Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 186 loop_ _publ_author_name 'H. Schmidbaur' 'Frank. Wiesbrock' _publ_contact_author_name 'Prof H Schmidbaur' _publ_contact_author_address ; Lehrstuhl fur Anorganische und Anal Technischen Universitat Munchen Lichtenbergstrase 4 Garching D-85747 GERMANY ; _publ_contact_author_email 'H.SCHMIDBAUR@LRZ.TUM.DE' _publ_requested_journal 'Dalton Transactions' _publ_section_title ; The structural Chemistry of Lithium, Sodium and Potassium Anthranilate Hydrates ; data_wies8 _database_code_CSD 193293 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H7 N Na O2.50' _chemical_formula_weight 168.13 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' 'Na' 'Na' 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M Pc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 15.4990(3) _cell_length_b 5.7220(1) _cell_length_c 8.1530(1) _cell_angle_alpha 90.00 _cell_angle_beta 104.340(1) _cell_angle_gamma 90.00 _cell_volume 700.52(2) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 17617 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.594 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.172 _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 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17617 _diffrn_reflns_av_R_equivalents 0.0031 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 27.16 _reflns_number_total 2866 _reflns_number_gt 2858 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; The structure was refined as racemic twin. 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^)+(0.0672P)^2^+0.0341P] 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 0.067(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.42(17) _refine_ls_number_reflns 2866 _refine_ls_number_parameters 266 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0313 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0815 _refine_ls_wR_factor_gt 0.0814 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.064 _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 Na1 Na -0.42548(4) -0.10496(9) -0.34385(7) 0.01886(15) Uani 1 1 d . . . Na2 Na -0.30531(4) -0.35206(10) 0.06472(7) 0.02115(15) Uani 1 1 d . . . O12 O -0.28465(7) -0.30009(16) -0.25070(14) 0.0209(2) Uani 1 1 d . . . O22 O -0.44994(6) -0.20521(17) -0.06464(13) 0.0195(2) Uani 1 1 d . . . N1 N -0.16127(8) -0.5485(2) -0.03184(17) 0.0222(3) Uani 1 1 d . . . C12 C -0.10240(9) -0.3814(2) -0.06422(17) 0.0183(3) Uani 1 1 d . . . C22 C -0.63508(9) -0.1353(2) -0.24080(17) 0.0174(3) Uani 1 1 d . . . O11 O -0.24075(7) -0.00894(17) -0.39197(13) 0.0213(2) Uani 1 1 d . . . C21 C -0.60126(8) -0.3339(2) -0.14168(17) 0.0165(3) Uani 1 1 d . . . C11 C -0.13060(8) -0.1903(2) -0.17376(18) 0.0166(3) Uani 1 1 d . . . C26 C -0.66129(9) -0.4983(2) -0.10673(19) 0.0209(3) Uani 1 1 d . . . C23 C -0.72752(10) -0.1133(3) -0.3034(2) 0.0238(3) Uani 1 1 d . . . C13 C -0.01160(9) -0.4007(2) 0.02060(19) 0.0239(3) Uani 1 1 d . . . C24 C -0.78556(10) -0.2766(3) -0.2660(2) 0.0275(3) Uani 1 1 d . . . C17 C -0.22463(9) -0.1637(2) -0.27732(17) 0.0164(3) Uani 1 1 d . . . C16 C -0.06682(10) -0.0252(2) -0.19475(19) 0.0215(3) Uani 1 1 d . . . C25 C -0.75288(10) -0.4713(3) -0.1662(2) 0.0269(3) Uani 1 1 d . . . C15 C 0.02216(10) -0.0453(3) -0.1104(2) 0.0259(3) Uani 1 1 d . . . C14 C 0.04939(10) -0.2354(3) -0.0030(2) 0.0272(3) Uani 1 1 d . . . O21 O -0.47714(7) -0.58113(17) -0.02699(14) 0.0237(2) Uani 1 1 d . . . C27 C -0.50312(9) -0.3748(2) -0.07268(17) 0.0168(3) Uani 1 1 d . . . N2 N -0.57955(8) 0.0334(2) -0.28610(18) 0.0209(2) Uani 1 1 d . . . O01 O -0.35095(8) 0.21787(17) -0.17580(14) 0.0212(2) Uani 1 1 d . . . H16 H -0.0876(15) 0.108(4) -0.273(3) 0.027(5) Uiso 1 1 d . . . H04 H -0.2108(15) -0.568(4) -0.120(3) 0.023(5) Uiso 1 1 d . . . H14 H 0.1179(17) -0.260(4) 0.065(3) 0.036(6) Uiso 1 1 d . . . H15 H 0.0670(18) 0.079(4) -0.126(4) 0.037(6) Uiso 1 1 d . . . H13 H 0.0071(18) -0.539(4) 0.102(3) 0.036(6) Uiso 1 1 d . . . H02 H -0.319(2) 0.145(5) -0.100(5) 0.055(8) Uiso 1 1 d . . . H23 H -0.7538(18) 0.023(4) -0.379(4) 0.041(6) Uiso 1 1 d . . . H24 H -0.8477(16) -0.246(4) -0.312(3) 0.032(5) Uiso 1 1 d . . . H06 H -0.5361(18) 0.076(4) -0.196(3) 0.035(6) Uiso 1 1 d . . . H03 H -0.1416(18) -0.676(5) 0.005(4) 0.042(7) Uiso 1 1 d . . . H01 H -0.3882(18) 0.291(5) -0.141(4) 0.039(6) Uiso 1 1 d . . . H25 H -0.7974(17) -0.583(4) -0.138(3) 0.033(6) Uiso 1 1 d . . . H05 H -0.6102(16) 0.144(4) -0.342(3) 0.032(5) Uiso 1 1 d . . . H26 H -0.6363(16) -0.627(4) -0.032(3) 0.032(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Na1 0.0187(3) 0.0174(2) 0.0195(3) -0.00075(18) 0.0029(2) -0.00012(19) Na2 0.0199(3) 0.0170(2) 0.0248(3) 0.0000(2) 0.0024(2) 0.0003(2) O12 0.0161(5) 0.0195(4) 0.0261(5) 0.0005(3) 0.0037(4) -0.0010(3) O22 0.0148(4) 0.0217(4) 0.0211(5) 0.0000(4) 0.0025(4) -0.0020(3) N1 0.0221(6) 0.0197(6) 0.0235(7) 0.0062(5) 0.0036(5) -0.0004(4) C12 0.0173(6) 0.0202(6) 0.0168(7) -0.0003(5) 0.0030(5) 0.0011(4) C22 0.0183(7) 0.0170(6) 0.0165(7) -0.0020(4) 0.0034(5) 0.0013(4) O11 0.0234(5) 0.0185(4) 0.0203(5) 0.0035(3) 0.0021(4) 0.0021(4) C21 0.0161(6) 0.0173(6) 0.0157(7) 0.0000(5) 0.0032(5) 0.0008(4) C11 0.0154(6) 0.0170(6) 0.0177(7) -0.0009(4) 0.0044(5) -0.0010(4) C26 0.0219(7) 0.0208(6) 0.0207(7) 0.0000(4) 0.0065(5) -0.0024(5) C23 0.0199(7) 0.0251(7) 0.0248(8) -0.0006(5) 0.0024(6) 0.0042(5) C13 0.0171(7) 0.0276(7) 0.0251(8) 0.0013(5) 0.0014(5) 0.0040(5) C24 0.0169(6) 0.0340(8) 0.0305(8) -0.0038(6) 0.0039(5) 0.0001(5) C17 0.0160(6) 0.0156(5) 0.0171(7) -0.0023(4) 0.0033(5) 0.0015(4) C16 0.0205(7) 0.0212(6) 0.0228(7) -0.0004(5) 0.0057(5) -0.0040(5) C25 0.0209(7) 0.0295(7) 0.0309(8) -0.0017(6) 0.0077(6) -0.0068(6) C15 0.0195(7) 0.0297(7) 0.0284(8) -0.0013(6) 0.0059(6) -0.0069(5) C14 0.0159(6) 0.0357(8) 0.0276(8) -0.0020(6) 0.0007(5) 0.0001(5) O21 0.0231(5) 0.0196(4) 0.0271(6) 0.0056(4) 0.0037(4) 0.0050(4) C27 0.0183(6) 0.0173(6) 0.0151(6) 0.0008(4) 0.0049(5) 0.0014(4) N2 0.0204(5) 0.0174(5) 0.0235(6) 0.0030(5) 0.0028(5) 0.0013(4) O01 0.0210(4) 0.0205(5) 0.0214(5) 0.0010(4) 0.0041(4) 0.0004(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 Na1 O21 2.3462(11) 2_544 ? Na1 O12 2.4013(11) . ? Na1 O01 2.4165(11) . ? Na1 O22 2.4663(12) . ? Na1 O22 2.4892(11) 2_554 ? Na1 N2 2.6660(14) . ? Na1 C17 3.0432(14) . ? Na1 Na2 3.3986(8) 2_554 ? Na1 Na2 3.6730(7) . ? Na1 Na2 3.7901(8) 2_544 ? Na1 H02 2.66(3) . ? Na1 H06 2.55(3) . ? Na2 O11 2.2843(11) 2 ? Na2 O22 2.3817(11) . ? Na2 O12 2.4678(12) 2_545 ? Na2 O01 2.5113(13) 2 ? Na2 O12 2.6856(13) . ? Na2 N1 2.7818(14) . ? Na2 O21 2.8954(12) . ? Na2 C27 2.9950(15) . ? Na2 Na1 3.3986(8) 2 ? Na2 Na1 3.7901(8) 2_545 ? Na2 H04 2.65(2) . ? O12 C17 1.2735(17) . ? O12 Na2 2.4678(12) 2_544 ? O22 C27 1.2645(17) . ? O22 Na1 2.4892(11) 2 ? N1 C12 1.3913(18) . ? N1 H04 0.92(2) . ? N1 H03 0.82(3) . ? C12 C13 1.410(2) . ? C12 C11 1.4110(17) . ? C22 N2 1.4024(17) . ? C22 C23 1.403(2) . ? C22 C21 1.4173(17) . ? O11 C17 1.2666(18) . ? O11 Na2 2.2843(11) 2_554 ? C21 C26 1.4013(18) . ? C21 C27 1.5037(18) . ? C11 C16 1.4084(18) . ? C11 C17 1.5001(18) . ? C26 C25 1.391(2) . ? C26 H26 0.97(3) . ? C23 C24 1.382(2) . ? C23 H23 1.01(3) . ? C13 C14 1.384(2) . ? C13 H13 1.02(3) . ? C24 C25 1.398(2) . ? C24 H24 0.96(2) . ? C16 C15 1.385(2) . ? C16 H16 0.99(2) . ? C25 H25 1.01(2) . ? C15 C14 1.395(2) . ? C15 H15 1.03(3) . ? C14 H14 1.08(3) . ? O21 C27 1.2727(16) . ? O21 Na1 2.3462(11) 2_545 ? N2 H06 0.90(3) . ? N2 H05 0.85(2) . ? O01 Na2 2.5113(13) 2_554 ? O01 H02 0.81(4) . ? O01 H01 0.82(3) . ? 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 O21 Na1 O12 89.17(4) 2_544 . ? O21 Na1 O01 170.37(4) 2_544 . ? O12 Na1 O01 84.65(4) . . ? O21 Na1 O22 107.64(4) 2_544 . ? O12 Na1 O22 86.30(4) . . ? O01 Na1 O22 79.38(4) . . ? O21 Na1 O22 96.82(4) 2_544 2_554 ? O12 Na1 O22 121.60(4) . 2_554 ? O01 Na1 O22 80.26(4) . 2_554 ? O22 Na1 O22 143.38(4) . 2_554 ? O21 Na1 N2 99.22(4) 2_544 . ? O12 Na1 N2 149.99(5) . . ? O01 Na1 N2 89.78(4) . . ? O22 Na1 N2 63.69(4) . . ? O22 Na1 N2 86.18(4) 2_554 . ? O21 Na1 C17 101.64(4) 2_544 . ? O12 Na1 C17 23.48(3) . . ? O01 Na1 C17 70.07(4) . . ? O22 Na1 C17 101.20(4) . . ? O22 Na1 C17 99.99(4) 2_554 . ? N2 Na1 C17 157.33(5) . . ? O21 Na1 Na2 124.66(3) 2_544 2_554 ? O12 Na1 Na2 85.56(3) . 2_554 ? O01 Na1 Na2 47.56(3) . 2_554 ? O22 Na1 Na2 126.82(3) . 2_554 ? O22 Na1 Na2 44.47(3) 2_554 2_554 ? N2 Na1 Na2 111.95(3) . 2_554 ? C17 Na1 Na2 62.10(3) . 2_554 ? O21 Na1 Na2 107.39(3) 2_544 . ? O12 Na1 Na2 46.94(3) . . ? O01 Na1 Na2 73.52(3) . . ? O22 Na1 Na2 39.89(3) . . ? O22 Na1 Na2 151.95(3) 2_554 . ? N2 Na1 Na2 103.26(4) . . ? C17 Na1 Na2 61.92(3) . . ? Na2 Na1 Na2 108.23(2) 2_554 . ? O21 Na1 Na2 49.77(3) 2_544 2_544 ? O12 Na1 Na2 39.52(3) . 2_544 ? O01 Na1 Na2 123.30(3) . 2_544 ? O22 Na1 Na2 100.73(3) . 2_544 ? O22 Na1 Na2 115.88(3) 2_554 2_544 ? N2 Na1 Na2 141.57(3) . 2_544 ? C17 Na1 Na2 54.11(3) . 2_544 ? Na2 Na1 Na2 105.36(2) 2_554 2_544 ? Na2 Na1 Na2 72.502(12) . 2_544 ? O21 Na1 H02 159.5(7) 2_544 . ? O12 Na1 H02 70.6(7) . . ? O01 Na1 H02 17.4(7) . . ? O22 Na1 H02 69.1(8) . . ? O22 Na1 H02 96.5(7) 2_554 . ? N2 Na1 H02 97.1(8) . . ? C17 Na1 H02 60.6(8) . . ? Na2 Na1 H02 58.6(8) 2_554 . ? Na2 Na1 H02 56.5(7) . . ? Na2 Na1 H02 110.1(7) 2_544 . ? O21 Na1 H06 116.7(6) 2_544 . ? O12 Na1 H06 134.8(6) . . ? O01 Na1 H06 72.8(6) . . ? O22 Na1 H06 51.9(6) . . ? O22 Na1 H06 93.0(6) 2_554 . ? N2 Na1 H06 19.7(6) . . ? C17 Na1 H06 137.6(6) . . ? Na2 Na1 H06 105.1(5) 2_554 . ? Na2 Na1 H06 88.7(6) . . ? Na2 Na1 H06 148.0(5) 2_544 . ? H02 Na1 H06 78.0(10) . . ? O11 Na2 O22 94.45(4) 2 . ? O11 Na2 O12 130.49(4) 2 2_545 ? O22 Na2 O12 121.36(4) . 2_545 ? O11 Na2 O01 78.30(4) 2 2 ? O22 Na2 O01 80.48(4) . 2 ? O12 Na2 O01 75.76(4) 2_545 2 ? O11 Na2 O12 84.05(4) 2 . ? O22 Na2 O12 81.91(4) . . ? O12 Na2 O12 130.17(4) 2_545 . ? O01 Na2 O12 153.91(4) 2 . ? O11 Na2 N1 93.31(4) 2 . ? O22 Na2 N1 138.64(5) . . ? O12 Na2 N1 81.64(4) 2_545 . ? O01 Na2 N1 140.82(4) 2 . ? O12 Na2 N1 58.63(4) . . ? O11 Na2 O21 142.09(4) 2 . ? O22 Na2 O21 48.75(3) . . ? O12 Na2 O21 76.38(3) 2_545 . ? O01 Na2 O21 85.58(4) 2 . ? O12 Na2 O21 97.07(4) . . ? N1 Na2 O21 119.69(4) . . ? O11 Na2 C27 117.76(4) 2 . ? O22 Na2 C27 23.90(3) . . ? O12 Na2 C27 99.16(4) 2_545 . ? O01 Na2 C27 81.52(4) 2 . ? O12 Na2 C27 90.03(4) . . ? N1 Na2 C27 134.07(4) . . ? O21 Na2 C27 24.88(3) . . ? O11 Na2 Na1 60.87(3) 2 2 ? O22 Na2 Na1 47.07(3) . 2 ? O12 Na2 Na1 118.83(3) 2_545 2 ? O01 Na2 Na1 45.25(3) 2 2 ? O12 Na2 Na1 109.06(3) . 2 ? N1 Na2 Na1 153.49(3) . 2 ? O21 Na2 Na1 83.46(3) . 2 ? C27 Na2 Na1 63.24(3) . 2 ? O11 Na2 Na1 84.05(3) 2 . ? O22 Na2 Na1 41.61(3) . . ? O12 Na2 Na1 145.45(3) 2_545 . ? O01 Na2 Na1 117.45(3) 2 . ? O12 Na2 Na1 40.79(2) . . ? N1 Na2 Na1 99.27(3) . . ? O21 Na2 Na1 73.30(3) . . ? C27 Na2 Na1 55.62(3) . . ? Na1 Na2 Na1 73.763(13) 2 . ? O11 Na2 Na1 158.23(4) 2 2_545 ? O22 Na2 Na1 85.52(3) . 2_545 ? O12 Na2 Na1 38.26(3) 2_545 2_545 ? O01 Na2 Na1 80.23(3) 2 2_545 ? O12 Na2 Na1 117.39(3) . 2_545 ? N1 Na2 Na1 101.09(3) . 2_545 ? O21 Na2 Na1 38.22(2) . 2_545 ? C27 Na2 Na1 62.00(3) . 2_545 ? Na1 Na2 Na1 105.36(2) 2 2_545 ? Na1 Na2 Na1 109.296(19) . 2_545 ? O11 Na2 H04 103.1(5) 2 . ? O22 Na2 H04 120.3(5) . . ? O12 Na2 H04 87.9(5) 2_545 . ? O01 Na2 H04 158.7(5) 2 . ? O12 Na2 H04 45.1(5) . . ? N1 Na2 H04 19.3(5) . . ? O21 Na2 H04 104.1(5) . . ? C27 Na2 H04 115.2(5) . . ? Na1 Na2 H04 153.2(5) 2 . ? Na1 Na2 H04 83.8(5) . . ? Na1 Na2 H04 95.6(4) 2_545 . ? C17 O12 Na1 107.83(8) . . ? C17 O12 Na2 112.36(9) . 2_544 ? Na1 O12 Na2 102.22(4) . 2_544 ? C17 O12 Na2 119.76(9) . . ? Na1 O12 Na2 92.27(4) . . ? Na2 O12 Na2 117.80(4) 2_544 . ? C27 O22 Na2 106.38(8) . . ? C27 O22 Na1 112.21(8) . . ? Na2 O22 Na1 98.50(4) . . ? C27 O22 Na1 124.43(9) . 2 ? Na2 O22 Na1 88.47(4) . 2 ? Na1 O22 Na1 118.10(4) . 2 ? C12 N1 Na2 112.70(9) . . ? C12 N1 H04 113.2(13) . . ? Na2 N1 H04 72.4(13) . . ? C12 N1 H03 118.8(19) . . ? Na2 N1 H03 120.4(19) . . ? H04 N1 H03 110(2) . . ? N1 C12 C13 118.35(12) . . ? N1 C12 C11 122.53(12) . . ? C13 C12 C11 119.08(12) . . ? N2 C22 C23 118.72(12) . . ? N2 C22 C21 122.52(12) . . ? C23 C22 C21 118.67(12) . . ? C17 O11 Na2 138.15(9) . 2_554 ? C26 C21 C22 118.94(12) . . ? C26 C21 C27 118.70(11) . . ? C22 C21 C27 122.36(11) . . ? C16 C11 C12 118.69(12) . . ? C16 C11 C17 118.46(12) . . ? C12 C11 C17 122.72(12) . . ? C25 C26 C21 121.74(13) . . ? C25 C26 H26 121.1(15) . . ? C21 C26 H26 117.0(15) . . ? C24 C23 C22 121.40(14) . . ? C24 C23 H23 117.9(15) . . ? C22 C23 H23 120.7(15) . . ? C14 C13 C12 120.77(14) . . ? C14 C13 H13 121.5(15) . . ? C12 C13 H13 117.7(15) . . ? C23 C24 C25 120.34(14) . . ? C23 C24 H24 115.9(14) . . ? C25 C24 H24 123.8(14) . . ? O11 C17 O12 122.36(12) . . ? O11 C17 C11 118.24(12) . . ? O12 C17 C11 119.37(12) . . ? O11 C17 Na1 77.59(8) . . ? O12 C17 Na1 48.69(6) . . ? C11 C17 Na1 156.90(9) . . ? C15 C16 C11 121.78(14) . . ? C15 C16 H16 120.5(13) . . ? C11 C16 H16 117.8(13) . . ? C26 C25 C24 118.89(13) . . ? C26 C25 H25 123.1(14) . . ? C24 C25 H25 118.0(14) . . ? C16 C15 C14 119.04(14) . . ? C16 C15 H15 120.2(15) . . ? C14 C15 H15 120.8(15) . . ? C13 C14 C15 120.63(13) . . ? C13 C14 H14 117.3(13) . . ? C15 C14 H14 122.1(13) . . ? C27 O21 Na1 158.38(10) . 2_545 ? C27 O21 Na2 81.94(8) . . ? Na1 O21 Na2 92.01(4) 2_545 . ? O22 C27 O21 122.81(13) . . ? O22 C27 C21 119.06(11) . . ? O21 C27 C21 118.13(12) . . ? O22 C27 Na2 49.72(7) . . ? O21 C27 Na2 73.18(8) . . ? C21 C27 Na2 168.54(9) . . ? C22 N2 Na1 118.49(8) . . ? C22 N2 H06 110.9(16) . . ? Na1 N2 H06 72.8(16) . . ? C22 N2 H05 110.7(16) . . ? Na1 N2 H05 122.0(16) . . ? H06 N2 H05 116(2) . . ? Na1 O01 Na2 87.19(4) . 2_554 ? Na1 O01 H02 99(2) . . ? Na2 O01 H02 124(3) 2_554 . ? Na1 O01 H01 107.9(18) . . ? Na2 O01 H01 120.2(19) 2_554 . ? H02 O01 H01 111(3) . . ? 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 O21 Na1 Na2 O11 159.50(4) 2_544 . . 2 ? O12 Na1 Na2 O11 87.77(5) . . . 2 ? O01 Na1 Na2 O11 -10.47(4) . . . 2 ? O22 Na1 Na2 O11 -103.58(5) . . . 2 ? O22 Na1 Na2 O11 11.01(7) 2_554 . . 2 ? N2 Na1 Na2 O11 -96.24(4) . . . 2 ? C17 Na1 Na2 O11 65.34(4) . . . 2 ? Na2 Na1 Na2 O11 22.57(4) 2_554 . . 2 ? Na2 Na1 Na2 O11 123.44(3) 2_544 . . 2 ? O21 Na1 Na2 O22 -96.92(5) 2_544 . . . ? O12 Na1 Na2 O22 -168.65(6) . . . . ? O01 Na1 Na2 O22 93.11(5) . . . . ? O22 Na1 Na2 O22 114.58(7) 2_554 . . . ? N2 Na1 Na2 O22 7.34(4) . . . . ? C17 Na1 Na2 O22 168.92(5) . . . . ? Na2 Na1 Na2 O22 126.15(4) 2_554 . . . ? Na2 Na1 Na2 O22 -132.98(4) 2_544 . . . ? O21 Na1 Na2 O12 -21.59(7) 2_544 . . 2_545 ? O12 Na1 Na2 O12 -93.32(6) . . . 2_545 ? O01 Na1 Na2 O12 168.44(7) . . . 2_545 ? O22 Na1 Na2 O12 75.33(7) . . . 2_545 ? O22 Na1 Na2 O12 -170.08(8) 2_554 . . 2_545 ? N2 Na1 Na2 O12 82.67(7) . . . 2_545 ? C17 Na1 Na2 O12 -115.75(7) . . . 2_545 ? Na2 Na1 Na2 O12 -158.52(5) 2_554 . . 2_545 ? Na2 Na1 Na2 O12 -57.65(7) 2_544 . . 2_545 ? O21 Na1 Na2 O01 -126.98(4) 2_544 . . 2 ? O12 Na1 Na2 O01 161.29(5) . . . 2 ? O01 Na1 Na2 O01 63.04(3) . . . 2 ? O22 Na1 Na2 O01 -30.06(5) . . . 2 ? O22 Na1 Na2 O01 84.52(7) 2_554 . . 2 ? N2 Na1 Na2 O01 -22.72(5) . . . 2 ? C17 Na1 Na2 O01 138.86(4) . . . 2 ? Na2 Na1 Na2 O01 96.08(4) 2_554 . . 2 ? Na2 Na1 Na2 O01 -163.04(3) 2_544 . . 2 ? O21 Na1 Na2 O12 71.73(5) 2_544 . . . ? O01 Na1 Na2 O12 -98.25(5) . . . . ? O22 Na1 Na2 O12 168.65(6) . . . . ? O22 Na1 Na2 O12 -76.77(8) 2_554 . . . ? N2 Na1 Na2 O12 175.99(5) . . . . ? C17 Na1 Na2 O12 -22.43(4) . . . . ? Na2 Na1 Na2 O12 -65.21(4) 2_554 . . . ? Na2 Na1 Na2 O12 35.67(3) 2_544 . . . ? O21 Na1 Na2 N1 67.11(4) 2_544 . . . ? O12 Na1 Na2 N1 -4.62(4) . . . . ? O01 Na1 Na2 N1 -102.86(4) . . . . ? O22 Na1 Na2 N1 164.03(5) . . . . ? O22 Na1 Na2 N1 -81.39(7) 2_554 . . . ? N2 Na1 Na2 N1 171.37(4) . . . . ? C17 Na1 Na2 N1 -27.05(4) . . . . ? Na2 Na1 Na2 N1 -69.83(3) 2_554 . . . ? Na2 Na1 Na2 N1 31.05(3) 2_544 . . . ? O21 Na1 Na2 O21 -51.25(3) 2_544 . . . ? O12 Na1 Na2 O21 -122.98(4) . . . . ? O01 Na1 Na2 O21 138.78(4) . . . . ? O22 Na1 Na2 O21 45.67(4) . . . . ? O22 Na1 Na2 O21 160.26(7) 2_554 . . . ? N2 Na1 Na2 O21 53.01(4) . . . . ? C17 Na1 Na2 O21 -145.41(4) . . . . ? Na2 Na1 Na2 O21 171.82(3) 2_554 . . . ? Na2 Na1 Na2 O21 -87.31(3) 2_544 . . . ? O21 Na1 Na2 C27 -70.80(4) 2_544 . . . ? O12 Na1 Na2 C27 -142.53(5) . . . . ? O01 Na1 Na2 C27 119.22(4) . . . . ? O22 Na1 Na2 C27 26.12(5) . . . . ? O22 Na1 Na2 C27 140.70(7) 2_554 . . . ? N2 Na1 Na2 C27 33.46(4) . . . . ? C17 Na1 Na2 C27 -164.96(4) . . . . ? Na2 Na1 Na2 C27 152.26(4) 2_554 . . . ? Na2 Na1 Na2 C27 -106.86(3) 2_544 . . . ? O21 Na1 Na2 Na1 -139.15(3) 2_544 . . 2 ? O12 Na1 Na2 Na1 149.12(4) . . . 2 ? O01 Na1 Na2 Na1 50.88(3) . . . 2 ? O22 Na1 Na2 Na1 -42.23(4) . . . 2 ? O22 Na1 Na2 Na1 72.35(7) 2_554 . . 2 ? N2 Na1 Na2 Na1 -34.89(3) . . . 2 ? C17 Na1 Na2 Na1 126.69(3) . . . 2 ? Na2 Na1 Na2 Na1 83.92(3) 2_554 . . 2 ? Na2 Na1 Na2 Na1 -175.210(15) 2_544 . . 2 ? O21 Na1 Na2 Na1 -38.17(4) 2_544 . . 2_545 ? O12 Na1 Na2 Na1 -109.90(4) . . . 2_545 ? O01 Na1 Na2 Na1 151.85(3) . . . 2_545 ? O22 Na1 Na2 Na1 58.75(4) . . . 2_545 ? O22 Na1 Na2 Na1 173.33(6) 2_554 . . 2_545 ? N2 Na1 Na2 Na1 66.09(3) . . . 2_545 ? C17 Na1 Na2 Na1 -132.33(3) . . . 2_545 ? Na2 Na1 Na2 Na1 -175.107(15) 2_554 . . 2_545 ? Na2 Na1 Na2 Na1 -74.23(3) 2_544 . . 2_545 ? O21 Na1 O12 C17 122.67(9) 2_544 . . . ? O01 Na1 O12 C17 -49.93(9) . . . . ? O22 Na1 O12 C17 -129.59(9) . . . . ? O22 Na1 O12 C17 25.17(10) 2_554 . . . ? N2 Na1 O12 C17 -130.14(10) . . . . ? Na2 Na1 O12 C17 -2.19(9) 2_554 . . . ? Na2 Na1 O12 C17 -122.32(10) . . . . ? Na2 Na1 O12 C17 118.59(11) 2_544 . . . ? O21 Na1 O12 Na2 4.08(5) 2_544 . . 2_544 ? O01 Na1 O12 Na2 -168.52(5) . . . 2_544 ? O22 Na1 O12 Na2 111.82(4) . . . 2_544 ? O22 Na1 O12 Na2 -93.42(5) 2_554 . . 2_544 ? N2 Na1 O12 Na2 111.27(8) . . . 2_544 ? C17 Na1 O12 Na2 -118.59(11) . . . 2_544 ? Na2 Na1 O12 Na2 -120.78(4) 2_554 . . 2_544 ? Na2 Na1 O12 Na2 119.09(5) . . . 2_544 ? O21 Na1 O12 Na2 -115.01(4) 2_544 . . . ? O01 Na1 O12 Na2 72.39(4) . . . . ? O22 Na1 O12 Na2 -7.27(4) . . . . ? O22 Na1 O12 Na2 147.49(4) 2_554 . . . ? N2 Na1 O12 Na2 -7.82(9) . . . . ? C17 Na1 O12 Na2 122.32(10) . . . . ? Na2 Na1 O12 Na2 120.13(3) 2_554 . . . ? Na2 Na1 O12 Na2 -119.09(5) 2_544 . . . ? O11 Na2 O12 C17 24.28(9) 2 . . . ? O22 Na2 O12 C17 119.66(9) . . . . ? O12 Na2 O12 C17 -115.74(8) 2_545 . . . ? O01 Na2 O12 C17 71.74(14) 2 . . . ? N1 Na2 O12 C17 -73.27(9) . . . . ? O21 Na2 O12 C17 166.14(9) . . . . ? C27 Na2 O12 C17 142.21(9) . . . . ? Na1 Na2 O12 C17 80.65(9) 2 . . . ? Na1 Na2 O12 C17 112.07(10) . . . . ? Na1 Na2 O12 C17 -159.70(8) 2_545 . . . ? O11 Na2 O12 Na1 -87.79(4) 2 . . . ? O22 Na2 O12 Na1 7.59(4) . . . . ? O12 Na2 O12 Na1 132.19(5) 2_545 . . . ? O01 Na2 O12 Na1 -40.33(11) 2 . . . ? N1 Na2 O12 Na1 174.66(5) . . . . ? O21 Na2 O12 Na1 54.07(4) . . . . ? C27 Na2 O12 Na1 30.14(4) . . . . ? Na1 Na2 O12 Na1 -31.42(4) 2 . . . ? Na1 Na2 O12 Na1 88.23(4) 2_545 . . . ? O11 Na2 O12 Na2 167.12(5) 2 . . 2_544 ? O22 Na2 O12 Na2 -97.51(5) . . . 2_544 ? O12 Na2 O12 Na2 27.09(10) 2_545 . . 2_544 ? O01 Na2 O12 Na2 -145.43(7) 2 . . 2_544 ? N1 Na2 O12 Na2 69.57(5) . . . 2_544 ? O21 Na2 O12 Na2 -51.03(5) . . . 2_544 ? C27 Na2 O12 Na2 -74.95(5) . . . 2_544 ? Na1 Na2 O12 Na2 -136.51(4) 2 . . 2_544 ? Na1 Na2 O12 Na2 -105.09(6) . . . 2_544 ? Na1 Na2 O12 Na2 -16.86(6) 2_545 . . 2_544 ? O11 Na2 O22 C27 -167.89(9) 2 . . . ? O12 Na2 O22 C27 -23.77(10) 2_545 . . . ? O01 Na2 O22 C27 -90.55(9) 2 . . . ? O12 Na2 O22 C27 108.78(9) . . . . ? N1 Na2 O22 C27 91.98(10) . . . . ? O21 Na2 O22 C27 1.93(8) . . . . ? Na1 Na2 O22 C27 -125.57(10) 2 . . . ? Na1 Na2 O22 C27 116.24(10) . . . . ? Na1 Na2 O22 C27 -9.72(8) 2_545 . . . ? O11 Na2 O22 Na1 75.87(4) 2 . . . ? O12 Na2 O22 Na1 -140.02(4) 2_545 . . . ? O01 Na2 O22 Na1 153.21(4) 2 . . . ? O12 Na2 O22 Na1 -7.46(4) . . . . ? N1 Na2 O22 Na1 -24.27(7) . . . . ? O21 Na2 O22 Na1 -114.32(5) . . . . ? C27 Na2 O22 Na1 -116.24(10) . . . . ? Na1 Na2 O22 Na1 118.19(4) 2 . . . ? Na1 Na2 O22 Na1 -125.97(3) 2_545 . . . ? O11 Na2 O22 Na1 -42.32(4) 2 . . 2 ? O12 Na2 O22 Na1 101.80(5) 2_545 . . 2 ? O01 Na2 O22 Na1 35.02(3) 2 . . 2 ? O12 Na2 O22 Na1 -125.65(4) . . . 2 ? N1 Na2 O22 Na1 -142.45(5) . . . 2 ? O21 Na2 O22 Na1 127.50(5) . . . 2 ? C27 Na2 O22 Na1 125.57(10) . . . 2 ? Na1 Na2 O22 Na1 -118.19(4) . . . 2 ? Na1 Na2 O22 Na1 115.84(3) 2_545 . . 2 ? O21 Na1 O22 C27 -15.42(10) 2_544 . . . ? O12 Na1 O22 C27 -103.37(9) . . . . ? O01 Na1 O22 C27 171.39(9) . . . . ? O22 Na1 O22 C27 114.14(9) 2_554 . . . ? N2 Na1 O22 C27 76.32(9) . . . . ? C17 Na1 O22 C27 -121.60(9) . . . . ? Na2 Na1 O22 C27 174.99(8) 2_554 . . . ? Na2 Na1 O22 C27 -111.65(10) . . . . ? Na2 Na1 O22 C27 -66.40(9) 2_544 . . . ? O21 Na1 O22 Na2 96.24(4) 2_544 . . . ? O12 Na1 O22 Na2 8.29(4) . . . . ? O01 Na1 O22 Na2 -76.96(4) . . . . ? O22 Na1 O22 Na2 -134.20(7) 2_554 . . . ? N2 Na1 O22 Na2 -172.02(5) . . . . ? C17 Na1 O22 Na2 -9.95(4) . . . . ? Na2 Na1 O22 Na2 -73.36(5) 2_554 . . . ? Na2 Na1 O22 Na2 45.25(4) 2_544 . . . ? O21 Na1 O22 Na1 -170.95(4) 2_544 . . 2 ? O12 Na1 O22 Na1 101.10(5) . . . 2 ? O01 Na1 O22 Na1 15.86(5) . . . 2 ? O22 Na1 O22 Na1 -41.39(11) 2_554 . . 2 ? N2 Na1 O22 Na1 -79.21(5) . . . 2 ? C17 Na1 O22 Na1 82.86(5) . . . 2 ? Na2 Na1 O22 Na1 19.46(7) 2_554 . . 2 ? Na2 Na1 O22 Na1 92.81(5) . . . 2 ? Na2 Na1 O22 Na1 138.06(4) 2_544 . . 2 ? O11 Na2 N1 C12 -13.07(10) 2 . . . ? O22 Na2 N1 C12 87.49(11) . . . . ? O12 Na2 N1 C12 -143.53(10) 2_545 . . . ? O01 Na2 N1 C12 -88.56(11) 2 . . . ? O12 Na2 N1 C12 67.91(9) . . . . ? O21 Na2 N1 C12 147.44(9) . . . . ? C27 Na2 N1 C12 121.79(10) . . . . ? Na1 Na2 N1 C12 -0.66(15) 2 . . . ? Na1 Na2 N1 C12 71.44(10) . . . . ? Na1 Na2 N1 C12 -176.65(9) 2_545 . . . ? Na2 N1 C12 C13 126.50(11) . . . . ? Na2 N1 C12 C11 -51.32(16) . . . . ? N2 C22 C21 C26 -177.88(12) . . . . ? C23 C22 C21 C26 -1.33(19) . . . . ? N2 C22 C21 C27 2.03(19) . . . . ? C23 C22 C21 C27 178.59(13) . . . . ? N1 C12 C11 C16 177.88(13) . . . . ? C13 C12 C11 C16 0.1(2) . . . . ? N1 C12 C11 C17 -6.1(2) . . . . ? C13 C12 C11 C17 176.09(12) . . . . ? C22 C21 C26 C25 -0.2(2) . . . . ? C27 C21 C26 C25 179.88(14) . . . . ? N2 C22 C23 C24 178.64(14) . . . . ? C21 C22 C23 C24 1.9(2) . . . . ? N1 C12 C13 C14 -178.04(14) . . . . ? C11 C12 C13 C14 -0.1(2) . . . . ? C22 C23 C24 C25 -1.0(2) . . . . ? Na2 O11 C17 O12 76.81(18) 2_554 . . . ? Na2 O11 C17 C11 -105.18(14) 2_554 . . . ? Na2 O11 C17 Na1 56.78(12) 2_554 . . . ? Na1 O12 C17 O11 -26.44(16) . . . . ? Na2 O12 C17 O11 85.45(13) 2_544 . . . ? Na2 O12 C17 O11 -129.85(12) . . . . ? Na1 O12 C17 C11 155.57(9) . . . . ? Na2 O12 C17 C11 -92.54(12) 2_544 . . . ? Na2 O12 C17 C11 52.16(14) . . . . ? Na2 O12 C17 Na1 111.88(9) 2_544 . . . ? Na2 O12 C17 Na1 -103.41(8) . . . . ? C16 C11 C17 O11 7.41(19) . . . . ? C12 C11 C17 O11 -168.61(13) . . . . ? C16 C11 C17 O12 -174.52(12) . . . . ? C12 C11 C17 O12 9.46(19) . . . . ? C16 C11 C17 Na1 -122.2(2) . . . . ? C12 C11 C17 Na1 61.8(3) . . . . ? O21 Na1 C17 O11 98.11(8) 2_544 . . . ? O12 Na1 C17 O11 157.35(14) . . . . ? O01 Na1 C17 O11 -76.79(8) . . . . ? O22 Na1 C17 O11 -151.02(8) . . . . ? O22 Na1 C17 O11 -1.07(8) 2_554 . . . ? N2 Na1 C17 O11 -105.31(12) . . . . ? Na2 Na1 C17 O11 -25.12(7) 2_554 . . . ? Na2 Na1 C17 O11 -158.24(8) . . . . ? Na2 Na1 C17 O11 113.75(8) 2_544 . . . ? O21 Na1 C17 O12 -59.25(10) 2_544 . . . ? O01 Na1 C17 O12 125.86(10) . . . . ? O22 Na1 C17 O12 51.62(9) . . . . ? O22 Na1 C17 O12 -158.42(9) 2_554 . . . ? N2 Na1 C17 O12 97.34(13) . . . . ? Na2 Na1 C17 O12 177.53(10) 2_554 . . . ? Na2 Na1 C17 O12 44.41(8) . . . . ? Na2 Na1 C17 O12 -43.61(8) 2_544 . . . ? O21 Na1 C17 C11 -125.9(2) 2_544 . . . ? O12 Na1 C17 C11 -66.7(2) . . . . ? O01 Na1 C17 C11 59.2(2) . . . . ? O22 Na1 C17 C11 -15.1(2) . . . . ? O22 Na1 C17 C11 134.9(2) 2_554 . . . ? N2 Na1 C17 C11 30.7(3) . . . . ? Na2 Na1 C17 C11 110.8(2) 2_554 . . . ? Na2 Na1 C17 C11 -22.3(2) . . . . ? Na2 Na1 C17 C11 -110.3(2) 2_544 . . . ? C12 C11 C16 C15 -0.3(2) . . . . ? C17 C11 C16 C15 -176.49(13) . . . . ? C21 C26 C25 C24 1.2(2) . . . . ? C23 C24 C25 C26 -0.6(2) . . . . ? C11 C16 C15 C14 0.6(2) . . . . ? C12 C13 C14 C15 0.4(2) . . . . ? C16 C15 C14 C13 -0.6(2) . . . . ? O11 Na2 O21 C27 14.82(11) 2 . . . ? O22 Na2 O21 C27 -1.86(7) . . . . ? O12 Na2 O21 C27 155.75(9) 2_545 . . . ? O01 Na2 O21 C27 79.34(8) 2 . . . ? O12 Na2 O21 C27 -74.56(8) . . . . ? N1 Na2 O21 C27 -132.34(8) . . . . ? Na1 Na2 O21 C27 33.92(8) 2 . . . ? Na1 Na2 O21 C27 -41.04(8) . . . . ? Na1 Na2 O21 C27 159.15(10) 2_545 . . . ? O11 Na2 O21 Na1 -144.33(6) 2 . . 2_545 ? O22 Na2 O21 Na1 -161.00(6) . . . 2_545 ? O12 Na2 O21 Na1 -3.40(4) 2_545 . . 2_545 ? O01 Na2 O21 Na1 -79.80(4) 2 . . 2_545 ? O12 Na2 O21 Na1 126.29(4) . . . 2_545 ? N1 Na2 O21 Na1 68.51(5) . . . 2_545 ? C27 Na2 O21 Na1 -159.15(10) . . . 2_545 ? Na1 Na2 O21 Na1 -125.22(4) 2 . . 2_545 ? Na1 Na2 O21 Na1 159.81(4) . . . 2_545 ? Na2 O22 C27 O21 -3.93(16) . . . . ? Na1 O22 C27 O21 102.71(14) . . . . ? Na1 O22 C27 O21 -103.58(14) 2 . . . ? Na2 O22 C27 C21 177.13(9) . . . . ? Na1 O22 C27 C21 -76.24(13) . . . . ? Na1 O22 C27 C21 77.47(14) 2 . . . ? Na1 O22 C27 Na2 106.64(8) . . . . ? Na1 O22 C27 Na2 -99.65(9) 2 . . . ? Na1 O21 C27 O22 78.0(3) 2_545 . . . ? Na2 O21 C27 O22 3.13(13) . . . . ? Na1 O21 C27 C21 -103.0(3) 2_545 . . . ? Na2 O21 C27 C21 -177.91(11) . . . . ? Na1 O21 C27 Na2 74.9(3) 2_545 . . . ? C26 C21 C27 O22 -161.89(13) . . . . ? C22 C21 C27 O22 18.20(19) . . . . ? C26 C21 C27 O21 19.12(18) . . . . ? C22 C21 C27 O21 -160.80(13) . . . . ? C26 C21 C27 Na2 -150.8(4) . . . . ? C22 C21 C27 Na2 29.3(5) . . . . ? O11 Na2 C27 O22 13.68(10) 2 . . . ? O12 Na2 C27 O22 159.59(9) 2_545 . . . ? O01 Na2 C27 O22 85.61(9) 2 . . . ? O12 Na2 C27 O22 -69.61(9) . . . . ? N1 Na2 C27 O22 -113.21(9) . . . . ? O21 Na2 C27 O22 -176.55(14) . . . . ? Na1 Na2 C27 O22 41.83(8) 2 . . . ? Na1 Na2 C27 O22 -46.19(8) . . . . ? Na1 Na2 C27 O22 169.01(10) 2_545 . . . ? O11 Na2 C27 O21 -169.77(8) 2 . . . ? O22 Na2 C27 O21 176.55(14) . . . . ? O12 Na2 C27 O21 -23.85(9) 2_545 . . . ? O01 Na2 C27 O21 -97.84(8) 2 . . . ? O12 Na2 C27 O21 106.94(8) . . . . ? N1 Na2 C27 O21 63.34(10) . . . . ? Na1 Na2 C27 O21 -141.61(9) 2 . . . ? Na1 Na2 C27 O21 130.36(9) . . . . ? Na1 Na2 C27 O21 -14.44(7) 2_545 . . . ? O11 Na2 C27 C21 0.9(5) 2 . . . ? O22 Na2 C27 C21 -12.7(4) . . . . ? O12 Na2 C27 C21 146.8(5) 2_545 . . . ? O01 Na2 C27 C21 72.9(5) 2 . . . ? O12 Na2 C27 C21 -82.4(5) . . . . ? N1 Na2 C27 C21 -126.0(4) . . . . ? O21 Na2 C27 C21 170.7(5) . . . . ? Na1 Na2 C27 C21 29.1(4) 2 . . . ? Na1 Na2 C27 C21 -58.9(4) . . . . ? Na1 Na2 C27 C21 156.3(5) 2_545 . . . ? C23 C22 N2 Na1 -142.60(11) . . . . ? C21 C22 N2 Na1 33.95(16) . . . . ? O21 Na1 N2 C22 48.85(11) 2_544 . . . ? O12 Na1 N2 C22 -55.74(14) . . . . ? O01 Na1 N2 C22 -134.60(11) . . . . ? O22 Na1 N2 C22 -56.36(10) . . . . ? O22 Na1 N2 C22 145.15(10) 2_554 . . . ? C17 Na1 N2 C22 -107.93(13) . . . . ? Na2 Na1 N2 C22 -177.80(9) 2_554 . . . ? Na2 Na1 N2 C22 -61.60(10) . . . . ? Na2 Na1 N2 C22 16.85(14) 2_544 . . . ? O21 Na1 O01 Na2 38.6(3) 2_544 . . 2_554 ? O12 Na1 O01 Na2 88.87(4) . . . 2_554 ? O22 Na1 O01 Na2 176.10(4) . . . 2_554 ? O22 Na1 O01 Na2 -34.50(4) 2_554 . . 2_554 ? N2 Na1 O01 Na2 -120.66(4) . . . 2_554 ? C17 Na1 O01 Na2 69.95(4) . . . 2_554 ? Na2 Na1 O01 Na2 135.44(4) . . . 2_554 ? Na2 Na1 O01 Na2 80.15(4) 2_544 . . 2_554 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H04 O12 0.92(2) 2.05(2) 2.6780(17) 124.5(17) . N1 H04 O01 0.92(2) 2.44(2) 3.1778(16) 137.7(18) 1_545 O01 H02 O11 0.81(4) 1.98(4) 2.7828(15) 171(3) 2 N2 H06 O22 0.90(3) 2.19(2) 2.7134(16) 116.1(19) . N2 H06 O21 0.90(3) 2.44(3) 3.1916(17) 141(2) 1_565 N1 H03 O11 0.82(3) 2.63(3) 3.1504(15) 122(2) 2_545 O01 H01 O21 0.82(3) 1.98(3) 2.7920(16) 169(3) 1_565 _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 27.16 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.286 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.055 data_wies10 _database_code_CSD 193294 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H7 Li N O2.50' _chemical_formula_weight 152.08 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.2250(1) _cell_length_b 9.1650(2) _cell_length_c 15.2200(5) _cell_angle_alpha 75.638(1) _cell_angle_beta 87.278(1) _cell_angle_gamma 84.999(2) _cell_volume 703.12(3) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 19977 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.107 _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 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19977 _diffrn_reflns_av_R_equivalents 0.028 _diffrn_reflns_av_sigmaI/netI 0.0270 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.92 _diffrn_reflns_theta_max 27.21 _reflns_number_total 2913 _reflns_number_gt 2677 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All acidic protons were found; distances for the protons of the water molecule were fixed before isotropic refinement. ; _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^)+(0.0548P)^2^+0.3677P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2913 _refine_ls_number_parameters 232 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0473 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1144 _refine_ls_wR_factor_gt 0.1112 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 O22 O 0.09962(19) 0.81924(11) 0.41149(6) 0.0208(2) Uani 1 1 d . . . O12 O 0.3601(2) 1.11310(11) 0.42376(6) 0.0229(2) Uani 1 1 d . . . O21 O -0.3152(2) 0.82900(13) 0.38462(7) 0.0267(3) Uani 1 1 d . . . O11 O 0.7305(2) 1.21521(13) 0.40621(7) 0.0302(3) Uani 1 1 d . . . N2 N 0.3703(2) 0.64019(13) 0.30417(8) 0.0205(3) Uani 1 1 d . . . C22 C 0.1930(3) 0.72151(15) 0.23959(9) 0.0186(3) Uani 1 1 d . . . N1 N 0.8089(3) 1.41960(15) 0.24064(10) 0.0293(3) Uani 1 1 d . . . C27 C -0.0832(3) 0.81949(14) 0.35977(9) 0.0178(3) Uani 1 1 d . . . C24 C 0.0487(3) 0.78375(18) 0.08429(9) 0.0272(3) Uani 1 1 d . . . H24 H 0.0741 0.7754 0.0235 0.033 Uiso 1 1 calc R . . C21 C -0.0242(3) 0.80654(15) 0.26383(8) 0.0179(3) Uani 1 1 d . . . C16 C 0.3088(3) 1.15702(16) 0.23871(10) 0.0242(3) Uani 1 1 d . . . H16 H 0.2052 1.0898 0.2801 0.029 Uiso 1 1 calc R . . C17 C 0.5331(3) 1.18484(15) 0.37303(9) 0.0191(3) Uani 1 1 d . . . C11 C 0.4957(3) 1.22931(15) 0.27296(9) 0.0197(3) Uani 1 1 d . . . C26 C -0.2001(3) 0.87874(16) 0.19731(9) 0.0224(3) Uani 1 1 d . . . H26 H -0.3478 0.9352 0.2138 0.027 Uiso 1 1 calc R . . C23 C 0.2235(3) 0.71015(16) 0.14936(9) 0.0234(3) Uani 1 1 d . . . H23 H 0.3669 0.6508 0.1326 0.028 Uiso 1 1 calc R . . C14 C 0.4240(3) 1.28166(18) 0.08716(10) 0.0311(4) Uani 1 1 d . . . H14 H 0.4027 1.2985 0.0237 0.037 Uiso 1 1 calc R . . C25 C -0.1644(3) 0.86996(17) 0.10783(10) 0.0269(3) Uani 1 1 d . . . H25 H -0.2834 0.9220 0.0632 0.032 Uiso 1 1 calc R . . C13 C 0.6035(3) 1.35686(17) 0.11795(10) 0.0294(3) Uani 1 1 d . . . H13 H 0.7024 1.4255 0.0756 0.035 Uiso 1 1 calc R . . C12 C 0.6429(3) 1.33324(16) 0.21198(10) 0.0236(3) Uani 1 1 d . . . C15 C 0.2728(3) 1.18145(18) 0.14678(10) 0.0287(3) Uani 1 1 d . . . H15 H 0.1478 1.1311 0.1247 0.034 Uiso 1 1 calc R . . Li1 Li 0.4036(5) 0.8900(3) 0.45459(16) 0.0218(5) Uani 1 1 d . . . Li2 Li 1.0525(5) 1.2197(3) 0.46301(16) 0.0231(5) Uani 1 1 d . . . H04 H 0.510(4) 0.600(2) 0.2792(13) 0.033(5) Uiso 1 1 d . . . H03 H 0.426(4) 0.697(2) 0.3406(14) 0.037(5) Uiso 1 1 d . . . O01 O 1.1287(4) 1.42814(15) 0.43565(11) 0.0614(5) Uani 1 1 d D . . H01 H 0.874(4) 1.381(3) 0.2984(16) 0.046(6) Uiso 1 1 d . . . H02 H 0.930(5) 1.461(3) 0.1942(16) 0.054(6) Uiso 1 1 d . . . H05 H 1.206(5) 1.494(3) 0.3887(14) 0.084(9) Uiso 1 1 d D . . H06 H 1.10(2) 1.451(14) 0.491(4) 0.40(6) Uiso 1 1 d 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 O22 0.0194(5) 0.0269(5) 0.0175(5) -0.0077(4) -0.0013(3) -0.0034(4) O12 0.0261(6) 0.0206(5) 0.0201(5) -0.0037(4) 0.0046(4) 0.0017(4) O21 0.0179(6) 0.0417(6) 0.0251(5) -0.0176(4) 0.0025(4) -0.0013(4) O11 0.0281(6) 0.0368(6) 0.0276(6) -0.0099(4) -0.0099(4) -0.0021(4) N2 0.0197(7) 0.0212(6) 0.0215(6) -0.0078(4) -0.0002(4) 0.0010(4) C22 0.0201(7) 0.0183(6) 0.0183(6) -0.0059(5) 0.0008(5) -0.0037(5) N1 0.0277(8) 0.0288(7) 0.0312(7) -0.0065(5) 0.0024(5) -0.0051(5) C27 0.0184(7) 0.0173(6) 0.0186(6) -0.0064(5) 0.0004(5) -0.0014(5) C24 0.0320(9) 0.0354(8) 0.0163(6) -0.0095(6) 0.0021(5) -0.0058(6) C21 0.0187(7) 0.0194(6) 0.0167(6) -0.0062(5) 0.0009(5) -0.0037(5) C16 0.0263(8) 0.0244(7) 0.0210(7) -0.0052(5) -0.0018(5) 0.0025(5) C17 0.0220(7) 0.0186(6) 0.0172(6) -0.0070(5) -0.0010(5) 0.0034(5) C11 0.0232(8) 0.0193(6) 0.0159(6) -0.0050(5) -0.0001(5) 0.0041(5) C26 0.0213(8) 0.0247(7) 0.0215(7) -0.0068(5) -0.0012(5) -0.0005(5) C23 0.0244(8) 0.0270(7) 0.0210(7) -0.0107(5) 0.0046(5) -0.0028(5) C14 0.0407(10) 0.0309(8) 0.0199(7) -0.0055(6) -0.0007(6) 0.0047(7) C25 0.0291(9) 0.0324(8) 0.0189(7) -0.0049(6) -0.0047(5) -0.0029(6) C13 0.0353(9) 0.0269(7) 0.0239(7) -0.0044(6) 0.0041(6) 0.0015(6) C12 0.0249(8) 0.0208(6) 0.0239(7) -0.0055(5) 0.0029(5) 0.0027(5) C15 0.0323(9) 0.0309(8) 0.0245(7) -0.0098(6) -0.0070(6) -0.0001(6) Li1 0.0216(13) 0.0241(11) 0.0204(11) -0.0071(9) 0.0009(9) -0.0017(9) Li2 0.0229(13) 0.0239(12) 0.0225(11) -0.0064(9) 0.0018(9) -0.0012(9) O01 0.1072(14) 0.0235(6) 0.0537(9) -0.0143(6) 0.0503(9) -0.0199(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 O22 C27 1.2660(17) . ? O22 Li1 1.966(3) . ? O22 Li2 1.994(3) 2_676 ? O12 C17 1.2768(17) . ? O12 Li2 1.954(3) 1_455 ? O12 Li1 1.976(3) . ? O12 Li1 2.266(3) 2_676 ? O21 C27 1.2546(17) . ? O21 Li1 1.900(3) 1_455 ? O21 Li2 2.673(3) 2_676 ? O11 C17 1.2513(18) . ? O11 Li2 1.936(3) . ? O11 Li1 2.207(3) 2_676 ? N2 C22 1.4081(18) . ? N2 H04 0.90(2) . ? N2 H03 0.92(2) . ? C22 C23 1.4034(18) . ? C22 C21 1.4071(19) . ? N1 C12 1.377(2) . ? N1 H01 0.93(2) . ? N1 H02 0.96(3) . ? C27 C21 1.5094(17) . ? C27 Li2 2.642(3) 2_676 ? C24 C23 1.384(2) . ? C24 C25 1.393(2) . ? C24 H24 0.9500 . ? C21 C26 1.3994(19) . ? C16 C15 1.380(2) . ? C16 C11 1.413(2) . ? C16 H16 0.9500 . ? C17 C11 1.4935(17) . ? C17 Li1 2.571(3) 2_676 ? C11 C12 1.408(2) . ? C26 C25 1.3869(19) . ? C26 H26 0.9500 . ? C23 H23 0.9500 . ? C14 C13 1.374(2) . ? C14 C15 1.392(2) . ? C14 H14 0.9500 . ? C25 H25 0.9500 . ? C13 C12 1.416(2) . ? C13 H13 0.9500 . ? C15 H15 0.9500 . ? Li1 O21 1.900(3) 1_655 ? Li1 O11 2.207(3) 2_676 ? Li1 O12 2.266(3) 2_676 ? Li1 C17 2.571(3) 2_676 ? Li1 Li2 2.788(4) 2_676 ? Li1 Li1 2.976(5) 2_676 ? Li1 Li2 3.142(4) 2_776 ? Li1 Li2 3.423(3) 1_455 ? Li2 O01 1.924(3) . ? Li2 O12 1.954(3) 1_655 ? Li2 O22 1.994(3) 2_676 ? Li2 C27 2.642(3) 2_676 ? Li2 O21 2.673(3) 2_676 ? Li2 Li1 2.788(4) 2_676 ? Li2 Li1 3.142(4) 2_776 ? Li2 Li1 3.423(3) 1_655 ? Li2 H06 2.30(11) . ? O01 H05 0.918(5) . ? O01 H06 0.919(5) . ? 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 C27 O22 Li1 157.66(12) . . ? C27 O22 Li2 106.14(11) . 2_676 ? Li1 O22 Li2 89.52(11) . 2_676 ? C17 O12 Li2 121.16(11) . 1_455 ? C17 O12 Li1 117.61(11) . . ? Li2 O12 Li1 121.12(11) 1_455 . ? C17 O12 Li1 88.47(10) . 2_676 ? Li2 O12 Li1 95.93(10) 1_455 2_676 ? Li1 O12 Li1 88.82(10) . 2_676 ? C27 O21 Li1 154.42(12) . 1_455 ? C27 O21 Li2 75.00(9) . 2_676 ? Li1 O21 Li2 85.04(10) 1_455 2_676 ? C17 O11 Li2 168.73(13) . . ? C17 O11 Li1 91.81(11) . 2_676 ? Li2 O11 Li1 84.32(10) . 2_676 ? C22 N2 H04 113.1(12) . . ? C22 N2 H03 113.4(12) . . ? H04 N2 H03 107.6(18) . . ? C23 C22 C21 118.60(12) . . ? C23 C22 N2 119.34(12) . . ? C21 C22 N2 121.93(12) . . ? C12 N1 H01 116.5(14) . . ? C12 N1 H02 112.4(15) . . ? H01 N1 H02 116(2) . . ? O21 C27 O22 122.96(12) . . ? O21 C27 C21 117.52(12) . . ? O22 C27 C21 119.52(12) . . ? O21 C27 Li2 77.70(9) . 2_676 ? O22 C27 Li2 46.46(8) . 2_676 ? C21 C27 Li2 161.36(11) . 2_676 ? C23 C24 C25 120.16(13) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C26 C21 C22 119.21(12) . . ? C26 C21 C27 117.72(12) . . ? C22 C21 C27 123.03(12) . . ? C15 C16 C11 121.78(14) . . ? C15 C16 H16 119.1 . . ? C11 C16 H16 119.1 . . ? O11 C17 O12 120.85(12) . . ? O11 C17 C11 120.87(13) . . ? O12 C17 C11 118.28(12) . . ? O11 C17 Li1 59.09(9) . 2_676 ? O12 C17 Li1 61.77(9) . 2_676 ? C11 C17 Li1 179.63(11) . 2_676 ? C12 C11 C16 119.21(13) . . ? C12 C11 C17 123.54(13) . . ? C16 C11 C17 117.20(12) . . ? C25 C26 C21 121.64(13) . . ? C25 C26 H26 119.2 . . ? C21 C26 H26 119.2 . . ? C24 C23 C22 121.32(13) . . ? C24 C23 H23 119.3 . . ? C22 C23 H23 119.3 . . ? C13 C14 C15 121.53(14) . . ? C13 C14 H14 119.2 . . ? C15 C14 H14 119.2 . . ? C26 C25 C24 119.03(13) . . ? C26 C25 H25 120.5 . . ? C24 C25 H25 120.5 . . ? C14 C13 C12 120.83(14) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? N1 C12 C11 122.45(13) . . ? N1 C12 C13 119.17(14) . . ? C11 C12 C13 118.21(14) . . ? C16 C15 C14 118.39(15) . . ? C16 C15 H15 120.8 . . ? C14 C15 H15 120.8 . . ? O21 Li1 O22 105.23(12) 1_655 . ? O21 Li1 O12 108.65(12) 1_655 . ? O22 Li1 O12 107.10(12) . . ? O21 Li1 O11 129.94(13) 1_655 2_676 ? O22 Li1 O11 87.35(10) . 2_676 ? O12 Li1 O11 113.41(11) . 2_676 ? O21 Li1 O12 95.18(11) 1_655 2_676 ? O22 Li1 O12 146.01(13) . 2_676 ? O12 Li1 O12 91.18(10) . 2_676 ? O11 Li1 O12 58.86(7) 2_676 2_676 ? O21 Li1 C17 114.75(12) 1_655 2_676 ? O22 Li1 C17 116.35(11) . 2_676 ? O12 Li1 C17 104.38(10) . 2_676 ? O11 Li1 C17 29.10(5) 2_676 2_676 ? O12 Li1 C17 29.76(5) 2_676 2_676 ? O21 Li1 Li2 138.84(13) 1_655 2_676 ? O22 Li1 Li2 45.65(8) . 2_676 ? O12 Li1 Li2 108.14(11) . 2_676 ? O11 Li1 Li2 43.71(7) 2_676 2_676 ? O12 Li1 Li2 101.87(10) 2_676 2_676 ? C17 Li1 Li2 72.46(8) 2_676 2_676 ? O21 Li1 Li1 106.33(14) 1_655 2_676 ? O22 Li1 Li1 145.75(16) . 2_676 ? O12 Li1 Li1 49.59(8) . 2_676 ? O11 Li1 Li1 82.53(10) 2_676 2_676 ? O12 Li1 Li1 41.60(7) 2_676 2_676 ? C17 Li1 Li1 60.25(8) 2_676 2_676 ? Li2 Li1 Li1 111.31(13) 2_676 2_676 ? O21 Li1 Li2 57.93(8) 1_655 2_776 ? O22 Li1 Li2 142.91(12) . 2_776 ? O12 Li1 Li2 109.65(11) . 2_776 ? O11 Li1 Li2 82.77(9) 2_676 2_776 ? O12 Li1 Li2 38.22(6) 2_676 2_776 ? C17 Li1 Li2 58.46(7) 2_676 2_776 ? Li2 Li1 Li2 123.43(11) 2_676 2_776 ? Li1 Li1 Li2 67.98(10) 2_676 2_776 ? O21 Li1 Li2 137.04(12) 1_655 1_455 ? O22 Li1 Li2 89.23(10) . 1_455 ? O12 Li1 Li2 29.26(6) . 1_455 ? O11 Li1 Li2 90.14(9) 2_676 1_455 ? O12 Li1 Li2 94.07(9) 2_676 1_455 ? C17 Li1 Li2 92.79(8) 2_676 1_455 ? Li2 Li1 Li2 79.06(9) 2_676 1_455 ? Li1 Li1 Li2 58.31(9) 2_676 1_455 ? Li2 Li1 Li2 126.29(8) 2_776 1_455 ? O01 Li2 O11 106.51(14) . . ? O01 Li2 O12 104.95(13) . 1_655 ? O11 Li2 O12 118.62(13) . 1_655 ? O01 Li2 O22 104.26(12) . 2_676 ? O11 Li2 O22 94.55(12) . 2_676 ? O12 Li2 O22 126.06(13) 1_655 2_676 ? O01 Li2 C27 94.16(11) . 2_676 ? O11 Li2 C27 121.95(12) . 2_676 ? O12 Li2 C27 106.49(11) 1_655 2_676 ? O22 Li2 C27 27.40(5) 2_676 2_676 ? O01 Li2 O21 88.86(11) . 2_676 ? O11 Li2 O21 148.34(13) . 2_676 ? O12 Li2 O21 82.08(9) 1_655 2_676 ? O22 Li2 O21 54.34(7) 2_676 2_676 ? C27 Li2 O21 27.30(4) 2_676 2_676 ? O01 Li2 Li1 124.71(13) . 2_676 ? O11 Li2 Li1 51.98(8) . 2_676 ? O12 Li2 Li1 130.33(12) 1_655 2_676 ? O22 Li2 Li1 44.83(8) 2_676 2_676 ? C27 Li2 Li1 71.46(8) 2_676 2_676 ? O21 Li2 Li1 96.47(9) 2_676 2_676 ? O01 Li2 Li1 91.98(12) . 2_776 ? O11 Li2 Li1 159.56(12) . 2_776 ? O12 Li2 Li1 45.85(7) 1_655 2_776 ? O22 Li2 Li1 89.09(10) 2_676 2_776 ? C27 Li2 Li1 63.64(7) 2_676 2_776 ? O21 Li2 Li1 37.04(6) 2_676 2_776 ? Li1 Li2 Li1 123.43(11) 2_676 2_776 ? O01 Li2 Li1 134.00(13) . 1_655 ? O11 Li2 Li1 106.03(10) . 1_655 ? O12 Li2 Li1 29.62(6) 1_655 1_655 ? O22 Li2 Li1 104.60(10) 2_676 1_655 ? C27 Li2 Li1 95.34(8) 2_676 1_655 ? O21 Li2 Li1 79.88(8) 2_676 1_655 ? Li1 Li2 Li1 100.94(9) 2_676 1_655 ? Li1 Li2 Li1 53.71(8) 2_776 1_655 ? O01 Li2 H06 22.9(19) . . ? O11 Li2 H06 113(2) . . ? O12 Li2 H06 117(3) 1_655 . ? O22 Li2 H06 82(2) 2_676 . ? C27 Li2 H06 72.1(19) 2_676 . ? O21 Li2 H06 72(2) 2_676 . ? Li1 Li2 H06 110(2) 2_676 . ? Li1 Li2 H06 88(3) 2_776 . ? Li1 Li2 H06 140(3) 1_655 . ? Li2 O01 H05 136.5(19) . . ? Li2 O01 H06 102(8) . . ? H05 O01 H06 120(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Li1 O21 C27 O22 28.9(4) 1_455 . . . ? Li2 O21 C27 O22 -10.98(13) 2_676 . . . ? Li1 O21 C27 C21 -151.6(2) 1_455 . . . ? Li2 O21 C27 C21 168.49(13) 2_676 . . . ? Li1 O21 C27 Li2 39.9(3) 1_455 . . 2_676 ? Li1 O22 C27 O21 -118.1(3) . . . . ? Li2 O22 C27 O21 14.87(17) 2_676 . . . ? Li1 O22 C27 C21 62.5(3) . . . . ? Li2 O22 C27 C21 -164.59(12) 2_676 . . . ? Li1 O22 C27 Li2 -132.9(3) . . . 2_676 ? C23 C22 C21 C26 -1.0(2) . . . . ? N2 C22 C21 C26 -176.82(13) . . . . ? C23 C22 C21 C27 176.68(12) . . . . ? N2 C22 C21 C27 0.8(2) . . . . ? O21 C27 C21 C26 31.81(18) . . . . ? O22 C27 C21 C26 -148.71(13) . . . . ? Li2 C27 C21 C26 174.2(3) 2_676 . . . ? O21 C27 C21 C22 -145.89(14) . . . . ? O22 C27 C21 C22 33.59(19) . . . . ? Li2 C27 C21 C22 -3.5(4) 2_676 . . . ? Li2 O11 C17 O12 68.1(7) . . . . ? Li1 O11 C17 O12 -1.45(14) 2_676 . . . ? Li2 O11 C17 C11 -110.8(6) . . . . ? Li1 O11 C17 C11 179.57(12) 2_676 . . . ? Li2 O11 C17 Li1 69.6(6) . . . 2_676 ? Li2 O12 C17 O11 97.42(16) 1_455 . . . ? Li1 O12 C17 O11 -86.45(16) . . . . ? Li1 O12 C17 O11 1.41(14) 2_676 . . . ? Li2 O12 C17 C11 -83.57(15) 1_455 . . . ? Li1 O12 C17 C11 92.55(14) . . . . ? Li1 O12 C17 C11 -179.58(12) 2_676 . . . ? Li2 O12 C17 Li1 96.01(13) 1_455 . . 2_676 ? Li1 O12 C17 Li1 -87.86(12) . . . 2_676 ? C15 C16 C11 C12 2.3(2) . . . . ? C15 C16 C11 C17 -175.03(13) . . . . ? O11 C17 C11 C12 -14.2(2) . . . . ? O12 C17 C11 C12 166.84(12) . . . . ? Li1 C17 C11 C12 69(20) 2_676 . . . ? O11 C17 C11 C16 163.08(13) . . . . ? O12 C17 C11 C16 -15.92(18) . . . . ? Li1 C17 C11 C16 -113(20) 2_676 . . . ? C22 C21 C26 C25 -0.7(2) . . . . ? C27 C21 C26 C25 -178.51(13) . . . . ? C25 C24 C23 C22 -0.7(2) . . . . ? C21 C22 C23 C24 1.7(2) . . . . ? N2 C22 C23 C24 177.65(13) . . . . ? C21 C26 C25 C24 1.7(2) . . . . ? C23 C24 C25 C26 -1.0(2) . . . . ? C15 C14 C13 C12 0.8(2) . . . . ? C16 C11 C12 N1 173.03(13) . . . . ? C17 C11 C12 N1 -9.8(2) . . . . ? C16 C11 C12 C13 -2.3(2) . . . . ? C17 C11 C12 C13 174.90(12) . . . . ? C14 C13 C12 N1 -174.68(14) . . . . ? C14 C13 C12 C11 0.8(2) . . . . ? C11 C16 C15 C14 -0.8(2) . . . . ? C13 C14 C15 C16 -0.8(2) . . . . ? C27 O22 Li1 O21 -79.1(3) . . . 1_655 ? Li2 O22 Li1 O21 145.59(12) 2_676 . . 1_655 ? C27 O22 Li1 O12 36.4(3) . . . . ? Li2 O22 Li1 O12 -98.91(12) 2_676 . . . ? C27 O22 Li1 O11 150.1(3) . . . 2_676 ? Li2 O22 Li1 O11 14.79(10) 2_676 . . 2_676 ? C27 O22 Li1 O12 156.1(2) . . . 2_676 ? Li2 O22 Li1 O12 20.7(2) 2_676 . . 2_676 ? C27 O22 Li1 C17 152.7(2) . . . 2_676 ? Li2 O22 Li1 C17 17.34(13) 2_676 . . 2_676 ? C27 O22 Li1 Li2 135.3(3) . . . 2_676 ? C27 O22 Li1 Li1 77.5(4) . . . 2_676 ? Li2 O22 Li1 Li1 -57.8(3) 2_676 . . 2_676 ? C27 O22 Li1 Li2 -135.6(3) . . . 2_776 ? Li2 O22 Li1 Li2 89.12(19) 2_676 . . 2_776 ? C27 O22 Li1 Li2 59.9(3) . . . 1_455 ? Li2 O22 Li1 Li2 -75.39(10) 2_676 . . 1_455 ? C17 O12 Li1 O21 -8.22(17) . . . 1_655 ? Li2 O12 Li1 O21 167.91(12) 1_455 . . 1_655 ? Li1 O12 Li1 O21 -95.87(13) 2_676 . . 1_655 ? C17 O12 Li1 O22 -121.42(13) . . . . ? Li2 O12 Li1 O22 54.71(16) 1_455 . . . ? Li1 O12 Li1 O22 150.93(15) 2_676 . . . ? C17 O12 Li1 O11 143.96(12) . . . 2_676 ? Li2 O12 Li1 O11 -39.91(18) 1_455 . . 2_676 ? Li1 O12 Li1 O11 56.31(9) 2_676 . . 2_676 ? C17 O12 Li1 O12 87.65(12) . . . 2_676 ? Li2 O12 Li1 O12 -96.22(13) 1_455 . . 2_676 ? Li1 O12 Li1 O12 0.0 2_676 . . 2_676 ? C17 O12 Li1 C17 114.64(11) . . . 2_676 ? Li2 O12 Li1 C17 -69.23(15) 1_455 . . 2_676 ? Li1 O12 Li1 C17 26.99(6) 2_676 . . 2_676 ? C17 O12 Li1 Li2 -169.44(11) . . . 2_676 ? Li2 O12 Li1 Li2 6.69(19) 1_455 . . 2_676 ? Li1 O12 Li1 Li2 102.91(12) 2_676 . . 2_676 ? C17 O12 Li1 Li1 87.65(12) . . . 2_676 ? Li2 O12 Li1 Li1 -96.22(13) 1_455 . . 2_676 ? C17 O12 Li1 Li2 53.45(14) . . . 2_776 ? Li2 O12 Li1 Li2 -130.42(10) 1_455 . . 2_776 ? Li1 O12 Li1 Li2 -34.20(7) 2_676 . . 2_776 ? C17 O12 Li1 Li2 -176.13(18) . . . 1_455 ? Li1 O12 Li1 Li2 96.22(13) 2_676 . . 1_455 ? C17 O11 Li2 O01 168.2(6) . . . . ? Li1 O11 Li2 O01 -121.47(12) 2_676 . . . ? C17 O11 Li2 O12 50.3(7) . . . 1_655 ? Li1 O11 Li2 O12 120.61(14) 2_676 . . 1_655 ? C17 O11 Li2 O22 -85.4(6) . . . 2_676 ? Li1 O11 Li2 O22 -15.13(10) 2_676 . . 2_676 ? C17 O11 Li2 C27 -85.9(7) . . . 2_676 ? Li1 O11 Li2 C27 -15.56(13) 2_676 . . 2_676 ? C17 O11 Li2 O21 -75.6(7) . . . 2_676 ? Li1 O11 Li2 O21 -5.3(2) 2_676 . . 2_676 ? C17 O11 Li2 Li1 -70.3(6) . . . 2_676 ? C17 O11 Li2 Li1 14.2(9) . . . 2_776 ? Li1 O11 Li2 Li1 84.5(4) 2_676 . . 2_776 ? C17 O11 Li2 Li1 21.2(7) . . . 1_655 ? Li1 O11 Li2 Li1 91.49(10) 2_676 . . 1_655 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H04 N1 0.90(2) 2.34(2) 3.1977(18) 160.2(17) 1_545 N2 H03 O21 0.92(2) 2.13(2) 2.9886(16) 155.9(18) 1_655 N2 H03 O22 0.92(2) 2.33(2) 2.8403(15) 114.7(15) . N1 H01 O11 0.93(2) 2.10(2) 2.7787(18) 128.7(18) . O01 H05 N2 0.918(5) 1.850(7) 2.7629(17) 173(3) 1_665 O01 H06 O01 0.919(5) 2.05(6) 2.846(3) 144(9) 2_786 _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 27.21 _diffrn_measured_fraction_theta_full 0.927 _refine_diff_density_max 0.391 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.048 data_wies7 _database_code_CSD 193295 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H8 K N O3' _chemical_formula_weight 193.24 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' _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 14.7016(3) _cell_length_b 7.6112(1) _cell_length_c 7.4325(1) _cell_angle_alpha 90.00 _cell_angle_beta 96.897(1) _cell_angle_gamma 90.00 _cell_volume 825.65(2) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 36873 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.607 _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 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius DIP 2020' _diffrn_measurement_method phi-rotation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36873 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.85 _diffrn_reflns_theta_max 31.92 _reflns_number_total 2822 _reflns_number_gt 2717 _reflns_threshold_expression >2sigma(I) _computing_data_collection XPRESS _computing_cell_refinement DENZO _computing_data_reduction SCALEPACK _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0765P)^2^+0.3449P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2822 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1221 _refine_ls_wR_factor_gt 0.1202 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 K1 K 0.480641(17) 0.75009(3) 0.43331(3) 0.01927(11) Uani 1 1 d . . . C1 C 0.24868(7) 1.05107(14) 0.23037(15) 0.0174(2) Uani 1 1 d . . . O1 O 0.39493(6) 0.97129(12) 0.14421(13) 0.02225(19) Uani 1 1 d . . . C7 C 0.34937(7) 1.08405(14) 0.21966(15) 0.0170(2) Uani 1 1 d . . . C6 C 0.20616(9) 1.14841(17) 0.35620(17) 0.0232(2) Uani 1 1 d . . . N1 N 0.23415(8) 0.82005(16) -0.00228(16) 0.0259(2) Uani 1 1 d . . . C2 C 0.19646(8) 0.92639(15) 0.12186(16) 0.0194(2) Uani 1 1 d . . . C3 C 0.10323(9) 0.90510(18) 0.14389(18) 0.0258(2) Uani 1 1 d . . . C4 C 0.06307(9) 1.0018(2) 0.2717(2) 0.0298(3) Uani 1 1 d . . . O2 O 0.38331(7) 1.22464(12) 0.28994(13) 0.02159(19) Uani 1 1 d . . . O01 O 0.37330(7) 0.56353(14) 0.17017(14) 0.0272(2) Uani 1 1 d . . . C5 C 0.11456(9) 1.1246(2) 0.37989(19) 0.0294(3) Uani 1 1 d . . . H6 H 0.2438(17) 1.236(3) 0.430(3) 0.031(6) Uiso 1 1 d . . . H3 H 0.0666(15) 0.815(3) 0.061(3) 0.033(5) Uiso 1 1 d . . . H01 H 0.3647(17) 0.453(4) 0.215(3) 0.051(7) Uiso 1 1 d . . . H5 H 0.0859(17) 1.193(3) 0.476(3) 0.043(6) Uiso 1 1 d . . . H4 H -0.0047(15) 0.984(3) 0.289(3) 0.043(6) Uiso 1 1 d . . . H12 H 0.2882(14) 0.864(3) -0.034(3) 0.033(5) Uiso 1 1 d . . . H11 H 0.1943(19) 0.773(3) -0.095(4) 0.042(7) Uiso 1 1 d . . . H02 H 0.316(2) 0.607(4) 0.112(4) 0.063(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 K1 0.02110(16) 0.01986(16) 0.01699(15) -0.00050(7) 0.00282(10) 0.00039(7) C1 0.0187(4) 0.0169(4) 0.0166(4) 0.0007(3) 0.0016(3) 0.0002(3) O1 0.0211(4) 0.0194(4) 0.0271(4) -0.0026(3) 0.0063(3) 0.0010(3) C7 0.0191(4) 0.0158(4) 0.0161(4) 0.0015(3) 0.0020(3) 0.0001(3) C6 0.0232(5) 0.0249(5) 0.0219(5) -0.0033(4) 0.0044(4) 0.0021(4) N1 0.0256(5) 0.0263(5) 0.0251(5) -0.0089(4) 0.0000(4) -0.0023(4) C2 0.0208(5) 0.0183(5) 0.0186(5) 0.0011(4) -0.0001(4) -0.0010(4) C3 0.0211(5) 0.0286(6) 0.0269(6) 0.0030(5) -0.0001(4) -0.0040(4) C4 0.0192(5) 0.0393(7) 0.0313(6) 0.0045(5) 0.0051(4) -0.0001(5) O2 0.0230(4) 0.0189(4) 0.0225(4) -0.0029(3) 0.0013(3) -0.0035(3) O01 0.0285(5) 0.0217(4) 0.0298(5) 0.0034(3) -0.0027(4) -0.0043(3) C5 0.0240(6) 0.0370(7) 0.0283(6) -0.0018(5) 0.0080(4) 0.0050(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 K1 O2 2.6982(10) 3_676 ? K1 O1 2.7127(9) 4_576 ? K1 O2 2.7547(10) 2_645 ? K1 O01 2.7550(10) . ? K1 O01 2.8756(11) 4_576 ? K1 O1 2.8964(10) . ? K1 O1 2.9042(9) 2_645 ? K1 C7 3.1332(11) 2_645 ? K1 O01 3.3601(11) 2_655 ? K1 C7 3.4599(11) . ? K1 K1 3.7162 4_575 ? K1 K1 3.7163 4_576 ? C1 C6 1.3981(16) . ? C1 C2 1.4113(15) . ? C1 C7 1.5130(15) . ? O1 C7 1.2609(14) . ? O1 K1 2.7127(9) 4_575 ? O1 K1 2.9042(9) 2_655 ? C7 O2 1.2666(14) . ? C7 K1 3.1332(11) 2_655 ? C6 C5 1.3908(18) . ? C6 H6 0.99(2) . ? N1 C2 1.3915(16) . ? N1 H12 0.92(2) . ? N1 H11 0.92(3) . ? C2 C3 1.4091(17) . ? C3 C4 1.388(2) . ? C3 H3 1.03(2) . ? C4 C5 1.395(2) . ? C4 H4 1.03(2) . ? O2 K1 2.6982(10) 3_676 ? O2 K1 2.7547(10) 2_655 ? O01 K1 2.8756(11) 4_575 ? O01 K1 3.3601(11) 2_645 ? O01 H01 0.92(3) . ? O01 H02 0.96(3) . ? C5 H5 1.02(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 K1 O1 87.54(3) 3_676 4_576 ? O2 K1 O2 86.49(3) 3_676 2_645 ? O1 K1 O2 136.52(3) 4_576 2_645 ? O2 K1 O01 152.48(3) 3_676 . ? O1 K1 O01 79.85(3) 4_576 . ? O2 K1 O01 86.08(3) 2_645 . ? O2 K1 O01 84.79(3) 3_676 4_576 ? O1 K1 O01 68.01(3) 4_576 4_576 ? O2 K1 O01 153.51(3) 2_645 4_576 ? O01 K1 O01 112.28(4) . 4_576 ? O2 K1 O1 137.80(3) 3_676 . ? O1 K1 O1 126.79(4) 4_576 . ? O2 K1 O1 82.92(3) 2_645 . ? O01 K1 O1 67.16(3) . . ? O01 K1 O1 86.88(3) 4_576 . ? O2 K1 O1 77.08(3) 3_676 2_645 ? O1 K1 O1 90.47(3) 4_576 2_645 ? O2 K1 O1 46.28(3) 2_645 2_645 ? O01 K1 O1 78.66(3) . 2_645 ? O01 K1 O1 152.49(3) 4_576 2_645 ? O1 K1 O1 120.387(15) . 2_645 ? O2 K1 C7 75.81(3) 3_676 2_645 ? O1 K1 C7 113.91(3) 4_576 2_645 ? O2 K1 C7 23.74(3) 2_645 2_645 ? O01 K1 C7 87.04(3) . 2_645 ? O01 K1 C7 160.28(3) 4_576 2_645 ? O1 K1 C7 105.08(3) . 2_645 ? O1 K1 C7 23.72(3) 2_645 2_645 ? O2 K1 O01 71.84(3) 3_676 2_655 ? O1 K1 O01 158.01(3) 4_576 2_655 ? O2 K1 O01 51.82(3) 2_645 2_655 ? O01 K1 O01 122.056(17) . 2_655 ? O01 K1 O01 101.69(3) 4_576 2_655 ? O1 K1 O01 69.55(3) . 2_655 ? O1 K1 O01 92.19(3) 2_645 2_655 ? C7 K1 O01 69.14(3) 2_645 2_655 ? O2 K1 C7 128.25(3) 3_676 . ? O1 K1 C7 116.70(3) 4_576 . ? O2 K1 C7 100.40(3) 2_645 . ? O01 K1 C7 79.19(3) . . ? O01 K1 C7 66.53(3) 4_576 . ? O1 K1 C7 20.52(2) . . ? O1 K1 C7 140.86(3) 2_645 . ? C7 K1 C7 123.71(2) 2_645 . ? O01 K1 C7 73.14(2) 2_655 . ? O2 K1 K1 132.33(2) 3_676 4_575 ? O1 K1 K1 129.30(2) 4_576 4_575 ? O2 K1 K1 46.40(2) 2_645 4_575 ? O01 K1 K1 50.11(2) . 4_575 ? O01 K1 K1 132.71(2) 4_576 4_575 ? O1 K1 K1 46.417(18) . 4_575 ? O1 K1 K1 74.08(2) 2_645 4_575 ? C7 K1 K1 62.69(2) 2_645 4_575 ? O01 K1 K1 72.220(19) 2_655 4_575 ? C7 K1 K1 66.940(19) . 4_575 ? O2 K1 K1 47.68(2) 3_676 4_576 ? O1 K1 K1 50.66(2) 4_576 4_576 ? O2 K1 K1 133.59(2) 2_645 4_576 ? O01 K1 K1 129.86(2) . 4_576 ? O01 K1 K1 47.32(2) 4_576 4_576 ? O1 K1 K1 133.62(2) . 4_576 ? O1 K1 K1 105.89(2) 2_645 4_576 ? C7 K1 K1 117.29(2) 2_645 4_576 ? O01 K1 K1 107.812(19) 2_655 4_576 ? C7 K1 K1 113.09(2) . 4_576 ? K1 K1 K1 179.957(16) 4_575 4_576 ? C6 C1 C2 118.84(10) . . ? C6 C1 C7 117.78(10) . . ? C2 C1 C7 123.37(10) . . ? C7 O1 K1 171.20(8) . 4_575 ? C7 O1 K1 105.83(7) . . ? K1 O1 K1 82.92(2) 4_575 . ? C7 O1 K1 88.38(7) . 2_655 ? K1 O1 K1 89.53(3) 4_575 2_655 ? K1 O1 K1 110.10(3) . 2_655 ? O1 C7 O2 123.68(11) . . ? O1 C7 C1 119.06(10) . . ? O2 C7 C1 117.25(10) . . ? O1 C7 K1 67.90(6) . 2_655 ? O2 C7 K1 61.12(6) . 2_655 ? C1 C7 K1 156.08(7) . 2_655 ? O1 C7 K1 53.65(6) . . ? O2 C7 K1 105.13(7) . . ? C1 C7 K1 110.44(6) . . ? K1 C7 K1 92.16(3) 2_655 . ? C5 C6 C1 122.22(12) . . ? C5 C6 H6 120.2(14) . . ? C1 C6 H6 117.6(14) . . ? C2 N1 H12 112.7(13) . . ? C2 N1 H11 117.0(17) . . ? H12 N1 H11 116(2) . . ? N1 C2 C3 118.72(11) . . ? N1 C2 C1 122.51(11) . . ? C3 C2 C1 118.74(11) . . ? C4 C3 C2 121.19(12) . . ? C4 C3 H3 121.9(12) . . ? C2 C3 H3 116.9(12) . . ? C3 C4 C5 120.24(12) . . ? C3 C4 H4 121.1(12) . . ? C5 C4 H4 118.7(12) . . ? C7 O2 K1 126.43(8) . 3_676 ? C7 O2 K1 95.14(7) . 2_655 ? K1 O2 K1 85.92(3) 3_676 2_655 ? K1 O01 K1 82.57(3) . 4_575 ? K1 O01 K1 101.60(3) . 2_645 ? K1 O01 K1 78.31(3) 4_575 2_645 ? K1 O01 H01 107.8(16) . . ? K1 O01 H01 141.5(16) 4_575 . ? K1 O01 H01 63.4(16) 2_645 . ? K1 O01 H02 122.6(17) . . ? K1 O01 H02 94.0(17) 4_575 . ? K1 O01 H02 133.9(17) 2_645 . ? H01 O01 H02 109(2) . . ? C6 C5 C4 118.75(12) . . ? C6 C5 H5 120.7(14) . . ? C4 C5 H5 120.5(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 K1 O1 C7 -71.52(8) 3_676 . . . ? O1 K1 O1 C7 66.61(7) 4_576 . . . ? O2 K1 O1 C7 -148.29(8) 2_645 . . . ? O01 K1 O1 C7 122.99(8) . . . . ? O01 K1 O1 C7 7.21(7) 4_576 . . . ? O1 K1 O1 C7 -176.63(7) 2_645 . . . ? C7 K1 O1 C7 -156.88(7) 2_645 . . . ? O01 K1 O1 C7 -96.50(7) 2_655 . . . ? K1 K1 O1 C7 178.95(8) 4_575 . . . ? K1 K1 O1 C7 -1.01(8) 4_576 . . . ? O2 K1 O1 K1 109.53(4) 3_676 . . 4_575 ? O1 K1 O1 K1 -112.34(4) 4_576 . . 4_575 ? O2 K1 O1 K1 32.75(3) 2_645 . . 4_575 ? O01 K1 O1 K1 -55.96(3) . . . 4_575 ? O01 K1 O1 K1 -171.74(3) 4_576 . . 4_575 ? O1 K1 O1 K1 4.42(3) 2_645 . . 4_575 ? C7 K1 O1 K1 24.17(3) 2_645 . . 4_575 ? O01 K1 O1 K1 84.55(3) 2_655 . . 4_575 ? C7 K1 O1 K1 -178.95(8) . . . 4_575 ? K1 K1 O1 K1 -179.964(11) 4_576 . . 4_575 ? O2 K1 O1 K1 22.64(6) 3_676 . . 2_655 ? O1 K1 O1 K1 160.76(3) 4_576 . . 2_655 ? O2 K1 O1 K1 -54.14(3) 2_645 . . 2_655 ? O01 K1 O1 K1 -142.85(4) . . . 2_655 ? O01 K1 O1 K1 101.36(3) 4_576 . . 2_655 ? O1 K1 O1 K1 -82.48(4) 2_645 . . 2_655 ? C7 K1 O1 K1 -62.73(4) 2_645 . . 2_655 ? O01 K1 O1 K1 -2.34(3) 2_655 . . 2_655 ? C7 K1 O1 K1 94.15(8) . . . 2_655 ? K1 K1 O1 K1 -86.89(3) 4_575 . . 2_655 ? K1 K1 O1 K1 93.14(3) 4_576 . . 2_655 ? K1 O1 C7 O2 -102.6(5) 4_575 . . . ? K1 O1 C7 O2 84.21(11) . . . . ? K1 O1 C7 O2 -26.24(11) 2_655 . . . ? K1 O1 C7 C1 78.2(5) 4_575 . . . ? K1 O1 C7 C1 -95.00(9) . . . . ? K1 O1 C7 C1 154.56(9) 2_655 . . . ? K1 O1 C7 K1 -76.4(5) 4_575 . . 2_655 ? K1 O1 C7 K1 110.44(4) . . . 2_655 ? K1 O1 C7 K1 173.2(5) 4_575 . . . ? K1 O1 C7 K1 -110.44(4) 2_655 . . . ? C6 C1 C7 O1 162.08(11) . . . . ? C2 C1 C7 O1 -17.15(16) . . . . ? C6 C1 C7 O2 -17.17(15) . . . . ? C2 C1 C7 O2 163.60(11) . . . . ? C6 C1 C7 K1 -96.89(19) . . . 2_655 ? C2 C1 C7 K1 83.9(2) . . . 2_655 ? C6 C1 C7 K1 103.18(10) . . . . ? C2 C1 C7 K1 -76.05(11) . . . . ? O2 K1 C7 O1 125.78(7) 3_676 . . . ? O1 K1 C7 O1 -124.64(7) 4_576 . . . ? O2 K1 C7 O1 32.02(8) 2_645 . . . ? O01 K1 C7 O1 -51.90(7) . . . . ? O01 K1 C7 O1 -172.15(8) 4_576 . . . ? O1 K1 C7 O1 4.61(9) 2_645 . . . ? C7 K1 C7 O1 27.11(8) 2_645 . . . ? O01 K1 C7 O1 76.60(7) 2_655 . . . ? K1 K1 C7 O1 -0.82(7) 4_575 . . . ? K1 K1 C7 O1 179.20(7) 4_576 . . . ? O2 K1 C7 O2 4.83(10) 3_676 . . . ? O1 K1 C7 O2 114.42(8) 4_576 . . . ? O2 K1 C7 O2 -88.92(8) 2_645 . . . ? O01 K1 C7 O2 -172.85(8) . . . . ? O01 K1 C7 O2 66.91(8) 4_576 . . . ? O1 K1 C7 O2 -120.95(11) . . . . ? O1 K1 C7 O2 -116.34(8) 2_645 . . . ? C7 K1 C7 O2 -93.83(8) 2_645 . . . ? O01 K1 C7 O2 -44.35(7) 2_655 . . . ? K1 K1 C7 O2 -121.77(8) 4_575 . . . ? K1 K1 C7 O2 58.26(8) 4_576 . . . ? O2 K1 C7 C1 -122.54(7) 3_676 . . . ? O1 K1 C7 C1 -12.96(8) 4_576 . . . ? O2 K1 C7 C1 143.70(7) 2_645 . . . ? O01 K1 C7 C1 59.78(7) . . . . ? O01 K1 C7 C1 -60.47(7) 4_576 . . . ? O1 K1 C7 C1 111.68(11) . . . . ? O1 K1 C7 C1 116.28(7) 2_645 . . . ? C7 K1 C7 C1 138.79(7) 2_645 . . . ? O01 K1 C7 C1 -171.72(7) 2_655 . . . ? K1 K1 C7 C1 110.85(7) 4_575 . . . ? K1 K1 C7 C1 -69.12(7) 4_576 . . . ? O2 K1 C7 K1 65.46(4) 3_676 . . 2_655 ? O1 K1 C7 K1 175.05(3) 4_576 . . 2_655 ? O2 K1 C7 K1 -28.29(3) 2_645 . . 2_655 ? O01 K1 C7 K1 -112.22(3) . . . 2_655 ? O01 K1 C7 K1 127.53(4) 4_576 . . 2_655 ? O1 K1 C7 K1 -60.32(7) . . . 2_655 ? O1 K1 C7 K1 -55.71(5) 2_645 . . 2_655 ? C7 K1 C7 K1 -33.21(4) 2_645 . . 2_655 ? O01 K1 C7 K1 16.28(2) 2_655 . . 2_655 ? K1 K1 C7 K1 -61.14(2) 4_575 . . 2_655 ? K1 K1 C7 K1 118.885(19) 4_576 . . 2_655 ? C2 C1 C6 C5 1.00(19) . . . . ? C7 C1 C6 C5 -178.27(12) . . . . ? C6 C1 C2 N1 -177.82(11) . . . . ? C7 C1 C2 N1 1.40(18) . . . . ? C6 C1 C2 C3 0.25(17) . . . . ? C7 C1 C2 C3 179.47(10) . . . . ? N1 C2 C3 C4 176.99(12) . . . . ? C1 C2 C3 C4 -1.15(19) . . . . ? C2 C3 C4 C5 0.8(2) . . . . ? O1 C7 O2 K1 -60.82(15) . . . 3_676 ? C1 C7 O2 K1 118.40(9) . . . 3_676 ? K1 C7 O2 K1 -88.71(8) 2_655 . . 3_676 ? K1 C7 O2 K1 -4.72(10) . . . 3_676 ? O1 C7 O2 K1 27.89(12) . . . 2_655 ? C1 C7 O2 K1 -152.89(8) . . . 2_655 ? K1 C7 O2 K1 84.00(4) . . . 2_655 ? O2 K1 O01 K1 -107.16(6) 3_676 . . 4_575 ? O1 K1 O01 K1 -171.18(3) 4_576 . . 4_575 ? O2 K1 O01 K1 -32.49(3) 2_645 . . 4_575 ? O01 K1 O01 K1 127.80(4) 4_576 . . 4_575 ? O1 K1 O01 K1 51.47(2) . . . 4_575 ? O1 K1 O01 K1 -78.64(3) 2_645 . . 4_575 ? C7 K1 O01 K1 -56.25(3) 2_645 . . 4_575 ? O01 K1 O01 K1 6.80(4) 2_655 . . 4_575 ? C7 K1 O01 K1 68.89(3) . . . 4_575 ? K1 K1 O01 K1 -179.958(13) 4_576 . . 4_575 ? O2 K1 O01 K1 -30.78(8) 3_676 . . 2_645 ? O1 K1 O01 K1 -94.80(3) 4_576 . . 2_645 ? O2 K1 O01 K1 43.90(3) 2_645 . . 2_645 ? O01 K1 O01 K1 -155.82(3) 4_576 . . 2_645 ? O1 K1 O01 K1 127.85(4) . . . 2_645 ? O1 K1 O01 K1 -2.26(2) 2_645 . . 2_645 ? C7 K1 O01 K1 20.13(3) 2_645 . . 2_645 ? O01 K1 O01 K1 83.18(4) 2_655 . . 2_645 ? C7 K1 O01 K1 145.28(3) . . . 2_645 ? K1 K1 O01 K1 76.38(3) 4_575 . . 2_645 ? K1 K1 O01 K1 -103.57(3) 4_576 . . 2_645 ? C1 C6 C5 C4 -1.3(2) . . . . ? C3 C4 C5 C6 0.4(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O01 H01 O2 0.92(3) 1.83(3) 2.7269(14) 163(2) 1_545 N1 H12 O1 0.92(2) 2.09(2) 2.7348(14) 125.5(17) . O01 H02 N1 0.96(3) 2.13(3) 3.0016(16) 150(2) . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 31.92 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.314 _refine_diff_density_min -0.729 _refine_diff_density_rms 0.096