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In the title compound, C27H17FO, the mean plane of the xanthene core is almost perpendicular to that of the the 4-fluoro­phenyl substituent, the dihedral angle being 87.69 (6)°. The xanthene core has a boat conformation, the folding angle between the naphthyl units being 22.54 (4)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045053/lh2229sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045053/lh2229Isup2.hkl
Contains datablock I

CCDC reference: 630054

Key indicators

  • Single-crystal X-ray study
  • T = 160 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.045
  • wR factor = 0.099
  • Data-to-parameter ratio = 8.5

checkCIF/PLATON results

No syntax errors found



Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.47 From the CIF: _reflns_number_total 2230 Count of symmetry unique reflns 2237 Completeness (_total/calc) 99.69% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 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: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

14-(4-Fluorophenyl)-9H-dibenzo[a,j]xanthene top
Crystal data top
C27H17FOF(000) = 784
Mr = 376.41Dx = 1.374 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 2388 reflections
a = 13.7042 (4) Åθ = 2.0–27.5°
b = 17.1650 (5) ŵ = 0.09 mm1
c = 7.7369 (2) ÅT = 160 K
V = 1819.97 (9) Å3Prism, colourless
Z = 40.25 × 0.18 × 0.13 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
1743 reflections with I > 2σ(I)
Radiation source: Nonius FR590 sealed tube generatorRint = 0.083
Horizontally mounted graphite crystal monochromatorθmax = 27.5°, θmin = 2.9°
Detector resolution: 9 pixels mm-1h = 1717
φ and ω scans with κ offsetsk = 2222
24581 measured reflectionsl = 1010
2230 independent reflections
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)] = 0.045H-atom parameters constrained
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0551P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2230 reflectionsΔρmax = 0.30 e Å3
263 parametersΔρmin = 0.28 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.082 (5)
Special details top

Experimental. Solvent used: ? Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.440 (2) Frames collected: 186 Seconds exposure per frame: 36 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 30.0

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
F10.09588 (11)0.45783 (9)0.7073 (2)0.0562 (5)
O100.50617 (12)0.50377 (10)0.1700 (2)0.0343 (4)
C10.29453 (15)0.61608 (13)0.0077 (3)0.0292 (5)
C20.33818 (17)0.69192 (13)0.0093 (3)0.0326 (6)
C30.43494 (17)0.70034 (14)0.0677 (4)0.0374 (6)
H30.46350.75070.07070.045*
C40.48825 (17)0.63787 (13)0.1199 (3)0.0349 (6)
H40.55360.64430.15850.042*
C50.55694 (17)0.37441 (14)0.1328 (3)0.0352 (6)
H50.61960.39010.17210.042*
C60.54019 (17)0.29950 (15)0.0866 (3)0.0379 (6)
H60.59110.26230.09790.045*
C70.44815 (16)0.27546 (13)0.0217 (3)0.0335 (6)
C80.37054 (16)0.33081 (13)0.0146 (3)0.0291 (5)
C90.30733 (15)0.46997 (12)0.0795 (3)0.0274 (5)
H90.26200.46150.02000.033*
C110.48043 (16)0.42848 (12)0.1219 (3)0.0293 (5)
C120.38833 (15)0.40940 (13)0.0705 (3)0.0284 (5)
C130.35074 (16)0.55103 (12)0.0645 (3)0.0283 (5)
C140.44511 (16)0.56358 (13)0.1159 (3)0.0309 (6)
C150.19711 (15)0.60979 (13)0.0501 (3)0.0324 (6)
H150.16700.56000.05370.039*
C160.14510 (19)0.67383 (14)0.1009 (3)0.0385 (6)
H160.07950.66790.13840.046*
C170.18735 (19)0.74791 (14)0.0983 (4)0.0399 (6)
H170.15060.79220.13290.048*
C180.28173 (19)0.75621 (14)0.0458 (3)0.0391 (6)
H180.31040.80660.04630.047*
C190.43151 (19)0.19875 (15)0.0364 (4)0.0414 (6)
H190.48340.16200.03270.050*
C200.34281 (19)0.17611 (15)0.0976 (3)0.0416 (6)
H200.33310.12420.13660.050*
C210.26623 (19)0.22981 (14)0.1025 (3)0.0377 (6)
H210.20420.21390.14430.045*
C220.27922 (16)0.30494 (14)0.0482 (3)0.0325 (6)
H220.22600.34030.05260.039*
C230.24879 (16)0.46364 (12)0.2481 (3)0.0271 (5)
C240.29703 (16)0.46886 (13)0.4068 (4)0.0314 (6)
H240.36610.47370.40860.038*
C250.24639 (17)0.46710 (14)0.5612 (4)0.0354 (6)
H250.27970.47050.66860.043*
C260.14685 (19)0.46034 (13)0.5551 (4)0.0372 (6)
C270.09597 (17)0.45515 (13)0.4027 (4)0.0381 (6)
H270.02690.45090.40280.046*
C280.14751 (17)0.45629 (12)0.2483 (4)0.0327 (6)
H280.11340.45200.14180.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0548 (10)0.0651 (11)0.0487 (10)0.0094 (8)0.0271 (8)0.0099 (9)
O100.0304 (8)0.0344 (9)0.0381 (11)0.0018 (6)0.0047 (8)0.0007 (7)
C10.0352 (12)0.0281 (12)0.0243 (12)0.0032 (9)0.0031 (10)0.0004 (10)
C20.0390 (13)0.0314 (12)0.0274 (13)0.0037 (10)0.0069 (11)0.0004 (11)
C30.0448 (14)0.0328 (13)0.0345 (14)0.0114 (11)0.0066 (13)0.0033 (12)
C40.0325 (12)0.0385 (14)0.0337 (13)0.0085 (10)0.0011 (11)0.0024 (12)
C50.0296 (12)0.0414 (14)0.0347 (13)0.0002 (10)0.0001 (11)0.0049 (12)
C60.0363 (13)0.0425 (15)0.0347 (15)0.0089 (11)0.0019 (11)0.0084 (12)
C70.0385 (13)0.0321 (13)0.0300 (14)0.0032 (10)0.0064 (11)0.0026 (11)
C80.0338 (12)0.0315 (12)0.0219 (12)0.0010 (9)0.0035 (10)0.0023 (10)
C90.0285 (12)0.0278 (12)0.0257 (13)0.0016 (9)0.0026 (10)0.0006 (10)
C110.0306 (12)0.0303 (13)0.0270 (11)0.0025 (10)0.0014 (10)0.0020 (11)
C120.0314 (11)0.0312 (12)0.0226 (11)0.0003 (9)0.0018 (10)0.0019 (10)
C130.0308 (11)0.0283 (12)0.0258 (11)0.0024 (9)0.0040 (10)0.0013 (10)
C140.0335 (12)0.0319 (13)0.0274 (12)0.0001 (10)0.0004 (11)0.0007 (11)
C150.0355 (13)0.0293 (12)0.0326 (14)0.0017 (10)0.0002 (11)0.0011 (11)
C160.0447 (14)0.0349 (14)0.0360 (14)0.0035 (11)0.0036 (12)0.0046 (12)
C170.0534 (16)0.0336 (14)0.0325 (14)0.0057 (11)0.0007 (12)0.0040 (12)
C180.0563 (16)0.0275 (13)0.0334 (15)0.0035 (11)0.0045 (13)0.0024 (11)
C190.0529 (15)0.0327 (13)0.0386 (16)0.0080 (12)0.0063 (13)0.0005 (12)
C200.0584 (16)0.0310 (13)0.0356 (14)0.0034 (12)0.0003 (14)0.0039 (12)
C210.0471 (14)0.0350 (14)0.0309 (13)0.0033 (11)0.0010 (12)0.0028 (12)
C220.0355 (12)0.0325 (13)0.0295 (14)0.0001 (10)0.0009 (11)0.0018 (11)
C230.0270 (12)0.0214 (13)0.0328 (13)0.0002 (9)0.0007 (10)0.0008 (10)
C240.0284 (12)0.0339 (13)0.0319 (14)0.0041 (9)0.0007 (11)0.0002 (12)
C250.0386 (14)0.0357 (15)0.0320 (14)0.0059 (11)0.0040 (12)0.0033 (12)
C260.0421 (14)0.0320 (13)0.0375 (14)0.0017 (11)0.0161 (13)0.0033 (12)
C270.0300 (13)0.0305 (14)0.0536 (17)0.0012 (10)0.0076 (13)0.0007 (13)
C280.0300 (12)0.0286 (13)0.0394 (14)0.0005 (10)0.0007 (11)0.0018 (12)
Geometric parameters (Å, º) top
F1—C261.369 (3)C13—C141.370 (3)
O10—C141.389 (3)C15—C161.368 (3)
O10—C111.390 (3)C15—H150.9500
C1—C151.412 (3)C16—C171.397 (3)
C1—C131.426 (3)C16—H160.9500
C1—C21.433 (3)C17—C181.363 (3)
C2—C31.408 (3)C17—H170.9500
C2—C181.414 (3)C18—H180.9500
C3—C41.359 (3)C19—C201.361 (4)
C3—H30.9500C19—H190.9500
C4—C141.406 (3)C20—C211.397 (4)
C4—H40.9500C20—H200.9500
C5—C61.354 (3)C21—C221.368 (3)
C5—C111.403 (3)C21—H210.9500
C5—H50.9500C22—H220.9500
C6—C71.419 (3)C23—C281.394 (3)
C6—H60.9500C23—C241.397 (3)
C7—C191.410 (3)C24—C251.382 (4)
C7—C81.427 (3)C24—H240.9500
C8—C221.414 (3)C25—C261.370 (3)
C8—C121.437 (3)C25—H250.9500
C9—C131.518 (3)C26—C271.373 (4)
C9—C121.523 (3)C27—C281.387 (4)
C9—C231.535 (3)C27—H270.9500
C9—H91.0000C28—H280.9500
C11—C121.363 (3)
C14—O10—C11116.96 (18)C16—C15—C1121.5 (2)
C15—C1—C13123.26 (19)C16—C15—H15119.3
C15—C1—C2117.8 (2)C1—C15—H15119.3
C13—C1—C2118.89 (19)C15—C16—C17120.8 (2)
C3—C2—C18122.1 (2)C15—C16—H16119.6
C3—C2—C1119.3 (2)C17—C16—H16119.6
C18—C2—C1118.6 (2)C18—C17—C16119.5 (2)
C4—C3—C2121.4 (2)C18—C17—H17120.2
C4—C3—H3119.3C16—C17—H17120.2
C2—C3—H3119.3C17—C18—C2121.8 (2)
C3—C4—C14118.9 (2)C17—C18—H18119.1
C3—C4—H4120.6C2—C18—H18119.1
C14—C4—H4120.6C20—C19—C7121.5 (2)
C6—C5—C11119.1 (2)C20—C19—H19119.3
C6—C5—H5120.5C7—C19—H19119.3
C11—C5—H5120.5C19—C20—C21119.5 (2)
C5—C6—C7121.3 (2)C19—C20—H20120.3
C5—C6—H6119.3C21—C20—H20120.3
C7—C6—H6119.3C22—C21—C20121.0 (2)
C19—C7—C6121.9 (2)C22—C21—H21119.5
C19—C7—C8119.3 (2)C20—C21—H21119.5
C6—C7—C8118.8 (2)C21—C22—C8121.1 (2)
C22—C8—C7117.6 (2)C21—C22—H22119.4
C22—C8—C12123.2 (2)C8—C22—H22119.4
C7—C8—C12119.1 (2)C28—C23—C24118.4 (2)
C13—C9—C12109.68 (17)C28—C23—C9121.9 (2)
C13—C9—C23109.53 (18)C24—C23—C9119.66 (18)
C12—C9—C23111.81 (18)C25—C24—C23121.4 (2)
C13—C9—H9108.6C25—C24—H24119.3
C12—C9—H9108.6C23—C24—H24119.3
C23—C9—H9108.6C26—C25—C24118.2 (2)
C12—C11—O10122.4 (2)C26—C25—H25120.9
C12—C11—C5123.4 (2)C24—C25—H25120.9
O10—C11—C5114.16 (19)F1—C26—C25118.8 (2)
C11—C12—C8118.06 (19)F1—C26—C27118.5 (2)
C11—C12—C9119.84 (19)C25—C26—C27122.7 (2)
C8—C12—C9122.07 (18)C26—C27—C28118.7 (2)
C14—C13—C1118.44 (19)C26—C27—H27120.7
C14—C13—C9119.5 (2)C28—C27—H27120.7
C1—C13—C9121.98 (19)C27—C28—C23120.6 (3)
C13—C14—O10122.68 (19)C27—C28—H28119.7
C13—C14—C4123.1 (2)C23—C28—H28119.7
O10—C14—C4114.2 (2)
C15—C1—C2—C3179.4 (2)C23—C9—C13—C179.8 (3)
C13—C1—C2—C30.3 (3)C1—C13—C14—O10178.7 (2)
C15—C1—C2—C180.3 (3)C9—C13—C14—O104.8 (3)
C13—C1—C2—C18179.5 (2)C1—C13—C14—C41.9 (4)
C18—C2—C3—C4179.9 (3)C9—C13—C14—C4174.5 (2)
C1—C2—C3—C41.1 (4)C11—O10—C14—C1319.3 (3)
C2—C3—C4—C140.3 (4)C11—O10—C14—C4161.2 (2)
C11—C5—C6—C72.3 (4)C3—C4—C14—C131.2 (4)
C5—C6—C7—C19176.2 (2)C3—C4—C14—O10179.3 (2)
C5—C6—C7—C83.6 (4)C13—C1—C15—C16178.9 (2)
C19—C7—C8—C221.2 (3)C2—C1—C15—C160.8 (3)
C6—C7—C8—C22179.0 (2)C1—C15—C16—C170.4 (4)
C19—C7—C8—C12178.7 (2)C15—C16—C17—C180.5 (4)
C6—C7—C8—C121.1 (3)C16—C17—C18—C21.1 (4)
C14—O10—C11—C1219.0 (3)C3—C2—C18—C17178.4 (3)
C14—O10—C11—C5161.6 (2)C1—C2—C18—C170.7 (4)
C6—C5—C11—C121.6 (4)C6—C7—C19—C20179.6 (3)
C6—C5—C11—O10179.1 (2)C8—C7—C19—C200.6 (4)
O10—C11—C12—C8176.8 (2)C7—C19—C20—C210.3 (4)
C5—C11—C12—C84.0 (4)C19—C20—C21—C220.5 (4)
O10—C11—C12—C95.4 (3)C20—C21—C22—C80.1 (4)
C5—C11—C12—C9173.9 (2)C7—C8—C22—C211.0 (4)
C22—C8—C12—C11177.4 (2)C12—C8—C22—C21178.9 (2)
C7—C8—C12—C112.5 (3)C13—C9—C23—C28111.8 (2)
C22—C8—C12—C94.8 (3)C12—C9—C23—C28126.4 (2)
C7—C8—C12—C9175.3 (2)C13—C9—C23—C2465.3 (2)
C13—C9—C12—C1126.9 (3)C12—C9—C23—C2456.5 (3)
C23—C9—C12—C1194.8 (2)C28—C23—C24—C250.2 (3)
C13—C9—C12—C8155.3 (2)C9—C23—C24—C25176.9 (2)
C23—C9—C12—C882.9 (3)C23—C24—C25—C260.2 (3)
C15—C1—C13—C14179.2 (2)C24—C25—C26—F1179.4 (2)
C2—C1—C13—C141.1 (3)C24—C25—C26—C270.1 (4)
C15—C1—C13—C94.5 (4)F1—C26—C27—C28178.9 (2)
C2—C1—C13—C9175.3 (2)C25—C26—C27—C280.4 (3)
C12—C9—C13—C1426.5 (3)C26—C27—C28—C230.9 (3)
C23—C9—C13—C1496.5 (2)C24—C23—C28—C270.8 (3)
C12—C9—C13—C1157.2 (2)C9—C23—C28—C27176.31 (19)
 

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