Home Physical Sciences Crystal structure of 2,7-bis(3,5-diethyl-1H-pyrazol-4-yl)-benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone, C28H26N6O4
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Crystal structure of 2,7-bis(3,5-diethyl-1H-pyrazol-4-yl)-benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone, C28H26N6O4

  • Kiyoshi Fujisawa ORCID logo EMAIL logo , Shuto Sugihara ORCID logo , Kako Iwai ORCID logo , Keigo Amimoto ORCID logo and Edward R. T. Tiekink ORCID logo EMAIL logo
Published/Copyright: September 16, 2025
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 240 Issue 6

Abstract

C28H26N6O4, trigonal, R 3 ‾ (no. 148), a = 20.3056(12) Å, c = 16.3655(10) Å, V = 5843.7(8) Å3, Z = 9, R gt (F) = 0.0511, wR ref (F2) = 0.1523, T = 178 K.

CCDC no.: 2481586

The molecular structure is shown in the figure. Table 1 contains the crystallographic data; the list of the atoms including atomic coordinates and displacement parameters can be found in the cif-file attached to this article.

Table 1:

Data collection and handling.

Crystal: Orange block
Size 0.20 × 0.15 × 0.09 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.09 mm−1
Diffractometer, scan mode: Rigaku XtaLAB P200, ω scan
θmax, completeness: 26.4°, 100 %
N(hkl)measured, N(hkl)unique, Rint: 11,534, 2,649, 0.041
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 1,792
N(param)refined: 185
Programs: Rigaku, 1 IL MILIONE, 2 SHELX, 3 WinGX 4

1 Source of material

The synthesis of 3,5-diethyl-1-pyrazol-4-amine was accomplished in a three-step process. LHpzH: The 3,5-diethyl-1H-pyrazole, was obtained by a modified literature method, 5 by the reaction of 3,5-heptanedione (10.0 g, 78.1 mmol) with hydrazine monohydrate (12.4 mL, 248 mmol, 3.2 equiv.) in ethanol (35 mL) at 373 K for 4 h. After 4 h, the solution was evaporated under vacuum to yield a pale-yellow powder (10.02 g, 80.7 mmol, 103 % yield; the high yield arises due to the presence of some water which was not detectable in the 1H NMR). 1H NMR (CDCl3, 500 MHz): δ 1.24 (t, 6H, 7.5 Hz, CH2CH3), 2.65 (q, 4H, 7.5 Hz, CH2CH3), 5.88 (s, 1H, pz-4H); NpzH not observed. LNO 2 pzH: 3,5–Diethyl-1H-pyrazol-4-nitro was obtained by a modified literature method. 5 The nitration reaction of LHpzH (5.06 g, 40.7 mmol) was achieved using a mixture of concentrated nitric acid (16 mL) and concentrated sulfuric acid (25 mL). After heating at 373 K for 4 h, the cooled reaction mixture was neutralised with sodium hydroxide solution. After the filtration of the precipitated pale-yellow powder, the obtained powder was carefully washed with distilled water. Crystallization from dichloromethane/heptane (2:1 v/v) solution at 273 K yielded a white powder (4.77 g 28.2 mmol, 69 % yield). Anal. calcd. for C7H11N3O2·1/6(H2O) C 48.83, H 6.63, N 24.40 %. Found: C 49.18, H 6.75, N 24.07 %. 1H NMR (CDCl3, 500 MHz): δ 1.31 (t, 6H, 7.5 Hz, CH2CH3), 3.03 (q, 4H, 7.5 Hz, CH2CH3); NpzH not observed. LNH 2 pzH: 3,5–Diethyl-1H-pyrazol-4-amine was obtained by a hydrogenation reaction with palladium on carbon (10 %) catalyst under H2 (1 atm). After drying, LNO2pzH (0.83 g, 4.91 mmol) and Pd/C catalyst (1.0 g) were suspended in methanol (30 mL), and the atmosphere was changed from Ar to H2. The reaction was performed for 4 days at room temperature. The obtained reaction mixture was filtered through Celite to remove undissolved solids. The filtrate was crystallized from dichloromethane at 243 K to yield a colourless powder (0.59 g, 4.24 mmol, 86 % yield). Anal. calcd. for C7H13N3: C 60.40, H 9.41, N 30.19 %. Found: C 60.05, H 9.68, N 30.13 %. 1H NMR (CDCl3, 500 MHz): 1.25 (t, 6H, 7.5 Hz, CH2CH3), 2.59 (q, 4H, 7.5 Hz, CH2CH3); NpzH and NH2 not observed. IR (KBr, cm−1): 3,358 s ν(NH2), 3,291 s ν(N–H), 3,209 s ν(N–H), 2,972 s ν(C–H), 2,935 s ν(C–H), 2,874 s ν(C–H), 1,602 s ν(C=N). Under an Ar atmosphere, the reaction of 3,5-diethyl-1H-pyrazol-4-amine (0.278 g, 2.00 mmol) with naphthalene-1,4,5,8-tetracarboxylic dianhydride (0.236 g, 0.88 mmol) in anhydrous N,N-dimethylformamide (10 mL) was conducted by solvothermal synthesis for 6 days at 393 K. The solvent was then removed in vacuo to yield a brown powder. The brown powder was recrystallized from an anhydrous methanol solution at 273 K to yield a brown powder (0.354 g, 0.693 mmol, 69 % yield). Single crystals for X-ray crystallography were obtained by the slow evaporation at room temperature from an anhydrous acetone solution. Anal. calcd. for C28H26N6O4.0.25(H2O): C 65.29, H 5.19, N 16.32 %. Found: C 65.47, H 5.25, N 16.19 %. 1 H NMR (CDCl3, 500 MHz): 1.21 (t, 12H, 7.5 Hz, CH2CH3), 2.53 (q, 8H, 7.5 Hz, CH2CH3), 8.87 (s, 4H, Ph–H); NpzH not observed. IR (KBr, cm−1): 3,613 m, 3,362 s ν(N–H), 3,078 s ν(C–H), 2,974 s ν(C–H), 2,936 s ν(C–H), 2,877 s ν(C–H), 1,712 s ν(C=O), 1,678 s ν(C=O), 1,582 s ν(C=N).

2 Experimental details

The N- and C-bound H atoms were geometrically placed (N–H = 0.88 Å and C–H = 0.95–0.99 Å) and refined as riding with Uiso (H) = 1.2–1.5Ueq (N, C). The C7-methyl group was disordered over two sites. Each component was refined independently with anisotropic displacement parameters. The major component had a site occupancy factor = 0.768(8). The unit-cell has solvent accessible voids of 104 Å3; see CIF for further details.

3 Discussion

Recently, we described the synthesis and crystallographic characterization of two 4-amino-pyrazoles, 5 , 6 of particular interest since the amino group can be subsequently reacted with different carbonyl functional groups such as aldehyde, 7 carboxylic acid 8 and, as demonstrated herein, carboxylic anhydride. This chemistry opens a new field for the exploration of new, high-dimensional materials. 9 In the present study, the synthesis of a new 4-amino-pyrazole is described, viz. 3,5-diethyl-1H-pyrazol-4-amine, and the product of its reaction with naphthalene-1,4,5,8-tetracarboxylic dianhydride to give the title compound, (I) {systematic name: 6,13-bis(3,5-diethyl-1H-pyrazol-4-yl)-6,13- diazatetracyclo[6.6.2.0{4,16}.0{1,15}]hexadeca-1,3,8,10,15-pentaene-5,7,12,14-tetrone}. Some related chemistry has been published with naphthalene-1,4,5,8-tetracarboxylic dianhydride. 10 , 11

After the nitration reaction of LHpzH with a mixture of concentrated nitric acid and concentrated sulfuric acid, a new compound LNO 2 pzH was obtained in 69 % yield. 6 The hydrogenation reaction of LNO 2 pzH with palladium on carbon (10 %) catalyst under an H2 (1 atm) atmosphere yielded a colourless powder of LNH 2 pzH in 86 % yield. This material, LNH 2 pzH, can be also obtained by a modified method using NaNO2/HCl/NH2NH2. 6 However, the latter reaction yielded the product in low yield, i.e. 28 %. The IR spectrum of LNH 2 pzH features a characteristic absorption band at 3,358 cm−1, assigned to amine–NH2 stretching and a strong absorption band at 3,291 cm−1 which is assigned to pyrazolyl–N–H stretching. The expected signals in the 1H NMR spectrum of LNH 2 pzH at 1.25 ppm (methyl–H) and 2.59 ppm (methylene–H), are shifted upfield compared to those of the precursor, LNO 2 pzH, at 1.31 ppm and 3.03 ppm. New, characteristic absorption bands were observed in the IR spectrum of (I). Thus, the sharp N–H2 stretching band in the spectrum of the LNH 2 pzH precursor disappeared and the band at 3,291 cm−1 was shifted to 3,362 cm−1 in the spectrum of (I). The C=N stretching bands of LNH 2 pzH at 1,602 cm−1 was clearly shifted to 1,582 cm−1 in (I), and two new C=O bands at 1,712 and 1,678 cm−1 were observed and shifted from 1,781 to 1,766 cm−1 observed for naphthalene-1,4,5,8-tetracarboxylic dianhydride.

The molecular structure of (I) is illustrated in the upper view of the figure (35 % displacement ellipsoids; the minor part of the disorder is omitted for clarity). The molecule is disposed about a centre of inversion and comprises a central tetrone molecule [r.m.s. = 0.044 Å; maximum deviation = +/−0.090(2) for the C8 atoms] connected at each nitrogen atom to a 3,5-diethyl-1H-pyrazol-4-yl ring. The dihedral angle between the N1- and N3-rings is 80.94(11)°, indicating a near to perpendicular relationship. The confirmation of protonation at the N1 atom in the pyrazolyl ring rather than at the N2 atom is seen in the disparity in the C3–N1–N2 [113.84(16)°] and C5–N2–N1 [104.19(17)°] angles and in the pattern of hydrogen-bonding (see below). Within the pyrazolyl ring, the C3–N1 [1.350(2) Å] bond length is significantly longer than the C5–N2 [1.333(3) Å] bond. In the same way, C4–C5 [1.399(3) Å] is longer than the C3–C4 [1.364(3) Å] bond; the N1–N2 bond length is 1.352(2) Å. These results suggest limited delocalisation of π-electron density over the five-membered ring. The ethyl groups on each pyrazolyl residue lies to opposite sides of the ring.

Conventional hydrogen-bonding features in the molecular packing, namely pyrazolyl–N–H⋯O(carbonyl) [N1–H1n⋯O2i: H1n⋯O2i = 2.19 Å, N1⋯O2i = 2.885(2) Å with the angle subtended at H1n = 136° for symmetry operation (i) 7/3 – x, 2/3 – y, 2/3 – z] interactions which occur within linear chains approximately parallel to [2 0 1], as illustrated in the lower view of the figure (non-acidic hydrogen atoms have been omitted for clarity).

Corresponding authors: Kiyoshi Fujisawa, Department of Chemistry, Ibaraki University, Mito, Ibaraki 310–8512, Japan, ; and Edward R. T. Tiekink, Department of Chemistry, Universitat de les Illes Balears, Crta de Valldemossa km 7.5, 07122, Palma de Mallorca, Spain, E-mail:

Acknowledgments

This research was supported by the Joint Usage/Research Centre for Catalysis and the Koyanagi Foundation.

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

  2. Conflict of interest: The authors declare no conflicts of interest.

  3. Research funding: This study was financially supported by the Joint Usage/Research Centre for Catalysis (Proposals 23DS0198, 24ES0584 and 25DS0752).

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Received: 2025-06-27
Accepted: 2025-08-21
Published Online: 2025-09-16
Published in Print: 2025-12-17

© 2025 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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  4. Refinement of crystal structure of 2-(2,3-dihydro-3-oxo-1 H -inden-1-ylidene)-1 H -indene-1,3(2 H )-dione C18H10O3
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https://doi.org/10.1515/ncrs-2025-0290
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of (1Z, 2Z)-3-phenyl-2-propenal 2-(4-bromo-2-fluorophenyl)hydrazone, C15H12BrFN2
  4. Refinement of crystal structure of 2-(2,3-dihydro-3-oxo-1 H -inden-1-ylidene)-1 H -indene-1,3(2 H )-dione C18H10O3
  5. The crystal structure of 3-(1-fluoro-2-(naphthalen-2-yl)-2-oxoethyl)-2-methoxy-3,4-dihydroisoquinolin-1(2H)-one, C22H18FNO3
  6. Crystal structure of the dinuclear copper(II) complex bis(μ2-2,2′ -{[1,3-phenylenebis-(methylene)]bis(oxy)}dibenzoaot-κ4O,O′:O′′,O′′′)-bis(dimethylformamide-κ1O)dicopper(II), C50H44Cu2N2O14
  7. Crystal structure of poly[triaqua-(μ9-biphenyl-3,3′,5,5′-tetracarboxylic-κ8 O,O:O,O′: O,O″:O,O‴)samarium(III)sodium(I)], C16H12NaSmO11
  8. The crystal structure of 5-benzyl-1-(4-fluorobenzyl)-4-((4-fluorobenzyl)oxy)-1,5-dihydro-2H-pyrrol-2-one, C25H21F2NO2
  9. The crystal structure of diammonium 2,5-dihydroxyterephthalate, C8H12N2O6
  10. Crystal structure of (E)-4-(4-(1H-1,2,4-triazol-1-yl)benzylidene)-6,8-dimethoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, C21H19N3O4
  11. Crystal structure of poly[oktakis(μ2-oxido-κ2O:O)-tetrakis(oxido-κ1O)-bis(μ2-1,1′-[1,4-phenylenebis(methylene)]di(1H-imidazole-κ2N:N′))-tetravanadium(V)-dizinc(II)] monohydrate, C28H30Zn2N8O13V4
  12. Crystal structure of acotiamide hydrochloride dimethylacetamide solvate (1/1), C25H40ClN5O6S
  13. Crystal structure of catena-poly[monoaqua (u2-(3-(3,5-dicarboxyphenyl)pyridine-2,6-dicarboxylic-k4O:O′:O″:N)zinc(II))] monohydrate, C15H11NO10Zn
  14. Crystal structure of dichlorido{2,6-bis(3,5-diisopropyl-N-pyrazolyl)pyridine}zinc(II), C23H33Cl2N5Zn
  15. Crystal structure of nitrato-κ2O,O′-[hydridotris(3,5-diethylpyrazol-1-yl)borato-κ3N,N′,N″]copper(II), C21H34BCuN7O3
  16. Crystal structure of 2,7-bis(3,5-diethyl-1H-pyrazol-4-yl)-benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetrone, C28H26N6O4
  17. Crystal structure of 2-(4-chlorophenyl)benzothiazole, C13H8ClNS
  18. Synthesis and crystal structure (3R,4′S)-4′-(3,5-dibromophenyl)-1′-methyl-2H-dispiro [benzofuran-3,3′-pyrrolidine-2′,2″-indene]-1″,2,3″-trione, C26H17Br2NO4
  19. Crystal structure of bis(((3a,7a-dihydro-1H-benzo[d][1,2,3]triazol-1-yl)methyl) triphenylphosphonium) tetrachloridomanganate(II), C50H42Cl4MnN6P2
  20. The crystal structure of 4,9-bis(4-chlorophenyl)-1,6-bis(2-cyanobenzyl)-2,4a,5,6,7,7a-hexahydro-1H-2,7,5-(epiprop[2]ene[1,1,3]triyl)pyrrolo[3,4-b]pyridine-3,10-dicarbonitrile, C40H26Cl2N6
  21. The crystal structure of poly((μ2-3-(3-nitro-4-carboxylphenyl)benzoate-κ3O, O′:O″)-μ2-1,4-bis(1-imidazolyl)benzene-κ2N:N′-cadmium(II)), C26H17N5O6Cd
  22. The crystal structure of 6-hydroxy-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione monohydrate, C7H6N2O4
  23. Crystal structure of 4-((cyclohexylsulfonyl)methyl)-1,2,3,4-tetrahydrobenzo [4,5]imidazo[1,2-a]pyridine, C18H24N2O2S
  24. Crystal structure of 4,7-diphenyl-1,10-phenanthroline-κ2N,N′)-bis(2,4-di(fluorine)-1-phenylpyridine-κ2C,N)-iridium(III) hexafluorophosphate–dichloromethane (1/1), C47H30Cl2F10IrN4P
  25. Crystal structure of (4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)boronic acid, C19H15BN2O2
  26. The crystal structure of (E)-(2-((pyridin-2-ylmethylene)amino)phenyl)arsonic acid, C12H11AsN2O3
  27. The crystal structure of N(benzyl(phenyl)carbomothioyl)benzamide, C21H18N2OS
  28. The crystal structure of bis(2-picolinium) hexachlorostannate dichloromethane monosolvate, C13H18Cl8N2Sn
  29. Crystal structure of poly[tetraaqua-bis(μ4-3–1-(carboxylatomethyl)-1H-1,2,4-triazole-3-carboxylato)-κ4O:O′,O″,N)zinc(II)], C5H7N3O6Zn
  30. The crystal structure of the co-crystal isonicotinamide – 2-(nitrophenyl)methanol (1/1), C6H6N2O·C7H7NO3
  31. The crystal structure of 4-(3-carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 2-fluorobenzoate hydrate, C23H25F2N3O6
  32. Crystal structure of [diaqua-{1H-benzo[d]imidazol-3-ium-5,6-dicarboxylato-κ2O,O′}magnesium(II)] C18H14MgN4O10
  33. Crystal structure of (3-(dimethoxymethyl)-5-methoxy-1H-indol-1-yl) (2-iodo-5-methoxyphenyl)methanone, C20H20INO5
  34. The crystal structure of 3,7,11-trimethylbenzo[5,6][1,4]thiazino[2,3,4-kl]phenothiazine 5,5,9,9-tetraoxide, C21H17NO4S2
  35. Crystal structure of tris(piperazine-1,4-diium)bis(2-hydroxy-1,2,3-propane-tricarboxylate) pentahydrate, C24H56N6O19
  36. Crystal structure of 2-chloro-5-((5-isopropyl-2-methylphenoxy)methyl)pyridine, C16H18ClNO
  37. Crystal structure of (E)-4-(4-(1H-pyrrol-1-yl)benzylidene)-6,8-dimethoxy-3,4-dihydrobenzo[(b)]oxepin-5(2H)-one, C23H21NO4
  38. Crystal structure of (E)-N′-(3,4-dichlorobenzylidene)-3,4,5-trimethoxybenzohydrazide, C17H16Cl2N2O4
  39. The crystal structure of 2-(2-hydroxyphenyl)-3-(pyridin-2-yl)-2,3- dihydroquinazolin-4(1H)-one, C19H15N3O2
  40. Crystal structure of 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-8-methylchroman-4-one, C17H16O5
  41. Crystal structure of bis[(3,4-dimethoxybenzyl)triphenylphosphonium]di-μ2-bromido-dibromidodicopper(I)
  42. Crystal structure of bis [(1,3-dioxolan-2-ylmethyl)triphenylphosphonium] tetrabromidodicopper(I), C22H22Br2CuO2P
  43. Crystal structure of [1-(4-carboxyphenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylic acid], C12H8N2O5
  44. The crystal structure of one-dimensional cooridnation polymer bis(thiocyanato)-bis((1E,2E)-1,2-bis(1-(pyridin-3-yl)ethylidene)-hydrazine κ2N:N)iron(II), (C30H28N10S2Fe)n
  45. Crystal structure of ((4-acetamidophenyl)sulfonyl)-l-alanine, C11H14N2O5S
  46. Crystal structure of [(1-naphthalen-1-yl-methyl)triphenylphosphonium] dichloridocopper(I), [C29H24P]+[CuCl2]−
  47. RbTm3S5: the first rubidium lanthanoid(III) sulfide with CsEr3Se5-type crystal structure
  48. Crystal structure of 2,2′-((ethane-1,2-diylbis(methylammoniumdiyl))bis(methylene))bis(pyridin-1-ium) diiodido-tris(μ2-iodido-κ2I:I)dicopper(II) chloride dihydrate, C16H30Cu2I6N4O2
  49. The crystal structure of 4-(trifluoromethyl)pyridine-2-carboxylic acid, C7H4F3NO2
  50. The crystal structure of (E)-2-ethoxy-1-methoxy-4-(2-(methylsulfonyl)vinyl)benzene, C12H16O4S
  51. Crystal structure of potassium 1H,1H,2H,2H-perfluorooctanesulfonate, C8H4O3F13SK
  52. Crystal structure of 4-(4-(quinolin-8-yloxy)-1,2,5-thiadiazol-3-yl)morpholine, C15H14O2N4S
  53. The crystal structure of 1,4-bis(bromomethyl)-2,5-dimethylbenzene, C10H12Br2
  54. The crystal structure of imidazo[4,5-e][1,3]diazepine-4,6,8-triamine methanol solvate, C7H11N7O
  55. The crystal structure of chlorido-bis(1,10-phenantroline-κ2N,N′)-(2-formylphenoxyacetato-κ2O,O) lead(II), C33H23N4O4ClPb
  56. Crystal structure of pyridinium tetrakis(1,1,1-trifluoro-2,4-pentadionato-κ2O,O′)yttrium(III) C20F12H16YO8C5H6N
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