Startseite Crystal structure of (cyclohexane-1,4-diammonium) 4-[(4-carboxylatophenyl)disulfanyl]benzoate dimethylsulphoxide hydrate (1/1/1/1), [C6H16N2]2+[C14H8O4S2]2−⋅C2H6OS⋅H2O
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Crystal structure of (cyclohexane-1,4-diammonium) 4-[(4-carboxylatophenyl)disulfanyl]benzoate dimethylsulphoxide hydrate (1/1/1/1), [C6H16N2]2+[C14H8O4S2]2−⋅C2H6OS⋅H2O

  • Sang Loon Tan und Edward R. T. Tiekink EMAIL logo
Veröffentlicht/Copyright: 21. September 2019
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 234 Heft 6

Abstract

C22H32N2O6S3, triclinic, P1̄ (no. 2), a = 6.1543(1) Å, b = 14.4991(2) Å, c = 15.3859(3) Å, α = 64.545(2)°, β = 81.828(1)°, γ = 89.505(1)°, V = 1224.93(4) Å3, Z = 2, Rgt(F) = 0.0290, wRref(F2) = 0.0787, T = 100 K.

CCDC no.: 1945352

The molecular structures comprising the asymmetric unit are 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 × 0.06 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:3.12 mm−1
Diffractometer, scan mode:XtaLAB Synergy, ω
θmax, completeness:76.4°, >99%
N(hkl)measured, N(hkl)unique, Rint:30970, 5103, 0.037
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4683
N(param)refined:324
Programs:CrysAlisPRO [1], SHELX [2], [3], WinGX/ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
S10.90210(5)1.15089(2)0.04074(2)0.01692(9)
S21.03810(5)1.02360(2)0.13167(2)0.01706(9)
S30.63431(6)0.05256(3)0.66794(3)0.02236(9)
O10.07177(16)1.31298(8)0.26879(8)0.0207(2)
O20.27333(16)1.24570(8)0.38903(7)0.0199(2)
O30.30020(16)0.65920(8)0.16828(8)0.0205(2)
O40.56915(16)0.56263(7)0.23725(8)0.0202(2)
O50.7754(2)0.14306(10)0.65425(9)0.0382(3)
O1W0.55760(18)0.38313(9)0.40157(8)0.0250(2)
H1W0.557(4)0.4379(11)0.3506(11)0.037*
H2W0.480(3)0.3392(13)0.3952(16)0.037*
N1−0.00784(19)0.52137(9)0.17650(8)0.0154(2)
H1N0.013(3)0.4539(8)0.2122(11)0.018*
H2N0.103(2)0.5621(12)0.1772(12)0.018*
H3N−0.1389(19)0.5387(13)0.1995(12)0.018*
N20.9334(2)0.31328(9)0.48360(9)0.0172(2)
H4N0.817(2)0.3347(13)0.4496(12)0.021*
H5N1.039(2)0.2941(13)0.4476(12)0.021*
H6N0.886(3)0.2574(10)0.5407(9)0.021*
C10.2349(2)1.26793(10)0.30319(10)0.0163(3)
C20.3999(2)1.23624(10)0.23985(10)0.0151(3)
C30.3533(2)1.24200(10)0.15154(10)0.0165(3)
H30.21651.26590.13130.020*
C40.5045(2)1.21327(10)0.09278(10)0.0168(3)
H40.47061.21670.03320.020*
C50.7062(2)1.17940(10)0.12212(10)0.0155(3)
C60.7552(2)1.17368(10)0.20995(10)0.0165(3)
H60.89281.15070.22980.020*
C70.6021(2)1.20170(10)0.26833(10)0.0164(3)
H70.63541.19730.32840.020*
C80.8590(2)0.91885(10)0.14953(10)0.0145(3)
C90.6600(2)0.92785(10)0.11397(10)0.0161(3)
H90.60800.99350.07870.019*
C100.5383(2)0.83991(10)0.13053(10)0.0155(3)
H100.40290.84600.10610.019*
C110.6120(2)0.74294(10)0.18245(9)0.0142(3)
C120.8092(2)0.73554(10)0.21943(10)0.0163(3)
H120.85940.66990.25620.020*
C130.9330(2)0.82253(11)0.20328(10)0.0168(3)
H131.06710.81650.22870.020*
C140.4829(2)0.64774(10)0.19709(9)0.0149(3)
C15−0.0182(2)0.53829(10)0.07443(9)0.0141(3)
H15−0.05730.61030.03640.017*
C160.2064(2)0.52265(10)0.02785(10)0.0152(3)
H16A0.25250.45340.06790.018*
H16B0.31670.57340.02530.018*
C170.1967(2)0.53471(10)−0.07528(10)0.0156(3)
H17A0.16570.6061−0.11700.019*
H17B0.34090.5203−0.10310.019*
C181.0182(2)0.39790(10)0.50289(10)0.0150(3)
H181.15810.37800.53060.018*
C190.8508(2)0.41634(10)0.57622(10)0.0161(3)
H19A0.82650.35380.63860.019*
H19B0.70870.43210.55130.019*
C200.9343(2)0.50546(10)0.59297(10)0.0158(3)
H20A0.82240.51860.63870.019*
H20B1.07010.48730.62270.019*
C210.3953(3)0.10143(16)0.61431(14)0.0408(4)
H21A0.31390.13720.64890.061*
H21B0.30160.04480.61880.061*
H21C0.43900.14920.54570.061*
C220.7633(3)0.01471(15)0.57737(14)0.0395(4)
H22A0.78470.07410.51360.059*
H22B0.6695−0.03840.57530.059*
H22C0.9061−0.01220.59360.059*

Source of material

The title salt mixed solvate was prepared through solvent drop grinding of 4-mercaptobenzoic acid (Acros, Geel, Antwerp, Belgium) (0.154 g, 1 mmol) and N,N′-bis((pyridine-2-yl)methylene)-cyclohexane-1,4-diamine [5] (0.292 g, 1 mmol) in a 1:1 molar ratio. The mixture was ground for 15 min in the presence of a few drops of methanol which lead to a beige slurry. The slurry was taken up in dimethylsulphoxide (2 mL) and carefully layered with benzene (2 mL). Colourless crystals formed after a week. M.pt: 410.8–412.1 K. IR (Bruker Vertex 70v, cm−1): 3065–2854(w) ν(C—H), 1675(m) ν(C=O), 1589(s)–1432(s) ν(C=C), 1376(s) ν(C—N), 755(s) δ(C=C).

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- and N-bound H atoms were located in difference Fourier maps but were refined with distance restraints of O—H = 0.84 ± 0.01 Å and N—H = 0.91 ± 0.01 Å, respectively, and with Uiso(H) set to 1.5Ueq(O) and 1.2Ueq(N), respectively.

Comment

The isolation and crystallographic characterization of the title salt mixed solvate came about during recent co-crystallization studies of isomeric n-mercaptobenzoic acid co-formers [6], [7], [8], [9], [10], for n = 2, 3 and 4, as well as of isomeric Schiff bases appended with pyridyl donors, i.e. N,N′-bis((pyridine-n-yl)methylene)cyclohexane-1,4-diamines [5], again for n = 2, 3 and 4 [8], [9], [10], [11]. When these co-formers are combined in co-crystallization trials, each undergoes chemical reaction. For example, 2-mercaptobenzoic acid undergoes oxidation to form the disulfide 2-[(2-carboxyphenyl)disulfanyl]benzoic acid (2,2′-dithiodibenzoic acid; 2-DTBA) or salts thereof [6], [7], [8], [9], [10]; the instability of this co-former is well documented [7], [12], [13]. Thus far, in the case when n = 4, the Schiff base has been observed to decompose/react when co-crystallized with 2-mercaptobenzoic acid, leading to a cyclohexane-1,4-diammonium di-cation [9], [11]. A more spectacular outcome was noted when the Schiff base with n = 2 was co-crystallized with 2-mercaptobenzoic acid whereby the original Schiff based was converted to a 2-(4-ammoniocyclohexyl)-3-(pyridin-2-yl)imidazo[1,5-a]pyridin-2-ylium di-cation [8]. In on-going investigations in this area, herein the title salt mixed solvate is described whereby the original 4-mercaptobenzoic acid is present as the di-anion of 4-DTBA, and the original Schiff base with n = 4 is present as a cyclohexane-1,4-diammonium di-cation. The salt co-crystallized as a hydrate, dimethylsulphoxide mixed solvate.

The molecular structures of the five-component crystal are shown in the figure (70% probability displacement ellipsoids with unlabelled atoms for the N1- and N2-di-cations being −x, 1 − y, −z and 2 − x, 1 − y, 1 − z, respectively). The product comprises two independent cyclohexane-1,4-diammonium di-cations, each located about a centre of inversion, a 4-[(4-carboxylatophenyl)disulfanyl]benzoate di-anion, and a molecule each of dimethylsulphoxide (DMSO) and water. The di-cation/di-anion assignments are confirmed based on the pattern of hydrogen bonding in the crystal, as discussed in detail below, and in the closeness of the C1—O1, O2 [1.2478(17), 1.2750(17) Å] and C14—O3, O4 [1.2505(17), 1.2699(17) Å] bond lengths. Each of the centrosymmetric di-cations adopts a chair conformation so that the 1,4-ammonium groups have an anti-disposition. The di-anion is twisted as seen in the C5—S1—S2—C8 torsion angle of 85.47(7)°, and in the dihedral angle between the two phenyl rings of 78.39(7)°. To a first approximation, the carboxylate groups are co-planar with the phenyl rings which they are attached with the O1-carboxylate group exhibiting a greater twist out of the plane. This is quantified in the values of the O1—C1—C2—C7 [169.05(12)°] and O4—C14—C11—C10 [173.76(12)°] torsion angles.

Significant hydrogen bonding interactions contribute to the cohesion of the molecular packing. Each of the six ammonium and two water hydrogen atoms forms donor interactions to an oxygen acceptor (carboxylate-O, water-O and DMSO-O). The N1-ammonium cation forms charge-assisted hydrogen bonds to carboxylate-O atoms exclusively, forming a single link to three different carboxylate residues [N1—H1n⋯O1i: H1n⋯O1i = 1.900(14) Å, N1⋯O1i = 2.8053(18) Å with angle at H1n = 171.6(14)°; N1—H2n⋯O3: H2n⋯O3 = 1.814(17) Å, N1⋯O3 = 2.7173(17) Å with angle at H2n = 171.4(16)° and N1—H3n⋯O4ii: H3n⋯O4ii = 1.885(13) Å, N1⋯O4ii = 2.7876(16) Å with angle at H3n = 170.5(17)° for symmetry operations (i) x, −1 + y, z and (ii) −1 + x, y, z]. By contrast, the N2-ammonium cation forms charge-assisted hydrogen bonds to disparate oxygen atoms, namely water-O, carboxylate-O and DMSO-O atoms [N2—H4n⋯O1w: H4n⋯O1w = 1.860(14) Å, N2⋯O1w = 2.7673(17) Å with angle at H4n = 168.6(15)°; N2—H5n⋯O2iii: H5n⋯O2iii = 1.882(16) Å, N2⋯O2iii 2.7890(17) Å with angle at H5n = 172.2(15)° and N2—H6n⋯O5: H6n⋯O5 = 1.859(14) Å, N2⋯O5 = 2.7705(18) Å with angle at H6n = 176.8(18)° for (iii) 1 + x, −1 + y, z]. Finally, the water-O—H forms donor interactions to carboxylate-O atoms [O1w—H1w⋯O4: H1w⋯O4 = 1.890(16) Å, O1w⋯O4 = 2.7325(16) Å with angle at H1w = 177.2(18)° and O1w—H2w⋯O2i: H2w⋯O2i = 1.91(2) Å, O1w⋯O2i = 2.7487(17) Å with angle at H2w = 172.5(19)°]. Globally, the di-anions and water molecules establish a three-dimensional framework with the DMSO molecules lying in channels parallel to the a axis direction.

The Hirshfeld surfaces, as well as the two-dimensional fingerprint plot (full and delineated), were also calculated using literature procedures [14] and Crystal Explorer 17 [15]. Such an analysis has proved useful in distinguishing multiple molecules in a crystallographic asymmetric unit [16]. Overall, for the asymmetric unit illustrated in the figure, there are five types of contacts making a significant contribution (>1%) to the Hirshfeld surface: H⋯H [45.8%], O⋯H/H⋯O [27.4%], C⋯H/H⋯C [14.3%], S⋯H/H⋯S [6.0%] and S⋯C/C⋯S [4.4%]. To a first approximation, these values mirror those in the analogous 2-DTBA structure with DMF [9] rather than DMSO, i.e. H⋯H [45.7%], O⋯H/H⋯O [30.1%], C⋯H/H⋯C [16.0%], S⋯H/H⋯S [5.8%] and S⋯C/C⋯S [0.5%]. The only differences are seen in the O⋯H/H⋯O, C⋯H/H⋯C and S⋯C/C⋯S contacts, i.e. variations of up to a few percent. The analysis of the contacts formed by the two independent di-cations in the title salt prove instructive. For the N1-di-cation, four different types of contacts are evident, namely H⋯H [51.8%], O⋯H/H⋯O [30.9%], C⋯H/H⋯C [14.3%] and S⋯H/H⋯S [2.9%]. Quite different percentage contributions are seen for the N2-di-cation: H⋯H [59.3%], O⋯H/H⋯O [36.4%] and C⋯H/H⋯C [4.2%], i.e. with significant increases in the H⋯H and O⋯H/H⋯O contacts at the expense of the C⋯H/H⋯C and S⋯H/H⋯S contacts. It is argued that these differences are systematic and correlate with the nature of the N—H⋯O hydrogen bonding patterns. Thus, a tighter network of hydrogen bonds are apparent for the N1-di-cation which forms three charge-assisted ammonium-N—H⋯O(carboxylate) interactions. By contrast, the N2-dication forms charge-assisted hydrogen bonds to disparate oxygen atoms, namely to carboxylate-O, water-O and DMSO-O acceptors. With a less-tight, more diffuse, hydrogen bonding arrangement, the percentage of O⋯H/H⋯O surface contacts increases at the expenses of weaker interactions. A similar analysis of the individual di-cations in the DMF analogue [9] was also conducted. Here, for the N1-di-cation which forms two charge-assisted ammonium-N—H⋯O(carboxylate) interactions as well as a charge-assisted hydrogen bond to the O(DMF), the percentage contributions compute to H⋯H [56.5%], O⋯H/H⋯O [33.2%], C⋯H/H⋯C [9.6%] and S⋯H/H⋯S [0.8%]. For the N2-di-cation, systematic variations are again apparent with the percentage contributions being H⋯H [52.3%], O⋯H/H⋯O [43.4%], C⋯H/H⋯C [2.4%] and S⋯H/H⋯S [1.6%]. As well as forming two charge-assisted ammonium-N—H⋯O(carboxylate) interactions, this cation forms a charge-assisted hydrogen bond to a water molecule, which also forms donor interactions to carboxylate-O and DMF-O atoms, leading to a more open arrangement and hence, greater percentage contribution by O⋯H/H⋯O surface contacts. Finally, it is noteworthy that there is a systematic variation in the percentage contributions afforded by the H⋯H and O⋯H/H⋯O surface contacts in that values in the DMF-containing structure, lie between the extremes of the DMSO-containing structure.

Acknowledgements

Sunway University Sdn Bhd is thanked for financial support of this work through Grant No. STR-RCTR-RCCM-001–2019.

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Received: 2019-07-11
Accepted: 2019-08-05
Published Online: 2019-09-21
Published in Print: 2019-11-26

©2019 Sang Loon Tan et al., published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Frontmatter
  2. Crystal structure of [aqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N3,N3′,O4,O4′] zinc(II)] monohydrate, C16H10N4O9Zn⋅H2O
  3. Crystal structure of ethyl 3-(4-methoxyphenyl)-5-methylcarbamoyl-1H-pyrazole-4-carboxylate, C15H17N3O4
  4. 7-(4-Fluorobenzylidene)-3-(4-fluorophenyl)-N-phenyl-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbothioamide–dimethylformamide (2/1), C27H23F2N3S, 0.5(C3H7NO)
  5. Crystal structure of 4,4′-(hydrazonomethylene)diphenol dihydrate, C13H16N2O4
  6. Crystal structure of 4-methoxyphenyl-3-phenylpropiolate, C16H12O3
  7. Crystal Structure of tris(tetrakis{1-vinyl-1H-imidazole-κN}copper(II)) bis[tri-μ2-bromido-tetrabromido-bis(1-vinyl-1H-imidazole-κN)tetracopper(I)], C80H96N32Cu11Br14
  8. Crystal structure of (E)-2-(3,6-bis(diethylamino)-9H-xanthen-9-yl)-N′-(quinoxalin-2-ylmethylene)benzohydrazide, C37H36N6O2
  9. Crystal structure of 4-(1-phenylimidazo[1,5-a]pyridin-3-yl)benzoic acid (C20H14N2O2)
  10. Crystal structure of 3-fluoro-3-methyl-1-((2-nitrophenyl)sulfonyl)-5,5-diphenylpiperidine, C24H23FN2O4S
  11. Crystal structure of dimethyl 3,12-dibenzyl-6,10-diphenyl-3,12-diazapentacyclo [6.3.1.02.7.04.11.05.9]-dodecane-7,11-dicarboxylate — acetone (2/1), C40H38N2O2 ⋅ 0.5C3H6O
  12. Crystal structure of poly[(μ2-2-(1H-1,2,4-triazol-1-yl)benzoato-κ4O:O′:N:N′)silver(I)] monohydrate, C9H8AgO3N3
  13. Crystal structure of poly[(μ2-9H-carbazole-3,6-dicarboxylate-κ4O1,O2:O3,O4)(μ2-1,3-di(pyridin-4-yl)propane-κ2N:N′)cadmium(II)]monohydrate, C27H23N3O5Cd
  14. The synthesis and crystal structure of bis(2-(benzo[d]thiazol-2-yl)-5-methylbenzen-1-ido-κ2C,N)-(N,N′-diethyldithiocarbamato-κ2S,S′)iridium(III), C33H30N3S4Ir
  15. The crystal structure of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfonyl)-1H-pyrazole-3-carboxamide, C12H6N4Cl2F6O3S
  16. Synthesis and crystal structure of poly[(μ2-nitrato-κ4O,O′:O′,O′′)-nitrato-κO-(μ2-1,4-bis((1H-imidazol-1-yl)methyl)benzene-κ2N:N′)cadmium(II)], C14H14N6O6Cd
  17. Crystal structure of ethyl (Z)-(4-oxo-4-phenylbut-2-en-2-yl)glycinate, C14H17NO3
  18. Halogen bonds in the crystal structure of 5-bromo-3,4′-bipyridine – 1,4-diiodotetrafluorobenzene (2/1), C26H14Br2F4I2N4
  19. Crystal structure of bis(2,2′-bipyridine-κ2N,N′)-tetrakis(μ2-3-(phenylsulfonamido)propanoato-κ2O:O′)-bis(3-(phenylsulfonamido)propanoato-κ2O,O′)digadolinium(III) – 2,2′-bipyridine (1/1), C84H84Gd2N12O24S6
  20. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ2O:O′)bis(μ2-pyrazin-κ2N:N′)silver(I)], C14H16Ag2N5O8S2
  21. The crystal structure of 1,6-di-tert-butyl-1,1,3,3,4,4,6,6-octamethyl-2,2,5,5-tetrakis (trimethylsilyl)hexasilane, C28H78Si10
  22. Crystal structure of discandium triruthenium tetrasilicide, Sc2Ru3Si4
  23. Crystal structure of poly[(μ2-4-amino-1,5-naphthalenedisulfonato-κ4O,N:O′, N′)bis(μ2-hexamethylenetetramino-κ2N;N′)silver(I)], {C22H30Ag2N9O6S2}n
  24. Crystal structure of diaqua[5,5′-dicarboxy-2,2′-(propane-1,3-diyl)bis(1H-imidazole-4-carboxylato-κ4O,O′,N,N′)]zinc(II) dihydrate, C13H18N4O12Zn
  25. The crystal structure of poly [(μ3-N1,N4-bis(pyridin-3-yl)cyclohexane-1,4-dicarboxamide-κ3-O:N:N′)-(p-toluenesulfonato-κ2O,O′)silver(I)], C25H27Ag1N4O5S
  26. The crystal structure of 1,2-bis(3-bromophenoxy) ethane, C14H12Br2O2
  27. The crystal structure of 4-(pyren-1-yl)butyl-3-nitrobenzoate, C27H21NO4
  28. Crystal structure of bis[(2-(4-chlorophenyl)-5-methyl-1,3-dioxane-5-carboxylato-κ1O) (5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II), C40H60Cl2N4NiO8
  29. The crystal structure of 1,5-dinitro-2,3,4-trichlorobenzene, C6H1Cl3N2O4
  30. The crystal structure of the solid solution of 3,5-dinitropyrazole and 4-chlorine-3,5-dinitropyrazole, C3H1.24Cl0.76N4O4
  31. The cocrystal structure of 4-nitropyrazole — acetic acid (1/1), C5H7N3O4
  32. The crystal structure of propan-2-one O-(2,4,6-trinitrophenyl) oxime, C9H8N4O7
  33. The crystal structure of ethyl 2-(3-(2-ethoxy-2-oxoethyl)benzo[d] thiazol-2(3H)-ylidene)acetate, C15H17NO4S
  34. Crystal structure of (acetic acid-κ1O)-bis(μ2-2-chlorobenzoato-κ2O:O′)-(2-chlorobenzoato-κ1O)-(μ2-hydroxy-κ2O:O)-bis(1,10-phenanthroline-κ2N,N′)dimanganese(II) — methanol (1/1), C48H37Cl3Mn2N4O10
  35. Crystal structure of 3-methyl-2-phenyl-1,8-naphthyridine, C15H12N2
  36. Crystal structure of chlorido-(5-acetyl-2-(5-methylpyridin-2-yl)benzen-1-ido-κ2C,N)-pyridine-κN-palladium(II), C19H17ClN2OPd
  37. Crystal structure of (4-methyl-benzoato-κ2O,O′)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, C24H45ClN4NiO7
  38. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6) 1,2,3,4,5-pentamethyl-cyclopenta-2,4-dien-1-yl(potassium, rubidium) — ammonia (1/2), [K0.3Rb0.7(18-crown-6)]Cp*⋅2 NH3, C22H45K0.3N2O6Rb0.7
  39. Crystal structure of (3E,5E)-1-((4-fluorophenyl)sulfonyl)-3,5-bis(3-nitrobenzylidene)piperidin-4-one — dichloromethane (2/1), C51H38Cl2F2N6O14S2
  40. Crystal structure of (E)-N′-((1,6-dihydropyren-1-yl)methylene)isonicotinohydrazide — methanol (1/1), C24H19N3O2
  41. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ3N,O:O′)-(μ4-hexamethylenetetramino-κ4N:N′:N′′:N′′′)disilver(I)] monohydrate, C12H21Ag2N5O8S2
  42. Crystal structure of bis(acridin-10-ium) 2,5-dihydroxyterephthalate — 2,5-dihydroxyterephthalic acid (1/1), C21H15NO6
  43. The crystal structure of 1,12-diazaperylene, C18H10N2
  44. Crystal structure of 1-(5-(4-chlorophenyl)-3-(2-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one, C17H14N2OFCl
  45. Crystal structure of (4aR,6aR,6bR,10S,12aR)-10-acetoxy-1,2,3,4, 4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a, 12b,13,14b-icosahydro-2,2,4a,6b,9,9,12a-heptamethylpicene-6a-carboxylic acid, C32H50O4
  46. The crystal structure of tetrachlorido-bis{1,3-bis(2,6-diisopropylphenyl)-1H-3λ4-imidazol-2-yl}-(μ2-pyrimidine-κ2N:N′)dipalladium(IV) — dichloromethane (1/2), C60H80Cl8N6Pd2
  47. The crystal structure of (E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-yl 4-nitrobenzoate, C22H19NO7
  48. Crystal structure of 3-methyl-N-(pyrimidin-5-ylmethyl)pyridin-2-amine, C11H12N4
  49. The crystal structure of 2,5-dichloroterephthalic acid dihydrate, C8H8Cl2O6
  50. The crystal structure of 2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine — dimethylformamide (1/1), C33H28N10O
  51. Crystal structure of N-(adamantan-1-yl)-5-(dimethylamino)naphthalene-1-sulfonamide, C22H28N2O2S
  52. Crystal structure of poly[diaqua-(μ4-4-(3,5-dicarboxy-κ1O-phenoxy)phthalato-κ3O:O′:O′)cadmium(II)], C16H12CdO11
  53. Crystal structure of poly[diaqua-bis(μ2-3-((1H-imidazol-1-yl)methyl)benzoato-κ2N:O)manganese(II)], C22H22MnN4O6
  54. Crystal structure of 9-(3-phenoxyphenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione, C25H23NO3
  55. The crystal structure of poly[(μ3-2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine-k3N:N′:N′′)-(nitrato-k2O,O)-(nitrato-k1O)zinc(II)] - N,N-dimethylacetamide (1/2), C38H39N13O8Zn
  56. Crystal structure of poly[(μ7-4-(3,5-dicarboxylatophenoxy)phthalato)-(1,10-phenanthroline-κ2N,N′)dizinc(II)], C28H14N2O9Zn2
  57. The crystal structure of methyl 2-(benzylamino)-5-(benzyloxy)benzoate, C22H21NO3
  58. Crystal structure of (1,4,8,11-tetraazacyclotetradecane)palladium(II) tetracyanoplatinate(II), C14H24N8PdPt
  59. Crystal structure of (pyridine-2-carboxylato-κ2N,O)-[2-(2-pyridyl)phenyl-κ2N,C1]palladium(II), C17H12N2O2Pd
  60. Crystal structure of (cyclohexane-1,4-diammonium) 4-[(4-carboxylatophenyl)disulfanyl]benzoate dimethylsulphoxide hydrate (1/1/1/1), [C6H16N2]2+[C14H8O4S2]2−⋅C2H6OS⋅H2O
  61. Crystal structure of the 2:1 co-crystal 2-[(2-carboxyphenyl)disulfanyl]benzoic acid – 3-bromobenzoic acid, 2(C14H10O4S2)⋅C7H5BrO2
  62. Crystal structure of chlorido-dimethyl-(phenylpiperazine-1-carbodithioato-κ2S,S′)tin(IV), C13H19ClN2S2Sn
  63. Crystal structure of (N-n-butyl, N-methyl-dithiocarbamato-κ2 S,S′)-chlorido-dimethyl-tin(IV), C8H18ClNS2Sn
  64. Crystal structure of (2,2′-bipyridyl)bis(4-bromobenzyl)dibromidotin(IV), C24H20Br4N2Sn
  65. Crystal structure of (2,2′-bipyridyl)bis(4-chlorobenzyl)dichloridotin(IV), C24H20Cl4N2Sn
  66. Crystal structure of N-methyl-N-phenyl(methylsulfanyl)carbothioamide, C9H11NS2
  67. Crystal structure of 4-phenylpiperazin-1-ium (4-phenylpiperazin-1-yl)carbothioylsulfanide, [C10H15N2][C11H13N2S2]
  68. Crystal structure of catena-{di-aqua-sodium [n-butyl(methyl)carbamothioyl]sulfanide}n, [C6H16NNaO2S2]n
  69. Crystal structure of (2-([1,1-bis(hydroxymethyl)-2-oxyethyl]iminomethyl)-5-(n-decyl)phenolato)-dimethyl-tin(IV), C23H39NO5Sn
  70. Crystal structure of 4-chloro-N′-[(1E)-(3-ethoxy-2-hydroxyphenyl)methylidene]benzohydrazide – a Z′ = 3 structure, C16H15ClN2O3
https://doi.org/10.1515/ncrs-2019-0487
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Artikel in diesem Heft

  1. Frontmatter
  2. Crystal structure of [aqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N3,N3′,O4,O4′] zinc(II)] monohydrate, C16H10N4O9Zn⋅H2O
  3. Crystal structure of ethyl 3-(4-methoxyphenyl)-5-methylcarbamoyl-1H-pyrazole-4-carboxylate, C15H17N3O4
  4. 7-(4-Fluorobenzylidene)-3-(4-fluorophenyl)-N-phenyl-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbothioamide–dimethylformamide (2/1), C27H23F2N3S, 0.5(C3H7NO)
  5. Crystal structure of 4,4′-(hydrazonomethylene)diphenol dihydrate, C13H16N2O4
  6. Crystal structure of 4-methoxyphenyl-3-phenylpropiolate, C16H12O3
  7. Crystal Structure of tris(tetrakis{1-vinyl-1H-imidazole-κN}copper(II)) bis[tri-μ2-bromido-tetrabromido-bis(1-vinyl-1H-imidazole-κN)tetracopper(I)], C80H96N32Cu11Br14
  8. Crystal structure of (E)-2-(3,6-bis(diethylamino)-9H-xanthen-9-yl)-N′-(quinoxalin-2-ylmethylene)benzohydrazide, C37H36N6O2
  9. Crystal structure of 4-(1-phenylimidazo[1,5-a]pyridin-3-yl)benzoic acid (C20H14N2O2)
  10. Crystal structure of 3-fluoro-3-methyl-1-((2-nitrophenyl)sulfonyl)-5,5-diphenylpiperidine, C24H23FN2O4S
  11. Crystal structure of dimethyl 3,12-dibenzyl-6,10-diphenyl-3,12-diazapentacyclo [6.3.1.02.7.04.11.05.9]-dodecane-7,11-dicarboxylate — acetone (2/1), C40H38N2O2 ⋅ 0.5C3H6O
  12. Crystal structure of poly[(μ2-2-(1H-1,2,4-triazol-1-yl)benzoato-κ4O:O′:N:N′)silver(I)] monohydrate, C9H8AgO3N3
  13. Crystal structure of poly[(μ2-9H-carbazole-3,6-dicarboxylate-κ4O1,O2:O3,O4)(μ2-1,3-di(pyridin-4-yl)propane-κ2N:N′)cadmium(II)]monohydrate, C27H23N3O5Cd
  14. The synthesis and crystal structure of bis(2-(benzo[d]thiazol-2-yl)-5-methylbenzen-1-ido-κ2C,N)-(N,N′-diethyldithiocarbamato-κ2S,S′)iridium(III), C33H30N3S4Ir
  15. The crystal structure of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfonyl)-1H-pyrazole-3-carboxamide, C12H6N4Cl2F6O3S
  16. Synthesis and crystal structure of poly[(μ2-nitrato-κ4O,O′:O′,O′′)-nitrato-κO-(μ2-1,4-bis((1H-imidazol-1-yl)methyl)benzene-κ2N:N′)cadmium(II)], C14H14N6O6Cd
  17. Crystal structure of ethyl (Z)-(4-oxo-4-phenylbut-2-en-2-yl)glycinate, C14H17NO3
  18. Halogen bonds in the crystal structure of 5-bromo-3,4′-bipyridine – 1,4-diiodotetrafluorobenzene (2/1), C26H14Br2F4I2N4
  19. Crystal structure of bis(2,2′-bipyridine-κ2N,N′)-tetrakis(μ2-3-(phenylsulfonamido)propanoato-κ2O:O′)-bis(3-(phenylsulfonamido)propanoato-κ2O,O′)digadolinium(III) – 2,2′-bipyridine (1/1), C84H84Gd2N12O24S6
  20. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ2O:O′)bis(μ2-pyrazin-κ2N:N′)silver(I)], C14H16Ag2N5O8S2
  21. The crystal structure of 1,6-di-tert-butyl-1,1,3,3,4,4,6,6-octamethyl-2,2,5,5-tetrakis (trimethylsilyl)hexasilane, C28H78Si10
  22. Crystal structure of discandium triruthenium tetrasilicide, Sc2Ru3Si4
  23. Crystal structure of poly[(μ2-4-amino-1,5-naphthalenedisulfonato-κ4O,N:O′, N′)bis(μ2-hexamethylenetetramino-κ2N;N′)silver(I)], {C22H30Ag2N9O6S2}n
  24. Crystal structure of diaqua[5,5′-dicarboxy-2,2′-(propane-1,3-diyl)bis(1H-imidazole-4-carboxylato-κ4O,O′,N,N′)]zinc(II) dihydrate, C13H18N4O12Zn
  25. The crystal structure of poly [(μ3-N1,N4-bis(pyridin-3-yl)cyclohexane-1,4-dicarboxamide-κ3-O:N:N′)-(p-toluenesulfonato-κ2O,O′)silver(I)], C25H27Ag1N4O5S
  26. The crystal structure of 1,2-bis(3-bromophenoxy) ethane, C14H12Br2O2
  27. The crystal structure of 4-(pyren-1-yl)butyl-3-nitrobenzoate, C27H21NO4
  28. Crystal structure of bis[(2-(4-chlorophenyl)-5-methyl-1,3-dioxane-5-carboxylato-κ1O) (5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II), C40H60Cl2N4NiO8
  29. The crystal structure of 1,5-dinitro-2,3,4-trichlorobenzene, C6H1Cl3N2O4
  30. The crystal structure of the solid solution of 3,5-dinitropyrazole and 4-chlorine-3,5-dinitropyrazole, C3H1.24Cl0.76N4O4
  31. The cocrystal structure of 4-nitropyrazole — acetic acid (1/1), C5H7N3O4
  32. The crystal structure of propan-2-one O-(2,4,6-trinitrophenyl) oxime, C9H8N4O7
  33. The crystal structure of ethyl 2-(3-(2-ethoxy-2-oxoethyl)benzo[d] thiazol-2(3H)-ylidene)acetate, C15H17NO4S
  34. Crystal structure of (acetic acid-κ1O)-bis(μ2-2-chlorobenzoato-κ2O:O′)-(2-chlorobenzoato-κ1O)-(μ2-hydroxy-κ2O:O)-bis(1,10-phenanthroline-κ2N,N′)dimanganese(II) — methanol (1/1), C48H37Cl3Mn2N4O10
  35. Crystal structure of 3-methyl-2-phenyl-1,8-naphthyridine, C15H12N2
  36. Crystal structure of chlorido-(5-acetyl-2-(5-methylpyridin-2-yl)benzen-1-ido-κ2C,N)-pyridine-κN-palladium(II), C19H17ClN2OPd
  37. Crystal structure of (4-methyl-benzoato-κ2O,O′)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, C24H45ClN4NiO7
  38. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6) 1,2,3,4,5-pentamethyl-cyclopenta-2,4-dien-1-yl(potassium, rubidium) — ammonia (1/2), [K0.3Rb0.7(18-crown-6)]Cp*⋅2 NH3, C22H45K0.3N2O6Rb0.7
  39. Crystal structure of (3E,5E)-1-((4-fluorophenyl)sulfonyl)-3,5-bis(3-nitrobenzylidene)piperidin-4-one — dichloromethane (2/1), C51H38Cl2F2N6O14S2
  40. Crystal structure of (E)-N′-((1,6-dihydropyren-1-yl)methylene)isonicotinohydrazide — methanol (1/1), C24H19N3O2
  41. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ3N,O:O′)-(μ4-hexamethylenetetramino-κ4N:N′:N′′:N′′′)disilver(I)] monohydrate, C12H21Ag2N5O8S2
  42. Crystal structure of bis(acridin-10-ium) 2,5-dihydroxyterephthalate — 2,5-dihydroxyterephthalic acid (1/1), C21H15NO6
  43. The crystal structure of 1,12-diazaperylene, C18H10N2
  44. Crystal structure of 1-(5-(4-chlorophenyl)-3-(2-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one, C17H14N2OFCl
  45. Crystal structure of (4aR,6aR,6bR,10S,12aR)-10-acetoxy-1,2,3,4, 4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a, 12b,13,14b-icosahydro-2,2,4a,6b,9,9,12a-heptamethylpicene-6a-carboxylic acid, C32H50O4
  46. The crystal structure of tetrachlorido-bis{1,3-bis(2,6-diisopropylphenyl)-1H-3λ4-imidazol-2-yl}-(μ2-pyrimidine-κ2N:N′)dipalladium(IV) — dichloromethane (1/2), C60H80Cl8N6Pd2
  47. The crystal structure of (E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-yl 4-nitrobenzoate, C22H19NO7
  48. Crystal structure of 3-methyl-N-(pyrimidin-5-ylmethyl)pyridin-2-amine, C11H12N4
  49. The crystal structure of 2,5-dichloroterephthalic acid dihydrate, C8H8Cl2O6
  50. The crystal structure of 2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine — dimethylformamide (1/1), C33H28N10O
  51. Crystal structure of N-(adamantan-1-yl)-5-(dimethylamino)naphthalene-1-sulfonamide, C22H28N2O2S
  52. Crystal structure of poly[diaqua-(μ4-4-(3,5-dicarboxy-κ1O-phenoxy)phthalato-κ3O:O′:O′)cadmium(II)], C16H12CdO11
  53. Crystal structure of poly[diaqua-bis(μ2-3-((1H-imidazol-1-yl)methyl)benzoato-κ2N:O)manganese(II)], C22H22MnN4O6
  54. Crystal structure of 9-(3-phenoxyphenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione, C25H23NO3
  55. The crystal structure of poly[(μ3-2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine-k3N:N′:N′′)-(nitrato-k2O,O)-(nitrato-k1O)zinc(II)] - N,N-dimethylacetamide (1/2), C38H39N13O8Zn
  56. Crystal structure of poly[(μ7-4-(3,5-dicarboxylatophenoxy)phthalato)-(1,10-phenanthroline-κ2N,N′)dizinc(II)], C28H14N2O9Zn2
  57. The crystal structure of methyl 2-(benzylamino)-5-(benzyloxy)benzoate, C22H21NO3
  58. Crystal structure of (1,4,8,11-tetraazacyclotetradecane)palladium(II) tetracyanoplatinate(II), C14H24N8PdPt
  59. Crystal structure of (pyridine-2-carboxylato-κ2N,O)-[2-(2-pyridyl)phenyl-κ2N,C1]palladium(II), C17H12N2O2Pd
  60. Crystal structure of (cyclohexane-1,4-diammonium) 4-[(4-carboxylatophenyl)disulfanyl]benzoate dimethylsulphoxide hydrate (1/1/1/1), [C6H16N2]2+[C14H8O4S2]2−⋅C2H6OS⋅H2O
  61. Crystal structure of the 2:1 co-crystal 2-[(2-carboxyphenyl)disulfanyl]benzoic acid – 3-bromobenzoic acid, 2(C14H10O4S2)⋅C7H5BrO2
  62. Crystal structure of chlorido-dimethyl-(phenylpiperazine-1-carbodithioato-κ2S,S′)tin(IV), C13H19ClN2S2Sn
  63. Crystal structure of (N-n-butyl, N-methyl-dithiocarbamato-κ2 S,S′)-chlorido-dimethyl-tin(IV), C8H18ClNS2Sn
  64. Crystal structure of (2,2′-bipyridyl)bis(4-bromobenzyl)dibromidotin(IV), C24H20Br4N2Sn
  65. Crystal structure of (2,2′-bipyridyl)bis(4-chlorobenzyl)dichloridotin(IV), C24H20Cl4N2Sn
  66. Crystal structure of N-methyl-N-phenyl(methylsulfanyl)carbothioamide, C9H11NS2
  67. Crystal structure of 4-phenylpiperazin-1-ium (4-phenylpiperazin-1-yl)carbothioylsulfanide, [C10H15N2][C11H13N2S2]
  68. Crystal structure of catena-{di-aqua-sodium [n-butyl(methyl)carbamothioyl]sulfanide}n, [C6H16NNaO2S2]n
  69. Crystal structure of (2-([1,1-bis(hydroxymethyl)-2-oxyethyl]iminomethyl)-5-(n-decyl)phenolato)-dimethyl-tin(IV), C23H39NO5Sn
  70. Crystal structure of 4-chloro-N′-[(1E)-(3-ethoxy-2-hydroxyphenyl)methylidene]benzohydrazide – a Z′ = 3 structure, C16H15ClN2O3
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