Startseite Crystal structure of 2-[(1E)-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]iminiumyl}methyl]-5-(dodecyloxy)benzen-1-olate, C23H39NO5
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Crystal structure of 2-[(1E)-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]iminiumyl}methyl]-5-(dodecyloxy)benzen-1-olate, C23H39NO5

  • See Mun Lee , Kong Mun Lo und Edward R.T. Tiekink ORCID logo EMAIL logo
Veröffentlicht/Copyright: 14. Oktober 2019
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 235 Heft 1

Abstract

C23H39NO5, monoclinic, P21/c (no. 14), a = 26.1698(4) Å, b = 9.4863(2) Å, c = 9.0929(2) Å, β = 97.376(2)°, V = 2238.67(8) Å3, Z = 4, Rgt(F) = 0.0539, wRref(F2) = 0.1580, T = 100(2) K.

CCDC no.: 1957130

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:Yellow prism
Size:0.13 × 0.03 × 0.02 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:0.68 mm−1
Diffractometer, scan mode:XtaLAB Synergy, ω
θmax, completeness:67.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:27272, 4004, 0.040
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3452
N(param)refined:275
Programs:CrysAlisPRO [1], SHELX [2], [3], WinGX/ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
O10.89812(5)1.10031(14)0.50569(14)0.0184(3)
H1O0.8900(9)1.055(2)0.4268(18)0.028*
O20.93683(5)1.17452(14)0.86963(15)0.0192(3)
H2O0.9203(9)1.236(2)0.911(3)0.029*
O30.97309(5)0.82780(15)0.93578(15)0.0231(3)
H3O1.0012(6)0.829(3)0.991(3)0.035*
O40.87899(6)0.57144(14)0.78365(15)0.0230(3)
O50.75800(6)0.30758(15)0.45315(16)0.0247(3)
N10.89831(6)0.83173(16)0.70445(17)0.0160(3)
H1N0.9040(9)0.7597(17)0.764(2)0.019*
C10.93071(7)0.95905(19)0.7299(2)0.0146(4)
C20.94145(7)1.0290(2)0.5849(2)0.0172(4)
H2A0.96981.09770.60780.021*
H2B0.95340.95580.51950.021*
C30.90380(7)1.05744(19)0.8288(2)0.0166(4)
H3A0.87081.09080.77470.020*
H3B0.89641.00650.91870.020*
C40.98251(7)0.9067(2)0.8083(2)0.0182(4)
H4A0.99970.84650.74050.022*
H4B1.00530.98780.83850.022*
C50.86144(7)0.8098(2)0.5962(2)0.0170(4)
H50.85210.88540.52960.020*
C60.83438(7)0.6815(2)0.5712(2)0.0172(4)
C70.84556(7)0.5621(2)0.6670(2)0.0174(4)
C80.81897(8)0.4341(2)0.6276(2)0.0195(4)
H80.82530.35350.68920.023*
C90.78412(7)0.4261(2)0.5006(2)0.0189(4)
C100.77303(8)0.5445(2)0.4064(2)0.0212(4)
H100.74870.53750.31970.025*
C110.79790(8)0.6684(2)0.4427(2)0.0204(4)
H110.79060.74800.38010.024*
C120.76677(8)0.1823(2)0.5427(2)0.0238(5)
H12A0.75700.19890.64280.029*
H12B0.80360.15570.55300.029*
C130.73421(9)0.0668(2)0.4658(3)0.0323(5)
H13A0.7410−0.02170.52260.039*
H13B0.74480.05190.36620.039*
C140.67641(9)0.0967(3)0.4485(3)0.0383(6)
H14A0.66970.18400.38940.046*
H14B0.65830.01870.39110.046*
C150.65341(9)0.1135(3)0.5903(3)0.0396(6)
H15A0.66550.03450.65700.048*
H15B0.66680.20180.63880.048*
C160.59630(10)0.1175(4)0.5752(3)0.0480(7)
H16A0.58480.19520.50630.058*
H16B0.58350.02870.52640.058*
C170.57043(11)0.1349(4)0.7065(4)0.0597(9)
H17A0.57980.22950.74740.072*
H17B0.58570.06540.78060.072*
C180.51451(11)0.1220(4)0.6989(3)0.0540(8)
H18A0.49940.19060.62340.065*
H18B0.50540.02710.65850.065*
C190.48748(11)0.1401(5)0.8267(4)0.0707(11)
H19A0.49500.23700.86360.085*
H19B0.50400.07540.90410.085*
C200.43222(10)0.1204(4)0.8214(3)0.0542(8)
H20A0.42440.02450.78200.065*
H20B0.41560.18720.74640.065*
C210.40593(12)0.1355(5)0.9530(4)0.0708(11)
H21A0.41100.23420.98720.085*
H21B0.42450.07511.03110.085*
C220.35122(12)0.1044(5)0.9484(4)0.0739(12)
H22A0.34200.11691.04990.089*
H22B0.34610.00350.92280.089*
C230.31410(12)0.1865(4)0.8462(4)0.0554(8)
H23A0.31460.28510.87840.083*
H23B0.27940.14770.84660.083*
H23C0.32370.18120.74560.083*

Source of material

The melting point of the compound was measured on a Mel-Temp II digital melting point apparatus and was uncorrected. The IR spectrum was recorded using a Perkin-Elmer RX1 spectrophotometer as a Nujol mull in a KBr cell from 4000 to 400 cm−1. The 1H NMR spectrum was recorded in CDCl3 solution on a Jeol JNM-ECA 400 MHz NMR spectrometer with chemical shifts relative to tetramethylsilane.

4-Dodecyloxy-2-hydroxybenzaldehyde was synthesized according to a literature procedure [5]. The prepared aldehyde (0.31 g, 1.0 mmol) was added to an ethanolic solution (10 mL) of tris(hydroxymethyl)aminomethane (Tokyo Chemical Industry, 0.12 g, 1.0 mmol) and refluxed for 3 h. The filtrate was evaporated slowly until a yellow precipitate was formed. The precipitate was recrystallized from methanol-hexane by slow evaporation to yield yellow crystals. Yield: 0.16 g (39.1%). M.pt: 383–384 K. IR (cm−1) 3233 (br) ν(O—H), 1634 (s) ν(C—N), 1525 (s) ν(C—O), 1047 (s) ν(C—O), 1016 (m) ν(C—O). 1H NMR (CDCl3, ppm): δ 0.86 (s, 3H, CH3), 1.24–1.79 (m, 20H, CH2), 3.70–4.00 (m, 8H, OCH2), 6.40 (d, 1H, Ph—H), 6.51 (d, 1H, Ph—H), 7.37 (1H, Ph—H), 8.41 (s, 1H, N= CH); OH and NH protons were not observed.

Experimental details

The C-bound H atoms were geometrically placed (C—H = 0.95–0.99 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). The O- and N-bound H-atoms were located in a difference Fourier map but were refined with distance restraints of O—H = 0.84±0.01 Å and N—H = 0.88±0.01 Å, respectively, and with Uiso(H) set to 1.5Ueq(O) and 1.2Ueq(N), respectively. As evident from the figure, the long chain suffers from typical disorder. Careful modelling did not reveal any chemically useful information and so, the simpler model was retained.

Comment

In connection with recent studies of diorganotin Schiff bases derived from tris[(hydroxymethyl)aminomethane] [6], [7], largely motivated by the promising cytotoxicities they exhibit [6], the structure of the title tris[(hydroxymethyl)aminomethane] Schiff base derivative, featuring an appended n-dodecyl substituent, was prepared and studied crystallographically.

The molecular structure is shown in the figure (50% displacement ellipsoids) and crystallography confirms the molecule existing as a zwitterion in the solid-state. Proton transfer has occurred from the phenol group to the imine-nitrogen atom (see the figure). An intramolecular, charge-assisted medium-strong imine-N—H⋯O(phenoxide) hydrogen bond is evident [N1—H1n⋯O4: H1n⋯O4 = 1.918(17) Å, N1⋯O4 = 2.639(2) Å with angle at H1n = 138.9(19)°]. The C5—N1 imine bond length is 1.303(3) Å and the configuration about this bond is E. The imine residue is co-planar with the phenyl ring to which it is connected with the N1—C5—C6—C11 and N1—C5—C6—C7 torsion angles being −175.12(18) and 0.5(3)°, respectively. The alpha-methylene atom of the n-dodecyl chain is co-planar with the phenyl ring as seen in the values of the C12—O5—C9—C8 and C12—O5—C9—C10 torsion angles of 0.9(3) and −179.71(17)°, respectively. A kink is then evident in the chain with the O5—C12—C13—C14 and C12—C13—C14—C15 torsion angles of −61.5(2) and −61.9(3)°, respectively, being indicative of – syn-clinal conformations. The remaining methylene atoms of the chain have an almost all-trans conformation with the maximum deviation in torsion angles being −169.7(2)°, for C13—C14—C15—C16.

There is a single literature precedent for the structure reported herein, that is, with a methyl rather than a n-dodecyl substituent [8]. This is also zwitterionic and was characterised as a monohydrate.

In the crystal, the O1-hydroxy group forms a charge-assisted hydrogen bond with the phenoxide-O atom [O1—H1o⋯O4i: H1o⋯O4i = 1.766(18) Å, O1⋯O4i = 2.5927(19) Å with angle at H1o = 167.5(18)° for symmetry operation (i) x, 3/2 − y, −1/2 + z] while the other hydroxy groups participate in hydroxy—O—H⋯O(hydroxy) hydrogen bonds [O2—H2o⋯O1ii: H2o⋯O1ii = 1.90(2) Å, O2⋯O1ii = 2.7279(19) Å with angle at H2o = 166(2)° and O3—H3o⋯O2iii: H3o⋯O2iii = 1.93(2) Å, O3⋯O2iii = 2.7600(19) Å with angle at H3o = 176(3)° for (ii) x, 5/2 − y, 1/2 + z and (iii) 2 − x, 2 − y, 2 − z]. The molecules assemble head-to-head to form a bi-layer, in the bc-plane, sustained by the aforementioned hydrogen bonding interactions. This allows for the inter-digitation of the n-dodecyl chains.

Using established procedures [9] and Crystal Explorer 17 [10], the calculated Hirshfeld surfaces were analysed as were the full and delineated two-dimensional fingerprint plots. The presence of multiple conventional hydrogen bonding interactions is reflected in a significant contribution of H⋯O/O⋯H contacts, that is, 15.4% to the overall surface. This notwithstanding, by far the greatest contribution is made by H⋯H contacts, at 72.9%, reflecting the hydrophobic interactions in the inter-layer region. The only other contribution to the surface contacts of note are from H⋯C/C⋯H contacts of 10.9%, which arise largely from methylene-C3—H⋯π(phenyl) and methyl-C23—H⋯π(phenyl) interactions within the bi-layer constructed from the O—H⋯O hydrogen bonding.

Acknowledgements

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

References

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Received: 2019-07-22
Accepted: 2019-10-02
Published Online: 2019-10-14
Published in Print: 2019-12-18

©2019 See Mun Lee et al., published by De Gruyter, Berlin/Boston

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

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  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-2019-0523
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Artikel in diesem Heft

  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
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