(2R,4R)-2-Hydr­oxy-4-(2-methoxy­phen­yl)bicyclo­[3.3.1]nonan-9-one

Luo, S.; Zhang, G.; Zhang, S.; Wang, Y.; Zhang, W.

doi:10.1107/S1600536809028980

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o2012

doi:10.1107/S1600536809028980

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(2R,4R)-2-Hydroxy-4-(2-methoxyphenyl)bicyclo[3.3.1]nonan-9-one

Shuping Luo,^a ^* Guangcun Zhang,^a Shuai Zhang,^a Yifeng Wang ^a and Wei Zhang ^a

^aState Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: lsp96@163.com

(Received 3 July 2009; accepted 22 July 2009; online 29 July 2009)

The title compound, C₁₆H₂₀O₃, contains a bicyclic ring system with two chiral centers. The crystal structure is stabilized by intermolecular O—H⋯O hydrogen bonds. The absolute configuration was established by the stereo-selectivity of the asymmetric organocatalysis.

Related literature

A similar structure is described by Cao et al. (2007 ). For general background to organocatalysis, see: List et al. (2000 , 2001 ); Notz et al. (2001 ).

Experimental

Crystal data

C₁₆H₂₀O₃
M_r = 260.33
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.9378 (5) Å
b = 12.5291 (11) Å
c = 16.0726 (14) Å
V = 1397.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.47 × 0.32 × 0.29 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.945, T_max = 0.976
13314 measured reflections
1840 independent reflections
1211 reflections with F² > 2σ(F²)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.061
S = 1.00
1840 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H101⋯O2ⁱ	0.85	1.99	2.8268 (19)	171
O1ⁱⁱ—H101ⁱⁱ⋯O2	0.85	1.99	2.8268 (19)	171
C14—H14⋯O1ⁱⁱⁱ	0.93	2.51	3.434 (2)	176
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z]$ ; (ii) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, -z]$ ; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 2006 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ), and Larson (1970 ); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809028980/zl2227sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028980/zl2227Isup2.hkl

checkCIF report

Comment top

The natural amino acid L-proline, pioneered by List and Barbas III and their co-workers, has been fully appreciated as an attractive enantioselective organocatalyst for direct asymmetric carbon-carbon and carbon-heteroatom bond-forming reactions, such as aldol (List et al., 2000), Mannich (List et al., 2001) and Michael (Notz et al., 2000) reactions. In our laboratory, a novel tandem Michael-aldol reaction of ketones with cinnamaldehyde derivatives catalyzed by L-proline was developed and a series of new products was obtained. The crystal structure of one of these, the title compound, is reported in this article.

In the crystal structure of the title compound (Fig. 1), both bicyclic six-membered rings display chair conformations in which atoms C1, C8, C4, C3 and atoms C4, C8, C7, C5 each lie in an approximate plane with the dihedral angle between them being 115.9 (0)°. C9 is located above the two planes with similar dihedral angles. The hydroxyl group and the phenyl group are located on different sides of the plane made up of atoms C1, C8, C4, C3. The hydroxyl group is in an axial position, the phenyl group in an equatorial position of the cyclohexanone ring.

Intermolecular O—H···O hydrogen bonds (Tab. 1) connect neighboring molecules with each other to form a one-dimensional chain that stretches along the direction of the a axis (Fig. 2). Via weak C—H···O hydrogen bonds (Tab. 1) molecules are linked along the b axis to form another one-dimensional chain.

Related literature top

A similar structure is described by Cao et al. (2007). For general background to organocatalysis, see: List et al. (2000, 2001); Notz et al. (2001).

Experimental top

A DMF (2 ml) solution of cyclohexanone and 3-(2-methoxyphenyl)acryaldehyde in the presence of L-proline as organocatalyst was stirred at room temperature for 48 h. Then the mixture was washed with water (20 ml) and extracted with ethyl acetate (three times). The organic solvent was removed under reduced pressure and the product was purified by silica gel chromatography (pentane: ethyl acetate mixtures). Suitable crystals were obtained by slow evaporation of ethanol at room temperature.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 2006); cell refinement: PROCESS-AUTO (Rigaku, 2006); data reduction: CrystalStructure (Rigaku/MSC, 2004), and Larson (1970); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004).

Figures top

	Fig. 1. Thermal ellipsoid representation of the of title compound with the atomic labeling scheme. Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. View of the hydrogen bonding interactions. H bonds are represented as dashed lines. Symmetery codes: (i) x + 1/2, -y - 1/2, -z. (iv) -x, y + 1/2, 1/2 -z. (v) 1/2 - x, -y - 1, - 1/2 + z.

(2R,4R)-2-Hydroxy-4-(2-methoxyphenyl)bicyclo[3.3.1]nonan-9-one top

Crystal data top

C₁₆H₂₀O₃	F(000) = 560.00
M_r = 260.33	D_x = 1.238 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8871 reflections
a = 6.9378 (5) Å	θ = 3.0–27.4°
b = 12.5291 (11) Å	µ = 0.08 mm⁻¹
c = 16.0726 (14) Å	T = 296 K
V = 1397.1 (2) Å³	Chunk, colorless
Z = 4	0.47 × 0.32 × 0.29 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	1211 reflections with F² > 2σ(F²)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.034
ω scans	θ_max = 27.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→8
T_min = 0.945, T_max = 0.976	k = −16→16
13314 measured reflections	l = −20→20
1840 independent reflections

Refinement top

Refinement on F²	w = 1/[1.01σ(F_o²)]/(4F_o²)
R[F² > 2σ(F²)] = 0.032	(Δ/σ)_max < 0.001
wR(F²) = 0.061	Δρ_max = 0.16 e Å⁻³
S = 1.00	Δρ_min = −0.13 e Å⁻³
1840 reflections	Extinction correction: Larson (1970), equation 22
173 parameters	Extinction coefficient: 649 (27)
H-atom parameters constrained

Crystal data top

C₁₆H₂₀O₃	V = 1397.1 (2) Å³
M_r = 260.33	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.9378 (5) Å	µ = 0.08 mm⁻¹
b = 12.5291 (11) Å	T = 296 K
c = 16.0726 (14) Å	0.47 × 0.32 × 0.29 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	1840 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1211 reflections with F² > 2σ(F²)
T_min = 0.945, T_max = 0.976	R_int = 0.034
13314 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	173 parameters
wR(F²) = 0.061	H-atom parameters constrained
S = 1.00	Δρ_max = 0.16 e Å⁻³
1840 reflections	Δρ_min = −0.13 e Å⁻³

Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	U_iso*/U_eq
O1	0.3084 (2)	−0.19303 (10)	0.07830 (9)	0.0638 (4)
O2	−0.1217 (2)	−0.10943 (12)	0.00114 (9)	0.0622 (4)
O3	−0.10291 (19)	0.08144 (11)	0.23327 (8)	0.0593 (4)
C1	0.1869 (2)	0.03037 (14)	0.12399 (11)	0.0390 (5)
C2	0.3817 (2)	−0.00912 (14)	0.09036 (12)	0.0457 (5)
C3	0.3617 (2)	−0.10201 (16)	0.02981 (12)	0.0476 (5)
C4	0.2100 (2)	−0.08335 (16)	−0.03793 (12)	0.0472 (5)
C5	0.2559 (3)	0.00623 (18)	−0.10098 (12)	0.0601 (6)
C6	0.2481 (3)	0.11937 (17)	−0.06523 (13)	0.0657 (7)
C7	0.0787 (3)	0.13738 (16)	−0.00841 (12)	0.0599 (6)
C8	0.0362 (2)	0.04651 (14)	0.05297 (12)	0.0433 (5)
C9	0.0240 (2)	−0.05569 (16)	0.00463 (12)	0.0440 (5)
C10	0.1996 (2)	0.12898 (14)	0.17882 (11)	0.0388 (5)
C11	0.3544 (2)	0.19787 (16)	0.17853 (12)	0.0519 (6)
C12	0.3625 (3)	0.28667 (17)	0.23012 (12)	0.0653 (7)
C13	0.2124 (3)	0.30819 (18)	0.28234 (13)	0.0632 (7)
C14	0.0528 (3)	0.24199 (16)	0.28470 (12)	0.0527 (6)
C15	0.0475 (2)	0.15310 (14)	0.23345 (12)	0.0437 (5)
C16	−0.2463 (2)	0.0914 (2)	0.29575 (13)	0.0707 (7)
H1	0.1366	−0.0270	0.1593	0.047*
H3	0.4868	−0.1155	0.0035	0.057*
H4	0.1918	−0.1502	−0.0687	0.057*
H8	−0.0897	0.0599	0.0785	0.052*
H11	0.4567	0.1845	0.1426	0.062*
H12	0.4697	0.3312	0.2291	0.078*
H13	0.2174	0.3679	0.3167	0.076*
H14	−0.0495	0.2570	0.3202	0.063*
H21	0.4604	−0.0320	0.1369	0.055*
H22	0.4448	0.0495	0.0619	0.055*
H51	0.3847	−0.0058	−0.1226	0.072*
H52	0.1634	0.0017	−0.1461	0.072*
H61	0.3655	0.1322	−0.0341	0.079*
H62	0.2399	0.1696	−0.1110	0.079*
H71	−0.0348	0.1477	−0.0427	0.072*
H72	0.1032	0.2016	0.0236	0.072*
H101	0.3263	−0.2488	0.0498	0.077*
H161	−0.3243	0.0282	0.2967	0.085*
H162	−0.1856	0.1007	0.3489	0.085*
H163	−0.3260	0.1522	0.2839	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0884 (9)	0.0367 (7)	0.0664 (9)	0.0155 (8)	0.0188 (8)	0.0031 (7)
O2	0.0536 (7)	0.0633 (10)	0.0698 (10)	−0.0144 (8)	−0.0018 (8)	−0.0159 (9)
O3	0.0580 (7)	0.0607 (9)	0.0591 (9)	−0.0141 (8)	0.0173 (7)	−0.0219 (7)
C1	0.0433 (9)	0.0327 (10)	0.0410 (10)	0.0023 (8)	0.0029 (8)	−0.0021 (8)
C2	0.0448 (10)	0.0422 (11)	0.0502 (12)	0.0061 (10)	−0.0038 (9)	−0.0003 (10)
C3	0.0494 (11)	0.0398 (11)	0.0537 (12)	0.0076 (10)	0.0110 (10)	−0.0023 (10)
C4	0.0553 (11)	0.0392 (11)	0.0472 (11)	−0.0009 (10)	0.0070 (10)	−0.0121 (9)
C5	0.0638 (13)	0.0677 (14)	0.0488 (12)	0.0024 (13)	0.0070 (11)	0.0001 (11)
C6	0.0879 (16)	0.0525 (14)	0.0566 (14)	−0.0027 (14)	−0.0052 (13)	0.0114 (12)
C7	0.0857 (15)	0.0436 (12)	0.0503 (12)	0.0147 (12)	−0.0154 (12)	−0.0024 (11)
C8	0.0421 (9)	0.0428 (11)	0.0452 (10)	0.0068 (9)	−0.0030 (9)	−0.0122 (10)
C9	0.0454 (10)	0.0447 (11)	0.0420 (11)	−0.0015 (10)	−0.0025 (9)	−0.0042 (10)
C10	0.0491 (10)	0.0333 (10)	0.0341 (9)	0.0000 (9)	−0.0037 (9)	−0.0003 (8)
C11	0.0595 (12)	0.0452 (11)	0.0509 (12)	−0.0091 (11)	0.0081 (10)	−0.0048 (10)
C12	0.0772 (14)	0.0512 (14)	0.0675 (15)	−0.0229 (13)	0.0124 (13)	−0.0159 (12)
C13	0.0856 (15)	0.0440 (13)	0.0600 (14)	−0.0115 (13)	0.0037 (13)	−0.0156 (11)
C14	0.0650 (13)	0.0442 (12)	0.0488 (12)	0.0023 (11)	0.0065 (11)	−0.0104 (10)
C15	0.0519 (11)	0.0396 (11)	0.0397 (11)	−0.0022 (9)	−0.0024 (10)	−0.0023 (10)
C16	0.0503 (12)	0.0801 (17)	0.0816 (16)	−0.0057 (13)	0.0152 (12)	−0.0221 (14)

Geometric parameters (Å, º) top

O1—C3	1.430 (2)	O1—H101	0.846
O2—C9	1.216 (2)	C1—H1	0.980
O3—C15	1.376 (2)	C2—H21	0.970
O3—C16	1.419 (2)	C2—H22	0.970
C1—C2	1.537 (2)	C3—H3	0.980
C1—C8	1.561 (2)	C4—H4	0.980
C1—C10	1.520 (2)	C5—H51	0.970
C2—C3	1.523 (2)	C5—H52	0.970
C3—C4	1.533 (2)	C6—H61	0.970
C4—C5	1.545 (2)	C6—H62	0.970
C4—C9	1.501 (2)	C7—H71	0.970
C5—C6	1.531 (3)	C7—H72	0.970
C6—C7	1.505 (3)	C8—H8	0.980
C7—C8	1.535 (2)	C11—H11	0.930
C8—C9	1.500 (2)	C12—H12	0.930
C10—C11	1.378 (2)	C13—H13	0.930
C10—C15	1.406 (2)	C14—H14	0.930
C11—C12	1.389 (2)	C16—H161	0.960
C12—C13	1.365 (3)	C16—H162	0.960
C13—C14	1.384 (3)	C16—H163	0.960
C14—C15	1.386 (2)

C15—O3—C16	118.18 (15)	O1—C3—H3	109.1
C2—C1—C8	111.91 (14)	C2—C3—H3	109.1
C2—C1—C10	114.46 (14)	C4—C3—H3	109.1
C8—C1—C10	110.96 (14)	C3—C4—H4	108.4
C1—C2—C3	112.99 (15)	C5—C4—H4	108.4
O1—C3—C2	106.53 (15)	C9—C4—H4	108.4
O1—C3—C4	109.33 (15)	C4—C5—H51	108.1
C2—C3—C4	113.56 (16)	C4—C5—H52	108.1
C3—C4—C5	115.78 (16)	C6—C5—H51	108.1
C3—C4—C9	107.58 (15)	C6—C5—H52	108.1
C5—C4—C9	107.97 (16)	H51—C5—H52	109.5
C4—C5—C6	114.78 (17)	C5—C6—H61	108.5
C5—C6—C7	113.23 (18)	C5—C6—H62	108.5
C6—C7—C8	115.36 (16)	C7—C6—H61	108.5
C1—C8—C7	115.97 (15)	C7—C6—H62	108.5
C1—C8—C9	107.82 (15)	H61—C6—H62	109.5
C7—C8—C9	108.12 (15)	C6—C7—H71	108.0
O2—C9—C4	124.46 (18)	C6—C7—H72	108.0
O2—C9—C8	122.92 (17)	C8—C7—H71	108.0
C4—C9—C8	112.62 (15)	C8—C7—H72	108.0
C1—C10—C11	123.56 (16)	H71—C7—H72	109.5
C1—C10—C15	119.53 (16)	C1—C8—H8	108.2
C11—C10—C15	116.91 (17)	C7—C8—H8	108.2
C10—C11—C12	122.11 (19)	C9—C8—H8	108.2
C11—C12—C13	119.6 (2)	C10—C11—H11	118.9
C12—C13—C14	120.6 (2)	C12—C11—H11	118.9
C13—C14—C15	119.12 (19)	C11—C12—H12	120.2
O3—C15—C10	115.32 (16)	C13—C12—H12	120.2
O3—C15—C14	123.07 (17)	C12—C13—H13	119.7
C10—C15—C14	121.60 (17)	C14—C13—H13	119.7
C3—O1—H101	109.0	C13—C14—H14	120.4
C2—C1—H1	106.3	C15—C14—H14	120.4
C8—C1—H1	106.3	O3—C16—H161	109.5
C10—C1—H1	106.3	O3—C16—H162	109.5
C1—C2—H21	108.6	O3—C16—H163	109.5
C1—C2—H22	108.6	H161—C16—H162	109.5
C3—C2—H21	108.6	H161—C16—H163	109.5
C3—C2—H22	108.6	H162—C16—H163	109.5
H21—C2—H22	109.5

C16—O3—C15—C10	170.27 (16)	C5—C4—C9—C8	−62.1 (2)
C16—O3—C15—C14	−8.4 (2)	C9—C4—C5—C6	50.9 (2)
C2—C1—C8—C7	−67.5 (2)	C4—C5—C6—C7	−42.5 (2)
C2—C1—C8—C9	53.83 (19)	C5—C6—C7—C8	42.9 (2)
C8—C1—C2—C3	−47.7 (2)	C6—C7—C8—C1	69.4 (2)
C2—C1—C10—C11	19.8 (2)	C6—C7—C8—C9	−51.8 (2)
C2—C1—C10—C15	−160.11 (16)	C1—C8—C9—O2	116.16 (19)
C10—C1—C2—C3	−175.04 (15)	C1—C8—C9—C4	−63.67 (19)
C8—C1—C10—C11	−108.0 (2)	C7—C8—C9—O2	−117.7 (2)
C8—C1—C10—C15	72.1 (2)	C7—C8—C9—C4	62.4 (2)
C10—C1—C8—C7	61.7 (2)	C1—C10—C11—C12	−179.26 (18)
C10—C1—C8—C9	−176.97 (14)	C1—C10—C15—O3	1.2 (2)
C1—C2—C3—O1	−71.93 (19)	C1—C10—C15—C14	179.90 (17)
C1—C2—C3—C4	48.5 (2)	C11—C10—C15—O3	−178.77 (16)
O1—C3—C4—C5	−174.64 (15)	C11—C10—C15—C14	−0.0 (2)
O1—C3—C4—C9	64.54 (19)	C15—C10—C11—C12	0.7 (2)
C2—C3—C4—C5	66.5 (2)	C10—C11—C12—C13	−0.9 (3)
C2—C3—C4—C9	−54.3 (2)	C11—C12—C13—C14	0.4 (3)
C3—C4—C5—C6	−69.7 (2)	C12—C13—C14—C15	0.2 (3)
C3—C4—C9—O2	−116.3 (2)	C13—C14—C15—O3	178.22 (18)
C3—C4—C9—C8	63.5 (2)	C13—C14—C15—C10	−0.4 (2)
C5—C4—C9—O2	118.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H101···O2ⁱ	0.85	1.99	2.8268 (19)	171
O1ⁱⁱ—H101ⁱⁱ···O2	0.85	1.99	2.8268 (19)	171
C14—H14···O1ⁱⁱⁱ	0.93	2.51	3.434 (2)	176

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

Experimental details

Crystal data
Chemical formula	C₁₆H₂₀O₃
M_r	260.33
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	6.9378 (5), 12.5291 (11), 16.0726 (14)
V (Å³)	1397.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.47 × 0.32 × 0.29

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.945, 0.976
No. of measured, independent and observed [F² > 2σ(F²)] reflections	13314, 1840, 1211
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.061, 1.00
No. of reflections	1840
No. of parameters	173
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.13

Computer programs: PROCESS-AUTO (Rigaku, 2006), CrystalStructure (Rigaku/MSC, 2004), and Larson (1970), SIR97 (Altomare et al., 1999), CRYSTALS (Watkin et al., 1996), ORTEP-3 for Windows (Farrugia, 1997), CrystalStructure (Rigaku/MSC, 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H101···O2ⁱ	0.846	1.988	2.8268 (19)	171.3
O1ⁱⁱ—H101ⁱⁱ···O2	0.846	1.988	2.8268 (19)	171.3
C14—H14···O1ⁱⁱⁱ	0.930	2.506	3.434 (2)	176.0

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

Acknowledgements

We acknowledge the help of Professor Jianming Gu of Zhejiang University. We are also grateful for financial support from the Natural Science Foundation of Zhejiang Province Education Department (No. Y200803565).

References

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