# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 182/1291 data_rs96 #(Compound 1) _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H40 Li2 N2 O2 P2' _chemical_formula_weight 560.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Li' 'Li' -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.6829(17) _cell_length_b 10.2903(14) _cell_length_c 24.527(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.782(3) _cell_angle_gamma 90.00 _cell_volume 3163.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 7308 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 27.96 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.177 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.167 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6166 _exptl_absorpt_correction_T_max 1.0000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(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 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 16008 _diffrn_reflns_av_R_equivalents 0.0733 _diffrn_reflns_av_sigmaI/netI 0.0917 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5560 _reflns_number_gt 3437 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'SHELXTL and local programs' _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 w=1/[\s^2^(Fo^2^)+(0.1110P)^2^+15.4235P] 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 5560 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1500 _refine_ls_R_factor_gt 0.1039 _refine_ls_wR_factor_ref 0.3095 _refine_ls_wR_factor_gt 0.2926 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Li1 Li 0.9051(9) 1.1736(12) 0.1096(5) 0.043(3) Uani 1 d . . . Li2 Li 0.9517(9) 0.9446(11) 0.0374(4) 0.038(3) Uani 1 d . . . P1 P 0.85663(13) 0.86090(19) 0.11623(7) 0.0362(5) Uani 1 d . . . O1 O 0.8646(3) 1.0008(5) 0.09604(18) 0.0389(11) Uani 1 d . . . C1 C 0.9279(5) 0.8478(8) 0.1864(3) 0.0428(19) Uani 1 d . . . C2 C 0.9797(6) 0.9546(10) 0.2125(3) 0.061(2) Uani 1 d . . . H2 H 0.9776 1.0357 0.1939 0.073 Uiso 1 calc R . . C3 C 1.0346(7) 0.9434(13) 0.2656(4) 0.078(3) Uani 1 d . . . H3 H 1.0712 1.0164 0.2831 0.093 Uiso 1 calc R . . C4 C 1.0362(8) 0.8272(16) 0.2930(4) 0.093(4) Uani 1 d . . . H4 H 1.0707 0.8206 0.3301 0.111 Uiso 1 calc R . . C5 C 0.9884(8) 0.7219(13) 0.2670(4) 0.081(3) Uani 1 d . . . H5 H 0.9921 0.6409 0.2857 0.098 Uiso 1 calc R . . C6 C 0.9344(6) 0.7297(10) 0.2137(3) 0.065(3) Uani 1 d . . . H6 H 0.9020 0.6546 0.1959 0.078 Uiso 1 calc R . . C7 C 0.7153(5) 0.8388(7) 0.1222(3) 0.0397(17) Uani 1 d . . . C8 C 0.6754(6) 0.7154(9) 0.1285(3) 0.054(2) Uani 1 d . . . H8 H 0.7225 0.6432 0.1307 0.065 Uiso 1 calc R . . C9 C 0.5683(7) 0.6942(10) 0.1316(3) 0.063(2) Uani 1 d . . . H9 H 0.5426 0.6085 0.1352 0.076 Uiso 1 calc R . . C10 C 0.5005(6) 0.7975(11) 0.1295(3) 0.064(3) Uani 1 d . . . H10 H 0.4274 0.7840 0.1323 0.077 Uiso 1 calc R . . C11 C 0.5385(6) 0.9235(11) 0.1230(3) 0.064(3) Uani 1 d . . . H11 H 0.4913 0.9957 0.1207 0.077 Uiso 1 calc R . . C12 C 0.6454(6) 0.9416(8) 0.1199(3) 0.0492(19) Uani 1 d . . . H12 H 0.6713 1.0273 0.1162 0.059 Uiso 1 calc R . . C13 C 0.9064(6) 0.7491(7) 0.0767(3) 0.0397(17) Uani 1 d . . . H13A H 0.8529 0.6952 0.0533 0.048 Uiso 1 calc R . . H13B H 0.9671 0.6973 0.0955 0.048 Uiso 1 calc R . . P2 P 1.14615(13) 1.11802(19) 0.08906(7) 0.0372(5) Uani 1 d . . . O2 O 1.0853(3) 1.0427(5) 0.04074(17) 0.0384(11) Uani 1 d . . . C14 C 1.2611(5) 1.1925(8) 0.0641(3) 0.0408(17) Uani 1 d . . . C15 C 1.2819(6) 1.3272(8) 0.0724(4) 0.057(2) Uani 1 d . . . H15 H 1.2359 1.3790 0.0906 0.068 Uiso 1 calc R . . C16 C 1.3686(7) 1.3826(9) 0.0541(4) 0.065(2) Uani 1 d . . . H16 H 1.3825 1.4724 0.0608 0.078 Uiso 1 calc R . . C17 C 1.4348(6) 1.3132(9) 0.0268(3) 0.055(2) Uani 1 d . . . H17 H 1.4935 1.3540 0.0139 0.067 Uiso 1 calc R . . C18 C 1.4159(7) 1.1845(10) 0.0182(4) 0.066(2) Uani 1 d . . . H18 H 1.4625 1.1340 -0.0002 0.079 Uiso 1 calc R . . C19 C 1.3288(6) 1.1269(9) 0.0360(4) 0.059(2) Uani 1 d . . . H19 H 1.3158 1.0374 0.0284 0.070 Uiso 1 calc R . . C20 C 1.2057(5) 1.0007(8) 0.1398(3) 0.0390(17) Uani 1 d . . . C21 C 1.2740(5) 1.0406(9) 0.1876(3) 0.052(2) Uani 1 d . . . H21 H 1.2913 1.1299 0.1930 0.062 Uiso 1 calc R . . C22 C 1.3158(6) 0.9509(12) 0.2267(3) 0.069(3) Uani 1 d . . . H22 H 1.3628 0.9783 0.2586 0.083 Uiso 1 calc R . . C23 C 1.2886(7) 0.8185(12) 0.2195(3) 0.068(3) Uani 1 d . . . H23 H 1.3169 0.7565 0.2465 0.081 Uiso 1 calc R . . C24 C 1.2223(6) 0.7804(10) 0.1740(4) 0.063(2) Uani 1 d . . . H24 H 1.2032 0.6913 0.1696 0.075 Uiso 1 calc R . . C25 C 1.1813(5) 0.8688(8) 0.1333(3) 0.0475(19) Uani 1 d . . . H25 H 1.1365 0.8393 0.1010 0.057 Uiso 1 calc R . . C26 C 1.0732(5) 1.2241(8) 0.1218(3) 0.0466(19) Uani 1 d . . . H26A H 1.0816 1.3129 0.1076 0.056 Uiso 1 calc R . . H26B H 1.1010 1.2241 0.1618 0.056 Uiso 1 calc R . . N1 N 0.8263(5) 1.2777(7) 0.1698(2) 0.0496(17) Uani 1 d . . . N2 N 0.8196(5) 1.3033(6) 0.0488(2) 0.0454(15) Uani 1 d . . . C27 C 0.8993(7) 1.3757(10) 0.1957(4) 0.077(3) Uani 1 d . . . H27A H 0.8618 1.4328 0.2183 0.115 Uiso 1 calc R . . H27B H 0.9264 1.4271 0.1672 0.115 Uiso 1 calc R . . H27C H 0.9590 1.3333 0.2191 0.115 Uiso 1 calc R . . C28 C 0.7841(7) 1.2060(10) 0.2129(3) 0.067(2) Uani 1 d . . . H28A H 0.8430 1.1647 0.2373 0.100 Uiso 1 calc R . . H28B H 0.7345 1.1391 0.1961 0.100 Uiso 1 calc R . . H28C H 0.7465 1.2659 0.2343 0.100 Uiso 1 calc R . . C29 C 0.7361(6) 1.3386(9) 0.1325(3) 0.057(2) Uani 1 d . . . H29A H 0.6803 1.2722 0.1217 0.068 Uiso 1 calc R . . H29B H 0.7047 1.4080 0.1528 0.068 Uiso 1 calc R . . C30 C 0.7683(6) 1.3947(8) 0.0820(3) 0.055(2) Uani 1 d . . . H30A H 0.7041 1.4308 0.0589 0.066 Uiso 1 calc R . . H30B H 0.8179 1.4678 0.0928 0.066 Uiso 1 calc R . . C31 C 0.8863(7) 1.3724(8) 0.0135(3) 0.058(2) Uani 1 d . . . H31A H 0.9254 1.3089 -0.0055 0.087 Uiso 1 calc R . . H31B H 0.9371 1.4290 0.0365 0.087 Uiso 1 calc R . . H31C H 0.8405 1.4250 -0.0138 0.087 Uiso 1 calc R . . C32 C 0.7410(6) 1.2243(8) 0.0143(3) 0.053(2) Uani 1 d . . . H32A H 0.6977 1.1771 0.0376 0.080 Uiso 1 calc R . . H32B H 0.7776 1.1621 -0.0066 0.080 Uiso 1 calc R . . H32C H 0.6949 1.2805 -0.0114 0.080 Uiso 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 0.035(6) 0.048(8) 0.047(6) -0.006(6) 0.009(5) 0.003(5) Li2 0.040(6) 0.039(7) 0.037(6) 0.004(5) 0.010(5) 0.000(5) P1 0.0327(9) 0.0449(12) 0.0322(9) 0.0056(8) 0.0087(7) -0.0009(8) O1 0.040(3) 0.038(3) 0.040(2) 0.003(2) 0.010(2) -0.001(2) C1 0.028(3) 0.070(6) 0.032(3) 0.004(4) 0.011(3) 0.004(4) C2 0.048(5) 0.087(7) 0.046(4) -0.006(5) 0.003(4) 0.014(5) C3 0.062(6) 0.120(10) 0.048(5) -0.012(6) 0.001(4) 0.020(6) C4 0.050(6) 0.186(14) 0.041(5) 0.013(7) 0.005(4) 0.039(7) C5 0.057(6) 0.133(10) 0.056(6) 0.039(6) 0.015(5) 0.018(6) C6 0.040(4) 0.095(8) 0.058(5) 0.031(5) 0.003(4) 0.009(4) C7 0.038(4) 0.049(5) 0.033(3) 0.005(3) 0.010(3) 0.000(3) C8 0.045(4) 0.064(6) 0.055(5) 0.018(4) 0.013(4) -0.006(4) C9 0.062(5) 0.071(7) 0.058(5) 0.010(5) 0.017(4) -0.019(5) C10 0.032(4) 0.108(8) 0.054(5) 0.000(5) 0.012(3) -0.004(5) C11 0.038(4) 0.095(8) 0.061(5) -0.004(5) 0.011(4) 0.013(5) C12 0.042(4) 0.059(5) 0.047(4) -0.001(4) 0.007(3) 0.002(4) C13 0.045(4) 0.035(4) 0.040(4) 0.004(3) 0.009(3) 0.002(3) P2 0.0288(9) 0.0478(12) 0.0337(9) -0.0016(8) 0.0003(7) -0.0033(8) O2 0.033(2) 0.048(3) 0.033(2) 0.004(2) 0.0015(19) -0.006(2) C14 0.030(3) 0.049(5) 0.039(4) -0.001(3) -0.007(3) -0.009(3) C15 0.041(4) 0.050(6) 0.076(6) 0.000(4) -0.002(4) -0.001(4) C16 0.062(5) 0.038(5) 0.089(6) 0.008(5) -0.010(5) -0.012(4) C17 0.046(5) 0.066(6) 0.054(5) 0.014(4) 0.007(4) -0.009(4) C18 0.059(5) 0.067(7) 0.076(6) -0.009(5) 0.026(4) -0.014(5) C19 0.054(5) 0.046(5) 0.079(6) -0.010(4) 0.024(4) -0.014(4) C20 0.026(3) 0.061(5) 0.031(3) 0.002(3) 0.007(3) -0.001(3) C21 0.034(4) 0.078(6) 0.041(4) 0.004(4) 0.002(3) 0.003(4) C22 0.043(5) 0.126(10) 0.036(4) 0.003(5) -0.003(3) 0.010(5) C23 0.052(5) 0.103(8) 0.048(5) 0.033(5) 0.010(4) 0.017(5) C24 0.038(4) 0.077(7) 0.073(6) 0.026(5) 0.007(4) 0.006(4) C25 0.034(4) 0.066(6) 0.043(4) 0.012(4) 0.007(3) 0.004(4) C26 0.033(4) 0.062(5) 0.045(4) -0.007(4) 0.007(3) 0.001(3) N1 0.045(4) 0.071(5) 0.035(3) -0.013(3) 0.015(3) 0.000(3) N2 0.043(3) 0.052(4) 0.041(3) -0.003(3) 0.007(3) -0.002(3) C27 0.069(6) 0.089(8) 0.074(6) -0.032(6) 0.019(5) -0.009(6) C28 0.066(6) 0.087(7) 0.051(5) -0.005(5) 0.019(4) 0.009(5) C29 0.051(5) 0.057(6) 0.066(5) -0.004(4) 0.021(4) 0.002(4) C30 0.052(5) 0.051(5) 0.065(5) -0.008(4) 0.018(4) 0.001(4) C31 0.070(5) 0.050(5) 0.059(5) 0.004(4) 0.024(4) -0.007(4) C32 0.046(4) 0.060(6) 0.052(4) -0.001(4) -0.002(3) -0.001(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 1.866(13) . ? Li1 N2 2.165(14) . ? Li1 C26 2.171(13) . ? Li1 N1 2.185(12) . ? Li1 Li2 3.058(16) . ? Li2 O2 1.907(11) 3_775 ? Li2 O2 1.963(12) . ? Li2 O1 2.026(12) . ? Li2 C13 2.340(13) . ? Li2 P1 2.577(11) . ? Li2 Li2 2.62(2) 3_775 ? P1 O1 1.531(5) . ? P1 C13 1.687(7) . ? P1 C1 1.823(7) . ? P1 C7 1.834(7) . ? C1 C6 1.383(11) . ? C1 C2 1.386(12) . ? C2 C3 1.385(11) . ? C3 C4 1.370(16) . ? C4 C5 1.352(16) . ? C5 C6 1.382(12) . ? C7 C12 1.377(10) . ? C7 C8 1.384(11) . ? C8 C9 1.389(11) . ? C9 C10 1.363(13) . ? C10 C11 1.401(13) . ? C11 C12 1.381(11) . ? P2 O2 1.524(5) . ? P2 C26 1.708(7) . ? P2 C20 1.813(7) . ? P2 C14 1.833(7) . ? O2 Li2 1.907(11) 3_775 ? C14 C19 1.359(11) . ? C14 C15 1.420(11) . ? C15 C16 1.372(12) . ? C16 C17 1.355(12) . ? C17 C18 1.356(13) . ? C18 C19 1.383(11) . ? C20 C25 1.396(11) . ? C20 C21 1.410(9) . ? C21 C22 1.377(12) . ? C22 C23 1.410(14) . ? C23 C24 1.349(13) . ? C24 C25 1.392(11) . ? N1 C27 1.448(11) . ? N1 C28 1.457(10) . ? N1 C29 1.489(10) . ? N2 C32 1.453(9) . ? N2 C30 1.461(9) . ? N2 C31 1.482(9) . ? C29 C30 1.478(11) . ? 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 N2 111.7(6) . . ? O1 Li1 C26 119.4(6) . . ? N2 Li1 C26 109.0(6) . . ? O1 Li1 N1 116.5(6) . . ? N2 Li1 N1 86.0(5) . . ? C26 Li1 N1 109.3(6) . . ? O1 Li1 Li2 40.1(3) . . ? N2 Li1 Li2 101.4(5) . . ? C26 Li1 Li2 89.5(5) . . ? N1 Li1 Li2 156.6(6) . . ? O2 Li2 O2 94.8(5) 3_775 . ? O2 Li2 O1 128.1(6) 3_775 . ? O2 Li2 O1 112.6(6) . . ? O2 Li2 C13 115.8(6) 3_775 . ? O2 Li2 C13 133.6(6) . . ? O1 Li2 C13 76.0(4) . . ? O2 Li2 P1 134.9(6) 3_775 . ? O2 Li2 P1 129.8(5) . . ? O1 Li2 P1 36.4(2) . . ? C13 Li2 P1 39.8(2) . . ? O2 Li2 Li2 48.3(4) 3_775 3_775 ? O2 Li2 Li2 46.5(4) . 3_775 ? O1 Li2 Li2 137.5(8) . 3_775 ? C13 Li2 Li2 146.4(8) . 3_775 ? P1 Li2 Li2 173.6(8) . 3_775 ? O2 Li2 Li1 119.3(6) 3_775 . ? O2 Li2 Li1 79.8(4) . . ? O1 Li2 Li1 36.4(3) . . ? C13 Li2 Li1 110.0(5) . . ? P1 Li2 Li1 70.7(3) . . ? Li2 Li2 Li1 102.9(6) 3_775 . ? O1 P1 C13 114.0(3) . . ? O1 P1 C1 109.1(3) . . ? C13 P1 C1 108.5(3) . . ? O1 P1 C7 104.8(3) . . ? C13 P1 C7 114.6(3) . . ? C1 P1 C7 105.4(3) . . ? O1 P1 Li2 51.8(3) . . ? C13 P1 Li2 62.5(4) . . ? C1 P1 Li2 120.8(3) . . ? C7 P1 Li2 132.5(3) . . ? P1 O1 Li1 150.2(5) . . ? P1 O1 Li2 91.8(4) . . ? Li1 O1 Li2 103.5(5) . . ? C6 C1 C2 119.0(7) . . ? C6 C1 P1 120.4(6) . . ? C2 C1 P1 120.6(6) . . ? C3 C2 C1 120.2(9) . . ? C4 C3 C2 120.1(11) . . ? C5 C4 C3 119.7(9) . . ? C4 C5 C6 121.4(11) . . ? C5 C6 C1 119.5(10) . . ? C12 C7 C8 117.7(7) . . ? C12 C7 P1 122.2(6) . . ? C8 C7 P1 120.1(6) . . ? C7 C8 C9 121.9(8) . . ? C10 C9 C8 119.5(9) . . ? C9 C10 C11 120.0(7) . . ? C12 C11 C10 119.3(8) . . ? C7 C12 C11 121.7(8) . . ? P1 C13 Li2 77.7(4) . . ? O2 P2 C26 116.4(3) . . ? O2 P2 C20 107.6(3) . . ? C26 P2 C20 107.6(3) . . ? O2 P2 C14 106.7(3) . . ? C26 P2 C14 113.9(4) . . ? C20 P2 C14 103.8(3) . . ? P2 O2 Li2 139.8(5) . 3_775 ? P2 O2 Li2 128.7(4) . . ? Li2 O2 Li2 85.2(5) 3_775 . ? C19 C14 C15 116.0(7) . . ? C19 C14 P2 123.9(6) . . ? C15 C14 P2 120.0(6) . . ? C16 C15 C14 119.9(8) . . ? C17 C16 C15 122.0(8) . . ? C16 C17 C18 119.0(8) . . ? C17 C18 C19 120.0(8) . . ? C14 C19 C18 123.0(8) . . ? C25 C20 C21 118.4(7) . . ? C25 C20 P2 120.5(5) . . ? C21 C20 P2 121.1(6) . . ? C22 C21 C20 120.5(9) . . ? C21 C22 C23 119.9(8) . . ? C24 C23 C22 119.7(8) . . ? C23 C24 C25 121.3(9) . . ? C24 C25 C20 120.1(7) . . ? P2 C26 Li1 111.9(5) . . ? C27 N1 C28 108.3(7) . . ? C27 N1 C29 110.9(7) . . ? C28 N1 C29 109.0(6) . . ? C27 N1 Li1 108.1(6) . . ? C28 N1 Li1 119.9(6) . . ? C29 N1 Li1 100.3(5) . . ? C32 N2 C30 111.2(6) . . ? C32 N2 C31 109.2(6) . . ? C30 N2 C31 111.0(6) . . ? C32 N2 Li1 106.5(6) . . ? C30 N2 Li1 103.4(5) . . ? C31 N2 Li1 115.3(6) . . ? C30 C29 N1 113.2(6) . . ? N2 C30 C29 114.7(7) . . ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.940 _refine_diff_density_max 0.687 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.090 data_rs9820 #(Compound 2) _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18.88 H22.25 Li N O P' _chemical_formula_weight 317.04 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Li' 'Li' -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y+1/2, x, z' 'y, -x+1/2, z' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y-1/2, -x, -z' '-y, x-1/2, -z' _cell_length_a 16.472(2) _cell_length_b 16.472(2) _cell_length_c 13.664(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3707.4(10) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.136 _exptl_crystal_density_method ? _exptl_crystal_F_000 1348 _exptl_absorpt_coefficient_mu 0.150 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6540 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0501 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.80 _diffrn_reflns_theta_max 24.98 _reflns_number_total 3270 _reflns_number_observed 2390 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 2 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0939P)^2^+3.7737P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3268 _refine_ls_number_parameters 206 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0858 _refine_ls_R_factor_obs 0.0618 _refine_ls_wR_factor_all 0.2018 _refine_ls_wR_factor_obs 0.1774 _refine_ls_goodness_of_fit_all 1.068 _refine_ls_goodness_of_fit_obs 1.112 _refine_ls_restrained_S_all 1.073 _refine_ls_restrained_S_obs 1.112 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P1 P 0.66303(5) 0.13325(5) 0.16090(6) 0.0356(3) Uani 1 d . . O1 O 0.68513(13) 0.18794(12) 0.07458(15) 0.0364(5) Uani 1 d . . N1 N 0.8406(2) 0.1116(2) 0.1684(2) 0.0472(7) Uani 1 d . . H1A H 0.8782(2) 0.0751(2) 0.1556(2) 0.057 Uiso 1 calc R . C1 C 0.8085(3) 0.1040(4) 0.4406(3) 0.087(2) Uani 1 d . . H1C H 0.7861(3) 0.1591(4) 0.4449(3) 0.130 Uiso 1 calc R . H1D H 0.8443(3) 0.0941(4) 0.4966(3) 0.130 Uiso 1 calc R . H1E H 0.7640(3) 0.0645(4) 0.4412(3) 0.130 Uiso 1 calc R . Li1 Li 0.6897(3) 0.1925(3) -0.0680(4) 0.0402(12) Uani 1 d . . C2 C 0.8913(3) 0.0111(3) 0.3385(3) 0.0823(15) Uani 1 d . . H2A H 0.9219(3) 0.0069(3) 0.2772(3) 0.123 Uiso 1 calc R . H2B H 0.8473(3) -0.0290(3) 0.3385(3) 0.123 Uiso 1 calc R . H2C H 0.9276(3) 0.0006(3) 0.3939(3) 0.123 Uiso 1 calc R . C3 C 0.9280(3) 0.1548(3) 0.3553(4) 0.0777(14) Uani 1 d . . H3A H 0.9610(3) 0.1513(3) 0.2957(4) 0.117 Uiso 1 calc R . H3B H 0.9614(3) 0.1404(3) 0.4121(4) 0.117 Uiso 1 calc R . H3C H 0.9076(3) 0.2103(3) 0.3629(4) 0.117 Uiso 1 calc R . C4 C 0.8558(2) 0.0955(2) 0.3476(3) 0.0487(9) Uani 1 d . . C5 C 0.8062(2) 0.1143(2) 0.2547(2) 0.0408(8) Uani 1 d . . C6 C 0.7238(2) 0.1340(2) 0.2618(2) 0.0403(8) Uani 1 d . . H6A H 0.7014(2) 0.1480(2) 0.3237(2) 0.048 Uiso 1 calc R . C7 C 0.5618(2) 0.1579(2) 0.2014(3) 0.0410(8) Uani 1 d . . C8 C 0.5292(2) 0.1202(2) 0.2835(3) 0.0526(9) Uani 1 d . . H8A H 0.5602(2) 0.0810(2) 0.3181(3) 0.063 Uiso 1 calc R . C9 C 0.4520(3) 0.1395(3) 0.3149(3) 0.0635(11) Uani 1 d . . H9A H 0.4300(3) 0.1140(3) 0.3713(3) 0.076 Uiso 1 calc R . C10 C 0.4066(2) 0.1962(3) 0.2641(3) 0.0624(11) Uani 1 d . . H10A H 0.3537(2) 0.2099(3) 0.2860(3) 0.075 Uiso 1 calc R . C11 C 0.4377(2) 0.2325(2) 0.1826(3) 0.0561(10) Uani 1 d . . H11A H 0.4061(2) 0.2710(2) 0.1475(3) 0.067 Uiso 1 calc R . C12 C 0.5150(2) 0.2135(2) 0.1509(3) 0.0476(8) Uani 1 d . . H12A H 0.5361(2) 0.2389(2) 0.0939(3) 0.057 Uiso 1 calc R . C13 C 0.6516(2) 0.0310(2) 0.1138(2) 0.0397(8) Uani 1 d . . C14 C 0.6740(2) -0.0361(2) 0.1696(3) 0.0491(9) Uani 1 d . . H14A H 0.7010(2) -0.0286(2) 0.2303(3) 0.059 Uiso 1 calc R . C15 C 0.6571(2) -0.1136(2) 0.1369(3) 0.0594(10) Uani 1 d . . H15A H 0.6726(2) -0.1591(2) 0.1753(3) 0.071 Uiso 1 calc R . C16 C 0.6178(2) -0.1255(2) 0.0490(3) 0.0582(10) Uani 1 d . . H16A H 0.6058(2) -0.1789(2) 0.0274(3) 0.070 Uiso 1 calc R . C17 C 0.5963(3) -0.0600(2) -0.0070(3) 0.0591(10) Uani 1 d . . H17A H 0.5701(3) -0.0680(2) -0.0682(3) 0.071 Uiso 1 calc R . C18 C 0.6126(2) 0.0179(2) 0.0255(3) 0.0501(9) Uani 1 d . . H18A H 0.5969(2) 0.0630(2) -0.0133(3) 0.060 Uiso 1 calc R . C50 C 0.1888(11) 0.2236(17) 0.5345(19) 0.069(4) Uiso 0.13 d PG . C51 C 0.2601(18) 0.1787(10) 0.5292(24) 0.069(4) Uiso 0.13 d PG . C52 C 0.3348(12) 0.2180(16) 0.5286(30) 0.069(4) Uiso 0.13 d PG . C53 C 0.3382(12) 0.3022(17) 0.5333(21) 0.069(4) Uiso 0.13 d PG . C54 C 0.2669(18) 0.3471(10) 0.5386(25) 0.069(4) Uiso 0.13 d PG . C55 C 0.1922(13) 0.3078(16) 0.5393(29) 0.069(4) Uiso 0.13 d PG . 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 P1 0.0359(5) 0.0317(5) 0.0390(5) 0.0008(3) 0.0030(3) -0.0019(3) O1 0.0359(11) 0.0337(11) 0.0396(12) 0.0015(9) 0.0015(9) -0.0019(9) N1 0.044(2) 0.052(2) 0.045(2) 0.0052(13) 0.0052(13) 0.0130(13) C1 0.072(3) 0.135(5) 0.053(2) 0.012(3) -0.004(2) 0.011(3) Li1 0.040(3) 0.038(3) 0.042(3) 0.001(2) -0.001(2) 0.000(2) C2 0.099(4) 0.076(3) 0.072(3) 0.013(2) -0.019(3) 0.025(3) C3 0.071(3) 0.092(4) 0.070(3) 0.010(3) -0.017(2) -0.011(3) C4 0.053(2) 0.050(2) 0.043(2) 0.007(2) -0.003(2) 0.002(2) C5 0.046(2) 0.033(2) 0.043(2) 0.0027(14) 0.0001(15) -0.0006(14) C6 0.047(2) 0.038(2) 0.036(2) 0.0003(14) 0.0030(14) -0.0016(14) C7 0.040(2) 0.035(2) 0.048(2) -0.0048(15) 0.0045(15) -0.0040(14) C8 0.050(2) 0.043(2) 0.065(2) 0.006(2) 0.014(2) -0.003(2) C9 0.059(2) 0.054(2) 0.078(3) 0.002(2) 0.027(2) -0.010(2) C10 0.043(2) 0.055(2) 0.089(3) -0.011(2) 0.019(2) -0.005(2) C11 0.043(2) 0.048(2) 0.077(3) -0.007(2) 0.002(2) 0.003(2) C12 0.043(2) 0.042(2) 0.057(2) 0.001(2) 0.003(2) -0.001(2) C13 0.039(2) 0.035(2) 0.045(2) -0.0007(14) 0.0078(15) -0.0035(13) C14 0.050(2) 0.037(2) 0.060(2) 0.001(2) -0.002(2) -0.002(2) C15 0.058(2) 0.036(2) 0.084(3) 0.005(2) -0.002(2) -0.001(2) C16 0.056(2) 0.039(2) 0.080(3) -0.009(2) 0.004(2) -0.006(2) C17 0.069(3) 0.050(2) 0.059(2) -0.011(2) -0.002(2) -0.015(2) C18 0.058(2) 0.041(2) 0.052(2) 0.002(2) -0.001(2) -0.008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.528(2) . ? P1 C6 1.704(3) . ? P1 C7 1.803(3) . ? P1 C13 1.813(3) . ? P1 Li1 2.854(5) 8_655 ? O1 Li1 1.951(6) . ? O1 Li1 2.019(6) 8_655 ? O1 Li1 2.020(6) 7_665 ? N1 C5 1.310(4) . ? N1 Li1 1.958(6) 8_655 ? C1 C4 1.498(6) . ? Li1 N1 1.958(6) 7_665 ? Li1 O1 2.019(6) 7_665 ? Li1 O1 2.020(6) 8_655 ? Li1 Li1 2.687(9) 8_655 ? Li1 Li1 2.687(9) 7_665 ? Li1 Li1 2.745(11) 2_655 ? Li1 P1 2.854(5) 7_665 ? C2 C4 1.513(6) . ? C3 C4 1.543(6) . ? C4 C5 1.541(5) . ? C5 C6 1.399(5) . ? C7 C12 1.383(5) . ? C7 C8 1.390(5) . ? C8 C9 1.380(5) . ? C9 C10 1.383(6) . ? C10 C11 1.363(6) . ? C11 C12 1.379(5) . ? C13 C18 1.383(5) . ? C13 C14 1.393(5) . ? C14 C15 1.380(5) . ? C15 C16 1.378(6) . ? C16 C17 1.370(6) . ? C17 C18 1.384(5) . ? C50 C51 0.32(4) 4 ? C50 C55 0.52(5) 3 ? C50 C53 0.62(3) 2 ? C50 C54 0.93(2) 3 ? C50 C52 1.04(6) 2 ? C50 C52 1.08(2) 4 ? C50 C54 1.38(6) 2 ? C50 C51 1.39 . ? C50 C55 1.39 . ? C50 C50 1.55(2) 4 ? C50 C50 1.55(2) 3 ? C50 C51 1.82(4) 2 ? C51 C50 0.32(3) 3 ? C51 C54 0.63(4) 2 ? C51 C52 0.73(5) 4 ? C51 C53 0.75(2) 4 ? C51 C55 0.83(5) 2 ? C51 C55 1.15(2) 3 ? C51 C52 1.39 . ? C51 C53 1.65(6) 2 ? C51 C51 1.68(3) 3 ? C51 C51 1.68(4) 4 ? C51 C54 1.70(2) 4 ? C52 C54 0.35(2) 4 ? C52 C55 0.63(5) 2 ? C52 C51 0.73(3) 3 ? C52 C50 1.04(4) 2 ? C52 C53 1.07(5) 4 ? C52 C50 1.08(2) 3 ? C52 C53 1.39 . ? C52 C55 1.55(2) 4 ? C52 C54 1.99(5) 2 ? C53 C55 0.51(4) 4 ? C53 C50 0.62(3) 2 ? C53 C51 0.75(3) 3 ? C53 C52 1.07(4) 3 ? C53 C54 1.15(4) 4 ? C53 C54 1.39 . ? C53 C51 1.65(5) 2 ? C53 C55 1.88(5) 2 ? C53 C50 1.89(3) 4 ? C54 C52 0.35(3) 3 ? C54 C51 0.63(5) 2 ? C54 C50 0.93(2) 4 ? C54 C55 0.94(3) 4 ? C54 C53 1.15(5) 3 ? C54 C50 1.38(4) 2 ? C54 C55 1.39 . ? C54 C51 1.70(2) 3 ? C54 C52 1.99(5) 2 ? C55 C53 0.51(2) 3 ? C55 C50 0.52(2) 4 ? C55 C52 0.63(6) 2 ? C55 C51 0.83(5) 2 ? C55 C54 0.94(5) 3 ? C55 C51 1.15(2) 4 ? C55 C52 1.55(2) 3 ? C55 C53 1.88(6) 2 ? C55 C55 1.90(5) 3 ? C55 C55 1.90(4) 4 ? 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 P1 C6 118.72(14) . . ? O1 P1 C7 108.93(14) . . ? C6 P1 C7 107.0(2) . . ? O1 P1 C13 107.35(13) . . ? C6 P1 C13 110.8(2) . . ? C7 P1 C13 102.84(14) . . ? O1 P1 Li1 42.76(13) . 8_655 ? C6 P1 Li1 82.4(2) . 8_655 ? C7 P1 Li1 146.6(2) . 8_655 ? C13 P1 Li1 103.38(15) . 8_655 ? P1 O1 Li1 143.4(2) . . ? P1 O1 Li1 106.3(2) . 8_655 ? Li1 O1 Li1 85.2(2) . 8_655 ? P1 O1 Li1 129.5(2) . 7_665 ? Li1 O1 Li1 85.1(2) . 7_665 ? Li1 O1 Li1 85.6(2) 8_655 7_665 ? C5 N1 Li1 119.2(3) . 8_655 ? O1 Li1 N1 131.5(3) . 7_665 ? O1 Li1 O1 94.7(2) . 7_665 ? N1 Li1 O1 103.7(3) 7_665 7_665 ? O1 Li1 O1 94.6(2) . 8_655 ? N1 Li1 O1 127.4(3) 7_665 8_655 ? O1 Li1 O1 94.2(2) 7_665 8_655 ? O1 Li1 Li1 48.5(2) . 8_655 ? N1 Li1 Li1 162.6(3) 7_665 8_655 ? O1 Li1 Li1 93.3(2) 7_665 8_655 ? O1 Li1 Li1 46.35(14) 8_655 8_655 ? O1 Li1 Li1 48.5(2) . 7_665 ? N1 Li1 Li1 134.1(3) 7_665 7_665 ? O1 Li1 Li1 46.35(14) 7_665 7_665 ? O1 Li1 Li1 93.3(2) 8_655 7_665 ? Li1 Li1 Li1 61.4(2) 8_655 7_665 ? O1 Li1 Li1 93.1(2) . 2_655 ? N1 Li1 Li1 131.9(2) 7_665 2_655 ? O1 Li1 Li1 47.2(2) 7_665 2_655 ? O1 Li1 Li1 47.2(2) 8_655 2_655 ? Li1 Li1 Li1 59.29(11) 8_655 2_655 ? Li1 Li1 Li1 59.29(11) 7_665 2_655 ? O1 Li1 P1 117.6(2) . 7_665 ? N1 Li1 P1 72.9(2) 7_665 7_665 ? O1 Li1 P1 30.93(10) 7_665 7_665 ? O1 Li1 P1 110.8(2) 8_655 7_665 ? Li1 Li1 P1 123.8(2) 8_655 7_665 ? Li1 Li1 P1 73.2(2) 7_665 7_665 ? Li1 Li1 P1 70.1(2) 2_655 7_665 ? C1 C4 C2 110.9(4) . . ? C1 C4 C5 113.8(3) . . ? C2 C4 C5 108.8(3) . . ? C1 C4 C3 106.5(4) . . ? C2 C4 C3 106.9(4) . . ? C5 C4 C3 109.7(3) . . ? N1 C5 C6 119.4(3) . . ? N1 C5 C4 120.4(3) . . ? C6 C5 C4 120.3(3) . . ? C5 C6 P1 120.8(3) . . ? C12 C7 C8 118.9(3) . . ? C12 C7 P1 120.8(3) . . ? C8 C7 P1 120.3(3) . . ? C9 C8 C7 120.3(4) . . ? C8 C9 C10 119.8(4) . . ? C11 C10 C9 120.2(4) . . ? C10 C11 C12 120.2(4) . . ? C11 C12 C7 120.6(4) . . ? C18 C13 C14 118.4(3) . . ? C18 C13 P1 120.2(3) . . ? C14 C13 P1 121.1(3) . . ? C15 C14 C13 120.2(4) . . ? C16 C15 C14 120.5(4) . . ? C17 C16 C15 119.8(4) . . ? C16 C17 C18 119.9(4) . . ? C13 C18 C17 121.0(4) . . ? C51 C50 C55 153.9(54) 4 3 ? C51 C50 C53 101.1(100) 4 2 ? C55 C50 C53 52.9(83) 3 2 ? C51 C50 C54 18.2(45) 4 3 ? C55 C50 C54 144.8(47) 3 3 ? C53 C50 C54 94.1(43) 2 3 ? C51 C50 C52 13.0(35) 4 2 ? C55 C50 C52 163.9(44) 3 2 ? C53 C50 C52 111.5(61) 2 2 ? C54 C50 C52 19.4(20) 3 2 ? C51 C50 C52 161.8(17) 4 4 ? C55 C50 C52 23.4(30) 3 4 ? C53 C50 C52 72.7(46) 2 4 ? C54 C50 C52 166.8(16) 3 4 ? C52 C50 C52 170.1(13) 2 4 ? C51 C50 C54 169.3(19) 4 2 ? C55 C50 C54 26.3(27) 3 2 ? C53 C50 C54 78.4(56) 2 2 ? C54 C50 C54 170.4(20) 3 2 ? C52 C50 C54 169.8(28) 2 2 ? C52 C50 C54 8.7(9) 4 2 ? C51 C50 C51 149.7(48) 4 . ? C55 C50 C51 52.6(24) 3 . ? C53 C50 C51 103.9(72) 2 . ? C54 C50 C51 162.0(32) 3 . ? C52 C50 C51 143.5(24) 2 . ? C52 C50 C51 31.2(26) 4 . ? C54 C50 C51 26.3(22) 2 . ? C51 C50 C55 37.4(43) 4 . ? C55 C50 C55 167.2(18) 3 . ? C53 C50 C55 136.1(72) 2 . ? C54 C50 C55 42.0(32) 3 . ? C52 C50 C55 25.3(24) 2 . ? C52 C50 C55 151.2(27) 4 . ? C54 C50 C55 145.3(22) 2 . ? C51 C50 C55 120.0 . . ? C51 C50 C50 54.7(42) 4 4 ? C55 C50 C50 151.5(20) 3 4 ? C53 C50 C50 155.4(79) 2 4 ? C54 C50 C50 61.5(39) 3 4 ? C52 C50 C50 43.9(28) 2 4 ? C52 C50 C50 131.6(33) 4 4 ? C54 C50 C50 126.2(26) 2 4 ? C51 C50 C50 100.5(9) . 4 ? C55 C50 C50 19.5(9) . 4 ? C51 C50 C50 141.6(44) 4 3 ? C55 C50 C50 62.5(21) 3 3 ? C53 C50 C50 114.6(79) 2 3 ? C54 C50 C50 151.2(39) 3 3 ? C52 C50 C50 133.5(28) 2 3 ? C52 C50 C50 42.0(33) 4 3 ? C54 C50 C50 36.3(25) 2 3 ? C51 C50 C50 11.0(10) . 3 ? C55 C50 C50 109.4(9) . 3 ? C50 C50 C50 90.0 4 3 ? C51 C50 C51 59.8(47) 4 2 ? C55 C50 C51 146.1(30) 3 2 ? C53 C50 C51 160.9(69) 2 2 ? C54 C50 C51 67.5(30) 3 2 ? C52 C50 C51 49.6(17) 2 2 ? C52 C50 C51 125.5(27) 4 2 ? C54 C50 C51 120.4(22) 2 2 ? C51 C50 C51 94.5(13) . 2 ? C55 C50 C51 25.8(13) . 2 ? C50 C50 C51 6.4(12) 4 2 ? C50 C50 C51 84.1(12) 3 2 ? C50 C51 C54 152.5(79) 3 2 ? C50 C51 C52 161.3(55) 3 4 ? C54 C51 C52 28.7(59) 2 4 ? C50 C51 C53 53.7(69) 3 4 ? C54 C51 C53 112.8(35) 2 4 ? C52 C51 C53 140.3(47) 4 4 ? C50 C51 C55 16.2(38) 3 2 ? C54 C51 C55 144.9(55) 2 2 ? C52 C51 C55 170.9(13) 4 2 ? C53 C51 C55 37.7(37) 4 2 ? C50 C51 C55 132.7(60) 3 3 ? C54 C51 C55 54.4(38) 2 3 ? C52 C51 C55 29.9(25) 4 3 ? C53 C51 C55 164.6(15) 4 3 ? C55 C51 C55 148.4(33) 2 3 ? C50 C51 C52 14.0(70) 3 . ? C54 C51 C52 160.4(53) 2 . ? C52 C51 C52 169.9(17) 4 . ? C53 C51 C52 49.8(38) 4 . ? C55 C51 C52 15.5(21) 2 . ? C55 C51 C52 140.6(24) 3 . ? C50 C51 C50 114.4(42) 3 . ? C54 C51 C50 75.6(61) 2 . ? C52 C51 C50 50.1(17) 4 . ? C53 C51 C50 167.3(31) 4 . ? C55 C51 C50 130.6(25) 2 . ? C55 C51 C50 21.2(24) 3 . ? C52 C51 C50 120.0 . . ? C50 C51 C53 134.9(53) 3 2 ? C54 C51 C53 55.1(43) 2 2 ? C52 C51 C53 28.9(20) 4 2 ? C53 C51 C53 167.5(24) 4 2 ? C55 C51 C53 151.0(33) 2 2 ? C55 C51 C53 4.94(11) 3 2 ? C52 C51 C53 141.2(21) . 2 ? C50 C51 C53 21.2(21) . 2 ? C50 C51 C51 24.7(47) 3 3 ? C54 C51 C51 164.9(36) 2 3 ? C52 C51 C51 144.7(15) 4 3 ? C53 C51 C51 74.9(42) 4 3 ? C55 C51 C51 38.3(26) 2 3 ? C55 C51 C51 115.5(27) 3 3 ? C52 C51 C51 25.3(7) . 3 ? C50 C51 C51 94.7(7) . 3 ? C53 C51 C51 115.9(23) 2 3 ? C50 C51 C51 110.6(35) 3 4 ? C54 C51 C51 80.9(65) 2 4 ? C52 C51 C51 54.7(15) 4 4 ? C53 C51 C51 164.3(41) 4 4 ? C55 C51 C51 126.7(25) 2 4 ? C55 C51 C51 26.5(27) 3 4 ? C52 C51 C51 115.3(7) . 4 ? C50 C51 C51 5.6(6) . 4 ? C53 C51 C51 26.0(23) 2 4 ? C51 C51 C51 90.0 3 4 ? C50 C51 C54 8.7(73) 3 4 ? C54 C51 C54 160.0(36) 2 4 ? C52 C51 C54 165.3(27) 4 4 ? C53 C51 C54 53.7(26) 4 4 ? C55 C51 C54 16.9(16) 2 4 ? C55 C51 C54 135.4(20) 3 4 ? C52 C51 C54 6.4(10) . 4 ? C50 C51 C54 115.4(14) . 4 ? C53 C51 C54 136.6(20) 2 4 ? C51 C51 C54 21.5(18) 3 4 ? C51 C51 C54 111.0(18) 4 4 ? C54 C52 C55 142.8(23) 4 2 ? C54 C52 C51 59.6(88) 4 3 ? C55 C52 C51 115.1(37) 2 3 ? C54 C52 C50 61.8(73) 4 2 ? C55 C52 C50 109.9(40) 2 2 ? C51 C52 C50 5.7(22) 3 2 ? C54 C52 C53 151.9(34) 4 4 ? C55 C52 C53 18.8(18) 2 4 ? C51 C52 C53 132.0(18) 3 4 ? C50 C52 C53 127.3(20) 2 4 ? C54 C52 C50 143.7(50) 4 3 ? C55 C52 C50 19.2(25) 2 3 ? C51 C52 C50 98.7(29) 3 3 ? C50 C52 C50 94.2(27) 2 3 ? C53 C52 C50 33.3(12) 4 3 ? C54 C52 C51 147.5(45) 4 . ? C55 C52 C51 20.5(28) 2 . ? C51 C52 C51 100.0(24) 3 . ? C50 C52 C51 95.7(16) 2 . ? C53 C52 C51 32.3(13) 4 . ? C50 C52 C51 4.2(22) 3 . ? C54 C52 C53 41.2(65) 4 . ? C55 C52 C53 133.5(30) 2 . ? C51 C52 C53 20.1(24) 3 . ? C50 C52 C53 24.3(16) 2 . ? C53 C52 C53 151.5(13) 4 . ? C50 C52 C53 118.5(13) 3 . ? C51 C52 C53 120.0 . . ? C54 C52 C55 56.6(58) 4 4 ? C55 C52 C55 114.7(38) 2 4 ? C51 C52 C55 4.9(7) 3 4 ? C50 C52 C55 5.4(18) 2 4 ? C53 C52 C55 132.4(23) 4 4 ? C50 C52 C55 99.3(22) 3 4 ? C51 C52 C55 101.0(13) . 4 ? C53 C52 C55 19.1(13) . 4 ? C54 C52 C54 147.6(35) 4 2 ? C55 C52 C54 14.4(17) 2 2 ? C51 C52 C54 104.8(35) 3 2 ? C50 C52 C54 100.3(26) 2 2 ? C53 C52 C54 27.2(18) 4 2 ? C50 C52 C54 6.1(13) 3 2 ? C51 C52 C54 6.1(15) . 2 ? C53 C52 C54 124.6(17) . 2 ? C55 C52 C54 105.4(19) 4 2 ? C55 C53 C50 54.4(42) 4 2 ? C55 C53 C51 79.5(39) 4 3 ? C50 C53 C51 25.1(32) 2 3 ? C55 C53 C52 23.3(20) 4 3 ? C50 C53 C52 74.0(28) 2 3 ? C51 C53 C52 98.0(27) 3 3 ? C55 C53 C54 107.0(31) 4 4 ? C50 C53 C54 53.6(26) 2 4 ? C51 C53 C54 30.3(19) 3 4 ? C52 C53 C54 127.6(8) 3 4 ? C55 C53 C54 22.5(23) 4 . ? C50 C53 C54 75.9(33) 2 . ? C51 C53 C54 100.6(18) 3 . ? C52 C53 C54 6.8(5) 3 . ? C54 C53 C54 129.2(13) 4 . ? C55 C53 C52 98.4(24) 4 . ? C50 C53 C52 44.2(33) 2 . ? C51 C53 C52 19.6(18) 3 . ? C52 C53 C52 117.5(15) 3 . ? C54 C53 C52 11.6(11) 4 . ? C54 C53 C52 120.0 . . ? C55 C53 C51 11.1(7) 4 2 ? C50 C53 C51 54.8(26) 2 2 ? C51 C53 C51 79.1(24) 3 2 ? C52 C53 C51 19.2(16) 3 2 ? C54 C53 C51 108.5(17) 4 2 ? C54 C53 C51 21.8(13) . 2 ? C52 C53 C51 98.6(13) . 2 ? C55 C53 C55 84.7(30) 4 2 ? C50 C53 C55 30.8(24) 2 2 ? C51 C53 C55 9.3(8) 3 2 ? C52 C53 C55 104.8(21) 3 2 ? C54 C53 C55 22.8(16) 4 2 ? C54 C53 C55 106.6(14) . 2 ? C52 C53 C55 14.1(13) . 2 ? C51 C53 C55 85.7(13) 2 2 ? C55 C53 C50 10.5(16) 4 4 ? C50 C53 C50 48.2(34) 2 4 ? C51 C53 C50 72.7(23) 3 4 ? C52 C53 C50 25.9(14) 3 4 ? C54 C53 C50 101.8(15) 4 4 ? C54 C53 C50 27.8(6) . 4 ? C52 C53 C50 92.2(6) . 4 ? C51 C53 C50 7.0(10) 2 4 ? C55 C53 C50 79.0(17) 2 4 ? C52 C54 C51 91.7(67) 3 2 ? C52 C54 C50 98.7(53) 3 4 ? C51 C54 C50 9.3(24) 2 4 ? C52 C54 C55 24.1(32) 3 4 ? C51 C54 C55 92.5(24) 2 4 ? C50 C54 C55 96.4(25) 4 4 ? C52 C54 C53 127.2(44) 3 3 ? C51 C54 C53 36.9(22) 2 3 ? C50 C54 C53 32.3(14) 4 3 ? C55 C54 C53 128.7(11) 4 3 ? C52 C54 C50 27.6(41) 3 2 ? C51 C54 C50 78.1(34) 2 2 ? C50 C54 C50 82.2(24) 4 2 ? C55 C54 C50 14.4(15) 4 2 ? C53 C54 C50 114.4(15) 3 2 ? C52 C54 C53 21.3(22) 3 . ? C51 C54 C53 103.1(34) 2 . ? C50 C54 C53 107.8(15) 4 . ? C55 C54 C53 12.1(17) 4 . ? C53 C54 C53 139.8(12) 3 . ? C50 C54 C53 25.7(12) 2 . ? C52 C54 C55 111.2(40) 3 . ? C51 C54 C55 20.0(29) 2 . ? C50 C54 C55 12.6(15) 4 . ? C55 C54 C55 108.4(18) 4 . ? C53 C54 C55 20.7(12) 3 . ? C50 C54 C55 94.3(12) 2 . ? C53 C54 C55 120.0 . . ? C52 C54 C51 26.1(34) 3 3 ? C51 C54 C51 77.7(42) 2 3 ? C50 C54 C51 82.1(22) 4 3 ? C55 C54 C51 14.9(23) 4 3 ? C53 C54 C51 114.2(21) 3 3 ? C50 C54 C51 2.0(18) 2 3 ? C53 C54 C51 25.7(11) . 3 ? C55 C54 C51 94.3(11) . 3 ? C52 C54 C52 105.0(46) 3 2 ? C51 C54 C52 13.5(30) 2 2 ? C50 C54 C52 7.1(12) 4 2 ? C55 C54 C52 103.5(27) 4 2 ? C53 C54 C52 25.2(17) 3 2 ? C50 C54 C52 89.2(20) 2 2 ? C53 C54 C52 114.8(16) . 2 ? C55 C54 C52 6.5(11) . 2 ? C51 C54 C52 89.1(17) 3 2 ? C53 C55 C50 72.7(67) 3 4 ? C53 C55 C52 137.9(33) 3 2 ? C50 C55 C52 137.4(45) 4 2 ? C53 C55 C51 62.9(62) 3 2 ? C50 C55 C51 9.9(23) 4 2 ? C52 C55 C51 144.0(46) 2 2 ? C53 C55 C54 145.3(58) 3 3 ? C50 C55 C54 139.3(19) 4 3 ? C52 C55 C54 13.1(19) 2 3 ? C51 C55 C54 148.1(29) 2 3 ? C53 C55 C51 164.0(4) 3 4 ? C50 C55 C51 106.2(35) 4 4 ? C52 C55 C51 35.0(24) 2 4 ? C51 C55 C51 115.1(40) 2 4 ? C54 C55 C51 33.1(22) 3 4 ? C53 C55 C54 52.3(52) 3 . ? C50 C55 C54 22.7(24) 4 . ? C52 C55 C54 159.0(29) 2 . ? C51 C55 C54 15.1(19) 2 . ? C54 C55 C54 161.6(13) 3 . ? C51 C55 C54 128.6(21) 4 . ? C53 C55 C50 165.7(29) 3 . ? C50 C55 C50 98.0(23) 4 . ? C52 C55 C50 44.7(44) 2 . ? C51 C55 C50 107.3(24) 2 . ? C54 C55 C50 41.6(13) 3 . ? C51 C55 C50 9.9(19) 4 . ? C54 C55 C50 120.0 . . ? C53 C55 C52 62.4(42) 3 3 ? C50 C55 C52 10.7(28) 4 3 ? C52 C55 C52 147.2(35) 2 3 ? C51 C55 C52 4.3(9) 2 3 ? C54 C55 C52 150.0(25) 3 3 ? C51 C55 C52 116.9(21) 4 3 ? C54 C55 C52 12.1(13) . 3 ? C50 C55 C52 108.6(14) . 3 ? C53 C55 C53 167.4(17) 3 2 ? C50 C55 C53 111.0(28) 4 2 ? C52 C55 C53 32.4(28) 2 2 ? C51 C55 C53 120.2(35) 2 2 ? C54 C55 C53 28.5(19) 3 2 ? C51 C55 C53 6.1(5) 4 2 ? C54 C55 C53 133.1(19) . 2 ? C50 C55 C53 13.1(19) . 2 ? C52 C55 C53 121.7(19) 3 2 ? C53 C55 C55 166.2(42) 3 3 ? C50 C55 C55 96.0(17) 4 3 ? C52 C55 C55 47.7(45) 2 3 ? C51 C55 C55 105.6(21) 2 3 ? C54 C55 C55 43.8(11) 3 3 ? C51 C55 C55 13.1(20) 4 3 ? C54 C55 C55 117.8(6) . 3 ? C50 C55 C55 3.5(4) . 3 ? C52 C55 C55 106.6(17) 3 3 ? C53 C55 C55 15.6(19) 2 3 ? C53 C55 C55 79.7(56) 3 4 ? C50 C55 C55 9.3(29) 4 4 ? C52 C55 C55 134.6(41) 2 4 ? C51 C55 C55 18.4(19) 2 4 ? C54 C55 C55 133.8(11) 3 4 ? C51 C55 C55 101.1(23) 4 4 ? C54 C55 C55 27.8(6) . 4 ? C50 C55 C55 92.3(6) . 4 ? C52 C55 C55 17.6(16) 3 4 ? C53 C55 C55 105.4(19) 2 4 ? C55 C55 C55 90.0 3 4 ? _refine_diff_density_max 0.629 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.062 data_rs9818 #compound 3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H29 Li N2 O P' _chemical_formula_weight 363.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Li' 'Li' -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 '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/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.740(6) _cell_length_b 9.803(2) _cell_length_c 20.206(4) _cell_angle_alpha 90.00 _cell_angle_beta 130.69(3) _cell_angle_gamma 90.00 _cell_volume 4166.6(14) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.159 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1560 _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_type Psi-Scans _exptl_absorpt_correction_T_min 0.9652 _exptl_absorpt_correction_T_max 0.9720 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7372 _diffrn_reflns_av_R_equivalents 0.1087 _diffrn_reflns_av_sigmaI/netI 0.1364 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3669 _reflns_number_gt 1998 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0502P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3669 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1363 _refine_ls_R_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.1464 _refine_ls_wR_factor_gt 0.1201 _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_restrained_S_all 0.960 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.11287(5) 0.05654(10) 0.28495(7) 0.0256(3) Uani 1 1 d . . . O1 O 0.04954(11) 0.1271(2) 0.23910(16) 0.0278(6) Uani 1 1 d . . . N1 N 0.07228(15) -0.1026(3) 0.3624(2) 0.0321(8) Uani 1 1 d . . . C1 C 0.16357(18) 0.1559(4) 0.2763(2) 0.0277(9) Uani 1 1 d . . . Li1 Li 0.0000 0.2447(9) 0.2500 0.036(2) Uani 1 2 d S . . C2 C 0.22772(18) 0.1253(4) 0.3262(3) 0.0344(10) Uani 1 1 d . . . H2A H 0.2458 0.0525 0.3670 0.041 Uiso 1 1 calc R . . N2 N 0.05166(16) 0.3984(3) 0.3440(2) 0.0398(9) Uani 1 1 d . . . Li2 Li 0.0000 -0.0162(9) 0.2500 0.030(2) Uani 1 2 d S . . C3 C 0.2655(2) 0.1990(4) 0.3173(3) 0.0415(11) Uani 1 1 d . . . H3A H 0.3093 0.1769 0.3522 0.050 Uiso 1 1 calc R . . C4 C 0.2404(2) 0.3040(4) 0.2583(3) 0.0415(11) Uani 1 1 d . . . H4A H 0.2667 0.3554 0.2529 0.050 Uiso 1 1 calc R . . C5 C 0.1767(2) 0.3346(4) 0.2071(3) 0.0412(11) Uani 1 1 d . . . H5A H 0.1588 0.4060 0.1654 0.049 Uiso 1 1 calc R . . C6 C 0.1384(2) 0.2612(4) 0.2163(3) 0.0353(10) Uani 1 1 d . . . H6A H 0.0946 0.2834 0.1811 0.042 Uiso 1 1 calc R . . C7 C 0.09532(16) -0.0948(4) 0.2201(2) 0.0244(8) Uani 1 1 d . . . C8 C 0.04983(19) -0.0867(4) 0.1289(3) 0.0350(10) Uani 1 1 d . . . H8A H 0.0278 -0.0035 0.1020 0.042 Uiso 1 1 calc R . . C9 C 0.0367(2) -0.1977(4) 0.0780(3) 0.0413(11) Uani 1 1 d . . . H9A H 0.0064 -0.1905 0.0162 0.050 Uiso 1 1 calc R . . C10 C 0.06778(19) -0.3200(4) 0.1169(3) 0.0374(11) Uani 1 1 d . . . H10A H 0.0584 -0.3975 0.0820 0.045 Uiso 1 1 calc R . . C11 C 0.11217(19) -0.3287(4) 0.2060(3) 0.0356(10) Uani 1 1 d . . . H11A H 0.1337 -0.4125 0.2326 0.043 Uiso 1 1 calc R . . C12 C 0.12613(18) -0.2179(4) 0.2576(3) 0.0304(9) Uani 1 1 d . . . H12A H 0.1571 -0.2258 0.3193 0.036 Uiso 1 1 calc R . . C13 C 0.15792(17) 0.0182(4) 0.3930(2) 0.0275(9) Uani 1 1 d . . . H13A H 0.2006 0.0493 0.4340 0.033 Uiso 1 1 calc R . . C14 C 0.13155(16) -0.0596(4) 0.4211(2) 0.0249(8) Uani 1 1 d . . . C15 C 0.17167(17) -0.0945(4) 0.5180(2) 0.0287(9) Uani 1 1 d . . . C16 C 0.1790(2) -0.2509(4) 0.5278(3) 0.0469(12) Uani 1 1 d . . . H16A H 0.1998 -0.2835 0.5060 0.070 Uiso 1 1 calc R . . H16B H 0.1370 -0.2932 0.4942 0.070 Uiso 1 1 calc R . . H16C H 0.2050 -0.2754 0.5895 0.070 Uiso 1 1 calc R . . C17 C 0.1371(2) -0.0445(5) 0.5494(3) 0.0412(11) Uani 1 1 d . . . H17A H 0.1307 0.0543 0.5409 0.062 Uiso 1 1 calc R . . H17B H 0.1627 -0.0659 0.6115 0.062 Uiso 1 1 calc R . . H17C H 0.0958 -0.0902 0.5159 0.062 Uiso 1 1 calc R . . C18 C 0.23789(18) -0.0314(5) 0.5765(3) 0.0442(12) Uani 1 1 d . . . H18A H 0.2343 0.0681 0.5702 0.066 Uiso 1 1 calc R . . H18B H 0.2616 -0.0659 0.5595 0.066 Uiso 1 1 calc R . . H18C H 0.2604 -0.0558 0.6374 0.066 Uiso 1 1 calc R . . C19 C 0.0572(3) 0.3789(6) 0.4205(4) 0.087(2) Uani 1 1 d . . . H19A H 0.0785 0.4580 0.4593 0.130 Uiso 1 1 calc R . . H19B H 0.0820 0.2964 0.4518 0.130 Uiso 1 1 calc R . . H19C H 0.0147 0.3693 0.4018 0.130 Uiso 1 1 calc R . . C20 C 0.1156(2) 0.4087(5) 0.3739(3) 0.0583(14) Uani 1 1 d . . . H20A H 0.1377 0.4866 0.4136 0.087 Uiso 1 1 calc R . . H20B H 0.1130 0.4216 0.3236 0.087 Uiso 1 1 calc R . . H20C H 0.1392 0.3248 0.4046 0.087 Uiso 1 1 calc R . . C21 C 0.0141(3) 0.5196(5) 0.2962(3) 0.0700(16) Uani 1 1 d . . . H21A H 0.0415 0.6012 0.3255 0.105 Uiso 1 1 calc R . . H21B H -0.0205 0.5268 0.2983 0.105 Uiso 1 1 calc R . . H1 H 0.0622(15) -0.151(3) 0.386(2) 0.012(9) 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 P1 0.0274(5) 0.0258(5) 0.0301(6) 0.0016(5) 0.0215(5) 0.0012(5) O1 0.0276(14) 0.0274(14) 0.0331(15) 0.0002(12) 0.0219(13) 0.0026(11) N1 0.035(2) 0.038(2) 0.030(2) 0.0021(16) 0.0240(18) -0.0032(16) C1 0.033(2) 0.024(2) 0.037(2) -0.0030(18) 0.028(2) -0.0020(18) Li1 0.044(6) 0.025(5) 0.051(6) 0.000 0.037(5) 0.000 C2 0.035(2) 0.038(2) 0.042(3) 0.001(2) 0.030(2) 0.002(2) N2 0.045(2) 0.039(2) 0.046(2) -0.0072(18) 0.035(2) -0.0059(18) Li2 0.031(5) 0.030(5) 0.032(5) 0.000 0.022(5) 0.000 C3 0.035(3) 0.051(3) 0.050(3) -0.010(2) 0.032(2) -0.010(2) C4 0.061(3) 0.036(3) 0.059(3) -0.020(2) 0.053(3) -0.019(2) C5 0.070(3) 0.025(2) 0.058(3) -0.001(2) 0.054(3) -0.004(2) C6 0.045(3) 0.035(2) 0.044(3) 0.003(2) 0.037(2) 0.005(2) C7 0.026(2) 0.023(2) 0.031(2) 0.0027(17) 0.0215(19) 0.0015(16) C8 0.046(3) 0.029(2) 0.036(2) 0.0034(19) 0.029(2) 0.0080(19) C9 0.043(3) 0.047(3) 0.030(2) 0.000(2) 0.022(2) 0.003(2) C10 0.044(3) 0.040(3) 0.047(3) -0.016(2) 0.037(3) -0.007(2) C11 0.036(2) 0.027(2) 0.045(3) 0.005(2) 0.027(2) 0.0053(19) C12 0.033(2) 0.030(2) 0.032(2) -0.0002(19) 0.023(2) 0.0022(18) C13 0.023(2) 0.030(2) 0.028(2) -0.0028(17) 0.0155(19) -0.0019(17) C14 0.025(2) 0.0244(19) 0.028(2) -0.0021(18) 0.0184(18) 0.0045(17) C15 0.030(2) 0.031(2) 0.023(2) -0.0009(17) 0.0165(19) 0.0050(18) C16 0.061(3) 0.037(3) 0.035(3) 0.009(2) 0.028(2) 0.010(2) C17 0.046(3) 0.050(3) 0.035(2) -0.002(2) 0.029(2) 0.001(2) C18 0.032(2) 0.063(3) 0.028(2) -0.005(2) 0.016(2) -0.001(2) C19 0.098(5) 0.118(5) 0.067(4) -0.024(4) 0.064(4) -0.043(4) C20 0.056(3) 0.055(3) 0.078(4) -0.032(3) 0.050(3) -0.022(3) C21 0.080(4) 0.037(3) 0.076(4) -0.015(3) 0.043(4) 0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.517(3) . ? P1 C13 1.706(4) . ? P1 C1 1.810(4) . ? P1 C7 1.823(4) . ? P1 Li2 2.816(2) . ? O1 Li1 1.913(6) . ? O1 Li2 2.075(6) . ? N1 C14 1.321(5) . ? N1 Li2 1.990(5) . ? C1 C6 1.385(5) . ? C1 C2 1.391(5) . ? Li1 O1 1.913(6) 2 ? Li1 N2 2.094(7) . ? Li1 N2 2.094(7) 2 ? Li1 Li2 2.558(13) . ? C2 C3 1.378(5) . ? N2 C21 1.456(5) . ? N2 C20 1.459(5) . ? N2 C19 1.463(6) . ? Li2 N1 1.990(5) 2 ? Li2 O1 2.075(6) 2 ? Li2 P1 2.816(2) 2 ? C3 C4 1.372(6) . ? C4 C5 1.378(6) . ? C5 C6 1.390(5) . ? C7 C12 1.384(5) . ? C7 C8 1.400(5) . ? C8 C9 1.373(5) . ? C9 C10 1.383(5) . ? C10 C11 1.369(5) . ? C11 C12 1.375(5) . ? C13 C14 1.408(5) . ? C14 C15 1.532(5) . ? C15 C18 1.524(5) . ? C15 C17 1.535(5) . ? C15 C16 1.543(5) . ? C21 C21 1.480(10) 2 ? 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 P1 C13 118.19(16) . . ? O1 P1 C1 111.04(16) . . ? C13 P1 C1 105.93(18) . . ? O1 P1 C7 105.78(16) . . ? C13 P1 C7 111.72(17) . . ? C1 P1 C7 103.24(16) . . ? O1 P1 Li2 46.10(18) . . ? C13 P1 Li2 91.86(14) . . ? C1 P1 Li2 156.77(19) . . ? C7 P1 Li2 83.19(18) . . ? P1 O1 Li1 146.85(17) . . ? P1 O1 Li2 102.11(19) . . ? Li1 O1 Li2 79.7(3) . . ? C14 N1 Li2 128.8(3) . . ? C6 C1 C2 118.1(3) . . ? C6 C1 P1 120.4(3) . . ? C2 C1 P1 121.4(3) . . ? O1 Li1 O1 105.9(4) . 2 ? O1 Li1 N2 114.84(13) . . ? O1 Li1 N2 116.56(13) 2 . ? O1 Li1 N2 116.56(13) . 2 ? O1 Li1 N2 114.84(13) 2 2 ? N2 Li1 N2 88.0(4) . 2 ? O1 Li1 Li2 52.9(2) . . ? O1 Li1 Li2 52.9(2) 2 . ? N2 Li1 Li2 136.0(2) . . ? N2 Li1 Li2 136.0(2) 2 . ? C3 C2 C1 121.0(4) . . ? C21 N2 C20 111.7(4) . . ? C21 N2 C19 110.2(4) . . ? C20 N2 C19 108.1(4) . . ? C21 N2 Li1 102.4(3) . . ? C20 N2 Li1 110.7(3) . . ? C19 N2 Li1 113.8(3) . . ? N1 Li2 N1 129.6(5) 2 . ? N1 Li2 O1 114.28(15) 2 . ? N1 Li2 O1 99.52(14) . . ? N1 Li2 O1 99.52(14) 2 2 ? N1 Li2 O1 114.28(15) . 2 ? O1 Li2 O1 94.8(4) . 2 ? N1 Li2 Li1 115.2(2) 2 . ? N1 Li2 Li1 115.2(2) . . ? O1 Li2 Li1 47.38(19) . . ? O1 Li2 Li1 47.38(19) 2 . ? N1 Li2 P1 121.48(11) 2 . ? N1 Li2 P1 72.15(10) . . ? O1 Li2 P1 31.79(7) . . ? O1 Li2 P1 120.5(3) 2 . ? Li1 Li2 P1 75.33(17) . . ? N1 Li2 P1 72.15(10) 2 2 ? N1 Li2 P1 121.48(11) . 2 ? O1 Li2 P1 120.5(3) . 2 ? O1 Li2 P1 31.79(7) 2 2 ? Li1 Li2 P1 75.33(17) . 2 ? P1 Li2 P1 150.7(3) . 2 ? C4 C3 C2 120.5(4) . . ? C3 C4 C5 119.5(4) . . ? C4 C5 C6 120.2(4) . . ? C1 C6 C5 120.7(4) . . ? C12 C7 C8 118.4(3) . . ? C12 C7 P1 122.4(3) . . ? C8 C7 P1 119.3(3) . . ? C9 C8 C7 120.8(4) . . ? C8 C9 C10 119.9(4) . . ? C11 C10 C9 119.6(4) . . ? C10 C11 C12 121.0(4) . . ? C11 C12 C7 120.3(4) . . ? C14 C13 P1 119.7(3) . . ? N1 C14 C13 118.7(3) . . ? N1 C14 C15 121.2(3) . . ? C13 C14 C15 120.1(3) . . ? C18 C15 C14 113.9(3) . . ? C18 C15 C17 108.2(3) . . ? C14 C15 C17 109.1(3) . . ? C18 C15 C16 108.2(3) . . ? C14 C15 C16 108.2(3) . . ? C17 C15 C16 109.2(3) . . ? N2 C21 C21 113.5(3) . 2 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.232 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.058