Home Crystal structure of 2-({[5-(adamantan-2-yl)-2-sulfanylidene-1,3,4-oxadiazolidin-3-yl]methyl}amino)benzonitrile, C20H22N4OS
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Crystal structure of 2-({[5-(adamantan-2-yl)-2-sulfanylidene-1,3,4-oxadiazolidin-3-yl]methyl}amino)benzonitrile, C20H22N4OS

  • Lamya H. Al-Wahaibi , Olivier Blacque , Nora H. Al-Shaalan , Edward R. T. Tiekink and Ali A. El-Emam ORCID logo EMAIL logo
Published/Copyright: December 19, 2022
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 2

Abstract

C20H22N4OS, triclinic, P 1 ‾ (no. 2), a = 6.8528(3) Å, b = 11.3498(5) Å, c = 13.3896(9) Å, α = 114.083(5)°, β = 104.326(4)°, γ = 90.369(3)°, V = 914.38(9) Å3, Z = 2, R gt (F) = 0.0844, wR ref (F2) = 0.2217, T = 160 K.

CCDC no.: 2216322

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 plate
Size: 0.19 × 0.10 × 0.02 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 1.70 mm−1
Diffractometer, scan mode: XtaLAB Synergy, ω
θmax, completeness: 74.6°, >99%
N(hkl)measured, N(hkl)unique, Rint: 24,423, 24,423
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 19,275
N(param)refined: 239
Programs: CrysAlisPRO [1], Shelx [2, 3], Olex2 [4]
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.3603 (6) 0.8333 (3) 0.6742 (3) 0.0283 (8)
C2 0.5068 (6) 0.7458 (3) 0.6457 (3) 0.0278 (8)
C3 0.5088 (7) 0.6359 (4) 0.6694 (4) 0.0350 (10)
H3 0.410156 0.619318 0.702435 0.042*
C4 0.6509 (8) 0.5528 (4) 0.6455 (4) 0.0372 (10)
H4 0.652854 0.479596 0.662962 0.045*
C5 0.7932 (7) 0.5761 (3) 0.5951 (4) 0.0340 (9)
H5 0.892182 0.518273 0.578294 0.041*
C6 0.7923 (6) 0.6827 (3) 0.5691 (3) 0.0292 (8)
H6 0.888634 0.696007 0.533294 0.035*
C7 0.6515 (6) 0.7703 (3) 0.5950 (3) 0.0248 (8)
C8 0.7895 (6) 0.9163 (3) 0.5261 (3) 0.0254 (8)
H8A 0.925414 0.896205 0.556915 0.031*
H8B 0.798008 1.011363 0.549199 0.031*
C9 0.8366 (6) 0.7691 (3) 0.3337 (3) 0.0233 (8)
C10 0.5462 (6) 0.7960 (3) 0.2346 (3) 0.0243 (8)
C11 0.3895 (6) 0.7742 (3) 0.1280 (3) 0.0235 (7)
C12 0.3016 (6) 0.6287 (3) 0.0660 (3) 0.0263 (8)
H12A 0.412221 0.574220 0.050279 0.032*
H12B 0.237979 0.604900 0.115127 0.032*
C13 0.1439 (6) 0.6038 (3) −0.0454 (3) 0.0293 (8)
H13 0.088109 0.509684 −0.085046 0.035*
C14 0.2442 (7) 0.6392 (4) −0.1220 (3) 0.0322 (9)
H14A 0.355671 0.585673 −0.138316 0.039*
H14B 0.143235 0.621426 −0.195166 0.039*
C15 0.3283 (7) 0.7839 (4) −0.0614 (4) 0.0307 (9)
H15 0.392055 0.807313 −0.111492 0.037*
C16 0.4882 (6) 0.8091 (3) 0.0495 (3) 0.0272 (8)
H16A 0.546063 0.901778 0.088068 0.033*
H16B 0.599666 0.755638 0.033004 0.033*
C17 0.1557 (7) 0.8665 (4) −0.0363 (4) 0.0339 (9)
H17A 0.052801 0.850609 −0.108288 0.041*
H17B 0.209495 0.959864 0.001956 0.041*
C18 0.0579 (6) 0.8306 (4) 0.0408 (4) 0.0310 (9)
H18 −0.054954 0.884468 0.057081 0.037*
C19 0.2158 (6) 0.8569 (3) 0.1524 (3) 0.0267 (8)
H19A 0.152323 0.835019 0.202494 0.032*
H19B 0.269868 0.950240 0.191907 0.032*
C20 −0.0282 (6) 0.6860 (4) −0.0208 (4) 0.0321 (9)
H20A −0.094507 0.662140 0.027267 0.038*
H20B −0.131178 0.669578 −0.093000 0.038*
N1 0.2453 (6) 0.9064 (3) 0.6983 (3) 0.0366 (8)
N2 0.6479 (5) 0.8798 (3) 0.5738 (3) 0.0275 (7)
H2 0.566 (6) 0.934 (3) 0.598 (4) 0.031 (11)*
N3 0.7322 (5) 0.8487 (3) 0.4011 (3) 0.0233 (7)
N4 0.5488 (5) 0.8661 (3) 0.3387 (3) 0.0242 (7)
O1 0.7161 (4) 0.7336 (2) 0.2254 (2) 0.0262 (6)
S1 1.06010 (15) 0.71962 (8) 0.36407 (9) 0.0295 (3)

Source of material

2–Aminobenzonitrile (0.59 g, 5.0 mmol) and 37% formaldehyde solution (0.5 mL) were added to a solution of 5-(adamantan-1-yl)-1,3,4-oxadiazole-2(3H)-thione [5] (1.18 g, 0.5 mmol) in ethanol (10 mL). The mixture was stirred at room temperature for 2 h and allowed to stand overnight. The precipitated crude product was filtered, washed with water, dried and crystallized from aqueous ethanol to yield 1.37 g (75%) of the title compound as colourless plates. M.pt: 447–449 K (uncorrected). IR ν (cm−1): 3374 (NH), 3021 (aromatic CH), 2911, 2850 (aliphatic CH), 2210 (CN), 1266 (C–O–C). 1 H NMR (CDCl3, 250 MHz): δ 1.72 (q, 6H, adamantane–H), 1.96 (s, 6H, adamantane–H), 2.10 (s, 3H, adamantane–H), 5.50 (d, 2H, NCH2N), 5.77 (t, 1H, NH), 6.86 (t, 1H, Ar–H), 7.31 (d, 1H, Ar–H), 7.47–7.51 (m, 2H, Ar–H). 13 C NMR (CDCl3, 62.9 MHz): δ 27.41, 34.55, 36.03, 39.02 (adamantane–C), 56.94 (NCH2N), 97.77 (CN), 112.72, 117.13, 119.35, 132.94. 134.50, 147.06 (Ar–C), 168.66 (oxadiazole C5), 176.94 (C=S). EI–MS m/z (Rel. Int.): 366 (M+, 8), 236 (100), 176 (29), 135 (97), 131 (58), 102 (42). Suitable single crystals for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in ethanol:chloroform (1:1, v/v) held at room temperature.

Experimental details

The C-bound H atoms were geometrically placed (C–H = 0.95–1.00 Å) and refined as riding with U iso (H) = 1.2U eq (C). The N-bound H atom was located in a difference map and refined with N–H = 0.87 ± 0.01 Å. The crystal was refined as a two-component twin. The diffraction intensities were integrated according to a merohedral twin law: component two is rotated by 180° around [0.00 −0.00 1.00] in reciprocal space or [0.40 0.40 0.82] in direct space with respect to component one. The maximum and minimum residual electron density peaks of 1.29 and 0.29 e Å−3, respectively, were located 0.02 and 0.90 Å from the S1 and C8 atoms, respectively.

Comment

Adamantane derivatives have long been known for their diverse chemotherapeutic activities [6], [7], [8]. In addition, the 1,3,4-oxadiazole heterocycle represents an important scaffold in many chemotherapeutic agents [9, 10]. It was in this context that the title hybrid adamantanyl/oxadiazolidin-3-yl derivative, 1, was synthesised and its crystal and molecular structures studied.

The molecular structure of 1 is shown in the upper view of the figure (50% probability ellipsoids). The molecule is constructed about a strictly planar oxadiazolidin-3-yl ring appended at the N3 position by the methylene-bound substituent and at the C10 position by the adamantan-2-yl group. The substituted phenyl ring occupies a position almost perpendicular to the five-membered ring [dihedral angle = 72.2(2)°] so the molecule has the shape of the letter L. The amine–N–H and phenyl-nitrile groups project to the same side of the molecule as does the non-substituted ring-nitrogen atom. Within the five-membered ring, the short C10–N4 bond length [1.288(5) Å] as well as standard C9–N3 [1.343(5) Å] and C9, C10–O1 [1.368(5) & 1.373(5) Å] bond lengths are suggestive of limited delocalisation of π-electron density over ring.

There are five literature precedents for 1. Referring to the overlay diagram shown in the lower view of the figure, the molecule of 1 is shown in red; the molecules have been overlapped so the S, O and unsubstituted N atoms of the oxadiazolidin-3-yl fragment are coincident. The parent compound [11; aquamarine] and 4-fluorophenyl [12; pink], 4-chlorophenyl [13; yellow], 2-trifluoromethyl [14; black] and recently reported 4-trifluoromethyl [15; two independent molecules: green and blue] derivatives present very similar structural features with the exception of the relative orientations of the five- and six-membered rings. For example, the dihedral angle between the rings in the parent molecule, 2-trifluoromethyl derivative and 1 are 50.26(7), 66.80(6) and 72.2(2)°, respectively.

The most prominent intermolecular contact in the crystal of 1 is an amine–N–H…N(oxadiazolidin-3-yl) hydrogen bond [N2–H2…N4 i : H2…N4 i  = 2.30(4) Å, N2…N4 i  = 3.095(5) Å with angle at H2 = 156(4)° for symmetry operation (i): 1 − x, 2 − y, 1 − z] within a centrosymmetric aggregate and leading to a 10-membered synthon with the shape of an extended chair. The dimeric aggregates stack in columns along the a-axis with methylene–C–H…N(nitrile) [C8–H8a…N1 ii : H8a…N1 ii  = 2.48 Å, C8…N1 ii  = 3.426(6) Å with angle at H8a = 159° for (ii) 1 + x, y, z] and methylene–C–H…S(thione) [C8–H8b…S1 iii : H8b…S1 ii  = 2.85 Å, C8…S1 ii  = 3.813(4) Å with angle at H8b = 164° for (iii) 2 − x, 2 − y, 1 − z] contacts between them. Columns are connected into layers in the ab-plane by π(phenyl)…π(phenyl) [Cg(C2–C7)…Cg(C2–C7) iv  = 3.865(2) Å; slippage = 1.76 Å for (iv): 1 − x, 2 − y, 1 − z] contacts between centrosymmetrically related rings. The adamantan-2-yl groups project to either side of the supramolecular layer and inter-digitate along the c-axis with neighbouring layers.

Corresponding author: Ali A. El-Emam, Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt, E-mail:

Funding source: Deanship of Scientific Research at Princess Nourah bint Abdulrahman University through the Research Group Program

Award Identifier / Grant number: RGP-1442-0010-5

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: Deanship of Scientific Research at Princess Nourah bint Abdulrahman University through the Research Group Program (Grant No. RGP-1442-0010-5).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2022-11-02
Accepted: 2022-12-05
Published Online: 2022-12-19
Published in Print: 2023-04-25

© 2022 the author(s), published by De Gruyter, Berlin/Boston

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

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  49. The crystal structure of the cocrystal di-μ2-chlorido-tetramethyl-tetraphenyl-di-μ3-oxido-dichloridotetratin(IV) – diphenyl-methyl-chloridotin(IV)(1/2), C54H58Cl6O2Sn6
  50. Crystal structure of (3a7R,13bR)-3-((1R)-1-hydroxy-1-(5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-3a,11,11,13b-tetramethyl-2,3,3a,4,5,11,11a,12,13,13b-decahydroindeno[5′,4′:4,5] cyclohepta[1,2-c]oxepin-9(1H)-one, C30H40O5
  51. Crystal structure of 1-(4-methoxyphenyl)-2-phenoxyethan-1-one, C15H14O3
  52. Crystal structure of trans-tetrakis(3-phenylpyridine-κN)bis(thiocyanato-κN)nickel(II), C46H36N6NiS2
  53. Crystal structure of sodium catena-poly[bis(thiourea-κ1S)-tetrakis(μ2-thiourea-κ2S,S)tricopper(I)] difumarate, C14H29Cu3N12NaO8S6
  54. Crystal structure of bis(benzylamine-κ1N)-bis((E)-2-methyl-3-phenylacrylato-κ1O)copper(II), C34H36CuN2O4
  55. The crystal structure of 3,4-dihydroxybenzoic acid – 3-[7-{[2-(3,4-difluorophenyl)cyclopropyl]amino}-5-(propylsulfanyl)-3H-[1,2,3] triazolo[4,5-d]pyrimidin-3-yl]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol – water (1/1/1), C30H36F2N6O9S
  56. Crystal structure of catena-poly[dipyridine-bis(pyridine-2-carboxylato-κ 2 N,O)-bis(μ 2-pyridine-2-carboxylato-κ 2 N,O)-dinickel(II)], C34H26N6Ni2O8
  57. The crystal structure of 1-((1-methyl-1H-1,2,4-triazol-3-yl) methyl)-3-(2,4,5-trifluorobenzyl)-1,3,5-triazinane-2,4,6-trione, C14H11F3N6O3
  58. Crystal structure of (E)-2-((Z)-2-((1S,4R)-3,3-dimethylbicyclo[2.2.1] heptan-2-ylidene)ethylidene)hydrazine-1-carbothioamide, C24H38N6S2
  59. Crystal structure of photochromic 3-(5-(2,5-dimethylthiophen-3-yl)-2,2,3,3,4,4-hexafluorocyclopentyl)-2-methylbenzo[b]-thiophene, C20H14F6S2
  60. Crystal structure of bis(2,5,5,7-tetramethyl-1,4-diazepane-1,4-diium) diaqua-bis(1,2-diaminopropane)copper(II) bis(μ6-oxido)tetrakis(μ3-oxido)-tetradecakis(μ2-oxido)-octaoxido-decavanadium(V) – water (1/4), C24H76CuN8V10O34
  61. Crystal structure of 1,2,3,5,13-pentamethoxy-6,7-dimethyl-1,2,3,4,4a,5,6,7,8,13b-decahydrobenzo[3′,4′]cycloocta[1′,2′:4,5]benzo[1,2-d][1,3]dioxole, C24H30O7
  62. Crystal structure of bis(6-carboxyhexyl)-4,4′-bipyridinium dibromide – 2,6-dihydroxynaphthalene (1/2), C42H46Br2N2O8
  63. Crystal structure of methyl 2-(2-chloroacetyl)-1-(4-(methoxycarbonyl)phenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H21ClN2O5
  64. Crystal structure of bis(dimethylammonium) poly[{μ4-1,1ʹ-(1,4-phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato)-κ6N4O2}zinc(II)], C22H26N6O8Zn
  65. Crystal structure of 2-(2-(4-methoxyphenyl)-2H-indazol-3-yl)acetonitrile, C16H13N3O
  66. Crystal structure of (E)-7-methoxy-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H23NO3
  67. The crystal structure of N′1,N′2-bis((E)-3-(tert-butyl)-2-hydroxybenzylidene)oxalohydrazide, C24H30N4O4
  68. The crystal structure of trimethyl 2,2′,2′′-(benzene-1,3,5-triyltris(oxy))triacetate, C15H18O9
  69. Crystal structure of bis(N,N-dimethylformamide-κO)-bis(pyridine-2-carboxylato-κ2N,O)-bis(μ2-pyridine-2-carboxylato-κ2N,O)-dinickel(II), C30H30N6Ni2O10
  70. Crystal structure of bis(μ2-1-pyrenecarboxylato-κ3O,O′:O′)-bis(1-pyrenecarboxylato-κ2O,O′)-(benzimidazole-κ1N)dicadmium(II), C82H48Cd2N4O8
  71. One-pot synthesis and crystal structure of diethyl 2,6-dimethyl-4-(1-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylate, C21H23N5O6
  72. The crystal structure of 1-(2-fluorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-carbonitrile, C18H13FN2O2
  73. Crystal structure of bis(trimethylphenylammonium) aqua-oxido-octathiotritungstate, (Me3PhN)2[W3OS8(H2O)]
  74. The crystal structure of trichlorido[N-[(2-oxyphenyl)methylidene]phenylglycinemethylester-κ3O,N,O′]-tin(IV) – methylene chloride (1/1), C16H14Cl3NO3Sn·CH2Cl2
  75. The crystal structure of furan-2,5-diylbis((4-chlorophenyl)methanol), C18H14Cl2O3
  76. The crystal structure of hexalithium decavanadate hexadecahydrate, H32Li6O44V10
  77. Crystal structure of ethyl 4-{[5-(adamantan-1-yl)-2-sulfanylidene-2,3-dihydro-1,3,4-oxadiazol-3-yl]methyl}piperazine-1-carboxylate, C20H30N4O3S
  78. Crystal structure of aqua(μ2-2,2′,2″-((nitrilo)tris(ethane-2,1-diyl(nitrilo)methylylidene))tris (6-ethoxyphenolato))(pentane-2,4-dionato-κ2O,O′)-dinickel(II), C38H48N4Ni2O9
https://doi.org/10.1515/ncrs-2022-0511
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of methyl 2-((4-chloro-2-fluoro-6-((2,2,2-trifluoroethyl) thio)phenoxy)methyl)benzoate, C17H13ClF4O3S
  4. The crystal structure of 3-hydroxy-5-oxo-4-propanoylcyclohex-3-ene-1-carboxylic monohydrate, C10H14O6
  5. Crystal structure of 2-({[5-(adamantan-2-yl)-2-sulfanylidene-1,3,4-oxadiazolidin-3-yl]methyl}amino)benzonitrile, C20H22N4OS
  6. Crystal structure of 1-(3-bromopropyl)-2-((4-chlorophenoxy)methyl)-4-methyl-1H-benzo[d]imidazole, C18H18BrClN2O
  7. Crystal structure of 2-methoxy-6-[(2-morpholin-4-yl-phenylamino)-methylene]-4-nitro-cyclohexa-2,4-dienone, C18H19N3O5
  8. The crystal structure of 2-(7-(2,3-dimethoxyphenyl)-[1,2,4]triazolo[1,5-a]-pyrimidin-5-yl)-3-methoxyphenol, C20H18N4O4
  9. The crystal structure of 3-(1-(2-(4-hydroxy-3,5-dimethoxybenzylidene)hydrazinyl)ethylidene)chroman-2,4-dione dihydrate, C20H22N2O8
  10. Crystal structure of 3,5,7-trimethoxy-3′,4′-methylenedioxy-flavone, C19H16O7
  11. The crystal structure of strictic acid, C20H26O3
  12. Crystal structure of 1,1′-(pyrazine-1,4-diyl)-bis(propan-2-one), C10H14N2O2
  13. The crystal structure of 1-(adamantan-1-yl)-3-(4-chlorophenyl)urea, C17H21ClN2O
  14. The crystal structure of (2R,6′R)-2′,7-dichloro-4,6-dimethoxy-6′-methyl-3H-spiro[benzofuran-2,1′-cyclohexan]-2′-ene-3,4′-dione, C16H14Cl2O5
  15. Synthesis and crystal structure of 1-((3R,10S,13R,17S)-3-((4-methoxyphenyl)amino)-10,13-dimethylhexadecahydro-1H-cyclopenta[α]-phenanthren-17-yl)ethan-1-one, C28H41NO2
  16. Crystal structure of N-2,6-difluorobenzoyl-N′-[1-(3-chloro-4-methyl-phenyl)-4-cyano-1H-pyrazol-5-carbamoyl]urea, C19H12ClF2N5O2
  17. Crystal structure of (−)-β-D-19-glucopiranosyl-9,15-dihydroxy kaurenoate, C26H40O9
  18. Crystal structure of 7-hydroxy-6-(2-hydroxyethyl)-2H-chromen-2-one, C11H10O4
  19. Crystal structure of S-(benzo[d]thiazol-2-yl)-N-(tert-butyl)thiohydroxylamine, C11H14N2S2
  20. Crystal structure of poly[di-µ2-aqua-aqua-nitrato-κ2O,O′-(µ3-2-nitroisophthalato-κ4O,O′:O″:O′″)barium(II)natrium(II)] monohydrate, C8H11BaN2NaO13
  21. The crystal structure of diaqua-bis(pyrazolo[1,5-a]pyrimidine-3-carboxylato-κ2 N,O)-cobalt(II) dihydrate, C14H16N6O8Co
  22. Crystal structure of (S,E)-3-((pyridin-2-ylmethylene)amino)-2-(pyridin-4-yl)-2,3- dihydroquinazolin-4(1H)-one monohydrate, C19H15N5O⋅H2O
  23. Synthesis and crystal structure of 5-(8-(((5-carboxypentyl)ammonio)methyl)-7-hydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxy-3-nitrobenzenesulfonate monohydrate, C22H24N2O12S
  24. Synthesis and crystal structure of 8-bromo-3-(1H-pyrazole-1-carbonyl)-2H-chromen-2-one, C13H7BrN2O3
  25. Crystal structure of E-7-fluoro-2-(4-methoxy-3-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  26. Hydrogen bonded dimers in the crystal structure of 2-chloro-N-((3,5-dimethylphenyl)carbamoyl)-nicotinamide, C30H28Cl2N6O4
  27. Crystal structure of 3,3′-(1,4-phenylenebis(methylene))bis(1-allyl-1H-imidazol-3-ium) bis(hexafluoro phosphate)(V), C10H12F6N2P
  28. Crystal structure of (E)-7-bromo-2-(4-(4-methylpiperazin-1-yl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H23BrN2O
  29. Crystal structure of pentacarbonyl-(μ2-ethane-1,2-dithiolato-κ4S:S,S′:S′)-(diphenyl(o-tolyl)phosphine-κ1P)diiron (Fe–Fe), C26H21Fe2O5PS2
  30. Crystal structure of 9-(2-chloroethoxy)-4-(4-methoxy-3-(trifluoromethyl)phenyl)- 5,6-dihydrobenzo[h]quinazolin-2-amine, C22H19ClF3N3O2
  31. Crystal structure of triaqua-[5-bromo-2-(carboxylatomethoxy)benzoate-κ3 O,O′,O″]nickel(II), C9H11BrNiO8
  32. The crystal structure of 4,4′-dichloro-3,5′-diphenyl-1′H-1,3′- bipyrazole, C18H12Cl2N4
  33. The crystal structure of bis(1H-pyrazole-carboxamidine-κN,N′)bis(nitrato-κO)-copper(II), C8H12CuN10O6
  34. Synthesis and crystal structure of 3-bromo-4-phenyl-2H-chromene, C15H11BrO
  35. Crystal structure of (E)-5-(diethylamino)-2-((morpholinoimino)methyl)phenol, C15H23N3O2
  36. Crystal structure of niobium trigallide, NbGa3
  37. Crystal structure of dimethyl 4,4′-(((1R, 2R)-cyclohexane-1,2-diyl)bis(azanediyl))dibenzoate, C22H26N2O4
  38. Crystal structure of dimethyl 4,4′-((4R, 5R)-4,5-diphenylimidazolidine-1,3-diyl)dibenzoate, C31H28N2O4
  39. The crystal structure of 2-(2-bromophenyl)-4-phenylbenzo[b][1,4]oxaphosphinine 4-oxide, C20H14BrO2P
  40. The crystal structure of 3-hydroxy-2-nitroestra-1,3,5(10)-trien-17-one, C18H21NO4
  41. Crystal structure of catena-poly[[μ2-1,3-bis[(1H-imidazol-1- yl)methyl]benzene-N:N′]-(μ2–D–camphorato-O, O′: O″, O‴)cadmium(II)], C48H56Cd2N8O8
  42. Crystal structure of N-(4-bromophenyl)-4-[3-(trifluoromethyl)phenyl]-piperazine-1-carbothioamide, C18H17BrF3N3S
  43. The crystal structure of cis-Dicyano-bis(2,2′-bipyridine)k2N,N′-chromium(III) hexafluorophosphate, C22H16N6F6PCr
  44. Crystal structure of 4-((6-bromohexyl)oxy)-2-hydroxybenzaldehyde, C13H17BrO3
  45. Crystal structure of hydrazinium methanesulfonate, CH8N2O3S
  46. Crystal structure of 1-(2-iodobenzoyl)-6-methoxy-1H-indole-3-carbaldehyde, C17H12INO3
  47. Crystal structure of bis(acridinium) tetrabromidomanganate(II), C26H20Br4MnN2
  48. The crystal structure of 6,6′-((1E,1′E)-hydrazine-1,2-diylidenebis(methanylylidene)) bis(2-(tert-butyl)phenol), C22H28N2O2
  49. The crystal structure of the cocrystal di-μ2-chlorido-tetramethyl-tetraphenyl-di-μ3-oxido-dichloridotetratin(IV) – diphenyl-methyl-chloridotin(IV)(1/2), C54H58Cl6O2Sn6
  50. Crystal structure of (3a7R,13bR)-3-((1R)-1-hydroxy-1-(5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-3a,11,11,13b-tetramethyl-2,3,3a,4,5,11,11a,12,13,13b-decahydroindeno[5′,4′:4,5] cyclohepta[1,2-c]oxepin-9(1H)-one, C30H40O5
  51. Crystal structure of 1-(4-methoxyphenyl)-2-phenoxyethan-1-one, C15H14O3
  52. Crystal structure of trans-tetrakis(3-phenylpyridine-κN)bis(thiocyanato-κN)nickel(II), C46H36N6NiS2
  53. Crystal structure of sodium catena-poly[bis(thiourea-κ1S)-tetrakis(μ2-thiourea-κ2S,S)tricopper(I)] difumarate, C14H29Cu3N12NaO8S6
  54. Crystal structure of bis(benzylamine-κ1N)-bis((E)-2-methyl-3-phenylacrylato-κ1O)copper(II), C34H36CuN2O4
  55. The crystal structure of 3,4-dihydroxybenzoic acid – 3-[7-{[2-(3,4-difluorophenyl)cyclopropyl]amino}-5-(propylsulfanyl)-3H-[1,2,3] triazolo[4,5-d]pyrimidin-3-yl]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol – water (1/1/1), C30H36F2N6O9S
  56. Crystal structure of catena-poly[dipyridine-bis(pyridine-2-carboxylato-κ 2 N,O)-bis(μ 2-pyridine-2-carboxylato-κ 2 N,O)-dinickel(II)], C34H26N6Ni2O8
  57. The crystal structure of 1-((1-methyl-1H-1,2,4-triazol-3-yl) methyl)-3-(2,4,5-trifluorobenzyl)-1,3,5-triazinane-2,4,6-trione, C14H11F3N6O3
  58. Crystal structure of (E)-2-((Z)-2-((1S,4R)-3,3-dimethylbicyclo[2.2.1] heptan-2-ylidene)ethylidene)hydrazine-1-carbothioamide, C24H38N6S2
  59. Crystal structure of photochromic 3-(5-(2,5-dimethylthiophen-3-yl)-2,2,3,3,4,4-hexafluorocyclopentyl)-2-methylbenzo[b]-thiophene, C20H14F6S2
  60. Crystal structure of bis(2,5,5,7-tetramethyl-1,4-diazepane-1,4-diium) diaqua-bis(1,2-diaminopropane)copper(II) bis(μ6-oxido)tetrakis(μ3-oxido)-tetradecakis(μ2-oxido)-octaoxido-decavanadium(V) – water (1/4), C24H76CuN8V10O34
  61. Crystal structure of 1,2,3,5,13-pentamethoxy-6,7-dimethyl-1,2,3,4,4a,5,6,7,8,13b-decahydrobenzo[3′,4′]cycloocta[1′,2′:4,5]benzo[1,2-d][1,3]dioxole, C24H30O7
  62. Crystal structure of bis(6-carboxyhexyl)-4,4′-bipyridinium dibromide – 2,6-dihydroxynaphthalene (1/2), C42H46Br2N2O8
  63. Crystal structure of methyl 2-(2-chloroacetyl)-1-(4-(methoxycarbonyl)phenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H21ClN2O5
  64. Crystal structure of bis(dimethylammonium) poly[{μ4-1,1ʹ-(1,4-phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato)-κ6N4O2}zinc(II)], C22H26N6O8Zn
  65. Crystal structure of 2-(2-(4-methoxyphenyl)-2H-indazol-3-yl)acetonitrile, C16H13N3O
  66. Crystal structure of (E)-7-methoxy-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C22H23NO3
  67. The crystal structure of N′1,N′2-bis((E)-3-(tert-butyl)-2-hydroxybenzylidene)oxalohydrazide, C24H30N4O4
  68. The crystal structure of trimethyl 2,2′,2′′-(benzene-1,3,5-triyltris(oxy))triacetate, C15H18O9
  69. Crystal structure of bis(N,N-dimethylformamide-κO)-bis(pyridine-2-carboxylato-κ2N,O)-bis(μ2-pyridine-2-carboxylato-κ2N,O)-dinickel(II), C30H30N6Ni2O10
  70. Crystal structure of bis(μ2-1-pyrenecarboxylato-κ3O,O′:O′)-bis(1-pyrenecarboxylato-κ2O,O′)-(benzimidazole-κ1N)dicadmium(II), C82H48Cd2N4O8
  71. One-pot synthesis and crystal structure of diethyl 2,6-dimethyl-4-(1-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylate, C21H23N5O6
  72. The crystal structure of 1-(2-fluorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-carbonitrile, C18H13FN2O2
  73. Crystal structure of bis(trimethylphenylammonium) aqua-oxido-octathiotritungstate, (Me3PhN)2[W3OS8(H2O)]
  74. The crystal structure of trichlorido[N-[(2-oxyphenyl)methylidene]phenylglycinemethylester-κ3O,N,O′]-tin(IV) – methylene chloride (1/1), C16H14Cl3NO3Sn·CH2Cl2
  75. The crystal structure of furan-2,5-diylbis((4-chlorophenyl)methanol), C18H14Cl2O3
  76. The crystal structure of hexalithium decavanadate hexadecahydrate, H32Li6O44V10
  77. Crystal structure of ethyl 4-{[5-(adamantan-1-yl)-2-sulfanylidene-2,3-dihydro-1,3,4-oxadiazol-3-yl]methyl}piperazine-1-carboxylate, C20H30N4O3S
  78. Crystal structure of aqua(μ2-2,2′,2″-((nitrilo)tris(ethane-2,1-diyl(nitrilo)methylylidene))tris (6-ethoxyphenolato))(pentane-2,4-dionato-κ2O,O′)-dinickel(II), C38H48N4Ni2O9
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