Diethyl 4,4'-(3,6-dioxaoctane-1,8-diyl-dioxy)dibenzoate.

The title compound, C(24)H(30)O(8), was obtained by reaction of ethyl 4-hy-droxy-benzoate with 1,2-dichloro-ethane. The mol-ecule occupies a crystallographic inversion center, with its central ethyl-ene bridge in an anti conformation. The other ethyl-ene bridge has a gauche conformation, with the corresponding O-C-C-O torsion angle being 74.2 (1)°. The benzene rings are almost coplanar with the adjacent eth-oxy-carbonyl groups, with an r.m.s. deviation of 0.078 Å.

Related literature

For the synthesis, structures and applications of diesters, see Hou & Kan (2007 ▶); Tashiro et al. (1990 ▶); Zhang et al. (2007 ▶). For binding properties and applications of diesters, see: Chen & Liu (2002 ▶). For the synthesis of the title compound, see: Ma & Liu (2002 ▶); Ma & Cao (2011 ▶); Ma & Yang, (2011 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C24H30O8

M = 446.48

Monoclinic,

a = 9.2471 (17) Å

b = 12.530 (2) Å

c = 13.275 (2) Å

β = 131.528 (10)°

V = 1151.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.46 × 0.41 × 0.39 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.957, T max = 0.963

16767 measured reflections

5154 independent reflections

2879 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.164

S = 1.05

5154 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2001 ▶); 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812004874/ld2043sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004874/ld2043Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004874/ld2043Isup3.cml

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

C24H30O8	F(000) = 476
Mr = 446.48	Dx = 1.288 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16767 reflections
a = 9.2471 (17) Å	θ = 2.6–35.5°
b = 12.530 (2) Å	µ = 0.10 mm−1
c = 13.275 (2) Å	T = 298 K
β = 131.528 (10)°	Prism, colorless
V = 1151.5 (3) Å3	0.46 × 0.41 × 0.39 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	5154 independent reflections
Radiation source: fine-focus sealed tube	2879 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.028
Detector resolution: 0 pixels mm-1	θmax = 35.5°, θmin = 2.6°
phi and ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −20→20
Tmin = 0.957, Tmax = 0.963	l = −21→20
16767 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0674P)2 + 0.1605P] where P = (Fo2 + 2Fc2)/3
5154 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.23 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	−0.82218 (13)	0.56947 (7)	−0.25960 (9)	0.0452 (2)
O2	−0.61141 (15)	0.54988 (8)	−0.28929 (11)	0.0530 (3)
O3	−0.42322 (12)	0.15018 (7)	0.07878 (8)	0.0403 (2)
O4	−0.11518 (12)	0.04803 (7)	0.33477 (8)	0.0406 (2)
C1	−0.68021 (16)	0.51813 (9)	−0.24305 (12)	0.0374 (2)
C2	−0.61826 (15)	0.41940 (9)	−0.16212 (11)	0.0341 (2)
C3	−0.68284 (16)	0.39335 (10)	−0.09580 (12)	0.0379 (2)
H3A	−0.7724	0.4370	−0.1051	0.045*
C4	−0.61502 (17)	0.30326 (10)	−0.01627 (12)	0.0392 (3)
H4A	−0.6582	0.2868	0.0283	0.047*
C5	−0.48191 (15)	0.23687 (9)	−0.00255 (11)	0.0332 (2)
C6	−0.41928 (18)	0.26088 (10)	−0.07013 (13)	0.0418 (3)
H6A	−0.3329	0.2159	−0.0631	0.050*
C7	−0.48635 (18)	0.35259 (10)	−0.14845 (13)	0.0421 (3)
H7A	−0.4423	0.3695	−0.1923	0.051*
C8	−0.27474 (17)	0.08362 (10)	0.10606 (11)	0.0384 (2)
H8A	−0.1616	0.1261	0.1424	0.046*
H8B	−0.3199	0.0500	0.0237	0.046*
C9	−0.22479 (18)	0.00033 (10)	0.20575 (11)	0.0399 (3)
H9A	−0.3420	−0.0305	0.1791	0.048*
H9B	−0.1505	−0.0563	0.2086	0.048*
C10	−0.06051 (19)	−0.02821 (10)	0.43318 (12)	0.0441 (3)
H10A	0.0132	−0.0852	0.4361	0.053*
H10B	−0.1743	−0.0590	0.4119	0.053*
C11	−0.8867 (2)	0.67038 (10)	−0.33238 (13)	0.0460 (3)
H1	−0.7765	0.7084	−0.3088	0.055*
H2	−0.9433	0.7141	−0.3060	0.055*
C12	−1.0324 (2)	0.65276 (11)	−0.48130 (15)	0.0538 (3)
H3	−1.0756	0.7204	−0.5266	0.081*
H4	−1.1405	0.6140	−0.5046	0.081*
H5	−0.9745	0.6126	−0.5082	0.081*

	U11	U22	U33	U12	U13	U23
O1	0.0496 (5)	0.0386 (4)	0.0516 (5)	0.0099 (4)	0.0354 (5)	0.0108 (4)
O2	0.0629 (6)	0.0488 (5)	0.0639 (6)	0.0099 (4)	0.0490 (6)	0.0171 (4)
O3	0.0443 (4)	0.0400 (4)	0.0390 (4)	0.0081 (3)	0.0286 (4)	0.0109 (3)
O4	0.0449 (4)	0.0384 (4)	0.0283 (4)	−0.0018 (3)	0.0200 (4)	0.0060 (3)
C1	0.0387 (5)	0.0340 (5)	0.0365 (6)	0.0004 (4)	0.0237 (5)	0.0012 (4)
C2	0.0342 (5)	0.0336 (5)	0.0318 (5)	−0.0002 (4)	0.0207 (5)	0.0015 (4)
C3	0.0350 (5)	0.0391 (6)	0.0418 (6)	0.0050 (4)	0.0265 (5)	0.0048 (5)
C4	0.0398 (6)	0.0429 (6)	0.0419 (6)	0.0015 (5)	0.0301 (5)	0.0058 (5)
C5	0.0337 (5)	0.0334 (5)	0.0279 (5)	−0.0001 (4)	0.0184 (4)	0.0018 (4)
C6	0.0493 (6)	0.0420 (6)	0.0451 (6)	0.0120 (5)	0.0359 (6)	0.0090 (5)
C7	0.0505 (7)	0.0439 (6)	0.0438 (6)	0.0073 (5)	0.0362 (6)	0.0085 (5)
C8	0.0412 (6)	0.0407 (6)	0.0307 (5)	0.0063 (5)	0.0227 (5)	0.0054 (4)
C9	0.0435 (6)	0.0361 (6)	0.0325 (5)	0.0030 (5)	0.0220 (5)	0.0029 (4)
C10	0.0472 (6)	0.0412 (6)	0.0331 (6)	−0.0003 (5)	0.0220 (5)	0.0096 (5)
C11	0.0531 (7)	0.0315 (6)	0.0506 (7)	0.0063 (5)	0.0333 (6)	0.0033 (5)
C12	0.0563 (8)	0.0441 (7)	0.0519 (8)	0.0086 (6)	0.0320 (7)	0.0073 (6)

O1—C1	1.3428 (14)	C6—H6A	0.9300
O1—C11	1.4573 (15)	C7—H7A	0.9300
O2—C1	1.2072 (14)	C8—C9	1.4978 (16)
O3—C5	1.3650 (13)	C8—H8A	0.9700
O3—C8	1.4327 (14)	C8—H8B	0.9700
O4—C10	1.4140 (13)	C9—H9A	0.9700
O4—C9	1.4199 (14)	C9—H9B	0.9700
C1—C2	1.4821 (15)	C10—C10i	1.506 (3)
C2—C7	1.3886 (16)	C10—H10A	0.9700
C2—C3	1.3912 (16)	C10—H10B	0.9700
C3—C4	1.3800 (16)	C11—C12	1.497 (2)
C3—H3A	0.9300	C11—H1	0.9700
C4—C5	1.3939 (16)	C11—H2	0.9700
C4—H4A	0.9300	C12—H3	0.9600
C5—C6	1.3856 (15)	C12—H4	0.9600
C6—C7	1.3896 (17)	C12—H5	0.9600
C1—O1—C11	116.75 (10)	O3—C8—H8B	110.1
C5—O3—C8	118.36 (9)	C9—C8—H8B	110.1
C10—O4—C9	111.23 (9)	H8A—C8—H8B	108.4
O2—C1—O1	123.13 (11)	O4—C9—C8	109.14 (10)
O2—C1—C2	124.26 (11)	O4—C9—H9A	109.9
O1—C1—C2	112.62 (10)	C8—C9—H9A	109.9
C7—C2—C3	118.97 (10)	O4—C9—H9B	109.9
C7—C2—C1	118.80 (10)	C8—C9—H9B	109.9
C3—C2—C1	122.19 (10)	H9A—C9—H9B	108.3
C4—C3—C2	120.53 (10)	O4—C10—C10i	107.61 (12)
C4—C3—H3A	119.7	O4—C10—H10A	110.2
C2—C3—H3A	119.7	C10i—C10—H10A	110.2
C3—C4—C5	120.15 (10)	O4—C10—H10B	110.2
C3—C4—H4A	119.9	C10i—C10—H10B	110.2
C5—C4—H4A	119.9	H10A—C10—H10B	108.5
O3—C5—C6	124.56 (10)	O1—C11—C12	111.23 (11)
O3—C5—C4	115.59 (9)	O1—C11—H1	109.4
C6—C5—C4	119.85 (10)	C12—C11—H1	109.4
C5—C6—C7	119.55 (10)	O1—C11—H2	109.4
C5—C6—H6A	120.2	C12—C11—H2	109.4
C7—C6—H6A	120.2	H1—C11—H2	108.0
C2—C7—C6	120.93 (10)	C11—C12—H3	109.5
C2—C7—H7A	119.5	C11—C12—H4	109.5
C6—C7—H7A	119.5	H3—C12—H4	109.5
O3—C8—C9	108.14 (9)	C11—C12—H5	109.5
O3—C8—H8A	110.1	H3—C12—H5	109.5
C9—C8—H8A	110.1	H4—C12—H5	109.5
C11—O1—C1—O2	−2.72 (18)	C3—C4—C5—C6	−0.70 (18)
C11—O1—C1—C2	177.11 (10)	O3—C5—C6—C7	−178.83 (11)
O2—C1—C2—C7	−6.63 (18)	C4—C5—C6—C7	1.60 (19)
O1—C1—C2—C7	173.54 (10)	C3—C2—C7—C6	0.10 (19)
O2—C1—C2—C3	171.16 (12)	C1—C2—C7—C6	177.96 (11)
O1—C1—C2—C3	−8.67 (16)	C5—C6—C7—C2	−1.3 (2)
C7—C2—C3—C4	0.82 (18)	C5—O3—C8—C9	175.32 (9)
C1—C2—C3—C4	−176.96 (11)	C10—O4—C9—C8	−178.60 (10)
C2—C3—C4—C5	−0.53 (18)	O3—C8—C9—O4	−74.22 (12)
C8—O3—C5—C6	5.50 (17)	C9—O4—C10—C10i	177.97 (13)
C8—O3—C5—C4	−174.91 (10)	C1—O1—C11—C12	83.70 (14)
C3—C4—C5—O3	179.70 (10)