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In the title biologically active compound, C16H12O3, the central C=C double bond is trans configured. The mol­ecule consists of two essentially planar parts which are twisted by 26.89 (5)° with respect to each other.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602767X/lh2140sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680602767X/lh2140Isup2.hkl
Contains datablock I

CCDC reference: 621402

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C)= 0.001 Å
  • R factor = 0.034
  • wR factor = 0.092
  • Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

3-(1,3-Benzodioxol-5-yl)-1-phenylprop-2-en-1-one top
Crystal data top
C16H12O3F(000) = 1056
Mr = 252.26Dx = 1.366 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 31874 reflections
a = 11.1234 (5) Åθ = 2.0–27.6°
b = 7.7504 (4) ŵ = 0.09 mm1
c = 28.4607 (11) ÅT = 173 K
V = 2453.62 (19) Å3Plate, light yellow
Z = 80.38 × 0.21 × 0.19 mm
Data collection top
Stoe IPDS-II two-circle
diffractometer
2590 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.049
Graphite monochromatorθmax = 27.6°, θmin = 2.3°
ω scansh = 1414
31874 measured reflectionsk = 1010
2813 independent reflectionsl = 3636
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)] = 0.035H-atom parameters constrained
wR(F2) = 0.092 w = 1/[σ2(Fo2) + (0.0462P)2 + 0.6049P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2813 reflectionsΔρmax = 0.22 e Å3
173 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.033 (2)
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
O10.56812 (7)0.05686 (10)0.63073 (3)0.0363 (2)
C10.45954 (10)0.15656 (14)0.63644 (4)0.0340 (2)
H1A0.39070.07930.64290.041*
H1B0.46820.23770.66310.041*
O20.43962 (7)0.25004 (11)0.59360 (3)0.0391 (2)
C20.52444 (8)0.19228 (12)0.56250 (3)0.0269 (2)
C30.60188 (9)0.07718 (13)0.58481 (3)0.0276 (2)
C40.69577 (9)0.00043 (13)0.56137 (4)0.0307 (2)
H40.74890.07750.57660.037*
C50.70899 (9)0.04319 (13)0.51383 (4)0.0288 (2)
H50.77340.00660.49660.035*
C60.63092 (8)0.15649 (12)0.49070 (3)0.0256 (2)
C70.53550 (8)0.23432 (12)0.51598 (3)0.0272 (2)
H70.48150.31240.50130.033*
C80.64970 (9)0.18650 (12)0.44061 (3)0.0277 (2)
H80.71700.13040.42690.033*
C90.58293 (9)0.28406 (13)0.41180 (3)0.0296 (2)
H90.51600.34580.42390.036*
C100.61277 (9)0.29620 (13)0.36127 (3)0.0286 (2)
O100.70294 (7)0.22721 (11)0.34492 (3)0.0378 (2)
C110.52988 (9)0.39305 (12)0.32942 (3)0.0275 (2)
C120.57721 (10)0.46311 (13)0.28818 (4)0.0314 (2)
H120.66060.45160.28160.038*
C130.50333 (11)0.54935 (14)0.25671 (4)0.0360 (2)
H130.53630.59770.22890.043*
C140.38143 (11)0.56497 (16)0.26584 (4)0.0394 (3)
H140.33090.62410.24430.047*
C150.33311 (10)0.49431 (17)0.30647 (4)0.0419 (3)
H150.24930.50370.31250.050*
C160.40713 (9)0.40980 (15)0.33840 (4)0.0345 (2)
H160.37400.36330.36640.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0388 (4)0.0439 (4)0.0261 (4)0.0072 (3)0.0019 (3)0.0043 (3)
C10.0425 (6)0.0321 (5)0.0275 (5)0.0046 (4)0.0015 (4)0.0001 (4)
O20.0390 (4)0.0491 (5)0.0290 (4)0.0154 (4)0.0041 (3)0.0051 (3)
C20.0253 (4)0.0266 (4)0.0288 (5)0.0005 (3)0.0019 (3)0.0021 (4)
C30.0301 (5)0.0271 (5)0.0255 (4)0.0025 (4)0.0047 (4)0.0010 (3)
C40.0307 (5)0.0277 (5)0.0338 (5)0.0043 (4)0.0059 (4)0.0031 (4)
C50.0274 (4)0.0261 (5)0.0328 (5)0.0022 (4)0.0009 (4)0.0016 (4)
C60.0261 (4)0.0226 (4)0.0282 (5)0.0034 (3)0.0025 (3)0.0005 (3)
C70.0268 (4)0.0257 (4)0.0291 (5)0.0016 (3)0.0037 (4)0.0020 (4)
C80.0278 (4)0.0264 (4)0.0290 (5)0.0036 (3)0.0002 (4)0.0020 (4)
C90.0320 (5)0.0304 (5)0.0265 (5)0.0002 (4)0.0008 (4)0.0008 (4)
C100.0294 (5)0.0289 (4)0.0275 (5)0.0034 (4)0.0000 (4)0.0016 (4)
O100.0342 (4)0.0471 (5)0.0323 (4)0.0058 (3)0.0029 (3)0.0007 (3)
C110.0316 (5)0.0271 (5)0.0240 (4)0.0036 (4)0.0003 (4)0.0019 (4)
C120.0348 (5)0.0308 (5)0.0287 (5)0.0032 (4)0.0045 (4)0.0004 (4)
C130.0458 (6)0.0355 (5)0.0267 (5)0.0048 (4)0.0021 (4)0.0047 (4)
C140.0409 (6)0.0427 (6)0.0347 (6)0.0046 (5)0.0089 (5)0.0077 (5)
C150.0301 (5)0.0541 (7)0.0416 (6)0.0030 (5)0.0026 (4)0.0099 (5)
C160.0316 (5)0.0426 (6)0.0294 (5)0.0038 (4)0.0024 (4)0.0055 (4)
Geometric parameters (Å, º) top
O1—C31.3689 (12)C8—H80.9500
O1—C11.4430 (13)C9—C101.4788 (13)
C1—O21.4355 (13)C9—H90.9500
C1—H1A0.9900C10—O101.2283 (12)
C1—H1B0.9900C10—C111.4951 (14)
O2—C21.3688 (12)C11—C161.3952 (14)
C2—C71.3692 (14)C11—C121.3962 (13)
C2—C31.3931 (13)C12—C131.3873 (15)
C3—C41.3746 (14)C12—H120.9500
C4—C51.4009 (14)C13—C141.3860 (17)
C4—H40.9500C13—H130.9500
C5—C61.3995 (13)C14—C151.3878 (16)
C5—H50.9500C14—H140.9500
C6—C71.4171 (13)C15—C161.3902 (15)
C6—C81.4594 (13)C15—H150.9500
C7—H70.9500C16—H160.9500
C8—C91.3401 (14)
C3—O1—C1105.99 (7)C9—C8—H8116.3
O2—C1—O1107.68 (8)C6—C8—H8116.3
O2—C1—H1A110.2C8—C9—C10120.43 (9)
O1—C1—H1A110.2C8—C9—H9119.8
O2—C1—H1B110.2C10—C9—H9119.8
O1—C1—H1B110.2O10—C10—C9121.61 (9)
H1A—C1—H1B108.5O10—C10—C11119.50 (9)
C2—O2—C1106.12 (8)C9—C10—C11118.89 (9)
O2—C2—C7127.54 (9)C16—C11—C12119.13 (9)
O2—C2—C3109.94 (8)C16—C11—C10122.63 (9)
C7—C2—C3122.51 (9)C12—C11—C10118.19 (9)
O1—C3—C4128.45 (9)C13—C12—C11120.45 (10)
O1—C3—C2109.82 (8)C13—C12—H12119.8
C4—C3—C2121.73 (9)C11—C12—H12119.8
C3—C4—C5116.49 (9)C14—C13—C12120.04 (10)
C3—C4—H4121.8C14—C13—H13120.0
C5—C4—H4121.8C12—C13—H13120.0
C6—C5—C4122.53 (9)C13—C14—C15120.04 (10)
C6—C5—H5118.7C13—C14—H14120.0
C4—C5—H5118.7C15—C14—H14120.0
C5—C6—C7119.54 (9)C14—C15—C16120.08 (11)
C5—C6—C8118.08 (9)C14—C15—H15120.0
C7—C6—C8122.36 (9)C16—C15—H15120.0
C2—C7—C6117.19 (9)C15—C16—C11120.25 (10)
C2—C7—H7121.4C15—C16—H16119.9
C6—C7—H7121.4C11—C16—H16119.9
C9—C8—C6127.47 (9)
C3—O1—C1—O26.28 (11)C8—C6—C7—C2177.94 (9)
O1—C1—O2—C26.60 (11)C5—C6—C8—C9177.25 (10)
C1—O2—C2—C7174.71 (10)C7—C6—C8—C91.18 (16)
C1—O2—C2—C34.46 (11)C6—C8—C9—C10178.11 (9)
C1—O1—C3—C4176.03 (10)C8—C9—C10—O104.72 (15)
C1—O1—C3—C23.61 (11)C8—C9—C10—C11174.45 (9)
O2—C2—C3—O10.53 (12)O10—C10—C11—C16151.40 (11)
C7—C2—C3—O1178.68 (9)C9—C10—C11—C1627.79 (14)
O2—C2—C3—C4179.80 (9)O10—C10—C11—C1225.96 (14)
C7—C2—C3—C40.99 (15)C9—C10—C11—C12154.85 (9)
O1—C3—C4—C5179.20 (10)C16—C11—C12—C130.47 (15)
C2—C3—C4—C50.40 (15)C10—C11—C12—C13177.93 (9)
C3—C4—C5—C60.61 (15)C11—C12—C13—C140.66 (17)
C4—C5—C6—C71.06 (15)C12—C13—C14—C150.02 (18)
C4—C5—C6—C8177.42 (9)C13—C14—C15—C160.88 (19)
O2—C2—C7—C6179.58 (9)C14—C15—C16—C111.06 (18)
C3—C2—C7—C60.52 (14)C12—C11—C16—C150.39 (16)
C5—C6—C7—C20.47 (14)C10—C11—C16—C15176.95 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O10i0.992.593.0397 (14)107
Symmetry code: (i) x1/2, y+1/2, z+1.
 

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