Version2.5 2022-11-16T10:19:20Z 10.1021/ja902302h Gaussian16 RevisionB.01 SBUNGAY 08-Nov-2022 #N HF/6-31G(d) OPT=(MaxStep=1) FREQ IOp(6/10=2,6/11=2,6/12=2) GDB_13 Smiles: CC1=C2C(C#N)C3CC3C2=NN1 RHF 6-31G(d) (6D,7F) CC1=C2C(C#N)C3CC3C2=NN1 C1[X(C9H9N3)] 57 C1 198 CC1=C2C(C#N)C3CC3C2=NN1 N#CC1C2CC2c2c1c(C)[nH]n2 Cc1[nH]nc2C3CC3C(C#N)c12 InChIKey=DZBAKBGIKTZMDC-UHFFFAOYSA-N InChI=1S/C9H9N3/c1-4-8-7(3-10)5-2-6(5)9(8)12-11-4/h5-7H,2H2,1H3,(H,11,12) InChI=1/C9H9N3/c1-4-8-7(3-10)5-2-6(5)9(8)12-11-4/h5-7H,2H2,1H3,(H,11,12)/f/h11H CC1=C2C(C#N)C3CC3C2=NN1 C01[X(C9H9N3)] 57 C1 198 CC1=C2C(C#N)C3CC3C2=NN1 NC[C@H]1[C@H]2C[C@H]2[C@@H]2[C@@H]1[C@@H](C)NN2 C[C@H]1NN[C@@H]2[C@@H]3C[C@@H]3[C@H](CN)[C@@H]12 InChIKey=PFQIOLYRXQXIBL-LTUMISQWSA-N InChI=1S/C9H17N3/c1-4-8-7(3-10)5-2-6(5)9(8)12-11-4/h4-9,11-12H,2-3,10H2,1H3/t4-,5+,6-,7+,8-,9-/m1/s1 InChI=1/C9H17N3/c1-4-8-7(3-10)5-2-6(5)9(8)12-11-4/h4-9,11-12H,2-3,10H2,1H3/t4-,5+,6-,7+,8-,9-/m1/s1 5.088064905593D+02 -2.513463723789D+03 662.6342485513 -509.3343598 1-A 1804.5681 42 156 198 |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| -15.63953 -15.58485 -15.56458 -11.29476 -11.29300 -11.26714 -11.25708 -11.25586 -11.25055 -11.24924 -11.24078 -11.22446 -1.38808 -1.22626 -1.20083 -1.12336 -1.08065 -1.02596 -0.96931 -0.88570 -0.82559 -0.80135 -0.76438 -0.70859 -0.68990 -0.67108 -0.63260 -0.62881 -0.61538 -0.57813 -0.57700 -0.56869 -0.54742 -0.54210 -0.52118 -0.46875 -0.46195 -0.45274 -0.44272 -0.42892 -0.34825 -0.34247 |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|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| 0.16079 0.20476 0.20827 0.22630 0.23216 0.23846 0.25092 0.28066 0.28582 0.30307 0.30931 0.31791 0.31983 0.34841 0.35757 0.38562 0.39711 0.41114 0.43974 0.46470 0.47107 0.49532 0.51489 0.54103 0.56809 0.60085 0.67767 0.69967 0.71715 0.73764 0.75648 0.76889 0.77834 0.81475 0.82515 0.82777 0.83246 0.84534 0.85707 0.86499 0.88685 0.89681 0.90301 0.91172 0.92634 0.94660 0.97215 0.97973 1.00082 1.03584 1.03877 1.05938 1.07237 1.10108 1.10598 1.11997 1.13038 1.13210 1.14501 1.14929 1.15410 1.17014 1.17736 1.19055 1.21030 1.22450 1.22952 1.23351 1.26084 1.32637 1.35581 1.37092 1.40460 1.46051 1.50885 1.54680 1.58131 1.59814 1.61834 1.65605 1.65729 1.69831 1.71281 1.74795 1.77847 1.79747 1.82666 1.83045 1.84378 1.91962 1.93629 1.96419 2.02170 2.04867 2.06392 2.11666 2.12808 2.15443 2.17063 2.19019 2.21841 2.22919 2.25529 2.27798 2.30571 2.31672 2.34712 2.35980 2.36768 2.41284 2.42010 2.45579 2.50202 2.51270 2.51828 2.58358 2.59901 2.62991 2.66199 2.66627 2.71451 2.71995 2.77742 2.78526 2.82446 2.83838 2.87669 2.92275 2.92972 2.98909 3.00970 3.01689 3.07002 3.08658 3.11811 3.15741 3.16481 3.20758 3.26187 3.32200 3.47526 3.55074 3.61558 3.68226 4.29309 4.50718 4.55385 4.60610 4.64027 4.67140 4.79149 4.82827 4.90418 5.00526 5.08359 5.26883

13.69429 2.2450 -1.1583 2.0960 3.2825 |XX|YY|ZZ|XY|XZ|YZ| -59.0033 -83.4775 -69.5632 13.6366 -4.6519 3.7162

|XX|YY|ZZ|XY|XZ|YZ| 11.6780 -12.7962 1.1182 13.6366 -4.6519 3.7162

|XXX|YYY|ZZZ|XYY|XXY|XXZ|XZZ|YZZ|YYZ|XYZ| 48.5776 -28.0418 1.7946 15.4837 -17.6253 0.0037 0.6228 -0.8457 17.1269 -6.7942

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13.0311 19.2903 10.3863 13.1054 10.4024 9.4739 17.9292 119.1115 0.4637 1.0809 4.2969 1.4516 1.5560 1.0578 2.2927 3.2196 1.1810 0.7798 1.4253 3.4135 2.1355 9.5802 1.4255 1.7684 5.3815 2.3472 11.2746 10.8914 6.9496 6.4175 10.4981 2.7844 4.0514 3.8973 1.1140 1.6863 3.6017 2.1875 0.1353 1.8366 6.9295 6.2798 11.3463 13.8337 4.7454 5.2452 5.1439 12.4766 21.7181 16.5888 14.1041 6.2260 8.6313 25.0476 4.3565 64.7758 157.6722 94.8435 93.9891 45.8930 97.2562 90.4847 142.1539 89.9398 101.0831 0.6995 0.7455 0.7154 0.6088 0.7500 0.6757 0.6717 0.7474 0.3753 0.1780 0.7484 0.3835 0.3649 0.1197 0.6873 0.4268 0.1601 0.7492 0.4321 0.6786 0.2940 0.7311 0.2661 0.6612 0.6369 0.5833 0.6211 0.4643 0.5229 0.7395 0.7084 0.0913 0.0741 0.4673 0.7268 0.6276 0.5267 0.5120 0.3378 0.7287 0.6452 0.5886 0.7377 0.6976 0.7500 0.1397 0.7293 0.2746 0.0477 0.2355 0.7449 0.7474 0.1651 0.4903 0.2279 0.4135 0.2935 0.8232 0.8542 0.8341 0.7568 0.8571 0.8065 0.8036 0.8555 0.5457 0.3023 0.8561 0.5544 0.5347 0.2138 0.8147 0.5983 0.2760 0.8566 0.6034 0.8085 0.4544 0.8447 0.4203 0.7960 0.7782 0.7368 0.7663 0.6342 0.6867 0.8502 0.8293 0.1673 0.1379 0.6370 0.8418 0.7712 0.6900 0.6773 0.5051 0.8431 0.7844 0.7410 0.8491 0.8219 0.8571 0.2451 0.8434 0.4308 0.0911 0.3812 0.8538 0.8554 0.2834 0.6580 0.3712 0.5850 0.4538

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 6 6 6 6 6 7 6 6 6 6 7 7 1 1 1 1 1 1 1 1 1 12.00000 12.00000 12.00000 12.00000 12.00000 14.00307 12.00000 12.00000 12.00000 12.00000 14.00307 14.00307 1.00783 1.00783 1.00783 1.00783 1.00783 1.00783 1.00783 1.00783 1.00783

1356.92616 1751.66307 2838.36083 0.97760 0.21048 -0.00205 -0.21045 0.97756 0.00956 0.00401 -0.00892 0.99995 1 0.06383 0.04945 0.03052 1.33002 1.03030 0.63584 90.46 126.59 158.10 243.77 315.69 376.28 481.10 563.97 653.71 726.54 767.50 779.32 845.75 951.80 984.13 1035.93 1145.71 1193.36 1244.84 1288.69 1319.65 1468.04 1522.17 1560.01 1581.27 1631.03 1653.00 1681.78 1723.28 1732.99 1775.36 1812.08 1865.34 1878.56 1997.15 2014.56 2083.15 2115.55 2162.33 2243.58 2280.01 2324.68 2346.14 2362.25 2382.02 2474.43 2633.22 3752.46 4621.02 4645.37 4703.25 4757.64 4770.70 4843.11 4862.10 4891.87 5637.57 0.180638 0.190087 0.191031 0.145120 -509.153722 -509.144273 -509.143329 -509.189240 1.539862D-04 MUNgauss RevisionA2.1 retrievium 16-Nov-2022 GDB_13 Smiles: CC1=C2C(C#N)C3CC3C2=NN1 RHF 6-31G(d) (6D,10F) C1 159.079647 |X|Y|Z| 30.661713 26.952115 11.747135

21.332434 9 6 7 7 2

|36.858105| |12.724896|36.858105| |7.261745|13.975107|36.858105| |5.296910|6.990273|12.624692|36.858105| |4.951621|5.618101|7.595824|12.895525|36.858105| |4.359159|4.548605|5.426009|7.291388|16.776516|53.358707| |3.881272|5.093675|8.010601|12.308062|7.551436|7.352474|36.858105| |3.509401|4.583117|6.460587|7.269344|6.015216|6.580155|12.744530|36.858105| |3.831796|5.368114|7.967043|7.582469|5.225795|5.567772|12.556958|12.682501|36.858105| |5.170764|8.666953|13.567553|7.902630|5.362214|5.679071|8.052385|7.616042|12.835637|36.858105| |5.179013|8.411504|8.476017|5.326296|4.126294|4.668909|5.212498|5.310642|7.407417|14.723839|53.358707| |7.631297|14.114935|8.878318|5.213523|4.241016|4.869523|4.481414|4.344506|5.365810|9.202106|19.254727|53.358707| |17.547759|8.893428|5.904522|4.593234|4.165303|5.027419|3.486707|3.093200|3.459820|4.522768|6.291123|8.857663|0.500000| |17.562154|8.894811|5.636953|4.275030|4.184559|5.265483|3.351983|3.185601|3.394231|4.472904|6.455296|9.463928|0.301218|0.500000| |17.607594|8.949486|6.764932|5.689305|5.876388|7.238852|3.961157|3.518040|3.671810|4.643495|5.915169|7.716740|0.301244|0.301902|0.500000| |4.999928|6.019710|8.824176|17.551534|9.208808|8.367778|8.806758|5.421047|5.990384|6.166195|6.200511|6.230611|0.128929|0.110098|0.150905|0.500000| |3.305635|4.078637|5.743429|8.486288|6.174349|6.483152|17.730955|8.602148|8.413180|5.754589|5.662236|4.975179|0.085075|0.080046|0.094679|0.216904|0.500000| |2.929577|3.645019|4.753916|5.382962|4.789925|5.597732|8.673088|17.709760|8.604036|5.512245|5.797944|4.813648|0.073237|0.075107|0.081890|0.122272|0.213231|0.500000| |3.752124|4.864740|6.538664|6.781700|6.396103|7.279919|8.547292|17.709523|8.565988|7.151245|7.258474|6.210197|0.089066|0.096669|0.105139|0.137347|0.171247|0.292774|0.500000| |3.264699|4.345319|5.742360|5.549798|4.107252|4.580351|8.371904|8.486575|17.739380|8.515587|8.566929|6.198337|0.084536|0.081598|0.086313|0.135344|0.200749|0.208216|0.170750|0.500000| |6.825264|9.058410|6.114156|4.122094|3.536207|4.216049|3.635722|3.590815|4.267190|6.337686|12.828381|26.102057|0.172476|0.194036|0.139442|0.104087|0.085390|0.084229|0.105094|0.105570|0.500000| 508.806568 -2513.463293 902.548969 -69.860900 -1171.968656 662.634296 -509.334360 2.001037 40677FFFFFFFFFFF 41B485CE43FFFFFD 414F45CC98618614 40C5038000000001 C022000000000000 416372561FFFFFFE