(1S,2S,4R)-7-tert-But­oxy­bicyclo­[2.2.1]hept-5-en-2-yl (2S)-2-(6-meth­oxy­naphthalen-2-yl)propano­ate

Lough, A.J.; Petrone, D.A.; Tam, W.

doi:10.1107/S1600536811024238

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1848

doi:10.1107/S1600536811024238

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(1S,2S,4R)-7-tert-Butoxybicyclo[2.2.1]hept-5-en-2-yl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate

Alan J. Lough,^a ^* David A. Petrone ^b and William Tam ^b

^aDepartment of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6, and ^bDepartment of Chemistry, University of Guelph, Guelph, Ontario, Canada N1G 2W1
^*Correspondence e-mail: alough@chem.utoronto.ca

(Received 13 June 2011; accepted 20 June 2011; online 30 June 2011)

In the title molecule, C₂₅H₃₀O₄, the napthalene ring system is slightly bowed, with a dihedral angle of 4.37 (13)° between the two benzene rings.

Related literature

For the synthesis of anti-2,7-disubstituted norbornadienes from racemic 7-tert-butoxy-bicyclo[2.2.1]hepta-5-en-2-ol, see: Tsui et al. (2009 ).

Experimental

Crystal data

C₂₅H₃₀O₄
M_r = 394.49
Monoclinic, P 2₁
a = 11.8328 (11) Å
b = 6.0084 (4) Å
c = 15.2205 (15) Å
β = 96.705 (4)°
V = 1074.72 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 150 K
0.50 × 0.20 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.480, T_max = 0.990
8333 measured reflections
2649 independent reflections
2023 reflections with I > 2σ(I)
R_int = 0.071

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.122
S = 1.05
2649 reflections
267 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: COLLECT (Nonius, 2002 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811024238/pk2333sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024238/pk2333Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811024238/pk2333Isup3.cml

checkCIF report

Comment top

Recently, we have investigated the synthesis of anti-2,7-disubstituted norbornadienes from racemic 7-tert-butoxy-bicyclo[2.2.1]hepta-5-en-2-ol (±) (I) (Tsui et al., 2009). In order to synthesize a chiral anti-2,7-disubstituted norbornadiene, we have studied the resolution of the racemic mixture of 7-tert-butoxy-bicyclo[2.2.1]hepta-5-en-2-ol (±) (I) through the use of α-chiral carboxylic acids as resolving agents. We found that when (S)-(+)-6-methoxy-α-methyl-2-naphthaleneacetic acid (II) (See Fig. 2) is used as the resolving agent, the diastereomeric mixture of (III) and (IV) is obtained. This mixture has been resolved using fractional crystallization which afforded diastereomer (IV) with dr > 99:1. The absolute position of the ester on the bicyclic framework has been elucidated by this single-crystal x-ray analysis.

Related literature top

For the synthesis of anti-2,7-disubstituted norbornadienes from racemic 7-tert-butoxy-bicyclo[2.2.1]hepta-5-en-2-ol, see: Tsui et al. (2009).

Experimental top

7-tert-butoxy-bicyclo[2.2.1]hepta-5-en-2-ol (±)-I (1.2 g, 6.4 mmol), (S)-(+)-6-methoxy-a-methyl-2-napthaleneacetic acid (II) (1.63 g, 7.08 mmol), DCC (1.58 g, 7.68 mmol), and DMAP (0.156 g, 1.28 mmol) were weighted into a dry round bottom flask and purged with nitrogen. Dried CH₂Cl₂ (64 ml) was added through a vented septum to dissolve all solids forming a 0.1 M solution with respect to (±)-I. The reaction vessel was sealed and its contents were stirred at room temperature for 21 h while monitoring the reaction progression by TLC. The crude product was purified using flash column chromatography (EtOAc:hexanes = 30:70) to provide diastereomers (III) and (IV) in equal ratio as an off white semi-solid (2.33 g, 5.9 mmol, 92%). Fractional crystallization with MeOH was used to separate these species and to grow suitable crystals of (IV).

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probabilty level.
	Fig. 2. The reaction scheme

(1S,2S,4R)-7-tert-Butoxybicyclo[2.2.1]hept-5-en-2-yl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate top

Crystal data top

C₂₅H₃₀O₄	F(000) = 424
M_r = 394.49	D_x = 1.219 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 8333 reflections
a = 11.8328 (11) Å	θ = 2.7–27.5°
b = 6.0084 (4) Å	µ = 0.08 mm⁻¹
c = 15.2205 (15) Å	T = 150 K
β = 96.705 (4)°	Needle, colourless
V = 1074.72 (16) Å³	0.50 × 0.20 × 0.12 mm
Z = 2

Data collection top

Nonius KappaCCD diffractometer	2649 independent reflections
Radiation source: fine-focus sealed tube	2023 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 2.7°
ϕ scans and ω scans with κ offsets	h = −15→15
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −7→6
T_min = 0.480, T_max = 0.990	l = −16→19
8333 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0605P)² + 0.0914P] where P = (F_o² + 2F_c²)/3
2649 reflections	(Δ/σ)_max < 0.001
267 parameters	Δρ_max = 0.16 e Å⁻³
1 restraint	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₅H₃₀O₄	V = 1074.72 (16) Å³
M_r = 394.49	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 11.8328 (11) Å	µ = 0.08 mm⁻¹
b = 6.0084 (4) Å	T = 150 K
c = 15.2205 (15) Å	0.50 × 0.20 × 0.12 mm
β = 96.705 (4)°

Data collection top

Nonius KappaCCD diffractometer	2649 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	2023 reflections with I > 2σ(I)
T_min = 0.480, T_max = 0.990	R_int = 0.071
8333 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	1 restraint
wR(F²) = 0.122	H-atom parameters constrained
S = 1.05	Δρ_max = 0.16 e Å⁻³
2649 reflections	Δρ_min = −0.25 e Å⁻³
267 parameters

Special details top

Experimental. multi-scan from symmetry-related measurements (SORTAV (Blessing 1995)

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 > σ(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	0.69010 (15)	0.8083 (4)	0.08425 (13)	0.0433 (5)
O2	0.58736 (15)	0.8603 (3)	0.34025 (12)	0.0371 (4)
O3	0.49435 (16)	0.5653 (4)	0.38828 (14)	0.0478 (5)
O4	1.21074 (16)	0.2459 (4)	0.25951 (14)	0.0490 (5)
C1	0.5058 (2)	0.8713 (5)	0.26074 (17)	0.0378 (6)
H1A	0.4278	0.8258	0.2729	0.045*
C2	0.5477 (2)	0.7305 (5)	0.18658 (18)	0.0368 (6)
H2A	0.5760	0.5779	0.2037	0.044*
C3	0.4558 (2)	0.7435 (5)	0.10890 (19)	0.0430 (7)
H3	0.4070	0.6258	0.0866	0.052*
C4	0.4559 (2)	0.9493 (5)	0.0778 (2)	0.0430 (7)
H4	0.4061	1.0059	0.0295	0.052*
C5	0.5482 (2)	1.0785 (5)	0.13189 (18)	0.0406 (7)
H5A	0.5767	1.2140	0.1033	0.049*
C6	0.5073 (2)	1.1131 (5)	0.2247 (2)	0.0407 (7)
H6A	0.5610	1.2079	0.2629	0.049*
H6B	0.4306	1.1809	0.2196	0.049*
C7	0.6362 (2)	0.8921 (5)	0.15578 (18)	0.0377 (6)
H7A	0.6934	0.9373	0.2062	0.045*
C8	0.8098 (2)	0.8585 (6)	0.0853 (2)	0.0432 (7)
C9	0.8780 (3)	0.7327 (6)	0.1619 (2)	0.0514 (8)
H9A	0.8590	0.5740	0.1578	0.077*
H9B	0.8589	0.7916	0.2184	0.077*
H9C	0.9596	0.7524	0.1585	0.077*
C10	0.8387 (3)	0.7701 (6)	−0.0023 (2)	0.0559 (9)
H10A	0.8232	0.6099	−0.0059	0.084*
H10B	0.9194	0.7965	−0.0072	0.084*
H10C	0.7922	0.8465	−0.0507	0.084*
C11	0.8306 (3)	1.1075 (6)	0.0922 (2)	0.0506 (8)
H11A	0.7856	1.1829	0.0428	0.076*
H11B	0.9116	1.1379	0.0900	0.076*
H11C	0.8082	1.1624	0.1483	0.076*
C12	0.5739 (2)	0.6939 (5)	0.39715 (18)	0.0364 (6)
C13	0.6718 (2)	0.6822 (5)	0.46982 (18)	0.0374 (6)
H13A	0.6969	0.8371	0.4863	0.045*
C14	0.6351 (3)	0.5668 (6)	0.55187 (19)	0.0474 (7)
H14A	0.5719	0.6494	0.5727	0.071*
H14B	0.6993	0.5629	0.5987	0.071*
H14C	0.6105	0.4145	0.5366	0.071*
C15	0.7694 (2)	0.5613 (5)	0.43366 (17)	0.0359 (6)
C16	0.8758 (2)	0.6525 (5)	0.43437 (18)	0.0384 (6)
H16A	0.8912	0.7933	0.4616	0.046*
C17	0.9630 (2)	0.5422 (5)	0.39564 (18)	0.0376 (6)
C18	1.0740 (2)	0.6343 (5)	0.3944 (2)	0.0437 (7)
H18A	1.0928	0.7709	0.4240	0.052*
C19	1.1535 (2)	0.5292 (5)	0.3513 (2)	0.0448 (7)
H19A	1.2271	0.5925	0.3518	0.054*
C20	1.1274 (2)	0.3266 (5)	0.30572 (19)	0.0422 (7)
C21	1.0239 (2)	0.2270 (5)	0.31015 (18)	0.0396 (6)
H21A	1.0083	0.0867	0.2825	0.048*
C22	0.9399 (2)	0.3308 (5)	0.35548 (18)	0.0370 (6)
C23	0.8319 (2)	0.2348 (5)	0.35925 (18)	0.0386 (6)
H23A	0.8163	0.0910	0.3349	0.046*
C24	0.7492 (2)	0.3453 (5)	0.39745 (18)	0.0377 (6)
H24A	0.6773	0.2766	0.3998	0.045*
C25	1.1868 (3)	0.0424 (6)	0.2127 (2)	0.0524 (8)
H25A	1.2504	0.0054	0.1794	0.079*
H25B	1.1171	0.0592	0.1716	0.079*
H25C	1.1765	−0.0771	0.2548	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0389 (10)	0.0518 (12)	0.0400 (11)	−0.0032 (9)	0.0080 (8)	−0.0110 (9)
O2	0.0376 (10)	0.0382 (11)	0.0349 (10)	−0.0034 (9)	0.0014 (8)	0.0028 (9)
O3	0.0458 (11)	0.0428 (12)	0.0533 (13)	−0.0078 (11)	−0.0001 (9)	0.0072 (11)
O4	0.0406 (11)	0.0560 (14)	0.0512 (13)	0.0009 (10)	0.0087 (9)	0.0020 (11)
C1	0.0360 (14)	0.0447 (16)	0.0323 (14)	−0.0030 (13)	0.0021 (11)	0.0009 (13)
C2	0.0401 (15)	0.0320 (14)	0.0378 (14)	−0.0003 (12)	0.0022 (11)	−0.0012 (12)
C3	0.0420 (16)	0.0466 (17)	0.0394 (16)	−0.0026 (14)	0.0008 (12)	−0.0077 (14)
C4	0.0418 (16)	0.0510 (18)	0.0348 (16)	0.0032 (13)	−0.0010 (12)	−0.0006 (14)
C5	0.0477 (16)	0.0373 (16)	0.0366 (15)	−0.0004 (13)	0.0045 (12)	0.0007 (13)
C6	0.0425 (15)	0.0393 (16)	0.0400 (15)	0.0031 (13)	0.0042 (12)	−0.0012 (13)
C7	0.0386 (14)	0.0395 (16)	0.0347 (14)	−0.0009 (12)	0.0027 (12)	−0.0024 (13)
C8	0.0391 (15)	0.0453 (17)	0.0459 (17)	−0.0037 (14)	0.0078 (12)	−0.0055 (15)
C9	0.0491 (18)	0.0473 (18)	0.0562 (19)	0.0028 (15)	−0.0004 (15)	−0.0025 (16)
C10	0.0509 (18)	0.068 (2)	0.0508 (19)	0.0006 (17)	0.0142 (15)	−0.0085 (18)
C11	0.0463 (17)	0.0502 (19)	0.056 (2)	−0.0064 (15)	0.0090 (14)	−0.0006 (16)
C12	0.0388 (15)	0.0354 (15)	0.0359 (15)	0.0021 (12)	0.0076 (11)	0.0010 (12)
C13	0.0455 (16)	0.0323 (15)	0.0343 (14)	−0.0020 (12)	0.0037 (12)	−0.0028 (12)
C14	0.0584 (18)	0.0465 (18)	0.0372 (16)	0.0009 (16)	0.0053 (13)	0.0014 (15)
C15	0.0395 (14)	0.0357 (15)	0.0309 (14)	−0.0003 (13)	−0.0034 (11)	0.0043 (13)
C16	0.0446 (16)	0.0323 (14)	0.0364 (15)	−0.0023 (12)	−0.0039 (12)	0.0015 (12)
C17	0.0400 (14)	0.0367 (15)	0.0343 (14)	−0.0034 (12)	−0.0027 (11)	0.0062 (13)
C18	0.0436 (16)	0.0407 (16)	0.0442 (17)	−0.0060 (13)	−0.0055 (13)	0.0050 (13)
C19	0.0372 (15)	0.0489 (18)	0.0472 (17)	−0.0064 (14)	0.0005 (13)	0.0099 (15)
C20	0.0379 (15)	0.0473 (18)	0.0410 (16)	0.0021 (13)	0.0026 (12)	0.0070 (14)
C21	0.0419 (16)	0.0388 (16)	0.0371 (15)	−0.0002 (13)	0.0007 (12)	−0.0001 (13)
C22	0.0390 (14)	0.0372 (15)	0.0332 (14)	−0.0001 (12)	−0.0025 (11)	0.0022 (12)
C23	0.0402 (15)	0.0346 (15)	0.0394 (15)	−0.0034 (12)	−0.0015 (11)	−0.0006 (13)
C24	0.0356 (13)	0.0381 (15)	0.0382 (15)	−0.0057 (12)	−0.0001 (11)	0.0003 (13)
C25	0.0499 (17)	0.062 (2)	0.0463 (18)	0.0049 (17)	0.0088 (14)	0.0044 (17)

Geometric parameters (Å, º) top

O1—C7	1.417 (3)	C10—H10C	0.9800
O1—C8	1.446 (3)	C11—H11A	0.9800
O2—C12	1.344 (3)	C11—H11B	0.9800
O2—C1	1.459 (3)	C11—H11C	0.9800
O3—C12	1.214 (3)	C12—C13	1.507 (4)
O4—C20	1.365 (3)	C13—C15	1.520 (4)
O4—C25	1.427 (4)	C13—C14	1.535 (4)
C1—C2	1.538 (4)	C13—H13A	1.0000
C1—C6	1.554 (4)	C14—H14A	0.9800
C1—H1A	1.0000	C14—H14B	0.9800
C2—C3	1.513 (4)	C14—H14C	0.9800
C2—C7	1.540 (4)	C15—C16	1.372 (4)
C2—H2A	1.0000	C15—C24	1.419 (4)
C3—C4	1.324 (4)	C16—C17	1.412 (4)
C3—H3	0.9500	C16—H16A	0.9500
C4—C5	1.504 (4)	C17—C22	1.422 (4)
C4—H4	0.9500	C17—C18	1.428 (4)
C5—C7	1.543 (4)	C18—C19	1.363 (4)
C5—C6	1.560 (4)	C18—H18A	0.9500
C5—H5A	1.0000	C19—C20	1.417 (5)
C6—H6A	0.9900	C19—H19A	0.9500
C6—H6B	0.9900	C20—C21	1.371 (4)
C7—H7A	1.0000	C21—C22	1.420 (4)
C8—C10	1.512 (4)	C21—H21A	0.9500
C8—C11	1.518 (5)	C22—C23	1.409 (4)
C8—C9	1.537 (5)	C23—C24	1.367 (4)
C9—H9A	0.9800	C23—H23A	0.9500
C9—H9B	0.9800	C24—H24A	0.9500
C9—H9C	0.9800	C25—H25A	0.9800
C10—H10A	0.9800	C25—H25B	0.9800
C10—H10B	0.9800	C25—H25C	0.9800

C7—O1—C8	116.4 (2)	C8—C11—H11A	109.5
C12—O2—C1	116.9 (2)	C8—C11—H11B	109.5
C20—O4—C25	116.6 (2)	H11A—C11—H11B	109.5
O2—C1—C2	110.2 (2)	C8—C11—H11C	109.5
O2—C1—C6	107.5 (2)	H11A—C11—H11C	109.5
C2—C1—C6	103.7 (2)	H11B—C11—H11C	109.5
O2—C1—H1A	111.7	O3—C12—O2	123.4 (3)
C2—C1—H1A	111.7	O3—C12—C13	124.9 (3)
C6—C1—H1A	111.7	O2—C12—C13	111.7 (2)
C3—C2—C1	106.3 (2)	C12—C13—C15	107.9 (2)
C3—C2—C7	100.5 (2)	C12—C13—C14	110.6 (2)
C1—C2—C7	99.5 (2)	C15—C13—C14	112.2 (2)
C3—C2—H2A	116.0	C12—C13—H13A	108.7
C1—C2—H2A	116.0	C15—C13—H13A	108.7
C7—C2—H2A	116.0	C14—C13—H13A	108.7
C4—C3—C2	107.2 (3)	C13—C14—H14A	109.5
C4—C3—H3	126.4	C13—C14—H14B	109.5
C2—C3—H3	126.4	H14A—C14—H14B	109.5
C3—C4—C5	108.5 (3)	C13—C14—H14C	109.5
C3—C4—H4	125.7	H14A—C14—H14C	109.5
C5—C4—H4	125.7	H14B—C14—H14C	109.5
C4—C5—C7	100.4 (2)	C16—C15—C24	118.7 (3)
C4—C5—C6	106.4 (2)	C16—C15—C13	122.8 (3)
C7—C5—C6	98.9 (2)	C24—C15—C13	118.5 (2)
C4—C5—H5A	116.2	C15—C16—C17	121.6 (3)
C7—C5—H5A	116.2	C15—C16—H16A	119.2
C6—C5—H5A	116.2	C17—C16—H16A	119.2
C1—C6—C5	102.3 (2)	C16—C17—C22	119.1 (2)
C1—C6—H6A	111.3	C16—C17—C18	122.8 (3)
C5—C6—H6A	111.3	C22—C17—C18	118.1 (3)
C1—C6—H6B	111.3	C19—C18—C17	121.0 (3)
C5—C6—H6B	111.3	C19—C18—H18A	119.5
H6A—C6—H6B	109.2	C17—C18—H18A	119.5
O1—C7—C2	113.1 (2)	C18—C19—C20	120.7 (3)
O1—C7—C5	115.4 (2)	C18—C19—H19A	119.6
C2—C7—C5	93.8 (2)	C20—C19—H19A	119.6
O1—C7—H7A	111.2	O4—C20—C21	125.0 (3)
C2—C7—H7A	111.2	O4—C20—C19	115.3 (3)
C5—C7—H7A	111.2	C21—C20—C19	119.7 (3)
O1—C8—C10	103.8 (2)	C20—C21—C22	120.8 (3)
O1—C8—C11	110.9 (3)	C20—C21—H21A	119.6
C10—C8—C11	110.8 (3)	C22—C21—H21A	119.6
O1—C8—C9	109.5 (3)	C23—C22—C21	122.0 (3)
C10—C8—C9	110.1 (3)	C23—C22—C17	118.5 (2)
C11—C8—C9	111.4 (3)	C21—C22—C17	119.4 (2)
C8—C9—H9A	109.5	C24—C23—C22	121.1 (3)
C8—C9—H9B	109.5	C24—C23—H23A	119.5
H9A—C9—H9B	109.5	C22—C23—H23A	119.5
C8—C9—H9C	109.5	C23—C24—C15	120.9 (2)
H9A—C9—H9C	109.5	C23—C24—H24A	119.6
H9B—C9—H9C	109.5	C15—C24—H24A	119.6
C8—C10—H10A	109.5	O4—C25—H25A	109.5
C8—C10—H10B	109.5	O4—C25—H25B	109.5
H10A—C10—H10B	109.5	H25A—C25—H25B	109.5
C8—C10—H10C	109.5	O4—C25—H25C	109.5
H10A—C10—H10C	109.5	H25A—C25—H25C	109.5
H10B—C10—H10C	109.5	H25B—C25—H25C	109.5

Experimental details

Crystal data
Chemical formula	C₂₅H₃₀O₄
M_r	394.49
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	150
a, b, c (Å)	11.8328 (11), 6.0084 (4), 15.2205 (15)
β (°)	96.705 (4)
V (Å³)	1074.72 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.20 × 0.12

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.480, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	8333, 2649, 2023
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.122, 1.05
No. of reflections	2649
No. of parameters	267
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.25

Computer programs: COLLECT (Nonius, 2002), DENZO-SMN (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Acknowledgements

The authors wish to acknowledge NSERC Canada and the University of Toronto for funding.

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
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