# Electronic Supplementary Material (ESI) for RSC Sustainability.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2177365'
loop_
_audit_author_name
_audit_author_address
'Vania Andre'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2022-06-06 deposited with the CCDC.	2023-04-06 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            'C12 H12 Cu N2 O4'
_chemical_formula_weight         311.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   4.1453(3)
_cell_length_b                   6.0280(5)
_cell_length_c                   11.9507(9)
_cell_angle_alpha                95.652(4)
_cell_angle_beta                 93.881(4)
_cell_angle_gamma                98.430(4)
_cell_volume                     292.94(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3619
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      27.72

_exptl_crystal_description       plate
_exptl_crystal_colour            blue


_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_F_000             159
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.876
_shelx_estimated_absorpt_T_min   0.603
_shelx_estimated_absorpt_T_max   0.912

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.721
_exptl_absorpt_correction_T_max  0.910

_exptl_absorpt_process_details   'SADABS (Bruker,2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)


_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8936
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.437
_diffrn_reflns_theta_max         28.297
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1451
_reflns_number_gt                1167
_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.
 
 _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       'BRUKER SMART (Bruker, 2014)'
_computing_cell_refinement       'BRUKER SMART (Bruker, 2014)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury 2020.1'
_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)+0.4525P] 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_number_reflns         1451
_refine_ls_number_parameters     97
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.0767
_refine_ls_wR_factor_gt          0.0709
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.077
_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 0.8878(7) 0.2030(5) 0.8162(2) 0.0223(6) Uani 1 1 d . . . . .
C2 C 0.7565(7) 0.0938(4) 0.7000(2) 0.0215(6) Uani 1 1 d . . . . .
C3 C 0.5759(6) 0.2037(5) 0.6303(2) 0.0222(6) Uani 1 1 d . . . . .
H3 H 0.5264 0.3443 0.6564 0.027 Uiso 1 1 calc R U . . .
C4 C 0.4622(7) 0.1077(4) 0.5190(2) 0.0209(6) Uani 1 1 d . . . . .
C5 C 0.2776(7) 0.2189(5) 0.4449(2) 0.0253(6) Uani 1 1 d . . . . .
H5 H 0.2270 0.3601 0.4693 0.030 Uiso 1 1 calc R U . . .
C6 C 0.1722(7) 0.1218(5) 0.3379(2) 0.0252(6) Uani 1 1 d . . . . .
H6 H 0.0529 0.1980 0.2899 0.030 Uiso 1 1 calc R U . . .
O1 O 0.8131(5) 0.3972(3) 0.84517(15) 0.0301(5) Uani 1 1 d . . . . .
O2 O 1.0611(5) 0.1071(3) 0.87790(15) 0.0333(5) Uani 1 1 d . . . . .
N1 N 0.6575(6) 0.2954(4) 1.0638(2) 0.0293(6) Uani 1 1 d D . . . .
Cu1 Cu 1.0000 0.5000 1.0000 0.02759(17) Uani 1 2 d S . P . .
H1N H 0.743(7) 0.185(4) 1.091(2) 0.033 Uiso 1 1 d D U . . .
H2N H 0.501(6) 0.239(5) 1.012(2) 0.033 Uiso 1 1 d D U . . .
H3N H 0.578(7) 0.362(5) 1.120(2) 0.033 Uiso 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 O2 1.236(3) . ?
C1 O1 1.276(3) . ?
C1 C2 1.507(3) . ?
C2 C3 1.365(4) . ?
C2 C6 1.413(4) 2_656 ?
C3 C4 1.418(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.412(4) . ?
C4 C4 1.419(5) 2_656 ?
C5 C6 1.368(3) . ?
C5 H5 0.9300 . ?
C6 C2 1.413(4) 2_656 ?
C6 H6 0.9300 . ?
O1 Cu1 1.9615(17) . ?
N1 Cu1 1.984(3) . ?
N1 H1N 0.878(17) . ?
N1 H2N 0.873(18) . ?
N1 H3N 0.861(17) . ?
Cu1 O1 1.9615(17) 2_767 ?
Cu1 N1 1.984(3) 2_767 ?

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
O2 C1 O1 123.1(2) . . ?
O2 C1 C2 120.6(2) . . ?
O1 C1 C2 116.3(2) . . ?
C3 C2 C6 119.8(2) . 2_656 ?
C3 C2 C1 120.5(2) . . ?
C6 C2 C1 119.6(2) 2_656 . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 122.4(2) . . ?
C5 C4 C4 119.0(3) . 2_656 ?
C3 C4 C4 118.6(3) . 2_656 ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C2 120.3(3) . 2_656 ?
C5 C6 H6 119.8 . . ?
C2 C6 H6 119.8 2_656 . ?
C1 O1 Cu1 108.81(16) . . ?
Cu1 N1 H1N 110(2) . . ?
Cu1 N1 H2N 110(2) . . ?
H1N N1 H2N 109(3) . . ?
Cu1 N1 H3N 112(2) . . ?
H1N N1 H3N 105(3) . . ?
H2N N1 H3N 110(3) . . ?
O1 Cu1 O1 180.00(11) . 2_767 ?
O1 Cu1 N1 91.94(9) . . ?
O1 Cu1 N1 88.06(9) 2_767 . ?
O1 Cu1 N1 88.06(9) . 2_767 ?
O1 Cu1 N1 91.94(9) 2_767 2_767 ?
N1 Cu1 N1 180.00(16) . 2_767 ?

_refine_diff_density_max         0.369
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.097

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2177366'
loop_
_audit_author_name
_audit_author_address
'Vania Andre'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2022-06-06 deposited with the CCDC.	2023-04-06 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            'C14 H14 Cu N2 O5'
_chemical_formula_weight         353.82

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.018(7)
_cell_length_b                   5.7985(13)
_cell_length_c                   8.912(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.287(14)
_cell_angle_gamma                90
_cell_volume                     1395.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1998
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      28.26

_exptl_crystal_description       plate
_exptl_crystal_colour            blue


_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_F_000             724
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.591
_shelx_estimated_absorpt_T_min   0.763
_shelx_estimated_absorpt_T_max   0.939

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.826
_exptl_absorpt_correction_T_max  0.938

_exptl_absorpt_process_details   'SADABS (Bruker,2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)


_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7304
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.017
_diffrn_reflns_theta_max         32.026
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             2361
_reflns_number_gt                1722
_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.
 
 _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       'BRUKER SMART (Bruker, 2014)'
_computing_cell_refinement       'BRUKER SMART (Bruker, 2014)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury 2020.1'
_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)+(0.0422P)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_number_reflns         2361
_refine_ls_number_parameters     111
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0859
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.028
_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
Cu01 Cu 0.7500 0.2500 0.5000 0.02863(11) Uani 1 2 d S . P . .
O3 O 0.5000 0.9394(3) 0.7500 0.0378(5) Uani 1 2 d S T P . .
O1 O 0.68332(5) 0.3289(3) 0.56482(16) 0.0382(3) Uani 1 1 d . . . . .
O2 O 0.69827(5) 0.6403(3) 0.43175(17) 0.0426(4) Uani 1 1 d . . . . .
N1 N 0.77860(7) 0.3941(3) 0.68479(19) 0.0367(4) Uani 1 1 d D . . . .
C5 C 0.54042(7) 0.8225(3) 0.6945(2) 0.0287(4) Uani 1 1 d . . . . .
C7 C 0.60793(7) 0.8439(3) 0.5263(2) 0.0311(4) Uani 1 1 d . . . . .
H7 H 0.6250 0.9223 0.4526 0.037 Uiso 1 1 calc R U . . .
C6 C 0.56515(7) 0.9384(3) 0.5823(2) 0.0321(4) Uani 1 1 d . . . . .
H6 H 0.5531 1.0779 0.5453 0.038 Uiso 1 1 calc R U . . .
C3 C 0.60009(7) 0.5203(3) 0.6908(2) 0.0309(4) Uani 1 1 d . . . . .
H3 H 0.6117 0.3794 0.7269 0.037 Uiso 1 1 calc R U . . .
C1 C 0.67224(7) 0.5310(3) 0.51956(19) 0.0287(4) Uani 1 1 d . . . . .
C2 C 0.62575(6) 0.6325(3) 0.57879(19) 0.0262(3) Uani 1 1 d . . . . .
C4 C 0.55746(7) 0.6144(3) 0.7498(2) 0.0345(4) Uani 1 1 d . . . . .
H4 H 0.5407 0.5385 0.8253 0.041 Uiso 1 1 calc R U . . .
H1N H 0.8025(8) 0.312(4) 0.713(3) 0.041 Uiso 1 1 d D U . . .
H2N H 0.7856(8) 0.534(3) 0.657(3) 0.041 Uiso 1 1 d D U . . .
H3N H 0.7585(8) 0.395(4) 0.756(2) 0.041 Uiso 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
Cu01 O1 1.9584(14) . ?
Cu01 O1 1.9585(14) 7_656 ?
Cu01 N1 1.9874(19) 7_656 ?
Cu01 N1 1.9874(19) . ?
O3 C5 1.3863(19) . ?
O3 C5 1.3863(19) 2_656 ?
O1 C1 1.272(2) . ?
O2 C1 1.238(2) . ?
N1 H1N 0.836(17) . ?
N1 H2N 0.867(16) . ?
N1 H3N 0.843(16) . ?
C5 C4 1.379(3) . ?
C5 C6 1.388(2) . ?
C7 C6 1.383(2) . ?
C7 C2 1.394(3) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
C3 C4 1.389(2) . ?
C3 C2 1.390(2) . ?
C3 H3 0.9300 . ?
C1 C2 1.494(2) . ?
C4 H4 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 Cu01 O1 180.00(3) . 7_656 ?
O1 Cu01 N1 89.97(7) . 7_656 ?
O1 Cu01 N1 90.03(7) 7_656 7_656 ?
O1 Cu01 N1 90.03(7) . . ?
O1 Cu01 N1 89.97(7) 7_656 . ?
N1 Cu01 N1 180.00(6) 7_656 . ?
C5 O3 C5 121.4(2) . 2_656 ?
C1 O1 Cu01 109.46(11) . . ?
Cu01 N1 H1N 106.7(18) . . ?
Cu01 N1 H2N 104.0(15) . . ?
H1N N1 H2N 116(2) . . ?
Cu01 N1 H3N 112.2(17) . . ?
H1N N1 H3N 107(2) . . ?
H2N N1 H3N 111(2) . . ?
C4 C5 O3 124.04(16) . . ?
C4 C5 C6 121.27(16) . . ?
O3 C5 C6 114.58(17) . . ?
C6 C7 C2 120.84(16) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
C7 C6 C5 119.19(17) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C4 C3 C2 121.29(17) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
O2 C1 O1 122.59(17) . . ?
O2 C1 C2 121.01(16) . . ?
O1 C1 C2 116.40(15) . . ?
C3 C2 C7 118.61(15) . . ?
C3 C2 C1 120.39(16) . . ?
C7 C2 C1 120.97(15) . . ?
C5 C4 C3 118.79(16) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.074

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2177367'
loop_
_audit_author_name
_audit_author_address
'Vania Andre'
;Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2022-06-06 deposited with the CCDC.	2023-04-06 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            'C22 H20 Cu N2 O4'
_chemical_formula_weight         439.94

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.005(4)
_cell_length_b                   5.9694(13)
_cell_length_c                   8.7828(18)
_cell_angle_alpha                90
_cell_angle_beta                 91.219(8)
_cell_angle_gamma                90
_cell_volume                     943.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9216
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      28.49

_exptl_crystal_description       Plate
_exptl_crystal_colour            Blue


_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_F_000             454
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.190
_shelx_estimated_absorpt_T_min   0.648
_shelx_estimated_absorpt_T_max   0.988

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_T_max  0.988

_exptl_absorpt_process_details   'SADABS (Bruker,2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)


_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30492
_diffrn_reflns_av_unetI/netI     0.0733
_diffrn_reflns_av_R_equivalents  0.1006
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.263
_diffrn_reflns_theta_max         32.081
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.803
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.803
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.803
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2634
_reflns_number_gt                1864
_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.
 
 _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       'BRUKER SMART (Bruker, 2014)'
_computing_cell_refinement       'BRUKER SMART (Bruker, 2014)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury 2020.1'
_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)+(0.0092P)²+1.5841P] 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_number_reflns         2634
_refine_ls_number_parameters     142
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.0988
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.138
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.003

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 0.61386(14) 0.2925(5) 0.4861(3) 0.0275(6) Uani 1 1 d . . . . .
C2 C 0.68440(14) 0.3964(5) 0.4291(3) 0.0250(6) Uani 1 1 d . . . . .
C3 C 0.72773(14) 0.2841(5) 0.3288(3) 0.0254(6) Uani 1 1 d . . . . .
H3 H 0.7125 0.1447 0.2927 0.030 Uiso 1 1 calc R U . . .
C4 C 0.79556(14) 0.3760(5) 0.2784(3) 0.0265(6) Uani 1 1 d . . . . .
C5 C 0.84179(15) 0.2611(5) 0.1765(3) 0.0350(7) Uani 1 1 d . . . . .
H5 H 0.8271 0.1223 0.1383 0.042 Uiso 1 1 calc R U . . .
C6 C 0.90769(17) 0.3514(6) 0.1334(4) 0.0447(8) Uani 1 1 d . . . . .
H6 H 0.9375 0.2738 0.0662 0.054 Uiso 1 1 calc R U . . .
C7 C 0.93058(17) 0.5594(6) 0.1894(4) 0.0483(9) Uani 1 1 d . . . . .
H7 H 0.9758 0.6186 0.1601 0.058 Uiso 1 1 calc R U . . .
C8 C 0.88730(16) 0.6765(6) 0.2867(4) 0.0391(7) Uani 1 1 d . . . . .
H8 H 0.9032 0.8154 0.3227 0.047 Uiso 1 1 calc R U . . .
C9 C 0.81815(14) 0.5892(5) 0.3340(3) 0.0281(6) Uani 1 1 d . . . . .
C10 C 0.77133(15) 0.7037(5) 0.4345(3) 0.0327(6) Uani 1 1 d . . . . .
H10 H 0.7849 0.8451 0.4698 0.039 Uiso 1 1 calc R U . . .
C11 C 0.70659(15) 0.6107(5) 0.4807(3) 0.0317(6) Uani 1 1 d . . . . .
H11 H 0.6766 0.6893 0.5471 0.038 Uiso 1 1 calc R U . . .
N1 N 0.45753(14) 0.1415(5) 0.3141(3) 0.0365(6) Uani 1 1 d D . . . .
O1 O 0.59927(11) 0.0951(4) 0.4401(2) 0.0386(5) Uani 1 1 d . . . . .
O2 O 0.57342(11) 0.3996(4) 0.5711(3) 0.0430(6) Uani 1 1 d . . . . .
Cu01 Cu 0.5000 0.0000 0.5000 0.02819(14) Uani 1 2 d S . P . .
H1N H 0.4888(14) 0.138(5) 0.238(3) 0.034 Uiso 1 1 d D U . . .
H2N H 0.4448(16) 0.278(3) 0.339(3) 0.034 Uiso 1 1 d D U . . .
H3N H 0.4178(13) 0.070(5) 0.275(3) 0.034 Uiso 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 O2 1.233(3) . ?
C1 O1 1.271(3) . ?
C1 C2 1.508(3) . ?
C2 C3 1.365(4) . ?
C2 C11 1.413(4) . ?
C3 C4 1.418(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.413(4) . ?
C4 C9 1.419(4) . ?
C5 C6 1.364(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.394(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.362(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.420(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.410(4) . ?
C10 C11 1.361(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
N1 Cu01 1.978(3) . ?
N1 H1N 0.882(17) . ?
N1 H2N 0.876(17) . ?
N1 H3N 0.892(17) . ?
O1 Cu01 1.9580(19) . ?
Cu01 O1 1.9580(19) 3_656 ?
Cu01 N1 1.978(3) 3_656 ?

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
O2 C1 O1 123.5(2) . . ?
O2 C1 C2 120.0(3) . . ?
O1 C1 C2 116.5(2) . . ?
C3 C2 C11 119.4(2) . . ?
C3 C2 C1 120.6(3) . . ?
C11 C2 C1 120.0(2) . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 122.2(3) . . ?
C5 C4 C9 119.0(2) . . ?
C3 C4 C9 118.8(2) . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.8(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C4 118.6(2) . . ?
C10 C9 C8 123.0(3) . . ?
C4 C9 C8 118.4(3) . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C2 120.8(3) . . ?
C10 C11 H11 119.6 . . ?
C2 C11 H11 119.6 . . ?
Cu01 N1 H1N 112(2) . . ?
Cu01 N1 H2N 107(2) . . ?
H1N N1 H2N 112(3) . . ?
Cu01 N1 H3N 114(2) . . ?
H1N N1 H3N 103(3) . . ?
H2N N1 H3N 109(3) . . ?
C1 O1 Cu01 111.54(17) . . ?
O1 Cu01 O1 180.0 3_656 . ?
O1 Cu01 N1 90.38(10) 3_656 . ?
O1 Cu01 N1 89.62(10) . . ?
O1 Cu01 N1 89.62(10) 3_656 3_656 ?
O1 Cu01 N1 90.38(10) . 3_656 ?
N1 Cu01 N1 180.0 . 3_656 ?

_refine_diff_density_max         0.439
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.090

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

