Diethyl [4-(1,3-benzothia­zol-2-yl)benz­yl]phospho­nate

Rong Peng; Huisheng Li

doi:10.1107/S1600536810047045

. 2010 Nov 20;66(Pt 12):o3236. doi: 10.1107/S1600536810047045

Diethyl [4-(1,3-benzothiazol-2-yl)benzyl]phosphonate

Rong Peng ^a,^*, Huisheng Li ^a

PMCID: PMC3011668 PMID: 21589525

Abstract

In the title molecule, C₁₈H₂₀NO₃PS, the benzene ring and the benzothiazole mean plane are almost coplanar, forming a dihedral angle of 2.29 (2)°. The two ethyl groups are each disordered over two conformations in ratios that refined to 0.59 (1):0.41 (1) and 0.56 (1):0.44 (1). In the crystal, weak intermolecular C—H⋯O hydrogen bonds link the molecules into layers parallel to the bc plane.

Related literature

For the cardiovascular activity of benzothiazole-substituted benzylphosphonate derivatives, see: Yoshino et al. (1986 ▶). For the crystal structure of a related benzothiazole-substituted derivative, see: Bhatia et al. (1991 ▶).

Experimental

Crystal data

C₁₈H₂₀NO₃PS
M _r = 361.38
Monoclinic,
a = 11.0441 (19) Å
b = 8.0927 (14) Å
c = 20.933 (4) Å
β = 94.943 (3)°
V = 1863.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.980, T _max = 0.986
11571 measured reflections
3641 independent reflections
2005 reflections with I > 2σ(I)
R _int = 0.104

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.150
S = 0.96
3641 reflections
259 parameters
8 restraints
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536810047045/cv2793sup1.cif

e-66-o3236-sup1.cif^{(21.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047045/cv2793Isup2.hkl

e-66-o3236-Isup2.hkl^{(178.5KB, 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
C5—H5⋯O1ⁱ	0.93	2.45	3.261 (5)	146
C13—H13⋯O1ⁱⁱ	0.93	2.53	3.310 (4)	141

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

Acknowledgments

The authors are grateful to Xiangfan University for financial support.

supplementary crystallographic information

Comment

It was found that benzothiazole-substituted benzylphosphonates derivatives could exhibit excellent cardiovascular activities (Yoshino et al., 1986). We herein report the structure of the diethyl 4-(benzo[d]thiazol-2-yl)benzylphosphonate (I) (Fig. 1).

In (I), the bond lengths and angles are normal and comparable with those observed in the related compound (Bhatia et al., 1991). The benzene ring and the benzothiazole mean plane are almost coplanar forming a dihedral angle of 2.29 (2)°. Weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into layers parallel to bc plane.

Experimental

The title compound was synthesized according to the method of Yoshino et al. (1986). Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of the solution in hexane-MeOH (3:1).