(4aS,5R,7R,8S,8aR)-8-(1,3-Dioxolan-2-yl)-7,8-dimethyl-5-(1-methyl­ethen­yl)perhydro­naphthalen-2-one

Siegler, M.A.; Kooijman, H.; Spek, A.L.

doi:10.1107/S1600536807067335

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o337

https://doi.org/10.1107/S1600536807067335

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(4aS,5R,7R,8S,8aR)-8-(1,3-Dioxolan-2-yl)-7,8-dimethyl-5-(1-methylethenyl)perhydronaphthalen-2-one

Maxime A. Siegler,^a Huub Kooijman ^a ‡ and Anthony L. Spek ^a ^*

^aBijvoet Center for Biomolecular Research, Crystal and Structural Chemistry, Utrecht University, Padualaan 8, 3584 CH Utrecht, The Netherlands
^*Correspondence e-mail: a.l.spek@chem.uu.nl

(Received 10 December 2007; accepted 17 December 2007; online 21 December 2007)

In the chiral title compound, C₁₈H₂₈O₃, the two six-membered rings of the perhydronaphthalenone adopt a rigid chair–chair conformation and the five-membered dioxolanyl ring adopts an envelope conformation. The crystal structure is stabilized only by weak interactions.

Related literature

For related literature, see Meulemans et al. (1999 ); Meulemans & de Groot (2007 ); Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₈H₂₈O₃
M_r = 292.40
Monoclinic, P 2₁
a = 8.9172 (9) Å
b = 11.0318 (12) Å
c = 8.9616 (9) Å
β = 116.354 (6)°
V = 789.95 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 150 (2) K
0.30 × 0.30 × 0.30 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
6725 measured reflections
1678 independent reflections
1623 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.073
S = 1.07
1678 reflections
193 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Data collection: COLLECT (Nonius, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ); data reduction: DENZO; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807067335/si2067sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807067335/si2067Isup2.hkl

checkCIF report

Comment top

Crystals of the title compound (Fig. 1) were obtained as an undesired product as part of an attempt to synthesize a clerodane diterpenoid. The stereochemistry at each of the chiral centers (i.e., C5:S, C6:R, C8:R, C9:S, C10:R) was assigned based on the known chirality of C6:R of the starting material [i.e., R-(-)-carvone] (Meulemans et al.,1999).

The ring (C1/C2—C10) adopts a chair conformation with puckering parameters of Q = 0.559 (2) Å, θ = 173.5 (2)°, φ = 78.4(1.7)° (Cremer & Pople, 1975). The ring (C5/C6—C10) adopts a chair conformation with puckering parameters Q = 0.559 (2) Å, θ =176.2 (2)°, φ = 359 (3)°. The two six-membered rings of the hydronaphtalenone derivative adopt a rigid chair-chair conformation (i.e., the axial H atoms of the atoms C5 and C10 are located respectively below and above the best molecular plane of the octahydronaphtalen-2-one derivative).

The five-membered dioxolanyl ring (C11/O2—O3) adopts an envelope conformation on C17 (i.e., the atoms C11, C18, O2 and O3 are coplanar and C17 projects out of the plane) with puckering parameters of Q = 0.340 (2)Å and φ = 152.0 (3)°. The torsion angles C17 – O2 – C11 – O3 and C18 – O3 – C11 – O2 are respectively 26.80 (16) and -5.37 (17). Weak interactions are found between the equatorial H atom of atom C1 and atom C18 [C1–H1B···C18 (1 - x, 1/2 + y, -z) = 2.88 Å].

Other short contacts [C5···O1 (2 - x, -1/2 + y, -z) = 3.680 (2) Å and C13···O1 (2 - x, -1/2 + y, 1 - z) = 3.503 (2) Å] are also found in the crystal structure.

Related literature top

For related literature, see Meulemans et al. (1999); Meulemans & de Groot (2007); Cremer & Pople (1975).

Experimental top

Crystal of the title compound were obtained (Scheme 1) from Meulemans & de Groot (2007).

Structure description top

Other short contacts [C5···O1 (2 - x, -1/2 + y, -z) = 3.680 (2) Å and C13···O1 (2 - x, -1/2 + y, 1 - z) = 3.503 (2) Å] are also found in the crystal structure.

For related literature, see Meulemans et al. (1999); Meulemans & de Groot (2007); Cremer & Pople (1975).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. Displacement ellipsoid plot (50% probability level) of the asymmetric unit of the title compound at 150 K. H atoms are omitted for clarity.
	Fig. 2. The formation of the title compound.

(4aS,5R,7R,8S,8aR)-8-(1,3-Dioxolan-2-yl)-\7,8-dimethyl-5-(1-methylethenyl)perhydronaphthalen-2-one top

Crystal data top

C₁₈H₂₈O₃	F(000) = 320
M_r = 292.40	D_x = 1.229 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 225 reflections
a = 8.9172 (9) Å	θ = 2.0–20.0°
b = 11.0318 (12) Å	µ = 0.08 mm⁻¹
c = 8.9616 (9) Å	T = 150 K
β = 116.354 (6)°	Block, colourless
V = 789.95 (14) Å³	0.30 × 0.30 × 0.30 mm
Z = 2

Data collection top

Nonius KappaCCD diffractometer	1623 reflections with I > 2σ(I)
Radiation source: rotating anode	R_int = 0.034
Graphite monochromator	θ_max = 26.3°, θ_min = 2.5°
φ and ω scans	h = −11→11
6725 measured reflections	k = −13→13
1678 independent reflections	l = −11→10

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.028	H-atom parameters constrained
wR(F²) = 0.074	w = 1/[σ²(F_o²) + (0.0415P)² + 0.0975P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
1678 reflections	Δρ_max = 0.21 e Å⁻³
193 parameters	Δρ_min = −0.12 e Å⁻³
1 restraint	Absolute structure: known chirality of atom C6(R)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₈H₂₈O₃	V = 789.95 (14) Å³
M_r = 292.40	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.9172 (9) Å	µ = 0.08 mm⁻¹
b = 11.0318 (12) Å	T = 150 K
c = 8.9616 (9) Å	0.30 × 0.30 × 0.30 mm
β = 116.354 (6)°

Data collection top

Nonius KappaCCD diffractometer	1623 reflections with I > 2σ(I)
6725 measured reflections	R_int = 0.034
1678 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	1 restraint
wR(F²) = 0.074	H-atom parameters constrained
S = 1.07	Δρ_max = 0.21 e Å⁻³
1678 reflections	Δρ_min = −0.12 e Å⁻³
193 parameters	Absolute structure: known chirality of atom C6(R)

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
O1	0.91230 (16)	1.20580 (12)	0.02689 (16)	0.0341 (3)
O2	0.71825 (13)	0.66981 (11)	0.28172 (14)	0.0219 (3)
O3	0.66971 (14)	0.78772 (12)	0.05496 (14)	0.0252 (3)
C1	0.8606 (2)	1.01128 (16)	0.1128 (2)	0.0232 (4)
H1A	0.8318	0.9447	0.0306	0.028*
H1B	0.7548	1.0492	0.0998	0.028*
C2	0.9642 (2)	1.10439 (16)	0.07722 (19)	0.0226 (4)
C3	1.1366 (2)	1.06287 (16)	0.1097 (2)	0.0250 (4)
H3A	1.2019	1.1327	0.1008	0.030*
H3B	1.1282	1.0022	0.0250	0.030*
C4	1.22676 (19)	1.00670 (15)	0.2844 (2)	0.0209 (3)
H4A	1.3350	0.9725	0.2987	0.025*
H4B	1.2510	1.0713	0.3687	0.025*
C5	1.12471 (18)	0.90660 (14)	0.31573 (19)	0.0157 (3)
H5A	1.1045	0.8400	0.2333	0.019*
C6	1.22433 (18)	0.85501 (14)	0.49250 (19)	0.0166 (3)
H6A	1.2545	0.9245	0.5723	0.020*
C7	1.11779 (18)	0.76665 (14)	0.53733 (19)	0.0172 (3)
H7A	1.1830	0.7396	0.6540	0.021*
H7B	1.0928	0.6943	0.4649	0.021*
C8	0.95238 (19)	0.82285 (14)	0.51790 (19)	0.0162 (3)
H8A	0.8869	0.7565	0.5376	0.019*
C9	0.84606 (18)	0.86925 (14)	0.33675 (19)	0.0160 (3)
C10	0.95399 (18)	0.95839 (14)	0.29051 (19)	0.0159 (3)
H10A	0.9796	1.0286	0.3686	0.019*
C11	0.79211 (18)	0.75823 (15)	0.21959 (19)	0.0183 (3)
H11A	0.8927	0.7225	0.2142	0.022*
C12	0.68673 (19)	0.93240 (15)	0.3237 (2)	0.0218 (3)
H12A	0.6360	0.8833	0.3804	0.033*
H12B	0.6070	0.9416	0.2061	0.033*
H12C	0.7157	1.0125	0.3762	0.033*
C13	0.9859 (2)	0.91914 (16)	0.6532 (2)	0.0229 (3)
H13A	1.0418	0.9891	0.6327	0.034*
H13B	1.0576	0.8846	0.7627	0.034*
H13C	0.8795	0.9450	0.6503	0.034*
C14	1.38701 (19)	0.79469 (15)	0.51502 (19)	0.0196 (3)
C15	1.3778 (2)	0.70016 (18)	0.3920 (2)	0.0281 (4)
H15A	1.3457	0.7380	0.2831	0.042*
H15B	1.2942	0.6391	0.3826	0.042*
H15C	1.4874	0.6613	0.4294	0.042*
C16	1.5329 (2)	0.82505 (18)	0.6422 (2)	0.0284 (4)
H16A	1.6332	0.7863	0.6555	0.034*
H16B	1.5362	0.8854	0.7192	0.034*
C17	0.5970 (2)	0.60851 (16)	0.1386 (2)	0.0257 (4)
H17A	0.5079	0.5721	0.1616	0.031*
H17B	0.6495	0.5443	0.1004	0.031*
C18	0.5291 (2)	0.70922 (18)	0.0126 (2)	0.0290 (4)
H18A	0.4889	0.6777	−0.1022	0.035*
H18B	0.4360	0.7519	0.0221	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0380 (7)	0.0257 (7)	0.0346 (7)	0.0021 (6)	0.0126 (6)	0.0121 (6)
O2	0.0228 (6)	0.0192 (6)	0.0210 (6)	−0.0074 (5)	0.0073 (5)	−0.0009 (5)
O3	0.0228 (6)	0.0278 (6)	0.0189 (6)	−0.0096 (5)	0.0037 (5)	0.0007 (5)
C1	0.0176 (7)	0.0256 (8)	0.0229 (8)	−0.0005 (7)	0.0059 (6)	0.0072 (7)
C2	0.0269 (8)	0.0228 (8)	0.0156 (7)	−0.0027 (7)	0.0072 (6)	0.0028 (7)
C3	0.0265 (8)	0.0273 (9)	0.0235 (8)	−0.0047 (7)	0.0132 (7)	0.0047 (7)
C4	0.0177 (7)	0.0220 (8)	0.0237 (8)	−0.0019 (6)	0.0100 (6)	0.0043 (7)
C5	0.0149 (7)	0.0154 (7)	0.0163 (7)	−0.0006 (6)	0.0064 (6)	0.0000 (6)
C6	0.0162 (7)	0.0167 (7)	0.0170 (7)	0.0007 (6)	0.0074 (6)	0.0003 (6)
C7	0.0175 (7)	0.0149 (7)	0.0186 (7)	0.0008 (6)	0.0073 (6)	0.0024 (6)
C8	0.0172 (7)	0.0153 (7)	0.0167 (7)	−0.0011 (6)	0.0081 (6)	0.0011 (6)
C9	0.0147 (7)	0.0165 (7)	0.0179 (7)	0.0000 (6)	0.0081 (6)	0.0012 (6)
C10	0.0146 (7)	0.0149 (7)	0.0172 (7)	0.0008 (6)	0.0063 (6)	0.0027 (6)
C11	0.0175 (7)	0.0183 (7)	0.0181 (7)	−0.0020 (6)	0.0071 (6)	0.0000 (6)
C12	0.0177 (7)	0.0226 (8)	0.0266 (8)	0.0027 (6)	0.0111 (6)	0.0018 (7)
C13	0.0258 (8)	0.0242 (8)	0.0205 (8)	−0.0013 (7)	0.0120 (7)	−0.0027 (7)
C14	0.0182 (7)	0.0197 (8)	0.0215 (8)	0.0028 (6)	0.0093 (6)	0.0042 (6)
C15	0.0262 (8)	0.0277 (9)	0.0330 (9)	0.0070 (7)	0.0155 (7)	0.0005 (8)
C16	0.0204 (8)	0.0364 (10)	0.0267 (9)	0.0069 (7)	0.0088 (7)	0.0043 (8)
C17	0.0239 (8)	0.0245 (8)	0.0242 (8)	−0.0097 (7)	0.0067 (7)	−0.0038 (7)
C18	0.0205 (8)	0.0330 (9)	0.0262 (8)	−0.0104 (7)	0.0039 (7)	0.0012 (8)

Geometric parameters (Å, º) top

O1—C2	1.218 (2)	C8—C9	1.559 (2)
O2—C11	1.4215 (19)	C8—H8A	1.0000
O2—C17	1.428 (2)	C9—C12	1.539 (2)
O3—C18	1.430 (2)	C9—C11	1.544 (2)
O3—C11	1.4298 (18)	C9—C10	1.5554 (19)
C1—C2	1.507 (2)	C10—H10A	1.0000
C1—C10	1.547 (2)	C11—H11A	1.0000
C1—H1A	0.9900	C12—H12A	0.9800
C1—H1B	0.9900	C12—H12B	0.9800
C2—C3	1.503 (2)	C12—H12C	0.9800
C3—C4	1.537 (2)	C13—H13A	0.9800
C3—H3A	0.9900	C13—H13B	0.9800
C3—H3B	0.9900	C13—H13C	0.9800
C4—C5	1.534 (2)	C14—C16	1.337 (2)
C4—H4A	0.9900	C14—C15	1.493 (2)
C4—H4B	0.9900	C15—H15A	0.9800
C5—C6	1.541 (2)	C15—H15B	0.9800
C5—C10	1.5458 (19)	C15—H15C	0.9800
C5—H5A	1.0000	C16—H16A	0.9500
C6—C14	1.526 (2)	C16—H16B	0.9500
C6—C7	1.534 (2)	C17—C18	1.506 (3)
C6—H6A	1.0000	C17—H17A	0.9900
C7—C8	1.537 (2)	C17—H17B	0.9900
C7—H7A	0.9900	C18—H18A	0.9900
C7—H7B	0.9900	C18—H18B	0.9900
C8—C13	1.538 (2)

C11—O2—C17	105.72 (12)	C11—C9—C8	108.03 (12)
C18—O3—C11	108.30 (12)	C10—C9—C8	108.84 (11)
C2—C1—C10	111.98 (13)	C5—C10—C1	109.58 (12)
C2—C1—H1A	109.2	C5—C10—C9	114.40 (12)
C10—C1—H1A	109.2	C1—C10—C9	113.50 (12)
C2—C1—H1B	109.2	C5—C10—H10A	106.2
C10—C1—H1B	109.2	C1—C10—H10A	106.2
H1A—C1—H1B	107.9	C9—C10—H10A	106.2
O1—C2—C3	122.63 (16)	O2—C11—O3	106.63 (12)
O1—C2—C1	122.44 (16)	O2—C11—C9	109.67 (12)
C3—C2—C1	114.93 (14)	O3—C11—C9	112.69 (13)
C2—C3—C4	110.36 (13)	O2—C11—H11A	109.3
C2—C3—H3A	109.6	O3—C11—H11A	109.3
C4—C3—H3A	109.6	C9—C11—H11A	109.3
C2—C3—H3B	109.6	C9—C12—H12A	109.5
C4—C3—H3B	109.6	C9—C12—H12B	109.5
H3A—C3—H3B	108.1	H12A—C12—H12B	109.5
C5—C4—C3	113.07 (12)	C9—C12—H12C	109.5
C5—C4—H4A	109.0	H12A—C12—H12C	109.5
C3—C4—H4A	109.0	H12B—C12—H12C	109.5
C5—C4—H4B	109.0	C8—C13—H13A	109.5
C3—C4—H4B	109.0	C8—C13—H13B	109.5
H4A—C4—H4B	107.8	H13A—C13—H13B	109.5
C4—C5—C6	109.63 (12)	C8—C13—H13C	109.5
C4—C5—C10	109.45 (12)	H13A—C13—H13C	109.5
C6—C5—C10	111.58 (11)	H13B—C13—H13C	109.5
C4—C5—H5A	108.7	C16—C14—C15	121.22 (15)
C6—C5—H5A	108.7	C16—C14—C6	120.78 (15)
C10—C5—H5A	108.7	C15—C14—C6	118.00 (14)
C14—C6—C7	110.56 (12)	C14—C15—H15A	109.5
C14—C6—C5	112.18 (12)	C14—C15—H15B	109.5
C7—C6—C5	111.26 (12)	H15A—C15—H15B	109.5
C14—C6—H6A	107.5	C14—C15—H15C	109.5
C7—C6—H6A	107.5	H15A—C15—H15C	109.5
C5—C6—H6A	107.5	H15B—C15—H15C	109.5
C6—C7—C8	112.88 (12)	C14—C16—H16A	120.0
C6—C7—H7A	109.0	C14—C16—H16B	120.0
C8—C7—H7A	109.0	H16A—C16—H16B	120.0
C6—C7—H7B	109.0	O2—C17—C18	102.48 (14)
C8—C7—H7B	109.0	O2—C17—H17A	111.3
H7A—C7—H7B	107.8	C18—C17—H17A	111.3
C7—C8—C13	110.40 (12)	O2—C17—H17B	111.3
C7—C8—C9	111.09 (12)	C18—C17—H17B	111.3
C13—C8—C9	114.17 (13)	H17A—C17—H17B	109.2
C7—C8—H8A	106.9	O3—C18—C17	103.57 (13)
C13—C8—H8A	106.9	O3—C18—H18A	111.0
C9—C8—H8A	106.9	C17—C18—H18A	111.0
C12—C9—C11	107.98 (12)	O3—C18—H18B	111.0
C12—C9—C10	110.66 (12)	C17—C18—H18B	111.0
C11—C9—C10	111.29 (12)	H18A—C18—H18B	109.0
C12—C9—C8	110.00 (12)

C10—C1—C2—O1	−126.84 (17)	C2—C1—C10—C5	−55.17 (18)
C10—C1—C2—C3	52.74 (19)	C2—C1—C10—C9	175.58 (13)
O1—C2—C3—C4	129.35 (17)	C12—C9—C10—C5	174.62 (12)
C1—C2—C3—C4	−50.2 (2)	C11—C9—C10—C5	−65.32 (16)
C2—C3—C4—C5	52.91 (19)	C8—C9—C10—C5	53.62 (16)
C3—C4—C5—C6	179.67 (13)	C12—C9—C10—C1	−58.63 (17)
C3—C4—C5—C10	−57.64 (17)	C11—C9—C10—C1	61.44 (16)
C4—C5—C6—C14	−63.06 (16)	C8—C9—C10—C1	−179.62 (12)
C10—C5—C6—C14	175.53 (13)	C17—O2—C11—O3	26.80 (16)
C4—C5—C6—C7	172.49 (12)	C17—O2—C11—C9	149.10 (12)
C10—C5—C6—C7	51.08 (16)	C18—O3—C11—O2	−5.37 (17)
C14—C6—C7—C8	179.67 (12)	C18—O3—C11—C9	−125.73 (14)
C5—C6—C7—C8	−54.97 (17)	C12—C9—C11—O2	−67.98 (15)
C6—C7—C8—C13	−70.08 (16)	C10—C9—C11—O2	170.38 (12)
C6—C7—C8—C9	57.63 (16)	C8—C9—C11—O2	50.96 (15)
C7—C8—C9—C12	−176.34 (13)	C12—C9—C11—O3	50.63 (16)
C13—C8—C9—C12	−50.71 (16)	C10—C9—C11—O3	−71.01 (15)
C7—C8—C9—C11	66.02 (15)	C8—C9—C11—O3	169.56 (11)
C13—C8—C9—C11	−168.35 (12)	C7—C6—C14—C16	−107.18 (17)
C7—C8—C9—C10	−54.94 (15)	C5—C6—C14—C16	127.98 (17)
C13—C8—C9—C10	70.69 (15)	C7—C6—C14—C15	72.20 (18)
C4—C5—C10—C1	57.34 (16)	C5—C6—C14—C15	−52.63 (19)
C6—C5—C10—C1	178.86 (13)	C11—O2—C17—C18	−36.40 (16)
C4—C5—C10—C9	−173.90 (12)	C11—O3—C18—C17	−16.77 (18)
C6—C5—C10—C9	−52.38 (16)	O2—C17—C18—O3	32.42 (17)

Experimental details

Crystal data
Chemical formula	C₁₈H₂₈O₃
M_r	292.40
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	150
a, b, c (Å)	8.9172 (9), 11.0318 (12), 8.9616 (9)
β (°)	116.354 (6)
V (Å³)	789.95 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.30 × 0.30

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6725, 1678, 1623
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.074, 1.07
No. of reflections	1678
No. of parameters	193
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.12
Absolute structure	Known chirality of atom C6(R)

Computer programs: COLLECT (Nonius, 1998), DENZO (Otwinowski & Minor, 1997), SHELXS86 (Sheldrick, 1985), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Footnotes

‡Shell Global Solutions International BV, Badhuisweg 3, 1031 CM Amsterdam, PO Box 38000, 1030 BN Amsterdam, The Netherlands.

Acknowledgements

We are grateful to Dr Tommy M. Meulemans and Professor Aede de Groot for providing crystals of the title compound. This work was supported by the Council for Chemical Sciences of the Netherlands Organization for Scientific Research (CW–NWO).

References

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Meulemans, T. M. & de Groot, A. E. (2007). Private communication. Google Scholar
Meulemans, T. M., Stork, G. A., Macaev, F. Z., Jansen, B. J. M. & de Groot, A. (1999). J. Org. Chem. 64, 9178–9188. Web of Science CrossRef CAS Google Scholar
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (1985). SHELXS86. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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