1,5-Diacetyl­anthracene

The title mol­ecule, C₁₈H₁₄O₂, possesses a crystallographically imposed inversion centre. The carbonyl groups are twisted away from the anthracene mean plane by 21.03 (1)°. The crystal packing is stabilized by C—H...π inter­actions and C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.034
• wR factor = 0.108
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

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Alert level C
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   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
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   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
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Computing details

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

1,5-diacetylanthracene

Crystal data

C18H14O2	F(000) = 276
Mr = 262.29	Dx = 1.376 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.8245 (3) Å	Cell parameters from 5428 reflections
b = 6.2085 (2) Å	θ = 3.3–27.5°
c = 10.8823 (3) Å	µ = 0.09 mm^−1
β = 107.472 (1)°	T = 153 K
V = 633.15 (3) Å^3	Block, yellow
Z = 2	0.40 × 0.35 × 0.14 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	1327 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.025
Graphite monochromator	θmax = 27.5°, θmin = 3.8°
ω scans	h = −12→12
5967 measured reflections	k = −8→8
1445 independent reflections	l = −14→13

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.069P)^2 + 0.198P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
1445 reflections	Δρmax = 0.35 e Å^−3
93 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXL97
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.033 (9)

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
O1	0.14358 (8)	0.14110 (13)	0.36628 (7)	0.0263 (2)
C1	0.57789 (10)	0.69074 (16)	0.50455 (9)	0.0164 (2)
H1	0.6295	0.8208	0.5064	0.020*
C2	0.45663 (10)	0.64994 (15)	0.39979 (9)	0.0159 (2)
C3	0.41660 (11)	0.80048 (16)	0.29567 (9)	0.0183 (3)
H3	0.4679	0.9317	0.3014	0.022*
C4	0.30580 (11)	0.75803 (17)	0.18838 (10)	0.0203 (3)
H4	0.2832	0.8560	0.1181	0.024*
C5	0.22422 (11)	0.56756 (17)	0.18159 (9)	0.0200 (3)
H5	0.1471	0.5406	0.1062	0.024*
C6	0.25323 (10)	0.42049 (16)	0.28068 (9)	0.0171 (2)
C7	0.37525 (10)	0.45566 (15)	0.39354 (9)	0.0152 (2)
C8	0.15277 (10)	0.23605 (17)	0.27077 (9)	0.0183 (3)
C9	0.05500 (12)	0.17535 (18)	0.13957 (10)	0.0239 (3)
H9A	0.0248	0.0252	0.1409	0.029*
H9B	0.1058	0.1921	0.0752	0.029*
H9C	−0.0290	0.2693	0.1175	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0262 (4)	0.0300 (5)	0.0218 (4)	−0.0091 (3)	0.0057 (3)	0.0026 (3)
C1	0.0197 (5)	0.0149 (5)	0.0158 (5)	−0.0014 (3)	0.0070 (4)	−0.0009 (3)
C2	0.0189 (5)	0.0147 (5)	0.0153 (5)	0.0010 (3)	0.0068 (4)	−0.0006 (3)
C3	0.0217 (5)	0.0152 (5)	0.0190 (5)	0.0003 (3)	0.0078 (4)	0.0015 (4)
C4	0.0233 (5)	0.0202 (5)	0.0177 (5)	0.0032 (4)	0.0065 (4)	0.0054 (4)
C5	0.0184 (5)	0.0230 (5)	0.0170 (5)	0.0012 (4)	0.0031 (4)	0.0002 (4)
C6	0.0170 (5)	0.0177 (5)	0.0167 (5)	−0.0002 (4)	0.0056 (4)	−0.0020 (4)
C7	0.0173 (5)	0.0158 (5)	0.0138 (5)	0.0002 (3)	0.0065 (3)	−0.0017 (3)
C8	0.0168 (5)	0.0195 (5)	0.0187 (5)	0.0008 (4)	0.0056 (4)	−0.0017 (4)
C9	0.0234 (5)	0.0248 (5)	0.0201 (5)	−0.0047 (4)	0.0015 (4)	−0.0023 (4)

Geometric parameters (Å, º)

O1—C8	1.2217 (13)	C5—C6	1.3760 (14)
C1—C7^i	1.4006 (13)	C5—H5	0.9500
C1—C2	1.4027 (13)	C6—C7	1.4523 (13)
C1—H1	0.9500	C6—C8	1.4943 (14)
C2—C3	1.4298 (13)	C7—C1^i	1.4006 (13)
C2—C7	1.4374 (13)	C8—C9	1.5098 (14)
C3—C4	1.3618 (14)	C9—H9A	0.9800
C3—H3	0.9500	C9—H9B	0.9800
C4—C5	1.4179 (15)	C9—H9C	0.9800
C4—H4	0.9500
C7^i—C1—C2	121.56 (9)	C5—C6—C7	119.15 (9)
C7^i—C1—H1	119.2	C5—C6—C8	118.36 (9)
C2—C1—H1	119.2	C7—C6—C8	122.40 (9)
C1—C2—C3	119.37 (9)	C1^i—C7—C2	117.47 (9)
C1—C2—C7	120.97 (9)	C1^i—C7—C6	124.31 (9)
C3—C2—C7	119.62 (9)	C2—C7—C6	118.19 (9)
C4—C3—C2	120.78 (9)	O1—C8—C6	121.62 (9)
C4—C3—H3	119.6	O1—C8—C9	119.70 (9)
C2—C3—H3	119.6	C6—C8—C9	118.59 (9)
C3—C4—C5	119.99 (9)	C8—C9—H9A	109.5
C3—C4—H4	120.0	C8—C9—H9B	109.5
C5—C4—H4	120.0	H9A—C9—H9B	109.5
C6—C5—C4	122.12 (9)	C8—C9—H9C	109.5
C6—C5—H5	118.9	H9A—C9—H9C	109.5
C4—C5—H5	118.9	H9B—C9—H9C	109.5
C7^i—C1—C2—C3	−177.47 (9)	C1—C2—C7—C6	−178.28 (8)
C7^i—C1—C2—C7	0.29 (15)	C3—C2—C7—C6	−0.53 (14)
C1—C2—C3—C4	175.14 (9)	C5—C6—C7—C1^i	−174.62 (9)
C7—C2—C3—C4	−2.65 (15)	C8—C6—C7—C1^i	8.73 (15)
C2—C3—C4—C5	3.07 (15)	C5—C6—C7—C2	3.24 (14)
C3—C4—C5—C6	−0.23 (16)	C8—C6—C7—C2	−173.42 (8)
C4—C5—C6—C7	−2.95 (15)	C5—C6—C8—O1	−156.50 (10)
C4—C5—C6—C8	173.84 (9)	C7—C6—C8—O1	20.18 (15)
C1—C2—C7—C1^i	−0.28 (15)	C5—C6—C8—C9	20.03 (14)
C3—C2—C7—C1^i	177.47 (8)	C7—C6—C8—C9	−163.30 (9)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg1^ii	0.95	2.64	3.415 (1)	140
C9—H9C···O1^iii	0.98	2.60	3.478 (1)	150

Symmetry codes: (ii) −x+1, y+1/2, −z+1/2; (iii) −x, y+1/2, −z+1/2.