Supporting Information
Ring Opening of Monocyclic Dimethyl Cyclopropene via Metathesis by Tungsten Catalyst- A Computational Study
Jay Singh Meena, Pompozhi Protasis Thankachan*
Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee-247667, India
E-mail: , * Phone: +91-1332-6228
Table S1 Selected geometrical parameters of the tungsten catalyst model W(NH)(CH2)(OCH3)2(1) and 3,3-dimethyl cyclopropene (2)
Parameter / 1 / Parameter / 2W-C1 / 1.912 / C4-C6 / 1.323
W-O1 / 1.889 / C4-C5 / 1.544
W-O2 / 1.889 / C6-C5 / 1.544
W-N1 / 1.751 / C4-H10 / 1.079
N-W-C1 / 102.0 / C6-H11 / 1.079
W-C1-H9 / 128.737 / C5-C4-C6 / 64.638
W-C1-H2 / 116.773 / C4-C6-C5 / 64.638
W-N1-H1 / 173.375 / C4-C5-C6 / 50.725
C1-W-O1 / 107.113 / C7-C5-C8 / 113.239
C1-W-O2 / 107.113
W-O1-C3 / 149.533
W-O2-C2 / 149.533
O1-W-O2 / 108.137
a Bond lengths are given in Å and angles in degrees
Table S2Optimized structural parameters (bond lengths in Ǻand angles in degree) for the transition structures (TS) ,Trigonal bipyramidal (TBP), Square pyramidal (SP) and ring opening metathesis product (ROP) of 3,3-Dimethyl Cyclopropene with W(NH)(CH2)(OCH3)2(CNO face)
Parameter / W(NH)(CH2)(OCH3)2 + 3,3 DMCPSYN / ANTI
SCTS / STBP / SSP / SRTS / SROP / ACTS / ATBP / ASP / ARTS / AROP
W-N1 / 1.769 / 1.778 / 1.747 / 1.771 / 1.753 / 1.771 / 1.778 / 1.749 / 1.767 / 1.751
W-O1 / 1.923 / 1.942 / 1.893 / 1.915 / 1.895 / 1.935 / 1.956 / 1.889 / 1.935 / 1.893
W-O2 / 1.920 / 1.950 / 1.892 / 1.927 / 1.894 / 1.921 / 1.946 / 1.890 / 1.938 / 1.891
W-C1 / 1.922 / 2.170 / 2.207 / 2.686 / - / 1.927 / 2.180 / 2.211 / 2.814 / -
W-C6 / 2.864 / 2.048 / 2.144 / 1.958 / 1.912 / 2.697 / 2.042 / 2.152 / 1.956 / 1.927
C1-C4 / 3.184 / 1.520 / 1.523 / 1.387 / 1.349 / 2.998 / 1.514 / 1.524 / 1.378 / 1.350
C4-C6 / 1.336 / 1.677 / 1.579 / 2.155 / - / 1.345 / 1.692 / 1.551 / 2.179 / -
N-W-O1 / 102.1 / 93.3 / 113.1 / 104.8 / 115.6 / 98.96 / 92.7 / 113.6 / 99.3 / 115.4
N-W-O2 / 140.0 / 169.9 / 112.1 / 134.8 / 115.2 / 154.3 / 163.2 / 113.6 / 133.8 / 115.3
N-W-C1 / 102.3 / 91.1 / 103.0 / 79.5 / - / 102.1 / 96.8 / 98.8 / 103.5 / -
O1-W-O2 / 88.0 / 81.5 / 99.0 / 87.0 / 108.2 / 85.18 / 79.8 / 100.1 / 85.3 / 108.2
C1-W-O1 / 103.1 / 143.3 / 138.5 / 170.2 / - / 104.6 / 147.5 / 140.4 / 154.7 / -
C1-W-O2 / 113.0 / 88.0 / 85.0 / 83.9 / - / 110.1 / 82.4 / 86.1 / 71.0 / -
C6-W-O1 / 152.5 / 134.6 / 84.8 / 107.7 / 106.9 / 151.6 / 129.5 / 86.2 / 106.7 / 108.6
C6-W-O2 / 74.0 / 90.6 / 137.7 / 113.8 / 106.4 / 77.0 / 98.8 / 139.2 / 118.7 / 107.5
W-O1-C2 / 131.1 / 133.6 / 154.8 / 131.3 / 148.8 / 129.3 / 131.6 / 152.0 / 127.5 / 152.0
W-O2-C3 / 142.0 / 142.3 / 156.2 / 139.9 / 147.6 / 142.2 / 141.1 / 155.3 / 134.4 / 150.3
C1-W-C6 / 102.9 / 80.1 / 66.4 / 80.2 / - / 102.2 / 79.9 / 65.6 / 77.4 / -
W-C1-C4 / 64.5 / 80.4 / 95.5 / 76.1 / - / 66.3 / 80.8 / 96.1 / 77.2 / -
C1-C4-C6 / 106.6 / 116.2 / 100.4 / 116.8 / - / 107.2 / 115.6 / 100.5 / 116.8 / -
W-C6-C4 / 79.3 / 80.9 / 96.3 / 82.3 / - / 81.9 / 81.3 / 97.7 / 86.8 / -
N-W-C6 / 80.5 / 99.1 / 104.6 / 104.3 / 103.7 / 84.2 / 97.5 / 100.0 / 103.7 / 101.0
1
Table S3 Optimized structural parameters (bond lengths in Ǻ and angles in degree) for the transition structures (TS), Trigonal bipyramidal (TBP), of the 3, 3 DimethylCyclopropene with of W(NH)(CH2)(OCH3)2catalyst (1) On the COO Face
Parameter / COO_TS / Coo_TBPW-N1 / 1.789 / 1.793
W-C1 / 1.951 / 2.15
W-C6 / 2.586 / 2.13
C1-C4 / 2.806 / 1.52
C4-C6 / 1.362 / 1.670
N-W-O1 / 94.87 / 91.76
N-W-O2 / 95.79 / 93.47
N-W-C1 / 116.6 / 125.4
O1-W-O2 / 153.54 / 169.8
C1-W-O1 / 98.11 / 93.18
C1-W-O2 / 98.61 / 90.90
C6-W-O1 / 75.09 / 82.20
C6-W-O2 / 82.01 / 89.48
C1-W-C6 / 99.54 / 78.59
W-C1-C4 / 67.95 / 82.39
C1-C4-C6 / 108.59 / 116.1
W-C6-C4 / 82.06 / 79.8
Table S4 Optimized Cartesian coordinates (in Å) with total electronic energy (in hartree) of the key species involved in the reaction of 3,3-dimethyle cyclopropene with W(NH)(CH2)(OCH3)2 at B3LYP/LANL2DZ level of theory.
W(NH)(CH2)(OCH3)2
7 -0.642791000 1.852762000 0.000000000
1 -0.836220000 2.846875000 0.000000000
8 0.845509000 -0.374552000 1.529529000
8 0.845509000 -0.374552000 -1.529529000
6 -1.773466000 -0.762749000 0.000000000
1 -1.717811000 -1.862947000 0.000000000
6 0.845509000 -0.880026000 -2.875090000
1 0.867712000 -0.042659000 -3.584306000
1 1.740424000 -1.497849000 -3.016653000
1 -0.054841000 -1.485146000 -3.052121000
6 0.845509000 -0.880026000 2.875090000
1 -0.054841000 -1.485146000 3.052121000
1 1.740424000 -1.497849000 3.016653000
1 0.867712000 -0.042659000 3.584306000
1 -2.786442000 -0.361801000 0.000000000
74 -0.112163000 0.183642000 0.000000000
E = -392.7984133
3, 3-dimethyle cyclopropene
6 1.286339000 -0.000003000 0.661260000
6 -0.108634000 0.000000000 0.000000000
6 1.286339000 -0.000002000 -0.661259000
1 1.844836000 0.000007000 1.584410000
1 1.844840000 0.000003000 -1.584407000
6 -0.952291000 1.280417000 0.000000000
1 -0.319138000 2.175388000 -0.000003000
1 -1.602034000 1.320102000 -0.886980000
1 -1.602028000 1.320105000 0.886984000
6 -0.952296000 -1.280414000 0.000000000
1 -1.602037000 -1.320098000 0.886980000
1 -1.602036000 -1.320098000 -0.886984000
1 -0.319144000 -2.175387000 0.000000000
E = -195.2115714
CNO Face
SCTS
7 -0.077971000 -1.431167000 -1.122573000
1 0.193742000 -1.973461000 -1.936933000
8 -2.495155000 -0.149988000 -0.242061000
8 -0.669732000 1.775047000 0.056926000
6 -0.338953000 -0.953504000 1.702267000
6 -3.465798000 -1.200548000 -0.055728000
1 -4.465187000 -0.777864000 -0.216826000
1 -3.291006000 -2.014040000 -0.775367000
1 -3.393288000 -1.606550000 0.964976000
6 -1.588816000 2.875278000 -0.062929000
1 -1.547117000 3.481124000 0.851898000
1 -1.308796000 3.503022000 -0.919419000
1 -2.607626000 2.487547000 -0.203643000
1 -0.606151000 -0.390844000 2.607863000
6 2.094183000 0.820067000 0.665668000
6 3.184469000 -0.025114000 -0.023771000
6 2.044088000 0.795315000 -0.669647000
1 1.772804000 1.300183000 1.575024000
1 1.677599000 1.261122000 -1.571039000
6 3.167637000 -1.553493000 0.022004000
1 3.708172000 -1.913747000 0.909538000
1 3.671676000 -1.969269000 -0.863251000
1 2.147496000 -1.942933000 0.053399000
6 4.604174000 0.557753000 -0.085041000
1 5.189804000 0.243710000 0.791012000
1 5.131066000 0.197964000 -0.980557000
1 4.591977000 1.654014000 -0.113186000
1 0.041059000 -1.957561000 1.894783000
74 -0.584422000 -0.141341000 -0.022785000
E = -587.9964824
STBP
7 -0.127834000 -1.866391000 0.340944000
1 -0.098636000 -2.859511000 0.553834000
8 -2.277529000 -0.415532000 -0.437643000
8 -0.992738000 1.728692000 0.008637000
6 0.866183000 0.393206000 1.731872000
6 -3.086972000 -1.592715000 -0.635459000
1 -3.849722000 -1.649846000 0.153731000
1 -3.590139000 -1.516321000 -1.608890000
1 -2.473659000 -2.505817000 -0.614338000
6 -2.157530000 2.554034000 -0.076405000
1 -2.327897000 3.067683000 0.881637000
1 -2.012447000 3.313604000 -0.857881000
1 -3.031919000 1.935587000 -0.322744000
1 0.553775000 1.223534000 2.364218000
6 1.733884000 0.867612000 0.577190000
6 2.649440000 0.000134000 -0.328123000
6 1.290486000 0.333944000 -0.950153000
1 1.868416000 1.944746000 0.545090000
1 1.284607000 1.131951000 -1.693528000
6 3.035720000 -1.406150000 0.122104000
1 3.841837000 -1.352980000 0.866613000
1 3.405113000 -1.980507000 -0.738016000
1 2.192574000 -1.948825000 0.552124000
6 3.836953000 0.747228000 -0.950145000
1 4.678871000 0.791221000 -0.246487000
1 4.179753000 0.229217000 -1.855864000
1 3.571194000 1.775278000 -1.227652000
1 1.222634000 -0.463838000 2.299700000
74 -0.423870000 -0.134587000 0.068224000
E = -588.0701689
SSP
7 0.338465000 -0.366729000 1.944488000
1 0.321464000 -0.455740000 2.953569000
8 1.010127000 1.856448000 -0.016573000
8 2.131497000 -0.758932000 -0.453825000
6 -0.500475000 -1.583246000 -0.790804000
6 0.791155000 3.180952000 -0.514217000
1 1.668245000 3.488315000 -1.097940000
1 -0.099071000 3.216236000 -1.157927000
1 0.657210000 3.870385000 0.329047000
6 2.921155000 -1.800444000 -1.033855000
1 2.286918000 -2.490808000 -1.608542000
1 3.664293000 -1.352712000 -1.705462000
1 3.437193000 -2.358669000 -0.241707000
1 0.130060000 -1.913181000 -1.627436000
6 -1.660566000 -0.713169000 -1.255779000
6 -2.645644000 -0.255212000 -0.196080000
6 -1.378267000 0.604427000 -0.432677000
1 -1.965028000 -0.702922000 -2.301626000
1 -1.560832000 1.606466000 -0.824799000
6 -2.890772000 -1.035695000 1.091480000
1 -3.604146000 -1.854312000 0.913226000
1 -3.322243000 -0.374303000 1.856718000
1 -1.971465000 -1.459361000 1.502499000
6 -3.926894000 0.386942000 -0.741371000
1 -4.702497000 -0.373848000 -0.909953000
1 -4.326534000 1.122145000 -0.028433000
1 -3.748546000 0.902820000 -1.694162000
1 -0.773959000 -2.456812000 -0.187892000
74 0.569575000 0.036026000 0.259762000
E = -588.0764467
SRTS
7 0.102371000 -1.117514000 -1.577792000
1 -0.005936000 -1.525005000 -2.501494000
8 2.010805000 -0.841175000 0.615939000
8 1.326895000 1.641253000 0.018540000
6 -1.439822000 1.376733000 -1.432387000
6 2.403522000 -2.221786000 0.802969000
1 3.416233000 -2.235082000 1.221941000
1 1.709564000 -2.719466000 1.495539000
1 2.391778000 -2.754102000 -0.158128000
6 2.458129000 2.224543000 0.692825000
1 2.999685000 2.874650000 -0.006430000
1 2.111680000 2.826531000 1.544931000
1 3.124933000 1.428078000 1.053011000
1 -1.011171000 2.337386000 -1.701706000
6 -1.941033000 1.192840000 -0.152448000
6 -2.464691000 -0.102506000 0.498623000
6 -1.031203000 -0.358548000 1.035744000
1 -1.841825000 2.024293000 0.547046000
1 -0.878877000 -0.058176000 2.083716000
6 -3.039912000 -1.152347000 -0.465852000
1 -3.931475000 -0.760982000 -0.974954000
1 -3.330504000 -2.047263000 0.098358000
1 -2.305307000 -1.455934000 -1.216195000
6 -3.470854000 0.192538000 1.630785000
1 -4.434571000 0.526365000 1.223480000
1 -3.645850000 -0.713237000 2.225394000
1 -3.097552000 0.974015000 2.306608000
1 -1.648600000 0.683497000 -2.238544000
74 0.461011000 -0.066114000 -0.198587000
E = -588.05902
SROP
7 -0.569851000 -0.016316000 1.961633000
1 -0.527893000 -0.042254000 2.972970000
8 -2.051332000 -1.185609000 -0.481350000
8 -1.350306000 1.801435000 -0.399621000
6 4.083642000 1.277622000 -0.279209000
6 -2.262812000 -2.467852000 -1.094211000
1 -3.098775000 -2.386274000 -1.799712000
1 -1.358120000 -2.790887000 -1.629926000
1 -2.513147000 -3.208809000 -0.323871000
6 -0.934417000 3.065077000 -0.946780000
1 -1.691679000 3.401813000 -1.665391000
1 -0.848501000 3.804492000 -0.140184000
1 0.037072000 2.962045000 -1.450944000
1 4.668490000 1.964374000 -0.887957000
6 3.212699000 0.416167000 -0.843883000
6 2.320605000 -0.613966000 -0.140145000
6 0.870344000 -0.282462000 -0.523043000
1 3.107893000 0.422578000 -1.933718000
1 0.739990000 -0.235610000 -1.628516000
6 2.542750000 -0.637654000 1.385160000
1 3.587017000 -0.885986000 1.616592000
1 1.895342000 -1.390429000 1.847794000
1 2.301369000 0.330029000 1.838363000
6 2.669262000 -2.021987000 -0.726470000
1 3.713168000 -2.281601000 -0.505806000
1 2.014805000 -2.785189000 -0.286913000
1 2.535742000 -2.043125000 -1.816642000
1 4.239898000 1.328509000 0.795201000
74 -0.846122000 0.089382000 0.234142000
E = -588.0984666
ACTS
7 -0.873324000 -1.738830000 -0.902437000
1 -1.051790000 -2.448498000 -1.606825000
8 -2.394410000 0.505109000 -0.126311000
8 -0.028225000 1.605293000 -0.172548000
6 -0.425673000 -0.831535000 1.791937000
6 -3.654627000 -0.127691000 0.171825000
1 -4.459240000 0.582643000 -0.056264000
1 -3.783532000 -1.036965000 -0.435617000
1 -3.700708000 -0.405154000 1.236576000
6 -0.509149000 2.929171000 -0.455919000
1 -0.160260000 3.613008000 0.329275000
1 -0.121055000 3.271311000 -1.425008000
1 -1.607685000 2.917566000 -0.476846000
1 -0.282889000 -0.094584000 2.593574000
6 2.051893000 -1.211968000 0.147708000
6 3.034436000 -0.032494000 0.030624000
6 1.918061000 -0.454390000 -0.955678000
1 1.859290000 -2.165461000 0.610962000
1 1.625908000 -0.428225000 -1.994727000
6 4.479456000 -0.370673000 -0.367535000
1 5.097408000 -0.543651000 0.525236000
1 4.928701000 0.464769000 -0.923062000
1 4.530703000 -1.266612000 -0.998410000
6 2.939392000 1.198147000 0.930926000
1 3.481114000 1.019314000 1.871451000
1 3.402512000 2.065667000 0.438595000
1 1.903875000 1.455715000 1.157307000
1 -0.489209000 -1.864414000 2.137125000
74 -0.603805000 -0.222152000 -0.027551000
E = -587.9936051
ATBP
7 -1.018954000 -1.930993000 0.305808000
1 -1.538695000 -2.785629000 0.486556000
8 -2.221543000 0.335477000 -0.548462000
8 -0.295401000 1.682023000 0.313256000
6 0.944995000 -0.253480000 1.775026000
6 -3.360543000 -0.408191000 -1.018835000
1 -4.276760000 0.072025000 -0.649399000
1 -3.379911000 -0.409754000 -2.118287000
1 -3.328312000 -1.451197000 -0.663936000
6 -1.005291000 2.901249000 0.056982000
1 -1.139608000 3.457511000 0.995440000
1 -0.422823000 3.520344000 -0.640937000
1 -1.982550000 2.667557000 -0.384079000
1 1.131199000 0.766280000 2.106660000
6 1.841063000 -0.791122000 0.679126000
6 2.552706000 0.032708000 -0.424965000
6 1.247250000 -0.626466000 -0.896875000
1 2.168838000 -1.816755000 0.826131000
1 1.368624000 -1.531070000 -1.490425000
6 3.820357000 -0.620441000 -0.993481000
1 4.687183000 -0.393821000 -0.358701000
1 4.028367000 -0.233367000 -1.999818000
1 3.724070000 -1.711799000 -1.062612000
6 2.718548000 1.542186000 -0.255684000
1 3.547110000 1.749060000 0.436007000
1 2.967962000 1.992399000 -1.226219000
1 1.810899000 2.016578000 0.119251000
1 0.826133000 -0.959267000 2.595072000
74 -0.479432000 -0.246362000 0.124899000
E = -588.0680069
ASP
7 -1.336154000 0.400248000 -1.872356000
1 -1.872810000 0.635041000 -2.698915000
8 -0.357712000 1.800711000 0.648132000
8 -1.815470000 -0.687772000 0.931802000
6 0.275559000 -1.803603000 -0.577404000
6 0.495078000 2.850951000 1.124595000
1 0.361378000 2.957669000 2.208487000
1 1.544040000 2.611983000 0.906137000
1 0.221213000 3.792320000 0.631227000
6 -2.401790000 -1.816498000 1.589780000
1 -1.733434000 -2.686486000 1.531202000
1 -2.574823000 -1.562810000 2.643084000
1 -3.360139000 -2.062666000 1.114430000
1 0.226127000 -2.482280000 0.285708000
6 1.664456000 -1.282108000 -0.928405000
6 2.402424000 -0.529333000 0.181243000
6 1.444710000 0.243828000 -0.760249000
1 2.248771000 -1.725337000 -1.734205000
1 1.877530000 0.997124000 -1.418971000
6 3.889180000 -0.278590000 -0.085212000
1 4.498094000 -1.121108000 0.274455000
1 4.235648000 0.628937000 0.430789000
1 4.089353000 -0.152187000 -1.156942000
6 2.108005000 -0.752755000 1.665570000
1 2.686096000 -1.606262000 2.049776000
1 2.390770000 0.133252000 2.252647000
1 1.049885000 -0.957370000 1.867994000
1 -0.223823000 -2.279849000 -1.429006000
74 -0.651231000 0.180857000 -0.277708000
E = -588.0773095
ARTS
7 1.047944000 -1.091050000 -1.686833000
1 1.605845000 -1.433602000 -2.462915000
8 1.930385000 -0.477818000 0.925243000
8 0.725427000 1.734440000 0.192116000
6 -1.611362000 1.400265000 -1.406380000
6 2.369414000 -1.763615000 1.415737000
1 3.158126000 -1.592704000 2.158640000
1 1.534085000 -2.306347000 1.884538000
1 2.770333000 -2.371008000 0.589265000
6 1.784105000 2.482120000 0.841228000
1 2.346251000 3.050408000 0.088307000
1 1.323827000 3.184349000 1.548239000
1 2.454872000 1.795227000 1.371941000
1 -1.307175000 2.216343000 -0.762971000
6 -2.256015000 0.275031000 -0.941256000
6 -2.375726000 -0.220643000 0.514240000
6 -1.093619000 -1.075058000 0.312992000
1 -2.608799000 -0.450033000 -1.677103000
1 -1.291869000 -2.105012000 0.002427000
6 -3.635341000 -1.085865000 0.723798000
1 -4.543885000 -0.469103000 0.700570000
1 -3.590225000 -1.591606000 1.696747000
1 -3.725647000 -1.856600000 -0.053438000
6 -2.301307000 0.884041000 1.587630000
1 -3.188748000 1.529108000 1.534730000
1 -2.267446000 0.424049000 2.582980000
1 -1.412046000 1.513177000 1.480410000
1 -1.512825000 1.555797000 -2.477866000
74 0.491788000 -0.120077000 -0.319236000
E = -588.0565862
AROP
7 1.821467000 0.428811000 -1.687493000
1 2.450191000 0.617168000 -2.458596000
8 1.542255000 -1.202582000 0.912285000
8 0.602562000 1.714678000 0.830368000
6 -3.920524000 1.060872000 0.177679000
6 1.710031000 -2.585127000 1.257624000
1 1.822511000 -2.665224000 2.345829000
1 0.837382000 -3.170585000 0.934354000
1 2.611116000 -2.982201000 0.772143000
6 -0.110604000 2.939208000 1.079701000
1 -1.137299000 2.864643000 0.698497000
1 -0.128046000 3.119630000 2.161560000
1 0.405303000 3.771801000 0.584128000
1 -3.836163000 1.062051000 1.261713000
6 -3.163664000 0.267415000 -0.609231000
6 -2.094473000 -0.740882000 -0.176181000
6 -0.801416000 -0.372436000 -0.945010000
1 -3.305680000 0.321650000 -1.692634000
1 -0.938247000 -0.432562000 -2.029773000
6 -2.553963000 -2.156472000 -0.653671000
1 -3.490227000 -2.446312000 -0.157612000
1 -1.784002000 -2.903473000 -0.421589000
1 -2.722865000 -2.171478000 -1.738415000
6 -1.905791000 -0.769212000 1.358950000
1 -2.845587000 -1.036109000 1.859178000
1 -1.154017000 -1.516716000 1.638559000
1 -1.579684000 0.202956000 1.748496000
1 -4.656486000 1.737924000 -0.251233000
74 0.899803000 0.171192000 -0.220575000
E = -588.0969192
COO Face
COO_TS
7 2.353101000 0.660145000 -0.354714000
1 3.306838000 0.962176000 -0.167101000
8 1.070913000 -1.744137000 -0.197802000
8 -0.150264000 1.761066000 -0.245031000
6 0.349259000 0.000908000 2.028961000
6 0.145118000 3.011854000 -0.887870000
1 1.222025000 3.065073000 -1.107120000
1 -0.429414000 3.094426000 -1.819728000
1 -0.141983000 3.830671000 -0.215802000
6 2.145819000 -2.520720000 -0.751929000
1 2.449845000 -3.278814000 -0.018076000
1 1.807200000 -3.027367000 -1.665854000
1 2.997269000 -1.863191000 -0.985060000
1 0.684526000 -0.834369000 2.652896000
6 -1.663363000 -1.215479000 0.497730000
6 -2.814647000 -0.395880000 -0.103127000
6 -1.504061000 -0.843581000 -0.802704000
1 -1.438916000 -1.993193000 1.209852000
1 -1.173237000 -1.247342000 -1.749795000
6 -3.116141000 1.041391000 0.316205000
1 -3.775876000 1.042993000 1.196740000
1 -3.640914000 1.570386000 -0.493353000
1 -2.205164000 1.592892000 0.547979000
6 -4.087806000 -1.183708000 -0.455144000
1 -4.783638000 -1.199690000 0.396109000
1 -4.608880000 -0.707507000 -1.298041000
1 -3.863859000 -2.220502000 -0.735441000
1 -0.011812000 0.861548000 2.602004000
74 0.716811000 0.111171000 0.116523000
E = -587.9791255
COO_TBP
7 2.298747000 0.703767000 -0.033983000
1 3.234666000 0.901366000 -0.384073000
8 1.195639000 -1.732786000 -0.139929000
8 -0.135314000 1.853599000 -0.177688000
6 -0.559886000 -0.264077000 1.750538000
6 0.338035000 3.203675000 -0.280436000
1 1.436157000 3.213780000 -0.197985000
1 0.028185000 3.627652000 -1.244524000
1 -0.098769000 3.803190000 0.529661000
6 2.454357000 -2.411551000 -0.236406000
1 2.506974000 -3.183609000 0.542995000
1 2.537851000 -2.897207000 -1.218448000
1 3.283847000 -1.698328000 -0.102751000
1 -0.142524000 -0.899413000 2.531079000
6 -1.431027000 -1.029903000 0.768100000
6 -2.514883000 -0.434776000 -0.172512000
6 -1.169621000 -0.709159000 -0.849719000
1 -1.443354000 -2.102287000 0.942313000
1 -1.137230000 -1.621564000 -1.447159000
6 -3.050495000 0.972876000 0.091990000
1 -3.767219000 0.952717000 0.925577000
1 -3.581496000 1.332857000 -0.800182000
1 -2.254719000 1.685212000 0.309779000
6 -3.643925000 -1.407831000 -0.541477000
1 -4.425694000 -1.411209000 0.230701000
1 -4.108323000 -1.105582000 -1.490143000
1 -3.273770000 -2.434508000 -0.658510000
1 -0.959587000 0.669365000 2.148757000
74 0.608863000 0.104854000 -0.013767000
E = -588.0517616
1