Crystal structure of 4-chloro-2-[(5-eth­oxy-1,3,4-thia­diazol-2-yl)meth­yl]-5-(piperidin-1-yl)pyridazin-3(2H)-one

Hongsen Li; Xinfeng Ren; Ya Li; Linjing Zhao

doi:10.1107/S1600536814020662

. 2014 Sep 20;70(Pt 10):o1113. doi: 10.1107/S1600536814020662

Crystal structure of 4-chloro-2-[(5-ethoxy-1,3,4-thiadiazol-2-yl)methyl]-5-(piperidin-1-yl)pyridazin-3(2H)-one

Hongsen Li ^a,^*, Xinfeng Ren ^a, Ya Li ^a, Linjing Zhao ^a

PMCID: PMC4257213 PMID: 25484702

Abstract

In the title molecule, C₁₄H₁₈ClN₅O₂S, the six atoms of the 1,6-dihydropyridazine ring are essentially coplanar (r.m.s. deviation = 0.008 Å), and the dihedral angle between this and the 1,3,4-thiadiazole ring is 62.06 (10)°. In the crystal, centrosymmetrically related molecules are linked by intermolecular C—H—O hydrogen bonding to form a supramolecular dimer. The terminal ethyl group is statistically disordered over two positions.

Keywords: pyridazinone derivatives, crystal structure, C—H—O hydrogen bonding

Related literature

For the biological activity of pyridazinone derivatives, see: Abouzid et al. (2008 ▶); Siddiqui et al. (2010 ▶), and for their synthesis, see: Wang et al. (2010 ▶); Zhang et al. (2002 ▶). graphic file with name e-70-o1113-scheme1.jpg

Experimental

Crystal data

C₁₄H₁₈ClN₅O₂S
M _r = 355.84
Triclinic,
a = 5.2840 (8) Å
b = 11.0323 (16) Å
c = 14.902 (2) Å
α = 107.318 (2)°
β = 91.590 (2)°
γ = 99.528 (2)°
V = 815.1 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 296 K
0.30 × 0.24 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.895, T _max = 0.942
4244 measured reflections
2828 independent reflections
2490 reflections with I > 2σ(I)
R _int = 0.012

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.121
S = 1.58
2828 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814020662/tk5340sup1.cif

e-70-o1113-sup1.cif^{(21.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814020662/tk5340Isup2.hkl

e-70-o1113-Isup2.hkl^{(138.8KB, hkl)}

Click here for additional data file.^{(6.6KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814020662/tk5340Isup3.cml

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

. DOI: 10.1107/S1600536814020662/tk5340fig1.tif

Molecular structure of the title compound showing atom labelling and displacement ellipsoids at 50%.

CCDC reference: 1024313

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14A—H14A⋯O1ⁱ	0.96	2.45	3.366 (11)	160

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Symmetry code: (i) Inline graphic .

Acknowledgments

Financial support from the Development Program of the Shanghai University of Engineering Science is gratefully acknowledged.

supplementary crystallographic information

S1. Introduction

S2. Experimental

A mixture of 4,5-dichloro-2-[(5-ethoxy-1,3,4-thiadiazol-2-yl)methyl]-pyridazin-3(2H)-one (3.98 g, 1.3 mmol), piperidine (1.37 g, 19.5 mmol), potassium carbonate (3 g) and dry DMF (30mL) was stirred at 40^oC for 8 h. The mixture was then poured into ice-water and a yellow precipitate -formed. The precipitate was washed with water, followed by vaccum drying, to give the pure title compound (3.38 g, yield: 73.2 %). The obtained compound was recrystallized from its ethyl acetate/petroleum ether (5:1) to give yellow crystals.

S2.1. Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H = 0.93 to 0.97 Å) and were included in the refinement in the riding model approximation, with U_iso(H) = 1.2–1.5U_eq(C). The terminal ethyl group (C13 and C14) was statistically disordered over two positions.