Hydrogenation E-Iminium 1 M06-2X/def2-TZVP Geometry C -4.18935 0.58002 -0.55723 C -2.86361 0.97323 -0.60187 C -1.87746 0.17005 -0.02064 C -2.24826 -1.01384 0.63160 C -3.57676 -1.38961 0.68878 C -4.54685 -0.59703 0.08708 C -0.46779 0.55381 -0.07920 N 0.42119 -0.39343 -0.14018 C -0.05652 1.98053 -0.05209 C 1.85118 -0.27999 -0.06627 C 2.60869 -0.89506 -1.05207 C 3.99049 -0.81855 -0.97804 C 4.59562 -0.14242 0.07340 C 3.82305 0.45479 1.06046 C 2.44018 0.38485 0.99942 H -4.94602 1.19445 -1.02571 H -2.60263 1.88359 -1.12262 H -1.50809 -1.61174 1.15073 H -3.85882 -2.29169 1.21431 H -5.58676 -0.89351 0.12941 H 0.06494 -1.33752 -0.25941 H -0.72530 2.56646 -0.67893 H -0.17061 2.36193 0.96604 H 0.97140 2.12017 -0.37389 H 2.12469 -1.41436 -1.87004 H 4.59338 -1.28786 -1.74343 H 4.29663 0.96582 1.88766 H 1.82863 0.82153 1.77878 H 5.67457 -0.08800 0.12845 Hydrogenation E-Iminium 2 M06-2X/def2-TZVP Geometry C 3.85557 0.31827 0.24368 C 2.54668 0.77748 0.23746 C 1.49086 -0.05861 -0.14396 C 1.75904 -1.36817 -0.55757 C 3.06422 -1.82587 -0.57422 C 4.09651 -0.99312 -0.17016 C 0.11152 0.42327 -0.11811 C -0.21778 1.84008 -0.41863 N -0.82809 -0.43145 0.16328 C -2.25057 -0.23998 0.12407 C -2.98999 -0.61136 1.23760 C -4.36715 -0.45922 1.20718 C -4.98708 0.05002 0.07363 C -4.23426 0.40229 -1.03872 C -2.85622 0.25348 -1.02231 C 4.99033 1.19663 0.68427 H 2.35376 1.78764 0.57291 H 0.96643 -2.00702 -0.92840 H 3.27889 -2.82917 -0.91606 H 5.11547 -1.36166 -0.18416 H 0.52754 2.49292 0.02908 H -0.15763 1.99377 -1.49927 H -1.21056 2.11466 -0.07409 H -0.52111 -1.35463 0.45663 H -2.49482 -1.00209 2.11785 H -4.95488 -0.73854 2.07074 H -6.06236 0.16464 0.05379 H -4.71991 0.78225 -1.92704 H -2.26316 0.49623 -1.89463 H 5.46643 0.78666 1.57596 H 5.75158 1.25829 -0.09392 H 4.65092 2.20497 0.91236 Hydrogenation E-Iminium 3 M06-2X/def2-TZVP Geometry C 3.69034 1.02837 -0.00457 C 2.33910 1.27079 0.15662 C 1.42463 0.21312 0.15140 C 1.90928 -1.09715 0.01575 C 3.25879 -1.32842 -0.12336 C 4.17491 -0.27003 -0.14594 C 0.00296 0.49917 0.27388 C -0.46484 1.77029 0.89444 N -0.86295 -0.37036 -0.15959 C -2.29916 -0.28223 -0.13971 C -3.01014 -1.29547 0.48554 C -4.39545 -1.24057 0.48272 C -5.04997 -0.18840 -0.14378 C -4.32355 0.81121 -0.77684 C -2.93779 0.76697 -0.78348 H 1.99539 2.29148 0.25868 H 1.24480 -1.95154 0.07350 H 3.62146 -2.34547 -0.20551 H -1.48592 1.68333 1.25594 H 0.19938 2.04580 1.70972 H -0.43619 2.57168 0.15142 H -0.49080 -1.21407 -0.58298 H -2.48850 -2.10718 0.97686 H -4.96208 -2.02054 0.97249 H -6.13086 -0.15112 -0.14490 H -4.83451 1.62229 -1.27730 H -2.36147 1.52481 -1.29837 H 4.38261 1.86017 -0.01742 C 5.63829 -0.54580 -0.29980 H 5.82390 -1.12992 -1.20227 H 6.21596 0.37382 -0.35560 H 6.00303 -1.13202 0.54565 Hydrogenation E-Iminium 4 M06-2X/def2-TZVP Geometry C -3.32659 0.86124 -0.33484 C -1.98212 1.15885 -0.39713 C -1.00453 0.22376 -0.03080 C -1.43866 -1.03221 0.44664 C -2.76857 -1.33889 0.52221 C -3.73429 -0.39794 0.12043 C 0.39930 0.55314 -0.12688 C 0.85063 1.96820 -0.25858 N 1.28677 -0.40784 -0.11365 C 2.71681 -0.29925 -0.04113 C 3.47734 -0.95079 -1.00062 C 4.85976 -0.88262 -0.92048 C 5.46438 -0.17420 0.10922 C 4.68972 0.46300 1.06958 C 3.30675 0.39756 1.00371 H -1.69685 2.13692 -0.75732 H -0.73234 -1.76464 0.81878 H -3.10912 -2.29084 0.90527 H 0.31801 2.43434 -1.08660 H 0.59789 2.52386 0.64581 H 1.91644 2.04239 -0.44426 H 0.93349 -1.35690 -0.15525 H 2.99467 -1.49329 -1.80387 H 5.46342 -1.38227 -1.66564 H 6.54315 -0.12476 0.16808 H 5.16127 1.00166 1.88010 H 2.69182 0.86667 1.76149 H -4.05001 1.60240 -0.63902 O -4.99577 -0.78689 0.22217 C -6.03534 0.11409 -0.14637 H -6.96301 -0.42195 0.02286 H -6.00590 1.00829 0.47788 H -5.95169 0.38458 -1.19995 Hydrogenation E-Iminium 5 M06-2X/def2-TZVP Geometry C 2.19305 -0.90121 0.69032 C 0.83413 -0.64754 0.65359 C 0.34454 0.47235 -0.02705 C 1.23698 1.34117 -0.66114 C 2.59325 1.07436 -0.63863 C 3.06503 -0.04221 0.03764 C -1.09963 0.72681 -0.06401 N -1.89343 -0.29871 -0.12789 C -1.63386 2.11048 -0.01477 C -3.32807 -0.32498 -0.05788 C -4.01304 -1.03997 -1.02970 C -5.39600 -1.09724 -0.96546 C -6.07298 -0.45527 0.06358 C -5.37078 0.24087 1.03852 C -3.98735 0.30647 0.98703 C 4.54981 -0.33222 0.03174 F 4.90004 -1.09869 1.06103 F 4.89231 -0.96933 -1.08902 F 5.25729 0.79371 0.09087 H 2.57594 -1.75165 1.23799 H 0.16401 -1.29214 1.21011 H 0.88273 2.20726 -1.20231 H 3.28722 1.73722 -1.13843 H -1.45013 -1.20437 -0.25864 H -1.00443 2.76739 -0.61086 H -2.66419 2.16680 -0.35447 H -1.57490 2.47434 1.01491 H -3.47511 -1.53269 -1.83037 H -5.94360 -1.64349 -1.72123 H -5.89805 0.72510 1.84919 H -3.43004 0.82028 1.75975 H -7.15248 -0.50550 0.11097 Hydrogenation E-Iminium 6 M06-2X/def2-TZVP Geometry C 5.04803 0.41116 -0.68615 C 3.73717 0.85138 -0.73178 C 2.74154 0.15343 -0.04104 C 3.09027 -0.96972 0.72110 C 4.40527 -1.39211 0.77674 C 5.38335 -0.70700 0.06623 C 1.34342 0.57989 -0.10936 N 0.42468 -0.33966 -0.06820 C 0.97890 2.01619 -0.21027 C -0.99482 -0.18498 0.02149 C -1.79531 -0.93866 -0.82110 C -3.17408 -0.83359 -0.74576 C -3.75084 0.02769 0.19049 C -2.93054 0.76741 1.05295 C -1.56208 0.65924 0.97385 O -5.06454 0.20347 0.34514 C -5.95547 -0.52391 -0.48767 H 5.81123 0.94264 -1.23806 H 3.49234 1.71337 -1.33621 H 2.34535 -1.47958 1.32117 H 4.67113 -2.24690 1.38361 H 6.41208 -1.04002 0.10769 H 0.75555 -1.29981 -0.10594 H 1.06802 2.47774 0.77675 H 1.68594 2.52990 -0.85719 H -0.03422 2.15590 -0.57778 H -1.34687 -1.60337 -1.54978 H -3.78592 -1.42223 -1.41247 H -3.40028 1.40864 1.78608 H -0.93504 1.20948 1.66349 H -5.83649 -1.59862 -0.33542 H -6.95416 -0.22156 -0.18989 H -5.79403 -0.27428 -1.53835 Hydrogenation E-Iminium 7 M06-2X/def2-TZVP Geometry C -2.19313 -0.90729 -0.86394 C -3.57321 -0.84378 -0.76821 C -4.16132 -0.03536 0.20718 C -3.35060 0.69306 1.08819 C -1.98086 0.62579 0.98910 C -1.40297 -0.16514 -0.00175 N 0.01924 -0.27808 -0.11029 C 0.91224 0.66920 -0.12750 C 2.31989 0.28807 -0.06435 C 0.50051 2.09564 -0.19370 C 3.30395 1.05679 -0.69862 C 4.62883 0.67346 -0.65705 C 4.96838 -0.47118 0.04642 C 4.02606 -1.24340 0.70810 C 2.70299 -0.86060 0.64468 F 6.23761 -0.83291 0.10045 O -5.47712 0.09827 0.38345 C -6.35842 -0.62115 -0.46647 H -1.73576 -1.53001 -1.62353 H -4.17723 -1.42325 -1.44996 H -3.82879 1.29126 1.85161 H -1.35979 1.16587 1.69219 H 0.37379 -1.22727 -0.18177 H -0.52292 2.20917 -0.54052 H 0.59373 2.54295 0.79928 H 1.17544 2.64470 -0.84622 H 3.04023 1.94036 -1.26194 H 5.40186 1.24064 -1.15672 H 4.34367 -2.11043 1.27058 H 1.97213 -1.43023 1.20652 H -6.21076 -1.69722 -0.35435 H -7.36117 -0.35512 -0.14826 H -6.21479 -0.32954 -1.50893 Hydrogenation E-Iminium 8 M06-2X/def2-TZVP Geometry C -2.91557 -0.90199 0.66631 C -1.57252 -0.58847 0.62365 C -1.12145 0.54146 -0.07301 C -2.05801 1.36040 -0.71348 C -3.40153 1.04068 -0.69016 C -3.82708 -0.08936 -0.00052 C 0.30560 0.84851 -0.12219 C 0.79310 2.25102 -0.17815 N 1.14495 -0.14644 -0.10472 C 2.57048 -0.11807 0.00260 C 3.31023 -0.92855 -0.84323 C 4.69164 -0.95103 -0.75114 C 5.33277 -0.16058 0.20570 C 4.57214 0.63814 1.07061 C 3.20066 0.65641 0.97496 H -0.88112 -1.19897 1.19259 H -1.74622 2.23379 -1.26843 H -4.12040 1.66339 -1.20383 Br -5.65087 -0.51515 0.04676 H 1.81705 2.31124 -0.53685 H 0.14041 2.84364 -0.81424 H 0.73921 2.69049 0.82116 H 0.73740 -1.07384 -0.18215 H 2.81218 -1.53762 -1.58799 H 5.25583 -1.58120 -1.42180 O 6.65454 -0.10911 0.37894 H 5.08929 1.22142 1.81984 H 2.61827 1.24872 1.66858 C 7.48569 -0.90496 -0.45319 H 7.26250 -1.96549 -0.32176 H 7.36643 -0.62400 -1.50138 H 8.50350 -0.70434 -0.13527 H -3.26200 -1.76069 1.22381 Hydrogenation E-Iminium 9 M06-2X/def2-TZVP Geometry C -4.20500 0.79078 -0.41347 C -2.86856 1.12274 -0.48804 C -1.86856 0.24219 -0.05664 C -2.27040 -0.99143 0.49842 C -3.59252 -1.33041 0.58783 C -4.58081 -0.44579 0.12212 C -0.46998 0.60141 -0.15747 N 0.43540 -0.34072 -0.11339 C -0.04771 2.02183 -0.31742 C 1.85665 -0.20260 -0.00571 C 2.66725 -0.90079 -0.88356 C 4.04637 -0.80968 -0.77772 C 4.61151 -0.01408 0.22013 C 3.78106 0.67411 1.11376 C 2.41337 0.57553 1.00686 O 5.92553 0.14473 0.40661 C 6.82329 -0.53814 -0.45413 H -4.94606 1.48944 -0.77173 H -1.54497 -1.67515 0.92317 H -3.90887 -2.26432 1.03184 H 0.09648 -1.29588 -0.13690 H 1.00967 2.10919 -0.54468 H -0.62034 2.47691 -1.12405 H -0.27092 2.58060 0.59331 H 2.22712 -1.51141 -1.66264 H 4.66594 -1.35724 -1.47185 H 4.24191 1.26612 1.89259 H 1.77339 1.08560 1.71616 H 6.69547 -1.61933 -0.36824 H 6.67987 -0.22608 -1.49085 H 7.81980 -0.26144 -0.12518 H -2.60913 2.08249 -0.91174 O -5.83325 -0.86162 0.24589 C -6.89334 -0.01377 -0.18259 H -7.80831 -0.55912 0.02345 H -6.81564 0.18668 -1.25241 H -6.88715 0.92165 0.37929 Hydrogenation E-Iminium 10 M06-2X/def2-TZVP Geometry C -3.71353 0.62915 0.02954 C -2.38506 0.96995 0.13726 C -1.38152 -0.02269 0.13722 C -1.75422 -1.36348 0.06276 C -3.08745 -1.72157 -0.02491 C -4.07751 -0.74450 -0.05421 C 0.00710 0.37689 0.22865 N 0.94453 -0.43478 -0.18061 C 0.37777 1.70478 0.79656 C 2.36481 -0.23315 -0.17341 C 3.16996 -1.18414 0.42843 C 4.54829 -1.03462 0.42077 C 5.11881 0.07661 -0.20121 C 4.29503 1.02342 -0.82212 C 2.92771 0.86713 -0.81480 O 6.43276 0.31698 -0.26287 C 7.32265 -0.60992 0.33842 O -5.37603 -0.98081 -0.14519 O -4.73599 1.48824 -0.00558 C -4.45280 2.87215 0.09018 C -5.82585 -2.32514 -0.25252 H -2.11032 2.01292 0.18732 H -1.02220 -2.15837 0.13653 H -3.35638 -2.76683 -0.05492 H 0.63740 -1.31629 -0.57592 H 1.40176 1.70639 1.16118 H 0.29344 2.47419 0.02446 H -0.30523 1.96112 1.60264 H 2.72542 -2.04208 0.91797 H 5.16245 -1.78213 0.89995 H 4.76056 1.86566 -1.31530 H 2.29601 1.58568 -1.32126 H 7.23165 -1.59322 -0.12785 H 8.32041 -0.21716 0.17031 H 7.13568 -0.68742 1.41167 H -3.83097 3.20071 -0.74638 H -5.41274 3.37697 0.04824 H -3.95879 3.10356 1.03729 H -6.90619 -2.26787 -0.33503 H -5.41130 -2.79814 -1.14473 H -5.55335 -2.89481 0.63765 Hydrogenation E-Iminium 11 M06-2X/def2-TZVP Geometry C 2.54588 -1.01240 -0.25400 C 1.18257 -0.84701 -0.34253 C 0.60789 0.42589 -0.20780 C 1.45310 1.52114 0.00653 C 2.81678 1.34634 0.11305 C 3.39357 0.07891 -0.01612 C -0.82927 0.63866 -0.27700 N -1.63831 -0.35869 -0.05947 C -1.37998 1.98415 -0.60499 C -3.07280 -0.35810 -0.05362 C -3.74386 -1.28438 -0.84805 C -5.11892 -1.32084 -0.83289 C -5.84094 -0.43936 -0.01802 C -5.15980 0.47247 0.78950 C -3.77393 0.50395 0.77092 O -7.17136 -0.54975 -0.07648 C -7.96252 0.31196 0.72654 H 2.97451 -1.99363 -0.40834 H 1.04011 2.51372 0.12787 H 3.44731 2.19981 0.32344 H -1.20916 -1.25166 0.15862 H -2.39006 1.90925 -0.99969 H -1.41310 2.60166 0.29633 H -0.73261 2.47781 -1.32548 H -3.18803 -1.96168 -1.48486 H -5.66855 -2.02206 -1.44563 H -5.69442 1.14703 1.44128 H -3.24372 1.19093 1.41835 H -8.99497 0.05868 0.50793 H -7.76094 0.14676 1.78702 H -7.77956 1.35768 0.47006 H 0.57835 -1.71406 -0.58428 C 7.61224 -0.45702 0.25552 C 6.75500 -1.42915 0.75356 C 5.38384 -1.25859 0.66060 C 4.85229 -0.10604 0.07946 C 5.72293 0.86849 -0.41202 C 7.09371 0.68997 -0.33002 H 8.68345 -0.59391 0.32306 H 7.15612 -2.31992 1.21829 H 4.72182 -2.01044 1.07202 H 5.32639 1.75468 -0.89157 H 7.75949 1.44408 -0.72802 Hydrogenation E-Iminium 12 M06-2X/def2-TZVP Geometry C -3.11141 -1.82529 -0.08905 C -1.81189 -1.45045 0.04980 C -1.47308 -0.07434 0.20288 C -2.47784 0.87132 0.21933 C -3.82799 0.50794 0.05527 C -4.15623 -0.86426 -0.10211 C -0.09041 0.36755 0.31209 N 0.85950 -0.41393 -0.11560 C 0.24606 1.68778 0.91744 C 2.27360 -0.18179 -0.13709 C 3.11055 -1.16097 0.37073 C 4.48468 -0.98606 0.33865 C 5.01983 0.17765 -0.21648 C 4.16384 1.15064 -0.74793 C 2.80022 0.97069 -0.71509 O 6.32614 0.44606 -0.29460 C 7.24977 -0.50437 0.21336 C -4.86073 1.47628 0.05044 C -6.16215 1.09070 -0.10033 C -6.48725 -0.27457 -0.25278 C -5.50896 -1.23191 -0.25310 H -3.36722 -2.87371 -0.17824 H -1.05428 -2.22287 0.10513 H -2.24504 1.92309 0.33209 H 0.56753 -1.30169 -0.51042 H -0.44222 1.90220 1.73092 H 1.26961 1.70079 1.28370 H 0.14416 2.47895 0.17053 H 2.69427 -2.06083 0.80721 H 5.12441 -1.75438 0.74570 H 4.60161 2.03287 -1.19430 H 2.14522 1.71011 -1.15734 H 8.23471 -0.07904 0.04942 H 7.09311 -0.66421 1.28227 H 7.16508 -1.45214 -0.32248 H -4.60414 2.52175 0.16972 H -6.95189 1.83000 -0.10310 H -7.52362 -0.56265 -0.37082 H -5.76050 -2.27847 -0.37021 Hydrogenation E-Iminium 13 M06-2X/def2-TZVP Geometry C -4.95118 -0.63532 -0.39205 S -3.35641 -1.19218 -0.51864 C -2.73112 0.29817 0.09279 C -3.75958 1.18173 0.36299 C -5.02677 0.64491 0.08746 C -1.33039 0.54706 0.26833 C -0.86776 1.90048 0.69035 N -0.46412 -0.41115 0.06741 C 0.96485 -0.33554 0.08242 C 1.67072 -1.28266 0.82221 C 3.04519 -1.25332 0.82679 C 3.73447 -0.28294 0.08680 C 3.02005 0.65078 -0.66647 C 1.63462 0.61411 -0.67032 H -3.60812 2.18032 0.74532 H -0.86953 2.57667 -0.16703 H -1.55157 2.30352 1.43333 H 0.13633 1.86144 1.10318 H -0.83409 -1.33614 -0.13130 H 1.14084 -2.02965 1.40047 H 3.61965 -1.97034 1.39671 O 5.06668 -0.33626 0.15610 H 3.52995 1.39278 -1.26212 H 1.08163 1.31557 -1.28190 C 5.82778 0.60915 -0.57955 H 5.60455 1.62614 -0.25077 H 6.86792 0.37939 -0.37279 H 5.63657 0.51161 -1.65006 H -5.95712 1.17259 0.23132 H -5.76440 -1.28041 -0.68724 Hydrogenation E-Iminium 14 M06-2X/def2-TZVP Geometry O -2.10506 -0.66526 0.12930 C -1.74955 0.62816 -0.13699 C -2.84560 1.42264 -0.31384 C -0.35507 0.92072 -0.17897 C 0.10666 2.30822 -0.45209 N 0.47651 -0.06761 0.01316 C 1.90084 -0.04097 0.07125 C 2.59950 -1.04758 -0.57733 C 3.98281 -1.07815 -0.53067 C 4.67139 -0.09443 0.18258 C 3.95516 0.90376 0.85554 C 2.58086 0.92866 0.80681 H -2.84329 2.47832 -0.53168 H -0.60736 2.81178 -1.09866 H 0.17473 2.87277 0.47979 H 1.08795 2.30200 -0.92232 H 0.04780 -0.98252 0.12966 H 2.06491 -1.80656 -1.13565 H 4.51150 -1.86404 -1.04847 O 6.00082 -0.03106 0.29080 H 4.50797 1.63770 1.42541 H 2.03703 1.67855 1.36488 C 6.78630 -1.02229 -0.35353 H 6.62804 -1.00046 -1.43361 H 7.81906 -0.77429 -0.13139 H 6.55506 -2.01476 0.03833 C -3.46471 -0.69684 0.12180 C -3.97902 0.57817 -0.14724 C -5.36880 0.76463 -0.19900 C -6.16967 -0.33067 0.02070 C -5.61859 -1.59873 0.28882 C -4.25485 -1.81087 0.34539 H -5.79172 1.73838 -0.40508 H -7.24510 -0.22437 -0.01123 H -6.28622 -2.43339 0.45635 H -3.82805 -2.78181 0.55144 Hydrogenation E-Iminium 15 M06-2X/def2-TZVP Geometry C -4.95859 -0.02005 -0.78145 C -3.65524 0.42576 -0.90755 C -2.64608 -0.12667 -0.11243 C -2.97586 -1.10417 0.83428 C -4.28328 -1.53550 0.96457 C -5.27373 -1.00015 0.15092 C -1.25897 0.31968 -0.25862 C -0.94935 1.71828 -0.67061 C -1.42141 2.74718 0.36516 N -0.31446 -0.54181 -0.01735 C 1.10188 -0.33915 0.04185 C 1.92345 -1.22227 -0.63780 C 3.29953 -1.07150 -0.58476 C 3.85192 -0.03103 0.16481 C 3.01064 0.84209 0.86693 C 1.64544 0.68635 0.81216 O 5.16098 0.20371 0.28097 C 6.07094 -0.65126 -0.39463 H -5.73097 0.39832 -1.41231 H -3.42571 1.18330 -1.64436 H -2.22488 -1.48866 1.51472 H -4.53263 -2.27790 1.71058 H -6.29611 -1.33963 0.25251 H -1.47845 1.89214 -1.61070 H 0.11270 1.82336 -0.87672 H -1.17843 3.74784 0.01377 H -2.49802 2.68617 0.51756 H -0.93397 2.59664 1.32809 H -0.61774 -1.49816 0.14513 H 1.49366 -2.02461 -1.22554 H 3.92724 -1.76225 -1.12731 H 3.46231 1.62480 1.46087 H 1.00108 1.34299 1.38251 H 5.97819 -1.67744 -0.03324 H 5.90589 -0.61761 -1.47350 H 7.06161 -0.27185 -0.16536 Hydrogenation E-Iminium 16 M06-2X/def2-TZVP Geometry C -4.21038 1.20025 -0.53116 C -2.86192 1.39776 -0.66748 C -1.93863 0.43340 -0.21863 C -2.44128 -0.71497 0.41200 C -3.79387 -0.92130 0.56713 C -4.69664 0.03533 0.08243 C -0.51488 0.63664 -0.38142 C 0.04487 2.00034 -0.59838 N 0.28574 -0.39578 -0.34757 H -2.52239 2.30289 -1.15007 H -1.77052 -1.44440 0.85070 H -4.14326 -1.80523 1.07890 O -6.01492 -0.06704 0.17362 H 1.10146 1.97491 -0.84198 H -0.49548 2.48022 -1.41322 H -0.11045 2.60932 0.29390 H -0.15254 -1.31004 -0.33508 H -4.92550 1.92808 -0.88855 C -6.58487 -1.22198 0.77937 H -7.65941 -1.08543 0.72073 H -6.29697 -2.12263 0.23493 H -6.27972 -1.29755 1.82421 C 3.76181 -1.24781 -1.29008 C 2.38206 -1.16983 -1.28823 C 1.72139 -0.40934 -0.31642 C 2.38779 0.27514 0.68454 H 4.30030 -1.82371 -2.02913 H 1.80696 -1.68670 -2.04544 H 1.84086 0.82331 1.44122 C 4.42444 -0.54728 -0.29755 C 3.77883 0.21104 0.68953 C 4.83122 0.74533 1.51153 C 5.97659 0.28639 0.97178 O 5.75928 -0.49647 -0.12129 H 4.74270 1.37810 2.37748 H 7.00986 0.42281 1.24205 Hydrogenation E-Iminium 17 M06-2X/def2-TZVP Geometry C 3.62828 0.26133 0.25103 C 2.20976 -0.19838 0.40622 N 1.25001 0.51260 -0.08354 C 1.94062 -1.47209 1.12245 C -0.15785 0.23473 -0.09949 C -1.02810 1.23965 0.28735 C -2.39506 1.01859 0.26610 C -2.88797 -0.21712 -0.15985 C -1.99656 -1.21623 -0.57291 C -0.63964 -0.99255 -0.54726 O -4.18256 -0.53313 -0.21824 C -5.14232 0.43461 0.18107 C 3.78972 1.63919 -0.37580 C 4.40676 -0.80766 -0.53865 H 4.03117 0.27895 1.27009 H 1.51893 1.39399 -0.51365 H 2.70526 -1.62625 1.88220 H 0.94849 -1.48022 1.56984 H 2.00497 -2.30954 0.42312 H -0.64475 2.19617 0.62224 H -3.06232 1.80713 0.57955 H -2.40241 -2.15506 -0.92398 H 0.04098 -1.75626 -0.89978 H -6.11103 -0.03823 0.05590 H -5.00070 0.70999 1.22818 H -5.08338 1.32253 -0.45156 H 3.26329 2.41800 0.18015 H 4.84417 1.90932 -0.37758 H 3.45978 1.64899 -1.41819 H 4.39370 -1.77713 -0.04329 H 3.99419 -0.91860 -1.54288 H 5.44432 -0.49151 -0.63112 Hydrogenation E-Iminium 18 M06-2X/def2-TZVP Geometry C -1.13859 0.48793 0.58205 C -0.75787 1.78899 1.19094 N -0.24793 -0.31201 0.09712 C 1.17100 -0.13165 -0.00631 C 1.99072 -1.17710 0.38413 C 3.36620 -1.05797 0.27705 C 3.91935 0.11606 -0.23892 C 3.07773 1.15701 -0.65210 C 1.71197 1.03418 -0.54185 O 5.22794 0.33182 -0.38716 C 6.13755 -0.68750 0.00014 H -2.94822 0.20271 1.55895 H -0.78829 2.57501 0.43211 H 0.24813 1.75835 1.60587 H -1.48224 2.05275 1.95959 H -0.59307 -1.20182 -0.25332 H 1.56139 -2.08708 0.78625 H 3.99300 -1.87815 0.59269 H 3.52712 2.04648 -1.07172 H 1.06866 1.82815 -0.89703 H 7.12841 -0.29513 -0.20506 H 5.97354 -1.59531 -0.58408 H 6.04305 -0.90584 1.06589 C -4.36317 -1.60899 0.05936 C -2.86267 -1.31728 0.04037 C -2.58233 0.10273 0.52851 C -3.35231 1.13936 -0.32550 C -4.84730 0.82693 -0.32411 C -5.12723 -0.59789 -0.78833 H -4.72241 -1.57196 1.09225 H -4.53832 -2.62306 -0.30000 H -2.50737 -1.42892 -0.99230 H -2.33758 -2.04955 0.66179 H -3.18122 2.14756 0.05472 H -2.96427 1.10265 -1.34920 H -5.23875 0.96503 0.68857 H -5.36122 1.54648 -0.96227 H -4.82990 -0.70463 -1.83658 H -6.19681 -0.80307 -0.74229 Hydrogenation E-Iminium 19 M06-2X/def2-TZVP Geometry C -3.01290 -2.12842 -1.07698 C -3.34883 -0.78927 -0.93365 C -3.12192 -0.12380 0.27218 C -2.56116 -0.82922 1.33130 C -2.23623 -2.17404 1.19545 C -2.45452 -2.82419 -0.01056 C -3.41289 1.34926 0.39299 C -2.47687 2.19835 -0.51009 C -1.05232 1.97233 -0.12883 C -0.42038 2.85729 0.87839 N -0.44456 0.95303 -0.63565 C 0.88715 0.48225 -0.40937 C 1.05640 -0.88456 -0.19812 C 2.32118 -1.38402 0.00232 C 3.43131 -0.52852 -0.02045 C 3.25208 0.83529 -0.25911 C 1.97473 1.33613 -0.45797 O 4.61658 -1.10883 0.18339 C 5.78540 -0.30362 0.16048 H -3.20512 -2.63462 -2.01403 H -3.81250 -0.26276 -1.76206 H -2.38931 -0.32954 2.27814 H -1.81544 -2.71239 2.03497 H -2.20643 -3.87195 -0.11748 H -3.31406 1.66947 1.43142 H -4.43512 1.57154 0.08363 H -2.71468 3.25589 -0.39775 H -2.63585 1.92042 -1.55280 H -0.05549 3.76382 0.38639 H 0.41019 2.37776 1.39111 H -1.18294 3.17240 1.59139 H -1.01387 0.34637 -1.22682 H 0.19194 -1.53980 -0.17840 H 2.48849 -2.43792 0.17712 H 4.09528 1.50762 -0.30761 H 1.84038 2.38718 -0.67854 H 6.61398 -0.97681 0.35552 H 5.91496 0.16358 -0.81793 H 5.74358 0.46175 0.93841 Hydrogenation E-Iminium 20 M06-2X/def2-TZVP Geometry C 4.99672 0.80949 -0.06677 C 3.54824 1.06854 -0.29855 C 2.58430 0.14044 -0.16083 C 2.90665 -1.29256 0.20096 C 4.38937 -1.60919 0.00999 C 5.25553 -0.52116 0.62947 C 1.19396 0.54484 -0.30545 C 0.79750 1.88194 -0.83581 N 0.27319 -0.31197 0.03913 H 2.31979 -1.97340 -0.42422 H 4.60558 -1.68198 -1.05917 H 1.45368 2.16055 -1.65638 H -0.23133 1.87138 -1.18500 H 0.88782 2.64206 -0.05730 H 0.59932 -1.22566 0.33755 H 5.41592 1.64798 0.49441 C -3.08522 1.06783 0.79766 C -1.71608 0.94763 0.74321 C -1.14749 -0.13957 0.08309 C -1.94867 -1.11461 -0.48710 H -3.55488 1.89705 1.30838 H -1.08801 1.68138 1.23144 H -1.49989 -1.96360 -0.98835 C -3.90560 0.09914 0.20499 C -3.32832 -0.99956 -0.43477 C -6.10933 -0.64630 -0.25245 O -5.22072 0.30577 0.31200 H -7.10926 -0.27876 -0.04626 H 2.62282 -1.48388 1.24263 H 5.49520 0.84053 -1.04410 H 4.60993 -2.58155 0.44832 H 5.02046 -0.42804 1.69315 H 6.31095 -0.77954 0.55751 H 3.28261 2.08155 -0.57830 H -3.93974 -1.76310 -0.89130 H -5.97507 -1.62479 0.21291 H -5.96179 -0.72195 -1.33162 Hydrogenation Z-Iminium 1 M06-2X/def2-TZVP Geometry C -1.53104 2.87100 0.02583 C -0.74921 1.60390 -0.04462 N 0.54692 1.70150 -0.07487 C -1.45195 0.32519 -0.09475 C 1.54073 0.66814 0.06091 C 2.58279 0.62813 -0.85141 C 3.55516 -0.35172 -0.71032 C 3.47924 -1.26230 0.33421 C 2.43632 -1.19369 1.25010 C 1.45864 -0.22171 1.12123 C -2.66345 0.18350 0.59050 C -3.36308 -1.00797 0.51986 C -2.88508 -2.04580 -0.26909 C -1.70172 -1.89759 -0.98423 C -0.97681 -0.72569 -0.88978 H -0.90634 3.74763 -0.13514 H -2.34385 2.85207 -0.69824 H -1.97876 2.95215 1.01976 H 0.92338 2.64238 -0.14169 H 2.62889 1.34091 -1.66579 H 4.37184 -0.39958 -1.41764 H 2.38891 -1.89239 2.07421 H 0.64593 -0.15293 1.83259 H -3.04906 0.99057 1.19925 H -4.28661 -1.12287 1.07058 H -1.34531 -2.69868 -1.61730 H -0.06081 -0.61607 -1.45454 H 4.24143 -2.02217 0.44252 H -3.44132 -2.97181 -0.33523 Hydrogenation Z-Iminium 2 M06-2X/def2-TZVP Geometry C 3.18216 -0.63976 0.15870 C 2.35254 0.45854 0.32166 C 1.06458 0.48270 -0.22939 C 0.61541 -0.59795 -0.99543 C 1.45199 -1.68155 -1.19008 C 2.71159 -1.70596 -0.60965 C 0.25810 1.68808 -0.07679 C 0.92758 3.01982 -0.00935 N -1.04099 1.67921 -0.01065 C -1.95214 0.57386 0.13099 C -3.03999 0.51614 -0.72522 C -3.94934 -0.52151 -0.58272 C -3.76602 -1.47390 0.40989 C -2.67759 -1.38988 1.26997 C -1.76149 -0.35909 1.13914 C 4.55119 -0.68815 0.77267 H 2.70974 1.29805 0.90502 H -0.35933 -0.58017 -1.46265 H 1.12227 -2.51132 -1.80054 H 3.35273 -2.56658 -0.76285 H 1.41954 3.11881 0.96154 H 1.69575 3.09567 -0.77678 H 0.21703 3.83797 -0.11143 H -1.49053 2.58971 -0.01088 H -3.17029 1.26389 -1.49801 H -4.80130 -0.58088 -1.24610 H -4.47977 -2.27880 0.52212 H -2.54609 -2.12388 2.05332 H -0.91466 -0.27869 1.80828 H 4.62328 -1.51157 1.48445 H 5.30968 -0.85106 0.00625 H 4.78745 0.23605 1.29642 Hydrogenation Z-Iminium 3 M06-2X/def2-TZVP Geometry C 1.82593 -1.30735 -0.80433 C 0.82020 -0.36808 -0.75990 C 1.01595 0.83961 -0.07041 C 2.24786 1.06927 0.55451 C 3.23353 0.10212 0.53343 C 3.04306 -1.10028 -0.14600 C 0.01632 1.89351 -0.06823 C 0.44710 3.32220 -0.01511 N -1.26660 1.67098 -0.12124 C -1.99154 0.43688 0.03011 C -2.96053 0.12365 -0.90931 C -3.68908 -1.04695 -0.75355 C -3.44710 -1.87709 0.33188 C -2.48198 -1.53763 1.27288 C -1.74812 -0.37181 1.13028 H -0.10283 -0.55485 -1.29092 H 2.43303 1.99686 1.07955 H 4.17182 0.28578 1.04062 H 0.80668 3.54423 0.99272 H -0.37366 4.00224 -0.23476 H 1.26909 3.49734 -0.70612 H -1.85566 2.49153 -0.22058 H -3.13602 0.77730 -1.75483 H -4.44585 -1.30645 -1.48103 H -4.01908 -2.78716 0.45174 H -2.30741 -2.17691 2.12748 H -0.99971 -0.09168 1.86012 H 1.67435 -2.22281 -1.36252 C 4.10716 -2.15288 -0.17675 H 4.25071 -2.52842 -1.18999 H 5.05643 -1.77397 0.19526 H 3.81165 -3.00091 0.44490 Hydrogenation Z-Iminium 4 M06-2X/def2-TZVP Geometry C 1.55848 -1.08434 -0.79291 C 0.47274 -0.25721 -0.71679 C 0.57250 1.00827 -0.09594 C 1.81770 1.39336 0.42429 C 2.90919 0.55405 0.38469 C 2.78796 -0.69951 -0.22794 C -0.52081 1.94607 -0.05075 C -0.24519 3.41399 0.04435 N -1.78370 1.60481 -0.09400 C -2.38871 0.30763 0.04566 C -3.30044 -0.10483 -0.91263 C -3.91186 -1.34209 -0.76691 C -3.61096 -2.14194 0.32641 C -2.70472 -1.70540 1.28575 C -2.08973 -0.47139 1.15374 H -0.45253 -0.57303 -1.17645 H 1.93509 2.36056 0.89427 H 3.84496 0.87452 0.81677 H 0.08157 3.65040 1.05972 H -1.13660 4.00309 -0.16210 H 0.54838 3.70244 -0.64102 H -2.44615 2.36915 -0.16527 H -3.52038 0.52557 -1.76523 H -4.62308 -1.67781 -1.50909 H -4.09066 -3.10487 0.43778 H -2.48408 -2.32282 2.14582 H -1.38738 -0.11573 1.89652 H 1.50196 -2.04323 -1.28918 O 3.77263 -1.57864 -0.33384 C 5.05354 -1.25964 0.20007 H 5.68064 -2.12072 -0.00475 H 4.99005 -1.09663 1.27693 H 5.46498 -0.37751 -0.29256 Hydrogenation Z-Iminium 5 M06-2X/def2-TZVP Geometry C 1.36566 3.53781 -0.10858 C 1.39163 2.04897 -0.08986 N 2.54827 1.46345 -0.13693 C 0.12849 1.30743 -0.04874 C 2.87743 0.07093 0.03139 C 3.72034 -0.51604 -0.89899 C 4.06589 -1.84942 -0.73696 C 3.57788 -2.56702 0.34617 C 2.74882 -1.95474 1.27856 C 2.39369 -0.62434 1.12899 C -0.94039 1.82133 0.68630 C -2.15727 1.15840 0.69980 C -2.31313 0.00922 -0.05583 C -1.26595 -0.49186 -0.82257 C -0.04272 0.14429 -0.81047 C -3.63013 -0.73333 -0.08041 F -4.54258 -0.15156 0.69136 F -4.11153 -0.78982 -1.32233 F -3.46636 -1.98715 0.34479 H 0.65853 3.88784 -0.85988 H 1.01326 3.89793 0.86111 H 2.34987 3.96441 -0.29221 H 3.35214 2.07164 -0.26640 H 4.09053 0.05393 -1.74262 H 4.71845 -2.32363 -1.45727 H 2.38602 -2.51119 2.13216 H 1.75791 -0.13288 1.85403 H -0.82770 2.72552 1.26935 H -2.98117 1.53964 1.28688 H -1.41372 -1.37951 -1.42448 H 0.76796 -0.24527 -1.41122 H 3.85273 -3.60566 0.47174 Hydrogenation Z-Iminium 6 M06-2X/def2-TZVP Geometry C 2.84308 2.59725 0.04742 C 1.81072 1.52382 -0.02809 N 0.56555 1.89520 -0.05317 C 2.23228 0.12641 -0.09252 C -0.63270 1.11681 0.07064 C -1.69394 1.40538 -0.76797 C -2.88046 0.69655 -0.65557 C -2.99691 -0.29959 0.31450 C -1.91809 -0.56744 1.17032 C -0.74421 0.13713 1.05487 O -4.09112 -1.03795 0.51244 C -5.23116 -0.80206 -0.30005 C 3.38913 -0.26805 0.58687 C 3.83472 -1.57505 0.49613 C 3.15723 -2.48303 -0.30588 C 2.02720 -2.08784 -1.01378 C 1.55376 -0.79488 -0.90009 H 3.62263 2.42062 -0.69208 H 2.41393 3.58787 -0.09146 H 3.31381 2.56781 1.03328 H 0.40683 2.89637 -0.11496 H -1.59948 2.17699 -1.52295 H -3.70014 0.92897 -1.31853 H -2.04228 -1.32714 1.92980 H 0.07987 -0.06351 1.72704 H -5.98851 -1.50027 0.04164 H -5.59191 0.22076 -0.17357 H -5.00427 -0.99191 -1.35118 H 3.93167 0.43560 1.20413 H 4.71633 -1.88101 1.04263 H 3.51572 -3.50072 -0.38845 H 1.51522 -2.79135 -1.65609 H 0.67673 -0.49428 -1.45741 Hydrogenation Z-Iminium 7 M06-2X/def2-TZVP Geometry C 1.18878 0.41079 -0.94750 C 2.30226 -0.41245 -0.92812 C 3.25555 -0.26767 0.08362 C 3.08215 0.71593 1.06562 C 1.97425 1.53276 1.04162 C 1.02259 1.36565 0.04028 N -0.11726 2.23757 0.02023 C -1.38027 1.94971 -0.10357 C -1.90826 0.59469 -0.01412 C -2.31525 3.09053 -0.33292 C -3.07290 0.27119 -0.72247 C -3.63185 -0.98689 -0.62439 C -3.03912 -1.90566 0.22581 C -1.90816 -1.60780 0.97298 C -1.33668 -0.36134 0.83982 F -3.57545 -3.10788 0.33890 O 4.36051 -1.00934 0.18936 C 4.61184 -2.00632 -0.78962 H 0.45309 0.30511 -1.73476 H 2.42631 -1.14867 -1.70805 H 3.83772 0.81912 1.83220 H 1.84065 2.28996 1.80484 H 0.10889 3.22720 0.04944 H -3.19081 2.99863 0.30716 H -1.83188 4.05104 -0.16384 H -2.65790 3.06663 -1.37058 H -3.53841 0.99765 -1.37495 H -4.51678 -1.26372 -1.18013 H -1.50115 -2.35145 1.64390 H -0.46049 -0.12074 1.42559 H 4.71276 -1.55899 -1.78059 H 5.54856 -2.47391 -0.50374 H 3.81563 -2.75379 -0.79533 Hydrogenation Z-Iminium 8 M06-2X/def2-TZVP Geometry C -1.59846 -0.55662 -0.78857 C -0.59514 0.38874 -0.76354 C -0.76664 1.58512 -0.05287 C -1.97247 1.81150 0.62062 C -2.96533 0.85125 0.62886 C -2.77456 -0.33014 -0.07797 C 0.23922 2.63960 -0.08297 C -0.19239 4.06793 -0.05005 N 1.51792 2.40873 -0.15192 C 2.24164 1.18131 0.01167 C 3.26196 0.89003 -0.87517 C 3.99856 -0.27582 -0.72641 C 3.70854 -1.14347 0.32733 C 2.68389 -0.82354 1.23096 C 1.95687 0.33225 1.07922 H 0.31230 0.20602 -1.32246 H -2.13540 2.73258 1.16411 H -3.88586 1.01724 1.17006 Br -4.12279 -1.63188 -0.08690 H -1.02525 4.22843 -0.73201 H -0.53753 4.31085 0.95817 H 0.62410 4.74456 -0.29537 H 2.10561 3.22691 -0.27976 H 3.48244 1.56278 -1.69531 H 4.78980 -0.49393 -1.42750 O 4.35352 -2.28794 0.56328 H 2.49514 -1.49976 2.05333 H 1.17593 0.58202 1.78565 C 5.41715 -2.66297 -0.29926 H 5.78857 -3.60910 0.08052 H 5.05851 -2.79353 -1.32220 H 6.21552 -1.91875 -0.27479 H -1.47678 -1.46915 -1.35471 Hydrogenation Z-Iminium 9 M06-2X/def2-TZVP Geometry C -1.38292 3.59164 0.04469 C -0.70405 2.26103 -0.04880 N 0.60303 2.28959 -0.09000 C -1.49284 1.05297 -0.09509 C 1.55098 1.22311 0.05059 C 2.58600 1.12309 -0.85999 C 3.53293 0.11707 -0.72810 C 3.43626 -0.78548 0.33036 C 2.39016 -0.66178 1.25578 C 1.45663 0.33856 1.12230 O 4.29275 -1.78834 0.54994 C 5.38687 -1.95379 -0.33802 C -2.79648 1.07556 0.42054 C -3.61403 -0.03328 0.37343 C -3.14834 -1.20136 -0.24071 C -1.85861 -1.22834 -0.79985 C -1.04408 -0.13287 -0.71728 H -2.22268 3.64446 -0.64468 H -1.76883 3.72741 1.05777 H -0.69265 4.40835 -0.15855 H 1.01826 3.21186 -0.16233 H 2.65564 1.82081 -1.68584 H 4.33396 0.04971 -1.44861 H 2.34813 -1.35976 2.08065 H 0.65556 0.43841 1.84359 H 5.03636 -2.15173 -1.35333 H 6.02928 -1.07080 -0.33101 H 5.94204 -2.81116 0.02905 H -4.60393 0.01554 0.80120 H -1.53575 -2.13336 -1.29587 H -0.06380 -0.17982 -1.16925 H -3.17957 1.97108 0.89125 C -5.16877 -2.37309 0.17842 H -5.15477 -2.20547 1.25664 H -5.80931 -1.63706 -0.31015 H -5.53209 -3.37341 -0.03277 O -3.84967 -2.32046 -0.35336 Hydrogenation Z-Iminium 10 M06-2X/def2-TZVP Geometry C -1.21107 3.93904 -0.03053 C -0.55271 2.59792 0.06366 N 0.75130 2.61124 0.19029 C -1.34728 1.39602 0.01479 C 1.68730 1.53076 0.06738 C 2.61135 1.31487 1.08408 C 3.51645 0.28151 0.97176 C 3.50970 -0.54219 -0.15992 C 2.58740 -0.30657 -1.18213 C 1.68201 0.73587 -1.06482 O 4.42119 -1.52168 -0.17618 C 4.48474 -2.37205 -1.30967 C -0.92110 0.18063 0.60162 C -1.71504 -0.93709 0.55380 C -2.97543 -0.87816 -0.11158 C -3.39862 0.32045 -0.67582 C -2.60088 1.44814 -0.59569 O -3.66122 -2.00805 -0.12419 O -1.40918 -2.12432 1.08890 C -4.93457 -2.03363 -0.75711 C -0.16227 -2.25133 1.74775 H -2.10863 3.97302 0.58214 H -0.53463 4.73662 0.27166 H -1.49995 4.12484 -1.06773 H 1.17214 3.52501 0.31689 H 2.61246 1.94558 1.96473 H 4.24721 0.09027 1.74562 H 2.57589 -0.91604 -2.07341 H 0.96556 0.92095 -1.85521 H 5.28238 -3.07986 -1.10771 H 3.54369 -2.90977 -1.44578 H 4.72087 -1.80144 -2.21031 H 0.02020 0.13285 1.12449 H -4.35427 0.37985 -1.17425 H -2.95962 2.36520 -1.04197 H -5.30105 -3.04808 -0.64058 H -5.61884 -1.33546 -0.27193 H -4.84043 -1.79319 -1.81761 H -0.09872 -3.28541 2.07140 H 0.66327 -2.02472 1.06625 H -0.11282 -1.59167 2.61774 Hydrogenation Z-Iminium 11 M06-2X/def2-TZVP Geometry C -0.93201 4.20451 -0.19417 C -1.09776 2.71930 -0.17248 N -2.32217 2.27168 -0.22307 C 0.07536 1.86709 -0.11102 C -2.82708 0.94640 -0.00957 C -3.73990 0.42959 -0.91015 C -4.26548 -0.83979 -0.71549 C -3.87270 -1.58365 0.39715 C -2.95982 -1.03842 1.31192 C -2.44287 0.21969 1.11477 O -4.31404 -2.81282 0.67987 C -5.25152 -3.41879 -0.19630 C 1.25039 2.36696 0.46850 C 2.39846 1.60485 0.49853 C 2.43370 0.33359 -0.08456 C 1.26746 -0.14605 -0.69579 C 0.10606 0.59302 -0.70007 H -0.13245 4.48976 -0.87466 H -1.85406 4.70926 -0.47697 H -0.65702 4.54652 0.80666 H -3.03901 2.97334 -0.37575 H -4.03726 1.00667 -1.77762 H -4.97431 -1.23353 -1.42842 H -2.68715 -1.62614 2.17775 H -1.74367 0.64091 1.82574 H -4.82909 -3.53424 -1.19673 H -5.46265 -4.39663 0.22485 H -6.17207 -2.83342 -0.24425 H 3.29525 2.01193 0.94589 H 1.27064 -1.12718 -1.15140 H -0.77248 0.18862 -1.18266 H 1.26655 3.35463 0.90994 C 6.00120 -1.99858 -0.03481 C 5.68912 -1.18234 1.04412 C 4.53318 -0.41977 1.02632 C 3.66662 -0.47296 -0.06725 C 3.98757 -1.30108 -1.14461 C 5.14993 -2.05360 -1.13026 H 6.90670 -2.59066 -0.02239 H 6.34497 -1.14438 1.90367 H 4.28517 0.19490 1.88277 H 3.34376 -1.33017 -2.01473 H 5.39623 -2.67915 -1.97787 Hydrogenation Z-Iminium 12 M06-2X/def2-TZVP Geometry C -0.90074 3.64024 -0.01671 C -0.26161 2.29285 -0.10774 N 1.04101 2.26298 -0.08699 C -1.09146 1.10488 -0.23432 C 1.94355 1.16160 0.06274 C 3.10150 1.15786 -0.69417 C 4.02644 0.13583 -0.54631 C 3.78461 -0.88134 0.37743 C 2.61428 -0.85614 1.14976 C 1.70059 0.15962 1.00013 O 4.60867 -1.90788 0.60430 C 5.83313 -1.96930 -0.11077 C -0.67404 -0.02168 -1.00307 C -1.50922 -1.08350 -1.15824 C -2.78896 -1.11416 -0.54347 C -3.20994 0.00577 0.22145 C -2.34729 1.11173 0.33862 C -3.66098 -2.21465 -0.67887 C -4.89050 -2.19880 -0.07809 C -5.30866 -1.08632 0.68462 C -4.48727 -0.00585 0.83240 H -0.17278 4.44126 -0.13294 H -1.68358 3.74115 -0.76579 H -1.36396 3.75082 0.96671 H 1.49872 3.16846 -0.11345 H 3.28566 1.94723 -1.41333 H 4.92375 0.14473 -1.14638 H 2.46068 -1.64313 1.87520 H 0.80623 0.18246 1.60911 H 6.44970 -1.09390 0.10368 H 6.33707 -2.86485 0.23848 H 5.65247 -2.04596 -1.18497 H 0.28892 -0.01713 -1.49391 H -1.20521 -1.92657 -1.76619 H -2.68945 1.96417 0.91285 H -3.34493 -3.06869 -1.26477 H -5.55481 -3.04619 -0.18632 H -6.28514 -1.09600 1.14998 H -4.80034 0.85247 1.41429 Hydrogenation Z-Iminium 13 M06-2X/def2-TZVP Geometry C 2.16034 2.52564 0.05749 S 1.00105 1.30092 0.05666 C 2.22619 0.07790 -0.04628 C 3.48746 0.66363 -0.07545 C 3.45013 2.05742 -0.01578 C 2.02442 -1.33309 -0.10091 C 3.21700 -2.23442 -0.20399 N 0.85493 -1.91665 -0.06852 C -0.43150 -1.28168 0.04070 C -1.12912 -0.95093 -1.10681 C -2.36381 -0.32742 -1.00791 C -2.89614 -0.04694 0.25234 C -2.18355 -0.40105 1.40603 C -0.95881 -1.01979 1.30233 H 4.40480 0.09665 -0.13762 H 3.86757 -2.08850 0.65786 H 2.91948 -3.27974 -0.24352 H 3.78555 -1.99760 -1.10265 H 0.85671 -2.92926 -0.11855 H -0.70706 -1.16698 -2.08032 H -2.90037 -0.07149 -1.90902 O -4.07433 0.54857 0.45751 H -2.62267 -0.18255 2.36964 H -0.40392 -1.29216 2.19134 C -4.86099 0.91146 -0.66661 H -5.12384 0.03091 -1.25610 H -5.76211 1.36390 -0.26565 H -4.33412 1.63541 -1.29161 H 4.32109 2.69434 -0.02541 H 1.84235 3.55606 0.11366 Hydrogenation Z-Iminium 14 M06-2X/def2-TZVP Geometry O 2.65184 1.10503 -0.06759 C 1.28029 1.03757 -0.03904 C 0.85944 -0.27143 0.00800 C 0.64115 2.30967 -0.07926 C 1.49712 3.52769 -0.16274 N -0.65586 2.46478 -0.04973 C -1.63918 1.42116 0.05469 C -2.20739 0.90093 -1.09269 C -3.13557 -0.12704 -0.99885 C -3.49074 -0.62378 0.25655 C -2.91016 -0.08084 1.41092 C -1.99110 0.93968 1.31191 H -0.15848 -0.62154 0.03866 H 2.16485 3.56100 0.69861 H 2.12803 3.46943 -1.04977 H 0.89787 4.43436 -0.19650 H -0.99676 3.41856 -0.09430 H -1.92242 1.28667 -2.06340 H -3.57608 -0.52492 -1.90061 O -4.37354 -1.60756 0.45727 H -3.20980 -0.47545 2.37206 H -1.53957 1.36036 2.20158 C -5.02546 -2.17812 -0.66663 H -4.30327 -2.64657 -1.33858 H -5.69656 -2.93304 -0.27009 H -5.60070 -1.42277 -1.20568 C 3.10371 -0.16528 -0.03729 C 2.03156 -1.06696 0.00906 C 2.28846 -2.44947 0.04693 C 3.59890 -2.85405 0.03627 C 4.65584 -1.91841 -0.01091 C 4.43452 -0.55851 -0.04841 H 1.47766 -3.16411 0.08426 H 3.83727 -3.90821 0.06495 H 5.67403 -2.28439 -0.01745 H 5.24018 0.16042 -0.08413 Hydrogenation Z-Iminium 15 M06-2X/def2-TZVP Geometry C -3.28774 -2.34614 -0.55091 C -3.05619 -0.98509 -0.66173 C -2.03913 -0.38846 0.08657 C -1.28263 -1.16243 0.97363 C -1.54395 -2.51317 1.10306 C -2.53689 -3.10819 0.33329 C -1.82579 1.05997 0.01501 C -3.01573 1.96835 -0.01743 C -2.73575 3.46211 0.00073 N -0.64251 1.59026 0.02405 C 0.64352 0.96481 -0.09513 C 1.66482 1.39515 0.73163 C 2.92635 0.82750 0.62967 C 3.15780 -0.16876 -0.31937 C 2.11783 -0.57763 -1.16660 C 0.86899 -0.01459 -1.05979 O 4.33102 -0.78054 -0.50230 C 5.43069 -0.40355 0.31211 H -4.06048 -2.80947 -1.14909 H -3.64998 -0.40035 -1.35155 H -0.50813 -0.70385 1.57455 H -0.97147 -3.10522 1.80408 H -2.72890 -4.16892 0.42803 H -3.65344 1.67249 0.81997 H -3.58506 1.69917 -0.91266 H -2.21542 3.76817 0.91084 H -2.15895 3.78192 -0.86931 H -3.67716 4.00661 -0.02297 H -0.61252 2.60430 0.08167 H 1.48279 2.16578 1.47150 H 3.71305 1.16797 1.28572 H 2.32766 -1.33402 -1.91044 H 0.07238 -0.32591 -1.72259 H 5.21706 -0.59685 1.36546 H 6.26466 -1.01922 -0.00911 H 5.67617 0.65057 0.16728 Hydrogenation Z-Iminium 16 M06-2X/def2-TZVP Geometry C -3.72584 0.04392 0.29398 C -2.88551 1.13493 0.34028 C -1.56076 1.06482 -0.11608 C -1.11397 -0.15203 -0.67819 C -1.94998 -1.23071 -0.76116 C -3.26207 -1.15509 -0.26068 C -0.74387 2.25261 -0.06946 C -1.38889 3.60296 -0.04026 N 0.56417 2.24518 -0.05383 H -3.26669 2.05409 0.76455 H -0.11708 -0.23558 -1.08582 H -1.62804 -2.15876 -1.21284 O -3.98570 -2.26000 -0.36702 H -0.66885 4.39469 -0.23788 H -1.80900 3.77644 0.95323 H -2.19919 3.65930 -0.76340 H 1.01100 3.15237 -0.12662 H -4.73163 0.12825 0.67651 C -5.32890 -2.26147 0.10434 H -5.92666 -1.52850 -0.43942 H -5.35983 -2.05476 1.17517 H -5.70765 -3.25960 -0.08810 C 2.17454 -0.68700 1.55111 C 1.30600 0.35722 1.30232 C 1.47163 1.14986 0.16046 C 2.49634 0.96124 -0.74735 H 2.07758 -1.31380 2.42617 H 0.49499 0.56868 1.98623 H 2.59434 1.59864 -1.61710 C 3.19201 -0.88357 0.63216 C 3.38240 -0.08753 -0.50534 C 4.54295 -0.62700 -1.16101 C 4.94012 -1.66108 -0.39479 O 4.14115 -1.83798 0.69430 H 5.01043 -0.28889 -2.06948 H 5.75640 -2.35740 -0.48476 Hydrogenation Z-Iminium 17 M06-2X/def2-TZVP Geometry C -3.61466 1.38098 -0.46305 C -2.37421 0.60464 -0.19513 N -1.24292 1.13238 -0.53286 C -2.46573 -0.72775 0.47414 C 0.09201 0.61911 -0.38133 C 1.04117 1.44414 0.19678 C 2.34657 1.00423 0.34205 C 2.69938 -0.26994 -0.10754 C 1.73411 -1.08424 -0.71429 C 0.43922 -0.64231 -0.85683 O 3.92381 -0.79146 -0.01369 C 4.95339 -0.01681 0.58343 C -3.02806 -1.76649 -0.51199 C -3.34832 -0.63940 1.72527 H -4.37727 0.73275 -0.89475 H -4.00828 1.74775 0.48810 H -3.44183 2.22672 -1.12569 H -1.28870 2.05796 -0.95179 H -1.46214 -1.02963 0.77176 H 0.76585 2.43104 0.54916 H 3.07475 1.65563 0.80131 H 2.03709 -2.05674 -1.07714 H -0.29335 -1.26440 -1.35318 H 5.12662 0.90027 0.01666 H 4.70490 0.22414 1.61907 H 5.84448 -0.63553 0.55727 H -2.46575 -1.80764 -1.44454 H -2.98319 -2.74866 -0.04322 H -4.07147 -1.55759 -0.74922 H -2.99363 0.12195 2.42048 H -4.38721 -0.42934 1.46963 H -3.32016 -1.60058 2.23659 Hydrogenation Z-Iminium 18 M06-2X/def2-TZVP Geometry C -1.46865 1.58326 -0.13941 C -2.51151 2.64118 -0.21276 N -0.23079 1.94310 -0.25722 C 0.94923 1.11734 -0.23024 C 1.92062 1.37552 0.71967 C 3.07711 0.61137 0.75049 C 3.25703 -0.40984 -0.18440 C 2.27271 -0.64628 -1.15257 C 1.12719 0.11554 -1.17958 O 4.33060 -1.20218 -0.23905 C 5.37278 -1.00533 0.70487 H -0.95858 -0.40525 0.32807 H -2.11868 3.58955 -0.57393 H -2.93248 2.78479 0.78536 H -3.32795 2.31657 -0.85786 H -0.05714 2.93682 -0.38342 H 1.77807 2.16367 1.44889 H 3.82488 0.81753 1.50144 H 2.44218 -1.42798 -1.88025 H 0.38063 -0.05160 -1.94477 H 5.80600 -0.00841 0.60109 H 6.12473 -1.75469 0.47922 H 5.00567 -1.15020 1.72301 C -2.82358 -1.91167 -0.93266 C -2.49401 -0.44098 -1.17947 C -1.85816 0.16715 0.09224 C -2.84048 0.04200 1.27329 C -3.16621 -1.42988 1.51604 C -3.75301 -2.07889 0.26586 H -1.89365 -2.46204 -0.75755 H -3.27669 -2.33264 -1.83078 H -3.41253 0.10237 -1.41998 H -1.82406 -0.33625 -2.03466 H -2.41191 0.49424 2.17066 H -3.76373 0.58017 1.03952 H -2.25433 -1.95762 1.81185 H -3.86255 -1.51073 2.35117 H -4.72036 -1.61853 0.04043 H -3.94305 -3.13688 0.44706 Hydrogenation Z-Iminium 19 M06-2X/def2-TZVP Geometry C 0.97048 -2.82466 0.57971 C 1.27395 -1.67875 1.30031 C 2.20720 -0.76485 0.81921 C 2.83108 -1.01923 -0.40011 C 2.52748 -2.16361 -1.12680 C 1.59488 -3.06847 -0.63674 C 2.52066 0.48499 1.59858 C 1.53933 1.64828 1.29081 C 1.61800 2.03934 -0.14086 C 2.81208 2.77614 -0.62972 N 0.68031 1.74981 -0.97640 C -0.57484 1.09229 -0.68702 C -1.61899 1.82490 -0.15412 C -2.83066 1.20199 0.10608 C -2.98321 -0.15583 -0.18152 C -1.91511 -0.87710 -0.72796 C -0.71219 -0.25750 -0.98352 O -4.10640 -0.84956 0.03212 C -5.23080 -0.17555 0.57438 H 0.25373 -3.53362 0.97348 H 0.78997 -1.49939 2.25406 H 3.58839 -0.33636 -0.77277 H 3.03242 -2.35822 -2.06404 H 1.36800 -3.96824 -1.19330 H 3.54674 0.80397 1.41129 H 2.44064 0.29308 2.66855 H 1.82209 2.51646 1.89064 H 0.52583 1.34961 1.55150 H 2.79743 3.77811 -0.19223 H 2.83894 2.86181 -1.71426 H 3.72198 2.29070 -0.27784 H 0.83381 2.00915 -1.94797 H -1.49487 2.87972 0.05853 H -3.64202 1.77924 0.52323 H -2.05633 -1.92858 -0.93813 H 0.12161 -0.81714 -1.39069 H -5.00078 0.23198 1.56133 H -5.56216 0.62441 -0.09117 H -6.01251 -0.92322 0.66334 Hydrogenation Z-Iminium 20 M06-2X/def2-TZVP Geometry C 3.89012 -1.42830 0.56887 C 3.28882 -0.06705 0.52829 C 2.10383 0.22628 -0.04086 C 1.30475 -0.83355 -0.77779 C 2.20997 -1.99124 -1.19191 C 2.97052 -2.51399 0.02035 C 1.68444 1.62091 -0.03728 C 2.68631 2.72937 0.05200 N 0.43741 1.98476 -0.15404 H 0.82767 -0.38392 -1.65127 H 2.91698 -1.65664 -1.95631 H 3.06675 2.78798 1.07423 H 3.52800 2.54530 -0.61102 H 2.23732 3.69186 -0.18658 H 0.27231 2.97945 -0.26993 H 4.20900 -1.64320 1.59235 C -2.07074 -0.29177 1.32907 C -0.91503 0.43420 1.15922 C -0.74699 1.19387 0.00484 C -1.73987 1.25340 -0.95646 H -2.23505 -0.88704 2.21668 H -0.14176 0.42076 1.91762 H -1.60319 1.85678 -1.84560 C -3.07636 -0.25804 0.35340 C -2.90636 0.52326 -0.79185 C -5.22775 -0.98886 -0.32572 O -4.16040 -0.99483 0.61007 H -5.98957 -1.64158 0.08782 H 0.49850 -1.21967 -0.15223 H 4.82019 -1.37736 -0.01167 H 1.60288 -2.77882 -1.63688 H 2.25557 -2.81411 0.79086 H 3.55380 -3.39810 -0.23293 H 3.87042 0.71985 0.99636 H -3.67135 0.57076 -1.55199 H -5.63269 0.01802 -0.44469 H -4.89834 -1.37589 -1.29207 Knölker’s Complex M06/def2-TZVP Geometry C -0.74862 1.19362 -0.57827 C 0.65756 1.11321 -0.67906 C 1.51357 2.33301 -0.79817 C 0.76073 3.57315 -0.34037 C -0.60885 3.64350 -0.99382 C -1.49492 2.49353 -0.53661 C -1.29359 -0.13996 -0.57957 C -0.16775 -0.98628 -0.75483 C 1.04212 -0.26627 -0.77473 H 2.45018 2.22313 -0.24334 H 0.63756 3.54846 0.75130 H -1.09466 4.59723 -0.77392 H -1.85051 2.69553 0.48351 O -0.17513 -2.33950 -0.80691 Si 2.70334 -1.09870 -0.94558 Si -3.09973 -0.57360 -0.44882 Fe -0.12129 0.43220 1.38896 C -0.29990 -1.47698 2.14686 O -0.56499 -2.45477 2.64451 H -1.08341 -2.66017 -0.82236 H 1.80962 2.45993 -1.84912 H 1.34362 4.46858 -0.56961 H -0.48253 3.59732 -2.08272 H -2.39185 2.43369 -1.16243 C -4.02606 -0.05344 -1.98799 H -5.08175 -0.32665 -1.90895 H -3.97370 1.02576 -2.14696 H -3.61699 -0.54019 -2.87607 C -3.85870 0.24514 1.04781 H -3.77582 1.33319 1.00124 H -4.92010 -0.00776 1.11930 H -3.36906 -0.07695 1.97056 C -3.31320 -2.43311 -0.26034 H -3.02340 -2.99403 -1.15517 H -2.78005 -2.83960 0.60367 H -4.37450 -2.64423 -0.10383 C 2.75493 -2.03847 -2.56000 H 1.94413 -2.76815 -2.60497 H 2.64966 -1.36342 -3.41211 C 4.10757 0.14003 -0.92498 H 4.02035 0.87904 -1.72411 H 4.18264 0.67377 0.02559 H 5.04925 -0.39632 -1.07203 C 2.96407 -2.29972 0.46802 H 3.06039 -1.77886 1.42466 H 2.12841 -2.99897 0.54446 H 3.87772 -2.88050 0.31547 H 3.70242 -2.57308 -2.66711 C 1.79730 0.86618 2.14177 O 2.71326 1.33800 2.60066 H -0.83730 1.29557 2.62323 Cartesian coordinates of reaction components relevant to chiral phosphate catalysis Reaction components required for re-creating the statistical model have been published elsewhere. Iminium 1 M06/def2-TZVP Geometry C 1.45125 -1.28476 0.44582 N 0.76445 -0.24882 0.12385 C 1.69908 0.88501 -0.29408 C 3.07950 0.33267 -0.12413 C 2.90748 -1.10958 0.32060 C -0.65855 -0.14720 0.07066 C -1.27674 0.99556 0.55459 C -2.65635 1.06289 0.51792 C -3.39529 0.01333 -0.00342 C -2.76109 -1.11680 -0.49563 C -1.38400 -1.20321 -0.46368 O 1.28539 1.91548 -0.65907 H 0.95982 -2.19267 0.78448 H 3.61720 0.44399 -1.06686 H 3.60816 0.94870 0.60632 H 3.39079 -1.34847 1.27270 H 3.30161 -1.84081 -0.39328 H -0.69541 1.81023 0.96505 H -3.15660 1.94348 0.90012 H -4.47573 0.07963 -0.03499 H -3.34004 -1.92782 -0.91860 H -0.87587 -2.06575 -0.88124 Iminium 2 M06/def2-TZVP Geometry C 1.06221 1.10187 -0.00009 N 1.20495 -0.16846 -0.00005 C 2.65721 -0.54540 -0.00012 C 3.40541 0.75278 0.00007 C 2.33934 1.83826 -0.00007 C 0.15878 -1.21854 -0.00003 O 2.98693 -1.67094 0.00015 H 0.07001 1.54869 -0.00011 H 4.05863 0.78194 0.87398 H 4.05894 0.78199 -0.87359 H 2.37551 2.50197 -0.86963 H 2.37540 2.50208 0.86942 H 0.36285 -1.83678 -0.87808 H 0.36288 -1.83678 0.87802 C -3.73032 0.52186 0.00003 C -3.10415 0.23071 1.20111 C -1.84776 -0.34908 1.20187 C -1.21348 -0.64134 -0.00001 C -1.84781 -0.34910 -1.20186 C -3.10420 0.23069 -1.20107 H -4.71729 0.96814 0.00004 H -3.60108 0.44449 2.13933 H -1.36299 -0.59483 2.14226 H -1.36307 -0.59486 -2.14227 H -3.60116 0.44446 -2.13928 Iminium 3 M06/def2-TZVP Geometry C -2.98771 -1.27772 0.43053 N -2.27896 -0.24972 0.12584 C -3.19243 0.90420 -0.28968 C -4.58269 0.37400 -0.13502 C -4.43920 -1.07684 0.29099 C -0.85793 -0.17078 0.08154 C -0.21922 0.96800 0.55189 C 1.15881 1.01854 0.52785 C 1.88285 -0.05415 0.02619 C 1.23664 -1.18510 -0.45605 C -0.13942 -1.24380 -0.43014 O -2.75858 1.93035 -0.64319 H -2.51684 -2.19737 0.76612 H -5.10405 0.98925 0.60146 H -5.11316 0.50854 -1.07881 H -4.83724 -1.79029 -0.43867 H -4.93834 -1.32107 1.23349 H -0.78461 1.80063 0.94815 H 1.67652 1.89326 0.90002 Br 3.75202 0.02853 -0.01579 H 1.81210 -2.00670 -0.86276 H -0.65182 -2.10747 -0.84005 Iminium 4 M06/def2-TZVP Geometry C 3.56705 -1.27641 0.42629 N 2.85558 -0.24881 0.12459 C 3.76609 0.90739 -0.28827 C 5.15779 0.38114 -0.13278 C 5.01812 -1.07192 0.28681 C 1.43495 -0.17324 0.08061 C 0.79302 0.96447 0.54889 C -0.58556 1.00904 0.52746 C -1.31542 -0.06495 0.03040 C -0.65854 -1.19364 -0.44992 C 0.71796 -1.24950 -0.42651 O 3.33095 1.93309 -0.64194 H 3.09831 -2.19773 0.75986 H 5.69043 0.52189 -1.07437 H 5.67486 0.99476 0.60812 H 5.51884 -1.31889 1.22770 H 5.41751 -1.78056 -0.44679 H 1.35618 1.80008 0.94229 H -1.09669 1.88731 0.90164 I -3.39013 0.02098 -0.01098 H -1.22399 -2.02312 -0.85612 H 1.23205 -2.11295 -0.83519 Iminium 5 M06/def2-TZVP Geometry C -1.09673 -3.46509 -1.38565 C -1.76513 -4.42904 -2.02475 C -1.82308 -2.52170 -0.60129 N -1.30838 -1.54577 0.06912 S -2.42736 -0.49027 1.08981 C 0.08370 -1.19823 0.06308 C -2.03775 1.06155 0.44498 O -3.70829 -0.94472 0.68350 O -1.91225 -0.66133 2.39648 C -1.07344 1.83604 1.08127 C -0.73386 3.05102 0.52689 C -1.33562 3.50205 -0.64712 C -2.29838 2.69970 -1.26202 C -2.65745 1.48248 -0.72763 C -0.98512 4.83224 -1.21562 C 0.86110 -1.46200 1.17523 C 2.18649 -1.05947 1.17137 C 2.70603 -0.40260 0.07074 C 1.91446 -0.14741 -1.04130 C 0.59372 -0.54213 -1.04887 C 4.13923 0.06425 0.03947 F 4.79068 -0.25142 1.14651 F 4.78378 -0.47592 -0.98973 F 4.19100 1.38637 -0.10745 H -0.01635 -3.38931 -1.43524 H -1.25530 -5.17554 -2.62109 H -2.84650 -4.50189 -1.96908 H -2.90742 -2.61603 -0.53212 H -0.61025 1.48855 1.99675 H 0.01128 3.67040 1.01334 H -2.77732 3.04820 -2.17020 H -3.41800 0.86935 -1.19690 H -1.11333 4.85460 -2.29794 H -1.63971 5.60230 -0.79711 H 0.03968 5.11553 -0.97531 H 0.43401 -1.96588 2.03326 H 2.81394 -1.25916 2.03028 H 2.33634 0.36609 -1.89752 H -0.04854 -0.33534 -1.89843 Iminium 6 M06/def2-TZVP Geometry C 3.28793 -0.62485 -1.46482 C 4.09943 -1.43686 -2.14722 C 2.27991 -1.19294 -0.63092 N 1.42979 -0.52833 0.07768 S 0.25304 -1.46157 1.13879 C 1.30814 0.90303 0.06901 C -1.24317 -0.91099 0.47573 O 0.53587 -2.80694 0.78651 O 0.48785 -0.92289 2.42577 C -1.88891 0.17229 1.06013 C -3.06077 0.62478 0.49202 C -3.59218 0.01984 -0.64531 C -2.91582 -1.06234 -1.21120 C -1.74576 -1.53562 -0.66154 C -4.87730 0.49381 -1.22867 C 0.69676 1.50572 -1.02015 C 0.53558 2.87859 -1.01908 C 0.97612 3.62653 0.06159 C 1.58305 3.00827 1.14265 C 1.75214 1.63467 1.15708 H 3.38087 0.45398 -1.51694 H 4.88636 -1.05130 -2.78347 H 4.00157 -2.51611 -2.08938 H 2.20713 -2.27836 -0.55529 H -1.47712 0.64062 1.94600 H -3.58146 1.46378 0.93963 H -3.32740 -1.54269 -2.09192 H -1.23245 -2.38807 -1.09083 H -4.89215 0.38034 -2.31310 H -5.70905 -0.09627 -0.83312 H -5.07307 1.53683 -0.98064 H 0.34369 0.89745 -1.84686 H 0.06216 3.36484 -1.86284 H 1.93016 3.59728 1.98231 H 2.21636 1.13439 1.99786 H 0.84654 4.70181 0.06021 Iminium 7 M06/def2-TZVP Geometry C -3.14849 -0.89922 -1.05430 C -3.98800 -1.79703 -1.57733 C -1.97908 -1.35645 -0.37930 N -1.08672 -0.60155 0.17046 S 0.29912 -1.40196 1.06745 C -1.08488 0.83419 0.10724 C 1.63818 -0.72275 0.20008 O 0.19563 -0.86372 2.37149 O 0.10421 -2.77456 0.76598 C 2.24974 0.42049 0.69917 C 3.28821 0.97655 -0.02278 C 3.69196 0.39728 -1.21583 C 3.07232 -0.74696 -1.69883 C 2.03446 -1.31947 -0.99138 C -1.40753 1.57105 1.23385 C -1.35142 2.95199 1.15745 C -0.97366 3.57229 -0.02234 C -0.65298 2.81893 -1.14091 C -0.70397 1.43891 -1.08137 H -3.33764 0.16642 -1.11628 H -4.89541 -1.49782 -2.08711 H -3.79307 -2.86251 -1.51015 H -1.80540 -2.42945 -0.29141 H 1.91940 0.85257 1.63584 H 3.78764 1.86187 0.34970 H 3.40822 -1.19903 -2.62346 H 1.54989 -2.22379 -1.34006 H -1.69220 1.07014 2.15083 H -1.60678 3.54507 2.02663 H -0.35893 3.30656 -2.06190 H -0.44040 0.82803 -1.93885 H -0.93048 4.65335 -0.07160 H 4.50860 0.83822 -1.77482 Iminium 8 M06/def2-TZVP Geometry C 3.30342 -1.21212 -0.28546 C 4.21032 -2.15543 -0.56467 C 1.93295 -1.60867 -0.15822 N 0.92195 -0.82910 0.07011 C -0.39496 -1.52449 0.36105 C 1.03254 0.60335 0.19137 C -1.62474 -0.81740 -0.00966 O -0.31001 -2.59228 0.87305 C -2.77634 -1.16884 0.69857 C -3.98692 -0.58988 0.36562 C -4.05479 0.31451 -0.68756 C -2.91420 0.64399 -1.41033 C -1.69405 0.08857 -1.06899 C 0.57395 1.20147 1.35452 C 0.66931 2.57920 1.47802 C 1.20759 3.33681 0.44646 C 1.65511 2.72211 -0.71636 C 1.56774 1.34573 -0.85191 H 3.58137 -0.17934 -0.12847 H 5.26298 -1.91747 -0.64412 H 3.92348 -3.18891 -0.72183 H 1.69035 -2.66589 -0.21776 H -2.70510 -1.89051 1.50165 H -4.87889 -0.84810 0.91961 H -2.97786 1.33367 -2.24063 H -0.81347 0.34304 -1.64208 H 0.15469 0.60045 2.15202 H 0.32182 3.05921 2.38249 H 2.06534 3.31434 -1.52292 H 1.88940 0.85500 -1.76284 H 1.27497 4.41162 0.54666 H -5.00425 0.76134 -0.95182 Iminium 9 M06/def2-TZVP Geometry C -1.45053 -2.05597 0.00005 C -2.47072 -2.92323 0.00006 C -1.73773 -0.66701 0.00002 N -0.86053 0.29154 0.00000 C -1.40142 1.71011 -0.00003 C 0.55998 0.02767 0.00000 O -2.57397 1.84085 -0.00001 C 1.21962 -0.09538 1.21003 C 2.58124 -0.34457 1.20246 C 3.25857 -0.46684 0.00001 C 2.58123 -0.34463 -1.20244 C 1.21962 -0.09544 -1.21002 H -0.41865 -2.38828 0.00005 H -2.30728 -3.99407 0.00008 H -3.50211 -2.58525 0.00005 H -2.77521 -0.33058 0.00001 H 0.67333 0.00298 2.14210 H 3.11290 -0.44503 2.14038 H 3.11288 -0.44514 -2.14037 H 0.67332 0.00287 -2.14209 H 4.32395 -0.66082 0.00001 C -0.35962 2.75840 -0.00009 H -0.84749 3.72940 -0.00012 H 0.28423 2.66388 0.87686 H 0.28419 2.66381 -0.87706 Iminium 10 M06/def2-TZVP Geometry C -1.56243 2.46456 0.00399 C -1.79150 3.78030 0.09037 C -0.21888 2.00805 -0.04512 N 0.17037 0.77069 -0.11327 C 1.68088 0.54771 -0.21805 C -0.76864 -0.32449 -0.10369 O 2.34017 1.50460 -0.42525 C -1.40053 -0.66602 1.07980 C -2.30347 -1.71486 1.07677 C -2.56417 -2.40293 -0.09677 C -1.92762 -2.04567 -1.27481 C -1.02198 -0.99991 -1.28534 H -2.37336 1.74675 -0.04011 H -2.79693 4.18234 0.11697 H -0.97671 4.49564 0.13798 H 0.59165 2.73733 -0.04670 H -1.18448 -0.11649 1.99017 H -2.80359 -1.99430 1.99560 H -2.13838 -2.58078 -2.19221 H -0.51722 -0.70714 -2.19972 H -3.27051 -3.22378 -0.09414 C 2.14423 -0.84612 0.03975 C 3.49832 -1.07482 -0.60395 C 2.21463 -1.02194 1.56107 H 1.40854 -1.54986 -0.35833 H 3.82431 -2.09687 -0.41063 H 3.46809 -0.92353 -1.68332 H 4.24325 -0.39461 -0.18862 H 2.56003 -2.03116 1.78550 H 2.92964 -0.31564 1.98867 H 1.24875 -0.88270 2.04967 Iminium 11 M06/def2-TZVP Geometry C -1.48730 2.65095 0.07790 C -1.57145 3.97958 0.19343 C -0.21065 2.05424 -0.12450 N 0.03861 0.78753 -0.22607 C 1.48720 0.41468 -0.57774 C -0.97088 -0.23336 -0.14341 O 1.95995 1.04270 -1.45724 C -1.21307 -0.99533 -1.27395 C -2.14862 -2.01121 -1.20507 C -2.82182 -2.25659 -0.01871 C -2.57451 -1.47983 1.10203 C -1.64456 -0.45718 1.04597 H -2.36754 2.01975 0.11317 H -2.52282 4.47990 0.32486 H -0.68860 4.60984 0.15944 H 0.65174 2.71146 -0.23020 H -0.67229 -0.79366 -2.19264 H -2.35190 -2.61331 -2.08168 H -3.10401 -1.67285 2.02657 H -1.42965 0.15008 1.91892 H -3.54764 -3.05866 0.03247 C 2.16432 -0.60967 0.30487 C 3.64524 -0.58251 -0.05925 C 1.98403 -0.18812 1.76363 C 1.62866 -2.02826 0.08863 H 4.17863 -1.28217 0.58578 H 3.80706 -0.87956 -1.09598 H 4.07706 0.40979 0.07906 H 2.57459 -0.85622 2.39302 H 2.34457 0.82985 1.93617 H 0.94747 -0.25829 2.09755 H 2.28024 -2.71389 0.63409 H 0.61459 -2.16858 0.46250 H 1.65910 -2.31204 -0.96563 Iminium 12 M06/def2-TZVP Geometry C 0.78467 -1.72217 0.35769 C 1.49381 -0.97169 1.29198 C 2.79120 -0.61687 1.00055 C 3.39479 -1.00304 -0.19713 C 2.66517 -1.77084 -1.10198 C 1.36024 -2.13001 -0.83954 C 4.79986 -0.60189 -0.48316 S -0.87303 -2.09548 0.66073 O -1.36206 -3.11005 -0.20379 O -1.18686 -2.02322 2.03865 N -1.67891 -0.58257 -0.01612 C -2.56522 -0.72303 -0.94286 C -1.28531 0.67618 0.55467 C -1.78669 1.02144 1.77903 C -1.35436 2.20385 2.39579 C -0.42555 2.99223 1.77999 C 0.10374 2.65477 0.51716 C -0.33471 1.47007 -0.13389 C -3.31603 0.33808 -1.53012 C -4.20887 0.05405 -2.48137 C 1.06754 3.46453 -0.11889 C 1.57427 3.12479 -1.33886 C 1.13304 1.95662 -1.98283 C 0.20042 1.14821 -1.39787 H 1.02916 -0.67897 2.22611 H 3.35992 -0.03254 1.71581 H 3.13380 -2.09312 -2.02484 H 0.79409 -2.73041 -1.54167 H 4.90906 0.48423 -0.43429 H 5.47971 -1.01989 0.26313 H 5.12795 -0.93687 -1.46618 H -2.73677 -1.74542 -1.28175 H -2.49936 0.37049 2.27081 H -1.75721 2.47760 3.36232 H -0.07808 3.90225 2.25689 H -3.14729 1.35170 -1.18382 H -4.80499 0.82636 -2.95127 H -4.37268 -0.96430 -2.81879 H 1.39489 4.36792 0.38391 H 2.31190 3.75639 -1.81822 H 1.53532 1.69674 -2.95474 H -0.11933 0.24805 -1.91124 Iminium 13 M06/def2-TZVP Geometry C -1.19010 -1.15846 -0.49413 C -1.77944 -0.15916 -1.26051 C -2.97170 0.38423 -0.83092 C -3.58538 -0.05745 0.34012 C -2.96788 -1.06171 1.08628 C -1.77223 -1.61421 0.68345 C -4.89618 0.50501 0.76879 S 0.32988 -1.81698 -0.98936 O 0.61179 -3.05068 -0.34616 O 0.58078 -1.57506 -2.36096 N 1.47733 -0.65894 -0.15128 C 2.28973 -1.13132 0.73336 C 1.34690 0.72736 -0.48424 C 1.78126 1.18991 -1.71383 C 1.56923 2.51141 -2.05745 C 0.91435 3.34678 -1.16872 C 0.47718 2.88858 0.06317 C 0.69065 1.56590 0.42628 C 3.26610 -0.37409 1.44371 C 4.05375 -0.99344 2.32562 O 0.31862 1.01074 1.58905 C -0.49095 1.76750 2.46898 H -1.31145 0.17494 -2.17890 H -3.44725 1.16069 -1.41971 H -3.44371 -1.41732 1.99353 H -1.29884 -2.40100 1.25825 H -5.71425 -0.09394 0.35840 H -5.00427 0.49326 1.85380 H -5.03399 1.52561 0.41123 H 2.21364 -2.20305 0.91772 H 2.27069 0.50411 -2.39444 H 1.91120 2.88401 -3.01379 H 0.74048 4.38281 -1.43334 H -0.02826 3.56485 0.73939 H 3.35628 0.68674 1.23906 H 4.81783 -0.46166 2.87877 H 3.95870 -2.05663 2.52091 H -0.72711 1.11513 3.30621 H 0.03807 2.64939 2.83975 H -1.41838 2.07525 1.97660 Iminium 14 M06/def2-TZVP Geometry C -0.74417 1.96916 -0.42906 C 0.12979 1.96307 -1.51258 C 1.39099 2.48499 -1.34445 C 1.79572 3.01042 -0.11572 C 0.90121 2.99723 0.95067 C -0.37003 2.47717 0.80818 C 3.17341 3.55455 0.03750 S -2.34303 1.34242 -0.63611 O -3.18937 1.71656 0.43495 O -2.74894 1.36077 -1.99635 N -2.05521 -0.43873 -0.33437 C -2.30865 -1.26871 -1.29080 C -1.49635 -0.80494 0.93139 C -2.25811 -0.71057 2.08499 C -1.68846 -1.02819 3.30161 C -0.36458 -1.43684 3.34852 C 0.40022 -1.53043 2.19985 C -0.15743 -1.20589 0.97218 O 0.48300 -1.28402 -0.21278 C 1.86439 -1.41881 -0.25853 C 2.38068 -2.52842 -0.89496 C 3.75480 -2.65158 -1.02179 C 4.59222 -1.67598 -0.50986 C 4.05563 -0.56883 0.12837 C 2.68435 -0.42949 0.25318 C -2.19488 -2.68713 -1.20699 C -2.50346 -3.42710 -2.27424 H -0.18898 1.57141 -2.47110 H 2.08440 2.49420 -2.17842 H 1.20483 3.41016 1.90594 H -1.07221 2.47940 1.63317 H 3.34692 3.95391 1.03586 H 3.91421 2.77326 -0.15520 H 3.36148 4.34949 -0.68747 H -2.65943 -0.82090 -2.22056 H -3.28819 -0.38419 2.01386 H -2.27643 -0.96357 4.20750 H 0.08454 -1.69646 4.29956 H 1.43081 -1.85833 2.24795 H 1.70618 -3.27991 -1.28818 H 4.17076 -3.51799 -1.52108 H 5.66588 -1.77774 -0.60649 H 4.71102 0.19271 0.53450 H 2.24663 0.43199 0.74724 H -1.87624 -3.13341 -0.27173 H -2.44853 -4.50835 -2.25263 H -2.82379 -2.97177 -3.20565 Iminium 15 M06/def2-TZVP Geometry C 1.58831 -0.69136 -0.57439 C 1.99575 0.53890 -1.07822 C 3.19043 1.06772 -0.63842 C 3.98420 0.38830 0.28517 C 3.54612 -0.84426 0.77146 C 2.35467 -1.39231 0.35097 C 5.29485 0.94760 0.71646 S 0.11174 -1.38402 -1.14540 O -0.29158 -0.78263 -2.36127 O 0.06561 -2.78315 -0.90628 N -1.12480 -0.74666 0.05885 C -1.73040 -1.60690 0.80670 C -1.41836 0.66860 0.06856 C -0.74579 1.48595 0.97931 C -1.03141 2.84490 0.93632 C -1.95075 3.35313 0.04084 C -2.63347 2.50737 -0.81380 C -2.39197 1.14180 -0.81799 C -2.75825 -1.29695 1.74672 C -3.31396 -2.28496 2.45279 C 0.23348 0.97399 1.98695 C -3.18200 0.23811 -1.70778 H 1.38776 1.05865 -1.80875 H 3.52621 2.02327 -1.02535 H 4.16139 -1.38246 1.48378 H 2.02736 -2.35961 0.71303 H 5.54406 0.64887 1.73493 H 6.09265 0.57536 0.06725 H 5.30927 2.03571 0.65432 H -1.41998 -2.64515 0.68625 H -0.52768 3.50472 1.63397 H -2.15716 4.41641 0.02495 H -3.38266 2.90529 -1.48855 H -3.06922 -0.26390 1.85929 H -4.10126 -2.09704 3.17225 H -2.99860 -3.31612 2.33019 H 0.05479 -0.06232 2.27758 H 1.25783 1.03232 1.60964 H 0.19017 1.58133 2.89113 H -4.01144 0.78279 -2.15592 H -2.57281 -0.17055 -2.51485 H -3.60579 -0.60824 -1.16019 Iminium 16 M06/def2-TZVP Geometry N -0.66908 -0.84648 -0.04241 C -1.42364 -1.90268 -0.05049 C -1.20560 0.49514 -0.02714 C -1.78169 0.96795 1.13794 C -2.29698 2.25245 1.15253 C -2.22932 3.03944 0.01527 C -1.64678 2.54914 -1.14309 C -1.12548 1.26868 -1.17053 C 0.81261 -1.08873 -0.01215 O 1.40060 0.05054 0.04940 O 1.21308 -2.20524 -0.04381 C 2.90565 0.16400 0.06921 C 3.10487 1.65739 0.11983 C 3.44762 -0.43103 -1.20618 C 3.42048 -0.51532 1.31301 C -2.84210 -1.91248 -0.11607 C -3.47860 -3.08901 -0.09530 H -0.87880 -2.84600 -0.01657 H -1.81791 0.34013 2.02164 H -2.74927 2.63850 2.05741 H -2.63293 4.04425 0.03096 H -1.59813 3.16646 -2.03133 H -0.65999 0.87268 -2.06593 H 2.65484 2.08213 1.01840 H 4.17346 1.87669 0.13428 H 2.66726 2.13992 -0.75599 H 3.30438 -1.50972 -1.25307 H 2.98824 0.03660 -2.07956 H 4.52008 -0.23231 -1.24932 H 3.27129 -1.59401 1.28588 H 4.49286 -0.32601 1.38921 H 2.94586 -0.10363 2.20574 H -3.37892 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1.48256 -3.06072 0.68682 H -5.85534 -2.37000 -0.27704 H -5.49165 -0.69600 -0.75006 H -4.67160 -2.05892 -1.56562 H -1.52764 3.02178 0.37047 H -1.19976 5.46992 0.19501 H 0.59233 5.20267 -0.16273 Iminium 18 M06/def2-TZVP Geometry C 1.75385 -0.27451 0.53112 C 1.30466 -1.53289 0.99350 C 1.77693 -2.65108 0.32521 C 2.63692 -2.57611 -0.75830 C 3.03020 -1.31954 -1.19852 C 2.61629 -0.15281 -0.58486 S 1.19747 1.18160 1.30310 O 0.45748 0.94013 2.48526 O 2.12245 2.25533 1.21389 N -0.12586 1.69803 0.12751 C -0.07147 2.87845 -0.38798 C -1.18735 0.76045 -0.09726 C -2.26063 0.72155 0.77318 C -3.26307 -0.21262 0.58488 C -3.17968 -1.11572 -0.47449 C -2.08508 -1.06512 -1.34394 C -1.09273 -0.13418 -1.15762 C 3.14551 -3.80797 -1.42061 C 0.35883 -1.77327 2.12759 C 3.10506 1.13604 -1.16895 C -1.04730 3.44258 -1.26404 C -0.87348 4.68559 -1.71848 O -4.08617 -2.05463 -0.73927 C -5.22067 -2.16922 0.09504 H 1.45192 -3.62726 0.66966 H 3.69251 -1.24546 -2.05504 H 0.79898 3.47499 -0.11143 H -2.30536 1.41394 1.60611 H -4.10138 -0.23229 1.26765 H -2.04514 -1.77290 -2.16246 H -0.23793 -0.09631 -1.82566 H 4.10654 -4.09690 -0.98550 H 2.46403 -4.64821 -1.28806 H 3.31093 -3.65155 -2.48705 H 0.19617 -2.84411 2.23677 H 0.73675 -1.38712 3.07320 H -0.61022 -1.29893 1.95810 H 2.28797 1.80462 -1.45238 H 3.73792 1.68760 -0.47496 H 3.68147 0.93018 -2.06924 H -1.91149 2.84671 -1.53530 H -1.58960 5.15481 -2.38152 H -0.00697 5.27554 -1.43774 H -5.82020 -1.25435 0.07811 H -5.81196 -2.99000 -0.30260 H -4.93423 -2.39937 1.12549 Iminium 19 M06/def2-TZVP Geometry C 1.20988 -0.64187 0.56235 C 1.89539 0.53474 0.94386 C 3.06163 0.82970 0.25615 C 3.55416 0.03945 -0.76971 C 2.83539 -1.09257 -1.13035 C 1.66862 -1.46726 -0.49277 S -0.27017 -1.07892 1.36171 O -0.50696 -2.47824 1.38534 O -0.57192 -0.25662 2.47290 N -1.51078 -0.49796 0.12092 C -2.38245 -1.33485 -0.32820 C -1.48882 0.90071 -0.20330 C -0.71212 1.33365 -1.26545 C -0.66395 2.68809 -1.54396 C -1.38104 3.58325 -0.76610 C -2.15435 3.13263 0.29190 C -2.21069 1.78165 0.58487 C 4.83217 0.37866 -1.45234 C 1.47951 1.49429 2.01362 C 0.98582 -2.70415 -0.98740 C -3.44228 -1.02110 -1.23144 C -4.28549 -1.98618 -1.60551 H 3.60911 1.72271 0.53897 H 3.20336 -1.71361 -1.94070 H -2.28041 -2.35951 0.03212 H -0.15161 0.61698 -1.85711 H -0.06520 3.04423 -2.37292 H -1.33878 4.64244 -0.98816 H -2.71470 3.83528 0.89583 H -2.79225 1.40824 1.41980 H 5.66308 -0.14493 -0.97081 H 4.82303 0.07108 -2.49846 H 5.04739 1.44581 -1.39896 H 2.20092 2.30779 2.06532 H 0.49591 1.92580 1.81824 H 1.42526 1.02343 2.99440 H 0.95681 -3.48723 -0.23082 H -0.04756 -2.51875 -1.29179 H 1.51561 -3.08713 -1.85784 H -3.54085 -0.00249 -1.58973 H -5.10561 -1.79350 -2.28593 H -4.18250 -3.00223 -1.23841 Iminium 20 M06/def2-TZVP Geometry C 0.82883 -1.12484 0.48194 C 1.28569 -1.74159 -0.68685 C 2.50780 -1.39129 -1.19056 C 3.29254 -0.42741 -0.53859 C 2.82525 0.18423 0.62867 C 1.59233 -0.16269 1.13399 S -0.72832 -1.51531 1.08538 O -1.17095 -2.79616 0.66268 O -0.93198 -1.00816 2.39122 N -1.77046 -0.39698 0.05082 C -2.70080 -0.91722 -0.67594 C -1.45393 1.00282 0.08535 C -0.76566 1.55019 -0.98701 C -0.41566 2.88678 -0.94354 C -0.74701 3.65360 0.16262 C -1.43237 3.09065 1.22684 C -1.79031 1.75383 1.19853 O 4.46132 -0.16754 -1.10217 C -3.61980 -0.19291 -1.49269 C -4.53397 -0.86540 -2.19604 C 5.33799 0.76749 -0.49853 H 0.68593 -2.50213 -1.17298 H 2.90560 -1.85625 -2.08382 H 3.42315 0.92145 1.14629 H 1.21992 0.30139 2.03947 H -2.77722 -2.00415 -0.63235 H -0.50183 0.92603 -1.83481 H 0.11859 3.32961 -1.77486 H -0.47071 4.70037 0.19407 H -1.69398 3.69486 2.08648 H -2.31789 1.29505 2.02556 H -3.56368 0.88954 -1.51362 H -5.25937 -0.35732 -2.81915 H -4.58556 -1.94903 -2.16897 H 4.88595 1.76209 -0.45792 H 5.62045 0.44833 0.50800 H 6.22435 0.80148 -1.12614 Iminium 21 M06/def2-TZVP Geometry C 1.87780 -0.40226 0.54237 C 2.73936 -0.46840 -0.54758 C 2.96811 -1.69289 -1.13468 C 2.35330 -2.84936 -0.65292 C 1.49362 -2.74849 0.43921 C 1.24606 -1.53424 1.04311 C 2.64040 -4.17156 -1.27451 S 1.53161 1.13889 1.24432 O 0.86628 1.01055 2.48702 O 2.56245 2.08463 1.00226 N 0.20234 1.69943 0.11005 C 0.39685 2.77888 -0.57215 C -0.94653 0.85250 -0.01386 C -1.09144 0.08625 -1.16753 C -2.15641 -0.77129 -1.28083 C -3.08825 -0.87956 -0.24267 C -2.92964 -0.11120 0.91034 C -1.85409 0.75022 1.02426 O -4.08411 -1.73814 -0.44743 C -5.07007 -1.90171 0.55214 C -0.54439 3.37653 -1.46162 C -0.20727 4.49335 -2.11139 H 3.23174 0.42567 -0.91207 H 3.64411 -1.76437 -1.97947 H 1.01405 -3.64267 0.82121 H 0.57951 -1.45555 1.89338 H 1.81376 -4.86892 -1.13876 H 2.85070 -4.07763 -2.34021 H 3.52324 -4.62086 -0.81062 H 1.36278 3.26206 -0.42305 H -0.35399 0.16053 -1.96077 H -2.29684 -1.38077 -2.16477 H -3.64092 -0.17524 1.72227 H -1.72161 1.34175 1.92177 H -5.77331 -2.63744 0.17072 H -4.63298 -2.27190 1.48405 H -5.60006 -0.96426 0.74364 H -1.51945 2.91737 -1.57828 H -0.89563 4.99036 -2.78349 H 0.77120 4.94663 -1.98988 Iminium 22 M06/def2-TZVP Geometry C -1.28491 -0.88074 0.45130 C -1.78626 -1.51693 -0.68107 C -2.94139 -1.04050 -1.25801 C -3.56477 0.05962 -0.68851 C -3.07524 0.69488 0.44102 C -1.91770 0.22141 1.01843 F -4.66492 0.51318 -1.24013 S 0.19477 -1.44957 1.13960 O 0.41230 -0.90556 2.42698 O 0.45604 -2.80215 0.80015 N 1.39937 -0.54395 0.09410 C 2.25537 -1.22615 -0.59207 C 1.29900 0.88961 0.07351 C 0.71793 1.49327 -1.03175 C 0.57677 2.86836 -1.04332 C 1.00762 3.61741 0.04065 C 1.58506 2.99821 1.13731 C 1.73351 1.62233 1.16474 C 3.28736 -0.67804 -1.40856 C 4.10045 -1.50696 -2.06920 H -1.28387 -2.38627 -1.08827 H -3.37911 -1.50806 -2.13055 H -3.61042 1.54184 0.85052 H -1.50680 0.68990 1.90451 H 2.16624 -2.30986 -0.51066 H 0.37378 0.88472 -1.86209 H 0.12710 3.35550 -1.89946 H 0.89396 4.69440 0.02927 H 1.92531 3.58825 1.97904 H 2.17448 1.12145 2.01765 H 3.39695 0.39891 -1.46639 H 4.90524 -1.13728 -2.69248 H 3.98592 -2.58429 -2.00597 Iminium 23 M06/def2-TZVP Geometry C -0.69101 -1.77409 0.27542 C -1.56550 -1.16062 1.16423 C -2.86737 -0.94614 0.76418 C -3.30514 -1.32801 -0.50217 C -2.40045 -1.93880 -1.37217 C -1.09604 -2.16695 -0.99635 S 0.95959 -1.99010 0.73283 O 1.14921 -1.80344 2.12233 O 1.59788 -3.01374 -0.01507 N 1.68927 -0.46822 0.00346 C 2.66134 -0.59360 -0.83563 C 1.12116 0.79054 0.40402 C 1.40800 1.29972 1.65980 C 0.80347 2.49059 2.01835 C -0.06206 3.14896 1.16043 C -0.33849 2.61789 -0.09734 C 0.26436 1.41964 -0.47642 C -4.72130 -1.12314 -0.91356 O -1.15800 3.16625 -0.99884 C -1.78817 4.39174 -0.68706 C 3.37665 0.48167 -1.44149 C 4.36414 0.20349 -2.29611 H -1.22416 -0.86411 2.14869 H -3.56514 -0.47554 1.44762 H -2.73644 -2.24587 -2.35639 H -0.39914 -2.65626 -1.66661 H 2.94795 -1.61861 -1.07308 H 2.07491 0.77436 2.33047 H 1.01062 2.91997 2.99080 H -0.51802 4.07719 1.47748 H 0.03732 0.99246 -1.44741 H -4.79887 -0.88352 -1.97467 H -5.29663 -2.03875 -0.74927 H -5.19909 -0.33080 -0.33789 H -2.43854 4.29403 0.18729 H -1.05386 5.18245 -0.50745 H -2.39101 4.65561 -1.55232 H 3.10925 1.50032 -1.18485 H 4.94265 0.98592 -2.77123 H 4.62579 -0.81944 -2.54674 Iminium 24 M06/def2-TZVP Geometry C -1.49113 -0.73633 0.62698 C -2.18986 -1.43695 -0.35084 C -3.28366 -0.83893 -0.93554 C -3.69121 0.44225 -0.56076 C -2.96896 1.11730 0.42136 C -1.86871 0.54214 1.02032 S -0.07919 -1.44830 1.32117 O 0.35257 -0.74495 2.47062 O -0.08535 -2.86441 1.22544 N 1.16522 -0.97882 0.05233 C 1.84176 -1.91710 -0.52012 C 1.28812 0.41835 -0.26055 C 0.72366 0.87928 -1.43792 C 0.79675 2.23355 -1.71170 C 1.41625 3.08980 -0.81983 C 1.98674 2.62473 0.36288 C 1.91087 1.26589 0.63982 C -4.89860 1.05952 -1.17556 C 2.67654 3.56284 1.29608 C 2.87938 -1.72357 -1.47966 C 3.49673 -2.79098 -1.99214 H -1.88543 -2.43872 -0.63059 H -3.84577 -1.37363 -1.69313 H -3.28140 2.11130 0.72109 H -1.30864 1.06538 1.78579 H 1.58790 -2.93280 -0.21508 H 0.22432 0.18982 -2.11049 H 0.36248 2.62156 -2.62474 H 1.46355 4.15079 -1.04184 H 2.33032 0.86752 1.55681 H -5.03213 0.73850 -2.20898 H -4.85370 2.14817 -1.14761 H -5.79528 0.75747 -0.62674 H 2.08871 4.46947 1.44846 H 3.64131 3.87409 0.88778 H 2.85979 3.10514 2.26783 H 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1.96400 H 1.34400 3.03635 -1.50312 H 0.59981 5.09194 -2.66921 H -1.07122 4.91892 -1.90258 H 5.63113 -0.66083 0.78241 H 4.72984 -2.04728 1.46041 H 5.91242 -2.30069 0.15794 Iminium 27 M06/def2-TZVP Geometry C -1.39987 -1.03115 0.41766 C -1.94910 0.08822 1.03612 C -3.05920 0.68136 0.47707 C -3.58680 0.14416 -0.68585 C -3.04776 -0.97324 -1.30600 C -1.93978 -1.56912 -0.74739 S 0.02226 -1.74582 1.09115 O 0.27219 -1.26747 2.39909 O 0.17678 -3.10218 0.70512 N 1.30955 -0.90327 0.08897 C 2.14772 -1.63238 -0.57143 C 1.29099 0.53153 0.07590 C 1.69659 1.23836 1.19700 C 1.61921 2.61739 1.18463 C 1.13251 3.25282 0.05635 C 0.72362 2.55317 -1.06578 C 0.80137 1.17587 -1.05190 F -4.64167 0.71097 -1.21994 F 1.05537 4.56594 0.04822 C 3.24520 -1.14509 -1.33882 C 4.03402 -2.01921 -1.97035 H -1.51287 0.47589 1.94857 H -3.52986 1.54640 0.92618 H -3.51353 -1.36098 -2.20282 H -1.50497 -2.45531 -1.19438 H 1.98630 -2.70885 -0.50586 H 2.06452 0.71307 2.06960 H 1.93321 3.20843 2.03545 H 0.34976 3.09331 -1.92610 H 0.47360 0.59435 -1.90752 H 3.42576 -0.07700 -1.38068 H 4.88875 -1.69689 -2.55208 H 3.84906 -3.08754 -1.92306 Iminium 28 M06/def2-TZVP Geometry C -2.07236 -1.39474 0.20018 C -1.08688 -2.23873 0.69771 C -0.76464 -3.36895 -0.02882 C -1.41531 -3.63415 -1.22406 C -2.40004 -2.78214 -1.70517 C -2.73849 -1.64903 -0.99367 S -2.45250 0.05536 1.06985 O -3.74897 0.54253 0.76444 O -1.90329 0.04404 2.37307 N -1.37110 1.24316 0.17229 C -1.91839 2.26419 -0.39988 C 0.03327 0.94650 0.13512 C 0.56522 0.42099 -1.03445 C 1.90158 0.08363 -1.06476 C 2.68673 0.26698 0.06584 C 2.14455 0.79274 1.22452 C 0.80336 1.13567 1.26741 C 4.13963 -0.12959 -0.01081 C -1.22347 3.30233 -1.08554 C -1.92418 4.29960 -1.63314 F 4.75099 0.52912 -0.98996 F 4.78329 0.11738 1.11797 F 4.25012 -1.42925 -0.27423 H -0.59620 -2.01292 1.63668 H -0.00692 -4.04766 0.34164 H -1.15801 -4.52380 -1.78632 H -2.91210 -3.01011 -2.63143 H -3.51805 -0.98105 -1.34051 H -3.00507 2.31657 -0.32373 H -0.07098 0.26988 -1.90027 H 2.34090 -0.32803 -1.96605 H 2.76686 0.93698 2.09812 H 0.36029 1.53857 2.16947 H -0.14117 3.26788 -1.13846 H -1.43946 5.11575 -2.15455 H -3.00747 4.33043 -1.57530 Iminium 29 M06/def2-TZVP Geometry C -4.49442 0.63692 0.12130 C -3.25592 1.23588 0.09552 C -2.08516 0.47926 -0.05610 C -2.23342 -0.90805 -0.21235 C -3.47361 -1.49734 -0.20434 C -4.63188 -0.74048 -0.02588 C -5.96856 -1.39156 0.01925 C -0.78380 1.11855 -0.06402 C -0.74689 2.59001 -0.29337 C 0.35369 0.37833 0.16132 C 1.64783 0.90208 0.14863 H 1.78874 1.95422 -0.07830 N 2.76482 0.26656 0.39283 C 4.06314 0.94383 0.34393 C 4.98698 0.19727 -0.59775 O 5.10784 -1.14111 -0.20772 C 3.87425 -1.79752 -0.24607 C 2.88710 -1.15603 0.71246 H -5.38103 1.24703 0.25375 H -3.20028 2.30989 0.21869 H -1.36783 -1.53398 -0.39085 H -3.55947 -2.56859 -0.35061 H -6.02005 -2.24635 -0.65632 H -6.17228 -1.76750 1.02641 H -6.76655 -0.69406 -0.23484 H -1.17928 3.11081 0.56520 H 0.25082 2.99190 -0.44184 H -1.34989 2.85811 -1.16183 H 0.23509 -0.67039 0.39654 H 3.91725 1.97685 0.02689 H 4.48539 0.93924 1.35397 H 5.98217 0.64264 -0.57189 H 4.60482 0.26757 -1.62820 H 4.04206 -2.83640 0.04055 H 3.45971 -1.78475 -1.26632 H 3.26072 -1.23558 1.73821 H 1.91760 -1.64471 0.65767 Iminium 30 M06/def2-TZVP Geometry C 3.38613 -1.16910 -0.59572 C 2.12317 -0.62873 -0.65116 C 1.84026 0.61236 -0.06756 C 2.88393 1.29815 0.56398 C 4.14645 0.75483 0.64179 C 4.40628 -0.48372 0.06162 C 0.50050 1.19019 -0.12634 C 0.39596 2.66923 -0.00612 C -0.58546 0.36743 -0.25675 C -1.90728 0.82381 -0.37462 H -2.09074 1.89285 -0.42692 N -2.98797 0.09943 -0.44691 C -4.31562 0.70732 -0.59108 C -5.22160 0.20785 0.51777 O -5.28048 -1.18925 0.50961 C -4.02297 -1.75473 0.73419 C -3.04752 -1.36227 -0.36236 H 3.59931 -2.12049 -1.06644 H 1.35632 -1.16115 -1.20012 H 2.70655 2.26009 1.02730 H 4.94219 1.28500 1.14954 H 1.12317 3.15917 -0.65513 H -0.58833 3.06582 -0.23842 H 0.63082 2.97497 1.01756 H -0.41477 -0.70082 -0.25207 H -4.21641 1.79292 -0.57257 H -4.71862 0.40331 -1.56203 H -6.23310 0.58610 0.36580 H -4.85875 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0.90829 H 4.28965 -1.27344 1.81941 H 2.79957 -1.76414 -0.07930 H 4.16183 -1.67613 -1.21203 C -3.65837 0.42615 0.18860 C -3.78263 -0.94240 -0.17008 C -5.04645 -1.55053 -0.10849 C -6.13993 -0.83449 0.29500 C -6.02029 0.52016 0.65295 C -4.80593 1.13823 0.60155 H -5.14116 -2.59479 -0.38489 H -7.11102 -1.31268 0.34056 H -6.89842 1.06929 0.96933 H -4.70387 2.18298 0.87492 Iminium 35 M06/def2-TZVP Geometry C 2.93991 1.05268 -0.11750 C 2.63517 -0.31094 0.01098 C 3.68228 -1.22233 0.20508 C 4.98896 -0.78982 0.26923 C 1.30168 -0.81697 -0.04758 C 0.14632 -0.12021 -0.22686 C -1.06787 -0.82026 -0.26153 H -1.02020 -1.90212 -0.14838 N -2.26962 -0.34317 -0.42284 C -3.45186 -1.21051 -0.43858 C -4.44798 -0.71954 0.59356 O -4.77326 0.62110 0.36124 C -3.65008 1.44592 0.46699 C -2.60560 1.07443 -0.57082 H 2.14905 1.77788 -0.26902 H 3.45211 -2.27780 0.30475 H 5.79112 -1.50110 0.41933 H 0.16301 0.95549 -0.34839 H -3.89662 -1.15376 -1.43696 H -3.14439 -2.23855 -0.24538 H -4.03142 -0.84839 1.60471 H -5.36735 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4.40627 -0.22220 H -2.25433 5.18748 1.76528 H -2.56795 2.96774 2.80271 H -2.59288 0.93760 1.39210 H -1.99169 3.35183 -2.08843 H -1.97058 5.37993 -0.67967 C -3.26753 -3.67063 1.43809 C -2.13408 -2.94467 1.76911 C -1.47185 -2.21540 0.79896 C -1.93879 -2.20438 -0.51036 C -3.07827 -2.92632 -0.83303 C -3.73839 -3.66163 0.13736 H -3.78472 -4.24335 2.19813 H -1.76323 -2.95150 2.78690 H -0.58369 -1.64943 1.06629 H -3.44955 -2.91745 -1.85312 H -4.62551 -4.22519 -0.12444 Iminium 39 M06/def2-TZVP Geometry C 5.22295 0.20595 0.39491 C 4.16250 -0.56047 -0.10272 C 4.37099 -1.92543 -0.34311 C 5.59699 -2.49585 -0.09175 C 2.90931 0.09045 -0.34345 C 1.76181 -0.45517 -0.81852 C 0.63333 0.37268 -0.98162 H 0.73372 1.41785 -0.69179 N -0.53866 0.04407 -1.43122 C -1.64691 1.02835 -1.53521 C -0.90685 -1.31023 -1.86133 H 5.06745 1.26320 0.58226 H 3.56702 -2.54103 -0.72938 H 5.75206 -3.55093 -0.27962 H 1.70795 -1.50989 -1.05957 H -2.55044 0.47412 -1.26441 H -1.42980 -1.21067 -2.81649 C 6.45132 -0.36809 0.64556 C 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1.39004 3.18448 -0.86476 F -2.17997 3.27200 -0.17356 F -1.32509 2.47020 1.62035 F -0.33004 4.06497 0.57875 F 3.10505 2.76783 -2.59618 F 3.88846 1.14736 -1.42830 F 3.14021 0.77967 -3.40624 F 5.54638 -1.14261 -0.08608 F 4.31793 -1.92933 -1.66572 H 2.26643 -3.31540 -0.44708 C 1.99752 0.89394 2.84800 F 3.04774 0.93644 3.65455 F 2.00210 2.02016 2.12924 F 0.90197 0.89899 3.59589 Iminium 46 M06/def2-TZVP Geometry C -5.29833 -0.20845 -1.32459 C -5.17031 -1.00728 -0.15275 C -6.29096 -1.22085 0.63986 C -3.94868 -1.60140 0.25197 C -2.73308 -1.52991 -0.37222 C -1.64216 -2.19539 0.18990 H -1.81525 -2.73653 1.11858 N -0.41376 -2.25986 -0.25978 C 0.60968 -3.03920 0.46032 C 0.01954 -1.61150 -1.50429 H -4.43576 -0.02811 -1.95435 H -6.20196 -1.82812 1.53630 H -2.61717 -0.96113 -1.28705 H 0.87637 -3.89656 -0.16532 H 0.74996 -2.27560 -1.97301 C -6.49531 0.33191 -1.65707 H -6.59285 0.94144 -2.54865 H -3.99577 -2.18258 1.17226 H -0.83741 -1.56689 -2.17931 H 0.14371 -3.42329 1.37035 C 1.75357 -1.17542 1.68043 C 1.82952 -2.22700 0.77249 C 2.43312 1.29336 -1.65973 C 1.85650 0.05202 -1.86120 C 0.62820 -0.25063 -1.29191 C -0.01054 0.70810 -0.52365 C 4.05518 -0.63280 1.25461 C 2.85738 -0.38488 1.91580 C 1.79928 2.24517 -0.87864 C 0.57643 1.94392 -0.31145 H -0.96659 0.49873 -0.05341 C -0.15297 2.92821 0.56141 C 3.80309 1.57716 -2.21699 H 2.37844 -0.68982 -2.45746 H 0.82081 -0.96409 2.19486 H 4.91659 0.00002 1.43405 C 3.02345 -2.48142 0.12816 C 4.13385 -1.68139 0.36481 C 5.39492 -1.97767 -0.40107 F 6.38127 -1.15994 -0.08313 H 2.26177 3.20858 -0.70536 F 4.02253 0.90772 -3.34071 F 3.97539 2.86655 -2.46263 F 4.74249 1.20636 -1.34057 F 0.54473 4.02855 0.77383 F -1.31762 3.27542 0.01133 F -0.43368 2.38133 1.74696 F 5.17152 -1.86717 -1.71389 F 5.79959 -3.22537 -0.17908 H 3.09898 -3.30234 -0.57984 C 2.79544 0.78245 2.86406 F 3.77810 0.73090 3.75264 F 2.92430 1.93205 2.19629 F 1.64518 0.82727 3.52291 C -7.53565 -0.67546 0.31687 C -7.64735 0.12036 -0.85750 C -8.89481 0.66973 -1.18485 C -9.98407 0.44215 -0.38620 C -9.87676 -0.34338 0.77419 C -8.67695 -0.89173 1.12004 H -8.98413 1.27698 -2.07865 H -10.94297 0.87221 -0.64964 H -10.75118 -0.50985 1.39074 H -8.58075 -1.49958 2.01309 Iminium 47 M06/def2-TZVP Geometry C -5.19243 0.70788 -1.61797 C -5.28225 -0.36741 -0.73555 C -4.13305 -1.14498 -0.44036 C -2.87719 -1.04587 -0.97868 C -1.87705 -1.90469 -0.52161 H -2.14863 -2.61686 0.25562 N -0.62671 -1.97054 -0.91000 C 0.29242 -2.95963 -0.32020 C -0.06485 -1.10689 -1.95621 H -4.24126 0.94073 -2.08114 H -2.65262 -0.31184 -1.74296 H 0.56260 -3.67379 -1.10416 H 0.65846 -1.70843 -2.51220 C -6.28232 1.50908 -1.91219 H -6.17622 2.34056 -2.59672 H -4.25354 -1.91801 0.31383 H -0.86492 -0.85850 -2.65654 H -0.26375 -3.50276 0.44699 C 2.75316 -2.51448 -0.35175 C 1.52461 -2.32302 0.24793 C 0.59611 2.08243 -0.01577 C -0.04041 0.96049 -0.51803 C 0.60444 0.13080 -1.41999 C 1.89212 0.45005 -1.82517 C 3.78491 -1.03727 1.23126 C 3.88134 -1.86788 0.13633 C 1.87966 2.39838 -0.41720 C 2.52170 1.57799 -1.32972 H 2.41660 -0.18992 -2.52747 C 3.94592 1.86910 -1.72395 C -0.15670 2.93709 0.96679 H -1.04409 0.73356 -0.17204 H 2.84380 -3.16422 -1.21806 H 4.66244 -0.52822 1.61192 C 1.42977 -1.49357 1.36081 C 2.55098 -0.85552 1.84530 C 2.46662 0.07662 3.02428 F 1.29774 -0.01390 3.64543 H 2.37961 3.27164 -0.01778 F -0.61425 2.19713 1.97931 F 0.58772 3.90413 1.46949 F -1.22143 3.49384 0.38538 F 4.20862 3.16628 -1.68943 F 4.79031 1.26571 -0.88183 F 4.21606 1.42349 -2.94385 F 2.61627 1.34356 2.62763 F 3.42251 -0.17558 3.90695 H 0.47013 -1.33515 1.84399 C 5.18650 -2.08441 -0.58107 F 6.18279 -1.42010 -0.02525 F 5.50558 -3.37584 -0.59943 F 5.08316 -1.68956 -1.85317 C -7.49384 1.24209 -1.32250 H -8.35502 1.86442 -1.54287 C -6.54830 -0.66174 -0.11478 C -7.65804 0.17231 -0.42738 C -8.91610 -0.07846 0.15886 C -9.08734 -1.11711 1.02443 C -7.99878 -1.94502 1.33110 C -6.76619 -1.72558 0.77709 H -9.74364 0.57398 -0.09665 H -10.05444 -1.30682 1.47256 H -8.13434 -2.77324 2.01623 H -5.96236 -2.40057 1.04175 Iminium 48 M06/def2-TZVP Geometry C 4.85101 -0.73176 -0.72664 C 4.56172 -1.51163 0.40812 C 3.27184 -2.01608 0.69874 C 2.11663 -1.85120 -0.01880 C 0.93979 -2.43604 0.44748 H 0.99908 -2.99860 1.37759 N -0.25343 -2.39943 -0.09481 C -1.38331 -3.11034 0.53028 C -0.53786 -1.70568 -1.35684 H 4.06510 -0.47761 -1.42835 H 2.11370 -1.26737 -0.93170 H -1.02595 -3.51619 1.47915 H 0.36717 -1.72782 -1.96747 C 6.11876 -0.27236 -0.95396 H 6.31123 0.34975 -1.81922 H 3.19969 -2.60682 1.61166 H -1.28519 -2.29993 -1.88843 H -1.64501 -3.95425 -0.11568 C -3.71508 -2.40872 -0.02917 C -2.57642 -2.22612 0.73057 C -0.89492 1.85687 -0.11297 C -0.40054 0.57879 -0.30989 C -1.04252 -0.29965 -1.16579 C -2.17821 0.12656 -1.84068 C -4.74448 -0.50651 1.00835 C -4.79530 -1.54768 0.10627 C -2.02591 2.27979 -0.78112 C -2.66076 1.40890 -1.65136 H -2.70281 -0.54977 -2.50811 C -3.93915 1.84447 -2.31692 C -0.17460 2.74596 0.86215 H 0.48217 0.27255 0.24310 H -3.76888 -3.22300 -0.74668 H -5.58485 0.16895 1.11231 C -2.53089 -1.18506 1.65160 C -3.60662 -0.33251 1.78704 C -3.54432 0.83239 2.73896 F -2.62796 0.65038 3.68115 H -2.42086 3.27479 -0.61814 F -0.78053 3.90603 1.03306 F -0.07795 2.14950 2.05321 F 1.07173 2.98689 0.45036 F -4.97262 1.66457 -1.48791 F -3.90803 3.12970 -2.63716 F -4.18458 1.14965 -3.41878 F -4.71007 1.03993 3.33144 F -3.22609 1.95296 2.08138 H -1.64285 -1.03117 2.25810 C -5.98805 -1.76528 -0.78530 F -6.45148 -3.00594 -0.66302 F -6.97379 -0.92732 -0.52184 F -5.63776 -1.60268 -2.06498 C 7.17040 -0.55703 -0.06542 C 5.61379 -1.79734 1.29529 C 6.88187 -1.33146 1.06560 H 5.41249 -2.40571 2.17089 H 7.67793 -1.59077 1.75223 C 11.10016 0.89197 -0.79044 C 10.26242 0.59665 -1.85367 C 8.98337 0.13433 -1.61939 C 8.52130 -0.05805 -0.31537 C 9.38106 0.23697 0.74511 C 10.65412 0.71454 0.50929 H 12.10174 1.26104 -0.97493 H 10.61079 0.72346 -2.87135 H 8.34765 -0.11656 -2.46077 H 9.03626 0.12709 1.76685 H 11.30176 0.95486 1.34348 Iminium 49 M06/def2-TZVP Geometry C -5.89318 -0.39668 -1.07598 C -5.71338 -1.14215 0.10341 C -4.46770 -1.70452 0.48571 C -3.27403 -1.64147 -0.17739 C -2.15459 -2.26286 0.38189 H -2.29262 -2.76992 1.33538 N -0.93765 -2.31725 -0.09612 C 0.12184 -3.04558 0.62711 C -0.55051 -1.70745 -1.37546 H -5.05968 -0.22706 -1.74757 H -3.19229 -1.10895 -1.11753 H 0.38057 -3.92912 0.03552 H 0.19096 -2.36742 -1.83225 C -7.12019 0.12448 -1.38611 H -7.24994 0.69947 -2.29666 H -4.47574 -2.24998 1.42911 H -1.42205 -1.71789 -2.03311 H -0.30805 -3.39019 1.57011 C 2.51519 -2.47617 0.18905 C 1.33883 -2.20242 0.85715 C 1.75275 1.26970 -1.71446 C 1.21459 0.00375 -1.85522 C 0.01804 -0.32057 -1.23038 C -0.62542 0.64091 -0.47041 C 3.55778 -0.55917 1.18483 C 3.62283 -1.65378 0.35087 C 1.11468 2.22503 -0.94004 C -0.07461 1.90246 -0.31852 H -1.55539 0.41589 0.04262 C -0.80312 2.88789 0.55346 C 3.08900 1.60041 -2.32502 H 1.74284 -0.74035 -2.44301 H 2.57976 -3.33231 -0.47699 H 4.41616 0.09157 1.30480 C 1.27893 -1.10810 1.71451 C 2.37863 -0.29282 1.87255 C 2.32850 0.91993 2.76319 F 3.36001 0.94783 3.59480 H 1.55266 3.20723 -0.81272 F 4.05806 1.44930 -1.41679 F 3.37324 0.80934 -3.34989 F 3.13337 2.85559 -2.74636 F -2.00277 3.17335 0.04382 F -1.01259 2.37043 1.76666 F -0.13963 4.01919 0.70050 F 1.21551 0.96058 3.48359 F 2.37772 2.03722 2.03187 H 0.36156 -0.88421 2.25086 C 4.86287 -1.97860 -0.43766 F 5.86276 -1.16120 -0.16436 F 5.26365 -3.22354 -0.19657 F 4.60612 -1.89625 -1.74655 C -8.22360 -0.06909 -0.54443 C -6.82064 -1.33368 0.94336 C -8.04987 -0.80740 0.62346 H -6.69672 -1.90601 1.85677 H -8.89524 -0.96453 1.28335 C -9.54294 0.51154 -0.90600 H -10.31152 0.26899 -0.17377 H -9.47505 1.59963 -0.98581 H -9.86995 0.14793 -1.88342 Iminium 50 M06/def2-TZVP Geometry C -6.84691 -1.42744 1.05397 C -5.77276 -1.15781 0.19641 C -4.51300 -1.75026 0.49537 C -3.34228 -1.63412 -0.19608 C -2.20805 -2.30539 0.27409 N -1.01058 -2.32864 -0.24930 C -0.66175 -1.61830 -1.48811 C 0.07089 -3.11032 0.38052 C -8.08567 -0.87634 0.80555 C -0.67491 0.66022 -0.41436 C -0.06303 -0.25742 -1.25026 C 2.27774 -0.45444 1.89281 C 1.19582 -1.27455 1.65630 C 1.27327 -2.27065 0.68819 C 2.44848 -2.44258 -0.01554 C 1.09911 2.23326 -0.78900 C -0.09273 1.89501 -0.18022 C 3.45475 -0.61687 1.17080 C 3.53669 -1.61290 0.22220 C 4.77537 -1.81461 -0.60924 C 2.20340 0.65821 2.90487 C 1.13427 0.08361 -1.86367 C 1.70692 1.32110 -1.63653 C 3.05081 1.65282 -2.22969 F 3.13842 2.93465 -2.55106 F 2.16200 1.84376 2.29008 F 1.12220 0.56370 3.66717 F 3.26680 0.66090 3.69548 F 5.21903 -3.06368 -0.49957 F 4.49934 -1.60943 -1.90058 F 5.75188 -0.99618 -0.26456 F 4.01747 1.39573 -1.34212 F 3.30328 0.93431 -3.31415 C -0.78336 2.82397 0.77981 F -0.91344 2.24145 1.97445 F -0.13050 3.95855 0.94553 F -2.01516 3.11242 0.35530 C -8.26064 -0.05520 -0.29329 C -5.97781 -0.32038 -0.91271 C -7.21046 0.23776 -1.17073 C -7.44312 1.13117 -2.34270 H -6.69403 -2.07222 1.91247 H -4.49502 -2.37078 1.39095 H -3.28729 -1.02670 -1.09156 H -2.31851 -2.88683 1.18798 H -1.55760 -1.56157 -2.10928 H 0.05052 -2.24867 -2.02598 H 0.33745 -3.91913 -0.30636 H -0.34161 -3.56297 1.28480 H -8.91770 -1.08344 1.46653 H -1.60428 0.42029 0.09345 H 0.27893 -1.13101 2.22046 H 2.52599 -3.22049 -0.77040 H 1.56129 3.19359 -0.59646 H 4.29846 0.03907 1.35063 H 1.63359 -0.62577 -2.51529 H -9.23674 0.37873 -0.48685 H -5.15600 -0.09912 -1.58577 H -8.21799 0.72421 -2.99596 H -7.78499 2.11688 -2.01972 H -6.53834 1.26566 -2.93495 Iminium 51 M06/def2-TZVP Geometry C -5.86506 0.10417 -1.46282 C -5.83537 -0.75173 -0.34654 C -4.63347 -1.40935 0.03822 C -3.40804 -1.35099 -0.56376 C -2.35021 -2.08207 -0.01368 N -1.11748 -2.16520 -0.44245 C -0.63548 -1.46777 -1.64323 C -0.13401 -3.01275 0.25864 C -7.01773 0.74390 -1.83799 C 1.25588 0.15755 -1.86887 C 0.00434 -0.13697 -1.34772 C 2.14634 -0.49823 1.89793 C 1.02849 -1.24539 1.59758 C 1.09978 -2.25425 0.64194 C 2.30310 -2.51267 0.01697 C 1.23211 2.30053 -0.77925 C 1.86133 1.36965 -1.58868 C 3.35454 -0.74992 1.25737 C 3.42861 -1.75770 0.32120 C 4.69998 -2.05022 -0.42936 C 2.08775 0.62989 2.89285 C -0.62919 0.80176 -0.55090 C -0.01510 2.00859 -0.26258 C -0.74476 2.97194 0.63313 F -0.03127 4.04799 0.90625 F 2.27568 1.80062 2.27770 F 0.91616 0.68536 3.51264 F 3.03580 0.51001 3.81132 F 5.05910 -3.32123 -0.27238 F 4.51421 -1.85514 -1.73838 F 5.70227 -1.28511 -0.03939 F -1.88897 3.36465 0.07039 F -1.06515 2.38317 1.78806 C 3.25575 1.63909 -2.09020 F 4.15549 1.19474 -1.20592 F 3.49024 1.02139 -3.23996 F 3.47342 2.93315 -2.26271 C -8.17664 0.53807 -1.09860 C -7.01920 -0.95722 0.40484 C -8.16975 -0.29959 0.00226 H -4.96195 0.26766 -2.03849 H -4.69598 -2.03785 0.92392 H -3.24900 -0.74634 -1.44834 H -2.56043 -2.66213 0.88336 H -1.47393 -1.36624 -2.33500 H 0.08791 -2.12919 -2.12609 H 0.12246 -3.84237 -0.40714 H -0.63380 -3.43098 1.13507 H -7.02560 1.40144 -2.69765 H 1.77358 -0.56794 -2.48851 H 0.08806 -1.03066 2.09640 H 2.37501 -3.30004 -0.72853 H 1.71680 3.23989 -0.54504 H 4.22754 -0.15058 1.48834 H -1.60386 0.59875 -0.11759 H -9.09477 1.03769 -1.38451 C -7.06700 -1.85020 1.60169 H -9.08321 -0.44733 0.56668 H -8.06911 -1.86307 2.02695 H -6.80655 -2.88209 1.35360 H -6.38544 -1.51723 2.38841 Iminium 52 M06/def2-TZVP Geometry C -5.35350 -2.05817 1.40295 C -4.34764 -1.68265 0.49890 C -3.03937 -2.19425 0.68962 C -1.92088 -1.95645 -0.06157 C -0.71632 -2.55752 0.30758 N 0.45142 -2.45520 -0.27635 C 0.67658 -1.65112 -1.48475 C 1.62042 -3.18440 0.24757 C -6.63639 -1.58550 1.26576 C 0.51032 0.55612 -0.28399 C 1.16456 -0.25628 -1.19501 C 3.73996 -0.46057 1.76536 C 2.70012 -1.33872 1.54965 C 2.77986 -2.27664 0.52515 C 3.91568 -2.33038 -0.25762 C 2.10859 2.31005 -0.64965 C 0.98413 1.82736 -0.00885 C 4.87615 -0.50492 0.96560 C 4.96039 -1.44105 -0.04162 C 6.15430 -1.51762 -0.95491 C 3.66421 0.58584 2.84497 C 2.29257 0.22938 -1.83997 C 2.75688 1.50470 -1.57099 C 4.02394 1.98857 -2.22570 F 4.03837 3.30637 -2.35165 F 4.77366 0.60998 3.56973 F 3.51424 1.79928 2.30717 F 2.64116 0.38032 3.66415 F 5.77997 -1.30414 -2.21982 F 7.08166 -0.62996 -0.64733 F 6.70445 -2.72805 -0.91119 F 5.08491 1.64410 -1.48882 F 4.18656 1.45519 -3.42924 C 0.23574 2.65251 1.00166 F -0.99805 2.92052 0.56931 F 0.10485 1.98253 2.14886 F 0.83590 3.79885 1.26268 C -6.97394 -0.71996 0.22608 C -4.68982 -0.81059 -0.55072 C -5.97067 -0.34446 -0.67912 H -5.10566 -2.72947 2.21864 H -2.92078 -2.85543 1.54781 H -1.96508 -1.30201 -0.92401 H -0.72932 -3.19500 1.19005 H -0.25028 -1.63983 -2.06174 H 1.41324 -2.18454 -2.09041 H 1.90018 -3.94073 -0.49218 H 1.29879 -3.70614 1.15154 H -7.40199 -1.88389 1.97309 H -0.36897 0.20323 0.24622 H 1.81349 -1.28679 2.17479 H 3.99504 -3.06194 -1.05729 H 2.48278 3.30169 -0.42887 H 5.68640 0.19481 1.13312 H 2.82358 -0.39332 -2.55292 H -6.21362 0.32747 -1.49412 H -3.93858 -0.49869 -1.26711 C -10.45653 -0.24434 -1.32597 C -9.02156 -0.72731 -1.21277 C -8.37225 -0.21536 0.07704 C -8.44962 1.31211 0.14045 C -9.88748 1.78605 0.02451 C -10.53671 1.26985 -1.24728 H -11.04865 -0.68259 -0.51268 H -10.89707 -0.60664 -2.25795 H -8.44601 -0.36334 -2.07400 H -8.97350 -1.82012 -1.24370 H -8.95886 -0.61015 0.91807 H -7.99418 1.66921 1.06900 H -7.86139 1.73917 -0.68210 H -10.45514 1.42960 0.89332 H -9.92229 2.87752 0.06023 H -10.02484 1.70424 -2.11592 H -11.57651 1.59954 -1.30514 Iminium 53 M06/def2-TZVP Geometry C 5.90277 -0.35042 -1.09718 C 5.73025 -1.10095 0.07941 C 4.48419 -1.66947 0.45965 C 3.29138 -1.60709 -0.20122 C 2.17478 -2.24298 0.35304 N 0.96088 -2.30450 -0.12715 C 0.56739 -1.68431 -1.40037 C -0.09411 -3.04897 0.58822 C 7.12492 0.17837 -1.41894 C -1.22881 0.00090 -1.84783 C -0.02066 -0.30745 -1.24016 C -3.58879 -1.63553 0.34617 C -2.48513 -2.45785 0.16193 C -1.30927 -2.21052 0.84195 C -1.24643 -1.14459 1.73357 C -1.14701 2.22461 -0.93820 C -1.78329 1.26007 -1.70139 C -3.52302 -0.57294 1.22084 C -2.34501 -0.33326 1.91899 C -2.29083 0.84841 2.85030 C -4.82989 -1.92779 -0.45410 C 0.62078 0.66339 -0.48948 C 0.05642 1.91772 -0.33331 C 0.79512 2.92161 0.50930 F 1.96223 3.23986 -0.05414 F -5.26417 -3.16210 -0.21554 F -5.81004 -1.08482 -0.18838 F -4.56134 -1.85358 -1.76107 F -2.27189 1.98842 2.15381 F -3.35309 0.88685 3.64108 F -1.20718 0.82682 3.61524 F 0.10831 4.03408 0.68736 F 1.07425 2.40993 1.71055 C -3.13018 1.55389 -2.30879 F -3.32301 0.86338 -3.42461 F -4.10341 1.21682 -1.45664 F -3.27230 2.83989 -2.58723 C 8.19485 -0.04168 -0.55913 C 6.83842 -1.29748 0.92000 C 8.06962 -0.77403 0.60974 H 5.06631 -0.17984 -1.76422 H 4.49545 -2.22114 1.39922 H 3.20447 -1.06843 -1.13735 H 2.31679 -2.75723 1.30212 H -0.16368 -2.34949 -1.86605 H 1.44004 -1.67477 -2.05633 H 0.34203 -3.41233 1.52119 H -0.35415 -3.91989 -0.02099 H 7.28102 0.76009 -2.31828 H -1.75079 -0.74774 -2.43518 H -2.55132 -3.29162 -0.53188 H -0.32942 -0.94056 2.27859 H -1.59149 3.20333 -0.80910 H -4.38069 0.07414 1.36228 H 1.56198 0.45177 0.00869 H 8.93355 -0.91596 1.24588 H 6.71465 -1.87409 1.83024 F 9.36258 0.46393 -0.86896 Iminium 54 M06/def2-TZVP Geometry C -6.86033 -1.40154 1.03340 C -5.77253 -1.15224 0.18715 C -4.51288 -1.73911 0.51702 C -3.33908 -1.63343 -0.16403 C -2.20366 -2.29258 0.33074 N -1.00407 -2.31829 -0.18061 C -0.64442 -1.62530 -1.42771 C 0.07326 -3.09386 0.46806 C -8.09969 -0.85851 0.76094 C -0.69524 0.66892 -0.38941 C -0.06293 -0.25447 -1.20473 C 2.34010 -0.43833 1.88930 C 1.24255 -1.24731 1.68830 C 1.28896 -2.26159 0.73722 C 2.44807 -2.46201 0.01436 C 1.04980 2.26750 -0.79173 C -0.13759 1.91817 -0.17824 C 3.50064 -0.62962 1.14817 C 3.55090 -1.64265 0.21558 C 4.77105 -1.87929 -0.63382 C 2.30225 0.69060 2.88499 C 1.12935 0.09634 -1.82089 C 1.67657 1.35088 -1.61903 C 3.00814 1.68850 -2.23747 F 3.13324 2.98817 -2.45228 F 3.38671 0.69742 3.64573 F 2.25215 1.86612 2.25226 F 1.24163 0.61578 3.67819 F 5.21626 -3.12332 -0.48265 F 4.46545 -1.72765 -1.92593 F 5.75476 -1.04862 -0.34464 F 4.00087 1.31794 -1.42221 F 3.18470 1.05729 -3.39033 C -0.86469 2.86765 0.73485 F -1.11287 2.28617 1.91113 F -0.18141 3.97359 0.96040 F -2.04574 3.20708 0.21611 C -8.27516 -0.06006 -0.35448 C -5.95308 -0.34233 -0.94289 C -7.19420 0.18534 -1.19016 H -6.71947 -2.02695 1.90753 H -4.50689 -2.33967 1.42577 H -3.27637 -1.04452 -1.07140 H -2.32123 -2.85842 1.25350 H -1.53231 -1.58765 -2.06165 H 0.08039 -2.25853 -1.94454 H 0.32179 -3.92740 -0.19557 H -0.33874 -3.51091 1.38943 H -8.93678 -1.05468 1.41846 H -1.62400 0.42372 0.11669 H 0.33940 -1.08204 2.26848 H 2.50164 -3.25564 -0.72605 H 1.48998 3.24160 -0.61976 H 4.35739 0.01590 1.30194 H 1.64582 -0.61537 -2.45713 F -7.36989 0.94833 -2.25147 H -5.14672 -0.11486 -1.62882 H -9.23519 0.38079 -0.59413 Iminium 55 M06/def2-TZVP Geometry C 6.94259 -1.12745 1.02016 C 5.86209 -0.97731 0.13102 C 4.60705 -1.54592 0.49060 C 3.41904 -1.53610 -0.17850 C 2.31770 -2.17910 0.40707 N 1.10826 -2.28319 -0.07111 C 0.70230 -1.71254 -1.36523 C 0.06505 -3.01644 0.67360 C 8.18131 -0.60396 0.74279 C 0.70120 0.66115 -0.52074 C 0.08621 -0.34363 -1.24767 C -3.44150 -1.62688 0.45643 C -2.33826 -2.45120 0.27669 C -1.14997 -2.17642 0.92337 C -1.07346 -1.08145 1.77785 C -1.10007 2.16821 -1.01776 C 0.10596 1.90516 -0.39887 C -3.36113 -0.53313 1.29062 C -2.17037 -0.26679 1.95735 C -2.10057 0.94397 2.85006 C -4.70078 -1.95730 -0.29950 C -1.12623 -0.08009 -1.86825 C -1.70908 1.16956 -1.75929 C -3.06303 1.41756 -2.36991 F -3.26565 0.65875 -3.43829 F -5.67413 -1.10009 -0.05505 F -4.46293 -1.95238 -1.61397 F -5.13010 -3.17681 0.01386 F -2.10056 2.06197 2.11938 F -3.14635 1.00284 3.66170 F -1.00104 0.94915 3.59207 F -4.02330 1.12985 -1.48519 F -3.21579 2.68345 -2.72525 C 0.79897 2.93312 0.45244 F 0.96279 2.46916 1.69449 F 2.01626 3.20005 -0.02293 F 0.12820 4.06712 0.52395 C 8.37895 0.09202 -0.44347 C 6.11194 -0.26697 -1.05424 C 7.34330 0.26287 -1.34739 H 6.77592 -1.67200 1.94321 H 4.61738 -2.06027 1.45124 H 3.32090 -1.03872 -1.13259 H 2.47064 -2.65440 1.37483 H -0.01619 -2.40751 -1.80620 H 1.57458 -1.70659 -2.02134 H 0.51475 -3.35710 1.60874 H -0.19735 -3.90135 0.08632 H 8.99692 -0.73164 1.44215 H 1.64450 0.48586 -0.01257 H -2.41522 -3.30815 -0.38706 H -0.14667 -0.85709 2.29781 H -1.56967 3.13829 -0.91394 H -4.21830 0.11586 1.42688 H -1.62959 -0.85660 -2.43534 F 5.12967 -0.09780 -1.92631 H 9.35297 0.50879 -0.66967 H 7.47764 0.80211 -2.27635 Iminium 56 M06/def2-TZVP Geometry C 6.53569 -1.46802 1.02541 C 5.43983 -1.22800 0.18162 C 4.18044 -1.78834 0.53021 C 2.99887 -1.68908 -0.14596 C 1.86150 -2.31347 0.37850 N 0.65332 -2.33623 -0.11935 C 0.29331 -1.68227 -1.38558 C -0.42749 -3.07387 0.56395 C 7.77735 -0.95238 0.74392 C -1.43916 0.07114 -1.83101 C -0.25357 -0.29089 -1.20623 C -2.69483 -0.35032 1.85557 C -1.59619 -1.16685 1.69296 C -1.64143 -2.22635 0.79230 C -2.80213 -2.46446 0.08361 C -1.29997 2.26975 -0.86724 C -1.95347 1.34387 -1.66422 C -3.85643 -0.57935 1.12671 C -3.90701 -1.63965 0.24824 C -5.13029 -1.92422 -0.58120 C -2.65540 0.82466 2.79630 C 0.40381 0.64025 -0.42080 C -0.12050 1.91003 -0.24697 C 0.63094 2.86479 0.63988 F 0.00357 4.01572 0.79065 F -1.61358 0.76695 3.61551 F -2.56702 1.96772 2.11013 F -3.75507 0.88983 3.53194 F -6.12862 -1.10691 -0.30260 F -5.54784 -3.17280 -0.39389 F -4.84110 -1.79852 -1.87965 F 0.81565 2.33127 1.84972 F 1.84299 3.11549 0.14048 C -3.27751 1.71333 -2.27993 F -3.55378 0.96656 -3.33962 F -4.26145 1.53526 -1.39308 F -3.30306 2.98448 -2.65086 C 7.94200 -0.17828 -0.39811 C 5.63810 -0.44118 -0.96586 C 6.87221 0.07941 -1.25480 H 6.39588 -2.07239 1.91528 H 4.17010 -2.36432 1.45505 H 2.93578 -1.12705 -1.07021 H 1.97886 -2.85153 1.31767 H -0.45258 -2.31643 -1.87047 H 1.17337 -1.68822 -2.03180 H -0.01907 -3.44802 1.50516 H -0.68122 -3.93804 -0.05757 H 8.62285 -1.13738 1.39363 H -1.97575 -0.64734 -2.44252 H -0.69283 -0.97305 2.26393 H -2.85643 -3.29515 -0.61484 H -1.71675 3.25892 -0.72384 H -4.71458 0.07061 1.25099 H 1.32653 0.38623 0.09175 H 4.81316 -0.23290 -1.63680 Cl 9.48002 0.47206 -0.76178 H 7.03107 0.68794 -2.13574 Iminium 57 M06/def2-TZVP Geometry C 5.95448 -1.59032 1.18977 C 4.88242 -1.33435 0.32084 C 3.60677 -1.87549 0.64047 C 2.44197 -1.75409 -0.06063 C 1.28394 -2.36462 0.43418 N 0.08670 -2.36465 -0.09017 C -0.23552 -1.69256 -1.35709 C -1.01886 -3.09441 0.56158 C 7.21052 -1.09351 0.93592 C -1.92743 0.09435 -1.82567 C -0.76476 -0.29462 -1.17454 C -3.28220 -0.35449 1.82448 C -2.19050 -1.18370 1.68069 C -2.22750 -2.23416 0.76910 C -3.37312 -2.45001 0.02939 C -1.78348 2.27560 -0.82412 C -2.42854 1.37155 -1.65220 C -4.42858 -0.56191 1.06570 C -4.47088 -1.61223 0.17484 C -5.67476 -1.86842 -0.69152 C -3.24920 0.81351 2.77405 C -0.11456 0.61551 -0.35900 C -0.62496 1.89019 -0.18022 C 0.11818 2.82266 0.73669 F -0.50033 3.97762 0.89342 F -2.22675 0.73748 3.61582 F -3.13078 1.95974 2.09725 F -4.36425 0.88836 3.48514 F -6.67080 -1.04409 -0.42558 F -6.11151 -3.11495 -0.53776 F -5.34918 -1.72338 -1.97955 F 1.34243 3.06846 0.26560 F 0.27302 2.26818 1.94125 C -3.73185 1.76805 -2.29462 F -3.73500 3.04683 -2.63917 F -3.98758 1.04662 -3.37676 F -4.74060 1.58189 -1.43767 C 7.41461 -0.32422 -0.20265 C 5.11908 -0.55260 -0.82248 C 6.36843 -0.05219 -1.08327 H 5.78493 -2.19124 2.07691 H 3.56724 -2.45467 1.56253 H 2.40787 -1.18572 -0.98251 H 1.37256 -2.91192 1.37116 H -0.98053 -2.30987 -1.86453 H 0.65816 -1.70578 -1.98422 H -0.63698 -3.48132 1.50877 H -1.26831 -3.95025 -0.07305 H 8.03416 -1.29343 1.60917 H -2.45648 -0.60589 -2.46423 H -1.29839 -1.00621 2.27424 H -3.42050 -3.27266 -0.67900 H -2.19015 3.26823 -0.67605 H -5.28177 0.09686 1.17659 H 0.79077 0.34062 0.17342 H 4.31343 -0.33291 -1.51304 Br 9.11472 0.35947 -0.56279 H 6.55130 0.55124 -1.96317 Iminium 58 M06/def2-TZVP Geometry N -0.03030 1.81924 0.15224 C 0.63549 0.72706 -0.03455 C -1.50263 1.95568 0.24932 C -2.22057 0.65689 0.11540 C -2.61618 0.20180 -1.13671 C -3.25688 -1.01797 -1.26397 C -3.50400 -1.78937 -0.14012 C -3.11367 -1.34124 1.11138 C -2.47322 -0.12149 1.23881 C 2.05403 0.65207 -0.11859 C 2.55061 -0.58907 -0.32523 C 2.85447 1.90475 0.01721 C 3.95628 -1.00838 -0.45347 C 4.27617 -2.18263 0.46516 H 0.49432 2.68352 0.24345 H 0.04424 -0.18139 -0.13015 H -1.80049 2.66038 -0.53152 H -1.70628 2.42819 1.21385 H -2.43402 0.81443 -2.01473 H -3.57457 -1.36220 -2.24050 H -4.01359 -2.74015 -0.23879 H -3.31955 -1.93811 1.99138 H -2.17915 0.23831 2.22042 H 1.82590 -1.40014 -0.40167 H 2.66394 2.39804 0.97518 H 3.92292 1.71375 -0.03684 H 2.61661 2.61669 -0.77900 H 4.64449 -0.17916 -0.28352 H 4.10451 -1.32522 -1.49485 H 5.30360 -2.51156 0.31619 H 4.15957 -1.90721 1.51413 H 3.62023 -3.03160 0.26346 Cartesian coordinates of reaction components for predicting gold catalyzed dearomatization Gold intermediate 1 M06/def2-TZVP Geometry C -0.78726 -3.36224 1.99169 C -0.87123 -2.35379 1.09910 C -2.15110 -2.30669 0.47226 N -2.64408 -1.34165 -0.25559 C -2.04894 -0.04627 -0.42177 S -4.24057 -1.58517 -1.05450 C -1.45892 0.29780 -1.62572 C -0.93089 1.56918 -1.76987 C -1.00820 2.47895 -0.72829 C -1.60993 2.12370 0.46934 C -2.13472 0.85478 0.62892 O -3.98505 -1.30323 -2.41971 O -4.65383 -2.86264 -0.59186 C -5.16151 -0.31168 -0.31958 C -5.71594 -0.52044 0.93748 C -6.40709 0.51023 1.53592 C -6.55600 1.74249 0.89939 C -5.98725 1.92055 -0.35904 C -5.28756 0.90437 -0.97658 C -7.34035 2.83402 1.54254 P 2.64308 0.16630 0.05459 C 2.45291 0.89794 -1.59627 C 2.95417 1.55296 1.17609 C 2.13466 0.04327 -2.64987 C 1.97010 0.54163 -3.92787 C 2.10815 1.90247 -4.16349 C 2.41717 2.75724 -3.12003 C 2.59283 2.25820 -1.83788 C 4.22445 2.10081 1.32439 C 4.41404 3.19752 2.14617 C 3.33993 3.75449 2.82117 C 2.07375 3.21145 2.68005 C 1.88156 2.11076 1.86416 H -1.62547 -4.02653 2.20565 H 0.11591 -3.55613 2.55980 H -1.40827 -0.42555 -2.43053 H -0.44887 1.84582 -2.70040 H -0.59133 3.47201 -0.85009 H -1.67117 2.83761 1.28218 H -2.61170 0.55448 1.55595 H -5.61458 -1.48249 1.42639 H -6.85203 0.36117 2.51362 H -6.09918 2.87452 -0.86219 H -4.84392 1.04206 -1.95527 H -7.03392 3.81634 1.18290 H -8.40367 2.72090 1.31310 H -7.24284 2.81177 2.62850 H 2.02099 -1.02164 -2.46463 H 1.73436 -0.13084 -4.74410 H 1.97894 2.29426 -5.16538 H 2.53196 3.81902 -3.30324 H 2.83927 2.93421 -1.02607 H 5.06922 1.66638 0.79989 H 5.40576 3.61761 2.26257 H 3.49295 4.61088 3.46697 H 1.23582 3.63929 3.21781 H 0.89309 1.67170 1.76225 H 3.65377 -1.92898 1.71774 C 6.34906 -1.24694 -0.95465 C 6.57035 -2.19729 0.02750 C 5.60439 -2.43951 0.99087 C 4.41566 -1.73433 0.96851 C 4.18860 -0.77470 -0.01365 C 5.16275 -0.53403 -0.97683 H 7.10337 -1.05887 -1.70914 H 7.49877 -2.75551 0.04048 H 5.77565 -3.18535 1.75757 H 4.99531 0.21005 -1.74840 H -2.81819 -3.16763 0.56047 Au 0.76401 -1.12526 0.63083 Gold intermediate 2 M06/def2-TZVP Geometry C -0.77987 0.29683 -2.04263 C -0.59405 1.10770 -3.10725 C -2.10129 -0.22738 -2.01280 N -2.72818 -0.77808 -1.00676 C -2.29536 -0.76248 0.35947 S -4.39220 -1.41273 -1.28162 O -4.36227 -2.72526 -0.74783 O -4.63259 -1.14481 -2.65537 C -5.30152 -0.34595 -0.25643 C -5.61891 0.92394 -0.72273 C -6.29791 1.78570 0.11062 C -6.66702 1.39971 1.39918 C -6.33238 0.12144 1.83763 C -5.64897 -0.75746 1.02217 C -7.43697 2.32840 2.27401 C -2.24546 0.45701 1.01908 C -1.97816 0.47996 2.37505 C -1.77103 -0.70680 3.06032 C -1.80247 -1.91701 2.38670 C -2.06638 -1.95367 1.02872 P 2.89288 -0.80389 0.23803 C 4.01557 0.56869 0.70868 C 2.55043 -1.76540 1.81682 C 3.83282 -1.79304 -1.07342 C 2.84090 -2.68616 -1.81906 C 4.37723 -0.76065 -2.05920 C 4.97102 -2.67574 -0.57915 C 1.72105 -0.81938 2.68115 C 3.75759 -2.20946 2.63317 C 1.71330 -2.98983 1.46223 C 3.70958 1.92405 0.50221 C 4.69284 2.88162 0.75581 C 5.94442 2.54026 1.22374 C 6.24135 1.20999 1.45427 C 5.28782 0.24755 1.19329 C 2.40677 2.47417 0.04907 C 1.30764 2.51692 0.90215 C 0.15086 3.17990 0.52792 C 0.07073 3.80428 -0.70510 C 1.15704 3.76410 -1.56376 C 2.31694 3.10866 -1.18716 H -1.39048 1.33733 -3.81658 H 0.35667 1.59292 -3.30028 H -2.69366 -0.21336 -2.93054 H -5.34706 1.22006 -1.72958 H -6.56005 2.77745 -0.24136 H -6.61729 -0.18868 2.83686 H -5.38976 -1.75263 1.36236 H -8.50759 2.24092 2.06857 H -7.29012 2.10190 3.33011 H -7.16072 3.36838 2.09668 H -2.43762 1.37204 0.46819 H -1.94589 1.42630 2.90173 H -1.57494 -0.68737 4.12576 H -1.62715 -2.84244 2.92183 H -2.11619 -2.89279 0.49244 H 3.38135 -3.22249 -2.60468 H 2.04627 -2.10799 -2.29539 H 2.37648 -3.43315 -1.17397 H 3.59372 -0.08038 -2.40923 H 5.18414 -0.16221 -1.63264 H 4.77345 -1.28470 -2.93376 H 5.43531 -3.15267 -1.44775 H 4.61923 -3.47716 0.07321 H 5.75814 -2.12342 -0.06723 H 0.81493 -0.48543 2.16897 H 1.41851 -1.34345 3.59383 H 2.29677 0.06052 2.98101 H 4.44027 -2.85337 2.07858 H 4.31771 -1.36337 3.03180 H 3.39506 -2.78544 3.49032 H 2.29954 -3.74919 0.94068 H 1.34429 -3.44503 2.38674 H 0.84725 -2.73406 0.84453 H 4.44554 3.92446 0.59028 H 6.68142 3.31110 1.41390 H 7.21454 0.91736 1.82908 H 5.55248 -0.78595 1.36370 H 1.37491 2.05300 1.88085 H -0.68542 3.22643 1.21671 H -0.82876 4.33719 -0.99034 H 1.10913 4.26349 -2.52480 H 3.17791 3.09948 -1.84822 Au 0.84920 -0.16325 -0.80079 Gold intermediate 3 M06/def2-TZVP Geometry C -0.86394 1.38979 2.05446 C -0.65097 1.91399 3.23725 C -1.71576 1.25565 0.98816 N -2.64544 0.29077 0.85305 S -3.05193 -0.20612 -0.74745 O -2.50049 -1.51245 -0.89804 O -2.63751 0.87643 -1.57570 C -4.79073 -0.30495 -0.67506 C -5.53540 0.86877 -0.65831 C -6.90860 0.78445 -0.61791 C -7.55567 -0.45210 -0.59943 C -6.78534 -1.60867 -0.62019 C -5.40495 -1.54681 -0.65773 C -9.04476 -0.51552 -0.57745 P 2.35876 -1.07781 0.00870 C 3.58238 -0.14986 -0.98329 C 3.28102 -1.84689 1.46365 C 1.55945 -2.31263 -1.15847 C 2.53330 -3.19447 -1.92989 C 0.59462 -3.19124 -0.37066 C 0.77140 -1.47706 -2.16555 C 4.09924 -3.09481 1.15650 C 2.26300 -2.20822 2.54583 C 4.19366 -0.75248 2.01211 C 3.45614 1.21632 -1.27833 C 4.46464 1.84133 -2.01065 C 5.57591 1.15468 -2.45458 C 5.69972 -0.19359 -2.17313 C 4.71295 -0.82923 -1.44845 C 2.32205 2.09469 -0.88672 C 1.21110 2.22722 -1.71361 C 0.22127 3.15223 -1.42030 C 0.33065 3.95479 -0.29612 C 1.43041 3.82605 0.53730 C 2.42315 2.90689 0.24034 H -1.40383 2.52498 3.72827 H 0.28066 1.76973 3.77153 H -1.61314 1.92943 0.13765 H -5.03806 1.83143 -0.68793 H -7.50223 1.69232 -0.60649 H -7.27670 -2.57515 -0.61068 H -4.80447 -2.44794 -0.68556 H -9.45720 -0.17785 -1.53172 H -9.45541 0.13867 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-2.23140 -2.32111 H 5.69093 2.31594 1.18241 H 1.57426 2.44847 2.35945 H 3.92506 3.14250 2.71577 H 6.01457 1.55953 -1.21448 H 6.53128 -0.51337 -2.14962 H 1.94792 -1.22144 1.73710 H 1.33893 3.13105 -0.54128 H 1.01677 -3.31072 2.53663 H -2.89452 -2.17306 1.20493 H -3.47748 2.14974 -1.16553 H -0.10285 4.72672 -1.70232 H -1.42427 -3.78678 2.29821 H -2.52759 4.23349 -2.01181 H -4.25822 1.20277 1.52866 H -7.34785 -0.88447 -0.56761 H -3.24799 -1.45894 -1.64725 H -6.62265 1.82322 1.84835 H -7.90153 0.99651 0.94877 H -7.15641 0.21983 2.34336 H -5.20031 -3.16466 -2.25495 H -6.82404 -2.46445 -2.26234 H -5.56208 -1.80289 -3.30540 Cartesian coordinates of reaction components relevant to secondary amine catalysis Carbonyl 1 M06-2X/def2-TZVP Geometry C 2.41641 -0.16193 -0.00000 C 1.03252 0.38970 -0.00000 C -0.08691 -0.32977 -0.00000 C -1.39907 0.33121 0.00000 O -2.45235 -0.24995 0.00000 H 2.96630 0.18771 0.87644 H 2.41221 -1.25048 -0.00000 H 2.96630 0.18771 -0.87644 H 0.94032 1.47431 0.00000 H 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0.31891 C 2.24634 -0.24634 -0.30709 C 1.13175 -0.10439 0.40688 O 4.61193 -0.17561 -0.25979 C -0.25985 -0.24178 -0.10862 C -1.05934 1.05346 0.05671 H 3.53395 0.18896 1.39776 H 2.23275 -0.49792 -1.36207 H 1.23004 0.15263 1.46141 H -0.56406 1.85466 -0.49587 H -0.76958 -1.04095 0.43903 H -0.24172 -0.53483 -1.16103 H -1.05740 1.35025 1.11018 C -2.50514 0.91346 -0.42989 C -3.29678 -0.05411 0.39475 C -3.85095 -1.16730 -0.06114 H -3.39809 0.19433 1.44925 H -4.40912 -1.83100 0.58618 H -2.51323 0.59657 -1.47609 H -2.98276 1.89636 -0.38815 H -3.76928 -1.44863 -1.10528 Carbonyl 137 M06-2X/def2-TZVP Geometry C 3.86706 0.11215 0.00002 C 2.40904 0.26924 -0.00002 C 1.61958 -0.80847 0.00004 O 4.64757 1.02867 -0.00004 C 0.15701 -0.84808 0.00002 C -0.47564 -2.08602 0.00000 C -1.86463 -2.15987 -0.00002 C -2.62425 -1.00951 -0.00003 C -1.99599 0.24055 -0.00001 C -0.61295 0.32266 0.00002 O -2.82338 1.31168 -0.00001 H 4.22374 -0.93747 0.00008 H 2.03637 1.28630 -0.00009 H 2.10489 -1.78234 0.00010 H 0.11950 -2.99022 0.00001 H -2.35467 -3.12457 -0.00004 H -0.12089 1.28356 0.00004 H -3.70550 -1.04099 -0.00004 C -2.24132 2.59650 0.00002 H -1.62897 2.75243 -0.89210 H -3.06639 3.30311 0.00001 H -1.62899 2.75241 0.89216 Dialdehyde M06-2X/def2-TZVP Geometry C -0.36826 0.66100 0.00021 C 0.36826 -0.66100 0.00024 C -1.86133 0.50143 0.00034 C 1.86133 -0.50143 0.00016 O 2.42707 0.55705 -0.00034 O -2.42708 -0.55705 -0.00039 H -0.09041 1.27029 -0.86556 H -0.09030 1.27039 0.86587 H 0.09031 -1.27039 -0.86542 H 0.09041 -1.27029 0.86601 H -2.43922 1.44555 -0.00056 H 2.43922 -1.44555 -0.00023 Ketone OH M06-2X/def2-TZVP Geometry C -1.83748 -0.46026 0.01846 C -0.47067 0.16322 -0.01714 C 0.72115 -0.77081 -0.03638 O 1.92488 -0.07689 0.04071 O -0.29239 1.35577 -0.01501 H -2.06613 -0.72967 1.05221 H -2.58048 0.25227 -0.33016 H -1.87174 -1.37334 -0.57589 H 0.62081 -1.47565 0.79831 H 0.66194 -1.36229 -0.96007 H 1.69766 0.86472 0.02040 Dihydroxyacetone 1 M06-2X/def2-TZVP Geometry C -0.29936 1.28948 0.11673 C 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1.49580 -1.14800 -0.58376 O 3.73817 -0.28791 -0.39846 O 0.78187 0.64843 1.16231 C -0.25577 0.19785 0.30814 O 0.29841 -0.44366 -0.83276 C -1.08940 1.35960 -0.21535 C -1.10173 -0.76841 1.12622 C -2.29406 0.86675 -1.01460 C -3.14609 -0.08525 -0.17854 C -2.31020 -1.25691 0.33192 H 2.64237 1.45317 1.24115 H 1.76152 1.84618 -0.24856 H 1.78136 -1.65559 -1.50283 H 1.38774 -1.89495 0.21142 H -1.42199 1.93385 0.65302 H -0.45610 2.00651 -0.82512 H -0.47511 -1.60088 1.45239 H -1.42181 -0.23973 2.02772 H -2.88741 1.71971 -1.34785 H -1.94055 0.34949 -1.91002 H -3.56400 0.45926 0.67526 H -3.99000 -0.45189 -0.76550 H -1.96177 -1.84775 -0.51951 H -2.91585 -1.91728 0.95451 Cyclopentadiene M06/def2-TZVP Geometry C -1.16941 0.28067 0.00000 C -0.72913 -0.98349 -0.00000 C 0.72911 -0.98350 -0.00000 C 1.16942 0.28065 0.00000 C 0.00001 1.20527 0.00001 H 1.34407 -1.87389 -0.00001 H 2.19963 0.60781 0.00000 H 0.00002 1.86728 0.87460 H -1.34410 -1.87387 -0.00001 H -2.19962 0.60785 0.00000 H 0.00002 1.86729 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-0.52702 -1.00833 C 2.44284 -0.49769 0.21626 C 2.59853 0.60769 1.04087 C 3.40210 1.66507 0.64913 H 4.68016 2.45589 -0.87901 H 4.40759 0.49595 -2.36003 H 2.97853 -1.39212 -1.65373 H 2.07235 0.63793 1.98862 H 3.51892 2.52367 1.29999 Diene 3 M06/def2-TZVP Geometry C -1.77818 1.64665 -0.39091 C -1.29149 0.47379 0.01845 C -2.18437 -0.58852 0.50216 C -3.35690 -0.89933 -0.03216 H -1.82425 -1.15956 1.35620 H -1.13779 2.41891 -0.79978 H -2.83701 1.86572 -0.32819 H -3.72678 -0.39263 -0.91742 H -3.98346 -1.67646 0.38771 C 2.89250 -0.39012 -0.03669 C 1.96635 -1.39736 -0.24456 C 0.61260 -1.11420 -0.21344 C 0.15617 0.18232 0.01530 C 1.10106 1.18314 0.23398 C 2.45357 0.90169 0.20516 H 3.95323 -0.61136 -0.05521 H 2.29939 -2.41133 -0.43409 H -0.10755 -1.90629 -0.39021 H 0.76505 2.19067 0.45302 H 3.17138 1.69396 0.38425 Diene 4 M06/def2-TZVP Geometry C -1.44139 1.36871 -0.09029 C -1.08639 0.08681 -0.05750 C 0.29938 -0.35677 -0.22963 C 1.38279 0.28036 0.20117 H 0.43071 -1.31861 -0.72836 H -2.47081 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H -0.76459 -1.79374 -1.54256 C -1.57428 -1.06235 1.53414 H -1.48905 -0.44749 2.43254 H -2.52108 -1.60547 1.59022 H -0.76458 -1.79368 1.54263 C -2.88072 1.24984 -0.00001 H -2.82067 1.88849 0.88331 H -2.82068 1.88846 -0.88335 H -3.86024 0.76611 0.00000 H 3.09873 -1.94900 0.00001 Furan 3 M06/def2-TZVP Geometry C -2.15300 0.04201 0.00000 C -2.38051 1.37196 -0.00001 C -1.10767 2.02482 -0.00001 C -0.19341 1.02950 -0.00001 O -0.79735 -0.18135 -0.00000 H -3.34981 1.84517 -0.00001 H -0.89622 3.08039 -0.00001 O 1.12374 1.04912 -0.00001 Si 2.20447 -0.23216 -0.00000 C 1.96954 -1.25468 1.53366 H 2.73541 -2.03252 1.58906 H 2.05314 -0.64009 2.43241 H 0.99315 -1.74153 1.54228 C 1.96954 -1.25470 -1.53365 H 0.99315 -1.74155 -1.54226 H 2.05315 -0.64012 -2.43241 H 2.73541 -2.03254 -1.58904 C 3.85635 0.61198 -0.00000 H 3.97398 1.24265 -0.88328 H 3.97398 1.24266 0.88327 H 4.66523 -0.12231 -0.00000 C -3.01378 -1.15955 0.00001 H -2.77412 -1.77955 0.87272 H -2.77413 -1.77955 -0.87270 C -4.48785 -0.81473 0.00001 H -5.10059 -1.71642 0.00001 H -4.75529 -0.22813 0.88171 H -4.75529 -0.22813 -0.88170 Furan 4 M06/def2-TZVP Geometry C -2.43267 -0.76327 -0.21027 C -2.45707 -2.09121 -0.49870 C -1.11728 -2.53736 -0.54117 C -0.35969 -1.43351 -0.27070 O -1.13077 -0.35685 -0.06988 H -3.35066 -2.67231 -0.66126 H -0.74389 -3.52714 -0.74027 O 0.93085 -1.26753 -0.17917 Si 1.74784 0.19526 0.12065 C 1.30440 0.84948 1.83718 H 2.27060 1.20430 2.22977 C 0.33598 2.02664 1.84686 C 0.79902 -0.24895 2.76927 C 3.54536 -0.35433 0.08904 C 3.85370 -1.34871 1.20293 C 3.97274 -0.92593 -1.25675 H 4.12557 0.56071 0.28006 C 1.31584 1.42214 -1.23762 C 2.35942 2.53441 -1.28802 C 1.11224 0.80149 -2.61348 H 0.36053 1.86462 -0.92721 C -3.44236 0.25851 -0.03347 O -3.22412 1.41303 0.22446 O -4.67341 -0.25678 -0.19739 C -5.73553 0.66845 -0.04272 H -5.65836 1.47799 -0.77075 H -6.65410 0.10853 -0.20312 H -5.73244 1.10412 0.95805 H 0.17814 2.37822 2.87138 H 0.70143 2.87616 1.26520 H -0.64169 1.74804 1.44399 H 0.70389 0.12966 3.79144 H -0.19353 -0.59063 2.46250 H 1.45273 -1.12348 2.79770 H 2.04389 3.33639 -1.96205 H 2.54230 2.98561 -0.30738 H 3.31923 2.16183 -1.65925 H 2.02270 0.32351 -2.98448 H 0.32353 0.04598 -2.61576 H 0.83157 1.56906 -3.34175 H 3.34968 -1.78138 -1.53525 H 3.90686 -0.19225 -2.06279 H 5.00872 -1.27753 -1.21783 H 4.90773 -1.64254 1.17735 H 3.65098 -0.94245 2.19641 H 3.25991 -2.26077 1.08776 Furan 5 M06/def2-TZVP Geometry C 2.34315 -0.85419 -0.00840 C 2.82222 0.40338 0.07366 C 1.71387 1.30578 -0.04535 C 0.63587 0.50267 -0.19562 O 0.98411 -0.80730 -0.17880 H 3.85977 0.67131 0.20775 C 1.72392 2.78871 -0.01755 O -0.64255 0.78867 -0.37787 H 2.56841 -2.78431 0.88140 C 2.95753 -2.19154 0.04844 H 2.77936 -2.76091 -0.86824 H 4.03481 -2.09112 0.18005 Si -1.97162 -0.14624 0.02869 C -2.12532 -1.57813 -1.14485 H -3.04059 -2.13983 -0.94126 H -2.16807 -1.23396 -2.18031 H -1.27913 -2.26001 -1.04741 C -1.78684 -0.73256 1.78328 H -1.62454 0.10695 2.46274 H -2.68921 -1.25650 2.10780 H -0.94529 -1.42017 1.88496 C -3.39989 1.02301 -0.16022 H -3.30937 1.87066 0.52157 H -3.45175 1.41269 -1.17881 H -4.34383 0.51631 0.05362 H 2.13884 3.17532 0.91734 H 2.32308 3.20694 -0.83112 H 0.71072 3.18016 -0.11867 5-methyl furan M06/def2-TZVP Geometry O 1.03051 -0.23913 0.00000 C 0.49667 -1.48361 0.00000 C -0.85029 -1.41815 0.00000 C -1.17486 -0.02991 0.00000 C -0.00000 0.64113 0.00000 C 0.34969 2.07314 0.00000 H 1.19821 -2.30158 0.00000 H -1.53218 -2.25298 0.00000 H -2.15712 0.41565 0.00000 H -0.55806 2.67574 0.00000 H 0.93890 2.34032 0.88091 H 0.93890 2.34032 -0.88091 5-methoxy furan M06/def2-TZVP Geometry O -0.17242 -0.92546 0.00005 C -1.54226 -0.98369 0.00002 C -2.05077 0.26360 -0.00007 C -0.94641 1.16657 -0.00009 C 0.15405 0.37572 -0.00001 O 1.43947 0.70250 0.00001 C 2.38086 -0.35068 0.00007 H -1.96883 -1.97137 0.00006 H -3.09773 0.52105 -0.00011 H -0.95867 2.24283 -0.00015 H 3.36191 0.11923 0.00008 H 2.27702 -0.97860 0.88875 H 2.27706 -0.97866 -0.88858 5-methoxy thiophene M06/def2-TZVP Geometry C -1.90786 -0.60265 0.00006 C -1.98240 0.75186 0.00001 C -0.72091 1.38917 -0.00009 C 0.30493 0.49425 -0.00007 O 1.60285 0.82146 -0.00019 C 2.53534 -0.22926 0.00003 H -2.70731 -1.32637 0.00012 H -2.92178 1.28912 0.00000 H -0.55884 2.45801 -0.00017 H 3.52500 0.22310 -0.00016 H 2.42680 -0.85668 0.89234 H 2.42670 -0.85714 -0.89195 S -0.27425 -1.14512 0.00011 Aromatic amine 1 M06/def2-TZVP Geometry C 0.74269 1.52603 -0.01319 C -0.54106 2.02328 0.00296 C -1.65509 1.19685 0.00551 C -1.44528 -0.17545 -0.00618 C -0.15959 -0.69920 -0.02177 C 0.95841 0.13624 -0.03155 N 2.23117 -0.38490 -0.06047 O -2.43900 -1.09522 -0.00115 C -3.76221 -0.63689 0.01828 C 3.36811 0.48982 0.03843 C 2.42302 -1.80738 0.01947 H 1.57671 2.21395 -0.01131 H -0.68517 3.09808 0.01593 H -2.64869 1.62207 0.01945 H -0.06748 -1.77691 -0.02607 H -4.39972 -1.51976 0.02017 H -3.97464 -0.04415 0.91544 H -3.99664 -0.03223 -0.86535 H 3.39579 1.21409 -0.78296 H 3.38592 1.05456 0.98010 H 4.28081 -0.10085 -0.01489 H 1.93481 -2.32854 -0.81140 H 3.48704 -2.03095 -0.03134 H 2.03116 -2.23310 0.95300 Aromatic amine 2 M06/def2-TZVP Geometry C 1.25008 -1.19668 0.09842 C 2.63130 -1.18657 0.09685 C 3.33908 -0.00004 0.00040 C 2.63140 1.18651 -0.09648 C 1.25018 1.19665 -0.09888 C 0.52626 -0.00000 -0.00044 N -0.84224 0.00003 -0.00092 C -1.64640 1.20287 0.02679 C -3.04257 0.68664 0.32617 C -3.04283 -0.68664 -0.32533 C -1.64644 -1.20279 -0.02697 H 0.72506 -2.13966 0.18836 H 3.16276 -2.12857 0.17694 H 4.42188 -0.00006 0.00073 H 0.72523 2.13963 -0.18922 H -1.28739 1.90168 0.79031 H -1.61263 1.73329 -0.93769 H -3.17450 0.58568 1.40756 H -3.82628 1.34727 -0.04518 H -3.82624 -1.34727 0.04666 H -3.17556 -0.58573 -1.40663 H -1.28819 -1.90216 -0.79031 H -1.61182 -1.73251 0.93789 H 3.16293 2.12849 -0.17626 Aromatic amine 3 M06/def2-TZVP Geometry C 0.13336 1.71540 -0.08588 C 1.46974 2.04537 -0.09508 C 2.46914 1.08359 -0.04625 C 2.08788 -0.25076 0.01406 C 0.74632 -0.60698 0.02686 C -0.25330 0.36508 -0.02357 N -1.57417 0.01225 -0.01362 O 2.95843 -1.28653 0.06881 C 4.32859 -0.99806 0.06708 C -2.03876 -1.35757 -0.05853 C -3.52744 -1.21640 -0.32023 C -3.86930 0.09409 0.36978 C -2.66280 0.96355 0.06277 H -0.61397 2.49611 -0.14030 H 1.75117 3.09147 -0.14677 H 3.50883 1.37891 -0.05687 H 0.50810 -1.66111 0.09007 H 4.84997 -1.95287 0.11684 H 4.63369 -0.47495 -0.84656 H 4.61822 -0.39062 0.93227 H -1.52701 -1.92240 -0.84522 H -1.84485 -1.87931 0.89160 H -3.70646 -1.12881 -1.39603 H -4.10350 -2.06666 0.04550 H -4.80621 0.53625 0.03025 H -3.94547 -0.06300 1.44987 H -2.48055 1.71288 0.84044 H -2.79077 1.50673 -0.88631 Aromatic amine 4 M06/def2-TZVP Geometry C -0.54640 1.19905 -0.01516 C -1.92769 1.18895 0.00771 C -2.63635 -0.00000 0.01809 C -1.92769 -1.18895 0.00771 C -0.54639 -1.19905 -0.01516 C 0.18120 0.00000 -0.03370 N 1.55793 0.00000 -0.07149 C 2.27621 1.24124 0.02830 C 2.27621 -1.24124 0.02830 H -0.03068 2.15015 -0.01858 H -2.45729 2.13525 0.02030 H -3.71896 -0.00000 0.03754 H -0.03068 -2.15015 -0.01858 H 2.02221 1.92309 -0.79064 H 2.08017 1.76875 0.97179 H 3.34505 1.04383 -0.02971 H 2.02221 -1.92309 -0.79064 H 3.34505 -1.04383 -0.02971 H 2.08017 -1.76875 0.97179 H -2.45729 -2.13525 0.02030 Aromatic amine 5 M06/def2-TZVP Geometry C -1.00482 2.26331 -0.65324 C -0.99409 3.64510 -0.65256 C 0.00090 4.35239 0.00003 C 0.99556 3.64464 0.65263 C 1.00562 2.26284 0.65335 C 0.00022 1.53909 0.00008 N -0.00009 0.15547 0.00008 C 0.81929 -0.60354 0.90606 C -0.81964 -0.60320 -0.90603 H -1.81938 1.74280 -1.14217 H -1.79012 4.17509 -1.16367 H 0.00117 5.43519 0.00001 H 1.81994 1.74196 1.14228 H 0.92907 -0.05057 1.84601 H 0.27125 -1.51579 1.17564 H -0.27182 -1.51554 -1.17576 H -0.92929 -0.05005 -1.84589 H 1.79186 4.17426 1.16372 C 4.71145 -1.75714 -0.50035 C 3.91994 -0.92971 -1.27574 C 2.66205 -0.54958 -0.83364 C 2.18250 -0.99350 0.38848 C 2.98428 -1.82617 1.16088 C 4.23897 -2.20556 0.72361 H 5.69449 -2.05372 -0.84672 H 4.28246 -0.57327 -2.23312 H 2.04521 0.10481 -1.44092 H 2.61272 -2.18124 2.11848 H 4.85167 -2.85571 1.33757 C -4.71202 -1.75627 0.50024 C -3.92034 -0.92912 1.27575 C -2.66238 -0.54917 0.83371 C -2.18293 -0.99298 -0.38850 C -2.98487 -1.82538 -1.16101 C -4.23963 -2.20459 -0.72380 H -5.69512 -2.05271 0.84657 H -4.28277 -0.57278 2.23320 H -2.04538 0.10497 1.44109 H -2.61338 -2.18038 -2.11867 H -4.85246 -2.85453 -1.33785 Aromatic amine 6 M06/def2-TZVP Geometry C -0.09647 1.22731 -0.04337 C -0.16173 2.60873 -0.18359 C 0.96087 3.41281 -0.11769 C 2.18679 2.81605 0.11037 C 2.28927 1.44270 0.21558 C 1.16651 0.61241 0.10502 H -1.14227 3.05947 -0.30047 H 0.87328 4.48790 -0.21320 H 3.26694 1.00388 0.36411 H 3.08285 3.42076 0.19387 N 1.31115 -0.76452 0.14108 C 2.59587 -1.36695 0.44585 C 2.34414 -2.84538 0.24984 C 1.44196 -2.83898 -0.97193 C 0.51570 -1.66478 -0.70056 H 3.38295 -1.03043 -0.24998 H 2.92130 -1.10444 1.45718 H 3.26353 -3.41572 0.11496 H 1.81202 -3.25461 1.11383 H 2.04167 -2.65034 -1.86768 H 0.89823 -3.77145 -1.12562 H -0.39398 -1.99662 -0.18678 H 0.19657 -1.15765 -1.61673 C -3.81726 -0.85293 0.26494 C -3.51939 -0.12862 -0.87677 C -2.31065 0.53823 -0.98145 C -1.37434 0.48597 0.04603 C -1.69067 -0.23717 1.19305 C -2.89950 -0.90023 1.30220 H -4.76282 -1.37575 0.34853 H -4.23136 -0.08396 -1.69306 H -2.07331 1.09829 -1.88051 H -0.97117 -0.27761 2.00415 H -3.12912 -1.45511 2.20481 Aromatic amine 7 M06/def2-TZVP Geometry C -0.39275 0.93513 -0.03792 C -1.74339 1.16211 0.07335 C -2.61735 0.07764 0.09967 C -2.12135 -1.21114 0.01379 C -0.75747 -1.45547 -0.09998 C 0.09963 -0.36865 -0.13646 H -2.12511 2.17507 0.15086 H -3.68358 0.24247 0.19559 H -0.38278 -2.47098 -0.15487 H -2.80645 -2.05084 0.04595 N 1.48177 -0.35714 -0.27344 C 0.77086 1.87885 -0.12076 C 1.94480 0.95055 0.17653 H 2.14798 0.92300 1.26160 H 2.87147 1.23036 -0.33018 C 2.25468 -1.49474 0.13224 H 3.30600 -1.32386 -0.10686 H 2.17416 -1.69365 1.21372 H 1.93462 -2.38895 -0.40513 H 0.85503 2.29304 -1.13204 H 0.71035 2.71864 0.57267 Aromatic amine 8 M06/def2-TZVP Geometry C 0.38980 -0.18396 -0.08160 C 1.42491 0.77583 0.06602 C 1.09899 2.14615 0.15472 C -0.20097 2.54582 0.08927 C -1.23572 1.60155 -0.02116 C -0.96896 0.25611 -0.08306 C 2.76529 0.33704 0.08845 H 1.90150 2.86860 0.25839 H -2.26152 1.94887 -0.03474 H -0.45178 3.59907 0.14271 N -1.99056 -0.71294 -0.16673 C -2.18013 -1.48907 1.04523 H -1.22527 -1.81229 1.45684 H -2.70325 -0.90340 1.81951 C -3.25673 -0.27339 -0.69586 H -3.87391 -1.14919 -0.91009 H -3.82435 0.36379 0.00391 H -3.10947 0.27885 -1.62472 C 0.74838 -1.53556 -0.26615 H -2.78011 -2.37627 0.82686 C 2.05744 -1.92665 -0.25327 C 3.07857 -0.98301 -0.05690 H 2.31128 -2.96896 -0.40797 H -0.03521 -2.25986 -0.45145 H 4.11388 -1.30318 -0.04076 H 3.54699 1.07939 0.21432 Aromatic amine 9 M06/def2-TZVP Geometry C -0.50842 -0.78682 -0.02619 C -1.83409 -0.38352 -0.01218 C -2.13441 0.97287 -0.00007 C -1.10605 1.89708 0.00589 C 0.21677 1.50009 -0.00404 C 0.54577 0.13756 -0.02618 H -3.16938 1.29751 0.00501 H 0.99315 2.25315 0.00047 H -1.33477 2.95720 0.01683 N 1.85793 -0.27893 -0.05277 C 2.91778 0.68827 0.03142 H 2.88376 1.40245 -0.79912 H 2.88807 1.26530 0.96543 C 2.16895 -1.68035 0.01481 H 3.24891 -1.81136 -0.02036 H 1.80227 -2.14878 0.93804 H 1.74122 -2.23412 -0.82877 H 3.87710 0.17617 -0.01508 H -0.29814 -1.84968 -0.03958 C -2.92868 -1.40239 0.02175 H -3.80598 -1.06160 -0.53133 H -2.60616 -2.35482 -0.40238 H -3.25137 -1.59567 1.04897 Aromatic amine 10 M06/def2-TZVP Geometry C 0.11509 -0.59148 -0.01954 C -1.13562 0.01535 -0.00831 C -1.24328 1.39931 0.00056 C -0.07924 2.15097 0.00017 C 1.16820 1.56552 -0.01166 C 1.29009 0.16588 -0.02732 H -2.20505 1.89345 0.01038 H 2.04738 2.19488 -0.00842 H -0.14985 3.23324 0.01107 N 2.52454 -0.44008 -0.05119 C 3.71777 0.35786 0.03551 H 3.77467 0.93037 0.97076 H 4.58887 -0.29291 -0.01146 C 2.62246 -1.87277 0.01943 H 2.19749 -2.27795 0.94737 H 2.10873 -2.35659 -0.81882 H 3.67005 -2.16447 -0.02457 H 3.79229 1.06965 -0.79405 H 0.16115 -1.67375 -0.02198 S -2.51030 -1.08867 -0.00464 C -3.92269 0.02112 0.02460 H -3.95510 0.65461 -0.86259 H -4.80338 -0.61986 0.03048 H -3.93075 0.63809 0.92392 Aromatic amine 11 M06/def2-TZVP Geometry C -0.28895 -0.60286 -0.00776 C -1.51720 0.02516 -0.00111 C -1.64897 1.40040 0.00361 C -0.48581 2.15089 0.00254 C 0.76060 1.55817 -0.00418 C 0.88774 0.16035 -0.01214 H -2.62795 1.86000 0.00943 H 1.64051 2.18670 -0.00310 H -0.55259 3.23296 0.00802 N 2.11954 -0.44537 -0.02466 C 3.31436 0.35460 0.01249 H 3.37852 0.96541 0.92180 H 4.18451 -0.29828 -0.01212 C 2.21713 -1.88009 0.00813 H 1.77034 -2.30690 0.91491 H 1.72512 -2.34371 -0.85480 H 3.26569 -2.16977 -0.01465 H 3.38144 1.03074 -0.84771 H -0.25897 -1.68327 -0.00940 Cl -2.95158 -0.96212 0.00299 HE M06/def2-TZVP Geometry C 0.00003 0.10426 0.01095 C -1.25800 -0.72479 0.00295 C -1.21880 -2.07311 0.00599 N 0.00006 -2.71383 0.01228 C 1.21891 -2.07308 0.00594 C 1.25808 -0.72477 0.00299 C -2.38939 -2.99666 0.00159 C 2.38951 -2.99663 0.00152 C 2.54834 -0.03742 -0.00601 C -2.54828 -0.03751 -0.00626 O 2.38252 1.30036 0.00315 O -2.38257 1.30028 0.00331 O -3.64439 -0.54625 -0.02065 O 3.64447 -0.54612 -0.01988 C 3.57713 2.07634 -0.00477 C 3.18026 3.52379 0.00595 C -3.57725 2.07613 -0.00477 C -3.18055 3.52362 0.00673 H 0.00001 0.77414 0.87918 H 0.00005 0.78896 -0.84520 H 0.00007 -3.71924 0.01311 H -3.04395 -2.81004 0.85194 H -3.00477 -2.84952 -0.88559 H -2.05856 -4.03710 0.03156 H 3.00558 -2.84860 -0.88502 H 2.05867 -4.03710 0.03017 H 3.04338 -2.81091 0.85262 H 4.16738 1.81979 -0.88957 H 4.18434 1.81153 0.86602 H 2.59525 3.76115 0.89599 H 2.57875 3.76973 -0.87066 H 4.06809 4.15786 0.00073 H -4.18480 1.81088 0.86564 H -4.16710 1.81990 -0.88994 H -2.59605 3.76070 0.89719 H -2.57858 3.76997 -0.86945 H -4.06844 4.15759 0.00128 N-Me pyrrole M06/def2-TZVP Geometry N -0.62070 0.00000 -0.03413 C 0.17340 -1.11101 -0.01253 C 1.48085 -0.70654 0.01382 C 1.48086 0.70654 0.01382 C 0.17341 1.11101 -0.01253 C -2.05788 -0.00000 0.02328 H -0.26405 -2.09772 -0.02197 H 2.34272 -1.35492 0.01986 H 2.34272 1.35492 0.01987 H -0.26404 2.09773 -0.02196 H -2.44653 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-0.70759 C -2.02438 0.36637 0.70732 C -0.85558 -0.21824 1.11227 C 1.20707 -1.06362 0.00040 H -0.45635 -0.40516 -2.09767 H -2.80209 0.73798 -1.35545 H -2.80206 0.73905 1.35490 H -0.45630 -0.40348 2.09798 H 1.34804 -1.70897 0.87470 H 1.34804 -1.70962 -0.87342 C 2.23342 0.02373 -0.00001 C 1.96918 1.31749 -0.00051 H 2.76337 2.05312 -0.00079 H 0.94929 1.69022 -0.00066 H 3.26458 -0.32215 0.00014 N-Bn pyrrole M06/def2-TZVP Geometry N -1.54062 -0.66211 -0.00001 C -2.15296 -0.15499 -1.11225 C -3.17220 0.66336 -0.70719 C -3.17218 0.66331 0.70728 C -2.15294 -0.15506 1.11227 C -0.30918 -1.40476 -0.00005 H -1.80265 -0.42122 -2.09807 H -3.85448 1.19086 -1.35475 H -3.85446 1.19077 1.35489 H -1.80262 -0.42136 2.09807 H -0.30505 -2.06245 0.87560 H -0.30506 -2.06239 -0.87574 C 3.27660 0.95112 0.00001 C 2.04467 1.57956 0.00003 C 0.87611 0.83356 0.00002 C 0.93247 -0.55139 -0.00003 C 2.17366 -1.17674 -0.00005 C 3.33885 -0.43367 -0.00003 H 4.18819 1.53712 0.00002 H 1.98805 2.66201 0.00007 H -0.08723 1.33339 0.00004 H 2.22253 -2.26242 -0.00008 H 4.29967 -0.93545 -0.00005 N-iPr pyrrole M06/def2-TZVP Geometry N -0.12810 -0.10024 -0.15829 C -1.09131 -0.98095 -0.56169 C -2.31666 -0.47484 -0.22004 C -2.08909 0.76045 0.42582 C -0.73455 0.96157 0.45340 C 1.30643 -0.33185 -0.25636 H -0.81785 -1.89520 -1.06645 H -3.27015 -0.93685 -0.42121 H -2.83400 1.43341 0.82043 H -0.15672 1.77632 0.86118 H 1.41328 -1.17493 -0.94754 C 1.88084 -0.72746 1.09005 H 2.94130 -0.97227 1.00012 H 1.78294 0.09533 1.80309 H 1.35684 -1.59338 1.49785 C 2.02019 0.86767 -0.84339 H 1.57746 1.16408 -1.79514 H 1.97445 1.72293 -0.16467 H 3.07411 0.63474 -1.00641 N-tBu pyrrole M06/def2-TZVP Geometry N 0.31949 0.02488 -0.00000 C 1.10851 -1.09503 0.00004 C 2.42127 -0.71055 0.00002 C 2.44060 0.70023 -0.00005 C 1.13876 1.12302 -0.00006 C -1.15337 -0.00070 0.00001 H 0.67677 -2.08337 0.00009 H 3.27189 -1.37387 0.00004 H 3.30874 1.34025 -0.00008 H 0.74183 2.12380 -0.00010 C -1.63549 -0.72178 1.25098 H -2.72774 -0.73402 1.28012 H -1.28662 -1.75552 1.27794 H -1.26990 -0.21604 2.14736 C -1.63550 -0.72190 -1.25089 H -1.26993 -0.21625 -2.14733 H -1.28664 -1.75564 -1.27775 H -2.72775 -0.73414 -1.28001 C -1.70111 1.41430 -0.00006 H -1.38865 1.96750 -0.88830 H -2.79174 1.37011 -0.00005 H -1.38864 1.96759 0.88813 Pyrrole M06/def2-TZVP Geometry N -1.11554 0.00000 -0.00000 C -0.32884 1.11598 -0.00000 C 0.97627 0.70759 -0.00000 C 0.97627 -0.70759 0.00000 C -0.32885 -1.11598 0.00000 H -0.75966 2.10408 -0.00001 H 1.83894 1.35460 -0.00000 H 1.83893 -1.35461 0.00000 H -0.75967 -2.10408 0.00000 H -2.11888 0.00000 0.00000 N-Me 2-butyl pyrrole M06/def2-TZVP Geometry N 1.94693 0.52061 0.00000 C 2.95762 -0.40385 -0.00000 C 2.39978 -1.65005 -0.00001 C 0.99601 -1.47759 -0.00001 C 0.73793 -0.12955 -0.00000 H 3.98894 -0.08604 -0.00000 H 2.93831 -2.58431 -0.00002 H 0.25170 -2.25882 -0.00001 C 2.12603 1.94641 0.00001 H 1.67869 2.40549 -0.88567 H 1.67869 2.40548 0.88570 H 3.19178 2.16996 0.00002 C -0.54236 0.62389 0.00000 H -0.58575 1.29201 0.87274 H -0.58575 1.29201 -0.87272 C -1.77216 -0.26054 -0.00000 H -1.74850 -0.92104 -0.87538 H -1.74850 -0.92104 0.87537 C -3.06364 0.53240 0.00000 H -3.08121 1.19395 0.87455 H -3.08121 1.19396 -0.87454 C -4.28982 -0.35507 -0.00000 H -5.21472 0.22406 0.00000 H -4.30365 -1.00309 -0.88053 H -4.30365 -1.00310 0.88051 N-Me 3-Pr pyrrole M06/def2-TZVP Geometry N -1.86763 -0.14075 0.01662 C -1.58729 1.05332 -0.58014 C -0.28745 1.38039 -0.30242 C 0.25459 0.34191 0.49693 C -0.74520 -0.57977 0.66498 H -2.34423 1.57367 -1.14721 H 0.22215 2.27793 -0.62045 C -3.09935 -0.87134 -0.10423 H -3.05822 -1.60892 -0.91075 H -3.31775 -1.39126 0.82961 H -3.91604 -0.17914 -0.30963 H -0.74715 -1.51607 1.20438 C 1.64459 0.25702 1.02655 H 1.85372 1.12236 1.66549 H 1.72921 -0.62694 1.67024 C 2.70453 0.17916 -0.06700 H 2.63720 1.07506 -0.69474 H 3.69630 0.20646 0.39614 C 2.56998 -1.05922 -0.92745 H 3.36393 -1.12212 -1.67386 H 2.61520 -1.96506 -0.31495 H 1.61270 -1.06944 -1.45395 N-Me dihydroindole M06/def2-TZVP Geometry N -1.61912 -0.20190 0.02344 C -1.98550 1.11710 -0.01418 C -0.85240 1.88191 -0.06039 C 0.25233 0.99576 -0.05072 C -0.25161 -0.27850 -0.00355 H -3.02847 1.39448 -0.00228 H -0.81849 2.96047 -0.08975 C -2.51522 -1.32357 0.06560 H -3.53757 -0.96013 0.16025 H -2.44762 -1.92686 -0.84430 H -2.29933 -1.96912 0.92087 C 1.71842 1.26730 -0.06910 H 2.04371 1.54965 -1.07941 H 1.96393 2.11887 0.57315 C 2.48500 0.02830 0.37770 H 3.55555 0.16060 0.19993 H 2.35911 -0.10472 1.45957 C 1.98460 -1.22034 -0.33386 H 2.62230 -2.07728 -0.10255 H 2.05108 -1.06034 -1.41687 C 0.53794 -1.53441 0.03390 H 0.50033 -1.98720 1.03560 H 0.12802 -2.28635 -0.65067 OH imine M06/def2-TZVP Geometry N 2.28360 -0.47405 -0.00000 C 1.43326 0.46803 -0.00000 C 0.00000 0.20872 0.00000 O 3.57447 0.00788 -0.00000 C -0.52136 -1.08494 0.00000 C -1.88607 -1.28413 0.00000 C -2.75418 -0.20065 0.00000 C -2.24680 1.08605 0.00000 C -0.87782 1.28800 0.00000 H 1.76794 1.50904 -0.00000 H 4.11001 -0.79087 -0.00000 H 0.16138 -1.92623 -0.00000 H -2.28200 -2.29313 0.00000 H -3.82565 -0.36306 0.00000 H -2.91828 1.93661 0.00000 H -0.47645 2.29653 0.00000 H2O2 M06/def2-TZVP Geometry O 0.00000 0.71060 -0.05745 H -0.79283 0.89892 0.45962 O -0.00000 -0.71060 -0.05745 H 0.79283 -0.89892 0.45962 Carbonyl 15 M06/def2-TZVP Geometry C -0.30471 -0.82361 0.40585 C 0.72902 0.04273 -0.29014 C -1.73486 -0.43176 0.20325 O -2.12264 0.42724 -0.53475 C 2.08232 -0.64302 -0.27115 H -0.11627 -0.86358 1.48879 H -0.23152 -1.87085 0.07776 H 0.40849 0.17247 -1.33053 C 0.81637 1.41318 0.35772 H -2.45925 -1.03754 0.79904 H 2.05275 -1.61529 -0.76926 H 2.41479 -0.80710 0.75962 H 2.84088 -0.03363 -0.76729 H 1.55230 2.03980 -0.15085 H -0.14149 1.93414 0.33468 H 1.13151 1.31848 1.40289 Carbonyl 16 M06/def2-TZVP Geometry C 0.41069 1.03128 0.00007 C -0.70050 -0.01581 0.00009 C 1.83998 0.58466 -0.00022 O 2.24517 -0.54180 -0.00030 C -0.62125 -0.88309 -1.24999 H 0.30333 1.70015 0.86748 H 0.30308 1.70038 -0.86713 C -0.62130 -0.88307 1.25019 C -2.03043 0.72784 0.00006 H 2.55870 1.44055 0.00006 H 0.30361 -1.45970 -1.28075 H -0.67546 -0.26922 -2.15463 H -1.46053 -1.58371 -1.27551 H -2.86444 0.02090 0.00004 H -2.13009 1.36334 0.88519 H -2.13005 1.36335 -0.88507 H -1.46062 -1.58364 1.27572 H 0.30353 -1.45973 1.28097 H -0.67548 -0.26918 2.15481 Carbonyl 64 M06/def2-TZVP Geometry C -0.11006 -1.01537 0.97068 C -0.67187 0.38574 0.78754 C 0.42653 1.41241 0.52119 C 1.30868 0.99060 -0.64160 C 1.89915 -0.38835 -0.40158 C 0.80399 -1.41696 -0.17664 C -1.73411 0.46572 -0.27631 O -2.27622 -0.46230 -0.80132 H 0.45769 -1.03800 1.90861 H -0.92911 -1.73096 1.07319 H -1.20234 0.69244 1.70286 H -0.01827 2.39625 0.33562 H 1.03924 1.51303 1.42416 H 0.71340 0.97227 -1.56518 H 2.09915 1.72890 -0.80072 H 2.53415 -0.68380 -1.24109 H 2.54975 -0.34857 0.48266 H 1.23815 -2.40009 0.02362 H 0.21077 -1.52232 -1.09174 H -2.01666 1.51651 -0.54101 Carbonyl 65 M06/def2-TZVP Geometry C 1.10665 -1.25156 0.04386 C 0.34011 -0.00006 -0.35429 C 1.10519 1.25234 0.04384 C -0.98806 -0.00088 0.34687 O -2.06123 -0.00031 -0.17819 H 2.09710 -1.25563 -0.41550 H 1.24677 -1.28671 1.12912 H 0.14169 -0.00019 -1.43037 H 1.24525 1.28768 1.12910 H -0.89152 0.00055 1.46531 H 0.58707 -2.16233 -0.25915 H 0.58454 2.16250 -0.25919 H 2.09564 1.25758 -0.41550 Carbonyl 66 M06/def2-TZVP Geometry C 1.54750 1.24040 0.00054 O 1.73107 2.42707 -0.00060 H 2.39622 0.52725 -0.00069 C -2.37555 -0.42333 -0.00019 C -1.28929 -1.27793 -0.00016 C -0.00914 -0.75273 0.00006 C 0.20321 0.62360 0.00026 C -0.90973 1.46176 0.00022 C -2.18917 0.95127 0.00000 H -3.37695 -0.83788 -0.00036 H -1.42281 -2.35247 -0.00031 Cl 1.32096 -1.87291 0.00008 H -0.72528 2.53034 0.00038 H -3.04318 1.61742 -0.00002 Carbonyl 67 M06/def2-TZVP Geometry C -3.16536 0.33114 -0.00000 O -3.92187 -0.59730 0.00001 H -3.53400 1.38314 0.00001 C 1.03544 0.01039 -0.00002 C 0.46596 1.26806 -0.00002 C -0.91251 1.35926 -0.00001 C -1.69145 0.21020 -0.00001 C -1.09123 -1.04488 -0.00001 C 0.28269 -1.15148 -0.00002 H 1.10182 2.14267 -0.00002 H -1.39561 2.33114 -0.00001 H -1.72350 -1.92500 -0.00001 H 0.78414 -2.10967 -0.00002 N 2.51085 -0.09927 -0.00003 O 2.98427 -1.21115 0.00004 O 3.14384 0.93051 0.00005 Carbonyl 69 M06/def2-TZVP Geometry C -3.56875 0.30545 0.00000 O -4.32231 -0.62798 0.00000 H -3.94747 1.35499 -0.00001 C 0.64952 0.03599 -0.00000 C 0.05010 1.28343 -0.00001 C -1.33000 1.35770 -0.00001 C -2.10011 0.20301 0.00000 C -1.47809 -1.04170 0.00001 C -0.10282 -1.13078 0.00001 H 0.65896 2.17865 -0.00002 H -1.82193 2.32585 -0.00002 H -2.09646 -1.93229 0.00002 H 0.39410 -2.09297 0.00002 Br 2.53349 -0.08254 -0.00000 Carbonyl 70 M06/def2-TZVP Geometry C -2.77911 0.32910 0.00001 O -3.54164 -0.59500 0.00000 H -3.14211 1.38335 0.00005 C 1.44778 -0.01420 -0.00000 C 0.85510 1.24537 0.00002 C -0.52127 1.34524 0.00002 C -1.30745 0.20144 0.00001 C -0.71160 -1.05577 -0.00001 C 0.66019 -1.16697 -0.00002 H 1.47984 2.12978 0.00003 H -0.99903 2.31991 0.00003 H -1.34805 -1.93303 -0.00002 H 1.14036 -2.13774 -0.00003 N 4.01690 -0.22003 -0.00001 C 2.87034 -0.12790 -0.00001 Carbonyl 71 M06/def2-TZVP Geometry C 2.02630 -0.51987 0.00009 O 2.92921 0.27243 -0.00007 H 2.21901 -1.61847 0.00001 S -1.92923 -0.37494 0.00019 C -0.39095 -1.09880 -0.00006 C 0.60861 -0.16459 0.00001 C 0.10762 1.16436 -0.00009 C -1.24570 1.20395 -0.00026 H -0.28026 -2.17380 -0.00005 H 0.75200 2.03316 -0.00014 H -1.89208 2.06841 -0.00042 Carbonyl 72 M06/def2-TZVP Geometry C 1.72281 0.44733 -0.00002 O 2.57832 -0.39652 -0.00002 H 1.97937 1.53238 -0.00002 O -1.89639 0.51780 0.00000 C -0.69556 1.10509 0.00003 C 0.29507 0.17372 -0.00000 C -0.36129 -1.09613 0.00002 C -1.67927 -0.82719 -0.00001 H -0.67933 2.18400 0.00004 H 0.11767 -2.06138 0.00002 H -2.56365 -1.44218 -0.00002 Carbonyl 73 M06/def2-TZVP Geometry C 1.94333 -0.15149 0.04984 O 1.65356 -1.28063 -0.19965 C 1.02800 1.02507 -0.13809 O -0.21528 0.65684 -0.67272 C -1.07402 0.08372 0.20262 C -2.27750 -0.42993 -0.51032 O -0.86185 0.01690 1.37676 H 2.94664 0.13056 0.44626 H 1.49284 1.72466 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0.30197 1.86876 H -1.24986 1.55666 1.13179 H -0.04630 2.17549 0.00594 H -0.71747 0.47994 -1.67587 H -2.24764 1.13510 -1.08808 H -2.45782 -0.69084 0.53368 H -1.95319 -1.52059 -0.93287 H 0.29230 -1.76847 -0.13727 H -0.51471 -1.74022 1.42326 Carbonyl 76 M06/def2-TZVP Geometry C -1.21754 -1.03618 -0.14192 O -2.31830 -0.59898 -0.01073 C 0.03775 -0.37575 0.41845 O -0.09567 0.96705 0.70301 O 1.05645 -0.67629 -0.47783 C 2.33853 -0.36575 0.00846 C -0.35293 1.79471 -0.41224 H -1.00799 -1.99938 -0.66102 H 0.23856 -0.85317 1.39693 H 3.06143 -0.71520 -0.72722 H 2.46757 0.71122 0.15631 H 2.52652 -0.87100 0.96473 H -1.30218 1.54355 -0.89326 H -0.40989 2.81473 -0.03618 H 0.45133 1.73278 -1.15238 Carbonyl 77 M06/def2-TZVP Geometry O -0.00001 1.83834 -0.00000 C -0.00000 0.64659 0.00000 C -1.21558 -0.19373 -0.38528 C 1.21558 -0.19372 0.38530 O 2.33606 0.28836 -0.11189 O -2.33606 0.28836 0.11189 O -1.09799 -1.13372 -1.11757 O 1.09800 -1.13370 1.11758 C 3.53924 -0.40333 0.26314 C 4.68322 0.26286 -0.43895 C -3.53924 -0.40334 -0.26315 C -4.68322 0.26287 0.43893 H 3.63657 -0.36102 1.35123 H 3.43510 -1.45605 -0.01282 H 4.56044 0.21007 -1.52148 H 4.75736 1.31302 -0.15381 H 5.61939 -0.23116 -0.17610 H -3.63655 -0.36103 -1.35123 H -3.43511 -1.45605 0.01283 H -4.75735 1.31302 0.15377 H -5.61939 -0.23115 0.17606 H -4.56046 0.21009 1.52145 Carbonyl 78 M06/def2-TZVP Geometry O -0.45341 1.81723 -0.00019 C -0.56921 0.63618 0.00003 C -1.96891 -0.03200 -0.00000 C 0.61888 -0.33975 0.00004 O 1.75664 0.32315 0.00010 O 0.48196 -1.52760 -0.00012 C 2.94935 -0.48026 0.00004 C 4.12360 0.45012 0.00011 F -2.12102 -0.78512 -1.07968 F -2.12094 -0.78532 1.07956 F -2.90744 0.89215 0.00012 H 2.92923 -1.12885 0.87999 H 2.92923 -1.12871 -0.88001 H 5.05098 -0.12374 0.00007 H 4.11572 1.08902 -0.88372 H 4.11572 1.08889 0.88404 Carbonyl 79 M06/def2-TZVP Geometry C 0.88878 0.70699 0.07198 C -0.30230 1.61586 0.16319 O -1.47487 0.95678 0.57935 C 1.29616 -0.01266 1.18975 C 2.38503 -0.86080 1.11962 C 3.08366 -0.99756 -0.07073 C 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1.07952 -0.90936 C -3.72092 1.65999 0.15049 C -2.44436 1.23331 0.47235 C 2.50969 0.67012 0.28109 C 3.46705 1.66947 0.27069 C 3.08386 2.99623 0.16130 C 1.74238 3.31606 0.04943 C 0.78779 2.31203 0.05514 H 2.62316 -1.50658 -3.45074 H 0.79447 -0.16422 -2.47146 H 0.23985 -1.74010 -3.00178 H -1.59603 -0.12946 2.82104 H -0.55746 -1.07493 3.88709 H 0.09394 0.34813 3.06743 H 1.59359 -2.60741 1.26483 H 1.95457 -1.22866 2.31572 H 1.14931 -2.65022 2.97932 H -0.88692 -3.22404 0.83031 H -1.22288 -3.12165 2.56335 H -2.17367 -2.16241 1.42297 H -2.06334 -1.15878 -1.87908 H -4.32334 -0.39385 -2.46389 H -5.39783 1.41281 -1.16390 H -4.19042 2.44731 0.72930 H -1.93332 1.69951 1.31062 H 2.83067 -0.36502 0.34660 H 4.51710 1.41077 0.34600 H 3.83277 3.78007 0.15535 H 1.43671 4.35157 -0.04916 H -0.25722 2.58279 -0.05541 Carbonyl 113 M06/def2-TZVP Geometry C -3.40009 -0.10068 0.71329 C -2.22937 -0.48239 -0.15720 O -4.53617 -0.13918 0.34890 O -1.04686 -0.41993 0.56928 Si 0.43724 0.04565 -0.01369 C 0.23991 1.73579 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6.22409 0.33116 H 1.59102 4.05204 0.22351 H -2.06983 2.13308 -0.85966 H -3.23951 4.28954 -0.74362 Silanyloxy oxazole 4 M06/def2-TZVP Geometry N 1.86133 -1.67187 -1.09122 C 0.55181 -1.35625 -1.39431 C 0.36954 -0.03817 -1.14509 O 1.54499 0.48436 -0.70673 C 2.40260 -0.56954 -0.69129 C 3.75840 -0.33429 -0.23688 C -0.45616 -2.35410 -1.84349 O -0.66387 0.76542 -1.24915 Si -1.42707 1.53152 0.05755 C -0.32896 2.95025 0.62734 C -3.07246 2.05868 -0.67653 C 4.67625 -1.38266 -0.25382 C 5.96974 -1.17950 0.18236 C 6.36602 0.06815 0.64025 C 5.45761 1.11315 0.65930 C 4.16011 0.91722 0.22416 C -1.09277 3.87046 1.57409 C 0.32696 3.74133 -0.49653 C -3.81814 0.84765 -1.22819 C -2.93705 3.12772 -1.75363 C -1.65735 0.23641 1.40852 C -2.84201 0.52041 2.32554 C -0.40164 -0.00935 2.23710 C -1.38761 -2.78265 -0.73976 C -2.76264 -2.65469 -0.87246 C -3.61365 -3.00406 0.16527 C -3.09564 -3.49352 1.35106 C -1.72279 -3.63788 1.48960 C -0.87788 -3.28429 0.45390 H -1.04581 -1.94183 -2.66846 H 0.08416 -3.21999 -2.23800 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-0.28514 C -2.44868 -1.34720 -0.35764 C 0.65142 -2.74630 -1.35142 O 0.44216 0.35677 -0.63565 Si 0.45464 1.85628 0.16141 C -0.03496 1.63381 1.97592 C 2.26022 2.34878 0.03175 C 0.18507 0.21174 2.48787 C -1.44105 2.10267 2.32925 C 2.74701 2.44523 -1.40897 C 3.14949 1.39116 0.81709 C -0.71661 3.01579 -0.74418 C -0.78512 2.79107 -2.24867 C -0.37179 4.46639 -0.42022 C 1.93391 -2.51377 -0.60017 C 1.97815 -2.66994 0.78101 C 3.15895 -2.48689 1.47747 C 4.31996 -2.14332 0.80171 C 4.28648 -1.97852 -0.57150 C 3.09974 -2.16057 -1.26433 H 0.32870 -3.78416 -1.22217 H 0.83511 -2.61795 -2.42380 H 0.67673 2.28946 2.50193 H 2.32705 3.34462 0.49430 H 0.06861 0.17460 3.57513 H -0.55796 -0.47544 2.06831 H 1.17252 -0.18685 2.24254 H -1.61353 2.01167 3.40614 H -1.61978 3.14540 2.05741 H -2.20097 1.49490 1.83059 H 3.81238 2.69442 -1.44084 H 2.62256 1.48813 -1.92564 H 2.21547 3.20686 -1.98385 H 4.19990 1.69038 0.74266 H 2.89563 1.35021 1.87916 H 3.07526 0.37510 0.41723 H -1.71067 2.80260 -0.33033 H -1.10188 1.77677 -2.49966 H 0.18194 2.95956 -2.72976 H -1.49890 3.48210 -2.70816 H -0.29466 4.65166 0.65617 H 0.58407 4.75373 -0.86895 H -1.13067 5.14808 -0.81554 H 1.07008 -2.94096 1.31246 H 3.17561 -2.61763 2.55367 H 5.24607 -2.00140 1.34624 H 5.18737 -1.70462 -1.10852 H 3.07690 -2.02999 -2.34192 C -3.88748 -1.26771 0.02544 F -4.54892 -0.40760 -0.74938 F -4.46443 -2.44722 -0.06980 F -4.01953 -0.83142 1.28127 Silanyloxy oxazole 6 M06/def2-TZVP Geometry C -2.15880 -1.10570 -0.36478 N -2.06728 -2.38227 -0.50698 C -0.72340 -2.64073 -0.66964 C -0.04897 -1.46837 -0.61781 O -0.95046 -0.47255 -0.43032 O 1.21543 -1.14734 -0.71576 C -3.33684 -0.29130 -0.14513 C -3.24323 1.08533 0.04461 C -4.38445 1.83723 0.25462 C -5.62745 1.22781 0.27855 C -5.72469 -0.14308 0.09172 C -4.59014 -0.89995 -0.11879 Si 2.07251 0.15473 -0.05932 C 2.02499 1.55400 -1.32314 C 3.17667 2.54277 -1.17402 C 0.69540 2.29676 -1.35662 C 1.28404 0.64121 1.58036 C 2.18140 1.61498 2.33842 C 0.88681 -0.52762 2.47458 C 3.81545 -0.53465 0.07289 C 4.31377 -0.98880 -1.29634 C 3.93096 -1.67676 1.07468 H -0.32703 -3.63251 -0.80876 H -2.27041 1.56425 0.02948 H -4.30199 2.90787 0.40126 H -6.52030 1.81945 0.44294 H -6.69537 -0.62480 0.10997 H -4.65123 -1.97164 -0.26659 H 2.14693 1.03574 -2.28543 H 3.14195 3.29519 -1.96811 H 3.12033 3.08387 -0.22456 H 4.15718 2.06389 -1.22009 H 0.68744 3.03984 -2.16010 H -0.15374 1.62843 -1.51244 H 0.52383 2.83826 -0.41991 H 0.36434 1.17464 1.30370 H 1.70277 1.94131 3.26698 H 3.13244 1.14902 2.61571 H 2.41228 2.51243 1.75842 H 0.35049 -0.16563 3.35732 H 0.23663 -1.24802 1.97168 H 1.76188 -1.07400 2.83431 H 4.44991 0.29458 0.41648 H 5.34239 -1.35651 -1.23085 H 3.69934 -1.80878 -1.67876 H 4.29777 -0.19032 -2.04210 H 4.93293 -2.11666 1.04590 H 3.74645 -1.35303 2.10084 H 3.21965 -2.47676 0.84580 Nitrostyrene 1 M06/def2-TZVP Geometry C -0.60922 0.44132 0.00003 C -1.58865 -0.45464 -0.00018 C 0.81606 0.17450 0.00005 C 1.69580 1.25638 -0.00009 C 3.06380 1.05927 -0.00012 C 3.57452 -0.22658 0.00002 C 2.71175 -1.31385 0.00018 C 1.34741 -1.11718 0.00020 H -0.91523 1.48461 0.00020 H -1.49996 -1.53103 -0.00039 H 1.29077 2.26288 -0.00018 H 3.73271 1.91147 -0.00023 H 4.64634 -0.38579 0.00000 H 3.11041 -2.32132 0.00030 H 0.68539 -1.97554 0.00035 N -2.97772 -0.02973 -0.00011 O -3.23508 1.15433 0.00021 O -3.79933 -0.92339 -0.00019 Nitrostyrene 2 M06/def2-TZVP Geometry C -2.29405 0.46416 0.00002 C -3.22232 -0.48455 -0.00024 C -0.85713 0.27789 0.00006 C -0.03815 1.40613 -0.00009 C 1.33825 1.29453 -0.00011 C 1.90998 0.03536 0.00006 C 1.12095 -1.10590 0.00024 C -0.25065 -0.98032 0.00024 H -2.65752 1.48875 0.00020 H -3.07518 -1.55464 -0.00048 H -0.49505 2.39001 -0.00021 H 1.96559 2.17693 -0.00023 Br 3.78796 -0.13567 0.00006 H 1.58558 -2.08401 0.00040 H -0.85882 -1.87756 0.00042 N -4.63287 -0.13453 -0.00019 O -4.95186 1.03421 0.00011 O -5.40494 -1.07083 -0.00034 Nitrostyrene 3 M06/def2-TZVP Geometry C -1.53547 -0.44177 -0.00000 C -2.53141 0.43999 -0.00000 C -0.11989 -0.15857 -0.00000 C 0.78102 -1.21928 0.00002 C 2.14883 -1.01753 0.00002 C 2.64531 0.28035 0.00001 C 1.75651 1.35920 -0.00001 C 0.40431 1.14146 -0.00002 H -1.82787 -1.48906 -0.00000 H -2.45773 1.51743 -0.00000 H 0.39569 -2.23364 0.00003 H 2.81418 -1.87033 0.00004 O 3.94911 0.59798 0.00001 H 2.16773 2.36141 -0.00003 H -0.26486 1.99432 -0.00003 N -3.90940 -0.00525 -0.00001 O -4.15074 -1.19416 -0.00002 O -4.74774 0.87439 -0.00002 C 4.89403 -0.44289 0.00003 H 5.87480 0.02799 0.00003 H 4.79974 -1.07138 0.89179 H 4.79975 -1.07140 -0.89172 Nitrostyrene 4 M06/def2-TZVP Geometry C -0.28318 0.52469 0.00002 C -1.22591 -0.41496 0.00002 H -0.60184 1.56228 0.00002 H -1.07160 -1.48352 0.00001 N -2.62480 -0.04420 -0.00006 O -2.92376 1.13184 -0.00005 O -3.41581 -0.96537 -0.00007 C 1.11793 0.28791 0.00003 C 2.17608 1.14912 0.00011 C 3.34464 0.35327 -0.00016 C 2.91520 -0.93219 0.00012 O 1.57299 -0.99276 0.00006 H 2.10883 2.22552 0.00014 H 4.36931 0.68611 -0.00033 H 3.43302 -1.87762 0.00016 Nitrostyrene 5 M06/def2-TZVP Geometry C 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C 0.06299 -0.85792 -1.11785 P 1.29685 -0.22503 0.01596 P -1.67423 -0.64504 -0.71527 O 1.36943 -0.94998 1.28659 O 2.60063 -0.24432 -0.87551 O 1.00781 1.32259 0.16899 C 0.41891 1.86731 1.35543 C 3.84272 0.13468 -0.27236 C 4.93829 -0.07792 -1.27443 C 1.48873 2.30551 2.31522 O -2.57213 -1.52444 -1.45855 O -1.75780 -0.75992 0.86427 O -1.86365 0.90989 -0.90845 C -1.68506 -2.05488 1.47986 C -1.45571 -1.85735 2.94790 C -3.11770 1.51965 -0.58601 C -3.13754 2.89464 -1.18547 H -0.41363 -2.00427 -2.80751 H 1.39952 -1.74588 -2.49060 H -0.19204 2.70869 1.01930 H -0.24839 1.12904 1.81021 H 3.77804 1.18613 0.03123 H 3.99701 -0.46635 0.62958 H 5.89997 0.20981 -0.84709 H 4.99414 -1.12705 -1.56855 H 4.76603 0.52134 -2.16964 H 2.16127 3.02391 1.84165 H 2.07258 1.44546 2.64952 H 1.04381 2.78028 3.19180 H -0.85713 -2.61831 1.03473 H -2.61533 -2.58943 1.26724 H -1.43129 -2.82145 3.45819 H -0.49947 -1.35682 3.10854 H -2.25471 -1.25685 3.38707 H -3.93086 0.89887 -0.97669 H -3.21435 1.55581 0.50485 H -4.07261 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-0.02170 N 1.90751 0.63275 0.21078 C 0.85041 1.29051 -0.32402 C 0.03424 0.25122 -1.10373 C 1.34850 -1.53902 1.22556 C 3.20390 -1.35872 -0.45223 C 2.82375 1.26266 1.12717 O 0.60374 2.47122 -0.21015 H 1.38473 -0.98085 -1.99226 H -0.09980 0.62940 -2.11909 H 0.36873 -1.15876 1.51428 H 1.26090 -2.60526 1.01724 H 2.03909 -1.40362 2.05937 H 3.91852 -1.32590 0.37030 H 3.09312 -2.39822 -0.76276 H 3.60207 -0.77573 -1.28458 H 3.85593 1.13671 0.79627 H 2.58261 2.32364 1.15194 H 2.72208 0.85317 2.13496 C -3.89686 -0.33578 0.56698 C -3.42394 0.94568 0.31552 C -2.15551 1.13321 -0.21272 C -1.34239 0.03606 -0.49173 C -1.82091 -1.24501 -0.24430 C -3.09221 -1.42928 0.28442 H -4.88730 -0.47985 0.97899 H -4.04547 1.80509 0.53205 H -1.78231 2.13182 -0.40006 H -1.18772 -2.09288 -0.46889 H -3.45365 -2.43215 0.47353 Amine 17 M06-2X/def2-TZVP Geometry N -1.73994 -0.65534 -1.19456 C -2.39211 0.61673 -0.86866 N -2.18216 0.74918 0.58258 C -1.84634 -0.42447 1.16371 C -1.68870 -1.44245 0.03656 C -1.73499 1.75897 -1.62368 C -3.88358 0.53193 -1.18256 C -2.53442 1.92102 1.34159 O -1.70993 -0.63711 2.35165 H -0.78544 -0.45134 -1.47519 H -2.55171 -2.11461 0.09243 H -1.78166 1.55726 -2.69421 H -2.24724 2.70254 -1.43294 H -0.68979 1.85715 -1.32330 H -4.02298 0.41541 -2.25666 H -4.32387 -0.33028 -0.68036 H -4.40826 1.43153 -0.85729 H -1.91489 2.77283 1.05603 H -3.58509 2.18565 1.20019 H -2.36659 1.69229 2.39251 C -0.41774 -2.28114 0.18779 H -0.43737 -3.08051 -0.55475 H -0.45982 -2.74081 1.17663 C 3.14698 0.10173 -0.27815 C 2.46697 0.09212 0.93557 C 1.32752 -0.69168 1.08137 C 0.84604 -1.47416 0.03817 C 1.54642 -1.45322 -1.16960 C 2.67945 -0.67863 -1.33367 O 4.26680 0.82844 -0.52371 H 2.81255 0.68093 1.77284 H 0.80096 -0.69263 2.02858 H 1.19745 -2.06252 -1.99649 H 3.22543 -0.66626 -2.26762 C 4.77843 1.61816 0.52506 H 5.05581 1.00293 1.38530 H 4.05440 2.37398 0.84178 H 5.66435 2.10949 0.13192 Amine 18 M06-2X/def2-TZVP Geometry N -1.60842 -1.63530 -0.20551 C -2.11651 -0.57452 -1.09020 N -2.23601 0.58855 -0.20538 C -2.05897 0.29133 1.09696 C -1.65896 -1.17293 1.17864 C -2.58165 1.90918 -0.66330 C -1.13216 -0.30051 -2.21897 C -3.48793 -0.96301 -1.63701 O -2.17798 1.04860 2.04064 C -0.33035 -1.33651 1.94471 C 0.87489 -0.96478 1.13927 C 1.76623 -1.85155 0.60384 N 2.70948 -1.20329 -0.15602 C 2.43470 0.13876 -0.12630 C 1.29116 0.33601 0.68078 C 3.10333 1.19075 -0.75324 C 2.60513 2.46237 -0.55791 C 1.47750 2.68509 0.25000 C 0.82033 1.64287 0.87241 C 3.81984 -1.80613 -0.84932 H -0.64153 -1.81745 -0.44833 H -2.43916 -1.69058 1.74487 H -2.70615 2.53742 0.21690 H -1.78663 2.32316 -1.28752 H -3.51474 1.90033 -1.23008 H -0.18628 0.06568 -1.81204 H -0.95451 -1.22280 -2.77453 H -1.52807 0.43943 -2.91557 H -4.16163 -1.19118 -0.81068 H -3.92155 -0.16309 -2.23962 H -3.38970 -1.85265 -2.25855 H -0.41149 -0.72636 2.84729 H -0.23442 -2.37698 2.26021 H 1.80434 -2.92525 0.71296 H 3.97828 1.01753 -1.36691 H 3.09600 3.30428 -1.02852 H 1.12392 3.69781 0.39344 H -0.03874 1.83255 1.50379 H 3.77210 -1.58804 -1.91784 H 3.77956 -2.88408 -0.71080 H 4.76946 -1.43672 -0.45738 Amine 19 M06-2X/def2-TZVP Geometry C 0.88593 3.06561 2.71160 N 1.12003 2.16842 1.58391 C 0.01290 1.22198 1.58516 C -1.20140 2.10971 1.90186 C -0.62099 3.33852 2.63391 C -0.11318 0.48292 0.23821 C 1.08842 -0.41202 -0.07616 C -1.35987 -0.40184 0.30052 O -0.28766 1.40600 -0.80248 Si 0.62220 2.61892 -1.48090 C 0.21495 4.28798 -0.74583 C 2.46526 2.31558 -1.47440 C 0.03100 2.61094 -3.25633 C -1.38760 -1.50200 1.19608 C -2.49694 -2.28721 1.30732 C -3.64967 -2.03113 0.52427 C -3.62337 -0.94177 -0.38079 C -2.45732 -0.14035 -0.46951 C -4.81598 -2.82769 0.61127 C -5.90718 -2.55330 -0.16445 C -5.88274 -1.46732 -1.06687 C -4.76863 -0.68276 -1.17193 C 2.03524 -0.78182 0.83732 C 3.11523 -1.63297 0.48324 C 3.20499 -2.11769 -0.84368 C 2.19935 -1.74194 -1.77082 C 1.17786 -0.92190 -1.39926 C 4.10703 -2.01054 1.41889 C 5.13899 -2.82849 1.05101 C 5.22871 -3.30973 -0.27259 C 4.28293 -2.96212 -1.19670 H 1.13248 2.59145 3.67180 H 1.48954 3.96946 2.61743 H 2.02425 1.71549 1.62536 H 0.11427 0.46977 2.38123 H -1.68495 2.40665 0.97184 H -1.93518 1.56850 2.49645 H -1.05110 3.47731 3.62427 H -0.81168 4.24508 2.06154 H 0.50383 5.08094 -1.44008 H -0.85961 4.37919 -0.56953 H 0.73451 4.44619 0.19838 H 2.94211 3.10219 -2.06599 H 2.72062 1.35665 -1.92807 H 2.88825 2.34728 -0.47175 H -1.04845 2.76766 -3.30822 H 0.51278 3.40085 -3.83636 H 0.25439 1.65637 -3.73725 H -0.50668 -1.73050 1.78418 H -2.50677 -3.12692 1.99214 H -2.43913 0.69281 -1.15992 H -4.82795 -3.66033 1.30471 H -6.79518 -3.16760 -0.09097 H -6.75266 -1.25974 -1.67645 H -4.74473 0.15109 -1.86339 H 1.98492 -0.44275 1.86606 H 2.25562 -2.12316 -2.78366 H 0.41080 -0.64059 -2.11048 H 4.03505 -1.63979 2.43476 H 5.89235 -3.11103 1.77482 H 6.05004 -3.95668 -0.55183 H 4.34507 -3.32956 -2.21411 Amine 20 M06-2X/def2-TZVP Geometry C -1.30987 -2.28518 2.96364 N -1.38671 -1.33148 1.86105 C -0.01415 -0.93537 1.57602 C 0.75771 -2.26021 1.67688 C -0.10504 -3.15797 2.58952 C 0.11432 -0.25795 0.19720 C -0.67025 1.05550 0.10094 C 1.59830 0.03907 -0.04016 O -0.31929 -1.13598 -0.80829 Si -1.75385 -1.85720 -1.22307 C -3.27604 -0.82517 -0.89303 C -1.57683 -2.06581 -3.07488 C -1.92882 -3.56126 -0.47426 C 2.32016 -0.65833 -0.99255 C 3.68348 -0.41658 -1.17744 C 4.30750 0.53432 -0.38685 C 3.60021 1.25465 0.57739 C 2.24786 0.99951 0.73714 C -1.12089 1.76545 1.20246 C -1.81460 2.97034 1.05379 C -2.04152 3.45411 -0.22305 C -1.58309 2.76948 -1.35092 C -0.89776 1.58047 -1.17218 C -2.29815 3.71331 2.26935 C -1.85203 3.31234 -2.72734 C 4.44519 -1.18365 -2.22372 C 4.30245 2.29038 1.41233 H -1.12692 -1.78655 3.92577 H -2.23786 -2.85247 3.04964 H -1.98364 -0.54063 2.06919 H 0.38115 -0.24337 2.33361 H 0.85645 -2.69847 0.68441 H 1.76090 -2.09714 2.06651 H 0.43209 -3.49286 3.47531 H -0.43372 -4.04417 2.04880 H -3.26482 0.09932 -1.47230 H -4.15626 -1.40091 -1.19255 H -3.38391 -0.56702 0.15937 H -1.46884 -1.09742 -3.56792 H -0.69644 -2.66475 -3.31711 H -2.44976 -2.56513 -3.50079 H -2.26859 -3.51165 0.55943 H -2.65028 -4.14584 -1.05070 H -0.97567 -4.09495 -0.50096 H 1.81467 -1.39733 -1.60061 H 5.36642 0.73002 -0.52266 H 1.68452 1.57208 1.46614 H -0.93468 1.40431 2.20813 H -2.58036 4.38727 -0.35131 H -0.52916 1.03484 -2.03367 H -2.79912 4.63949 1.99184 H -3.00158 3.10767 2.84376 H -1.46653 3.96232 2.93093 H -1.59514 4.37064 -2.78893 H -1.27800 2.77560 -3.48122 H -2.91068 3.21808 -2.97905 H 5.49752 -0.90281 -2.23290 H 4.38064 -2.25792 -2.04283 H 4.03447 -0.99663 -3.21751 H 5.11093 1.84122 1.99204 H 4.74458 3.06414 0.78230 H 3.61405 2.77117 2.10599 Amine 21 M06-2X/def2-TZVP Geometry N 1.38127 -0.94454 0.69704 C 0.37800 0.10873 0.74310 C 0.98671 1.29880 -0.04828 C 2.40860 0.83254 -0.37842 C 2.24529 -0.67842 -0.45329 C -0.94168 -0.31983 0.13001 O -1.87408 0.63009 0.26682 O -1.14355 -1.37231 -0.41287 C -3.15104 0.32164 -0.28926 H 0.93787 -1.85314 0.63247 H 0.16415 0.39766 1.77532 H 0.42208 1.46541 -0.96687 H 0.95547 2.22275 0.52417 H 2.78953 1.26968 -1.29997 H 3.09064 1.08271 0.43480 H 3.18669 -1.21878 -0.35652 H 1.77753 -0.95935 -1.40718 H -3.56331 -0.56909 0.18245 H -3.06476 0.14588 -1.36060 H -3.77896 1.18505 -0.09210 Proline M06-2X/def2-TZVP Geometry N 0.82438 -0.94722 0.76825 C -0.08539 0.18427 0.69389 C 0.68199 1.28455 -0.09162 C 2.06729 0.67132 -0.32728 C 1.76794 -0.82055 -0.34263 C -1.38377 -0.15927 -0.00690 O -2.24351 0.87465 0.00258 O -1.64461 -1.21445 -0.51463 H 0.31177 -1.82029 0.73169 H -0.35597 0.53556 1.69306 H 0.18677 1.48127 -1.04327 H 0.71356 2.22249 0.45739 H 2.53013 1.02557 -1.24683 H 2.73121 0.89786 0.50734 H 2.64818 -1.43844 -0.16752 H 1.32575 -1.10671 -1.30700 H -3.04540 0.58974 -0.45896 Tetrazole-derived amine M06-2X/def2-TZVP Geometry N -1.24543 -1.04699 -0.51683 C -0.58251 0.26609 -0.63302 C -1.35269 1.20515 0.31447 C -2.75778 0.61117 0.30354 C -2.45453 -0.88533 0.31366 C 0.86213 0.15555 -0.27457 N 1.43310 -0.96620 0.17253 N 2.72070 -0.72411 0.43007 N 2.91443 0.50652 0.14612 N 1.77893 1.09017 -0.29739 H -1.48932 -1.39678 -1.43222 H -0.64413 0.65123 -1.65393 H -0.92520 1.14263 1.31730 H -1.29326 2.24127 -0.01037 H -3.36402 0.93220 1.14927 H -3.27861 0.88442 -0.61726 H -3.26539 -1.50151 -0.07197 H -2.24189 -1.21654 1.33324 H 1.00199 -1.86842 0.29995 Benzimidazole-derived amine M06-2X/def2-TZVP Geometry N 3.33920 0.98125 -0.62569 C 2.74917 -0.35979 -0.79242 C 3.43962 -1.24915 0.24803 C 3.71725 -0.24982 1.36832 C 4.16763 0.98932 0.59754 C 1.26398 -0.30533 -0.55249 N 0.61679 0.88900 -0.44322 C -0.71640 0.60914 -0.24605 C -0.78772 -0.79132 -0.25097 N 0.47162 -1.33396 -0.44253 C -1.84192 1.40489 -0.06467 C -3.06289 0.77658 0.11215 C -3.15293 -0.63894 0.10829 C -2.02179 -1.41444 -0.07155 C -4.49294 -1.29604 0.30155 C -4.30608 1.60028 0.30948 H 3.87702 1.24595 -1.43715 H 2.90748 -0.73095 -1.80676 H 2.81295 -2.08862 0.54014 H 4.37921 -1.62858 -0.15913 H 2.79377 -0.03974 1.91282 H 4.46413 -0.59070 2.08298 H 5.23241 0.91135 0.35590 H 4.01722 1.91099 1.16040 H 1.09899 1.77229 -0.47804 H -1.77625 2.48616 -0.06182 H -2.08594 -2.49559 -0.07479 H -4.39834 -2.38038 0.27663 H -4.94081 -1.01770 1.25841 H -5.19950 -1.00049 -0.47764 H -5.04615 1.39691 -0.46794 H -4.78321 1.37840 1.26686 H -4.07608 2.66445 0.28599 Amine 24 M06-2X/def2-TZVP Geometry N 1.51164 2.59190 -0.16026 C 0.23673 1.96747 0.18448 C -0.78763 3.05431 -0.19336 C 0.01883 4.37247 -0.21683 C 1.40014 3.96814 0.30357 C 0.06240 0.64133 -0.56158 C -1.29844 -0.00068 -0.37510 C 1.18730 -0.31320 -0.19997 C 1.16047 -1.03159 0.99579 C 2.21323 -1.85745 1.36058 C 3.31012 -1.96247 0.50442 C 3.36323 -1.26408 -0.69237 C 2.29077 -0.43795 -1.03126 C -1.76621 -0.86152 -1.36984 C -2.98401 -1.51138 -1.25463 C -3.75092 -1.29166 -0.10923 C -3.31629 -0.44461 0.89695 C -2.08367 0.19594 0.75127 C 4.53944 -1.39466 -1.62111 C 2.17815 -2.64338 2.64289 C -3.48482 -2.43050 -2.33468 C -4.14717 -0.20368 2.12790 H 2.29706 2.09549 0.24387 H 0.18074 1.77700 1.26841 H -1.21660 2.83721 -1.17257 H -1.61198 3.08489 0.51703 H 0.10590 4.74394 -1.23700 H -0.43486 5.15668 0.38715 H 1.42247 4.04186 1.40142 H 2.20661 4.58267 -0.09605 H 0.17061 0.88507 -1.62251 H 0.29485 -0.95280 1.64491 H 4.13764 -2.60805 0.78110 H 2.32417 0.12998 -1.95522 H -1.15355 -1.02686 -2.25034 H -4.70740 -1.79426 -0.00703 H -1.74754 0.85668 1.54239 H 4.91548 -0.41419 -1.91657 H 5.35328 -1.94684 -1.15304 H 4.25501 -1.92246 -2.53361 H 2.12250 -3.71459 2.43955 H 3.07940 -2.47020 3.23308 H 1.31524 -2.37076 3.24875 H -3.71210 -3.41842 -1.93086 H -4.40202 -2.04194 -2.78132 H -2.74637 -2.54829 -3.12632 H -3.58780 -0.45159 3.03162 H -4.43701 0.84617 2.20218 H -5.05521 -0.80480 2.11548 Amine 25 M06-2X/def2-TZVP Geometry N 1.53463 1.06523 -0.34587 C 1.22098 -0.35655 -0.53443 C 2.54032 -1.09908 -0.22738 C 3.56307 0.01527 0.03193 C 2.68621 1.14837 0.54741 C 0.08992 -0.82953 0.37531 N -1.11546 -0.04312 0.21483 C -2.16612 -0.40024 1.15705 C -3.39024 0.34960 0.63366 C -3.14169 0.44933 -0.89004 C -1.74957 -0.16276 -1.09322 H 0.72055 1.55789 0.00389 H 0.92386 -0.52123 -1.57361 H 2.41873 -1.71284 0.66873 H 2.83950 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