Home The crystal structure of dimethyl 2,2ʹ-((adamantane-1,3-diylbis(4,1-phenylene)) bis(oxy))diacetate, C28H32O6
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The crystal structure of dimethyl 2,2ʹ-((adamantane-1,3-diylbis(4,1-phenylene)) bis(oxy))diacetate, C28H32O6

  • Xiao-Ming Chen and Fei Zeng ORCID logo EMAIL logo
Published/Copyright: May 18, 2023

Abstract

C28H32O6, orthorhombic, Pnma (no. 62), a = 7.752(2) Å, b = 29.959(8) Å, c = 10.176(3) Å, V = 2363.5(11) Å3, Z = 4, R gt(F) = 0.1145, wR ref(F 2) = 0.1076, T = 296(2) K.

CCDC No.: 2257342

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colourless block
Size: 0.20 × 0.20 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.09 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 27.5°, >99%
N(hkl) measured , N(hkl) unique, R int: 24647, 2751, 0.023
Criterion for I obs, N(hkl) gt: I obs > 2 σ(I obs), 2296
N(param)refined: 228
Programs: Bruker [1], SHELX [2]
Table 2:

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

Atom x y z U iso*/U eq
O1 0.03590 (12) 0.44545 (3) 0.08710 (10) 0.0484 (3)
O5 0.28535 (14) 0.50053 (4) −0.01515 (11) 0.0573 (3)
O10 0.26718 (15) 0.54521 (3) 0.16098 (11) 0.0584 (3)
C1 0.3625 (2) 0.250000 0.04604 (16) 0.0336 (3)
H1A 0.254 (3) 0.250000 −0.0149 (19) 0.039 (5)*
H1B 0.323 (3) 0.250000 0.137 (2) 0.044 (5)*
C2 0.46798 (15) 0.29276 (4) 0.02170 (11) 0.0347 (3)
C3 0.14691 (17) 0.40978 (4) 0.07906 (13) 0.0399 (3)
C4 0.7357 (2) 0.250000 0.08362 (18) 0.0420 (4)
H4 0.838 (3) 0.250000 0.141 (2) 0.053 (6)*
C5 0.53183 (17) 0.29178 (4) −0.12272 (12) 0.0378 (3)
H5A 0.6054 (18) 0.3191 (5) −0.1391 (14) 0.040 (4)*
H5B 0.4308 (18) 0.2929 (4) −0.1844 (13) 0.037 (3)*
C6 0.35549 (16) 0.33369 (4) 0.04520 (12) 0.0368 (3)
C7 0.62831 (17) 0.29169 (5) 0.11125 (13) 0.0407 (3)
H7A 0.697 (2) 0.3186 (5) 0.0955 (15) 0.045 (4)*
H7B 0.5918 (19) 0.2914 (5) 0.2038 (15) 0.046 (4)*
C8 0.28670 (18) 0.40265 (5) 0.15983 (14) 0.0446 (3)
H8 0.312 (2) 0.4236 (5) 0.2279 (17) 0.055 (4)*
C9 0.38864 (18) 0.36491 (4) 0.14268 (12) 0.0409 (3)
H9 0.488 (2) 0.3614 (5) 0.1984 (15) 0.049 (4)*
C10 0.22509 (18) 0.50958 (4) 0.08941 (14) 0.0431 (3)
C11 0.10724 (19) 0.37861 (5) −0.01702 (14) 0.0492 (3)
H11 0.006 (2) 0.3841 (5) −0.0740 (17) 0.059 (5)*
C14 0.3927 (3) 0.57476 (7) 0.1025 (3) 0.0785 (6)
H14A 0.342 (3) 0.5879 (9) 0.025 (3) 0.105 (8)*
H14B 0.494 (4) 0.5609 (10) 0.084 (3) 0.133 (11)*
H14C 0.393 (4) 0.6001 (10) 0.162 (3) 0.122 (9)*
C15 0.6389 (2) 0.250000 −0.14931 (17) 0.0397 (4)
H15 0.677 (3) 0.250000 −0.242 (2) 0.046 (5)*
C16 0.20994 (19) 0.34148 (5) −0.03302 (14) 0.0481 (3)
H16 0.180 (2) 0.3201 (5) −0.1052 (18) 0.060 (5)*
C17 0.7977 (3) 0.250000 −0.05962 (19) 0.0468 (5)
H17 0.872 (2) 0.2772 (5) −0.0764 (15) 0.047 (4)*
C18 0.0881 (2) 0.48334 (5) 0.16032 (15) 0.0459 (3)
H18A 0.1281 (18) 0.4756 (5) 0.2464 (16) 0.043 (4)*
H18B −0.011 (2) 0.5017 (5) 0.1661 (15) 0.053 (4)*

1 Source of material

1,8-Diiodoanthracene (430 mg, 1 mmol) was placed in a 50-ml Schlenk flask along 4,4 -(adamantane-1,3-diyl)diphenol (320 mg, 1 mmol), methyl 2-bromoacetate (334 mg, 2.2 mmol) and Na2CO3 (552 mg, 4.0 mmol) were placed in a 50-ml Schlenk flask along with 30 ml CH3CN. The reaction was stirred in the dark at 60 °C for 2 days. The solvent was removed in vacuo; the residue was dissolved in dichloromethane, washed with water, and then washed with brine. The organic fraction was dried with Na2SO4, filtered through a silica gel plug, and the solvent was removed on a rotary evaporator to produce the title product (441 mg, 0.95 mmol) as a white solid. Crystals were obtained by slow vapor of solution of title compound in CH2Cl2 within 1 week.

2 Experimental details

Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

3 Comment

Adamantane is one of the most stable hydrocarbons [3], [4], [5]. This high degree of stability is due to its arrangement of four cyclohexane rings fused with each in the favorable chair conformation. Moreover, adamantane has a highly symmetrical structure with nearly spherical molecules that can be packed tightly into a lattice and easily crystallized in common organic solvents. Self-assembled adamantanoids were first introduced by Saalfrank and co-workers [6], [7], [8]. Zeng and co-works reported the preparation of polymeric hydrogen-bonded supramolecules by self-assembling of adamantane derivatives with bipyridines [9]. Richert’s group reported that tetrakis(dimethoxyphenyl)adamantane can act as a protective crystalline coat for reagents, enabling the formulation of reactive, malodorous, or toxic compounds [10]. Very recently, we reported the use of 4,4 -(adamantane-1,3-diyl)diphenol as a non-porous adaptive crystal to separate benzene from mixed vapors of cyclohexane and BTX under conditions of room temperature and atmospheric pressure [11]. Herein, as continue work, we reported the synthesis of dimethyl 2,2 -((adamantane-1,3-diylbis(4,1-phenylene))bis(oxy))diacetate. The title compound, built up by the C28H32O6 molecules. In the title crystal structure the molecules are located on a mirror plane. The single-crystal structure verifies that all bond lengths are in normal ranges [12, 13].


Corresponding author: Fei Zeng, Department of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou Hunan 425199, People’s Republic of China, E-mail:

Funding source: National Natural Science Foundation of China

Award Identifier / Grant number: 21602055

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This work was supported by National Natural Science Foundation of China No. 21602055.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Supplementary Material

This article contains supplementary material (https://doi.org/10.1515/ncrs-2023-0188).


Received: 2023-04-19
Accepted: 2023-05-08
Published Online: 2023-05-18
Published in Print: 2023-08-28

© 2023 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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