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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 and Haifeng Zhang
Published/Copyright: December 15, 2021
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 237 Issue 1

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.

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https://doi.org/10.1515/ncrs-2021-0404
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of (E)-7-hydroxy-2-((6-methoxypyridin-3-yl)methylene)-3, 4-dihydronaphthalen-1(2H)-one, C17H15NO3
  4. Crystal structure of (E)-7-methoxy-2-((2-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1 (2H)-one, C18H17NO3
  5. The crystal structure of N 6,N 6′-di(pyridin-2-yl)-[2,2′-bipyridine]-6,6′-diamine, C20H16N6
  6. The crystal structure of {N 1,N 2-bis[2,4-dimethyl-6-(4-(tert-butyl)phenyl)(phenyl)methyl]acenaphthylene-1,2-diimino-κ2 N, N′}-dibromido-nickel(II) – dichloromethane(1/2), C64H64Br2Cl4N2Ni
  7. Synthesis and crystal structure of nonacarbonyltris[(2-thia-1,3,5-triaza-7-phosphatricylco[3.3.1.1]decane-κ1 P)-2,2-dioxide]triruthenium(0) – acetonitrile (7/6), C25.71H32.57N9.86O15P3S3Ru3
  8. A new polymorph of 1-(4-nitrophenyl)-1H-benzimidazole (C13H9N3O2)
  9. The crystal structure of 2,2′-((1E,1′E)-(naphthalene-2,3 diylbis(azanylylidene)) bis(methanylylidene))bis(4-methylphenol), C26H22N2O2
  10. The crystal structure of bis(μ2-iodido)-bis(η6-benzene)-bis(iodido)-diosmium(II), C12H12I4Os2
  11. Redetermination of the crystal structure of bis{hydridotris(3,5-dimethylpyrazol-1-yl-κN 3)borato}copper(II), C30H44B2CuN12
  12. Crystal structure of (E)-3-((4-(tert-butyl)phenyl)thio)-4-hydroxypent-3-en-2-one, C15H20O2S
  13. Crystal structure of 2,2′-(p-tolylazanediyl)bis(1-phenylethan-1-one), C23H21NO2
  14. Redetermination of the crystal structure of the crystal sponge the poly[tetrakis(μ3-2,4,6-tris(pyridin-4-yl)-1,3,5-triazine)-dodecaiodidohexazinc(II) nitrobenzene solvate], C72H48I12N24Zn6⋅10(C6H5NO2)
  15. Crystal structure of (4′E)-6′-(diethylamino)-2-[(E)-[(6-methylpyridin-2-yl)methylidene]amino]-4′-{2-[(2E)-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene]ethylidene}-1′,2,2′,3,3′,4′-hexahydrospiro[isoindole-1,9′-xanthene]-3-one, C44H45N5O2
  16. Crystal structure of (E)-7-fluoro-2-(3-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C17H12F2O1
  17. Crystal structure of tetrabutylammonium sulfanilate – 1-(diaminomethylene)thiourea (1/2)
  18. Crystal structure of [2,2′-{azanediyl)bis[(propane-3,1-diyl)(azanylylidene)methylylidene]} bis(3,5-dichlorophenolato)-κ2O,O′]-isothiocyanato-κN-iron(III), C21H19Cl4FeN4O2S
  19. Crystal structure of (4-chlorophenyl)(4-hydroxyphenyl)methanone, C13H9ClO2
  20. Crystal structure of 6,6′-((pentane-1,3-diylbis(azaneylylidene))bis(methaneylylidene))bis(2,4-dibromolphenolato-κ4 N,N′,O,O′)copper(II),) C19H16Br4CuN2O2
  21. Chlorido-(2,2′-(ethane-bis(5-methoxyphenolato))-κ4 N,N′,O,O′)manganese(III) monohydrate, C19H18Cl2CuN2O2
  22. Crystal structure of 2,6-di-tert-butyl-4-(4-methoxybenzylidene)cyclohexa-2,5-dien-1-one, C22H28O2
  23. Crystal structure of [6,6′-(((2,2-dimethylpropane-1,3-diyl)bis(azanylylidene))bis(methanylylidene))bis(2-chlorophenolato)-κ4N,N′,O,O′]copper(II)
  24. Crystal structure of 2-chloro-3-((thiophen-2-ylmethyl)amino)naphthalene-1,4-dione, C30H20O4N2Cl2S2
  25. Crystal structure of bis{hydridotris(3-trifluoromethyl-5-methylpyrazolyl-1-yl)borato-κN 3}manganese(II), C30H26B2F18MnN12
  26. Crystal structure of 1-(2-methylphenyl)-2-(2-methylbenzo[b]thienyl)-3,3,4,4,5,5-hexafluorocyclopent-ene, C21H14F6S
  27. Crystal structure of 2-(3-((carbamimidoylthio)methyl)benzyl)isothiouronium hexafluorophosphate monohydrate, C10H17F6N4OPS2
  28. Crystal structure of 4,5-diiodo-1,3-dimesityl-1H-1,2,3-triazol-3-ium chloride – chloroform (1/1), C21H23Cl4I2N3
  29. Crystal structure of azido-k1 N-{6,6′-((((methylazanediyl)bis(propane-3,1-diyl))bis(azanylylidene))bis(methanylylidene))bis(2,4-dibromophenolato)k5 N,N′,N″,O,O′}cobalt(III)-methanol (1/1)), C21H23Br4CoN6O3
  30. The crystal structure of 2-(4-((carbamimidoylthio)methyl)benzyl)isothiouronium hexafluorophosphate monohydrate, C10H17F6N4OPS2
  31. Crystal structure of 1,1′-(methane-1,1-diyl)bis(3-methyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C9H14F12N4P2
  32. Crystal structure of (4′E)-6′-(diethylamino)-2-[(E)-[(pyren-1-yl)methylidene]amino]-4′-{2-[(2E)-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene]ethylidene}-1′,2,2′,3,3′,4′-hexahydrospiro[isoindole-1,9′-xanthene]-3-one, C54H48N4O2
  33. Crystal structure of poly[bis(μ2-2,6-bis(1-imidazoly)pyridine-κ2 N,N′)-bis(thiocyanato-κ1 N)copper(II)] dithiocyanate, C24H18CuN12S2
  34. Cones with a three-fold symmetry constructed from three hydrogen bonded theophyllinium cations that coat [FeCl4]− anions in the crystal structure of tris(theophyllinium) bis(tetrachloridoferrate(III)) chloride trihydrate, C21H33Cl9Fe2N12O9
  35. Crystal structure of 14-O-[(4-(4-hydroxypiperidine-1-yl)-6-methylpyrimidine-2-yl)thioacetyl]-mutilin monohydrate, C32H49N3O6S
  36. The crystal structure of (E)-3-chloro-2-(2-(4-methylbenzylidene)hydrazinyl)pyridine, C13H12ClN3
  37. The crystal structure of 4-phenyl-4-[2-(pyridine-4-carbonyl)hydrazinylidene]butanoic acid, C16H15N3O3
  38. The crystal structure of 6-amino-5-carboxypyridin-1-ium pentaiodide monohydrate C6H9I5N2O3
  39. Crystal structure of bis(μ3-oxido)-bis(μ2-2-formylbenzoato-k2O:O′)-bis(2-(dimethoxymethyl)-benzoato-κO)-oktakismethyl-tetratin(IV)
  40. Crystal structure of 2-((E)-(((E)-2-hydroxy-4-methylbenzylidene) hydrazineylidene)methyl)-4-methylphenol, C16H16N2O2
  41. Crystal structure of (E)-amino(2-((5-methylfuran-2-yl)methylene)hydrazinyl) methaniminium nitrate monohydrate, C14H26N10O10
  42. The crystal structure of N′-(2-chloro-6-hydroxybenzylidene)thiophene-2-carbohydrazide monohydrate, C12H11ClN2O3S
  43. Crystal structure of catena-poly[(μ2-1,1′-(biphenyl-4,4′-diyl)bis(1H-imidazol)-κ2N:N′)-bis(4-bromobenzoate-κ1O)zinc(II)], C64H44Br4N8O8Zn2
  44. The crystal structure of catena-poly[(1-(4-carboxybenzyl)pyridin-1-ium-4-carboxylato-κ1O)-(μ2-oxalato-κ4 O:O′:O″:O‴)dioxidouranium(VI)], C16H11NO10U
  45. Crystal structure of 3-allyl-4-(2-bromoethyl)-5-(4-methoxyphenyl)-2-phenylfuran, C22H21BrO2
  46. Halogen bonds in the crystal structure of 4,3′:5′,4″-terpyridine — 1,3-diiodotetrafluorobenzene (1/1), C21H11F4I2N3
  47. Crystal structure of 2-(1H-indol-3-yl)ethan-1-aminium 2-(4-acetylphenoxy)acetate, C20H22N2O4
  48. Chalcogen bonds in the crystal structure of 4,7-dibromo-2,1,3-benzoselenadiazole, C6H2Br2N2Se
  49. The crystal structure of 1,4-bis((1H-benzimidazol-2-yl)methyl)-piperazine-2,5-dione dihydrate, C20H22N6O4
  50. The crystal structure of C19H20O8
  51. The crystal structure of KNa3Te8O18·5H2O exhibiting a ∞2[Te4O9]2− layer
  52. Erratum
  53. Erratum to: Crystal structure of (Z)-3-(6-bromo-1H-indol-3-yl)-1,3-diphenylprop-2-en-1-one, C23H16BrNO
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