Supplementary Material

Ethanediol

tG(+)g(-)

MP2/cc-pVDZ dipole moment = 2.5102 D

A A A A A

Frequencies --- 188.4051 293.7257 349.7607 459.2025 566.5716

A A A A A

Frequencies --- 951.0377 967.5573 1161.3847 1201.5868 1232.7267

A A A A A

Frequencies --- 1263.8973 1365.1187 1400.9439 1492.8566 1539.5776

A A A A A

Frequencies --- 1593.1251 1611.0457 1620.7177 3156.6286 3168.5886

A A A A

Frequencies --- 3206.2705 3249.9323 4128.0914 4161.8859

1\1\GINC-SK\SP\RCCSD(T)\Gen\C2H6O2\MG37501\12-Aug-1993\0\\# CCSD(T)/GE N SCF=DIRECT GUESS=READ GEOM=CHECKPOINT\\lowest isomer glycol\\0,1\C\C ,1,1.5185619762\O,2,1.4283607909,1,105.41875252\O,1,1.4156461979,2,110 .55897773,3,59.46819874,0\H,3,0.965740737,2,107.31957379,1,-165.525270 68,0\H,4,0.9699651315,1,103.54420634,2,-48.79428587,0\H,2,1.1080580773 ,1,110.64819487,4,-179.51263827,0\H,2,1.1068692536,1,108.97400196,4,-5 9.93911673,0\H,1,1.1021004121,2,110.18181777,3,178.33738092,0\H,1,1.10 93160361,2,108.58475575,3,-63.49753704,0\\Version=CrayYMP-Unicos-G92Re vD.2\HF=-228.9506851\MP2=-229.6133365\MP3=-229.6425076\MP4D=-229.65672 \MP4DQ=-229.6469564\MP4SDQ=-229.6513795\CCSD=-229.651602\CCSD(T)=-229. 6688477\RMSD=4.488e-10\PG=C01 [X(C2H6O2)]\\@

g(+)G(+)g(-)

MP2/cc-pVDZ dipole moment = 2.2999 D

A A A A A

Frequencies --- 189.6061 337.6640 349.3339 473.5657 575.9519

A A A A A

Frequencies --- 942.9481 962.5183 1142.1211 1174.9518 1229.7055

A A A A A

Frequencies --- 1293.3976 1335.8027 1479.8811 1490.0388 1521.8918

A A A A A

Frequencies --- 1571.8508 1607.0399 1617.6290 3128.4869 3176.2876

A A A A

Frequencies --- 3239.1984 3265.2233 4121.8314 4140.0096

1\1\GINC-SK\SP\RCCSD(T)\Gen\C2H6O2\MG37501\12-Aug-1993\0\\# CCSD(T)/GE N SCF=DIRECT GUESS=READ GEOM=CHECKPOINT\\lowest isomer glycol\\0,1\C\C ,1,1.5220330711\O,2,1.4296075249,1,109.76248388\O,1,1.4144622799,2,110 .28221086,3,54.90534518,0\H,3,0.9683762005,2,106.14934588,1,70.8075177 8,0\H,4,0.9708305457,1,103.59412016,2,-41.36142808,0\H,2,1.1073507946, 1,111.28436832,4,-180.44536246,0\H,2,1.1013933726,1,109.44924589,4,-60 .48147794,0\H,1,1.102934405,2,110.66302612,3,174.30537133,0\H,1,1.1132 01398,2,108.93548303,3,-67.92756687,0\\Version=CrayYMP-Unicos-G92RevD. 2\HF=-228.9496323\MP2=-229.6133934\MP3=-229.6424139\MP4D=-229.6566753\ MP4DQ=-229.6467883\MP4SDQ=-229.6514006\CCSD=-229.6515709\CCSD(T)=-229. 6690418\RMSD=2.682e-09\PG=C01 [X(C2H6O2)]\\@

g(-)G(+)g(-)

MP2/cc-pVDZ dipole moment = 0.0387 D

B A A A B

Frequencies --- 74.0823 163.1043 337.6267 450.0375 571.8866

B A A B A

Frequencies --- 942.0894 951.8157 1139.5954 1163.4335 1228.1455

B A B A B

Frequencies --- 1274.3532 1345.4767 1497.7010 1498.9540 1515.8033

A B A A B

Frequencies --- 1552.8527 1601.8466 1608.5649 3176.9273 3177.0555

A B B A

Frequencies --- 3244.8802 3248.9028 4154.4911 4156.8606

1\1\GINC-SK\SP\RCCSD(T)\Gen\C2H6O2\MG37501\12-Aug-1993\0\\# CCSD(T)/GE N SCF=DIRECT GUESS=READ GEOM=CHECKPOINT\\lowest isomer glycol\\0,1\C\C ,1,1.5233380485\O,2,1.4250820153,1,110.65781649\O,1,1.4250820153,2,110 .65781649,3,55.77268485,0\H,3,0.9668932782,2,104.95730777,1,-76.481476 77,0\H,4,0.9668932782,1,104.95730777,2,-76.48147677,0\H,2,1.1028892675 ,1,110.33122287,4,174.08140289,0\H,2,1.1072218453,1,109.46723791,4,-67 .098008,0\H,1,1.1072218453,2,109.46723791,3,-67.098008,0\H,1,1.1028892 675,2,110.33122287,3,174.08140289,0\\Version=CrayYMP-Unicos-G92RevD.2\ State=1-A\HF=-228.948292\MP2=-229.6108169\MP3=-229.640133\MP4D=-229.65 43673\MP4DQ=-229.6445591\MP4SDQ=-229.6491172\CCSD=-229.6493418\CCSD(T) =-229.6666321\RMSD=1.624e-09\PG=C02 [X(C2H6O2)]\\@

tTg(+)

MP2/cc-pVDZ dipole moment = 2.2337 D

A A A A A

Frequencies --- 154.2867 275.9467 303.3237 326.6289 515.9046

A A A A A

Frequencies --- 875.3448 1088.4591 1168.7864 1194.0057 1204.1091

A A A A A

Frequencies --- 1304.5827 1340.2754 1409.3703 1476.6268 1509.1938

A A A A A

Frequencies --- 1600.1756 1622.6955 1636.5081 3133.2562 3179.8743

A A A A

Frequencies --- 3194.1025 3270.8620 4148.9117 4162.5874

1\1\GINC-SK\SP\RCCSD(T)\Gen\C2H6O2\MG37501\13-Aug-1993\0\\# CCSD(T)/GE N SCF=DIRECT GUESS=READ GEOM=CHECKPOINT\\lowest isomer glycol\\0,1\C\C ,1,1.5228613721\O,2,1.4193831689,1,107.09357601\O,1,1.419472004,2,111. 83159657,3,-178.78733035,0\H,3,0.9655328762,2,106.92918686,1,176.84225 629,0\H,4,0.9668149136,1,106.27536138,2,-68.26887063,0\H,2,1.10753171, 1,108.67071469,4,-56.81679712,0\H,2,1.1114946226,1,109.03367034,4,60.0 1633659,0\H,1,1.1009860136,2,109.00865763,3,-61.00375277,0\H,1,1.10754 19417,2,108.9502887,3,55.99488035,0\\Version=CrayYMP-Unicos-G92RevD.2\ HF=-228.9471306\MP2=-229.6080555\MP3=-229.6377838\MP4D=-229.6519575\MP 4DQ=-229.6422591\MP4SDQ=-229.6465334\CCSD=-229.6468057\CCSD(T)=-229.66 38477\RMSD=1.246e-09\PG=C01 [X(C2H6O2)]\\@

g(+)Tg(-)

MP2/cc-pVDZ dipole moment = 0.0000 D

AU AU AG AU AG

Frequencies --- 160.4823 294.6564 323.0054 335.6735 514.6183

AU AG AG AU AG

Frequencies --- 857.8520 1105.2479 1169.3408 1194.3152 1206.8909

AU AG AU AG AU

Frequencies --- 1220.0300 1410.4893 1438.4754 1480.2681 1520.7114

AG AG AU AG AU

Frequencies --- 1573.0181 1616.2964 1627.5942 3173.1849 3177.0429

AG AU AU AG

Frequencies --- 3218.5163 3245.9229 4145.1343 4146.4129

1\1\GINC-SK\SP\RCCSD(T)\Gen\C2H6O2\MG37501\12-Aug-1993\0\\# CCSD(T)/GE N SCF=DIRECT GUESS=READ GEOM=CHECKPOINT\\lowest isomer glycol\\0,1\C\C ,1,1.5279761064\O,2,1.4190628093,1,112.19706548\O,1,1.4190628093,2,112 .19706548,3,180.,0\H,3,0.9669966902,2,106.20793023,1,66.86209405,0\H,4 ,0.9669966902,1,106.20793023,2,-66.86209405,0\H,2,1.1078185915,1,108.9 694991,4,-54.32447925,0\H,2,1.1040918638,1,109.39870002,4,62.6100975,0 \H,1,1.1040918638,2,109.39870002,3,-62.6100975,0\H,1,1.1078185915,2,10 8.9694991,3,54.32447925,0\\Version=CrayYMP-Unicos-G92RevD.2\State=1-AG \HF=-228.9470826\MP2=-229.6088868\MP3=-229.6384464\MP4D=-229.6526642\M P4DQ=-229.6428653\MP4SDQ=-229.6472799\CCSD=-229.6474882\CCSD(T)=-229.6 646976\RMSD=9.011e-10\PG=CI [X(C2H6O2)]\\@

g(+)G(+)g(+)

MP2/cc-pVDZ dipole moment = 1.2844 D

A B A A B

Frequencies --- 113.9509 170.7013 305.7803 334.7647 579.9445

A B A B A

Frequencies --- 946.8155 963.9364 1136.0475 1205.2222 1253.0278

B A A B B

Frequencies --- 1253.0995 1391.3620 1441.1502 1486.9776 1541.2186

A B A B A

Frequencies --- 1576.7651 1618.9781 1624.0124 3141.6456 3163.4240

A B B A

Frequencies --- 3203.7217 3227.2806 4140.0943 4140.8854

1\1\GINC-SK\SP\RCCSD(T)\Gen\C2H6O2\MG37501\13-Aug-1993\0\\# CCSD(T)/GE N SCF=DIRECT GUESS=READ GEOM=CHECKPOINT\\lowest isomer glycol\\0,1\C\C ,1,1.5249001646\O,2,1.4174132357,1,112.84774177\O,1,1.4174132357,2,112 .84774177,3,-46.04686624,0\H,3,0.9675835649,2,106.34070653,1,-40.97599 676,0\H,4,0.9675835649,1,106.34070653,2,-40.97599676,0\H,2,1.110009898 1,1,108.7628341,4,188.28761335,0\H,2,1.1052879698,1,109.68735031,4,71. 65544401,0\H,1,1.1052879698,2,109.68735031,3,71.65544401,0\H,1,1.11000 98981,2,108.7628341,3,188.28761335,0\\Version=CrayYMP-Unicos-G92RevD.2 \State=1-A\HF=-228.945668\MP2=-229.6081276\MP3=-229.6376058\MP4D=-229. 6518163\MP4DQ=-229.6420036\MP4SDQ=-229.6464378\CCSD=-229.6466222\CCSD( T)=-229.6638984\RMSD=1.491e-09\PG=C02 [X(C2H6O2)]\\@

tG(+)g(+)

MP2/cc-pVDZ dipole moment = 3.0537 D

A A A A A

Frequencies --- 146.2266 266.6978 291.4855 359.4103 553.3651

A A A A A

Frequencies --- 943.7270 977.3344 1136.5630 1199.3491 1242.8736

A A A A A

Frequencies --- 1286.5968 1361.4533 1418.6360 1489.4367 1539.5162

A A A A A

Frequencies --- 1600.4634 1606.7542 1621.5430 3117.9342 3148.5804

A A A A

Frequencies --- 3165.4129 3262.7633 4144.4620 4157.9701

1\1\GINC-SK\SP\RCCSD(T)\Gen\C2H6O2\MG37501\13-Aug-1993\0\\# CCSD(T)/GE N SCF=DIRECT GUESS=READ GEOM=CHECKPOINT\\lowest isomer glycol\\0,1\C\C ,1,1.5195656832\O,2,1.4163432681,1,108.42240279\O,1,1.4156972334,2,113 .6363749,3,62.6351169,0\H,3,0.9657873411,2,106.74958965,1,-178.0761642 4,0\H,4,0.9669273989,1,106.31280795,2,57.24758106,0\H,2,1.110336162,1, 108.35303994,4,-175.27697651,0\H,2,1.1125900093,1,108.87614853,4,-59.1 5949215,0\H,1,1.1104551421,2,108.27191146,3,188.00189257,0\H,1,1.10178 27854,2,108.6292743,3,-55.14726912,0\\Version=CrayYMP-Unicos-G92RevD.2 \HF=-228.944642\MP2=-229.6064389\MP3=-229.6360286\MP4D=-229.6502198\MP 4DQ=-229.6404894\MP4SDQ=-229.6447943\CCSD=-229.6450133\CCSD(T)=-229.66 21513\RMSD=6.591e-10\PG=C01 [X(C2H6O2)]\\@

g(+)Tg(+)

MP2/cc-pVDZ dipole moment = 2.3411 D

A A B B A

Frequencies --- 163.5500 299.3584 303.3705 345.0832 515.0487

A A B B A

Frequencies --- 858.8306 1116.9977 1141.2216 1196.2913 1208.8449

A B B B A

Frequencies --- 1237.5660 1399.4187 1442.2491 1499.2202 1503.5294

A A B B A

Frequencies --- 1572.5556 1616.0281 1627.0338 3128.4916 3140.9552

B A B A

Frequencies --- 3255.3851 3273.5619 4144.9574 4145.9870

1\1\GINC-SK\SP\RCCSD(T)\Gen\C2H6O2\MG37501\13-Aug-1993\0\\# CCSD(T)/GE N SCF=DIRECT GUESS=READ GEOM=CHECKPOINT\\lowest isomer glycol\\0,1\C\C ,1,1.5276798599\O,2,1.4181760974,1,112.29572296\O,1,1.4181760974,2,112 .29572296,3,175.47982206,0\H,3,0.967099787,2,106.37248021,1,63.7910632 2,0\H,4,0.967099787,1,106.37248021,2,63.79106322,0\H,2,1.1010346379,1, 109.01388408,4,57.34297193,0\H,2,1.1117997863,1,109.32563666,4,-59.561 6635,0\H,1,1.1117997863,2,109.32563666,3,-59.5616635,0\H,1,1.101034637 9,2,109.01388408,3,57.34297193,0\\Version=CrayYMP-Unicos-G92RevD.2\Sta te=1-A\HF=-228.9465212\MP2=-229.6084721\MP3=-229.6380241\MP4D=-229.652 2488\MP4DQ=-229.6424338\MP4SDQ=-229.6468671\CCSD=-229.6470621\CCSD(T)= -229.6643023\RMSD=9.636e-11\PG=C02 [X(C2H6O2)]\\@

tTt

MP2/cc-pVDZ dipole moment = 0.0000 D

AU BG AU BU AG

Frequencies --- 149.7576 273.1393 275.8703 315.8653 516.9280

AU AG BU AG BG

Frequencies --- 895.5270 1065.8855 1192.9069 1202.2131 1255.6653

BU AU AG BG BU

Frequencies --- 1286.0942 1328.1266 1401.2229 1407.4690 1526.5481

AG AG BU BU AG

Frequencies --- 1620.8109 1638.0339 1642.1866 3165.0487 3166.3434

BG AU AG BU

Frequencies --- 3191.0534 3221.5484 4163.7493 4164.0029

1\1\GINC-SK\SP\RCCSD(T)\Gen\C2H6O2\MG37501\12-Aug-1993\0\\# CCSD(T)/GE N SCF=DIRECT GUESS=READ GEOM=CHECKPOINT\\lowest isomer glycol\\0,1\C\C ,1,1.5172480199\O,2,1.4203249919,1,106.82906266\O,1,1.4203249919,2,106 .82906266,3,180.,0\H,3,0.9652713541,2,106.72594969,1,180.,0\H,4,0.9652 713541,1,106.72594969,2,180.,0\H,2,1.107614124,1,108.65395091,4,58.481 31876,0\H,2,1.107614124,1,108.65395091,4,-58.48131876,0\H,1,1.10761412 4,2,108.65395091,3,58.48131876,0\H,1,1.107614124,2,108.65395091,3,-58. 48131876,0\\Version=CrayYMP-Unicos-G92RevD.2\State=1-AG\HF=-228.947680 2\MP2=-229.6078204\MP3=-229.6376567\MP4D=-229.6517939\MP4DQ=-229.64219 09\MP4SDQ=-229.6463175\CCSD=-229.6466561\CCSD(T)=-229.6635321\RMSD=1.2 04e-09\PG=C02H [SGH(C2H2O2),X(H4)]\\@

tG(+)t

MP2/cc-pVDZ dipole moment = 1.4410 D

A A B A B

Frequencies --- 171.6972 222.3460 230.7254 361.9360 535.3610

A B A B A

Frequencies --- 953.9245 995.4369 1148.3104 1192.0755 1231.8091

B A B A B

Frequencies --- 1317.7653 1356.1477 1409.0900 1428.9026 1549.6453

B A A B A

Frequencies --- 1615.1605 1616.7753 1621.7060 3135.4272 3159.0575

A B B A

Frequencies --- 3188.8714 3205.7668 4162.0176 4162.5855

1\1\GINC-SK\SP\RCCSD(T)\Gen\C2H6O2\MG37501\13-Aug-1993\0\\# CCSD(T)/GE N SCF=DIRECT GUESS=READ GEOM=CHECKPOINT\\lowest isomer glycol\\0,1\C\C ,1,1.514030671\O,2,1.4188570761,1,108.14240681\O,1,1.4188570761,2,108. 14240681,3,72.5222739,0\H,3,0.9654742937,2,106.71389913,1,191.01302836 ,0\H,4,0.9654742937,1,106.71389913,2,191.01302836,0\H,2,1.1097982243,1 ,108.64714605,4,194.00006847,0\H,2,1.1077373255,1,108.00806382,4,-48.9 7416686,0\H,1,1.1077373255,2,108.00806382,3,-48.97416686,0\H,1,1.10979 82243,2,108.64714605,3,194.00006847,0\\Version=CrayYMP-Unicos-G92RevD. 2\State=1-A\HF=-228.9452087\MP2=-229.6064192\MP3=-229.6360524\MP4D=-22 9.6502175\MP4DQ=-229.6405649\MP4SDQ=-229.6447556\CCSD=-229.6450396\CCS D(T)=-229.6620417\RMSD=7.662e-10\PG=C02 [X(C2H6O2)]\\@