(E)-3-(1,3-Benzodioxol-5-yl)-1-(2-hydr­oxy-4,6-dimethoxy­phen­yl)prop-2-en-1-one

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—H...O hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.102
• Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.724     1.000
            Tmin(prime) and Tmax expected:      0.956     0.978
            RR(prime) =      0.741
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.74

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1

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           27.30
           From the CIF: _reflns_number_total               2031
           Count of symmetry unique reflns         2042
           Completeness (_total/calc)             99.46%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 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
   2 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

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Computing details

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

Crystal data

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) Å^3	Block, colourless
Z = 4	0.4 × 0.3 × 0.2 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0667P)^2 + 0.1168P] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O2^i	0.93	2.53	3.443 (2)	166

Symmetry code: (i) −x+1/2, −y+2, z+1/2.