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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1739.
Published online 2010 June 23. doi:  10.1107/S1600536810023391
PMCID: PMC3006834

Di-tert-butyl 2,2′-[(biphenyl-4,4′-diyl)­dioxy]diacetate

Abstract

The complete molecule of the title compound, C24H30O6, is generated by a crystallographic inversion centre. In the unique part of the mol­ecule, the four-atom –O–CH2–C(= O)–O– chain between the benzene ring and the tert-butyl group assumes a zigzag conformation [O—C—C—O torsion angle = −162.3 (1)°].

Related literature

For a related structure, see: Shah et al. (2010 [triangle]).

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Object name is e-66-o1739-scheme1.jpg

Experimental

Crystal data

  • C24H30O6
  • M r = 414.48
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1739-efi1.jpg
  • a = 9.9390 (7) Å
  • b = 12.6247 (8) Å
  • c = 9.8458 (7) Å
  • β = 114.645 (1)°
  • V = 1122.88 (13) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.4 × 0.3 × 0.2 mm

Data collection

  • Bruker SMART APEX diffractometer
  • 7450 measured reflections
  • 2572 independent reflections
  • 2029 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.120
  • S = 1.02
  • 2572 reflections
  • 136 parameters
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [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, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023391/lh5072sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023391/lh5072Isup2.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

Comment

We are interested in the solid-state structures of V-shaped molecules; recently we reported the crystal structure of 9,9-bis[4-(tert-butoxycarbonylmethyloxy)phenyl]fluorene (Shah et al., 2010). For such a shape, the number of carbon atoms making up the kink must be an odd number. In the present compound, the two aromatic rings are directly connected; the molecule lies on a center of symmetry (Fig. 1). The four-atom –O–CH2–C(═ O)–O– chain between the aromatic ring and the tert-butyl group assumes a zigzag conformation [O–C–C–O torsion angle 162.3 (1) °].

Experimental

4,4'-Dihydroxybiphenyl (1 g, 2.4 mmol) was dissolved in acetone (25 ml). To the solution was added potassium carbonate (0.67 g, 4.8 mmol) and t-butyl bromoacetate (0.75 ml, 4.8 mmol). The mixture was stirred at room temperature for 3 h. The solvent was evaporated under reduced pressure and the residue was dissolved in a mixture of water (50 ml) and dichloromethane (50 ml). The aqueous layer was extracted three times with dichloromethane. The combined organic phases were evaporated under reduced pressure and the solid material was recrystallized from n-hexane.

Refinement

H-atoms were placed in calculated positions [C–H 0.93–0.97 Å, U(H) 1.2–1.5U(C)] and were included in the refinement in the riding model approximation.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C24H30O6 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. Symmetry code: (i) = 1 - x, 1 - y, 1 - z.

Crystal data

C24H30O6F(000) = 444
Mr = 414.48Dx = 1.226 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2683 reflections
a = 9.9390 (7) Åθ = 2.8–28.4°
b = 12.6247 (8) ŵ = 0.09 mm1
c = 9.8458 (7) ÅT = 293 K
β = 114.645 (1)°Block, colorless
V = 1122.88 (13) Å30.4 × 0.3 × 0.2 mm
Z = 2

Data collection

Bruker SMART APEX diffractometer2029 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
graphiteθmax = 27.5°, θmin = 2.3°
ω scansh = −9→12
7450 measured reflectionsk = −15→16
2572 independent reflectionsl = −12→12

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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0597P)2 + 0.1713P] where P = (Fo2 + 2Fc2)/3
2572 reflections(Δ/σ)max = 0.001
136 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = −0.14 e Å3

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

xyzUiso*/Ueq
O10.16964 (10)1.03985 (7)0.42919 (10)0.0453 (2)
O20.24672 (13)0.91302 (9)0.31464 (12)0.0643 (3)
O30.49943 (10)0.88751 (7)0.57432 (12)0.0538 (3)
C10.03883 (16)1.07454 (11)0.29402 (15)0.0507 (4)
C20.0877 (2)1.11440 (17)0.1761 (2)0.0784 (5)
H2A0.12561.05630.13970.118*
H2B0.16361.16690.21930.118*
H2C0.00471.14520.09490.118*
C3−0.0216 (2)1.16473 (14)0.3541 (2)0.0726 (5)
H3A−0.05481.13760.42600.109*
H3B−0.10321.19730.27330.109*
H3C0.05481.21630.40100.109*
C4−0.07095 (18)0.98421 (15)0.2398 (2)0.0708 (5)
H4A−0.09850.96290.31840.106*
H4B−0.02660.92550.21190.106*
H4C−0.15741.00700.15490.106*
C50.25888 (15)0.96225 (10)0.42366 (15)0.0434 (3)
C60.37853 (15)0.94408 (10)0.57882 (16)0.0474 (3)
H6A0.41291.01180.62740.057*
H6B0.33770.90460.63740.057*
C70.48857 (14)0.77893 (10)0.55146 (14)0.0430 (3)
C80.40501 (16)0.71184 (11)0.59620 (17)0.0501 (3)
H80.34540.73910.63980.060*
C90.41070 (15)0.60337 (10)0.57559 (15)0.0465 (3)
H90.35430.55890.60660.056*
C100.49740 (13)0.55858 (9)0.51049 (13)0.0372 (3)
C110.58025 (16)0.62869 (11)0.46692 (16)0.0485 (3)
H110.63990.60200.42300.058*
C120.57629 (16)0.73697 (11)0.48722 (17)0.0513 (4)
H120.63320.78170.45730.062*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0429 (5)0.0464 (5)0.0447 (5)0.0080 (4)0.0165 (4)−0.0013 (4)
O20.0713 (7)0.0657 (7)0.0547 (6)0.0123 (5)0.0250 (5)−0.0130 (5)
O30.0412 (5)0.0355 (5)0.0814 (7)0.0021 (4)0.0224 (5)−0.0019 (4)
C10.0454 (7)0.0560 (8)0.0483 (7)0.0088 (6)0.0171 (6)0.0094 (6)
C20.0807 (12)0.0946 (14)0.0670 (11)0.0121 (10)0.0378 (10)0.0271 (9)
C30.0677 (11)0.0677 (11)0.0821 (11)0.0265 (9)0.0309 (9)0.0127 (9)
C40.0509 (9)0.0787 (11)0.0664 (10)−0.0030 (8)0.0082 (8)0.0053 (8)
C50.0447 (7)0.0381 (6)0.0503 (7)−0.0006 (5)0.0227 (6)−0.0037 (5)
C60.0470 (7)0.0381 (6)0.0538 (8)0.0051 (5)0.0177 (6)−0.0026 (5)
C70.0361 (6)0.0364 (6)0.0503 (7)0.0024 (5)0.0117 (5)0.0010 (5)
C80.0493 (8)0.0448 (7)0.0637 (8)−0.0005 (6)0.0312 (7)−0.0061 (6)
C90.0489 (7)0.0417 (7)0.0549 (8)−0.0054 (6)0.0277 (6)−0.0014 (5)
C100.0341 (6)0.0379 (6)0.0359 (6)0.0010 (5)0.0109 (5)0.0033 (5)
C110.0487 (7)0.0415 (7)0.0645 (8)0.0046 (6)0.0327 (7)0.0058 (6)
C120.0485 (8)0.0399 (7)0.0715 (9)0.0004 (6)0.0310 (7)0.0085 (6)

Geometric parameters (Å, °)

O1—C51.3379 (15)C4—H4C0.9600
O1—C11.4867 (16)C5—C61.5118 (19)
O2—C51.2020 (16)C6—H6A0.9700
O3—C71.3861 (15)C6—H6B0.9700
O3—C61.4143 (16)C7—C121.3787 (19)
C1—C41.513 (2)C7—C81.3807 (19)
C1—C21.519 (2)C8—C91.3890 (19)
C1—C31.518 (2)C8—H80.9300
C2—H2A0.9600C9—C101.3905 (18)
C2—H2B0.9600C9—H90.9300
C2—H2C0.9600C10—C111.3929 (18)
C3—H3A0.9600C10—C10i1.497 (2)
C3—H3B0.9600C11—C121.3845 (19)
C3—H3C0.9600C11—H110.9300
C4—H4A0.9600C12—H120.9300
C4—H4B0.9600
C5—O1—C1121.76 (10)O2—C5—C6124.59 (12)
C7—O3—C6119.66 (10)O1—C5—C6108.99 (10)
O1—C1—C4109.05 (11)O3—C6—C5111.44 (11)
O1—C1—C2110.05 (12)O3—C6—H6A109.3
C4—C1—C2113.18 (14)C5—C6—H6A109.3
O1—C1—C3102.28 (12)O3—C6—H6B109.3
C4—C1—C3110.99 (14)C5—C6—H6B109.3
C2—C1—C3110.73 (14)H6A—C6—H6B108.0
C1—C2—H2A109.5C12—C7—C8119.36 (12)
C1—C2—H2B109.5C12—C7—O3115.67 (12)
H2A—C2—H2B109.5C8—C7—O3124.85 (12)
C1—C2—H2C109.5C7—C8—C9119.45 (13)
H2A—C2—H2C109.5C7—C8—H8120.3
H2B—C2—H2C109.5C9—C8—H8120.3
C1—C3—H3A109.5C8—C9—C10122.62 (12)
C1—C3—H3B109.5C8—C9—H9118.7
H3A—C3—H3B109.5C10—C9—H9118.7
C1—C3—H3C109.5C9—C10—C11116.31 (11)
H3A—C3—H3C109.5C9—C10—C10i121.94 (14)
H3B—C3—H3C109.5C11—C10—C10i121.75 (14)
C1—C4—H4A109.5C12—C11—C10121.79 (13)
C1—C4—H4B109.5C12—C11—H11119.1
H4A—C4—H4B109.5C10—C11—H11119.1
C1—C4—H4C109.5C7—C12—C11120.47 (13)
H4A—C4—H4C109.5C7—C12—H12119.8
H4B—C4—H4C109.5C11—C12—H12119.8
O2—C5—O1126.41 (13)
C5—O1—C1—C464.56 (16)C12—C7—C8—C9−0.1 (2)
C5—O1—C1—C2−60.14 (17)O3—C7—C8—C9−175.79 (13)
C5—O1—C1—C3−177.86 (12)C7—C8—C9—C10−0.3 (2)
C1—O1—C5—O20.4 (2)C8—C9—C10—C110.3 (2)
C1—O1—C5—C6−178.70 (11)C8—C9—C10—C10i179.82 (14)
C7—O3—C6—C5−77.86 (15)C9—C10—C11—C12−0.1 (2)
O2—C5—C6—O318.60 (19)C10i—C10—C11—C12−179.55 (14)
O1—C5—C6—O3−162.30 (10)C8—C7—C12—C110.3 (2)
C6—O3—C7—C12153.70 (12)O3—C7—C12—C11176.43 (12)
C6—O3—C7—C8−30.43 (19)C10—C11—C12—C7−0.3 (2)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5072).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2002). SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Shah, K., Yousuf, S., Raza Shah, M. & Ng, S. W. (2010). Acta Cryst. E66, o1705. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). publCIF In preparation.

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