# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Wenjun Zheng' _publ_contact_author_email WJZHENG@FUDAN.EDU.CN _publ_section_title ; Structural Diversity of 1,2,4-Diazaphospholide Complexes with Alkali Metals ; loop_ _publ_author_name 'Wenjun Zheng.' 'Zhen-Xia Chen.' 'Li Wan.' 'Linghong Wen.' 'Yong Zhang.' # Attachment 'Compound2-CCDC-671979.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 671979' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H52 Li2 N4 O4 P2' _chemical_formula_weight 776.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 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 10.8365(18) _cell_length_b 13.267(2) _cell_length_c 14.755(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.300(4) _cell_angle_gamma 90.00 _cell_volume 2117.8(6) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 867 _cell_measurement_theta_min 2.260 _cell_measurement_theta_max 42.32 _exptl_crystal_description cubic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.148 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9362 _exptl_absorpt_correction_T_max 0.9513 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20390 _diffrn_reflns_av_R_equivalents 0.0528 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3866 _reflns_number_gt 3154 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0635P)^2^+3.4771P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3866 _refine_ls_number_parameters 324 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0928 _refine_ls_R_factor_gt 0.0733 _refine_ls_wR_factor_ref 0.1697 _refine_ls_wR_factor_gt 0.1576 _refine_ls_goodness_of_fit_ref 0.943 _refine_ls_restrained_S_all 0.943 _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 P1 P 0.53442(8) 0.65111(6) 0.25165(5) 0.0393(2) Uani 1 1 d . A . O1 O 0.5313(3) 0.73154(19) 0.62009(16) 0.0686(8) Uani 1 1 d . . . O2 O 0.3174(3) 0.6268(3) 0.53401(19) 0.0947(12) Uani 1 1 d . . . N1 N 0.5694(3) 0.6012(2) 0.42186(17) 0.0475(7) Uani 1 1 d . . . N2 N 0.4859(2) 0.5332(2) 0.38628(16) 0.0437(6) Uani 1 1 d . . . C1 C 0.6044(3) 0.6671(2) 0.3600(2) 0.0401(7) Uani 1 1 d . A . C2 C 0.4549(3) 0.5506(2) 0.29856(19) 0.0357(7) Uani 1 1 d . . . C3 C 0.6960(3) 0.7457(3) 0.3880(2) 0.0477(8) Uani 1 1 d . . . C4 C 0.7008(4) 0.8360(3) 0.3410(2) 0.0589(10) Uani 1 1 d . A . H4 H 0.6428 0.8486 0.2916 0.071 Uiso 1 1 calc R . . C5 C 0.7887(4) 0.9080(4) 0.3652(3) 0.0818(15) Uani 1 1 d . . . H5 H 0.7921 0.9689 0.3316 0.098 Uiso 1 1 calc R A . C6 C 0.8709(4) 0.8916(4) 0.4377(3) 0.0936(18) Uani 1 1 d . A . H6 H 0.9311 0.9412 0.4543 0.112 Uiso 1 1 calc R . . C7 C 0.8666(4) 0.8040(4) 0.4861(3) 0.0872(16) Uani 1 1 d . . . H7 H 0.9230 0.7935 0.5369 0.105 Uiso 1 1 calc R A . C8 C 0.7804(3) 0.7306(4) 0.4612(2) 0.0661(11) Uani 1 1 d . A . H8 H 0.7790 0.6694 0.4946 0.079 Uiso 1 1 calc R . . C9 C 0.3551(3) 0.4905(2) 0.2532(2) 0.0389(7) Uani 1 1 d . A . C10 C 0.2732(3) 0.4357(3) 0.3037(2) 0.0515(8) Uani 1 1 d . . . H10 H 0.2820 0.4371 0.3681 0.062 Uiso 1 1 calc R A . C11 C 0.1796(4) 0.3797(3) 0.2613(3) 0.0657(11) Uani 1 1 d . A . H11 H 0.1254 0.3420 0.2966 0.079 Uiso 1 1 calc R . . C12 C 0.1643(4) 0.3780(3) 0.1681(3) 0.0683(11) Uani 1 1 d . . . H12 H 0.1002 0.3388 0.1390 0.082 Uiso 1 1 calc R A . C13 C 0.2419(4) 0.4332(3) 0.1173(3) 0.0603(10) Uani 1 1 d . A . H13 H 0.2301 0.4340 0.0530 0.072 Uiso 1 1 calc R . . C14 C 0.3378(3) 0.4880(2) 0.1598(2) 0.0474(8) Uani 1 1 d . . . H14 H 0.3926 0.5244 0.1240 0.057 Uiso 1 1 calc R A . C15 C 0.5343(3) 0.8255(2) 0.5835(2) 0.114(6) Uani 0.691(9) 1 d PR A 1 H15A H 0.5127 0.8229 0.5174 0.136 Uiso 0.691(9) 1 calc PR A 1 H15B H 0.6178 0.8552 0.5933 0.136 Uiso 0.691(9) 1 calc PR A 1 C16 C 0.4385(8) 0.8885(5) 0.6323(5) 0.075(2) Uani 0.691(9) 1 d P A 1 H16A H 0.4518 0.9619 0.6251 0.089 Uiso 0.691(9) 1 calc PR A 1 H16B H 0.3526 0.8710 0.6118 0.089 Uiso 0.691(9) 1 calc PR A 1 C17 C 0.4694(13) 0.8549(8) 0.7241(7) 0.090(4) Uani 0.691(9) 1 d P A 1 H17A H 0.3934 0.8470 0.7575 0.108 Uiso 0.691(9) 1 calc PR A 1 H17B H 0.5235 0.9049 0.7565 0.108 Uiso 0.691(9) 1 calc PR A 1 C18 C 0.5352(10) 0.7556(6) 0.7184(5) 0.085(3) Uani 0.691(9) 1 d PU A 1 H18A H 0.6217 0.7612 0.7435 0.102 Uiso 0.691(9) 1 calc PR A 1 H18B H 0.4926 0.7029 0.7523 0.102 Uiso 0.691(9) 1 calc PR A 1 C15' C 0.5267(18) 0.8310(13) 0.5776(12) 0.093(11) Uani 0.309(9) 1 d P A 3 H15C H 0.4469 0.8473 0.5449 0.112 Uiso 0.309(9) 1 calc PR A 3 H15D H 0.5976 0.8464 0.5406 0.112 Uiso 0.309(9) 1 calc PR A 3 C16' C 0.541(2) 0.8740(14) 0.6844(16) 0.118(11) Uani 0.309(9) 1 d P A 3 H16C H 0.6298 0.8842 0.7016 0.141 Uiso 0.309(9) 1 calc PR A 3 H16D H 0.4996 0.9403 0.6872 0.141 Uiso 0.309(9) 1 calc PR A 3 C17' C 0.489(2) 0.807(2) 0.7494(15) 0.091(9) Uani 0.309(9) 1 d P A 3 H17C H 0.4256 0.8414 0.7837 0.109 Uiso 0.309(9) 1 calc PR A 3 H17D H 0.5539 0.7796 0.7926 0.109 Uiso 0.309(9) 1 calc PR A 3 C18' C 0.4324(15) 0.7246(9) 0.6899(8) 0.057(4) Uani 0.309(9) 1 d P A 3 H18C H 0.3487 0.7418 0.6641 0.069 Uiso 0.309(9) 1 calc PR A 3 H18D H 0.4314 0.6583 0.7207 0.069 Uiso 0.309(9) 1 calc PR A 3 C19 C 0.2549(6) 0.6297(7) 0.6171(5) 0.072(3) Uani 0.590(11) 1 d P A 3 H19A H 0.2416 0.6997 0.6375 0.086 Uiso 0.590(11) 1 calc PR A 3 H19B H 0.3004 0.5915 0.6660 0.086 Uiso 0.590(11) 1 calc PR A 3 C20 C 0.1362(10) 0.5794(8) 0.5873(6) 0.069(3) Uani 0.590(11) 1 d P A 3 H20A H 0.0657 0.6138 0.6138 0.082 Uiso 0.590(11) 1 calc PR A 3 H20B H 0.1370 0.5080 0.6069 0.082 Uiso 0.590(11) 1 calc PR A 3 C21 C 0.1251(7) 0.5862(7) 0.4859(6) 0.065(2) Uani 0.590(11) 1 d P A 3 H21A H 0.0447 0.6158 0.4647 0.077 Uiso 0.590(11) 1 calc PR A 3 H21B H 0.1335 0.5189 0.4580 0.077 Uiso 0.590(11) 1 calc PR A 3 C22 C 0.2323(19) 0.6552(14) 0.4630(9) 0.056(3) Uani 0.590(11) 1 d P A 3 H22A H 0.2630 0.6400 0.4026 0.067 Uiso 0.590(11) 1 calc PR A 3 H22B H 0.2098 0.7274 0.4663 0.067 Uiso 0.590(11) 1 calc PR A 3 C19' C 0.2128(12) 0.5577(10) 0.5778(9) 0.071(4) Uani 0.410(11) 1 d P A 4 H19C H 0.2033 0.4915 0.5473 0.086 Uiso 0.410(11) 1 calc PR A 4 H19D H 0.2291 0.5478 0.6439 0.086 Uiso 0.410(11) 1 calc PR A 4 C20' C 0.1039(13) 0.6256(13) 0.5566(13) 0.088(5) Uani 0.410(11) 1 d P A 4 H20C H 0.0258 0.5867 0.5526 0.106 Uiso 0.410(11) 1 calc PR A 4 H20D H 0.0984 0.6785 0.6035 0.106 Uiso 0.410(11) 1 calc PR A 4 C21' C 0.1294(16) 0.670(2) 0.4688(11) 0.147(10) Uani 0.410(11) 1 d P A 4 H21C H 0.0958 0.6262 0.4187 0.176 Uiso 0.410(11) 1 calc PR A 4 H21D H 0.0916 0.7373 0.4622 0.176 Uiso 0.410(11) 1 calc PR A 4 C22' C 0.259(3) 0.676(2) 0.468(2) 0.101(12) Uani 0.410(11) 1 d P A 4 H22C H 0.2853 0.6493 0.4092 0.122 Uiso 0.410(11) 1 calc PR A 4 H22D H 0.2837 0.7479 0.4714 0.122 Uiso 0.410(11) 1 calc PR A 4 Li1 Li 0.4985(5) 0.6052(5) 0.5479(4) 0.0532(14) Uani 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 0.0446(5) 0.0390(4) 0.0346(4) 0.0014(3) 0.0030(3) -0.0023(4) O1 0.106(2) 0.0532(16) 0.0487(14) 0.0038(12) 0.0220(14) 0.0200(15) O2 0.0504(16) 0.176(4) 0.0589(17) 0.028(2) 0.0137(13) 0.0164(19) N1 0.0534(16) 0.0548(17) 0.0346(14) 0.0018(12) 0.0053(12) -0.0179(14) N2 0.0486(15) 0.0494(16) 0.0336(13) -0.0008(12) 0.0057(11) -0.0117(13) C1 0.0408(17) 0.0439(18) 0.0361(16) -0.0037(13) 0.0073(13) -0.0047(14) C2 0.0366(15) 0.0356(16) 0.0353(15) -0.0033(12) 0.0055(12) 0.0046(12) C3 0.0468(18) 0.063(2) 0.0349(16) -0.0077(15) 0.0130(14) -0.0142(16) C4 0.070(2) 0.063(2) 0.0448(19) -0.0063(17) 0.0164(17) -0.0272(19) C5 0.104(3) 0.083(3) 0.062(3) -0.017(2) 0.032(2) -0.056(3) C6 0.088(3) 0.131(5) 0.064(3) -0.037(3) 0.027(2) -0.067(3) C7 0.070(3) 0.137(5) 0.055(2) -0.019(3) 0.001(2) -0.045(3) C8 0.055(2) 0.096(3) 0.047(2) -0.007(2) 0.0034(17) -0.025(2) C9 0.0389(16) 0.0330(16) 0.0445(17) -0.0021(13) 0.0005(13) 0.0028(13) C10 0.055(2) 0.049(2) 0.051(2) 0.0033(16) -0.0003(16) -0.0103(16) C11 0.064(2) 0.059(2) 0.073(3) 0.001(2) 0.001(2) -0.0269(19) C12 0.067(3) 0.058(2) 0.077(3) -0.008(2) -0.014(2) -0.019(2) C13 0.067(2) 0.060(2) 0.053(2) -0.0104(18) -0.0092(18) -0.0039(19) C14 0.053(2) 0.0480(19) 0.0410(17) -0.0022(14) 0.0015(14) -0.0038(15) C15 0.183(12) 0.048(6) 0.121(9) -0.030(5) 0.103(8) -0.058(6) C16 0.087(5) 0.048(3) 0.088(5) 0.002(3) -0.003(4) 0.009(3) C17 0.141(9) 0.072(6) 0.058(6) -0.005(4) 0.013(5) 0.047(6) C18 0.126(8) 0.083(5) 0.044(4) -0.014(3) -0.010(4) 0.038(5) C15' 0.106(17) 0.083(17) 0.086(16) 0.022(12) -0.039(13) 0.052(13) C16' 0.15(2) 0.080(13) 0.130(19) -0.059(13) 0.100(18) -0.066(14) C17' 0.080(14) 0.15(3) 0.043(11) -0.018(14) 0.014(9) -0.043(16) C18' 0.081(10) 0.054(7) 0.040(7) -0.005(5) 0.025(6) -0.002(7) C19 0.057(4) 0.101(7) 0.058(4) -0.010(4) 0.020(3) -0.010(4) C20 0.068(7) 0.066(6) 0.074(6) 0.002(5) 0.021(5) -0.008(5) C21 0.053(4) 0.078(5) 0.063(5) -0.011(4) 0.003(4) -0.010(4) C22 0.069(7) 0.058(7) 0.041(5) 0.008(4) 0.001(4) 0.004(5) C19' 0.062(8) 0.069(8) 0.086(9) 0.006(6) 0.032(7) 0.019(6) C20' 0.053(7) 0.089(11) 0.123(15) -0.001(10) 0.019(8) 0.024(7) C21' 0.089(11) 0.25(3) 0.099(11) 0.077(14) 0.028(8) 0.089(15) C22' 0.10(2) 0.073(15) 0.132(18) 0.025(11) 0.038(14) 0.059(17) Li1 0.056(3) 0.064(4) 0.041(3) 0.007(3) 0.010(2) 0.002(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 C1 1.743(3) . ? P1 C2 1.752(3) . ? O1 C15 1.359(4) . ? O1 C15' 1.460(17) . ? O1 C18 1.483(8) . ? O1 C18' 1.532(11) . ? O1 Li1 2.007(7) . ? O2 C22' 1.31(3) . ? O2 C22 1.406(17) . ? O2 C19 1.434(7) . ? O2 C19' 1.621(13) . ? O2 Li1 1.983(7) . ? N1 C1 1.334(4) . ? N1 N2 1.362(3) . ? N1 Li1 2.053(6) . ? N2 C2 1.338(4) . ? N2 Li1 2.079(7) 3_666 ? N2 Li1 2.565(6) . ? C1 C3 1.482(4) . ? C2 C9 1.473(4) . ? C3 C4 1.387(5) . ? C3 C8 1.390(5) . ? C4 C5 1.381(5) . ? C4 H4 0.9500 . ? C5 C6 1.369(7) . ? C5 H5 0.9500 . ? C6 C7 1.365(7) . ? C6 H6 0.9500 . ? C7 C8 1.384(6) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C14 1.381(4) . ? C9 C10 1.395(4) . ? C10 C11 1.378(5) . ? C10 H10 0.9500 . ? C11 C12 1.376(5) . ? C11 H11 0.9500 . ? C12 C13 1.370(5) . ? C12 H12 0.9500 . ? C13 C14 1.388(5) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.544(8) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.447(11) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.503(12) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C15' C16' 1.68(3) . ? C15' H15C 0.9900 . ? C15' H15D 0.9900 . ? C16' C17' 1.45(3) . ? C16' H16C 0.9900 . ? C16' H16D 0.9900 . ? C17' C18' 1.51(3) . ? C17' H17C 0.9900 . ? C17' H17D 0.9900 . ? C18' H18C 0.9900 . ? C18' H18D 0.9900 . ? C19 C20 1.493(12) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.496(13) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.53(2) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C19' C20' 1.503(17) . ? C19' H19C 0.9900 . ? C19' H19D 0.9900 . ? C20' C21' 1.46(2) . ? C20' H20C 0.9900 . ? C20' H20D 0.9900 . ? C21' C22' 1.41(4) . ? C21' H21C 0.9900 . ? C21' H21D 0.9900 . ? C22' H22C 0.9900 . ? C22' H22D 0.9900 . ? Li1 N2 2.079(7) 3_666 ? Li1 Li1 3.129(13) 3_666 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 P1 C2 85.88(14) . . ? C15 O1 C15' 3.8(7) . . ? C15 O1 C18 101.0(4) . . ? C15' O1 C18 102.9(8) . . ? C15 O1 C18' 110.9(5) . . ? C15' O1 C18' 109.6(10) . . ? C18 O1 C18' 48.5(6) . . ? C15 O1 Li1 124.2(3) . . ? C15' O1 Li1 121.8(7) . . ? C18 O1 Li1 133.8(4) . . ? C18' O1 Li1 101.4(5) . . ? C22' O2 C22 17(2) . . ? C22' O2 C19 113.3(13) . . ? C22 O2 C19 107.9(8) . . ? C22' O2 C19' 105.2(16) . . ? C22 O2 C19' 90.3(9) . . ? C19 O2 C19' 45.5(5) . . ? C22' O2 Li1 125.6(15) . . ? C22 O2 Li1 136.0(8) . . ? C19 O2 Li1 115.4(4) . . ? C19' O2 Li1 126.0(5) . . ? C1 N1 N2 112.3(2) . . ? C1 N1 Li1 137.6(3) . . ? N2 N1 Li1 95.2(2) . . ? C2 N2 N1 112.5(2) . . ? C2 N2 Li1 127.8(3) . 3_666 ? N1 N2 Li1 111.8(2) . 3_666 ? C2 N2 Li1 146.3(2) . . ? N1 N2 Li1 52.85(19) . . ? Li1 N2 Li1 84.0(2) 3_666 . ? N1 C1 C3 118.9(3) . . ? N1 C1 P1 115.0(2) . . ? C3 C1 P1 126.2(2) . . ? N2 C2 C9 118.8(3) . . ? N2 C2 P1 114.3(2) . . ? C9 C2 P1 126.7(2) . . ? C4 C3 C8 118.1(3) . . ? C4 C3 C1 120.8(3) . . ? C8 C3 C1 121.1(3) . . ? C5 C4 C3 120.9(4) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C6 C5 C4 120.0(4) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C7 C6 C5 120.3(4) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 120.1(4) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C7 C8 C3 120.6(4) . . ? C7 C8 H8 119.7 . . ? C3 C8 H8 119.7 . . ? C14 C9 C10 117.8(3) . . ? C14 C9 C2 121.4(3) . . ? C10 C9 C2 120.9(3) . . ? C11 C10 C9 120.9(3) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C12 C11 C10 120.3(4) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C13 C12 C11 119.7(3) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C14 120.0(3) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C9 C14 C13 121.3(3) . . ? C9 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? O1 C15 C16 106.3(3) . . ? O1 C15 H15A 110.5 . . ? C16 C15 H15A 110.5 . . ? O1 C15 H15B 110.5 . . ? C16 C15 H15B 110.5 . . ? H15A C15 H15B 108.7 . . ? C17 C16 C15 98.3(6) . . ? C17 C16 H16A 112.1 . . ? C15 C16 H16A 112.1 . . ? C17 C16 H16B 112.1 . . ? C15 C16 H16B 112.1 . . ? H16A C16 H16B 109.8 . . ? C16 C17 C18 107.6(7) . . ? C16 C17 H17A 110.2 . . ? C18 C17 H17A 110.2 . . ? C16 C17 H17B 110.2 . . ? C18 C17 H17B 110.2 . . ? H17A C17 H17B 108.5 . . ? O1 C18 C17 104.9(5) . . ? O1 C18 H18A 110.8 . . ? C17 C18 H18A 110.8 . . ? O1 C18 H18B 110.8 . . ? C17 C18 H18B 110.8 . . ? H18A C18 H18B 108.9 . . ? O1 C15' C16' 84.5(11) . . ? O1 C15' H15C 114.6 . . ? C16' C15' H15C 114.6 . . ? O1 C15' H15D 114.6 . . ? C16' C15' H15D 114.6 . . ? H15C C15' H15D 111.7 . . ? C17' C16' C15' 113.2(15) . . ? C17' C16' H16C 108.9 . . ? C15' C16' H16C 108.9 . . ? C17' C16' H16D 108.9 . . ? C15' C16' H16D 108.9 . . ? H16C C16' H16D 107.7 . . ? C16' C17' C18' 102.8(16) . . ? C16' C17' H17C 111.2 . . ? C18' C17' H17C 111.2 . . ? C16' C17' H17D 111.2 . . ? C18' C17' H17D 111.2 . . ? H17C C17' H17D 109.1 . . ? C17' C18' O1 94.0(12) . . ? C17' C18' H18C 112.9 . . ? O1 C18' H18C 112.9 . . ? C17' C18' H18D 112.9 . . ? O1 C18' H18D 112.9 . . ? H18C C18' H18D 110.3 . . ? O2 C19 C20 100.2(6) . . ? O2 C19 H19A 111.7 . . ? C20 C19 H19A 111.7 . . ? O2 C19 H19B 111.7 . . ? C20 C19 H19B 111.7 . . ? H19A C19 H19B 109.5 . . ? C19 C20 C21 106.6(7) . . ? C19 C20 H20A 110.4 . . ? C21 C20 H20A 110.4 . . ? C19 C20 H20B 110.4 . . ? C21 C20 H20B 110.4 . . ? H20A C20 H20B 108.6 . . ? C20 C21 C22 103.8(7) . . ? C20 C21 H21A 111.0 . . ? C22 C21 H21A 111.0 . . ? C20 C21 H21B 111.0 . . ? C22 C21 H21B 111.0 . . ? H21A C21 H21B 109.0 . . ? O2 C22 C21 98.5(10) . . ? O2 C22 H22A 112.1 . . ? C21 C22 H22A 112.1 . . ? O2 C22 H22B 112.1 . . ? C21 C22 H22B 112.1 . . ? H22A C22 H22B 109.7 . . ? C20' C19' O2 97.9(9) . . ? C20' C19' H19C 112.2 . . ? O2 C19' H19C 112.2 . . ? C20' C19' H19D 112.2 . . ? O2 C19' H19D 112.2 . . ? H19C C19' H19D 109.8 . . ? C21' C20' C19' 103.7(12) . . ? C21' C20' H20C 111.0 . . ? C19' C20' H20C 111.0 . . ? C21' C20' H20D 111.0 . . ? C19' C20' H20D 111.0 . . ? H20C C20' H20D 109.0 . . ? C22' C21' C20' 105.9(16) . . ? C22' C21' H21C 110.6 . . ? C20' C21' H21C 110.6 . . ? C22' C21' H21D 110.6 . . ? C20' C21' H21D 110.6 . . ? H21C C21' H21D 108.7 . . ? O2 C22' C21' 114(2) . . ? O2 C22' H22C 108.9 . . ? C21' C22' H22C 108.9 . . ? O2 C22' H22D 108.9 . . ? C21' C22' H22D 108.9 . . ? H22C C22' H22D 107.7 . . ? O2 Li1 O1 94.5(3) . . ? O2 Li1 N1 109.2(3) . . ? O1 Li1 N1 116.0(3) . . ? O2 Li1 N2 103.3(3) . 3_666 ? O1 Li1 N2 118.9(3) . 3_666 ? N1 Li1 N2 112.1(3) . 3_666 ? O2 Li1 N2 87.6(2) . . ? O1 Li1 N2 143.4(3) . . ? N1 Li1 N2 31.92(12) . . ? N2 Li1 N2 96.0(2) 3_666 . ? O2 Li1 Li1 96.8(3) . 3_666 ? O1 Li1 Li1 168.1(4) . 3_666 ? N1 Li1 Li1 63.5(2) . 3_666 ? N2 Li1 Li1 54.6(2) 3_666 3_666 ? N2 Li1 Li1 41.35(15) . 3_666 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 C2 -2.4(4) . . . . ? Li1 N1 N2 C2 144.7(3) . . . . ? C1 N1 N2 Li1 149.2(3) . . . 3_666 ? Li1 N1 N2 Li1 -63.7(3) . . . 3_666 ? C1 N1 N2 Li1 -147.1(4) . . . . ? N2 N1 C1 C3 -179.5(3) . . . . ? Li1 N1 C1 C3 54.0(5) . . . . ? N2 N1 C1 P1 0.8(4) . . . . ? Li1 N1 C1 P1 -125.7(3) . . . . ? C2 P1 C1 N1 0.7(2) . . . . ? C2 P1 C1 C3 -179.0(3) . . . . ? N1 N2 C2 C9 -173.2(3) . . . . ? Li1 N2 C2 C9 40.8(4) 3_666 . . . ? Li1 N2 C2 C9 -117.1(4) . . . . ? N1 N2 C2 P1 2.9(3) . . . . ? Li1 N2 C2 P1 -143.1(3) 3_666 . . . ? Li1 N2 C2 P1 59.0(5) . . . . ? C1 P1 C2 N2 -2.0(2) . . . . ? C1 P1 C2 C9 173.8(3) . . . . ? N1 C1 C3 C4 -154.8(3) . . . . ? P1 C1 C3 C4 24.9(5) . . . . ? N1 C1 C3 C8 25.9(5) . . . . ? P1 C1 C3 C8 -154.5(3) . . . . ? C8 C3 C4 C5 1.4(5) . . . . ? C1 C3 C4 C5 -177.9(3) . . . . ? C3 C4 C5 C6 -1.5(6) . . . . ? C4 C5 C6 C7 0.2(7) . . . . ? C5 C6 C7 C8 1.1(7) . . . . ? C6 C7 C8 C3 -1.1(7) . . . . ? C4 C3 C8 C7 -0.1(6) . . . . ? C1 C3 C8 C7 179.2(4) . . . . ? N2 C2 C9 C14 -165.0(3) . . . . ? P1 C2 C9 C14 19.4(4) . . . . ? N2 C2 C9 C10 16.4(4) . . . . ? P1 C2 C9 C10 -159.2(3) . . . . ? C14 C9 C10 C11 1.2(5) . . . . ? C2 C9 C10 C11 179.8(3) . . . . ? C9 C10 C11 C12 -1.0(6) . . . . ? C10 C11 C12 C13 -0.6(6) . . . . ? C11 C12 C13 C14 2.0(6) . . . . ? C10 C9 C14 C13 0.2(5) . . . . ? C2 C9 C14 C13 -178.4(3) . . . . ? C12 C13 C14 C9 -1.8(5) . . . . ? C15' O1 C15 C16 74(13) . . . . ? C18 O1 C15 C16 -46.9(6) . . . . ? C18' O1 C15 C16 2.7(8) . . . . ? Li1 O1 C15 C16 123.6(4) . . . . ? O1 C15 C16 C17 43.9(8) . . . . ? C15 C16 C17 C18 -21.3(11) . . . . ? C15 O1 C18 C17 31.5(9) . . . . ? C15' O1 C18 C17 28.2(12) . . . . ? C18' O1 C18 C17 -76.6(10) . . . . ? Li1 O1 C18 C17 -137.6(7) . . . . ? C16 C17 C18 O1 -4.1(13) . . . . ? C15 O1 C15' C16' -56(13) . . . . ? C18 O1 C15' C16' 4.0(13) . . . . ? C18' O1 C15' C16' 54.2(14) . . . . ? Li1 O1 C15' C16' 171.9(9) . . . . ? O1 C15' C16' C17' -29(2) . . . . ? C15' C16' C17' C18' -4(3) . . . . ? C16' C17' C18' O1 33(2) . . . . ? C15 O1 C18' C17' -59.3(16) . . . . ? C15' O1 C18' C17' -63.2(17) . . . . ? C18 O1 C18' C17' 27.0(14) . . . . ? Li1 O1 C18' C17' 167.0(14) . . . . ? C22' O2 C19 C20 61.1(18) . . . . ? C22 O2 C19 C20 44.2(11) . . . . ? C19' O2 C19 C20 -27.7(7) . . . . ? Li1 O2 C19 C20 -144.2(6) . . . . ? O2 C19 C20 C21 -19.6(10) . . . . ? C19 C20 C21 C22 -8.0(13) . . . . ? C22' O2 C22 C21 -160(7) . . . . ? C19 O2 C22 C21 -48.9(11) . . . . ? C19' O2 C22 C21 -6.1(10) . . . . ? Li1 O2 C22 C21 142.1(8) . . . . ? C20 C21 C22 O2 32.8(13) . . . . ? C22' O2 C19' C20' -29.8(16) . . . . ? C22 O2 C19' C20' -37.2(12) . . . . ? C19 O2 C19' C20' 78.1(11) . . . . ? Li1 O2 C19' C20' 169.7(8) . . . . ? O2 C19' C20' C21' 35.5(17) . . . . ? C19' C20' C21' C22' -31(2) . . . . ? C22 O2 C22' C21' 39(6) . . . . ? C19 O2 C22' C21' -36(3) . . . . ? C19' O2 C22' C21' 12(2) . . . . ? Li1 O2 C22' C21' 172.8(15) . . . . ? C20' C21' C22' O2 11(3) . . . . ? C22' O2 Li1 O1 89.8(17) . . . . ? C22 O2 Li1 O1 107.1(12) . . . . ? C19 O2 Li1 O1 -61.4(6) . . . . ? C19' O2 Li1 O1 -113.5(7) . . . . ? C22' O2 Li1 N1 -29.7(17) . . . . ? C22 O2 Li1 N1 -12.4(13) . . . . ? C19 O2 Li1 N1 179.1(5) . . . . ? C19' O2 Li1 N1 127.0(7) . . . . ? C22' O2 Li1 N2 -149.2(17) . . . 3_666 ? C22 O2 Li1 N2 -131.9(12) . . . 3_666 ? C19 O2 Li1 N2 59.7(6) . . . 3_666 ? C19' O2 Li1 N2 7.5(8) . . . 3_666 ? C22' O2 Li1 N2 -53.6(17) . . . . ? C22 O2 Li1 N2 -36.3(12) . . . . ? C19 O2 Li1 N2 155.2(5) . . . . ? C19' O2 Li1 N2 103.1(7) . . . . ? C22' O2 Li1 Li1 -94.0(17) . . . 3_666 ? C22 O2 Li1 Li1 -76.7(12) . . . 3_666 ? C19 O2 Li1 Li1 114.9(5) . . . 3_666 ? C19' O2 Li1 Li1 62.7(7) . . . 3_666 ? C15 O1 Li1 O2 -78.0(4) . . . . ? C15' O1 Li1 O2 -74.5(10) . . . . ? C18 O1 Li1 O2 89.1(6) . . . . ? C18' O1 Li1 O2 47.2(6) . . . . ? C15 O1 Li1 N1 36.0(5) . . . . ? C15' O1 Li1 N1 39.4(10) . . . . ? C18 O1 Li1 N1 -157.0(6) . . . . ? C18' O1 Li1 N1 161.1(6) . . . . ? C15 O1 Li1 N2 174.2(3) . . . 3_666 ? C15' O1 Li1 N2 177.6(10) . . . 3_666 ? C18 O1 Li1 N2 -18.8(7) . . . 3_666 ? C18' O1 Li1 N2 -60.6(7) . . . 3_666 ? C15 O1 Li1 N2 14.0(7) . . . . ? C15' O1 Li1 N2 17.4(11) . . . . ? C18 O1 Li1 N2 -179.0(6) . . . . ? C18' O1 Li1 N2 139.2(7) . . . . ? C15 O1 Li1 Li1 120.5(17) . . . 3_666 ? C15' O1 Li1 Li1 124.0(19) . . . 3_666 ? C18 O1 Li1 Li1 -72.4(19) . . . 3_666 ? C18' O1 Li1 Li1 -114.3(18) . . . 3_666 ? C1 N1 Li1 O2 81.8(5) . . . . ? N2 N1 Li1 O2 -49.9(4) . . . . ? C1 N1 Li1 O1 -23.3(6) . . . . ? N2 N1 Li1 O1 -155.1(3) . . . . ? C1 N1 Li1 N2 -164.3(3) . . . 3_666 ? N2 N1 Li1 N2 64.0(3) . . . 3_666 ? C1 N1 Li1 N2 131.7(5) . . . . ? C1 N1 Li1 Li1 169.9(3) . . . 3_666 ? N2 N1 Li1 Li1 38.2(2) . . . 3_666 ? C2 N2 Li1 O2 59.5(5) . . . . ? N1 N2 Li1 O2 133.7(3) . . . . ? Li1 N2 Li1 O2 -103.1(3) 3_666 . . . ? C2 N2 Li1 O1 -34.8(8) . . . . ? N1 N2 Li1 O1 39.5(5) . . . . ? Li1 N2 Li1 O1 162.6(6) 3_666 . . . ? C2 N2 Li1 N1 -74.2(4) . . . . ? Li1 N2 Li1 N1 123.2(3) 3_666 . . . ? C2 N2 Li1 N2 162.6(4) . . . 3_666 ? N1 N2 Li1 N2 -123.2(3) . . . 3_666 ? Li1 N2 Li1 N2 0.0 3_666 . . 3_666 ? C2 N2 Li1 Li1 162.6(4) . . . 3_666 ? N1 N2 Li1 Li1 -123.2(3) . . . 3_666 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.343 _refine_diff_density_min -0.435 _refine_diff_density_rms 0.043 # Attachment 'Compound3-CCDC-671980.cif' data_shelxla _database_code_depnum_ccdc_archive 'CCDC 671980' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H40 K2 N4 O2 P2' _chemical_formula_sum 'C36 H40 K2 N4 O2 P2' _chemical_formula_weight 700.86 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' K K 0.2009 0.2494 '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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 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 19.354(3) _cell_length_b 20.082(2) _cell_length_c 11.8003(18) _cell_angle_alpha 90.00 _cell_angle_beta 127.450(2) _cell_angle_gamma 90.00 _cell_volume 3641.1(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6273 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 25.3 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.385 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.670 _exptl_absorpt_correction_T_max 0.871 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17631 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3326 _reflns_number_gt 3054 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _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^)+(0.0275P)^2^+3.2014P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3326 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.0815 _refine_ls_wR_factor_gt 0.0773 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.131 _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 K1 K 0.32342(3) 0.26734(2) -0.07095(4) 0.03352(13) Uani 1 1 d . . . P1 P 0.34091(3) 0.36291(2) 0.35242(5) 0.03131(14) Uani 1 1 d . . . O1 O 0.34794(9) 0.37761(6) -0.17991(15) 0.0384(3) Uani 1 1 d . . . N1 N 0.29482(10) 0.33650(7) 0.09823(16) 0.0302(4) Uani 1 1 d . . . N2 N 0.35305(10) 0.28800(7) 0.18440(16) 0.0304(4) Uani 1 1 d . . . C1 C 0.28174(11) 0.37989(8) 0.16980(18) 0.0235(4) Uani 1 1 d . . . C2 C 0.38362(11) 0.29488(8) 0.32047(18) 0.0244(4) Uani 1 1 d . . . C3 C 0.22101(11) 0.43579(8) 0.09067(18) 0.0232(4) Uani 1 1 d . . . C4 C 0.18080(12) 0.44556(9) -0.05493(19) 0.0292(4) Uani 1 1 d . . . H4 H 0.1945 0.4169 -0.1028 0.035 Uiso 1 1 calc R . . C5 C 0.12120(12) 0.49664(10) -0.1295(2) 0.0334(4) Uani 1 1 d . . . H5 H 0.0937 0.5022 -0.2284 0.040 Uiso 1 1 calc R . . C6 C 0.10146(12) 0.53957(9) -0.0613(2) 0.0329(4) Uani 1 1 d . . . H6 H 0.0609 0.5747 -0.1127 0.039 Uiso 1 1 calc R . . C7 C 0.14120(12) 0.53095(9) 0.0827(2) 0.0299(4) Uani 1 1 d . . . H7 H 0.1278 0.5602 0.1301 0.036 Uiso 1 1 calc R . . C8 C 0.20058(11) 0.47972(8) 0.15778(19) 0.0260(4) Uani 1 1 d . . . H8 H 0.2278 0.4745 0.2567 0.031 Uiso 1 1 calc R . . C9 C 0.44875(11) 0.24639(8) 0.42659(19) 0.0250(4) Uani 1 1 d . . . C10 C 0.49175(12) 0.25613(9) 0.5721(2) 0.0304(4) Uani 1 1 d . . . H10 H 0.4788 0.2944 0.6034 0.036 Uiso 1 1 calc R . . C11 C 0.55309(12) 0.21093(10) 0.6721(2) 0.0331(4) Uani 1 1 d . . . H11 H 0.5813 0.2183 0.7708 0.040 Uiso 1 1 calc R . . C12 C 0.57338(12) 0.15513(9) 0.6288(2) 0.0331(4) Uani 1 1 d . . . H12 H 0.6158 0.1243 0.6973 0.040 Uiso 1 1 calc R . . C13 C 0.53127(12) 0.14459(9) 0.4845(2) 0.0336(4) Uani 1 1 d . . . H13 H 0.5447 0.1063 0.4540 0.040 Uiso 1 1 calc R . . C14 C 0.46985(12) 0.18955(9) 0.3846(2) 0.0310(4) Uani 1 1 d . . . H14 H 0.4415 0.1817 0.2861 0.037 Uiso 1 1 calc R . . C15 C 0.32378(15) 0.37620(11) -0.3203(2) 0.0434(5) Uani 1 1 d . . . H15A H 0.3749 0.3647 -0.3166 0.052 Uiso 1 1 calc R . . H15B H 0.3024 0.4206 -0.3653 0.052 Uiso 1 1 calc R . . C16 C 0.25327(16) 0.32500(11) -0.4066(2) 0.0508(6) Uani 1 1 d . . . H16A H 0.2758 0.2809 -0.3642 0.076 Uiso 1 1 calc R . . H16B H 0.2344 0.3250 -0.5048 0.076 Uiso 1 1 calc R . . H16C H 0.2037 0.3358 -0.4070 0.076 Uiso 1 1 calc R . . C17 C 0.41063(14) 0.42862(10) -0.0946(2) 0.0436(5) Uani 1 1 d . . . H17A H 0.3868 0.4726 -0.1403 0.052 Uiso 1 1 calc R . . H17B H 0.4641 0.4205 -0.0861 0.052 Uiso 1 1 calc R . . C18 C 0.43181(17) 0.42822(13) 0.0507(3) 0.0613(7) Uani 1 1 d . . . H18A H 0.3786 0.4359 0.0414 0.092 Uiso 1 1 calc R . . H18B H 0.4739 0.4635 0.1092 0.092 Uiso 1 1 calc R . . H18C H 0.4567 0.3850 0.0963 0.092 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 K1 0.0434(3) 0.0314(2) 0.0358(3) -0.00138(18) 0.0293(2) 0.00198(18) P1 0.0350(3) 0.0342(3) 0.0238(3) 0.0027(2) 0.0174(2) 0.0112(2) O1 0.0434(8) 0.0341(7) 0.0396(8) -0.0022(6) 0.0262(7) -0.0049(6) N1 0.0343(8) 0.0284(8) 0.0262(8) 0.0015(7) 0.0176(7) 0.0062(7) N2 0.0331(8) 0.0285(8) 0.0278(8) 0.0017(7) 0.0176(7) 0.0067(7) C1 0.0215(9) 0.0259(9) 0.0241(9) -0.0011(7) 0.0144(8) -0.0019(7) C2 0.0234(9) 0.0240(9) 0.0267(9) 0.0000(7) 0.0157(8) -0.0007(7) C3 0.0212(8) 0.0240(9) 0.0262(9) 0.0000(7) 0.0153(8) -0.0024(7) C4 0.0297(10) 0.0329(10) 0.0276(10) 0.0014(8) 0.0188(8) 0.0036(8) C5 0.0336(10) 0.0417(11) 0.0258(10) 0.0075(8) 0.0185(9) 0.0056(9) C6 0.0300(10) 0.0320(10) 0.0340(11) 0.0061(8) 0.0180(9) 0.0076(8) C7 0.0319(10) 0.0279(9) 0.0345(10) -0.0008(8) 0.0226(9) 0.0021(8) C8 0.0266(9) 0.0271(9) 0.0233(9) -0.0012(7) 0.0147(8) -0.0017(7) C9 0.0222(9) 0.0253(9) 0.0301(10) 0.0013(7) 0.0174(8) -0.0017(7) C10 0.0311(10) 0.0310(10) 0.0328(11) 0.0018(8) 0.0214(9) 0.0052(8) C11 0.0309(10) 0.0402(11) 0.0295(10) 0.0073(8) 0.0191(9) 0.0043(8) C12 0.0273(10) 0.0316(10) 0.0417(12) 0.0121(9) 0.0217(9) 0.0050(8) C13 0.0298(10) 0.0281(10) 0.0448(12) 0.0009(9) 0.0237(9) 0.0038(8) C14 0.0292(10) 0.0311(10) 0.0321(10) -0.0009(8) 0.0183(9) 0.0000(8) C15 0.0523(13) 0.0426(12) 0.0421(12) 0.0076(10) 0.0323(11) 0.0091(10) C16 0.0631(15) 0.0402(12) 0.0411(13) -0.0037(10) 0.0274(12) 0.0030(11) C17 0.0400(12) 0.0381(11) 0.0535(14) -0.0030(10) 0.0287(11) -0.0062(9) C18 0.0597(16) 0.0693(17) 0.0568(15) -0.0241(13) 0.0365(14) -0.0287(13) _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 K1 N2 2.7348(16) . ? K1 O1 2.7430(14) . ? K1 N1 2.7504(15) . ? K1 N1 2.9653(16) 7 ? K1 N2 3.0220(17) 7 ? K1 C12 3.3450(18) 2_655 ? K1 C1 3.3700(17) 7 ? K1 C13 3.3966(19) 2_655 ? K1 C11 3.4477(19) 2_655 ? K1 C2 3.4552(18) 7 ? K1 K1 4.1418(9) 7 ? P1 C1 1.7523(18) . ? P1 C2 1.7523(17) . ? O1 C15 1.422(2) . ? O1 C17 1.432(2) . ? N1 C1 1.340(2) . ? N1 N2 1.363(2) . ? N1 K1 2.9653(16) 7 ? N2 C2 1.339(2) . ? N2 K1 3.0220(17) 7 ? C1 C3 1.476(2) . ? C1 K1 3.3700(17) 7 ? C2 C9 1.478(2) . ? C2 K1 3.4552(18) 7 ? C3 C8 1.394(2) . ? C3 C4 1.404(2) . ? C4 C5 1.387(3) . ? C4 H4 0.9500 . ? C5 C6 1.382(3) . ? C5 H5 0.9500 . ? C6 C7 1.385(3) . ? C6 H6 0.9500 . ? C7 C8 1.388(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.393(3) . ? C9 C14 1.400(2) . ? C10 C11 1.386(3) . ? C10 H10 0.9500 . ? C11 C12 1.384(3) . ? C11 K1 3.4477(19) 2_655 ? C11 H11 0.9500 . ? C12 C13 1.386(3) . ? C12 K1 3.3450(18) 2_655 ? C12 H12 0.9500 . ? C13 C14 1.383(3) . ? C13 K1 3.3966(19) 2_655 ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.506(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.501(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? 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 K1 O1 114.44(5) . . ? N2 K1 N1 28.78(4) . . ? O1 K1 N1 95.80(4) . . ? N2 K1 N1 81.79(4) . 7 ? O1 K1 N1 149.19(4) . 7 ? N1 K1 N1 87.20(5) . 7 ? N2 K1 N2 88.12(5) . 7 ? O1 K1 N2 124.08(4) . 7 ? N1 K1 N2 80.51(4) . 7 ? N1 K1 N2 26.30(4) 7 7 ? N2 K1 C12 125.15(5) . 2_655 ? O1 K1 C12 98.82(5) . 2_655 ? N1 K1 C12 153.75(5) . 2_655 ? N1 K1 C12 91.22(4) 7 2_655 ? N2 K1 C12 108.43(4) 7 2_655 ? N2 K1 C1 101.09(4) . 7 ? O1 K1 C1 141.84(4) . 7 ? N1 K1 C1 110.39(5) . 7 ? N1 K1 C1 23.32(4) 7 7 ? N2 K1 C1 40.71(4) 7 7 ? C12 K1 C1 69.41(4) 2_655 7 ? N2 K1 C13 101.45(5) . 2_655 ? O1 K1 C13 112.28(5) . 2_655 ? N1 K1 C13 130.07(5) . 2_655 ? N1 K1 C13 88.03(4) 7 2_655 ? N2 K1 C13 111.87(4) 7 2_655 ? C12 K1 C13 23.71(5) 2_655 2_655 ? C1 K1 C13 71.51(4) 7 2_655 ? N2 K1 C11 134.92(5) . 2_655 ? O1 K1 C11 75.47(5) . 2_655 ? N1 K1 C11 154.81(5) . 2_655 ? N1 K1 C11 112.53(4) 7 2_655 ? N2 K1 C11 124.09(4) 7 2_655 ? C12 K1 C11 23.45(5) 2_655 2_655 ? C1 K1 C11 89.54(4) 7 2_655 ? C13 K1 C11 40.88(5) 2_655 2_655 ? N2 K1 C2 110.57(5) . 7 ? O1 K1 C2 109.51(4) . 7 ? N1 K1 C2 99.21(5) . 7 ? N1 K1 C2 40.06(4) 7 7 ? N2 K1 C2 22.61(4) 7 7 ? C12 K1 C2 96.29(4) 2_655 7 ? C1 K1 C2 40.93(4) 7 7 ? C13 K1 C2 108.24(4) 2_655 7 ? C11 K1 C2 105.97(4) 2_655 7 ? N2 K1 K1 46.82(3) . 7 ? O1 K1 K1 133.01(3) . 7 ? N1 K1 K1 45.65(3) . 7 ? N1 K1 K1 41.55(3) 7 7 ? N2 K1 K1 41.30(3) 7 7 ? C12 K1 K1 127.65(4) 2_655 7 ? C1 K1 K1 64.78(3) 7 7 ? C13 K1 K1 113.76(4) 2_655 7 ? C11 K1 K1 151.07(4) 2_655 7 ? C2 K1 K1 63.79(3) 7 7 ? C1 P1 C2 85.88(8) . . ? C15 O1 C17 111.78(16) . . ? C15 O1 K1 120.13(11) . . ? C17 O1 K1 124.22(12) . . ? C1 N1 N2 112.43(14) . . ? C1 N1 K1 169.76(12) . . ? N2 N1 K1 74.97(9) . . ? C1 N1 K1 95.54(10) . 7 ? N2 N1 K1 79.17(9) . 7 ? K1 N1 K1 92.80(5) . 7 ? C2 N2 N1 112.52(14) . . ? C2 N2 K1 168.77(12) . . ? N1 N2 K1 76.24(9) . . ? C2 N2 K1 97.20(11) . 7 ? N1 N2 K1 74.53(9) . 7 ? K1 N2 K1 91.88(5) . 7 ? N1 C1 C3 118.60(15) . . ? N1 C1 P1 114.57(13) . . ? C3 C1 P1 126.83(13) . . ? N1 C1 K1 61.14(9) . 7 ? C3 C1 K1 111.54(10) . 7 ? P1 C1 K1 93.47(7) . 7 ? N2 C2 C9 118.38(15) . . ? N2 C2 P1 114.59(13) . . ? C9 C2 P1 127.02(13) . . ? N2 C2 K1 60.19(9) . 7 ? C9 C2 K1 115.69(10) . 7 ? P1 C2 K1 90.63(6) . 7 ? C8 C3 C4 117.99(16) . . ? C8 C3 C1 120.92(15) . . ? C4 C3 C1 121.07(15) . . ? C5 C4 C3 120.55(17) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C6 C5 C4 120.65(17) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 119.48(17) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C6 C7 C8 120.19(17) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C7 C8 C3 121.14(16) . . ? C7 C8 H8 119.4 . . ? C3 C8 H8 119.4 . . ? C10 C9 C14 117.78(16) . . ? C10 C9 C2 120.94(16) . . ? C14 C9 C2 121.28(16) . . ? C11 C10 C9 121.16(17) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C12 C11 C10 120.30(18) . . ? C12 C11 K1 74.11(10) . 2_655 ? C10 C11 K1 84.59(11) . 2_655 ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? K1 C11 H11 111.7 2_655 . ? C11 C12 C13 119.37(17) . . ? C11 C12 K1 82.44(11) . 2_655 ? C13 C12 K1 80.23(11) . 2_655 ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? K1 C12 H12 107.4 2_655 . ? C14 C13 C12 120.37(18) . . ? C14 C13 K1 84.71(11) . 2_655 ? C12 C13 K1 76.06(11) . 2_655 ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? K1 C13 H13 109.6 2_655 . ? C13 C14 C9 121.02(18) . . ? C13 C14 H14 119.5 . . ? C9 C14 H14 119.5 . . ? O1 C15 C16 108.81(17) . . ? O1 C15 H15A 109.9 . . ? C16 C15 H15A 109.9 . . ? O1 C15 H15B 109.9 . . ? C16 C15 H15B 109.9 . . ? H15A C15 H15B 108.3 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O1 C17 C18 108.98(17) . . ? O1 C17 H17A 109.9 . . ? C18 C17 H17A 109.9 . . ? O1 C17 H17B 109.9 . . ? C18 C17 H17B 109.9 . . ? H17A C17 H17B 108.3 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 K1 O1 C15 -171.68(13) . . . . ? N1 K1 O1 C15 -148.83(13) . . . . ? N1 K1 O1 C15 -54.55(17) 7 . . . ? N2 K1 O1 C15 -66.37(14) 7 . . . ? C12 K1 O1 C15 53.04(14) 2_655 . . . ? C1 K1 O1 C15 -14.71(16) 7 . . . ? C13 K1 O1 C15 73.37(14) 2_655 . . . ? C11 K1 O1 C15 55.21(13) 2_655 . . . ? C2 K1 O1 C15 -46.89(14) 7 . . . ? K1 K1 O1 C15 -118.83(13) 7 . . . ? N2 K1 O1 C17 32.31(15) . . . . ? N1 K1 O1 C17 55.16(14) . . . . ? N1 K1 O1 C17 149.44(13) 7 . . . ? N2 K1 O1 C17 137.62(14) 7 . . . ? C12 K1 O1 C17 -102.96(14) 2_655 . . . ? C1 K1 O1 C17 -170.72(13) 7 . . . ? C13 K1 O1 C17 -82.64(15) 2_655 . . . ? C11 K1 O1 C17 -100.80(14) 2_655 . . . ? C2 K1 O1 C17 157.10(14) 7 . . . ? K1 K1 O1 C17 85.17(15) 7 . . . ? N2 K1 N1 C1 137.4(7) . . . . ? O1 K1 N1 C1 4.7(7) . . . . ? N1 K1 N1 C1 -144.6(7) 7 . . . ? N2 K1 N1 C1 -119.0(7) 7 . . . ? C12 K1 N1 C1 128.4(6) 2_655 . . . ? C1 K1 N1 C1 -147.1(7) 7 . . . ? C13 K1 N1 C1 130.4(7) 2_655 . . . ? C11 K1 N1 C1 72.6(7) 2_655 . . . ? C2 K1 N1 C1 -106.2(7) 7 . . . ? K1 K1 N1 C1 -144.6(7) 7 . . . ? O1 K1 N1 N2 -132.76(10) . . . . ? N1 K1 N1 N2 78.00(9) 7 . . . ? N2 K1 N1 N2 103.60(9) 7 . . . ? C12 K1 N1 N2 -9.09(16) 2_655 . . . ? C1 K1 N1 N2 75.49(10) 7 . . . ? C13 K1 N1 N2 -7.07(12) 2_655 . . . ? C11 K1 N1 N2 -64.88(15) 2_655 . . . ? C2 K1 N1 N2 116.35(10) 7 . . . ? K1 K1 N1 N2 78.00(9) 7 . . . ? N2 K1 N1 K1 -78.00(9) . . . 7 ? O1 K1 N1 K1 149.25(4) . . . 7 ? N1 K1 N1 K1 0.0 7 . . 7 ? N2 K1 N1 K1 25.60(4) 7 . . 7 ? C12 K1 N1 K1 -87.08(11) 2_655 . . 7 ? C1 K1 N1 K1 -2.51(5) 7 . . 7 ? C13 K1 N1 K1 -85.06(6) 2_655 . . 7 ? C11 K1 N1 K1 -142.87(10) 2_655 . . 7 ? C2 K1 N1 K1 38.35(4) 7 . . 7 ? C1 N1 N2 C2 0.1(2) . . . . ? K1 N1 N2 C2 172.60(14) . . . . ? K1 N1 N2 C2 -91.49(13) 7 . . . ? C1 N1 N2 K1 -172.53(14) . . . . ? K1 N1 N2 K1 95.90(3) 7 . . . ? C1 N1 N2 K1 91.57(13) . . . 7 ? K1 N1 N2 K1 -95.90(4) . . . 7 ? O1 K1 N2 C2 -89.0(6) . . . . ? N1 K1 N2 C2 -142.3(7) . . . . ? N1 K1 N2 C2 118.4(6) 7 . . . ? N2 K1 N2 C2 144.1(6) 7 . . . ? C12 K1 N2 C2 32.8(6) 2_655 . . . ? C1 K1 N2 C2 105.3(6) 7 . . . ? C13 K1 N2 C2 32.1(6) 2_655 . . . ? C11 K1 N2 C2 4.7(7) 2_655 . . . ? C2 K1 N2 C2 146.8(6) 7 . . . ? K1 K1 N2 C2 144.1(6) 7 . . . ? O1 K1 N2 N1 53.36(10) . . . . ? N1 K1 N2 N1 -99.22(9) 7 . . . ? N2 K1 N2 N1 -73.57(9) 7 . . . ? C12 K1 N2 N1 175.10(9) 2_655 . . . ? C1 K1 N2 N1 -112.38(9) 7 . . . ? C13 K1 N2 N1 174.49(9) 2_655 . . . ? C11 K1 N2 N1 147.03(9) 2_655 . . . ? C2 K1 N2 N1 -70.86(10) 7 . . . ? K1 K1 N2 N1 -73.57(9) 7 . . . ? O1 K1 N2 K1 126.93(4) . . . 7 ? N1 K1 N2 K1 73.57(9) . . . 7 ? N1 K1 N2 K1 -25.64(4) 7 . . 7 ? N2 K1 N2 K1 0.0 7 . . 7 ? C12 K1 N2 K1 -111.33(5) 2_655 . . 7 ? C1 K1 N2 K1 -38.80(4) 7 . . 7 ? C13 K1 N2 K1 -111.94(4) 2_655 . . 7 ? C11 K1 N2 K1 -139.39(6) 2_655 . . 7 ? C2 K1 N2 K1 2.71(5) 7 . . 7 ? N2 N1 C1 C3 179.26(14) . . . . ? K1 N1 C1 C3 44.2(7) . . . . ? K1 N1 C1 C3 -100.20(14) 7 . . . ? N2 N1 C1 P1 -0.69(19) . . . . ? K1 N1 C1 P1 -135.7(6) . . . . ? K1 N1 C1 P1 79.86(11) 7 . . . ? N2 N1 C1 K1 -80.55(13) . . . 7 ? K1 N1 C1 K1 144.4(7) . . . 7 ? C2 P1 C1 N1 0.82(13) . . . . ? C2 P1 C1 C3 -179.12(15) . . . . ? C2 P1 C1 K1 60.55(7) . . . 7 ? N1 N2 C2 C9 -178.84(14) . . . . ? K1 N2 C2 C9 -38.8(7) . . . . ? K1 N2 C2 C9 104.97(14) 7 . . . ? N1 N2 C2 P1 0.6(2) . . . . ? K1 N2 C2 P1 140.6(6) . . . . ? K1 N2 C2 P1 -75.62(11) 7 . . . ? N1 N2 C2 K1 76.19(13) . . . 7 ? K1 N2 C2 K1 -143.8(6) . . . 7 ? C1 P1 C2 N2 -0.77(14) . . . . ? C1 P1 C2 C9 178.58(16) . . . . ? C1 P1 C2 K1 -57.97(6) . . . 7 ? N1 C1 C3 C8 175.65(16) . . . . ? P1 C1 C3 C8 -4.4(2) . . . . ? K1 C1 C3 C8 107.73(15) 7 . . . ? N1 C1 C3 C4 -3.1(2) . . . . ? P1 C1 C3 C4 176.85(13) . . . . ? K1 C1 C3 C4 -71.02(17) 7 . . . ? C8 C3 C4 C5 -1.4(3) . . . . ? C1 C3 C4 C5 177.39(16) . . . . ? C3 C4 C5 C6 1.1(3) . . . . ? C4 C5 C6 C7 -0.5(3) . . . . ? C5 C6 C7 C8 0.2(3) . . . . ? C6 C7 C8 C3 -0.5(3) . . . . ? C4 C3 C8 C7 1.1(3) . . . . ? C1 C3 C8 C7 -177.72(16) . . . . ? N2 C2 C9 C10 171.05(16) . . . . ? P1 C2 C9 C10 -8.3(2) . . . . ? K1 C2 C9 C10 -120.49(15) 7 . . . ? N2 C2 C9 C14 -8.4(2) . . . . ? P1 C2 C9 C14 172.24(14) . . . . ? K1 C2 C9 C14 60.03(19) 7 . . . ? C14 C9 C10 C11 -0.3(3) . . . . ? C2 C9 C10 C11 -179.78(16) . . . . ? C9 C10 C11 C12 0.5(3) . . . . ? C9 C10 C11 K1 68.56(17) . . . 2_655 ? C10 C11 C12 C13 -0.5(3) . . . . ? K1 C11 C12 C13 -74.28(16) 2_655 . . . ? C10 C11 C12 K1 73.74(17) . . . 2_655 ? C11 C12 C13 C14 0.3(3) . . . . ? K1 C12 C13 C14 -75.20(17) 2_655 . . . ? C11 C12 C13 K1 75.52(16) . . . 2_655 ? C12 C13 C14 C9 -0.1(3) . . . . ? K1 C13 C14 C9 -70.55(16) 2_655 . . . ? C10 C9 C14 C13 0.1(3) . . . . ? C2 C9 C14 C13 179.57(16) . . . . ? C17 O1 C15 C16 -175.92(17) . . . . ? K1 O1 C15 C16 25.3(2) . . . . ? C15 O1 C17 C18 178.87(18) . . . . ? K1 O1 C17 C18 -23.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.217 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.040 # Attachment 'Compound5-CCDC-671981.cif' data_f60829a _database_code_depnum_ccdc_archive 'CCDC 671981' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H44 K2 N4 O3 P2' _chemical_formula_weight 576.77 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' K K 0.2009 0.2494 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.350(4) _cell_length_b 14.531(5) _cell_length_c 20.237(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.272(5) _cell_angle_gamma 90.00 _cell_volume 3337(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.148 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 0.408 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9229 _exptl_absorpt_correction_T_max 0.9414 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 13743 _diffrn_reflns_av_R_equivalents 0.0527 _diffrn_reflns_av_sigmaI/netI 0.0538 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5864 _reflns_number_gt 3636 _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^)+(0.0824P)^2^+0.6276P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5864 _refine_ls_number_parameters 431 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0783 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1351 _refine_ls_wR_factor_gt 0.1171 _refine_ls_goodness_of_fit_ref 0.827 _refine_ls_restrained_S_all 0.829 _refine_ls_shift/su_max 0.006 _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 K1 K 0.12093(6) 0.58767(4) 0.74497(3) 0.0633(2) Uani 1 1 d . . 4 K2 K 0.10006(8) 0.58239(5) 0.94375(3) 0.0781(2) Uani 1 1 d . . 4 P1 P 0.26067(10) 0.79815(7) 0.93663(5) 0.0926(3) Uani 1 1 d . . 4 P2 P 0.01471(7) 0.38728(5) 0.87353(3) 0.0560(2) Uani 1 1 d . A 4 N1 N 0.1326(2) 0.71677(16) 0.84710(11) 0.0638(6) Uani 1 1 d . . 4 N2 N 0.2401(2) 0.67415(16) 0.84614(12) 0.0654(6) Uani 1 1 d . . 4 N3 N -0.1104(2) 0.25214(17) 0.82717(12) 0.0682(6) Uani 1 1 d . . 4 N4 N 0.0135(2) 0.21861(16) 0.83254(12) 0.0686(7) Uani 1 1 d . . 4 O2 O 0.0553(2) 0.46399(13) 0.83212(9) 0.0752(6) Uani 1 1 d . A 4 O3 O 0.0123(2) 0.40399(13) 0.94602(9) 0.0741(6) Uani 1 1 d . . 4 C1 C 0.0157(4) 0.8364(3) 0.89835(18) 0.0896(11) Uani 0.640(14) 1 d P . 1 C2 C -0.0050(11) 0.8934(10) 0.8401(6) 0.146(8) Uani 0.640(14) 1 d P . 1 H2A H -0.0777 0.9264 0.8444 0.219 Uiso 0.640(14) 1 calc PR . 1 H2B H -0.0097 0.8550 0.8015 0.219 Uiso 0.640(14) 1 calc PR . 1 H2C H 0.0587 0.9364 0.8359 0.219 Uiso 0.640(14) 1 calc PR . 1 C3 C 0.0081(14) 0.8837(10) 0.9639(6) 0.154(7) Uani 0.640(14) 1 d P . 1 H3A H 0.0222 0.8399 0.9987 0.231 Uiso 0.640(14) 1 calc PR . 1 H3B H -0.0689 0.9099 0.9683 0.231 Uiso 0.640(14) 1 calc PR . 1 H3C H 0.0663 0.9316 0.9668 0.231 Uiso 0.640(14) 1 calc PR . 1 C4 C -0.0919(6) 0.7645(6) 0.9013(6) 0.113(3) Uani 0.640(14) 1 d P . 1 H4A H -0.0819 0.7258 0.9394 0.170 Uiso 0.640(14) 1 calc PR . 1 H4B H -0.0933 0.7273 0.8621 0.170 Uiso 0.640(14) 1 calc PR . 1 H4C H -0.1648 0.7976 0.9041 0.170 Uiso 0.640(14) 1 calc PR . 1 C1' C 0.0157(4) 0.8364(3) 0.89835(18) 0.0896(11) Uani 0.360(14) 1 d P . 2 C2' C 0.061(2) 0.9477(10) 0.8906(15) 0.165(10) Uani 0.360(14) 1 d P . 2 H2'1 H 0.1217 0.9605 0.9233 0.247 Uiso 0.360(14) 1 calc PR . 2 H2'2 H -0.0041 0.9883 0.8968 0.247 Uiso 0.360(14) 1 calc PR . 2 H2'3 H 0.0922 0.9569 0.8473 0.247 Uiso 0.360(14) 1 calc PR . 2 C3' C -0.015(3) 0.836(2) 0.9664(14) 0.21(2) Uani 0.360(14) 1 d P . 2 H3'1 H 0.0540 0.8241 0.9933 0.318 Uiso 0.360(14) 1 calc PR . 2 H3'2 H -0.0727 0.7891 0.9737 0.318 Uiso 0.360(14) 1 calc PR . 2 H3'3 H -0.0471 0.8950 0.9779 0.318 Uiso 0.360(14) 1 calc PR . 2 C4' C -0.065(2) 0.828(3) 0.8464(14) 0.26(3) Uani 0.360(14) 1 d P . 2 H4'1 H -0.0240 0.8270 0.8054 0.396 Uiso 0.360(14) 1 calc PR . 2 H4'2 H -0.1184 0.8791 0.8466 0.396 Uiso 0.360(14) 1 calc PR . 2 H4'3 H -0.1083 0.7716 0.8510 0.396 Uiso 0.360(14) 1 calc PR . 2 C5 C 0.1301(3) 0.7834(2) 0.89132(14) 0.0676(8) Uani 1 1 d . . . C6 C 0.3166(3) 0.7089(2) 0.88914(15) 0.0694(8) Uani 1 1 d . . . C7 C 0.4386(3) 0.6668(3) 0.8922(2) 0.0993(12) Uani 1 1 d . . . C8 C 0.4274(5) 0.5663(4) 0.9100(4) 0.193(3) Uani 1 1 d . . . H8A H 0.5041 0.5385 0.9116 0.290 Uiso 1 1 calc R . . H8B H 0.3790 0.5357 0.8773 0.290 Uiso 1 1 calc R . . H8C H 0.3919 0.5608 0.9524 0.290 Uiso 1 1 calc R . . C9 C 0.4993(4) 0.6806(5) 0.8287(3) 0.170(3) Uani 1 1 d . . . H9A H 0.5763 0.6534 0.8315 0.255 Uiso 1 1 calc R . . H9B H 0.5064 0.7453 0.8200 0.255 Uiso 1 1 calc R . . H9C H 0.4544 0.6520 0.7936 0.255 Uiso 1 1 calc R . . C10 C 0.5106(3) 0.7119(2) 0.94848(15) 0.214(4) Uani 1 1 d . . . H10A H 0.5885 0.6862 0.9501 0.322 Uiso 1 1 calc R . . H10B H 0.4729 0.7008 0.9897 0.322 Uiso 1 1 calc R . . H10C H 0.5154 0.7770 0.9409 0.322 Uiso 1 1 calc R . . C11 C -0.2410(3) 0.3813(2) 0.83821(15) 0.0841(10) Uani 0.439(17) 1 d PR A 1 C12 C -0.2966(3) 0.3910(2) 0.90107(15) 0.130(8) Uani 0.439(17) 1 d PR A 1 H12A H -0.3715 0.4210 0.8949 0.195 Uiso 0.439(17) 1 d PR A 1 H12B H -0.2473 0.4272 0.9301 0.195 Uiso 0.439(17) 1 d PR A 1 H12C H -0.3083 0.3313 0.9201 0.195 Uiso 0.439(17) 1 d PR A 1 C13 C -0.3284(17) 0.3241(18) 0.7889(10) 0.156(9) Uani 0.439(17) 1 d P A 1 H13A H -0.2923 0.3172 0.7467 0.234 Uiso 0.439(17) 1 calc PR A 1 H13B H -0.4015 0.3567 0.7833 0.234 Uiso 0.439(17) 1 calc PR A 1 H13C H -0.3432 0.2644 0.8073 0.234 Uiso 0.439(17) 1 calc PR A 1 C14 C -0.232(3) 0.4787(13) 0.7997(16) 0.154(10) Uani 0.439(17) 1 d P A 1 H14A H -0.1926 0.4697 0.7586 0.231 Uiso 0.439(17) 1 calc PR A 1 H14B H -0.1877 0.5216 0.8265 0.231 Uiso 0.439(17) 1 calc PR A 1 H14C H -0.3095 0.5025 0.7911 0.231 Uiso 0.439(17) 1 calc PR A 1 C11' C -0.2410(3) 0.3813(2) 0.83821(15) 0.0841(10) Uani 0.561(17) 1 d P A 2 C12' C -0.2509(12) 0.4418(13) 0.9028(7) 0.194(8) Uani 0.561(17) 1 d P A 2 H12D H -0.2559 0.4022 0.9406 0.291 Uiso 0.561(17) 1 calc PR A 2 H12E H -0.3202 0.4795 0.8995 0.291 Uiso 0.561(17) 1 calc PR A 2 H12F H -0.1825 0.4803 0.9074 0.291 Uiso 0.561(17) 1 calc PR A 2 C13' C -0.3389(10) 0.3112(12) 0.8368(10) 0.157(7) Uani 0.561(17) 1 d P A 2 H13D H -0.3345 0.2748 0.8764 0.236 Uiso 0.561(17) 1 calc PR A 2 H13E H -0.3310 0.2721 0.7990 0.236 Uiso 0.561(17) 1 calc PR A 2 H13F H -0.4136 0.3423 0.8343 0.236 Uiso 0.561(17) 1 calc PR A 2 C14' C -0.2415(16) 0.4330(15) 0.7797(12) 0.160(8) Uani 0.561(17) 1 d P A 2 H14D H -0.3164 0.4629 0.7739 0.240 Uiso 0.561(17) 1 calc PR A 2 H14E H -0.2280 0.3930 0.7429 0.240 Uiso 0.561(17) 1 calc PR A 2 H14F H -0.1803 0.4786 0.7824 0.240 Uiso 0.561(17) 1 calc PR A 2 C15 C -0.1228(3) 0.3351(2) 0.84390(13) 0.0609(7) Uani 1 1 d . . . C16 C 0.0860(3) 0.27809(19) 0.85396(13) 0.0587(7) Uani 1 1 d . . . C17 C 0.2152(3) 0.2563(3) 0.85903(18) 0.0831(9) Uani 0.29(2) 1 d P A 3 C18 C 0.2917(16) 0.3455(17) 0.862(3) 0.22(3) Uani 0.29(2) 1 d P A 3 H18A H 0.2856 0.3737 0.9043 0.335 Uiso 0.29(2) 1 calc PR A 3 H18B H 0.2641 0.3876 0.8282 0.335 Uiso 0.29(2) 1 calc PR A 3 H18C H 0.3725 0.3300 0.8539 0.335 Uiso 0.29(2) 1 calc PR A 3 C19 C 0.256(2) 0.204(3) 0.7983(11) 0.18(2) Uani 0.29(2) 1 d P A 3 H19A H 0.3391 0.1918 0.8029 0.268 Uiso 0.29(2) 1 calc PR A 3 H19B H 0.2420 0.2413 0.7596 0.268 Uiso 0.29(2) 1 calc PR A 3 H19C H 0.2137 0.1476 0.7942 0.268 Uiso 0.29(2) 1 calc PR A 3 C20 C 0.2412(15) 0.196(2) 0.9165(11) 0.126(12) Uani 0.29(2) 1 d P A 3 H20A H 0.1930 0.2138 0.9527 0.189 Uiso 0.29(2) 1 calc PR A 3 H20B H 0.3229 0.2018 0.9293 0.189 Uiso 0.29(2) 1 calc PR A 3 H20C H 0.2247 0.1332 0.9047 0.189 Uiso 0.29(2) 1 calc PR A 3 C17' C 0.2152(3) 0.2563(3) 0.85903(18) 0.0831(9) Uani 0.71(2) 1 d P A 4 C18' C 0.2660(6) 0.2974(11) 0.9215(4) 0.151(7) Uani 0.71(2) 1 d P A 4 H18D H 0.3487 0.2840 0.9247 0.226 Uiso 0.71(2) 1 calc PR A 4 H18E H 0.2271 0.2717 0.9589 0.226 Uiso 0.71(2) 1 calc PR A 4 H18F H 0.2546 0.3629 0.9208 0.226 Uiso 0.71(2) 1 calc PR A 4 C19' C 0.2704(8) 0.3021(12) 0.8021(5) 0.162(6) Uani 0.71(2) 1 d P A 4 H19D H 0.3538 0.2910 0.8036 0.242 Uiso 0.71(2) 1 calc PR A 4 H19E H 0.2559 0.3671 0.8041 0.242 Uiso 0.71(2) 1 calc PR A 4 H19F H 0.2373 0.2778 0.7617 0.242 Uiso 0.71(2) 1 calc PR A 4 C20' C 0.2335(9) 0.1517(6) 0.8599(12) 0.238(12) Uani 0.71(2) 1 d P A 4 H20D H 0.3163 0.1384 0.8632 0.357 Uiso 0.71(2) 1 calc PR A 4 H20E H 0.2014 0.1256 0.8198 0.357 Uiso 0.71(2) 1 calc PR A 4 H20F H 0.1944 0.1258 0.8971 0.357 Uiso 0.71(2) 1 calc PR A 4 O1 O 0.322(3) 0.535(3) 0.6721(15) 0.121(9) Uani 0.287(16) 1 d P B 5 C21 C 0.427(3) 0.511(4) 0.6789(15) 0.19(2) Uani 0.287(16) 1 d PD B 5 H21A H 0.4349 0.4590 0.7088 0.228 Uiso 0.287(16) 1 calc PR B 5 H21B H 0.4753 0.5613 0.6950 0.228 Uiso 0.287(16) 1 calc PR B 5 C22 C 0.457(3) 0.485(2) 0.6102(15) 0.20(2) Uani 0.287(16) 1 d PD B 5 H22A H 0.5246 0.5205 0.5972 0.244 Uiso 0.287(16) 1 calc PR B 5 H22B H 0.4792 0.4205 0.6099 0.244 Uiso 0.287(16) 1 calc PR B 5 C23 C 0.362(3) 0.499(2) 0.5604(11) 0.147(9) Uani 0.287(16) 1 d PDU B 5 H23A H 0.3894 0.5283 0.5206 0.177 Uiso 0.287(16) 1 calc PR B 5 H23B H 0.3208 0.4420 0.5492 0.177 Uiso 0.287(16) 1 calc PR B 5 C24 C 0.2958(5) 0.5569(5) 0.5991(3) 0.1458(19) Uani 0.287(16) 1 d P B 5 H24A H 0.2126 0.5486 0.5890 0.175 Uiso 0.287(16) 1 calc PR B 5 H24B H 0.3161 0.6205 0.5901 0.175 Uiso 0.287(16) 1 calc PR B 5 O1' O 0.2838(11) 0.5207(7) 0.6608(5) 0.092(2) Uani 0.713(16) 1 d P B 6 C21' C 0.3867(13) 0.4665(9) 0.6745(7) 0.143(5) Uani 0.713(16) 1 d PD B 6 H21C H 0.3722 0.4030 0.6620 0.171 Uiso 0.713(16) 1 calc PR B 6 H21D H 0.4059 0.4683 0.7214 0.171 Uiso 0.713(16) 1 calc PR B 6 C22' C 0.4859(11) 0.5038(15) 0.6366(10) 0.217(8) Uani 0.713(16) 1 d PD B 6 H22C H 0.5370 0.5419 0.6643 0.260 Uiso 0.713(16) 1 calc PR B 6 H22D H 0.5320 0.4548 0.6175 0.260 Uiso 0.713(16) 1 calc PR B 6 C23' C 0.4256(9) 0.5585(11) 0.5853(6) 0.169(6) Uani 0.713(16) 1 d PD B 6 H23C H 0.4399 0.5326 0.5420 0.202 Uiso 0.713(16) 1 calc PR B 6 H23D H 0.4547 0.6213 0.5861 0.202 Uiso 0.713(16) 1 calc PR B 6 C24' C 0.2958(5) 0.5569(5) 0.5991(3) 0.1458(19) Uani 0.713(16) 1 d P B 6 H24C H 0.2637 0.6188 0.5973 0.175 Uiso 0.713(16) 1 calc PR B 6 H24D H 0.2541 0.5194 0.5665 0.175 Uiso 0.713(16) 1 calc PR B 6 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 K1 0.0846(5) 0.0522(4) 0.0535(3) 0.0047(3) 0.0060(3) 0.0025(3) K2 0.1220(6) 0.0597(4) 0.0535(4) -0.0054(3) 0.0197(4) -0.0168(4) P1 0.1017(8) 0.0888(7) 0.0867(6) -0.0300(5) -0.0094(5) 0.0009(5) P2 0.0748(5) 0.0458(4) 0.0478(4) -0.0049(3) 0.0088(3) -0.0010(3) N1 0.0720(18) 0.0600(14) 0.0597(14) -0.0005(11) 0.0072(12) 0.0044(12) N2 0.0680(17) 0.0620(15) 0.0665(15) -0.0050(12) 0.0076(12) 0.0018(12) N3 0.0629(16) 0.0641(16) 0.0777(16) -0.0154(13) 0.0038(12) -0.0002(12) N4 0.0674(17) 0.0564(14) 0.0821(17) -0.0153(12) 0.0030(13) 0.0061(12) O2 0.1096(17) 0.0565(11) 0.0600(12) 0.0030(9) 0.0123(11) -0.0116(11) O3 0.1130(18) 0.0581(12) 0.0516(11) -0.0121(9) 0.0131(11) -0.0065(11) C1 0.105(3) 0.085(2) 0.079(2) 0.0025(19) 0.019(2) 0.034(2) C2 0.137(11) 0.155(11) 0.148(11) 0.088(10) 0.053(9) 0.081(9) C3 0.173(10) 0.161(13) 0.128(10) -0.075(10) -0.011(8) 0.079(9) C4 0.076(5) 0.126(6) 0.138(8) 0.001(5) 0.022(5) 0.022(4) C1' 0.105(3) 0.085(2) 0.079(2) 0.0025(19) 0.019(2) 0.034(2) C2' 0.20(2) 0.065(8) 0.23(2) 0.018(11) 0.065(17) 0.053(10) C3' 0.23(3) 0.20(3) 0.22(3) 0.10(2) 0.15(3) 0.16(3) C4' 0.12(2) 0.51(7) 0.16(3) -0.16(4) -0.051(19) 0.15(3) C5 0.088(2) 0.0581(17) 0.0566(16) 0.0007(14) 0.0091(15) 0.0087(15) C6 0.070(2) 0.074(2) 0.0642(18) 0.0029(15) 0.0055(15) -0.0002(16) C7 0.070(3) 0.128(3) 0.100(3) 0.003(2) 0.003(2) 0.013(2) C8 0.123(5) 0.149(5) 0.309(8) 0.079(5) 0.040(5) 0.070(4) C9 0.100(4) 0.279(8) 0.133(4) 0.031(4) 0.042(3) 0.054(4) C10 0.093(4) 0.361(11) 0.187(6) -0.083(6) -0.055(4) 0.051(5) C11 0.077(2) 0.097(3) 0.079(2) 0.001(2) 0.0089(18) 0.028(2) C12 0.097(10) 0.219(18) 0.076(8) 0.031(10) 0.027(7) 0.062(11) C13 0.102(11) 0.19(2) 0.172(15) -0.052(17) -0.032(12) 0.045(12) C14 0.168(15) 0.098(12) 0.20(2) 0.077(13) 0.052(13) 0.064(11) C11' 0.077(2) 0.097(3) 0.079(2) 0.001(2) 0.0089(18) 0.028(2) C12' 0.097(9) 0.266(17) 0.218(12) -0.140(11) -0.016(7) 0.106(11) C13' 0.053(5) 0.192(11) 0.23(2) 0.026(16) -0.012(9) -0.001(6) C14' 0.103(9) 0.18(2) 0.194(16) 0.091(16) 0.010(9) 0.072(13) C15 0.0663(19) 0.0591(17) 0.0577(16) -0.0037(13) 0.0101(13) 0.0074(14) C16 0.0620(19) 0.0601(17) 0.0542(15) -0.0068(13) 0.0047(13) 0.0029(14) C17 0.065(2) 0.095(3) 0.089(2) -0.009(2) 0.0017(18) 0.0123(18) C18 0.046(10) 0.15(2) 0.47(9) 0.11(3) -0.02(2) -0.016(11) C19 0.115(17) 0.32(5) 0.102(13) -0.07(2) -0.001(12) 0.14(3) C20 0.069(10) 0.17(3) 0.136(16) 0.056(16) -0.020(10) 0.015(13) C17' 0.065(2) 0.095(3) 0.089(2) -0.009(2) 0.0017(18) 0.0123(18) C18' 0.073(5) 0.26(2) 0.116(6) -0.030(8) -0.030(4) 0.013(7) C19' 0.068(5) 0.307(19) 0.112(6) 0.023(9) 0.028(4) 0.021(8) C20' 0.126(8) 0.108(7) 0.48(4) -0.053(12) -0.080(14) 0.062(6) O1 0.09(2) 0.193(19) 0.085(9) -0.042(10) 0.010(10) -0.017(12) C21 0.13(3) 0.24(5) 0.20(3) -0.04(4) -0.10(3) 0.04(3) C22 0.16(3) 0.22(4) 0.24(4) 0.07(3) 0.11(3) 0.14(3) C23 0.136(12) 0.163(12) 0.143(12) 0.000(9) 0.027(9) -0.003(9) C24 0.142(5) 0.188(6) 0.109(4) 0.011(4) 0.036(3) 0.008(4) O1' 0.078(6) 0.106(4) 0.091(5) 0.007(4) 0.020(4) 0.004(3) C21' 0.124(11) 0.132(9) 0.174(12) 0.039(7) 0.048(9) 0.028(7) C22' 0.109(9) 0.217(16) 0.33(2) 0.024(16) 0.066(11) -0.034(10) C23' 0.109(8) 0.247(13) 0.152(8) 0.060(9) 0.048(6) 0.010(8) C24' 0.142(5) 0.188(6) 0.109(4) 0.011(4) 0.036(3) 0.008(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 K1 O2 2.637(2) . ? K1 N2 2.735(3) . ? K1 N1 2.792(2) . ? K1 N3 2.802(3) 2_556 ? K1 N4 2.881(3) 2_556 ? K1 K2 4.0355(16) . ? K2 O3 2.601(2) 3_567 ? K2 O3 2.778(2) . ? K2 N1 2.794(2) . ? K2 O2 2.876(2) . ? K2 N2 2.889(3) . ? K2 C5 3.129(3) . ? K2 C6 3.280(3) . ? K2 P2 3.3067(13) . ? K2 P1 3.6310(16) . ? K2 K2 4.0380(15) 3_567 ? P1 C5 1.738(3) . ? P1 C6 1.743(3) . ? P2 O2 1.474(2) . ? P2 O3 1.4879(19) . ? P2 C15 1.824(3) . ? P2 C16 1.829(3) . ? N1 C5 1.319(3) . ? N1 N2 1.369(3) . ? N2 C6 1.315(4) . ? N3 C15 1.261(3) . ? N3 N4 1.491(3) . ? N3 K1 2.802(3) 2_546 ? N4 C16 1.264(3) . ? N4 K1 2.881(3) 2_546 ? O3 K2 2.601(2) 3_567 ? C1 C2 1.456(9) . ? C1 C3 1.499(11) . ? C1 C5 1.519(5) . ? C1 C4 1.609(9) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C2' H2'1 0.9600 . ? C2' H2'2 0.9600 . ? C2' H2'3 0.9600 . ? C3' H3'1 0.9600 . ? C3' H3'2 0.9600 . ? C3' H3'3 0.9600 . ? C4' H4'1 0.9600 . ? C4' H4'2 0.9600 . ? C4' H4'3 0.9600 . ? C6 C7 1.514(5) . ? C7 C9 1.485(6) . ? C7 C8 1.510(7) . ? C7 C10 1.534(5) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.4397 . ? C11 C15 1.503(4) . ? C11 C14 1.62(2) . ? C11 C13 1.622(19) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C12' H12A 1.4074 . ? C12' H12B 0.5930 . ? C12' H12D 0.9600 . ? C12' H12E 0.9600 . ? C12' H12F 0.9600 . ? C13' H13D 0.9600 . ? C13' H13E 0.9600 . ? C13' H13F 0.9600 . ? C14' H14D 0.9600 . ? C14' H14E 0.9600 . ? C14' H14F 0.9600 . ? C16 C17 1.501(4) . ? C17 C20 1.481(16) . ? C17 C19 1.523(17) . ? C17 C18 1.56(2) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C18' H18D 0.9600 . ? C18' H18E 0.9600 . ? C18' H18F 0.9600 . ? C19' H19D 0.9600 . ? C19' H19E 0.9600 . ? C19' H19F 0.9600 . ? C20' H20D 0.9600 . ? C20' H20E 0.9600 . ? C20' H20F 0.9600 . ? O1 C21 1.25(6) . ? O1 C24 1.53(3) . ? C21 C22 1.488(10) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.470(10) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.39(2) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? O1' C21' 1.43(2) . ? C21' C22' 1.479(9) . ? C21' H21C 0.9700 . ? C21' H21D 0.9700 . ? C22' C23' 1.465(9) . ? C22' H22C 0.9700 . ? C22' H22D 0.9700 . ? C23' H23C 0.9700 . ? C23' H23D 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 K1 N2 87.41(7) . . ? O2 K1 N1 88.41(7) . . ? N2 K1 N1 28.66(7) . . ? O2 K1 N3 157.01(8) . 2_556 ? N2 K1 N3 90.73(8) . 2_556 ? N1 K1 N3 79.25(7) . 2_556 ? O2 K1 N4 131.31(8) . 2_556 ? N2 K1 N4 110.57(8) . 2_556 ? N1 K1 N4 88.58(8) . 2_556 ? N3 K1 N4 30.37(7) 2_556 2_556 ? O2 K1 K2 45.31(4) . . ? N2 K1 K2 45.69(5) . . ? N1 K1 K2 43.76(5) . . ? N3 K1 K2 122.20(6) 2_556 . ? N4 K1 K2 120.87(6) 2_556 . ? O3 K2 O3 82.76(6) 3_567 . ? O3 K2 N1 128.46(7) 3_567 . ? O3 K2 N1 135.79(7) . . ? O3 K2 O2 129.62(7) 3_567 . ? O3 K2 O2 52.96(5) . . ? N1 K2 O2 83.80(7) . . ? O3 K2 N2 147.01(7) 3_567 . ? O3 K2 N2 130.17(6) . . ? N1 K2 N2 27.82(7) . . ? O2 K2 N2 80.17(7) . . ? O3 K2 C5 106.20(7) 3_567 . ? O3 K2 C5 156.73(8) . . ? N1 K2 C5 24.92(7) . . ? O2 K2 C5 108.11(7) . . ? N2 K2 C5 43.24(7) . . ? O3 K2 C6 129.16(7) 3_567 . ? O3 K2 C6 143.14(7) . . ? N1 K2 C6 42.34(7) . . ? O2 K2 C6 101.02(7) . . ? N2 K2 C6 23.54(7) . . ? C5 K2 C6 43.49(8) . . ? O3 K2 P2 106.81(5) 3_567 . ? O3 K2 P2 26.53(4) . . ? N1 K2 P2 109.90(6) . . ? O2 K2 P2 26.43(4) . . ? N2 K2 P2 105.21(5) . . ? C5 K2 P2 133.46(6) . . ? C6 K2 P2 123.38(6) . . ? O3 K2 P1 102.97(5) 3_567 . ? O3 K2 P1 170.73(6) . . ? N1 K2 P1 45.13(5) . . ? O2 K2 P1 124.43(5) . . ? N2 K2 P1 44.76(5) . . ? C5 K2 P1 28.58(6) . . ? C6 K2 P1 28.63(6) . . ? P2 K2 P1 149.97(3) . . ? O3 K2 K1 153.39(6) 3_567 . ? O3 K2 K1 93.63(4) . . ? N1 K2 K1 43.73(5) . . ? O2 K2 K1 40.68(4) . . ? N2 K2 K1 42.64(5) . . ? C5 K2 K1 68.59(5) . . ? C6 K2 K1 65.95(6) . . ? P2 K2 K1 67.11(2) . . ? P1 K2 K1 84.46(2) . . ? O3 K2 K2 43.04(4) 3_567 3_567 ? O3 K2 K2 39.73(4) . 3_567 ? N1 K2 K2 153.36(7) . 3_567 ? O2 K2 K2 89.80(5) . 3_567 ? N2 K2 K2 169.78(6) . 3_567 ? C5 K2 K2 144.26(7) . 3_567 ? C6 K2 K2 163.18(6) . 3_567 ? P2 K2 K2 64.59(3) . 3_567 ? P1 K2 K2 145.44(3) . 3_567 ? K1 K2 K2 128.28(3) . 3_567 ? C5 P1 C6 86.21(15) . . ? C5 P1 K2 59.45(10) . . ? C6 P1 K2 64.43(11) . . ? O2 P2 O3 116.73(11) . . ? O2 P2 C15 113.77(13) . . ? O3 P2 C15 110.94(13) . . ? O2 P2 C16 112.79(13) . . ? O3 P2 C16 111.90(12) . . ? C15 P2 C16 87.03(13) . . ? O2 P2 K2 60.25(8) . . ? O3 P2 K2 56.50(8) . . ? C15 P2 K2 137.54(9) . . ? C16 P2 K2 135.24(10) . . ? C5 N1 N2 112.0(2) . . ? C5 N1 K1 173.7(2) . . ? N2 N1 K1 73.34(14) . . ? C5 N1 K2 91.89(17) . . ? N2 N1 K2 79.96(14) . . ? K1 N1 K2 92.51(8) . . ? C6 N2 N1 113.1(2) . . ? C6 N2 K1 168.4(2) . . ? N1 N2 K1 77.99(15) . . ? C6 N2 K2 95.14(18) . . ? N1 N2 K2 72.23(14) . . ? K1 N2 K2 91.67(8) . . ? C15 N3 N4 113.8(2) . . ? C15 N3 K1 162.1(2) . 2_546 ? N4 N3 K1 77.78(13) . 2_546 ? C16 N4 N3 114.1(2) . . ? C16 N4 K1 166.3(2) . 2_546 ? N3 N4 K1 71.85(13) . 2_546 ? P2 O2 K1 172.66(12) . . ? P2 O2 K2 93.32(9) . . ? K1 O2 K2 94.02(7) . . ? P2 O3 K2 151.41(14) . 3_567 ? P2 O3 K2 96.98(9) . . ? K2 O3 K2 97.24(6) 3_567 . ? C2 C1 C3 116.4(8) . . ? C2 C1 C5 109.6(5) . . ? C3 C1 C5 112.4(6) . . ? C2 C1 C4 106.9(7) . . ? C3 C1 C4 101.9(7) . . ? C5 C1 C4 109.0(4) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? H2'1 C2' H2'2 109.5 . . ? H2'1 C2' H2'3 109.5 . . ? H2'2 C2' H2'3 109.5 . . ? H3'1 C3' H3'2 109.5 . . ? H3'1 C3' H3'3 109.5 . . ? H3'2 C3' H3'3 109.5 . . ? H4'1 C4' H4'2 109.5 . . ? H4'1 C4' H4'3 109.5 . . ? H4'2 C4' H4'3 109.5 . . ? N1 C5 C1 117.8(3) . . ? N1 C5 P1 114.7(2) . . ? C1 C5 P1 127.5(2) . . ? N1 C5 K2 63.19(15) . . ? C1 C5 K2 110.0(2) . . ? P1 C5 K2 91.97(11) . . ? N2 C6 C7 117.5(3) . . ? N2 C6 P1 114.0(2) . . ? C7 C6 P1 128.5(3) . . ? N2 C6 K2 61.32(16) . . ? C7 C6 K2 116.8(2) . . ? P1 C6 K2 86.94(12) . . ? C9 C7 C8 112.4(5) . . ? C9 C7 C6 110.6(3) . . ? C8 C7 C6 108.6(4) . . ? C9 C7 C10 109.6(4) . . ? C8 C7 C10 106.4(4) . . ? C6 C7 C10 109.2(3) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C15 112.60(15) . . ? C12 C11 C14 112.0(10) . . ? C15 C11 C14 111.1(10) . . ? C12 C11 C13 108.7(9) . . ? C15 C11 C13 110.6(7) . . ? C14 C11 C13 101.4(14) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? H12A C12' H12B 94.3 . . ? H12A C12' H12D 83.5 . . ? H12B C12' H12D 17.5 . . ? H12A C12' H12E 47.2 . . ? H12B C12' H12E 107.8 . . ? H12D C12' H12E 109.5 . . ? H12A C12' H12F 156.7 . . ? H12B C12' H12F 94.5 . . ? H12D C12' H12F 109.5 . . ? H12E C12' H12F 109.5 . . ? H13D C13' H13E 109.5 . . ? H13D C13' H13F 109.5 . . ? H13E C13' H13F 109.5 . . ? H14D C14' H14E 109.5 . . ? H14D C14' H14F 109.5 . . ? H14E C14' H14F 109.5 . . ? N3 C15 C11 120.7(3) . . ? N3 C15 P2 112.7(2) . . ? C11 C15 P2 126.6(2) . . ? N4 C16 C17 120.5(3) . . ? N4 C16 P2 112.3(2) . . ? C17 C16 P2 127.2(2) . . ? C20 C17 C16 110.8(7) . . ? C20 C17 C19 106.3(14) . . ? C16 C17 C19 111.4(8) . . ? C20 C17 C18 111.4(17) . . ? C16 C17 C18 111.7(8) . . ? C19 C17 C18 105(2) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? H18D C18' H18E 109.5 . . ? H18D C18' H18F 109.5 . . ? H18E C18' H18F 109.5 . . ? H19D C19' H19E 109.5 . . ? H19D C19' H19F 109.5 . . ? H19E C19' H19F 109.5 . . ? H20D C20' H20E 109.5 . . ? H20D C20' H20F 109.5 . . ? H20E C20' H20F 109.5 . . ? C21 O1 C24 109(3) . . ? O1 C21 C22 102(2) . . ? O1 C21 H21A 111.4 . . ? C22 C21 H21A 111.4 . . ? O1 C21 H21B 111.4 . . ? C22 C21 H21B 111.4 . . ? H21A C21 H21B 109.3 . . ? C23 C22 C21 115(2) . . ? C23 C22 H22A 108.4 . . ? C21 C22 H22A 108.4 . . ? C23 C22 H22B 108.4 . . ? C21 C22 H22B 108.4 . . ? H22A C22 H22B 107.5 . . ? C24 C23 C22 95.3(16) . . ? C24 C23 H23A 112.7 . . ? C22 C23 H23A 112.7 . . ? C24 C23 H23B 112.7 . . ? C22 C23 H23B 112.7 . . ? H23A C23 H23B 110.2 . . ? C23 C24 O1 108.8(19) . . ? C23 C24 H24A 109.9 . . ? O1 C24 H24A 109.9 . . ? C23 C24 H24B 109.9 . . ? O1 C24 H24B 109.9 . . ? H24A C24 H24B 108.3 . . ? O1' C21' C22' 109.0(11) . . ? O1' C21' H21C 109.9 . . ? C22' C21' H21C 109.9 . . ? O1' C21' H21D 109.9 . . ? C22' C21' H21D 109.9 . . ? H21C C21' H21D 108.3 . . ? C23' C22' C21' 102.5(11) . . ? C23' C22' H22C 111.3 . . ? C21' C22' H22C 111.3 . . ? C23' C22' H22D 111.3 . . ? C21' C22' H22D 111.3 . . ? H22C C22' H22D 109.2 . . ? C22' C23' H23C 110.2 . . ? C22' C23' H23D 110.2 . . ? H23C C23' H23D 108.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.312 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.051