Diethyl 2,2'-(biphenyl-2,2'-diyldi-oxy)diacetate.

In the title compound, C(20)H(22)O(6), the mean planes through the benzene rings make a dihedral angle of 59.82 (7)° with each other. Weak inter-molecular C-H⋯O inter-actions together with π-π stacking inter-actions [centroid-centroid distance = 3.830 (1) Å] between benzene rings are observed in the crystal packing.

Related literature

For related structures, see: Rabnawaz et al. (2008 ▶); Ali et al. (2008 ▶); Ibad et al. (2008 ▶).

Experimental

Crystal data

C20H22O6

M = 358.38

Triclinic,

a = 7.4683 (13) Å

b = 10.8189 (15) Å

c = 12.050 (2) Å

α = 104.733 (17)°

β = 95.05 (2)°

γ = 106.897 (14)°

V = 887.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 153 K

0.58 × 0.53 × 0.24 mm

Data collection

Rigaku AFC-8S diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.945, T max = 0.977

6640 measured reflections

3104 independent reflections

2787 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.099

S = 1.04

3104 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.18 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/S1600536810026863/ez2221sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026863/ez2221Isup2.hkl

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

C20H22O6	Z = 2
Mr = 358.38	F(000) = 380
Triclinic, P1	Dx = 1.342 Mg m−3
a = 7.4683 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.8189 (15) Å	Cell parameters from 2971 reflections
c = 12.050 (2) Å	θ = 3.1–26.3°
α = 104.733 (17)°	µ = 0.10 mm−1
β = 95.05 (2)°	T = 153 K
γ = 106.897 (14)°	Chip, colorless
V = 887.1 (3) Å3	0.58 × 0.53 × 0.24 mm

Rigaku AFC-8S diffractometer	3104 independent reflections
Radiation source: normal-focus sealed tube	2787 reflections with I > 2σ(I)
graphite	Rint = 0.014
Detector resolution: 14.6306 pixels mm-1	θmax = 25.1°, θmin = 3.1°
ω scans	h = −8→8
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −12→12
Tmin = 0.945, Tmax = 0.977	l = −14→12
6640 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0493P)2 + 0.3462P] where P = (Fo2 + 2Fc2)/3
3104 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.26152 (13)	0.49153 (10)	−0.09823 (8)	0.0281 (2)
O2	0.10844 (14)	0.63977 (10)	−0.03410 (9)	0.0289 (3)
O3	0.37964 (13)	0.73993 (9)	0.17431 (8)	0.0229 (2)
O4	0.64269 (14)	1.13019 (10)	0.42800 (8)	0.0270 (2)
O5	0.71807 (19)	1.39716 (12)	0.43450 (10)	0.0455 (3)
O6	0.74896 (14)	1.45726 (9)	0.62997 (8)	0.0284 (2)
C1	0.2426 (2)	0.36891 (16)	−0.29568 (13)	0.0315 (3)
H1A	0.1754	0.3436	−0.3759	0.047*
H1B	0.2329	0.2872	−0.2723	0.047*
H1C	0.3768	0.4191	−0.2912	0.047*
C2	0.1555 (2)	0.45549 (19)	−0.21611 (13)	0.0407 (4)
H2A	0.1631	0.5380	−0.2395	0.049*
H2B	0.0201	0.4056	−0.2194	0.049*
C3	0.22147 (18)	0.58407 (13)	−0.01637 (12)	0.0213 (3)
C4	0.33426 (18)	0.60535 (13)	0.10190 (11)	0.0218 (3)
H4A	0.2593	0.5424	0.1406	0.026*
H4B	0.4532	0.5843	0.0911	0.026*
C5	0.50568 (17)	0.83979 (13)	0.14036 (11)	0.0197 (3)
C6	0.51573 (18)	0.97228 (13)	0.19636 (11)	0.0196 (3)
C7	0.64460 (19)	1.07739 (13)	0.16831 (12)	0.0239 (3)
H7A	0.6553	1.1682	0.2068	0.029*
C8	0.75716 (19)	1.05198 (14)	0.08549 (12)	0.0261 (3)
H8A	0.8428	1.1247	0.0667	0.031*
C9	0.74388 (19)	0.92018 (15)	0.03053 (12)	0.0267 (3)
H9A	0.8203	0.9023	−0.0266	0.032*
C10	0.61985 (19)	0.81358 (14)	0.05811 (12)	0.0244 (3)
H10A	0.6129	0.7232	0.0210	0.029*
C11	0.38246 (18)	1.00240 (13)	0.27616 (11)	0.0207 (3)
C12	0.18639 (19)	0.95132 (13)	0.23529 (12)	0.0242 (3)
H12A	0.1391	0.8899	0.1593	0.029*
C13	0.0593 (2)	0.98855 (14)	0.30363 (13)	0.0277 (3)
H13A	−0.0734	0.9537	0.2745	0.033*
C14	0.1289 (2)	1.07714 (14)	0.41479 (13)	0.0297 (3)
H14A	0.0430	1.1041	0.4615	0.036*
C15	0.3225 (2)	1.12712 (14)	0.45896 (13)	0.0281 (3)
H15A	0.3685	1.1868	0.5358	0.034*
C16	0.44882 (19)	1.08923 (13)	0.39009 (12)	0.0223 (3)
C17	0.7184 (2)	1.23201 (14)	0.53605 (12)	0.0284 (3)
H17A	0.8479	1.2336	0.5641	0.034*
H17B	0.6384	1.2107	0.5943	0.034*
C18	0.72672 (19)	1.36982 (14)	0.52501 (12)	0.0263 (3)
C19	0.7734 (2)	1.59703 (14)	0.63189 (14)	0.0349 (4)
H19A	0.6748	1.5994	0.5726	0.042*
H19B	0.8998	1.6391	0.6141	0.042*
C20	0.7560 (2)	1.67243 (15)	0.75077 (14)	0.0352 (4)
H20A	0.7719	1.7665	0.7541	0.053*
H20B	0.8544	1.6699	0.8088	0.053*
H20C	0.6303	1.6303	0.7674	0.053*

	U11	U22	U33	U12	U13	U23
O1	0.0283 (5)	0.0326 (6)	0.0214 (5)	0.0160 (4)	0.0003 (4)	−0.0010 (4)
O2	0.0284 (5)	0.0264 (5)	0.0338 (6)	0.0133 (4)	0.0033 (4)	0.0075 (4)
O3	0.0279 (5)	0.0169 (5)	0.0224 (5)	0.0059 (4)	0.0092 (4)	0.0032 (4)
O4	0.0303 (5)	0.0263 (5)	0.0210 (5)	0.0131 (4)	0.0000 (4)	−0.0019 (4)
O5	0.0766 (9)	0.0358 (6)	0.0258 (6)	0.0188 (6)	0.0108 (6)	0.0107 (5)
O6	0.0422 (6)	0.0211 (5)	0.0213 (5)	0.0123 (4)	0.0035 (4)	0.0036 (4)
C1	0.0309 (7)	0.0337 (8)	0.0238 (8)	0.0074 (6)	0.0037 (6)	0.0020 (6)
C2	0.0376 (8)	0.0587 (11)	0.0225 (8)	0.0246 (8)	−0.0030 (6)	−0.0013 (7)
C3	0.0195 (6)	0.0172 (6)	0.0270 (7)	0.0054 (5)	0.0068 (5)	0.0058 (5)
C4	0.0249 (7)	0.0167 (6)	0.0235 (7)	0.0077 (5)	0.0054 (5)	0.0039 (5)
C5	0.0204 (6)	0.0194 (6)	0.0174 (6)	0.0047 (5)	0.0021 (5)	0.0046 (5)
C6	0.0210 (6)	0.0202 (6)	0.0170 (6)	0.0075 (5)	0.0013 (5)	0.0041 (5)
C7	0.0269 (7)	0.0203 (7)	0.0225 (7)	0.0067 (5)	0.0021 (5)	0.0047 (5)
C8	0.0241 (7)	0.0269 (7)	0.0254 (7)	0.0039 (5)	0.0052 (5)	0.0093 (6)
C9	0.0247 (7)	0.0315 (7)	0.0212 (7)	0.0068 (6)	0.0082 (5)	0.0044 (6)
C10	0.0257 (7)	0.0221 (7)	0.0219 (7)	0.0071 (5)	0.0053 (5)	0.0008 (5)
C11	0.0265 (7)	0.0172 (6)	0.0212 (7)	0.0094 (5)	0.0063 (5)	0.0072 (5)
C12	0.0288 (7)	0.0193 (6)	0.0265 (7)	0.0088 (5)	0.0067 (6)	0.0085 (5)
C13	0.0268 (7)	0.0240 (7)	0.0373 (8)	0.0098 (6)	0.0119 (6)	0.0138 (6)
C14	0.0370 (8)	0.0264 (7)	0.0356 (8)	0.0171 (6)	0.0198 (6)	0.0138 (6)
C15	0.0399 (8)	0.0242 (7)	0.0241 (7)	0.0153 (6)	0.0117 (6)	0.0063 (6)
C16	0.0290 (7)	0.0189 (6)	0.0217 (7)	0.0110 (5)	0.0054 (5)	0.0067 (5)
C17	0.0362 (8)	0.0254 (7)	0.0206 (7)	0.0137 (6)	−0.0020 (6)	0.0000 (6)
C18	0.0289 (7)	0.0281 (7)	0.0200 (7)	0.0096 (6)	0.0026 (5)	0.0040 (6)
C19	0.0524 (9)	0.0208 (7)	0.0330 (9)	0.0128 (7)	0.0078 (7)	0.0094 (6)
C20	0.0516 (9)	0.0201 (7)	0.0318 (8)	0.0105 (7)	0.0062 (7)	0.0056 (6)

O1—C3	1.3374 (16)	C8—C9	1.381 (2)
O1—C2	1.4618 (18)	C8—H8A	0.9500
O2—C3	1.2044 (16)	C9—C10	1.388 (2)
O3—C5	1.3864 (16)	C9—H9A	0.9500
O3—C4	1.4181 (16)	C10—H10A	0.9500
O4—C16	1.3816 (17)	C11—C12	1.399 (2)
O4—C17	1.4167 (17)	C11—C16	1.402 (2)
O5—C18	1.2017 (18)	C12—C13	1.3900 (19)
O6—C18	1.3362 (17)	C12—H12A	0.9500
O6—C19	1.4634 (17)	C13—C14	1.385 (2)
C1—C2	1.492 (2)	C13—H13A	0.9500
C1—H1A	0.9800	C14—C15	1.389 (2)
C1—H1B	0.9800	C14—H14A	0.9500
C1—H1C	0.9800	C15—C16	1.3913 (19)
C2—H2A	0.9900	C15—H15A	0.9500
C2—H2B	0.9900	C17—C18	1.514 (2)
C3—C4	1.5175 (19)	C17—H17A	0.9900
C4—H4A	0.9900	C17—H17B	0.9900
C4—H4B	0.9900	C19—C20	1.495 (2)
C5—C10	1.3916 (18)	C19—H19A	0.9900
C5—C6	1.3971 (18)	C19—H19B	0.9900
C6—C7	1.3966 (19)	C20—H20A	0.9800
C6—C11	1.4897 (18)	C20—H20B	0.9800
C7—C8	1.386 (2)	C20—H20C	0.9800
C7—H7A	0.9500
C3—O1—C2	116.34 (11)	C9—C10—H10A	120.2
C5—O3—C4	116.66 (10)	C5—C10—H10A	120.2
C16—O4—C17	117.43 (11)	C12—C11—C16	118.38 (12)
C18—O6—C19	115.91 (11)	C12—C11—C6	119.93 (12)
C2—C1—H1A	109.5	C16—C11—C6	121.54 (12)
C2—C1—H1B	109.5	C13—C12—C11	121.36 (13)
H1A—C1—H1B	109.5	C13—C12—H12A	119.3
C2—C1—H1C	109.5	C11—C12—H12A	119.3
H1A—C1—H1C	109.5	C14—C13—C12	119.08 (13)
H1B—C1—H1C	109.5	C14—C13—H13A	120.5
O1—C2—C1	107.38 (12)	C12—C13—H13A	120.5
O1—C2—H2A	110.2	C13—C14—C15	120.95 (13)
C1—C2—H2A	110.2	C13—C14—H14A	119.5
O1—C2—H2B	110.2	C15—C14—H14A	119.5
C1—C2—H2B	110.2	C14—C15—C16	119.63 (14)
H2A—C2—H2B	108.5	C14—C15—H15A	120.2
O2—C3—O1	124.57 (13)	C16—C15—H15A	120.2
O2—C3—C4	125.14 (12)	O4—C16—C15	123.64 (12)
O1—C3—C4	110.27 (11)	O4—C16—C11	115.79 (12)
O3—C4—C3	111.80 (11)	C15—C16—C11	120.56 (13)
O3—C4—H4A	109.3	O4—C17—C18	111.40 (12)
C3—C4—H4A	109.3	O4—C17—H17A	109.3
O3—C4—H4B	109.3	C18—C17—H17A	109.3
C3—C4—H4B	109.3	O4—C17—H17B	109.3
H4A—C4—H4B	107.9	C18—C17—H17B	109.3
O3—C5—C10	123.59 (12)	H17A—C17—H17B	108.0
O3—C5—C6	115.63 (11)	O5—C18—O6	124.81 (13)
C10—C5—C6	120.77 (12)	O5—C18—C17	124.61 (13)
C7—C6—C5	118.18 (12)	O6—C18—C17	110.57 (12)
C7—C6—C11	119.86 (12)	O6—C19—C20	108.07 (12)
C5—C6—C11	121.75 (12)	O6—C19—H19A	110.1
C8—C7—C6	121.36 (13)	C20—C19—H19A	110.1
C8—C7—H7A	119.3	O6—C19—H19B	110.1
C6—C7—H7A	119.3	C20—C19—H19B	110.1
C9—C8—C7	119.49 (13)	H19A—C19—H19B	108.4
C9—C8—H8A	120.3	C19—C20—H20A	109.5
C7—C8—H8A	120.3	C19—C20—H20B	109.5
C8—C9—C10	120.55 (13)	H20A—C20—H20B	109.5
C8—C9—H9A	119.7	C19—C20—H20C	109.5
C10—C9—H9A	119.7	H20A—C20—H20C	109.5
C9—C10—C5	119.64 (13)	H20B—C20—H20C	109.5
C3—O1—C2—C1	171.24 (12)	C7—C6—C11—C16	−58.95 (18)
C2—O1—C3—O2	−1.3 (2)	C5—C6—C11—C16	126.46 (14)
C2—O1—C3—C4	176.98 (12)	C16—C11—C12—C13	2.17 (19)
C5—O3—C4—C3	−67.26 (14)	C6—C11—C12—C13	−173.39 (12)
O2—C3—C4—O3	−33.27 (18)	C11—C12—C13—C14	−0.6 (2)
O1—C3—C4—O3	148.41 (11)	C12—C13—C14—C15	−1.0 (2)
C4—O3—C5—C10	−15.26 (18)	C13—C14—C15—C16	0.9 (2)
C4—O3—C5—C6	166.12 (11)	C17—O4—C16—C15	−9.89 (19)
O3—C5—C6—C7	178.06 (11)	C17—O4—C16—C11	171.55 (11)
C10—C5—C6—C7	−0.60 (19)	C14—C15—C16—O4	−177.75 (12)
O3—C5—C6—C11	−7.26 (18)	C14—C15—C16—C11	0.8 (2)
C10—C5—C6—C11	174.08 (12)	C12—C11—C16—O4	176.37 (11)
C5—C6—C7—C8	1.4 (2)	C6—C11—C16—O4	−8.15 (18)
C11—C6—C7—C8	−173.42 (12)	C12—C11—C16—C15	−2.24 (19)
C6—C7—C8—C9	−0.9 (2)	C6—C11—C16—C15	173.24 (12)
C7—C8—C9—C10	−0.4 (2)	C16—O4—C17—C18	−75.23 (15)
C8—C9—C10—C5	1.1 (2)	C19—O6—C18—O5	−3.1 (2)
O3—C5—C10—C9	−179.17 (12)	C19—O6—C18—C17	175.61 (12)
C6—C5—C10—C9	−0.6 (2)	O4—C17—C18—O5	−17.8 (2)
C7—C6—C11—C12	116.47 (14)	O4—C17—C18—O6	163.46 (11)
C5—C6—C11—C12	−58.13 (18)	C18—O6—C19—C20	168.59 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4b···O1i	0.99	2.50	3.472 (2)	167.7 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4b⋯O1i	0.99	2.50	3.472 (2)	168 (1)

Symmetry code: (i) .