6-Methyl-N-(4-methoxy­phen­yl)-2-[(E)-(4-methyl­phen­yl)methyl­eneamino]-4,5,6,7-tetra­hydro­thieno[2,3-c]pyridine-3-carboxamide

G N Anilkumar; M K Kokila; Puttaraja; S Mohan; J Saravanan

doi:10.1107/S1600536808017236

. 2008 Jun 13;64(Pt 7):o1258. doi: 10.1107/S1600536808017236

6-Methyl-N-(4-methoxyphenyl)-2-[(E)-(4-methylphenyl)methyleneamino]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide

G N Anilkumar ^a, M K Kokila ^b,^*, Puttaraja ^b, S Mohan ^c, J Saravanan ^c

PMCID: PMC2961643 PMID: 21202892

Abstract

The molecular structure of the title compound, C₂₄H₂₅N₃O₂S, is stabilized by intramolecular N—H⋯N, C—H⋯O and C—H⋯S hydrogen bonds. There are no significant intermolecular interactions.

Related literature

For related literature, see: Gewald et al. (1966 ▶); Cohen et al. (1977 ▶); Csaszar & Morvay (1983 ▶); Lakshmi et al. (1985 ▶); Mohan & Saravanan (2003 ▶); Dzhurayev et al. (1992 ▶); Sebnis et al. (1999 ▶); Anilkumar et al. (2005 ▶); El-Maghraby, Haroun & Mohamed (1984 ▶).

Experimental

Crystal data

C₂₄H₂₅N₃O₂S
M _r = 419.53
Triclinic,
a = 8.3905 (11) Å
b = 9.9883 (13) Å
c = 12.9549 (17) Å
α = 91.375 (2)°
β = 94.789 (3)°
γ = 96.121 (2)°
V = 1075.2 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 292 (2) K
0.32 × 0.28 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.942, T _max = 0.967
10653 measured reflections
3967 independent reflections
2633 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.085
wR(F ²) = 0.183
S = 1.14
3967 reflections
274 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 1998 ▶); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017236/hg2409sup1.cif

e-64-o1258-sup1.cif^{(22.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017236/hg2409Isup2.hkl

e-64-o1258-Isup2.hkl^{(191KB, 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
N2—H2⋯N1	0.86	2.12	2.807 (4)	137
C1—H1⋯S1	0.93	2.60	3.051 (4)	110
C16—H16⋯O1	0.93	2.27	2.863 (5)	121

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Acknowledgments

The authors are grateful to Professor T. N. Guru Row, Indian Institute of Science and Department of Science and Technology, India, for the data collection on the CCD facility and to Bangalore University. GNA thanks MSRIT for encouragement and support.

supplementary crystallographic information

Comment

The title compound (I) was one amongst bicyclic tetrahydropyridinothiophenes (Sebnis et al., 1999), found to exhibit antimicrobial and anti-inflammatory activities. Schiff bases (Csaszar & Morvay, 1983; Lakshmi et al., 1985; Cohen et al., 1977) and their thiophene derivatives (El-Maghraby et al., 1984; Dzhurayev et al., 1992; Gewald et al., 1966) were known for their wide range of biological activities such as antibacterial, antifungal and antitubercular activities. Sulfur containing Schiff bases are particularly effective.(Mohan & Saravanan, 2003).

The bicyclic system exhibits non-planarity, the N—CH₃ group shows a significant deviation from the molecular plane. The p-methoxyphenyl ring (C11–C16/O2/C23) and 4- methylphenyl ring (C17–C22/C24) make dihedral angles of 7.7 (2) and 10.2 (3)°, respectively, with thiophene ring. The torsion angles C3—C9—N2—C11 and C2—N1—C1—C17 show the anti conformation of the two units about the C9—N2 and N1—C1 bonds. In (I) (Fig. 1), intramolecular N2—H2···N1 and C16—H16···O1 hydrogen bonds form pseudo-six-membered rings, while the intramolecular C1—H1···S1 hydrogen bond forms a pseudo-fivemembered ring, thus locking the molecular conformation and eliminating conformational flexibility. (Anilkumar et al. 2005). Molecules are arranged in zigzag layers viewed along a axis.(Fig 2).

Experimental

The title compound, (I), was synthesized using the Gewald reaction (Gewald et al., 1966). 4-Methoxyphenyl 2-cyanoacetamide (0.04 mol) was refluxed with N-methylpiperidin-4-one (0.04 mol) in the presence of ammonium acetate (1.00 g) and glacial acetic acid (2 ml) in benzene.This mixture was treated with sulfur (1.28 g, 0.04 mol), dimethylamine (4 ml) and ethanol at 323 K. The product was treated with 4- methyl benzaldehyde in an equimolar ratio in the presence of 2- propanol and a catalytic amount of glacial acetic acid under microwave irradiation, which yielded (I). This was purified and crystallized from N,N-dimethylformamide and ethanol (1:2) by slow evaporation.