The compound was removed by filtration and the filtrate concentrated under vacuum. The solid obtained was crystallized from ethanol to afford colourless crystals (Yield = 77%; M.pt = 136.9 °C).