Startseite Crystal structure of dichlorido-bis(4-methylphenyl-κC1)tin(IV), C14H14Cl2Sn
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Crystal structure of dichlorido-bis(4-methylphenyl-κC1)tin(IV), C14H14Cl2Sn

  • Kong Mun Lo , See Mun Lee und Edward R. T. Tiekink ORCID logo EMAIL logo
Veröffentlicht/Copyright: 2. August 2021

Abstract

C14H14Cl2Sn, orthorhombic, P212121 (no. 19), a = 8.2912(1) Å, b = 9.6221(1) Å, c = 18.5616(2) Å, V = 1480.82(3) Å3, Z = 4, R gt (F) = 0.0142, wR ref (F2) = 0.0347, T = 100 K.

CCDC no.: 2097904

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 prism
Size: 0.09 × 0.07 × 0.05 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 16.8 mm−1
Diffractometer, scan mode: XtaLAB Synergy, ω
θmax, completeness: 67.0°, >99%
N(hkl)measured, N(hkl)unique, Rint: 38312, 2639, 0.040
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2618
N(param)refined: 157
Programs: CrysAlisPRO [1], SHELX [2, 3], WinGX/ORTEP [4]
Table 2:

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

Atom x y z Uiso*/Ueq
Sn 0.55837 (3) 0.53509 (2) 0.34302 (2) 0.02290 (7)
Cl1 0.56232 (15) 0.33157 (8) 0.41163 (5) 0.03720 (19)
Cl2 0.31081 (10) 0.52845 (10) 0.28244 (4) 0.03371 (18)
C1 0.5463 (5) 0.7073 (3) 0.41350 (16) 0.0220 (6)
C2 0.4743 (4) 0.8302 (3) 0.39066 (17) 0.0240 (7)
H2 0.427956 0.835529 0.343940 0.029*
C3 0.4701 (4) 0.9443 (3) 0.43564 (17) 0.0250 (7)
H3 0.421188 1.028018 0.419476 0.030*
C4 0.5369 (4) 0.9382 (3) 0.50481 (16) 0.0243 (7)
C5 0.6073 (4) 0.8141 (4) 0.52696 (18) 0.0265 (7)
H5 0.652294 0.807884 0.573918 0.032*
C6 0.6131 (4) 0.6999 (3) 0.48201 (18) 0.0239 (7)
H6 0.662612 0.616295 0.497929 0.029*
C7 0.5358 (5) 1.0640 (3) 0.55302 (19) 0.0347 (8)
H7A 0.540008 1.034330 0.603490 0.052*
H7B 0.436823 1.117408 0.544716 0.052*
H7C 0.629677 1.122278 0.542248 0.052*
C8 0.7400 (4) 0.5162 (3) 0.26390 (17) 0.0236 (7)
C9 0.7637 (4) 0.6277 (3) 0.21719 (19) 0.0281 (8)
H9 0.698230 0.708345 0.221031 0.034*
C10 0.8830 (4) 0.6206 (3) 0.1652 (2) 0.0296 (7)
H10 0.897950 0.696945 0.133443 0.036*
C11 0.9816 (4) 0.5042 (3) 0.15818 (18) 0.0265 (7)
C12 0.9548 (5) 0.3925 (3) 0.20462 (17) 0.0275 (7)
H12 1.019064 0.311249 0.200175 0.033*
C13 0.8357 (4) 0.3980 (3) 0.25727 (17) 0.0253 (7)
H13 0.819593 0.321236 0.288646 0.030*
C14 1.1155 (4) 0.5018 (4) 0.10386 (19) 0.0347 (9)
H14A 1.080827 0.550186 0.060062 0.052*
H14B 1.142538 0.405248 0.092130 0.052*
H14C 1.210588 0.548329 0.123880 0.052*

Source of material

The title compound was prepared following a multi-step synthesis. Initially, 4-methylphenylmagnesium bromide was prepared from the Grignard reaction, conducted in tetrahydrofuran, of magnesium (Merck) and 4-bromotoluene (Fluka). Subsequently, tetra(4-methylphenyl)tin was synthesised from the reaction of stannic chloride (Fluka) with 4-methylphenylmagnesium bromide in a 1:4 M ratio. Tetra(4-methylphenyl)tin (10.0 g, 20.7 mmol) and anhydrous stannic chloride (Fluka, 5.39 g, 20.7 mmol) were mixed in a round-bottomed flask fitted with a reflux condenser. The reaction mixture was then heated with stirring in an oil bath at 473–493 K for 3 h. The resulting brown viscous liquid was dissolved in chloroform (150 mL) and boiled with activated charcoal for 10 min. After filtration, the chloroform solution was concentrated to a small volume. Slow evaporation of the concentrated solution gave the product as a white crystalline solid. Yield: 5.35 g (69.5%). M.pt (Stuart SMP30 digital melting point apparatus; uncorrected): 321–322 K (Lit. [5]: 322–323 K). IR (Bruker Vertex 70v FTIR Spectrometer; cm−1): 1560 (m) ν(C═C), 794 (w) ν(C–H), 277 (w) ν(Sn–Cl). 1H NMR (Bruker Ascend 400 MHz NMR spectrometer; CDCl3; ppm relative to Me4Si): δ 2.41 (s, 6H, CH3), 7.29–7.47 (m, 4H, Ph–H), 7.54–7.67 (m, 4H, Ph–H). 13 C{ 1 H} NMR (as for 1H NMR): δ 21.7 (CH3), 130.5, 133.5, 134.9, 142.3 (Ph–C).

Experimental details

The C-bound H atoms were geometrically placed (C–H = 0.95–0.98 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). The crystal was refined as an inversion twin with the minor component = 0.074(7).

Comment

In crystal engineering endeavours, to systematically replace substituents while retaining space group symmetry offers opportunities to tailor chemical and physical properties. This concept is no better illustrated than by the chloro/methyl exchange [6]. As electronegative-chloride and electropositive-methyl groups occupy approximately the same volume, substitution of one by the other in the same crystal symmetry potentially enables control of, for example, electronic properties in the crystalline manifold. In continuation of on-going studies of opportunities offered by the chloro/methyl exchange [7, 8], herein, the crystal and molecular structures of (4–MeC6H4)2SnCl2, hereafter (I) and a known compound [5], was studied and compared with the recently reported crystal structure of the chloro analogue (4–ClC6H4)2SnCl2 [9].

The molecular structure of (I), which lacks crystallographic symmetry, is shown in the figure (70% displacement ellipsoids). The donor set defining an approximate tetrahedral geometry for the tin atom is C2Cl2, with the range of angles subtended at the tin atom being 104.55(4)°, for Cl1–Sn–Cl2, to 122.12(13)° for C1–Sn–C8, in accord with expectation as the rings have a greater steric profile. The Sn–Cl bond lengths are experimentally distinct [Sn–Cl1 = 2.3362(8) Å and Sn–Cl2 = 2.3413(8) Å], whereas the Sn–C distances are equivalent [Sn–C1 = 2.112(3) Å and Sn–C7 = 2.114(3) Å]. The observed molecular geometry for (I) and patterns in bond lengths match very closely that noted for (4–ClC6H4)2SnCl2 [9].

In accord with the distance criteria in PLATON [10], the only directional intermolecular contact in the crystal of (I) is a weak methyl–C–H⃛π(4-tolyl) contact [C14–H14b⃛Cg(C1–C6) i : H14b⃛Cg(C1–C6) i  = 2.90 Å, C14⃛Cg(C1–C6) i  = 3.527(4) Å with the angle at H14b = 123° for symmetry operation (i) 2 − x, −1/2 + y, 1/2 − z] occurring within helical chains along the b-axis. This description of the molecular packing differs significantly from the observed molecular packing in (4–ClC6H4)2SnCl2, which is not isostructural with (I). Prominent in the crystal of (4–ClC6H4)2SnCl2 were Sn⃛Cl secondary-bonding as well as C–Cl⃛π(phenyl) contacts [9].

To gain a further appreciation of the molecular packing, a detailed analysis of all surface contacts in the crystal of (I) was conducted by the calculation, using Crystal Explorer 17 [11], of the Hirshfeld surfaces and two-dimensional fingerprint plots (full and delineated into individual contacts), following established protocols [12]. The analysis revealed the dominance of three types of surface contacts, namely H⃛H [38.4%], Cl⃛H/H⃛Cl [3.7%] and C⃛H/H⃛C [28.2%] with the next most significant contacts being Cl⃛C/C⃛Cl at 1.6%.


Corresponding author: Edward R. T. Tiekink, Research Centre for Crystalline Materials, School of Medical and Life Sciences, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia, E-mail:

Funding source: Sunway University

Award Identifier / Grant number: GRTIN–IRG-01–2021

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

  2. Research funding: Crystallographic research at Sunway University is supported by Sunway University Sdn Bhd (Grant No. GRTIN–IRG-01–2021).

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

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Received: 2021-07-12
Accepted: 2021-07-20
Published Online: 2021-08-02
Published in Print: 2021-12-20

© 2021 Kong Mun Lo et al., published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. Redetermination of the crystal structure of 3-bromonitrobenzene at 200 K, C6H4BrNO2 – temperature effects on cell constants
  4. Crystal structure of (E)-ethyl 2-((4-oxo-4H-chromen-3-yl)methyleneaminooxy)acetate, C14H13NO5
  5. Crystal structure of (8R,10R,14R, Z)-2-((3–Fluoropyridin-4-yl) methylene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6, 6-trimethyltetrahydro-2H-pyran-2-yl) hexadecahydro-3H-cyclopenta[a] phenanthren-3-one, C36H52FNO3
  6. Crystal structure of [6,6′-((1E,1′E)-(propane-1,3- diylbis(azaneylylidene))bis(methaneylylidene)) bis(3-chlorophenol)-κ4N,N′,O,O′] copper(II), C17H14Cl2CuN2O2
  7. The crystal structure of 6-amino-2-carboxypyridin-1-ium bromide, C6H7BrN2O2
  8. Redetermination of the crystal structure of bis[N,N′-ethylenebis(acetylacetoniminato)nickel(II)] sodium perchlorate, C24H36ClN4NaNi2O8
  9. The crystal structure of 3-methyl-2,6-dinitrophenol, C7H6N2O5
  10. The crystal structure of 5-chloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H9ClN2O2
  11. Crystal structure of trans-tetraaqua-bis{2-carboxy-4-((5-carboxypyridin-3-yl)oxy)benzoato-κ1 N}cobalt(II) dihydrate C28H28O20N2Co
  12. Crystal structure of 3-allyl-4-(2-bromoethyl)-5-(4-methoxyphenyl)-2-(p-tolyl)furan, C23H23BrO2
  13. The crystal structure of 6,6′-(((2-(dimethylamino)ethyl)azanediyl)bis(methylene))bis(benzo[d][1,3]dioxol-5-ol ato-κ4N,N′,O,O′)-(pyridine-2,6-dicarboxylato-N,O,O′)-titanium(IV)-dichloromethane(1/1), C27H25N3O10Ti
  14. Crystal structure of (((1E,1′E)-1,2-phenylenebis(methaneylylidene))bis(hydrazin-1-yl-2-ylidene))bis(aminomethaniminium) dinitrate C10H16N10O6
  15. Crystal structure of catena-poly[triaqua-(μ 2-1,3-di(1H-imidazol-1-yl)propane-κ 2 N:N′)-(4,4′-(1H-1,2,4-triazole-3,5-diyl)dibenzoato-κ 1 O)nickel(II)]N,N′-dimethylformamide (1/1), C28H35N8O8Ni
  16. The crystal structure of 3,3′-[1,4-phenylenebis(methylene)]bis(1-ethenyl-1H-imidazol-3-ium) dichloride – dichloromethane – water (1/1/1), C19H24Cl4N4O1
  17. Crystal structure of 1,1′-(methane-1,1-diyl)bis(3-propyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C13H22F12N4P2
  18. Crystal structure of dichlorido-bis(4-chlorophenyl-κC 1)tin(IV), C12H8Cl4Sn
  19. Synthesis and crystal structure of 4-acetylpyrene, C18H12O
  20. Crystal structure of 2,2′-(butane-1,4-diylbis(azanylylidene))bis(methanylylidene))bis(4-methoxyphenol), C20H24N2O4
  21. The crystal structure of (E)-2-(((5-((triphenylstannyl)thio)-1,3,4-thiadiazol-2-yl)imino)methyl)phenol, C27H21N3OS2Sn
  22. Crystal structure of diaqua-bis(μ2-6-phenylpyridine-2-carboxylate-κ3N,O:O)-bis(6-phenylpyridine-2-carboxylato-κ2N,O)lead(II) – N,N-dimethylformamide – water (1/2/4), C54H58N6O16Pb2
  23. Crystal structure of methyl 4-acetoxy-3-methoxybenzoate, C11H12O5
  24. Crystal structure of 2,2′-(propane-1,3-dilylbis(azaneylylidene))bis(methanylylidene)bis(4-methylphenol), C19H22N2O2
  25. Crystal structure of dichlorido-bis(4-methylphenyl-κC1)tin(IV), C14H14Cl2Sn
  26. Crystal structure of methyl (E)-3-(4-acetoxyphenyl)acrylate, C12H12O4
  27. The crystal structure of bis(benzoato-κ2 O,O′)-(2,9-dimethyl-1,10-phenanthroline-κ2 N,N′)-copper(II), C28H22CuN2O4
  28. Crystal structure of (8R,10R,14R,Z)-12-hydroxy-2-((6-methoxypyridin-2-yl)methylene)-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-3H-cyclopenta[a]phenanthren-3-one–water (2/1), C37H56NO4.5
  29. Crystal structure of dimethyl-bis(4-bromophenyl-κC1)tin(IV), C14H14Br2Sn
  30. The crystal structure of the cocrystal di-μ2-chlorido-octamethyl-di-μ3-oxido-bis(2,3,4,5-tetrafluorobenzoato-κ2 O,O′)tetratin(IV) ─ octamethyl-di-μ3-oxido-bis(μ2-2,3,4,5-tetrafluorobenzoato-κ2 O:O′)-bis(μ2-2,3,4,5-tetrafluorobenzoato-κ2 O:O;O′)tetratin(IV) C58H54Cl2F24O16Sn8
  31. Crystal structure of 3-iodo-N 2-(2-methyl-1-(methylsulfonyl)propan-2-yl)-N 1-(2-methyl-4-(perfluoropropan-2-yl)phenyl)phthalamide, C23H22F7I1N2O4S1
  32. Crystal structure of 1-(2-(4-bromophenyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)-naphthalen-2-ol – dichloromethane – dimethyl sulfoxide (1/1/1), C28H18BrNO·CH2Cl2·C2H6SO
  33. Crystal structure of [meso-5,7,7,12,14,14,-hexamethyl-1,4,8,11-tetraazacyclotetradecane]nickel(II) diperchlorate – dimethylsulphoxide (1/2), C20H48Cl2N4NiO10S2
  34. Crystal structure of 1,1′-(1,3-phenylenebis(methylene))bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S) palladium(II), C26H18N6PdS4
  35. The crystal structure of bis(6-phenylpyridine-2-carboxylato-κ2 N,O)copper(II), C24H16N2O4Cu
  36. Crystal structure of dichlorido-bis(4-chlorophenyl-κC)-bis(triphenylarsine oxide-κO)tin(IV), C48H38As2Cl4O2Sn
  37. Crystal structure of (4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane-κ 8 N 2, O 6) potassium cyclopentadienide, [K([2.2.2]crypt)]Cp, C23H41KN2O6
  38. The crystal structure of bis(2-oxidopyridin-1-ium-3-carboxylato-κ2O,O′)-(phenantroline-κ2N,N′)manganese(II) - methanol (1/3), C27H28N4O9Mn
  39. Crystal structure of 4-(dimethylamino)pyridinium dibromido-tris(4-chlorophenyl-κC)stannate(IV), C25H23Br2Cl3N2Sn
  40. Crystal structure of (3E,5E)-1-(4-cyanobenzenesulfonyl)-3,5-bis(3-fluorobenzylidene)piperidin-4-one-dichloromethane (1/1), C27H20Cl2F2N2O3S
  41. Crystal structure of (3E,5E)-3,5-bis(4-fluorobenzylidene)-1-((4-trifluoromethyl)benzenesulfonyl)piperidin-4-one, C26H18F5NO3S
  42. Crystal structure of chlorido-(4-methyl-2-((phenylimino)methyl)phenolato-κ2 N,O)-(pyridine-κ1 N)platinum(II), C19H17ClN2OPt
  43. Crystal structure of (4-methylbenzyl)(triphenyl)phosphonium chloride dihydrate, C26H28ClO2P
  44. The crystal structure of poly[μ2-chlorido-(μ2-1,2-bis(4-pyridyl)ethane-κ2N:N′silver(I)], C12H12AgClN2
  45. Crystal structure of poly[(μ4-benzene-1,2,4,5-tetracarboxylato)-bis(μ2-adipohydrazide)dicadmium], C11H15N4O6Cd
  46. The crystal structure of (E)-N′-(butan-2-ylidene)isonicotinohydrazide 0.5 hydrate C10H13N3O·0.5H2O
  47. The crystal structure of bis(6-phenylpyridine-2-carboxylate-κ2 N,O)-(2,2′-bipyridine-κ2 N,N′)zinc(II) monohydrate, C34H26N4O5Zn
  48. The crystal structure of (1R *,2S *)-1,2-bis(2-fluorophenyl)-3,8-dimethoxyacenaphthene-1,2-diol, C26H20F2O4
  49. Crystal structure of catena-poly[(μ2-1-((2-ethyl-4-methyl-1H-imidazol-1-yl)methyl)-1H-benzotriazole-κ2N:N′)-(nitrato-κ2O,O′)silver (I)], C13H15Ag1N6O3
  50. The crystal structure of [(phenantroline-κ2 N,N′)-bis(6-phenylpyridine-2-carboxylate-κ2 N,O)cobalt(II)]monohydrate, C36H26N4O5Co
  51. Crystal structure of (1E)-N-[(1E)-1-(4-chlorophenyl)ethylidene]-2-[1-(4-chlorophenyl)ethylidene]hydrazine-1-carbohydrazonamide, C 17 H 17 Cl 2 N 5
  52. The crystal structure of (E)-2-((tert-butylimino)methyl)-4-chlorophenol, C11H14ClNO
  53. Crystal structure of all-cis-2,4,6-trihydroxycyclohexane- 1,3,5-triaminium chloride sulfate, C6H18ClN3O7S
  54. Crystal structure of dichlorido-bis(dimethyl sulfoxide-κO)bis(4-methylphenyl-κC 1)tin(IV), C18H26Cl2O2S2Sn
  55. Crystal structure of dichlorido-bis(4-chlorophenyl-κC 1)(2,2′-bipyridyl-κ 2 N,N′)tin(IV), C22H16Cl4N2Sn
  56. Redetermination of the crystal structure of (E)-5-bromo-2-hydroxybenzaldehyde oxime, C 7 H 6 BrNO 2
  57. The crystal structure of (E)-amino(2-(4-methylbenzylidene)hydrazineyl)methaniminium 4-methylbenzoate, C9H13N4 + C8H7O2
  58. Crystal structure of 2-chloro-3-(isopentylamino)naphthalene-1,4-dione, C 15 H 16 ClNO 2
  59. The crystal structure of bis(2-acetyl-5-methoxyphenyl)carbonate 1.5 hydrate, C19H18O7
  60. The crystal structure of poly[(μ 4-4,4′-(azanediylbis(methylene))dibenzoato-κ 4 O:N:O′:Oʺ)zinc(II)], C16H13NO4Zn
  61. The crystal structure of catena-poly[(1,10-phenanthroline-k2N,N′)-(μ3-tetraoxidomoybdato(VI)-k3O:O′:O″)manganese(II)] C12H8N2O4MoMn
  62. Crystal structure of catena-poly[(4-hydroxyl-5-(methoylcarbonyl)thiophene-2-carboxylato-κ1 O)-(μ2-piperazine-1,4-diylbis(pyridin-4-ylmethanone)-κ2 N:N′)silver(I)] monohydrate, C23H23AgN4O8S
  63. Crystal structure of bis(4-bromo-2-(((3-bromopropyl)imino)methyl)phenolato-κ2N,O)-oxido-vanadium(IV), C20H20Br4N2O3V
  64. The crystal structure of (2a′S,2a1′S,3R,5a′S,7′R)-5-(furan-3-yl)-2a′,2a1′-dihydroxy-7′-methyldecahydro-2H-spiro[furan-3,6′-naphtho[1,8-bc]furan]-2,2′(2a′H)-dione, C19H22O7
  65. The crystal structure of 3-bromopicolinic acid, C6H4BrNO2
  66. Crystal structure of 1,1′-(1,4-phenylenebis(methylene))bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S,S) platinum(II), C26H18N6PtS4
  67. Synthesis and crystal structure of 5-(8-((3-carboxyazetidin-1-ium-1-yl)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxybenzenesulfonate monohydrate, C20H19NO10S
  68. The crystal structure of 3-amino-5-carboxypyridin-1-ium bromide, C6H7BrN2O2
  69. The crystal structure of (2-hydroxy-5-methyl-phenyl)-(1H-pyrazol-4-yl)-methanone hemihydrate, C11H10.5N2O2.5
  70. Crystal structure of tetraaqua-(2-(4-formylphenoxy)acetato-k1O)cadmium(II), C18H22O12Cd
  71. Crystal structure of diethyl 6,12-dimethyl-3,9-di-p-tolyl-3,9-diazapentacyclo[6.4.0.02,7.04,11.05,10]dodecane-1,5-dicarboxylate, C32H38N2O4
  72. Crystal structure of (E)-N′-(1-(3-chloro-4-fluorophenyl)ethylidene)-4-hydroxy – tetrahydrofuran (2/1), C17H16ClFN2O2.5
Heruntergeladen am 16.11.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2021-0281/html
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