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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031357/cv2095sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031357/cv2095Isup2.hkl
Contains datablock I

CCDC reference: 620782

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

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

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 top
Crystal data top
C18H14O2F(000) = 276
Mr = 262.29Dx = 1.376 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.8245 (3) ÅCell parameters from 5428 reflections
b = 6.2085 (2) Åθ = 3.3–27.5°
c = 10.8823 (3) ŵ = 0.09 mm1
β = 107.472 (1)°T = 153 K
V = 633.15 (3) Å3Block, yellow
Z = 20.40 × 0.35 × 0.14 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1327 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.025
Graphite monochromatorθmax = 27.5°, θmin = 3.8°
ω scansh = 1212
5967 measured reflectionsk = 88
1445 independent reflectionsl = 1413
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.108 w = 1/[σ2(Fo2) + (0.069P)2 + 0.198P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
1445 reflectionsΔρmax = 0.35 e Å3
93 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL97
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.033 (9)
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
O10.14358 (8)0.14110 (13)0.36628 (7)0.0263 (2)
C10.57789 (10)0.69074 (16)0.50455 (9)0.0164 (2)
H10.62950.82080.50640.020*
C20.45663 (10)0.64994 (15)0.39979 (9)0.0159 (2)
C30.41660 (11)0.80048 (16)0.29567 (9)0.0183 (3)
H30.46790.93170.30140.022*
C40.30580 (11)0.75803 (17)0.18838 (10)0.0203 (3)
H40.28320.85600.11810.024*
C50.22422 (11)0.56756 (17)0.18159 (9)0.0200 (3)
H50.14710.54060.10620.024*
C60.25323 (10)0.42049 (16)0.28068 (9)0.0171 (2)
C70.37525 (10)0.45566 (15)0.39354 (9)0.0152 (2)
C80.15277 (10)0.23605 (17)0.27077 (9)0.0183 (3)
C90.05500 (12)0.17535 (18)0.13957 (10)0.0239 (3)
H9A0.02480.02520.14090.029*
H9B0.10580.19210.07520.029*
H9C0.02900.26930.11750.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0262 (4)0.0300 (5)0.0218 (4)0.0091 (3)0.0057 (3)0.0026 (3)
C10.0197 (5)0.0149 (5)0.0158 (5)0.0014 (3)0.0070 (4)0.0009 (3)
C20.0189 (5)0.0147 (5)0.0153 (5)0.0010 (3)0.0068 (4)0.0006 (3)
C30.0217 (5)0.0152 (5)0.0190 (5)0.0003 (3)0.0078 (4)0.0015 (4)
C40.0233 (5)0.0202 (5)0.0177 (5)0.0032 (4)0.0065 (4)0.0054 (4)
C50.0184 (5)0.0230 (5)0.0170 (5)0.0012 (4)0.0031 (4)0.0002 (4)
C60.0170 (5)0.0177 (5)0.0167 (5)0.0002 (4)0.0056 (4)0.0020 (4)
C70.0173 (5)0.0158 (5)0.0138 (5)0.0002 (3)0.0065 (3)0.0017 (3)
C80.0168 (5)0.0195 (5)0.0187 (5)0.0008 (4)0.0056 (4)0.0017 (4)
C90.0234 (5)0.0248 (5)0.0201 (5)0.0047 (4)0.0015 (4)0.0023 (4)
Geometric parameters (Å, º) top
O1—C81.2217 (13)C5—C61.3760 (14)
C1—C7i1.4006 (13)C5—H50.9500
C1—C21.4027 (13)C6—C71.4523 (13)
C1—H10.9500C6—C81.4943 (14)
C2—C31.4298 (13)C7—C1i1.4006 (13)
C2—C71.4374 (13)C8—C91.5098 (14)
C3—C41.3618 (14)C9—H9A0.9800
C3—H30.9500C9—H9B0.9800
C4—C51.4179 (15)C9—H9C0.9800
C4—H40.9500
C7i—C1—C2121.56 (9)C5—C6—C7119.15 (9)
C7i—C1—H1119.2C5—C6—C8118.36 (9)
C2—C1—H1119.2C7—C6—C8122.40 (9)
C1—C2—C3119.37 (9)C1i—C7—C2117.47 (9)
C1—C2—C7120.97 (9)C1i—C7—C6124.31 (9)
C3—C2—C7119.62 (9)C2—C7—C6118.19 (9)
C4—C3—C2120.78 (9)O1—C8—C6121.62 (9)
C4—C3—H3119.6O1—C8—C9119.70 (9)
C2—C3—H3119.6C6—C8—C9118.59 (9)
C3—C4—C5119.99 (9)C8—C9—H9A109.5
C3—C4—H4120.0C8—C9—H9B109.5
C5—C4—H4120.0H9A—C9—H9B109.5
C6—C5—C4122.12 (9)C8—C9—H9C109.5
C6—C5—H5118.9H9A—C9—H9C109.5
C4—C5—H5118.9H9B—C9—H9C109.5
C7i—C1—C2—C3177.47 (9)C1—C2—C7—C6178.28 (8)
C7i—C1—C2—C70.29 (15)C3—C2—C7—C60.53 (14)
C1—C2—C3—C4175.14 (9)C5—C6—C7—C1i174.62 (9)
C7—C2—C3—C42.65 (15)C8—C6—C7—C1i8.73 (15)
C2—C3—C4—C53.07 (15)C5—C6—C7—C23.24 (14)
C3—C4—C5—C60.23 (16)C8—C6—C7—C2173.42 (8)
C4—C5—C6—C72.95 (15)C5—C6—C8—O1156.50 (10)
C4—C5—C6—C8173.84 (9)C7—C6—C8—O120.18 (15)
C1—C2—C7—C1i0.28 (15)C5—C6—C8—C920.03 (14)
C3—C2—C7—C1i177.47 (8)C7—C6—C8—C9163.30 (9)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···Cg1ii0.952.643.415 (1)140
C9—H9C···O1iii0.982.603.478 (1)150
Symmetry codes: (ii) x+1, y+1/2, z+1/2; (iii) x, y+1/2, z+1/2.
 

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