Supplemental Information for

Unique Complexation Behavior of Alkali Metal Ions and 2-Pyrone-4,6-Dicarboxylic Acid (PDC) obtained from a Metabolic Intermediate of Lignin

Masami Bito,1Yuichiro Otsuka,2 Masaya Nakamura,2Eiji Masai,3 Yoshihiro Katayama,4Kiyotaka Shigehara,5 and Kazuhiro Shikinaka6*

1J-CHEMICAL, INC., Chuo-ku, Tokyo 104-0044

2Forestry and Forest Products Research Institute, Tsukuba, Ibaraki 305-8687

3Department of Bioengineering, Nagaoka University of Technology, Nagaoka, Niigata 940-2188

4College of Bioresource Science, NihonUniversity, Fujisawa, Kanagawa 252-0880

5Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588

6Research Institute for Chemical Process Technology, National Institute of Advanced Industrial Science, Sendai, Miyagi 983-8551, Japan

Table S1 Crystal data and structure refinement forthe complexes of PDC withLiion

Empirical Formula / C14H15Li1O16
Formula Weight / 446.20
Crystal System / Triclinic
Lattice Type / Primitive
Lattice Parameters / a = 9.924(7) Å
b =10.069(7) Å
c =10.365(7) Å
a =111.349(7) o
b = 104.111(3) o
g =100.042(8) o
V = 895.0(11) Å3
Space Group / P-1 (#2)
Z value / 2
Densitycalc / 1.656 g/cm3
F000 / 460.00
m(MoKα) / 1.544 cm-1
Refinement Method / Full-matrix least-squares on F2
Function Minimized / S w (Fo2 - Fc2)2
Least Squares Weights / 1/[0.0286Fo2+1.0000s(Fo2)]/(4Fo2)
Reflection/Parameter Ratio / 14.62
Residuals: R1 (I>2.00s(I)) / 0.0944
Residuals: R (All reflections) / 0.1523
Residuals: wR2 (All reflections) / 0.3162
Goodness of Fit Indicator / 1.035
Max Shift/Error in Final Cycle / 0.000
Maximum peak in Final Diff. Map / 0.88 e/Å3
Minimum peak in Final Diff. Map / -0.72 e/Å3

Table S2 Crystal data and structure refinement forthe complexes of PDC withRbion

Empirical Formula / C14H8Rb2O13.5
Formula Weight / 563.14
Crystal System / Monoclinic
Lattice Type / Primitive
Lattice Parameters / a = 4.534(3) Å
b =26.526(3) Å
c =13.968(2) Å
a =90.00o
b = 95.890(7) o
g =90.00o
V = 1671.0(3) Å3
Space Group / P21/n (#14)
Z value / 4
Densitycalc / 2.238 g/cm3
F000 / 318.00
m(MoKα) / 59.18 cm-1
Refinement Method / Full-matrix least-squares on F2
Function Minimized / S w (Fo2 - Fc2)2
Least Squares Weights / 1/[0.0286Fo2+1.0000s(Fo2)]/(4Fo2)
Reflection/Parameter Ratio / 18.62
Residuals: R1 (I>2.00s(I)) / 0.1172
Residuals: R (All reflections) / 0.0566
Residuals: wR2 (All reflections) / 0.1119
Goodness of Fit Indicator / 1.012
Max Shift/Error in Final Cycle / 0.003
Maximum peak in Final Diff. Map / 1.012 e/Å3
Minimum peak in Final Diff. Map / -0.937 e/Å3

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