# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_compound1
_database_code_depnum_ccdc_archive 'CCDC 1881659'
loop_
_audit_author_name
_audit_author_address
'Arpan Hazra'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2018-11-27 deposited with the CCDC.	2019-03-26 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         C21H18CuN2O7,H2O
_chemical_formula_sum            'C21 H20 Cu N2 O8'
_chemical_formula_weight         491.93

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                   7.9154(17)
_cell_length_b                   10.025(2)
_cell_length_c                   13.447(3)
_cell_angle_alpha                88.038(9)
_cell_angle_beta                 89.073(9)
_cell_angle_gamma                70.501(7)
_cell_volume                     1005.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4582
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      24.9

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BLUE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_F_000             506
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.011
_exptl_crystal_size_mid          0.008
_exptl_crystal_size_min          0.006
_exptl_absorpt_coefficient_mu    1.141
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(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            11386
_diffrn_reflns_av_unetI/netI     0.2247
_diffrn_reflns_av_R_equivalents  0.1244
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.730
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             3456
_reflns_number_gt                1488
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT  A'
_computing_structure_solution    'SHELXT (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)+(0.1402P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   NOREF
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3456
_refine_ls_number_parameters     289
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1859
_refine_ls_R_factor_gt           0.0882
_refine_ls_wR_factor_ref         0.2861
_refine_ls_wR_factor_gt          0.2229
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_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 0.73267(15) 0.31977(10) 0.76327(8) 0.0486(5) Uani 1 1 d . . . . .
O1 O 0.9247(10) 0.0753(7) 0.6420(6) 0.074(2) Uani 1 1 d . . . . .
O2 O 0.7328(7) 0.1268(6) 0.7677(4) 0.0411(14) Uani 1 1 d . U . . .
O3 O 0.7566(8) -0.4926(5) 0.7611(4) 0.0420(16) Uani 1 1 d . . . . .
O4 O 0.7206(9) -0.4412(6) 0.9225(5) 0.0569(19) Uani 1 1 d . . . . .
O5 O 0.5961(10) -0.0760(7) 0.6464(5) 0.068(2) Uani 1 1 d . . . . .
H1 H 0.490385 -0.052520 0.607688 0.102 Uiso 1 1 d R U . . .
O6 O 0.5067(11) -0.1831(7) 0.7709(6) 0.072(2) Uani 1 1 d . . . . .
N1 N 0.9694(10) 0.2455(7) 0.8334(5) 0.0398(19) Uani 1 1 d . . . . .
N2 N 0.5336(10) 0.3864(7) 0.6657(6) 0.050(2) Uani 1 1 d . . . . .
C1 C 0.8544(12) 0.0406(8) 0.7136(7) 0.0384(19) Uani 1 1 d . U . . .
C2 C 0.9185(13) -0.1112(9) 0.7546(7) 0.044(2) Uani 1 1 d . . . . .
C3 C 1.0880(13) -0.1585(9) 0.7917(7) 0.051(3) Uani 1 1 d . . . . .
H3 H 1.161584 -0.103620 0.782274 0.061 Uiso 1 1 calc R U . . .
C4 C 1.1515(14) -0.2860(9) 0.8427(7) 0.052(3) Uani 1 1 d . . . . .
H4 H 1.267186 -0.315762 0.868022 0.063 Uiso 1 1 calc R U . . .
C5 C 1.0501(14) -0.3682(9) 0.8567(7) 0.056(3) Uani 1 1 d . . . . .
H5 H 1.096028 -0.454920 0.890682 0.067 Uiso 1 1 calc R U . . .
C6 C 0.8784(13) -0.3249(8) 0.8209(7) 0.050(3) Uani 1 1 d . . . . .
C8 C 0.7742(13) -0.4251(8) 0.8374(8) 0.046(3) Uani 1 1 d . . . . .
C10 C 1.1132(14) 0.2503(9) 0.7901(8) 0.058(3) Uani 1 1 d . . . . .
H10 H 1.104045 0.292158 0.726712 0.069 Uiso 1 1 calc R U . . .
C11 C 1.2814(13) 0.1961(9) 0.8331(7) 0.054(3) Uani 1 1 d . . . . .
H11 H 1.382068 0.203894 0.800279 0.065 Uiso 1 1 calc R U . . .
C12 C 1.2957(12) 0.1297(8) 0.9267(7) 0.045(2) Uani 1 1 d . . . . .
C13 C 1.1416(13) 0.1208(9) 0.9687(7) 0.050(3) Uani 1 1 d . . . . .
H13 H 1.145139 0.073367 1.029738 0.060 Uiso 1 1 calc R U . . .
C14 C 0.9834(14) 0.1814(9) 0.9213(7) 0.054(3) Uani 1 1 d . . . . .
H14 H 0.879408 0.177452 0.952524 0.064 Uiso 1 1 calc R U . . .
C15 C 1.4770(13) 0.0744(8) 0.9800(8) 0.056(3) Uani 1 1 d . . . . .
H15A H 1.570275 0.079453 0.933835 0.067 Uiso 1 1 calc R U . . .
H15B H 1.475321 0.135669 1.034553 0.067 Uiso 1 1 calc R U . . .
C20 C 0.4940(15) 0.3007(11) 0.6025(9) 0.075(4) Uani 1 1 d . . . . .
H20 H 0.571475 0.207878 0.598975 0.090 Uiso 1 1 calc R U . . .
C21 C 0.3493(15) 0.3413(11) 0.5442(9) 0.076(4) Uani 1 1 d . . . . .
H21 H 0.327398 0.274834 0.504409 0.091 Uiso 1 1 calc R U . . .
C17 C 0.2309(14) 0.4787(10) 0.5410(8) 0.061(3) Uani 1 1 d . U . . .
C18 C 0.2739(14) 0.5666(11) 0.6022(8) 0.069(3) Uani 1 1 d . U . . .
H18 H 0.201806 0.661251 0.602959 0.083 Uiso 1 1 calc R U . . .
C19 C 0.4211(15) 0.5203(10) 0.6636(8) 0.075(4) Uani 1 1 d . . . . .
H19 H 0.443226 0.584582 0.705348 0.089 Uiso 1 1 calc R U . . .
C16 C 0.0686(12) 0.5224(11) 0.4774(7) 0.067(3) Uani 1 1 d . . . . .
H16A H 0.025375 0.624599 0.467994 0.080 Uiso 1 1 calc R U . . .
H16B H 0.098756 0.480923 0.412638 0.080 Uiso 1 1 calc R U . . .
C9 C 0.6210(15) -0.1510(9) 0.7294(8) 0.052(3) Uani 1 1 d . . . . .
C7 C 0.8115(14) -0.1955(9) 0.7698(7) 0.049(3) Uani 1 1 d . . . . .
O1W O 0.5549(10) 0.3685(6) 0.9108(5) 0.069(2) Uani 1 1 d . . . . .
H1WA H 0.448870 0.376150 0.942465 0.104 Uiso 1 1 d R U . . .
H1WB H 0.558890 0.459250 0.901085 0.104 Uiso 1 1 d R U . . .
O2W O 0.2729(13) -0.0093(11) 0.5656(7) 0.131(4) Uani 1 1 d . . . . .
H4WA H 0.280813 0.023875 0.499334 0.197 Uiso 1 1 d R U . . .
H4WB H 0.151573 0.014425 0.582433 0.197 Uiso 1 1 d 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
Cu01 O2 1.933(6) . ?
Cu01 O3 1.951(6) 1_565 ?
Cu01 N2 1.988(8) . ?
Cu01 N1 2.008(7) . ?
Cu01 O1W 2.381(7) . ?
O1 C1 1.202(10) . ?
O2 C1 1.291(10) . ?
O3 C8 1.282(10) . ?
O4 C8 1.239(11) . ?
O5 C9 1.304(11) . ?
O6 C9 1.184(12) . ?
N1 C10 1.285(11) . ?
N1 C14 1.314(11) . ?
N2 C19 1.340(11) . ?
N2 C20 1.341(12) . ?
C1 C2 1.521(11) . ?
C2 C3 1.362(12) . ?
C2 C7 1.391(14) . ?
C3 C4 1.370(12) . ?
C4 C5 1.336(14) . ?
C5 C6 1.371(13) . ?
C6 C7 1.388(11) . ?
C6 C8 1.506(14) . ?
C10 C11 1.387(12) . ?
C11 C12 1.391(12) . ?
C12 C13 1.365(13) . ?
C12 C15 1.535(13) . ?
C13 C14 1.355(12) . ?
C15 C15 1.494(15) 2_857 ?
C20 C21 1.338(14) . ?
C21 C17 1.383(13) . ?
C17 C18 1.352(14) . ?
C17 C16 1.486(13) . ?
C18 C19 1.378(14) . ?
C16 C16 1.43(2) 2_566 ?
C9 C7 1.526(15) . ?

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 Cu01 O3 174.6(2) . 1_565 ?
O2 Cu01 N2 94.0(3) . . ?
O3 Cu01 N2 90.6(3) 1_565 . ?
O2 Cu01 N1 86.7(3) . . ?
O3 Cu01 N1 88.2(3) 1_565 . ?
N2 Cu01 N1 166.7(3) . . ?
O2 Cu01 O1W 90.6(2) . . ?
O3 Cu01 O1W 91.5(2) 1_565 . ?
N2 Cu01 O1W 97.6(3) . . ?
N1 Cu01 O1W 95.6(3) . . ?
C1 O2 Cu01 115.0(6) . . ?
C8 O3 Cu01 126.0(6) . 1_545 ?
C10 N1 C14 118.3(8) . . ?
C10 N1 Cu01 120.5(6) . . ?
C14 N1 Cu01 121.0(7) . . ?
C19 N2 C20 115.0(8) . . ?
C19 N2 Cu01 121.5(7) . . ?
C20 N2 Cu01 123.3(6) . . ?
O1 C1 O2 124.8(8) . . ?
O1 C1 C2 121.2(8) . . ?
O2 C1 C2 113.7(8) . . ?
C3 C2 C7 118.3(8) . . ?
C3 C2 C1 115.6(9) . . ?
C7 C2 C1 125.4(9) . . ?
C2 C3 C4 120.8(10) . . ?
C5 C4 C3 121.2(10) . . ?
C4 C5 C6 120.1(9) . . ?
C5 C6 C7 119.4(10) . . ?
C5 C6 C8 117.0(8) . . ?
C7 C6 C8 123.6(9) . . ?
O4 C8 O3 125.3(9) . . ?
O4 C8 C6 118.7(9) . . ?
O3 C8 C6 115.9(9) . . ?
N1 C10 C11 123.2(9) . . ?
C10 C11 C12 118.4(10) . . ?
C13 C12 C11 116.9(9) . . ?
C13 C12 C15 122.5(9) . . ?
C11 C12 C15 120.6(9) . . ?
C14 C13 C12 119.7(9) . . ?
N1 C14 C13 123.4(10) . . ?
C15 C15 C12 113.7(11) 2_857 . ?
C21 C20 N2 123.6(9) . . ?
C20 C21 C17 122.3(11) . . ?
C18 C17 C21 114.1(10) . . ?
C18 C17 C16 123.8(9) . . ?
C21 C17 C16 122.0(10) . . ?
C17 C18 C19 122.0(9) . . ?
N2 C19 C18 122.8(10) . . ?
C16 C16 C17 110.4(10) 2_566 . ?
O6 C9 O5 123.5(11) . . ?
O6 C9 C7 121.8(10) . . ?
O5 C9 C7 114.7(11) . . ?
C6 C7 C2 120.2(9) . . ?
C6 C7 C9 118.3(10) . . ?
C2 C7 C9 121.5(8) . . ?

_refine_diff_density_max         1.229
_refine_diff_density_min         -1.279
_refine_diff_density_rms         0.222


_chemical_properties_physical    Heat-sensitive
