Home Crystal structure of 2,2′-diamino-[1,1′-biphenyl]-4,4′-dicarboxylic acid dihydrate, C14H16N2O6
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Crystal structure of 2,2′-diamino-[1,1′-biphenyl]-4,4′-dicarboxylic acid dihydrate, C14H16N2O6

  • Alla Dikhtiarenko EMAIL logo , Alma I. Olivos Suarez , Alexey Pustovarenko , Santiago García-Granda and Jorge Gascon
Published/Copyright: February 9, 2016

Abstract

C14H16N2O6, triclinic, P1̅ (no. 2), a = 10.0254(5) Å, b = 11.2726(6) Å, c = 13.4494(7) Å, α = 111.535(2)°, β = 92.068(2)°, γ = 102.644(2)°, V = 1368.16(13) Å3, Z = 4, Rgt(F) = 0.047, wRref(F2) = 0.133, T = 150 K.

CCDC no.:: 1038346

The crystal structure is shown in the figure. Tables 13 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Table 1

Data collection and handling.

Crystal:Yellow, tetrahedral, size 0.10×0.20×0.30 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.18 cm−1
Diffractometer, scan mode:Xcalibur, Ruby, Gemini, ω scans
2θmax:61.2°
N(hkl)measured, N(hkl)unique:73950, 8404
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 6147
N(param)refined:477
Programs:XABS2 [6], CrysAlis [7], SIR92 [8], SHELX [9], Diamond [10], WinGX [11], enCIFer [12]
Table 2

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

AtomSitexyzUiso
H(1A)2i0.590(2)0.196(2)−0.103(2)0.025(4)
H(1B)2i0.671(2)0.235(2)0.006(2)0.031(5)
H(2A)2i0.429(2)0.097(2)0.074(1)0.048(6)
H(2B)2i0.393(2)0.067(3)0.165(2)0.062(7)
H(2C)2i0.496(2)0.003(2)0.094(2)0.037(5)
H(3A)2i0.962(2)0.307(2)0.544(2)0.055(7)
H(3)2i0.40300.2839−0.12130.019
H(4)2i0.27690.51900.14310.022
H(6)2i0.42550.47140.24980.022
H(10)2i0.71310.50280.28050.021
H(11)2i0.64500.07700.26760.021
H(12)2i0.85190.45820.39590.020
H(3B)2i0.748(2)1.005(2)0.727(2)0.034(5)
H(3C)2i0.842(2)1.051(2)0.829(2)0.034(5)
H(4A)2i0.859(2)1.023(2)0.525(2)0.048(6)
H(4B)2i0.897(2)0.956(2)0.595(2)0.040(6)
H(5)2i1.074(2)0.559(2)0.893(2)0.050(6)
H(8)2i0.214(3)0.739(2)0.264(2)0.055(7)
H(17)2i0.88590.53070.67210.022
H(18)2i0.94680.90600.88090.022
H(20)2i0.74950.57230.55330.021
H(23)2i0.50500.63790.56540.022
H(25)2i0.64600.94340.41210.024
H(26)2i0.35360.65510.44130.023
H(9WA)2i0.030(3)0.700(2)0.157(2)0.045(6)
H(9WB)2i0.136(2)0.660(2)0.099(2)0.050(7)
H(10A)2i0.096(3)0.306(3)0.687(2)0.056(7)
H(10B)2i0.101(3)0.199(3)0.584(2)0.080(9)
H(11A)2i0.158(3)0.166(3)0.805(2)0.074(8)
H(11B)2i0.144(3)0.023(3)0.732(2)0.074(8)
H(12A)2i0.231(3)0.057(3)0.910(2)0.067(8)
H(12B)2i0.215(3)−0.059(3)0.950(2)0.078(9)
Table 3

Atomic displacement parameters (Å2).

AtomSitexyzU11U22U33U12U13U23
C(1)2i0.2193(1)0.4262(1)−0.0703(1)0.0149(6)0.0169(6)0.0217(6)0.0029(5)−0.0032(5)0.0101(5)
C(2)2i0.3226(1)0.4029(1)−0.0002(1)0.0138(6)0.0151(6)0.0201(6)0.0029(4)−0.0023(5)0.0093(5)
C(3)2i0.4079(1)0.3212(1)−0.0467(1)0.0158(6)0.0164(6)0.0153(6)0.0029(5)−0.0023(5)0.0075(5)
C(4)2i0.3311(1)0.4615(1)0.1116(1)0.0189(6)0.0197(6)0.0207(6)0.0099(5)0.0011(5)0.0088(5)
C(5)2i0.5007(1)0.2943(1)0.0171(1)0.0133(6)0.0144(6)0.0190(6)0.0040(4)0.0004(5)0.0078(5)
C(6)2i0.4208(1)0.4332(1)0.1752(1)0.0208(6)0.0212(6)0.0162(6)0.0090(5)0.0003(5)0.0080(5)
C(7)2i0.5043(1)0.3484(1)0.1298(1)0.0140(6)0.0168(6)0.0187(6)0.0044(5)−0.0014(5)0.0092(5)
C(8)2i0.5947(1)0.3172(1)0.2022(1)0.0154(6)0.0189(6)0.0150(6)0.0077(5)0.0015(5)0.0085(5)
C(9)2i0.5761(1)0.1902(1)0.2014(1)0.0153(6)0.0170(6)0.0163(6)0.0053(5)−0.0008(5)0.0066(5)
C(10)2i0.6993(1)0.4170(1)0.2772(1)0.0177(6)0.0173(6)0.0194(6)0.0054(5)0.0011(5)0.0099(5)
C(11)2i0.6589(1)0.1625(1)0.2702(1)0.0183(6)0.0171(6)0.0201(6)0.0062(5)−0.0006(5)0.0099(5)
C(12)2i0.7827(1)0.3906(1)0.3467(1)0.0145(6)0.0189(6)0.0170(6)0.0038(5)0.0003(5)0.0080(5)
C(13)2i0.7629(1)0.2628(1)0.3430(1)0.0158(6)0.0199(6)0.0158(6)0.0070(5)0.0014(5)0.0093(5)
C(14)2i0.8490(1)0.2311(1)0.4178(1)0.0149(6)0.0201(6)0.0178(6)0.0038(5)−0.0012(5)0.0095(5)
N(1)2i0.5840(1)0.2086(1)−0.0317(1)0.0163(5)0.0205(5)0.0175(5)0.0079(4)0.0004(4)0.0074(4)
N(2)2i0.4649(1)0.0831(1)0.1298(1)0.0209(6)0.0189(6)0.0195(6)0.0060(5)−0.0025(5)0.0069(5)
O(1)2i0.1756(1)0.5284(1)−0.03006(8)0.0232(5)0.0212(5)0.0246(5)0.0116(4)−0.0032(4)0.0096(4)
O(2)2i0.1790(1)0.3419(1)−0.16484(8)0.0278(6)0.0214(5)0.0226(5)0.0073(4)−0.0110(4)0.0064(4)
O(3)2i0.9150(1)0.3343(1)0.50236(8)0.0232(5)0.0220(5)0.0185(5)0.0052(4)−0.0055(4)0.0083(4)
O(4)2i0.8550(1)0.1185(1)0.40230(9)0.0317(6)0.0203(5)0.0262(5)0.0079(4)−0.0085(4)0.0106(4)
C(15)2i1.0277(1)0.6921(1)0.8622(1)0.0151(6)0.0208(6)0.0230(6)0.0057(5)0.0001(5)0.0123(5)
C(16)2i0.9326(1)0.7156(1)0.7874(1)0.0134(6)0.0203(6)0.0212(6)0.0050(5)0.0007(5)0.0127(5)
C(17)2i0.8712(1)0.6143(1)0.6897(1)0.0172(6)0.0173(6)0.0227(6)0.0073(5)0.0010(5)0.0097(5)
C(18)2i0.9061(1)0.8389(1)0.8153(1)0.0175(6)0.0178(6)0.0195(6)0.0039(5)−0.0026(5)0.0074(5)
C(19)2i0.8187(1)0.8627(1)0.7458(1)0.0152(6)0.0165(6)0.0214(6)0.0052(5)0.0003(5)0.0089(5)
C(20)2i0.7883(1)0.6393(1)0.6194(1)0.0178(6)0.0183(6)0.0175(6)0.0052(5)−0.0006(5)0.0074(5)
C(21)2i0.7610(1)0.7631(1)0.6451(1)0.0126(6)0.0184(6)0.0199(6)0.0043(5)0.0002(5)0.0112(5)
C(22)2i0.6671(1)0.7813(1)0.5667(1)0.0158(6)0.0179(6)0.0174(6)0.0054(5)0.0002(5)0.0087(5)
C(23)2i0.5334(1)0.7000(1)0.5353(1)0.0173(6)0.0206(6)0.0187(6)0.0033(5)0.0007(5)0.0115(5)
C(24)2i0.7107(1)0.8727(1)0.5181(1)0.0141(6)0.0206(6)0.0233(7)0.0042(5)−0.0006(5)0.0125(5)
C(25)2i0.6184(1)0.8822(1)0.4432(1)0.0177(6)0.0227(7)0.0238(7)0.0050(5)0.0006(5)0.0148(5)
C(26)2i0.4425(1)0.7095(1)0.4606(1)0.0148(6)0.0224(6)0.0194(6)0.0030(5)−0.0009(5)0.0094(5)
C(27)2i0.4855(1)0.8014(1)0.4144(1)0.0171(6)0.0209(6)0.0174(6)0.0072(5)0.0007(5)0.0084(5)
C(28)2i0.3918(1)0.8121(1)0.3318(1)0.0190(6)0.0219(6)0.0183(6)0.0068(5)−0.0005(5)0.0078(5)
N(3)2i0.7786(1)0.9830(1)0.7817(1)0.0254(6)0.0167(6)0.0265(6)0.0075(5)−0.0034(5)0.0083(5)
N(4)2i0.8477(1)0.9447(1)0.5355(1)0.0167(6)0.0316(7)0.0413(8)−0.0015(5)−0.0063(5)0.0262(6)
O(5)2i1.0122(1)0.5671(1)0.84319(9)0.0216(5)0.0209(5)0.0305(6)0.0058(4)−0.0056(4)0.0146(4)
O(6)2i1.1121(1)0.7807(1)0.93305(9)0.0271(6)0.0242(5)0.0327(6)0.0030(4)−0.0117(4)0.0137(5)
O(7)2i0.4297(1)0.8765(1)0.27761(9)0.0269(6)0.0334(6)0.0272(6)0.0043(5)−0.0048(4)0.0192(5)
O(8)2i0.2642(1)0.7431(1)0.32201(9)0.0173(5)0.0431(7)0.0295(6)0.0023(5)−0.0064(4)0.0221(5)
O(9W)2i0.1158(1)0.7216(1)0.15266(9)0.0208(5)0.0237(5)0.0226(5)0.0036(4)−0.0052(4)0.0074(4)
O(10W)2i0.0556(1)0.2622(2)0.6247(1)0.0436(8)0.0531(8)0.0213(6)0.0257(7)−0.0073(5)0.0108(6)
O(11W)2i0.1301(2)0.0794(1)0.8041(1)0.0516(8)0.0234(6)0.0401(7)0.0066(6)−0.0029(6)0.0117(5)
O(12W)2i0.2773(1)0.0250(1)0.9551(1)0.0352(6)0.0238(6)0.0328(6)−0.0002(5)−0.0120(5)0.0109(5)

Source of material

2,2′-Dinitrophenyl-4,4′-dicarboxylic acid dimethyl ester was reduced in an ethanolic solution with 5.8 g of SnCl2 · H2O and 3 mL of concentrated HCl. After partial evaporation of the solvent, the 2,2′-diamino-[1,1′-biphenyl]-4,4′-dicarboxylic acid dimethyl ester was recrystallized from hexane. The final product was obtained after deprotection of the ester with KOH in THF. Yielding (56%) a light-yellow solid. Crystals for X-ray diffraction measurements were grown in TMOS gel media containing 0.37 mmol of 2,2′-diamino-[1,1′-biphenyl]-4,4′-dicarboxylic acid, which previously has been neutralized with LiOH, and under-layered with 0.01M HCl. Yellow rectangular shaped crystals of title compound were formed in the gel phase after two weeks.

Experimental details

Hydrogen atoms belonging to carboxylic, amino- groups and water molecules were taken from a ΔF map. All aromatic and methyl hydrogen atoms were placed in calculated position and then refined with riding model with C—H lengths of 0.93 Å and 0.96 Å (Uiso(H) = 1.2Ueq(C) for aromatic and Uiso(H) = 1.5Ueq(C) for methyl), respectively.

Discussion

In recent years, research on coordination polymers and metal-organic frameworks has made considerable progress. These microporous crystalline materials exhibit intriguing properties, such as molecular adsorption, magnetism and luminescence [1, 2]. Non-covalent intermolecular interactions, mainly hydrogen bonding and aromatic interactions of aromatic carboxylates play a key role in the crystal packing of such coordination polymers [3, 4]. Although carboxylic linkers are most commonly used to build up metal-organic frameworks [5], the crystal structures of these carboxylic acids are rarely reported. Recently, we crystallize the title compound using TMOS gel media.

The asymmetric unit of the title compound (Figure) contains two 2,2′-diamino-[1,1′-biphenyl]-4,4′-dicarboxylic acid and four water molecules. One of the two independent acid molecules is found to be in its zwitterionic form (COO/NH3+) whereas the other is neutral. Due to steric hindrance, in both carboxylic acid molecules, the planes of the aromatic rings in the biphenyl moiety are twisted with respect to each other with a dihedral angle of 63.4° and 60.1° respectively. Notably, the larger angle of repulsion is attributed to the protonation of the amino-group (–NH3+) in one of the carboxylic acid molecules. The cis-conformation of 2,2′-diamino-[1,1′-biphenyl]-4,4′-dicarboxylic acid molecules is established by the weak N2–H2a·N1 and N3–H3b·N4 intramolecular contact with the distance of 3.138(2) Å and 3.299(2) Å. Herein, the planes of all the carboxylic groups are slightly deviated from the planes of the neighbouring aromatic rings and show a dihedral angle of 9.7°, 20.3°, 17.8° and 23.6° for O8–C28–O7, O5–C15–O6, O3–C14–O4 and O1–C1–O2 groups, respectively. The C=O bond lengths of the carboxylic groups C14–O4, C15–O6 and C28–O7 are 1.2236(17) Å, 1.2228(17) Å and 1.2216(17) Å, respectively. The bond lengths of 1.3123(16) Å, 1.3085(17) Å, 1.3170(18) Å for C14–O3, C15–O5 and C28–O8 are as expected. In the O1–C1–O2 carboxylic group the O1–C1 and O2–C1 bond length are nearly equal (1.261 Å and 1.263 Å, respectively), indicating that the double bond in the O1–C1–O2 carboxylic group is delocalized, as a result of deprotonation.

In the crystal, two 2,2′-diamino-[1,1′-biphenyl]-4,4′-dicarboxylic acid and four water molecules are linked by intermolecular O–H⋯N, O–H⋯O and N–H⋯N hydrogen bonds. Two co-planar acid molecules are linked via O5–H5⋯O1 to form a dimer moiety that extends through multiple hydrogen bonds involving the carboxylate, the amino groups and water molecules into a 3D hydrogen bonded framework.


Corresponding author: Alla Dikhtiarenko, Catalysis Engineering, Department of Chemical Engineering, Faculty of Applied Sciences, Delft University of Technology, Julianalaan 136, Delft 2628BL, The Netherlands, e-mail:

Acknowledgements:

The research leading to these results has received funding from the European Research Council under the European Union's Seventh Framework Programme (FP/2007–2013) / ERC Grant Agreement No.335746, CrystEng-MOF-MMM. S. G.-G. thanks to Ministerio de Economía y Competitividad, MAT2013-40950-R, for financial support.

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Received: 2015-11-19
Accepted: 2016-1-18
Published Online: 2016-2-9
Published in Print: 2016-3-1

©2016 Alla Dikhtiarenko et al., published by De Gruyter.

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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  26. Crystal structure of 2,4-dichlorobenzene anhydride, C14H6Cl4O3
  27. Crystal structure of bis(2-hydroxy-2-phenylacetato-κ2O,O′)bis(pyridine-κN)nickel(II), C26H24N2NiO6
  28. Crystal structure of (E)-4-nitro-2-(((3-(tetrahydro-8λ4-[1,3,2]oxazaborolo[2,3-b][1,3,2]oxaborol-8-yl)phenyl)imino)methyl)phenol – water (1/2), C17H18BN3O5·2H2O
  29. Crystal structure of 5-(4-carboxyphenoxy)-nicotinic acid, C13H9NO5
  30. Crystal structure of catena-poly[hexaaquabis(μ2-3-nitrophthalate-κ2O:O′)-(μ2-1,4-bis(4-pyridylmethyl)piperazine-κ2N:N′)dimanganese(II)] dihydrate, C32H42Mn2N6O20
  31. Crystal structure of diaquabis(bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate-κ4O, O′:/O′′,O′′′)bis-(2,2′-bipyridine-κ2N, N′)dicadmium(II) hydrate
  32. Crystal structure of (R)-1-(1-(6-fluorobenzo[d]thiazol-2-yl)ethyl)-3-phenylthiourea
  33. Crystal structure of poly[(μ2-1,4-bis((1H-imidiazol-1-yl)methyl)benzene-κ2N:N′)-(μ2-4,4′-(1,2-phenylenebis(oxy)dibenzoato-κ4O,O′:O′′,O′′′)nickel(II)], C34H26O6N4Ni
  34. Crystal structure of 3′,4′,5-trihydroxy-3,7-dimethoxyflavone, C17H14O7
  35. Crystal structure of n-butyl-chlorido-bis[N-sec-butyl,N-n-propyl-carbamodithioato κ2S,S′]-tin(IV), C20H41ClN2S4Sn
  36. Crystal structure of poly[bis(μ4-4,4′-(1,2-phenylenebis(oxy))dibenzoato-κ4O:O′:O′′:O′′′)bis(μ3-4,4′-(1,2-phenylenebis(oxy))dibenzoato–κ3O:O′:O′′)(μ2-1-(4-((1H-imidazol-1-yl)methyl)benzyl)-1H-imidazole-κ2N:N′)tetracobalt(II)], C94H62O24N4Co4
  37. Crystal structure of catenapoly[diaqua-(μ24,4′-bipyridine)-κ2N:N′)-bis(2,6-difluorobenzoate)-κO)nickel(II)] ethanol monosolvate, C28H30F4N2O8Ni
  38. Crystal structure of 2-(9H-fluoren-9-ylidene)hydrazine-1-carbothioamide, C14H11N3S
  39. Crystal structure of 2-(4-methoxyphenyl)-2,3-dihydro-1H-perimidine, C18H16N2O
  40. Crystal structure of catena-poly[diaquabis(μ2-3-carboxybenzene-1,2-dicarboxylato-1:2κ2O:O′)-(μ2-1,4-bis(2-ethylbenzimidazol-1-ylmethyl)-benzene-1:1′κ2N:N′)dizinc(II)], [Zn2(C26H26N4)(C9H4O6)2(H2O)2]
  41. Crystal structure of diaquabis(phenoxyacetato-κ2O,O′)-zinc(II), C16H18O8Zn
  42. Crystal structure of 4-(1H-imidazol-1-yl)-6-pyrimidinylferrocene, C17H14FeN4
  43. Crystal structure of [2-(4-methoxyphenyl)pyrazine-κ2C,N) chlorido[N,N′-bis-(2,6-diisopropyl-phenyl)imidazol-2-ylidene-κC)] palladium(II), C38H45ClN4OPd
  44. Crystal structure of 2-(4-acetyl-2,6-dimethyl-phenyl)-5,6-dichloro-isoindole-1,3-dione, C18H13Cl2NO3
  45. Crystal structure of 4,4′-bipyridin-1-ium 3,3′,5′-tricarboxy-[1,1′-biphenyl]-2-carboxylate, (C26H18N2O8)
  46. Crystal structure of catena-poly[diaqua-μ2-4,4′-biphenyl-4,4′-diyldipyridine-κ2N:N′-bis(5-carboxy-2,6-dimethylpyridine-3-carboxylato-κO)nickel(II)] dihydrate, C40H40N4O12Ni
  47. Crystal structure of poly-[μ2-4,4′-bipyridine-κ2N:N′−μ3-thiophene-2,3-di-carboxylato-κ4O,O′, O′′:O′′′ -cadmium(II)]
  48. Crystal structure of hexaaquamanganese(II) bis(3-carboxythiophene-2-carboxylate) C12H18MnO14S2
  49. Crystal structure of 4-(3-(pyridin-3-yl)-1H-1,2,4-triazol-5-yl)benzoic acid, C14H10N4O2
  50. Crystal structure of (E)-2-(benzo[d]thiazol-2-yl)-3-(pyridin-3-yl)acrylonitrile)
  51. Crystal structure of catena-poly[2,2′-bipyridinyl-6,6′-dicarboxylato-κ4N,N′,O,O′)-(μ2-2,2′-bipyridinyl-6′-carboxyl-6-carboxylato-κ5N,N′,O,O′:O′′)samarium(III)] monohydrate, C24H13N4O8Sm · H2O
  52. Crystal structure of catena-poly[bis(μ2-4-(3-(pyridin-3-yl)-1H-1,2,4-triazol-5-yl)benzoato)-κ2N:O)copper(II)] dihydrate, C28H22N8O6Cu
  53. Crystal structure of catena-poly[tetraaqua-(μ2-4,4′-bipyridine-k2N:N′)-zinc(II)] fumarate tetrahydrate, C14H26N2O12Zn
  54. Crystal structure of triaqua-(1,10-phenanthroline)-(dihydrogen-3,3′,3′′-(2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tripropanoato) cobalt(II)dihydrogen-3,3′,3′′-(2,4,6-trioxo-1,3,5-triazinane-1,3,5-triyl)tripropanoate, C72H82Co2N16O42
  55. Crystal structure of poly[dibromido-(μ2–4,4′-bis-(pyrid-4-yl)biphenyl-κ2N:N′)lead(II)], C22H16N2PbBr2
  56. Crystal structure of catena-poly[diaqua-bis(μ2-5-carboxy-2-(pyridin-4-yl)benzoato-κ2O:N)-cobalt(II)]dihydrate, C26H24N2O12Co
  57. Crystal structure of 5-(4-pyridyl)pyrimidine–4,4′-bipyridine–1,3,5-benzenetriol–water (1:1:1:1), C25H23N5O4
  58. Crystal structure of 5-hydroxy-4-((4-hydroxyphenyl)imino)naphthalen-1(4H)-one monohydrate, C16H11NO3 · 0.5H2O
  59. Crystal structure of 2-amino-N-(4-methoxyphenyl)benzamide, C14H14N2O2
  60. Crystal structure of (2,5-dihydroxyphenyl)-(4-hydroxy-3,5-dimethoxyphenyl)methanone, C15H14O6
  61. Crystal structure of dichlorido[bis(2-hydroxyethyl)5′-([2,2′:6′,2′′-terpyridin]-4′-yl)-[1,1′:3′,1′′-terphenyl]-4,4′′-dicarboxylato]zinc(II), C39H31Cl2N3O6Zn
  62. Crystal structure of bis[4-(3-carboxy-6-fluoro-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium] benzene-1,4-dicarboxylate (C20H18F2N3O3)2(C8H4O4), C48H40F4N6O10
  63. Crystal structure of (2,5-dihydroxyphenyl)-(4-methoxyphenyl)methanone, C14H12O4
  64. Crystal structure of photochromic 1-(2-methyl-5-phenyl-3-thienyl-2-[2-methyl-5-(4-ethoxylphenyl)-3-thienyl] 3,3,4,4,5,5-hexafluoro-cyclopent-1-ene, C29H22F6OS2
  65. Crystal structure of poly[diaquabis(μ2-biphenyl-2,4′-dicarboxylato-κ2O:O′)tris(μ2-1,1′-biphenyl-4,4′-diylbis(1H-imidazole)-κ2N:N′)dicobalt(II)] monohydrat, C82H64N12O11Co2
  66. Crystal structure of 2-amino-4-(3,4-difluorophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile, C16H12N2O2F2
  67. Crystal structure of poly[(di-μ2-aqua-κ2O:O)bis(μ5-oxalato-1:2κ2O1; 1κ1O2; 3:4:5κ3O3; 3κ1O4)(μ4-oxalato-1:2κ2O1; 2:3κ2O2; 3:4κ2O3; 4:1κ2O4)dizinc(II)disodium(I)]
  68. Crystal structure of tetraethylammonium hexachloridotantalate(V), C8H20Cl6NTa
  69. Crystal structure of (E)-2,4-dibromo-6-(((2-nitrophenyl)imino)methyl)phenol, C13H8Br2N2O3
  70. The crystal structure of 6-chloro-2,4-diphenylquinoline
  71. Crystal structure of (E)-2-(((1,10-phenanthrolin-5-yl)imino)methyl)-5-methylphenol monohydrate, C20H15N3O·H2O
  72. Crystal structure of tris(3-(2-pyridyl)pyrazole)zinc(II)tetrachlorido zincate(II), C24H21Cl4N9Zn2
  73. Crystal structure of 4-chloro-N,N-diethyl-6-(piperidin-1-yl)-1,3,5-triazin-2-amine, C12H20ClN5
  74. The crystal structure of 4-allyl-5-benzyl-2,4-dihydro-3H-1,2,4-triazol-3-one, C12H13N3O
  75. Crystal structure of diethyl 2-(((2-(pyridin-3-ylthio)phenyl)amino)methylene)malonate, C19H20N2O4S
  76. Crystal structure of fac-tricarbonyl(2-(isopropylimino)methyl-5-methylphenolatido-κ2N,O)(pyridine-κN)rhenium(I), C19H19N2O4Re
  77. Crystal structure of 1,3,6,8-tetrakis(p-tolylthio)pyrene, C44H34S4
  78. Crystal structure of catena-poly-(diaqua-(μ2-1,2-bis(4-pyridyl)ethene-κ2N:N′)-(4-methylphthalato-κ2O,O′)-cobalt(II)trihydrate, C21H26CoN2O9
  79. Crystal structure of tetraethylammonium fac-tricarbonyl(hexafluoroacetylacetonato-κ2O,O′)-(nitrato-κO)rhenium(I), C16H21O8N2F6Re
  80. Crystal structure of 3-(thiophen-2-yl)-5-(p-tolyl)-4,5-dihydro-1H-pyrazole-1-carboxamide
  81. Crystal structure of bis(1-ethyl-3-methylimidazolium) tetrabromidocadmate(II), [C6H11N2]2[CdBr4]
  82. Crystal structure of N′-(adamantan-2-ylidene)-isonicotinohydrazide, C16H19N3O
  83. Crystal structure of trans-tetraaquabis(4-(pyridin-4-ylsulfonyl)pyridine-κN)cobalt(II) diperchlorate dihydrate, C20H28Cl2CoN4O18S2
  84. Crystal structure of (Z)-4-(furan-2-yl(p-tolylamino)methylene)-3-methyl-1-p-tolyl-1H-pyrazol-5(4H)-one, C23H21N3O2
  85. Crystal structure of 2-[(4-fluorobenzyl)sulfanyl]-4-(2-methylpropyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile, C16H16FN3OS
  86. Crystal structure of poly[octaaqua-tris(benzene-1,2,4,5-tetracarboxylato)tetralanthanum(III)] hexahydrate, C30H34La4O38
  87. Crystal structure of trans-tetraaqua-bis(4,4′-sulfonyldipyridine-κN)zinc(II) diperchlorate dihydrate, C20H28Cl2ZnN4O18S2
  88. Crystal structure of 4-nitro-thiophene-2-carboxylic acid, a structure with a Z′ = 4, C5H3NO4S
  89. Crystal structure of dirubidium trimercury(II) tetraselenide, Rb2Hg3Se4
  90. Crystal structure of 5-(adamantan-1-yl)-3-[(4-chloroanilino)methyl]-2,3-dihydro-1,3,4-oxadiazole-2-thione, C19H22ClN3OS
  91. Crystal structure of hexaaquamagnesium(II) 5,5′-bitetrazole-1,1′-diolate, C2H12N8O8Mg
  92. The crystal structure of catena-poly[(μ2-1,1′-benzene-1,4-diylbis(1H-benzimidazole-κ2N:N′)silver(I)] nitrate, C20H14N5AgO3
  93. The crystal structure of 1-(2-(4-chlorophenoxy)-4-chlorophenyl)ethanone, C14H10Cl2O2
  94. The crystal structure of 3,5-dinitro-1,3,5-oxadiazinane, C3H6N4O5
  95. Crystal structure of methyl 5-methoxy 1H-indole-2-carboxylate, C11H11NO3
  96. Crystal structure of (Z)-1-(((3-acetyl-2-hydroxyphenyl)amino)methylene)naphthalen-2(1H)-one, C19H15NO3
  97. Crystal structure of (Z)-5-(4-chlorobenzylidene)-2-thioxothiazolidin-4-one —dimethylsulfoxide (1:1), C12H12ClNO2S3
  98. Crystal structure of 5,5′-((4-(trifluoromethyl)phenyl)methylene)bis(1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione) – diethylamine – dichloromethane (1/1/1) C25H32Cl2F3N5O6
  99. Crystal structure of 2-(dimethylsulfanylidene)-N-(4-methoxyphenyl)-3-oxo-3-phenylpropanamide
  100. Crystal structure of (1,10-phenanthroline-κ2N,N′)bis(thiocyanato-κN)platinum(II), C14H8N4PtS2
  101. Crystal structure of di(μ2-chlorido)bis[2-(2-pyridyl)phenyl-κ2N,C1]dipalladium(II), C22H16Cl2N2Pd2
  102. Crystal structure of trans-dibromidodi(pyridine-κN)palladium(II), PdBr2(C5H5N)2
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