Table S1. Cartesian coordinates of methane-benzene dimer (1) at 3.8 angstroms C 1.405707 0.000000 0.647463 C 0.702854 -1.217378 0.647463 C 0.702854 1.217378 0.647463 C -0.702854 -1.217378 0.647463 C -0.702854 1.217378 0.647463 C -1.405707 0.000000 0.647463 C 0.000000 0.000000 -3.152557 H 2.500913 0.000000 0.647463 H 1.250457 -2.165854 0.647463 H 1.250457 2.165854 0.647463 H -1.250457 -2.165854 0.647463 H -1.250457 2.165854 0.647463 H -2.500913 0.000000 0.647463 H 1.036624 0.000000 -3.519058 H -0.518312 0.897743 -3.519058 H -0.518312 -0.897743 -3.519058 H 0.000000 0.000000 -2.053051 Table S2. Cartesian coordinates of methane-phenol dimer (2) at 3.8 angstroms C -1.123839 0.431589 0.016143 C -0.705086 -0.117800 -1.209268 C 0.145389 -1.236224 -1.224499 C 0.582757 -1.812677 -0.021292 C 0.160865 -1.259156 1.200929 C -0.687899 -0.142990 1.223810 O -1.951511 1.519951 0.101270 H -2.300026 1.979103 -0.676730 H -1.024461 0.298613 2.165068 H 0.494071 -1.698355 2.147109 H 1.245035 -2.683609 -0.034995 H 0.464486 -1.654840 -2.184847 H -1.042951 0.327519 -2.149954 C 2.754282 1.609551 0.000926 H 1.879073 0.944032 0.000218 H 2.418603 2.656476 0.014149 H 3.366073 1.409545 0.892338 H 3.353378 1.428150 -0.903002 Table S3. Cartesian coordinates of indole-methane dimer (3a) at 3.8 angstroms C 0.494092 0.278257 -0.766642 C 0.503417 0.327040 0.665426 C -0.608664 0.763444 1.413814 C -1.747034 1.156346 0.703816 C -1.779384 1.116461 -0.716535 C -0.676056 0.683619 -1.455528 C 1.782425 -0.210671 -1.177247 C 2.513866 -0.437571 -0.020214 C -1.951691 -2.842700 0.074133 N 1.742893 -0.113809 1.080520 H 2.043982 -0.189417 2.044793 H 3.531768 -0.807437 0.106078 H 2.133305 -0.376887 -2.195681 H -0.712359 0.657061 -2.550236 H -2.689433 1.432257 -1.237555 H -2.629688 1.501075 1.252733 H -0.585184 0.794731 2.508817 H -1.572295 -1.811408 0.036532 H -1.244226 -3.512304 -0.435810 H -2.929178 -2.892110 -0.426864 H -2.061067 -3.154978 1.122674 Table S4. Cartesian coordinates of indole-methane dimer (3b) at 3.8 angstroms C -0.062096 0.415197 -0.774735 C -0.070226 0.484198 0.656509 C -1.185029 0.092865 1.425490 C -2.308246 -0.375164 0.737241 C -2.323151 -0.452440 -0.681858 C -1.217166 -0.064026 -1.441284 C 1.223843 0.889405 -1.209404 C 1.937032 1.222152 -0.066663 C 2.167439 -2.650541 0.104558 N 1.157101 0.977439 1.048084 H 1.444746 1.136707 2.006253 H 2.947564 1.617413 0.040412 H 1.585088 0.977133 -2.233981 H -1.239957 -0.127936 -2.534812 H -3.221653 -0.824469 -1.185512 H -3.192512 -0.687823 1.302523 H -1.174990 0.151881 2.519555 H 1.772116 -1.625860 0.052911 H 2.581263 -2.833647 1.106627 H 2.959498 -2.776142 -0.647630 H 1.356880 -3.366514 -0.093676 Table S5. Cartesian coordinates of indole-methane dimer (3c) at 3.5 angstroms C 0.185243 0.374325 -0.779679 C 0.183899 0.469409 0.650091 C -1.003295 0.426715 1.409041 C -2.206957 0.285800 0.712123 C -2.230163 0.189583 -0.705706 C -1.052340 0.232173 -1.455184 C 1.557009 0.453844 -1.203222 C 2.324896 0.590542 -0.055669 C 0.450151 -2.960275 0.160377 N 1.497278 0.599265 1.051494 H 1.809536 0.687673 2.011115 H 3.405175 0.683051 0.059709 H 1.937734 0.415794 -2.223786 H -1.082303 0.157075 -2.547828 H -3.192774 0.079999 -1.216342 H -3.148873 0.248944 1.269492 H -0.986956 0.500771 2.502115 H 0.498894 -3.532168 1.098184 H 0.500578 -3.651310 -0.693348 H 1.295567 -2.258786 0.114521 H -0.494436 -2.398836 0.122152 Table S6. Methane-Benzene Dimer (1) Potential Energy Curves Counterpoise-corrected R (methane carbon to center) Binding Energy (Angstroms) (kcal/mol) aug-cc-pVXZ MP2/DZ MP2/TZ CCSD(T)/DZ Est.'d CCSD(T)/TZ ------------------------------------------------------------------------- 3.1 2.327 1.335 3.349 2.357 3.2 0.919 0.118 1.781 0.980 3.3 -0.059 -0.700 0.668 0.027 3.4 -0.713 -1.225 -0.099 -0.611 3.5 -1.128 -1.535 -0.609 -1.016 3.6 -1.371 -1.693 -0.928 -1.250 3.7 -1.488 -1.744 -1.110 -1.366 3.8 -1.519 -1.723 -1.195 -1.399 3.9 -1.493 -1.655 -1.214 -1.376 4.0 -1.429 -1.558 -1.188 -1.318 4.1 -1.342 -1.447 -1.135 -1.239 4.2 -1.246 -1.329 -1.066 -1.149 4.4 -1.045 -1.097 -0.908 -0.959 4.6 -0.859 -0.891 -0.751 -0.784 4.8 -0.697 -0.717 -0.612 -0.633 5.0 -0.562 -0.575 -0.495 -0.508 5.2 -0.453 -0.461 -0.399 -0.407 5.4 -0.365 -0.370 -0.322 -0.327 5.6 -0.295 -0.298 -0.260 -0.263 6.0 -0.196 -0.198 -0.172 -0.174 Table S6 (continued). Methane-Benzene Dimer (1) Potential Energy Curves Counterpoise-corrected R (methane carbon to center) Binding Energy (Angstroms) (kcal/mol) aug-cc-pVXZ MP2/QZ Est.'d CCSD(T)/QZ MP2/CBS Est.'d CCSD(T)/CBS ---------------------------------------------------------------------------------- 3.1 1.125 2.147 0.972 1.994 3.2 -0.051 0.811 -0.172 0.690 3.3 -0.838 -0.110 -0.935 -0.208 3.4 -1.335 -0.721 -1.413 -0.799 3.5 -1.622 -1.103 -1.683 -1.164 3.6 -1.756 -1.314 -1.799 -1.357 3.7 -1.793 -1.415 -1.828 -1.450 3.8 -1.763 -1.439 -1.790 -1.466 3.9 -1.686 -1.407 -1.706 -1.428 4.0 -1.575 -1.334 -1.585 -1.344 4.1 -1.452 -1.245 -1.455 -1.248 4.2 -1.331 -1.150 -1.331 -1.150 4.4 -1.096 -0.958 -1.094 -0.956 4.6 -0.881 -0.774 -0.874 -0.767 4.8 -0.702 -0.618 -0.692 -0.608 5.0 -0.556 -0.489 -0.542 -0.476 5.2 -0.439 -0.385 -0.424 -0.370 5.4 -0.333 -0.290 -0.333 -0.290 5.6 -0.281 -0.246 -0.269 -0.234 6.0 -0.180 -0.156 -0.167 -0.143 Table S7. Methane-Phenol Dimer (2) Potential Energy Curves Counterpoise-corrected R (methane carbon to center) Binding Energy (Angstroms) (kcal/mol) aug-cc-pVXZ MP2/DZ MP2/TZ CCSD(T)/DZ Est.'d CCSD(T)/TZ ------------------------------------------------------------------------- 3.1 2.122 1.155 3.133 2.166 3.2 0.742 -0.038 1.592 0.811 3.3 -0.213 -0.835 0.504 -0.118 3.4 -0.845 -1.340 -0.240 -0.736 3.5 -1.240 -1.633 -0.729 -1.122 3.6 -1.465 -1.776 -1.031 -1.341 3.7 -1.567 -1.814 -1.198 -1.444 3.8 -1.585 -1.781 -1.270 -1.466 3.9 -1.547 -1.704 -1.277 -1.433 4.0 -1.475 -1.599 -1.242 -1.366 4.1 -1.382 -1.481 -1.181 -1.280 4.2 -1.279 -1.358 -1.105 -1.183 4.4 -1.069 -1.119 -0.936 -0.986 4.6 -0.877 -0.906 -0.774 -0.803 4.8 -0.713 -0.729 -0.630 -0.646 5.0 -0.574 -0.584 -0.509 -0.519 5.2 -0.462 -0.469 -0.410 -0.416 5.6 -0.302 -0.303 -0.268 -0.269 6.2 -0.166 -0.161 -0.147 -0.141 6.6 -0.114 -0.112 -0.101 -0.099 Table S8. Methane-Indole Dimer (3a) Potential Energy Curves Counterpoise-corrected R (methane carbon to center) Binding Energy (Angstroms) (kcal/mol) aug-cc-pVXZ MP2/DZ MP2/TZ CCSD(T)/DZ Est.'d CCSD(T)/TZ ------------------------------------------------------------------------- 3.1 1.456 0.556 2.609 1.708 3.2 0.168 -0.555 1.143 0.420 3.3 -0.710 -1.285 0.118 -0.457 3.4 -1.280 -1.735 -0.576 -1.031 3.5 -1.621 -1.983 -1.023 -1.384 3.6 -1.802 -2.085 -1.289 -1.573 3.7 -1.866 -2.089 -1.426 -1.649 3.8 -1.846 -2.028 -1.473 -1.656 3.9 -1.786 -1.926 -1.459 -1.599 4.0 -1.689 -1.800 -1.406 -1.517 4.2 -1.455 -1.522 -1.239 -1.306 4.4 -1.215 -1.254 -1.048 -1.088 4.6 -0.998 -1.018 -0.867 -0.887 5.0 -0.658 -0.660 -0.575 -0.577 5.4 -0.434 -0.427 -0.379 -0.372 5.8 -0.290 -0.281 -0.253 -0.244 6.2 -0.199 -0.185 -0.172 -0.159 6.6 -0.138 -0.128 -0.120 -0.110 Table S9. Methane-Indole Dimer (3b) Potential Energy Curves Counterpoise-corrected R (methane carbon to center) Binding Energy (Angstroms) (kcal/mol) aug-cc-pVXZ MP2/DZ MP2/TZ CCSD(T)/DZ Est.'d CCSD(T)/TZ ------------------------------------------------------------------------- 3.1 2.085 1.203 3.178 2.295 3.2 0.597 -0.105 1.514 0.813 3.3 -0.408 -0.965 0.364 -0.193 3.4 -1.060 -1.497 -0.408 -0.844 3.5 -1.453 -1.796 -0.902 -1.245 3.6 -1.665 -1.933 -1.196 -1.464 3.7 -1.748 -1.958 -1.349 -1.559 3.8 -1.748 -1.910 -1.406 -1.568 3.9 -1.691 -1.815 -1.397 -1.521 4.0 -1.600 -1.699 -1.347 -1.446 4.2 -1.375 -1.435 -1.183 -1.243 4.4 -1.141 -1.177 -0.995 -1.031 4.6 -0.933 -0.950 -0.818 -0.835 5.0 -0.611 -0.608 -0.537 -0.534 5.4 -0.400 -0.392 -0.351 -0.344 5.8 -0.267 -0.259 -0.233 -0.226 6.2 -0.182 -0.175 -0.158 -0.151 6.6 -0.127 -0.124 -0.110 -0.107 Table S10. Methane-Indole Dimer (3c) Potential Energy Curves Counterpoise-corrected R (methane carbon to center) Binding Energy (Angstroms) (kcal/mol) aug-cc-pVXZ MP2/DZ MP2/TZ CCSD(T)/DZ Est.'d CCSD(T)/TZ ------------------------------------------------------------------------- 2.9 1.421 0.421 2.901 1.901 3.0 -0.183 -0.964 1.062 0.281 3.2 -1.863 -2.344 -0.977 -1.458 3.3 -2.215 -2.593 -1.463 -1.842 3.4 -2.365 -2.666 -1.727 -2.028 3.5 -2.383 -2.622 -1.839 -2.078 3.6 -2.314 -2.504 -1.848 -2.038 3.8 -2.042 -2.162 -1.696 -1.816 4.0 -1.713 -1.788 -1.450 -1.525 4.2 -1.394 -1.441 -1.195 -1.242 4.4 -1.119 -1.148 -0.965 -0.994 4.6 -0.892 -0.909 -0.772 -0.789 5.0 -0.567 -0.569 -0.490 -0.493 5.4 -0.365 -0.359 -0.314 -0.309 5.8 -0.238 -0.235 -0.206 -0.203 6.2 -0.162 -0.152 -0.138 -0.128