Diethyl 2,2'-(ethane-1,2-diyldi-oxy)di-benzo-ate.

The mol-ecular title compound, C20H22O6, was obtained by the reaction of ethyl 2-hy-droxy-benzoate with 1,2-di-chloro-ethane. The mol-ecule lies on a twofold rotation axis which passes through the middle of the central ethyl-ene bridge. This group exhibits a gauche conformation with the corresponding O-C-C-O torsion angle being 73.2 (2)°. The C atoms of the carboxyl group, the aryl and the O-CH2 group are coplanar, with an r.m.s. deviation of 0.01 Å. The two aryl rings form a dihedral angle of 67.94 (4)°. The ester ethyl group is disordered over two sets of sites with an occupancy ratio of 0.59 (2):0.41 (2). The crystal packing is dominated by van der Waals forces.

Related literature

For synthesis and structures of diesters, see: Ma et al. (2012 ▶); Hou & Kan (2007 ▶). For properties and applications of diesters, see: Chen & Liu (2002 ▶). For the synthesis of the title compound, see: Ma & Liu (2002 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For background to the applications of organic acids and esters, see: Chanthapally et al. (2012 ▶); Yan et al. (2012 ▶).

Experimental

Crystal data

C20H22O6

M = 358.38

Orthorhombic,

a = 21.805 (4) Å

b = 9.871 (2) Å

c = 8.8646 (18) Å

V = 1908.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.35 × 0.31 × 0.28 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.858, T max = 1.000

11280 measured reflections

2192 independent reflections

1543 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.132

S = 1.04

2192 reflections

140 parameters

24 restraints

H-atom parameters constrained

Δρmax = 0.17 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, dierster-0. DOI: 10.1107/S1600536814007673/wm5015sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007673/wm5015Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814007673/wm5015Isup3.cml

CCDC reference: 995747

Additional supporting information: crystallographic information; 3D view; checkCIF report

C20H22O6	F(000) = 760
Mr = 358.38	Dx = 1.248 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 11280 reflections
a = 21.805 (4) Å	θ = 1.9–27.6°
b = 9.871 (2) Å	µ = 0.09 mm−1
c = 8.8646 (18) Å	T = 298 K
V = 1908.0 (6) Å3	Prism, colourless
Z = 4	0.35 × 0.31 × 0.28 mm

Bruker SMART CCD diffractometer	2192 independent reflections
Radiation source: fine-focus sealed tube	1543 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 0 pixels mm-1	θmax = 27.6°, θmin = 1.9°
phi and ω scans	h = −28→27
Absorption correction: multi-scan (SADABS; Bruker, 2002)	k = −10→12
Tmin = 0.858, Tmax = 1.000	l = −10→11
11280 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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.132	w = 1/[σ2(Fo2) + (0.0606P)2 + 0.335P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2192 reflections	Δρmax = 0.17 e Å−3
140 parameters	Δρmin = −0.14 e Å−3
24 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0102 (19)

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	Occ. (<1)
O1	0.36609 (7)	0.94335 (11)	0.09160 (14)	0.0784 (4)
O2	0.41410 (7)	0.77861 (13)	−0.03024 (15)	0.0880 (5)
O3	0.43658 (5)	0.59258 (11)	0.20505 (13)	0.0632 (3)
C1	0.38057 (7)	0.81417 (15)	0.06775 (17)	0.0570 (4)
C02A	0.3859 (9)	1.0477 (15)	−0.0051 (11)	0.075 (3)	0.41 (2)
H02A	0.4024	1.0099	−0.0976	0.090*	0.41 (2)
H02B	0.3518	1.1066	−0.0307	0.090*	0.41 (2)
C02B	0.4008 (7)	1.0397 (13)	−0.0105 (13)	0.114 (4)	0.59 (2)
H02C	0.4421	1.0064	−0.0273	0.137*	0.59 (2)
H02D	0.3804	1.0466	−0.1074	0.137*	0.59 (2)
C2	0.34747 (7)	0.72278 (14)	0.17329 (15)	0.0522 (4)
C01A	0.4309 (8)	1.120 (2)	0.0708 (15)	0.127 (4)	0.41 (2)
H01A	0.4127	1.1683	0.1536	0.191*	0.41 (2)
H01B	0.4497	1.1835	0.0029	0.191*	0.41 (2)
H01C	0.4614	1.0587	0.1084	0.191*	0.41 (2)
C01B	0.4030 (7)	1.1719 (7)	0.0618 (8)	0.119 (3)	0.59 (2)
H01D	0.3620	1.2059	0.0738	0.179*	0.59 (2)
H01E	0.4262	1.2333	0.0004	0.179*	0.59 (2)
H01F	0.4220	1.1637	0.1590	0.179*	0.59 (2)
C3	0.28631 (8)	0.74645 (17)	0.20651 (18)	0.0654 (4)
H3A	0.2668	0.8215	0.1650	0.078*
C4	0.25382 (8)	0.6610 (2)	0.3000 (2)	0.0766 (5)
H4A	0.2126	0.6773	0.3198	0.092*
C5	0.28283 (8)	0.55161 (18)	0.3634 (2)	0.0730 (5)
H5A	0.2611	0.4946	0.4275	0.088*
C6	0.34359 (7)	0.52495 (15)	0.33381 (19)	0.0634 (4)
H6A	0.3627	0.4505	0.3778	0.076*
C7	0.37642 (7)	0.60994 (14)	0.23769 (16)	0.0518 (4)
C8	0.46777 (7)	0.48215 (15)	0.27597 (19)	0.0609 (4)
H8A	0.4482	0.3972	0.2493	0.073*
H8B	0.4662	0.4922	0.3848	0.073*

	U11	U22	U33	U12	U13	U23
O1	0.1251 (11)	0.0471 (6)	0.0631 (7)	0.0001 (6)	0.0089 (7)	0.0031 (5)
O2	0.1222 (11)	0.0685 (8)	0.0732 (8)	0.0098 (7)	0.0363 (8)	0.0084 (6)
O3	0.0597 (6)	0.0607 (6)	0.0692 (7)	0.0009 (5)	0.0008 (5)	0.0183 (5)
C1	0.0753 (9)	0.0505 (8)	0.0451 (7)	0.0019 (7)	−0.0047 (7)	−0.0018 (6)
C02A	0.128 (7)	0.054 (4)	0.043 (3)	−0.014 (4)	−0.014 (4)	0.008 (3)
C02B	0.174 (9)	0.065 (4)	0.104 (6)	−0.006 (4)	0.034 (5)	0.020 (4)
C2	0.0654 (9)	0.0485 (7)	0.0425 (7)	−0.0015 (6)	−0.0024 (6)	−0.0060 (6)
C01A	0.146 (10)	0.103 (9)	0.133 (7)	−0.059 (7)	0.022 (6)	0.010 (7)
C01B	0.228 (10)	0.057 (3)	0.073 (3)	−0.031 (4)	−0.001 (4)	0.003 (2)
C3	0.0717 (10)	0.0647 (9)	0.0597 (9)	0.0118 (8)	0.0008 (8)	−0.0057 (8)
C4	0.0655 (10)	0.0869 (12)	0.0774 (12)	−0.0004 (9)	0.0129 (9)	−0.0070 (10)
C5	0.0767 (11)	0.0687 (10)	0.0735 (11)	−0.0147 (9)	0.0173 (9)	0.0001 (9)
C6	0.0733 (10)	0.0530 (8)	0.0640 (9)	−0.0065 (7)	0.0039 (8)	0.0054 (7)
C7	0.0580 (8)	0.0487 (7)	0.0488 (8)	−0.0043 (6)	−0.0011 (6)	−0.0018 (6)
C8	0.0677 (8)	0.0487 (8)	0.0662 (9)	−0.0034 (7)	−0.0087 (7)	0.0060 (7)

O1—C1	1.3306 (18)	C01A—H01B	0.9600
O1—C02A	1.408 (14)	C01A—H01C	0.9600
O1—C02B	1.516 (14)	C01B—H01D	0.9600
O2—C1	1.1884 (19)	C01B—H01E	0.9600
O3—C7	1.3541 (18)	C01B—H01F	0.9600
O3—C8	1.4304 (17)	C3—C4	1.379 (2)
C1—C2	1.487 (2)	C3—H3A	0.9300
C02A—C01A	1.39 (2)	C4—C5	1.372 (3)
C02A—H02A	0.9700	C4—H4A	0.9300
C02A—H02B	0.9700	C5—C6	1.376 (2)
C02B—C01B	1.455 (15)	C5—H5A	0.9300
C02B—H02C	0.9700	C6—C7	1.394 (2)
C02B—H02D	0.9700	C6—H6A	0.9300
C2—C3	1.386 (2)	C8—C8i	1.479 (3)
C2—C7	1.402 (2)	C8—H8A	0.9700
C01A—H01A	0.9600	C8—H8B	0.9700
C1—O1—C02A	122.1 (7)	C02B—C01B—H01F	109.5
C1—O1—C02B	112.8 (5)	H01D—C01B—H01F	109.5
C02A—O1—C02B	12.6 (12)	H01E—C01B—H01F	109.5
C7—O3—C8	117.59 (11)	C4—C3—C2	121.27 (16)
O2—C1—O1	123.04 (15)	C4—C3—H3A	119.4
O2—C1—C2	125.41 (14)	C2—C3—H3A	119.4
O1—C1—C2	111.49 (13)	C5—C4—C3	119.41 (16)
C01A—C02A—O1	107.4 (10)	C5—C4—H4A	120.3
C01A—C02A—H02A	110.2	C3—C4—H4A	120.3
O1—C02A—H02A	110.2	C4—C5—C6	121.09 (16)
C01A—C02A—H02B	110.2	C4—C5—H5A	119.5
O1—C02A—H02B	110.2	C6—C5—H5A	119.5
H02A—C02A—H02B	108.5	C5—C6—C7	119.74 (15)
C01B—C02B—O1	108.4 (10)	C5—C6—H6A	120.1
C01B—C02B—H02C	110.0	C7—C6—H6A	120.1
O1—C02B—H02C	110.0	O3—C7—C6	123.51 (13)
C01B—C02B—H02D	110.0	O3—C7—C2	116.73 (12)
O1—C02B—H02D	110.0	C6—C7—C2	119.73 (14)
H02C—C02B—H02D	108.4	O3—C8—C8i	108.37 (12)
C3—C2—C7	118.74 (14)	O3—C8—H8A	110.0
C3—C2—C1	119.91 (13)	C8i—C8—H8A	110.0
C7—C2—C1	121.32 (13)	O3—C8—H8B	110.0
C02B—C01B—H01D	109.5	C8i—C8—H8B	110.0
C02B—C01B—H01E	109.5	H8A—C8—H8B	108.4
H01D—C01B—H01E	109.5
C02A—O1—C1—O2	4.9 (7)	C1—C2—C3—C4	177.81 (15)
C02B—O1—C1—O2	−4.7 (6)	C2—C3—C4—C5	1.1 (3)
C02A—O1—C1—C2	−172.4 (7)	C3—C4—C5—C6	−0.8 (3)
C02B—O1—C1—C2	177.9 (6)	C4—C5—C6—C7	−0.1 (3)
C1—O1—C02A—C01A	−107.6 (14)	C8—O3—C7—C6	−1.2 (2)
C02B—O1—C02A—C01A	−63 (4)	C8—O3—C7—C2	176.78 (13)
C1—O1—C02B—C01B	−156.1 (10)	C5—C6—C7—O3	178.61 (15)
C02A—O1—C02B—C01B	64 (4)	C5—C6—C7—C2	0.7 (2)
O2—C1—C2—C3	−136.02 (18)	C3—C2—C7—O3	−178.45 (13)
O1—C1—C2—C3	41.24 (19)	C1—C2—C7—O3	3.3 (2)
O2—C1—C2—C7	42.3 (2)	C3—C2—C7—C6	−0.4 (2)
O1—C1—C2—C7	−140.48 (14)	C1—C2—C7—C6	−178.72 (13)
C7—C2—C3—C4	−0.5 (2)	C7—O3—C8—C8i	179.76 (14)