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The molecule of the title compound, C13H10O2 is nearly planar; the furyl and and phenyl rings are only slightly twisted with respect to each other, making a dihedral angle of 8.56 (6)°. The crystal structure is stabilized by weak intermolecular C—H...O contacts and C—H...π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805010615/dn6214sup1.cif
Contains datablocks samalt2-10, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805010615/dn6214Isup2.hkl
Contains datablock I

CCDC reference: 257527

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.040
  • wR factor = 0.079
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C12 - C13 .. 8.32 su
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.80 mm PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C13 .. 5.22 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C6 - C7 .. 6.60 su
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA Stoe & Cie, 2002; cell refinement: X-AREA; data reduction: X-RED32 Stoe & Cie, 2002; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-III (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997); PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

1-(2-furyl)-3-phenyl-2-propen-1-one top
Crystal data top
C13H10O2F(000) = 832
Mr = 198.21Dx = 1.270 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 12064 reflections
a = 10.4874 (10) Åθ = 1.7–29.1°
b = 12.1216 (14) ŵ = 0.09 mm1
c = 16.3091 (16) ÅT = 293 K
V = 2073.3 (4) Å3Plate, colourless
Z = 80.80 × 0.47 × 0.09 mm
Data collection top
STOE IPDS 2
diffractometer
2034 independent reflections
Radiation source: fine-focus sealed tube1020 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.100
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.5°
ω scansh = 1212
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1414
Tmin = 0.942, Tmax = 0.989l = 2020
13565 measured reflections
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)] = 0.040H-atom parameters constrained
wR(F2) = 0.079 w = 1/[σ2(Fo2) + (0.0327P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.84(Δ/σ)max < 0.001
2034 reflectionsΔρmax = 0.12 e Å3
137 parametersΔρmin = 0.13 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0154 (12)
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
C10.20381 (18)0.60643 (15)0.62210 (11)0.0647 (5)
H10.11870.61360.60700.078*
C20.2559 (2)0.68105 (16)0.67614 (12)0.0747 (6)
H20.20610.73760.69760.090*
C30.3816 (2)0.67153 (18)0.69808 (13)0.0790 (6)
H30.41720.72120.73500.095*
C40.45488 (18)0.58827 (17)0.66530 (13)0.0775 (6)
H40.54060.58300.67940.093*
C50.40303 (17)0.51287 (16)0.61194 (11)0.0655 (5)
H50.45340.45660.59070.079*
C60.27555 (16)0.52057 (15)0.58962 (10)0.0551 (5)
C70.21484 (16)0.44182 (16)0.53447 (10)0.0611 (5)
H70.12980.45570.52210.073*
C80.26491 (16)0.35295 (16)0.49966 (10)0.0602 (5)
H80.35030.33670.50930.072*
C90.19053 (16)0.27911 (16)0.44638 (10)0.0608 (5)
C100.26210 (15)0.19662 (15)0.40163 (10)0.0552 (5)
C110.38618 (16)0.16970 (16)0.39844 (11)0.0640 (5)
H110.45170.20200.42850.077*
C120.39871 (18)0.08397 (17)0.34148 (12)0.0750 (6)
H120.47380.04850.32650.090*
C130.2832 (2)0.06328 (17)0.31323 (12)0.0763 (6)
H130.26440.00980.27420.092*
O10.07453 (11)0.28654 (13)0.43924 (8)0.0906 (5)
O20.19553 (11)0.13029 (11)0.34873 (8)0.0721 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0635 (11)0.0596 (12)0.0711 (13)0.0104 (10)0.0046 (10)0.0096 (11)
C20.0856 (15)0.0541 (13)0.0842 (15)0.0070 (11)0.0162 (12)0.0047 (12)
C30.0856 (15)0.0692 (15)0.0823 (15)0.0143 (13)0.0090 (13)0.0073 (12)
C40.0623 (12)0.0841 (16)0.0862 (15)0.0053 (12)0.0036 (11)0.0043 (14)
C50.0595 (11)0.0698 (13)0.0672 (13)0.0048 (10)0.0059 (10)0.0038 (11)
C60.0574 (12)0.0557 (11)0.0521 (11)0.0045 (9)0.0043 (9)0.0075 (9)
C70.0521 (10)0.0725 (13)0.0587 (11)0.0087 (10)0.0015 (9)0.0107 (10)
C80.0495 (10)0.0718 (13)0.0593 (11)0.0085 (10)0.0013 (9)0.0029 (10)
C90.0483 (10)0.0793 (14)0.0548 (11)0.0013 (10)0.0006 (9)0.0022 (11)
C100.0513 (9)0.0655 (12)0.0488 (10)0.0033 (10)0.0013 (9)0.0005 (9)
C110.0560 (11)0.0721 (14)0.0640 (12)0.0021 (10)0.0036 (10)0.0078 (11)
C120.0626 (12)0.0818 (15)0.0804 (14)0.0101 (11)0.0000 (11)0.0139 (13)
C130.0822 (14)0.0736 (14)0.0732 (14)0.0002 (12)0.0084 (12)0.0175 (11)
O10.0492 (7)0.1257 (13)0.0971 (10)0.0116 (8)0.0048 (7)0.0287 (10)
O20.0595 (7)0.0849 (9)0.0719 (9)0.0080 (7)0.0036 (7)0.0142 (8)
Geometric parameters (Å, º) top
C1—C21.376 (2)C7—H70.9300
C1—C61.389 (2)C8—C91.471 (2)
C1—H10.9300C8—H80.9300
C2—C31.371 (3)C9—O11.2254 (18)
C2—H20.9300C9—C101.448 (2)
C3—C41.377 (3)C10—C111.343 (2)
C3—H30.9300C10—O21.3705 (19)
C4—C51.374 (2)C11—C121.400 (2)
C4—H40.9300C11—H110.9300
C5—C61.389 (2)C12—C131.320 (2)
C5—H50.9300C12—H120.9300
C6—C71.458 (2)C13—O21.357 (2)
C7—C81.326 (2)C13—H130.9300
C2—C1—C6121.46 (18)C6—C7—H7115.7
C2—C1—H1119.3C7—C8—C9122.49 (17)
C6—C1—H1119.3C7—C8—H8118.8
C3—C2—C1119.6 (2)C9—C8—H8118.8
C3—C2—H2120.2O1—C9—C10121.18 (18)
C1—C2—H2120.2O1—C9—C8122.52 (18)
C2—C3—C4119.8 (2)C10—C9—C8116.30 (15)
C2—C3—H3120.1C11—C10—O2109.07 (16)
C4—C3—H3120.1C11—C10—C9133.63 (17)
C5—C4—C3120.82 (19)O2—C10—C9117.29 (15)
C5—C4—H4119.6C10—C11—C12107.29 (17)
C3—C4—H4119.6C10—C11—H11126.4
C4—C5—C6120.15 (18)C12—C11—H11126.4
C4—C5—H5119.9C13—C12—C11106.64 (17)
C6—C5—H5119.9C13—C12—H12126.7
C5—C6—C1118.15 (18)C11—C12—H12126.7
C5—C6—C7122.56 (17)C12—C13—O2111.06 (17)
C1—C6—C7119.29 (17)C12—C13—H13124.5
C8—C7—C6128.54 (17)O2—C13—H13124.5
C8—C7—H7115.7C13—O2—C10105.95 (14)
C6—C1—C2—C30.6 (3)C7—C8—C9—C10169.79 (16)
C1—C2—C3—C40.7 (3)O1—C9—C10—C11179.2 (2)
C2—C3—C4—C51.3 (3)C8—C9—C10—C111.3 (3)
C3—C4—C5—C60.7 (3)O1—C9—C10—O22.5 (3)
C4—C5—C6—C10.5 (3)C8—C9—C10—O2177.05 (15)
C4—C5—C6—C7178.85 (16)O2—C10—C11—C120.3 (2)
C2—C1—C6—C51.2 (2)C9—C10—C11—C12178.19 (18)
C2—C1—C6—C7178.21 (16)C10—C11—C12—C130.0 (2)
C5—C6—C7—C82.0 (3)C11—C12—C13—O20.3 (2)
C1—C6—C7—C8177.42 (17)C12—C13—O2—C100.4 (2)
C6—C7—C8—C9178.54 (16)C11—C10—O2—C130.41 (19)
C7—C8—C9—O19.7 (3)C9—C10—O2—C13178.32 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O1i0.932.483.347 (2)156
C11—H11···O1ii0.932.523.345 (2)149
C13—H13···Cg2iii0.932.583.410 (2)149
Symmetry codes: (i) x, y+1, z+1; (ii) x+1/2, y+1/2, z+1; (iii) x, y1/2, z3/2.
 

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