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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o912.
Published online 2009 March 28. doi:  10.1107/S1600536809010836
PMCID: PMC2968877

Di-tert-butyl (1,1′-binaphthyl-2,2′-di­oxy)diacetate

Abstract

In the crystal structure of the title compound, C32H34O6, the mol­ecule is located on a twofold rotation axis. The two naphthyl fused-ring systems are aligned at 72.6 (1)°. Weak intermolecular C—H(...)O hydrogen bonding is present in the crystal structure.

Related literature

For the crystal structure of the parent carboxylic acid, see: Wu et al. (2007 [triangle]).

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Object name is e-65-0o912-scheme1.jpg

Experimental

Crystal data

  • C32H34O6
  • M r = 514.59
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o912-efi1.jpg
  • a = 18.7604 (3) Å
  • b = 14.3204 (3) Å
  • c = 10.9997 (2) Å
  • β = 110.144 (1)°
  • V = 2774.37 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 133 K
  • 0.30 × 0.15 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 12968 measured reflections
  • 3198 independent reflections
  • 2514 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.121
  • S = 1.01
  • 3198 reflections
  • 175 parameters
  • H-atom parameters constrained
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010836/xu2499sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010836/xu2499Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the Higher Education Commission of Pakistan and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

Potassium carbonate (0.97 g, 7 mmol) and 1,1'-binaphthyl-2,2'-diol (0.57 mg, 2 mmol) in acetone (20 ml) were stirred for 15 minutes. tert-Butyl 2-bromoacetate (1.95 g, 10 mmol) was added and the mixture was stirred at 323 K for 2 h. The solvent was removed and the residue was dissolved in a mixture of water (50 ml) and dichloromethane (50 ml). The two phases were separated and the aqueous layer was extracted with dichloromethane. The combined organic phases were dried and the solvent evaporated. The residue was dissolved recrysstallized from dichloromethane (0.82 mg, 80% yield).

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) plot of C32H34O6 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C32H34O6F(000) = 1096
Mr = 514.59Dx = 1.232 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3672 reflections
a = 18.7604 (3) Åθ = 2.3–28.2°
b = 14.3204 (3) ŵ = 0.08 mm1
c = 10.9997 (2) ÅT = 133 K
β = 110.144 (1)°Block, colorless
V = 2774.37 (9) Å30.30 × 0.15 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer2514 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
graphiteθmax = 27.5°, θmin = 1.8°
ω scansh = −24→24
12968 measured reflectionsk = −18→18
3198 independent reflectionsl = −14→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0548P)2 + 1.9389P] where P = (Fo2 + 2Fc2)/3
3198 reflections(Δ/σ)max = 0.001
175 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = −0.20 e Å3

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

xyzUiso*/Ueq
O10.38962 (5)0.53557 (7)0.23963 (9)0.0278 (2)
O20.28361 (6)0.45195 (10)0.03634 (11)0.0531 (4)
O30.19998 (5)0.45848 (7)0.14254 (9)0.0292 (2)
C10.49788 (7)0.63074 (9)0.31656 (11)0.0219 (3)
C20.55167 (7)0.68166 (9)0.41843 (12)0.0255 (3)
C30.61052 (8)0.73495 (10)0.39965 (14)0.0326 (3)
H30.61620.73520.31710.039*
C40.65937 (10)0.78615 (12)0.49836 (16)0.0441 (4)
H40.69800.82230.48330.053*
C50.65281 (11)0.78558 (13)0.62268 (16)0.0503 (5)
H50.68690.82130.69080.060*
C60.59820 (10)0.73436 (12)0.64444 (15)0.0437 (4)
H60.59480.73360.72860.052*
C70.54571 (8)0.68154 (10)0.54431 (13)0.0314 (3)
C80.48693 (8)0.62974 (12)0.56391 (13)0.0350 (3)
H80.48330.62830.64790.042*
C90.43514 (8)0.58162 (11)0.46649 (13)0.0310 (3)
H90.39580.54740.48240.037*
C100.44042 (7)0.58301 (9)0.34153 (12)0.0242 (3)
C110.32140 (7)0.50678 (11)0.25672 (13)0.0291 (3)
H11A0.29790.56030.28570.035*
H11B0.33240.45750.32380.035*
C120.26778 (8)0.46984 (10)0.13024 (14)0.0304 (3)
C130.13800 (8)0.40721 (10)0.04369 (14)0.0315 (3)
C140.16385 (11)0.30839 (13)0.0342 (2)0.0556 (5)
H14A0.18560.28170.12130.083*
H14B0.20230.3087−0.00750.083*
H14C0.12040.2706−0.01730.083*
C150.11375 (9)0.45879 (14)−0.08469 (15)0.0439 (4)
H15A0.10280.5241−0.07100.066*
H15B0.06810.4294−0.14510.066*
H15C0.15470.4562−0.12080.066*
C160.07523 (8)0.40965 (12)0.10104 (15)0.0394 (4)
H16A0.09300.37990.18650.059*
H16B0.03080.37600.04400.059*
H16C0.06130.47460.10970.059*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0218 (5)0.0396 (6)0.0254 (5)−0.0038 (4)0.0123 (4)−0.0006 (4)
O20.0342 (6)0.0883 (10)0.0461 (7)−0.0154 (6)0.0255 (5)−0.0245 (6)
O30.0220 (5)0.0364 (5)0.0321 (5)−0.0025 (4)0.0131 (4)−0.0021 (4)
C10.0220 (6)0.0255 (6)0.0194 (6)0.0059 (5)0.0088 (5)0.0020 (5)
C20.0265 (7)0.0256 (6)0.0225 (6)0.0064 (5)0.0062 (5)−0.0007 (5)
C30.0345 (7)0.0302 (7)0.0292 (7)−0.0021 (6)0.0061 (6)−0.0016 (6)
C40.0416 (9)0.0373 (8)0.0456 (9)−0.0091 (7)0.0050 (7)−0.0067 (7)
C50.0545 (10)0.0477 (10)0.0339 (8)−0.0049 (8)−0.0037 (8)−0.0146 (7)
C60.0508 (10)0.0487 (9)0.0261 (7)0.0031 (8)0.0060 (7)−0.0089 (7)
C70.0340 (7)0.0357 (7)0.0214 (6)0.0105 (6)0.0054 (6)−0.0029 (5)
C80.0367 (8)0.0513 (9)0.0199 (6)0.0129 (7)0.0134 (6)0.0035 (6)
C90.0282 (7)0.0447 (8)0.0241 (7)0.0072 (6)0.0142 (6)0.0064 (6)
C100.0218 (6)0.0310 (7)0.0213 (6)0.0062 (5)0.0094 (5)0.0035 (5)
C110.0223 (6)0.0385 (8)0.0310 (7)0.0016 (5)0.0150 (6)0.0050 (6)
C120.0249 (7)0.0345 (7)0.0359 (7)−0.0004 (6)0.0157 (6)−0.0007 (6)
C130.0240 (6)0.0332 (7)0.0377 (8)−0.0051 (6)0.0110 (6)−0.0043 (6)
C140.0443 (10)0.0366 (9)0.0848 (14)−0.0032 (8)0.0207 (10)−0.0131 (9)
C150.0359 (8)0.0621 (11)0.0335 (8)−0.0065 (8)0.0118 (7)0.0006 (7)
C160.0262 (7)0.0516 (10)0.0419 (9)−0.0063 (7)0.0138 (6)0.0024 (7)

Geometric parameters (Å, °)

O1—C101.3749 (16)C8—C91.360 (2)
O1—C111.4174 (15)C8—H80.9500
O2—C121.1966 (17)C9—C101.4118 (17)
O3—C121.3347 (15)C9—H90.9500
O3—C131.4842 (16)C11—C121.504 (2)
C1—C101.3815 (17)C11—H11A0.9900
C1—C21.4237 (18)C11—H11B0.9900
C1—C1i1.494 (2)C13—C141.511 (2)
C2—C31.415 (2)C13—C161.5158 (19)
C2—C71.4270 (18)C13—C151.518 (2)
C3—C41.368 (2)C14—H14A0.9800
C3—H30.9500C14—H14B0.9800
C4—C51.415 (2)C14—H14C0.9800
C4—H40.9500C15—H15A0.9800
C5—C61.347 (3)C15—H15B0.9800
C5—H50.9500C15—H15C0.9800
C6—C71.417 (2)C16—H16A0.9800
C6—H60.9500C16—H16B0.9800
C7—C81.406 (2)C16—H16C0.9800
C10—O1—C11116.08 (10)O1—C11—H11A109.9
C12—O3—C13121.30 (11)C12—C11—H11A109.9
C10—C1—C2119.15 (11)O1—C11—H11B109.9
C10—C1—C1i120.24 (12)C12—C11—H11B109.9
C2—C1—C1i120.60 (12)H11A—C11—H11B108.3
C3—C2—C1122.59 (12)O2—C12—O3126.15 (14)
C3—C2—C7117.92 (13)O2—C12—C11126.00 (13)
C1—C2—C7119.47 (12)O3—C12—C11107.83 (11)
C4—C3—C2121.09 (14)O3—C13—C14108.95 (12)
C4—C3—H3119.5O3—C13—C16102.04 (11)
C2—C3—H3119.5C14—C13—C16111.35 (14)
C3—C4—C5120.45 (16)O3—C13—C15110.43 (12)
C3—C4—H4119.8C14—C13—C15113.09 (15)
C5—C4—H4119.8C16—C13—C15110.43 (13)
C6—C5—C4119.97 (15)C13—C14—H14A109.5
C6—C5—H5120.0C13—C14—H14B109.5
C4—C5—H5120.0H14A—C14—H14B109.5
C5—C6—C7121.34 (15)C13—C14—H14C109.5
C5—C6—H6119.3H14A—C14—H14C109.5
C7—C6—H6119.3H14B—C14—H14C109.5
C8—C7—C6122.29 (13)C13—C15—H15A109.5
C8—C7—C2118.50 (13)C13—C15—H15B109.5
C6—C7—C2119.20 (14)H15A—C15—H15B109.5
C9—C8—C7122.11 (12)C13—C15—H15C109.5
C9—C8—H8118.9H15A—C15—H15C109.5
C7—C8—H8118.9H15B—C15—H15C109.5
C8—C9—C10119.30 (13)C13—C16—H16A109.5
C8—C9—H9120.3C13—C16—H16B109.5
C10—C9—H9120.3H16A—C16—H16B109.5
O1—C10—C1116.85 (10)C13—C16—H16C109.5
O1—C10—C9121.70 (12)H16A—C16—H16C109.5
C1—C10—C9121.44 (12)H16B—C16—H16C109.5
O1—C11—C12109.05 (10)
C10—C1—C2—C3−177.72 (12)C7—C8—C9—C100.3 (2)
C1i—C1—C2—C30.71 (18)C11—O1—C10—C1−164.92 (11)
C10—C1—C2—C70.70 (18)C11—O1—C10—C916.29 (18)
C1i—C1—C2—C7179.14 (11)C2—C1—C10—O1179.49 (11)
C1—C2—C3—C4177.29 (13)C1i—C1—C10—O11.05 (16)
C7—C2—C3—C4−1.2 (2)C2—C1—C10—C9−1.72 (19)
C2—C3—C4—C51.1 (2)C1i—C1—C10—C9179.83 (11)
C3—C4—C5—C60.0 (3)C8—C9—C10—O1179.96 (12)
C4—C5—C6—C7−1.0 (3)C8—C9—C10—C11.2 (2)
C5—C6—C7—C8−178.13 (16)C10—O1—C11—C12171.26 (11)
C5—C6—C7—C20.9 (2)C13—O3—C12—O29.7 (2)
C3—C2—C7—C8179.26 (13)C13—O3—C12—C11−168.85 (11)
C1—C2—C7—C80.76 (19)O1—C11—C12—O212.1 (2)
C3—C2—C7—C60.2 (2)O1—C11—C12—O3−169.43 (11)
C1—C2—C7—C6−178.34 (13)C12—O3—C13—C1460.23 (17)
C6—C7—C8—C9177.77 (14)C12—O3—C13—C16178.05 (13)
C2—C7—C8—C9−1.3 (2)C12—O3—C13—C15−64.54 (16)

Symmetry codes: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C9—H9···O2ii0.952.383.226 (2)149

Symmetry codes: (ii) x, −y+1, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2499).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.
  • Wu, Y.-M., Cao, G.-Q., Qian, M.-Y. & Zhu, H.-J. (2007). Acta Cryst. E63, o3446.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography