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The title compound, C20H16O, (I), whose 9-aryl group is freely rotating in solution, crystallizes exclusively as its sp rotamer, which exhibits intermolecular hydrogen bonding involving O—H...π(fluorene) but not involving O—H...OH. The mol­ecules pack as centrosymmetric dimers incorporating two O—H...π(fluorene) hydrogen bonds. Although (I) melted sharply without decomposition, its melt failed to recrystallize on cooling.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803016465/lh6091sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803016465/lh6091Isup2.hkl
Contains datablock I

CCDC reference: 221719

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.045
  • wR factor = 0.142
  • Data-to-parameter ratio = 13.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
PLAT_420 Alert B D-H Without Acceptor O1 - H1 ... ?
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
0 Alert Level C = Please check

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,1996); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: PROCESS in TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: SIR92 (Burla et al., 1989); program(s) used to refine structure: LS in TEXSAN and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2000); software used to prepare material for publication: TEXSAN, SHELXL97 and PLATON (Spek, 2000).

sp-9-(meta-Methylphenyl)-9-fluorenol top
Crystal data top
C20H16OF(000) = 576
Mr = 272.33Dx = 1.227 Mg m3
Monoclinic, P21/cMelting point = 353–354.5 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71069 Å
a = 9.1443 (12) ÅCell parameters from 25 reflections
b = 19.4498 (14) Åθ = 16.0–20.0°
c = 8.6651 (10) ŵ = 0.07 mm1
β = 106.989 (9)°T = 296 K
V = 1473.9 (3) Å3Prism, colorless
Z = 40.42 × 0.34 × 0.21 mm
Data collection top
Rigaku AFC-5S
diffractometer
Rint = 0.027
Radiation source: fine-focus sealed tubeθmax = 25.1°, θmin = 2.1°
Graphite monochromatorh = 1010
ω scansk = 230
2804 measured reflectionsl = 010
2620 independent reflections3 standard reflections every 100 reflections
1500 reflections with I > 2σ(I) intensity decay: 0.3%
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0675P)2 + 0.2168P]
where P = (Fo2 + 2Fc2)/3
2620 reflections(Δ/σ)max < 0.001
192 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.23 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.10298 (18)0.00523 (8)0.2586 (2)0.0512 (5)
C10.1807 (3)0.09719 (14)0.0067 (3)0.0554 (7)
C20.1491 (4)0.12771 (16)0.1570 (3)0.0662 (8)
C30.0207 (4)0.16684 (15)0.2171 (3)0.0632 (8)
C40.0837 (3)0.17597 (13)0.1309 (3)0.0545 (7)
C4A0.0543 (3)0.14437 (11)0.0189 (3)0.0424 (6)
C4B0.1444 (2)0.14244 (11)0.1346 (3)0.0407 (5)
C50.2856 (3)0.17036 (13)0.1281 (3)0.0523 (7)
C60.3456 (3)0.15831 (14)0.2540 (4)0.0593 (7)
C70.2665 (3)0.11959 (14)0.3852 (4)0.0597 (7)
C80.1246 (3)0.09167 (12)0.3934 (3)0.0497 (6)
C8A0.0655 (2)0.10306 (11)0.2670 (3)0.0389 (5)
C90.0870 (2)0.07817 (11)0.2486 (3)0.0388 (5)
C9A0.0781 (3)0.10594 (11)0.0806 (3)0.0420 (6)
C100.2204 (2)0.10891 (11)0.3800 (3)0.0393 (5)
C110.3135 (2)0.06873 (13)0.5003 (3)0.0431 (6)
C120.4306 (3)0.09697 (13)0.6247 (3)0.0472 (6)
C130.4527 (3)0.16708 (14)0.6255 (3)0.0572 (7)
C140.3608 (3)0.20789 (14)0.5061 (3)0.0652 (8)
C150.2459 (3)0.17908 (13)0.3833 (3)0.0562 (7)
C160.5280 (3)0.05209 (16)0.7574 (3)0.0736 (9)
H10.02840.01280.19490.077*
H1A0.26910.07140.03440.066*
H20.21630.12150.21830.079*
H30.00320.18770.31750.076*
H40.17100.20250.17210.065*
H50.33890.19680.04010.063*
H60.44050.17650.25050.071*
H70.30870.11210.46930.072*
H80.07090.06590.48230.060*
H110.29760.02150.49810.052*
H130.53050.18700.70740.069*
H140.37630.25520.50860.078*
H150.18540.20690.30230.067*
H16A0.63320.05590.75930.110*
H16B0.49560.00510.73800.110*
H16C0.51730.06670.85940.110*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0501 (10)0.0365 (9)0.0585 (11)0.0011 (7)0.0027 (8)0.0035 (8)
C10.0515 (15)0.0622 (17)0.0556 (16)0.0043 (12)0.0207 (13)0.0106 (14)
C20.076 (2)0.077 (2)0.0561 (18)0.0196 (17)0.0354 (16)0.0135 (15)
C30.083 (2)0.0684 (19)0.0396 (15)0.0247 (16)0.0208 (15)0.0035 (13)
C40.0621 (16)0.0536 (15)0.0414 (15)0.0054 (12)0.0049 (12)0.0038 (12)
C4A0.0438 (13)0.0425 (13)0.0365 (12)0.0049 (10)0.0048 (10)0.0026 (10)
C4B0.0371 (12)0.0439 (13)0.0365 (12)0.0025 (10)0.0034 (10)0.0049 (11)
C50.0413 (14)0.0573 (15)0.0523 (16)0.0068 (12)0.0040 (12)0.0013 (13)
C60.0428 (14)0.0646 (18)0.074 (2)0.0041 (13)0.0226 (14)0.0052 (15)
C70.0593 (17)0.0630 (17)0.0639 (18)0.0038 (13)0.0295 (14)0.0022 (14)
C80.0516 (15)0.0527 (15)0.0449 (14)0.0019 (12)0.0145 (12)0.0041 (12)
C8A0.0372 (12)0.0397 (12)0.0368 (13)0.0038 (10)0.0062 (10)0.0027 (10)
C90.0382 (12)0.0348 (12)0.0408 (13)0.0014 (10)0.0074 (10)0.0002 (10)
C9A0.0415 (13)0.0424 (13)0.0405 (13)0.0062 (10)0.0095 (11)0.0062 (10)
C100.0348 (12)0.0412 (13)0.0402 (13)0.0005 (10)0.0080 (10)0.0038 (10)
C110.0413 (13)0.0436 (13)0.0437 (13)0.0026 (10)0.0109 (10)0.0032 (11)
C120.0376 (13)0.0620 (16)0.0411 (13)0.0067 (11)0.0101 (11)0.0060 (12)
C130.0424 (14)0.0662 (18)0.0553 (16)0.0075 (12)0.0023 (12)0.0128 (14)
C140.0588 (17)0.0480 (16)0.076 (2)0.0108 (13)0.0011 (15)0.0072 (14)
C150.0509 (15)0.0435 (14)0.0620 (17)0.0027 (12)0.0025 (13)0.0032 (13)
C160.0671 (19)0.082 (2)0.0559 (18)0.0171 (16)0.0064 (15)0.0006 (16)
Geometric parameters (Å, º) top
O1—C91.426 (3)C12—C131.378 (4)
C1—C9A1.377 (3)C12—C161.510 (3)
C1—C21.382 (4)C13—C141.378 (4)
C2—C31.368 (4)C14—C151.377 (3)
C3—C41.385 (4)O1—H10.8200
C4—C4A1.389 (3)C1—H1A0.9300
C4A—C9A1.390 (3)C2—H20.9300
C4A—C4B1.472 (3)C3—H30.9300
C4B—C51.387 (3)C4—H40.9300
C4B—C8A1.393 (3)C5—H50.9300
C5—C61.377 (4)C6—H60.9300
C6—C71.380 (4)C7—H70.9300
C7—C81.389 (3)C8—H80.9300
C8—C8A1.373 (3)C11—H110.9300
C8A—C91.528 (3)C13—H130.9300
C9—C101.526 (3)C14—H140.9300
C9—C9A1.532 (3)C15—H150.9300
C10—C111.380 (3)C16—H16A0.9600
C10—C151.383 (3)C16—H16B0.9600
C11—C121.392 (3)C16—H16C0.9600
C9A—C1—C2118.4 (3)C15—C14—C13120.4 (3)
C3—C2—C1121.2 (3)C14—C15—C10120.2 (2)
C2—C3—C4121.1 (3)C9—O1—H1109.5
C3—C4—C4A118.1 (3)C9A—C1—H1A120.8
C4—C4A—C9A120.4 (2)C2—C1—H1A120.8
C4—C4A—C4B130.8 (2)C3—C2—H2119.4
C9A—C4A—C4B108.8 (2)C1—C2—H2119.4
C5—C4B—C8A120.1 (2)C2—C3—H3119.5
C5—C4B—C4A131.4 (2)C4—C3—H3119.5
C8A—C4B—C4A108.50 (19)C3—C4—H4120.9
C6—C5—C4B118.8 (2)C4A—C4—H4120.9
C5—C6—C7120.8 (2)C6—C5—H5120.6
C6—C7—C8120.8 (3)C4B—C5—H5120.6
C8A—C8—C7118.4 (2)C5—C6—H6119.6
C8—C8A—C4B121.1 (2)C7—C6—H6119.6
C8—C8A—C9128.0 (2)C6—C7—H7119.6
C4B—C8A—C9110.90 (19)C8—C7—H7119.6
O1—C9—C10107.38 (17)C8A—C8—H8120.8
O1—C9—C8A112.90 (18)C7—C8—H8120.8
C10—C9—C8A110.66 (18)C10—C11—H11119.1
O1—C9—C9A112.62 (18)C12—C11—H11119.1
C10—C9—C9A112.30 (18)C14—C13—H13119.7
C8A—C9—C9A101.00 (17)C12—C13—H13119.7
C1—C9A—C4A120.8 (2)C15—C14—H14119.8
C1—C9A—C9128.5 (2)C13—C14—H14119.8
C4A—C9A—C9110.7 (2)C14—C15—H15119.9
C11—C10—C15118.7 (2)C10—C15—H15119.9
C11—C10—C9121.6 (2)C12—C16—H16A109.5
C15—C10—C9119.7 (2)C12—C16—H16B109.5
C10—C11—C12121.8 (2)H16A—C16—H16B109.5
C13—C12—C11118.2 (2)C12—C16—H16C109.5
C13—C12—C16121.0 (2)H16A—C16—H16C109.5
C11—C12—C16120.7 (2)H16B—C16—H16C109.5
C14—C13—C12120.7 (2)
C9A—C1—C2—C31.2 (4)C2—C1—C9A—C9179.6 (2)
C1—C2—C3—C41.4 (4)C4—C4A—C9A—C11.5 (3)
C2—C3—C4—C4A0.1 (4)C4B—C4A—C9A—C1177.7 (2)
C3—C4—C4A—C9A1.3 (3)C4—C4A—C9A—C9178.3 (2)
C3—C4—C4A—C4B177.6 (2)C4B—C4A—C9A—C92.5 (2)
C4—C4A—C4B—C51.2 (4)O1—C9—C9A—C156.1 (3)
C9A—C4A—C4B—C5177.8 (2)C10—C9—C9A—C165.3 (3)
C4—C4A—C4B—C8A179.4 (2)C8A—C9—C9A—C1176.8 (2)
C9A—C4A—C4B—C8A0.4 (2)O1—C9—C9A—C4A124.1 (2)
C8A—C4B—C5—C60.1 (4)C10—C9—C9A—C4A114.5 (2)
C4A—C4B—C5—C6177.9 (2)C8A—C9—C9A—C4A3.4 (2)
C4B—C5—C6—C70.5 (4)O1—C9—C10—C1111.8 (3)
C5—C6—C7—C80.1 (4)C8A—C9—C10—C11111.8 (2)
C6—C7—C8—C8A0.5 (4)C9A—C9—C10—C11136.1 (2)
C7—C8—C8A—C4B0.9 (3)O1—C9—C10—C15170.8 (2)
C7—C8—C8A—C9179.8 (2)C8A—C9—C10—C1565.6 (3)
C5—C4B—C8A—C80.6 (3)C9A—C9—C10—C1546.4 (3)
C4A—C4B—C8A—C8179.0 (2)C15—C10—C11—C120.6 (4)
C5—C4B—C8A—C9179.7 (2)C9—C10—C11—C12176.8 (2)
C4A—C4B—C8A—C92.0 (2)C10—C11—C12—C130.2 (4)
C8—C8A—C9—O157.3 (3)C10—C11—C12—C16178.3 (2)
C4B—C8A—C9—O1123.7 (2)C11—C12—C13—C140.2 (4)
C8—C8A—C9—C1063.1 (3)C16—C12—C13—C14178.3 (3)
C4B—C8A—C9—C10115.9 (2)C12—C13—C14—C150.6 (4)
C8—C8A—C9—C9A177.8 (2)C13—C14—C15—C101.0 (4)
C4B—C8A—C9—C9A3.2 (2)C11—C10—C15—C141.0 (4)
C2—C1—C9A—C4A0.2 (4)C9—C10—C15—C14176.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···C1i0.822.683.486 (3)167
Symmetry code: (i) x, y, z.
 

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