# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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. 
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data_22019499339_0m_tw
_database_code_depnum_ccdc_archive 'CCDC 2208014'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-09-19 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-10-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H7 N5 Na2 O4'
_chemical_formula_sum            'C4 H7 N5 Na2 O4'
_chemical_formula_weight         235.13
_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'
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'

_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                   6.8450(7)
_cell_length_b                   7.2316(7)
_cell_length_c                   10.2686(10)
_cell_angle_alpha                71.886(4)
_cell_angle_beta                 71.147(4)
_cell_angle_gamma                82.079(4)
_cell_volume                     456.80(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3422
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      27.515
_cell_measurement_theta_min      2.966
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.8491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0690 before and 0.0456 after correction.
The Ratio of minimum to maximum transmission is 0.9149.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2047
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.515
_diffrn_reflns_theta_min         2.966
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_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                1818
_reflns_number_total             2047
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2047
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.090
_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)+(0.0242P)²+0.6514P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1036
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.841(3)
 0.159(3)
2. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C4(H4A,H4B,H4C)
3.b Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_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
Na2 Na 1.03809(13) 0.80008(12) 0.84582(9) 0.0136(2) Uani 1 1 d . . . . .
Na1 Na 0.87369(13) 0.78441(12) 0.55587(9) 0.0141(2) Uani 1 1 d . . . . .
O2 O 0.1927(2) 0.8741(2) 0.57720(16) 0.0149(3) Uani 1 1 d . . . . .
O3 O 0.7198(2) 0.8052(2) 0.80269(16) 0.0175(3) Uani 1 1 d . . . . .
O1 O 0.5075(2) 0.7556(2) 0.59000(16) 0.0173(3) Uani 1 1 d . . . . .
O4 O 0.3885(2) 0.7630(3) 0.83878(17) 0.0204(4) Uani 1 1 d . . . . .
H4 H 0.433535 0.757480 0.753611 0.031 Uiso 1 1 calc R U . . .
N2 N 0.9590(3) 0.8367(3) 0.19393(19) 0.0154(4) Uani 1 1 d . . . . .
N3 N 0.9538(3) 0.7272(3) 0.11261(19) 0.0155(4) Uani 1 1 d . . . . .
N1 N 0.9759(3) 0.7184(3) 0.31793(19) 0.0152(4) Uani 1 1 d . . . . .
N4 N 0.9667(3) 0.5424(3) 0.18661(19) 0.0167(4) Uani 1 1 d . . . . .
N5 N 0.9824(3) 0.5373(3) 0.3133(2) 0.0173(4) Uani 1 1 d . . . . .
C1 C 0.3666(3) 0.8029(3) 0.5258(2) 0.0135(4) Uani 1 1 d . . . . .
C3 C 0.5418(3) 0.7757(3) 0.8832(2) 0.0156(4) Uani 1 1 d . . . . .
C2 C 0.4247(4) 0.7627(3) 0.3829(2) 0.0188(5) Uani 1 1 d . . . . .
H2A H 0.435008 0.621688 0.397075 0.028 Uiso 1 1 calc R U . . .
H2B H 0.558266 0.818614 0.323217 0.028 Uiso 1 1 calc R U . . .
H2C H 0.318938 0.821468 0.335222 0.028 Uiso 1 1 calc R U . . .
C4 C 0.4870(4) 0.7491(4) 1.0416(2) 0.0243(5) Uani 1 1 d . . . . .
H4A H 0.607323 0.774423 1.064569 0.036 Uiso 1 1 calc R U . . .
H4B H 0.445420 0.615311 1.094138 0.036 Uiso 1 1 calc R U . . .
H4C H 0.372622 0.840265 1.069613 0.036 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
Na2 Na1 3.5432(12) . ?
Na2 Na1 4.1941(12) 2_776 ?
Na2 O2 2.5232(17) 1_655 ?
Na2 O3 2.3526(18) . ?
Na2 O4 2.3565(18) 1_655 ?
Na2 N2 2.532(2) 2_776 ?
Na2 N3 2.506(2) 1_556 ?
Na2 N4 2.605(2) 2_766 ?
Na1 Na1 3.4653(17) 2_776 ?
Na1 O2 2.4546(18) 1_655 ?
Na1 O2 2.4829(17) 2_676 ?
Na1 O3 2.4544(18) . ?
Na1 O1 2.4454(18) . ?
Na1 N1 2.493(2) . ?
Na1 N5 2.543(2) 2_766 ?
O2 C1 1.247(3) . ?
O3 C3 1.235(3) . ?
O1 C1 1.289(3) . ?
O4 H4 0.8400 . ?
O4 C3 1.296(3) . ?
N2 N3 1.328(3) . ?
N2 N1 1.325(3) . ?
N3 N4 1.323(3) . ?
N1 N5 1.320(3) . ?
N4 N5 1.328(3) . ?
C1 C2 1.500(3) . ?
C3 C4 1.502(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 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
Na1 Na2 Na1 52.39(3) . 2_776 ?
O2 Na2 Na1 32.79(4) 1_655 2_776 ?
O2 Na2 Na1 43.85(4) 1_655 . ?
O2 Na2 N2 85.87(6) 1_655 2_776 ?
O2 Na2 N4 79.68(6) 1_655 2_766 ?
O3 Na2 Na1 77.83(5) . 2_776 ?
O3 Na2 Na1 43.64(4) . . ?
O3 Na2 O2 85.51(6) . 1_655 ?
O3 Na2 O4 165.49(7) . 1_655 ?
O3 Na2 N2 96.12(6) . 2_776 ?
O3 Na2 N3 105.37(7) . 1_556 ?
O3 Na2 N4 76.35(6) . 2_766 ?
O4 Na2 Na1 95.94(5) 1_655 2_776 ?
O4 Na2 Na1 122.45(5) 1_655 . ?
O4 Na2 O2 82.39(6) 1_655 1_655 ?
O4 Na2 N2 90.98(7) 1_655 2_776 ?
O4 Na2 N3 86.82(6) 1_655 1_556 ?
O4 Na2 N4 93.56(7) 1_655 2_766 ?
N2 Na2 Na1 101.58(5) 2_776 . ?
N2 Na2 Na1 55.86(4) 2_776 2_776 ?
N2 Na2 N4 164.13(7) 2_776 2_766 ?
N3 Na2 Na1 146.53(6) 1_556 . ?
N3 Na2 Na1 148.64(5) 1_556 2_776 ?
N3 Na2 O2 169.12(7) 1_556 1_655 ?
N3 Na2 N2 92.95(6) 1_556 2_776 ?
N3 Na2 N4 102.48(7) 1_556 2_766 ?
N4 Na2 Na1 63.29(5) 2_766 . ?
N4 Na2 Na1 108.48(5) 2_766 2_776 ?
Na2 Na1 Na2 127.61(3) . 2_776 ?
Na1 Na1 Na2 54.10(3) 2_776 2_776 ?
Na1 Na1 Na2 73.51(3) 2_776 . ?
O2 Na1 Na2 107.33(5) 2_676 . ?
O2 Na1 Na2 45.40(4) 1_655 . ?
O2 Na1 Na2 33.39(4) 2_676 2_776 ?
O2 Na1 Na2 90.96(4) 1_655 2_776 ?
O2 Na1 Na1 45.10(4) 2_676 2_776 ?
O2 Na1 Na1 45.76(4) 1_655 2_776 ?
O2 Na1 O2 90.85(6) 1_655 2_676 ?
O2 Na1 N1 85.48(6) 2_676 . ?
O2 Na1 N1 105.15(6) 1_655 . ?
O2 Na1 N5 76.52(6) 1_655 2_766 ?
O2 Na1 N5 167.28(7) 2_676 2_766 ?
O3 Na1 Na2 132.76(5) . 2_776 ?
O3 Na1 Na2 41.42(4) . . ?
O3 Na1 Na1 93.15(5) . 2_776 ?
O3 Na1 O2 99.51(6) . 2_676 ?
O3 Na1 O2 84.87(6) . 1_655 ?
O3 Na1 N1 168.84(7) . . ?
O3 Na1 N5 81.20(6) . 2_766 ?
O1 Na1 Na2 120.03(5) . . ?
O1 Na1 Na2 93.56(4) . 2_776 ?
O1 Na1 Na1 125.93(6) . 2_776 ?
O1 Na1 O2 161.49(6) . 1_655 ?
O1 Na1 O2 83.20(6) . 2_676 ?
O1 Na1 O3 78.90(6) . . ?
O1 Na1 N1 91.89(6) . . ?
O1 Na1 N5 109.31(7) . 2_766 ?
N1 Na1 Na2 146.29(6) . . ?
N1 Na1 Na2 53.38(5) . 2_776 ?
N1 Na1 Na1 97.39(6) . 2_776 ?
N1 Na1 N5 96.15(7) . 2_766 ?
N5 Na1 Na2 64.85(5) 2_766 . ?
N5 Na1 Na2 143.14(5) 2_766 2_776 ?
N5 Na1 Na1 122.26(6) 2_766 2_776 ?
Na1 O2 Na2 113.82(6) 2_676 1_455 ?
Na1 O2 Na2 90.75(6) 1_455 1_455 ?
Na1 O2 Na1 89.15(6) 1_455 2_676 ?
C1 O2 Na2 119.84(13) . 1_455 ?
C1 O2 Na1 123.08(14) . 1_455 ?
C1 O2 Na1 114.60(13) . 2_676 ?
Na2 O3 Na1 94.94(6) . . ?
C3 O3 Na2 132.68(14) . . ?
C3 O3 Na1 129.90(14) . . ?
C1 O1 Na1 143.36(14) . . ?
Na2 O4 H4 95.1 1_455 . ?
C3 O4 Na2 153.78(14) . 1_455 ?
C3 O4 H4 109.5 . . ?
N3 N2 Na2 134.03(14) . 2_776 ?
N1 N2 Na2 118.16(14) . 2_776 ?
N1 N2 N3 107.72(17) . . ?
N2 N3 Na2 131.33(14) . 1_554 ?
N4 N3 Na2 117.06(13) . 1_554 ?
N4 N3 N2 108.07(17) . . ?
N2 N1 Na1 128.45(14) . . ?
N5 N1 Na1 119.09(13) . . ?
N5 N1 N2 108.31(17) . . ?
N3 N4 Na2 138.11(14) . 2_766 ?
N3 N4 N5 107.94(17) . . ?
N5 N4 Na2 113.94(13) . 2_766 ?
N1 N5 Na1 133.89(14) . 2_766 ?
N1 N5 N4 107.95(17) . . ?
N4 N5 Na1 114.57(14) . 2_766 ?
O2 C1 O1 123.64(19) . . ?
O2 C1 C2 121.33(19) . . ?
O1 C1 C2 115.03(19) . . ?
O3 C3 O4 123.1(2) . . ?
O3 C3 C4 122.2(2) . . ?
O4 C3 C4 114.7(2) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

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
Na2 O2 C1 O1 -27.3(3) 1_455 . . . ?
Na2 O2 C1 C2 151.63(16) 1_455 . . . ?
Na2 O3 C3 O4 -171.51(15) . . . . ?
Na2 O3 C3 C4 7.7(3) . . . . ?
Na2 O4 C3 O3 -148.8(3) 1_455 . . . ?
Na2 O4 C3 C4 32.0(4) 1_455 . . . ?
Na2 N2 N3 Na2 19.0(3) 2_776 . . 1_554 ?
Na2 N2 N3 N4 176.55(15) 2_776 . . . ?
Na2 N2 N1 Na1 26.9(2) 2_776 . . . ?
Na2 N2 N1 N5 -176.62(13) 2_776 . . . ?
Na2 N3 N4 Na2 -21.1(3) 1_554 . . 2_766 ?
Na2 N3 N4 N5 160.47(14) 1_554 . . . ?
Na2 N4 N5 Na1 20.44(18) 2_766 . . 2_766 ?
Na2 N4 N5 N1 -177.86(13) 2_766 . . . ?
Na1 O2 C1 O1 -140.31(17) 1_455 . . . ?
Na1 O2 C1 O1 113.51(19) 2_676 . . . ?
Na1 O2 C1 C2 -67.6(2) 2_676 . . . ?
Na1 O2 C1 C2 38.6(3) 1_455 . . . ?
Na1 O3 C3 O4 -14.0(3) . . . . ?
Na1 O3 C3 C4 165.19(16) . . . . ?
Na1 O1 C1 O2 -132.4(2) . . . . ?
Na1 O1 C1 C2 48.7(3) . . . . ?
Na1 N1 N5 Na1 -45.2(2) . . . 2_766 ?
Na1 N1 N5 N4 158.18(14) . . . . ?
N2 N3 N4 Na2 177.67(16) . . . 2_766 ?
N2 N3 N4 N5 -0.7(2) . . . . ?
N2 N1 N5 Na1 155.81(16) . . . 2_766 ?
N2 N1 N5 N4 -0.8(2) . . . . ?
N3 N2 N1 Na1 -156.07(14) . . . . ?
N3 N2 N1 N5 0.4(2) . . . . ?
N3 N4 N5 Na1 -160.73(14) . . . 2_766 ?
N3 N4 N5 N1 1.0(2) . . . . ?
N1 N2 N3 Na2 -157.32(15) . . . 1_554 ?
N1 N2 N3 N4 0.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.841(3)
2 0.159(3)

