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The title compound, C22H18O2, contains three benzene rings that are not coplanar as a result of steric strain. The mol­ecules are packed in columns along the a axis in the crystal structure, and classical hydrogen bonds are not found.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805015497/is6070sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805015497/is6070Isup2.hkl
Contains datablock I

CCDC reference: 274442

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.055
  • wR factor = 0.125
  • Data-to-parameter ratio = 15.3

checkCIF/PLATON results

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Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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

4,6-Dibenzoyl-1,3-dimethylbenzene top
Crystal data top
C22H18O2F(000) = 664
Mr = 314.36Dx = 1.226 Mg m3
Monoclinic, P21/nMelting point: 377 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 9.7934 (10) ÅCell parameters from 757 reflections
b = 8.4835 (9) Åθ = 2.3–17.8°
c = 20.509 (2) ŵ = 0.08 mm1
β = 91.098 (2)°T = 293 K
V = 1703.6 (3) Å3Rod, colourless
Z = 40.32 × 0.16 × 0.14 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3340 independent reflections
Radiation source: sealed tube2282 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
φ and ω scansθmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 512
Tmin = 0.97, Tmax = 0.98k = 1010
8907 measured reflectionsl = 2525
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.05P)2 + 0.15P]
where P = (Fo2 + 2Fc2)/3
3340 reflections(Δ/σ)max < 0.001
219 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.13 e Å3
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
C10.64048 (19)0.2616 (2)0.43434 (8)0.0550 (5)
C20.73143 (19)0.3769 (2)0.41570 (9)0.0609 (5)
H20.70150.45960.38930.073*
C30.8666 (2)0.3699 (3)0.43605 (10)0.0753 (6)
H30.92720.44880.42430.090*
C40.9109 (3)0.2450 (3)0.47393 (11)0.0836 (7)
H41.00200.23890.48720.100*
C50.8227 (3)0.1316 (3)0.49174 (11)0.0830 (7)
H50.85430.04790.51720.100*
C60.6867 (2)0.1371 (2)0.47307 (9)0.0697 (6)
H60.62670.05870.48620.084*
C70.7251 (2)0.3564 (2)0.18070 (9)0.0600 (5)
C80.8006 (2)0.4220 (2)0.23183 (10)0.0689 (6)
H80.75610.46420.26750.083*
C90.9413 (2)0.4250 (3)0.23009 (13)0.0825 (7)
H90.99130.46770.26480.099*
C101.0072 (3)0.3658 (3)0.17772 (15)0.0923 (8)
H101.10220.36570.17720.111*
C110.9346 (3)0.3063 (3)0.12588 (14)0.0907 (7)
H110.97990.27020.08930.109*
C120.7937 (2)0.2998 (3)0.12762 (11)0.0761 (6)
H120.74480.25680.09260.091*
C130.31484 (19)0.5292 (2)0.29034 (10)0.0621 (5)
H130.24210.59950.28740.074*
C140.34318 (18)0.4593 (2)0.35039 (9)0.0556 (5)
C150.45344 (17)0.3554 (2)0.35417 (8)0.0505 (4)
C160.52799 (18)0.3271 (2)0.29890 (8)0.0512 (4)
H160.60270.25960.30200.061*
C170.49655 (18)0.3947 (2)0.23909 (8)0.0534 (4)
C180.3880 (2)0.5005 (2)0.23517 (9)0.0583 (5)
C190.4934 (2)0.2716 (2)0.41578 (9)0.0613 (5)
C200.5738 (2)0.3484 (2)0.18093 (9)0.0650 (5)
C210.2571 (2)0.4999 (3)0.40768 (11)0.0851 (7)
H21A0.20240.41040.41900.128*
H21B0.19860.58710.39660.128*
H21C0.31510.52810.44410.128*
C220.3527 (3)0.5875 (3)0.17244 (11)0.0941 (8)
H22A0.43250.64000.15690.141*
H22B0.28260.66380.18050.141*
H22C0.32050.51360.14020.141*
O10.40668 (16)0.2097 (2)0.44949 (8)0.0964 (5)
O20.51280 (18)0.3001 (3)0.13217 (7)0.1133 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0659 (12)0.0554 (10)0.0433 (9)0.0032 (9)0.0060 (8)0.0013 (8)
C20.0613 (11)0.0690 (12)0.0519 (10)0.0055 (10)0.0102 (9)0.0052 (9)
C30.0663 (13)0.0953 (16)0.0639 (12)0.0054 (11)0.0091 (10)0.0016 (11)
C40.0750 (15)0.1082 (19)0.0671 (13)0.0183 (15)0.0119 (11)0.0015 (13)
C50.0969 (18)0.0854 (16)0.0663 (14)0.0211 (14)0.0126 (13)0.0085 (12)
C60.0876 (15)0.0645 (12)0.0568 (11)0.0021 (11)0.0056 (10)0.0053 (9)
C70.0655 (12)0.0577 (11)0.0567 (10)0.0001 (9)0.0009 (9)0.0094 (9)
C80.0620 (13)0.0689 (13)0.0761 (13)0.0073 (10)0.0025 (10)0.0045 (10)
C90.0673 (14)0.0758 (14)0.1044 (19)0.0095 (12)0.0021 (13)0.0074 (13)
C100.0721 (16)0.0822 (16)0.123 (2)0.0085 (13)0.0123 (16)0.0194 (16)
C110.0889 (18)0.0834 (16)0.1007 (19)0.0217 (14)0.0255 (15)0.0114 (14)
C120.0855 (16)0.0698 (13)0.0734 (14)0.0130 (12)0.0091 (12)0.0043 (11)
C130.0499 (11)0.0585 (11)0.0774 (13)0.0033 (9)0.0115 (10)0.0028 (10)
C140.0471 (10)0.0531 (10)0.0666 (11)0.0057 (8)0.0015 (9)0.0145 (9)
C150.0483 (10)0.0507 (9)0.0524 (9)0.0088 (8)0.0027 (8)0.0024 (8)
C160.0501 (10)0.0518 (10)0.0515 (10)0.0023 (8)0.0074 (8)0.0016 (8)
C170.0530 (10)0.0571 (10)0.0496 (10)0.0049 (8)0.0112 (8)0.0026 (8)
C180.0562 (11)0.0561 (10)0.0620 (11)0.0062 (9)0.0130 (9)0.0040 (9)
C190.0633 (12)0.0662 (12)0.0543 (10)0.0121 (10)0.0011 (9)0.0024 (9)
C200.0683 (13)0.0754 (13)0.0511 (10)0.0037 (11)0.0066 (9)0.0018 (10)
C210.0671 (14)0.1011 (17)0.0876 (16)0.0029 (12)0.0137 (12)0.0244 (13)
C220.0947 (18)0.0956 (17)0.0910 (17)0.0085 (14)0.0241 (14)0.0302 (14)
O10.0786 (11)0.1273 (14)0.0834 (11)0.0243 (10)0.0053 (9)0.0328 (10)
O20.0931 (12)0.1830 (18)0.0632 (9)0.0093 (13)0.0150 (9)0.0354 (11)
Geometric parameters (Å, º) top
C1—C21.382 (3)C11—H110.9300
C1—C61.392 (3)C12—H120.9300
C1—C191.485 (3)C13—C181.373 (3)
C2—C31.382 (3)C13—C141.390 (3)
C2—H20.9300C13—H130.9300
C3—C41.379 (3)C14—C151.395 (2)
C3—H30.9300C14—C211.499 (3)
C4—C51.347 (3)C15—C161.381 (2)
C4—H40.9300C15—C191.496 (2)
C5—C61.380 (3)C16—C171.383 (2)
C5—H50.9300C16—H160.9300
C6—H60.9300C17—C181.393 (3)
C7—C121.377 (3)C17—C201.478 (3)
C7—C81.388 (3)C18—C221.517 (3)
C7—C201.483 (3)C19—O11.224 (2)
C8—C91.380 (3)C20—O21.225 (2)
C8—H80.9300C21—H21A0.9600
C9—C101.360 (4)C21—H21B0.9600
C9—H90.9300C21—H21C0.9600
C10—C111.364 (4)C22—H22A0.9600
C10—H100.9300C22—H22B0.9600
C11—C121.382 (3)C22—H22C0.9600
C2—C1—C6119.40 (19)C18—C13—C14123.79 (18)
C2—C1—C19121.07 (16)C18—C13—H13118.1
C6—C1—C19119.49 (18)C14—C13—H13118.1
C3—C2—C1120.34 (19)C13—C14—C15117.39 (17)
C3—C2—H2119.8C13—C14—C21119.38 (18)
C1—C2—H2119.8C15—C14—C21123.22 (18)
C4—C3—C2119.5 (2)C16—C15—C14119.02 (16)
C4—C3—H3120.3C16—C15—C19118.48 (16)
C2—C3—H3120.3C14—C15—C19122.49 (17)
C5—C4—C3120.3 (2)C15—C16—C17122.92 (17)
C5—C4—H4119.8C15—C16—H16118.5
C3—C4—H4119.8C17—C16—H16118.5
C4—C5—C6121.4 (2)C16—C17—C18118.37 (18)
C4—C5—H5119.3C16—C17—C20119.80 (17)
C6—C5—H5119.3C18—C17—C20121.78 (16)
C5—C6—C1119.0 (2)C13—C18—C17118.46 (17)
C5—C6—H6120.5C13—C18—C22119.91 (19)
C1—C6—H6120.5C17—C18—C22121.6 (2)
C12—C7—C8118.4 (2)O1—C19—C1120.74 (17)
C12—C7—C20119.31 (19)O1—C19—C15120.52 (18)
C8—C7—C20122.26 (19)C1—C19—C15118.72 (16)
C9—C8—C7120.4 (2)O2—C20—C17119.9 (2)
C9—C8—H8119.8O2—C20—C7119.0 (2)
C7—C8—H8119.8C17—C20—C7121.16 (16)
C10—C9—C8120.2 (2)C14—C21—H21A109.5
C10—C9—H9119.9C14—C21—H21B109.5
C8—C9—H9119.9H21A—C21—H21B109.5
C9—C10—C11120.2 (3)C14—C21—H21C109.5
C9—C10—H10119.9H21A—C21—H21C109.5
C11—C10—H10119.9H21B—C21—H21C109.5
C10—C11—C12120.1 (3)C18—C22—H22A109.5
C10—C11—H11120.0C18—C22—H22B109.5
C12—C11—H11120.0H22A—C22—H22B109.5
C7—C12—C11120.6 (2)C18—C22—H22C109.5
C7—C12—H12119.7H22A—C22—H22C109.5
C11—C12—H12119.7H22B—C22—H22C109.5
 

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