# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2026

####################################################################### 
# 
# 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_SA_CD_7
_database_code_depnum_ccdc_archive 'CCDC 2526019'
loop_
_audit_author_name
_audit_author_address
'Werner Kaminsky'
;University of Washington
United States of America
;
_audit_update_record             
;
2026-01-26 deposited with the CCDC.	2026-04-29 downloaded from the CCDC.
;

_audit_creation_date             2024-08-14T14:23:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C20 H16 N6 O2, 2(H2 O)'
_chemical_formula_sum            'C20 H20 N6 O4'
_chemical_formula_weight         408.42

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_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                   19.9418(11)
_cell_length_b                   8.6405(3)
_cell_length_c                   11.5476(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.228(6)
_cell_angle_gamma                90
_cell_volume                     1928.70(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5862
_cell_measurement_theta_min      2
_cell_measurement_theta_max      20
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   HKL-Scalepack
_exptl_absorpt_correction_T_min  0.648
_exptl_absorpt_correction_T_max  0.776
_shelx_estimated_absorpt_T_min   0.97
_shelx_estimated_absorpt_T_max   0.994

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_ub_11      -0.025197
_diffrn_orient_matrix_ub_12      -0.075609
_diffrn_orient_matrix_ub_13      -0.074402
_diffrn_orient_matrix_ub_21      0.12318
_diffrn_orient_matrix_ub_22      0.035995
_diffrn_orient_matrix_ub_23      -0.012308
_diffrn_orient_matrix_ub_31      0.016221
_diffrn_orient_matrix_ub_32      -0.060768
_diffrn_orient_matrix_ub_33      0.047898
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_number            8376
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_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         2.107
_diffrn_reflns_theta_max         28.267
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_reflns_Friedel_coverage         0
_reflns_number_total             2360
_reflns_number_gt                1577
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2019/3
_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+0.4820P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2360
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1311
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.058

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.5 0.9843(3) 0.25 0.0233(5) Uani 1 2 d S T P . .
H1 H 0.500001 1.094207 0.250001 0.028 Uiso 1 2 calc R U P . .
C2 C 0.47316(8) 0.90391(19) 0.33239(14) 0.0212(4) Uani 1 1 d . . . . .
H2 H 0.455491 0.959223 0.389543 0.025 Uiso 1 1 calc R U . . .
C3 C 0.47193(8) 0.74213(19) 0.33197(13) 0.0184(4) Uani 1 1 d . . . . .
C4 C 0.5 0.6620(2) 0.25 0.0185(5) Uani 1 2 d S T P . .
H4 H 0.499999 0.552033 0.249999 0.022 Uiso 1 2 calc R U P . .
C5 C 0.43952(8) 0.65908(18) 0.41523(14) 0.0204(4) Uani 1 1 d . . . . .
H5 H 0.431784 0.710782 0.483384 0.024 Uiso 1 1 calc R U . . .
C6 C 0.37742(8) 0.29497(18) 0.46515(14) 0.0203(4) Uani 1 1 d . . . . .
C7 C 0.34468(8) 0.21891(18) 0.55424(13) 0.0191(4) Uani 1 1 d . . . . .
C8 C 0.32126(8) 0.29594(18) 0.64298(14) 0.0213(4) Uani 1 1 d . . . . .
H8 H 0.324529 0.405353 0.65035 0.026 Uiso 1 1 calc R U . . .
C9 C 0.29303(8) 0.20868(19) 0.72029(14) 0.0233(4) Uani 1 1 d . . . . .
H9 H 0.276395 0.257483 0.781476 0.028 Uiso 1 1 calc R U . . .
C10 C 0.28955(9) 0.0503(2) 0.70685(15) 0.0260(4) Uani 1 1 d . . . . .
H10 H 0.271023 -0.007956 0.761451 0.031 Uiso 1 1 calc R U . . .
C11 C 0.33771(8) 0.05889(19) 0.54778(15) 0.0245(4) Uani 1 1 d . . . . .
H11 H 0.353211 0.006674 0.486772 0.029 Uiso 1 1 calc R U . . .
N1 N 0.42178(7) 0.51768(15) 0.39607(11) 0.0205(3) Uani 1 1 d . . . . .
N2 N 0.39085(7) 0.44855(16) 0.47801(12) 0.0202(3) Uani 1 1 d . . . . .
N3 N 0.31068(8) -0.02655(16) 0.62153(12) 0.0268(4) Uani 1 1 d . . . . .
O1 O 0.39167(6) 0.21757(13) 0.38467(10) 0.0274(3) Uani 1 1 d . . . . .
O2 O 0.36561(8) 0.33748(15) 0.15014(13) 0.0325(4) Uani 1 1 d . . . . .
H2N H 0.3811(10) 0.512(2) 0.5342(18) 0.044(6) Uiso 1 1 d . . . . .
H2O H 0.3421(13) 0.249(3) 0.135(2) 0.067(8) Uiso 1 1 d . . . . .
H2P H 0.3879(16) 0.340(3) 0.225(3) 0.105(12) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.3870(19) 2_655 ?
C1 C2 1.3871(19) . ?
C1 H1 0.95 . ?
C2 C3 1.398(2) . ?
C2 H2 0.95 . ?
C3 C4 1.3963(18) . ?
C3 C5 1.470(2) . ?
C4 H4 0.95 . ?
C5 N1 1.276(2) . ?
C5 H5 0.95 . ?
C6 O1 1.2335(18) . ?
C6 N2 1.355(2) . ?
C6 C7 1.499(2) . ?
C7 C11 1.390(2) . ?
C7 C8 1.395(2) . ?
C8 C9 1.389(2) . ?
C8 H8 0.95 . ?
C9 C10 1.377(2) . ?
C9 H9 0.95 . ?
C10 N3 1.339(2) . ?
C10 H10 0.95 . ?
C11 N3 1.337(2) . ?
C11 H11 0.95 . ?
N1 N2 1.3854(18) . ?
N2 H2N 0.91(2) . ?
O2 H2O 0.89(3) . ?
O2 H2P 0.87(3) . ?

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
C2 C1 C2 119.9(2) 2_655 . ?
C2 C1 H1 120 2_655 . ?
C2 C1 H1 120 . . ?
C1 C2 C3 120.50(15) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 119.25(14) . . ?
C4 C3 C5 121.00(15) . . ?
C2 C3 C5 119.73(13) . . ?
C3 C4 C3 120.5(2) . 2_655 ?
C3 C4 H4 119.7 . . ?
C3 C4 H4 119.7 2_655 . ?
N1 C5 C3 120.11(14) . . ?
N1 C5 H5 119.9 . . ?
C3 C5 H5 119.9 . . ?
O1 C6 N2 122.53(14) . . ?
O1 C6 C7 119.96(14) . . ?
N2 C6 C7 117.51(13) . . ?
C11 C7 C8 117.84(14) . . ?
C11 C7 C6 117.00(14) . . ?
C8 C7 C6 125.16(14) . . ?
C9 C8 C7 118.34(15) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C10 C9 C8 118.96(14) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
N3 C10 C9 124.03(15) . . ?
N3 C10 H10 118 . . ?
C9 C10 H10 118 . . ?
N3 C11 C7 124.47(15) . . ?
N3 C11 H11 117.8 . . ?
C7 C11 H11 117.8 . . ?
C5 N1 N2 116.45(13) . . ?
C6 N2 N1 117.17(13) . . ?
C6 N2 H2N 126.8(12) . . ?
N1 N2 H2N 116.0(12) . . ?
C11 N3 C10 116.34(15) . . ?
H2O O2 H2P 109(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
C2 C1 C2 C3 -1.00(11) 2_655 . . . ?
C1 C2 C3 C4 2.0(2) . . . . ?
C1 C2 C3 C5 -176.35(12) . . . . ?
C2 C3 C4 C3 -0.98(10) . . . 2_655 ?
C5 C3 C4 C3 177.33(16) . . . 2_655 ?
C4 C3 C5 N1 -16.6(2) . . . . ?
C2 C3 C5 N1 161.66(15) . . . . ?
O1 C6 C7 C11 5.8(2) . . . . ?
N2 C6 C7 C11 -173.51(14) . . . . ?
O1 C6 C7 C8 -174.61(15) . . . . ?
N2 C6 C7 C8 6.1(2) . . . . ?
C11 C7 C8 C9 0.6(2) . . . . ?
C6 C7 C8 C9 -178.94(15) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C8 C9 C10 N3 -1.3(3) . . . . ?
C8 C7 C11 N3 -0.7(3) . . . . ?
C6 C7 C11 N3 178.93(15) . . . . ?
C3 C5 N1 N2 -179.25(13) . . . . ?
O1 C6 N2 N1 0.0(2) . . . . ?
C7 C6 N2 N1 179.34(13) . . . . ?
C5 N1 N2 C6 -174.17(14) . . . . ?
C7 C11 N3 C10 -0.3(2) . . . . ?
C9 C10 N3 C11 1.3(3) . . . . ?

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
_geom_hbond_publ_flag
C5 H5 O2 0.95 2.62 3.391(2) 138.4 6_566 yes
N2 H2N O2 0.91(2) 1.95(2) 2.8485(18) 174.6(18) 6_566 yes
O2 H2O N3 0.89(3) 2.02(3) 2.889(2) 166(2) 6 yes
O2 H2P N1 0.87(3) 2.46(3) 3.191(2) 142(3) . yes
O2 H2P O1 0.87(3) 2.11(3) 2.8260(17) 139(3) . yes


#----------------------------------------------------------------------------#
#                   SQUEEZE DETAILS                                          #
#----------------------------------------------------------------------------#

