sp-9-(meta-Methyl­phenyl)-9-fluorenol

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.

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


 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

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Computing details

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

Crystal data

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) Å^3	Prism, colorless
Z = 4	0.42 × 0.34 × 0.21 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0675P)^2 + 0.2168P] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···C1^i	0.82	2.68	3.486 (3)	167

Symmetry code: (i) −x, −y, −z.