Methyl 1-(4-fluorobenzyl)-1H-indazole-3-carboxylate

The title compound was synthesized by nucleophilic substitution of the indazole N—H hydrogen atom of methyl 1H-indazole-3-carboxylate with 1-(bromomethyl)-4-fluorobenzene. In the crystal, some hydrogen-bond-like interactions are observed.


Structure description
Methyl 1-(4-fluorobenzyl)-1H-indazole-3-carboxylate is an intermediate compound of synthetic cannabinoids, a class of compounds with a high potential for abuse as psychoactive substances, acting as the agonist of the cannabinoid type 1 receptor (Longworth et al., 2017;Doi et al., 2018;Cannaert et al., 2020).The molecule is composed of two planar segments connected at a bond angle of 110.90 (8) � at C6.The indazole ring is nearly coplanar with the ester moiety, suggesting that the ester moiety is conjugated with the aromatic ring.Furthermore, the C3-C14 bond distance is 1.4790 (14) A ˚, which provides further evidence for the existence of conjugation (Fig. 1).The crystal packing of the title compound is displayed in Fig. 2. At the centre of the crystal, two weak hydrogenbond-like interactions (C13-H13� � �N2 ii and C6-H6A� � �O15 ii ) are formed between two adjacent molecules related by inversion (Fig. 2) [symmetry operator: (ii) À x, À y + 1, À z + 1].The hydrogen-donor molecule also acts as acceptor of the same interactions, creating inversion-related dimers.In the extended structure, there are four more nonclassical hydrogen-bond-like interactions and a weak C-H� � �� interaction is also observed (Table 1).

Synthesis and crystallization
The synthesis of methyl 1-(4-fluorobenzyl)-1H-indazole-3-carboxylate was described previously (Doi et al., 2018).In a microvial, the resulted compound was dissolved with ethyl acetate at a concentration of 3% (w/v).The microvial was left at room temperature for several months, resulting in the formation of several large rod shape crystals in the vial.

Refinement
Crystal, data collection and refinement details are presented in Table 2.

Figure 2
The crystal packing of the title compound.

Figure 1
Molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.

Special details
Geometry.All esds (except the esd in the dihedral angle between two l.s.planes) are estimated using the full covariance matrix.The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry.An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s.planes.

data reports data-2
IUCrData (2023).8, x230995 Refinement.All the H atoms were included using a riding model starting from calculated positions (aromatic C-H = 0.95 Å, methylene C-H = 0.99 Å, and alkyl C-H = 1.00 Å).The U iso (H) values were fixed at 1.2 times the equivalent U eq value of the parent C atoms (1.5 times for the methyl group).

Table 2
Experimental details.