Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Kenneth Henderson' _publ_contact_author_address ; Department of Chemistry and Biochemistry University of Notre Dame 251 Nieuwland Science Hall Notre Dame IN 46556-5670 UNITED STATES OF AMERICA ; _publ_contact_author_email KHENDERS@ND.EDU _publ_section_title ; 4 Methoxy- and 4 cyano-substituted lithium aryloxides: electronic effects of substituents on aggregation ; loop_ _publ_author_name 'K. Henderson' 'A. R. Kennedy' 'Dugald J. MacDougall' 'Bruce C. Noll' data_hend23 _database_code_depnum_ccdc_archive 'CCDC 287368' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'lithium 4-cyanophenoxide pyridine' _chemical_melting_point ? _chemical_formula_moiety 'C34 H28 Li2 N6 O2, C5 H5 N' _chemical_formula_sum 'C39 H33 Li2 N7 O2' _chemical_formula_weight 645.60 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Li Li -0.0003 0.0001 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 26.4622(9) _cell_length_b 9.1840(5) _cell_length_c 17.4818(9) _cell_angle_alpha 90.00 _cell_angle_beta 122.969(2) _cell_angle_gamma 90.00 _cell_volume 3564.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 3252 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description needle _exptl_crystal_colour 'clear colorless' _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.203 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1352 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _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 'Nonius Kappa CCD' _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 6016 _diffrn_reflns_av_R_equivalents 0.0574 _diffrn_reflns_av_sigmaI/netI 0.0781 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 24.95 _reflns_number_total 3323 _reflns_number_gt 2221 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Denzo & Collect' _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Pyridine group of N8 is probably disordered or not 100 percent occupied. However, no better model was found than that reported. 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^)+(0.0508P)^2^+5.5440P] 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 3323 _refine_ls_number_parameters 437 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1142 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.1474 _refine_ls_wR_factor_gt 0.1268 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 Li1 Li 0.2172(4) 0.9940(11) 0.2752(6) 0.036(2) Uani 1 1 d . . . Li2 Li 0.2684(4) 0.8900(12) 0.1918(6) 0.034(2) Uani 1 1 d . . . O1 O 0.19918(15) 1.0043(4) 0.1546(2) 0.0348(10) Uani 1 1 d . . . O2 O 0.28603(16) 0.8780(4) 0.3144(2) 0.0343(10) Uani 1 1 d . . . N1 N -0.0448(2) 1.3025(6) -0.2113(3) 0.0417(13) Uani 1 1 d . . . N2 N 0.5298(2) 0.6051(7) 0.6922(3) 0.0466(15) Uani 1 1 d . . . N3 N 0.2340(2) 1.2007(6) 0.3326(3) 0.0364(12) Uani 1 1 d . . . N4 N 0.1588(2) 0.8829(6) 0.3005(3) 0.0357(13) Uani 1 1 d . . . N5 N 0.2402(2) 0.6970(6) 0.1193(3) 0.0384(13) Uani 1 1 d . . . N6 N 0.3378(2) 0.9971(6) 0.1925(3) 0.0378(13) Uani 1 1 d . . . N7 N 0.0000 0.5611(9) 0.0000 0.051(2) Uani 1 2 d S . . C1 C 0.1519(2) 1.0608(6) 0.0828(3) 0.0279(14) Uani 1 1 d . . . C2 C 0.1171(2) 1.1688(6) 0.0908(3) 0.0293(14) Uani 1 1 d . . . H2 H 0.1282 1.1987 0.1500 0.035 Uiso 1 1 calc R . . C3 C 0.0683(2) 1.2321(7) 0.0169(4) 0.0329(14) Uani 1 1 d . . . H3 H 0.0467 1.3065 0.0251 0.040 Uiso 1 1 calc R . . C4 C 0.0499(2) 1.1867(6) -0.0719(4) 0.0296(14) Uani 1 1 d . . . C5 C 0.0824(2) 1.0778(7) -0.0824(4) 0.0348(15) Uani 1 1 d . . . H5 H 0.0700 1.0453 -0.1417 0.042 Uiso 1 1 calc R . . C6 C 0.1322(2) 1.0172(7) -0.0075(4) 0.0344(15) Uani 1 1 d . . . H6 H 0.1541 0.9443 -0.0161 0.041 Uiso 1 1 calc R . . C7 C -0.0031(3) 1.2505(7) -0.1505(4) 0.0359(15) Uani 1 1 d . . . C8 C 0.3333(2) 0.8254(6) 0.3879(3) 0.0270(14) Uani 1 1 d . . . C9 C 0.3723(2) 0.7272(7) 0.3843(4) 0.0327(14) Uani 1 1 d . . . H9 H 0.3647 0.6996 0.3266 0.039 Uiso 1 1 calc R . . C10 C 0.4218(2) 0.6688(7) 0.4626(3) 0.0326(15) Uani 1 1 d . . . H10 H 0.4472 0.6015 0.4578 0.039 Uiso 1 1 calc R . . C11 C 0.4343(2) 0.7086(7) 0.5479(3) 0.0339(14) Uani 1 1 d . . . C12 C 0.3963(2) 0.8046(7) 0.5547(4) 0.0353(15) Uani 1 1 d . . . H12 H 0.4043 0.8310 0.6128 0.042 Uiso 1 1 calc R . . C13 C 0.3465(2) 0.8619(6) 0.4760(3) 0.0306(14) Uani 1 1 d . . . H13 H 0.3207 0.9271 0.4813 0.037 Uiso 1 1 calc R . . C14 C 0.4876(3) 0.6512(7) 0.6290(4) 0.0365(15) Uani 1 1 d . . . C15 C 0.2422(3) 1.2390(7) 0.4111(4) 0.0384(15) Uani 1 1 d . . . H15 H 0.2294 1.1726 0.4389 0.046 Uiso 1 1 calc R . . C16 C 0.2678(3) 1.3671(7) 0.4559(4) 0.0406(16) Uani 1 1 d . . . H16 H 0.2725 1.3887 0.5126 0.049 Uiso 1 1 calc R . . C17 C 0.2864(3) 1.4629(7) 0.4160(4) 0.0405(16) Uani 1 1 d . . . H17 H 0.3064 1.5504 0.4464 0.049 Uiso 1 1 calc R . . C18 C 0.2760(3) 1.4320(8) 0.3323(4) 0.0471(17) Uani 1 1 d . . . H18 H 0.2867 1.4993 0.3021 0.057 Uiso 1 1 calc R . . C19 C 0.2493(3) 1.2991(8) 0.2923(4) 0.0482(17) Uani 1 1 d . . . H19 H 0.2417 1.2773 0.2338 0.058 Uiso 1 1 calc R . . C20 C 0.1665(3) 0.7381(7) 0.3078(4) 0.0385(16) Uani 1 1 d . . . H20 H 0.1947 0.6972 0.2963 0.046 Uiso 1 1 calc R . . C21 C 0.1363(3) 0.6453(8) 0.3306(4) 0.0438(17) Uani 1 1 d . . . H21 H 0.1435 0.5435 0.3342 0.053 Uiso 1 1 calc R . . C22 C 0.0952(3) 0.7015(8) 0.3485(4) 0.0470(17) Uani 1 1 d . . . H22 H 0.0742 0.6403 0.3660 0.056 Uiso 1 1 calc R . . C23 C 0.0859(3) 0.8498(7) 0.3400(4) 0.0420(17) Uani 1 1 d . . . H23 H 0.0576 0.8927 0.3506 0.050 Uiso 1 1 calc R . . C24 C 0.1179(3) 0.9362(7) 0.3160(4) 0.0424(17) Uani 1 1 d . . . H24 H 0.1107 1.0381 0.3101 0.051 Uiso 1 1 calc R . . C25 C 0.2665(3) 0.6036(8) 0.0928(4) 0.0431(16) Uani 1 1 d . . . H25 H 0.3056 0.6259 0.1065 0.052 Uiso 1 1 calc R . . C26 C 0.2396(3) 0.4764(7) 0.0466(4) 0.0416(16) Uani 1 1 d . . . H26 H 0.2598 0.4139 0.0284 0.050 Uiso 1 1 calc R . . C27 C 0.1836(3) 0.4407(8) 0.0271(4) 0.0433(16) Uani 1 1 d . . . H27 H 0.1649 0.3518 -0.0028 0.052 Uiso 1 1 calc R . . C28 C 0.1550(3) 0.5359(7) 0.0518(4) 0.0480(18) Uani 1 1 d . . . H28 H 0.1156 0.5155 0.0379 0.058 Uiso 1 1 calc R . . C29 C 0.1842(3) 0.6613(7) 0.0968(4) 0.0433(16) Uani 1 1 d . . . H29 H 0.1638 0.7270 0.1130 0.052 Uiso 1 1 calc R . . C30 C 0.3301(3) 1.1412(8) 0.1780(4) 0.0477(18) Uani 1 1 d . . . H30 H 0.2922 1.1812 0.1609 0.057 Uiso 1 1 calc R . . C31 C 0.3734(3) 1.2346(8) 0.1861(5) 0.059(2) Uani 1 1 d . . . H31 H 0.3660 1.3363 0.1771 0.070 Uiso 1 1 calc R . . C32 C 0.4276(3) 1.1772(8) 0.2077(5) 0.058(2) Uani 1 1 d . . . H32 H 0.4581 1.2382 0.2119 0.070 Uiso 1 1 calc R . . C33 C 0.4370(3) 1.0297(9) 0.2229(5) 0.057(2) Uani 1 1 d . . . H33 H 0.4742 0.9872 0.2386 0.069 Uiso 1 1 calc R . . C34 C 0.3914(3) 0.9448(8) 0.2149(4) 0.0427(17) Uani 1 1 d . . . H34 H 0.3984 0.8433 0.2260 0.051 Uiso 1 1 calc R . . C35 C 0.0190(3) 0.6378(7) 0.0755(5) 0.0490(18) Uani 1 1 d . . . H35 H 0.0332 0.5863 0.1307 0.059 Uiso 1 1 calc R . . C36 C 0.0193(3) 0.7868(8) 0.0782(5) 0.057(2) Uani 1 1 d . . . H36 H 0.0327 0.8373 0.1335 0.069 Uiso 1 1 calc R . . C37 C 0.0000 0.8600(10) 0.0000 0.048(3) Uani 1 2 d S . . H37 H 0.0000 0.9634 0.0000 0.058 Uiso 1 2 calc SR . . N8 N 0.5000 0.3470(12) 0.5000 0.085(3) Uiso 1 2 d S . . C40 C 0.4487(5) 0.2686(11) 0.4548(7) 0.094(3) Uiso 1 1 d . . . H40 H 0.4113 0.3189 0.4243 0.113 Uiso 1 1 calc R . . C39 C 0.4481(5) 0.1162(13) 0.4507(7) 0.115(4) Uiso 1 1 d . . . H39 H 0.4120 0.0623 0.4141 0.138 Uiso 1 1 calc R . . C38 C 0.5000 0.054(2) 0.5000 0.131(6) Uiso 1 2 d S . . H38 H 0.5000 -0.0494 0.5000 0.157 Uiso 1 2 calc SR . . 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 0.037(5) 0.035(6) 0.030(5) -0.010(5) 0.014(4) -0.005(5) Li2 0.039(5) 0.038(6) 0.027(5) 0.002(5) 0.019(4) 0.003(5) O1 0.028(2) 0.041(3) 0.030(2) 0.005(2) 0.0119(18) 0.010(2) O2 0.032(2) 0.036(2) 0.028(2) 0.0041(19) 0.0113(18) 0.0029(19) N1 0.040(3) 0.048(3) 0.030(3) 0.003(3) 0.014(2) 0.008(3) N2 0.038(3) 0.064(4) 0.029(3) 0.006(3) 0.013(3) 0.001(3) N3 0.043(3) 0.033(3) 0.037(3) -0.006(3) 0.024(2) -0.003(3) N4 0.037(3) 0.031(3) 0.032(3) 0.002(2) 0.015(2) 0.003(3) N5 0.040(3) 0.037(3) 0.037(3) -0.002(3) 0.020(2) -0.004(3) N6 0.034(3) 0.041(4) 0.038(3) -0.002(3) 0.020(2) 0.001(3) N7 0.056(5) 0.029(5) 0.070(6) 0.000 0.035(5) 0.000 C1 0.026(3) 0.035(4) 0.021(3) -0.001(3) 0.011(3) -0.001(3) C2 0.029(3) 0.034(4) 0.026(3) -0.003(3) 0.016(3) -0.001(3) C3 0.026(3) 0.038(4) 0.034(3) 0.000(3) 0.015(3) 0.004(3) C4 0.026(3) 0.028(4) 0.031(3) 0.006(3) 0.013(2) 0.002(3) C5 0.032(3) 0.043(4) 0.024(3) -0.002(3) 0.013(3) 0.000(3) C6 0.034(3) 0.034(4) 0.034(3) 0.000(3) 0.017(3) 0.006(3) C7 0.035(3) 0.033(4) 0.034(3) 0.004(3) 0.016(3) -0.002(3) C8 0.025(3) 0.027(3) 0.026(3) 0.008(3) 0.011(3) 0.001(3) C9 0.033(3) 0.033(3) 0.028(3) -0.002(3) 0.014(3) -0.001(3) C10 0.029(3) 0.039(4) 0.031(3) -0.002(3) 0.017(3) 0.004(3) C11 0.033(3) 0.034(4) 0.026(3) 0.003(3) 0.010(3) -0.001(3) C12 0.038(3) 0.038(4) 0.030(3) 0.004(3) 0.019(3) 0.003(3) C13 0.033(3) 0.030(3) 0.028(3) 0.004(3) 0.016(3) 0.004(3) C14 0.038(3) 0.043(4) 0.031(3) 0.001(3) 0.021(3) -0.005(3) C15 0.049(4) 0.036(4) 0.039(4) -0.002(3) 0.031(3) -0.008(3) C16 0.048(4) 0.043(4) 0.034(3) -0.006(3) 0.025(3) 0.002(3) C17 0.040(3) 0.035(4) 0.043(4) -0.014(3) 0.020(3) -0.012(3) C18 0.052(4) 0.051(4) 0.040(4) -0.005(3) 0.027(3) -0.018(4) C19 0.054(4) 0.055(4) 0.038(4) -0.007(4) 0.027(3) -0.008(4) C20 0.043(4) 0.028(4) 0.038(3) -0.004(3) 0.018(3) 0.000(3) C21 0.050(4) 0.033(4) 0.048(4) 0.006(3) 0.026(3) -0.001(3) C22 0.045(4) 0.043(5) 0.055(4) 0.001(4) 0.029(3) -0.007(3) C23 0.034(3) 0.047(4) 0.047(4) -0.001(3) 0.023(3) 0.008(3) C24 0.037(3) 0.033(4) 0.045(4) 0.001(3) 0.014(3) 0.003(3) C25 0.036(3) 0.047(4) 0.049(4) -0.013(3) 0.025(3) -0.008(3) C26 0.043(4) 0.038(4) 0.055(4) -0.009(3) 0.035(3) 0.000(3) C27 0.049(4) 0.039(4) 0.048(4) -0.006(3) 0.030(3) -0.007(3) C28 0.044(4) 0.044(4) 0.065(4) -0.011(4) 0.035(4) -0.009(3) C29 0.040(4) 0.043(4) 0.055(4) -0.007(3) 0.032(3) -0.004(3) C30 0.043(4) 0.042(5) 0.062(5) 0.006(4) 0.031(4) 0.004(3) C31 0.056(4) 0.040(4) 0.079(5) 0.013(4) 0.036(4) -0.002(4) C32 0.044(4) 0.058(6) 0.069(5) 0.019(4) 0.029(4) -0.002(4) C33 0.036(4) 0.071(6) 0.062(5) 0.010(4) 0.025(3) 0.006(4) C34 0.039(4) 0.040(4) 0.041(4) 0.000(3) 0.016(3) 0.002(3) C35 0.053(4) 0.044(5) 0.044(4) 0.006(4) 0.023(3) 0.002(3) C36 0.067(5) 0.042(5) 0.046(4) -0.016(4) 0.020(4) -0.003(4) C37 0.064(6) 0.024(5) 0.049(6) 0.000 0.025(5) 0.000 _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 O2 1.888(11) . ? Li1 O1 1.893(10) . ? Li1 N3 2.079(11) . ? Li1 N4 2.091(11) . ? Li1 Li2 2.649(12) . ? Li2 O1 1.893(10) . ? Li2 O2 1.933(10) . ? Li2 N5 2.068(11) . ? Li2 N6 2.079(11) . ? O1 C1 1.305(6) . ? O2 C8 1.304(6) . ? N1 C7 1.139(7) . ? N2 C14 1.142(7) . ? N3 C15 1.315(7) . ? N3 C19 1.337(8) . ? N4 C20 1.341(8) . ? N4 C24 1.341(7) . ? N5 C25 1.335(8) . ? N5 C29 1.351(7) . ? N6 C34 1.337(7) . ? N6 C30 1.341(9) . ? N7 C35 1.330(7) . ? N7 C35 1.330(7) 2 ? C1 C2 1.409(7) . ? C1 C6 1.425(7) . ? C2 C3 1.364(7) . ? C2 H2 0.9500 . ? C3 C4 1.413(7) . ? C3 H3 0.9500 . ? C4 C5 1.395(8) . ? C4 C7 1.449(8) . ? C5 C6 1.372(7) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C8 C9 1.398(7) . ? C8 C13 1.421(7) . ? C9 C10 1.387(7) . ? C9 H9 0.9500 . ? C10 C11 1.390(7) . ? C10 H10 0.9500 . ? C11 C12 1.390(8) . ? C11 C14 1.449(8) . ? C12 C13 1.390(7) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C15 C16 1.372(8) . ? C15 H15 0.9500 . ? C16 C17 1.370(9) . ? C16 H16 0.9500 . ? C17 C18 1.363(8) . ? C17 H17 0.9500 . ? C18 C19 1.393(9) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C21 1.366(9) . ? C20 H20 0.9500 . ? C21 C22 1.386(9) . ? C21 H21 0.9500 . ? C22 C23 1.378(9) . ? C22 H22 0.9500 . ? C23 C24 1.382(9) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C26 1.377(9) . ? C25 H25 0.9500 . ? C26 C27 1.368(8) . ? C26 H26 0.9500 . ? C27 C28 1.370(9) . ? C27 H27 0.9500 . ? C28 C29 1.372(9) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 C31 1.375(9) . ? C30 H30 0.9500 . ? C31 C32 1.376(9) . ? C31 H31 0.9500 . ? C32 C33 1.377(10) . ? C32 H32 0.9500 . ? C33 C34 1.379(9) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? C35 C36 1.369(9) . ? C35 H35 0.9500 . ? C36 C37 1.349(8) . ? C36 H36 0.9500 . ? C37 C36 1.349(8) 2 ? C37 H37 0.9500 . ? N8 C40 1.348(11) . ? N8 C40 1.348(11) 2_656 ? C40 C39 1.401(14) . ? C40 H40 0.9500 . ? C39 C38 1.291(13) . ? C39 H39 0.9500 . ? C38 C39 1.291(13) 2_656 ? C38 H38 0.9500 . ? 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 O2 Li1 O1 92.4(5) . . ? O2 Li1 N3 115.4(5) . . ? O1 Li1 N3 110.5(5) . . ? O2 Li1 N4 109.0(5) . . ? O1 Li1 N4 119.5(5) . . ? N3 Li1 N4 109.4(5) . . ? O2 Li1 Li2 46.8(3) . . ? O1 Li1 Li2 45.6(3) . . ? N3 Li1 Li2 123.8(5) . . ? N4 Li1 Li2 126.8(5) . . ? O1 Li2 O2 91.0(4) . . ? O1 Li2 N5 107.9(5) . . ? O2 Li2 N5 114.8(5) . . ? O1 Li2 N6 115.2(5) . . ? O2 Li2 N6 109.9(5) . . ? N5 Li2 N6 115.6(5) . . ? O1 Li2 Li1 45.6(3) . . ? O2 Li2 Li1 45.4(3) . . ? N5 Li2 Li1 121.7(5) . . ? N6 Li2 Li1 122.8(5) . . ? C1 O1 Li2 142.5(4) . . ? C1 O1 Li1 128.3(4) . . ? Li2 O1 Li1 88.8(4) . . ? C8 O2 Li1 141.8(5) . . ? C8 O2 Li2 129.6(5) . . ? Li1 O2 Li2 87.8(4) . . ? C15 N3 C19 116.4(5) . . ? C15 N3 Li1 128.2(5) . . ? C19 N3 Li1 114.2(5) . . ? C20 N4 C24 116.1(6) . . ? C20 N4 Li1 114.4(6) . . ? C24 N4 Li1 129.4(5) . . ? C25 N5 C29 116.0(5) . . ? C25 N5 Li2 133.0(5) . . ? C29 N5 Li2 111.0(5) . . ? C34 N6 C30 116.0(6) . . ? C34 N6 Li2 128.6(5) . . ? C30 N6 Li2 115.0(5) . . ? C35 N7 C35 116.0(8) . 2 ? O1 C1 C2 121.4(5) . . ? O1 C1 C6 122.3(5) . . ? C2 C1 C6 116.3(5) . . ? C3 C2 C1 122.6(5) . . ? C3 C2 H2 118.7 . . ? C1 C2 H2 118.7 . . ? C2 C3 C4 119.8(6) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 119.1(5) . . ? C5 C4 C7 120.8(5) . . ? C3 C4 C7 120.0(5) . . ? C6 C5 C4 120.4(5) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 121.7(6) . . ? C5 C6 H6 119.2 . . ? C1 C6 H6 119.2 . . ? N1 C7 C4 178.8(7) . . ? O2 C8 C9 122.1(5) . . ? O2 C8 C13 121.3(5) . . ? C9 C8 C13 116.6(5) . . ? C10 C9 C8 122.0(5) . . ? C10 C9 H9 119.0 . . ? C8 C9 H9 119.0 . . ? C9 C10 C11 120.2(5) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C10 119.8(5) . . ? C12 C11 C14 120.8(5) . . ? C10 C11 C14 119.3(5) . . ? C13 C12 C11 119.7(5) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C8 121.7(5) . . ? C12 C13 H13 119.2 . . ? C8 C13 H13 119.2 . . ? N2 C14 C11 179.2(7) . . ? N3 C15 C16 125.1(6) . . ? N3 C15 H15 117.4 . . ? C16 C15 H15 117.4 . . ? C17 C16 C15 117.5(6) . . ? C17 C16 H16 121.2 . . ? C15 C16 H16 121.2 . . ? C18 C17 C16 119.7(6) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C17 C18 C19 118.2(6) . . ? C17 C18 H18 120.9 . . ? C19 C18 H18 120.9 . . ? N3 C19 C18 122.9(6) . . ? N3 C19 H19 118.5 . . ? C18 C19 H19 118.5 . . ? N4 C20 C21 124.3(7) . . ? N4 C20 H20 117.8 . . ? C21 C20 H20 117.8 . . ? C20 C21 C22 119.3(6) . . ? C20 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? C23 C22 C21 117.3(6) . . ? C23 C22 H22 121.3 . . ? C21 C22 H22 121.3 . . ? C22 C23 C24 119.9(6) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? N4 C24 C23 123.1(6) . . ? N4 C24 H24 118.4 . . ? C23 C24 H24 118.4 . . ? N5 C25 C26 123.3(6) . . ? N5 C25 H25 118.3 . . ? C26 C25 H25 118.3 . . ? C27 C26 C25 119.5(6) . . ? C27 C26 H26 120.2 . . ? C25 C26 H26 120.2 . . ? C26 C27 C28 118.5(6) . . ? C26 C27 H27 120.7 . . ? C28 C27 H27 120.7 . . ? C27 C28 C29 118.7(6) . . ? C27 C28 H28 120.7 . . ? C29 C28 H28 120.7 . . ? N5 C29 C28 124.0(6) . . ? N5 C29 H29 118.0 . . ? C28 C29 H29 118.0 . . ? N6 C30 C31 124.2(6) . . ? N6 C30 H30 117.9 . . ? C31 C30 H30 117.9 . . ? C30 C31 C32 118.5(7) . . ? C30 C31 H31 120.8 . . ? C32 C31 H31 120.8 . . ? C31 C32 C33 118.7(7) . . ? C31 C32 H32 120.7 . . ? C33 C32 H32 120.7 . . ? C32 C33 C34 118.8(7) . . ? C32 C33 H33 120.6 . . ? C34 C33 H33 120.6 . . ? N6 C34 C33 123.8(7) . . ? N6 C34 H34 118.1 . . ? C33 C34 H34 118.1 . . ? N7 C35 C36 123.8(7) . . ? N7 C35 H35 118.1 . . ? C36 C35 H35 118.1 . . ? C37 C36 C35 118.1(7) . . ? C37 C36 H36 121.0 . . ? C35 C36 H36 121.0 . . ? C36 C37 C36 120.3(9) 2 . ? C36 C37 H37 119.9 2 . ? C36 C37 H37 119.9 . . ? C40 N8 C40 115.4(13) . 2_656 ? N8 C40 C39 122.9(12) . . ? N8 C40 H40 118.5 . . ? C39 C40 H40 118.5 . . ? C38 C39 C40 115.4(15) . . ? C38 C39 H39 122.3 . . ? C40 C39 H39 122.3 . . ? C39 C38 C39 128(2) 2_656 . ? C39 C38 H38 116.2 2_656 . ? C39 C38 H38 116.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Li1 Li2 O1 179.2(7) . . . . ? N3 Li1 Li2 O1 -86.2(6) . . . . ? N4 Li1 Li2 O1 97.4(6) . . . . ? O1 Li1 Li2 O2 -179.2(7) . . . . ? N3 Li1 Li2 O2 94.6(6) . . . . ? N4 Li1 Li2 O2 -81.7(6) . . . . ? O2 Li1 Li2 N5 94.9(6) . . . . ? O1 Li1 Li2 N5 -84.3(5) . . . . ? N3 Li1 Li2 N5 -170.5(5) . . . . ? N4 Li1 Li2 N5 13.2(8) . . . . ? O2 Li1 Li2 N6 -86.3(5) . . . . ? O1 Li1 Li2 N6 94.6(6) . . . . ? N3 Li1 Li2 N6 8.3(8) . . . . ? N4 Li1 Li2 N6 -168.0(5) . . . . ? O2 Li2 O1 C1 -171.9(6) . . . . ? N5 Li2 O1 C1 -55.4(9) . . . . ? N6 Li2 O1 C1 75.4(9) . . . . ? Li1 Li2 O1 C1 -172.5(9) . . . . ? O2 Li2 O1 Li1 0.6(5) . . . . ? N5 Li2 O1 Li1 117.2(5) . . . . ? N6 Li2 O1 Li1 -112.1(5) . . . . ? O2 Li1 O1 C1 173.6(4) . . . . ? N3 Li1 O1 C1 -68.1(7) . . . . ? N4 Li1 O1 C1 60.1(8) . . . . ? Li2 Li1 O1 C1 174.2(7) . . . . ? O2 Li1 O1 Li2 -0.6(5) . . . . ? N3 Li1 O1 Li2 117.7(5) . . . . ? N4 Li1 O1 Li2 -114.1(6) . . . . ? O1 Li1 O2 C8 170.0(6) . . . . ? N3 Li1 O2 C8 55.9(10) . . . . ? N4 Li1 O2 C8 -67.6(8) . . . . ? Li2 Li1 O2 C8 169.4(8) . . . . ? O1 Li1 O2 Li2 0.6(5) . . . . ? N3 Li1 O2 Li2 -113.4(5) . . . . ? N4 Li1 O2 Li2 123.0(5) . . . . ? O1 Li2 O2 C8 -172.1(4) . . . . ? N5 Li2 O2 C8 77.7(7) . . . . ? N6 Li2 O2 C8 -54.7(8) . . . . ? Li1 Li2 O2 C8 -171.5(7) . . . . ? O1 Li2 O2 Li1 -0.6(5) . . . . ? N5 Li2 O2 Li1 -110.8(5) . . . . ? N6 Li2 O2 Li1 116.8(5) . . . . ? O2 Li1 N3 C15 -84.2(8) . . . . ? O1 Li1 N3 C15 172.8(5) . . . . ? N4 Li1 N3 C15 39.2(8) . . . . ? Li2 Li1 N3 C15 -137.7(6) . . . . ? O2 Li1 N3 C19 82.2(7) . . . . ? O1 Li1 N3 C19 -20.9(7) . . . . ? N4 Li1 N3 C19 -154.5(5) . . . . ? Li2 Li1 N3 C19 28.6(7) . . . . ? O2 Li1 N4 C20 -22.6(7) . . . . ? O1 Li1 N4 C20 81.7(7) . . . . ? N3 Li1 N4 C20 -149.6(5) . . . . ? Li2 Li1 N4 C20 27.2(7) . . . . ? O2 Li1 N4 C24 152.8(5) . . . . ? O1 Li1 N4 C24 -103.0(7) . . . . ? N3 Li1 N4 C24 25.7(7) . . . . ? Li2 Li1 N4 C24 -157.5(5) . . . . ? O1 Li2 N5 C25 152.3(6) . . . . ? O2 Li2 N5 C25 -107.9(7) . . . . ? N6 Li2 N5 C25 21.7(9) . . . . ? Li1 Li2 N5 C25 -159.4(6) . . . . ? O1 Li2 N5 C29 -28.8(6) . . . . ? O2 Li2 N5 C29 71.0(6) . . . . ? N6 Li2 N5 C29 -159.4(5) . . . . ? Li1 Li2 N5 C29 19.5(6) . . . . ? O1 Li2 N6 C34 -179.7(5) . . . . ? O2 Li2 N6 C34 79.3(7) . . . . ? N5 Li2 N6 C34 -52.7(8) . . . . ? Li1 Li2 N6 C34 128.4(6) . . . . ? O1 Li2 N6 C30 8.2(7) . . . . ? O2 Li2 N6 C30 -92.8(6) . . . . ? N5 Li2 N6 C30 135.2(6) . . . . ? Li1 Li2 N6 C30 -43.7(7) . . . . ? Li2 O1 C1 C2 -166.0(7) . . . . ? Li1 O1 C1 C2 23.5(8) . . . . ? Li2 O1 C1 C6 14.2(11) . . . . ? Li1 O1 C1 C6 -156.2(6) . . . . ? O1 C1 C2 C3 178.5(5) . . . . ? C6 C1 C2 C3 -1.8(8) . . . . ? C1 C2 C3 C4 1.8(9) . . . . ? C2 C3 C4 C5 -0.3(8) . . . . ? C2 C3 C4 C7 178.1(5) . . . . ? C3 C4 C5 C6 -1.1(8) . . . . ? C7 C4 C5 C6 -179.4(6) . . . . ? C4 C5 C6 C1 1.0(9) . . . . ? O1 C1 C6 C5 -179.9(5) . . . . ? C2 C1 C6 C5 0.4(9) . . . . ? C5 C4 C7 N1 -168(100) . . . . ? C3 C4 C7 N1 13(33) . . . . ? Li1 O2 C8 C9 173.6(6) . . . . ? Li2 O2 C8 C9 -20.2(8) . . . . ? Li1 O2 C8 C13 -4.3(10) . . . . ? Li2 O2 C8 C13 161.9(6) . . . . ? O2 C8 C9 C10 -178.5(5) . . . . ? C13 C8 C9 C10 -0.5(8) . . . . ? C8 C9 C10 C11 -0.7(9) . . . . ? C9 C10 C11 C12 1.4(9) . . . . ? C9 C10 C11 C14 -177.4(6) . . . . ? C10 C11 C12 C13 -0.9(9) . . . . ? C14 C11 C12 C13 177.9(6) . . . . ? C11 C12 C13 C8 -0.3(9) . . . . ? O2 C8 C13 C12 179.0(5) . . . . ? C9 C8 C13 C12 1.0(8) . . . . ? C12 C11 C14 N2 -178(100) . . . . ? C10 C11 C14 N2 1(60) . . . . ? C19 N3 C15 C16 -3.6(9) . . . . ? Li1 N3 C15 C16 162.5(6) . . . . ? N3 C15 C16 C17 0.0(9) . . . . ? C15 C16 C17 C18 3.5(9) . . . . ? C16 C17 C18 C19 -3.3(10) . . . . ? C15 N3 C19 C18 3.8(9) . . . . ? Li1 N3 C19 C18 -164.2(6) . . . . ? C17 C18 C19 N3 -0.5(10) . . . . ? C24 N4 C20 C21 -0.9(9) . . . . ? Li1 N4 C20 C21 175.1(5) . . . . ? N4 C20 C21 C22 -0.6(9) . . . . ? C20 C21 C22 C23 1.5(9) . . . . ? C21 C22 C23 C24 -1.1(9) . . . . ? C20 N4 C24 C23 1.3(8) . . . . ? Li1 N4 C24 C23 -173.9(5) . . . . ? C22 C23 C24 N4 -0.3(9) . . . . ? C29 N5 C25 C26 -1.1(9) . . . . ? Li2 N5 C25 C26 177.7(6) . . . . ? N5 C25 C26 C27 -0.9(10) . . . . ? C25 C26 C27 C28 2.2(9) . . . . ? C26 C27 C28 C29 -1.5(10) . . . . ? C25 N5 C29 C28 1.9(9) . . . . ? Li2 N5 C29 C28 -177.3(6) . . . . ? C27 C28 C29 N5 -0.6(10) . . . . ? C34 N6 C30 C31 -1.0(10) . . . . ? Li2 N6 C30 C31 172.1(6) . . . . ? N6 C30 C31 C32 2.2(11) . . . . ? C30 C31 C32 C33 -2.0(11) . . . . ? C31 C32 C33 C34 0.8(12) . . . . ? C30 N6 C34 C33 -0.3(9) . . . . ? Li2 N6 C34 C33 -172.4(6) . . . . ? C32 C33 C34 N6 0.5(11) . . . . ? C35 N7 C35 C36 0.5(6) 2 . . . ? N7 C35 C36 C37 -1.1(11) . . . . ? C35 C36 C37 C36 0.5(5) . . . 2 ? C40 N8 C40 C39 -3.0(8) 2_656 . . . ? N8 C40 C39 C38 5.9(16) . . . . ? C40 C39 C38 C39 -2.8(7) . . . 2_656 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.95 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.519 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.048 # Attachment '1b.cif' data_kwh202a _database_code_depnum_ccdc_archive 'CCDC 287369' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'Lithium 4-cyanophenoxide THF solvate' _chemical_melting_point ? _chemical_formula_moiety '2(C30 H40 Li2 N2 O6)' _chemical_formula_sum 'C60 H80 Li4 N4 O12' _chemical_formula_weight 1077.04 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_int_tables_number 29 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 19.0800(9) _cell_length_b 19.4540(9) _cell_length_c 16.0843(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5970.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9813 _cell_measurement_theta_min 2.482 _cell_measurement_theta_max 28.2545 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.198 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2304 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9451 _exptl_absorpt_correction_T_max 0.9604 _exptl_absorpt_process_details 'Blessing, R. H. (1995) Acta Cryst. A51, 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Siemens KFFMO2K-90' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 61781 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 28.30 _reflns_number_total 14821 _reflns_number_gt 12981 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART/SAINT (Bruker, 2001)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2001; Sheldrick, 2003)' _computing_structure_solution 'XS (Sheldrick, 2001)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Sheldrick, 1998)' _computing_publication_material 'XCIF (Sheldrick, 2001)' _refine_special_details ; This light atom molecule was solved as a racemic twin with a Flack parameter of 0.57(18). There are two dimeric molecules per ASU. Disorder was observed in the positions of THF ring O4, C19-C22. Alternate positions were modelled for C21. Site occupancy for the major component was refined to 0.702(13). Disorder was observed in the positions of THF ring O5, C23-C26. Alternate positions were modelled for C23 and C25. Site occupancy for the major component was refined to 0.507(9) and 0.56(2) respectively. All hydrogen atoms were placed in calculated positions and allowed to ride on the position of the parent atom. Hydrogen thermal parameters were set to 1.2\\times the equivalent isotropic U of the parent atom. All non-hydrogen atoms were modeled with parameters for anisotropic thermal motion. 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^)+(0.0742P)^2^+0.8961P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.57(18) _refine_ls_number_reflns 14821 _refine_ls_number_parameters 752 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1244 _refine_ls_wR_factor_gt 0.1178 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 Li1 Li 0.23296(15) 0.05051(14) 0.28659(19) 0.0303(6) Uani 1 1 d . . . Li2 Li 0.30019(15) 0.15637(15) 0.35560(19) 0.0298(6) Uani 1 1 d . C . Li3 Li 0.70369(15) 0.32381(14) 0.7855(2) 0.0312(6) Uani 1 1 d . . . Li4 Li 0.76791(14) 0.43286(15) 0.8506(2) 0.0302(6) Uani 1 1 d . . . N1 N 0.50626(10) -0.16982(10) 0.56203(14) 0.0532(5) Uani 1 1 d . . . N2 N 0.04529(8) 0.37239(8) 0.04495(10) 0.0358(3) Uani 1 1 d . . . N3 N 0.50751(9) 0.64217(8) 0.54274(11) 0.0423(4) Uani 1 1 d . . . N4 N 0.96417(8) 0.11170(8) 1.08831(10) 0.0352(3) Uani 1 1 d . . . O1 O 0.29456(6) 0.06041(6) 0.37879(7) 0.0277(2) Uani 1 1 d . . . O2 O 0.23512(6) 0.14659(6) 0.26573(9) 0.0338(3) Uani 1 1 d . . . O3 O 0.13951(6) 0.01226(6) 0.30538(9) 0.0354(3) Uani 1 1 d . . . O4 O 0.27619(6) -0.00545(7) 0.19804(8) 0.0312(3) Uani 1 1 d . B . O5 O 0.26443(9) 0.21947(7) 0.43880(12) 0.0572(5) Uani 1 1 d . . . O6 O 0.39010(6) 0.19666(7) 0.32432(8) 0.0374(3) Uani 1 1 d . . . O7 O 0.70064(6) 0.42022(6) 0.76543(7) 0.0285(2) Uani 1 1 d . . . O8 O 0.77010(6) 0.33758(6) 0.87291(8) 0.0320(3) Uani 1 1 d . . . O9 O 0.62041(6) 0.27154(6) 0.81672(8) 0.0348(3) Uani 1 1 d . . . O10 O 0.73886(8) 0.27388(6) 0.68859(10) 0.0432(3) Uani 1 1 d . . . O11 O 0.72995(6) 0.49515(6) 0.93682(8) 0.0312(3) Uani 1 1 d . . . O12 O 0.86127(6) 0.46931(7) 0.82377(10) 0.0402(3) Uani 1 1 d . . . C1 C 0.46834(9) -0.13130(10) 0.53196(13) 0.0363(4) Uani 1 1 d . . . C2 C 0.42192(8) -0.08229(8) 0.49427(11) 0.0273(3) Uani 1 1 d . . . C3 C 0.43077(8) -0.01207(8) 0.50981(11) 0.0272(3) Uani 1 1 d . . . H3 H 0.4664 0.0028 0.5469 0.033 Uiso 1 1 calc R . . C4 C 0.38814(8) 0.03577(8) 0.47171(10) 0.0260(3) Uani 1 1 d . . . H4 H 0.3949 0.0832 0.4830 0.031 Uiso 1 1 calc R . . C5 C 0.33411(8) 0.01543(8) 0.41577(9) 0.0229(3) Uani 1 1 d . . . C6 C 0.32556(8) -0.05611(8) 0.40242(10) 0.0256(3) Uani 1 1 d . . . H6 H 0.2894 -0.0716 0.3663 0.031 Uiso 1 1 calc R . . C7 C 0.36838(8) -0.10386(8) 0.44054(10) 0.0266(3) Uani 1 1 d . . . H7 H 0.3616 -0.1515 0.4303 0.032 Uiso 1 1 calc R . . C8 C 0.07733(8) 0.33502(8) 0.08523(11) 0.0284(3) Uani 1 1 d . . . C9 C 0.11736(8) 0.28725(8) 0.13285(10) 0.0263(3) Uani 1 1 d . . . C10 C 0.16716(9) 0.30919(8) 0.19064(11) 0.0300(3) Uani 1 1 d . . . H10 H 0.1738 0.3570 0.1999 0.036 Uiso 1 1 calc R . . C11 C 0.20685(9) 0.26221(9) 0.23443(11) 0.0308(3) Uani 1 1 d . . . H11 H 0.2408 0.2785 0.2729 0.037 Uiso 1 1 calc R . . C12 C 0.19839(8) 0.19036(9) 0.22371(11) 0.0281(3) Uani 1 1 d . . . C13 C 0.14685(9) 0.16929(9) 0.16535(11) 0.0314(4) Uani 1 1 d . . . H13 H 0.1390 0.1216 0.1567 0.038 Uiso 1 1 calc R . . C14 C 0.10790(9) 0.21617(8) 0.12091(11) 0.0285(3) Uani 1 1 d . . . H14 H 0.0743 0.2004 0.0818 0.034 Uiso 1 1 calc R . . C15 C 0.10788(10) -0.04650(10) 0.26477(15) 0.0410(4) Uani 1 1 d . . . H15A H 0.1271 -0.0898 0.2876 0.049 Uiso 1 1 calc R . . H15B H 0.1171 -0.0453 0.2042 0.049 Uiso 1 1 calc R . . C16 C 0.03016(10) -0.04161(11) 0.28168(16) 0.0456(5) Uani 1 1 d . . . H16A H 0.0170 -0.0688 0.3313 0.055 Uiso 1 1 calc R . . H16B H 0.0026 -0.0579 0.2334 0.055 Uiso 1 1 calc R . . C17 C 0.01880(9) 0.03535(9) 0.29662(12) 0.0338(4) Uani 1 1 d . . . H17A H 0.0142 0.0609 0.2436 0.041 Uiso 1 1 calc R . . H17B H -0.0231 0.0439 0.3314 0.041 Uiso 1 1 calc R . . C18 C 0.08562(9) 0.05425(10) 0.34197(13) 0.0363(4) Uani 1 1 d . . . H18A H 0.0964 0.1036 0.3345 0.044 Uiso 1 1 calc R . . H18B H 0.0812 0.0445 0.4022 0.044 Uiso 1 1 calc R . . C19 C 0.35119(9) 0.00541(11) 0.19343(12) 0.0368(4) Uani 1 1 d . B . H19A H 0.3765 -0.0388 0.1982 0.044 Uiso 1 1 calc R . . H19B H 0.3670 0.0362 0.2387 0.044 Uiso 1 1 calc R . . C20 C 0.36454(10) 0.03801(12) 0.10965(13) 0.0422(4) Uani 1 1 d . . . H20A H 0.3570 0.0883 0.1114 0.051 Uiso 1 1 calc R A 1 H20B H 0.4127 0.0284 0.0897 0.051 Uiso 1 1 calc R A 1 C21 C 0.31070(18) 0.0029(2) 0.05668(17) 0.0308(9) Uani 0.703(13) 1 d P B 1 H21A H 0.3275 -0.0426 0.0378 0.037 Uiso 0.703(13) 1 calc PR B 1 H21B H 0.2987 0.0312 0.0075 0.037 Uiso 0.703(13) 1 calc PR B 1 C21A C 0.2904(6) 0.0377(9) 0.0645(6) 0.052(4) Uani 0.297(13) 1 d P B 2 H21C H 0.2709 0.0848 0.0613 0.063 Uiso 0.297(13) 1 calc PR B 2 H21D H 0.2944 0.0189 0.0075 0.063 Uiso 0.297(13) 1 calc PR B 2 C22 C 0.24858(11) -0.00430(12) 0.11408(12) 0.0433(5) Uani 1 1 d . . . H22A H 0.2161 0.0349 0.1069 0.052 Uiso 1 1 calc R B 1 H22B H 0.2229 -0.0474 0.1021 0.052 Uiso 1 1 calc R B 1 C23 C 0.2135(2) 0.1928(2) 0.4984(3) 0.0351(13) Uani 0.494(9) 1 d P C 1 H23A H 0.2374 0.1688 0.5447 0.042 Uiso 0.494(9) 1 calc PR C 1 H23B H 0.1807 0.1604 0.4711 0.042 Uiso 0.494(9) 1 calc PR C 1 C23A C 0.1860(3) 0.2053(2) 0.4558(4) 0.0434(15) Uani 0.506(9) 1 d P C 2 H23C H 0.1562 0.2174 0.4076 0.052 Uiso 0.506(9) 1 calc PR C 2 H23D H 0.1775 0.1568 0.4718 0.052 Uiso 0.506(9) 1 calc PR C 2 C24 C 0.17531(13) 0.25490(13) 0.52936(15) 0.0513(5) Uani 1 1 d . . . H24A H 0.1902 0.2667 0.5866 0.062 Uiso 1 1 calc R C 1 H24B H 0.1240 0.2472 0.5289 0.062 Uiso 1 1 calc R C 1 C25 C 0.1959(5) 0.3116(4) 0.4682(6) 0.0471(17) Uani 0.56(2) 1 d P C 1 H25A H 0.1664 0.3105 0.4176 0.057 Uiso 0.56(2) 1 calc PR C 1 H25B H 0.1928 0.3577 0.4941 0.057 Uiso 0.56(2) 1 calc PR C 1 C25A C 0.2115(5) 0.3184(4) 0.4987(10) 0.044(2) Uani 0.44(2) 1 d P C 2 H25C H 0.1798 0.3463 0.4635 0.053 Uiso 0.44(2) 1 calc PR C 2 H25D H 0.2281 0.3469 0.5458 0.053 Uiso 0.44(2) 1 calc PR C 2 C26 C 0.27166(10) 0.29183(9) 0.44940(12) 0.0365(4) Uani 1 1 d . C . H26A H 0.2890 0.3143 0.3981 0.044 Uiso 1 1 calc R D 1 H26B H 0.3032 0.3031 0.4963 0.044 Uiso 1 1 calc R D 1 C27 C 0.44878(10) 0.21503(12) 0.37743(12) 0.0431(4) Uani 1 1 d . C . H27A H 0.4630 0.1755 0.4122 0.052 Uiso 1 1 calc R . . H27B H 0.4362 0.2539 0.4143 0.052 Uiso 1 1 calc R . . C28 C 0.50772(10) 0.23548(11) 0.31843(14) 0.0437(4) Uani 1 1 d . . . H28A H 0.5383 0.2710 0.3436 0.052 Uiso 1 1 calc R C . H28B H 0.5366 0.1952 0.3029 0.052 Uiso 1 1 calc R . . C29 C 0.46920(11) 0.26329(11) 0.24492(13) 0.0424(4) Uani 1 1 d . C . H29A H 0.4980 0.2607 0.1938 0.051 Uiso 1 1 calc R . . H29B H 0.4545 0.3115 0.2541 0.051 Uiso 1 1 calc R . . C30 C 0.40659(10) 0.21551(11) 0.24018(11) 0.0367(4) Uani 1 1 d . C . H30A H 0.3663 0.2391 0.2140 0.044 Uiso 1 1 calc R . . H30B H 0.4181 0.1742 0.2070 0.044 Uiso 1 1 calc R . . C31 C 0.54188(9) 0.60525(9) 0.58079(12) 0.0320(3) Uani 1 1 d . . . C32 C 0.58352(8) 0.55798(8) 0.62787(10) 0.0261(3) Uani 1 1 d . . . C33 C 0.63835(8) 0.58096(8) 0.67884(10) 0.0267(3) Uani 1 1 d . . . H33 H 0.6486 0.6287 0.6818 0.032 Uiso 1 1 calc R . . C34 C 0.67735(8) 0.53517(8) 0.72448(10) 0.0255(3) Uani 1 1 d . . . H34 H 0.7142 0.5519 0.7586 0.031 Uiso 1 1 calc R . . C35 C 0.66398(8) 0.46323(8) 0.72193(10) 0.0252(3) Uani 1 1 d . . . C36 C 0.60836(8) 0.44117(8) 0.66999(10) 0.0270(3) Uani 1 1 d . . . H36 H 0.5979 0.3935 0.6664 0.032 Uiso 1 1 calc R . . C37 C 0.56909(8) 0.48728(8) 0.62456(11) 0.0274(3) Uani 1 1 d . . . H37 H 0.5318 0.4710 0.5906 0.033 Uiso 1 1 calc R . . C38 C 0.93047(8) 0.14935(8) 1.05049(11) 0.0285(3) Uani 1 1 d . . . C39 C 0.88884(8) 0.19726(8) 1.00450(10) 0.0260(3) Uani 1 1 d . . . C40 C 0.83619(9) 0.17514(8) 0.94982(11) 0.0308(3) Uani 1 1 d . . . H40 H 0.8279 0.1274 0.9428 0.037 Uiso 1 1 calc R . . C41 C 0.79651(9) 0.22198(9) 0.90632(11) 0.0312(4) Uani 1 1 d . . . H41 H 0.7610 0.2058 0.8698 0.037 Uiso 1 1 calc R . . C42 C 0.80739(8) 0.29390(8) 0.91463(10) 0.0262(3) Uani 1 1 d . . . C43 C 0.86071(8) 0.31501(8) 0.97068(11) 0.0270(3) Uani 1 1 d . . . H43 H 0.8694 0.3627 0.9781 0.032 Uiso 1 1 calc R . . C44 C 0.90002(8) 0.26822(8) 1.01437(10) 0.0266(3) Uani 1 1 d . . . H44 H 0.9351 0.2840 1.0517 0.032 Uiso 1 1 calc R . . C45 C 0.57942(11) 0.22527(11) 0.76565(12) 0.0424(4) Uani 1 1 d . . . H45A H 0.6020 0.1795 0.7626 0.051 Uiso 1 1 calc R . . H45B H 0.5746 0.2437 0.7086 0.051 Uiso 1 1 calc R . . C46 C 0.50884(11) 0.22016(11) 0.80717(14) 0.0448(5) Uani 1 1 d . . . H46A H 0.5086 0.1839 0.8504 0.054 Uiso 1 1 calc R . . H46B H 0.4714 0.2104 0.7662 0.054 Uiso 1 1 calc R . . C47 C 0.49989(11) 0.29065(14) 0.84516(17) 0.0553(6) Uani 1 1 d . . . H47A H 0.4661 0.2899 0.8918 0.066 Uiso 1 1 calc R . . H47B H 0.4844 0.3248 0.8033 0.066 Uiso 1 1 calc R . . C48 C 0.57453(10) 0.30544(11) 0.87546(14) 0.0423(5) Uani 1 1 d . . . H48A H 0.5836 0.3555 0.8763 0.051 Uiso 1 1 calc R . . H48B H 0.5817 0.2869 0.9322 0.051 Uiso 1 1 calc R . . C49 C 0.78553(12) 0.31314(11) 0.63611(15) 0.0479(5) Uani 1 1 d . . . H49A H 0.8127 0.3463 0.6699 0.057 Uiso 1 1 calc R . . H49B H 0.7584 0.3391 0.5941 0.057 Uiso 1 1 calc R . . C50 C 0.83399(11) 0.26307(11) 0.59420(14) 0.0439(4) Uani 1 1 d . . . H50A H 0.8829 0.2801 0.5944 0.053 Uiso 1 1 calc R . . H50B H 0.8193 0.2542 0.5361 0.053 Uiso 1 1 calc R . . C51 C 0.82654(12) 0.19893(11) 0.64739(17) 0.0512(5) Uani 1 1 d . . . H51A H 0.8363 0.1568 0.6148 0.061 Uiso 1 1 calc R . . H51B H 0.8582 0.2005 0.6961 0.061 Uiso 1 1 calc R . . C52 C 0.75032(10) 0.20234(9) 0.67360(12) 0.0354(4) Uani 1 1 d . . . H52A H 0.7192 0.1852 0.6289 0.043 Uiso 1 1 calc R . . H52B H 0.7421 0.1750 0.7246 0.043 Uiso 1 1 calc R . . C53 C 0.65437(9) 0.50268(9) 0.93981(12) 0.0324(4) Uani 1 1 d . . . H53A H 0.6319 0.4757 0.8949 0.039 Uiso 1 1 calc R . . H53B H 0.6409 0.5515 0.9336 0.039 Uiso 1 1 calc R . . C54 C 0.63268(9) 0.47587(10) 1.02372(12) 0.0340(4) Uani 1 1 d . . . H54A H 0.6282 0.4252 1.0235 0.041 Uiso 1 1 calc R . . H54B H 0.5879 0.4965 1.0422 0.041 Uiso 1 1 calc R . . C55 C 0.69360(9) 0.49919(9) 1.07810(12) 0.0341(4) Uani 1 1 d . . . H55A H 0.6892 0.5483 1.0934 0.041 Uiso 1 1 calc R . . H55B H 0.6971 0.4712 1.1293 0.041 Uiso 1 1 calc R . . C56 C 0.75577(10) 0.48710(10) 1.02093(12) 0.0349(4) Uani 1 1 d . . . H56A H 0.7933 0.5209 1.0324 0.042 Uiso 1 1 calc R . . H56B H 0.7749 0.4403 1.0291 0.042 Uiso 1 1 calc R . . C57 C 0.89255(11) 0.53077(11) 0.8578(2) 0.0613(7) Uani 1 1 d . . . H57A H 0.8775 0.5372 0.9162 0.074 Uiso 1 1 calc R . . H57B H 0.8777 0.5715 0.8253 0.074 Uiso 1 1 calc R . . C58 C 0.96870(13) 0.52284(16) 0.8536(2) 0.0756(9) Uani 1 1 d . . . H58A H 0.9905 0.5367 0.9069 0.091 Uiso 1 1 calc R . . H58B H 0.9884 0.5516 0.8086 0.091 Uiso 1 1 calc R . . C59 C 0.98217(9) 0.44778(11) 0.83654(13) 0.0401(4) Uani 1 1 d . . . H59A H 0.9878 0.4215 0.8888 0.048 Uiso 1 1 calc R . . H59B H 1.0244 0.4414 0.8016 0.048 Uiso 1 1 calc R . . C60 C 0.91626(9) 0.42660(10) 0.79053(13) 0.0362(4) Uani 1 1 d . . . H60A H 0.9216 0.4343 0.7300 0.043 Uiso 1 1 calc R . . H60B H 0.9058 0.3774 0.8002 0.043 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 0.0254(13) 0.0285(13) 0.0370(16) 0.0014(11) -0.0025(11) 0.0017(11) Li2 0.0252(13) 0.0290(13) 0.0353(15) 0.0018(11) -0.0021(11) 0.0008(11) Li3 0.0295(13) 0.0236(13) 0.0404(16) -0.0017(11) -0.0006(12) 0.0022(11) Li4 0.0220(12) 0.0288(13) 0.0397(16) -0.0022(12) -0.0033(11) 0.0015(10) N1 0.0438(9) 0.0411(9) 0.0745(13) 0.0174(9) -0.0221(9) 0.0002(8) N2 0.0312(7) 0.0299(7) 0.0463(9) 0.0029(6) -0.0067(7) 0.0041(6) N3 0.0406(8) 0.0344(8) 0.0519(10) 0.0076(7) -0.0149(8) 0.0006(7) N4 0.0312(7) 0.0304(7) 0.0440(9) 0.0040(6) -0.0040(6) 0.0030(6) O1 0.0253(5) 0.0272(6) 0.0306(6) 0.0014(5) -0.0042(5) 0.0032(4) O2 0.0297(6) 0.0279(6) 0.0438(7) 0.0083(5) -0.0099(5) 0.0009(5) O3 0.0203(5) 0.0328(6) 0.0531(8) -0.0090(6) 0.0009(5) -0.0005(5) O4 0.0236(5) 0.0408(7) 0.0291(6) 0.0010(5) -0.0019(5) -0.0009(5) O5 0.0595(10) 0.0284(6) 0.0838(12) -0.0134(7) 0.0386(9) -0.0076(6) O6 0.0268(6) 0.0547(8) 0.0308(6) -0.0002(6) -0.0021(5) -0.0114(5) O7 0.0271(5) 0.0240(5) 0.0346(6) -0.0021(5) -0.0063(5) 0.0040(4) O8 0.0267(6) 0.0278(6) 0.0414(7) 0.0065(5) -0.0075(5) 0.0007(4) O9 0.0298(6) 0.0377(7) 0.0370(6) -0.0116(5) 0.0038(5) -0.0067(5) O10 0.0501(8) 0.0267(6) 0.0529(8) -0.0049(6) 0.0201(7) -0.0005(6) O11 0.0227(6) 0.0372(6) 0.0337(6) -0.0047(5) -0.0041(5) 0.0021(4) O12 0.0233(6) 0.0311(6) 0.0662(9) -0.0027(6) 0.0037(6) -0.0007(5) C1 0.0294(8) 0.0335(9) 0.0459(10) 0.0082(8) -0.0101(8) -0.0045(7) C2 0.0217(7) 0.0276(8) 0.0327(8) 0.0063(6) -0.0017(6) 0.0000(6) C3 0.0232(7) 0.0293(8) 0.0290(8) 0.0035(6) -0.0039(6) -0.0038(6) C4 0.0254(7) 0.0250(7) 0.0275(8) -0.0003(6) -0.0001(6) -0.0019(6) C5 0.0198(7) 0.0255(7) 0.0235(7) 0.0012(6) 0.0015(5) 0.0008(5) C6 0.0220(7) 0.0270(7) 0.0279(8) 0.0010(6) -0.0040(6) -0.0024(6) C7 0.0257(7) 0.0227(7) 0.0314(8) 0.0025(6) -0.0020(6) -0.0035(6) C8 0.0247(7) 0.0280(8) 0.0324(8) -0.0009(6) -0.0006(6) 0.0011(6) C9 0.0236(7) 0.0249(7) 0.0303(8) 0.0034(6) 0.0001(6) 0.0029(6) C10 0.0361(9) 0.0232(7) 0.0307(8) -0.0001(6) -0.0012(7) 0.0008(6) C11 0.0321(8) 0.0284(8) 0.0317(8) 0.0005(7) -0.0086(7) -0.0005(6) C12 0.0237(7) 0.0289(8) 0.0318(8) 0.0044(6) -0.0010(6) 0.0002(6) C13 0.0302(8) 0.0252(8) 0.0387(9) 0.0021(7) -0.0055(7) -0.0023(6) C14 0.0271(8) 0.0255(8) 0.0329(8) 0.0013(6) -0.0049(6) -0.0008(6) C15 0.0310(9) 0.0331(9) 0.0589(12) -0.0080(9) 0.0010(8) -0.0017(7) C16 0.0304(9) 0.0399(10) 0.0663(14) -0.0082(9) 0.0043(9) -0.0060(8) C17 0.0224(8) 0.0384(9) 0.0406(10) -0.0047(7) 0.0008(7) 0.0013(6) C18 0.0248(8) 0.0399(10) 0.0443(10) -0.0086(8) 0.0003(7) 0.0026(7) C19 0.0232(8) 0.0537(11) 0.0333(9) -0.0039(8) -0.0025(7) 0.0051(7) C20 0.0285(9) 0.0561(12) 0.0418(10) -0.0009(9) 0.0017(8) -0.0101(8) C21 0.0278(14) 0.0372(19) 0.0275(13) -0.0058(11) 0.0006(10) 0.0041(12) C21A 0.036(5) 0.076(9) 0.045(4) 0.012(5) -0.014(4) -0.015(5) C22 0.0316(9) 0.0669(13) 0.0315(9) 0.0006(9) -0.0075(8) -0.0096(9) C23 0.031(2) 0.0324(19) 0.042(3) -0.0021(16) 0.0055(19) -0.0032(15) C23A 0.036(2) 0.043(2) 0.052(3) -0.006(2) 0.011(2) -0.0069(18) C24 0.0467(12) 0.0563(13) 0.0508(12) -0.0068(10) 0.0089(10) 0.0065(10) C25 0.050(3) 0.040(3) 0.052(4) -0.002(3) -0.003(3) 0.012(2) C25A 0.040(3) 0.030(2) 0.061(6) -0.014(3) -0.007(3) 0.004(2) C26 0.0418(10) 0.0290(8) 0.0387(9) -0.0070(7) -0.0065(8) -0.0051(7) C27 0.0370(9) 0.0594(12) 0.0330(9) 0.0032(9) -0.0073(8) -0.0132(9) C28 0.0358(9) 0.0442(10) 0.0511(11) 0.0094(9) -0.0069(9) -0.0099(8) C29 0.0418(10) 0.0430(10) 0.0425(10) 0.0027(8) -0.0031(8) -0.0105(8) C30 0.0359(9) 0.0439(10) 0.0302(9) -0.0004(7) -0.0034(7) -0.0089(8) C31 0.0304(8) 0.0289(8) 0.0365(9) 0.0015(7) -0.0037(7) -0.0023(7) C32 0.0238(7) 0.0269(8) 0.0275(8) 0.0030(6) 0.0000(6) 0.0014(6) C33 0.0251(7) 0.0233(7) 0.0316(8) -0.0015(6) 0.0019(6) -0.0015(6) C34 0.0217(7) 0.0259(7) 0.0288(8) -0.0020(6) -0.0020(6) -0.0007(6) C35 0.0218(7) 0.0263(7) 0.0273(8) -0.0026(6) 0.0009(6) 0.0020(6) C36 0.0254(7) 0.0233(7) 0.0323(8) -0.0005(6) -0.0013(6) -0.0024(6) C37 0.0223(7) 0.0299(8) 0.0300(8) -0.0006(6) -0.0040(6) -0.0021(6) C38 0.0250(7) 0.0272(8) 0.0334(8) -0.0008(6) 0.0013(6) -0.0022(6) C39 0.0254(7) 0.0254(7) 0.0271(8) 0.0005(6) 0.0018(6) 0.0014(6) C40 0.0336(8) 0.0232(7) 0.0358(9) 0.0004(6) -0.0052(7) -0.0044(6) C41 0.0304(8) 0.0275(8) 0.0356(9) 0.0022(7) -0.0067(7) -0.0056(6) C42 0.0213(7) 0.0255(7) 0.0317(8) 0.0022(6) 0.0011(6) 0.0001(6) C43 0.0247(7) 0.0219(7) 0.0345(8) -0.0009(6) -0.0005(6) 0.0005(6) C44 0.0228(7) 0.0259(7) 0.0310(8) -0.0031(6) -0.0001(6) -0.0002(6) C45 0.0468(11) 0.0428(10) 0.0377(10) -0.0108(8) 0.0009(8) -0.0155(9) C46 0.0386(10) 0.0461(11) 0.0498(12) 0.0018(9) -0.0081(9) -0.0121(8) C47 0.0308(10) 0.0631(14) 0.0721(15) -0.0187(12) -0.0038(10) -0.0019(9) C48 0.0296(9) 0.0482(11) 0.0492(11) -0.0196(9) 0.0027(8) -0.0025(8) C49 0.0509(12) 0.0375(10) 0.0553(13) 0.0002(9) 0.0092(10) -0.0033(9) C50 0.0401(10) 0.0441(11) 0.0474(11) 0.0024(9) 0.0055(9) 0.0023(8) C51 0.0455(11) 0.0370(10) 0.0712(15) 0.0045(10) 0.0107(11) 0.0088(9) C52 0.0397(9) 0.0271(8) 0.0396(9) -0.0046(7) 0.0016(8) 0.0004(7) C53 0.0217(7) 0.0361(9) 0.0395(9) -0.0073(7) -0.0036(7) 0.0045(6) C54 0.0258(8) 0.0341(9) 0.0419(10) -0.0036(7) -0.0005(7) -0.0014(7) C55 0.0339(9) 0.0324(8) 0.0360(9) -0.0043(7) -0.0036(7) 0.0005(7) C56 0.0296(8) 0.0392(9) 0.0359(9) -0.0047(7) -0.0063(7) 0.0010(7) C57 0.0361(11) 0.0323(10) 0.116(2) -0.0081(12) 0.0010(13) -0.0061(8) C58 0.0438(13) 0.0740(18) 0.109(3) -0.0449(17) -0.0082(15) -0.0012(12) C59 0.0232(8) 0.0529(11) 0.0441(11) -0.0028(9) 0.0004(8) 0.0011(7) C60 0.0255(8) 0.0381(9) 0.0448(10) -0.0039(8) 0.0011(7) 0.0014(7) _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 O2 1.900(3) . ? Li1 O1 1.902(3) . ? Li1 O3 1.955(3) . ? Li1 O4 1.973(3) . ? Li1 Li2 2.668(4) . ? Li2 O1 1.907(3) . ? Li2 O2 1.915(3) . ? Li2 O5 1.940(3) . ? Li2 O6 1.952(3) . ? Li3 O7 1.904(3) . ? Li3 O8 1.912(3) . ? Li3 O9 1.952(3) . ? Li3 O10 1.955(3) . ? Li3 Li4 2.664(4) . ? Li4 O8 1.889(3) . ? Li4 O7 1.893(3) . ? Li4 O12 1.965(3) . ? Li4 O11 1.979(3) . ? N1 C1 1.148(2) . ? N2 C8 1.150(2) . ? N3 C31 1.149(2) . ? N4 C38 1.149(2) . ? O1 C5 1.2996(18) . ? O2 C12 1.293(2) . ? O3 C18 1.439(2) . ? O3 C15 1.448(2) . ? O4 C19 1.448(2) . ? O4 C22 1.450(2) . ? O5 C26 1.425(2) . ? O5 C23 1.461(4) . ? O5 C23A 1.546(5) . ? O6 C30 1.437(2) . ? O6 C27 1.453(2) . ? O7 C35 1.2958(19) . ? O8 C42 1.2957(19) . ? O9 C48 1.447(2) . ? O9 C45 1.448(2) . ? O10 C52 1.429(2) . ? O10 C49 1.445(2) . ? O11 C56 1.448(2) . ? O11 C53 1.4502(19) . ? O12 C60 1.441(2) . ? O12 C57 1.444(3) . ? C1 C2 1.436(2) . ? C2 C3 1.399(2) . ? C2 C7 1.402(2) . ? C3 C4 1.380(2) . ? C3 H3 0.9500 . ? C4 C5 1.424(2) . ? C4 H4 0.9500 . ? C5 C6 1.418(2) . ? C6 C7 1.381(2) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.426(2) . ? C9 C10 1.396(2) . ? C9 C14 1.408(2) . ? C10 C11 1.380(2) . ? C10 H10 0.9500 . ? C11 C12 1.418(2) . ? C11 H11 0.9500 . ? C12 C13 1.420(2) . ? C13 C14 1.377(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.511(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.532(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.514(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.511(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.499(3) . ? C20 C21A 1.590(9) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.509(4) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C21A C22 1.394(8) . ? C21A H21C 0.9900 . ? C21A H21D 0.9900 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.496(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C23A C24 1.541(5) . ? C23A H23C 0.9900 . ? C23A H23D 0.9900 . ? C24 C25A 1.499(9) . ? C24 C25 1.529(7) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.527(8) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C25A C26 1.487(9) . ? C25A H25C 0.9900 . ? C25A H25D 0.9900 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.524(3) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.494(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.516(3) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.432(2) . ? C32 C33 1.402(2) . ? C32 C37 1.404(2) . ? C33 C34 1.373(2) . ? C33 H33 0.9500 . ? C34 C35 1.423(2) . ? C34 H34 0.9500 . ? C35 C36 1.417(2) . ? C36 C37 1.378(2) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? C38 C39 1.431(2) . ? C39 C40 1.403(2) . ? C39 C44 1.406(2) . ? C40 C41 1.376(2) . ? C40 H40 0.9500 . ? C41 C42 1.421(2) . ? C41 H41 0.9500 . ? C42 C43 1.420(2) . ? C43 C44 1.373(2) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? C45 C46 1.507(3) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46 C47 1.511(3) . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? C47 C48 1.532(3) . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? C49 C50 1.503(3) . ? C49 H49A 0.9900 . ? C49 H49B 0.9900 . ? C50 C51 1.520(3) . ? C50 H50A 0.9900 . ? C50 H50B 0.9900 . ? C51 C52 1.516(3) . ? C51 H51A 0.9900 . ? C51 H51B 0.9900 . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C53 C54 1.505(3) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C54 C55 1.524(2) . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? C55 C56 1.519(3) . ? C55 H55A 0.9900 . ? C55 H55B 0.9900 . ? C56 H56A 0.9900 . ? C56 H56B 0.9900 . ? C57 C58 1.463(3) . ? C57 H57A 0.9900 . ? C57 H57B 0.9900 . ? C58 C59 1.508(3) . ? C58 H58A 0.9900 . ? C58 H58B 0.9900 . ? C59 C60 1.516(3) . ? C59 H59A 0.9900 . ? C59 H59B 0.9900 . ? C60 H60A 0.9900 . ? C60 H60B 0.9900 . ? 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 O2 Li1 O1 91.41(13) . . ? O2 Li1 O3 114.93(15) . . ? O1 Li1 O3 118.78(17) . . ? O2 Li1 O4 113.97(16) . . ? O1 Li1 O4 111.12(14) . . ? O3 Li1 O4 106.43(15) . . ? O2 Li1 Li2 45.85(9) . . ? O1 Li1 Li2 45.60(9) . . ? O3 Li1 Li2 131.89(16) . . ? O4 Li1 Li2 121.67(14) . . ? O1 Li2 O2 90.79(13) . . ? O1 Li2 O5 117.70(16) . . ? O2 Li2 O5 110.82(15) . . ? O1 Li2 O6 119.55(15) . . ? O2 Li2 O6 114.53(16) . . ? O5 Li2 O6 103.46(15) . . ? O1 Li2 Li1 45.46(10) . . ? O2 Li2 Li1 45.38(9) . . ? O5 Li2 Li1 127.32(15) . . ? O6 Li2 Li1 128.70(16) . . ? O7 Li3 O8 90.38(13) . . ? O7 Li3 O9 122.12(16) . . ? O8 Li3 O9 115.02(17) . . ? O7 Li3 O10 111.41(16) . . ? O8 Li3 O10 115.37(16) . . ? O9 Li3 O10 103.06(14) . . ? O7 Li3 Li4 45.26(9) . . ? O8 Li3 Li4 45.13(10) . . ? O9 Li3 Li4 133.45(16) . . ? O10 Li3 Li4 123.44(15) . . ? O8 Li4 O7 91.44(13) . . ? O8 Li4 O12 112.08(14) . . ? O7 Li4 O12 120.19(17) . . ? O8 Li4 O11 118.39(17) . . ? O7 Li4 O11 109.79(14) . . ? O12 Li4 O11 105.34(14) . . ? O8 Li4 Li3 45.85(10) . . ? O7 Li4 Li3 45.60(10) . . ? O12 Li4 Li3 128.17(15) . . ? O11 Li4 Li3 126.49(15) . . ? C5 O1 Li1 130.35(13) . . ? C5 O1 Li2 135.72(13) . . ? Li1 O1 Li2 88.94(13) . . ? C12 O2 Li1 136.74(14) . . ? C12 O2 Li2 132.88(14) . . ? Li1 O2 Li2 88.77(13) . . ? C18 O3 C15 109.56(13) . . ? C18 O3 Li1 119.91(13) . . ? C15 O3 Li1 127.63(14) . . ? C19 O4 C22 108.01(14) . . ? C19 O4 Li1 111.68(14) . . ? C22 O4 Li1 120.79(14) . . ? C26 O5 C23 109.67(19) . . ? C26 O5 C23A 104.4(2) . . ? C26 O5 Li2 132.36(15) . . ? C23 O5 Li2 117.53(19) . . ? C23A O5 Li2 110.4(2) . . ? C30 O6 C27 108.80(13) . . ? C30 O6 Li2 122.52(13) . . ? C27 O6 Li2 128.64(14) . . ? C35 O7 Li4 132.28(14) . . ? C35 O7 Li3 138.08(14) . . ? Li4 O7 Li3 89.13(13) . . ? C42 O8 Li4 138.98(14) . . ? C42 O8 Li3 130.77(14) . . ? Li4 O8 Li3 89.02(13) . . ? C48 O9 C45 109.09(14) . . ? C48 O9 Li3 115.03(13) . . ? C45 O9 Li3 128.11(14) . . ? C52 O10 C49 108.77(14) . . ? C52 O10 Li3 132.12(15) . . ? C49 O10 Li3 114.49(14) . . ? C56 O11 C53 108.56(14) . . ? C56 O11 Li4 117.65(13) . . ? C53 O11 Li4 116.67(13) . . ? C60 O12 C57 108.48(14) . . ? C60 O12 Li4 122.22(14) . . ? C57 O12 Li4 126.19(16) . . ? N1 C1 C2 179.0(2) . . ? C3 C2 C7 119.35(14) . . ? C3 C2 C1 119.91(15) . . ? C7 C2 C1 120.73(15) . . ? C4 C3 C2 120.54(15) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 121.33(15) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? O1 C5 C6 121.65(14) . . ? O1 C5 C4 121.49(14) . . ? C6 C5 C4 116.86(14) . . ? C7 C6 C5 121.67(14) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C6 C7 C2 120.23(15) . . ? C6 C7 H7 119.9 . . ? C2 C7 H7 119.9 . . ? N2 C8 C9 178.11(19) . . ? C10 C9 C14 118.59(15) . . ? C10 C9 C8 121.52(15) . . ? C14 C9 C8 119.88(15) . . ? C11 C10 C9 120.71(15) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 121.89(16) . . ? C10 C11 H11 119.1 . . ? C12 C11 H11 119.1 . . ? O2 C12 C11 121.59(15) . . ? O2 C12 C13 122.05(15) . . ? C11 C12 C13 116.35(15) . . ? C14 C13 C12 121.73(15) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C13 C14 C9 120.71(15) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? O3 C15 C16 106.15(15) . . ? O3 C15 H15A 110.5 . . ? C16 C15 H15A 110.5 . . ? O3 C15 H15B 110.5 . . ? C16 C15 H15B 110.5 . . ? H15A C15 H15B 108.7 . . ? C15 C16 C17 103.22(15) . . ? C15 C16 H16A 111.1 . . ? C17 C16 H16A 111.1 . . ? C15 C16 H16B 111.1 . . ? C17 C16 H16B 111.1 . . ? H16A C16 H16B 109.1 . . ? C18 C17 C16 101.17(15) . . ? C18 C17 H17A 111.5 . . ? C16 C17 H17A 111.5 . . ? C18 C17 H17B 111.5 . . ? C16 C17 H17B 111.5 . . ? H17A C17 H17B 109.4 . . ? O3 C18 C17 105.47(14) . . ? O3 C18 H18A 110.6 . . ? C17 C18 H18A 110.6 . . ? O3 C18 H18B 110.6 . . ? C17 C18 H18B 110.6 . . ? H18A C18 H18B 108.8 . . ? O4 C19 C20 105.86(15) . . ? O4 C19 H19A 110.6 . . ? C20 C19 H19A 110.6 . . ? O4 C19 H19B 110.6 . . ? C20 C19 H19B 110.6 . . ? H19A C19 H19B 108.7 . . ? C21 C20 C19 101.56(18) . . ? C19 C20 C21A 104.8(3) . . ? C21 C20 H20A 111.5 . . ? C19 C20 H20A 111.5 . . ? C21A C20 H20A 83.5 . . ? C21 C20 H20B 111.5 . . ? C19 C20 H20B 111.5 . . ? C21A C20 H20B 132.6 . . ? H20A C20 H20B 109.3 . . ? C20 C21 C22 103.5(2) . . ? C20 C21 H21A 111.1 . . ? C22 C21 H21A 111.1 . . ? C20 C21 H21B 111.1 . . ? C22 C21 H21B 111.1 . . ? H21A C21 H21B 109.0 . . ? C22 C21A C20 104.5(6) . . ? C22 C21A H21C 110.9 . . ? C20 C21A H21C 110.9 . . ? C22 C21A H21D 110.9 . . ? C20 C21A H21D 110.9 . . ? H21C C21A H21D 108.9 . . ? C21A C22 O4 109.5(4) . . ? O4 C22 C21 106.61(18) . . ? C21A C22 H22A 80.8 . . ? O4 C22 H22A 110.4 . . ? C21 C22 H22A 110.4 . . ? C21A C22 H22B 132.0 . . ? O4 C22 H22B 110.4 . . ? C21 C22 H22B 110.4 . . ? H22A C22 H22B 108.6 . . ? O5 C23 C24 104.8(3) . . ? O5 C23 H23A 110.8 . . ? C24 C23 H23A 110.8 . . ? O5 C23 H23B 110.8 . . ? C24 C23 H23B 110.8 . . ? H23A C23 H23B 108.9 . . ? C24 C23A O5 98.8(3) . . ? C24 C23A H23C 112.0 . . ? O5 C23A H23C 112.0 . . ? C24 C23A H23D 112.0 . . ? O5 C23A H23D 112.0 . . ? H23C C23A H23D 109.7 . . ? C23 C24 C25A 109.4(4) . . ? C23 C24 C25 104.1(4) . . ? C25A C24 C23A 101.7(5) . . ? C25 C24 C23A 85.7(5) . . ? C23 C24 H24A 110.9 . . ? C25A C24 H24A 89.0 . . ? C25 C24 H24A 110.9 . . ? C23A C24 H24A 145.2 . . ? C23 C24 H24B 110.9 . . ? C25A C24 H24B 125.3 . . ? C25 C24 H24B 110.9 . . ? C23A C24 H24B 91.8 . . ? H24A C24 H24B 108.9 . . ? C26 C25 C24 100.9(4) . . ? C26 C25 H25A 111.6 . . ? C24 C25 H25A 111.6 . . ? C26 C25 H25B 111.6 . . ? C24 C25 H25B 111.6 . . ? H25A C25 H25B 109.4 . . ? C26 C25A C24 104.1(5) . . ? C26 C25A H25C 110.9 . . ? C24 C25A H25C 110.9 . . ? C26 C25A H25D 110.9 . . ? C24 C25A H25D 110.9 . . ? H25C C25A H25D 108.9 . . ? O5 C26 C25A 109.4(3) . . ? O5 C26 C25 100.5(4) . . ? O5 C26 H26A 111.7 . . ? C25A C26 H26A 123.2 . . ? C25 C26 H26A 111.7 . . ? O5 C26 H26B 111.7 . . ? C25A C26 H26B 89.2 . . ? C25 C26 H26B 111.7 . . ? H26A C26 H26B 109.5 . . ? O6 C27 C28 105.47(15) . . ? O6 C27 H27A 110.6 . . ? C28 C27 H27A 110.6 . . ? O6 C27 H27B 110.6 . . ? C28 C27 H27B 110.6 . . ? H27A C27 H27B 108.8 . . ? C29 C28 C27 102.96(16) . . ? C29 C28 H28A 111.2 . . ? C27 C28 H28A 111.2 . . ? C29 C28 H28B 111.2 . . ? C27 C28 H28B 111.2 . . ? H28A C28 H28B 109.1 . . ? C28 C29 C30 101.86(16) . . ? C28 C29 H29A 111.4 . . ? C30 C29 H29A 111.4 . . ? C28 C29 H29B 111.4 . . ? C30 C29 H29B 111.4 . . ? H29A C29 H29B 109.3 . . ? O6 C30 C29 106.36(15) . . ? O6 C30 H30A 110.5 . . ? C29 C30 H30A 110.5 . . ? O6 C30 H30B 110.5 . . ? C29 C30 H30B 110.5 . . ? H30A C30 H30B 108.6 . . ? N3 C31 C32 178.64(19) . . ? C33 C32 C37 118.75(14) . . ? C33 C32 C31 121.21(15) . . ? C37 C32 C31 120.03(15) . . ? C34 C33 C32 120.65(15) . . ? C34 C33 H33 119.7 . . ? C32 C33 H33 119.7 . . ? C33 C34 C35 121.69(14) . . ? C33 C34 H34 119.2 . . ? C35 C34 H34 119.2 . . ? O7 C35 C36 121.80(15) . . ? O7 C35 C34 121.51(14) . . ? C36 C35 C34 116.69(14) . . ? C37 C36 C35 121.50(15) . . ? C37 C36 H36 119.2 . . ? C35 C36 H36 119.2 . . ? C36 C37 C32 120.72(15) . . ? C36 C37 H37 119.6 . . ? C32 C37 H37 119.6 . . ? N4 C38 C39 178.91(19) . . ? C40 C39 C44 118.73(15) . . ? C40 C39 C38 121.46(15) . . ? C44 C39 C38 119.80(15) . . ? C41 C40 C39 120.64(15) . . ? C41 C40 H40 119.7 . . ? C39 C40 H40 119.7 . . ? C40 C41 C42 121.60(15) . . ? C40 C41 H41 119.2 . . ? C42 C41 H41 119.2 . . ? O8 C42 C43 122.18(14) . . ? O8 C42 C41 121.12(15) . . ? C43 C42 C41 116.70(15) . . ? C44 C43 C42 121.64(15) . . ? C44 C43 H43 119.2 . . ? C42 C43 H43 119.2 . . ? C43 C44 C39 120.69(15) . . ? C43 C44 H44 119.7 . . ? C39 C44 H44 119.7 . . ? O9 C45 C46 105.80(15) . . ? O9 C45 H45A 110.6 . . ? C46 C45 H45A 110.6 . . ? O9 C45 H45B 110.6 . . ? C46 C45 H45B 110.6 . . ? H45A C45 H45B 108.7 . . ? C45 C46 C47 102.73(17) . . ? C45 C46 H46A 111.2 . . ? C47 C46 H46A 111.2 . . ? C45 C46 H46B 111.2 . . ? C47 C46 H46B 111.2 . . ? H46A C46 H46B 109.1 . . ? C46 C47 C48 101.20(18) . . ? C46 C47 H47A 111.5 . . ? C48 C47 H47A 111.5 . . ? C46 C47 H47B 111.5 . . ? C48 C47 H47B 111.5 . . ? H47A C47 H47B 109.3 . . ? O9 C48 C47 105.60(16) . . ? O9 C48 H48A 110.6 . . ? C47 C48 H48A 110.6 . . ? O9 C48 H48B 110.6 . . ? C47 C48 H48B 110.6 . . ? H48A C48 H48B 108.8 . . ? O10 C49 C50 107.38(16) . . ? O10 C49 H49A 110.2 . . ? C50 C49 H49A 110.2 . . ? O10 C49 H49B 110.2 . . ? C50 C49 H49B 110.2 . . ? H49A C49 H49B 108.5 . . ? C49 C50 C51 102.83(17) . . ? C49 C50 H50A 111.2 . . ? C51 C50 H50A 111.2 . . ? C49 C50 H50B 111.2 . . ? C51 C50 H50B 111.2 . . ? H50A C50 H50B 109.1 . . ? C52 C51 C50 102.15(17) . . ? C52 C51 H51A 111.3 . . ? C50 C51 H51A 111.3 . . ? C52 C51 H51B 111.3 . . ? C50 C51 H51B 111.3 . . ? H51A C51 H51B 109.2 . . ? O10 C52 C51 103.67(15) . . ? O10 C52 H52A 111.0 . . ? C51 C52 H52A 111.0 . . ? O10 C52 H52B 111.0 . . ? C51 C52 H52B 111.0 . . ? H52A C52 H52B 109.0 . . ? O11 C53 C54 105.55(14) . . ? O11 C53 H53A 110.6 . . ? C54 C53 H53A 110.6 . . ? O11 C53 H53B 110.6 . . ? C54 C53 H53B 110.6 . . ? H53A C53 H53B 108.8 . . ? C53 C54 C55 101.65(14) . . ? C53 C54 H54A 111.4 . . ? C55 C54 H54A 111.4 . . ? C53 C54 H54B 111.4 . . ? C55 C54 H54B 111.4 . . ? H54A C54 H54B 109.3 . . ? C56 C55 C54 101.66(15) . . ? C56 C55 H55A 111.4 . . ? C54 C55 H55A 111.4 . . ? C56 C55 H55B 111.4 . . ? C54 C55 H55B 111.4 . . ? H55A C55 H55B 109.3 . . ? O11 C56 C55 106.44(14) . . ? O11 C56 H56A 110.4 . . ? C55 C56 H56A 110.4 . . ? O11 C56 H56B 110.4 . . ? C55 C56 H56B 110.4 . . ? H56A C56 H56B 108.6 . . ? O12 C57 C58 107.82(19) . . ? O12 C57 H57A 110.1 . . ? C58 C57 H57A 110.1 . . ? O12 C57 H57B 110.1 . . ? C58 C57 H57B 110.1 . . ? H57A C57 H57B 108.5 . . ? C57 C58 C59 106.2(2) . . ? C57 C58 H58A 110.5 . . ? C59 C58 H58A 110.5 . . ? C57 C58 H58B 110.5 . . ? C59 C58 H58B 110.5 . . ? H58A C58 H58B 108.7 . . ? C58 C59 C60 102.18(17) . . ? C58 C59 H59A 111.3 . . ? C60 C59 H59A 111.3 . . ? C58 C59 H59B 111.3 . . ? C60 C59 H59B 111.3 . . ? H59A C59 H59B 109.2 . . ? O12 C60 C59 105.43(15) . . ? O12 C60 H60A 110.7 . . ? C59 C60 H60A 110.7 . . ? O12 C60 H60B 110.7 . . ? C59 C60 H60B 110.7 . . ? H60A C60 H60B 108.8 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.519 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.046 _exptl_crystal_recrystallization_method 'Slow cooling of a saturated THF solution in a water bath from 340K to ambient ' # Attachment '2a-revised.cif' data_kengone2 _database_code_depnum_ccdc_archive 'CCDC 287370' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'lithium 4-methoxyphenoxide pyridine' _chemical_melting_point ? _chemical_formula_moiety 'C48 H48 Li4 N4 O8' _chemical_formula_sum 'C48 H48 Li4 N4 O8' _chemical_formula_weight 836.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Li Li -0.0003 0.0001 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M I41/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z' '-y+3/4, x+1/4, z+1/4' 'y+1/4, -x+1/4, z+1/4' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1, z+1/2' '-y+5/4, x+3/4, z+3/4' 'y+3/4, -x+3/4, z+3/4' '-x, -y, -z' 'x, y-1/2, -z' 'y-3/4, -x-1/4, -z-1/4' '-y-1/4, x-1/4, -z-1/4' '-x+1/2, -y+1/2, -z+1/2' 'x+1/2, y, -z+1/2' 'y-1/4, -x+1/4, -z+1/4' '-y+1/4, x+1/4, -z+1/4' _cell_length_a 17.0224(4) _cell_length_b 17.0224(4) _cell_length_c 15.5545(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4507.11(19) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 2680 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour 'clear colourless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1760 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _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 'Nonius Kappa CCD' _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 5032 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0587 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.43 _reflns_number_total 2579 _reflns_number_gt 1631 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Denzo & Collect' _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0398P)^2^+1.7128P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2579 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0955 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1008 _refine_ls_wR_factor_gt 0.0860 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 0.46558(16) 0.31792(15) -0.06383(15) 0.0286(6) Uani 1 1 d . . . O1 O 0.42451(6) 0.20982(6) -0.06091(6) 0.0265(3) Uani 1 1 d . . . O2 O 0.15634(7) 0.11257(8) 0.11216(7) 0.0436(4) Uani 1 1 d . . . N3 N 0.41376(8) 0.37884(8) 0.03531(8) 0.0296(3) Uani 1 1 d . . . C1 C 0.35893(9) 0.18741(8) -0.02002(9) 0.0237(4) Uani 1 1 d . . . C2 C 0.36165(10) 0.13946(9) 0.05319(10) 0.0263(4) Uani 1 1 d . . . C3 C 0.29359(10) 0.11574(10) 0.09462(10) 0.0296(4) Uani 1 1 d . . . C4 C 0.22065(9) 0.13914(9) 0.06512(10) 0.0295(4) Uani 1 1 d . . . C5 C 0.21601(10) 0.18714(10) -0.00630(10) 0.0301(4) Uani 1 1 d . . . C6 C 0.28442(9) 0.21078(10) -0.04826(10) 0.0279(4) Uani 1 1 d . . . C7 C 0.08121(12) 0.11965(15) 0.07402(14) 0.0500(5) Uani 1 1 d . . . C8 C 0.38389(9) 0.45160(10) 0.03342(11) 0.0293(4) Uani 1 1 d . . . C9 C 0.34434(10) 0.48551(10) 0.10149(11) 0.0335(4) Uani 1 1 d . . . C10 C 0.33489(11) 0.44261(11) 0.17569(11) 0.0375(4) Uani 1 1 d . . . C11 C 0.36503(11) 0.36745(11) 0.17945(11) 0.0369(4) Uani 1 1 d . . . C12 C 0.40377(10) 0.33827(10) 0.10836(10) 0.0333(4) Uani 1 1 d . . . H2 H 0.4131(10) 0.1204(9) 0.0741(9) 0.035(4) Uiso 1 1 d . . . H3 H 0.2965(9) 0.0815(9) 0.1439(11) 0.036(4) Uiso 1 1 d . . . H5 H 0.1659(10) 0.2046(9) -0.0274(10) 0.034(5) Uiso 1 1 d . . . H6 H 0.2817(10) 0.2446(10) -0.0977(11) 0.041(5) Uiso 1 1 d . . . H7A H 0.0644(12) 0.1797(13) 0.0668(13) 0.071(7) Uiso 1 1 d . . . H7B H 0.0789(11) 0.0961(12) 0.0155(14) 0.064(6) Uiso 1 1 d . . . H7C H 0.0454(12) 0.0915(11) 0.1135(12) 0.054(6) Uiso 1 1 d . . . H8 H 0.3916(9) 0.4810(9) -0.0197(11) 0.033(4) Uiso 1 1 d . . . H9 H 0.3246(9) 0.5387(11) 0.0952(10) 0.041(5) Uiso 1 1 d . . . H10 H 0.3102(10) 0.4651(10) 0.2241(12) 0.043(5) Uiso 1 1 d . . . H11 H 0.3609(9) 0.3360(9) 0.2314(10) 0.037(5) Uiso 1 1 d . . . H12 H 0.4239(9) 0.2854(10) 0.1082(10) 0.032(4) 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 Li1 0.0356(16) 0.0275(14) 0.0226(13) -0.0014(11) 0.0015(11) 0.0015(12) O1 0.0284(6) 0.0285(6) 0.0226(5) 0.0016(5) 0.0044(5) -0.0016(5) O2 0.0321(7) 0.0655(9) 0.0332(7) 0.0009(6) 0.0082(5) -0.0127(6) N3 0.0330(8) 0.0288(8) 0.0271(7) -0.0032(6) -0.0008(6) 0.0012(6) C1 0.0289(9) 0.0211(8) 0.0212(8) -0.0041(6) 0.0024(7) -0.0022(7) C2 0.0289(9) 0.0264(9) 0.0235(8) 0.0013(7) -0.0019(7) 0.0003(7) C3 0.0379(10) 0.0300(9) 0.0209(8) 0.0033(7) 0.0006(7) -0.0052(7) C4 0.0289(9) 0.0367(10) 0.0229(8) -0.0065(7) 0.0047(7) -0.0061(8) C5 0.0254(9) 0.0385(10) 0.0262(9) -0.0052(7) -0.0017(7) 0.0048(8) C6 0.0334(9) 0.0294(9) 0.0210(8) 0.0016(7) 0.0000(7) 0.0032(7) C7 0.0311(11) 0.0729(16) 0.0459(13) -0.0118(12) 0.0075(9) -0.0122(11) C8 0.0292(9) 0.0294(9) 0.0293(9) 0.0009(8) -0.0004(7) -0.0008(7) C9 0.0336(10) 0.0285(10) 0.0385(10) -0.0036(8) 0.0047(8) 0.0029(8) C10 0.0429(11) 0.0355(11) 0.0343(10) -0.0087(8) 0.0120(8) -0.0022(8) C11 0.0510(11) 0.0345(10) 0.0253(9) -0.0002(8) 0.0054(8) -0.0038(9) C12 0.0445(11) 0.0259(9) 0.0295(9) -0.0017(8) -0.0036(8) 0.0029(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 O1 1.930(3) 2_655 ? Li1 O1 1.955(3) 11_665 ? Li1 O1 1.969(3) . ? Li1 N3 2.057(3) . ? Li1 Li1 2.592(5) 2_655 ? Li1 Li1 2.642(4) 12_655 ? Li1 Li1 2.642(4) 11_665 ? O1 C1 1.3402(17) . ? O1 Li1 1.930(3) 2_655 ? O1 Li1 1.955(3) 12_655 ? O2 C4 1.3922(19) . ? O2 C7 1.415(2) . ? N3 C8 1.339(2) . ? N3 C12 1.340(2) . ? C1 C6 1.400(2) . ? C1 C2 1.402(2) . ? C2 C3 1.386(2) . ? C2 H2 0.989(17) . ? C3 C4 1.382(2) . ? C3 H3 0.964(17) . ? C4 C5 1.381(2) . ? C5 C6 1.394(2) . ? C5 H5 0.962(17) . ? C6 H6 0.961(18) . ? C7 H7A 1.07(2) . ? C7 H7B 1.00(2) . ? C7 H7C 0.99(2) . ? C8 C9 1.381(2) . ? C8 H8 0.974(16) . ? C9 C10 1.375(2) . ? C9 H9 0.971(18) . ? C10 C11 1.380(2) . ? C10 H10 0.943(18) . ? C11 C12 1.380(2) . ? C11 H11 0.972(16) . ? C12 H12 0.964(17) . ? 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 O1 Li1 O1 95.06(12) 2_655 11_665 ? O1 Li1 O1 96.60(12) 2_655 . ? O1 Li1 O1 93.83(11) 11_665 . ? O1 Li1 N3 121.42(13) 2_655 . ? O1 Li1 N3 133.82(14) 11_665 . ? O1 Li1 N3 107.55(13) . . ? O1 Li1 Li1 48.97(9) 2_655 2_655 ? O1 Li1 Li1 94.67(8) 11_665 2_655 ? O1 Li1 Li1 47.69(9) . 2_655 ? N3 Li1 Li1 130.05(8) . 2_655 ? O1 Li1 Li1 93.72(9) 2_655 12_655 ? O1 Li1 Li1 46.75(10) 11_665 12_655 ? O1 Li1 Li1 47.45(7) . 12_655 ? N3 Li1 Li1 141.23(15) . 12_655 ? Li1 Li1 Li1 60.62(5) 2_655 12_655 ? O1 Li1 Li1 47.55(7) 2_655 11_665 ? O1 Li1 Li1 47.90(10) 11_665 11_665 ? O1 Li1 Li1 92.81(8) . 11_665 ? N3 Li1 Li1 158.66(15) . 11_665 ? Li1 Li1 Li1 60.62(5) 2_655 11_665 ? Li1 Li1 Li1 58.76(11) 12_655 11_665 ? C1 O1 Li1 138.50(12) . 2_655 ? C1 O1 Li1 122.82(12) . 12_655 ? Li1 O1 Li1 85.69(12) 2_655 12_655 ? C1 O1 Li1 124.94(12) . . ? Li1 O1 Li1 83.34(12) 2_655 . ? Li1 O1 Li1 84.65(12) 12_655 . ? C4 O2 C7 117.56(14) . . ? C8 N3 C12 116.55(14) . . ? C8 N3 Li1 127.77(13) . . ? C12 N3 Li1 115.47(13) . . ? O1 C1 C6 121.66(13) . . ? O1 C1 C2 121.58(14) . . ? C6 C1 C2 116.75(14) . . ? C3 C2 C1 121.32(15) . . ? C3 C2 H2 119.5(9) . . ? C1 C2 H2 119.2(9) . . ? C4 C3 C2 120.84(15) . . ? C4 C3 H3 118.9(10) . . ? C2 C3 H3 120.2(10) . . ? C5 C4 C3 119.26(15) . . ? C5 C4 O2 124.74(15) . . ? C3 C4 O2 115.99(14) . . ? C4 C5 C6 119.97(16) . . ? C4 C5 H5 120.6(9) . . ? C6 C5 H5 119.4(9) . . ? C5 C6 C1 121.86(15) . . ? C5 C6 H6 120.5(10) . . ? C1 C6 H6 117.7(10) . . ? O2 C7 H7A 111.6(11) . . ? O2 C7 H7B 112.6(12) . . ? H7A C7 H7B 106.2(16) . . ? O2 C7 H7C 104.8(11) . . ? H7A C7 H7C 111.4(15) . . ? H7B C7 H7C 110.4(15) . . ? N3 C8 C9 123.69(16) . . ? N3 C8 H8 116.3(9) . . ? C9 C8 H8 120.1(9) . . ? C10 C9 C8 118.58(17) . . ? C10 C9 H9 122.7(10) . . ? C8 C9 H9 118.7(10) . . ? C9 C10 C11 118.99(16) . . ? C9 C10 H10 120.4(10) . . ? C11 C10 H10 120.6(10) . . ? C10 C11 C12 118.52(17) . . ? C10 C11 H11 121.3(9) . . ? C12 C11 H11 120.2(9) . . ? N3 C12 C11 123.67(16) . . ? N3 C12 H12 115.7(9) . . ? C11 C12 H12 120.6(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Li1 O1 C1 144.23(11) 2_655 . . . ? O1 Li1 O1 C1 -120.21(13) 11_665 . . . ? N3 Li1 O1 C1 18.29(19) . . . . ? Li1 Li1 O1 C1 146.95(16) 2_655 . . . ? Li1 Li1 O1 C1 -126.77(15) 12_655 . . . ? Li1 Li1 O1 C1 -168.19(12) 11_665 . . . ? O1 Li1 O1 Li1 -2.72(15) 2_655 . . 2_655 ? O1 Li1 O1 Li1 92.83(11) 11_665 . . 2_655 ? N3 Li1 O1 Li1 -128.67(9) . . . 2_655 ? Li1 Li1 O1 Li1 86.28(11) 12_655 . . 2_655 ? Li1 Li1 O1 Li1 44.86(15) 11_665 . . 2_655 ? O1 Li1 O1 Li1 -88.99(12) 2_655 . . 12_655 ? O1 Li1 O1 Li1 6.56(11) 11_665 . . 12_655 ? N3 Li1 O1 Li1 145.06(14) . . . 12_655 ? Li1 Li1 O1 Li1 -86.28(11) 2_655 . . 12_655 ? Li1 Li1 O1 Li1 -41.42(14) 11_665 . . 12_655 ? O1 Li1 N3 C8 114.11(18) 2_655 . . . ? O1 Li1 N3 C8 -22.7(3) 11_665 . . . ? O1 Li1 N3 C8 -136.35(15) . . . . ? Li1 Li1 N3 C8 174.68(19) 2_655 . . . ? Li1 Li1 N3 C8 -94.0(2) 12_655 . . . ? Li1 Li1 N3 C8 61.7(5) 11_665 . . . ? O1 Li1 N3 C12 -71.27(19) 2_655 . . . ? O1 Li1 N3 C12 151.88(18) 11_665 . . . ? O1 Li1 N3 C12 38.27(18) . . . . ? Li1 Li1 N3 C12 -10.7(3) 2_655 . . . ? Li1 Li1 N3 C12 80.6(3) 12_655 . . . ? Li1 Li1 N3 C12 -123.7(4) 11_665 . . . ? Li1 O1 C1 C6 -165.98(15) 2_655 . . . ? Li1 O1 C1 C6 -39.5(2) 12_655 . . . ? Li1 O1 C1 C6 68.84(19) . . . . ? Li1 O1 C1 C2 14.1(2) 2_655 . . . ? Li1 O1 C1 C2 140.54(15) 12_655 . . . ? Li1 O1 C1 C2 -111.08(16) . . . . ? O1 C1 C2 C3 -179.26(14) . . . . ? C6 C1 C2 C3 0.8(2) . . . . ? C1 C2 C3 C4 -0.4(2) . . . . ? C2 C3 C4 C5 -0.4(2) . . . . ? C2 C3 C4 O2 -179.33(14) . . . . ? C7 O2 C4 C5 15.2(2) . . . . ? C7 O2 C4 C3 -165.88(16) . . . . ? C3 C4 C5 C6 0.6(2) . . . . ? O2 C4 C5 C6 179.50(14) . . . . ? C4 C5 C6 C1 -0.2(2) . . . . ? O1 C1 C6 C5 179.53(14) . . . . ? C2 C1 C6 C5 -0.5(2) . . . . ? C12 N3 C8 C9 -0.1(2) . . . . ? Li1 N3 C8 C9 174.49(15) . . . . ? N3 C8 C9 C10 0.1(3) . . . . ? C8 C9 C10 C11 -0.1(3) . . . . ? C9 C10 C11 C12 0.1(3) . . . . ? C8 N3 C12 C11 0.1(2) . . . . ? Li1 N3 C12 C11 -175.12(16) . . . . ? C10 C11 C12 N3 -0.2(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.150 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.039 # Attachment '3a.cif' data_hend22 _database_code_depnum_ccdc_archive 'CCDC 287371' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'lithium 2,6-di-t-butyl-4cyanophenoxide pyridine' _chemical_melting_point ? _chemical_formula_moiety 'C25 H30 Li N3 O' _chemical_formula_sum 'C25 H30 Li N3 O' _chemical_formula_weight 395.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Li Li -0.0003 0.0001 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.2740(1) _cell_length_b 14.9330(2) _cell_length_c 17.3490(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2402.64(5) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 3899 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 30.03 _exptl_crystal_description cube _exptl_crystal_colour 'clear colorless' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.093 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type none _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 'Nonius Kappa CCD' _diffrn_measurement_method '/f and /w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6958 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 30.06 _reflns_number_total 6958 _reflns_number_gt 6500 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect & Denzo' _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; The PLATON ADDSYM routine strongly suggests extra symmetry to sp gr Pnma. However, there is no evidence whatsoever for the systematic absences required by this symmetry + not al atoms map onto equivalents. Thus this suggestion has been ignored. 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^)+(0.0396P)^2^+0.3391P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6958 _refine_ls_number_parameters 391 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.0820 _refine_ls_wR_factor_gt 0.0795 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 Li1 Li 0.30103(18) 0.68778(11) 0.66404(9) 0.0242(3) Uani 1 1 d . . . O1 O 0.25692(8) 0.61719(4) 0.74641(3) 0.02274(13) Uani 1 1 d . . . N1 N 0.28203(10) 0.35513(5) 1.05910(4) 0.02638(17) Uani 1 1 d . . . N2 N 0.52766(9) 0.67023(6) 0.64383(5) 0.02468(16) Uani 1 1 d . . . N3 N 0.26271(9) 0.82760(5) 0.65449(4) 0.02348(15) Uani 1 1 d . . . C1 C 0.25599(9) 0.56627(6) 0.80585(4) 0.01848(15) Uani 1 1 d . . . C2 C 0.26137(10) 0.60398(6) 0.88316(5) 0.01941(15) Uani 1 1 d . . . C3 C 0.26829(10) 0.54716(6) 0.94591(5) 0.02077(16) Uani 1 1 d . . . C4 C 0.26730(10) 0.45371(6) 0.93730(5) 0.02000(16) Uani 1 1 d . . . C5 C 0.25545(10) 0.41642(6) 0.86317(5) 0.01940(15) Uani 1 1 d . . . C6 C 0.24927(9) 0.46935(5) 0.79800(4) 0.01865(15) Uani 1 1 d . . . C7 C 0.27562(10) 0.39829(6) 1.00411(5) 0.02161(17) Uani 1 1 d . . . C8 C 0.25895(12) 0.70581(6) 0.89456(5) 0.02529(18) Uani 1 1 d . . . C9 C 0.25841(18) 0.73181(7) 0.98045(6) 0.0380(3) Uani 1 1 d . . . C10 C 0.12179(15) 0.74514(8) 0.85840(7) 0.0367(3) Uani 1 1 d . . . C11 C 0.39319(15) 0.74902(8) 0.85830(7) 0.0352(2) Uani 1 1 d . . . C12 C 0.23456(10) 0.42692(6) 0.71749(5) 0.02042(16) Uani 1 1 d . . . C13 C 0.22676(12) 0.32414(6) 0.72149(5) 0.02603(18) Uani 1 1 d . . . C14 C 0.09501(11) 0.46045(7) 0.67906(6) 0.02534(19) Uani 1 1 d . . . C15 C 0.36606(11) 0.45061(7) 0.66727(5) 0.02393(18) Uani 1 1 d . . . C16 C 0.59137(11) 0.69055(7) 0.57667(6) 0.0274(2) Uani 1 1 d . . . C17 C 0.73266(12) 0.66853(8) 0.55928(6) 0.0318(2) Uani 1 1 d . . . C18 C 0.81327(13) 0.62310(9) 0.61372(7) 0.0368(2) Uani 1 1 d . . . C19 C 0.74926(13) 0.60126(8) 0.68342(6) 0.0350(2) Uani 1 1 d . . . C20 C 0.60724(11) 0.62571(7) 0.69589(6) 0.0275(2) Uani 1 1 d . . . C21 C 0.37776(11) 0.88182(7) 0.65063(6) 0.02619(19) Uani 1 1 d . . . C22 C 0.37047(11) 0.97140(7) 0.63024(7) 0.0286(2) Uani 1 1 d . . . C23 C 0.23636(12) 1.00777(7) 0.61360(6) 0.0300(2) Uani 1 1 d . . . C24 C 0.11598(11) 0.95347(8) 0.61822(7) 0.0319(2) Uani 1 1 d . . . C25 C 0.13433(11) 0.86441(8) 0.63835(6) 0.0287(2) Uani 1 1 d . . . H3A H 0.2738(14) 0.5705(8) 0.9979(7) 0.026(3) Uiso 1 1 d . . . H7A H 0.2520(13) 0.3519(8) 0.8573(6) 0.020(3) Uiso 1 1 d . . . H9A H 0.1717(17) 0.7049(11) 1.0088(9) 0.041(4) Uiso 1 1 d . . . H9B H 0.3479(18) 0.7115(11) 1.0075(9) 0.045(4) Uiso 1 1 d . . . H9C H 0.2612(17) 0.7985(10) 0.9860(8) 0.045(4) Uiso 1 1 d . . . H10A H 0.0379(17) 0.7194(10) 0.8842(9) 0.040(4) Uiso 1 1 d . . . H10B H 0.1199(19) 0.8107(13) 0.8660(10) 0.058(5) Uiso 1 1 d . . . H10C H 0.1131(16) 0.7310(10) 0.8029(9) 0.037(4) Uiso 1 1 d . . . H11A H 0.3962(16) 0.7387(10) 0.8048(9) 0.037(4) Uiso 1 1 d . . . H11B H 0.4826(18) 0.7244(11) 0.8805(10) 0.048(4) Uiso 1 1 d . . . H11C H 0.3917(16) 0.8146(11) 0.8673(9) 0.042(4) Uiso 1 1 d . . . H13A H 0.3157(15) 0.2990(9) 0.7436(8) 0.032(3) Uiso 1 1 d . . . H13B H 0.1456(14) 0.3026(9) 0.7544(7) 0.026(3) Uiso 1 1 d . . . H13C H 0.2163(15) 0.3012(9) 0.6682(8) 0.035(3) Uiso 1 1 d . . . H14A H 0.0937(15) 0.5263(9) 0.6740(8) 0.033(3) Uiso 1 1 d . . . H14B H 0.0098(14) 0.4413(9) 0.7087(8) 0.031(3) Uiso 1 1 d . . . H14C H 0.0885(16) 0.4351(10) 0.6243(8) 0.036(4) Uiso 1 1 d . . . H15A H 0.3633(15) 0.4168(9) 0.6180(8) 0.032(3) Uiso 1 1 d . . . H15B H 0.3692(15) 0.5145(10) 0.6561(8) 0.033(3) Uiso 1 1 d . . . H15C H 0.4540(14) 0.4325(9) 0.6928(8) 0.028(3) Uiso 1 1 d . . . H16 H 0.5308(16) 0.7215(9) 0.5391(8) 0.036(4) Uiso 1 1 d . . . H17 H 0.7749(17) 0.6852(10) 0.5074(8) 0.043(4) Uiso 1 1 d . . . H18 H 0.9106(18) 0.6061(10) 0.6029(9) 0.046(4) Uiso 1 1 d . . . H19 H 0.8010(17) 0.5668(11) 0.7213(9) 0.046(4) Uiso 1 1 d . . . H20 H 0.5619(14) 0.6117(9) 0.7435(8) 0.030(3) Uiso 1 1 d . . . H21 H 0.4694(13) 0.8535(8) 0.6638(7) 0.023(3) Uiso 1 1 d . . . H22 H 0.4561(17) 1.0059(10) 0.6288(9) 0.043(4) Uiso 1 1 d . . . H23 H 0.2301(15) 1.0708(9) 0.5977(8) 0.037(3) Uiso 1 1 d . . . H24 H 0.0225(17) 0.9741(10) 0.6076(9) 0.041(4) Uiso 1 1 d . . . H25 H 0.0535(15) 0.8233(9) 0.6405(8) 0.032(3) 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 Li1 0.0282(8) 0.0243(8) 0.0201(7) 0.0009(6) 0.0003(6) 0.0003(6) O1 0.0288(3) 0.0219(3) 0.0174(3) 0.0038(2) 0.0010(3) 0.0011(3) N1 0.0374(4) 0.0231(4) 0.0186(3) -0.0003(3) 0.0012(3) 0.0008(3) N2 0.0256(4) 0.0229(4) 0.0256(4) 0.0011(3) 0.0002(3) -0.0004(3) N3 0.0247(4) 0.0243(3) 0.0215(3) -0.0010(3) 0.0000(3) -0.0007(3) C1 0.0175(3) 0.0207(4) 0.0173(3) 0.0016(3) 0.0004(3) 0.0009(3) C2 0.0201(4) 0.0195(4) 0.0186(3) -0.0003(3) 0.0014(3) 0.0013(3) C3 0.0225(4) 0.0231(4) 0.0168(3) -0.0004(3) 0.0006(3) 0.0013(3) C4 0.0209(4) 0.0221(4) 0.0170(3) 0.0034(3) 0.0000(3) 0.0005(3) C5 0.0191(4) 0.0201(4) 0.0190(3) 0.0011(3) -0.0004(3) 0.0010(3) C6 0.0177(3) 0.0206(4) 0.0177(3) 0.0005(3) -0.0005(3) 0.0005(3) C7 0.0242(4) 0.0219(4) 0.0187(4) -0.0010(3) 0.0007(3) 0.0003(3) C8 0.0361(5) 0.0195(4) 0.0203(4) -0.0007(3) 0.0020(4) 0.0017(4) C9 0.0663(8) 0.0247(5) 0.0231(4) -0.0047(4) 0.0028(6) 0.0026(6) C10 0.0464(7) 0.0295(6) 0.0341(6) 0.0022(5) 0.0043(5) 0.0163(5) C11 0.0464(7) 0.0289(6) 0.0302(5) -0.0021(4) 0.0026(5) -0.0128(5) C12 0.0236(4) 0.0203(4) 0.0174(3) -0.0003(3) -0.0017(3) 0.0009(3) C13 0.0335(5) 0.0217(4) 0.0229(4) -0.0019(3) -0.0034(4) -0.0002(4) C14 0.0249(4) 0.0287(5) 0.0225(4) 0.0011(4) -0.0062(3) -0.0006(4) C15 0.0263(4) 0.0255(5) 0.0200(4) -0.0012(4) 0.0013(3) 0.0025(4) C16 0.0287(5) 0.0275(5) 0.0261(4) 0.0042(4) -0.0003(4) 0.0023(4) C17 0.0316(5) 0.0355(5) 0.0282(4) 0.0037(4) 0.0057(4) 0.0035(4) C18 0.0296(5) 0.0432(6) 0.0377(6) 0.0047(5) 0.0054(4) 0.0107(5) C19 0.0340(5) 0.0398(5) 0.0313(5) 0.0074(4) -0.0018(5) 0.0106(5) C20 0.0304(5) 0.0283(5) 0.0236(4) 0.0014(4) 0.0004(4) 0.0011(4) C21 0.0229(4) 0.0266(5) 0.0290(5) -0.0026(4) -0.0024(4) 0.0004(4) C22 0.0235(4) 0.0255(5) 0.0369(5) -0.0027(4) 0.0014(4) -0.0031(4) C23 0.0300(5) 0.0246(4) 0.0354(5) 0.0031(4) 0.0018(4) 0.0030(4) C24 0.0227(4) 0.0342(6) 0.0387(5) 0.0041(5) 0.0000(4) 0.0045(4) C25 0.0225(4) 0.0306(5) 0.0329(5) 0.0017(4) 0.0024(4) -0.0035(4) _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 O1 1.8223(17) . ? Li1 N1 2.0781(18) 2_564 ? Li1 N3 2.1244(19) . ? Li1 N2 2.1469(19) . ? O1 C1 1.2812(10) . ? N1 C7 1.1529(12) . ? N1 Li1 2.0781(18) 2_565 ? N2 C16 1.3412(13) . ? N2 C20 1.3425(13) . ? N3 C25 1.3409(13) . ? N3 C21 1.3410(13) . ? C1 C6 1.4551(11) . ? C1 C2 1.4555(11) . ? C2 C3 1.3817(12) . ? C2 C8 1.5336(12) . ? C3 C4 1.4034(12) . ? C3 H3A 0.969(12) . ? C4 C5 1.4057(11) . ? C4 C7 1.4263(12) . ? C5 C6 1.3808(11) . ? C5 H7A 0.969(11) . ? C6 C12 1.5398(11) . ? C8 C10 1.5351(16) . ? C8 C11 1.5369(16) . ? C8 C9 1.5399(13) . ? C9 H9A 1.025(16) . ? C9 H9B 1.000(17) . ? C9 H9C 1.000(15) . ? C10 H10A 0.977(16) . ? C10 H10B 0.988(19) . ? C10 H10C 0.990(15) . ? C11 H11A 0.942(15) . ? C11 H11B 0.985(17) . ? C11 H11C 0.991(16) . ? C12 C13 1.5380(13) . ? C12 C14 1.5395(13) . ? C12 C15 1.5400(13) . ? C13 H13A 0.984(14) . ? C13 H13B 0.999(13) . ? C13 H13C 0.991(14) . ? C14 H14A 0.988(14) . ? C14 H14B 0.985(14) . ? C14 H14C 1.024(14) . ? C15 H15A 0.993(14) . ? C15 H15B 0.974(14) . ? C15 H15C 0.967(13) . ? C16 C17 1.3842(15) . ? C16 H16 0.977(15) . ? C17 C18 1.3824(16) . ? C17 H17 1.013(14) . ? C18 C19 1.3859(16) . ? C18 H18 0.956(17) . ? C19 C20 1.3838(15) . ? C19 H19 0.962(16) . ? C20 H20 0.951(14) . ? C21 C22 1.3854(15) . ? C21 H21 0.976(12) . ? C22 C23 1.3875(15) . ? C22 H22 0.947(16) . ? C23 C24 1.3821(16) . ? C23 H23 0.982(13) . ? C24 C25 1.3855(16) . ? C24 H24 0.938(16) . ? C25 H25 0.969(14) . ? 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 O1 Li1 N1 115.18(9) . 2_564 ? O1 Li1 N3 126.31(9) . . ? N1 Li1 N3 99.95(7) 2_564 . ? O1 Li1 N2 106.09(8) . . ? N1 Li1 N2 100.50(7) 2_564 . ? N3 Li1 N2 105.72(8) . . ? C1 O1 Li1 167.42(9) . . ? C7 N1 Li1 151.44(9) . 2_565 ? C16 N2 C20 117.02(9) . . ? C16 N2 Li1 123.06(8) . . ? C20 N2 Li1 119.26(8) . . ? C25 N3 C21 116.65(8) . . ? C25 N3 Li1 124.59(8) . . ? C21 N3 Li1 117.65(8) . . ? O1 C1 C6 121.01(7) . . ? O1 C1 C2 120.79(7) . . ? C6 C1 C2 118.20(7) . . ? C3 C2 C1 119.34(8) . . ? C3 C2 C8 120.53(7) . . ? C1 C2 C8 120.13(7) . . ? C2 C3 C4 121.77(8) . . ? C2 C3 H3A 121.0(7) . . ? C4 C3 H3A 117.2(7) . . ? C3 C4 C5 119.46(7) . . ? C3 C4 C7 119.35(8) . . ? C5 C4 C7 121.19(8) . . ? C6 C5 C4 121.71(8) . . ? C6 C5 H7A 118.8(6) . . ? C4 C5 H7A 119.5(6) . . ? C5 C6 C1 119.40(7) . . ? C5 C6 C12 120.73(7) . . ? C1 C6 C12 119.87(7) . . ? N1 C7 C4 178.51(10) . . ? C2 C8 C10 109.80(9) . . ? C2 C8 C11 110.59(8) . . ? C10 C8 C11 110.08(9) . . ? C2 C8 C9 112.02(7) . . ? C10 C8 C9 107.23(10) . . ? C11 C8 C9 107.03(10) . . ? C8 C9 H9A 111.6(9) . . ? C8 C9 H9B 112.0(9) . . ? H9A C9 H9B 107.9(11) . . ? C8 C9 H9C 110.1(8) . . ? H9A C9 H9C 111.3(13) . . ? H9B C9 H9C 103.6(14) . . ? C8 C10 H10A 108.8(9) . . ? C8 C10 H10B 109.8(11) . . ? H10A C10 H10B 108.4(14) . . ? C8 C10 H10C 112.5(9) . . ? H10A C10 H10C 107.3(12) . . ? H10B C10 H10C 109.9(13) . . ? C8 C11 H11A 111.1(9) . . ? C8 C11 H11B 111.4(10) . . ? H11A C11 H11B 107.4(14) . . ? C8 C11 H11C 109.8(9) . . ? H11A C11 H11C 108.5(12) . . ? H11B C11 H11C 108.6(13) . . ? C13 C12 C14 107.73(8) . . ? C13 C12 C6 111.96(7) . . ? C14 C12 C6 109.48(7) . . ? C13 C12 C15 106.98(8) . . ? C14 C12 C15 110.24(7) . . ? C6 C12 C15 110.40(7) . . ? C12 C13 H13A 111.0(8) . . ? C12 C13 H13B 112.5(8) . . ? H13A C13 H13B 106.6(10) . . ? C12 C13 H13C 107.9(8) . . ? H13A C13 H13C 108.2(11) . . ? H13B C13 H13C 110.4(11) . . ? C12 C14 H14A 111.9(8) . . ? C12 C14 H14B 110.7(8) . . ? H14A C14 H14B 109.0(11) . . ? C12 C14 H14C 109.3(8) . . ? H14A C14 H14C 106.6(11) . . ? H14B C14 H14C 109.2(11) . . ? C12 C15 H15A 110.5(8) . . ? C12 C15 H15B 111.2(8) . . ? H15A C15 H15B 109.2(12) . . ? C12 C15 H15C 110.2(8) . . ? H15A C15 H15C 105.9(11) . . ? H15B C15 H15C 109.9(12) . . ? N2 C16 C17 123.54(9) . . ? N2 C16 H16 115.7(9) . . ? C17 C16 H16 120.8(9) . . ? C18 C17 C16 118.66(10) . . ? C18 C17 H17 121.2(9) . . ? C16 C17 H17 120.1(9) . . ? C17 C18 C19 118.68(10) . . ? C17 C18 H18 120.5(10) . . ? C19 C18 H18 120.9(10) . . ? C20 C19 C18 118.82(10) . . ? C20 C19 H19 120.6(9) . . ? C18 C19 H19 120.5(9) . . ? N2 C20 C19 123.28(10) . . ? N2 C20 H20 116.8(8) . . ? C19 C20 H20 119.9(8) . . ? N3 C21 C22 123.84(9) . . ? N3 C21 H21 114.8(7) . . ? C22 C21 H21 121.4(7) . . ? C21 C22 C23 118.35(9) . . ? C21 C22 H22 119.4(9) . . ? C23 C22 H22 122.2(9) . . ? C24 C23 C22 118.84(9) . . ? C24 C23 H23 122.0(9) . . ? C22 C23 H23 119.1(9) . . ? C23 C24 C25 118.59(10) . . ? C23 C24 H24 122.8(9) . . ? C25 C24 H24 118.6(9) . . ? N3 C25 C24 123.72(10) . . ? N3 C25 H25 114.8(8) . . ? C24 C25 H25 121.5(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Li1 O1 C1 122.0(3) 2_564 . . . ? N3 Li1 O1 C1 -112.4(3) . . . . ? N2 Li1 O1 C1 11.8(4) . . . . ? O1 Li1 N2 C16 160.66(9) . . . . ? N1 Li1 N2 C16 40.42(12) 2_564 . . . ? N3 Li1 N2 C16 -63.16(11) . . . . ? O1 Li1 N2 C20 -9.75(12) . . . . ? N1 Li1 N2 C20 -129.99(9) 2_564 . . . ? N3 Li1 N2 C20 126.43(9) . . . . ? O1 Li1 N3 C25 -78.29(14) . . . . ? N1 Li1 N3 C25 53.38(11) 2_564 . . . ? N2 Li1 N3 C25 157.36(8) . . . . ? O1 Li1 N3 C21 114.16(12) . . . . ? N1 Li1 N3 C21 -114.17(9) 2_564 . . . ? N2 Li1 N3 C21 -10.19(11) . . . . ? Li1 O1 C1 C6 -92.7(4) . . . . ? Li1 O1 C1 C2 87.4(4) . . . . ? O1 C1 C2 C3 -176.43(9) . . . . ? C6 C1 C2 C3 3.68(12) . . . . ? O1 C1 C2 C8 3.74(13) . . . . ? C6 C1 C2 C8 -176.16(9) . . . . ? C1 C2 C3 C4 -1.32(13) . . . . ? C8 C2 C3 C4 178.51(9) . . . . ? C2 C3 C4 C5 -1.58(14) . . . . ? C2 C3 C4 C7 179.59(8) . . . . ? C3 C4 C5 C6 2.08(14) . . . . ? C7 C4 C5 C6 -179.12(9) . . . . ? C4 C5 C6 C1 0.37(14) . . . . ? C4 C5 C6 C12 -179.30(8) . . . . ? O1 C1 C6 C5 176.90(8) . . . . ? C2 C1 C6 C5 -3.21(13) . . . . ? O1 C1 C6 C12 -3.43(13) . . . . ? C2 C1 C6 C12 176.47(8) . . . . ? Li1 N1 C7 C4 55(4) 2_565 . . . ? C3 C4 C7 N1 8(4) . . . . ? C5 C4 C7 N1 -171(4) . . . . ? C3 C2 C8 C10 -121.48(10) . . . . ? C1 C2 C8 C10 58.35(12) . . . . ? C3 C2 C8 C11 116.84(10) . . . . ? C1 C2 C8 C11 -63.33(12) . . . . ? C3 C2 C8 C9 -2.45(15) . . . . ? C1 C2 C8 C9 177.38(10) . . . . ? C5 C6 C12 C13 0.62(12) . . . . ? C1 C6 C12 C13 -179.05(8) . . . . ? C5 C6 C12 C14 120.01(9) . . . . ? C1 C6 C12 C14 -59.65(11) . . . . ? C5 C6 C12 C15 -118.45(9) . . . . ? C1 C6 C12 C15 61.88(10) . . . . ? C20 N2 C16 C17 -0.36(16) . . . . ? Li1 N2 C16 C17 -170.97(10) . . . . ? N2 C16 C17 C18 0.03(17) . . . . ? C16 C17 C18 C19 0.16(18) . . . . ? C17 C18 C19 C20 0.00(18) . . . . ? C16 N2 C20 C19 0.53(15) . . . . ? Li1 N2 C20 C19 171.52(10) . . . . ? C18 C19 C20 N2 -0.36(18) . . . . ? C25 N3 C21 C22 -0.92(14) . . . . ? Li1 N3 C21 C22 167.63(10) . . . . ? N3 C21 C22 C23 0.75(16) . . . . ? C21 C22 C23 C24 0.16(16) . . . . ? C22 C23 C24 C25 -0.83(16) . . . . ? C21 N3 C25 C24 0.19(15) . . . . ? Li1 N3 C25 C24 -167.48(10) . . . . ? C23 C24 C25 N3 0.68(17) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 30.06 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.232 _refine_diff_density_min -0.139 _refine_diff_density_rms 0.027 # Attachment '3b.cif' data_kengone _database_code_depnum_ccdc_archive 'CCDC 287372' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'lithium 2,6-di-t-butyl-4-cyanophenoxide THF' _chemical_melting_point ? _chemical_formula_moiety 'C23 H36 Li N O3' _chemical_formula_sum 'C23 H36 Li N O3' _chemical_formula_weight 381.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Li Li -0.0003 0.0001 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _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 11.9150(2) _cell_length_b 14.8575(2) _cell_length_c 12.5174(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.759(1) _cell_angle_gamma 90.00 _cell_volume 2214.88(7) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5217 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description cube _exptl_crystal_colour 'clear colorless' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.144 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type none _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 'Nonius Kappa CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8960 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 27.51 _reflns_number_total 5088 _reflns_number_gt 3564 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Denzo & Collect' _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0513P)^2^+0.6231P] 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 5088 _refine_ls_number_parameters 382 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0795 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1161 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 Li1 Li 1.0581(2) 0.25692(16) 0.46297(19) 0.0242(5) Uani 1 1 d . . . O1 O 1.08837(8) 0.15811(6) 0.38483(7) 0.0214(2) Uani 1 1 d . . . O2 O 0.92017(9) 0.33264(7) 0.42218(9) 0.0334(3) Uani 1 1 d . . . O3 O 1.03735(9) 0.24628(7) 0.61946(8) 0.0300(3) Uani 1 1 d . . . N1 N 1.32322(10) -0.14358(8) 0.06356(10) 0.0250(3) Uani 1 1 d . . . C1 C 1.13127(11) 0.09920(9) 0.32321(11) 0.0175(3) Uani 1 1 d . . . C2 C 1.21275(11) 0.03420(9) 0.36432(11) 0.0174(3) Uani 1 1 d . . . C3 C 1.10010(11) 0.09646(9) 0.21002(11) 0.0179(3) Uani 1 1 d . . . C4 C 1.14994(12) 0.03413(9) 0.14517(11) 0.0192(3) Uani 1 1 d . . . C5 C 1.22965(11) -0.02772(9) 0.18565(11) 0.0195(3) Uani 1 1 d . . . C6 C 1.25904(11) -0.02658(9) 0.29490(11) 0.0191(3) Uani 1 1 d . . . C7 C 1.28005(11) -0.09174(10) 0.11708(11) 0.0205(3) Uani 1 1 d . . . C8 C 1.24699(12) 0.03374(9) 0.48391(11) 0.0203(3) Uani 1 1 d . . . C9 C 1.14399(13) 0.01944(11) 0.55242(12) 0.0242(3) Uani 1 1 d . . . C10 C 1.30468(13) 0.12319(11) 0.51459(13) 0.0244(3) Uani 1 1 d . . . C11 C 1.33069(14) -0.04201(11) 0.51160(13) 0.0284(4) Uani 1 1 d . . . C12 C 1.01423(11) 0.16406(9) 0.16308(11) 0.0192(3) Uani 1 1 d . . . C13 C 1.06158(14) 0.25960(10) 0.17459(13) 0.0252(3) Uani 1 1 d . . . C14 C 0.90229(13) 0.15539(12) 0.21969(14) 0.0282(4) Uani 1 1 d . . . C15 C 0.98885(15) 0.14850(12) 0.04367(13) 0.0292(4) Uani 1 1 d . . . C16 C 0.80368(14) 0.30786(13) 0.42801(14) 0.0352(4) Uani 1 1 d . A . C17 C 0.74361(15) 0.36369(13) 0.34276(14) 0.0349(4) Uani 1 1 d . . . C18 C 0.80982(15) 0.45113(12) 0.34706(15) 0.0362(4) Uani 1 1 d . A . C19 C 0.9299(2) 0.42053(16) 0.3661(3) 0.0270(7) Uani 0.709(7) 1 d P A 1 H19A H 0.9682 0.4131 0.2976 0.032 Uiso 0.709(7) 1 calc PR A 1 H19B H 0.9723 0.4644 0.4110 0.032 Uiso 0.709(7) 1 calc PR A 1 C20 C 0.94733(15) 0.19749(12) 0.66871(14) 0.0314(4) Uani 1 1 d . A . C21 C 0.89626(15) 0.26171(13) 0.74646(15) 0.0433(5) Uani 1 1 d . . . H21A H 0.8336 0.2957 0.7119 0.052 Uiso 1 1 d R A . H21B H 0.8679 0.2291 0.8091 0.052 Uiso 1 1 d R . . C22 C 0.9898(2) 0.32516(19) 0.7763(2) 0.0356(9) Uani 0.709(7) 1 d P A 1 H22A H 1.0356 0.2997 0.8363 0.043 Uiso 0.709(7) 1 d PR A 1 H22B H 0.9619 0.3853 0.7968 0.043 Uiso 0.709(7) 1 d PR A 1 C23 C 1.05790(18) 0.32840(13) 0.67813(15) 0.0386(4) Uani 1 1 d . A . C19A C 0.9142(9) 0.4210(7) 0.4083(9) 0.055(3) Uiso 0.291(7) 1 d P A 2 H19C H 0.9809 0.4412 0.3696 0.066 Uiso 0.291(7) 1 calc PR A 2 H19D H 0.9165 0.4506 0.4792 0.066 Uiso 0.291(7) 1 calc PR A 2 C22A C 0.9510(6) 0.3473(4) 0.7265(6) 0.0304(19) Uiso 0.291(7) 1 d P A 2 H22C H 0.9634 0.3805 0.7945 0.036 Uiso 0.291(7) 1 calc PR A 2 H22D H 0.9034 0.3846 0.6779 0.036 Uiso 0.291(7) 1 calc PR A 2 H4 H 1.1316(12) 0.0326(10) 0.0686(12) 0.019(4) Uiso 1 1 d . . . H6 H 1.3163(12) -0.0711(10) 0.3209(11) 0.020(4) Uiso 1 1 d . . . H9A H 1.1661(14) 0.0218(11) 0.6293(14) 0.037(5) Uiso 1 1 d . . . H9B H 1.1064(14) -0.0387(12) 0.5368(13) 0.032(4) Uiso 1 1 d . . . H9C H 1.0865(14) 0.0674(12) 0.5398(13) 0.035(5) Uiso 1 1 d . . . H10A H 1.2574(13) 0.1750(11) 0.4980(12) 0.027(4) Uiso 1 1 d . . . H10B H 1.3241(13) 0.1243(11) 0.5934(14) 0.029(4) Uiso 1 1 d . . . H10C H 1.3764(15) 0.1299(11) 0.4764(13) 0.034(4) Uiso 1 1 d . . . H11A H 1.3488(14) -0.0416(11) 0.5895(15) 0.034(5) Uiso 1 1 d . . . H11B H 1.4042(15) -0.0350(11) 0.4731(14) 0.034(5) Uiso 1 1 d . . . H11C H 1.2982(14) -0.1042(12) 0.4945(13) 0.034(4) Uiso 1 1 d . . . H13A H 1.0809(14) 0.2749(11) 0.2486(14) 0.035(5) Uiso 1 1 d . . . H13B H 1.0090(13) 0.3022(11) 0.1457(13) 0.029(4) Uiso 1 1 d . . . H13C H 1.1316(15) 0.2669(11) 0.1333(13) 0.033(4) Uiso 1 1 d . . . H14A H 0.8716(15) 0.0939(13) 0.2090(14) 0.045(5) Uiso 1 1 d . . . H14B H 0.9111(13) 0.1651(11) 0.2984(14) 0.028(4) Uiso 1 1 d . . . H14C H 0.8479(14) 0.1987(12) 0.1900(13) 0.030(4) Uiso 1 1 d . . . H15A H 0.9599(15) 0.0872(13) 0.0302(14) 0.040(5) Uiso 1 1 d . . . H15B H 0.9312(15) 0.1935(12) 0.0170(14) 0.040(5) Uiso 1 1 d . . . H15C H 1.0574(15) 0.1593(11) -0.0016(14) 0.038(5) Uiso 1 1 d . . . H16A H 0.7783(15) 0.3259(12) 0.4988(15) 0.044(5) Uiso 1 1 d . . . H16B H 0.7979(14) 0.2418(13) 0.4188(14) 0.038(5) Uiso 1 1 d . . . H17A H 0.7485(14) 0.3329(12) 0.2747(15) 0.039(5) Uiso 1 1 d . . . H17B H 0.6627(16) 0.3713(12) 0.3582(14) 0.044(5) Uiso 1 1 d . . . H18A H 0.8054(15) 0.4852(13) 0.2784(15) 0.047(5) Uiso 1 1 d . . . H18B H 0.7824(18) 0.4926(15) 0.4076(18) 0.066(6) Uiso 1 1 d . . . H20A H 0.8954(15) 0.1766(12) 0.6109(15) 0.040(5) Uiso 1 1 d . . . H20B H 0.9810(15) 0.1432(13) 0.7052(15) 0.047(5) Uiso 1 1 d . . . H23A H 1.033(2) 0.3796(18) 0.631(2) 0.095(9) Uiso 1 1 d . . . H23B H 1.137(2) 0.3328(16) 0.697(2) 0.083(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 Li1 0.0283(13) 0.0185(12) 0.0260(13) -0.0011(10) 0.0051(10) -0.0009(10) O1 0.0254(5) 0.0187(5) 0.0202(5) -0.0037(4) 0.0017(4) 0.0032(4) O2 0.0300(6) 0.0246(6) 0.0457(7) 0.0010(5) 0.0011(5) 0.0056(5) O3 0.0403(6) 0.0245(6) 0.0259(6) -0.0046(5) 0.0133(5) -0.0083(5) N1 0.0284(7) 0.0239(7) 0.0226(6) -0.0003(5) 0.0018(5) 0.0052(6) C1 0.0170(7) 0.0157(7) 0.0199(7) -0.0013(6) 0.0026(5) -0.0028(5) C2 0.0174(7) 0.0161(7) 0.0189(7) 0.0006(6) 0.0003(5) -0.0037(5) C3 0.0176(7) 0.0160(7) 0.0201(7) -0.0002(6) 0.0001(5) -0.0017(6) C4 0.0211(7) 0.0192(7) 0.0171(7) -0.0003(6) -0.0014(6) -0.0022(6) C5 0.0209(7) 0.0164(7) 0.0214(7) -0.0028(6) 0.0028(6) 0.0006(6) C6 0.0186(7) 0.0167(7) 0.0220(7) 0.0016(6) 0.0006(6) 0.0006(6) C7 0.0214(7) 0.0199(7) 0.0201(7) 0.0027(6) -0.0006(6) 0.0004(6) C8 0.0209(7) 0.0207(7) 0.0191(7) -0.0001(6) -0.0017(6) -0.0012(6) C9 0.0262(8) 0.0260(8) 0.0203(8) 0.0022(7) 0.0011(6) -0.0042(7) C10 0.0235(8) 0.0272(9) 0.0224(8) -0.0025(7) -0.0015(6) -0.0046(7) C11 0.0319(9) 0.0304(9) 0.0226(8) 0.0007(7) -0.0049(7) 0.0060(7) C12 0.0200(7) 0.0186(7) 0.0189(7) -0.0007(6) -0.0020(6) 0.0017(6) C13 0.0279(9) 0.0196(8) 0.0276(8) 0.0036(7) -0.0051(7) 0.0002(7) C14 0.0198(8) 0.0299(9) 0.0347(9) 0.0028(8) -0.0008(7) 0.0011(7) C15 0.0329(9) 0.0295(9) 0.0246(8) -0.0038(7) -0.0077(7) 0.0100(8) C16 0.0302(9) 0.0436(11) 0.0322(9) 0.0036(8) 0.0082(7) 0.0050(8) C17 0.0292(9) 0.0474(11) 0.0280(9) 0.0020(8) 0.0019(7) 0.0008(8) C18 0.0420(10) 0.0353(10) 0.0310(9) -0.0003(8) -0.0055(8) 0.0077(8) C19 0.0311(14) 0.0154(12) 0.0346(16) 0.0056(11) 0.0004(12) 0.0028(9) C20 0.0367(9) 0.0294(9) 0.0286(9) 0.0008(7) 0.0070(7) -0.0091(8) C21 0.0402(10) 0.0492(11) 0.0414(10) -0.0117(9) 0.0171(8) -0.0113(9) C22 0.0391(15) 0.0388(15) 0.0291(16) -0.0081(12) 0.0061(12) -0.0046(12) C23 0.0476(11) 0.0341(10) 0.0350(10) -0.0140(8) 0.0142(9) -0.0128(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 Li1 O1 1.806(3) . ? Li1 O3 1.988(3) . ? Li1 O2 2.044(3) . ? Li1 N1 2.079(3) 2_755 ? O1 C1 1.2832(16) . ? O2 C19A 1.326(11) . ? O2 C16 1.440(2) . ? O2 C19 1.489(3) . ? O3 C23 1.4413(19) . ? O3 C20 1.4479(19) . ? N1 C7 1.1523(18) . ? N1 Li1 2.079(3) 2_745 ? C1 C2 1.4523(19) . ? C1 C3 1.4542(18) . ? C2 C6 1.380(2) . ? C2 C8 1.5394(19) . ? C3 C4 1.3780(19) . ? C3 C12 1.5375(19) . ? C4 C5 1.4049(19) . ? C4 H4 0.976(15) . ? C5 C6 1.4013(19) . ? C5 C7 1.426(2) . ? C6 H6 0.997(15) . ? C8 C9 1.533(2) . ? C8 C11 1.536(2) . ? C8 C10 1.539(2) . ? C9 H9A 0.991(18) . ? C9 H9B 0.990(18) . ? C9 H9C 0.997(18) . ? C10 H10A 0.973(17) . ? C10 H10B 1.006(17) . ? C10 H10C 0.997(17) . ? C11 H11A 0.992(18) . ? C11 H11B 1.018(18) . ? C11 H11C 1.021(17) . ? C12 C13 1.533(2) . ? C12 C15 1.533(2) . ? C12 C14 1.535(2) . ? C13 H13A 0.974(18) . ? C13 H13B 0.954(17) . ? C13 H13C 1.001(18) . ? C14 H14A 0.992(19) . ? C14 H14B 0.998(17) . ? C14 H14C 0.978(17) . ? C15 H15A 0.986(19) . ? C15 H15B 1.008(18) . ? C15 H15C 1.020(18) . ? C16 C17 1.514(2) . ? C16 H16A 0.983(19) . ? C16 H16B 0.991(18) . ? C17 C18 1.520(3) . ? C17 H17A 0.970(19) . ? C17 H17B 0.995(18) . ? C18 C19A 1.509(10) . ? C18 C19 1.513(3) . ? C18 H18A 0.997(19) . ? C18 H18B 1.04(2) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.505(2) . ? C20 H20A 0.987(19) . ? C20 H20B 1.005(19) . ? C21 C22A 1.454(6) . ? C21 C22 1.498(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.494(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C22A 1.455(6) . ? C23 H23A 1.00(3) . ? C23 H23B 0.97(3) . ? C19A H19C 0.9900 . ? C19A H19D 0.9900 . ? C22A H22B 1.0496 . ? C22A H22C 0.9900 . ? C22A H22D 0.9900 . ? 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 O1 Li1 O3 120.12(13) . . ? O1 Li1 O2 118.97(13) . . ? O3 Li1 O2 99.58(11) . . ? O1 Li1 N1 110.08(13) . 2_755 ? O3 Li1 N1 108.65(12) . 2_755 ? O2 Li1 N1 96.56(11) . 2_755 ? C1 O1 Li1 165.83(12) . . ? C19A O2 C16 102.2(5) . . ? C19A O2 C19 22.3(5) . . ? C16 O2 C19 109.69(14) . . ? C19A O2 Li1 128.1(4) . . ? C16 O2 Li1 128.00(12) . . ? C19 O2 Li1 121.82(14) . . ? C23 O3 C20 108.86(12) . . ? C23 O3 Li1 114.23(12) . . ? C20 O3 Li1 125.14(12) . . ? C7 N1 Li1 152.37(13) . 2_745 ? O1 C1 C2 120.99(12) . . ? O1 C1 C3 120.68(12) . . ? C2 C1 C3 118.33(12) . . ? C6 C2 C1 119.20(12) . . ? C6 C2 C8 120.68(12) . . ? C1 C2 C8 120.12(12) . . ? C4 C3 C1 119.41(12) . . ? C4 C3 C12 120.50(12) . . ? C1 C3 C12 120.07(12) . . ? C3 C4 C5 121.73(13) . . ? C3 C4 H4 120.4(8) . . ? C5 C4 H4 117.8(8) . . ? C6 C5 C4 119.34(12) . . ? C6 C5 C7 119.88(13) . . ? C4 C5 C7 120.78(13) . . ? C2 C6 C5 121.99(13) . . ? C2 C6 H6 120.8(8) . . ? C5 C6 H6 117.3(8) . . ? N1 C7 C5 178.16(15) . . ? C9 C8 C11 107.30(12) . . ? C9 C8 C2 110.59(11) . . ? C11 C8 C2 111.93(12) . . ? C9 C8 C10 109.82(12) . . ? C11 C8 C10 107.12(12) . . ? C2 C8 C10 109.98(11) . . ? C8 C9 H9A 110.2(10) . . ? C8 C9 H9B 112.0(10) . . ? H9A C9 H9B 109.1(14) . . ? C8 C9 H9C 111.7(10) . . ? H9A C9 H9C 106.8(14) . . ? H9B C9 H9C 106.8(13) . . ? C8 C10 H10A 112.3(9) . . ? C8 C10 H10B 110.3(9) . . ? H10A C10 H10B 108.0(13) . . ? C8 C10 H10C 110.4(10) . . ? H10A C10 H10C 108.5(13) . . ? H10B C10 H10C 107.1(13) . . ? C8 C11 H11A 109.7(10) . . ? C8 C11 H11B 112.3(9) . . ? H11A C11 H11B 107.5(13) . . ? C8 C11 H11C 112.1(9) . . ? H11A C11 H11C 106.3(13) . . ? H11B C11 H11C 108.6(13) . . ? C13 C12 C15 106.99(12) . . ? C13 C12 C14 110.91(12) . . ? C15 C12 C14 106.81(12) . . ? C13 C12 C3 109.30(11) . . ? C15 C12 C3 112.53(12) . . ? C14 C12 C3 110.26(12) . . ? C12 C13 H13A 112.4(10) . . ? C12 C13 H13B 110.0(10) . . ? H13A C13 H13B 109.9(14) . . ? C12 C13 H13C 111.2(10) . . ? H13A C13 H13C 106.8(13) . . ? H13B C13 H13C 106.3(13) . . ? C12 C14 H14A 109.7(10) . . ? C12 C14 H14B 112.1(9) . . ? H14A C14 H14B 107.1(14) . . ? C12 C14 H14C 110.1(10) . . ? H14A C14 H14C 108.5(14) . . ? H14B C14 H14C 109.2(13) . . ? C12 C15 H15A 111.3(10) . . ? C12 C15 H15B 109.6(10) . . ? H15A C15 H15B 108.9(14) . . ? C12 C15 H15C 112.4(10) . . ? H15A C15 H15C 109.4(14) . . ? H15B C15 H15C 105.1(14) . . ? O2 C16 C17 105.06(13) . . ? O2 C16 H16A 107.4(11) . . ? C17 C16 H16A 109.6(11) . . ? O2 C16 H16B 108.1(10) . . ? C17 C16 H16B 115.6(10) . . ? H16A C16 H16B 110.7(15) . . ? C16 C17 C18 102.10(14) . . ? C16 C17 H17A 108.8(11) . . ? C18 C17 H17A 112.9(11) . . ? C16 C17 H17B 111.4(10) . . ? C18 C17 H17B 113.6(11) . . ? H17A C17 H17B 107.9(15) . . ? C19A C18 C19 21.6(4) . . ? C19A C18 C17 100.6(4) . . ? C19 C18 C17 103.64(16) . . ? C19A C18 H18A 127.5(11) . . ? C19 C18 H18A 108.2(11) . . ? C17 C18 H18A 112.9(11) . . ? C19A C18 H18B 94.5(13) . . ? C19 C18 H18B 112.4(12) . . ? C17 C18 H18B 111.1(12) . . ? H18A C18 H18B 108.6(16) . . ? O2 C19 C18 104.55(19) . . ? O2 C19 H19A 110.8 . . ? C18 C19 H19A 110.8 . . ? O2 C19 H19B 110.8 . . ? C18 C19 H19B 110.8 . . ? H19A C19 H19B 108.9 . . ? O3 C20 C21 106.12(13) . . ? O3 C20 H20A 107.5(10) . . ? C21 C20 H20A 114.6(10) . . ? O3 C20 H20B 107.8(10) . . ? C21 C20 H20B 112.2(10) . . ? H20A C20 H20B 108.2(15) . . ? C22A C21 C22 32.7(3) . . ? C22A C21 C20 104.5(3) . . ? C22 C21 C20 104.33(15) . . ? C22A C21 H21A 79.3 . . ? C22 C21 H21A 109.4 . . ? C20 C21 H21A 110.8 . . ? C22A C21 H21B 136.8 . . ? C22 C21 H21B 112.3 . . ? C20 C21 H21B 110.9 . . ? H21A C21 H21B 109.0 . . ? C23 C22 C21 103.56(18) . . ? C23 C22 H22A 109.6 . . ? C21 C22 H22A 109.7 . . ? C23 C22 H22B 112.3 . . ? C21 C22 H22B 112.3 . . ? H22A C22 H22B 109.2 . . ? O3 C23 C22A 103.8(3) . . ? O3 C23 C22 107.67(15) . . ? C22A C23 C22 32.7(3) . . ? O3 C23 H23A 107.3(15) . . ? C22A C23 H23A 81.3(15) . . ? C22 C23 H23A 110.4(15) . . ? O3 C23 H23B 109.5(15) . . ? C22A C23 H23B 137.9(15) . . ? C22 C23 H23B 110.3(15) . . ? H23A C23 H23B 112(2) . . ? O2 C19A C18 113.6(7) . . ? O2 C19A H19C 108.9 . . ? C18 C19A H19C 108.9 . . ? O2 C19A H19D 108.9 . . ? C18 C19A H19D 108.9 . . ? H19C C19A H19D 107.7 . . ? C21 C22A C23 107.8(4) . . ? C21 C22A H22B 111.8 . . ? C23 C22A H22B 111.4 . . ? C21 C22A H22C 110.1 . . ? C23 C22A H22C 110.1 . . ? H22B C22A H22C 3.0 . . ? C21 C22A H22D 110.1 . . ? C23 C22A H22D 110.1 . . ? H22B C22A H22D 105.5 . . ? H22C C22A H22D 108.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Li1 O1 C1 -123.0(5) . . . . ? O2 Li1 O1 C1 114.2(5) . . . . ? N1 Li1 O1 C1 4.3(6) 2_755 . . . ? O1 Li1 O2 C19A -130.4(7) . . . . ? O3 Li1 O2 C19A 97.2(7) . . . . ? N1 Li1 O2 C19A -13.1(7) 2_755 . . . ? O1 Li1 O2 C16 67.0(2) . . . . ? O3 Li1 O2 C16 -65.51(17) . . . . ? N1 Li1 O2 C16 -175.74(13) 2_755 . . . ? O1 Li1 O2 C19 -104.2(2) . . . . ? O3 Li1 O2 C19 123.33(19) . . . . ? N1 Li1 O2 C19 13.1(2) 2_755 . . . ? O1 Li1 O3 C23 156.69(16) . . . . ? O2 Li1 O3 C23 -71.57(16) . . . . ? N1 Li1 O3 C23 28.76(18) 2_755 . . . ? O1 Li1 O3 C20 -64.7(2) . . . . ? O2 Li1 O3 C20 67.05(16) . . . . ? N1 Li1 O3 C20 167.38(13) 2_755 . . . ? Li1 O1 C1 C2 87.7(5) . . . . ? Li1 O1 C1 C3 -91.7(5) . . . . ? O1 C1 C2 C6 -178.37(12) . . . . ? C3 C1 C2 C6 1.09(19) . . . . ? O1 C1 C2 C8 1.40(19) . . . . ? C3 C1 C2 C8 -179.14(12) . . . . ? O1 C1 C3 C4 178.14(12) . . . . ? C2 C1 C3 C4 -1.32(19) . . . . ? O1 C1 C3 C12 -0.49(19) . . . . ? C2 C1 C3 C12 -179.95(12) . . . . ? C1 C3 C4 C5 0.6(2) . . . . ? C12 C3 C4 C5 179.23(12) . . . . ? C3 C4 C5 C6 0.4(2) . . . . ? C3 C4 C5 C7 179.91(13) . . . . ? C1 C2 C6 C5 -0.1(2) . . . . ? C8 C2 C6 C5 -179.91(12) . . . . ? C4 C5 C6 C2 -0.6(2) . . . . ? C7 C5 C6 C2 179.85(13) . . . . ? Li1 N1 C7 C5 17(5) 2_745 . . . ? C6 C5 C7 N1 -25(5) . . . . ? C4 C5 C7 N1 155(5) . . . . ? C6 C2 C8 C9 -121.80(14) . . . . ? C1 C2 C8 C9 58.43(16) . . . . ? C6 C2 C8 C11 -2.22(18) . . . . ? C1 C2 C8 C11 178.02(12) . . . . ? C6 C2 C8 C10 116.74(14) . . . . ? C1 C2 C8 C10 -63.03(16) . . . . ? C4 C3 C12 C13 -115.19(14) . . . . ? C1 C3 C12 C13 63.43(16) . . . . ? C4 C3 C12 C15 3.52(18) . . . . ? C1 C3 C12 C15 -177.86(13) . . . . ? C4 C3 C12 C14 122.66(14) . . . . ? C1 C3 C12 C14 -58.73(16) . . . . ? C19A O2 C16 C17 41.0(5) . . . . ? C19 O2 C16 C17 19.2(2) . . . . ? Li1 O2 C16 C17 -152.83(14) . . . . ? O2 C16 C17 C18 -35.23(18) . . . . ? C16 C17 C18 C19A 16.1(5) . . . . ? C16 C17 C18 C19 37.9(2) . . . . ? C19A O2 C19 C18 -68.9(13) . . . . ? C16 O2 C19 C18 4.9(3) . . . . ? Li1 O2 C19 C18 177.48(15) . . . . ? C19A C18 C19 O2 57.5(12) . . . . ? C17 C18 C19 O2 -26.8(3) . . . . ? C23 O3 C20 C21 11.6(2) . . . . ? Li1 O3 C20 C21 -128.78(15) . . . . ? O3 C20 C21 C22A 7.2(4) . . . . ? O3 C20 C21 C22 -26.5(2) . . . . ? C22A C21 C22 C23 -64.0(5) . . . . ? C20 C21 C22 C23 30.7(3) . . . . ? C20 O3 C23 C22A -25.8(4) . . . . ? Li1 O3 C23 C22A 119.4(4) . . . . ? C20 O3 C23 C22 8.0(2) . . . . ? Li1 O3 C23 C22 153.2(2) . . . . ? C21 C22 C23 O3 -24.3(3) . . . . ? C21 C22 C23 C22A 63.8(5) . . . . ? C16 O2 C19A C18 -31.5(8) . . . . ? C19 O2 C19A C18 80.9(13) . . . . ? Li1 O2 C19A C18 162.4(4) . . . . ? C19 C18 C19A O2 -91.2(15) . . . . ? C17 C18 C19A O2 9.2(9) . . . . ? C22 C21 C22A C23 70.5(5) . . . . ? C20 C21 C22A C23 -23.5(6) . . . . ? O3 C23 C22A C21 30.6(6) . . . . ? C22 C23 C22A C21 -70.8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.250 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.042 # Attachment '4a.cif' data_kwh0503m _database_code_depnum_ccdc_archive 'CCDC 287373' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'lithium 2,6-di-t-butyl-4-methoxyphenoxide pyridine' _chemical_melting_point ? _chemical_formula_moiety 'C40 H56 Li2 N2 O4, 2(C5 H5 N)' _chemical_formula_sum 'C50 H66 Li2 N4 O4' _chemical_formula_weight 800.95 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Li Li -0.0003 0.0001 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0509(4) _cell_length_b 10.4419(4) _cell_length_c 12.9636(5) _cell_angle_alpha 79.264(1) _cell_angle_beta 70.309(1) _cell_angle_gamma 63.079(1) _cell_volume 1141.24(8) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9913 _cell_measurement_theta_min 2.374 _cell_measurement_theta_max 28.291 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.165 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9687 _exptl_absorpt_correction_T_max 0.9715 _exptl_absorpt_process_details 'Blessing, R. H. (1995) Acta Cryst. A51, 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Siemens KFFMO2K-90' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12254 _diffrn_reflns_av_R_equivalents 0.0144 _diffrn_reflns_av_sigmaI/netI 0.0194 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 28.29 _reflns_number_total 5639 _reflns_number_gt 5224 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement 'SMART/SAINT (Bruker, 2001)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2001; Sheldrick, 2003)' _computing_structure_solution 'XS (Sheldrick, 2001)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Sheldrick, 1998)' _computing_publication_material 'XCIF (Sheldrick, 2001)' _refine_special_details ; Hydrogen atoms were placed at calculated positions and allowed to ride on the position of the parent atom. Thermal parameters for these hydrogens were set to 1.2\\times the equivalent isotropic U of the parent atom. All non-hydrogen atoms were refined with parameters for anisotropic thermal motion. The largest peak in the final difference map, 0.398e/\%A^3^, was located between C3 and C7. There is one uncoordinated pyridine molecule in the lattice per ASU. No disorder was modelled. 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^)+(0.0630P)^2^+0.2788P] 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 5639 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1109 _refine_ls_wR_factor_gt 0.1086 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 Li1 Li 0.62475(18) 0.90676(18) -0.00452(13) 0.0247(3) Uani 1 1 d . . . O1 O 0.45958(7) 0.98281(6) 0.11469(5) 0.01787(13) Uani 1 1 d . . . O2 O 0.19554(8) 1.00519(7) 0.56561(5) 0.02315(15) Uani 1 1 d . . . N1 N 0.84506(9) 0.76455(8) -0.02067(6) 0.02196(16) Uani 1 1 d . . . N2 N 0.73303(10) 0.45440(9) 0.43088(7) 0.02889(19) Uani 1 1 d . . . C1 C 0.40112(10) 1.08096(9) 0.28698(7) 0.01693(16) Uani 1 1 d . . . C2 C 0.39531(9) 0.98558(9) 0.22346(7) 0.01598(16) Uani 1 1 d . . . C3 C 0.32008(9) 0.89420(9) 0.27904(7) 0.01622(16) Uani 1 1 d . . . C4 C 0.25449(10) 0.89877(9) 0.39335(7) 0.01759(17) Uani 1 1 d . . . H4 H 0.2061 0.8364 0.4302 0.021 Uiso 1 1 calc R . . C5 C 0.25927(10) 0.99272(9) 0.45317(7) 0.01826(17) Uani 1 1 d . . . C6 C 0.33185(10) 1.08254(9) 0.39989(7) 0.01861(17) Uani 1 1 d . . . H6 H 0.3343 1.1468 0.4416 0.022 Uiso 1 1 calc R . . C7 C 0.31141(10) 0.78693(9) 0.21707(7) 0.01760(17) Uani 1 1 d . . . C8 C 0.22980(11) 0.86329(10) 0.12737(7) 0.02229(18) Uani 1 1 d . . . H8A H 0.1254 0.9365 0.1603 0.033 Uiso 1 1 calc R . . H8B H 0.2212 0.7928 0.0925 0.033 Uiso 1 1 calc R . . H8C H 0.2908 0.9092 0.0722 0.033 Uiso 1 1 calc R . . C9 C 0.21984(11) 0.70374(10) 0.29304(7) 0.02326(19) Uani 1 1 d . . . H9A H 0.1129 0.7716 0.3272 0.035 Uiso 1 1 calc R . . H9B H 0.2702 0.6499 0.3502 0.035 Uiso 1 1 calc R . . H9C H 0.2181 0.6368 0.2502 0.035 Uiso 1 1 calc R . . C10 C 0.47665(10) 0.67386(9) 0.16566(7) 0.02120(18) Uani 1 1 d . . . H10A H 0.4711 0.6099 0.1223 0.032 Uiso 1 1 calc R . . H10B H 0.5234 0.6174 0.2239 0.032 Uiso 1 1 calc R . . H10C H 0.5407 0.7222 0.1181 0.032 Uiso 1 1 calc R . . C11 C 0.48792(10) 1.17721(9) 0.23425(7) 0.01892(17) Uani 1 1 d . . . C12 C 0.41952(12) 1.28161(10) 0.14575(8) 0.0258(2) Uani 1 1 d . . . H12A H 0.4394 1.2272 0.0841 0.039 Uiso 1 1 calc R . . H12B H 0.4686 1.3487 0.1200 0.039 Uiso 1 1 calc R . . H12C H 0.3069 1.3355 0.1768 0.039 Uiso 1 1 calc R . . C13 C 0.47677(12) 1.27017(10) 0.31869(8) 0.02412(19) Uani 1 1 d . . . H13A H 0.3671 1.3323 0.3524 0.036 Uiso 1 1 calc R . . H13B H 0.5331 1.3297 0.2819 0.036 Uiso 1 1 calc R . . H13C H 0.5230 1.2078 0.3755 0.036 Uiso 1 1 calc R . . C14 C 0.66227(11) 1.08194(10) 0.18515(8) 0.02330(19) Uani 1 1 d . . . H14A H 0.7061 1.0222 0.2437 0.035 Uiso 1 1 calc R . . H14B H 0.7171 1.1429 0.1493 0.035 Uiso 1 1 calc R . . H14C H 0.6746 1.0201 0.1311 0.035 Uiso 1 1 calc R . . C15 C 0.13788(11) 0.90202(10) 0.62311(7) 0.02110(18) Uani 1 1 d . . . H15A H 0.0467 0.9170 0.6021 0.032 Uiso 1 1 calc R . . H15B H 0.1081 0.9130 0.7022 0.032 Uiso 1 1 calc R . . H15C H 0.2192 0.8050 0.6045 0.032 Uiso 1 1 calc R . . C16 C 0.89277(11) 0.70685(10) 0.06886(8) 0.02346(19) Uani 1 1 d . . . H16 H 0.8171 0.7262 0.1386 0.028 Uiso 1 1 calc R . . C17 C 1.04710(12) 0.62032(11) 0.06466(9) 0.0273(2) Uani 1 1 d . . . H17 H 1.0766 0.5813 0.1300 0.033 Uiso 1 1 calc R . . C18 C 1.15727(11) 0.59207(11) -0.03676(10) 0.0308(2) Uani 1 1 d . . . H18 H 1.2642 0.5339 -0.0422 0.037 Uiso 1 1 calc R . . C19 C 1.10999(12) 0.64958(11) -0.13034(9) 0.0296(2) Uani 1 1 d . . . H19 H 1.1834 0.6308 -0.2010 0.035 Uiso 1 1 calc R . . C20 C 0.95316(11) 0.73518(10) -0.11860(8) 0.02493(19) Uani 1 1 d . . . H20 H 0.9207 0.7749 -0.1828 0.030 Uiso 1 1 calc R . . C21 C 0.63136(11) 0.58890(11) 0.41529(8) 0.02432(19) Uani 1 1 d . . . H21 H 0.5259 0.6064 0.4279 0.029 Uiso 1 1 calc R . . C22 C 0.67125(11) 0.70425(10) 0.38173(8) 0.02423(19) Uani 1 1 d . . . H22 H 0.5953 0.7977 0.3707 0.029 Uiso 1 1 calc R . . C23 C 0.82438(12) 0.67998(11) 0.36465(8) 0.02499(19) Uani 1 1 d . . . H23 H 0.8553 0.7568 0.3426 0.030 Uiso 1 1 calc R . . C24 C 0.93165(11) 0.54131(11) 0.38039(8) 0.0257(2) Uani 1 1 d . . . H24 H 1.0376 0.5211 0.3691 0.031 Uiso 1 1 calc R . . C25 C 0.88079(12) 0.43311(11) 0.41291(9) 0.0283(2) Uani 1 1 d . . . H25 H 0.9549 0.3383 0.4231 0.034 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 0.0211(7) 0.0263(8) 0.0207(7) 0.0003(6) -0.0053(6) -0.0059(6) O1 0.0200(3) 0.0197(3) 0.0139(3) 0.0001(2) -0.0038(2) -0.0094(2) O2 0.0317(4) 0.0247(3) 0.0147(3) -0.0024(2) -0.0008(2) -0.0168(3) N1 0.0196(4) 0.0208(4) 0.0224(4) 0.0006(3) -0.0052(3) -0.0071(3) N2 0.0312(4) 0.0259(4) 0.0323(4) 0.0027(3) -0.0094(3) -0.0156(3) C1 0.0178(4) 0.0157(4) 0.0175(4) 0.0006(3) -0.0056(3) -0.0075(3) C2 0.0156(4) 0.0160(4) 0.0152(4) 0.0001(3) -0.0049(3) -0.0057(3) C3 0.0157(4) 0.0160(4) 0.0169(4) -0.0012(3) -0.0049(3) -0.0063(3) C4 0.0170(4) 0.0181(4) 0.0173(4) -0.0001(3) -0.0034(3) -0.0084(3) C5 0.0187(4) 0.0193(4) 0.0149(4) -0.0013(3) -0.0030(3) -0.0074(3) C6 0.0212(4) 0.0174(4) 0.0180(4) -0.0019(3) -0.0053(3) -0.0086(3) C7 0.0193(4) 0.0181(4) 0.0166(4) -0.0012(3) -0.0041(3) -0.0095(3) C8 0.0251(4) 0.0238(4) 0.0217(4) -0.0011(3) -0.0099(3) -0.0112(3) C9 0.0279(4) 0.0253(4) 0.0214(4) -0.0022(3) -0.0036(3) -0.0172(4) C10 0.0226(4) 0.0181(4) 0.0214(4) -0.0030(3) -0.0043(3) -0.0080(3) C11 0.0227(4) 0.0189(4) 0.0179(4) 0.0010(3) -0.0061(3) -0.0116(3) C12 0.0350(5) 0.0224(4) 0.0250(4) 0.0065(3) -0.0131(4) -0.0160(4) C13 0.0311(5) 0.0234(4) 0.0230(4) -0.0018(3) -0.0062(4) -0.0166(4) C14 0.0228(4) 0.0272(4) 0.0229(4) -0.0019(3) -0.0045(3) -0.0143(4) C15 0.0222(4) 0.0245(4) 0.0168(4) 0.0004(3) -0.0027(3) -0.0125(3) C16 0.0227(4) 0.0234(4) 0.0223(4) -0.0015(3) -0.0057(3) -0.0085(3) C17 0.0268(5) 0.0243(5) 0.0330(5) -0.0016(4) -0.0151(4) -0.0078(4) C18 0.0187(4) 0.0262(5) 0.0445(6) -0.0080(4) -0.0087(4) -0.0048(4) C19 0.0228(4) 0.0275(5) 0.0315(5) -0.0064(4) 0.0022(4) -0.0099(4) C20 0.0262(5) 0.0230(4) 0.0223(4) 0.0011(3) -0.0043(4) -0.0103(4) C21 0.0241(4) 0.0291(5) 0.0218(4) -0.0005(3) -0.0065(3) -0.0132(4) C22 0.0266(5) 0.0226(4) 0.0217(4) -0.0003(3) -0.0072(3) -0.0089(4) C23 0.0307(5) 0.0258(4) 0.0224(4) 0.0002(3) -0.0068(4) -0.0162(4) C24 0.0235(4) 0.0311(5) 0.0242(4) 0.0007(4) -0.0072(4) -0.0134(4) C25 0.0282(5) 0.0235(4) 0.0312(5) 0.0029(4) -0.0102(4) -0.0095(4) _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 O1 1.8192(17) . ? Li1 O1 1.8452(17) 2_675 ? Li1 N1 1.9945(18) . ? Li1 Li1 2.358(3) 2_675 ? O1 C2 1.3382(10) . ? O1 Li1 1.8452(17) 2_675 ? O2 C5 1.3849(10) . ? O2 C15 1.4238(10) . ? N1 C16 1.3391(12) . ? N1 C20 1.3417(12) . ? N2 C21 1.3384(13) . ? N2 C25 1.3404(13) . ? C1 C6 1.3927(11) . ? C1 C2 1.4367(11) . ? C1 C11 1.5409(11) . ? C2 C3 1.4252(11) . ? C3 C4 1.4045(11) . ? C3 C7 1.5422(11) . ? C4 C5 1.3847(12) . ? C4 H4 0.9500 . ? C5 C6 1.3883(12) . ? C6 H6 0.9500 . ? C7 C9 1.5382(12) . ? C7 C8 1.5382(12) . ? C7 C10 1.5388(12) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.5375(12) . ? C11 C13 1.5389(12) . ? C11 C14 1.5399(13) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.3848(13) . ? C16 H16 0.9500 . ? C17 C18 1.3818(15) . ? C17 H17 0.9500 . ? C18 C19 1.3845(16) . ? C18 H18 0.9500 . ? C19 C20 1.3856(14) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C22 1.3875(13) . ? C21 H21 0.9500 . ? C22 C23 1.3857(14) . ? C22 H22 0.9500 . ? C23 C24 1.3875(14) . ? C23 H23 0.9500 . ? C24 C25 1.3841(14) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? 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 O1 Li1 O1 99.91(8) . 2_675 ? O1 Li1 N1 132.58(9) . . ? O1 Li1 N1 127.10(9) 2_675 . ? O1 Li1 Li1 50.44(6) . 2_675 ? O1 Li1 Li1 49.47(6) 2_675 2_675 ? N1 Li1 Li1 173.76(13) . 2_675 ? C2 O1 Li1 150.19(7) . . ? C2 O1 Li1 129.72(7) . 2_675 ? Li1 O1 Li1 80.09(8) . 2_675 ? C5 O2 C15 116.37(7) . . ? C16 N1 C20 117.69(8) . . ? C16 N1 Li1 119.66(8) . . ? C20 N1 Li1 122.26(8) . . ? C21 N2 C25 116.81(9) . . ? C6 C1 C2 119.24(7) . . ? C6 C1 C11 118.96(7) . . ? C2 C1 C11 121.75(7) . . ? O1 C2 C3 121.03(7) . . ? O1 C2 C1 120.52(7) . . ? C3 C2 C1 118.45(7) . . ? C4 C3 C2 119.80(7) . . ? C4 C3 C7 118.55(7) . . ? C2 C3 C7 121.64(7) . . ? C5 C4 C3 121.01(8) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 O2 124.53(8) . . ? C4 C5 C6 119.71(8) . . ? O2 C5 C6 115.76(7) . . ? C5 C6 C1 121.78(8) . . ? C5 C6 H6 119.1 . . ? C1 C6 H6 119.1 . . ? C9 C7 C8 106.44(7) . . ? C9 C7 C10 106.48(7) . . ? C8 C7 C10 109.76(7) . . ? C9 C7 C3 112.50(7) . . ? C8 C7 C3 111.68(7) . . ? C10 C7 C3 109.79(7) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C13 106.54(7) . . ? C12 C11 C14 110.55(7) . . ? C13 C11 C14 106.82(7) . . ? C12 C11 C1 111.42(7) . . ? C13 C11 C1 112.06(7) . . ? C14 C11 C1 109.33(7) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O2 C15 H15A 109.5 . . ? O2 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O2 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N1 C16 C17 123.16(9) . . ? N1 C16 H16 118.4 . . ? C17 C16 H16 118.4 . . ? C18 C17 C16 118.48(9) . . ? C18 C17 H17 120.8 . . ? C16 C17 H17 120.8 . . ? C17 C18 C19 119.21(9) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? C18 C19 C20 118.49(9) . . ? C18 C19 H19 120.8 . . ? C20 C19 H19 120.8 . . ? N1 C20 C19 122.96(9) . . ? N1 C20 H20 118.5 . . ? C19 C20 H20 118.5 . . ? N2 C21 C22 123.71(9) . . ? N2 C21 H21 118.1 . . ? C22 C21 H21 118.1 . . ? C23 C22 C21 118.48(9) . . ? C23 C22 H22 120.8 . . ? C21 C22 H22 120.8 . . ? C22 C23 C24 118.72(9) . . ? C22 C23 H23 120.6 . . ? C24 C23 H23 120.6 . . ? C25 C24 C23 118.48(9) . . ? C25 C24 H24 120.8 . . ? C23 C24 H24 120.8 . . ? N2 C25 C24 123.79(9) . . ? N2 C25 H25 118.1 . . ? C24 C25 H25 118.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Li1 O1 C2 179.41(13) 2_675 . . . ? N1 Li1 O1 C2 -7.8(3) . . . . ? Li1 Li1 O1 C2 179.41(13) 2_675 . . . ? O1 Li1 O1 Li1 0.0 2_675 . . 2_675 ? N1 Li1 O1 Li1 172.75(19) . . . 2_675 ? O1 Li1 N1 C16 0.17(17) . . . . ? O1 Li1 N1 C16 171.20(10) 2_675 . . . ? O1 Li1 N1 C20 -172.48(11) . . . . ? O1 Li1 N1 C20 -1.46(17) 2_675 . . . ? Li1 O1 C2 C3 -86.47(17) . . . . ? Li1 O1 C2 C3 92.78(11) 2_675 . . . ? Li1 O1 C2 C1 93.37(17) . . . . ? Li1 O1 C2 C1 -87.39(11) 2_675 . . . ? C6 C1 C2 O1 179.35(7) . . . . ? C11 C1 C2 O1 -3.24(12) . . . . ? C6 C1 C2 C3 -0.81(12) . . . . ? C11 C1 C2 C3 176.60(7) . . . . ? O1 C2 C3 C4 179.60(7) . . . . ? C1 C2 C3 C4 -0.23(12) . . . . ? O1 C2 C3 C7 0.92(12) . . . . ? C1 C2 C3 C7 -178.91(7) . . . . ? C2 C3 C4 C5 1.12(13) . . . . ? C7 C3 C4 C5 179.84(7) . . . . ? C3 C4 C5 O2 179.06(8) . . . . ? C3 C4 C5 C6 -0.93(13) . . . . ? C15 O2 C5 C4 7.49(12) . . . . ? C15 O2 C5 C6 -172.52(7) . . . . ? C4 C5 C6 C1 -0.16(13) . . . . ? O2 C5 C6 C1 179.85(8) . . . . ? C2 C1 C6 C5 1.03(13) . . . . ? C11 C1 C6 C5 -176.46(8) . . . . ? C4 C3 C7 C9 3.36(11) . . . . ? C2 C3 C7 C9 -177.94(8) . . . . ? C4 C3 C7 C8 122.99(8) . . . . ? C2 C3 C7 C8 -58.31(10) . . . . ? C4 C3 C7 C10 -115.02(8) . . . . ? C2 C3 C7 C10 63.68(10) . . . . ? C6 C1 C11 C12 -122.18(9) . . . . ? C2 C1 C11 C12 60.40(10) . . . . ? C6 C1 C11 C13 -2.91(11) . . . . ? C2 C1 C11 C13 179.67(8) . . . . ? C6 C1 C11 C14 115.33(9) . . . . ? C2 C1 C11 C14 -62.09(10) . . . . ? C20 N1 C16 C17 0.55(14) . . . . ? Li1 N1 C16 C17 -172.43(9) . . . . ? N1 C16 C17 C18 0.00(15) . . . . ? C16 C17 C18 C19 -0.64(15) . . . . ? C17 C18 C19 C20 0.72(15) . . . . ? C16 N1 C20 C19 -0.47(14) . . . . ? Li1 N1 C20 C19 172.32(10) . . . . ? C18 C19 C20 N1 -0.16(15) . . . . ? C25 N2 C21 C22 0.29(15) . . . . ? N2 C21 C22 C23 -0.91(15) . . . . ? C21 C22 C23 C24 0.83(14) . . . . ? C22 C23 C24 C25 -0.22(14) . . . . ? C21 N2 C25 C24 0.39(16) . . . . ? C23 C24 C25 N2 -0.42(16) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.398 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.046 _exptl_crystal_recrystallization_method 'slow cooling of a pyridine solution from 60 to 20 degrees centigrade '