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In the title compound, C16H14O4, the dihedral angle between the two aromatic rings is 75.8 (1)°. The torsion angle about the central C—C bond is 77.2 (3)°. The packing of the mol­ecules in the solid state is stabilized by C—H...O, C—H...π and π–π intermolecular interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803009942/ww6078sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803009942/ww6078Isup2.hkl
Contains datablock I

CCDC reference: 214828

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.086
  • wR factor = 0.240
  • Data-to-parameter ratio = 17.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

Polyether compounds are of much recent interest due to their remarkable metal ion selectivity, ability to transport alkali metal ion through biological and artificial membranes and their utilization to organic synthetic procedures (Armstrong & Lindoy, 1975; Grimsley et al., 1977).

The bond lengths and angles of the title compound, (I), agree with the values reported for 2,2'-[1,2-ethanediylbis(oxy)](benzenemethanol) (Bailey et al., 1989). The dihedral angle between the phenyl rings A (C2–C7) and B (C10–C15) is 75.9 (1)°. Atoms O1/C1/O2/C8 and atoms O4/C16/O3/C9 lie almost on their respective phenyl ring planes [the deviations of the above atoms are 0.020 (3), 0.058 (4), −0.010 (2) and −0.040 (4) Å, and −0.101 (4), −0.030 (5), 0.050 (3) and 0.012 (4) Å, respectively]. The methylene group between the phenyl rings has the gauche form and the torsion angle about the C8—C9 bond is 77.2 (4)°, so the molecule is twisted.

The molecules are linked by weak C—H···O interactions and form an infinite chain running along the a direction (Fig. 2). The face-to-face interactions are between A and Aiv, and B and Bv, which stack in the lattice along b and a axis, respectively, with centroid–centroid distances of 3.784 (2) and 3.731 (2) Å, respectively [symmetry codes: (iv) 1 − x, 1 − y, −z; (v) −x, 2 − y, 1 − z]. Apart from these weak ππ interactions, the packing of the molecules in the solid state is stabilized by C—H···O and C—H···π intermolecular interactions (Table 2).

Experimental top

1,2-Dibromoethane (9.396 g, 0.05 mol) in methanol (10 ml) was added to salicylaldehyde (9.052 g, 0.1 mol) in methanol (30 ml) and the solution was heated. Sodium hydroxide pellets (4 g, 0.1 mol) in water (15 ml) was added and the reaction mixture was refluxed under N2 atmosphere for nearly 48 h. Then the resulting solution was allowed to cool at room temperature (298 K). The solid obtained was filtered and washed with water and methanol. The crystals were obtained by recrystallization from chloroform.

Refinement top

All the H atoms were geometrically positioned and were treated as riding on their parent atoms, with C—H distances in the range 0.93–0.97 Å.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. The molecular structure, with the atom-numbering scheme. Ellipsoids are drawn at the 35% probability level.
[Figure 2] Fig. 2. A packing diagram of the molecule, viewed down the a axis. ππ and C—H···O interactions are indicated by dashed lines.
3,4:9,10-dibenzo-1,12-diformyl-5,8-dioxododecane top
Crystal data top
C16H14O4Z = 2
Mr = 270.27F(000) = 284
Triclinic, P1Dx = 1.334 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.7956 (7) ÅCell parameters from 1815 reflections
b = 8.4511 (8) Åθ = 1.8–28.3°
c = 11.4697 (11) ŵ = 0.10 mm1
α = 83.054 (2)°T = 293 K
β = 75.008 (2)°Block, yellow
γ = 67.219 (2)°0.36 × 0.24 × 0.16 mm
V = 672.80 (11) Å3
Data collection top
Siemens SMART CCD area-detector
diffractometer
1273 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.064
Graphite monochromatorθmax = 28.3°, θmin = 1.8°
ω scansh = 109
4829 measured reflectionsk = 1011
3172 independent reflectionsl = 1515
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.086H-atom parameters constrained
wR(F2) = 0.240 w = 1/[σ2(Fo2) + (0.1202P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.83(Δ/σ)max < 0.001
3172 reflectionsΔρmax = 0.37 e Å3
182 parametersΔρmin = 0.38 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.036 (10)
Crystal data top
C16H14O4γ = 67.219 (2)°
Mr = 270.27V = 672.80 (11) Å3
Triclinic, P1Z = 2
a = 7.7956 (7) ÅMo Kα radiation
b = 8.4511 (8) ŵ = 0.10 mm1
c = 11.4697 (11) ÅT = 293 K
α = 83.054 (2)°0.36 × 0.24 × 0.16 mm
β = 75.008 (2)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
1273 reflections with I > 2σ(I)
4829 measured reflectionsRint = 0.064
3172 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0860 restraints
wR(F2) = 0.240H-atom parameters constrained
S = 0.83Δρmax = 0.37 e Å3
3172 reflectionsΔρmin = 0.38 e Å3
182 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
xyzUiso*/Ueq
O10.0784 (4)0.7888 (4)0.0461 (2)0.0759 (9)
O20.4719 (3)0.8211 (3)0.09749 (19)0.0488 (7)
O30.4016 (3)0.8694 (3)0.35573 (18)0.0482 (7)
O40.2152 (5)0.5866 (4)0.6190 (3)0.0837 (10)
C10.2041 (5)0.7996 (5)0.0087 (3)0.0537 (10)
H10.16780.86580.05890.064*
C20.4092 (5)0.7172 (4)0.0607 (3)0.0412 (8)
C30.4717 (5)0.6241 (4)0.1657 (3)0.0512 (9)
H30.38310.61140.20090.061*
C40.6634 (6)0.5510 (5)0.2176 (3)0.0598 (10)
H40.70470.48980.28820.072*
C50.7954 (5)0.5688 (5)0.1642 (3)0.0568 (10)
H50.92510.51980.20010.068*
C60.7384 (5)0.6571 (4)0.0596 (3)0.0471 (9)
H60.82840.66810.02470.056*
C70.5440 (4)0.7302 (4)0.0063 (3)0.0385 (8)
C80.6004 (5)0.8395 (5)0.1585 (3)0.0501 (9)
H8A0.68900.88420.10310.060*
H8B0.67340.72890.19000.060*
C90.4851 (5)0.9606 (5)0.2593 (3)0.0494 (9)
H9A0.56631.00360.28680.059*
H9B0.38561.05740.23210.059*
C100.2935 (4)0.9571 (4)0.4586 (3)0.0396 (8)
C110.2198 (5)0.8611 (4)0.5527 (3)0.0426 (8)
C120.1026 (5)0.9452 (5)0.6585 (3)0.0537 (9)
H120.05240.88380.72150.064*
C130.0600 (6)1.1148 (5)0.6716 (3)0.0606 (10)
H130.02021.16910.74230.073*
C140.1370 (6)1.2064 (5)0.5788 (3)0.0598 (10)
H140.11071.32180.58830.072*
C150.2512 (5)1.1281 (5)0.4734 (3)0.0498 (9)
H150.30061.19120.41140.060*
C160.2658 (6)0.6784 (5)0.5405 (3)0.0594 (10)
H160.33950.62930.46690.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0534 (17)0.103 (2)0.087 (2)0.0422 (17)0.0279 (15)0.0081 (17)
O20.0387 (13)0.0626 (16)0.0484 (13)0.0209 (11)0.0072 (11)0.0129 (12)
O30.0607 (15)0.0429 (14)0.0437 (13)0.0250 (12)0.0075 (12)0.0010 (11)
O40.115 (3)0.0615 (19)0.083 (2)0.0504 (19)0.0168 (18)0.0162 (16)
C10.048 (2)0.070 (3)0.048 (2)0.0315 (19)0.0087 (18)0.0065 (19)
C20.0451 (19)0.0428 (19)0.0406 (17)0.0235 (15)0.0097 (15)0.0056 (15)
C30.064 (2)0.048 (2)0.052 (2)0.0286 (19)0.0203 (19)0.0044 (18)
C40.077 (3)0.053 (2)0.046 (2)0.026 (2)0.004 (2)0.0108 (18)
C50.050 (2)0.054 (2)0.055 (2)0.0159 (18)0.0041 (18)0.0071 (18)
C60.042 (2)0.050 (2)0.052 (2)0.0220 (16)0.0084 (17)0.0016 (17)
C70.0402 (19)0.0394 (18)0.0359 (16)0.0181 (14)0.0039 (15)0.0003 (15)
C80.0418 (19)0.065 (2)0.050 (2)0.0265 (17)0.0120 (17)0.0013 (18)
C90.052 (2)0.056 (2)0.0446 (18)0.0286 (18)0.0079 (17)0.0022 (17)
C100.0429 (18)0.042 (2)0.0403 (17)0.0176 (15)0.0173 (15)0.0030 (15)
C110.049 (2)0.044 (2)0.0434 (18)0.0225 (16)0.0198 (16)0.0065 (16)
C120.057 (2)0.064 (3)0.0440 (19)0.0267 (19)0.0128 (18)0.0022 (18)
C130.068 (3)0.058 (3)0.051 (2)0.020 (2)0.0053 (19)0.014 (2)
C140.075 (3)0.050 (2)0.060 (2)0.025 (2)0.020 (2)0.005 (2)
C150.060 (2)0.046 (2)0.049 (2)0.0254 (18)0.0153 (18)0.0005 (17)
C160.071 (3)0.055 (2)0.058 (2)0.028 (2)0.018 (2)0.003 (2)
Geometric parameters (Å, º) top
O1—C11.204 (4)C8—C91.493 (4)
O2—C71.365 (3)C8—H8A0.9700
O2—C81.423 (3)C8—H8B0.9700
O3—C101.365 (4)C9—H9A0.9700
O3—C91.432 (3)C9—H9B0.9700
O4—C161.205 (4)C10—C151.374 (4)
C1—C21.464 (5)C10—C111.408 (4)
C1—H10.9300C11—C121.394 (5)
C2—C31.391 (4)C11—C161.459 (5)
C2—C71.397 (4)C12—C131.358 (5)
C3—C41.372 (5)C12—H120.9300
C3—H30.9300C13—C141.386 (5)
C4—C51.387 (5)C13—H130.9300
C4—H40.9300C14—C151.368 (5)
C5—C61.370 (4)C14—H140.9300
C5—H50.9300C15—H150.9300
C6—C71.393 (4)C16—H160.9300
C6—H60.9300
C7—O2—C8119.2 (2)H8A—C8—H8B108.4
C10—O3—C9117.3 (2)O3—C9—C8108.1 (3)
O1—C1—C2125.5 (4)O3—C9—H9A110.1
O1—C1—H1117.2C8—C9—H9A110.1
C2—C1—H1117.2O3—C9—H9B110.1
C3—C2—C7119.3 (3)C8—C9—H9B110.1
C3—C2—C1119.8 (3)H9A—C9—H9B108.4
C7—C2—C1121.0 (3)O3—C10—C15124.7 (3)
C4—C3—C2120.4 (3)O3—C10—C11115.4 (3)
C4—C3—H3119.8C15—C10—C11119.8 (3)
C2—C3—H3119.8C12—C11—C10118.1 (3)
C3—C4—C5119.7 (3)C12—C11—C16120.8 (3)
C3—C4—H4120.2C10—C11—C16121.1 (3)
C5—C4—H4120.2C13—C12—C11121.5 (3)
C6—C5—C4121.3 (3)C13—C12—H12119.2
C6—C5—H5119.3C11—C12—H12119.2
C4—C5—H5119.3C12—C13—C14119.5 (4)
C5—C6—C7119.1 (3)C12—C13—H13120.2
C5—C6—H6120.5C14—C13—H13120.2
C7—C6—H6120.5C15—C14—C13120.4 (3)
O2—C7—C6123.9 (3)C15—C14—H14119.8
O2—C7—C2115.9 (3)C13—C14—H14119.8
C6—C7—C2120.2 (3)C14—C15—C10120.6 (3)
O2—C8—C9108.0 (3)C14—C15—H15119.7
O2—C8—H8A110.1C10—C15—H15119.7
C9—C8—H8A110.1O4—C16—C11124.7 (4)
O2—C8—H8B110.1O4—C16—H16117.6
C9—C8—H8B110.1C11—C16—H16117.6
O1—C1—C2—C33.4 (5)O2—C8—C9—O377.2 (3)
O1—C1—C2—C7176.4 (3)C9—O3—C10—C153.6 (4)
C7—C2—C3—C42.3 (5)C9—O3—C10—C11177.8 (2)
C1—C2—C3—C4177.9 (3)O3—C10—C11—C12177.7 (3)
C2—C3—C4—C50.6 (5)C15—C10—C11—C120.9 (4)
C3—C4—C5—C60.5 (5)O3—C10—C11—C162.8 (4)
C4—C5—C6—C70.0 (5)C15—C10—C11—C16178.6 (3)
C8—O2—C7—C62.1 (4)C10—C11—C12—C130.2 (5)
C8—O2—C7—C2179.8 (3)C16—C11—C12—C13179.3 (3)
C5—C6—C7—O2179.8 (3)C11—C12—C13—C141.1 (5)
C5—C6—C7—C21.7 (5)C12—C13—C14—C151.6 (6)
C3—C2—C7—O2178.9 (3)C13—C14—C15—C100.9 (5)
C1—C2—C7—O20.9 (4)O3—C10—C15—C14178.1 (3)
C3—C2—C7—C62.9 (5)C11—C10—C15—C140.4 (5)
C1—C2—C7—C6177.3 (3)C12—C11—C16—O43.0 (6)
C7—O2—C8—C9173.3 (3)C10—C11—C16—O4176.5 (3)
C10—O3—C9—C8178.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O20.932.402.746 (4)102
C16—H16···O30.932.412.748 (4)102
C6—H6···O1i0.932.483.290 (4)146
C9—H9A···CgBii0.972.843.712 (2)150
C9—H9B···CgAiii0.972.763.473 (2)131
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+2, z+1; (iii) x+1, y+2, z.

Experimental details

Crystal data
Chemical formulaC16H14O4
Mr270.27
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.7956 (7), 8.4511 (8), 11.4697 (11)
α, β, γ (°)83.054 (2), 75.008 (2), 67.219 (2)
V3)672.80 (11)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.36 × 0.24 × 0.16
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4829, 3172, 1273
Rint0.064
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.086, 0.240, 0.83
No. of reflections3172
No. of parameters182
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.38

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990), SHELXL97 and PARST (Nardelli, 1995).

Selected geometric parameters (Å, º) top
O1—C11.204 (4)O4—C161.205 (4)
O2—C71.365 (3)C1—C21.464 (5)
O2—C81.423 (3)C8—C91.493 (4)
O3—C101.365 (4)C11—C161.459 (5)
O3—C91.432 (3)
C7—O2—C8119.2 (2)O2—C8—C9108.0 (3)
C10—O3—C9117.3 (2)O3—C9—C8108.1 (3)
O1—C1—C2125.5 (4)O3—C10—C15124.7 (3)
O2—C7—C6123.9 (3)O3—C10—C11115.4 (3)
O2—C7—C2115.9 (3)O4—C16—C11124.7 (4)
O1—C1—C2—C33.4 (5)O2—C8—C9—O377.2 (3)
C7—O2—C8—C9173.3 (3)C12—C11—C16—O43.0 (6)
C10—O3—C9—C8178.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O20.932.402.746 (4)102
C16—H16···O30.932.412.748 (4)102
C6—H6···O1i0.932.483.290 (4)146
C9—H9A···CgBii0.972.843.712 (2)150
C9—H9B···CgAiii0.972.763.473 (2)131
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+2, z+1; (iii) x+1, y+2, z.
 

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