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The title compound, C22H16O, was prepared from anthrone and 2-methyl­benz­aldehyde. The central six-membered ring has an asymmetric boat conformation, in which the carbonyl carbon and the opposite carbon deviate from the plane of the ring by 0.124 (3) and 0.283 (2) Å, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804014709/lh6233sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804014709/lh6233Isup2.hkl
Contains datablock I

CCDC reference: 227475

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.056
  • wR factor = 0.171
  • Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
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 1 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: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

10-(2-methylbenzylidene)anthrone top
Crystal data top
C22H16OZ = 2
Mr = 296.35F(000) = 312
Triclinic, P1Dx = 1.263 Mg m3
Hall symbol: -P 1Melting point = 363–366 K
a = 7.0137 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.3135 (4) ÅCell parameters from 25 reflections
c = 11.5107 (5) Åθ = 2.4–27.4°
α = 107.020 (5)°µ = 0.08 mm1
β = 91.224 (4)°T = 293 K
γ = 100.854 (8)°Chunk, yellow
V = 779.33 (6) Å30.41 × 0.31 × 0.28 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3438 independent reflections
Radiation source: fine-focus sealed tube2503 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω/2–θ scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 99
Tmin = 0.972, Tmax = 0.979k = 1313
5264 measured reflectionsl = 1414
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)] = 0.056H-atom parameters constrained
wR(F2) = 0.171 w = 1/[σ2(Fo2) + (0.1018P)2 + 0.0246P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
3438 reflectionsΔρmax = 0.32 e Å3
210 parametersΔρmin = 0.29 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.061 (10)
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
O10.2292 (2)0.66826 (14)0.40091 (11)0.0691 (4)
C10.3235 (2)0.74692 (16)0.72480 (14)0.0445 (4)
C20.4094 (3)0.85931 (18)0.82410 (16)0.0582 (5)
H20.42420.84660.90030.070*
C30.4724 (3)0.98833 (19)0.81128 (17)0.0683 (6)
H30.53151.06150.87830.082*
C40.4488 (3)1.01036 (19)0.69975 (18)0.0643 (5)
H40.48711.09870.69210.077*
C50.3687 (3)0.90134 (18)0.60069 (16)0.0550 (4)
H50.35240.91580.52540.066*
C60.3114 (2)0.76899 (16)0.61114 (14)0.0449 (4)
C70.2543 (2)0.65021 (18)0.49927 (14)0.0480 (4)
C80.2446 (2)0.51083 (16)0.51144 (14)0.0447 (4)
C90.2269 (2)0.39863 (19)0.40572 (15)0.0547 (4)
H90.21950.41310.32980.066*
C100.2203 (3)0.2681 (2)0.41258 (18)0.0629 (5)
H100.20640.19370.34180.075*
C110.2344 (3)0.24716 (19)0.52520 (18)0.0628 (5)
H110.23210.15840.53000.075*
C120.2517 (3)0.35615 (18)0.63039 (17)0.0554 (4)
H120.26220.34040.70560.067*
C130.2537 (2)0.49013 (16)0.62569 (14)0.0438 (4)
C140.2540 (2)0.60763 (16)0.73635 (14)0.0445 (4)
C150.1792 (3)0.58418 (17)0.83613 (14)0.0510 (4)
H150.16100.49280.83690.061*
C160.1215 (2)0.68109 (16)0.94493 (14)0.0474 (4)
C170.0019 (3)0.76635 (18)0.93121 (16)0.0583 (5)
H170.03490.76980.85360.070*
C180.0772 (3)0.84646 (19)1.03043 (18)0.0641 (5)
H180.16130.90251.01970.077*
C190.0269 (3)0.84267 (19)1.14479 (17)0.0629 (5)
H190.07680.89651.21220.075*
C200.0969 (3)0.75957 (18)1.15996 (15)0.0549 (5)
H200.13030.75831.23820.066*
C210.1732 (2)0.67764 (16)1.06202 (15)0.0475 (4)
C220.3104 (3)0.5899 (2)1.08140 (18)0.0672 (5)
H22A0.31720.59221.16540.101*
H22B0.43750.62491.06050.101*
H22C0.26470.49621.03070.101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0851 (10)0.0822 (9)0.0430 (7)0.0140 (7)0.0011 (6)0.0258 (6)
C10.0415 (8)0.0506 (9)0.0389 (8)0.0031 (6)0.0079 (6)0.0130 (6)
C20.0649 (11)0.0607 (10)0.0403 (9)0.0065 (8)0.0080 (8)0.0138 (7)
C30.0787 (14)0.0568 (11)0.0535 (11)0.0100 (9)0.0148 (10)0.0067 (8)
C40.0730 (13)0.0507 (10)0.0668 (12)0.0024 (9)0.0204 (10)0.0195 (9)
C50.0579 (11)0.0598 (10)0.0546 (10)0.0119 (8)0.0154 (8)0.0275 (8)
C60.0389 (8)0.0546 (9)0.0427 (8)0.0075 (6)0.0083 (6)0.0178 (7)
C70.0416 (9)0.0647 (10)0.0390 (8)0.0094 (7)0.0050 (7)0.0185 (7)
C80.0342 (8)0.0569 (9)0.0404 (8)0.0083 (6)0.0043 (6)0.0109 (7)
C90.0458 (10)0.0692 (11)0.0429 (9)0.0118 (8)0.0024 (7)0.0075 (8)
C100.0567 (11)0.0628 (11)0.0582 (11)0.0174 (8)0.0055 (9)0.0016 (8)
C110.0613 (12)0.0534 (10)0.0717 (13)0.0175 (8)0.0103 (10)0.0120 (9)
C120.0554 (11)0.0598 (10)0.0539 (10)0.0148 (8)0.0083 (8)0.0193 (8)
C130.0355 (8)0.0525 (9)0.0422 (8)0.0076 (6)0.0060 (6)0.0132 (7)
C140.0439 (8)0.0504 (9)0.0382 (8)0.0049 (6)0.0035 (6)0.0148 (6)
C150.0626 (11)0.0459 (9)0.0447 (9)0.0058 (7)0.0104 (8)0.0170 (7)
C160.0552 (10)0.0448 (8)0.0413 (8)0.0003 (7)0.0099 (7)0.0174 (6)
C170.0739 (12)0.0566 (10)0.0485 (10)0.0108 (9)0.0074 (9)0.0237 (8)
C180.0710 (13)0.0582 (11)0.0701 (12)0.0196 (9)0.0159 (10)0.0253 (9)
C190.0726 (13)0.0584 (11)0.0556 (11)0.0120 (9)0.0223 (9)0.0137 (8)
C200.0605 (11)0.0619 (10)0.0404 (9)0.0031 (8)0.0113 (8)0.0179 (7)
C210.0478 (9)0.0500 (9)0.0454 (9)0.0017 (7)0.0101 (7)0.0203 (7)
C220.0658 (12)0.0833 (13)0.0611 (11)0.0216 (10)0.0085 (10)0.0305 (10)
Geometric parameters (Å, º) top
O1—C71.2143 (18)C11—H110.9300
C1—C21.395 (2)C12—C131.396 (2)
C1—C61.396 (2)C12—H120.9300
C1—C141.473 (2)C13—C141.479 (2)
C2—C31.373 (2)C14—C151.339 (2)
C2—H20.9300C15—C161.474 (2)
C3—C41.379 (3)C15—H150.9300
C3—H30.9300C16—C171.382 (2)
C4—C51.365 (3)C16—C211.400 (2)
C4—H40.9300C17—C181.380 (3)
C5—C61.389 (2)C17—H170.9300
C5—H50.9300C18—C191.369 (3)
C6—C71.480 (2)C18—H180.9300
C7—C81.474 (2)C19—C201.371 (3)
C8—C131.395 (2)C19—H190.9300
C8—C91.397 (2)C20—C211.382 (2)
C9—C101.363 (3)C20—H200.9300
C9—H90.9300C21—C221.494 (3)
C10—C111.380 (3)C22—H22A0.9600
C10—H100.9300C22—H22B0.9600
C11—C121.375 (2)C22—H22C0.9600
C2—C1—C6117.66 (15)C13—C12—H12119.6
C2—C1—C14122.10 (14)C8—C13—C12118.10 (15)
C6—C1—C14120.20 (14)C8—C13—C14119.42 (14)
C3—C2—C1121.09 (16)C12—C13—C14122.39 (14)
C3—C2—H2119.5C15—C14—C1123.81 (15)
C1—C2—H2119.5C15—C14—C13119.85 (15)
C2—C3—C4120.56 (17)C1—C14—C13116.13 (13)
C2—C3—H3119.7C14—C15—C16129.89 (15)
C4—C3—H3119.7C14—C15—H15115.1
C5—C4—C3119.39 (17)C16—C15—H15115.1
C5—C4—H4120.3C17—C16—C21119.27 (16)
C3—C4—H4120.3C17—C16—C15119.64 (15)
C4—C5—C6120.74 (17)C21—C16—C15120.74 (15)
C4—C5—H5119.6C18—C17—C16121.24 (16)
C6—C5—H5119.6C18—C17—H17119.4
C5—C6—C1120.36 (15)C16—C17—H17119.4
C5—C6—C7119.15 (14)C19—C18—C17119.41 (18)
C1—C6—C7120.26 (14)C19—C18—H18120.3
O1—C7—C8121.85 (15)C17—C18—H18120.3
O1—C7—C6120.93 (16)C18—C19—C20120.02 (17)
C8—C7—C6117.05 (13)C18—C19—H19120.0
C13—C8—C9120.13 (16)C20—C19—H19120.0
C13—C8—C7121.21 (14)C19—C20—C21121.71 (16)
C9—C8—C7118.66 (15)C19—C20—H20119.1
C10—C9—C8120.69 (17)C21—C20—H20119.1
C10—C9—H9119.7C20—C21—C16118.34 (16)
C8—C9—H9119.7C20—C21—C22120.56 (15)
C9—C10—C11119.59 (17)C16—C21—C22121.08 (16)
C9—C10—H10120.2C21—C22—H22A109.5
C11—C10—H10120.2C21—C22—H22B109.5
C12—C11—C10120.64 (18)H22A—C22—H22B109.5
C12—C11—H11119.7C21—C22—H22C109.5
C10—C11—H11119.7H22A—C22—H22C109.5
C11—C12—C13120.80 (17)H22B—C22—H22C109.5
C11—C12—H12119.6
C6—C1—C2—C32.6 (3)C7—C8—C13—C146.0 (2)
C14—C1—C2—C3179.74 (17)C11—C12—C13—C82.2 (3)
C1—C2—C3—C41.2 (3)C11—C12—C13—C14174.27 (16)
C2—C3—C4—C52.5 (3)C2—C1—C14—C1533.2 (3)
C3—C4—C5—C60.1 (3)C6—C1—C14—C15149.24 (17)
C4—C5—C6—C14.0 (3)C2—C1—C14—C13152.20 (16)
C4—C5—C6—C7170.51 (17)C6—C1—C14—C1325.4 (2)
C2—C1—C6—C55.2 (2)C8—C13—C14—C15150.80 (17)
C14—C1—C6—C5177.12 (15)C12—C13—C14—C1525.6 (2)
C2—C1—C6—C7169.29 (16)C8—C13—C14—C124.1 (2)
C14—C1—C6—C78.4 (2)C12—C13—C14—C1159.52 (15)
C5—C6—C7—O110.9 (2)C1—C14—C15—C1610.2 (3)
C1—C6—C7—O1174.54 (16)C13—C14—C15—C16164.27 (17)
C5—C6—C7—C8164.41 (15)C14—C15—C16—C1751.6 (3)
C1—C6—C7—C810.1 (2)C14—C15—C16—C21135.2 (2)
O1—C7—C8—C13173.38 (16)C21—C16—C17—C180.9 (3)
C6—C7—C8—C1311.4 (2)C15—C16—C17—C18172.34 (17)
O1—C7—C8—C97.0 (2)C16—C17—C18—C190.8 (3)
C6—C7—C8—C9168.31 (14)C17—C18—C19—C200.1 (3)
C13—C8—C9—C100.7 (3)C18—C19—C20—C210.3 (3)
C7—C8—C9—C10179.01 (16)C19—C20—C21—C160.1 (3)
C8—C9—C10—C111.0 (3)C19—C20—C21—C22178.97 (17)
C9—C10—C11—C121.1 (3)C17—C16—C21—C200.5 (2)
C10—C11—C12—C130.6 (3)C15—C16—C21—C20172.71 (15)
C9—C8—C13—C122.2 (2)C17—C16—C21—C22178.35 (17)
C7—C8—C13—C12177.43 (14)C15—C16—C21—C228.5 (3)
C9—C8—C13—C14174.35 (14)
 

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