Version2.6 2023-02-14T14:22:52Z 10.1021/ja902302h Gaussian16 RevisionB.01 DOC1ROB 31-Jan-2023 #N HF/6-31G(d) OPT=(MaxStep=1) FREQ IOp(6/10=2,6/11=2,6/12=2) GDB_13 Smiles: CCC1=NN=CC(=C)C(=C1)C#N RHF 6-31G(d) (6D,7F) CCC1=NN=CC(=C)C(=C1)C#N C1[X(C9H9N3)] 57 C1 198 CCC1=NN=CC(=C)C(=C1)C#N CCC1=NN=CC(=C)C(=C1)C#N CCC1=NN=CC(=C)C(=C1)C#N InChIKey=SCYGFTVTLCWAOR-UHFFFAOYSA-N InChI=1S/C9H9N3/c1-3-9-4-8(5-10)7(2)6-11-12-9/h4,6H,2-3H2,1H3 InChI=1/C9H9N3/c1-3-9-4-8(5-10)7(2)6-11-12-9/h4,6H,2-3H2,1H3 CCC1=NN=CC(=C)C(=C1)C#N C01[X(C9H9N3)] 57 C1 198 CCC1=NN=CC(=C)C(=C1)C#N CC[C@@H]1NNC[C@H]([C@H](C1)CN)C CC[C@H]1C[C@H](CN)[C@H](C)CNN1 InChIKey=BPUAPLZDZVFZGT-HLTSFMKQSA-N InChI=1S/C9H21N3/c1-3-9-4-8(5-10)7(2)6-11-12-9/h7-9,11-12H,3-6,10H2,1-2H3/t7-,8-,9+/m1/s1 InChI=1/C9H21N3/c1-3-9-4-8(5-10)7(2)6-11-12-9/h7-9,11-12H,3-6,10H2,1-2H3/t7-,8-,9+/m1/s1 5.086800314160D+02 -2.443018843060D+03 627.8558952542 -509.2941583 1-A 2174.5460 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| -15.61181 -15.60753 -15.59038 -11.31699 -11.30822 -11.29917 -11.29055 -11.29047 -11.28444 -11.26624 -11.24646 -11.21719 -1.34818 -1.24671 -1.18009 -1.16207 -1.06140 -1.04724 -0.95232 -0.89785 -0.86347 -0.81529 -0.76036 -0.72460 -0.67034 -0.66300 -0.64304 -0.63409 -0.62790 -0.58599 -0.57066 -0.55823 -0.52832 -0.52757 -0.52002 -0.50965 -0.48596 -0.45862 -0.44228 -0.41095 -0.40037 -0.35463 |A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A|A| 0.05625 0.09623 0.16984 0.20971 0.22601 0.23815 0.25406 0.26090 0.28510 0.29268 0.30045 0.30698 0.31817 0.32688 0.34395 0.37429 0.38910 0.40729 0.41909 0.45264 0.47247 0.49803 0.51671 0.55761 0.58620 0.60801 0.64937 0.69725 0.70830 0.73313 0.73591 0.74436 0.75416 0.77972 0.78687 0.79948 0.81248 0.82551 0.83342 0.85566 0.87686 0.88185 0.89385 0.90895 0.92322 0.93191 0.95375 0.96672 0.98917 1.00779 1.02740 1.04564 1.05938 1.07639 1.08723 1.09958 1.11661 1.12026 1.12829 1.13830 1.14972 1.16782 1.17391 1.19601 1.20437 1.20949 1.22170 1.23400 1.24711 1.27857 1.28677 1.32599 1.35456 1.37801 1.39987 1.43918 1.47541 1.50964 1.54693 1.59376 1.61430 1.64196 1.69444 1.71602 1.73446 1.75563 1.78306 1.82844 1.83141 1.86465 1.88265 1.89955 1.93644 1.96022 1.97364 1.98502 2.06089 2.06635 2.08473 2.10626 2.12858 2.18239 2.19538 2.23727 2.26692 2.27310 2.30289 2.31212 2.32237 2.33279 2.37807 2.38960 2.41940 2.43160 2.48099 2.50620 2.54337 2.59109 2.62349 2.65207 2.65740 2.66655 2.70141 2.72613 2.74366 2.75965 2.79355 2.86988 2.88872 2.91665 2.96411 2.97951 3.04508 3.09448 3.13117 3.16125 3.17807 3.21511 3.29685 3.40196 3.46497 3.52737 3.67688 3.76031 4.30121 4.45447 4.48609 4.52509 4.55596 4.59523 4.62673 4.66369 4.77027 4.90394 4.94387 5.13959

11.18052 0.7431 -0.0744 1.4524 1.6331 |XX|YY|ZZ|XY|XZ|YZ| -81.4093 -73.0387 -69.9298 -18.2534 -2.1417 3.0036

|XX|YY|ZZ|XY|XZ|YZ| -6.6167 1.7539 4.8628 -18.2534 -2.1417 3.0036

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40.8616 35.5661 28.5518 3.8283 14.9845 2.3355 3.7546 5.4092 3.2806 4.9795 3.9967 4.5378 2.1959 0.4442 4.3318 1.4617 3.9329 4.6007 3.1064 1.1335 3.4298 3.2658 2.6458 2.5907 8.2801 9.0911 9.5257 0.9029 3.1366 1.5386 6.4822 4.2932 7.9239 8.1485 6.1707 5.6199 11.3389 2.5506 2.3765 5.4728 10.2809 7.4573 16.7424 3.4941 8.7130 5.1259 48.6015 23.6598 22.3858 6.5133 88.4479 94.5359 56.3405 209.9469 228.8195 98.0796 83.9750 160.0436 86.3383 39.4043 44.9751 158.0375 74.0713 71.0883 0.6660 0.6936 0.6966 0.7489 0.7256 0.7434 0.6684 0.7495 0.7367 0.3021 0.7446 0.2156 0.3586 0.5696 0.6053 0.3342 0.6247 0.6727 0.0533 0.4792 0.2465 0.2908 0.5460 0.4797 0.6617 0.6267 0.5004 0.6294 0.4137 0.2890 0.4572 0.5715 0.5873 0.7487 0.7483 0.4986 0.7496 0.5494 0.5382 0.5449 0.7354 0.7492 0.5719 0.3516 0.1089 0.6794 0.1624 0.3136 0.1644 0.7428 0.0597 0.7468 0.7364 0.3854 0.1633 0.3192 0.7406 0.7995 0.8191 0.8212 0.8564 0.8410 0.8528 0.8012 0.8568 0.8484 0.4640 0.8536 0.3547 0.5279 0.7258 0.7541 0.5010 0.7690 0.8044 0.1012 0.6479 0.3955 0.4506 0.7063 0.6484 0.7964 0.7705 0.6670 0.7725 0.5853 0.4484 0.6275 0.7273 0.7400 0.8563 0.8560 0.6654 0.8569 0.7092 0.6998 0.7054 0.8475 0.8566 0.7276 0.5203 0.1964 0.8091 0.2794 0.4775 0.2824 0.8524 0.1126 0.8550 0.8482 0.5563 0.2807 0.4840 0.8510

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

1155.43749 2660.02018 3418.46400 0.99846 -0.05551 0.00145 0.05550 0.99842 0.00887 -0.00194 -0.00878 0.99996 1 0.07496 0.03256 0.02534 1.56195 0.67847 0.52794 85.05 101.02 183.80 217.75 285.37 321.12 394.08 446.93 479.17 541.85 602.05 663.48 702.81 813.95 931.20 939.18 967.79 1062.48 1157.72 1170.96 1248.98 1267.47 1418.38 1469.37 1482.73 1506.21 1531.98 1594.03 1632.87 1689.31 1744.96 1765.47 1842.70 2019.22 2038.54 2168.32 2184.00 2207.91 2260.97 2283.21 2333.73 2355.88 2364.49 2617.44 2667.25 2719.00 2760.52 3748.94 4583.66 4622.73 4634.91 4727.85 4758.97 4812.24 4818.51 4860.05 4934.83 0.176938 0.187407 0.188351 0.140304 -509.117220 -509.106751 -509.105807 -509.153854 1.611504D-04 MUNgauss RevisionA2.1 retrievium 14-Feb-2023 GDB_13 Smiles: CCC1=NN=CC(=C)C(=C1)C#N RHF 6-31G(d) (6D,10F) C1 159.079647 |X|Y|Z| 24.088244 37.719077 13.098328

22.831127 7 6 7 5 2

|36.858105| |12.499375|36.858105| |7.431982|12.570902|36.858105| |6.866978|7.971931|15.101333|53.358707| |4.620563|5.158309|8.191036|18.921111|53.358707| |3.784717|4.358451|6.587169|11.230386|20.663849|36.858105| |3.618596|4.409845|6.454541|8.848269|10.492072|12.782783|36.858105| |3.063675|3.564498|4.639174|6.408831|7.279298|7.716922|14.422155|36.858105| |3.851498|5.175717|7.699837|8.496545|8.547197|7.681462|12.821503|7.683790|36.858105| |4.904114|7.581383|12.874115|10.541269|8.831061|6.461001|7.707362|5.272253|14.323111|36.858105| |3.078205|3.968420|5.029504|5.784513|5.907831|5.186296|7.578824|6.323769|13.164111|7.943758|36.858105| |2.638833|3.293260|3.907855|4.619172|4.724675|4.044245|5.399938|5.051095|7.375050|5.536123|16.768924|53.358707| |17.554852|8.870779|5.468860|6.743781|4.986038|3.130184|3.065296|2.672863|3.298351|4.091047|2.754763|3.289511|0.500000| |17.602118|8.799347|6.716246|9.468752|6.563976|3.781068|3.431318|2.884258|3.588210|4.502810|2.884059|3.383119|0.300635|0.500000| |17.593693|8.797225|6.712199|9.386120|6.434284|3.917403|3.745631|3.241631|3.780442|4.541114|3.002585|3.501612|0.300875|0.302745|0.500000| |8.840493|17.491595|9.001457|8.421931|6.077306|3.836083|3.859477|3.149644|4.700946|6.943247|3.814982|4.406800|0.214109|0.210508|0.172900|0.500000| |8.833075|17.506867|8.976634|8.347428|5.965598|3.972378|4.315520|3.625404|5.153459|7.083038|4.100305|4.677242|0.214346|0.172884|0.209927|0.305130|0.500000| |3.168469|3.518910|4.849099|7.975869|13.141371|17.674888|8.687178|6.769106|5.791843|4.878523|4.482366|5.019357|0.074732|0.089422|0.090965|0.088736|0.090131|0.500000| |2.830580|3.151857|3.979989|5.804805|6.820700|7.047495|9.117725|17.720785|5.509782|4.220478|4.708822|5.447037|0.068919|0.075088|0.084473|0.077590|0.087905|0.192745|0.500000| |2.835759|3.325213|4.104052|5.385713|5.756560|5.510691|9.076698|17.723561|6.950950|4.843687|6.746418|7.759771|0.070223|0.073212|0.082672|0.082781|0.097081|0.137950|0.288771|0.500000| |4.552326|7.091891|8.712945|7.790430|6.638713|4.795039|5.532032|4.228193|9.156712|17.716279|7.362098|7.632294|0.110975|0.116003|0.112752|0.209325|0.192155|0.108525|0.096742|0.113598|0.500000| 508.680310 -2443.019682 866.898608 -69.709334 -1137.150098 627.855940 -509.294158 2.001207 400FFFFFFFFFFFEB 41B456247B000000 414EFD2B66186186 406D5FFFFFFFFFFF 3FF0000000000000 41134CA000000000