Home Physical Sciences Crystal structure of catena-poly[tri(4-chlorophenyl)-(μ2-hydroxido)tin(IV)] – 2-propanol (1/1), C21H21Cl3O2Sn
Article Open Access

Crystal structure of catena-poly[tri(4-chlorophenyl)-(μ2-hydroxido)tin(IV)] – 2-propanol (1/1), C21H21Cl3O2Sn

  • Kong Mun Lo , See Mun Lee and Edward R.T. Tiekink ORCID logo EMAIL logo
Published/Copyright: September 18, 2019
Download Article (PDF)
Become an author with De Gruyter Brill
Submit Manuscript Author Information
Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 235 Issue 1

Abstract

C21H21Cl3O2Sn, monoclinic, P21/n (no. 14), a = 13.3360(1) Å, b = 8.2332(1) Å, c = 20.2443(2) Å, β = 104.070(1)°, V = 2156.10(4) Å3, Z = 4, Rgt(F) = 0.0199, wRref(F2) = 0.0544, T = 100(2) K.

CCDC no.: 1951436

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:0.16 × 0.07 × 0.03 mm
Wavelength:Cu Kα radiation (1.54178 Å)
μ:13.0 mm−1
Diffractometer, scan mode:XtaLAB Synergy, ω
θmax, completeness:67.1°, >99%
N(hkl)measured, N(hkl)unique, Rint:49159, 3845, 0.036
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3647
N(param)refined:252
Programs:CrysAlisPRO [1], SHELX [2], [3], WinGX/ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
Sn0.74641(2)0.62820(2)0.25099(2)0.01366(6)
Cl10.85701(4)0.45614(6)0.58296(2)0.02580(11)
Cl21.14436(5)0.86190(7)0.12846(4)0.04162(15)
Cl30.29619(4)0.47006(6)0.03131(2)0.03108(12)
O10.70141(10)0.87677(13)0.26734(7)0.0165(3)
H1O0.6489(13)0.881(3)0.2829(12)0.025*
C10.78181(13)0.5769(2)0.35770(9)0.0165(3)
C20.72610(15)0.6470(2)0.40081(10)0.0202(4)
H20.67200.72140.38260.024*
C30.74872(16)0.6094(2)0.46977(10)0.0222(4)
H30.71010.65680.49850.027*
C40.82802(14)0.5023(2)0.49600(9)0.0201(4)
C50.88599(14)0.4329(2)0.45525(9)0.0201(4)
H50.94100.36060.47410.024*
C60.86223(13)0.4710(2)0.38622(9)0.0181(4)
H60.90170.42370.35790.022*
C70.87130(13)0.7107(2)0.21065(9)0.0158(3)
C80.96992(14)0.7304(2)0.25384(9)0.0217(4)
H80.97970.71150.30130.026*
C91.05356(15)0.7768(2)0.22895(10)0.0270(4)
H91.12000.78970.25880.032*
C101.03870(16)0.8041(2)0.15984(11)0.0268(4)
C110.94273(16)0.7860(2)0.11552(10)0.0279(4)
H110.93370.80560.06820.033*
C120.85949(14)0.7388(2)0.14113(9)0.0217(4)
H120.79340.72550.11080.026*
C130.60105(13)0.5794(2)0.18139(9)0.0171(3)
C140.50882(15)0.6493(2)0.18890(10)0.0206(4)
H140.51030.72140.22580.025*
C150.41476(16)0.6150(2)0.14327(11)0.0232(4)
H150.35240.66190.14910.028*
C160.41373(14)0.5117(2)0.08945(9)0.0222(4)
C170.50345(15)0.4420(2)0.08004(9)0.0222(4)
H170.50150.37140.04260.027*
C180.59676(14)0.4767(2)0.12617(9)0.0196(4)
H180.65870.42940.11980.024*
O20.52056(12)0.88333(16)0.32963(9)0.0302(3)
H2O0.507(2)0.9835(14)0.3316(14)0.045*
C190.44785(16)0.7908(3)0.35541(11)0.0300(4)
H190.46200.67330.34900.036*
C200.4606(2)0.8188(5)0.43005(13)0.0641(9)
H20A0.53180.79360.45440.096*
H20B0.41290.74840.44670.096*
H20C0.44550.93260.43790.096*
C210.33907(19)0.8250(4)0.31621(14)0.0518(7)
H21A0.32170.93830.32340.078*
H21B0.29140.75270.33200.078*
H21C0.33310.80650.26760.078*

Source of material

All chemicals and solvents were used as purchased without purification. The melting point was determined using a Mel-temp II digital melting point apparatus and was uncorrected. The IR spectrum was obtained on a Perkin-Elmer RX1 spectrophotometer in a Nujol mull between KBr plates from 4000 to 400 cm−1.

Tetra(4-chlorophenyl)tin was prepared from the reaction of stannic chloride (Fluka) and 4-chlorophenylmagnesium bromide (Fluka) in a 1:4 molar ratio. Tetra(4-chlorophenyl)tin (3.40 g, 6 mmol) was dissolved in dimethylformamide (30 mL) and cooled to 273 K in an ice-salt bath. A chilled dimethylformamide solution (5 mL) of bromine (0.97 g, 6 mmol) was added drop-wise into the solution. When the addition was complete, the mixture was stirred at room temperature for 3 h and a 10% sodium hydroxide solution was added drop-wise until a white precipitate was formed. The solid was filtered and recrystallised from 2-propanol to afford the title compound as colourless crystals. Yield: 0.30 g (10%). M.pt: 431–433 K. IR (cm−1) 1568 (m) ν(C—C), 1090 (s) ν(C—O), 1010 (s) ν(C—O), 481 (w) ν(Sn—O).

Experimental details

The C-bound H atoms were geometrically placed (C—H = 0.95–1.00 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). The O-bound H-atoms were located in a difference Fourier map but were refined with a distance restraint of O—H = 0.84 ± 0.01 Å, and with Uiso(H) set to 1.5Ueq(O).

Comment

Molecules of the general formula R3SnOH can be mononuclear as exemplified by R = 2,4,6-Me3C6H2 (mesityl) [5], binuclear, as in the case when R = CF2CF3 [6], or polymeric such as when R = Et [7]. While to a first approximation, the adoption of one structural motif over another for R3SnOH may be attributed to steric effects, well established in organotin chemistry to moderate secondary bonding interactions [8], [9], [10], [11], the subtle nature of the adoption of one motif over another is nicely illustrated in the case when R = Ph. Thus, the structure of Ph3SnOH was established long ago as being polymeric [12] but, when this is co-crystallised with 2,6-bis(1H-benzimidazol-2-yl)pyridine and water [13], it is mononuclear. Herein, the crystal and molecular structures of the R = 4-ClPh derivative, isolated as a 1:1 isopropanol solvate, that is (4-ClPh)3Sn(OH)⋅iPrOH, (I), are described.

The crystallographic asymmetric unit of (I) is shown in the upper part of the figure (70% probability displacement ellipsoids). From symmetry, and as indicated in the lower view of the figure (only ipso-C atoms of the 4-ClPh substituents are shown and the solvent molecules are omitted), the solid-state structure of (I) is a one-dimensional coordination polymer with helical symmetry, being propagated along the b-axis by 21-screw symmetry. The tin atom is therefore coordinated by two hydroxy-O atoms and three ipso-C atoms of the organic substiuents. While, the Sn—C bond lengths are experimentally equivalent, that is, [2.1363(17) Å, for Sn—C7, to 2.1393(17) Å, for Sn—C13], there is a disparity in the Sn—O1 bond lengths with the formally covalent Sn—O1 bond length of 2.1805(11) Å being significantly shorter than the formally intermolecular Sn—O1i bond length of 2.2434(11) Å; symmetry operation (i): 3/2 − x, −1/2 + y, 1/2 − z. As the O1 atoms are approximately trans to each other, the O1—Sn—O1i bond angle is 177.51(2)°, the resultant C3O2 coordination geometry is close to trigonal-bipyramidal.

As indicated in the upper view of the figure, the connection between the constituents of the asymmetric unit is a tin-hydroxy-O—H⋯O(2-propanol) hydrogen bond [O1—H1o⋯O2: H1o⋯O2 = 2.148(19) Å, O1⋯O2 = 2.981(2) Å with angle at H1o = 176(2)°]. The acidic proton of the solvent iPrOH molecule is engaged in an intra-chain 2-propanol-O—H⋯π(phenyl) interaction [O2—H2o⋯π(C7—C12)ii: H2o⋯Cg(C7—C12)ii = 2.353(13) Å, O2⋯Cg(C7—C12)ii = 3.1203(15) Å with angle at H2o = 151(2)° for symmetry operation (ii): 3/2 − x, 1/2 + y, 1/2 − z]. Chains pack in the crystal with no directional interactions between them.

To analyse the molecular packing further, using Crystal Explorer 17 [14] and established protocols [15], Hirshfeld surface calculations were performed along with the full and delineated two-dimensional fingerprint plots. This analysis reveals the importance of Cl⋯H/H⋯Cl (32.2%), H⋯H (30.2%) and C⋯H/H⋯C (25.6%) contacts to the calculated Hirshfeld surface but, these occur at distances generally greater than the sum of the respective van der Waals radii. The next most important contacts are of the type C⋯C, contributing 3.8%.

As indicated above, there are several polymeric precedents for the one-dimensional coordination polymer found in (I). Zig-zag chains are found in the R = Et derivative [7] and in the mixed species, Ph2(Cy)SnOH [16], each of which sees the chain having mirror symmetry. Helical chains propagated by 21 scew axes are found when R = Ph [12], R = CH2Ph [17] and in the mixed species Me2(PhCH2)SnOH [18]. The discussion of these structures would be incomplete without mentioning the structural analyses of the R = Me derivative, which has attracted considerable attention [19]. Since the original room temperature analysis where a helical chain was shown [20], in a subsequent study, {Me3Sn(OH)}n was modelled as a 32-fold superstructure with 83-helical chains [21]. At 220 K, the structure has been described as an eight-fold superstructure, with distorted zig-zag chains [22].

Funding source: Sunway University Sdn Bhd is thanked for financial support

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

Funding statement: Sunway University Sdn Bhd is thanked for financial support of this work through Grant no. STR-RCTR-RCCM-001-2019.

References

1. Agilent Technologies: CrysAlisPRO. Agilent Technologies, Santa Clara, CA, USA (2017).Search in Google Scholar

2. Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar

3. Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Search in Google Scholar

4. Farrugia, L. J.: WinGX and ORTEP for Windows: an update. J. Appl. Crystallogr. 45 (2012) 849–854.10.1107/S0021889812029111Search in Google Scholar

5. Reuter, H.; Puff, H.: Trimesitylzinn-hydroxid und -fluorid als modellsubstanzen zur Bestimmung der normal-Kovalenzabstände Zinn-Sauerstoff und Zinn-Fluor. J. Organomet. Chem. 379 (1989) 223–234.10.1016/0022-328X(89)85162-9Search in Google Scholar

6. Wiesemann, M.; Hoge, B.: Pentafluoroethylated compounds of silicon, germanium and tin. Chem. Eur. J. 24 (2018) 16457–16471.10.1002/chem.201801292Search in Google Scholar PubMed

7. Deacon, G. B.; Lawrenz, E.; Nelson, K. T.; Tiekink, E. R. T.: Crystal structure of polymeric triethyltin hydroxide. Main Group Met. Chem. 16 (1993) 265–269.Search in Google Scholar

8. Tiekink, E. R. T.: Structural chemistry of organotin carboxylates: a review of the crystallographic literature. Appl. Organomet. Chem. 5 (1991) 1–23.10.1002/aoc.590050102Search in Google Scholar

9. 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 5 (2003) 331–336.10.1039/B308922CSearch in Google Scholar

10. Tiekink, E. R. T.: Tin dithiocarbamates: applications and structures. Appl. Organomet. Chem. 22 (2008) 533–550.10.1002/aoc.1441Search in Google Scholar

11. Tiekink, E. R. T.: Supramolecular assembly based on “emerging” intermolecular interactions of particular interest to coordination chemists. Coord. Chem. Rev. 345 (2017) 209–228.10.1016/j.ccr.2017.01.009Search in Google Scholar

12. Glidewell, C.; Liles, D. C.: The crystal and molecular structures of hydroxotriphenyltin(IV) and hydroxotriphenyllead(IV). Acta Crystallogr. B34 (1978) 129–134.10.1107/S0567740878002447Search in Google Scholar

13. Lo, K. M.; Das, V. G. K.; Ng, S. W.: Hydroxotriphenyltin 2,6-bis(1H-benzimidazol-2-yl)pyridine hydrate. Acta Crystallogr. C55 (1999) 1234–1236.10.1107/S0108270199004072Search in Google Scholar

14. 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

15. 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. E75 (2019) 308–318.10.1107/S2056989019001129Search in Google Scholar

16. Lo, K. M.; Ng, S. W.: catena-Poly[[cyclohexyldiphenyltin(IV)]-μ-hydroxido-κ2O:O]. Acta Crystallogr. E64 (2008) m724–m725.10.1107/S1600536808011100Search in Google Scholar

17. Reuter, H.: Crystal structure of tribenzyltin(IV) hydroxide, (C7H7)3SnOH. Z. Kristallogr. NCS 219 (2004) 487–488.10.1524/ncrs.2004.219.14.519Search in Google Scholar

18. Wannagat, U.; Damrath, V.; Huch, V.; Veith, M.; Harder, U.: Sila-Riechstoffe und Riechstoffisostere XII. Geruchsvergleiche homologer organoelementverbindungen der vierten Hauptgruppe (C, Si, Ge, Sn). J. Organomet. Chem. 443 (1993) 153–165.10.1016/0022-328X(93)80293-KSearch in Google Scholar

19. Dey, S.; Schonleber, A.; Mondal, S.; van Smaalen, S.: Superspace description of trimethyltin hydroxide at T = 100 K. Z. Kristallogr. – Cryst. Mater. 231 (2016) 427–434.10.1515/zkri-2016-1952Search in Google Scholar

20. Kasai, N.; Yasuda, K.; Okawara, R.: The crystal structure of trimethyltin hydroxide. J. Organomet. Chem. 3 (1965) 172–173.10.1016/S0022-328X(00)84752-XSearch in Google Scholar

21. Anderson, K. M.; Tallentire, S. E.; Probert, M. R.; Goeta, A. E.; Mendis, B. G.; Steed, J. W.: Trimethyltin hydroxide: a crystallographic and high Z′ curiosity. Cryst. Growth Des. 11 (2011) 820–826.10.1021/cg101464jSearch in Google Scholar

22. Dey, S.; Schonleber, A.; Mondal, S.; Ali, S. I.; van Smaalen, S.: Role of steric hindrance in the crystal packing of Z′ = 4 superstructure of trimethyltin hydroxide. Cryst. Growth Des. 18 (2018) 1394–1400.10.1021/acs.cgd.7b01295Search in Google Scholar

Received: 2019-08-16
Accepted: 2019-09-04
Published Online: 2019-09-18
Published in Print: 2019-12-18

©2019 Kong Mun Lo et al., published by De Gruyter, Berlin/Boston

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

Articles in the same Issue

  1. 10.1515/ncrs-2020-frontmatter1
  2. The crystal structure of 3,5-dicarboxybenzenaminium perchlorate monohydrate, C8H8ClNO9
  3. The crystal structure of poly[(m4-4-bromoisophthalato-κ4O: O′:O′′:O′′′)zinc(II)], C8H3BrO4Zn
  4. Crystal structure of (E)-2-(2-chloro-6-hydroxybenzylidene)hydrazine-1-carbothioamide, C8H8ClN3O4S
  5. Crystal structure of 1,1′-methylenebis(3-ethyl-1H-imidazol-3-ium) bis(hexafluorophosphate(V)), C11H18F12N4P2
  6. The crystal structure of hexakis(1-isopropyl-1H-imidazole-κ1N)copper(II) dichloride, C36H58Cl2CuN12
  7. Crystal structure of catena-poly[μ2-4,4′-bipyridine-κ2N:N′)-tetrakis(μ2-2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-κ2O:O′)dicobalt(II)], C19H10Cl6CoN3O6
  8. Crystal structure of (E)-1-(4-(((E)-2-bromo-6-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H15BrN2O2
  9. Crystal structure of ethyl 2-methyl-4-(5-methylthiophen-2-yl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C18H21NO3S
  10. The crystal structure of 5-bromo-2-(1-methyl-1H-tetrazol-5-yl)pyridine, C7H6BrN5
  11. Crystal structure of Bis(acetato-κ2O,O′)-bis[4-(dimethylamino)pyridine-κN]nickel(II), C18H26N4NiO4
  12. Crystal structure of (E)-3-chloro-2-(((4-chlorophenyl)imino)methyl)phenol, C13H9Cl2NO
  13. The co-crystal structure of (17b)-estra-1,3,5(10)-triene-3,17diol – acetamide (1/1), a Z′ = 4 structure, C20H29NO3
  14. Crystal structure of 3-(3-(pyridin-3-yl)ureido)benzoic acid, C13H11N3O3
  15. The crystal structure of 1,1′-(9-ethyl-9H-carbazole-3,6-diyl)bis(3-ethyl-1H-imidazol-3-ium) bis(hexafluorophosphate(IV)), C24H27N5F12P2
  16. The crystal structure of 2-bromoisophthalic acid, C8H5BrO4
  17. The crystal structure of 13-ethoxycarbonyl-9-methyl-4-chlor-11-thioxo-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2,4,6-triene, C14H15ClN2O3S
  18. The crystal structure of (E)-4-((4-(diethylamino)benzylidene)amino)-N,N-diphenylaniline, C29H29N3
  19. Crystal structure of 2-(3-(2-(4-phenylpiperazin-1-yl)ethyl)benzyl)isoindoline-1,3-dione, C27H27N3O2
  20. Crystal structure of 2-ethoxy-6-((E)-((3-(((E)-3-ethoxy-2-hydroxybenzylidene)amino)-2-hydroxypropyl)iminio)methyl)phenolate, C21H26N2O5
  21. The crystal structure of catena-poly(μ2-4,4′-bipyridine-κ2N:N′)-tetrakis(μ2-2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-κ2O:O′)dinickel(II)], C19H10Cl6N3NiO6
  22. Crystal structure of hexakis(μ2-azido-κ2N:N)-diazido-κ1N-tetrakis(phenanthroline-κ2N,N′)tetrazinc(II), C48H32N32Zn4
  23. Synthesis and crystal structure of bis{2-bromo-6-(((4-(1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O}cobalt(II)–dichloromethane(1/1), C34H32Br2Cl4CoN4O4
  24. Crystal structure of (E)-3-chloro-2-(((4-nitrophenyl)imino)methyl)phenol, C13H9ClN2O3
  25. Crystal structure of aqua-bis(5-bromo-6-methyl-picolinato-κ2N,O)zinc(II) dihydrate, C14H16Br2N2O7Zn
  26. Crystal structure of biaqua(2,2′-bipyridine-4,4′-dicarboxylato-κ2N,N′)(pyridine-2,6-dicarboxylato-κ3O,N,O′)nickel(II) hydrate, C19H15N3NiO10
  27. Synthesis and crystal structure of bis(2-(((4-(1-(ethoxyimino)ethyl)phenyl)imino)methyl)-5-fluorophenolato-κ2N,O)zinc(II) - methanol (1/1), C33H32F2N4O4Zn
  28. Crystal structure of tetraaqua-bis(μ2-5-aminoisophthalato-κ3N:O,O′)-bis(4,4′-dipyridylsulfide-κ1N)dizinc(II), C36H34N6O12S2Ni2
  29. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)palladium(II) tetracyanonickelate(II), C14H24N8NiPd
  30. The crystal structure of 3-benzyl-1-((8-(benzyloxy)quinolin-2-yl)methyl)-1H-imidazol-3-ium hexafluorophosphate, C27H24N3OF6P
  31. Crystal structure of 1-(4-chloro-2-hydroxy-5-iodophenyl)ethan-1-one, C8H6ClIO2
  32. Crystal structure of hexaaquamagnesium(II) bis((E)-4-((4-(dimethylamino)phenyl)diazenyl)benzenesulfonate), C28H40MgN6O12S2
  33. Crystal structure of the coordination polymer catena-poly[(1,2-di(pyridin-4-yl)ethane-κN)-(μ2-2-nitroisophthalato-κ2O:O′)zinc(II)], C20H17N3O7Zn
  34. Crystal structure of catena-{[tri-aqua-di-sodium bis(2-{[n-butyl(methyl)carbamothioyl]sulfanyl}acetate)]}n, [C16H34N2Na2O7S4]n
  35. The crystal structure of diaqua-bis(μ2-3-((3-acetyl-5-carboxyphenyl)oxidophosphoryl)-5-carboxybenzoato-κ2O:O′)bis(5,5′-dimethyl-2,2′-bipyridine-k2N,N′)zinc(II), C56H46N4O22P2Zn2
  36. Crystal structure of N′,2-bis((E)-2-chloro-6-hydroxybenzylidene)hydrazine-1-carbothiohydrazide, C15H12Cl2N4O2S
  37. Crystal structure of 2-[(1E)-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]iminiumyl}methyl]-5-(dodecyloxy)benzen-1-olate, C23H39NO5
  38. Crystal structure of 12-(2-hydroxybenzoyl)benzo[f]pyrido[1,2-a]indole-6,11-dione, C23H13NO4
  39. Crystal structure of chlorido-(4-chloro-6-(p-tolyl)pyrimidine-κ2C,N)-(triphenylphosphane-κP)palladium(II), C29H23Cl2N2PPd
  40. Crystal structure of catena-poly[diaqua-bis(3,4,5,6-tetrabromo-carboxybenzoato-κ1O)-(μ2-4,4′-bipyridine-κ2N:N′)cobalt(II)], C26H14Br8CoN2O10
  41. Crystal structure of catena-poly[dibenzyl-dichlorido-(μ2-[4,4′-bipyridine]1,1′-dioxide-κ2O:O′)tin(IV)], C24H22Cl2N2O2Sn
  42. Crystal structure of benzyl-chlorido-(4-chloro-N-[(2-oxidophenyl)methylidene]benzenecarbohydrazonato)-methanol-tin(IV), C22H20Cl2N2O3Sn
  43. Crystal structure of catena-poly[triaqua-(1,3-di(1H-imidazol-1-yl)benzene-κ2N:N′)-(3-nitrophthalato-κ1O)cobalt(II)] — water (2/3), C20H22N5O10.5Co
  44. Crystal structure of (3R,5R,8R,9R,10R,12R,13R,14R)-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol, C30H52O3
  45. Crystal structure of 3-(3-(4-carboxyphenyl)ureido)pyridin-1-ium perchlorate, C26H24Cl2N6O14
  46. Crystal structure of 8-hydroxy-2-methylquinolin-1-ium chloride dihydrate, C10H14ClNO3
  47. Crystal structure of (dibenzyl sulphoxide-κO)dibromido-bis(4-bromobenzyl-κC)tin(IV), C28H26Br4OSSn
  48. Crystal structure of bromido-tri(4-chlorophenyl-κ1C)-(ethanol-κ1O)tin(IV) — 4,4′-dimethyl-2,2′-bipyridine (2/1), C52H48Br2Cl6N2O2Sn2
  49. Crystal structure of 2-butyl-6-(ethylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione, C18H20N2O2
  50. Crystal structure of (4-chloro-N-[(2-oxido-5-chlorophenyl)methylidene] benzene-carbohydrazonato-κ3N,O,O′)bis(2-fluorobenzyl)tin(IV), C28H20Cl2F2N2O2Sn
  51. Crystal structure of aqua-chlorido-(4-fluorobenzyl-κC)-(N′-(4-methoxy-2-oxidobenzylidene)-3-hydroxy-2-naphthohydrazidato-κ3N,O,O′)tin(IV), C26H22ClFN2O5Sn
  52. Crystal structure of catena-poly[tri(4-chlorophenyl)-(μ2-hydroxido)tin(IV)] – 2-propanol (1/1), C21H21Cl3O2Sn
  53. Crystal structure of bromido-dimethyl-4-tolyl-(triphenylphosphine oxide)tin(IV), C27H28BrOPSn
  54. Crystal structure of 2-(bis(2-hydroxyethyl)ammonio)ethane-1-sulfonate, C6H15NO5S
  55. Crystal structure of bis[triaqua-(μ2-1,2-di(4-pyridyl)ethylene-κ2N:N′)-(4-sulfonatobenzoato-κ2O,O′)zinc(II)], C13H15NO8SZn
  56. Crystal structure of 2-((2-(3-hydroxy-7-methylene-2,3-dihydro-7H-furo[3,2-g]chromen-2-yl)propan-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol – a marmesin derivative, C20H24O10
  57. Crystal structure of octa(4-chlorobenzyl)-dichlorido-bis(μ2-methanolato)-bis(μ3-oxo)-tetratin(IV), C58H54Cl10O4Sn4
  58. Crystal structure of iodido-triphenyl-(triphenylphosphine oxide)tin(IV), C36H30IOPSn
  59. Crystal structure of dichlorido-bis(4-methylphenyl-κC)-bis(triphenylarsine oxide-κO)tin(IV), C50H44As2Cl2O2Sn
  60. Crystal structure of 4-benzyl-1-oxo-N-phenethyl-1H-[1,4]oxazino [4,3-b]indazole-3-carboxamide, C26H21N3O3
  61. Crystal structure of bis{(N-[(5-chloro-2-oxidophenyl)methylidene]-2-hydroxybenzenecarbohydrazonato)-dioxo-molybdenum(VI)}(μ2-4,4′-bipyridine), C38H26Cl2Mo2N6O10
  62. Crystal structure of dichlorido-octamethyl-bis(μ3-oxido)-bis(μ2-2-(phenylamino)ethanolato-κ2O:O)tetratin(IV), C24H44Cl2N2O4Sn4
  63. The crystal structure of 1-(2-(2-(imidazo[1,5-a]pyridine-4-ium)ethoxy)ethyl)-imidazo[1,5-a]pyridine-4-ium bis(hexafluorophosphate) — acetonitrile (1/1), C18H20ON4F12P2
  64. Crystal structure of cyclo[tetra(μ2-cyanido)-tetracyanido-bis(1,4,7,10-tetraazacyclododecane-κ4N,N′,N′′,N′′′)dinickel(II)dipalladium(II)] hexahydrate, C24H52N16Ni2O6Pd2
  65. Crystal structure of (dimethyl sulfoxide)-dioxido-[2-hydroxy-N′-(4-oxo-4-phenylbutan-2-ylidene)benzohydrazidato κ3N,O,O′]molybdenum(VI), C19H20MoN2O6S
  66. Crystal structure of bis(acetylacetonato-κ2O,O′)-(ethanolamine-κ2N,O)copper(II), C14H25CuNO5
  67. Crystal structure of chlorido-diphenyl-(isopropyl(propyl)carbamodithioato-κ2S,S′)tin(IV), C19H24ClNS2Sn
  68. The crystal structure of bis(imidazole-1-yl)methane monohydrate, C7H10N4O
  69. The crystal structure of bis(4-nitroimidazole-1-1yl)methane, C7H6N6O4
  70. Crystal structure of di(naphthalen-2-yl)sulfane, C20H14S
  71. Crystal structure of 3-acetyl-6-bromo-4-hydroxy-2H-chromen-2-one, C11H7BrO4
  72. Crystal structure of N′2,N′6-bis((E)-1-(pyrazin-2-yl)ethylidene)pyridine-2,6-dicarbohydrazide — methanol (1/2), C21H25N9O4
  73. The crystal structure of 3-nitro-4-(p-tolylamino)-2H-chromen-2-one, C16H12N2O4
  74. The crystal structure of 1,2-bis((4-methoxyphenyl)ethynyl)benzene, C24H18O2
  75. Crystal structure of a low-temperature (100 K) polymorph of catena-poly[(μ2-4,4′-bipyridine-κ2N,N′)-bis(O,O′-diethyldithiophosphato-κ1S)zinc(II)], C18H28N2O4P2S4Zn
  76. The pseudosymmetric low temperature polymorph of catena-poly[(μ2-4,4′-bipyridyl-κN,N′)-bis(O,O′-diethyldithiophosphato-κS)-cadmium(II)], {C18H28CdN2O4P2S4}n
  77. Crystal structure of 3-iodophthalic acid, C8H5IO4
  78. The crystal structure of tert-butyl (tert-butoxy(oxo)methyl)(5-bromo-2-fluorophenyl)carbamate, C16H21BrFNO4
  79. The crystal structure of bis(μ2-5,7-dichloroquinolin-8-olato-κ3N,O:O)-tetrakis(5,7-dichloroquinolin-8-olato-κ2N,O)bis(methanol-κ1O)dieuropium(III) — toluene (1/1), C63H39Cl12Eu2N6O8
  80. Crystal structure of dichlorido-(N′-(1-(3-ethylpyrazin-2-yl)ethylidene)-4-methoxybenzohydrazide-κ3N,N′,O)cadmium(II), C16H18N4O2Cl2Cd
  81. A redetermination of the crystal structure of catena-poly[(bis(O,O′-isopropyl dithiophosphato-κ2S,S′)-(μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N,N′)cadmium(II)], {C24H38CdN4O4P2S4}n
https://doi.org/10.1515/ncrs-2019-0552
Creative Commons
BY 4.0

Articles in the same Issue

  1. 10.1515/ncrs-2020-frontmatter1
  2. The crystal structure of 3,5-dicarboxybenzenaminium perchlorate monohydrate, C8H8ClNO9
  3. The crystal structure of poly[(m4-4-bromoisophthalato-κ4O: O′:O′′:O′′′)zinc(II)], C8H3BrO4Zn
  4. Crystal structure of (E)-2-(2-chloro-6-hydroxybenzylidene)hydrazine-1-carbothioamide, C8H8ClN3O4S
  5. Crystal structure of 1,1′-methylenebis(3-ethyl-1H-imidazol-3-ium) bis(hexafluorophosphate(V)), C11H18F12N4P2
  6. The crystal structure of hexakis(1-isopropyl-1H-imidazole-κ1N)copper(II) dichloride, C36H58Cl2CuN12
  7. Crystal structure of catena-poly[μ2-4,4′-bipyridine-κ2N:N′)-tetrakis(μ2-2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-κ2O:O′)dicobalt(II)], C19H10Cl6CoN3O6
  8. Crystal structure of (E)-1-(4-(((E)-2-bromo-6-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H15BrN2O2
  9. Crystal structure of ethyl 2-methyl-4-(5-methylthiophen-2-yl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C18H21NO3S
  10. The crystal structure of 5-bromo-2-(1-methyl-1H-tetrazol-5-yl)pyridine, C7H6BrN5
  11. Crystal structure of Bis(acetato-κ2O,O′)-bis[4-(dimethylamino)pyridine-κN]nickel(II), C18H26N4NiO4
  12. Crystal structure of (E)-3-chloro-2-(((4-chlorophenyl)imino)methyl)phenol, C13H9Cl2NO
  13. The co-crystal structure of (17b)-estra-1,3,5(10)-triene-3,17diol – acetamide (1/1), a Z′ = 4 structure, C20H29NO3
  14. Crystal structure of 3-(3-(pyridin-3-yl)ureido)benzoic acid, C13H11N3O3
  15. The crystal structure of 1,1′-(9-ethyl-9H-carbazole-3,6-diyl)bis(3-ethyl-1H-imidazol-3-ium) bis(hexafluorophosphate(IV)), C24H27N5F12P2
  16. The crystal structure of 2-bromoisophthalic acid, C8H5BrO4
  17. The crystal structure of 13-ethoxycarbonyl-9-methyl-4-chlor-11-thioxo-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2,4,6-triene, C14H15ClN2O3S
  18. The crystal structure of (E)-4-((4-(diethylamino)benzylidene)amino)-N,N-diphenylaniline, C29H29N3
  19. Crystal structure of 2-(3-(2-(4-phenylpiperazin-1-yl)ethyl)benzyl)isoindoline-1,3-dione, C27H27N3O2
  20. Crystal structure of 2-ethoxy-6-((E)-((3-(((E)-3-ethoxy-2-hydroxybenzylidene)amino)-2-hydroxypropyl)iminio)methyl)phenolate, C21H26N2O5
  21. The crystal structure of catena-poly(μ2-4,4′-bipyridine-κ2N:N′)-tetrakis(μ2-2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-κ2O:O′)dinickel(II)], C19H10Cl6N3NiO6
  22. Crystal structure of hexakis(μ2-azido-κ2N:N)-diazido-κ1N-tetrakis(phenanthroline-κ2N,N′)tetrazinc(II), C48H32N32Zn4
  23. Synthesis and crystal structure of bis{2-bromo-6-(((4-(1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O}cobalt(II)–dichloromethane(1/1), C34H32Br2Cl4CoN4O4
  24. Crystal structure of (E)-3-chloro-2-(((4-nitrophenyl)imino)methyl)phenol, C13H9ClN2O3
  25. Crystal structure of aqua-bis(5-bromo-6-methyl-picolinato-κ2N,O)zinc(II) dihydrate, C14H16Br2N2O7Zn
  26. Crystal structure of biaqua(2,2′-bipyridine-4,4′-dicarboxylato-κ2N,N′)(pyridine-2,6-dicarboxylato-κ3O,N,O′)nickel(II) hydrate, C19H15N3NiO10
  27. Synthesis and crystal structure of bis(2-(((4-(1-(ethoxyimino)ethyl)phenyl)imino)methyl)-5-fluorophenolato-κ2N,O)zinc(II) - methanol (1/1), C33H32F2N4O4Zn
  28. Crystal structure of tetraaqua-bis(μ2-5-aminoisophthalato-κ3N:O,O′)-bis(4,4′-dipyridylsulfide-κ1N)dizinc(II), C36H34N6O12S2Ni2
  29. Crystal structure of (1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)palladium(II) tetracyanonickelate(II), C14H24N8NiPd
  30. The crystal structure of 3-benzyl-1-((8-(benzyloxy)quinolin-2-yl)methyl)-1H-imidazol-3-ium hexafluorophosphate, C27H24N3OF6P
  31. Crystal structure of 1-(4-chloro-2-hydroxy-5-iodophenyl)ethan-1-one, C8H6ClIO2
  32. Crystal structure of hexaaquamagnesium(II) bis((E)-4-((4-(dimethylamino)phenyl)diazenyl)benzenesulfonate), C28H40MgN6O12S2
  33. Crystal structure of the coordination polymer catena-poly[(1,2-di(pyridin-4-yl)ethane-κN)-(μ2-2-nitroisophthalato-κ2O:O′)zinc(II)], C20H17N3O7Zn
  34. Crystal structure of catena-{[tri-aqua-di-sodium bis(2-{[n-butyl(methyl)carbamothioyl]sulfanyl}acetate)]}n, [C16H34N2Na2O7S4]n
  35. The crystal structure of diaqua-bis(μ2-3-((3-acetyl-5-carboxyphenyl)oxidophosphoryl)-5-carboxybenzoato-κ2O:O′)bis(5,5′-dimethyl-2,2′-bipyridine-k2N,N′)zinc(II), C56H46N4O22P2Zn2
  36. Crystal structure of N′,2-bis((E)-2-chloro-6-hydroxybenzylidene)hydrazine-1-carbothiohydrazide, C15H12Cl2N4O2S
  37. Crystal structure of 2-[(1E)-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]iminiumyl}methyl]-5-(dodecyloxy)benzen-1-olate, C23H39NO5
  38. Crystal structure of 12-(2-hydroxybenzoyl)benzo[f]pyrido[1,2-a]indole-6,11-dione, C23H13NO4
  39. Crystal structure of chlorido-(4-chloro-6-(p-tolyl)pyrimidine-κ2C,N)-(triphenylphosphane-κP)palladium(II), C29H23Cl2N2PPd
  40. Crystal structure of catena-poly[diaqua-bis(3,4,5,6-tetrabromo-carboxybenzoato-κ1O)-(μ2-4,4′-bipyridine-κ2N:N′)cobalt(II)], C26H14Br8CoN2O10
  41. Crystal structure of catena-poly[dibenzyl-dichlorido-(μ2-[4,4′-bipyridine]1,1′-dioxide-κ2O:O′)tin(IV)], C24H22Cl2N2O2Sn
  42. Crystal structure of benzyl-chlorido-(4-chloro-N-[(2-oxidophenyl)methylidene]benzenecarbohydrazonato)-methanol-tin(IV), C22H20Cl2N2O3Sn
  43. Crystal structure of catena-poly[triaqua-(1,3-di(1H-imidazol-1-yl)benzene-κ2N:N′)-(3-nitrophthalato-κ1O)cobalt(II)] — water (2/3), C20H22N5O10.5Co
  44. Crystal structure of (3R,5R,8R,9R,10R,12R,13R,14R)-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol, C30H52O3
  45. Crystal structure of 3-(3-(4-carboxyphenyl)ureido)pyridin-1-ium perchlorate, C26H24Cl2N6O14
  46. Crystal structure of 8-hydroxy-2-methylquinolin-1-ium chloride dihydrate, C10H14ClNO3
  47. Crystal structure of (dibenzyl sulphoxide-κO)dibromido-bis(4-bromobenzyl-κC)tin(IV), C28H26Br4OSSn
  48. Crystal structure of bromido-tri(4-chlorophenyl-κ1C)-(ethanol-κ1O)tin(IV) — 4,4′-dimethyl-2,2′-bipyridine (2/1), C52H48Br2Cl6N2O2Sn2
  49. Crystal structure of 2-butyl-6-(ethylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione, C18H20N2O2
  50. Crystal structure of (4-chloro-N-[(2-oxido-5-chlorophenyl)methylidene] benzene-carbohydrazonato-κ3N,O,O′)bis(2-fluorobenzyl)tin(IV), C28H20Cl2F2N2O2Sn
  51. Crystal structure of aqua-chlorido-(4-fluorobenzyl-κC)-(N′-(4-methoxy-2-oxidobenzylidene)-3-hydroxy-2-naphthohydrazidato-κ3N,O,O′)tin(IV), C26H22ClFN2O5Sn
  52. Crystal structure of catena-poly[tri(4-chlorophenyl)-(μ2-hydroxido)tin(IV)] – 2-propanol (1/1), C21H21Cl3O2Sn
  53. Crystal structure of bromido-dimethyl-4-tolyl-(triphenylphosphine oxide)tin(IV), C27H28BrOPSn
  54. Crystal structure of 2-(bis(2-hydroxyethyl)ammonio)ethane-1-sulfonate, C6H15NO5S
  55. Crystal structure of bis[triaqua-(μ2-1,2-di(4-pyridyl)ethylene-κ2N:N′)-(4-sulfonatobenzoato-κ2O,O′)zinc(II)], C13H15NO8SZn
  56. Crystal structure of 2-((2-(3-hydroxy-7-methylene-2,3-dihydro-7H-furo[3,2-g]chromen-2-yl)propan-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol – a marmesin derivative, C20H24O10
  57. Crystal structure of octa(4-chlorobenzyl)-dichlorido-bis(μ2-methanolato)-bis(μ3-oxo)-tetratin(IV), C58H54Cl10O4Sn4
  58. Crystal structure of iodido-triphenyl-(triphenylphosphine oxide)tin(IV), C36H30IOPSn
  59. Crystal structure of dichlorido-bis(4-methylphenyl-κC)-bis(triphenylarsine oxide-κO)tin(IV), C50H44As2Cl2O2Sn
  60. Crystal structure of 4-benzyl-1-oxo-N-phenethyl-1H-[1,4]oxazino [4,3-b]indazole-3-carboxamide, C26H21N3O3
  61. Crystal structure of bis{(N-[(5-chloro-2-oxidophenyl)methylidene]-2-hydroxybenzenecarbohydrazonato)-dioxo-molybdenum(VI)}(μ2-4,4′-bipyridine), C38H26Cl2Mo2N6O10
  62. Crystal structure of dichlorido-octamethyl-bis(μ3-oxido)-bis(μ2-2-(phenylamino)ethanolato-κ2O:O)tetratin(IV), C24H44Cl2N2O4Sn4
  63. The crystal structure of 1-(2-(2-(imidazo[1,5-a]pyridine-4-ium)ethoxy)ethyl)-imidazo[1,5-a]pyridine-4-ium bis(hexafluorophosphate) — acetonitrile (1/1), C18H20ON4F12P2
  64. Crystal structure of cyclo[tetra(μ2-cyanido)-tetracyanido-bis(1,4,7,10-tetraazacyclododecane-κ4N,N′,N′′,N′′′)dinickel(II)dipalladium(II)] hexahydrate, C24H52N16Ni2O6Pd2
  65. Crystal structure of (dimethyl sulfoxide)-dioxido-[2-hydroxy-N′-(4-oxo-4-phenylbutan-2-ylidene)benzohydrazidato κ3N,O,O′]molybdenum(VI), C19H20MoN2O6S
  66. Crystal structure of bis(acetylacetonato-κ2O,O′)-(ethanolamine-κ2N,O)copper(II), C14H25CuNO5
  67. Crystal structure of chlorido-diphenyl-(isopropyl(propyl)carbamodithioato-κ2S,S′)tin(IV), C19H24ClNS2Sn
  68. The crystal structure of bis(imidazole-1-yl)methane monohydrate, C7H10N4O
  69. The crystal structure of bis(4-nitroimidazole-1-1yl)methane, C7H6N6O4
  70. Crystal structure of di(naphthalen-2-yl)sulfane, C20H14S
  71. Crystal structure of 3-acetyl-6-bromo-4-hydroxy-2H-chromen-2-one, C11H7BrO4
  72. Crystal structure of N′2,N′6-bis((E)-1-(pyrazin-2-yl)ethylidene)pyridine-2,6-dicarbohydrazide — methanol (1/2), C21H25N9O4
  73. The crystal structure of 3-nitro-4-(p-tolylamino)-2H-chromen-2-one, C16H12N2O4
  74. The crystal structure of 1,2-bis((4-methoxyphenyl)ethynyl)benzene, C24H18O2
  75. Crystal structure of a low-temperature (100 K) polymorph of catena-poly[(μ2-4,4′-bipyridine-κ2N,N′)-bis(O,O′-diethyldithiophosphato-κ1S)zinc(II)], C18H28N2O4P2S4Zn
  76. The pseudosymmetric low temperature polymorph of catena-poly[(μ2-4,4′-bipyridyl-κN,N′)-bis(O,O′-diethyldithiophosphato-κS)-cadmium(II)], {C18H28CdN2O4P2S4}n
  77. Crystal structure of 3-iodophthalic acid, C8H5IO4
  78. The crystal structure of tert-butyl (tert-butoxy(oxo)methyl)(5-bromo-2-fluorophenyl)carbamate, C16H21BrFNO4
  79. The crystal structure of bis(μ2-5,7-dichloroquinolin-8-olato-κ3N,O:O)-tetrakis(5,7-dichloroquinolin-8-olato-κ2N,O)bis(methanol-κ1O)dieuropium(III) — toluene (1/1), C63H39Cl12Eu2N6O8
  80. Crystal structure of dichlorido-(N′-(1-(3-ethylpyrazin-2-yl)ethylidene)-4-methoxybenzohydrazide-κ3N,N′,O)cadmium(II), C16H18N4O2Cl2Cd
  81. A redetermination of the crystal structure of catena-poly[(bis(O,O′-isopropyl dithiophosphato-κ2S,S′)-(μ2-1,2-bis(3-pyridylmethylene)hydrazine-κ2N,N′)cadmium(II)], {C24H38CdN4O4P2S4}n
Sign up now to receive a 20% welcome discount
Institutional Access
How does access work?
Have an idea on how to improve our website?
Please write us.
© 2025 De Gruyter Brill
Downloaded on 9.12.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2019-0552/html
Scroll to top button