1,4 Di­acetyl­benzene

organic papers

o1582

10H10O2 doi:10.1107/S1600536806010440 Acta Cryst.(2006). E62, o1582–o1583

Acta Crystallographica Section E Structure Reports

Online

ISSN 1600-5368

1,4-Diacetylbenzene

Shan Liu,aZhen-Yi Wu,aNing

Shan,bDan-Dan Wangaand

Hong-Jun Zhua*

a_{Department of Applied Chemistry, College of}

Science, Nanjing University of Technology, Nanjing 210009, People’s Republic of China, andb_{Institute of Chemical and Engineering}

Sciences, The Singapore Government Agency for Science, Technology and Research, 627833, Singapore

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study

T= 180 K

Mean(C–C) = 0.002 A˚

Rfactor = 0.069

wRfactor = 0.195

Data-to-parameter ratio = 20.7

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

Received 6 March 2006 Accepted 22 March 2006

#2006 International Union of Crystallography

All rights reserved

The asymmetric unit of the title compound, C10H10O2,

contains two half-molecules, each molecules being located on a centre of inversion. The dihedral angle between the planes of the two independent molecules is 39.67 (4)_.

Comment

1,4-Diacetylbenzene is used in polymerization reactions to obtain polymers of quinoline derivatives (Bracke, 1969; Imai

et al., 1975). We report here the crystal structure of the title compound, (I).

The asymmetric unit of (I) contains two half-molecules, each molecule being located on a centre of inversion (Fig. 1). Selected geometric parameters are listed in Table 1. Corres-ponding bond lengths and angles in the two independent molecules agree with each other. Both the molecules are essentially planar; the dihedral angle between the planes of the two molecules is 39.67 (4)_{. No–stacking interactions}

or hydrogen bonds are observed in the crystal structure (Fig. 2).

Experimental

p-Ethylacetophenone (14.825 g, 0.1 mol) was added dropwise to a mixture of magnesium oxide (10.0 g, 0.25 mol), water (258 ml), concentrated nitric acid (34 ml, 0.53 mol) and potassium permanga-nate (39.5 g, 0.25 mol), with stirring at 332–334 K. The mixture was stirred further at 331–335 K for 4.5 h and then cooled, filtered by vacuum and dried. The powdered residue was dissolved in hot benzene (300 ml) to extract the crude product. This was slurried with cold anhydrous diethyl ether (70 ml), filtered, and dried to obtain white crystals of the title compound (13.3 g). Single crystals suitable for X-ray diffraction were obtained by dissolving the compound (2.0 g, 12.3 mmol) in benzene (25 ml) and allowing the solution to evaporate at room temperature for about 15 d.

Crystal data

C10H10O2

Mr= 162.18

Monoclinic,P2₁=n a= 12.699 (3) A˚

b= 5.4604 (11) A˚

c= 12.950 (3) A˚

= 114.07 (3) V= 819.9 (4) A˚3

Z= 4

Dx= 1.314 Mg m

3 MoKradiation Cell parameters from 2627

reflections

= 1.7–31.1

= 0.09 mm1

Data collection

Bruker SMART CCD area-detector diffractometer

’and!scans

Absorption correction: multi-scan (SADABS; Sheldrick, 2002)

Tmin= 0.979,Tmax= 0.992 6624 measured reflections

2297 independent reflections 1979 reflections withI> 2(I)

Rint= 0.024

max= 31.3

h=18!18

k=7!6

l=16!17

Refinement

Refinement onF2

R[F2_{> 2(F}2_{)] = 0.069}

wR(F2_{) = 0.195}

S= 1.16 2297 reflections 111 parameters

H-atom parameters constrained

w= 1/[2_(F

o2) + (0.0962P)2 + 0.1961P]

whereP= (Fo2+ 2Fc2)/3 (/)max= 0.001

max= 0.29 e A˚

3

min=0.27 e A˚

3

Table 1

Selected geometric parameters (A˚ ,_).

O1—C4 1.221 (2) O2—C9 1.218 (2)

O1—C4—C1 119.89 (15) O1—C4—C5 121.29 (14)

O2—C9—C10 121.12 (15) O2—C9—C6 120.23 (15)

H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.95 (aromatic) or 0.97(methyl) A˚ , and withUiso(H) = 1.2 or 1.5(methyl) timesUeq(C).

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:

SHELXTL (Bruker, 2001); software used to prepare material for publication:SHELXTL.

References

Bracke, W. (1969).Macromolecules,2, 286–289.

Bruker (2001).SMART,SAINTandSHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.

Imai, Y., Johnson, E. F., Katto, T., Katto, T., Kurihara, M. & Stille, J. K. (1975).

J. Polym. Sci.13, 2233–2249.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.

Sheldrick, G. M. (2002).SADABS. University of Go¨ttingen, Germany.

Figure 1

The asymmetric unit of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Atoms labeled with the suffixes A and B are generated by the symmetry operations (1x,y,z) and (2x,y,z), respectively.

Figure 2

supporting information

sup-1 Acta Cryst. (2006). E62, o1582–o1583

supporting information

Acta Cryst. (2006). E62, o1582–o1583 [https://doi.org/10.1107/S1600536806010440]

1,4-Diacetylbenzene

Shan Liu, Zhen-Yi Wu, Ning Shan, Dan-Dan Wang and Hong-Jun Zhu

1,4-Diacetylbenzene

Crystal data

C10H10O2 Mr = 162.18 Monoclinic, P21/n

Hall symbol: -P 2yn

a = 12.699 (3) Å

b = 5.4604 (11) Å

c = 12.950 (3) Å

β = 114.07 (3)°

V = 819.9 (4) Å3 Z = 4

F(000) = 344

Dx = 1.314 Mg m−3 Dm = 1.314 Mg m−3

Dm measured by not measured

Melting point: 113(1) K Mo Kα radiation, λ = 0.71073 Å Cell parameters from 2627 reflections

θ = 1.7–31.1°

µ = 0.09 mm−1 T = 180 K Prism, colourless 0.24 × 0.15 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

Detector resolution: 28.5714 pixels mm-1 φ and ω scans

Absorption correction: multi-scan (SADABS; Sheldrick, 2002)

Tmin = 0.979, Tmax = 0.992

6624 measured reflections 2297 independent reflections 1979 reflections with I > 2σ(I)

Rint = 0.024

θmax = 31.3°, θmin = 1.9° h = −18→18

k = −7→6

l = −16→17

Refinement

Refinement on F2

Least-squares matrix: full

R[F2 _{> 2σ(F}2_{)] = 0.069} wR(F2_{) = 0.195} S = 1.16 2297 reflections 111 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained

w = 1/[σ2_(F

o2) + (0.0962P)2 + 0.1961P]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max = 0.001

Δρmax = 0.29 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 F}2_,

conventional R-factors R are based on F, with F set to zero for negative F2_{. The threshold expression of F}2 _{> σ(F}2_{) 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₎

x y z Uiso*/Ueq

O1 0.80092 (10) 0.0913 (2) 0.19525 (10) 0.0411 (3)

C1 0.61872 (12) −0.0341 (3) 0.06097 (12) 0.0296 (3)

O2 0.80864 (11) 0.1179 (2) −0.29558 (10) 0.0436 (4)

C7 1.02083 (14) −0.1997 (3) −0.05480 (13) 0.0330 (4)

H7 1.0352 −0.3370 −0.0923 0.040*

C2 0.56419 (13) 0.1697 (3) 0.08133 (13) 0.0323 (4)

H2 0.6078 0.2862 0.1368 0.039*

C6 0.93984 (12) −0.0249 (3) −0.11728 (13) 0.0307 (4)

C4 0.74619 (13) −0.0645 (3) 0.12672 (13) 0.0321 (4)

C3 0.55359 (13) −0.2037 (3) −0.02102 (13) 0.0325 (4)

H3 0.5901 −0.3431 −0.0356 0.039*

C9 0.87567 (13) −0.0430 (3) −0.24330 (13) 0.0337 (4)

C5 0.80422 (14) −0.2857 (3) 0.10517 (15) 0.0380 (4)

H5A 0.8870 −0.2795 0.1535 0.057*

H5B 0.7927 −0.2883 0.0256 0.057*

H5C 0.7709 −0.4340 0.1223 0.057*

C10 0.89811 (15) −0.2588 (4) −0.30297 (14) 0.0404 (4)

H10A 0.8498 −0.2467 −0.3842 0.061*

H10B 0.8796 −0.4101 −0.2732 0.061*

H10C 0.9796 −0.2606 −0.2905 0.061*

C8 0.91933 (13) 0.1758 (3) −0.06135 (13) 0.0327 (4)

H8 0.8643 0.2961 −0.1029 0.039*

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

O1 0.0345 (6) 0.0419 (7) 0.0406 (7) −0.0040 (5) 0.0087 (5) −0.0049 (5)

C1 0.0306 (7) 0.0301 (8) 0.0282 (7) −0.0004 (5) 0.0121 (6) 0.0030 (5)

O2 0.0499 (7) 0.0420 (7) 0.0338 (6) 0.0051 (5) 0.0117 (5) 0.0036 (5)

C7 0.0346 (7) 0.0314 (8) 0.0333 (8) 0.0011 (6) 0.0140 (6) −0.0040 (6)

supporting information

sup-3 Acta Cryst. (2006). E62, o1582–o1583

C10 0.0443 (9) 0.0452 (10) 0.0322 (8) −0.0009 (7) 0.0160 (7) −0.0063 (7)

C8 0.0325 (7) 0.0315 (8) 0.0324 (8) 0.0025 (6) 0.0115 (6) 0.0009 (6)

Geometric parameters (Å, º)

O1—C4 1.221 (2) C4—C5 1.500 (2)

C1—C2 1.392 (2) C3—C2ii _{1.389 (2)}

C1—C3 1.397 (2) C3—H3 0.95

C1—C4 1.500 (2) C9—C10 1.499 (2)

O2—C9 1.218 (2) C5—H5A 0.98

C7—C8i _{1.387 (2) C5—H5B 0.98}

C7—C6 1.394 (2) C5—H5C 0.98

C7—H7 0.95 C10—H10A 0.98

C2—C3ii _{1.389 (2) C10—H10B 0.98}

C2—H2 0.95 C10—H10C 0.98

C6—C8 1.395 (2) C8—C7i _{1.387 (2)}

C6—C9 1.501 (2) C8—H8 0.95

C2—C1—C3 119.20 (14) O2—C9—C10 121.12 (15)

C2—C1—C4 119.08 (14) O2—C9—C6 120.23 (15)

C3—C1—C4 121.71 (14) C10—C9—C6 118.63 (14)

C8i_{—C7—C6 120.85 (14) C4—C5—H5A 109.5}

C8i_{—C7—H7 119.6 C4—C5—H5B 109.5}

C6—C7—H7 119.6 H5A—C5—H5B 109.5

C3ii_{—C2—C1 120.34 (14) C4—C5—H5C 109.5}

C3ii_{—C2—H2 119.8 H5A—C5—H5C 109.5}

C1—C2—H2 119.8 H5B—C5—H5C 109.5

C7—C6—C8 119.07 (14) C9—C10—H10A 109.5

C7—C6—C9 122.07 (14) C9—C10—H10B 109.5

C8—C6—C9 118.85 (14) H10A—C10—H10B 109.5

O1—C4—C1 119.89 (15) C9—C10—H10C 109.5

O1—C4—C5 121.29 (14) H10A—C10—H10C 109.5

C1—C4—C5 118.82 (13) H10B—C10—H10C 109.5

C2ii_{—C3—C1 120.46 (14) C7}i_{—C8—C6 120.08 (14)}

C2ii_{—C3—H3 119.8 C7}i_{—C8—H8 120.0}

C1—C3—H3 119.8 C6—C8—H8 120.0