Home Crystal structure of chlorido-(O-methyl phenylcarbamothioamide-κS)-bis(triphenylphosphane-κP)silver(I), C44H39AgClNOP2S
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Crystal structure of chlorido-(O-methyl phenylcarbamothioamide-κS)-bis(triphenylphosphane-κP)silver(I), C44H39AgClNOP2S

  • Chien Ing Yeo , Sin-Yeang Teow , Li Yuan Liew , Jactty Chew and Edward R.T. Tiekink ORCID logo EMAIL logo
Published/Copyright: September 18, 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

C44H39AgClNOP2S, triclinic, P1̄ (no. 2), a = 10.2520(3) Å, b = 13.2252(4) Å, c = 14.9378(3) Å, α = 78.424(2)°, β = 78.388(2)°, γ = 84.534(3)°, V = 1940.35(9) Å3, Z = 2, Rgt(F) = 0.0382, wRref(F2) = 0.0807, T = 100(2) K.

CCDC no.: 2022654

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 prism
Size:0.10 × 0.05 × 0.05 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.76 mm−1
Diffractometer, scan mode:SuperNova, ω
θmax, completeness:27.6°, >99%
N(hkl)measured, N(hkl)unique, Rint:30490, 8967, 0.056
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 7094
N(param)refined:464
Programs:CrysAlisPRO [1], SHELX [2], [3], WinGX/ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
Ag0.86583(2)0.75024(2)0.25301(2)0.01561(6)
Cl11.11233(6)0.76342(5)0.25111(4)0.02003(15)
S10.84634(7)0.85009(6)0.07791(4)0.02095(16)
P10.81885(7)0.57098(5)0.25117(4)0.01358(14)
P20.73868(7)0.85804(5)0.36090(4)0.01349(14)
O11.01595(19)0.89720(14)−0.08262(11)0.0218(4)
N11.1105(2)0.82275(17)0.03710(13)0.0162(5)
H1N1.103(3)0.806(2)0.0975(7)0.019*
C10.9976(3)0.8567(2)0.00793(16)0.0169(6)
C21.2433(3)0.81508(19)−0.01460(17)0.0172(6)
C31.2723(3)0.7920(2)−0.10352(18)0.0222(6)
H31.20230.7859−0.13490.027*
C41.4042(3)0.7781(2)−0.14591(18)0.0265(7)
H41.42430.7629−0.20690.032*
C51.5071(3)0.7860(2)−0.10078(19)0.0267(7)
H51.59710.7753−0.13020.032*
C61.4778(3)0.8095(2)−0.01215(19)0.0268(7)
H61.54800.81530.01920.032*
C71.3465(3)0.8246(2)0.03047(17)0.0212(6)
H71.32670.84150.09080.025*
C80.9032(3)0.9457(2)−0.12306(18)0.0288(7)
H8A0.93480.9810−0.18700.043*
H8B0.85590.9961−0.08620.043*
H8C0.84250.8928−0.12340.043*
C110.9458(3)0.5006(2)0.17872(16)0.0154(5)
C121.0384(3)0.5580(2)0.11114(16)0.0188(6)
H121.03250.63130.10300.023*
C131.1397(3)0.5086(2)0.05535(18)0.0236(6)
H131.20260.54830.00950.028*
C141.1492(3)0.4022(2)0.06628(19)0.0272(7)
H141.21780.36870.02780.033*
C151.0578(3)0.3447(2)0.13389(19)0.0271(7)
H151.06440.27140.14180.033*
C160.9567(3)0.3931(2)0.19013(18)0.0227(6)
H160.89490.35290.23640.027*
C210.7937(3)0.48227(19)0.36336(16)0.0146(5)
C220.9039(3)0.4540(2)0.40765(17)0.0206(6)
H220.98960.47650.37700.025*
C230.8880(3)0.3936(2)0.49585(18)0.0247(7)
H230.96310.37410.52510.030*
C240.7633(3)0.3612(2)0.54176(18)0.0246(7)
H240.75290.31990.60240.029*
C250.6543(3)0.3891(2)0.49909(18)0.0244(7)
H250.56880.36730.53070.029*
C260.6689(3)0.4493(2)0.40979(17)0.0185(6)
H260.59350.46770.38070.022*
C310.6617(3)0.56835(19)0.21201(16)0.0142(5)
C320.5636(3)0.6443(2)0.23418(17)0.0192(6)
H320.58300.69620.26440.023*
C330.4379(3)0.6453(2)0.21282(18)0.0257(7)
H330.37070.69610.23000.031*
C340.4115(3)0.5712(2)0.16602(19)0.0282(7)
H340.32580.57150.15080.034*
C350.5091(3)0.4968(2)0.14138(18)0.0247(7)
H350.49090.44740.10800.030*
C360.6334(3)0.4941(2)0.16531(16)0.0191(6)
H360.69940.44170.14990.023*
C410.5712(3)0.89356(19)0.33661(17)0.0150(5)
C420.4550(3)0.8737(2)0.40218(18)0.0196(6)
H420.46020.84540.46510.023*
C430.3315(3)0.8951(2)0.37592(19)0.0229(6)
H430.25260.88050.42090.028*
C440.3224(3)0.9375(2)0.28490(19)0.0232(6)
H440.23750.95180.26730.028*
C450.4375(3)0.9590(2)0.21940(18)0.0224(6)
H450.43120.98880.15690.027*
C460.5615(3)0.9377(2)0.24410(17)0.0194(6)
H460.64000.95280.19880.023*
C510.8055(3)0.9804(2)0.36421(15)0.0147(5)
C520.9378(3)0.9765(2)0.37567(17)0.0199(6)
H520.98980.91290.37850.024*
C530.9935(3)1.0659(2)0.38290(17)0.0230(6)
H531.08331.06310.39140.028*
C540.9188(3)1.1587(2)0.37783(17)0.0241(7)
H540.95701.21930.38340.029*
C550.7887(3)1.1636(2)0.36475(18)0.0265(7)
H550.73811.22780.36010.032*
C560.7310(3)1.0743(2)0.35826(17)0.0209(6)
H560.64121.07770.34980.025*
C610.7131(3)0.79487(19)0.48370(16)0.0140(5)
C620.7242(3)0.6876(2)0.50624(17)0.0218(6)
H620.74310.64820.45800.026*
C630.7080(3)0.6375(2)0.59847(18)0.0274(7)
H630.71410.56410.61330.033*
C640.6828(3)0.6948(2)0.66869(18)0.0255(7)
H640.67350.66060.73180.031*
C650.6711(3)0.8014(2)0.64752(18)0.0259(7)
H650.65340.84040.69600.031*
C660.6852(3)0.8519(2)0.55508(17)0.0197(6)
H660.67590.92520.54060.024*

Source of material

To AgCl (Sigma Aldrich; 0.36 g, 2.5 mmol) in acetonitrile (25 mL) was added an equimolar quantity of MeOC(=S)N(H)Ph [5] (0.42 g, 2.5 mmol) in acetonitrile (25 mL), followed by addition of two moles equivalent of triphenylphosphane (Merck; 1.31 g, 5.0 mmol) in acetonitrile (25 mL). The resulting mixture was stirred for 3 h at 323 K, giving a white suspension. An equal volume of dichloromethane (75 mL) was added to the suspension and the clear solution that resulted was left for slow evaporation at room temperature, yielding colourless crystals after 1 week. Yield: 1.86 g (89%). M. pt. (Krüss KSP1N melting point meter): 425–427 K. Elemental Analysis for C44H39AgClNOP2S (Perkin Elmer PE 2400 CHN Elemental Analyser; %): C, 63.29; H, 4.71; N, 1.68. Found: C, 63.05; H, 4.62; N, 1.68. IR (Perkin Elmer Spectrum 400 FT Mid-IR/Far-IR spectrophotometer; cm−1): 3434 (br) ν(N—H), 1436 (s) ν(C—N), 1224 (s) ν(C—O), 1095 (s) ν(C=S). 1H NMR (Bruker Avance 400 MHz NMR spectrometer with chemical shifts relative to tetramethylsilane in CDCl3 solution at 298 K, ppm): δ 11.17 (s, br, 1H, NH), 7.41–7.20 (m, br, 35H, Ph3P, aryl-H), 4.02 (s, 3H, Me). 13C{1H} NMR (as for 1H NMR): δ 187.9 (Cq), 137.4 (Ph, Cipso), 134.0 (d, m-PC6H5, 3JCP = 16.47 Hz), 133.1 (d, i-PC6H5, 1JCP = 21.49 Hz), 129.8 (s, p-PC6H5), 128.8 (Ph, Cmeta), 128.7 (d, o-PC6H5, 2JCP = 9.23 Hz), 125.3 (Ph, Cpara), 122.4 (Ph, Cortho), 58.4 (OMe). 31P{1H} NMR (as for 1H NMR but with chemical shift referenced to 85% aqueous H3PO4 as the external reference): δ 5.4.

A preliminary screen for anti-bacterial activity was performed, again following literature protocols [6]. Compound (I) proved ineffective against the studied bacteria.

Experimental details

The C-bound H atoms were geometrically placed (C—H = 0.95–0.98 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). The N-bound H atom was refined with N—H = 0.88 ± 0.01 Å, and with 1.2Ueq(N).

Comment

The synthesis and characterisation of the title compound, (Ph3P)2Ag[S=C(OMe)N(H)Ph]Cl, (I), was motivated by the biological potential exhibited by their phosphanegold(I) thiolate counterparts of general formula R3PAu[SC(OR′)=NAr]. These have proven to be potent against bacteria, especially Gram-positive bacteria [7] and against a number of cancer cell lines, inducing cell death via apoptotic pathways [8].

The molecular structure of (I) is shown in the figure (70% displacement ellipsoids). The Ag atom is tetrahedrally coordinated by the Cl [2.5438(7) Å], thione-S [2.7201(7) Å] and two phosphane-P atoms [Ag—P1, P2 = 2.4702(7), 2.4600(7) Å]. The C1 = S1 and C1—N1 bond lengths in (I) of 1.685(3) and 1.326(3) Å, respectively, are similar to those of the uncoordinated acid, i.e. S=C(OMe)N(H)Ph [5], of 1.6708(11) and 1.3288(15) Å, respectively, confirming the thione form of the ligand in (I). The range of tetrahedral angles is from a small 100.95(2)°, for Cl1—Ag—S1, to a wide 125.07(2)° for P1—Ag—P2. The thiocarbamide molecule is orientated to place the amide-N—H in a position to form an intramolecular amide-N—H⋯Cl hydrogen bond [N1—H1n⋯Cl1: H1n⋯Cl1 = 2.270(12) Å, N1⋯Cl1 = 3.139(2) Å with angle at H1n = 173(3)°] to form a quasi six-membered ring.

The most closely related structure in the literature is found in the accompanying report which describes the structure of the O-ethyl analogue of (I) which displays the same basic molecular structure [9]. Further, there is the direct copper(I) analogue of (I) which, while not isostructural features a very similar geometry [10].

The molecular packing of (I) features phenyl-C—H⋯Cl interactions [C24—H24⋯Cl1i: H24⋯Cl1i = 2.81 Å, C24⋯Cl1i = 3.613(3) Å with angle at H24 = 143° and C33—H33⋯Cl1ii: H33⋯Cl1ii = 2.69 Å, C33⋯Cl1ii = 3.536(3) Å with angle at H33 = 149° for symmetry operations (i) 2 − x, 1 − y, 1 − z and (ii) −1 + x, y, z]. These interactions serve to link molecules into a linear, supramolecular chain along the a-axis. As there are no apparent directional interactions between the chains, a further analysis of the molecular packing was conducted by calculating the Hirshfeld surface and two-dimensional fingerprint plots with the aid of Crystal Explorer 17 [11] following established procedures [12].

The distinctive feature of the fingerprint plot are symmetric spikes due to the specified H⋯Cl/Cl⋯H interactions. Yet, these contacts contribute only 4.0% to the overall Hirshfeld surface. By far, the most prominent contacts are H⋯H contacts, contributing 62.8% followed by H⋯C/C⋯H contacts, at 28.0%. Finally, reflecting the lack of π⋯π stacking, C⋯C contacts contributed only 1.5% to the overall surface.

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: 2020-07-16
Accepted: 2020-08-11
Published Online: 2020-09-18
Published in Print: 2020-10-27

©2020 Chien Ing Yeo 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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  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-2020-0362
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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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