Crystal structure of 2-[2-(2,5-di-chloro-benz-yloxy)-2-(furan-2-yl)eth-yl]-2H-indazole.

In the title compound, C20H16Cl2N2O2, the indazole ring system is approximately planar [maximum deviation = 0.033 (1) Å], its mean plane is oriented at dihedral angles of 25.04 (4) and 5.10 (4)° to the furan and benzene rings, respectively. In the crystal, pairs of C-Hind⋯Obo (ind = indazole and bo = benz-yloxy) hydrogen bonds link the mol-ecules into centrosymmetric dimers with graph-set motif R22(12). Weak C-H⋯π inter-actions is also observed. Aromatic π-π stacking between the benzene and the pyrazole rings from neighbouring mol-ecules [centroid-centroid distance = 3.8894 (7) Å] further consolidates the crystal packing.

Machine-learning-assisted materials discovery using failed experiments.

Inorganic-organic hybrid materials such as organically templated metal oxides, metal-organic frameworks (MOFs) and organohalide perovskites have been studied for decades, and hydrothermal and (non-aqueous) solvothermal syntheses have produced thousands of new materials that collectively contain nearly all the metals in the periodic table. Nevertheless, the formation of these compounds is not fully understood, and development of new compounds relies primarily on exploratory syntheses. Simulation- and data-driven approaches (promoted by efforts such as the Materials Genome Initiative) provide an alternative to experimental trial-and-error. Three major strategies are: simulation-based predictions of physical properties (for example, charge mobility, photovoltaic properties, gas adsorption capacity or lithium-ion intercalation) to identify promising target candidates for synthetic efforts; determination of the structure-property relationship from large bodies of experimental data, enabled by integration with high-throughput synthesis and measurement tools; and clustering on the basis of similar crystallographic structure (for example, zeolite structure classification or gas adsorption properties). Here we demonstrate an alternative approach that uses machine-learning algorithms trained on reaction data to predict reaction outcomes for the crystallization of templated vanadium selenites. We used information on 'dark' reactions--failed or unsuccessful hydrothermal syntheses--collected from archived laboratory notebooks from our laboratory, and added physicochemical property descriptions to the raw notebook information using cheminformatics techniques. We used the resulting data to train a machine-learning model to predict reaction success. When carrying out hydrothermal synthesis experiments using previously untested, commercially available organic building blocks, our machine-learning model outperformed traditional human strategies, and successfully predicted conditions for new organically templated inorganic product formation with a success rate of 89 per cent. Inverting the machine-learning model reveals new hypotheses regarding the conditions for successful product formation.

2-[2-(2,6-Di-chloro-benz-yloxy)-2-phenyl-eth-yl]-2H-indazole.

In the title compound, C22H18Cl2N2O, the indazole ring system is approximately planar [maximum deviation = 0.031 (2) Å], its mean plane is oriented at 3.17 (4) and 19.34 (4)° with respect to the phenyl and benzene rings. In the crystal, weak C-H⋯π inter-actions link the mol-ecules into supra-molecular chains running along the b-axis direction.

1-(Furan-2-yl)-2-(2H-indazol-2-yl)ethanone.

The asymmetric unit of the title compound, C13H10N2O2, contains two crystallographically independent mol-ecules (A and B). The indazole ring systems are approximately planar [maximum deviations = 0.0037 (15) and -0.0198 (15) Å], and their mean planes are oriented at 80.10 (5) and 65.97 (4)° with respect to the furan rings in mol-ecules A and B, respectively. In the crystal, pairs of C-H⋯N hydrogen bonds link the B mol-ecules, forming inversion dimers. These dimers are bridged by the A mol-ecules via C-H⋯O hydrogen bonds, forming sheets parallel to (011). There are also C-H⋯π inter-actions present, and π-π inter-actions between neighbouring furan and the indazole rings [centroid-centroid distance = 3.8708 (9) Å] of inversion-related mol-ecules, forming a three-dimensional structure.

1-{2-Benz-yloxy-2-[4-(morpholin-4-yl)phen-yl]eth-yl}-1H-benzimidazole.

In the title compound, C26H27N3O2, the morpholine ring adopts a chair conformation. The benzene and phenyl rings are inclined to the benzimidazole mean plane by 7.28 (6) and 61.45 (4)°, respectively. In the crystal, pairs of weak C-H⋯O hydrogen bonds link the mol-ecules into inversion dimers. These dimers are further connected via weak C-H⋯N hydrogen bonds. A weak C-H⋯π inter-action is also observed.

2-(2H-Indazol-2-yl)-1-phenyl-ethanone.

The asymmetric unit of the title compound, C(15)H(12)N(2)O, contains two independent mol-ecules with different conformations, the phenyl ring and indazole mean plane in the two mol-ecules forming dihedral angles of 50.82 (5) and 89.29 (6)°. In the crystal, weak C-H⋯O and C-H⋯N hydrogen bonds and C-H⋯π inter-actions consolidate the packing.

1-{2-(4-Chloro-benz-yloxy)-2-[4-(mor-pho-lin-4-yl)phen-yl]eth-yl}-1H-benzimidazole propan-2-ol monosolvate.

In the title compound, C26H26ClN3O2·C3H7OH, the benzimid-azole ring system is essentially planar [maximum deviation = -0.018 (2) Å] and its mean plane is oriented with respect to the two benzene rings at dihedral angles of 4.51 (6) and 56.16 (6)°, and the dihedral angle between the two benzene rings is 59.11 (7)°. The morpholine ring displays a chair conformation. The propan-2-ol solvent mol-ecule links with the benzimidazole ring via an O-H⋯N hydrogen bond. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into inversion dimers with an R 2 (2)(28) motif. π-π stacking occurs between the parallel chloro-benzene rings [centroid-centroid distance = 3.792 (1) Å]. Weak C-H⋯π inter-actions and short Cl⋯Cl [3.2037 (10) Å] contacts are also observed.