Supplementary Material for CrystEngComm This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Hubert Schmidbaur' 'Frank Wiesbrock' _publ_contact_author_name 'Prof Hubert Schmidbaur' _publ_contact_author_address ; Anorganisch-chemisches Institut Technische Universitaet Muenchen Lichtenbergstrasse 4 Garching 85747 GERMANY ; _publ_contact_author_email H.SCHMIDBAUR@LRZ.TUM.DE _publ_section_title ; Lithium L-Hydrogen-alpha-glutamate: A Layer Structure with Large-pore Asymmetrical Tunnels ; data_wies18 _database_code_CSD 209302 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H8 Li N O4' _chemical_formula_weight 153.06 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 P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.2961(2) _cell_length_b 7.8521(3) _cell_length_c 7.9506(4) _cell_angle_alpha 90.030(2) _cell_angle_beta 106.037(2) _cell_angle_gamma 95.972(3) _cell_volume 315.89(2) _cell_formula_units_Z 2 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 9549 _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 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.609 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 160 _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type DELABS _exptl_absorpt_correction_T_min 0.657 _exptl_absorpt_correction_T_max 0.900 _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 9549 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 27.22 _reflns_number_total 1312 _reflns_number_gt 1269 _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. The absolute structure could not be reliably determined with this experiment. Friedel opposites were merged because of the absence of heavy atoms. ; _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^)+(0.0201P)^2^+0.0823P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.7(10) _refine_ls_number_reflns 1312 _refine_ls_number_parameters 263 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0278 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0627 _refine_ls_wR_factor_gt 0.0614 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.065 _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 N1 N 0.5623(4) 1.7987(3) -0.3282(3) 0.0166(4) Uani 1 1 d . . . Li1 Li 0.0643(8) 1.5023(5) -0.2458(5) 0.0210(8) Uani 1 1 d . . . N2 N -0.1250(5) 1.3234(3) 0.3083(3) 0.0176(4) Uani 1 1 d . . . Li2 Li 0.2663(9) 2.0219(5) 0.1945(5) 0.0210(8) Uani 1 1 d . . . O11 O 0.1939(4) 1.9349(2) -0.0384(2) 0.0238(4) Uani 1 1 d . . . C11 C 0.2473(5) 1.8582(3) -0.1596(3) 0.0163(4) Uani 1 1 d . . . O12 O 0.0887(3) 1.7523(2) -0.2684(2) 0.0197(4) Uani 1 1 d . . . C12 C 0.5282(5) 1.8975(3) -0.1772(3) 0.0170(5) Uani 1 1 d . . . O13 O 0.7162(3) 2.4086(2) -0.3455(2) 0.0258(4) Uani 1 1 d . . . C13 C 0.5998(5) 2.0893(3) -0.1920(3) 0.0193(5) Uani 1 1 d . . . O14 O 0.2984(3) 2.4590(2) -0.3891(2) 0.0187(4) Uani 1 1 d . . . C14 C 0.4006(5) 2.1715(3) -0.3355(3) 0.0204(5) Uani 1 1 d . . . C15 C 0.4806(4) 2.3599(3) -0.3571(3) 0.0168(4) Uani 1 1 d . . . C21 C 0.1755(4) 1.3761(3) 0.1189(3) 0.0160(4) Uani 1 1 d . . . O21 O 0.3112(3) 1.2747(2) 0.2195(2) 0.0198(4) Uani 1 1 d . . . C22 C -0.0662(5) 1.4325(3) 0.1659(3) 0.0165(4) Uani 1 1 d . . . O22 O 0.2260(4) 1.4398(2) -0.0134(2) 0.0232(4) Uani 1 1 d . . . O23 O -0.4237(3) 1.9370(2) 0.3447(2) 0.0196(4) Uani 1 1 d . . . C23 C -0.0200(5) 1.6226(3) 0.2211(3) 0.0171(4) Uani 1 1 d . . . O24 O -0.0475(3) 1.9750(2) 0.2708(2) 0.0213(4) Uani 1 1 d . . . C24 C -0.2530(5) 1.6871(3) 0.2721(3) 0.0186(5) Uani 1 1 d . . . C25 C -0.2366(5) 1.8797(3) 0.2988(3) 0.0164(4) Uani 1 1 d . . . H23A H 0.153(6) 1.643(4) 0.325(4) 0.023(7) Uiso 1 1 d . . . H24A H -0.287(5) 1.633(3) 0.383(3) 0.011(6) Uiso 1 1 d . . . H13B H 0.600(6) 2.151(4) -0.077(4) 0.024(7) Uiso 1 1 d . . . H14B H 0.373(7) 2.115(4) -0.456(5) 0.038(9) Uiso 1 1 d . . . H14A H 0.217(7) 2.165(4) -0.307(4) 0.028(8) Uiso 1 1 d . . . H24B H -0.411(6) 1.660(4) 0.176(4) 0.018(7) Uiso 1 1 d . . . H13A H 0.775(6) 2.114(4) -0.208(4) 0.019(7) Uiso 1 1 d . . . H12A H 0.644(6) 1.857(3) -0.074(4) 0.013(6) Uiso 1 1 d . . . H23B H 0.018(6) 1.687(4) 0.126(4) 0.022(7) Uiso 1 1 d . . . H22A H -0.216(6) 1.408(3) 0.067(4) 0.015(7) Uiso 1 1 d . . . H2A H -0.286(8) 1.327(4) 0.309(5) 0.033(9) Uiso 1 1 d . . . H1B H 0.733(7) 1.779(3) -0.316(4) 0.013(7) Uiso 1 1 d . . . H1A H 0.473(6) 1.702(4) -0.343(3) 0.013(6) Uiso 1 1 d . . . H2B H -0.097(6) 1.214(4) 0.291(4) 0.027(8) Uiso 1 1 d . . . H1C H 0.520(5) 1.853(4) -0.431(4) 0.014(6) Uiso 1 1 d . . . H2C H -0.018(8) 1.364(5) 0.414(6) 0.049(11) 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 N1 0.0167(11) 0.0141(9) 0.0208(10) 0.0008(8) 0.0082(8) 0.0021(8) Li1 0.019(2) 0.0201(19) 0.024(2) 0.0000(16) 0.0064(16) 0.0033(16) N2 0.0186(11) 0.0152(10) 0.0205(11) -0.0004(8) 0.0076(8) 0.0021(8) Li2 0.023(2) 0.0205(19) 0.0211(19) 0.0000(15) 0.0074(16) 0.0039(16) O11 0.0304(11) 0.0250(9) 0.0198(8) -0.0019(7) 0.0127(7) 0.0046(7) C11 0.0189(12) 0.0154(10) 0.0159(11) 0.0038(8) 0.0062(8) 0.0041(9) O12 0.0162(9) 0.0177(8) 0.0248(9) -0.0034(6) 0.0058(7) 0.0006(6) C12 0.0188(12) 0.0176(11) 0.0148(11) 0.0006(8) 0.0051(9) 0.0014(9) O13 0.0183(9) 0.0238(9) 0.0347(10) 0.0033(7) 0.0071(7) 0.0003(7) C13 0.0195(13) 0.0160(11) 0.0213(11) -0.0004(9) 0.0049(9) -0.0007(9) O14 0.0211(9) 0.0160(7) 0.0204(8) 0.0004(6) 0.0070(7) 0.0042(6) C14 0.0160(13) 0.0157(11) 0.0277(12) 0.0017(9) 0.0032(9) 0.0006(9) C15 0.0184(12) 0.0167(10) 0.0154(10) -0.0007(8) 0.0051(8) 0.0007(9) C21 0.0171(12) 0.0130(10) 0.0171(10) -0.0017(8) 0.0039(8) -0.0001(8) O21 0.0199(9) 0.0173(7) 0.0231(8) 0.0034(6) 0.0069(7) 0.0039(6) C22 0.0170(12) 0.0161(10) 0.0173(11) 0.0016(8) 0.0058(9) 0.0027(8) O22 0.0242(10) 0.0272(9) 0.0203(9) 0.0035(7) 0.0092(7) 0.0035(7) O23 0.0203(9) 0.0191(8) 0.0226(9) 0.0021(7) 0.0101(7) 0.0053(7) C23 0.0193(12) 0.0139(10) 0.0197(11) 0.0007(8) 0.0082(9) 0.0017(8) O24 0.0224(10) 0.0173(8) 0.0280(9) -0.0009(7) 0.0135(7) 0.0007(7) C24 0.0188(12) 0.0162(10) 0.0228(12) 0.0005(8) 0.0088(9) 0.0024(8) C25 0.0200(12) 0.0160(10) 0.0137(10) 0.0018(8) 0.0049(8) 0.0040(9) _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 N1 C12 1.491(3) . ? N1 H1B 0.91(3) . ? N1 H1A 0.84(3) . ? N1 H1C 0.91(3) . ? Li1 O13 1.865(4) 1_445 ? Li1 O22 1.898(5) . ? Li1 O14 1.954(5) 1_545 ? Li1 O12 1.965(4) . ? N2 C22 1.501(3) . ? N2 H2A 0.86(4) . ? N2 H2B 0.90(3) . ? N2 H2C 0.91(4) . ? Li2 O11 1.896(4) . ? Li2 O24 1.922(4) . ? Li2 O23 1.926(5) 1_655 ? Li2 O21 1.978(4) 1_565 ? O11 C11 1.248(3) . ? C11 O12 1.264(3) . ? C11 C12 1.532(3) . ? C12 C13 1.526(3) . ? C12 H12A 0.96(3) . ? O13 C15 1.244(3) . ? O13 Li1 1.865(5) 1_665 ? C13 C14 1.520(3) . ? C13 H13B 1.03(3) . ? C13 H13A 0.97(3) . ? O14 C15 1.274(3) . ? O14 Li1 1.954(5) 1_565 ? C14 C15 1.519(3) . ? C14 H14B 1.02(4) . ? C14 H14A 1.05(3) . ? C21 O22 1.248(3) . ? C21 O21 1.262(3) . ? C21 C22 1.535(3) . ? O21 Li2 1.978(4) 1_545 ? C22 C23 1.532(3) . ? C22 H22A 0.95(3) . ? O23 C25 1.269(3) . ? O23 Li2 1.926(5) 1_455 ? C23 C24 1.533(3) . ? C23 H23A 1.05(3) . ? C23 H23B 0.97(3) . ? O24 C25 1.257(3) . ? C24 C25 1.518(3) . ? C24 H24A 1.03(3) . ? C24 H24B 0.97(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 C12 N1 H1B 113.2(18) . . ? C12 N1 H1A 111.8(18) . . ? H1B N1 H1A 106(3) . . ? C12 N1 H1C 114.2(17) . . ? H1B N1 H1C 103(2) . . ? H1A N1 H1C 108(2) . . ? O13 Li1 O22 116.5(2) 1_445 . ? O13 Li1 O14 112.8(2) 1_445 1_545 ? O22 Li1 O14 108.0(2) . 1_545 ? O13 Li1 O12 109.4(2) 1_445 . ? O22 Li1 O12 111.7(2) . . ? O14 Li1 O12 96.69(19) 1_545 . ? C22 N2 H2A 110(2) . . ? C22 N2 H2B 110(2) . . ? H2A N2 H2B 110(3) . . ? C22 N2 H2C 110(2) . . ? H2A N2 H2C 108(3) . . ? H2B N2 H2C 109(3) . . ? O11 Li2 O24 108.4(2) . . ? O11 Li2 O23 111.3(2) . 1_655 ? O24 Li2 O23 114.5(2) . 1_655 ? O11 Li2 O21 114.8(2) . 1_565 ? O24 Li2 O21 99.1(2) . 1_565 ? O23 Li2 O21 108.2(2) 1_655 1_565 ? C11 O11 Li2 153.9(2) . . ? O11 C11 O12 125.3(2) . . ? O11 C11 C12 116.8(2) . . ? O12 C11 C12 117.9(2) . . ? C11 O12 Li1 124.7(2) . . ? N1 C12 C13 111.23(19) . . ? N1 C12 C11 110.80(18) . . ? C13 C12 C11 111.69(19) . . ? N1 C12 H12A 106.8(16) . . ? C13 C12 H12A 109.9(15) . . ? C11 C12 H12A 106.2(16) . . ? C15 O13 Li1 158.9(2) . 1_665 ? C14 C13 C12 113.70(19) . . ? C14 C13 H13B 105.2(18) . . ? C12 C13 H13B 108.5(17) . . ? C14 C13 H13A 109.7(17) . . ? C12 C13 H13A 111.8(17) . . ? H13B C13 H13A 108(2) . . ? C15 O14 Li1 127.72(19) . 1_565 ? C15 C14 C13 113.55(19) . . ? C15 C14 H14B 105.1(19) . . ? C13 C14 H14B 112.7(19) . . ? C15 C14 H14A 106.4(17) . . ? C13 C14 H14A 110.0(17) . . ? H14B C14 H14A 109(3) . . ? O13 C15 O14 123.8(2) . . ? O13 C15 C14 119.0(2) . . ? O14 C15 C14 117.2(2) . . ? O22 C21 O21 125.5(2) . . ? O22 C21 C22 116.6(2) . . ? O21 C21 C22 117.84(19) . . ? C21 O21 Li2 126.12(19) . 1_545 ? N2 C22 C23 111.09(19) . . ? N2 C22 C21 109.65(19) . . ? C23 C22 C21 110.65(18) . . ? N2 C22 H22A 105.3(16) . . ? C23 C22 H22A 112.1(16) . . ? C21 C22 H22A 107.9(17) . . ? C21 O22 Li1 142.5(2) . . ? C25 O23 Li2 127.13(19) . 1_455 ? C22 C23 C24 113.40(19) . . ? C22 C23 H23A 108.7(16) . . ? C24 C23 H23A 110.4(17) . . ? C22 C23 H23B 108.0(17) . . ? C24 C23 H23B 110.6(18) . . ? H23A C23 H23B 105(2) . . ? C25 O24 Li2 154.3(2) . . ? C25 C24 C23 115.35(19) . . ? C25 C24 H24A 106.7(15) . . ? C23 C24 H24A 113.9(15) . . ? C25 C24 H24B 104.1(17) . . ? C23 C24 H24B 108.2(17) . . ? H24A C24 H24B 108(2) . . ? O24 C25 O23 123.1(2) . . ? O24 C25 C24 120.0(2) . . ? O23 C25 C24 116.9(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 O24 Li2 O11 C11 -137.2(4) . . . . ? O23 Li2 O11 C11 -10.4(6) 1_655 . . . ? O21 Li2 O11 C11 113.0(4) 1_565 . . . ? Li2 O11 C11 O12 137.4(4) . . . . ? Li2 O11 C11 C12 -43.1(5) . . . . ? O11 C11 O12 Li1 -95.8(3) . . . . ? C12 C11 O12 Li1 84.6(3) . . . . ? O13 Li1 O12 C11 148.0(2) 1_445 . . . ? O22 Li1 O12 C11 17.5(3) . . . . ? O14 Li1 O12 C11 -94.9(2) 1_545 . . . ? O11 C11 C12 N1 -179.3(2) . . . . ? O12 C11 C12 N1 0.3(3) . . . . ? O11 C11 C12 C13 -54.7(3) . . . . ? O12 C11 C12 C13 124.9(2) . . . . ? N1 C12 C13 C14 71.4(3) . . . . ? C11 C12 C13 C14 -53.0(3) . . . . ? C12 C13 C14 C15 -176.6(2) . . . . ? Li1 O13 C15 O14 82.8(6) 1_665 . . . ? Li1 O13 C15 C14 -98.3(6) 1_665 . . . ? Li1 O14 C15 O13 -121.8(3) 1_565 . . . ? Li1 O14 C15 C14 59.4(3) 1_565 . . . ? C13 C14 C15 O13 39.9(3) . . . . ? C13 C14 C15 O14 -141.2(2) . . . . ? O22 C21 O21 Li2 -89.7(3) . . . 1_545 ? C22 C21 O21 Li2 92.9(3) . . . 1_545 ? O22 C21 C22 N2 170.7(2) . . . . ? O21 C21 C22 N2 -11.8(3) . . . . ? O22 C21 C22 C23 -66.5(3) . . . . ? O21 C21 C22 C23 111.1(2) . . . . ? O21 C21 O22 Li1 141.9(3) . . . . ? C22 C21 O22 Li1 -40.7(4) . . . . ? O13 Li1 O22 C21 -16.5(5) 1_445 . . . ? O14 Li1 O22 C21 -144.7(3) 1_545 . . . ? O12 Li1 O22 C21 110.2(3) . . . . ? N2 C22 C23 C24 -57.3(3) . . . . ? C21 C22 C23 C24 -179.30(19) . . . . ? O11 Li2 O24 C25 54.3(6) . . . . ? O23 Li2 O24 C25 -70.7(6) 1_655 . . . ? O21 Li2 O24 C25 174.4(4) 1_565 . . . ? C22 C23 C24 C25 -170.3(2) . . . . ? Li2 O24 C25 O23 -172.3(4) . . . . ? Li2 O24 C25 C24 5.6(6) . . . . ? Li2 O23 C25 O24 82.7(3) 1_455 . . . ? Li2 O23 C25 C24 -95.3(3) 1_455 . . . ? C23 C24 C25 O24 3.4(3) . . . . ? C23 C24 C25 O23 -178.55(19) . . . . ? 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 H2A O21 0.86(4) 2.05(4) 2.856(3) 156(3) 1_455 N1 H1B O12 0.91(3) 1.85(3) 2.759(3) 174(3) 1_655 N1 H1A O14 0.84(3) 2.02(3) 2.855(3) 172(3) 1_545 N2 H2B O24 0.90(3) 1.94(3) 2.836(3) 175(3) 1_545 N1 H1C O23 0.91(3) 1.99(3) 2.836(3) 155(2) 1_654 N2 H2C O14 0.91(4) 2.03(4) 2.910(3) 163(4) 1_546 _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 27.22 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 0.165 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.038