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

The title compound, C(24)H(30)O(6), does not exhibit π-π inter-actions due to the steric effect of the bulky tert-butyl groups present in the mol-ecule. The presence of these groups at the 2 and 2' positions hinders the free motion of the benzene rings relative to each other, causing them to adopt an anti-periplanar arrangement. The benzene rings are twisted by just under 50.96 (17)° with respect to each other. The carbonyl groups within the mol-ecule are directed in different directions, one towards the biphenyl group and the other away from it. The mol-ecules are linked together by C=O⋯H-C hydrogen bonds.

Related literature

For general background on chemical and biological studies of biphenyl compounds, see: Toshiaki et al. (2007 ▶); Kamoda et al. (2006 ▶); Makarov et al. (2005 ▶); Weisburger et al. (1967 ▶); Spivey et al. (1999 ▶); Sisson et al. (2006 ▶); Litvinchuk et al. (2004 ▶); Baudry et al. (2006 ▶). For the crystal structures of related compounds, see: Ali et al. (2008 ▶); Ibad et al. (2008 ▶).

Experimental

Crystal data

C24H30O6

M = 414.48

Triclinic,

a = 7.7458 (15) Å

b = 12.112 (2) Å

c = 13.480 (3) Å

α = 67.36 (3)°

β = 82.11 (3)°

γ = 82.68 (3)°

V = 1152.3 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 153 (2) K

0.48 × 0.38 × 0.19 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.960, T max = 0.984

8742 measured reflections

4191 independent reflections

3687 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.113

S = 1.06

4191 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019764/ez2127sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019764/ez2127Isup2.hkl

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

C24H30O6	Z = 2
Mr = 414.48	F000 = 444
Triclinic, P1	Dx = 1.195 Mg m−3
a = 7.7458 (15) Å	Mo Kα radiation λ = 0.71073 Å
b = 12.112 (2) Å	Cell parameters from 3800 reflections
c = 13.480 (3) Å	θ = 3.0–26.4º
α = 67.36 (3)º	µ = 0.09 mm−1
β = 82.11 (3)º	T = 153 (2) K
γ = 82.68 (3)º	Chip, colorless
V = 1152.3 (4) Å3	0.48 × 0.38 × 0.19 mm

Rigaku Mercury CCD (2x2 bin mode) diffractometer	4191 independent reflections
Radiation source: Sealed Tube	3687 reflections with I > 2σ(I)
Monochromator: Graphite Monochromator	Rint = 0.012
Detector resolution: 14.6306 pixels mm-1	θmax = 25.4º
T = 153(2) K	θmin = 2.9º
ω scans	h = −9→9
Absorption correction: multi-scan(REQAB; Jacobson, 1998)	k = −14→14
Tmin = 0.960, Tmax = 0.984	l = −13→16
8742 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0624P)2 + 0.3008P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
4191 reflections	Δρmax = 0.20 e Å−3
271 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
O1	0.63964 (12)	0.48792 (8)	0.74773 (7)	0.0256 (2)
O2	0.67544 (15)	0.42265 (9)	0.92572 (8)	0.0407 (3)
O3	0.51537 (11)	0.70530 (8)	0.73639 (7)	0.0242 (2)
O4	0.22493 (12)	0.95936 (8)	0.46008 (7)	0.0279 (2)
O5	0.13650 (14)	0.94540 (8)	0.27408 (8)	0.0351 (2)
O6	0.14967 (12)	1.14648 (8)	0.18911 (7)	0.0285 (2)
C1	0.63803 (16)	0.49982 (12)	0.84152 (10)	0.0240 (3)
C2	0.58898 (17)	0.62861 (11)	0.83262 (10)	0.0249 (3)
H2A	0.5043	0.6279	0.8949	0.030*
H2B	0.6951	0.6628	0.8381	0.030*
C3	0.35750 (16)	0.67899 (11)	0.71761 (10)	0.0217 (3)
C4	0.24448 (17)	0.60667 (11)	0.79977 (11)	0.0264 (3)
H4A	0.2749	0.5724	0.8720	0.032*
C5	0.08664 (17)	0.58520 (12)	0.77493 (12)	0.0307 (3)
H5A	0.0099	0.5348	0.8302	0.037*
C6	0.04097 (17)	0.63678 (12)	0.67037 (12)	0.0306 (3)
H6A	−0.0676	0.6228	0.6539	0.037*
C7	0.15448 (16)	0.70935 (11)	0.58920 (11)	0.0258 (3)
H7A	0.1216	0.7451	0.5175	0.031*
C8	0.31533 (15)	0.73087 (10)	0.61059 (10)	0.0211 (3)
C9	0.44218 (16)	0.80053 (11)	0.52109 (10)	0.0219 (3)
C10	0.61274 (17)	0.75052 (13)	0.50921 (11)	0.0285 (3)
H10A	0.6473	0.6736	0.5598	0.034*
C11	0.73297 (18)	0.81058 (15)	0.42515 (12)	0.0372 (4)
H11A	0.8482	0.7749	0.4181	0.045*
C12	0.68340 (19)	0.92246 (16)	0.35221 (12)	0.0403 (4)
H12A	0.7657	0.9645	0.2952	0.048*
C13	0.51479 (18)	0.97446 (14)	0.36101 (11)	0.0335 (3)
H13A	0.4815	1.0514	0.3100	0.040*
C14	0.39452 (16)	0.91327 (12)	0.44496 (10)	0.0245 (3)
C15	0.16606 (19)	1.06562 (11)	0.37635 (11)	0.0284 (3)
H15A	0.2491	1.1275	0.3596	0.034*
H15B	0.0507	1.0966	0.4011	0.034*
C16	0.15050 (16)	1.04284 (11)	0.27501 (11)	0.0255 (3)
C17	0.67465 (19)	0.36897 (12)	0.73667 (12)	0.0309 (3)
C18	0.6458 (3)	0.40082 (18)	0.61993 (16)	0.0636 (6)
H18A	0.5237	0.4314	0.6089	0.095*
H18B	0.6720	0.3291	0.6017	0.095*
H18C	0.7230	0.4626	0.5734	0.095*
C19	0.5431 (3)	0.28453 (16)	0.81140 (19)	0.0589 (5)
H19A	0.5651	0.2644	0.8865	0.088*
H19B	0.5544	0.2110	0.7960	0.088*
H19C	0.4247	0.3235	0.8001	0.088*
C20	0.8607 (2)	0.32095 (15)	0.75818 (16)	0.0461 (4)
H20A	0.8746	0.3010	0.8345	0.069*
H20B	0.9400	0.3820	0.7131	0.069*
H20C	0.8886	0.2487	0.7410	0.069*
C21	0.12658 (19)	1.15005 (13)	0.08041 (11)	0.0313 (3)
C22	0.2762 (2)	1.07515 (15)	0.04516 (14)	0.0449 (4)
H22A	0.3876	1.1053	0.0455	0.067*
H22B	0.2633	1.0805	−0.0279	0.067*
H22C	0.2744	0.9913	0.0951	0.067*
C23	0.1343 (2)	1.28210 (13)	0.01004 (12)	0.0386 (4)
H23A	0.2499	1.3070	0.0098	0.058*
H23B	0.0444	1.3296	0.0387	0.058*
H23C	0.1136	1.2950	−0.0639	0.058*
C24	−0.0517 (2)	1.10931 (17)	0.08184 (13)	0.0458 (4)
H24A	−0.1431	1.1605	0.1051	0.069*
H24B	−0.0581	1.0258	0.1321	0.069*
H24C	−0.0689	1.1153	0.0092	0.069*

	U11	U22	U33	U12	U13	U23
O1	0.0307 (5)	0.0248 (5)	0.0223 (5)	−0.0003 (4)	−0.0047 (4)	−0.0096 (4)
O2	0.0582 (7)	0.0344 (6)	0.0223 (5)	0.0101 (5)	−0.0090 (5)	−0.0052 (5)
O3	0.0245 (4)	0.0238 (4)	0.0226 (5)	−0.0039 (3)	−0.0061 (4)	−0.0049 (4)
O4	0.0285 (5)	0.0244 (5)	0.0218 (5)	0.0031 (4)	−0.0014 (4)	−0.0005 (4)
O5	0.0451 (6)	0.0234 (5)	0.0360 (6)	−0.0064 (4)	−0.0066 (4)	−0.0080 (4)
O6	0.0397 (5)	0.0235 (5)	0.0207 (5)	−0.0042 (4)	−0.0067 (4)	−0.0047 (4)
C1	0.0232 (6)	0.0285 (7)	0.0181 (6)	−0.0020 (5)	−0.0023 (5)	−0.0064 (5)
C2	0.0276 (6)	0.0280 (7)	0.0189 (6)	−0.0018 (5)	−0.0060 (5)	−0.0075 (5)
C3	0.0206 (6)	0.0192 (6)	0.0246 (6)	0.0003 (5)	−0.0034 (5)	−0.0077 (5)
C4	0.0255 (6)	0.0241 (6)	0.0239 (7)	0.0006 (5)	−0.0018 (5)	−0.0036 (5)
C5	0.0238 (6)	0.0252 (7)	0.0341 (8)	−0.0028 (5)	0.0012 (5)	−0.0024 (6)
C6	0.0214 (6)	0.0272 (7)	0.0407 (8)	−0.0036 (5)	−0.0055 (6)	−0.0088 (6)
C7	0.0248 (6)	0.0235 (6)	0.0281 (7)	0.0001 (5)	−0.0068 (5)	−0.0078 (5)
C8	0.0212 (6)	0.0173 (6)	0.0236 (6)	0.0008 (4)	−0.0023 (5)	−0.0071 (5)
C9	0.0229 (6)	0.0245 (6)	0.0196 (6)	−0.0039 (5)	−0.0037 (5)	−0.0085 (5)
C10	0.0243 (6)	0.0354 (7)	0.0244 (7)	0.0010 (5)	−0.0050 (5)	−0.0097 (6)
C11	0.0215 (6)	0.0561 (9)	0.0304 (7)	−0.0012 (6)	−0.0013 (5)	−0.0131 (7)
C12	0.0288 (7)	0.0581 (10)	0.0264 (7)	−0.0125 (7)	0.0020 (6)	−0.0061 (7)
C13	0.0331 (7)	0.0362 (8)	0.0245 (7)	−0.0080 (6)	−0.0037 (6)	−0.0021 (6)
C14	0.0250 (6)	0.0270 (6)	0.0215 (6)	−0.0027 (5)	−0.0040 (5)	−0.0082 (5)
C15	0.0355 (7)	0.0203 (6)	0.0234 (7)	0.0032 (5)	−0.0056 (5)	−0.0024 (5)
C16	0.0244 (6)	0.0211 (6)	0.0268 (7)	−0.0015 (5)	−0.0040 (5)	−0.0040 (5)
C17	0.0370 (7)	0.0250 (7)	0.0348 (8)	−0.0033 (6)	−0.0037 (6)	−0.0155 (6)
C18	0.1049 (17)	0.0525 (11)	0.0492 (11)	0.0072 (11)	−0.0259 (11)	−0.0343 (10)
C19	0.0529 (10)	0.0426 (9)	0.0859 (15)	−0.0215 (8)	0.0172 (10)	−0.0317 (10)
C20	0.0403 (9)	0.0373 (8)	0.0676 (12)	0.0044 (7)	−0.0056 (8)	−0.0292 (8)
C21	0.0412 (8)	0.0321 (7)	0.0215 (7)	−0.0085 (6)	−0.0057 (6)	−0.0083 (6)
C22	0.0565 (10)	0.0422 (9)	0.0359 (9)	−0.0074 (7)	0.0058 (7)	−0.0166 (7)
C23	0.0557 (9)	0.0333 (8)	0.0239 (7)	−0.0079 (7)	−0.0098 (6)	−0.0041 (6)
C24	0.0480 (9)	0.0551 (10)	0.0339 (8)	−0.0188 (8)	−0.0107 (7)	−0.0095 (8)

O1—C1	1.3247 (16)	C12—H12A	0.9500
O1—C17	1.4921 (16)	C13—C14	1.3924 (19)
O2—C1	1.2044 (17)	C13—H13A	0.9500
O3—C3	1.3811 (15)	C15—C16	1.5168 (19)
O3—C2	1.4180 (16)	C15—H15A	0.9900
O4—C14	1.3805 (16)	C15—H15B	0.9900
O4—C15	1.4183 (16)	C17—C20	1.507 (2)
O5—C16	1.2038 (16)	C17—C18	1.511 (2)
O6—C16	1.3407 (17)	C17—C19	1.513 (2)
O6—C21	1.4839 (16)	C18—H18A	0.9800
C1—C2	1.5196 (18)	C18—H18B	0.9800
C2—H2A	0.9900	C18—H18C	0.9800
C2—H2B	0.9900	C19—H19A	0.9800
C3—C4	1.3939 (19)	C19—H19B	0.9800
C3—C8	1.4006 (18)	C19—H19C	0.9800
C4—C5	1.3910 (19)	C20—H20A	0.9800
C4—H4A	0.9500	C20—H20B	0.9800
C5—C6	1.380 (2)	C20—H20C	0.9800
C5—H5A	0.9500	C21—C23	1.517 (2)
C6—C7	1.391 (2)	C21—C22	1.518 (2)
C6—H6A	0.9500	C21—C24	1.520 (2)
C7—C8	1.3938 (17)	C22—H22A	0.9800
C7—H7A	0.9500	C22—H22B	0.9800
C8—C9	1.4950 (18)	C22—H22C	0.9800
C9—C10	1.3966 (19)	C23—H23A	0.9800
C9—C14	1.3967 (19)	C23—H23B	0.9800
C10—C11	1.389 (2)	C23—H23C	0.9800
C10—H10A	0.9500	C24—H24A	0.9800
C11—C12	1.377 (2)	C24—H24B	0.9800
C11—H11A	0.9500	C24—H24C	0.9800
C12—C13	1.386 (2)
C1—O1—C17	122.25 (11)	C16—C15—H15B	109.3
C3—O3—C2	117.83 (10)	H15A—C15—H15B	108.0
C14—O4—C15	116.99 (11)	O5—C16—O6	125.86 (13)
C16—O6—C21	121.03 (10)	O5—C16—C15	123.97 (12)
O2—C1—O1	126.99 (13)	O6—C16—C15	110.14 (11)
O2—C1—C2	120.93 (12)	O1—C17—C20	109.60 (11)
O1—C1—C2	112.04 (11)	O1—C17—C18	102.02 (12)
O3—C2—C1	115.22 (10)	C20—C17—C18	111.65 (15)
O3—C2—H2A	108.5	O1—C17—C19	109.59 (12)
C1—C2—H2A	108.5	C20—C17—C19	112.56 (14)
O3—C2—H2B	108.5	C18—C17—C19	110.90 (16)
C1—C2—H2B	108.5	C17—C18—H18A	109.5
H2A—C2—H2B	107.5	C17—C18—H18B	109.5
O3—C3—C4	122.53 (11)	H18A—C18—H18B	109.5
O3—C3—C8	116.03 (11)	C17—C18—H18C	109.5
C4—C3—C8	121.43 (11)	H18A—C18—H18C	109.5
C5—C4—C3	119.31 (12)	H18B—C18—H18C	109.5
C5—C4—H4A	120.3	C17—C19—H19A	109.5
C3—C4—H4A	120.3	C17—C19—H19B	109.5
C6—C5—C4	120.34 (12)	H19A—C19—H19B	109.5
C6—C5—H5A	119.8	C17—C19—H19C	109.5
C4—C5—H5A	119.8	H19A—C19—H19C	109.5
C5—C6—C7	119.79 (12)	H19B—C19—H19C	109.5
C5—C6—H6A	120.1	C17—C20—H20A	109.5
C7—C6—H6A	120.1	C17—C20—H20B	109.5
C6—C7—C8	121.50 (12)	H20A—C20—H20B	109.5
C6—C7—H7A	119.2	C17—C20—H20C	109.5
C8—C7—H7A	119.2	H20A—C20—H20C	109.5
C7—C8—C3	117.62 (12)	H20B—C20—H20C	109.5
C7—C8—C9	120.83 (11)	O6—C21—C23	102.98 (11)
C3—C8—C9	121.45 (11)	O6—C21—C22	109.69 (12)
C10—C9—C14	117.97 (12)	C23—C21—C22	110.79 (13)
C10—C9—C8	119.72 (11)	O6—C21—C24	109.62 (12)
C14—C9—C8	122.25 (11)	C23—C21—C24	110.38 (13)
C11—C10—C9	121.56 (13)	C22—C21—C24	112.92 (13)
C11—C10—H10A	119.2	C21—C22—H22A	109.5
C9—C10—H10A	119.2	C21—C22—H22B	109.5
C12—C11—C10	119.28 (14)	H22A—C22—H22B	109.5
C12—C11—H11A	120.4	C21—C22—H22C	109.5
C10—C11—H11A	120.4	H22A—C22—H22C	109.5
C11—C12—C13	120.73 (13)	H22B—C22—H22C	109.5
C11—C12—H12A	119.6	C21—C23—H23A	109.5
C13—C12—H12A	119.6	C21—C23—H23B	109.5
C12—C13—C14	119.66 (13)	H23A—C23—H23B	109.5
C12—C13—H13A	120.2	C21—C23—H23C	109.5
C14—C13—H13A	120.2	H23A—C23—H23C	109.5
O4—C14—C13	123.23 (12)	H23B—C23—H23C	109.5
O4—C14—C9	115.98 (11)	C21—C24—H24A	109.5
C13—C14—C9	120.78 (12)	C21—C24—H24B	109.5
O4—C15—C16	111.40 (11)	H24A—C24—H24B	109.5
O4—C15—H15A	109.3	C21—C24—H24C	109.5
C16—C15—H15A	109.3	H24A—C24—H24C	109.5
O4—C15—H15B	109.3	H24B—C24—H24C	109.5
C17—O1—C1—O2	5.8 (2)	C8—C9—C10—C11	177.90 (12)
C17—O1—C1—C2	−176.69 (10)	C9—C10—C11—C12	0.5 (2)
C3—O3—C2—C1	63.42 (14)	C10—C11—C12—C13	−1.0 (2)
O2—C1—C2—O3	−168.21 (12)	C11—C12—C13—C14	0.4 (2)
O1—C1—C2—O3	14.12 (15)	C15—O4—C14—C13	9.65 (18)
C2—O3—C3—C4	20.01 (17)	C15—O4—C14—C9	−171.68 (11)
C2—O3—C3—C8	−160.90 (11)	C12—C13—C14—O4	179.23 (13)
O3—C3—C4—C5	179.27 (12)	C12—C13—C14—C9	0.6 (2)
C8—C3—C4—C5	0.22 (19)	C10—C9—C14—O4	−179.80 (11)
C3—C4—C5—C6	−1.2 (2)	C8—C9—C14—O4	2.91 (17)
C4—C5—C6—C7	0.8 (2)	C10—C9—C14—C13	−1.10 (19)
C5—C6—C7—C8	0.5 (2)	C8—C9—C14—C13	−178.39 (12)
C6—C7—C8—C3	−1.45 (19)	C14—O4—C15—C16	67.83 (14)
C6—C7—C8—C9	174.84 (12)	C21—O6—C16—O5	1.3 (2)
O3—C3—C8—C7	−178.03 (11)	C21—O6—C16—C15	−176.87 (11)
C4—C3—C8—C7	1.08 (18)	O4—C15—C16—O5	21.25 (18)
O3—C3—C8—C9	5.71 (17)	O4—C15—C16—O6	−160.51 (11)
C4—C3—C8—C9	−175.19 (11)	C1—O1—C17—C20	−66.57 (16)
C7—C8—C9—C10	−125.19 (13)	C1—O1—C17—C18	174.98 (14)
C3—C8—C9—C10	50.96 (17)	C1—O1—C17—C19	57.41 (17)
C7—C8—C9—C14	52.05 (17)	C16—O6—C21—C23	−179.93 (12)
C3—C8—C9—C14	−131.80 (13)	C16—O6—C21—C22	−61.94 (16)
C14—C9—C10—C11	0.54 (19)	C16—O6—C21—C24	62.58 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2i	0.99	2.51	3.482 (2)	166
C20—H20C···O5ii	0.98	2.47	3.414 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O2i	0.99	2.51	3.482 (2)	166
C20—H20C⋯O5ii	0.98	2.47	3.414 (2)	162

Symmetry codes: (i) ; (ii) .