4 Table S3. Bond lengths [Å] and angles [deg] for

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1 Supporting Information: "Inverse Sodium Hydride": A Crystalline Salt that Contains H + and Na. Mikhail Y. Redko, Mircea Vlassa, James E. Jackson, Andrzej W. Misiolek, Rui H. Huang, and James L. Dye* Page Contents 2 Table S1. Crystal data and structure refinement for 3 6 AdamanzaneH + Glycolate. 3 Table S2. Atomic coordinates ( x 10 4 ) and equivalent isotropic displacement parameters (Å 2 x 10 3 ), for 3 6 AdamanzaneH + Glycolate. 4 Table S3. Bond lengths [Å] and angles [deg] for 3 6 AdamanzaneH + Glycolate. 5 Table S4. Anisotropic displacement parameters (Å 2 x 10 3 ) for 3 6 AdamanzaneH + Glycolate. 6 Figure 1S. Perspective view (from WebLab Viewer) of the structure of 3 6 AdamanzaneH + Glycolate CIF File - AdzH+Na-.txt 1

2 Table S1. Crystal data and structure refinement for 3 6 AdamanzaneH + Glycolate. Empirical formula: C 20 H 39 N 4 O 3 Formula weight: Temperature: 173(2) K Wavelength: Å Crystal system: orthorhombic Space group: P (No. 19) Unit cell dimensions: a = (18) Å, b = (3) Å, c = (3) Å α = β = γ = 90º, V = (7) Å 3, Z = 4, ρ(calc.) = g cm -3 Absorption coefficient: mm -1, F(000) = 844 Theta range: 1.94º to 28.43º, Index ranges: -11 h 6, -18 k 18, -21 l 20 Reflections collected: Unique: 12941, [R(int) = ]: 4810 Completeness to theta = 28.43: 96.7% Refinement method: Full-matrix least-squares on F 2 Data / restraints / parameters: 4810 / 0 / 248 Goodness-of-fit on F 2 : 3.028, R [I>2σ(I)]: R 1 = , wr 2 = R [all data]: R 1 = , wr 2 = Largest diff. peak and hole: and e.a -3 2

3 Table S2. Atomic coordinates ( x 10 4 ) and equivalent isotropic displacement parameters (Å 2 x 10 3 ), for 3 6 AdamanzaneH + Glycolate. a x y z U(eq) b N(1) 5111(4) 571(2) 2081(2) 22(1) C(2) 6578(6) 667(4) 2511(3) 34(1) C(3) 7585(6) -203(3) 2396(3) 33(1) C(4) 8232(5) -293(3) 1522(3) 30(1) N(5) 7191(3) -592(2) 872(2) 20(1) C(6) 7918(4) -513(3) 68(2) 25(1) C(7) 7970(4) 529(3) -242(3) 27(1) C(8) 6411(5) 922(4) -463(3) 31(1) N(9) 5416(4) 1098(2) 284(2) 19(1) C(10) 3901(6) 1395(4) -31(3) 37(1) C(11) 3081(6) 560(4) -461(3) 40(1) C(12) 2466(7) -98(4) 154(4) 45(1) N(13) 3652(4) -682(3) 624(2) 26(1) C(14) 2982(7) -1099(4) 1342(4) 48(1) C(15) 2718(5) -428(3) 2072(3) 33(1) C(16) 4189(6) -126(4) 2511(3) 38(1) C(17) 4376(6) 1512(3) 2059(3) 34(1) C(18) 5143(5) 2247(3) 1526(3) 29(1) C(19) 6071(6) 1920(3) ` 772(3) 35(1) C(20) 6714(6) -1587(3) 1021(3) 36(1) C(21) 5566(6) -2008(3) 438(3) 37(1) C(22) 4292(6) -1343(4) 30(4) 45(1) O(23) 846(4) 1862(2) 1263(2) 30(1) O(24) -1143(3) 2586(2) 1822(2) 32(1) C(25) 26(4) 2107(3) 1850(2) 22(1) C(26) 449(5) 1740(4) 2730(3) 33(1) O(27) -631(4) 2028(4) 3317(2) 47(1) a All occupancy factors are 1.0. b U(eq) is defined as one third of the trace of the orthogonalized Uij tensors. 3

4 Table S3. Bond lengths [Å] and angles [deg] for 3 6 AdamanzaneH + Glycolate. a N(1)-C(16) 1.453(5) N(1)-C(17) 1.466(5) N(1)-C(2) 1.503(6) C(2)-C(3) 1.524(7) C(3)-C(4) 1.530(6) C(4)-N(5) 1.468(5) N(5)-C(6) 1.457(5) N(5)-C(20) 1.468(5) C(6)-C(7) 1.531(6) C(7)-C(8) 1.554(6) C(8)-N(9) 1.523(5) N(9)-C(19) 1.508(6) N(9)-C(10) 1.518(6) C(10)-C(11) 1.541(7) C(11)-C(12) 1.459(8) C(12)-N(13) 1.542(7) N(13)-C(14) 1.429(7) N(13)-C(22) 1.447(6) C(14)-C(15) 1.519(7) C(15)-C(16) 1.564(7) C(17)-C(18) 1.505(6) C(18)-C(19) 1.544(6) C(20)-C(21) 1.517(7) C(21)-C(22) 1.617(8) O(23)-C(25) 1.249(5) O(24)-C(25) 1.250(5) C(25)-C(26) 1.554(6) C(26)-O(27) 1.417(5) C(16)-N(1)-C(17) 110.1(4) C(16)-N(1)-C(2) 110.3(4) C(17)-N(1)-C(2) 109.4(3) N(1)-C(2)-C(3) 113.6(4) C(2)-C(3)-C(4) 113.9(4) N(5)-C(4)-C(3) 115.7(4) C(6)-N(5)-C(20) 110.5(3) C(6)-N(5)-C(4) 108.8(3) C(20)-N(5)-C(4) 109.8(3) N(5)-C(6)-C(7) 112.1(3) C(6)-C(7)-C(8) 112.3(3) N(9)-C(8)-C(7) 114.3(3) C(19)-N(9)-C(10) 108.9(3) C(19)-N(9)-C(8) 107.5(3) C(10)-N(9)-C(8) 108.2(3) N(9)-C(10)-C(11) 112.3(4) C(12)-C(11)-C(10) 110.5(4) C(11)-C(12)-N(13) 113.4(4) C(14)-N(13)-C(22) 116.5(4) C(14)-N(13)-C(12) 108.4(4) C(22)-N(13)-C(12) 106.7(4) N(13)-C(14)-C(15) 116.3(4) C(14)-C(15)-C(16) 112.4(4) N(1)-C(16)-C(15) 116.9(4) N(1)-C(17)-C(18) 114.2(4) C(17)-C(18)-C(19) 120.0(3) N(9)-C(19)-C(18) 114.8(4) N(5)-C(20)-C(21) 117.6(4) C(20)-C(21)-C(22) 121.2(4) N(13)-C(22)-C(21) 112.3(4) O(23)-C(25)-O(24) 128.4(4) O(23)-C(25)-C(26) 117.1(3) O(24)-C(25)-C(26) 114.5(4) O(27)-C(26)-C(25) 110.3(4) a Symmetry transformations were used to generate equivalent atoms. 4

5 Table S4. Anisotropic displacement parameters (Å 2 x 10 3 ) for 3 6 AdamanzaneH + Glycolate. U 11 U 22 U 33 U 23 U 13 U 12 N(1) 30(2) 18(1) 17(1) -1(1) 5(1) -1(1) C(2) 42(2) 33(2) 29(2) -3(2) -4(2) -2(2) C(3) 41(2) 38(2) 21(2) 4(2) -7(2) 9(2) C(4) 32(2) 29(2) 30(2) 9(2) -4(2) 0(2) N(5) 19(1) 17(1) 24(2) 0(1) 6(1) 1(1) C(6) 22(2) 29(2) 24(2) 0(1) 1(1) 6(2) C(7) 21(2) 32(2) 29(2) 4(2) 13(2) -2(2) C(8) 36(2) 37(2) 21(2) 2(2) 5(2) 4(2) N(9) 22(2) 18(1) 18(1) 1(1) 2(1) 3(1) C(10) 36(2) 41(2) 34(2) -5(2) -3(2) 12(2) C(11) 29(2) 70(3) 22(2) 5(2) -7(2) -12(2) C(12) 41(3) 46(3) 49(3) -2(2) -1(2) -1(2) N(13) 21(2) 28(2) 28(2) -10(1) 7(1) -6(1) C(14) 52(3) 37(3) 56(3) -1(2) 11(3) -10(2) C(15) 39(2) 24(2) 36(2) 2(2) 23(2) -7(2) C(16) 55(3) 37(2) 21(2) 3(2) 6(2) -14(2) C(17) 41(3) 25(2) 36(2) -1(2) 11(2) 0(2) C(18) 49(3) 14(2) 24(2) -3(1) 2(2) 2(2) C(19) 43(3) 30(2) 33(2) 3(2) 2(2) -7(2) C(20) 57(3) 22(2) 28(2) 1(2) 12(2) -8(2) C(21) 41(2) 15(2) 56(3) -12(2) 16(2) -2(2) C(22) 42(3) 45(3) 48(3) -8(2) 4(2) 1(2) O(23) 36(2) 31(2) 23(1) 2(1) 6(1) 7(1) O(24) 27(2) 37(2) 32(2) 9(1) 4(1) 7(1) C(25) 24(2) 18(2) 24(2) -2(1) 0(1) -4(1) C(26) 33(2) 46(3) 21(2) -10(2) 2(2) 12(2) O(27) 42(2) 78(3) 20(2) -9(2) 4(1) 19(2) a The anisotropic displacement factor exponent takes the form: -2 π 2 [ h 2 a* 2 U h k a* b* U 12 ]. 5

6 Figure 1S. Perspective view (from WebLab Viewer) of the structure of 3 6 AdamanzaneH + Glycolate. The space group is P and the cell dimensions are a = (18) Å, b = (3) Å, c = (3) Å. 6

7 CIF File - AdzH+Na-.txt data_'adzh+glycolate' _audit_creation_method SHELXL-97 _chemical_name_systematic 'H^+-1,5,9,13-Tetraazatricyclo[ ^5,^13]docosane _chemical_name_common '3^6AdamanzaneH^+ Glycolate' _chemical_melting_point? _chemical_formula_moiety? _chemical_formula_sum 'C20 H30 N4 O8' _chemical_formula_weight loop atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 'International Tables Vol C Tables and ' 'H' 'H' 'International Tables Vol C Tables and ' 'N' 'N' 'International Tables Vol C Tables and ' 'O' 'O' 'International Tables Vol C Tables and ' _symmetry_cell_setting? _symmetry_space_group_name_h-m? loop symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a (18) _cell_length_b (3) _cell_length_c (3) _cell_angle_alpha _cell_angle_beta _cell_angle_gamma _cell_volume (7) _cell_formula_units_z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used? _cell_measurement_theta_min? _cell_measurement_theta_max? _exptl_crystal_description? _exptl_crystal_colour? _exptl_crystal_size_max? _exptl_crystal_size_mid? _exptl_crystal_size_min? _exptl_crystal_density_meas? 7

8 _exptl_crystal_density_diffrn _exptl_crystal_density_method 'not measured' _exptl_crystal_f_ _exptl_absorpt_coefficient_mu _exptl_absorpt_correction_type? _exptl_absorpt_correction_t_min? _exptl_absorpt_correction_t_max? _exptl_absorpt_process_details? _exptl_special_details ;? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type? _diffrn_measurement_method? _diffrn_detector_area_resol_mean? _diffrn_standards_number? _diffrn_standards_interval_count? _diffrn_standards_interval_time? _diffrn_standards_decay_%? _diffrn_reflns_number _diffrn_reflns_av_r_equivalents _diffrn_reflns_av_sigmai/neti _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max _reflns_number_total 4810 _reflns_number_gt 4459 _reflns_threshold_expression >2sigma(I) _computing_data_collection? _computing_cell_refinement? _computing_data_reduction? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics? _computing_publication_material? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wr and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- 8

9 factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(fo^2^)+(0.1000p)^2^ p] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, ' _refine_ls_abs_structure_flack 2(3) _refine_ls_number_reflns 4810 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_r_factor_all _refine_ls_r_factor_gt _refine_ls_wr_factor_ref _refine_ls_wr_factor_gt _refine_ls_goodness_of_fit_ref _refine_ls_restrained_s_all _refine_ls_shift/su_max _refine_ls_shift/su_mean loop 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 _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N (4) (2) (19) (7) Uani 1 1 d... C2 C (6) (4) (3) (10) Uani 1 1 d... H2A H Uiso 1 1 calc R.. H2B H Uiso 1 1 calc R.. C3 C (6) (3) (3) (10) Uani 1 1 d... H3A H Uiso 1 1 calc R.. H3B H Uiso 1 1 calc R.. C4 C (5) (3) (3) (9) Uani 1 1 d... H4A H Uiso 1 1 calc R.. H4B H Uiso 1 1 calc R.. N5 N (3) (2) (2) (7) Uani 1 1 d... C6 C (4) (3) (2) (8) Uani 1 1 d... H6A H Uiso 1 1 calc R.. H6B H Uiso 1 1 calc R.. 9

10 C7 C (4) (3) (3) (8) Uani 1 1 d... H7A H Uiso 1 1 calc R.. H7B H Uiso 1 1 calc R.. C8 C (5) (4) (3) (9) Uani 1 1 d... H8A H Uiso 1 1 calc R.. H8B H Uiso 1 1 calc R.. N9 N (4) (2) (19) (6) Uani 1 1 d... C10 C (6) (4) (3) (10) Uani 1 1 d... H10A H Uiso 1 1 calc R.. H10B H Uiso 1 1 calc R.. C11 C (6) (4) (3) (12) Uani 1 1 d... H11A H Uiso 1 1 calc R.. H11B H Uiso 1 1 calc R.. C12 C (7) (4) (4) (12) Uani 1 1 d... H12A H Uiso 1 1 calc R.. H12B H Uiso 1 1 calc R.. N13 N (4) (3) (2) (7) Uani 1 1 d... C14 C (7) (4) (4) (13) Uani 1 1 d... H14A H Uiso 1 1 calc R.. H14B H Uiso 1 1 calc R.. C15 C (5) (3) (3) (10) Uani 1 1 d... H15A H Uiso 1 1 calc R.. H15B H Uiso 1 1 calc R.. C16 C (6) (4) (3) (11) Uani 1 1 d... H16A H Uiso 1 1 calc R.. H16B H Uiso 1 1 calc R.. C17 C (6) (3) (3) (10) Uani 1 1 d... H17A H Uiso 1 1 calc R.. H17B H Uiso 1 1 calc R.. C18 C (5) (3) (3) (9) Uani 1 1 d... H18A H Uiso 1 1 calc R.. H18B H Uiso 1 1 calc R.. C19 C (6) (3) (3) (10) Uani 1 1 d... H19A H Uiso 1 1 calc R.. H19B H Uiso 1 1 calc R.. C20 C (6) (3) (3) (11) Uani 1 1 d... H20A H Uiso 1 1 calc R.. H20B H Uiso 1 1 calc R.. C21 C (6) (3) (3) (11) Uani 1 1 d... H21A H Uiso 1 1 calc R.. H21B H Uiso 1 1 calc R.. C22 C (6) (4) (4) (12) Uani 1 1 d... H22A H Uiso 1 1 calc R.. H22B H Uiso 1 1 calc R.. O23 O (4) (2) (18) (7) Uani 1 1 d... O24 O (3) (2) (2) (7) Uani 1 1 d... C25 C (4) (3) (2) (7) Uani 1 1 d... C26 C (5) (4) (3) (10) Uani 1 1 d... H26A H Uiso 1 1 calc R.. H26B H Uiso 1 1 calc R.. O27 O (4) (4) (2) (10) Uani 1 1 d... H27 H (6) 0.226(4) 0.295(3) 0.025(13) Uiso 1 1 d... loop atom_site_aniso_label _atom_site_aniso_u_11 _atom_site_aniso_u_22 10

11 _atom_site_aniso_u_33 _atom_site_aniso_u_23 _atom_site_aniso_u_13 _atom_site_aniso_u_12 N (16) (14) (13) (11) (12) (12) C (2) 0.033(2) 0.029(2) (17) (18) (19) C (2) 0.038(2) (19) (16) (17) (19) C (2) 0.029(2) 0.030(2) (16) (17) (16) N (14) (14) (15) (11) (12) (11) C (17) (19) (18) (14) (14) (15) C (17) 0.032(2) (19) (15) (15) (15) C (2) 0.037(2) (18) (16) (16) (18) N (15) (13) (13) (11) (11) (11) C (2) 0.041(2) 0.034(2) (19) (19) 0.012(2) C (2) 0.070(3) 0.022(2) 0.005(2) (16) (2) C (3) 0.046(3) 0.049(3) (2) (2) (2) N (15) (17) (16) (13) (13) (13) C (3) 0.037(3) 0.056(3) (2) 0.011(3) (2) C (2) (18) 0.036(2) (16) (19) (17) C (3) 0.037(2) (19) (17) 0.006(2) (2) C (3) 0.025(2) 0.036(2) (17) (19) (18) C (3) (16) (18) (13) (18) (16) C (3) 0.030(2) 0.033(2) (17) (19) (19) C (3) 0.022(2) 0.028(2) (15) 0.012(2) (2) C (2) (17) 0.056(3) (17) 0.016(2) (16) C (3) 0.045(3) 0.048(3) (2) 0.004(2) 0.001(2) O (16) (15) (13) (11) (12) (13) O (15) (17) (15) (13) (12) (13) C (18) (16) (17) (13) (14) (13) C (2) 0.046(3) (18) (17) (17) (19) O (2) 0.078(3) (15) (16) (14) 0.019(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C (5).? N1 C (5).? N1 C (6).? C2 C (7).? C3 C (6).? C4 N (5).? N5 C (5).? N5 C (5).? C6 C (6).? 11

12 C7 C (6).? C8 N (5).? N9 C (6).? N9 C (6).? C10 C (7).? C11 C (8).? C12 N (7).? N13 C (7).? N13 C (6).? C14 C (7).? C15 C (7).? C17 C (6).? C18 C (6).? C20 C (7).? C21 C (8).? O23 C (5).? O24 C (5).? C25 C (6).? C26 O (5).? loop geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N1 C (4)..? C16 N1 C (4)..? C17 N1 C (3)..? N1 C2 C (4)..? C2 C3 C (4)..? N5 C4 C (4)..? C6 N5 C (3)..? C6 N5 C (3)..? C20 N5 C (3)..? N5 C6 C (3)..? C6 C7 C (3)..? N9 C8 C (3)..? C19 N9 C (3)..? C19 N9 C (3)..? C10 N9 C (3)..? N9 C10 C (4)..? C12 C11 C (4)..? C11 C12 N (4)..? C14 N13 C (4)..? C14 N13 C (4)..? C22 N13 C (4)..? N13 C14 C (4)..? C14 C15 C (4)..? N1 C16 C (4)..? N1 C17 C (4)..? C17 C18 C (3)..? N9 C19 C (4)..? N5 C20 C (4)..? C20 C21 C (4)..? 12

13 N13 C22 C (4)..? O23 C25 O (4)..? O23 C25 C (3)..? O24 C25 C (4)..? O27 C26 C (4)..? _diffrn_measured_fraction_theta_max _diffrn_reflns_theta_full _diffrn_measured_fraction_theta_full _refine_diff_density_max _refine_diff_density_min _refine_diff_density_rms

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