The molecule of the title compound, C
13H
10O
2 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
CCDC reference: 257527
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
C13H10O2 | F(000) = 832 |
Mr = 198.21 | Dx = 1.270 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 12064 reflections |
a = 10.4874 (10) Å | θ = 1.7–29.1° |
b = 12.1216 (14) Å | µ = 0.09 mm−1 |
c = 16.3091 (16) Å | T = 293 K |
V = 2073.3 (4) Å3 | Plate, colourless |
Z = 8 | 0.80 × 0.47 × 0.09 mm |
Data collection top
STOE IPDS 2 diffractometer | 2034 independent reflections |
Radiation source: fine-focus sealed tube | 1020 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.100 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.5° |
ω scans | h = −12→12 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −14→14 |
Tmin = 0.942, Tmax = 0.989 | l = −20→20 |
13565 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-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 reflections | Δρmax = 0.12 e Å−3 |
137 parameters | Δρmin = −0.13 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
C1 | 0.20381 (18) | 0.60643 (15) | 0.62210 (11) | 0.0647 (5) | |
H1 | 0.1187 | 0.6136 | 0.6070 | 0.078* | |
C2 | 0.2559 (2) | 0.68105 (16) | 0.67614 (12) | 0.0747 (6) | |
H2 | 0.2061 | 0.7376 | 0.6976 | 0.090* | |
C3 | 0.3816 (2) | 0.67153 (18) | 0.69808 (13) | 0.0790 (6) | |
H3 | 0.4172 | 0.7212 | 0.7350 | 0.095* | |
C4 | 0.45488 (18) | 0.58827 (17) | 0.66530 (13) | 0.0775 (6) | |
H4 | 0.5406 | 0.5830 | 0.6794 | 0.093* | |
C5 | 0.40303 (17) | 0.51287 (16) | 0.61194 (11) | 0.0655 (5) | |
H5 | 0.4534 | 0.4566 | 0.5907 | 0.079* | |
C6 | 0.27555 (16) | 0.52057 (15) | 0.58962 (10) | 0.0551 (5) | |
C7 | 0.21484 (16) | 0.44182 (16) | 0.53447 (10) | 0.0611 (5) | |
H7 | 0.1298 | 0.4557 | 0.5221 | 0.073* | |
C8 | 0.26491 (16) | 0.35295 (16) | 0.49966 (10) | 0.0602 (5) | |
H8 | 0.3503 | 0.3367 | 0.5093 | 0.072* | |
C9 | 0.19053 (16) | 0.27911 (16) | 0.44638 (10) | 0.0608 (5) | |
C10 | 0.26210 (15) | 0.19662 (15) | 0.40163 (10) | 0.0552 (5) | |
C11 | 0.38618 (16) | 0.16970 (16) | 0.39844 (11) | 0.0640 (5) | |
H11 | 0.4517 | 0.2020 | 0.4285 | 0.077* | |
C12 | 0.39871 (18) | 0.08397 (17) | 0.34148 (12) | 0.0750 (6) | |
H12 | 0.4738 | 0.0485 | 0.3265 | 0.090* | |
C13 | 0.2832 (2) | 0.06328 (17) | 0.31323 (12) | 0.0763 (6) | |
H13 | 0.2644 | 0.0098 | 0.2742 | 0.092* | |
O1 | 0.07453 (11) | 0.28654 (13) | 0.43924 (8) | 0.0906 (5) | |
O2 | 0.19553 (11) | 0.13029 (11) | 0.34873 (8) | 0.0721 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0635 (11) | 0.0596 (12) | 0.0711 (13) | 0.0104 (10) | 0.0046 (10) | 0.0096 (11) |
C2 | 0.0856 (15) | 0.0541 (13) | 0.0842 (15) | 0.0070 (11) | 0.0162 (12) | 0.0047 (12) |
C3 | 0.0856 (15) | 0.0692 (15) | 0.0823 (15) | −0.0143 (13) | 0.0090 (13) | −0.0073 (12) |
C4 | 0.0623 (12) | 0.0841 (16) | 0.0862 (15) | −0.0053 (12) | 0.0036 (11) | −0.0043 (14) |
C5 | 0.0595 (11) | 0.0698 (13) | 0.0672 (13) | 0.0048 (10) | 0.0059 (10) | −0.0038 (11) |
C6 | 0.0574 (12) | 0.0557 (11) | 0.0521 (11) | 0.0045 (9) | 0.0043 (9) | 0.0075 (9) |
C7 | 0.0521 (10) | 0.0725 (13) | 0.0587 (11) | 0.0087 (10) | −0.0015 (9) | 0.0107 (10) |
C8 | 0.0495 (10) | 0.0718 (13) | 0.0593 (11) | 0.0085 (10) | 0.0013 (9) | 0.0029 (10) |
C9 | 0.0483 (10) | 0.0793 (14) | 0.0548 (11) | 0.0013 (10) | −0.0006 (9) | 0.0022 (11) |
C10 | 0.0513 (9) | 0.0655 (12) | 0.0488 (10) | −0.0033 (10) | 0.0013 (9) | −0.0005 (9) |
C11 | 0.0560 (11) | 0.0721 (14) | 0.0640 (12) | 0.0021 (10) | −0.0036 (10) | −0.0078 (11) |
C12 | 0.0626 (12) | 0.0818 (15) | 0.0804 (14) | 0.0101 (11) | 0.0000 (11) | −0.0139 (13) |
C13 | 0.0822 (14) | 0.0736 (14) | 0.0732 (14) | −0.0002 (12) | 0.0084 (12) | −0.0175 (11) |
O1 | 0.0492 (7) | 0.1257 (13) | 0.0971 (10) | 0.0116 (8) | −0.0048 (7) | −0.0287 (10) |
O2 | 0.0595 (7) | 0.0849 (9) | 0.0719 (9) | −0.0080 (7) | −0.0036 (7) | −0.0142 (8) |
Geometric parameters (Å, º) top
C1—C2 | 1.376 (2) | C7—H7 | 0.9300 |
C1—C6 | 1.389 (2) | C8—C9 | 1.471 (2) |
C1—H1 | 0.9300 | C8—H8 | 0.9300 |
C2—C3 | 1.371 (3) | C9—O1 | 1.2254 (18) |
C2—H2 | 0.9300 | C9—C10 | 1.448 (2) |
C3—C4 | 1.377 (3) | C10—C11 | 1.343 (2) |
C3—H3 | 0.9300 | C10—O2 | 1.3705 (19) |
C4—C5 | 1.374 (2) | C11—C12 | 1.400 (2) |
C4—H4 | 0.9300 | C11—H11 | 0.9300 |
C5—C6 | 1.389 (2) | C12—C13 | 1.320 (2) |
C5—H5 | 0.9300 | C12—H12 | 0.9300 |
C6—C7 | 1.458 (2) | C13—O2 | 1.357 (2) |
C7—C8 | 1.326 (2) | C13—H13 | 0.9300 |
| | | |
C2—C1—C6 | 121.46 (18) | C6—C7—H7 | 115.7 |
C2—C1—H1 | 119.3 | C7—C8—C9 | 122.49 (17) |
C6—C1—H1 | 119.3 | C7—C8—H8 | 118.8 |
C3—C2—C1 | 119.6 (2) | C9—C8—H8 | 118.8 |
C3—C2—H2 | 120.2 | O1—C9—C10 | 121.18 (18) |
C1—C2—H2 | 120.2 | O1—C9—C8 | 122.52 (18) |
C2—C3—C4 | 119.8 (2) | C10—C9—C8 | 116.30 (15) |
C2—C3—H3 | 120.1 | C11—C10—O2 | 109.07 (16) |
C4—C3—H3 | 120.1 | C11—C10—C9 | 133.63 (17) |
C5—C4—C3 | 120.82 (19) | O2—C10—C9 | 117.29 (15) |
C5—C4—H4 | 119.6 | C10—C11—C12 | 107.29 (17) |
C3—C4—H4 | 119.6 | C10—C11—H11 | 126.4 |
C4—C5—C6 | 120.15 (18) | C12—C11—H11 | 126.4 |
C4—C5—H5 | 119.9 | C13—C12—C11 | 106.64 (17) |
C6—C5—H5 | 119.9 | C13—C12—H12 | 126.7 |
C5—C6—C1 | 118.15 (18) | C11—C12—H12 | 126.7 |
C5—C6—C7 | 122.56 (17) | C12—C13—O2 | 111.06 (17) |
C1—C6—C7 | 119.29 (17) | C12—C13—H13 | 124.5 |
C8—C7—C6 | 128.54 (17) | O2—C13—H13 | 124.5 |
C8—C7—H7 | 115.7 | C13—O2—C10 | 105.95 (14) |
| | | |
C6—C1—C2—C3 | 0.6 (3) | C7—C8—C9—C10 | 169.79 (16) |
C1—C2—C3—C4 | 0.7 (3) | O1—C9—C10—C11 | −179.2 (2) |
C2—C3—C4—C5 | −1.3 (3) | C8—C9—C10—C11 | 1.3 (3) |
C3—C4—C5—C6 | 0.7 (3) | O1—C9—C10—O2 | 2.5 (3) |
C4—C5—C6—C1 | 0.5 (3) | C8—C9—C10—O2 | −177.05 (15) |
C4—C5—C6—C7 | −178.85 (16) | O2—C10—C11—C12 | 0.3 (2) |
C2—C1—C6—C5 | −1.2 (2) | C9—C10—C11—C12 | −178.19 (18) |
C2—C1—C6—C7 | 178.21 (16) | C10—C11—C12—C13 | 0.0 (2) |
C5—C6—C7—C8 | 2.0 (3) | C11—C12—C13—O2 | −0.3 (2) |
C1—C6—C7—C8 | −177.42 (17) | C12—C13—O2—C10 | 0.4 (2) |
C6—C7—C8—C9 | 178.54 (16) | C11—C10—O2—C13 | −0.41 (19) |
C7—C8—C9—O1 | −9.7 (3) | C9—C10—O2—C13 | 178.32 (15) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O1i | 0.93 | 2.48 | 3.347 (2) | 156 |
C11—H11···O1ii | 0.93 | 2.52 | 3.345 (2) | 149 |
C13—H13···Cg2iii | 0.93 | 2.58 | 3.410 (2) | 149 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x+1/2, −y+1/2, −z+1; (iii) x, −y−1/2, z−3/2. |