Synthesis of New Heteroscorpionate Iridium(I) and Iridium(III) Complexes
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- Ενυώ Κόρακας
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1 Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2015 ELECTRONIC SUPPORTING INFORMATION For Synthesis of New Heteroscorpionate Iridium(I) and Iridium(III) Complexes Arián E. Roa, a Jesús Campos, a Margarita Paneque a, * Verónica Salazar, b, * Antonio Otero, c, * Agustín Lara-Sánchez, c, * Ana M. Rodríguez, c I. López-Solera c and M. Victoria Gómez c a Instituto de Investigaciones Químicas (IIQ), Departamento de Química Inorgánica, and Centro de Innovación en Química Avanzada (ORFEO-CINQA), CSIC and Universidad de Sevilla, Avenida Américo Vespucio 49, Sevilla, Spain. b Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Hidalgo, Pachuca, Hidalgo, México. c Departamento de Química Inorgánica, Orgánica y Bioquímica, and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universidad de Castilla-La Mancha, Ciudad Real, Spain. CORRESPONDING AUTHOR: paneque@iiq.csic.es, Salazar@uaeh.reduaeh.edu, Antonio.Otero@uclm.es and Agustin.Lara@uclm.es. CONTENTS 1. Crystallographic details of compound 9 S1
2 1. Crystallographic details of compound 9 S1
3 Crystal data C 32 H 48 Cl 6 Ir 2 N 4 F(000) = 2096 M r = D x = Mg m -3 Monoclinic, P2 1 /n Mo Kα radiation, λ = Å a = (2) Å Cell parameters from 9435 reflections b = (3) Å θ = c = (6) Å µ = 7.56 mm -1 β = (1) T = 173 K V = (14) Å 3 Prism, red Z = mm Data collection Bruker-Nonius X8kappa APEX II CCD area detector' diffractometer Radiation source: fine-focus sealed tube graphite R int = independent reflections 7693 reflections with I > 2σ(I) phi and ω scans with narrow frames θ max = 27.5, θ min = 2.1 Absorption correction: multi-scan SADABS, Bruker (2006). APEX 2. Version 2.1. Bruker Analytical X-ray Solutions, Madison, Wisconsin, USA. h = T min = 0.122, T max = k = measured reflections l = Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = 1.14 Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained 8597 reflections ( /σ) max = parameters ρ max = 1.63 e Å -3 0 restraints ρ min = e Å -3 w = 1/[σ 2 (F o 2 ) + (0.0167P) P] where P = (F o 2 + 2F c 2 )/3 S2
4 Geometric parameters (Å, º) Ir1 N (3) C17 H17B Ir1 N (3) C17 H17C Ir1 C (3) C18 H18A Ir1 C (4) C18 H18B Ir1 C (3) C18 H18C Ir1 C (4) C19 H19A Ir1 C (3) C19 H19B Ir1 Cl (9) C19 H19C N1 C (5) C20 H20A N1 N (4) C20 H20B N2 C (4) C20 H20C N2 C (4) C21 H21A N3 C (4) C21 H21B N3 N (4) C21 H21C N4 C (4) Ir2 C (4) N4 C (4) Ir2 C (4) C1 H1A Ir2 C (4) C1 H1B Ir2 C (4) C2 C (5) Ir2 C (4) C2 H2A Ir2 Cl (10) C2 H2B Ir2 Cl (9) C2 H2C Ir2 Cl (9) C3 C (5) C22 C (6) C4 C (5) C22 C (7) C4 H C22 C (7) C5 C (5) C23 C (6) C6 H6A C23 C (6) C6 H6B C24 C (6) C6 H6C C24 C (6) C7 C (5) C25 C (7) C7 H7A C25 C (7) C7 H7B C26 C (6) C7 H7C C27 H27A C8 C (5) C27 H27B C9 C (5) C27 H27C C9 H C28 H28A C10 C (5) C28 H28B C11 H11A C28 H28C C11 H11B C29 H29A C11 H11C C29 H29B S3
5 C12 C (6) C29 H29C C12 C (6) C30 H30A C12 C (6) C30 H30B C13 C (5) C30 H30C C13 C (6) C31 H31A C14 C (5) C31 H31B C14 C (5) C31 H31C C15 C (5) C32 Cl (6) C15 C (5) C32 Cl (5) C16 C (6) C32 H32A C17 H17A C32 H32B N1 Ir1 N (11) C12 C17 H17C N1 Ir1 C (13) H17A C17 H17C N3 Ir1 C (13) H17B C17 H17C N1 Ir1 C (14) C13 C18 H18A N3 Ir1 C (14) C13 C18 H18B C14 Ir1 C (14) H18A C18 H18B N1 Ir1 C (12) C13 C18 H18C N3 Ir1 C (12) H18A C18 H18C C14 Ir1 C (14) H18B C18 H18C C12 Ir1 C (13) C14 C19 H19A N1 Ir1 C (13) C14 C19 H19B N3 Ir1 C (14) H19A C19 H19B C14 Ir1 C (14) C14 C19 H19C C12 Ir1 C (17) H19A C19 H19C C15 Ir1 C (14) H19B C19 H19C N1 Ir1 C (13) C15 C20 H20A N3 Ir1 C (13) C15 C20 H20B C14 Ir1 C (14) H20A C20 H20B C12 Ir1 C (16) C15 C20 H20C C15 Ir1 C (13) H20A C20 H20C C13 Ir1 C (16) H20B C20 H20C N1 Ir1 Cl (8) C16 C21 H21A N3 Ir1 Cl (8) C16 C21 H21B C14 Ir1 Cl (10) H21A C21 H21B C12 Ir1 Cl (10) C16 C21 H21C C15 Ir1 Cl (10) H21A C21 H21C C13 Ir1 Cl (12) H21B C21 H21C C16 Ir1 Cl (11) C24 Ir2 C (17) C5 N1 N (3) C24 Ir2 C (16) C5 N1 Ir (2) C22 Ir2 C (19) S4
6 N2 N1 Ir (2) C24 Ir2 C (16) C3 N2 N (3) C22 Ir2 C (17) C3 N2 C (3) C26 Ir2 C (17) N1 N2 C (3) C24 Ir2 C (16) C10 N3 N (3) C22 Ir2 C (19) C10 N3 Ir (2) C26 Ir2 C (18) N4 N3 Ir (2) C23 Ir2 C (17) C8 N4 N (3) C24 Ir2 Cl (12) C8 N4 C (3) C22 Ir2 Cl (14) N3 N4 C (3) C26 Ir2 Cl (15) N2 C1 N (3) C23 Ir2 Cl (12) N2 C1 H1A C25 Ir2 Cl (13) N4 C1 H1A C24 Ir2 Cl (11) N2 C1 H1B C22 Ir2 Cl (14) N4 C1 H1B C26 Ir2 Cl (15) H1A C1 H1B C23 Ir2 Cl (12) C3 C2 H2A C25 Ir2 Cl (12) C3 C2 H2B Cl4 Ir2 Cl (4) H2A C2 H2B C24 Ir2 Cl (11) C3 C2 H2C C22 Ir2 Cl (13) H2A C2 H2C C26 Ir2 Cl (12) H2B C2 H2C C23 Ir2 Cl (12) N2 C3 C (3) C25 Ir2 Cl (12) N2 C3 C (3) Cl4 Ir2 Cl (4) C4 C3 C (3) Cl2 Ir2 Cl (3) C3 C4 C (3) C23 C22 C (4) C3 C4 H C23 C22 C (5) C5 C4 H C26 C22 C (5) N1 C5 C (3) C23 C22 Ir (2) N1 C5 C (3) C26 C22 Ir (2) C4 C5 C (3) C27 C22 Ir (3) C5 C6 H6A C24 C23 C (4) C5 C6 H6B C24 C23 C (4) H6A C6 H6B C22 C23 C (4) C5 C6 H6C C24 C23 Ir (2) H6A C6 H6C C22 C23 Ir (2) H6B C6 H6C C28 C23 Ir (3) C8 C7 H7A C23 C24 C (4) C8 C7 H7B C23 C24 C (4) H7A C7 H7B C25 C24 C (4) C8 C7 H7C C23 C24 Ir (2) H7A C7 H7C C25 C24 Ir (2) S5
7 H7B C7 H7C C29 C24 Ir (3) N4 C8 C (3) C26 C25 C (4) N4 C8 C (3) C26 C25 C (5) C9 C8 C (3) C24 C25 C (5) C8 C9 C (3) C26 C25 Ir (2) C8 C9 H C24 C25 Ir (2) C10 C9 H C30 C25 Ir (3) N3 C10 C (3) C25 C26 C (4) N3 C10 C (3) C25 C26 C (5) C9 C10 C (3) C22 C26 C (5) C10 C11 H11A C25 C26 Ir (2) C10 C11 H11B C22 C26 Ir (2) H11A C11 H11B C31 C26 Ir (3) C10 C11 H11C C22 C27 H27A H11A C11 H11C C22 C27 H27B H11B C11 H11C H27A C27 H27B C13 C12 C (3) C22 C27 H27C C13 C12 C (5) H27A C27 H27C C16 C12 C (5) H27B C27 H27C C13 C12 Ir (2) C23 C28 H28A C16 C12 Ir (2) C23 C28 H28B C17 C12 Ir (3) H28A C28 H28B C12 C13 C (3) C23 C28 H28C C12 C13 C (4) H28A C28 H28C C14 C13 C (4) H28B C28 H28C C12 C13 Ir (2) C24 C29 H29A C14 C13 Ir (2) C24 C29 H29B C18 C13 Ir (3) H29A C29 H29B C13 C14 C (3) C24 C29 H29C C13 C14 C (4) H29A C29 H29C C15 C14 C (3) H29B C29 H29C C13 C14 Ir (19) C25 C30 H30A C15 C14 Ir (18) C25 C30 H30B C19 C14 Ir (3) H30A C30 H30B C16 C15 C (3) C25 C30 H30C C16 C15 C (4) H30A C30 H30C C14 C15 C (3) H30B C30 H30C C16 C15 Ir (19) C26 C31 H31A C14 C15 Ir (18) C26 C31 H31B C20 C15 Ir (3) H31A C31 H31B C15 C16 C (3) C26 C31 H31C C15 C16 C (4) H31A C31 H31C S6
8 C12 C16 C (4) H31B C31 H31C C15 C16 Ir (19) Cl5 C32 Cl (3) C12 C16 Ir (2) Cl5 C32 H32A C21 C16 Ir (3) Cl6 C32 H32A C12 C17 H17A Cl5 C32 H32B C12 C17 H17B Cl6 C32 H32B H17A C17 H17B H32A C32 H32B N3 Ir1 N1 C (4) C14 C15 C16 C21 C14 Ir1 N1 C (4) C20 C15 C16 C21 S (4) -0.7 (6) C12 Ir1 N1 C (4) Ir1 C15 C16 C (4) C15 Ir1 N1 C (5) C14 C15 C16 Ir (2) C13 Ir1 N1 C (4) C20 C15 C16 Ir (4) C16 Ir1 N1 C (4) C13 C12 C16 C15 Cl1 Ir1 N1 C (4) C17 C12 C16 C (4) (4) N3 Ir1 N1 N (2) Ir1 C12 C16 C (2) C14 Ir1 N1 N (2) C13 C12 C16 C21 C12 Ir1 N1 N (3) C17 C12 C16 C (4) 5.1 (6) C15 Ir1 N1 N (3) Ir1 C12 C16 C (4) C13 Ir1 N1 N (3) C13 C12 C16 Ir (3) C16 Ir1 N1 N (3) C17 C12 C16 Ir (4) Cl1 Ir1 N1 N (2) N1 Ir1 C16 C (2) C5 N1 N2 C3 0.6 (4) N3 Ir1 C16 C (2) Ir1 N1 N2 C (2) C14 Ir1 C16 C (2) C5 N1 N2 C (3) C12 Ir1 C16 C (3) Ir1 N1 N2 C1 8.1 (4) C13 Ir1 C16 C (2) N1 Ir1 N3 C (3) Cl1 Ir1 C16 C (3) C14 Ir1 N3 C (5) N1 Ir1 C16 C (3) C12 Ir1 N3 C (3) N3 Ir1 C16 C (2) C15 Ir1 N3 C (4) C14 Ir1 C16 C (2) C13 Ir1 N3 C (4) C15 Ir1 C16 C (3) C16 Ir1 N3 C (4) C13 Ir1 C16 C (2) Cl1 Ir1 N3 C (3) Cl1 Ir1 C16 C (18) N1 Ir1 N3 N (2) N1 Ir1 C16 C (5) C14 Ir1 N3 N (3) N3 Ir1 C16 C (4) C12 Ir1 N3 N (3) C14 Ir1 C16 C (5) C15 Ir1 N3 N (2) C12 Ir1 C16 C (5) C13 Ir1 N3 N (3) C15 Ir1 C16 C (5)
9 C16 Ir1 N3 N (3) C13 Ir1 C16 C (5) Cl1 Ir1 N3 N (2) Cl1 Ir1 C16 C (4) C10 N3 N4 C8-0.3 (4) C24 Ir2 C22 C (3) Ir1 N3 N4 C (2) C26 Ir2 C22 C (4) C10 N3 N4 C (3) C25 Ir2 C22 C (3) Ir1 N3 N4 C (4) Cl4 Ir2 C22 C (4) C3 N2 C1 N (3) Cl2 Ir2 C22 C (3) N1 N2 C1 N (4) Cl3 Ir2 C22 C (2) C8 N4 C1 N (3) C24 Ir2 C22 C (3) N3 N4 C1 N (4) C23 Ir2 C22 C (4) N1 N2 C3 C4-1.0 (4) C25 Ir2 C22 C (3) C1 N2 C3 C (3) Cl4 Ir2 C22 C (5) N1 N2 C3 C (3) Cl2 Ir2 C22 C (2) C1 N2 C3 C2-7.9 (5) Cl3 Ir2 C22 C (2) N2 C3 C4 C5 1.0 (4) C24 Ir2 C22 C (6) C2 C3 C4 C (4) C26 Ir2 C22 C (6) N2 N1 C5 C4 0.0 (4) C23 Ir2 C22 C (6) Ir1 N1 C5 C (3) C25 Ir2 C22 C (6) N2 N1 C5 C (4) Cl4 Ir2 C22 C (4) Ir1 N1 C5 C6-2.7 (6) Cl2 Ir2 C22 C (5) C3 C4 C5 N1-0.7 (5) Cl3 Ir2 C22 C (5) C3 C4 C5 C (4) C26 C22 C23 C24 N3 N4 C8 C9 0.5 (4) C27 C22 C23 C (4) (4) C1 N4 C8 C (3) Ir2 C22 C23 C (3) N3 N4 C8 C (3) C26 C22 C23 C28 C1 N4 C8 C7 8.9 (5) C27 C22 C23 C (4) -0.3 (7) N4 C8 C9 C (4) Ir2 C22 C23 C (4) C7 C8 C9 C (4) C26 C22 C23 Ir (3) N4 N3 C10 C9 0.0 (4) C27 C22 C23 Ir (5) Ir1 N3 C10 C (2) C22 Ir2 C23 C (4) N4 N3 C10 C (4) C26 Ir2 C23 C (3) Ir1 N3 C10 C (6) C25 Ir2 C23 C (2) C8 C9 C10 N3 0.3 (4) Cl4 Ir2 C23 C (3) C8 C9 C10 C (4) Cl2 Ir2 C23 C (2) N1 Ir1 C12 C (2) Cl3 Ir2 C23 C (19) N3 Ir1 C12 C (2) C24 Ir2 C23 C (4) C14 Ir1 C12 C (2) C26 Ir2 C23 C (3) C15 Ir1 C12 C (2) C25 Ir2 C23 C (3) C16 Ir1 C12 C (3) Cl4 Ir2 C23 C (2) S8
10 Cl1 Ir1 C12 C (4) Cl2 Ir2 C23 C (3) N1 Ir1 C12 C (2) Cl3 Ir2 C23 C (3) N3 Ir1 C12 C (2) C24 Ir2 C23 C (5) C14 Ir1 C12 C (2) C22 Ir2 C23 C (5) C15 Ir1 C12 C (2) C26 Ir2 C23 C (5) C13 Ir1 C12 C (3) C25 Ir2 C23 C (5) Cl1 Ir1 C12 C (4) Cl4 Ir2 C23 C (4) N1 Ir1 C12 C (5) Cl2 Ir2 C23 C (4) N3 Ir1 C12 C (5) Cl3 Ir2 C23 C (4) C14 Ir1 C12 C (6) C15 Ir1 C12 C (6) C22 C23 C24 C25 C28 C23 C24 C (4) (4) C13 Ir1 C12 C (6) Ir2 C23 C24 C (2) C16 Ir1 C12 C (6) C22 C23 C24 C29 Cl1 Ir1 C12 C (4) C28 C23 C24 C29 C16 C12 C13 C14 C17 C12 C13 C (4) -1.4 (6) 3.4 (4) Ir2 C23 C24 C (4) (4) C22 C23 C24 Ir (3) Ir1 C12 C13 C (3) C28 C23 C24 Ir (4) C16 C12 C13 C18 C17 C12 C13 C (4) C22 Ir2 C24 C (3) -6.0 (6) C26 Ir2 C24 C (3) Ir1 C12 C13 C (4) C25 Ir2 C24 C (3) C16 C12 C13 Ir (2) Cl4 Ir2 C24 C (2) C17 C12 C13 Ir (4) Cl2 Ir2 C24 C (2) N1 Ir1 C13 C (2) Cl3 Ir2 C24 C (4) N3 Ir1 C13 C (3) C22 Ir2 C24 C (3) C14 Ir1 C13 C (3) C26 Ir2 C24 C (3) C15 Ir1 C13 C (2) C23 Ir2 C24 C (3) C16 Ir1 C13 C (2) Cl4 Ir2 C24 C (2) Cl1 Ir1 C13 C (18) Cl2 Ir2 C24 C (2) N1 Ir1 C13 C (2) Cl3 Ir2 C24 C (5) N3 Ir1 C13 C (2) C22 Ir2 C24 C (5) C12 Ir1 C13 C (3) C26 Ir2 C24 C (5) C15 Ir1 C13 C (2) C23 Ir2 C24 C (5) C16 Ir1 C13 C (2) C25 Ir2 C24 C (5) Cl1 Ir1 C13 C (3) Cl4 Ir2 C24 C (4) N1 Ir1 C13 C (5) Cl2 Ir2 C24 C (4) N3 Ir1 C13 C (5) Cl3 Ir2 C24 C (3) S9
11 C14 Ir1 C13 C (6) C12 Ir1 C13 C (5) C23 C24 C25 C26 C29 C24 C25 C (4) (4) C15 Ir1 C13 C (5) Ir2 C24 C25 C (3) C16 Ir1 C13 C (5) C23 C24 C25 C30 Cl1 Ir1 C13 C (5) C29 C24 C25 C30 C12 C13 C14 C15 C18 C13 C14 C (4) 2.5 (6) -2.3 (4) Ir2 C24 C25 C (4) (4) C23 C24 C25 Ir (2) Ir1 C13 C14 C (2) C29 C24 C25 Ir (4) C12 C13 C14 C19 C18 C13 C14 C (4) C24 Ir2 C25 C (4) 1.4 (6) C22 Ir2 C25 C (3) Ir1 C13 C14 C (4) C23 Ir2 C25 C (3) C12 C13 C14 Ir (3) Cl4 Ir2 C25 C (3) C18 C13 C14 Ir (4) Cl2 Ir2 C25 C (3) N1 Ir1 C14 C (3) Cl3 Ir2 C25 C (3) N3 Ir1 C14 C (3) C22 Ir2 C25 C (3) C12 Ir1 C14 C (2) C26 Ir2 C25 C (4) C15 Ir1 C14 C (3) C23 Ir2 C25 C (2) C16 Ir1 C14 C (3) Cl4 Ir2 C25 C (2) Cl1 Ir1 C14 C (2) Cl2 Ir2 C25 C (4) N1 Ir1 C14 C (18) Cl3 Ir2 C25 C (2) N3 Ir1 C14 C (4) C24 Ir2 C25 C (6) C12 Ir1 C14 C (2) C22 Ir2 C25 C (5) C13 Ir1 C14 C (3) C26 Ir2 C25 C (6) C16 Ir1 C14 C (2) C23 Ir2 C25 C (5) Cl1 Ir1 C14 C (19) Cl4 Ir2 C25 C (5) N1 Ir1 C14 C (4) Cl2 Ir2 C25 C (4) N3 Ir1 C14 C (4) Cl3 Ir2 C25 C (5) C12 Ir1 C14 C (4) C15 Ir1 C14 C (4) C24 C25 C26 C22 C30 C25 C26 C (4) (4) C13 Ir1 C14 C (5) Ir2 C25 C26 C (3) C16 Ir1 C14 C (4) C24 C25 C26 C31 Cl1 Ir1 C14 C (3) C30 C25 C26 C31 C13 C14 C15 C (4) -2.5 (7) 0.2 (4) Ir2 C25 C26 C (4) S10
12 C19 C14 C15 C (3) C24 C25 C26 Ir (3) Ir1 C14 C15 C (2) C30 C25 C26 Ir (4) C13 C14 C15 C20 C19 C14 C15 C (3) C23 C22 C26 C (6) C27 C22 C26 C (4) (4) Ir1 C14 C15 C (4) Ir2 C22 C26 C (3) C13 C14 C15 Ir (2) C19 C14 C15 Ir (4) C23 C22 C26 C31 C27 C22 C26 C (4) 1.8 (7) N1 Ir1 C15 C (3) Ir2 C22 C26 C (4) N3 Ir1 C15 C (3) C23 C22 C26 Ir (3) C14 Ir1 C15 C (3) C27 C22 C26 Ir (5) C12 Ir1 C15 C (2) C24 Ir2 C26 C (3) C13 Ir1 C15 C (3) C22 Ir2 C26 C (4) Cl1 Ir1 C15 C (2) C23 Ir2 C26 C (3) N1 Ir1 C15 C (4) Cl4 Ir2 C26 C (3) N3 Ir1 C15 C (19) Cl2 Ir2 C26 C (3) C12 Ir1 C15 C (2) Cl3 Ir2 C26 C (2) C13 Ir1 C15 C (2) C24 Ir2 C26 C (3) C16 Ir1 C15 C (3) C23 Ir2 C26 C (3) Cl1 Ir1 C15 C (19) C25 Ir2 C26 C (4) N1 Ir1 C15 C (4) Cl4 Ir2 C26 C (2) N3 Ir1 C15 C (4) Cl2 Ir2 C26 C (4) C14 Ir1 C15 C (4) Cl3 Ir2 C26 C (2) C12 Ir1 C15 C (4) C24 Ir2 C26 C (6) C13 Ir1 C15 C (4) C22 Ir2 C26 C (7) C16 Ir1 C15 C (4) C23 Ir2 C26 C (6) Cl1 Ir1 C15 C (3) C25 Ir2 C26 C (7) C14 C15 C16 C12 C20 C15 C16 C (4) Cl4 Ir2 C26 C (6) (4) Cl2 Ir2 C26 C (5) Ir1 C15 C16 C (2) Cl3 Ir2 C26 C (6) S11
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chlorostibine Iou-Sheng Ke and François P. Gabbai Department of Chemistry, Texas A&M University, College Station, TX
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SUPPLEMENTARY MATERIAL. A Facile and Convenient Approach for the Synthesis of Novel Sesamol-Oxazine and Quinoline- Oxazine Hybrids
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