Startseite Naturwissenschaften The crystal structure of bis[μ2-(N,N-diethylcarbamodithioato-κS:κS,κS′)] bis[1′-(diphenylphosphino-κP)-1-cyanoferrocene]disilver(I), C56H56Ag2Fe2N4P2S4
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The crystal structure of bis[μ2-(N,N-diethylcarbamodithioato-κS:κS,κS′)] bis[1′-(diphenylphosphino-κP)-1-cyanoferrocene]disilver(I), C56H56Ag2Fe2N4P2S4

  • Karel Škoch und Petr Štěpnička EMAIL logo
Veröffentlicht/Copyright: 14. Juni 2019
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Zeitschrift für Kristallographie - New Crystal Structures
Aus der Zeitschrift Zeitschrift für Kristallographie - New Crystal Structures Band 234 Heft 5

Abstract

C56H56Ag2Fe2N4P2S4, triclinic, P1̄ (no. 2), a = 9.5058(2) Å, b = 10.8362(2) Å, c = 14.3325(3) Å, α = 72.400(1)°, β = 75.241(1)°, γ = 77.132(1)°, V = 1343.71(5) Å3, Z = 1, Rgt(F) = 0.0191, wRref(F2) = 0.0443, T = 150(2) K.

CCDC no.: 1903635

The molecular structure of the title complex 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:Orange prism
Size:0.30 × 0.17 × 0.15 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.50 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:27.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:20417, 6185, 0.020
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 5705
N(param)refined:318
Programs:Bruker [1], SHELX [2], [3], PLATON [4]
Table 2:

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

AtomxyzUiso*/Ueq
Ag0.11162(2)0.90051(2)0.57463(2)0.01796(4)
Fe−0.11330(2)0.76206(2)0.89548(2)0.01302(5)
N1−0.55587(17)0.81998(16)1.01630(12)0.0322(3)
P0.20444(4)0.84529(4)0.72532(3)0.01268(8)
C1−0.31474(17)0.70951(15)0.92414(11)0.0174(3)
C2−0.21470(17)0.60197(15)0.97083(12)0.0185(3)
H2−0.2250790.5603091.0402810.022*
C3−0.09777(18)0.56976(15)0.89391(12)0.0197(3)
H3−0.0155830.5021930.9029210.024*
C4−0.12438(18)0.65605(15)0.80056(12)0.0192(3)
H4−0.0629070.6553920.7369900.023*
C5−0.25747(18)0.74263(16)0.81851(11)0.0189(3)
H5−0.3009720.8103220.7695800.023*
C60.06622(16)0.85481(14)0.83626(11)0.0141(3)
C7−0.06676(17)0.94850(15)0.83569(12)0.0182(3)
H7−0.0969081.0092020.7781950.022*
C8−0.14568(19)0.93495(16)0.93588(13)0.0231(3)
H8−0.2374930.9850890.9570380.028*
C9−0.06328(18)0.83338(17)0.99877(12)0.0223(3)
H9−0.0909340.8035631.0693910.027*
C100.06746(17)0.78377(16)0.93847(11)0.0176(3)
H100.1424950.7156030.9616570.021*
C11−0.44800(18)0.77258(16)0.97521(12)0.0217(3)
C120.33119(16)0.94766(14)0.72864(11)0.0137(3)
C130.30902(19)1.00941(16)0.80477(12)0.0213(3)
H130.2258320.9980890.8580580.026*
C140.4082(2)1.08761(17)0.80307(13)0.0264(4)
H140.3929831.1286230.8555570.032*
C150.52867(18)1.10577(16)0.72537(13)0.0242(4)
H150.5962241.1591550.7243090.029*
C160.55046(18)1.04574(16)0.64902(14)0.0243(4)
H160.6326861.0588810.5951820.029*
C170.45319(17)0.96666(15)0.65059(12)0.0194(3)
H170.4697080.9251760.5982280.023*
C180.31212(16)0.68113(14)0.75418(11)0.0147(3)
C190.29954(19)0.58892(16)0.70804(12)0.0233(3)
H190.2304580.6097390.6658010.028*
C200.3877(2)0.46670(17)0.72365(14)0.0306(4)
H200.3781330.4039740.6924500.037*
C210.4895(2)0.43578(16)0.78438(13)0.0258(4)
H210.5503250.3524020.7942130.031*
C220.50246(18)0.52642(16)0.83077(12)0.0224(3)
H220.5719570.5052000.8727470.027*
C230.41401(17)0.64825(15)0.81598(12)0.0185(3)
H230.4229450.7099850.8483230.022*
S10.15840(4)0.74405(4)0.45708(3)0.02175(9)
S2−0.14019(4)0.86410(4)0.54578(3)0.01738(8)
N2−0.09257(16)0.69922(13)0.43191(10)0.0207(3)
C31−0.02935(17)0.76270(14)0.47264(11)0.0159(3)
C32−0.0051(2)0.60689(17)0.37386(13)0.0276(4)
H32A−0.0626280.5372710.3819900.033*
H32B0.0855720.5647770.4002300.033*
C330.0368(3)0.6748(2)0.26368(14)0.0504(6)
H33A−0.0526640.7178820.2376030.076*
H33B0.0916800.6098550.2272080.076*
H33C0.0984060.7404560.2550540.076*
C34−0.2521(2)0.72491(17)0.43508(14)0.0292(4)
H34A−0.2689580.7182790.3715180.035*
H34B−0.2908810.8158380.4401530.035*
C35−0.3375(2)0.6321(2)0.52105(18)0.0415(5)
H35A−0.3013750.5419010.5159180.062*
H35B−0.4423650.6545620.5183970.062*
H35C−0.3239750.6398950.5844750.062*

Source of material

1′-(Diphenylphosphino)-1-cyanoferrocene (L; 20 mg, 51 μmol) [5] and silver(I) N,N′-diethylcarbamodithioate (Sigma-Aldrich; 13 mg, 51 μmol) were mixed in chloroform (2 mL). The resulting mixture was stirred for 60 min and then evaporated under vacuum. The orange-brown residue was crystallized from ethyl acetate-hexane (2 + 10 mL) to afford the title compound as rusty orange, prismatic crystals (13 mg, 38%).

Characterization data: 1H NMR (400 MHz, CDCl3): δ 1.30 (t, 3JHH = 7.1 Hz, 6 H, CH3), 3.99 (q, 3JHH = 7.1 Hz, 4 H, CH2), 4.47 (appparent q, J′ = 1.9 Hz, 2 H, C5H4), 4.51 (appparent t, J′ = 1.9 Hz, 2 H, C5H4), 4.52 (appparent t, J′ = 1.8 Hz, 2 H, C5H4), 4.63 (appparent t, J′ = 1.8 Hz, 2 H, C5H4), 7.33−7.45 (m, 6 H, PPh2), 7.48–7.55 (m, 4 H, PPh2). 31P{1H} NMR (162 MHz, CDCl3): δ 1.9 (br s). ESI+ MS: m/z 502 ([Ag(L)]+). IR (Nujol, cm−1). νmax 3103 w, 3087 w, 3068 w, 2226 s, 1586 w, 1478 s, 1421 s, 1267 s, 1230 w, 1207 m, 1170 m, 1136 m, 1096 m, 1073 m, 1049 w, 985 m, 911 m, 842 m, 810 w, 776 w, 749 m, 744 m, 704 m, 695 s, 563 w, 532 w, 509 s, 482 s, 474 m, 459 m. Anal. Calc. for C56H56Ag2Fe2N4P2S4 × 0.2 CHCl3 (663.3): C 50.88, H 4.27, N 4.22%. Found C 50.64, H 4.17, N 3.99% (sample from chloroform).

Experimental details

The structure was solved by direct methods using SHELXS [2] and refined by full-matrix least-squares based on F2 with SHELXL [3]. All non-hydrogen atoms were refined anisotropically. Hydrogen atoms were included in their calculated positions and refined as riding atoms [3] with Uiso set to a multiple of Ueq of their bonding carbon atoms.

Comment

Dithiocarbamates have attracted attention as readily accessible and structurally changeable ligands for transition metal ions and have even found manifold practical use [6], [7], [8]. From a structural viewpoint, they are versatile donors than can coordinate as terminal and bridging ligands. The flexible coordination of dithiocarbamates can be demonstrated in their silver(I) complexes [8]. For instance, homoleptic Ag(I)-dithiocarbamate complexes, typically forming complicated polymeric coordination assemblies in the solid state, can be cleaved into smaller discrete species by addition of other ligands. The coordination of phosphine ligands to the polymeric Ag(I) dithiocarbamates gives rise to dimeric species with bridging dithiocarbamate ligands analogous to the title compound [9], [10], [11], [12], [13] or even to mononuclear complexes of the type [(R3P)2Ag(S2CNR2-κ2S,S′)] [10], [14], [15], depending on the amount and type of the auxiliary ligand.

Having recently demonstrated that 1′-(diphenylphosphino)-1-cyanoferrocene [1] can be accommodated in Ag(I) complexes as a P-monodentate (terminal), P,N-bridging and even P,N-chelating ligand [16], [17], we decided to extend our investigations further toward Ag(I) complexes containing a supporting dithiocarbamate ligand.

The reaction between equimolar quantities of the phosphinoferrocene nitrile Ph2PfcCN (fc = ferrocene-1,1′-diyl) and silver(I) N,N-diethylcarbamodithioate in chloroform produced the orange complex [Ag(Ph2PfcCN-κP)(μ-Et2NCS2-κS:κS,κS′)]2. The compound crystallizes with the symmetry of the triclinic space group P1̄ and with the complex molecule lying around the crystallographic inversion centres (Z = 1). Formally, the structure consists of two equivalent Ag(Ph2PfcCN-κP)(Et2NCS2-κS:κS′) fragments symmetrically interlinked into a dimeric assembly by a pair of additional Ag—S interactions. This gives rise to identical PS3 donor sets around the chemically identical Ag(I) centres. Expectedly, the Ag—S bonds involving the bridging sulfur atom S2 (Ag—S2 = 2.6608(5) Å, Ag—S2′ = 2.6394(4) Å) are slightly but statistically longer that the bonds involving the terminally coordinated sulfur atom S1 (Ag—S1 = 2.6308(4) Å), and this asymmetry is reflected also in the C—S distances (C31—S1 = 1.715(2) Å, C31—S2 = 1.742(2) Å). The central Ag2S2 ring, rather regular in terms of bond distances, is compressed along the Ag⋯Ag′ axis (cf. S2—Ag—S2′ = 101.63(1)°, Ag—S2—Ag′ = 78.37(1)°). Notably, the Ag⋯Ag′ distance of 3.3488(3) Å exceeds by far the sum the of covalent radii (2.9 Å) but still falls below the treshold of the van der Waals contacts (3.44 Å).

The coordination spheres around the silver atoms are severely distorted as evidenced by the dihedral angle of the {Ag,S2,S2′} and {Ag,P,S1} planes of 65.42(2)° that departs substantially from the 90° expected for a regular tetrahedron. The chelating dithiocarbamate ligand is associated with the smallest interligand angle of 68.55(1)° (S1—Ag—S2), and the P—Ag—S angles, ranging from 116.34(1)° for P—Ag—S2′ to 130.20(2) for P—Ag—S2, compensate for this closure.

The ferrocene ligands coordinate as simple phosphine donors. Hence, their nitrile substituents are rotated away from the Ag(I) centres. The torsion angle C1—Cg1—Cg2—C6, where Cg1 and Cg2 are the centroids of the cyclopentadienyl rings C(1−5) and C(6−10), respectively, is −157.8(1)°. The ferrocene moiety shows similar Fe—C distances (2.026(2)−2.063(2) Å) and, accordingly, a tilt angle of only 2.1(1)°. The P—Ag distance of 2.3990(5) Å in the title compound compares well with the value reported for the analogous triphenylphosphine complex (2.4125(4) Å) [10].

Acknowledgements

The authors thank Dr. Ivana Císařová for collecting the diffraction data and the Czech Science Foundation for financial support (project No. 17-02495S).

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Received: 2019-01-28
Accepted: 2019-03-16
Published Online: 2019-06-14
Published in Print: 2019-09-25

©2019 Karel Škoch et al., published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

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  45. Crystal structure of 3-[methyl(phenyl)amino]-1-phenylthiourea, C14H15N3S
  46. Crystal structure of 1-(4-chlorophenyl)-3-[methyl(phenyl)amino]thiourea, C14H14ClN3S
  47. Crystal structure of 2-tert-butyl-1H-imidazo[4,5-b]pyridine, C10H13N3
  48. Crystal structure of 5-carboxy-2-(2-carboxyphenyl)-1H-imidazol-3-ium-4-carboxylate dihydrate, C12H8N2O6⋅2(H2O)
  49. The crystal structure of dichlorido-μ2-dichlorido-(η2-1,4-bis(4-vinylbenzyl)-1,4-diazabicyclo[2.2.2]octane-1,4-diium)dicopper(I), C24H30N2Cu2Cl4
  50. Crystal structure of 4-bromobenzyl (Z)-N-(adamantan-1-yl)morpholine-4-carbothioimidate, C22H29BrN2OS
  51. Crystal structure of (4S,4aS,6aR,6bR,12aS,12bR,14aS,14bR)-3,3,6a,6b,9,9,12a-heptamethyloctadecahydro-1H,3H-4,14b-ethanophenanthro[1,2-h]isochromene-1(6bH)-one, C30H48O2
  52. Crystal structure of 3,5-bis(trifluoromethyl)benzyl (Z)-N′-(adamantan-1-yl)-4-phenylpiperazine-1-carbothioimidate, C30H33F6N3S
  53. The crystal structure of 3-methoxyphenanthridin-6(5H)-one, C14H11NO2
  54. Crystal structure of 4-(5,5-difluoro-1,3,7,9-tetramethyl-3H,5H-5λ4-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinin-10-yl)pyridin-1-ium tetraiodidoferrate(III), C18H19BF2FeI4N3
  55. Crystal structure of 2-(3-methoxyphenyl)-3-((phenylsulfonyl)methyl)imidazo[1,2-a]pyridine, C21H18N2O3S
  56. Crystal structure of [(2-(2-chlorophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κ2O,O′) (5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II) perchlorate, C29H50Cl2N4NiO8
  57. Crystal structure of (Z)-6-(dimethylamino)-3,3-bis(4-(dimethylamino)phenyl)-2-(2-(quinoxalin-2-ylmethylene)hydrazinyl)-2,3-dihydroinden-1-one, C35H35N7O
  58. 5-Methyl-N′-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carbonyl]-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carbohydrazide, C22H22N8O2
  59. Crystal structure of 2,3-dichloro-6-methoxyquinoxaline, C9H6Cl2N2O
  60. Synthesis and crystal structure of 7-chloro-2-(ethylsulfinyl)-6-fluoro-3-(1H-pyrazole-1-yl)-4H-thiochromen-4-one, C13H10FN3OS2
  61. Crystal structure of 4-ethylpiperazine-1-carbothioic dithioperoxyanhydride, C14H26N4S4
  62. Crystal structure of 2-(2-(6-methylpyridin-2-yl)naphthalen-1-yl)pyrimidine, C20H15N3
  63. The crystal structure of N′-((1E,2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-ylidene)-3-methylbenzohydrazide, C23H22N2O4
  64. Crystal structure of catena-poly[(μ2-isophthalato-κ2O:O′)-(2,5-di(pyrazin-2-yl)-4,4′-bipyridine-κ3N,N′,N′′)zinc(II)] — water (2/5), C26H21N6O6.5Zn
  65. Crystal structure of (3E,5E)-3,5-bis(3-nitrobenzylidene)-1-((4-(trifluoromethyl)phenyl)sulfonyl)piperidin-4-one — dichloromethane (2/1), C53H38Cl2F6N6O14S2
  66. Crystal structure of (μ2-oxido)-bis(N,N′-o-phenylenebis(salicylideneiminato))diiron(III) — N,N′-dimethylformamide, C47H43Fe2N4O9
  67. Crystal structure of N1,N3-bis(2-hydroxyethyl)-N1, N1,N3,N3-tetramethylpropane-1,3-diaminium dibromide, C11H28Br2N2O2
  68. Crystal structure of (E)-N-(4-chlorophenyl)-1-(pyridin-2-yl)methanimine, C12H9ClN2
  69. Crystal structure of 8-bromo-6-oxo-2-phenyl-6H-pyrrolo[3,2,1-ij]quinoline-5-carbaldehyde, C18H11BrNO2
  70. Crystal structure of 1,4-bis(2-azidoethyl)piperazine-1,4-diium dichloride trihydrate, C8H18N8Cl2 ⋅ 3 H2O
  71. Crystal structure of (E)-4-bromo-N-(pyridin-2-ylmethylene)aniline, C12H9BrN2
  72. Crystal structure of bis[(2-(3-bromophenyl)-5-methyl-1,3-dioxane-5-carboxylato-κ-O)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II), C40H60Br2N4NiO8
  73. The crystal structure of (1E,2E)-2-methyl-4-((7-oxo-7H-furo[3,2-g]chromen-9-yl)oxy)but-2-enal O-isonicotinoyl oxime–trichloromethane (3/1), C67H49Cl3N6O18
  74. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-methyl-1H-imidazol-3-ium hexafluoridophosphate(V), C8H13F6N2O2P
  75. Crystal structure of bis[(2-(2-bromophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κO)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II) hemihydrate C42H65Br2N4NiO8.5
  76. The crystal structure of N-(7-(4-fluorobenzylidene)-3-(4-fluorophenyl)-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbonothioyl)benzamide, C28H23F2N3OS
  77. The crystal structure of N1,N4-bis(pyridin-3-yl)cyclohexane-1,4-dicarboxamide, C18H20N4O2
  78. Crystal structure of (E)-2-(3,6-bis(ethylamino)-2,7-dimethyl-9H-xanthen-9-yl)-N′-((6-methylpyridin-2-yl)methylene)benzohydrazide – methanol (1/1), C34H37N5O3
  79. Crystal structure of 2-oxo-1-(pyrimidin-5-ylmethyl)-3-(3-(trifluoromethyl)phenyl)-1,2-dihydro-5l4-pyrido[1,2-a]pyrimidin-4-olate, C20H13F3N4O2
  80. Crystal structure of poly[(μ3-9H-carbazole-3,6-dicarboxylato-κ3O1: O2: O3)(μ2-4-(pyridin-4-yl)pyridine-κ2N1:N1′)zinc(II)], C19H11N2O4Zn
  81. Crystal structure of (E)-N′-((1,8-dihydropyren-1-yl)-methylene)picolinohydrazide, C23H15N3O
  82. Crystal structure of catena-poly{[μ2-1,2-bis(diphenylphosphino)ethane]dichloridocadmium(II)}, C26H24CdCl2P2
  83. Crystal structure of the 1:2 co-crystal between N,N′-bis(4-pyridylmethyl)oxalamide and acetic acid as a dihydrate, C14H14N4O2⋅2 C2H4O2⋅2 H2O
  84. Crystal structure of the co-crystal N,N′-bis(3-pyridylmethyl)oxalamide acetic acid (1/2), C14H14N4O2⋅2C2H4O2
  85. Crystal structure of the co-crystal N,N′-bis(4-pyridylmethyl)oxalamide and 2,3,5,6-tetrafluoro-1,4-di-iodobenzene (1/1), C14H14N4O2⋅C6F4I2
  86. Crystal structure of the co-crystal 4-[(4-carboxyphenyl)disulfanyl]benzoic acid–(1E,4E)-1-N,4-N-bis(pyridin-4-ylmethylidene)cyclohexane-1,4-diamine (1/1), C14H10O4S2⋅C18H20N4
  87. Crystal structure of hexacarbonyl-bis(μ2-di-n-propyldithiocarbamato-κ3S,S′:S;κ3S:S:S′)-di-rhenium(I), C20H28N2O6Re2S4
  88. Crystal structure of fac-tricarbonyl-morpholine-κN-(morpholinocarbamodithioato-κ2S,S′)rhenium(I), C12H17N2O5ReS2
https://doi.org/10.1515/ncrs-2019-0086
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Artikel in diesem Heft

  1. Frontmatter
  2. Crystal structure of poly[diaqua-(μ8-1,1′:2′,1′′-terphenyl-3,3′′,4′,5′-tetracarboxylato-κ8O1:O2:O3:O4:O5:O6:O7:O8)dicopper(II)], C22H14Cu2O10
  3. Crystal structure of 2-((1H-benzo[d]imidazol-2-ylimino)methyl)-4,6-di-tert-butylphenol, C22H27N3O
  4. Crystal structure of (4-ethoxynaphthalen-1-yl)(furan-2-yl)methanone, C17H14O3
  5. Crystal structure of 1-nonylpyridazin-1-ium iodide, C13H23N2I
  6. Crystal structure of bis[diaqua(1,10-phenanthroline-κ2N, N′)-copper(II)]diphenylphosphopentamolybdate dihydrate, C36H38Cu2Mo5N4O27P2
  7. The crystal structure of tetrakis(imidazole)-copper(I) hexafluorophosphate, C12H16CuF6PN8
  8. The crystal structure of dimethyl ((3,5-di-tert-butyl-4-hydroxyphenyl)(phenyl)methyl)phosphonate, C23H33O4P
  9. Crystal structure of diaqua-bis(1,10-phenanthroline κ2N,N′)nickel(II) trifluoroacetate- trifluoroacetic acid (1/1), C30H21F9N4NiO8
  10. Crystal structure of 2-(naphthalen-2-yl)-1,8-naphthyridine, C18H12N2
  11. Synthesis and crystal structure of a new polymorph of diisopropylammonium trichloroacetate, C8H16Cl3NO2
  12. Crystal structure of dimethanol-bis(1-((2-methyl-1H-benzo[d]imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κN)-bis(thiocyanato-κN)cadmium(II) C34H34CdN12O2S2
  13. Crystal structure of ethyl 2,2-difluoro-2-(7-methoxy-2-oxo-2H-chromen-3-yl)acetate, C14H12F2O5
  14. The crystal structure of bis[μ2-(N,N-diethylcarbamodithioato-κS:κS,κS′)] bis[1′-(diphenylphosphino-κP)-1-cyanoferrocene]disilver(I), C56H56Ag2Fe2N4P2S4
  15. Crystal structure of bis(di-n-butylammonium) tetrachloridodiphenylstannate(IV), C28H50Cl4N2Sn
  16. The crystal structure of poly[(μ5-2-((5-bromo-3-formyl-2-hydroxybenzylidene)amino)benzenesulfonato-κ6O:O:O,O′:O′:O′′)sodium(I)], C13H9O4NSBrNa
  17. Crystal structure of catena-{poly[bis(O,O′-diethyldithiophosphato-S)-(μ2-1,2-bis(4-pyridylmethylene)hydrazine-N,N′)-zinc(II)] di-acetonitrile solvate}, {C20H30N4O4P2S4Zn ⋅ 2 C2H3N}n
  18. Halogen and hydrogen bonding in the layered crystal structure of 2-iodoanilinium triiodide, C6H7I4N
  19. Crystal structure of cyclohexane-1,4-diammonium 2-[(2-carboxylatophenyl)disulfanyl]benzoate — dimethylformamide — monohydrate (1/1/1), [C6H16N2][C14H8O4S2] ⋅ C3H7NO⋅H2O
  20. The synthesis and crystal structure of isobutyl 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C16H13Cl2F6N3O3S
  21. Isolation and crystal structure of bufotalinin — methanol (1/1), C25H34O7
  22. Crystal structure of benzylbis(1,3-diphenylpropane-1,3-dionato-κ2O,O′) chloridotin(IV), C37H29ClO4Sn
  23. Crystal structure of Bis{1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-methyl-imidazol)}diiodidocadmium(II), [Cd(C11H11N5)2I2], C22H22N10I2Cd
  24. Crystal structure of 4-isobutoxybenzaldehyde oxime, C11H15NO2
  25. The crystal structure of bis(acetato-κ1O)-bis(N′-hydroxypyrimidine-2-carboximidamide-κ2N,N′)manganese(II) — methanol (1/2), C14H18MnN8O6, 2(CH3OH)′
  26. Crystal structure of poly[bis(μ2-bis(4-(1H-imidazol-1-yl)phenyl)amine-κ2N:N′)-bis(nitrato-κO)cadmium(II)], C36H30CdN12O6
  27. Crystal structure and optical properties of 1,6-bis(methylthio)pyrene, C18H14S2
  28. The crystal structure of hexaquamagnesium(II) bis(3,4-dinitropyrazol-1-ide), C6H14MgN8O14
  29. Halogen bonds in the crystal structure of 4,3:5,4-terpyridine – 1,4-diiodotetrafluorobenzene (1/1), C21H11F4I2N3
  30. Crystal structure and photochromic properties of a novel photochromic perfluordiarylethene containing a triazole bridged pyridine group moiety, C24H18F6N4S2
  31. Crystal structure of bis[(μ3-oxido)-(μ2-(N,N-diisopropylthiocarbamoylthio) acetato-κ2O,O′)-((N,N-diisopropylthiocarbamoylthio)acetato-κO)-bis(di-4-methylbenzyl-tin(IV))], C100H136N4O10S8Sn4
  32. Crystal structure of dibromidobis(4-bromobenzyl)tin(IV), C14H12Br4Sn
  33. The crystal structure of (4Z)-2-[(E)-(1-ethyl-3,3-dimethyl-1,3-dihydro-2H-indol-2-ylidene)methyl]-4-[(1-ethyl-3,3-dimethyl-3H-indolium-2-yl)methylidene]-3-oxocyclobut-1-en-1-olate, C30H32N2O2
  34. The crystal structure of (E)-3-(4-(dimethylamino)styryl)-5,5-dimethylcyclohex-2-en-1-one, C18H23NO
  35. Crystal structure of dihydrazinium 1H-pyrazole-3,5-dicarboxylate, C5H12N6O4
  36. Crystal structure of poly[μ2-1,4-bis((1H-imidazol-1-yl)methyl)benzene-κ2N:N′)-(μ2-4-sulfidobenzoate-κ2O:S)cobalt(II)] dihydrate, C42H44Co2N8O7S2
  37. Crystal structure of 8-(3,4-dimethylbenzylidene)-6,10-dioxaspiro[4.5]decane-7,9-dione, C17H18O4
  38. Crystal structure of 4-(2-bromo-4-(6-morpholino-3-phenyl-3H-benzo[f]chromen-3-yl) cyclohexa-2,5-dien-1-yl)morpholine, C33H31BrN2O
  39. Synthesis and crystal structure of 2-((1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-4-yl)methylene)-2,3-dihydro-1H-inden-1-one, C23H16N2OS
  40. Crystal structure of poly[(μ2-1,1′-(oxybis(4,1-phenylene)bis(1H-imidazole)-κ2N,N′)(μ2-1,3-benzenecarboxylato-κ3O,O′:O′′)zinc(II)] dihydrate, C26H22N4O7Zn
  41. Crystal structure of diaqua-bis(cinnamato-κ2O,O′)zinc(II), C18H18ZnO6
  42. Crystal structure of 2-(prop-2-yn-1-yloxy)-1-naphthaldehyde, C14H10O2
  43. Crystal structure and photochromic properties of 1-(2-methyl-5-phenyl-3-thienyl)-2-{2-methyl-5-[4-(9-fluorenone hydrazone)-phenyl]-3-thienyl}perfluorocyclopentene, C41H26F6N2S2
  44. Hydrothermal synthesis and crystal structure of cylo[tetraaqua-bis(μ2-1,4-bis(1H-benzo[d]imidazol-1-yl)but-2-ene-κ2N:N′)-bis(μ2-4-nitro-phthalate-κ2O,O′)dinickel(II)], C26H23N5O8Ni
  45. Crystal structure of 3-[methyl(phenyl)amino]-1-phenylthiourea, C14H15N3S
  46. Crystal structure of 1-(4-chlorophenyl)-3-[methyl(phenyl)amino]thiourea, C14H14ClN3S
  47. Crystal structure of 2-tert-butyl-1H-imidazo[4,5-b]pyridine, C10H13N3
  48. Crystal structure of 5-carboxy-2-(2-carboxyphenyl)-1H-imidazol-3-ium-4-carboxylate dihydrate, C12H8N2O6⋅2(H2O)
  49. The crystal structure of dichlorido-μ2-dichlorido-(η2-1,4-bis(4-vinylbenzyl)-1,4-diazabicyclo[2.2.2]octane-1,4-diium)dicopper(I), C24H30N2Cu2Cl4
  50. Crystal structure of 4-bromobenzyl (Z)-N-(adamantan-1-yl)morpholine-4-carbothioimidate, C22H29BrN2OS
  51. Crystal structure of (4S,4aS,6aR,6bR,12aS,12bR,14aS,14bR)-3,3,6a,6b,9,9,12a-heptamethyloctadecahydro-1H,3H-4,14b-ethanophenanthro[1,2-h]isochromene-1(6bH)-one, C30H48O2
  52. Crystal structure of 3,5-bis(trifluoromethyl)benzyl (Z)-N′-(adamantan-1-yl)-4-phenylpiperazine-1-carbothioimidate, C30H33F6N3S
  53. The crystal structure of 3-methoxyphenanthridin-6(5H)-one, C14H11NO2
  54. Crystal structure of 4-(5,5-difluoro-1,3,7,9-tetramethyl-3H,5H-5λ4-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinin-10-yl)pyridin-1-ium tetraiodidoferrate(III), C18H19BF2FeI4N3
  55. Crystal structure of 2-(3-methoxyphenyl)-3-((phenylsulfonyl)methyl)imidazo[1,2-a]pyridine, C21H18N2O3S
  56. Crystal structure of [(2-(2-chlorophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κ2O,O′) (5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II) perchlorate, C29H50Cl2N4NiO8
  57. Crystal structure of (Z)-6-(dimethylamino)-3,3-bis(4-(dimethylamino)phenyl)-2-(2-(quinoxalin-2-ylmethylene)hydrazinyl)-2,3-dihydroinden-1-one, C35H35N7O
  58. 5-Methyl-N′-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carbonyl]-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carbohydrazide, C22H22N8O2
  59. Crystal structure of 2,3-dichloro-6-methoxyquinoxaline, C9H6Cl2N2O
  60. Synthesis and crystal structure of 7-chloro-2-(ethylsulfinyl)-6-fluoro-3-(1H-pyrazole-1-yl)-4H-thiochromen-4-one, C13H10FN3OS2
  61. Crystal structure of 4-ethylpiperazine-1-carbothioic dithioperoxyanhydride, C14H26N4S4
  62. Crystal structure of 2-(2-(6-methylpyridin-2-yl)naphthalen-1-yl)pyrimidine, C20H15N3
  63. The crystal structure of N′-((1E,2E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-ylidene)-3-methylbenzohydrazide, C23H22N2O4
  64. Crystal structure of catena-poly[(μ2-isophthalato-κ2O:O′)-(2,5-di(pyrazin-2-yl)-4,4′-bipyridine-κ3N,N′,N′′)zinc(II)] — water (2/5), C26H21N6O6.5Zn
  65. Crystal structure of (3E,5E)-3,5-bis(3-nitrobenzylidene)-1-((4-(trifluoromethyl)phenyl)sulfonyl)piperidin-4-one — dichloromethane (2/1), C53H38Cl2F6N6O14S2
  66. Crystal structure of (μ2-oxido)-bis(N,N′-o-phenylenebis(salicylideneiminato))diiron(III) — N,N′-dimethylformamide, C47H43Fe2N4O9
  67. Crystal structure of N1,N3-bis(2-hydroxyethyl)-N1, N1,N3,N3-tetramethylpropane-1,3-diaminium dibromide, C11H28Br2N2O2
  68. Crystal structure of (E)-N-(4-chlorophenyl)-1-(pyridin-2-yl)methanimine, C12H9ClN2
  69. Crystal structure of 8-bromo-6-oxo-2-phenyl-6H-pyrrolo[3,2,1-ij]quinoline-5-carbaldehyde, C18H11BrNO2
  70. Crystal structure of 1,4-bis(2-azidoethyl)piperazine-1,4-diium dichloride trihydrate, C8H18N8Cl2 ⋅ 3 H2O
  71. Crystal structure of (E)-4-bromo-N-(pyridin-2-ylmethylene)aniline, C12H9BrN2
  72. Crystal structure of bis[(2-(3-bromophenyl)-5-methyl-1,3-dioxane-5-carboxylato-κ-O)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II), C40H60Br2N4NiO8
  73. The crystal structure of (1E,2E)-2-methyl-4-((7-oxo-7H-furo[3,2-g]chromen-9-yl)oxy)but-2-enal O-isonicotinoyl oxime–trichloromethane (3/1), C67H49Cl3N6O18
  74. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-methyl-1H-imidazol-3-ium hexafluoridophosphate(V), C8H13F6N2O2P
  75. Crystal structure of bis[(2-(2-bromophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κO)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II) hemihydrate C42H65Br2N4NiO8.5
  76. The crystal structure of N-(7-(4-fluorobenzylidene)-3-(4-fluorophenyl)-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbonothioyl)benzamide, C28H23F2N3OS
  77. The crystal structure of N1,N4-bis(pyridin-3-yl)cyclohexane-1,4-dicarboxamide, C18H20N4O2
  78. Crystal structure of (E)-2-(3,6-bis(ethylamino)-2,7-dimethyl-9H-xanthen-9-yl)-N′-((6-methylpyridin-2-yl)methylene)benzohydrazide – methanol (1/1), C34H37N5O3
  79. Crystal structure of 2-oxo-1-(pyrimidin-5-ylmethyl)-3-(3-(trifluoromethyl)phenyl)-1,2-dihydro-5l4-pyrido[1,2-a]pyrimidin-4-olate, C20H13F3N4O2
  80. Crystal structure of poly[(μ3-9H-carbazole-3,6-dicarboxylato-κ3O1: O2: O3)(μ2-4-(pyridin-4-yl)pyridine-κ2N1:N1′)zinc(II)], C19H11N2O4Zn
  81. Crystal structure of (E)-N′-((1,8-dihydropyren-1-yl)-methylene)picolinohydrazide, C23H15N3O
  82. Crystal structure of catena-poly{[μ2-1,2-bis(diphenylphosphino)ethane]dichloridocadmium(II)}, C26H24CdCl2P2
  83. Crystal structure of the 1:2 co-crystal between N,N′-bis(4-pyridylmethyl)oxalamide and acetic acid as a dihydrate, C14H14N4O2⋅2 C2H4O2⋅2 H2O
  84. Crystal structure of the co-crystal N,N′-bis(3-pyridylmethyl)oxalamide acetic acid (1/2), C14H14N4O2⋅2C2H4O2
  85. Crystal structure of the co-crystal N,N′-bis(4-pyridylmethyl)oxalamide and 2,3,5,6-tetrafluoro-1,4-di-iodobenzene (1/1), C14H14N4O2⋅C6F4I2
  86. Crystal structure of the co-crystal 4-[(4-carboxyphenyl)disulfanyl]benzoic acid–(1E,4E)-1-N,4-N-bis(pyridin-4-ylmethylidene)cyclohexane-1,4-diamine (1/1), C14H10O4S2⋅C18H20N4
  87. Crystal structure of hexacarbonyl-bis(μ2-di-n-propyldithiocarbamato-κ3S,S′:S;κ3S:S:S′)-di-rhenium(I), C20H28N2O6Re2S4
  88. Crystal structure of fac-tricarbonyl-morpholine-κN-(morpholinocarbamodithioato-κ2S,S′)rhenium(I), C12H17N2O5ReS2
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