# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2209418'
loop_
_audit_author_name
_audit_author_address
'Barzin Safarkoopayeh '
;College of Science, School of Chemistry, Tehran University, Tehran, Iran
Iran
;
_audit_update_record             
;
2022-12-07 deposited with the CCDC.	2022-12-19 downloaded from the CCDC.
;
_audit_creation_date             2022-11-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H32 N4 O8'
_chemical_formula_sum            'C18 H32 N4 O8'
_chemical_formula_weight         432.47
_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'
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                   7.7598(16)
_cell_length_b                   15.946(3)
_cell_length_c                   8.3038(17)
_cell_angle_alpha                90
_cell_angle_beta                 97.56(3)
_cell_angle_gamma                90
_cell_volume                     1018.6(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6151
_cell_measurement_temperature    290
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.8
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5209
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         2.555
_diffrn_ambient_temperature      290
_diffrn_detector                 'image-plate detector'
_diffrn_detector_area_resol_mean 0.81
_diffrn_detector_type            MAR345-dtb
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device       'one-circle diffractometer'
_diffrn_measurement_device_type  MAR345
_diffrn_measurement_method       'image-plate detector - phi oscillation'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_target            Mo
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1256
_reflns_number_total             1724
_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       'Automar software package (3.3a, 2015)'
_computing_data_collection       'MAR345 dtb Program (1.24-4, 2013)'
_computing_data_reduction        'Automar software package (3.3a, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       0.060(15)
_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   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1724
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1197
_refine_ls_R_factor_gt           0.0912
_refine_ls_restrained_S_all      1.108
_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)+(0.1476P)²+1.5583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2369
_refine_ls_wR_factor_ref         0.2628
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
2. Restrained distances
 O5_$1-O1
 2.7 with sigma of 0.01
3. Rigid bond restraints
 O5, C12
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4.a Ternary CH refined with riding coordinates:
 N2(H2)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C13(H13A,H13B), C1(H1A,H1B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 -0.0030(4) 0.57836(18) 0.3609(4) 0.0457(9) Uani 1 1 d D . . . .
N2 N 0.2604(4) 0.4875(2) 0.2862(4) 0.0377(9) Uani 1 1 d . . . . .
H2 H 0.271850 0.525905 0.379215 0.045 Uiso 1 1 calc R U . . .
N1 N 0.5980(4) 0.3658(2) 0.5464(4) 0.0384(9) Uani 1 1 d . . . . .
O4 O -0.2067(4) 0.4892(2) 0.2503(4) 0.0526(10) Uani 1 1 d . . . . .
O5 O 0.6476(6) 0.2172(2) 0.2363(5) 0.0743(13) Uani 1 1 d . U . . .
C6 C -0.0554(5) 0.5103(3) 0.2955(5) 0.0385(10) Uani 1 1 d . . . . .
C7 C 0.5858(6) 0.3948(3) 0.8410(6) 0.0484(12) Uani 1 1 d . . . . .
H7A H 0.581829 0.366061 0.943377 0.058 Uiso 1 1 calc R U . . .
H7B H 0.474846 0.422652 0.812187 0.058 Uiso 1 1 calc R U . . .
C8 C 0.4065(5) 0.4256(3) 0.3137(5) 0.0405(11) Uani 1 1 d . . . . .
H8A H 0.515367 0.454805 0.308723 0.049 Uiso 1 1 calc R U . . .
H8B H 0.392628 0.384616 0.226596 0.049 Uiso 1 1 calc R U . . .
C9 C 0.0865(5) 0.4464(3) 0.2768(6) 0.0408(11) Uani 1 1 d . . . . .
H9A H 0.089061 0.404547 0.361872 0.049 Uiso 1 1 calc R U . . .
H9B H 0.060412 0.418138 0.173029 0.049 Uiso 1 1 calc R U . . .
C10 C 0.6969(5) 0.3186(2) 0.4388(5) 0.0397(10) Uani 1 1 d . . . . .
H10A H 0.814280 0.311400 0.493507 0.048 Uiso 1 1 calc R U . . .
H10B H 0.704293 0.352302 0.342642 0.048 Uiso 1 1 calc R U . . .
C11 C 0.4167(5) 0.3799(3) 0.4754(6) 0.0428(11) Uani 1 1 d . . . . .
H11A H 0.357993 0.412767 0.550081 0.051 Uiso 1 1 calc R U . . .
H11B H 0.357431 0.326403 0.459362 0.051 Uiso 1 1 calc R U . . .
C12 C 0.6268(6) 0.2333(3) 0.3845(6) 0.0445(11) Uani 1 1 d . U . . .
C13 C 0.2714(5) 0.5391(3) 0.1357(5) 0.0443(11) Uani 1 1 d . . . . .
H13A H 0.160643 0.566610 0.104168 0.053 Uiso 1 1 calc R U . . .
H13B H 0.292641 0.501996 0.047780 0.053 Uiso 1 1 calc R U . . .
O2 O 0.5531(7) 0.1874(2) 0.4672(5) 0.0935(17) Uani 1 1 d . . . . .
C1 C 0.6091(6) 0.3304(3) 0.7118(5) 0.0462(11) Uani 1 1 d . . . . .
H1A H 0.721580 0.303744 0.738741 0.055 Uiso 1 1 calc R U . . .
H1B H 0.520782 0.287456 0.712822 0.055 Uiso 1 1 calc R U . . .
H5 H 0.603(7) 0.172(4) 0.208(7) 0.068(17) 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
O1 C6 1.257(5) . ?
N2 H2 0.9800 . ?
N2 C8 1.498(5) . ?
N2 C9 1.493(5) . ?
N2 C13 1.508(5) . ?
N1 C10 1.460(5) . ?
N1 C11 1.469(5) . ?
N1 C1 1.477(6) . ?
O4 C6 1.231(5) . ?
O5 C12 1.288(6) . ?
O5 H5 0.82(6) . ?
C6 C9 1.523(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C13 1.524(6) 3_666 ?
C7 C1 1.513(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C11 1.521(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C12 1.512(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O2 1.199(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

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
C8 N2 H2 107.7 . . ?
C8 N2 C13 111.1(3) . . ?
C9 N2 H2 107.7 . . ?
C9 N2 C8 112.3(3) . . ?
C9 N2 C13 110.2(3) . . ?
C13 N2 H2 107.7 . . ?
C10 N1 C11 112.7(4) . . ?
C10 N1 C1 113.7(3) . . ?
C11 N1 C1 111.6(3) . . ?
C12 O5 H5 110(4) . . ?
O1 C6 C9 115.1(3) . . ?
O4 C6 O1 127.5(4) . . ?
O4 C6 C9 117.3(4) . . ?
H7A C7 H7B 107.6 . . ?
C13 C7 H7A 108.7 3_666 . ?
C13 C7 H7B 108.7 3_666 . ?
C1 C7 H7A 108.7 . . ?
C1 C7 H7B 108.7 . . ?
C1 C7 C13 114.0(4) . 3_666 ?
N2 C8 H8A 108.8 . . ?
N2 C8 H8B 108.8 . . ?
N2 C8 C11 113.6(3) . . ?
H8A C8 H8B 107.7 . . ?
C11 C8 H8A 108.8 . . ?
C11 C8 H8B 108.8 . . ?
N2 C9 C6 111.2(3) . . ?
N2 C9 H9A 109.4 . . ?
N2 C9 H9B 109.4 . . ?
C6 C9 H9A 109.4 . . ?
C6 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
N1 C10 H10A 108.1 . . ?
N1 C10 H10B 108.1 . . ?
N1 C10 C12 116.6(3) . . ?
H10A C10 H10B 107.3 . . ?
C12 C10 H10A 108.1 . . ?
C12 C10 H10B 108.1 . . ?
N1 C11 C8 111.3(3) . . ?
N1 C11 H11A 109.4 . . ?
N1 C11 H11B 109.4 . . ?
C8 C11 H11A 109.4 . . ?
C8 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
O5 C12 C10 112.2(4) . . ?
O2 C12 O5 123.7(4) . . ?
O2 C12 C10 124.0(4) . . ?
N2 C13 C7 113.0(4) . 3_666 ?
N2 C13 H13A 109.0 . . ?
N2 C13 H13B 109.0 . . ?
C7 C13 H13A 109.0 3_666 . ?
C7 C13 H13B 109.0 3_666 . ?
H13A C13 H13B 107.8 . . ?
N1 C1 C7 113.7(4) . . ?
N1 C1 H1A 108.8 . . ?
N1 C1 H1B 108.8 . . ?
C7 C1 H1A 108.8 . . ?
C7 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?

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 C6 C9 N2 -19.9(5) . . . . ?
N2 C8 C11 N1 -143.0(4) . . . . ?
N1 C10 C12 O5 142.8(4) . . . . ?
N1 C10 C12 O2 -33.9(7) . . . . ?
O4 C6 C9 N2 162.3(4) . . . . ?
C8 N2 C9 C6 164.5(3) . . . . ?
C8 N2 C13 C7 -74.6(5) . . . 3_666 ?
C9 N2 C8 C11 -63.8(5) . . . . ?
C9 N2 C13 C7 160.2(4) . . . 3_666 ?
C10 N1 C11 C8 -57.4(4) . . . . ?
C10 N1 C1 C7 152.4(4) . . . . ?
C11 N1 C10 C12 -57.6(5) . . . . ?
C11 N1 C1 C7 -78.8(4) . . . . ?
C13 N2 C8 C11 172.2(3) . . . . ?
C13 N2 C9 C6 -71.0(4) . . . . ?
C13 C7 C1 N1 -64.7(5) 3_666 . . . ?
C1 N1 C10 C12 70.6(5) . . . . ?
C1 N1 C11 C8 173.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
