Acta Cryst. (2009). E65, o558 [ doi:10.1107/S1600536809005418 ]
In the molecule of the title compound, C17H24N2O6, the dihedral angle between the four coplanar atoms of the piperidine ring and the benzene ring is 39.2 (1)°.
A solution of methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoate (0.013 mol), potassium carbonate (0.052mol), sodium iodide (0.026mol) in acetonitrile (33 mL) was stirred for 5-10 min at room temperature. Piperidine (0.040mol) was added and this mixture heated to reflux for 3 h. Reaction progress was monitored by TLC. Solid material was removed by filtration and washed with acetone. The combined filtrates were evaporated and the dark product obtained dissolved in dichloromethane (30 ml) and extracted with water (4 × 10 ml). The organic phase was dried (Na2SO4), decolorized (charcoal), filtered and evaporated to afford the product (yield; 71.2%,) as an amber oil. Yellow blocks of (I) were obtained by slow evaporation of an methanol solution.
H atoms were positioned geometrically, with C-H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: PLATON (Spek, 2009).
![[Figure 1]](./hb2910fig1thm.gif)
| Fig. 1. The molecular structure of (I) showing 50% displacement ellipsoids for the non-hydrogen atoms. |
| C17H24N2O6 | F(000) = 752 |
| Mr = 352.38 | Dx = 1.301 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 25 reflections |
| a = 10.073 (2) Å | θ = 10–13° |
| b = 11.140 (2) Å | µ = 0.10 mm−1 |
| c = 16.161 (3) Å | T = 293 K |
| β = 97.23 (3)° | Block, yellow |
| V = 1799.1 (6) Å3 | 0.30 × 0.20 × 0.20 mm |
| Z = 4 |
| Enraf–Nonius CAD-4 diffractometer | 1950 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.042 |
| graphite | θmax = 25.3°, θmin = 2.2° |
| ω/2θ scans | h = 0→12 |
| Absorption correction: ψ scan (North et al., 1968) | k = 0→13 |
| Tmin = 0.971, Tmax = 0.981 | l = −19→19 |
| 3458 measured reflections | 3 standard reflections every 200 reflections |
| 3262 independent reflections | intensity decay: 1% |
| 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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.175 | H-atom parameters constrained |
| S = 1.01 | w = 1/[σ2(Fo2) + (0.06P)2 + 2.6P] where P = (Fo2 + 2Fc2)/3 |
| 3262 reflections | (Δ/σ)max < 0.001 |
| 226 parameters | Δρmax = 0.25 e Å−3 |
| 0 restraints | Δρmin = −0.29 e Å−3 |
| C17H24N2O6 | V = 1799.1 (6) Å3 |
| Mr = 352.38 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 10.073 (2) Å | µ = 0.10 mm−1 |
| b = 11.140 (2) Å | T = 293 K |
| c = 16.161 (3) Å | 0.30 × 0.20 × 0.20 mm |
| β = 97.23 (3)° |
| Enraf–Nonius CAD-4 diffractometer | 1950 reflections with I > 2σ(I) |
| Absorption correction: ψ scan (North et al., 1968) | Rint = 0.042 |
| Tmin = 0.971, Tmax = 0.981 | θmax = 25.3° |
| 3458 measured reflections | 3 standard reflections every 200 reflections |
| 3262 independent reflections | intensity decay: 1% |
| R[F2 > 2σ(F2)] = 0.068 | H-atom parameters constrained |
| wR(F2) = 0.175 | Δρmax = 0.25 e Å−3 |
| S = 1.01 | Δρmin = −0.29 e Å−3 |
| 3262 reflections | Absolute structure: ? |
| 226 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | 1.0523 (2) | 0.3714 (2) | 0.40317 (15) | 0.0487 (7) | |
| O2 | 1.0082 (3) | 0.1757 (2) | 0.38640 (16) | 0.0563 (7) | |
| O3 | 0.7178 (3) | 0.5462 (3) | 0.32890 (18) | 0.0746 (10) | |
| O4 | 0.7681 (3) | 0.3835 (3) | 0.39767 (17) | 0.0627 (8) | |
| O5 | 0.8037 (2) | 0.4291 (2) | 0.03763 (13) | 0.0404 (6) | |
| O6 | 0.9697 (2) | 0.2550 (2) | 0.05972 (14) | 0.0408 (6) | |
| N1 | 0.7693 (3) | 0.4455 (3) | 0.33404 (18) | 0.0445 (8) | |
| N2 | 0.6436 (2) | 0.7187 (2) | −0.17424 (16) | 0.0314 (6) | |
| C1 | 1.1303 (4) | 0.3499 (4) | 0.4829 (2) | 0.0633 (12) | |
| H1A | 1.1646 | 0.4247 | 0.5061 | 0.095* | |
| H1B | 1.2035 | 0.2973 | 0.4756 | 0.095* | |
| H1C | 1.0748 | 0.3134 | 0.5199 | 0.095* | |
| C2 | 0.9964 (3) | 0.2764 (3) | 0.3627 (2) | 0.0395 (8) | |
| C3 | 0.9287 (3) | 0.3122 (3) | 0.27838 (19) | 0.0325 (7) | |
| C4 | 0.9752 (3) | 0.2621 (3) | 0.20979 (19) | 0.0310 (7) | |
| H4A | 1.0391 | 0.2015 | 0.2174 | 0.037* | |
| C5 | 0.9293 (3) | 0.2995 (3) | 0.13026 (19) | 0.0303 (7) | |
| C6 | 0.8349 (3) | 0.3941 (3) | 0.1185 (2) | 0.0328 (7) | |
| C7 | 0.7857 (3) | 0.4424 (3) | 0.18563 (19) | 0.0316 (7) | |
| H7A | 0.7229 | 0.5039 | 0.1782 | 0.038* | |
| C8 | 0.8291 (3) | 0.4000 (3) | 0.26530 (19) | 0.0323 (7) | |
| C9 | 1.0556 (4) | 0.1520 (3) | 0.0662 (2) | 0.0520 (10) | |
| H9A | 1.0762 | 0.1303 | 0.0118 | 0.078* | |
| H9B | 1.0112 | 0.0863 | 0.0896 | 0.078* | |
| H9C | 1.1368 | 0.1706 | 0.1016 | 0.078* | |
| C10 | 0.7202 (3) | 0.5334 (3) | 0.0212 (2) | 0.0368 (8) | |
| H10A | 0.7556 | 0.5999 | 0.0560 | 0.044* | |
| H10B | 0.6301 | 0.5165 | 0.0332 | 0.044* | |
| C11 | 0.7190 (3) | 0.5643 (3) | −0.0687 (2) | 0.0380 (8) | |
| H11A | 0.6879 | 0.4957 | −0.1027 | 0.046* | |
| H11B | 0.8094 | 0.5827 | −0.0796 | 0.046* | |
| C12 | 0.6288 (3) | 0.6713 (3) | −0.0931 (2) | 0.0404 (8) | |
| H12A | 0.5364 | 0.6474 | −0.0922 | 0.048* | |
| H12B | 0.6488 | 0.7343 | −0.0519 | 0.048* | |
| C13 | 0.5908 (4) | 0.6370 (3) | −0.2416 (2) | 0.0462 (9) | |
| H13A | 0.4957 | 0.6258 | −0.2401 | 0.055* | |
| H13B | 0.6340 | 0.5595 | −0.2326 | 0.055* | |
| C14 | 0.6130 (5) | 0.6835 (4) | −0.3253 (2) | 0.0601 (11) | |
| H14A | 0.5713 | 0.6294 | −0.3679 | 0.072* | |
| H14B | 0.7083 | 0.6848 | −0.3293 | 0.072* | |
| C15 | 0.5571 (4) | 0.8070 (4) | −0.3413 (2) | 0.0618 (11) | |
| H15A | 0.4602 | 0.8042 | −0.3471 | 0.074* | |
| H15B | 0.5837 | 0.8382 | −0.3928 | 0.074* | |
| C16 | 0.6085 (4) | 0.8881 (3) | −0.2698 (2) | 0.0509 (10) | |
| H16A | 0.5661 | 0.9661 | −0.2779 | 0.061* | |
| H16B | 0.7041 | 0.8991 | −0.2691 | 0.061* | |
| C17 | 0.5809 (4) | 0.8370 (3) | −0.1868 (2) | 0.0431 (9) | |
| H17A | 0.6163 | 0.8905 | −0.1421 | 0.052* | |
| H17B | 0.4851 | 0.8299 | −0.1860 | 0.052* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0500 (15) | 0.0488 (15) | 0.0426 (14) | −0.0022 (12) | −0.0119 (11) | 0.0005 (12) |
| O2 | 0.0646 (18) | 0.0432 (16) | 0.0596 (17) | 0.0030 (13) | 0.0019 (13) | 0.0194 (13) |
| O3 | 0.077 (2) | 0.079 (2) | 0.068 (2) | 0.0443 (18) | 0.0102 (16) | −0.0039 (17) |
| O4 | 0.0541 (17) | 0.083 (2) | 0.0536 (17) | 0.0055 (15) | 0.0154 (13) | 0.0086 (16) |
| O5 | 0.0454 (14) | 0.0389 (13) | 0.0358 (13) | 0.0092 (11) | 0.0006 (10) | 0.0073 (11) |
| O6 | 0.0398 (13) | 0.0429 (14) | 0.0400 (13) | 0.0103 (11) | 0.0065 (10) | −0.0039 (11) |
| N1 | 0.0279 (15) | 0.064 (2) | 0.0408 (17) | 0.0085 (15) | 0.0003 (12) | −0.0051 (16) |
| N2 | 0.0313 (14) | 0.0257 (14) | 0.0365 (14) | 0.0058 (11) | 0.0010 (11) | 0.0049 (12) |
| C1 | 0.054 (3) | 0.085 (3) | 0.046 (2) | −0.005 (2) | −0.0129 (18) | 0.001 (2) |
| C2 | 0.0359 (19) | 0.042 (2) | 0.0406 (19) | 0.0052 (16) | 0.0040 (15) | 0.0079 (17) |
| C3 | 0.0281 (17) | 0.0323 (18) | 0.0358 (18) | −0.0028 (14) | −0.0015 (13) | 0.0014 (14) |
| C4 | 0.0257 (16) | 0.0305 (17) | 0.0369 (18) | 0.0034 (13) | 0.0052 (13) | −0.0002 (14) |
| C5 | 0.0249 (16) | 0.0276 (17) | 0.0385 (18) | −0.0009 (13) | 0.0038 (13) | −0.0059 (14) |
| C6 | 0.0273 (17) | 0.0325 (18) | 0.0369 (18) | −0.0028 (13) | −0.0024 (13) | 0.0020 (14) |
| C7 | 0.0249 (16) | 0.0341 (18) | 0.0356 (17) | 0.0060 (14) | 0.0025 (13) | 0.0005 (14) |
| C8 | 0.0280 (17) | 0.0339 (18) | 0.0348 (17) | 0.0045 (14) | 0.0039 (13) | −0.0040 (14) |
| C9 | 0.051 (2) | 0.045 (2) | 0.060 (2) | 0.0147 (18) | 0.0097 (18) | −0.0103 (19) |
| C10 | 0.0323 (18) | 0.0338 (18) | 0.044 (2) | 0.0052 (14) | 0.0025 (14) | 0.0066 (15) |
| C11 | 0.0389 (19) | 0.0320 (18) | 0.0419 (19) | 0.0012 (15) | 0.0009 (15) | 0.0072 (15) |
| C12 | 0.040 (2) | 0.041 (2) | 0.0394 (19) | 0.0064 (16) | 0.0013 (15) | 0.0054 (16) |
| C13 | 0.051 (2) | 0.041 (2) | 0.043 (2) | 0.0069 (17) | −0.0037 (16) | −0.0023 (17) |
| C14 | 0.077 (3) | 0.058 (3) | 0.043 (2) | 0.007 (2) | −0.0016 (19) | −0.004 (2) |
| C15 | 0.070 (3) | 0.071 (3) | 0.043 (2) | 0.011 (2) | −0.0005 (19) | 0.013 (2) |
| C16 | 0.055 (2) | 0.045 (2) | 0.054 (2) | 0.0093 (18) | 0.0088 (18) | 0.0187 (19) |
| C17 | 0.045 (2) | 0.0331 (19) | 0.051 (2) | 0.0104 (16) | 0.0081 (16) | 0.0028 (17) |
| O1—C2 | 1.332 (4) | C9—H9A | 0.9600 |
| O1—C1 | 1.442 (4) | C9—H9B | 0.9600 |
| O2—C2 | 1.187 (4) | C9—H9C | 0.9600 |
| O3—N1 | 1.235 (4) | C10—C11 | 1.492 (4) |
| O4—N1 | 1.240 (4) | C10—H10A | 0.9700 |
| O5—C6 | 1.362 (4) | C10—H10B | 0.9700 |
| O5—C10 | 1.439 (4) | C11—C12 | 1.521 (4) |
| O6—C5 | 1.352 (4) | C11—H11A | 0.9700 |
| O6—C9 | 1.432 (4) | C11—H11B | 0.9700 |
| N1—C8 | 1.422 (4) | C12—H12A | 0.9700 |
| N2—C12 | 1.439 (4) | C12—H12B | 0.9700 |
| N2—C17 | 1.464 (4) | C13—C14 | 1.492 (5) |
| N2—C13 | 1.466 (4) | C13—H13A | 0.9700 |
| C1—H1A | 0.9600 | C13—H13B | 0.9700 |
| C1—H1B | 0.9600 | C14—C15 | 1.498 (6) |
| C1—H1C | 0.9600 | C14—H14A | 0.9700 |
| C2—C3 | 1.499 (4) | C14—H14B | 0.9700 |
| C3—C4 | 1.375 (4) | C15—C16 | 1.506 (6) |
| C3—C8 | 1.398 (4) | C15—H15A | 0.9700 |
| C4—C5 | 1.375 (4) | C15—H15B | 0.9700 |
| C4—H4A | 0.9300 | C16—C17 | 1.514 (5) |
| C5—C6 | 1.416 (4) | C16—H16A | 0.9700 |
| C6—C7 | 1.360 (4) | C16—H16B | 0.9700 |
| C7—C8 | 1.389 (4) | C17—H17A | 0.9700 |
| C7—H7A | 0.9300 | C17—H17B | 0.9700 |
| C2—O1—C1 | 117.1 (3) | O5—C10—H10B | 110.2 |
| C6—O5—C10 | 117.9 (2) | C11—C10—H10B | 110.2 |
| C5—O6—C9 | 118.3 (3) | H10A—C10—H10B | 108.5 |
| O3—N1—O4 | 120.9 (3) | C10—C11—C12 | 111.3 (3) |
| O3—N1—C8 | 119.1 (3) | C10—C11—H11A | 109.4 |
| O4—N1—C8 | 119.9 (3) | C12—C11—H11A | 109.4 |
| C12—N2—C17 | 111.4 (3) | C10—C11—H11B | 109.4 |
| C12—N2—C13 | 112.3 (3) | C12—C11—H11B | 109.4 |
| C17—N2—C13 | 110.2 (3) | H11A—C11—H11B | 108.0 |
| O1—C1—H1A | 109.5 | N2—C12—C11 | 113.3 (3) |
| O1—C1—H1B | 109.5 | N2—C12—H12A | 108.9 |
| H1A—C1—H1B | 109.5 | C11—C12—H12A | 108.9 |
| O1—C1—H1C | 109.5 | N2—C12—H12B | 108.9 |
| H1A—C1—H1C | 109.5 | C11—C12—H12B | 108.9 |
| H1B—C1—H1C | 109.5 | H12A—C12—H12B | 107.7 |
| O2—C2—O1 | 125.0 (3) | N2—C13—C14 | 112.1 (3) |
| O2—C2—C3 | 124.1 (3) | N2—C13—H13A | 109.2 |
| O1—C2—C3 | 110.5 (3) | C14—C13—H13A | 109.2 |
| C4—C3—C8 | 118.2 (3) | N2—C13—H13B | 109.2 |
| C4—C3—C2 | 117.5 (3) | C14—C13—H13B | 109.2 |
| C8—C3—C2 | 124.0 (3) | H13A—C13—H13B | 107.9 |
| C5—C4—C3 | 121.5 (3) | C13—C14—C15 | 112.3 (3) |
| C5—C4—H4A | 119.3 | C13—C14—H14A | 109.1 |
| C3—C4—H4A | 119.3 | C15—C14—H14A | 109.1 |
| O6—C5—C4 | 125.2 (3) | C13—C14—H14B | 109.1 |
| O6—C5—C6 | 115.3 (3) | C15—C14—H14B | 109.1 |
| C4—C5—C6 | 119.5 (3) | H14A—C14—H14B | 107.9 |
| C7—C6—O5 | 126.1 (3) | C14—C15—C16 | 109.5 (3) |
| C7—C6—C5 | 119.6 (3) | C14—C15—H15A | 109.8 |
| O5—C6—C5 | 114.4 (3) | C16—C15—H15A | 109.8 |
| C6—C7—C8 | 120.1 (3) | C14—C15—H15B | 109.8 |
| C6—C7—H7A | 120.0 | C16—C15—H15B | 109.8 |
| C8—C7—H7A | 120.0 | H15A—C15—H15B | 108.2 |
| C7—C8—C3 | 120.9 (3) | C15—C16—C17 | 111.7 (3) |
| C7—C8—N1 | 119.2 (3) | C15—C16—H16A | 109.3 |
| C3—C8—N1 | 119.8 (3) | C17—C16—H16A | 109.3 |
| O6—C9—H9A | 109.5 | C15—C16—H16B | 109.3 |
| O6—C9—H9B | 109.5 | C17—C16—H16B | 109.3 |
| H9A—C9—H9B | 109.5 | H16A—C16—H16B | 107.9 |
| O6—C9—H9C | 109.5 | N2—C17—C16 | 109.7 (3) |
| H9A—C9—H9C | 109.5 | N2—C17—H17A | 109.7 |
| H9B—C9—H9C | 109.5 | C16—C17—H17A | 109.7 |
| O5—C10—C11 | 107.4 (3) | N2—C17—H17B | 109.7 |
| O5—C10—H10A | 110.2 | C16—C17—H17B | 109.7 |
| C11—C10—H10A | 110.2 | H17A—C17—H17B | 108.2 |
| C1—O1—C2—O2 | −1.6 (5) | C4—C3—C8—C7 | −5.0 (5) |
| C1—O1—C2—C3 | −175.4 (3) | C2—C3—C8—C7 | 169.6 (3) |
| O2—C2—C3—C4 | −55.8 (5) | C4—C3—C8—N1 | 173.9 (3) |
| O1—C2—C3—C4 | 118.1 (3) | C2—C3—C8—N1 | −11.5 (5) |
| O2—C2—C3—C8 | 129.6 (4) | O3—N1—C8—C7 | −25.2 (5) |
| O1—C2—C3—C8 | −56.6 (4) | O4—N1—C8—C7 | 153.9 (3) |
| C8—C3—C4—C5 | 2.3 (5) | O3—N1—C8—C3 | 155.8 (3) |
| C2—C3—C4—C5 | −172.7 (3) | O4—N1—C8—C3 | −25.0 (5) |
| C9—O6—C5—C4 | 7.4 (4) | C6—O5—C10—C11 | 171.1 (3) |
| C9—O6—C5—C6 | −174.4 (3) | O5—C10—C11—C12 | 177.9 (3) |
| C3—C4—C5—O6 | −180.0 (3) | C17—N2—C12—C11 | −166.2 (3) |
| C3—C4—C5—C6 | 1.8 (5) | C13—N2—C12—C11 | 69.6 (4) |
| C10—O5—C6—C7 | 5.7 (4) | C10—C11—C12—N2 | 168.9 (3) |
| C10—O5—C6—C5 | −173.2 (3) | C12—N2—C13—C14 | −176.9 (3) |
| O6—C5—C6—C7 | 178.3 (3) | C17—N2—C13—C14 | 58.3 (4) |
| C4—C5—C6—C7 | −3.4 (4) | N2—C13—C14—C15 | −55.0 (4) |
| O6—C5—C6—O5 | −2.8 (4) | C13—C14—C15—C16 | 51.9 (5) |
| C4—C5—C6—O5 | 175.6 (3) | C14—C15—C16—C17 | −54.0 (5) |
| O5—C6—C7—C8 | −178.2 (3) | C12—N2—C17—C16 | 175.3 (3) |
| C5—C6—C7—C8 | 0.7 (5) | C13—N2—C17—C16 | −59.3 (4) |
| C6—C7—C8—C3 | 3.5 (5) | C15—C16—C17—N2 | 58.5 (4) |
| C6—C7—C8—N1 | −175.4 (3) |
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
Enraf–Nonius (1994). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Knesl, P., Roeseling, D. & Jordis, U. (2006). Molecules, 11, 286–297.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
As part of our ongoing studies on quinazoline derivatives (Knesl et al., 2006), we report herein the crystal structure of the title compound, (I).
In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Ring A (C4-C9) is, of course, planar.