Tetra-tert-butyl 13,14-dioxapenta­cyclo­[8.2.1.14,7.02,9.03,8]tetra­deca-5,11-diene-5,6,11,12-tetra­carboxyl­ate

Lough, A.J.; Jack, K.; Tam, W.

doi:10.1107/S1600536812039220

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o2962

https://doi.org/10.1107/S1600536812039220

Open

access

Tetra-tert-butyl 13,14-dioxapentacyclo[8.2.1.1^4,7.0^2,9.0^3,8]tetradeca-5,11-diene-5,6,11,12-tetracarboxylate

Alan J. Lough,^a ^* Kelsey Jack ^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 3 September 2012; accepted 13 September 2012; online 22 September 2012)

The stereochemistry of the title compound, C₃₂H₄₄O₁₀, at the cyclobutane ring is cis-anti-cis. The molecule lies across an inversion center. In the crystal, weak C—H⋯O hydrogen bonds connect molecules into chains along [100], forming R₂²(6) rings.

Related literature

For related structures, see: Lough et al. (2012a ,b ). For the synthetic background, see: Ballantine et al. (2009 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₃₂H₄₄O₁₀
M_r = 588.67
Triclinic, $[P \overline 1]$
a = 5.8376 (10) Å
b = 9.4895 (17) Å
c = 14.924 (3) Å
α = 99.926 (4)°
β = 98.545 (4)°
γ = 100.462 (4)°
V = 786.9 (2) Å³
Z = 1
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 150 K
0.45 × 0.25 × 0.15 mm

Data collection

Bruker Kappa APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.698, T_max = 0.746
6490 measured reflections
3559 independent reflections
3024 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.104
S = 1.04
3559 reflections
196 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O1ⁱ	1.00	2.47	3.2118 (16)	130
Symmetry code: (i) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812039220/hb6953sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039220/hb6953Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812039220/hb6953Isup3.cml

checkCIF report

Comment top

We have recently investigated the Ru-catalyzed isomerization and dimerization reaction of oxanorbornadiene compounds (Ballantine et al., 2009). When dissolved in 1,2-dichloroethane in the presence of Cp*Ru(COD)Cl, tert-butoxy-7-oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylate will dimerize into the title compound (I) (see Fig. 1). The desired product was resolved using fractional crystallization in hexanes. The stereochemistry of the product was determined by this single-crystal X-ray analysis and was found to have a cis-anti-cis stereochemistry at the cyclobutane ring of the dimer.

The molecular structure of (I) is shown in Fig. 2. In the crystal, weak C—H···O hydrogen bonds connect molecules into one-dimensional chains (Fig. 3) along [100] forming R²₂(6) rings (Bernstein et al., 1995).

For related structures see the preceding (Lough et al., 2012a) and following (Lough et al., 2012b) papers

Related literature top

For related structures, see: Lough et al. (2012a,b). For the synthetic background, see: Ballantine et al. (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

tert-Butoxy-7-oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylate 1 (45 mg, 0.15 mmol) was weighed into an oven-dried vial, purged with nitrogen and transferred into a Dry Box. In the Dry Box, Cp*Ru(COD)Cl (10 mol%) was added to another oven dried vial and dissolved in 1,2-dichloroethane (0.5 ml). The Ru-catalyst was then transferred into the vial containing the 7-oxanorbornadiene. The vial was sealed with a screw cap and removed from the Dry Box. The reaction was heated at 333 K with stirring for 20 h. The crude product was purified by column chromatography (EtOAc:hexanes = 2:3) followed by recrystallization in hexanes to give the dimer (I). Colourless blocks were grown by slow evaportation of a solution of (I) in hexanes.

Structure description top

For related structures see the preceding (Lough et al., 2012a) and following (Lough et al., 2012b) papers

For related structures, see: Lough et al. (2012a,b). For the synthetic background, see: Ballantine et al. (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Reaction scheme
	Fig. 2. The molecular structure of (I) showing 30% probability ellipsoids (symmetry code (a): -x + 1, -y + 1, -z).
	Fig. 3. Part of the crystal structure showing weak hydrogen bonds as dashed lines.

Tetra-tert-butyl 13,14-dioxapentacyclo[8.2.1.1^4,7.0^2,9.0^3,8]tetradeca- 5,11-diene-5,6,11,12-tetracarboxylate top

Crystal data top

C₃₂H₄₄O₁₀	Z = 1
M_r = 588.67	F(000) = 316
Triclinic, P1	D_x = 1.242 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8376 (10) Å	Cell parameters from 4249 reflections
b = 9.4895 (17) Å	θ = 2.2–27.5°
c = 14.924 (3) Å	µ = 0.09 mm⁻¹
α = 99.926 (4)°	T = 150 K
β = 98.545 (4)°	Block, colourless
γ = 100.462 (4)°	0.45 × 0.25 × 0.15 mm
V = 786.9 (2) Å³

Data collection top

Bruker Kappa APEX DUO CCD diffractometer	3559 independent reflections
Radiation source: fine-focus sealed tube	3024 reflections with I > 2σ(I)
Bruker Triumph monochromator	R_int = 0.015
φ and ω scans	θ_max = 27.5°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −7→4
T_min = 0.698, T_max = 0.746	k = −12→12
6490 measured reflections	l = −19→18

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0475P)² + 0.3125P] where P = (F_o² + 2F_c²)/3
3559 reflections	(Δ/σ)_max = 0.001
196 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₃₂H₄₄O₁₀	γ = 100.462 (4)°
M_r = 588.67	V = 786.9 (2) Å³
Triclinic, P1	Z = 1
a = 5.8376 (10) Å	Mo Kα radiation
b = 9.4895 (17) Å	µ = 0.09 mm⁻¹
c = 14.924 (3) Å	T = 150 K
α = 99.926 (4)°	0.45 × 0.25 × 0.15 mm
β = 98.545 (4)°

Data collection top

Bruker Kappa APEX DUO CCD diffractometer	3559 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	3024 reflections with I > 2σ(I)
T_min = 0.698, T_max = 0.746	R_int = 0.015
6490 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.04	Δρ_max = 0.33 e Å⁻³
3559 reflections	Δρ_min = −0.21 e Å⁻³
196 parameters

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 > 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	0.22773 (14)	0.65121 (9)	0.02699 (6)	0.01803 (19)
O2	0.35940 (19)	0.52069 (10)	0.29004 (7)	0.0282 (2)
O3	0.26592 (16)	0.74251 (10)	0.32725 (6)	0.0217 (2)
O4	0.68115 (18)	0.95566 (11)	0.29352 (7)	0.0298 (2)
O5	0.80759 (16)	0.97519 (9)	0.15871 (6)	0.0207 (2)
C1	0.3636 (2)	0.67330 (13)	0.18207 (8)	0.0174 (2)
C2	0.2523 (2)	0.55902 (13)	0.09395 (8)	0.0165 (2)
H2A	0.1029	0.4910	0.0973	0.020*
C3	0.4520 (2)	0.48426 (13)	0.06656 (8)	0.0154 (2)
H3	0.5361	0.4416	0.1152	0.018*
C4	0.6083 (2)	0.61021 (12)	0.03288 (8)	0.0146 (2)
H4	0.7801	0.6364	0.0622	0.018*
C5	0.4701 (2)	0.73280 (13)	0.05005 (8)	0.0164 (2)
H5A	0.5070	0.8137	0.0160	0.020*
C6	0.5012 (2)	0.78123 (13)	0.15483 (8)	0.0167 (2)
C7	0.3337 (2)	0.63815 (13)	0.27330 (8)	0.0180 (2)
C8	0.2067 (2)	0.72280 (14)	0.41859 (8)	0.0211 (3)
C9	0.4200 (3)	0.69922 (18)	0.48118 (10)	0.0332 (3)
H9A	0.5579	0.7767	0.4830	0.050*
H9B	0.4535	0.6038	0.4572	0.050*
H9C	0.3865	0.7020	0.5438	0.050*
C10	0.1460 (3)	0.86826 (18)	0.45469 (11)	0.0375 (4)
H10A	0.0047	0.8794	0.4143	0.056*
H10B	0.2793	0.9481	0.4555	0.056*
H10C	0.1146	0.8712	0.5176	0.056*
C11	−0.0074 (3)	0.59823 (18)	0.40294 (11)	0.0347 (3)
H11A	−0.1297	0.6103	0.3540	0.052*
H11B	−0.0703	0.5989	0.4603	0.052*
H11C	0.0392	0.5049	0.3844	0.052*
C12	0.6722 (2)	0.91271 (13)	0.21227 (8)	0.0169 (2)
C13	0.9780 (2)	1.11711 (14)	0.19571 (9)	0.0212 (3)
C14	0.8388 (3)	1.23483 (16)	0.21650 (13)	0.0371 (4)
H14A	0.7595	1.2190	0.2685	0.056*
H14B	0.7199	1.2307	0.1618	0.056*
H14C	0.9469	1.3311	0.2327	0.056*
C15	1.1022 (3)	1.13826 (18)	0.11508 (11)	0.0380 (4)
H15A	0.9856	1.1420	0.0615	0.057*
H15B	1.1795	1.0563	0.0992	0.057*
H15C	1.2216	1.2301	0.1325	0.057*
C16	1.1550 (3)	1.10905 (18)	0.27928 (11)	0.0344 (4)
H16A	1.0756	1.1054	0.3325	0.052*
H16B	1.2846	1.1957	0.2937	0.052*
H16C	1.2190	1.0208	0.2655	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0147 (4)	0.0190 (4)	0.0187 (4)	0.0016 (3)	0.0010 (3)	0.0033 (3)
O2	0.0417 (6)	0.0206 (5)	0.0259 (5)	0.0099 (4)	0.0126 (4)	0.0059 (4)
O3	0.0300 (5)	0.0195 (4)	0.0184 (4)	0.0067 (4)	0.0118 (4)	0.0039 (3)
O4	0.0303 (5)	0.0322 (6)	0.0183 (5)	−0.0081 (4)	0.0071 (4)	−0.0046 (4)
O5	0.0246 (5)	0.0151 (4)	0.0186 (4)	−0.0039 (3)	0.0061 (3)	0.0003 (3)
C1	0.0169 (6)	0.0167 (6)	0.0176 (6)	0.0030 (4)	0.0048 (4)	0.0004 (4)
C2	0.0154 (6)	0.0167 (6)	0.0158 (6)	−0.0001 (4)	0.0041 (4)	0.0018 (4)
C3	0.0157 (6)	0.0141 (5)	0.0145 (6)	−0.0005 (4)	0.0035 (4)	0.0009 (4)
C4	0.0137 (5)	0.0144 (6)	0.0139 (5)	−0.0002 (4)	0.0029 (4)	0.0009 (4)
C5	0.0160 (6)	0.0155 (6)	0.0160 (6)	0.0004 (4)	0.0025 (4)	0.0017 (4)
C6	0.0169 (6)	0.0159 (6)	0.0166 (6)	0.0036 (4)	0.0045 (4)	0.0005 (4)
C7	0.0159 (6)	0.0175 (6)	0.0181 (6)	−0.0006 (4)	0.0046 (4)	0.0000 (4)
C8	0.0267 (7)	0.0247 (7)	0.0144 (6)	0.0071 (5)	0.0088 (5)	0.0045 (5)
C9	0.0363 (8)	0.0394 (8)	0.0230 (7)	0.0129 (6)	0.0008 (6)	0.0028 (6)
C10	0.0595 (11)	0.0365 (9)	0.0257 (8)	0.0253 (8)	0.0185 (7)	0.0062 (6)
C11	0.0293 (8)	0.0438 (9)	0.0320 (8)	0.0004 (6)	0.0146 (6)	0.0107 (7)
C12	0.0168 (6)	0.0155 (6)	0.0179 (6)	0.0024 (4)	0.0043 (4)	0.0022 (4)
C13	0.0200 (6)	0.0161 (6)	0.0227 (6)	−0.0052 (5)	0.0013 (5)	0.0031 (5)
C14	0.0375 (9)	0.0171 (7)	0.0513 (10)	0.0022 (6)	0.0024 (7)	0.0016 (6)
C15	0.0415 (9)	0.0357 (8)	0.0305 (8)	−0.0128 (7)	0.0109 (6)	0.0080 (6)
C16	0.0213 (7)	0.0430 (9)	0.0339 (8)	−0.0044 (6)	−0.0031 (6)	0.0137 (7)

Geometric parameters (Å, º) top

O1—C5	1.4442 (14)	C8—C10	1.5164 (19)
O1—C2	1.4453 (14)	C8—C9	1.5171 (19)
O2—C7	1.2135 (16)	C9—H9A	0.9800
O3—C7	1.3220 (15)	C9—H9B	0.9800
O3—C8	1.4892 (15)	C9—H9C	0.9800
O4—C12	1.2010 (16)	C10—H10A	0.9800
O5—C12	1.3402 (15)	C10—H10B	0.9800
O5—C13	1.4840 (14)	C10—H10C	0.9800
C1—C6	1.3421 (17)	C11—H11A	0.9800
C1—C7	1.4839 (17)	C11—H11B	0.9800
C1—C2	1.5253 (16)	C11—H11C	0.9800
C2—C3	1.5401 (16)	C13—C14	1.513 (2)
C2—H2A	1.0000	C13—C15	1.518 (2)
C3—C4ⁱ	1.5498 (16)	C13—C16	1.5190 (18)
C3—C4	1.5686 (16)	C14—H14A	0.9800
C3—H3	1.0000	C14—H14B	0.9800
C4—C5	1.5392 (16)	C14—H14C	0.9800
C4—C3ⁱ	1.5498 (16)	C15—H15A	0.9800
C4—H4	1.0000	C15—H15B	0.9800
C5—C6	1.5255 (16)	C15—H15C	0.9800
C5—H5A	1.0000	C16—H16A	0.9800
C6—C12	1.4876 (16)	C16—H16B	0.9800
C8—C11	1.515 (2)	C16—H16C	0.9800

C5—O1—C2	96.18 (8)	H9A—C9—H9B	109.5
C7—O3—C8	120.96 (10)	C8—C9—H9C	109.5
C12—O5—C13	121.03 (10)	H9A—C9—H9C	109.5
C6—C1—C7	134.31 (11)	H9B—C9—H9C	109.5
C6—C1—C2	105.44 (10)	C8—C10—H10A	109.5
C7—C1—C2	119.46 (10)	C8—C10—H10B	109.5
O1—C2—C1	101.00 (9)	H10A—C10—H10B	109.5
O1—C2—C3	102.44 (9)	C8—C10—H10C	109.5
C1—C2—C3	105.96 (9)	H10A—C10—H10C	109.5
O1—C2—H2A	115.2	H10B—C10—H10C	109.5
C1—C2—H2A	115.2	C8—C11—H11A	109.5
C3—C2—H2A	115.2	C8—C11—H11B	109.5
C2—C3—C4ⁱ	113.90 (9)	H11A—C11—H11B	109.5
C2—C3—C4	100.76 (9)	C8—C11—H11C	109.5
C4ⁱ—C3—C4	90.45 (9)	H11A—C11—H11C	109.5
C2—C3—H3	116.0	H11B—C11—H11C	109.5
C4ⁱ—C3—H3	116.0	O4—C12—O5	126.38 (11)
C4—C3—H3	116.0	O4—C12—C6	124.31 (11)
C5—C4—C3ⁱ	115.39 (9)	O5—C12—C6	109.30 (10)
C5—C4—C3	101.01 (9)	O5—C13—C14	108.34 (11)
C3ⁱ—C4—C3	89.55 (9)	O5—C13—C15	102.62 (10)
C5—C4—H4	115.7	C14—C13—C15	110.74 (13)
C3ⁱ—C4—H4	115.7	O5—C13—C16	111.42 (11)
C3—C4—H4	115.7	C14—C13—C16	112.83 (13)
O1—C5—C6	101.33 (9)	C15—C13—C16	110.40 (12)
O1—C5—C4	101.79 (9)	C13—C14—H14A	109.5
C6—C5—C4	106.44 (9)	C13—C14—H14B	109.5
O1—C5—H5A	115.2	H14A—C14—H14B	109.5
C6—C5—H5A	115.2	C13—C14—H14C	109.5
C4—C5—H5A	115.2	H14A—C14—H14C	109.5
C1—C6—C12	129.04 (11)	H14B—C14—H14C	109.5
C1—C6—C5	105.29 (10)	C13—C15—H15A	109.5
C12—C6—C5	125.30 (11)	C13—C15—H15B	109.5
O2—C7—O3	126.77 (12)	H15A—C15—H15B	109.5
O2—C7—C1	120.41 (11)	C13—C15—H15C	109.5
O3—C7—C1	112.71 (10)	H15A—C15—H15C	109.5
O3—C8—C11	108.87 (10)	H15B—C15—H15C	109.5
O3—C8—C10	101.91 (10)	C13—C16—H16A	109.5
C11—C8—C10	111.03 (12)	C13—C16—H16B	109.5
O3—C8—C9	110.50 (11)	H16A—C16—H16B	109.5
C11—C8—C9	112.93 (12)	C13—C16—H16C	109.5
C10—C8—C9	111.03 (12)	H16A—C16—H16C	109.5
C8—C9—H9A	109.5	H16B—C16—H16C	109.5
C8—C9—H9B	109.5

C5—O1—C2—C1	51.53 (10)	C2—C1—C6—C5	0.72 (12)
C5—O1—C2—C3	−57.73 (10)	O1—C5—C6—C1	32.18 (12)
C6—C1—C2—O1	−33.35 (12)	C4—C5—C6—C1	−73.86 (12)
C7—C1—C2—O1	155.41 (10)	O1—C5—C6—C12	−154.29 (11)
C6—C1—C2—C3	73.14 (12)	C4—C5—C6—C12	99.66 (13)
C7—C1—C2—C3	−98.11 (12)	C8—O3—C7—O2	−1.27 (19)
O1—C2—C3—C4ⁱ	−61.22 (11)	C8—O3—C7—C1	174.85 (10)
C1—C2—C3—C4ⁱ	−166.66 (9)	C6—C1—C7—O2	−123.53 (16)
O1—C2—C3—C4	34.11 (10)	C2—C1—C7—O2	44.64 (17)
C1—C2—C3—C4	−71.33 (11)	C6—C1—C7—O3	60.08 (18)
C2—C3—C4—C5	1.36 (10)	C2—C1—C7—O3	−131.75 (11)
C4ⁱ—C3—C4—C5	115.81 (10)	C7—O3—C8—C11	−63.78 (15)
C2—C3—C4—C3ⁱ	−114.45 (10)	C7—O3—C8—C10	178.84 (12)
C4ⁱ—C3—C4—C3ⁱ	0.0	C7—O3—C8—C9	60.78 (15)
C2—O1—C5—C6	−51.21 (10)	C13—O5—C12—O4	−4.86 (19)
C2—O1—C5—C4	58.47 (10)	C13—O5—C12—C6	173.80 (10)
C3ⁱ—C4—C5—O1	58.36 (12)	C1—C6—C12—O4	−14.3 (2)
C3—C4—C5—O1	−36.43 (10)	C5—C6—C12—O4	173.77 (12)
C3ⁱ—C4—C5—C6	164.08 (10)	C1—C6—C12—O5	167.03 (12)
C3—C4—C5—C6	69.28 (11)	C5—C6—C12—O5	−4.92 (16)
C7—C1—C6—C12	−3.2 (2)	C12—O5—C13—C14	−67.15 (15)
C2—C1—C6—C12	−172.48 (11)	C12—O5—C13—C15	175.69 (12)
C7—C1—C6—C5	170.05 (13)	C12—O5—C13—C16	57.55 (16)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1ⁱⁱ	1.00	2.47	3.2118 (16)	130

Symmetry code: (ii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₃₂H₄₄O₁₀
M_r	588.67
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	5.8376 (10), 9.4895 (17), 14.924 (3)
α, β, γ (°)	99.926 (4), 98.545 (4), 100.462 (4)
V (Å³)	786.9 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.45 × 0.25 × 0.15

Data collection
Diffractometer	Bruker Kappa APEX DUO CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.698, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	6490, 3559, 3024
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.104, 1.04
No. of reflections	3559
No. of parameters	196
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.21

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1ⁱ	1.00	2.47	3.2118 (16)	130

Symmetry code: (i) −x, −y+1, −z.

Acknowledgements

The University of Toronto thanks NSERC Canada for funding.

References

Ballantine, M., Menard, M. L. & Tam, W. (2009). J. Org. Chem. 74, 7570–7573. Web of Science CrossRef PubMed CAS Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lough, A. J., Jack, K. & Tam, W. (2012a). Acta Cryst. E68, o2961. CSD CrossRef IUCr Journals Google Scholar
Lough, A. J., Jack, K. & Tam, W. (2012b). Acta Cryst. E68, o2963. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o2962

https://doi.org/10.1107/S1600536812039220

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Tetra-tert-butyl 13,14-dioxa­penta­cyclo­[8.2.1.14,7.02,9.03,8]tetra­deca-5,11-diene-5,6,11,12-tetra­carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Tetra-tert-butyl 13,14-dioxapentacyclo[8.2.1.1^4,7.0^2,9.0^3,8]tetradeca-5,11-diene-5,6,11,12-tetracarboxylate