Version2.4 2021-05-07T05:28:48Z 10.1021/jm300687e Gaussian16 RevisionB.01 RPOIRIER 08-Apr-2019 #N HF/6-31G(d) OPT=(MaxStep=1) FREQ IOp(6/10=2,6/11=2,6/12=2) DUDE c1ccc(c(c1)C(=O)NNC(=O)c2c[nH]c3c2ccc(c3)Cl)O C64354361 RHF 6-31G(d) (6D,7F) c1ccc(c(c1)C(=O)NNC(=O)c2c[nH]c3c2ccc(c3)Cl)O C01[X(C16H12Cl1N3O3)] 99 C1 373 Clc1ccc2c(c1)[nH]cc2C(=O)NNC(=O)c1ccccc1O Clc1ccc2c(c1)[nH]cc2C(=O)NNC(=O)c1ccccc1O Oc1ccccc1C(=O)NNC(=O)c2c[nH]c3cc(Cl)ccc23 InChIKey=UUJGVPATBIUSGK-UHFFFAOYSA-N InChI=1S/C16H12ClN3O3/c17-9-5-6-10-12(8-18-13(10)7-9)16(23)20-19-15(22)11-3-1-2-4-14(11)21/h1-8,18,21H,(H,19,22)(H,20,23) InChI=1/C16H12ClN3O3/c17-9-5-6-10-12(8-18-13(10)7-9)16(23)20-19-15(22)11-3-1-2-4-14(11)21/h1-8,18,21H,(H,19,22)(H,20,23)/f/h19-20H c1ccc(c(c1)C(=O)NNC(=O)c2c[nH]c3c2ccc(c3)Cl)O C01[X(C16H12Cl1N3O3)] 99 C01 373 Clc1ccc2c(c1)[nH]cc2C(=O)NNC(=O)c1ccccc1O O=C([C]1=CN[C]2[C]1[CH][CH][C]([CH]2)Cl)NN[C]([O])[C]1[CH][CH][CH][CH][C]1O [O][C](NNC(=O)C1=CN[C]2[CH][C](Cl)[CH][CH][C]12)[C]3[CH][CH][CH][CH][C]3O InChIKey=UUJGVPATBIUSGK-UHFFFAOYSA-N InChI=1S/C16H12ClN3O3/c17-9-5-6-10-12(8-18-13(10)7-9)16(23)20-19-15(22)11-3-1-2-4-14(11)21/h1-8,18,21H,(H,19,22)(H,20,23) InChI=1/C16H12ClN3O3/c17-9-5-6-10-12(8-18-13(10)7-9)16(23)20-19-15(22)11-3-1-2-4-14(11)21/h1-8,18,21H,(H,19,22)(H,20,23)/f/h19-20H 1836.1098296182 -1460.309842 1-A 13704.7096 85 288 373 |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|A|A|A| -104.82560 -20.58514 -20.55510 -20.54837 -15.63864 -15.63583 -15.63145 -11.38004 -11.37348 -11.32125 -11.30865 -11.30564 -11.28994 -11.25975 -11.25472 -11.25452 -11.25156 -11.24848 -11.24760 -11.24603 -11.24122 -11.23510 -11.23254 -10.55897 -8.02837 -8.02505 -8.02501 -1.44379 -1.42088 -1.40487 -1.33648 -1.32412 -1.18766 -1.17448 -1.14919 -1.11922 -1.08135 -1.04322 -1.02798 -1.02134 -0.98724 -0.90693 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329.05672 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 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 |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|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A| 8.1326 27.8690 40.3680 44.5926 66.3506 97.9169 108.2041 155.0041 166.3330 188.7736 232.3784 256.8273 278.4893 280.5098 319.0592 351.8143 368.9815 401.4747 443.3911 457.8528 468.3918 475.2519 477.0128 489.3619 495.4039 532.9010 568.6984 584.4923 604.6133 614.7195 655.4818 676.3775 686.8303 717.2193 731.1314 770.6383 779.6608 818.3655 848.3198 849.7875 860.5724 871.6117 897.8318 919.3050 933.7489 972.8389 973.4529 990.1374 992.4083 1008.3196 1083.4979 1104.7470 1121.6094 1130.3129 1144.7801 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6.2368 3.2819 2.6367 5.8837 5.8167 8.4099 9.8366 1.0881 1.0909 1.0940 1.0956 1.0910 1.0974 1.0959 1.0991 1.0788 1.0782 1.0817 1.0664 0.0003 0.0028 0.0071 0.0089 0.0171 0.0499 0.0523 0.0949 0.1102 0.1296 0.1566 0.3089 0.2389 0.2919 0.5109 0.3835 0.4361 0.5880 0.8453 0.6184 0.3064 0.2577 0.3794 0.5598 0.2643 0.5098 0.4311 0.6477 0.5552 1.4377 1.0120 1.0907 1.0837 0.3327 1.9076 2.0777 1.6620 2.3118 0.7688 1.8943 2.3980 1.1989 2.4638 3.1276 0.7398 0.8202 0.8328 1.3703 1.2797 4.0346 0.9352 0.9504 0.9818 2.2890 2.7647 1.7380 2.7462 2.2935 1.3525 1.6798 1.5988 2.6884 1.6159 2.2981 3.2473 1.8687 2.8094 2.5044 2.6835 3.6920 2.3958 3.2524 1.8600 4.1129 4.1942 3.7819 4.2433 4.6619 3.6805 7.7555 11.4774 6.0926 4.9014 11.3992 11.3678 17.3839 21.6648 7.2731 7.3436 7.4347 7.4456 7.4284 7.4866 7.5628 7.6970 9.4337 9.5446 9.7535 9.6884 1.8927 2.1795 2.1717 1.3398 4.8875 3.4583 1.2246 0.1201 7.1807 4.9358 1.7848 7.3659 1.5164 16.1830 38.0620 53.9374 6.1053 44.2117 13.3243 4.7350 91.1782 113.8757 1.1617 9.0731 35.5715 37.6492 40.7576 9.1409 36.1044 5.5796 23.1674 3.6663 21.7205 121.9566 19.6897 11.9746 13.9864 28.4229 103.0457 25.0740 25.2542 4.1562 33.0934 50.5847 48.4155 19.5608 13.1490 30.3713 12.9765 17.7592 2.1323 0.2924 0.9236 10.1450 61.6214 33.6202 6.5364 78.6805 78.7246 151.0046 33.7419 41.9724 63.1191 43.4708 42.8188 11.8869 48.0192 22.2437 51.5768 80.0173 2.6287 16.8750 179.4816 7.5173 335.9619 680.6473 176.7416 7.0900 129.4544 251.2105 4.9448 23.8215 42.6335 106.9722 23.5071 539.5201 147.5936 2.8623 17.0985 2.0546 19.0261 2.5723 9.6530 1.6570 0.2005 53.4384 154.6942 130.4416 341.0215 6.9308 4.5156 5.6317 0.3875 1.2482 1.0807 0.9821 1.7811 2.5875 1.0149 0.1833 1.4880 0.7072 2.7437 1.3841 0.7225 0.9759 4.7164 8.1243 0.8634 1.3470 0.7352 0.4141 0.9858 5.8536 0.9078 3.7962 0.6809 1.9045 7.2979 3.3641 0.3046 3.8384 1.4693 4.9524 7.7881 5.4987 0.1704 1.7732 5.4189 11.7521 0.4239 10.8620 10.7107 0.7562 0.6996 3.2406 1.4165 3.2158 8.1798 1.6714 0.1181 0.1469 17.4650 1.2772 11.5862 14.2173 6.8070 3.2753 3.9057 3.6678 44.1715 1.9415 11.8578 26.0284 0.8056 44.9234 11.2950 39.7179 21.1786 55.7495 40.6994 34.8266 62.3906 42.9413 3.2913 31.1102 13.4060 5.3175 127.5439 20.0426 7.3090 16.4167 36.6672 41.9645 40.2726 116.6688 65.8157 76.6691 87.4013 52.3024 70.8445 250.6053 88.7924 74.6931 53.3245 30.9870 114.5041 55.1610 0.7460 0.7438 0.7493 0.7244 0.7439 0.7468 0.7370 0.4942 0.7432 0.3920 0.7349 0.6109 0.6886 0.7328 0.6587 0.7431 0.6344 0.4787 0.3295 0.7214 0.7500 0.5360 0.7482 0.5776 0.7328 0.7498 0.6741 0.4813 0.1762 0.6797 0.7255 0.6936 0.6428 0.5157 0.1284 0.1276 0.1496 0.7460 0.7490 0.3013 0.1009 0.7500 0.3476 0.1044 0.7485 0.7215 0.7238 0.7440 0.5230 0.0904 0.0989 0.6970 0.5559 0.1342 0.2363 0.1383 0.2718 0.6588 0.3632 0.3525 0.5655 0.3307 0.4261 0.6622 0.2043 0.7195 0.1684 0.7470 0.2310 0.1362 0.1834 0.4954 0.3968 0.7406 0.6114 0.3028 0.2053 0.2737 0.3835 0.2495 0.4341 0.4829 0.2377 0.6214 0.6755 0.3374 0.2266 0.6354 0.7344 0.2797 0.4284 0.4727 0.1299 0.1704 0.3344 0.1435 0.1550 0.2182 0.2000 0.8545 0.8531 0.8567 0.8402 0.8531 0.8551 0.8486 0.6615 0.8527 0.5632 0.8472 0.7585 0.8156 0.8458 0.7942 0.8526 0.7763 0.6475 0.4957 0.8381 0.8571 0.6979 0.8560 0.7323 0.8458 0.8570 0.8053 0.6498 0.2996 0.8093 0.8409 0.8191 0.7825 0.6805 0.2275 0.2264 0.2603 0.8545 0.8565 0.4631 0.1832 0.8571 0.5159 0.1891 0.8561 0.8382 0.8397 0.8532 0.6868 0.1659 0.1800 0.8215 0.7146 0.2367 0.3823 0.2430 0.4274 0.7943 0.5329 0.5213 0.7224 0.4970 0.5976 0.7968 0.3392 0.8369 0.2883 0.8552 0.3753 0.2398 0.3100 0.6626 0.5682 0.8510 0.7588 0.4648 0.3407 0.4298 0.5544 0.3993 0.6054 0.6513 0.3841 0.7665 0.8063 0.5046 0.3695 0.7771 0.8469 0.4371 0.5998 0.6419 0.2300 0.2912 0.5012 0.2510 0.2684 0.3582 0.3334 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 6 6 6 6 6 6 6 8 7 7 6 8 6 6 7 1 6 6 6 6 6 6 17 8 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 15.99491 14.00307 14.00307 12.00000 15.99491 12.00000 12.00000 14.00307 1.00783 12.00000 12.00000 12.00000 12.00000 12.00000 12.00000 34.96885 15.99491 1.00783 1.00783 1.00783 1.00783 1.00783 1.00783 1.00783 1.00783 1.00783 1.00783 1.00783 2329.1837 24115.4987 25182.5146 0.99998 0.00670 -0.00166 -0.00669 0.99996 0.00583 0.00170 -0.00582 0.99998 1 0.03719 0.00359 0.00344 0.77484 0.07484 0.07167 11.70 40.10 58.08 64.16 95.46 140.88 155.68 223.02 239.32 271.60 334.34 369.52 400.68 403.59 459.06 506.18 530.88 577.63 637.94 658.75 673.91 683.78 686.32 704.08 712.78 766.73 818.23 840.95 869.90 884.44 943.09 973.16 988.20 1031.92 1051.93 1108.78 1121.76 1177.45 1220.54 1222.65 1238.17 1254.05 1291.78 1322.67 1343.46 1399.70 1400.58 1424.59 1427.85 1450.75 1558.91 1589.48 1613.75 1626.27 1647.08 1695.33 1712.98 1752.07 1753.52 1775.00 1799.90 1848.39 1887.23 1901.14 1945.18 1971.86 1989.07 1999.73 2064.05 2081.34 2103.58 2153.46 2190.84 2248.36 2319.36 2327.69 2338.19 2388.29 2391.65 2466.47 2542.78 2553.91 2555.64 2609.03 2620.42 2694.92 2781.78 4846.20 4863.27 4886.33 4886.38 4890.99 4895.84 4924.15 4960.24 5543.06 5576.95 5628.54 5649.94 0.280680 0.298730 0.299674 0.230676 -1460.029162 -1460.011112 -1460.010168 -1460.079166 2.314204D-04 MUNgauss RevisionA2.1 retrievium 07-May-2021 DUDE c1ccc(c(c1)C(=O)NNC(=O)c2c[nH]c3c2ccc(c3)Cl)O C64354361 RHF 6-31G(d) (6D,10F) C1 329.056719 |X|Y|Z| 32.106594 21.058657 110.591073 42.129049 19 6 7 16 3 |36.858105| |13.653767|36.858105| |7.911957|13.874455|36.858105| |6.816113|7.927322|13.639728|36.858105| |7.867670|6.849987|7.882794|13.598362|36.858105| |13.881518|7.992093|6.893996|7.898881|13.589700|36.858105| |5.031314|4.468346|5.054607|7.658685|12.848320|7.547889|36.858105| |3.979413|3.794410|4.495891|6.696909|8.024136|5.253047|15.633736|73.516695| |4.508556|3.783033|3.948460|5.177962|7.876195|6.662189|14.144372|15.247016|53.358707| |3.392246|2.981298|3.141749|3.958235|5.160401|4.482423|8.137848|12.998560|18.644754|53.358707| |3.011114|2.641631|2.716528|3.260046|4.075306|3.801126|5.473818|8.794092|11.096073|18.959816|36.858105| |3.181837|2.726191|2.725358|3.184656|4.018015|3.986449|4.956406|7.522435|9.942675|11.575318|15.821012|73.516695| |2.452921|2.215874|2.297197|2.701936|3.187003|2.959198|4.090382|7.162683|7.078767|10.804597|12.970553|14.370498|36.858105| |2.236028|2.054555|2.155046|2.534360|2.913944|2.662300|3.734059|6.924971|6.034458|8.916405|7.511483|9.399951|14.024583|36.858105| |1.941067|1.803420|1.883782|2.168282|2.429727|2.252201|2.972851|5.510215|4.625085|6.135630|5.217448|7.424567|8.566983|14.040596|53.358707| |1.797575|1.684579|1.764208|2.017337|2.227502|2.063342|2.686815|5.047912|4.068265|5.203620|4.178588|6.138480|5.999439|9.109589|26.101105|0.500000| |1.904328|1.762309|1.822398|2.072771|2.324427|2.192006|2.780323|5.010247|4.372810|5.586752|5.148201|7.854834|8.369739|8.545984|18.847455|0.250213|36.858105| |2.159369|1.968617|2.022325|2.315708|2.657653|2.524197|3.214544|5.613137|5.283188|6.896337|7.338782|11.286374|13.172169|8.469612|11.587932|0.165504|13.649723|36.858105| |2.105039|1.915259|1.942149|2.182526|2.488212|2.419234|2.893125|4.936322|4.697650|5.626846|5.787751|10.633047|7.263780|5.242490|7.295160|0.118671|7.907666|13.624465|36.858105| |1.835862|1.691625|1.713882|1.897273|2.116080|2.065059|2.403202|4.157343|3.764773|4.365860|4.102511|7.452934|5.010715|4.171706|6.325514|0.109398|6.945338|7.977949|13.866250|36.858105| |1.673615|1.557424|1.589552|1.759920|1.939754|1.874060|2.210126|3.904626|3.398404|3.981905|3.578094|6.169917|4.567484|4.202839|7.050999|0.126686|8.110491|6.907325|7.913010|13.591259|36.858105| |1.693112|1.579249|1.625610|1.818477|2.005646|1.911766|2.327980|4.185461|3.573667|4.320583|3.822499|6.229476|5.265199|5.304871|10.352999|0.185395|13.677093|7.782084|6.729021|7.837645|13.892634|36.858105| |1.461789|1.372768|1.396850|1.524264|1.653874|1.608354|1.842680|3.263625|2.770621|3.141079|2.698807|4.732910|3.221542|3.076177|4.993557|0.096366|4.802322|4.230668|4.765979|7.025578|10.915492|7.078714|448.794386| |4.619983|5.311450|8.202968|14.316873|7.906811|5.209154|6.637953|12.826251|6.178467|5.132245|3.095188|5.209287|2.656757|2.553418|2.991693|0.057302|2.076541|2.280317|2.123722|1.861216|1.748948|1.824184|12.191633|73.516695| |17.739482|8.855936|5.635650|4.924259|5.612871|8.950819|4.096111|5.916418|5.327428|4.155240|2.793386|5.347105|2.299609|2.091406|2.496213|0.047252|1.813529|2.054087|2.025942|1.778971|1.617658|1.625273|11.415299|6.516777|0.500000| |8.888319|17.714699|8.991100|5.646564|4.939853|5.672128|3.568357|5.574468|4.259356|3.480355|2.313150|4.260645|1.977219|1.842989|2.230715|0.042753|1.608810|1.783132|1.748708|1.562377|1.442845|1.456633|10.313318|7.627822|0.213652|0.500000| |5.619391|8.896544|17.744320|8.970496|5.640622|4.965257|4.132837|6.946926|4.503661|3.743367|2.410067|4.267598|2.087494|1.981363|2.387062|0.045967|1.695745|1.859377|1.788658|1.596438|1.491525|1.525697|10.614912|13.490932|0.123620|0.214783|0.500000| |9.021736|5.678664|4.964638|5.626368|8.875907|17.732433|6.955015|8.611341|10.166699|6.689323|4.252628|8.203626|3.212432|2.838500|3.241759|0.060142|2.329774|2.720372|2.611536|2.203637|1.983357|2.018894|13.558754|7.454251|0.217377|0.124739|0.107763|0.500000| |4.823876|3.867838|3.852121|4.775713|7.172366|7.161835|9.241446|10.926032|26.037606|12.988320|7.966257|15.623998|4.947068|4.025912|4.342281|0.077603|3.130610|3.879218|3.605966|2.864590|2.525331|2.595061|16.553568|7.186355|0.119309|0.089353|0.089126|0.248315|0.500000| |3.150852|2.869551|3.118308|3.997185|4.928523|4.052061|7.964236|15.685976|13.063800|26.003688|9.265757|11.002697|7.256776|6.887205|6.389886|0.112515|4.086541|4.768066|3.818802|3.048630|2.855791|3.161846|18.217513|7.148176|0.077978|0.068611|0.077070|0.117081|0.190292|0.500000| |2.279913|2.105015|2.227651|2.645930|3.033310|2.726940|3.956846|7.600319|6.212976|9.160156|6.447359|8.227789|8.654777|17.793737|12.280597|0.214169|5.885861|5.768134|4.078596|3.379993|3.419739|4.186334|21.242481|4.789555|0.058835|0.052274|0.056930|0.080145|0.110446|0.212184|0.500000| |2.290060|2.059663|2.067336|2.314519|2.670383|2.639004|3.064054|5.085314|5.057714|5.819992|6.107167|12.815268|6.450038|4.550904|5.911425|0.099075|5.627791|8.865593|17.764801|8.935917|5.627598|4.880441|31.575164|3.939062|0.061478|0.052115|0.052488|0.079913|0.112114|0.106284|0.102909|0.500000| |1.772854|1.636008|1.645928|1.800524|1.995362|1.969447|2.220196|3.810764|3.441920|3.862726|3.537614|6.661625|4.030915|3.406540|5.013780|0.089625|4.992948|5.654649|8.944668|17.754401|8.899668|5.626667|54.162589|3.124121|0.048064|0.042243|0.042698|0.058263|0.073687|0.074673|0.079478|0.214468|0.500000| |1.566650|1.471940|1.519130|1.691778|1.845852|1.755636|2.126942|3.865342|3.207714|3.827254|3.248049|5.279104|4.293253|4.615538|9.109991|0.187765|8.796826|5.560241|4.879029|5.593239|8.917043|17.746067|53.836879|3.038428|0.041800|0.037872|0.039847|0.051177|0.064165|0.078958|0.106768|0.106327|0.123907|0.500000| |4.166666|4.450943|6.082350|10.117210|7.778694|4.971859|8.023988|18.604018|7.023979|5.955210|3.459364|5.648556|2.967743|2.881689|3.322366|0.063480|2.273879|2.494835|2.281600|1.983290|1.871055|1.972396|12.915038|35.402793|0.093951|0.101456|0.153473|0.116168|0.121509|0.134868|0.085599|0.065602|0.051512|0.051264|0.500000| 1458.665099 -7108.084541 2512.760660 -159.761044 -3296.419826 1836.109962 -1460.309864 2.001128 4062000000000000 439AED87690A41FB 4324466BFAC273F0 418AF7DD80000005 37D16C2614EA0800 42FE83DBFC6B95C1