Acta Cryst. (2009). E65, o2576 [ doi:10.1107/S1600536809038458 ]
There are two unique molecules in the asymmetric unit of the title compound, C17H15NO4, which are linked into chains via intermolecular N-H
O and C-HO interactions; the chains are linked via weak C-HO interactions, forming a parallel sheet structure. The molecule is approximately planar, with dihedral angles of 19.91 (4) and 11.06 (4)° between the naphthyl ring and the aminomethylene group, and between the aminomethylene unit and the planar part of the dioxane ring, respectively. The dioxane ring adopts a half-boat conformation, with the C atom between the dioxane O atoms 0.595 (8) Å out of the plane through the remaining atoms. The molecule has an intramolecular N-HO hydrogen bond which stabilizes the planar conformation.
An ethanol solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (1.44 g, 0.01 mol) with methylorthoformate (1.27 g, 0.012 mol) was heated to reflux for 2 h, then the arylamine (1.32 g, 0.01 mol) was added into the solution. The mixture was heated under reflux for another 10 h and then filtered. Single crystals were obtained from the filtrate after 2 days.
The imino H atom was located in a difference Fourier map and refined isotropically. Other H atoms were positioned geometrically with C—H = 0.93 (aromatic) or 0.96 Å (methyl), and refined using a riding model with Uĩso(H) = 1.5Ueq(C) for methyl and 1.2Ueq(C) for the others.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
![[Figure 1]](./bv2127fig1thm.gif)
| Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. |
| C17H15NO4 | Z = 4 |
| Mr = 297.30 | F(000) = 624 |
| Triclinic, P1 | Dx = 1.349 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 10.6204 (17) Å | Cell parameters from 2937 reflections |
| b = 11.8220 (19) Å | θ = 2.5–27.5° |
| c = 12.0143 (19) Å | µ = 0.10 mm−1 |
| α = 78.237 (2)° | T = 153 K |
| β = 86.786 (2)° | Block, colourless |
| γ = 82.469 (2)° | 0.25 × 0.22 × 0.20 mm |
| V = 1463.4 (4) Å3 |
| Bruker SMART CCD area-detector diffractometer | 4313 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.024 |
| graphite | θmax = 27.6°, θmin = 2.5° |
| φ and ω scans | h = −10→13 |
| 9205 measured reflections | k = −15→14 |
| 6490 independent reflections | l = −15→14 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: mixed |
| R[F2 > 2σ(F2)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.0403P)2 + 0.2303P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.11 | (Δ/σ)max < 0.001 |
| 6490 reflections | Δρmax = 0.23 e Å−3 |
| 410 parameters | Δρmin = −0.19 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.045 (2) |
| C17H15NO4 | γ = 82.469 (2)° |
| Mr = 297.30 | V = 1463.4 (4) Å3 |
| Triclinic, P1 | Z = 4 |
| a = 10.6204 (17) Å | Mo Kα radiation |
| b = 11.8220 (19) Å | µ = 0.10 mm−1 |
| c = 12.0143 (19) Å | T = 153 K |
| α = 78.237 (2)° | 0.25 × 0.22 × 0.20 mm |
| β = 86.786 (2)° |
| Bruker SMART CCD area-detector diffractometer | 4313 reflections with I > 2σ(I) |
| 9205 measured reflections | Rint = 0.024 |
| 6490 independent reflections | θmax = 27.6° |
| R[F2 > 2σ(F2)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.127 | Δρmax = 0.23 e Å−3 |
| S = 1.11 | Δρmin = −0.19 e Å−3 |
| 6490 reflections | Absolute structure: ? |
| 410 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | 0.09234 (11) | 0.24925 (9) | 0.63633 (8) | 0.0467 (3) | |
| O2 | −0.06511 (10) | 0.17438 (10) | 0.55278 (9) | 0.0477 (3) | |
| O3 | 0.17092 (13) | 0.40987 (10) | 0.55022 (9) | 0.0590 (4) | |
| O4 | −0.13735 (13) | 0.25516 (13) | 0.38302 (11) | 0.0739 (4) | |
| N1 | 0.13306 (14) | 0.48532 (12) | 0.31953 (12) | 0.0455 (3) | |
| H1 | 0.1759 (19) | 0.4990 (18) | 0.3788 (17) | 0.078 (7)* | |
| C1 | 0.01090 (19) | 0.07785 (16) | 0.73214 (15) | 0.0578 (5) | |
| H1A | −0.0588 | 0.1241 | 0.7658 | 0.087* | |
| H1B | 0.0839 | 0.0615 | 0.7819 | 0.087* | |
| H1C | −0.0170 | 0.0044 | 0.7235 | 0.087* | |
| C2 | 0.15032 (16) | 0.07683 (15) | 0.55656 (15) | 0.0534 (4) | |
| H2A | 0.1202 | 0.0048 | 0.5463 | 0.080* | |
| H2B | 0.2271 | 0.0577 | 0.6016 | 0.080* | |
| H2C | 0.1698 | 0.1239 | 0.4820 | 0.080* | |
| C3 | 0.04856 (15) | 0.14458 (13) | 0.61769 (13) | 0.0406 (4) | |
| C4 | 0.10548 (16) | 0.33504 (13) | 0.54327 (13) | 0.0413 (4) | |
| C5 | 0.03603 (15) | 0.33192 (13) | 0.44535 (13) | 0.0413 (4) | |
| C6 | −0.06033 (16) | 0.25392 (15) | 0.45320 (14) | 0.0474 (4) | |
| C7 | 0.05448 (15) | 0.40537 (14) | 0.34294 (13) | 0.0450 (4) | |
| H7 | 0.0050 | 0.3977 | 0.2820 | 0.054* | |
| C8 | 0.15665 (15) | 0.54980 (13) | 0.20834 (12) | 0.0412 (4) | |
| C9 | 0.19882 (15) | 0.65634 (14) | 0.19600 (13) | 0.0425 (4) | |
| H9 | 0.2116 | 0.6864 | 0.2615 | 0.051* | |
| C10 | 0.22353 (14) | 0.72218 (13) | 0.08622 (13) | 0.0407 (4) | |
| C11 | 0.26546 (18) | 0.83343 (16) | 0.06954 (15) | 0.0562 (5) | |
| H11 | 0.2766 | 0.8665 | 0.1335 | 0.067* | |
| C12 | 0.2901 (2) | 0.89383 (17) | −0.03759 (17) | 0.0669 (6) | |
| H12 | 0.3186 | 0.9682 | −0.0474 | 0.080* | |
| C13 | 0.27356 (19) | 0.84666 (17) | −0.13264 (16) | 0.0635 (5) | |
| H13 | 0.2916 | 0.8891 | −0.2066 | 0.076* | |
| C14 | 0.23192 (17) | 0.74096 (17) | −0.12038 (14) | 0.0543 (5) | |
| H14 | 0.2207 | 0.7102 | −0.1858 | 0.065* | |
| C15 | 0.20497 (15) | 0.67593 (14) | −0.01052 (13) | 0.0428 (4) | |
| C16 | 0.16170 (17) | 0.56607 (15) | 0.00616 (14) | 0.0525 (4) | |
| H16 | 0.1483 | 0.5345 | −0.0582 | 0.063* | |
| C17 | 0.13853 (17) | 0.50381 (15) | 0.11220 (14) | 0.0518 (4) | |
| H17 | 0.1102 | 0.4294 | 0.1212 | 0.062* | |
| O5 | 0.42844 (11) | 0.73498 (10) | 0.35805 (9) | 0.0496 (3) | |
| O6 | 0.57288 (11) | 0.81921 (10) | 0.44864 (10) | 0.0524 (3) | |
| O7 | 0.33468 (12) | 0.58478 (10) | 0.44833 (10) | 0.0573 (3) | |
| O8 | 0.62505 (15) | 0.75181 (14) | 0.62628 (12) | 0.0866 (5) | |
| N2 | 0.37240 (13) | 0.50869 (12) | 0.68054 (11) | 0.0445 (3) | |
| H2 | 0.3243 (19) | 0.4993 (18) | 0.6238 (17) | 0.078 (7)* | |
| C18 | 0.5313 (2) | 0.89190 (17) | 0.25626 (15) | 0.0648 (5) | |
| H18A | 0.5608 | 0.9662 | 0.2598 | 0.097* | |
| H18B | 0.4678 | 0.9046 | 0.1974 | 0.097* | |
| H18C | 0.6035 | 0.8375 | 0.2377 | 0.097* | |
| C19 | 0.36396 (17) | 0.92034 (15) | 0.40890 (17) | 0.0641 (5) | |
| H19A | 0.3331 | 0.8835 | 0.4843 | 0.096* | |
| H19B | 0.2951 | 0.9340 | 0.3550 | 0.096* | |
| H19C | 0.3927 | 0.9947 | 0.4131 | 0.096* | |
| C20 | 0.47273 (15) | 0.84181 (14) | 0.36956 (13) | 0.0427 (4) | |
| C21 | 0.40282 (15) | 0.65788 (13) | 0.45482 (13) | 0.0409 (4) | |
| C22 | 0.46411 (15) | 0.66640 (14) | 0.55547 (13) | 0.0423 (4) | |
| C23 | 0.55744 (17) | 0.74667 (16) | 0.55030 (15) | 0.0527 (4) | |
| C24 | 0.44707 (16) | 0.59171 (14) | 0.65771 (14) | 0.0469 (4) | |
| H24 | 0.4948 | 0.6011 | 0.7191 | 0.056* | |
| C25 | 0.36078 (15) | 0.43352 (13) | 0.78831 (12) | 0.0401 (4) | |
| C26 | 0.25699 (15) | 0.37528 (13) | 0.81217 (12) | 0.0401 (4) | |
| H26 | 0.1945 | 0.3850 | 0.7563 | 0.048* | |
| C27 | 0.24066 (15) | 0.30061 (13) | 0.91865 (12) | 0.0393 (4) | |
| C28 | 0.13167 (17) | 0.24240 (15) | 0.94677 (15) | 0.0519 (4) | |
| H28 | 0.0682 | 0.2506 | 0.8920 | 0.062* | |
| C29 | 0.11669 (19) | 0.17443 (17) | 1.05196 (16) | 0.0656 (5) | |
| H29 | 0.0429 | 0.1360 | 1.0698 | 0.079* | |
| C30 | 0.2093 (2) | 0.16097 (18) | 1.13367 (16) | 0.0681 (6) | |
| H30 | 0.1974 | 0.1139 | 1.2067 | 0.082* | |
| C31 | 0.31577 (19) | 0.21456 (16) | 1.10953 (15) | 0.0599 (5) | |
| H31 | 0.3782 | 0.2040 | 1.1656 | 0.072* | |
| C32 | 0.33477 (15) | 0.28624 (14) | 1.00126 (13) | 0.0443 (4) | |
| C33 | 0.44196 (16) | 0.34644 (16) | 0.97260 (15) | 0.0554 (5) | |
| H33 | 0.5062 | 0.3371 | 1.0268 | 0.066* | |
| C34 | 0.45594 (16) | 0.41743 (16) | 0.86962 (15) | 0.0538 (5) | |
| H34 | 0.5296 | 0.4562 | 0.8523 | 0.065* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0684 (8) | 0.0379 (6) | 0.0360 (6) | −0.0205 (5) | −0.0011 (5) | −0.0034 (5) |
| O2 | 0.0396 (6) | 0.0470 (7) | 0.0538 (7) | −0.0157 (5) | −0.0014 (5) | 0.0026 (5) |
| O3 | 0.0873 (9) | 0.0488 (7) | 0.0466 (7) | −0.0372 (7) | −0.0040 (6) | −0.0040 (6) |
| O4 | 0.0644 (9) | 0.0939 (11) | 0.0631 (8) | −0.0350 (8) | −0.0208 (7) | 0.0064 (8) |
| N1 | 0.0535 (9) | 0.0405 (8) | 0.0391 (8) | −0.0105 (6) | 0.0003 (6) | 0.0024 (6) |
| C1 | 0.0670 (12) | 0.0452 (10) | 0.0570 (11) | −0.0183 (9) | 0.0054 (9) | 0.0046 (8) |
| C2 | 0.0477 (10) | 0.0421 (10) | 0.0709 (12) | −0.0088 (8) | 0.0029 (9) | −0.0115 (9) |
| C3 | 0.0421 (9) | 0.0341 (8) | 0.0457 (9) | −0.0134 (7) | −0.0018 (7) | −0.0024 (7) |
| C4 | 0.0536 (10) | 0.0342 (8) | 0.0362 (8) | −0.0135 (7) | 0.0037 (7) | −0.0036 (6) |
| C5 | 0.0444 (9) | 0.0373 (8) | 0.0403 (8) | −0.0087 (7) | −0.0002 (7) | −0.0011 (7) |
| C6 | 0.0444 (9) | 0.0512 (10) | 0.0446 (9) | −0.0110 (8) | −0.0030 (7) | −0.0012 (8) |
| C7 | 0.0450 (9) | 0.0456 (9) | 0.0417 (9) | −0.0063 (7) | −0.0036 (7) | −0.0012 (7) |
| C8 | 0.0452 (9) | 0.0379 (9) | 0.0361 (8) | −0.0043 (7) | 0.0025 (7) | 0.0010 (7) |
| C9 | 0.0476 (9) | 0.0441 (9) | 0.0353 (8) | −0.0095 (7) | −0.0031 (7) | −0.0037 (7) |
| C10 | 0.0401 (9) | 0.0402 (9) | 0.0388 (8) | −0.0062 (7) | −0.0012 (6) | −0.0002 (7) |
| C11 | 0.0656 (12) | 0.0491 (10) | 0.0535 (10) | −0.0188 (9) | 0.0028 (9) | −0.0034 (8) |
| C12 | 0.0770 (14) | 0.0516 (11) | 0.0663 (13) | −0.0209 (10) | 0.0066 (11) | 0.0077 (10) |
| C13 | 0.0665 (13) | 0.0625 (12) | 0.0494 (11) | −0.0103 (10) | 0.0036 (9) | 0.0175 (9) |
| C14 | 0.0540 (11) | 0.0664 (12) | 0.0374 (9) | −0.0041 (9) | 0.0004 (8) | −0.0011 (8) |
| C15 | 0.0413 (9) | 0.0462 (9) | 0.0376 (8) | −0.0031 (7) | 0.0001 (7) | −0.0022 (7) |
| C16 | 0.0683 (12) | 0.0515 (10) | 0.0402 (9) | −0.0112 (9) | 0.0065 (8) | −0.0147 (8) |
| C17 | 0.0689 (12) | 0.0381 (9) | 0.0501 (10) | −0.0131 (8) | 0.0101 (8) | −0.0118 (8) |
| O5 | 0.0693 (8) | 0.0437 (7) | 0.0390 (6) | −0.0249 (6) | 0.0039 (5) | −0.0060 (5) |
| O6 | 0.0456 (7) | 0.0548 (7) | 0.0549 (7) | −0.0212 (6) | −0.0028 (5) | 0.0036 (6) |
| O7 | 0.0753 (9) | 0.0505 (7) | 0.0513 (7) | −0.0328 (7) | −0.0010 (6) | −0.0066 (6) |
| O8 | 0.0945 (11) | 0.1021 (12) | 0.0665 (9) | −0.0550 (10) | −0.0292 (8) | 0.0102 (8) |
| N2 | 0.0478 (8) | 0.0442 (8) | 0.0391 (8) | −0.0097 (6) | 0.0028 (6) | −0.0011 (6) |
| C18 | 0.0769 (13) | 0.0625 (12) | 0.0536 (11) | −0.0314 (11) | 0.0089 (10) | 0.0032 (9) |
| C19 | 0.0556 (11) | 0.0437 (10) | 0.0898 (15) | −0.0043 (9) | 0.0040 (10) | −0.0085 (10) |
| C20 | 0.0454 (9) | 0.0363 (8) | 0.0474 (9) | −0.0150 (7) | −0.0019 (7) | −0.0039 (7) |
| C21 | 0.0474 (9) | 0.0360 (8) | 0.0398 (8) | −0.0116 (7) | 0.0072 (7) | −0.0068 (7) |
| C22 | 0.0436 (9) | 0.0407 (9) | 0.0415 (9) | −0.0106 (7) | 0.0021 (7) | −0.0036 (7) |
| C23 | 0.0522 (10) | 0.0569 (11) | 0.0488 (10) | −0.0182 (9) | −0.0052 (8) | −0.0019 (8) |
| C24 | 0.0478 (10) | 0.0474 (10) | 0.0448 (9) | −0.0101 (8) | 0.0012 (7) | −0.0052 (8) |
| C25 | 0.0424 (9) | 0.0389 (8) | 0.0361 (8) | −0.0035 (7) | 0.0032 (7) | −0.0030 (7) |
| C26 | 0.0450 (9) | 0.0404 (9) | 0.0345 (8) | −0.0057 (7) | −0.0034 (6) | −0.0057 (7) |
| C27 | 0.0422 (9) | 0.0370 (8) | 0.0376 (8) | −0.0045 (7) | −0.0004 (7) | −0.0052 (7) |
| C28 | 0.0501 (10) | 0.0479 (10) | 0.0551 (10) | −0.0120 (8) | −0.0050 (8) | 0.0003 (8) |
| C29 | 0.0589 (12) | 0.0595 (12) | 0.0696 (13) | −0.0179 (10) | 0.0024 (10) | 0.0133 (10) |
| C30 | 0.0727 (13) | 0.0635 (13) | 0.0547 (11) | −0.0132 (10) | 0.0011 (10) | 0.0217 (9) |
| C31 | 0.0640 (12) | 0.0604 (12) | 0.0470 (10) | −0.0051 (10) | −0.0118 (9) | 0.0102 (9) |
| C32 | 0.0460 (9) | 0.0405 (9) | 0.0419 (9) | −0.0017 (7) | −0.0043 (7) | 0.0007 (7) |
| C33 | 0.0463 (10) | 0.0602 (11) | 0.0542 (10) | −0.0065 (8) | −0.0162 (8) | 0.0056 (9) |
| C34 | 0.0390 (9) | 0.0572 (11) | 0.0594 (11) | −0.0111 (8) | −0.0048 (8) | 0.0063 (9) |
| O1—C4 | 1.3621 (17) | O5—C21 | 1.3616 (17) |
| O1—C3 | 1.4399 (17) | O5—C20 | 1.4386 (18) |
| O2—C6 | 1.3657 (18) | O6—C23 | 1.3570 (19) |
| O2—C3 | 1.4393 (18) | O6—C20 | 1.4286 (19) |
| O3—C4 | 1.2126 (18) | O7—C21 | 1.2143 (18) |
| O4—C6 | 1.2039 (19) | O8—C23 | 1.208 (2) |
| N1—C7 | 1.319 (2) | N2—C24 | 1.318 (2) |
| N1—C8 | 1.4232 (18) | N2—C25 | 1.4223 (19) |
| N1—H1 | 0.92 (2) | N2—H2 | 0.91 (2) |
| C1—C3 | 1.501 (2) | C18—C20 | 1.504 (2) |
| C1—H1A | 0.9800 | C18—H18A | 0.9800 |
| C1—H1B | 0.9800 | C18—H18B | 0.9800 |
| C1—H1C | 0.9800 | C18—H18C | 0.9800 |
| C2—C3 | 1.508 (2) | C19—C20 | 1.502 (2) |
| C2—H2A | 0.9800 | C19—H19A | 0.9800 |
| C2—H2B | 0.9800 | C19—H19B | 0.9800 |
| C2—H2C | 0.9800 | C19—H19C | 0.9800 |
| C4—C5 | 1.432 (2) | C21—C22 | 1.432 (2) |
| C5—C7 | 1.374 (2) | C22—C24 | 1.377 (2) |
| C5—C6 | 1.452 (2) | C22—C23 | 1.450 (2) |
| C7—H7 | 0.9500 | C24—H24 | 0.9500 |
| C8—C9 | 1.369 (2) | C25—C26 | 1.362 (2) |
| C8—C17 | 1.405 (2) | C25—C34 | 1.413 (2) |
| C9—C10 | 1.418 (2) | C26—C27 | 1.414 (2) |
| C9—H9 | 0.9500 | C26—H26 | 0.9500 |
| C10—C15 | 1.415 (2) | C27—C28 | 1.413 (2) |
| C10—C11 | 1.416 (2) | C27—C32 | 1.418 (2) |
| C11—C12 | 1.368 (2) | C28—C29 | 1.366 (2) |
| C11—H11 | 0.9500 | C28—H28 | 0.9500 |
| C12—C13 | 1.398 (3) | C29—C30 | 1.400 (3) |
| C12—H12 | 0.9500 | C29—H29 | 0.9500 |
| C13—C14 | 1.357 (3) | C30—C31 | 1.357 (3) |
| C13—H13 | 0.9500 | C30—H30 | 0.9500 |
| C14—C15 | 1.420 (2) | C31—C32 | 1.420 (2) |
| C14—H14 | 0.9500 | C31—H31 | 0.9500 |
| C15—C16 | 1.406 (2) | C32—C33 | 1.410 (2) |
| C16—C17 | 1.362 (2) | C33—C34 | 1.359 (2) |
| C16—H16 | 0.9500 | C33—H33 | 0.9500 |
| C17—H17 | 0.9500 | C34—H34 | 0.9500 |
| C4—O1—C3 | 117.01 (11) | C21—O5—C20 | 117.93 (12) |
| C6—O2—C3 | 117.24 (12) | C23—O6—C20 | 118.76 (12) |
| C7—N1—C8 | 124.07 (15) | C24—N2—C25 | 124.62 (15) |
| C7—N1—H1 | 117.5 (13) | C24—N2—H2 | 117.8 (13) |
| C8—N1—H1 | 118.4 (13) | C25—N2—H2 | 117.6 (13) |
| C3—C1—H1A | 109.5 | C20—C18—H18A | 109.5 |
| C3—C1—H1B | 109.5 | C20—C18—H18B | 109.5 |
| H1A—C1—H1B | 109.5 | H18A—C18—H18B | 109.5 |
| C3—C1—H1C | 109.5 | C20—C18—H18C | 109.5 |
| H1A—C1—H1C | 109.5 | H18A—C18—H18C | 109.5 |
| H1B—C1—H1C | 109.5 | H18B—C18—H18C | 109.5 |
| C3—C2—H2A | 109.5 | C20—C19—H19A | 109.5 |
| C3—C2—H2B | 109.5 | C20—C19—H19B | 109.5 |
| H2A—C2—H2B | 109.5 | H19A—C19—H19B | 109.5 |
| C3—C2—H2C | 109.5 | C20—C19—H19C | 109.5 |
| H2A—C2—H2C | 109.5 | H19A—C19—H19C | 109.5 |
| H2B—C2—H2C | 109.5 | H19B—C19—H19C | 109.5 |
| O1—C3—O2 | 109.46 (12) | O6—C20—O5 | 110.64 (12) |
| O1—C3—C1 | 106.82 (13) | O6—C20—C19 | 110.09 (14) |
| O2—C3—C1 | 106.47 (13) | O5—C20—C19 | 109.23 (13) |
| O1—C3—C2 | 110.33 (12) | O6—C20—C18 | 105.89 (13) |
| O2—C3—C2 | 110.52 (13) | O5—C20—C18 | 106.83 (13) |
| C1—C3—C2 | 113.07 (14) | C19—C20—C18 | 114.08 (15) |
| O3—C4—O1 | 118.26 (14) | O7—C21—O5 | 117.95 (14) |
| O3—C4—C5 | 124.93 (14) | O7—C21—C22 | 125.19 (14) |
| O1—C4—C5 | 116.77 (13) | O5—C21—C22 | 116.78 (13) |
| C7—C5—C4 | 121.39 (14) | C24—C22—C21 | 121.87 (15) |
| C7—C5—C6 | 118.04 (15) | C24—C22—C23 | 117.21 (15) |
| C4—C5—C6 | 120.52 (14) | C21—C22—C23 | 120.61 (14) |
| O4—C6—O2 | 117.83 (15) | O8—C23—O6 | 117.59 (16) |
| O4—C6—C5 | 126.67 (15) | O8—C23—C22 | 126.17 (16) |
| O2—C6—C5 | 115.46 (14) | O6—C23—C22 | 116.19 (15) |
| N1—C7—C5 | 127.43 (16) | N2—C24—C22 | 127.68 (16) |
| N1—C7—H7 | 116.3 | N2—C24—H24 | 116.2 |
| C5—C7—H7 | 116.3 | C22—C24—H24 | 116.2 |
| C9—C8—C17 | 120.32 (14) | C26—C25—C34 | 119.89 (14) |
| C9—C8—N1 | 119.35 (14) | C26—C25—N2 | 119.13 (14) |
| C17—C8—N1 | 120.33 (14) | C34—C25—N2 | 120.96 (14) |
| C8—C9—C10 | 120.49 (14) | C25—C26—C27 | 121.14 (14) |
| C8—C9—H9 | 119.8 | C25—C26—H26 | 119.4 |
| C10—C9—H9 | 119.8 | C27—C26—H26 | 119.4 |
| C15—C10—C11 | 118.51 (14) | C28—C27—C26 | 122.14 (14) |
| C15—C10—C9 | 119.14 (14) | C28—C27—C32 | 118.80 (14) |
| C11—C10—C9 | 122.35 (15) | C26—C27—C32 | 119.04 (14) |
| C12—C11—C10 | 120.78 (17) | C29—C28—C27 | 120.60 (17) |
| C12—C11—H11 | 119.6 | C29—C28—H28 | 119.7 |
| C10—C11—H11 | 119.6 | C27—C28—H28 | 119.7 |
| C11—C12—C13 | 120.34 (18) | C28—C29—C30 | 120.53 (17) |
| C11—C12—H12 | 119.8 | C28—C29—H29 | 119.7 |
| C13—C12—H12 | 119.8 | C30—C29—H29 | 119.7 |
| C14—C13—C12 | 120.71 (16) | C31—C30—C29 | 120.61 (17) |
| C14—C13—H13 | 119.6 | C31—C30—H30 | 119.7 |
| C12—C13—H13 | 119.6 | C29—C30—H30 | 119.7 |
| C13—C14—C15 | 120.52 (17) | C30—C31—C32 | 120.60 (17) |
| C13—C14—H14 | 119.7 | C30—C31—H31 | 119.7 |
| C15—C14—H14 | 119.7 | C32—C31—H31 | 119.7 |
| C16—C15—C10 | 118.43 (14) | C33—C32—C27 | 118.13 (14) |
| C16—C15—C14 | 122.44 (15) | C33—C32—C31 | 122.99 (16) |
| C10—C15—C14 | 119.13 (15) | C27—C32—C31 | 118.86 (15) |
| C17—C16—C15 | 121.73 (15) | C34—C33—C32 | 121.85 (16) |
| C17—C16—H16 | 119.1 | C34—C33—H33 | 119.1 |
| C15—C16—H16 | 119.1 | C32—C33—H33 | 119.1 |
| C16—C17—C8 | 119.88 (15) | C33—C34—C25 | 119.93 (15) |
| C16—C17—H17 | 120.1 | C33—C34—H34 | 120.0 |
| C8—C17—H17 | 120.1 | C25—C34—H34 | 120.0 |
| C4—O1—C3—O2 | −51.22 (17) | C23—O6—C20—O5 | −47.53 (19) |
| C4—O1—C3—C1 | −166.12 (14) | C23—O6—C20—C19 | 73.30 (18) |
| C4—O1—C3—C2 | 70.61 (17) | C23—O6—C20—C18 | −162.94 (15) |
| C6—O2—C3—O1 | 52.86 (17) | C21—O5—C20—O6 | 47.95 (18) |
| C6—O2—C3—C1 | 167.99 (14) | C21—O5—C20—C19 | −73.39 (18) |
| C6—O2—C3—C2 | −68.85 (17) | C21—O5—C20—C18 | 162.76 (14) |
| C3—O1—C4—O3 | −161.61 (15) | C20—O5—C21—O7 | 160.40 (14) |
| C3—O1—C4—C5 | 20.7 (2) | C20—O5—C21—C22 | −22.6 (2) |
| O3—C4—C5—C7 | 10.6 (3) | O7—C21—C22—C24 | −2.1 (3) |
| O1—C4—C5—C7 | −171.89 (14) | O5—C21—C22—C24 | −178.83 (14) |
| O3—C4—C5—C6 | −166.65 (17) | O7—C21—C22—C23 | 171.31 (17) |
| O1—C4—C5—C6 | 10.8 (2) | O5—C21—C22—C23 | −5.5 (2) |
| C3—O2—C6—O4 | 158.74 (16) | C20—O6—C23—O8 | −161.02 (17) |
| C3—O2—C6—C5 | −23.5 (2) | C20—O6—C23—C22 | 21.5 (2) |
| C7—C5—C6—O4 | −9.3 (3) | C24—C22—C23—O8 | 2.6 (3) |
| C4—C5—C6—O4 | 168.11 (18) | C21—C22—C23—O8 | −171.02 (19) |
| C7—C5—C6—O2 | 173.17 (14) | C24—C22—C23—O6 | 179.83 (15) |
| C4—C5—C6—O2 | −9.4 (2) | C21—C22—C23—O6 | 6.2 (2) |
| C8—N1—C7—C5 | 173.10 (16) | C25—N2—C24—C22 | 179.14 (16) |
| C4—C5—C7—N1 | −0.2 (3) | C21—C22—C24—N2 | −3.1 (3) |
| C6—C5—C7—N1 | 177.14 (16) | C23—C22—C24—N2 | −176.69 (16) |
| C7—N1—C8—C9 | 155.71 (16) | C24—N2—C25—C26 | 161.00 (16) |
| C7—N1—C8—C17 | −25.2 (2) | C24—N2—C25—C34 | −19.9 (2) |
| C17—C8—C9—C10 | 0.6 (2) | C34—C25—C26—C27 | 1.6 (2) |
| N1—C8—C9—C10 | 179.75 (14) | N2—C25—C26—C27 | −179.29 (14) |
| C8—C9—C10—C15 | −0.5 (2) | C25—C26—C27—C28 | 177.77 (16) |
| C8—C9—C10—C11 | 179.06 (16) | C25—C26—C27—C32 | −0.3 (2) |
| C15—C10—C11—C12 | −1.4 (3) | C26—C27—C28—C29 | −177.48 (17) |
| C9—C10—C11—C12 | 179.07 (17) | C32—C27—C28—C29 | 0.6 (3) |
| C10—C11—C12—C13 | 0.3 (3) | C27—C28—C29—C30 | −0.2 (3) |
| C11—C12—C13—C14 | 0.5 (3) | C28—C29—C30—C31 | −0.4 (3) |
| C12—C13—C14—C15 | −0.3 (3) | C29—C30—C31—C32 | 0.6 (3) |
| C11—C10—C15—C16 | −179.17 (16) | C28—C27—C32—C33 | −178.95 (16) |
| C9—C10—C15—C16 | 0.4 (2) | C26—C27—C32—C33 | −0.8 (2) |
| C11—C10—C15—C14 | 1.6 (2) | C28—C27—C32—C31 | −0.4 (2) |
| C9—C10—C15—C14 | −178.87 (15) | C26—C27—C32—C31 | 177.72 (15) |
| C13—C14—C15—C16 | −179.98 (17) | C30—C31—C32—C33 | 178.27 (19) |
| C13—C14—C15—C10 | −0.7 (3) | C30—C31—C32—C27 | −0.2 (3) |
| C10—C15—C16—C17 | −0.5 (3) | C27—C32—C33—C34 | 0.6 (3) |
| C14—C15—C16—C17 | 178.76 (17) | C31—C32—C33—C34 | −177.87 (18) |
| C15—C16—C17—C8 | 0.6 (3) | C32—C33—C34—C25 | 0.7 (3) |
| C9—C8—C17—C16 | −0.7 (3) | C26—C25—C34—C33 | −1.9 (3) |
| N1—C8—C17—C16 | −179.82 (16) | N2—C25—C34—C33 | 179.09 (16) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O3 | 0.92 (2) | 2.11 (2) | 2.7681 (18) | 127.2 (16) |
| N1—H1···O7 | 0.92 (2) | 2.35 (2) | 3.184 (2) | 150.9 (17) |
| N2—H2···O7 | 0.91 (2) | 2.15 (2) | 2.7858 (18) | 126.7 (17) |
| N2—H2···O3 | 0.91 (2) | 2.36 (2) | 3.1893 (19) | 152.9 (17) |
| C7—H7···O4 | 0.95 | 2.50 | 2.833 (2) | 101 |
| C14—H14···O4i | 0.95 | 2.51 | 3.354 (2) | 148 |
| C24—H24···O8 | 0.95 | 2.45 | 2.804 (2) | 102 |
| C26—H26···O3 | 0.95 | 2.46 | 3.2569 (19) | 142 |
| Symmetry codes: (i) −x, −y+1, −z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O3 | 0.92 (2) | 2.11 (2) | 2.7681 (18) | 127.2 (16) |
| N1—H1···O7 | 0.92 (2) | 2.35 (2) | 3.184 (2) | 150.9 (17) |
| N2—H2···O7 | 0.91 (2) | 2.15 (2) | 2.7858 (18) | 126.7 (17) |
| N2—H2···O3 | 0.91 (2) | 2.36 (2) | 3.1893 (19) | 152.9 (17) |
| C7—H7···O4 | 0.95 | 2.50 | 2.833 (2) | 101 |
| C14—H14···O4i | 0.95 | 2.51 | 3.354 (2) | 148 |
| C24—H24···O8 | 0.95 | 2.45 | 2.804 (2) | 102 |
| C26—H26···O3 | 0.95 | 2.46 | 3.2569 (19) | 142 |
| Symmetry codes: (i) −x, −y+1, −z. |
This work was supported by the National Natural Science Foundation of China (30901743)
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5-Arylaminomethylene-2,2-dimethyl-1,3-dioxane-4,6-diones are key intermediates and can be used to synthesize 4(1H)quinolone derivatives by thermolysis (Cassis et al., 1985) which can be used as precursors for anticancer agents, anti-malarial agents and reversible (H+/K+) ATPase inhibitors (Ruchelman et al.,2003). The molecule (Fig. 1) is approximately planar with dihedral angles of 19.91 (4)° and 11.06 (4)° between the benzyl ring and the aminomethylene group, and between the aminomethylene unit and the planar part of the dioxane ring, respectively. In addition, the dioxane ring of the title compound adopts a half-boat conformation, in which the C atom between the dioxane oxygen atoms is -0.595 (8) Å out-of-plane. The intramolecular N—H···O hydrogen bond (Table 1) is stabilizing the planar conformation in the molecule.