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The fused pyrazole and pyrimidine rings in the title compound, C16H15N3O2, are almost coplanar, being inclined to one another by 1.31 (12)°. The mean plane of this fused ring system is nearly coplanar with the phenyl ring, as indicated by the dihedral angle between their planes of 1.31 (12)°. The fused-ring system and the phenyl ring are nearly coplanar, as indicated by the dihedral angle of 1.27 (10)°. In the crystal, mol­ecules form inversion dimers via pairs of C—H...O hydrogen bonds. C—H...N inter­actions connect the dimers into a three-dimensional network. In addition, π–π contacts are observed, with centroid–centroid distances of 3.426 (2) Å.

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The fused pyrazole and pyrimidine rings in the title compound, C13H10ClN3, are almost coplanar, their planes being inclined to one another by 0.8 (2)°. The mean plane of the fused ring system is nearly coplanar with the phenyl ring, as indicated by the dihedral angle between their planes of 9.06 (7)°.

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The fused pyrazole and pyrimidine rings in the title compound, C22H19BrN4O, are almost coplanar, their planes being inclined to one another by 2.08 (13)°. The dihedral angles formed by the mean plane of the fused ring system and the phenyl and benzene rings are 16.21 (4) and 82.84 (4)°, respectively. An intra­molecular N—H...N hydrogen bond is observed. In the crystal, mol­ecules form inversion dimers via pairs of C—H...O hydrogen bonds. π–π inter­actions, with centroid–centroid distances of 3.4916 (9) Å, connect the dimers into a three-dimensional network.
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