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The title compound, C
20H
16O, (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
CCDC reference: 221719
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (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
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
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
C20H16O | F(000) = 576 |
Mr = 272.33 | Dx = 1.227 Mg m−3 |
Monoclinic, P21/c | Melting point = 353–354.5 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71069 Å |
a = 9.1443 (12) Å | Cell parameters from 25 reflections |
b = 19.4498 (14) Å | θ = 16.0–20.0° |
c = 8.6651 (10) Å | µ = 0.07 mm−1 |
β = 106.989 (9)° | T = 296 K |
V = 1473.9 (3) Å3 | Prism, colorless |
Z = 4 | 0.42 × 0.34 × 0.21 mm |
Data collection top
Rigaku AFC-5S diffractometer | Rint = 0.027 |
Radiation source: fine-focus sealed tube | θmax = 25.1°, θmin = 2.1° |
Graphite monochromator | h = −10→10 |
ω scans | k = −23→0 |
2804 measured reflections | l = 0→10 |
2620 independent reflections | 3 standard reflections every 100 reflections |
1500 reflections with I > 2σ(I) | intensity decay: 0.3% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H-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 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.10298 (18) | 0.00523 (8) | 0.2586 (2) | 0.0512 (5) | |
C1 | 0.1807 (3) | 0.09719 (14) | −0.0067 (3) | 0.0554 (7) | |
C2 | 0.1491 (4) | 0.12771 (16) | −0.1570 (3) | 0.0662 (8) | |
C3 | 0.0207 (4) | 0.16684 (15) | −0.2171 (3) | 0.0632 (8) | |
C4 | −0.0837 (3) | 0.17597 (13) | −0.1309 (3) | 0.0545 (7) | |
C4A | −0.0543 (3) | 0.14437 (11) | 0.0189 (3) | 0.0424 (6) | |
C4B | −0.1444 (2) | 0.14244 (11) | 0.1346 (3) | 0.0407 (5) | |
C5 | −0.2856 (3) | 0.17036 (13) | 0.1281 (3) | 0.0523 (7) | |
C6 | −0.3456 (3) | 0.15831 (14) | 0.2540 (4) | 0.0593 (7) | |
C7 | −0.2665 (3) | 0.11959 (14) | 0.3852 (4) | 0.0597 (7) | |
C8 | −0.1246 (3) | 0.09167 (12) | 0.3934 (3) | 0.0497 (6) | |
C8A | −0.0655 (2) | 0.10306 (11) | 0.2670 (3) | 0.0389 (5) | |
C9 | 0.0870 (2) | 0.07817 (11) | 0.2486 (3) | 0.0388 (5) | |
C9A | 0.0781 (3) | 0.10594 (11) | 0.0806 (3) | 0.0420 (6) | |
C10 | 0.2204 (2) | 0.10891 (11) | 0.3800 (3) | 0.0393 (5) | |
C11 | 0.3135 (2) | 0.06873 (13) | 0.5003 (3) | 0.0431 (6) | |
C12 | 0.4306 (3) | 0.09697 (13) | 0.6247 (3) | 0.0472 (6) | |
C13 | 0.4527 (3) | 0.16708 (14) | 0.6255 (3) | 0.0572 (7) | |
C14 | 0.3608 (3) | 0.20789 (14) | 0.5061 (3) | 0.0652 (8) | |
C15 | 0.2459 (3) | 0.17908 (13) | 0.3833 (3) | 0.0562 (7) | |
C16 | 0.5280 (3) | 0.05209 (16) | 0.7574 (3) | 0.0736 (9) | |
H1 | 0.0284 | −0.0128 | 0.1949 | 0.077* | |
H1A | 0.2691 | 0.0714 | 0.0344 | 0.066* | |
H2 | 0.2163 | 0.1215 | −0.2183 | 0.079* | |
H3 | 0.0032 | 0.1877 | −0.3175 | 0.076* | |
H4 | −0.1710 | 0.2025 | −0.1721 | 0.065* | |
H5 | −0.3389 | 0.1968 | 0.0401 | 0.063* | |
H6 | −0.4405 | 0.1765 | 0.2505 | 0.071* | |
H7 | −0.3087 | 0.1121 | 0.4693 | 0.072* | |
H8 | −0.0709 | 0.0659 | 0.4823 | 0.060* | |
H11 | 0.2976 | 0.0215 | 0.4981 | 0.052* | |
H13 | 0.5305 | 0.1870 | 0.7074 | 0.069* | |
H14 | 0.3763 | 0.2552 | 0.5086 | 0.078* | |
H15 | 0.1854 | 0.2069 | 0.3023 | 0.067* | |
H16A | 0.6332 | 0.0559 | 0.7593 | 0.110* | |
H16B | 0.4956 | 0.0051 | 0.7380 | 0.110* | |
H16C | 0.5173 | 0.0667 | 0.8594 | 0.110* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0501 (10) | 0.0365 (9) | 0.0585 (11) | −0.0011 (7) | 0.0027 (8) | −0.0035 (8) |
C1 | 0.0515 (15) | 0.0622 (17) | 0.0556 (16) | −0.0043 (12) | 0.0207 (13) | −0.0106 (14) |
C2 | 0.076 (2) | 0.077 (2) | 0.0561 (18) | −0.0196 (17) | 0.0354 (16) | −0.0135 (15) |
C3 | 0.083 (2) | 0.0684 (19) | 0.0396 (15) | −0.0247 (16) | 0.0208 (15) | −0.0035 (13) |
C4 | 0.0621 (16) | 0.0536 (15) | 0.0414 (15) | −0.0054 (12) | 0.0049 (12) | 0.0038 (12) |
C4A | 0.0438 (13) | 0.0425 (13) | 0.0365 (12) | −0.0049 (10) | 0.0048 (10) | −0.0026 (10) |
C4B | 0.0371 (12) | 0.0439 (13) | 0.0365 (12) | −0.0025 (10) | 0.0034 (10) | −0.0049 (11) |
C5 | 0.0413 (14) | 0.0573 (15) | 0.0523 (16) | 0.0068 (12) | 0.0040 (12) | 0.0013 (13) |
C6 | 0.0428 (14) | 0.0646 (18) | 0.074 (2) | 0.0041 (13) | 0.0226 (14) | −0.0052 (15) |
C7 | 0.0593 (17) | 0.0630 (17) | 0.0639 (18) | −0.0038 (13) | 0.0295 (14) | −0.0022 (14) |
C8 | 0.0516 (15) | 0.0527 (15) | 0.0449 (14) | −0.0019 (12) | 0.0145 (12) | 0.0041 (12) |
C8A | 0.0372 (12) | 0.0397 (12) | 0.0368 (13) | −0.0038 (10) | 0.0062 (10) | −0.0027 (10) |
C9 | 0.0382 (12) | 0.0348 (12) | 0.0408 (13) | 0.0014 (10) | 0.0074 (10) | 0.0002 (10) |
C9A | 0.0415 (13) | 0.0424 (13) | 0.0405 (13) | −0.0062 (10) | 0.0095 (11) | −0.0062 (10) |
C10 | 0.0348 (12) | 0.0412 (13) | 0.0402 (13) | 0.0005 (10) | 0.0080 (10) | −0.0038 (10) |
C11 | 0.0413 (13) | 0.0436 (13) | 0.0437 (13) | 0.0026 (10) | 0.0109 (10) | −0.0032 (11) |
C12 | 0.0376 (13) | 0.0620 (16) | 0.0411 (13) | 0.0067 (11) | 0.0101 (11) | −0.0060 (12) |
C13 | 0.0424 (14) | 0.0662 (18) | 0.0553 (16) | −0.0075 (12) | 0.0023 (12) | −0.0128 (14) |
C14 | 0.0588 (17) | 0.0480 (16) | 0.076 (2) | −0.0108 (13) | −0.0011 (15) | −0.0072 (14) |
C15 | 0.0509 (15) | 0.0435 (14) | 0.0620 (17) | −0.0027 (12) | −0.0025 (13) | 0.0032 (13) |
C16 | 0.0671 (19) | 0.082 (2) | 0.0559 (18) | 0.0171 (16) | −0.0064 (15) | −0.0006 (16) |
Geometric parameters (Å, º) top
O1—C9 | 1.426 (3) | C12—C13 | 1.378 (4) |
C1—C9A | 1.377 (3) | C12—C16 | 1.510 (3) |
C1—C2 | 1.382 (4) | C13—C14 | 1.378 (4) |
C2—C3 | 1.368 (4) | C14—C15 | 1.377 (3) |
C3—C4 | 1.385 (4) | O1—H1 | 0.8200 |
C4—C4A | 1.389 (3) | C1—H1A | 0.9300 |
C4A—C9A | 1.390 (3) | C2—H2 | 0.9300 |
C4A—C4B | 1.472 (3) | C3—H3 | 0.9300 |
C4B—C5 | 1.387 (3) | C4—H4 | 0.9300 |
C4B—C8A | 1.393 (3) | C5—H5 | 0.9300 |
C5—C6 | 1.377 (4) | C6—H6 | 0.9300 |
C6—C7 | 1.380 (4) | C7—H7 | 0.9300 |
C7—C8 | 1.389 (3) | C8—H8 | 0.9300 |
C8—C8A | 1.373 (3) | C11—H11 | 0.9300 |
C8A—C9 | 1.528 (3) | C13—H13 | 0.9300 |
C9—C10 | 1.526 (3) | C14—H14 | 0.9300 |
C9—C9A | 1.532 (3) | C15—H15 | 0.9300 |
C10—C11 | 1.380 (3) | C16—H16A | 0.9600 |
C10—C15 | 1.383 (3) | C16—H16B | 0.9600 |
C11—C12 | 1.392 (3) | C16—H16C | 0.9600 |
| | | |
C9A—C1—C2 | 118.4 (3) | C15—C14—C13 | 120.4 (3) |
C3—C2—C1 | 121.2 (3) | C14—C15—C10 | 120.2 (2) |
C2—C3—C4 | 121.1 (3) | C9—O1—H1 | 109.5 |
C3—C4—C4A | 118.1 (3) | C9A—C1—H1A | 120.8 |
C4—C4A—C9A | 120.4 (2) | C2—C1—H1A | 120.8 |
C4—C4A—C4B | 130.8 (2) | C3—C2—H2 | 119.4 |
C9A—C4A—C4B | 108.8 (2) | C1—C2—H2 | 119.4 |
C5—C4B—C8A | 120.1 (2) | C2—C3—H3 | 119.5 |
C5—C4B—C4A | 131.4 (2) | C4—C3—H3 | 119.5 |
C8A—C4B—C4A | 108.50 (19) | C3—C4—H4 | 120.9 |
C6—C5—C4B | 118.8 (2) | C4A—C4—H4 | 120.9 |
C5—C6—C7 | 120.8 (2) | C6—C5—H5 | 120.6 |
C6—C7—C8 | 120.8 (3) | C4B—C5—H5 | 120.6 |
C8A—C8—C7 | 118.4 (2) | C5—C6—H6 | 119.6 |
C8—C8A—C4B | 121.1 (2) | C7—C6—H6 | 119.6 |
C8—C8A—C9 | 128.0 (2) | C6—C7—H7 | 119.6 |
C4B—C8A—C9 | 110.90 (19) | C8—C7—H7 | 119.6 |
O1—C9—C10 | 107.38 (17) | C8A—C8—H8 | 120.8 |
O1—C9—C8A | 112.90 (18) | C7—C8—H8 | 120.8 |
C10—C9—C8A | 110.66 (18) | C10—C11—H11 | 119.1 |
O1—C9—C9A | 112.62 (18) | C12—C11—H11 | 119.1 |
C10—C9—C9A | 112.30 (18) | C14—C13—H13 | 119.7 |
C8A—C9—C9A | 101.00 (17) | C12—C13—H13 | 119.7 |
C1—C9A—C4A | 120.8 (2) | C15—C14—H14 | 119.8 |
C1—C9A—C9 | 128.5 (2) | C13—C14—H14 | 119.8 |
C4A—C9A—C9 | 110.7 (2) | C14—C15—H15 | 119.9 |
C11—C10—C15 | 118.7 (2) | C10—C15—H15 | 119.9 |
C11—C10—C9 | 121.6 (2) | C12—C16—H16A | 109.5 |
C15—C10—C9 | 119.7 (2) | C12—C16—H16B | 109.5 |
C10—C11—C12 | 121.8 (2) | H16A—C16—H16B | 109.5 |
C13—C12—C11 | 118.2 (2) | C12—C16—H16C | 109.5 |
C13—C12—C16 | 121.0 (2) | H16A—C16—H16C | 109.5 |
C11—C12—C16 | 120.7 (2) | H16B—C16—H16C | 109.5 |
C14—C13—C12 | 120.7 (2) | | |
| | | |
C9A—C1—C2—C3 | 1.2 (4) | C2—C1—C9A—C9 | −179.6 (2) |
C1—C2—C3—C4 | −1.4 (4) | C4—C4A—C9A—C1 | −1.5 (3) |
C2—C3—C4—C4A | 0.1 (4) | C4B—C4A—C9A—C1 | 177.7 (2) |
C3—C4—C4A—C9A | 1.3 (3) | C4—C4A—C9A—C9 | 178.3 (2) |
C3—C4—C4A—C4B | −177.6 (2) | C4B—C4A—C9A—C9 | −2.5 (2) |
C4—C4A—C4B—C5 | 1.2 (4) | O1—C9—C9A—C1 | −56.1 (3) |
C9A—C4A—C4B—C5 | −177.8 (2) | C10—C9—C9A—C1 | 65.3 (3) |
C4—C4A—C4B—C8A | 179.4 (2) | C8A—C9—C9A—C1 | −176.8 (2) |
C9A—C4A—C4B—C8A | 0.4 (2) | O1—C9—C9A—C4A | 124.1 (2) |
C8A—C4B—C5—C6 | −0.1 (4) | C10—C9—C9A—C4A | −114.5 (2) |
C4A—C4B—C5—C6 | 177.9 (2) | C8A—C9—C9A—C4A | 3.4 (2) |
C4B—C5—C6—C7 | 0.5 (4) | O1—C9—C10—C11 | −11.8 (3) |
C5—C6—C7—C8 | −0.1 (4) | C8A—C9—C10—C11 | 111.8 (2) |
C6—C7—C8—C8A | −0.5 (4) | C9A—C9—C10—C11 | −136.1 (2) |
C7—C8—C8A—C4B | 0.9 (3) | O1—C9—C10—C15 | 170.8 (2) |
C7—C8—C8A—C9 | 179.8 (2) | C8A—C9—C10—C15 | −65.6 (3) |
C5—C4B—C8A—C8 | −0.6 (3) | C9A—C9—C10—C15 | 46.4 (3) |
C4A—C4B—C8A—C8 | −179.0 (2) | C15—C10—C11—C12 | 0.6 (4) |
C5—C4B—C8A—C9 | −179.7 (2) | C9—C10—C11—C12 | −176.8 (2) |
C4A—C4B—C8A—C9 | 2.0 (2) | C10—C11—C12—C13 | −0.2 (4) |
C8—C8A—C9—O1 | 57.3 (3) | C10—C11—C12—C16 | 178.3 (2) |
C4B—C8A—C9—O1 | −123.7 (2) | C11—C12—C13—C14 | 0.2 (4) |
C8—C8A—C9—C10 | −63.1 (3) | C16—C12—C13—C14 | −178.3 (3) |
C4B—C8A—C9—C10 | 115.9 (2) | C12—C13—C14—C15 | −0.6 (4) |
C8—C8A—C9—C9A | 177.8 (2) | C13—C14—C15—C10 | 1.0 (4) |
C4B—C8A—C9—C9A | −3.2 (2) | C11—C10—C15—C14 | −1.0 (4) |
C2—C1—C9A—C4A | 0.2 (4) | C9—C10—C15—C14 | 176.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···C1i | 0.82 | 2.68 | 3.486 (3) | 167 |
Symmetry code: (i) −x, −y, −z. |
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