Startseite Crystal structure of bis(μ3-oxido)-bis(μ2-2-formylbenzoato-k2O:O′)-bis(2-(dimethoxymethyl)-benzoato-κO)-oktakismethyl-tetratin(IV)
Artikel Open Access

Crystal structure of bis(μ3-oxido)-bis(μ2-2-formylbenzoato-k2O:O′)-bis(2-(dimethoxymethyl)-benzoato-κO)-oktakismethyl-tetratin(IV)

  • Zhongjun Gao ORCID logo EMAIL logo und Haifeng Zhang
Veröffentlicht/Copyright: 15. Dezember 2021

Abstract

C44H56O16Sn4, triclinic, P 1 (no. 2), a = 9.129(7) Å, b = 11.826(9) Å, c = 13.612(17) Å, α = 109.954(17)°, β = 98.165(16)°, γ = 102.862(12)°, V = 1308(2) Å3, Z = 1, R gt (F) = 0.0298, wR ref (F2) = 0.0806, T = 298 K.

CCDC no.: 2100743

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: Colorless block
Size: 0.24 × 0.19 × 0.16 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 1.95 mm−1
Diffractometer, scan mode: D8, φ and ω
θmax, completeness: 25.0°, 99%
N(hkl)measured, N(hkl)unique, Rint: 6793, 4589, 0.014
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 3838
N(param)refined: 289
Programs: Bruker [1], SHELX [2], Olex2 [3]
Table 2:

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

Atom x y z Uiso*/Ueq
Sn1 0.88529 (3) 0.99072 (3) 0.08214 (2) 0.04000 (10)
Sn2 1.02440 (3) 0.71698 (3) −0.02104 (2) 0.04359 (10)
O1 0.7318 (4) 1.1180 (3) 0.1449 (3) 0.0596 (9)
O2 0.4614 (7) 1.0493 (6) 0.3182 (6) 0.153 (3)
O3 1.0250 (3) 0.8935 (2) −0.0090 (2) 0.0445 (7)
O4 1.1201 (4) 0.6936 (3) −0.1694 (3) 0.0592 (8)
O5 0.9153 (4) 0.7750 (3) 0.1128 (3) 0.0557 (8)
O6 0.9044 (5) 0.5892 (3) 0.1209 (3) 0.0688 (10)
O7 1.1505 (6) 0.7337 (5) 0.3326 (4) 0.1097 (16)
O8 1.0526 (6) 0.6514 (5) 0.4526 (3) 0.1003 (15)
C1 0.7644 (5) 1.2369 (4) 0.1825 (3) 0.0456 (10)
C2 0.6610 (5) 1.2969 (4) 0.2451 (3) 0.0456 (10)
C3 0.5661 (6) 1.2380 (5) 0.2963 (4) 0.0540 (11)
C4 0.4659 (6) 1.2981 (6) 0.3476 (4) 0.0693 (15)
H4 0.401489 1.259245 0.381119 0.083*
C5 0.4623 (7) 1.4131 (6) 0.3486 (5) 0.0794 (17)
H5 0.396484 1.452812 0.383786 0.095*
C6 0.5555 (7) 1.4710 (5) 0.2978 (5) 0.0768 (17)
H6 0.551642 1.549126 0.298325 0.092*
C7 0.6547 (6) 1.4130 (4) 0.2461 (4) 0.0593 (12)
H7 0.717433 1.452261 0.211958 0.071*
C8 0.5670 (8) 1.1150 (6) 0.3028 (5) 0.0834 (18)
H8 0.654522 1.088256 0.294344 0.100*
C9 1.0244 (6) 1.0656 (5) 0.2391 (4) 0.0641 (13)
H9A 0.987123 1.014532 0.277187 0.096*
H9B 1.129223 1.066887 0.236336 0.096*
H9C 1.020546 1.149765 0.275716 0.096*
C10 0.6696 (5) 0.8668 (5) −0.0155 (4) 0.0612 (13)
H10A 0.627384 0.812472 0.018575 0.092*
H10B 0.600237 0.914324 −0.025556 0.092*
H10C 0.682926 0.817178 −0.084157 0.092*
C11 1.2415 (6) 0.7310 (5) 0.0670 (4) 0.0682 (14)
H11A 1.245097 0.649069 0.062990 0.102*
H11B 1.321519 0.764997 0.037368 0.102*
H11C 1.256893 0.785379 0.140843 0.102*
C12 0.8248 (6) 0.5784 (4) −0.1294 (4) 0.0615 (13)
H12A 0.829607 0.497026 −0.132359 0.092*
H12B 0.734681 0.594394 −0.105439 0.092*
H12C 0.819057 0.580522 −0.199640 0.092*
C13 0.8867 (6) 0.6939 (5) 0.1574 (4) 0.0527 (11)
C14 0.8254 (6) 0.7387 (5) 0.2570 (4) 0.0597 (13)
C15 0.8896 (7) 0.7269 (5) 0.3524 (4) 0.0684 (15)
C16 0.8312 (9) 0.7708 (6) 0.4419 (5) 0.093 (2)
H16 0.872501 0.764265 0.505623 0.111*
C17 0.7123 (11) 0.8240 (6) 0.4369 (6) 0.116 (3)
H17 0.675838 0.854764 0.498197 0.139*
C18 0.6452 (11) 0.8329 (7) 0.3427 (7) 0.121 (3)
H18 0.563175 0.867185 0.339926 0.145*
C19 0.7035 (8) 0.7894 (6) 0.2531 (6) 0.089 (2)
H19 0.659804 0.794378 0.189308 0.107*
C20 1.0212 (7) 0.6663 (6) 0.3545 (5) 0.0772 (16)
H20 0.984075 0.582057 0.297044 0.093*
C21 1.2145 (11) 0.8570 (8) 0.4048 (7) 0.141 (4)
H21A 1.302022 0.896188 0.384097 0.212*
H21B 1.138703 0.901724 0.404872 0.212*
H21C 1.247148 0.858580 0.475634 0.212*
C22 1.1492 (11) 0.5672 (9) 0.4492 (7) 0.137 (3)
H22A 1.168624 0.558921 0.517217 0.205*
H22B 1.096623 0.486113 0.393378 0.205*
H22C 1.245553 0.601399 0.434744 0.205*

Source of material

A mixture of dimethyltin oxide (0.3296 g, 2.0 mmol) and 2-formylbenzoic acid (0.300 g, 2.0 mmol), in methanol (50 ml) was heated under reflux for 7 h. The clear solution was evaporated under vacuum. The product was crystallized from a mixture of dichloromethane/methanol (1:1) to yield block crystals of the title compound. Yield 0.467 g, 71%, m.p. 431 K. Analysis, calculated for C22H28O8Sn2: C 40.17, H, 2.99%; found: C 40.22, H 3.03%.

Experimentaldetails

H atoms were included in the riding model approximation with C–H 0.93–0.96 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Comment

In recent years, the di-carboxylato-tetraalkyl distannoxanes have been studied thoroughly and uniform views are formed that the majority has a tetranuclear centrosymmetric structure with a planar four-membered Sn2O2 ring [4], [5], [6], [7]. In parallel, we were interested in finding out whether formyl groups coordinate intramolecularly to tin.

The title structure is a cluster build by inversion symmetry around the central Sn2O2 ring. Both unique SnO3C2 centers have distorted trigonal bipyramidal geometry. 2-formylbenzoic acid reacts with methanol to form 2-(dimethoxymethyl)benzoic acid. The formyl groups are not coordinate intramolecularly to any tin (IV) atom. For Sn1, C9, C10 and O3 i [symmetry operation i: 2−x, 2−y, −z] occupied the equatorial positiona and O1, O3 are in axial positions. The sum of the bond angles of C9–Sn1–C10, O3i–Sn1–C9 and O3i–Sn1–C10 are 358.4°, which demonstrated that O3i, Sn1, C9 and C10 are almost in the same plane. The bond angle of O1–Sn1–O3 is 164.5°, showing the distortion. For Sn2, O3, C11 and C12 occupied the equatorial positions and O4, O5 are in axial positions. The bond angle of O5–Sn2–O4 is 166.2(12)°. The bond angle of C11–Sn2–C12 is 139.6(2)°, O3-Sn2–C11 is 107.33(18)° and O3–Sn–C12 is 112.46(17)°, the sum of them is 359.39°, indicating coplanarity for these atoms. The bond lengths of Sn1–O1 is 2.315(3) Å, Sn1–O3 is 2.149(3) Å, Sn2–O5 is 2.179(3) Å and Sn2–O4 is 2.269(4) Å, which is close to reported measures [8], [9], [10], [11].


Corresponding author: Zhongjun Gao, School of Chemistry, Chemical Engineering and Materials, Jining University, Qufu, 273155, Shandong Province, China, E-mail:

Funding source: National Research Foundation http://dx.doi.org/10.13039/501100001321

Funding source: Talent Team Plan for Leading disciplines of University in Shandong Province

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

  2. Research funding: This study was financially supported by National Research Foundation (2217011475) and the Talent Team Plan for Leading disciplines of University in Shandong Province.

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

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Received: 2021-10-19
Accepted: 2021-12-02
Published Online: 2021-12-15
Published in Print: 2022-02-23

© 2021 Zhongjun Gao and Haifeng Zhang, published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

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