# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 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. 
# 
#######################################################################

data_lr88-b0
_database_code_depnum_ccdc_archive 'CCDC 2164892'
loop_
_audit_author_name
_audit_author_address
'hassan allouchi'
;University of Tours
France
;
_audit_update_record             
;
2023-01-23 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H11 N7 O8'
_chemical_formula_weight         261.18

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.4245(4)
_cell_length_b                   8.4297(6)
_cell_length_c                   10.5226(7)
_cell_angle_alpha                74.821(6)
_cell_angle_beta                 84.243(6)
_cell_angle_gamma                76.240(6)
_cell_volume                     533.76(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2664
_cell_measurement_theta_min      2.8381
_cell_measurement_theta_max      31.4490

_exptl_crystal_description       colourless
_exptl_crystal_colour            block
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_F_000             272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.703
_exptl_crystal_size_mid          0.406
_exptl_crystal_size_min          0.273
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2 2 3 0.0700 -1.9845 2.0099
3.0089 -0.0140 0.3531 0.0767 1 0
0 0.1800 0.9965 -0.0056 -0.0023 -0.0703
-0.0864 -0.0230 1 1 0 0.0800
0.9987 0.9950 0.0013 -0.0970 -0.0602 0.0580
4 11 7 0.1250 4.0194 10.9780
7.0237 -0.8112 0.2412 0.4928 -1 -8
-13 0.1250 -1.0316 -7.9883 -13.0133 0.7219
-0.6778 -0.0559 -4 0 -3 0.2150
-3.9900 0.0248 -2.9874 0.3819 0.2175 0.2234
7 -4 3 0.2450 6.9706 -4.0437
2.9656 -0.4855 -0.5815 -0.6165 3 2
3 0.2100 2.9978 1.9819 2.9971 -0.3653
-0.0788 -0.0383 2 1 0 0.1000
1.9951 0.9894 -0.0010 -0.1673 -0.1466 0.0351
0 -1 -2 0.1000 -0.0049 -0.9989
-2.0016 0.0941 -0.1115 0.0066 -1 0
0 0.1800 -0.9965 0.0056 0.0023 0.0703
0.0864 0.0230 0 -1 0 0.2400
-0.0022 -1.0006 -0.0037 0.0268 -0.0262 -0.0810
0 1 2 0.2000 0.0049 0.9989
2.0016 -0.0941 0.1115 -0.0066 3 -1
5 0.3100 2.9940 -1.0214 4.9839 -0.3522
-0.0720 -0.3690 -2 -1 0 0.2300
-1.9951 -0.9894 0.0010 0.1673 0.1466 -0.0351



_exptl_absorpt_coefficient_mu    0.160
_shelx_estimated_absorpt_T_min   0.896
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET)
(compiled Aug 27 2009,17:19:36)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_detector_area_resol_mean 8.3622
_diffrn_reflns_number            4744
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.843
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_full        25.242

_diffrn_orient_matrix_UB_11      -0.0707287793
_diffrn_orient_matrix_UB_12      -0.0264972514
_diffrn_orient_matrix_UB_13      -0.0336034145
_diffrn_orient_matrix_UB_21      -0.0864414368
_diffrn_orient_matrix_UB_22      0.0262095419
_diffrn_orient_matrix_UB_23      0.0428473625
_diffrn_orient_matrix_UB_31      -0.0227201831
_diffrn_orient_matrix_UB_32      0.0812019220
_diffrn_orient_matrix_UB_33      -0.0437484217
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -54.00   60.75   0.7500   45.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -79.0000    0.0000 153

#__ type_ start__ end____ width___ exp.time_
  2 omega  -54.00   60.75   0.7500   45.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -79.0000   90.0000 153

#__ type_ start__ end____ width___ exp.time_
  3 omega  -54.00   60.75   0.7500   45.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -79.0000  180.0000 153

#__ type_ start__ end____ width___ exp.time_
  4 omega  -54.00   60.75   0.7500   45.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -79.0000  270.0000 153

;
_diffrn_measurement_method       'ω scans'

_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2622
_reflns_number_gt                1959
_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       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2013)'
_computing_publication_material  
'WinGX (Farrugia, 2012), publCIF (Westrip, 2013), SHELXL (Sheldrick, 2014)'
_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)+(0.0803P)²+0.0225P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2622
_refine_ls_number_parameters     178
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1328
_refine_ls_wR_factor_gt          0.1256
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
C2 C 0.2510(2) 0.19343(18) 0.23057(14) 0.0345(3) Uani 1 1 d . . . . .
C4 C 0.3372(2) -0.06424(18) 0.27630(14) 0.0345(3) Uani 1 1 d . . . . .
O1 O 0.1491(3) 0.47453(16) 0.22055(14) 0.0751(5) Uani 1 1 d . . . . .
O2 O 0.2411(3) 0.39867(16) 0.03932(13) 0.0660(4) Uani 1 1 d . . . . .
N1 N 0.2102(2) 0.36806(16) 0.15782(13) 0.0444(3) Uani 1 1 d . . . . .
N3 N 0.32132(19) 0.06528(15) 0.17209(11) 0.0339(3) Uani 1 1 d . . . . .
N5 N 0.2800(2) -0.01345(16) 0.38778(13) 0.0437(3) Uani 1 1 d . . . . .
H5 H 0.2799 -0.0788 0.4657 0.052 Uiso 1 1 calc R U . . .
N6 N 0.2223(2) 0.15678(16) 0.35854(13) 0.0427(3) Uani 1 1 d . . . . .
N7 N 0.3925(2) -0.23110(17) 0.27483(14) 0.0430(3) Uani 1 1 d . . . . .
N8 N 0.5065(2) -0.26207(16) 0.15711(13) 0.0396(3) Uani 1 1 d . . . . .
H8A H 0.5628 -0.3718 0.1690 0.059 Uiso 1 1 calc R U . . .
H8B H 0.6109 -0.2056 0.1376 0.059 Uiso 1 1 calc R U . . .
H8C H 0.4169 -0.2281 0.0912 0.059 Uiso 1 1 calc R U . . .
H7 H 0.443(3) -0.294(3) 0.338(2) 0.047 Uiso 1 1 d . U . . .
N9 N 0.6747(2) 0.31131(17) 0.32451(13) 0.0415(3) Uani 1 1 d . . . . .
O3 O 0.6219(2) 0.38476(18) 0.41427(13) 0.0635(4) Uani 1 1 d . . . . .
O4 O 0.7318(2) 0.15552(15) 0.34816(12) 0.0568(4) Uani 1 1 d . . . . .
O5 O 0.6673(3) 0.39355(15) 0.20718(12) 0.0640(4) Uani 1 1 d . . . . .
O1W O -0.20437(18) 0.18617(16) 0.02900(12) 0.0440(3) Uani 1 1 d . . . . .
H1A H -0.233(3) 0.261(3) 0.075(2) 0.066 Uiso 1 1 d . U . . .
H1B H -0.194(3) 0.092(3) 0.082(2) 0.066 Uiso 1 1 d . U . . .
O2W O -0.12720(19) -0.15084(16) 0.16331(14) 0.0476(3) Uani 1 1 d . . . . .
H2A H -0.101(3) -0.201(3) 0.243(3) 0.071 Uiso 1 1 d . U . . .
H2B H -0.020(4) -0.185(3) 0.112(3) 0.071 Uiso 1 1 d . U . . .
O3W O 0.1389(4) 0.3272(3) 0.57328(17) 0.1013(7) Uani 1 1 d D . . . .
H3A H 0.139(5) 0.287(4) 0.506(3) 0.124(12) Uiso 1 1 d D . . . .
H3B H 0.117(6) 0.433(2) 0.545(4) 0.176(19) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 N6 1.3046(19) . ?
C2 N3 1.3454(18) . ?
C2 N1 1.445(2) . ?
C4 N3 1.3219(19) . ?
C4 N5 1.3402(19) . ?
C4 N7 1.3702(19) . ?
O1 N1 1.2190(18) . ?
O2 N1 1.2111(18) . ?
N5 N6 1.3527(18) . ?
N5 H5 0.8600 . ?
N7 N8 1.4267(18) . ?
N7 H7 0.78(2) . ?
N8 H8A 0.8900 . ?
N8 H8B 0.8900 . ?
N8 H8C 0.8900 . ?
N9 O3 1.2379(17) . ?
N9 O4 1.2406(18) . ?
N9 O5 1.2470(18) . ?
O1W H1A 0.87(3) . ?
O1W H1B 0.83(3) . ?
O2W H2A 0.85(2) . ?
O2W H2B 0.88(3) . ?
O3W H3A 0.866(17) . ?
O3W H3B 0.848(18) . ?

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
N6 C2 N3 117.95(13) . . ?
N6 C2 N1 119.31(13) . . ?
N3 C2 N1 122.73(13) . . ?
N3 C4 N5 111.40(12) . . ?
N3 C4 N7 126.13(13) . . ?
N5 C4 N7 122.37(14) . . ?
O2 N1 O1 124.54(14) . . ?
O2 N1 C2 117.98(13) . . ?
O1 N1 C2 117.47(14) . . ?
C4 N3 C2 100.24(11) . . ?
C4 N5 N6 109.34(12) . . ?
C4 N5 H5 125.3 . . ?
N6 N5 H5 125.3 . . ?
C2 N6 N5 101.06(12) . . ?
C4 N7 N8 113.88(13) . . ?
C4 N7 H7 116.7(15) . . ?
N8 N7 H7 112.4(14) . . ?
N7 N8 H8A 109.5 . . ?
N7 N8 H8B 109.5 . . ?
H8A N8 H8B 109.5 . . ?
N7 N8 H8C 109.5 . . ?
H8A N8 H8C 109.5 . . ?
H8B N8 H8C 109.5 . . ?
O3 N9 O4 121.42(14) . . ?
O3 N9 O5 120.13(14) . . ?
O4 N9 O5 118.43(13) . . ?
H1A O1W H1B 107(2) . . ?
H2A O2W H2B 110(2) . . ?
H3A O3W H3B 107(2) . . ?

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
N6 C2 N1 O2 178.94(15) . . . . ?
N3 C2 N1 O2 0.1(2) . . . . ?
N6 C2 N1 O1 -0.3(2) . . . . ?
N3 C2 N1 O1 -179.18(15) . . . . ?
N5 C4 N3 C2 -0.16(16) . . . . ?
N7 C4 N3 C2 176.35(15) . . . . ?
N6 C2 N3 C4 0.06(17) . . . . ?
N1 C2 N3 C4 178.93(14) . . . . ?
N3 C4 N5 N6 0.22(18) . . . . ?
N7 C4 N5 N6 -176.44(14) . . . . ?
N3 C2 N6 N5 0.07(18) . . . . ?
N1 C2 N6 N5 -178.84(13) . . . . ?
C4 N5 N6 C2 -0.17(16) . . . . ?
N3 C4 N7 N8 21.2(2) . . . . ?
N5 C4 N7 N8 -162.63(13) . . . . ?

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
N5 H5 O3 0.86 2.51 3.232(2) 141.4 2_656
N5 H5 O4 0.86 1.89 2.7238(18) 161.4 2_656
N5 H5 N9 0.86 2.53 3.3768(18) 169.4 2_656
N7 H7 O3 0.78(2) 2.54(2) 3.189(2) 141.9(17) 2_656
N8 H8A O5 0.89 1.88 2.7666(17) 175.2 1_545
N8 H8B O2W 0.89 1.91 2.7448(18) 155.8 1_655
N8 H8C O1W 0.89 1.86 2.7436(17) 169.8 2
O1W H1A O5 0.87(3) 1.97(3) 2.8235(17) 167(2) 1_455
O1W H1B O2W 0.83(3) 1.96(3) 2.7716(19) 164(2) .
O2W H2A O3W 0.85(2) 1.97(3) 2.784(2) 160(2) 2_556
O2W H2B O1W 0.88(3) 1.96(3) 2.8053(18) 162(2) 2
O3W H3A N6 0.866(17) 2.080(19) 2.924(2) 165(3) .
O3W H3B O3W 0.848(18) 2.42(3) 3.127(4) 142(3) 2_566

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.081



