Home Crystal structure of catena-poly[tetrakis(butyl)-μ2-2-((oxido(phenyl)methylene)hydrazineylidene)propanoato-κ4 O:O,O′,N-μ2-2-((oxido(phenyl)methylene)hydrazineylidene)propanoato-κ4 O,N,O′:N′-ditin(IV)], C34H50N6O6Sn2
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Crystal structure of catena-poly[tetrakis(butyl)-μ2-2-((oxido(phenyl)methylene)hydrazineylidene)propanoato-κ4 O:O,O′,N-μ2-2-((oxido(phenyl)methylene)hydrazineylidene)propanoato-κ4 O,N,O′:N′-ditin(IV)], C34H50N6O6Sn2

  • Zhongjun Gao ORCID logo EMAIL logo and Haifeng Zhang
Published/Copyright: May 15, 2023

Abstract

C34H50N6O6Sn2, triclinic, P 1 , a = 12.110(2) Å, b = 12.406(2) Å, c = 13.744(3) Å, α =  79.547 ( 2 ) ° , β =  82.072 ( 2 ) ° , γ =  87.257 ( 2 ) ° , V = 2010.7(7) Å3, Z = 2, R gt (F) = 0.0471, wR ref (F 2) = 0.1392, T = 298 K.

CCDC no.: 2248036

The asymmetric unit of the title crystal 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: 0.30 × 0.20 × 0.10 mm
Wavelength: Mo radiation (0.71073 Å)
μ: 1.29 mm−1
Diffractometer, scan mode: φ and ω
θ max, completeness: 25.0°, 98 %
N(hkl)measured , N(hkl)unique, R int: 10,055, 6951, 0.022
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 5574
N(param)refined: 439
Programs: Bruker [1], SHELX [2], Olex2 [3]
Table 2:

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

Atom x Y z U iso*/U eq
Sn1 0.29540 (3) 0.11744 (3) 0.18751 (3) 0.04148 (14)
Sn2 0.26282 (3) 0.44821 (3) 0.25646 (3) 0.04228 (14)
O1 0.2271 (4) 0.5870 (3) 0.3297 (3) 0.0568 (12)
O2 0.2117 (5) 0.1128 (3) 0.4189 (4) 0.0656 (13)
O3 0.2600 (4) 0.2549 (3) 0.2984 (3) 0.0482 (10)
O4 0.3340 (4) 0.2779 (3) 0.1026 (3) 0.0509 (11)
O5 0.3960 (5) 0.3734 (3) −0.0453 (4) 0.0689 (14)
O6 0.2960 (4) −0.0657 (3) 0.1673 (3) 0.0530 (11)
N1 0.0557 (7) 0.7378 (5) 0.6083 (5) 0.089 (2)
N2 0.3044 (5) −0.3857 (4) 0.1177 (4) 0.0516 (13)
N3 0.1661 (5) 0.4705 (4) 0.4762 (4) 0.0493 (13)
N4 0.1989 (4) 0.3922 (4) 0.4181 (4) 0.0455 (12)
N5 0.3467 (4) −0.0022 (4) −0.0009 (4) 0.0443 (12)
N6 0.3457 (4) 0.0982 (4) 0.0292 (4) 0.0423 (11)
C1 0.0861 (7) 0.8376 (6) 0.5609 (6) 0.0794 (19)
H1 0.065043 0.896823 0.592808 0.095*
C2 0.1465 (7) 0.8580 (6) 0.4680 (6) 0.0756 (18)
H2 0.165236 0.929078 0.437398 0.091*
C3 0.1788 (6) 0.7705 (5) 0.4210 (6) 0.0695 (17)
H3 0.218221 0.781959 0.357097 0.083*
C4 0.1524 (6) 0.6666 (5) 0.4688 (5) 0.0555 (14)
C5 0.0908 (6) 0.6555 (6) 0.5614 (6) 0.0671 (16)
H5 0.072216 0.584928 0.593719 0.080*
C6 0.1842 (6) 0.5686 (5) 0.4211 (5) 0.0521 (14)
C7 0.1488 (7) 0.2503 (6) 0.5654 (5) 0.070 (2)
H7A 0.193598 0.279672 0.606374 0.106*
H7B 0.153936 0.171626 0.579306 0.106*
H7C 0.072549 0.273737 0.579669 0.106*
C8 0.1892 (5) 0.2896 (5) 0.4597 (5) 0.0483 (14)
C9 0.2222 (5) 0.2111 (5) 0.3882 (5) 0.0497 (14)
C10 0.1154 (6) 0.4407 (6) 0.1920 (6) 0.0626 (17)
H10A 0.135727 0.426690 0.124585 0.075*
H10B 0.072654 0.379105 0.229745 0.075*
C11 0.0419 (7) 0.5431 (8) 0.1882 (8) 0.090 (2)
H11A 0.025121 0.560089 0.254944 0.108*
H11B 0.082469 0.604006 0.146505 0.108*
C12 −0.0654 (9) 0.5318 (10) 0.1482 (9) 0.115 (3)
H12A −0.049520 0.508070 0.084150 0.138*
H12B −0.110274 0.476558 0.193602 0.138*
C13 −0.1287 (12) 0.6380 (13) 0.1363 (12) 0.169 (5)
H13A −0.132751 0.667944 0.196414 0.253*
H13B −0.202764 0.626311 0.123396 0.253*
H13C −0.091612 0.688191 0.081481 0.253*
C14 0.1196 (6) 0.1127 (7) 0.2013 (6) 0.0674 (16)
H14A 0.095077 0.050395 0.252011 0.081*
H14B 0.088888 0.178314 0.225016 0.081*
C15 0.0730 (8) 0.1051 (10) 0.1114 (8) 0.100 (2)
H15A 0.106308 0.041350 0.085918 0.120*
H15B 0.094567 0.169151 0.061669 0.120*
C16 −0.0553 (9) 0.0963 (11) 0.1228 (10) 0.120 (3)
H16A −0.088981 0.154984 0.155715 0.144*
H16B −0.078431 0.107351 0.056792 0.144*
C17 −0.0973 (12) −0.0063 (13) 0.1782 (11) 0.159 (4)
H17A −0.036868 −0.050993 0.202996 0.239*
H17B −0.132127 −0.043449 0.135361 0.239*
H17C −0.151094 0.006987 0.233166 0.239*
C18 0.4460 (6) 0.0776 (6) 0.2496 (6) 0.0665 (17)
H18A 0.503081 0.062897 0.196551 0.080*
H18B 0.468085 0.141900 0.272465 0.080*
C19 0.4456 (8) −0.0154 (9) 0.3325 (7) 0.097 (2)
H19A 0.420544 −0.079566 0.311442 0.117*
H19B 0.392133 0.000521 0.387744 0.117*
C20 0.5599 (9) −0.0426 (10) 0.3698 (8) 0.109 (3)
H20A 0.578791 0.012189 0.406496 0.130*
H20B 0.618072 −0.046037 0.314216 0.130*
C21 0.5449 (13) −0.1632 (13) 0.4430 (12) 0.180 (5)
H21A 0.496835 −0.155524 0.503119 0.270*
H21B 0.616455 −0.191709 0.459325 0.270*
H21C 0.512669 −0.212735 0.409209 0.270*
C22 0.4376 (7) 0.4339 (10) 0.2513 (9) 0.103 (3)
H22A 0.461850 0.362441 0.235996 0.124*
H22B 0.471322 0.488831 0.197352 0.124*
C23 0.4761 (10) 0.4461 (15) 0.3389 (13) 0.169 (4)
H23A 0.434471 0.397477 0.393523 0.203*
H23B 0.458399 0.520512 0.349512 0.203*
C24 0.6050 (12) 0.4231 (15) 0.3461 (14) 0.170 (4)
H24A 0.617310 0.378218 0.409437 0.204*
H24B 0.640985 0.388180 0.291972 0.204*
C25 0.6407 (12) 0.5263 (17) 0.3382 (15) 0.212 (6)
H25A 0.593666 0.576675 0.299861 0.318*
H25B 0.716078 0.531228 0.305560 0.318*
H25C 0.637547 0.544299 0.403603 0.318*
C26 0.3682 (5) 0.2887 (4) 0.0082 (5) 0.0466 (14)
C27 0.3723 (5) 0.1844 (4) −0.0347 (4) 0.0428 (12)
C28 0.4048 (6) 0.1871 (5) −0.1431 (5) 0.0574 (16)
H28A 0.456243 0.127495 −0.153022 0.086*
H28B 0.439643 0.255334 −0.172565 0.086*
H28C 0.339671 0.180124 −0.173954 0.086*
C29 0.3190 (5) −0.0799 (5) 0.0780 (5) 0.0466 (12)
C30 0.3185 (5) −0.1923 (5) 0.0540 (5) 0.0456 (12)
C31 0.3328 (6) −0.2126 (5) −0.0413 (5) 0.0563 (14)
H31 0.342047 −0.155207 −0.095364 0.068*
C32 0.3333 (7) −0.3204 (5) −0.0563 (5) 0.0637 (15)
H32 0.342249 −0.336027 −0.120593 0.076*
C33 0.3206 (6) −0.4032 (5) 0.0244 (5) 0.0617 (16)
H33 0.323489 −0.475173 0.013474 0.074*
C34 0.3040 (5) −0.2819 (5) 0.1311 (5) 0.0495 (13)
H34 0.293343 −0.268583 0.196277 0.059*

1 Source of material

A mixture of dibutyltin oxide (0.4979 g, 2.0 mmol) and pyruvic acid nicotinyl hydrazone (0.4144 g, 2.0 mmol), in methanol (30 mL) was heated under reflux for 5 h. The obtained clear solution was evaporated under vacuum. The product was crystallized from a mixture of dichloromethane/ethanol (1:1). Yield 0.6659 g, 76 %, m.p. 467 K.

2 Experimental details

H atoms were included in the riding model approximation with C–H 0.93–0.97 Å, and with U iso (H) = 1.2U eq (C) or 1.5U eq (methyl C).

3 Comment

The studies of organotin(IV) compounds are of current interest owing to their wide range of applications as biocides and homogeneous catalysts in industry. Recently organotin(IV) compounds with Schiff bases have attracted considerable attention owing to their biological activity and diverting structure [4], [5], [6], [7], [8]. We are exploring whether or not the hetero-atoms (N, O or S) of the carboxylic acid are to influence the coordination mode and extension of diaryltin(IV) compounds with heteroatom carboxylate ligands. We have synthesized and structurally characterized a new dibutyltin(IV) compound with pyruvic acid nicotinyl hydrazone.

In this compound, every tin atom is six-coordination in a distorted tetragonal bipyramidal geometry and center tin atom is surrounded equatorially by four O or N atoms from the nicotinyl hydrazone ligand, and axis position were occupied by two C atoms from the trans butyl groups (see the figure). It is quit clear that the identical hydrazone ligands coordinate in a different way (see name in the title and figure) [9].

The whole structure consists of molecular units connected by intermolecular Sn–N interactions and formed a one-dimensional chain structure. The bond length of Sn2–N2A 2.558(5) Å, Sn1–N6 2.229(4) Å and Sn2–N4 2.245(5) Å, which is greater than the sum of the covalent radii of Sn and N (2.15 Å), but is considerably less than the sum of the van der Waals radii (3.75 Å), and should be considered as bonding interactions [10].


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

  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 Natural Science Foundation of China (grant no. 2217011475).

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

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Received: 2023-03-15
Accepted: 2023-05-01
Published Online: 2023-05-15
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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  55. The crystal structure of catena-poly[5-aminonicotinic acid-k1 N-m2-bromido-copper(I)], Cu(C6N2H6O2)Br
  56. The crystal structure of 2,2-bis(3-methoxyphenyl)-1-tosyl-1,2-dihydro- 4,3λ4  -[1,3,2]diazaborolo[4,5,1-ij]quinoline - dichloromethane (1/1)
  57. The crystal structure of catena-poly[bis(6-phenylpyridine-2-carboxylato-κ2 N,O)-(μ2-4,4′-bipyridne-κ2 N:N)cadmium(II)], C34H24N4O4Cd
  58. The crystal structure of 5,7-dinitropyrazolo[5,1-b]quinazolin-9(4H)-one, C10H5N5O5
  59. Crystal structure of rac-1,8-bis(2-carbamoylethyl)-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane, C22H46N6O2
  60. The crystal structure of (E)-N -(2-bromobenzylidene)-2-naphthohydrazide, C36H26Br2N4O2
  61. The crystal structure of 5-nitronaphthoquinone, C10H5NO4
  62. The crystal structure of (S, R p )-4–benzhydrylideneamino-12-(4-tert-butyl oxazolin-2-yl)[2.2]paracyclophane, C36H36N2O
  63. Synthesis and crystal structure of 2-(2-oxo-2-(o-tolyl)ethyl)-4H-chromen-4-one, C18H14O3
  64. Crystal structure of 2-(thiazol-2-yl)hexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione, C11H10N2O3S
  65. Crystal structure of N-(diaminomethylene)-1-(dimethylamino)-1-iminiomethanaminium dichloride, C4H13Cl2N5
  66. Crystal structure of poly[(μ3-3, 5-dichloro-2-hydroxy-benzoato-κ4 Cl,O:O′:O″) silver(I)], C7H3AgCl2O3
  67. The crystal structure of tetrakis(1-isopropylimidazole-κ1 N)-[μ2- imidazole-4,5-dicarboxylato-κ4 O,N,O′,N′)]- trioxido-divanadium, C29H41N10O7V2
  68. Crystal structure of catena-[(μ3-bromido)-(1H-1,2,4-triazol-1-yl)benzoato-κ1 N)copper(I)], C9H7BrCuN3O2
  69. The crystal structure of (E)-4-fluoro-N′-(1-(2-hydroxyphenyl)propylidene)benzohydrazide, C16H15FN2O2
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