# Supplementary Information (SI) for Nanoscale.
# 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_23mdw12ay
_database_code_depnum_ccdc_archive 'CCDC 2419508'
loop_
_audit_author_name
_audit_author_address
'Anna Yusov'
;New York University
United States of America
;
_audit_update_record             
;
2025-01-24 deposited with the CCDC.	2025-04-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H24 N6 O7 S2'
_chemical_formula_iupac          ?
_chemical_formula_weight         452.51

_chemical_melting_point          ?

_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                   7.2940(3)
_cell_length_b                   7.2975(3)
_cell_length_c                   11.5957(5)
_cell_angle_alpha                100.0921(15)
_cell_angle_beta                 95.3125(14)
_cell_angle_gamma                118.9930(13)
_cell_volume                     520.10(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9381
_cell_measurement_theta_min      3.2448
_cell_measurement_theta_max      28.3129
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.110
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             238

_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;

Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              Incoatec
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer optics'

_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 SMART APEXII'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            15215
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             2576
_reflns_number_gt                2331
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0946
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.088
_refine_ls_number_reflns         2576
_refine_ls_number_parameters     164
_refine_ls_number_restraints     32
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0465P)²+0.3214P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.413
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker APEX4'
_computing_data_reduction        'Bruker APEX4'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond (Brakdenburg 2014)'
_computing_publication_material  'Bruker APEX4'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.47626(5) 0.39943(5) 0.19644(3) 0.01256(11) Uani d . . . 1.000000 . .
O O1 0.65829(16) 0.47317(16) 0.13758(9) 0.0157(2) Uani d . . . 1.000000 . .
O O2 0.35070(16) 0.16376(16) 0.17212(9) 0.0158(2) Uani d . . . 1.000000 . .
O O3 0.34377(16) 0.49188(16) 0.17000(9) 0.0165(2) Uani d . . D 1.000000 . .
N N1 0.8757(2) 0.2274(2) 0.11120(12) 0.0182(3) Uani d . . . 1.000000 . .
H H1A 0.805340 0.296938 0.109994 0.022000 Uiso calc U . R 1.000000 . .
H H1B 1.012919 0.294262 0.109458 0.022000 Uiso calc U . R 1.000000 . .
N N2 0.56764(19) -0.0796(2) 0.11829(11) 0.0169(3) Uani d . . . 1.000000 . .
H H2A 0.500075 -0.216651 0.119946 0.020000 Uiso calc U . R 1.000000 . .
H H2B 0.497947 -0.009269 0.118382 0.020000 Uiso calc U . R 1.000000 . .
N N3 0.8803(2) -0.0844(2) 0.11552(11) 0.0170(3) Uani d . . . 1.000000 . .
H H3A 0.813235 -0.221522 0.117172 0.020000 Uiso calc U . R 1.000000 . .
H H3B 1.017571 -0.017205 0.113778 0.020000 Uiso calc U . R 1.000000 . .
C C1 0.5863(2) 0.4993(2) 0.35267(12) 0.0142(3) Uani d . . . 1.000000 . .
C C2 0.8046(2) 0.6187(3) 0.38828(13) 0.0220(3) Uani d . . . 1.000000 . .
H H2 0.892192 0.644898 0.330325 0.026000 Uiso calc U . R 1.000000 . .
C C3 0.8988(3) 0.7024(3) 0.51096(15) 0.0330(4) Uani d . . . 1.000000 . .
H H3 1.050375 0.785279 0.535415 0.040000 Uiso calc U . R 1.000000 . .
C C4 0.7757(2) 0.6664(3) 0.59517(14) 0.0261(4) Uani d . . . 1.000000 . .
H H4 0.842679 0.724982 0.677571 0.031000 Uiso calc U . R 1.000000 . .
C C5 0.5492(2) 0.5429(2) 0.56192(12) 0.0149(3) Uani d . . . 1.000000 . .
C C6 0.7744(2) 0.0210(2) 0.11567(12) 0.0145(3) Uani d . . . 1.000000 . .
O O4 0.2890(8) 0.7884(9) 0.3603(5) 0.0417(14) Uani d U P D 0.292(2) A -1
H H4A 0.298(6) 0.711(8) 0.299(4) 0.063000 Uiso d U P D 0.292(2) A -1
C C7 0.495(4) 0.966(5) 0.423(2) 0.043(2) Uani d U P D 0.292(2) A -1
H H7A 0.529167 1.091052 0.388808 0.051000 Uiso calc U P R 0.292(2) A -1
H H7B 0.604043 0.924679 0.410360 0.051000 Uiso calc U P R 0.292(2) A -1
C C8 0.508(6) 1.033(6) 0.557(2) 0.043(2) Uani d . P D 0.292(2) A -1
H H8A 0.428131 1.107569 0.570543 0.064000 Uiso calc U P R 0.292(2) A -1
H H8B 0.658189 1.129738 0.597285 0.064000 Uiso calc U P R 0.292(2) A -1
H H8C 0.445955 0.903557 0.587843 0.064000 Uiso calc U P R 0.292(2) A -1
O O4' 0.2908(11) 0.9273(13) 0.3642(7) 0.0375(17) Uani d U P D 0.208(2) B -2
H H4B 0.305(7) 0.990(15) 0.308(7) 0.056000 Uiso d U P D 0.208(2) B -2
C C7' 0.493(3) 1.002(6) 0.440(2) 0.043(2) Uani d . P D 0.208(2) B -2
H H7C 0.597376 1.145793 0.429393 0.051000 Uiso calc U P R 0.208(2) B -2
H H7D 0.543569 0.901917 0.412398 0.051000 Uiso calc U P R 0.208(2) B -2
C C8' 0.494(8) 1.023(9) 0.573(2) 0.043(2) Uani d . P D 0.208(2) B -2
H H8D 0.438009 1.116969 0.600866 0.064000 Uiso calc U P R 0.208(2) B -2
H H8E 0.641312 1.086834 0.616790 0.064000 Uiso calc U P R 0.208(2) B -2
H H8F 0.404441 0.879831 0.585951 0.064000 Uiso calc U P R 0.208(2) B -2


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 . 1.4568(10) ?
S1 O2 . 1.4599(10) ?
S1 O3 . 1.4604(10) ?
S1 C1 . 1.7771(14) ?
N1 C6 . 1.3315(19) ?
N1 H1A . 0.880000 ?
N1 H1B . 0.880000 ?
N2 C6 . 1.3257(19) ?
N2 H2A . 0.880000 ?
N2 H2B . 0.880000 ?
N3 C6 . 1.3285(18) ?
N3 H3A . 0.880000 ?
N3 H3B . 0.880000 ?
C1 C2 . 1.368(2) ?
C1 C5 2_666 1.4305(19) ?
C2 C3 . 1.406(2) ?
C2 H2 . 0.950000 ?
C3 C4 . 1.361(2) ?
C3 H3 . 0.950000 ?
C4 C5 . 1.416(2) ?
C4 H4 . 0.950000 ?
C5 C5 2_666 1.424(3) ?
O4 C7 . 1.429(10) ?
O4 H4A . 0.858(10) ?
C7 C8 . 1.520(9) ?
C7 H7A . 0.990000 ?
C7 H7B . 0.990000 ?
C8 H8A . 0.980000 ?
C8 H8B . 0.980000 ?
C8 H8C . 0.980000 ?
O4' C7' . 1.433(10) ?
O4' H4B . 0.850(9) ?
C7' C8' . 1.517(9) ?
C7' H7C . 0.990000 ?
C7' H7D . 0.990000 ?
C8' H8D . 0.980000 ?
C8' H8E . 0.980000 ?
C8' H8F . 0.980000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O2 . . 112.26(6) ?
O1 S1 O3 . . 112.28(6) ?
O2 S1 O3 . . 112.19(6) ?
O1 S1 C1 . . 105.98(6) ?
O2 S1 C1 . . 106.80(6) ?
O3 S1 C1 . . 106.82(6) ?
C6 N1 H1A . . 120.000000 ?
C6 N1 H1B . . 120.000000 ?
H1A N1 H1B . . 120.000000 ?
C6 N2 H2A . . 120.000000 ?
C6 N2 H2B . . 120.000000 ?
H2A N2 H2B . . 120.000000 ?
C6 N3 H3A . . 120.000000 ?
C6 N3 H3B . . 120.000000 ?
H3A N3 H3B . . 120.000000 ?
C2 C1 C5 . 2_666 121.25(13) ?
C2 C1 S1 . . 117.76(11) ?
C5 C1 S1 2_666 . 120.99(10) ?
C1 C2 C3 . . 119.75(14) ?
C1 C2 H2 . . 120.100000 ?
C3 C2 H2 . . 120.100000 ?
C4 C3 C2 . . 120.89(15) ?
C4 C3 H3 . . 119.600000 ?
C2 C3 H3 . . 119.600000 ?
C3 C4 C5 . . 121.06(14) ?
C3 C4 H4 . . 119.500000 ?
C5 C4 H4 . . 119.500000 ?
C4 C5 C5 . 2_666 118.90(16) ?
C4 C5 C1 . 2_666 122.94(13) ?
C5 C5 C1 2_666 2_666 118.15(16) ?
N2 C6 N3 . . 120.23(13) ?
N2 C6 N1 . . 119.95(13) ?
N3 C6 N1 . . 119.81(13) ?
C7 O4 H4A . . 112.(2) ?
O4 C7 C8 . . 113.0(13) ?
O4 C7 H7A . . 109.000000 ?
C8 C7 H7A . . 109.000000 ?
O4 C7 H7B . . 109.000000 ?
C8 C7 H7B . . 109.000000 ?
H7A C7 H7B . . 107.800000 ?
C7 C8 H8A . . 109.500000 ?
C7 C8 H8B . . 109.500000 ?
H8A C8 H8B . . 109.500000 ?
C7 C8 H8C . . 109.500000 ?
H8A C8 H8C . . 109.500000 ?
H8B C8 H8C . . 109.500000 ?
C7' O4' H4B . . 112.(2) ?
O4' C7' C8' . . 116.1(15) ?
O4' C7' H7C . . 108.300000 ?
C8' C7' H7C . . 108.300000 ?
O4' C7' H7D . . 108.300000 ?
C8' C7' H7D . . 108.300000 ?
H7C C7' H7D . . 107.400000 ?
C7' C8' H8D . . 109.500000 ?
C7' C8' H8E . . 109.500000 ?
H8D C8' H8E . . 109.500000 ?
C7' C8' H8F . . 109.500000 ?
H8D C8' H8F . . 109.500000 ?
H8E C8' H8F . . 109.500000 ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
