# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_SPA766
_database_code_depnum_ccdc_archive 'CCDC 2240777'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2023-02-09 deposited with the CCDC.	2023-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H14 Cu N2 O6'
_chemical_formula_sum            'C11 H14 Cu N2 O6'
_chemical_formula_weight         333.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3383 1.0252 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   5.0850(10)
_cell_length_b                   11.293(2)
_cell_length_c                   11.036(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.76(3)
_cell_angle_gamma                90
_cell_volume                     633.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    19842
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_F_000             342
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.062
_exptl_crystal_size_mid          0.028
_exptl_crystal_size_min          0.019
_exptl_absorpt_coefficient_mu    1.264
_shelx_estimated_absorpt_T_min   0.926
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6943
_diffrn_reflns_av_unetI/netI     0.1001
_diffrn_reflns_av_R_equivalents  0.1130
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.638
_diffrn_reflns_theta_max         26.489
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3770
_reflns_number_gt                3263
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.910
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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.
;

_computing_data_collection       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_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)+(0.1067P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1236 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(12)
_chemical_absolute_configuration .
_refine_ls_number_reflns         3770
_refine_ls_number_parameters     187
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.1746
_refine_ls_wR_factor_gt          0.1704
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.063
_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
Cu1 Cu 0.56496(11) 0.49397(8) 0.73950(5) 0.0225(2) Uani 1 1 d . . . . .
O1 O 0.8865(8) 0.5173(4) 0.8533(4) 0.0250(9) Uani 1 1 d . . . . .
O2 O 1.2281(10) 0.4163(6) 0.9345(5) 0.0368(11) Uani 1 1 d . . . . .
O3 O 0.2768(9) 0.4144(4) 0.6335(4) 0.0256(9) Uani 1 1 d . . . . .
O4 O 0.1573(10) 0.2376(5) 0.5601(4) 0.0324(10) Uani 1 1 d . . . . .
O5 O 0.8098(9) 0.5342(5) 0.5775(5) 0.0325(11) Uani 1 1 d D . . . .
H1O5 H 0.798(17) 0.585(6) 0.513(5) 0.049 Uiso 1 1 d D U . . .
H2O5 H 0.955(13) 0.487(8) 0.585(7) 0.049 Uiso 1 1 d D U . . .
O6 O 0.3006(11) 0.8949(5) 0.7690(5) 0.0355(11) Uani 1 1 d . . . . .
N1 N 0.6779(10) 0.3335(5) 0.7535(4) 0.0208(9) Uani 1 1 d . . . . .
N2 N 0.3716(10) 0.6432(5) 0.7594(4) 0.0212(9) Uani 1 1 d . . . . .
H2 H 0.187672 0.620478 0.773791 0.025 Uiso 1 1 calc R U . . .
C1 C 1.0123(12) 0.4227(7) 0.8788(5) 0.0245(12) Uani 1 1 d . . . . .
C2 C 0.8853(11) 0.3101(6) 0.8287(5) 0.0233(11) Uani 1 1 d . . . . .
C3 C 0.9539(14) 0.1926(7) 0.8513(6) 0.0323(14) Uani 1 1 d . . . . .
H3 H 1.098187 0.173650 0.904176 0.039 Uiso 1 1 calc R U . . .
C4 C 0.8057(15) 0.1043(7) 0.7945(7) 0.0380(16) Uani 1 1 d . . . . .
H4 H 0.848657 0.024544 0.809676 0.046 Uiso 1 1 calc R U . . .
C5 C 0.5944(13) 0.1318(7) 0.7152(7) 0.0306(13) Uani 1 1 d . . . . .
H5 H 0.495209 0.071813 0.675635 0.037 Uiso 1 1 calc R U . . .
C6 C 0.5335(13) 0.2502(6) 0.6960(6) 0.0248(11) Uani 1 1 d . . . . .
C7 C 0.3041(12) 0.3009(6) 0.6225(6) 0.0223(11) Uani 1 1 d . . . . .
C8 C 0.3589(15) 0.7186(6) 0.6492(5) 0.0250(12) Uani 1 1 d . . . . .
H8A H 0.281006 0.673292 0.580780 0.030 Uiso 1 1 calc R U . . .
H8B H 0.537620 0.741491 0.629221 0.030 Uiso 1 1 calc R U . . .
C9 C 0.1966(15) 0.8288(6) 0.6679(6) 0.0339(14) Uani 1 1 d . . . . .
H9A H 0.196157 0.878070 0.594812 0.041 Uiso 1 1 calc R U . . .
H9B H 0.014292 0.806285 0.681669 0.041 Uiso 1 1 calc R U . . .
C10 C 0.3010(13) 0.8258(6) 0.8766(6) 0.0305(13) Uani 1 1 d . . . . .
H10A H 0.119564 0.804025 0.893082 0.037 Uiso 1 1 calc R U . . .
H10B H 0.371779 0.873158 0.945013 0.037 Uiso 1 1 calc R U . . .
C11 C 0.4635(13) 0.7147(6) 0.8663(6) 0.0271(12) Uani 1 1 d . . . . .
H11A H 0.648672 0.736188 0.858652 0.032 Uiso 1 1 calc R U . . .
H11B H 0.450668 0.667309 0.940168 0.032 Uiso 1 1 calc R 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
Cu1 N1 1.905(5) . ?
Cu1 N2 1.969(5) . ?
Cu1 O1 2.030(5) . ?
Cu1 O3 2.039(5) . ?
Cu1 O5 2.273(4) . ?
O1 C1 1.270(8) . ?
O2 C1 1.234(7) . ?
O3 C7 1.296(8) . ?
O4 C7 1.222(8) . ?
O5 H1O5 0.914(14) . ?
O5 H2O5 0.914(14) . ?
O6 C10 1.421(9) . ?
O6 C9 1.422(9) . ?
N1 C6 1.335(8) . ?
N1 C2 1.337(7) . ?
N2 C8 1.483(8) . ?
N2 C11 1.486(8) . ?
N2 H2 0.9900 . ?
C1 C2 1.518(10) . ?
C2 C3 1.391(10) . ?
C3 C4 1.382(11) . ?
C3 H3 0.9400 . ?
C4 C5 1.387(9) . ?
C4 H4 0.9400 . ?
C5 C6 1.386(10) . ?
C5 H5 0.9400 . ?
C6 C7 1.502(9) . ?
C8 C9 1.513(10) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 C11 1.509(9) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 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
_geom_angle_publ_flag
N1 Cu1 N2 162.8(2) . . ?
N1 Cu1 O1 80.9(2) . . ?
N2 Cu1 O1 102.2(2) . . ?
N1 Cu1 O3 80.4(2) . . ?
N2 Cu1 O3 95.3(2) . . ?
O1 Cu1 O3 161.28(19) . . ?
N1 Cu1 O5 94.56(19) . . ?
N2 Cu1 O5 102.2(2) . . ?
O1 Cu1 O5 90.31(19) . . ?
O3 Cu1 O5 92.44(19) . . ?
C1 O1 Cu1 114.2(4) . . ?
C7 O3 Cu1 114.3(4) . . ?
Cu1 O5 H1O5 136(5) . . ?
Cu1 O5 H2O5 106(4) . . ?
H1O5 O5 H2O5 117(4) . . ?
C10 O6 C9 110.6(5) . . ?
C6 N1 C2 123.7(6) . . ?
C6 N1 Cu1 118.4(4) . . ?
C2 N1 Cu1 117.7(4) . . ?
C8 N2 C11 109.8(5) . . ?
C8 N2 Cu1 113.7(4) . . ?
C11 N2 Cu1 114.4(4) . . ?
C8 N2 H2 106.1 . . ?
C11 N2 H2 106.1 . . ?
Cu1 N2 H2 106.1 . . ?
O2 C1 O1 125.8(7) . . ?
O2 C1 C2 119.0(6) . . ?
O1 C1 C2 115.0(5) . . ?
N1 C2 C3 118.9(6) . . ?
N1 C2 C1 111.7(5) . . ?
C3 C2 C1 129.4(6) . . ?
C4 C3 C2 118.7(6) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 120.9(7) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.2(7) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
N1 C6 C5 119.6(6) . . ?
N1 C6 C7 112.6(6) . . ?
C5 C6 C7 127.7(6) . . ?
O4 C7 O3 124.5(7) . . ?
O4 C7 C6 121.3(6) . . ?
O3 C7 C6 114.2(6) . . ?
N2 C8 C9 111.3(5) . . ?
N2 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N2 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
O6 C9 C8 110.7(6) . . ?
O6 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
O6 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
O6 C10 C11 111.9(5) . . ?
O6 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
O6 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N2 C11 C10 111.0(5) . . ?
N2 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
N2 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?

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 O1 C1 O2 171.4(5) . . . . ?
Cu1 O1 C1 C2 -5.2(6) . . . . ?
C6 N1 C2 C3 -1.4(9) . . . . ?
Cu1 N1 C2 C3 172.8(5) . . . . ?
C6 N1 C2 C1 179.1(5) . . . . ?
Cu1 N1 C2 C1 -6.7(6) . . . . ?
O2 C1 C2 N1 -169.1(5) . . . . ?
O1 C1 C2 N1 7.8(7) . . . . ?
O2 C1 C2 C3 11.4(10) . . . . ?
O1 C1 C2 C3 -171.7(6) . . . . ?
N1 C2 C3 C4 0.4(10) . . . . ?
C1 C2 C3 C4 179.8(6) . . . . ?
C2 C3 C4 C5 0.8(11) . . . . ?
C3 C4 C5 C6 -0.9(11) . . . . ?
C2 N1 C6 C5 1.2(9) . . . . ?
Cu1 N1 C6 C5 -173.0(5) . . . . ?
C2 N1 C6 C7 176.9(5) . . . . ?
Cu1 N1 C6 C7 2.8(7) . . . . ?
C4 C5 C6 N1 0.0(10) . . . . ?
C4 C5 C6 C7 -175.0(6) . . . . ?
Cu1 O3 C7 O4 -177.7(5) . . . . ?
Cu1 O3 C7 C6 3.5(6) . . . . ?
N1 C6 C7 O4 177.0(5) . . . . ?
C5 C6 C7 O4 -7.7(10) . . . . ?
N1 C6 C7 O3 -4.1(8) . . . . ?
C5 C6 C7 O3 171.2(6) . . . . ?
C11 N2 C8 C9 -53.2(7) . . . . ?
Cu1 N2 C8 C9 177.1(5) . . . . ?
C10 O6 C9 C8 -59.7(7) . . . . ?
N2 C8 C9 O6 57.4(8) . . . . ?
C9 O6 C10 C11 59.4(7) . . . . ?
C8 N2 C11 C10 52.1(6) . . . . ?
Cu1 N2 C11 C10 -178.6(4) . . . . ?
O6 C10 C11 N2 -55.9(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H1O5 O4 0.914(14) 1.92(5) 2.763(7) 152(9) 2_656 yes
O5 H2O5 O3 0.914(14) 1.88(3) 2.776(7) 166(10) 1_655 yes
N2 H2 O1 0.99 2.15 3.070(7) 154.8 1_455 yes
C5 H5 O6 0.94 2.48 3.135(10) 127.2 1_545 yes
C9 H9A O5 0.98 2.59 3.565(9) 171.7 2_656 yes
C10 H10B O2 0.98 2.43 3.263(8) 143.1 2_757 yes

_refine_diff_density_max         2.973
_refine_diff_density_min         -1.038
_refine_diff_density_rms         0.171

