Prediction of the Thermodynamic Properties of Key Products and Intermediates from

Biomass

Monica Vasiliu, Kurt Guynn and David A. Dixon*,1

Chemistry Department, The University of Alabama, Shelby Hall, Box 870336, Tuscaloosa,

Alabama 35487-0336

Supporting Information Thermochemical Values at the G3MP2 Level of Theory Given in

Hartrees. Water Solvation Energy Contributions in kcal/mol. Optimized B3LYP/DZVP2

Cartesian Coordinates in Angstroms for the Various Structures.

1
Email: dadixon@bama.ua.edu

1
Table S1. Thermochemical Values at the G3MP2 Level of Theory Given in Hartrees.

Compound E H298K G298K

acrylic acid -266.802388 -266.796329 -266.830478
BH-HMF -574.931008 -574.916848 -574.972759
C9H18O3 -578.529636 -578.514508 -578.571803
C9H18O -428.243384 -428.230377 -428.282716
DFF -456.043846 -456.035167 -456.076771
DHMF -458.424947 -458.414623 -458.460090
DHM-THF -460.818697 -460.807750 -460.854340
epichlorohydrin -651.954006 -651.947786 -651.983254
glucose -686.275656 -686.261921 -686.313622
glyceraldehyde -343.121580 -343.113911 -343.151952
glycerin -344.314549 -344.306168 -344.345522
glycerin carbonate -456.334628 -456.326100 -456.367317
HMF -457.239755 -457.230338 -457.273626
lactic acid -343.154424 -343.146481 -343.185697
methanol -115.552220 -115.547929 -115.574947
nonane -354.290895 -354.277098 -354.330088
propanediol -269.174078 -269.166645 -269.203308
propylene -117.672793 -117.667683 -117.697861
sorbitol -687.463791 -687.448483 -687.504811
1,3-propandiol -269.162976 -269.155270 -269.192383
3-hydroxypropanal -192.809491 -192.803408 -192.836813
succinonitrile -263.901978 -263.894780 -263.931346
2-pyrrolidone -286.182660 -286.176157 -286.211594
N-methyl-2-pyrrolidone -325.414344 -325.406237 -325.445537
succindiamide -416.641778 -416.630754 -416.679739
succinic acid -456.382863 -456.373444 -456.417895
dimethyl succinate -534.821912 -534.809146 -534.861731
1,4-diaminobutane -268.662969 -268.653667 -268.694829
1,4-butanediol -308.398662 -308.389599 -308.431007
GVL -345.287656 -345.280001 -345.318290
trans-2-pentenoic acid -345.276556 -345.267597 -345.309435
trans-3-pentenoic acid -345.275064 -345.265945 -345.308534
trans-4-pentenoic acid -345.272437 -345.263501 -345.305838
1-butene -156.906361 -156.900037 -156.933957
E-2-butene -156.910600 -156.904036 -156.937490
isosorbide -534.768448 -534.758255 -534.801938
1,4-sorbitan -611.109429 -611.096872 -611.146845
2,5-anhydrosugar -611.110751 -611.097694 -611.148099

2
ethylene glycole -229.932432 -229.926359 -229.959715
angelilactone I -344.080142 -344.072993 -344.110111
angelilactone II -344.080638 -344.073269 -344.110826
β-acetylacrylic acid -419.232576 -419.222935 -419.267053
valeric acid -346.485688 -346.476175 -346.519641
5-nonanone -428.251223 -428.236686 -428.293408
4-methyl-octane -354.292275 -354.278468 -354.331854
3,4-dimethylseptane -354.290791 -354.277250 -354.329098
levulinic acid -420.446230 -420.435919 -420.482584
formic acid -189.536651 -189.532513 -189.560700
δ-aminolevulinate -475.717276 -475.705907 -475.754841
diglyceraldehyde -612.287418 -612.272523 -612.329343
glyceric acid -418.296100 -418.287325 -418.328718
glycidol -267.934046 -267.927553 -267.962603
propanol -194.024803 -194.018177 -194.052692
pyruvaldehyde -266.783967 -266.777336 -266.812940
1,4-pentanediol -347.639966 -347.629589 -347.674163
diphenolic acid -958.095149 -958.074121 -958.145371
oxalic acid -377.890847 -377.885129 -377.918466
tartronic acid -492.282334 -492.273566 -492.315659
glycolic acid -303.916976 -303.910557 -303.945731
glyoxalic acid -302.713825 -302.707982 -302.741940
hydroxymethyl glyoxal -341.915761 -341.908126 -341.946488
triketo -340.701266 -340.694050 -340.731828
hydroxypyruvic acid -417.094012 -417.085573 -417.126514
dihydroxyacetone -343.117836 -343.109883 -343.148785
glyceric acid -418.296100 -418.287326 -418.328720
ketomalonic acid -491.070433 -491.061709 -491.104790
α-aminoglyceric acid -398.431566 -398.422901 -398.463695
2-keto-glucose -685.058970 -685.044457 -685.099937
glucuronic acid -760.245765 -760.230158 -760.288217
2,5-diketo-gluconic acid -759.042205 -759.027046 -759.084508
gluconic acid -761.445083 -761.429082 -761.487266
5-keto-gluconic acid -760.247496 -760.231840 -760.289806
glucaric acid -835.431220 -835.414947 -835.473928
2-keto-gluconic acid -760.241472 -760.226039 -760.283542
thf-2-one -306.044854 -306.038638 -306.073582
2-methyl-thf -271.298236 -271.290883 -271.328456
3-hydroxypropanoic acid -343.156168 -343.148340 -343.187330
thf -232.056172 -232.050203 -232.084472
glucose (linear) -686.270413 -686.255742 -686.310899

3
Table S2. Water Solvation Energy Contributions in kcal/mol.

Gaussian ADF
Compound
Gsolv(elec) Gsolv(nonelec) Gsolv(total) Gsolv(elec) Gsolv(nonelec) Gsolv(total)
acrylic acid -8.9 4.7 -4.2 -8.6 2.0 -6.6
BH-HMF -15.7 9.4 -6.3 -15.9 2.8 -13.1
C9H18O3 -15.2 10.5 -4.7 -13.8 2.9 -10.9
C9H18O -5.3 9.5 4.2 -4.5 2.7 -1.8
DFF -18.2 6.7 -11.5 -17.0 2.3 -14.7
DHMF -17.7 7.0 -10.7 -17.8 2.4 -15.4
DHM-THF -13.4 7.4 -6.0 -12.3 2.5 -9.9
epichlorhydrin -9.1 4.8 -4.3 -8.0 2.1 -5.9
glucose -21.1 8.4 -12.7 -18.8 2.6 -16.2
glyceraldehyde -12.4 5.1 -7.4 -10.6 2.1 -8.5
glycerin -12.9 5.2 -7.7 -11.4 2.2 -9.3
glycerin carbonate -19.3 5.5 -13.8 -17.4 2.3 -15.1
HMF -13.5 6.9 -6.6 -12.5 2.4 -10.1
lactic acid -14.1 5.3 -8.7 -13.0 2.1 -10.9
methanol -6.5 2.8 -3.7 -5.7 1.8 -4.0
nonane -1.3 10.2 8.9 -1.1 2.8 1.7
propanediol -9.9 4.8 -5.0 -8.8 2.1 -6.7
propylene -2.1 4.1 2.0 -2.0 1.9 -0.1
sorbitol -17.4 8.3 -9.1 -16.5 2.7 -13.8
1,3-propandiol -12.8 5.0 -7.8 -11.5 2.1 -9.3
3-hydroxypropanal -7.9 4.5 -3.4 -7.5 2.0 -5.5
succinonitrile -15.8 6.4 -9.3 -14.7 2.2 -12.5
2-pyrrolidone -12.7 4.5 -8.2 -11.9 2.1 -9.8
N-methyl-2-pyrrolidone -11.3 5.6 -5.8 -10.4 2.3 -8.1
succindiamide -21.8 6.8 -14.9 -21.1 2.4 -18.7
succinic acid -14.9 6.4 -8.5 -13.9 2.3 -11.6

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Dimethyl succinate -11.9 8.4 -3.5 -10.5 2.6 -7.9
1,4-diaminobutane -10.4 6.5 -3.9 -9.4 2.3 -7.1
1,4-butanediol -12.2 6.0 -6.3 -11.1 2.3 -8.8
GVL -12.2 5.5 -6.7 -10.7 2.2 -8.4
trans-2-pentenoic acid -9.5 6.5 -3.0 -9.1 2.3 -6.8
trans-3-pentenoic acid -9.5 6.6 -2.9 -9.2 2.3 -6.9
trans-4-pentenoic acid -9.6 6.7 -2.8 -8.8 2.3 -6.5
1-butene -2.1 5.0 2.9 -2.0 2.1 0.1
E-2-butene -2.0 4.9 2.9 -2.1 2.1 0.0
isosorbide -17.2 6.5 -10.7 -15.4 2.4 -13.0
1,4-sorbitan -16.9 7.6 -9.4 -15.0 2.5 -12.5
2,5-anhydrosugar -19.3 7.9 -11.4 -17.4 2.6 -14.8
ethylene glycol -9.9 3.9 -6.0 -8.9 2.0 -6.9
angelilactone I -13.1 5.4 -7.8 -12.0 -12.0
angelilactone II -9.8 5.3 -4.5 -9.0 2.2 -6.8
β-acetylacrylic acid -13.1 6.9 -6.2 -12.1 2.3 -9.7
valeric acid -8.7 6.8 -1.9 -8.0 2.3 -5.7
5-nonanone -8.1 10.4 2.3 -7.2 2.8 -4.4
4-methyl-octane -1.3 10.1 8.8 -1.1 2.7 1.6
3,4-dimethylseptane -1.3 9.8 8.5 -1.1 2.7 1.6
levulinic acid -14.0 7.1 -6.9 -12.7 2.4 -10.3
formic acid -8.6 3.1 -5.5 -8.0 1.8 -6.2
δ-aminolevulinate -17.1 7.5 -9.6 -15.7 -15.7
diglyceraldehyde -25.2 9.3 -15.9 -22.1 2.7 -19.4
glyceric acid -16.3 5.4 -10.9 -14.6 2.2 -12.5
glycidol -12.2 4.6 -7.6 -10.9 2.1 -8.8
propanol -6.5 4.5 -2.0 -5.9 2.0 -3.9
pyruvaldehyde -7.9 4.9 -3.0 -6.9 2.0 -4.9
1,4-pentanediol -12.4 7.0 -5.3 -11.3 2.4 -8.9

5
diphenolic acid -22.1 15.3 -6.8 -22.5 3.4 -19.0
oxalic acid -14.9 4.6 -10.3 -13.8 2.0 -11.8
tartronic acid -17.3 5.4 -11.9 -15.6 2.2 -13.4
glycolic acid -12.0 4.1 -7.8 -11.2 2.0 -9.2
glyoxalic acid -11.1 4.3 -6.7 -10.0 2.0 -8.0
hydroxymethyl glyoxal -18.6 5.5 -13.1 -13.2 2.1 -11.1
triketo -16.2 5.2 -11.0 -14.1 2.1 -12.1
hydroxypyruvic acid -18.6 5.5 -13.1 -16.8 2.2 -14.6
dihydroxyacetone -13.6 4.9 -8.7 -12.5 2.1 -10.4
glyceric acid -16.3 5.4 -10.9 -14.7 2.2 -12.5
ketomalonic acid -15.5 6.1 -9.5 -14.8 2.2 -12.6
α-aminoglyceric acid -11.9 5.3 -6.6 -11.4 2.2 -9.3
2-keto-glucose -20.2 8.8 -11.4 -18.2 2.6 -15.6
glucuronic acid -23.4 9.4 -14.0 -21.6 2.7 -18.9
2,5-diketo-gluconic acid -25.9 9.4 -16.5 -23.9 2.7 -21.3
gluconic acid -22.3 9.1 -13.2 -20.9 2.7 -18.2
5-keto-gluconic acid -26.6 9.2 -17.4 -24.7 2.7 -22.0
glucaric acid -24.8 9.0 -15.8 -23.2 2.7 -20.5
2-keto-gluconic acid -22.0 9.4 -12.6
thf-2-one -12.0 4.4 -7.7 -10.7 2.1 -8.6
2-methyl-thf -5.0 5.1 0.1 -4.4 2.2 -2.2
3-hydroxypropanoic acid -12.7 5.2 -7.5 -11.9 2.1 -9.8
thf -5.2 4.1 -1.1 -4.4 0.0 -4.4
glucose (linear) -15.7 8.1 -7.6 -14.0 0.0 -14.0

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Table S3. Optimized B3LYP/DZVP2 Cartesian Coordinates in Angstroms for the Various

Structures.

1,4-butanediol (1Ag/C2h)
C -1.88319500 0.50799300 0.00020800
H -1.87017300 1.15587900 -0.88914800
H -1.87030300 1.15520700 0.89005300
C -0.65613200 -0.39855700 -0.00003000
H -0.70747400 -1.05002500 0.88061300
H -0.70780000 -1.04986900 -0.88076400
C 0.65614900 0.39878800 -0.00016900
H 0.70763800 1.05044900 0.88030100
H 0.70780000 1.04987000 -0.88106800
O -3.05377800 -0.32495500 -0.00018700
H -3.83643000 0.24235000 0.00017000
C 1.88305300 -0.50796200 0.00020900
H 1.87002300 -1.15519700 0.89002200
H 1.87004600 -1.15576500 -0.88922100
O 3.05390400 0.32474000 -0.00002900
H 3.83642300 -0.24275400 -0.00053700

1,4-diaminobutane (1A/C2)
C 0.42350400 1.91721100 -0.01745100
H 1.05262900 1.93383800 -0.91509500
H 1.10576100 1.89589600 0.84958300
C -0.42350400 0.63993100 -0.02062100
H -1.08251300 0.64509100 0.85958600
H -1.07870400 0.66170600 -0.89931900
C 0.42350400 -0.63993100 -0.02062100
H 1.08251300 -0.64509100 0.85958600
H 1.07870400 -0.66170600 -0.89931900
C -0.42350400 -1.91721100 -0.01745100
H -1.05262900 -1.93383800 -0.91509500
H -1.10576100 -1.89589600 0.84958300
N -0.43784800 3.11423700 -0.05324600
H -0.98840200 3.17301500 0.80121900
H 0.12887500 3.95803000 -0.09481300
N 0.43784800 -3.11423700 -0.05324600
H 0.98840200 -3.17301500 0.80121900
H -0.12887500 -3.95803000 -0.09481300

1-butene (1A/C1)
C 1.87083100 0.02206700 -0.27670800
H 1.97080400 0.94218800 -0.84774800
H 2.74341900 -0.62326800 -0.22062100

7
C 0.72234400 -0.30355100 0.33308900
H 0.67182700 -1.24037600 0.89059700
C -0.54104700 0.52076700 0.30938300
H -0.36248800 1.44395900 -0.25247400
H -0.79316500 0.81674000 1.33685300
C -1.73700500 -0.24329600 -0.29383500
H -1.93446300 -1.16689700 0.26146600
H -2.64563200 0.36702500 -0.26397900
H -1.54103400 -0.51529200 -1.33566600

E-2-butene (1Ag/C2h)
C 0.54902200 1.89305200 0.00001100
H 1.07058300 2.28817700 0.88071300
H -0.47026300 2.29037500 -0.00001800
H 1.07059400 2.28815400 -0.88070700
C 0.54902200 0.38462400 -0.00000400
H 1.52643300 -0.09974100 -0.00002700
C -0.54902200 -0.38462400 -0.00000400
H -1.52643300 0.09974100 -0.00002700
C -0.54902200 -1.89305200 0.00001100
H 0.47026300 -2.29037500 -0.00001800
H -1.07058300 -2.28817700 0.88071300
H -1.07059400 -2.28815400 -0.88070700

2-pyrrolidone (1A/C1)
C -0.00641600 1.22708600 0.12862700
C -1.42082800 0.69597700 -0.17770800
C -1.33024100 -0.81926900 0.13357700
H 0.33018500 2.02386900 -0.53657700
H 0.08846600 1.59237600 1.15737200
H -1.65049100 0.83517300 -1.23786500
H -2.20447100 1.18508600 0.40452600
H -1.62516200 -1.03381000 1.16995900
H -1.96114400 -1.41726000 -0.53067000
N 0.08567000 -1.10006000 -0.08640400
H 0.48760000 -2.02555200 -0.01888100
C 0.90430000 0.00185200 -0.00843900
O 2.13180500 -0.01166700 -0.03242200

DFF (1A1/C2v)
C 0.33278900 0.00001200 1.09335900
C 1.66202800 -0.00004800 0.71095000
C 1.66202800 -0.00004800 -0.71095000
C 0.33278900 0.00001200 -1.09335900
O -0.47864700 0.00007200 0.00000000
H 2.51534800 -0.00000400 1.37448500

8
H 2.51534800 -0.00000400 -1.37448500
C -0.25149500 0.00004000 -2.44208200
H 0.51496800 0.00010900 -3.24353100
C -0.25149500 0.00004000 2.44208200
H 0.51496800 0.00010900 3.24353100
O -1.44695700 -0.00005200 -2.69308000
O -1.44695700 -0.00005200 2.69308000

DHMF (1A′/Cs)
C 1.10585500 0.37202800 0.18332200
C 0.71847400 1.58975100 -0.30840400
C -0.71836300 1.58982100 -0.30840300
C -1.10589200 0.37212000 0.18324100
O -0.00003100 -0.37741800 0.49504300
H 1.37742500 2.38030500 -0.63751800
H -1.37724000 2.38042100 -0.63756600
C 2.44293900 -0.23351500 0.44029400
H 2.43131800 -0.73273200 1.41883600
H 3.18207300 0.57801600 0.47382100
C -2.44298500 -0.23338900 0.44020700
H -2.43140500 -0.73250700 1.41878800
H -3.18214900 0.57813000 0.47365500
O 2.76307100 -1.17377000 -0.60172200
H 3.52432100 -1.69606800 -0.31243800
O -2.76316100 -1.17374900 -0.60173300
H -3.52353300 -1.69697200 -0.31181900

DHM-THF (1A/C1)
C 1.15885800 0.05447200 0.46810900
O 0.03002200 -0.79947500 0.73333200
C -1.19769900 -0.04648800 0.62110700
C -0.79960700 1.38776700 0.21601900
C 0.60839500 1.20515300 -0.37955700
H 1.55544900 0.44391400 1.41809300
H -1.71200900 -0.06182100 1.58937500
H -1.52029000 1.82252700 -0.47964900
H -0.75720000 2.03104800 1.10017000
H 0.55699900 0.90148800 -1.43097900
H 1.22640300 2.10246900 -0.31529500
C -2.08620100 -0.75796400 -0.40008500
H -2.15879700 -1.81763900 -0.12212100
H -1.63098900 -0.69201900 -1.39905900
C 2.23859300 -0.79597600 -0.19036700
H 2.45825500 -1.65849900 0.45288100
H 1.87059800 -1.16786800 -1.15717100
O -3.37260300 -0.12158600 -0.37499000

9
H -3.96751800 -0.60293100 -0.96452400
O 3.39612500 0.03633900 -0.35797400
H 4.11671700 -0.50466900 -0.70602800

Dimethyl succinate (1Ag/C2h)

C -1.92975500 0.18803300 -0.00064600
C -0.57803800 -0.49976200 -0.00100600
H -0.52809300 -1.16331600 0.86741300
H -0.52729000 -1.15987100 -0.87205300
C 0.57803600 0.49976000 0.00130500
H 0.52790600 1.16346900 -0.86698700
H 0.52747500 1.15971400 0.87247900
C 1.92975300 -0.18803300 0.00048100
O -2.11720000 1.39367600 -0.00105200
O 2.11720400 -1.39367300 -0.00010000
O -2.93379500 -0.72456700 0.00021200
O 2.93379600 0.72457200 0.00048000
C -4.27135200 -0.17731900 0.00069700
H -4.93826400 -1.03974900 0.00263800
H -4.43197900 0.43688700 0.89003500
H -4.43375900 0.43417500 -0.89022400
C 4.27135000 0.17731600 -0.00044100
H 4.43202100 -0.43606400 -0.89034100
H 4.93826700 1.03974400 -0.00154600
H 4.43370900 -0.43500800 0.88991900

Epichlorohydrin (1A/C1)
C -2.16454700 0.31508900 -0.01373700
C -0.78891700 0.08535900 0.48403100
O -1.46853200 -0.91706100 -0.28903800
H -3.00034600 0.23305100 0.67935600
H -2.32325700 0.95705100 -0.87940700
H -0.65558100 -0.17596000 1.53357300
C 0.37997200 0.77434600 -0.16768800
H 0.57546600 1.73969100 0.30398800
H 0.20724500 0.90634200 -1.23593400
Cl 1.90504000 -0.19838000 0.00559400

Glucose (1A/C1)
C -1.11741600 1.00624200 0.20965800
C 0.32403900 1.26644600 -0.23598700
C 1.22902600 0.11607800 0.24561400
C -0.57077200 -1.43280300 0.27056700
C -1.57069600 -0.38258500 -0.22801400
H 0.35038000 1.31722400 -1.33269000
H -1.15235700 1.06328200 1.30792500

10
H -0.53756700 -1.41991400 1.37449700
H -1.58971700 -0.42955200 -1.32565000
H 1.24872300 0.10852400 1.34584900
O 0.71602000 -1.13189200 -0.24432100
C 2.66189000 0.20346100 -0.27523400
H 3.13749200 1.11578500 0.09618700
H 2.64228700 0.23752300 -1.37579900
O 3.45672900 -0.88222900 0.18661600
H 2.96679200 -1.69442400 -0.01747700
O -0.88100100 -2.72029400 -0.19669300
H -1.84314900 -2.82247100 -0.12301900
O -2.84765900 -0.72947400 0.31015400
H -3.46948100 -0.02680300 0.06730100
O -2.03377000 1.94948200 -0.35215300
H -1.74867800 2.83172700 -0.06978100
O 0.69627300 2.53099700 0.33644500
H 1.40611600 2.92533900 -0.18735300

Glyceraldehyde (1A/C1)
C -1.37959900 -0.15936500 0.53578500
H -2.08258500 0.63476500 0.82119200
H -1.50319400 -0.99385100 1.23368500
C 0.04809500 0.40307800 0.63517200
H 0.20586300 0.74687800 1.67384000
C 1.09410600 -0.67004900 0.37790600
H 1.01789400 -1.59369800 0.98434600
O -1.66118400 -0.65936800 -0.76505800
H -1.48669800 0.06261000 -1.38873100
O 0.20509000 1.47428900 -0.27680700
H 1.03851900 1.30303600 -0.75414900
O 1.98541700 -0.51513700 -0.44105600

Glycerin (1A/C1)
C 1.28474900 -0.70639700 0.20506400
H 1.32820400 -1.71707300 -0.21191100
H 1.27799500 -0.78045000 1.30300100
C 0.01319300 0.00109800 -0.25832700
H 0.01598700 0.05805100 -1.35640800
C -1.25587900 -0.71478800 0.19283600
H -1.26686700 -0.79256600 1.28821900
H -1.29278600 -1.72355000 -0.24203100
O 2.45468200 -0.02818500 -0.24724500
H 2.34015200 0.90621600 -0.01392600
O 0.06722500 1.32650500 0.28992200
H -0.77221200 1.75909800 0.07049800
O -2.36059400 0.08119900 -0.27102700

11
H -3.17335200 -0.22535300 0.15191600

Glycerin carbonate (1A/C1)

C 0.27324600 1.49668600 -0.01416200
C -0.62018200 0.29910600 -0.38833800
H 0.23534200 2.30504700 -0.74614300
H 0.04602500 1.89105700 0.98291200
H -0.86801700 0.28571800 -1.45458600
O 1.60003100 0.94510900 -0.00064700
O 0.23741800 -0.83397900 -0.12584700
C 1.52851700 -0.42138100 0.02015700
O 2.47497000 -1.15085400 0.15085000
C -1.90147400 0.21667400 0.42354100
H -2.36422000 1.21696800 0.43742100
H -1.64970900 -0.06427300 1.45517100
O -2.76453400 -0.73538100 -0.19310100
H -3.46313500 -0.98019000 0.42799600

GVL (1A/C1)
C -1.05598100 -0.04206100 0.40417100
O 0.05327300 -0.95905100 0.16509900
C 0.94875500 1.22430700 0.03718600
C -0.57198400 1.31449400 -0.14260600
H -1.18703200 0.01244800 1.49266200
H 1.27505600 1.59049600 1.01705200
H 1.53882800 1.73671800 -0.72322000
H -1.02966300 2.15314500 0.38693300
H -0.82834700 1.39765500 -1.20355700
C 1.22527900 -0.27717200 -0.01027600
C -2.31307800 -0.60296700 -0.24175500
H -2.56043500 -1.58284000 0.17508000
H -3.15565100 0.07287000 -0.06046900
H -2.17554800 -0.70886700 -1.32188200
O 2.28733300 -0.83735300 -0.17046500

Lactic acid (1A/C1)

C 1.35227800 1.05839200 0.61141200
H 0.89018500 2.04908300 0.59307100
H 1.26997300 0.63809600 1.61739200
H 2.41340200 1.17328800 0.36429700
C 0.67682900 0.12933900 -0.41245000
H 0.75506500 0.57373800 -1.41280400
C -0.82110900 0.06957500 -0.11932900
O -1.60732400 0.91152900 -0.51929700
O -1.18460000 -0.96844000 0.66917700
H -2.14568100 -0.88131300 0.80411500

12
O 1.21579800 -1.19000700 -0.39697100
H 2.17806400 -1.12138700 -0.46714000

Methanol (1A′/Cs)
C 0.04682900 0.67016800 0.00000000
H 1.09363900 0.98234200 0.00000000
H -0.44003700 1.08177900 0.89485800
H -0.44003700 1.08177900 -0.89485800
O 0.04682900 -0.76209900 0.00000000
H -0.86916500 -1.07011600 0.00000000

N-methyl-2-pyrrolidone (1A/C1)
C -1.33581100 0.92045100 0.12452300
C -1.79987200 -0.51705500 -0.17748000
C -0.55379100 -1.38222300 0.12472500
H -1.74604900 1.67688100 -0.54659600
H -1.56925000 1.22800900 1.15014800
H -2.06291500 -0.61210300 -1.23469000
H -2.66475100 -0.82644200 0.41323000
H -0.56838600 -1.77598900 1.15232200
H -0.46201000 -2.23543300 -0.55644400
N 0.55602300 -0.45385400 -0.05726800
C 0.18799000 0.86829700 -0.00494300
C 1.93970900 -0.88252500 -0.01229500
H 2.56859300 0.00239800 -0.12185500
H 2.17410600 -1.37132900 0.94274500
H 2.15626600 -1.58484700 -0.82559900
O 0.95661100 1.82927200 -0.03744600

1,2-Propanediol (1A/C1)
C 0.72286500 -0.73220900 0.21394600
C -0.46753700 0.05074500 -0.33807400
H 0.64149800 -0.79430100 1.30763400
H 0.73300600 -1.74747900 -0.20671200
C -1.80001900 -0.59346000 0.02982300
H -0.36550400 0.08638300 -1.43405100
H -2.62234900 0.00536000 -0.37006700
H -1.87395600 -1.60437800 -0.38425300
H -1.91493200 -0.64562800 1.11712700
O -0.46376500 1.38460300 0.18349200
H 0.44012000 1.71936900 0.07329500
O 1.90971500 -0.01184400 -0.16729900
H 2.66266200 -0.35185400 0.33330800

Propylene (1A′/Cs)
C -0.13312800 -0.45739800 -0.00020600

13
H -0.16845000 -1.54736200 0.00036200
C -1.28802100 0.22279400 -0.00006800
H -2.24516400 -0.29167400 0.00050700
H -1.30853500 1.30999000 0.00011100
C 1.24021100 0.16417700 0.00003000
H 1.81224300 -0.15192500 0.88104900
H 1.81300000 -0.15263900 -0.88021100
H 1.18253000 1.25617000 -0.00035300

Succindiamide (1Ag/Ci)
C -0.40838100 1.88563200 -0.26976200
C -0.23427100 0.55793000 0.46569800
H 0.47144000 0.68417100 1.29223800
H -1.18911600 0.28475800 0.92841000
C 0.23427100 -0.55793000 -0.46569800
H -0.47144000 -0.68417100 -1.29223800
H 1.18911600 -0.28475800 -0.92841000
C 0.40838100 -1.88563200 0.26976200
O -0.29993300 2.00596000 -1.49085900
O 0.29993300 -2.00596000 1.49085900
N 0.68768200 -2.96004200 -0.54226300
H 0.92133500 -3.83760700 -0.09914900
H 0.89519900 -2.83799800 -1.52213500
N -0.68768200 2.96004200 0.54226300
H -0.89519900 2.83799800 1.52213500
H -0.92133500 3.83760700 0.09914900

Succinic acid (1Ag/C2h)

C -0.04443400 1.93322100 -0.09006300
C -0.04779700 0.55087100 0.52727500
H 0.78003000 0.49133800 1.24021300
H -0.95614700 0.44692300 1.12854000
C 0.04779700 -0.55087100 -0.52727500
H -0.78003000 -0.49133800 -1.24021300
H 0.95614700 -0.44692300 -1.12854000
C 0.04443400 -1.93322100 0.09006300
O 0.01892100 2.19021600 -1.27969600
O -0.01892100 -2.19021600 1.27969600
O -0.12361100 2.90449900 0.86356300
H -0.11800200 3.75664600 0.39159100
O 0.12361100 -2.90449900 -0.86356300
H 0.11800200 -3.75664600 -0.39159100

Succinonitrile (1Ag/C2h)
C 0.42633600 1.84662800 0.00000000
C -0.42633600 0.64805500 0.00000000

14
H -1.07173000 0.67708900 0.88249200
H -1.07173000 0.67708900 -0.88249200
C 0.42633600 -0.64805500 0.00000000
H 1.07173000 -0.67708900 0.88249200
H 1.07173000 -0.67708900 -0.88249200
C -0.42633600 -1.84662800 0.00000000
N 1.11076000 2.78924000 0.00000000
N -1.11076000 -2.78924000 0.00000000

2,5-diketo-gluconic acid (1A/C1)

C 0.82309385 0.56290404 -0.42427109
C -0.44053014 -0.31166896 -0.26137700
H 0.84924085 0.89917294 -1.47498612
O 0.89485585 1.67621912 0.45303781
H 0.17413784 2.28011109 0.21254075
O -0.49669513 -1.05237584 0.94674307
H 0.12198288 -1.79410385 0.85604114
H -0.48600713 -0.98438704 -1.13285094
C -3.01993214 -0.17142294 0.11466199
O -3.77763814 0.27858613 0.94324695
O -3.21149113 -1.31750901 -0.58265490
H -4.05389413 -1.70513699 -0.28014686
C 3.33677086 0.44272412 0.17732392
H 3.14027886 0.86563421 1.17347888
H 3.45763185 1.29954405 -0.50460916
O 4.44530686 -0.43672488 0.15461600
H 5.19956986 0.01764117 0.55298496
C 2.07957786 -0.30071693 -0.23392601
O 2.04082787 -1.50567595 -0.43059089
C -1.71283715 0.52623002 -0.32454708
O -1.74514116 1.68663399 -0.69560319

2-keto-gluconic acid (1A/C1)

C 2.03356693 -0.17343891 0.18960307
H 2.00625087 -0.23746896 1.28480107
C 0.80433895 0.62670611 -0.25772095
C -0.45983105 -0.26947590 -0.21484707
O 1.94098497 -1.49209188 -0.37789100
H 2.81730097 -1.89556588 -0.26741097
H 0.93038601 0.94188216 -1.30452493
O 0.74560990 1.76196506 0.59915910
H 0.03163691 2.33342907 0.27573209
O -0.58401210 -1.08198196 0.94442689
H 0.06160791 -1.80003795 0.84537788
H -0.43492299 -0.89893686 -1.11911410
C -3.05176006 -0.19219993 0.05306780

15
O -3.82361011 0.20691002 0.89528677
O -3.23078001 -1.30059890 -0.70737227
H -4.07438403 -1.70565491 -0.43244133
C 3.33962595 0.49259412 -0.22638482
H 3.42095592 1.47093109 0.25965223
H 3.36154801 0.61980917 -1.31765182
O 4.38835593 -0.39813090 0.19737019
H 5.23961195 -0.05504888 -0.10447075
C -1.74561204 0.53660009 -0.33523310
O -1.79679403 1.69167211 -0.72233704

2-keto-glucose (1A/C1)
C 0.49471708 0.58067205 -0.20237807
C -0.68588994 -0.42205394 -0.29306094
H 0.59876005 1.03142396 -1.20097611
O 0.32402811 1.59285214 0.78278685
H -0.44405289 2.12450613 0.51925882
O -0.72548992 -1.40280585 0.73825215
H 0.03194907 -1.99167887 0.58228818
H -0.60294697 -0.91324203 -1.27822990
O -4.36153992 -0.19304686 0.22248613
C 3.03261508 0.66600703 -0.17174714
H 3.02971310 1.59525808 0.40848877
H 3.03927405 0.90143993 -1.24507516
O 4.15607308 -0.16737096 0.16752990
H 4.97362208 0.27665501 -0.09314416
C -2.04441693 0.26772407 -0.30025197
O -2.19533092 1.45800305 -0.52450907
C -3.27655493 -0.65040290 -0.07005085
H -3.10412595 -1.73432891 -0.20350276
C 1.79133908 -0.14900393 0.17020697
H 1.77361210 -0.32229883 1.25366798
O 1.81571004 -1.41057899 -0.52277992
H 2.72573504 -1.74180900 -0.44921192

2-methyl-thf (1A/C1)
C 0.73352400 -0.01096800 0.38082200
O 0.01152000 -1.12011600 -0.17734900
C -1.37361000 -0.85094600 0.05651700
C -1.55235200 0.67816500 -0.12409700
C -0.10557200 1.22910200 0.00216200
H 0.74410500 -0.11877500 1.47920800
H -1.95254800 -1.44902800 -0.65131800
H -1.64668600 -1.15626400 1.07859600
H -1.97460900 0.91149300 -1.10431400
H -2.22349300 1.09062200 0.63427400

16
H 0.24061400 1.63094300 -0.95453900
H -0.01835500 2.02117800 0.75119500
C 2.16134800 -0.02588100 -0.14549500
H 2.72852500 0.81422100 0.26900100
H 2.66645700 -0.95496400 0.13424400
H 2.16380900 0.05467200 -1.23701400

3-hydroxypropanoic acid (1A′/Cs)

C 0.99732700 -0.50232200 0.00000000
O 0.73086000 -1.69214500 0.00000000
O 2.28224900 -0.04445000 0.00000000
H 2.85570900 -0.83210800 0.00000000
C 0.00000000 0.63366600 0.00000000
H 0.18930600 1.26352300 0.87570600
H 0.18930600 1.26352300 -0.87570600
C -1.44407400 0.14144700 0.00000000
H -1.62790100 -0.47775400 0.88696400
H -1.62790100 -0.47775400 -0.88696400
O -2.27533600 1.31081600 0.00000000
H -3.20022300 1.03005800 0.00000000

5-keto-gluconic acid (1A/C1)

C -0.76921692 0.79059915 0.26126209
C 0.36850201 -0.24463493 0.14814306
H -0.55656289 1.41859309 1.13209313
O -0.91473084 1.58793922 -0.91394887
H -0.24170779 2.28363517 -0.87417783
O -0.02763305 -1.24900785 -0.78222899
H 0.59523390 -1.98767290 -0.72723902
H 0.50654596 -0.67070298 1.15025905
C 2.91167900 -0.36924010 0.01132810
O 3.86222603 0.08588680 0.62322914
O 2.84915292 -1.65522308 -0.41868396
H 3.67405088 -2.09521315 -0.14185397
C -3.13988796 0.04472736 -0.50576598
H -2.66929997 -0.37340263 -1.40842799
H -3.37944688 1.09467639 -0.72950294
O -4.27028102 -0.69697258 -0.07802004
H -4.92103601 -0.68238350 -0.79226005
C 1.67552207 0.44596000 -0.33989988
H 1.60624109 0.49531506 -1.43511188
O 1.81114515 1.74906897 0.20335918
H 2.69242315 1.80091588 0.61474120
C -2.07703998 0.04144623 0.57656404
O -2.20035304 -0.51380481 1.65400501

17
Glucaric acid (1A/C1)
C 1.83338996 -0.66837598 0.05523843
H 1.84356303 -1.16850617 1.03216885
C 0.67205699 0.37040507 0.07734167
C -0.67205699 -0.37040507 0.07734167
C -1.83338996 0.66837598 0.05523843
O 1.63077286 -1.61076683 -0.98269177
H 2.42426981 -1.58741631 -1.54552685
H -1.84356303 1.16850617 1.03216885
H 0.71146593 0.97049831 -0.84004483
O 0.70978410 1.19288003 1.23749398
H 1.55516511 1.66257803 1.26306653
O -1.63077286 1.61076683 -0.98269177
H -2.42426981 1.58741631 -1.54552685
O -0.70978410 -1.19288003 1.23749398
H -1.55516511 -1.66257803 1.26306653
H -0.71146593 -0.97049831 -0.84004483
C -3.18947404 0.00408696 -0.15361372
C 3.18947404 -0.00408696 -0.15361372
O 3.94192088 -0.28923295 -1.06967705
O -3.94192088 0.28923295 -1.06967705
O -3.49411999 -0.94230926 0.77494208
H -4.37244501 -1.29663544 0.54326845
O 3.49411999 0.94230926 0.77494208
H 4.37244501 1.29663544 0.54326845

Gluconic acid (1A/C1)

C 2.05739409 -0.32238885 0.00372211
H 2.07243614 -0.93613684 0.91202613
C 0.78510903 0.52976706 -0.00876290
C -0.47505091 -0.35662703 0.06176312
C -1.74139597 0.52837388 0.27231211
O 1.99601115 -1.16208288 -1.15725287
H 2.87700717 -1.55790082 -1.24719786
H -1.81599098 0.70020890 1.35465911
H 0.74502099 1.06258503 -0.96567291
O 0.86118997 1.46399408 1.07363308
H 0.24932691 2.18652503 0.86868607
O -1.64448006 1.76816288 -0.41333591
H -2.44452807 1.85718581 -0.96114391
O -0.35490584 -1.27234500 1.14711014
H -1.04879279 -1.94100405 1.06281816
H -0.53616187 -0.89317406 -0.89343387
C -3.01039592 -0.18111122 -0.17318087
O -3.80175996 0.29514071 -0.96974088
O -3.17845683 -1.40234322 0.39619415

18
H -4.00790681 -1.77302828 0.04273716
C 3.31898003 0.53707424 -0.03222491
H 3.39437599 1.12535326 0.88733908
H 3.28666798 1.21249822 -0.89860492
O 4.42023609 -0.38646269 -0.15550089
H 5.23802706 0.11384837 -0.27283890

Glucuronic acid (1A/C1)

C -2.12989302 -0.44928593 0.13647601
H -2.15966605 -1.08630981 -0.75108208
C -0.88798200 0.43997304 0.11697511
C 0.40706098 -0.39340099 0.03627597
C 1.61083200 0.53787703 -0.29350193
O -2.07264902 -1.22337410 1.34850490
H -2.71436104 -1.94415708 1.27461881
H 1.59936898 0.68246818 -1.38256591
H -0.85159996 0.99801390 1.06028418
O -1.05248599 1.33556720 -0.98436376
H -0.49807197 2.11167716 -0.81416367
O 1.49583305 1.78724694 0.36990825
H 2.33423406 1.94357185 0.83984026
O 0.26550993 -1.38401984 -0.97707317
H 1.04865492 -1.95281986 -0.96492826
H 0.54777699 -0.86084213 1.01996690
C -3.40448400 0.39595009 0.19191715
H -3.36869596 1.26876000 0.87781127
O -4.42876001 0.09997120 -0.39711987
C 2.94403999 -0.09556806 0.07518096
O 3.76822102 0.44386682 0.79263902
O 3.12748095 -1.32503299 -0.47251821
H 3.99971694 -1.64743505 -0.17953828

THF-2-one (1A/C1)
O 0.12739528 -1.13994176 -0.04664026
C -1.27654483 -0.82413917 0.12430661
C -1.41375021 0.67401183 -0.20728925
C -0.02330240 1.21238917 0.15863197
H -1.84231757 -1.47774826 -0.54202553
H -1.55140989 -1.04455336 1.16190255
H -1.60504112 0.80679989 -1.27566526
H -2.22807440 1.14358654 0.34831171
H 0.33621745 2.02955434 -0.46725890
H 0.03589839 1.53818508 1.20298701
C 0.88926496 -0.00314056 0.00306895
O 2.09769497 -0.02887722 -0.06592991

19
THF (1A/C2)
O 0.00013500 -1.25829900 -0.00088200
C -1.17132500 -0.43052800 0.13096100
C -0.73700300 1.00011800 -0.22418200
C 0.73638500 1.00072500 0.22366100
C 1.17176300 -0.43010600 -0.12989000
H -1.94883300 -0.82194300 -0.53345700
H -1.53688300 -0.48776000 1.16621400
H -1.34332400 1.75864800 0.27773100
H -0.80574000 1.16212100 -1.30495600
H 1.34233900 1.75918500 -0.27874300
H 0.80476900 1.16355500 1.30433200
H 1.94777400 -0.82061500 0.53680000
H 1.53989100 -0.48805700 -1.16417000

Nonane (1A1/C2v)
C 0.000000 5.132356 0.372649
C 0.000000 3.854560 -0.479748
H 0.000000 6.031264 -0.252942
H -0.884045 5.175517 1.019112
H 0.884045 5.175517 1.019112
C 0.000000 2.568930 0.360763
H -0.877737 3.855497 -1.139227
H 0.877737 3.855497 -1.139227
C 0.000000 1.284769 -0.481477
H 0.878005 2.570210 1.021496
H -0.878005 2.570210 1.021496
H -0.878003 1.284931 -1.142117
H 0.878003 1.284931 -1.142117
C 0.000000 0.000000 0.360154
C 0.000000 -1.284769 -0.481477
H -0.877943 0.000000 1.020821
H 0.877943 0.000000 1.020821
C 0.000000 -2.568930 0.360763
H -0.878003 -1.284931 -1.142117
H 0.878003 -1.284931 -1.142117
C 0.000000 -3.854560 -0.479748
H 0.878005 -2.570210 1.021496
H -0.878005 -2.570210 1.021496
H -0.877737 -3.855497 -1.139227
H 0.877737 -3.855497 -1.139227
C 0.000000 -5.132356 0.372649
H 0.000000 -6.031264 -0.252942
H 0.884045 -5.175517 1.019112
H -0.884045 -5.175517 1.019112

20
Sorbitol (1A1/C2v)

C -3.129020 -0.692352 0.256545

C -1.946316 0.129210 -0.249552
H -3.063108 -1.714010 -0.126816
H -3.124346 -0.708967 1.354621
C -0.603818 -0.393552 0.286106
H -1.930958 0.074781 -1.347439
C 0.603818 0.393552 -0.286106
H -0.596127 -0.273960 1.381736
H 0.596127 0.273960 -1.381736
C 1.946316 -0.129210 0.249552
C 3.129020 0.692352 -0.256545
H 1.930958 -0.074781 1.347439
H 3.124346 0.708967 -1.354621
H 3.063108 1.714010 0.126816
O 2.108025 -1.499072 -0.162678
H 3.031543 -1.735959 0.020508
O 0.569875 1.773481 0.078720
H -0.361774 2.061403 0.076882
O -0.569875 -1.773481 -0.078720
H 0.361774 -2.061403 -0.076882
O -2.108025 1.499072 0.162678
H -3.031543 1.735959 -0.020508
O -4.306745 -0.017560 -0.233997
H -5.090590 -0.432816 0.148317
O 4.306745 0.017560 0.233997
H 5.090590 0.432816 -0.148317

Acrylic acid (1A′/Cs)

C -0.300263 -1.912839 0.000000
C -0.816584 -0.674716 0.000000
H -0.947398 -2.785515 0.000000
H 0.772309 -2.076358 0.000000
H -1.886529 -0.493475 0.000000
C 0.000000 0.565297 0.000000
O -0.472443 1.692351 0.000000
O 1.347136 0.341238 0.000000
H 1.765160 1.220185 0.000000

BH-HMF (1A/C1)
C 0.273358 0.240639 -0.126681
C 0.870003 1.476294 -0.212729
C 2.287181 1.269248 -0.114471
C 2.465239 -0.078942 0.025472
O 1.258163 -0.722406 0.020920

21
 H 0.360487 2.421478 -0.333376
H 3.073353 2.008069 -0.142080
C 3.674398 -0.948220 0.177924
H 3.600718 -1.516194 1.118209
H 3.709474 -1.675652 -0.647696
C -1.090251 -0.255611 -0.158833
H -1.203545 -1.331239 -0.068771
C -2.192343 0.504897 -0.289850
H -2.109678 1.585902 -0.385063
C -3.600996 -0.029184 -0.319895
H -4.040876 0.240965 -1.295728
C -4.466479 0.600758 0.785858
H -4.479587 1.691767 0.692616
H -5.502437 0.247638 0.715825
H -4.069216 0.337516 1.770068
O 4.825598 -0.100491 0.172377
H 5.611408 -0.656927 0.250338
O -3.559082 -1.457916 -0.202914
H -4.468191 -1.786103 -0.198165

HMF (1A/C1)
C 1.128364 0.002435 0.038356
C 0.923333 1.344684 -0.188783
C -0.481105 1.564880 -0.069341
C -1.047529 0.346183 0.226445
O -0.079348 -0.614648 0.298759
H 1.699127 2.062056 -0.413265
H -1.013179 2.497419 -0.191215
C -2.458686 -0.101791 0.453778
H -2.513465 -0.685509 1.382851
H -3.090502 0.781115 0.568304
H 2.126871 -1.907110 0.276051
C 2.321762 -0.837949 0.056736
O -3.006477 -0.841601 -0.645479
H -2.494256 -1.655890 -0.752703
O 3.456897 -0.419093 -0.149925

C9H18O3 (1A/C1)
C 2.555602 -0.122897 -0.421873
O 1.330910 -0.853279 -0.210825
C 0.290334 0.029507 0.270312
C 0.768807 1.441249 -0.098172
C 2.293316 1.316742 0.053860
H 2.785849 -0.134518 -1.496138
H 0.239947 -0.061474 1.367802
H 0.500277 1.666183 -1.137197

22
 H 0.337613 2.214113 0.543549
H 2.854788 2.050960 -0.526659
H 2.585718 1.425008 1.104209
C -1.044467 -0.414641 -0.323044
H -1.193328 -1.473401 -0.093869
H -0.988456 -0.326437 -1.415480
C -2.235988 0.391762 0.214915
H -2.136830 1.447310 -0.065647
H -2.251939 0.350376 1.311859
C -3.587708 -0.112335 -0.295254
H -3.558744 -0.141120 -1.396406
C -4.749086 0.782527 0.149707
H -4.631425 1.798958 -0.241387
H -5.706770 0.394516 -0.216932
H -4.797086 0.830728 1.242269
C 3.680348 -0.844391 0.316039
H 3.723554 -1.886365 -0.027365
H 3.466189 -0.842209 1.394675
O -3.748342 -1.455102 0.204983
H -4.585116 -1.807801 -0.127523
O 4.903824 -0.149933 0.026602
H 5.637671 -0.643441 0.415225

C9H18O (1A/C1)
C -2.692722 -0.106615 0.354788
O -1.512484 -0.894107 0.144125
C -0.395778 -0.040121 0.434294
C -0.796904 1.349830 -0.124928
C -2.343695 1.282855 -0.225308
H -2.859929 -0.011937 1.441640
H -0.288067 0.030683 1.530676
H -0.453481 2.157483 0.527209
H -0.348845 1.506559 -1.110671
H -2.840594 2.086693 0.325390
H -2.667984 1.342487 -1.268433
C 0.870418 -0.656588 -0.152077
H 0.942554 -1.692288 0.201233
H 0.764145 -0.701144 -1.243265
C 2.148459 0.107818 0.225678
H 2.083147 1.143685 -0.132505
H 2.229061 0.166059 1.320044
C 3.423567 -0.536617 -0.337850
H 3.496758 -1.569821 0.025315
H 3.343207 -0.601384 -1.430616
C 4.701064 0.229218 0.036588
H 5.592121 -0.253855 -0.377877

23
 H 4.671444 1.256959 -0.343141
H 4.825633 0.282169 1.124253
C -3.886089 -0.805010 -0.281048
H -4.037093 -1.793665 0.162299
H -4.796666 -0.215892 -0.128706
H -3.725465 -0.928559 -1.356659

trans-2-pentenoic acid (1A′/Cs)

C -3.113621 0.278120 0.539096
C -2.147284 -0.381456 -0.467220
H -2.819933 0.053169 1.568710
H -3.122764 1.366779 0.421043
H -4.134004 -0.086567 0.386701
H -2.496439 -0.163309 -1.485751
H -2.161140 -1.469574 -0.349497
C -0.741960 0.132483 -0.328883
C 0.336030 -0.631199 -0.077705
H -0.599497 1.206714 -0.435329
H 0.263232 -1.707419 0.043858
C 1.711729 -0.106655 0.056617
O 2.693183 -0.801067 0.283285
O 1.812354 1.250473 -0.095294
H 2.756882 1.457203 0.014912

trans-3-pentenoic acid (1A′/Cs)

C 3.332005 0.268817 -0.213618
H 4.109416 -0.315600 0.293676
H 3.666327 0.411970 -1.248383
H 3.271641 1.249629 0.266028
C 2.005573 -0.445302 -0.171481
C 0.890792 0.045592 0.385469
H 1.972072 -1.431144 -0.637430
H 0.897811 1.033707 0.840238
C -0.419528 -0.698301 0.432449
H -0.648841 -1.016162 1.460679
H -0.392562 -1.609713 -0.170313
C -1.607168 0.145548 0.000994
O -1.655367 1.361294 -0.033467
O -2.679783 -0.635738 -0.323713
H -3.404711 -0.025259 -0.549939

trans-4-pentenoic acid (1A′/Cs)

C 3.300559 -0.051905 -0.425752
C 2.248187 -0.178841 0.393969
H 4.246343 -0.541350 -0.210063
H 3.247684 0.548318 -1.330900

24
 H 2.352492 -0.791540 1.290735
C 0.903820 0.471218 0.181654
C -0.227868 -0.565329 0.093327
H 0.920300 1.080167 -0.726681
H 0.685714 1.153510 1.011747
H -0.089166 -1.234874 -0.762181
H -0.242378 -1.212944 0.978507
C -1.601347 0.063955 -0.023672
O -1.857599 1.253939 0.019658
O -2.572805 -0.883163 -0.185116
H -3.417859 -0.402090 -0.244650

Dihydroxyacetone (1A/C2)
C 0.422956 -1.197781 -0.306687
H 0.561929 -1.185690 -1.397513
H 0.159355 -2.213404 0.005496
C -0.767924 -0.287948 0.008245
C -0.495418 1.185853 0.323689
H -1.393606 1.749511 0.063539
H -0.352069 1.263772 1.413401
O 0.595579 1.744751 -0.397525
H 1.388438 1.246043 -0.140580
O 1.597215 -0.719482 0.372266
H 2.340664 -1.300122 0.161155
O -1.900594 -0.745377 -0.006863

Glucose (linear) (1A/C1)

C -3.028553 -0.719090 0.132903
C -1.827999 0.132564 -0.271508
H -2.937175 -1.719364 -0.298982
H -3.077868 -0.793143 1.227455
C -0.510341 -0.406209 0.306239
H -1.758404 0.134567 -1.368602
C 0.715138 0.410563 -0.177072
H -0.559088 -0.337636 1.405212
H 0.786314 0.285478 -1.269099
C 2.030748 -0.094086 0.471302
H 1.961966 0.126936 1.547639
O 2.245975 -1.483313 0.273137
H 3.102539 -1.558461 -0.193254
O 0.650869 1.788465 0.180798
H -0.286358 2.062127 0.167472
O -0.434036 -1.762984 -0.124774
H 0.490092 -2.055263 -0.019358
O -2.015334 1.478670 0.203008

25
 H -2.928872 1.725568 -0.014872
O -4.182132 -0.022516 -0.380513
H -4.983296 -0.461536 -0.066558
C 3.218151 0.684033 -0.073649
O 4.163126 0.096973 -0.583138
H 3.179542 1.781726 0.005516

Glyceric acid (1A/C1)

C 0.212464 0.210696 0.384934
H 0.338692 0.074970 1.471346
C 1.221935 -0.707134 -0.317758
H 1.082070 -0.640780 -1.404559
H 1.071571 -1.740530 0.010008
O -2.054286 0.743540 -0.253545
H -2.922069 0.324099 -0.398497
O 0.402556 1.566473 0.023243
H 1.358678 1.723585 0.081262
C -1.207605 -0.254585 0.076433
O -1.548203 -1.424720 0.149587
O 2.514791 -0.209600 0.062532
H 3.191426 -0.640750 -0.475739

Mesoxalic acid (1A/C1)

C 1.280443 -0.231905 0.166168
C -0.000068 0.609544 0.000118
C -1.280403 -0.232120 -0.166093
O -2.318726 0.261911 0.528561
H -3.094973 -0.294427 0.329813
O 2.318307 0.261866 -0.529372
H 3.094737 -0.294251 -0.330722
O 1.309876 -1.189174 0.912564
O -0.000128 1.819713 0.000129
O -1.309278 -1.189871 -0.911913

3-hydroxypropanoic acid (1A/C1)

C -1.319415 0.335735 -0.314506
H -1.204167 1.377142 0.008016
H -1.198575 0.295893 -1.406448
C -0.261801 -0.543488 0.360154
H -0.389569 -1.586520 0.068350
H -0.392992 -0.477920 1.446575
C 1.163564 -0.146422 0.041382
O 2.062291 -0.910171 -0.260565
O 1.365841 1.201909 0.150639
H 2.307287 1.353538 -0.049078
O -2.594130 -0.190306 0.076576

26
 H -3.288087 0.351458 -0.322800

1,4-sorbitan (1A/C1)
C -1.798301 1.314011 -0.354083
O -0.654325 1.708713 0.453376
C 0.175136 0.558400 0.733485
C -0.829980 -0.611785 0.681265
C -1.734352 -0.211010 -0.497441
H -1.758148 1.839481 -1.313079
H 0.582934 0.700608 1.740037
H -2.712900 1.599349 0.173960
H -1.444390 -0.545370 1.586134
H -1.252894 -0.502811 -1.441733
O -3.044640 -0.765179 -0.430934
H -2.948916 -1.729621 -0.413496
O -0.346380 -1.940489 0.636909
H 0.449420 -1.988212 0.069193
C 1.355616 0.579726 -0.266757
C 2.473885 -0.428167 0.005316
H 3.387034 -0.045468 -0.461026
H 2.643843 -0.543807 1.083134
O 2.099257 -1.689378 -0.593905
H 2.780660 -2.346435 -0.395996
O 1.970293 1.867879 -0.195342
H 1.242161 2.506697 -0.111621
H 0.985537 0.396168 -1.287043

2,5-anhydrosugars (1A/C2)
C -0.348010 -1.122831 0.599891
O 0.000000 0.000000 1.431900
C 0.348010 1.122831 0.599891
C -0.068368 0.759903 -0.838644
C 0.068368 -0.759903 -0.838644
H -1.435780 -1.275837 0.619649
H 1.435780 1.275837 0.619649
H -1.126545 1.010661 -1.002932
H 1.126545 -1.010661 -1.002932
O 0.751612 1.363767 -1.829227
H 0.670194 2.323028 -1.709498
O -0.751612 -1.363767 -1.829227
H -0.670194 -2.323028 -1.709498
C -0.342102 2.373391 1.133376
H 0.005297 2.594064 2.150497
H -1.427403 2.207380 1.157779
C 0.342102 -2.373391 1.133376
H -0.005297 -2.594064 2.150497

27
 H 1.427403 -2.207380 1.157779
O 0.000000 3.438572 0.225847
H -0.431158 4.252681 0.516197
O 0.000000 -3.438572 0.225847
H 0.431158 -4.252681 0.516197

Isosorbide (1A/C2)
C 0.041270 1.796782 0.052975
C -0.041270 -1.796782 0.052975
H -0.700581 2.420858 0.564546
H 0.700581 -2.420858 0.564546
O -1.561602 -0.010900 0.462032
O 1.561602 0.010900 0.462032
O 0.587315 2.463051 -1.091640
H 1.121454 3.211231 -0.792184
O -0.587315 -2.463051 -1.091640
H -1.121454 -3.211231 -0.792184
C -1.110400 -1.260077 1.011633
H -0.675726 -1.102941 2.009363
H -1.976304 -1.923803 1.106601
C 1.110400 1.260077 1.011633
H 0.675726 1.102941 2.009363
H 1.976304 1.923803 1.106601
C 0.587315 -0.496772 -0.465777
H 1.050628 -0.638817 -1.444448
C -0.587315 0.496772 -0.465777
H -1.050628 0.638817 -1.444448

Ethylene glycol (1Ag/C2h)

C 0.439895 0.622332 0.000000
C -0.439895 -0.622332 0.000000
H 1.082012 0.612372 0.891054
H 1.082012 0.612372 -0.891054
H -1.082012 -0.612372 0.891054
H -1.082012 -0.612372 -0.891054
O -0.439895 1.755310 0.000000
H 0.094284 2.560326 0.000000
O 0.439895 -1.755310 0.000000
H -0.094284 -2.560326 0.000000

Levulinic acid (1A′/Cs)

C -1.387802 -1.383334 0.000000
O -2.434490 -0.757727 0.000000
O -1.357971 -2.747181 0.000000
H -2.286007 -3.043479 0.000000
C 0.007108 -0.797275 0.000000

28
 C 0.000000 0.729710 0.000000
H 0.544579 -1.190647 0.868310
H -0.546655 1.115951 0.868327
C 1.398249 1.335709 0.000000
O 2.406748 0.640195 0.000000
C 1.472654 2.852548 0.000000
H 0.959963 3.256471 -0.880160
H 0.959963 3.256471 0.880160
H 2.514688 3.173470 0.000000
H 0.544579 -1.190647 -0.868310
H -0.546655 1.115951 -0.868327

Propanol (1A′/Cs)
C 0.093752 -0.777137 0.000000
C 0.000000 0.745569 0.000000
H -0.412669 -1.182397 0.889403
H -0.412669 -1.182397 -0.889403
C -1.454320 1.240098 0.000000
H 0.530436 1.126711 0.879738
H 0.530436 1.126711 -0.879738
H -1.494493 2.333663 0.000000
H -1.996384 0.887810 -0.884998
H -1.996384 0.887810 0.884998
O 1.483064 -1.142753 0.000000
H 1.550621 -2.107069 0.000000

α-amino-glyceric acid (1A/C1)

C 0.996377 -0.268659 0.017180
O 0.837524 -1.350659 -0.533993
O 2.220775 0.205062 0.343173
H 2.871997 -0.441815 0.014175
C -0.134540 0.690512 0.396889
H 0.215531 1.287293 1.244345
C -1.386780 -0.109833 0.816577
H -1.137513 -0.787594 1.646755
H -2.150606 0.590539 1.168590
O -1.965170 -0.821580 -0.274138
H -1.284855 -1.439181 -0.593653
N -0.337161 1.583709 -0.754049
H -0.964010 1.126080 -1.414147
H -0.785793 2.444018 -0.451926

1,3-propandiol (1A1/C2v)
C 0.000000 1.266627 -0.487108
H -0.889756 1.287294 -1.135105
H 0.889756 1.287294 -1.135105

29
 C 0.000000 0.000000 0.364460
H 0.882238 0.000000 1.012666
H -0.882238 0.000000 1.012666
C 0.000000 -1.266627 -0.487108
H 0.889756 -1.287294 -1.135105
H -0.889756 -1.287294 -1.135105
O 0.000000 -2.393727 0.401567
H 0.000000 -3.203799 -0.125722
O 0.000000 2.393727 0.401567
H 0.000000 3.203799 -0.125722

3-hydroxy-propanal (1A/C1)
C -0.586620 0.457617 0.282917
H -0.426856 1.410099 -0.241133
H -0.843993 0.682330 1.330124
C 0.672936 -0.363952 0.249610
H 0.585167 -1.372256 0.651892
C 1.848355 0.077371 -0.215488
H 1.957746 1.073916 -0.636280
H 2.735877 -0.548720 -0.187366
O -1.642031 -0.303094 -0.330857
H -2.479721 0.153173 -0.172616

Pyruvaldehyde (1A′/Cs)
C 1.278459 1.286150 0.000000
C 0.000000 0.476415 0.000000
H 1.048003 2.351226 0.000000
H 1.881788 1.034568 0.880782
H 1.881788 1.034568 -0.880782
C 0.190761 -1.070132 0.000000
O -1.119469 0.952986 0.000000
O -0.739582 -1.846936 0.000000
H 1.245508 -1.423351 0.000000

Glycidol (1A/C1)
C -1.679094 0.447728 0.016112
C -0.340572 0.018801 0.469165
O -1.166055 -0.855634 -0.325993
H -2.507357 0.451055 0.723103
H -1.767410 1.140627 -0.820463
H -0.220089 -0.305875 1.502833
C 0.910320 0.564552 -0.172651
H 1.132282 1.551278 0.263880
H 0.732995 0.685902 -1.249714
O 1.979604 -0.354060 0.083684
H 2.777273 -0.031917 -0.356923

30
Glyceric acid (1A/C1)
C -1.207553 -0.254784 0.076052
O -1.547129 -1.425332 0.147604
O -2.055492 0.743259 -0.250793
H -2.923110 0.323378 -0.395431
C 0.212355 0.211251 0.384166
H 0.338159 0.077070 1.470881
C 1.222399 -0.707368 -0.316629
H 1.072210 -1.740311 0.012553
H 1.083073 -0.642725 -1.403600
O 2.514943 -0.208887 0.063530
H 3.191916 -0.640578 -0.473881
O 0.402219 1.566517 0.020724
H 1.358213 1.724117 0.079418

Glycolic acid (1A/C1)

C -0.610706 -0.106707 0.001969
O -1.643455 -0.740433 -0.093372
O -0.572793 1.255437 0.051104
H -1.493419 1.567771 -0.010383
C 0.774938 -0.726338 0.143310
H 0.834887 -1.106667 1.175374
H 0.818899 -1.588630 -0.524911
O 1.860766 0.126270 -0.174136
H 1.698105 0.995601 0.219470

Glyoxalic acid (1A′/Cs)

C 0.000000 0.540857 0.000000
O -0.623384 1.586659 0.000000
O 1.340722 0.430732 0.000000
H 1.705065 1.334650 0.000000
C -0.724560 -0.817686 0.000000
H -1.824488 -0.700860 0.000000
O -0.158990 -1.888993 0.000000

Tartronic acid (1A/C1)

C 1.235781 -0.253202 -0.011528
O 2.068429 0.399844 0.588799
O 1.277572 -1.591691 -0.167822
H 2.071636 -1.917444 0.294286
C 0.009254 0.382477 -0.677931
H -0.033506 0.055802 -1.720830
C -1.278788 -0.152328 -0.016166
O -2.083200 -0.875479 -0.565809
O -1.401214 0.291751 1.258911

31
 H -2.242294 -0.057890 1.604246
O 0.094478 1.782888 -0.615060
H 0.758164 1.999346 0.063906

Triketo (1A1/C2v)
C 0.000000 1.317908 -0.624736
O 0.000000 2.406802 -0.092392
H 0.000000 1.208867 -1.729291
C 0.000000 0.000000 0.195641
O 0.000000 0.000000 1.407481
C 0.000000 -1.317908 -0.624736
O 0.000000 -2.406802 -0.092392
H 0.000000 -1.208867 -1.729291

Oxalic acid (1Ag/C2h)

C -0.074893 0.770708 0.000000
O -1.137749 1.352720 0.000000
O 1.137749 1.357819 0.000000
H 0.985044 2.320207 0.000000
C 0.074893 -0.770708 0.000000
O 1.137749 -1.352720 0.000000
O -1.137749 -1.357819 0.000000
H -0.985044 -2.320207 0.000000

Hydroxymethyl glyoxal (1A′/Cs)

C -1.539679 0.439574 0.000000
O -2.179956 -0.596157 0.000000
H -2.008058 1.444134 0.000000
C 0.000000 0.484983 0.000000
O 0.547529 1.572604 0.000000
C 0.705791 -0.857318 0.000000
H 0.347063 -1.412562 0.881549
H 0.347063 -1.412562 -0.881549
O 2.105304 -0.663086 0.000000
H 2.534237 -1.529344 0.000000

Hydroxypyruvic acid (1A′/Cs)

C 0.000000 0.436263 0.000000
O 0.469668 1.552437 0.000000
C 0.904985 -0.825094 0.000000
O 0.457052 -1.959214 0.000000
O -2.229719 1.305663 0.000000
H -3.169177 1.078210 0.000000
C -1.482900 0.105778 0.000000
H -1.678841 -0.524033 0.881720
H -1.678841 -0.524033 -0.881720

32
 O 2.214331 -0.519981 0.000000
H 2.703695 -1.363069 0.000000

Formic acid (1A′/Cs)

C 0.000000 0.424867 0.000000
O 1.171232 0.110324 0.000000
O -1.040644 -0.443147 0.000000
H -0.377923 1.457416 0.000000
H -0.666785 -1.344029 0.000000

Diglyceraldehyde (1A′/Cs)
C 0.772513 0.056190 3.644480
C -0.077957 -0.202786 2.397948
H 1.783524 -0.349653 3.500662
H 0.839002 1.137350 3.830090
C 0.494293 0.514363 1.181006
H -0.075095 -1.283357 2.193714
H 0.158126 1.561898 1.195639
H 1.597722 0.505041 1.225624
C 0.494293 0.514363 -1.181006
C -0.077957 -0.202786 -2.397948
H 1.597722 0.505041 -1.225624
H 0.158126 1.561898 -1.195639
C 0.772513 0.056190 -3.644480
H -0.075095 -1.283357 -2.193714
H 0.839002 1.137350 -3.830090
H 1.783524 -0.349653 -3.500662
O -1.413955 0.254271 2.607985
H -1.706020 -0.129717 3.449344
O -1.413955 0.254271 -2.607985
H -1.706020 -0.129717 -3.449344
O 0.111905 -0.605505 4.736254
H 0.476807 -0.284616 5.570968
O 0.111905 -0.605505 -4.736254
H 0.476807 -0.284616 -5.570968
O 0.052310 -0.138419 0.000000

δ-aminolevulinate (1A/C1)
C -2.463888 0.131176 -0.024496
O -2.674806 1.297315 -0.310861
O -3.474038 -0.757902 0.196184
H -4.306235 -0.268375 0.066131
C -1.106977 -0.523206 0.121265
C 0.039002 0.483900 0.043181
H -1.008771 -1.277636 -0.665868
H -1.091348 -1.082586 1.061599

33
 H -0.062296 1.099039 -0.859457
H 0.005267 1.194210 0.876843
C 1.408051 -0.174379 -0.006434
O 1.558321 -1.366291 -0.247432
C 2.602441 0.730533 0.269932
H 2.425855 1.699944 -0.214951
H 2.568779 0.925263 1.357865
N 3.846914 0.130014 -0.195286
H 4.634003 0.410666 0.379916
H 3.758758 -0.883745 -0.158883

1,4-pentanediol (1A/C1)
C 1.609491 0.068964 -0.328688
C 0.312486 -0.582023 0.156391
H 1.537931 0.225571 -1.416988
C -0.948223 0.191635 -0.255019
H 0.271319 -1.603911 -0.241741
H 0.365192 -0.664926 1.249719
C -2.221501 -0.455849 0.278612
H -0.888672 1.219385 0.113195
H -1.017024 0.243168 -1.348626
H -2.293307 -1.496932 -0.073445
H -2.199181 -0.473219 1.378814
O 1.701649 1.350645 0.325301
H 2.499418 1.798044 0.011353
O -3.344967 0.308372 -0.189835
H -4.153575 -0.080340 0.169821
C 2.841180 -0.791704 -0.028690
H 2.774847 -1.759285 -0.538090
H 3.758170 -0.298020 -0.371407
H 2.930838 -0.967803 1.048024

Angelilactone I (1A/C1)
C -1.205785 -0.176803 -0.024835
C -0.774078 1.241280 -0.157294
C 0.533256 1.315995 0.122972
O -0.099126 -0.917434 0.337496
H -1.459654 2.028198 -0.440360
H 1.161979 2.199442 0.118540
C 1.055700 -0.058711 0.456577
H 1.383033 -0.100777 1.504270
C 2.180980 -0.554525 -0.455163
H 3.064964 0.080463 -0.336957
H 2.450340 -1.579988 -0.190611
H 1.865695 -0.531478 -1.501534
O -2.301723 -0.669976 -0.188357

34
Angelilactone II (1A′/Cs)
C -1.039161 -0.023542 0.000000
C -0.587642 -1.285329 0.000000
C 1.212440 0.245797 0.000000
O 0.000000 0.923617 0.000000
H -1.204710 -2.172755 0.000000
C -2.411252 0.559257 0.000000
H -2.561614 1.188919 0.883279
H -2.561614 1.188919 -0.883279
H -3.156706 -0.238456 0.000000
O 2.270970 0.825939 0.000000
C 0.917955 -1.253157 0.000000
H 1.381423 -1.710620 0.881256
H 1.381423 -1.710620 -0.881256

β-acetylacrylic acid (1A′/Cs)

C 1.249782 -1.486151 0.000000
O 2.377836 -1.019393 0.000000
O 1.006155 -2.826959 0.000000
H 1.875216 -3.267408 0.000000
C -0.018992 -0.707190 0.000000
C 0.000000 0.635448 0.000000
H -0.958601 -1.250944 0.000000
H 0.953934 1.157736 0.000000
C -1.269683 1.441024 0.000000
O -2.370741 0.900383 0.000000
C -1.101730 2.946627 0.000000
H -0.527831 3.258376 0.880565
H -0.527831 3.258376 -0.880565
H -2.077149 3.433072 0.000000

Valeric acid(1A′/Cs)
C -1.513120 0.848815 0.000000
O -2.283123 -0.095149 0.000000
O -1.955257 2.143114 0.000000
H -2.928350 2.098691 0.000000
C 0.000000 0.778727 0.000000
C 0.548240 -0.651655 0.000000
H 0.351589 1.341635 0.873271
H 0.351589 1.341635 -0.873271
C 2.082625 -0.690379 0.000000
H 0.161652 -1.186361 0.874720
H 0.161652 -1.186361 -0.874720
C 2.639496 -2.121635 0.000000
H 2.462019 -0.151036 -0.877969

35
 H 2.462019 -0.151036 0.877969
H 3.734240 -2.123044 0.000000
H 2.303592 -2.675541 0.883776
H 2.303592 -2.675541 -0.883776

5-nonanone (1A1/C2v)
C 0.000000 1.295236 -0.604293
C 0.000000 2.571698 0.240966
H -0.872137 1.270156 -1.272817
H 0.872137 1.270156 -1.272817
C 0.000000 3.849115 -0.610716
H -0.873350 2.564878 0.902784
H 0.873350 2.564878 0.902784
C 0.000000 5.129297 0.237702
H 0.877865 3.849482 -1.270673
H -0.877865 3.849482 -1.270673
H 0.000000 6.025733 -0.391019
H -0.883643 5.173238 0.884239
H 0.883643 5.173238 0.884239
C 0.000000 0.000000 0.203151
C 0.000000 -1.295236 -0.604293
C 0.000000 -2.571698 0.240966
H -0.872137 -1.270156 -1.272817
H 0.872137 -1.270156 -1.272817
C 0.000000 -3.849115 -0.610716
H 0.873350 -2.564878 0.902784
H -0.873350 -2.564878 0.902784
H -0.877865 -3.849482 -1.270673
H 0.877865 -3.849482 -1.270673
C 0.000000 -5.129297 0.237702
H -0.883643 -5.173238 0.884239
H 0.000000 -6.025733 -0.391019
H 0.883643 -5.173238 0.884239
O 0.000000 0.000000 1.428139

4-methyl-octane (1A/C1)
C 0.570595 0.348867 -0.197086
C 1.842160 -0.419499 0.220478
H 0.531731 0.352679 -1.296923
C 3.156169 0.091572 -0.391457
H 1.925507 -0.406268 1.316906
H 1.718993 -1.474274 -0.060960
C 4.361895 -0.784520 -0.018225
H 3.056607 0.126179 -1.484611
H 3.349136 1.120216 -0.066593
H 5.286707 -0.402578 -0.463530

36
 H 4.504144 -0.817918 1.068094
H 4.224999 -1.815263 -0.364739
C -0.684298 -0.392948 0.310005
C -2.027062 0.149280 -0.204337
H -0.686047 -0.381466 1.409507
H -0.603212 -1.448959 0.018297
C -3.228412 -0.699564 0.239332
H -2.178253 1.179118 0.141508
H -2.004245 0.193701 -1.302333
C -4.572391 -0.152714 -0.264722
H -3.096538 -1.729475 -0.117171
H -3.246020 -0.755650 1.335657
H -5.408295 -0.778477 0.065583
H -4.749479 0.863356 0.106188
H -4.597285 -0.113429 -1.359805
C 0.603670 1.812684 0.279181
H -0.283008 2.363484 -0.047337
H 0.644120 1.862286 1.374576
H 1.476483 2.343785 -0.111322

3,4-dimethyl-septane (1A/C1)
C 0.166967 0.428136 -0.295195
C 1.426985 -0.184738 0.362040
H 0.239497 0.264092 -1.381267
C 2.743460 0.086830 -0.384219
H 1.507694 0.198364 1.389371
H 1.313461 -1.270196 0.454795
C 3.961647 -0.536474 0.314232
H 2.665622 -0.312799 -1.403855
H 2.906098 1.165764 -0.489786
H 4.885127 -0.337786 -0.239947
H 4.086283 -0.133101 1.325687
H 3.853537 -1.623553 0.403749
C -1.128978 -0.290777 0.186876
C -2.416895 0.494222 -0.147635
H -1.070680 -0.367854 1.284068
C -3.715959 -0.152974 0.360686
H -2.351402 1.497156 0.284177
H -2.481585 0.630495 -1.236507
H -3.933238 -1.101324 -0.139276
H -3.663651 -0.348231 1.438481
C 0.147805 1.950418 -0.052934
H -0.611912 2.458627 -0.652024
H -0.047429 2.176124 1.002647
H 1.112809 2.396676 -0.310905
H -4.569527 0.511014 0.187089

37
C -1.208864 -1.718669 -0.390550
H -1.380888 -1.683457 -1.473521
H -0.290372 -2.286268 -0.220488
H -2.026450 -2.289589 0.057702

38