# 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 _publ_contact_author_name 'Albert Guijarro' _publ_contact_author_email AGUIJARRO@UA.ES _publ_section_title ; Structural Characterization and Bonding Properties of Lithium Naphthalene Radical Anion, [Li+(TMEDA)2][C10H8*-], and Lithium Naphthalene Dianion [(Li+TMEDA)2C10H8-2]. ; loop_ _publ_author_name 'Albert Guijarro' 'Cristobal Melero' 'Miguel Yus' # Attachment 'Compound_1.cif' # Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_Compound_1 _database_code_depnum_ccdc_archive 'CCDC 695890' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H40 Li N4' _chemical_formula_sum 'C22 H40 Li N4' _chemical_formula_weight 367.52 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' Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.6106(19) _cell_length_b 9.2603(11) _cell_length_c 16.937(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.232(2) _cell_angle_gamma 90.00 _cell_volume 2338.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 2641 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 24.8 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.044 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 812 _exptl_absorpt_coefficient_mu 0.061 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.895 _exptl_absorpt_correction_T_max 0.976 _exptl_absorpt_process_details 'Bruker/Siemens SADABS V2.03' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(1) _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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9464 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2057 _reflns_number_gt 1673 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART V5.625' _computing_cell_refinement 'Bruker SMART V5.625' _computing_data_reduction 'Bruker SAINT V6.28A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL Rel. 6.12/V (Siemens, 1996)' _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^)+(0.1461P)^2^+2.0075P] 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_number_reflns 2057 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0823 _refine_ls_R_factor_gt 0.0699 _refine_ls_wR_factor_ref 0.2348 _refine_ls_wR_factor_gt 0.2165 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _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 Li1 Li 0.5000 0.0460(5) 0.2500 0.0276(10) Uani 1 2 d S . . N1 N 0.43198(13) 0.2097(2) 0.29577(12) 0.0394(6) Uani 1 1 d . . . C1 C 0.3429(2) 0.2238(4) 0.2387(2) 0.0650(9) Uani 1 1 d . . . H1A H 0.3064 0.1446 0.2463 0.098 Uiso 1 1 calc R . . H1B H 0.3463 0.2230 0.1831 0.098 Uiso 1 1 calc R . . H1C H 0.3168 0.3131 0.2489 0.098 Uiso 1 1 calc R . . C2 C 0.4254(2) 0.2007(3) 0.38015(16) 0.0542(8) Uani 1 1 d . . . H2A H 0.3929 0.2828 0.3909 0.081 Uiso 1 1 calc R . . H2B H 0.4845 0.1997 0.4187 0.081 Uiso 1 1 calc R . . H2C H 0.3944 0.1138 0.3861 0.081 Uiso 1 1 calc R . . C3 C 0.4859(2) 0.3392(3) 0.2885(2) 0.0600(8) Uani 1 1 d . . . H3A H 0.5389 0.3432 0.3361 0.072 Uiso 1 1 calc R . . H3B H 0.4507 0.4253 0.2892 0.072 Uiso 1 1 calc R . . N2 N 0.57098(14) -0.1160(2) 0.33109(11) 0.0400(6) Uani 1 1 d . . . C4 C 0.6619(2) -0.1348(4) 0.3270(2) 0.0693(10) Uani 1 1 d . . . H4A H 0.6968 -0.0507 0.3491 0.104 Uiso 1 1 calc R . . H4B H 0.6608 -0.1479 0.2705 0.104 Uiso 1 1 calc R . . H4C H 0.6883 -0.2181 0.3587 0.104 Uiso 1 1 calc R . . C5 C 0.5754(2) -0.1018(3) 0.41856(15) 0.0479(7) Uani 1 1 d . . . H5A H 0.6065 -0.1834 0.4488 0.072 Uiso 1 1 calc R . . H5B H 0.5158 -0.0979 0.4235 0.072 Uiso 1 1 calc R . . H5C H 0.6070 -0.0148 0.4406 0.072 Uiso 1 1 calc R . . C6 C 0.5144(2) -0.2448(3) 0.29639(16) 0.0532(8) Uani 1 1 d . . . H6A H 0.4616 -0.2448 0.3155 0.064 Uiso 1 1 calc R . . H6B H 0.5481 -0.3321 0.3165 0.064 Uiso 1 1 calc R . . C7 C 0.73856(14) 0.1978(2) 0.52700(13) 0.0331(6) Uani 1 1 d . . . C8 C 0.78729(16) 0.0670(3) 0.54245(15) 0.0413(6) Uani 1 1 d . . . H8 H 0.7740 -0.0004 0.5778 0.050 Uiso 1 1 calc R . . C9 C 0.85466(17) 0.0360(3) 0.50632(16) 0.0450(7) Uani 1 1 d . . . H9 H 0.8848 -0.0519 0.5170 0.054 Uiso 1 1 calc R . . C10 C 0.87681(16) 0.1356(3) 0.45468(15) 0.0433(7) Uani 1 1 d . . . H10 H 0.9218 0.1150 0.4307 0.052 Uiso 1 1 calc R . . C11 C 0.83122(16) 0.2672(3) 0.43883(15) 0.0410(6) Uani 1 1 d . . . H11 H 0.8473 0.3340 0.4047 0.049 Uiso 1 1 calc R . . 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 Li1 0.029(2) 0.030(2) 0.024(2) 0.000 0.0086(19) 0.000 N1 0.0433(11) 0.0443(12) 0.0342(11) -0.0005(8) 0.0168(9) 0.0095(9) C1 0.0509(17) 0.083(2) 0.0612(18) 0.0049(16) 0.0166(14) 0.0219(16) C2 0.0695(18) 0.0592(18) 0.0420(15) -0.0051(12) 0.0287(13) 0.0100(14) C3 0.0694(19) 0.0387(15) 0.085(2) -0.0136(14) 0.0429(17) -0.0043(13) N2 0.0472(12) 0.0405(12) 0.0315(10) 0.0052(8) 0.0105(8) 0.0089(9) C4 0.0573(18) 0.092(2) 0.0643(19) 0.0259(17) 0.0266(15) 0.0296(17) C5 0.0581(16) 0.0505(16) 0.0320(13) 0.0042(11) 0.0084(11) -0.0001(12) C6 0.0767(19) 0.0362(14) 0.0455(16) 0.0036(11) 0.0165(14) -0.0020(13) C7 0.0317(11) 0.0350(12) 0.0287(11) -0.0048(9) 0.0032(9) -0.0043(9) C8 0.0466(13) 0.0360(13) 0.0404(13) 0.0023(10) 0.0115(11) 0.0006(10) C9 0.0442(14) 0.0402(14) 0.0467(14) -0.0047(11) 0.0075(11) 0.0104(11) C10 0.0370(13) 0.0529(15) 0.0410(13) -0.0077(11) 0.0129(10) 0.0040(11) C11 0.0404(13) 0.0471(14) 0.0385(13) 0.0017(10) 0.0162(10) -0.0013(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 Li1 N2 2.113(4) . ? Li1 N1 2.125(4) . ? N1 C1 1.445(4) . ? N1 C2 1.465(3) . ? N1 C3 1.491(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C3 1.495(6) 2_655 ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? N2 C4 1.452(4) . ? N2 C5 1.468(3) . ? N2 C6 1.497(4) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C6 1.501(5) 2_655 ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.413(3) . ? C7 C11 1.414(3) 7_656 ? C7 C7 1.446(4) 7_656 ? C8 C9 1.394(3) . ? C8 H8 0.9300 . ? C9 C10 1.384(4) . ? C9 H9 0.9300 . ? C10 C11 1.397(4) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? 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 Li1 N2 89.5(2) 2_655 . ? N2 Li1 N1 121.42(8) 2_655 . ? N2 Li1 N1 119.47(7) . . ? N1 Li1 N1 89.0(2) 2_655 . ? C1 N1 C2 109.0(2) . . ? C1 N1 C3 109.1(2) . . ? C2 N1 C3 109.3(2) . . ? C1 N1 Li1 107.84(17) . . ? C2 N1 Li1 120.18(17) . . ? C3 N1 Li1 100.86(17) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 C3 113.1(2) . 2_655 ? N1 C3 H3A 109.0 . . ? C3 C3 H3A 109.0 2_655 . ? N1 C3 H3B 109.0 . . ? C3 C3 H3B 109.0 2_655 . ? H3A C3 H3B 107.8 . . ? C4 N2 C5 107.7(2) . . ? C4 N2 C6 111.0(2) . . ? C5 N2 C6 108.28(19) . . ? C4 N2 Li1 112.69(17) . . ? C5 N2 Li1 116.82(17) . . ? C6 N2 Li1 100.10(17) . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N2 C5 H5A 109.5 . . ? N2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 C6 111.69(19) . 2_655 ? N2 C6 H6A 109.3 . . ? C6 C6 H6A 109.3 2_655 . ? N2 C6 H6B 109.3 . . ? C6 C6 H6B 109.3 2_655 . ? H6A C6 H6B 107.9 . . ? C8 C7 C11 123.9(2) . 7_656 ? C8 C7 C7 118.0(3) . 7_656 ? C11 C7 C7 118.0(3) 7_656 7_656 ? C9 C8 C7 122.0(2) . . ? C9 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? C10 C9 C8 120.1(2) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 119.6(2) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C10 C11 C7 122.1(2) . 7_656 ? C10 C11 H11 118.9 . . ? C7 C11 H11 118.9 7_656 . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.616 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.058 # Attachment 'Compound_2.cif' # Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_Compound_2 _database_code_depnum_ccdc_archive 'CCDC 695891' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H40 Li2 N4, C6 H6' _chemical_formula_sum 'C28 H46 Li2 N4' _chemical_formula_weight 452.57 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' 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 8.7009(9) _cell_length_b 9.0075(9) _cell_length_c 10.1014(11) _cell_angle_alpha 101.930(2) _cell_angle_beta 98.277(2) _cell_angle_gamma 109.538(2) _cell_volume 710.22(13) _cell_formula_units_Z 1 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 3511 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 27.45 _exptl_crystal_description block _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.42 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.058 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 248 _exptl_absorpt_coefficient_mu 0.061 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.907 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details 'Bruker/Siemens SADABS V2.03' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(1) _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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7324 _diffrn_reflns_av_R_equivalents 0.0173 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _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 2.12 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3261 _reflns_number_gt 2837 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART V5.625' _computing_cell_refinement 'Bruker SMART V5.625' _computing_data_reduction 'Bruker SAINT V6.28A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL Rel. 6.12/V (Siemens, 1996)' _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^)+(0.0748P)^2^+0.1627P] 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_number_reflns 3261 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1363 _refine_ls_wR_factor_gt 0.1300 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.002 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 Li1 Li 0.8323(2) 0.0678(2) 0.1687(2) 0.0305(4) Uani 1 1 d . . . N1 N 0.76449(12) 0.14517(12) 0.35712(10) 0.0300(2) Uani 1 1 d . . . C1 C 0.58511(17) 0.05332(17) 0.33490(16) 0.0429(3) Uani 1 1 d . . . H1A H 0.5652 -0.0600 0.3267 0.064 Uiso 1 1 calc R . . H1B H 0.5268 0.0634 0.2511 0.064 Uiso 1 1 calc R . . H1C H 0.5454 0.0961 0.4123 0.064 Uiso 1 1 calc R . . C2 C 0.8533(2) 0.1240(2) 0.48116(15) 0.0525(4) Uani 1 1 d . . . H2A H 0.8154 0.1651 0.5604 0.079 Uiso 1 1 calc R . . H2B H 0.9715 0.1830 0.4953 0.079 Uiso 1 1 calc R . . H2C H 0.8315 0.0097 0.4696 0.079 Uiso 1 1 calc R . . C3 C 0.79959(16) 0.31994(15) 0.37283(13) 0.0356(3) Uani 1 1 d . . . H3A H 0.9189 0.3816 0.4092 0.043 Uiso 1 1 calc R . . H3B H 0.7415 0.3575 0.4394 0.043 Uiso 1 1 calc R . . C4 C 0.74517(15) 0.35271(14) 0.23664(13) 0.0329(3) Uani 1 1 d . . . H4A H 0.6240 0.3029 0.2061 0.040 Uiso 1 1 calc R . . H4B H 0.7783 0.4698 0.2501 0.040 Uiso 1 1 calc R . . N2 N 0.81997(12) 0.28707(12) 0.12936(10) 0.0284(2) Uani 1 1 d . . . C5 C 0.99465(15) 0.39449(16) 0.14775(15) 0.0393(3) Uani 1 1 d . . . H5A H 0.9997 0.5011 0.1424 0.059 Uiso 1 1 calc R . . H5B H 1.0408 0.3496 0.0760 0.059 Uiso 1 1 calc R . . H5C H 1.0581 0.4032 0.2370 0.059 Uiso 1 1 calc R . . C6 C 0.72505(18) 0.26933(18) -0.00847(14) 0.0411(3) Uani 1 1 d . . . H6A H 0.6112 0.1961 -0.0219 0.062 Uiso 1 1 calc R . . H6B H 0.7747 0.2258 -0.0781 0.062 Uiso 1 1 calc R . . H6C H 0.7269 0.3744 -0.0160 0.062 Uiso 1 1 calc R . . C7 C 1.07203(12) 0.02341(12) 0.05734(10) 0.0232(2) Uani 1 1 d . . . C8 C 1.04363(14) -0.03393(14) 0.17600(11) 0.0279(2) Uani 1 1 d . . . H8 H 1.1263 0.0128 0.2582 0.033 Uiso 1 1 calc R . . C9 C 0.88991(15) -0.16256(14) 0.17136(12) 0.0310(3) Uani 1 1 d . . . H9 H 0.8825 -0.2164 0.2409 0.037 Uiso 1 1 calc R . . C10 C 0.75479(14) -0.20536(14) 0.06437(13) 0.0313(3) Uani 1 1 d . . . H10 H 0.6539 -0.2874 0.0609 0.038 Uiso 1 1 calc R . . C11 C 0.76980(13) -0.12238(13) -0.04300(11) 0.0281(2) Uani 1 1 d . . . H11 H 0.6734 -0.1340 -0.1045 0.034 Uiso 1 1 calc R . . C12 C 0.4139(2) 0.37983(19) 0.5541(2) 0.0572(4) Uani 1 1 d . . . H12 H 0.3552 0.2976 0.5910 0.069 Uiso 1 1 calc R . . C13 C 0.36000(18) 0.37187(19) 0.41764(19) 0.0550(4) Uani 1 1 d . . . H13 H 0.2648 0.2846 0.3625 0.066 Uiso 1 1 calc R . . C14 C 0.4450(2) 0.4908(2) 0.36265(18) 0.0552(4) Uani 1 1 d . . . H14 H 0.4089 0.4855 0.2699 0.066 Uiso 1 1 calc R . . 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 Li1 0.0333(10) 0.0304(10) 0.0314(10) 0.0081(8) 0.0105(8) 0.0156(8) N1 0.0338(5) 0.0339(5) 0.0262(5) 0.0089(4) 0.0076(4) 0.0170(4) C1 0.0405(7) 0.0414(7) 0.0519(8) 0.0199(6) 0.0166(6) 0.0149(6) C2 0.0642(10) 0.0703(10) 0.0340(7) 0.0186(7) 0.0070(6) 0.0382(8) C3 0.0414(7) 0.0314(6) 0.0317(6) 0.0006(5) 0.0123(5) 0.0141(5) C4 0.0359(6) 0.0284(6) 0.0431(7) 0.0118(5) 0.0188(5) 0.0176(5) N2 0.0292(5) 0.0302(5) 0.0316(5) 0.0113(4) 0.0120(4) 0.0147(4) C5 0.0321(6) 0.0408(7) 0.0503(7) 0.0174(6) 0.0169(5) 0.0143(5) C6 0.0448(7) 0.0481(7) 0.0383(7) 0.0163(6) 0.0100(5) 0.0244(6) C7 0.0234(5) 0.0234(5) 0.0232(5) 0.0022(4) 0.0044(4) 0.0122(4) C8 0.0302(5) 0.0327(6) 0.0230(5) 0.0065(4) 0.0044(4) 0.0159(5) C9 0.0399(6) 0.0304(6) 0.0322(6) 0.0136(4) 0.0157(5) 0.0191(5) C10 0.0296(6) 0.0253(5) 0.0392(6) 0.0072(4) 0.0144(5) 0.0091(4) C11 0.0220(5) 0.0298(5) 0.0294(5) 0.0026(4) 0.0035(4) 0.0102(4) C12 0.0521(9) 0.0441(8) 0.0910(13) 0.0209(8) 0.0358(9) 0.0279(7) C13 0.0354(7) 0.0407(8) 0.0732(11) -0.0151(7) 0.0059(7) 0.0159(6) C14 0.0534(9) 0.0687(10) 0.0517(9) 0.0051(7) 0.0132(7) 0.0396(8) _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 Li1 N1 2.123(2) . ? Li1 N2 2.128(2) . ? Li1 C10 2.287(2) . ? Li1 C9 2.296(2) . ? Li1 C11 2.309(2) . ? Li1 C8 2.311(2) . ? Li1 C7 2.610(2) 2_755 ? Li1 C7 2.612(2) . ? N1 C2 1.4567(16) . ? N1 C1 1.4593(16) . ? N1 C3 1.4690(16) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.5092(18) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N2 1.4640(14) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? N2 C6 1.4610(16) . ? N2 C5 1.4634(15) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C11 1.4142(15) 2_755 ? C7 C8 1.4214(15) . ? C7 C7 1.4552(19) 2_755 ? C8 C9 1.4341(16) . ? C8 H8 0.9300 . ? C9 C10 1.3630(17) . ? C9 H9 0.9300 . ? C10 C11 1.4362(16) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.369(3) . ? C12 C14 1.383(2) 2_666 ? C12 H12 0.9300 . ? C13 C14 1.356(3) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? 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 N1 Li1 N2 85.24(8) . . ? N1 Li1 C10 120.13(10) . . ? N2 Li1 C10 142.05(10) . . ? N1 Li1 C9 108.43(9) . . ? N2 Li1 C9 165.12(10) . . ? C10 Li1 C9 34.60(5) . . ? N1 Li1 C11 149.09(10) . . ? N2 Li1 C11 107.88(9) . . ? C10 Li1 C11 36.41(5) . . ? C9 Li1 C11 63.30(6) . . ? N1 Li1 C8 118.51(9) . . ? N2 Li1 C8 131.89(10) . . ? C10 Li1 C8 63.41(6) . . ? C9 Li1 C8 36.27(5) . . ? C11 Li1 C8 73.77(7) . . ? N1 Li1 C7 177.73(10) . 2_755 ? N2 Li1 C7 95.22(8) . 2_755 ? C10 Li1 C7 60.60(6) . 2_755 ? C9 Li1 C7 70.88(6) . 2_755 ? C11 Li1 C7 32.69(4) . 2_755 ? C8 Li1 C7 59.62(6) . 2_755 ? N1 Li1 C7 145.39(10) . . ? N2 Li1 C7 104.90(8) . . ? C10 Li1 C7 71.09(6) . . ? C9 Li1 C7 60.52(6) . . ? C11 Li1 C7 59.54(6) . . ? C8 Li1 C7 32.84(4) . . ? C7 Li1 C7 32.36(5) 2_755 . ? C2 N1 C1 109.31(11) . . ? C2 N1 C3 109.87(11) . . ? C1 N1 C3 110.84(10) . . ? C2 N1 Li1 116.24(10) . . ? C1 N1 Li1 106.58(9) . . ? C3 N1 Li1 103.85(9) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 C4 111.99(10) . . ? N1 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? N1 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? N2 C4 C3 111.32(9) . . ? N2 C4 H4A 109.4 . . ? C3 C4 H4A 109.4 . . ? N2 C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C6 N2 C5 109.36(10) . . ? C6 N2 C4 110.04(9) . . ? C5 N2 C4 110.92(10) . . ? C6 N2 Li1 115.81(9) . . ? C5 N2 Li1 104.86(9) . . ? C4 N2 Li1 105.72(8) . . ? N2 C5 H5A 109.5 . . ? N2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C11 C7 C8 124.61(10) 2_755 . ? C11 C7 C7 117.84(12) 2_755 2_755 ? C8 C7 C7 117.55(12) . 2_755 ? C11 C7 Li1 61.87(7) 2_755 2_755 ? C8 C7 Li1 136.89(8) . 2_755 ? C7 C7 Li1 73.90(9) 2_755 2_755 ? C11 C7 Li1 136.99(8) 2_755 . ? C8 C7 Li1 61.85(7) . . ? C7 C7 Li1 73.74(9) 2_755 . ? Li1 C7 Li1 147.64(5) 2_755 . ? C7 C8 C9 121.24(10) . . ? C7 C8 Li1 85.31(8) . . ? C9 C8 Li1 71.29(8) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? Li1 C8 H8 114.2 . . ? C10 C9 C8 119.52(10) . . ? C10 C9 Li1 72.36(8) . . ? C8 C9 Li1 72.44(8) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? Li1 C9 H9 126.9 . . ? C9 C10 C11 119.32(10) . . ? C9 C10 Li1 73.04(8) . . ? C11 C10 Li1 72.61(8) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? Li1 C10 H10 125.8 . . ? C7 C11 C10 121.46(10) 2_755 . ? C7 C11 Li1 85.44(8) 2_755 . ? C10 C11 Li1 70.97(8) . . ? C7 C11 H11 119.3 2_755 . ? C10 C11 H11 119.3 . . ? Li1 C11 H11 114.5 . . ? C13 C12 C14 120.52(16) . 2_666 ? C13 C12 H12 119.7 . . ? C14 C12 H12 119.7 2_666 . ? C14 C13 C12 120.20(15) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C12 119.28(16) . 2_666 ? C13 C14 H14 120.4 . . ? C12 C14 H14 120.4 2_666 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.292 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.049