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Crystal structure of dichlorido-bis(4-chlorophenyl-κC 1)tin(IV), C12H8Cl4Sn

  • Kong Mun Lo , See Mun Lee and Edward R. T. Tiekink ORCID logo EMAIL logo
Published/Copyright: August 2, 2021
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 236 Issue 6

Abstract

C12H8Cl4Sn, monoclinic, P21/c (no. 14), a = 13.4238(1) Å, b = 18.2079(2) Å, c = 5.7617(1) Å, β = 95.506(1)°, V = 1401.77(3) Å3, Z = 4, R gt (F) = 0.0272, wR ref (F 2) = 0.0798, T = 100 K.

CCDC no.: 2097861

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: 0.26 × 0.06 × 0.04 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 21.3 mm−1
Diffractometer, scan mode: XtaLAB Synergy, ω
θ max, completeness: 67.1°, >99%
N(hkl)measured, N(hkl)unique, R int: 17318, 2491, 0.042
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 2456
N(param)refined: 154
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 U iso*/U eq
Sn 0.69707 (2) 0.38500 (2) 0.14457 (3) 0.01743 (11)
Cl1 0.71380 (5) 0.30683 (3) −0.17040 (10) 0.02162 (16)
Cl2 0.68098 (5) 0.50129 (3) −0.02919 (11) 0.02462 (17)
Cl3 1.08960 (6) 0.37999 (4) 0.92412 (15) 0.0347 (2)
Cl4 0.23910 (5) 0.34664 (4) 0.45676 (14) 0.03184 (19)
C1 0.8316 (3) 0.38803 (14) 0.3654 (5) 0.0209 (6)
C2 0.8474 (2) 0.44579 (16) 0.5220 (5) 0.0253 (6)
H2 0.802879 0.486491 0.512635 0.030*
C3 0.9282 (2) 0.44429 (17) 0.6928 (5) 0.0288 (6)
H3 0.939041 0.483496 0.801085 0.035*
C4 0.9923 (2) 0.38482 (15) 0.7019 (6) 0.0234 (7)
C5 0.9801 (2) 0.32818 (16) 0.5405 (5) 0.0232 (6)
H5 1.026672 0.288785 0.544848 0.028*
C6 0.8990 (2) 0.33008 (15) 0.3729 (5) 0.0211 (5)
H6 0.889385 0.291425 0.262309 0.025*
C7 0.5536 (2) 0.36617 (15) 0.2538 (5) 0.0190 (5)
C8 0.4833 (2) 0.32459 (15) 0.1188 (5) 0.0210 (6)
H8 0.501629 0.300018 −0.016197 0.025*
C9 0.3858 (2) 0.31884 (15) 0.1809 (5) 0.0232 (6)
H9 0.337130 0.291553 0.086473 0.028*
C10 0.3607 (2) 0.35287 (15) 0.3795 (5) 0.0238 (6)
C11 0.4306 (3) 0.39390 (16) 0.5203 (6) 0.0235 (6)
H11 0.412298 0.416897 0.658026 0.028*
C12 0.5269 (2) 0.40051 (17) 0.4558 (5) 0.0217 (6)
H12 0.575122 0.428522 0.549389 0.026*

Source of material

The title compound was prepared from a multi-step synthesis. Initially, 4-chlorophenylmagnesium bromide was prepared from the Grignard reaction of magnesium (Merck) and 4-bromochlorobenzene (Fluka) [in tetrahydrofuran]. Tetra(4-chlorophenyl)tin was synthesised from the reaction of stannic chloride (Fluka) with 4-chlorophenylmagnesium bromide in a 1:4 M ratio. Tetra(4-chlorophenyl)tin (5 g, 10.3 mmol) and anhydrous stannic chloride (Fluka, 2.7 g, 10.3 mmol) were mixed together in a round-bottomed flask fitted with a reflux condenser. The reaction mixture was then heated with stirring by 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 and the filtrate was evaporated slowly until a colourless crystalline compound was formed. Yield: 3.02 g (67.0%). M.pt (Stuart SMP30 digital melting point apparatus; uncorrected): 354–356 K (lit.: 361 K [5]). IR (Bruker Vertex 70v FTIR Spectrometer; cm−1): 1562 (m) ν(C═C), 723 (w) ν(C–H), 723 (w) ν(C–Cl), 270 (w) ν(Sn–Cl). 1 H NMR (Bruker Ascend 400 MHz NMR spectrometer; CDCl3; ppm relative to Me4Si): δ 7.50–7.55 (m, 4H, Ph–H), 7.60–7.66 (m, 4H, Ph–H). 13 C{ 1 H} NMR (as for 1H NMR): δ 130.0, 134.7, 136.2, 138.9 (Ph–C).

Experimental details

The atoms were geometrically placed (C–H = 0.95 Å) and refined as riding with U iso(H) = 1.2U eq(C). Owing to poor agreement, three reflections, i.e. (1 0 0), (2 0 0) and (1 1 0), were omitted from the final cycles of refinement.

Comment

The crystal structure determination of the title compound (4-ClC6H4)2SnCl2, hereafter (I), a known compound [5], was studied in continuation of long-term interests in the structural chemistry of diorganotin dihalides, i.e. R2SnX2, and their adducts with chelating bipyridine-type molecules, i.e. R2SnX2(NN) [6], [7], [8]. Recently, the structures of (4-ClC6H4)2SnCl2(NN) for NN = 1,10-phenanthroline [9] and (4-ClC6H4CH2)2SnCl2(NN) for NN = 2,2′-bipyridine [10] became available. The present report of the structure determination of (I) now enables a comparison of the geometric parameters about the tin atoms in these systems and the influence of the chloro-substituted rings upon molecular packing.

The molecular structure of (I) is shown in the upper view of the figure (70% displacement ellipsoids); the molecule lacks crystallographic symmetry. The tin atom in (I) exists within a distorted tetrahedral geometry defined by a C2Cl2 donor set. The minimum and maximum angles subtended at the tin atom, i.e. 102.99(8)° for Cl2–Sn–C7, and 125.29(11)° for C1–Sn–C7, are consistent with the increased steric pressure induced by the 4-chlorophenyl substituents. While the Sn–Cl bond lengths are experimentally distinct [Sn–Cl1 = 2.3341(6) Å and Sn–Cl2 = 2.3432(6) Å], the Sn–C distances are equivalent [Sn–C1 = 2.108(4) Å and Sn–C7 = 2.111(3) Å].

As mentioned in the Introduction, there are closely related structures available for comparison [8], [9], [10]. The most closely related structure is that of (4-ClC6H4)2SnCl2(1,10-phenanthroline), hereafter (II) [9]. Here, the tin atom is found within a C2Cl2N2 donor set with a cis disposition of the chlorido atoms which form experimentally equivalent Sn–Cl bond lengths [Sn–Cl = 2.4934(4) and 2.4960(4) Å] which are significantly longer than those found in (I), reflecting the increased coordination number in (II).

As shown in the lower view of the figure (H atoms are removed for clarity), the most notable feature in the crystal of (I) are zig-zag supramolecular chains along the c-axis (glide-symmetry) where molecules are connected by Sn⃛Cl⃛Sn secondary-bonding interactions [Sn⃛Cl1 i  = 3.6525(7) Å for symmetry operation (i): x, 1/2−y, 1/2+z; shown as dashed lines in the image]. Such secondary-bonding interactions are well-documented in the structural chemistry of diorganotin dihalides [11]; DFT calculations proved these Sn⃛X interactions exerted a significant influence upon the molecular geometry about the tin atoms [11]. The only other directional bonding interactions apparent in the molecular packing are end-on Sn–Cl⃛π(phenyl) contacts [Sn–Cl2⃛Cg(C7–C12) ii : Cl2⃛Cg(C7–C12) i i  = 3.4685(13) Å, with angle at Cl2 = 152.70(3)° for symmetry operation (ii) 1−x, 1−y, −z]. The latter contacts link the aforementioned chains into double chains. The connections between the double chains within a three-dimensional architecture are of the type Cl⃛Cl halogen bonding but at separations greater than the sum of their van der Waals radii, i.e. 3.50 Å [12]. The closest halogen bonding contact is noted for Cl1⃛Cl1 iii [3.5471(8) Å for (iii) x, 1/2−y, −1/2+z].

A further analysis of the molecular packing was achieved by the calculation of Hirshfeld surfaces and two-dimensional fingerprint plots (full and delineated into individual contacts). This was accomplished employing the Crystal Explorer 17 program [13] following established protocols [14]. The identified Sn⃛Cl [1.0%] and Cl⃛π [13.0%] contacts in the molecular packing make relatively minor contributions to the overall Hirshfeld surface. Significant contributions are made by Cl⃛H/H⃛Cl [41.1%], C⃛H/H⃛C [18.9%], H⃛H [16.0%] and Cl⃛Cl [8.9%] contacts but at separations greater than the sum of the respective van der Waals radii.

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 doi.org/10.13039/501100010798

Award Identifier / Grant number: STR-RCTR-RCCM-001-2019.

  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 financially supported by Sunway University Sdn Bhd Grant No. STR-RCTR-RCCM-001-2019.

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

References

1. Rigaku Oxford Diffraction. CrysAlisPro; Rigaku Corporation: Oxford, UK, 2018.Search in Google Scholar

2. Sheldrick, G. M. A short history of SHELX. Acta Crystallogr. 2008, A64, 112–122; https://doi.org/10.1107/s0108767307043930.Search in Google Scholar PubMed

3. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Search in Google Scholar

4. Farrugia, L. J. WinGX and ORTEP for Windows: an update. J. Appl. Crystallogr. 2012, 45, 849–854; https://doi.org/10.1107/s0021889812029111.Search in Google Scholar

5. Ingham, R. K., Rosenberg, S. D., Gilman, H. Organotin compounds. Chem. Rev. 1960, 60, 459–539; https://doi.org/10.1021/cr60207a002.Search in Google Scholar

6. Buntine, M. A., Hall, V. J., Kosovel, F. J., Tiekink, E. R. T. Influence of crystal packing on molecular geometry: a crystallographic and theoretical investigation of selected diorganotin systems. J. Phys. Chem. 1998, 102, 2472–2482; https://doi.org/10.1021/jp9728722.Search in Google Scholar

7. Buntine, M. A., Hall, V. J., Tiekink, E. R. T. The crystal and molecular structures of R2SnCl2(1,10-phenanthroline), R = iPr, Cy, CH2Ph and R2 = Me, Ph: a comparison between solid state and theoretical structures. Z. Kristallogr. - Cryst. Mater. 1998, 213, 669–678; https://doi.org/10.1524/zkri.1998.213.12.669.Search in Google Scholar

8. Kumar Das, V. G., Keong, Y. C., Wei, C., Smith, P. J., Mak, T. C. W. The first authenticated example of geometrical isomers in organotin(IV) co-ordination chemistry. the crystal and molecular structures of octahedral cis- and trans-SnR2 isomeric adducts of dichlorobis(4-chlorophenyl)tin(IV) with 4,4'-dimethyl-2,2'-bipyridyl. J. Chem. Soc., Dalton Trans. 1987, 129–137; https://doi.org/10.1039/dt9870000129.Search in Google Scholar

9. Lo, K. M., Lee, S. M., Tiekink, E. R. T. Crystal structure of dichloridobis(4-chlorophenyl-κC1)(1,10-phenanthroline-κ2N,N′)tin(IV), C24H16Cl4N2Sn. Z. Kristallogr. NCS 2019, 234, 695–697.10.1515/ncrs-2019-0903Search in Google Scholar

10. Lee, S. M., Lo, K. M., Tiekink, E. R. T. Crystal structure of (2,2′-bipyridyl)bis(4-chlorobenzyl)dichloridotin(IV), C24H20Cl4N2Sn. Z. Kristallogr. NCS 2019, 234, 1321–1323; https://doi.org/10.1515/ncrs-2019-0508.Search in Google Scholar

11. Buntine, M. A., Kosovel, F. J., Tiekink, E. R. T. Supramolecular Sn…Cl associations in diorganotin dichlorides and their influence on molecular geometry as studied by ab initio molecular orbital calculations. CrystEngComm 2003, 5, 331–336; https://doi.org/10.1039/b308922c.Search in Google Scholar

12. Spek, A. L. checkCIF validation ALERTS: what they mean and how to respond. Acta Crystallogr. 2020, E76, 1–11; https://doi.org/10.1107/s2056989019016244.Search in Google Scholar

13. Turner, M. J., Mckinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D., Spackman, M. A. Crystal Explorer (v17); The University of Western Australia: Australia, 2017.Search in Google Scholar

14. Tan, S. L., Jotani, M. M., Tiekink, E. R. T. Utilizing Hirshfeld surface calculations, non-covalent interaction (NCI) plots and the calculation of interaction energies in the analysis of molecular packing. Acta Crystallogr. 2019, E75, 308–318; https://doi.org/10.1107/s2056989019001129.Search in Google Scholar
Received: 2021-07-06
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.

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  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
https://doi.org/10.1515/ncrs-2021-0271
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Articles in the same Issue

  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
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