Single Crystal X-Ray Structure Determination of Compounds 8a, 8b and 11a
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- Δορκάς Αγγελόπουλος
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1 Single Crystal X-Ray Structure Determination of Compounds 8a, 8b and 11a General: Preliminary examination and data collection were carried out on an area detecting system (Kappa-CCD; Nonius) using graphite-monochromated Mo K α radiation (λ = Å) with an Oxford Cryosystems cooling system at the window of a sealed fine-focus X-ray tube. The reflections were integrated. Raw data were corrected for Lorentz, polarization, decay, and absorption effects. The absorption correction was applied using SADABS. I After merging, the independent reflections were used for all calculations. The structure was solved by a combination of direct methods II and difference Fourier syntheses. III All non-hydrogen atom positions were refined with anisotropic displacement parameters. Hydrogen atoms were placed in ideal positions using the SHELXL riding model. Full-matrix least-squares refinements were carried out by minimizing Σw(F 2 o - F 2 c ) 2 with the SHELXL-97 weighting scheme and stopped at shift/err < Neutral-atom scattering factors for all atoms and anomalous dispersion corrections for the non-hydrogen atoms were taken from ref V. All calculations were performed with the programs COLLECT, VI DIRAX, VII EVALCCD, VIII SIR92, II SADABS, I PLATON, IX and the SHELXL-97 package. III,IV For visualization Mercury X and PLATON IX and for the preparation of supporting material ENCIFER XI and PLATON IX were used. [I] Sheldrick, G. M. SADABS, Version 2.10; University of Göttingen, Göttingen, Germany, [II] Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli M. "SIR92", J. Appl. Cryst. 1994, 27, [III] Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112. [IV] Sheldrick, G. M. "SHELXL-97", University of Göttingen, Göttingen, Germany, (1998). [V] International Tables for Crystallography, Vol. C, Tables (pp ), (pp ), and (pp ), Wilson, A. J. C., Ed., Kluwer Academic Publishers, Dordrecht, The Netherlands, [VI] Hooft, R. W. W. COLLECT Data Collection Software for Nonius-Kappa CCD; Nonius BV., Delft, The Netherlands, [VII] Duisenberg, A. J. M. J. Appl. Crystallogr. 1992, 25, 92. [VIII] Duisenberg, A. J. M.; Kroon-Batenburg, L. M. J.; Schreurs, A. M. M., J. Appl. Crystallogr. 2003, 36, 220. [IX] Spek, A. L. "PLATON", A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands, (2010). [X] Macrae, C. F.; Bruno, I. J.; Chisholm, J. A.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Rodriguez-Monge, L.; Taylor, R.; van de Streek, J.; Wood, P. A. J. Appl. Crystallogr. 2008, 41, 466. [XI] Allen, F. H.; Johnson, O.; Shields, G. P.; Smith, B. R.; Towler, M. J. Appl. Crystallogr. 2004, 37, 335. S1
2 Compound 8a Table S1 - Crystal Data and Details of the Structure Determination for: Compound 8a Crystal Data Formula C14 H14 Br2 N4 Pd Formula Weight Crystal System Orthorhombic Space group Pna21 (No. 33) a, b, c [Angstrom] (9) 9.508(2) (17) V [Ang**3] (4) Z 4 D(calc) [g/cm**3] Mu(MoKa) [ /mm ] F(000) 968 Crystal Size [mm] 0.20 x 0.20 x 0.20 Data Collection Temperature (K) 198 Radiation [Angstrom] MoK Theta Min-Max [Deg] 4.8, 25.4 Dataset -14: 14 ; -11: 11 ; -16: 16 Tot., Uniq. Data, R(int) 11505, 3005, Observed data [I > 2.0 sigma(i)] 2748 Refinement Nref, Npar 3005, 192 R, wr2, S , , 1.06 w = 1/[\s^2^(Fo^2^)+(0.0000P)^2^] where P=(Fo^2^+2Fc^2^)/3 Max. and Av. Shift/Error 0.01, 0.00 Flack x 0.025(7) Min. and Max. Resd. Dens. [e/ang^3] -0.33, 0.33 Table S2 - Bond Distances (Angstrom) for: Compound 8a Pd1 -Br (6) C5 -C (5) Pd1 -Br (8) C6 -C (6) Pd1 -C (4) C7 -C (5) Pd1 -C (3) C8 -C (5) N1 -C (4) C11 -C (6) N1 -C (4) C2 -H N1 -C (5) C3 -H N2 -C (5) C5 -H N2 -C (4) C6 -H N2 -C (4) C7 -H N3 -C (4) C8 -H N3 -C (4) C11 -H N3 -C (5) C12 -H N4 -C (4) C13 -H13A N4 -C (5) C13 -H13B N4 -C (5) C13 -H13C C2 -C (5) C14 -H14A C4 -C (5) C14 -H14B C4 -C (5) C14 -H14C S2
3 Table S3 - Bond Angles (Degrees) for: Compound 8a Br1 -Pd1 -Br (2) Pd1 -C10 -N (2) Br1 -Pd1 -C (10) Pd1 -C10 -N (3) Br1 -Pd1 -C (13) N3 -C10 -N (2) Br2 -Pd1 -C (8) N4 -C11 -C (3) Br2 -Pd1 -C (12) N3 -C12 -C (3) C1 -Pd1 -C (15) N1 -C2 -H C1 -N1 -C (3) C3 -C2 -H C1 -N1 -C (3) N2 -C3 -H C2 -N1 -C (3) C2 -C3 -H C1 -N2 -C (3) C4 -C5 -H C1 -N2 -C (3) C6 -C5 -H C3 -N2 -C (3) C5 -C6 -H C9 -N3 -C (3) C7 -C6 -H C9 -N3 -C (3) C6 -C7 -H C10 -N3 -C (3) C8 -C7 -H C10 -N4 -C (3) C7 -C8 -H C10 -N4 -C (3) C9 -C8 -H C11 -N4 -C (3) N4 -C11 -H Pd1 -C1 -N (3) C12 -C11 -H Pd1 -C1 -N (2) N3 -C12 -H N1 -C1 -N (3) C11 -C12 -H N1 -C2 -C (3) N1 -C13 -H13A N2 -C3 -C (3) N1 -C13 -H13B N2 -C4 -C (3) N1 -C13 -H13C N2 -C4 -C (3) H13A -C13 -H13B C5 -C4 -C (3) H13A -C13 -H13C C4 -C5 -C (4) H13B -C13 -H13C C5 -C6 -C (4) N4 -C14 -H14A C6 -C7 -C (4) N4 -C14 -H14B C7 -C8 -C (4) N4 -C14 -H14C N3 -C9 -C (3) H14A -C14 -H14B N3 -C9 -C (3) H14A -C14 -H14C C4 -C9 -C (3) H14B -C14 -H14C Figure F1 Ortep drawing with 50% ellipsoids for: Compound 8a S3
4 Compound 8b Table S4 - Crystal Data and Details of the Structure Determination for: Compound 8b Crystal Data Formula C22 H18 Br2 N4 Pd, 2(C2 H3 N) Formula Weight Crystal System Triclinic Space group P-1 (No. 2) a, b, c [Angstrom] (12) (2) (7) alpha, beta, gamma [deg] (9) (6) (15) V [Ang**3] (3) Z 2 D(calc) [g/cm**3] Mu(MoKa) [ /mm ] F(000) 676 Crystal Size [mm] 0.19 x 0.19 x 0.33 Data Collection Temperature (K) 198 Radiation [Angstrom] MoK Theta Min-Max [Deg] 2.7, 26.4 Dataset -12: 11 ; -13: 13 ; 0: 17 Tot., Uniq. Data, R(int) 5686, 5686, Observed data [I > 2.0 sigma(i)] 4437 Refinement Nref, Npar 5686, 320 R, wr2, S , , 1.05 w = 1/[\s^2^(Fo^2^)+(0.0203P)^2^ P] where P=(Fo^2^+2Fc^2^)/3 Max. and Av. Shift/Error 0.00, 0.00 Min. and Max. Resd. Dens. [e/ang^3] -0.54, 0.50 The unit cell contains 1 disordered acetonitrile molecule which has been treated as a diffuse contribution to the overall scattering without specific atom positions by SQUEEZE/PLATON. IX Table S5 - Bond Distances (Angstrom) for: Compound 8b Pd1 -Br (6) C14 -C (4) Pd1 -Br (6) C15 -C (4) Pd1 -C (3) C17 -C (6) Pd1 -C (3) C18 -C (6) N1 -C (3) C19 -C (5) N1 -C (4) C5 -H N1 -C (4) C6 -H N2 -C (4) C7 -H N2 -C (4) C8 -H N2 -C (3) C13 -H N3 -C (4) C14 -H N3 -C (4) C15 -H N3 -C (4) C16 -H N4 -C (4) C17 -H N4 -C (4) C18 -H N4 -C (5) C19 -H N5 -C (5) C20 -H N6 -C (6) C21 -H21C C2 -C (4) C21 -H21A S4
5 C2 -C (4) C21 -H21B C3 -C (4) C22 -H22C C4 -C (4) C22 -H22A C4 -C (4) C22 -H22B C5 -C (4) C23 -C (6) C6 -C (4) C23 -H23B C7 -C (4) C23 -H23C C8 -C (4) C23 -H23A C11 -C (5) C25 -C (6) C11 -C (5) C25 -H25A C12 -C (5) C25 -H25B C13 -C (4) C25 -H25C Table S6 - Bond Angles (Degrees) for: Compound 8b Br1 -Pd1 -Br (2) C18 -C19 -C (4) Br1 -Pd1 -C (9) C12 -C20 -C (3) Br1 -Pd1 -C (9) C4 -C5 -H Br2 -Pd1 -C (10) C6 -C5 -H Br2 -Pd1 -C (9) C5 -C6 -H C1 -Pd1 -C (13) C7 -C6 -H C1 -N1 -C (2) C6 -C7 -H C1 -N1 -C (2) C8 -C7 -H C2 -N1 -C (2) C7 -C8 -H C1 -N2 -C (2) C9 -C8 -H C1 -N2 -C (2) C2 -C13 -H C3 -N2 -C (2) C14 -C13 -H C9 -N3 -C (2) C13 -C14 -H C9 -N3 -C (3) C15 -C14 -H C10 -N3 -C (3) C14 -C15 -H C10 -N4 -C (3) C16 -C15 -H C10 -N4 -C (3) C3 -C16 -H C11 -N4 -C (2) C15 -C16 -H Pd1 -C1 -N (2) C11 -C17 -H Pd1 -C1 -N (19) C18 -C17 -H N1 -C1 -N (2) C17 -C18 -H N1 -C2 -C (2) C19 -C18 -H N1 -C2 -C (3) C18 -C19 -H C3 -C2 -C (3) C20 -C19 -H N2 -C3 -C (2) C12 -C20 -H N2 -C3 -C (2) C19 -C20 -H C2 -C3 -C (3) N1 -C21 -H21A N2 -C4 -C (3) N1 -C21 -H21B N2 -C4 -C (3) N1 -C21 -H21C C5 -C4 -C (3) H21A -C21 -H21B C4 -C5 -C (3) H21A -C21 -H21C C5 -C6 -C (3) H21B -C21 -H21C C6 -C7 -C (3) N4 -C22 -H22A C7 -C8 -C (3) N4 -C22 -H22B N3 -C9 -C (2) N4 -C22 -H22C N3 -C9 -C (3) H22A -C22 -H22B C4 -C9 -C (3) H22A -C22 -H22C Pd1 -C10 -N (2) H22B -C22 -H22C Pd1 -C10 -N (2) N5 -C24 -C (4) N3 -C10 -N (3) C24 -C23 -H23A N4 -C11 -C (3) C24 -C23 -H23B N4 -C11 -C (3) C24 -C23 -H23C C12 -C11 -C (3) H23A -C23 -H23B N3 -C12 -C (3) H23A -C23 -H23C N3 -C12 -C (3) H23B -C23 -H23C C11 -C12 -C (3) N6 -C26 -C (5) S5
6 C2 -C13 -C (3) C26 -C25 -H25A C13 -C14 -C (3) C26 -C25 -H25B C14 -C15 -C (3) C26 -C25 -H25C C3 -C16 -C (3) H25A -C25 -H25B C11 -C17 -C (3) H25A -C25 -H25C C17 -C18 -C (3) H25B -C25 -H25C Figure F2 Ortep drawing with 50% ellipsoids for: Compound 8b Compound 11a Table S7 - Crystal Data and Details of the Structure Determination for: Compound 11a Crystal Data Formula 2(C26 H21 Br4 N4 Pd), 3(C H2 Cl2) Formula Weight Crystal System Orthorhombic Space group Pbcn (No. 60) a, b, c [Angstrom] (2) (5) (4) V [Ang**3] 6351(2) Z 4 D(calc) [g/cm**3] Mu(MoKa) [ /mm ] F(000) 3632 Crystal Size [mm] 0.15 x 0.20 x 0.20 Data Collection Temperature (K) 198 Radiation [Angstrom] MoK Theta Min-Max [Deg] 4.8, 26.4 Dataset -26: 26 ; -23: 23 ; -19: 20 Tot., Uniq. Data, R(int) , 6472, Observed data [I > 2.0 sigma(i)] 4896 Refinement Nref, Npar 6472, 357 R, wr2, S , , 1.09 w = 1/[\s^2^(Fo^2^)+(0.0056P)^2^ P] where P=(Fo^2^+2Fc^2^)/ Max. and Av. Shift/Error 0.00, 0.00 Min. and Max. Resd. Dens. [e/ang^3] -0.72, 0.69 S6
7 Table S8 - Bond Distances (Angstrom) for: Compound 11a Pd1 -Br (8) C17 -C (8) Pd1 -Br (8) C18 -C (7) Pd1 -C (3) C20 -C (5) Pd1 -C (3) C21 -C (5) Br3 -C (4) C21 -C (6) Br4 -C (4) C22 -C (8) Cl1 -C (10) C23 -C (10) Cl2 -C (8) C24 -C (11) Cl3 -C (5) C25 -C (8) N1 -C (4) C2 -H N1 -C (4) C3 -H N1 -C (4) C5 -H N2 -C (4) C8 -H N2 -C (4) C11 -H N2 -C (4) C12 -H N3 -C (5) C13 -H13B N3 -C (4) C13 -H13A N3 -C (5) C15 -H N4 -C (4) C16 -H N4 -C (5) C17 -H17B N4 -C (5) C17 -H17A C2 -C (5) C18 -H C4 -C (5) C19 -H C4 -C (5) C20 -H20B C5 -C (5) C20 -H20A C6 -C (5) C22 -H C7 -C (5) C23 -H C8 -C (5) C24 -H C11 -C (5) C25 -H C13 -C (5) C26 -H C14 -C (6) C27 -H27A C14 -C (6) C27 -H27B C15 -C (8) C28 -H28A C16 -C (9) C28 -H28B Table S9 - Bond Angles (Degrees) for: Compound 11a Br1 -Pd1 -Br (2) C22 -C23 -C (5) Br1 -Pd1 -C (10) C23 -C24 -C (6) Br1 -Pd1 -C (10) C24 -C25 -C (6) Br2 -Pd1 -C (9) C21 -C26 -C (5) Br2 -Pd1 -C (9) N1 -C2 -H C1 -Pd1 -C (13) C3 -C2 -H C1 -N1 -C (3) N2 -C3 -H C1 -N1 -C (3) C2 -C3 -H C2 -N1 -C (3) C4 -C5 -H C1 -N2 -C (3) C6 -C5 -H C1 -N2 -C (3) C7 -C8 -H C3 -N2 -C (3) C9 -C8 -H C9 -N3 -C (3) N4 -C11 -H C9 -N3 -C (3) C12 -C11 -H C10 -N3 -C (3) N3 -C12 -H C10 -N4 -C (3) C11 -C12 -H C10 -N4 -C (3) N1 -C13 -H13A C11 -N4 -C (3) N1 -C13 -H13B Pd1 -C1 -N (2) C14 -C13 -H13A Pd1 -C1 -N (2) C14 -C13 -H13B N1 -C1 -N (3) H13A -C13 -H13B S7
8 N1 -C2 -C (3) C14 -C15 -H N2 -C3 -C (3) C16 -C15 -H N2 -C4 -C (3) C15 -C16 -H N2 -C4 -C (3) C17 -C16 -H C5 -C4 -C (3) C16 -C17 -H17A C4 -C5 -C (3) C16 -C17 -H17B Br3 -C6 -C (3) C18 -C17 -H17A Br3 -C6 -C (3) C18 -C17 -H17B C5 -C6 -C (3) H17A -C17 -H17B Br4 -C7 -C (3) C17 -C18 -H Br4 -C7 -C (3) C19 -C18 -H C6 -C7 -C (3) C14 -C19 -H C7 -C8 -C (3) C18 -C19 -H N3 -C9 -C (3) N4 -C20 -H20A N3 -C9 -C (3) N4 -C20 -H20B C4 -C9 -C (3) C21 -C20 -H20A Pd1 -C10 -N (3) C21 -C20 -H20B Pd1 -C10 -N (2) H20A -C20 -H20B N3 -C10 -N (3) C21 -C22 -H N4 -C11 -C (3) C23 -C22 -H N3 -C12 -C (3) C22 -C23 -H N1 -C13 -C (3) C24 -C23 -H C13 -C14 -C (3) C23 -C24 -H C13 -C14 -C (3) C25 -C24 -H C15 -C14 -C (4) C24 -C25 -H C14 -C15 -C (5) C26 -C25 -H C15 -C16 -C (5) C21 -C26 -H C16 -C17 -C (5) C25 -C26 -H C17 -C18 -C (5) Cl1 -C27 -Cl (4) C14 -C19 -C (4) Cl1 -C27 -H27A N4 -C20 -C (3) Cl1 -C27 -H27B C20 -C21 -C (4) Cl2 -C27 -H27A C20 -C21 -C (3) Cl2 -C27 -H27B C22 -C21 -C (4) H27A -C27 -H27B C21 -C22 -C (5) Cl3 -C28 -Cl3_a 110.7(4) Cl3 -C28 -H28A Cl3_a -C28 -H28A Cl3 -C28 -H28B Cl3_a -C28 -H28B H28A -C28 -H28B Figure F3 Ortep drawing with 50% ellipsoids for: Compound 11a S8
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