# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_S1
_database_code_depnum_ccdc_archive 'CCDC 2445546'
loop_
_audit_author_name
_audit_author_address
'Waldemar Maniukiewicz'
;Institute of General and Ecological Chemistry , Lodz University of Technology
Poland
;
_audit_update_record             
;
2025-04-21 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;

#===============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_formula_moiety         'C20 H28 Cu4 N24 O8'
_chemical_formula_structural     ?
_chemical_formula_sum            'C20 H28 Cu4 N24 O8'
_chemical_formula_iupac          ?
_chemical_formula_weight         986.86

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'
Cu Cu 0.3201 1.2651 ' 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'

#===============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   8.3413(3)
_cell_length_b                   8.5591(3)
_cell_length_c                   12.6987(4)
_cell_angle_alpha                107.43(2)
_cell_angle_beta                 104.455(2)
_cell_angle_gamma                93.150(2)
_cell_volume                     829.30(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    100
_cell_measurement_reflns_used    20272
_cell_measurement_theta_min      3.7150
_cell_measurement_theta_max      32.6050
_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_exptl_crystal_density_diffrn    1.976
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    2.616
_exptl_absorpt_correction_T_min  0.399
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
#===============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'Pilatus 300K'
_diffrn_detector_area_resol_mean 5.8140

# number of measured reflections (redundant set)
_diffrn_reflns_number            19085
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.47
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998

# number of unique reflections
_reflns_number_total             2983
# number of observed reflections (> n sig(I))
_reflns_number_gt                2917
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'

#===============================================================================

# REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'W=1/[Σ²(FO²)+(0.0324P)²+2.5968P] WHERE P=(FO²+2FC²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2983
_refine_ls_number_parameters     262
_refine_ls_number_restraints     3
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.905
_refine_diff_density_min         -0.702
_refine_diff_density_rms         0.091

#===============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu Uani 0.24894(4) 0.53981(4) 0.43682(3) 1.000 0.0140(1) d . . .
Cu2 Cu Uani 0.75048(5) 0.92173(5) 0.63039(3) 1.000 0.0196(1) d . . .
O1 O Uani 0.2128(3) 0.5372(3) 0.28119(19) 1.000 0.0267(7) d . . .
O2 O Uani 0.4957(3) 0.6824(3) 0.9858(2) 1.000 0.0356(9) d . . .
O3 O Uani 0.7464(3) 0.9409(3) 0.79381(19) 1.000 0.0240(7) d . . .
O4 O Uani 0.0334(3) 0.6948(2) 0.44706(15) 1.000 0.0238(7) d D . .
N1 N Uani 0.2754(3) 0.5282(3) 0.5911(2) 1.000 0.0166(7) d . . .
N2 N Uani 0.3936(3) 0.5928(3) 0.7911(2) 1.000 0.0185(7) d . . .
N3 N Uani 0.6196(4) 0.8139(4) 0.8903(2) 1.000 0.0265(9) d . . .
N4 N Uani 0.5362(3) 0.7770(3) 0.5981(2) 1.000 0.0170(7) d . . .
N5 N Uani 0.4446(3) 0.7164(3) 0.4919(2) 1.000 0.0168(7) d . . .
N6 N Uani 0.6522(3) 0.8901(3) 0.4713(2) 1.000 0.0186(8) d . . .
N7 N Uani 0.1059(3) 0.3130(3) 0.3705(2) 1.000 0.0183(8) d . . .
N8 N Uani 0.0171(3) 0.2793(3) 0.2724(2) 1.000 0.0245(9) d . . .
N9 N Uani -0.0680(4) 0.2448(4) 0.1794(3) 1.000 0.0379(10) d . . .
N10 N Uani 0.9562(4) 1.0734(3) 0.6680(3) 1.000 0.0271(9) d . . .
N11 N Uani 1.0939(4) 1.0307(3) 0.6903(2) 1.000 0.0261(9) d . . .
N12 N Uani 1.2297(4) 0.9962(4) 0.7108(3) 1.000 0.0332(10) d . . .
C1 C Uani 0.3850(4) 0.6135(4) 0.6857(3) 1.000 0.0165(8) d . . .
C2 C Uani 0.5011(4) 0.6957(4) 0.8944(3) 1.000 0.0239(10) d . . .
C3 C Uani 0.6339(4) 0.8360(4) 0.7924(3) 1.000 0.0213(9) d . . .
C4 C Uani 0.5114(4) 0.7370(4) 0.6862(3) 1.000 0.0164(8) d . . .
C5 C Uani 0.2823(4) 0.4574(4) 0.7969(3) 1.000 0.0258(10) d . . .
C6 C Uani 0.7376(6) 0.9193(6) 0.9997(3) 1.000 0.0451(15) d . . .
C7 C Uani 0.5094(4) 0.7904(4) 0.4217(3) 1.000 0.0180(9) d . . .
C8 C Uani 0.4186(4) 0.7577(4) 0.3058(3) 1.000 0.0209(9) d . . .
C9 C Uani 0.2806(4) 0.6395(4) 0.2440(3) 1.000 0.0224(9) d . . .
C10 C Uani 0.1986(5) 0.6239(5) 0.1203(3) 1.000 0.0327(11) d . . .
H1 H Uiso 0.20280 0.45500 0.59708 1.000 0.0200 c RU . .
H4A H Uiso 0.0176(8) 0.7318(19) 0.5123(3) 1.000 0.0360 d DU . .
H4B H Uiso 0.043(2) 0.7725(4) 0.4204(4) 1.000 0.0360 d DU . .
H5A H Uiso 0.16903 0.48698 0.78885 1.000 0.0390 c RU . .
H5B H Uiso 0.32379 0.43957 0.87112 1.000 0.0390 c RU . .
H5C H Uiso 0.28006 0.35583 0.73467 1.000 0.0390 c RU . .
H6 H Uiso 0.69989 0.93957 0.43303 1.000 0.0220 c RU . .
H6A H Uiso 0.84723 0.88102 1.00746 1.000 0.0680 c RU . .
H6B H Uiso 0.69566 0.91261 1.06398 1.000 0.0680 c RU . .
H6C H Uiso 0.74824 1.03414 1.00024 1.000 0.0680 c RU . .
H8 H Uiso 0.45633 0.82373 0.26614 1.000 0.0250 c RU . .
H10A H Uiso 0.27479 0.68117 0.09187 1.000 0.0490 c RU . .
H10B H Uiso 0.09506 0.67353 0.11515 1.000 0.0490 c RU . .
H10C H Uiso 0.17287 0.50667 0.07355 1.000 0.0490 c RU . .


#===============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.916(2) .
Cu1 O4 2.299(2) .
Cu1 N1 1.949(2) .
Cu1 N5 1.991(3) .
Cu1 N7 2.041(3) .
Cu2 O3 2.041(2) .
Cu2 N4 1.996(3) .
Cu2 N6 1.910(2) .
Cu2 N10 1.958(3) .
Cu2 N7 2.394(3) 2_666
Cu2 N8 2.947(3) 2_666
O1 C9 1.279(4) .
O2 C2 1.211(4) .
O3 C3 1.256(4) .
N1 C1 1.290(4) .
N2 C1 1.387(4) .
N2 C2 1.391(4) .
N2 C5 1.476(4) .
N3 C2 1.397(5) .
N3 C3 1.345(4) .
N3 C6 1.477(5) .
N4 N5 1.302(3) .
N4 C4 1.322(4) .
O4 H4A 0.840(5) .
O4 H4B 0.840(5) .
N5 C7 1.425(4) .
N6 C7 1.317(4) .
N7 N8 1.218(3) .
N8 N9 1.156(4) .
N10 N11 1.216(5) .
N11 N12 1.172(5) .
N1 H1 0.8800 .
C1 C4 1.449(5) .
C3 C4 1.454(5) .
N6 H6 0.8800 .
C7 C8 1.411(5) .
C8 C9 1.382(5) .
C9 C10 1.510(5) .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C8 H8 0.9500 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 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
O1 Cu1 O4 87.60(9) . .
O1 Cu1 N1 176.08(11) . .
O1 Cu1 N5 91.86(11) . .
O1 Cu1 N7 86.67(11) . .
O4 Cu1 N1 92.59(9) . .
O4 Cu1 N5 101.14(9) . .
O4 Cu1 N7 97.02(9) . .
N1 Cu1 N5 91.95(10) . .
N1 Cu1 N7 89.41(10) . .
N5 Cu1 N7 161.71(11) . .
O3 Cu2 N4 79.64(10) . .
O3 Cu2 N6 154.78(11) . .
O3 Cu2 N10 98.38(13) . .
O3 Cu2 N7 87.42(10) . 2_666
O3 Cu2 N8 68.47(9) . 2_666
N4 Cu2 N6 78.22(11) . .
N4 Cu2 N10 176.80(12) . .
N4 Cu2 N7 88.77(10) . 2_666
N4 Cu2 N8 98.61(9) . 2_666
N6 Cu2 N10 103.17(13) . .
N6 Cu2 N7 103.96(10) . 2_666
N6 Cu2 N8 126.86(9) . 2_666
N7 Cu2 N10 93.67(11) 2_666 .
N8 Cu2 N10 82.90(10) 2_666 .
N7 Cu2 N8 23.58(7) 2_666 2_666
Cu1 O1 C9 128.2(2) . .
Cu2 O3 C3 110.5(2) . .
Cu1 N1 C1 128.7(2) . .
C1 N2 C2 123.4(3) . .
C1 N2 C5 119.6(3) . .
C2 N2 C5 117.0(3) . .
C2 N3 C3 123.8(3) . .
C2 N3 C6 118.1(3) . .
C3 N3 C6 118.1(3) . .
Cu2 N4 N5 117.9(2) . .
Cu2 N4 C4 115.6(2) . .
N5 N4 C4 126.1(3) . .
Cu1 O4 H4A 115.8(8) . .
Cu1 O4 H4B 111.5(11) . .
H4A O4 H4B 109.7(12) . .
N4 N5 C7 109.9(3) . .
Cu1 N5 C7 125.7(2) . .
Cu1 N5 N4 124.4(2) . .
Cu2 N6 C7 116.6(2) . .
Cu1 N7 Cu2 116.92(11) . 2_666
Cu1 N7 N8 115.5(2) . .
Cu2 N7 N8 104.64(19) 2_666 .
N7 N8 N9 178.9(3) . .
Cu2 N8 N7 51.79(16) 2_666 .
Cu2 N8 N9 127.5(2) 2_666 .
Cu2 N10 N11 122.2(2) . .
N10 N11 N12 176.7(3) . .
N1 C1 N2 123.8(3) . .
N1 C1 C4 120.5(3) . .
N2 C1 C4 115.8(3) . .
Cu1 N1 H1 116.00 . .
C1 N1 H1 116.00 . .
O2 C2 N2 121.6(3) . .
O2 C2 N3 120.2(3) . .
N2 C2 N3 118.1(3) . .
O3 C3 N3 120.9(3) . .
N3 C3 C4 117.2(3) . .
O3 C3 C4 121.8(3) . .
N4 C4 C3 110.6(3) . .
C1 C4 C3 121.1(3) . .
N4 C4 C1 128.4(3) . .
Cu2 N6 H6 122.00 . .
C7 N6 H6 122.00 . .
N5 C7 N6 116.7(3) . .
N5 C7 C8 119.7(3) . .
N6 C7 C8 123.6(3) . .
C7 C8 C9 126.8(3) . .
O1 C9 C8 126.1(3) . .
O1 C9 C10 114.8(3) . .
C8 C9 C10 119.1(3) . .
N2 C5 H5A 109.00 . .
N2 C5 H5B 109.00 . .
N2 C5 H5C 110.00 . .
H5A C5 H5B 109.00 . .
H5A C5 H5C 109.00 . .
H5B C5 H5C 109.00 . .
N3 C6 H6A 109.00 . .
N3 C6 H6B 109.00 . .
N3 C6 H6C 109.00 . .
H6A C6 H6B 109.00 . .
H6A C6 H6C 109.00 . .
H6B C6 H6C 109.00 . .
C7 C8 H8 117.00 . .
C9 C8 H8 117.00 . .
C9 C10 H10A 109.00 . .
C9 C10 H10B 110.00 . .
C9 C10 H10C 109.00 . .
H10A C10 H10B 109.00 . .
H10A C10 H10C 109.00 . .
H10B C10 H10C 109.00 . .
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_3
_geom_torsion_site_symmetry_4
O4 Cu1 O1 C9 90.6(3) . . .
N5 Cu1 O1 C9 -10.5(3) . . .
N7 Cu1 O1 C9 -172.2(3) . . .
O4 Cu1 N1 C1 -100.6(3) . . .
N5 Cu1 N1 C1 0.6(3) . . .
N7 Cu1 N1 C1 162.4(3) . . .
O1 Cu1 N5 N4 -178.2(2) . . .
O1 Cu1 N5 C7 -0.8(3) . . .
O4 Cu1 N5 N4 93.9(2) . . .
O4 Cu1 N5 C7 -88.8(3) . . .
N1 Cu1 N5 N4 0.9(3) . . .
N1 Cu1 N5 C7 178.2(3) . . .
O1 Cu1 N7 N8 -19.0(2) . . .
O1 Cu1 N7 Cu2 104.84(13) . . 2_666
O4 Cu1 N7 N8 68.2(2) . . .
O4 Cu1 N7 Cu2 -167.99(10) . . 2_666
N1 Cu1 N7 N8 160.8(2) . . .
N1 Cu1 N7 Cu2 -75.46(13) . . 2_666
N4 Cu2 O3 C3 11.1(2) . . .
N6 Cu2 O3 C3 39.9(4) . . .
N10 Cu2 O3 C3 -171.5(2) . . .
N7 Cu2 O3 C3 -78.2(2) 2_666 . .
N8 Cu2 O3 C3 -92.6(2) 2_666 . .
O3 Cu2 N4 N5 175.1(2) . . .
O3 Cu2 N4 C4 -12.5(2) . . .
N6 Cu2 N4 N5 7.2(2) . . .
N6 Cu2 N4 C4 179.6(3) . . .
N7 Cu2 N4 N5 -97.3(2) 2_666 . .
N7 Cu2 N4 C4 75.1(2) 2_666 . .
N8 Cu2 N4 N5 -118.8(2) 2_666 . .
N8 Cu2 N4 C4 53.6(2) 2_666 . .
O3 Cu2 N6 C7 -32.4(4) . . .
N4 Cu2 N6 C7 -3.4(2) . . .
N10 Cu2 N6 C7 179.6(2) . . .
N7 Cu2 N6 C7 82.4(3) 2_666 . .
N8 Cu2 N6 C7 88.7(3) 2_666 . .
O3 Cu2 N10 N11 82.0(3) . . .
N6 Cu2 N10 N11 -111.2(3) . . .
N7 Cu2 N10 N11 -6.0(3) 2_666 . .
N8 Cu2 N10 N11 15.0(3) 2_666 . .
O3 Cu2 N7 Cu1 93.78(13) . 2_666 2_666
O3 Cu2 N7 N8 -35.4(2) . 2_666 2_666
N4 Cu2 N7 Cu1 14.10(13) . 2_666 2_666
N4 Cu2 N7 N8 -115.1(2) . 2_666 2_666
N6 Cu2 N7 Cu1 -63.44(14) . 2_666 2_666
N6 Cu2 N7 N8 167.4(2) . 2_666 2_666
N10 Cu2 N7 Cu1 -167.98(15) . 2_666 2_666
N10 Cu2 N7 N8 62.8(2) . 2_666 2_666
O3 Cu2 N8 N7 141.5(2) . 2_666 2_666
O3 Cu2 N8 N9 -39.5(3) . 2_666 2_666
N4 Cu2 N8 N7 66.3(2) . 2_666 2_666
N4 Cu2 N8 N9 -114.7(3) . 2_666 2_666
N6 Cu2 N8 N7 -15.4(2) . 2_666 2_666
N6 Cu2 N8 N9 163.6(3) . 2_666 2_666
N10 Cu2 N8 N7 -116.5(2) . 2_666 2_666
N10 Cu2 N8 N9 62.4(3) . 2_666 2_666
Cu1 O1 C9 C8 13.1(5) . . .
Cu1 O1 C9 C10 -167.4(2) . . .
Cu2 O3 C3 N3 172.9(3) . . .
Cu2 O3 C3 C4 -8.9(4) . . .
Cu1 N1 C1 N2 -179.0(2) . . .
Cu1 N1 C1 C4 -0.4(5) . . .
C2 N2 C1 N1 -173.4(3) . . .
C2 N2 C1 C4 7.9(5) . . .
C5 N2 C1 N1 5.4(5) . . .
C5 N2 C1 C4 -173.2(3) . . .
C1 N2 C2 O2 173.8(3) . . .
C1 N2 C2 N3 -7.6(5) . . .
C5 N2 C2 O2 -5.1(5) . . .
C5 N2 C2 N3 173.5(3) . . .
C3 N3 C2 O2 179.8(4) . . .
C3 N3 C2 N2 1.2(5) . . .
C6 N3 C2 O2 0.7(5) . . .
C6 N3 C2 N2 -177.9(3) . . .
C2 N3 C3 O3 -177.8(3) . . .
C2 N3 C3 C4 3.9(5) . . .
C6 N3 C3 O3 1.4(5) . . .
C6 N3 C3 C4 -177.0(4) . . .
Cu2 N4 N5 Cu1 168.77(13) . . .
Cu2 N4 N5 C7 -9.0(3) . . .
C4 N4 N5 Cu1 -2.8(4) . . .
C4 N4 N5 C7 179.5(3) . . .
Cu2 N4 C4 C1 -168.4(3) . . .
Cu2 N4 C4 C3 11.2(4) . . .
N5 N4 C4 C1 3.4(6) . . .
N5 N4 C4 C3 -177.1(3) . . .
Cu1 N5 C7 N6 -171.6(2) . . .
Cu1 N5 C7 C8 9.8(4) . . .
N4 N5 C7 N6 6.1(4) . . .
N4 N5 C7 C8 -172.6(3) . . .
Cu2 N6 C7 N5 -0.4(4) . . .
Cu2 N6 C7 C8 178.2(3) . . .
Cu1 N7 N8 Cu2 130.0(2) . . 2_666
N1 C1 C4 N4 -1.6(6) . . .
N1 C1 C4 C3 178.9(3) . . .
N2 C1 C4 N4 177.1(3) . . .
N2 C1 C4 C3 -2.4(5) . . .
O3 C3 C4 N4 -1.2(5) . . .
O3 C3 C4 C1 178.4(3) . . .
N3 C3 C4 N4 177.2(3) . . .
N3 C3 C4 C1 -3.3(5) . . .
N5 C7 C8 C9 -10.5(6) . . .
N6 C7 C8 C9 171.0(3) . . .
C7 C8 C9 O1 -1.2(6) . . .
C7 C8 C9 C10 179.4(4) . . .
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
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N1 H1 O4 0.8800 2.1400 2.966(3) 156.00 2_566
O4 H4A N7 0.840(5) 2.118(9) 2.855(3) 146.2(13) 2_566
O4 H4B N10 0.840(5) 1.972(5) 2.804(4) 170.1(7) 2_676
N6 H6 N12 0.8800 2.2500 3.106(4) 162.00 2_776


#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_SN1
_database_code_depnum_ccdc_archive 'CCDC 2445548'
loop_
_audit_author_name
_audit_author_address
'Waldemar Maniukiewicz'
;Institute of General and Ecological Chemistry , Lodz University of Technology
Poland
;
_audit_update_record             
;
2025-04-21 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;

#===============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C10 H12 N6 O3), H2 O'
_chemical_formula_structural     ?
_chemical_formula_sum            'C20 H26 N12 O7'
_chemical_formula_iupac          ?
_chemical_formula_weight         546.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 ' 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 0.0311 0.0180 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_Int_Tables_number      15

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+z

_cell_length_a                   20.8768(5)
_cell_length_b                   5.8611(1)
_cell_length_c                   19.6178(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.741(2)
_cell_angle_gamma                90
_cell_volume                     2392.24(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    23579
_cell_measurement_theta_min      4.249
_cell_measurement_theta_max      78.907
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_F_000             1144
_exptl_absorpt_coefficient_mu    1.006
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;

#===============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'Pilatus 300K'
_diffrn_detector_area_resol_mean 5.814

# number of measured reflections (redundant set)
_diffrn_reflns_number            28635
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.25
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_full        66.60
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             2109
# number of observed reflections (> n sig(I))
_reflns_number_gt                2042
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#===============================================================================

# REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0277P)²+2.6302P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'shelxl-2018/3 (sheldrick 2018)'
_refine_ls_extinction_coef       0.00091(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2109
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0680
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.036

#===============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O Uani 0.42354(4) -0.22117(14) 0.52320(4) 1.000 0.0170(3) d . . .
O2 O Uani 0.40764(4) 0.64572(15) 0.74370(4) 1.000 0.0183(3) d . . .
O3 O Uani 0.24762(4) 1.15792(14) 0.70265(4) 1.000 0.0168(3) d . . .
N1 N Uani 0.37464(4) -0.05610(17) 0.52056(5) 1.000 0.0159(3) d . . .
N2 N Uani 0.34790(4) 0.26453(17) 0.58065(5) 1.000 0.0137(3) d . . .
N3 N Uani 0.36878(4) 0.39232(16) 0.63158(5) 1.000 0.0128(3) d . . .
N4 N Uani 0.33288(4) 0.91658(16) 0.71644(5) 1.000 0.0126(3) d . . .
N5 N Uani 0.24655(4) 0.84639(17) 0.63328(5) 1.000 0.0130(3) d . . .
N6 N Uani 0.24528(5) 0.52706(18) 0.56344(5) 1.000 0.0146(3) d . . .
C1 C Uani 0.52160(6) -0.3324(2) 0.58865(6) 1.000 0.0208(4) d . . .
C2 C Uani 0.46705(5) -0.1708(2) 0.57698(6) 1.000 0.0149(3) d . . .
C3 C Uani 0.44920(5) 0.0200(2) 0.60886(6) 1.000 0.0141(3) d . . .
C4 C Uani 0.39060(5) 0.0845(2) 0.57142(5) 1.000 0.0128(3) d . . .
O4 O Uani 0.50000 0.2960(2) 0.75000 1.000 0.0201(4) d STP . .
C5 C Uani 0.33385(5) 0.57710(19) 0.64719(5) 1.000 0.0126(3) d . . .
C6 C Uani 0.36155(5) 0.7064(2) 0.70537(6) 1.000 0.0131(3) d . . .
C7 C Uani 0.27435(5) 0.9855(2) 0.68602(5) 1.000 0.0127(3) d . . .
C8 C Uani 0.27438(5) 0.64877(19) 0.61344(5) 1.000 0.0123(3) d . . .
C9 C Uani 0.36061(5) 1.0532(2) 0.77401(6) 1.000 0.0159(3) d . . .
C10 C Uani 0.18443(5) 0.9206(2) 0.59964(6) 1.000 0.0165(3) d . . .
H1A H Uiso 0.50506 -0.48858 0.59033 1.000 0.0310 c RU . .
H1B H Uiso 0.54605 -0.29604 0.63209 1.000 0.0310 c RU . .
H1C H Uiso 0.54970 -0.31918 0.55123 1.000 0.0310 c RU . .
H2 H Uiso 0.47068 0.09408 0.64730 1.000 0.0170 c RU . .
H6A H Uiso 0.2064(8) 0.562(3) 0.5422(8) 1.000 0.029(4) d . . .
H6B H Uiso 0.2658(7) 0.399(3) 0.5532(7) 1.000 0.026(4) d . . .
H9A H Uiso 0.34442 0.99804 0.81650 1.000 0.0240 c RU . .
H9B H Uiso 0.34843 1.21348 0.76692 1.000 0.0240 c RU . .
H9C H Uiso 0.40755 1.03963 0.77714 1.000 0.0240 c RU . .
H10A H Uiso 0.18915 0.95124 0.55120 1.000 0.0250 c RU . .
H10B H Uiso 0.17038 1.05990 0.62169 1.000 0.0250 c RU . .
H10C H Uiso 0.15239 0.80022 0.60363 1.000 0.0250 c RU . .
H4 H Uiso 0.4671(8) 0.391(3) 0.7428(9) 1.000 0.045(5) d . . .


#===============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.4043(12)
O1 C2 1.3664(14)
O2 C6 1.2240(14)
O3 C7 1.2121(14)
N1 C4 1.3156(14)
N2 N3 1.2951(14)
N2 C4 1.4027(15)
N3 C5 1.3548(14)
N4 C6 1.3944(15)
N4 C7 1.3755(14)
N4 C9 1.4642(15)
N5 C7 1.4046(14)
N5 C8 1.3668(15)
N5 C10 1.4714(14)
N6 C8 1.3197(14)
C1 C2 1.4844(16)
C2 C3 1.3488(16)
C3 C4 1.4250(15)
C5 C6 1.4500(15)
C5 C8 1.4214(15)
N6 H6A 0.905(17)
N6 H6B 0.895(17)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C3 H2 0.9500
O4 H4 0.886(17)
O4 H4 0.886(17)
C9 H9B 0.9800
C9 H9C 0.9800
C9 H9A 0.9800
C10 H10C 0.9800
C10 H10A 0.9800
C10 H10B 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_3
N1 O1 C2 108.33(8) .
O1 N1 C4 105.42(8) .
N3 N2 C4 110.96(8) .
N2 N3 C5 118.92(9) .
C6 N4 C7 124.70(9) .
C6 N4 C9 117.12(9) .
C7 N4 C9 117.03(9) .
C7 N5 C8 122.83(9) .
C7 N5 C10 117.00(9) .
C8 N5 C10 120.16(9) .
O1 C2 C1 115.71(10) .
O1 C2 C3 110.22(10) .
C1 C2 C3 134.06(11) .
C2 C3 C4 103.85(10) .
N1 C4 N2 116.44(9) .
N1 C4 C3 112.18(10) .
N2 C4 C3 131.36(10) .
N3 C5 C6 114.12(9) .
N3 C5 C8 126.64(10) .
C6 C5 C8 119.24(10) .
O2 C6 N4 119.13(10) .
O2 C6 C5 125.02(11) .
N4 C6 C5 115.85(9) .
C8 N6 H6B 114.9(9) .
H6A N6 H6B 120.9(14) .
C8 N6 H6A 124.1(11) .
N4 C7 N5 116.57(10) .
O3 C7 N4 122.71(10) .
O3 C7 N5 120.72(10) .
N5 C8 N6 119.30(10) .
N5 C8 C5 119.56(9) .
N6 C8 C5 121.14(10) .
C2 C1 H1A 109.00 .
C2 C1 H1B 109.00 .
C2 C1 H1C 109.00 .
H1A C1 H1B 109.00 .
H1A C1 H1C 109.00 .
H1B C1 H1C 109.00 .
C2 C3 H2 128.00 .
C4 C3 H2 128.00 .
H4 O4 H4 102.2(16) 2_656
N4 C9 H9A 109.00 .
N4 C9 H9B 109.00 .
H9A C9 H9B 109.00 .
H9A C9 H9C 109.00 .
N4 C9 H9C 109.00 .
H9B C9 H9C 109.00 .
N5 C10 H10B 109.00 .
N5 C10 H10C 109.00 .
N5 C10 H10A 109.00 .
H10A C10 H10C 109.00 .
H10B C10 H10C 109.00 .
H10A C10 H10B 109.00 .

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
C2 O1 N1 C4 0.41(11)
N1 O1 C2 C1 178.46(9)
N1 O1 C2 C3 -0.69(12)
O1 N1 C4 N2 -178.66(9)
O1 N1 C4 C3 -0.02(14)
C4 N2 N3 C5 179.01(9)
N3 N2 C4 N1 -179.43(9)
N3 N2 C4 C3 2.23(16)
N2 N3 C5 C6 179.56(9)
N2 N3 C5 C8 0.73(16)
C7 N4 C6 O2 -167.03(10)
C7 N4 C6 C5 13.86(15)
C9 N4 C6 O2 0.31(15)
C9 N4 C6 C5 -178.81(9)
C6 N4 C7 O3 171.37(11)
C6 N4 C7 N5 -9.33(15)
C9 N4 C7 O3 4.02(15)
C9 N4 C7 N5 -176.67(9)
C8 N5 C7 O3 -178.99(10)
C8 N5 C7 N4 1.69(15)
C10 N5 C7 O3 0.29(15)
C10 N5 C7 N4 -179.03(9)
C7 N5 C8 N6 179.97(11)
C7 N5 C8 C5 0.35(15)
C10 N5 C8 N6 0.71(15)
C10 N5 C8 C5 -178.91(10)
O1 C2 C3 C4 0.65(12)
C1 C2 C3 C4 -178.27(12)
C2 C3 C4 N1 -0.40(13)
C2 C3 C4 N2 177.99(11)
N3 C5 C6 O2 -8.91(16)
N3 C5 C6 N4 170.14(9)
C8 C5 C6 O2 170.01(11)
C8 C5 C6 N4 -10.94(15)
N3 C5 C8 N5 -176.76(10)
N3 C5 C8 N6 3.63(17)
C6 C5 C8 N5 4.46(15)
C6 C5 C8 N6 -175.14(10)

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
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
O4 H4 O2 0.886(17) 1.943(17) 2.8098(12) 165.6(16) .
N6 H6A N1 0.905(17) 2.009(16) 2.8862(14) 163.0(16) 7_556
N6 H6B N2 0.895(17) 1.923(15) 2.6366(14) 135.5(13) .
C1 H1B O2 0.9800 2.5700 3.4947(14) 158.00 2_646
C3 H2 O4 0.9500 2.3700 3.3050(13) 167.00 .
C9 H9C O4 0.9800 2.5400 3.3078(12) 135.00 1_565


#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMF'
####################################################################### 
# 
# 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_S3
_database_code_depnum_ccdc_archive 'CCDC 2445547'
loop_
_audit_author_name
_audit_author_address
'Waldemar Maniukiewicz'
;Institute of General and Ecological Chemistry , Lodz University of Technology
Poland
;
_audit_update_record             
;
2025-04-21 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;

#===============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_formula_moiety         'C10 H10 N6 O3'
_chemical_formula_structural     ?
_chemical_formula_sum            'C10 H10 N6 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         262.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 ' 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 0.0311 0.0180 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   13.5715(1)
_cell_length_b                   12.1653(1)
_cell_length_c                   6.7738(1)
_cell_angle_alpha                90
_cell_angle_beta                 99.392(1)
_cell_angle_gamma                90
_cell_volume                     1103.37(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    31327
_cell_measurement_theta_min      4.8750
_cell_measurement_theta_max      79.1950
_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.190
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    1.035
_exptl_absorpt_correction_T_min  0.349
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.68a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
#===============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'Pilatus 300K'
_diffrn_detector_area_resol_mean 5.8140

# number of measured reflections (redundant set)
_diffrn_reflns_number            38496
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0096
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.30
_diffrn_reflns_theta_max         67.73
_diffrn_reflns_theta_full        67.68
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998

# number of unique reflections
_reflns_number_total             1994
# number of observed reflections (> n sig(I))
_reflns_number_gt                1965
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'

#===============================================================================

# REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'W=1/[Σ²(FO²)+(0.0500P)²+0.4836P] WHERE P=(FO²+2FC²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1994
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0893
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.042

#===============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O Uani 0.78479(6) 1.08496(7) 0.53737(13) 1.000 0.0226(3) d . . .
O2 O Uani 0.86540(6) 0.47521(7) 0.63829(13) 1.000 0.0231(3) d . . .
O3 O Uani 0.54963(7) 0.41519(7) 0.29922(14) 1.000 0.0273(3) d . . .
N1 N Uani 0.72874(8) 0.98956(9) 0.48010(17) 1.000 0.0220(3) d . . .
N2 N Uani 0.75975(8) 0.80003(8) 0.51126(15) 1.000 0.0175(3) d . . .
N3 N Uani 0.66838(7) 0.77395(8) 0.40853(15) 1.000 0.0183(3) d . . .
N4 N Uani 0.81925(8) 0.71707(8) 0.58220(15) 1.000 0.0185(3) d . . .
N5 N Uani 0.70527(8) 0.44782(8) 0.47499(15) 1.000 0.0203(3) d . . .
N6 N Uani 0.59741(8) 0.59367(9) 0.33805(15) 1.000 0.0198(3) d . . .
C1 C Uani 0.79107(9) 0.90996(10) 0.54247(17) 1.000 0.0179(3) d . . .
C2 C Uani 0.88558(9) 0.94543(10) 0.63933(18) 1.000 0.0198(3) d . . .
C3 C Uani 0.87736(9) 1.05640(10) 0.63137(18) 1.000 0.0204(3) d . . .
C4 C Uani 0.94601(10) 1.14742(11) 0.7053(2) 1.000 0.0266(4) d . . .
C5 C Uani 0.76288(9) 0.62948(10) 0.52377(17) 1.000 0.0181(3) d . . .
C6 C Uani 0.78626(9) 0.51337(10) 0.55514(18) 1.000 0.0189(3) d . . .
C7 C Uani 0.61265(10) 0.48202(10) 0.36522(18) 1.000 0.0210(3) d . . .
C8 C Uani 0.67087(9) 0.66476(10) 0.41847(17) 1.000 0.0177(3) d . . .
C9 C Uani 0.71709(10) 0.32854(10) 0.5012(2) 1.000 0.0255(4) d . . .
C10 C Uani 0.50509(9) 0.63214(11) 0.21315(19) 1.000 0.0239(4) d . . .
H2 H Uiso 0.94133 0.90217 0.69619 1.000 0.0240 c RU . .
H4A H Uiso 0.95874 1.19229 0.59196 1.000 0.0400 c RU . .
H4B H Uiso 1.00917 1.11708 0.77467 1.000 0.0400 c RU . .
H4C H Uiso 0.91556 1.19313 0.79813 1.000 0.0400 c RU . .
H9A H Uiso 0.65566 0.29720 0.53605 1.000 0.0380 c RU . .
H9B H Uiso 0.77301 0.31328 0.60871 1.000 0.0380 c RU . .
H9C H Uiso 0.73050 0.29549 0.37633 1.000 0.0380 c RU . .
H10A H Uiso 0.51101 0.62414 0.07160 1.000 0.0360 c RU . .
H10B H Uiso 0.49410 0.70964 0.24248 1.000 0.0360 c RU . .
H10C H Uiso 0.44856 0.58829 0.24205 1.000 0.0360 c RU . .


#===============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.4070(14)
O1 C3 1.3577(15)
O2 C6 1.2202(15)
O3 C7 1.2114(16)
N1 C1 1.3096(16)
N2 N3 1.3568(14)
N2 N4 1.3323(14)
N2 C1 1.4087(16)
N3 C8 1.3302(16)
N4 C5 1.3336(16)
N5 C6 1.3943(16)
N5 C7 1.4146(17)
N5 C9 1.4675(16)
N6 C7 1.3817(16)
N6 C8 1.3643(16)
N6 C10 1.4692(17)
C1 C2 1.4097(17)
C2 C3 1.3549(17)
C3 C4 1.4808(18)
C5 C6 1.4557(17)
C5 C8 1.4006(17)
C2 H2 0.9500
C4 H4A 0.9800
C4 H4B 0.9800
C4 H4C 0.9800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 O1 C3 109.60(9)
O1 N1 C1 103.25(10)
N3 N2 N4 117.21(9)
N3 N2 C1 121.81(10)
N4 N2 C1 120.98(10)
N2 N3 C8 101.19(9)
N2 N4 C5 102.34(10)
C6 N5 C7 127.80(10)
C6 N5 C9 117.05(10)
C7 N5 C9 115.13(10)
C7 N6 C8 119.09(11)
C7 N6 C10 119.01(11)
C8 N6 C10 121.80(11)
N1 C1 N2 119.36(11)
N1 C1 C2 114.49(11)
N2 C1 C2 126.14(11)
C1 C2 C3 102.93(11)
O1 C3 C2 109.73(11)
O1 C3 C4 116.76(11)
C2 C3 C4 133.51(12)
N4 C5 C6 129.14(11)
N4 C5 C8 109.08(11)
C6 C5 C8 121.78(11)
O2 C6 N5 122.73(11)
O2 C6 C5 126.23(11)
N5 C6 C5 111.03(10)
O3 C7 N5 120.66(11)
O3 C7 N6 121.96(12)
N5 C7 N6 117.39(11)
N3 C8 N6 127.01(11)
N3 C8 C5 110.18(11)
N6 C8 C5 122.81(11)
C1 C2 H2 129.00
C3 C2 H2 129.00
C3 C4 H4A 109.00
C3 C4 H4B 109.00
C3 C4 H4C 109.00
H4A C4 H4B 109.00
H4A C4 H4C 109.00
H4B C4 H4C 109.00
N5 C9 H9A 109.00
N5 C9 H9B 109.00
N5 C9 H9C 109.00
H9A C9 H9B 109.00
H9A C9 H9C 109.00
H9B C9 H9C 109.00
N6 C10 H10A 109.00
N6 C10 H10B 109.00
N6 C10 H10C 109.00
H10A C10 H10B 109.00
H10A C10 H10C 109.00
H10B C10 H10C 109.00
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
C3 O1 N1 C1 -0.21(12)
N1 O1 C3 C2 0.00(14)
N1 O1 C3 C4 -178.93(10)
O1 N1 C1 N2 179.64(10)
O1 N1 C1 C2 0.34(14)
N4 N2 N3 C8 0.74(13)
C1 N2 N3 C8 -179.23(10)
N3 N2 N4 C5 -0.57(13)
C1 N2 N4 C5 179.41(10)
N3 N2 C1 N1 3.64(17)
N3 N2 C1 C2 -177.14(11)
N4 N2 C1 N1 -176.33(11)
N4 N2 C1 C2 2.89(18)
N2 N3 C8 N6 -179.64(11)
N2 N3 C8 C5 -0.59(12)
N2 N4 C5 C6 179.71(12)
N2 N4 C5 C8 0.14(12)
C7 N5 C6 O2 -175.76(12)
C7 N5 C6 C5 3.74(17)
C9 N5 C6 O2 2.36(17)
C9 N5 C6 C5 -178.14(10)
C6 N5 C7 O3 177.85(12)
C6 N5 C7 N6 -2.48(18)
C9 N5 C7 O3 -0.30(17)
C9 N5 C7 N6 179.37(11)
C8 N6 C7 O3 179.13(12)
C8 N6 C7 N5 -0.54(16)
C10 N6 C7 O3 -4.54(18)
C10 N6 C7 N5 175.79(10)
C7 N6 C8 N3 -179.31(12)
C7 N6 C8 C5 1.74(17)
C10 N6 C8 N3 4.46(19)
C10 N6 C8 C5 -174.48(11)
N1 C1 C2 C3 -0.34(15)
N2 C1 C2 C3 -179.59(11)
C1 C2 C3 O1 0.18(13)
C1 C2 C3 C4 178.87(13)
N4 C5 C6 O2 -2.4(2)
N4 C5 C6 N5 178.16(12)
C8 C5 C6 O2 177.16(12)
C8 C5 C6 N5 -2.32(16)
N4 C5 C8 N3 0.31(14)
N4 C5 C8 N6 179.41(11)
C6 C5 C8 N3 -179.30(11)
C6 C5 C8 N6 -0.20(18)


#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMF'
