Axs smart apex 2 single crystal x ray diffractometer

¹H NMR (400 MHz), ¹³C NMR (100 MHz) and ¹⁹F NMR (376 MHz) spectra were recorded on Brucker Asend 400 spectrometers. HRMS was performed on Waters Micromass Q-TOF micro Synapt High Definition Mass Spectrometer. HPLC analysis using a chiral stationary phase was performed on Shimadzu or Dalian Elite (UV230+ UV/Vis Detector and P230P High Pressure Pump). CHIRALCEL OD-H or CHIRALPAK IC column was purchased from Daicel Chemical Industries, Ltd. Single-crystal X-ray diffraction data were recorded on Bruker-AXS SMART APEX II single-crystal X-ray diffractometer. See Supplementary Figs 1–62 for the NMR spectra and HPLC chromatograms, Supplementary Table 1 for the optimization of reaction, Supplementary Discussion for the mechanism studies and computational details and Supplementary Methods for the characterization data of compounds not listed in this part.

All ¹H NMR (400 MHz) and ¹³C NMR (100 MHz) spectra were recorded on Bruker spectrometers using CDCl₃ as solvent. Tetramethylsilane served as internal standard (δ = 0) for ¹H NMR, whereas CDCl₃ was used as internal standard (δ = 77.0) for ¹³C NMR. Chemical shifts were reported in parts per million with the following multiplicity: singlet, doublet, triplet, quartet, multiplet, and broad. HRMS was performed on IonSpec Fourier transform–ion cyclotron resonance or Waters Micromass Q-TOF micro synapt high definition mass spectrometry. Melting points were uncorrected. Single-crystal x-ray diffraction data (6i) were recorded on a Bruker-AXS SMART APEX II single-crystal x-ray diffractometer.
The solvents used for column chromatography were distilled before use. All reactions and manipulations were carried out in air using a flame- or oven-dried flask containing a magnetic stirring bar. 1-Sulfonyl–substituted triazoles and indoles were prepared according to the literature (103 (link), 104 (link)).

The morphology of samples was explored by a scanning electron microscope JEOL JSM-6360LV and a transmission electron microscope JEOL JEM-2100F. Powder X-ray diffraction (XRD) patterns were collected on a Rigaku TTR-III X-ray diffractometer with Cu Kα radiation (λ = 0.15406 nm). Bruker AXS Smart Apex II Single Crystal X-ray diffractometer was used to collect single crystal X-ray diffraction data. SHELX software was used to solve and refine the single crystral structure. Fourier transform infrared (FTIR) spectra of samples were recorded by a KBr pellet technique using a Thermo Fisher Nicolet 6700 spectrophotometer in the wavenumber range of 400–4000 cm⁻¹. The percentage composition of C, H, N elements present in samples was determined using an Elementar Vario EL III elemental analyzer. The contents of nickel in solid samples and reaction solutions were determined by ICP-AES instrument (ICP, Thermo Scientific, iCAP 7000). Thermogravimetric (TG) analysis was determined on Netzsch STA-449F3 TG/DTG instrument within a temperature range of 30 °C to 600 °C with a heating rate of 10 °C min⁻¹ under an argon atmosphere.