Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'Schmidbaur, Hubert' 'Wiesbrock, Frank' _publ_contact_author_name 'Prof Hubert Schmidbaur' _publ_contact_author_address ; Anorganisch-chemisches Institut der Technischen Universitat Munchen Lichtenbergstrasse 4 D-85747 Garching GERMANY ; _publ_contact_author_email 'H.SCHMIDBAUR@1RZ.TUM.DE' _publ_section_title ; Zinc and Lithium Hydrogen-beta-glutamate: Large-Pore Network Layer Structures ; data_wies6 _database_code_CSD 186989 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H22 N2 O11 Zn' _chemical_formula_weight 411.67 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' 'Zn' 'Zn' 0.2839 1.4301 '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 8.85100(10) _cell_length_b 9.10500(10) _cell_length_c 19.8280(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.3830(6) _cell_angle_gamma 90.00 _cell_volume 1584.66(4) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 42910 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.726 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 1.612 _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 42910 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 27.19 _reflns_number_total 3514 _reflns_number_gt 3268 _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^)+(0.0501P)^2^+1.2647P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment isotropic _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3514 _refine_ls_number_parameters 305 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0380 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0934 _refine_ls_wR_factor_gt 0.0911 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 Zn1 Zn 0.38248(2) 0.24800(2) 0.133592(12) 0.01734(10) Uani 1 1 d . . . O14 O 0.17567(16) 0.16756(15) 0.09971(7) 0.0213(3) Uani 1 1 d . . . C5 C 0.1011(2) 0.24427(19) 0.05203(11) 0.0176(4) Uani 1 1 d . . . O13 O 0.14968(17) 0.35912(15) 0.02953(8) 0.0240(3) Uani 1 1 d . . . C4 C -0.0550(2) 0.1881(2) 0.02325(11) 0.0200(4) Uani 1 1 d . . . N1 N -0.1136(2) 0.35063(19) -0.07632(9) 0.0184(3) Uani 1 1 d . . . C3 C -0.1585(2) 0.3101(2) -0.00833(10) 0.0187(4) Uani 1 1 d . . . O3 O -0.1224(2) 0.10466(18) -0.15454(9) 0.0286(3) Uani 1 1 d . . . O2 O 0.2939(2) 0.1018(2) -0.06296(9) 0.0324(4) Uani 1 1 d . . . O1 O 0.7923(2) 0.6342(2) 0.12699(9) 0.0374(4) Uani 1 1 d . . . H31 H -0.144(3) 0.396(3) 0.0206(12) 0.016(5) Uiso 1 1 d . . . H03 H -0.011(3) 0.378(3) -0.0722(13) 0.028(7) Uiso 1 1 d . . . H42 H -0.100(3) 0.137(3) 0.0562(14) 0.031(7) Uiso 1 1 d . . . H41 H -0.044(3) 0.119(3) -0.0107(14) 0.027(6) Uiso 1 1 d . . . H02 H -0.119(3) 0.270(3) -0.1023(16) 0.031(7) Uiso 1 1 d . . . H01 H -0.168(3) 0.429(3) -0.0935(15) 0.035(7) Uiso 1 1 d . . . H6 H -0.054(4) 0.102(4) -0.1803(18) 0.050(9) Uiso 1 1 d . . . H2 H 0.756(4) 0.708(4) 0.1013(19) 0.054(9) Uiso 1 1 d . . . H4 H 0.344(4) 0.054(3) -0.0902(17) 0.040(8) Uiso 1 1 d . . . H3 H 0.357(4) 0.127(4) -0.0299(18) 0.053(10) Uiso 1 1 d . . . H5 H -0.129(4) 0.021(4) -0.1385(16) 0.043(8) Uiso 1 1 d . . . H1 H 0.733(5) 0.560(5) 0.108(2) 0.077(13) Uiso 1 1 d . . . O12 O -0.51576(17) 0.20601(18) 0.05295(8) 0.0260(3) Uani 1 1 d . . . O11 O -0.31715(17) 0.33272(18) 0.10177(7) 0.0274(3) Uani 1 1 d . . . C2 C -0.3259(3) 0.2679(2) -0.01605(11) 0.0209(4) Uani 1 1 d . . . H22 H -0.383(3) 0.341(3) -0.0456(14) 0.030(7) Uiso 1 1 d . . . H21 H -0.343(3) 0.166(3) -0.0375(13) 0.026(6) Uiso 1 1 d . . . C1 C -0.3880(2) 0.2696(2) 0.05185(11) 0.0202(4) Uani 1 1 d . . . O16 O 0.36618(16) 0.46021(15) 0.15161(7) 0.0211(3) Uani 1 1 d . . . C8 C 0.5272(3) 0.7531(2) 0.26933(11) 0.0203(4) Uani 1 1 d . . . N2 N 0.6937(2) 0.7449(2) 0.26300(11) 0.0239(4) Uani 1 1 d . . . H81 H 0.515(3) 0.693(3) 0.3125(13) 0.024(6) Uiso 1 1 d . . . H06 H 0.713(4) 0.809(4) 0.2310(17) 0.042(8) Uiso 1 1 d . . . H05 H 0.716(4) 0.656(4) 0.2580(17) 0.050(9) Uiso 1 1 d . . . H04 H 0.747(4) 0.772(3) 0.3036(18) 0.042(9) Uiso 1 1 d . . . O15 O 0.55763(17) 0.45422(16) 0.23709(7) 0.0232(3) Uani 1 1 d . . . C6 C 0.4579(2) 0.5205(2) 0.19952(9) 0.0174(4) Uani 1 1 d . . . C7 C 0.4325(2) 0.6835(2) 0.20821(11) 0.0223(4) Uani 1 1 d . . . H72 H 0.327(4) 0.698(4) 0.2118(15) 0.040(8) Uiso 1 1 d . . . H71 H 0.456(4) 0.735(3) 0.1661(18) 0.041(9) Uiso 1 1 d . . . O18 O 0.40792(18) 1.12763(16) 0.21657(8) 0.0272(3) Uani 1 1 d . . . C10 C 0.4950(2) 1.0163(2) 0.22110(10) 0.0215(4) Uani 1 1 d . . . O17 O 0.59466(19) 0.99177(19) 0.18383(8) 0.0330(4) Uani 1 1 d . . . C9 C 0.4791(2) 0.9122(2) 0.27974(10) 0.0217(4) Uani 1 1 d . . . H92 H 0.542(3) 0.952(3) 0.3202(14) 0.034(7) Uiso 1 1 d . . . H91 H 0.370(3) 0.915(3) 0.2892(14) 0.034(7) 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 Zn1 0.01712(15) 0.01514(16) 0.01969(15) -0.00031(7) 0.00212(10) -0.00009(8) O14 0.0205(7) 0.0204(7) 0.0219(7) 0.0042(5) -0.0014(5) -0.0012(6) C5 0.0205(10) 0.0160(9) 0.0171(9) -0.0010(6) 0.0049(8) 0.0015(7) O13 0.0238(7) 0.0174(7) 0.0301(8) 0.0040(6) 0.0008(6) -0.0026(6) C4 0.0200(9) 0.0162(9) 0.0231(9) 0.0034(8) 0.0005(7) -0.0004(8) N1 0.0204(8) 0.0154(8) 0.0197(8) 0.0007(6) 0.0034(6) 0.0007(7) C3 0.0210(9) 0.0169(9) 0.0180(9) 0.0014(7) 0.0023(7) 0.0001(8) O3 0.0381(9) 0.0192(8) 0.0304(8) -0.0017(6) 0.0116(7) -0.0019(7) O2 0.0306(9) 0.0354(9) 0.0307(9) -0.0062(7) 0.0020(7) 0.0022(7) O1 0.0429(10) 0.0334(9) 0.0340(9) 0.0032(8) -0.0025(8) 0.0026(8) O12 0.0218(7) 0.0310(8) 0.0260(8) -0.0026(7) 0.0063(6) -0.0028(7) O11 0.0284(8) 0.0328(8) 0.0208(7) -0.0019(6) 0.0028(6) -0.0041(7) C2 0.0196(10) 0.0244(10) 0.0182(10) 0.0003(8) 0.0006(8) 0.0004(8) C1 0.0203(10) 0.0211(9) 0.0190(10) 0.0023(7) 0.0011(8) 0.0036(7) O16 0.0219(7) 0.0169(6) 0.0233(7) -0.0014(5) -0.0019(5) -0.0019(5) C8 0.0206(10) 0.0181(10) 0.0217(10) -0.0001(7) 0.0007(8) -0.0002(7) N2 0.0196(9) 0.0237(11) 0.0276(10) -0.0033(7) -0.0007(8) -0.0002(7) O15 0.0240(7) 0.0203(7) 0.0239(7) 0.0004(6) -0.0025(6) 0.0022(6) C6 0.0160(8) 0.0174(9) 0.0187(9) 0.0001(7) 0.0019(7) -0.0020(7) C7 0.0206(10) 0.0185(10) 0.0261(10) -0.0027(8) -0.0038(8) 0.0005(8) O18 0.0322(8) 0.0223(7) 0.0263(8) 0.0024(6) 0.0006(6) 0.0060(6) C10 0.0195(9) 0.0193(9) 0.0247(10) -0.0012(8) -0.0006(7) -0.0033(8) O17 0.0333(9) 0.0341(9) 0.0339(9) 0.0101(7) 0.0133(7) 0.0062(7) C9 0.0252(10) 0.0175(9) 0.0215(9) -0.0014(7) -0.0005(8) 0.0009(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O18 1.9656(15) 1_545 ? Zn1 O12 1.9708(15) 1_655 ? Zn1 O16 1.9736(14) . ? Zn1 O14 2.0055(14) . ? O14 C5 1.287(2) . ? C5 O13 1.236(2) . ? C5 C4 1.514(3) . ? C4 C3 1.523(3) . ? C4 H42 0.93(3) . ? C4 H41 0.93(3) . ? N1 C3 1.500(2) . ? N1 H03 0.94(3) . ? N1 H02 0.90(3) . ? N1 H01 0.90(3) . ? C3 C2 1.520(3) . ? C3 H31 0.97(2) . ? O3 H6 0.84(4) . ? O3 H5 0.83(3) . ? O2 H4 0.86(3) . ? O2 H3 0.84(4) . ? O1 H2 0.88(4) . ? O1 H1 0.91(5) . ? O12 C1 1.273(3) . ? O12 Zn1 1.9708(15) 1_455 ? O11 C1 1.242(3) . ? C2 C1 1.518(3) . ? C2 H22 0.98(3) . ? C2 H21 1.02(3) . ? O16 C6 1.290(2) . ? C8 N2 1.497(3) . ? C8 C7 1.521(3) . ? C8 C9 1.531(3) . ? C8 H81 1.03(3) . ? N2 H06 0.89(3) . ? N2 H05 0.85(4) . ? N2 H04 0.91(4) . ? O15 C6 1.236(2) . ? C6 C7 1.515(3) . ? C7 H72 0.96(3) . ? C7 H71 1.00(3) . ? O18 C10 1.269(3) . ? O18 Zn1 1.9656(15) 1_565 ? C10 O17 1.242(3) . ? C10 C9 1.521(3) . ? C9 H92 0.98(3) . ? C9 H91 1.01(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 O18 Zn1 O12 123.77(7) 1_545 1_655 ? O18 Zn1 O16 113.42(6) 1_545 . ? O12 Zn1 O16 112.86(7) 1_655 . ? O18 Zn1 O14 94.49(6) 1_545 . ? O12 Zn1 O14 98.63(6) 1_655 . ? O16 Zn1 O14 109.47(6) . . ? C5 O14 Zn1 114.06(12) . . ? O13 C5 O14 123.71(19) . . ? O13 C5 C4 119.52(18) . . ? O14 C5 C4 116.77(16) . . ? C5 C4 C3 112.34(16) . . ? C5 C4 H42 110.8(17) . . ? C3 C4 H42 111.4(17) . . ? C5 C4 H41 108.7(16) . . ? C3 C4 H41 108.0(16) . . ? H42 C4 H41 105(2) . . ? C3 N1 H03 110.7(16) . . ? C3 N1 H02 108.2(19) . . ? H03 N1 H02 105(2) . . ? C3 N1 H01 110.0(18) . . ? H03 N1 H01 107(2) . . ? H02 N1 H01 116(3) . . ? N1 C3 C2 109.84(16) . . ? N1 C3 C4 109.53(16) . . ? C2 C3 C4 112.59(16) . . ? N1 C3 H31 107.5(14) . . ? C2 C3 H31 108.7(14) . . ? C4 C3 H31 108.6(14) . . ? H6 O3 H5 107(3) . . ? H4 O2 H3 106(3) . . ? H2 O1 H1 100(3) . . ? C1 O12 Zn1 115.16(14) . 1_455 ? C1 C2 C3 111.56(17) . . ? C1 C2 H22 107.7(16) . . ? C3 C2 H22 107.8(16) . . ? C1 C2 H21 109.3(15) . . ? C3 C2 H21 111.0(15) . . ? H22 C2 H21 109(2) . . ? O11 C1 O12 123.7(2) . . ? O11 C1 C2 120.53(19) . . ? O12 C1 C2 115.72(18) . . ? C6 O16 Zn1 119.72(12) . . ? N2 C8 C7 111.10(18) . . ? N2 C8 C9 110.62(16) . . ? C7 C8 C9 111.57(17) . . ? N2 C8 H81 104.6(14) . . ? C7 C8 H81 109.6(14) . . ? C9 C8 H81 109.1(15) . . ? C8 N2 H06 108(2) . . ? C8 N2 H05 108(2) . . ? H06 N2 H05 118(3) . . ? C8 N2 H04 108(2) . . ? H06 N2 H04 109(3) . . ? H05 N2 H04 105(3) . . ? O15 C6 O16 124.70(18) . . ? O15 C6 C7 120.97(17) . . ? O16 C6 C7 114.31(16) . . ? C6 C7 C8 115.11(17) . . ? C6 C7 H72 108(2) . . ? C8 C7 H72 109.1(19) . . ? C6 C7 H71 108.1(17) . . ? C8 C7 H71 108.5(18) . . ? H72 C7 H71 108(3) . . ? C10 O18 Zn1 120.50(14) . 1_565 ? O17 C10 O18 125.0(2) . . ? O17 C10 C9 119.02(19) . . ? O18 C10 C9 115.91(18) . . ? C10 C9 C8 115.61(17) . . ? C10 C9 H92 107.1(16) . . ? C8 C9 H92 108.7(16) . . ? C10 C9 H91 108.0(16) . . ? C8 C9 H91 110.0(16) . . ? H92 C9 H91 107(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O18 Zn1 O14 C5 164.74(13) 1_545 . . . ? O12 Zn1 O14 C5 -70.11(14) 1_655 . . . ? O16 Zn1 O14 C5 47.95(14) . . . . ? Zn1 O14 C5 O13 -1.4(2) . . . . ? Zn1 O14 C5 C4 178.95(13) . . . . ? O13 C5 C4 C3 -24.1(3) . . . . ? O14 C5 C4 C3 155.49(17) . . . . ? C5 C4 C3 N1 76.4(2) . . . . ? C5 C4 C3 C2 -161.13(17) . . . . ? N1 C3 C2 C1 -163.28(16) . . . . ? C4 C3 C2 C1 74.4(2) . . . . ? Zn1 O12 C1 O11 12.2(3) 1_455 . . . ? Zn1 O12 C1 C2 -166.28(14) 1_455 . . . ? C3 C2 C1 O11 16.0(3) . . . . ? C3 C2 C1 O12 -165.39(18) . . . . ? O18 Zn1 O16 C6 44.34(15) 1_545 . . . ? O12 Zn1 O16 C6 -102.80(14) 1_655 . . . ? O14 Zn1 O16 C6 148.44(13) . . . . ? Zn1 O16 C6 O15 -1.0(3) . . . . ? Zn1 O16 C6 C7 -179.65(13) . . . . ? O15 C6 C7 C8 -5.3(3) . . . . ? O16 C6 C7 C8 173.41(17) . . . . ? N2 C8 C7 C6 63.7(2) . . . . ? C9 C8 C7 C6 -172.31(17) . . . . ? Zn1 O18 C10 O17 17.1(3) 1_565 . . . ? Zn1 O18 C10 C9 -166.61(13) 1_565 . . . ? O17 C10 C9 C8 -28.8(3) . . . . ? O18 C10 C9 C8 154.73(18) . . . . ? N2 C8 C9 C10 63.7(2) . . . . ? C7 C8 C9 C10 -60.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.19 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.922 _refine_diff_density_min -0.561 _refine_diff_density_rms 0.077 data_wies9 _database_code_CSD 186990 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H10 Li N O5' _chemical_formula_weight 171.08 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 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 7.3350(2) _cell_length_b 10.3040(2) _cell_length_c 9.7550(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.1410(10) _cell_angle_gamma 90.00 _cell_volume 731.56(3) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 18561 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.136 _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 18561 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.43 _diffrn_reflns_theta_max 27.22 _reflns_number_total 1619 _reflns_number_gt 1511 _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^)+(0.0497P)^2^+0.2911P] 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 1619 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0359 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0909 _refine_ls_wR_factor_gt 0.0891 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 O2 O 0.35005(11) 0.80296(8) 0.08110(9) 0.0185(2) Uani 1 1 d . . . O4 O -0.29777(11) 0.84565(8) 0.58278(8) 0.0169(2) Uani 1 1 d . . . O3 O -0.29973(12) 1.00003(8) 0.42156(9) 0.0220(2) Uani 1 1 d . . . O1 O 0.18156(11) 0.98291(8) 0.08887(8) 0.0167(2) Uani 1 1 d . . . N1 N -0.17407(13) 0.89883(9) 0.17516(10) 0.0141(2) Uani 1 1 d . . . C2 C 0.14041(15) 0.81314(11) 0.24859(11) 0.0151(2) Uani 1 1 d . . . C1 C 0.22973(14) 0.87093(11) 0.12958(11) 0.0137(2) Uani 1 1 d . . . C4 C -0.09014(15) 0.82427(11) 0.41528(11) 0.0153(2) Uani 1 1 d . . . C3 C -0.02086(15) 0.88907(10) 0.29190(11) 0.0133(2) Uani 1 1 d . . . C5 C -0.24213(15) 0.89628(11) 0.47689(11) 0.0138(2) Uani 1 1 d . . . Li1 Li -0.4599(3) 1.13722(19) 0.3592(2) 0.0170(4) Uani 1 1 d . . . H31 H 0.018(2) 0.9773(14) 0.3157(15) 0.014(3) Uiso 1 1 d . . . H41 H -0.133(2) 0.7342(17) 0.3916(16) 0.027(4) Uiso 1 1 d . . . H21 H 0.233(2) 0.8097(16) 0.3302(17) 0.026(4) Uiso 1 1 d . . . H42 H 0.014(2) 0.8174(15) 0.4869(17) 0.023(4) Uiso 1 1 d . . . H3 H -0.269(2) 0.9442(16) 0.2047(16) 0.021(4) Uiso 1 1 d . . . H2 H -0.142(2) 0.9435(17) 0.1012(18) 0.028(4) Uiso 1 1 d . . . H22 H 0.105(2) 0.7220(17) 0.2266(17) 0.026(4) Uiso 1 1 d . . . H1 H -0.219(2) 0.8158(18) 0.1461(18) 0.031(4) Uiso 1 1 d . . . O01 O -0.48528(13) 1.11085(9) 0.15600(9) 0.0214(2) Uani 1 1 d . . . H02 H -0.585(3) 1.0704(19) 0.1274(19) 0.040(5) Uiso 1 1 d . . . H01 H -0.437(3) 1.142(2) 0.080(2) 0.053(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 O2 0.0188(4) 0.0185(4) 0.0200(4) 0.0018(3) 0.0093(3) 0.0032(3) O4 0.0165(4) 0.0192(4) 0.0161(4) 0.0034(3) 0.0063(3) 0.0015(3) O3 0.0247(5) 0.0209(4) 0.0220(4) 0.0071(3) 0.0086(3) 0.0094(3) O1 0.0158(4) 0.0164(4) 0.0182(4) 0.0038(3) 0.0030(3) 0.0009(3) N1 0.0136(5) 0.0156(5) 0.0132(4) 0.0005(4) 0.0023(3) 0.0007(4) C2 0.0151(5) 0.0159(5) 0.0150(5) 0.0020(4) 0.0048(4) 0.0019(4) C1 0.0116(5) 0.0162(5) 0.0132(5) -0.0003(4) 0.0010(4) -0.0013(4) C4 0.0156(5) 0.0163(5) 0.0145(5) 0.0026(4) 0.0046(4) 0.0025(4) C3 0.0128(5) 0.0143(5) 0.0128(5) 0.0002(4) 0.0020(4) 0.0004(4) C5 0.0128(5) 0.0153(5) 0.0133(5) 0.0002(4) 0.0020(4) -0.0007(4) Li1 0.0173(9) 0.0163(9) 0.0180(9) 0.0008(7) 0.0045(7) 0.0008(7) O01 0.0203(4) 0.0285(5) 0.0156(4) 0.0008(3) 0.0028(3) -0.0088(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 O2 C1 1.2636(14) . ? O2 Li1 1.946(2) 2_545 ? O4 C5 1.2691(14) . ? O4 Li1 1.940(2) 3_476 ? O3 C5 1.2474(14) . ? O3 Li1 1.890(2) . ? O1 C1 1.2566(14) . ? N1 C3 1.5006(14) . ? N1 H3 0.912(17) . ? N1 H2 0.911(18) . ? N1 H1 0.947(18) . ? C2 C3 1.5212(15) . ? C2 C1 1.5234(15) . ? C2 H21 0.981(17) . ? C2 H22 0.990(17) . ? C4 C3 1.5181(15) . ? C4 C5 1.5235(15) . ? C4 H41 0.997(17) . ? C4 H42 0.973(17) . ? C3 H31 0.972(15) . ? Li1 O4 1.940(2) 3_476 ? Li1 O2 1.946(2) 2 ? Li1 O01 1.987(2) . ? O01 H02 0.86(2) . ? O01 H01 0.92(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 C1 O2 Li1 131.05(9) . 2_545 ? C5 O4 Li1 126.81(9) . 3_476 ? C5 O3 Li1 160.74(10) . . ? C3 N1 H3 108.8(10) . . ? C3 N1 H2 113.1(10) . . ? H3 N1 H2 105.8(15) . . ? C3 N1 H1 111.5(11) . . ? H3 N1 H1 107.9(14) . . ? H2 N1 H1 109.5(15) . . ? C3 C2 C1 115.69(9) . . ? C3 C2 H21 106.1(9) . . ? C1 C2 H21 108.2(10) . . ? C3 C2 H22 110.9(9) . . ? C1 C2 H22 109.3(9) . . ? H21 C2 H22 106.1(13) . . ? O1 C1 O2 124.94(10) . . ? O1 C1 C2 117.97(9) . . ? O2 C1 C2 117.07(10) . . ? C3 C4 C5 115.60(9) . . ? C3 C4 H41 110.6(9) . . ? C5 C4 H41 108.8(9) . . ? C3 C4 H42 106.9(9) . . ? C5 C4 H42 107.5(9) . . ? H41 C4 H42 107.1(13) . . ? N1 C3 C4 109.77(9) . . ? N1 C3 C2 111.01(9) . . ? C4 C3 C2 110.03(9) . . ? N1 C3 H31 106.7(8) . . ? C4 C3 H31 109.8(8) . . ? C2 C3 H31 109.5(9) . . ? O3 C5 O4 125.35(10) . . ? O3 C5 C4 118.15(10) . . ? O4 C5 C4 116.49(9) . . ? O3 Li1 O4 121.99(11) . 3_476 ? O3 Li1 O2 110.04(10) . 2 ? O4 Li1 O2 101.14(10) 3_476 2 ? O3 Li1 O01 101.32(10) . . ? O4 Li1 O01 109.14(10) 3_476 . ? O2 Li1 O01 113.74(10) 2 . ? Li1 O01 H02 111.2(13) . . ? Li1 O01 H01 139.2(14) . . ? H02 O01 H01 108.0(19) . . ? 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 O2 C1 O1 173.18(11) 2_545 . . . ? Li1 O2 C1 C2 -5.30(17) 2_545 . . . ? C3 C2 C1 O1 9.17(15) . . . . ? C3 C2 C1 O2 -172.24(9) . . . . ? C5 C4 C3 N1 -62.26(12) . . . . ? C5 C4 C3 C2 175.30(9) . . . . ? C1 C2 C3 N1 61.02(12) . . . . ? C1 C2 C3 C4 -177.27(9) . . . . ? Li1 O3 C5 O4 -32.6(4) . . . . ? Li1 O3 C5 C4 148.5(3) . . . . ? Li1 O4 C5 O3 28.85(18) 3_476 . . . ? Li1 O4 C5 C4 -152.29(11) 3_476 . . . ? C3 C4 C5 O3 1.10(15) . . . . ? C3 C4 C5 O4 -177.85(10) . . . . ? C5 O3 Li1 O4 10.7(4) . . . 3_476 ? C5 O3 Li1 O2 128.7(3) . . . 2 ? C5 O3 Li1 O01 -110.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.22 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.249 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.053