5-(2,6-Dimethoxy­phen­oxy)-2-methyl­sulfanylmethyl-2H-tetra­zole

Nader Noroozi Pesyan; Negar Omidkhah; Mina Maghsoodi; Brian O Patrick

doi:10.1107/S1600536809006138

. 2009 Feb 28;65(Pt 3):o655. doi: 10.1107/S1600536809006138

5-(2,6-Dimethoxyphenoxy)-2-methylsulfanylmethyl-2H-tetrazole

Nader Noroozi Pesyan ^a,^*, Negar Omidkhah ^a, Mina Maghsoodi ^a, Brian O Patrick ^b

PMCID: PMC2968452 PMID: 21582303

Abstract

In the title molecule, C₁₁H₁₄N₄O₃S, the tetrazole and benzene rings are nearly perpendicular to each other, forming a dihedral angle of 104.93 (14)°. The crystal packing exhibits weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For a related crystal structure, see: Dabbagh et al. (2005 ▶).

Experimental

Crystal data

C₁₁H₁₄N₄O₃S
M _r = 282.32
Orthorhombic,
a = 12.1795 (5) Å
b = 11.0809 (4) Å
c = 9.9026 (4) Å
V = 1336.45 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 173 K
0.50 × 0.25 × 0.10 mm

Data collection

Bruker X8 APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.871, T _max = 0.975
7950 measured reflections
2873 independent reflections
2670 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.026
wR(F ²) = 0.067
S = 1.08
2873 reflections
175 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.15 e Å⁻³
Absolute structure: Flack (1983 ▶), 1220 Friedel pairs
Flack parameter: 0.06 (6)

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2008 ▶); program(s) used to solve structure: SIR (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809006138/cv2515sup1.cif

e-65-0o655-sup1.cif^{(17.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006138/cv2515Isup2.hkl

e-65-0o655-Isup2.hkl^{(138.2KB, 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
C10—H10B⋯O1ⁱ	0.99	2.45	3.4277 (19)	170
C11—H11C⋯O3ⁱ	0.98	2.45	3.421 (2)	172
C11—H11B⋯O1ⁱⁱ	0.98	2.52	3.471 (2)	163
C10—H10A⋯O2ⁱⁱⁱ	0.99	2.52	3.312 (2)	137

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

Acknowledgments

The authors thank the Urmia University Research Council for supporting this work. We also gratefully acknowledge the Structural Chemistry Facility of the University of British Columbia.

supplementary crystallographic information

Comment

In continuation of our structural study of tetrazole derivatives (Dabbagh et al., 2005) we report herein the structure of the title compound, (I).

In (I) (Fig. 1), the methylsulfanylmethylation proceeded at N2 atom on tetrazole ring. Because of the conjugation of O3 with tetrazole ring the bond distance O3—C9 [1.3388 (17) Å] is obviously shorter than O3—C1 [1.4062 (15) Å]. A similar effect has been found in 5-(4-nitrophenoxy)-1-methylsulfanylmethyl-1H-tetrazole (Dabbagh et al., 2005). Tetrazole ring in (I) is planar, and 2,6-dimethoxyphenoxy group deviates from the tetrazole ring plane so torsion angles C6—C1—O3—C9 and C1—O3—C9—N4 are -79.52 (17)° and -9.6 (2)°, respectively. The torsion angle O3—C1—C2—C3 of 174.02 (13)° implies steric interaction between the benzene and tetrazole rings. The S1—C10 bond [1.792 (2) Å] is slightly shorter than C11—S1 [1.798 (2) Å] in methylsulfanylmethyl group.

The crystal packing exhibits weak intermolecular C—H···O hydrogen bonds (Table 1).

Experimental

Dry DMSO, 5 ml, was added dropwise over a period of 30 min to a solution of 0.143 g of compound in 4 ml of acetic anhydride. The mixture was stirred for 40 h at 45–50°C, excess DMSO and acetic anhydride were removed under reduced pressure, and the residue was washed with several 2–3-ml portions of water. The precipitate was dissolved in 20 ml of methylene chloride, the solution was dried over calcium chloride and evaporated, and the residue was separated by column chromatography on silica gel to isolate compound. Yield 20%. IR spectrum (KBr), ν, cm^-1: 3050, 2975, 1590, 1530, 1390, 1370, 1300, 1260, 1180, 1110, 760. ¹H NMR (300 MHz, DMSO-d₆), δ: 7.14 (t, 1H, J = 10 Hz), 6.65 (d, 2H, J = 10 Hz), 5.48 (s, 2H), 3.71 (s, 6H), 2.17 (s, 3H). 13 C NMR (75 MHz, DMSO-d6), δ: 177.50, 152.29, 131.80, 126.74, 105.44, 78.88, 56.20, 56.03, 15.48. Mass spectrum (EI), m/z (Irel, %) 284 (0.6) [M + 2]⁺, 282 (15) [M]⁺, 281 (20), 236 (83), 151 (73), 140 (39), 107 (59), 43 (100).