Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270108000504/gd3181sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270108000504/gd3181Isup2.hkl |
CCDC reference: 681568
The general synthetics procedure is described by Hubert et al. (1975). N-(4-Methoxyphenyl)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboximide, (I) (0.77 g, 2.84 mmol), prepared from furan and N-(4-methoxyphenyl)maleimide, was reduced in ethanol solution (250 ml) with 0.94 g of Na(BH4) added in small portions (at intervals of 15 min) at 252 K over a period of 2 h. The excess of Na(BH4) was destroyed in 15–30 min at 5 K above the reaction temperature by adding aqueous HCl (2 mol dm-3) until the pH reached 3.0. The mixture was stirred for an additional 45–60 min at the same temperature and poured into water. After extraction with dichloromethane, the organic layer was separated, dried over Na2(SO4) and filtered; the solvent was removed under reduced pressure to give a white solid that was purified by column chromatography [silica gel, n-hexane/ethyl acetate (1:2, v/v)] to give white crystals in 84% yield.
NMR (DMSO): δ(H) 2.11–2.13 (d, J = 7.02 Hz, 1H, H2), 2.73–2.75 (d, J = 7.02 Hz, 1H, H6), 3.72 (s, 3H, OCH3), 4.97 (s, 1H, H1), 5.10 (s, 1H, H7), 5.25–5.27 (d, J = 7.8 Hz, 1H, H5), 6.36–6.38 (d, J = 7.8 Hz, 1H, OH exchange with D2O), 6.44–6.48 (m, 2H, H8 and H9), 6.90–6.92 (d, J = 9.36 Hz, 2H, aromatic), 7.36–7.39 (d, J = 9.36 Hz, 2H, aromatic); δ(C) 47.42 (C6), 49.38 (C2), 55.72 (OCH3), 81.35 (C7), 82.56 (C1), 88.21 (C5), 114.84 (Car), 127.08 (Car), 136.80 (C8 and C9), 137.01 (Cq—N). FT–IR (KBr): ν 3347 (OH), 3074, 3021, 2954, 2934 and 2833, 1672 (C═O), 1609 and 1513 (aromatic, C═C), 1445, 1414, 1306, 1252 (C–OCH3), 1182 (C—O stretching), 1036 (C—N), 829 cm-1.
All H atoms bonded to C atoms were treated as riding atoms, with C—H distances in the range 0.93–0.98 Å and with Uiso(H) = kUeq(C), where k = 1.5 for the methyl group and 1.2 for all other H atoms. The position of the hydroxy H atom was obtained from a difference map, and its parameters were freely refined.
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).
C15H15NO4 | F(000) = 576 |
Mr = 273.28 | Dx = 1.363 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8698 reflections |
a = 11.2076 (11) Å | θ = 2.2–27.9° |
b = 8.4910 (7) Å | µ = 0.10 mm−1 |
c = 14.1867 (15) Å | T = 293 K |
β = 99.457 (8)° | Prismatic stick, colorless |
V = 1331.7 (2) Å3 | 0.60 × 0.32 × 0.05 mm |
Z = 4 |
Stoe IPDSII diffractometer | 2600 independent reflections |
Radiation source: fine-focus sealed tube | 1497 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.070 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.8° |
rotation method scans | h = −13→13 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −10→10 |
Tmin = 0.952, Tmax = 0.993 | l = −17→17 |
9348 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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0472P)2] where P = (Fo2 + 2Fc2)/3 |
2600 reflections | (Δ/σ)max < 0.001 |
185 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C15H15NO4 | V = 1331.7 (2) Å3 |
Mr = 273.28 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.2076 (11) Å | µ = 0.10 mm−1 |
b = 8.4910 (7) Å | T = 293 K |
c = 14.1867 (15) Å | 0.60 × 0.32 × 0.05 mm |
β = 99.457 (8)° |
Stoe IPDSII diffractometer | 2600 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 1497 reflections with I > 2σ(I) |
Tmin = 0.952, Tmax = 0.993 | Rint = 0.070 |
9348 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | Δρmax = 0.14 e Å−3 |
2600 reflections | Δρmin = −0.16 e Å−3 |
185 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 | ||
C1 | 0.4207 (2) | 0.7677 (2) | 0.58436 (14) | 0.0476 (5) | |
H1 | 0.3926 | 0.6872 | 0.5363 | 0.057* | |
C2 | 0.55500 (19) | 0.7981 (2) | 0.58383 (14) | 0.0480 (5) | |
H2 | 0.5707 | 0.9084 | 0.5697 | 0.058* | |
C3 | 0.6123 (2) | 0.6838 (2) | 0.51904 (15) | 0.0549 (6) | |
H3 | 0.5661 | 0.6698 | 0.4547 | 0.066* | |
C4 | 0.7415 (2) | 0.7338 (3) | 0.52216 (18) | 0.0653 (7) | |
H4 | 0.7744 | 0.7852 | 0.4745 | 0.078* | |
C5 | 0.7997 (2) | 0.6883 (3) | 0.60845 (19) | 0.0655 (6) | |
H5 | 0.8813 | 0.7006 | 0.6330 | 0.079* | |
C6 | 0.7044 (2) | 0.6135 (2) | 0.65641 (16) | 0.0558 (6) | |
H6 | 0.7349 | 0.5411 | 0.7086 | 0.067* | |
C7 | 0.6221 (2) | 0.7482 (2) | 0.68316 (14) | 0.0499 (5) | |
H7 | 0.6686 | 0.8348 | 0.7170 | 0.060* | |
C8 | 0.5260 (2) | 0.6884 (2) | 0.73519 (15) | 0.0510 (5) | |
C9 | 0.3055 (2) | 0.6507 (2) | 0.70667 (15) | 0.0481 (5) | |
C10 | 0.2817 (2) | 0.6759 (2) | 0.79729 (16) | 0.0590 (6) | |
H10 | 0.3375 | 0.7300 | 0.8413 | 0.071* | |
C11 | 0.1757 (2) | 0.6219 (3) | 0.82413 (17) | 0.0653 (7) | |
H11 | 0.1611 | 0.6383 | 0.8860 | 0.078* | |
C12 | 0.0916 (2) | 0.5435 (3) | 0.75853 (18) | 0.0631 (6) | |
C13 | 0.1142 (2) | 0.5210 (3) | 0.66735 (19) | 0.0681 (7) | |
H13 | 0.0574 | 0.4692 | 0.6228 | 0.082* | |
C14 | 0.2197 (2) | 0.5741 (3) | 0.64107 (16) | 0.0594 (6) | |
H14 | 0.2337 | 0.5586 | 0.5789 | 0.071* | |
C15 | −0.0454 (3) | 0.5065 (4) | 0.8657 (2) | 0.0981 (10) | |
H15A | −0.1215 | 0.4569 | 0.8692 | 0.147* | |
H15B | −0.0520 | 0.6177 | 0.8760 | 0.147* | |
H15C | 0.0160 | 0.4631 | 0.9138 | 0.147* | |
N1 | 0.41634 (17) | 0.70217 (19) | 0.67952 (11) | 0.0489 (4) | |
O1 | 0.34588 (15) | 0.89990 (18) | 0.56653 (11) | 0.0569 (4) | |
O2 | 0.54368 (16) | 0.63113 (19) | 0.81618 (11) | 0.0690 (5) | |
O3 | 0.62555 (14) | 0.54348 (15) | 0.57720 (10) | 0.0576 (4) | |
O4 | −0.01544 (17) | 0.4810 (3) | 0.77786 (14) | 0.0877 (6) | |
H1A | 0.375 (3) | 0.975 (4) | 0.607 (2) | 0.098 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0582 (15) | 0.0412 (10) | 0.0425 (10) | −0.0002 (9) | 0.0053 (9) | 0.0036 (8) |
C2 | 0.0541 (15) | 0.0391 (10) | 0.0501 (12) | −0.0028 (9) | 0.0065 (10) | 0.0068 (9) |
C3 | 0.0619 (16) | 0.0550 (12) | 0.0472 (12) | 0.0018 (11) | 0.0072 (10) | 0.0024 (10) |
C4 | 0.0659 (18) | 0.0617 (14) | 0.0714 (16) | 0.0013 (12) | 0.0205 (13) | 0.0007 (12) |
C5 | 0.0530 (16) | 0.0598 (14) | 0.0829 (17) | 0.0040 (12) | 0.0089 (13) | −0.0055 (13) |
C6 | 0.0604 (16) | 0.0470 (11) | 0.0558 (13) | 0.0020 (10) | −0.0032 (11) | 0.0015 (10) |
C7 | 0.0564 (15) | 0.0406 (10) | 0.0495 (12) | −0.0041 (9) | −0.0003 (10) | −0.0033 (9) |
C8 | 0.0645 (16) | 0.0389 (10) | 0.0479 (12) | 0.0003 (10) | 0.0046 (11) | 0.0007 (9) |
C9 | 0.0567 (15) | 0.0397 (10) | 0.0481 (12) | 0.0019 (9) | 0.0088 (10) | 0.0050 (9) |
C10 | 0.0690 (17) | 0.0536 (13) | 0.0550 (14) | −0.0013 (11) | 0.0118 (12) | −0.0017 (10) |
C11 | 0.0760 (19) | 0.0684 (14) | 0.0559 (14) | 0.0103 (13) | 0.0236 (13) | 0.0061 (11) |
C12 | 0.0558 (17) | 0.0645 (14) | 0.0698 (17) | 0.0027 (12) | 0.0126 (12) | 0.0130 (12) |
C13 | 0.0618 (18) | 0.0724 (15) | 0.0691 (16) | −0.0066 (13) | 0.0077 (13) | −0.0015 (13) |
C14 | 0.0633 (17) | 0.0625 (13) | 0.0517 (13) | −0.0025 (12) | 0.0075 (11) | −0.0008 (11) |
C15 | 0.075 (2) | 0.122 (3) | 0.106 (2) | 0.0089 (18) | 0.0394 (18) | 0.021 (2) |
N1 | 0.0550 (12) | 0.0463 (9) | 0.0439 (9) | −0.0016 (8) | 0.0039 (8) | 0.0057 (8) |
O1 | 0.0605 (11) | 0.0502 (9) | 0.0569 (9) | 0.0054 (8) | 0.0004 (8) | 0.0074 (7) |
O2 | 0.0776 (13) | 0.0757 (10) | 0.0506 (9) | 0.0044 (8) | 0.0016 (8) | 0.0161 (8) |
O3 | 0.0663 (11) | 0.0412 (8) | 0.0618 (9) | −0.0013 (7) | 0.0006 (8) | −0.0064 (7) |
O4 | 0.0649 (13) | 0.1096 (15) | 0.0913 (14) | −0.0064 (11) | 0.0204 (11) | 0.0186 (12) |
C1—O1 | 1.399 (2) | C8—O2 | 1.233 (2) |
C1—N1 | 1.469 (2) | C8—N1 | 1.353 (3) |
C1—C2 | 1.528 (3) | C9—C10 | 1.372 (3) |
C1—H1 | 0.9800 | C9—C14 | 1.385 (3) |
C2—C7 | 1.543 (3) | C9—N1 | 1.428 (3) |
C2—C3 | 1.547 (3) | C10—C11 | 1.384 (3) |
C2—H2 | 0.9800 | C10—H10 | 0.9300 |
C3—O3 | 1.443 (2) | C11—C12 | 1.382 (4) |
C3—C4 | 1.503 (3) | C11—H11 | 0.9300 |
C3—H3 | 0.9800 | C12—C13 | 1.371 (3) |
C4—C5 | 1.345 (3) | C12—O4 | 1.380 (3) |
C4—H4 | 0.9300 | C13—C14 | 1.374 (3) |
C5—C6 | 1.498 (3) | C13—H13 | 0.9300 |
C5—H5 | 0.9300 | C14—H14 | 0.9300 |
C6—O3 | 1.439 (3) | C15—O4 | 1.360 (3) |
C6—C7 | 1.555 (3) | C15—H15A | 0.9600 |
C6—H6 | 0.9800 | C15—H15B | 0.9600 |
C7—C8 | 1.491 (3) | C15—H15C | 0.9600 |
C7—H7 | 0.9800 | O1—H1A | 0.89 (3) |
O1—C1—N1 | 111.12 (16) | C6—C7—H7 | 112.5 |
O1—C1—C2 | 115.18 (16) | O2—C8—N1 | 124.7 (2) |
N1—C1—C2 | 104.49 (16) | O2—C8—C7 | 125.3 (2) |
O1—C1—H1 | 108.6 | N1—C8—C7 | 110.02 (17) |
N1—C1—H1 | 108.6 | C10—C9—C14 | 118.8 (2) |
C2—C1—H1 | 108.6 | C10—C9—N1 | 121.1 (2) |
C1—C2—C7 | 106.36 (16) | C14—C9—N1 | 120.0 (2) |
C1—C2—C3 | 113.74 (16) | C9—C10—C11 | 120.9 (2) |
C7—C2—C3 | 100.55 (16) | C9—C10—H10 | 119.5 |
C1—C2—H2 | 111.8 | C11—C10—H10 | 119.5 |
C7—C2—H2 | 111.8 | C12—C11—C10 | 119.7 (2) |
C3—C2—H2 | 111.8 | C12—C11—H11 | 120.1 |
O3—C3—C4 | 102.03 (18) | C10—C11—H11 | 120.1 |
O3—C3—C2 | 101.04 (16) | C13—C12—O4 | 115.8 (2) |
C4—C3—C2 | 107.33 (17) | C13—C12—C11 | 119.4 (2) |
O3—C3—H3 | 114.9 | O4—C12—C11 | 124.8 (2) |
C4—C3—H3 | 114.9 | C12—C13—C14 | 120.7 (2) |
C2—C3—H3 | 114.9 | C12—C13—H13 | 119.6 |
C5—C4—C3 | 105.4 (2) | C14—C13—H13 | 119.6 |
C5—C4—H4 | 127.3 | C13—C14—C9 | 120.3 (2) |
C3—C4—H4 | 127.3 | C13—C14—H14 | 119.8 |
C4—C5—C6 | 105.1 (2) | C9—C14—H14 | 119.8 |
C4—C5—H5 | 127.5 | O4—C15—H15A | 109.5 |
C6—C5—H5 | 127.5 | O4—C15—H15B | 109.5 |
O3—C6—C5 | 102.27 (18) | H15A—C15—H15B | 109.5 |
O3—C6—C7 | 100.44 (17) | O4—C15—H15C | 109.5 |
C5—C6—C7 | 107.15 (17) | H15A—C15—H15C | 109.5 |
O3—C6—H6 | 115.1 | H15B—C15—H15C | 109.5 |
C5—C6—H6 | 115.1 | C8—N1—C9 | 124.31 (17) |
C7—C6—H6 | 115.1 | C8—N1—C1 | 113.88 (17) |
C8—C7—C2 | 105.22 (17) | C9—N1—C1 | 121.72 (17) |
C8—C7—C6 | 112.09 (17) | C1—O1—H1A | 108.2 (19) |
C2—C7—C6 | 101.45 (16) | C6—O3—C3 | 95.59 (15) |
C8—C7—H7 | 112.5 | C15—O4—C12 | 118.3 (2) |
C2—C7—H7 | 112.5 | ||
O1—C1—C2—C7 | 121.43 (18) | C9—C10—C11—C12 | −1.0 (3) |
N1—C1—C2—C7 | −0.76 (19) | C10—C11—C12—C13 | −0.4 (4) |
O1—C1—C2—C3 | −128.85 (18) | C10—C11—C12—O4 | 178.2 (2) |
N1—C1—C2—C3 | 108.96 (17) | O4—C12—C13—C14 | −178.1 (2) |
C1—C2—C3—O3 | −76.44 (19) | C11—C12—C13—C14 | 0.6 (4) |
C7—C2—C3—O3 | 36.82 (19) | C12—C13—C14—C9 | 0.4 (4) |
C1—C2—C3—C4 | 177.10 (17) | C10—C9—C14—C13 | −1.6 (3) |
C7—C2—C3—C4 | −69.6 (2) | N1—C9—C14—C13 | 178.4 (2) |
O3—C3—C4—C5 | −31.8 (2) | O2—C8—N1—C9 | −0.6 (3) |
C2—C3—C4—C5 | 74.0 (2) | C7—C8—N1—C9 | 177.79 (17) |
C3—C4—C5—C6 | −0.7 (2) | O2—C8—N1—C1 | −177.26 (19) |
C4—C5—C6—O3 | 33.1 (2) | C7—C8—N1—C1 | 1.1 (2) |
C4—C5—C6—C7 | −72.1 (2) | C10—C9—N1—C8 | 41.8 (3) |
C1—C2—C7—C8 | 1.4 (2) | C14—C9—N1—C8 | −138.2 (2) |
C3—C2—C7—C8 | −117.42 (17) | C10—C9—N1—C1 | −141.7 (2) |
C1—C2—C7—C6 | 118.28 (17) | C14—C9—N1—C1 | 38.2 (3) |
C3—C2—C7—C6 | −0.5 (2) | O1—C1—N1—C8 | −125.01 (19) |
O3—C6—C7—C8 | 75.8 (2) | C2—C1—N1—C8 | −0.2 (2) |
C5—C6—C7—C8 | −177.73 (18) | O1—C1—N1—C9 | 58.2 (2) |
O3—C6—C7—C2 | −36.0 (2) | C2—C1—N1—C9 | −176.96 (16) |
C5—C6—C7—C2 | 70.5 (2) | C5—C6—O3—C3 | −50.66 (19) |
C2—C7—C8—O2 | 176.83 (18) | C7—C6—O3—C3 | 59.65 (18) |
C6—C7—C8—O2 | 67.4 (3) | C4—C3—O3—C6 | 50.03 (19) |
C2—C7—C8—N1 | −1.5 (2) | C2—C3—O3—C6 | −60.58 (18) |
C6—C7—C8—N1 | −110.95 (19) | C13—C12—O4—C15 | −176.8 (3) |
C14—C9—C10—C11 | 1.9 (3) | C11—C12—O4—C15 | 4.6 (4) |
N1—C9—C10—C11 | −178.1 (2) |
Experimental details
Crystal data | |
Chemical formula | C15H15NO4 |
Mr | 273.28 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 11.2076 (11), 8.4910 (7), 14.1867 (15) |
β (°) | 99.457 (8) |
V (Å3) | 1331.7 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.60 × 0.32 × 0.05 |
Data collection | |
Diffractometer | Stoe IPDSII diffractometer |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.952, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9348, 2600, 1497 |
Rint | 0.070 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.105, 0.95 |
No. of reflections | 2600 |
No. of parameters | 185 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.14, −0.16 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003), WinGX (Farrugia, 1999).
D-H···A | D-H | H···A | D···A | D-H···A |
O1-H1A···O2i | 0.89 (3) | 1.85 (3) | 2.735 (2) | 172 (3) |
C1-H1···O3iii | 0.98 | 2.52 | 3.480 (2) | 165.5 |
C7-H7···Cgi | 0.98 | 2.72 | 3.676 (2) | 166 |
Cg is the centroid of the C9–C14 ring. Symmetry codes: (i) -x+1, y+1/2, -z+3/2; (iii) -x+1, -y+1, -z+1. |
The derivatives of exo-5,6-dehydronorcantharidin are of great pharmacological interest and have attracted considerable attention (Abel et al., 1996; Deng et al., 2005). Furthermore, molecules of this type containing nitrogen have become a hot topic in heterocyclic chemistry because of their antitumour, antiviral, analgesic, sedative and fungicidal activities (Salvati et al., 2005). We therefore become interested in the synthesis of the cantharidin analogue (II), with the possibility that biological activity is modified in the bicyclic imide systems. Compound (II) is generated from (I) in a single synthetic reduction by using Na(BH4). We report here the synthesis and the crystal structure of (II).
The regiochemistry of (II) was established by 1H and C NMR spectroscopy, and the diagnostic spin–spin interactions were identified with the aid of HH COSY experiments. The structure determination of (II) confirmed this connectivity and also established the exoposition with bridge H atoms of the molecule [please clarify]. The molecules of (II) are chiral, with five stereogenic centres at atoms C1, C2, C3, C6 and C7. Compound (II) crystallizes as a racemic mixture in space group P21/c. The reference molecule was selected to have S, S, R, S and R configurations at atoms C1, C2, C3, C6 and C7, respectively. Hence the racemic mixture consists of molecules whose configurations are 1S,2S,3R,6S,7R and 1R,2R,3S,6R,7S. The inter-bridgehead angles O3—C6—C7 and O3—C3—C2 of 100.44 (17) and 101.04 (16)°, respectively, are contracted with respect to the tetrahedral value, as is the C6—O3—C3 angle of 95.59 (15)°. The cyclohexane ring (C2–C7) adopts a boat conformation. The tetrahydrofuran rings (O3/C3/C2/C7/C6 and O3/C3/C4/C5/C6) have an envelope conformation with atom O3 as the flap atom, with puckering parameters (Cremer & Pople, 1975) of Q = 0.590 (2) Å, ϕ = 180.5 (2)°, Q = 0.508 (2) Å and ϕ = 359.4 (3)°, respectively. The maximum deviations of atom O3 from the planes defined by the remaining four atoms are 0.840 (1) and 0.755 (1) Å, respectively. The dihedral angle between the phenyl and imide rings is 29.28 (12)°. The methoxy substituent is approximately coplanar with the attached phenyl ring. The N—Caryl bond length is 1.428 (3) Å and is comparable to those found in previously reported structures (Trujillo-Ferrara et al., 2004; Miller et al., 2000; Ellis & Spek, 2001).
The supramolecular structure of (II) is composed of sheets generated by a combination of O—H···O, C—H···O and C—H···π hydrogen bonds (Table 1). The formation of the sheet is analyzed in terms of two different low-dimensional substructures. The first substructure is built using the O—H···O and C—H···π hydrogen bonds, where atoms O1 and C7 in the molecule at (x, y, z) act as hydrogen-bond donors, respectively, to atom O2 and the C9–C14 ring, both in the molecule at (-x + 1, y + 1/2, -z + 3/2), so forming C(6) (Bernstein et al., 1995) chains running parallel to the [010] direction (Fig. 2). The chains include only the molecules of 1S,2S,3R,6S,7R configuration. In the second substructure, atom C1 in the molecule at (x, y, z) (1S,2S,3R,6S,7R) acts as a hydrogen-bond donor to atom O3 in the molecule at (-x + 1, -y + 1, -z + 1) (1R,2R,3S,6R,7S), leading to a centrosymmetric R22(10) dimer centered at (1/2, 1/2, 1/2) (Fig. 3). The combination of these interactions generates a sheet parallel to (100). There are no direction-specific interactions between the sheets, so the supramolecular structure of the title compound is two-dimensional (Fig. 4).