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1 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supplementary information Hybrids of acylated homoserine lactone and nitric oxide donors as inhibitors of quorum sensing and virulence factors in Pseudomonas aeruginosa Samuel K. Kutty a, Nicolas Barraud b, Kitty K. K. Ho a, George M. Iskander a, Renate Griffith c, Scott A. Rice d,e, Mark Willcox f, David StC Black a and Naresh Kumar a * Supporting Information 1) 1 H and 13 C NMR spectra of synthesised compounds tested for activity 2) X-ray crystal structure information for 7a and 22a
2 1) 1 H and 13 C NMR spectra of synthesised compounds 1 H NMR spectrum of Compound 7a in CDCl 3 N 2 13 C NMR spectrum of Compound 7a in CDCl 3
3 1 H NMR spectrum of Compound 7b in CDCl 3 N 2 13 C NMR spectrum of Compound 7b in CDCl 3
4 1 H NMR spectrum of Compound 7c in CDCl 3 N 2 13 C NMR spectrum of Compound 7c in CDCl 3
5 1 H NMR spectrum of Compound 7d in CDCl 3 N 2 13 C NMR spectrum of Compound 7d in CDCl 3
6 1 H NMR spectrum of Compound 7e in CDCl 3 N 2 13 C NMR spectrum of Compound 7e in CDCl 3
7 1 H NMR spectrum of Compound 10a in CDCl 3 N 2 13 C NMR spectrum of Compound 10a in CDCl 3
8 1 H NMR spectrum of Compound 10b in CDCl 3 N 2 13 C NMR spectrum of Compound 10b in CDCl 3
9 1 H NMR spectrum of Compound 13 in DMS-d6 H N N 2 13 C NMR spectrum of Compound 13 in DMS-d6
10 1 H NMR spectrum of Compound 21a in CDCl 3 N N N N Me 13 C NMR spectrum of Compound 21a in CDCl 3
11 1 H NMR spectrum of Compound 21b in CDCl 3 N N N N Me 13 C NMR spectrum of Compound 21b in CDCl 3
12 1 H NMR spectrum of Compound 22a in CDCl 3 N 2 N N N N N 2 2) X-ray crystal structure information Structure determination Reflexion data were measured with an Enraf-Nonius CAD-4 diffractometer in θ/2θ scan mode using nickel filtered copper radiation (γ Å). Reflexions with I>3σ(I) were considered observed. The structures were determined by direct phasing and Fourier methods. Hydrogen atoms were included in calculated position s and were assigned thermal parameters equal to those of the atom to which they were bonded. Positional and anisitropic thermal parameters for the nonhydrogen atoms were refined using full matrix least squares. Reflexion weights used were 1/σ2(Fo), with σ(fo) being derived from σ(io) = [σ2(io) + (0.04Io)2]1/2. The weighted residual is defined as Rw = (ΣwΔ2/ΣwFo2)1/2. Atomic scattering factors and anomalous dispersion parameters were from International Tables for X-ray crystallography1. Structure solutions were performed by SIR922 and refinements used RAELS3. RTEP-II4 running on a Macintosh was used for the structural diagrams.
13 Compound: 2-xo-2-(2-oxotetrahydrofuran-3-ylamino)ethyl nitrate (7a) Figure 1: RTEP diagram for 7a CCDC number: Table 1. Experimental details Crystal data inp21byn Chemical formula C 6 H 8 N 2 6 M r Crystal system, space group Temperature (K) 152 Monoclinic, P2 1 /n a, b, c (Å) (6), (2), (9) b ( ) (3) V (Å 3 ) (8) Z 4 Radiation type Mo Ka m (mm -1 ) 0.15 Crystal size (mm) Data collection Diffractometer Absorption correction Bruker kappa APEXII CCD Diffractometer Multi-scan SADABS (Bruker, 2001) T min, T max 0.934, No. of measured, independent and observed [I > 2s(I)] reflections R int Refinement 6746, 1812, 1552 R[F 2 > 2s(F 2 )], wr(f 2 ), S 0.032, 0.089, 1.04 No. of reflections 1812
14 No. of parameters 127 No. of restraints 0 H-atom treatment H-atom parameters constrained Dρ max, Dρ min (e Å -3 ) 0.27, Computer programs: APEX2 (Bruker, 2007), SHELXS-97 (Sheldrick, 2008), SHELXL-97 (Sheldrick, 2008), SHELXTL- Plus (Sheldrick, 2008). Table 2. Selected geometric parameters (Å, º) 1 C (15) C2 C (17) 1 C (17) C3 C (17) 2 C (16) C3 H C (15) C4 C (19) 4 N (15) C4 H4B C (15) C4 H4A N (16) C5 H5B N (15) C5 H5A N1 C (16) C6 C (17) N1 C (15) C7 H7B N1 H C7 H7A C2 1 C (10) C5 C4 H4B N2 4 C (9) C3 C4 H4A C6 N1 C (10) C5 C4 H4A C6 N1 H H4B C4 H4A C3 N1 H C5 C (10) 6 N (13) 1 C5 H5B N (11) C4 C5 H5B N (11) 1 C5 H5A C (12) C4 C5 H5A C2 C (11) H5B C5 H5A C2 C (10) 3 C6 N (11) N1 C3 C (10) 3 C6 C (11) N1 C3 C (10) N1 C6 C (10) C2 C3 C (10) 4 C7 C (10) N1 C3 H C7 H7B 109.7
15 C2 C3 H C6 C7 H7B C4 C3 H C7 H7A C3 C4 C (10) C6 C7 H7A C3 C4 H4B H7B C7 H7A C7 4 N (11) N1 C3 C4 C (11) C7 4 N (16) C2 C3 C4 C (12) C5 1 C (11) C2 1 C5 C (14) C5 1 C2 C (13) C3 C4 C (13) C6 N1 C3 C (13) C3 N1 C (19) C6 N1 C3 C (12) C3 N1 C6 C (10) 2 C2 C3 N (17) N2 4 C7 C (13) 1 C2 C3 N (10) 3 C6 C (16) 2 C2 C3 C (12) N1 C6 C (10) 1 C2 C3 C (13) Compound: 2 -(2,4-Dinitrophenyl)-1-(4-(4-oxo-4-(2-oxotetrahydrofuran-3-ylamino)butanoyl)piperazin-1-yl)diazen-1-ium- 1,2-diolate (22a). Figure 2: RTEP diagram for 22a. CCDC number Table 3. Experimental details sam12_p21byc Crystal data
16 Chemical formula C 18 H 17 N 7 10 CHCl 3 M r Crystal system, space group Monoclinic, P2 1 /c Temperature (K) 156 a, b, c (Å) (5), (1), (4) β ( ) (2) V (Å 3 ) (19) Z 4 Radiation type Mo Kα µ (mm -1 ) 0.43 Crystal size (mm) Data collection Diffractometer Absorption correction CCD area detector diffractometer Multi-scan SADABS2007/4 (Bruker,2007/4) was used for absorption correction. wr2(int) was before and after correction. The Ratio of minimum to maximum transmission is The λ/2 correction factor is T min, T max 0.667, No. of measured, independent and observed [I > 2σ(I)] reflections 17884, 4460, 3699
17 R int (sin / ) max (Å -1 ) Refinement R[F 2 > 2σ(F 2 )], wr(f 2 ), S 0.270, 0.675, 3.51 No. of reflections 4460 No. of parameters 380 No. of restraints 12 H-atom treatment H-atom parameters constrained max, min (e Å -3 ) 1.44, Computer programs: SAINT v7.46a (Bruker, 2008), SHELXL (Sheldrick, 2008), lex2 (Dolomanov et al., 2009). Table 4: Geometric parameters (Å, º) C1 C (19) C15 C19' 1.50 (3) C1 H C15' C16' 1.58 (4) C1CL H1CL C16' C17' 1.46 (5) C2 N (19) C16' H2XA C3 C (2) C16' H2XB C3 C (2) C17 C (5) C3 H C17 H3XA C4 C (2) C17 H3XB C4 N (17) C17' H1AA C (17) C17' H1AB C6 C (19) C19 C15' 1.56 (3) C6 C (2) C (17) C6 H C19 10' 1.35 (3) C7 C (2) Cl1 C1CL (18) C7 H7A Cl2 C1CL (19) C7 H7B Cl3 C1CL 1.78 (2) C8 H9A N (18) C8 H9B N (19) C8 N (19) N (17) C9 C (2) N (16) C9 H N3 N (17) C9 H N4 N (17) C9 N (18) N (16) C10 H10A N5 C (2)
18 C10 H10B N5 C (18) C11 C (3) N6 C (2) C (2) N7 C (4) C12 H N7 C15' 1.39 (3) C13 C (3) 5 N (16) C13 H H6A C14 C (2) 9 C19' (17) C14 N (3) 10 C (5) C (2) 10 C19' 1.55 (2) C15 C (3) 10' C17' 1.59 (4) Cl1 C1CL Cl (12) N6 C9 H Cl1 C1CL Cl (11) N6 C9 H Cl1 C1CL H1CL N6 C9 C (12) Cl2 C1CL Cl (11) H2 C9 H Cl2 C1CL H1CL C10 C9 H Cl3 C1CL H1CL C10 C9 H N3 5 C (10) N5 C10 C (11) N4 6 H6A N5 C10 H10A C19' 10 C (19) N5 C10 H10B N1 C (13) C9 C10 H10A N (14) C9 C10 H10B N1 C (14) H10A C10 H10B N (12) 7 C11 N (17) 3 N2 C (13) 7 C11 C (18) 4 N2 C (12) N6 C11 C (16) N4 N (11) C11 C12 H N4 N (13) C13 C12 C (16) 6 N4 N (12) C13 C12 H N3 N4 N (12) C12 C13 H N4 N5 C (12) C12 C13 C (17) C7 N5 N (11) C14 C13 H C7 N5 C (12) 8 C14 N (16) C9 N6 C (13) 8 C14 C (2) C11 N6 C (13) N7 C14 C (16) C11 N6 C (13) N7 C15' C (2) C14 N7 C15' 136 (2) N7 C15' C16' 113 (2) C14 N7 C (2) C19 C15' C16' 100 (2) C2 C1 H C19 C15' (18) C6 C1 H C19 10' (15) C6 C1 C (12) 10' C19 C15' (19) C1 C2 N (13) 9 C19' (13) C3 C2 N (13) 9 C19' C (15) C3 C2 C (12) C15 C19' (15) C2 C3 H C19 10' C17' 97 (2) C2 C3 C (12) C19' C15 N (19) C4 C3 H C16 C15 N7 122 (3) C3 C4 N (12) C16 C15 C19' 120 (2) C5 C4 N (13) 10' C17' H1AA C5 C4 C (12) 10' C17' H1AB C4 C (13) H1AA C17' H1AB 108.3
19 C4 C5 C (12) C16' C17' 10' 109 (3) C6 C (13) C16' C17' H1AA C1 C6 H C16' C17' H1AB C5 C6 C (12) C15' C16' H2XA C5 C6 H C15' C16' H2XB N5 C7 H7A C17' C16' C15' 100 (2) N5 C7 H7B C17' C16' H2XA N5 C7 C (14) C17' C16' H2XB H7A C7 H7B H2XA C16' H2XB C8 C7 H7A C17 H3XA C8 C7 H7B C17 H3XB N6 C8 C (11) H3XA C17 H3XB N6 C8 H9A C16 C (3) N6 C8 H9B C16 C17 H3XA C7 C8 H9A C16 C17 H3XB C7 C8 H9B C15 C16 C (2) H9A C8 H9B N3 N (19) C4 C3 C2 C1 3.5 (19) 5 N3 N4 N (10) C4 C5 5 N (11) 6 N4 N5 C (16) C5 5 N3 N (10) 6 N4 N5 C (12) C5 C4 N (15) 7 C11 C12 C13 13 (3) C5 C4 N (2) 8 C14 N7 C15' 10 (4) C5 C6 C1 C2 2.4 (17) 8 C14 N7 C15 7 (2) C6 C1 C2 N (11) 8 C14 C13 C12 26 (3) C6 C1 C2 C3 1.9 (18) 9 C19 C15' N7 46 (3) C6 C5 5 N3 4.9 (17) 9 C19 C15' C16' (17) C7 N5 C10 C (15) 9 C19 10' C17' 169 (3) C7 C8 N6 C (19) 10 C17 C16 C15 7 (4) C7 C8 N6 C (17) N2 C4 C (19) C8 N6 C (15) N2 C4 C5 C (11) C8 N6 C11 C12 5 (2) N3 N4 N5 C (13) C9 N6 C (2) N3 N4 N5 C (16) C9 N6 C11 C (16) N4 N5 C7 C (13) C10 N5 C7 C (17) N4 N5 C10 C (10) C10 C9 N6 C (16) N5 C7 C8 N (19) C10 C9 N6 C (15) N6 C9 C10 N (15) C13 C14 N7 C15' 174 (3) N6 C11 C12 C (19) C13 C14 N7 C (18) N7 C14 C13 C (2) C14 N7 C15' C19 33 (4) N7 C15' C16' C17' 151 (3) C14 N7 C15' C16' 80 (3) N7 C15 C19' 9 28 (4) C14 N7 C15 C19' 90 (2) N7 C15 C19' (2) C14 N7 C15 C (3) N7 C15 C16 C (3) C14 C13 C12 C (2) C1 C2 N (18) C15' C19 10' C17' 15 (4) C1 C2 N (13) C15' C16' C17' 10' 42 (5) C1 C6 C (11) C19 C15' C16' C17' 29 (3) C1 C6 C5 C4 4.9 (19) C19 10' C17' C16' 36 (5) C2 C3 C4 N (11) C19' 10 C17 C16 10 (3) C2 C3 C4 C5 1.0 (19) C19' C15 C16 C17 1 (5) C3 C2 N (13) 10' C19 C15' N7 129 (3)
20 C3 C2 N (19) 10' C19 C15' C16' 8 (3) C3 C4 N (18) C17 10 C19' (2) C3 C4 N (12) C17 10 C19' C15 10 (3) C3 C4 C (12) C16 C15 C19' (3) C3 C4 C5 C6 3 (2) C16 C15 C19' 10 6 (4) C4 C3 C2 N (11)
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