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

Ali, Q.; Yousuf, S.; Raza Shah, M.; Ng, S.W.

doi:10.1107/S1600536810023391

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1739

doi:10.1107/S1600536810023391

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

Qamar Ali,^a Sammer Yousuf,^a Muhammad Raza Shah ^a and Seik Weng Ng ^b ^*

^aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 15 June 2010; accepted 16 June 2010; online 23 June 2010)

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 ).

Experimental

Crystal data

C₂₄H₃₀O₆
M_r = 414.48
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.120
S = 1.02
2572 reflections
136 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

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

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023391/lh5072Isup2.hkl

checkCIF report

Comment top

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) °].

Related literature top

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

Experimental top

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.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

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.

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

Crystal data top

C₂₄H₃₀O₆	F(000) = 444
M_r = 414.48	D_x = 1.226 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2683 reflections
a = 9.9390 (7) Å	θ = 2.8–28.4°
b = 12.6247 (8) Å	µ = 0.09 mm⁻¹
c = 9.8458 (7) Å	T = 293 K
β = 114.645 (1)°	Block, colorless
V = 1122.88 (13) Å³	0.4 × 0.3 × 0.2 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	2029 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.024
Graphite monochromator	θ_max = 27.5°, θ_min = 2.3°
ω scans	h = −9→12
7450 measured reflections	k = −15→16
2572 independent reflections	l = −12→12

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0597P)² + 0.1713P] where P = (F_o² + 2F_c²)/3
2572 reflections	(Δ/σ)_max = 0.001
136 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₄H₃₀O₆	V = 1122.88 (13) Å³
M_r = 414.48	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.9390 (7) Å	µ = 0.09 mm⁻¹
b = 12.6247 (8) Å	T = 293 K
c = 9.8458 (7) Å	0.4 × 0.3 × 0.2 mm
β = 114.645 (1)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.02	Δρ_max = 0.16 e Å⁻³
2572 reflections	Δρ_min = −0.14 e Å⁻³
136 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.16964 (10)	1.03985 (7)	0.42919 (10)	0.0453 (2)
O2	0.24672 (13)	0.91302 (9)	0.31464 (12)	0.0643 (3)
O3	0.49943 (10)	0.88751 (7)	0.57432 (12)	0.0538 (3)
C1	0.03883 (16)	1.07454 (11)	0.29402 (15)	0.0507 (4)
C2	0.0877 (2)	1.11440 (17)	0.1761 (2)	0.0784 (5)
H2A	0.1256	1.0563	0.1397	0.118*
H2B	0.1636	1.1669	0.2193	0.118*
H2C	0.0047	1.1452	0.0949	0.118*
C3	−0.0216 (2)	1.16473 (14)	0.3541 (2)	0.0726 (5)
H3A	−0.0548	1.1376	0.4260	0.109*
H3B	−0.1032	1.1973	0.2733	0.109*
H3C	0.0548	1.2163	0.4010	0.109*
C4	−0.07095 (18)	0.98421 (15)	0.2398 (2)	0.0708 (5)
H4A	−0.0985	0.9629	0.3184	0.106*
H4B	−0.0266	0.9255	0.2119	0.106*
H4C	−0.1574	1.0070	0.1549	0.106*
C5	0.25888 (15)	0.96225 (10)	0.42366 (15)	0.0434 (3)
C6	0.37853 (15)	0.94408 (10)	0.57882 (16)	0.0474 (3)
H6A	0.4129	1.0118	0.6274	0.057*
H6B	0.3377	0.9046	0.6374	0.057*
C7	0.48857 (14)	0.77893 (10)	0.55146 (14)	0.0430 (3)
C8	0.40501 (16)	0.71184 (11)	0.59620 (17)	0.0501 (3)
H8	0.3454	0.7391	0.6398	0.060*
C9	0.41070 (15)	0.60337 (10)	0.57559 (15)	0.0465 (3)
H9	0.3543	0.5589	0.6066	0.056*
C10	0.49740 (13)	0.55858 (9)	0.51049 (13)	0.0372 (3)
C11	0.58025 (16)	0.62869 (11)	0.46692 (16)	0.0485 (3)
H11	0.6399	0.6020	0.4230	0.058*
C12	0.57629 (16)	0.73697 (11)	0.48722 (17)	0.0513 (4)
H12	0.6332	0.7817	0.4573	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0429 (5)	0.0464 (5)	0.0447 (5)	0.0080 (4)	0.0165 (4)	−0.0013 (4)
O2	0.0713 (7)	0.0657 (7)	0.0547 (6)	0.0123 (5)	0.0250 (5)	−0.0130 (5)
O3	0.0412 (5)	0.0355 (5)	0.0814 (7)	0.0021 (4)	0.0224 (5)	−0.0019 (4)
C1	0.0454 (7)	0.0560 (8)	0.0483 (7)	0.0088 (6)	0.0171 (6)	0.0094 (6)
C2	0.0807 (12)	0.0946 (14)	0.0670 (11)	0.0121 (10)	0.0378 (10)	0.0271 (9)
C3	0.0677 (11)	0.0677 (11)	0.0821 (11)	0.0265 (9)	0.0309 (9)	0.0127 (9)
C4	0.0509 (9)	0.0787 (11)	0.0664 (10)	−0.0030 (8)	0.0082 (8)	0.0053 (8)
C5	0.0447 (7)	0.0381 (6)	0.0503 (7)	−0.0006 (5)	0.0227 (6)	−0.0037 (5)
C6	0.0470 (7)	0.0381 (6)	0.0538 (8)	0.0051 (5)	0.0177 (6)	−0.0026 (5)
C7	0.0361 (6)	0.0364 (6)	0.0503 (7)	0.0024 (5)	0.0117 (5)	0.0010 (5)
C8	0.0493 (8)	0.0448 (7)	0.0637 (8)	−0.0005 (6)	0.0312 (7)	−0.0061 (6)
C9	0.0489 (7)	0.0417 (7)	0.0549 (8)	−0.0054 (6)	0.0277 (6)	−0.0014 (5)
C10	0.0341 (6)	0.0379 (6)	0.0359 (6)	0.0010 (5)	0.0109 (5)	0.0033 (5)
C11	0.0487 (7)	0.0415 (7)	0.0645 (8)	0.0046 (6)	0.0327 (7)	0.0058 (6)
C12	0.0485 (8)	0.0399 (7)	0.0715 (9)	0.0004 (6)	0.0310 (7)	0.0085 (6)

Geometric parameters (Å, º) top

O1—C5	1.3379 (15)	C4—H4C	0.9600
O1—C1	1.4867 (16)	C5—C6	1.5118 (19)
O2—C5	1.2020 (16)	C6—H6A	0.9700
O3—C7	1.3861 (15)	C6—H6B	0.9700
O3—C6	1.4143 (16)	C7—C12	1.3787 (19)
C1—C4	1.513 (2)	C7—C8	1.3807 (19)
C1—C2	1.519 (2)	C8—C9	1.3890 (19)
C1—C3	1.518 (2)	C8—H8	0.9300
C2—H2A	0.9600	C9—C10	1.3905 (18)
C2—H2B	0.9600	C9—H9	0.9300
C2—H2C	0.9600	C10—C11	1.3929 (18)
C3—H3A	0.9600	C10—C10ⁱ	1.497 (2)
C3—H3B	0.9600	C11—C12	1.3845 (19)
C3—H3C	0.9600	C11—H11	0.9300
C4—H4A	0.9600	C12—H12	0.9300
C4—H4B	0.9600

C5—O1—C1	121.76 (10)	O2—C5—C6	124.59 (12)
C7—O3—C6	119.66 (10)	O1—C5—C6	108.99 (10)
O1—C1—C4	109.05 (11)	O3—C6—C5	111.44 (11)
O1—C1—C2	110.05 (12)	O3—C6—H6A	109.3
C4—C1—C2	113.18 (14)	C5—C6—H6A	109.3
O1—C1—C3	102.28 (12)	O3—C6—H6B	109.3
C4—C1—C3	110.99 (14)	C5—C6—H6B	109.3
C2—C1—C3	110.73 (14)	H6A—C6—H6B	108.0
C1—C2—H2A	109.5	C12—C7—C8	119.36 (12)
C1—C2—H2B	109.5	C12—C7—O3	115.67 (12)
H2A—C2—H2B	109.5	C8—C7—O3	124.85 (12)
C1—C2—H2C	109.5	C7—C8—C9	119.45 (13)
H2A—C2—H2C	109.5	C7—C8—H8	120.3
H2B—C2—H2C	109.5	C9—C8—H8	120.3
C1—C3—H3A	109.5	C8—C9—C10	122.62 (12)
C1—C3—H3B	109.5	C8—C9—H9	118.7
H3A—C3—H3B	109.5	C10—C9—H9	118.7
C1—C3—H3C	109.5	C9—C10—C11	116.31 (11)
H3A—C3—H3C	109.5	C9—C10—C10ⁱ	121.94 (14)
H3B—C3—H3C	109.5	C11—C10—C10ⁱ	121.75 (14)
C1—C4—H4A	109.5	C12—C11—C10	121.79 (13)
C1—C4—H4B	109.5	C12—C11—H11	119.1
H4A—C4—H4B	109.5	C10—C11—H11	119.1
C1—C4—H4C	109.5	C7—C12—C11	120.47 (13)
H4A—C4—H4C	109.5	C7—C12—H12	119.8
H4B—C4—H4C	109.5	C11—C12—H12	119.8
O2—C5—O1	126.41 (13)

C5—O1—C1—C4	64.56 (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—O2	0.4 (2)	C8—C9—C10—C11	0.3 (2)
C1—O1—C5—C6	−178.70 (11)	C8—C9—C10—C10ⁱ	179.82 (14)
C7—O3—C6—C5	−77.86 (15)	C9—C10—C11—C12	−0.1 (2)
O2—C5—C6—O3	18.60 (19)	C10ⁱ—C10—C11—C12	−179.55 (14)
O1—C5—C6—O3	−162.30 (10)	C8—C7—C12—C11	0.3 (2)
C6—O3—C7—C12	153.70 (12)	O3—C7—C12—C11	176.43 (12)
C6—O3—C7—C8	−30.43 (19)	C10—C11—C12—C7	−0.3 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₃₀O₆
M_r	414.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.9390 (7), 12.6247 (8), 9.8458 (7)
β (°)	114.645 (1)
V (Å³)	1122.88 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.4 × 0.3 × 0.2

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7450, 2572, 2029
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.120, 1.02
No. of reflections	2572
No. of parameters	136
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.14

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

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

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Shah, K., Yousuf, S., Raza Shah, M. & Ng, S. W. (2010). Acta Cryst. E66, o1705. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Westrip, S. P. (2010). publCIF. In preparation. Google Scholar