9-(meta-tert-Butyl­phenyl)-9-fluorenol

Meyers, C.Y.; McLean, A.W.; Robinson, P.D.

doi:10.1107/S1600536803011954

9-(meta-tert-Butylphenyl)-9-fluorenol

C. Y. Meyers, A. W. McLean and P. D. Robinson

The title compound, C₂₃H₂₂O, is composed of molecules bonded into linear one-dimensional chains through O—H

π(fluorene) hydrogen bonds, each molecule being both H-atom donor and acceptor. No O—H

O—H hydrogen bonding is exhibited, despite the reasonable donor–acceptor proximity [2.849 (3) Å]. The melted crystals failed to recrystallize on cooling, but solution NMR showed that no decomposition had occurred during the melting.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803011954/lh6066sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803011954/lh6066Isup2.hkl Contains datablock I

CCDC reference: 217464

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R factor = 0.046
wR factor = 0.167
Data-to-parameter ratio = 14.2

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

Comment top

We recently reported the crystal structure of 9-(para-tert-butylphenyl)-9-fluorenol (II) (McLean et al., 2003), and compared it with that of its isomeric 9-(ortho-tert-butylphenyl)-9-fluorenol (III) (Robinson et al., 1998; see also Meyers et al., 1999) whose NMR spectrum shows it to be rotationally restricted at the 9-position in solution. The similarities and differences between isomers (II) and (III) prompted us to study the crystal structure of the third isomer, 9-(meta-tert-butylphenyl)-9-fluorenol (I), which is freely rotating in solution, like (II), but, like (III), could exhibit conformational preferences in its crystalline structure.

The structure of (I) with atom numbering is shown in Fig. 1. No unusual geometric parameters were noted. The angle between the fluorene least-squares plane and that of the phenyl ring is 84.10 (12)°. Although the meta-tert-butylphenyl group of (I) is freely rotating in solution, it crystallizes in an sp conformation like its ortho-tert-butylphenyl isomer (III) in which this conformation is thermodynamically preferred over the ap conformation because of rotational and steric restrictions. Presumably, the favorability of the sp conformation of (I) is associated with its molecular packing. While the para isomer (II) and ortho isomer (III) crystallized in two somewhat different molecular conformations, respectively, crystalline (I) is composed of a single molecular conformation. The latter molecules are linked into linear one-dimensional chains through O—H^···π(fluorene) hydrogen bonds, each molecule being both H-donor and -acceptor. The hydroxyl H atom most closely approaches the fluorene pi-cloud near C2 as depicted in Fig. 2 and the chains propagate in the c-axial direction by simple unit translations. The hydrogen bond geometry is given in Table 1. A view of the molecular packing as viewed down the a axis is shown in Fig. 3 with the previously described molecular chains propagating from right to left. Note that there are two centrosymmetrically related orientations of the chains which form what could be called `layers' of chains parallel to (010); three such layers are apparent in this figure. Another important difference resides in the fact that while (II) as well as (III) exhibit both O—H···O—H and O—H^···π(fluorene) hydrogen bonding, only the latter is apparent in (I). It is pertinent to note in this context that within the `layers' of (I), adjacent hydroxyl groups are quite intimately associated, with an O^···O distance of only 2.849 (3) Å, a respectable donor-acceptor distance. Despite this fact, no O—H^···O hydrogen bonds are formed, because the hydroxyl H atoms are not in reasonable positions to hydrogen bond with the respective O atoms. It is worth noting that the closely associated hydroxyl groups are related by an inversion center and it may be difficult or impossible for O—H···O—H hydrogen bonding to occur under a symmetry constraint of this type.

We have already pointed out that crystalline fluorenols (II) and (III), respectively, have sharp melting points, but their melts fail to recrystallize, even after prolonged standing, although NMR shows that no decomposition had occurred (McLean et al., 2003). Now we find that fluorenol (I) behaves identically. It appears that in the non-packing melt orientation, the molecules of all three of these isomeric 9-(tert-butylphenyl)-9-fluorenols have difficulty reorganizing into the orientation required for their crystalline packing.

Experimental top

Freshly distilled tetrahydrofuran (20 ml) and 1,2-dibromoethane (0.30 ml, 3.48 mmol) were added to a flask containing magnesium (0.29 g, 11.82 mmol) and the mixture was gently heated. When bubbles appeared at the surface of the magnesium, meta-tert-butylbromobenzene (Czarnik, 1984; Schaefer & Higgins, 1967) (1.85 g, 12.09 mmol) was added and the mixture was gently heated until all of the magnesium was consumed. A solution of 9-fluorenone (1.01 g, 5.62 mmol) in tetrahydrofuran (15 ml) was added and the mixture, which immediately became yellow-brown, was refluxed for 22 h. A saturated aqueous NH₄Cl solution was then added, the mixture was extracted with ether and the combined extracts were dried and concentrated in vacuo leaving a dark yellow oil that solidified on standing; 1.41 g, 79.8% yield. Recrystallization (hexanes) afforded colorless crystals of (I), mp 374.5–376 K. The melt did not recrystallize even on standing for several days, although its ¹H NMR spectrum was identical to that of the crystals, showing that they did not decompose on melting. NMR (CDCl₃): ¹H, δ 1.30 (s, 9 H), 2.43 (s, 1 H), 6.92–6.95 (m, 1 H), 7.10–7.38 (m, 8 H), 7.64–7.71 (m, 3 H); ¹³C: δ 31.40, 34.81, 83.94, 120.06, 122.33, 122.75, 124.19, 124.81, 127.77, 128.37, 129.00, 139.66, 142.82, 150.57, 151.15.

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 (Molecular Structure Corporation, 1997) and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2000).

Figures top

	Fig. 1. The molecular structure and atom numbering scheme for (I) with displacement ellipsoids at the 30% probablilty level.
	Fig. 2. The hydrogen bonding scheme in (I) [symmetry codes: (i) x, y, 1 + z; (ii) x, y, 2 + z].
	Fig. 3. The molecular packing in (I) as viewed down the a axis.

9-(meta-tert-Butylphenyl)-9-fluorenol top

Crystal data top

C₂₃H₂₂O	D_x = 1.168 Mg m⁻³
M_r = 314.41	Melting point = 374.5–376 K
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 25 reflections
a = 22.123 (5) Å	θ = 11.2–18.8°
b = 24.203 (3) Å	µ = 0.07 mm⁻¹
c = 6.676 (4) Å	T = 296 K
V = 3575 (2) Å³	Prism, colorless
Z = 8	0.49 × 0.43 × 0.22 mm
F(000) = 1344

Data collection top

Rigaku AFC-5S diffractometer	R_int = 0.0
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 1.8°
Graphite monochromator	h = 0→26
ω scans	k = 0→28
3143 measured reflections	l = 0→7
3143 independent reflections	3 standard reflections every 100 reflections
1395 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0762P)² + 0.4759P] where P = (F_o² + 2F_c²)/3
3143 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₃H₂₂O	V = 3575 (2) Å³
M_r = 314.41	Z = 8
Orthorhombic, Pccn	Mo Kα radiation
a = 22.123 (5) Å	µ = 0.07 mm⁻¹
b = 24.203 (3) Å	T = 296 K
c = 6.676 (4) Å	0.49 × 0.43 × 0.22 mm

Data collection top

Rigaku AFC-5S diffractometer	R_int = 0.0
3143 measured reflections	3 standard reflections every 100 reflections
3143 independent reflections	intensity decay: 0.3%
1395 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 1.00	Δρ_max = 0.24 e Å⁻³
3143 reflections	Δρ_min = −0.18 e Å⁻³
221 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.95676 (9)	0.46596 (7)	0.5989 (3)	0.0535 (6)
C1	0.96983 (17)	0.42586 (14)	0.1468 (5)	0.0717 (10)
C2	0.98627 (19)	0.38514 (17)	0.0105 (6)	0.0859 (12)
C3	0.96488 (19)	0.33206 (18)	0.0313 (7)	0.0905 (13)
C4	0.92542 (17)	0.31832 (14)	0.1853 (6)	0.0788 (11)
C4A	0.90897 (13)	0.35849 (11)	0.3216 (5)	0.0563 (8)
C4B	0.86895 (13)	0.35678 (11)	0.4969 (5)	0.0552 (8)
C5	0.83508 (15)	0.31410 (12)	0.5797 (7)	0.0716 (10)
C6	0.80026 (16)	0.32540 (14)	0.7470 (7)	0.0788 (11)
C7	0.79848 (16)	0.37760 (13)	0.8314 (6)	0.0722 (10)
C8	0.83184 (14)	0.41968 (12)	0.7494 (5)	0.0612 (8)
C8A	0.86704 (13)	0.40894 (11)	0.5836 (5)	0.0494 (7)
C9	0.90797 (13)	0.44872 (10)	0.4691 (4)	0.0458 (7)
C9A	0.93151 (14)	0.41188 (11)	0.3017 (4)	0.0518 (7)
C10	0.87421 (12)	0.49943 (10)	0.3960 (4)	0.0458 (7)
C11	0.88339 (12)	0.55126 (10)	0.4778 (4)	0.0456 (7)
C12	0.85135 (13)	0.59762 (11)	0.4144 (4)	0.0478 (7)
C13	0.80970 (14)	0.59005 (12)	0.2614 (5)	0.0617 (9)
C14	0.79905 (16)	0.53857 (13)	0.1807 (5)	0.0708 (10)
C15	0.83040 (15)	0.49356 (12)	0.2472 (5)	0.0613 (8)
C16	0.86375 (14)	0.65405 (11)	0.5097 (5)	0.0570 (8)
C17	0.92581 (18)	0.67422 (14)	0.4455 (8)	0.1092 (16)
C18	0.86236 (17)	0.64872 (13)	0.7400 (5)	0.0826 (11)
C19	0.81561 (16)	0.69694 (12)	0.4531 (6)	0.0805 (11)
H1	0.9723	0.4387	0.6506	0.080*
H1A	0.9843	0.4617	0.1338	0.086*
H2	1.0119	0.3938	−0.0953	0.103*
H3	0.9770	0.3050	−0.0591	0.109*
H4	0.9103	0.2826	0.1965	0.095*
H5	0.8358	0.2789	0.5241	0.086*
H6	0.7775	0.2972	0.8041	0.095*
H7	0.7747	0.3841	0.9437	0.087*
H8	0.8307	0.4549	0.8049	0.073*
H11	0.9120	0.5553	0.5788	0.055*
H13	0.7885	0.6204	0.2123	0.074*
H14	0.7703	0.5344	0.0802	0.085*
H15	0.8225	0.4589	0.1931	0.074*
H17A	0.9557	0.6472	0.4815	0.164*
H17B	0.9347	0.7085	0.5113	0.164*
H17C	0.9263	0.6796	0.3030	0.164*
H18A	0.8941	0.6244	0.7828	0.124*
H18B	0.8240	0.6340	0.7811	0.124*
H18C	0.8681	0.6845	0.7993	0.124*
H19A	0.8233	0.7308	0.5238	0.121*
H19B	0.7763	0.6832	0.4885	0.121*
H19C	0.8171	0.7037	0.3115	0.121*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0667 (13)	0.0419 (10)	0.0520 (12)	−0.0040 (10)	−0.0148 (11)	0.0052 (10)
C1	0.094 (3)	0.066 (2)	0.054 (2)	0.0183 (19)	−0.003 (2)	0.0011 (17)
C2	0.106 (3)	0.098 (3)	0.054 (2)	0.036 (3)	0.000 (2)	−0.011 (2)
C3	0.098 (3)	0.091 (3)	0.082 (3)	0.035 (2)	−0.022 (3)	−0.042 (2)
C4	0.078 (2)	0.060 (2)	0.099 (3)	0.0145 (19)	−0.021 (3)	−0.029 (2)
C4A	0.0576 (19)	0.0428 (16)	0.068 (2)	0.0110 (14)	−0.0237 (17)	−0.0133 (16)
C4B	0.0526 (17)	0.0431 (16)	0.070 (2)	0.0031 (14)	−0.0190 (18)	0.0004 (15)
C5	0.062 (2)	0.0391 (16)	0.114 (3)	−0.0028 (16)	−0.027 (2)	0.0064 (19)
C6	0.064 (2)	0.063 (2)	0.109 (3)	−0.0098 (18)	−0.013 (2)	0.035 (2)
C7	0.072 (2)	0.070 (2)	0.075 (3)	−0.0061 (19)	0.001 (2)	0.018 (2)
C8	0.078 (2)	0.0545 (18)	0.0515 (19)	−0.0040 (16)	−0.0022 (18)	0.0071 (17)
C8A	0.0574 (17)	0.0373 (15)	0.0534 (19)	−0.0006 (13)	−0.0133 (16)	0.0052 (14)
C9	0.0582 (18)	0.0382 (14)	0.0409 (15)	0.0004 (13)	−0.0093 (15)	−0.0008 (13)
C9A	0.0623 (19)	0.0478 (17)	0.0455 (17)	0.0097 (15)	−0.0078 (16)	−0.0022 (15)
C10	0.0571 (17)	0.0405 (15)	0.0397 (15)	0.0010 (13)	−0.0003 (15)	0.0035 (13)
C11	0.0547 (18)	0.0408 (15)	0.0413 (16)	−0.0013 (12)	−0.0009 (14)	0.0020 (13)
C12	0.0541 (17)	0.0423 (15)	0.0470 (17)	0.0057 (13)	0.0128 (16)	0.0080 (13)
C13	0.080 (2)	0.0497 (18)	0.055 (2)	0.0159 (16)	−0.0043 (19)	0.0079 (16)
C14	0.088 (2)	0.067 (2)	0.057 (2)	0.0147 (19)	−0.0232 (19)	−0.0012 (18)
C15	0.084 (2)	0.0479 (17)	0.0522 (18)	0.0078 (16)	−0.0158 (18)	−0.0075 (15)
C16	0.0608 (19)	0.0391 (16)	0.071 (2)	0.0054 (14)	0.0117 (17)	−0.0029 (15)
C17	0.088 (3)	0.060 (2)	0.180 (5)	−0.018 (2)	0.035 (3)	−0.023 (3)
C18	0.108 (3)	0.063 (2)	0.076 (3)	0.023 (2)	−0.009 (2)	−0.0222 (19)
C19	0.104 (3)	0.0460 (17)	0.092 (3)	0.0207 (18)	0.005 (2)	0.0010 (19)

Geometric parameters (Å, º) top

O1—C9	1.446 (3)	C16—C19	1.535 (4)
C1—C9A	1.379 (4)	C16—C18	1.543 (5)
C1—C2	1.390 (5)	O1—H1	0.8200
C2—C3	1.376 (5)	C1—H1A	0.9300
C3—C4	1.389 (5)	C2—H2	0.9300
C4—C4A	1.380 (4)	C3—H3	0.9300
C4A—C9A	1.391 (4)	C4—H4	0.9300
C4A—C4B	1.468 (4)	C5—H5	0.9300
C4B—C8A	1.389 (4)	C6—H6	0.9300
C4B—C5	1.391 (4)	C7—H7	0.9300
C5—C6	1.384 (5)	C8—H8	0.9300
C6—C7	1.384 (5)	C11—H11	0.9300
C7—C8	1.372 (4)	C13—H13	0.9300
C8—C8A	1.378 (4)	C14—H14	0.9300
C8A—C9	1.526 (4)	C15—H15	0.9300
C9—C10	1.518 (3)	C17—H17A	0.9600
C9—C9A	1.522 (4)	C17—H17B	0.9600
C10—C11	1.383 (3)	C17—H17C	0.9600
C10—C15	1.395 (4)	C18—H18A	0.9600
C11—C12	1.393 (4)	C18—H18B	0.9600
C12—C13	1.388 (4)	C18—H18C	0.9600
C12—C16	1.531 (4)	C19—H19A	0.9600
C13—C14	1.378 (4)	C19—H19B	0.9600
C14—C15	1.365 (4)	C19—H19C	0.9600
C16—C17	1.519 (5)

C9A—C1—C2	118.5 (3)	C9A—C1—H1A	120.7
C3—C2—C1	120.4 (4)	C2—C1—H1A	120.7
C2—C3—C4	120.9 (3)	C3—C2—H2	119.8
C4A—C4—C3	119.0 (3)	C1—C2—H2	119.8
C4—C4A—C9A	119.8 (3)	C2—C3—H3	119.5
C4—C4A—C4B	131.6 (3)	C4—C3—H3	119.5
C9A—C4A—C4B	108.6 (2)	C4A—C4—H4	120.5
C8A—C4B—C5	119.5 (3)	C3—C4—H4	120.5
C8A—C4B—C4A	108.9 (3)	C6—C5—H5	120.9
C5—C4B—C4A	131.5 (3)	C4B—C5—H5	120.9
C6—C5—C4B	118.3 (3)	C5—C6—H6	119.2
C5—C6—C7	121.7 (3)	C7—C6—H6	119.2
C8—C7—C6	120.0 (4)	C8—C7—H7	120.0
C7—C8—C8A	119.0 (3)	C6—C7—H7	120.0
C8—C8A—C4B	121.5 (3)	C7—C8—H8	120.5
C8—C8A—C9	128.2 (3)	C8A—C8—H8	120.5
C4B—C8A—C9	110.3 (3)	C10—C11—H11	118.8
O1—C9—C10	109.1 (2)	C12—C11—H11	118.8
O1—C9—C9A	110.7 (2)	C14—C13—H13	119.3
C10—C9—C9A	114.0 (2)	C12—C13—H13	119.3
O1—C9—C8A	109.0 (2)	C15—C14—H14	119.8
C10—C9—C8A	112.3 (2)	C13—C14—H14	119.8
C9A—C9—C8A	101.6 (2)	C14—C15—H15	119.9
C1—C9A—C4A	121.3 (3)	C10—C15—H15	119.9
C1—C9A—C9	128.1 (3)	C16—C17—H17A	109.5
C4A—C9A—C9	110.6 (3)	C16—C17—H17B	109.5
C11—C10—C15	118.4 (2)	H17A—C17—H17B	109.5
C11—C10—C9	122.3 (2)	C16—C17—H17C	109.5
C15—C10—C9	119.2 (2)	H17A—C17—H17C	109.5
C10—C11—C12	122.4 (3)	H17B—C17—H17C	109.5
C13—C12—C11	117.1 (3)	C16—C18—H18A	109.5
C13—C12—C16	122.9 (2)	C16—C18—H18B	109.5
C11—C12—C16	120.1 (3)	H18A—C18—H18B	109.5
C14—C13—C12	121.4 (3)	C16—C18—H18C	109.5
C15—C14—C13	120.5 (3)	H18A—C18—H18C	109.5
C14—C15—C10	120.2 (3)	H18B—C18—H18C	109.5
C17—C16—C12	109.4 (3)	C16—C19—H19A	109.5
C17—C16—C19	109.9 (3)	C16—C19—H19B	109.5
C12—C16—C19	112.1 (3)	H19A—C19—H19B	109.5
C17—C16—C18	109.0 (3)	C16—C19—H19C	109.5
C12—C16—C18	109.6 (2)	H19A—C19—H19C	109.5
C19—C16—C18	106.7 (3)	H19B—C19—H19C	109.5
C9—O1—H1	109.5

C9A—C1—C2—C3	−0.4 (5)	C4—C4A—C9A—C9	−179.3 (3)
C1—C2—C3—C4	1.5 (6)	C4B—C4A—C9A—C9	1.1 (3)
C2—C3—C4—C4A	−1.6 (5)	O1—C9—C9A—C1	−66.0 (4)
C3—C4—C4A—C9A	0.6 (5)	C10—C9—C9A—C1	57.4 (4)
C3—C4—C4A—C4B	180.0 (3)	C8A—C9—C9A—C1	178.3 (3)
C4—C4A—C4B—C8A	−179.4 (3)	O1—C9—C9A—C4A	113.9 (2)
C9A—C4A—C4B—C8A	0.1 (3)	C10—C9—C9A—C4A	−122.7 (3)
C4—C4A—C4B—C5	−0.2 (5)	C8A—C9—C9A—C4A	−1.8 (3)
C9A—C4A—C4B—C5	179.2 (3)	O1—C9—C10—C11	−11.6 (4)
C8A—C4B—C5—C6	0.1 (5)	C9A—C9—C10—C11	−135.9 (3)
C4A—C4B—C5—C6	−179.0 (3)	C8A—C9—C10—C11	109.3 (3)
C4B—C5—C6—C7	0.2 (5)	O1—C9—C10—C15	171.3 (3)
C5—C6—C7—C8	−0.1 (5)	C9A—C9—C10—C15	47.0 (4)
C6—C7—C8—C8A	−0.3 (5)	C8A—C9—C10—C15	−67.8 (3)
C7—C8—C8A—C4B	0.6 (5)	C15—C10—C11—C12	−1.2 (4)
C7—C8—C8A—C9	−179.4 (3)	C9—C10—C11—C12	−178.3 (2)
C5—C4B—C8A—C8	−0.6 (4)	C10—C11—C12—C13	−0.9 (4)
C4A—C4B—C8A—C8	178.7 (3)	C10—C11—C12—C16	−179.6 (3)
C5—C4B—C8A—C9	179.5 (3)	C11—C12—C13—C14	2.2 (4)
C4A—C4B—C8A—C9	−1.2 (3)	C16—C12—C13—C14	−179.1 (3)
C8—C8A—C9—O1	64.9 (4)	C12—C13—C14—C15	−1.4 (5)
C4B—C8A—C9—O1	−115.1 (2)	C13—C14—C15—C10	−0.9 (5)
C8—C8A—C9—C10	−56.0 (4)	C11—C10—C15—C14	2.1 (5)
C4B—C8A—C9—C10	123.9 (3)	C9—C10—C15—C14	179.3 (3)
C8—C8A—C9—C9A	−178.2 (3)	C13—C12—C16—C17	−108.8 (4)
C4B—C8A—C9—C9A	1.8 (3)	C11—C12—C16—C17	69.9 (4)
C2—C1—C9A—C4A	−0.7 (5)	C13—C12—C16—C19	13.4 (4)
C2—C1—C9A—C9	179.2 (3)	C11—C12—C16—C19	−168.0 (3)
C4—C4A—C9A—C1	0.6 (4)	C13—C12—C16—C18	131.8 (3)
C4B—C4A—C9A—C1	−178.9 (3)	C11—C12—C16—C18	−49.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···C2ⁱ	0.82	2.75	3.436 (5)	143

Symmetry code: (i) x, y, z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₂O
M_r	314.41
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	296
a, b, c (Å)	22.123 (5), 24.203 (3), 6.676 (4)
V (Å³)	3575 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.49 × 0.43 × 0.22

Data collection
Diffractometer	Rigaku AFC-5S diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3143, 3143, 1395
R_int	0.0
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.167, 1.00
No. of reflections	3143
No. of parameters	221
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.18

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,1996), MSC/AFC Diffractometer Control Software, PROCESS in TEXSAN (Molecular Structure Corporation, 1997), SIR92 (Burla et al., 1989), LS in TEXSAN (Molecular Structure Corporation, 1997) and SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2000).