organic compounds
7-Methyl-9-p-tolyl-4,9-dihydrofuro[3,4-b]quinolin-1(3H)-one
aSchool of Chemistry and Chemical Engineering, Institute of Pharmaceutical Engineering, Southeast University, Nanjing 210096, People's Republic of China
*Correspondence e-mail: scl_78@163.com
In the title compound, C19H17NO2, the dihydropyridine ring adopts a flattened boat conformation while the furanone ring is almost planar (r.m.s. deviation 0.018 Å). The molecules are linked into chains along the b axis by N—H⋯O intermolecular hydrogen bonds. In addition, C—H⋯π interactions involving the phenyl ring of the tolyl group as π acceptor are observed.
Related literature
For the biological activities of podophyllotoxin and its derivatives, see: Bosmans et al. (1989); Eycken et al. (1989); Hitosuyanagi et al. (1997, 1999); Lienard et al. (1991); Magedov et al. (2007); Poli & Giambastiani (2002); Tomioka et al. (1989, 1993); Tratrat et al. (2002).
Experimental
Crystal data
|
Refinement
|
Data collection: CrystalClear (Rigaku, 2000); cell CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003); 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.
Supporting information
10.1107/S1600536808041457/ci2738sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808041457/ci2738Isup2.hkl
The title compound was prepared by the reaction of 4-methylaniline (1 mmol) and 4-methylbenzaldehyde (1 mmol) with tetronic acid (1 mmol) in the presence of L-proline (0.1 mmol) in ethanol (2 ml) at 353 K. Crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a N,N-dimethylformamide and ethanol solution. 1H NMR (DMSO-d6, δ): 2.12 (3H, s, CH3), 2.22 (3H, s, CH3), 4.85 (1H, d, J = 16.0 Hz, CH), 4.91 (1H, s, CH), 4.94 (1H, d, J = 16.0 Hz, CH), 6.80–6.84 (2H, m, ArH), 6.93 (1H, d, J = 8.0 Hz, ArH), 7.04–7.08 (4H, m, ArH), 9.94 (1H, s, NH).
H atoms were placed in calculated positions (N-H = 0.87 Å and C-H = 0.94–0.99 Å), and included in the final cycles of
using a riding model, with Uiso(H) = 1.2–1.5 Ueq(C). A rotating group model was used for the methyl groups.Data collection: CrystalClear (Rigaku, 2000); cell
CrystalClear (Rigaku, 2000); data reduction: CrystalStructure (Rigaku/MSC, 2003); 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 (Sheldrick, 2008).C19H17NO2 | F(000) = 616 |
Mr = 291.34 | Dx = 1.317 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -P 2ybc | Cell parameters from 4940 reflections |
a = 9.178 (2) Å | θ = 3.3–25.3° |
b = 11.457 (2) Å | µ = 0.09 mm−1 |
c = 14.350 (4) Å | T = 223 K |
β = 103.124 (5)° | Block, colourless |
V = 1469.5 (6) Å3 | 0.60 × 0.48 × 0.45 mm |
Z = 4 |
Rigaku Mercury diffractometer | 2675 independent reflections |
Radiation source: fine-focus sealed tube | 2364 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 7.31 pixels mm-1 | θmax = 25.3°, θmin = 3.3° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (Jacobson, 1998) | k = −13→12 |
Tmin = 0.756, Tmax = 0.962 | l = −17→17 |
13947 measured reflections |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.16 | w = 1/[σ2(Fo2) + (0.0497P)2 + 0.6176P] where P = (Fo2 + 2Fc2)/3 |
2675 reflections | (Δ/σ)max = 0.001 |
202 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C19H17NO2 | V = 1469.5 (6) Å3 |
Mr = 291.34 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.178 (2) Å | µ = 0.09 mm−1 |
b = 11.457 (2) Å | T = 223 K |
c = 14.350 (4) Å | 0.60 × 0.48 × 0.45 mm |
β = 103.124 (5)° |
Rigaku Mercury diffractometer | 2675 independent reflections |
Absorption correction: multi-scan (Jacobson, 1998) | 2364 reflections with I > 2σ(I) |
Tmin = 0.756, Tmax = 0.962 | Rint = 0.034 |
13947 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.16 | Δρmax = 0.23 e Å−3 |
2675 reflections | Δρmin = −0.21 e Å−3 |
202 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 | ||
O1 | −0.06775 (18) | 0.28146 (14) | 0.77022 (11) | 0.0528 (4) | |
O2 | −0.09551 (18) | 0.13853 (14) | 0.66103 (12) | 0.0549 (5) | |
N1 | 0.14394 (19) | 0.50270 (15) | 0.68136 (12) | 0.0396 (4) | |
H1 | 0.1588 | 0.5617 | 0.7205 | 0.048* | |
C1 | 0.1948 (2) | 0.50585 (16) | 0.59568 (14) | 0.0343 (5) | |
C2 | 0.1821 (2) | 0.40751 (17) | 0.53741 (13) | 0.0329 (5) | |
C3 | 0.1160 (2) | 0.29193 (17) | 0.56127 (14) | 0.0342 (5) | |
H3 | 0.0327 | 0.2709 | 0.5069 | 0.041* | |
C4 | 0.0523 (2) | 0.31008 (18) | 0.64815 (14) | 0.0366 (5) | |
C5 | 0.0727 (2) | 0.40748 (18) | 0.70132 (14) | 0.0374 (5) | |
C6 | 0.2347 (2) | 0.41594 (18) | 0.45381 (14) | 0.0382 (5) | |
H6 | 0.2259 | 0.3505 | 0.4134 | 0.046* | |
C7 | 0.2994 (2) | 0.51643 (18) | 0.42757 (15) | 0.0400 (5) | |
C8 | 0.3088 (2) | 0.61316 (18) | 0.48745 (16) | 0.0424 (5) | |
H8 | 0.3511 | 0.6827 | 0.4710 | 0.051* | |
C9 | 0.2572 (2) | 0.60876 (18) | 0.57031 (16) | 0.0401 (5) | |
H9 | 0.2641 | 0.6750 | 0.6097 | 0.048* | |
C10 | 0.3607 (3) | 0.5198 (2) | 0.33889 (16) | 0.0513 (6) | |
H10A | 0.4686 | 0.5113 | 0.3565 | 0.077* | |
H10B | 0.3352 | 0.5938 | 0.3064 | 0.077* | |
H10C | 0.3178 | 0.4565 | 0.2966 | 0.077* | |
C11 | −0.0401 (2) | 0.2330 (2) | 0.68790 (16) | 0.0440 (5) | |
C12 | 0.0028 (3) | 0.3941 (2) | 0.78519 (16) | 0.0479 (6) | |
H12A | 0.0788 | 0.3961 | 0.8455 | 0.058* | |
H12B | −0.0709 | 0.4557 | 0.7860 | 0.058* | |
C13 | 0.2291 (2) | 0.19179 (16) | 0.57700 (13) | 0.0319 (4) | |
C14 | 0.3781 (2) | 0.20786 (18) | 0.62247 (15) | 0.0409 (5) | |
H14 | 0.4124 | 0.2829 | 0.6429 | 0.049* | |
C15 | 0.4770 (2) | 0.11455 (19) | 0.63815 (16) | 0.0437 (5) | |
H15 | 0.5776 | 0.1279 | 0.6687 | 0.052* | |
C16 | 0.4311 (2) | 0.00218 (17) | 0.60993 (14) | 0.0383 (5) | |
C17 | 0.2828 (2) | −0.01293 (18) | 0.56396 (15) | 0.0425 (5) | |
H17 | 0.2484 | −0.0879 | 0.5433 | 0.051* | |
C18 | 0.1838 (2) | 0.07991 (17) | 0.54770 (15) | 0.0394 (5) | |
H18 | 0.0837 | 0.0667 | 0.5161 | 0.047* | |
C19 | 0.5382 (3) | −0.0990 (2) | 0.62813 (17) | 0.0511 (6) | |
H19A | 0.5792 | −0.1118 | 0.5723 | 0.077* | |
H19B | 0.4856 | −0.1686 | 0.6408 | 0.077* | |
H19C | 0.6187 | −0.0820 | 0.6830 | 0.077* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0578 (10) | 0.0565 (10) | 0.0538 (10) | −0.0026 (8) | 0.0326 (8) | 0.0054 (8) |
O2 | 0.0594 (10) | 0.0468 (10) | 0.0643 (11) | −0.0111 (8) | 0.0259 (9) | 0.0068 (8) |
N1 | 0.0428 (10) | 0.0394 (10) | 0.0397 (10) | −0.0028 (8) | 0.0160 (8) | −0.0071 (8) |
C1 | 0.0297 (10) | 0.0376 (11) | 0.0370 (11) | 0.0023 (8) | 0.0104 (9) | 0.0015 (9) |
C2 | 0.0303 (10) | 0.0354 (11) | 0.0337 (10) | 0.0012 (8) | 0.0085 (8) | 0.0035 (8) |
C3 | 0.0328 (10) | 0.0368 (11) | 0.0343 (10) | −0.0020 (8) | 0.0104 (8) | −0.0007 (8) |
C4 | 0.0340 (10) | 0.0408 (11) | 0.0366 (11) | 0.0017 (9) | 0.0116 (9) | 0.0047 (9) |
C5 | 0.0313 (10) | 0.0456 (12) | 0.0370 (11) | 0.0033 (9) | 0.0111 (9) | 0.0021 (9) |
C6 | 0.0396 (11) | 0.0398 (11) | 0.0369 (11) | 0.0026 (9) | 0.0123 (9) | 0.0015 (9) |
C7 | 0.0359 (11) | 0.0454 (12) | 0.0400 (11) | 0.0018 (9) | 0.0114 (9) | 0.0112 (9) |
C8 | 0.0407 (12) | 0.0365 (11) | 0.0512 (13) | −0.0021 (9) | 0.0129 (10) | 0.0089 (10) |
C9 | 0.0385 (11) | 0.0340 (11) | 0.0481 (12) | 0.0002 (8) | 0.0103 (10) | −0.0023 (9) |
C10 | 0.0523 (14) | 0.0589 (15) | 0.0469 (13) | 0.0007 (11) | 0.0198 (11) | 0.0130 (11) |
C11 | 0.0407 (12) | 0.0475 (13) | 0.0478 (13) | 0.0029 (10) | 0.0184 (10) | 0.0087 (10) |
C12 | 0.0490 (13) | 0.0545 (14) | 0.0462 (13) | −0.0018 (10) | 0.0232 (11) | −0.0011 (11) |
C13 | 0.0363 (10) | 0.0334 (10) | 0.0283 (9) | −0.0030 (8) | 0.0122 (8) | 0.0000 (8) |
C14 | 0.0415 (12) | 0.0364 (11) | 0.0433 (12) | −0.0054 (9) | 0.0067 (9) | −0.0045 (9) |
C15 | 0.0369 (11) | 0.0479 (13) | 0.0449 (12) | −0.0005 (9) | 0.0065 (10) | −0.0002 (10) |
C16 | 0.0470 (12) | 0.0396 (12) | 0.0316 (10) | 0.0030 (9) | 0.0158 (9) | 0.0032 (8) |
C17 | 0.0502 (13) | 0.0344 (11) | 0.0438 (12) | −0.0068 (9) | 0.0123 (10) | −0.0035 (9) |
C18 | 0.0368 (11) | 0.0394 (11) | 0.0416 (11) | −0.0067 (9) | 0.0082 (9) | −0.0005 (9) |
C19 | 0.0589 (14) | 0.0472 (13) | 0.0496 (13) | 0.0105 (11) | 0.0172 (11) | 0.0042 (11) |
O1—C11 | 1.380 (3) | C8—H8 | 0.94 |
O1—C12 | 1.438 (3) | C9—H9 | 0.94 |
O2—C11 | 1.220 (3) | C10—H10A | 0.97 |
N1—C5 | 1.336 (3) | C10—H10B | 0.97 |
N1—C1 | 1.411 (3) | C10—H10C | 0.97 |
N1—H1 | 0.87 | C12—H12A | 0.98 |
C1—C2 | 1.392 (3) | C12—H12B | 0.98 |
C1—C9 | 1.395 (3) | C13—C18 | 1.383 (3) |
C2—C6 | 1.395 (3) | C13—C14 | 1.387 (3) |
C2—C3 | 1.528 (3) | C14—C15 | 1.387 (3) |
C3—C4 | 1.506 (3) | C14—H14 | 0.94 |
C3—C13 | 1.529 (3) | C15—C16 | 1.386 (3) |
C3—H3 | 0.99 | C15—H15 | 0.94 |
C4—C5 | 1.341 (3) | C16—C17 | 1.382 (3) |
C4—C11 | 1.430 (3) | C16—C19 | 1.504 (3) |
C5—C12 | 1.494 (3) | C17—C18 | 1.384 (3) |
C6—C7 | 1.386 (3) | C17—H17 | 0.94 |
C6—H6 | 0.94 | C18—H18 | 0.94 |
C7—C8 | 1.393 (3) | C19—H19A | 0.97 |
C7—C10 | 1.504 (3) | C19—H19B | 0.97 |
C8—C9 | 1.377 (3) | C19—H19C | 0.97 |
C11—O1—C12 | 108.95 (16) | C7—C10—H10C | 109.5 |
C5—N1—C1 | 118.85 (17) | H10A—C10—H10C | 109.5 |
C5—N1—H1 | 120.6 | H10B—C10—H10C | 109.5 |
C1—N1—H1 | 120.6 | O2—C11—O1 | 118.87 (19) |
C2—C1—C9 | 120.68 (18) | O2—C11—C4 | 131.6 (2) |
C2—C1—N1 | 120.25 (17) | O1—C11—C4 | 109.52 (19) |
C9—C1—N1 | 119.06 (18) | O1—C12—C5 | 103.48 (17) |
C1—C2—C6 | 117.57 (18) | O1—C12—H12A | 111.1 |
C1—C2—C3 | 123.37 (17) | C5—C12—H12A | 111.1 |
C6—C2—C3 | 119.06 (17) | O1—C12—H12B | 111.1 |
C4—C3—C2 | 108.32 (16) | C5—C12—H12B | 111.1 |
C4—C3—C13 | 111.04 (16) | H12A—C12—H12B | 109.0 |
C2—C3—C13 | 113.10 (15) | C18—C13—C14 | 117.52 (18) |
C4—C3—H3 | 108.1 | C18—C13—C3 | 120.23 (17) |
C2—C3—H3 | 108.1 | C14—C13—C3 | 122.24 (17) |
C13—C3—H3 | 108.1 | C13—C14—C15 | 120.86 (19) |
C5—C4—C11 | 107.79 (19) | C13—C14—H14 | 119.6 |
C5—C4—C3 | 123.77 (18) | C15—C14—H14 | 119.6 |
C11—C4—C3 | 128.43 (19) | C16—C15—C14 | 121.6 (2) |
N1—C5—C4 | 124.70 (19) | C16—C15—H15 | 119.2 |
N1—C5—C12 | 125.25 (19) | C14—C15—H15 | 119.2 |
C4—C5—C12 | 110.05 (19) | C17—C16—C15 | 117.18 (19) |
C7—C6—C2 | 122.99 (19) | C17—C16—C19 | 121.35 (19) |
C7—C6—H6 | 118.5 | C15—C16—C19 | 121.5 (2) |
C2—C6—H6 | 118.5 | C16—C17—C18 | 121.46 (19) |
C6—C7—C8 | 117.62 (19) | C16—C17—H17 | 119.3 |
C6—C7—C10 | 121.1 (2) | C18—C17—H17 | 119.3 |
C8—C7—C10 | 121.2 (2) | C13—C18—C17 | 121.37 (19) |
C9—C8—C7 | 121.21 (19) | C13—C18—H18 | 119.3 |
C9—C8—H8 | 119.4 | C17—C18—H18 | 119.3 |
C7—C8—H8 | 119.4 | C16—C19—H19A | 109.5 |
C8—C9—C1 | 119.9 (2) | C16—C19—H19B | 109.5 |
C8—C9—H9 | 120.0 | H19A—C19—H19B | 109.5 |
C1—C9—H9 | 120.0 | C16—C19—H19C | 109.5 |
C7—C10—H10A | 109.5 | H19A—C19—H19C | 109.5 |
C7—C10—H10B | 109.5 | H19B—C19—H19C | 109.5 |
H10A—C10—H10B | 109.5 | ||
C5—N1—C1—C2 | −5.5 (3) | C7—C8—C9—C1 | 0.3 (3) |
C5—N1—C1—C9 | 174.32 (18) | C2—C1—C9—C8 | −0.8 (3) |
C9—C1—C2—C6 | 0.3 (3) | N1—C1—C9—C8 | 179.35 (18) |
N1—C1—C2—C6 | −179.82 (17) | C12—O1—C11—O2 | −177.5 (2) |
C9—C1—C2—C3 | 179.55 (17) | C12—O1—C11—C4 | 1.7 (2) |
N1—C1—C2—C3 | −0.6 (3) | C5—C4—C11—O2 | 174.9 (2) |
C1—C2—C3—C4 | 7.1 (2) | C3—C4—C11—O2 | −3.7 (4) |
C6—C2—C3—C4 | −173.67 (17) | C5—C4—C11—O1 | −4.1 (2) |
C1—C2—C3—C13 | −116.4 (2) | C3—C4—C11—O1 | 177.31 (18) |
C6—C2—C3—C13 | 62.8 (2) | C11—O1—C12—C5 | 1.1 (2) |
C2—C3—C4—C5 | −8.9 (3) | N1—C5—C12—O1 | 175.80 (19) |
C13—C3—C4—C5 | 115.9 (2) | C4—C5—C12—O1 | −3.7 (2) |
C2—C3—C4—C11 | 169.54 (19) | C4—C3—C13—C18 | 93.7 (2) |
C13—C3—C4—C11 | −65.7 (3) | C2—C3—C13—C18 | −144.25 (18) |
C1—N1—C5—C4 | 4.0 (3) | C4—C3—C13—C14 | −84.7 (2) |
C1—N1—C5—C12 | −175.41 (19) | C2—C3—C13—C14 | 37.3 (2) |
C11—C4—C5—N1 | −174.73 (19) | C18—C13—C14—C15 | −0.4 (3) |
C3—C4—C5—N1 | 4.0 (3) | C3—C13—C14—C15 | 178.10 (19) |
C11—C4—C5—C12 | 4.8 (2) | C13—C14—C15—C16 | −0.5 (3) |
C3—C4—C5—C12 | −176.55 (18) | C14—C15—C16—C17 | 1.0 (3) |
C1—C2—C6—C7 | 0.7 (3) | C14—C15—C16—C19 | −179.2 (2) |
C3—C2—C6—C7 | −178.55 (18) | C15—C16—C17—C18 | −0.7 (3) |
C2—C6—C7—C8 | −1.2 (3) | C19—C16—C17—C18 | 179.6 (2) |
C2—C6—C7—C10 | 177.29 (19) | C14—C13—C18—C17 | 0.7 (3) |
C6—C7—C8—C9 | 0.7 (3) | C3—C13—C18—C17 | −177.80 (18) |
C10—C7—C8—C9 | −177.79 (19) | C16—C17—C18—C13 | −0.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.87 | 2.11 | 2.862 (2) | 144 |
C19—H19A···Cg1ii | 0.97 | 2.69 | 3.645 (3) | 167 |
Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C19H17NO2 |
Mr | 291.34 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 223 |
a, b, c (Å) | 9.178 (2), 11.457 (2), 14.350 (4) |
β (°) | 103.124 (5) |
V (Å3) | 1469.5 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.60 × 0.48 × 0.45 |
Data collection | |
Diffractometer | Rigaku Mercury diffractometer |
Absorption correction | Multi-scan (Jacobson, 1998) |
Tmin, Tmax | 0.756, 0.962 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13947, 2675, 2364 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.135, 1.16 |
No. of reflections | 2675 |
No. of parameters | 202 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.21 |
Computer programs: CrystalClear (Rigaku, 2000), CrystalStructure (Rigaku/MSC, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.87 | 2.11 | 2.862 (2) | 144 |
C19—H19A···Cg1ii | 0.97 | 2.69 | 3.645 (3) | 167 |
Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1, −y, −z+1. |
Acknowledgements
The authors are grateful to the Foundation of the Key Laboratory of Biotechnology of Medical Plants of Jiangsu Province for financial support.
References
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Podophyllotoxin is an antitumor lignan that inhibits microtubule assembly (Eycken et al., 1989; Tomioka et al., 1989; Bosmans et al., 1989). Because of mostly unsuccessfull attempts to use it for the treatment of human neoplasia and complicated side effects, extensive structural modifications have been performed in order to obtain more potent and less toxic anticancer agents (Tomioka et al., 1993; Lienard et al., 1991; Poli et al., 2002). Among them, 4-aza-podophyllotoxin (9-aryl-4,9-dihydrofuro [3,4-b]quinolin-1(3H)-one) derivatives reported as powerful DNA topoisomerase II inhibitors, have recently attached considerable interest (Hitosuyanagi et al., 1997; Hitosuyanagi et al., 1999; Tratrat et al., 2002; Magedov et al., 2007). We report here the crystal structure of the title compound, which was synthesized by the three-component reaction of 4-methylaniline with 4-methylbenzaldehyde and tetronic acid catalyzed by L-proline using ethanol as solvent at 353 K.
In the title compound, the dihydropyridine ring (C1-C5/N1) adopts a flattened boat conformation, with atoms C3 and N1 deviating from the C1/C2/C4/C5 plane (r.m.s. deviation 0.009 Å) by 0.102 (3) and 0.050 (3) Å, respectively (Fig. 1). The five-membered ring is almost planar (r.m.s. deviation 0.018 Å). The dihedral angle between C1/C2/C6/C7-C9 and C1/C2/C4/C5 planes is 2.9 (1)° and that between C1/C2/C4/C5 and C13-C18 plane is 79.77 (7)°.
The molecules are linked into chains (Fig.2) along the b axis by N—H···O intermolecular hydrogen bonds (Table 1). In addition, C—H···π interactions involving the phenyl ring of the tolyl group are observed.