Diethyl 4,4'-(ethane-1,2-diyldi-oxy)dibenzoate.

The title compound, C(20)H(22)O(6), was obtained by the reaction of ethyl 4-hy-droxy-benzoate with 1,2-dichloro-ethane in dimethyl-formamide. The mol-ecule lies around the crystallographic inversion center at (0,0,0), with the asymmetric unit consisting of one half of the mol-ecule. The two ethyl groups are in trans positions. The ethyl, carboxyl, aryl and O-CH(2) groups are coplanar with an r.m.s. deviation of 0.0208 (9) Å. The whole mol-ecule is planar with an r.m.s. deviation of 0.0238 (9) Å for the 19 atoms used in the calculation and 0.0071 (9) Å for the two aryl groups in the mol-ecule. A weak inter-molecular C-H⋯O hydrogen bond and a C-H⋯π inter-action help to consolidate the three-dimensional network.

Related literature

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

Experimental

Crystal data

C20H22O6

M = 358.38

Monoclinic,

a = 4.8504 (10) Å

b = 15.847 (3) Å

c = 12.0159 (19) Å

β = 104.250 (8)°

V = 895.2 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.49 × 0.35 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.960, T max = 0.979

8592 measured reflections

1980 independent reflections

1713 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.130

S = 1.02

1980 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.34 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: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811021258/ez2245sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021258/ez2245Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811021258/ez2245Isup3.cml

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

C20H22O6	F(000) = 380
Mr = 358.38	Dx = 1.330 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8592 reflections
a = 4.8504 (10) Å	θ = 2.2–27.2°
b = 15.847 (3) Å	µ = 0.10 mm−1
c = 12.0159 (19) Å	T = 298 K
β = 104.250 (8)°	Prism, colorless
V = 895.2 (3) Å3	0.49 × 0.35 × 0.22 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	1980 independent reflections
Radiation source: fine-focus sealed tube	1713 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 0 pixels mm-1	θmax = 27.2°, θmin = 2.2°
φ and ω scans	h = −6→5
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −20→20
Tmin = 0.960, Tmax = 0.979	l = −15→14
8592 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) = 0.130	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0876P)2 + 0.1852P] where P = (Fo2 + 2Fc2)/3
1980 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.34 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	−1.19587 (17)	0.35479 (5)	−0.09590 (7)	0.0219 (2)
O2	−0.9567 (2)	0.37413 (6)	0.08774 (8)	0.0313 (3)
O3	−0.30202 (17)	0.06258 (5)	−0.06554 (7)	0.0209 (2)
C1	−1.5949 (3)	0.43801 (8)	−0.19241 (11)	0.0302 (3)
H1A	−1.7199	0.4833	−0.1843	0.045*
H1B	−1.7026	0.3869	−0.2106	0.045*
H1C	−1.5046	0.4510	−0.2530	0.045*
C2	−1.3723 (3)	0.42675 (7)	−0.08179 (11)	0.0234 (3)
H2A	−1.2566	0.4772	−0.0643	0.028*
H2B	−1.4617	0.4164	−0.0192	0.028*
C3	−0.9916 (2)	0.33543 (7)	−0.00155 (10)	0.0199 (3)
C4	−0.8119 (2)	0.26316 (7)	−0.01966 (10)	0.0188 (3)
C5	−0.8593 (2)	0.21922 (7)	−0.12413 (10)	0.0199 (3)
H5A	−1.0097	0.2346	−0.1851	0.024*
C6	−0.6832 (2)	0.15314 (7)	−0.13669 (10)	0.0196 (3)
H6A	−0.7145	0.1243	−0.2060	0.024*
C7	−0.4580 (2)	0.12990 (7)	−0.04481 (10)	0.0174 (3)
C8	−0.4063 (2)	0.17353 (7)	0.05940 (10)	0.0197 (3)
H8A	−0.2549	0.1584	0.1201	0.024*
C9	−0.5851 (2)	0.23998 (7)	0.07089 (10)	0.0197 (3)
H9A	−0.5526	0.2693	0.1400	0.024*
C10	−0.0671 (2)	0.03624 (7)	0.02485 (9)	0.0182 (3)
H10A	−0.1317	0.0179	0.0912	0.022*
H10B	0.0678	0.0820	0.0478	0.022*

	U11	U22	U33	U12	U13	U23
O1	0.0219 (4)	0.0201 (4)	0.0220 (4)	0.0073 (3)	0.0025 (3)	−0.0001 (3)
O2	0.0341 (5)	0.0299 (5)	0.0257 (5)	0.0111 (4)	−0.0005 (4)	−0.0075 (4)
O3	0.0185 (4)	0.0204 (4)	0.0212 (4)	0.0056 (3)	0.0002 (3)	−0.0036 (3)
C1	0.0313 (7)	0.0299 (7)	0.0275 (7)	0.0108 (5)	0.0034 (5)	0.0042 (5)
C2	0.0235 (6)	0.0183 (5)	0.0281 (6)	0.0065 (4)	0.0058 (5)	−0.0008 (4)
C3	0.0199 (6)	0.0182 (5)	0.0209 (6)	0.0009 (4)	0.0040 (4)	0.0011 (4)
C4	0.0188 (6)	0.0169 (5)	0.0210 (6)	0.0006 (4)	0.0053 (4)	0.0014 (4)
C5	0.0198 (6)	0.0192 (5)	0.0194 (6)	0.0013 (4)	0.0025 (4)	0.0023 (4)
C6	0.0217 (6)	0.0190 (5)	0.0176 (5)	−0.0001 (4)	0.0036 (4)	−0.0007 (4)
C7	0.0163 (5)	0.0154 (5)	0.0210 (6)	0.0002 (4)	0.0053 (4)	0.0007 (4)
C8	0.0176 (5)	0.0200 (5)	0.0200 (6)	0.0009 (4)	0.0019 (4)	0.0004 (4)
C9	0.0208 (6)	0.0186 (5)	0.0191 (6)	−0.0001 (4)	0.0039 (4)	−0.0022 (4)
C10	0.0158 (5)	0.0176 (5)	0.0200 (5)	0.0017 (4)	0.0021 (4)	−0.0008 (4)

O1—C3	1.3446 (14)	C4—C5	1.4040 (16)
O1—C2	1.4604 (13)	C5—C6	1.3829 (15)
O2—C3	1.2109 (15)	C5—H5A	0.9300
O3—C7	1.3659 (13)	C6—C7	1.3977 (16)
O3—C10	1.4294 (13)	C6—H6A	0.9300
C1—C2	1.5027 (18)	C7—C8	1.3978 (16)
C1—H1A	0.9600	C8—C9	1.3925 (16)
C1—H1B	0.9600	C8—H8A	0.9300
C1—H1C	0.9600	C9—H9A	0.9300
C2—H2A	0.9700	C10—C10i	1.513 (2)
C2—H2B	0.9700	C10—H10A	0.9700
C3—C4	1.4874 (15)	C10—H10B	0.9700
C4—C9	1.3928 (16)
C3—O1—C2	114.29 (9)	C6—C5—H5A	119.9
C7—O3—C10	117.60 (8)	C4—C5—H5A	119.9
C2—C1—H1A	109.5	C5—C6—C7	119.79 (10)
C2—C1—H1B	109.5	C5—C6—H6A	120.1
H1A—C1—H1B	109.5	C7—C6—H6A	120.1
C2—C1—H1C	109.5	O3—C7—C6	114.96 (10)
H1A—C1—H1C	109.5	O3—C7—C8	124.36 (10)
H1B—C1—H1C	109.5	C6—C7—C8	120.68 (10)
O1—C2—C1	107.71 (10)	C9—C8—C7	118.94 (11)
O1—C2—H2A	110.2	C9—C8—H8A	120.5
C1—C2—H2A	110.2	C7—C8—H8A	120.5
O1—C2—H2B	110.2	C8—C9—C4	120.89 (10)
C1—C2—H2B	110.2	C8—C9—H9A	119.6
H2A—C2—H2B	108.5	C4—C9—H9A	119.6
O2—C3—O1	123.03 (10)	O3—C10—C10i	105.17 (11)
O2—C3—C4	124.07 (11)	O3—C10—H10A	110.7
O1—C3—C4	112.89 (10)	C10i—C10—H10A	110.7
C9—C4—C5	119.45 (10)	O3—C10—H10B	110.7
C9—C4—C3	117.87 (10)	C10i—C10—H10B	110.7
C5—C4—C3	122.68 (11)	H10A—C10—H10B	108.8
C6—C5—C4	120.23 (11)
C3—O1—C2—C1	−177.91 (10)	C10—O3—C7—C6	179.46 (9)
C2—O1—C3—O2	0.12 (16)	C10—O3—C7—C8	−1.26 (16)
C2—O1—C3—C4	−178.70 (9)	C5—C6—C7—O3	178.44 (9)
O2—C3—C4—C9	−1.66 (17)	C5—C6—C7—C8	−0.88 (16)
O1—C3—C4—C9	177.15 (9)	O3—C7—C8—C9	−178.42 (10)
O2—C3—C4—C5	179.57 (11)	C6—C7—C8—C9	0.83 (16)
O1—C3—C4—C5	−1.62 (16)	C7—C8—C9—C4	−0.16 (16)
C9—C4—C5—C6	0.41 (16)	C5—C4—C9—C8	−0.45 (16)
C3—C4—C5—C6	179.16 (10)	C3—C4—C9—C8	−179.26 (10)
C4—C5—C6—C7	0.25 (16)	C7—O3—C10—C10i	−178.04 (10)

Cg is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O2ii	0.93	2.47	3.2784 (16)	146.
C10—H10B···Cgiii	0.97	2.65	3.741 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O2i	0.93	2.47	3.2784 (16)	146
C10—H10B⋯Cgii	0.97	2.65	3.741 (2)	143

Symmetry codes: (i) ; (ii) .