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In the title mol­ecule, C18H16O3, the configuaration with respect to the C=C double bond is E. The benzoyl group is rotated out of the mean plane through the rest of the mol­ecule by 88.31 (4)°. In the crystal structure, mol­ecules are linked by weak inter­molecular C—H...O inter­actions to form two-dimensional sheets.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806001863/lh6578sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806001863/lh6578Isup2.hkl
Contains datablock I

CCDC reference: 298495

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.035
  • wR factor = 0.102
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: WinGX (Version 1.64.05; Farrugia, 1999); software used to prepare material for publication: SHELXL97.

Ethyl (E)-2-benzoyl-3-phenylpropenoate top
Crystal data top
C18H16O3F(000) = 592
Mr = 280.31Dx = 1.281 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8602 reflections
a = 10.8099 (8) Åθ = 2.3–27.9°
b = 7.2746 (5) ŵ = 0.09 mm1
c = 18.5285 (13) ÅT = 273 K
β = 94.326 (1)°Block, colourless
V = 1452.89 (18) Å30.18 × 0.11 × 0.09 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2297 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 25.0°, θmin = 2.1°
ω scansh = 1212
13392 measured reflectionsk = 88
2557 independent reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0596P)2 + 0.2059P]
where P = (Fo2 + 2Fc2)/3
2557 reflections(Δ/σ)max < 0.001
191 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.16 e Å3
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
O610.79812 (10)0.60748 (13)0.10177 (5)0.0644 (3)
O111.02055 (9)0.37277 (17)0.19795 (5)0.0699 (3)
O120.92331 (8)0.34751 (13)0.29982 (4)0.0520 (3)
C30.69893 (11)0.34225 (16)0.22411 (6)0.0430 (3)
H30.71290.31210.27280.052*
C60.80669 (10)0.44350 (17)0.11334 (6)0.0430 (3)
C20.80163 (11)0.37632 (16)0.19014 (6)0.0418 (3)
C10.92660 (11)0.36443 (17)0.22863 (6)0.0451 (3)
C41.04081 (11)0.33726 (19)0.34245 (7)0.0518 (3)
H4A1.09100.44460.33400.062*
H4B1.08620.22830.32980.062*
C51.01122 (14)0.3293 (2)0.41983 (7)0.0617 (4)
H5A0.97020.44070.43220.092*
H5B1.08660.31560.45020.092*
H5C0.95780.22630.42680.092*
C70.82624 (10)0.30985 (16)0.05464 (6)0.0405 (3)
C80.85605 (11)0.37595 (18)0.01212 (6)0.0477 (3)
H80.86450.50180.01900.057*
C90.87316 (12)0.2569 (2)0.06816 (7)0.0574 (3)
H90.89370.30230.11260.069*
C100.85983 (13)0.0705 (2)0.05842 (7)0.0603 (4)
H100.87120.00990.09640.072*
C110.82952 (13)0.00238 (19)0.00763 (7)0.0569 (3)
H110.81980.12350.01390.068*
C120.81370 (11)0.12141 (17)0.06419 (7)0.0480 (3)
H120.79460.07540.10880.058*
C130.56841 (11)0.34491 (16)0.19689 (6)0.0432 (3)
C140.52486 (12)0.34189 (18)0.12406 (7)0.0495 (3)
H140.58140.33930.08860.059*
C150.39981 (12)0.34267 (19)0.10380 (8)0.0559 (3)
H150.37280.34050.05490.067*
C160.31416 (12)0.34666 (19)0.15517 (8)0.0582 (4)
H160.22970.34770.14120.070*
C170.35481 (13)0.3491 (2)0.22726 (8)0.0661 (4)
H170.29760.35200.26230.079*
C180.47995 (12)0.3471 (2)0.24783 (7)0.0577 (4)
H180.50600.34720.29680.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O610.0935 (8)0.0500 (6)0.0517 (6)0.0035 (5)0.0196 (5)0.0062 (4)
O110.0417 (5)0.1186 (9)0.0507 (6)0.0030 (5)0.0110 (4)0.0034 (5)
O120.0412 (5)0.0765 (6)0.0381 (5)0.0024 (4)0.0013 (4)0.0030 (4)
C30.0450 (7)0.0506 (7)0.0338 (6)0.0005 (5)0.0049 (5)0.0030 (5)
C60.0395 (6)0.0508 (7)0.0392 (6)0.0016 (5)0.0061 (5)0.0054 (5)
C20.0431 (6)0.0470 (6)0.0356 (6)0.0010 (5)0.0051 (5)0.0002 (5)
C10.0436 (7)0.0532 (7)0.0389 (6)0.0026 (5)0.0061 (5)0.0008 (5)
C40.0424 (7)0.0632 (8)0.0487 (7)0.0001 (5)0.0038 (5)0.0005 (6)
C50.0607 (8)0.0779 (10)0.0448 (7)0.0004 (7)0.0061 (6)0.0044 (6)
C70.0326 (5)0.0532 (7)0.0357 (6)0.0002 (5)0.0029 (4)0.0036 (5)
C80.0458 (7)0.0572 (7)0.0408 (6)0.0017 (5)0.0074 (5)0.0048 (5)
C90.0574 (8)0.0772 (9)0.0389 (6)0.0006 (7)0.0126 (5)0.0006 (6)
C100.0588 (8)0.0724 (9)0.0499 (7)0.0052 (7)0.0060 (6)0.0137 (7)
C110.0582 (8)0.0522 (7)0.0599 (8)0.0017 (6)0.0013 (6)0.0025 (6)
C120.0468 (7)0.0551 (7)0.0420 (6)0.0005 (5)0.0030 (5)0.0066 (5)
C130.0422 (6)0.0470 (7)0.0410 (6)0.0007 (5)0.0072 (5)0.0046 (5)
C140.0430 (7)0.0637 (8)0.0427 (7)0.0001 (5)0.0081 (5)0.0010 (6)
C150.0472 (7)0.0702 (9)0.0497 (7)0.0005 (6)0.0005 (6)0.0015 (6)
C160.0395 (7)0.0671 (9)0.0683 (9)0.0005 (6)0.0053 (6)0.0068 (7)
C170.0466 (8)0.0932 (12)0.0606 (9)0.0005 (7)0.0188 (6)0.0124 (7)
C180.0481 (7)0.0825 (10)0.0437 (7)0.0020 (6)0.0111 (6)0.0113 (6)
Geometric parameters (Å, º) top
O61—C61.2143 (15)C8—H80.9300
O11—C11.2022 (15)C9—C101.377 (2)
O12—C11.3279 (14)C9—H90.9300
O12—C41.4462 (15)C10—C111.3825 (19)
C3—C21.3398 (16)C10—H100.9300
C3—C131.4622 (17)C11—C121.3800 (18)
C3—H30.9300C11—H110.9300
C6—C71.4857 (17)C12—H120.9300
C6—C21.5095 (15)C13—C181.3935 (17)
C2—C11.4818 (17)C13—C141.3953 (18)
C4—C51.4935 (19)C14—C151.3754 (18)
C4—H4A0.9700C14—H140.9300
C4—H4B0.9700C15—C161.3774 (19)
C5—H5A0.9600C15—H150.9300
C5—H5B0.9600C16—C171.374 (2)
C5—H5C0.9600C16—H160.9300
C7—C81.3875 (16)C17—C181.378 (2)
C7—C121.3902 (17)C17—H170.9300
C8—C91.3752 (19)C18—H180.9300
C1—O12—C4117.33 (9)C8—C9—C10119.99 (12)
C2—C3—C13130.36 (11)C8—C9—H9120.0
C2—C3—H3114.8C10—C9—H9120.0
C13—C3—H3114.8C9—C10—C11120.19 (12)
O61—C6—C7121.79 (10)C9—C10—H10119.9
O61—C6—C2118.47 (11)C11—C10—H10119.9
C7—C6—C2119.70 (10)C12—C11—C10119.92 (13)
C3—C2—C1121.38 (10)C12—C11—H11120.0
C3—C2—C6126.36 (11)C10—C11—H11120.0
C1—C2—C6112.09 (9)C11—C12—C7120.21 (12)
O11—C1—O12124.14 (11)C11—C12—H12119.9
O11—C1—C2122.78 (11)C7—C12—H12119.9
O12—C1—C2113.06 (10)C18—C13—C14117.16 (12)
O12—C4—C5106.47 (10)C18—C13—C3117.39 (11)
O12—C4—H4A110.4C14—C13—C3125.43 (11)
C5—C4—H4A110.4C15—C14—C13121.12 (12)
O12—C4—H4B110.4C15—C14—H14119.4
C5—C4—H4B110.4C13—C14—H14119.4
H4A—C4—H4B108.6C14—C15—C16120.63 (13)
C4—C5—H5A109.5C14—C15—H15119.7
C4—C5—H5B109.5C16—C15—H15119.7
H5A—C5—H5B109.5C17—C16—C15119.31 (13)
C4—C5—H5C109.5C17—C16—H16120.3
H5A—C5—H5C109.5C15—C16—H16120.3
H5B—C5—H5C109.5C16—C17—C18120.27 (13)
C8—C7—C12119.12 (11)C16—C17—H17119.9
C8—C7—C6118.77 (11)C18—C17—H17119.9
C12—C7—C6122.10 (10)C17—C18—C13121.49 (13)
C9—C8—C7120.56 (13)C17—C18—H18119.3
C9—C8—H8119.7C13—C18—H18119.3
C7—C8—H8119.7
C13—C3—C2—C1179.61 (11)C6—C7—C8—C9179.07 (11)
C13—C3—C2—C65.5 (2)C7—C8—C9—C100.47 (19)
O61—C6—C2—C384.09 (16)C8—C9—C10—C110.1 (2)
C7—C6—C2—C398.03 (14)C9—C10—C11—C120.6 (2)
O61—C6—C2—C191.25 (13)C10—C11—C12—C71.00 (19)
C7—C6—C2—C186.64 (13)C8—C7—C12—C110.66 (18)
C4—O12—C1—O110.48 (19)C6—C7—C12—C11178.30 (11)
C4—O12—C1—C2179.20 (10)C2—C3—C13—C18164.95 (13)
C3—C2—C1—O11170.97 (13)C2—C3—C13—C1416.4 (2)
C6—C2—C1—O1113.43 (17)C18—C13—C14—C150.56 (19)
C3—C2—C1—O1210.28 (16)C3—C13—C14—C15179.25 (12)
C6—C2—C1—O12165.32 (10)C13—C14—C15—C160.1 (2)
C1—O12—C4—C5177.00 (11)C14—C15—C16—C170.3 (2)
O61—C6—C7—C810.94 (17)C15—C16—C17—C180.1 (2)
C2—C6—C7—C8166.88 (10)C16—C17—C18—C130.8 (2)
O61—C6—C7—C12168.02 (12)C14—C13—C18—C171.0 (2)
C2—C6—C7—C1214.16 (16)C3—C13—C18—C17179.79 (13)
C12—C7—C8—C90.08 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···O61i0.932.573.3911 (17)148
C16—H16···O11ii0.932.573.3343 (16)140
Symmetry codes: (i) x, y1, z; (ii) x1, y, z.
 

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