# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Antonio Otero' _publ_contact_author_email ANTONIO.OTERO@UCLM.ES _publ_section_title ; New Achiral and Chiral NNE heteroscorpionate Ligands. Synthesis of Homoleptic Lithium Complexes as well as Halide and Alkyl Scandium and Yttrium Complexes ; loop_ _publ_author_name 'Antonio Otero' 'Carlos Alonso-Moreno' 'Juan Fernandez-Baeza' 'Agustin Lara-Sanch' ; I.L.-S.-Solera ; 'Isabel Marquez-Segovia' 'Emilia Martinez-Caballero' 'Ana M Rodriguez' ; L.F.Sanchez-Barba ; # Attachment '5_6_8.CIF' data_5 _database_code_depnum_ccdc_archive 'CCDC 741155' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H21 N5 S' _chemical_formula_sum 'C18 H21 N5 S' _chemical_formula_weight 339.46 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.048(2) _cell_length_b 11.477(2) _cell_length_c 13.263(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.43(3) _cell_angle_gamma 90.00 _cell_volume 1833.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 437 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 16.74 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.229 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.185 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.923 _exptl_absorpt_correction_T_max 0.951 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9267 _diffrn_reflns_av_R_equivalents 0.1204 _diffrn_reflns_av_sigmaI/netI 0.2540 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3192 _reflns_number_gt 836 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS, XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0993P)^2^+0.0000P] 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_number_reflns 3192 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1916 _refine_ls_R_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.1905 _refine_ls_wR_factor_gt 0.1301 _refine_ls_goodness_of_fit_ref 0.844 _refine_ls_restrained_S_all 0.844 _refine_ls_shift/su_max 0.004 _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 S1 S 0.97213(13) 0.35490(13) 0.88941(9) 0.0950(6) Uani 1 1 d . . . N1 N 0.8163(3) 0.3105(4) 0.6578(2) 0.0638(10) Uani 1 1 d . . . N2 N 0.8058(3) 0.4216(4) 0.6226(3) 0.0732(11) Uani 1 1 d . . . N3 N 1.0165(3) 0.2798(4) 0.5417(3) 0.0779(12) Uani 1 1 d . . . N4 N 0.9914(3) 0.2174(4) 0.6272(3) 0.0732(11) Uani 1 1 d . . . N5 N 1.0283(3) 0.4451(4) 0.7102(3) 0.0688(12) Uani 1 1 d . . . C1 C 0.7062(4) 0.4234(6) 0.5770(3) 0.0793(15) Uani 1 1 d . . . C2 C 0.6573(4) 0.3145(6) 0.5832(4) 0.0871(16) Uani 1 1 d . . . H2 H 0.5875 0.2949 0.5578 0.104 Uiso 1 1 calc R . . C3 C 0.7282(5) 0.2403(5) 0.6326(4) 0.0783(15) Uani 1 1 d . . . C4 C 0.6645(4) 0.5325(5) 0.5290(4) 0.118(2) Uani 1 1 d . . . H4A H 0.7206 0.5917 0.5335 0.177 Uiso 1 1 calc R . . H4B H 0.5990 0.5583 0.5633 0.177 Uiso 1 1 calc R . . H4C H 0.6470 0.5177 0.4595 0.177 Uiso 1 1 calc R . . C5 C 0.7218(4) 0.1146(5) 0.6562(4) 0.115(2) Uani 1 1 d . . . H5A H 0.7855 0.0756 0.6292 0.173 Uiso 1 1 calc R . . H5B H 0.6555 0.0825 0.6267 0.173 Uiso 1 1 calc R . . H5C H 0.7202 0.1042 0.7280 0.173 Uiso 1 1 calc R . . C6 C 1.0427(5) 0.1114(5) 0.6292(5) 0.0859(16) Uani 1 1 d . . . C7 C 1.0984(5) 0.1068(6) 0.5411(6) 0.105(2) Uani 1 1 d . . . H7 H 1.1416 0.0446 0.5195 0.126 Uiso 1 1 calc R . . C8 C 1.0809(5) 0.2091(6) 0.4881(4) 0.0884(17) Uani 1 1 d . . . C9 C 1.0354(5) 0.0316(5) 0.7184(4) 0.123(2) Uani 1 1 d . . . H9A H 1.0681 0.0688 0.7763 0.185 Uiso 1 1 calc R . . H9B H 1.0746 -0.0393 0.7044 0.185 Uiso 1 1 calc R . . H9C H 0.9590 0.0143 0.7317 0.185 Uiso 1 1 calc R . . C10 C 1.1225(4) 0.2450(6) 0.3875(4) 0.125(2) Uani 1 1 d . . . H10A H 1.0743 0.2147 0.3358 0.187 Uiso 1 1 calc R . . H10B H 1.1961 0.2150 0.3782 0.187 Uiso 1 1 calc R . . H10C H 1.1241 0.3285 0.3834 0.187 Uiso 1 1 calc R . . C11 C 0.9208(4) 0.2705(4) 0.7027(3) 0.0673(13) Uani 1 1 d . . . H11 H 0.9011 0.2080 0.7496 0.081 Uiso 1 1 calc R . . C12 C 0.9770(4) 0.3654(4) 0.7665(3) 0.0613(12) Uani 1 1 d . . . C13 C 1.0900(4) 0.5478(4) 0.7343(3) 0.0623(12) Uani 1 1 d . . . C14 C 1.1365(4) 0.6055(5) 0.6544(4) 0.0793(15) Uani 1 1 d . . . H14 H 1.1282 0.5764 0.5894 0.095 Uiso 1 1 calc R . . C15 C 1.1955(5) 0.7069(5) 0.6707(5) 0.1016(18) Uani 1 1 d . . . H15 H 1.2276 0.7453 0.6164 0.122 Uiso 1 1 calc R . . C16 C 1.2073(4) 0.7515(5) 0.7653(5) 0.0929(17) Uani 1 1 d . . . H16 H 1.2462 0.8204 0.7760 0.112 Uiso 1 1 calc R . . C17 C 1.1607(4) 0.6930(5) 0.8447(4) 0.0902(17) Uani 1 1 d . . . H17 H 1.1694 0.7226 0.9095 0.108 Uiso 1 1 calc R . . C18 C 1.1015(4) 0.5915(5) 0.8311(3) 0.0809(15) Uani 1 1 d . . . H18 H 1.0699 0.5532 0.8856 0.097 Uiso 1 1 calc R . . H5 H 1.027(3) 0.428(3) 0.649(3) 0.055(14) Uiso 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 S1 0.1406(13) 0.0887(12) 0.0554(8) 0.0056(7) -0.0065(7) -0.0117(9) N1 0.061(3) 0.067(3) 0.063(2) -0.001(2) -0.0012(19) -0.005(2) N2 0.075(3) 0.068(3) 0.077(3) 0.000(2) -0.018(2) 0.000(2) N3 0.083(3) 0.083(3) 0.067(3) -0.012(3) 0.003(2) -0.001(3) N4 0.084(3) 0.067(3) 0.069(3) -0.010(3) -0.005(2) 0.000(3) N5 0.074(3) 0.084(4) 0.049(3) -0.007(3) -0.004(2) -0.002(2) C1 0.073(4) 0.087(5) 0.077(3) -0.010(3) -0.016(3) 0.004(4) C2 0.073(4) 0.100(5) 0.088(4) -0.019(3) -0.011(3) -0.014(4) C3 0.076(4) 0.085(5) 0.074(3) -0.005(3) 0.006(3) -0.015(4) C4 0.114(5) 0.120(6) 0.119(5) 0.011(4) -0.045(4) 0.021(4) C5 0.119(5) 0.088(5) 0.140(5) -0.003(4) 0.005(4) -0.038(4) C6 0.087(4) 0.062(4) 0.109(5) -0.011(4) -0.018(4) 0.004(3) C7 0.086(4) 0.106(6) 0.121(6) -0.040(5) 0.002(4) 0.014(4) C8 0.081(4) 0.093(5) 0.090(4) -0.036(4) -0.003(3) -0.010(4) C9 0.144(6) 0.078(5) 0.147(6) 0.006(4) -0.030(4) 0.024(4) C10 0.101(4) 0.179(7) 0.094(4) -0.048(4) 0.030(3) -0.022(4) C11 0.089(4) 0.053(3) 0.059(3) 0.002(2) 0.001(3) 0.002(3) C12 0.063(3) 0.060(4) 0.061(3) 0.005(3) 0.000(2) 0.008(3) C13 0.063(3) 0.059(4) 0.065(3) -0.008(3) -0.004(2) 0.000(3) C14 0.097(4) 0.077(4) 0.064(3) -0.006(3) -0.002(3) -0.010(3) C15 0.114(5) 0.091(5) 0.100(5) 0.010(4) 0.005(4) -0.019(4) C16 0.088(4) 0.083(5) 0.108(5) -0.014(4) -0.008(4) -0.012(3) C17 0.092(4) 0.107(5) 0.071(4) -0.016(4) -0.011(3) -0.015(4) C18 0.090(4) 0.087(4) 0.066(3) -0.015(3) -0.003(3) -0.017(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 S1 C12 1.636(4) . ? N1 N2 1.363(5) . ? N1 C3 1.372(5) . ? N1 C11 1.463(5) . ? N2 C1 1.339(5) . ? N3 C8 1.333(6) . ? N3 N4 1.377(5) . ? N4 C6 1.365(6) . ? N4 C11 1.453(5) . ? N5 C12 1.336(5) . ? N5 C13 1.428(6) . ? C1 C2 1.385(7) . ? C1 C4 1.490(7) . ? C2 C3 1.370(6) . ? C3 C5 1.478(7) . ? C6 C7 1.353(7) . ? C6 C9 1.499(7) . ? C7 C8 1.384(7) . ? C8 C10 1.487(7) . ? C11 C12 1.534(6) . ? C13 C14 1.373(6) . ? C13 C18 1.385(5) . ? C14 C15 1.380(7) . ? C15 C16 1.362(6) . ? C16 C17 1.372(6) . ? C17 C18 1.377(6) . ? 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 N2 N1 C3 113.4(4) . . ? N2 N1 C11 120.7(4) . . ? C3 N1 C11 125.2(5) . . ? N1 N2 C1 104.5(4) . . ? C8 N3 N4 104.7(5) . . ? C6 N4 N3 112.2(4) . . ? C6 N4 C11 128.9(5) . . ? N3 N4 C11 118.9(4) . . ? C12 N5 C13 133.0(4) . . ? N2 C1 C2 109.8(5) . . ? N2 C1 C4 120.3(6) . . ? C2 C1 C4 129.9(5) . . ? C1 C2 C3 109.0(5) . . ? N1 C3 C2 103.3(5) . . ? N1 C3 C5 124.3(5) . . ? C2 C3 C5 132.4(5) . . ? N4 C6 C7 104.2(5) . . ? N4 C6 C9 122.1(6) . . ? C7 C6 C9 133.6(7) . . ? C8 C7 C6 109.3(6) . . ? N3 C8 C7 109.5(5) . . ? N3 C8 C10 120.8(7) . . ? C7 C8 C10 129.8(7) . . ? N4 C11 N1 111.0(4) . . ? N4 C11 C12 114.8(4) . . ? N1 C11 C12 112.2(4) . . ? N5 C12 C11 112.5(4) . . ? N5 C12 S1 128.9(4) . . ? C11 C12 S1 118.6(4) . . ? C14 C13 C18 120.1(5) . . ? C14 C13 N5 116.2(4) . . ? C18 C13 N5 123.7(5) . . ? C15 C14 C13 120.0(5) . . ? C14 C15 C16 120.7(5) . . ? C17 C16 C15 118.9(5) . . ? C16 C17 C18 121.9(5) . . ? C17 C18 C13 118.5(5) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.181 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.041 #=======END data_6 _database_code_depnum_ccdc_archive 'CCDC 741156' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H25 N5 S' _chemical_formula_weight 319.47 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6457(13) _cell_length_b 9.4203(14) _cell_length_c 11.1657(17) _cell_angle_alpha 89.887(3) _cell_angle_beta 83.512(3) _cell_angle_gamma 75.696(2) _cell_volume 875.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.428 _exptl_crystal_size_mid 0.411 _exptl_crystal_size_min 0.154 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.190 _exptl_absorpt_correction_type Semi-empirical _exptl_absorpt_correction_T_min 0.581279 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 area detector' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4266 _diffrn_reflns_av_R_equivalents 0.0558 _diffrn_reflns_av_sigmaI/netI 0.0626 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 26.46 _reflns_number_total 2645 _reflns_number_gt 1912 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0818P)^2^+0.0000P] 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_number_reflns 2645 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0763 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1591 _refine_ls_wR_factor_gt 0.1424 _refine_ls_goodness_of_fit_ref 1.143 _refine_ls_restrained_S_all 1.143 _refine_ls_shift/su_max 0.003 _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 S1 S 0.27262(10) 0.19623(9) 0.55334(7) 0.0413(3) Uani 1 1 d . . . C3 C 0.7241(3) 0.3572(3) 0.8557(2) 0.0259(6) Uani 1 1 d . . . C2 C 0.4886(3) 0.1641(3) 0.7168(2) 0.0247(6) Uani 1 1 d . . . H2 H 0.5403 0.0818 0.6607 0.030 Uiso 1 1 calc R . . C10 C 0.2197(3) 0.1051(3) 0.9596(2) 0.0305(7) Uani 1 1 d . . . C5 C 0.7790(3) 0.1694(3) 0.7254(2) 0.0250(6) Uani 1 1 d . . . C4 C 0.8487(3) 0.2552(3) 0.7893(2) 0.0275(7) Uani 1 1 d . . . H4 H 0.9582 0.2471 0.7886 0.033 Uiso 1 1 calc R . . C12 C 0.0754(3) 0.1631(3) 1.0482(3) 0.0385(8) Uani 1 1 d . . . H12A H 0.0740 0.2607 1.0740 0.058 Uiso 1 1 calc R . . H12B H 0.0791 0.1011 1.1167 0.058 Uiso 1 1 calc R . . H12C H -0.0199 0.1650 1.0111 0.058 Uiso 1 1 calc R . . C8 C 0.4302(3) -0.0362(3) 0.8503(3) 0.0281(7) Uani 1 1 d . . . C9 C 0.3156(3) -0.0374(3) 0.9439(3) 0.0347(7) Uani 1 1 d . . . H9 H 0.3035 -0.1180 0.9888 0.042 Uiso 1 1 calc R . . C1 C 0.3666(3) 0.2711(3) 0.6485(2) 0.0261(7) Uani 1 1 d . . . C13 C 0.2336(3) 0.5429(3) 0.6331(3) 0.0319(7) Uani 1 1 d . . . C7 C 0.8538(3) 0.0493(3) 0.6343(3) 0.0354(7) Uani 1 1 d . . . H7A H 0.9679 0.0386 0.6220 0.053 Uiso 1 1 calc R . . H7B H 0.8097 0.0729 0.5596 0.053 Uiso 1 1 calc R . . H7C H 0.8321 -0.0408 0.6629 0.053 Uiso 1 1 calc R . . C6 C 0.7357(3) 0.4770(3) 0.9391(3) 0.0369(8) Uani 1 1 d . . . H6A H 0.6297 0.5295 0.9722 0.055 Uiso 1 1 calc R . . H6B H 0.7886 0.5429 0.8954 0.055 Uiso 1 1 calc R . . H6C H 0.7962 0.4355 1.0032 0.055 Uiso 1 1 calc R . . C11 C 0.5654(4) -0.1544(3) 0.7928(3) 0.0400(8) Uani 1 1 d . . . H11A H 0.5615 -0.1563 0.7073 0.060 Uiso 1 1 calc R . . H11B H 0.5565 -0.2471 0.8249 0.060 Uiso 1 1 calc R . . H11C H 0.6655 -0.1362 0.8093 0.060 Uiso 1 1 calc R . . C15 C 0.2557(4) 0.5520(4) 0.4974(3) 0.0483(9) Uani 1 1 d . . . H15A H 0.3624 0.5609 0.4713 0.072 Uiso 1 1 calc R . . H15B H 0.1789 0.6359 0.4729 0.072 Uiso 1 1 calc R . . H15C H 0.2397 0.4648 0.4617 0.072 Uiso 1 1 calc R . . C14 C 0.0639(3) 0.5359(3) 0.6797(3) 0.0444(9) Uani 1 1 d . . . H14A H 0.0407 0.4518 0.6443 0.067 Uiso 1 1 calc R . . H14B H -0.0108 0.6232 0.6583 0.067 Uiso 1 1 calc R . . H14C H 0.0546 0.5283 0.7658 0.067 Uiso 1 1 calc R . . C16 C 0.2741(4) 0.6731(3) 0.6907(3) 0.0509(9) Uani 1 1 d . . . H16A H 0.2635 0.6646 0.7768 0.076 Uiso 1 1 calc R . . H16B H 0.2018 0.7621 0.6696 0.076 Uiso 1 1 calc R . . H16C H 0.3825 0.6750 0.6622 0.076 Uiso 1 1 calc R . . N2 N 0.5820(3) 0.3376(2) 0.8362(2) 0.0265(6) Uani 1 1 d . . . N1 N 0.6173(2) 0.2210(2) 0.75554(18) 0.0233(5) Uani 1 1 d . . . N4 N 0.2720(3) 0.1949(2) 0.8809(2) 0.0301(6) Uani 1 1 d . . . N3 N 0.4023(3) 0.1052(2) 0.8146(2) 0.0262(6) Uani 1 1 d . . . N5 N 0.3482(3) 0.4110(3) 0.6746(2) 0.0266(6) Uani 1 1 d . . . H5 H 0.405(3) 0.429(3) 0.728(2) 0.025(8) Uiso 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 S1 0.0433(5) 0.0448(6) 0.0407(5) -0.0049(4) -0.0166(4) -0.0147(4) C3 0.0276(15) 0.0268(15) 0.0253(15) 0.0050(13) -0.0053(12) -0.0096(12) C2 0.0266(15) 0.0276(16) 0.0226(15) 0.0026(13) -0.0028(12) -0.0118(12) C10 0.0265(15) 0.0422(19) 0.0294(17) 0.0048(15) -0.0087(13) -0.0186(13) C5 0.0244(14) 0.0294(16) 0.0216(15) 0.0041(13) 0.0000(12) -0.0087(12) C4 0.0238(14) 0.0336(16) 0.0270(16) 0.0090(14) -0.0048(12) -0.0101(12) C12 0.0326(17) 0.054(2) 0.0331(18) 0.0065(16) -0.0024(14) -0.0188(15) C8 0.0288(15) 0.0294(16) 0.0313(17) 0.0101(14) -0.0127(13) -0.0130(12) C9 0.0352(17) 0.0406(19) 0.0369(18) 0.0157(16) -0.0129(14) -0.0222(14) C1 0.0248(14) 0.0307(17) 0.0238(15) 0.0035(14) 0.0012(12) -0.0110(12) C13 0.0278(15) 0.0300(16) 0.042(2) 0.0118(15) -0.0122(14) -0.0111(12) C7 0.0303(16) 0.0380(18) 0.0356(17) -0.0083(15) 0.0026(13) -0.0071(13) C6 0.0360(17) 0.0354(18) 0.0421(19) -0.0022(16) -0.0144(14) -0.0098(14) C11 0.0380(18) 0.0312(18) 0.053(2) 0.0080(16) -0.0123(16) -0.0093(13) C15 0.049(2) 0.058(2) 0.043(2) 0.0282(18) -0.0148(16) -0.0190(16) C14 0.0269(16) 0.0417(19) 0.064(2) 0.0052(17) -0.0064(15) -0.0068(13) C16 0.051(2) 0.036(2) 0.071(3) 0.0113(18) -0.0241(19) -0.0146(16) N2 0.0275(12) 0.0248(13) 0.0284(13) -0.0016(11) -0.0035(10) -0.0084(10) N1 0.0226(12) 0.0254(13) 0.0235(13) -0.0005(11) -0.0026(10) -0.0089(9) N4 0.0281(13) 0.0333(14) 0.0299(14) 0.0043(12) 0.0009(11) -0.0114(10) N3 0.0271(12) 0.0264(13) 0.0267(13) 0.0062(12) -0.0013(10) -0.0104(10) N5 0.0250(13) 0.0291(14) 0.0284(14) 0.0046(12) -0.0069(11) -0.0105(11) _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 S1 C1 1.664(3) . ? C3 N2 1.329(3) . ? C3 C4 1.394(4) . ? C3 C6 1.494(4) . ? C2 N3 1.441(3) . ? C2 N1 1.454(3) . ? C2 C1 1.538(4) . ? C10 N4 1.337(3) . ? C10 C9 1.392(4) . ? C10 C12 1.490(4) . ? C5 N1 1.365(3) . ? C5 C4 1.365(4) . ? C5 C7 1.492(4) . ? C8 C9 1.358(4) . ? C8 N3 1.361(3) . ? C8 C11 1.486(4) . ? C1 N5 1.317(3) . ? C13 N5 1.494(4) . ? C13 C15 1.511(4) . ? C13 C14 1.517(4) . ? C13 C16 1.519(4) . ? N2 N1 1.374(3) . ? N4 N3 1.369(3) . ? 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 N2 C3 C4 111.1(2) . . ? N2 C3 C6 120.7(2) . . ? C4 C3 C6 128.2(2) . . ? N3 C2 N1 112.6(2) . . ? N3 C2 C1 108.7(2) . . ? N1 C2 C1 115.8(2) . . ? N4 C10 C9 111.1(3) . . ? N4 C10 C12 120.0(3) . . ? C9 C10 C12 128.9(3) . . ? N1 C5 C4 105.8(2) . . ? N1 C5 C7 124.2(2) . . ? C4 C5 C7 130.0(2) . . ? C5 C4 C3 106.8(2) . . ? C9 C8 N3 105.6(2) . . ? C9 C8 C11 131.6(3) . . ? N3 C8 C11 122.8(2) . . ? C8 C9 C10 106.9(3) . . ? N5 C1 C2 115.4(2) . . ? N5 C1 S1 128.3(2) . . ? C2 C1 S1 116.3(2) . . ? N5 C13 C15 111.1(2) . . ? N5 C13 C14 108.4(2) . . ? C15 C13 C14 111.6(3) . . ? N5 C13 C16 105.3(2) . . ? C15 C13 C16 110.1(2) . . ? C14 C13 C16 110.2(3) . . ? C3 N2 N1 104.7(2) . . ? C5 N1 N2 111.7(2) . . ? C5 N1 C2 128.1(2) . . ? N2 N1 C2 120.1(2) . . ? C10 N4 N3 103.8(2) . . ? C8 N3 N4 112.5(2) . . ? C8 N3 C2 127.7(2) . . ? N4 N3 C2 119.7(2) . . ? C1 N5 C13 130.0(3) . . ? _diffrn_measured_fraction_theta_max 0.732 _diffrn_reflns_theta_full 26.46 _diffrn_measured_fraction_theta_full 0.732 _refine_diff_density_max 0.289 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.055 #===END data_8 _database_code_depnum_ccdc_archive 'CCDC 741157' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H50 Li N10 O2, C4 H8 O, Cl' _chemical_formula_sum 'C36 H58 Cl Li N10 O3' _chemical_formula_weight 721.31 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' Cl Cl 0.1484 0.1585 '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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4196(12) _cell_length_b 10.6997(13) _cell_length_c 11.0103(14) _cell_angle_alpha 66.101(7) _cell_angle_beta 79.562(8) _cell_angle_gamma 82.866(7) _cell_volume 996.2(2) _cell_formula_units_Z 1 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 828 _cell_measurement_theta_min 2.202 _cell_measurement_theta_max 18.654 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9584 _exptl_absorpt_correction_T_max 0.9844 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 area detector' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7417 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0877 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3429 _reflns_number_gt 1732 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS, XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1057P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3429 _refine_ls_number_parameters 240 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.1251 _refine_ls_R_factor_gt 0.0646 _refine_ls_wR_factor_ref 0.2023 _refine_ls_wR_factor_gt 0.1663 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.012 _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 N1 N 0.6948(3) 0.5210(3) 0.8488(3) 0.0488(9) Uani 1 1 d . . . N2 N 0.7626(3) 0.4024(3) 0.8416(3) 0.0447(9) Uani 1 1 d . . . N3 N 0.4495(3) 0.3355(3) 0.9369(3) 0.0497(9) Uani 1 1 d . . . N4 N 0.5657(3) 0.2549(3) 0.9094(3) 0.0440(8) Uani 1 1 d . . . N5 N 0.7801(3) 0.1532(3) 1.1550(3) 0.0456(9) Uani 1 1 d . . . H5 H 0.8283 0.0998 1.1165 0.055 Uiso 1 1 calc R . . O1 O 0.6219(2) 0.3385(3) 1.1226(3) 0.0492(8) Uani 1 1 d . . . Cl1 Cl 1.0000 0.0000 1.0000 0.0664(6) Uani 1 2 d S . . Li1 Li 0.5000 0.5000 1.0000 0.0341(19) Uani 1 2 d S . . C1 C 0.8734(4) 0.4274(4) 0.7389(4) 0.0474(10) Uani 1 1 d . . . C2 C 0.8802(4) 0.5659(4) 0.6808(4) 0.0518(11) Uani 1 1 d . . . H2 H 0.9480 0.6164 0.6069 0.062 Uiso 1 1 calc R . . C3 C 0.7676(4) 0.6195(4) 0.7511(4) 0.0480(11) Uani 1 1 d . . . C4 C 0.9624(4) 0.3189(4) 0.7032(4) 0.0609(12) Uani 1 1 d . . . H4A H 0.9945 0.2473 0.7842 0.091 Uiso 1 1 calc R . . H4B H 1.0469 0.3589 0.6381 0.091 Uiso 1 1 calc R . . H4C H 0.9044 0.2791 0.6639 0.091 Uiso 1 1 calc R . . C5 C 0.7242(4) 0.7656(4) 0.7285(4) 0.0614(12) Uani 1 1 d . . . H5A H 0.6316 0.7703 0.7843 0.092 Uiso 1 1 calc R . . H5B H 0.7142 0.8178 0.6337 0.092 Uiso 1 1 calc R . . H5C H 0.7983 0.8045 0.7527 0.092 Uiso 1 1 calc R . . C6 C 0.5292(4) 0.1695(4) 0.8587(4) 0.0561(11) Uani 1 1 d . . . C7 C 0.3852(5) 0.1935(4) 0.8551(5) 0.0640(13) Uani 1 1 d . . . H7 H 0.3263 0.1484 0.8257 0.077 Uiso 1 1 calc R . . C8 C 0.3394(4) 0.2964(4) 0.9024(4) 0.0517(11) Uani 1 1 d . . . C9 C 0.6362(5) 0.0752(5) 0.8138(5) 0.0738(14) Uani 1 1 d . . . H9A H 0.6942 0.1286 0.7287 0.111 Uiso 1 1 calc R . . H9B H 0.5846 0.0082 0.8014 0.111 Uiso 1 1 calc R . . H9C H 0.6999 0.0274 0.8819 0.111 Uiso 1 1 calc R . . C10 C 0.1903(4) 0.3608(5) 0.9216(5) 0.0712(14) Uani 1 1 d . . . H10A H 0.1905 0.4168 0.9733 0.107 Uiso 1 1 calc R . . H10B H 0.1217 0.2888 0.9702 0.107 Uiso 1 1 calc R . . H10C H 0.1614 0.4187 0.8338 0.107 Uiso 1 1 calc R . . C11 C 0.7062(4) 0.2721(4) 0.9342(4) 0.0447(10) Uani 1 1 d . . . H11 H 0.7746 0.1974 0.9220 0.054 Uiso 1 1 calc R . . C12 C 0.6988(4) 0.2599(4) 1.0808(4) 0.0437(10) Uani 1 1 d . . . C13 C 0.7940(4) 0.1194(4) 1.2965(4) 0.0474(10) Uani 1 1 d . . . C14 C 0.6480(4) 0.0843(4) 1.3835(4) 0.0590(12) Uani 1 1 d . . . H14A H 0.5799 0.1644 1.3560 0.089 Uiso 1 1 calc R . . H14B H 0.6587 0.0578 1.4778 0.089 Uiso 1 1 calc R . . H14C H 0.6112 0.0082 1.3729 0.089 Uiso 1 1 calc R . . C16 C 0.8996(4) -0.0066(4) 1.3382(4) 0.0650(13) Uani 1 1 d . . . H16A H 0.8587 -0.0837 1.3327 0.097 Uiso 1 1 calc R . . H16B H 0.9161 -0.0304 1.4305 0.097 Uiso 1 1 calc R . . H16C H 0.9916 0.0138 1.2779 0.097 Uiso 1 1 calc R . . C17 C 0.8532(5) 0.2381(5) 1.3088(5) 0.0670(13) Uani 1 1 d . . . H17A H 0.9433 0.2636 1.2464 0.100 Uiso 1 1 calc R . . H17B H 0.8724 0.2112 1.4009 0.100 Uiso 1 1 calc R . . H17C H 0.7824 0.3163 1.2870 0.100 Uiso 1 1 calc R . . O2 O 0.4059(10) 0.6267(11) 0.4918(10) 0.138(3) Uiso 0.50 1 d PD . . C21 C 0.3725(17) 0.5218(18) 0.483(2) 0.113(7) Uiso 0.50 1 d PD . . H21A H 0.3252 0.5574 0.4010 0.135 Uiso 0.50 1 calc PR . . H21B H 0.2942 0.4856 0.5588 0.135 Uiso 0.50 1 calc PR . . C22 C 0.4969(19) 0.5509(19) 0.552(2) 0.154(8) Uiso 0.50 1 d PD . . H22A H 0.5011 0.6503 0.4966 0.185 Uiso 0.50 1 calc PR . . H22B H 0.4846 0.5363 0.6476 0.185 Uiso 0.50 1 calc PR . . C23 C 0.5397(13) 0.6039(15) 0.5221(15) 0.099(4) Uiso 0.50 1 d PD . . H23A H 0.5348 0.5701 0.6208 0.118 Uiso 0.50 1 calc PR . . H23B H 0.5882 0.6914 0.4816 0.118 Uiso 0.50 1 calc PR . . C24 C 0.3745(18) 0.495(2) 0.524(2) 0.122(9) Uiso 0.50 1 d PD . . H24A H 0.3053 0.4503 0.6060 0.147 Uiso 0.50 1 calc PR . . H24B H 0.3225 0.5647 0.4536 0.147 Uiso 0.50 1 calc PR . . 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 0.0441(17) 0.033(2) 0.062(2) -0.0165(18) -0.0054(16) 0.0115(15) N2 0.0446(17) 0.0312(19) 0.051(2) -0.0141(16) 0.0008(15) 0.0069(14) N3 0.0462(18) 0.038(2) 0.062(2) -0.0201(18) -0.0092(16) 0.0100(15) N4 0.0479(18) 0.0316(19) 0.050(2) -0.0148(17) -0.0085(15) 0.0035(14) N5 0.0463(17) 0.035(2) 0.048(2) -0.0141(17) -0.0068(15) 0.0152(15) O1 0.0490(14) 0.0399(17) 0.0534(18) -0.0189(14) -0.0066(13) 0.0176(13) Cl1 0.0697(10) 0.0502(10) 0.0630(11) -0.0182(8) -0.0003(8) 0.0278(8) Li1 0.029(4) 0.027(5) 0.044(5) -0.012(4) -0.009(4) 0.010(3) C1 0.047(2) 0.045(3) 0.046(3) -0.017(2) -0.0018(19) 0.0016(19) C2 0.055(2) 0.039(3) 0.051(3) -0.011(2) 0.002(2) -0.002(2) C3 0.042(2) 0.036(2) 0.056(3) -0.009(2) -0.0080(19) 0.0001(19) C4 0.063(3) 0.054(3) 0.057(3) -0.022(2) 0.007(2) 0.004(2) C5 0.061(2) 0.035(3) 0.072(3) -0.008(2) -0.004(2) 0.006(2) C6 0.068(3) 0.036(3) 0.061(3) -0.016(2) -0.017(2) 0.004(2) C7 0.069(3) 0.047(3) 0.081(4) -0.025(3) -0.028(2) 0.005(2) C8 0.055(2) 0.036(3) 0.059(3) -0.012(2) -0.018(2) 0.0047(19) C9 0.083(3) 0.056(3) 0.094(4) -0.042(3) -0.020(3) 0.013(2) C10 0.054(2) 0.064(3) 0.095(4) -0.030(3) -0.021(2) 0.011(2) C11 0.051(2) 0.026(2) 0.048(3) -0.0094(19) -0.0055(19) 0.0103(17) C12 0.042(2) 0.030(2) 0.050(3) -0.010(2) -0.0034(18) 0.0070(18) C13 0.049(2) 0.042(3) 0.046(3) -0.015(2) -0.0102(19) 0.0124(18) C14 0.053(2) 0.053(3) 0.059(3) -0.014(2) -0.002(2) 0.005(2) C16 0.067(3) 0.060(3) 0.059(3) -0.019(2) -0.022(2) 0.031(2) C17 0.065(3) 0.062(3) 0.076(3) -0.027(3) -0.018(2) 0.002(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 C3 1.316(5) . ? N1 N2 1.374(4) . ? N1 Li1 2.209(3) . ? N2 C1 1.355(4) . ? N2 C11 1.449(5) . ? N3 C8 1.332(5) . ? N3 N4 1.375(4) . ? N3 Li1 2.264(3) . ? N4 C6 1.351(5) . ? N4 C11 1.446(4) . ? N5 C12 1.346(4) . ? N5 C13 1.477(5) . ? O1 C12 1.220(4) . ? O1 Li1 2.075(2) . ? Li1 O1 2.075(2) 2_667 ? Li1 N1 2.209(3) 2_667 ? Li1 N3 2.264(3) 2_667 ? C1 C2 1.360(5) . ? C1 C4 1.488(5) . ? C2 C3 1.402(5) . ? C3 C5 1.496(5) . ? C6 C7 1.354(5) . ? C6 C9 1.500(5) . ? C7 C8 1.391(6) . ? C8 C10 1.504(5) . ? C11 C12 1.554(5) . ? C13 C17 1.511(5) . ? C13 C14 1.520(5) . ? C13 C16 1.532(5) . ? O2 C21 1.248(14) . ? O2 C23 1.330(13) . ? C21 C23 1.50(2) 2_666 ? C22 C21 1.447(13) 2_666 ? C22 C24 1.495(16) . ? C23 C24 1.447(13) 2_666 ? C24 C23 1.447(13) 2_666 ? 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 C3 N1 N2 104.6(3) . . ? C3 N1 Li1 138.3(3) . . ? N2 N1 Li1 117.0(2) . . ? C1 N2 N1 112.1(3) . . ? C1 N2 C11 128.7(3) . . ? N1 N2 C11 119.1(3) . . ? C8 N3 N4 103.9(3) . . ? C8 N3 Li1 139.6(2) . . ? N4 N3 Li1 116.0(2) . . ? C6 N4 N3 112.4(3) . . ? C6 N4 C11 128.9(3) . . ? N3 N4 C11 118.6(3) . . ? C12 N5 C13 124.6(3) . . ? C12 O1 Li1 121.7(3) . . ? O1 Li1 O1 180.000(1) . 2_667 ? O1 Li1 N1 96.26(11) . 2_667 ? O1 Li1 N1 83.74(11) 2_667 2_667 ? O1 Li1 N1 83.74(11) . . ? O1 Li1 N1 96.26(11) 2_667 . ? N1 Li1 N1 180.000(1) 2_667 . ? O1 Li1 N3 98.21(11) . 2_667 ? O1 Li1 N3 81.79(11) 2_667 2_667 ? N1 Li1 N3 84.14(11) 2_667 2_667 ? N1 Li1 N3 95.86(11) . 2_667 ? O1 Li1 N3 81.79(11) . . ? O1 Li1 N3 98.21(11) 2_667 . ? N1 Li1 N3 95.86(11) 2_667 . ? N1 Li1 N3 84.14(11) . . ? N3 Li1 N3 180.000(1) 2_667 . ? N2 C1 C2 105.7(3) . . ? N2 C1 C4 124.1(4) . . ? C2 C1 C4 130.2(4) . . ? C1 C2 C3 106.5(3) . . ? N1 C3 C2 111.0(3) . . ? N1 C3 C5 119.7(3) . . ? C2 C3 C5 129.2(4) . . ? N4 C6 C7 105.6(4) . . ? N4 C6 C9 123.5(4) . . ? C7 C6 C9 130.8(4) . . ? C6 C7 C8 107.3(4) . . ? N3 C8 C7 110.7(4) . . ? N3 C8 C10 119.6(4) . . ? C7 C8 C10 129.7(4) . . ? N4 C11 N2 111.9(3) . . ? N4 C11 C12 110.6(3) . . ? N2 C11 C12 109.5(3) . . ? O1 C12 N5 124.7(4) . . ? O1 C12 C11 121.7(3) . . ? N5 C12 C11 113.6(3) . . ? N5 C13 C17 110.0(3) . . ? N5 C13 C14 109.8(3) . . ? C17 C13 C14 111.0(3) . . ? N5 C13 C16 106.4(3) . . ? C17 C13 C16 110.2(3) . . ? C14 C13 C16 109.4(3) . . ? C21 O2 C23 107.7(14) . . ? O2 C21 C23 132.1(15) . 2_666 ? C21 C22 C24 106.5(11) 2_666 . ? O2 C23 C24 113.2(12) . 2_666 ? C23 C24 C22 97.0(11) 2_666 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5 Cl1 0.88 2.31 3.167(3) 165.1 . _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.281 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.052