Ethyl (E)-2-benzoyl-3-phenyl­propenoate

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.

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

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Computing details

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

Crystal data

C18H16O3	F(000) = 592
Mr = 280.31	Dx = 1.281 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8602 reflections
a = 10.8099 (8) Å	θ = 2.3–27.9°
b = 7.2746 (5) Å	µ = 0.09 mm^−1
c = 18.5285 (13) Å	T = 273 K
β = 94.326 (1)°	Block, colourless
V = 1452.89 (18) Å^3	0.18 × 0.11 × 0.09 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2297 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 25.0°, θmin = 2.1°
ω scans	h = −12→12
13392 measured reflections	k = −8→8
2557 independent reflections	l = −22→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0596P)^2 + 0.2059P] where P = (Fo^2 + 2Fc^2)/3
2557 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O61	0.79812 (10)	0.60748 (13)	0.10177 (5)	0.0644 (3)
O11	1.02055 (9)	0.37277 (17)	0.19795 (5)	0.0699 (3)
O12	0.92331 (8)	0.34751 (13)	0.29982 (4)	0.0520 (3)
C3	0.69893 (11)	0.34225 (16)	0.22411 (6)	0.0430 (3)
H3	0.7129	0.3121	0.2728	0.052*
C6	0.80669 (10)	0.44350 (17)	0.11334 (6)	0.0430 (3)
C2	0.80163 (11)	0.37632 (16)	0.19014 (6)	0.0418 (3)
C1	0.92660 (11)	0.36443 (17)	0.22863 (6)	0.0451 (3)
C4	1.04081 (11)	0.33726 (19)	0.34245 (7)	0.0518 (3)
H4A	1.0910	0.4446	0.3340	0.062*
H4B	1.0862	0.2283	0.3298	0.062*
C5	1.01122 (14)	0.3293 (2)	0.41983 (7)	0.0617 (4)
H5A	0.9702	0.4407	0.4322	0.092*
H5B	1.0866	0.3156	0.4502	0.092*
H5C	0.9578	0.2263	0.4268	0.092*
C7	0.82624 (10)	0.30985 (16)	0.05464 (6)	0.0405 (3)
C8	0.85605 (11)	0.37595 (18)	−0.01212 (6)	0.0477 (3)
H8	0.8645	0.5018	−0.0190	0.057*
C9	0.87316 (12)	0.2569 (2)	−0.06816 (7)	0.0574 (3)
H9	0.8937	0.3023	−0.1126	0.069*
C10	0.85983 (13)	0.0705 (2)	−0.05842 (7)	0.0603 (4)
H10	0.8712	−0.0099	−0.0964	0.072*
C11	0.82952 (13)	0.00238 (19)	0.00763 (7)	0.0569 (3)
H11	0.8198	−0.1235	0.0139	0.068*
C12	0.81370 (11)	0.12141 (17)	0.06419 (7)	0.0480 (3)
H12	0.7946	0.0754	0.1088	0.058*
C13	0.56841 (11)	0.34491 (16)	0.19689 (6)	0.0432 (3)
C14	0.52486 (12)	0.34189 (18)	0.12406 (7)	0.0495 (3)
H14	0.5814	0.3393	0.0886	0.059*
C15	0.39981 (12)	0.34267 (19)	0.10380 (8)	0.0559 (3)
H15	0.3728	0.3405	0.0549	0.067*
C16	0.31416 (12)	0.34666 (19)	0.15517 (8)	0.0582 (4)
H16	0.2297	0.3477	0.1412	0.070*
C17	0.35481 (13)	0.3491 (2)	0.22726 (8)	0.0661 (4)
H17	0.2976	0.3520	0.2623	0.079*
C18	0.47995 (12)	0.3471 (2)	0.24783 (7)	0.0577 (4)
H18	0.5060	0.3472	0.2968	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O61	0.0935 (8)	0.0500 (6)	0.0517 (6)	0.0035 (5)	0.0196 (5)	0.0062 (4)
O11	0.0417 (5)	0.1186 (9)	0.0507 (6)	−0.0030 (5)	0.0110 (4)	0.0034 (5)
O12	0.0412 (5)	0.0765 (6)	0.0381 (5)	−0.0024 (4)	0.0013 (4)	0.0030 (4)
C3	0.0450 (7)	0.0506 (7)	0.0338 (6)	−0.0005 (5)	0.0049 (5)	0.0030 (5)
C6	0.0395 (6)	0.0508 (7)	0.0392 (6)	−0.0016 (5)	0.0061 (5)	0.0054 (5)
C2	0.0431 (6)	0.0470 (6)	0.0356 (6)	−0.0010 (5)	0.0051 (5)	−0.0002 (5)
C1	0.0436 (7)	0.0532 (7)	0.0389 (6)	−0.0026 (5)	0.0061 (5)	0.0008 (5)
C4	0.0424 (7)	0.0632 (8)	0.0487 (7)	−0.0001 (5)	−0.0038 (5)	−0.0005 (6)
C5	0.0607 (8)	0.0779 (10)	0.0448 (7)	0.0004 (7)	−0.0061 (6)	−0.0044 (6)
C7	0.0326 (5)	0.0532 (7)	0.0357 (6)	0.0002 (5)	0.0029 (4)	0.0036 (5)
C8	0.0458 (7)	0.0572 (7)	0.0408 (6)	−0.0017 (5)	0.0074 (5)	0.0048 (5)
C9	0.0574 (8)	0.0772 (9)	0.0389 (6)	−0.0006 (7)	0.0126 (5)	0.0006 (6)
C10	0.0588 (8)	0.0724 (9)	0.0499 (7)	0.0052 (7)	0.0060 (6)	−0.0137 (7)
C11	0.0582 (8)	0.0522 (7)	0.0599 (8)	0.0017 (6)	0.0013 (6)	−0.0025 (6)
C12	0.0468 (7)	0.0551 (7)	0.0420 (6)	0.0005 (5)	0.0030 (5)	0.0066 (5)
C13	0.0422 (6)	0.0470 (7)	0.0410 (6)	−0.0007 (5)	0.0072 (5)	0.0046 (5)
C14	0.0430 (7)	0.0637 (8)	0.0427 (7)	0.0001 (5)	0.0081 (5)	−0.0010 (6)
C15	0.0472 (7)	0.0702 (9)	0.0497 (7)	0.0005 (6)	−0.0005 (6)	−0.0015 (6)
C16	0.0395 (7)	0.0671 (9)	0.0683 (9)	−0.0005 (6)	0.0053 (6)	0.0068 (7)
C17	0.0466 (8)	0.0932 (12)	0.0606 (9)	0.0005 (7)	0.0188 (6)	0.0124 (7)
C18	0.0481 (7)	0.0825 (10)	0.0437 (7)	−0.0020 (6)	0.0111 (6)	0.0113 (6)

Geometric parameters (Å, º)

O61—C6	1.2143 (15)	C8—H8	0.9300
O11—C1	1.2022 (15)	C9—C10	1.377 (2)
O12—C1	1.3279 (14)	C9—H9	0.9300
O12—C4	1.4462 (15)	C10—C11	1.3825 (19)
C3—C2	1.3398 (16)	C10—H10	0.9300
C3—C13	1.4622 (17)	C11—C12	1.3800 (18)
C3—H3	0.9300	C11—H11	0.9300
C6—C7	1.4857 (17)	C12—H12	0.9300
C6—C2	1.5095 (15)	C13—C18	1.3935 (17)
C2—C1	1.4818 (17)	C13—C14	1.3953 (18)
C4—C5	1.4935 (19)	C14—C15	1.3754 (18)
C4—H4A	0.9700	C14—H14	0.9300
C4—H4B	0.9700	C15—C16	1.3774 (19)
C5—H5A	0.9600	C15—H15	0.9300
C5—H5B	0.9600	C16—C17	1.374 (2)
C5—H5C	0.9600	C16—H16	0.9300
C7—C8	1.3875 (16)	C17—C18	1.378 (2)
C7—C12	1.3902 (17)	C17—H17	0.9300
C8—C9	1.3752 (19)	C18—H18	0.9300
C1—O12—C4	117.33 (9)	C8—C9—C10	119.99 (12)
C2—C3—C13	130.36 (11)	C8—C9—H9	120.0
C2—C3—H3	114.8	C10—C9—H9	120.0
C13—C3—H3	114.8	C9—C10—C11	120.19 (12)
O61—C6—C7	121.79 (10)	C9—C10—H10	119.9
O61—C6—C2	118.47 (11)	C11—C10—H10	119.9
C7—C6—C2	119.70 (10)	C12—C11—C10	119.92 (13)
C3—C2—C1	121.38 (10)	C12—C11—H11	120.0
C3—C2—C6	126.36 (11)	C10—C11—H11	120.0
C1—C2—C6	112.09 (9)	C11—C12—C7	120.21 (12)
O11—C1—O12	124.14 (11)	C11—C12—H12	119.9
O11—C1—C2	122.78 (11)	C7—C12—H12	119.9
O12—C1—C2	113.06 (10)	C18—C13—C14	117.16 (12)
O12—C4—C5	106.47 (10)	C18—C13—C3	117.39 (11)
O12—C4—H4A	110.4	C14—C13—C3	125.43 (11)
C5—C4—H4A	110.4	C15—C14—C13	121.12 (12)
O12—C4—H4B	110.4	C15—C14—H14	119.4
C5—C4—H4B	110.4	C13—C14—H14	119.4
H4A—C4—H4B	108.6	C14—C15—C16	120.63 (13)
C4—C5—H5A	109.5	C14—C15—H15	119.7
C4—C5—H5B	109.5	C16—C15—H15	119.7
H5A—C5—H5B	109.5	C17—C16—C15	119.31 (13)
C4—C5—H5C	109.5	C17—C16—H16	120.3
H5A—C5—H5C	109.5	C15—C16—H16	120.3
H5B—C5—H5C	109.5	C16—C17—C18	120.27 (13)
C8—C7—C12	119.12 (11)	C16—C17—H17	119.9
C8—C7—C6	118.77 (11)	C18—C17—H17	119.9
C12—C7—C6	122.10 (10)	C17—C18—C13	121.49 (13)
C9—C8—C7	120.56 (13)	C17—C18—H18	119.3
C9—C8—H8	119.7	C13—C18—H18	119.3
C7—C8—H8	119.7
C13—C3—C2—C1	−179.61 (11)	C6—C7—C8—C9	−179.07 (11)
C13—C3—C2—C6	5.5 (2)	C7—C8—C9—C10	0.47 (19)
O61—C6—C2—C3	84.09 (16)	C8—C9—C10—C11	−0.1 (2)
C7—C6—C2—C3	−98.03 (14)	C9—C10—C11—C12	−0.6 (2)
O61—C6—C2—C1	−91.25 (13)	C10—C11—C12—C7	1.00 (19)
C7—C6—C2—C1	86.64 (13)	C8—C7—C12—C11	−0.66 (18)
C4—O12—C1—O11	−0.48 (19)	C6—C7—C12—C11	178.30 (11)
C4—O12—C1—C2	−179.20 (10)	C2—C3—C13—C18	−164.95 (13)
C3—C2—C1—O11	170.97 (13)	C2—C3—C13—C14	16.4 (2)
C6—C2—C1—O11	−13.43 (17)	C18—C13—C14—C15	0.56 (19)
C3—C2—C1—O12	−10.28 (16)	C3—C13—C14—C15	179.25 (12)
C6—C2—C1—O12	165.32 (10)	C13—C14—C15—C16	0.1 (2)
C1—O12—C4—C5	177.00 (11)	C14—C15—C16—C17	−0.3 (2)
O61—C6—C7—C8	10.94 (17)	C15—C16—C17—C18	−0.1 (2)
C2—C6—C7—C8	−166.88 (10)	C16—C17—C18—C13	0.8 (2)
O61—C6—C7—C12	−168.02 (12)	C14—C13—C18—C17	−1.0 (2)
C2—C6—C7—C12	14.16 (16)	C3—C13—C18—C17	−179.79 (13)
C12—C7—C8—C9	−0.08 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O61^i	0.93	2.57	3.3911 (17)	148
C16—H16···O11^ii	0.93	2.57	3.3343 (16)	140

Symmetry codes: (i) x, y−1, z; (ii) x−1, y, z.