Home Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-bis(propan-2-yl)-1H-pyrazol-4-amine, C26H36N6
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Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-bis(propan-2-yl)-1H-pyrazol-4-amine, C26H36N6

  • Kiyoshi Fujisawa ORCID logo EMAIL logo , Keigo Ageishi and Edward R. T. Tiekink ORCID logo EMAIL logo
Published/Copyright: August 15, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 5

Abstract

C26H36N6, triclinic, P 1 ‾ (no. 2), a = 5.7137(2) Å, b = 10.4374(3) Å, c = 11.1141(3) Å, α = 104.980(3)°, β = 94.279(3)°, γ = 93.876(3)°, V = 635.89(3) Å3, Z = 1, R gt (F) = 0.0503, wR ref (F2) = 0.1220, T = 178 K.

CCDC no.: 2285559

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: Yellow plate
Size: 0.07 × 0.06 × 0.01 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.07 mm−1
Diffractometer, scan mode: Rigaku XtaLAB P200, ω
θmax, completeness: 29.5°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 21,711, 3240, 0.053
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 2113
N(param)refined: 152
Programs: CrysAlisPRO [1], IL MILIONE [2], SHELX [3], WinGX/ORTEP [4]
Table 2:

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

Atom X y z Uiso*/Ueq
N1 0.1000 (2) 0.12351 (11) 0.46106 (11) 0.0293 (3)
H1N 0.133 (3) 0.1034 (15) 0.5329 (10) 0.035*
N2 −0.0513 (2) 0.03672 (11) 0.37231 (11) 0.0292 (3)
N3 0.0993 (2) 0.30851 (11) 0.23643 (10) 0.0260 (3)
C1 0.5676 (3) 0.28535 (19) 0.54768 (19) 0.0532 (5)
H1A 0.527942 0.225032 0.599105 0.080*
H1B 0.678888 0.359121 0.596878 0.080*
H1C 0.639602 0.236620 0.474085 0.080*
C2 0.2369 (3) 0.42227 (16) 0.61729 (16) 0.0453 (4)
H2A 0.098711 0.460681 0.588170 0.068*
H2B 0.352990 0.494022 0.665484 0.068*
H2C 0.188932 0.365351 0.670439 0.068*
C3 0.3449 (3) 0.34005 (14) 0.50578 (14) 0.0303 (4)
H3 0.391519 0.400907 0.453679 0.036*
C4 0.1730 (2) 0.23160 (13) 0.42531 (13) 0.0243 (3)
C5 0.0581 (2) 0.21652 (13) 0.30708 (12) 0.0232 (3)
C6 −0.0787 (2) 0.09167 (13) 0.27724 (12) 0.0237 (3)
C7 −0.2304 (3) 0.01690 (13) 0.16101 (13) 0.0279 (3)
H7 −0.185876 0.054919 0.091160 0.033*
C8 −0.4896 (3) 0.03591 (18) 0.17697 (15) 0.0435 (4)
H8A −0.536192 0.002564 0.247220 0.065*
H8B −0.585968 −0.013431 0.100224 0.065*
H8C −0.513273 0.130798 0.193737 0.065*
C9 −0.1904 (3) −0.13078 (15) 0.12481 (16) 0.0457 (4)
H9A −0.021933 −0.140534 0.118713 0.069*
H9B −0.278414 −0.174477 0.043833 0.069*
H9C −0.244996 −0.172129 0.188661 0.069*
C10 −0.0620 (3) 0.32335 (13) 0.15701 (13) 0.0263 (3)
H10 −0.210474 0.273495 0.148718 0.032*
C11 −0.0273 (2) 0.41457 (13) 0.07777 (12) 0.0247 (3)
C12 0.1824 (3) 0.49322 (14) 0.08688 (14) 0.0307 (3)
H12 0.308503 0.489268 0.146214 0.037*
C13 −0.2088 (3) 0.42275 (14) −0.01003 (14) 0.0312 (3)
H13 −0.353387 0.369568 −0.017252 0.037*

1 Source of material

Under an argon atmosphere, the reaction of 4-amino-3,5-diisopropyl-1-pyrazole (0.1004 g, 0.600 mmol) with terephthalaldehyde (0.0439 g, 0.327 mmol) in anhydrous methanol (10 mL) was conducted at room temperature for four days. The solvent was then removed in vacuo. Yellow crystals of (I), were obtained by the slow evaporation at room temperature from an anhydrous methanol and n-heptane solution (4:1 v/v) of (I). Yield: 0.0454 g, 0.105 mmol, 35 % yield. The yield was improved (up to 61 %) by dehydration with molecular sieves 3 Å in methanol/n-heptane solution. Anal. Calcd. for C26H36N6: C 72.19, H 8.39, N 19.42 %. Found: C 71.91, H 8.56, N 19.30 %. 1H NMR (CDCl3, 500 MHz): δ 1.35 (d, 24H, 7 Hz, CH(CH3)2), 3.23 (sept, 4H, 7 Hz, CH(CH3)2), 7.93 (s, 4H, (C6H4)), 8.48 (s, 2H, CH=N); NH not obs. 13C{1H} NMR (CD3OD, 125 MHz): δ 22.8 (CH(CH3)2), 26.3 (CH(CH3)2), 27.9 (CH(CH3)2), 128.6 (4C-pyz), 129.7 (2,3,4,5C–benzene), 140.7 (1,6C–benzene), 152.4 (3,5C–pyz), 159.6 (CH=N). IR (KBr, cm−1): 3207s ν(N–H), 3118 s, 3050 s, 2962 s ν(C–H), 2926 s ν(C–H), 2869 s ν(C–H), 1609 m ν(C=N), 1488 s, 1012 s. Far–IR (CsI, cm−1): 633 s, 539 s, 243 m. Raman (neat solid, cm−1): 1599 s, 1559 s, 1224 m, 1161 m. Solution UV–vis (CH3OH, λmax, nm) (ε, M−1 cm−1): 231 (18,450), 291 (16,820), 370 (23,190). Solid UV–vis (Nujol, λmax, nm): 236, 305, 394. Diffuse Reflectance (solid, nm): 238, 300, 396.

2 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 N-bound H atom was located in a difference Fourier map and refined with N–H = 0.88 Å and with Uiso(H) = 1.2Ueq(N). Owing to poor agreement, three reflections, i.e. (0 1 0), (0 0 1) and (0 −1 1), were omitted from the final cycles of refinement.

3 Comment

Recently, the crystal structure of amine group-introduced pyrazole, i.e. 4-amino-3,5-diisopropyl-1-pyrazole (L1HpzNH2) was described [5]. The compound was obtained by the reduction 4-nitro-3,5-diisopropyl-1-pyrazole with iron powder [5]. The synthetic method and structure of this molecule can be compared to the analogous molecule with methyl groups replacing the isopropyl substituents, i.e. 4-amino-3,5-methyl-1-pyrazole [6]. Originally, 4-amino-3,5-methyl-1-pyrazole was obtained by the direct nitration of acetylacetone with sodium nitrite (NaNO2). This amino group can readily react with aldehydes to generate covalent organic frameworks [7], [8], [9]. Thus, L1HpzNH2 can react readily with terephthalaldehyde (benzene-1,4-dicarboxaldehyde) to yield the title compound I; systematic name: (NE)–N-[(4-{N-[3,5-bis(propan-2-yl)-1H-pyrazol-4-yl]carboximidoyl}phenyl)-methylidene]-3,5-bis(propan-2-yl)-1H-pyrazol-4-amine.

New characteristic absorption bands were observed in the IR spectrum of (I). Thus, the sharp N–H2 stretching band in the spectrum of the L1HpzNH2 precursor at 3374 cm−1 disappeared and the band at 3211 cm−1 was shifted to 3207 cm−1 in the spectrum of (I). The C=N stretching bands of L1HpzNH2 at 1599 cm−1 was clearly separated into two bands at 1609 and 1575 cm−1, and the C=O band at 1693 cm−1, due to terephthalaldehyde, disappeared. In addition, new absorption bands at 231 nm (ε, 18,450 M−1 cm−1), 291 nm (ε, 16,820 M−1 cm−1) and 370 (ε, 23,190 M−1 cm−1) in the UV–vis spectrum of (I), which were clearly different from the spectrum of L1HpzNH2, i.e. an absorption appeared at 238 nm (ε, 4130 M−1 cm−1). The new bands in the spectrum of (I) were also observed in both the solid-state UV–vis and diffuse reflectance spectra, indicating the solid-state structure is retained in solution. The 1H and 13C{1H} NMR exhibited the anticipated signals and in the case of 1H NMR, integration; no resonances were observed for imine N–H.

The molecular structure of (I) was established by X-ray crystallography and is represented in the upper image of the figure (50 % displacement ellipsoids). The molecule is disposed about a centre of inversion and unlabelled atoms are related by the symmetry operation (i): −x, 1 − y, −z. As anticipated, the 1H-pyrazole ring is strictly planar (r.m.s. = 0.010 Å) with the maximum deviation of 0.009(1) Å noted for the C4 atom. Within the ring, the formal C6=N2 [1.3307(17) Å] and C4=C5 [1.3903(19) Å] double bonds are longer than their standard values, and at the same time the formal N1–N2 [1.3585(16) Å], C4–N1 [1.3406(17) Å] and C5–C6 [1.4210(18) Å] single bonds are shorter than their standard values. These results confirm the extensive delocalisation of π-electron density over the five-membered ring. The imine C10=N3 bond length is 1.2736(17) Å, and the C5–N3 link between these residues is 1.4074(16) Å. The overall molecule of (I) is non-planar, there being a twist about the C5–N3 bond [the C4–C5–N3–C10 torsion angle = −152.37(14)°] as seen in the dihedral angle of 29.76(7)° between the five- and six-membered rings. With respect to the pyrazole-bound isopropyl groups, the methine–H atoms are orientated to be directed towards the centre of the molecule.

There are no structural precedents in the literature for molecules related to (I) where a pyrazole ring is directly connected to an imine functionality. However, in an accompanying publication [10], this connectively is described in the di-methanol solvate of the all-methyl analogue of (I). The pyrazole exhibits the same attributes/electronic structure as described for (I). There are examples of molecules whereby the pyrazole ring is connected to a nitrogen atom as in (I) but that nitrogen atom is connected to two carbon atoms, for example when the nitrogen atoms are incorporated at opposite ends of a naphthalene diimide molecule [11]. In the context of the motivation of the synthesis of (I) and related derivatives, it should be mentioned that coordination polymers are formed [12] by molecules of the aforementioned type in their neutral form [11].

Employing Platon [13], an analysis of the molecular packing suggests the presence of both N–H⋯N and C–H⋯π directional interactions between molecules. Thus, pyrazole–N–H⋯N(pyrazole) hydrogen bonds [N1–H1n⋯N2ii: H1n⋯N2ii = 2.060(15) Å, N1⋯N2ii = 2.8141(17) Å with angle at H1n = 142.2(14)° for (ii): −x, −y, 1 − z] link molecules into supramolecular chains. The chain, illustrated in the lower view of the figure (the N–H⋯N hydrogen bonds are shown as orange dashed lines), is orientated along [0 1 −1] and features centrosymmetric, six-membered {⋯HNN}2 synthons. The chains are connected laterally by methyl–C–H⋯π(pyrazole) [C1–H1c⋯Cg(pyrazole)iii: H1c⋯Cg(pyrazole)iii = 2.78 Å with angle at H1c = 149° for (iii) 1 + x, y, z] resulting in supramolecular layers parallel to (0 1 1). Layers stack in an off-set fashion so the alkyl residues occupy regions defined by the phenyl rings of adjacent layers, but without directional interactions between them.

The above geometric analysis of the molecular packing was complemented by the calculation of the Hirshfeld surfaces and of the full and delineated two-dimensional fingerprint plots, using Crystal Explorer 21 [14] and literature protocols [15]. All surface contacts in the crystal of (I) involve H, with the majority being of the type H⋯H, i.e. 69.7 %. The remaining contacts comprise C⋯H/H⋯C [16.7 %] and N⋯H/H⋯N [13.6 %] contacts.

Corresponding authors: Kiyoshi Fujisawa, Department of Chemistry, Ibaraki University, Mito, Ibaraki 310-8512, Japan, E-mail: ; and Edward R. T. Tiekink, Research Centre for Crystalline Materials, School of Medical and Life Sciences, Sunway University, 47500 Bandar Sunway, Subang Jaya, Selangor Darul Ehsan, Malaysia, E-mail:

Acknowledgment

KF is grateful for support from the joint usage/research programme “Artificial Photosynthesis” based at Osaka City University.

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

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

  3. Research funding: This study was supported financially by the Joint Usage/Research Center for Catalysis (Proposals 22DS0143 and 23DS0198).

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Received: 2023-06-29
Accepted: 2023-07-31
Published Online: 2023-08-15
Published in Print: 2023-10-26

© 2023 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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  38. Crystal structure of bis(μ2-2-(1,5-dimethyl–3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino)methyl)phenolato-κ4O:O,N,O′)-(nitrato-κ2O,O′)dicobalt(II), C36H32Co2N8O4
  39. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α] phenanthren-3-one O-(4-fluorobenzoyl) oxime, C28H36FNO2
  40. The crystal structure of 4-aminiumbiphenyl benzenesulfonate, C18H17NO3S
  41. Synthesis and crystal structure of 1-(7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)-N,N-dimethylmethanaminiumnitrate, C18H17N3O9
  42. Crystal structure of N-(Ar)-N′-(Ar′)-formamidine, C14H12Br2N2O
  43. The crystal structure of 4-(2,4-dichlorophenyl)-2-(4-fluorophenyl)-5-methyl-1H-imidazole, C16H11Cl2FN2
  44. Crystal structure of 1-(4–chlorophenyl)-4-benzoyl-3-methyl-1H-pyrazol-5-ol, C17H13ClN2O2
  45. The crystal structure of 5-amino-1-methyl-4-nitroimidazole, C4H6O2N4
  46. Crystal structure of 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene-N,N′-bis(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-1,3,2-diazaborol-2-yl)-l2-germenediamine, C63H94B2GeN8
  47. The crystal structure of (bromido, chlorido)-tricarbonyl-(5,5′-dimethyl-2,2′-bipyridine)-rhenium(I), C15H12Br0.2Cl0.8N2O3Re1
  48. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-bis(propan-2-yl)-1H-pyrazol-4-amine, C26H36N6
  49. The crystal structure of poly[2-(4-carboxypyridin-3-yl)terephthalpoly[diaqua-(μ4-2-(6-carboxylatopyridin-3-yl)terephthalato-κ5O,N:O′:O″,O‴)]) cadmium(II)] dihydrate, C28H20Cd3N2O16
  50. Crystal structure of [tetraaqua-bis((3-carboxy-5-(pyridin-4-yl)benzoate-κ1N)cobalt(II)] tetrahydrate, C26H32CoN2O16
  51. Crystal structure of bis(μ2-azido-κ2N:N)-tetrakis(azido-κ1N)-tetrakis(1,10-phenanthroline-κ2N,N′)dibismuth(III), C48H32N26Bi2
  52. Crystal structure of (Z)-N-(4-(4-(4-((4,5,6-trimethoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)phenoxy)butoxy)phenyl)acetamide, C30H31NO8
  53. Crystal structure of poly[diaqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-bis(μ2-5-carboxybenzene-1,3-dicarboxylato-O,O′:O″)-aqua-di-zinc dihydrate solvate], C27H28N4O16Zn2
  54. Crystal structure of 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile, C12H14N2
  55. Crystal structure of chlorido-(5-nitro-2-phenylpyridine-κ2N,C)-[(methylsulfinyl)methane-κ1S]platinum(II), C13H13ClN2O3PtS
  56. The crystal structure of the co-crystal 1,4-dioxane–4,6-bis(nitroimino)-1,3,5-triazinan-2-one(2/1), C11H19N7O9
  57. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-dimethyl-1H-pyrazol-4-amine di-methanol solvate, C18H20N6·2(CH3OH)
  58. Crystal structure of catena-poly[bis(μ2-azido-k2N:N′)-(nitrato-K2N:N′)-bis(1,10-phenanthroline-K2N:N′)samarium(III)], C24H16N11O3Sm
  59. Crystal structure of (Z)-2-(4-((5-bromopentyl)oxy)benzylidene)-4,5,6-trimethoxybenzofuran-3(2H)-one, C23H25BrO6
  60. Crystal structure of bis(3,5-dimethyl-1H-pyrazol-4-ammonium) tetrafluoroterephthate, 2[C5H10N3][C8F4O4]
  61. Crystal structure of 2-amino-4-(2-fluoro-4-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  62. Crystal structure of 6-(pyridin-3-yl)-1,3,5-triazine-2,4-diamine-sebacic acid (2/1), C13H17N6O2
https://doi.org/10.1515/ncrs-2023-0305
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of (N-([1,1′:4′,1″-terphenyl]-4,4′-diethyl)-2-(bis(pyridin-2-ylmethyl)amino)acetamide-κ4N,N,N″, O)tri(nitrato-kO, O′) samarium(III) - methanol - acetonitrile (1/1/1), C40H39SmN8O14
  4. The crystal structure of 6,6′-(((2-(dimethylamino)ethyl)azanediyl)bis(methylene))bis(2-chloro-4-methyl phenolate-κ4N,N′,O,O′)-(pyridine-2,6-dicarboxylato-N,O,O′)-titanium(IV), C27H27Cl2N3O6Ti
  5. N′-[(1E)-(4–Fluorophenyl)methylidene]adamantane-1-carbohydrazide, C18H21FN2O
  6. Crystal structure of 4-bromo-3-nitro-1H-pyrazole-5-carboxylic acid monohydrate, C4H2N3BrO4·H2O
  7. Crystal structure of dipyridine-k1N-tris(2,2,6,6-tetramethyl-5-oxohept-3-en-3-olato-k2O,O′)dysprosium(III), DyC43H67O6N2
  8. Crystal structure of cyclo[tetraiodido-bis{μ2-1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-isopropyl-imidazol)-k2N:N}dicadmiun(II)], C26H30N10Cd2I4
  9. The crystal structure of tert-butyl (E)-3-(2-(benzylideneamino)phenyl)-1H-indole-1-carboxylate, C26H24N2O2
  10. The crystal structure of 4-(3-carboxy-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4- dihydroquinolin-7-yl)-2-methylpiperazin-1-ium 2,5-dihydroxybenzoate methanol solvate, C27H32FN3O9
  11. Crystal structure of (μ2-1-(4,4′-bipyridine-κ2N:N′)-bis[diaqua-(4-iodopyridine-2,6-dicarboxylato-κ3O,N,O′)–cobalt(II)], C24H20Co2I2N4O12
  12. The crystal structure of dimethyl 4,4′-(10,20-diphenylporphyrin-5,15-diyl)dibenzoate dichloromethane solvate, C49H36N4O4Cl2
  13. (E)-2-((E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-ylidene)hydrazine-1-carbothioamide C14H23N3S1
  14. The crystal structure of [1-(4-(trifluoromethyl)phenyl)-3,4-dihydroquinolin-2(1H)-one], C16H12F3NO
  15. Crystal structure of (E)-2-amino-N′-((3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene)benzohydrazide – dimethylformamide – water (1/1/2), C15H16N4O3·C3H7NO·2H2O
  16. Crystal structure of 3-(4-bromophenyl)-5-methyl-1H-pyrazole, C10H9BrN2
  17. Crystal structure of 1,10-phenanthrolinium bromide dihydrate, C12H9N2Br
  18. Crystal structure of N-(4′-chloro-[1,1′-biphenyl]-2-yl)formamide, C13H10ClNO
  19. The crystal structure of nitroterephthalic acid, C8H5NO6
  20. Crystal structure of (2-((4-bromo-2,6-dichlorophenyl)amino)phenyl) (morpholino)methanone, C17H15BrCl2N2O2
  21. Crystal structure of tetraaqua-bis(ethanol-κO)-tetrakis(μ2-trifluoroacetate-κ2O:O′)-bis(trifluoroacetate-κ2O)digadolinium(III) Gd2C16H20O18F18
  22. The crystal structure of dimethyl 4,4′-[10,20-bis(2,6-difluorophenyl)porphyrin-5,15-diyl]dibenzoate chloroform solvate, C50H32Cl6F4N4O4
  23. The crystal structure of N,N′-((nitroazanediyl)bis(methylene))diacetamide, C6H12O4N4
  24. The crystal structure of [bis(2,2′-bipyridine-6-carboxylato-κ3N,N,O)magnesium(II)]dihydrate, C22H18N4O6Mg
  25. Crystal structure of poly[diaqua-(bis(μ2-1,4-bis(imidazol-1-ylmethyl)benzene)-κ2N,N′] cobalt(II)-tetraqua-bis(1,4-bis(imidazol-1-ylmethyl)benzene)-κ1N)-cobalt(II) di(2,5-thiophenedicarboxylate) dihydrate, C68H76Co2N16O16S2
  26. Crystal structure of poly[chlorido-μ2-chlorido-(μ2-1-[(2-ethyl-4-methyl-1H-imidazol-1-yl)methyl]-1H-benzotriazole-κN:N’)cadmium(II)], C13H15CdN5Cl2
  27. The crystal structure of (4-hydroxybenzenesulfonate)-k1O-6,6′-((1E,1′E)- (ethane-1,2-diylbis(azaneylylidene))bis(methaneylylidene)) bis(2-methoxyphenol)-κ2N,N,μ2O,O,κ2O, O)-(methanol)-cobalt(II) sodium(I), C25H27CoN2NaO9S
  28. Crystal structure of (1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)(4-((2-methyl-6-(trifluoromethyl)pyrimidin-4-yl)amino)piperidin-1-yl)methanone, C17H18F6N6O
  29. Crystal structure of bis{[(cyclohexylimino)(phenylimino)-l5-(methyl)diethylazane-κ2N:N′]-(ethyl)-zinc(II)]}, C38H62N6Zn2
  30. Crystal structure of 2-[(4-bromobenzyl)thio]-5-(5-bromothiophen-2-yl)-1,3,4-oxadiazole, C13H8Br2N2OS2
  31. Crystal structure of 10-methoxy-7,11b,12,13-tetrahydro-6H-pyrazino [2′,3′:5,6]pyrazino[2,1-a]isoquinoline, C15H16N4O
  32. The crystal structure of 1-propyl-2-nitro-imidazole oxide, C6H9N3O3
  33. The crystal structure of 3-nitrobenzene-1,2-dicarboxylic acid–2-ethoxybenzamide (1/1), C17H16N2O8
  34. The structure of RUB-1, (C8H16N)6[B6Si48O108], a boron containing levyne-type zeolite, occluding N-methyl-quinuclidinium in the cage-like pores
  35. The crystal structure of diaqua-(naphthalene-4,5-dicarboxylate-1,8-dicarboxylic anhydride-κ1O)-(4′-(4-(1H-benzimidazolyl-1-yl)phenyl)-2,2′:6′,2″-terpyridine-κ3N,N′,N″)–manganese(II) dihydrate, C42H27MnN5O9·2H2O
  36. Crystal structure of 6,6′-((1E,1′E)-hydrazine-1,2-diylidenebis(methanylylidene))bis (3-(3-bromopropoxy)phenol), C20H22Br2N2O4
  37. The crystal structure of 3-(2-hydroxyphenyl)-4-phenyl-6-(p-tolyl)-2H-pyran-2-one, C24H18O3
  38. Crystal structure of bis(μ2-2-(1,5-dimethyl–3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino)methyl)phenolato-κ4O:O,N,O′)-(nitrato-κ2O,O′)dicobalt(II), C36H32Co2N8O4
  39. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α] phenanthren-3-one O-(4-fluorobenzoyl) oxime, C28H36FNO2
  40. The crystal structure of 4-aminiumbiphenyl benzenesulfonate, C18H17NO3S
  41. Synthesis and crystal structure of 1-(7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)-N,N-dimethylmethanaminiumnitrate, C18H17N3O9
  42. Crystal structure of N-(Ar)-N′-(Ar′)-formamidine, C14H12Br2N2O
  43. The crystal structure of 4-(2,4-dichlorophenyl)-2-(4-fluorophenyl)-5-methyl-1H-imidazole, C16H11Cl2FN2
  44. Crystal structure of 1-(4–chlorophenyl)-4-benzoyl-3-methyl-1H-pyrazol-5-ol, C17H13ClN2O2
  45. The crystal structure of 5-amino-1-methyl-4-nitroimidazole, C4H6O2N4
  46. Crystal structure of 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene-N,N′-bis(1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-1,3,2-diazaborol-2-yl)-l2-germenediamine, C63H94B2GeN8
  47. The crystal structure of (bromido, chlorido)-tricarbonyl-(5,5′-dimethyl-2,2′-bipyridine)-rhenium(I), C15H12Br0.2Cl0.8N2O3Re1
  48. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-bis(propan-2-yl)-1H-pyrazol-4-amine, C26H36N6
  49. The crystal structure of poly[2-(4-carboxypyridin-3-yl)terephthalpoly[diaqua-(μ4-2-(6-carboxylatopyridin-3-yl)terephthalato-κ5O,N:O′:O″,O‴)]) cadmium(II)] dihydrate, C28H20Cd3N2O16
  50. Crystal structure of [tetraaqua-bis((3-carboxy-5-(pyridin-4-yl)benzoate-κ1N)cobalt(II)] tetrahydrate, C26H32CoN2O16
  51. Crystal structure of bis(μ2-azido-κ2N:N)-tetrakis(azido-κ1N)-tetrakis(1,10-phenanthroline-κ2N,N′)dibismuth(III), C48H32N26Bi2
  52. Crystal structure of (Z)-N-(4-(4-(4-((4,5,6-trimethoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)phenoxy)butoxy)phenyl)acetamide, C30H31NO8
  53. Crystal structure of poly[diaqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-bis(μ2-5-carboxybenzene-1,3-dicarboxylato-O,O′:O″)-aqua-di-zinc dihydrate solvate], C27H28N4O16Zn2
  54. Crystal structure of 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile, C12H14N2
  55. Crystal structure of chlorido-(5-nitro-2-phenylpyridine-κ2N,C)-[(methylsulfinyl)methane-κ1S]platinum(II), C13H13ClN2O3PtS
  56. The crystal structure of the co-crystal 1,4-dioxane–4,6-bis(nitroimino)-1,3,5-triazinan-2-one(2/1), C11H19N7O9
  57. Crystal structure of [N(E),N′(E)]-N,N′-(1,4-phenylenedimethylidyne)bis-3,5-dimethyl-1H-pyrazol-4-amine di-methanol solvate, C18H20N6·2(CH3OH)
  58. Crystal structure of catena-poly[bis(μ2-azido-k2N:N′)-(nitrato-K2N:N′)-bis(1,10-phenanthroline-K2N:N′)samarium(III)], C24H16N11O3Sm
  59. Crystal structure of (Z)-2-(4-((5-bromopentyl)oxy)benzylidene)-4,5,6-trimethoxybenzofuran-3(2H)-one, C23H25BrO6
  60. Crystal structure of bis(3,5-dimethyl-1H-pyrazol-4-ammonium) tetrafluoroterephthate, 2[C5H10N3][C8F4O4]
  61. Crystal structure of 2-amino-4-(2-fluoro-4-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  62. Crystal structure of 6-(pyridin-3-yl)-1,3,5-triazine-2,4-diamine-sebacic acid (2/1), C13H17N6O2
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