# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 2006301'
_audit_update_record             
;
2020-10-02 deposited with the CCDC.	2020-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H26 Cu2 N2 O10'
_chemical_formula_weight         605.53

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'
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'
O O 0.0106 0.0060 '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                   9.7692(18)
_cell_length_b                   6.5564(12)
_cell_length_c                   19.064(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.926(7)
_cell_angle_gamma                90
_cell_volume                     1220.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2266
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      23.98

_exptl_crystal_description       rod-like
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_F_000             620
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.802
_shelx_estimated_absorpt_T_min   0.774
_shelx_estimated_absorpt_T_max   0.840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_T_max  0.840
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13193
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.086
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        25.242
_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             2668
_reflns_number_gt                1963
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0369P)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         2668
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0768
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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 0.48068(4) -0.15456(5) 0.05903(2) 0.03014(13) Uani 1 1 d . . . . .
O1 O 0.58330(19) 0.0959(3) 0.03957(9) 0.0294(4) Uani 1 1 d . . . . .
O2 O 0.4060(2) -0.4259(3) 0.07724(10) 0.0409(5) Uani 1 1 d . . . . .
O3 O 0.3808(3) -0.6531(3) 0.16262(11) 0.0525(6) Uani 1 1 d . . . . .
O5 O 0.2961(2) 0.0078(3) 0.09945(12) 0.0523(6) Uani 1 1 d . . . . .
H5 H 0.321512 0.113940 0.118466 0.063 Uiso 1 1 d R U . . .
N2 N 0.5811(2) -0.2037(3) 0.14623(12) 0.0319(6) Uani 1 1 d . . . . .
O4 O 0.9154(2) 0.6234(3) 0.07917(13) 0.0551(7) Uani 1 1 d . . . . .
C1 C 0.6855(3) 0.1794(4) 0.07935(14) 0.0261(6) Uani 1 1 d . . . . .
C2 C 0.4322(3) -0.4987(4) 0.13833(15) 0.0358(7) Uani 1 1 d . . . . .
C3 C 0.7466(3) 0.3585(4) 0.05774(14) 0.0329(7) Uani 1 1 d . . . . .
H3A H 0.716238 0.419457 0.016006 0.039 Uiso 1 1 calc R U . . .
C4 C 0.7335(3) 0.0860(4) 0.14305(14) 0.0319(7) Uani 1 1 d . . . . .
C5 C 0.6802(3) -0.0955(4) 0.17221(14) 0.0336(7) Uani 1 1 d . . . . .
H5A H 0.720943 -0.140528 0.214201 0.040 Uiso 1 1 calc R U . . .
C6 C 0.8521(3) 0.4484(5) 0.09711(16) 0.0383(7) Uani 1 1 d . . . . .
C7 C 0.5366(3) -0.3847(4) 0.18365(14) 0.0404(8) Uani 1 1 d . . . . .
H7A H 0.496353 -0.345044 0.227441 0.049 Uiso 1 1 calc R U . . .
H7B H 0.614580 -0.472050 0.194456 0.049 Uiso 1 1 calc R U . . .
C8 C 0.8413(3) 0.1837(5) 0.18144(17) 0.0462(8) Uani 1 1 d . . . . .
H8A H 0.873117 0.125318 0.223357 0.055 Uiso 1 1 calc R U . . .
C9 C 0.8694(4) 0.7243(5) 0.01612(18) 0.0537(9) Uani 1 1 d . . . . .
H9A H 0.922679 0.845527 0.009715 0.080 Uiso 1 1 calc R U . . .
H9B H 0.880052 0.634808 -0.023170 0.080 Uiso 1 1 calc R U . . .
H9C H 0.774599 0.760362 0.019519 0.080 Uiso 1 1 calc R U . . .
C10 C 0.9001(3) 0.3589(5) 0.15965(17) 0.0509(9) Uani 1 1 d . . . . .
H10A H 0.971338 0.418479 0.185959 0.061 Uiso 1 1 calc R U . . .
C11 C 0.1908(4) -0.0762(6) 0.1377(2) 0.0830(14) Uani 1 1 d . . . . .
H11A H 0.125463 0.028037 0.148016 0.124 Uiso 1 1 calc R U . . .
H11B H 0.146420 -0.182222 0.110721 0.124 Uiso 1 1 calc R U . . .
H11C H 0.228110 -0.132191 0.180798 0.124 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 N2 1.929(2) . ?
Cu1 O2 1.958(2) . ?
Cu1 O1 1.9659(18) . ?
Cu1 O1 1.9983(18) 3_655 ?
Cu1 O5 2.252(2) . ?
O1 C1 1.350(3) . ?
O2 C2 1.276(3) . ?
O3 C2 1.228(3) . ?
O5 C11 1.394(4) . ?
O5 H5 0.8193 . ?
N2 C5 1.286(4) . ?
N2 C7 1.458(3) . ?
O4 C6 1.352(3) . ?
O4 C9 1.431(4) . ?
C1 C3 1.386(4) . ?
C1 C4 1.425(4) . ?
C2 C7 1.512(4) . ?
C3 C6 1.386(4) . ?
C3 H3A 0.9300 . ?
C4 C8 1.416(4) . ?
C4 C5 1.419(4) . ?
C5 H5A 0.9300 . ?
C6 C10 1.396(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C10 1.356(4) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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 O2 82.94(9) . . ?
N2 Cu1 O1 93.11(8) . . ?
O2 Cu1 O1 171.02(8) . . ?
N2 Cu1 O1 167.65(9) . 3_655 ?
O2 Cu1 O1 103.59(8) . 3_655 ?
O1 Cu1 O1 78.88(8) . 3_655 ?
N2 Cu1 O5 100.02(9) . . ?
O2 Cu1 O5 93.53(9) . . ?
O1 Cu1 O5 95.10(8) . . ?
O1 Cu1 O5 90.13(8) 3_655 . ?
C1 O1 Cu1 127.24(16) . . ?
C1 O1 Cu1 130.75(16) . 3_655 ?
Cu1 O1 Cu1 101.12(8) . 3_655 ?
C2 O2 Cu1 115.92(18) . . ?
C11 O5 Cu1 127.3(2) . . ?
C11 O5 H5 108.8 . . ?
Cu1 O5 H5 108.6 . . ?
C5 N2 C7 119.6(2) . . ?
C5 N2 Cu1 126.5(2) . . ?
C7 N2 Cu1 113.95(18) . . ?
C6 O4 C9 118.1(2) . . ?
O1 C1 C3 119.6(2) . . ?
O1 C1 C4 121.4(2) . . ?
C3 C1 C4 119.0(3) . . ?
O3 C2 O2 125.5(3) . . ?
O3 C2 C7 118.0(3) . . ?
O2 C2 C7 116.5(3) . . ?
C6 C3 C1 121.3(3) . . ?
C6 C3 H3A 119.4 . . ?
C1 C3 H3A 119.4 . . ?
C8 C4 C5 117.0(3) . . ?
C8 C4 C1 117.6(3) . . ?
C5 C4 C1 125.4(3) . . ?
N2 C5 C4 126.4(3) . . ?
N2 C5 H5A 116.8 . . ?
C4 C5 H5A 116.8 . . ?
O4 C6 C3 124.2(3) . . ?
O4 C6 C10 115.4(3) . . ?
C3 C6 C10 120.4(3) . . ?
N2 C7 C2 109.2(2) . . ?
N2 C7 H7A 109.8 . . ?
C2 C7 H7A 109.8 . . ?
N2 C7 H7B 109.8 . . ?
C2 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
C10 C8 C4 122.7(3) . . ?
C10 C8 H8A 118.6 . . ?
C4 C8 H8A 118.6 . . ?
O4 C9 H9A 109.5 . . ?
O4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 C6 119.0(3) . . ?
C8 C10 H10A 120.5 . . ?
C6 C10 H10A 120.5 . . ?
O5 C11 H11A 109.5 . . ?
O5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_refine_diff_density_max         0.409
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2006302'
_audit_update_record             
;
2020-10-02 deposited with the CCDC.	2020-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 Cu2 N2 O10'
_chemical_formula_weight         577.47

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'
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'
O O 0.0106 0.0060 '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                   9.735(2)
_cell_length_b                   8.646(2)
_cell_length_c                   13.038(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.096(7)
_cell_angle_gamma                90
_cell_volume                     1091.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    706
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      18.26

_exptl_crystal_description       rhombus
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    2.010
_shelx_estimated_absorpt_T_min   0.752
_shelx_estimated_absorpt_T_max   0.809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_T_max  0.809
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9653
_diffrn_reflns_av_unetI/netI     0.1112
_diffrn_reflns_av_R_equivalents  0.1397
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.104
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1924
_reflns_number_gt                1135
_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'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1218P)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         1924
_refine_ls_number_parameters     154
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.1399
_refine_ls_R_factor_gt           0.0778
_refine_ls_wR_factor_ref         0.2237
_refine_ls_wR_factor_gt          0.1955
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.035
_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 0.58084(12) 0.89051(13) -0.06539(9) 0.0332(4) Uani 1 1 d . . . . .
O3 O 0.6135(7) 0.9311(7) 0.0789(5) 0.0354(16) Uani 1 1 d . . . . .
O1 O 0.5559(7) 0.8465(7) -0.2138(5) 0.0383(17) Uani 1 1 d . . . . .
O2 O 0.4706(7) 0.7154(7) -0.0252(5) 0.0442(18) Uani 1 1 d . . . . .
H2B H 0.512938 0.670399 0.026886 0.053 Uiso 1 1 d R U . . .
H2C H 0.457988 0.650460 -0.074224 0.053 Uiso 1 1 d R U . . .
O5 O 0.9076(7) 1.0443(9) 0.3859(5) 0.050(2) Uani 1 1 d . . . . .
O4 O 0.5796(8) 0.9540(8) -0.3643(5) 0.0485(19) Uani 1 1 d . U . . .
N1 N 0.7119(9) 1.0402(9) -0.1036(6) 0.039(2) Uani 1 1 d . . . . .
C7 C 0.7335(10) 0.9944(10) 0.1223(7) 0.035(2) Uani 1 1 d . . . . .
C6 C 0.7595(10) 0.9834(11) 0.2301(7) 0.037(2) Uani 1 1 d . . . . .
H6A H 0.697661 0.931226 0.267369 0.044 Uiso 1 1 calc R U . . .
C8 C 0.8094(10) 1.1012(11) -0.0427(8) 0.038(2) Uani 1 1 d . . . . .
H8A H 0.871871 1.165062 -0.071491 0.045 Uiso 1 1 calc R U . . .
C2 C 0.8776(11) 1.0504(12) 0.2813(8) 0.040(3) Uani 1 1 d . . . . .
C10 C 0.6005(11) 0.9457(12) -0.2659(8) 0.042(3) Uani 1 1 d . U . . .
C5 C 0.8283(11) 1.0771(10) 0.0675(8) 0.042(3) Uani 1 1 d . . . . .
C4 C 0.9432(10) 1.1442(13) 0.1241(8) 0.046(3) Uani 1 1 d . . . . .
H4A H 1.005396 1.198722 0.088371 0.055 Uiso 1 1 calc R U . . .
C3 C 0.9689(11) 1.1342(13) 0.2284(9) 0.052(3) Uani 1 1 d . . . . .
H3A H 1.045630 1.182265 0.263250 0.063 Uiso 1 1 calc R U . . .
C9 C 0.6942(12) 1.0719(11) -0.2147(8) 0.046(3) Uani 1 1 d . U . . .
H9A H 0.783067 1.070794 -0.242071 0.056 Uiso 1 1 calc R U . . .
H9B H 0.652502 1.172865 -0.227820 0.056 Uiso 1 1 calc R U . . .
C1 C 0.8097(12) 0.9763(15) 0.4455(8) 0.060(3) Uani 1 1 d . . . . .
H1A H 0.844177 0.979947 0.517255 0.089 Uiso 1 1 calc R U . . .
H1B H 0.724206 1.032328 0.434824 0.089 Uiso 1 1 calc R U . . .
H1C H 0.794356 0.870599 0.424811 0.089 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 O3 1.906(6) . ?
Cu1 N1 1.920(8) . ?
Cu1 O2 1.959(6) . ?
Cu1 O1 1.962(6) . ?
Cu1 O3 2.433(6) 3_675 ?
O3 C7 1.359(11) . ?
O1 C10 1.203(12) . ?
O2 H2B 0.8501 . ?
O2 H2C 0.8500 . ?
O5 C2 1.366(12) . ?
O5 C1 1.420(13) . ?
O4 C10 1.280(12) . ?
N1 C8 1.283(12) . ?
N1 C9 1.467(12) . ?
C7 C6 1.404(13) . ?
C7 C5 1.419(13) . ?
C6 C2 1.392(14) . ?
C6 H6A 0.9300 . ?
C8 C5 1.444(14) . ?
C8 H8A 0.9300 . ?
C2 C3 1.387(15) . ?
C10 C9 1.530(14) . ?
C5 C4 1.399(14) . ?
C4 C3 1.359(15) . ?
C4 H4A 0.9300 . ?
C3 H3A 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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 Cu1 N1 94.9(3) . . ?
O3 Cu1 O2 85.2(3) . . ?
N1 Cu1 O2 171.2(3) . . ?
O3 Cu1 O1 177.5(3) . . ?
N1 Cu1 O1 83.7(3) . . ?
O2 Cu1 O1 95.8(3) . . ?
O3 Cu1 O3 90.1(2) . 3_675 ?
N1 Cu1 O3 95.0(3) . 3_675 ?
O2 Cu1 O3 93.8(3) . 3_675 ?
O1 Cu1 O3 92.2(2) . 3_675 ?
C7 O3 Cu1 122.1(6) . . ?
C7 O3 Cu1 113.7(5) . 3_675 ?
Cu1 O3 Cu1 89.9(2) . 3_675 ?
C10 O1 Cu1 113.9(7) . . ?
Cu1 O2 H2B 109.6 . . ?
Cu1 O2 H2C 110.4 . . ?
H2B O2 H2C 108.5 . . ?
C2 O5 C1 118.5(8) . . ?
C8 N1 C9 122.4(9) . . ?
C8 N1 Cu1 125.8(7) . . ?
C9 N1 Cu1 111.8(6) . . ?
O3 C7 C6 116.4(8) . . ?
O3 C7 C5 124.7(9) . . ?
C6 C7 C5 118.7(9) . . ?
C2 C6 C7 120.2(9) . . ?
C2 C6 H6A 119.9 . . ?
C7 C6 H6A 119.9 . . ?
N1 C8 C5 124.3(9) . . ?
N1 C8 H8A 117.8 . . ?
C5 C8 H8A 117.8 . . ?
O5 C2 C3 115.9(9) . . ?
O5 C2 C6 122.8(10) . . ?
C3 C2 C6 121.3(10) . . ?
O1 C10 O4 125.3(10) . . ?
O1 C10 C9 119.8(10) . . ?
O4 C10 C9 114.9(10) . . ?
C4 C5 C7 118.0(10) . . ?
C4 C5 C8 118.4(9) . . ?
C7 C5 C8 123.5(9) . . ?
C3 C4 C5 123.6(10) . . ?
C3 C4 H4A 118.2 . . ?
C5 C4 H4A 118.2 . . ?
C4 C3 C2 118.1(9) . . ?
C4 C3 H3A 120.9 . . ?
C2 C3 H3A 120.9 . . ?
N1 C9 C10 107.4(8) . . ?
N1 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
N1 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
O5 C1 H1A 109.5 . . ?
O5 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O5 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_refine_diff_density_max         1.247
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.152

####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2006303'
_audit_update_record             
;
2020-10-02 deposited with the CCDC.	2020-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H11 Cu N O5'
_chemical_formula_weight         288.74

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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   7.4851(4)
_cell_length_b                   13.4109(7)
_cell_length_c                   21.5161(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2159.8(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7029
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      30.98

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.031
_shelx_estimated_absorpt_T_min   0.764
_shelx_estimated_absorpt_T_max   0.807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.764
_exptl_absorpt_correction_T_max  0.807
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22200
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.893
_diffrn_reflns_theta_max         26.988
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2356
_reflns_number_gt                1973
_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'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0619P)²+2.6062P] 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         2356
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1167
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.96488(4) 0.36840(3) 0.11769(2) 0.03411(17) Uani 1 1 d . . . . .
O1 O 1.1431(3) 0.35398(17) 0.05660(9) 0.0379(5) Uani 1 1 d . . . . .
O2 O 0.7790(3) 0.37385(18) 0.17983(9) 0.0442(6) Uani 1 1 d . . . . .
O3 O 0.4894(3) 0.3815(2) 0.19472(11) 0.0517(7) Uani 1 1 d . . . . .
N1 N 0.7702(3) 0.38270(17) 0.06016(10) 0.0289(5) Uani 1 1 d . . . . .
O5 O 1.1343(3) 0.3676(2) 0.18548(10) 0.0679(9) Uani 1 1 d . . . . .
H5D H 1.245348 0.378032 0.185696 0.081 Uiso 1 1 d R U . . .
H5E H 1.091634 0.372933 0.221813 0.081 Uiso 1 1 d R U . . .
O4 O 1.4151(4) 0.3503(2) -0.13684(11) 0.0554(7) Uani 1 1 d . . . . .
C6 C 1.1193(4) 0.3638(2) -0.00350(12) 0.0287(6) Uani 1 1 d . . . . .
C7 C 1.2687(4) 0.3537(2) -0.04216(12) 0.0326(6) Uani 1 1 d . . . . .
H7A H 1.379180 0.339770 -0.024361 0.039 Uiso 1 1 calc R U . . .
C8 C 0.7862(4) 0.3911(2) 0.00089(12) 0.0302(6) Uani 1 1 d . . . . .
H8A H 0.683038 0.402915 -0.022047 0.036 Uiso 1 1 calc R U . . .
C10 C 0.6196(4) 0.3801(2) 0.16007(13) 0.0347(7) Uani 1 1 d . . . . .
C5 C 0.9517(4) 0.3835(2) -0.03241(13) 0.0298(6) Uani 1 1 d . . . . .
C3 C 1.0931(5) 0.3853(3) -0.13474(14) 0.0425(8) Uani 1 1 d . . . . .
H3A H 1.085054 0.393760 -0.177548 0.051 Uiso 1 1 calc R U . . .
C2 C 1.2571(4) 0.3638(2) -0.10604(14) 0.0366(7) Uani 1 1 d . . . . .
C9 C 0.5941(4) 0.3873(2) 0.08985(13) 0.0345(7) Uani 1 1 d . . . . .
H9A H 0.519983 0.332738 0.075353 0.041 Uiso 1 1 calc R U . . .
H9B H 0.535377 0.449555 0.079328 0.041 Uiso 1 1 calc R U . . .
C4 C 0.9451(4) 0.3936(3) -0.09738(14) 0.0391(7) Uani 1 1 d . . . . .
H4A H 0.835324 0.406408 -0.115957 0.047 Uiso 1 1 calc R U . . .
C1 C 1.4156(6) 0.3596(3) -0.20322(16) 0.0591(11) Uani 1 1 d . . . . .
H1A H 1.534274 0.348336 -0.218639 0.089 Uiso 1 1 calc R U . . .
H1B H 1.335737 0.311285 -0.220868 0.089 Uiso 1 1 calc R U . . .
H1C H 1.377252 0.425418 -0.214593 0.089 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 O1 1.883(2) . ?
Cu1 N1 1.921(2) . ?
Cu1 O2 1.931(2) . ?
Cu1 O5 1.933(2) . ?
O1 C6 1.312(3) . ?
O2 C10 1.269(4) . ?
O3 C10 1.227(4) . ?
N1 C8 1.286(3) . ?
N1 C9 1.466(3) . ?
O5 H5D 0.8428 . ?
O5 H5E 0.8474 . ?
O4 C2 1.367(4) . ?
O4 C1 1.434(4) . ?
C6 C7 1.401(4) . ?
C6 C5 1.425(4) . ?
C7 C2 1.384(4) . ?
C7 H7A 0.9300 . ?
C8 C5 1.435(4) . ?
C8 H8A 0.9300 . ?
C10 C9 1.526(4) . ?
C5 C4 1.405(4) . ?
C3 C4 1.373(5) . ?
C3 C2 1.404(5) . ?
C3 H3A 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C4 H4A 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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 95.62(9) . . ?
O1 Cu1 O2 176.21(10) . . ?
N1 Cu1 O2 84.01(10) . . ?
O1 Cu1 O5 93.52(10) . . ?
N1 Cu1 O5 169.80(10) . . ?
O2 Cu1 O5 87.16(10) . . ?
C6 O1 Cu1 125.54(19) . . ?
C10 O2 Cu1 116.61(18) . . ?
C8 N1 C9 120.8(2) . . ?
C8 N1 Cu1 125.2(2) . . ?
C9 N1 Cu1 113.92(17) . . ?
Cu1 O5 H5D 130.6 . . ?
Cu1 O5 H5E 116.6 . . ?
H5D O5 H5E 110.7 . . ?
C2 O4 C1 118.3(3) . . ?
O1 C6 C7 117.8(3) . . ?
O1 C6 C5 124.7(3) . . ?
C7 C6 C5 117.5(2) . . ?
C2 C7 C6 122.0(3) . . ?
C2 C7 H7A 119.0 . . ?
C6 C7 H7A 119.0 . . ?
N1 C8 C5 124.7(3) . . ?
N1 C8 H8A 117.6 . . ?
C5 C8 H8A 117.6 . . ?
O3 C10 O2 122.9(3) . . ?
O3 C10 C9 120.1(3) . . ?
O2 C10 C9 117.0(2) . . ?
C4 C5 C6 118.9(3) . . ?
C4 C5 C8 117.4(3) . . ?
C6 C5 C8 123.7(2) . . ?
C4 C3 C2 117.7(3) . . ?
C4 C3 H3A 121.2 . . ?
C2 C3 H3A 121.2 . . ?
O4 C2 C7 114.5(3) . . ?
O4 C2 C3 124.8(3) . . ?
C7 C2 C3 120.8(3) . . ?
N1 C9 C10 108.4(2) . . ?
N1 C9 H9A 110.0 . . ?
C10 C9 H9A 110.0 . . ?
N1 C9 H9B 110.0 . . ?
C10 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
C3 C4 C5 123.1(3) . . ?
C3 C4 H4A 118.4 . . ?
C5 C4 H4A 118.4 . . ?
O4 C1 H1A 109.5 . . ?
O4 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O4 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

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 H5E O3 0.85 1.96 2.803(3) 178.3 6_656 yes
O5 H5E O2 0.85 2.54 3.095(3) 124.1 6_656 yes
O5 H5D O3 0.84 1.84 2.672(3) 170.1 1_655 yes
O5 H5D O3 0.84 1.84 2.672(3) 170.1 1_655 yes
O5 H5E O2 0.85 2.54 3.095(3) 124.1 6_656 yes
O5 H5E O3 0.85 1.96 2.803(3) 178.3 6_656 yes
O5 H5D O3 0.84 1.84 2.672(3) 170.1 1_655 yes
O5 H5E O2 0.85 2.54 3.095(3) 124.1 6_656 yes
O5 H5E O3 0.85 1.96 2.803(3) 178.3 6_656 yes

_refine_diff_density_max         0.443
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.072

