# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 186/1925 data_rLi.pmdeta _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H39 Li N4' _chemical_formula_weight 390.53 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.0295(2) _cell_length_b 12.6622(4) _cell_length_c 10.5340(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.161(2) _cell_angle_gamma 90.00 _cell_volume 1197.43(6) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.083 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 CCD _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 2943 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0468 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 27.89 _reflns_number_total 2943 _reflns_number_gt 2470 _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^)+(0.0693P)^2^+1.5131P] 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, 876-881' _refine_ls_abs_structure_Flack 0(5) _refine_ls_number_reflns 2943 _refine_ls_number_parameters 267 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0964 _refine_ls_R_factor_gt 0.0776 _refine_ls_wR_factor_ref 0.1877 _refine_ls_wR_factor_gt 0.1734 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.019 _refine_ls_shift/su_mean 0.001 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 -0.7465(3) 0.1921 0.1569(3) 0.0175(7) Uani 1 1 d . . . N2 N -0.4131(4) 0.3479(4) 0.2296(4) 0.0284(9) Uani 1 1 d . . . N3 N -0.4133(4) 0.0636(4) 0.2438(4) 0.0275(9) Uani 1 1 d . . . N4 N -0.4556(3) 0.2172(4) 0.4488(3) 0.0221(7) Uani 1 1 d . . . C1 C -0.6444(4) 0.1960(5) -0.0467(4) 0.0279(9) Uani 1 1 d . . . H1A H -0.6474 0.2734 -0.0488 0.042 Uiso 1 1 calc R . . H1B H -0.6578 0.1686 -0.1342 0.042 Uiso 1 1 calc R . . H1C H -0.5479 0.1726 -0.0046 0.042 Uiso 1 1 calc R . . C2 C -0.7684(4) 0.1548(4) 0.0267(4) 0.0193(8) Uani 1 1 d . . . H2 H -0.7635 0.0759 0.0278 0.023 Uiso 1 1 calc R . . C3 C -0.9196(4) 0.1882(4) -0.0445(3) 0.0201(8) Uani 1 1 d . . . C4 C -0.9571(5) 0.2947(5) -0.0543(4) 0.0296(10) Uani 1 1 d . . . H4 H -0.8891 0.3463 -0.0175 0.036 Uiso 1 1 calc R . . C5 C -1.0930(6) 0.3266(6) -0.1171(4) 0.0403(13) Uani 1 1 d . . . H5 H -1.1160 0.3996 -0.1251 0.048 Uiso 1 1 calc R . . C6 C -1.1949(5) 0.2522(6) -0.1682(4) 0.0373(13) Uani 1 1 d . . . H6 H -1.2888 0.2738 -0.2091 0.045 Uiso 1 1 calc R . . C7 C -1.1590(5) 0.1467(6) -0.1591(4) 0.0387(13) Uani 1 1 d . . . H7 H -1.2283 0.0954 -0.1946 0.046 Uiso 1 1 calc R . . C8 C -1.0211(5) 0.1143(5) -0.0980(4) 0.0270(9) Uani 1 1 d . . . H8 H -0.9969 0.0412 -0.0932 0.032 Uiso 1 1 calc R . . C9 C -0.8608(5) 0.1501(4) 0.2296(4) 0.0240(9) Uani 1 1 d . . . H9A H -0.8297 0.0793 0.2625 0.029 Uiso 1 1 calc R . . H9B H -0.9542 0.1415 0.1723 0.029 Uiso 1 1 calc R . . C10 C -0.8904(4) 0.2200(4) 0.3407(4) 0.0211(9) Uani 1 1 d . . . C11 C -0.8907(4) 0.3295(5) 0.3288(4) 0.0254(9) Uani 1 1 d . . . H11 H -0.8683 0.3602 0.2508 0.030 Uiso 1 1 calc R . . C12 C -0.9229(5) 0.3951(5) 0.4280(5) 0.0353(12) Uani 1 1 d . . . H12 H -0.9219 0.4696 0.4175 0.042 Uiso 1 1 calc R . . C13 C -0.9565(5) 0.3517(6) 0.5421(5) 0.0413(14) Uani 1 1 d . . . H13 H -0.9787 0.3961 0.6102 0.050 Uiso 1 1 calc R . . C14 C -0.9574(5) 0.2438(6) 0.5557(4) 0.0408(14) Uani 1 1 d . . . H14 H -0.9796 0.2138 0.6341 0.049 Uiso 1 1 calc R . . C15 C -0.9262(5) 0.1779(5) 0.4558(4) 0.0302(11) Uani 1 1 d . . . H15 H -0.9294 0.1035 0.4664 0.036 Uiso 1 1 calc R . . C16 C -0.2716(6) 0.0601(6) 0.1969(7) 0.0549(16) Uani 1 1 d . . . H16A H -0.2311 -0.0116 0.2065 0.082 Uiso 1 1 calc R . . H16B H -0.2039 0.1096 0.2453 0.082 Uiso 1 1 calc R . . H16C H -0.2821 0.0798 0.1064 0.082 Uiso 1 1 calc R . . C17 C -0.5105(6) -0.0178(5) 0.1890(7) 0.0477(15) Uani 1 1 d . . . H17A H -0.5217 -0.0110 0.0958 0.071 Uiso 1 1 calc R . . H17B H -0.6081 -0.0109 0.2207 0.071 Uiso 1 1 calc R . . H17C H -0.4679 -0.0870 0.2130 0.071 Uiso 1 1 calc R . . C18 C -0.4017(6) 0.0389(5) 0.3857(5) 0.0386(12) Uani 1 1 d . . . H18A H -0.5008 0.0177 0.4090 0.046 Uiso 1 1 calc R . . H18B H -0.3326 -0.0211 0.4046 0.046 Uiso 1 1 calc R . . C19 C -0.3485(5) 0.1295(5) 0.4618(4) 0.0325(11) Uani 1 1 d . . . H19A H -0.2524 0.1535 0.4345 0.039 Uiso 1 1 calc R . . H19B H -0.3308 0.1085 0.5526 0.039 Uiso 1 1 calc R . . C20 C -0.5589(5) 0.2098(5) 0.5463(4) 0.0332(11) Uani 1 1 d . . . H20A H -0.6158 0.1440 0.5348 0.050 Uiso 1 1 calc R . . H20B H -0.6274 0.2701 0.5382 0.050 Uiso 1 1 calc R . . H20C H -0.5026 0.2105 0.6312 0.050 Uiso 1 1 calc R . . C21 C -0.3839(6) 0.3222(5) 0.4623(5) 0.0420(13) Uani 1 1 d . . . H21A H -0.3093 0.3214 0.5384 0.050 Uiso 1 1 calc R . . H21B H -0.4605 0.3754 0.4774 0.050 Uiso 1 1 calc R . . C22 C -0.3090(6) 0.3553(5) 0.3492(5) 0.0401(12) Uani 1 1 d . . . H22A H -0.2732 0.4289 0.3610 0.048 Uiso 1 1 calc R . . H22B H -0.2215 0.3094 0.3417 0.048 Uiso 1 1 calc R . . C23 C -0.5243(7) 0.4301(5) 0.2096(7) 0.0501(16) Uani 1 1 d . . . H23A H -0.4751 0.4991 0.2109 0.075 Uiso 1 1 calc R . . H23B H -0.5902 0.4272 0.2776 0.075 Uiso 1 1 calc R . . H23C H -0.5829 0.4197 0.1267 0.075 Uiso 1 1 calc R . . C24 C -0.3157(6) 0.3530(5) 0.1260(6) 0.0423(13) Uani 1 1 d . . . H24A H -0.3741 0.3372 0.0444 0.063 Uiso 1 1 calc R . . H24B H -0.2353 0.3011 0.1421 0.063 Uiso 1 1 calc R . . H24C H -0.2730 0.4239 0.1228 0.063 Uiso 1 1 calc R . . Li1 Li -0.5445(7) 0.2083(6) 0.2431(6) 0.0190(13) Uani 1 1 d . . . 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 N1 0.0162(14) 0.0219(17) 0.0147(14) 0.0009(13) 0.0037(12) -0.0025(13) N2 0.036(2) 0.0243(19) 0.0247(18) 0.0071(15) 0.0008(16) -0.0124(17) N3 0.0230(18) 0.026(2) 0.031(2) -0.0051(16) -0.0094(15) 0.0068(16) N4 0.0150(15) 0.031(2) 0.0199(16) 0.0023(15) -0.0008(13) -0.0030(14) C1 0.0234(19) 0.038(3) 0.024(2) -0.003(2) 0.0071(17) 0.002(2) C2 0.0172(17) 0.0186(19) 0.0215(19) -0.0017(16) -0.0009(15) 0.0001(15) C3 0.0185(18) 0.030(2) 0.0119(16) -0.0006(16) 0.0022(14) 0.0006(17) C4 0.035(2) 0.027(2) 0.027(2) -0.0048(18) 0.002(2) 0.0084(19) C5 0.040(3) 0.057(4) 0.024(2) 0.001(2) 0.004(2) 0.027(3) C6 0.022(2) 0.069(4) 0.020(2) 0.003(2) -0.0027(18) 0.015(2) C7 0.025(2) 0.071(4) 0.019(2) 0.000(2) -0.0028(18) -0.015(3) C8 0.026(2) 0.035(2) 0.0194(19) 0.0017(18) 0.0020(17) -0.0044(19) C9 0.0216(19) 0.024(2) 0.026(2) -0.0045(18) 0.0022(16) -0.0069(17) C10 0.0101(16) 0.032(2) 0.0206(18) -0.0022(17) 0.0002(14) -0.0021(16) C11 0.0168(18) 0.033(3) 0.026(2) -0.0070(18) 0.0033(17) -0.0022(17) C12 0.024(2) 0.038(3) 0.044(3) -0.016(2) 0.005(2) -0.001(2) C13 0.021(2) 0.067(4) 0.038(3) -0.025(3) 0.011(2) -0.010(2) C14 0.026(2) 0.077(4) 0.022(2) -0.006(2) 0.0084(19) -0.013(2) C15 0.022(2) 0.046(3) 0.023(2) 0.0002(19) 0.0045(17) -0.0094(19) C16 0.041(3) 0.056(4) 0.072(4) 0.001(3) 0.023(3) 0.013(3) C17 0.038(3) 0.020(2) 0.084(5) 0.001(3) 0.001(3) 0.005(2) C18 0.035(3) 0.035(3) 0.046(3) 0.012(2) 0.002(2) 0.002(2) C19 0.023(2) 0.052(3) 0.021(2) 0.007(2) -0.0017(17) 0.011(2) C20 0.030(2) 0.050(3) 0.0202(19) 0.000(2) 0.0045(17) 0.003(2) C21 0.044(3) 0.044(3) 0.035(3) 0.000(2) -0.011(2) -0.020(2) C22 0.038(3) 0.040(3) 0.041(3) 0.002(2) -0.003(2) -0.010(2) C23 0.044(3) 0.028(3) 0.083(5) -0.002(3) 0.025(3) -0.005(2) C24 0.030(2) 0.040(3) 0.058(3) 0.020(3) 0.010(2) -0.003(2) Li1 0.018(3) 0.019(3) 0.019(3) -0.004(3) -0.003(2) 0.003(3) _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 C2 1.444(5) . ? N1 C9 1.450(5) . ? N1 Li1 1.959(7) . ? N2 C23 1.445(7) . ? N2 C24 1.474(7) . ? N2 C22 1.491(6) . ? N2 Li1 2.143(8) . ? N3 C16 1.421(7) . ? N3 C17 1.434(7) . ? N3 C18 1.520(7) . ? N3 Li1 2.181(8) . ? N4 C20 1.462(5) . ? N4 C19 1.469(6) . ? N4 C21 1.478(6) . ? N4 Li1 2.231(7) . ? C1 C2 1.521(5) . ? C2 C3 1.544(5) . ? C3 C8 1.386(6) . ? C3 C4 1.392(6) . ? C4 C5 1.390(6) . ? C5 C6 1.384(8) . ? C6 C7 1.376(8) . ? C7 C8 1.401(7) . ? C9 C10 1.514(6) . ? C10 C11 1.393(7) . ? C10 C15 1.393(6) . ? C11 C12 1.390(6) . ? C12 C13 1.384(8) . ? C13 C14 1.374(9) . ? C14 C15 1.396(7) . ? C18 C19 1.452(8) . ? C21 C22 1.493(8) . ? 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 C2 N1 C9 110.4(3) . . ? C2 N1 Li1 120.0(3) . . ? C9 N1 Li1 118.3(3) . . ? C23 N2 C24 108.7(4) . . ? C23 N2 C22 116.3(5) . . ? C24 N2 C22 104.5(4) . . ? C23 N2 Li1 102.9(3) . . ? C24 N2 Li1 117.6(4) . . ? C22 N2 Li1 107.4(3) . . ? C16 N3 C17 111.8(5) . . ? C16 N3 C18 111.5(4) . . ? C17 N3 C18 102.9(4) . . ? C16 N3 Li1 122.3(4) . . ? C17 N3 Li1 107.1(3) . . ? C18 N3 Li1 99.0(3) . . ? C20 N4 C19 110.4(4) . . ? C20 N4 C21 107.2(4) . . ? C19 N4 C21 113.2(4) . . ? C20 N4 Li1 119.2(3) . . ? C19 N4 Li1 102.5(3) . . ? C21 N4 Li1 104.3(3) . . ? N1 C2 C1 109.7(3) . . ? N1 C2 C3 113.3(3) . . ? C1 C2 C3 108.7(3) . . ? C8 C3 C4 118.6(4) . . ? C8 C3 C2 121.6(4) . . ? C4 C3 C2 119.8(4) . . ? C5 C4 C3 120.8(5) . . ? C6 C5 C4 120.2(5) . . ? C7 C6 C5 119.5(4) . . ? C6 C7 C8 120.5(5) . . ? C3 C8 C7 120.3(5) . . ? N1 C9 C10 112.9(3) . . ? C11 C10 C15 117.5(4) . . ? C11 C10 C9 120.7(4) . . ? C15 C10 C9 121.7(4) . . ? C12 C11 C10 121.7(4) . . ? C13 C12 C11 119.9(5) . . ? C14 C13 C12 119.3(5) . . ? C13 C14 C15 120.8(5) . . ? C10 C15 C14 120.8(5) . . ? C19 C18 N3 111.4(4) . . ? C18 C19 N4 111.7(4) . . ? N4 C21 C22 114.0(4) . . ? N2 C22 C21 111.0(4) . . ? N1 Li1 N2 123.4(4) . . ? N1 Li1 N3 113.1(3) . . ? N2 Li1 N3 112.9(3) . . ? N1 Li1 N4 132.5(3) . . ? N2 Li1 N4 83.0(3) . . ? N3 Li1 N4 84.3(3) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.860 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.063 data_rLi.thf _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H24 Li N O' _chemical_formula_weight 289.33 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' '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' 'Li' 'Li' -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M P4(3)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+1/2, x+1/2, z+3/4' '-x, -y, z+1/2' 'y+1/2, -x+1/2, z+1/4' 'x+1/2, -y+1/2, -z+1/4' '-x+1/2, y+1/2, -z+3/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 11.5270(10) _cell_length_b 11.5270(10) _cell_length_c 25.4810(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3385.7(4) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.135 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 35455 _diffrn_reflns_av_R_equivalents 0.0865 _diffrn_reflns_av_sigmaI/netI 0.0647 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 27.89 _reflns_number_total 4039 _reflns_number_gt 3102 _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^)+(0.0430P)^2^+1.4777P] 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, 876-881' _refine_ls_abs_structure_Flack 0.4(21) _refine_ls_number_reflns 4039 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0981 _refine_ls_R_factor_gt 0.0682 _refine_ls_wR_factor_ref 0.1270 _refine_ls_wR_factor_gt 0.1178 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.001 _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 0.13037(15) 1.02811(14) 0.88366(6) 0.0341(4) Uani 1 1 d . B . N1 N 0.16377(15) 0.97930(15) 1.01940(7) 0.0228(4) Uani 1 1 d . . . C1 C 0.16912(18) 0.85298(18) 1.02247(8) 0.0224(5) Uani 1 1 d . . . H1 H 0.2374 0.8264 1.0015 0.027 Uiso 1 1 calc R . . Li1 Li 0.0884(3) 1.0444(3) 0.95557(13) 0.0273(8) Uani 1 1 d . . . C2 C 0.0597(2) 0.8012(2) 0.99779(9) 0.0326(5) Uani 1 1 d . . . H2A H -0.0088 0.8293 1.0167 0.049 Uiso 1 1 calc R . . H2B H 0.0630 0.7164 1.0000 0.049 Uiso 1 1 calc R . . H2C H 0.0547 0.8248 0.9609 0.049 Uiso 1 1 calc R . . C3 C 0.18256(18) 0.80583(18) 1.07855(8) 0.0219(5) Uani 1 1 d . . . C4 C 0.2684(2) 0.7269(2) 1.09175(9) 0.0279(5) Uani 1 1 d . . . H4 H 0.3231 0.7041 1.0659 0.033 Uiso 1 1 calc R . . C5 C 0.2764(2) 0.6802(2) 1.14190(9) 0.0341(6) Uani 1 1 d . . . H5 H 0.3358 0.6257 1.1497 0.041 Uiso 1 1 calc R . . C6 C 0.1991(2) 0.7123(2) 1.18022(9) 0.0332(6) Uani 1 1 d . . . H6 H 0.2039 0.6795 1.2144 0.040 Uiso 1 1 calc R . . C7 C 0.1141(2) 0.7928(2) 1.16857(9) 0.0336(6) Uani 1 1 d . . . H7 H 0.0609 0.8165 1.1949 0.040 Uiso 1 1 calc R . . C8 C 0.1063(2) 0.8391(2) 1.11833(9) 0.0303(5) Uani 1 1 d . . . H8 H 0.0477 0.8947 1.1109 0.036 Uiso 1 1 calc R . . C9 C 0.27628(18) 1.03035(19) 1.03328(8) 0.0230(5) Uani 1 1 d . . . H9A H 0.3053 0.9925 1.0656 0.028 Uiso 1 1 calc R . . H9B H 0.2650 1.1137 1.0412 0.028 Uiso 1 1 calc R . . C10 C 0.36728(18) 1.01864(18) 0.99067(8) 0.0221(5) Uani 1 1 d . . . C11 C 0.3717(2) 1.0976(2) 0.94935(9) 0.0276(5) Uani 1 1 d . . . H11 H 0.3191 1.1610 0.9490 0.033 Uiso 1 1 calc R . . C12 C 0.4506(2) 1.0864(2) 0.90878(10) 0.0359(6) Uani 1 1 d . . . H12 H 0.4523 1.1422 0.8814 0.043 Uiso 1 1 calc R . . C13 C 0.5268(2) 0.9939(2) 0.90817(10) 0.0380(6) Uani 1 1 d . . . H13 H 0.5804 0.9850 0.8801 0.046 Uiso 1 1 calc R . . C14 C 0.5243(2) 0.9144(2) 0.94875(10) 0.0374(6) Uani 1 1 d . . . H14 H 0.5761 0.8504 0.9485 0.045 Uiso 1 1 calc R . . C15 C 0.44642(18) 0.9277(2) 0.99003(9) 0.0290(5) Uani 1 1 d . . . H15 H 0.4473 0.8737 1.0182 0.035 Uiso 1 1 calc R . . C16 C 0.1350(3) 1.1251(2) 0.84781(9) 0.0440(7) Uani 1 1 d . B . H16A H 0.2036 1.1744 0.8550 0.053 Uiso 1 1 calc R . . H16B H 0.0641 1.1732 0.8506 0.053 Uiso 1 1 calc R . . C17 C 0.1436(3) 1.0706(3) 0.79497(11) 0.0653(10) Uani 1 1 d . . . H17A H 0.2133 1.0993 0.7763 0.078 Uiso 1 1 calc R A 1 H17B H 0.0743 1.0897 0.7737 0.078 Uiso 1 1 calc R A 1 C18A C 0.1522(10) 0.9334(10) 0.8037(4) 0.055(3) Uani 0.30 1 d P B 1 H18A H 0.0763 0.8948 0.7989 0.066 Uiso 0.30 1 calc PR B 1 H18B H 0.2104 0.8974 0.7802 0.066 Uiso 0.30 1 calc PR B 1 C18B C 0.2290(5) 0.9735(5) 0.80787(18) 0.0590(13) Uani 0.70 1 d P B 2 H18C H 0.2251 0.9109 0.7813 0.071 Uiso 0.70 1 calc PR B 2 H18D H 0.3095 1.0035 0.8095 0.071 Uiso 0.70 1 calc PR B 2 C19 C 0.1906(2) 0.9310(2) 0.86010(10) 0.0427(7) Uani 1 1 d . . . H19A H 0.1681 0.8572 0.8771 0.051 Uiso 1 1 calc R B 1 H19B H 0.2757 0.9408 0.8629 0.051 Uiso 1 1 calc R B 1 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 0.0487(11) 0.0310(9) 0.0225(8) 0.0030(7) 0.0032(8) 0.0137(8) N1 0.0188(9) 0.0255(10) 0.0240(9) 0.0069(8) 0.0002(7) 0.0011(7) C1 0.0201(11) 0.0265(12) 0.0206(10) 0.0041(9) 0.0001(9) 0.0002(9) Li1 0.035(2) 0.029(2) 0.0184(17) 0.0015(16) -0.0016(16) 0.0039(16) C2 0.0342(13) 0.0366(14) 0.0268(11) 0.0076(11) -0.0075(11) -0.0062(10) C3 0.0223(11) 0.0197(11) 0.0236(10) 0.0038(8) -0.0009(9) -0.0051(9) C4 0.0268(12) 0.0283(13) 0.0285(12) 0.0029(10) -0.0044(10) 0.0016(9) C5 0.0337(13) 0.0330(14) 0.0355(13) 0.0107(11) -0.0116(11) -0.0002(11) C6 0.0424(15) 0.0321(13) 0.0250(11) 0.0120(11) -0.0095(11) -0.0151(11) C7 0.0372(14) 0.0378(14) 0.0259(12) 0.0048(11) 0.0058(11) -0.0092(11) C8 0.0272(12) 0.0307(13) 0.0331(13) 0.0104(10) 0.0015(10) 0.0011(10) C9 0.0258(12) 0.0218(11) 0.0213(10) 0.0022(9) -0.0006(9) 0.0008(9) C10 0.0199(11) 0.0245(11) 0.0220(11) -0.0028(9) -0.0042(9) -0.0035(9) C11 0.0261(12) 0.0260(12) 0.0306(12) 0.0017(10) 0.0002(10) -0.0047(9) C12 0.0311(14) 0.0447(15) 0.0320(13) 0.0021(11) 0.0031(11) -0.0139(11) C13 0.0257(13) 0.0538(17) 0.0344(13) -0.0122(12) 0.0104(11) -0.0123(12) C14 0.0214(12) 0.0406(15) 0.0501(16) -0.0157(13) 0.0000(11) 0.0039(11) C15 0.0238(12) 0.0282(12) 0.0350(13) 0.0003(10) -0.0031(10) 0.0002(9) C16 0.0628(19) 0.0358(15) 0.0335(13) 0.0097(12) -0.0037(13) -0.0008(13) C17 0.092(3) 0.072(2) 0.0316(15) 0.0095(15) 0.0113(16) 0.003(2) C18A 0.051(7) 0.057(7) 0.057(7) -0.020(5) -0.003(5) 0.002(6) C18B 0.068(3) 0.061(3) 0.048(3) -0.018(2) 0.023(3) 0.003(3) C19 0.0493(17) 0.0339(14) 0.0450(15) -0.0077(12) 0.0134(13) 0.0090(13) _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 C16 1.445(3) . ? O1 C19 1.447(3) . ? O1 Li1 1.905(4) . ? N1 C1 1.460(3) . ? N1 C9 1.467(3) . ? N1 Li1 1.970(4) 7_467 ? N1 Li1 1.991(4) . ? C1 C2 1.531(3) . ? C1 C3 1.537(3) . ? Li1 N1 1.970(4) 7_467 ? Li1 Li1 2.375(7) 7_467 ? Li1 C9 2.769(4) 7_467 ? C3 C4 1.385(3) . ? C3 C8 1.396(3) . ? C4 C5 1.390(3) . ? C5 C6 1.373(3) . ? C6 C7 1.381(4) . ? C7 C8 1.390(3) . ? C9 C10 1.516(3) . ? C9 Li1 2.769(4) 7_467 ? C10 C15 1.390(3) . ? C10 C11 1.393(3) . ? C11 C12 1.382(3) . ? C12 C13 1.382(4) . ? C13 C14 1.381(4) . ? C14 C15 1.391(3) . ? C16 C17 1.489(4) . ? C17 C18B 1.526(6) . ? C17 C18A 1.601(11) . ? C18A C19 1.503(11) . ? C18B C19 1.486(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 O1 C19 108.56(19) . . ? C16 O1 Li1 122.76(18) . . ? C19 O1 Li1 126.69(18) . . ? C1 N1 C9 110.47(17) . . ? C1 N1 Li1 130.47(18) . 7_467 ? C9 N1 Li1 106.45(17) . 7_467 ? C1 N1 Li1 116.01(17) . . ? C9 N1 Li1 115.55(17) . . ? Li1 N1 Li1 73.68(17) 7_467 . ? N1 C1 C2 109.39(17) . . ? N1 C1 C3 114.02(17) . . ? C2 C1 C3 109.10(17) . . ? O1 Li1 N1 122.87(19) . 7_467 ? O1 Li1 N1 129.6(2) . . ? N1 Li1 N1 106.11(17) 7_467 . ? O1 Li1 Li1 173.02(17) . 7_467 ? N1 Li1 Li1 53.57(15) 7_467 7_467 ? N1 Li1 Li1 52.75(14) . 7_467 ? O1 Li1 C9 104.80(16) . 7_467 ? N1 Li1 C9 30.54(9) 7_467 7_467 ? N1 Li1 C9 112.68(16) . 7_467 ? Li1 Li1 C9 69.20(15) 7_467 7_467 ? C4 C3 C8 117.0(2) . . ? C4 C3 C1 122.01(19) . . ? C8 C3 C1 120.97(19) . . ? C3 C4 C5 121.7(2) . . ? C6 C5 C4 120.4(2) . . ? C5 C6 C7 119.3(2) . . ? C6 C7 C8 120.1(2) . . ? C7 C8 C3 121.5(2) . . ? N1 C9 C10 113.78(17) . . ? N1 C9 Li1 43.01(12) . 7_467 ? C10 C9 Li1 139.71(16) . 7_467 ? C15 C10 C11 117.4(2) . . ? C15 C10 C9 121.99(19) . . ? C11 C10 C9 120.6(2) . . ? C12 C11 C10 121.9(2) . . ? C11 C12 C13 119.9(2) . . ? C14 C13 C12 119.3(2) . . ? C13 C14 C15 120.5(2) . . ? C10 C15 C14 121.0(2) . . ? O1 C16 C17 104.3(2) . . ? C16 C17 C18B 99.1(3) . . ? C16 C17 C18A 107.2(4) . . ? C18B C17 C18A 37.4(4) . . ? C19 C18A C17 99.7(6) . . ? C19 C18B C17 104.0(3) . . ? O1 C19 C18B 105.1(3) . . ? O1 C19 C18A 104.0(4) . . ? C18B C19 C18A 39.3(4) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.237 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.040