# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 182/1416 data_total _audit_creation_method SHELXL-97 _publ_contact_author_name 'Carlo Floriani' _publ_contact_author_address ; Institut de Chimie Min\'erale et Analytique BCH # 3307 Universit\'e de Lausanne CH-1015 Lausanne Switzerland ; _publ_contact_author_email 'carlo.floriani@icma.unil.ch' _publ_contact_author_fax '+4121 692 3905' _publ_contact_author_phone '+4121 692 3902' _publ_section_title ; Porphodimethene-Porphyrinogen Relationship: The Generation of Unprecedented Forms of Porphyrinogen ; loop_ _publ_author_name _publ_author_address 'Bonomo, Lucia' ; Institut de Chimie Min\'erale et Analytique BCH Universit\'e de Lausanne CH-1015 Lausanne Switzerland ; 'Solari, Euro' ; Institut de Chimie Min\'erale et Analytique BCH Universit\'e de Lausanne CH-1015 Lausanne Switzerland ; 'Scopelliti, Rosario' ; Institut de Chimie Min\'erale et Analytique BCH Universit\'e de Lausanne CH-1015 Lausanne Switzerland ; 'Latronico, Mario' ; Dipartimento di Ingegneria e Fisica dell'Ambiente Universit\'a della Basilicata I-85100 Potenza Italy ; 'Floriani, Carlo' ; Institut de Chimie Min\'erale et Analytique BCH Universit\'e de Lausanne CH-1015 Lausanne Switzerland ; data_3 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C32 H36 N4 Ni), 2(C12 H30 Li O6)' _chemical_formula_sum 'C56 H96 Li2 N4 Ni O12' _chemical_formula_weight 1089.96 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' 'Ni' 'Ni' 0.3393 1.1124 '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 12.269(3) _cell_length_b 19.417(4) _cell_length_c 26.192(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.49(3) _cell_angle_gamma 90.00 _cell_volume 6067(2) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used '54 spots from the first image' _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2360 _exptl_absorpt_coefficient_mu 0.379 _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 143(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'mar345 IPDS' _diffrn_measurement_method 'phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10943 _diffrn_reflns_av_R_equivalents 0.0642 _diffrn_reflns_av_sigmaI/netI 0.0771 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 24.38 _reflns_number_total 3664 _reflns_number_gt 2120 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'marresearch, mar345 1.2.11' _computing_cell_refinement 'marresearch, marHKL 1.9.1' _computing_data_reduction 'marresearch, marHKL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker, SHELXTL 5.1' _computing_publication_material 'Bruker, SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1415P)^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 SHELXL _refine_ls_extinction_coef 0.0031(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3664 _refine_ls_number_parameters 351 _refine_ls_number_restraints 34 _refine_ls_R_factor_all 0.1180 _refine_ls_R_factor_gt 0.0689 _refine_ls_wR_factor_ref 0.2153 _refine_ls_wR_factor_gt 0.1844 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.963 _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 Ni1 Ni 0.0000 0.29217(5) 0.2500 0.0580(5) Uani 1 2 d S . . N1 N -0.1579(4) 0.2913(2) 0.22707(17) 0.0632(12) Uani 1 1 d . . . C1 C -0.2330(5) 0.3182(3) 0.2529(2) 0.0683(16) Uani 1 1 d . . . C2 C -0.3410(5) 0.3030(3) 0.2250(3) 0.0828(19) Uani 1 1 d . . . H2 H -0.4089 0.3161 0.2338 0.080 Uiso 1 1 calc R . . C3 C -0.3304(6) 0.2650(4) 0.1816(3) 0.0837(19) Uani 1 1 d . . . H3 H -0.3901 0.2457 0.1558 0.080 Uiso 1 1 calc R . . C4 C -0.2190(5) 0.2601(3) 0.1824(2) 0.0687(16) Uani 1 1 d . . . C5 C -0.1639(6) 0.2234(3) 0.1451(2) 0.0777(19) Uani 1 1 d . . . N2 N 0.0117(4) 0.2919(2) 0.17955(17) 0.0628(12) Uani 1 1 d . . . C6 C -0.0646(6) 0.2639(3) 0.1377(2) 0.0727(17) Uani 1 1 d . . . C7 C -0.0285(7) 0.2761(4) 0.0932(3) 0.094(2) Uani 1 1 d . . . H7 H -0.0660 0.2626 0.0587 0.080 Uiso 1 1 calc R . . C8 C 0.0733(7) 0.3119(4) 0.1070(3) 0.094(2) Uani 1 1 d . . . H8 H 0.1181 0.3266 0.0840 0.080 Uiso 1 1 calc R . . C9 C 0.0958(6) 0.3217(3) 0.1611(2) 0.0715(17) Uani 1 1 d . . . C10 C 0.1925(6) 0.3546(4) 0.1967(3) 0.086(2) Uani 1 1 d . . . C11 C 0.2585(10) 0.3980(5) 0.1797(4) 0.161(4) Uani 1 1 d DU . . H11 H 0.2470 0.3997 0.1425 0.080 Uiso 1 1 calc R A 1 C12A C 0.3451(9) 0.4433(6) 0.2075(6) 0.172(6) Uani 0.789(12) 1 d PDU B 1 H12A H 0.3548 0.4366 0.2454 0.080 Uiso 0.789(12) 1 calc PR B 1 H12B H 0.3239 0.4911 0.1984 0.080 Uiso 0.789(12) 1 calc PR B 1 H12C H 0.4157 0.4328 0.1976 0.080 Uiso 0.789(12) 1 calc PR B 1 C12B C 0.230(4) 0.432(2) 0.1292(13) 0.136(15) Uani 0.211(12) 1 d PDU B 2 H12D H 0.2863 0.4202 0.1093 0.080 Uiso 0.211(12) 1 calc PR B 2 H12E H 0.2295 0.4819 0.1343 0.080 Uiso 0.211(12) 1 calc PR B 2 H12F H 0.1562 0.4166 0.1097 0.080 Uiso 0.211(12) 1 calc PR B 2 C13 C -0.2478(6) 0.2117(4) 0.0918(3) 0.101(2) Uani 1 1 d . . . H13A H -0.2087 0.1861 0.0686 0.080 Uiso 1 1 calc R . . H13B H -0.3089 0.1818 0.0979 0.080 Uiso 1 1 calc R . . C14 C -0.3004(6) 0.2753(4) 0.0627(3) 0.114(3) Uani 1 1 d . . . H14A H -0.3441 0.2997 0.0839 0.080 Uiso 1 1 calc R . . H14B H -0.3498 0.2617 0.0291 0.080 Uiso 1 1 calc R . . H14C H -0.2413 0.3057 0.0561 0.080 Uiso 1 1 calc R . . C15 C -0.1271(7) 0.1506(4) 0.1700(3) 0.105(3) Uani 1 1 d . . . H15A H -0.0780 0.1583 0.2053 0.080 Uiso 1 1 calc R . . H15B H -0.1951 0.1267 0.1750 0.080 Uiso 1 1 calc R . . C16 C -0.0701(8) 0.1051(5) 0.1422(4) 0.153(4) Uani 1 1 d . . . H16A H -0.1233 0.0870 0.1113 0.080 Uiso 1 1 calc R . . H16B H -0.0376 0.0669 0.1652 0.080 Uiso 1 1 calc R . . H16C H -0.0102 0.1302 0.1311 0.080 Uiso 1 1 calc R . . Li1 Li 0.3010(9) 0.0673(5) 0.1003(4) 0.080(3) Uani 1 1 d . . . C17 C 0.2318(6) 0.1344(4) 0.2000(3) 0.104(2) Uani 1 1 d . . . H17A H 0.2957 0.1216 0.2285 0.080 Uiso 1 1 calc R . . H17B H 0.1746 0.0982 0.1955 0.080 Uiso 1 1 calc R . . H17C H 0.2000 0.1780 0.2086 0.080 Uiso 1 1 calc R . . O1 O 0.2680(3) 0.1421(2) 0.15262(16) 0.0800(12) Uani 1 1 d . . . C18 C 0.3407(6) 0.1997(4) 0.1555(3) 0.088(2) Uani 1 1 d . . . H18A H 0.4148 0.1888 0.1785 0.080 Uiso 1 1 calc R . . H18B H 0.3091 0.2397 0.1705 0.080 Uiso 1 1 calc R . . C19 C 0.3530(5) 0.2163(3) 0.1021(3) 0.0805(18) Uani 1 1 d . . . H19A H 0.2811 0.2335 0.0804 0.080 Uiso 1 1 calc R . . H19B H 0.4105 0.2525 0.1038 0.080 Uiso 1 1 calc R . . O2 O 0.3854(3) 0.1560(2) 0.07964(17) 0.0840(13) Uani 1 1 d . . . C20 C 0.4050(7) 0.1691(4) 0.0295(3) 0.108(2) Uani 1 1 d . . . H20A H 0.3400 0.1927 0.0077 0.080 Uiso 1 1 calc R . . H20B H 0.4172 0.1254 0.0129 0.080 Uiso 1 1 calc R . . H20C H 0.4716 0.1982 0.0331 0.080 Uiso 1 1 calc R . . C21 C 0.0834(6) 0.1384(4) 0.0336(3) 0.104(2) Uani 1 1 d . . . H21A H 0.1070 0.1739 0.0119 0.080 Uiso 1 1 calc R . . H21B H 0.0867 0.1569 0.0687 0.080 Uiso 1 1 calc R . . H21C H 0.0065 0.1241 0.0174 0.080 Uiso 1 1 calc R . . O3 O 0.1560(4) 0.0807(3) 0.0375(2) 0.1022(15) Uani 1 1 d . . . C22 C 0.1585(8) 0.0538(5) -0.0122(4) 0.146(4) Uani 1 1 d . . . H22A H 0.1894 0.0885 -0.0327 0.080 Uiso 1 1 calc R . . H22B H 0.0818 0.0419 -0.0319 0.080 Uiso 1 1 calc R . . C23 C 0.2299(11) -0.0082(6) -0.0042(4) 0.170(4) Uani 1 1 d . . . H23A H 0.1932 -0.0448 0.0122 0.080 Uiso 1 1 calc R . . H23B H 0.2387 -0.0254 -0.0386 0.080 Uiso 1 1 calc R . . O4 O 0.3320(5) 0.0057(3) 0.0270(3) 0.1186(17) Uani 1 1 d . . . C24 C 0.4069(8) -0.0499(5) 0.0300(4) 0.154(4) Uani 1 1 d . . . H24A H 0.3778 -0.0898 0.0456 0.080 Uiso 1 1 calc R . . H24B H 0.4802 -0.0369 0.0519 0.080 Uiso 1 1 calc R . . H24C H 0.4149 -0.0618 -0.0053 0.080 Uiso 1 1 calc R . . C25 C 0.1197(7) -0.0383(5) 0.1202(4) 0.141(3) Uani 1 1 d . . . H25A H 0.1131 -0.0761 0.1441 0.080 Uiso 1 1 calc R . . H25B H 0.0965 -0.0543 0.0838 0.080 Uiso 1 1 calc R . . H25C H 0.0716 0.0000 0.1256 0.080 Uiso 1 1 calc R . . O5 O 0.2296(4) -0.0163(2) 0.13023(19) 0.0958(14) Uani 1 1 d . . . C26 C 0.3067(8) -0.0563(5) 0.1621(4) 0.133(3) Uani 1 1 d . . . H26A H 0.2824 -0.0630 0.1953 0.080 Uiso 1 1 calc R . . H26B H 0.3059 -0.1020 0.1453 0.080 Uiso 1 1 calc R . . C27 C 0.4135(9) -0.0335(5) 0.1745(4) 0.142(3) Uani 1 1 d . . . H27A H 0.4620 -0.0716 0.1678 0.080 Uiso 1 1 calc R . . H27B H 0.4339 -0.0244 0.2127 0.080 Uiso 1 1 calc R . . O6 O 0.4410(4) 0.0248(3) 0.1493(2) 0.1050(15) Uani 1 1 d . . . C28 C 0.5478(8) 0.0497(5) 0.1593(5) 0.198(6) Uani 1 1 d . . . H28A H 0.5599 0.0810 0.1895 0.080 Uiso 1 1 calc R . . H28B H 0.5593 0.0748 0.1285 0.080 Uiso 1 1 calc R . . H28C H 0.6010 0.0114 0.1671 0.080 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 Ni1 0.0683(8) 0.0584(7) 0.0458(7) 0.000 0.0104(5) 0.000 N1 0.073(3) 0.067(3) 0.047(3) 0.004(2) 0.009(3) 0.000(3) C1 0.069(4) 0.073(4) 0.067(4) 0.008(3) 0.024(3) 0.002(3) C2 0.064(4) 0.099(5) 0.084(5) 0.016(4) 0.016(4) 0.014(4) C3 0.074(5) 0.102(5) 0.066(5) -0.002(4) -0.002(3) -0.002(4) C4 0.067(4) 0.070(4) 0.062(4) 0.008(3) 0.000(3) 0.002(3) C5 0.086(4) 0.082(5) 0.053(4) -0.010(3) -0.008(3) 0.015(4) N2 0.071(3) 0.069(3) 0.047(3) 0.005(2) 0.012(3) 0.012(3) C6 0.089(5) 0.089(4) 0.039(4) 0.000(3) 0.014(4) 0.029(4) C7 0.098(5) 0.126(6) 0.052(5) -0.004(4) 0.004(4) 0.037(5) C8 0.113(6) 0.119(6) 0.059(5) 0.025(4) 0.039(4) 0.045(5) C9 0.087(5) 0.077(4) 0.055(4) 0.009(3) 0.025(4) 0.026(4) C10 0.086(5) 0.100(5) 0.082(5) 0.034(4) 0.042(4) 0.004(4) C11 0.213(11) 0.141(9) 0.120(8) 0.036(6) 0.023(8) -0.028(7) C12A 0.108(9) 0.153(11) 0.248(16) 0.098(10) 0.027(8) -0.017(7) C12B 0.17(3) 0.12(3) 0.13(2) 0.03(2) 0.07(3) 0.04(3) C13 0.108(5) 0.121(6) 0.058(4) -0.019(4) -0.009(4) 0.013(5) C14 0.104(6) 0.163(8) 0.057(5) -0.007(5) -0.015(4) 0.020(5) C15 0.126(6) 0.105(6) 0.071(5) -0.024(4) -0.002(4) 0.037(5) C16 0.176(9) 0.128(8) 0.148(9) 0.002(7) 0.022(7) -0.005(7) Li1 0.083(7) 0.084(7) 0.073(7) 0.009(6) 0.014(5) 0.006(5) C17 0.116(6) 0.110(6) 0.096(6) -0.004(5) 0.044(5) -0.002(5) O1 0.092(3) 0.082(3) 0.069(3) -0.003(2) 0.024(2) -0.003(2) C18 0.088(5) 0.100(5) 0.075(5) -0.016(4) 0.018(4) -0.003(4) C19 0.083(4) 0.071(5) 0.091(5) -0.007(4) 0.026(4) 0.002(3) O2 0.104(3) 0.080(3) 0.072(3) 0.008(2) 0.030(2) 0.014(2) C20 0.146(7) 0.100(5) 0.091(6) 0.018(4) 0.054(5) 0.005(5) C21 0.091(5) 0.102(6) 0.110(6) 0.014(4) 0.006(4) 0.017(5) O3 0.105(3) 0.098(4) 0.090(4) -0.008(3) -0.003(3) 0.023(3) C22 0.160(9) 0.159(9) 0.093(7) -0.034(6) -0.024(6) 0.035(7) C23 0.175(11) 0.181(12) 0.143(10) -0.074(9) 0.014(8) 0.005(9) O4 0.125(4) 0.094(4) 0.141(5) -0.004(3) 0.041(4) 0.029(3) C24 0.193(10) 0.119(7) 0.178(10) 0.002(7) 0.099(8) 0.036(7) C25 0.114(7) 0.106(7) 0.191(10) 0.015(6) 0.007(6) -0.020(5) O5 0.094(3) 0.086(3) 0.103(4) 0.022(3) 0.014(3) -0.003(3) C26 0.108(7) 0.131(8) 0.145(8) 0.060(6) -0.001(6) -0.007(6) C27 0.139(9) 0.104(7) 0.167(9) 0.060(6) 0.005(7) 0.035(6) O6 0.087(3) 0.088(4) 0.128(4) 0.023(3) 0.000(3) 0.003(3) C28 0.113(8) 0.151(9) 0.293(16) 0.098(10) -0.026(8) 0.000(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 Ni1 N2 1.884(4) . ? Ni1 N2 1.884(4) 2 ? Ni1 N1 1.889(4) . ? Ni1 N1 1.889(5) 2 ? Ni1 H15A 2.9193 . ? Ni1 H15A 2.9193 2 ? N1 C1 1.369(7) . ? N1 C4 1.373(7) . ? C1 C2 1.388(8) . ? C1 C10 1.477(9) 2 ? C2 C3 1.388(9) . ? C3 C4 1.364(8) . ? C4 C5 1.494(8) . ? C5 C6 1.500(9) . ? C5 C13 1.546(8) . ? C5 C15 1.577(9) . ? N2 C9 1.366(8) . ? N2 C6 1.377(7) . ? C6 C7 1.360(9) . ? C7 C8 1.402(10) . ? C8 C9 1.392(8) . ? C9 C10 1.473(9) . ? C10 C11 1.316(11) . ? C10 C1 1.477(9) 2 ? C11 C12A 1.439(14) . ? C11 C12B 1.45(2) . ? C13 C14 1.515(9) . ? C15 C16 1.428(10) . ? Li1 O6 2.062(11) . ? Li1 O5 2.083(11) . ? Li1 O1 2.101(11) . ? Li1 O3 2.138(11) . ? Li1 O2 2.143(11) . ? Li1 O4 2.367(12) . ? C17 O1 1.420(7) . ? O1 C18 1.420(7) . ? C18 C19 1.476(8) . ? C19 O2 1.407(7) . ? O2 C20 1.412(7) . ? C21 O3 1.419(7) . ? O3 C22 1.410(9) . ? C22 C23 1.475(12) . ? C23 O4 1.354(11) . ? O4 C24 1.408(8) . ? C25 O5 1.379(8) . ? O5 C26 1.351(8) . ? C26 C27 1.349(10) . ? C27 O6 1.391(9) . ? O6 C28 1.363(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ni1 N2 179.7(3) . 2 ? N2 Ni1 N1 89.71(19) . . ? N2 Ni1 N1 90.28(19) 2 . ? N2 Ni1 N1 90.28(19) . 2 ? N2 Ni1 N1 89.71(19) 2 2 ? N1 Ni1 N1 178.9(3) . 2 ? N2 Ni1 H15A 72.4 . . ? N2 Ni1 H15A 107.3 2 . ? N1 Ni1 H15A 69.4 . . ? N1 Ni1 H15A 109.6 2 . ? N2 Ni1 H15A 107.3 . 2 ? N2 Ni1 H15A 72.4 2 2 ? N1 Ni1 H15A 109.6 . 2 ? N1 Ni1 H15A 69.4 2 2 ? H15A Ni1 H15A 54.1 . 2 ? C1 N1 C4 107.0(5) . . ? C1 N1 Ni1 126.7(4) . . ? C4 N1 Ni1 126.2(4) . . ? N1 C1 C2 109.1(6) . . ? N1 C1 C10 120.0(6) . 2 ? C2 C1 C10 130.8(6) . 2 ? C3 C2 C1 106.5(6) . . ? C4 C3 C2 108.0(6) . . ? C3 C4 N1 109.3(6) . . ? C3 C4 C5 128.8(6) . . ? N1 C4 C5 121.8(5) . . ? C4 C5 C6 109.8(5) . . ? C4 C5 C13 110.7(6) . . ? C6 C5 C13 110.5(6) . . ? C4 C5 C15 106.6(5) . . ? C6 C5 C15 111.2(5) . . ? C13 C5 C15 108.0(5) . . ? C9 N2 C6 108.3(5) . . ? C9 N2 Ni1 125.6(4) . . ? C6 N2 Ni1 126.1(4) . . ? C7 C6 N2 108.5(6) . . ? C7 C6 C5 129.7(7) . . ? N2 C6 C5 121.7(5) . . ? C6 C7 C8 108.3(6) . . ? C9 C8 C7 106.4(6) . . ? N2 C9 C8 108.4(6) . . ? N2 C9 C10 121.6(6) . . ? C8 C9 C10 130.0(7) . . ? C11 C10 C9 122.2(8) . . ? C11 C10 C1 120.2(8) . 2 ? C9 C10 C1 114.3(6) . 2 ? C10 C11 C12A 131.2(11) . . ? C10 C11 C12B 125(2) . . ? C12A C11 C12B 100(2) . . ? C14 C13 C5 116.8(6) . . ? C16 C15 C5 118.1(7) . . ? O6 Li1 O5 79.4(4) . . ? O6 Li1 O1 97.4(5) . . ? O5 Li1 O1 97.5(5) . . ? O6 Li1 O3 161.9(6) . . ? O5 Li1 O3 92.1(5) . . ? O1 Li1 O3 99.5(4) . . ? O6 Li1 O2 95.6(5) . . ? O5 Li1 O2 172.6(6) . . ? O1 Li1 O2 77.7(4) . . ? O3 Li1 O2 94.2(4) . . ? O6 Li1 O4 92.0(4) . . ? O5 Li1 O4 94.2(5) . . ? O1 Li1 O4 166.1(6) . . ? O3 Li1 O4 72.6(4) . . ? O2 Li1 O4 91.4(4) . . ? C17 O1 C18 111.0(5) . . ? C17 O1 Li1 130.1(5) . . ? C18 O1 Li1 111.4(5) . . ? O1 C18 C19 108.9(5) . . ? O2 C19 C18 108.4(5) . . ? C19 O2 C20 111.4(5) . . ? C19 O2 Li1 111.3(5) . . ? C20 O2 Li1 125.2(5) . . ? C22 O3 C21 111.9(6) . . ? C22 O3 Li1 118.1(5) . . ? C21 O3 Li1 123.2(5) . . ? O3 C22 C23 108.1(8) . . ? O4 C23 C22 111.0(9) . . ? C23 O4 C24 112.4(8) . . ? C23 O4 Li1 106.8(6) . . ? C24 O4 Li1 124.6(6) . . ? C26 O5 C25 116.9(6) . . ? C26 O5 Li1 112.6(6) . . ? C25 O5 Li1 130.3(6) . . ? C27 C26 O5 117.5(7) . . ? C26 C27 O6 118.8(7) . . ? C28 O6 C27 121.7(7) . . ? C28 O6 Li1 127.0(6) . . ? C27 O6 Li1 111.2(6) . . ? _refine_diff_density_max 0.384 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.079 data_7 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C46 H73 Li4 N5 O6' _chemical_formula_sum 'C46 H73 Li4 N5 O6' _chemical_formula_weight 819.85 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' _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 11.755(2) _cell_length_b 20.644(4) _cell_length_c 19.117(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.22(3) _cell_angle_gamma 90.00 _cell_volume 4619.9(16) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used '118 spots from the first image' _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description irregular _exptl_crystal_colour orange _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.179 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1776 _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 143(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'mar345 IPDS' _diffrn_measurement_method 'phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24492 _diffrn_reflns_av_R_equivalents 0.0531 _diffrn_reflns_av_sigmaI/netI 0.0507 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 24.40 _reflns_number_total 7078 _reflns_number_gt 4735 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'marresearch, mar345 1.2.11' _computing_cell_refinement 'marresearch, marHKL 1.9.1' _computing_data_reduction 'marresearch, marHKL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker, SHELXTL 5.1' _computing_publication_material 'Bruker, SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1770P)^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 SHELXL _refine_ls_extinction_coef 0.046(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 7078 _refine_ls_number_parameters 561 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1051 _refine_ls_R_factor_gt 0.0789 _refine_ls_wR_factor_ref 0.2481 _refine_ls_wR_factor_gt 0.2282 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 -0.1442(4) 0.2319(3) 0.0362(3) 0.0432(13) Uani 1 1 d . . . N1 N -0.2596(2) 0.24232(12) 0.10966(13) 0.0364(6) Uani 1 1 d . . . C1 C -0.3251(3) 0.19092(15) 0.13015(16) 0.0387(8) Uani 1 1 d . . . C2 C -0.4324(3) 0.21247(17) 0.14333(18) 0.0448(8) Uani 1 1 d . . . H2 H -0.4927 0.1867 0.1582 0.054 Uiso 1 1 calc R . . C3 C -0.4356(3) 0.27986(16) 0.13059(18) 0.0421(8) Uani 1 1 d . . . H3 H -0.4981 0.3083 0.1351 0.050 Uiso 1 1 calc R . . C4 C -0.3289(3) 0.29603(15) 0.11003(16) 0.0373(7) Uani 1 1 d . . . C5 C -0.2855(3) 0.36183(15) 0.08606(17) 0.0375(8) Uani 1 1 d . . . N2 N -0.0867(2) 0.33196(12) 0.05928(13) 0.0376(6) Uani 1 1 d . . . C6 C -0.1571(3) 0.36283(14) 0.10268(16) 0.0364(7) Uani 1 1 d . . . C7 C -0.0940(3) 0.38210(15) 0.16395(17) 0.0400(8) Uani 1 1 d . . . H7 H -0.1221 0.4045 0.2022 0.048 Uiso 1 1 calc R . . C8 C 0.0197(3) 0.36227(15) 0.15877(17) 0.0406(8) Uani 1 1 d . . . H8 H 0.0826 0.3684 0.1930 0.049 Uiso 1 1 calc R . . C9 C 0.0223(2) 0.33197(15) 0.09378(16) 0.0374(7) Uani 1 1 d . . . C10 C 0.1224(2) 0.31232(15) 0.05364(16) 0.0373(8) Uani 1 1 d . . . N3 N 0.0076(2) 0.22883(12) -0.01714(14) 0.0382(6) Uani 1 1 d . . . C11 C 0.1093(3) 0.24598(15) 0.02034(17) 0.0378(7) Uani 1 1 d . . . C12 C 0.1919(3) 0.19885(16) 0.01186(18) 0.0422(8) Uani 1 1 d . . . H12 H 0.2694 0.1996 0.0310 0.051 Uiso 1 1 calc R . . C13 C 0.1385(3) 0.15030(16) -0.03032(18) 0.0434(8) Uani 1 1 d . . . H13 H 0.1727 0.1114 -0.0448 0.052 Uiso 1 1 calc R . . C14 C 0.0264(3) 0.16946(15) -0.04707(17) 0.0394(8) Uani 1 1 d . . . C15 C -0.0729(3) 0.13154(16) -0.08358(17) 0.0407(8) Uani 1 1 d . . . N4 N -0.1861(2) 0.13943(13) 0.02137(13) 0.0390(7) Uani 1 1 d . . . C16 C -0.1346(2) 0.10029(15) -0.02498(16) 0.0387(8) Uani 1 1 d . . . C17 C -0.1405(3) 0.03556(16) -0.00516(18) 0.0439(8) Uani 1 1 d . . . H17 H -0.1118 -0.0007 -0.0285 0.053 Uiso 1 1 calc R . . C18 C -0.1977(3) 0.03472(16) 0.05677(17) 0.0427(8) Uani 1 1 d . . . H18 H -0.2160 -0.0025 0.0827 0.051 Uiso 1 1 calc R . . C19 C -0.2225(3) 0.09908(16) 0.07273(17) 0.0390(8) Uani 1 1 d . . . C20 C -0.2803(3) 0.12391(15) 0.13286(16) 0.0390(8) Uani 1 1 d . B . C21 C -0.3147(3) 0.36945(17) 0.00611(18) 0.0457(8) Uani 1 1 d . . . H21A H -0.2761 0.4088 -0.0094 0.055 Uiso 1 1 calc R . . H21B H -0.2824 0.3320 -0.0176 0.055 Uiso 1 1 calc R . . C22 C -0.4414(3) 0.37434(19) -0.0186(2) 0.0562(10) Uani 1 1 d . . . H22A H -0.4815 0.3363 -0.0024 0.084 Uiso 1 1 calc R . . H22B H -0.4510 0.3762 -0.0700 0.084 Uiso 1 1 calc R . . H22C H -0.4732 0.4137 0.0008 0.084 Uiso 1 1 calc R . . C23 C -0.3419(3) 0.41609(16) 0.1261(2) 0.0463(9) Uani 1 1 d . . . H23A H -0.4257 0.4101 0.1196 0.056 Uiso 1 1 calc R . . H23B H -0.3180 0.4112 0.1768 0.056 Uiso 1 1 calc R . . C24 C -0.3144(3) 0.48454(17) 0.1042(2) 0.0609(11) Uani 1 1 d . . . H24A H -0.2317 0.4916 0.1112 0.091 Uiso 1 1 calc R . . H24B H -0.3532 0.5155 0.1327 0.091 Uiso 1 1 calc R . . H24C H -0.3406 0.4908 0.0545 0.091 Uiso 1 1 calc R . . C25 C 0.2360(3) 0.31776(17) 0.10060(18) 0.0446(8) Uani 1 1 d . . . H25A H 0.2997 0.3117 0.0707 0.054 Uiso 1 1 calc R . . H25B H 0.2422 0.3622 0.1200 0.054 Uiso 1 1 calc R . . C26 C 0.2514(3) 0.26956(18) 0.16202(18) 0.0495(9) Uani 1 1 d . . . H26A H 0.1825 0.2694 0.1873 0.074 Uiso 1 1 calc R . . H26B H 0.3173 0.2825 0.1941 0.074 Uiso 1 1 calc R . . H26C H 0.2643 0.2261 0.1438 0.074 Uiso 1 1 calc R . . N5 N 0.1170(2) 0.36068(13) -0.00812(14) 0.0418(7) Uani 1 1 d . . . C27 C 0.1234(3) 0.42847(16) 0.01399(19) 0.0510(9) Uani 1 1 d . . . H27A H 0.1991 0.4372 0.0380 0.077 Uiso 1 1 calc R . . H27B H 0.0647 0.4371 0.0461 0.077 Uiso 1 1 calc R . . H27C H 0.1107 0.4566 -0.0273 0.077 Uiso 1 1 calc R . . C28 C 0.2040(3) 0.34898(18) -0.05765(19) 0.0524(9) Uani 1 1 d . . . H28A H 0.1894 0.3773 -0.0986 0.079 Uiso 1 1 calc R . . H28B H 0.2004 0.3036 -0.0729 0.079 Uiso 1 1 calc R . . H28C H 0.2800 0.3582 -0.0343 0.079 Uiso 1 1 calc R . . C29 C -0.0298(3) 0.07761(18) -0.12978(18) 0.0494(9) Uani 1 1 d . . . H29A H 0.0240 0.0499 -0.1002 0.059 Uiso 1 1 calc R . . H29B H -0.0956 0.0503 -0.1471 0.059 Uiso 1 1 calc R . . C30 C 0.0291(4) 0.1005(2) -0.1919(2) 0.0707(13) Uani 1 1 d . . . H30A H -0.0249 0.1252 -0.2236 0.106 Uiso 1 1 calc R . . H30B H 0.0565 0.0630 -0.2169 0.106 Uiso 1 1 calc R . . H30C H 0.0940 0.1281 -0.1756 0.106 Uiso 1 1 calc R . . C31 C -0.1539(3) 0.17716(17) -0.12814(18) 0.0475(9) Uani 1 1 d . . . H31A H -0.1857 0.2089 -0.0964 0.057 Uiso 1 1 calc R . . H31B H -0.1085 0.2016 -0.1604 0.057 Uiso 1 1 calc R . . C32 C -0.2530(3) 0.1445(2) -0.1715(2) 0.0614(10) Uani 1 1 d . . . H32A H -0.2243 0.1224 -0.2117 0.092 Uiso 1 1 calc R . . H32B H -0.3092 0.1773 -0.1884 0.092 Uiso 1 1 calc R . . H32C H -0.2891 0.1130 -0.1423 0.092 Uiso 1 1 calc R . . C33 C -0.2963(3) 0.08469(18) 0.18744(18) 0.0488(9) Uani 1 1 d . . . H33 H -0.2602 0.0436 0.1858 0.059 Uiso 1 1 calc R A 1 C34A C -0.3596(4) 0.0947(3) 0.2483(3) 0.0553(16) Uani 0.747(8) 1 d P B 1 H34A H -0.3720 0.1412 0.2548 0.083 Uiso 0.747(8) 1 calc PR B 1 H34B H -0.3160 0.0771 0.2902 0.083 Uiso 0.747(8) 1 calc PR B 1 H34C H -0.4335 0.0726 0.2412 0.083 Uiso 0.747(8) 1 calc PR B 1 C34B C -0.2396(14) 0.0242(7) 0.2143(8) 0.057(5) Uani 0.253(8) 1 d P B 2 H34D H -0.2721 -0.0128 0.1874 0.086 Uiso 0.253(8) 1 calc PR B 2 H34E H -0.2519 0.0187 0.2640 0.086 Uiso 0.253(8) 1 calc PR B 2 H34F H -0.1575 0.0269 0.2093 0.086 Uiso 0.253(8) 1 calc PR B 2 Li2 Li -0.3212(5) 0.0781(3) -0.0290(3) 0.0494(14) Uani 1 1 d . . . C35 C -0.4721(3) 0.19617(19) -0.0442(2) 0.0610(10) Uani 1 1 d . . . H35A H -0.4486 0.2150 -0.0877 0.092 Uiso 1 1 calc R . . H35B H -0.4223 0.2124 -0.0041 0.092 Uiso 1 1 calc R . . H35C H -0.5513 0.2084 -0.0386 0.092 Uiso 1 1 calc R . . O1 O -0.4632(2) 0.12639(13) -0.04736(14) 0.0591(7) Uani 1 1 d . . . C36 C -0.5326(3) 0.0993(2) -0.1050(3) 0.0752(13) Uani 1 1 d . . . H36A H -0.5072 0.1150 -0.1500 0.090 Uiso 1 1 calc R . . H36B H -0.6134 0.1119 -0.1028 0.090 Uiso 1 1 calc R . . C37 C -0.5197(4) 0.0271(3) -0.0997(3) 0.0859(15) Uani 1 1 d . . . H37A H -0.5585 0.0106 -0.0594 0.103 Uiso 1 1 calc R . . H37B H -0.5547 0.0062 -0.1431 0.103 Uiso 1 1 calc R . . O2 O -0.4013(2) 0.01267(13) -0.09016(14) 0.0632(7) Uani 1 1 d . . . C38 C -0.3781(4) -0.0546(2) -0.0927(3) 0.0781(13) Uani 1 1 d . . . H38A H -0.4311 -0.0782 -0.0652 0.117 Uiso 1 1 calc R . . H38B H -0.2995 -0.0628 -0.0732 0.117 Uiso 1 1 calc R . . H38C H -0.3878 -0.0695 -0.1416 0.117 Uiso 1 1 calc R . . Li3 Li -0.1061(5) 0.2664(3) 0.1699(3) 0.0480(14) Uani 1 1 d . . . C39 C -0.2317(3) 0.2863(2) 0.29222(19) 0.0546(10) Uani 1 1 d . . . H39A H -0.2941 0.2628 0.2658 0.082 Uiso 1 1 calc R . . H39B H -0.2374 0.3325 0.2807 0.082 Uiso 1 1 calc R . . H39C H -0.2372 0.2803 0.3427 0.082 Uiso 1 1 calc R . . O3 O -0.12456(19) 0.26176(11) 0.27399(12) 0.0491(6) Uani 1 1 d . . . C40 C -0.1070(3) 0.19634(18) 0.2950(2) 0.0549(9) Uani 1 1 d . . . H40A H -0.1746 0.1700 0.2785 0.066 Uiso 1 1 calc R . . H40B H -0.0959 0.1936 0.3468 0.066 Uiso 1 1 calc R . . C41 C -0.0046(3) 0.1713(2) 0.26416(19) 0.0602(11) Uani 1 1 d . . . H41A H 0.0647 0.1936 0.2855 0.072 Uiso 1 1 calc R . . H41B H 0.0039 0.1243 0.2735 0.072 Uiso 1 1 calc R . . O4 O -0.0178(2) 0.18281(12) 0.19019(12) 0.0527(7) Uani 1 1 d . . . C42 C 0.0386(3) 0.13596(17) 0.15080(19) 0.0509(9) Uani 1 1 d . . . H42A H 0.1212 0.1382 0.1637 0.076 Uiso 1 1 calc R . . H42B H 0.0227 0.1449 0.1005 0.076 Uiso 1 1 calc R . . H42C H 0.0108 0.0926 0.1612 0.076 Uiso 1 1 calc R . . Li4 Li -0.0460(5) 0.3221(3) -0.0426(3) 0.0450(13) Uani 1 1 d . . . C43 C -0.1407(8) 0.3426(3) -0.1933(3) 0.178(4) Uani 1 1 d . . . H43A H -0.1986 0.3710 -0.2173 0.080 Uiso 1 1 calc R . . H43B H -0.1720 0.2989 -0.1900 0.080 Uiso 1 1 calc R . . H43C H -0.0733 0.3413 -0.2198 0.080 Uiso 1 1 calc R . . O5 O -0.1108(2) 0.36577(12) -0.12771(13) 0.0589(7) Uani 1 1 d . . . C44 C -0.0975(4) 0.4343(2) -0.1246(2) 0.0700(12) Uani 1 1 d . . . H44A H -0.0210 0.4459 -0.1385 0.084 Uiso 1 1 calc R . . H44B H -0.1018 0.4489 -0.0755 0.084 Uiso 1 1 calc R . . C45 C -0.1855(4) 0.4687(3) -0.1708(3) 0.0808(13) Uani 1 1 d . . . H45A H -0.1677 0.5155 -0.1710 0.097 Uiso 1 1 calc R . . H45B H -0.1851 0.4523 -0.2194 0.097 Uiso 1 1 calc R . . O6 O -0.2959(4) 0.4592(3) -0.1470(3) 0.1357(16) Uani 1 1 d . . . C46 C -0.3824(6) 0.5010(4) -0.1798(5) 0.156(3) Uani 1 1 d . . . H46A H -0.3615 0.5462 -0.1699 0.080 Uiso 1 1 calc R . . H46B H -0.4556 0.4915 -0.1613 0.080 Uiso 1 1 calc R . . H46C H -0.3892 0.4937 -0.2307 0.080 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 0.046(3) 0.044(3) 0.039(3) 0.002(2) 0.005(2) 0.001(2) N1 0.0360(13) 0.0359(15) 0.0376(15) 0.0022(11) 0.0048(12) 0.0002(11) C1 0.0395(17) 0.0380(19) 0.0388(18) 0.0002(14) 0.0043(14) -0.0045(13) C2 0.0372(17) 0.050(2) 0.048(2) 0.0001(16) 0.0074(15) -0.0048(14) C3 0.0349(16) 0.042(2) 0.050(2) -0.0014(15) 0.0074(15) -0.0012(13) C4 0.0378(16) 0.0372(18) 0.0374(17) -0.0015(14) 0.0056(14) -0.0016(13) C5 0.0362(16) 0.0353(18) 0.0416(18) 0.0021(14) 0.0061(14) 0.0021(13) N2 0.0355(14) 0.0375(16) 0.0403(15) 0.0002(12) 0.0051(12) -0.0009(11) C6 0.0395(16) 0.0328(18) 0.0381(18) 0.0004(13) 0.0092(14) -0.0002(13) C7 0.0431(17) 0.0387(19) 0.0392(18) -0.0044(14) 0.0088(14) -0.0017(14) C8 0.0396(17) 0.043(2) 0.0388(18) -0.0038(14) 0.0026(14) -0.0024(13) C9 0.0342(16) 0.0405(19) 0.0378(18) 0.0009(14) 0.0046(14) -0.0022(13) C10 0.0335(16) 0.0401(19) 0.0390(18) 0.0019(14) 0.0076(14) -0.0028(13) N3 0.0367(13) 0.0378(16) 0.0406(15) -0.0017(12) 0.0061(12) -0.0028(11) C11 0.0363(16) 0.0386(19) 0.0393(18) -0.0016(14) 0.0079(14) -0.0030(13) C12 0.0328(16) 0.046(2) 0.049(2) 0.0013(16) 0.0089(14) 0.0011(13) C13 0.0438(18) 0.0386(19) 0.049(2) -0.0053(15) 0.0107(16) 0.0032(14) C14 0.0420(17) 0.0382(19) 0.0391(18) -0.0034(14) 0.0101(15) 0.0011(13) C15 0.0428(18) 0.0404(19) 0.0392(18) -0.0037(14) 0.0061(15) -0.0034(13) N4 0.0373(14) 0.0398(16) 0.0398(15) -0.0006(12) 0.0021(12) -0.0008(11) C16 0.0360(16) 0.0406(19) 0.0397(18) -0.0049(14) 0.0048(14) -0.0026(13) C17 0.0422(18) 0.0373(19) 0.052(2) -0.0050(15) 0.0023(16) 0.0011(14) C18 0.0440(17) 0.0357(19) 0.049(2) 0.0029(15) 0.0045(15) 0.0003(13) C19 0.0392(16) 0.0387(19) 0.0390(18) 0.0002(14) 0.0039(14) -0.0039(13) C20 0.0391(17) 0.0392(19) 0.0379(18) 0.0003(14) 0.0003(14) -0.0054(13) C21 0.0421(18) 0.049(2) 0.046(2) 0.0077(16) 0.0033(15) 0.0009(14) C22 0.0464(19) 0.064(3) 0.057(2) 0.0081(19) -0.0063(17) 0.0036(17) C23 0.0412(17) 0.0378(19) 0.062(2) -0.0029(16) 0.0165(16) 0.0000(14) C24 0.056(2) 0.037(2) 0.092(3) -0.004(2) 0.018(2) 0.0020(16) C25 0.0366(17) 0.051(2) 0.047(2) -0.0064(16) 0.0042(15) -0.0052(14) C26 0.0427(18) 0.057(2) 0.048(2) -0.0031(17) -0.0006(16) 0.0005(15) N5 0.0492(16) 0.0367(16) 0.0415(16) 0.0021(12) 0.0149(13) 0.0002(11) C27 0.063(2) 0.040(2) 0.052(2) -0.0015(16) 0.0121(17) -0.0040(16) C28 0.056(2) 0.052(2) 0.053(2) 0.0035(17) 0.0237(18) -0.0014(16) C29 0.052(2) 0.052(2) 0.046(2) -0.0125(16) 0.0086(17) -0.0056(16) C30 0.073(3) 0.080(3) 0.064(3) -0.021(2) 0.029(2) -0.021(2) C31 0.053(2) 0.050(2) 0.0395(19) 0.0011(15) 0.0042(16) -0.0014(15) C32 0.063(2) 0.072(3) 0.048(2) 0.0038(19) -0.0027(18) -0.0075(19) C33 0.0499(19) 0.050(2) 0.047(2) 0.0058(16) 0.0035(16) -0.0031(16) C34A 0.060(3) 0.060(3) 0.046(3) 0.001(2) 0.005(2) -0.007(2) C34B 0.085(11) 0.040(9) 0.047(9) 0.020(7) 0.007(7) -0.001(7) Li2 0.044(3) 0.055(4) 0.049(3) -0.001(3) 0.003(3) -0.004(3) C35 0.058(2) 0.058(3) 0.066(3) 0.003(2) 0.002(2) 0.0095(18) O1 0.0494(14) 0.0641(18) 0.0615(17) -0.0022(13) -0.0069(12) -0.0029(12) C36 0.053(2) 0.090(4) 0.079(3) -0.011(3) -0.016(2) -0.006(2) C37 0.058(3) 0.090(4) 0.106(4) -0.020(3) -0.016(3) -0.016(2) O2 0.0590(15) 0.0574(18) 0.0707(18) -0.0071(14) -0.0076(13) -0.0115(12) C38 0.091(3) 0.054(3) 0.089(3) -0.019(2) 0.006(3) -0.013(2) Li3 0.052(3) 0.044(3) 0.049(3) 0.003(3) 0.010(3) 0.001(2) C39 0.049(2) 0.067(3) 0.049(2) -0.0017(18) 0.0123(17) 0.0062(17) O3 0.0492(13) 0.0529(16) 0.0458(14) 0.0033(11) 0.0071(11) 0.0043(11) C40 0.063(2) 0.053(2) 0.049(2) 0.0097(18) 0.0096(18) 0.0048(17) C41 0.070(3) 0.066(3) 0.044(2) 0.0142(19) 0.0026(18) 0.0142(19) O4 0.0571(15) 0.0564(16) 0.0451(14) 0.0066(11) 0.0075(11) 0.0119(11) C42 0.0466(19) 0.050(2) 0.057(2) -0.0002(17) 0.0101(17) 0.0079(15) Li4 0.050(3) 0.044(3) 0.042(3) -0.002(2) 0.008(3) 0.004(2) C43 0.325(12) 0.104(5) 0.089(5) 0.046(4) -0.074(6) -0.078(6) O5 0.0801(18) 0.0498(16) 0.0464(15) 0.0046(12) 0.0028(13) 0.0082(13) C44 0.081(3) 0.057(3) 0.072(3) 0.005(2) 0.006(2) 0.009(2) C45 0.081(3) 0.076(3) 0.084(3) 0.006(3) 0.000(3) 0.011(2) O6 0.118(3) 0.146(4) 0.144(4) 0.039(3) 0.015(3) 0.012(3) C46 0.139(6) 0.131(6) 0.192(8) 0.029(6) -0.013(6) 0.043(5) _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 N4 1.984(6) . ? Li1 N1 2.050(6) . ? Li1 N3 2.136(6) . ? Li1 N2 2.206(6) . ? Li1 Li3 2.653(8) . ? Li1 Li4 2.718(7) . ? N1 C4 1.376(4) . ? N1 C1 1.388(4) . ? N1 Li3 2.110(7) . ? C1 C2 1.382(4) . ? C1 C20 1.480(4) . ? C2 C3 1.412(5) . ? C3 C4 1.389(4) . ? C4 C5 1.536(4) . ? C5 C6 1.514(4) . ? C5 C23 1.540(4) . ? C5 C21 1.544(5) . ? N2 C6 1.380(4) . ? N2 C9 1.387(4) . ? N2 Li4 2.057(6) . ? N2 Li3 2.538(6) . ? C6 C7 1.386(5) . ? C6 Li3 2.415(6) . ? C7 C8 1.410(4) . ? C7 Li3 2.395(7) . ? C8 C9 1.394(4) . ? C8 Li3 2.490(6) . ? C9 C10 1.517(4) . ? C9 Li3 2.574(6) . ? C9 Li4 2.664(7) . ? C10 C11 1.512(4) . ? C10 N5 1.543(4) . ? C10 C25 1.544(4) . ? C10 Li4 2.584(7) . ? N3 C14 1.379(4) . ? N3 C11 1.382(4) . ? N3 Li4 2.070(6) . ? C11 C12 1.395(4) . ? C11 Li4 2.616(6) . ? C12 C13 1.399(5) . ? C13 C14 1.385(4) . ? C14 C15 1.521(4) . ? C15 C16 1.532(4) . ? C15 C29 1.536(4) . ? C15 C31 1.541(5) . ? N4 C16 1.379(4) . ? N4 C19 1.385(4) . ? N4 Li2 2.185(6) . ? C16 C17 1.393(5) . ? C16 Li2 2.234(6) . ? C17 C18 1.414(5) . ? C17 Li2 2.306(7) . ? C18 C19 1.400(5) . ? C18 Li2 2.273(7) . ? C19 C20 1.479(4) . ? C19 Li2 2.215(7) . ? C20 C33 1.347(5) . ? C21 C22 1.524(4) . ? C23 C24 1.517(5) . ? C25 C26 1.537(5) . ? N5 C27 1.462(4) . ? N5 C28 1.476(4) . ? N5 Li4 2.123(6) . ? C29 C30 1.503(5) . ? C31 C32 1.523(5) . ? C33 C34A 1.452(6) . ? C33 C34B 1.484(14) . ? Li2 O1 1.948(6) . ? Li2 O2 1.970(6) . ? C35 O1 1.446(5) . ? O1 C36 1.425(5) . ? C36 C37 1.501(6) . ? C37 O2 1.419(5) . ? O2 C38 1.418(5) . ? Li3 O3 2.024(6) . ? Li3 O4 2.034(6) . ? C39 O3 1.430(4) . ? O3 C40 1.419(4) . ? C40 C41 1.480(5) . ? C41 O4 1.428(4) . ? O4 C42 1.426(4) . ? Li4 O5 1.954(6) . ? C43 O5 1.357(6) . ? O5 C44 1.424(5) . ? C44 C45 1.479(6) . ? C45 O6 1.426(6) . ? O6 C46 1.434(7) . ? 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 N4 Li1 N1 91.6(2) . . ? N4 Li1 N3 96.4(2) . . ? N1 Li1 N3 164.5(3) . . ? N4 Li1 N2 175.3(3) . . ? N1 Li1 N2 88.5(2) . . ? N3 Li1 N2 82.5(2) . . ? N4 Li1 Li3 114.5(3) . . ? N1 Li1 Li3 51.40(18) . . ? N3 Li1 Li3 113.1(3) . . ? N2 Li1 Li3 62.17(19) . . ? N4 Li1 Li4 133.8(3) . . ? N1 Li1 Li4 130.4(3) . . ? N3 Li1 Li4 48.69(17) . . ? N2 Li1 Li4 48.01(17) . . ? Li3 Li1 Li4 107.8(3) . . ? C4 N1 C1 105.7(2) . . ? C4 N1 Li1 121.1(2) . . ? C1 N1 Li1 122.1(3) . . ? C4 N1 Li3 106.5(2) . . ? C1 N1 Li3 119.7(2) . . ? Li1 N1 Li3 79.2(2) . . ? C2 C1 N1 110.1(3) . . ? C2 C1 C20 128.5(3) . . ? N1 C1 C20 121.3(3) . . ? C1 C2 C3 107.3(3) . . ? C4 C3 C2 105.9(3) . . ? N1 C4 C3 111.0(3) . . ? N1 C4 C5 119.9(3) . . ? C3 C4 C5 129.1(3) . . ? C6 C5 C4 107.5(2) . . ? C6 C5 C23 110.6(3) . . ? C4 C5 C23 109.0(2) . . ? C6 C5 C21 109.5(2) . . ? C4 C5 C21 109.6(3) . . ? C23 C5 C21 110.5(3) . . ? C6 N2 C9 107.0(3) . . ? C6 N2 Li4 145.0(3) . . ? C9 N2 Li4 99.5(2) . . ? C6 N2 Li1 111.3(2) . . ? C9 N2 Li1 110.4(2) . . ? Li4 N2 Li1 79.1(2) . . ? C6 N2 Li3 69.0(2) . . ? C9 N2 Li3 75.7(2) . . ? Li4 N2 Li3 141.5(2) . . ? Li1 N2 Li3 67.6(2) . . ? N2 C6 C7 109.7(3) . . ? N2 C6 C5 120.5(3) . . ? C7 C6 C5 128.9(3) . . ? N2 C6 Li3 78.8(2) . . ? C7 C6 Li3 72.5(2) . . ? C5 C6 Li3 107.2(2) . . ? C6 C7 C8 107.2(3) . . ? C6 C7 Li3 74.0(2) . . ? C8 C7 Li3 77.0(2) . . ? C9 C8 C7 106.9(3) . . ? C9 C8 Li3 77.3(2) . . ? C7 C8 Li3 69.5(2) . . ? N2 C9 C8 109.3(3) . . ? N2 C9 C10 119.0(3) . . ? C8 C9 C10 130.7(3) . . ? N2 C9 Li3 72.8(2) . . ? C8 C9 Li3 70.8(2) . . ? C10 C9 Li3 131.8(2) . . ? N2 C9 Li4 49.58(18) . . ? C8 C9 Li4 151.3(3) . . ? C10 C9 Li4 70.3(2) . . ? Li3 C9 Li4 111.9(2) . . ? C11 C10 C9 113.6(2) . . ? C11 C10 N5 105.6(2) . . ? C9 C10 N5 103.5(2) . . ? C11 C10 C25 111.1(3) . . ? C9 C10 C25 110.9(3) . . ? N5 C10 C25 111.8(2) . . ? C11 C10 Li4 74.3(2) . . ? C9 C10 Li4 76.1(2) . . ? N5 C10 Li4 55.20(19) . . ? C25 C10 Li4 166.9(2) . . ? C14 N3 C11 106.2(3) . . ? C14 N3 Li4 141.8(3) . . ? C11 N3 Li4 96.5(2) . . ? C14 N3 Li1 113.4(2) . . ? C11 N3 Li1 117.7(2) . . ? Li4 N3 Li1 80.5(2) . . ? N3 C11 C12 109.8(3) . . ? N3 C11 C10 120.0(3) . . ? C12 C11 C10 129.4(3) . . ? N3 C11 Li4 51.80(19) . . ? C12 C11 Li4 146.0(3) . . ? C10 C11 Li4 71.9(2) . . ? C11 C12 C13 106.6(3) . . ? C14 C13 C12 107.2(3) . . ? N3 C14 C13 110.0(3) . . ? N3 C14 C15 120.2(3) . . ? C13 C14 C15 129.3(3) . . ? C14 C15 C16 106.0(3) . . ? C14 C15 C29 110.9(3) . . ? C16 C15 C29 108.6(3) . . ? C14 C15 C31 110.4(3) . . ? C16 C15 C31 110.6(2) . . ? C29 C15 C31 110.2(3) . . ? C16 N4 C19 106.6(3) . . ? C16 N4 Li1 122.5(2) . . ? C19 N4 Li1 124.5(3) . . ? C16 N4 Li2 73.8(2) . . ? C19 N4 Li2 72.9(2) . . ? Li1 N4 Li2 141.3(3) . . ? N4 C16 C17 110.6(3) . . ? N4 C16 C15 119.2(3) . . ? C17 C16 C15 129.9(3) . . ? N4 C16 Li2 69.9(2) . . ? C17 C16 Li2 74.9(2) . . ? C15 C16 Li2 126.2(3) . . ? C16 C17 C18 106.2(3) . . ? C16 C17 Li2 69.4(2) . . ? C18 C17 Li2 70.8(2) . . ? C19 C18 C17 107.2(3) . . ? C19 C18 Li2 69.6(2) . . ? C17 C18 Li2 73.3(2) . . ? N4 C19 C18 109.4(3) . . ? N4 C19 C20 122.4(3) . . ? C18 C19 C20 128.1(3) . . ? N4 C19 Li2 70.5(2) . . ? C18 C19 Li2 74.1(2) . . ? C20 C19 Li2 120.6(2) . . ? C33 C20 C19 120.0(3) . . ? C33 C20 C1 121.0(3) . . ? C19 C20 C1 119.0(3) . . ? C22 C21 C5 115.9(3) . . ? C24 C23 C5 115.4(3) . . ? C26 C25 C10 115.7(3) . . ? C27 N5 C28 108.8(2) . . ? C27 N5 C10 113.6(3) . . ? C28 N5 C10 113.7(3) . . ? C27 N5 Li4 118.1(2) . . ? C28 N5 Li4 113.5(3) . . ? C10 N5 Li4 88.2(2) . . ? C30 C29 C15 115.2(3) . . ? C32 C31 C15 115.8(3) . . ? C20 C33 C34A 130.8(4) . . ? C20 C33 C34B 133.1(6) . . ? C34A C33 C34B 95.1(6) . . ? O1 Li2 O2 83.6(2) . . ? O1 Li2 N4 111.1(3) . . ? O2 Li2 N4 161.5(3) . . ? O1 Li2 C19 115.5(3) . . ? O2 Li2 C19 147.0(3) . . ? N4 Li2 C19 36.67(14) . . ? O1 Li2 C16 136.4(3) . . ? O2 Li2 C16 125.2(3) . . ? N4 Li2 C16 36.34(14) . . ? C19 Li2 C16 59.71(18) . . ? O1 Li2 C18 144.3(3) . . ? O2 Li2 C18 113.4(3) . . ? N4 Li2 C18 61.27(19) . . ? C19 Li2 C18 36.31(15) . . ? C16 Li2 C18 59.71(18) . . ? O1 Li2 C17 171.7(3) . . ? O2 Li2 C17 103.8(3) . . ? N4 Li2 C17 60.92(18) . . ? C19 Li2 C17 60.07(19) . . ? C16 Li2 C17 35.68(14) . . ? C18 Li2 C17 35.97(15) . . ? C36 O1 C35 112.6(3) . . ? C36 O1 Li2 111.1(3) . . ? C35 O1 Li2 124.4(3) . . ? O1 C36 C37 106.9(4) . . ? O2 C37 C36 108.0(3) . . ? C38 O2 C37 113.0(3) . . ? C38 O2 Li2 127.6(3) . . ? C37 O2 Li2 110.1(3) . . ? O3 Li3 O4 82.6(2) . . ? O3 Li3 N1 111.2(3) . . ? O4 Li3 N1 107.5(3) . . ? O3 Li3 C7 96.1(2) . . ? O4 Li3 C7 145.5(3) . . ? N1 Li3 C7 105.1(3) . . ? O3 Li3 C6 121.3(3) . . ? O4 Li3 C6 154.0(3) . . ? N1 Li3 C6 75.2(2) . . ? C7 Li3 C6 33.50(13) . . ? O3 Li3 C8 103.9(3) . . ? O4 Li3 C8 113.2(3) . . ? N1 Li3 C8 128.7(3) . . ? C7 Li3 C8 33.49(13) . . ? C6 Li3 C8 54.60(16) . . ? O3 Li3 N2 150.5(3) . . ? O4 Li3 N2 121.9(3) . . ? N1 Li3 N2 78.9(2) . . ? C7 Li3 N2 54.48(15) . . ? C6 Li3 N2 32.23(11) . . ? C8 Li3 N2 53.61(15) . . ? O3 Li3 C9 134.6(3) . . ? O4 Li3 C9 103.8(2) . . ? N1 Li3 C9 109.4(3) . . ? C7 Li3 C9 53.77(15) . . ? C6 Li3 C9 52.85(15) . . ? C8 Li3 C9 31.90(12) . . ? N2 Li3 C9 31.49(11) . . ? O3 Li3 Li1 155.6(3) . . ? O4 Li3 Li1 89.6(2) . . ? N1 Li3 Li1 49.40(18) . . ? C7 Li3 Li1 103.2(2) . . ? C6 Li3 Li1 72.4(2) . . ? C8 Li3 Li1 100.4(2) . . ? N2 Li3 Li1 50.25(17) . . ? C9 Li3 Li1 69.70(19) . . ? C40 O3 C39 112.2(3) . . ? C40 O3 Li3 107.3(3) . . ? C39 O3 Li3 113.5(3) . . ? O3 C40 C41 108.8(3) . . ? O4 C41 C40 108.5(3) . . ? C42 O4 C41 113.4(3) . . ? C42 O4 Li3 136.8(3) . . ? C41 O4 Li3 109.7(3) . . ? O5 Li4 N2 129.5(3) . . ? O5 Li4 N3 135.4(3) . . ? N2 Li4 N3 87.8(2) . . ? O5 Li4 N5 110.9(3) . . ? N2 Li4 N5 87.2(2) . . ? N3 Li4 N5 91.7(2) . . ? O5 Li4 C10 147.6(3) . . ? N2 Li4 C10 64.12(18) . . ? N3 Li4 C10 64.10(18) . . ? N5 Li4 C10 36.64(13) . . ? O5 Li4 C11 149.6(3) . . ? N2 Li4 C11 80.6(2) . . ? N3 Li4 C11 31.66(13) . . ? N5 Li4 C11 60.72(17) . . ? C10 Li4 C11 33.80(12) . . ? O5 Li4 C9 147.1(3) . . ? N2 Li4 C9 30.90(12) . . ? N3 Li4 C9 77.5(2) . . ? N5 Li4 C9 58.99(17) . . ? C10 Li4 C9 33.56(12) . . ? C11 Li4 C9 57.38(15) . . ? O5 Li4 Li1 128.7(3) . . ? N2 Li4 Li1 52.87(18) . . ? N3 Li4 Li1 50.81(18) . . ? N5 Li4 Li1 120.2(3) . . ? C10 Li4 Li1 83.6(2) . . ? C11 Li4 Li1 69.37(19) . . ? C9 Li4 Li1 67.43(19) . . ? C43 O5 C44 114.0(4) . . ? C43 O5 Li4 131.0(4) . . ? C44 O5 Li4 113.0(3) . . ? O5 C44 C45 112.6(4) . . ? O6 C45 C44 110.5(4) . . ? C45 O6 C46 114.0(5) . . ? _refine_diff_density_max 1.003 _refine_diff_density_min -0.582 _refine_diff_density_rms 0.091