Home Crystal structure of cyclohexane-1,4-diammonium 2-[(2-carboxylatophenyl)disulfanyl]benzoate — dimethylformamide — monohydrate (1/1/1), [C6H16N2][C14H8O4S2] ⋅ C3H7NO⋅H2O
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Crystal structure of cyclohexane-1,4-diammonium 2-[(2-carboxylatophenyl)disulfanyl]benzoate — dimethylformamide — monohydrate (1/1/1), [C6H16N2][C14H8O4S2] ⋅ C3H7NO⋅H2O

  • Sang Loon Tan and Edward R.T. Tiekink ORCID logo EMAIL logo
Published/Copyright: May 22, 2019
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 234 Issue 5

Abstract

[C6H16N2][C14H8O4S2]⋅C3H7NO⋅H2O, triclinic, P1̄ (no. 2), a = 7.86120(10) Å, b = 12.2464(2) Å, c = 14.1615(2) Å, α = 111.293(1)°, β = 105.767(2)°, γ = 93.690(1)°, V = 1202.11(3) Å3, Z = 2, Rgt(F) = 0.0373, wRref(F2) = 0.1054, T = 100(2) K.

CCDC no.: 1904095

The asymmetric unit of the title crystal structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Yellow prism
Size:0.10 × 0.07 × 0.02 mm
Wavelength:Cu Kα radiation (1.54184 Å)
μ:2.39 mm−1
Diffractometer, scan mode:XtaLAB Synergy, ω
θmax, completeness:76.6°, >99%
N(hkl)measured, N(hkl)unique, Rint:30359, 5016, 0.034
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4635
N(param)refined:333
Programs:CrysAlisPRO [1], SHELX [2], [3], WinGX/ORTEP [4]
Table 2:

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

AtomxyzUiso*/Ueq
S10.47247(5)−0.09550(3)0.75674(3)0.01450(11)
S20.46421(5)0.06994(3)0.75039(3)0.01334(11)
O10.73605(16)−0.39304(11)0.72755(10)0.0184(3)
O20.50258(19)−0.31583(12)0.76985(11)0.0249(3)
O30.19676(17)0.37981(11)0.76832(10)0.0200(3)
O40.44096(15)0.29557(10)0.78509(9)0.0160(2)
C10.5042(2)−0.18708(14)0.63395(13)0.0126(3)
C20.5723(2)−0.29253(14)0.62601(13)0.0130(3)
C30.5971(2)−0.36196(14)0.52982(13)0.0137(3)
H30.646027−0.4321200.5243400.016*
C40.5526(2)−0.33193(14)0.44177(13)0.0146(3)
H40.568503−0.3817030.3766140.018*
C50.4844(2)−0.22786(15)0.45021(13)0.0144(3)
H50.453322−0.2061100.3906170.017*
C60.4618(2)−0.15587(14)0.54600(13)0.0133(3)
H60.416767−0.0843830.5516510.016*
C70.6073(2)−0.33633(14)0.71590(13)0.0151(3)
C80.2286(2)0.06397(14)0.69131(13)0.0122(3)
C90.1568(2)0.16901(14)0.70518(12)0.0122(3)
C10−0.0295(2)0.15931(15)0.66802(13)0.0150(3)
H10−0.0794080.2298460.6794650.018*
C11−0.1436(2)0.04968(16)0.61496(14)0.0168(3)
H11−0.2701840.0452570.5927970.020*
C12−0.0713(2)−0.05358(15)0.59448(14)0.0170(3)
H12−0.147843−0.1291760.5544360.020*
C130.1133(2)−0.04625(14)0.63262(14)0.0157(3)
H130.161982−0.1173330.6186010.019*
C140.2723(2)0.29144(14)0.75705(12)0.0128(3)
N10.0944(2)0.56987(13)0.72609(12)0.0195(3)
H1N−0.0130(18)0.584(2)0.7277(18)0.023*
H2N0.128(3)0.5145(16)0.7493(18)0.023*
H3N0.178(2)0.6346(14)0.7635(16)0.023*
C150.0930(2)0.52648(14)0.61238(13)0.0141(3)
H150.2125340.5048180.6095760.017*
C16−0.0516(2)0.41505(14)0.54447(13)0.0150(3)
H16A−0.1689260.4326390.5531020.018*
H16B−0.0219430.3506740.5693110.018*
C170.0654(2)0.62665(14)0.57342(13)0.0145(3)
H17A0.1673210.6940920.6165910.017*
H17B−0.0459800.6552620.5834490.017*
N20.65562(18)0.52327(12)0.88085(11)0.0141(3)
H4N0.578(2)0.4563(12)0.8439(15)0.017*
H5N0.597(3)0.5768(15)0.9131(16)0.017*
H6N0.691(3)0.5457(18)0.8353(14)0.017*
C180.8100(2)0.50552(14)0.95961(13)0.0129(3)
H180.7642590.4869331.0124220.015*
C190.8883(2)0.40004(14)0.90183(13)0.0144(3)
H19A0.9275100.4148660.8460820.017*
H19B0.7945570.3271980.8662820.017*
C200.9514(2)0.61912(14)1.01969(13)0.0144(3)
H20A0.8981180.6848281.0591890.017*
H20B0.9926850.6418630.9681480.017*
O50.2162(2)0.78571(13)0.91767(12)0.0323(3)
N30.1420(2)0.96296(15)0.91935(14)0.0275(4)
C210.2513(3)0.89438(19)0.95340(17)0.0290(4)
H210.3621290.9333091.0085230.035*
C22−0.0258(3)0.9061(2)0.83582(19)0.0397(5)
H22A−0.0127430.9004790.7674060.060*
H22B−0.1187100.9530600.8509920.060*
H22C−0.0604250.8259290.8320380.060*
C230.2029(4)1.0896(2)0.9614(2)0.0422(6)
H23A0.3144061.1122841.0214750.063*
H23B0.1107591.1309910.9861010.063*
H23C0.2251221.1117920.9053740.063*
O1W0.48304(19)0.68124(12)0.00114(11)0.0255(3)
H1W0.404(3)0.716(2)−0.022(2)0.038*
H2W0.490(4)0.699(2)0.0654(10)0.038*

Source of material

The title co-crystal salt was prepared through the solvent drop-assisted grinding of 2-mercaptobenzoic acid (2-MBA; Merck) and N,N-bis((pyridine-4-yl)methylene)-cyclohexane-1,4-diamine (4-PMCD) in a 1:1 molar ratio (0.001 mol, 0.154 g for 2-MBA and 0.001 mol, 0.292 g 4-PMCD). The former was used as received without purification, while the latter was prepared according to the literature procedure [5], M. pt. (Hanon MP-450); 480.7−481.4 K; lit. [5]: 481−482 K. The mixture was ground for 15 min in the presence of a few drops of methanol that lead to a yellow slurry. This was dissolved in dimethylformamide (2 mL) and carefully layered with the same volume of benzene. Yellow crystals were obtained approximately 1 week after the experiment. M. pt.: 441.5−443.9 K. IR (Bruker Vertex 70v; cm−1): 3357−3275(w) ν(NH), 3048−2866(w) ν(CH), 1692(m) ν(C=O), 1584−1447(s) ν(C=C), 1367(s) ν(C—N), 735(s) ν(C=C).

Experimental details

The C-bound H atoms were geometrically placed (C—H = 0.95−1.00 Å) and refined as riding with Uiso(H) = 1.2−1.5Ueq(C). The O- and N-bound H-atoms were located in difference Fourier maps but were refined with distance restraints of O—H = 0.84+−0.01 Å and N—H = 0.88+−0.01 Å, respectively, and with Uiso(H) set to 1.5Ueq(O) and 1.2Ueq(N). The maximum and minimum residual electron density peaks of 1.16 and 0.45 eÅ−3, respectively, were located 1.07 and 0.62 Å from the H22b and C23 atoms, respectively.

Comment

Recent co-crystallization studies involving isomeric Schiff bases appended with pyridyl donors, i.e. N,N′-bis((pyridine-n-yl)methylene)cyclohexane-1,4-diamines, for n = 2, 3 and 4, as coformers have resulted in the isolation of crystals whereby the original n = 2 species has been converted into a cyclohexane-1,4-diammonium di-cation, as in its salt with pyridine-2-carboxylate [6]. In another experiment, the n = 2 species was converted to a 2-(4-ammoniocyclohexyl)-3-(pyridin-2-yl)imidazo[1,5-a]pyridin-2-ylium dication in a salt with 2-[(2-carboxylatophenyl)disulfanyl]benzoate [7]. These experiments are doubly complicated as the isomeric n-mercaptobenzoic acids employed are also known to be susceptible to side reactions in co-crystallization experiments [8], [9]. In another example of an unexpected outcome of a co-crystallization experiment with these molecules, the title salt solvate hydrate was isolated from the 1:1 co-crystallization of (4-py)—CH=NC6H10N=CH—(4-py) and 2-mercaptobenzoic acid.

X-ray crystallography shows the product to comprise two independent cyclohexane-1,4-diammonium dications, each located about a centre of inversion, a 2-[(2-carboxylatophenyl)disulfanyl]benzoate di-anion, and a molecule each of dimethylformamide (DMF) and water (figure, 70% probability displacement ellipsoids with unlabelled atoms related by the symmetry operations i: − x, 1 – y, 1 – z and ii: 2 – x, 1 – y, 2 – z). The cation/anion assignments are readily confirmed based on the pattern of hydrogen bonding in the crystal (see below) and in the near equivalence of the C7—O1, O2 [1.271(2), 1.247(2) Å] and C14—O3, O4 [1.248(2), 1.269(2) Å] bond lengths. Each dication adopts a crystallographically imposed chair conformation so that the 1,4-ammonium groups are anti, typical for this cation [10]. The dianion is twisted as seen in the C1—S1—S2—C2 torsion angle of 91.42(8)°, and in the dihedral angle of 79.32(8)° formed between the two phenyl rings. The O1-carboxylate group is twisted significantly out of the plane of the phenyl ring to which it is bound as seen in C1—C2—C7—O1 torsion angle of −148.22(16)° and dihedral angle of 35.77(9)° between these residues. A significantly more co-planar relationship is evident for the O3-carboxylate with the C8—C9—C14—O3 torsion angle being −178.31(15)° and the dihedral angle being 4.84(13)°.

Significant hydrogen bonding occurs in the crystal, most being charge-assisted, which results in the stabilization of a three-dimensional architecture. The N1-dication forms donor interactions to carboxylate-O1 and O3 atoms as well as to the DMF-O5 atom [N1—H1n⋯O1iii: H1n⋯O1iii = 2.010(16) Å, N1⋯O1iii = 2.887(2) Å with angle at H1n = 177(3)°; N1—H2n⋯O3: H2n⋯O3 = 1.86(2) Å, N1⋯O3 = 2.723(2) Å and angle = 168(2)°; N1—H3n⋯O5: H3n⋯O5 = 2.22(2) Å, N1n⋯O5 = 2.884(2) Å and angle = 132.0(15)° for symmetry operation iii: −1 + x, 1 + y, z]. A similar pattern occurs for the N2-dication but, the third hydrogen bond is oriented to the water molecule [N2—H4n⋯O4: H4n⋯O4 = 1.944(17) Å, N2⋯O4 = 2.805(2) Å with angle at H4n = 166.9(16)°; N2—H5n⋯O1wiv: H5n⋯O1wiv = 1.90(2) Å, N2⋯O1wiv = 2.772(2) Å with angle = 170.0(19)°; N2—H6n⋯O1v: H6n⋯O1v = 2.03(2) Å, N2⋯O1v = 2.906(2) Å with angle = 171(2)°; for symmetry operations iv: x, y, 1 + z and v: x, 1 + y, z]. The water molecule forms donor interactions to carboxylate-O4 and DMF-O5 atoms [O1w—H1w⋯O5vi: H1w⋯O5vi = 1.91(3) Å, O1w⋯O5vi = 2.744(2) Å with angle at H1w = 176(3)°; O1w—H2w⋯O4vii: H2w⋯O4vii = 2.013(15) Å, O1w⋯O4vii = 2.8237(18) Å with angle = 162(3)° for symmetry operations vi: x, y, −1 + z and vii: 1 – x, 1 – y, 1 – z]. In this scheme, there is no role for the carboxylate-O2 atom. However, it is noted that this atom accepts two weak hydrogen bonds from ammonium-N1 and N3 groups [N1—H3n⋯O2v: H3n⋯O2v = 2.554(17) Å, N1⋯O2v = 3.217(2) Å with angle at H3n = 132.5(15)°; N2—H6n⋯O2v: H6n⋯O2v = 2.58(2) Å, N2⋯O2v = 3.054(2) Å with angle = 114.5(18)°].

Funding source: crystal engineering studies

Award Identifier / Grant number: INT-FST-RCCM-2016–01

Funding statement: Sunway University is thanked for support of crystal engineering studies (Grant No. INT-FST-RCCM-2016–01).

References

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Received: 2019-02-20
Accepted: 2019-03-19
Published Online: 2019-05-22
Published in Print: 2019-09-25

©2019 Sang Loon Tan et al., published by De Gruyter, Berlin/Boston

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

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  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-2019-0131
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Articles in the same Issue

  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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