# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_a_sq
_database_code_depnum_ccdc_archive 'CCDC 2018785'
loop_
_audit_author_name
_audit_author_address
'Xiaolong Luo'
;CCUT
China
;
_audit_update_record             
;
2020-07-29 deposited with the CCDC.	2023-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H14 Cu N O5'
_chemical_formula_weight         447.89

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c a'
_space_group_name_Hall           '-C 2bc 2'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'x+1/2, -y, z-1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   26.4044(8)
_cell_length_b                   35.6894(11)
_cell_length_c                   17.4068(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     16403.4(9)
_cell_formula_units_Z            16
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    8130
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      23.94

_exptl_crystal_description       Block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.725
_exptl_crystal_F_000             3648
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.550
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51994
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.141
_diffrn_reflns_theta_max         25.103
_diffrn_reflns_theta_full        25.103
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7469
_reflns_number_gt                4837
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1131P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7469
_refine_ls_number_parameters     299
_refine_ls_number_restraints     73
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1758
_refine_ls_wR_factor_gt          0.1452
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.30475(14) 0.30800(8) 1.01359(18) 0.0551(8) Uani 1 1 d . . . . .
C2 C 0.33528(13) 0.34264(9) 1.02507(19) 0.0613(8) Uani 1 1 d . . . . .
C3 C 0.38256(15) 0.34655(9) 0.9908(2) 0.0736(10) Uani 1 1 d . . . . .
H3 H 0.3953 0.3277 0.9594 0.088 Uiso 1 1 calc R U . . .
C4 C 0.41046(14) 0.37857(10) 1.0036(2) 0.0752(10) Uani 1 1 d . . . . .
H4 H 0.4420 0.3810 0.9803 0.090 Uiso 1 1 calc R U . . .
C5 C 0.39311(15) 0.40665(10) 1.0494(2) 0.0722(10) Uani 1 1 d . . . . .
C6 C 0.34648(17) 0.40285(11) 1.0835(3) 0.1049(16) Uani 1 1 d . . . . .
H6 H 0.3341 0.4217 1.1152 0.126 Uiso 1 1 calc R U . . .
C7 C 0.31778(16) 0.37100(10) 1.0708(3) 0.0932(14) Uani 1 1 d . . . . .
H7 H 0.2861 0.3688 1.0937 0.112 Uiso 1 1 calc R U . . .
C8 C 0.42188(15) 0.43983(10) 1.0653(2) 0.0761(10) Uani 1 1 d . . . . .
C9 C 0.44581(14) 0.46676(9) 1.0803(2) 0.0709(10) Uani 1 1 d . . . . .
C10 C 0.47318(10) 0.49993(8) 1.10293(18) 0.0565(8) Uani 1 1 d . . . . .
C11 C 0.44826(12) 0.53144(8) 1.1280(2) 0.0655(9) Uani 1 1 d . . . . .
H11 H 0.4131 0.5318 1.1265 0.079 Uiso 1 1 calc R U . . .
C12 C 0.47333(10) 0.56252(8) 1.15526(18) 0.0567(8) Uani 1 1 d . . . . .
C13 C 0.44602(13) 0.59365(9) 1.1875(2) 0.0675(9) Uani 1 1 d . . . . .
C14 C 0.42293(14) 0.61732(10) 1.2178(2) 0.0760(10) Uani 1 1 d . . . . .
C15 C 0.39527(15) 0.64465(10) 1.2626(2) 0.0782(11) Uani 1 1 d . . . . .
C16 C 0.40835(18) 0.64983(13) 1.3375(3) 0.1179(17) Uani 1 1 d . . . . .
H16 H 0.4364 0.6374 1.3574 0.142 Uiso 1 1 calc R U . . .
C17 C 0.38017(17) 0.67360(13) 1.3845(3) 0.1143(17) Uani 1 1 d . . . . .
H17 H 0.3897 0.6771 1.4355 0.137 Uiso 1 1 calc R U . . .
C18 C 0.33857(13) 0.69172(9) 1.3559(2) 0.0668(9) Uani 1 1 d . . . . .
C19 C 0.32706(14) 0.68793(11) 1.2794(2) 0.0813(11) Uani 1 1 d . . . . .
H19 H 0.3000 0.7012 1.2587 0.098 Uiso 1 1 calc R U . . .
C20 C 0.35497(15) 0.66480(11) 1.2333(2) 0.0913(13) Uani 1 1 d . . . . .
H20 H 0.3467 0.6626 1.1815 0.110 Uiso 1 1 calc R U . . .
C21 C 0.19349(14) 0.28519(9) 0.9087(2) 0.0627(9) Uani 1 1 d . . . . .
C22A C 0.3633(4) 0.2261(5) 0.8362(7) 0.140(3) Uani 0.391(5) 1 d D U P A 1
H22A H 0.3796 0.2397 0.8744 0.168 Uiso 0.391(5) 1 calc R U P A 1
C23A C 0.3687(7) 0.2077(5) 0.7032(7) 0.134(5) Uani 0.391(5) 1 d D U P A 1
H23A H 0.3394 0.1919 0.7076 0.200 Uiso 0.391(5) 1 d R U P A 1
H23B H 0.3922 0.1968 0.6675 0.200 Uiso 0.391(5) 1 d R U P A 1
H23C H 0.3586 0.2320 0.6853 0.200 Uiso 0.391(5) 1 d R U P A 1
N1A N 0.3922(4) 0.2140(4) 0.7737(7) 0.169(4) Uani 0.391(5) 1 d D U P A 1
H1A H 0.4242 0.2104 0.7788 0.203 Uiso 0.391(5) 1 calc R U P A 1
C22B C 0.2985(3) 0.2158(2) 0.7843(4) 0.102(2) Uani 0.609(5) 1 d D U P A 2
H22B H 0.2644 0.2222 0.7824 0.122 Uiso 0.609(5) 1 calc R U P A 2
C23B C 0.3686(5) 0.1848(4) 0.7234(7) 0.181(5) Uani 0.609(5) 1 d D U P A 2
H23D H 0.3746 0.1740 0.7730 0.272 Uiso 0.609(5) 1 d R U P A 2
H23E H 0.3929 0.2043 0.7141 0.272 Uiso 0.609(5) 1 d R U P A 2
H23F H 0.3719 0.1659 0.6846 0.272 Uiso 0.609(5) 1 d R U P A 2
N1B N 0.3191(3) 0.2024(2) 0.7189(4) 0.132(2) Uani 0.609(5) 1 d D U P A 2
H1B H 0.3034 0.2042 0.6758 0.159 Uiso 0.609(5) 1 calc R U P A 2
Cu1 Cu 0.27889(2) 0.23999(2) 0.94172(2) 0.05014(16) Uani 1 1 d D . . . .
O1 O 0.23066(9) 0.26846(6) 0.87917(14) 0.0686(6) Uani 1 1 d . . . . .
O2 O 0.31886(9) 0.21496(7) 1.02127(14) 0.0732(7) Uani 1 1 d . . . . .
O3 O 0.23193(10) 0.19710(6) 0.94052(13) 0.0691(7) Uani 1 1 d . . . . .
O4 O 0.31734(9) 0.28618(6) 0.96035(13) 0.0660(6) Uani 1 1 d . . . . .
O5 O 0.31935(9) 0.22028(8) 0.84411(14) 0.0778(7) Uani 1 1 d D U . . .


_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 O3 1.269(4) 13_557 ?
C1 O4 1.255(4) . ?
C1 C2 1.489(4) . ?
C2 C7 1.368(5) . ?
C2 C3 1.391(5) . ?
C3 C4 1.378(4) . ?
C4 C5 1.361(5) . ?
C5 C6 1.373(5) . ?
C5 C8 1.434(5) . ?
C6 C7 1.384(5) . ?
C8 C9 1.179(4) . ?
C9 C10 1.442(4) . ?
C10 C11 1.374(4) . ?
C10 C10 1.416(6) 12_655 ?
C11 C12 1.376(4) . ?
C12 C12 1.409(6) 12_655 ?
C12 C13 1.439(4) . ?
C13 C14 1.168(4) . ?
C14 C15 1.447(4) . ?
C15 C16 1.361(6) . ?
C15 C20 1.382(5) . ?
C16 C17 1.394(5) . ?
C17 C18 1.368(5) . ?
C18 C19 1.373(5) . ?
C18 C21 1.497(4) 6 ?
C19 C20 1.367(5) . ?
C21 O2 1.261(4) 13_557 ?
C21 O1 1.259(4) . ?
C21 C18 1.497(4) 6_554 ?
C22A O5 1.186(10) . ?
C22A N1A 1.398(10) . ?
C23A N1A 1.394(14) . ?
C22B O5 1.188(7) . ?
C22B N1B 1.351(8) . ?
C23B N1B 1.450(11) . ?
Cu1 O2 1.957(2) . ?
Cu1 O4 1.963(2) . ?
Cu1 O1 1.960(2) . ?
Cu1 O3 1.970(2) . ?
Cu1 O5 2.127(3) . ?
Cu1 Cu1 2.6372(8) 13_557 ?
O2 C21 1.261(4) 13_557 ?
O3 C1 1.269(4) 13_557 ?

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
O3 C1 O4 125.3(3) 13_557 . ?
O3 C1 C2 116.6(3) 13_557 . ?
O4 C1 C2 118.1(3) . . ?
C7 C2 C3 118.6(3) . . ?
C7 C2 C1 120.6(3) . . ?
C3 C2 C1 120.8(3) . . ?
C2 C3 C4 119.6(3) . . ?
C5 C4 C3 121.7(4) . . ?
C4 C5 C6 118.8(3) . . ?
C4 C5 C8 122.9(4) . . ?
C6 C5 C8 118.3(3) . . ?
C7 C6 C5 120.2(4) . . ?
C2 C7 C6 121.1(4) . . ?
C9 C8 C5 178.2(4) . . ?
C8 C9 C10 176.5(4) . . ?
C11 C10 C10 118.61(17) . 12_655 ?
C11 C10 C9 121.2(3) . . ?
C10 C10 C9 120.08(18) 12_655 . ?
C10 C11 C12 122.6(3) . . ?
C11 C12 C12 118.75(17) . 12_655 ?
C11 C12 C13 121.1(3) . . ?
C12 C12 C13 120.08(17) 12_655 . ?
C14 C13 C12 175.4(4) . . ?
C13 C14 C15 174.2(4) . . ?
C16 C15 C20 118.6(3) . . ?
C16 C15 C14 118.6(4) . . ?
C20 C15 C14 122.7(4) . . ?
C15 C16 C17 120.6(4) . . ?
C18 C17 C16 120.1(4) . . ?
C17 C18 C19 119.0(3) . . ?
C17 C18 C21 119.4(4) . 6 ?
C19 C18 C21 121.7(3) . 6 ?
C20 C19 C18 120.7(4) . . ?
C19 C20 C15 120.8(4) . . ?
O2 C21 O1 126.5(3) 13_557 . ?
O2 C21 C18 116.7(3) 13_557 6_554 ?
O1 C21 C18 116.8(3) . 6_554 ?
O5 C22A N1A 124.8(11) . . ?
C22A N1A C23A 119.4(10) . . ?
O5 C22B N1B 126.8(7) . . ?
C22B N1B C23B 118.1(7) . . ?
O2 Cu1 O4 89.29(10) . . ?
O2 Cu1 O1 168.64(11) . . ?
O4 Cu1 O1 89.57(9) . . ?
O2 Cu1 O3 89.55(10) . . ?
O4 Cu1 O3 168.46(10) . . ?
O1 Cu1 O3 89.31(10) . . ?
O2 Cu1 O5 98.25(10) . . ?
O4 Cu1 O5 98.63(10) . . ?
O1 Cu1 O5 93.10(10) . . ?
O3 Cu1 O5 92.90(10) . . ?
O2 Cu1 Cu1 83.76(8) . 13_557 ?
O4 Cu1 Cu1 86.83(7) . 13_557 ?
O1 Cu1 Cu1 84.89(8) . 13_557 ?
O3 Cu1 Cu1 81.63(7) . 13_557 ?
O5 Cu1 Cu1 174.18(7) . 13_557 ?
C21 O1 Cu1 121.7(2) . . ?
C21 O2 Cu1 123.1(2) 13_557 . ?
C1 O3 Cu1 125.8(2) 13_557 . ?
C1 O4 Cu1 120.4(2) . . ?
C22A O5 Cu1 121.7(6) . . ?
C22B O5 Cu1 120.8(4) . . ?

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
O3 C1 C2 C7 -14.1(5) 13_557 . . . ?
O4 C1 C2 C7 166.5(4) . . . . ?
O3 C1 C2 C3 164.6(3) 13_557 . . . ?
O4 C1 C2 C3 -14.8(5) . . . . ?
C7 C2 C3 C4 0.1(6) . . . . ?
C1 C2 C3 C4 -178.7(3) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C3 C4 C5 C6 -0.1(6) . . . . ?
C3 C4 C5 C8 178.4(4) . . . . ?
C4 C5 C6 C7 -0.4(7) . . . . ?
C8 C5 C6 C7 -179.0(4) . . . . ?
C3 C2 C7 C6 -0.6(6) . . . . ?
C1 C2 C7 C6 178.2(4) . . . . ?
C5 C6 C7 C2 0.7(7) . . . . ?
C10 C10 C11 C12 -2.0(4) 12_655 . . . ?
C9 C10 C11 C12 175.1(3) . . . . ?
C10 C11 C12 C12 2.0(4) . . . 12_655 ?
C10 C11 C12 C13 -174.3(3) . . . . ?
C20 C15 C16 C17 3.0(8) . . . . ?
C14 C15 C16 C17 -174.7(4) . . . . ?
C15 C16 C17 C18 0.7(8) . . . . ?
C16 C17 C18 C19 -4.0(7) . . . . ?
C16 C17 C18 C21 175.4(4) . . . 6 ?
C17 C18 C19 C20 3.6(6) . . . . ?
C21 C18 C19 C20 -175.8(4) 6 . . . ?
C18 C19 C20 C15 0.2(7) . . . . ?
C16 C15 C20 C19 -3.5(7) . . . . ?
C14 C15 C20 C19 174.2(4) . . . . ?
O5 C22A N1A C23A 26(3) . . . . ?
O5 C22B N1B C23B 12.7(16) . . . . ?
O2 C21 O1 Cu1 -2.8(5) 13_557 . . . ?
C18 C21 O1 Cu1 175.7(2) 6_554 . . . ?
O3 C1 O4 Cu1 0.7(4) 13_557 . . . ?
C2 C1 O4 Cu1 -180.0(2) . . . . ?
N1A C22A O5 Cu1 179.9(12) . . . . ?
N1B C22B O5 Cu1 -177.7(7) . . . . ?

_refine_diff_density_max         0.484
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.055



