# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2303329'
loop_
_audit_author_name
_audit_author_address
'Yang Li'
;Sogang University
South Korea
;
_audit_update_record             
;
2024-03-10 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2023-10-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'H12 Mg O6, 2(C5 H5 N O), 2(N O3)'
_chemical_formula_sum            'C10 H22 Mg N4 O14'
_chemical_formula_weight         446.62
_chemical_melting_point          ?
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'
Mg Mg 0.0486 0.0363 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   24.6517(11)
_cell_length_b                   6.4107(3)
_cell_length_c                   26.2782(12)
_cell_angle_alpha                90
_cell_angle_beta                 106.673(2)
_cell_angle_gamma                90
_cell_volume                     3978.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      27.33
_cell_measurement_theta_min      3.20
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1135 before and 0.1007 after correction.
The Ratio of minimum to maximum transmission is 0.8002.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 0.00 0.0760
1.00 0.00 0.00 0.0740
1.00 0.00 1.00 0.0560
0.00 0.00 1.00 0.0660
0.00 0.00 -1.00 0.1460
-1.00 0.00 1.00 0.1080
1.00 0.00 -1.00 0.1120
1.00 1.00 1.00 0.1010
-1.00 -1.00 -1.00 0.1300
1.00 1.00 0.00 0.1010
-1.00 -1.00 0.00 0.1250
-1.00 1.00 0.00 0.0760
1.00 -1.00 0.00 0.1100
0.00 -1.00 1.00 0.1110
1.00 -1.00 1.00 0.0950
-1.00 1.00 -1.00 0.0610

_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.242
_exptl_crystal_size_min          0.152
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1047
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            57494
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.574
_diffrn_reflns_theta_min         2.683
_diffrn_ambient_temperature      293.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3176
_reflns_number_total             4602
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4602
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0843
_refine_ls_restrained_S_all      1.175
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0451P)²+13.7245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1705
_refine_ls_wR_factor_ref         0.1859
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 Mg1-H3A \\sim Mg1-H3B
 with sigma of 0.02
 Mg1-H2A \\sim Mg1-H2B
 with sigma of 0.02
 Mg1-H5A \\sim Mg1-H5B
 with sigma of 0.02
3.a Free rotating group:
 O3(H3A,H3B), O5(H5A,H5B), O2(H2A,H2B)
3.b Rotating group:
 O1(H1A)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2C), C10(H10), C1(H1C), C7(H7), C4(H4), C5(H5), C9(H9),
 C8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Mg1 Mg 0.50050(6) 0.74071(15) 0.62693(5) 0.0246(2) Uani 1 1 d D . . . .
O8 O 0.44528(11) 0.2417(4) 0.70792(10) 0.0345(6) Uani 1 1 d . . . . .
O6 O 0.48804(13) 0.4564(4) 0.58999(12) 0.0387(6) Uani 1 1 d . . . . .
O1 O 0.48163(11) 0.6270(4) 0.69364(10) 0.0353(6) Uani 1 1 d . . . . .
H1A H 0.507804 0.661329 0.721487 0.053 Uiso 1 1 d R U . . .
O3 O 0.51320(11) 1.0265(4) 0.66178(12) 0.0402(6) Uani 1 1 d G . . . .
H3A H 0.490403 1.095597 0.674219 0.060 Uiso 1 1 d DG U . . .
H3B H 0.541980 1.105127 0.666581 0.060 Uiso 1 1 d DG U . . .
O7 O 0.55378(11) 0.2451(4) 0.54031(10) 0.0375(7) Uani 1 1 d . . . . .
O4 O 0.51979(12) 0.8535(4) 0.55997(11) 0.0365(6) Uani 1 1 d . . . . .
O5 O 0.58511(10) 0.6799(4) 0.66129(11) 0.0397(6) Uani 1 1 d G . . . .
H5A H 0.600732 0.561365 0.669196 0.060 Uiso 1 1 d DG U . . .
H5B H 0.612476 0.766043 0.668772 0.060 Uiso 1 1 d DG U . . .
O2 O 0.41573(10) 0.8046(4) 0.59271(12) 0.0425(7) Uani 1 1 d G . . . .
H2A H 0.388773 0.717276 0.583051 0.064 Uiso 1 1 d DG U . . .
H2B H 0.400072 0.922636 0.584151 0.064 Uiso 1 1 d DG U . . .
O9 O 0.33331(11) 0.4963(4) 0.57131(12) 0.0500(7) Uani 1 1 d . . . . .
O10 O 0.38659(12) 0.2285(4) 0.57185(13) 0.0518(8) Uani 1 1 d . . . . .
O13 O 0.66660(12) -0.0042(4) 0.67596(14) 0.0598(9) Uani 1 1 d . . . . .
O12 O 0.61257(13) 0.2591(4) 0.67641(15) 0.0594(9) Uani 1 1 d . . . . .
O14 O 0.70126(13) 0.3049(5) 0.68596(14) 0.0616(9) Uani 1 1 d . . . . .
N4 N 0.33890(13) 0.3022(5) 0.56766(12) 0.0349(7) Uani 1 1 d . . . . .
O11 O 0.29750(13) 0.1883(5) 0.56073(15) 0.0633(9) Uani 1 1 d . . . . .
N3 N 0.66074(13) 0.1884(5) 0.67973(13) 0.0387(7) Uani 1 1 d . . . . .
N1 N 0.71812(13) 0.3949(5) 0.55790(13) 0.0432(8) Uani 1 1 d . . . . .
H1 H 0.753046 0.426716 0.562272 0.052 Uiso 1 1 calc R U . . .
N2 N 0.28070(14) 0.1021(6) 0.69018(15) 0.0497(9) Uani 1 1 d . . . . .
H2 H 0.245690 0.072147 0.686024 0.060 Uiso 1 1 calc R U . . .
C6 C 0.39325(15) 0.1968(5) 0.70227(13) 0.0292(7) Uani 1 1 d . . . . .
C3 C 0.60549(15) 0.2923(5) 0.54520(13) 0.0289(7) Uani 1 1 d . . . . .
C2 C 0.62608(16) 0.4994(6) 0.55541(15) 0.0384(9) Uani 1 1 d . . . . .
H2C H 0.601377 0.605548 0.558188 0.046 Uiso 1 1 calc R U . . .
C10 C 0.37321(17) -0.0099(6) 0.69645(18) 0.0457(10) Uani 1 1 d . . . . .
H10 H 0.398004 -0.119106 0.696352 0.055 Uiso 1 1 calc R U . . .
C1 C 0.68100(17) 0.5445(6) 0.56116(17) 0.0440(9) Uani 1 1 d . . . . .
H1C H 0.693410 0.681639 0.567492 0.053 Uiso 1 1 calc R U . . .
C7 C 0.35234(17) 0.3524(6) 0.70193(18) 0.0465(10) Uani 1 1 d . . . . .
H7 H 0.363199 0.491724 0.705959 0.056 Uiso 1 1 calc R U . . .
C4 C 0.64668(17) 0.1410(6) 0.54128(16) 0.0429(9) Uani 1 1 d . . . . .
H4 H 0.635874 0.002652 0.534086 0.052 Uiso 1 1 calc R U . . .
C5 C 0.70116(18) 0.1966(7) 0.54790(18) 0.0485(10) Uani 1 1 d . . . . .
H5 H 0.727343 0.095458 0.545474 0.058 Uiso 1 1 calc R U . . .
C9 C 0.31805(18) -0.0500(7) 0.6910(2) 0.0551(12) Uani 1 1 d . . . . .
H9 H 0.305656 -0.187728 0.687703 0.066 Uiso 1 1 calc R U . . .
C8 C 0.29777(19) 0.3006(7) 0.69581(19) 0.0539(11) Uani 1 1 d . . . . .
H8 H 0.271551 0.405219 0.695512 0.065 Uiso 1 1 calc R U . . .
H6A H 0.510(2) 0.385(9) 0.575(2) 0.086(19) Uiso 1 1 d . . . . .
H1B H 0.4680(19) 0.514(8) 0.6977(17) 0.058(14) Uiso 1 1 d . . . . .
H4A H 0.5006(15) 0.825(5) 0.5318(14) 0.018(9) Uiso 1 1 d . . . . .
H4B H 0.5297(19) 0.983(8) 0.5543(16) 0.053(13) Uiso 1 1 d . . . . .
H6B H 0.460(2) 0.391(7) 0.5837(17) 0.046(13) Uiso 1 1 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
Mg1 O6 2.046(3) . ?
Mg1 O1 2.071(3) . ?
Mg1 O3 2.032(3) . ?
Mg1 O4 2.080(3) . ?
Mg1 O5 2.058(3) . ?
Mg1 O2 2.065(3) . ?
O8 C6 1.281(4) . ?
O6 H6A 0.89(6) . ?
O6 H6B 0.78(5) . ?
O1 H1A 0.8540 . ?
O1 H1B 0.82(5) . ?
O3 H3A 0.8508 . ?
O3 H3B 0.8496 . ?
O7 C3 1.280(4) . ?
O4 H4A 0.78(3) . ?
O4 H4B 0.89(5) . ?
O5 H5A 0.8501 . ?
O5 H5B 0.8501 . ?
O2 H2A 0.8499 . ?
O2 H2B 0.8502 . ?
O9 N4 1.259(4) . ?
O10 N4 1.242(4) . ?
O13 N3 1.251(4) . ?
O12 N3 1.250(4) . ?
O14 N3 1.220(4) . ?
N4 O11 1.225(4) . ?
N1 H1 0.8600 . ?
N1 C1 1.345(5) . ?
N1 C5 1.340(5) . ?
N2 H2 0.8600 . ?
N2 C9 1.337(5) . ?
N2 C8 1.335(6) . ?
C6 C10 1.407(5) . ?
C6 C7 1.417(5) . ?
C3 C2 1.419(5) . ?
C3 C4 1.429(5) . ?
C2 H2C 0.9300 . ?
C2 C1 1.350(5) . ?
C10 H10 0.9300 . ?
C10 C9 1.351(6) . ?
C1 H1C 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.350(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.351(6) . ?
C5 H5 0.9300 . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?

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
O6 Mg1 O1 92.78(12) . . ?
O6 Mg1 O4 87.02(12) . . ?
O6 Mg1 O5 91.99(12) . . ?
O6 Mg1 O2 88.54(12) . . ?
O1 Mg1 O4 179.67(14) . . ?
O3 Mg1 O6 178.43(14) . . ?
O3 Mg1 O1 88.79(12) . . ?
O3 Mg1 O4 91.41(12) . . ?
O3 Mg1 O5 88.14(12) . . ?
O3 Mg1 O2 91.33(12) . . ?
O5 Mg1 O1 90.43(12) . . ?
O5 Mg1 O4 89.32(13) . . ?
O5 Mg1 O2 179.47(13) . . ?
O2 Mg1 O1 89.62(13) . . ?
O2 Mg1 O4 90.63(12) . . ?
Mg1 O6 H6A 130(4) . . ?
Mg1 O6 H6B 125(3) . . ?
H6A O6 H6B 104(5) . . ?
Mg1 O1 H1A 109.7 . . ?
Mg1 O1 H1B 129(3) . . ?
H1A O1 H1B 110.7 . . ?
Mg1 O3 H3A 127.5 . . ?
Mg1 O3 H3B 128.0 . . ?
H3A O3 H3B 104.5 . . ?
Mg1 O4 H4A 120(3) . . ?
Mg1 O4 H4B 127(3) . . ?
H4A O4 H4B 100(4) . . ?
Mg1 O5 H5A 127.4 . . ?
Mg1 O5 H5B 128.0 . . ?
H5A O5 H5B 104.5 . . ?
Mg1 O2 H2A 127.3 . . ?
Mg1 O2 H2B 128.1 . . ?
H2A O2 H2B 104.5 . . ?
O10 N4 O9 119.4(3) . . ?
O11 N4 O9 119.7(3) . . ?
O11 N4 O10 120.9(3) . . ?
O12 N3 O13 118.8(3) . . ?
O14 N3 O13 120.4(4) . . ?
O14 N3 O12 120.8(3) . . ?
C1 N1 H1 119.7 . . ?
C5 N1 H1 119.7 . . ?
C5 N1 C1 120.6(3) . . ?
C9 N2 H2 120.0 . . ?
C8 N2 H2 120.0 . . ?
C8 N2 C9 120.0(4) . . ?
O8 C6 C10 122.2(3) . . ?
O8 C6 C7 122.0(3) . . ?
C10 C6 C7 115.8(3) . . ?
O7 C3 C2 122.1(3) . . ?
O7 C3 C4 122.7(3) . . ?
C2 C3 C4 115.2(3) . . ?
C3 C2 H2C 119.5 . . ?
C1 C2 C3 121.0(4) . . ?
C1 C2 H2C 119.5 . . ?
C6 C10 H10 119.9 . . ?
C9 C10 C6 120.2(4) . . ?
C9 C10 H10 119.9 . . ?
N1 C1 C2 121.2(4) . . ?
N1 C1 H1C 119.4 . . ?
C2 C1 H1C 119.4 . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.7(4) . . ?
C8 C7 H7 119.6 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(4) . . ?
C5 C4 H4 119.6 . . ?
N1 C5 C4 121.2(4) . . ?
N1 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
N2 C9 C10 122.0(4) . . ?
N2 C9 H9 119.0 . . ?
C10 C9 H9 119.0 . . ?
N2 C8 C7 121.3(4) . . ?
N2 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?

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
_geom_hbond_publ_flag
O1 H1A O8 0.85 1.95 2.794(4) 168.0 4_556 yes
O3 H3A O8 0.85 1.86 2.709(4) 174.5 1_565 yes
O3 H3B O12 0.85 1.95 2.799(4) 173.8 1_565 yes
O5 H5A O12 0.85 1.96 2.782(4) 162.0 . yes
O5 H5B O13 0.85 1.96 2.800(4) 169.7 1_565 yes
O2 H2A O9 0.85 1.93 2.774(4) 171.0 . yes
O2 H2B O10 0.85 2.00 2.825(4) 163.3 1_565 yes
N1 H1 O9 0.86 1.99 2.846(4) 179.0 6_665 yes
N2 H2 O13 0.86 1.94 2.800(4) 179.5 6 yes
O6 H6A O7 0.89(6) 1.83(6) 2.717(4) 177(5) . yes
O1 H1B O8 0.82(5) 1.88(5) 2.690(3) 173(5) . yes
O4 H4A O7 0.78(3) 2.03(4) 2.809(4) 177(3) 5_666 yes
O4 H4B O7 0.89(5) 1.85(5) 2.742(4) 176(4) 1_565 yes
O6 H6B O10 0.78(5) 2.03(5) 2.816(4) 176(4) . yes

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
O8 C6 C10 C9 179.5(4) . . . . ?
O8 C6 C7 C8 179.9(4) . . . . ?
O7 C3 C2 C1 179.0(4) . . . . ?
O7 C3 C4 C5 -178.5(4) . . . . ?
C6 C10 C9 N2 0.9(7) . . . . ?
C6 C7 C8 N2 0.3(7) . . . . ?
C3 C2 C1 N1 -0.6(6) . . . . ?
C3 C4 C5 N1 -0.5(7) . . . . ?
C2 C3 C4 C5 1.0(6) . . . . ?
C10 C6 C7 C8 -0.6(6) . . . . ?
C1 N1 C5 C4 -0.6(6) . . . . ?
C7 C6 C10 C9 0.0(6) . . . . ?
C4 C3 C2 C1 -0.4(5) . . . . ?
C5 N1 C1 C2 1.2(6) . . . . ?
C9 N2 C8 C7 0.6(7) . . . . ?
C8 N2 C9 C10 -1.2(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2346368'
loop_
_audit_author_name
_audit_author_address
'Yang Li'
;Sogang University
South Korea
;
_audit_update_record             
;
2024-04-08 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2024-04-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H14 Li2 N4 O10'
_chemical_formula_sum            'C10 H14 Li2 N4 O10'
_chemical_formula_weight         364.13
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.821(8)
_cell_length_b                   10.477(9)
_cell_length_c                   9.205(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.89(3)
_cell_angle_gamma                90
_cell_volume                     794.8(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2793
_cell_measurement_temperature    171.00
_cell_measurement_theta_max      27.049
_cell_measurement_theta_min      3.064
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1416 before and 0.1095 after correction.
The Ratio of minimum to maximum transmission is 0.6001.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.098
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1264
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14271
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.747
_diffrn_ambient_temperature      171.00
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'PHOTON II CPAD detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1235
_reflns_number_total             1823
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.028(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1823
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0535
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0451P)²+0.3964P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1307
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 Li1-H2A \\sim Li1-H2B
 with sigma of 0.02
3.a Free rotating group:
 O2(H2A,H2B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C4(H4), C2(H2), C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1 O 0.90477(19) 0.53814(16) 0.35722(17) 0.0289(4) Uani 1 1 d . . . . .
O3 O 0.76032(19) 0.37449(15) 0.63469(18) 0.0309(4) Uani 1 1 d . . . . .
O2 O 0.8024(2) 0.67151(16) 0.63066(19) 0.0334(5) Uani 1 1 d G . . . .
H2A H 0.702690 0.698658 0.594021 0.050 Uiso 1 1 d DG U . . .
H2B H 0.842520 0.704810 0.723140 0.050 Uiso 1 1 d DG U . . .
O5 O 0.5280(2) 0.27913(16) 0.5495(2) 0.0380(5) Uani 1 1 d . . . . .
O4 O 0.5909(2) 0.42174(16) 0.40770(19) 0.0383(5) Uani 1 1 d . . . . .
N2 N 0.6250(2) 0.35839(17) 0.5295(2) 0.0239(4) Uani 1 1 d . . . . .
N1 N 0.6097(3) 0.60387(19) -0.0873(2) 0.0322(5) Uani 1 1 d . . . . .
H1 H 0.545061 0.617246 -0.183928 0.039 Uiso 1 1 calc R U . . .
C1 C 0.8122(3) 0.5596(2) 0.2175(2) 0.0224(5) Uani 1 1 d . . . . .
C5 C 0.8309(3) 0.4945(2) 0.0890(3) 0.0292(6) Uani 1 1 d . . . . .
H5 H 0.915296 0.433391 0.107101 0.035 Uiso 1 1 calc R U . . .
C4 C 0.7309(3) 0.5182(2) -0.0576(3) 0.0340(6) Uani 1 1 d . . . . .
H4 H 0.746085 0.473894 -0.141469 0.041 Uiso 1 1 calc R U . . .
C2 C 0.6820(3) 0.6491(2) 0.1784(3) 0.0291(6) Uani 1 1 d . . . . .
H2 H 0.662346 0.695282 0.258691 0.035 Uiso 1 1 calc R U . . .
C3 C 0.5860(3) 0.6693(2) 0.0285(3) 0.0335(6) Uani 1 1 d . . . . .
H3 H 0.500896 0.730254 0.004921 0.040 Uiso 1 1 calc R U . . .
Li1 Li 0.8704(5) 0.5170(4) 0.5526(4) 0.0284(9) Uani 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
O1 C1 1.274(3) . ?
O1 Li1 1.945(5) 3_766 ?
O1 Li1 1.940(4) . ?
O3 N2 1.252(3) . ?
O3 Li1 2.065(4) . ?
O2 H2A 0.8701 . ?
O2 H2B 0.8700 . ?
O2 Li1 1.950(4) . ?
O5 N2 1.253(3) . ?
O4 N2 1.244(2) . ?
O4 Li1 2.551(5) . ?
N2 Li1 2.676(5) . ?
N1 H1 0.8800 . ?
N1 C4 1.347(3) . ?
N1 C3 1.345(3) . ?
C1 C5 1.425(3) . ?
C1 C2 1.426(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.347(3) . ?
C4 H4 0.9500 . ?
C2 H2 0.9500 . ?
C2 C3 1.353(3) . ?
C3 H3 0.9500 . ?
Li1 Li1 2.805(8) 3_766 ?

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 O1 Li1 134.44(19) . . ?
C1 O1 Li1 132.27(18) . 3_766 ?
Li1 O1 Li1 92.46(18) . 3_766 ?
N2 O3 Li1 104.90(17) . . ?
H2A O2 H2B 104.5 . . ?
Li1 O2 H2A 122.0 . . ?
Li1 O2 H2B 128.5 . . ?
N2 O4 Li1 81.90(16) . . ?
O3 N2 O5 119.23(19) . . ?
O3 N2 Li1 48.23(13) . . ?
O5 N2 Li1 167.33(17) . . ?
O4 N2 O3 118.90(19) . . ?
O4 N2 O5 121.9(2) . . ?
O4 N2 Li1 70.70(15) . . ?
C4 N1 H1 119.5 . . ?
C3 N1 H1 119.5 . . ?
C3 N1 C4 121.0(2) . . ?
O1 C1 C5 122.1(2) . . ?
O1 C1 C2 122.7(2) . . ?
C5 C1 C2 115.2(2) . . ?
C1 C5 H5 119.5 . . ?
C4 C5 C1 121.0(2) . . ?
C4 C5 H5 119.5 . . ?
N1 C4 H4 119.5 . . ?
C5 C4 N1 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.0(2) . . ?
C3 C2 H2 119.5 . . ?
N1 C3 C2 120.7(2) . . ?
N1 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
O1 Li1 O1 87.54(18) . 3_766 ?
O1 Li1 O3 99.79(19) 3_766 . ?
O1 Li1 O3 132.1(2) . . ?
O1 Li1 O2 119.3(2) 3_766 . ?
O1 Li1 O2 114.6(2) . . ?
O1 Li1 O4 139.1(2) 3_766 . ?
O1 Li1 O4 90.07(16) . . ?
O1 Li1 N2 112.73(18) . . ?
O1 Li1 N2 121.49(19) 3_766 . ?
O1 Li1 Li1 43.71(13) 3_766 3_766 ?
O1 Li1 Li1 43.83(12) . 3_766 ?
O3 Li1 O4 54.25(12) . . ?
O3 Li1 N2 26.87(8) . . ?
O3 Li1 Li1 125.6(2) . 3_766 ?
O2 Li1 O3 102.64(19) . . ?
O2 Li1 O4 98.65(18) . . ?
O2 Li1 N2 101.45(18) . . ?
O2 Li1 Li1 128.9(3) . 3_766 ?
O4 Li1 N2 27.40(7) . . ?
O4 Li1 Li1 121.6(2) . 3_766 ?
N2 Li1 Li1 129.0(2) . 3_766 ?

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
_geom_hbond_publ_flag
O2 H2A O5 0.87 2.01 2.840(3) 160.3 3_666 yes
O2 H2B O5 0.87 2.14 3.006(3) 172.4 2_656 yes
N1 H1 O4 0.88 2.02 2.860(4) 158.9 3_665 yes

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
O1 C1 C5 C4 179.6(2) . . . . ?
O1 C1 C2 C3 -179.9(2) . . . . ?
C1 C5 C4 N1 -0.3(4) . . . . ?
C1 C2 C3 N1 0.9(4) . . . . ?
C5 C1 C2 C3 -0.4(3) . . . . ?
C4 N1 C3 C2 -1.1(4) . . . . ?
C2 C1 C5 C4 0.1(3) . . . . ?
C3 N1 C4 C5 0.7(4) . . . . ?
Li1 O1 C1 C5 29.1(4) 3_766 . . . ?
Li1 O1 C1 C5 -137.4(3) . . . . ?
Li1 O1 C1 C2 -151.4(2) 3_766 . . . ?
Li1 O1 C1 C2 42.0(4) . . . . ?
Li1 O3 N2 O5 -177.73(18) . . . . ?
Li1 O3 N2 O4 2.3(2) . . . . ?
Li1 O4 N2 O3 -1.82(19) . . . . ?
Li1 O4 N2 O5 178.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2346369'
loop_
_audit_author_name
_audit_author_address
'Yang Li'
;Sogang University
South Korea
;
_audit_update_record             
;
2024-04-08 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT911_2                   
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         14 Report
RESPONSE: There were omitted due to their Error/esd large than 9
;
_vrf_PLAT913_2                   
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....          8 Note
RESPONSE: There were omitted due to their Error/esd large than 9
;
# Added during the CSD deposition process: Monday 08 April 2024 01:16 AM
# end Validation Reply Form

_audit_creation_date             2024-04-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H14 Li2 N4 O10, 2(C5 H5 N O)'
_chemical_formula_sum            'C20 H24 Li2 N6 O12'
_chemical_formula_weight         554.33
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2120(6)
_cell_length_b                   8.9624(6)
_cell_length_c                   9.9320(7)
_cell_angle_alpha                82.101(2)
_cell_angle_beta                 68.227(2)
_cell_angle_gamma                70.184(2)
_cell_volume                     638.59(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    8708
_cell_measurement_temperature    140
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.81
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1055 before and 0.0893 after correction.
The Ratio of minimum to maximum transmission is 0.7494.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             288
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 -1.00 0.0730
0.00 1.00 1.00 0.1490
0.00 1.00 -1.00 0.1030
-1.00 1.00 0.00 0.1360
1.00 0.00 -1.00 0.0780
1.00 0.00 0.00 0.1010
-1.00 0.00 0.00 0.1240
1.00 0.00 1.00 0.1470
-1.00 0.00 -1.00 0.1110
1.00 1.00 -1.00 0.0850
-1.00 -1.00 1.00 0.0530
0.00 0.00 -1.00 0.0810
0.00 0.00 1.00 0.1130
0.00 1.00 0.00 0.1440
0.00 -1.00 0.00 0.0590
-1.00 1.00 1.00 0.1350
1.00 -1.00 -1.00 0.0800
1.00 1.00 0.00 0.1050
-1.00 -1.00 -1.00 0.0620
1.00 1.00 1.00 0.1050

_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.178
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14595
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.317
_diffrn_reflns_theta_min         2.416
_diffrn_ambient_temperature      140
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2802
_reflns_number_total             3158
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3158
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0634P)²+0.1873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1127
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 Li1-H6A \\sim Li1-H6B
 with sigma of 0.02
3.a Free rotating group:
 O6(H6A,H6B)
3.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N2(H2A), C6(H6), C5(H5), C3(H3), C11(H11), C9(H9), C8(H8), C7(H7),
 C2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O5 O 0.80197(13) 0.35259(12) 0.35094(11) 0.0297(2) Uani 1 1 d . . . . .
O6 O 1.00862(14) 0.16930(10) 0.07298(10) 0.0258(2) Uani 1 1 d G . . . .
H6A H 0.953665 0.104479 0.129638 0.039 Uiso 1 1 d DG U . . .
H6B H 1.026425 0.144261 -0.014062 0.039 Uiso 1 1 d DG U . . .
O2 O 0.89818(11) -0.08373(10) 0.21526(9) 0.02087(19) Uani 1 1 d . . . . .
O1 O 0.81610(11) 0.54992(10) 0.03903(9) 0.01951(19) Uani 1 1 d . . . . .
O7 O 0.95669(13) 0.21528(13) 0.48617(10) 0.0323(2) Uani 1 1 d . . . . .
O3 O 1.08853(13) 0.33392(12) 0.28984(10) 0.0299(2) Uani 1 1 d . . . . .
N3 N 0.94939(14) 0.30077(12) 0.37710(10) 0.0199(2) Uani 1 1 d . . . . .
N4 N 0.25572(13) 0.72844(12) 0.17353(11) 0.0211(2) Uani 1 1 d . . . . .
H4 H 0.134562 0.768255 0.204093 0.025 Uiso 1 1 calc R U . . .
N2 N 0.39601(14) -0.14835(13) 0.41845(11) 0.0236(2) Uani 1 1 d . . . . .
H2A H 0.287740 -0.163708 0.459631 0.028 Uiso 1 1 calc R U . . .
C6 C 0.57179(16) 0.02004(13) 0.29203(12) 0.0196(2) Uani 1 1 d . . . . .
H6 H 0.575823 0.121529 0.251099 0.024 Uiso 1 1 calc R U . . .
C5 C 0.54824(15) 0.75770(13) 0.03373(12) 0.0188(2) Uani 1 1 d . . . . .
H5 H 0.618132 0.820162 -0.031178 0.023 Uiso 1 1 calc R U . . .
C3 C 0.33610(16) 0.58170(15) 0.21797(13) 0.0211(2) Uani 1 1 d . . . . .
H3 H 0.260806 0.522074 0.280657 0.025 Uiso 1 1 calc R U . . .
C11 C 0.36002(16) 0.81444(14) 0.08252(13) 0.0208(2) Uani 1 1 d . . . . .
H11 H 0.300867 0.916857 0.051770 0.025 Uiso 1 1 calc R U . . .
C9 C 0.72111(16) -0.24988(14) 0.35154(13) 0.0205(2) Uani 1 1 d . . . . .
H9 H 0.827799 -0.335317 0.352305 0.025 Uiso 1 1 calc R U . . .
C10 C 0.74009(15) -0.10322(13) 0.28289(11) 0.0158(2) Uani 1 1 d . . . . .
C8 C 0.55093(17) -0.26820(15) 0.41602(13) 0.0229(3) Uani 1 1 d . . . . .
H8 H 0.540723 -0.367162 0.460227 0.028 Uiso 1 1 calc R U . . .
C7 C 0.40539(16) -0.00562(15) 0.35856(13) 0.0228(2) Uani 1 1 d . . . . .
H7 H 0.295047 0.077752 0.362785 0.027 Uiso 1 1 calc R U . . .
C2 C 0.52351(16) 0.51789(13) 0.17428(12) 0.0186(2) Uani 1 1 d . . . . .
H2 H 0.576938 0.414571 0.206899 0.022 Uiso 1 1 calc R U . . .
C1 C 0.64087(15) 0.60491(13) 0.07969(11) 0.0156(2) Uani 1 1 d . . . . .
Li1 Li 0.9869(3) 0.3823(2) 0.1118(2) 0.0200(4) Uani 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
O5 N3 1.2521(13) . ?
O5 Li1 2.333(2) . ?
O6 H6A 0.8702 . ?
O6 H6B 0.8697 . ?
O6 Li1 1.935(2) . ?
O2 C10 1.2813(13) . ?
O1 C1 1.2726(13) . ?
O1 Li1 1.942(2) . ?
O1 Li1 1.962(2) 2_765 ?
O7 N3 1.2462(13) . ?
O3 N3 1.2529(13) . ?
O3 Li1 2.157(2) . ?
N3 Li1 2.568(2) . ?
N4 H4 0.8800 . ?
N4 C3 1.3521(16) . ?
N4 C11 1.3515(15) . ?
N2 H2A 0.8800 . ?
N2 C8 1.3530(17) . ?
N2 C7 1.3490(17) . ?
C6 H6 0.9500 . ?
C6 C10 1.4276(15) . ?
C6 C7 1.3632(16) . ?
C5 H5 0.9500 . ?
C5 C11 1.3644(15) . ?
C5 C1 1.4289(15) . ?
C3 H3 0.9500 . ?
C3 C2 1.3638(16) . ?
C11 H11 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.4249(15) . ?
C9 C8 1.3613(16) . ?
C8 H8 0.9500 . ?
C7 H7 0.9500 . ?
C2 H2 0.9500 . ?
C2 C1 1.4340(15) . ?
Li1 Li1 2.845(4) 2_765 ?

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
N3 O5 Li1 85.91(8) . . ?
H6A O6 H6B 104.5 . . ?
Li1 O6 H6A 128.7 . . ?
Li1 O6 H6B 119.9 . . ?
C1 O1 Li1 133.77(9) . . ?
C1 O1 Li1 132.47(9) . 2_765 ?
Li1 O1 Li1 93.57(8) . 2_765 ?
N3 O3 Li1 93.95(9) . . ?
O5 N3 O3 118.52(10) . . ?
O5 N3 Li1 64.99(8) . . ?
O7 N3 O5 120.07(10) . . ?
O7 N3 O3 121.40(10) . . ?
O7 N3 Li1 160.13(10) . . ?
O3 N3 Li1 56.92(7) . . ?
C3 N4 H4 119.7 . . ?
C11 N4 H4 119.7 . . ?
C11 N4 C3 120.51(10) . . ?
C8 N2 H2A 119.6 . . ?
C7 N2 H2A 119.6 . . ?
C7 N2 C8 120.85(10) . . ?
C10 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C7 C6 C10 121.03(11) . . ?
C11 C5 H5 119.8 . . ?
C11 C5 C1 120.40(10) . . ?
C1 C5 H5 119.8 . . ?
N4 C3 H3 119.5 . . ?
N4 C3 C2 121.07(11) . . ?
C2 C3 H3 119.5 . . ?
N4 C11 C5 121.59(11) . . ?
N4 C11 H11 119.2 . . ?
C5 C11 H11 119.2 . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.35(11) . . ?
O2 C10 C6 122.01(10) . . ?
O2 C10 C9 122.19(10) . . ?
C9 C10 C6 115.79(10) . . ?
N2 C8 C9 121.35(11) . . ?
N2 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
N2 C7 C6 120.59(11) . . ?
N2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C3 C2 H2 119.6 . . ?
C3 C2 C1 120.78(11) . . ?
C1 C2 H2 119.6 . . ?
O1 C1 C5 122.05(10) . . ?
O1 C1 C2 122.33(10) . . ?
C5 C1 C2 115.62(10) . . ?
O5 Li1 N3 29.10(4) . . ?
O5 Li1 Li1 139.64(12) . 2_765 ?
O6 Li1 O5 89.33(8) . . ?
O6 Li1 O1 114.87(11) . . ?
O6 Li1 O1 109.61(10) . 2_765 ?
O6 Li1 O3 99.86(9) . . ?
O6 Li1 N3 89.48(8) . . ?
O6 Li1 Li1 121.23(13) . 2_765 ?
O1 Li1 O5 102.04(9) . . ?
O1 Li1 O5 153.95(11) 2_765 . ?
O1 Li1 O1 86.43(8) . 2_765 ?
O1 Li1 O3 100.79(9) 2_765 . ?
O1 Li1 O3 139.89(11) . . ?
O1 Li1 N3 129.86(10) 2_765 . ?
O1 Li1 N3 127.72(10) . . ?
O1 Li1 Li1 43.49(6) . 2_765 ?
O1 Li1 Li1 42.94(6) 2_765 2_765 ?
O3 Li1 O5 57.14(6) . . ?
O3 Li1 N3 29.12(4) . . ?
O3 Li1 Li1 130.63(13) . 2_765 ?
N3 Li1 Li1 149.27(13) . 2_765 ?

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
_geom_hbond_publ_flag
O6 H6A O2 0.87 1.90 2.7432(12) 162.3 . yes
O6 H6B O2 0.87 1.96 2.8194(12) 172.2 2_755 yes
N4 H4 O2 0.88 1.92 2.7503(13) 157.4 1_465 yes
N2 H2A O5 0.88 2.43 3.0565(14) 128.8 2_656 yes
N2 H2A O7 0.88 2.07 2.9381(14) 168.0 2_656 yes

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
N4 C3 C2 C1 -0.01(18) . . . . ?
C3 N4 C11 C5 -0.65(18) . . . . ?
C3 C2 C1 O1 178.71(10) . . . . ?
C3 C2 C1 C5 -1.35(16) . . . . ?
C11 N4 C3 C2 1.06(18) . . . . ?
C11 C5 C1 O1 -178.32(11) . . . . ?
C11 C5 C1 C2 1.74(16) . . . . ?
C10 C6 C7 N2 0.50(18) . . . . ?
C10 C9 C8 N2 -0.81(18) . . . . ?
C8 N2 C7 C6 1.12(18) . . . . ?
C8 C9 C10 O2 -176.68(11) . . . . ?
C8 C9 C10 C6 2.28(16) . . . . ?
C7 N2 C8 C9 -0.97(18) . . . . ?
C7 C6 C10 O2 176.82(11) . . . . ?
C7 C6 C10 C9 -2.14(16) . . . . ?
C1 C5 C11 N4 -0.81(18) . . . . ?
Li1 O5 N3 O7 -158.29(12) . . . . ?
Li1 O5 N3 O3 20.12(11) . . . . ?
Li1 O1 C1 C5 -12.33(18) 2_765 . . . ?
Li1 O1 C1 C5 161.26(12) . . . . ?
Li1 O1 C1 C2 -18.81(19) . . . . ?
Li1 O1 C1 C2 167.61(12) 2_765 . . . ?
Li1 O3 N3 O5 -21.84(12) . . . . ?
Li1 O3 N3 O7 156.54(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
