Acta Cryst. (2009). E65, o1319 [ doi:10.1107/S1600536809017942 ]
In the title compound, C18H15NO3, the pyridine-2,6-dione ring adopts an envelope conformation. The phenyl ring lies approximately perpendicular to the mean plane of the pyridine-2,6-dione ring [dihedral angle = 81.5 (1)°], while the methoxyphenyl ring is tilted to the same plane by a dihedral angle of 34.8 (1)°. Intermolecular C-H
O interactions link the molecules into chains along [100].
The title compound was prepared by microwave treatment of 3-(4-methoxyphenyl)-2-pentene-1,5-dioic acid with acetic anhydride to form the corresponding dione, which was then reacted further with aniline to give the resultant compound (yield 96%). 1H NMR (DMSO): δ 6.98 (m, 9H), 3.87 (s, 3H), 3.97(s, 2H), 6.67 (s, 1H).
H atoms were placed geometrically with C—H = 0.93–0.97 Å and refined as riding with Uiso(H) = 1.2 or 1.5 Ueq(C).
Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2009).
![[Figure 1]](./bi2366fig1thm.gif)
| Fig. 1. Molecular structure with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius. |
![[Figure 2]](./bi2366fig2thm.gif)
| Fig. 2. Packing diagram viewed down the c axis. The dotted lines indicate intermolecular C—H···O interactions. H atoms not involved in these interactions are omitted. |
![[Figure 3]](./bi2366fig3thm.gif)
| Fig. 3. Packing diagram viewed down the a axis. The dotted lines indicate intermolecular C—H···π and π···π interactions. H atoms not involved in these interactions are omitted. |
| C18H15NO3 | Z = 2 |
| Mr = 293.31 | F000 = 308 |
| Triclinic, P1 | Dx = 1.356 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 7.4652 (5) Å | Cell parameters from 2604 reflections |
| b = 9.0885 (7) Å | θ = 2.4–28.0º |
| c = 11.1181 (8) Å | µ = 0.09 mm−1 |
| α = 77.384 (1)º | T = 292 K |
| β = 88.747 (2)º | Block, colourless |
| γ = 77.493 (1)º | 0.52 × 0.41 × 0.32 mm |
| V = 718.40 (9) Å3 |
| Bruker SMART APEX CCD diffractometer | 2714 independent reflections |
| Radiation source: fine-focus sealed tube | 2233 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.017 |
| T = 292 K | θmax = 25.7º |
| φ and ω scans | θmin = 1.9º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
| Tmin = 0.921, Tmax = 0.970 | k = −11→11 |
| 7298 measured reflections | l = −13→13 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
| wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0537P)2 + 0.2183P] where P = (Fo2 + 2Fc2)/3 |
| S = 0.91 | (Δ/σ)max < 0.001 |
| 2714 reflections | Δρmax = 0.15 e Å−3 |
| 200 parameters | Δρmin = −0.17 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C18H15NO3 | γ = 77.493 (1)º |
| Mr = 293.31 | V = 718.40 (9) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 7.4652 (5) Å | Mo Kα |
| b = 9.0885 (7) Å | µ = 0.09 mm−1 |
| c = 11.1181 (8) Å | T = 292 K |
| α = 77.384 (1)º | 0.52 × 0.41 × 0.32 mm |
| β = 88.747 (2)º |
| Bruker SMART APEX CCD diffractometer | 2714 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2233 reflections with I > 2σ(I) |
| Tmin = 0.921, Tmax = 0.970 | Rint = 0.017 |
| 7298 measured reflections |
| R[F2 > 2σ(F2)] = 0.040 | 200 parameters |
| wR(F2) = 0.105 | H-atom parameters constrained |
| S = 0.91 | Δρmax = 0.15 e Å−3 |
| 2714 reflections | Δρmin = −0.17 e Å−3 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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 | 0.43237 (14) | 0.81573 (14) | −0.09890 (10) | 0.0584 (4) | |
| O2 | 1.00465 (13) | 0.63224 (13) | 0.07261 (10) | 0.0538 (4) | |
| O3 | 0.28108 (15) | 0.25107 (13) | 0.62184 (10) | 0.0569 (4) | |
| N1 | 0.72144 (15) | 0.72212 (13) | −0.01738 (10) | 0.0388 (4) | |
| C1 | 0.49575 (18) | 0.45771 (15) | 0.29553 (12) | 0.0369 (4) | |
| C2 | 0.56872 (18) | 0.54010 (15) | 0.18235 (12) | 0.0370 (4) | |
| C3 | 0.3591 (2) | 0.31101 (17) | 0.51532 (13) | 0.0418 (5) | |
| C4 | 0.46008 (19) | 0.63892 (17) | 0.09213 (13) | 0.0420 (5) | |
| C5 | 0.5880 (2) | 0.31397 (17) | 0.36111 (13) | 0.0428 (5) | |
| C6 | 0.33201 (19) | 0.52602 (17) | 0.34314 (13) | 0.0432 (5) | |
| C7 | 0.79229 (18) | 0.82360 (16) | −0.11708 (13) | 0.0387 (4) | |
| C8 | 0.2655 (2) | 0.45429 (18) | 0.45097 (14) | 0.0465 (5) | |
| C9 | 0.8359 (2) | 0.95658 (17) | −0.09782 (14) | 0.0462 (5) | |
| C10 | 0.53018 (19) | 0.73075 (16) | −0.01525 (13) | 0.0406 (4) | |
| C11 | 0.84395 (19) | 0.62585 (16) | 0.07338 (13) | 0.0397 (5) | |
| C12 | 0.77132 (19) | 0.51251 (18) | 0.16928 (13) | 0.0446 (5) | |
| C13 | 0.5210 (2) | 0.24011 (17) | 0.46966 (13) | 0.0449 (5) | |
| C14 | 0.8175 (2) | 0.78459 (18) | −0.23010 (14) | 0.0475 (5) | |
| C15 | 0.9349 (2) | 1.0118 (2) | −0.30544 (16) | 0.0576 (6) | |
| C16 | 0.8880 (2) | 0.8799 (2) | −0.32436 (15) | 0.0567 (6) | |
| C17 | 0.3837 (3) | 0.1142 (2) | 0.70023 (15) | 0.0585 (6) | |
| C18 | 0.9086 (2) | 1.04971 (19) | −0.19256 (16) | 0.0541 (6) | |
| H4 | 0.33372 | 0.64938 | 0.09840 | 0.0504* | |
| H5 | 0.69755 | 0.26599 | 0.33143 | 0.0513* | |
| H6 | 0.26674 | 0.62196 | 0.30098 | 0.0518* | |
| H8 | 0.15638 | 0.50240 | 0.48115 | 0.0558* | |
| H9 | 0.81648 | 0.98333 | −0.02173 | 0.0554* | |
| H12A | 0.82601 | 0.50985 | 0.24829 | 0.0536* | |
| H12B | 0.81319 | 0.41097 | 0.15146 | 0.0536* | |
| H13 | 0.58454 | 0.14339 | 0.51153 | 0.0539* | |
| H14 | 0.78734 | 0.69496 | −0.24275 | 0.0570* | |
| H15 | 0.98420 | 1.07481 | −0.36893 | 0.0692* | |
| H16 | 0.90396 | 0.85501 | −0.40126 | 0.0680* | |
| H17A | 0.50078 | 0.13092 | 0.72080 | 0.0878* | |
| H17B | 0.31768 | 0.08907 | 0.77430 | 0.0878* | |
| H17C | 0.40147 | 0.03050 | 0.65833 | 0.0878* | |
| H18 | 0.94004 | 1.13880 | −0.17976 | 0.0650* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0395 (6) | 0.0727 (8) | 0.0496 (6) | −0.0081 (5) | −0.0031 (5) | 0.0114 (6) |
| O2 | 0.0335 (6) | 0.0649 (7) | 0.0596 (7) | −0.0153 (5) | −0.0013 (5) | −0.0016 (5) |
| O3 | 0.0537 (7) | 0.0605 (7) | 0.0484 (6) | −0.0121 (5) | 0.0116 (5) | 0.0042 (5) |
| N1 | 0.0332 (6) | 0.0435 (7) | 0.0380 (6) | −0.0104 (5) | 0.0028 (5) | −0.0035 (5) |
| C1 | 0.0359 (7) | 0.0391 (7) | 0.0369 (7) | −0.0111 (6) | 0.0015 (6) | −0.0081 (6) |
| C2 | 0.0363 (7) | 0.0381 (7) | 0.0382 (7) | −0.0104 (6) | 0.0043 (6) | −0.0100 (6) |
| C3 | 0.0423 (8) | 0.0474 (8) | 0.0372 (8) | −0.0171 (7) | 0.0044 (6) | −0.0056 (6) |
| C4 | 0.0311 (7) | 0.0512 (9) | 0.0434 (8) | −0.0120 (6) | 0.0038 (6) | −0.0071 (7) |
| C5 | 0.0380 (8) | 0.0453 (8) | 0.0425 (8) | −0.0055 (6) | 0.0057 (6) | −0.0083 (6) |
| C6 | 0.0403 (8) | 0.0391 (8) | 0.0454 (8) | −0.0057 (6) | 0.0038 (6) | −0.0022 (6) |
| C7 | 0.0315 (7) | 0.0421 (8) | 0.0401 (8) | −0.0086 (6) | 0.0009 (6) | −0.0035 (6) |
| C8 | 0.0379 (8) | 0.0510 (9) | 0.0481 (9) | −0.0074 (7) | 0.0092 (7) | −0.0085 (7) |
| C9 | 0.0458 (9) | 0.0458 (8) | 0.0470 (9) | −0.0102 (7) | −0.0020 (7) | −0.0096 (7) |
| C10 | 0.0351 (7) | 0.0454 (8) | 0.0393 (8) | −0.0074 (6) | 0.0007 (6) | −0.0061 (6) |
| C11 | 0.0345 (8) | 0.0450 (8) | 0.0401 (8) | −0.0086 (6) | 0.0033 (6) | −0.0104 (6) |
| C12 | 0.0362 (8) | 0.0514 (9) | 0.0414 (8) | −0.0072 (6) | 0.0013 (6) | −0.0021 (7) |
| C13 | 0.0465 (8) | 0.0407 (8) | 0.0434 (8) | −0.0067 (7) | −0.0006 (7) | −0.0029 (6) |
| C14 | 0.0451 (9) | 0.0538 (9) | 0.0471 (9) | −0.0167 (7) | 0.0060 (7) | −0.0130 (7) |
| C15 | 0.0453 (9) | 0.0647 (11) | 0.0555 (10) | −0.0196 (8) | 0.0034 (7) | 0.0099 (8) |
| C16 | 0.0498 (10) | 0.0783 (12) | 0.0418 (9) | −0.0183 (9) | 0.0090 (7) | −0.0094 (8) |
| C17 | 0.0640 (11) | 0.0593 (10) | 0.0460 (9) | −0.0164 (9) | 0.0044 (8) | 0.0046 (8) |
| C18 | 0.0501 (9) | 0.0446 (9) | 0.0655 (11) | −0.0177 (7) | −0.0054 (8) | 0.0006 (8) |
| O1—C10 | 1.2109 (18) | C11—C12 | 1.493 (2) |
| O2—C11 | 1.2133 (18) | C14—C16 | 1.379 (2) |
| O3—C3 | 1.3653 (18) | C15—C16 | 1.378 (2) |
| O3—C17 | 1.427 (2) | C15—C18 | 1.372 (2) |
| N1—C7 | 1.4485 (18) | C4—H4 | 0.930 |
| N1—C10 | 1.4129 (19) | C5—H5 | 0.930 |
| N1—C11 | 1.3886 (18) | C6—H6 | 0.930 |
| C1—C2 | 1.4751 (19) | C8—H8 | 0.930 |
| C1—C5 | 1.389 (2) | C9—H9 | 0.930 |
| C1—C6 | 1.395 (2) | C12—H12A | 0.970 |
| C2—C4 | 1.341 (2) | C12—H12B | 0.970 |
| C2—C12 | 1.488 (2) | C13—H13 | 0.930 |
| C3—C8 | 1.384 (2) | C14—H14 | 0.930 |
| C3—C13 | 1.383 (2) | C15—H15 | 0.930 |
| C4—C10 | 1.457 (2) | C16—H16 | 0.930 |
| C5—C13 | 1.387 (2) | C17—H17A | 0.960 |
| C6—C8 | 1.372 (2) | C17—H17B | 0.960 |
| C7—C9 | 1.378 (2) | C17—H17C | 0.960 |
| C7—C14 | 1.377 (2) | C18—H18 | 0.930 |
| C9—C18 | 1.380 (2) | ||
| O1···C14 | 3.1810 (19) | C17···H13 | 2.5500 |
| O1···C17i | 3.073 (2) | C18···H17Ai | 3.1000 |
| O1···C5ii | 3.3926 (19) | C18···H6iv | 2.9800 |
| O2···C9 | 3.1501 (19) | H4···O2x | 2.5200 |
| O2···O2iii | 3.1878 (16) | H4···C6 | 2.7100 |
| O2···C11iii | 3.1383 (19) | H4···H6 | 2.2700 |
| O1···H9iv | 2.8400 | H5···C12 | 2.7000 |
| O1···H17Bi | 2.5500 | H5···H12A | 2.5800 |
| O2···H4v | 2.5200 | H5···H12B | 2.4000 |
| O2···H12Biii | 2.8700 | H5···C16iii | 3.1000 |
| O2···H18vi | 2.7200 | H6···C4 | 2.7000 |
| O3···H12Avii | 2.8300 | H6···H4 | 2.2700 |
| C2···C10ii | 3.592 (2) | H6···C18iv | 2.9800 |
| C3···C6vii | 3.556 (2) | H6···H18iv | 2.5100 |
| C4···C4ii | 3.533 (2) | H8···H8xi | 2.3700 |
| C5···O1ii | 3.3926 (19) | H9···O1iv | 2.8400 |
| C6···C3vii | 3.556 (2) | H12A···C5 | 2.8600 |
| C9···O2 | 3.1501 (19) | H12A···H5 | 2.5800 |
| C10···C2ii | 3.592 (2) | H12A···O3vii | 2.8300 |
| C11···C11iii | 3.533 (2) | H12B···C5 | 2.9300 |
| C11···O2iii | 3.1383 (19) | H12B···H5 | 2.4000 |
| C12···C14iii | 3.588 (2) | H12B···O2iii | 2.8700 |
| C14···O1 | 3.1810 (19) | H12B···C14iii | 2.9700 |
| C14···C12iii | 3.588 (2) | H13···C17 | 2.5500 |
| C17···O1viii | 3.073 (2) | H13···H17A | 2.3800 |
| C1···H14ii | 2.9000 | H13···H17C | 2.3200 |
| C4···H6 | 2.7000 | H14···C1ii | 2.9000 |
| C5···H12A | 2.8600 | H14···C6ii | 2.8100 |
| C5···H12B | 2.9300 | H14···C8ii | 3.0000 |
| C6···H4 | 2.7100 | H17A···C13 | 2.7600 |
| C6···H14ii | 2.8100 | H17A···C18viii | 3.1000 |
| C8···H14ii | 3.0000 | H17A···H13 | 2.3800 |
| C12···H5 | 2.7000 | H17B···O1viii | 2.5500 |
| C13···H17Cix | 3.0500 | H17C···C13 | 2.7800 |
| C13···H17C | 2.7800 | H17C···H13 | 2.3200 |
| C13···H17A | 2.7600 | H17C···C13ix | 3.0500 |
| C14···H12Biii | 2.9700 | H18···O2vi | 2.7200 |
| C16···H5iii | 3.1000 | H18···H6iv | 2.5100 |
| C3—O3—C17 | 117.96 (13) | C9—C18—C15 | 120.48 (16) |
| C7—N1—C10 | 118.12 (11) | C2—C4—H4 | 118.00 |
| C7—N1—C11 | 118.34 (11) | C10—C4—H4 | 118.00 |
| C10—N1—C11 | 123.50 (12) | C1—C5—H5 | 119.00 |
| C2—C1—C5 | 122.31 (13) | C13—C5—H5 | 119.00 |
| C2—C1—C6 | 120.23 (12) | C1—C6—H6 | 119.00 |
| C5—C1—C6 | 117.42 (13) | C8—C6—H6 | 119.00 |
| C1—C2—C4 | 122.65 (13) | C3—C8—H8 | 120.00 |
| C1—C2—C12 | 118.18 (12) | C6—C8—H8 | 120.00 |
| C4—C2—C12 | 119.17 (13) | C7—C9—H9 | 120.00 |
| O3—C3—C8 | 115.66 (13) | C18—C9—H9 | 120.00 |
| O3—C3—C13 | 125.04 (14) | C2—C12—H12A | 108.00 |
| C8—C3—C13 | 119.30 (14) | C2—C12—H12B | 108.00 |
| C2—C4—C10 | 123.24 (13) | C11—C12—H12A | 108.00 |
| C1—C5—C13 | 121.73 (14) | C11—C12—H12B | 108.00 |
| C1—C6—C8 | 121.22 (14) | H12A—C12—H12B | 107.00 |
| N1—C7—C9 | 120.00 (13) | C3—C13—H13 | 120.00 |
| N1—C7—C14 | 119.30 (13) | C5—C13—H13 | 120.00 |
| C9—C7—C14 | 120.69 (14) | C7—C14—H14 | 120.00 |
| C3—C8—C6 | 120.67 (14) | C16—C14—H14 | 120.00 |
| C7—C9—C18 | 119.36 (14) | C16—C15—H15 | 120.00 |
| O1—C10—N1 | 119.66 (13) | C18—C15—H15 | 120.00 |
| O1—C10—C4 | 123.20 (13) | C14—C16—H16 | 120.00 |
| N1—C10—C4 | 117.10 (12) | C15—C16—H16 | 120.00 |
| O2—C11—N1 | 120.80 (13) | O3—C17—H17A | 109.00 |
| O2—C11—C12 | 121.64 (13) | O3—C17—H17B | 109.00 |
| N1—C11—C12 | 117.54 (12) | O3—C17—H17C | 109.00 |
| C2—C12—C11 | 117.14 (13) | H17A—C17—H17B | 109.00 |
| C3—C13—C5 | 119.65 (14) | H17A—C17—H17C | 110.00 |
| C7—C14—C16 | 119.27 (15) | H17B—C17—H17C | 109.00 |
| C16—C15—C18 | 119.70 (16) | C9—C18—H18 | 120.00 |
| C14—C16—C15 | 120.49 (15) | C15—C18—H18 | 120.00 |
| C17—O3—C3—C8 | −171.64 (14) | C1—C2—C4—C10 | 174.69 (13) |
| C17—O3—C3—C13 | 8.0 (2) | C12—C2—C4—C10 | −4.8 (2) |
| C10—N1—C7—C9 | 100.50 (16) | C1—C2—C12—C11 | −163.73 (12) |
| C10—N1—C7—C14 | −80.33 (17) | C4—C2—C12—C11 | 15.8 (2) |
| C11—N1—C7—C9 | −77.12 (17) | O3—C3—C8—C6 | 179.52 (14) |
| C11—N1—C7—C14 | 102.05 (16) | C13—C3—C8—C6 | −0.1 (2) |
| C7—N1—C10—O1 | 3.7 (2) | O3—C3—C13—C5 | −178.98 (14) |
| C7—N1—C10—C4 | −174.06 (12) | C8—C3—C13—C5 | 0.6 (2) |
| C11—N1—C10—O1 | −178.78 (14) | C2—C4—C10—O1 | 177.20 (15) |
| C11—N1—C10—C4 | 3.4 (2) | C2—C4—C10—N1 | −5.1 (2) |
| C7—N1—C11—O2 | 3.7 (2) | C1—C5—C13—C3 | −0.6 (2) |
| C7—N1—C11—C12 | −174.81 (12) | C1—C6—C8—C3 | −0.4 (2) |
| C10—N1—C11—O2 | −173.76 (13) | N1—C7—C9—C18 | 178.01 (13) |
| C10—N1—C11—C12 | 7.7 (2) | C14—C7—C9—C18 | −1.2 (2) |
| C5—C1—C2—C4 | 151.27 (15) | N1—C7—C14—C16 | −178.87 (13) |
| C5—C1—C2—C12 | −29.3 (2) | C9—C7—C14—C16 | 0.3 (2) |
| C6—C1—C2—C4 | −31.1 (2) | C7—C9—C18—C15 | 0.9 (2) |
| C6—C1—C2—C12 | 148.33 (14) | O2—C11—C12—C2 | 164.44 (14) |
| C2—C1—C5—C13 | 177.76 (14) | N1—C11—C12—C2 | −17.04 (19) |
| C6—C1—C5—C13 | 0.1 (2) | C7—C14—C16—C15 | 0.8 (2) |
| C2—C1—C6—C8 | −177.30 (14) | C18—C15—C16—C14 | −1.0 (2) |
| C5—C1—C6—C8 | 0.4 (2) | C16—C15—C18—C9 | 0.1 (2) |
| Symmetry codes: (i) x, y+1, z−1; (ii) −x+1, −y+1, −z; (iii) −x+2, −y+1, −z; (iv) −x+1, −y+2, −z; (v) x+1, y, z; (vi) −x+2, −y+2, −z; (vii) −x+1, −y+1, −z+1; (viii) x, y−1, z+1; (ix) −x+1, −y, −z+1; (x) x−1, y, z; (xi) −x, −y+1, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C4—H4···O2x | 0.93 | 2.52 | 3.4260 (18) | 164.00 |
| C17—H17B···O1viii | 0.96 | 2.55 | 3.073 (2) | 114.00 |
| Symmetry codes: (x) x−1, y, z; (viii) x, y−1, z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C4—H4···O2i | 0.93 | 2.52 | 3.4260 (18) | 164.00 |
| C17—H17B···O1ii | 0.96 | 2.55 | 3.073 (2) | 114.00 |
| Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z+1. |
We thank the Department of Science and Technology, India, for use of the CCD facility set up under the IRHPA–DST program at IISc.
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The title compound belongs to the pyridine-2,6-dione family (Kon & Nanji, 1933). Pyridine-2,6-diones have a π-conjugated system and an extremely reactive methylene group, which has been exploited to carry out various condensations to form fused ring systems. The Mannich reaction is one of the important processes in medicinal chemistry that introduces an aminomethyl group, which acts as a pharmacophore when introduced into an appropriate substrate, and the title compound has been exploited via this reaction to form a wide array of compounds.
In the crystal structure, the pyridine-2,6-dione ring [N1/C10/C4/C2/C12/C11] adopts an envelope conformation (Cremer & Pople, 1975) with puckering parameters q2 = 0.1394 (15)°, q3 = 0.0581 (15)°, φ = 247.1 (6)°, puckering amplitude Q = 0.1510 (16) Å. The phenyl ring is nearly perpendicular to the pyridine-2,6-dione ring (torsion angle C11—N1—C7—C9 = 100.49 °) while the methoxy phenyl ring is tilted to the plane of the heterocyclic ring with a torsion angle C4—C2—C1—C6 = 31.14 °. Within the aryl rings, the C—C bonds are in the range of 1.343 (3) to 1.381 (3) Å, which is in accordance with those found in similar structures. The C—N single bonds (1.388 (3) to 1.448 (3) Å), C—O single bonds (1.365 (3) to 1.426 (3) Å), and C=O double bonds (1.213 (3) to 1.220 (2) Å) are within the usual range. The structure contains intermolecular C—H···O hydrogen bonds (see Table and Figure 2) which link the molecules into chains along the a axis. Alternating C—H···π and π···π interactions are also present (Figure 3).