organic compounds
The herbicide 3-phenyl-1-(2-hydroxy-3-iodo-4,6-dimethoxyphenyl)propen-1-one, C17H15IO4, exists as a nearly planar molecule; the hydroxy group forms an intramolecular hydrogen bond with the carbonyl O atom.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028984/wk2020sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028984/wk2020Isup2.hkl |
CCDC reference: 621515
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.
Styryl(2-hydroxy-3-iodo-4,6-dimethoxyphenyl)ketone top
Crystal data top
C17H15IO4 | F(000) = 808 |
Mr = 410.19 | Dx = 1.734 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 15509 reflections |
a = 8.199 (2) Å | θ = 3.1–27.4° |
b = 14.468 (3) Å | µ = 2.05 mm−1 |
c = 13.245 (3) Å | T = 295 K |
V = 1571.2 (5) Å3 | Block, colorless |
Z = 4 | 0.40 × 0.30 × 0.20 mm |
Data collection top
Rigaku R-AXIS RAPID IP diffractometer | 3522 independent reflections |
Radiation source: fine-focus sealed tube | 3316 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ω scans | θmax = 27.4°, θmin = 3.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −10→10 |
Tmin = 0.406, Tmax = 0.684 | k = −17→18 |
13818 measured reflections | l = −17→17 |
Refinement top
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)] = 0.027 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.067 | w = 1/[σ2(Fo2) + (0.0376P)2 + 0.5885P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.001 |
3522 reflections | Δρmax = 0.26 e Å−3 |
205 parameters | Δρmin = −0.56 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 1656 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.03 (2) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
I1 | 0.41910 (2) | 0.071494 (13) | 0.50000 (2) | 0.04715 (8) | |
O1 | 0.7799 (4) | 0.05639 (17) | 0.1532 (2) | 0.0588 (7) | |
O2 | 0.6193 (4) | 0.03526 (17) | 0.3060 (2) | 0.0518 (6) | |
H2o | 0.685 (5) | 0.033 (4) | 0.256 (3) | 0.071 (15)* | |
O3 | 0.4224 (3) | 0.28669 (17) | 0.4880 (3) | 0.0501 (7) | |
O4 | 0.7313 (3) | 0.33960 (15) | 0.18645 (19) | 0.0489 (6) | |
C1 | 1.0519 (6) | 0.1321 (3) | −0.1652 (3) | 0.0577 (10) | |
H1 | 1.0488 | 0.0687 | −0.1536 | 0.069* | |
C2 | 1.1220 (6) | 0.1653 (3) | −0.2535 (3) | 0.0636 (11) | |
H2 | 1.1674 | 0.1247 | −0.3001 | 0.076* | |
C3 | 1.1232 (6) | 0.2581 (4) | −0.2710 (4) | 0.0632 (11) | |
H3 | 1.1688 | 0.2809 | −0.3303 | 0.076* | |
C4 | 1.0575 (6) | 0.3185 (3) | −0.2016 (4) | 0.0666 (12) | |
H4 | 1.0589 | 0.3817 | −0.2144 | 0.080* | |
C5 | 0.9899 (6) | 0.2860 (3) | −0.1137 (3) | 0.0551 (9) | |
H5 | 0.9464 | 0.3273 | −0.0671 | 0.066* | |
C6 | 0.9864 (5) | 0.1918 (2) | −0.0940 (3) | 0.0436 (7) | |
C7 | 0.9132 (4) | 0.1520 (2) | −0.0032 (5) | 0.0490 (7) | |
H7 | 0.9259 | 0.0886 | 0.0048 | 0.059* | |
C8 | 0.8316 (5) | 0.1946 (2) | 0.0686 (3) | 0.0459 (7) | |
H8 | 0.8169 | 0.2582 | 0.0651 | 0.055* | |
C9 | 0.7639 (4) | 0.1432 (2) | 0.1539 (2) | 0.0416 (7) | |
C10 | 0.6747 (4) | 0.1860 (2) | 0.2380 (2) | 0.0358 (6) | |
C11 | 0.6052 (4) | 0.1276 (2) | 0.3122 (3) | 0.0390 (7) | |
C12 | 0.5199 (4) | 0.1627 (2) | 0.3946 (2) | 0.0386 (6) | |
C13 | 0.5043 (4) | 0.2572 (2) | 0.4069 (2) | 0.0382 (6) | |
C14 | 0.5747 (4) | 0.3175 (2) | 0.3365 (3) | 0.0395 (7) | |
H14 | 0.5649 | 0.3810 | 0.3454 | 0.047* | |
C15 | 0.6582 (4) | 0.2834 (2) | 0.2544 (3) | 0.0361 (6) | |
C16 | 0.4115 (4) | 0.3824 (2) | 0.5091 (5) | 0.0528 (9) | |
H16a | 0.3549 | 0.3914 | 0.5718 | 0.079* | |
H16b | 0.3531 | 0.4128 | 0.4557 | 0.079* | |
H16c | 0.5193 | 0.4080 | 0.5141 | 0.079* | |
C17 | 0.7178 (6) | 0.4378 (2) | 0.1995 (4) | 0.0562 (10) | |
H17a | 0.7796 | 0.4686 | 0.1479 | 0.084* | |
H17b | 0.7595 | 0.4548 | 0.2646 | 0.084* | |
H17c | 0.6054 | 0.4558 | 0.1945 | 0.084* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.05262 (12) | 0.04387 (11) | 0.04494 (11) | −0.00181 (8) | 0.00436 (14) | 0.01005 (12) |
O1 | 0.084 (2) | 0.0375 (13) | 0.0549 (16) | 0.0029 (12) | 0.0141 (15) | −0.0055 (10) |
O2 | 0.0690 (17) | 0.0301 (11) | 0.0563 (15) | 0.0003 (11) | 0.0113 (13) | 0.0013 (11) |
O3 | 0.0588 (12) | 0.0457 (11) | 0.046 (2) | 0.0021 (10) | 0.0113 (13) | −0.0030 (11) |
O4 | 0.0631 (16) | 0.0341 (11) | 0.0496 (13) | −0.0033 (11) | 0.0117 (12) | 0.0045 (9) |
C1 | 0.076 (3) | 0.047 (2) | 0.051 (2) | 0.0085 (18) | 0.0085 (19) | 0.0002 (16) |
C2 | 0.071 (3) | 0.068 (3) | 0.051 (2) | 0.012 (2) | 0.017 (2) | 0.001 (2) |
C3 | 0.062 (3) | 0.072 (3) | 0.056 (2) | 0.004 (2) | 0.012 (2) | 0.016 (2) |
C4 | 0.077 (3) | 0.047 (2) | 0.076 (3) | 0.0018 (19) | 0.009 (2) | 0.015 (2) |
C5 | 0.061 (2) | 0.0465 (19) | 0.058 (2) | 0.0035 (18) | 0.006 (2) | −0.0020 (16) |
C6 | 0.0494 (19) | 0.0425 (17) | 0.0389 (16) | 0.0021 (14) | −0.0045 (15) | −0.0019 (13) |
C7 | 0.0621 (17) | 0.0414 (14) | 0.0435 (15) | 0.0017 (13) | 0.003 (2) | 0.001 (2) |
C8 | 0.052 (2) | 0.0436 (17) | 0.0422 (16) | 0.0031 (15) | 0.0035 (15) | 0.0002 (13) |
C9 | 0.0441 (17) | 0.0423 (17) | 0.0382 (15) | −0.0027 (14) | −0.0039 (15) | −0.0039 (12) |
C10 | 0.0386 (16) | 0.0347 (14) | 0.0341 (14) | −0.0018 (12) | −0.0041 (13) | −0.0011 (11) |
C11 | 0.0408 (17) | 0.0349 (15) | 0.0413 (15) | −0.0011 (12) | −0.0073 (13) | −0.0006 (12) |
C12 | 0.0392 (16) | 0.0365 (15) | 0.0402 (16) | −0.0010 (12) | −0.0026 (13) | 0.0054 (12) |
C13 | 0.0333 (14) | 0.0413 (16) | 0.0400 (14) | 0.0018 (12) | −0.0035 (14) | −0.0014 (12) |
C14 | 0.0432 (17) | 0.0286 (14) | 0.0465 (17) | 0.0015 (12) | −0.0057 (14) | −0.0002 (12) |
C15 | 0.0366 (17) | 0.0337 (15) | 0.0381 (16) | 0.0000 (13) | −0.0048 (13) | 0.0041 (12) |
C16 | 0.0546 (17) | 0.0449 (16) | 0.059 (2) | 0.0013 (13) | 0.016 (2) | −0.009 (2) |
C17 | 0.068 (3) | 0.0340 (17) | 0.066 (2) | −0.0039 (16) | 0.011 (2) | 0.0100 (15) |
Geometric parameters (Å, º) top
I1—C12 | 2.091 (3) | C6—C7 | 1.462 (7) |
O1—C9 | 1.262 (4) | C7—C8 | 1.316 (6) |
O2—C11 | 1.344 (4) | C7—H7 | 0.9300 |
O2—H2o | 0.85 (1) | C8—C9 | 1.462 (5) |
O3—C13 | 1.336 (5) | C8—H8 | 0.9300 |
O3—C16 | 1.416 (4) | C9—C10 | 1.469 (5) |
O4—C15 | 1.352 (4) | C10—C11 | 1.416 (4) |
O4—C17 | 1.436 (4) | C10—C15 | 1.432 (5) |
C1—C6 | 1.387 (5) | C11—C12 | 1.392 (5) |
C1—C2 | 1.390 (6) | C12—C13 | 1.383 (5) |
C1—H1 | 0.9300 | C13—C14 | 1.401 (5) |
C2—C3 | 1.363 (7) | C14—C15 | 1.377 (5) |
C2—H2 | 0.9300 | C14—H14 | 0.9300 |
C3—C4 | 1.378 (7) | C16—H16a | 0.9600 |
C3—H3 | 0.9300 | C16—H16b | 0.9600 |
C4—C5 | 1.372 (6) | C16—H16c | 0.9600 |
C4—H4 | 0.9300 | C17—H17a | 0.9600 |
C5—C6 | 1.388 (5) | C17—H17b | 0.9600 |
C5—H5 | 0.9300 | C17—H17c | 0.9600 |
C11—O2—H2o | 98 (4) | C11—C10—C15 | 116.4 (3) |
C13—O3—C16 | 120.2 (4) | C11—C10—C9 | 118.3 (3) |
C15—O4—C17 | 118.8 (3) | C15—C10—C9 | 125.2 (3) |
C6—C1—C2 | 121.1 (4) | O2—C11—C12 | 117.0 (3) |
C6—C1—H1 | 119.4 | O2—C11—C10 | 121.1 (3) |
C2—C1—H1 | 119.4 | C12—C11—C10 | 122.0 (3) |
C3—C2—C1 | 119.2 (4) | C13—C12—C11 | 119.9 (3) |
C3—C2—H2 | 120.4 | C13—C12—I1 | 120.6 (2) |
C1—C2—H2 | 120.4 | C11—C12—I1 | 119.5 (2) |
C2—C3—C4 | 120.5 (4) | O3—C13—C12 | 117.2 (3) |
C2—C3—H3 | 119.7 | O3—C13—C14 | 122.9 (3) |
C4—C3—H3 | 119.7 | C12—C13—C14 | 119.9 (3) |
C5—C4—C3 | 120.5 (4) | C15—C14—C13 | 120.5 (3) |
C5—C4—H4 | 119.7 | C15—C14—H14 | 119.7 |
C3—C4—H4 | 119.7 | C13—C14—H14 | 119.7 |
C4—C5—C6 | 120.2 (4) | O4—C15—C14 | 122.1 (3) |
C4—C5—H5 | 119.9 | O4—C15—C10 | 116.7 (3) |
C6—C5—H5 | 119.9 | C14—C15—C10 | 121.2 (3) |
C1—C6—C5 | 118.4 (4) | O3—C16—H16a | 109.5 |
C1—C6—C7 | 118.2 (3) | O3—C16—H16b | 109.5 |
C5—C6—C7 | 123.3 (3) | H16a—C16—H16b | 109.5 |
C8—C7—C6 | 128.3 (3) | O3—C16—H16c | 109.5 |
C8—C7—H7 | 115.9 | H16a—C16—H16c | 109.5 |
C6—C7—H7 | 115.9 | H16b—C16—H16c | 109.5 |
C7—C8—C9 | 120.9 (3) | O4—C17—H17a | 109.5 |
C7—C8—H8 | 119.5 | O4—C17—H17b | 109.5 |
C9—C8—H8 | 119.5 | H17a—C17—H17b | 109.5 |
O1—C9—C8 | 117.4 (3) | O4—C17—H17c | 109.5 |
O1—C9—C10 | 118.5 (3) | H17a—C17—H17c | 109.5 |
C8—C9—C10 | 124.1 (3) | H17b—C17—H17c | 109.5 |
C6—C1—C2—C3 | −1.3 (8) | O2—C11—C12—C13 | 178.5 (3) |
C1—C2—C3—C4 | 0.7 (8) | C10—C11—C12—C13 | −1.5 (5) |
C2—C3—C4—C5 | 0.1 (8) | O2—C11—C12—I1 | −0.7 (4) |
C3—C4—C5—C6 | −0.4 (8) | C10—C11—C12—I1 | 179.4 (2) |
C2—C1—C6—C5 | 1.0 (7) | C16—O3—C13—C12 | 175.6 (4) |
C2—C1—C6—C7 | 179.4 (4) | C16—O3—C13—C14 | −3.6 (6) |
C4—C5—C6—C1 | −0.2 (6) | C11—C12—C13—O3 | −179.3 (3) |
C4—C5—C6—C7 | −178.5 (4) | I1—C12—C13—O3 | −0.2 (4) |
C1—C6—C7—C8 | −173.1 (4) | C11—C12—C13—C14 | −0.2 (5) |
C5—C6—C7—C8 | 5.2 (7) | I1—C12—C13—C14 | 179.0 (2) |
C6—C7—C8—C9 | 178.9 (4) | O3—C13—C14—C15 | 179.8 (3) |
C7—C8—C9—O1 | −3.3 (6) | C12—C13—C14—C15 | 0.7 (5) |
C7—C8—C9—C10 | 178.6 (4) | C17—O4—C15—C14 | −1.4 (5) |
O1—C9—C10—C11 | −2.5 (5) | C17—O4—C15—C10 | 179.8 (3) |
C8—C9—C10—C11 | 175.5 (3) | C13—C14—C15—O4 | −178.3 (3) |
O1—C9—C10—C15 | 174.3 (3) | C13—C14—C15—C10 | 0.4 (5) |
C8—C9—C10—C15 | −7.7 (5) | C11—C10—C15—O4 | 176.8 (3) |
C15—C10—C11—O2 | −177.5 (3) | C9—C10—C15—O4 | 0.0 (5) |
C9—C10—C11—O2 | −0.4 (5) | C11—C10—C15—C14 | −1.9 (5) |
C15—C10—C11—C12 | 2.4 (5) | C9—C10—C15—C14 | −178.8 (3) |
C9—C10—C11—C12 | 179.5 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2o···O1 | 0.85 (1) | 1.61 (2) | 2.434 (4) | 163 (5) |