Supernova

Cupric bromide (CuBr₂) was purchased from Shanghai Xinbao Fine Chemical Factory (Shanghai, China). Tetrahydrofuran (THF) and acetonitrile (CH₃CN) were distilled over CaH₂ and stored under N₂ atomsphere. Compounds 1–7 were synthesized by following our previous reports [37 (link)–38 (link)].
The electrochemical properties of 1–7 were recorded on a RST 5000 electrochemical workstation at a scan rate of 50 mV s⁻¹, with glassy carbon discs as the working electrode, Pt wire as the counter electrode, and a SCE electrode as the reference electrode. The concentration was 5 × 10⁻⁴ mol L⁻¹ in CH₂Cl₂, and the supporting electrolyte was (n-Bu)₄N·PF₆ (0.1 mol L⁻¹). The measurement was performed at 20 °C after bubbling the solution with N₂ gas for 15 min.
The X-ray diffraction measurement was carried out on SuperNova (Agilent) type diffractometer. The crystal structure was solved by a direct method SIR2004 [61 (link)] and refined by a full-matrix least-squares method on F² by means of SHELXL-97 [62 ]. The X-ray powder diffraction (XRPD) pattern was recorded on X’Pert PRO (PANalytical). The temperature dependence of the magnetic susceptibility was measured on a SQUID magnetometer of Quantum Design MPMS-XL applying a magnetic field of 1 kOe. The data were corrected for core diamagnetism estimated from the sum of the Pascal constants [63 ].

Single crystals of 4r were C₁₉H₂₆ClN₅O₂ (CCDC 1437627 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44 1223 336033; E-mail: deposit@ccdc.cam.ac.uk), shown in Figure 1). A suitable crystal was selected an analyzed on a SuperNova, Dual, Cu at zero, Atlas diffractometer (Agilent, CA, USA) PW. The crystal was kept at 180.01(10) K during data collection. Using Olex2 [30 (link)], the structure was solved with the Superflip [31 (link)] structure solution program using Charge Flipping and refined with the Shelx [32 (link)] refinement package using Least Squares minimisation.

To observe the geometry of molecules and their interactions in the unit cell, we have crystalized the compound I (NDNA). Good-looking crystals were taken to the microscope for the final selection of sample for mounting on the diffractometer. The selected crystal was fixed over the tip of a thin glass fiber adsorbed in wax on a copper rod with a magnetic base. This holder was mounted on an Agilent SuperNova (dual source) Agilent Technologies Diffractometer, equipped with graphite-monochromatic Cu/Mo Kα radiation source for data collection. The data collection was accomplished using the CrysAlisPro software⁶³ at 296 K under Cu Kα radiation. The structure solution was performed and refined by full-matrix least-squares methods on F² using SHELXL-97,^{64 (link)} in-built with WinGX.^{65 (link)} All non-hydrogen atoms were refined anisotropically by full-matrix least-squares methods.^{64 (link)} Figures were drawn using PLATON⁶⁶ and ORTEP-3.^{67 (link)}All the aromatic hydrogen atoms were positioned geometrically and treated as riding atoms with C–H = 0.93 Å and U_iso (H) = 1.2 U_eq (C) carbon atoms. The N–H = 0.99(6) Å and O–H = 0.93(6) Å; the hydrogen atoms were located with the difference Fourier map and refined with U_iso (H) = 1.2 U_eq (N) and U_iso (H) = 1.5 U_eq (O), respectively. The CIF of the NDNA has been submitted to the Cambridge Crystallographic Data Centre (CCDC).

Single-crystal structure analysis of LDU-1 was performed at 293(2) K on an Agilent SuperNova diffractometer equipped with a copper micro-focus X-ray sources (λ = 1.54178 Å). The data were collected with an ω-scan mode in an arbitrary φ-angle. Data reduction was performed with the CrysAlisPro package, and an analytical absorption correction was performed. The structure was solved by direct methods and refined by full-matrix least-squares on F² with anisotropic displacement using the SHELXL software package [32 ]. The non-H atoms were treated anisotropically, whereas the aromatic and hydroxyl hydrogen atoms were placed in calculated ideal positions and refined as riding on their respective carbon or oxygen atoms. The structure was examined using the Addsym subroutine of PLATON to ensure that no additional symmetry could be applied to the models [33 ].