Version2.4 2021-05-06T09:01:32Z 10.1021/jm300687e Gaussian16 RevisionB.01 RPOIRIER 11-Apr-2019 #N HF/6-31G(d) OPT=(MaxStep=1) FREQ IOp(6/10=2,6/11=2,6/12=2) DUDE Cc1ccc(c2c1[C@H]3C=CC[C@@H]3[C@@H](N2)c4ccc(cc4O)O)O C13639812 RHF 6-31G(d) (6D,7F) Cc1ccc(c2c1[C@H]3C=CC[C@@H]3[C@@H](N2)c4ccc(cc4O)O)O C01[X(C19H19N1O3)] 120 C1 383 Oc1ccc(c(c1)O)[C@@H]1Nc2c(O)ccc(c2[C@@H]2[C@@H]1CC=C2)C Oc1ccc(c(c1)O)[C@@H]1Nc2c(O)ccc(c2[C@@H]2[C@@H]1CC=C2)C Cc1ccc(O)c2N[C@H]([C@H]3CC=C[C@@H]3c12)c4ccc(O)cc4O InChIKey=PWFMNUCQOKMLRP-ZJNRKIDTSA-N InChI=1S/C19H19NO3/c1-10-5-8-15(22)19-17(10)12-3-2-4-13(12)18(20-19)14-7-6-11(21)9-16(14)23/h2-3,5-9,12-13,18,20-23H,4H2,1H3/t12-,13-,18+/m0/s1 InChI=1/C19H19NO3/c1-10-5-8-15(22)19-17(10)12-3-2-4-13(12)18(20-19)14-7-6-11(21)9-16(14)23/h2-3,5-9,12-13,18,20-23H,4H2,1H3/t12-,13-,18+/m0/s1 Cc1ccc(c2c1[C@H]3C=CC[C@@H]3[C@@H](N2)c4ccc(cc4O)O)O C01[X(C19H19N1O3)] 120 C01 383 Oc1ccc(c(c1)O)[C@@H]1Nc2c(O)ccc(c2[C@@H]2[C@@H]1CC=C2)C O[C]1[CH][CH][C]([C]([CH]1)O)[C@@H]1N[C]2[C]([CH][CH][C]([C]2[C@@H]2[C@@H]1CC=C2)C)O C[C]1[CH][CH][C](O)[C]2N[C@@H]([C]3[CH][CH][C](O)[CH][C]3O)[C@H]4CC=C[C@@H]4[C]12 InChIKey=PWFMNUCQOKMLRP-ZJNRKIDTSA-N InChI=1S/C19H19NO3/c1-10-5-8-15(22)19-17(10)12-3-2-4-13(12)18(20-19)14-7-6-11(21)9-16(14)23/h2-3,5-9,12-13,18,20-23H,4H2,1H3/t12-,13-,18+/m0/s1 InChI=1/C19H19NO3/c1-10-5-8-15(22)19-17(10)12-3-2-4-13(12)18(20-19)14-7-6-11(21)9-16(14)23/h2-3,5-9,12-13,18,20-23H,4H2,1H3/t12-,13-,18+/m0/s1 1921.5972162851 -1009.5538376 1-A 7671.0872 82 301 383 |A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A| -20.59604 -20.59358 -20.58592 -15.54761 -11.30218 -11.30191 -11.27863 -11.25781 -11.25597 -11.23227 -11.22432 -11.22421 -11.22119 -11.21915 -11.21896 -11.21787 -11.21746 -11.21685 -11.21461 -11.21259 -11.21104 -11.21084 -11.21069 -1.41564 -1.41221 -1.40149 -1.23680 -1.14667 -1.13615 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0.9335 1.6030 1.9830 2.1581 1.1993 1.8758 2.1522 2.2633 2.1351 2.5102 1.2756 1.5786 1.4046 1.4417 1.6449 1.6277 2.0542 1.6506 1.5722 2.1470 2.9076 2.2362 1.9216 2.0547 2.6500 2.1852 1.8844 2.2609 1.9497 2.1150 2.1983 2.1054 1.8103 4.9328 4.6326 1.6602 2.5075 2.0092 1.8794 3.5904 5.0461 12.5713 11.7404 10.2568 12.1065 12.7786 6.3234 6.5688 6.3027 6.4825 6.6728 6.8937 6.9309 6.9908 7.1514 7.2169 7.2900 7.3066 7.3218 7.4832 7.6133 9.4189 10.6458 10.6475 10.7014 0.0858 0.4623 0.0996 0.3122 0.7683 0.3603 1.5014 2.5933 25.8133 34.2149 81.4161 6.2359 0.1227 0.3542 1.3747 3.0496 6.1064 249.9508 4.4715 9.1743 2.7548 6.9524 1.4089 2.6089 3.6635 5.5964 6.4310 3.8289 3.7480 16.1103 6.9499 36.7983 5.2946 15.8481 32.5253 9.5688 20.5007 4.4006 12.0996 0.7063 6.0167 4.8972 0.7982 4.3873 58.1198 30.9357 20.8066 67.8101 1.1237 25.0305 0.9251 11.6719 9.5173 44.6028 1.4764 3.4764 9.2329 1.9067 19.4189 1.7027 30.9727 46.1596 48.1273 49.7531 82.5304 5.9540 36.7950 12.8663 49.6554 16.9814 18.7443 20.9957 258.2190 25.1031 59.1219 24.8365 7.6552 75.9080 106.3378 107.4061 108.9740 3.0918 125.2900 3.5563 3.2803 23.3642 62.7477 1.3880 42.0036 81.5720 6.2987 15.3934 6.6742 44.8031 139.2279 98.6294 46.0913 85.9395 27.6343 198.8603 3.1353 19.6390 20.6180 40.6193 45.6222 34.4437 49.2840 31.4246 42.0095 24.9476 24.2484 10.9076 30.0342 27.8139 3.6623 21.8277 38.0511 110.2434 88.2592 102.7464 2.8098 6.7736 4.2868 1.0770 1.4940 1.0256 0.6786 1.1335 2.0434 0.9920 2.3385 1.3473 0.3717 1.3471 2.1956 2.6824 0.5370 3.7857 1.8141 2.3719 3.1006 4.3342 2.4722 1.8760 4.8068 1.7857 2.1299 2.9760 5.9315 1.6162 6.8311 0.2503 0.4816 0.4275 7.1018 0.2239 7.1867 6.1424 1.8879 11.9429 10.0017 2.9372 5.7231 7.0763 8.4664 3.5669 2.9556 2.7082 1.5304 2.6450 1.2199 4.3387 8.5071 4.8965 0.8809 0.7417 3.5064 2.3244 13.2111 1.1282 2.4965 3.5723 1.0011 1.0389 11.1281 8.8773 14.9207 3.2995 7.1269 6.3691 2.7372 2.4204 2.3414 12.8700 11.9158 2.8480 15.2666 5.8304 4.1326 18.5095 18.0453 2.6531 4.4708 1.5212 6.9478 2.7393 1.3551 10.6764 8.5683 1.4213 21.5012 1.5839 12.5108 8.4824 7.2215 0.5472 44.6432 7.6305 12.7706 48.2148 32.7312 74.3354 43.4930 126.6173 96.6218 92.9414 85.6010 65.3333 76.6395 109.0630 97.6169 116.4923 122.5177 204.4121 67.3588 100.8223 56.0548 94.8004 106.9618 126.6078 0.7472 0.7427 0.7394 0.7473 0.7476 0.7377 0.7175 0.2079 0.5970 0.5067 0.5720 0.7467 0.7411 0.7245 0.4165 0.6544 0.5604 0.7404 0.6377 0.7388 0.7464 0.6101 0.3279 0.5116 0.2903 0.2154 0.6313 0.5792 0.0784 0.2837 0.4456 0.7464 0.2121 0.4656 0.1605 0.3672 0.2257 0.5454 0.5856 0.4170 0.1414 0.1511 0.0966 0.0832 0.3186 0.5371 0.6045 0.7272 0.7187 0.4324 0.7257 0.2075 0.1373 0.0957 0.3468 0.6030 0.4152 0.5251 0.4017 0.6314 0.5280 0.4977 0.6341 0.3435 0.6661 0.6645 0.6080 0.6485 0.7075 0.6866 0.4462 0.3657 0.3101 0.2538 0.0711 0.7202 0.3389 0.2617 0.2953 0.4990 0.0867 0.7227 0.1468 0.7321 0.6242 0.7214 0.6936 0.5000 0.2896 0.5331 0.7452 0.7492 0.6575 0.7083 0.2465 0.7120 0.7063 0.6416 0.4412 0.5392 0.2186 0.1959 0.6914 0.0086 0.1408 0.1586 0.5836 0.6871 0.7292 0.4425 0.3494 0.2971 0.5760 0.1602 0.1947 0.1881 0.2010 0.3633 0.2469 0.2947 0.8553 0.8524 0.8501 0.8554 0.8556 0.8490 0.8355 0.3443 0.7476 0.6726 0.7278 0.8550 0.8513 0.8402 0.5880 0.7911 0.7183 0.8508 0.7788 0.8498 0.8548 0.7578 0.4939 0.6769 0.4500 0.3544 0.7740 0.7335 0.1453 0.4420 0.6165 0.8548 0.3499 0.6354 0.2765 0.5371 0.3682 0.7059 0.7387 0.5885 0.2478 0.2626 0.1761 0.1537 0.4832 0.6989 0.7535 0.8420 0.8363 0.6038 0.8410 0.3437 0.2414 0.1747 0.5150 0.7523 0.5868 0.6886 0.5731 0.7741 0.6911 0.6646 0.7761 0.5113 0.7996 0.7984 0.7563 0.7868 0.8287 0.8142 0.6171 0.5355 0.4734 0.4049 0.1328 0.8373 0.5062 0.4148 0.4559 0.6658 0.1595 0.8390 0.2560 0.8453 0.7687 0.8381 0.8191 0.6667 0.4491 0.6955 0.8540 0.8566 0.7934 0.8292 0.3955 0.8318 0.8279 0.7817 0.6123 0.7006 0.3588 0.3276 0.8176 0.0170 0.2468 0.2738 0.7370 0.8145 0.8434 0.6135 0.5179 0.4581 0.7309 0.2761 0.3260 0.3167 0.3348 0.5330 0.3961 0.4552 298.150 1.00000 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 6 6 6 6 6 6 6 6 1 6 6 6 6 1 6 1 7 6 6 6 6 6 6 8 8 8 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 12.00000 12.00000 12.00000 12.00000 12.00000 12.00000 12.00000 12.00000 1.00783 12.00000 12.00000 12.00000 12.00000 1.00783 12.00000 1.00783 14.00307 12.00000 12.00000 12.00000 12.00000 12.00000 12.00000 15.99491 15.99491 15.99491 1.00783 1.00783 1.00783 1.00783 1.00783 1.00783 1.00783 1.00783 1.00783 1.00783 1.00783 1.00783 1.00783 1.00783 1.00783 1.00783 3875.6721 10755.5688 12498.0926 0.99997 0.00562 0.00459 -0.00562 0.99998 0.00060 -0.00459 -0.00062 0.99999 1 0.02235 0.00805 0.00693 0.46566 0.16780 0.14440 30.19 68.77 87.99 117.98 169.52 215.35 235.98 278.62 306.08 319.91 330.42 365.65 392.77 418.94 469.65 493.58 499.66 512.95 537.02 546.57 569.90 577.46 637.56 695.64 733.28 742.67 755.56 786.50 812.02 860.62 885.97 907.85 945.59 976.22 978.74 1028.21 1096.80 1133.66 1152.46 1156.47 1179.49 1185.00 1210.76 1240.40 1279.90 1286.66 1306.10 1342.56 1381.59 1432.77 1472.24 1474.74 1523.23 1541.91 1571.74 1574.39 1605.85 1621.59 1662.40 1681.74 1704.53 1722.61 1727.48 1764.06 1767.91 1782.84 1795.42 1859.49 1868.28 1875.97 1895.20 1905.41 1923.27 1948.59 1984.42 1991.53 2008.17 2059.48 2065.52 2084.79 2106.00 2113.85 2120.71 2152.64 2184.27 2204.76 2230.08 2261.59 2308.43 2336.84 2360.08 2362.66 2364.87 2386.35 2436.39 2443.36 2571.01 2592.50 2618.11 2629.19 2651.70 4532.36 4610.67 4619.25 4631.79 4643.47 4686.62 4702.06 4719.44 4800.95 4819.50 4841.38 4848.47 4849.00 4905.47 4935.67 5545.36 5921.58 5921.98 5936.66 0.370593 0.388887 0.389831 0.324240 -1009.183245 -1009.164951 -1009.164006 -1009.229598 2.199966D-04 MUNgauss RevisionA2.1 retrievium 06-May-2021 DUDE Cc1ccc(c2c1[C@H]3C=CC[C@@H]3[C@@H](N2)c4ccc(cc4O)O)O C13639812 RHF 6-31G(d) (6D,10F) C1 309.136494 |X|Y|Z| 40.712364 26.565845 72.854948 42.871598 19 6 7 18 1 |36.858105| |12.580194|36.858105| |7.663033|13.745954|36.858105| |5.037808|7.875582|13.745587|36.858105| |4.425006|6.821753|7.981247|13.867615|36.858105| |4.965758|7.865637|6.896653|7.938463|13.655963|36.858105| |7.421095|13.593699|7.943733|6.840940|7.875013|13.627080|36.858105| |5.985144|7.235220|4.940084|4.437492|5.105558|7.890174|12.532057|36.858105| |5.061264|5.924800|4.375041|4.063217|4.726849|6.986710|9.030599|17.450346|0.500000| |6.112428|5.811149|4.098231|3.530109|3.758153|4.962972|7.084730|12.558792|0.250041|36.858105| |4.393857|4.289263|3.303333|2.979103|3.225490|4.137873|5.168962|8.128158|0.184569|14.430027|36.858105| |3.673293|3.925283|3.156643|3.002938|3.420436|4.502888|5.067377|7.776708|0.183709|8.079461|12.603625|36.858105| |4.300572|5.121994|4.011065|3.895443|4.709445|7.002064|7.703440|12.319552|0.244634|8.049711|8.091348|12.407330|36.858105| |4.440790|5.356831|4.271633|4.137596|4.904874|6.893317|7.526094|9.026160|0.176236|6.953688|6.946894|9.007589|17.539654|0.500000| |3.504091|4.333768|3.709816|3.915481|5.150977|7.583993|6.311175|7.476174|0.197026|5.081480|5.033952|7.128264|12.405425|0.250041|36.858105| |3.115759|3.785292|3.376686|3.631988|4.702741|6.164149|5.092140|5.573445|0.142087|4.243073|4.383585|6.198472|8.957594|0.232899|17.564801|0.500000| |3.810584|5.139485|4.583005|5.202157|7.931633|13.645593|7.828973|7.084184|0.194034|4.569266|4.120578|4.952559|7.873232|0.191128|13.014766|0.253182|53.358707| |2.939206|3.437326|3.004478|3.143852|3.933039|5.170765|4.597973|5.631527|0.173465|4.303858|4.429869|6.124470|7.346198|0.153343|12.492992|0.250477|10.600006|36.858105| |2.865787|3.322905|2.934380|3.067015|3.775398|4.795222|4.320286|5.103094|0.175425|3.952465|3.865829|4.726536|5.461054|0.119116|7.452600|0.158437|9.100852|13.769748|36.858105| |2.424456|2.709588|2.440498|2.531574|2.992882|3.565657|3.318906|3.840164|0.127669|3.245573|3.255502|3.834572|4.036281|0.092648|4.957667|0.117627|6.155695|7.835911|13.718481|36.858105| |2.162776|2.376755|2.153589|2.226172|2.595827|3.038508|2.857674|3.318319|0.104533|2.931962|3.071312|3.700964|3.668452|0.086146|4.398872|0.111484|5.153453|6.788868|7.975604|13.787308|36.858105| |2.186726|2.409396|2.173946|2.248267|2.637491|3.117327|2.923396|3.439266|0.103754|3.057518|3.324322|4.261419|4.095108|0.096504|4.986868|0.132920|5.370747|7.839049|6.922275|7.942575|13.731618|36.858105| |2.495838|2.812217|2.503012|2.599946|3.128332|3.843427|3.541843|4.260068|0.125156|3.626108|3.977119|5.580555|5.591835|0.127259|7.512212|0.201529|7.006787|13.620337|8.039962|6.896393|7.957946|13.785448|36.858105| |2.422806|2.709480|2.425574|2.512635|2.986290|3.602415|3.351895|3.960252|0.108828|3.498243|3.983775|5.807645|5.541571|0.135790|6.819934|0.219400|6.267747|8.098083|5.296384|4.628427|5.237636|8.012523|14.072680|73.516695| |1.898463|2.050225|1.880803|1.936088|2.208485|2.511534|2.392034|2.719326|0.084381|2.483945|2.601142|3.010277|2.929694|0.070919|3.354466|0.087358|4.080868|4.584851|5.224538|7.939103|14.109963|8.158147|5.286339|7.186383|73.516695| |3.360314|4.583937|5.207314|7.911922|13.959681|8.107628|5.236274|4.006411|0.107274|3.081727|2.768706|3.025553|3.993293|0.114039|4.754404|0.127685|9.670436|3.820176|3.680135|2.977109|2.607105|2.649024|3.108770|5.276904|3.963365|73.516695| |17.572682|8.782566|5.944703|4.300137|3.936178|4.498908|6.509697|5.912171|0.132303|6.853530|4.997715|3.984026|4.487941|0.133270|3.486833|0.087610|4.905697|2.902656|2.755705|2.344325|2.130114|2.189001|2.513075|4.426039|3.327308|5.481159|0.500000| |17.555857|8.788177|5.913797|4.293990|3.944479|4.526425|6.579948|6.014205|0.152057|6.469731|4.506128|3.660831|4.137687|0.112434|3.396366|0.082415|4.962947|2.959792|2.963957|2.531865|2.237186|2.228174|2.508609|4.250704|3.501990|5.492866|0.301878|0.500000| |17.581312|8.895710|7.495450|4.850963|4.011624|4.175365|5.537661|4.493956|0.110603|4.558407|3.544964|3.050296|3.493599|0.101245|2.978249|0.075261|4.446520|2.546196|2.503229|2.158967|1.939864|1.953650|2.199268|3.813520|3.066387|5.556360|0.302672|0.303030|0.500000| |7.172881|8.935538|17.718989|8.962299|5.680156|4.964482|5.644973|4.008728|0.100658|3.567306|2.932326|2.753747|3.334276|0.098539|3.077032|0.079200|4.956425|2.575086|2.532969|2.161178|1.928511|1.941054|2.198519|3.810690|3.037546|7.479599|0.156023|0.154486|0.235228|0.500000| |4.116655|5.616866|8.895169|17.678180|8.951605|5.640423|4.932303|3.547805|0.092209|2.948425|2.554416|2.579871|3.220870|0.094892|3.291360|0.087062|5.727034|2.735815|2.689057|2.276932|2.023984|2.038066|2.319030|4.006783|3.172391|12.701732|0.099937|0.099676|0.115660|0.216094|0.500000| |7.166161|5.788709|4.085000|3.385358|3.441794|4.293354|6.099377|8.287213|0.193519|17.784141|9.006687|5.628752|5.601251|0.143816|4.021961|0.096052|5.212494|3.535265|3.387188|2.876981|2.598693|2.655570|3.042340|5.205810|4.007097|5.015454|0.227607|0.233321|0.145627|0.102223|0.079518|0.500000| |3.852800|3.599771|2.871498|2.588723|2.743912|3.364470|4.068648|5.634830|0.137911|8.966076|17.707319|8.354760|5.627402|0.143913|3.975283|0.100185|4.554546|3.665394|3.277573|2.883992|2.785983|3.006863|3.456840|6.251504|4.309868|4.265246|0.123391|0.110826|0.089411|0.072722|0.062899|0.209054|0.500000| |3.221709|3.427221|2.824481|2.727649|3.120612|4.028279|4.354743|6.416830|0.175872|6.427163|8.896363|17.540487|8.675449|0.175066|6.665470|0.158114|6.314857|7.007771|5.436940|4.528300|4.475223|5.239202|6.782901|11.539742|6.315834|5.035907|0.094265|0.091632|0.075671|0.069054|0.065925|0.134847|0.194320|0.500000| |3.241768|3.437913|2.865643|2.759369|3.113282|3.915068|4.230333|5.657653|0.135126|5.945634|8.719507|17.563760|8.695202|0.225544|6.038683|0.165929|5.838478|5.204537|3.986992|3.363583|3.379882|4.028681|5.226916|10.943471|4.997623|5.011571|0.099112|0.087884|0.076770|0.070456|0.066967|0.126545|0.200757|0.302984|0.500000| |3.278805|4.307910|4.125826|4.964803|7.719322|9.521620|5.816530|5.173665|0.143654|3.693659|3.424121|4.078633|5.799447|0.150732|9.207270|0.229137|26.037513|6.744968|5.986921|4.302542|3.667042|3.814699|4.841690|7.798021|5.233043|15.373868|0.086241|0.086870|0.080636|0.093317|0.116963|0.088757|0.079871|0.108488|0.102749|0.500000| |3.168715|3.769258|3.324783|3.492953|4.355218|5.616150|4.973166|5.581039|0.203945|4.110496|3.788183|4.363563|5.347530|0.118547|6.944336|0.144367|10.336846|9.005085|17.758388|8.954458|5.675522|4.981089|5.698994|7.590852|7.493464|7.374201|0.082398|0.091768|0.076578|0.078644|0.083910|0.099531|0.088565|0.131593|0.101296|0.182657|0.500000| |2.325392|2.573102|2.343735|2.424839|2.814096|3.261941|3.068640|3.450713|0.115502|2.967307|2.912992|3.272820|3.448535|0.081017|4.053577|0.097417|5.365019|5.604165|8.885584|17.694819|8.900650|5.639339|4.962447|6.522466|12.683195|4.980944|0.061764|0.068181|0.058101|0.058202|0.061144|0.075029|0.072725|0.104453|0.080206|0.105342|0.215718|0.500000| |1.980372|2.152481|1.959117|2.019509|2.330933|2.695187|2.553245|2.959642|0.087229|2.717461|2.996369|3.760293|3.504362|0.085464|4.068876|0.113152|4.485783|5.590337|4.976832|5.657750|8.943970|17.707617|8.875287|12.820179|13.334589|4.180740|0.055494|0.055856|0.049590|0.049111|0.051372|0.066432|0.077288|0.125469|0.102965|0.089596|0.107990|0.124233|0.500000| 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