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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028984/wk2020sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028984/wk2020Isup2.hkl
Contains datablock I

CCDC reference: 621515

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.027
  • wR factor = 0.067
  • Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact I1 .. O1 .. 3.19 Ang.
Alert level C PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.89 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT731_ALERT_1_C Bond Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Ra O2 -H2O 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Ra O2 -H2O 1.555 1.555
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.40 From the CIF: _reflns_number_total 3522 Count of symmetry unique reflns 1869 Completeness (_total/calc) 188.44% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1653 Fraction of Friedel pairs measured 0.884 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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
C17H15IO4F(000) = 808
Mr = 410.19Dx = 1.734 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 15509 reflections
a = 8.199 (2) Åθ = 3.1–27.4°
b = 14.468 (3) ŵ = 2.05 mm1
c = 13.245 (3) ÅT = 295 K
V = 1571.2 (5) Å3Block, colorless
Z = 40.40 × 0.30 × 0.20 mm
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
3522 independent reflections
Radiation source: fine-focus sealed tube3316 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ω scansθmax = 27.4°, θmin = 3.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1010
Tmin = 0.406, Tmax = 0.684k = 1718
13818 measured reflectionsl = 1717
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027H 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 reflectionsΔρmax = 0.26 e Å3
205 parametersΔρmin = 0.56 e Å3
2 restraintsAbsolute structure: Flack (1983), 1656 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (2)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.41910 (2)0.071494 (13)0.50000 (2)0.04715 (8)
O10.7799 (4)0.05639 (17)0.1532 (2)0.0588 (7)
O20.6193 (4)0.03526 (17)0.3060 (2)0.0518 (6)
H2o0.685 (5)0.033 (4)0.256 (3)0.071 (15)*
O30.4224 (3)0.28669 (17)0.4880 (3)0.0501 (7)
O40.7313 (3)0.33960 (15)0.18645 (19)0.0489 (6)
C11.0519 (6)0.1321 (3)0.1652 (3)0.0577 (10)
H11.04880.06870.15360.069*
C21.1220 (6)0.1653 (3)0.2535 (3)0.0636 (11)
H21.16740.12470.30010.076*
C31.1232 (6)0.2581 (4)0.2710 (4)0.0632 (11)
H31.16880.28090.33030.076*
C41.0575 (6)0.3185 (3)0.2016 (4)0.0666 (12)
H41.05890.38170.21440.080*
C50.9899 (6)0.2860 (3)0.1137 (3)0.0551 (9)
H50.94640.32730.06710.066*
C60.9864 (5)0.1918 (2)0.0940 (3)0.0436 (7)
C70.9132 (4)0.1520 (2)0.0032 (5)0.0490 (7)
H70.92590.08860.00480.059*
C80.8316 (5)0.1946 (2)0.0686 (3)0.0459 (7)
H80.81690.25820.06510.055*
C90.7639 (4)0.1432 (2)0.1539 (2)0.0416 (7)
C100.6747 (4)0.1860 (2)0.2380 (2)0.0358 (6)
C110.6052 (4)0.1276 (2)0.3122 (3)0.0390 (7)
C120.5199 (4)0.1627 (2)0.3946 (2)0.0386 (6)
C130.5043 (4)0.2572 (2)0.4069 (2)0.0382 (6)
C140.5747 (4)0.3175 (2)0.3365 (3)0.0395 (7)
H140.56490.38100.34540.047*
C150.6582 (4)0.2834 (2)0.2544 (3)0.0361 (6)
C160.4115 (4)0.3824 (2)0.5091 (5)0.0528 (9)
H16a0.35490.39140.57180.079*
H16b0.35310.41280.45570.079*
H16c0.51930.40800.51410.079*
C170.7178 (6)0.4378 (2)0.1995 (4)0.0562 (10)
H17a0.77960.46860.14790.084*
H17b0.75950.45480.26460.084*
H17c0.60540.45580.19450.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.05262 (12)0.04387 (11)0.04494 (11)0.00181 (8)0.00436 (14)0.01005 (12)
O10.084 (2)0.0375 (13)0.0549 (16)0.0029 (12)0.0141 (15)0.0055 (10)
O20.0690 (17)0.0301 (11)0.0563 (15)0.0003 (11)0.0113 (13)0.0013 (11)
O30.0588 (12)0.0457 (11)0.046 (2)0.0021 (10)0.0113 (13)0.0030 (11)
O40.0631 (16)0.0341 (11)0.0496 (13)0.0033 (11)0.0117 (12)0.0045 (9)
C10.076 (3)0.047 (2)0.051 (2)0.0085 (18)0.0085 (19)0.0002 (16)
C20.071 (3)0.068 (3)0.051 (2)0.012 (2)0.017 (2)0.001 (2)
C30.062 (3)0.072 (3)0.056 (2)0.004 (2)0.012 (2)0.016 (2)
C40.077 (3)0.047 (2)0.076 (3)0.0018 (19)0.009 (2)0.015 (2)
C50.061 (2)0.0465 (19)0.058 (2)0.0035 (18)0.006 (2)0.0020 (16)
C60.0494 (19)0.0425 (17)0.0389 (16)0.0021 (14)0.0045 (15)0.0019 (13)
C70.0621 (17)0.0414 (14)0.0435 (15)0.0017 (13)0.003 (2)0.001 (2)
C80.052 (2)0.0436 (17)0.0422 (16)0.0031 (15)0.0035 (15)0.0002 (13)
C90.0441 (17)0.0423 (17)0.0382 (15)0.0027 (14)0.0039 (15)0.0039 (12)
C100.0386 (16)0.0347 (14)0.0341 (14)0.0018 (12)0.0041 (13)0.0011 (11)
C110.0408 (17)0.0349 (15)0.0413 (15)0.0011 (12)0.0073 (13)0.0006 (12)
C120.0392 (16)0.0365 (15)0.0402 (16)0.0010 (12)0.0026 (13)0.0054 (12)
C130.0333 (14)0.0413 (16)0.0400 (14)0.0018 (12)0.0035 (14)0.0014 (12)
C140.0432 (17)0.0286 (14)0.0465 (17)0.0015 (12)0.0057 (14)0.0002 (12)
C150.0366 (17)0.0337 (15)0.0381 (16)0.0000 (13)0.0048 (13)0.0041 (12)
C160.0546 (17)0.0449 (16)0.059 (2)0.0013 (13)0.016 (2)0.009 (2)
C170.068 (3)0.0340 (17)0.066 (2)0.0039 (16)0.011 (2)0.0100 (15)
Geometric parameters (Å, º) top
I1—C122.091 (3)C6—C71.462 (7)
O1—C91.262 (4)C7—C81.316 (6)
O2—C111.344 (4)C7—H70.9300
O2—H2o0.85 (1)C8—C91.462 (5)
O3—C131.336 (5)C8—H80.9300
O3—C161.416 (4)C9—C101.469 (5)
O4—C151.352 (4)C10—C111.416 (4)
O4—C171.436 (4)C10—C151.432 (5)
C1—C61.387 (5)C11—C121.392 (5)
C1—C21.390 (6)C12—C131.383 (5)
C1—H10.9300C13—C141.401 (5)
C2—C31.363 (7)C14—C151.377 (5)
C2—H20.9300C14—H140.9300
C3—C41.378 (7)C16—H16a0.9600
C3—H30.9300C16—H16b0.9600
C4—C51.372 (6)C16—H16c0.9600
C4—H40.9300C17—H17a0.9600
C5—C61.388 (5)C17—H17b0.9600
C5—H50.9300C17—H17c0.9600
C11—O2—H2o98 (4)C11—C10—C15116.4 (3)
C13—O3—C16120.2 (4)C11—C10—C9118.3 (3)
C15—O4—C17118.8 (3)C15—C10—C9125.2 (3)
C6—C1—C2121.1 (4)O2—C11—C12117.0 (3)
C6—C1—H1119.4O2—C11—C10121.1 (3)
C2—C1—H1119.4C12—C11—C10122.0 (3)
C3—C2—C1119.2 (4)C13—C12—C11119.9 (3)
C3—C2—H2120.4C13—C12—I1120.6 (2)
C1—C2—H2120.4C11—C12—I1119.5 (2)
C2—C3—C4120.5 (4)O3—C13—C12117.2 (3)
C2—C3—H3119.7O3—C13—C14122.9 (3)
C4—C3—H3119.7C12—C13—C14119.9 (3)
C5—C4—C3120.5 (4)C15—C14—C13120.5 (3)
C5—C4—H4119.7C15—C14—H14119.7
C3—C4—H4119.7C13—C14—H14119.7
C4—C5—C6120.2 (4)O4—C15—C14122.1 (3)
C4—C5—H5119.9O4—C15—C10116.7 (3)
C6—C5—H5119.9C14—C15—C10121.2 (3)
C1—C6—C5118.4 (4)O3—C16—H16a109.5
C1—C6—C7118.2 (3)O3—C16—H16b109.5
C5—C6—C7123.3 (3)H16a—C16—H16b109.5
C8—C7—C6128.3 (3)O3—C16—H16c109.5
C8—C7—H7115.9H16a—C16—H16c109.5
C6—C7—H7115.9H16b—C16—H16c109.5
C7—C8—C9120.9 (3)O4—C17—H17a109.5
C7—C8—H8119.5O4—C17—H17b109.5
C9—C8—H8119.5H17a—C17—H17b109.5
O1—C9—C8117.4 (3)O4—C17—H17c109.5
O1—C9—C10118.5 (3)H17a—C17—H17c109.5
C8—C9—C10124.1 (3)H17b—C17—H17c109.5
C6—C1—C2—C31.3 (8)O2—C11—C12—C13178.5 (3)
C1—C2—C3—C40.7 (8)C10—C11—C12—C131.5 (5)
C2—C3—C4—C50.1 (8)O2—C11—C12—I10.7 (4)
C3—C4—C5—C60.4 (8)C10—C11—C12—I1179.4 (2)
C2—C1—C6—C51.0 (7)C16—O3—C13—C12175.6 (4)
C2—C1—C6—C7179.4 (4)C16—O3—C13—C143.6 (6)
C4—C5—C6—C10.2 (6)C11—C12—C13—O3179.3 (3)
C4—C5—C6—C7178.5 (4)I1—C12—C13—O30.2 (4)
C1—C6—C7—C8173.1 (4)C11—C12—C13—C140.2 (5)
C5—C6—C7—C85.2 (7)I1—C12—C13—C14179.0 (2)
C6—C7—C8—C9178.9 (4)O3—C13—C14—C15179.8 (3)
C7—C8—C9—O13.3 (6)C12—C13—C14—C150.7 (5)
C7—C8—C9—C10178.6 (4)C17—O4—C15—C141.4 (5)
O1—C9—C10—C112.5 (5)C17—O4—C15—C10179.8 (3)
C8—C9—C10—C11175.5 (3)C13—C14—C15—O4178.3 (3)
O1—C9—C10—C15174.3 (3)C13—C14—C15—C100.4 (5)
C8—C9—C10—C157.7 (5)C11—C10—C15—O4176.8 (3)
C15—C10—C11—O2177.5 (3)C9—C10—C15—O40.0 (5)
C9—C10—C11—O20.4 (5)C11—C10—C15—C141.9 (5)
C15—C10—C11—C122.4 (5)C9—C10—C15—C14178.8 (3)
C9—C10—C11—C12179.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2o···O10.85 (1)1.61 (2)2.434 (4)163 (5)
 

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