# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_ZJNU-14
_database_code_depnum_ccdc_archive 'CCDC 2017484'
loop_
_audit_author_name
_audit_author_address
'Yabing He' 'Zhejiang Normal University'
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-10-22 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         (Me2NH2)[CuL].DMF.H2O
_chemical_formula_sum            'C19 H23 Cu N3 O9'
_chemical_formula_weight         500.94

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'
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      trigonal
_space_group_IT_number           155
_space_group_name_H-M_alt        'R 3 2 :H'
_space_group_name_Hall           'R 3 2"'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'

_cell_length_a                   18.0487(5)
_cell_length_b                   18.0487(5)
_cell_length_c                   36.3959(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     10267.7(6)
_cell_formula_units_Z            18
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    21204
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_F_000             4662
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    1.010
_shelx_estimated_absorpt_T_min   0.863
_shelx_estimated_absorpt_T_max   0.897
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_T_max  0.898
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21204
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         2.257
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5231
_reflns_number_gt                4984
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_max     1.000
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.489(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5231
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0682
_refine_ls_wR_factor_gt          0.0669
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.002
_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 0.83246(2) 1.11213(2) 0.69476(2) 0.01355(8) Uani 1 1 d . . . . .
O1 O 0.75103(12) 1.05369(11) 0.61666(5) 0.0206(4) Uani 1 1 d . . . . .
O2 O 0.78170(13) 1.00508(11) 0.66824(4) 0.0215(3) Uani 1 1 d . . . . .
O3 O 0.84421(12) 0.77798(12) 0.66165(5) 0.0233(4) Uani 1 1 d . . . . .
O4 O 0.78523(12) 0.67856(11) 0.61755(5) 0.0224(4) Uani 1 1 d . . . . .
O5 O 0.5681(2) 0.6619(2) 0.54701(9) 0.0863(12) Uani 1 1 d . . . . .
O6 O 0.46352(15) 0.65321(14) 0.42148(7) 0.0500(7) Uani 1 1 d . . . . .
O7 O 0.52518(10) 0.79030(12) 0.40523(5) 0.0236(4) Uani 1 1 d . . . . .
N1 N 0.59266(19) 0.71916(16) 0.52136(7) 0.0393(7) Uani 1 1 d . . . . .
C1 C 0.74712(16) 0.92019(16) 0.61550(7) 0.0206(5) Uani 1 1 d . . . . .
C2 C 0.77687(17) 0.87079(16) 0.63216(7) 0.0210(5) Uani 1 1 d . . . . .
H2A H 0.8031 0.8862 0.6557 0.025 Uiso 1 1 calc R U . . .
C3 C 0.76813(17) 0.79888(16) 0.61440(7) 0.0219(5) Uani 1 1 d . . . . .
C4 C 0.72882(18) 0.77533(17) 0.58044(7) 0.0237(5) Uani 1 1 d . . . . .
H4A H 0.7220 0.7252 0.5688 0.028 Uiso 1 1 calc R U . . .
C5 C 0.69931(19) 0.82392(17) 0.56318(7) 0.0259(6) Uani 1 1 d . . . . .
C6 C 0.70994(18) 0.89864(17) 0.58053(7) 0.0242(5) Uani 1 1 d . . . . .
H6A H 0.6921 0.9339 0.5686 0.029 Uiso 1 1 calc R U . . .
C7 C 0.75938(15) 0.99889(16) 0.63499(7) 0.0185(5) Uani 1 1 d . . . . .
C8 C 0.80275(16) 0.74829(16) 0.63273(7) 0.0179(5) Uani 1 1 d . . . . .
C9 C 0.65682(19) 0.80038(18) 0.52696(7) 0.0258(6) Uani 1 1 d . . . . .
C10 C 0.5485(2) 0.6965(2) 0.48859(8) 0.0401(8) Uani 1 1 d . . . . .
H10A H 0.5034 0.6393 0.4851 0.048 Uiso 1 1 calc R U . . .
C11 C 0.56862(19) 0.75503(16) 0.46097(7) 0.0256(5) Uani 1 1 d . . . . .
C12 C 0.63602(17) 0.83827(17) 0.46606(7) 0.0276(6) Uani 1 1 d . . . . .
H12A H 0.6521 0.8795 0.4470 0.033 Uiso 1 1 calc R U . . .
C13 C 0.67904(18) 0.85989(17) 0.49916(7) 0.0266(6) Uani 1 1 d . . . . .
H13A H 0.7247 0.9166 0.5029 0.032 Uiso 1 1 calc R U . . .
C14 C 0.51424(17) 0.73028(17) 0.42670(7) 0.0254(6) Uani 1 1 d . . . . .


_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 O2 1.9324(16) . ?
Cu1 O4 1.9526(17) 12_666 ?
Cu1 O1 1.9918(17) 10_456 ?
Cu1 O3 1.9940(17) 3_675 ?
Cu1 O7 2.1042(16) 8_665 ?
Cu1 Cu1 2.6448(5) 10_456 ?
O1 C7 1.263(3) . ?
O1 Cu1 1.9918(17) 10_456 ?
O2 C7 1.262(3) . ?
O3 C8 1.246(3) . ?
O3 Cu1 1.9938(17) 2_765 ?
O4 C8 1.261(3) . ?
O4 Cu1 1.9526(17) 12_656 ?
O5 N1 1.295(4) . ?
O6 C14 1.239(3) . ?
O7 C14 1.269(3) . ?
O7 Cu1 2.1042(16) 15_564 ?
N1 C9 1.354(4) . ?
N1 C10 1.378(4) . ?
C1 C2 1.389(3) . ?
C1 C6 1.400(3) . ?
C1 C7 1.502(3) . ?
C2 C3 1.386(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.382(4) . ?
C3 C8 1.497(3) . ?
C4 C5 1.384(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.412(3) . ?
C5 C9 1.477(4) . ?
C6 H6A 0.9500 . ?
C9 C13 1.381(4) . ?
C10 C11 1.370(4) . ?
C10 H10A 0.9500 . ?
C11 C12 1.394(4) . ?
C11 C14 1.510(3) . ?
C12 C13 1.380(4) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?

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 Cu1 O4 172.58(7) . 12_666 ?
O2 Cu1 O1 91.97(8) . 10_456 ?
O4 Cu1 O1 88.55(8) 12_666 10_456 ?
O2 Cu1 O3 88.62(8) . 3_675 ?
O4 Cu1 O3 88.75(8) 12_666 3_675 ?
O1 Cu1 O3 163.12(7) 10_456 3_675 ?
O2 Cu1 O7 94.67(7) . 8_665 ?
O4 Cu1 O7 92.60(7) 12_666 8_665 ?
O1 Cu1 O7 97.37(7) 10_456 8_665 ?
O3 Cu1 O7 99.40(7) 3_675 8_665 ?
O2 Cu1 Cu1 84.41(5) . 10_456 ?
O4 Cu1 Cu1 88.29(5) 12_666 10_456 ?
O1 Cu1 Cu1 83.67(5) 10_456 10_456 ?
O3 Cu1 Cu1 79.60(5) 3_675 10_456 ?
O7 Cu1 Cu1 178.64(5) 8_665 10_456 ?
C7 O1 Cu1 121.06(16) . 10_456 ?
C7 O2 Cu1 122.55(16) . . ?
C8 O3 Cu1 126.50(16) . 2_765 ?
C8 O4 Cu1 117.98(15) . 12_656 ?
C14 O7 Cu1 123.68(18) . 15_564 ?
O5 N1 C9 121.4(3) . . ?
O5 N1 C10 118.0(3) . . ?
C9 N1 C10 120.4(3) . . ?
C2 C1 C6 120.2(2) . . ?
C2 C1 C7 118.6(2) . . ?
C6 C1 C7 121.0(2) . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 C8 118.5(2) . . ?
C4 C3 C8 121.2(2) . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 119.4(2) . . ?
C4 C5 C9 122.1(2) . . ?
C6 C5 C9 118.5(2) . . ?
C1 C6 C5 119.3(2) . . ?
C1 C6 H6A 120.4 . . ?
C5 C6 H6A 120.4 . . ?
O1 C7 O2 126.5(2) . . ?
O1 C7 C1 118.2(2) . . ?
O2 C7 C1 115.2(2) . . ?
O3 C8 O4 126.6(2) . . ?
O3 C8 C3 117.3(2) . . ?
O4 C8 C3 116.1(2) . . ?
N1 C9 C13 119.4(2) . . ?
N1 C9 C5 119.1(2) . . ?
C13 C9 C5 121.5(3) . . ?
C11 C10 N1 121.0(3) . . ?
C11 C10 H10A 119.5 . . ?
N1 C10 H10A 119.5 . . ?
C10 C11 C12 119.1(2) . . ?
C10 C11 C14 119.7(2) . . ?
C12 C11 C14 121.1(2) . . ?
C13 C12 C11 119.0(2) . . ?
C13 C12 H12A 120.5 . . ?
C11 C12 H12A 120.5 . . ?
C12 C13 C9 121.1(3) . . ?
C12 C13 H13A 119.5 . . ?
C9 C13 H13A 119.5 . . ?
O6 C14 O7 125.2(2) . . ?
O6 C14 C11 117.7(2) . . ?
O7 C14 C11 117.1(2) . . ?

_refine_diff_density_max         0.635
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.045



