Home Crystal structure of dimethyl 4,4′-oxydibenzoate, C16H14O5
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Crystal structure of dimethyl 4,4′-oxydibenzoate, C16H14O5

  • Lindley Maxweel , Alejandro Cárdenas and Iván Brito EMAIL logo
Published/Copyright: August 23, 2018

Abstract

C16H14O5, Aba2 (no. 41), a = 7.4156(5) Å, b = 31.415(2) Å, c = 5.9451(4) Å, V = 1384.98(16) Å3, Z = 4, Rgt(F) = 0.0316, wRref(F2) = 0.0924, T = 297(2) K.

CCDC no.: 1860152

The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Crystal collection and handling.

Crystal:Block, colorless
Size:0.18 × 0.16 × 0.10 mm
Wavelength:Mo Kα radiation (λ = 0.71073 Å)
μ:0.103 mm−1
Diffractometer, scan mode:Bruker AXS D8-Venture, Φ and ω-scans
θmax, completeness:28.8°, >99%
N(hkl)measured, N(hkl)unique, Rint:10890, 1707, 0.0208
Criterion for Iobs, N(hkl)gt:Iobs > 2σ(Iobs), 1548
N(param)refined:110
Programs:Bruker programs [1], OLEX2 [2], SHELX [3]
Table 2:

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

AtomxyzUiso*/Ueq
O10.5000000.5000000.8451(3)0.0401(4)
O20.5665(3)0.30641(5)0.5562(3)0.0725(6)
O30.4337(2)0.33366(4)0.2516(3)0.0546(4)
C10.4965(2)0.38021(5)0.5510(3)0.0338(4)
C20.5763(3)0.38758(5)0.7590(3)0.0385(4)
H20.630(3)0.3643(7)0.831(4)0.046
C30.5804(2)0.42817(6)0.8493(3)0.0364(4)
H30.639(3)0.4346(6)0.987(4)0.044
C40.5010(2)0.46144(5)0.7330(3)0.0311(4)
C50.4171(2)0.45463(6)0.5270(3)0.0341(4)
H50.363(3)0.4772(7)0.440(4)0.041
C60.4161(2)0.41393(5)0.4364(3)0.0341(4)
H60.359(3)0.4083(7)0.298(4)0.041
C70.5025(3)0.33624(6)0.4581(3)0.0418(5)
C80.4431(4)0.29212(8)0.1454(5)0.0672(7)
H8A0.4134610.294748−0.0111250.101
H8B0.3591170.2731960.2168420.101
H8C0.5629980.2809340.1603780.101

Source of material

In a vial flask, 11 mg (0.048 mmol) of Zn(AcO)2 ⋅ H2O was dissolved in 0.5 mL of MeOH while in another vial flask 20 mg (0.048 mmol) of the compound C24H18N4O3 previously reported [4] was dissolved in 0.5 mL of CH2Cl2. The resulting solutions were mixture in a 5 mL vial flask and 1 mL of DMSO was added. The flask was sealed and heated at 110 °C per 48 h. Finally, the mixture was cooled gradually, obtaining a big colorless single crystal.

FT-IR (KBr pellet, cm−1): 2958 (vw), 3014 (vw), ν(C—H aryl), 2958 (vw), 2843 (vw), ν(C—H alkyl), 1720 (vs) ν(C = O), 1284 (s) ν(C—O), 1108 (s), δ(C—O), 767(s) δ(C—H). 1H NMR (300 MHz, Acetone-d6) δ 8.07 (d, J = 8.9 Hz, 4H), 7.18 (d, J = 8.9 Hz, 4H), 3.88 (s, 6H).

Experimental details

H atoms were located in the difference Fourier map, but refined with fixed individual displacement parameters, using a riding model with C—H distances 0.96 Å for CH3 with U(H) values of 1.5Ueq(C). The other H atoms were free refined with distances in the range of 0.94(3)–0.96(3) Å (for aromatic rings with 1.2Ueq(C)). The Flack-Parsons parameter isn’t conclusive.

Discussion

This paper forms part of our continuing study of the synthesis and structural characterization of a flexible ligand for preparation of coordination polymers [5 and references therein]. The title compound was isolated during attempts to synthesize a coordination polymer between 4,4′-oxybis[N-(pyridin-4-yl)benzamide] trihydrate a flexible ligand reported for us [4] and Zn(AcO)2 ⋅ H2O salt.

There is one half of the title molecule in the asymmetric unit (cf. the figure; i = 1 − x, 1 − y, z). The O1 atom lies on two fold axis. The angles between the planes defined by C1/C2/C3/C4/C5/C6 (plane 1); C4/O1/C4i (plane 2); and C1i/C2i/C3i/C4i/C5i/C6i (plane 3) are 29.75(12)° for the planes 1 & 2 and 55.15(8)° for the planes 1 & 3. The aromatic ether bond lengths and angle are 1.3827(18) Å and 122.37(19)° respectively, which is consistent with those found in similar compounds [6]. All the other distances and angles are normal. The crystal structure is stabilized by van der Waals interaction only. Actually, a plausible reaction mechanism of the title compound is under study.

Acknowledgements

IB Thanks to Fondecyt grant 1170256 and Fondequip Program, grant EQM130021.

References

Bruker. APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA (2007).Search in Google Scholar

Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H.: OLEX2 a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 42 (2009) 339–341.10.1107/S0021889808042726Search in Google Scholar

Sheldrick, G. M.: SHELXT – Integrated space-group and crystal-structure determination and Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053273314026370Search in Google Scholar

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Received: 2018-05-08
Accepted: 2018-08-03
Published Online: 2018-08-23
Published in Print: 2018-11-27

©2018 Lindley Maxweel et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

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