14-(4-Fluoro­phen­yl)-14H-dibenzo[a,j]xanthene

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)°.

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

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Computing details

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

Crystal data

C27H17FO	F(000) = 784
Mr = 376.41	Dx = 1.374 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2388 reflections
a = 13.7042 (4) Å	θ = 2.0–27.5°
b = 17.1650 (5) Å	µ = 0.09 mm^−1
c = 7.7369 (2) Å	T = 160 K
V = 1819.97 (9) Å^3	Prism, colourless
Z = 4	0.25 × 0.18 × 0.13 mm

Data collection

Nonius KappaCCD area-detector diffractometer	1743 reflections with I > 2σ(I)
Radiation source: Nonius FR590 sealed tube generator	Rint = 0.083
Horizontally mounted graphite crystal monochromator	θmax = 27.5°, θmin = 2.9°
Detector resolution: 9 pixels mm^-1	h = −17→17
φ and ω scans with κ offsets	k = −22→22
24581 measured reflections	l = −10→10
2230 independent reflections

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)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + (0.0551P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2230 reflections	Δρmax = 0.30 e Å^−3
263 parameters	Δρmin = −0.28 e Å^−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.082 (5)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F1	0.09588 (11)	0.45783 (9)	0.7073 (2)	0.0562 (5)
O10	0.50617 (12)	0.50377 (10)	0.1700 (2)	0.0343 (4)
C1	0.29453 (15)	0.61608 (13)	0.0077 (3)	0.0292 (5)
C2	0.33818 (17)	0.69192 (13)	0.0093 (3)	0.0326 (6)
C3	0.43494 (17)	0.70034 (14)	0.0677 (4)	0.0374 (6)
H3	0.4635	0.7507	0.0707	0.045*
C4	0.48825 (17)	0.63787 (13)	0.1199 (3)	0.0349 (6)
H4	0.5536	0.6443	0.1585	0.042*
C5	0.55694 (17)	0.37441 (14)	0.1328 (3)	0.0352 (6)
H5	0.6196	0.3901	0.1721	0.042*
C6	0.54019 (17)	0.29950 (15)	0.0866 (3)	0.0379 (6)
H6	0.5911	0.2623	0.0979	0.045*
C7	0.44815 (16)	0.27546 (13)	0.0217 (3)	0.0335 (6)
C8	0.37054 (16)	0.33081 (13)	0.0146 (3)	0.0291 (5)
C9	0.30733 (15)	0.46997 (12)	0.0795 (3)	0.0274 (5)
H9	0.2620	0.4615	−0.0200	0.033*
C11	0.48043 (16)	0.42848 (12)	0.1219 (3)	0.0293 (5)
C12	0.38833 (15)	0.40940 (13)	0.0705 (3)	0.0284 (5)
C13	0.35074 (16)	0.55103 (12)	0.0645 (3)	0.0283 (5)
C14	0.44511 (16)	0.56358 (13)	0.1159 (3)	0.0309 (6)
C15	0.19711 (15)	0.60979 (13)	−0.0501 (3)	0.0324 (6)
H15	0.1670	0.5600	−0.0537	0.039*
C16	0.14510 (19)	0.67383 (14)	−0.1009 (3)	0.0385 (6)
H16	0.0795	0.6679	−0.1384	0.046*
C17	0.18735 (19)	0.74791 (14)	−0.0983 (4)	0.0399 (6)
H17	0.1506	0.7922	−0.1329	0.048*
C18	0.28173 (19)	0.75621 (14)	−0.0458 (3)	0.0391 (6)
H18	0.3104	0.8066	−0.0463	0.047*
C19	0.43151 (19)	0.19875 (15)	−0.0364 (4)	0.0414 (6)
H19	0.4834	0.1620	−0.0327	0.050*
C20	0.34281 (19)	0.17611 (15)	−0.0976 (3)	0.0416 (6)
H20	0.3331	0.1242	−0.1366	0.050*
C21	0.26623 (19)	0.22981 (14)	−0.1025 (3)	0.0377 (6)
H21	0.2042	0.2139	−0.1443	0.045*
C22	0.27922 (16)	0.30494 (14)	−0.0482 (3)	0.0325 (6)
H22	0.2260	0.3403	−0.0526	0.039*
C23	0.24879 (16)	0.46364 (12)	0.2481 (3)	0.0271 (5)
C24	0.29703 (16)	0.46886 (13)	0.4068 (4)	0.0314 (6)
H24	0.3661	0.4737	0.4086	0.038*
C25	0.24639 (17)	0.46710 (14)	0.5612 (4)	0.0354 (6)
H25	0.2797	0.4705	0.6686	0.043*
C26	0.14685 (19)	0.46034 (13)	0.5551 (4)	0.0372 (6)
C27	0.09597 (17)	0.45515 (13)	0.4027 (4)	0.0381 (6)
H27	0.0269	0.4509	0.4028	0.046*
C28	0.14751 (17)	0.45629 (12)	0.2483 (4)	0.0327 (6)
H28	0.1134	0.4520	0.1418	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0548 (10)	0.0651 (11)	0.0487 (10)	−0.0094 (8)	0.0271 (8)	−0.0099 (9)
O10	0.0304 (8)	0.0344 (9)	0.0381 (11)	−0.0018 (6)	−0.0047 (8)	−0.0007 (7)
C1	0.0352 (12)	0.0281 (12)	0.0243 (12)	−0.0032 (9)	0.0031 (10)	0.0004 (10)
C2	0.0390 (13)	0.0314 (12)	0.0274 (13)	−0.0037 (10)	0.0069 (11)	−0.0004 (11)
C3	0.0448 (14)	0.0328 (13)	0.0345 (14)	−0.0114 (11)	0.0066 (13)	−0.0033 (12)
C4	0.0325 (12)	0.0385 (14)	0.0337 (13)	−0.0085 (10)	0.0011 (11)	−0.0024 (12)
C5	0.0296 (12)	0.0414 (14)	0.0347 (13)	0.0002 (10)	−0.0001 (11)	0.0049 (12)
C6	0.0363 (13)	0.0425 (15)	0.0347 (15)	0.0089 (11)	0.0019 (11)	0.0084 (12)
C7	0.0385 (13)	0.0321 (13)	0.0300 (14)	0.0032 (10)	0.0064 (11)	0.0026 (11)
C8	0.0338 (12)	0.0315 (12)	0.0219 (12)	0.0010 (9)	0.0035 (10)	0.0023 (10)
C9	0.0285 (12)	0.0278 (12)	0.0257 (13)	−0.0016 (9)	−0.0026 (10)	0.0006 (10)
C11	0.0306 (12)	0.0303 (13)	0.0270 (11)	−0.0025 (10)	0.0014 (10)	−0.0020 (11)
C12	0.0314 (11)	0.0312 (12)	0.0226 (11)	−0.0003 (9)	0.0018 (10)	0.0019 (10)
C13	0.0308 (11)	0.0283 (12)	0.0258 (11)	−0.0024 (9)	0.0040 (10)	0.0013 (10)
C14	0.0335 (12)	0.0319 (13)	0.0274 (12)	0.0001 (10)	0.0004 (11)	−0.0007 (11)
C15	0.0355 (13)	0.0293 (12)	0.0326 (14)	−0.0017 (10)	−0.0002 (11)	0.0011 (11)
C16	0.0447 (14)	0.0349 (14)	0.0360 (14)	0.0035 (11)	−0.0036 (12)	0.0046 (12)
C17	0.0534 (16)	0.0336 (14)	0.0325 (14)	0.0057 (11)	0.0007 (12)	0.0040 (12)
C18	0.0563 (16)	0.0275 (13)	0.0334 (15)	−0.0035 (11)	0.0045 (13)	0.0024 (11)
C19	0.0529 (15)	0.0327 (13)	0.0386 (16)	0.0080 (12)	0.0063 (13)	0.0005 (12)
C20	0.0584 (16)	0.0310 (13)	0.0356 (14)	−0.0034 (12)	0.0003 (14)	−0.0039 (12)
C21	0.0471 (14)	0.0350 (14)	0.0309 (13)	−0.0033 (11)	0.0010 (12)	−0.0028 (12)
C22	0.0355 (12)	0.0325 (13)	0.0295 (14)	−0.0001 (10)	0.0009 (11)	−0.0018 (11)
C23	0.0270 (12)	0.0214 (13)	0.0328 (13)	0.0002 (9)	0.0007 (10)	0.0008 (10)
C24	0.0284 (12)	0.0339 (13)	0.0319 (14)	−0.0041 (9)	−0.0007 (11)	−0.0002 (12)
C25	0.0386 (14)	0.0357 (15)	0.0320 (14)	−0.0059 (11)	0.0040 (12)	−0.0033 (12)
C26	0.0421 (14)	0.0320 (13)	0.0375 (14)	−0.0017 (11)	0.0161 (13)	−0.0033 (12)
C27	0.0300 (13)	0.0305 (14)	0.0536 (17)	−0.0012 (10)	0.0076 (13)	−0.0007 (13)
C28	0.0300 (12)	0.0286 (13)	0.0394 (14)	0.0005 (10)	−0.0007 (11)	0.0018 (12)

Geometric parameters (Å, º)

F1—C26	1.369 (3)	C13—C14	1.370 (3)
O10—C14	1.389 (3)	C15—C16	1.368 (3)
O10—C11	1.390 (3)	C15—H15	0.9500
C1—C15	1.412 (3)	C16—C17	1.397 (3)
C1—C13	1.426 (3)	C16—H16	0.9500
C1—C2	1.433 (3)	C17—C18	1.363 (3)
C2—C3	1.408 (3)	C17—H17	0.9500
C2—C18	1.414 (3)	C18—H18	0.9500
C3—C4	1.359 (3)	C19—C20	1.361 (4)
C3—H3	0.9500	C19—H19	0.9500
C4—C14	1.406 (3)	C20—C21	1.397 (4)
C4—H4	0.9500	C20—H20	0.9500
C5—C6	1.354 (3)	C21—C22	1.368 (3)
C5—C11	1.403 (3)	C21—H21	0.9500
C5—H5	0.9500	C22—H22	0.9500
C6—C7	1.419 (3)	C23—C28	1.394 (3)
C6—H6	0.9500	C23—C24	1.397 (3)
C7—C19	1.410 (3)	C24—C25	1.382 (4)
C7—C8	1.427 (3)	C24—H24	0.9500
C8—C22	1.414 (3)	C25—C26	1.370 (3)
C8—C12	1.437 (3)	C25—H25	0.9500
C9—C13	1.518 (3)	C26—C27	1.373 (4)
C9—C12	1.523 (3)	C27—C28	1.387 (4)
C9—C23	1.535 (3)	C27—H27	0.9500
C9—H9	1.0000	C28—H28	0.9500
C11—C12	1.363 (3)
C14—O10—C11	116.96 (18)	C16—C15—C1	121.5 (2)
C15—C1—C13	123.26 (19)	C16—C15—H15	119.3
C15—C1—C2	117.8 (2)	C1—C15—H15	119.3
C13—C1—C2	118.89 (19)	C15—C16—C17	120.8 (2)
C3—C2—C18	122.1 (2)	C15—C16—H16	119.6
C3—C2—C1	119.3 (2)	C17—C16—H16	119.6
C18—C2—C1	118.6 (2)	C18—C17—C16	119.5 (2)
C4—C3—C2	121.4 (2)	C18—C17—H17	120.2
C4—C3—H3	119.3	C16—C17—H17	120.2
C2—C3—H3	119.3	C17—C18—C2	121.8 (2)
C3—C4—C14	118.9 (2)	C17—C18—H18	119.1
C3—C4—H4	120.6	C2—C18—H18	119.1
C14—C4—H4	120.6	C20—C19—C7	121.5 (2)
C6—C5—C11	119.1 (2)	C20—C19—H19	119.3
C6—C5—H5	120.5	C7—C19—H19	119.3
C11—C5—H5	120.5	C19—C20—C21	119.5 (2)
C5—C6—C7	121.3 (2)	C19—C20—H20	120.3
C5—C6—H6	119.3	C21—C20—H20	120.3
C7—C6—H6	119.3	C22—C21—C20	121.0 (2)
C19—C7—C6	121.9 (2)	C22—C21—H21	119.5
C19—C7—C8	119.3 (2)	C20—C21—H21	119.5
C6—C7—C8	118.8 (2)	C21—C22—C8	121.1 (2)
C22—C8—C7	117.6 (2)	C21—C22—H22	119.4
C22—C8—C12	123.2 (2)	C8—C22—H22	119.4
C7—C8—C12	119.1 (2)	C28—C23—C24	118.4 (2)
C13—C9—C12	109.68 (17)	C28—C23—C9	121.9 (2)
C13—C9—C23	109.53 (18)	C24—C23—C9	119.66 (18)
C12—C9—C23	111.81 (18)	C25—C24—C23	121.4 (2)
C13—C9—H9	108.6	C25—C24—H24	119.3
C12—C9—H9	108.6	C23—C24—H24	119.3
C23—C9—H9	108.6	C26—C25—C24	118.2 (2)
C12—C11—O10	122.4 (2)	C26—C25—H25	120.9
C12—C11—C5	123.4 (2)	C24—C25—H25	120.9
O10—C11—C5	114.16 (19)	F1—C26—C25	118.8 (2)
C11—C12—C8	118.06 (19)	F1—C26—C27	118.5 (2)
C11—C12—C9	119.84 (19)	C25—C26—C27	122.7 (2)
C8—C12—C9	122.07 (18)	C26—C27—C28	118.7 (2)
C14—C13—C1	118.44 (19)	C26—C27—H27	120.7
C14—C13—C9	119.5 (2)	C28—C27—H27	120.7
C1—C13—C9	121.98 (19)	C27—C28—C23	120.6 (3)
C13—C14—O10	122.68 (19)	C27—C28—H28	119.7
C13—C14—C4	123.1 (2)	C23—C28—H28	119.7
O10—C14—C4	114.2 (2)
C15—C1—C2—C3	179.4 (2)	C23—C9—C13—C1	−79.8 (3)
C13—C1—C2—C3	−0.3 (3)	C1—C13—C14—O10	−178.7 (2)
C15—C1—C2—C18	0.3 (3)	C9—C13—C14—O10	4.8 (3)
C13—C1—C2—C18	−179.5 (2)	C1—C13—C14—C4	1.9 (4)
C18—C2—C3—C4	−179.9 (3)	C9—C13—C14—C4	−174.5 (2)
C1—C2—C3—C4	1.1 (4)	C11—O10—C14—C13	19.3 (3)
C2—C3—C4—C14	−0.3 (4)	C11—O10—C14—C4	−161.2 (2)
C11—C5—C6—C7	2.3 (4)	C3—C4—C14—C13	−1.2 (4)
C5—C6—C7—C19	176.2 (2)	C3—C4—C14—O10	179.3 (2)
C5—C6—C7—C8	−3.6 (4)	C13—C1—C15—C16	178.9 (2)
C19—C7—C8—C22	1.2 (3)	C2—C1—C15—C16	−0.8 (3)
C6—C7—C8—C22	−179.0 (2)	C1—C15—C16—C17	0.4 (4)
C19—C7—C8—C12	−178.7 (2)	C15—C16—C17—C18	0.5 (4)
C6—C7—C8—C12	1.1 (3)	C16—C17—C18—C2	−1.1 (4)
C14—O10—C11—C12	−19.0 (3)	C3—C2—C18—C17	−178.4 (3)
C14—O10—C11—C5	161.6 (2)	C1—C2—C18—C17	0.7 (4)
C6—C5—C11—C12	1.6 (4)	C6—C7—C19—C20	179.6 (3)
C6—C5—C11—O10	−179.1 (2)	C8—C7—C19—C20	−0.6 (4)
O10—C11—C12—C8	176.8 (2)	C7—C19—C20—C21	−0.3 (4)
C5—C11—C12—C8	−4.0 (4)	C19—C20—C21—C22	0.5 (4)
O10—C11—C12—C9	−5.4 (3)	C20—C21—C22—C8	0.1 (4)
C5—C11—C12—C9	173.9 (2)	C7—C8—C22—C21	−1.0 (4)
C22—C8—C12—C11	−177.4 (2)	C12—C8—C22—C21	178.9 (2)
C7—C8—C12—C11	2.5 (3)	C13—C9—C23—C28	111.8 (2)
C22—C8—C12—C9	4.8 (3)	C12—C9—C23—C28	−126.4 (2)
C7—C8—C12—C9	−175.3 (2)	C13—C9—C23—C24	−65.3 (2)
C13—C9—C12—C11	26.9 (3)	C12—C9—C23—C24	56.5 (3)
C23—C9—C12—C11	−94.8 (2)	C28—C23—C24—C25	−0.2 (3)
C13—C9—C12—C8	−155.3 (2)	C9—C23—C24—C25	176.9 (2)
C23—C9—C12—C8	82.9 (3)	C23—C24—C25—C26	−0.2 (3)
C15—C1—C13—C14	179.2 (2)	C24—C25—C26—F1	179.4 (2)
C2—C1—C13—C14	−1.1 (3)	C24—C25—C26—C27	0.1 (4)
C15—C1—C13—C9	−4.5 (4)	F1—C26—C27—C28	−178.9 (2)
C2—C1—C13—C9	175.3 (2)	C25—C26—C27—C28	0.4 (3)
C12—C9—C13—C14	−26.5 (3)	C26—C27—C28—C23	−0.9 (3)
C23—C9—C13—C14	96.5 (2)	C24—C23—C28—C27	0.8 (3)
C12—C9—C13—C1	157.2 (2)	C9—C23—C28—C27	−176.31 (19)