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The title compound, C17H14O4, shows satisfactory cytotoxic activity against Artemia salina. Two non-classical inter­molecular C—H...O hydrogen bonds [C...O = 3.273 (2) and 3.302 (3) Å] join the mol­ecules alternately head-to-head and tail-to-tail across crystallographic inversion centres, resulting in a linear chain along the [1\overline{4}1] direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806004600/bh6062sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806004600/bh6062Isup2.hkl
Contains datablock I

CCDC reference: 601111

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.061
  • wR factor = 0.165
  • Data-to-parameter ratio = 11.2

checkCIF/PLATON results

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Computing details top

Data collection: CAD-4-PC Software (Enraf–Nonius, 1993); cell refinement: CAD-4-PC Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-(1,3-Benzodioxol-5-yl)-1-(4-methoxyphenyl)prop-2-enone top
Crystal data top
C17H14O4Z = 2
Mr = 282.28F(000) = 296
Triclinic, P1Dx = 1.408 Mg m3
Hall symbol: -P 1Melting point: 403 K
a = 6.0987 (9) ÅCu Kα radiation, λ = 1.54180 Å
b = 7.463 (1) ÅCell parameters from 25 reflections
c = 14.932 (1) Åθ = 18.1–44.5°
α = 84.18 (1)°µ = 0.83 mm1
β = 89.65 (1)°T = 297 K
γ = 79.90 (1)°Block, yellow
V = 665.60 (14) Å30.35 × 0.35 × 0.28 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.009
Radiation source: fine-focus sealed tubeθmax = 67.1°, θmin = 3.0°
Graphite monochromatorh = 77
non–profiled ω/2θ scansk = 88
2435 measured reflectionsl = 017
2343 independent reflections2 standard reflections every 120 min
2234 reflections with I > 2σ(I) intensity decay: <1%
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)] = 0.061H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.165 w = 1/[σ2(Fo2) + (0.1073P)2 + 0.1215P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max < 0.001
2343 reflectionsΔρmax = 0.41 e Å3
209 parametersΔρmin = 0.41 e Å3
11 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.330 (19)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3263 (2)0.5494 (2)0.23385 (11)0.0670 (5)
O21.3626 (2)0.25012 (17)0.46011 (10)0.0551 (4)
O31.0340 (2)0.33470 (16)0.41804 (9)0.0537 (4)
O40.5728 (2)1.29225 (18)0.06029 (10)0.0597 (4)
C10.3568 (3)0.9172 (3)0.17773 (12)0.0499 (5)
H10.22200.89690.20250.060*
C20.3735 (3)1.0871 (3)0.13780 (13)0.0530 (5)
H20.25141.18150.13660.064*
C30.5735 (3)1.1194 (2)0.09884 (11)0.0458 (5)
C40.7563 (3)0.9786 (3)0.10271 (12)0.0492 (5)
H40.89010.99860.07680.059*
C50.7382 (3)0.8082 (2)0.14543 (12)0.0478 (5)
H50.86240.71530.14960.057*
C60.5383 (3)0.7733 (2)0.18211 (11)0.0440 (5)
C70.5113 (3)0.5912 (3)0.22631 (12)0.0480 (5)
C80.7123 (3)0.4654 (2)0.26370 (12)0.0494 (5)
H80.84500.50940.26790.059*
C90.7077 (3)0.2910 (2)0.29138 (11)0.0443 (5)
H90.582 (4)0.247 (3)0.2847 (14)0.053*
C100.8895 (3)0.1549 (2)0.33402 (10)0.0406 (4)
C111.0881 (3)0.2027 (2)0.36024 (11)0.0444 (5)
H111.10810.32340.34790.053*
C121.2580 (3)0.0760 (2)0.40428 (11)0.0451 (5)
H121.38900.10980.42270.054*
C131.2229 (3)0.1014 (2)0.41925 (11)0.0411 (4)
C141.0272 (3)0.1510 (2)0.39307 (11)0.0404 (4)
C150.8570 (3)0.0278 (2)0.35116 (11)0.0421 (4)
H150.72530.06300.33470.050*
C161.2485 (3)0.4011 (2)0.45760 (15)0.0520 (5)
H16A1.234 (4)0.459 (3)0.5164 (13)0.062*
H16B1.326 (3)0.487 (3)0.4160 (13)0.062*
C170.7716 (4)1.3366 (3)0.02238 (17)0.0661 (6)
H17A0.729 (5)1.467 (3)0.0020 (19)0.099*
H17B0.884 (5)1.329 (4)0.0679 (17)0.099*
H17C0.805 (5)1.262 (4)0.0227 (17)0.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0476 (8)0.0629 (9)0.0889 (11)0.0157 (6)0.0006 (7)0.0100 (7)
O20.0466 (7)0.0410 (7)0.0770 (9)0.0104 (5)0.0121 (6)0.0031 (6)
O30.0486 (7)0.0345 (7)0.0788 (9)0.0126 (5)0.0068 (6)0.0001 (6)
O40.0555 (8)0.0453 (8)0.0703 (9)0.0028 (6)0.0001 (6)0.0117 (6)
C10.0364 (9)0.0594 (11)0.0513 (10)0.0044 (7)0.0022 (7)0.0003 (8)
C20.0419 (9)0.0513 (10)0.0600 (11)0.0045 (7)0.0041 (8)0.0006 (8)
C30.0469 (9)0.0441 (9)0.0429 (9)0.0020 (7)0.0052 (7)0.0015 (7)
C40.0461 (10)0.0465 (10)0.0512 (9)0.0022 (7)0.0056 (7)0.0021 (7)
C50.0432 (9)0.0429 (9)0.0529 (10)0.0012 (7)0.0024 (7)0.0007 (7)
C60.0422 (9)0.0462 (10)0.0423 (8)0.0057 (7)0.0047 (7)0.0020 (7)
C70.0448 (10)0.0501 (10)0.0489 (9)0.0106 (8)0.0005 (7)0.0009 (7)
C80.0486 (10)0.0458 (10)0.0534 (10)0.0116 (8)0.0057 (8)0.0040 (7)
C90.0432 (9)0.0462 (10)0.0446 (9)0.0122 (7)0.0008 (7)0.0031 (7)
C100.0443 (9)0.0395 (9)0.0393 (8)0.0107 (7)0.0025 (6)0.0039 (6)
C110.0492 (10)0.0368 (9)0.0499 (9)0.0161 (7)0.0010 (7)0.0022 (7)
C120.0418 (9)0.0452 (10)0.0516 (9)0.0171 (7)0.0022 (7)0.0041 (7)
C130.0401 (9)0.0397 (9)0.0444 (8)0.0095 (6)0.0003 (6)0.0036 (6)
C140.0443 (9)0.0336 (8)0.0455 (8)0.0126 (6)0.0049 (6)0.0048 (6)
C150.0400 (9)0.0416 (9)0.0478 (9)0.0145 (7)0.0022 (7)0.0075 (7)
C160.0463 (10)0.0417 (10)0.0678 (11)0.0106 (8)0.0063 (8)0.0002 (8)
C170.0614 (13)0.0511 (12)0.0801 (14)0.0062 (9)0.0039 (11)0.0145 (10)
Geometric parameters (Å, º) top
O1—C71.224 (2)C8—C91.330 (3)
O2—C131.367 (2)C8—H80.9300
O2—C161.428 (2)C9—C101.466 (2)
O3—C141.377 (2)C9—H90.89 (2)
O3—C161.424 (2)C10—C111.390 (2)
O4—C31.358 (2)C10—C151.410 (2)
O4—C171.412 (3)C11—C121.393 (2)
C1—C21.366 (3)C11—H110.9300
C1—C61.397 (2)C12—C131.374 (2)
C1—H10.9300C12—H120.9300
C2—C31.396 (3)C13—C141.380 (2)
C2—H20.9300C14—C151.368 (2)
C3—C41.388 (2)C15—H150.9300
C4—C51.386 (3)C16—H16A0.95 (2)
C4—H40.9300C16—H16B0.996 (18)
C5—C61.389 (2)C17—H17A0.99 (2)
C5—H50.9300C17—H17B0.96 (2)
C6—C71.485 (2)C17—H17C0.92 (2)
C7—C81.481 (3)
C13—O2—C16105.84 (13)C11—C10—C15119.73 (16)
C14—O3—C16105.91 (13)C11—C10—C9121.79 (15)
C3—O4—C17118.84 (15)C15—C10—C9118.46 (15)
C2—C1—C6121.32 (17)C10—C11—C12122.24 (15)
C2—C1—H1119.3C10—C11—H11118.9
C6—C1—H1119.3C12—C11—H11118.9
C1—C2—C3120.15 (16)C13—C12—C11116.80 (15)
C1—C2—H2119.9C13—C12—H12121.6
C3—C2—H2119.9C11—C12—H12121.6
O4—C3—C4124.78 (17)O2—C13—C12128.15 (15)
O4—C3—C2115.70 (15)O2—C13—C14110.28 (15)
C4—C3—C2119.51 (16)C12—C13—C14121.56 (16)
C5—C4—C3119.62 (17)C15—C14—O3128.06 (15)
C5—C4—H4120.2C15—C14—C13122.42 (15)
C3—C4—H4120.2O3—C14—C13109.49 (15)
C4—C5—C6121.28 (16)C14—C15—C10117.23 (15)
C4—C5—H5119.4C14—C15—H15121.4
C6—C5—H5119.4C10—C15—H15121.4
C5—C6—C1118.07 (16)O3—C16—O2108.37 (14)
C5—C6—C7122.75 (16)O3—C16—H16A110.1 (14)
C1—C6—C7119.18 (16)O2—C16—H16A110.9 (14)
O1—C7—C8121.25 (17)O3—C16—H16B105.0 (12)
O1—C7—C6120.43 (17)O2—C16—H16B109.9 (13)
C8—C7—C6118.28 (16)H16A—C16—H16B112.3 (17)
C9—C8—C7121.63 (17)O4—C17—H17A103.8 (16)
C9—C8—H8119.2O4—C17—H17B111.1 (18)
C7—C8—H8119.2H17A—C17—H17B108 (2)
C8—C9—C10127.33 (17)O4—C17—H17C105.1 (19)
C8—C9—H9119.4 (14)H17A—C17—H17C112 (2)
C10—C9—H9113.2 (14)H17B—C17—H17C117 (2)
C6—C1—C2—C31.1 (3)C8—C9—C10—C15174.40 (16)
C17—O4—C3—C41.3 (3)C15—C10—C11—C120.7 (3)
C17—O4—C3—C2177.78 (18)C9—C10—C11—C12177.18 (15)
C1—C2—C3—O4179.53 (16)C10—C11—C12—C131.4 (3)
C1—C2—C3—C41.4 (3)C16—O2—C13—C12179.35 (18)
O4—C3—C4—C5178.79 (15)C16—O2—C13—C141.09 (19)
C2—C3—C4—C50.2 (3)C11—C12—C13—O2179.55 (15)
C3—C4—C5—C62.1 (3)C11—C12—C13—C140.9 (3)
C4—C5—C6—C12.3 (3)C16—O3—C14—C15179.06 (17)
C4—C5—C6—C7178.43 (15)C16—O3—C14—C132.72 (19)
C2—C1—C6—C50.7 (3)O2—C13—C14—C15179.39 (14)
C2—C1—C6—C7179.98 (16)C12—C13—C14—C150.2 (3)
C5—C6—C7—O1158.42 (18)O2—C13—C14—O31.05 (19)
C1—C6—C7—O122.3 (3)C12—C13—C14—O3178.55 (14)
C5—C6—C7—C823.8 (2)O3—C14—C15—C10178.92 (14)
C1—C6—C7—C8155.45 (17)C13—C14—C15—C100.9 (3)
O1—C7—C8—C912.9 (3)C11—C10—C15—C140.4 (2)
C6—C7—C8—C9169.29 (16)C9—C10—C15—C14178.40 (13)
C7—C8—C9—C10176.36 (15)C14—O3—C16—O23.4 (2)
C8—C9—C10—C117.7 (3)C13—O2—C16—O32.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16A···O3i0.95 (2)2.56 (2)3.273 (2)132 (2)
C17—H17A···O4ii0.99 (2)2.43 (3)3.302 (3)146 (2)
Symmetry codes: (i) x+2, y1, z+1; (ii) x+1, y+3, z.
 

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