Home Crystal structure of bis{N-methyl-N′-[3-(4-methoxyphenyl)-1-methylpropane-1-ylidene]carbamohydrazonothioato}zinc(II), C26H36N6O2S2Zn
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Crystal structure of bis{N-methyl-N′-[3-(4-methoxyphenyl)-1-methylpropane-1-ylidene]carbamohydrazonothioato}zinc(II), C26H36N6O2S2Zn

  • Ming Yueh Tan , Huey Chong Kwong , Karen A. Crouse , Thahira B.S.A. Ravoof and Edward R.T. Tiekink ORCID logo EMAIL logo
Published/Copyright: August 21, 2020
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 235 Issue 6

Abstract

C26H36N6O2S2Zn, triclinic, P1̄ (no. 2), a = 9.1777(5) Å, b = 12.3828(7) Å, c = 13.3137(7) Å, α = 102.157(5)°, β = 101.395(4)°, γ = 100.771(4)°, V = 1408.14(14) Å3, Z = 2, Rgt(F) = 0.0489, wRref(F2) = 0.1147, T = 100(2) K.

CCDC no.: 2023116

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:Colourless slab
Size:0.16 × 0.12 × 0.04 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.06 mm−1
Diffractometer, scan mode:Oxford Diffraction SuperNova, ω
θmax, completeness:28.8°, >99%
N(hkl)measured, N(hkl)unique, Rint:12413, 6335, 0.041
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4742
N(param)refined:346
Programs:CrysAlisPRO [1], SHELX [2], [3], WinGX/ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
Zn0.91082(4)0.22680(3)0.25162(3)0.02339(11)
S11.05901(9)0.21312(8)0.40419(6)0.0312(2)
S20.95685(9)0.17416(7)0.08882(6)0.02683(19)
O10.2828(2)0.17380(17)−0.33342(15)0.0252(5)
O20.7703(2)0.47250(17)0.85343(15)0.0241(5)
N10.9344(3)0.1265(2)0.54031(19)0.0246(6)
H1N1.0282(17)0.134(3)0.576(2)0.030*
N20.7560(3)0.12345(19)0.39549(18)0.0200(5)
N30.7260(3)0.14303(19)0.29480(18)0.0198(5)
N40.8974(3)0.2964(2)−0.05031(19)0.0239(6)
H4N0.871(3)0.3557(17)−0.068(2)0.029*
N50.8602(3)0.37436(19)0.10833(17)0.0189(5)
N60.8690(3)0.3710(2)0.21359(17)0.0184(5)
C10.9009(3)0.1484(2)0.4448(2)0.0226(6)
C20.8186(4)0.0648(3)0.5811(2)0.0284(7)
H2A0.7490310.1127870.5992450.043*
H2B0.8679980.0448310.6445540.043*
H2C0.760462−0.0046870.5269300.043*
C30.5837(3)0.1119(2)0.2430(2)0.0222(6)
C40.4595(4)0.0630(3)0.2906(3)0.0347(8)
H4A0.472653−0.0105550.3020920.052*
H4B0.3594740.0524620.2422170.052*
H4C0.4652670.1152130.3585130.052*
C50.5419(3)0.1171(2)0.1300(2)0.0223(6)
H5A0.4841330.0405200.0859440.027*
H5B0.6373420.1365050.1068050.027*
C60.4458(3)0.2031(3)0.1083(2)0.0253(7)
H6A0.3516070.1864030.1335020.030*
H6B0.5050160.2808210.1483960.030*
C70.4030(3)0.1981(2)−0.0083(2)0.0225(6)
C80.2708(3)0.1227(3)−0.0763(2)0.0257(7)
H80.2043480.075593−0.0480870.031*
C90.2344(3)0.1153(2)−0.1840(2)0.0245(7)
H90.1438640.063324−0.2287770.029*
C100.3300(3)0.1836(2)−0.2266(2)0.0207(6)
C110.4633(3)0.2585(2)−0.1605(2)0.0235(6)
H110.5303620.304856−0.1888900.028*
C120.4976(3)0.2648(3)−0.0531(2)0.0250(7)
H120.5885410.316373−0.0084670.030*
C130.3930(4)0.2258(3)−0.3822(2)0.0291(7)
H13A0.4196440.308402−0.3528190.044*
H13B0.3496750.207772−0.4588990.044*
H13C0.4852390.196625−0.3683830.044*
C140.8999(3)0.2903(2)0.0509(2)0.0201(6)
C150.9007(4)0.2041(3)−0.1360(2)0.0348(8)
H15A0.9386010.145388−0.1068820.052*
H15B0.9686230.232906−0.1777100.052*
H15C0.7971690.171425−0.1816650.052*
C160.8408(3)0.4583(2)0.2724(2)0.0201(6)
C170.8037(4)0.5563(3)0.2320(2)0.0280(7)
H17A0.8755400.5789810.1904410.042*
H17B0.8121100.6204180.2920060.042*
H17C0.6990460.5337050.1870450.042*
C180.8486(3)0.4620(3)0.3864(2)0.0213(6)
H18A0.9170210.5351770.4308150.026*
H18B0.8948790.4002370.4043050.026*
C190.6920(3)0.4494(3)0.4144(2)0.0236(6)
H19A0.6436990.5097770.3951460.028*
H19B0.6242220.3749430.3725790.028*
C200.7088(3)0.4578(2)0.5309(2)0.0212(6)
C210.7537(3)0.3734(3)0.5749(2)0.0258(7)
H210.7707340.3087090.5301420.031*
C220.7742(3)0.3810(3)0.6817(2)0.0255(7)
H220.8053310.3219990.7095040.031*
C230.7495(3)0.4744(2)0.7491(2)0.0193(6)
C240.7044(3)0.5595(3)0.7070(2)0.0227(6)
H240.6865320.6237280.7517090.027*
C250.6853(3)0.5506(2)0.5986(2)0.0223(6)
H250.6552930.6098320.5706640.027*
C260.7232(4)0.5576(3)0.9225(2)0.0270(7)
H26A0.7835590.6331480.9260340.040*
H26B0.7396330.5447840.9935710.040*
H26C0.6144480.5530900.8948980.040*

Source of material

4-Methyl-3-thiosemicarbazide (Alfa Aesar), 4-(4-methoxyphenyl)-2-butanone (Sigma Aldrich), zinc acetate dihydrate (Fluka), absolute ethanol (Merck) and acetonitrile (Merck) were of analytical grade and used as purchased. The Schiff base ligand, LH, was prepared as described in the literature [5]. Zinc acetate dihydrate (0.220 g, 10 mmol) was dissolved in hot ethanol (20 mL) and added to a solution of LH (0.530 g, 20 mmol) in hot absolute ethanol (20 mL) while stirring for 30 min. The white precipitate was filtered, washed with cold ethanol and dried in vacuo. Single crystals were grown at room temperature from the slow evaporation of an acetonitrile/absolute ethanol (2:1 v/v) solution. Yield: 89%. M. Pt: 434–435 K. FT-IR (ATR (solid) cm−1): 3366 ν(N—H), 1606 ν(C=N), 1239 ν(N—N), 516 ν(Zn—N), 439 ν(Zn—S). UV-Visible: λmax (nm; ϵ (L mol−1 cm−1)): 239 (76,913), 279 (51,641). ICP-AES: Experimental %Zn = 11.05, Theoretical %Zn = 11.00.

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 N-bound H atoms were refined with N—H = 0.88 ± 0.01 Å, and with Uiso(H) = 1.2Ueq(N).

Comment

Metal complexes derived from thiosemicarbazones, R1R2C=N—N(R3)—C(=S)NR4R5, for R1–5 = H/alkyl/aryl have huge potential variability in composition and many are well-documented as having therapeutic applications and for their use as imaging agents [6]. Among the former, zinc(II) complexes are prominent with reports of their potential as anti-bacterial [7], anti-cancer [8] and anti-viral [9] agents. In continuation of biological studies of different metal complexes of thiosemicarbazones [10] and of supporting structural studies of zinc thiosemicarbazones [11], [12], herein the synthesis, characterisation as well as the crystal and molecular structures of Zn[(4-MeOC6H4)CH2CH2C(Me)=NN=C(S)N(H)Me]2, (I), are described.

The molecular structure of (I) is shown in the figure (70% displacement ellipsoids) which shows the zinc(II) centre to be bis-chelated in a N,S-fashion by two mono-anionic thiosemicarbazato ligands. For the S1-ligand, the Zn—S1 [2.2680(9) Å] and Zn—N3 [2.065(2) Å] bond lengths are shorter and longer, respectively, than the equivalent Zn—S2 [2.2739(8) Å] and Zn—N6 [2.038(2) Å] bonds for the S2-ligand. Compared with the structure of the uncoordinated ligand [5], the C—S [C1—S1 = 1.760(3) Å and C14—S2 = 1.755(3) Å] and [C1 = N2 = 1.308(4) Å and C14 = N5 = 1.310(3) Å] bond lengths in (I) have elongated and shortened, respectively, compared with the C1 = S1 [1.6943(13) & 1.6881(13) Å for the two independent molecules] and C1—N2 [1.3563(17) & 1.3616(17) Å] bond lengths of the acid, confirming the newly formed thiolate and imine bonds in (I) (see the figure).

The N2S2 at Zn donor set defines an approximate tetrahedral geometry with the range of angles being 87.10(7)° for the S1—Zn—N3 chelate angle to 127.45(7)° for S1—Zn—N6. The mode of coordination of the ligands leads to the formation of five-membered chelate rings. These are best described as having an envelope conformation with Zn lying 0.131(4) Å out of the least-squares plane defined by the remaining four atoms [r.m.s. deviation = 0.018 Å] for the S1-ligand. The envelope description is more pronounced for the S2-ligand with the equivalent parameters being 0.229(4) and 0.006 Å, respectively. The dihedral angle formed between the best planes through the rings is 79.95(5)°.

As discussed recently [11], are now more than ten known mononuclear complexes described by the general formula Zn[SC(NHR4)=NNCR1R2]2 where the R groups are non-coordinating and which crystallise solvent-free. To a first approximation, each of these structures resembles (I) but, with varying degrees of distortion from the ideal tetrahedral geometry evident, as manifested in the dihedral angle between the chelate rings. The chelate/chelate angles in the literature structures vary from 60.10(5) to 89.65(5)°. Interestingly, these angles are calculated for the two independent molecules in the asymmetric unit of the complex with R1 = R4 = Ph and R2 = Me [13], suggesting an influence of molecular packing effects on the adopted conformation.

In the crystal of (I), thioamide-N—H⋯O(methoxy) hydrogen bonds [N1—H1n⋯O1i: H1n⋯O1i = 2.32(2) Å, N1⋯O1i = 3.187(3) Å with angle at H1n = 174(3)° and N4—H4n⋯O2ii: H4n⋯O2ii = 2.19(2) Å, N4⋯O2ii = 3.049(3) Å with angle at H4n = 166(2)° for symmetry operations (i) 1 + x, y, 1 + z and (ii) x, y, −1 + z] are formed and lead to supramolecular layers perpendicular to [0 1 0]. In accord with the distance criteria in PLATON [14], no further directional interactions are apparent. Globally, centrosymmetrically related layers assemble into double-layers and inter-digitate along the b-axis.

A further analysis of the molecular packing was performed utilising Crystal Explorer 17 [15] and calculating the Hirshfeld surface and two-dimensional fingerprint plots (full and delineated) following literature procedures [16]. Consistent with the above description of the molecular packing, H⋯H contacts contribute 59.8% of all contacts to the surface. The most striking feature of the fingerprint plots are the well-defined spikes owing to the N—H⋯O hydrogen bonding. However, all H⋯O/O⋯H contacts contribute only 6.5% to the overall Hirshfeld surface. More prominent are H⋯C/C⋯H [14.3%] and H⋯S/S⋯S [11.9%] contacts; H⋯N/N⋯H [2.7%] contacts make only a minor contribution.

Acknowledgements

The X-ray intensity data were collected by Mohamed I. M. Tahir, Universiti Putra Malaysia. The synthetic part of this research was supported by the Research University Grant Scheme (RUGS Nos. 9199834 and 9174000) and the Malaysian Ministry of Science, Technology and Innovation (Grant No. 09-02-04-0752-EA001). 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: 2020-07-21
Accepted: 2020-08-13
Published Online: 2020-08-21
Published in Print: 2020-10-27

©2020 Ming Yueh Tan et al., published by De Gruyter, Berlin/Boston

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

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  34. The crystal structure of (E)-1-(quinolin-2-ylmethyl)-2-((1-(quinolin-2-ylmethyl)pyridin-2(1H)-ylidene)amino)pyridin-1-ium, C30H25BrN5
  35. Crystal structure of catena-poly[(μ2-1-((benzotriazol-1-yl)methyl)-1H-1,3-imdazole-κ2N:N′)-(1-((benzotriazol-1-yl)methyl)-1H-1,3-imdazole-κ1N)-(methanol-κ1O)mercury(II)] dinitrate, C21H22N12O7Hg
  36. Crystal structure of 1-(6-hydroxy-2-phenylbenzofuran-5-yl)ethan-1-one, C16H12O3
  37. The crystal structure of oxonium hexaquaaluminium disulfate hexahydrate
  38. Crystal structure of catena{(μ2-1,10-phenanthroline-κ4N,N,N′,N′)-(μ2-1,10-phenanthroline-κ3N,N,N′)potassium(I) {[bis(2-hydroxyethyl)iminiumyl](sulfanidyl)methyl}sulfanide hemi(1,10-phenanthroline)}, {C24H16KN4, 0.5(C12H8N2), C5H10NO2S2}
  39. Crystal structure of chlorido-[(N,N-di-isobutyl)dithiocarbamato-κ2S,S′]-di(4-methylbenzyl-κC)tin(IV), C25H36ClNS2Sn
  40. Crystal structure of chlorido-(η5-pentamethylcyclopentadienyl)-(4-chloro-4-pyridyl-2,2′:6′,2′′-terpyridine-κ2N,N′) rhodium(III) hexaflourophosphate, C31H29Cl2F6N3PRh
  41. The crystal structure of catena-poly[bis-(3,5-dinitro-1,2,4-triazolato-κ2N:O)-(μ2-1,4-bis(1-imidazolyl)benzene-κ2N:N′)copper(II)], C16H10CuN14O8
  42. Crystal structure of poly[triaqua-bis(μ3-3,3′-((5-carboxylato-1,3-phenylene)bis(oxy))dibenzoato)-tris(1,10-phenanthroline)cobalt(II)], C78H46N6O20Co3
  43. The crystal structure of 2,4-dihydroxybenzoic acid–nicotinamide–methanol (1/1/1), C15H18N2O6
  44. The crystal structure of aqua{N,N,N′,N′-tetrakis[(1H-benzimidazol-κN3) methyl]cyclohexane-1,2-diamine}lead(II) diacetate–methanol (1/2), C44H54N10O7Pb
  45. Crystal structure of (2-amino-5-bromo-3-iodophenyl)(3-(4-chlorophenyl)oxiran-2-yl)methanone, C15H10BrClINO2
  46. Synthesis and crystal structure of 3-octyl-5,5-diphenylimidazolidine-2,4-dione, C23H28N2O2
  47. Synthesis and crystal structure of 2-azido-N-(4-nitrophenyl)acetamide, C8H7N5O3
  48. Crystal structure of tert-butyl (1S,2R,5R)-2-(hydroxymethyl)-4-(4-methoxyphenyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate, C17H23NO5
  49. Crystal structure of 4-[(4-methoxy-2-nitrophenyl)carbamoyl]butanoic acid, C12H14N2O6
  50. Crystal structure of 3-ethyl-1-[(E)-[(2E)-3-phenylprop-2-en-1-ylidene]amino]thiourea, C12H15N3S
  51. Crystal structure of 4,4′-bipyridin-1,1′-dium poly[bis(μ4-benzene-1,3,5-triyltris(hydrogen phosphonato-κ4O:O′:O′′:O′′′))zinc(II)], C11H11NO9P3Zn
  52. Crystal structure of (μ2-1,1′-bis(diphenylphosphino)butane-κ2P,P′)-bis[(Z)-N-(3-fluorophenyl)-O-methylthiocarbamato-κS]-di-gold(I), C44H42Au2F2N2O2P2S2
  53. Crystal structure of (μ2-1,1′-bis(diphenylphosphino)hexane-κ2P,P′)-bis[(Z)-N-(3-fluorophenyl)-O-methylthiocarbamato-κS]digold(I), C46H46Au2F2N2O2P2S2
  54. Crystal structure of tetrakis (N-(2-hydroxyethyl)-N-isopropylcarbamodithioato-κS,S′)-(μ2(2-(pyridin-4-yl)vinyl)pyridine-κN,N′)dicadmium(II), C36H58Cd2N6O4S8
  55. Crystal structure of 4-(2-(benzo[b]thiophen-2-yl)-3,3,4,4,5,5-hexafluorocyclopent-1-en-1-yl)-1,5-dimethyl-1H-pyrrole-2-carbonitrile, C20H12F6N2S
  56. Crystal structure of bis(octahydrocyclopenta[c]pyrrolium)pentachlorobismuthate(III), (C7NH14)2BiCl5
  57. The crystal structure of diaqua-tris(nitrato-κ2O,O′)-bis(4,4,5,5-tetramethyl-2-(p-pyridyl)imidazoline-1-oxyl 3-oxide-κN)samarium(III), C24H36N9O15Sm
  58. Synthesis and crystal structure of methyl 2-(2-((tert-butoxycarbonyl)amino)phenyl)-2-(4-oxo-4H-chromen-3-yl)acetate, C23H23NO6
  59. Crystal structure of O-hexyl benzoylcarbamothioate, C14H19NO2S
  60. Crystal structure of chlorido-(O-methyl phenylcarbamothioamide-κS)-bis(triphenylphosphane-κP)silver(I), C44H39AgClNOP2S
  61. Crystal structure of chlorido-(O-ethyl phenylcarbamothioamide-κS)-bis(triphenylphosphane-κP)-silver(I), C45H41AgClNOP2S
  62. Crystal structure of 4-[(2-methoxyphenyl)carbamoyl]butanoic acid, C12H15NO4
  63. Crystal structure of ethyl 4-methyl-2-oxo-5-phenyl-1,3,4-oxadiazinane-3-carboxylate, C13H16N2O4
  64. Crystal structure of catena-poly[diaqua(μ2-2-(hydroxymethyl)-1H-imidazole-4,5-dicarboxylato)cadmium(II)], C6H8CdN2O7
  65. Crystal structure of (1S)-N-(chloromethyl)-1-((4S,6aR,8aS, 8bR,9aR)-4-methoxy-6a,8a-dimethyl-1,3,4, 5,6,6a,6b,7,8,8a,9a,10,10a,10b-tetradecahydro-8bH-naphtho[2′,1′:4,5] indeno[1,2-b]oxiren-8b-yl)-N-methylethan-1-amine, C24H46ClNO5
  66. Crystal structure of 4-[(3,5-dichlorophenyl)carbamoyl]butanoic acid, C11H11Cl2NO3
  67. Crystal structure of (2Z)-2-amino-3-[(E)-[(2,4-dihydroxyphenyl)methylidene]-amino]but-2-enedinitrile, C11H8N4O2
  68. Crystal structure of 3-methyl-1-[(E)-(4-phenylbutan-2-ylidene)amino]thiourea, C12H17N3S
  69. Crystal structure of carbonyl{hydridotris[3-phenyl-5-methylpyrazol-1-yl]borato-κ3N,N′N′′}copper(I), C31H28BCuN6O
  70. Crystal structure of ethane-1,2-diylbis(diphenylphosphine oxide) – dihydrogenperoxide (1/2), C26H28O6P2
  71. Crystal structure of 2-(pyridin-2-ylamino)pyridinium chloride dibenzyldichlorostannane, [C10H10N3]Cl, C14H14Cl2Sn
  72. Crystal structure of 4-[(3-methoxyphenyl)carbamoyl]butanoic acid, C12H15NO4
  73. Crystal structure of dichlorido-bis(tri-4-tolylphosphane oxide-κO)-di(4-chlorophenyl-κC)tin(IV), C54H50Cl4O2P2Sn
  74. Crystal structure of dichloridodimethylbis(tri-4-tolylphosphane oxide-κO)-tin(IV), C44H48Cl2O2P2Sn
  75. Crystal structure of chlorido(2-methylquinolin-8-olato-κ2N,O)-bis(4-tolyl-κC)tin(IV), C24H22ClNOSn
  76. Crystal structure of (E)-dichloro(1-chloro-3-methoxyprop-1-en-2-yl)(4-methoxyphenyl)-λ4-tellane, C11H13Cl3O2Te
  77. Crystal structure of bis{N-methyl-N′-[3-(4-methoxyphenyl)-1-methylpropane-1-ylidene]carbamohydrazonothioato}zinc(II), C26H36N6O2S2Zn
  78. Crystal structure of (2-carboxy-4-(3-carboxy-5-carboxylatophenoxy)benzoato-κ2O,O′)bis(1,10-phenantroline-κ2N,N′)cobalt(II), C40H24N4O9Co
  79. The crystal structure of (3S,8R,10R,14R)-17-((2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl)-4,4,8,10,14-pentamethyl-12-oxohexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate, C32H52O5
  80. Crystal structure of (μ2-1,1′-bis(diphenylphosphino)ferrocene-κ2P,P′)-bis[(Z)N-(3-fluorophenyl)-O-methylthiocarbamato-S]digold(I) chloroform solvate, C50H42Au2F2FeN2O2P2S2, CHCl3
  81. Crystal structure of poly[bis(μ2-1,4-di(1H-imidazol-1-yl)benzene-κ2N:N′)-(μ2-tetraoxidomolybdato(VI)-κ2O:O′)cobalt(II)], C24H20N8O4MoCo
https://doi.org/10.1515/ncrs-2020-0381
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Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of poly[tetraaqua-bis(μ4-5-(4-carboxy-benzylamino)-isophthalato-κ4O,O′:O′′:O′′′)-(μ2-4,4′-di(1H-imidazol-1-yl)-1,1′-biphenyl-κ2N:N′)dicadmium(II)], C25H22N3O8Cd
  3. The crystal structure of 2-(2-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-2-ium-1-yl)phenoxy)acetate, C19H18N2O3
  4. Crystal structure of poly[aqua-μ2-4,4′-bipyridine-κ2N:N′)-μ2-bis(2-(2-((2,6-dichlorophenyl)amino)phenyl)acetato-κ2O,O′)zinc(II)], C38H28Cl4N4O4Zn
  5. Crystal structure of 1-(2-(1H-indol-3-yl)ethyl)-4-benzyl-3-hydroxy-3,6-diphenylpiperazine-2,5-dione, C33H29N3O3
  6. The crystal structure 2,2′-bipyridine-κ2N,N′-(2-(3-amino-4-chlorobenzoyl)benzoato-κ1O)-(2-(3-amino-4-chlorobenzoyl)benzoato-κ2O,O′)zinc(II) — ethanol (1/1), C40H32Cl2N4O7Zn
  7. Crystal structure of catena-poly[(μ3-2-carboxy-4-(3-carboxy-5-carboxylatophenoxy)benzoato-κ3O:O′:O′′)-bis(μ2-4,4′-bis(pyrid-4-yl)biphenyl-k1N)copper(II)], C60H40N4O9Cu
  8. The crystal structure of dimethylammonium catena-[di(μ-aqua)-bis(μ9-benzene-1,3,5-tricarboxylato)pentalithium], C20H16Li5NO13
  9. Crystal structure of tetraaqua-bis(3,5-di(pyridin-4-yl)-1,2,4-triazol-1-ido-κ1N)nickel(II) dihydrate, C24H28O6N10Ni
  10. The crystal structure of tetrakis(1-methylimidazole-κ1N)-oxido-(sulfato-κ1O)vanadium(IV), C16H24N8O5SV
  11. Crystal structure of methyl 2-(6,11-dioxo-2,3,6,11-tetrahydro-1H-benzo[f]pyrrolo[2,1-a]isoindole-5-carbonyl)benzoate, C24H17NO5
  12. Crystal structure of (E)-N′-(2-hydroxy-4-(2-(piperidin-1-yl)ethoxy)benzylidene) nicotinohydrazide monohydrate, C20H24N4O3 ⋅ H2O
  13. Crystal structure of poly[bis(μ3-(1-(3,5-di(1H-imidazol-1-yl)phenyl)-1H-imidazole-κ3N:N′:N′′)cobalt(II)] dinitrate — N,N-dimethylformamide (1/4), C42H52N18O10Co
  14. The crystal structure bis{hexakis(1-methyl-1H-imidazole-κ1N)cobalt(II)} tetrakis(μ3-oxido)-octakis(μ2-oxido)-tetradecaoxido-octamolybdate(VI), C24H36CoMo4N12O13
  15. Crystal structure of di-μ-nicotinato-κ2N:O; κ2O:N-bis-[aqua-bis(benzyl)(nicotinato-κ2O,O′)tin(IV)], C52H48N4O10Sn2
  16. Crystal structure of dichlorido-bis[2-(2-(3-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)phenoxy)benzoic acidmanganese(II) monohydrate, C40H30N8O7MnCl2
  17. The crystal structure of benzyl 3β-acetylglycyrrhetate, C39H54O5
  18. Synthesis and crystal structure of (E)-1-benzyl-3-(4-methoxystyryl)quinoxalin-2(1H)-one, C24H20N2O2
  19. Crystal structure of trans-dichloridobis(4-chlorophenyl-κC1)(1,10-phenanthroline-κ2N,N′)tin(IV) dimethylsulphoxide solvate, C26H22Cl4N2OSSn
  20. Crystal structure of phenyl(1,3,4a-triphenyl-4a,5,6,10b-tetrahydro-1H-[1,4]oxazino[2,3-c]quinolin-5-yl)methanone, C36H28N2O2
  21. Crystal structure of (4aS,5S,6aS,6a1S, 10aS)-4a,5,6a,6a1,9,10-hexahydro-7H-4,5-methanocyclobuta[4,5]naphtho[8a,1-b]pyran-6(2H)-one, C15H16O2
  22. Crystal structure of [(Z)-O-isopropyl N-(4-chlorophenyl)thiocarbamato-κS]-(triphenylphosphine-κP)-gold(I), C28H26AuClNOPS
  23. Crystal structure of (μ2-1,1′-bis(diphenylphosphino)ferrocene-P,P′)-bis[(Z)-O-isopropyl N-(4-chlorophenyl)thiocarbamato-S]-di-gold(I) acetonitrile di-solvate, C54H50Au2Cl2FeN2O2P2S2⋅2(C2H3N)
  24. Crystal structure of (6aR,6a1S,10aS)-2,4a,6a,6a1,9,10-hexahydro-7H-4,5-methanocyclobuta[4,5]naphtho[8a,1-b]pyran, C15H16O
  25. Crystal structure of 5,17-diformyl-25,26,27,28-tetrahydroxycalix[4]arene- dichloromethane, C31H26Cl2O6
  26. Crystal structure of 2-tert-butyl 1-methyl 5-{4-[(methoxycarbonyl)amino]phenyl}-2,5-dihydro-1H-pyrrole-1,2-dicarboxylate, C19H24N2O6
  27. Crystal structure of [2-carboxybenzene-1-thiolato-S]-(triethylphosphane-P)-gold(I), C13H20AuO2PS
  28. Synthesis and crystal structure of bis(5-methyl-2-aldehyde-phenolato-κ2O1,O2)copper(II), C16H14CuO4
  29. Crystal structure of poly[triaqua-(di(2,2′-bipyridine-κ2N,N′)-μ4-silanetetrayltetrakis(benzene-4,1-diyl)tetrakis (hydrogen phosphonato)-κ4O:O′:O′′:O′′′) dicadmium(II)], C44H42N4O15P4Cd2Si
  30. Crystal structure of bis[μ2-(N,N-diethylcarbamodithioato-κS:κS,κS′)]-bis(triethylphosphine-P)-di-silver(I), C22H50Ag2N2P2S4
  31. Crystal structure of bis[μ2-(pyrrolidine-1-carbodithioato-κS:κS,κS′)]-bis(triethylphosphine-κP)disilver(I), C22H46Ag2N2P2S4
  32. Crystal structure of bis[μ2-(N-(2-hydroxyethyl)-N-methylcarbamodithioato-κS:κS,κS′)]-bis(triethylphosphine-P)-di-silver(I), C20H46Ag2N2O2P2S4
  33. The crystal structure of (2E,2′E)-,2,2′-bis[1-(2-pyrazinyl)ethylidene]carbonimidic dihydrazide, C13H15N9
  34. The crystal structure of (E)-1-(quinolin-2-ylmethyl)-2-((1-(quinolin-2-ylmethyl)pyridin-2(1H)-ylidene)amino)pyridin-1-ium, C30H25BrN5
  35. Crystal structure of catena-poly[(μ2-1-((benzotriazol-1-yl)methyl)-1H-1,3-imdazole-κ2N:N′)-(1-((benzotriazol-1-yl)methyl)-1H-1,3-imdazole-κ1N)-(methanol-κ1O)mercury(II)] dinitrate, C21H22N12O7Hg
  36. Crystal structure of 1-(6-hydroxy-2-phenylbenzofuran-5-yl)ethan-1-one, C16H12O3
  37. The crystal structure of oxonium hexaquaaluminium disulfate hexahydrate
  38. Crystal structure of catena{(μ2-1,10-phenanthroline-κ4N,N,N′,N′)-(μ2-1,10-phenanthroline-κ3N,N,N′)potassium(I) {[bis(2-hydroxyethyl)iminiumyl](sulfanidyl)methyl}sulfanide hemi(1,10-phenanthroline)}, {C24H16KN4, 0.5(C12H8N2), C5H10NO2S2}
  39. Crystal structure of chlorido-[(N,N-di-isobutyl)dithiocarbamato-κ2S,S′]-di(4-methylbenzyl-κC)tin(IV), C25H36ClNS2Sn
  40. Crystal structure of chlorido-(η5-pentamethylcyclopentadienyl)-(4-chloro-4-pyridyl-2,2′:6′,2′′-terpyridine-κ2N,N′) rhodium(III) hexaflourophosphate, C31H29Cl2F6N3PRh
  41. The crystal structure of catena-poly[bis-(3,5-dinitro-1,2,4-triazolato-κ2N:O)-(μ2-1,4-bis(1-imidazolyl)benzene-κ2N:N′)copper(II)], C16H10CuN14O8
  42. Crystal structure of poly[triaqua-bis(μ3-3,3′-((5-carboxylato-1,3-phenylene)bis(oxy))dibenzoato)-tris(1,10-phenanthroline)cobalt(II)], C78H46N6O20Co3
  43. The crystal structure of 2,4-dihydroxybenzoic acid–nicotinamide–methanol (1/1/1), C15H18N2O6
  44. The crystal structure of aqua{N,N,N′,N′-tetrakis[(1H-benzimidazol-κN3) methyl]cyclohexane-1,2-diamine}lead(II) diacetate–methanol (1/2), C44H54N10O7Pb
  45. Crystal structure of (2-amino-5-bromo-3-iodophenyl)(3-(4-chlorophenyl)oxiran-2-yl)methanone, C15H10BrClINO2
  46. Synthesis and crystal structure of 3-octyl-5,5-diphenylimidazolidine-2,4-dione, C23H28N2O2
  47. Synthesis and crystal structure of 2-azido-N-(4-nitrophenyl)acetamide, C8H7N5O3
  48. Crystal structure of tert-butyl (1S,2R,5R)-2-(hydroxymethyl)-4-(4-methoxyphenyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate, C17H23NO5
  49. Crystal structure of 4-[(4-methoxy-2-nitrophenyl)carbamoyl]butanoic acid, C12H14N2O6
  50. Crystal structure of 3-ethyl-1-[(E)-[(2E)-3-phenylprop-2-en-1-ylidene]amino]thiourea, C12H15N3S
  51. Crystal structure of 4,4′-bipyridin-1,1′-dium poly[bis(μ4-benzene-1,3,5-triyltris(hydrogen phosphonato-κ4O:O′:O′′:O′′′))zinc(II)], C11H11NO9P3Zn
  52. Crystal structure of (μ2-1,1′-bis(diphenylphosphino)butane-κ2P,P′)-bis[(Z)-N-(3-fluorophenyl)-O-methylthiocarbamato-κS]-di-gold(I), C44H42Au2F2N2O2P2S2
  53. Crystal structure of (μ2-1,1′-bis(diphenylphosphino)hexane-κ2P,P′)-bis[(Z)-N-(3-fluorophenyl)-O-methylthiocarbamato-κS]digold(I), C46H46Au2F2N2O2P2S2
  54. Crystal structure of tetrakis (N-(2-hydroxyethyl)-N-isopropylcarbamodithioato-κS,S′)-(μ2(2-(pyridin-4-yl)vinyl)pyridine-κN,N′)dicadmium(II), C36H58Cd2N6O4S8
  55. Crystal structure of 4-(2-(benzo[b]thiophen-2-yl)-3,3,4,4,5,5-hexafluorocyclopent-1-en-1-yl)-1,5-dimethyl-1H-pyrrole-2-carbonitrile, C20H12F6N2S
  56. Crystal structure of bis(octahydrocyclopenta[c]pyrrolium)pentachlorobismuthate(III), (C7NH14)2BiCl5
  57. The crystal structure of diaqua-tris(nitrato-κ2O,O′)-bis(4,4,5,5-tetramethyl-2-(p-pyridyl)imidazoline-1-oxyl 3-oxide-κN)samarium(III), C24H36N9O15Sm
  58. Synthesis and crystal structure of methyl 2-(2-((tert-butoxycarbonyl)amino)phenyl)-2-(4-oxo-4H-chromen-3-yl)acetate, C23H23NO6
  59. Crystal structure of O-hexyl benzoylcarbamothioate, C14H19NO2S
  60. Crystal structure of chlorido-(O-methyl phenylcarbamothioamide-κS)-bis(triphenylphosphane-κP)silver(I), C44H39AgClNOP2S
  61. Crystal structure of chlorido-(O-ethyl phenylcarbamothioamide-κS)-bis(triphenylphosphane-κP)-silver(I), C45H41AgClNOP2S
  62. Crystal structure of 4-[(2-methoxyphenyl)carbamoyl]butanoic acid, C12H15NO4
  63. Crystal structure of ethyl 4-methyl-2-oxo-5-phenyl-1,3,4-oxadiazinane-3-carboxylate, C13H16N2O4
  64. Crystal structure of catena-poly[diaqua(μ2-2-(hydroxymethyl)-1H-imidazole-4,5-dicarboxylato)cadmium(II)], C6H8CdN2O7
  65. Crystal structure of (1S)-N-(chloromethyl)-1-((4S,6aR,8aS, 8bR,9aR)-4-methoxy-6a,8a-dimethyl-1,3,4, 5,6,6a,6b,7,8,8a,9a,10,10a,10b-tetradecahydro-8bH-naphtho[2′,1′:4,5] indeno[1,2-b]oxiren-8b-yl)-N-methylethan-1-amine, C24H46ClNO5
  66. Crystal structure of 4-[(3,5-dichlorophenyl)carbamoyl]butanoic acid, C11H11Cl2NO3
  67. Crystal structure of (2Z)-2-amino-3-[(E)-[(2,4-dihydroxyphenyl)methylidene]-amino]but-2-enedinitrile, C11H8N4O2
  68. Crystal structure of 3-methyl-1-[(E)-(4-phenylbutan-2-ylidene)amino]thiourea, C12H17N3S
  69. Crystal structure of carbonyl{hydridotris[3-phenyl-5-methylpyrazol-1-yl]borato-κ3N,N′N′′}copper(I), C31H28BCuN6O
  70. Crystal structure of ethane-1,2-diylbis(diphenylphosphine oxide) – dihydrogenperoxide (1/2), C26H28O6P2
  71. Crystal structure of 2-(pyridin-2-ylamino)pyridinium chloride dibenzyldichlorostannane, [C10H10N3]Cl, C14H14Cl2Sn
  72. Crystal structure of 4-[(3-methoxyphenyl)carbamoyl]butanoic acid, C12H15NO4
  73. Crystal structure of dichlorido-bis(tri-4-tolylphosphane oxide-κO)-di(4-chlorophenyl-κC)tin(IV), C54H50Cl4O2P2Sn
  74. Crystal structure of dichloridodimethylbis(tri-4-tolylphosphane oxide-κO)-tin(IV), C44H48Cl2O2P2Sn
  75. Crystal structure of chlorido(2-methylquinolin-8-olato-κ2N,O)-bis(4-tolyl-κC)tin(IV), C24H22ClNOSn
  76. Crystal structure of (E)-dichloro(1-chloro-3-methoxyprop-1-en-2-yl)(4-methoxyphenyl)-λ4-tellane, C11H13Cl3O2Te
  77. Crystal structure of bis{N-methyl-N′-[3-(4-methoxyphenyl)-1-methylpropane-1-ylidene]carbamohydrazonothioato}zinc(II), C26H36N6O2S2Zn
  78. Crystal structure of (2-carboxy-4-(3-carboxy-5-carboxylatophenoxy)benzoato-κ2O,O′)bis(1,10-phenantroline-κ2N,N′)cobalt(II), C40H24N4O9Co
  79. The crystal structure of (3S,8R,10R,14R)-17-((2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl)-4,4,8,10,14-pentamethyl-12-oxohexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate, C32H52O5
  80. Crystal structure of (μ2-1,1′-bis(diphenylphosphino)ferrocene-κ2P,P′)-bis[(Z)N-(3-fluorophenyl)-O-methylthiocarbamato-S]digold(I) chloroform solvate, C50H42Au2F2FeN2O2P2S2, CHCl3
  81. Crystal structure of poly[bis(μ2-1,4-di(1H-imidazol-1-yl)benzene-κ2N:N′)-(μ2-tetraoxidomolybdato(VI)-κ2O:O′)cobalt(II)], C24H20N8O4MoCo
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