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

The complete molecule of the title compound, C(24)H(30)O(6), is generated by a crystallographic inversion centre. In the unique part of the mol-ecule, the four-atom -O-CH(2)-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 = 414.48

Monoclinic,

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 ▶); 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 ▶).

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

C24H30O6	F(000) = 444
Mr = 414.48	Dx = 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

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

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(Fo2) + (0.0597P)2 + 0.1713P] where P = (Fo2 + 2Fc2)/3
2572 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)