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ISSN: 2056-9890

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

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[Lough, A. J., Jack, K. & Tam, W. (2012a). Acta Cryst. E68, o2961.],b[Lough, A. J., Jack, K. & Tam, W. (2012b). Acta Cryst. E68, o2963.]). For the synthetic background, see: Ballantine et al. (2009[Ballantine, M., Menard, M. L. & Tam, W. (2009). J. Org. Chem. 74, 7570-7573.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C32H44O10

  • Mr = 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[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.698, Tmax = 0.746

  • 6490 measured reflections

  • 3559 independent reflections

  • 3024 reflections with I > 2σ(I)

  • Rint = 0.015

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.104

  • S = 1.04

  • 3559 reflections

  • 196 parameters

  • H-atom parameters constrained

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


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.

Refinement top

Hydrogen atoms were placed in calculated positions with C—H distances of 0.98 and 1.00 Å. They were included in the refinement in a riding-model approximation with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl).

Structure description 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

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
[Figure 1] Fig. 1. Reaction scheme
[Figure 2] Fig. 2. The molecular structure of (I) showing 30% probability ellipsoids (symmetry code (a): -x + 1, -y + 1, -z).
[Figure 3] Fig. 3. Part of the crystal structure showing weak hydrogen bonds as dashed lines.
Tetra-tert-butyl 13,14-dioxapentacyclo[8.2.1.14,7.02,9.03,8]tetradeca- 5,11-diene-5,6,11,12-tetracarboxylate top
Crystal data top
C32H44O10Z = 1
Mr = 588.67F(000) = 316
Triclinic, P1Dx = 1.242 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.8376 (10) ÅCell parameters from 4249 reflections
b = 9.4895 (17) Åθ = 2.2–27.5°
c = 14.924 (3) ŵ = 0.09 mm1
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 tube3024 reflections with I > 2σ(I)
Bruker Triumph monochromatorRint = 0.015
φ and ω scansθmax = 27.5°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 74
Tmin = 0.698, Tmax = 0.746k = 1212
6490 measured reflectionsl = 1918
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0475P)2 + 0.3125P]
where P = (Fo2 + 2Fc2)/3
3559 reflections(Δ/σ)max = 0.001
196 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C32H44O10γ = 100.462 (4)°
Mr = 588.67V = 786.9 (2) Å3
Triclinic, P1Z = 1
a = 5.8376 (10) ÅMo Kα radiation
b = 9.4895 (17) ŵ = 0.09 mm1
c = 14.924 (3) ÅT = 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)
Tmin = 0.698, Tmax = 0.746Rint = 0.015
6490 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.104H-atom parameters constrained
S = 1.04Δρmax = 0.33 e Å3
3559 reflectionsΔρmin = 0.21 e Å3
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
xyzUiso*/Ueq
O10.22773 (14)0.65121 (9)0.02699 (6)0.01803 (19)
O20.35940 (19)0.52069 (10)0.29004 (7)0.0282 (2)
O30.26592 (16)0.74251 (10)0.32725 (6)0.0217 (2)
O40.68115 (18)0.95566 (11)0.29352 (7)0.0298 (2)
O50.80759 (16)0.97519 (9)0.15871 (6)0.0207 (2)
C10.3636 (2)0.67330 (13)0.18207 (8)0.0174 (2)
C20.2523 (2)0.55902 (13)0.09395 (8)0.0165 (2)
H2A0.10290.49100.09730.020*
C30.4520 (2)0.48426 (13)0.06656 (8)0.0154 (2)
H30.53610.44160.11520.018*
C40.6083 (2)0.61021 (12)0.03288 (8)0.0146 (2)
H40.78010.63640.06220.018*
C50.4701 (2)0.73280 (13)0.05005 (8)0.0164 (2)
H5A0.50700.81370.01600.020*
C60.5012 (2)0.78123 (13)0.15483 (8)0.0167 (2)
C70.3337 (2)0.63815 (13)0.27330 (8)0.0180 (2)
C80.2067 (2)0.72280 (14)0.41859 (8)0.0211 (3)
C90.4200 (3)0.69922 (18)0.48118 (10)0.0332 (3)
H9A0.55790.77670.48300.050*
H9B0.45350.60380.45720.050*
H9C0.38650.70200.54380.050*
C100.1460 (3)0.86826 (18)0.45469 (11)0.0375 (4)
H10A0.00470.87940.41430.056*
H10B0.27930.94810.45550.056*
H10C0.11460.87120.51760.056*
C110.0074 (3)0.59823 (18)0.40294 (11)0.0347 (3)
H11A0.12970.61030.35400.052*
H11B0.07030.59890.46030.052*
H11C0.03920.50490.38440.052*
C120.6722 (2)0.91271 (13)0.21227 (8)0.0169 (2)
C130.9780 (2)1.11711 (14)0.19571 (9)0.0212 (3)
C140.8388 (3)1.23483 (16)0.21650 (13)0.0371 (4)
H14A0.75951.21900.26850.056*
H14B0.71991.23070.16180.056*
H14C0.94691.33110.23270.056*
C151.1022 (3)1.13826 (18)0.11508 (11)0.0380 (4)
H15A0.98561.14200.06150.057*
H15B1.17951.05630.09920.057*
H15C1.22161.23010.13250.057*
C161.1550 (3)1.10905 (18)0.27928 (11)0.0344 (4)
H16A1.07561.10540.33250.052*
H16B1.28461.19570.29370.052*
H16C1.21901.02080.26550.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0147 (4)0.0190 (4)0.0187 (4)0.0016 (3)0.0010 (3)0.0033 (3)
O20.0417 (6)0.0206 (5)0.0259 (5)0.0099 (4)0.0126 (4)0.0059 (4)
O30.0300 (5)0.0195 (4)0.0184 (4)0.0067 (4)0.0118 (4)0.0039 (3)
O40.0303 (5)0.0322 (6)0.0183 (5)0.0081 (4)0.0071 (4)0.0046 (4)
O50.0246 (5)0.0151 (4)0.0186 (4)0.0039 (3)0.0061 (3)0.0003 (3)
C10.0169 (6)0.0167 (6)0.0176 (6)0.0030 (4)0.0048 (4)0.0004 (4)
C20.0154 (6)0.0167 (6)0.0158 (6)0.0001 (4)0.0041 (4)0.0018 (4)
C30.0157 (6)0.0141 (5)0.0145 (6)0.0005 (4)0.0035 (4)0.0009 (4)
C40.0137 (5)0.0144 (6)0.0139 (5)0.0002 (4)0.0029 (4)0.0009 (4)
C50.0160 (6)0.0155 (6)0.0160 (6)0.0004 (4)0.0025 (4)0.0017 (4)
C60.0169 (6)0.0159 (6)0.0166 (6)0.0036 (4)0.0045 (4)0.0005 (4)
C70.0159 (6)0.0175 (6)0.0181 (6)0.0006 (4)0.0046 (4)0.0000 (4)
C80.0267 (7)0.0247 (7)0.0144 (6)0.0071 (5)0.0088 (5)0.0045 (5)
C90.0363 (8)0.0394 (8)0.0230 (7)0.0129 (6)0.0008 (6)0.0028 (6)
C100.0595 (11)0.0365 (9)0.0257 (8)0.0253 (8)0.0185 (7)0.0062 (6)
C110.0293 (8)0.0438 (9)0.0320 (8)0.0004 (6)0.0146 (6)0.0107 (7)
C120.0168 (6)0.0155 (6)0.0179 (6)0.0024 (4)0.0043 (4)0.0022 (4)
C130.0200 (6)0.0161 (6)0.0227 (6)0.0052 (5)0.0013 (5)0.0031 (5)
C140.0375 (9)0.0171 (7)0.0513 (10)0.0022 (6)0.0024 (7)0.0016 (6)
C150.0415 (9)0.0357 (8)0.0305 (8)0.0128 (7)0.0109 (6)0.0080 (6)
C160.0213 (7)0.0430 (9)0.0339 (8)0.0044 (6)0.0031 (6)0.0137 (7)
Geometric parameters (Å, º) top
O1—C51.4442 (14)C8—C101.5164 (19)
O1—C21.4453 (14)C8—C91.5171 (19)
O2—C71.2135 (16)C9—H9A0.9800
O3—C71.3220 (15)C9—H9B0.9800
O3—C81.4892 (15)C9—H9C0.9800
O4—C121.2010 (16)C10—H10A0.9800
O5—C121.3402 (15)C10—H10B0.9800
O5—C131.4840 (14)C10—H10C0.9800
C1—C61.3421 (17)C11—H11A0.9800
C1—C71.4839 (17)C11—H11B0.9800
C1—C21.5253 (16)C11—H11C0.9800
C2—C31.5401 (16)C13—C141.513 (2)
C2—H2A1.0000C13—C151.518 (2)
C3—C4i1.5498 (16)C13—C161.5190 (18)
C3—C41.5686 (16)C14—H14A0.9800
C3—H31.0000C14—H14B0.9800
C4—C51.5392 (16)C14—H14C0.9800
C4—C3i1.5498 (16)C15—H15A0.9800
C4—H41.0000C15—H15B0.9800
C5—C61.5255 (16)C15—H15C0.9800
C5—H5A1.0000C16—H16A0.9800
C6—C121.4876 (16)C16—H16B0.9800
C8—C111.515 (2)C16—H16C0.9800
C5—O1—C296.18 (8)H9A—C9—H9B109.5
C7—O3—C8120.96 (10)C8—C9—H9C109.5
C12—O5—C13121.03 (10)H9A—C9—H9C109.5
C6—C1—C7134.31 (11)H9B—C9—H9C109.5
C6—C1—C2105.44 (10)C8—C10—H10A109.5
C7—C1—C2119.46 (10)C8—C10—H10B109.5
O1—C2—C1101.00 (9)H10A—C10—H10B109.5
O1—C2—C3102.44 (9)C8—C10—H10C109.5
C1—C2—C3105.96 (9)H10A—C10—H10C109.5
O1—C2—H2A115.2H10B—C10—H10C109.5
C1—C2—H2A115.2C8—C11—H11A109.5
C3—C2—H2A115.2C8—C11—H11B109.5
C2—C3—C4i113.90 (9)H11A—C11—H11B109.5
C2—C3—C4100.76 (9)C8—C11—H11C109.5
C4i—C3—C490.45 (9)H11A—C11—H11C109.5
C2—C3—H3116.0H11B—C11—H11C109.5
C4i—C3—H3116.0O4—C12—O5126.38 (11)
C4—C3—H3116.0O4—C12—C6124.31 (11)
C5—C4—C3i115.39 (9)O5—C12—C6109.30 (10)
C5—C4—C3101.01 (9)O5—C13—C14108.34 (11)
C3i—C4—C389.55 (9)O5—C13—C15102.62 (10)
C5—C4—H4115.7C14—C13—C15110.74 (13)
C3i—C4—H4115.7O5—C13—C16111.42 (11)
C3—C4—H4115.7C14—C13—C16112.83 (13)
O1—C5—C6101.33 (9)C15—C13—C16110.40 (12)
O1—C5—C4101.79 (9)C13—C14—H14A109.5
C6—C5—C4106.44 (9)C13—C14—H14B109.5
O1—C5—H5A115.2H14A—C14—H14B109.5
C6—C5—H5A115.2C13—C14—H14C109.5
C4—C5—H5A115.2H14A—C14—H14C109.5
C1—C6—C12129.04 (11)H14B—C14—H14C109.5
C1—C6—C5105.29 (10)C13—C15—H15A109.5
C12—C6—C5125.30 (11)C13—C15—H15B109.5
O2—C7—O3126.77 (12)H15A—C15—H15B109.5
O2—C7—C1120.41 (11)C13—C15—H15C109.5
O3—C7—C1112.71 (10)H15A—C15—H15C109.5
O3—C8—C11108.87 (10)H15B—C15—H15C109.5
O3—C8—C10101.91 (10)C13—C16—H16A109.5
C11—C8—C10111.03 (12)C13—C16—H16B109.5
O3—C8—C9110.50 (11)H16A—C16—H16B109.5
C11—C8—C9112.93 (12)C13—C16—H16C109.5
C10—C8—C9111.03 (12)H16A—C16—H16C109.5
C8—C9—H9A109.5H16B—C16—H16C109.5
C8—C9—H9B109.5
C5—O1—C2—C151.53 (10)C2—C1—C6—C50.72 (12)
C5—O1—C2—C357.73 (10)O1—C5—C6—C132.18 (12)
C6—C1—C2—O133.35 (12)C4—C5—C6—C173.86 (12)
C7—C1—C2—O1155.41 (10)O1—C5—C6—C12154.29 (11)
C6—C1—C2—C373.14 (12)C4—C5—C6—C1299.66 (13)
C7—C1—C2—C398.11 (12)C8—O3—C7—O21.27 (19)
O1—C2—C3—C4i61.22 (11)C8—O3—C7—C1174.85 (10)
C1—C2—C3—C4i166.66 (9)C6—C1—C7—O2123.53 (16)
O1—C2—C3—C434.11 (10)C2—C1—C7—O244.64 (17)
C1—C2—C3—C471.33 (11)C6—C1—C7—O360.08 (18)
C2—C3—C4—C51.36 (10)C2—C1—C7—O3131.75 (11)
C4i—C3—C4—C5115.81 (10)C7—O3—C8—C1163.78 (15)
C2—C3—C4—C3i114.45 (10)C7—O3—C8—C10178.84 (12)
C4i—C3—C4—C3i0.0C7—O3—C8—C960.78 (15)
C2—O1—C5—C651.21 (10)C13—O5—C12—O44.86 (19)
C2—O1—C5—C458.47 (10)C13—O5—C12—C6173.80 (10)
C3i—C4—C5—O158.36 (12)C1—C6—C12—O414.3 (2)
C3—C4—C5—O136.43 (10)C5—C6—C12—O4173.77 (12)
C3i—C4—C5—C6164.08 (10)C1—C6—C12—O5167.03 (12)
C3—C4—C5—C669.28 (11)C5—C6—C12—O54.92 (16)
C7—C1—C6—C123.2 (2)C12—O5—C13—C1467.15 (15)
C2—C1—C6—C12172.48 (11)C12—O5—C13—C15175.69 (12)
C7—C1—C6—C5170.05 (13)C12—O5—C13—C1657.55 (16)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O1ii1.002.473.2118 (16)130
Symmetry code: (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC32H44O10
Mr588.67
Crystal system, space groupTriclinic, 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)
V3)786.9 (2)
Z1
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.45 × 0.25 × 0.15
Data collection
DiffractometerBruker Kappa APEX DUO CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.698, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
6490, 3559, 3024
Rint0.015
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.104, 1.04
No. of reflections3559
No. of parameters196
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C2—H2A···O1i1.002.473.2118 (16)130
Symmetry code: (i) x, y+1, z.
 

Acknowledgements

The University of Toronto thanks NSERC Canada for funding.

References

First citationBallantine, M., Menard, M. L. & Tam, W. (2009). J. Org. Chem. 74, 7570–7573.  Web of Science CrossRef PubMed CAS Google Scholar
First citationBernstein, 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
First citationBruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLough, A. J., Jack, K. & Tam, W. (2012a). Acta Cryst. E68, o2961.  CSD CrossRef IUCr Journals Google Scholar
First citationLough, A. J., Jack, K. & Tam, W. (2012b). Acta Cryst. E68, o2963.  CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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