# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2309034'
loop_
_audit_author_name
_audit_author_address
'ZongWen Mo'
;Wuyi University
China
;
_audit_update_record             
;
2023-11-18 deposited with the CCDC.	2024-05-16 downloaded from the CCDC.
;
_audit_creation_date             2023-11-18
_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         'C24 H18 Cu3 N9 O1, 0.333(N3 O3)'
_chemical_formula_sum            'C24 H18 Cu3 N10 O2'
_chemical_formula_weight         669.10
_chemical_absolute_configuration ?
_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 0.0181 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'
Cu Cu -1.9646 0.5888 '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'

_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      cubic
_space_group_IT_number           220
_space_group_name_H-M_alt        'I -4 3 d'
_space_group_name_Hall           'I -4bd 2c 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'z, x, y'
'z+1/2, -x+1/2, -y'
'-z+1/2, -x, y+1/2'
'-z, x+1/2, -y+1/2'
'y, z, x'
'-y, z+1/2, -x+1/2'
'y+1/2, -z+1/2, -x'
'-y+1/2, -z, x+1/2'
'y+1/4, x+1/4, z+1/4'
'-y+1/4, -x+3/4, z+3/4'
'y+3/4, -x+1/4, -z+3/4'
'-y+3/4, x+3/4, -z+1/4'
'x+1/4, z+1/4, y+1/4'
'-x+3/4, z+3/4, -y+1/4'
'-x+1/4, -z+3/4, y+3/4'
'x+3/4, -z+1/4, -y+3/4'
'z+1/4, y+1/4, x+1/4'
'z+3/4, -y+1/4, -x+3/4'
'-z+3/4, y+3/4, -x+1/4'
'-z+1/4, -y+3/4, x+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-x+1/2, y+1, -z+1'
'x+1, -y+1, -z+1/2'
'z+1/2, x+1/2, y+1/2'
'z+1, -x+1, -y+1/2'
'-z+1, -x+1/2, y+1'
'-z+1/2, x+1, -y+1'
'y+1/2, z+1/2, x+1/2'
'-y+1/2, z+1, -x+1'
'y+1, -z+1, -x+1/2'
'-y+1, -z+1/2, x+1'
'y+3/4, x+3/4, z+3/4'
'-y+3/4, -x+5/4, z+5/4'
'y+5/4, -x+3/4, -z+5/4'
'-y+5/4, x+5/4, -z+3/4'
'x+3/4, z+3/4, y+3/4'
'-x+5/4, z+5/4, -y+3/4'
'-x+3/4, -z+5/4, y+5/4'
'x+5/4, -z+3/4, -y+5/4'
'z+3/4, y+3/4, x+3/4'
'z+5/4, -y+3/4, -x+5/4'
'-z+5/4, y+5/4, -x+3/4'
'-z+3/4, -y+5/4, x+5/4'

_cell_length_a                   28.8469(4)
_cell_length_b                   28.8469(4)
_cell_length_c                   28.8469(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     24004.8(10)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    3642
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      61.3430
_cell_measurement_theta_min      3.7320
_shelx_estimated_absorpt_T_max   0.873
_shelx_estimated_absorpt_T_min   0.873
_exptl_absorpt_coefficient_mu    1.394
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear bluish blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    0.741
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             5360
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            13693
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.694
_diffrn_reflns_theta_min         3.753
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  17.00   0.50    7.13    --  -48.70  43.00 -39.00   58
  2  ω    -48.00 -22.00   0.50    7.13    --  -48.70  43.00 -39.00   52
  3  ω     35.00  60.00   0.50   28.54    --  107.75 -56.00 -41.00   50
  4  ω    -46.00 -14.00   0.50   28.54    --  -86.25  43.00-157.00   64
  5  ω     38.00  65.00   0.50   28.54    --  107.75 -57.00  30.00   54
  6  ω     39.00  65.00   0.50   28.54    --  107.75 -57.00  90.00   52
  7  ω     35.00  60.00   0.50   28.54    --  107.75 -57.00 -60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0378266000
_diffrn_orient_matrix_UB_12      0.0170724000
_diffrn_orient_matrix_UB_13      0.0336416000
_diffrn_orient_matrix_UB_21      0.0374108000
_diffrn_orient_matrix_UB_22      -0.0229592000
_diffrn_orient_matrix_UB_23      -0.0304528000
_diffrn_orient_matrix_UB_31      0.0047145000
_diffrn_orient_matrix_UB_32      0.0451204000
_diffrn_orient_matrix_UB_33      -0.0281153000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.915
_reflns_Friedel_fraction_max     0.828
_reflns_number_gt                3016
_reflns_number_total             3830
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.022
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.13(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.884
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         3830
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0289
_refine_ls_restrained_S_all      0.885
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0337P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0601
_refine_ls_wR_factor_ref         0.0634
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.87(4)
 0.13(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(O2) \\sim Ueq, Uanis(N4) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N4) \\sim Ueq, Uanis(O2) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 O2, N4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 N4, O2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Others
 Fixed Sof: O2(0.33333)
6.a Aromatic/amide H refined with riding coordinates:
 C4(H), C7(HA), C5(HB), C8(HC), C1(HD), C2(HE)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Cu1 Cu 0.49632(2) 0.98865(2) 0.42748(2) 0.08217(18) Uani 1 1 d . . . . .
O1 O 0.53147(6) 1.03147(6) 0.46853(6) 0.0566(7) Uani 1 3 d S T P . .
N2 N 0.30271(9) 0.79943(8) 0.32108(9) 0.0787(7) Uani 1 1 d . . . . .
N3 N 0.30144(8) 0.82921(9) 0.28633(9) 0.0752(7) Uani 1 1 d . . . . .
N1 N 0.45732(9) 0.94121(9) 0.39549(11) 0.0841(8) Uani 1 1 d . . . . .
C6 C 0.35672(11) 0.85223(11) 0.33403(12) 0.0801(9) Uani 1 1 d . . . . .
C3 C 0.39296(11) 0.88078(11) 0.35417(12) 0.0844(9) Uani 1 1 d . . . . .
C4 C 0.41889(10) 0.91302(10) 0.32829(12) 0.0805(8) Uani 1 1 d . . . . .
H H 0.415083 0.914679 0.296324 0.097 Uiso 1 1 calc R U . . .
C7 C 0.33639(11) 0.81307(12) 0.34933(12) 0.0919(11) Uani 1 1 d . . . . .
HA H 0.344872 0.797553 0.376280 0.110 Uiso 1 1 calc R U . . .
C5 C 0.44917(10) 0.94148(11) 0.34955(15) 0.0863(9) Uani 1 1 d . . . . .
HB H 0.465439 0.962581 0.331396 0.104 Uiso 1 1 calc R U . . .
N4 N 0.46014(15) 0.96014(15) 0.53986(15) 0.123(2) Uani 1 3 d S TU P . .
C8 C 0.33414(11) 0.86176(11) 0.29289(12) 0.0857(10) Uani 1 1 d . . . . .
HC H 0.340477 0.886439 0.273137 0.103 Uiso 1 1 calc R U . . .
C1 C 0.43394(15) 0.90834(14) 0.42128(14) 0.1051(12) Uani 1 1 d . . . . .
HD H 0.438303 0.906983 0.453196 0.126 Uiso 1 1 calc R U . . .
C2 C 0.40556(14) 0.87894(15) 0.40106(14) 0.1070(13) Uani 1 1 d . . . . .
HE H 0.393011 0.855346 0.419093 0.128 Uiso 1 1 calc R U . . .
O2 O 0.4533(4) 0.9868(4) 0.5067(4) 0.150(4) Uani 0.3333 1 d . U P . .


_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
Cu1 O1 1.9889(10) . ?
Cu1 N2 1.942(2) 15_465 ?
Cu1 N3 1.956(2) 18_556 ?
Cu1 N1 1.998(3) . ?
N2 N3 1.321(3) . ?
N2 C7 1.328(4) . ?
N3 C8 1.344(3) . ?
N1 C5 1.346(5) . ?
N1 C1 1.381(5) . ?
C6 C3 1.452(4) . ?
C6 C7 1.347(4) . ?
C6 C8 1.381(4) . ?
C3 C4 1.408(4) . ?
C3 C2 1.402(5) . ?
C4 H 0.9300 . ?
C4 C5 1.346(4) . ?
C7 HA 0.9300 . ?
C5 HB 0.9300 . ?
N4 O2 1.245(10) 8_656 ?
N4 O2 1.245(10) 11_466 ?
N4 O2 1.245(10) . ?
C8 HC 0.9300 . ?
C1 HD 0.9300 . ?
C1 C2 1.315(5) . ?
C2 HE 0.9300 . ?

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
O1 Cu1 N1 170.97(13) . . ?
N2 Cu1 O1 88.09(6) 15_465 . ?
N2 Cu1 N3 171.69(13) 15_465 18_556 ?
N2 Cu1 N1 91.90(10) 15_465 . ?
N3 Cu1 O1 88.92(7) 18_556 . ?
N3 Cu1 N1 92.26(10) 18_556 . ?
Cu1 O1 Cu1 110.89(8) 8_656 11_466 ?
Cu1 O1 Cu1 110.89(8) 11_466 . ?
Cu1 O1 Cu1 110.90(8) 8_656 . ?
N3 N2 Cu1 120.81(17) . 40_545 ?
N3 N2 C7 107.1(2) . . ?
C7 N2 Cu1 132.1(2) . 40_545 ?
N2 N3 Cu1 119.27(17) . 43_553 ?
N2 N3 C8 109.1(2) . . ?
C8 N3 Cu1 131.5(2) . 43_553 ?
C5 N1 Cu1 123.3(3) . . ?
C5 N1 C1 116.7(3) . . ?
C1 N1 Cu1 119.8(2) . . ?
C7 C6 C3 131.2(3) . . ?
C7 C6 C8 104.1(2) . . ?
C8 C6 C3 124.8(3) . . ?
C4 C3 C6 123.0(3) . . ?
C2 C3 C6 123.5(3) . . ?
C2 C3 C4 113.5(3) . . ?
C3 C4 H 119.8 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H 119.8 . . ?
N2 C7 C6 111.5(3) . . ?
N2 C7 HA 124.3 . . ?
C6 C7 HA 124.3 . . ?
N1 C5 C4 123.9(4) . . ?
N1 C5 HB 118.0 . . ?
C4 C5 HB 118.0 . . ?
O2 N4 O2 75.2(10) . 8_656 ?
O2 N4 O2 75.2(10) 11_466 8_656 ?
O2 N4 O2 75.2(10) 11_466 . ?
N3 C8 C6 108.2(3) . . ?
N3 C8 HC 125.9 . . ?
C6 C8 HC 125.9 . . ?
N1 C1 HD 119.7 . . ?
C2 C1 N1 120.5(3) . . ?
C2 C1 HD 119.7 . . ?
C3 C2 HE 117.8 . . ?
C1 C2 C3 124.4(4) . . ?
C1 C2 HE 117.8 . . ?

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
Cu1 N2 N3 Cu1 5.3(3) 40_545 . . 43_553 ?
Cu1 N2 N3 C8 -178.2(2) 40_545 . . . ?
Cu1 N2 C7 C6 178.9(3) 40_545 . . . ?
Cu1 N3 C8 C6 175.2(3) 43_553 . . . ?
Cu1 N1 C5 C4 -172.2(2) . . . . ?
Cu1 N1 C1 C2 175.2(3) . . . . ?
N2 N3 C8 C6 -0.7(4) . . . . ?
N3 N2 C7 C6 1.3(4) . . . . ?
N1 C1 C2 C3 -6.6(7) . . . . ?
C6 C3 C4 C5 174.0(3) . . . . ?
C6 C3 C2 C1 -170.9(4) . . . . ?
C3 C6 C7 N2 176.7(4) . . . . ?
C3 C6 C8 N3 -177.1(3) . . . . ?
C3 C4 C5 N1 0.7(5) . . . . ?
C4 C3 C2 C1 9.1(6) . . . . ?
C7 N2 N3 Cu1 -176.8(2) . . . 43_553 ?
C7 N2 N3 C8 -0.4(4) . . . . ?
C7 C6 C3 C4 162.0(4) . . . . ?
C7 C6 C3 C2 -17.9(6) . . . . ?
C7 C6 C8 N3 1.4(4) . . . . ?
C5 N1 C1 C2 0.5(5) . . . . ?
C8 C6 C3 C4 -19.9(6) . . . . ?
C8 C6 C3 C2 160.1(4) . . . . ?
C8 C6 C7 N2 -1.7(4) . . . . ?
C1 N1 C5 C4 2.4(5) . . . . ?
C2 C3 C4 C5 -6.0(5) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 3940 electrons were 
found in a volume of 16271Å³ in 1 void per unit cell. 
This is consistent with the presence of 
24[H2O], 0.99[C3H7NO], 1.98[C4H9NO] per Asymmetric Unit 
which account for 5994 electrons 
per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.916 -0.485 -0.397 16271.2 3939.8 '384 H2O,15.84 C3H7NO,31.68 C4H9NO'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.206
_oxdiff_exptl_absorpt_empirical_full_min 0.867
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.87(4)
2 0.13(4)

