1,2-Bis(2-meth­oxy-6-formyl­phen­oxy)ethane

Li, H.; Cai, L.; Chen, D.; Li, J.; Chen, Y.

doi:10.1107/S1600536810054085

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o306

doi:10.1107/S1600536810054085

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1,2-Bis(2-methoxy-6-formylphenoxy)ethane

Hongqi Li,^a ^* Li Cai,^a Dongling Chen,^a Jinxing Li ^a and Yijun Chen ^a

^aKey Laboratory of Science & Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering & Biotechnology, Donghua University, Shanghai 201620, People's Republic of China
^*Correspondence e-mail: hongqili@dhu.edu.cn

(Received 18 December 2010; accepted 24 December 2010; online 8 January 2011)

In the title compound [systematic name: 3,3′-dimethoxy-2,2′-(ethane-1,2-diyldioxy)dibenzaldehyde], C₁₈H₁₈O₆, prepared from 1,2-dibromoethane and ortho-vanillin in the presence of sodium carbonate, the two vanillin units are linked via a CH₂–CH₂ bridge. The two benzene rings are inclined at a dihedral angle of 41.6 (5)°.

Related literature

For the use of open chain-ionophores, including polyethylene glycols, as microbiological agents and in ion binding, see: Valeur et al. (1992 ); Tuncer & Erk (2000 ). For the synthesis, see: Tuncer & Erk (2000). For related structures, see: Higham et al. (2010 ).

Experimental

Crystal data

C₁₈H₁₈O₆
M_r = 330.32
Monoclinic, P 2₁ /n
a = 4.161 (3) Å
b = 30.155 (18) Å
c = 12.934 (8) Å
β = 96.817 (7)°
V = 1611.6 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.988, T_max = 0.992
14774 measured reflections
2815 independent reflections
1519 reflections with I > 2σ(I)
R_int = 0.096

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.141
S = 1.00
2815 reflections
220 parameters
H-atom parameters not refined
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810054085/sj5080sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054085/sj5080Isup2.hkl

checkCIF report

Comment top

Open chain ionophores including polyethylene glycols have proved to be extremely interesting compounds due to their versatility as microbiological agents and in ion binding (Valeur et al., 1992). Their extraordinary capacity for ion binding has attracted much attention in view of their acyclic and bulky structures. For example, aromatic carbonyl derivatives of glycols such as 1,2-bis(2-methoxy-6- formylphenoxy)ethane were investigated to determine the role of sodium ions using steady state fluorescence spectroscopy (Tuncer & Erk, 2000). 1,2-Bis(2-methoxy-6-formylphenoxy)ethane and its analogues have also been used in the synthesis of dienone-ether macrocycles displaying molecular and supramolecular diversity (Higham et al., 2010). Herein we present the single-crystal structure of the title compound.

Related literature top

For the use of open chain-ionophores, including polyethylene glycols, as microbiological agents and in ion binding, see: Valeur et al. (1992); Tuncer & Erk (2000). For the synthesis, see: Tuncer & Erk (2000). For related structures, see: Higham et al. (2010).

Experimental top

The title compound was prepared as reported in the literature (Tuncer & Erk, 2000). Single crystals suitable for X-ray diffraction measurement was obtained by slow evaporation of the solution in acetone [m.p. 391–393 K; literature value: 392 K (Tuncer & Erk, 2000)].

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

Fig. 1. A view of the molecule of the title compound. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

3,3'-Dimethoxy-2,2'-(ethane-1,2-diyldioxy)dibenzaldehyde top

Crystal data top

C₁₈H₁₈O₆	F(000) = 696
M_r = 330.32	D_x = 1.361 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 391–393 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 4.161 (3) Å	Cell parameters from 1432 reflections
b = 30.155 (18) Å	θ = 2.6–19.0°
c = 12.934 (8) Å	µ = 0.10 mm⁻¹
β = 96.817 (7)°	T = 296 K
V = 1611.6 (17) Å³	Block, colorless
Z = 4	0.12 × 0.10 × 0.08 mm

Data collection top

Bruker APEXII CCD diffractometer	2815 independent reflections
Radiation source: fine-focus sealed tube	1519 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.096
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −4→4
T_min = 0.988, T_max = 0.992	k = −35→35
14774 measured reflections	l = −15→15

Refinement top

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)] = 0.060	H-atom parameters not refined
wR(F²) = 0.141	w = 1/[σ²(F_o²) + (0.059P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
2815 reflections	Δρ_max = 0.18 e Å⁻³
220 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0130 (19)

Crystal data top

C₁₈H₁₈O₆	V = 1611.6 (17) Å³
M_r = 330.32	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.161 (3) Å	µ = 0.10 mm⁻¹
b = 30.155 (18) Å	T = 296 K
c = 12.934 (8) Å	0.12 × 0.10 × 0.08 mm
β = 96.817 (7)°

Data collection top

Bruker APEXII CCD diffractometer	2815 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	1519 reflections with I > 2σ(I)
T_min = 0.988, T_max = 0.992	R_int = 0.096
14774 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.141	H-atom parameters not refined
S = 1.00	Δρ_max = 0.18 e Å⁻³
2815 reflections	Δρ_min = −0.18 e Å⁻³
220 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.3389 (9)	0.03026 (11)	0.5936 (2)	0.0647 (10)
H1A	0.5683	0.0344	0.5956	0.097*
H1B	0.2895	−0.0008	0.5895	0.097*
H1C	0.2676	0.0424	0.6556	0.097*
C2	0.2236 (7)	0.09709 (10)	0.4969 (2)	0.0448 (8)
C3	0.4057 (8)	0.12260 (11)	0.5701 (2)	0.0554 (9)
H3	0.5160	0.1092	0.6286	0.066*
C4	0.4264 (8)	0.16785 (12)	0.5577 (3)	0.0622 (10)
H4	0.5543	0.1845	0.6071	0.075*
C5	0.2608 (8)	0.18851 (11)	0.4733 (3)	0.0547 (9)
H5	0.2717	0.2192	0.4666	0.066*
C6	0.0754 (7)	0.16342 (10)	0.3975 (2)	0.0453 (8)
C7	0.0586 (7)	0.11786 (10)	0.4081 (2)	0.0420 (8)
C8	−0.1070 (8)	0.18701 (12)	0.3090 (3)	0.0612 (10)
H8	−0.2209	0.1703	0.2564	0.073*
C9	0.0325 (8)	0.06410 (9)	0.2724 (2)	0.0461 (8)
H9A	−0.1130	0.0407	0.2449	0.055*
H9B	0.2118	0.0504	0.3156	0.055*
C10	0.1595 (7)	0.08728 (10)	0.1841 (2)	0.0438 (8)
H10A	0.2860	0.1129	0.2094	0.053*
H10B	0.2979	0.0675	0.1501	0.053*
C11	−0.0342 (7)	0.11450 (10)	0.0157 (2)	0.0440 (8)
C12	0.1182 (8)	0.15543 (11)	0.0050 (3)	0.0532 (9)
C13	0.1759 (9)	0.16920 (13)	−0.0933 (3)	0.0714 (11)
H13	0.2742	0.1965	−0.1016	0.086*
C14	0.0882 (11)	0.14262 (16)	−0.1793 (3)	0.0814 (13)
H14	0.1269	0.1523	−0.2450	0.098*
C15	−0.0523 (10)	0.10304 (14)	−0.1689 (3)	0.0747 (12)
H15	−0.1064	0.0854	−0.2274	0.090*
C16	−0.1190 (8)	0.08786 (11)	−0.0705 (2)	0.0526 (9)
C17	−0.2777 (9)	0.04495 (12)	−0.0610 (3)	0.0703 (11)
H17	−0.3183	0.0360	0.0050	0.084*
C18	0.3642 (9)	0.21970 (10)	0.0892 (3)	0.0809 (12)
H18A	0.5724	0.2134	0.0677	0.121*
H18B	0.3920	0.2335	0.1565	0.121*
H18C	0.2469	0.2393	0.0398	0.121*
O1	−0.1379 (5)	0.09317 (6)	0.33650 (14)	0.0448 (6)
O2	−0.1126 (5)	0.10109 (6)	0.11105 (14)	0.0446 (6)
O3	0.1872 (6)	0.17924 (7)	0.09468 (19)	0.0640 (7)
O4	0.1771 (5)	0.05236 (7)	0.50439 (15)	0.0560 (6)
O5	−0.1154 (7)	0.22701 (8)	0.30153 (19)	0.0849 (9)
O6	−0.3593 (8)	0.02042 (9)	−0.1333 (2)	0.1053 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.080 (3)	0.067 (2)	0.045 (2)	0.001 (2)	−0.0003 (19)	0.0127 (18)
C2	0.052 (2)	0.045 (2)	0.0370 (18)	−0.0069 (17)	0.0063 (15)	−0.0016 (16)
C3	0.059 (2)	0.066 (2)	0.039 (2)	−0.0036 (19)	−0.0018 (17)	−0.0019 (18)
C4	0.069 (3)	0.067 (3)	0.050 (2)	−0.018 (2)	0.0009 (19)	−0.0127 (19)
C5	0.060 (2)	0.047 (2)	0.058 (2)	−0.0068 (17)	0.0130 (19)	−0.0113 (18)
C6	0.050 (2)	0.044 (2)	0.043 (2)	0.0017 (16)	0.0124 (16)	−0.0041 (16)
C7	0.0433 (19)	0.050 (2)	0.0340 (18)	−0.0050 (16)	0.0084 (15)	−0.0083 (16)
C8	0.068 (2)	0.061 (3)	0.056 (2)	0.013 (2)	0.0077 (19)	−0.0067 (19)
C9	0.061 (2)	0.0381 (18)	0.0395 (18)	0.0023 (16)	0.0051 (16)	0.0010 (14)
C10	0.0451 (19)	0.0461 (19)	0.0399 (18)	0.0039 (15)	0.0038 (15)	0.0001 (15)
C11	0.0456 (19)	0.049 (2)	0.0382 (19)	0.0093 (16)	0.0081 (15)	0.0059 (16)
C12	0.053 (2)	0.055 (2)	0.053 (2)	0.0084 (18)	0.0105 (18)	0.0120 (18)
C13	0.070 (3)	0.072 (3)	0.076 (3)	0.010 (2)	0.024 (2)	0.032 (2)
C14	0.093 (3)	0.108 (4)	0.046 (3)	0.025 (3)	0.023 (2)	0.027 (3)
C15	0.088 (3)	0.094 (3)	0.042 (2)	0.026 (3)	0.006 (2)	0.001 (2)
C16	0.057 (2)	0.061 (2)	0.0390 (19)	0.0138 (18)	0.0035 (16)	0.0029 (18)
C17	0.082 (3)	0.062 (3)	0.064 (3)	0.008 (2)	−0.002 (2)	−0.014 (2)
C18	0.069 (3)	0.046 (2)	0.123 (3)	−0.009 (2)	−0.006 (2)	0.024 (2)
O1	0.0467 (13)	0.0490 (13)	0.0387 (12)	−0.0020 (11)	0.0051 (10)	−0.0055 (10)
O2	0.0433 (12)	0.0535 (14)	0.0371 (12)	0.0007 (10)	0.0055 (10)	0.0064 (10)
O3	0.0704 (16)	0.0468 (14)	0.0756 (18)	−0.0126 (12)	0.0120 (13)	0.0075 (13)
O4	0.0708 (16)	0.0526 (15)	0.0419 (13)	−0.0078 (12)	−0.0044 (11)	0.0059 (10)
O5	0.122 (2)	0.0432 (16)	0.086 (2)	0.0179 (15)	−0.0016 (16)	−0.0016 (13)
O6	0.138 (3)	0.083 (2)	0.089 (2)	0.0013 (18)	−0.012 (2)	−0.0349 (17)

Geometric parameters (Å, º) top

C1—O4	1.430 (3)	C10—O2	1.447 (3)
C1—H1A	0.9600	C10—H10A	0.9700
C1—H1B	0.9600	C10—H10B	0.9700
C1—H1C	0.9600	C11—O2	1.373 (3)
C2—O4	1.368 (4)	C11—C16	1.385 (4)
C2—C3	1.376 (4)	C11—C12	1.402 (4)
C2—C7	1.413 (4)	C12—O3	1.366 (4)
C3—C4	1.378 (4)	C12—C13	1.385 (4)
C3—H3	0.9300	C13—C14	1.384 (5)
C4—C5	1.369 (4)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.343 (5)
C5—C6	1.396 (4)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.412 (4)
C6—C7	1.383 (4)	C15—H15	0.9300
C6—C8	1.479 (4)	C16—C17	1.464 (5)
C7—O1	1.378 (3)	C17—O6	1.209 (4)
C8—O5	1.210 (4)	C17—H17	0.9300
C8—H8	0.9300	C18—O3	1.431 (3)
C9—O1	1.449 (3)	C18—H18A	0.9600
C9—C10	1.489 (4)	C18—H18B	0.9600
C9—H9A	0.9700	C18—H18C	0.9600
C9—H9B	0.9700

O4—C1—H1A	109.5	C9—C10—H10A	110.0
O4—C1—H1B	109.5	O2—C10—H10B	110.0
H1A—C1—H1B	109.5	C9—C10—H10B	110.0
O4—C1—H1C	109.5	H10A—C10—H10B	108.4
H1A—C1—H1C	109.5	O2—C11—C16	119.1 (3)
H1B—C1—H1C	109.5	O2—C11—C12	120.4 (3)
O4—C2—C3	125.0 (3)	C16—C11—C12	120.4 (3)
O4—C2—C7	115.8 (3)	O3—C12—C13	125.5 (3)
C3—C2—C7	119.1 (3)	O3—C12—C11	115.5 (3)
C2—C3—C4	120.7 (3)	C13—C12—C11	119.0 (3)
C2—C3—H3	119.7	C14—C13—C12	120.4 (4)
C4—C3—H3	119.7	C14—C13—H13	119.8
C5—C4—C3	120.7 (3)	C12—C13—H13	119.8
C5—C4—H4	119.6	C15—C14—C13	120.7 (4)
C3—C4—H4	119.6	C15—C14—H14	119.6
C4—C5—C6	119.8 (3)	C13—C14—H14	119.6
C4—C5—H5	120.1	C14—C15—C16	120.9 (4)
C6—C5—H5	120.1	C14—C15—H15	119.6
C7—C6—C5	120.0 (3)	C16—C15—H15	119.6
C7—C6—C8	121.8 (3)	C11—C16—C15	118.6 (3)
C5—C6—C8	118.2 (3)	C11—C16—C17	121.3 (3)
O1—C7—C6	120.2 (3)	C15—C16—C17	120.1 (3)
O1—C7—C2	119.9 (3)	O6—C17—C16	124.3 (4)
C6—C7—C2	119.7 (3)	O6—C17—H17	117.8
O5—C8—C6	123.2 (3)	C16—C17—H17	117.8
O5—C8—H8	118.4	O3—C18—H18A	109.5
C6—C8—H8	118.4	O3—C18—H18B	109.5
O1—C9—C10	113.4 (2)	H18A—C18—H18B	109.5
O1—C9—H9A	108.9	O3—C18—H18C	109.5
C10—C9—H9A	108.9	H18A—C18—H18C	109.5
O1—C9—H9B	108.9	H18B—C18—H18C	109.5
C10—C9—H9B	108.9	C7—O1—C9	114.8 (2)
H9A—C9—H9B	107.7	C11—O2—C10	114.8 (2)
O2—C10—C9	108.3 (2)	C12—O3—C18	117.6 (3)
O2—C10—H10A	110.0	C2—O4—C1	117.4 (2)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈O₆
M_r	330.32
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	4.161 (3), 30.155 (18), 12.934 (8)
β (°)	96.817 (7)
V (Å³)	1611.6 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.988, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	14774, 2815, 1519
R_int	0.096
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.141, 1.00
No. of reflections	2815
No. of parameters	220
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

Financial support of the project by the Shanghai Natural Science Foundation (No. 06ZR14001) is acknowledged.

References

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