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1 Supplementary Information Indigo carmine: An organic crystal as a positive-electrode material for rechargeable sodium batteries Masaru Yao*, Kentaro Kuratani, Toshikatsu Kojima, Nobuhiko Takeichi, Hiroshi Senoh, and Tetsu Kiyobayashi Research Institute for Ubiquitous Energy Devices, National Institute of Advanced Industrial Science and Technology (AIST) Midorigaoka, Ikeda, Osaka , Japan * Corresponding author Tel: Fax: m.yao@aist.go.jp
2 Discharge capacity, Potential, V vs. Na + /Na a 3 2 Intensity 1 st -5 th 1 2 nd -5 th 1 st Capacity, mah g (IC) 1 b mah g (IC) Efficiency, % Cycle number Figure S1 Charge/discharge performance of a conductive-additive-reduced IC-electrode. a, Charge/discharge curves. b, Cycle-life performance. Composition: IC:AB:PTFE=7:25:5, Current density: 2 ma g 1, Potential range: V vs. Na + /Na, Temperature: 3 o C. Observed Calculated Difference θ, deg. (Cu Kα) Figure S2 Powder XRD pattern and the profile fitting results of the polymorphic form of IC. Crystallographic parameters, Formula: C 16H 8N 2Na 2O 8S 2, M: , Crystal system: monoclinic, Space group: P2 1/c, a: (6) Å, b: 8.277(4) Å, c: (2) Å, β: (2) o, V: (6) Å 3, Z: 2, T: 298 K, D calc: 1.78 g cm 3, R wp: 6.1%, S: 1.17.
3 Intensity b a c Figure S3 Crystal structure of indigo. S1 Hydrogen atoms are omitted for clarity. Crystal structure data, Formula: C 16H 1N 2O 2, Crystal system: monoclinic, Space group: P2 1/c, a= 9.24 Å, b= 5.77 Å, c= Å, β= 117. o, Z=2, D calc= 1.5 g cm 3, R= 5.1 %. Reference: [S1] Süsse, P., Steins, M., & Kupcik, V. Indigo: crystal structure refinement based on synchrotron data. Z. Kristallogr. 184, (1988). Observed Calculated Difference θ, deg. (Cu Kα) Figure S4 Powder XRD pattern and the profile fitting results of the original form of IC. Calculated pattern: crystal system: orthorhombic, a: 17.6 Å, b: 31. Å, c: 6.75 Å. In this analysis, we could not determine the space group. The assumed cell parameters might be wrong.
4 Discharge capacity, Potential, V vs. Na + /Na a 3 1 st 2 nd 3 rd nd 3 rd 1 st Capacity, mah g (IC) 1 b mah g (IC) Cycle number Efficiency, % Figure S5 Charge/discharge performance of the electrode using the polymorphic form of IC in the sodium system. a, Charge/discharge curves in the sodium system. Current density: 1 ma g 1, Temperature: 3 o C. b, Cycle-life performance in the sodium system. Current density: 2 ma g 1, Potential range: V vs. Na + /Na, Temperature: 3 o C.
5 Crystallographic data (cif format) data_global _audit_creation_date ' ' _audit_creation_method 'PDXL Version (Rigaku, 212)' _audit_conform_dict_name _audit_conform_dict_version _audit_conform_dict_location cif_core.dic ftp://ftp.iucr.org/pub/cif_core.dic cif_pd.dic 1..1 ftp://ftp.iucr.org/pub/cif_pd.dic # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic? _journal_date_from_coeditor? _journal_date_accepted? _journal_coeditor_code? # SUBMISSION DETAILS _publ_contact_author_name 'Masaru YAO' _publ_contact_author_address Research Institute for Ubiquitous Energy Devices, National Institute of Advanced Industrial Science and Technology (AIST) Midorigaoka, Ikeda, Osaka , Japan _publ_contact_author_fax ' ' _publ_contact_author_ 'm.yao@aist.go.jp' _publ_contact_author_phone ' ' _publ_contact_letter ENTER TEXT OF LETTER _journal_name_full 'Scientific Reports' _publ_requested_category? _publ_requested_coeditor_name? # TITLE AND AUTHOR LIST _publ_section_title Indigo carmine: An organic crystal as a positive-electrode material for rechargeable sodium batteries _publ_section_title_footnote ENTER FOOTNOTE TO TITLE OF PAPER _publ_author_name 'Masaru YAO' _publ_author_footnote _publ_author_address FIRST AUTHORS FOOTNOTES FIRST AUTHORS ADDRESS # TEXT _publ_section_synopsis ENTER SYNOPSIS _publ_section_abstract ENTER ABSTRACT _publ_section_comment ENTER TEXT
6 _publ_section_acknowledgements ENTER ACKNOWLEDGEMENTS _publ_section_references ENTER OTHER REFERENCES PDXL Version (212). Integrated X-ray Powder Diffraction Software. Rigaku Corporation, Tokyo , Japan. _publ_section_figure_captions ENTER FIGURE CAPTIONS _publ_section_exptl_prep ENTER COMPOUND PREPARATION DETAILS _publ_section_exptl_refinement ENTER SPECIAL DETAILS OF THE REFINEMENT data_indigocarmine # CHEMICAL DATA _chemical_name_systematic 5,5'-indigodisulfonic acid sodium salt _chemical_name_common 'Indigo carmine' _chemical_formula_structural 'C16 H8 N2 Na2 O8 S2' _chemical_formula_moiety '(Na +)2, C16 H8 N2 O8 S2 2-' _chemical_formula_sum 'C16 H8 N2 Na2 O8 S2' _chemical_formula_weight _chemical_melting_point? _chemical_compound_source? # CRYSTAL DATA _space_group_crystal_system monoclinic _space_group_name_h-m_alt 'P 1 21/c 1' _space_group_name_hall '-P 2ybc' _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 'x,y,z' 2 'x,1/2-y,1/2+z' 3 '-x,-y,-z' 4 '-x,-1/2+y,-1/2-z' _cell_length_a (6) _cell_length_b 8.277(4) _cell_length_c (2) _cell_angle_alpha 9 _cell_angle_beta (2) _cell_angle_gamma 9 _cell_volume (6) _cell_formula_units_z 2 _cell_measurement_temperature 298 _rigaku_reference_intensity_ratio 1.62 _pd_char_colour 'dark-blue' _exptl_crystal_density_diffrn 1.78 _exptl_crystal_f_ 472. # EXPERIMENTAL DATA _computing_data_collection 'Rigaku SmartLab' _diffrn_measurement_device_type 'Rigaku SmartLabGuidance' _diffrn_radiation_type 'Cu K a~1~' _diffrn_radiation_wavelength _diffrn_measurement_method 2 q _diffrn_ambient_temperature 298 _pd_meas_2theta_range_min 3. _pd_meas_2theta_range_max 9.
7 _pd_meas_2theta_range_inc.5 _pd_meas_number_of_points 1741 _reflns_number_total 73 _reflns_limit_h_min _reflns_limit_h_max 16 _reflns_limit_k_min _reflns_limit_k_max 7 _reflns_limit_l_min -5 _reflns_limit_l_max 5 _reflns_d_resolution_high 1.92 _reflns_d_resolution_low # REFINEMENT DATA _computing_cell_refinement 'PDXL Version (Rigaku, 212)' _computing_structure_solution 'PDXL Version (Rigaku, 212)' _computing_structure_refinement 'PDXL Version (Rigaku, 212)' _computing_publication_material 'PDXL Version (Rigaku, 212)' _computing_molecular_graphics '?' _refine_special_details _pd_calc_method 'Rietveld Refinement' _refine_ls_weighting_scheme sigma _refine_ls_structure_factor_coef Fsqd _refine_ls_hydrogen_treatment mixed _refine_ls_number_restraints 51 _refine_ls_number_constraints 1 _refine_ls_number_parameters 114 _refine_ls_matrix_type full _pd_proc_ls_pref_orient_corr Spherical harmonics Maximum harmonic order: 6 _pd_proc_ls_prof_r_factor.439 _pd_proc_ls_prof_wr_expected.512 _pd_proc_ls_prof_wr_factor.61 _refine_ls_goodness_of_fit_all _refine_ls_shift/su_max.19 _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_cromer_mann_a1 _atom_type_scat_cromer_mann_b1 _atom_type_scat_cromer_mann_a2 _atom_type_scat_cromer_mann_b2 _atom_type_scat_cromer_mann_a3 _atom_type_scat_cromer_mann_b3 _atom_type_scat_cromer_mann_a4 _atom_type_scat_cromer_mann_b4 _atom_type_scat_cromer_mann_c _atom_type_scat_source 'C' 'C' 'H' 'H' International Tables for Crystallography Vol. C, Table (1999). 'N' 'N' 'Na' 'Na'
8 'O' 'O' 'S' 'S' # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_u_iso_or_equiv _atom_site_adp_type _atom_site_occupancy S1 S.127(12).5129(5).4123(5).11(13) Uiso 1 Na1 Na.231(3).182(8).3697(1).11(13) Uiso 1 O1 O.4182(2).432(11).8128(9).11(13) Uiso 1 O2 O.62(3).4418(9).221(8).11(13) Uiso 1 O3 O.797(3).689(7).4488(12).11(13) Uiso 1 O4 O.121(3).488(9).642(9).11(13) Uiso 1 N1 N.42578(19).5487(8).2681(9).11(13) Uiso 1 C1 C.46231(16).563(9).47(1).11(13) Uiso 1 C2 C.444(14).4741(8).6171(8).11(13) Uiso 1 C3 C.33187(14).58(6).4836(7).11(13) Uiso 1 C4 C.2576(2).4886(7).5279(7).11(13) Uiso 1 C5 C.19954(17).5235(6).3622(7).11(13) Uiso 1 C6 C.2174(2).568(8).1555(8).11(13) Uiso 1 C7 C.2913(2).5792(9).184(8).11(13) Uiso 1 C8 C.3487(15).546(7).2738(7).11(13) Uiso 1 H1 H.4477(3).5728(11).1555(12).11(13) Uiso 1 H2 H.2468(3).4598(9).6669(1).11(13) Uiso 1 H3 H.178(3).599(11).454(11).11(13) Uiso 1 H4 H.32(3).694(13) -.298(11).11(13) Uiso 1 # MOLECULAR GEOMETRY _geom_special_details ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 S1 O (6) yes.. S1 O (7) yes.. S1 O (7) yes.. S1 C (4) yes.. O1 C (8) yes.. N1 C (7) yes.. N1 C (4) yes.. C1 C (4) yes. 3_666 C1 C (6) yes.. C2 C (4) yes.. C3 C (5) yes.. C3 C8 1.47(6) yes.. C4 C (5) yes.. C5 C (7) yes.. C6 C (6) yes.. C7 C (6) yes.. N1 H1.859(9) no.. C4 H2.93(8) no.. C6 H3.929(7) no..
9 C7 H4.927(9) no.. _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 S1 C5 C6 12.3(4) yes... S1 C5 C4 12.2(4) yes... O2 S1 O (5) yes... O2 S1 O (6) yes... O3 S1 O (5) yes... O2 S1 C5 16.9(4) yes... O3 S1 C5 16.3(4) yes... O4 S1 C5 16.(3) yes... O1 C2 C3 13.2(4) yes... O1 C2 C (3) yes... N1 C1 C (6) yes.. 3_666 N1 C1 C2 18.3(3) yes... N1 C8 C3 11.3(4) yes... N1 C8 C (6) yes... C1 N1 C8 19.3(5) yes... C2 C3 C (5) yes... C2 C3 C8 17.(3) yes... C4 C3 C8 12.7(4) yes... C3 C4 C (5) yes... C4 C5 C (4) yes... C5 C6 C (5) yes... C6 C7 C (5) yes... C1 C1 C (6) yes 3_666.. C1 C2 C3 15.1(5) yes... C3 C8 C (4) yes... C8 N1 H (8) no... C1 N1 H (6) no... C5 C6 H (7) no... C7 C6 H (8) no... C6 C7 H (7) no... C8 C7 H (7) no... C3 C4 H2 12.8(6) no... C5 C4 H2 12.7(6) no...
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