organic compounds
6-Methyl-N-(4-methoxyphenyl)-2-[(E)-(4-methylphenyl)methyleneamino]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide
aDepartment of Physics, MS Ramaiah Institute of Technology, MSRIT Post, Bangalore 560 054, Karnataka, India, bDepartment of Physics, Bangalore University, Bangalore 560 056, Karnataka, India, and cPES College of Pharmacy, Hanumanthanagar, Bangalore 560 050, Karnataka, India
*Correspondence e-mail: prmkkgroup@gmail.com
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
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Refinement
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Data collection: SMART (Bruker, 1998); cell 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).
Supporting information
10.1107/S1600536808017236/hg2409sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808017236/hg2409Isup2.hkl
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.
H atoms were positioned geometrically, with N—H = 0.86 and C— H = 0.93, 0.97 and 0.96 A° for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,N), where x =1.5 for methyl H and x = 1.2 for all other H atoms. A rotating group model was used for methyl groups.
Data collection: SMART (Bruker, 1998); cell
SMART (Bruker, 1998); 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).C24H25N3O2S | Z = 2 |
Mr = 419.53 | F(000) = 444 |
Triclinic, P1 | Dx = 1.296 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.3905 (11) Å | Cell parameters from 380 reflections |
b = 9.9883 (13) Å | θ = 1.6–28.6° |
c = 12.9549 (17) Å | µ = 0.18 mm−1 |
α = 91.375 (2)° | T = 292 K |
β = 94.789 (3)° | Block, yellow |
γ = 96.121 (2)° | 0.32 × 0.28 × 0.22 mm |
V = 1075.2 (2) Å3 |
Bruker SMART CCD area-detector diffractometer | 3967 independent reflections |
Radiation source: fine-focus sealed tube | 2633 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
ψ and ω scans | θmax = 25.5°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.942, Tmax = 0.967 | k = −12→12 |
10653 measured reflections | l = −15→15 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.085 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.184 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0919P)2 + 0.1278P] where P = (Fo2 + 2Fc2)/3 |
3967 reflections | (Δ/σ)max = 0.001 |
274 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C24H25N3O2S | γ = 96.121 (2)° |
Mr = 419.53 | V = 1075.2 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.3905 (11) Å | Mo Kα radiation |
b = 9.9883 (13) Å | µ = 0.18 mm−1 |
c = 12.9549 (17) Å | T = 292 K |
α = 91.375 (2)° | 0.32 × 0.28 × 0.22 mm |
β = 94.789 (3)° |
Bruker SMART CCD area-detector diffractometer | 3967 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2633 reflections with I > 2σ(I) |
Tmin = 0.942, Tmax = 0.967 | Rint = 0.051 |
10653 measured reflections |
R[F2 > 2σ(F2)] = 0.085 | 0 restraints |
wR(F2) = 0.184 | H-atom parameters constrained |
S = 1.14 | Δρmax = 0.26 e Å−3 |
3967 reflections | Δρmin = −0.24 e Å−3 |
274 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.15650 (12) | 0.11892 (10) | 0.10349 (7) | 0.0563 (3) | |
O1 | 0.5787 (3) | 0.2412 (3) | 0.3856 (2) | 0.0713 (9) | |
O2 | 0.9097 (3) | 0.8527 (2) | 0.5084 (2) | 0.0604 (7) | |
N1 | 0.3079 (3) | 0.3800 (3) | 0.1240 (2) | 0.0471 (7) | |
N2 | 0.5036 (4) | 0.4298 (3) | 0.3103 (2) | 0.0523 (8) | |
H2 | 0.4367 | 0.4575 | 0.2637 | 0.063* | |
N3 | 0.2336 (4) | −0.2086 (3) | 0.2703 (2) | 0.0522 (8) | |
C1 | 0.2503 (5) | 0.4032 (4) | 0.0322 (3) | 0.0551 (10) | |
H1 | 0.1949 | 0.3317 | −0.0078 | 0.066* | |
C2 | 0.2865 (4) | 0.2518 (3) | 0.1637 (3) | 0.0442 (9) | |
C3 | 0.3661 (4) | 0.2116 (3) | 0.2540 (3) | 0.0433 (9) | |
C4 | 0.3748 (5) | −0.0062 (4) | 0.3650 (3) | 0.0516 (10) | |
H4A | 0.4844 | −0.0254 | 0.3582 | 0.062* | |
H4B | 0.3741 | 0.0474 | 0.4283 | 0.062* | |
C5 | 0.2676 (5) | −0.1373 (4) | 0.3715 (3) | 0.0568 (10) | |
H5A | 0.3195 | −0.1948 | 0.4200 | 0.068* | |
H5B | 0.1670 | −0.1185 | 0.3976 | 0.068* | |
C6 | 0.1331 (5) | −0.1315 (4) | 0.2017 (3) | 0.0556 (10) | |
H6A | 0.0266 | −0.1339 | 0.2259 | 0.067* | |
H6B | 0.1224 | −0.1715 | 0.1321 | 0.067* | |
C7 | 0.2076 (4) | 0.0119 (4) | 0.1999 (3) | 0.0469 (9) | |
C8 | 0.3183 (4) | 0.0725 (3) | 0.2738 (3) | 0.0415 (8) | |
C9 | 0.4911 (4) | 0.2950 (4) | 0.3227 (3) | 0.0479 (9) | |
C10 | 0.1536 (5) | −0.3431 (4) | 0.2811 (3) | 0.0664 (12) | |
H10A | 0.0545 | −0.3371 | 0.3121 | 0.100* | |
H10B | 0.2219 | −0.3938 | 0.3244 | 0.100* | |
H10C | 0.1315 | −0.3874 | 0.2141 | 0.100* | |
C11 | 0.6118 (4) | 0.5304 (3) | 0.3637 (3) | 0.0460 (9) | |
C12 | 0.6143 (5) | 0.6609 (4) | 0.3305 (3) | 0.0596 (11) | |
H12 | 0.5460 | 0.6787 | 0.2734 | 0.072* | |
C13 | 0.7141 (5) | 0.7643 (4) | 0.3789 (3) | 0.0603 (11) | |
H13 | 0.7138 | 0.8508 | 0.3538 | 0.072* | |
C14 | 0.8163 (4) | 0.7420 (4) | 0.4655 (3) | 0.0466 (9) | |
C15 | 0.8154 (5) | 0.6133 (4) | 0.4991 (3) | 0.0573 (10) | |
H15 | 0.8838 | 0.5961 | 0.5563 | 0.069* | |
C16 | 0.7151 (5) | 0.5082 (4) | 0.4498 (3) | 0.0591 (11) | |
H16 | 0.7166 | 0.4216 | 0.4745 | 0.071* | |
C17 | 0.2670 (4) | 0.5351 (4) | −0.0126 (3) | 0.0493 (9) | |
C18 | 0.1988 (6) | 0.5521 (4) | −0.1128 (3) | 0.0772 (14) | |
H18 | 0.1445 | 0.4782 | −0.1505 | 0.093* | |
C19 | 0.2106 (6) | 0.6756 (5) | −0.1563 (3) | 0.0775 (14) | |
H19 | 0.1640 | 0.6838 | −0.2233 | 0.093* | |
C20 | 0.2889 (4) | 0.7875 (4) | −0.1044 (3) | 0.0535 (10) | |
C21 | 0.3603 (5) | 0.7708 (4) | −0.0057 (3) | 0.0634 (11) | |
H21 | 0.4165 | 0.8445 | 0.0312 | 0.076* | |
C22 | 0.3487 (5) | 0.6468 (4) | 0.0379 (3) | 0.0625 (11) | |
H22 | 0.3982 | 0.6384 | 0.1040 | 0.075* | |
C23 | 1.0176 (5) | 0.8341 (4) | 0.5968 (3) | 0.0619 (11) | |
H23A | 0.9580 | 0.7953 | 0.6508 | 0.093* | |
H23B | 1.0731 | 0.9197 | 0.6208 | 0.093* | |
H23C | 1.0944 | 0.7750 | 0.5781 | 0.093* | |
C24 | 0.2999 (5) | 0.9248 (4) | −0.1523 (3) | 0.0717 (12) | |
H24A | 0.2827 | 0.9139 | −0.2264 | 0.108* | |
H24B | 0.4045 | 0.9718 | −0.1337 | 0.108* | |
H24C | 0.2193 | 0.9756 | −0.1273 | 0.108* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0607 (7) | 0.0545 (6) | 0.0497 (6) | 0.0002 (5) | −0.0136 (5) | 0.0075 (5) |
O1 | 0.0739 (19) | 0.0560 (17) | 0.0772 (19) | 0.0045 (14) | −0.0340 (16) | 0.0122 (14) |
O2 | 0.0565 (17) | 0.0483 (16) | 0.0715 (18) | −0.0001 (13) | −0.0165 (14) | 0.0049 (13) |
N1 | 0.0499 (18) | 0.0470 (18) | 0.0431 (17) | 0.0026 (14) | −0.0026 (14) | 0.0093 (14) |
N2 | 0.057 (2) | 0.0468 (19) | 0.0492 (18) | 0.0056 (15) | −0.0159 (15) | 0.0039 (14) |
N3 | 0.056 (2) | 0.0458 (18) | 0.0542 (19) | 0.0054 (15) | −0.0008 (15) | 0.0083 (15) |
C1 | 0.063 (3) | 0.053 (2) | 0.045 (2) | 0.0000 (19) | −0.0124 (19) | 0.0076 (18) |
C2 | 0.045 (2) | 0.047 (2) | 0.040 (2) | 0.0038 (17) | −0.0019 (16) | 0.0018 (16) |
C3 | 0.040 (2) | 0.049 (2) | 0.041 (2) | 0.0107 (17) | −0.0005 (16) | 0.0045 (16) |
C4 | 0.058 (2) | 0.054 (2) | 0.044 (2) | 0.0104 (19) | 0.0002 (18) | 0.0074 (17) |
C5 | 0.071 (3) | 0.051 (2) | 0.048 (2) | 0.006 (2) | 0.005 (2) | 0.0053 (18) |
C6 | 0.053 (2) | 0.053 (2) | 0.059 (2) | 0.0027 (19) | −0.0004 (19) | 0.0033 (19) |
C7 | 0.047 (2) | 0.052 (2) | 0.044 (2) | 0.0109 (18) | 0.0027 (17) | 0.0064 (17) |
C8 | 0.041 (2) | 0.044 (2) | 0.0399 (19) | 0.0080 (16) | 0.0003 (16) | 0.0031 (15) |
C9 | 0.049 (2) | 0.049 (2) | 0.044 (2) | 0.0047 (18) | −0.0066 (17) | 0.0058 (17) |
C10 | 0.073 (3) | 0.052 (3) | 0.073 (3) | −0.001 (2) | 0.004 (2) | 0.007 (2) |
C11 | 0.047 (2) | 0.043 (2) | 0.047 (2) | 0.0043 (17) | −0.0055 (17) | 0.0004 (17) |
C12 | 0.062 (3) | 0.050 (2) | 0.062 (2) | 0.004 (2) | −0.023 (2) | 0.0092 (19) |
C13 | 0.060 (3) | 0.044 (2) | 0.074 (3) | 0.0064 (19) | −0.015 (2) | 0.017 (2) |
C14 | 0.046 (2) | 0.041 (2) | 0.052 (2) | 0.0048 (17) | 0.0009 (18) | 0.0040 (17) |
C15 | 0.068 (3) | 0.049 (2) | 0.051 (2) | 0.003 (2) | −0.018 (2) | 0.0069 (18) |
C16 | 0.074 (3) | 0.047 (2) | 0.053 (2) | 0.005 (2) | −0.018 (2) | 0.0157 (18) |
C17 | 0.050 (2) | 0.056 (2) | 0.040 (2) | 0.0031 (19) | −0.0073 (17) | 0.0060 (18) |
C18 | 0.104 (4) | 0.064 (3) | 0.053 (3) | −0.011 (3) | −0.030 (2) | 0.012 (2) |
C19 | 0.096 (4) | 0.073 (3) | 0.056 (3) | −0.002 (3) | −0.028 (2) | 0.016 (2) |
C20 | 0.049 (2) | 0.061 (3) | 0.053 (2) | 0.012 (2) | 0.0074 (19) | 0.014 (2) |
C21 | 0.071 (3) | 0.055 (3) | 0.059 (3) | −0.008 (2) | −0.006 (2) | 0.002 (2) |
C22 | 0.074 (3) | 0.067 (3) | 0.043 (2) | 0.002 (2) | −0.011 (2) | 0.012 (2) |
C23 | 0.060 (3) | 0.066 (3) | 0.054 (2) | 0.001 (2) | −0.015 (2) | −0.001 (2) |
C24 | 0.076 (3) | 0.068 (3) | 0.072 (3) | 0.010 (2) | 0.009 (2) | 0.018 (2) |
S1—C7 | 1.721 (3) | C10—H10B | 0.9600 |
S1—C2 | 1.749 (4) | C10—H10C | 0.9600 |
O1—C9 | 1.225 (4) | C11—C12 | 1.380 (5) |
O2—C14 | 1.363 (4) | C11—C16 | 1.392 (5) |
O2—C23 | 1.427 (4) | C12—C13 | 1.363 (5) |
N1—C1 | 1.282 (4) | C12—H12 | 0.9300 |
N1—C2 | 1.391 (4) | C13—C14 | 1.391 (5) |
N2—C9 | 1.354 (4) | C13—H13 | 0.9300 |
N2—C11 | 1.407 (4) | C14—C15 | 1.366 (5) |
N2—H2 | 0.8600 | C15—C16 | 1.381 (5) |
N3—C10 | 1.452 (4) | C15—H15 | 0.9300 |
N3—C6 | 1.463 (4) | C16—H16 | 0.9300 |
N3—C5 | 1.469 (5) | C17—C22 | 1.367 (5) |
C1—C17 | 1.450 (5) | C17—C18 | 1.397 (5) |
C1—H1 | 0.9300 | C18—C19 | 1.366 (5) |
C2—C3 | 1.387 (4) | C18—H18 | 0.9300 |
C3—C8 | 1.440 (5) | C19—C20 | 1.366 (6) |
C3—C9 | 1.485 (5) | C19—H19 | 0.9300 |
C4—C5 | 1.516 (5) | C20—C21 | 1.387 (5) |
C4—C8 | 1.506 (4) | C20—C24 | 1.516 (5) |
C4—H4A | 0.9700 | C21—C22 | 1.371 (5) |
C4—H4B | 0.9700 | C21—H21 | 0.9300 |
C5—H5A | 0.9700 | C22—H22 | 0.9300 |
C5—H5B | 0.9700 | C23—H23A | 0.9600 |
C6—C7 | 1.502 (5) | C23—H23B | 0.9600 |
C6—H6A | 0.9700 | C23—H23C | 0.9600 |
C6—H6B | 0.9700 | C24—H24A | 0.9600 |
C7—C8 | 1.360 (5) | C24—H24B | 0.9600 |
C10—H10A | 0.9600 | C24—H24C | 0.9600 |
C7—S1—C2 | 91.41 (17) | H10B—C10—H10C | 109.5 |
C14—O2—C23 | 117.7 (3) | C12—C11—C16 | 117.2 (3) |
C1—N1—C2 | 121.1 (3) | C12—C11—N2 | 118.4 (3) |
C9—N2—C11 | 128.4 (3) | C16—C11—N2 | 124.4 (3) |
C9—N2—H2 | 115.8 | C13—C12—C11 | 121.9 (3) |
C11—N2—H2 | 115.8 | C13—C12—H12 | 119.0 |
C10—N3—C6 | 110.1 (3) | C11—C12—H12 | 119.0 |
C10—N3—C5 | 110.9 (3) | C12—C13—C14 | 120.7 (3) |
C6—N3—C5 | 109.3 (3) | C12—C13—H13 | 119.6 |
N1—C1—C17 | 123.4 (3) | C14—C13—H13 | 119.6 |
N1—C1—H1 | 118.3 | O2—C14—C15 | 126.2 (3) |
C17—C1—H1 | 118.3 | O2—C14—C13 | 115.9 (3) |
C3—C2—N1 | 125.1 (3) | C15—C14—C13 | 117.9 (3) |
C3—C2—S1 | 111.3 (3) | C14—C15—C16 | 121.4 (3) |
N1—C2—S1 | 123.6 (2) | C14—C15—H15 | 119.3 |
C2—C3—C8 | 111.7 (3) | C16—C15—H15 | 119.3 |
C2—C3—C9 | 126.5 (3) | C15—C16—C11 | 120.7 (3) |
C8—C3—C9 | 121.8 (3) | C15—C16—H16 | 119.6 |
C5—C4—C8 | 111.0 (3) | C11—C16—H16 | 119.6 |
C5—C4—H4A | 109.4 | C22—C17—C18 | 116.7 (3) |
C8—C4—H4A | 109.4 | C22—C17—C1 | 123.5 (3) |
C5—C4—H4B | 109.4 | C18—C17—C1 | 119.7 (3) |
C8—C4—H4B | 109.4 | C19—C18—C17 | 121.0 (4) |
H4A—C4—H4B | 108.0 | C19—C18—H18 | 119.5 |
N3—C5—C4 | 112.0 (3) | C17—C18—H18 | 119.5 |
N3—C5—H5A | 109.2 | C18—C19—C20 | 121.9 (4) |
C4—C5—H5A | 109.2 | C18—C19—H19 | 119.0 |
N3—C5—H5B | 109.2 | C20—C19—H19 | 119.0 |
C4—C5—H5B | 109.2 | C19—C20—C21 | 117.4 (4) |
H5A—C5—H5B | 107.9 | C19—C20—C24 | 121.8 (4) |
N3—C6—C7 | 109.9 (3) | C21—C20—C24 | 120.8 (4) |
N3—C6—H6A | 109.7 | C22—C21—C20 | 120.7 (4) |
C7—C6—H6A | 109.7 | C22—C21—H21 | 119.7 |
N3—C6—H6B | 109.7 | C20—C21—H21 | 119.7 |
C7—C6—H6B | 109.7 | C21—C22—C17 | 122.2 (3) |
H6A—C6—H6B | 108.2 | C21—C22—H22 | 118.9 |
C8—C7—C6 | 124.7 (3) | C17—C22—H22 | 118.9 |
C8—C7—S1 | 112.6 (3) | O2—C23—H23A | 109.5 |
C6—C7—S1 | 122.6 (3) | O2—C23—H23B | 109.5 |
C7—C8—C3 | 113.0 (3) | H23A—C23—H23B | 109.5 |
C7—C8—C4 | 119.7 (3) | O2—C23—H23C | 109.5 |
C3—C8—C4 | 127.4 (3) | H23A—C23—H23C | 109.5 |
O1—C9—N2 | 123.0 (3) | H23B—C23—H23C | 109.5 |
O1—C9—C3 | 120.2 (3) | C20—C24—H24A | 109.5 |
N2—C9—C3 | 116.9 (3) | C20—C24—H24B | 109.5 |
N3—C10—H10A | 109.5 | H24A—C24—H24B | 109.5 |
N3—C10—H10B | 109.5 | C20—C24—H24C | 109.5 |
H10A—C10—H10B | 109.5 | H24A—C24—H24C | 109.5 |
N3—C10—H10C | 109.5 | H24B—C24—H24C | 109.5 |
H10A—C10—H10C | 109.5 | ||
C2—N1—C1—C17 | 179.1 (3) | C2—C3—C9—O1 | −162.9 (4) |
C1—N1—C2—C3 | 168.5 (4) | C8—C3—C9—O1 | 14.4 (5) |
C1—N1—C2—S1 | −10.3 (5) | C2—C3—C9—N2 | 16.0 (5) |
C7—S1—C2—C3 | 0.7 (3) | C8—C3—C9—N2 | −166.7 (3) |
C7—S1—C2—N1 | 179.6 (3) | C9—N2—C11—C12 | 173.1 (4) |
N1—C2—C3—C8 | −179.6 (3) | C9—N2—C11—C16 | −8.3 (6) |
S1—C2—C3—C8 | −0.7 (4) | C16—C11—C12—C13 | 0.4 (6) |
N1—C2—C3—C9 | −2.1 (6) | N2—C11—C12—C13 | 179.1 (4) |
S1—C2—C3—C9 | 176.8 (3) | C11—C12—C13—C14 | −1.0 (7) |
C10—N3—C5—C4 | 170.6 (3) | C23—O2—C14—C15 | 0.0 (5) |
C6—N3—C5—C4 | −67.8 (4) | C23—O2—C14—C13 | −179.4 (3) |
C8—C4—C5—N3 | 45.9 (4) | C12—C13—C14—O2 | −179.4 (4) |
C10—N3—C6—C7 | 173.8 (3) | C12—C13—C14—C15 | 1.1 (6) |
C5—N3—C6—C7 | 51.6 (4) | O2—C14—C15—C16 | 179.8 (4) |
N3—C6—C7—C8 | −20.0 (5) | C13—C14—C15—C16 | −0.8 (6) |
N3—C6—C7—S1 | 161.5 (3) | C14—C15—C16—C11 | 0.3 (7) |
C2—S1—C7—C8 | −0.5 (3) | C12—C11—C16—C15 | −0.1 (6) |
C2—S1—C7—C6 | 178.1 (3) | N2—C11—C16—C15 | −178.7 (4) |
C6—C7—C8—C3 | −178.4 (3) | N1—C1—C17—C22 | 1.5 (6) |
S1—C7—C8—C3 | 0.1 (4) | N1—C1—C17—C18 | −179.2 (4) |
C6—C7—C8—C4 | 0.5 (5) | C22—C17—C18—C19 | −1.6 (7) |
S1—C7—C8—C4 | 179.1 (3) | C1—C17—C18—C19 | 179.0 (4) |
C2—C3—C8—C7 | 0.4 (4) | C17—C18—C19—C20 | 0.0 (8) |
C9—C3—C8—C7 | −177.3 (3) | C18—C19—C20—C21 | 1.5 (7) |
C2—C3—C8—C4 | −178.4 (3) | C18—C19—C20—C24 | −179.1 (4) |
C9—C3—C8—C4 | 3.9 (6) | C19—C20—C21—C22 | −1.4 (6) |
C5—C4—C8—C7 | −12.8 (5) | C24—C20—C21—C22 | 179.3 (4) |
C5—C4—C8—C3 | 165.9 (3) | C20—C21—C22—C17 | −0.3 (7) |
C11—N2—C9—O1 | −0.3 (6) | C18—C17—C22—C21 | 1.8 (6) |
C11—N2—C9—C3 | −179.2 (3) | C1—C17—C22—C21 | −178.9 (4) |
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 |
Experimental details
Crystal data | |
Chemical formula | C24H25N3O2S |
Mr | 419.53 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 292 |
a, b, c (Å) | 8.3905 (11), 9.9883 (13), 12.9549 (17) |
α, β, γ (°) | 91.375 (2), 94.789 (3), 96.121 (2) |
V (Å3) | 1075.2 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.32 × 0.28 × 0.22 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.942, 0.967 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10653, 3967, 2633 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.085, 0.184, 1.14 |
No. of reflections | 3967 |
No. of parameters | 274 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.24 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS86 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), PARST (Nardelli, 1995) and PLATON (Spek, 2003).
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 |
Acknowledgements
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.
References
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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).