#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/46/7204677.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7204677
loop_
_publ_author_name
'Wiesbrock, Frank'
'Schmidbaur, Hubert'
_publ_section_title
;
 Lithium l-hydrogen-?-glutamate: A layer structure with asymmetrical
 tunnels formed by nets with two different macrocycles
;
_journal_issue                   45
_journal_name_full               CrystEngComm
_journal_page_first              262
_journal_paper_doi               10.1039/b304689c
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C5 H8 Li N O4'
_chemical_formula_weight         153.06
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.030(2)
_cell_angle_beta                 106.037(2)
_cell_angle_gamma                95.972(3)
_cell_formula_units_Z            2
_cell_length_a                   5.2961(2)
_cell_length_b                   7.8521(3)
_cell_length_c                   7.9506(4)
_cell_measurement_reflns_used    9549
_cell_measurement_temperature    143(2)
_cell_volume                     315.89(2)
_computing_cell_refinement       DENZO
_computing_data_collection       XPRESS
_computing_data_reduction        SCALEPACK
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      143(2)
_diffrn_measured_fraction_theta_full 0.929
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device_type  'Nonius DIP 2020'
_diffrn_measurement_method       phi-rotation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9549
_diffrn_reflns_theta_full        27.22
_diffrn_reflns_theta_max         27.22
_diffrn_reflns_theta_min         3.67
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_correction_T_min  0.657
_exptl_absorpt_correction_type   DELABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             160
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.7(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         1312
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0262
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0201P)²+0.0823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0614
_refine_ls_wR_factor_ref         0.0627
_reflns_number_gt                1269
_reflns_number_total             1312
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b304689c.txt
_cod_data_source_block           wies18
_cod_original_sg_symbol_H-M      P1
_cod_database_code               7204677
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
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_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'
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_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_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
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) . . . . ?
