# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_LiNaIOR2
_database_code_depnum_ccdc_archive 'CCDC 1880097'
_audit_update_record             
;
2019-01-18 deposited with the CCDC.
2019-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H5 Li0.40 N2 Na0.60 O5'
_chemical_formula_weight         189.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0008 0.0003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.1353 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   3.543(5)
_cell_length_b                   18.058(8)
_cell_length_c                   10.517(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.35(10)
_cell_angle_gamma                90
_cell_volume                     672.3(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    643
_cell_measurement_theta_min      4
_cell_measurement_theta_max      40

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_F_000             387
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.774
_shelx_estimated_absorpt_T_min   0.718
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3110
_exptl_absorpt_correction_T_max  0.7520
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2684
_diffrn_reflns_av_unetI/netI     0.1436
_diffrn_reflns_av_R_equivalents  0.1200
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.869
_diffrn_reflns_theta_max         61.437
_diffrn_reflns_theta_full        61.437
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             981
_reflns_number_gt                415
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1269P)²+4.0069P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.008(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         981
_refine_ls_number_parameters     138
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.2301
_refine_ls_R_factor_gt           0.1123
_refine_ls_wR_factor_ref         0.3452
_refine_ls_wR_factor_gt          0.2684
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.035
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.052(3) 0.7111(6) 0.5573(9) 0.067(3) Uani 1 1 d . . . . .
H1 H -0.0395 0.7530 0.5320 0.080 Uiso 1 1 calc R U . . .
Li1 Li 0.694(2) 0.4688(4) 0.8668(7) 0.081(4) Uani 0.40(2) 1 d . . P A 1
C2 C 0.162(3) 0.6598(9) 0.4661(15) 0.074(4) Uani 1 1 d . . . . .
N3 N 0.297(3) 0.5949(6) 0.5173(9) 0.071(3) Uani 1 1 d . . . . .
H3 H 0.3639 0.5620 0.4636 0.085 Uiso 1 1 calc R U . . .
C4 C 0.340(4) 0.5752(10) 0.6446(12) 0.073(4) Uani 1 1 d . . . . .
C5 C 0.215(3) 0.6321(8) 0.7320(12) 0.068(4) Uani 1 1 d . . . . .
C6 C 0.083(3) 0.6971(7) 0.6847(11) 0.064(4) Uani 1 1 d . . . . .
H6 H 0.0115 0.7336 0.7412 0.077 Uiso 1 1 calc R U . . .
O7 O 0.134(3) 0.6743(5) 0.3543(8) 0.085(3) Uani 1 1 d . . . . .
O8 O 0.485(3) 0.5150(6) 0.6708(8) 0.076(3) Uani 1 1 d . . . . .
C9 C 0.243(4) 0.6208(9) 0.8736(13) 0.079(4) Uani 1 1 d . . . . .
O10 O 0.296(3) 0.5580(6) 0.9161(9) 0.107(4) Uani 1 1 d . . . . .
O11 O 0.127(3) 0.6756(5) 0.9405(8) 0.085(3) Uani 1 1 d . . . . .
O12 O 0.035(14) 0.412(3) 0.844(3) 0.061(13) Uani 0.35(6) 1 d D U P A 2
O12B O 0.220(8) 0.3818(13) 0.8565(13) 0.065(8) Uani 0.65(6) 1 d D . P A 1
Na1 Na 0.694(2) 0.4688(4) 0.8668(7) 0.081(4) Uani 0.60(2) 1 d . . P A 2
H2 H 0.01(2) 0.363(4) 0.800(11) 0.12(6) Uiso 1 1 d D . . . .
H5 H 0.10(3) 0.400(8) 0.935(3) 1.4(13) Uiso 1 1 d D . . . .


_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 C6 1.364(14) . ?
N1 C2 1.401(16) . ?
N1 H1 0.8600 . ?
Li1 O10 2.217(13) . ?
Li1 O12B 2.299(18) . ?
Li1 O8 2.317(11) . ?
Li1 O10 2.333(12) 3_667 ?
Li1 O12B 2.44(4) 1_655 ?
Li1 Li1 3.366(15) 3_667 ?
C2 O7 1.205(15) . ?
C2 N3 1.368(16) . ?
N3 C4 1.387(15) . ?
N3 H3 0.8600 . ?
C4 O8 1.231(15) . ?
C4 C5 1.458(19) . ?
C5 C6 1.351(16) . ?
C5 C9 1.502(18) . ?
C6 H6 0.9300 . ?
O8 Na1 2.317(11) . ?
C9 O10 1.231(15) . ?
C9 O11 1.291(16) . ?
O10 Na1 2.217(13) . ?
O10 Na1 2.333(12) 3_667 ?
O10 Li1 2.333(12) 3_667 ?
O10 Na1 2.704(15) 1_455 ?
O12 Na1 1.61(6) 1_455 ?
O12 Na1 2.56(4) . ?
O12 H2 1.00(2) . ?
O12 H5 1.00(2) . ?
O12B Li1 2.44(4) 1_455 ?
O12B H2 1.00(2) . ?
O12B H5 1.00(2) . ?
Na1 O12 1.61(6) 1_655 ?
Na1 O10 2.333(12) 3_667 ?
Na1 O10 2.704(15) 1_655 ?
Na1 Na1 3.366(15) 3_667 ?
Na1 Na1 3.543(5) 1_455 ?
Na1 Na1 3.649(15) 3_767 ?
Na1 H5 2.56(16) . ?

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
C6 N1 C2 122.4(12) . . ?
C6 N1 H1 118.8 . . ?
C2 N1 H1 118.8 . . ?
O10 Li1 O12B 92.1(10) . . ?
O10 Li1 O8 76.3(4) . . ?
O12B Li1 O8 89.9(6) . . ?
O10 Li1 O10 84.6(5) . 3_667 ?
O12B Li1 O10 83.5(5) . 3_667 ?
O8 Li1 O10 159.6(5) . 3_667 ?
O10 Li1 O12B 166.3(6) . 1_655 ?
O12B Li1 O12B 96.6(9) . 1_655 ?
O8 Li1 O12B 114.1(5) . 1_655 ?
O10 Li1 O12B 85.9(5) 3_667 1_655 ?
O10 Li1 Li1 43.6(3) . 3_667 ?
O12B Li1 Li1 86.8(6) . 3_667 ?
O8 Li1 Li1 119.6(4) . 3_667 ?
O10 Li1 Li1 41.0(3) 3_667 3_667 ?
O12B Li1 Li1 126.2(5) 1_655 3_667 ?
O7 C2 N3 125.7(13) . . ?
O7 C2 N1 120.6(14) . . ?
N3 C2 N1 113.6(13) . . ?
C2 N3 C4 128.4(12) . . ?
C2 N3 H3 115.8 . . ?
C4 N3 H3 115.8 . . ?
O8 C4 N3 118.0(13) . . ?
O8 C4 C5 128.0(13) . . ?
N3 C4 C5 113.9(14) . . ?
C6 C5 C4 119.3(13) . . ?
C6 C5 C9 119.3(13) . . ?
C4 C5 C9 121.4(14) . . ?
C5 C6 N1 122.4(12) . . ?
C5 C6 H6 118.8 . . ?
N1 C6 H6 118.8 . . ?
C4 O8 Na1 129.3(8) . . ?
C4 O8 Li1 129.3(8) . . ?
O10 C9 O11 123.7(13) . . ?
O10 C9 C5 119.2(14) . . ?
O11 C9 C5 115.3(14) . . ?
C9 O10 Na1 132.3(10) . . ?
C9 O10 Li1 132.3(10) . . ?
C9 O10 Na1 122.9(9) . 3_667 ?
Na1 O10 Na1 95.4(5) . 3_667 ?
C9 O10 Li1 122.9(9) . 3_667 ?
Li1 O10 Li1 95.4(5) . 3_667 ?
C9 O10 Na1 111.9(10) . 1_455 ?
Na1 O10 Na1 91.6(5) . 1_455 ?
Na1 O10 Na1 92.5(4) 3_667 1_455 ?
Na1 O12 Na1 114.6(18) 1_455 . ?
Na1 O12 H2 125(5) 1_455 . ?
Na1 O12 H2 118(6) . . ?
Na1 O12 H5 98(4) 1_455 . ?
Na1 O12 H5 79(9) . . ?
H2 O12 H5 106(3) . . ?
Li1 O12B Li1 96.6(9) . 1_455 ?
Li1 O12B H2 143(8) . . ?
Li1 O12B H2 72(3) 1_455 . ?
Li1 O12B H5 93(10) . . ?
Li1 O12B H5 54(3) 1_455 . ?
H2 O12B H5 106(3) . . ?
O12 Na1 O10 170.6(12) 1_655 . ?
O12 Na1 O8 108.2(13) 1_655 . ?
O10 Na1 O8 76.3(4) . . ?
O12 Na1 O10 91.7(13) 1_655 3_667 ?
O10 Na1 O10 84.6(5) . 3_667 ?
O8 Na1 O10 159.6(5) . 3_667 ?
O12 Na1 O12 114.6(18) 1_655 . ?
O10 Na1 O12 74.1(13) . . ?
O8 Na1 O12 78.7(11) . . ?
O10 Na1 O12 89.1(9) 3_667 . ?
O12 Na1 O10 79.6(10) 1_655 1_655 ?
O10 Na1 O10 91.6(5) . 1_655 ?
O8 Na1 O10 100.2(4) . 1_655 ?
O10 Na1 O10 87.5(5) 3_667 1_655 ?
O12 Na1 O10 165.5(12) . 1_655 ?
O12 Na1 Na1 132.1(13) 1_655 3_667 ?
O10 Na1 Na1 43.6(3) . 3_667 ?
O8 Na1 Na1 119.6(4) . 3_667 ?
O10 Na1 Na1 41.0(3) 3_667 3_667 ?
O12 Na1 Na1 78.9(7) . 3_667 ?
O10 Na1 Na1 89.3(4) 1_655 3_667 ?
O12 Na1 Na1 139.0(10) 1_655 1_455 ?
O10 Na1 Na1 49.7(4) . 1_455 ?
O8 Na1 Na1 73.6(3) . 1_455 ?
O10 Na1 Na1 88.6(4) 3_667 1_455 ?
O12 Na1 Na1 24.4(13) . 1_455 ?
O10 Na1 Na1 141.3(3) 1_655 1_455 ?
Na1 Na1 Na1 63.7(3) 3_667 1_455 ?
O12 Na1 Na1 83.4(12) 1_655 3_767 ?
O10 Na1 Na1 87.7(4) . 3_767 ?
O8 Na1 Na1 136.9(5) . 3_767 ?
O10 Na1 Na1 47.8(3) 3_667 3_767 ?
O12 Na1 Na1 135.0(7) . 3_767 ?
O10 Na1 Na1 39.7(3) 1_655 3_767 ?
Na1 Na1 Na1 60.5(3) 3_667 3_767 ?
Na1 Na1 Na1 124.2(3) 1_455 3_767 ?
O12 Na1 H5 111(3) 1_655 . ?
O10 Na1 H5 76(2) . . ?
O8 Na1 H5 100.9(14) . . ?
O10 Na1 H5 66.6(12) 3_667 . ?
O12 Na1 H5 22.6(8) . . ?
O10 Na1 H5 151.7(14) 1_655 . ?
Na1 Na1 H5 63.9(17) 3_667 . ?
Na1 Na1 H5 34(2) 1_455 . ?
Na1 Na1 H5 113.5(12) 3_767 . ?

_refine_diff_density_max         0.351
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.087

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_NaIOR
_database_code_depnum_ccdc_archive 'CCDC 1884568'
_audit_update_record             
;
2019-01-18 deposited with the CCDC.
2019-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H5 N2 Na O5'
_chemical_formula_weight         196.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Na Na 0.1353 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   3.5627(2)
_cell_length_b                   18.0624(7)
_cell_length_c                   10.6069(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.132(3)
_cell_angle_gamma                90
_cell_volume                     682.09(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    532
_cell_measurement_theta_min      2
_cell_measurement_theta_max      30

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.910
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    2.028
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6023
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9539
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_av_R_equivalents  0.1147
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.837
_diffrn_reflns_theta_max         72.490
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1343
_reflns_number_gt                896
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0735P)²+1.1147P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0063(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1343
_refine_ls_number_parameters     127
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1682
_refine_ls_wR_factor_gt          0.1387
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.017
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0417(10) 0.71034(18) 0.5498(3) 0.0335(8) Uani 1 1 d . . . . .
H1 H -0.0467 0.7522 0.5237 0.040 Uiso 1 1 calc R U . . .
Na1 Na 0.7069(5) 0.46915(9) 0.86840(15) 0.0374(5) Uani 1 1 d . . . . .
C2 C 0.1577(12) 0.6603(2) 0.4629(3) 0.0318(9) Uani 1 1 d . . . . .
N3 N 0.2954(10) 0.59534(19) 0.5125(3) 0.0331(8) Uani 1 1 d . . . . .
H3 H 0.3693 0.5629 0.4596 0.040 Uiso 1 1 calc R U . . .
C4 C 0.3284(11) 0.5764(2) 0.6391(4) 0.0289(9) Uani 1 1 d . . . . .
C5 C 0.1986(11) 0.6319(2) 0.7254(3) 0.0282(8) Uani 1 1 d . . . . .
C6 C 0.0609(11) 0.6964(2) 0.6762(4) 0.0303(9) Uani 1 1 d . . . . .
H6 H -0.0235 0.7324 0.7310 0.036 Uiso 1 1 calc R U . . .
O7 O 0.1441(10) 0.67224(17) 0.3492(3) 0.0440(8) Uani 1 1 d . . . . .
O8 O 0.4750(9) 0.51578(15) 0.6662(3) 0.0391(8) Uani 1 1 d . . . . .
C9 C 0.1845(11) 0.6205(2) 0.8652(4) 0.0286(9) Uani 1 1 d . . . . .
O10 O 0.2338(9) 0.55607(15) 0.9085(3) 0.0364(7) Uani 1 1 d . . . . .
O11 O 0.1093(8) 0.67632(15) 0.9311(3) 0.0360(7) Uani 1 1 d . . . . .
O12 O 0.2309(9) 0.38069(17) 0.8607(3) 0.0422(8) Uani 1 1 d D . . . .
H12A H 0.135(19) 0.357(3) 0.789(4) 0.09(2) Uiso 1 1 d D . . . .
H12B H 0.123(17) 0.360(3) 0.930(4) 0.08(2) Uiso 1 1 d D . . . .


_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 C6 1.364(5) . ?
N1 C2 1.366(5) . ?
N1 H1 0.8600 . ?
Na1 O12 2.329(4) . ?
Na1 O10 2.354(3) . ?
Na1 O10 2.412(3) 3_667 ?
Na1 O8 2.421(3) . ?
Na1 O12 2.461(4) 1_655 ?
Na1 O10 2.472(3) 1_655 ?
Na1 Na1 3.394(3) 3_667 ?
Na1 Na1 3.5627(2) 1_455 ?
Na1 Na1 3.601(3) 3_767 ?
C2 O7 1.225(5) . ?
C2 N3 1.369(5) . ?
N3 C4 1.386(5) . ?
N3 H3 0.8600 . ?
C4 O8 1.242(5) . ?
C4 C5 1.446(5) . ?
C5 C6 1.360(5) . ?
C5 C9 1.500(5) . ?
C6 H6 0.9300 . ?
C9 O11 1.261(5) . ?
C9 O10 1.262(5) . ?
O10 Na1 2.412(3) 3_667 ?
O10 Na1 2.472(3) 1_455 ?
O12 Na1 2.461(4) 1_455 ?
O12 H12A 0.93(2) . ?
O12 H12B 0.93(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
C6 N1 C2 122.4(3) . . ?
C6 N1 H1 118.8 . . ?
C2 N1 H1 118.8 . . ?
O12 Na1 O10 86.48(12) . . ?
O12 Na1 O10 86.67(12) . 3_667 ?
O10 Na1 O10 89.19(11) . 3_667 ?
O12 Na1 O8 89.06(12) . . ?
O10 Na1 O8 72.84(11) . . ?
O10 Na1 O8 161.75(13) 3_667 . ?
O12 Na1 O12 96.07(12) . 1_655 ?
O10 Na1 O12 171.23(13) . 1_655 ?
O10 Na1 O12 82.60(11) 3_667 1_655 ?
O8 Na1 O12 115.51(12) . 1_655 ?
O12 Na1 O10 171.50(13) . 1_655 ?
O10 Na1 O10 95.14(11) . 1_655 ?
O10 Na1 O10 85.01(11) 3_667 1_655 ?
O8 Na1 O10 99.40(11) . 1_655 ?
O12 Na1 O10 81.13(11) 1_655 1_655 ?
O12 Na1 Na1 85.19(10) . 3_667 ?
O10 Na1 Na1 45.28(8) . 3_667 ?
O10 Na1 Na1 43.91(8) 3_667 3_667 ?
O8 Na1 Na1 118.05(11) . 3_667 ?
O12 Na1 Na1 126.43(11) 1_655 3_667 ?
O10 Na1 Na1 90.02(9) 1_655 3_667 ?
O12 Na1 Na1 43.38(9) . 1_455 ?
O10 Na1 Na1 43.71(8) . 1_455 ?
O10 Na1 Na1 92.93(8) 3_667 1_455 ?
O8 Na1 Na1 72.04(9) . 1_455 ?
O12 Na1 Na1 139.45(8) 1_655 1_455 ?
O10 Na1 Na1 138.86(8) 1_655 1_455 ?
Na1 Na1 Na1 62.29(6) 3_667 1_455 ?
O12 Na1 Na1 129.80(11) . 3_767 ?
O10 Na1 Na1 92.98(10) . 3_767 ?
O10 Na1 Na1 43.15(8) 3_667 3_767 ?
O8 Na1 Na1 138.44(11) . 3_767 ?
O12 Na1 Na1 78.92(9) 1_655 3_767 ?
O10 Na1 Na1 41.85(7) 1_655 3_767 ?
Na1 Na1 Na1 61.16(6) 3_667 3_767 ?
Na1 Na1 Na1 123.45(5) 1_455 3_767 ?
O7 C2 N1 123.0(4) . . ?
O7 C2 N3 122.0(4) . . ?
N1 C2 N3 114.9(3) . . ?
C2 N3 C4 126.9(3) . . ?
C2 N3 H3 116.6 . . ?
C4 N3 H3 116.6 . . ?
O8 C4 N3 117.4(3) . . ?
O8 C4 C5 127.4(4) . . ?
N3 C4 C5 115.1(3) . . ?
C6 C5 C4 118.1(4) . . ?
C6 C5 C9 118.2(3) . . ?
C4 C5 C9 123.7(3) . . ?
C5 C6 N1 122.7(4) . . ?
C5 C6 H6 118.7 . . ?
N1 C6 H6 118.7 . . ?
C4 O8 Na1 129.6(3) . . ?
O11 C9 O10 124.5(4) . . ?
O11 C9 C5 117.0(3) . . ?
O10 C9 C5 118.5(3) . . ?
C9 O10 Na1 129.9(3) . . ?
C9 O10 Na1 122.5(2) . 3_667 ?
Na1 O10 Na1 90.81(11) . 3_667 ?
C9 O10 Na1 115.4(3) . 1_455 ?
Na1 O10 Na1 95.14(11) . 1_455 ?
Na1 O10 Na1 94.99(11) 3_667 1_455 ?
Na1 O12 Na1 96.07(12) . 1_455 ?
Na1 O12 H12A 126(4) . . ?
Na1 O12 H12A 94(4) 1_455 . ?
Na1 O12 H12B 125(4) . . ?
Na1 O12 H12B 84(4) 1_455 . ?
H12A O12 H12B 108(6) . . ?

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.084

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_LIIOR
_database_code_depnum_ccdc_archive 'CCDC 1884569'
_audit_update_record             
;
2019-01-18 deposited with the CCDC.
2019-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H5 Li N2 O5'
_chemical_formula_weight         180.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0008 0.0003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   3.5184(2)
_cell_length_b                   18.1563(11)
_cell_length_c                   10.3331(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.778(4)
_cell_angle_gamma                90
_cell_volume                     660.03(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    210
_cell_measurement_theta_min      4
_cell_measurement_theta_max      20

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.409
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6839
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7038
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.871
_diffrn_reflns_theta_max         65.107
_diffrn_reflns_theta_full        65.107
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1123
_reflns_number_gt                813
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0552P)²+0.4339P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1123
_refine_ls_number_parameters     126
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1236
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.071
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0813(7) 0.71162(13) 0.5712(2) 0.0267(6) Uani 1 1 d . . . . .
H1 H -0.0094 0.7537 0.5482 0.032 Uiso 1 1 calc R U . . .
Li1 Li 0.5340(16) 0.4683(3) 0.8685(5) 0.0348(12) Uani 1 1 d . . . . .
C2 C 0.1743(8) 0.66174(15) 0.4777(3) 0.0261(7) Uani 1 1 d . . . . .
N3 N 0.3137(7) 0.59613(13) 0.5238(2) 0.0270(6) Uani 1 1 d . . . . .
H3 H 0.3722 0.5637 0.4668 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3711(8) 0.57633(15) 0.6529(3) 0.0220(6) Uani 1 1 d . . . . .
C5 C 0.2681(8) 0.63250(14) 0.7451(3) 0.0205(6) Uani 1 1 d . . . . .
C6 C 0.1275(8) 0.69693(15) 0.6986(3) 0.0239(7) Uani 1 1 d . . . . .
H6 H 0.0590 0.7330 0.7577 0.029 Uiso 1 1 calc R U . . .
O7 O 0.1319(7) 0.67454(12) 0.3625(2) 0.0378(6) Uani 1 1 d . . . . .
O8 O 0.5031(6) 0.51445(10) 0.67520(19) 0.0304(5) Uani 1 1 d . . . . .
C9 C 0.3039(8) 0.62276(15) 0.8892(3) 0.0232(6) Uani 1 1 d . . . . .
O10 O 0.4411(6) 0.56398(11) 0.93235(19) 0.0316(6) Uani 1 1 d . . . . .
O11 O 0.1839(6) 0.67448(10) 0.95844(18) 0.0281(5) Uani 1 1 d . . . . .
O12 O 0.0434(6) 0.41302(12) 0.8402(2) 0.0334(6) Uani 1 1 d D . . . .
H12A H -0.029(12) 0.3833(19) 0.908(3) 0.071(14) Uiso 1 1 d D . . . .
H12B H 0.004(12) 0.3864(19) 0.764(3) 0.073(14) Uiso 1 1 d D . . . .


_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 C6 1.351(4) . ?
N1 C2 1.367(4) . ?
N1 H1 0.8600 . ?
Li1 O10 1.889(6) . ?
Li1 O12 2.014(6) . ?
Li1 O12 2.078(6) 1_655 ?
Li1 O10 2.140(6) 3_667 ?
Li1 O8 2.168(6) . ?
Li1 Li1 2.965(11) 3_667 ?
Li1 Li1 3.5184(2) 1_455 ?
C2 O7 1.219(3) . ?
C2 N3 1.371(4) . ?
N3 C4 1.394(3) . ?
N3 H3 0.8600 . ?
C4 O8 1.236(3) . ?
C4 C5 1.445(4) . ?
C5 C6 1.355(4) . ?
C5 C9 1.503(4) . ?
C6 H6 0.9300 . ?
C9 O10 1.251(3) . ?
C9 O11 1.257(3) . ?
O10 Li1 2.140(6) 3_667 ?
O12 Li1 2.078(6) 1_455 ?
O12 H12A 0.920(19) . ?
O12 H12B 0.929(19) . ?

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
C6 N1 C2 122.1(2) . . ?
C6 N1 H1 119.0 . . ?
C2 N1 H1 119.0 . . ?
O10 Li1 O12 110.9(3) . . ?
O10 Li1 O12 130.3(3) . 1_655 ?
O12 Li1 O12 118.6(3) . 1_655 ?
O10 Li1 O10 85.5(2) . 3_667 ?
O12 Li1 O10 91.6(2) . 3_667 ?
O12 Li1 O10 88.8(2) 1_655 3_667 ?
O10 Li1 O8 87.7(2) . . ?
O12 Li1 O8 91.5(2) . . ?
O12 Li1 O8 95.1(2) 1_655 . ?
O10 Li1 O8 173.1(3) 3_667 . ?
O10 Li1 Li1 46.02(16) . 3_667 ?
O12 Li1 Li1 104.3(3) . 3_667 ?
O12 Li1 Li1 113.4(3) 1_655 3_667 ?
O10 Li1 Li1 39.44(14) 3_667 3_667 ?
O8 Li1 Li1 133.7(3) . 3_667 ?
O10 Li1 Li1 79.76(19) . 1_455 ?
O12 Li1 Li1 31.24(16) . 1_455 ?
O12 Li1 Li1 149.81(16) 1_655 1_455 ?
O10 Li1 Li1 91.60(16) 3_667 1_455 ?
O8 Li1 Li1 87.84(16) . 1_455 ?
Li1 Li1 Li1 84.7(2) 3_667 1_455 ?
O7 C2 N1 122.4(3) . . ?
O7 C2 N3 122.9(3) . . ?
N1 C2 N3 114.7(2) . . ?
C2 N3 C4 127.1(2) . . ?
C2 N3 H3 116.5 . . ?
C4 N3 H3 116.5 . . ?
O8 C4 N3 117.5(2) . . ?
O8 C4 C5 128.0(3) . . ?
N3 C4 C5 114.5(2) . . ?
C6 C5 C4 118.0(3) . . ?
C6 C5 C9 118.5(2) . . ?
C4 C5 C9 123.5(2) . . ?
N1 C6 C5 123.7(3) . . ?
N1 C6 H6 118.2 . . ?
C5 C6 H6 118.2 . . ?
C4 O8 Li1 122.5(2) . . ?
O10 C9 O11 124.4(3) . . ?
O10 C9 C5 118.7(2) . . ?
O11 C9 C5 116.9(2) . . ?
C9 O10 Li1 136.7(3) . . ?
C9 O10 Li1 125.9(2) . 3_667 ?
Li1 O10 Li1 94.5(2) . 3_667 ?
Li1 O12 Li1 118.6(3) . 1_455 ?
Li1 O12 H12A 115(3) . . ?
Li1 O12 H12A 86(3) 1_455 . ?
Li1 O12 H12B 120(3) . . ?
Li1 O12 H12B 105(3) 1_455 . ?
H12A O12 H12B 107(3) . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.066

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_LiNaIOR1
_database_code_depnum_ccdc_archive 'CCDC 1880098'
_audit_update_record             
;
2019-01-18 deposited with the CCDC.
2019-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H5 Li0.68 N2 Na0.32 O5'
_chemical_formula_weight         185.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0008 0.0003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.1353 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   3.5356(2)
_cell_length_b                   18.1159(12)
_cell_length_c                   10.4169(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.693(4)
_cell_angle_gamma                90
_cell_volume                     666.92(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    3218
_cell_measurement_theta_min      4
_cell_measurement_theta_max      40

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_F_000             378
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.615
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5986
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7005
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.882
_diffrn_reflns_theta_max         66.558
_diffrn_reflns_theta_full        66.558
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1171
_reflns_number_gt                964
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+4.7217P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0034(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1171
_refine_ls_number_parameters     138
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0987
_refine_ls_wR_factor_ref         0.2083
_refine_ls_wR_factor_gt          0.2012
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.171
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0684(15) 0.7113(3) 0.5652(5) 0.0398(13) Uani 1 1 d . . . . .
H1 H -0.0201 0.7535 0.5415 0.048 Uiso 1 1 calc R U . . .
Li1 Li 0.663(3) 0.4690(4) 0.8662(7) 0.091(4) Uani 0.676(15) 1 d . . P A 1
C2 C 0.1641(19) 0.6615(3) 0.4732(6) 0.0391(15) Uani 1 1 d . . . . .
N3 N 0.3039(15) 0.5957(3) 0.5206(5) 0.0393(13) Uani 1 1 d . . . . .
H3 H 0.3663 0.5633 0.4647 0.047 Uiso 1 1 calc R U . . .
C4 C 0.3553(17) 0.5760(3) 0.6490(6) 0.0352(14) Uani 1 1 d . . . . .
C5 C 0.2430(16) 0.6319(3) 0.7391(6) 0.0320(13) Uani 1 1 d . . . . .
C6 C 0.1084(19) 0.6964(3) 0.6933(6) 0.0383(15) Uani 1 1 d . . . . .
H6 H 0.0392 0.7325 0.7516 0.046 Uiso 1 1 calc R U . . .
O7 O 0.1326(15) 0.6745(3) 0.3591(4) 0.0527(14) Uani 1 1 d . . . . .
O8 O 0.4877(13) 0.5141(2) 0.6723(4) 0.0405(12) Uani 1 1 d . . . . .
C9 C 0.270(2) 0.6222(4) 0.8826(6) 0.0424(16) Uani 1 1 d . . . . .
O10 O 0.395(2) 0.5623(3) 0.9267(5) 0.077(2) Uani 1 1 d . . . . .
O11 O 0.1586(14) 0.6752(2) 0.9496(4) 0.0432(12) Uani 1 1 d . . . . .
O12 O 0.028(4) 0.4133(7) 0.8444(9) 0.034(4) Uani 0.59(5) 1 d D . P A 2
O12B O 0.223(15) 0.386(2) 0.8480(19) 0.081(13) Uani 0.41(5) 1 d D . P A 1
Na1 Na 0.663(3) 0.4690(4) 0.8662(7) 0.091(4) Uani 0.324(15) 1 d . . P A 2
H2 H 0.021(15) 0.372(3) 0.907(5) 0.05(2) Uiso 1 1 d D . . . .
H5 H 0.05(2) 0.380(5) 0.770(6) 0.16(5) Uiso 1 1 d D . . . .


_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 C6 1.365(8) . ?
N1 C2 1.366(8) . ?
N1 H1 0.8600 . ?
Li1 O10 2.046(9) . ?
Li1 O12B 2.16(3) . ?
Li1 O10 2.246(9) 3_667 ?
Li1 O8 2.248(8) . ?
Li1 O12B 2.49(6) 1_655 ?
Li1 Li1 3.248(16) 3_667 ?
Li1 Li1 3.5356(3) 1_655 ?
Li1 Li1 3.5356(3) 1_455 ?
C2 O7 1.213(8) . ?
C2 N3 1.375(8) . ?
N3 C4 1.391(8) . ?
N3 H3 0.8600 . ?
C4 O8 1.236(7) . ?
C4 C5 1.446(8) . ?
C5 C6 1.343(9) . ?
C5 C9 1.506(9) . ?
C6 H6 0.9300 . ?
O8 Na1 2.248(8) . ?
C9 O10 1.253(8) . ?
C9 O11 1.258(8) . ?
C9 Na1 3.097(9) 3_667 ?
O10 Na1 2.046(9) . ?
O10 Na1 2.246(9) 3_667 ?
O10 Li1 2.246(9) 3_667 ?
O12 Na1 1.66(2) 1_455 ?
O12 Na1 2.465(16) . ?
O12 H2 1.00(2) . ?
O12 H5 0.99(2) . ?
O12B Li1 2.49(6) 1_455 ?
O12B H2 0.99(2) . ?
O12B H5 1.01(2) . ?
Na1 O12 1.66(2) 1_655 ?
Na1 O10 2.246(9) 3_667 ?
Na1 C9 3.097(9) 3_667 ?
Na1 Na1 3.248(16) 3_667 ?
Na1 Na1 3.5356(3) 1_655 ?
Na1 Na1 3.5356(3) 1_455 ?
Na1 Na1 3.787(17) 3_767 ?

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
C6 N1 C2 122.3(5) . . ?
C6 N1 H1 118.8 . . ?
C2 N1 H1 118.8 . . ?
O10 Li1 O12B 105.1(17) . . ?
O10 Li1 O10 81.8(3) . 3_667 ?
O12B Li1 O10 79.9(7) . 3_667 ?
O10 Li1 O8 81.9(3) . . ?
O12B Li1 O8 89.7(10) . . ?
O10 Li1 O8 157.6(6) 3_667 . ?
O10 Li1 O12B 153.4(7) . 1_655 ?
O12B Li1 O12B 98.6(16) . 1_655 ?
O10 Li1 O12B 90.9(6) 3_667 1_655 ?
O8 Li1 O12B 110.3(6) . 1_655 ?
O10 Li1 Li1 43.2(2) . 3_667 ?
O12B Li1 Li1 92.5(10) . 3_667 ?
O10 Li1 Li1 38.6(2) 3_667 3_667 ?
O8 Li1 Li1 123.4(4) . 3_667 ?
O12B Li1 Li1 125.1(6) 1_655 3_667 ?
O10 Li1 Li1 118.1(4) . 1_655 ?
O12B Li1 Li1 135.8(17) . 1_655 ?
O10 Li1 Li1 96.8(3) 3_667 1_655 ?
O8 Li1 Li1 104.4(3) . 1_655 ?
O12B Li1 Li1 37.2(5) 1_655 1_655 ?
Li1 Li1 Li1 112.3(4) 3_667 1_655 ?
O10 Li1 Li1 61.9(4) . 1_455 ?
O12B Li1 Li1 44.2(17) . 1_455 ?
O10 Li1 Li1 83.2(3) 3_667 1_455 ?
O8 Li1 Li1 75.6(3) . 1_455 ?
O12B Li1 Li1 142.8(5) 1_655 1_455 ?
Li1 Li1 Li1 67.7(4) 3_667 1_455 ?
Li1 Li1 Li1 180.0 1_655 1_455 ?
O7 C2 N1 122.8(6) . . ?
O7 C2 N3 122.8(6) . . ?
N1 C2 N3 114.5(5) . . ?
C2 N3 C4 127.1(5) . . ?
C2 N3 H3 116.4 . . ?
C4 N3 H3 116.4 . . ?
O8 C4 N3 117.4(5) . . ?
O8 C4 C5 128.2(6) . . ?
N3 C4 C5 114.4(5) . . ?
C6 C5 C4 118.7(6) . . ?
C6 C5 C9 117.8(5) . . ?
C4 C5 C9 123.5(5) . . ?
C5 C6 N1 123.0(6) . . ?
C5 C6 H6 118.5 . . ?
N1 C6 H6 118.5 . . ?
C4 O8 Na1 126.8(4) . . ?
C4 O8 Li1 126.8(4) . . ?
O10 C9 O11 124.8(6) . . ?
O10 C9 C5 118.5(6) . . ?
O11 C9 C5 116.7(6) . . ?
O10 C9 Na1 37.9(4) . 3_667 ?
O11 C9 Na1 87.5(4) . 3_667 ?
C5 C9 Na1 154.5(4) . 3_667 ?
C9 O10 Na1 139.7(5) . . ?
C9 O10 Li1 139.7(5) . . ?
C9 O10 Na1 122.0(5) . 3_667 ?
Na1 O10 Na1 98.2(3) . 3_667 ?
C9 O10 Li1 122.0(5) . 3_667 ?
Li1 O10 Li1 98.2(3) . 3_667 ?
Na1 O12 Na1 116.7(7) 1_455 . ?
Na1 O12 H2 110(3) 1_455 . ?
Na1 O12 H2 107(3) . . ?
Na1 O12 H5 125(3) 1_455 . ?
Na1 O12 H5 103(6) . . ?
H2 O12 H5 93(8) . . ?
Li1 O12B Li1 98.6(16) . 1_455 ?
Li1 O12B H2 132(4) . . ?
Li1 O12B H2 62(3) 1_455 . ?
Li1 O12B H5 125(8) . . ?
Li1 O12B H5 71(3) 1_455 . ?
H2 O12B H5 92(8) . . ?
O12 Na1 O10 155.9(7) 1_655 . ?
O12 Na1 O10 94.1(5) 1_655 3_667 ?
O10 Na1 O10 81.8(3) . 3_667 ?
O12 Na1 O8 107.0(5) 1_655 . ?
O10 Na1 O8 81.9(3) . . ?
O10 Na1 O8 157.6(6) 3_667 . ?
O12 Na1 O12 116.7(7) 1_655 . ?
O10 Na1 O12 86.5(6) . . ?
O10 Na1 O12 83.0(4) 3_667 . ?
O8 Na1 O12 80.8(4) . . ?
O12 Na1 C9 75.6(4) 1_655 3_667 ?
O10 Na1 C9 101.8(3) . 3_667 ?
O10 Na1 C9 20.05(19) 3_667 3_667 ?
O8 Na1 C9 164.8(5) . 3_667 ?
O12 Na1 C9 84.7(4) . 3_667 ?
O12 Na1 Na1 128.6(6) 1_655 3_667 ?
O10 Na1 Na1 43.2(2) . 3_667 ?
O10 Na1 Na1 38.6(2) 3_667 3_667 ?
O8 Na1 Na1 123.4(4) . 3_667 ?
O12 Na1 Na1 82.9(5) . 3_667 ?
C9 Na1 Na1 58.6(2) 3_667 3_667 ?
O12 Na1 Na1 38.5(4) 1_655 1_655 ?
O10 Na1 Na1 118.1(4) . 1_655 ?
O10 Na1 Na1 96.8(3) 3_667 1_655 ?
O8 Na1 Na1 104.4(3) . 1_655 ?
O12 Na1 Na1 155.2(4) . 1_655 ?
C9 Na1 Na1 87.0(2) 3_667 1_655 ?
Na1 Na1 Na1 112.3(4) 3_667 1_655 ?
O12 Na1 Na1 141.5(4) 1_655 1_455 ?
O10 Na1 Na1 61.9(4) . 1_455 ?
O10 Na1 Na1 83.2(3) 3_667 1_455 ?
O8 Na1 Na1 75.6(3) . 1_455 ?
O12 Na1 Na1 24.8(4) . 1_455 ?
C9 Na1 Na1 93.0(2) 3_667 1_455 ?
Na1 Na1 Na1 67.7(4) 3_667 1_455 ?
Na1 Na1 Na1 180.0 1_655 1_455 ?
O12 Na1 Na1 78.8(5) 1_655 3_767 ?
O10 Na1 Na1 79.3(3) . 3_767 ?
O10 Na1 Na1 56.0(3) 3_667 3_767 ?
O8 Na1 Na1 134.8(5) . 3_767 ?
O12 Na1 Na1 137.9(5) . 3_767 ?
C9 Na1 Na1 60.3(2) 3_667 3_767 ?
Na1 Na1 Na1 59.8(2) 3_667 3_767 ?
Na1 Na1 Na1 52.5(3) 1_655 3_767 ?
Na1 Na1 Na1 127.5(3) 1_455 3_767 ?

_refine_diff_density_max         0.403
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.091


# start Validation Reply Form
_vrf_REFNR01_LiNaIOR2            
;
PROBLEM: Ratio of reflections to parameters is < 8 for a
RESPONSE: This is due to the disorder of the structure
;
_vrf_THETM01_LiNaIOR2            
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: this is due to the low scattering of the crystal
;
_vrf_PLAT029_LiNaIOR2            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.956 Why?  
RESPONSE: this is due to the low scattering of the crystal
;
_vrf_PLAT031_LiNaIOR2            
;
PROBLEM: Refined Extinction Parameter Within Range ......      2.000 Sigma 
RESPONSE: ...
;
_vrf_PLAT088_LiNaIOR2            
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.11 Note  
RESPONSE: This is due to the disorder of the structure
;
_vrf_PLAT149_LiNaIOR2            
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.10 Degree
RESPONSE: This is due to the disorder of the structure
;
_vrf_PLAT340_LiNaIOR2            
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01933 Ang.  
RESPONSE: this is due to the low scattering of the crystal
;
# end Validation Reply Form
