Dipole-Guided Electron Capture Causes Abnormal Dissociations of Phosphorylated Pentapeptides

Supplementary Material for Dipole-Guided Electron Capture Causes Abnormal Dissociations of Phosphorylated Pentapeptides Christopher L. Moss, a Thomas W. Chung, a Jean A. Wyer, b Steen Brøndsted Nielsen, b Preben Hvelplund, b František Tureček a * a Department of Chemistry, Bagley Hall, Box 35170, University of Washington, Seattle, WA 98195-1700, USA b Department of Physics and Astronomy, University of Aarhus, Aarhus, Denmark Manuscript submitted to the Journal of the American Society for Mass Spectrometry, October 2010. Figure S1. Relative intensities of z 1 -z 5 ions in the ETD spectra of pentapeptide ions. 1

Relative Intensity (%) Relative Intensity (%) 11 10 9 8 7 6 5 4 3 2 1 0 3 a 270 370 100 150 200 250 300 350 400 450 16 299 15 b 14 13 12 11 10 9 8 7 6 5 4 3 2 1 0 100 150 200 250 300 350 400 100 281 308 c -H 3 PO 4 z 3 (397) -H 3 PO 4 m/z z 4 (468) m/z Relative Intensity (%) 2 1 184 210 228 229 309 z 2 (326) 0 100 150 200 250 300 Figure S2. ETD-CID-MS 3 mass spectra of (a) z 4, (b) z 3, and (c) z 2 ions from (AAApSR + 2H) 2+ (4a 2+ ). m/z 2

12 10 a 457 -H 3 PO 4 Relative intensity (%) 8 6 4 2 0 y 2 y 3 y 4 246 317 388 psaaar 150 200 250 300 350 400 450 500 550 (555) m/z 12 b 457 -H 3 PO 4 Relative intensity (%) 10 8 6 4 2 0 y 2 y 3 246 413 AApSAR 150 200 250 300 350 400 450 500 550 (555) m/z 12 c 457 -H 3 PO 4 Relative intensity (%) 10 8 6 4 2 AAApSR (555) 0 150 200 250 300 350 400 450 500 550 m/z Figure S3. ETD-CID-MS 3 mass spectra of m/z 555 ions from (a) 1a 2+, (b) 3a 2+, and (c) 4a 2+ showing a predominant loss of phosphoric acid at m/z 457. 3

D 0.41 0.42 E 0.26 C B 0.16 0.07 A X 0.00 ev Figure S4. Electronic states in (AAApSR + 2H) + after vertical eletron attachement. Excitation energies are from TD-DFT calculations with B3LYP/6-311++G(2d,p). 4

Dipolar Field Effects μ = 10 D 0.208 +0.208 + 10 Å MO12,13, 3p x, 3p y 1.56 ev MO11,12, 3p x, 3p y 1.45 ev MO13, 3p z 1.41 ev 1.48 ev MO11, 3p z MO10, SOMO, 3s MO10, SOMO Figure S5. Frontier orbitals in CH 3 NH 3 radicals. Left panel: 3s and 3p orbitals without a dipolar field. Right panel: 3s and 3p orbitals in the presence of a superimposed 10-D dipole oriented along the C N bond. Excitation energies are from TD-DFT calculations with B3LYP/6-311++G(2df,2p) + additional very diffuse functions on N according to ref. [69]. 5

Table S1. Force-field Parameters for molecular dynamics calculations of phosphopeptide ions. Partial Charges: Bond Potentials V(bond) = K b (b b 0 ) 2 C β 0.08 Bond K b (kcal/(mol Å 2 ) b 0 (Å) H β 0.09 C β O γ 310 1.43 O γ 0.50 Angle Potentials V(angle) = K θ (θ θ 0 ) 2 P 1.9 Angle K θ (kcal/(mol rad 2 ) θ (degrees) O phosphony l 0.82 C α C β O γ 70 108.4 O hydroxyl 0.68 C β O γ P 20 120 H phosphate 0.34 H β C β O γ 60 109.5 Dihedral Potential V(dihedral) = K χ [1 + cos(nχ)-δ] K χ (kcal/mol) n δ (degrees) C α C β O γ P 0.6 1 180 C α C β O γ P 0.65 2 0 C α C β O γ P 0.05 3 0.0 C β O γ P O phosphonyl 0.1 3 0 C β O γ P O hydroxyl 0.95 2 0 C β O γ P O hydroxyl 0.5 3 0.0 6

Table S2. B3LYP/6-31+G(d,p) optimized structure of (psaaar + 2H) 2+ ion 1a 2+. Standard orientation: Center Atomic Atomic Coordinates (Angstroms) 1 7 0-1.837899-0.619415-1.901523 2 1 0-1.498169-0.289054-2.810631 3 1 0-2.151625-1.617321-1.925954 4 1 0-1.038487-0.557265-1.241714 5 6 0-2.943489 0.289378-1.438255 6 1 0-3.750484 0.214776-2.175833 7 6 0-3.486139-0.175512-0.078869 8 1 0-2.676842-0.327195 0.642991 9 1 0-4.173016 0.570643 0.324197 10 8 0-4.285342-1.362893-0.225823 11 6 0-2.336152 1.714745-1.523878 12 8 0-1.385940 1.881361-2.291608 13 15 0-3.677066-2.857063-0.092981 14 8 0-2.649940-3.129942-1.161519 15 8 0-3.120646-2.969968 1.382669 16 8 0-4.952288-3.768701-0.244636 17 1 0-2.149000-3.191376 1.425780 18 1 0-5.591784-3.779558 0.485761 19 7 0-2.877839 2.703128-0.788582 20 1 0-3.622336 2.520067-0.129624 21 6 0-2.275963 4.051826-0.762810 22 1 0-1.994825 4.294157-1.790643 23 6 0-3.278324 5.072020-0.229556 24 1 0-2.836529 6.071498-0.245509 25 1 0-4.173974 5.087456-0.856382 26 1 0-3.553296 4.847263 0.804775 27 6 0-1.022363 3.965161 0.138218 28 8 0-1.147160 3.859695 1.363543 29 7 0 0.168728 3.951015-0.506813 30 1 0 0.133170 3.860724-1.514323 31 6 0 1.502176 3.829998 0.116618 32 1 0 2.209192 3.901579-0.712201 33 6 0 1.807984 4.957659 1.115877 34 1 0 1.115838 4.957479 1.958934 35 1 0 2.827096 4.845295 1.497360 36 1 0 1.738341 5.922758 0.607480 37 6 0 1.741867 2.426444 0.714264 38 8 0 2.684976 1.706529 0.324611 39 7 0 0.898667 2.023882 1.677508 40 1 0 0.106120 2.635765 1.898317 41 6 0 0.977615 0.696934 2.265708 42 1 0 1.956650 0.587690 2.748498 43 6 0-0.130555 0.516602 3.312926 44 1 0-0.020816 1.264723 4.102430 45 1 0-1.118903 0.631182 2.859021 46 1 0-0.074150-0.473158 3.772861 47 6 0 0.869103-0.369424 1.160801 48 8 0 0.068668-0.273055 0.221016 49 6 0 0.274174-3.150711 0.290417 7

50 8 0-0.462349-3.199994 1.267294 51 8 0-0.033679-3.578024-0.922780 52 1 0-1.003826-3.780918-0.984881 53 7 0 1.707576-1.428110 1.284502 54 1 0 2.187944-1.551598 2.166792 55 6 0 1.680574-2.540727 0.344110 56 1 0 1.877682-2.144960-0.657656 57 6 0 2.745129-3.594524 0.703925 58 1 0 2.464036-4.076233 1.648089 59 1 0 2.709669-4.374181-0.064203 60 6 0 4.191274-3.074043 0.839661 61 1 0 4.296611-2.387046 1.688603 62 1 0 4.808597-3.940322 1.098180 63 6 0 4.834688-2.435674-0.400865 64 1 0 5.922467-2.483341-0.273073 65 1 0 4.570678-3.010827-1.298392 66 7 0 4.453461-1.022676-0.590654 67 1 0 3.765487-0.606203 0.029214 68 6 0 5.068974-0.188080-1.443320 69 7 0 4.719060 1.099707-1.485188 70 1 0 5.189116 1.733985-2.113523 71 1 0 3.991229 1.474724-0.862089 72 7 0 6.029074-0.650249-2.262079 73 1 0 6.313747-1.616799-2.259816 74 1 0 6.520750-0.031928-2.890285 Rotational constants (GHZ): 0.1003021 0.0878009 0.0561473 E[B3LYP/6-31+G(d,p)] = -2239.70739332 a.u. E[B3LYP/6-311++G(2d,p)] = -2240.2389716 a.u. E[MP2/6-311++G(2d,p)] = -2235.0545331067 a.u. ZPVE = 1621.508 kj mol -1. Table S3. B3LYP/6-31+G(d,p) optimized structure of (psaaar + 2H) 2+ ion 1b 2+. Standard orientation: Center Atomic Atomic Coordinates (Angstroms) 1 7 0 1.426551 1.987955-1.379611 2 1 0 0.575588 1.405120-1.466035 3 1 0 1.181654 2.939263-1.668583 4 1 0 1.681596 2.002860-0.355597 5 6 0 2.569121 1.372048-2.147657 6 1 0 2.487149 1.724045-3.181130 7 6 0 3.936810 1.832435-1.610321 8 1 0 4.684683 1.705128-2.395551 9 1 0 3.905854 2.895529-1.348414 10 8 0 4.434272 1.052308-0.504194 11 6 0 2.236589-0.147013-2.186725 12 8 0 1.093126-0.462063-2.503765 13 15 0 3.880723 1.167525 1.029597 14 8 0 2.507357 1.762585 1.054370 15 8 0 4.075214-0.299641 1.570132 16 8 0 4.917842 2.047018 1.842980 17 1 0 3.432196-0.981823 1.213022 8

18 1 0 5.762680 1.625825 2.069476 19 7 0 3.186645-1.046625-1.844843 20 1 0 4.053098-0.715234-1.436553 21 6 0 2.811858-2.444272-1.628414 22 1 0 2.249712-2.776831-2.505396 23 6 0 4.062993-3.312398-1.449681 24 1 0 4.691280-3.245210-2.341598 25 1 0 4.645830-2.997902-0.578559 26 1 0 3.783764-4.359675-1.309674 27 6 0 1.905156-2.531220-0.379702 28 8 0 2.233812-1.986082 0.695284 29 7 0 0.770952-3.237029-0.511945 30 1 0 0.525547-3.525456-1.450000 31 6 0-0.216073-3.557037 0.544578 32 1 0-0.944868-4.202727 0.051787 33 6 0 0.395284-4.324285 1.725925 34 1 0 1.153011-3.743662 2.253490 35 1 0-0.393168-4.592555 2.434949 36 1 0 0.853852-5.248130 1.363635 37 6 0-1.042028-2.319086 0.971982 38 8 0-2.256658-2.254151 0.694551 39 7 0-0.407410-1.372891 1.681187 40 1 0 0.608625-1.432947 1.716528 41 6 0-1.042771-0.125591 2.082542 42 1 0-2.019867-0.374338 2.511953 43 6 0-0.181409 0.595147 3.132515 44 1 0 0.780141 0.902894 2.711144 45 1 0-0.687901 1.490164 3.503364 46 1 0-0.009329-0.065763 3.986027 47 6 0-1.277131 0.751494 0.832808 48 8 0-0.731401 0.497279-0.242324 49 6 0-1.691426 3.897771-0.195468 50 8 0-0.648403 3.996928-0.816565 51 8 0-2.195400 4.869112 0.571938 52 1 0-1.606124 5.645305 0.544743 53 7 0-2.137346 1.796932 0.975688 54 1 0-2.536585 2.002244 1.883309 55 6 0-2.536996 2.615154-0.173862 56 1 0-2.203424 2.056706-1.049325 57 6 0-4.058746 2.845578-0.223006 58 1 0-4.359248 3.519755 0.585527 59 1 0-4.286276 3.374086-1.156581 60 6 0-4.890203 1.550837-0.117210 61 1 0-4.715069 1.087377 0.859049 62 1 0-5.948250 1.831792-0.129207 63 6 0-4.610106 0.484882-1.212515 64 1 0-5.395650 0.472979-1.973387 65 1 0-3.689949 0.705879-1.758753 66 7 0-4.431065-0.869458-0.675657 67 1 0-3.514419-1.105955-0.292306 68 6 0-5.358615-1.818665-0.528459 69 7 0-4.991612-2.993386 0.004545 70 1 0-4.033455-3.112247 0.327410 71 1 0-5.668846-3.712403 0.208308 72 7 0-6.634222-1.628372-0.905548 73 1 0-7.303682-2.383036-0.876908 74 1 0-6.940378-0.764818-1.324062 9

Rotational constants (GHZ): 0.1282831 0.0754003 0.0585558 E[B3LYP/6-31+G(d,p)] = -2239.70481491 a.u. E[B3LYP/6-311++G(2d,p)] = -2240.23556466 a.u. E[MP2/6-311++G(2d,p)] = -2235.0524820652 a.u. ZPVE = 1621.9377 kj mol -1. Table S4. B3LYP/6-31+G(d,p) optimized structure of (psaaar + 2H) 2+ ion 1c 2+. Standard orientation: Center Atomic Atomic Coordinates (Angstroms) 1 7 0 1.709635 2.031692-1.337710 2 1 0 1.555999 3.001614-1.624144 3 1 0 1.990644 2.015257-0.320540 4 1 0 0.799722 1.541539-1.395940 5 6 0 2.763606 1.310941-2.141944 6 1 0 2.700361 1.693400-3.165796 7 6 0 4.184172 1.610428-1.627385 8 1 0 4.896759 1.418076-2.431996 9 1 0 4.273636 2.665570-1.347475 10 8 0 4.618672 0.761244-0.546016 11 6 0 2.271345-0.163612-2.212091 12 8 0 1.104709-0.351084-2.542525 13 15 0 4.114029 0.913638 1.002429 14 8 0 2.824881 1.669893 1.065821 15 8 0 4.147579-0.575950 1.514878 16 8 0 5.267697 1.646312 1.805400 17 1 0 3.438597-1.186208 1.151268 18 1 0 6.055467 1.117784 2.011132 19 7 0 3.124784-1.161687-1.886320 20 1 0 4.022878-0.926030-1.479987 21 6 0 2.621446-2.521884-1.702609 22 1 0 2.002238-2.766232-2.570001 23 6 0 3.787820-3.512222-1.596092 24 1 0 4.391026-3.474170-2.506817 25 1 0 4.425183-3.284249-0.736348 26 1 0 3.413554-4.532273-1.478451 27 6 0 1.752619-2.571876-0.425180 28 8 0 2.164528-2.099661 0.654852 29 7 0 0.558158-3.174746-0.542218 30 1 0 0.259645-3.403332-1.481202 31 6 0-0.418959-3.455168 0.535140 32 1 0-1.211581-4.023631 0.045500 33 6 0 0.166276-4.307539 1.669782 34 1 0 0.536580-5.253086 1.264665 35 1 0 0.985489-3.807689 2.188163 36 1 0-0.617794-4.533963 2.398002 37 6 0-1.128525-2.169390 1.023748 38 8 0-2.329330-1.976513 0.766793 39 7 0-0.399887-1.307063 1.755666 40 1 0 0.608413-1.444708 1.761235 41 6 0-0.922422-0.003737 2.141019 42 1 0-1.896879-0.160820 2.615803 10

43 6 0 0.034513 0.685898 3.125739 44 1 0 1.000684 0.895509 2.657315 45 1 0-0.385400 1.634601 3.471100 46 1 0 0.186296 0.049479 4.001687 47 6 0-1.117382 0.847505 0.870277 48 8 0-0.432644 0.662283-0.135222 49 6 0-1.479717 3.905684-0.150877 50 8 0-0.420315 4.005688-0.741037 51 8 0-1.965450 4.841066 0.675136 52 1 0-1.347548 5.593894 0.713821 53 7 0-2.089215 1.799004 0.918730 54 1 0-2.569058 1.979848 1.791744 55 6 0-2.381800 2.664066-0.228783 56 1 0-2.045105 2.120071-1.114447 57 6 0-3.884713 2.978531-0.329056 58 1 0-4.275306 3.245214 0.660569 59 1 0-4.008541 3.875291-0.944173 60 6 0-4.735263 1.863580-0.968963 61 1 0-5.765296 2.239174-1.024867 62 1 0-4.400555 1.698699-2.000931 63 6 0-4.739124 0.521038-0.225176 64 1 0-3.758332 0.043187-0.278307 65 1 0-4.993754 0.661398 0.832683 66 7 0-5.743987-0.369394-0.838543 67 1 0-6.375718 0.042803-1.513062 68 6 0-5.980997-1.639961-0.486162 69 7 0-7.124634-2.228330-0.885978 70 1 0-7.901221-1.690262-1.241443 71 1 0-7.246841-3.228810-0.829852 72 7 0-5.112077-2.325987 0.258137 73 1 0-5.381973-3.225402 0.629491 74 1 0-4.132129-2.060448 0.389847 Rotational constants (GHZ): 0.1302443 0.0698746 0.0556840 E[B3LYP/6-31+G(d,p)] = -2239.70404274 a.u. E[B3LYP/6-311++G(2d,p)] = -2240.23499276 a.u. E[MP2/6-311++G(2d,p)] = -2235.0506639051 a.u. ZPVE = 1621.1866 kj mol -1. Table S5. B3LYP/6-31+G(d,p) optimized structure of (psaaar + 2H) 2+ ion 1d 2+. Standard orientation: Center Atomic Atomic Coordinates (Angstroms) 1 7 0 1.619757 2.044744-1.337511 2 1 0 0.727603 1.521948-1.380233 3 1 0 1.425771 3.004881-1.632290 4 1 0 1.912919 2.046802-0.323963 5 6 0 2.689029 1.355424-2.148508 6 1 0 2.601187 1.728649-3.173971 7 6 0 4.104361 1.706434-1.652232 8 1 0 4.813194 1.538344-2.465519 9 1 0 4.159199 2.764655-1.375032 10 8 0 4.582500 0.875518-0.575549 11

11 6 0 2.247511-0.135103-2.203395 12 8 0 1.080741-0.364597-2.507434 13 15 0 4.087342 1.010010 0.977782 14 8 0 2.777738 1.728793 1.053644 15 8 0 4.169269-0.478248 1.488315 16 8 0 5.227025 1.774889 1.770901 17 1 0 3.474203-1.110629 1.133639 18 1 0 6.029428 1.267441 1.972970 19 7 0 3.141550-1.102212-1.895132 20 1 0 4.038400-0.836182-1.505059 21 6 0 2.686970-2.478510-1.701761 22 1 0 2.072202-2.748750-2.564665 23 6 0 3.887067-3.427356-1.596685 24 1 0 4.519645-3.174993-0.740227 25 1 0 3.548221-4.459138-1.474156 26 1 0 4.484931-3.372169-2.510075 27 6 0 1.825837-2.550180-0.420281 28 8 0 2.229578-2.066458 0.657642 29 7 0 0.647262-3.183710-0.532370 30 1 0 0.351033-3.422567-1.469446 31 6 0-0.320022-3.477639 0.549244 32 1 0-1.107520-4.056805 0.063932 33 6 0 0.282888-4.322052 1.680179 34 1 0 1.100588-3.813575 2.192659 35 1 0-0.493155-4.557635 2.414013 36 1 0 0.661087-5.263379 1.272538 37 6 0-1.046087-2.200469 1.036541 38 8 0-2.238423-2.007677 0.744363 39 7 0-0.345894-1.349307 1.808612 40 1 0 0.663364-1.473891 1.832292 41 6 0-0.894952-0.061546 2.210958 42 1 0-1.859517-0.245018 2.696887 43 6 0 0.057509 0.643440 3.188645 44 1 0 1.009970 0.884570 2.707535 45 1 0-0.383160 1.576482 3.550204 46 1 0 0.240352 0.002814 4.055632 47 6 0-1.129451 0.792167 0.949620 48 8 0-0.454968 0.628479-0.066923 49 6 0-1.612208 3.802338-0.176373 50 8 0-0.599067 3.916591-0.841085 51 8 0-2.071268 4.751386 0.648690 52 1 0-1.474974 5.521740 0.621022 53 7 0-2.119944 1.723425 1.015445 54 1 0-2.608117 1.880227 1.888023 55 6 0-2.475681 2.529779-0.153396 56 1 0-2.147542 1.955163-1.021998 57 6 0-3.986792 2.808115-0.222297 58 1 0-4.273355 3.493368 0.581989 59 1 0-4.178656 3.345202-1.159059 60 6 0-4.888758 1.559671-0.147792 61 1 0-4.856604 1.123548 0.856934 62 1 0-5.920023 1.895693-0.304080 63 6 0-4.564283 0.464587-1.180054 64 1 0-4.420247 0.897110-2.174439 65 1 0-3.641212-0.067292-0.934806 66 7 0-5.658827-0.513460-1.328187 67 1 0-6.350657-0.304519-2.035794 12

68 6 0-5.923356-1.566000-0.540811 69 7 0-7.138241-2.143043-0.617553 70 1 0-7.908932-1.696163-1.092152 71 1 0-7.306545-3.062549-0.236280 72 7 0-5.024086-2.053060 0.314897 73 1 0-5.306348-2.765363 0.972774 74 1 0-4.020405-1.859808 0.285922 Rotational constants (GHZ): 0.1323212 0.0698311 0.0564102 E[B3LYP/6-31+G(d,p)] = -2239.70318444 a.u. E[B3LYP/6-311++G(2d,p)] = -2240.23412702 a.u. E[MP2/6-311++G(2d,p)] = -2235.0502969019 a.u. ZPVE = 1621.8495 kj mol -1. Table S6. B3LYP/6-31+G(d,p) optimized structure of (psaaar + 2H) 2+ ion 1e 2+. Standard orientation: Center Atomic Atomic Coordinates (Angstroms) 1 7 0-2.070237-2.193442-1.391173 2 1 0-2.377288-2.245170-0.376544 3 1 0-1.147027-1.717880-1.398676 4 1 0-1.957454-3.139127-1.760272 5 6 0-3.108125-1.405981-2.152781 6 1 0-3.014296-1.688026-3.206961 7 6 0-4.540953-1.757480-1.704598 8 1 0-5.231279-1.521265-2.516967 9 1 0-4.624854-2.830157-1.499041 10 8 0-5.017313-0.987989-0.584585 11 6 0-2.636000 0.069177-2.060325 12 8 0-1.435969 0.290033-2.207037 13 15 0-4.519792-1.226531 0.957068 14 8 0-3.225639-1.979107 0.970856 15 8 0-4.553930 0.228970 1.556407 16 8 0-5.670078-2.011910 1.708981 17 1 0-3.825947 0.841172 1.237117 18 1 0-6.450045-1.498523 1.974427 19 7 0-3.541324 1.041874-1.816189 20 1 0-4.467693 0.781726-1.497197 21 6 0-3.068473 2.394507-1.517320 22 1 0-2.477097 2.739981-2.370737 23 6 0-4.256862 3.336553-1.292358 24 1 0-4.864395 3.016093-0.440506 25 1 0-3.905335 4.352165-1.094729 26 1 0-4.884564 3.364497-2.186989 27 6 0-2.163596 2.336120-0.267035 28 8 0-2.517186 1.712913 0.756240 29 7 0-0.998194 2.995234-0.343159 30 1 0-0.743450 3.353701-1.254008 31 6 0 0.017141 3.157760 0.719800 32 1 0 0.755821 3.837728 0.291931 33 6 0-0.545709 3.795062 2.000160 34 1 0-0.985350 4.768199 1.765439 35 1 0-1.306362 3.171299 2.470808 13

36 1 0 0.267420 3.953366 2.714267 37 6 0 0.822704 1.866718 1.010123 38 8 0 2.061109 1.872554 0.898902 39 7 0 0.142366 0.788809 1.436502 40 1 0-0.872775 0.846439 1.465393 41 6 0 0.797796-0.448911 1.856725 42 1 0 1.690633-0.160642 2.420909 43 6 0-0.143988-1.262444 2.754613 44 1 0-1.057404-1.543201 2.222692 45 1 0 0.350202-2.177624 3.091990 46 1 0-0.412057-0.679172 3.640022 47 6 0 1.235046-1.290724 0.638978 48 8 0 0.463826-1.561445-0.289386 49 6 0 4.187467-3.512717 0.256266 50 8 0 4.770639-4.345729-0.392045 51 8 0 4.467377-3.235237 1.552992 52 1 0 5.169820-3.841848 1.850055 53 7 0 2.512577-1.734155 0.678734 54 1 0 3.058254-1.573734 1.515357 55 6 0 3.064007-2.650463-0.320586 56 1 0 2.267187-3.349177-0.600949 57 6 0 3.528402-1.963966-1.629725 58 1 0 3.804410-2.770584-2.314592 59 1 0 2.660362-1.457045-2.064089 60 6 0 4.718786-0.991397-1.526893 61 1 0 5.539566-1.442621-0.955676 62 1 0 5.100016-0.839438-2.545298 63 6 0 4.361448 0.375502-0.932694 64 1 0 3.514323 0.813513-1.474200 65 1 0 4.070949 0.290542 0.114771 66 7 0 5.520510 1.281801-1.011717 67 1 0 6.188020 1.113179-1.753889 68 6 0 5.691545 2.388203-0.278981 69 7 0 6.860189 3.054494-0.357394 70 1 0 7.672220 2.645976-0.796042 71 1 0 6.966217 3.976725 0.038332 72 7 0 4.730863 2.837285 0.532134 73 1 0 4.947695 3.555858 1.207562 74 1 0 3.774665 2.470207 0.545286 Rotational constants (GHZ): 0.1385603 0.0597059 0.0500096 E[B3LYP/6-31+G(d,p)] = -2239.70163538 a.u. E[B3LYP/6-311++G(2d,p)] = -2240.23291914 a.u. E[MP2/6-311++G(2d,p)] = -2235.0461738041 a.u. ZPVE = 1620.4603 kj mol -1. Table S7. B3LYP/6-31+G(d,p) optimized structure of (ApSAAR + 2H) 2+ ion 2a 2+. Standard orientation: Center Atomic Atomic Coordinates (Angstroms) 1 7 0 8.304860 1.025281 0.883476 2 1 0 9.243767 1.199034 0.517533 3 1 0 7.999227 0.023781 0.683319 14

4 1 0 8.310197 1.151643 1.902978 5 6 0 7.275857 1.963125 0.287081 6 1 0 7.233655 1.724779-0.779124 7 6 0 7.659265 3.420576 0.523091 8 1 0 8.629048 3.650157 0.070827 9 1 0 6.916183 4.076057 0.061011 10 1 0 7.693352 3.646536 1.592581 11 6 0 5.980071 1.555120 1.017800 12 8 0 5.976166 1.526906 2.245222 13 7 0 4.941956 1.170047 0.240939 14 1 0 5.035041 1.171051-0.768045 15 6 0 3.783601 0.459669 0.782225 16 1 0 3.314165 1.069320 1.562390 17 6 0 4.191165-0.882142 1.441877 18 1 0 4.987638-0.704825 2.166372 19 1 0 3.330153-1.314454 1.955506 20 8 0 4.593793-1.881822 0.485493 21 6 0 2.815530 0.216859-0.387883 22 8 0 3.258303 0.002232-1.531464 23 15 0 5.985853-1.889605-0.329711 24 8 0 7.143392-1.309714 0.430051 25 8 0 6.166852-3.414328-0.738077 26 8 0 5.685351-1.173985-1.710261 27 1 0 6.672811-3.948510-0.106318 28 1 0 4.750531-0.849923-1.805908 29 7 0 1.509727 0.216450-0.100804 30 1 0 1.166622 0.381878 0.842644 31 6 0 0.477914-0.121793-1.080564 32 1 0 0.850594-0.957784-1.683769 33 6 0 0.147793 1.065001-2.006925 34 1 0-0.577975 0.769726-2.770560 35 1 0-0.268380 1.901375-1.438763 36 1 0 1.056355 1.389507-2.518320 37 6 0-0.747883-0.569326-0.264579 38 8 0-0.834227-0.335828 0.937563 39 7 0-1.740844-1.197852-0.964789 40 1 0-1.543743-1.493505-1.913123 41 6 0-2.873652-1.830294-0.284148 42 1 0-2.545933-2.102275 0.724343 43 6 0-3.317730-3.090187-1.041310 44 1 0-4.166255-3.550375-0.532059 45 1 0-3.619323-2.855398-2.068452 46 1 0-2.501525-3.816789-1.072694 47 6 0-4.066745-0.887896-0.058043 48 8 0-4.986351-1.257564 0.696826 49 6 0-4.167667 2.664836-0.398369 50 8 0-3.037513 2.749696-0.831627 51 8 0-4.852947 3.680825 0.141809 52 1 0-4.303225 4.484718 0.114918 53 7 0-4.073180 0.286028-0.712277 54 1 0-3.225326 0.549698-1.205696 55 6 0-5.000944 1.380204-0.437193 56 1 0-5.431642 1.229831 0.556801 57 6 0-6.123515 1.535811-1.499066 58 1 0-6.668911 2.458066-1.270676 59 1 0-5.638624 1.691677-2.469728 60 6 0-7.126339 0.376759-1.652852 15

61 1 0-7.685071 0.564114-2.575574 62 1 0-6.605945-0.575743-1.809263 63 6 0-8.175404 0.210691-0.540824 64 1 0-8.591999 1.192013-0.275543 65 1 0-8.993212-0.415229-0.919288 66 7 0-7.593811-0.425306 0.647682 67 1 0-6.598844-0.706466 0.608993 68 6 0-8.264575-0.819840 1.724342 69 7 0-9.566087-0.527920 1.886885 70 1 0-10.092942-0.883874 2.670349 71 1 0-10.065810 0.029850 1.212177 72 7 0-7.619403-1.529053 2.668475 73 1 0-6.647342-1.776247 2.535580 74 1 0-8.050631-1.757436 3.550917 Rotational constants (GHZ): 0.2147570 0.0287318 0.0273621 E[B3LYP/6-31+G(d,p)] = -2239.7189239 a.u. E[B3LYP/6-311++G(2d,p)] = -2240.25120768 a.u. E[MP2/6-311++G(2d,p)] = -2235.0566293822 a.u. ZPVE = 1617.2529 kj mol -1. Table S8. B3LYP/6-31+G(d,p) optimized structure of (ApSAAR + 2H) 2+ ion 2b 2+. Standard orientation: Center Atomic Atomic Coordinates (Angstroms) 1 7 0 8.269182 1.190530 0.859523 2 1 0 9.201148 1.400005 0.494646 3 1 0 8.001300 0.180265 0.662387 4 1 0 8.267124 1.321315 1.878448 5 6 0 7.202086 2.078474 0.254558 6 1 0 7.171877 1.829244-0.809523 7 6 0 7.521964 3.553247 0.477133 8 1 0 6.752019 4.171669 0.007965 9 1 0 7.544465 3.790642 1.544415 10 1 0 8.481738 3.820079 0.023979 11 6 0 5.923565 1.623226 0.987629 12 8 0 5.915531 1.618293 2.214875 13 7 0 4.904348 1.178434 0.216631 14 1 0 4.992538 1.171056-0.792722 15 6 0 3.772038 0.439708 0.775393 16 1 0 3.282685 1.051233 1.541763 17 6 0 4.219409-0.874631 1.466523 18 1 0 5.020717-0.659245 2.174623 19 1 0 3.374904-1.310959 2.003622 20 8 0 4.632375-1.889320 0.531139 21 6 0 2.815652 0.143420-0.390426 22 8 0 3.271446-0.096899-1.524633 23 15 0 6.030647-1.895795-0.274961 24 8 0 7.123863-1.132721 0.399236 25 8 0 6.424340-3.425949-0.416151 26 8 0 5.639460-1.408016-1.740809 27 1 0 5.933432-3.931162-1.081753 28 1 0 4.749986-0.965163-1.787112 16

29 7 0 1.508559 0.131660-0.111471 30 1 0 1.158928 0.323361 0.824822 31 6 0 0.482055-0.241188-1.084126 32 1 0 0.850902-1.106021-1.648036 33 6 0 0.167182 0.906493-2.063506 34 1 0 1.081520 1.202097-2.581930 35 1 0-0.555290 0.583364-2.818915 36 1 0-0.246801 1.769612-1.535109 37 6 0-0.752474-0.644232-0.256974 38 8 0-0.836496-0.371847 0.937067 39 7 0-1.754404-1.279476-0.937823 40 1 0-1.563377-1.605448-1.877397 41 6 0-2.896348-1.873623-0.237700 42 1 0-2.571265-2.121985 0.777678 43 6 0-3.362299-3.147043-0.957917 44 1 0-4.217610-3.577999-0.434652 45 1 0-3.661579-2.936919-1.991051 46 1 0-2.558541-3.887988-0.969004 47 6 0-4.073615-0.905850-0.036701 48 8 0-4.995932-1.238261 0.731840 49 6 0-4.120458 2.635969-0.486289 50 8 0-2.990542 2.689349-0.925362 51 8 0-4.787992 3.679030 0.023311 52 1 0-4.226098 4.473094-0.030377 53 7 0-4.064148 0.247484-0.726637 54 1 0-3.214043 0.482861-1.230393 55 6 0-4.973700 1.363977-0.482138 56 1 0-5.402578 1.250938 0.517517 57 6 0-6.098319 1.504275-1.543990 58 1 0-6.630578 2.439788-1.340000 59 1 0-5.615189 1.626221-2.520396 60 6 0-7.116355 0.354407-1.661676 61 1 0-7.673662 0.520610-2.589291 62 1 0-6.608292-0.608999-1.789448 63 6 0-8.166708 0.235478-0.544856 64 1 0-8.573883 1.229039-0.312662 65 1 0-8.990526-0.394734-0.902718 66 7 0-7.591315-0.365607 0.664692 67 1 0-6.602081-0.666427 0.632463 68 6 0-8.264108-0.706555 1.758452 69 7 0-9.560444-0.388776 1.913033 70 1 0-10.088438-0.700650 2.714323 71 1 0-10.055609 0.144655 1.215669 72 7 0-7.625713-1.385794 2.728746 73 1 0-6.657796-1.652302 2.603470 74 1 0-8.060032-1.580000 3.617828 Rotational constants (GHZ): 0.2118610 0.0287995 0.0273999 E[B3LYP/6-31+G(d,p)] = -2239.7175198 a.u. E[B3LYP/6-311++G(2d,p)] = -2240.24977302 a.u. E[MP2/6-311++G(2d,p)] = -2235.0548682812 a.u. ZPVE = 1617.1123 kj mol -1. Table S9. B3LYP/6-31+G(d,p) optimized structure of (ApSAAR + 2H) 2+ ion 2c 2+. 17

Standard orientation: Center Atomic Atomic Coordinates (Angstroms) 1 7 0-6.797820 2.343972 0.777685 2 1 0-6.103003 1.891870 1.439125 3 1 0-7.664968 1.794019 0.823173 4 1 0-6.993476 3.308257 1.055492 5 6 0-6.253034 2.248865-0.635019 6 1 0-5.288175 2.762264-0.621765 7 6 0-7.217000 2.876971-1.635267 8 1 0-8.173802 2.347275-1.639883 9 1 0-7.386773 3.934707-1.410872 10 1 0-6.792707 2.816088-2.641126 11 6 0-6.091553 0.726078-0.818661 12 8 0-7.065180 0.006650-0.600911 13 7 0-4.848322 0.284111-1.089354 14 1 0-4.110240 0.922334-1.369191 15 6 0-4.459995-1.121810-1.011645 16 1 0-5.021443-1.704017-1.757012 17 6 0-4.790662-1.735688 0.362080 18 1 0-5.810769-1.474439 0.644130 19 1 0-4.724798-2.825032 0.310681 20 8 0-3.871683-1.361033 1.415378 21 6 0-2.967763-1.159605-1.416742 22 8 0-2.502799-0.280178-2.140819 23 15 0-3.717951 0.115970 2.049359 24 8 0-4.993682 0.895663 2.111318 25 8 0-3.033208-0.193985 3.456073 26 8 0-2.588778 0.860538 1.235141 27 1 0-3.627994-0.549001 4.134846 28 1 0-1.778631 0.337368 0.988229 29 7 0-2.213757-2.184839-0.954325 30 1 0-2.555046-2.749929-0.189444 31 6 0-0.785286-2.233260-1.235481 32 1 0-0.656495-2.296171-2.321995 33 6 0-0.172879-3.472740-0.565687 34 1 0-0.300780-3.431149 0.520488 35 1 0-0.652176-4.377671-0.949504 36 1 0 0.897443-3.542952-0.770823 37 6 0-0.086825-0.951728-0.730660 38 8 0-0.401180-0.394620 0.324915 39 7 0 0.969655-0.533878-1.484096 40 1 0 1.032715-0.903879-2.425396 41 6 0 1.689914 0.712050-1.211545 42 1 0 1.114959 1.248787-0.450708 43 6 0 1.796561 1.571800-2.480030 44 1 0 2.334829 2.495159-2.259443 45 1 0 2.333424 1.044050-3.276732 46 1 0 0.797120 1.824949-2.841909 47 6 0 3.076896 0.493589-0.583020 48 8 0 3.732475 1.484356-0.208248 49 6 0 4.303876-2.452510 1.034730 50 8 0 3.325252-3.117881 0.765348 51 8 0 5.182775-2.747109 1.999659 52 1 0 4.916362-3.579261 2.431187 18

53 7 0 3.523708-0.770248-0.485194 54 1 0 2.865974-1.514529-0.697702 55 6 0 4.701560-1.183763 0.273462 56 1 0 4.937708-0.407034 1.006148 57 6 0 5.940012-1.497277-0.610314 58 1 0 6.707818-1.931196 0.039742 59 1 0 5.648433-2.283475-1.316305 60 6 0 6.554487-0.339823-1.419364 61 1 0 7.255944-0.790630-2.128958 62 1 0 5.795491 0.161328-2.032096 63 6 0 7.354640 0.711162-0.633018 64 1 0 8.003550 0.210250 0.098218 65 1 0 7.993087 1.264125-1.333300 66 7 0 6.463443 1.655611 0.052556 67 1 0 5.443991 1.538585-0.074444 68 6 0 6.846591 2.745476 0.708593 69 7 0 8.144681 3.011221 0.930184 70 1 0 8.440302 3.871814 1.366306 71 1 0 8.867841 2.375204 0.632362 72 7 0 5.907768 3.599202 1.157003 73 1 0 4.930627 3.414901 0.971626 74 1 0 6.138263 4.375475 1.757952 Rotational constants (GHZ): 0.1763658 0.0376544 0.0357214 E[B3LYP/6-31+G(d,p)] = -2239.71574418 a.u. E[B3LYP/6-311++G(2d,p)] = -2240.24756939 a.u. E[MP2/6-311++G(2d,p)] = -2235.0562562586 a.u. ZPVE = 1617.3351 kj mol -1. Table S10. B3LYP/6-31+G(d,p) optimized structure of (ApSAAR + 2H) 2+ ion 2d 2+. Standard orientation: Center Atomic Atomic Coordinates (Angstroms) 1 7 0 8.234482 1.328690-0.184102 2 1 0 7.946888 0.372315 0.177214 3 1 0 8.264809 1.970909 0.617262 4 1 0 9.157659 1.292228-0.622351 5 6 0 7.160981 1.799064-1.142993 6 1 0 7.095986 1.032751-1.920033 7 6 0 7.506317 3.165026-1.728159 8 1 0 6.731378 3.468247-2.437320 9 1 0 7.562616 3.923362-0.942188 10 1 0 8.456030 3.131841-2.270988 11 6 0 5.899237 1.826828-0.256532 12 8 0 5.931558 2.453951 0.797814 13 7 0 4.845408 1.085364-0.670260 14 1 0 4.899656 0.554678-1.531806 15 6 0 3.718110 0.780317 0.210281 16 1 0 3.263918 1.715416 0.557085 17 6 0 4.160782-0.002401 1.473730 18 1 0 4.987792 0.519276 1.957372 19 1 0 3.324854-0.071725 2.172683 20 8 0 4.521938-1.366823 1.185423 19

21 6 0 2.720802-0.048226-0.614453 22 8 0 3.134051-0.840077-1.481733 23 15 0 5.896047-1.835698 0.479924 24 8 0 7.016973-0.860066 0.628481 25 8 0 6.267534-3.220481 1.158158 26 8 0 5.465357-2.188076-1.014323 27 1 0 5.757394-3.990049 0.863611 28 1 0 4.591452-1.797682-1.278090 29 7 0 1.423350 0.105770-0.326274 30 1 0 1.108729 0.755537 0.390549 31 6 0 0.365942-0.700110-0.936724 32 1 0 0.743978-1.722579-1.043298 33 6 0-0.041369-0.163038-2.322119 34 1 0-0.814616-0.792963-2.771934 35 1 0-0.423017 0.859071-2.243338 36 1 0 0.826624-0.168896-2.984837 37 6 0-0.811252-0.671819 0.053375 38 8 0-0.889343 0.211147 0.913634 39 7 0-1.750748-1.637736-0.084723 40 1 0-1.617812-2.362468-0.778862 41 6 0-2.815378-1.848471 0.911589 42 1 0-2.399530-1.539330 1.877062 43 6 0-3.199811-3.324150 0.958053 44 1 0-2.323722-3.928772 1.207815 45 1 0-3.959338-3.493279 1.723788 46 1 0-3.613292-3.660378 0.002765 47 6 0-4.042179-0.942683 0.639118 48 8 0-5.127840-1.429834 0.268124 49 6 0-4.652259 2.279544 2.090285 50 8 0-3.575581 2.376790 2.633679 51 8 0-5.745772 2.982949 2.428421 52 1 0-5.519627 3.576774 3.167014 53 7 0-3.855641 0.370267 0.858649 54 1 0-2.944911 0.672327 1.211111 55 6 0-4.933324 1.356657 0.899676 56 1 0-5.872256 0.834314 1.100935 57 6 0-5.058690 2.216598-0.386567 58 1 0-5.765299 3.026830-0.175431 59 1 0-4.085400 2.688954-0.562375 60 6 0-5.485691 1.502595-1.682708 61 1 0-5.321151 2.208757-2.503302 62 1 0-4.836225 0.644177-1.892735 63 6 0-6.957012 1.065991-1.779368 64 1 0-7.605590 1.871871-1.409682 65 1 0-7.205279 0.885266-2.832831 66 7 0-7.197147-0.162018-1.011332 67 1 0-6.386095-0.605198-0.545846 68 6 0-8.345164-0.827076-0.950251 69 7 0-9.464396-0.349302-1.519815 70 1 0-10.323969-0.877739-1.519431 71 1 0-9.475150 0.545531-1.983614 72 7 0-8.380523-2.008177-0.305793 73 1 0-7.537133-2.378939 0.111197 74 1 0-9.245779-2.498698-0.139301 Rotational constants (GHZ): 0.2014511 0.0296291 0.0282471 20

E[B3LYP/6-31+G(d,p)] = -2239.71478702 a.u. E[B3LYP/6-311++G(2d,p)] = -2240.24699745 a.u. E[MP2/6-311++G(2d,p)] = -2235.0516720243 a.u. ZPVE = 1616.5107 kj mol -1. Table S11. B3LYP/6-31+G(d,p) optimized structure of (ApSAAR + 2H) 2+ ion 2e 2+. Standard orientation: Center Atomic Atomic Coordinates (Angstroms) 1 7 0-7.993284 1.670489-0.968213 2 1 0-7.709303 1.742301-1.954505 3 1 0-8.886035 2.147574-0.826104 4 1 0-8.067285 0.642025-0.734601 5 6 0-6.880389 2.249080-0.122807 6 1 0-7.126907 2.005206 0.913511 7 6 0-6.757483 3.755732-0.335506 8 1 0-5.956346 4.151371 0.294491 9 1 0-6.515869 3.985729-1.377245 10 1 0-7.681799 4.270686-0.055305 11 6 0-5.644236 1.467869-0.615582 12 8 0-5.491162 1.326472-1.827344 13 7 0-4.843641 0.949591 0.336668 14 1 0-5.002254 1.136973 1.322019 15 6 0-3.744905 0.038915 0.051798 16 1 0-3.404024 0.217123-0.971291 17 6 0-4.198621-1.428994 0.198242 18 1 0-3.362930-2.105965 0.005951 19 1 0-4.580882-1.613651 1.205999 20 8 0-5.201640-1.748076-0.795674 21 6 0-2.646167 0.315651 1.099486 22 8 0-2.975036 0.644788 2.240136 23 15 0-6.752650-1.993937-0.513174 24 8 0-7.597428-0.826406-0.114421 25 8 0-7.266391-2.595762-1.892579 26 8 0-6.708874-3.151790 0.596140 27 1 0-6.747897-3.328499-2.261044 28 1 0-7.530511-3.255814 1.102307 29 7 0-1.370450 0.138831 0.700894 30 1 0-1.133514-0.143889-0.245588 31 6 0-0.241828 0.289834 1.614078 32 1 0-0.515461-0.180328 2.566564 33 6 0 0.104365 1.770685 1.870254 34 1 0-0.776066 2.280800 2.266113 35 1 0 0.904811 1.862837 2.610956 36 1 0 0.426342 2.262447 0.948148 37 6 0 0.935319-0.470229 0.982248 38 8 0 0.912002-0.841168-0.187576 39 7 0 2.024869-0.667844 1.789758 40 1 0 1.926050-0.479048 2.779605 41 6 0 3.133603-1.528862 1.375804 42 1 0 2.737189-2.278914 0.683870 43 6 0 3.755333-2.225247 2.595221 21

44 1 0 4.130442-1.497043 3.323303 45 1 0 3.012367-2.860190 3.085349 46 1 0 4.588733-2.855498 2.279800 47 6 0 4.216291-0.796814 0.567487 48 8 0 5.073391-1.470909-0.036347 49 6 0 4.088571 2.483245-0.838648 50 8 0 3.014177 2.760117-0.348538 51 8 0 4.629546 3.113757-1.889948 52 1 0 4.028461 3.824937-2.176184 53 7 0 4.205480 0.546761 0.577802 54 1 0 3.399459 1.002437 0.996125 55 6 0 5.013375 1.386242-0.302849 56 1 0 5.342920 0.782084-1.153028 57 6 0 6.229102 2.049989 0.400849 58 1 0 6.671633 2.761137-0.305283 59 1 0 5.840501 2.641210 1.238078 60 6 0 7.332334 1.125082 0.948316 61 1 0 7.975214 1.744528 1.582256 62 1 0 6.911726 0.359447 1.611182 63 6 0 8.257705 0.456674-0.082157 64 1 0 8.552554 1.188716-0.846252 65 1 0 9.165625 0.115272 0.430600 66 7 0 7.602153-0.694049-0.714674 67 1 0 6.635835-0.923020-0.422516 68 6 0 8.181725-1.572126-1.524964 69 7 0 9.435619-1.393409-1.974507 70 1 0 9.904687-2.098695-2.522726 71 1 0 9.964013-0.568505-1.737234 72 7 0 7.491639-2.665998-1.897228 73 1 0 6.554950-2.812176-1.543092 74 1 0 7.833382-3.293698-2.608542 Rotational constants (GHZ): 0.1918086 0.0277918 0.0263709 E[B3LYP/6-31+G(d,p)] = -2239.71451169 a.u. E[B3LYP/6-311++G(2d,p)] = -2240.24736292 a.u. E[MP2/6-311++G(2d,p)] = -2235.0497392568 a.u. ZPVE = 1615.2827 kj mol -1. Table S12. B3LYP/6-31+G(d,p) optimized structure of (AApSAR + 2H) 2+ ion 3a 2+. Standard orientation: Center Atomic Atomic Coordinates (Angstroms) 1 7 0-6.466640-1.442266-1.663159 2 1 0-5.829308-1.403476-2.470901 3 1 0-7.239528-2.083084-1.851875 4 1 0-5.891054-1.795528-0.838637 5 6 0-6.943161-0.034015-1.396394 6 1 0-7.589136 0.242804-2.237142 7 6 0-7.716426 0.036510-0.083127 8 1 0-8.566781-0.652094-0.099417 9 1 0-7.085090-0.214950 0.773305 10 1 0-8.136754 1.036899 0.054074 11 6 0-5.648886 0.805158-1.524224 22

12 8 0-4.795078 0.433214-2.329793 13 7 0-5.523569 1.907686-0.753107 14 1 0-6.174176 2.048798 0.008714 15 6 0-4.229044 2.588484-0.634189 16 1 0-3.796079 2.634840-1.636187 17 6 0-4.413313 3.996414-0.060934 18 1 0-3.449410 4.507509 0.009283 19 1 0-5.063995 4.582976-0.714408 20 1 0-4.850122 3.957461 0.941558 21 6 0-3.347394 1.722986 0.287112 22 8 0-3.808299 1.343163 1.378109 23 7 0-2.111411 1.415803-0.148896 24 1 0-1.807338 1.714830-1.069576 25 6 0-1.201349 0.541321 0.578451 26 1 0-1.488865 0.569313 1.631500 27 6 0-1.267821-0.917587 0.049091 28 1 0-0.811745-0.977432-0.940109 29 1 0-0.736862-1.596120 0.722578 30 8 0-2.628353-1.348185-0.141764 31 6 0 0.225407 1.084972 0.375327 32 8 0 0.571515 1.520391-0.715937 33 15 0-3.581111-1.975888 0.981722 34 8 0-4.968439-2.114610 0.435863 35 8 0-2.850225-3.343360 1.365548 36 8 0-3.439912-1.091643 2.291331 37 1 0-3.348615-3.935037 1.950139 38 1 0-3.656881-0.130115 2.114469 39 7 0 1.071780 1.012771 1.447905 40 1 0 0.681474 0.800258 2.357868 41 6 0 2.385058 1.667190 1.412243 42 1 0 2.288934 2.596958 0.842641 43 6 0 2.862402 1.980032 2.837340 44 1 0 3.838362 2.467928 2.801929 45 1 0 2.162074 2.660947 3.329252 46 1 0 2.953309 1.070055 3.440560 47 6 0 3.448249 0.861868 0.649277 48 8 0 4.461050 1.450852 0.230156 49 6 0 2.985739-2.193896-1.125719 50 8 0 1.823428-2.302345-0.789926 51 8 0 3.537439-2.833109-2.163171 52 1 0 2.864936-3.396955-2.586157 53 7 0 3.247571-0.460600 0.511451 54 1 0 2.338321-0.821482 0.783252 55 6 0 4.008486-1.324795-0.386805 56 1 0 4.509264-0.697988-1.130849 57 6 0 5.035167-2.239958 0.334528 58 1 0 4.482840-2.843231 1.064430 59 1 0 5.434978-2.938171-0.408775 60 6 0 6.203220-1.559231 1.072661 61 1 0 5.836812-0.807528 1.782031 62 1 0 6.681415-2.332747 1.682350 63 6 0 7.315506-0.945802 0.205816 64 1 0 8.209207-0.809066 0.827403 65 1 0 7.571691-1.633951-0.611284 66 7 0 6.907470 0.354096-0.340752 67 1 0 5.967738 0.708663-0.094746 68 6 0 7.690545 1.201660-0.999676 23

69 7 0 7.216726 2.424608-1.299757 70 1 0 6.289212 2.693387-0.997861 71 1 0 7.726372 3.062822-1.891261 72 7 0 8.937707 0.864113-1.368198 73 1 0 9.306887-0.056191-1.187086 74 1 0 9.557834 1.530731-1.803270 Rotational constants (GHZ): 0.1953918 0.0384256 0.0358455 E[B3LYP/6-31+G(d,p)] = -2239.72063643 a.u. E[B3LYP/6-311++G(2d,p)] = -2240.25266579 a.u. E[MP2/6-311++G(2d,p)] = -2235.0604602964 a.u. ZPVE = 1617.6018 kj mol -1. Table S13. B3LYP/6-31+G(d,p) optimized structure of (AApSAR + 2H) 2+ ion 3b 2+. Standard orientation: Center Atomic Atomic Coordinates (Angstroms) 1 7 0 6.994584 0.334078 1.240476 2 1 0 7.990975 0.179975 1.405614 3 1 0 6.584997-0.483634 0.692159 4 1 0 6.487635 0.372744 2.135717 5 6 0 6.729887 1.630285 0.511811 6 1 0 7.238339 2.417902 1.079164 7 6 0 7.267936 1.568477-0.914521 8 1 0 6.760766 0.802146-1.506880 9 1 0 7.156512 2.541047-1.402456 10 1 0 8.340039 1.349277-0.912107 11 6 0 5.209658 1.842896 0.708568 12 8 0 4.702406 1.455045 1.761311 13 7 0 4.513936 2.450440-0.278277 14 1 0 4.951359 2.575459-1.181850 15 6 0 3.046136 2.447324-0.259168 16 1 0 2.736342 2.676462 0.763022 17 6 0 2.490825 3.487134-1.235463 18 1 0 2.845871 4.483797-0.960931 19 1 0 2.799296 3.264249-2.261380 20 1 0 1.397989 3.488680-1.201437 21 6 0 2.592510 1.026579-0.645168 22 8 0 3.046323 0.508983-1.681303 23 7 0 1.726710 0.411374 0.180250 24 1 0 1.414196 0.874155 1.027231 25 6 0 1.264078-0.953372-0.016342 26 1 0 1.365130-1.188531-1.078055 27 6 0 2.086302-1.966512 0.830648 28 1 0 1.838509-1.850898 1.887706 29 1 0 1.864854-2.991809 0.518632 30 8 0 3.496547-1.702649 0.753696 31 6 0-0.205121-1.019535 0.434269 32 8 0-0.565004-0.375290 1.423477 33 15 0 4.492934-2.226036-0.387727 34 8 0 5.825491-1.564835-0.216979 35 8 0 4.471285-3.809839-0.191756 36 8 0 3.785033-2.005714-1.789461 24

37 1 0 5.109694-4.312238-0.721298 38 1 0 3.535482-1.045879-1.933175 39 7 0-1.028269-1.815914-0.286688 40 1 0-0.659940-2.232080-1.131889 41 6 0-2.416353-2.181445 0.066438 42 1 0-2.709820-2.927583-0.674263 43 6 0-2.535442-2.814018 1.464936 44 1 0-3.567746-3.134030 1.631315 45 1 0-1.895258-3.698297 1.524440 46 1 0-2.247459-2.115720 2.252243 47 6 0-3.448524-1.051552-0.127367 48 8 0-4.526435-1.327382-0.693653 49 6 0-3.067144 2.476108-0.357809 50 8 0-1.856590 2.454544-0.305764 51 8 0-3.786716 3.506007-0.834037 52 1 0-3.179686 4.216009-1.108739 53 7 0-3.165339 0.164888 0.365040 54 1 0-2.266907 0.293042 0.836249 55 6 0-3.985053 1.346803 0.123059 56 1 0-4.667791 1.121874-0.700446 57 6 0-4.782436 1.811260 1.371891 58 1 0-4.058998 2.018178 2.169223 59 1 0-5.259760 2.766116 1.127647 60 6 0-5.837989 0.839027 1.931369 61 1 0-5.402088-0.149905 2.117829 62 1 0-6.131009 1.222192 2.914261 63 6 0-7.139468 0.683524 1.127048 64 1 0-7.902837 0.241064 1.778929 65 1 0-7.496314 1.671735 0.806158 66 7 0-6.950962-0.184476-0.042680 67 1 0-6.007999-0.562357-0.228490 68 6 0-7.916219-0.643389-0.832606 69 7 0-7.608140-1.555949-1.772299 70 1 0-8.270875-1.834445-2.479588 71 1 0-6.657614-1.894019-1.850720 72 7 0-9.185378-0.220813-0.708644 73 1 0-9.932316-0.630203-1.249733 74 1 0-9.437787 0.492133-0.042227 Rotational constants (GHZ): 0.2001604 0.0388666 0.0350043 E[B3LYP/6-31+G(d,p)] = -2239.71846072 a.u. E[B3LYP/6-311++G(2d,p)] = -2240.25062357 a.u. E[MP2/6-311++G(2d,p)] = -2235.0586765391 a.u. ZPVE = 1618.5916 kj mol -1. Table S14. B3LYP/6-31+G(d,p) optimized structure of (AApSAR + 2H) 2+ ion 3c 2+. Standard orientation: Center Atomic Atomic Coordinates (Angstroms) 1 7 0 6.373296 1.036390-2.133434 2 1 0 5.755849 0.600191-2.832237 3 1 0 7.101020 1.584238-2.596128 4 1 0 5.758933 1.671884-1.539946 25

5 6 0 6.946497-0.072192-1.282119 6 1 0 7.620317-0.646281-1.928004 7 6 0 7.708636 0.499463-0.090698 8 1 0 8.202297-0.304646 0.462322 9 1 0 8.504034 1.170336-0.429491 10 1 0 7.051527 1.055983 0.583053 11 6 0 5.717373-0.969080-0.999091 12 8 0 4.848161-1.050766-1.867793 13 7 0 5.660059-1.624405 0.180778 14 1 0 6.310104-1.374397 0.914534 15 6 0 4.417158-2.279597 0.604835 16 1 0 4.018697-2.808937-0.263828 17 6 0 4.688466-3.255877 1.752582 18 1 0 5.403712-4.017656 1.432302 19 1 0 5.085880-2.732429 2.627355 20 1 0 3.764597-3.759253 2.049647 21 6 0 3.445525-1.164928 1.039157 22 8 0 3.834214-0.310487 1.854960 23 7 0 2.213272-1.173874 0.496439 24 1 0 1.967232-1.873213-0.196609 25 6 0 1.212380-0.149541 0.760406 26 1 0 1.452338 0.308016 1.722120 27 6 0 1.192870 0.934102-0.352243 28 1 0 0.775287 0.511765-1.268494 29 1 0 0.585636 1.788970-0.037787 30 8 0 2.516900 1.356411-0.716019 31 6 0-0.159286-0.849207 0.800270 32 8 0-0.405901-1.749523-0.003825 33 15 0 3.394397 2.470548 0.031593 34 8 0 4.786447 2.452032-0.517340 35 8 0 2.568543 3.814921-0.221908 36 8 0 3.257195 2.231733 1.592532 37 1 0 3.009872 4.634502 0.050045 38 1 0 3.547688 1.309199 1.857800 39 7 0-1.053090-0.416256 1.722247 40 1 0-0.766870 0.281583 2.397666 41 6 0-2.298217-1.153594 2.011536 42 1 0-2.079007-2.211648 1.827680 43 6 0-2.691640-0.948905 3.471369 44 1 0-3.588790-1.525068 3.705275 45 1 0-1.886331-1.293289 4.125973 46 1 0-2.908983 0.101925 3.683604 47 6 0-3.444734-0.759761 1.045807 48 8 0-4.446705-0.146623 1.461645 49 6 0-4.274264-2.420068-2.026447 50 8 0-3.313188-3.154740-2.025287 51 8 0-5.395438-2.627634-2.736755 52 1 0-5.295284-3.452687-3.245313 53 7 0-3.292631-1.153127-0.230462 54 1 0-2.464717-1.704986-0.466852 55 6 0-4.354427-1.109893-1.234851 56 1 0-5.318538-1.096070-0.719443 57 6 0-4.251799 0.085375-2.219806 58 1 0-3.254278 0.053382-2.672902 59 1 0-4.967791-0.091363-3.029929 60 6 0-4.477393 1.499418-1.652255 61 1 0-3.817074 1.693105-0.798191 26

62 1 0-4.174140 2.206647-2.431355 63 6 0-5.921855 1.867786-1.273776 64 1 0-6.006511 2.960017-1.211671 65 1 0-6.608210 1.516422-2.056282 66 7 0-6.294881 1.282248 0.019793 67 1 0-5.568923 0.752022 0.531962 68 6 0-7.447320 1.469218 0.653182 69 7 0-7.595120 0.977151 1.897186 70 1 0-6.829014 0.486477 2.338503 71 1 0-8.485158 0.987111 2.371462 72 7 0-8.460827 2.141237 0.082030 73 1 0-8.394965 2.484257-0.863466 74 1 0-9.316568 2.331212 0.581861 Rotational constants (GHZ): 0.1717187 0.0383126 0.0367195 E[B3LYP/6-31+G(d,p)] = -2239.7166801 a.u. E[B3LYP/6-311++G(2d,p)] = -2240.24879406 a.u. E[MP2/6-311++G(2d,p)] = -2235.0552994794 a.u. ZPVE = 1617.210 kj mol -1. Table S15. B3LYP/6-31+G(d,p) optimized structure of (AApSAR + 2H) 2+ ion 3d 2+. Standard orientation: Center Atomic Atomic Coordinates (Angstroms) 1 7 0 6.578496-0.042076-2.299725 2 1 0 7.282682 0.367354-2.916334 3 1 0 5.802367 0.651013-2.094055 4 1 0 6.129369-0.847452-2.756070 5 6 0 7.164315-0.524532-0.992012 6 1 0 7.945452-1.248648-1.248014 7 6 0 7.754459 0.638027-0.200730 8 1 0 8.258785 0.263992 0.694969 9 1 0 8.519912 1.155982-0.786856 10 1 0 6.991486 1.364285 0.092671 11 6 0 5.995339-1.321799-0.365625 12 8 0 5.274636-1.974495-1.121251 13 7 0 5.824219-1.261584 0.971872 14 1 0 6.378165-0.619318 1.522935 15 6 0 4.631650-1.838712 1.610331 16 1 0 4.395652-2.754907 1.064516 17 6 0 4.899953-2.143717 3.082998 18 1 0 4.016423-2.596131 3.541227 19 1 0 5.730143-2.848870 3.173179 20 1 0 5.134439-1.230471 3.637205 21 6 0 3.493291-0.810366 1.444773 22 8 0 3.528023 0.266984 2.065895 23 7 0 2.516076-1.134052 0.581108 24 1 0 2.561397-2.008922 0.064399 25 6 0 1.342355-0.315370 0.296166 26 1 0 1.102455 0.270293 1.189081 27 6 0 1.553557 0.663265-0.885646 28 1 0 2.156545 0.195999-1.667948 29 1 0 0.588145 0.962584-1.300722 27

30 8 0 2.168703 1.884168-0.432094 31 6 0 0.210241-1.301397-0.059070 32 8 0 0.472615-2.347808-0.646741 33 15 0 3.714435 2.287564-0.620451 34 8 0 4.451424 1.322544-1.495498 35 8 0 3.735902 3.752243-1.240868 36 8 0 4.257118 2.492639 0.855171 37 1 0 3.507875 4.467840-0.627288 38 1 0 3.990849 1.743293 1.460484 39 7 0-1.051130-0.927645 0.272047 40 1 0-1.228554-0.105333 0.836154 41 6 0-2.188699-1.801912-0.001990 42 1 0-2.029399-2.242008-0.991611 43 6 0-2.312974-2.941679 1.033584 44 1 0-1.394917-3.532506 1.023657 45 1 0-2.468533-2.537861 2.038381 46 1 0-3.146455-3.605953 0.787444 47 6 0-3.464817-0.959096-0.006960 48 8 0-3.549417 0.078582 0.683885 49 6 0-6.711450-2.298550-0.682814 50 8 0-6.274926-3.380123-1.009476 51 8 0-7.978297-2.060074-0.319106 52 1 0-8.485985-2.890331-0.375950 53 7 0-4.472075-1.440265-0.755210 54 1 0-4.343070-2.337344-1.217644 55 6 0-5.869801-1.016264-0.669224 56 1 0-6.027822-0.519612 0.291268 57 6 0-6.314973-0.099835-1.838912 58 1 0-6.122581-0.640111-2.772860 59 1 0-7.401152 0.023690-1.768155 60 6 0-5.649484 1.284707-1.942226 61 1 0-4.556092 1.197251-1.940478 62 1 0-5.911342 1.694455-2.923146 63 6 0-6.085626 2.333559-0.907856 64 1 0-5.773116 3.326581-1.255348 65 1 0-7.179628 2.330517-0.818409 66 7 0-5.487879 2.067349 0.408563 67 1 0-4.737274 1.360779 0.460075 68 6 0-5.798910 2.688737 1.540893 69 7 0-5.212769 2.292639 2.686818 70 1 0-4.560846 1.520392 2.679352 71 1 0-5.329495 2.804255 3.548148 72 7 0-6.693892 3.689458 1.569745 73 1 0-7.101990 4.053784 0.722897 74 1 0-6.994541 4.103521 2.439661 Rotational constants (GHZ): 0.1662900 0.0355778 0.0328156 E[B3LYP/6-31+G(d,p)] = -2239.71456844 a.u. E[B3LYP/6-311++G(2d,p)] = -2240.24693153 a.u. E[MP2/6-311++G(2d,p)] = -2235.0509797598 a.u. ZPVE = 1617.1285 kj mol -1. Table S16. B3LYP/6-31+G(d,p) optimized structure of (AApSAR + 2H) 2+ ion 3e 2+. Standard orientation: 28

Center Atomic Atomic Coordinates (Angstroms) 1 7 0 2.214751-2.388805-1.652555 2 1 0 2.240644-2.895901-2.540422 3 1 0 2.811472-1.514978-1.738273 4 1 0 1.236882-2.074341-1.478223 5 6 0 2.755337-3.251805-0.528656 6 1 0 2.111750-4.134236-0.471446 7 6 0 4.193494-3.660632-0.829536 8 1 0 4.231965-4.281064-1.730209 9 1 0 4.843544-2.795659-0.993270 10 1 0 4.590845-4.265673-0.010120 11 6 0 2.479143-2.451524 0.761060 12 8 0 1.298158-2.297271 1.118104 13 7 0 3.515058-1.912435 1.416407 14 1 0 4.445442-2.015162 1.029957 15 6 0 3.361318-0.954188 2.532153 16 1 0 2.447620-1.237330 3.060688 17 6 0 4.562921-1.015480 3.466495 18 1 0 5.485797-0.738768 2.949478 19 1 0 4.427868-0.312124 4.291456 20 1 0 4.664788-2.020629 3.883251 21 6 0 3.180803 0.451020 1.893484 22 8 0 4.134014 1.221379 1.744842 23 7 0 1.925623 0.698100 1.461348 24 1 0 1.187869 0.050305 1.729412 25 6 0 1.444168 1.889142 0.774431 26 1 0 1.874762 2.786598 1.237431 27 6 0 1.777214 1.908311-0.737419 28 1 0 1.512213 0.948040-1.188176 29 1 0 1.217471 2.699862-1.240151 30 8 0 3.156168 2.216491-0.963455 31 6 0-0.094491 1.873277 0.975580 32 8 0-0.627697 0.996722 1.650496 33 15 0 4.263794 1.162074-1.470146 34 8 0 3.726650-0.236752-1.502160 35 8 0 4.744113 1.607403-2.917136 36 8 0 5.507772 1.449422-0.540240 37 1 0 5.336970 2.375542-2.946934 38 1 0 5.241837 1.479380 0.413650 39 7 0-0.839711 2.796109 0.300246 40 1 0-0.389531 3.611036-0.097505 41 6 0-2.292823 2.872578 0.513088 42 1 0-2.497095 3.044326 1.575365 43 6 0-2.889419 4.017434-0.316083 44 1 0-2.459351 4.974770-0.006383 45 1 0-2.709087 3.879055-1.387022 46 1 0-3.967298 4.070747-0.149349 47 6 0-2.991610 1.535189 0.217910 48 8 0-4.033215 1.254633 0.829939 49 6 0-1.346412-1.397001-0.582511 50 8 0-0.398352-1.146844-1.329720 51 8 0-1.292441-2.228197 0.435470 52 1 0-0.346195-2.469055 0.631752 53 7 0-2.466992 0.725910-0.734553 54 1 0-1.612763 1.033598-1.184918 29

55 6 0-2.715010-0.723683-0.755526 56 1 0-3.305619-0.961963 0.129160 57 6 0-3.415531-1.215659-2.040239 58 1 0-2.768848-0.974235-2.891094 59 1 0-3.475640-2.310784-1.995504 60 6 0-4.815895-0.635423-2.319501 61 1 0-4.787027 0.460623-2.296063 62 1 0-5.073731-0.903655-3.348993 63 6 0-5.976838-1.134744-1.442363 64 1 0-6.918928-0.884567-1.946188 65 1 0-5.925484-2.227319-1.339880 66 7 0-5.961064-0.509151-0.114334 67 1 0-5.207445 0.154370 0.114605 68 6 0-6.883839-0.661080 0.833025 69 7 0-6.740694 0.010483 1.988387 70 1 0-7.415773-0.061058 2.734151 71 1 0-5.945269 0.622848 2.120675 72 7 0-7.939313-1.472995 0.658901 73 1 0-8.648476-1.575492 1.369584 74 1 0-8.083225-1.969000-0.206714 Rotational constants (GHZ): 0.1655631 0.0535851 0.0500317 E[B3LYP/6-31+G(d,p)] = -2239.7135251 a.u. E[B3LYP/6-311++G(2d,p)] = -2240.24451798 a.u. E[MP2/6-311++G(2d,p)] = -2235.0596990416 a.u. ZPVE = 1620.2246 kj mol -1. Table S17. B3LYP/6-31+G(d,p) optimized structure of (AAApSR + 2H) 2+ ion 4a 2+. Standard orientation: Center Atomic Atomic Coordinates (Angstroms) 1 7 0 4.176306 1.624957 2.637785 2 1 0 3.325749 1.909365 2.058919 3 1 0 4.997734 2.029104 2.164683 4 1 0 4.099965 1.992546 3.587896 5 6 0 4.339931 0.124586 2.613672 6 1 0 5.179053-0.108377 3.278918 7 6 0 3.069465-0.568628 3.096924 8 1 0 2.793135-0.214674 4.094992 9 1 0 3.237762-1.645154 3.193237 10 1 0 2.228408-0.396984 2.420330 11 6 0 4.820074-0.156044 1.167364 12 8 0 5.498572 0.702805 0.609469 13 7 0 4.477106-1.340896 0.611775 14 1 0 3.852973-1.957412 1.115818 15 6 0 4.754674-1.660063-0.798765 16 1 0 5.508212-0.942165-1.129640 17 6 0 5.278661-3.087723-0.951270 18 1 0 4.598925-3.835076-0.524296 19 1 0 6.234284-3.183249-0.430378 20 1 0 5.445122-3.327953-2.005088 21 6 0 3.466437-1.309811-1.570430 22 8 0 3.171709-0.129137-1.816618 30

23 7 0 2.611079-2.300163-1.890583 24 1 0 2.829451-3.256415-1.645777 25 6 0 1.254139-1.998599-2.356282 26 1 0 1.337538-1.316380-3.207616 27 6 0 0.543744-3.286459-2.780504 28 1 0-0.456324-3.059742-3.159115 29 1 0 1.101036-3.779843-3.581704 30 1 0 0.441476-3.972289-1.934075 31 6 0 0.501899-1.304570-1.198555 32 8 0 0.450689-1.818083-0.078421 33 7 0-0.107159-0.118864-1.478270 34 1 0 0.156570 0.348295-2.337649 35 6 0-0.569005 0.737976-0.379010 36 1 0 0.065158 0.522522 0.487406 37 6 0-0.418075 2.217830-0.747825 38 1 0-1.105356 2.501301-1.546071 39 1 0-0.622820 2.840704 0.125973 40 8 0 0.902724 2.465759-1.270381 41 6 0-2.029025 0.427926 0.015917 42 8 0-2.949206 1.231694-0.238224 43 15 0 2.195714 2.784775-0.360298 44 8 0 2.121166 2.122549 0.989002 45 8 0 2.288063 4.367092-0.176913 46 8 0 3.403651 2.430034-1.299096 47 1 0 2.532194 4.865871-0.973098 48 1 0 3.491350 1.457999-1.519317 49 6 0-3.108004-1.717398 2.661928 50 8 0-1.986056-1.996906 3.020389 51 8 0-4.210933-1.874752 3.411535 52 1 0-3.956773-2.259428 4.269755 53 7 0-2.207701-0.740687 0.649878 54 1 0-1.377734-1.308292 0.834973 55 6 0-3.457671-1.156336 1.278825 56 1 0-4.074252-0.267152 1.434708 57 6 0-4.240942-2.220522 0.465169 58 1 0-3.577347-3.081227 0.322669 59 1 0-5.073741-2.568339 1.085576 60 6 0-4.774031-1.794991-0.915545 61 1 0-3.974337-1.362998-1.529781 62 1 0-5.084931-2.708195-1.433463 63 6 0-5.993873-0.859834-0.929758 64 1 0-6.449003-0.890410-1.927896 65 1 0-6.737874-1.213080-0.203456 66 7 0-5.614095 0.523990-0.614771 67 1 0-4.610651 0.740004-0.511295 68 6 0-6.447636 1.556828-0.539987 69 7 0-7.769926 1.404200-0.716180 70 1 0-8.170324 0.505243-0.934774 71 1 0-8.406653 2.183404-0.639365 72 7 0-5.950173 2.777840-0.270298 73 1 0-4.953730 2.902154-0.154310 74 1 0-6.535624 3.598620-0.245724 Rotational constants (GHZ): 0.1430032 0.0541213 0.0501733 E[B3LYP/6-31+G(d,p)] = -2239.71297355 a.u. E[B3LYP/6-311++G(2d,p)] = -2240.24471162 a.u. 31

E[MP2/6-311++G(2d,p)] = -2235.0558265269 a.u. ZPVE = 1618.9462 kj mol -1. Table S18. B3LYP/6-31+G(d,p) optimized structure of (AAApSR + 2H) 2+ ion 4b 2+. Standard orientation: Center Atomic Atomic Coordinates (Angstroms) 1 7 0 5.175465-2.727307-0.236951 2 1 0 5.384656-2.602789 0.765992 3 1 0 5.501111-3.643315-0.551460 4 1 0 4.120447-2.673388-0.353883 5 6 0 5.859873-1.595620-0.966378 6 1 0 6.931181-1.825901-0.959643 7 6 0 5.349342-1.483833-2.399230 8 1 0 4.287794-1.225244-2.429524 9 1 0 5.488757-2.429015-2.932632 10 1 0 5.926628-0.734735-2.948909 11 6 0 5.661121-0.385913-0.017778 12 8 0 5.644566-0.601626 1.192412 13 7 0 5.551821 0.842292-0.573103 14 1 0 5.434612 0.909115-1.575254 15 6 0 5.111535 1.987978 0.217001 16 1 0 5.613221 1.914383 1.188756 17 6 0 5.502485 3.299122-0.474815 18 1 0 5.288158 4.165091 0.157123 19 1 0 4.972144 3.432475-1.423429 20 1 0 6.577961 3.305095-0.667170 21 6 0 3.596884 1.830659 0.504044 22 8 0 3.038347 0.740331 0.290093 23 7 0 2.920338 2.873871 1.006461 24 1 0 3.370495 3.775394 1.088167 25 6 0 1.489987 2.786821 1.327972 26 1 0 1.367787 2.046339 2.127577 27 6 0 0.986318 4.150810 1.809906 28 1 0 1.549830 4.479227 2.688430 29 1 0 1.078708 4.896947 1.015467 30 1 0-0.066565 4.082799 2.094234 31 6 0 0.703277 2.336103 0.074657 32 8 0 0.830511 2.902708-1.000639 33 7 0-0.173742 1.297252 0.276671 34 1 0-0.035269 0.718731 1.096880 35 6 0-0.846299 0.684848-0.866139 36 1 0-0.945861 1.480093-1.612370 37 6 0-0.005703-0.418360-1.541473 38 1 0-0.445896-0.695241-2.502791 39 1 0 1.001994-0.035079-1.716164 40 8 0 0.041740-1.650108-0.772780 41 6 0-2.284661 0.320176-0.436764 42 8 0-3.125286 1.222355-0.279090 43 15 0 1.269872-2.162105 0.160511 44 8 0 2.516229-2.480772-0.602099 45 8 0 0.619325-3.413250 0.867427 46 8 0 1.459749-1.053677 1.287586 47 1 0-0.288545-3.294322 1.215224 32