In the title molecule, C19H18N2O2, the orientation of the oxopropylidene substituent is largely determined by an intramolecular N—H...O hydrogen bond. In the crystal, C—H...O hydrogen bonds form zigzag chains, which are elaborated into sheets lying parallel to (101) by complementary C—H...π interactions. Comparisons to the structure of the triclinic modification are made.
In the title compound, C 9 H 8 ClN 3 O 2 , the orientation of the ethyl substituent is partly determined by an intramolecular C-HÁ Á ÁCl hydrogen bond. The indazole moiety is slightly folded with an angle of 0.70 (8) between the fiveand six-membered rings. In the crystal, molecules pack in layers parallel to [100] through C-HÁ Á Á(ring) and N . . . OÁ Á Á(ring) interactions.
The conformation of the title compound, C18H18N4O, is partly determined by an intramolecular N—H...O hydrogen bond that imposes planarity on the central aminoethylidene-3-methylpyrazol-5-one segment of the molecule. In the crystal, N—H...O hydrogen and N—H...N hydrogen bonds both form centrosymmetric dimers that encloseR22(18) rings. These, together with C—H...N and π–π stacking interactions between centrosymmetrically related pyrazalone rings, stack the molecules along theb-axis direction.
The asymmetric unit of the title compound, C 9 H 6 ClN 3 O 3 , contains one full molecule in a general position and a half molcule sitting on a crystallographic mirror plane. In the crystal, molecules form stacks extending along the b-axis direction through a combination of offset -stacking between indazole units and C-ClÁ Á Á (ring) interactions with the six-membered rings of the same units. Elaboration of the C-ClÁ Á Á (ring) interactions along the a-axis direction forms slabs of molecules parallel to [001]. The stacks are joined by a combination of C-HÁ Á ÁO and C-HÁ Á ÁN hydrogen bonds. Structure descriptionStudies of the structure and physicochemical properties of the indazole ring have been reviewed (Abbassi et al., 2014;Li et al., 2003;Lee et al., 2001). Indazole is a frequently found motif in drug substances with important biological activities, such as antimicrobial (Patel et al., 1999) and anti-inflammatory activities (Lin et al., 2008), and anticancer effects (Zhu et al., 2007). As a continuation of our studies of indazole derivatives (Mohamed Abdelahi et al., 2017a,b,c), we report the synthesis and structure of the title compound (Fig. 1).The asymmetric unit of the title compound consists of one molecule in a general position and a half molecule located on a crystallographic mirror plane at y = 1/4. The indazole portion of the former is planar to within 0.007 (1) Å (C16) and the dihedral angle between its mean plane and the mirror on which the latter lies is 4.82 (3) Å . For the overlay of the two independent molecules, values of 0.0130 and 0.0288 Å are obtained, respectively, for the r.m.s. deviation and the maximum deviation. In the crystal, molecules form stacks extending along the b-axis direction. One element of the stack is a dimer formed by pairwise head-to-tail offset -stacking interactions between the indazole (Table 1 and Fig. 4). As shown in Fig. 3, an R 3 3 (19) graph set is formed by two C-HÁ Á ÁO hydrogen bonds and one ClÁ Á ÁO interaction for the molecule in the general position. A corresponding set is formed with the molecule in the special position.
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