Are C-H hydrogen bonding sites important in anion-binding receptors? Substituent effects on the interaction of benzene with ClÑ and NO3Ñ Vyacheslav S. Bryantsev and Benjamin P. Hay Chemical Sciences Division, Pacific Northwest National Laboratory, PO Box 999, Richland, WA 99352 Supporting Information Full citation for NWChem software: Straatsma, T.P.; Apra, E.; Windus, T.L.; Bylaska, E.J.; de Jong, W.; Hirata, S.; Valiev, M.; Hackler, M. T.; Pollack, L.; Harrison, R. J.; Dupuis, M.; Smith, D.M.A; Nieplocha, J.; Tipparaju V.; Krishnan, M.; Auer, A. A.; Brown, E.; Cisneros, G.; Fann, G. I.; Fruchtl, H.; Garza, J.; Hirao, K.; Kendall, R.; Nichols, J.; Tsemekhman, K.; Wolinski, K.; Anchell, J.; Bernholdt, D.; Borowski, P.; Clark, T.; Clerc, D.; Dachsel, H.; Deegan, M.; Dyall, K.; Elwood, D.; Glendening, E.; Gutowski, M.; Hess, A.; Jaffe, J.; Johnson, B.; Ju, J.; Kobayashi, R.; Kutteh, R.; Lin, Z.; Littlefield, R.; Long, X.; Meng, B.; Nakajima, T.; Niu, S.; Rosing, M.; Sandrone, G.; Stave, M.; Taylor, H.; Thomas, G.; van Lenthe, J.; Wong, A.; Zhang, Z.; "NWChem, A Computational Chemistry Package for Parallel Computers, Version 4.6" (2004), Pacific Northwest National Laboratory, Richland, Washington 99352-0999, USA. Cartesian coordinates for optimized complexes 1-4 at the MP2/aug-cc-pVDZ level and single point energies calculated at the MP2/aug-cc-pVTZ level are provided as supporting information. For complex 8 and 9 geometries and total energies are obtained at the B3LYP/DZVP2 level of theory. 1, NO2C6H5-Cl anion -895.7875241612 a.u. C 0.92573 -0.36967 0.00000 C -0.03466 -1.39683 0.00000 C -1.41591 -1.13976 0.00000 C -1.83818 0.20266 0.00000 C -0.90110 1.25377 0.00000 C 0.47833 0.96382 0.00000 N 0.41918 -2.79773 0.00000 O 1.64152 -3.01811 0.00000 O -0.44227 -3.69396 0.00000 H 1.98793 -0.62095 0.00000 H -2.12369 -1.97052 0.00000 H -2.91036 0.42403 0.00000 H -1.18349 2.31300 0.00000 H 1.16458 1.81833 0.00000 Cl 0.42656 4.36664 0.00000 1, CNC6H5-Cl anion -783.6404069370 a.u. C 0.99542 0.75661 0.00000 C 0.06824 1.82642 0.00000 C -1.32299 1.57289 0.00000 C -1.77655 0.24140 0.00000 C -0.86014 -0.82789 0.00000 C 0.52527 -0.56773 0.00000 C 0.54058 3.19074 0.00000 H 2.06792 0.97389 0.00000 H -2.02611 2.41148 0.00000 H -2.85305 0.04083 0.00000 H -1.16500 -1.88079 0.00000 H 1.19270 -1.43734 0.00000 Cl 0.42894 -3.96974 0.00000 N 0.92465 4.31756 0.00000 1, CF3C6H5-Cl anion -1028.2140825564 a.u. C 0.82783 0.03514 0.00721 C -0.15518 1.04765 0.00804 C -1.52427 0.72285 0.00344 C -1.90588 -0.63311 -0.00055 C -0.93386 -1.65055 -0.00079 C 0.43525 -1.31399 0.00311 C 0.29178 2.47553 0.00045 H 1.88817 0.30674 0.01139 H -2.27628 1.51574 0.00462 H -2.96985 -0.89184 -0.00283 H -1.18148 -2.71820 -0.00329 H 1.15151 -2.14326 0.00346 Cl 0.51364 -4.73952 -0.00179 F 0.99191 2.79912 -1.13211 F -0.73888 3.36643 0.07685 F 1.12942 2.76796 1.04321 1, ClC6H5-Cl anion -1150.6677426863 a.u. C 0.96888 0.62556 0.00000 C 0.04725 1.68631 0.00000 C -1.33908 1.46685 0.00000 C -1.80715 0.13633 0.00000 C -0.90488 -0.94389 0.00000 C 0.48192 -0.69600 0.00000 Cl 0.64782 3.35058 0.00000 Cl 0.42693 -4.12661 0.00000 H 2.04223 0.83522 0.00000 H -2.02885 2.31545 0.00000 H -2.88692 -0.04816 0.00000 H -1.22371 -1.99186 0.00000 H 1.14504 -1.56906 0.00000 1, C6H6-Cl anion -691.5379722589 a.u. C 0.00000 1.40615 -1.33848 C 0.00000 0.70441 -2.56199 C 0.00000 -0.70441 -2.56199 C 0.00000 -1.40615 -1.33848 C 0.00000 -0.70454 -0.11705 C 0.00000 0.70454 -0.11705 H 0.00000 -1.20449 0.85799 H 0.00000 1.20449 0.85799 Cl 0.00000 0.00000 3.30580 H 0.00000 2.50193 -1.34071 H 0.00000 1.25183 -3.51147 H 0.00000 -1.25183 -3.51147 H 0.00000 -2.50193 -1.34071 1, CH3C6H5-Cl anion -730.7663555701 a.u. C -1.10546 0.97271 -0.00332 C -0.29602 2.13190 -0.00238 C 1.10454 1.97239 -0.00152 C 1.68364 0.68556 0.00035 C 0.86704 -0.46028 0.00069 C -0.53485 -0.31317 -0.00144 C -0.92666 3.50981 0.00408 H -2.19742 1.08275 -0.00599 H 1.74675 2.86194 -0.00299 H 2.77464 0.58280 0.00030 H 1.26582 -1.48049 0.00136 H -1.13418 -1.23062 -0.00258 Cl -0.23105 -3.78954 0.00071 H -1.50346 3.68049 0.92940 H -0.15798 4.29654 -0.06512 H -1.61967 3.63536 -0.84521 1, NH2C6H5-Cl anion -746.8066963539 a.u. C -1.10672 0.95732 -0.02383 C -0.32524 2.13224 0.00142 C 1.07966 2.02136 0.00485 C 1.68894 0.75012 -0.00589 C 0.90695 -0.41995 -0.02613 C -0.49715 -0.31030 -0.03600 N -0.94667 3.41926 -0.04683 H -1.88623 3.39199 0.34597 H -0.40594 4.11607 0.46290 H -2.20083 1.04049 -0.03214 H 1.69396 2.93037 0.01212 H 2.78255 0.68175 0.00207 H 1.33650 -1.42679 -0.03034 H -1.07359 -1.24256 -0.04643 Cl -0.24108 -3.77711 0.00748 2, NO2C6H5-Cl anion -895.7863688667 a.u. C 0.00000 0.00000 1.49870 C 0.00000 1.23101 0.82174 C 0.00000 1.21294 -0.58494 C 0.00000 0.00000 -1.30279 C 0.00000 -1.21294 -0.58494 C 0.00000 -1.23101 0.82174 N 0.00000 0.00000 2.97095 O 0.00000 -1.09541 3.55712 O 0.00000 1.09541 3.55712 H 0.00000 2.16312 1.38969 H 0.00000 2.15706 -1.13834 H 0.00000 0.00000 -2.40822 H 0.00000 -2.15706 -1.13834 H 0.00000 -2.16312 1.38969 Cl 0.00000 0.00000 -4.69541 2, CNC6H5-Cl anion -783.6391338579 a.u. C 0.00000 0.00000 -1.95717 C 0.00000 1.22730 -1.25451 C 0.00000 1.21344 0.15128 C 0.00000 0.00000 0.86835 C 0.00000 -1.21344 0.15128 C 0.00000 -1.22730 -1.25451 C 0.00000 0.00000 -3.40083 N 0.00000 0.00000 -4.59110 H 0.00000 2.16893 -1.81209 H 0.00000 2.15715 0.70577 H 0.00000 0.00000 1.97357 H 0.00000 -2.15715 0.70577 H 0.00000 -2.16893 -1.81209 Cl 0.00000 0.00000 4.26785 2, CF3C6H5-Cl anion -1028.2130566372 a.u. C -0.03672 -1.12632 0.00919 C -1.26901 -0.44670 0.00626 C -1.27573 0.96129 0.00289 C -0.07364 1.69484 0.00145 C 1.14975 0.99373 0.00362 C 1.17838 -0.41148 0.00716 C 0.01753 -2.62147 -0.00026 Cl 0.04765 5.11072 -0.00326 H -2.20510 -1.01070 0.00842 H -2.22812 1.50061 0.00204 H -0.08067 2.79929 -0.00060 H 2.08542 1.56138 0.00328 H 2.12980 -0.95269 0.01019 F -1.20938 -3.20851 0.08483 F 0.75817 -3.12449 1.03633 F 0.60069 -3.11629 -1.13780 2, ClC6H5-Cl anion -746.8058859371 a.u. C 0.00000 0.00000 1.81190 C 0.00000 1.22666 1.12899 C 0.00000 1.21129 -0.28042 C 0.00000 0.00000 -0.99976 C 0.00000 -1.21129 -0.28042 C 0.00000 -1.22666 1.12899 Cl 0.00000 0.00000 3.57999 Cl 0.00000 0.00000 -4.44297 H 0.00000 2.16543 1.69007 H 0.00000 2.15777 -0.83071 H 0.00000 0.00000 -2.10346 H 0.00000 -2.15777 -0.83071 H 0.00000 -2.16543 1.69007 2, C6H6-Cl anion -691.5373059750 a.u. C 0.00000 0.00000 2.83008 C 0.00000 1.21827 2.12190 C 0.00000 1.21306 0.71247 C 0.00000 0.00000 -0.00548 C 0.00000 -1.21306 0.71247 C 0.00000 -1.21827 2.12190 H 0.00000 -2.16770 2.66926 H 0.00000 -2.15775 0.15865 H 0.00000 0.00000 -1.10829 H 0.00000 2.15775 0.15865 H 0.00000 2.16770 2.66926 H 0.00000 0.00000 3.92579 Cl 0.00000 0.00000 -3.49609 2, CH3C6H5-Cl anion -730.7656668015 a.u. C 0.01047 -2.30172 -0.00228 C 1.20934 -1.55496 -0.00272 C 1.18167 -0.14742 -0.00149 C -0.04201 0.55318 -0.00041 C -1.23780 -0.19028 -0.00130 C -1.21270 -1.60013 -0.00258 C 0.04678 -3.81654 0.00559 Cl 0.01240 4.04825 0.00119 H 2.17162 -2.08288 -0.00463 H 2.11808 0.42038 -0.00247 H -0.05671 1.65560 -0.00007 H -2.19583 0.34023 -0.00221 H -2.15370 -2.16422 -0.00455 H 0.63746 -4.20670 -0.84069 H -0.96987 -4.23489 -0.06836 H 0.50378 -4.20066 0.93382 2, NH2C6H5-Cl anion -746.8058859371 a.u. C 0.00206 -2.31696 0.00420 C -1.21421 -1.60404 -0.00867 C -1.21182 -0.19572 -0.02428 C -0.00588 0.53234 -0.03156 C 1.20412 -0.18899 -0.02450 C 1.21435 -1.59725 -0.00887 N 0.00603 -3.74570 -0.04086 H 0.83336 -4.13144 0.41123 H -0.81868 -4.13607 0.41205 H -2.16262 -2.15586 -0.00797 H -2.16289 0.34693 -0.02858 H -0.00822 1.63433 -0.03675 H 2.15196 0.35924 -0.02895 H 2.16581 -2.14379 -0.00829 Cl 0.00161 4.03942 0.00796 3, NO2C6H5-NO3 anion -715.9950521859 a.u. C 1.66425 0.44272 0.00208 C 1.37365 1.81935 0.00025 C 0.02384 2.20842 0.00004 C -1.02920 1.27766 0.00157 C -0.70810 -0.09194 0.00342 C 0.63508 -0.51995 0.00369 H 2.70946 0.11749 0.00221 H 2.15825 2.57798 -0.00095 N -0.29615 3.64585 -0.00187 H -2.06269 1.62868 0.00127 H -1.48737 -0.85876 0.00463 H 0.84578 -1.59872 0.00510 N -0.16603 -4.06096 -0.00079 O 1.05280 -3.69223 -0.00017 O -0.45836 -5.28607 -0.00860 O -1.08355 -3.18021 0.00652 O -1.49249 3.97988 -0.00215 O 0.64594 4.45632 -0.00310 3, CNC6H5-NO3 anion -603.8478613063 a.u. C -1.61866 0.90329 0.00000 C -1.30830 2.27480 0.00000 C 0.04821 2.67404 0.00000 C 1.08091 1.70688 0.00000 C 0.74857 0.34110 0.00000 C -0.59983 -0.07043 0.00000 C 0.37770 4.07968 0.00000 N 0.16514 -3.62582 0.00000 O -1.04983 -3.24500 0.00000 O 0.44530 -4.85399 0.00000 O 1.09149 -2.75437 0.00000 H -2.66739 0.58888 0.00000 H -2.09599 3.03439 0.00000 H 2.12518 2.03379 0.00000 H 1.51833 -0.43557 0.00000 H -0.82285 -1.14663 0.00000 N 0.64564 5.23951 0.00000 3, CF3C6H5-NO3 anion -848.4218083973 a.u. C -1.72375 0.00838 0.00157 C -1.45673 1.39109 0.00386 C -0.11967 1.82928 0.00654 C 0.94240 0.90126 0.00587 C 0.65933 -0.47529 0.00348 C -0.67505 -0.93129 0.00131 C 0.20955 3.28892 -0.00023 N 0.20641 -4.47478 -0.00139 O -1.02041 -4.13483 -0.00321 O 0.52733 -5.69354 -0.00135 O 1.10333 -3.57344 0.00040 H -2.76178 -0.33956 0.00045 H -2.27220 2.11852 0.00480 H 1.97702 1.25848 0.00843 H 1.45547 -1.22464 0.00372 H -0.86281 -2.01382 -0.00013 F 1.00718 3.65009 1.05261 F 0.89680 3.66466 -1.12446 F -0.89053 4.09246 0.05978 3, ClC6H5-NO3 anion -970.8755024852 a.u. C -1.63674 -0.77204 0.00000 C -1.32055 -2.14605 0.00000 C 0.03238 -2.52003 0.00000 C 1.06482 -1.56771 0.00000 C 0.72389 -0.20069 0.00000 C -0.62467 0.20753 0.00000 Cl 0.44590 -4.23946 0.00000 N 0.16400 3.79504 0.00000 O -1.05219 3.42016 0.00000 O 0.44956 5.02333 0.00000 O 1.08700 2.92083 0.00000 H -2.68857 -0.46685 0.00000 H -2.10098 -2.91209 0.00000 H 2.10860 -1.89407 0.00000 H 1.49406 0.57588 0.00000 H -0.85122 1.28207 0.00000 3, C6H6-NO3 anion -511.7461038362 a.u. C -1.37507 -1.85087 -0.00720 C -0.93404 -3.18996 0.01019 C 0.44585 -3.47424 0.01841 C 1.37781 -2.41642 0.00919 C 0.93176 -1.08002 -0.00825 C -0.44749 -0.78971 -0.01647 H -2.44837 -1.63143 -0.01332 H -1.66128 -4.00974 0.01740 H 0.79200 -4.51382 0.03201 H 2.45115 -2.63693 0.01570 H 1.63155 -0.23938 -0.01537 H -0.76557 0.26108 -0.02998 N 0.00167 2.89431 -0.00121 O -1.17436 2.40913 -0.01012 O 0.17214 4.14426 0.04544 O 1.00170 2.11129 -0.03946 3, CH3C6H5-NO3 anion -550.9745241938 a.u. C -1.54630 1.27272 -0.00001 C -1.16554 2.63093 0.00282 C 0.19546 2.99850 0.00311 C 1.16683 1.97215 0.00250 C 0.78930 0.61644 -0.00029 C -0.57354 0.25489 -0.00188 C 0.61423 4.45476 -0.00249 N 0.08423 -3.40387 -0.00049 O -1.11709 -2.98536 -0.00311 O 0.32451 -4.64332 0.00599 O 1.03891 -2.56534 -0.00444 H -2.60929 1.00758 0.00050 H -1.93313 3.41475 0.00549 H 2.23076 2.24153 0.00475 H 1.53215 -0.18646 -0.00022 H -0.83978 -0.81008 -0.00342 H 1.28307 4.68104 0.84527 H 1.15631 4.71080 -0.92908 H -0.26287 5.11788 0.07008 3, NH2C6H5-NO3 anion -567.0148839163 a.u. C -1.54436 1.29551 0.00234 C -1.15900 2.65006 -0.04572 C 0.20647 2.99928 -0.03139 C 1.17347 1.97481 0.04169 C 0.78128 0.62407 0.09063 C -0.58196 0.26949 0.07060 H -2.60988 1.04157 -0.01484 H -1.91829 3.44070 -0.09163 N 0.60143 4.37304 -0.01964 H 2.23782 2.24078 0.06004 H 1.52063 -0.18042 0.14028 H -0.85602 -0.79240 0.10546 N 0.08819 -3.38153 0.00341 O -1.11205 -2.97797 0.12330 O 0.32746 -4.59497 -0.25177 O 1.04327 -2.55505 0.14155 H 1.52845 4.49753 -0.42313 H -0.05484 4.95630 -0.53612 4, NO2C6H5-NO3 anion -715.9946220371 a.u. C -0.71474 -0.93315 0.00935 C 0.04187 -2.11765 0.00015 C 1.44688 -2.11799 -0.00695 C 2.10530 -0.87509 -0.00458 C 1.37167 0.32724 0.00465 C -0.03806 0.30135 0.01155 H -1.80503 -0.98506 0.01448 N -0.65883 -3.41404 -0.00211 H 1.99171 -3.06345 -0.01406 H 3.19980 -0.85108 -0.01001 H 1.86102 1.30486 0.00647 H -0.58240 1.25665 0.01821 N -0.33374 3.92938 -0.00129 O -1.37870 3.20236 -0.00326 O -0.43355 5.18481 -0.02142 O 0.81107 3.37527 0.02113 O 0.02714 -4.45073 -0.01203 O -1.90028 -3.40891 0.00605 4, CNC6H5-NO3 anion -603.8476432820 a.u. C -0.82583 1.32119 0.00000 C -0.12149 2.54861 0.00000 C 1.29265 2.56721 0.00000 C 1.99122 1.34721 0.00000 C 1.29286 0.12388 0.00000 C -0.11705 0.10641 0.00000 C -0.84491 3.79834 0.00000 N -0.32697 -3.52963 0.00000 O -1.39122 -2.83101 0.00000 O -0.39328 -4.78759 0.00000 O 0.80251 -2.94483 0.00000 H -1.91999 1.32728 0.00000 H 1.82289 3.52433 0.00000 H 3.08619 1.35479 0.00000 H 1.81207 -0.83829 0.00000 H -0.63229 -0.86494 0.00000 N -1.43268 4.83351 0.00000 4, CF3C6H5-NO3 anion -848.4215875558 a.u. C -0.56941 0.59330 0.00788 C 0.21862 1.76334 0.00922 C 1.62368 1.68667 0.00472 C 2.23730 0.41954 0.00039 C 1.45649 -0.75154 -0.00034 C 0.04865 -0.66979 0.00351 C -0.47308 3.09093 0.00024 N -0.41682 -4.29830 -0.00116 O -1.43101 -3.52931 0.00394 O -0.56866 -5.54945 -0.00289 O 0.74984 -3.79222 -0.00448 H -1.66106 0.67185 0.01213 H 2.22437 2.59935 0.00648 H 3.33011 0.35100 -0.00174 H 1.90766 -1.74742 -0.00321 H -0.53417 -1.60142 0.00354 F -1.35807 3.22669 1.03456 F -1.20576 3.29054 -1.13934 F 0.38561 4.14810 0.08973 4, ClC6H5-NO3 anion -970.8755223945 a.u. C -0.79241 1.18834 0.00000 C -0.08478 2.40190 0.00000 C 1.31837 2.44464 0.00000 C 2.02426 1.22447 0.00000 C 1.33496 -0.00308 0.00000 C -0.07414 -0.02415 0.00000 Cl -0.98271 3.92548 0.00000 N -0.32192 -3.68358 0.00000 O -1.38193 -2.97900 0.00000 O -0.39663 -4.94231 0.00000 O 0.81093 -3.10685 0.00000 H -1.88594 1.19277 0.00000 H 1.83895 3.40618 0.00000 H 3.11950 1.24216 0.00000 H 1.86023 -0.96175 0.00000 H -0.58970 -0.99479 0.00000 4, CH3C6H5-NO3 anion -550.9746024685 a.u. C -1.00131 1.52091 -0.00229 C -0.44254 2.81921 -0.00075 C 0.96143 2.94592 -0.00000 C 1.78632 1.80177 0.00022 C 1.21324 0.51633 -0.00061 C -0.18927 0.37127 -0.00209 C -1.33821 4.04145 0.00404 N -0.14794 -3.34107 0.00002 O -1.26443 -2.73104 -0.00429 O -0.11454 -4.60313 0.00620 O 0.93130 -2.67053 -0.00194 H -2.09264 1.40730 -0.00403 H 1.41210 3.94603 -0.00010 H 2.87588 1.91895 0.00041 H 1.82485 -0.39021 -0.00081 H -0.61645 -0.64018 -0.00352 H -2.02079 4.03826 -0.86269 H -0.74324 4.96829 -0.03475 H -1.96070 4.07539 0.91450 4, NH2C6H5-NO3 anion -567.0151823567 a.u. C -1.00514 1.50515 0.04227 C -0.46460 2.80640 -0.03102 C 0.93562 2.96705 -0.05041 C 1.77582 1.83677 -0.00736 C 1.22988 0.54093 0.06259 C -0.16889 0.37446 0.08843 H -2.09432 1.37506 0.06108 N -1.31936 3.95113 -0.01546 H 1.36482 3.97558 -0.09457 H 2.86236 1.97705 -0.02822 H 1.85926 -0.35230 0.09422 H -0.58431 -0.64053 0.13763 N -0.15378 -3.31503 0.00723 O -1.26327 -2.71519 0.17646 O -0.13478 -4.54508 -0.27736 O 0.93203 -2.66658 0.12601 H -0.93662 4.71562 -0.56909 H -2.24716 3.72720 -0.37125 8, tripodal amide host -1492.0259670805 a.u. N 0.00000 -0.00000 -3.05619 C -0.42083 -1.34352 -3.46764 C -1.51408 -1.94455 -2.56686 N -1.12175 -2.05602 -1.16474 C -0.22425 -2.99503 -0.74132 O 0.25575 -3.84060 -1.50821 C 0.16191 -2.95294 0.71729 C 1.34177 -3.62040 1.08919 C 1.75595 -3.63702 2.42365 C 0.98504 -2.99910 3.40589 C -0.19801 -2.34340 3.04411 C -0.60789 -2.31676 1.70636 H -1.32506 -1.27354 -0.56050 H -0.78591 -1.36030 -4.51109 H 0.43955 -2.01376 -3.42469 H -1.75099 -2.94543 -2.93849 H -2.42948 -1.34816 -2.60295 H 1.90866 -4.13098 0.31769 H 2.67043 -4.15383 2.70084 H 1.29866 -3.02446 4.44596 H -0.80777 -1.85783 3.80020 H -1.54317 -1.82392 1.45863 C 1.37394 0.30731 -3.46764 C -0.95311 1.03621 -3.46764 C 2.44107 -0.33896 -2.56686 C -0.92699 2.28350 -2.56686 N 2.34144 0.05655 -1.16474 N -1.21969 1.99947 -1.16474 C 2.70590 1.30331 -0.74132 C -2.48165 1.69172 -0.74132 O 3.19818 2.14179 -1.50821 O -3.45393 1.69881 -1.50821 C 2.47636 1.61669 0.71729 C -2.63827 1.33625 0.71729 C 2.46448 2.97221 1.08919 C -3.80625 0.64820 1.08919 C 2.27178 3.33921 2.42365 C -4.02773 0.29782 2.42365 C 2.10477 2.35262 3.40589 C -3.08982 0.64648 3.40589 C 2.12845 1.00021 3.04411 C -1.93043 1.34318 3.04411 C 2.31032 0.63193 1.70636 C -1.70243 1.68483 1.70636 H 1.76545 -0.51076 -0.56050 H -0.44039 1.78430 -0.56050 H 1.57101 -0.00047 -4.51109 H -0.78510 1.36077 -4.51109 H 1.52419 1.38754 -3.42469 H -1.96375 0.62622 -3.42469 H 3.42631 -0.04368 -2.93849 H -1.67532 2.98912 -2.93849 H 2.38228 -1.42991 -2.60295 H 0.04720 2.77807 -2.60295 H 2.62321 3.71844 0.31769 H -4.53186 0.41255 0.31769 H 2.26211 4.38958 2.70084 H -4.93254 -0.23574 2.70084 H 1.96993 2.63690 4.44596 H -3.26859 0.38756 4.44596 H 2.01282 0.22936 3.80020 H -1.20504 1.62847 3.80020 H 2.35115 -0.42447 1.45863 H -0.80798 2.24839 1.45863 8, tripodal amide host - NO3 guest complex -1772.5401846359 a.u. N 0.00000 -0.00000 -2.48085 N 0.00000 0.00000 1.27771 C -0.15095 -1.39205 -2.93609 C -1.06427 -2.24779 -2.03703 N -0.38033 -2.81202 -0.87940 C 0.21618 -4.03128 -0.95291 O 0.21362 -4.71479 -1.99374 C 0.88295 -4.55066 0.30007 C 1.12468 -5.93358 0.36890 C 1.74316 -6.49234 1.49042 C 2.14313 -5.66867 2.55284 C 1.91974 -4.28832 2.48028 C 1.29024 -3.72594 1.36232 O -0.90690 -0.88945 1.27604 H -0.42678 -2.29298 -0.00265 H 0.82959 -1.87355 -2.96108 H -0.53754 -1.42285 -3.97252 H -1.90387 -1.64976 -1.67300 H -1.45661 -3.08034 -2.62723 H 0.82424 -6.54648 -0.47459 H 1.91801 -7.56448 1.53689 H 2.63000 -6.09845 3.42482 H 2.23978 -3.64059 3.29195 H 1.14978 -2.64975 1.32927 C 1.28103 0.56530 -2.93609 C -1.13008 0.82675 -2.93609 C 2.47877 0.20221 -2.03703 C -1.41451 2.04557 -2.03703 N 2.62544 1.07663 -0.87940 N -2.24511 1.73538 -0.87940 C 3.38310 2.20286 -0.95291 C -3.59928 1.82842 -0.95291 O 3.97632 2.54239 -1.99374 O -4.18993 2.17240 -1.99374 C 3.49951 3.03998 0.30007 C -4.38246 1.51067 0.30007 C 4.57629 3.94079 0.36890 C -5.70096 1.99279 0.36890 C 4.75096 4.75579 1.49042 C -6.49411 1.73655 1.49042 C 3.83765 4.69035 2.55284 C -5.98078 0.97833 2.55284 C 2.75392 3.80671 2.48028 C -4.67366 0.48161 2.48028 C 2.58164 2.98035 1.36232 C -3.87188 0.74559 1.36232 O 1.22374 -0.34068 1.27604 O -0.31684 1.23013 1.27604 H 2.19917 0.77689 -0.00265 H -1.77239 1.51609 -0.00265 H 1.20775 1.65522 -2.96108 H -2.03734 0.21833 -2.96108 H 1.50100 0.24590 -3.97252 H -0.96345 1.17695 -3.97252 H 2.38067 -0.82392 -1.67300 H -0.47680 2.47368 -1.67300 H 3.39596 0.27871 -2.62723 H -1.93935 2.80163 -2.62723 H 5.25730 3.98705 -0.47459 H -6.08154 2.55943 -0.47459 H 5.59203 5.44329 1.53689 H -7.51004 2.12119 1.53689 H 3.96641 5.32687 3.42482 H -6.59641 0.77158 3.42482 H 2.03295 3.76000 3.29195 H -4.27273 -0.11941 3.29195 H 1.71986 2.32062 1.32927 H -2.86965 0.32913 1.32927 9, tripodal amide host -2105.7064132379 a.u. N 0.00000 -0.00000 3.78949 C -1.40042 -0.03125 4.20411 C -2.22325 -1.20385 3.63643 N -2.06626 -1.46251 2.20874 C -2.50055 -0.60767 1.24990 O -3.00220 0.49840 1.51994 C -2.41318 -1.08969 -0.17999 C -3.18384 -0.39441 -1.11929 C -3.17846 -0.81302 -2.44745 C -2.43837 -1.91670 -2.88091 C -1.65600 -2.59337 -1.94287 C -1.64086 -2.18608 -0.60329 H -1.54426 -2.28268 1.93464 H -1.51043 -0.07101 5.30686 H -1.87931 0.88742 3.86688 H -3.27624 -0.98114 3.83906 H -1.98752 -2.13737 4.15166 H -3.78372 0.45005 -0.80581 N -3.97481 -0.05247 -3.43217 H -2.46945 -2.21469 -3.92201 H -1.05060 -3.43820 -2.25778 H -0.99308 -2.71898 0.08698 O -4.45109 1.03660 -3.07183 O -4.11141 -0.53485 -4.56351 C 0.72728 -1.19717 4.20411 C 0.67314 1.22843 4.20411 C 2.15419 -1.32347 3.63643 C 0.06907 2.52732 3.63643 N 2.29970 -1.05818 2.20874 N -0.23344 2.52068 2.20874 C 1.77653 -1.86171 1.24990 C 0.72402 2.46938 1.24990 O 1.06948 -2.84918 1.51994 O 1.93272 2.35079 1.51994 C 2.15029 -1.54503 -0.17999 C 0.26289 2.63472 -0.17999 C 1.93349 -2.56008 -1.11929 C 1.25035 2.95449 -1.11929 C 2.29333 -2.34612 -2.44745 C 0.88513 3.15914 -2.44745 C 2.87910 -1.15334 -2.88091 C -0.44073 3.07004 -2.88091 C 3.07392 -0.13745 -1.94287 C -1.41792 2.73082 -1.94287 C 2.71363 -0.32798 -0.60329 C -1.07277 2.51406 -0.60329 H 2.74898 -0.19603 1.93464 H -1.20473 2.47870 1.93464 H 0.81671 -1.27257 5.30686 H 0.69372 1.34358 5.30686 H 0.17113 -2.07124 3.86688 H 1.70818 1.18382 3.86688 H 2.48781 -2.34673 3.83906 H 0.78842 3.32788 3.83906 H 2.84478 -0.65256 4.15166 H -0.85725 2.78993 4.15166 H 1.50211 -3.50182 -0.80581 H 2.28161 3.05178 -0.80581 N 2.03285 -3.41605 -3.43217 N 1.94196 3.46852 -3.43217 H 3.15270 -1.03126 -3.92201 H -0.68325 3.24595 -3.92201 H 3.50287 0.80925 -2.25778 H -2.45226 2.62895 -2.25778 H 2.85125 0.49945 0.08698 H -1.85816 2.21953 0.08698 O 1.32782 -4.37306 -3.07183 O 3.12327 3.33646 -3.07183 O 2.51890 -3.29316 -4.56351 O 1.59252 3.82801 -4.56351 9, tripodal amide host - NO3 guest complex -2386.2421930867 a.u. N 0.00000 -0.00000 2.88864 N 0.00000 0.00000 -0.89553 C -1.22719 -0.67324 3.34867 C -1.66450 -1.85140 2.45875 N -2.42313 -1.44335 1.28047 C -3.77770 -1.35798 1.32759 O -4.43573 -1.60318 2.35165 C -4.48746 -0.95933 0.05076 C -5.84762 -1.28556 -0.03843 C -6.55642 -0.93315 -1.18592 C -5.96036 -0.24384 -2.24917 C -4.61101 0.09141 -2.13998 C -3.87151 -0.26322 -1.00303 O -0.46383 -1.18223 -0.89380 H -1.91056 -1.30004 0.41080 H -1.10715 -1.03622 4.38631 H -2.04931 0.04617 3.36990 H -2.30158 -2.51724 3.04662 H -0.79212 -2.41509 2.11791 H -6.33116 -1.79737 0.78400 N -7.98404 -1.29177 -1.28376 H -6.54979 0.01685 -3.11953 H -4.12476 0.63760 -2.94278 H -2.82791 0.03205 -0.94919 O -8.49856 -1.91382 -0.34256 O -8.60014 -0.95195 -2.30844 C 1.19664 -0.72616 3.34867 C 0.03055 1.39940 3.34867 C 2.43561 -0.51580 2.45875 C -0.77111 2.36720 2.45875 N 2.46154 -1.37682 1.28047 N -0.03841 2.82016 1.28047 C 3.06490 -2.59259 1.32759 C 0.71280 3.95058 1.32759 O 3.60626 -3.03986 2.35165 O 0.82947 4.64304 2.35165 C 3.07453 -3.40659 0.05076 C 1.41293 4.36592 0.05076 C 4.03714 -4.42141 -0.03843 C 1.81048 5.70697 -0.03843 C 4.08635 -5.21145 -1.18592 C 2.47008 6.14460 -1.18592 C 3.19135 -5.03991 -2.24917 C 2.76901 5.28375 -2.24917 C 2.22634 -4.03896 -2.13998 C 2.38467 3.94754 -2.13998 C 2.16371 -3.22122 -1.00303 C 1.70780 3.48444 -1.00303 O 1.25576 0.18943 -0.89380 O -0.79193 0.99281 -0.89380 H 2.08114 -1.00457 0.41080 H -0.17059 2.30461 0.41080 H 1.45097 -0.44071 4.38631 H -0.34382 1.47693 4.38631 H 0.98466 -1.79784 3.36990 H 1.06464 1.75166 3.36990 H 3.33078 -0.73460 3.04662 H -1.02921 3.25184 3.04662 H 2.48759 0.52155 2.11791 H -1.69547 1.89354 2.11791 H 4.72215 -4.58426 0.78400 H 1.60901 6.38163 0.78400 N 5.11072 -6.26850 -1.28376 N 2.87332 7.56026 -1.28376 H 3.26030 -5.68071 -3.11953 H 3.28949 5.66386 -3.11953 H 1.51020 -3.89095 -2.94278 H 2.61456 3.25335 -2.94278 H 1.38620 -2.46507 -0.94919 H 1.44172 2.43302 -0.94919 O 5.90670 -6.40306 -0.34256 O 2.59186 8.31688 -0.34256 O 5.12448 -6.97196 -2.30844 O 3.47565 7.92392 -2.30844 benzene -231.7428114069 a.u. C -0.47950 1.32377 0.00000 C 0.90667 1.07714 0.00000 C 1.38617 -0.24663 0.00000 C 0.47950 -1.32377 0.00000 C -0.90667 -1.07714 0.00000 C -1.38617 0.24663 0.00000 H -1.61116 -1.91451 0.00000 H -2.46359 0.43805 0.00000 H -0.85243 2.35256 0.00000 H 1.61116 1.91451 0.00000 H 2.46359 -0.43805 0.00000 H 0.85243 -2.35256 0.00000 NO2C6H5 -435.9800216696 a.u. C 0.00000 0.00000 -0.24732 C -0.00293 1.23115 0.42513 C -0.00296 1.21914 1.83089 C 0.00000 0.00000 2.53500 C 0.00296 -1.21914 1.83089 C 0.00293 -1.23115 0.42513 N 0.00000 0.00000 -1.72648 O -0.00632 -1.09808 -2.30034 O 0.00632 1.09808 -2.30034 H -0.00602 2.16208 -0.14402 H -0.00518 2.16728 2.37599 H 0.00000 0.00000 3.62868 H 0.00518 -2.16728 2.37599 H 0.00602 -2.16208 -0.14402 CNC6H5 -323.8334844132 a.u. C 0.00000 0.00000 -0.60912 C 0.00000 1.22746 0.09086 C 0.00000 1.21946 1.49549 C 0.00000 0.00000 2.19916 C 0.00000 -1.21946 1.49549 C 0.00000 -1.22746 0.09086 C 0.00000 0.00000 -2.05353 N 0.00000 0.00000 -3.24289 H 0.00000 2.16867 -0.46537 H 0.00000 2.16737 2.04137 H 0.00000 0.00000 3.29292 H 0.00000 -2.16737 2.04137 H 0.00000 -2.16867 -0.46537 CF3C6H5 -568.4106919428 a.u. C -0.02446 -0.04889 0.01015 C -1.23794 -0.75809 0.00606 C -1.21223 -2.16464 -0.00073 C 0.01548 -2.85124 -0.00412 C 1.22578 -2.13082 -0.00062 C 1.21011 -0.72651 0.00637 C -0.01060 1.45431 0.00111 H -2.18784 -0.21934 0.01009 H -2.15232 -2.72372 -0.00231 H 0.03034 -3.94496 -0.00855 H 2.18118 -2.66319 -0.00211 H 2.14548 -0.16000 0.01074 F -1.25112 1.99403 0.11390 F 0.53319 1.94464 -1.14967 F 0.73863 1.95760 1.02275 ClC6H5 -690.8671133584 a.u. C 0.00000 0.00000 0.51259 C 0.00000 1.22627 -0.17305 C 0.00000 1.21723 -1.58012 C 0.00000 0.00000 -2.28662 C 0.00000 -1.21723 -1.58012 C 0.00000 -1.22627 -0.17305 Cl 0.00000 0.00000 2.26674 H 0.00000 2.16503 0.38640 H 0.00000 2.16744 -2.12252 H 0.00000 0.00000 -3.38020 H 0.00000 -2.16744 -2.12252 H 0.00000 -2.16503 0.38640 CH3C6H5 -270.9721786418 a.u. C 0.00624 0.92171 0.00304 C 1.21432 0.19501 0.00244 C 1.21337 -1.21330 -0.00039 C -0.00452 -1.91671 -0.00222 C -1.21851 -1.20285 -0.00036 C -1.20966 0.20331 0.00243 C 0.00166 2.43527 -0.00296 H 2.16657 0.73651 0.00530 H 2.16197 -1.75917 -0.00025 H -0.00897 -3.01074 -0.00418 H -2.17112 -1.74179 -0.00028 H -2.15895 0.75103 0.00513 H 1.02430 2.83392 0.07869 H -0.58938 2.83199 0.83833 H -0.44179 2.82362 -0.93468 NH2C6H5 -287.0139092440 a.u. C 0.00199 0.94354 0.00000 C -0.00248 0.22521 1.21565 C -0.00580 -1.18023 1.21343 C -0.00845 -1.89323 0.00000 C -0.00580 -1.18023 -1.21343 C -0.00248 0.22521 -1.21565 N -0.06784 2.35367 0.00000 H 0.32581 2.78138 -0.83394 H 0.32581 2.78138 0.83394 H -0.00684 0.77134 2.16552 H -0.00625 -1.71808 2.16653 H -0.01246 -2.98666 0.00000 H -0.00625 -1.71808 -2.16653 H -0.00684 0.77134 -2.16552 chloride anion -459.7807914518 a.u. nitrate anion -279.9885384225 a.u. N 0.00000 0.00000 0.00000 O -0.32835 1.22542 0.00000 O 1.22542 -0.32835 0.00000 O -0.89707 -0.89707 0.00000