1

Silver(I)-mediated Hoogsteen-type base pairs

Dominik A. Megger,a Célia Fonseca Guerra,b F. Matthias Bickelhaupt,*b and Jens

Müller*a

a) University of Muenster, Institute for Inorganic and Analytical Chemistry,

Corrensstr. 28/30, 48149 Muenster, Germany

b) Department of Theoretical Chemistry and Amsterdam Center for Multiscale

Modeling (ACMM), Scheikundig Laboratorium der Vrije Universiteit, De Boelelaan

1083, 1081 HV Amsterdam, The Netherlands.

mueller.j@uni-muenster.de, phone: +49 251 833 6006, fax: +49 251 833 6007

f.m.bickelhaupt@vu.nl, phone: +31 20 59 87617, fax: +31 20 59 87629

SUPPLEMENTARY INFORMATION

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Figure S1. Geometry-optimized structures (in water) of silver(I)-mediated Hoogsteen-type base pairs containing artificial 1-deazapurine-derived nucleobases.

  3

Figure S2. Two views of a tilted C–Ag+–G base pair.

  4

Figure S3. Plot of ΔEComplex (kcal mol–1) as a function of the VDD atomic charge (a.u.) of N7.

  5

Figure S4. Selected geometry-optimized structures (in water) of silver(I)-mediated reverse Hoogsteen-type base pairs containing artificial 1-deazapurine-derived nucleobases.

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Table S1. Cartesian coordinates (a.u.) and total bonding energies (kcal mol–1) of the geometry-optimized structures of silver(I)-mediated base pairs. C*–Ag–C (gas phase), -3737.5942 N -3.395579 -0.111987 -0.060009 C -3.994452 -1.327361 0.271419 N -5.398415 -1.314141 0.364806 C -6.154863 -0.198537 0.150932 C -5.560443 0.984453 -0.172197 C -4.129827 0.999949 -0.274663 N -3.481354 2.137172 -0.590680 O -3.361168 -2.363261 0.475288 AG -1.267152 -0.348311 -0.148732 H -7.228818 -0.314863 0.252742 N 0.685843 -1.220338 -0.071450 H -3.988778 2.995359 -0.760704 H -2.469067 2.148898 -0.663659 H -6.144831 1.880654 -0.345569 H -5.830584 -2.201637 0.606420 C 1.721504 -0.330469 -0.354047 N 3.022530 -0.877259 -0.310290 C 3.275988 -2.184542 -0.013910 C 0.916395 -2.518994 0.224398 C 2.252893 -3.042588 0.260321 O 1.534121 0.849597 -0.624148 H 3.777471 -0.229257 -0.516134 H 4.318065 -2.487082 -0.011169 N -0.134544 -3.320273 0.487016 H 2.438692 -4.083777 0.497516 H 0.016756 -4.295011 0.710169 H -1.094627 -2.975549 0.468755 C*–Ag–C (COSMO), -3797.4409 N -3.411400 -0.147800 -0.051100 C -4.036900 -1.335400 0.283400 N -5.428400 -1.308600 0.373000 C -6.171800 -0.186000 0.147100 C -5.559800 0.985000 -0.181500 C -4.130800 0.980200 -0.277500 N -3.470000 2.101800 -0.596900 O -3.412200 -2.393000 0.500300 AG -1.272600 -0.347100 -0.147900 H -7.244700 -0.295300 0.246100 N 0.713100 -1.180700 -0.079900 H -3.972100 2.962300 -0.774200 H -2.458000 2.106100 -0.665400 H -6.122400 1.891800 -0.365800 H -5.885300 -2.182000 0.616600 C 1.769000 -0.332700 -0.347900 N 3.049500 -0.889200 -0.305000 C 3.284100 -2.203200 -0.018800 C 0.922000 -2.492700 0.211200 C 2.245000 -3.042000 0.246200 O 1.612400 0.872400 -0.616900 H 3.824800 -0.263300 -0.500000 H 4.321200 -2.515200 -0.018500 N -0.136900 -3.276700 0.467000 H 2.400500 -4.088900 0.476600 H 0.003400 -4.254000 0.689700 H -1.089700 -2.915400 0.461000

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C–Ag–C (gas phase), -3729.9909 N 0.000000 2.155952 0.388889 C 0.000000 2.670561 1.695109 N 0.000000 4.082014 1.794304 C 0.000000 4.913176 0.717110 C 0.000000 4.400188 -0.546997 C 0.000000 2.973220 -0.681743 N 0.000000 2.415039 -1.912139 O 0.000000 1.965390 2.690309 AG 0.000000 0.000000 0.416367 H 0.000000 5.978556 0.923622 N 0.000000 -2.155952 0.388889 H 0.000000 2.986750 -2.745751 H 0.000000 1.406171 -2.002572 H 0.000000 5.044537 -1.418335 H 0.000000 4.448263 2.742471 C 0.000000 -2.973220 -0.681743 C 0.000000 -4.400188 -0.546997 C 0.000000 -4.913176 0.717110 C 0.000000 -2.670561 1.695109 N 0.000000 -4.082014 1.794304 N 0.000000 -2.415039 -1.912139 H 0.000000 -5.044537 -1.418335 H 0.000000 -5.978556 0.923622 O 0.000000 -1.965390 2.690309 H 0.000000 -4.448263 2.742471 H 0.000000 -2.986750 -2.745751 H 0.000000 -1.406171 -2.002572 C–Ag–C (COSMO), -3796.7050 N 0.000000 2.155158 0.432671 C 0.000000 2.775806 1.669555 N 0.000000 4.172215 1.674132 C 0.000000 4.925593 0.536599 C 0.000000 4.320133 -0.682654 C 0.000000 2.888195 -0.711045 N 0.000000 2.243062 -1.886271 O 0.000000 2.141633 2.739412 AG 0.000000 0.000000 0.508061 H 0.000000 5.999855 0.672819 N 0.000000 -2.155158 0.432671 H 0.000000 2.756181 -2.758161 H 0.000000 1.230269 -1.917951 H 0.000000 4.889181 -1.604309 H 0.000000 4.622664 2.584203 C 0.000000 -2.888195 -0.711045 C 0.000000 -4.320133 -0.682654 C 0.000000 -4.925593 0.536599 C 0.000000 -2.775806 1.669555 N 0.000000 -4.172215 1.674132 N 0.000000 -2.243062 -1.886271 H 0.000000 -4.889181 -1.604309 H 0.000000 -5.999855 0.672819 O 0.000000 -2.141633 2.739412 H 0.000000 -4.622664 2.584203 H 0.000000 -2.756181 -2.758161 H 0.000000 -1.230269 -1.917951 C–Ag–G (gas phase), -4295.8877 N -3.124499 -0.359441 -0.009480

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C -4.120378 -1.337752 -0.041695 N -5.449408 -0.857939 -0.050169 C -5.768694 0.467958 -0.028441 C -4.787080 1.411962 0.002837 C -3.422666 0.959756 0.011704 N -2.416819 1.851453 0.041499 O -3.881105 -2.538237 -0.061698 AG -1.142830 -1.168530 0.002852 H -6.170799 -1.572677 -0.073649 H -6.825852 0.712598 -0.037613 N 2.838869 1.624693 0.075643 C 4.101029 1.047050 0.077272 N 4.298108 -0.263941 0.061392 C 3.152887 -0.971179 0.048266 C 1.840865 -0.491971 0.041186 C 1.599018 0.918591 0.057192 N 3.030114 -2.347785 0.032534 C 1.689662 -2.653742 0.016891 N 0.946912 -1.557011 0.021612 O 0.527225 1.536356 0.058649 N 5.169102 1.882650 0.120806 H 3.799774 -3.009206 0.033129 H 1.316369 -3.667236 0.002210 H -5.022274 2.469901 0.020252 H -2.628158 2.840229 0.057380 H -1.432063 1.572209 0.046258 H 2.745034 2.637840 0.108544 H 6.090117 1.467862 0.045605 H 5.076773 2.878785 -0.022881 C–Ag–G (COSMO), -4357.9269 N -3.151700 -0.403700 -0.011300 C -4.170700 -1.335400 -0.056400 N -5.477700 -0.843300 -0.066200 C -5.775700 0.488800 -0.033500 C -4.775600 1.410600 0.010800 C -3.424500 0.929500 0.020300 N -2.405500 1.798800 0.060500 O -3.961200 -2.562500 -0.087400 AG -1.143600 -1.175400 0.007800 H -6.222900 -1.532100 -0.098900 H -6.828000 0.744800 -0.046600 N 2.870600 1.633800 0.068300 C 4.126600 1.053000 0.067100 N 4.316900 -0.266200 0.057300 C 3.161900 -0.967000 0.050000 C 1.855500 -0.468100 0.045500 C 1.639000 0.941400 0.057500 N 3.023900 -2.337300 0.038800 C 1.685000 -2.628800 0.026200 N 0.949900 -1.525000 0.030100 O 0.560900 1.572000 0.059600 N 5.189200 1.891400 0.115400 H 3.777600 -3.016400 0.036500 H 1.305800 -3.638400 0.012500 H -4.980100 2.474200 0.036600 H -2.603200 2.791300 0.080500 H -1.426500 1.502400 0.061100 H 2.803800 2.649400 0.085100 H 6.107000 1.491900 -0.041800 H 5.068300 2.875300 -0.091300

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C–Ag–G (tilted), -4288.9725 N -3.208300 -0.789500 0.417600 C -3.981400 -0.623700 -0.733300 N -5.354800 -0.371600 -0.516800 C -5.916400 -0.290400 0.723500 C -5.150500 -0.454100 1.838100 C -3.748100 -0.711600 1.655400 N -2.948600 -0.879800 2.723200 O -3.521000 -0.688400 -1.865900 AG -1.142800 -1.168500 0.002900 H -5.913700 -0.251600 -1.356500 H -6.982700 -0.092500 0.761300 N 2.838900 1.624700 0.075600 C 4.101000 1.047100 0.077300 N 4.298100 -0.263900 0.061400 C 3.152900 -0.971200 0.048300 C 1.840900 -0.492000 0.041200 C 1.599000 0.918600 0.057200 N 3.030100 -2.347800 0.032500 C 1.689700 -2.653700 0.016900 N 0.946900 -1.557000 0.021600 O 0.527200 1.536400 0.058600 N 5.169100 1.882600 0.120800 H 3.799800 -3.009200 0.033100 H 1.316400 -3.667200 0.002200 H -5.579700 -0.392700 2.831500 H -3.341500 -0.823500 3.653300 H -1.945100 -1.062400 2.637700 H 2.745000 2.637800 0.108500 H 6.090100 1.467900 0.045600 H 5.076800 2.878800 -0.022900 C–Ag–1a (gas phase), -4210.4235 N -3.391776 -0.168374 -0.029440 C -4.297096 -1.211126 0.194864 N -5.662879 -0.845794 0.179926 C -6.098763 0.425701 -0.042425 C -5.204841 1.431850 -0.261881 C -3.810484 1.095467 -0.246263 N -2.881726 2.054095 -0.449610 O -3.952132 -2.367681 0.390458 AG -1.348238 -0.806286 -0.015869 H -7.172857 0.580028 -0.032353 C 2.772606 1.960574 0.351577 C 4.040294 1.348380 0.231172 C 4.179915 -0.020745 0.007623 C 2.990527 -0.752215 -0.086928 C 1.709313 -0.165655 0.031519 C 1.596369 1.218092 0.254433 N 2.737933 -2.109075 -0.284374 C 1.390648 -2.300773 -0.278062 N 0.733395 -1.161159 -0.091142 O 0.329498 1.776069 0.369566 H 4.927407 1.968408 0.315374 H 0.931007 -3.269908 -0.409422 H 0.427551 2.686016 0.703299 H 5.155569 -0.488549 -0.083470 H 2.709031 3.033722 0.523200 H -3.165486 3.003523 -0.649635 H -1.889686 1.831278 -0.430614

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H -5.532776 2.449789 -0.437784 H -6.318126 -1.605100 0.343388 H 3.431913 -2.837114 -0.405654 C–Ag–1a (COSMO), -4268.2986 N -3.403500 -0.207400 -0.025000 C -4.353500 -1.200200 0.127200 N -5.691700 -0.800200 0.114000 C -6.084100 0.497600 -0.042700 C -5.152600 1.478600 -0.194400 C -3.773200 1.091800 -0.180600 N -2.816300 2.020900 -0.324700 O -4.056800 -2.400200 0.271100 AG -1.348400 -0.843100 -0.008600 H -7.151600 0.679700 -0.036600 C 2.757300 2.002400 0.269000 C 4.031100 1.397900 0.155400 C 4.183000 0.020100 -0.015800 C 2.999400 -0.728700 -0.068600 C 1.712700 -0.149600 0.042000 C 1.586500 1.241400 0.214600 N 2.762000 -2.089200 -0.221800 C 1.421100 -2.295000 -0.203000 N 0.746900 -1.157900 -0.045300 O 0.322300 1.787100 0.327500 H 4.912600 2.030500 0.204100 H 0.975000 -3.272200 -0.306300 H 0.408900 2.747400 0.477400 H 5.159200 -0.446600 -0.102600 H 2.674200 3.078700 0.403100 H -3.069700 2.993000 -0.444600 H -1.830800 1.772800 -0.303500 H -5.432000 2.517700 -0.320000 H -6.385900 -1.532700 0.226300 H 3.462300 -2.813100 -0.331900 C–Ag–1a (tilted), -4208.2062 N -3.391800 -0.168400 -0.029400 C -3.867400 0.133500 -1.310000 N -5.208800 0.575900 -1.373000 C -6.006700 0.715700 -0.277600 C -5.528900 0.419800 0.964900 C -4.173100 -0.038500 1.062400 N -3.651300 -0.353400 2.267200 O -3.185400 0.031000 -2.319600 AG -1.348200 -0.806300 -0.015900 H -7.018100 1.066700 -0.454700 C 2.772600 1.960600 0.351600 C 4.040300 1.348400 0.231200 C 4.179900 -0.020700 0.007600 C 2.990500 -0.752200 -0.086900 C 1.709300 -0.165700 0.031500 C 1.596400 1.218100 0.254400 N 2.737900 -2.109100 -0.284400 C 1.390600 -2.300800 -0.278100 N 0.733400 -1.161200 -0.091100 O 0.329500 1.776100 0.369600 H 4.927400 1.968400 0.315400 H 0.931000 -3.269900 -0.409400 H 0.427600 2.686000 0.703300 H 5.155600 -0.488500 -0.083500

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H 2.709000 3.033700 0.523200 H -4.200700 -0.232900 3.107200 H -2.695000 -0.689500 2.349400 H -6.149700 0.522200 1.847400 H -5.551600 0.794100 -2.304400 H 3.431900 -2.837100 -0.405700 C–Ag–1b (gas phase), -4105.2599 N -3.410193 -0.171526 -0.027870 C -4.289403 -1.248317 0.135557 N -5.663588 -0.918101 0.132939 C -6.131548 0.351951 -0.021117 C -5.263336 1.391540 -0.181173 C -3.861248 1.090628 -0.178611 N -2.956043 2.081487 -0.327235 O -3.913897 -2.403878 0.271315 AG -1.355992 -0.772002 -0.023939 H -7.209362 0.477697 -0.007737 C 2.865880 1.920718 0.272840 C 4.078272 1.202510 0.189874 N 4.168246 -0.130154 0.035924 C 2.983067 -0.730021 -0.032280 C 1.700757 -0.139523 0.035192 C 1.639472 1.252955 0.195358 N 2.737866 -2.092783 -0.178989 C 1.390767 -2.280986 -0.193167 N 0.726437 -1.133007 -0.066992 O 0.413474 1.876603 0.268876 H 5.019405 1.743527 0.252006 H 0.930509 -3.253418 -0.294271 H 0.557869 2.819420 0.471231 H 2.891856 3.001581 0.397225 H -3.261119 3.034591 -0.470426 H -1.960442 1.878052 -0.325178 H -5.617373 2.408633 -0.303221 H -6.299729 -1.701674 0.252103 H 3.450262 -2.811414 -0.255806 C–Ag–1b (COSMO), -4166.7761 N -3.415400 -0.209100 0.001800 C -4.347800 -1.222600 -0.123000 N -5.692700 -0.846400 -0.120300 C -6.108200 0.448000 -0.000600 C -5.194300 1.449200 0.123700 C -3.808300 1.086800 0.122200 N -2.868100 2.036200 0.241300 O -4.029400 -2.420600 -0.234100 AG -1.352400 -0.820200 -0.001400 H -7.178900 0.610700 -0.013300 C 2.821300 1.971200 -0.063200 C 4.044100 1.280600 0.013200 N 4.169100 -0.063700 0.087700 C 2.992500 -0.702100 0.084100 C 1.701900 -0.129100 0.013100 C 1.608300 1.268200 -0.066500 N 2.771300 -2.069400 0.146100 C 1.429500 -2.281800 0.113300 N 0.744600 -1.142300 0.033300 O 0.380500 1.862400 -0.146500 H 4.970600 1.848900 0.012600 H 0.991400 -3.267100 0.148200

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H 0.496200 2.829100 -0.224700 H 2.813800 3.056300 -0.120600 H -3.137100 3.006600 0.340100 H -1.879600 1.801800 0.241500 H -5.492500 2.486300 0.219800 H -6.373900 -1.593900 -0.213000 H 3.482600 -2.790100 0.202600 C–Ag–1b (tilted), -4103.8030 N -3.410200 -0.171500 -0.027900 C -3.884500 0.127300 -1.310400 N -5.234600 0.539400 -1.379500 C -6.043100 0.652700 -0.289000 C -5.567100 0.359900 0.955100 C -4.201700 -0.065800 1.059100 N -3.678900 -0.374500 2.265300 O -3.193100 0.045100 -2.315400 AG -1.356000 -0.772000 -0.023900 H -7.061300 0.981100 -0.470900 C 2.865900 1.920700 0.272800 C 4.078300 1.202500 0.189900 N 4.168200 -0.130200 0.035900 C 2.983100 -0.730000 -0.032300 C 1.700800 -0.139500 0.035200 C 1.639500 1.253000 0.195400 N 2.737900 -2.092800 -0.179000 C 1.390800 -2.281000 -0.193200 N 0.726400 -1.133000 -0.067000 O 0.413500 1.876600 0.268900 H 5.019400 1.743500 0.252000 H 0.930500 -3.253400 -0.294300 H 0.557900 2.819400 0.471200 H 2.891900 3.001600 0.397200 H -4.236600 -0.279100 3.103100 H -2.712900 -0.678500 2.348600 H -6.196200 0.442500 1.833800 H -5.576600 0.755400 -2.311900 H 3.450300 -2.811400 -0.255800 C–Ag–2a (gas phase), -4568.6596 N -3.587286 2.117946 -0.247241 C -2.598963 -1.285430 0.158707 C -3.814091 -1.971671 0.230787 C -5.049875 -1.289489 0.130197 C -5.127281 0.089991 -0.040294 C -3.903149 0.767438 -0.104970 C -2.654488 0.115668 -0.010016 N -1.632246 1.068031 -0.092113 C -2.232460 2.245231 -0.232994 O -1.350673 -1.865037 0.246480 H -5.965385 -1.869980 0.190681 H -1.726544 3.195536 -0.325225 H -1.836202 -3.392181 1.605876 AG 0.427120 0.596426 -0.058345 O 3.154741 1.915914 0.482694 N 2.424266 -0.173106 -0.173756 C 2.744638 -1.428930 -0.545188 C 4.109069 -1.861365 -0.635939 C 5.079369 -0.955135 -0.323130 N 4.743218 0.308608 0.057467 C 3.408272 0.768307 0.147627

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N 1.741937 -2.291173 -0.825819 H 4.357424 -2.872502 -0.936979 H 6.139004 -1.186643 -0.358452 H 0.771422 -1.989935 -0.781818 H -3.822783 -3.047342 0.366171 C -1.308033 -3.258247 0.653740 H -1.759447 -3.897889 -0.116046 H -0.248214 -3.495243 0.776239 H 1.950706 -3.213380 -1.183205 H -4.246311 2.881822 -0.338426 H 5.455924 0.994379 0.290936 H -6.079597 0.606437 -0.113271 C–Ag–2a (COSMO), -4623.7193 N -3.606900 2.096900 -0.231600 C -2.600100 -1.300800 0.174500 C -3.813700 -1.997200 0.228200 C -5.053600 -1.319200 0.121500 C -5.135800 0.063200 -0.039700 C -3.913300 0.749000 -0.091000 C -2.661500 0.101800 0.010800 N -1.644500 1.059200 -0.068400 C -2.257200 2.232500 -0.213600 O -1.353400 -1.870300 0.276800 H -5.966500 -1.905700 0.169800 H -1.760500 3.186000 -0.306700 H -1.835000 -3.529200 1.475300 AG 0.430600 0.627400 -0.067900 O 3.244700 1.945900 0.422200 N 2.440700 -0.132800 -0.174600 C 2.719400 -1.420400 -0.508300 C 4.066700 -1.900800 -0.573400 C 5.064100 -1.019100 -0.287600 N 4.763400 0.269600 0.044800 C 3.456900 0.759100 0.114200 N 1.698200 -2.250400 -0.775500 H 4.272400 -2.930600 -0.839300 H 6.115900 -1.276500 -0.305300 H 0.736400 -1.924000 -0.746800 H -3.814700 -3.073700 0.355400 C -1.303800 -3.300800 0.543900 H -1.750200 -3.857700 -0.288500 H -0.243900 -3.541400 0.643800 H 1.882000 -3.201900 -1.065700 H -4.269500 2.857100 -0.329700 H 5.507300 0.928000 0.255800 H -6.086300 0.581400 -0.118700 C–Ag–2a (tilted), -4566.9771 N -3.682900 1.667200 -0.712100 C -2.245600 0.410900 2.301200 C -3.330100 0.353100 3.180600 C -4.629000 0.737600 2.771100 C -4.899300 1.194900 1.484300 C -3.803500 1.254200 0.614000 C -2.496800 0.876000 0.991600 N -1.632200 1.068000 -0.092100 C -2.380100 1.539500 -1.084300 O -0.949200 0.057600 2.611500 H -5.437400 0.672000 3.492800 H -2.018400 1.796200 -2.069500

  14

H -0.954200 0.675300 4.620000 AG 0.427100 0.596400 -0.058300 O 3.154700 1.915900 0.482700 N 2.424300 -0.173100 -0.173800 C 2.744600 -1.428900 -0.545200 C 4.109100 -1.861400 -0.635900 C 5.079400 -0.955100 -0.323100 N 4.743200 0.308600 0.057500 C 3.408300 0.768300 0.147600 N 1.741900 -2.291200 -0.825800 H 4.357400 -2.872500 -0.937000 H 6.139000 -1.186600 -0.358500 H 0.771400 -1.989900 -0.781800 H -3.185800 0.008600 4.198500 C -0.660500 -0.189900 4.012900 H -1.189100 -1.086800 4.361800 H 0.421100 -0.336700 4.067600 H 1.950700 -3.213400 -1.183200 H -4.429600 2.012200 -1.303300 H 5.455900 0.994400 0.290900 H -5.898200 1.491200 1.178800 C–Ag–2b (gas phase), -4463.7717 N -3.607000 2.079400 -0.205600 C -2.606100 -1.307000 0.157200 C -3.856900 -1.933800 0.240800 C -5.045100 -1.172200 0.159300 N -5.098600 0.160800 0.006300 C -3.893700 0.724000 -0.064200 C -2.634000 0.092800 -0.001500 N -1.628600 1.055300 -0.100000 C -2.254500 2.225300 -0.220500 O -1.389700 -1.928100 0.222300 H -6.002000 -1.685000 0.224100 H -1.763500 3.182900 -0.317700 H -1.914300 -3.511300 1.503300 AG 0.434400 0.592500 -0.079400 O 3.136300 1.946100 0.435900 N 2.436100 -0.167800 -0.171300 C 2.774200 -1.428800 -0.507000 C 4.143900 -1.846800 -0.577400 C 5.101200 -0.920700 -0.282600 N 4.747600 0.348300 0.062400 C 3.407100 0.793800 0.132300 N 1.783000 -2.310600 -0.770200 H 4.406600 -2.862500 -0.849600 H 6.163800 -1.140200 -0.305200 H 0.810900 -2.014300 -0.750000 H -3.935000 -3.007700 0.368100 C -1.394600 -3.346700 0.552000 H -1.879200 -3.921300 -0.247100 H -0.342800 -3.626800 0.646500 H 2.004700 -3.235400 -1.112900 H -4.296900 2.820000 -0.276700 H 5.450700 1.048500 0.282300 C–Ag–2b (COSMO), -4522.3060 N -3.635900 2.052500 -0.224100 C -2.590800 -1.315100 0.177400 C -3.833800 -1.966800 0.242600 C -5.029600 -1.229000 0.142400

  15

N -5.108200 0.109200 -0.016800 C -3.906700 0.700800 -0.073800 C -2.640900 0.083000 0.012400 N -1.646000 1.054600 -0.083900 C -2.286700 2.214000 -0.224800 O -1.373200 -1.911800 0.265600 H -5.976300 -1.760600 0.196000 H -1.811500 3.177000 -0.327800 H -1.875800 -3.589500 1.430400 AG 0.434700 0.632700 -0.078500 O 3.240900 1.956700 0.411000 N 2.446000 -0.131100 -0.165400 C 2.730400 -1.420700 -0.486200 C 4.079900 -1.895100 -0.549400 C 5.073500 -1.006000 -0.273400 N 4.767200 0.284000 0.048600 C 3.458500 0.768100 0.114400 N 1.712900 -2.258400 -0.743300 H 4.290400 -2.926400 -0.805900 H 6.126500 -1.258400 -0.290600 H 0.750600 -1.934800 -0.717700 H -3.891900 -3.041200 0.370800 C -1.353600 -3.355000 0.496700 H -1.825500 -3.873800 -0.344800 H -0.298100 -3.619400 0.573900 H 1.900800 -3.209400 -1.032300 H -4.320600 2.795100 -0.315400 H 5.508300 0.947400 0.253400 C–Ag–2b (tilted), -4462.6661 N -3.698100 1.652100 -0.678700 C -2.224800 0.489600 2.334500 C -3.341100 0.496400 3.181900 C -4.606300 0.896700 2.694600 N -4.858200 1.296000 1.437500 C -3.775700 1.282500 0.661700 C -2.461500 0.906600 1.009500 N -1.628600 1.055300 -0.100000 C -2.408200 1.501700 -1.083900 O -0.953400 0.126200 2.682600 H -5.455900 0.889400 3.373500 H -2.073200 1.723800 -2.086900 H -0.994100 0.732800 4.695800 AG 0.434400 0.592500 -0.079400 O 3.136300 1.946100 0.435900 N 2.436100 -0.167800 -0.171300 C 2.774200 -1.428800 -0.507000 C 4.143900 -1.846800 -0.577400 C 5.101200 -0.920700 -0.282600 N 4.747600 0.348300 0.062400 C 3.407100 0.793800 0.132300 N 1.783000 -2.310600 -0.770200 H 4.406600 -2.862500 -0.849600 H 6.163800 -1.140200 -0.305200 H 0.810900 -2.014300 -0.750000 H -3.254800 0.195800 4.220100 C -0.710300 -0.138600 4.093900 H -1.275200 -1.021300 4.418200 H 0.364700 -0.316000 4.175400 H 2.004700 -3.235400 -1.112900 H -4.475300 1.981700 -1.241500

  16

H 5.450700 1.048500 0.282300 C–Ag–3a (gas phase), -4066.6228 N -3.398256 -0.156970 -0.010584 C -4.282449 -1.241082 -0.036664 N -5.655136 -0.908273 -0.045981 C -6.118077 0.373438 -0.030078 C -5.245595 1.420758 -0.004218 C -3.843492 1.117273 0.005036 N -2.936998 2.115097 0.029891 O -3.911446 -2.406755 -0.050783 AG -1.350361 -0.774512 -0.000137 H -7.195666 0.500791 -0.039132 C 2.788347 1.979283 0.053083 C 4.052818 1.341934 0.056224 C 4.182065 -0.047188 0.045643 C 2.992757 -0.785972 0.031554 C 1.713887 -0.180953 0.027924 C 1.635901 1.215567 0.039092 N 2.726403 -2.155043 0.018340 C 1.376968 -2.330347 0.007632 N 0.728106 -1.169334 0.012887 F 0.398951 1.820686 0.035886 H 4.945554 1.959636 0.067267 H 0.907628 -3.303858 -0.003707 H 5.156974 -0.525960 0.048225 H 2.709646 3.062259 0.061521 H -3.235541 3.081009 0.041721 H -1.941828 1.914863 0.035641 H -5.595083 2.446624 0.008672 H -6.294476 -1.697893 -0.065260 H 3.412295 -2.901148 0.016801 C–Ag–3a (COSMO), -4122.1386 N -3.417200 -0.203600 -0.006600 C -4.337000 -1.233300 -0.087400 N -5.686500 -0.874200 -0.091800 C -6.118000 0.418500 -0.019700 C -5.216600 1.435500 0.060000 C -3.826100 1.091000 0.064500 N -2.897800 2.056000 0.138800 O -4.003600 -2.430400 -0.153800 AG -1.350900 -0.793100 0.001900 H -7.190600 0.566900 -0.031700 C 2.804100 1.999000 -0.010700 C 4.068300 1.359600 0.027700 C 4.191900 -0.031200 0.063800 C 3.000300 -0.768100 0.060400 C 1.720800 -0.160400 0.022700 C 1.648900 1.235600 -0.012500 N 2.736600 -2.131600 0.089600 C 1.392300 -2.308400 0.070600 N 0.737000 -1.148600 0.029900 F 0.416900 1.848900 -0.051500 H 4.962400 1.975700 0.028400 H 0.927400 -3.282200 0.085100 H 5.161200 -0.519000 0.093200 H 2.726400 3.081600 -0.039000 H -3.174500 3.027700 0.193800 H -1.907600 1.833800 0.142300 H -5.527400 2.471600 0.117400

  17

H -6.358400 -1.633200 -0.151600 H 3.422600 -2.877100 0.118500 C–Ag–3a (tilted), -4064.2285 N -3.398300 -0.157000 -0.010600 C -4.282400 -1.241100 -0.036700 N -5.655100 -0.908300 -0.046000 C -6.118100 0.373400 -0.030100 C -5.245600 1.420800 -0.004200 C -3.843500 1.117300 0.005000 N -2.937000 2.115100 0.029900 O -3.911400 -2.406800 -0.050800 AG -1.350400 -0.774500 -0.000100 H -7.195700 0.500800 -0.039100 C 1.717200 -1.638200 -3.815800 C 3.049900 -2.045300 -3.563800 C 3.540400 -2.214300 -2.268700 C 2.645000 -1.960300 -1.222600 C 1.307800 -1.552500 -1.439500 C 0.862500 -1.396600 -2.756200 N 2.766500 -2.019400 0.165600 C 1.573200 -1.667600 0.716900 N 0.666200 -1.378500 -0.211900 F -0.436300 -1.000100 -2.985100 H 3.705000 -2.229900 -4.409600 H 1.402300 -1.633200 1.783600 H 4.564500 -2.526900 -2.086600 H 1.355100 -1.512400 -4.831700 H -3.235500 3.081000 0.041700 H -1.941800 1.914900 0.035600 H -5.595100 2.446600 0.008700 H -6.294500 -1.697900 -0.065300 H 3.596600 -2.278700 0.686100 C–Ag–3b (gas phase), -3959.8629 N -3.396093 -0.146427 -0.014173 C -4.274361 -1.234501 -0.076640 N -5.648295 -0.909062 -0.086522 C -6.118279 0.369218 -0.039098 C -5.251793 1.420361 0.021668 C -3.848404 1.124453 0.033060 N -2.947025 2.125938 0.092044 O -3.895139 -2.396708 -0.120351 AG -1.348607 -0.765375 -0.002414 H -7.196528 0.491036 -0.052545 C 2.853644 1.934002 0.171610 C 4.072380 1.211457 0.170077 N 4.167185 -0.128782 0.125276 C 2.991688 -0.747519 0.080771 C 1.703411 -0.161385 0.075836 C 1.659884 1.232084 0.123831 N 2.750253 -2.118398 0.028605 C 1.403615 -2.309682 -0.004767 N 0.732915 -1.157529 0.022013 F 0.455428 1.881154 0.123225 H 5.011132 1.758593 0.207362 H 0.946654 -3.288205 -0.048020 H 2.851639 3.019179 0.209529 H -3.250018 3.089946 0.128256 H -1.951304 1.929319 0.099494 H -5.607502 2.443453 0.060024

  18

H -6.283379 -1.701198 -0.132106 H 3.463337 -2.840957 0.017049 C–Ag–3b (COSMO), -4018.9044 N -3.414100 -0.194400 -0.014700 C -4.332900 -1.221900 -0.128700 N -5.682500 -0.863400 -0.134400 C -6.115300 0.426700 -0.031400 C -5.215100 1.441800 0.080500 C -3.824400 1.097900 0.084900 N -2.897000 2.060900 0.189200 O -3.998200 -2.416800 -0.223000 AG -1.347200 -0.788700 0.003100 H -7.187900 0.575000 -0.047200 C 2.856500 1.959700 0.109600 C 4.074800 1.247200 0.137500 N 4.179400 -0.099100 0.135400 C 3.002600 -0.731500 0.103000 C 1.713100 -0.143300 0.071800 C 1.664800 1.248800 0.077100 N 2.764300 -2.096800 0.094600 C 1.420300 -2.290200 0.059200 N 0.745500 -1.140500 0.044200 F 0.465600 1.896800 0.050200 H 5.008500 1.802300 0.162700 H 0.970300 -3.270700 0.043600 H 2.848500 3.044700 0.113600 H -3.173800 3.031400 0.261500 H -1.907000 1.838500 0.188500 H -5.527400 2.475800 0.162500 H -6.353400 -1.620900 -0.219700 H 3.466200 -2.829000 0.109000 C–Ag–3b (tilted), -3957.9599 N -3.393100 -0.175300 0.031300 C -3.894200 0.032500 -1.259000 N -5.248100 0.427000 -1.331000 C -6.039300 0.601600 -0.235200 C -5.538700 0.395600 1.016300 C -4.166000 -0.005700 1.124800 N -3.619300 -0.222900 2.338500 O -3.219100 -0.113000 -2.268700 AG -1.338700 -0.770400 0.009800 H -7.064300 0.906500 -0.419900 C 2.834200 1.978300 0.095100 C 4.061100 1.269900 0.075600 N 4.170700 -0.069300 0.036100 C 3.001900 -0.701900 0.015800 C 1.707000 -0.130700 0.030700 C 1.648100 1.262400 0.072200 N 2.775600 -2.075700 -0.025000 C 1.430900 -2.282800 -0.033400 N 0.747400 -1.138300 -0.000700 F 0.436300 1.897400 0.089600 H 4.993900 1.828100 0.093400 H 0.984700 -3.266700 -0.063500 H 2.820200 3.063600 0.127400 H -4.168600 -0.105100 3.179200 H -2.648800 -0.506000 2.428300 H -6.153200 0.529600 1.899000 H -5.608900 0.577300 -2.269100

  19

H 3.496800 -2.790000 -0.045500 C–Ag–4a (gas phase), -4022.6189 N -3.440199 -0.170540 0.043952 C -4.231476 -1.262344 -0.330606 N -5.624084 -1.025704 -0.358723 C -6.189902 0.173142 -0.043608 C -5.408003 1.227607 0.324600 C -3.989120 1.020245 0.361969 N -3.169101 2.029440 0.720994 O -3.769160 -2.357910 -0.617903 AG -1.348535 -0.643598 0.028071 H -7.271910 0.230484 -0.103260 C 3.102194 1.827583 -0.154424 C 4.289781 1.080274 0.010747 C 4.268992 -0.301369 0.190855 C 3.009679 -0.907925 0.203614 C 1.798265 -0.188156 0.045825 C 1.858165 1.203668 -0.139602 N 2.617795 -2.236224 0.354442 C 1.261725 -2.288829 0.290828 N 0.727184 -1.084367 0.107950 CL 0.394202 2.164665 -0.382255 H 5.240425 1.604063 -0.007656 H 0.700596 -3.208152 0.380040 H 5.183627 -0.874390 0.313414 H 3.156596 2.901824 -0.299993 H -3.544645 2.932575 0.976882 H -2.163516 1.892325 0.752502 H -5.839374 2.188687 0.579182 H -6.194890 -1.820335 -0.633347 H 3.230510 -3.032861 0.484949 C–Ag–4a (COSMO), -4077.9405 N -3.447700 -0.213500 0.041600 C -4.284100 -1.240000 -0.359600 N -5.650600 -0.957000 -0.409300 C -6.175600 0.261100 -0.089200 C -5.357200 1.273700 0.308100 C -3.951700 1.005300 0.369800 N -3.102600 1.969900 0.754500 O -3.864200 -2.370300 -0.666600 AG -1.348600 -0.685600 0.060800 H -7.251200 0.356000 -0.171900 C 3.091300 1.853400 -0.217000 C 4.286700 1.118100 -0.045500 C 4.274900 -0.260300 0.169300 C 3.020100 -0.876100 0.208700 C 1.800000 -0.168400 0.042800 C 1.851600 1.218500 -0.175100 N 2.644400 -2.198200 0.397700 C 1.293700 -2.265900 0.349200 N 0.739500 -1.071500 0.137600 CL 0.374400 2.167400 -0.411500 H 5.233400 1.647800 -0.085300 H 0.746400 -3.188100 0.469500 H 5.189700 -0.830000 0.299700 H 3.135900 2.924700 -0.385600 H -3.450800 2.882500 1.018700 H -2.105100 1.794900 0.820900 H -5.743100 2.251500 0.568800

  20

H -6.260300 -1.712900 -0.706100 H 3.265300 -2.985100 0.547800 C–Ag–4a (tilted), -4021.1505 N -3.440200 -0.170500 0.044000 C -3.999600 -0.206700 -1.238300 N -5.374800 0.108600 -1.313300 C -6.134000 0.426600 -0.227400 C -5.577800 0.453400 1.017100 C -4.182600 0.139100 1.127200 N -3.582100 0.149200 2.335100 O -3.359200 -0.490500 -2.241200 AG -1.348500 -0.643600 0.028100 H -7.179400 0.650100 -0.413900 C 3.102200 1.827600 -0.154400 C 4.289800 1.080300 0.010700 C 4.269000 -0.301400 0.190900 C 3.009700 -0.907900 0.203600 C 1.798300 -0.188200 0.045800 C 1.858200 1.203700 -0.139600 N 2.617800 -2.236200 0.354400 C 1.261700 -2.288800 0.290800 N 0.727200 -1.084400 0.108000 CL 0.394200 2.164700 -0.382300 H 5.240400 1.604100 -0.007700 H 0.700600 -3.208200 0.380000 H 5.183600 -0.874400 0.313400 H 3.156600 2.901800 -0.300000 H -4.108600 0.365500 3.170700 H -2.595500 -0.073700 2.424000 H -6.165300 0.703600 1.892800 H -5.776600 0.083400 -2.246400 H 3.230500 -3.032900 0.484900 C–Ag–4b (gas phase), -3915.9995 N -3.448594 -0.173264 0.042233 C -4.225933 -1.275619 -0.332660 N -5.620041 -1.053181 -0.374588 C -6.200526 0.141678 -0.071697 C -5.432494 1.206524 0.296568 C -4.012316 1.013913 0.347523 N -3.204775 2.033739 0.705534 O -3.748861 -2.367663 -0.608717 AG -1.355066 -0.638449 0.045280 H -7.282551 0.187586 -0.140699 C 3.137438 1.786456 -0.166642 C 4.276933 0.963957 -0.014320 N 4.236698 -0.367882 0.156872 C 3.005670 -0.864780 0.176153 C 1.779117 -0.165159 0.041409 C 1.863439 1.221278 -0.141137 N 2.641639 -2.198612 0.332156 C 1.285647 -2.269642 0.292423 N 0.724417 -1.071960 0.120466 CL 0.430674 2.221123 -0.354889 H 5.264608 1.417917 -0.036229 H 0.738876 -3.196723 0.389776 H 3.259558 2.855584 -0.307199 H -3.590806 2.932940 0.960015 H -2.199552 1.902058 0.754127 H -5.876068 2.164587 0.541440

  21

H -6.180676 -1.855246 -0.648986 H 3.286743 -2.973514 0.450424 C–Ag–4b (COSMO), -3974.2761 N -3.454900 -0.216200 0.032300 C -4.285300 -1.262000 -0.329800 N -5.654500 -0.992200 -0.379000 C -6.188200 0.230200 -0.091500 C -5.375900 1.261700 0.268000 C -3.967600 1.007400 0.327700 N -3.124700 1.989800 0.678700 O -3.857500 -2.397800 -0.603900 AG -1.352700 -0.679400 0.057500 H -7.265300 0.313000 -0.168000 C 3.119100 1.820200 -0.177500 C 4.266800 1.016300 -0.029100 N 4.246400 -0.320700 0.147700 C 3.018100 -0.840600 0.174500 C 1.783800 -0.148800 0.040100 C 1.852200 1.235800 -0.145000 N 2.668300 -2.169900 0.337900 C 1.315700 -2.253300 0.303800 N 0.739500 -1.063300 0.126300 CL 0.408500 2.221300 -0.345900 H 5.246300 1.485600 -0.057600 H 0.783600 -3.185900 0.409000 H 3.227200 2.890100 -0.318800 H -3.478500 2.907200 0.917300 H -2.125800 1.823800 0.744800 H -5.768600 2.243300 0.502800 H -6.259800 -1.763000 -0.645100 H 3.307200 -2.948300 0.461200 C–Ag–4b (tilted), -3915.0212 N -3.448600 -0.173300 0.042200 C -4.007800 -0.299800 -1.235000 N -5.384200 0.001900 -1.331000 C -6.145400 0.388500 -0.269200 C -5.589700 0.503500 0.970700 C -4.193000 0.205700 1.101800 N -3.591600 0.303100 2.305600 O -3.364400 -0.647900 -2.215400 AG -1.355100 -0.638400 0.045300 H -7.192100 0.592300 -0.470300 C 3.137400 1.786500 -0.166600 C 4.276900 0.964000 -0.014300 N 4.236700 -0.367900 0.156900 C 3.005700 -0.864800 0.176200 C 1.779100 -0.165200 0.041400 C 1.863400 1.221300 -0.141100 N 2.641600 -2.198600 0.332200 C 1.285600 -2.269600 0.292400 N 0.724400 -1.072000 0.120500 CL 0.430700 2.221100 -0.354900 H 5.264600 1.417900 -0.036200 H 0.738900 -3.196700 0.389800 H 3.259600 2.855600 -0.307200 H -4.120000 0.565500 3.126800 H -2.606000 0.083800 2.408200 H -6.179100 0.809400 1.827300 H -5.785900 -0.089400 -2.260100

  22

H 3.286700 -2.973500 0.450400 C–Ag–5a (gas phase), -4009.7280 N -3.424165 -0.169761 -0.094720 C -4.211646 -1.246146 0.328403 N -5.607417 -1.027748 0.305766 C -6.179624 0.139574 -0.102670 C -5.401278 1.178743 -0.518438 C -3.979182 0.990075 -0.503686 N -3.162646 1.985046 -0.906703 O -3.744143 -2.315217 0.696321 AG -1.326652 -0.618864 -0.011669 H -7.263486 0.185013 -0.075673 C 3.215515 1.750630 0.081325 C 4.375131 0.962325 -0.097222 C 4.305592 -0.421225 -0.244631 C 3.027911 -0.987192 -0.213908 C 1.841124 -0.226802 -0.044942 C 1.953068 1.165275 0.110553 N 2.595334 -2.306380 -0.326123 C 1.240488 -2.317478 -0.232741 N 0.744632 -1.094443 -0.065614 BR 0.401515 2.287754 0.411661 H 5.341738 1.456287 -0.113967 H 0.650771 -3.221293 -0.290109 H 5.197957 -1.026768 -0.375510 H 3.313334 2.824757 0.202392 H -3.542615 2.866900 -1.223116 H -2.153705 1.867712 -0.885555 H -5.837507 2.114808 -0.847202 H -6.175425 -1.811118 0.616116 H 3.182233 -3.123197 -0.450678 C–Ag–5a (COSMO), -4064.7638 N -3.424500 -0.206200 -0.083200 C -4.251200 -1.191100 0.427700 N -5.620500 -0.917900 0.445900 C -6.157500 0.251500 -0.007600 C -5.348400 1.224000 -0.510400 C -3.940200 0.964800 -0.540900 N -3.100000 1.891000 -1.027100 O -3.820500 -2.276900 0.856000 AG -1.322200 -0.668700 -0.070000 H -7.234400 0.342600 0.060000 C 3.203800 1.772000 0.212400 C 4.376500 0.997800 0.048400 C 4.320500 -0.379500 -0.164400 C 3.046900 -0.954600 -0.208800 C 1.846700 -0.209100 -0.049700 C 1.944900 1.176100 0.164500 N 2.634100 -2.265000 -0.400100 C 1.282400 -2.293200 -0.358000 N 0.761800 -1.083200 -0.149800 BR 0.367400 2.281500 0.410600 H 5.339400 1.497500 0.091300 H 0.708700 -3.198700 -0.481300 H 5.216500 -0.979400 -0.290400 H 3.287100 2.841200 0.378200 H -3.457600 2.764800 -1.390900 H -2.100500 1.720100 -1.072200 H -5.743700 2.163200 -0.877600

  23

H -6.223500 -1.644800 0.819000 H 3.233100 -3.069200 -0.547900 C–Ag–5a (tilted), -4008.0628 N -3.424200 -0.169800 -0.094700 C -4.017200 -0.181700 1.172600 N -5.399700 0.108300 1.202600 C -6.136000 0.378400 0.088300 C -5.547400 0.380900 -1.141400 C -4.143300 0.093800 -1.205500 N -3.511300 0.081300 -2.397000 O -3.399200 -0.426000 2.199800 AG -1.326700 -0.618900 -0.011700 H -7.190400 0.585000 0.240800 C 3.215500 1.750600 0.081300 C 4.375100 0.962300 -0.097200 C 4.305600 -0.421200 -0.244600 C 3.027900 -0.987200 -0.213900 C 1.841100 -0.226800 -0.044900 C 1.953100 1.165300 0.110600 N 2.595300 -2.306400 -0.326100 C 1.240500 -2.317500 -0.232700 N 0.744600 -1.094400 -0.065600 BR 0.401500 2.287800 0.411700 H 5.341700 1.456300 -0.114000 H 0.650800 -3.221300 -0.290100 H 5.198000 -1.026800 -0.375500 H 3.313300 2.824800 0.202400 H -4.018200 0.270600 -3.250900 H -2.514100 -0.105400 -2.452400 H -6.116100 0.593000 -2.039200 H -5.825800 0.100900 2.125100 H 3.182200 -3.123200 -0.450700 C–Ag–5b (gas phase), -3903.2117 N -3.453446 -0.194896 0.055229 C -4.220925 -1.292733 -0.351109 N -5.618539 -1.088825 -0.365328 C -6.211166 0.084400 -0.006298 C -5.452584 1.144807 0.392787 C -4.029016 0.971274 0.414673 N -3.230789 1.987663 0.801453 O -3.733374 -2.366971 -0.674972 AG -1.352871 -0.635373 0.029032 H -7.294653 0.117135 -0.057594 C 3.209252 1.714781 -0.134770 C 4.325147 0.867456 0.059439 N 4.248275 -0.460693 0.241195 C 3.006225 -0.928977 0.230449 C 1.797938 -0.202859 0.054991 C 1.922930 1.178322 -0.140706 N 2.610456 -2.253172 0.388337 C 1.255189 -2.295930 0.313143 N 0.723970 -1.088809 0.115234 BR 0.394211 2.318580 -0.449139 H 5.323208 1.298977 0.062066 H 0.686125 -3.210042 0.404926 H 3.366535 2.778236 -0.282781 H -3.625810 2.872409 1.090378 H -2.221560 1.875470 0.814205 H -5.905656 2.085848 0.682226

  24

H -6.171957 -1.887666 -0.662726 H 3.236131 -3.039987 0.530131 C–Ag–5b (COSMO), -3961.1481 N -3.458300 -0.233700 0.046200 C -4.268500 -1.262100 -0.402300 N -5.642500 -1.014500 -0.433000 C -6.199100 0.171600 -0.052600 C -5.406300 1.187100 0.387300 C -3.993900 0.954300 0.431300 N -3.169200 1.923500 0.856100 O -3.819500 -2.364100 -0.764900 AG -1.348600 -0.670700 0.061300 H -7.277500 0.240000 -0.124500 C 3.200000 1.738100 -0.202200 C 4.324100 0.908500 -0.011300 N 4.264600 -0.420800 0.205900 C 3.022900 -0.907200 0.229800 C 1.807300 -0.187800 0.056200 C 1.918000 1.187800 -0.170400 N 2.638400 -2.222000 0.427500 C 1.285200 -2.273400 0.375900 N 0.740800 -1.075900 0.154600 BR 0.373400 2.310900 -0.449200 H 5.316100 1.351000 -0.038900 H 0.728600 -3.188900 0.501500 H 3.343900 2.799000 -0.374400 H -3.541900 2.810600 1.169300 H -2.168600 1.767300 0.920900 H -5.817400 2.140000 0.697100 H -6.233200 -1.772500 -0.761400 H 3.256200 -3.011500 0.584300 C–Ag–5b (tilted), -3902.0176 N -3.453400 -0.194900 0.055200 C -4.016100 -0.264000 -1.224600 N -5.398800 0.014700 -1.299500 C -6.163100 0.326200 -0.215400 C -5.604000 0.385100 1.026900 C -4.200400 0.110900 1.136400 N -3.595900 0.155000 2.341600 O -3.371000 -0.546900 -2.224900 AG -1.352900 -0.635400 0.029000 H -7.214800 0.518400 -0.401300 C 3.209300 1.714800 -0.134800 C 4.325100 0.867500 0.059400 N 4.248300 -0.460700 0.241200 C 3.006200 -0.929000 0.230400 C 1.797900 -0.202900 0.055000 C 1.922900 1.178300 -0.140700 N 2.610500 -2.253200 0.388300 C 1.255200 -2.295900 0.313100 N 0.724000 -1.088800 0.115200 BR 0.394200 2.318600 -0.449100 H 5.323200 1.299000 0.062100 H 0.686100 -3.210000 0.404900 H 3.366500 2.778200 -0.282800 H -4.125000 0.367700 3.176500 H -2.601400 -0.031900 2.427500 H -6.195500 0.631100 1.901100 H -5.803000 -0.034700 -2.230700

  25

H 3.236100 -3.040000 0.530100 C*–Ag–A (gas phase), -4127.4429 N -3.283165 -0.482832 -0.014212 C -4.342478 -1.321501 -0.023632 C -5.688589 -0.829318 -0.030124 C -5.866374 0.522175 -0.026555 N -4.787863 1.356801 -0.016777 C -3.458300 0.901591 -0.009832 O -2.520677 1.697077 -0.000569 N -4.105924 -2.647596 -0.026812 AG -1.196353 -0.964129 -0.003666 H -6.532652 -1.509249 -0.037618 H -6.844015 0.992832 -0.031055 N 2.838514 2.061732 0.066379 C 4.022074 1.426616 0.069896 N 4.255967 0.099715 0.055484 C 3.113478 -0.588015 0.036407 C 1.806665 -0.073135 0.030677 C 1.690504 1.345661 0.046453 N 2.966111 -1.970417 0.018194 C 1.635505 -2.252911 0.002776 N 0.897219 -1.142652 0.009623 N 0.526847 2.034056 0.043505 H 4.901107 2.066852 0.086352 H 3.728328 -2.640224 0.016851 H 1.245983 -3.259923 -0.012994 H -0.398661 1.619802 0.025651 H 0.591905 3.045819 0.055094 H -4.868556 -3.312047 -0.033322 H -3.154453 -2.997783 -0.021779 H -4.905564 2.366619 -0.013818 C*–Ag–A (COSMO), -4191.2235 N -3.282200 -0.442400 -0.013900 C -4.316400 -1.323100 -0.034400 C -5.676400 -0.874000 -0.039100 C -5.896100 0.469500 -0.021800 N -4.841600 1.336300 -0.000100 C -3.511300 0.920900 0.005100 O -2.588400 1.759500 0.025100 N -4.038400 -2.633700 -0.050200 AG -1.200600 -0.946300 -0.005200 H -6.492500 -1.586200 -0.055300 H -6.882600 0.916300 -0.022300 N 2.866100 2.051200 0.049500 C 4.047800 1.404600 0.061100 N 4.277900 0.078600 0.060100 C 3.125900 -0.619200 0.044400 C 1.828500 -0.086500 0.030500 C 1.711400 1.327900 0.034100 N 2.962600 -1.990400 0.037000 C 1.626600 -2.252200 0.018200 N 0.904400 -1.134200 0.013700 N 0.542100 1.999300 0.022100 H 4.929700 2.041200 0.072400 H 3.701300 -2.685500 0.041800 H 1.224600 -3.253200 0.006800 H -0.368000 1.547000 0.019500 H 0.567400 3.012500 0.031600 H -4.784300 -3.317200 -0.065100

  26

H -3.079000 -2.962500 -0.040400 H -5.005500 2.338300 0.013300 C*–Ag–6a (gas phase), -4331.6586 N -3.269314 -0.452544 -0.036400 C -4.271653 -1.239876 -0.479749 C -5.631974 -0.787525 -0.499266 C -5.881468 0.477471 -0.056567 N -4.859480 1.265510 0.382259 C -3.513467 0.848852 0.410922 O -2.630371 1.602074 0.809051 N -3.965315 -2.481285 -0.907586 AG -1.181286 -0.915874 0.081590 H -6.430197 -1.429073 -0.854032 H -6.875240 0.912385 -0.031718 C 2.811432 2.001201 -0.507113 C 4.097861 1.432883 -0.426186 C 4.299150 0.095363 -0.081410 C 3.136557 -0.646739 0.150689 C 1.835159 -0.103965 0.053114 C 1.642032 1.263711 -0.258645 N 2.941904 -1.991198 0.470946 C 1.606032 -2.229384 0.539143 N 0.901637 -1.127777 0.291360 N 0.366805 1.821727 -0.385681 H 4.958505 2.064662 -0.624908 H 3.667955 -2.679873 0.626628 H 1.190189 -3.200332 0.764823 H -0.321939 1.599326 0.330518 H 0.370565 2.819060 -0.578693 H -4.680989 -3.098416 -1.267559 H -2.999567 -2.790934 -0.922641 H -5.030357 2.211005 0.713603 H 2.712213 3.055206 -0.758201 H 5.291062 -0.339199 -0.003810 C*–Ag–6a (COSMO), -4389.1784 N -3.294100 -0.438100 -0.007300 C -4.291700 -1.331500 -0.234200 C -5.666800 -0.931100 -0.226400 C -5.938900 0.381000 0.014400 N -4.921100 1.263000 0.236700 C -3.575500 0.895000 0.234500 O -2.687800 1.743700 0.442200 N -3.962800 -2.610000 -0.466200 AG -1.200500 -0.886500 0.017900 H -6.452900 -1.654300 -0.406500 H -6.941100 0.790200 0.043500 C 2.945200 2.035100 -0.197500 C 4.208300 1.415700 -0.093400 C 4.346700 0.034400 0.070300 C 3.149000 -0.691500 0.118900 C 1.869700 -0.094400 0.011400 C 1.739800 1.307600 -0.150100 N 2.902000 -2.051900 0.261800 C 1.561500 -2.249200 0.236600 N 0.897200 -1.104300 0.087000 N 0.506900 1.937700 -0.329100 H 5.097700 2.038300 -0.137400 H 3.597500 -2.781500 0.363800 H 1.107900 -3.224200 0.326400

  27

H -0.305500 1.528200 0.129100 H 0.534900 2.945600 -0.200500 H -4.679500 -3.300300 -0.649200 H -2.991600 -2.901800 -0.485800 H -5.124900 2.241300 0.417000 H 2.885900 3.114500 -0.320300 H 5.314600 -0.449600 0.154300 C*–Ag–6b (gas phase), -4229.3068 N -3.287077 -0.475843 -0.000739 C -4.324248 -1.318748 0.194590 C -5.681309 -0.857470 0.174380 C -5.892574 0.470933 -0.046428 N -4.836163 1.311979 -0.236297 C -3.494909 0.887509 -0.218858 O -2.579068 1.688977 -0.388652 N -4.055317 -2.621534 0.409187 AG -1.194919 -0.933746 -0.037752 H -6.507228 -1.541948 0.329483 H -6.880846 0.917546 -0.080720 C 2.897341 2.030069 0.339605 C 4.130781 1.367901 0.272520 N 4.287507 0.040201 0.084066 C 3.123759 -0.593132 -0.024120 C 1.817527 -0.059126 0.030675 C 1.670180 1.339178 0.213020 N 2.949066 -1.963927 -0.211775 C 1.618188 -2.222068 -0.256003 N 0.895843 -1.108779 -0.112733 N 0.464676 1.983673 0.311397 H 5.047275 1.945108 0.370720 H 3.701519 -2.638847 -0.296694 H 1.211771 -3.213376 -0.390268 H -0.394921 1.592026 -0.059225 H 0.481776 2.996277 0.331689 H 2.881943 3.107599 0.486866 H -4.799963 -3.285782 0.574275 H -3.095220 -2.945703 0.446947 H -4.978846 2.305019 -0.399926 C*–Ag–6b (COSMO), -4290.1189 N -3.294100 -0.443900 -0.018000 C -4.310400 -1.342200 0.058500 C -5.679500 -0.922000 0.038600 C -5.927000 0.413100 -0.060300 N -4.890800 1.298600 -0.135100 C -3.551400 0.911700 -0.114500 O -2.646400 1.766200 -0.181500 N -4.005900 -2.643700 0.154200 AG -1.203500 -0.914700 -0.007800 H -6.480500 -1.648600 0.100100 H -6.922700 0.838400 -0.083500 C 2.947700 2.033200 0.169100 C 4.170600 1.357000 0.115400 N 4.317000 0.010600 0.029600 C 3.138600 -0.628500 -0.000500 C 1.842900 -0.068500 0.046000 C 1.711100 1.339300 0.138600 N 2.938900 -1.999200 -0.086300 C 1.601600 -2.232900 -0.091200 N 0.901100 -1.102500 -0.012000

  28

N 0.518800 1.997000 0.233000 H 5.092100 1.934100 0.140600 H 3.662800 -2.707200 -0.140800 H 1.177700 -3.222900 -0.152800 H -0.366000 1.547000 0.016400 H 0.527500 3.006500 0.146000 H 2.939200 3.118200 0.236800 H -4.737700 -3.339700 0.216400 H -3.040000 -2.952300 0.173800 H -5.075600 2.294400 -0.208100 C*–Ag–1a (gas phase), -4208.3288 N -3.208613 -0.436698 -0.008634 C -4.315000 -1.120416 0.354302 C -5.618530 -0.527786 0.290438 C -5.703782 0.760366 -0.147262 N -4.577048 1.440535 -0.504343 C -3.287584 0.884267 -0.447557 O -2.306256 1.550638 -0.777369 N -4.165377 -2.389884 0.779792 AG -1.167101 -1.088958 -0.006748 H -6.501913 -1.084493 0.580995 H -6.642104 1.298560 -0.231038 C 2.507281 2.084572 0.569035 C 3.843013 1.679175 0.353204 C 4.168845 0.378453 -0.031423 C 3.092940 -0.502971 -0.178897 C 1.748437 -0.121635 0.038325 C 1.435637 1.205851 0.408835 N 3.031705 -1.857694 -0.510701 C 1.730494 -2.249358 -0.481386 N 0.925542 -1.242839 -0.154167 O 0.158107 1.628323 0.715573 H 4.637615 2.407043 0.487668 H 3.817948 -2.457141 -0.731323 H 1.413269 -3.258661 -0.699737 H -0.484690 1.528255 -0.021639 H -4.962348 -2.936311 1.078417 H -3.239530 -2.798659 0.848155 H -4.624258 2.403804 -0.825880 H 2.286457 3.104969 0.868939 H 5.196314 0.069379 -0.199887 C*–Ag–1a (COSMO), -4268.0872 N -3.274100 -0.445400 -0.014700 C -4.320100 -1.311700 -0.021200 C -5.673200 -0.842700 -0.005000 C -5.872600 0.503800 0.022900 N -4.805500 1.355700 0.032600 C -3.482400 0.920500 0.011600 O -2.545100 1.743600 0.017600 N -4.059100 -2.625600 -0.044000 AG -1.199400 -0.964100 -0.024600 H -6.499900 -1.542500 -0.012300 H -6.852300 0.964800 0.039900 C 2.826900 2.092700 0.063600 C 4.114000 1.512200 0.085700 C 4.301000 0.127900 0.080900 C 3.135100 -0.646600 0.051300 C 1.830300 -0.092600 0.027600 C 1.666500 1.310700 0.035000

  29

N 2.940200 -2.022400 0.037100 C 1.608200 -2.266700 0.005700 N 0.899000 -1.139200 -0.001000 O 0.456200 1.965500 0.013700 H 4.979800 2.167500 0.107400 H 3.663900 -2.731600 0.043200 H 1.191400 -3.261900 -0.012400 H -0.313600 1.356300 0.005000 H -4.813800 -3.299700 -0.044100 H -3.103800 -2.966300 -0.046300 H -4.954900 2.360000 0.054500 H 2.716700 3.173900 0.068500 H 5.287100 -0.325400 0.098700 C*–Ag–1b (gas phase), -4104.8658 N -3.270366 -0.501064 -0.014152 C -4.367281 -1.289161 -0.019588 C -5.687904 -0.732237 -0.026176 C -5.799841 0.626552 -0.026864 N -4.682368 1.408919 -0.021225 C -3.378873 0.888307 -0.014219 O -2.402345 1.637903 -0.008636 N -4.190699 -2.624140 -0.018792 AG -1.198219 -1.033824 -0.004252 H -6.564230 -1.370104 -0.030322 H -6.753541 1.143917 -0.031735 C 2.777248 2.109121 0.071664 C 4.036977 1.490019 0.073905 N 4.237067 0.156252 0.055576 C 3.101635 -0.530463 0.035208 C 1.770486 -0.045603 0.030640 C 1.590007 1.358083 0.049291 N 2.983322 -1.919680 0.013918 C 1.665530 -2.234787 -0.001565 N 0.895837 -1.144650 0.007692 O 0.422059 2.041538 0.049186 H 4.932661 2.106163 0.091179 H 3.763047 -2.568833 0.011014 H 1.300410 -3.250956 -0.019096 H -0.400540 1.507734 0.024148 H -4.981893 -3.254349 -0.022314 H -3.255502 -3.015690 -0.013220 H -4.750442 2.423492 -0.021365 H 2.701241 3.192450 0.086990 C*–Ag–1b (COSMO), -4167.0614 N -3.258000 -0.452700 -0.016000 C -4.339200 -1.274600 -0.041400 C -5.671200 -0.748700 -0.045000 C -5.813500 0.605100 -0.021600 N -4.711200 1.411100 0.004700 C -3.409700 0.918800 0.006900 O -2.438400 1.704500 0.028600 N -4.131300 -2.597400 -0.062600 AG -1.200000 -1.036100 -0.001300 H -6.527000 -1.412500 -0.066300 H -6.772600 1.107800 -0.021100 C 2.763800 2.104000 0.044400 C 4.028600 1.497700 0.055200 N 4.245100 0.161800 0.055100 C 3.112200 -0.548900 0.042400

  30

C 1.780200 -0.064700 0.029800 C 1.588900 1.332400 0.031800 N 2.994000 -1.930500 0.038200 C 1.673800 -2.242000 0.022300 N 0.905500 -1.154300 0.017000 O 0.399700 1.989900 0.022600 H 4.915500 2.125900 0.064300 H 3.758700 -2.596800 0.042000 H 1.309700 -3.257500 0.013500 H -0.399600 1.412200 0.019600 H -4.912100 -3.240800 -0.082400 H -3.190200 -2.975200 -0.062700 H -4.818300 2.420800 0.021200 H 2.682200 3.187000 0.045700

  31

Table S2. Cartesian coordinates (a.u.) and total bonding energies (kcal mol–1) of the geometry-optimized structures of the isolated nucleobases. Cytosine (gas phase), -1894.5624 N 0.004808 -0.261151 0.002130 C -0.014578 2.421139 -0.023002 N -1.191266 1.811715 0.034079 C -1.261595 0.435989 0.042279 C 1.207105 0.371869 -0.051436 C 1.255125 1.735257 -0.069063 N -0.023297 3.790587 -0.064117 H 2.093555 -0.254679 -0.079548 H 2.198081 2.269354 -0.120123 O -2.288457 -0.232036 0.085384 H 0.829366 4.309688 0.091356 H -0.909741 4.254401 0.097530 H -0.056794 -1.274110 0.015373 Cytosine (COSMO), -1913.9458 N -0.004937 -0.259497 0.001414 C -0.009144 2.433351 -0.025259 N -1.196553 1.797864 0.027012 C -1.231944 0.432527 0.041397 C 1.201026 0.376604 -0.052132 C 1.248965 1.738337 -0.067631 N -0.020473 3.783709 -0.037690 H 2.079597 -0.256616 -0.081005 H 2.189527 2.275625 -0.110025 O -2.295634 -0.229938 0.087987 H 0.842685 4.309205 -0.078925 H -0.900307 4.285103 -0.010144 H -0.045554 -1.274175 0.012898 Guanine (gas phase), -2448.3059 N 2.832033 1.692773 0.077712 C 3.900445 0.826043 0.041950 N 3.771067 -0.484391 0.006683 C 2.469746 -0.883285 0.021416 C 1.300892 -0.106895 0.043856 C 1.421151 1.330376 0.080291 N 2.028941 -2.186310 -0.001312 C 0.637398 -2.139987 0.008733 N 0.170655 -0.912148 0.035755 O 0.577561 2.215850 0.115894 N 5.165184 1.388623 0.097108 H 2.622980 -3.006573 -0.020628 H 0.043050 -3.044186 -0.006443 H 2.994231 2.693280 0.162866 H 5.908032 0.729758 -0.114169 H 5.283288 2.300999 -0.330024 Guanine (COSMO), -2471.3728 N 2.826841 1.693770 0.083591 C 3.904328 0.830101 0.053289 N 3.770011 -0.492596 0.023342 C 2.474021 -0.892918 0.019874 C 1.315278 -0.100021 0.047629 C 1.456393 1.321658 0.082336 N 2.016392 -2.187659 -0.005202 C 0.635769 -2.135131 0.007371 N 0.172185 -0.897535 0.038896

  32

O 0.572426 2.201548 0.110628 N 5.142808 1.393826 0.007741 H 2.587417 -3.025643 -0.029434 H 0.037912 -3.035551 -0.007816 H 3.007060 2.695154 0.102267 H 5.928829 0.779602 0.189105 H 5.254040 2.360791 0.290300 Adenine (gas phase), -2293.3390 N 2.874469 1.760380 0.053171 C 3.868469 0.846141 0.043743 N 3.778663 -0.496084 0.029267 C 2.496379 -0.896950 0.023323 C 1.357137 -0.074301 0.033585 C 1.597958 1.318544 0.051990 N 1.991771 -2.185713 0.000563 C 0.608411 -2.074151 -0.004209 N 0.185926 -0.825722 0.014980 N 0.581298 2.224626 0.088800 H 4.877022 1.254987 0.046448 H 2.541085 -3.036521 -0.013608 H -0.026244 -2.951044 -0.022129 H -0.367027 1.901386 -0.048986 H 0.802985 3.203730 -0.037691 Adenine (COSMO), -2306.9370 N 2.878452 1.761785 0.062667 C 3.872292 0.846889 0.047103 N 3.778186 -0.495229 0.025619 C 2.489616 -0.901302 0.018092 C 1.355996 -0.071959 0.028205 C 1.590604 1.323768 0.053205 N 1.988921 -2.185176 0.000963 C 0.615475 -2.083245 0.001182 N 0.186027 -0.829168 0.017395 N 0.585250 2.229337 0.049322 H 4.881254 1.253691 0.053934 H 2.526907 -3.044843 -0.009156 H -0.013002 -2.963087 -0.012358 H -0.372556 1.918529 0.149643 H 0.793712 3.212759 0.173734 1a (gas phase), -2368.9930 C 2.910830 1.788554 0.060421 C 4.006445 0.896230 0.047587 C 3.826607 -0.487944 0.026373 C 2.497998 -0.937006 0.018602 C 1.373527 -0.068838 0.031130 C 1.590098 1.324563 0.052530 N 1.940496 -2.210228 -0.001149 C 0.564182 -2.052446 0.000002 N 0.183716 -0.795683 0.019209 O 0.492785 2.156673 0.064432 H 5.013522 1.304705 0.054565 H -0.098528 -2.909233 -0.013917 H 0.804500 3.078207 0.078449 H 4.671297 -1.171916 0.016544 H 3.091225 2.862957 0.076812 H 2.445216 -3.086684 -0.014018 1a (COSMO), -2382.7479

  33

C 2.913703 1.794355 0.061598 C 4.007533 0.895181 0.048006 C 3.825027 -0.490338 0.025597 C 2.495117 -0.938650 0.018203 C 1.376426 -0.064014 0.032499 C 1.595029 1.327981 0.053385 N 1.935244 -2.207892 -0.001655 C 0.572412 -2.060403 0.001381 N 0.183549 -0.793676 0.022068 O 0.491428 2.159673 0.064507 H 5.015490 1.301089 0.055220 H -0.086709 -2.918189 -0.012785 H 0.796975 3.085773 0.076424 H 4.663899 -1.180121 0.015128 H 3.090613 2.868107 0.078874 H 2.436801 -3.088085 -0.015323 1b (gas phase), -2267.7262 C 2.909282 1.758049 0.059981 C 3.956987 0.816337 0.046400 N 3.788870 -0.519561 0.025902 C 2.501272 -0.879170 0.019456 C 1.346970 -0.050147 0.031240 C 1.569182 1.337507 0.052571 N 1.993158 -2.169047 -0.000599 C 0.613583 -2.057992 0.000066 N 0.184070 -0.813637 0.018728 O 0.499507 2.190412 0.064785 H 4.986346 1.169999 0.052559 H -0.020683 -2.935700 -0.013796 H 0.826874 3.107263 0.079012 H 3.143418 2.821559 0.076374 H 2.546603 -3.016894 -0.013120 1b (COSMO), -2282.2711 C 2.911589 1.764959 0.060544 C 3.956706 0.823781 0.046507 N 3.788118 -0.518544 0.025607 C 2.497882 -0.886371 0.019235 C 1.352981 -0.047794 0.031321 C 1.573786 1.338976 0.052763 N 1.984406 -2.170970 -0.000664 C 0.616181 -2.063982 0.000050 N 0.185644 -0.810151 0.018908 O 0.499985 2.184795 0.064560 H 4.984985 1.177365 0.052354 H -0.016325 -2.941107 -0.014329 H 0.816368 3.108220 0.075561 H 3.139757 2.827992 0.077723 H 2.519303 -3.032272 -0.012733 2a (gas phase), -2726.1592 N -0.461012 0.063648 0.421309 C 2.436371 2.137819 0.278496 C 3.449331 1.232045 -0.076909 C 3.190338 -0.134370 -0.285310 C 1.906425 -0.670202 -0.150287 C 0.901775 0.236415 0.203754 C 1.120292 1.627884 0.424405 N -0.086701 2.256173 0.763605 C -0.984985 1.299751 0.749148

  34

O 2.832132 3.437993 0.449341 H 4.015489 -0.786846 -0.558844 H -2.038524 1.426402 0.966192 H 2.408082 5.372899 0.888367 C 1.846689 4.436892 0.816471 H 1.063572 4.508167 0.053591 H 1.379052 4.186687 1.775140 H 4.457522 1.621836 -0.188812 H -0.971534 -0.806510 0.351728 H 1.704920 -1.725972 -0.311101 2a (COSMO), -2734.9821 N -0.458269 0.060031 0.422263 C 2.435312 2.138381 0.275583 C 3.448391 1.231285 -0.078464 C 3.189202 -0.138785 -0.284273 C 1.904005 -0.670682 -0.145956 C 0.899227 0.238686 0.206858 C 1.117440 1.633266 0.423983 N -0.097507 2.253835 0.759850 C -0.991402 1.280239 0.743868 O 2.839268 3.444172 0.441674 H 4.014058 -0.791643 -0.556650 H -2.045526 1.397022 0.957964 H 2.427024 5.383423 0.901843 C 1.860131 4.452490 0.827878 H 1.076085 4.534384 0.068626 H 1.407691 4.196011 1.791026 H 4.458869 1.615908 -0.192786 H -0.967258 -0.813104 0.353457 H 1.693203 -1.724549 -0.302215 2b (gas phase), -2625.9141 N -0.401500 0.039600 0.406100 C 2.437000 2.159800 0.282400 C 3.422800 1.218900 -0.074600 C 3.099800 -0.131400 -0.268200 N 1.862100 -0.655500 -0.139300 C 0.952700 0.259500 0.198800 C 1.124000 1.655700 0.428800 N -0.099400 2.246100 0.763800 C -0.965300 1.255800 0.737200 O 2.847700 3.444800 0.447700 H 3.887200 -0.830400 -0.543500 H -2.023200 1.349300 0.948700 H 2.423500 5.383900 0.888200 C 1.861000 4.449300 0.816500 H 1.080100 4.516900 0.051700 H 1.396000 4.194700 1.774700 H 4.447000 1.559700 -0.198700 H -0.865100 -0.856700 0.323300 2b (COSMO), -2635.4476 N -0.403500 0.037700 0.407400 C 2.434700 2.159200 0.281300 C 3.423700 1.219500 -0.075600 C 3.105800 -0.129900 -0.268400 N 1.863800 -0.654800 -0.137700 C 0.944900 0.259100 0.201100 C 1.121500 1.656900 0.428500 N -0.106400 2.242700 0.762000

  35

C -0.971500 1.242600 0.734700 O 2.851300 3.443900 0.444200 H 3.894400 -0.826400 -0.542900 H -2.029100 1.328300 0.944200 H 2.445000 5.391000 0.892400 C 1.872800 4.464200 0.821400 H 1.096400 4.540400 0.054600 H 1.418000 4.209600 1.783100 H 4.448600 1.557500 -0.200900 H -0.882300 -0.852300 0.327400 3a (gas phase), -2227.5981 C 2.894313 1.800409 0.060725 C 3.993469 0.909944 0.047767 C 3.816673 -0.475358 0.026477 C 2.494061 -0.938537 0.018555 C 1.361422 -0.076611 0.030936 C 1.596982 1.306271 0.052382 N 1.941843 -2.214225 -0.001202 C 0.565779 -2.062350 0.000156 N 0.176405 -0.807315 0.018541 F 0.542853 2.172433 0.065050 H 4.999512 1.320210 0.054656 H -0.093031 -2.922119 -0.013068 H 4.666143 -1.153674 0.016657 H 3.045863 2.875735 0.077243 H 2.449320 -3.089409 -0.014031 3a (COSMO), -2237.1934 C 2.896885 1.805819 0.060921 C 3.994821 0.909305 0.047615 C 3.813350 -0.476377 0.026017 C 2.489478 -0.938541 0.018215 C 1.360891 -0.071740 0.030382 C 1.603479 1.307323 0.052060 N 1.936708 -2.210030 -0.000536 C 0.574269 -2.070031 0.000250 N 0.174521 -0.805421 0.018714 F 0.533497 2.176279 0.065523 H 5.001319 1.317528 0.054603 H -0.079644 -2.931687 -0.013276 H 4.656442 -1.161076 0.016058 H 3.053151 2.880337 0.078349 H 2.443051 -3.087750 -0.013343 3b (gas phase), -2124.9812 C 2.888828 1.771405 0.060215 C 3.941204 0.830716 0.046483 N 3.774014 -0.505438 0.025960 C 2.492986 -0.878226 0.019481 C 1.328970 -0.055166 0.031348 C 1.571473 1.321212 0.052531 N 1.990480 -2.170345 -0.000568 C 0.611273 -2.065638 0.000190 N 0.172047 -0.823697 0.018898 F 0.545923 2.210274 0.065496 H 4.969654 1.185451 0.052536 H -0.018705 -2.946454 -0.013652 H 3.095107 2.837432 0.076633 H 2.546821 -3.016708 -0.013161

  36

3b (COSMO), -2134.9299 C 2.892333 1.777088 0.059941 C 3.943096 0.836370 0.046369 N 3.772915 -0.503973 0.026231 C 2.489646 -0.884903 0.019359 C 1.333225 -0.052551 0.030619 C 1.579522 1.320090 0.052116 N 1.982474 -2.170867 0.000085 C 0.614719 -2.070658 0.000214 N 0.173082 -0.819479 0.018241 F 0.541285 2.206157 0.066280 H 4.970186 1.191697 0.052085 H -0.012535 -2.951507 -0.014325 H 3.101386 2.841938 0.076952 H 2.521403 -3.030002 -0.011352 4a (gas phase), -2183.8847 C 3.007823 1.715367 0.059669 C 4.084833 0.800853 0.046196 C 3.876663 -0.579684 0.024818 C 2.545090 -1.009532 0.017405 C 1.433972 -0.118201 0.030397 C 1.687570 1.265298 0.051816 N 1.966966 -2.273070 -0.002371 C 0.595520 -2.090079 -0.000214 N 0.236173 -0.826315 0.018731 CL 0.350887 2.412813 0.068716 H 5.099525 1.189195 0.052773 H -0.083225 -2.934220 -0.013336 H 4.709525 -1.278468 0.014577 H 3.203868 2.783063 0.076418 H 2.455930 -3.158810 -0.015736 4a (COSMO), -2193.9073 C 3.012418 1.717771 0.060106 C 4.087745 0.797421 0.046251 C 3.874025 -0.582911 0.024463 C 2.541332 -1.011122 0.017038 C 1.433080 -0.115858 0.030026 C 1.694314 1.264624 0.051874 N 1.964123 -2.270896 -0.002000 C 0.606076 -2.101741 -0.000135 N 0.235048 -0.828384 0.018658 CL 0.345989 2.419021 0.068906 H 5.102889 1.183308 0.052933 H -0.067191 -2.948314 -0.012799 H 4.699744 -1.288467 0.014033 H 3.213595 2.784425 0.077309 H 2.453073 -3.158560 -0.014115 4b (gas phase), -2081.0412 C 2.999871 1.682680 0.059123 C 4.032099 0.721815 0.044951 N 3.839532 -0.610984 0.024344 C 2.552351 -0.955794 0.018290 C 1.407901 -0.104335 0.030715 C 1.662907 1.273166 0.052044 N 2.024374 -2.237343 -0.001728 C 0.648380 -2.102331 -0.000456 N 0.238046 -0.850681 0.018553 CL 0.353889 2.441652 0.069239

  37

H 5.067108 1.057151 0.050712 H -0.001253 -2.968778 -0.014161 H 3.246075 2.739708 0.075521 H 2.563031 -3.095101 -0.014608 4b (COSMO), -2091.0848 C 3.003288 1.688035 0.059560 C 4.034368 0.727433 0.044832 N 3.837905 -0.608646 0.024005 C 2.548879 -0.961821 0.018201 C 1.410653 -0.102097 0.030794 C 1.669811 1.272142 0.052373 N 2.017935 -2.237351 -0.001613 C 0.653414 -2.109004 -0.000493 N 0.238937 -0.848568 0.018676 CL 0.350244 2.441106 0.068856 H 5.067932 1.063504 0.050082 H 0.007633 -2.976302 -0.014680 H 3.252357 2.743777 0.076455 H 2.540267 -3.106720 -0.015185 5a (gas phase), -2170.2118 C 3.132680 1.603273 0.057926 C 4.192064 0.667085 0.044184 C 3.956603 -0.708994 0.022868 C 2.617147 -1.113718 0.015751 C 1.522175 -0.200873 0.029389 C 1.805511 1.175927 0.051108 N 2.016227 -2.366612 -0.004255 C 0.648670 -2.158713 -0.001341 N 0.312507 -0.888693 0.018428 BR 0.363983 2.462673 0.069606 H 5.214151 1.035887 0.050566 H -0.045381 -2.990277 -0.014402 H 4.775752 -1.423902 0.012445 H 3.353759 2.665951 0.074164 H 2.489043 -3.261141 -0.018190 5a (COSMO), -2180.1373 C 3.138013 1.603854 0.058647 C 4.195709 0.661994 0.044450 C 3.954795 -0.713739 0.022223 C 2.614214 -1.116676 0.015028 C 1.521502 -0.200388 0.029172 C 1.812193 1.173870 0.051025 N 2.015153 -2.366070 -0.004327 C 0.660477 -2.173111 -0.001087 N 0.312019 -0.893543 0.018447 BR 0.360618 2.468202 0.069822 H 5.218151 1.028573 0.051159 H -0.027664 -3.007782 -0.013082 H 4.766522 -1.435461 0.011357 H 3.363987 2.665365 0.075888 H 2.488922 -3.261904 -0.017785 5b (gas phase), -2067.3372 C 3.117740 1.572169 0.057502 C 4.134149 0.592973 0.042877 N 3.918845 -0.735974 0.022235 C 2.626573 -1.059983 0.016570 C 1.495198 -0.188862 0.029467

  38

C 1.775673 1.182620 0.050825 N 2.078390 -2.333036 -0.003396 C 0.704992 -2.176226 -0.001670 N 0.314779 -0.918258 0.017587 BR 0.359010 2.487401 0.070350 H 5.174615 0.911317 0.048315 H 0.041649 -3.032199 -0.015246 H 3.386327 2.623630 0.073881 H 2.603579 -3.199189 -0.016524 5b (COSMO), -2077.3123 C 3.122880 1.576413 0.057840 C 4.137535 0.596809 0.042873 N 3.917545 -0.735235 0.022112 C 2.622950 -1.066660 0.016459 C 1.498175 -0.186736 0.028923 C 1.783307 1.181760 0.050722 N 2.071386 -2.333358 -0.002881 C 0.709316 -2.182720 -0.001687 N 0.315581 -0.915853 0.017037 BR 0.357396 2.487637 0.070398 H 5.176668 0.915514 0.046844 H 0.049470 -3.039322 -0.015002 H 3.394829 2.626381 0.074845 H 2.579669 -3.211086 -0.015919 6a (gas phase), -2492.8147 C 2.909868 1.787509 0.050679 C 4.001675 0.892566 0.039008 C 3.833952 -0.495944 0.029937 C 2.505290 -0.947347 0.028746 C 1.393706 -0.072347 0.037134 C 1.582192 1.328396 0.053528 N 1.933242 -2.216648 0.002101 C 0.558662 -2.047911 -0.009754 N 0.193821 -0.784403 0.009397 N 0.476358 2.176218 0.118997 H 5.008383 1.302997 0.037269 H 2.427527 -3.098889 -0.013408 H -0.111748 -2.898210 -0.033095 H -0.401880 1.736911 -0.140930 H 0.604211 3.103636 -0.269575 H 4.682767 -1.174426 0.020200 H 3.097377 2.859733 0.065086 6a (COSMO), -2504.0838 C 2.908447 1.787571 0.053062 C 4.001880 0.890830 0.044083 C 3.830140 -0.498116 0.028433 C 2.499263 -0.947255 0.022060 C 1.385990 -0.070367 0.033370 C 1.577628 1.331739 0.050444 N 1.935770 -2.216362 -0.001306 C 0.572163 -2.065866 -0.004462 N 0.189314 -0.797182 0.016271 N 0.480809 2.197904 0.120786 H 5.008841 1.300420 0.045947 H 2.434479 -3.098131 -0.016558 H -0.088555 -2.922414 -0.021715 H -0.385582 1.807240 -0.240648 H 0.655330 3.136066 -0.228632

  39

H 4.672126 -1.184022 0.018481 H 3.092751 2.859981 0.062882 6b (gas phase), -2392.4489 C 2.909179 1.756482 0.051650 C 3.952220 0.812501 0.040849 N 3.796244 -0.528720 0.028828 C 2.506936 -0.887794 0.026789 C 1.366529 -0.054076 0.037094 C 1.560787 1.342398 0.052589 N 1.984931 -2.175322 0.000846 C 0.606516 -2.053648 -0.007346 N 0.192559 -0.801701 0.013187 N 0.485882 2.206238 0.107544 H 4.980976 1.168822 0.041028 H 2.528201 -3.029551 -0.015755 H -0.035717 -2.925125 -0.029195 H -0.418374 1.804679 -0.115874 H 0.630859 3.162345 -0.191297 H 3.151448 2.817343 0.064723 6b (COSMO), -2405.2640 C 2.908061 1.758883 0.053196 C 3.950370 0.820840 0.043682 N 3.794282 -0.527331 0.028397 C 2.500037 -0.893042 0.022647 C 1.361921 -0.054475 0.032236 C 1.554753 1.345339 0.049969 N 1.983706 -2.178559 0.000264 C 0.614443 -2.069817 -0.003518 N 0.190331 -0.813457 0.015435 N 0.499260 2.221755 0.106741 H 4.977704 1.178821 0.045936 H 2.516675 -3.040971 -0.012765 H -0.019390 -2.945972 -0.020992 H -0.415647 1.866653 -0.149257 H 0.673307 3.190481 -0.136511 H 3.143824 2.820123 0.063501