2-(Biphenyl-4-yl)-5-[3-(4,5,6,7-tetra­hydro­thieno[3,2-c]pyridine-5-ylsulfon­yl)thio­phen-2-yl]-1,3,4-oxa­diazole

Hoong-Kun Fun; Madhukar Hemamalini; Sankappa Rai; A M Isloor; Prakash Shetty

doi:10.1107/S1600536811038621

. 2011 Sep 30;67(Pt 10):o2781–o2782. doi: 10.1107/S1600536811038621

2-(Biphenyl-4-yl)-5-[3-(4,5,6,7-tetrahydrothieno[3,2-c]pyridine-5-ylsulfonyl)thiophen-2-yl]-1,3,4-oxadiazole

Hoong-Kun Fun ^a,^*,^‡, Madhukar Hemamalini ^a, Sankappa Rai ^b, A M Isloor ^c, Prakash Shetty ^d

PMCID: PMC3201303 PMID: 22058820

Abstract

In the title molecule, C₂₅H₁₉N₃O₃S₃, the tetrahydropyridine ring adopts a half-chair conformation. The dihedral angle between the least-squares plane through the tetrahydropyridine ring and two thiophene and two benzene rings are 6.25 (9), 89.49 (9), 76.43 (9) and 84.93 (8)°, respectively, while the dihedral angle between the 1,3,4-oxadiazole and tetrahydropyridine rings is 81.14 (9)°. In the crystal, adjacent molecules are connected via weak C—H⋯N hydrogen bonds, forming a chain along the b axis.

Related literature

For applications of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine derivatives, see: Lopez-Rodriguez et al. (2001 ▶); Roth et al. (1994 ▶); Ying & Rusak (1997 ▶). For a related structure, see: Fun et al. (2011 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₅H₁₉N₃O₃S₃
M _r = 505.61
Triclinic,
a = 7.9108 (1) Å
b = 12.0943 (1) Å
c = 12.9498 (2) Å
α = 69.253 (1)°
β = 76.794 (1)°
γ = 77.460 (1)°
V = 1115.30 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 100 K
0.33 × 0.16 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.889, T _max = 0.966
33050 measured reflections
8887 independent reflections
5904 reflections with I > 2σ(I)
R _int = 0.058

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.122
S = 1.03
8887 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811038621/tk2792sup1.cif

e-67-o2781-sup1.cif^{(24KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038621/tk2792Isup2.hkl

e-67-o2781-Isup2.hkl^{(425.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811038621/tk2792Isup3.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
C24—H24A⋯N1ⁱ	0.99	2.52	3.417 (2)	150

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Symmetry code: (i) Inline graphic .

Acknowledgments

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship. AMI thanks the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for the Young Scientist award.

supplementary crystallographic information

Comment

4,5,6,7-Tetrahydrothieno[3,2-c]pyridine derivatives have been extensively studied in medicinal chemistry due to their various biological activities (Lopez-Rodriguez et al., 2001). 4,5,6,7-Tetrahydrothieno[3,2-c] pyridine oxadiazole derivatives are mainly used in CNS functions and disorders such as schizophrenia (Roth et al., 1994), depression, epilepsy, migraine, and control of circadian rhythm (Ying & Rusak, 1997). Keeping in view of the biological importance of this class of compound, we synthesized the title compound to study its X-ray crystal structure.

In the title compound (Fig. 1), the rings A (N3/C19,C20,C23–C25), B (N1/N2/O1/C13,C14), C (S3/C20–C23), D (S2/C15–C18) E (C7–C12) and F (C1–C6) are essentially planar. The tetrahydropyridine (N3/C19,C20, C23–C25) ring adopts a half-chair conformation with puckering parameters Q = 0.4970 (18) Å, θ = 129.3 (2)° and φ = 153.0 (3)° . The dihedral angle between the least-square planes of the rings are A/B = 81.14 (9)°, A/C = 6.25 (9)°, A/D = 89.49 (9)°, A/E = 84.93 (8)°, A/F = 76.43 (9)° B/C = 78.71 (10)°, B/D = 9.55 (10)°, B/E = 10.88 (9)°, B/F = 11.16 (10)°, C/D = 87.86 (9)°, C/E = 83.55 (9)°, C/F = 73.04 (9)°, D/E = 13.31 (9)° and D/F = 16.40 (9)°.

In the crystal structure, (Fig. 2), adjacent molecules are connected via weak intermolecular C—H···N (Table 1) hydrogen bonds to form one-dimensional chains along the b-axis.

Experimental

To a mixture of 3-(6,7-dihydrothieno[3,2-c]pyridine-5(4H)-ylsulfonyl) thiophene-2-carbohydrazide (0.5 g, 0.0014 mol) and biphenyl carboxylic acid (0.28 g, 0.0014 mol), neutral alumina (0.5 g) and POCl₃ (1.1 g, 0.007 mol) were added. The resulting mixture was irradiated in a microwave oven for 5 min. Mass analysis of crude reaction mixture confirmed the completion of the reaction. The reaction mixture was concentrated and the residue was purified by column chromatography to get the title compound, which was recrystallised using acetone. Yield: 68%, m.p. 441–443 K.