Ethyl 4-acetyl-5-oxo-3-phenyl-hexa-noate.

The reaction of ethyl 3-bromo-3-phenyl-propano-ate with pentane-2,4-dione, in the presence of palladium(II) acetate and triphenyl-phosphine, in dimethyl-formamide, unexpectedly gave the title product, C(16)H(20)O(4). The mol-ecule contains one chiral C atom but the crystal is racemic. In the crystal, neighboring mol-ecules form a chain along [100] through three weak C-H⋯O inter-actions. Furthermore, a double-stranded structure is formed through weak C-H⋯O inter-actions between two parallel chains.

Related literature

For Pd-catalysed coupling reactions, see: Hu et al. (2008 ▶); Hu, Ouyang et al. (2009 ▶); Hu, Yu et al. (2009 ▶). For the biological activity of pentane-2,4-dione derivatives, see: Vijaikumar & Pitchumani (2010 ▶). For related structures, see: Hu, Lin et al. (2010 ▶); Hu, Ren et al. (2010 ▶).

Experimental

Crystal data

C16H20O4

M = 276.32

Triclinic,

a = 5.8213 (11) Å

b = 7.7638 (18) Å

c = 17.8532 (15) Å

α = 80.973 (2)°

β = 88.977 (3)°

γ = 75.033 (2)°

V = 769.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 291 K

0.28 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.977, T max = 0.982

8564 measured reflections

3033 independent reflections

1726 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.099

S = 1.07

3033 reflections

185 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681100955X/bh2342sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100955X/bh2342Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H20O4	Z = 2
Mr = 276.32	F(000) = 296
Triclinic, P1	Dx = 1.192 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8213 (11) Å	Cell parameters from 3519 reflections
b = 7.7638 (18) Å	θ = 2.2–23.2°
c = 17.8532 (15) Å	µ = 0.09 mm−1
α = 80.973 (2)°	T = 291 K
β = 88.977 (3)°	Block, colourless
γ = 75.033 (2)°	0.28 × 0.24 × 0.22 mm
V = 769.6 (2) Å3

Bruker SMART APEX CCD diffractometer	3033 independent reflections
Radiation source: sealed tube	1726 reflections with I > 2σ(I)
graphite	Rint = 0.050
φ and ω scans	θmax = 26.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→7
Tmin = 0.977, Tmax = 0.982	k = −9→9
8564 measured reflections	l = −21→21

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)] = 0.050	H-atom parameters constrained
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.03P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3033 reflections	Δρmax = 0.16 e Å−3
185 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.017 (3)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
C1	0.9743 (3)	0.8135 (3)	0.22191 (11)	0.0424 (5)
C2	0.8295 (4)	0.7260 (3)	0.19182 (11)	0.0473 (5)
H2	0.7199	0.6823	0.2226	0.057*
C3	0.8438 (4)	0.7019 (3)	0.11675 (11)	0.0463 (5)
H3	0.7450	0.6411	0.0978	0.056*
C4	1.0006 (4)	0.7658 (3)	0.07023 (12)	0.0464 (5)
H4	1.0075	0.7507	0.0195	0.056*
C5	1.1474 (3)	0.8521 (3)	0.09850 (11)	0.0463 (5)
H5	1.2557	0.8957	0.0671	0.056*
C6	1.1361 (3)	0.8750 (3)	0.17330 (11)	0.0436 (5)
H6	1.2389	0.9329	0.1920	0.052*
C7	0.9534 (4)	0.8488 (3)	0.30314 (11)	0.0411 (5)
H7	0.8304	0.7949	0.3272	0.049*
C8	0.8736 (3)	1.0549 (3)	0.30396 (11)	0.0400 (5)
H8A	0.8589	1.0774	0.3560	0.048*
H8B	0.9929	1.1111	0.2802	0.048*
C9	0.6410 (3)	1.1362 (3)	0.26269 (11)	0.0411 (5)
C10	0.4381 (4)	1.3543 (3)	0.16176 (11)	0.0488 (5)
H10A	0.4133	1.4844	0.1540	0.059*
H10B	0.3032	1.3256	0.1887	0.059*
C11	0.4545 (4)	1.2916 (3)	0.08822 (11)	0.0470 (5)
H11A	0.5764	1.3323	0.0593	0.070*
H11B	0.3048	1.3394	0.0612	0.070*
H11C	0.4931	1.1621	0.0960	0.070*
C12	1.1855 (3)	0.7662 (3)	0.34946 (11)	0.0409 (5)
H12	1.3046	0.8279	0.3281	0.049*
C13	1.2830 (3)	0.5652 (3)	0.34769 (11)	0.0441 (5)
C14	1.1213 (4)	0.4433 (3)	0.36507 (12)	0.0490 (5)
H14A	1.2115	0.3200	0.3675	0.074*
H14B	1.0003	0.4717	0.3259	0.074*
H14C	1.0483	0.4599	0.4130	0.074*
C15	1.1577 (4)	0.7879 (3)	0.43302 (12)	0.0498 (5)
C16	1.3691 (4)	0.8014 (3)	0.47412 (12)	0.0471 (5)
H16A	1.3837	0.9232	0.4638	0.071*
H16B	1.5089	0.7214	0.4577	0.071*
H16C	1.3520	0.7683	0.5276	0.071*
O1	0.4638 (2)	1.0866 (2)	0.27737 (8)	0.0483 (4)
O2	0.6542 (2)	1.2691 (2)	0.20664 (8)	0.0509 (4)
O3	1.4918 (2)	0.50694 (19)	0.33553 (7)	0.0458 (4)
O4	0.9718 (2)	0.7909 (2)	0.46421 (8)	0.0488 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0433 (11)	0.0391 (11)	0.0406 (10)	−0.0055 (9)	−0.0051 (8)	−0.0021 (8)
C2	0.0545 (12)	0.0471 (13)	0.0438 (11)	−0.0141 (10)	−0.0010 (9)	−0.0156 (9)
C3	0.0473 (12)	0.0497 (12)	0.0450 (11)	−0.0135 (10)	−0.0033 (9)	−0.0146 (9)
C4	0.0454 (11)	0.0485 (12)	0.0480 (12)	−0.0147 (10)	−0.0068 (9)	−0.0103 (9)
C5	0.0433 (12)	0.0503 (13)	0.0472 (12)	−0.0173 (10)	0.0016 (9)	−0.0047 (9)
C6	0.0412 (11)	0.0426 (12)	0.0476 (12)	−0.0110 (9)	−0.0007 (9)	−0.0080 (9)
C7	0.0464 (11)	0.0380 (11)	0.0403 (11)	−0.0132 (9)	0.0007 (8)	−0.0061 (8)
C8	0.0374 (10)	0.0419 (11)	0.0428 (11)	−0.0108 (9)	0.0021 (8)	−0.0122 (9)
C9	0.0432 (12)	0.0350 (11)	0.0471 (11)	−0.0120 (9)	0.0015 (9)	−0.0095 (8)
C10	0.0559 (13)	0.0427 (12)	0.0440 (11)	−0.0128 (10)	−0.0086 (9)	0.0062 (9)
C11	0.0435 (11)	0.0469 (12)	0.0532 (12)	−0.0131 (9)	−0.0146 (9)	−0.0118 (10)
C12	0.0341 (10)	0.0470 (12)	0.0445 (11)	−0.0182 (9)	0.0047 (8)	−0.0034 (9)
C13	0.0344 (11)	0.0526 (12)	0.0452 (11)	−0.0115 (9)	0.0020 (8)	−0.0066 (9)
C14	0.0525 (13)	0.0453 (13)	0.0474 (12)	−0.0148 (10)	0.0069 (9)	0.0013 (10)
C15	0.0417 (12)	0.0572 (14)	0.0509 (12)	−0.0127 (10)	−0.0015 (10)	−0.0095 (10)
C16	0.0522 (12)	0.0447 (11)	0.0487 (11)	−0.0125 (10)	−0.0114 (9)	−0.0183 (9)
O1	0.0402 (8)	0.0558 (9)	0.0467 (8)	−0.0135 (7)	−0.0032 (6)	0.0010 (7)
O2	0.0538 (9)	0.0545 (9)	0.0414 (8)	−0.0152 (7)	−0.0036 (6)	0.0040 (7)
O3	0.0435 (8)	0.0476 (9)	0.0474 (8)	−0.0082 (6)	0.0065 (6)	−0.0177 (6)
O4	0.0493 (9)	0.0499 (9)	0.0495 (8)	−0.0138 (7)	0.0131 (7)	−0.0142 (7)

C1—C2	1.374 (3)	C10—O2	1.450 (2)
C1—C6	1.393 (3)	C10—C11	1.464 (3)
C1—C7	1.515 (3)	C10—H10A	0.9700
C2—C3	1.380 (3)	C10—H10B	0.9700
C2—H2	0.9300	C11—H11A	0.9600
C3—C4	1.359 (3)	C11—H11B	0.9600
C3—H3	0.9300	C11—H11C	0.9600
C4—C5	1.360 (3)	C12—C13	1.522 (3)
C4—H4	0.9300	C12—C15	1.528 (3)
C5—C6	1.373 (3)	C12—H12	0.9800
C5—H5	0.9300	C13—O3	1.211 (2)
C6—H6	0.9300	C13—C14	1.495 (3)
C7—C12	1.532 (3)	C14—H14A	0.9600
C7—C8	1.549 (3)	C14—H14B	0.9600
C7—H7	0.9800	C14—H14C	0.9600
C8—C9	1.491 (3)	C15—O4	1.205 (2)
C8—H8A	0.9700	C15—C16	1.479 (3)
C8—H8B	0.9700	C16—H16A	0.9600
C9—O1	1.202 (2)	C16—H16B	0.9600
C9—O2	1.337 (2)	C16—H16C	0.9600
C2—C1—C6	116.86 (19)	C11—C10—H10A	109.6
C2—C1—C7	121.89 (19)	O2—C10—H10B	109.6
C6—C1—C7	121.21 (19)	C11—C10—H10B	109.6
C1—C2—C3	121.2 (2)	H10A—C10—H10B	108.1
C1—C2—H2	119.4	C10—C11—H11A	109.5
C3—C2—H2	119.4	C10—C11—H11B	109.5
C4—C3—C2	120.8 (2)	H11A—C11—H11B	109.5
C4—C3—H3	119.6	C10—C11—H11C	109.5
C2—C3—H3	119.6	H11A—C11—H11C	109.5
C3—C4—C5	119.4 (2)	H11B—C11—H11C	109.5
C3—C4—H4	120.3	C13—C12—C15	106.57 (16)
C5—C4—H4	120.3	C13—C12—C7	113.03 (16)
C4—C5—C6	120.2 (2)	C15—C12—C7	112.55 (16)
C4—C5—H5	119.9	C13—C12—H12	108.2
C6—C5—H5	119.9	C15—C12—H12	108.2
C5—C6—C1	121.58 (19)	C7—C12—H12	108.2
C5—C6—H6	119.2	O3—C13—C14	121.6 (2)
C1—C6—H6	119.2	O3—C13—C12	119.19 (18)
C1—C7—C12	112.74 (16)	C14—C13—C12	119.09 (17)
C1—C7—C8	109.58 (15)	C13—C14—H14A	109.5
C12—C7—C8	109.89 (15)	C13—C14—H14B	109.5
C1—C7—H7	108.2	H14A—C14—H14B	109.5
C12—C7—H7	108.2	C13—C14—H14C	109.5
C8—C7—H7	108.2	H14A—C14—H14C	109.5
C9—C8—C7	110.65 (15)	H14B—C14—H14C	109.5
C9—C8—H8A	109.5	O4—C15—C16	121.6 (2)
C7—C8—H8A	109.5	O4—C15—C12	121.10 (18)
C9—C8—H8B	109.5	C16—C15—C12	117.33 (19)
C7—C8—H8B	109.5	C15—C16—H16A	109.5
H8A—C8—H8B	108.1	C15—C16—H16B	109.5
O1—C9—O2	124.06 (18)	H16A—C16—H16B	109.5
O1—C9—C8	124.11 (18)	C15—C16—H16C	109.5
O2—C9—C8	111.82 (16)	H16A—C16—H16C	109.5
O2—C10—C11	110.33 (17)	H16B—C16—H16C	109.5
O2—C10—H10A	109.6	C9—O2—C10	116.13 (15)
C6—C1—C2—C3	−0.4 (3)	C1—C7—C12—C13	−54.2 (2)
C7—C1—C2—C3	177.12 (18)	C8—C7—C12—C13	−176.77 (16)
C1—C2—C3—C4	−0.7 (3)	C1—C7—C12—C15	−175.02 (18)
C2—C3—C4—C5	1.0 (3)	C8—C7—C12—C15	62.4 (2)
C3—C4—C5—C6	−0.3 (3)	C15—C12—C13—O3	−102.9 (2)
C4—C5—C6—C1	−0.8 (3)	C7—C12—C13—O3	132.96 (18)
C2—C1—C6—C5	1.1 (3)	C15—C12—C13—C14	73.9 (2)
C7—C1—C6—C5	−176.43 (18)	C7—C12—C13—C14	−50.2 (2)
C2—C1—C7—C12	122.1 (2)	C13—C12—C15—O4	−93.4 (2)
C6—C1—C7—C12	−60.5 (2)	C7—C12—C15—O4	31.0 (3)
C2—C1—C7—C8	−115.2 (2)	C13—C12—C15—C16	85.4 (2)
C6—C1—C7—C8	62.2 (2)	C7—C12—C15—C16	−150.14 (18)
C1—C7—C8—C9	58.7 (2)	O1—C9—O2—C10	−0.5 (3)
C12—C7—C8—C9	−176.91 (16)	C8—C9—O2—C10	178.60 (17)
C7—C8—C9—O1	55.4 (3)	C11—C10—O2—C9	−103.9 (2)
C7—C8—C9—O2	−123.67 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.93	2.63	3.534 (2)	165
C8—H8B···O1i	0.97	2.70	3.525 (2)	144
C12—H12···O1i	0.98	2.46	3.387 (2)	157
C14—H14C···O4ii	0.96	2.72	3.405 (2)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.93	2.63	3.534 (2)	165
C8—H8B⋯O1i	0.97	2.70	3.525 (2)	144
C12—H12⋯O1i	0.98	2.46	3.387 (2)	157
C14—H14C⋯O4ii	0.96	2.72	3.405 (2)	129

Symmetry codes: (i) ; (ii) .