Direct Synthesis of a Copper(II) N-heterocyclic Carbene Complex in Air
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1 Supporting Information for Direct Synthesis of a Copper(II) N-heterocyclic Carbene Complex in Air Daniel J. O Hearn and Robert D. Singer* Atlantic Centre for Green Chemistry, Department of Chemistry, Saint Mary s University, Halifax, Canada, B3H 3C3. Table of Contents 1. Experimental S2 a. General Methods S2 b. 1,3-bis(pyridin-2-ylmethyl)-1H-imidazolium chloride (1) S2 c. Cu(1,3-bis(pyridin-2-ylmethyl)imidazolylidene)(MeOH)2(SiF6 2- ) (2) S3 2. NMR Spectra for 1 and 2 (Figures S1-S5) S4 3. IR Spectra of 1 and 2 (Figures S6 and S7) S7 4. Crystallographic Information for 2 and 3 (Tables S1-S6) S9 5. References S15
2 S2 1a. General Methods. Unless otherwise stated, all manipulations were preformed under ambient atmospheric conditions. All chemicals were purchased from Sigma Aldrich, Alfa Aeser, Oakwood Chemicals, Fisher Scientific, Caledon Laboratories, and were used without further purification. Deuterated NMR solvents were purchased from Cambridge Isotopes, and used without further purification. A Bruker 300 MHz Ultrashield spectrometer was used to obtain all NMR spectra. IR spectra were obtained using a Bruker ALPHA Platinum ATR fitted with a single reflection diamond. ESI-MS data were obtained using the Agilent 1100 LC/MSD Trap. All single crystal X-ray diffraction data were collected at 125 K using a Bruker Apex-II CCD diffractometer using a MoKα (λ = nm) radiation source. Data was integrated using Bruker ApexII. 1 SADABS-2008/1 was used for absorption correction. 2 Structure solutions were obtained with SHELXT using the intrinsic phasing method and structure refinement was carried out with SHELXL using the least squares method, both interfaced with Olex Hydrogen atoms were added on riding coordinates during refinement. All crystal structure images were generated using Olex 2, with thermal ellipsoids drawn at the 50% probability level. 1b. 1,3-bis(pyridin-2-ylmethyl)-1H-imidazolium chloride (1). 1,3-bis(pyridin-2-ylmethyl)-1H-imidazolium chloride, 1, was prepared using a modified method from the literature. 6-7 Imidazole (99%) (5.00 mmol/0.340 g), 2-(chloromethyl)pyridine hydrochloride (97%) (10.00 mmol/1.66 g) and sodium bicarbonate (15.10 mmol/1.30 g) were taken up in anhydrous ethanol (15 ml). The mixture was heated under reflux for 48 hours with stirring, then allowed to cool to room temperature. It was then filtered through Celite, and the solvent was removed by rotary evaporation. The brown residue was then taken up in a minimal amount of dichloromethane, then triturated with tetrahydrofuran (15-25 ml) resulting in a brown powder to precipitate. The supernatant was decanted, and the solid was washed with
3 S3 tetrahydrofuran (2x5 ml) and dried in vacuo. Yield: 1.46 g, 4.48 mmol, 90%. 1 H NMR (CDCl3, 300 MHz) δ (ppm) (s, 1H, NCHN), (m, 2H, pyridylh6), (m, 4H, HCCH, pyridylh5), (m, 2H, pyridylh3), (m, 2H, pyridylh4), 5.72 (s, 4H, NCH2C). 13 C{ 1 H} NMR (CDCl3, 300 MHz) δ (ppm) , , , , , , , FT- IR (ATR, cm -1 ) 3082 (m), 2945 (s), 1893 (w), 1800 (w), 1666 (w), 1564 (s), 1429 (s), 1164 (vs), 752 (vs). ESI-MS (+): Calcd for C15H15N4 m/z: Found m/z: c. Cu(1,3-bis(pyridin-2-ylmethyl)imidazolylidene)(MeOH)2(SiF6 2- ) (2). 1 (0.15 mmol/43 mg) was dissolved in methanol (2 ml) and added to a solution of copper(ii)hexafluorosilicate hydrate (0.15 mmol/31 mg) in methanol (4 ml) in a vial equipped with a magnetic stir bar. As the stirring proceeded, the solution took on a green colour that intensified with time. This green colour changed to blue, and the solution stirred overnight. After 17 hours, a dark blue precipitate had formed. The supernatant (green) was removed, and the dark blue solid was washed with methanol. The solid was found to be slightly soluble in methanol. Vapour diffusion of chloroform into the methanol solution for two weeks resulted in block shaped crystals suitable for single crystal X-ray diffraction. Yield: 28 mg, mmol, 36%. M.p C (decomp.) 1 H NMR (CDCl3, 300 MHz) δ (ppm) 9.50 (br), 8.55 (br), (m), (d), 5.60 (br) ESI-MS m/z [M] 2+ Calcd for C15H14CuN ; Found HRMS (ESI-TOF) m/z [M] 2+ Calcd for C15H14CuN ; Found
4 S4 2. NMR Spectra for 1 and 2 3/4/ Figure S1: 1 H NMR spectrum of 1 (CDCl3, 300 MHz). Assignments made with the assistance of COSY NMR Figure S2: Zoom in of the 1 H NMR spectrum of 1 (CDCl3, 300 MHz). Assignments made with the assistance of COSY NMR.
5 S5 2 3/ Figure S3: 13 C{ 1 H} NMR spectrum of 1 (CDCl3, 300 MHz). Assignments made with the assistance of HSQC NMR Figure S4: Zoom in of the 13 C{ 1 H} NMR spectrum of 1 (CDCl3, 300 MHz). Assignments made with the assistance of HSQC NMR.
6 S6 Figure S5: 1 H NMR spectrum of 2 ((CD3)2SO, 300 MHz).
7 S7 3. IR Spectra of 1 and 2 Figure S6: ATR-FTIR spectrum of 1.
8 Figure S7: ATR-FTIR spectrum of 2. S8
9 S9 4. Crystallographic Tables Table S1: Crystallographic information table for 2. Empirical formula C17H22CuF6N4O2Si Formula weight Temperature/K Crystal system orthorhombic Space group Pna21 a/å (4) b/å (2) c/å (4) α/ 90 β/ 90 γ/ 90 Volume/Å (9) Z 4 ρcalcg/cm μ/mm F(000) Crystal size/mm Radiation MoKα (λ = ) 2Θ range for data collection/ 5.02 to Index ranges -21 h 21, -10 k 10, -20 l 20 Reflections collected Independent reflections 5051 [Rint = , Rsigma = ] Data/restraints/parameters 5051/3/290 Goodness-of-fit on F Final R indexes [I>=2σ (I)] R1 = , wr2 = Final R indexes [all data] R1 = , wr2 = Largest diff. peak/hole / e Å /-0.42 Flack parameter 0.005(6)
10 S10 Table S2: Bond lengths from the crystal structure of 2. Atom Atom Length/Å Atom Atom Length/Å Cu1 F (19) N2 C (4) Cu1 O (2) N2 C (4) Cu1 O (3) N3 C (4) Cu1 N (3) N3 C (5) Cu1 N3' 2.057(3) N3' C5' 1.348(5) Cu1 C (3) N3' C6' 1.354(4) Si1 F (2) C2 C (5) Si1 F (2) C4 C (5) Si1 F (2) C4' C5' 1.518(4) Si1 F (2) C5 C (5) Si1 F (2) C5' C9' 1.382(5) Si1 F (2) C6 C (5) O1 C (4) C6' C7' 1.376(5) O2 C (4) C7 C (6) N1 C (4) C7' C8' 1.379(5) N1 C (4) C8 C (5) N1 C4' 1.468(4) C8' C9' 1.391(5) N2 C (4)
11 S11 Table S3: Bond angles from the crystal structure of 2. Atom Atom Atom Angle/ Atom Atom Atom Angle/ O1 Cu1 F (9) C1 N1 C (3) O1 Cu1 O (9) C1 N1 C4' 122.0(3) O1 Cu1 N (11) C3 N1 C4' 127.6(3) O1 Cu1 N3' 89.74(11) C1 N2 C (3) O2 Cu1 F (9) C1 N2 C (3) N3 Cu1 F (10) C2 N2 C (3) N3 Cu1 O (10) C5 N3 Cu (2) N3' Cu1 F (9) C6 N3 Cu (2) N3' Cu1 O (10) C6 N3 C (3) N3' Cu1 N (11) C5' N3' Cu (2) C1 Cu1 F (11) C5' N3' C6' 117.6(3) C1 Cu1 O (13) C6' N3' Cu (2) C1 Cu1 O (12) N1 C1 Cu (2) C1 Cu1 N (12) N2 C1 Cu (2) C1 Cu1 N3' 87.85(12) N2 C1 N (3) F1 Si1 F (13) C3 C2 N (3) F1 Si1 F (12) C2 C3 N (3) F1 Si1 F (11) N2 C4 C (3) F2 Si1 F (11) N1 C4' C5' 110.5(3) F2 Si1 F (11) N3 C5 C (3) F3 Si1 F (11) N3 C5 C (3) F3 Si1 F (11) C9 C5 C (3) F3 Si1 F (10) N3' C5' C4' 118.6(3) F3 Si1 F (12) N3' C5' C9' 122.2(3) F5 Si1 F (10) C9' C5' C4' 119.2(3) F6 Si1 F (12) N3 C6 C (4) F6 Si1 F (11) N3' C6' C7' 122.8(3) F6 Si1 F (11) C6 C7 C (4) F6 Si1 F (12) C6' C7' C8' 119.4(3) F6 Si1 F (10) C9 C8 C (3) Si1 F1 Cu (13) C7' C8' C9' 118.2(3) C10 O1 Cu (2) C8 C9 C (3) C11 O2 Cu (2) C5' C9' C8' 119.7(3)
12 S12 Table S4: Crystallographic information table for 3. Empirical formula C46H28Cl2Cu3D48F12N8O8S8Si2 Formula weight Temperature/K Crystal system triclinic Space group P-1 a/å (2) b/å (2) c/å (5) α/ (10) β/ (10) γ/ (10) Volume/Å (7) Z 1 ρcalcg/cm μ/mm F(000) Crystal size/mm Radiation MoKα (λ = ) 2Θ range for data collection/ to Index ranges -10 h 11, -12 k 13, -28 l 27 Reflections collected Independent reflections 7990 [Rint = , Rsigma = ] Data/restraints/parameters 7990/0/411 Goodness-of-fit on F Final R indexes [I>=2σ (I)] R1 = , wr2 = Final R indexes [all data] R1 = , wr2 = Largest diff. peak/hole / e Å /-0.40
13 S13 Table S5: Bond lengths from the crystal structure of 3. Atom Atom Length/Å Atom Atom Length/Å Cu1 Cl (5) Cu2 O (14) Cu1 O (15) Cu2 O (14) Cu1 N (17) Cu2 O (14) Cu1 N (17) Cu2 O (14) Cu1 C (19) S2 O (16) S1 O (16) S2 C (2) S1 C (2) S2 C (2) S1 C (2) S3 O (15) N1 C (3) S3 C (2) N1 C (3) S3 C (2) N1 C (3) S4 O (15) N2 C (2) S4 C (2) N2 C (2) S4 C (2) N2 C (2) C18 D18A N3 C (2) C18 D18B N3 C (2) C18 D18C N4 C (3) C19 D19A N4 C (3) C19 D19B C2 C (3) C19 D19C C4 C (3) C20 D20A C5 C (3) C20 D20B C6 C (3) C20 D20C C7 C (4) C21 D21A C8 C (4) C21 D21B C10 C (3) C21 D21C C11 C (3) C22 D22A C12 C (3) C22 D22B C13 C (3) C22 D22C C14 C (3) C23 D23A C16 D16A C23 D23B C16 D16B C23 D23C C16 D16C Si1 F (13) C17 D17A Si1 F (13) C17 D17B Si1 F (13) C17 D17C Si1 F (12) Cu2 O (15) Si1 F (13) Cu2 O (15) Si1 F (13)
14 S14 Table S6: Bond angles from the crystal structure of 3. Atom Atom Atom Angle/ Atom Atom Atom Angle/ Cl1 Cu1 O (4) O4 Cu2 O (6) N3 Cu1 Cl (5) O4 1 Cu2 O (6) N3 Cu1 O (6) O4 1 Cu2 O (6) N3 Cu1 N (6) O4 Cu2 O (6) N4 Cu1 Cl (5) O4 1 Cu2 O N4 Cu1 O (6) O2 S2 C (10) C1 Cu1 Cl (6) O2 S2 C (11) C1 Cu1 O (7) C18 S2 C (12) C1 Cu1 N (7) O3 S3 C (10) C1 Cu1 N (7) O3 S3 C (10) O1 S1 C (11) C21 S3 C (12) O1 S1 C (10) O4 S4 C (10) C17 S1 C (12) O4 S4 C (11) S1 O1 Cu (9) C22 S4 C (13) C1 N1 C (17) S2 O2 Cu (9) C1 N1 C (16) S3 O3 Cu (9) C2 N1 C (17) S4 O4 Cu (8) C1 N2 C (17) S2 C18 D18A C1 N2 C (16) S2 C18 D18B C3 N2 C (16) S2 C18 D18C C11 N3 Cu (13) D18A C18 D18B C12 N3 Cu (13) D18A C18 D18C C12 N3 C (17) D18B C18 D18C C5 N4 Cu (14) S2 C19 D19A C6 N4 Cu (14) S2 C19 D19B C6 N4 C (19) S2 C19 D19C N1 C1 Cu (15) D19A C19 D19B N1 C1 N (16) D19A C19 D19C N2 C1 Cu (14) D19B C19 D19C C3 C2 N (18) S3 C20 D20A C2 C3 N (18) S3 C20 D20B N1 C4 C (17) S3 C20 D20C N4 C5 C (18) D20A C20 D20B N4 C5 C (2) D20A C20 D20C C9 C5 C (2) D20B C20 D20C N4 C6 C (2) S3 C21 D21A C8 C7 C (2) S3 C21 D21B C7 C8 C (2) S3 C21 D21C C8 C9 C (2) D21A C21 D21B N2 C10 C (16) D21A C21 D21C N3 C11 C (17) D21B C21 D21C N3 C11 C (18) S4 C22 D22A C15 C11 C (17) S4 C22 D22B 109.5
15 S15 N3 C12 C (18) S4 C22 D22C C14 C13 C (19) D22A C22 D22B C13 C14 C (19) D22A C22 D22C C14 C15 C (19) D22B C22 D22C S1 C16 D16A S4 C23 D23A S1 C16 D16B S4 C23 D23B S1 C16 D16C S4 C23 D23C D16A C16 D16B D23A C23 D23B D16A C16 D16C D23A C23 D23C D16B C16 D16C D23B C23 D23C S1 C17 D17A F1 Si1 F (6) S1 C17 D17B F1 Si1 F (7) S1 C17 D17C F1 Si1 F (7) D17A C17 D17B F3 Si1 F (6) D17A C17 D17C F3 Si1 F (7) D17B C17 D17C F4 Si1 F (6) O2 1 Cu2 O F4 Si1 F (7) O3 1 Cu2 O (6) F4 Si1 F (6) O3 Cu2 O (6) F4 Si1 F (6) O3 1 Cu2 O (6) F4 Si1 F (6) O3 Cu2 O (6) F5 Si1 F (7) O3 Cu2 O F5 Si1 F (6) O4 Cu2 O (6) F5 Si1 F (6) O4 1 Cu2 O (6) F5 Si1 F (7) O4 Cu2 O (6) F6 Si1 F (6) O4 1 Cu2 O (6) 5. References (1) Bruker (2012). ApexII. Bruker AXS Inc., Madison, Wisconsin, USA. (2) G. M. Sheldrick, (1996). SADABS. Program for Empirical Absorption Correction. University of Gottingen, Germany. (3) Sheldrick, G.M. Acta Cryst. 2015, C71, 3-8. (4) Burla, M. C.; Caliandro, R.; Camalli, M.; Car-rozzini, B.; Cascarano, G. L.; De Caro, L.; Giacovazzo, C.; Polidori, G.; Siliqi, D.; Spagna, R. J. Appl. Cryst. 2007, 40, (5) Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., OLEX2: A complete structure solution, refinement and analysis program. J. Appl. Cryst. 2009, 42, (6) Magill, A. M.; McGuinness, D. S.; Cavell, K. J.; Britovsek, G. J. P.; Gibson, V. C.; White, A. J. P.; Williams, D. J.; White, A. H.; Skelton, B. W. J. Organomet. Chem. 2001, , (7) Zhanga, Z.; Yanga, Y.; Suna, H.; Cao, R. Inorg. Chim. Acta. 2015, 434,
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