7-Diethyl­amino-2-propyl­sulfan­yl-3-(1H-1,2,4-triazol-1-yl)-4H-thio­chromen-4-one

Chen Li; Guang Yan Yu; Xin Tian; Song Li; Tao Xiao

doi:10.1107/S1600536812015954

. 2012 Apr 18;68(Pt 5):o1435. doi: 10.1107/S1600536812015954

7-Diethylamino-2-propylsulfanyl-3-(1H-1,2,4-triazol-1-yl)-4H-thiochromen-4-one

Chen Li ^a, Guang Yan Yu ^a, Xin Tian ^a, Song Li ^a, Tao Xiao ^a,^*

PMCID: PMC3344555 PMID: 22590317

Abstract

In the title compound, C₁₈H₂₂N₄OS₂, the six-membered rings are almost coplanar, showing a dihedral angle between the mean planes of 9.0 (4)°, while the triazol ring is nearly perpendicular to the thiochromen-4-one unit, making an angle of 89.8 (4)°. In the crystal, C—H⋯N hydrogen bonds link the molecules in a stacked arrangement along the c axis.

Related literature

For related compounds, see: Nohara et al. (1977 ▶); Xiao et al. (2010 ▶); Liu et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₈H₂₂N₄OS₂
M _r = 374.52
Monoclinic,
a = 21.937 (4) Å
b = 9.817 (2) Å
c = 19.059 (4) Å
β = 109.85 (3)°
V = 3860.6 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.918, T _max = 0.944
3644 measured reflections
3549 independent reflections
2309 reflections with I > 2σ(I)
R _int = 0.062
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.062
wR(F ²) = 0.181
S = 1.00
3549 reflections
226 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009) ▶; software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812015954/zq2162sup1.cif

e-68-o1435-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015954/zq2162Isup2.hkl

e-68-o1435-Isup2.hkl^{(174.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812015954/zq2162Isup3.cml

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
C1—H1A⋯N4ⁱ	0.93	2.57	3.451 (5)	159

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

supplementary crystallographic information

Comment

The title compound is the key intermediate in the synthesis of a new kind of antiallergic drugs (Nohara et al., 1977). The crystal structure determination has been carried out in order to elucidate its molecular conformation (Fig. 1).

The molecular structure of the title compound, C₁₈H₂₂O₁N₄S₂, exhibits bond lengths and angles within normal ranges (Allen et al., 1987; Xiao et al., 2010; Liu et al., 2011). The six-membered rings A (C1—C6) and B (S1/C6—C9) are almost coplanar, showing a dihedral angle between the mean planes of 9.0 (4)°. The dihedral angle between the ring A (C1—C6) and C (N2/N3/N4/C17/C18) is 83.0 (4)° while the dihedral angle between the ring B (S1/C6—C9) and C (N2/N3/N4/C17—C18) is 89.8 (4)°.

In the crystal structure, intermolecular C—H···N hydrogen bonds (Table 2) link the molecules in a stacked arrangement along the c axis (Fig. 2).

Experimental

Diethylamine (13.8 ml, 134.4 mmol) was added to a solution of 2-(allylthio)-7-fluoro-3-(1H-1,2,4-triazol-1-yl)-4H-thiochromen-4-one (5 g, 15.7 mmol) in DMSO (30 ml) containing NaOH (1.8 g, 45 mmol). The yellow solution was stirred for about 12 h at room temperature. After completion of the reaction, the solution was poured into water (50 ml). The crystalline product was isolated by filtration and washed with water (300 ml). The precipitate was recrystallized with acetone and a yellow deposit was obtained (m.p. 420 K). Crystals suitable for X-ray analysis were obtained by dissolving the crude product (1.0 g) in ethanol (30 ml) and then allowing the solution to evaporate slowly at room temperature for about 7 d.