(1R*,2R*,4S*,5R*,6R*,8S*)-4,8-Dimethyl-2,6-diphenyl­bicyclo­[3.3.1]nonane-2,6-diol

Nguyen, V.T.; Bishop, R.; Craig, D.C.; Scudder, M.L.

doi:10.1107/S1600536809009933

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o886

doi:10.1107/S1600536809009933

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(1R,2R,4S,5R,6R,8S)-4,8-Dimethyl-2,6-diphenylbicyclo[3.3.1]nonane-2,6-diol

Vi T. Nguyen,^a Roger Bishop,^a Donald C. Craig ^a and Marcia L. Scudder ^a ^*

^aSchool of Chemistry, University of New South Wales, Sydney 2052, Australia
^*Correspondence e-mail: m.scudder@unsw.edu.au

(Received 23 February 2009; accepted 17 March 2009; online 28 March 2009)

The racemic title compound, C₂₃H₂₈O₂, crystallizes in the space group C2/c as a layered structure in which a centrosymmetric three hydrogen bond sequence links four molecules. Both hydroxy groups are involved in this arrangement, but they differ in that one participates in two hydrogen bonds while the other takes part in only one. Between layers, the aromatic rings take part in edge-face interactions [shortest C—H⋯C distances 3.04, 3.10 and 3.12 Å and angle between normal to planes 86.7(2)°], forming a centrosymmetric dimer. The lattice is further stabilized by C—H⋯π interactions involving both methyl (shortest C⋯C 3.82 and 3.97 Å) and methylene (shortest C⋯C 3.60 Å) groups.

Related literature

Phenylation of endo-4, endo-8-dimethylbicyclo[3.3.1]nonane-2,6- dione (Kim et al., 2002 ) occurs selectively on the exo-faces of the V-shaped molecule to yield the title compound. The related 2,6-dimethyl- substituted compound (Nguyen et al., 2001b ) crystallizes with a hydrogen-bonded ladder structure (Nguyen et al., 2001a ) that is very different to the pattern reported here.

Experimental

Crystal data

C₂₃H₂₈O₂
M_r = 336.5
Monoclinic, C 2/c
a = 18.462 (4) Å
b = 13.310 (1) Å
c = 14.824 (3) Å
β = 92.92 (1)°
V = 3638 (1) Å³
Z = 8
Cu Kα radiation
μ = 0.59 mm⁻¹
T = 294 K
0.30 × 0.15 × 0.12 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
3585 measured reflections
3442 independent reflections
2292 reflections with I > 2σ(I)
R_int = 0.034
1 standard reflections frequency: 30 min intensity decay: 4%

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.062
S = 1.59
3442 reflections
160 parameters
H-atom parameters not refined
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O1ⁱ	1.00	1.97	2.943 (2)	163
O1—H1′O1⋯O2ⁱⁱ	1.00	2.04	2.935 (2)	148
O2—H1O2⋯O1ⁱⁱⁱ	1.00	1.95	2.935 (2)	169
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CAD-4 Manual (Schagen et al., 1989 ); cell refinement: CAD-4 Manual; data reduction: local program; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: RAELS (Rae, 2000 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and CrystalMaker (CrystalMaker, 2005 ); software used to prepare material for publication: local programs.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009933/kp2208sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009933/kp2208Isup2.hkl

checkCIF report

Comment top

Molecules (Fig. 1) are linked by a centrosymmetric triplet of hydrogen bonds utilizing one hydroxy group from each of four molecules (Table 1). The other hydroxy group of each of these molecules participates in an identical hydogen bonding unit, leading to a layer structure in the bc plane (Fig. 2). The hydrogen bonding in this compound is somewhat unusual in that hydroxy group, O1, participates in two hydrogen bonds, whereas O2 only participates in one. The majority of the alicyclic diols studied by us (Kim et al., 2002) have one donor and one acceptor hydrogen bond for each hydroxy group.

The pendant phenyl rings do not participate in the common aromatic offset face-to-face interaction in the crystal structure. Instead, one phenyl ring (C10→C15) is the acceptor of two C_methyl—H···π interactions, one to each surface of the ring (C16—H···π, C23—H···π with shortest H···C distances of 3.97 and 3.82 Å, respectively). The second phenyl ring (C17→C22) takes part in a C_methylene—H···π interaction on one surface (C3—H···π with a shortest H···C distance of 3.60 Å). Its second surface is the acceptor of an edge-to-face interaction utilizing the edge of the C10→C15 ring and creating a centrosymmetric dimer between layers (Fig. 3).

Related literature top

Phenylation of endo-4, endo-8-dimethylbicyclo[3.3.1]nonane-2,6- dione (Kim et al., 2002) occurs selectively on the exo-faces of the V-shaped molecule to yield the title compound. The related 2,6-dimethyl- substituted compound (Nguyen et al., 2001b) crystallizes with a hydrogen-bonded ladder structure (Nguyen et al., 2001a) that is very different to the pattern reported here.

Experimental top

A solution of racemic endo-4,endo-8-dimethylbicyclo[3.3.1]nonane-2,6-dione (Kim et al., 2002) (0.79 g, 4.4 mmol) in dry tetrahydrofuran (30 ml) was added dropwise to a stirred solution of excess phenylmagnesium bromide in dry diethyl ether (10 ml) at -10°C. After 12 h at rt, the reaction was subjected to a standard Grignard reaction work-up to yield the title compound (0.67 g, 47%), m.p. 438-440 K (from acetonitrile). Found: C 82.15, H 8.34; C₂₃H₂₈O₂ requires C 82.10, H 8.39%. ¹³C NMR (75.5 MHz, CDCl₃) δ: 22.0 (CH₃), 32.5 (CH₂), 36.2 (CH), 42.4 (CH), 42.6 (CH₂), 78.4 (C), 125.5 (CH), 127.0 (CH), 128.2 (CH), 148.3 (C). ¹H NMR (300 MHz, CDCl₃) δ: 1.18 (t, J=3.0 Hz, 2H), 1.46 (d, J=6.4 Hz, 6H), 1.57 (bs, 2H, exchanged with D₂O), 2.18–2.39 (m, 6H), 2.44–2.47 (m, 2H), 7.22–7.27 (m, 2H), 7.31–7.36 (m, 4H), 7.52–7.55 (m, 4H). X-ray quality crystals were obtained from tetrahydrofuran solution.

Computing details top

Data collection: CAD-4 Manual (Schagen et al., 1989); cell refinement: CAD-4 Manual (Schagen et al., 1989); data reduction: local program; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: RAELS (Rae, 2000); molecular graphics: ORTEP-3 (Farrugia, 1997) and CrystalMaker (CrystalMaker, 2005); software used to prepare material for publication: local programs.

Figures top

	Fig. 1. Molecular structure of the compound, with ellipsoids drawn at 50% probability level. Only one of the two disordered hydrogen positions is shown for each hydroxy group.
	Fig. 2. A hydrogen bonded layer in the bc plane. Hydrogen bonds are shown by red lines. In Figs. 2 and 3 C is green, O is red.
	Fig. 3. The centrosymmetric dimer links layers by a double edge-face interactions (shown as black arrows).

(1R*,2R*,4S*,5R*,6R*,8S*)- 4,8-Dimethyl-2,6-diphenylbicyclo[3.3.1]nonane-2,6-diol top

Crystal data top

C₂₃H₂₈O₂	F(000) = 1456.0
M_r = 336.5	D_x = 1.23 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
a = 18.462 (4) Å	Cell parameters from 10 reflections
b = 13.310 (1) Å	θ = 20–23°
c = 14.824 (3) Å	µ = 0.59 mm⁻¹
β = 92.92 (1)°	T = 294 K
V = 3638 (1) Å³	Prism, colourless
Z = 8	0.30 × 0.15 × 0.12 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	θ_max = 70°
ω–2θ scans	h = −22→22
3585 measured reflections	k = 0→16
3442 independent reflections	l = −18→0
2292 reflections with I > 2σ(I)	1 standard reflections every 30 min
R_int = 0.034	intensity decay: 4%

Refinement top

Refinement on F	0 restraints
R[F² > 2σ(F²)] = 0.045	H-atom parameters not refined
wR(F²) = 0.062	w = 1/[σ²(F) + 0.0004F²]
S = 1.59	(Δ/σ)_max = 0.004
3442 reflections	Δρ_max = 0.31 e Å⁻³
160 parameters	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₂₃H₂₈O₂	V = 3638 (1) Å³
M_r = 336.5	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 18.462 (4) Å	µ = 0.59 mm⁻¹
b = 13.310 (1) Å	T = 294 K
c = 14.824 (3) Å	0.30 × 0.15 × 0.12 mm
β = 92.92 (1)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.034
3585 measured reflections	1 standard reflections every 30 min
3442 independent reflections	intensity decay: 4%
2292 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.062	H-atom parameters not refined
S = 1.59	Δρ_max = 0.31 e Å⁻³
3442 reflections	Δρ_min = −0.34 e Å⁻³
160 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.27017 (6)	0.26370 (9)	0.09652 (8)	0.0465 (3)
O2	0.30304 (7)	0.58902 (10)	0.32886 (8)	0.0550 (4)
C1	0.32906 (9)	0.42870 (12)	0.08333 (11)	0.0350 (4)
C2	0.33263 (9)	0.32328 (12)	0.12682 (11)	0.0372 (4)
C3	0.3302 (1)	0.3328 (1)	0.2293 (1)	0.0435 (4)
C4	0.3858 (1)	0.4068 (1)	0.2711 (1)	0.0469 (5)
C5	0.38388 (9)	0.51069 (14)	0.22386 (11)	0.0409 (4)
C6	0.31736 (9)	0.58053 (13)	0.23431 (11)	0.0406 (4)
C7	0.24945 (9)	0.53770 (13)	0.18446 (12)	0.0426 (4)
C8	0.25972 (9)	0.49329 (13)	0.09061 (12)	0.0405 (4)
C9	0.39285 (9)	0.49236 (13)	0.12283 (12)	0.0400 (4)
C10	0.39953 (8)	0.26407 (10)	0.09682 (8)	0.0401 (4)
C11	0.42900 (8)	0.28028 (12)	0.01427 (10)	0.0643 (4)
C12	0.48531 (8)	0.22117 (14)	−0.01466 (10)	0.0737 (6)
C13	0.51343 (9)	0.14468 (12)	0.03804 (10)	0.0615 (6)
C14	0.48475 (9)	0.12773 (11)	0.12005 (12)	0.0781 (6)
C15	0.42844 (8)	0.18666 (12)	0.14924 (10)	0.0664 (5)
C16	0.3837 (1)	0.4072 (2)	0.3743 (1)	0.0667 (6)
C17	0.33675 (7)	0.68703 (11)	0.20411 (8)	0.0424 (4)
C18	0.30590 (7)	0.73420 (11)	0.12855 (9)	0.0548 (5)
C19	0.32341 (9)	0.83264 (11)	0.10750 (10)	0.0642 (6)
C20	0.37202 (8)	0.88615 (12)	0.16127 (10)	0.0625 (6)
C21	0.40304 (8)	0.84036 (11)	0.23640 (11)	0.0647 (5)
C22	0.38568 (8)	0.74193 (11)	0.25771 (9)	0.0542 (5)
C23	0.1887 (1)	0.4463 (2)	0.0533 (1)	0.0565 (5)
H1O1	0.2639	0.2649	0.0291	0.047	0.5
H1'O1	0.2614	0.2068	0.1386	0.047	0.5
H1O2	0.2833	0.6535	0.3521	0.055	0.5
H1'O2	0.2723	0.5320	0.3486	0.055	0.5
HC1	0.3367	0.4197	0.0175	0.035
H1C3	0.3397	0.2651	0.2566	0.043
H2C3	0.2807	0.3560	0.2440	0.043
HC4	0.4341	0.3777	0.2583	0.047
HC5	0.4277	0.5486	0.2473	0.041
H1C7	0.2131	0.5932	0.1775	0.043
H2C7	0.2299	0.4834	0.2230	0.043
HC8	0.2674	0.5528	0.0510	0.041
H1C9	0.3937	0.5583	0.0906	0.040
H2C9	0.4394	0.4559	0.1146	0.040
HC11	0.4094	0.3357	−0.0255	0.106
HC12	0.5056	0.2347	−0.0748	0.121
HC13	0.5540	0.1022	0.0171	0.074
HC14	0.5046	0.0722	0.1594	0.130
HC15	0.4084	0.1728	0.2094	0.108
H1C16	0.4204	0.4560	0.4001	0.067
H2C16	0.3343	0.4276	0.3921	0.067
H3C16	0.3951	0.3384	0.3981	0.067
HC18	0.2702	0.6967	0.0882	0.071
HC19	0.3002	0.8649	0.0524	0.086
HC20	0.3846	0.9570	0.1460	0.074
HC21	0.4387	0.8783	0.2765	0.088
HC22	0.4091	0.7102	0.3130	0.069
H1C23	0.1959	0.4176	−0.0079	0.056
H2C23	0.1737	0.3917	0.0948	0.056
H3C23	0.1501	0.4990	0.0486	0.056

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0467 (7)	0.0394 (7)	0.0538 (8)	−0.0053 (6)	0.0064 (6)	0.0009 (6)
O2	0.079 (1)	0.0515 (8)	0.0364 (7)	0.0074 (7)	0.0167 (6)	−0.0026 (6)
C1	0.0390 (9)	0.0344 (9)	0.0321 (9)	0.0031 (7)	0.0066 (7)	0.0017 (7)
C2	0.0421 (9)	0.0350 (9)	0.0347 (9)	0.0021 (7)	0.0049 (7)	0.0004 (7)
C3	0.056 (1)	0.040 (1)	0.0345 (9)	0.0080 (8)	0.0085 (8)	0.0048 (8)
C4	0.057 (1)	0.047 (1)	0.036 (1)	0.0145 (9)	−0.0012 (8)	−0.0018 (8)
C5	0.0410 (9)	0.043 (1)	0.039 (1)	0.0035 (8)	0.0019 (7)	−0.0040 (8)
C6	0.047 (1)	0.041 (1)	0.0351 (9)	0.0058 (8)	0.0078 (7)	−0.0021 (8)
C7	0.041 (1)	0.0391 (9)	0.049 (1)	0.0048 (8)	0.0104 (8)	−0.0010 (8)
C8	0.042 (1)	0.0359 (9)	0.044 (1)	0.0035 (8)	0.0024 (7)	0.0029 (8)
C9	0.0383 (9)	0.041 (1)	0.041 (1)	0.0027 (8)	0.0072 (7)	−0.0030 (8)
C10	0.0461 (6)	0.0363 (7)	0.0374 (6)	0.0049 (5)	−0.0017 (5)	−0.0050 (5)
C11	0.0687 (7)	0.0782 (9)	0.0472 (7)	0.0294 (7)	0.0144 (6)	0.0092 (5)
C12	0.0726 (8)	0.096 (1)	0.0541 (8)	0.0348 (8)	0.0148 (7)	−0.0006 (7)
C13	0.0570 (7)	0.0582 (9)	0.069 (1)	0.0159 (7)	0.0054 (6)	−0.0150 (7)
C14	0.0783 (9)	0.0679 (9)	0.090 (1)	0.0373 (8)	0.0233 (8)	0.0189 (7)
C15	0.0716 (7)	0.0639 (8)	0.0652 (7)	0.0319 (6)	0.0168 (6)	0.0192 (6)
C16	0.097 (2)	0.066 (2)	0.036 (1)	0.022 (1)	−0.010 (1)	0.002 (1)
C17	0.0439 (7)	0.0426 (5)	0.0411 (7)	0.0037 (5)	0.0076 (5)	−0.0070 (4)
C18	0.0647 (8)	0.0496 (5)	0.0497 (7)	0.0024 (5)	0.0012 (5)	0.0020 (5)
C19	0.078 (1)	0.0509 (6)	0.0642 (8)	0.0039 (5)	0.0095 (6)	0.0075 (6)
C20	0.070 (1)	0.0448 (5)	0.074 (1)	0.0009 (5)	0.0224 (8)	−0.0018 (5)
C21	0.070 (1)	0.0486 (5)	0.075 (1)	−0.0098 (6)	0.0067 (7)	−0.0079 (5)
C22	0.0575 (8)	0.0477 (5)	0.0571 (7)	−0.0055 (5)	0.0001 (5)	−0.0075 (5)
C23	0.046 (1)	0.048 (1)	0.074 (2)	0.0075 (9)	−0.010 (1)	−0.004 (1)

Geometric parameters (Å, º) top

O1—C2	1.452 (2)	C9—H2C9	1.000
O1—H1O1	1.000	C10—C11	1.381 (1)
O1—H1'O1	1.000	C10—C15	1.381 (1)
O2—C6	1.444 (2)	C11—C12	1.389 (1)
O2—H1O2	1.000	C11—HC11	1.000
O2—H1'O2	1.000	C12—C13	1.369 (1)
C1—C2	1.544 (2)	C12—HC12	1.000
C1—C8	1.550 (2)	C13—C14	1.369 (1)
C1—C9	1.542 (2)	C13—HC13	1.000
C1—HC1	1.000	C14—C15	1.389 (1)
C2—C3	1.527 (2)	C14—HC14	1.000
C2—C10	1.549 (2)	C15—HC15	1.000
C3—C4	1.531 (3)	C16—H1C16	1.000
C3—H1C3	1.000	C16—H2C16	1.000
C3—H2C3	1.000	C16—H3C16	1.000
C4—C5	1.550 (2)	C17—C18	1.381 (1)
C4—C16	1.532 (3)	C17—C22	1.381 (1)
C4—HC4	1.000	C18—C19	1.389 (1)
C5—C6	1.554 (2)	C18—HC18	1.000
C5—C9	1.535 (2)	C19—C20	1.369 (1)
C5—HC5	1.000	C19—HC19	1.000
C6—C7	1.532 (2)	C20—C21	1.369 (1)
C6—C17	1.534 (2)	C20—HC20	1.000
C7—C8	1.532 (2)	C21—C22	1.389 (1)
C7—H1C7	1.000	C21—HC21	1.000
C7—H2C7	1.000	C22—HC22	1.000
C8—C23	1.530 (2)	C23—H1C23	1.000
C8—HC8	1.000	C23—H2C23	1.000
C9—H1C9	1.000	C23—H3C23	1.000

C2—O1—H1O1	110.4	C1—C9—C5	109.8 (1)
C2—O1—H1'O1	111.8	C1—C9—H1C9	109.4
H1O1—O1—H1'O1	128.5	C1—C9—H2C9	109.4
C6—O2—H1O2	119.3	C5—C9—H1C9	109.4
C6—O2—H1'O2	111.1	C5—C9—H2C9	109.4
H1O2—O2—H1'O2	109.2	H1C9—C9—H2C9	109.5
C2—C1—C8	119.5 (1)	C2—C10—C11	122.0 (1)
C2—C1—C9	109.0 (1)	C2—C10—C15	120.6 (1)
C2—C1—HC1	107.0	C11—C10—C15	117.2 (1)
C8—C1—C9	106.6 (1)	C10—C11—C12	121.3 (1)
C8—C1—HC1	107.0	C10—C11—HC11	119.3
C9—C1—HC1	107.0	C12—C11—HC11	119.3
O1—C2—C1	110.6 (1)	C11—C12—C13	120.9 (1)
O1—C2—C3	106.9 (1)	C11—C12—HC12	119.6
O1—C2—C10	105.4 (1)	C13—C12—HC12	119.6
C1—C2—C3	109.7 (1)	C12—C13—C14	118.5 (1)
C1—C2—C10	111.1 (1)	C12—C13—HC13	120.8
C3—C2—C10	113.1 (1)	C14—C13—HC13	120.8
C2—C3—C4	113.8 (2)	C13—C14—C15	120.9 (1)
C2—C3—H1C3	108.4	C13—C14—HC14	119.6
C2—C3—H2C3	108.4	C15—C14—HC14	119.6
C4—C3—H1C3	108.4	C10—C15—C14	121.3 (1)
C4—C3—H2C3	108.4	C10—C15—HC15	119.3
H1C3—C3—H2C3	109.5	C14—C15—HC15	119.3
C3—C4—C5	113.0 (1)	C4—C16—H1C16	109.5
C3—C4—C16	110.9 (2)	C4—C16—H2C16	109.5
C3—C4—HC4	105.1	C4—C16—H3C16	109.5
C5—C4—C16	116.5 (2)	H1C16—C16—H2C16	109.5
C5—C4—HC4	105.1	H1C16—C16—H3C16	109.5
C16—C4—HC4	105.1	H2C16—C16—H3C16	109.5
C4—C5—C6	119.3 (2)	C6—C17—C18	124.3 (1)
C4—C5—C9	107.4 (1)	C6—C17—C22	118.4 (1)
C4—C5—HC5	107.1	C18—C17—C22	117.2 (1)
C6—C5—C9	108.5 (1)	C17—C18—C19	121.3 (1)
C6—C5—HC5	107.1	C17—C18—HC18	119.3
C9—C5—HC5	107.1	C19—C18—HC18	119.3
O2—C6—C5	109.2 (1)	C18—C19—C20	120.9 (1)
O2—C6—C7	108.1 (1)	C18—C19—HC19	119.6
O2—C6—C17	105.5 (1)	C20—C19—HC19	119.6
C5—C6—C7	111.1 (1)	C19—C20—C21	118.5 (1)
C5—C6—C17	109.0 (1)	C19—C20—HC20	120.8
C7—C6—C17	113.6 (1)	C21—C20—HC20	120.8
C6—C7—C8	116.4 (1)	C20—C21—C22	120.9 (1)
C6—C7—H1C7	107.7	C20—C21—HC21	119.6
C6—C7—H2C7	107.7	C22—C21—HC21	119.6
C8—C7—H1C7	107.7	C17—C22—C21	121.3 (1)
C8—C7—H2C7	107.7	C17—C22—HC22	119.3
H1C7—C7—H2C7	109.5	C21—C22—HC22	119.3
C1—C8—C7	114.7 (1)	C8—C23—H1C23	109.5
C1—C8—C23	116.3 (1)	C8—C23—H2C23	109.5
C1—C8—HC8	104.8	C8—C23—H3C23	109.5
C7—C8—C23	110.0 (2)	H1C23—C23—H2C23	109.5
C7—C8—HC8	104.8	H1C23—C23—H3C23	109.5
C23—C8—HC8	104.8	H2C23—C23—H3C23	109.5

H1O1—O1—C2—C1	50.8	C4—C5—C9—C1	62.1 (2)
H1O1—O1—C2—C3	170.1	C4—C5—C9—H1C9	−177.9
H1O1—O1—C2—C10	−69.4	C4—C5—C9—H2C9	−58.0
H1'O1—O1—C2—C1	−159.4	C6—C5—C9—C1	−68.1 (2)
H1'O1—O1—C2—C3	−40.1	C6—C5—C9—H1C9	52.0
H1'O1—O1—C2—C10	80.5	C6—C5—C9—H2C9	171.9
H1O2—O2—C6—C5	146.9	HC5—C5—C9—C1	176.7
H1O2—O2—C6—C7	−92.1	HC5—C5—C9—H1C9	−63.2
H1O2—O2—C6—C17	29.8	HC5—C5—C9—H2C9	56.7
H1'O2—O2—C6—C5	−84.8	O2—C6—C7—C8	−162.2 (1)
H1'O2—O2—C6—C7	36.2	O2—C6—C7—H1C7	76.8
H1'O2—O2—C6—C17	158.1	O2—C6—C7—H2C7	−41.2
C8—C1—C2—O1	52.7 (2)	C5—C6—C7—C8	−42.4 (2)
C8—C1—C2—C3	−64.9 (2)	C5—C6—C7—H1C7	−163.4
C8—C1—C2—C10	169.3 (1)	C5—C6—C7—H2C7	78.6
C9—C1—C2—O1	175.5 (1)	C17—C6—C7—C8	81.0 (2)
C9—C1—C2—C3	57.9 (2)	C17—C6—C7—H1C7	−40.0
C9—C1—C2—C10	−67.8 (2)	C17—C6—C7—H2C7	−158.0
HC1—C1—C2—O1	−69.0	O2—C6—C17—C18	−130.1 (1)
HC1—C1—C2—C3	173.4	O2—C6—C17—C22	46.7 (1)
HC1—C1—C2—C10	47.6	C5—C6—C17—C18	112.8 (1)
C2—C1—C8—C7	73.1 (2)	C5—C6—C17—C22	−70.4 (1)
C2—C1—C8—C23	−57.3 (2)	C7—C6—C17—C18	−11.8 (2)
C2—C1—C8—HC8	−172.5	C7—C6—C17—C22	165.0 (1)
C9—C1—C8—C7	−50.9 (2)	C6—C7—C8—C1	42.0 (2)
C9—C1—C8—C23	178.7 (1)	C6—C7—C8—C23	175.4 (1)
C9—C1—C8—HC8	63.5	C6—C7—C8—HC8	−72.4
HC1—C1—C8—C7	−165.2	H1C7—C7—C8—C1	163.0
HC1—C1—C8—C23	64.4	H1C7—C7—C8—C23	−63.6
HC1—C1—C8—HC8	−50.8	H1C7—C7—C8—HC8	48.6
C2—C1—C9—C5	−65.5 (2)	H2C7—C7—C8—C1	−79.0
C2—C1—C9—H1C9	174.5	H2C7—C7—C8—C23	54.4
C2—C1—C9—H2C9	54.6	H2C7—C7—C8—HC8	166.6
C8—C1—C9—C5	64.8 (2)	C1—C8—C23—H1C23	−47.4
C8—C1—C9—H1C9	−55.3	C1—C8—C23—H2C23	72.6
C8—C1—C9—H2C9	−175.1	C1—C8—C23—H3C23	−167.4
HC1—C1—C9—C5	179.1	C7—C8—C23—H1C23	−180.0
HC1—C1—C9—H1C9	59.0	C7—C8—C23—H2C23	−60.0
HC1—C1—C9—H2C9	−60.9	C7—C8—C23—H3C23	60.0
O1—C2—C3—C4	−171.2 (1)	HC8—C8—C23—H1C23	67.8
O1—C2—C3—H1C3	68.1	HC8—C8—C23—H2C23	−172.2
O1—C2—C3—H2C3	−50.6	HC8—C8—C23—H3C23	−52.2
C1—C2—C3—C4	−51.4 (2)	C2—C10—C11—C12	−174.8 (1)
C1—C2—C3—H1C3	−172.0	C2—C10—C11—HC11	5.2
C1—C2—C3—H2C3	69.3	C15—C10—C11—C12	0.0 (1)
C10—C2—C3—C4	73.3 (2)	C15—C10—C11—HC11	180.0
C10—C2—C3—H1C3	−47.4	C2—C10—C15—C14	174.9 (1)
C10—C2—C3—H2C3	−166.1	C2—C10—C15—HC15	−5.1
O1—C2—C10—C11	90.9 (1)	C11—C10—C15—C14	0.0 (1)
O1—C2—C10—C15	−83.7 (1)	C11—C10—C15—HC15	180.0
C1—C2—C10—C11	−28.9 (2)	C10—C11—C12—C13	0.0 (1)
C1—C2—C10—C15	156.5 (1)	C10—C11—C12—HC12	−180.0
C3—C2—C10—C11	−152.7 (1)	HC11—C11—C12—C13	180.0
C3—C2—C10—C15	32.6 (2)	HC11—C11—C12—HC12	0.0
C2—C3—C4—C5	50.8 (2)	C11—C12—C13—C14	0.0 (1)
C2—C3—C4—C16	−176.2 (2)	C11—C12—C13—HC13	180.0
C2—C3—C4—HC4	−63.2	HC12—C12—C13—C14	180.0
H1C3—C3—C4—C5	171.4	HC12—C12—C13—HC13	0.0
H1C3—C3—C4—C16	−55.6	C12—C13—C14—C15	0.0 (1)
H1C3—C3—C4—HC4	57.4	C12—C13—C14—HC14	180.0
H2C3—C3—C4—C5	−69.9	HC13—C13—C14—C15	−180.0
H2C3—C3—C4—C16	63.1	HC13—C13—C14—HC14	0.0
H2C3—C3—C4—HC4	176.1	C13—C14—C15—C10	0.0 (1)
C3—C4—C5—C6	69.4 (2)	C13—C14—C15—HC15	−180.0
C3—C4—C5—C9	−54.4 (2)	HC14—C14—C15—C10	180.0
C3—C4—C5—HC5	−169.1	HC14—C14—C15—HC15	0.0
C16—C4—C5—C6	−60.9 (2)	C6—C17—C18—C19	176.8 (1)
C16—C4—C5—C9	175.3 (2)	C6—C17—C18—HC18	−3.2
C16—C4—C5—HC5	60.7	C22—C17—C18—C19	0.0 (1)
HC4—C4—C5—C6	−176.6	C22—C17—C18—HC18	180.0
HC4—C4—C5—C9	59.6	C6—C17—C22—C21	−177.0 (1)
HC4—C4—C5—HC5	−55.1	C6—C17—C22—HC22	3.0
C3—C4—C16—H1C16	180.0	C18—C17—C22—C21	0.0 (1)
C3—C4—C16—H2C16	−60.0	C18—C17—C22—HC22	180.0
C3—C4—C16—H3C16	60.0	C17—C18—C19—C20	0.0 (1)
C5—C4—C16—H1C16	−48.8	C17—C18—C19—HC19	180.0
C5—C4—C16—H2C16	71.2	HC18—C18—C19—C20	−180.0
C5—C4—C16—H3C16	−168.8	HC18—C18—C19—HC19	0.0
HC4—C4—C16—H1C16	67.0	C18—C19—C20—C21	0.0 (1)
HC4—C4—C16—H2C16	−173.0	C18—C19—C20—HC20	−180.0
HC4—C4—C16—H3C16	−53.0	HC19—C19—C20—C21	180.0
C4—C5—C6—O2	50.1 (2)	HC19—C19—C20—HC20	0.0
C4—C5—C6—C7	−69.1 (2)	C19—C20—C21—C22	0.0 (1)
C4—C5—C6—C17	165.0 (1)	C19—C20—C21—HC21	−180.0
C9—C5—C6—O2	173.4 (1)	HC20—C20—C21—C22	−180.0
C9—C5—C6—C7	54.2 (2)	HC20—C20—C21—HC21	0.0
C9—C5—C6—C17	−71.8 (2)	C20—C21—C22—C17	0.0 (1)
HC5—C5—C6—O2	−71.4	C20—C21—C22—HC22	180.0
HC5—C5—C6—C7	169.4	HC21—C21—C22—C17	180.0
HC5—C5—C6—C17	43.4	HC21—C21—C22—HC22	0.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O1ⁱ	1.00	1.97	2.943 (2)	163
O1—H1′O1···O2ⁱⁱ	1.00	2.04	2.935 (2)	148
O2—H1O2···O1ⁱⁱⁱ	1.00	1.95	2.935 (2)	169

Symmetry codes: (i) −x+1/2, −y+1/2, −z; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₈O₂
M_r	336.5
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	294
a, b, c (Å)	18.462 (4), 13.310 (1), 14.824 (3)
β (°)	92.92 (1)
V (Å³)	3638 (1)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.30 × 0.15 × 0.12

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3585, 3442, 2292
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.062, 1.59
No. of reflections	3442
No. of parameters	160
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.34

Computer programs: CAD-4 Manual (Schagen et al., 1989), SIR92 (Altomare et al., 1994), RAELS (Rae, 2000), ORTEP-3 (Farrugia, 1997) and CrystalMaker (CrystalMaker, 2005), local programs.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O1ⁱ	1.00	1.97	2.943 (2)	163
O1—H1'O1···O2ⁱⁱ	1.00	2.04	2.935 (2)	148
O2—H1O2···O1ⁱⁱⁱ	1.00	1.95	2.935 (2)	169

Symmetry codes: (i) −x+1/2, −y+1/2, −z; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+1/2, y+1/2, −z+1/2.

Acknowledgements

This research was supported by the Australian Research Council.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
CrystalMaker (2005). CrystalMaker. CrystalMaker Software Limited, Yarnton England. URL: www.CrystalMaker.co.uk. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Kim, S., Bishop, R., Craig, D. C., Dance, I. G. & Scudder, M. L. (2002). J. Org. Chem. 67, 3221–3230. Web of Science CSD CrossRef PubMed CAS Google Scholar
Nguyen, V. T., Ahn, P. D., Bishop, R., Scudder, M. L. & Craig, D. C. (2001a). Eur. J. Org. Chem. pp. 4489–4499. CrossRef Google Scholar
Nguyen, V. T., Bishop, R., Craig, D. C. & Scudder, M. L. (2001b). Supramol. Chem. 13, 103–107. Web of Science CrossRef CAS Google Scholar
Rae, A. D. (2000). RAELS. Australian National University, Canberra, Australia. Google Scholar
Schagen, J. D., Straver, L., van Meurs, F. & Williams, G. (1989). CAD-4 Manual. Enraf–Nonius, Delft, The Netherlands. Google Scholar

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Volume 65| Part 4| April 2009| Page o886

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(1R*,2R*,4S*,5R*,6R*,8S*)-4,8-Di­methyl-2,6-di­phenyl­bi­cyclo­[3.3.1]nonane-2,6-diol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(1R,2R,4S,5R,6R,8S)-4,8-Dimethyl-2,6-diphenylbicyclo[3.3.1]nonane-2,6-diol