"Radicals and Radical Ions Derived from Indole, Indole-3-carbinol and Diindolylmethane" Anna Bloch-Mechkour, Thomas Bally,* Adam Sikora, Jerzy Gebicki, Radoslaw Michalski and Andrzej Marcinek* ========================================================== SUPPORTING INFORMATION ========================================================== All stationary points listed in this file were located and characterized by B3LYP/6-31G*. The charge and multiplicity are indicated in the line above the cartesian coordinates. ------------------------------------------------------- indole neutral ------------------------------------------------------- 0,1 C 0.00000000 0.71579300 0.00000000 C -0.49512800 -0.61928400 0.00000000 C -1.92984800 -0.53162900 0.00000000 C -2.25291500 0.79925700 0.00000000 C 0.42721800 -1.68075400 0.00000000 C 1.78645900 -1.39620700 0.00000000 C 2.25277000 -0.06494000 0.00000000 C 1.36835200 1.00724400 0.00000000 N -1.09524000 1.55641900 0.00000000 H 0.07864100 -2.71054600 0.00000000 H 2.50605800 -2.21046000 0.00000000 H 3.32244100 0.12617200 0.00000000 H 1.72802300 2.03325600 0.00000000 H -3.22086200 1.28112800 0.00000000 H -2.63110600 -1.35487000 0.00000000 H -1.05796800 2.56351300 0.00000000 SCF Done: E(RB+HF-LYP) = -363.816689044 Sum of electronic and zero-point Energies= -363.686755 Sum of electronic and thermal Energies= -363.680428 Sum of electronic and thermal Enthalpies= -363.679484 Sum of electronic and thermal Free Energies= -363.717091 ------------------------------------------------------- indole radical cation ------------------------------------------------------- 1,2 C 0.00000000 0.72000200 0.00000000 C -0.48909700 -0.62029100 0.00000000 C -1.89424900 -0.55401200 0.00000000 C -2.24359800 0.82620800 0.00000000 C 0.43674900 -1.69503200 0.00000000 C 1.80235000 -1.40126500 0.00000000 C 2.24605700 -0.07604700 0.00000000 C 1.34011600 1.02264400 0.00000000 N -1.12810000 1.56273400 0.00000000 H 0.08729700 -2.72281800 0.00000000 H 2.52657200 -2.20861800 0.00000000 H 3.31112500 0.13313700 0.00000000 H 1.71208300 2.04241400 0.00000000 H -3.22630200 1.27928100 0.00000000 H -2.60169500 -1.37250100 0.00000000 H -1.10235100 2.57671700 0.00000000 SCF Done: E(UB+HF-LYP) = -363.549698906 Sum of electronic and zero-point Energies= -363.419387 Sum of electronic and thermal Energies= -363.413133 Sum of electronic and thermal Enthalpies= -363.412189 Sum of electronic and thermal Free Energies= -363.450368 ------------------------------------------------------- 1-indolyl radical ------------------------------------------------------- 0,2 C 0.00000000 0.74567200 0.00000000 C -0.53838500 -0.57794200 0.00000000 C -1.95327800 -0.39271900 0.00000000 C -2.15250900 1.03133300 0.00000000 C 0.31288900 -1.68751700 0.00000000 C 1.69946500 -1.46692000 0.00000000 C 2.21413900 -0.16951200 0.00000000 C 1.36292600 0.95977000 0.00000000 N -1.02670800 1.71957600 0.00000000 H -0.08302500 -2.69998900 0.00000000 H 2.37818700 -2.31481900 0.00000000 H 3.29054500 -0.02149900 0.00000000 H 1.76590200 1.96804200 0.00000000 H -3.11424300 1.53503200 0.00000000 H -2.72188900 -1.15679100 0.00000000 SCF Done: E(UB+HF-LYP) = -363.166639431 Sum of electronic and zero-point Energies= -363.050441 Sum of electronic and thermal Energies= -363.044338 Sum of electronic and thermal Enthalpies= -363.043393 Sum of electronic and thermal Free Energies= -363.081304 ------------------------------------------------------- indole-3-carbinol (I3C) neutral ------------------------------------------------------- 0,1 C 0.00000000 0.39984300 0.00000000 C 1.24481100 -0.29114800 0.00000000 C 2.47123400 0.38082100 0.00000000 C 2.44411400 1.77107000 0.00000000 C 1.22389700 2.47707400 0.00000000 C 0.00716500 1.80592900 0.00000000 C -1.03736600 -0.60064900 0.00000000 C -0.41235700 -1.81946300 0.00000000 C -2.51460400 -0.36354100 0.00000000 N 0.96019800 -1.64064100 0.00000000 O -3.18088200 -1.62325900 0.00000000 H 3.41275600 -0.16281400 0.00000000 H 3.38043300 2.32250000 0.00000000 H 1.23857200 3.56364100 0.00000000 H -0.92596300 2.36413500 0.00000000 H -0.84802300 -2.80718900 0.00000000 H 1.64204900 -2.38246100 0.00000000 H -2.80088900 0.23210600 0.88459500 H -4.13373500 -1.45108400 0.00000000 H -2.80088900 0.23210600 -0.88459500 SCF Done: E(RB+HF-LYP) = -478.336520740 Sum of electronic and zero-point Energies= -478.174033 Sum of electronic and thermal Energies= -478.164770 Sum of electronic and thermal Enthalpies= -478.163826 Sum of electronic and thermal Free Energies= -478.208875 ------------------------------------------------------- indole-3-carbinol (I3C) radical cation ------------------------------------------------------- 1,2 C 0.00000000 0.42235100 0.00000000 C 1.22414600 -0.30213200 0.00000000 C 2.45724300 0.30889900 0.00000000 C 2.46757000 1.72598800 0.00000000 C 1.28418100 2.46982900 0.00000000 C 0.03956200 1.83378700 0.00000000 C -1.05493500 -0.52997000 0.00000000 C -0.43643400 -1.81838000 0.00000000 C -2.53171100 -0.32682400 0.00000000 N 0.88978900 -1.67182700 0.00000000 O -3.13824500 -1.59871200 0.00000000 H 3.38659600 -0.25195700 0.00000000 H 3.42373400 2.23947600 0.00000000 H 1.33311300 3.55337700 0.00000000 H -0.87579500 2.41753000 0.00000000 H -0.92330900 -2.78332000 0.00000000 H 1.55675600 -2.43590500 0.00000000 H -2.80966500 0.27321900 0.88456600 H -4.10205800 -1.49444100 0.00000000 H -2.80966500 0.27321900 -0.88456600 SCF Done: E(UB+HF-LYP) = -478.079312501 Sum of electronic and zero-point Energies= -477.916608 Sum of electronic and thermal Energies= -477.907536 Sum of electronic and thermal Enthalpies= -477.906592 Sum of electronic and thermal Free Energies= -477.951685 ------------------------------------------------------- indole-3-carbinol indolyl radical (I3C-N.) ------------------------------------------------------- 0,2 C 0.00000000 0.40469100 0.00000000 C 1.23425100 -0.31003900 0.00000000 C 2.44399400 0.35726000 0.00000000 C 2.42607100 1.76824400 0.00000000 C 1.22325600 2.47729100 0.00000000 C -0.00730200 1.80154600 0.00000000 C -1.01242700 -0.61545400 0.00000000 C -0.28953000 -1.85977500 0.00000000 C -2.48904900 -0.42991800 0.00000000 N 1.02178300 -1.70748600 0.00000000 O -3.12312500 -1.69927100 0.00000000 H 3.37883400 -0.19506800 0.00000000 H 3.36698800 2.31172600 0.00000000 H 1.23860800 3.56340200 0.00000000 H -0.93786700 2.36441700 0.00000000 H -0.74833800 -2.84131100 0.00000000 H -2.78027900 0.16762500 0.88355600 H -4.08074400 -1.55492200 0.00000000 H -2.78027900 0.16762500 -0.88355600 SCF Done: E(UB+HF-LYP) = -477.689031392 Sum of electronic and zero-point Energies= -477.540240 Sum of electronic and thermal Energies= -477.531222 Sum of electronic and thermal Enthalpies= -477.530278 Sum of electronic and thermal Free Energies= -477.575684 ------------------------------------------------------- indole-3-carbinol ketyl radical (I3C-C.) ------------------------------------------------------- 0,2 C 0.00000000 0.38099000 0.00000000 C -1.18732900 -0.39750200 0.00000000 C -2.45817300 0.18474700 0.00000000 C -2.53222100 1.57471400 0.00000000 C -1.36845100 2.36524100 0.00000000 C -0.10595700 1.77703600 0.00000000 C 1.12825600 -0.54718300 0.00000000 C 0.56628000 -1.83077400 0.00000000 C 2.48492100 -0.21463400 0.00000000 N -0.81575000 -1.72746800 0.00000000 O 3.41675700 -1.22677700 0.00000000 H -3.35778800 -0.42555100 0.00000000 H -3.50658000 2.05591200 0.00000000 H -1.45772100 3.44803900 0.00000000 H 0.78542000 2.39981300 0.00000000 H 1.05622400 -2.79212900 0.00000000 H -1.45242400 -2.50819200 0.00000000 H 4.30149900 -0.83579600 0.00000000 H 2.84360300 0.80858100 0.00000000 SCF Done: E(UB+HF-LYP) = -477.697558296 Sum of electronic and zero-point Energies= -477.549195 Sum of electronic and thermal Energies= -477.539746 Sum of electronic and thermal Enthalpies= -477.538802 Sum of electronic and thermal Free Energies= -477.584126 ------------------------------------------------------- Diindolylmethane (DIM) eutral C1 symmetry ------------------------------------------------------- 0,1 C -2.45356900 0.28396600 -0.19185700 C -3.01301700 -0.59242500 0.77979000 C -4.35754000 -0.97652900 0.75355300 C -5.15222200 -0.46753200 -0.26792400 C -4.62103400 0.40381100 -1.24060200 C -3.28423200 0.78246800 -1.21039900 C -1.05895900 0.45803700 0.13774000 C -0.83162200 -0.29391900 1.26170600 C -0.07511800 1.32610300 -0.60915900 N -2.00005900 -0.92435600 1.65501500 H -4.76823800 -1.64805700 1.50354900 H -6.20128300 -0.74686600 -0.31647000 H -5.27023800 0.78359600 -2.02500700 H -2.88698900 1.45526900 -1.96648300 H 0.08454000 -0.43668100 1.81650900 H -2.08341200 -1.55759400 2.43429400 H -0.14821600 1.09710700 -1.68364500 H -0.37687500 2.38010100 -0.51957500 C 1.35833600 1.19504100 -0.17112900 C 2.10838200 2.15528300 0.45898200 H 1.82731800 3.15446400 0.76433800 N 3.39044700 1.68695800 0.68796600 H 4.13409600 2.21201400 1.11992800 C 2.22848400 0.05522800 -0.34739500 C 2.06277300 -1.21905200 -0.91886900 C 3.49575400 0.40076500 0.19926800 C 3.13896200 -2.09732300 -0.93528900 H 1.10233200 -1.51243800 -1.33361700 C 4.58170200 -0.48119400 0.18693200 C 4.38628400 -1.73182400 -0.38772700 H 3.02091700 -3.08403700 -1.37501700 H 5.54339400 -0.20010000 0.60904500 H 5.20975500 -2.44041400 -0.41444400 SCF Done: E(RB+HF-LYP) = -765.753250037 Sum of electronic and zero-point Energies= -765.484639 Sum of electronic and thermal Energies= -765.470067 Sum of electronic and thermal Enthalpies= -765.469123 Sum of electronic and thermal Free Energies= -765.527705 ------------------------------------------------------- Diindolylmethane neutral C2 symmetry ------------------------------------------------------- 0,1 C 0.00000000 2.59969600 0.35525600 C -0.50419500 3.46282600 -0.65762000 C -0.37652100 4.85410300 -0.58841300 C 0.26767000 5.38559400 0.52283200 C 0.77337100 4.55142400 1.54124600 C 0.64381300 3.17029100 1.46766500 C -0.29508300 1.24434200 -0.04492000 C -0.95206900 1.33440400 -1.24710400 C 0.00000000 0.00000000 0.75551100 N -1.08253900 2.66142200 -1.61919300 H -0.76727000 5.49723500 -1.37311800 H 0.38245400 6.46280600 0.60810100 H 1.27036900 4.99997600 2.39719900 H 1.03574100 2.53964700 2.26172600 H -1.34392100 0.54732500 -1.87564500 H -1.51070700 2.98617000 -2.47160900 H 0.84511500 0.21186100 1.42751600 H -0.84511500 -0.21186100 1.42751600 C 0.29508300 -1.24434200 -0.04492000 C 0.95206900 -1.33440400 -1.24710400 H 1.34392100 -0.54732500 -1.87564500 N 1.08253900 -2.66142200 -1.61919300 H 1.51070700 -2.98617000 -2.47160900 C 0.00000000 -2.59969600 0.35525600 C -0.64381300 -3.17029100 1.46766500 C 0.50419500 -3.46282600 -0.65762000 C -0.77337100 -4.55142400 1.54124600 H -1.03574100 -2.53964700 2.26172600 C 0.37652100 -4.85410300 -0.58841300 C -0.26767000 -5.38559400 0.52283200 H -1.27036900 -4.99997600 2.39719900 H 0.76727000 -5.49723500 -1.37311800 H -0.38245400 -6.46280600 0.60810100 SCF Done: E(RB+HF-LYP) = -765.751297645 Sum of electronic and zero-point Energies= -765.482676 Sum of electronic and thermal Energies= -765.468089 Sum of electronic and thermal Enthalpies= -765.467145 Sum of electronic and thermal Free Energies= -765.525494 ------------------------------------------------------- Diindolylmethane radical cation CS symmetry ------------------------------------------------------- 1,2 C -0.04450200 0.40210500 1.94363100 C 0.34919800 -0.53625000 2.93395400 C -0.53610800 -1.07336800 3.85826900 C -1.87076600 -0.65504300 3.77907500 C -2.28939500 0.27536200 2.81553600 C -1.38935400 0.81258600 1.89701200 C 1.13241800 0.75657500 1.20085600 C 2.18510700 0.01296500 1.75807200 C 1.24756700 1.65731900 0.00000000 N 1.72045600 -0.74402300 2.77913800 H -0.21531400 -1.78063000 4.61705400 H -2.59173200 -1.05419800 4.48540100 H -3.32925900 0.58473500 2.79117200 H -1.72389600 1.54522400 1.16971800 H 3.23324800 0.00545200 1.49121500 H 2.29020100 -1.33662800 3.36840100 H 0.45901000 2.41502800 0.00000000 H 2.20355000 2.19027900 0.00000000 C 1.13241800 0.75657500 -1.20085600 C 2.18510700 0.01296500 -1.75807200 H 3.23324800 0.00545200 -1.49121500 N 1.72045600 -0.74402300 -2.77913800 H 2.29020100 -1.33662800 -3.36840100 C -0.04450200 0.40210500 -1.94363100 C -1.38935400 0.81258600 -1.89701200 C 0.34919800 -0.53625000 -2.93395400 C -2.28939500 0.27536200 -2.81553600 H -1.72389600 1.54522400 -1.16971800 C -0.53610800 -1.07336800 -3.85826900 C -1.87076600 -0.65504300 -3.77907500 H -3.32925900 0.58473500 -2.79117200 H -0.21531400 -1.78063000 -4.61705400 H -2.59173200 -1.05419800 -4.48540100 SCF Done: E(UB+HF-LYP) = -765.514495009 Sum of electronic and zero-point Energies= -765.244808 Sum of electronic and thermal Energies= -765.231527 Sum of electronic and thermal Enthalpies= -765.230583 Sum of electronic and thermal Free Energies= -765.285629 ------------------------------------------------------- Diindolylmethane radical cation C2 symmetry ------------------------------------------------------- 1,2 C 0.00000000 2.45537700 0.39902000 C 0.00000000 -2.45537700 0.39902000 C -0.77354800 3.11548000 -0.59302000 C 0.77354800 -3.11548000 -0.59302000 C -0.58735600 4.45032700 -0.92531000 C 0.58735600 -4.45032700 -0.92531000 C 0.41998100 5.14132800 -0.23998000 C -0.41998100 -5.14132800 -0.23998000 C 1.20355300 4.51387900 0.74306000 C -1.20355300 -4.51387900 0.74306000 C 1.00594500 3.17558500 1.07145000 C -1.00594500 -3.17558500 1.07145000 C 0.48946800 -1.11155900 0.49517000 C -0.48946800 1.11155900 0.49517000 C 1.51940700 -0.99738100 -0.45363000 C -1.51940700 0.99738100 -0.45363000 C 0.00000000 0.00000000 1.37743000 N -1.68737600 2.18209500 -1.08603000 N 1.68737600 -2.18209500 -1.08603000 H -1.19383900 4.94569000 -1.67738000 H 1.19383900 -4.94569000 -1.67738000 H 0.59508800 6.18654500 -0.47450000 H -0.59508800 -6.18654500 -0.47450000 H 1.97313800 5.08399900 1.25325000 H -1.97313800 -5.08399900 1.25325000 H 1.61773500 2.70100700 1.83341000 H -1.61773500 -2.70100700 1.83341000 H -2.13708500 0.14196200 -0.69081000 H 2.13708500 -0.14196200 -0.69081000 H -2.38726700 2.36832500 -1.79197000 H 2.38726700 -2.36832500 -1.79197000 H 0.79539800 0.36477600 2.03734000 H -0.79539800 -0.36477600 2.03734000 SCF Done: E(UB+HF-LYP) = -765.516915357 Sum of electronic and zero-point Energies= -765.247310 Sum of electronic and thermal Energies= -765.233051 Sum of electronic and thermal Enthalpies= -765.232107 Sum of electronic and thermal Free Energies= -765.290616 ------------------------------------------------------- Diindolylmethane C-radical C2 symmetry (conformer 1) ------------------------------------------------------- 0,2 C 0.00000000 2.55721300 0.31203600 C -0.18195000 3.58103900 -0.65202400 C -0.14165700 4.93847100 -0.32129200 C 0.08542600 5.26774700 1.01134800 C 0.27215800 4.26897800 1.98594900 C 0.23462000 2.92024100 1.64516500 C -0.10079300 1.27308700 -0.37613600 C -0.33891900 1.59264000 -1.71489900 C 0.00000000 0.00000000 0.24657300 N -0.38491200 2.96413200 -1.87212500 H -0.28301000 5.70878500 -1.07519800 H 0.12084800 6.31388600 1.30312700 H 0.45153400 4.55815500 3.01778500 H 0.38889700 2.15910800 2.40559700 H -0.54995100 0.94467900 -2.55179000 H -0.56471100 3.44012100 -2.74200100 H 0.00000000 0.00000000 1.33351700 C 0.10079300 -1.27308700 -0.37613600 C 0.33891900 -1.59264000 -1.71489900 H 0.54995100 -0.94467900 -2.55179000 N 0.38491200 -2.96413200 -1.87212500 H 0.56471100 -3.44012100 -2.74200100 C 0.00000000 -2.55721300 0.31203600 C -0.23462000 -2.92024100 1.64516500 C 0.18195000 -3.58103900 -0.65202400 C -0.27215800 -4.26897800 1.98594900 H -0.38889700 -2.15910800 2.40559700 C 0.14165700 -4.93847100 -0.32129200 C -0.08542600 -5.26774700 1.01134800 H -0.45153400 -4.55815500 3.01778500 H 0.28301000 -5.70878500 -1.07519800 H -0.12084800 -6.31388600 1.30312700 SCF Done: E(UB+HF-LYP) = -765.121383029 Sum of electronic and zero-point Energies= -764.866230 Sum of electronic and thermal Energies= -764.851739 Sum of electronic and thermal Enthalpies= -764.850795 Sum of electronic and thermal Free Energies= -764.908413 ------------------------------------------------------- Diindolylmethane C-radical C1 symmetry (conformer 2) ------------------------------------------------------- 0,2 C -2.26200200 0.04633700 -0.09509100 C -3.57401800 0.56446800 0.09024600 C -4.72539200 -0.21173400 -0.06983400 C -4.56015300 -1.53903000 -0.44832100 C -3.27635300 -2.06918500 -0.67672000 C -2.13561200 -1.29067600 -0.50979300 C -1.32378900 1.14570200 0.12865200 C -2.12130100 2.25384600 0.40808200 C 0.10394600 1.20967800 0.05998300 N -3.45348400 1.90500000 0.39772500 H -5.71483100 0.21125100 0.08516500 H -5.43447700 -2.17023000 -0.58203200 H -3.17615900 -3.10258500 -0.99750900 H -1.15729000 -1.70949800 -0.71801500 H -1.81707700 3.26674700 0.63308700 H -4.22147600 2.53434300 0.57051100 H 0.51421100 2.20974100 -0.06870000 C 1.06590200 0.17977700 0.23896500 C 0.92160900 -1.10246100 0.77545300 H 0.04200300 -1.58471700 1.17299200 N 2.14890400 -1.73416000 0.82673100 H 2.30348000 -2.66529300 1.17995900 C 2.49316400 0.31690200 -0.04314700 C 3.27177300 1.34592800 -0.58933800 C 3.12882200 -0.89331500 0.33405200 C 4.64300000 1.15716500 -0.73566000 H 2.81088100 2.27919000 -0.90240700 C 4.50377400 -1.09562500 0.18577400 C 5.25204100 -0.05247200 -0.35130000 H 5.25346100 1.95102800 -1.15720100 H 4.97269500 -2.03148500 0.47905800 H 6.32417000 -0.17620600 -0.47811800 SCF Done: E(UB+HF-LYP) = -765.117912405 Sum of electronic and zero-point Energies= -764.862552 Sum of electronic and thermal Energies= -764.848162 Sum of electronic and thermal Enthalpies= -764.847218 Sum of electronic and thermal Free Energies= -764.905001 ------------------------------------------------------- Diindolylmethane C-radical C2 symmetry (conformer 3) ------------------------------------------------------- 0,2 C 0.18147400 1.82077300 0.14060100 C -0.25368500 3.17310000 0.09094900 C 0.00000000 4.00935600 -1.00001500 C 0.72903200 3.48009800 -2.05919800 C 1.20223200 2.15484300 -2.02099800 C 0.94022300 1.32745900 -0.93354900 C -0.23149800 1.27507200 1.43307800 C -0.86657400 2.33070500 2.08771300 C 0.00000000 0.00000000 2.03575200 N -0.88911400 3.45062700 1.28591700 H -0.35015500 5.03850700 -1.01456100 H 0.94442900 4.10278600 -2.92338200 H 1.78509300 1.77283000 -2.85460600 H 1.31852200 0.31161800 -0.91654700 H -1.31513600 2.34623300 3.07142600 H -1.30044000 4.33632900 1.53487400 H 0.00000000 0.00000000 3.12527300 C 0.23149800 -1.27507200 1.43307800 C 0.86657400 -2.33070500 2.08771300 H 1.31513600 -2.34623300 3.07142600 N 0.88911400 -3.45062700 1.28591700 H 1.30044000 -4.33632900 1.53487400 C -0.18147400 -1.82077300 0.14060100 C -0.94022300 -1.32745900 -0.93354900 C 0.25368500 -3.17310000 0.09094900 C -1.20223200 -2.15484300 -2.02099800 H -1.31852200 -0.31161800 -0.91654700 C 0.00000000 -4.00935600 -1.00001500 C -0.72903200 -3.48009800 -2.05919800 H -1.78509300 -1.77283000 -2.85460600 H 0.35015500 -5.03850700 -1.01456100 SCF Done: E(UB+HF-LYP) = -765.114240734 Sum of electronic and zero-point Energies= -764.859037 Sum of electronic and thermal Energies= -764.844633 Sum of electronic and thermal Enthalpies= -764.843689 Sum of electronic and thermal Free Energies= -764.901263 =========================================================== Calculations for three conformers of urorosein were done with the PCM-SCRF model, using ethanol as a solvent. Note that the option "sphereonH" must be specified for the proton that is being transferred, else the cavity defini- tion does not converge at the transition state. To compare energies, this option was used in all the SCRF calculations. ---------------------------------------------------------- Urorosein C2 symmetry (conformer 1) ---------------------------------------------------------- 1,1 C 0.00000000 2.55834800 0.34413100 C 0.26053000 3.54144200 -0.63605700 C 0.20842300 4.91001400 -0.37772900 C -0.11894600 5.29186700 0.92231000 C -0.38758000 4.33232700 1.91635600 C -0.33843400 2.96649500 1.63969400 C 0.13245800 1.25865200 -0.31380600 C 0.49012200 1.54797700 -1.65415000 C 0.00000000 0.00000000 0.28600800 N 0.56013400 2.87184600 -1.82608600 H 0.41264400 5.64300800 -1.15601300 H -0.17074600 6.35013000 1.17077800 H -0.64227900 4.66409800 2.92118100 H -0.55860200 2.23895600 2.41948500 H 0.76297500 0.87790400 -2.46174400 H 0.84698300 3.32837700 -2.70280700 H 0.00000000 0.00000000 1.37843000 C -0.13245800 -1.25865200 -0.31380600 C -0.49012200 -1.54797700 -1.65415000 H -0.76297500 -0.87790400 -2.46174400 N -0.56013400 -2.87184600 -1.82608600 H -0.84698300 -3.32837700 -2.70280700 C 0.00000000 -2.55834800 0.34413100 C 0.33843400 -2.96649500 1.63969400 C -0.26053000 -3.54144200 -0.63605700 C 0.38758000 -4.33232700 1.91635600 H 0.55860200 -2.23895600 2.41948500 C -0.20842300 -4.91001400 -0.37772900 C 0.11894600 -5.29186700 0.92231000 H 0.64227900 -4.66409800 2.92118100 H -0.41264400 -5.64300800 -1.15601300 H 0.17074600 -6.35013000 1.17077800 Total free energy in solution: with all non electrostatic terms -765.016648 Total non electrostatic (kcal/mol) = 2.89 Zero-point correction= 0.256352 Thermal correction to Energy= 0.270092 Thermal correction to Enthalpy= 0.271036 Thermal correction to Gibbs Free Energy= 0.215267 B2PLYP scrf(solvent=ethanol,externalIter) -764.173598 (this calculation was done with Gaussian 09) ---------------------------------------------------------- Urorosein C1 symmetry (conformer 2) ---------------------------------------------------------- 1,1 C 2.29664900 -0.00063000 0.07902300 C 3.55376800 0.62857000 -0.10010100 C 4.77112100 -0.04038500 -0.00632700 C 4.72505800 -1.39907600 0.30157200 C 3.49760100 -2.04354800 0.52928200 C 2.28626700 -1.35937200 0.42605200 C 1.28675700 1.05166300 -0.06947300 C 2.01613300 2.24749400 -0.28940500 C -0.11330000 1.09936400 -0.05876400 N 3.32267200 1.98847800 -0.33235700 H 5.71474100 0.48148000 -0.15530200 H 5.65272500 -1.96226700 0.38224700 H 3.48933200 -3.09844300 0.79679700 H 1.36242400 -1.88271700 0.64640300 H 1.63046600 3.25165400 -0.44365700 H 4.05566900 2.69096300 -0.50080900 H -0.51423100 2.11439700 0.00220000 C -1.09169100 0.10103100 -0.13782700 C -0.95559000 -1.25067900 -0.53628000 H -0.07550900 -1.79684300 -0.84587600 N -2.16003700 -1.82887900 -0.59277800 H -2.32310000 -2.80018900 -0.89168500 C -2.52848800 0.30806700 0.04849400 C -3.31187600 1.39993900 0.44099700 C -3.16131200 -0.92202800 -0.23403400 C -4.69353600 1.23157300 0.52457300 H -2.85969200 2.36167900 0.67880100 C -4.53995000 -1.10905700 -0.14730800 C -5.30017800 -0.00544300 0.23588400 H -5.31653400 2.07282500 0.82264300 H -4.99815900 -2.07115300 -0.36892300 H -6.38117300 -0.10348100 0.31495600 Total free energy in solution: with all non electrostatic terms -765.015943 Total non electrostatic (kcal/mol) = 2.85 Zero-point correction= 0.256631 Thermal correction to Energy= 0.270296 Thermal correction to Enthalpy= 0.271240 Thermal correction to Gibbs Free Energy= 0.215114 B2PLYP scrf(solvent=ethanol,externalIter) -764.173476 (this calculation was done with Gaussian 09) + ---------------------------------------------------------- Urorosein C2 symmetry (conformer 3) ---------------------------------------------------------- 1,1 C 0.00000000 1.85325000 0.07753100 C -0.49243700 3.17963400 0.14315700 C -0.39622700 4.08766600 -0.90836800 C 0.24454900 3.64821300 -2.06581400 C 0.78796200 2.35423300 -2.14309800 C 0.68233600 1.45528000 -1.08142700 C -0.24424600 1.25735000 1.39257400 C -0.82369600 2.28806800 2.17335400 C 0.00000000 0.00000000 1.96198300 N -0.99827900 3.38315300 1.43124900 H -0.78886600 5.09911800 -0.82025500 H 0.34269900 4.32455800 -2.91283800 H 1.30979700 2.04815400 -3.04796900 H 1.13725800 0.47370600 -1.15575000 H -1.14563400 2.24855800 3.21051800 H -1.42514300 4.25709000 1.76621800 H 0.00000000 0.00000000 3.05585600 C 0.24424600 -1.25735000 1.39257400 C 0.82369600 -2.28806800 2.17335400 H 1.14563400 -2.24855800 3.21051800 N 0.99827900 -3.38315300 1.43124900 H 1.42514300 -4.25709000 1.76621800 C 0.00000000 -1.85325000 0.07753100 C -0.68233600 -1.45528000 -1.08142700 C 0.49243700 -3.17963400 0.14315700 C -0.78796200 -2.35423300 -2.14309800 H -1.13725800 -0.47370600 -1.15575000 C 0.39622700 -4.08766600 -0.90836800 C -0.24454900 -3.64821300 -2.06581400 H -1.30979700 -2.04815400 -3.04796900 H 0.78886600 -5.09911800 -0.82025500 H -0.34269900 -4.32455800 -2.91283800 Total free energy in solution: with all non electrostatic terms -765.013787 Total non electrostatic (kcal/mol) = 3.07 Zero-point correction= 0.256581 Thermal correction to Energy= 0.270162 Thermal correction to Enthalpy= 0.271107 Thermal correction to Gibbs Free Energy= 0.216260 B2PLYP scrf(solvent=ethanol,externalIter) -764.172087 (this calculation was done with Gaussian 09) ---------------------------------------------------------- Urorosein Transition State between conformers 1 and 2 ---------------------------------------------------------- 1,1 C -2.32823500 0.12715000 -0.31827200 C -3.52406800 -0.55362300 0.04539900 C -4.72670500 0.12802900 0.27328400 C -4.71883400 1.51010100 0.12369800 C -3.54267000 2.20241100 -0.24182800 C -2.34907500 1.52687400 -0.46405900 C -1.30580300 -0.88735700 -0.45532600 C -1.90799000 -2.09861700 -0.18742300 C 0.08216900 -0.66776000 -0.88332600 N -3.23189100 -1.89869000 0.11372900 H -5.63125200 -0.40855900 0.55486400 H -5.63702700 2.07004300 0.29201300 H -3.57460200 3.28516700 -0.34976700 H -1.44797200 2.07088700 -0.74340500 H -1.48342100 -3.09628100 -0.19394000 H -3.88862500 -2.63894000 0.37200500 H 0.30473600 -0.72793600 -1.95462400 C 1.11167900 -0.36356600 -0.04898700 C 0.99810400 -0.25028200 1.39137500 H 0.11917800 -0.37801000 2.01770500 N 2.17349400 0.04344600 1.89440500 H 2.35705300 0.17423500 2.90509400 C 2.52724500 -0.09499600 -0.34844000 C 3.27991700 -0.04761000 -1.52020400 C 3.15878900 0.15396200 0.88363500 C 4.64414300 0.24722000 -1.41739700 H 2.82601200 -0.23393500 -2.49216100 C 4.50881100 0.44847600 1.01092100 C 5.24880600 0.49093600 -0.17523000 H 5.24872400 0.28835500 -2.32142600 H 4.96602200 0.63603900 1.98067900 H 6.31224800 0.71754700 -0.13090500 Total free energy in solution: with all non electrostatic terms -764.990903 Total non electrostatic (kcal/mol) = 3.47 Zero-point correction= 0.254931 Thermal correction to Energy= 0.268281 Thermal correction to Enthalpy= 0.269225 Thermal correction to Gibbs Free Energy= 0.214091 B2PLYP scrf(solvent=ethanol,externalIter) -764.150431 (this calculation was done with Gaussian 09) ---------------------------------------------------------- indole-3-carbinol (I3C) radical cation ---------------------------------------------------------- 1,2 C 0.00000000 0.41869800 0.00000000 C 1.22660200 -0.29940600 0.00000000 C 2.45756000 0.31658700 0.00000000 C 2.46051800 1.73209700 0.00000000 C 1.27213400 2.46911000 0.00000000 C 0.02855600 1.82717600 0.00000000 C -1.04861700 -0.54462300 0.00000000 C -0.41394400 -1.82808400 0.00000000 C -2.52185500 -0.33186900 0.00000000 N 0.90515400 -1.66885900 0.00000000 O -3.16498600 -1.58833900 0.00000000 H 3.38786700 -0.24936400 0.00000000 H 3.41680000 2.25255500 0.00000000 H 1.31494200 3.55628200 0.00000000 H -0.89342800 2.40711500 0.00000000 H -0.87829700 -2.80868400 0.00000000 H 1.59353000 -2.43993900 0.00000000 H -2.79223200 0.27570900 0.88293900 H -4.13887400 -1.43877300 0.00000000 H -2.79223200 0.27570900 -0.88293900 Total free energy in solution: with all non electrostatic terms -478.161302 Total non electrostatic (kcal/mol) = 6.04 Zero-point correction= 0.159522 Thermal correction to Energy= 0.168801 Thermal correction to Enthalpy= 0.169745 Thermal correction to Gibbs Free Energy= 0.123354 ---------------------------------------------------------- indole-3-carbinol ketyl radical (I3C-C.) ---------------------------------------------------------- 0,2 C 0.000000 0.377755 0.000000 C -1.188432 -0.404769 0.000000 C -2.461711 0.178838 0.000000 C -2.535470 1.569929 0.000000 C -1.370328 2.363328 0.000000 C -0.105595 1.776009 0.000000 C 1.129596 -0.550602 0.000000 C 0.560878 -1.835669 0.000000 C 2.487393 -0.207732 0.000000 N -0.819726 -1.732440 0.000000 O 3.430467 -1.204767 0.000000 H -3.360514 -0.436106 0.000000 H -3.512006 2.051844 0.000000 H -1.460808 3.448248 0.000000 H 0.787664 2.399911 0.000000 H 1.042399 -2.804812 0.000000 H -1.464457 -2.524095 0.000000 H 4.325358 -0.792834 0.000000 H 2.838715 0.820527 0.000000 Total free energy in solution: with all non electrostatic terms -477.712078 Total non electrostatic (kcal/mol) = 5.92 Zero-point correction= 0.146423 Thermal correction to Energy= 0.155642 Thermal correction to Enthalpy= 0.156586 Thermal correction to Gibbs Free Energy= 0.111845 ---------------------------------------------------------- indole-3-carbinol indolyl radical (I3C-N.) ---------------------------------------------------------- 0,2 C 0.00000000 0.40247800 0.00000000 C 1.23858600 -0.30501400 0.00000000 C 2.44711700 0.36766500 0.00000000 C 2.42121400 1.77974300 0.00000000 C 1.21319100 2.48255500 0.00000000 C -0.01532800 1.80141800 0.00000000 C -1.01127600 -0.61791600 0.00000000 C -0.28514100 -1.86032700 0.00000000 C -2.48909800 -0.44235700 0.00000000 N 1.02889800 -1.70481300 0.00000000 O -3.11838900 -1.71248600 0.00000000 H 3.39082100 -0.17560500 0.00000000 H 3.36178300 2.32834700 0.00000000 H 1.22309800 3.57095900 0.00000000 H -0.95092100 2.35976100 0.00000000 H -0.74039800 -2.84668000 0.00000000 H -2.78169000 0.15724600 0.88185600 H -4.09177200 -1.56715900 0.00000000 H -2.78169000 0.15724600 -0.88185600 Total free energy in solution: with all non electrostatic terms -477.698178 Total non electrostatic (kcal/mol) = 6.50 Zero-point correction= 0.147413 Thermal correction to Energy= 0.156421 Thermal correction to Enthalpy= 0.157365 Thermal correction to Gibbs Free Energy= 0.111984 ------------------------------------------------------- reactant complex (I3C radical cation + NH3 at CH-H) ------------------------------------------------------- 1,2 C -0.557227 0.123558 -0.277410 C -1.498680 -0.748359 0.329882 C -2.823615 -0.413595 0.516899 C -3.224151 0.863867 0.069551 C -2.321036 1.745994 -0.534518 C -0.980036 1.390094 -0.717613 C 0.699907 -0.560446 -0.293963 C 0.465447 -1.834354 0.311083 C 2.013167 -0.084360 -0.770198 N -0.813657 -1.929358 0.666488 O 2.887571 -1.181872 -0.978322 H -3.530284 -1.096851 0.985201 H -4.262952 1.163010 0.198369 H -2.667439 2.721538 -0.869498 H -0.284898 2.079690 -1.194506 H 1.172977 -2.639025 0.480959 H -1.240592 -2.752767 1.121474 H 1.881500 0.509067 -1.693450 H 3.800636 -0.886067 -0.759947 H 2.431458 0.630576 -0.014642 H 2.773931 2.702084 1.521817 N 3.414237 1.954251 1.239184 H 3.759990 1.537734 2.103050 H 4.218393 2.417339 0.805766 Total free energy in solution: with all non electrostatic terms -534.717790 Total non electrostatic (kcal/mol) = 8.71 Zero-point correction= 0.194743 Thermal correction to Energy= 0.207429 Thermal correction to Enthalpy= 0.208373 Thermal correction to Gibbs Free Energy= 0.152517 ------------------------------------------------------- reactant complex (I3C radical cation + NH3 at N-H) ------------------------------------------------------- 1,2 C -0.172811 -0.896209 0.015295 C 0.918921 0.014957 0.002204 C 2.233185 -0.399789 -0.018543 C 2.464934 -1.795400 -0.026623 C 1.411076 -2.714091 -0.015582 C 0.079951 -2.279898 0.004548 C -1.362127 -0.109653 0.036414 C -0.931087 1.257611 0.034278 C -2.778943 -0.561205 0.080652 N 0.392781 1.321579 0.013386 O -3.628008 0.545157 -0.151021 H 3.064340 0.303125 -0.028519 H 3.492180 -2.155629 -0.043299 H 1.627608 -3.780349 -0.023863 H -0.736129 -3.001347 0.010197 H -1.550373 2.149028 0.046248 H 0.971523 2.242691 0.006362 H -2.927413 -1.362816 -0.664824 H -4.551677 0.273468 0.057757 H -2.965645 -1.023947 1.067364 H 2.300625 3.826829 -0.881490 N 1.808590 3.663229 0.001269 H 1.194866 4.470449 0.143569 H 2.515979 3.705650 0.740229 Total free energy in solution: with all non electrostatic terms -534.728254 Total non electrostatic (kcal/mol) = 8.76 Zero-point correction= 0.196302 Thermal correction to Energy= 0.209000 Thermal correction to Enthalpy= 0.209944 Thermal correction to Gibbs Free Energy= 0.154978 --------------------------------------------------------- TS for proton transfer from CH-H to NH3 --------------------------------------------------------- 1,2 C 0.521266 -0.141456 -0.279458 C 1.409456 0.824201 0.256400 C 2.767427 0.581716 0.436937 C 3.240499 -0.681469 0.069093 C 2.379767 -1.657223 -0.462870 C 1.019725 -1.399810 -0.644339 C -0.789402 0.477668 -0.327991 C -0.628268 1.775499 0.198199 C -2.035570 -0.126294 -0.723611 N 0.663021 1.972056 0.529025 O -3.065694 0.786895 -0.942276 H 3.430825 1.341830 0.846004 H 4.297101 -0.910505 0.195887 H 2.782119 -2.629832 -0.740021 H 0.364703 -2.163538 -1.061393 H -1.372185 2.551708 0.338808 H 1.041694 2.845633 0.917621 H -1.945456 -0.900733 -1.505633 H -3.874630 0.284542 -1.206706 H -2.370069 -0.850767 0.254356 H -2.182432 -2.062248 1.976698 N -2.937957 -1.701254 1.386923 H -3.557535 -1.122802 1.961780 H -3.473430 -2.491058 1.015021 Total free energy in solution: with all non electrostatic terms -534.715509 Total non electrostatic (kcal/mol) = 8.17 Zero-point correction= 0.192514 Thermal correction to Energy= 0.204350 Thermal correction to Enthalpy= 0.205294 Thermal correction to Gibbs Free Energy= 0.151540 ------------------------------------------------------- TS for proton transfer from N-H to NH3 ------------------------------------------------------- 1,2 C 0.079781 -0.901529 0.003895 C -0.917159 0.114260 -0.006143 C -2.265132 -0.183948 -0.012016 C -2.628444 -1.550014 -0.009287 C -1.665083 -2.562734 0.001001 C -0.297986 -2.253111 0.008982 C 1.337712 -0.222641 0.004664 C 1.019393 1.177483 -0.004301 C 2.702396 -0.813042 0.016234 N -0.288529 1.379020 -0.010849 O 3.667477 0.221101 -0.015019 H -3.028295 0.592353 -0.023955 H -3.684846 -1.813238 -0.013627 H -1.979567 -3.604441 0.004922 H 0.446929 -3.047846 0.016455 H 1.725779 2.002177 -0.004432 H -0.856398 2.548417 -0.004848 H 2.808283 -1.447564 0.912848 H 4.559944 -0.194662 -0.007185 H 2.801115 -1.495146 -0.850835 H -1.734932 3.956611 0.963217 N -1.384684 3.718889 0.013280 H -0.691568 4.444204 -0.261304 H -2.186635 3.776607 -0.646287 Total free energy in solution: with all non electrostatic terms -534.726305 Total non electrostatic (kcal/mol) = 8.52 Zero-point correction= 0.192938 Thermal correction to Energy= 0.205245 Thermal correction to Enthalpy= 0.206190 Thermal correction to Gibbs Free Energy= 0.150897 ------------------------------------------------------- product complex (I3C-C. + NH4+) ------------------------------------------------------- 1,2 C -0.464171 0.082455 -0.371065 C -1.291569 -0.865146 0.290221 C -2.658938 -0.646930 0.493046 C -3.196667 0.548062 0.021337 C -2.393592 1.501516 -0.637263 C -1.032872 1.277694 -0.836985 C 0.884016 -0.477690 -0.403459 C 0.794566 -1.722424 0.235767 C 2.040160 0.137470 -0.933998 N -0.500872 -1.940858 0.643604 O 3.200029 -0.593064 -0.985811 H -3.276511 -1.385862 1.001295 H -4.257506 0.748101 0.163360 H -2.845044 2.425122 -0.995385 H -0.424105 2.022374 -1.348910 H 1.566811 -2.458377 0.421352 H -0.827638 -2.781500 1.125683 H 3.899549 -0.049666 -1.421678 H 1.978618 1.025235 -1.564095 N 2.363585 1.797858 1.713681 H 3.179813 1.403132 2.210836 H 2.547442 2.792219 1.498134 H 2.202293 1.264610 0.825990 H 1.531459 1.730075 2.323315 Total free energy in solution: with all non electrostatic terms -534.731250 Total non electrostatic (kcal/mol) = 8.69 Zero-point correction= 0.196430 Thermal correction to Energy= 0.208631 Thermal correction to Enthalpy= 0.209575 Thermal correction to Gibbs Free Energy= 0.156565 ------------------------------------------------------- product complex (I3C-N. + NH4+) ------------------------------------------------------- 1,2 C 0.244280 -0.908117 0.011432 C -0.907444 -0.069327 -0.003287 C -2.184324 -0.597546 -0.019599 C -2.315019 -2.004388 -0.021316 C -1.194427 -2.839583 -0.007791 C 0.101428 -2.301817 0.008445 C 1.366946 -0.018620 0.025478 C 0.800726 1.303249 0.017717 C 2.812795 -0.365648 0.067011 N -0.521925 1.291985 0.000533 O 3.590345 0.804783 -0.115647 H -3.065812 0.041648 -0.031112 H -3.311629 -2.442551 -0.034248 H -1.327455 -3.919709 -0.010237 H 0.969729 -2.959841 0.017484 H 1.364294 2.231680 0.024153 H -1.485974 2.703673 0.000902 H 3.031635 -0.852033 1.035746 H 4.532828 0.571217 0.045939 H 3.026452 -1.125029 -0.706991 H -2.453249 3.780700 0.949292 N -2.058648 3.617132 0.010244 H -1.456996 4.417192 -0.239694 H -2.832345 3.561762 -0.670042 Total free energy in solution: with all non electrostatic terms -534.729866 Total non electrostatic (kcal/mol) = 8.89 Zero-point correction= 0.197347 Thermal correction to Energy= 0.210035 Thermal correction to Enthalpy= 0.210980 Thermal correction to Gibbs Free Energy= 0.155470 ========================================================== Results from TD-DFT calculations (for results of CASSCF/CASPT2 calculations, see .doc file) ========================================================== ------------------------------------------------------- indole radical cation ------------------------------------------------------- Excited State 1: ?Spin -A' 1.0047 eV 1234.00 nm f=0.0004 27A -> 32A 0.10651 30B -> 31B 1.03716 Excited State 2: ?Spin -A' 2.3653 eV 524.19 nm f=0.0547 30A -> 32A -0.15536 31A -> 32A -0.20297 29B -> 31B 0.94690 Excited State 3: ?Spin -A' 3.4979 eV 354.46 nm f=0.0072 29A -> 33A 0.10133 30A -> 32A -0.57153 31A -> 32A 0.18023 31A -> 33A -0.13700 28B -> 31B 0.82442 30B -> 32B 0.25424 Excited State 4: ?Spin -A" 3.9534 eV 313.62 nm f=0.0000 27B -> 31B 0.99594 Excited State 5: ?Spin -A' 4.0579 eV 305.54 nm f=0.0897 30A -> 33A 0.39016 31A -> 32A 0.86722 28B -> 31B -0.18060 29B -> 32B 0.20900 29B -> 34B 0.18513 30B -> 33B -0.17398 Excited State 6: ?Spin -A" 4.3327 eV 286.16 nm f=0.0000 26B -> 31B 0.99301 Excited State 7: ?Spin -A' 4.4093 eV 281.19 nm f=0.0189 30A -> 32A 0.59197 30A -> 33A -0.18457 31A -> 32A 0.17058 31A -> 33A -0.14194 31A -> 34A -0.10281 28B -> 31B 0.46493 30B -> 32B -0.59110 30B -> 33B 0.16930 Excited State 8: ?Spin -A' 4.8990 eV 253.08 nm f=0.0171 29A -> 32A 0.30533 30A -> 32A -0.28375 30A -> 33A -0.54181 31A -> 32A 0.29322 31A -> 33A 0.22599 31A -> 34A -0.15819 23B -> 31B 0.20218 28B -> 31B -0.14746 29B -> 32B -0.28496 30B -> 33B 0.57005 Excited State 9: ?Spin -A' 5.1362 eV 241.39 nm f=0.0135 30A -> 32A -0.29205 30A -> 33A 0.21345 31A -> 33A 0.68491 30B -> 32B -0.54912 30B -> 33B -0.29878 Excited State 10: ?Spin -A' 5.3636 eV 231.16 nm f=0.0069 29A -> 32A -0.41444 30A -> 32A -0.10989 30A -> 33A -0.30556 31A -> 34A 0.47674 29B -> 32B 0.64360 30B -> 32B -0.22476 30B -> 33B 0.27144 Excited State 11: ?Spin -A" 5.4091 eV 229.21 nm f=0.0000 24B -> 31B 0.10687 25B -> 31B 0.98894 Excited State 12: ?Spin -A" 5.8135 eV 213.27 nm f=0.0003 24B -> 31B 0.98680 25B -> 31B -0.10287 ------------------------------------------------------- indole radical ------------------------------------------------------- Excited State 1: ?Spin -A' 1.2550 eV 987.93 nm f=0.0001 30A -> 32A -0.10896 30B -> 31B 1.03374 Excited State 2: ?Spin -A" 1.9374 eV 639.95 nm f=0.0004 29B -> 31B 1.00484 Excited State 3: ?Spin -A' 2.6832 eV 462.07 nm f=0.0376 30A -> 32A 0.15268 31A -> 32A 0.19350 31A -> 33A 0.16727 28B -> 31B 0.96160 30B -> 32B 0.10800 Excited State 4: ?Spin -A' 3.7717 eV 328.72 nm f=0.0050 28A -> 34A -0.11551 30A -> 32A 0.58486 31A -> 32A -0.37762 27B -> 31B 0.68227 28B -> 32B 0.17654 30B -> 32B -0.33716 Excited State 5: ?Spin -A' 4.0847 eV 303.54 nm f=0.0189 28A -> 32A -0.18514 30A -> 32A -0.25546 30A -> 33A 0.46527 30A -> 34A 0.13045 31A -> 32A 0.47665 31A -> 33A 0.21284 31A -> 34A -0.13380 23B -> 31B -0.10658 27B -> 31B 0.53124 27B -> 33B 0.11580 28B -> 32B -0.38932 30B -> 32B 0.15981 30B -> 33B 0.23565 Excited State 6: ?Spin -A' 4.1513 eV 298.67 nm f=0.0143 30A -> 32A 0.48480 31A -> 32A 0.65725 31A -> 33A -0.13591 27B -> 31B -0.23290 30B -> 32B -0.56204 Excited State 7: ?Spin -A" 4.6075 eV 269.09 nm f=0.0000 26B -> 31B 0.98655 Excited State 8: ?Spin -A' 5.0367 eV 246.16 nm f=0.0085 28A -> 33A -0.10793 30A -> 32A -0.28152 31A -> 32A -0.14370 31A -> 33A 0.72616 27B -> 31B -0.15973 30B -> 32B -0.54163 30B -> 33B 0.20094 Excited State 9: ?Spin -A" 5.0728 eV 244.41 nm f=0.0000 25B -> 31B 0.98847 Excited State 10: ?Spin -A' 5.0820 eV 243.97 nm f=0.0178 28A -> 32A -0.26257 30A -> 32A 0.24811 30A -> 33A 0.51872 31A -> 32A -0.26148 31A -> 33A -0.14585 23B -> 31B -0.17373 27B -> 31B -0.35474 28B -> 32B -0.10042 30B -> 33B 0.60122 Excited State 11: ?Spin -A' 5.2888 eV 234.43 nm f=0.0073 28A -> 32A 0.45437 30A -> 33A 0.41205 30A -> 34A -0.22833 31A -> 32A 0.15380 31A -> 34A 0.30690 23B -> 31B 0.44832 28B -> 32B 0.51931 30B -> 32B 0.11610 30B -> 33B 0.20257 Excited State 12: ?Spin -A" 5.4503 eV 227.48 nm f=0.0001 29A -> 32A 0.83579 29A -> 34A 0.19015 24B -> 31B 0.34415 29B -> 32B -0.34021 29B -> 34B -0.12266 ------------------------------------------------------- indole-3-carbinol radical cation ------------------------------------------------------- Excited State 1: ?Spin -A' 1.1036 eV 1123.40 nm f=0.0004 37B -> 39B 0.15824 38B -> 39B 1.01628 Excited State 2: ?Spin -A' 1.7865 eV 694.02 nm f=0.0281 37B -> 39B 0.96578 38B -> 39B -0.14361 Excited State 3: ?Spin -A' 2.4333 eV 509.53 nm f=0.0384 38A -> 40A -0.15149 39A -> 40A 0.15368 39A -> 41A 0.10213 36B -> 39B 0.96245 Excited State 4: ?Spin -A" 3.6219 eV 342.32 nm f=0.0003 33B -> 39B 0.15764 35B -> 39B 0.98413 Excited State 5: ?Spin -A' 3.6339 eV 341.19 nm f=0.0055 37A -> 40A -0.28261 38A -> 40A 0.47838 39A -> 40A 0.33604 39A -> 41A -0.11125 34B -> 39B 0.76393 37B -> 40B 0.16312 38B -> 40B 0.24448 Excited State 6: ?Spin -A' 4.0028 eV 309.74 nm f=0.0684 37A -> 41A 0.14453 38A -> 40A -0.19027 38A -> 41A -0.36821 39A -> 40A 0.79553 34B -> 39B -0.28942 36B -> 40B -0.21394 36B -> 42B -0.15680 37B -> 40B 0.15549 38B -> 40B -0.13448 38B -> 41B -0.17477 Excited State 7: ?Spin -A" 4.1919 eV 295.77 nm f=0.0002 32B -> 39B 0.13974 33B -> 39B 0.97471 35B -> 39B -0.15295 Excited State 8: ?Spin -A' 4.4174 eV 280.67 nm f=0.0160 37A -> 40A -0.19656 38A -> 40A 0.53357 38A -> 41A -0.23797 39A -> 40A -0.16638 39A -> 41A 0.10069 34B -> 39B -0.48345 37B -> 40B 0.20856 38B -> 40B 0.54463 38B -> 41B -0.19151 Excited State 9: ?Spin -A" 4.4807 eV 276.71 nm f=0.0000 32B -> 39B 0.98401 33B -> 39B -0.14266 Excited State 10: ?Spin -A' 4.7434 eV 261.38 nm f=0.0243 36A -> 40A 0.28732 37A -> 40A 0.32258 37A -> 41A -0.17535 38A -> 40A 0.42899 38A -> 41A 0.30860 39A -> 40A 0.37410 39A -> 41A 0.24056 39A -> 42A -0.17414 29B -> 39B 0.15745 34B -> 39B -0.16824 36B -> 40B 0.25949 37B -> 40B -0.22455 38B -> 41B 0.40413 Excited State 11: ?Spin -A' 5.0784 eV 244.14 nm f=0.0128 37A -> 40A -0.34188 38A -> 40A -0.29162 38A -> 41A 0.42590 39A -> 41A -0.42668 34B -> 39B -0.17261 37B -> 40B 0.17216 37B -> 41B 0.12120 38B -> 40B 0.38530 38B -> 41B 0.48066 Excited State 12: ?Spin -A' 5.1405 eV 241.19 nm f=0.0014 37A -> 40A 0.59776 37A -> 41A 0.18466 38A -> 41A -0.15697 39A -> 41A -0.54749 39A -> 42A -0.15012 36B -> 40B 0.15951 37B -> 40B -0.12790 38B -> 40B 0.40887 38B -> 41B -0.17444 ------------------------------------------------------- indole-3-carbinol indolyl radical ------------------------------------------------------- Excited State 1: ?Spin -A' 1.3601 eV 911.61 nm f=0.0002 38A -> 40A -0.10466 38B -> 39B 1.02910 Excited State 2: ?Spin -A" 1.9904 eV 622.91 nm f=0.0005 37B -> 39B 1.00419 Excited State 3: ?Spin -A' 2.7164 eV 456.42 nm f=0.0432 38A -> 40A 0.15997 39A -> 40A 0.16515 39A -> 41A 0.17108 36B -> 39B 0.96158 Excited State 4: ?Spin -A' 3.5552 eV 348.74 nm f=0.0101 39A -> 40A 0.12528 35B -> 39B 0.97799 Excited State 5: ?Spin -A' 3.8027 eV 326.05 nm f=0.0033 36A -> 40A -0.14428 38A -> 40A -0.55657 39A -> 40A 0.56037 34B -> 39B -0.51400 35B -> 39B -0.14406 36B -> 40B -0.26496 38B -> 40B 0.34345 Excited State 6: ?Spin -A' 4.0681 eV 304.77 nm f=0.0216 36A -> 40A -0.12865 38A -> 40A 0.11588 38A -> 41A 0.45648 38A -> 43A 0.14552 39A -> 40A 0.54457 39A -> 41A 0.12937 39A -> 43A -0.12860 34B -> 39B 0.57068 36B -> 40B -0.33040 38B -> 40B -0.14643 38B -> 41B 0.20233 Excited State 7: ?Spin -A' 4.1150 eV 301.30 nm f=0.0048 38A -> 40A -0.54387 38A -> 41A 0.16967 39A -> 40A -0.44533 39A -> 41A 0.19290 34B -> 39B 0.40733 38B -> 40B 0.56830 38B -> 41B 0.16880 Excited State 8: ?Spin -A" 4.5692 eV 271.35 nm f=0.0001 33B -> 39B 0.98549 Excited State 9: ?Spin -A' 4.9539 eV 250.28 nm f=0.0035 36A -> 41A -0.11859 38A -> 40A -0.29601 39A -> 41A 0.77430 34B -> 39B -0.11692 38B -> 40B -0.50578 Excited State 10: ?Spin -A' 5.0251 eV 246.73 nm f=0.0207 35A -> 40A 0.16782 36A -> 40A -0.28075 38A -> 40A 0.20528 38A -> 41A 0.45528 39A -> 40A -0.29036 29B -> 39B -0.14005 34B -> 39B -0.41135 36B -> 40B -0.17744 38B -> 41B 0.58921 Excited State 11: ?Spin -A" 5.1632 eV 240.13 nm f=0.0001 30B -> 39B -0.15207 32B -> 39B 0.97000 Excited State 12: ?Spin -A' 5.2194 eV 237.55 nm f=0.0027 35A -> 40A -0.25265 36A -> 40A 0.42354 38A -> 41A 0.46184 38A -> 43A -0.11325 39A -> 40A 0.14850 39A -> 43A 0.28985 29B -> 39B 0.32315 35B -> 40B 0.10887 36B -> 40B 0.55056 38B -> 41B 0.26854 ------------------------------------------------------- indole-3-carbinol ketyl radical ------------------------------------------------------- Excited State 1: ?Spin -A' 2.4907 eV 497.79 nm f=0.0073 39A -> 40A 0.96079 38B -> 39B -0.35258 Excited State 2: ?Spin -A' 3.4155 eV 363.01 nm f=0.0135 37A -> 41A 0.18729 38A -> 40A 0.21178 39A -> 41A 0.85319 39A -> 45A -0.11834 36B -> 40B 0.12410 37B -> 39B -0.21230 37B -> 40B 0.18383 37B -> 41B -0.21252 38B -> 39B -0.31645 38B -> 40B -0.12371 Excited State 3: ?Spin -A' 3.7515 eV 330.49 nm f=0.0116 36A -> 40A 0.20214 37A -> 40A 0.21677 37A -> 41A -0.25015 38A -> 40A -0.51750 39A -> 41A 0.37386 36B -> 40B -0.22100 37B -> 39B 0.31458 37B -> 40B -0.22257 37B -> 41B 0.19091 38B -> 40B 0.60813 38B -> 41B 0.16922 Excited State 4: ?Spin -A' 3.8444 eV 322.50 nm f=0.0307 37A -> 40A 0.14879 38A -> 40A 0.18300 39A -> 40A 0.22807 39A -> 41A 0.31105 39A -> 45A 0.34407 37B -> 40B -0.13544 37B -> 41B -0.13546 38B -> 39B 0.79682 Excited State 5: ?Spin -A" 3.9739 eV 312.00 nm f=0.0001 39A -> 42A 0.99180 Excited State 6: ?Spin -A' 4.0902 eV 303.13 nm f=0.0447 37A -> 40A 0.18923 38A -> 40A 0.39528 39A -> 45A -0.14154 37B -> 39B 0.83975 38B -> 39B -0.10898 38B -> 40B -0.27941 Excited State 7: ?Spin -A' 4.3493 eV 285.06 nm f=0.0027 37A -> 40A 0.64905 38A -> 41A 0.12107 36B -> 39B 0.12155 37B -> 39B -0.28067 37B -> 40B -0.64130 38B -> 39B -0.20850 38B -> 40B -0.20798 38B -> 41B -0.15326 Excited State 8: ?Spin -A" 4.7685 eV 260.01 nm f=0.0001 39A -> 43A 0.99287 Excited State 9: ?Spin -A' 4.7736 eV 259.73 nm f=0.0028 37A -> 40A 0.12238 37A -> 41A 0.57921 38A -> 40A -0.11215 38A -> 41A 0.28377 39A -> 45A 0.13420 36B -> 39B 0.10031 37B -> 39B 0.16941 37B -> 40B 0.12281 37B -> 41B -0.47200 38B -> 40B 0.34181 38B -> 41B -0.47674 Excited State 10: ?Spin -A' 5.0979 eV 243.21 nm f=0.0159 37A -> 40A 0.18937 37A -> 41A -0.28857 38A -> 40A 0.24521 39A -> 45A 0.25814 36B -> 39B 0.36996 36B -> 41B 0.10149 37B -> 40B 0.41953 37B -> 41B 0.48741 38B -> 40B 0.15125 38B -> 41B -0.44037 Excited State 11: ?Spin -A' 5.2626 eV 235.59 nm f=0.0361 36A -> 41A -0.13905 37A -> 40A -0.54857 37A -> 41A -0.18244 38A -> 41A 0.65364 39A -> 45A 0.20653 36B -> 39B 0.11115 37B -> 40B -0.36815 37B -> 41B 0.11010 38B -> 41B -0.11363 Excited State 12: ?Spin -A' 5.3908 eV 229.99 nm f=0.1411 37A -> 41A 0.19735 38A -> 40A 0.56397 39A -> 45A -0.16772 36B -> 39B -0.25486 36B -> 40B 0.20291 37B -> 39B -0.10764 37B -> 40B -0.23817 37B -> 41B 0.20906 38B -> 40B 0.54472 ------------------------------------------------------- Diindolylmethane C-radical C2 symmetry (conformer 1) ------------------------------------------------------- Excited State 1: ?Spin -B 2.3703 eV 523.07 nm f=0.0001 64A -> 67A -0.12815 65A -> 66A 0.82875 65A -> 70A -0.14016 64B -> 65B -0.60705 Excited State 2: ?Spin -A 2.7886 eV 444.62 nm f=0.0044 64A -> 66A -0.18403 65A -> 67A 0.94232 59B -> 65B -0.10035 61B -> 65B 0.20328 63B -> 65B 0.18167 64B -> 66B 0.20664 Excited State 3: ?Spin -B 3.1180 eV 397.65 nm f=0.2672 65A -> 66A 0.51969 65A -> 69A -0.16656 65A -> 70A 0.16931 64B -> 65B 0.73820 Excited State 4: ?Spin -A 3.4442 eV 359.98 nm f=0.0012 60A -> 66A -0.12314 61A -> 67A 0.21410 62A -> 68A -0.14288 63A -> 69A 0.15065 64A -> 66A 0.19571 65A -> 68A 0.33841 60B -> 66B 0.11895 61B -> 67B 0.23572 62B -> 66B 0.13400 62B -> 69B -0.14618 63B -> 65B 0.80476 63B -> 68B 0.12874 64B -> 66B -0.24513 Excited State 5: ?Spin -B 3.4729 eV 357.01 nm f=0.0577 60A -> 67A 0.12800 61A -> 66A -0.20961 62A -> 69A 0.12755 63A -> 68A -0.13851 64A -> 67A -0.19949 65A -> 69A -0.23337 60B -> 67B -0.11704 61B -> 66B -0.22971 62B -> 65B 0.83338 62B -> 68B 0.14166 63B -> 69B -0.14954 64B -> 65B -0.13758 64B -> 67B 0.24764 Excited State 6: ?Spin -A 3.6179 eV 342.70 nm f=0.0035 61A -> 67A 0.29140 62A -> 67A -0.12939 62A -> 68A -0.10986 63A -> 66A 0.12781 63A -> 69A 0.12025 64A -> 66A 0.57385 65A -> 67A 0.29595 60B -> 66B 0.11363 61B -> 67B 0.27997 62B -> 69B -0.13999 63B -> 65B -0.40915 63B -> 67B 0.11659 63B -> 68B 0.13770 64B -> 66B -0.48826 Excited State 7: ?Spin -B 3.7206 eV 333.24 nm f=0.0093 60A -> 67A -0.14270 61A -> 66A 0.30249 62A -> 66A -0.15573 62A -> 69A -0.11951 63A -> 68A 0.13047 64A -> 67A 0.42231 65A -> 66A 0.15590 65A -> 69A 0.40349 60B -> 67B 0.15158 61B -> 66B 0.27876 62B -> 65B 0.50483 62B -> 68B -0.17279 63B -> 69B 0.15021 64B -> 67B -0.37038 Excited State 8: ?Spin -A 3.7573 eV 329.98 nm f=0.0132 64A -> 69A -0.10280 65A -> 68A 0.89687 61B -> 65B 0.10242 63B -> 65B -0.30587 64B -> 66B 0.20629 64B -> 69B 0.12538 Excited State 9: ?Spin -B 3.8066 eV 325.71 nm f=0.0021 61A -> 66A -0.18706 64A -> 67A -0.25387 65A -> 69A 0.83130 61B -> 66B -0.20467 63B -> 66B -0.10734 64B -> 65B 0.10935 64B -> 67B 0.36241 64B -> 68B 0.10361 Excited State 10: ?Spin -A 3.9039 eV 317.59 nm f=0.0016 65A -> 67A -0.13107 65A -> 68A -0.11121 65A -> 77A -0.14793 61B -> 65B 0.94139 64B -> 66B -0.10147 ------------------------------------------------------- Diindolylmethane C-radical C1 symmetry (conformer 2) ------------------------------------------------------- Excited State 1: ?Spin -A 2.3346 eV 531.07 nm f=0.0057 64A -> 67A -0.11710 65A -> 66A 0.90228 65A -> 70A -0.12187 64B -> 65B -0.47356 64B -> 67B 0.10924 Excited State 2: ?Spin -A 2.7037 eV 458.57 nm f=0.0017 64A -> 66A -0.17451 65A -> 67A 0.94508 61B -> 65B 0.16802 63B -> 65B -0.12808 64B -> 65B 0.11346 64B -> 66B 0.19763 Excited State 3: ?Spin -A 3.1540 eV 393.11 nm f=0.2227 65A -> 66A 0.37535 65A -> 67A -0.12279 65A -> 68A -0.12833 65A -> 69A 0.13770 65A -> 70A 0.21449 64B -> 65B 0.81503 Excited State 4: ?Spin -A 3.4725 eV 357.05 nm f=0.0082 60A -> 66A -0.12583 61A -> 67A -0.23952 62A -> 68A 0.11575 63A -> 69A -0.19099 64A -> 66A -0.23294 65A -> 68A -0.27577 65A -> 69A -0.32495 60B -> 66B 0.12057 61B -> 67B -0.25279 62B -> 65B -0.20777 62B -> 68B -0.10853 63B -> 65B 0.68866 63B -> 69B 0.18677 64B -> 66B 0.24109 64B -> 67B -0.12036 Excited State 5: ?Spin -A 3.5218 eV 352.05 nm f=0.0186 60A -> 67A 0.13439 61A -> 66A 0.26317 62A -> 68A -0.20605 64A -> 66A 0.21845 64A -> 67A 0.24409 65A -> 68A 0.34337 65A -> 69A -0.20113 60B -> 67B -0.12287 61B -> 66B 0.28839 62B -> 65B 0.55287 62B -> 68B 0.21616 63B -> 65B 0.31285 63B -> 69B 0.10688 64B -> 65B 0.13136 64B -> 66B -0.22054 64B -> 67B -0.24002 Excited State 6: ?Spin -A 3.6051 eV 343.91 nm f=0.0033 61A -> 67A -0.21190 64A -> 66A -0.45443 65A -> 67A -0.21439 65A -> 68A 0.61236 61B -> 66B -0.10156 61B -> 67B -0.20741 62B -> 65B 0.16668 63B -> 65B -0.10938 64B -> 66B 0.46891 Excited State 7: ?Spin -A 3.6886 eV 336.13 nm f=0.0061 61A -> 67A 0.12599 62A -> 66A -0.12442 64A -> 66A 0.26157 64A -> 67A -0.17052 65A -> 67A 0.16367 65A -> 68A 0.59203 61B -> 66B -0.10294 61B -> 67B 0.11459 62B -> 65B -0.49089 63B -> 65B 0.35487 63B -> 69B -0.10254 64B -> 66B -0.11572 64B -> 67B 0.21848 Excited State 8: ?Spin -A 3.7302 eV 332.38 nm f=0.0282 65A -> 68A -0.10485 65A -> 69A 0.83141 62B -> 65B 0.21292 63B -> 65B 0.41780 64B -> 69B -0.11190 Excited State 9: ?Spin -A 3.7791 eV 328.08 nm f=0.0039 60A -> 67A -0.13202 61A -> 66A -0.30047 61A -> 67A 0.10066 63A -> 69A 0.12472 64A -> 67A -0.43521 65A -> 66A -0.13527 65A -> 69A -0.28026 60B -> 67B 0.13783 61B -> 66B -0.26775 61B -> 67B 0.13084 62B -> 65B 0.50368 63B -> 65B 0.18974 63B -> 69B -0.12367 64B -> 67B 0.43716 Excited State 10: ?Spin -A 3.9353 eV 315.05 nm f=0.0065 62A -> 66A -0.10288 65A -> 67A -0.10866 65A -> 75A 0.15705 61B -> 65B 0.94214 62B -> 65B -0.10428 ------------------------------------------------------- Diindolylmethane C-radical C2 symmetry (conformer 3) ------------------------------------------------------- Excited State 1: ?Spin -B 2.3298 eV 532.17 nm f=0.0099 64A -> 67A 0.12367 65A -> 66A 0.91393 65A -> 70A 0.11413 61B -> 66B 0.10588 64B -> 65B -0.45169 64B -> 67B 0.12076 Excited State 2: ?Spin -A 2.7916 eV 444.14 nm f=0.0030 64A -> 66A 0.20028 65A -> 67A 0.92998 59B -> 65B 0.10339 61B -> 65B 0.19753 61B -> 67B -0.10576 63B -> 65B -0.20766 64B -> 66B -0.23456 Excited State 3: ?Spin -B 3.1898 eV 388.69 nm f=0.1987 65A -> 66A 0.35618 65A -> 68A -0.24734 65A -> 70A -0.23821 64B -> 65B 0.81705 Excited State 4: ?Spin -A 3.4921 eV 355.05 nm f=0.0001 60A -> 66A 0.15002 61A -> 67A -0.25904 62A -> 68A -0.17338 63A -> 69A -0.16007 64A -> 66A 0.29344 65A -> 69A 0.28741 60B -> 66B -0.14769 61B -> 67B -0.27921 61B -> 69B 0.10110 62B -> 66B 0.16264 62B -> 68B -0.16228 63B -> 65B 0.72778 63B -> 69B 0.12989 64B -> 66B -0.31693 Excited State 5: ?Spin -B 3.5262 eV 351.61 nm f=0.0293 60A -> 67A 0.12325 61A -> 66A -0.26596 62A -> 69A 0.13625 63A -> 68A 0.14789 64A -> 67A 0.19036 65A -> 68A -0.42172 60B -> 67B 0.12430 61B -> 66B 0.27954 62B -> 65B 0.71553 62B -> 69B 0.16335 63B -> 68B -0.16222 64B -> 65B -0.18871 64B -> 67B 0.20095 Excited State 6: ?Spin -A 3.6685 eV 337.97 nm f=0.0017 61A -> 67A 0.20976 62A -> 66A 0.12196 63A -> 67A -0.10943 64A -> 66A -0.50546 65A -> 67A 0.35173 61B -> 65B -0.24559 61B -> 67B 0.18288 62B -> 68B 0.11945 63B -> 65B 0.52871 63B -> 67B -0.13212 64B -> 66B 0.39591 Excited State 7: ?Spin -B 3.6868 eV 336.29 nm f=0.0065 61A -> 66A -0.12453 64A -> 67A 0.12877 65A -> 68A 0.84598 61B -> 66B 0.15347 62B -> 65B 0.35411 64B -> 65B 0.14013 64B -> 67B 0.23206 Excited State 8: ?Spin -B 3.7938 eV 326.81 nm f=0.0020 60A -> 67A -0.14474 61A -> 66A 0.38532 62A -> 67A 0.13301 62A -> 69A -0.10851 63A -> 66A -0.15992 63A -> 68A -0.13082 64A -> 67A -0.40926 65A -> 66A 0.15160 60B -> 67B -0.15300 61B -> 66B -0.35982 62B -> 65B 0.54469 62B -> 69B -0.14097 63B -> 66B 0.16888 63B -> 68B 0.14878 64B -> 67B -0.39061 Excited State 9: ?Spin -A 3.7963 eV 326.59 nm f=0.0005 61A -> 67A 0.14492 64A -> 66A -0.15269 65A -> 69A 0.52554 61B -> 65B 0.75538 61B -> 67B 0.13315 64B -> 66B 0.22963 Excited State 10: ?Spin -A 3.8379 eV 323.05 nm f=0.0303 65A -> 69A 0.75083 61B -> 65B -0.52430 63B -> 65B -0.28530 64B -> 66B 0.12235 64B -> 68B 0.11275 ------------------------------------------------------- Urorosein C2 symmetry (conformer 1) ------------------------------------------------------- Excited State 1: Singlet-B 2.5895 eV 478.79 nm f=0.4297 60 -> 65 -0.14536 64 -> 65 0.60884 Excited State 2: Singlet-A 2.7905 eV 444.30 nm f=0.0140 61 -> 65 0.10469 63 -> 65 0.67231 Excited State 3: Singlet-B 2.7911 eV 444.21 nm f=0.0639 62 -> 65 0.67976 Excited State 4: Singlet-A 3.0997 eV 399.99 nm f=0.0018 61 -> 65 0.66587 Excited State 5: Singlet-B 4.2484 eV 291.83 nm f=0.3408 60 -> 65 0.65070 63 -> 66 0.11086 Excited State 6: Singlet-A 4.7532 eV 260.84 nm f=0.0767 64 -> 66 0.65596 Excited State 7: Singlet-B 5.0342 eV 246.28 nm f=0.0031 63 -> 66 -0.33132 64 -> 67 0.56297 64 -> 68 0.15663 Excited State 8: Singlet-A 5.1501 eV 240.74 nm f=0.0173 61 -> 68 -0.17263 62 -> 66 0.53719 63 -> 67 0.19601 64 -> 69 -0.33636 Excited State 9: Singlet-B 5.1806 eV 239.32 nm f=0.1183 61 -> 66 -0.12551 61 -> 69 -0.13752 62 -> 67 0.19758 63 -> 66 0.42700 64 -> 67 0.35070 64 -> 68 -0.29988 Excited State 10: Singlet-A 5.3492 eV 231.78 nm f=0.0077 56 -> 65 -0.23833 59 -> 65 0.63982 ------------------------------------------------------- Urorosein C1 symmetry (conformer 2) ------------------------------------------------------- Excited State 1: Singlet-A 2.7471 eV 451.32 nm f=0.4091 60 -> 65 -0.14004 62 -> 65 0.13655 64 -> 65 0.59982 Excited State 2: Singlet-A 2.8972 eV 427.95 nm f=0.0697 63 -> 65 0.67335 Excited State 3: Singlet-A 3.0053 eV 412.55 nm f=0.0173 62 -> 65 0.66788 64 -> 65 -0.10381 Excited State 4: Singlet-A 3.2832 eV 377.63 nm f=0.0134 61 -> 65 0.66831 Excited State 5: Singlet-A 4.3784 eV 283.17 nm f=0.3235 60 -> 65 0.63888 62 -> 66 -0.10925 Excited State 6: Singlet-A 4.7237 eV 262.47 nm f=0.0642 64 -> 66 0.66079 Excited State 7: Singlet-A 5.0184 eV 247.06 nm f=0.0249 61 -> 66 0.10034 62 -> 66 0.15388 63 -> 66 0.24214 64 -> 67 0.58511 64 -> 69 0.10321 Excited State 8: Singlet-A 5.1501 eV 240.74 nm f=0.0078 61 -> 68 -0.13863 61 -> 69 -0.10872 62 -> 66 0.39740 62 -> 67 0.10535 63 -> 66 -0.34834 63 -> 67 0.18717 64 -> 68 0.28641 64 -> 69 -0.20774 Excited State 9: Singlet-A 5.1918 eV 238.81 nm f=0.1395 61 -> 66 -0.10057 61 -> 68 -0.13097 62 -> 66 0.30584 62 -> 67 0.11413 63 -> 66 0.32089 63 -> 67 -0.17125 64 -> 67 -0.28513 64 -> 68 0.24015 64 -> 69 0.23312 Excited State 10: Singlet-A 5.3930 eV 229.90 nm f=0.0011 63 -> 66 0.41665 63 -> 67 0.51955 64 -> 69 -0.20277 ------