organic compounds
In the title compound, C18H16O6, a herbicide, the dioxole ring adopts a flattened envelope conformation. The two aromatic rings at either end of the propenone linkage are almost coplanar with it. The hydroxy group is involved in an intramolecular O—HO hydrogen bond.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028017/ci2112sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028017/ci2112Isup2.hkl |
CCDC reference: 618171
Computing details top
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
(E)-3-(1,3-Benzodioxol-5-yl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one top
Crystal data top
C18H16O6 | F(000) = 688 |
Mr = 328.31 | Dx = 1.444 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 13707 reflections |
a = 4.0062 (2) Å | θ = 3.3–27.3° |
b = 13.6947 (9) Å | µ = 0.11 mm−1 |
c = 27.530 (2) Å | T = 295 K |
V = 1510.4 (2) Å3 | Block, colourless |
Z = 4 | 0.4 × 0.3 × 0.2 mm |
Data collection top
Rigaku R-AXIS RAPID IP diffractometer | 2031 independent reflections |
Radiation source: fine-focus sealed tube | 1877 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ω scans | θmax = 27.3°, θmin = 3.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −5→4 |
Tmin = 0.724, Tmax = 1.00 | k = −17→17 |
13868 measured reflections | l = −35→35 |
Refinement top
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0667P)2 + 0.1168P] where P = (Fo2 + 2Fc2)/3 |
2031 reflections | (Δ/σ)max = 0.001 |
223 parameters | Δρmax = 0.17 e Å−3 |
1 restraint | Δρmin = −0.13 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.7456 (6) | 0.97036 (11) | −0.13313 (5) | 0.0750 (5) | |
O2 | 0.5771 (5) | 1.11196 (11) | −0.17122 (5) | 0.0707 (5) | |
O3 | 0.0901 (5) | 1.06246 (10) | 0.12149 (5) | 0.0676 (4) | |
O4 | 0.0485 (5) | 0.98856 (9) | 0.20236 (5) | 0.0590 (4) | |
H4o | 0.029 (9) | 1.0231 (15) | 0.1761 (6) | 0.078 (8)* | |
O5 | 0.5359 (4) | 0.67967 (10) | 0.23192 (5) | 0.0593 (4) | |
O6 | 0.6102 (4) | 0.81448 (10) | 0.07501 (4) | 0.0586 (4) | |
C1 | 0.7091 (7) | 1.01586 (16) | −0.17909 (7) | 0.0665 (6) | |
H1a | 0.5584 | 0.9783 | −0.1994 | 0.080* | |
H1b | 0.9237 | 1.0199 | −0.1953 | 0.080* | |
C2 | 0.5919 (6) | 1.03098 (13) | −0.10013 (7) | 0.0516 (4) | |
C3 | 0.4933 (6) | 1.11585 (13) | −0.12281 (6) | 0.0518 (4) | |
C4 | 0.3389 (6) | 1.18975 (14) | −0.09809 (7) | 0.0581 (5) | |
H4 | 0.2774 | 1.2476 | −0.1133 | 0.070* | |
C5 | 0.2782 (6) | 1.17380 (13) | −0.04876 (7) | 0.0530 (4) | |
H5 | 0.1696 | 1.2220 | −0.0310 | 0.064* | |
C6 | 0.3747 (5) | 1.08797 (11) | −0.02515 (6) | 0.0462 (4) | |
C7 | 0.5414 (6) | 1.01510 (12) | −0.05175 (6) | 0.0505 (4) | |
H7 | 0.6148 | 0.9580 | −0.0369 | 0.061* | |
C8 | 0.2893 (5) | 1.07503 (13) | 0.02614 (6) | 0.0502 (4) | |
H8 | 0.1691 | 1.1251 | 0.0408 | 0.060* | |
C9 | 0.3663 (6) | 0.99894 (14) | 0.05380 (6) | 0.0552 (5) | |
H9 | 0.4928 | 0.9484 | 0.0407 | 0.066* | |
C10 | 0.2558 (5) | 0.99271 (13) | 0.10480 (6) | 0.0494 (4) | |
C11 | 0.3330 (5) | 0.90890 (12) | 0.13592 (6) | 0.0437 (4) | |
C12 | 0.2224 (5) | 0.91222 (12) | 0.18516 (6) | 0.0454 (4) | |
C13 | 0.2864 (5) | 0.83802 (13) | 0.21822 (6) | 0.0473 (4) | |
H13 | 0.2123 | 0.8429 | 0.2501 | 0.057* | |
C14 | 0.4604 (5) | 0.75738 (13) | 0.20310 (6) | 0.0464 (4) | |
C15 | 0.5723 (5) | 0.74879 (13) | 0.15511 (6) | 0.0489 (4) | |
H15 | 0.6886 | 0.6934 | 0.1454 | 0.059* | |
C16 | 0.5098 (5) | 0.82231 (12) | 0.12254 (6) | 0.0450 (4) | |
C17 | 0.4189 (7) | 0.68321 (16) | 0.28098 (7) | 0.0628 (5) | |
H17a | 0.4730 | 0.6231 | 0.2971 | 0.094* | |
H17b | 0.1814 | 0.6924 | 0.2811 | 0.094* | |
H17c | 0.5240 | 0.7366 | 0.2976 | 0.094* | |
C18 | 0.7754 (6) | 0.72696 (15) | 0.06089 (7) | 0.0623 (5) | |
H18a | 0.8369 | 0.7311 | 0.0273 | 0.093* | |
H18b | 0.6284 | 0.6724 | 0.0656 | 0.093* | |
H18c | 0.9722 | 0.7184 | 0.0803 | 0.093* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1078 (14) | 0.0646 (8) | 0.0528 (7) | 0.0252 (10) | 0.0005 (9) | −0.0062 (6) |
O2 | 0.0986 (13) | 0.0671 (8) | 0.0463 (7) | 0.0090 (10) | −0.0010 (8) | 0.0030 (6) |
O3 | 0.0910 (12) | 0.0523 (7) | 0.0596 (7) | 0.0182 (9) | 0.0087 (9) | 0.0054 (6) |
O4 | 0.0749 (9) | 0.0490 (7) | 0.0532 (7) | 0.0087 (8) | 0.0112 (8) | −0.0024 (5) |
O5 | 0.0688 (9) | 0.0533 (7) | 0.0557 (7) | 0.0048 (8) | 0.0013 (7) | 0.0109 (6) |
O6 | 0.0712 (9) | 0.0577 (7) | 0.0469 (6) | 0.0146 (8) | 0.0089 (7) | 0.0002 (5) |
C1 | 0.0741 (15) | 0.0729 (13) | 0.0526 (10) | 0.0095 (13) | 0.0013 (11) | −0.0033 (9) |
C2 | 0.0579 (11) | 0.0464 (8) | 0.0504 (9) | 0.0002 (9) | −0.0070 (9) | −0.0057 (7) |
C3 | 0.0593 (11) | 0.0500 (9) | 0.0460 (8) | −0.0052 (9) | −0.0078 (9) | 0.0025 (7) |
C4 | 0.0738 (13) | 0.0448 (9) | 0.0556 (9) | 0.0037 (10) | −0.0067 (10) | 0.0060 (7) |
C5 | 0.0612 (11) | 0.0437 (8) | 0.0541 (9) | 0.0033 (9) | −0.0019 (9) | 0.0018 (7) |
C6 | 0.0481 (9) | 0.0426 (8) | 0.0478 (8) | −0.0070 (8) | −0.0052 (7) | 0.0013 (7) |
C7 | 0.0581 (11) | 0.0412 (8) | 0.0521 (9) | 0.0000 (8) | −0.0081 (9) | 0.0024 (7) |
C8 | 0.0525 (10) | 0.0465 (8) | 0.0516 (9) | −0.0021 (9) | 0.0006 (8) | 0.0020 (7) |
C9 | 0.0638 (12) | 0.0526 (9) | 0.0492 (9) | 0.0059 (10) | 0.0016 (9) | 0.0046 (7) |
C10 | 0.0521 (10) | 0.0460 (8) | 0.0500 (9) | 0.0010 (8) | −0.0015 (8) | 0.0002 (7) |
C11 | 0.0441 (8) | 0.0431 (8) | 0.0439 (8) | −0.0026 (8) | −0.0004 (7) | −0.0014 (6) |
C12 | 0.0461 (9) | 0.0410 (8) | 0.0492 (8) | −0.0043 (8) | −0.0002 (8) | −0.0048 (7) |
C13 | 0.0498 (9) | 0.0506 (8) | 0.0417 (7) | −0.0046 (8) | 0.0018 (8) | −0.0003 (7) |
C14 | 0.0462 (9) | 0.0440 (8) | 0.0489 (8) | −0.0042 (8) | −0.0054 (8) | 0.0055 (7) |
C15 | 0.0489 (9) | 0.0457 (8) | 0.0520 (9) | 0.0031 (8) | 0.0000 (8) | −0.0011 (7) |
C16 | 0.0444 (9) | 0.0466 (8) | 0.0441 (8) | −0.0029 (8) | −0.0006 (7) | −0.0006 (7) |
C17 | 0.0654 (12) | 0.0659 (11) | 0.0571 (10) | −0.0006 (11) | 0.0016 (10) | 0.0181 (9) |
C18 | 0.0625 (12) | 0.0684 (12) | 0.0559 (10) | 0.0145 (11) | 0.0052 (10) | −0.0098 (9) |
Geometric parameters (Å, º) top
O1—C2 | 1.376 (2) | C6—C8 | 1.464 (2) |
O1—C1 | 1.418 (2) | C7—H7 | 0.93 |
O2—C3 | 1.375 (2) | C8—C9 | 1.327 (2) |
O2—C1 | 1.435 (3) | C8—H8 | 0.93 |
O3—C10 | 1.251 (2) | C9—C10 | 1.474 (3) |
O4—C12 | 1.343 (2) | C9—H9 | 0.93 |
O4—H4O | 0.87 (1) | C10—C11 | 1.465 (2) |
O5—C14 | 1.362 (2) | C11—C16 | 1.430 (2) |
O5—C17 | 1.430 (2) | C11—C12 | 1.427 (2) |
O6—C16 | 1.373 (2) | C12—C13 | 1.388 (2) |
O6—C18 | 1.423 (2) | C13—C14 | 1.371 (3) |
C1—H1a | 0.97 | C13—H13 | 0.93 |
C1—H1b | 0.97 | C14—C15 | 1.400 (2) |
C2—C7 | 1.365 (3) | C15—C16 | 1.371 (2) |
C2—C3 | 1.377 (3) | C15—H15 | 0.93 |
C3—C4 | 1.368 (3) | C17—H17a | 0.96 |
C4—C5 | 1.397 (3) | C17—H17b | 0.96 |
C4—H4 | 0.93 | C17—H17c | 0.96 |
C5—C6 | 1.398 (2) | C18—H18a | 0.96 |
C5—H5 | 0.93 | C18—H18b | 0.96 |
C6—C7 | 1.407 (3) | C18—H18c | 0.96 |
C2—O1—C1 | 106.13 (16) | C10—C9—H9 | 119.3 |
C3—O2—C1 | 105.78 (15) | O3—C10—C11 | 119.69 (16) |
C12—O4—H4o | 100.2 (18) | O3—C10—C9 | 117.71 (16) |
C14—O5—C17 | 116.82 (16) | C11—C10—C9 | 122.60 (16) |
C16—O6—C18 | 117.52 (14) | C16—C11—C12 | 115.16 (15) |
O1—C1—O2 | 107.83 (15) | C16—C11—C10 | 127.13 (15) |
O1—C1—H1a | 110.1 | C12—C11—C10 | 117.72 (15) |
O2—C1—H1a | 110.1 | O4—C12—C13 | 115.76 (16) |
O1—C1—H1b | 110.1 | O4—C12—C11 | 121.40 (15) |
O2—C1—H1b | 110.1 | C13—C12—C11 | 122.84 (16) |
H1a—C1—H1b | 108.5 | C14—C13—C12 | 118.98 (16) |
C7—C2—O1 | 127.91 (17) | C14—C13—H13 | 120.5 |
C7—C2—C3 | 122.31 (18) | C12—C13—H13 | 120.5 |
O1—C2—C3 | 109.77 (16) | O5—C14—C13 | 124.45 (16) |
C4—C3—O2 | 128.42 (17) | O5—C14—C15 | 114.40 (16) |
C4—C3—C2 | 121.92 (17) | C13—C14—C15 | 121.14 (16) |
O2—C3—C2 | 109.66 (17) | C16—C15—C14 | 119.80 (16) |
C3—C4—C5 | 116.54 (17) | C16—C15—H15 | 120.1 |
C3—C4—H4 | 121.7 | C14—C15—H15 | 120.1 |
C5—C4—H4 | 121.7 | O6—C16—C15 | 120.83 (16) |
C4—C5—C6 | 122.38 (18) | O6—C16—C11 | 117.09 (15) |
C4—C5—H5 | 118.8 | C15—C16—C11 | 122.07 (16) |
C6—C5—H5 | 118.8 | O5—C17—H17a | 109.5 |
C5—C6—C7 | 119.07 (16) | O5—C17—H17b | 109.5 |
C5—C6—C8 | 119.06 (17) | H17a—C17—H17b | 109.5 |
C7—C6—C8 | 121.84 (15) | O5—C17—H17c | 109.5 |
C2—C7—C6 | 117.75 (16) | H17a—C17—H17c | 109.5 |
C2—C7—H7 | 121.1 | H17b—C17—H17c | 109.5 |
C6—C7—H7 | 121.1 | O6—C18—H18a | 109.5 |
C9—C8—C6 | 126.46 (18) | O6—C18—H18b | 109.5 |
C9—C8—H8 | 116.8 | H18a—C18—H18b | 109.5 |
C6—C8—H8 | 116.8 | O6—C18—H18c | 109.5 |
C8—C9—C10 | 121.46 (19) | H18a—C18—H18c | 109.5 |
C8—C9—H9 | 119.3 | H18b—C18—H18c | 109.5 |
C2—O1—C1—O2 | 9.0 (3) | O3—C10—C11—C16 | 178.07 (19) |
C3—O2—C1—O1 | −8.6 (3) | C9—C10—C11—C16 | −2.0 (3) |
C1—O1—C2—C7 | 175.0 (2) | O3—C10—C11—C12 | −2.0 (3) |
C1—O1—C2—C3 | −6.1 (3) | C9—C10—C11—C12 | 178.01 (18) |
C1—O2—C3—C4 | −175.6 (2) | C16—C11—C12—O4 | −178.89 (17) |
C1—O2—C3—C2 | 4.9 (2) | C10—C11—C12—O4 | 1.1 (3) |
C7—C2—C3—C4 | 0.2 (3) | C16—C11—C12—C13 | 1.2 (3) |
O1—C2—C3—C4 | −178.8 (2) | C10—C11—C12—C13 | −178.75 (17) |
C7—C2—C3—O2 | 179.7 (2) | O4—C12—C13—C14 | 179.47 (17) |
O1—C2—C3—O2 | 0.7 (3) | C11—C12—C13—C14 | −0.7 (3) |
O2—C3—C4—C5 | 179.0 (2) | C17—O5—C14—C13 | 1.0 (3) |
C2—C3—C4—C5 | −1.6 (3) | C17—O5—C14—C15 | −178.21 (17) |
C3—C4—C5—C6 | 1.2 (3) | C12—C13—C14—O5 | −179.40 (18) |
C4—C5—C6—C7 | 0.5 (3) | C12—C13—C14—C15 | −0.3 (3) |
C4—C5—C6—C8 | −177.4 (2) | O5—C14—C15—C16 | 179.71 (17) |
O1—C2—C7—C6 | −179.5 (2) | C13—C14—C15—C16 | 0.5 (3) |
C3—C2—C7—C6 | 1.7 (3) | C18—O6—C16—C15 | 1.0 (3) |
C5—C6—C7—C2 | −2.0 (3) | C18—O6—C16—C11 | −177.69 (18) |
C8—C6—C7—C2 | 175.91 (19) | C14—C15—C16—O6 | −178.44 (17) |
C5—C6—C8—C9 | −179.0 (2) | C14—C15—C16—C11 | 0.2 (3) |
C7—C6—C8—C9 | 3.2 (3) | C12—C11—C16—O6 | 177.68 (16) |
C6—C8—C9—C10 | −177.85 (18) | C10—C11—C16—O6 | −2.3 (3) |
C8—C9—C10—O3 | −1.0 (3) | C12—C11—C16—C15 | −1.0 (3) |
C8—C9—C10—C11 | 179.1 (2) | C10—C11—C16—C15 | 178.98 (18) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4o···O3 | 0.87 (1) | 1.62 (1) | 2.451 (2) | 161 (3) |
C9—H9···O6 | 0.93 | 2.12 | 2.771 (2) | 126 |
C13—H13···O2i | 0.93 | 2.53 | 3.443 (2) | 166 |
Symmetry code: (i) −x+1/2, −y+2, z+1/2. |