Acta Crystallographica Section C

Crystal Structure Communications

Volume 65, Part 6 (June 2009)

organic compounds

sk3324 scheme

Acta Cryst. (2009). C65, o303-o310 [ doi:10.1107/S0108270109018964 ]

Seven 5-benzylamino-3-tert-butyl-1-phenyl-1H-pyrazoles: unexpected isomorphisms, and hydrogen-bonded supramolecular structures in zero, one and two dimensions

J. C. Castillo, R. Abonía, J. Cobo and C. Glidewell

Abstract: 5-Benzylamino-3-tert-butyl-1-phenyl-1H-pyrazole, C₂₀H₂₃N₃, (I), and its 5-[4-(trifluoromethyl)benzyl]-, C₂₁H₂₂F₃N₃, (III), and 5-(4-bromobenzyl)-, C₂₀H₂₂BrN₃, (V), analogues, are isomorphous in the space group C2/c, but not strictly isostructural; molecules of (I) form hydrogen-bonded chains, while those of (III) and (V) form hydrogen-bonded sheets, albeit with slightly different architectures. Molecules of 3-tert-butyl-5-(4-methylbenzylamino)-1-phenyl-1H-pyrazole, C₂₁H₂₅N₃, (II), are linked into hydrogen-bonded dimers by a combination of N-H [pi] (arene) and C-H [pi] (arene) hydrogen bonds, while those of 3-tert-butyl-5-(4-chlorobenzylamino)-1-phenyl-1H-pyrazole, C₂₀H₂₂ClN₃, (IV), form hydrogen-bonded chains of rings which are themselves linked into sheets by an aromatic [pi] - [pi] stacking interaction. Simple hydrogen-bonded chains built from a single N-HO hydrogen bond are formed in 3-tert-butyl-5-(4-nitrobenzylamino)-1-phenyl-1H-pyrazole, C₂₀H₂₂N₄O₂, (VI), while in 3-tert-butyl-5-(3,4,5-trimethoxybenzylamino)-1-phenyl-1H-pyrazole, C₂₃H₂₉N₃O₃, (VII), which crystallizes with Z' = 2 in the space group P $\overline{1}$ , pairs of molecules are linked into two independent centrosymmetric dimers, one generated by a three-centre N-H(O)₂ hydrogen bond and the other by a two-centre N-HO hydrogen bond.

Formula: C₂₀H₂₃N₃, C₂₁H₂₂F₃N₃, C₂₀H₂₂BrN₃, C₂₁H₂₅N₃, C₂₀H₂₂ClN₃, C₂₀H₂₂N₄O₂ and C₂₃H₂₉N₃O₃


	Structure factor file (CIF format) (187.0 kbytes) [ doi:10.1107/S0108270109018964/sk3324Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (118.6 kbytes) [ doi:10.1107/S0108270109018964/sk3324IIsup3.hkl ] Contains datablock II

	Structure factor file (CIF format) (206.8 kbytes) [ doi:10.1107/S0108270109018964/sk3324IIIsup4.hkl ] Contains datablock III

	Structure factor file (CIF format) (195.6 kbytes) [ doi:10.1107/S0108270109018964/sk3324IVsup5.hkl ] Contains datablock IV

	Structure factor file (CIF format) (199.6 kbytes) [ doi:10.1107/S0108270109018964/sk3324Vsup6.hkl ] Contains datablock V

	Structure factor file (CIF format) (205.5 kbytes) [ doi:10.1107/S0108270109018964/sk3324VIsup7.hkl ] Contains datablock VI

	Structure factor file (CIF format) (470.5 kbytes) [ doi:10.1107/S0108270109018964/sk3324VIIsup8.hkl ] Contains datablock VII

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