# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2351403'
loop_
_audit_author_name
_audit_author_address
'Dechambenoit Pierre'
;University of Bordeaux
France
;
_audit_update_record             
;
2024-04-26 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 Li N2 O2'
_chemical_formula_sum            'C16 H20 Li N2 O2'
_chemical_formula_weight         279.28

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.5128(17)
_cell_length_b                   11.9757(7)
_cell_length_c                   20.7828(11)
_cell_angle_alpha                90
_cell_angle_beta                 118.145(3)
_cell_angle_gamma                90
_cell_volume                     6257.4(6)
_cell_formula_units_Z            16
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2092
_cell_measurement_theta_max      24.00
_cell_measurement_theta_min      2.94

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_F_000             2384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6388
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II Quasar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24998
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_av_R_equivalents  0.0810
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.620
_diffrn_reflns_theta_max         25.128
_diffrn_reflns_theta_full        25.128
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5572
_reflns_number_gt                2420
_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       'Bruker APEX2'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0866P)²+0.5243P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5572
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1583
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1930
_refine_ls_wR_factor_gt          0.1473
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
O4 O 0.81376(9) 0.9148(2) 0.81639(12) 0.0371(7) Uani 1 1 d . . . . .
O3 O 0.69404(9) 0.9222(2) 0.69382(12) 0.0421(8) Uani 1 1 d . . . . .
O2 O 0.56080(10) 0.8288(3) 0.31333(12) 0.0470(8) Uani 1 1 d . . . . .
O1 O 0.56031(11) 0.3313(3) 0.31148(13) 0.0495(9) Uani 1 1 d . . . . .
N3 N 0.76924(11) 1.0831(3) 0.67615(15) 0.0339(8) Uani 1 1 d . . . . .
N2 N 0.51358(11) 0.6614(3) 0.17522(15) 0.0351(8) Uani 1 1 d . . . . .
N4 N 0.74559(11) 1.1043(3) 0.82550(16) 0.0380(9) Uani 1 1 d . . . . .
N1 N 0.51124(12) 0.1516(3) 0.17689(17) 0.0430(9) Uani 1 1 d . . . . .
C19 C 0.75728(13) 1.1899(3) 0.56257(17) 0.0238(9) Uani 1 1 d . . . . .
C20 C 0.76419(12) 1.1315(3) 0.62500(18) 0.0267(9) Uani 1 1 d . . . . .
C12 C 0.51042(13) 0.6136(3) 0.12411(18) 0.0272(9) Uani 1 1 d . . . . .
C11 C 0.50550(13) 0.5571(3) 0.06239(17) 0.0237(9) Uani 1 1 d . . . . .
C32 C 0.74015(12) 1.3649(3) 0.99868(16) 0.0294(8) Uani 1 1 d . . . . .
H32 H 0.733251 1.442614 0.998090 0.035 Uiso 1 1 calc R U . . .
C29 C 0.74680(13) 1.1478(4) 0.87593(18) 0.0302(10) Uani 1 1 d . . . . .
C10 C 0.54358(13) 0.4761(3) 0.06757(16) 0.0303(8) Uani 1 1 d . . . . .
H10 H 0.573166 0.460591 0.113711 0.036 Uiso 1 1 calc R U . . .
C30 C 0.74853(13) 1.1995(4) 0.93785(17) 0.0276(10) Uani 1 1 d . . . . .
C9 C 0.53829(12) 0.4206(3) 0.00755(15) 0.0297(8) Uani 1 1 d . . . . .
H9 H 0.564016 0.366303 0.012214 0.036 Uiso 1 1 calc R U . . .
C31 C 0.73917(13) 1.3157(3) 0.93885(16) 0.0316(9) Uani 1 1 d . . . . .
H31 H 0.732131 1.359822 0.897281 0.038 Uiso 1 1 calc R U . . .
C17 C 0.70580(13) 1.2259(3) 0.43292(16) 0.0306(8) Uani 1 1 d . . . . .
H17 H 0.676043 1.209568 0.387113 0.037 Uiso 1 1 calc R U . . .
C4 C 0.50766(13) 0.1064(4) 0.12496(19) 0.0314(10) Uani 1 1 d . . . . .
C1 C 0.50745(12) -0.1160(3) 0.00141(16) 0.0308(8) Uani 1 1 d . . . . .
H1 H 0.512494 -0.194448 0.001761 0.037 Uiso 1 1 calc R U . . .
C18 C 0.71270(12) 1.1686(3) 0.49354(15) 0.0284(8) Uani 1 1 d . . . . .
H18 H 0.687383 1.113725 0.489519 0.034 Uiso 1 1 calc R U . . .
C3 C 0.50352(13) 0.0524(4) 0.06274(18) 0.0293(10) Uani 1 1 d . . . . .
C2 C 0.51067(12) -0.0645(3) 0.06164(16) 0.0322(9) Uani 1 1 d . . . . .
H2 H 0.517820 -0.107604 0.103655 0.039 Uiso 1 1 calc R U . . .
C15 C 0.61703(14) 0.9316(4) 0.41505(17) 0.0361(10) Uani 1 1 d . . . . .
H15A H 0.653667 0.929093 0.456159 0.043 Uiso 1 1 calc R U . . .
H15B H 0.593886 0.971602 0.430945 0.043 Uiso 1 1 calc R U . . .
C27 C 0.86572(14) 0.7931(4) 0.91346(18) 0.0379(11) Uani 1 1 d . . . . .
H27A H 0.859853 0.739327 0.945167 0.045 Uiso 1 1 calc R U . . .
H27B H 0.902594 0.821730 0.939809 0.045 Uiso 1 1 calc R U . . .
C14 C 0.61597(14) 0.9878(3) 0.34856(18) 0.0401(11) Uani 1 1 d . . . . .
H14A H 0.597997 1.061263 0.339194 0.048 Uiso 1 1 calc R U . . .
H14B H 0.652455 0.998475 0.355333 0.048 Uiso 1 1 calc R U . . .
C7 C 0.61336(14) 0.4555(4) 0.40601(18) 0.0373(10) Uani 1 1 d . . . . .
H7A H 0.607086 0.511911 0.435957 0.045 Uiso 1 1 calc R U . . .
H7B H 0.650230 0.427253 0.433649 0.045 Uiso 1 1 calc R U . . .
C22 C 0.63528(14) 0.8190(4) 0.59303(19) 0.0368(10) Uani 1 1 d . . . . .
H22A H 0.658171 0.780265 0.576151 0.044 Uiso 1 1 calc R U . . .
H22B H 0.598252 0.820134 0.552868 0.044 Uiso 1 1 calc R U . . .
C6 C 0.60335(15) 0.5043(4) 0.33331(18) 0.0435(11) Uani 1 1 d . . . . .
H6A H 0.575942 0.563549 0.317273 0.052 Uiso 1 1 calc R U . . .
H6B H 0.636416 0.535651 0.336214 0.052 Uiso 1 1 calc R U . . .
C8 C 0.57331(13) 0.3606(3) 0.38469(16) 0.0390(10) Uani 1 1 d . . . . .
H8A H 0.588990 0.295992 0.417686 0.047 Uiso 1 1 calc R U . . .
H8B H 0.541116 0.385134 0.387373 0.047 Uiso 1 1 calc R U . . .
C5 C 0.58449(16) 0.4070(4) 0.28307(19) 0.0448(12) Uani 1 1 d . . . . .
H5A H 0.558395 0.431290 0.233380 0.054 Uiso 1 1 calc R U . . .
H5B H 0.614741 0.370604 0.280501 0.054 Uiso 1 1 calc R U . . .
C16 C 0.59634(14) 0.8154(3) 0.38902(17) 0.0435(11) Uani 1 1 d . . . . .
H16A H 0.625750 0.764045 0.396751 0.052 Uiso 1 1 calc R U . . .
H16B H 0.577493 0.785709 0.414988 0.052 Uiso 1 1 calc R U . . .
C21 C 0.65513(13) 0.9352(3) 0.61895(16) 0.0415(10) Uani 1 1 d . . . . .
H21A H 0.671323 0.967916 0.590313 0.050 Uiso 1 1 calc R U . . .
H21B H 0.625735 0.984081 0.614443 0.050 Uiso 1 1 calc R U . . .
C25 C 0.83969(15) 0.8374(4) 0.79064(19) 0.0399(11) Uani 1 1 d . . . . .
H25A H 0.871621 0.871869 0.791742 0.048 Uiso 1 1 calc R U . . .
H25B H 0.815263 0.813965 0.739992 0.048 Uiso 1 1 calc R U . . .
C23 C 0.63845(14) 0.7631(4) 0.66078(19) 0.0402(11) Uani 1 1 d . . . . .
H23A H 0.602942 0.759734 0.658308 0.048 Uiso 1 1 calc R U . . .
H23B H 0.652784 0.686369 0.666323 0.048 Uiso 1 1 calc R U . . .
C26 C 0.85500(15) 0.7391(4) 0.84155(19) 0.0434(12) Uani 1 1 d . . . . .
H26A H 0.887206 0.701700 0.845470 0.052 Uiso 1 1 calc R U . . .
H26B H 0.825682 0.684165 0.825331 0.052 Uiso 1 1 calc R U . . .
C28 C 0.82595(14) 0.8873(3) 0.89047(16) 0.0387(10) Uani 1 1 d . . . . .
H28A H 0.793407 0.863526 0.892482 0.046 Uiso 1 1 calc R U . . .
H28B H 0.841291 0.952655 0.922886 0.046 Uiso 1 1 calc R U . . .
C13 C 0.5852(2) 0.9081(5) 0.2874(2) 0.090(2) Uani 1 1 d . . . . .
H13A H 0.557806 0.948676 0.244703 0.107 Uiso 1 1 calc R U . . .
H13B H 0.609326 0.869837 0.272441 0.107 Uiso 1 1 calc R U . . .
C24 C 0.6754(2) 0.8361(5) 0.7226(2) 0.089(2) Uani 1 1 d . . . . .
H24A H 0.656491 0.868635 0.747687 0.107 Uiso 1 1 calc R U . . .
H24B H 0.705771 0.791578 0.758502 0.107 Uiso 1 1 calc R U . . .
Li2 Li 0.500000 0.7406(8) 0.250000 0.031(2) Uani 1 2 d S T P . .
Li3 Li 0.7561(2) 1.0117(7) 0.7535(2) 0.0307(19) Uani 1 1 d . . . . .
Li1 Li 0.500000 0.2361(8) 0.250000 0.036(2) Uani 1 2 d S T P . .


_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
O4 C25 1.437(4) . ?
O4 C28 1.447(3) . ?
O4 Li3 1.931(7) . ?
O3 C24 1.415(5) . ?
O3 C21 1.431(4) . ?
O3 Li3 1.936(7) . ?
O2 C16 1.422(4) . ?
O2 C13 1.425(5) . ?
O2 Li2 1.924(6) . ?
O1 C5 1.424(5) . ?
O1 C8 1.430(4) . ?
O1 Li1 1.953(7) . ?
N3 C20 1.159(4) . ?
N3 Li3 2.005(6) . ?
N2 C12 1.172(4) . ?
N2 Li2 2.008(6) . ?
N4 C29 1.156(4) . ?
N4 Li3 1.996(7) . ?
N1 C4 1.168(4) . ?
N1 Li1 1.974(6) . ?
C19 C20 1.404(5) . ?
C19 C18 1.421(4) . ?
C19 C17 1.428(5) 7_676 ?
C12 C11 1.397(5) . ?
C11 C10 1.422(5) . ?
C11 C9 1.425(4) 5_665 ?
C32 C31 1.365(4) . ?
C32 C30 1.427(5) 7_677 ?
C32 H32 0.9500 . ?
C29 C30 1.408(5) . ?
C10 C9 1.358(4) . ?
C10 H10 0.9500 . ?
C30 C31 1.419(5) . ?
C9 H9 0.9500 . ?
C31 H31 0.9500 . ?
C17 C18 1.365(4) . ?
C17 H17 0.9500 . ?
C4 C3 1.400(5) . ?
C1 C2 1.359(4) . ?
C1 C3 1.436(5) 5_655 ?
C1 H1 0.9500 . ?
C18 H18 0.9500 . ?
C3 C2 1.417(5) . ?
C2 H2 0.9500 . ?
C15 C16 1.508(5) . ?
C15 C14 1.525(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C27 C28 1.509(5) . ?
C27 C26 1.521(5) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C14 C13 1.498(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C7 C6 1.516(5) . ?
C7 C8 1.521(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C22 C21 1.503(5) . ?
C22 C23 1.523(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C6 C5 1.486(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C25 C26 1.503(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C23 C24 1.500(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

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
C25 O4 C28 110.0(3) . . ?
C25 O4 Li3 123.9(3) . . ?
C28 O4 Li3 123.9(3) . . ?
C24 O3 C21 106.6(3) . . ?
C24 O3 Li3 123.0(3) . . ?
C21 O3 Li3 129.9(3) . . ?
C16 O2 C13 105.9(3) . . ?
C16 O2 Li2 129.5(3) . . ?
C13 O2 Li2 123.4(3) . . ?
C5 O1 C8 110.6(3) . . ?
C5 O1 Li1 123.3(2) . . ?
C8 O1 Li1 123.1(2) . . ?
C20 N3 Li3 163.6(3) . . ?
C12 N2 Li2 166.3(3) . . ?
C29 N4 Li3 168.3(3) . . ?
C4 N1 Li1 166.9(3) . . ?
C20 C19 C18 120.8(3) . . ?
C20 C19 C17 120.9(3) . 7_676 ?
C18 C19 C17 118.3(3) . 7_676 ?
N3 C20 C19 179.2(4) . . ?
N2 C12 C11 178.8(4) . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 C9 120.4(3) . 5_665 ?
C10 C11 C9 118.4(3) . 5_665 ?
C31 C32 C30 120.5(3) . 7_677 ?
C31 C32 H32 119.8 . . ?
C30 C32 H32 119.8 7_677 . ?
N4 C29 C30 179.2(5) . . ?
C9 C10 C11 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C29 C30 C31 121.2(3) . . ?
C29 C30 C32 120.2(4) . 7_677 ?
C31 C30 C32 118.6(3) . 7_677 ?
C10 C9 C11 120.6(3) . 5_665 ?
C10 C9 H9 119.7 . . ?
C11 C9 H9 119.7 5_665 . ?
C32 C31 C30 120.9(3) . . ?
C32 C31 H31 119.5 . . ?
C30 C31 H31 119.5 . . ?
C18 C17 C19 120.9(3) . 7_676 ?
C18 C17 H17 119.5 . . ?
C19 C17 H17 119.5 7_676 . ?
N1 C4 C3 179.8(5) . . ?
C2 C1 C3 120.3(3) . 5_655 ?
C2 C1 H1 119.8 . . ?
C3 C1 H1 119.8 5_655 . ?
C17 C18 C19 120.8(3) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 C1 120.0(4) . 5_655 ?
C2 C3 C1 118.6(3) . 5_655 ?
C1 C2 C3 121.0(3) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C16 C15 C14 104.2(3) . . ?
C16 C15 H15A 110.9 . . ?
C14 C15 H15A 110.9 . . ?
C16 C15 H15B 110.9 . . ?
C14 C15 H15B 110.9 . . ?
H15A C15 H15B 108.9 . . ?
C28 C27 C26 103.5(3) . . ?
C28 C27 H27A 111.1 . . ?
C26 C27 H27A 111.1 . . ?
C28 C27 H27B 111.1 . . ?
C26 C27 H27B 111.1 . . ?
H27A C27 H27B 109.0 . . ?
C13 C14 C15 103.9(3) . . ?
C13 C14 H14A 111.0 . . ?
C15 C14 H14A 111.0 . . ?
C13 C14 H14B 111.0 . . ?
C15 C14 H14B 111.0 . . ?
H14A C14 H14B 109.0 . . ?
C6 C7 C8 103.6(3) . . ?
C6 C7 H7A 111.0 . . ?
C8 C7 H7A 111.0 . . ?
C6 C7 H7B 111.0 . . ?
C8 C7 H7B 111.0 . . ?
H7A C7 H7B 109.0 . . ?
C21 C22 C23 103.1(3) . . ?
C21 C22 H22A 111.1 . . ?
C23 C22 H22A 111.1 . . ?
C21 C22 H22B 111.1 . . ?
C23 C22 H22B 111.1 . . ?
H22A C22 H22B 109.1 . . ?
C5 C6 C7 103.5(4) . . ?
C5 C6 H6A 111.1 . . ?
C7 C6 H6A 111.1 . . ?
C5 C6 H6B 111.1 . . ?
C7 C6 H6B 111.1 . . ?
H6A C6 H6B 109.0 . . ?
O1 C8 C7 106.0(3) . . ?
O1 C8 H8A 110.5 . . ?
C7 C8 H8A 110.5 . . ?
O1 C8 H8B 110.5 . . ?
C7 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
O1 C5 C6 107.0(3) . . ?
O1 C5 H5A 110.3 . . ?
C6 C5 H5A 110.3 . . ?
O1 C5 H5B 110.3 . . ?
C6 C5 H5B 110.3 . . ?
H5A C5 H5B 108.6 . . ?
O2 C16 C15 104.3(3) . . ?
O2 C16 H16A 110.9 . . ?
C15 C16 H16A 110.9 . . ?
O2 C16 H16B 110.9 . . ?
C15 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
O3 C21 C22 104.9(3) . . ?
O3 C21 H21A 110.8 . . ?
C22 C21 H21A 110.8 . . ?
O3 C21 H21B 110.8 . . ?
C22 C21 H21B 110.8 . . ?
H21A C21 H21B 108.8 . . ?
O4 C25 C26 105.8(3) . . ?
O4 C25 H25A 110.6 . . ?
C26 C25 H25A 110.6 . . ?
O4 C25 H25B 110.6 . . ?
C26 C25 H25B 110.6 . . ?
H25A C25 H25B 108.7 . . ?
C24 C23 C22 104.3(3) . . ?
C24 C23 H23A 110.9 . . ?
C22 C23 H23A 110.9 . . ?
C24 C23 H23B 110.9 . . ?
C22 C23 H23B 110.9 . . ?
H23A C23 H23B 108.9 . . ?
C25 C26 C27 102.5(3) . . ?
C25 C26 H26A 111.3 . . ?
C27 C26 H26A 111.3 . . ?
C25 C26 H26B 111.3 . . ?
C27 C26 H26B 111.3 . . ?
H26A C26 H26B 109.2 . . ?
O4 C28 C27 106.0(3) . . ?
O4 C28 H28A 110.5 . . ?
C27 C28 H28A 110.5 . . ?
O4 C28 H28B 110.5 . . ?
C27 C28 H28B 110.5 . . ?
H28A C28 H28B 108.7 . . ?
O2 C13 C14 107.4(3) . . ?
O2 C13 H13A 110.2 . . ?
C14 C13 H13A 110.2 . . ?
O2 C13 H13B 110.2 . . ?
C14 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
O3 C24 C23 108.3(3) . . ?
O3 C24 H24A 110.0 . . ?
C23 C24 H24A 110.0 . . ?
O3 C24 H24B 110.0 . . ?
C23 C24 H24B 110.0 . . ?
H24A C24 H24B 108.4 . . ?
O2 Li2 O2 113.4(5) 2_655 . ?
O2 Li2 N2 110.39(13) 2_655 2_655 ?
O2 Li2 N2 99.82(11) . 2_655 ?
O2 Li2 N2 99.82(11) 2_655 . ?
O2 Li2 N2 110.39(12) . . ?
N2 Li2 N2 123.6(5) 2_655 . ?
O4 Li3 O3 109.2(4) . . ?
O4 Li3 N4 101.9(2) . . ?
O3 Li3 N4 111.9(3) . . ?
O4 Li3 N3 112.2(3) . . ?
O3 Li3 N3 100.5(2) . . ?
N4 Li3 N3 121.0(4) . . ?
O1 Li1 O1 108.6(5) 2_655 . ?
O1 Li1 N1 102.02(12) 2_655 . ?
O1 Li1 N1 112.98(13) . . ?
O1 Li1 N1 112.98(13) 2_655 2_655 ?
O1 Li1 N1 102.02(12) . 2_655 ?
N1 Li1 N1 118.3(5) . 2_655 ?

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.046



_chemical_properties_physical    Moisture-sensitive
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2351404'
loop_
_audit_author_name
_audit_author_address
'Dechambenoit Pierre'
;University of Bordeaux
France
;
_audit_update_record             
;
2025-05-26 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 Li N2 O2'

_chemical_formula_sum            'C16 H20 Li N2 O2'
_chemical_formula_weight         279.28

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.939(4)
_cell_length_b                   5.9609(16)
_cell_length_c                   18.837(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.844(15)
_cell_angle_gamma                90
_cell_volume                     1641.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    1518
_cell_measurement_theta_max      24.12
_cell_measurement_theta_min      2.79

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.130
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6433
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II Quasar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5322
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.786
_diffrn_reflns_theta_max         24.146
_diffrn_reflns_theta_full        24.146
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             1281
_reflns_number_gt                811
_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       'Bruker APEX2'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
All non-hydrogens were refined anisotropically. Hydrogen atoms were assigned to ideal positions and refined isotropically using a riding model.
;
_vrf_THETM01_shelx               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.590
Calculated sin(theta_max)/wavelength = 0.5756
RESPONSE: At 250 K, the data were cut at 0.87 Angstrom as 
there is no diffraction below.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1501P)²+0.5316P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1281
_refine_ls_number_parameters     96
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1224
_refine_ls_R_factor_gt           0.0703
_refine_ls_wR_factor_ref         0.2597
_refine_ls_wR_factor_gt          0.2259
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_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
O1 O 0.55599(18) 0.3592(4) 0.68729(11) 0.0813(10) Uani 1 1 d . . . . .
N1 N 0.4056(2) 0.0081(5) 0.67727(15) 0.0808(11) Uani 1 1 d . . . . .
C2 C 0.2916(3) -0.0457(6) 0.49693(18) 0.0739(12) Uani 1 1 d . . . . .
H2 H 0.320192 0.093787 0.494543 0.089 Uiso 1 1 calc R U . . .
C3 C 0.3061(2) -0.1615(5) 0.56304(15) 0.0546(9) Uani 1 1 d . . . . .
C4 C 0.3606(2) -0.0698(6) 0.62568(17) 0.0631(10) Uani 1 1 d . . . . .
C5 C 0.5266(4) 0.3925(9) 0.6120(2) 0.1073(18) Uani 1 1 d . . . . .
H5A H 0.460129 0.413953 0.600044 0.129 Uiso 1 1 calc R U . . .
H5B H 0.541647 0.260883 0.585581 0.129 Uiso 1 1 calc R U . . .
C6 C 0.5727(3) 0.5917(8) 0.5911(2) 0.0931(14) Uani 1 1 d . . . . .
H6A H 0.528001 0.707411 0.571087 0.112 Uiso 1 1 calc R U . . .
H6B H 0.608495 0.553229 0.554675 0.112 Uiso 1 1 calc R U . . .
C7 C 0.6340(3) 0.6725(9) 0.6596(2) 0.0996(15) Uani 1 1 d . . . . .
H7A H 0.696055 0.698893 0.651869 0.119 Uiso 1 1 calc R U . . .
H7B H 0.610557 0.812167 0.676284 0.119 Uiso 1 1 calc R U . . .
C1 C 0.2377(3) -0.1300(6) 0.43684(17) 0.0808(13) Uani 1 1 d . . . . .
H1 H 0.229159 -0.047138 0.393518 0.097 Uiso 1 1 calc R U . . .
C8 C 0.6337(4) 0.4950(10) 0.7116(3) 0.129(2) Uani 1 1 d . . . . .
H8A H 0.689468 0.404889 0.716319 0.155 Uiso 1 1 calc R U . . .
H8B H 0.631704 0.558839 0.759221 0.155 Uiso 1 1 calc R U . . .
Li1 Li 0.500000 0.1695(13) 0.750000 0.061(2) Uani 1 2 d S T P . .


_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 C5 1.410(4) . ?
O1 C8 1.412(5) . ?
O1 Li1 1.944(5) . ?
N1 C4 1.160(4) . ?
N1 Li1 1.999(5) . ?
C2 C1 1.345(4) . ?
C2 C3 1.401(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.400(4) . ?
C3 C1 1.405(5) 7_546 ?
C5 C6 1.467(6) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C6 C7 1.500(6) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 C8 1.443(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C1 H1 0.9400 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?

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
C5 O1 C8 108.2(3) . . ?
C5 O1 Li1 127.5(2) . . ?
C8 O1 Li1 124.3(2) . . ?
C4 N1 Li1 166.7(3) . . ?
C1 C2 C3 121.4(3) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 C1 122.3(3) . 7_546 ?
C2 C3 C1 116.7(3) . 7_546 ?
N1 C4 C3 179.4(4) . . ?
O1 C5 C6 108.5(3) . . ?
O1 C5 H5A 110.0 . . ?
C6 C5 H5A 110.0 . . ?
O1 C5 H5B 110.0 . . ?
C6 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
C5 C6 C7 105.5(3) . . ?
C5 C6 H6A 110.6 . . ?
C7 C6 H6A 110.6 . . ?
C5 C6 H6B 110.6 . . ?
C7 C6 H6B 110.6 . . ?
H6A C6 H6B 108.8 . . ?
C8 C7 C6 105.2(4) . . ?
C8 C7 H7A 110.7 . . ?
C6 C7 H7A 110.7 . . ?
C8 C7 H7B 110.7 . . ?
C6 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
C2 C1 C3 121.9(3) . 7_546 ?
C2 C1 H1 119.1 . . ?
C3 C1 H1 119.1 7_546 . ?
O1 C8 C7 108.5(3) . . ?
O1 C8 H8A 110.0 . . ?
C7 C8 H8A 110.0 . . ?
O1 C8 H8B 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
O1 Li1 O1 108.8(4) 2_656 . ?
O1 Li1 N1 101.21(11) 2_656 2_656 ?
O1 Li1 N1 111.44(13) . 2_656 ?
O1 Li1 N1 111.44(13) 2_656 . ?
O1 Li1 N1 101.21(11) . . ?
N1 Li1 N1 122.5(4) 2_656 . ?

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.063



_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2351405'
loop_
_audit_author_name
_audit_author_address
'Dechambenoit Pierre'
;University of Bordeaux
France
;
_audit_update_record             
;
2025-05-26 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 N2 Na O'
_chemical_formula_sum            'C12 H12 N2 Na O'
_chemical_formula_weight         223.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.749(2)
_cell_length_b                   9.4724(10)
_cell_length_c                   11.9937(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.200(3)
_cell_angle_gamma                90
_cell_volume                     2312.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5027
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      26.10

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6010
_exptl_absorpt_process_details   SADABS
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II Quasar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23818
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.001
_diffrn_reflns_theta_max         26.095
_diffrn_reflns_theta_full        25.242
_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             2297
_reflns_number_gt                1504
_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       'Bruker APEX2'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
All non-hydrogens were refined anisotropically. Hydrogen atoms were assigned to ideal positions and refined isotropically using a riding model.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0577P)²+2.7930P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2297
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1042
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
Na1 Na 0.500000 0.05755(13) 0.250000 0.0220(3) Uani 1 2 d S T P . .
Na2 Na 0.000000 0.500000 0.500000 0.0227(3) Uani 1 2 d S . P . .
O1 O 0.55674(7) 0.19402(17) 0.41741(13) 0.0259(4) Uani 1 1 d . . . . .
N1 N 0.41004(9) 0.0824(2) 0.35179(15) 0.0235(5) Uani 1 1 d . . . . .
N2 N 0.05259(9) 0.3671(2) 0.37569(16) 0.0233(5) Uani 1 1 d . . . . .
C5 C 0.16741(10) 0.2723(2) 0.36910(17) 0.0193(5) Uani 1 1 d . . . . .
C1 C 0.35754(11) 0.1216(2) 0.35695(18) 0.0200(5) Uani 1 1 d . . . . .
C2 C 0.29430(10) 0.1708(2) 0.36204(17) 0.0188(5) Uani 1 1 d . . . . .
C3 C 0.24320(10) 0.0763(2) 0.37752(17) 0.0202(5) Uani 1 1 d . . . . .
H3 H 0.251893 -0.021995 0.385638 0.024 Uiso 1 1 calc R U . . .
C7 C 0.27909(11) 0.3170(2) 0.34521(18) 0.0195(5) Uani 1 1 d . . . . .
H7 H 0.311951 0.380798 0.331282 0.023 Uiso 1 1 calc R U . . .
C6 C 0.21790(10) 0.3658(2) 0.34892(17) 0.0200(5) Uani 1 1 d . . . . .
H6 H 0.208616 0.463558 0.337930 0.024 Uiso 1 1 calc R U . . .
C8 C 0.10467(11) 0.3235(2) 0.37287(17) 0.0202(5) Uani 1 1 d . . . . .
C4 C 0.18241(11) 0.1260(2) 0.38071(18) 0.0206(5) Uani 1 1 d . . . . .
H4 H 0.148975 0.061469 0.390944 0.025 Uiso 1 1 calc R U . . .
C12 C 0.62771(11) 0.2003(3) 0.4457(2) 0.0290(6) Uani 1 1 d . . . . .
H12A H 0.645392 0.243713 0.382780 0.035 Uiso 1 1 calc R U . . .
H12B H 0.646400 0.104254 0.459607 0.035 Uiso 1 1 calc R U . . .
C9 C 0.53527(13) 0.3287(3) 0.4506(2) 0.0333(6) Uani 1 1 d . . . . .
H9A H 0.489089 0.323903 0.460715 0.040 Uiso 1 1 calc R U . . .
H9B H 0.538768 0.401235 0.392651 0.040 Uiso 1 1 calc R U . . .
C11 C 0.64485(12) 0.2895(3) 0.5523(2) 0.0319(6) Uani 1 1 d . . . . .
H11A H 0.679201 0.359654 0.545159 0.038 Uiso 1 1 calc R U . . .
H11B H 0.660724 0.229708 0.619723 0.038 Uiso 1 1 calc R U . . .
C10 C 0.58065(13) 0.3626(3) 0.5618(2) 0.0414(7) Uani 1 1 d . . . . .
H10A H 0.563030 0.325156 0.626857 0.050 Uiso 1 1 calc R U . . .
H10B H 0.587010 0.465814 0.571202 0.050 Uiso 1 1 calc R U . . .


_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
Na1 N1 2.4322(18) . ?
Na1 N1 2.4323(18) 2_655 ?
Na1 N2 2.466(2) 4_545 ?
Na1 N2 2.466(2) 3_545 ?
Na1 O1 2.4839(17) 2_655 ?
Na1 O1 2.4839(17) . ?
Na1 Na2 3.0476(4) 4_545 ?
Na1 Na2 3.0476(4) 3_545 ?
Na2 N2 2.3730(18) . ?
Na2 N2 2.3730(18) 5_566 ?
Na2 N1 2.4424(18) 7_556 ?
Na2 N1 2.4424(18) 3_455 ?
Na2 O1 2.4895(16) 3_455 ?
Na2 O1 2.4895(16) 7_556 ?
O1 C9 1.433(3) . ?
O1 C12 1.447(3) . ?
N1 C1 1.164(3) . ?
N2 C8 1.163(3) . ?
C5 C8 1.398(3) . ?
C5 C4 1.422(3) . ?
C5 C6 1.428(3) . ?
C1 C2 1.405(3) . ?
C2 C7 1.426(3) . ?
C2 C3 1.427(3) . ?
C3 C4 1.354(3) . ?
C3 H3 0.9500 . ?
C7 C6 1.360(3) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
C4 H4 0.9500 . ?
C12 C11 1.517(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C9 C10 1.510(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 C10 1.525(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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
N1 Na1 N1 168.88(11) . 2_655 ?
N1 Na1 N2 94.94(6) . 4_545 ?
N1 Na1 N2 93.19(6) 2_655 4_545 ?
N1 Na1 N2 93.19(6) . 3_545 ?
N1 Na1 N2 94.94(6) 2_655 3_545 ?
N2 Na1 N2 85.93(10) 4_545 3_545 ?
N1 Na1 O1 93.78(6) . 2_655 ?
N1 Na1 O1 80.40(6) 2_655 2_655 ?
N2 Na1 O1 78.62(6) 4_545 2_655 ?
N2 Na1 O1 163.53(7) 3_545 2_655 ?
N1 Na1 O1 80.40(6) . . ?
N1 Na1 O1 93.78(6) 2_655 . ?
N2 Na1 O1 163.53(7) 4_545 . ?
N2 Na1 O1 78.62(6) 3_545 . ?
O1 Na1 O1 117.28(9) 2_655 . ?
N1 Na1 Na2 131.14(4) . 4_545 ?
N1 Na1 Na2 51.45(4) 2_655 4_545 ?
N2 Na1 Na2 49.62(4) 4_545 4_545 ?
N2 Na1 Na2 112.71(6) 3_545 4_545 ?
O1 Na1 Na2 52.29(4) 2_655 4_545 ?
O1 Na1 Na2 142.92(4) . 4_545 ?
N1 Na1 Na2 51.45(4) . 3_545 ?
N1 Na1 Na2 131.13(4) 2_655 3_545 ?
N2 Na1 Na2 112.71(6) 4_545 3_545 ?
N2 Na1 Na2 49.62(4) 3_545 3_545 ?
O1 Na1 Na2 142.92(4) 2_655 3_545 ?
O1 Na1 Na2 52.29(4) . 3_545 ?
Na2 Na1 Na2 159.39(5) 4_545 3_545 ?
N2 Na2 N2 180.00(8) . 5_566 ?
N2 Na2 N1 84.72(6) . 7_556 ?
N2 Na2 N1 95.29(6) 5_566 7_556 ?
N2 Na2 N1 95.28(6) . 3_455 ?
N2 Na2 N1 84.71(6) 5_566 3_455 ?
N1 Na2 N1 180.0 7_556 3_455 ?
N2 Na2 O1 80.28(6) . 3_455 ?
N2 Na2 O1 99.72(6) 5_566 3_455 ?
N1 Na2 O1 99.90(6) 7_556 3_455 ?
N1 Na2 O1 80.10(6) 3_455 3_455 ?
N2 Na2 O1 99.72(6) . 7_556 ?
N2 Na2 O1 80.28(6) 5_566 7_556 ?
N1 Na2 O1 80.10(6) 7_556 7_556 ?
N1 Na2 O1 99.90(6) 3_455 7_556 ?
O1 Na2 O1 180.00(5) 3_455 7_556 ?
N2 Na2 Na1 52.33(5) . 3_455 ?
N2 Na2 Na1 127.67(5) 5_566 3_455 ?
N1 Na2 Na1 128.84(4) 7_556 3_455 ?
N1 Na2 Na1 51.16(4) 3_455 3_455 ?
O1 Na2 Na1 52.13(4) 3_455 3_455 ?
O1 Na2 Na1 127.87(4) 7_556 3_455 ?
N2 Na2 Na1 127.67(5) . 7_556 ?
N2 Na2 Na1 52.33(5) 5_566 7_556 ?
N1 Na2 Na1 51.16(4) 7_556 7_556 ?
N1 Na2 Na1 128.84(4) 3_455 7_556 ?
O1 Na2 Na1 127.87(4) 3_455 7_556 ?
O1 Na2 Na1 52.13(4) 7_556 7_556 ?
Na1 Na2 Na1 180.0 3_455 7_556 ?
C9 O1 C12 104.82(18) . . ?
C9 O1 Na1 124.32(14) . . ?
C12 O1 Na1 120.77(13) . . ?
C9 O1 Na2 110.50(14) . 3_545 ?
C12 O1 Na2 118.39(14) . 3_545 ?
Na1 O1 Na2 75.58(5) . 3_545 ?
C1 N1 Na1 151.06(17) . . ?
C1 N1 Na2 130.86(16) . 3_545 ?
Na1 N1 Na2 77.39(5) . 3_545 ?
C8 N2 Na2 138.56(17) . . ?
C8 N2 Na1 123.03(16) . 3_455 ?
Na2 N2 Na1 78.05(6) . 3_455 ?
C8 C5 C4 121.5(2) . . ?
C8 C5 C6 120.6(2) . . ?
C4 C5 C6 117.9(2) . . ?
N1 C1 C2 179.1(3) . . ?
C1 C2 C7 119.9(2) . . ?
C1 C2 C3 121.4(2) . . ?
C7 C2 C3 118.54(19) . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C6 C7 C2 120.5(2) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
N2 C8 C5 179.5(3) . . ?
C3 C4 C5 121.6(2) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
O1 C12 C11 106.35(19) . . ?
O1 C12 H12A 110.5 . . ?
C11 C12 H12A 110.5 . . ?
O1 C12 H12B 110.5 . . ?
C11 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
O1 C9 C10 105.1(2) . . ?
O1 C9 H9A 110.7 . . ?
C10 C9 H9A 110.7 . . ?
O1 C9 H9B 110.7 . . ?
C10 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
C12 C11 C10 104.5(2) . . ?
C12 C11 H11A 110.8 . . ?
C10 C11 H11A 110.8 . . ?
C12 C11 H11B 110.8 . . ?
C10 C11 H11B 110.8 . . ?
H11A C11 H11B 108.9 . . ?
C9 C10 C11 104.0(2) . . ?
C9 C10 H10A 111.0 . . ?
C11 C10 H10A 111.0 . . ?
C9 C10 H10B 111.0 . . ?
C11 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.058



