# Supplementary Information (SI) for ChemComm.
# 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_ydkr
_database_code_depnum_ccdc_archive 'CCDC 2321776'
loop_
_audit_author_name
_audit_author_address
'XIN ZHENG'
;Hokkaido University
Japan
;
_audit_update_record             
;
2023-12-26 deposited with the CCDC.	2024-08-13 downloaded from the CCDC.
;
_audit_creation_date             2023-12-26
_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 H24 Cu N4, 2(C2 F6 N O4 S2)'
_chemical_formula_sum            'C28 H24 Cu F12 N6 O8 S4'
_chemical_formula_weight         992.31
_chemical_absolute_configuration unk
_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'
F F 0.0727 0.0534 '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'
S S 0.3331 0.5567 '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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   19.966(6)
_cell_length_b                   9.159(2)
_cell_length_c                   11.301(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.602(9)
_cell_angle_gamma                90
_cell_volume                     1958.6(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1263
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      149.016
_cell_measurement_theta_min      43.331
_shelx_estimated_absorpt_T_max   0.516
_shelx_estimated_absorpt_T_min   0.516
_exptl_absorpt_coefficient_mu    3.812
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             998
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7180
_diffrn_reflns_point_group_measured_fraction_full 0.896
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         75.366
_diffrn_reflns_theta_min         7.166
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_radiation_wavelength     1.54187
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    0.808
_reflns_Friedel_fraction_max     0.742
_reflns_number_gt                3018
_reflns_number_total             3438
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 1134 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.030(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3438
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0278
_refine_ls_restrained_S_all      0.945
_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)+(0.0312P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0592
_refine_ls_wR_factor_ref         0.0602
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C4(H4), C1(H1), C10(H10), C9(H9), C12(H12), C5(H5), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.500000 0.82740(7) 0.500000 0.02846(18) Uani 1 2 d S T P . .
S002 S 0.62286(4) 0.48797(9) 0.20481(8) 0.0316(2) Uani 1 1 d . . . . .
S003 S 0.63382(4) 0.76764(9) 0.30876(8) 0.03039(19) Uani 1 1 d . . . . .
F5 F 0.53148(12) 0.8950(3) 0.1330(2) 0.0563(7) Uani 1 1 d . . . . .
F4 F 0.61927(12) 0.8304(3) 0.07379(19) 0.0528(6) Uani 1 1 d . . . . .
F3 F 0.72416(13) 0.4587(3) 0.4188(2) 0.0540(6) Uani 1 1 d . . . . .
O3 O 0.70840(12) 0.7690(3) 0.3371(2) 0.0382(6) Uani 1 1 d . . . . .
O1 O 0.56532(14) 0.3960(3) 0.1431(3) 0.0469(7) Uani 1 1 d . . . . .
F1 F 0.63638(14) 0.3148(3) 0.3956(2) 0.0581(6) Uani 1 1 d . . . . .
O2 O 0.67056(13) 0.5308(3) 0.1407(2) 0.0369(6) Uani 1 1 d . . . . .
F2 F 0.71033(14) 0.2750(3) 0.2959(3) 0.0661(7) Uani 1 1 d . . . . .
O4 O 0.60356(13) 0.8348(3) 0.3946(2) 0.0378(5) Uani 1 1 d . . . . .
F6 F 0.62844(17) 1.0155(3) 0.1943(3) 0.0706(8) Uani 1 1 d . . . . .
N2 N 0.44355(15) 0.6752(3) 0.3812(3) 0.0276(6) Uani 1 1 d . . . . .
N1 N 0.44867(14) -0.0165(3) 0.3812(3) 0.0280(6) Uani 1 1 d . . . . .
N3 N 0.59457(14) 0.6167(3) 0.2694(3) 0.0306(6) Uani 1 1 d . . . . .
C8 C 0.34901(17) 0.4897(4) 0.2106(3) 0.0260(7) Uani 1 1 d . . . . .
C3 C 0.37866(18) 0.1688(3) 0.1838(3) 0.0278(7) Uani 1 1 d . . . . .
C11 C 0.43316(19) 0.6847(4) 0.2583(3) 0.0318(8) Uani 1 1 d . . . . .
H11 H 0.458366 0.757046 0.229460 0.038 Uiso 1 1 calc R U . . .
C4 C 0.45141(19) 0.1707(4) 0.2354(3) 0.0315(8) Uani 1 1 d . . . . .
H4 H 0.478674 0.235535 0.203614 0.038 Uiso 1 1 calc R U . . .
C1 C 0.37782(17) -0.0154(4) 0.3335(3) 0.0310(7) Uani 1 1 d . . . . .
H1 H 0.351573 -0.080088 0.367501 0.037 Uiso 1 1 calc R U . . .
C10 C 0.40743(19) 0.5703(4) 0.4197(3) 0.0302(8) Uani 1 1 d . . . . .
H10 H 0.415109 0.559310 0.506573 0.036 Uiso 1 1 calc R U . . .
C9 C 0.36011(18) 0.4791(4) 0.3379(3) 0.0317(7) Uani 1 1 d . . . . .
H9 H 0.334908 0.408589 0.368597 0.038 Uiso 1 1 calc R U . . .
C12 C 0.38788(18) 0.5949(4) 0.1721(3) 0.0317(8) Uani 1 1 d . . . . .
H12 H 0.383054 0.604535 0.086105 0.038 Uiso 1 1 calc R U . . .
C5 C 0.48437(18) 0.0786(4) 0.3331(3) 0.0305(8) Uani 1 1 d . . . . .
H5 H 0.534387 0.082437 0.367896 0.037 Uiso 1 1 calc R U . . .
C2 C 0.34180(19) 0.0751(4) 0.2378(4) 0.0336(8) Uani 1 1 d . . . . .
H2 H 0.291602 0.073983 0.208353 0.040 Uiso 1 1 calc R U . . .
C6 C 0.34047(19) 0.2665(4) 0.0763(3) 0.0345(8) Uani 1 1 d . . . . .
H6A H 0.306909 0.207387 0.010274 0.041 Uiso 1 1 calc R U . . .
H6B H 0.375105 0.310431 0.040694 0.041 Uiso 1 1 calc R U . . .
C14 C 0.6011(2) 0.8829(4) 0.1690(4) 0.0423(9) Uani 1 1 d . . . . .
C7 C 0.29969(19) 0.3893(4) 0.1176(3) 0.0319(8) Uani 1 1 d . . . . .
H7A H 0.272260 0.446243 0.043502 0.038 Uiso 1 1 calc R U . . .
H7B H 0.265933 0.345464 0.155271 0.038 Uiso 1 1 calc R U . . .
C13 C 0.6763(2) 0.3796(4) 0.3369(4) 0.0414(9) Uani 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
Cu1 N2 2.012(3) . ?
Cu1 N2 2.012(3) 2_656 ?
Cu1 N1 2.004(3) 2_666 ?
Cu1 N1 2.004(3) 1_565 ?
S002 O1 1.416(3) . ?
S002 O2 1.423(3) . ?
S002 N3 1.582(3) . ?
S002 C13 1.827(4) . ?
S003 O3 1.420(2) . ?
S003 O4 1.435(2) . ?
S003 N3 1.582(3) . ?
S003 C14 1.838(4) . ?
F5 C14 1.322(5) . ?
F4 C14 1.330(5) . ?
F3 C13 1.315(5) . ?
F1 C13 1.328(5) . ?
F2 C13 1.340(4) . ?
F6 C14 1.325(5) . ?
N2 C11 1.341(5) . ?
N2 C10 1.353(4) . ?
N1 C1 1.344(4) . ?
N1 C5 1.346(5) . ?
C8 C9 1.387(5) . ?
C8 C12 1.391(5) . ?
C8 C7 1.504(5) . ?
C3 C4 1.382(5) . ?
C3 C2 1.392(5) . ?
C3 C6 1.506(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.371(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.370(5) . ?
C10 H10 0.9500 . ?
C10 C9 1.374(5) . ?
C9 H9 0.9500 . ?
C12 H12 0.9500 . ?
C5 H5 0.9500 . ?
C2 H2 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.545(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

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
N2 Cu1 N2 92.33(17) . 2_656 ?
N1 Cu1 N2 89.39(10) 2_666 2_656 ?
N1 Cu1 N2 176.92(13) 2_666 . ?
N1 Cu1 N2 89.39(10) 1_565 . ?
N1 Cu1 N2 176.92(13) 1_565 2_656 ?
N1 Cu1 N1 89.01(17) 2_666 1_565 ?
O1 S002 O2 118.89(16) . . ?
O1 S002 N3 108.49(16) . . ?
O1 S002 C13 104.47(19) . . ?
O2 S002 N3 115.11(15) . . ?
O2 S002 C13 104.76(17) . . ?
N3 S002 C13 103.26(17) . . ?
O3 S003 O4 118.77(15) . . ?
O3 S003 N3 117.45(16) . . ?
O3 S003 C14 104.42(17) . . ?
O4 S003 N3 106.71(16) . . ?
O4 S003 C14 102.92(17) . . ?
N3 S003 C14 104.56(17) . . ?
C11 N2 Cu1 121.0(2) . . ?
C11 N2 C10 117.2(3) . . ?
C10 N2 Cu1 121.3(2) . . ?
C1 N1 Cu1 121.5(2) . 1_545 ?
C1 N1 C5 117.3(3) . . ?
C5 N1 Cu1 120.6(2) . 1_545 ?
S003 N3 S002 124.29(18) . . ?
C9 C8 C12 116.9(3) . . ?
C9 C8 C7 122.3(3) . . ?
C12 C8 C7 120.8(3) . . ?
C4 C3 C2 117.1(3) . . ?
C4 C3 C6 121.8(3) . . ?
C2 C3 C6 121.2(3) . . ?
N2 C11 H11 118.5 . . ?
N2 C11 C12 123.1(3) . . ?
C12 C11 H11 118.5 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.0 . . ?
N1 C1 H1 118.6 . . ?
N1 C1 C2 122.8(3) . . ?
C2 C1 H1 118.6 . . ?
N2 C10 H10 118.7 . . ?
N2 C10 C9 122.6(3) . . ?
C9 C10 H10 118.7 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C12 H12 120.0 . . ?
C11 C12 C8 120.1(3) . . ?
C11 C12 H12 120.0 . . ?
N1 C5 C4 122.7(3) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 C3 120.1(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C6 H6A 109.3 . . ?
C3 C6 H6B 109.3 . . ?
C3 C6 C7 111.7(3) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
F5 C14 S003 111.4(3) . . ?
F5 C14 F4 108.3(3) . . ?
F5 C14 F6 108.0(3) . . ?
F4 C14 S003 111.9(3) . . ?
F6 C14 S003 109.4(3) . . ?
F6 C14 F4 107.8(4) . . ?
C8 C7 C6 111.4(3) . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
F3 C13 S002 112.3(3) . . ?
F3 C13 F1 108.2(3) . . ?
F3 C13 F2 107.6(3) . . ?
F1 C13 S002 111.3(3) . . ?
F1 C13 F2 107.7(3) . . ?
F2 C13 S002 109.5(3) . . ?

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 C11 C12 -171.4(3) . . . . ?
Cu1 N2 C10 C9 169.8(3) . . . . ?
Cu1 N1 C1 C2 -169.4(3) 1_545 . . . ?
Cu1 N1 C5 C4 168.3(3) 1_545 . . . ?
O3 S003 N3 S002 -27.2(3) . . . . ?
O3 S003 C14 F5 -178.4(3) . . . . ?
O3 S003 C14 F4 60.3(3) . . . . ?
O3 S003 C14 F6 -59.0(3) . . . . ?
O1 S002 N3 S003 -159.0(2) . . . . ?
O1 S002 C13 F3 -166.9(3) . . . . ?
O1 S002 C13 F1 -45.4(3) . . . . ?
O1 S002 C13 F2 73.6(3) . . . . ?
O2 S002 N3 S003 -23.0(3) . . . . ?
O2 S002 C13 F3 67.3(3) . . . . ?
O2 S002 C13 F1 -171.2(3) . . . . ?
O2 S002 C13 F2 -52.1(3) . . . . ?
O4 S003 N3 S002 -163.4(2) . . . . ?
O4 S003 C14 F5 -53.7(3) . . . . ?
O4 S003 C14 F4 -175.0(3) . . . . ?
O4 S003 C14 F6 65.6(3) . . . . ?
N2 C11 C12 C8 1.3(5) . . . . ?
N2 C10 C9 C8 1.7(5) . . . . ?
N1 C1 C2 C3 1.6(6) . . . . ?
N3 S002 C13 F3 -53.5(3) . . . . ?
N3 S002 C13 F1 68.0(3) . . . . ?
N3 S002 C13 F2 -173.0(3) . . . . ?
N3 S003 C14 F5 57.7(3) . . . . ?
N3 S003 C14 F4 -63.7(3) . . . . ?
N3 S003 C14 F6 177.0(3) . . . . ?
C3 C4 C5 N1 0.7(5) . . . . ?
C3 C6 C7 C8 63.5(4) . . . . ?
C11 N2 C10 C9 -2.1(5) . . . . ?
C4 C3 C2 C1 -3.4(5) . . . . ?
C4 C3 C6 C7 -108.7(4) . . . . ?
C1 N1 C5 C4 -2.6(5) . . . . ?
C10 N2 C11 C12 0.6(5) . . . . ?
C9 C8 C12 C11 -1.7(5) . . . . ?
C9 C8 C7 C6 -100.3(4) . . . . ?
C12 C8 C9 C10 0.3(5) . . . . ?
C12 C8 C7 C6 77.2(4) . . . . ?
C5 N1 C1 C2 1.5(5) . . . . ?
C2 C3 C4 C5 2.3(5) . . . . ?
C2 C3 C6 C7 69.5(4) . . . . ?
C6 C3 C4 C5 -179.5(3) . . . . ?
C6 C3 C2 C1 178.4(3) . . . . ?
C14 S003 N3 S002 88.0(2) . . . . ?
C7 C8 C9 C10 177.9(3) . . . . ?
C7 C8 C12 C11 -179.4(3) . . . . ?
C13 S002 N3 S003 90.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
