# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Xiang Zhao' _publ_contact_author_email xzhao001@student.ucr.edu loop_ _publ_author_name 'Pingyun Feng' 'Xiang Zhao' 'Tao Wu' 'Shou-Tian Zheng' 'Le Wang' 'Xianhui Bu' data_Li-Cubane-1 _database_code_depnum_ccdc_archive 'CCDC 778254' #TrackingRef 'Li-Cubane.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic tetrakis(m3-4-hydroxypyridine)-tetra-lithium _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H16 Li4 N4 O5' _chemical_formula_weight 105.03 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P-42c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' '-x, y, -z+1/2' 'x, -y, -z+1/2' '-y, -x, z+1/2' 'y, x, z+1/2' _cell_length_a 10.9909(10) _cell_length_b 10.9909(10) _cell_length_c 10.991 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1327.70(17) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.051 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _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 2848 _diffrn_reflns_av_R_equivalents 0.0628 _diffrn_reflns_av_sigmaI/netI 0.0619 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 19.82 _reflns_number_total 611 _reflns_number_gt 536 _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- 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^)+(0.0000P)^2^+7.2470P] 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 SHELXL _refine_ls_extinction_coef 0.018(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(8) _refine_ls_number_reflns 611 _refine_ls_number_parameters 76 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1059 _refine_ls_R_factor_gt 0.0942 _refine_ls_wR_factor_ref 0.1908 _refine_ls_wR_factor_gt 0.1859 _refine_ls_goodness_of_fit_ref 1.176 _refine_ls_restrained_S_all 1.176 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 O1 O 0.9037(6) 0.4106(6) 0.1586(5) 0.030(2) Uani 1 1 d . . . N1 N 0.7012(7) 0.1808(8) -0.0616(7) 0.037(3) Uani 1 1 d . . . C2 C 0.7845(13) 0.3766(10) -0.0150(11) 0.085(5) Uani 1 1 d . . . H2 H 0.7934 0.4568 -0.0403 0.103 Uiso 1 1 calc R . . C5 C 0.8271(12) 0.2167(9) 0.1082(10) 0.070(5) Uani 1 1 d . . . H5 H 0.8677 0.1813 0.1734 0.084 Uiso 1 1 calc R . . C3 C 0.7178(14) 0.2975(11) -0.0817(13) 0.114(7) Uani 1 1 d . . . H3 H 0.6791 0.3296 -0.1497 0.136 Uiso 1 1 calc R . . C4 C 0.7577(11) 0.1462(9) 0.0341(11) 0.061(4) Uani 1 1 d . . . H4 H 0.7505 0.0645 0.0550 0.073 Uiso 1 1 calc R . . C1 C 0.8379(8) 0.3380(8) 0.0884(8) 0.026(3) Uani 1 1 d . . . Li1 Li 1.0816(14) 0.4108(13) 0.1636(13) 0.028(4) Uani 1 1 d . . . O2 O 0.0000 0.5000 0.7500 0.169(16) Uiso 0.60 4 d SP . . O3 O 0.5000 0.5000 0.7500 0.15(2) Uiso 0.40 4 d SP . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.030(4) 0.024(4) 0.035(4) -0.003(4) -0.007(4) -0.002(4) N1 0.037(5) 0.039(6) 0.034(5) 0.000(5) -0.023(5) 0.002(4) C2 0.154(14) 0.036(8) 0.067(9) 0.012(7) -0.098(10) -0.009(8) C5 0.128(12) 0.024(7) 0.058(8) 0.002(7) -0.067(8) -0.032(7) C3 0.182(17) 0.026(8) 0.133(14) -0.008(8) -0.128(13) -0.024(8) C4 0.103(11) 0.020(7) 0.060(8) -0.001(7) -0.024(9) -0.017(7) C1 0.022(6) 0.022(7) 0.034(6) -0.012(6) -0.005(6) -0.009(5) Li1 0.030(9) 0.022(9) 0.033(8) 0.004(9) 0.013(9) -0.003(9) _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 O1 C1 1.324(9) . ? O1 Li1 1.957(16) . ? O1 Li1 1.960(14) 5_755 ? O1 Li1 1.970(15) 2_765 ? N1 C4 1.279(12) . ? N1 C3 1.315(13) . ? N1 Li1 1.990(15) 4_645 ? C2 C1 1.347(12) . ? C2 C3 1.352(14) . ? C5 C1 1.356(12) . ? C5 C4 1.359(13) . ? Li1 O1 1.960(14) 5_755 ? Li1 O1 1.970(15) 2_765 ? Li1 N1 1.990(15) 3_665 ? Li1 Li1 2.61(3) 5_755 ? Li1 Li1 2.66(3) 2_765 ? Li1 Li1 2.73(3) 6_565 ? 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 C1 O1 Li1 124.2(7) . . ? C1 O1 Li1 128.8(7) . 5_755 ? Li1 O1 Li1 83.6(7) . 5_755 ? C1 O1 Li1 131.4(7) . 2_765 ? Li1 O1 Li1 85.2(7) . 2_765 ? Li1 O1 Li1 87.9(7) 5_755 2_765 ? C4 N1 C3 111.1(9) . . ? C4 N1 Li1 126.9(8) . 4_645 ? C3 N1 Li1 121.7(9) . 4_645 ? C1 C2 C3 119.4(10) . . ? C1 C5 C4 121.0(10) . . ? N1 C3 C2 127.7(12) . . ? N1 C4 C5 126.5(10) . . ? O1 C1 C2 122.7(9) . . ? O1 C1 C5 123.1(9) . . ? C2 C1 C5 113.9(9) . . ? O1 Li1 O1 96.4(7) . 5_755 ? O1 Li1 O1 94.7(7) . 2_765 ? O1 Li1 O1 91.3(7) 5_755 2_765 ? O1 Li1 N1 122.0(9) . 3_665 ? O1 Li1 N1 121.0(8) 5_755 3_665 ? O1 Li1 N1 123.8(8) 2_765 3_665 ? O1 Li1 Li1 48.2(5) . 5_755 ? O1 Li1 Li1 48.1(5) 5_755 5_755 ? O1 Li1 Li1 94.4(5) 2_765 5_755 ? N1 Li1 Li1 141.8(5) 3_665 5_755 ? O1 Li1 Li1 47.6(5) . 2_765 ? O1 Li1 Li1 93.2(5) 5_755 2_765 ? O1 Li1 Li1 47.2(5) 2_765 2_765 ? N1 Li1 Li1 145.7(5) 3_665 2_765 ? Li1 Li1 Li1 62.4(7) 5_755 2_765 ? O1 Li1 Li1 91.2(5) . 6_565 ? O1 Li1 Li1 46.2(5) 5_755 6_565 ? O1 Li1 Li1 45.9(5) 2_765 6_565 ? N1 Li1 Li1 146.8(5) 3_665 6_565 ? Li1 Li1 Li1 59.6(6) 5_755 6_565 ? Li1 Li1 Li1 58.0(6) 2_765 6_565 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 19.82 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.262 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.061