# 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_t
_database_code_depnum_ccdc_archive 'CCDC 1949508'
loop_
_audit_author_name
_audit_author_address
'Meiling Cheng'
;Changzhou University
China
;
_audit_update_record             
;
2019-08-27 deposited with the CCDC.	2020-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H6 Cu N4 O4'
_chemical_formula_weight         285.71

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                   11.2659(15)
_cell_length_b                   10.3109(14)
_cell_length_c                   8.5702(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.741(3)
_cell_angle_gamma                90
_cell_volume                     995.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2929
_cell_measurement_theta_min      2.677
_cell_measurement_theta_max      29.505

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.906
_exptl_crystal_F_000             572
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    2.204
_shelx_estimated_absorpt_T_min   0.643
_shelx_estimated_absorpt_T_max   0.719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.627
_exptl_absorpt_correction_T_max  0.703
_exptl_absorpt_process_details   SADABS

_exptl_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 Smart Apex CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6775
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.678
_diffrn_reflns_theta_max         30.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2642
_reflns_number_gt                2134
_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, 2005)'
_computing_cell_refinement       'Bruker Smart (Bruker, 2005)'
_computing_data_reduction        'Bruker Saint v7.23A (Bruker, 2005)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0463P)²+0.0953P]
 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         2642
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0863
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_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 0.7492(2) 0.5976(2) 0.5251(3) 0.0274(5) Uani 1 1 d . . . . .
C2 C 0.6756(2) 0.5613(2) 0.6589(3) 0.0222(4) Uani 1 1 d . . . . .
C3 C 0.55686(19) 0.5892(2) 0.6917(2) 0.0198(4) Uani 1 1 d . . . . .
C4 C 0.4606(2) 0.6609(2) 0.6100(2) 0.0219(4) Uani 1 1 d . . . . .
N2 N 0.52917(16) 0.54076(18) 0.8308(2) 0.0209(4) Uani 1 1 d . . . . .
C6 C 0.8901(3) 0.4160(3) 1.1707(3) 0.0391(6) Uani 1 1 d . . . . .
H6 H 0.8830 0.4939 1.2244 0.047 Uiso 1 1 calc R U . . .
C7 C 0.9904(2) 0.3460(4) 1.1587(4) 0.0461(7) Uani 1 1 d . . . . .
H7 H 1.0645 0.3663 1.2013 0.055 Uiso 1 1 calc R U . . .
C8 C 0.8473(2) 0.2486(3) 1.0331(3) 0.0328(6) Uani 1 1 d . . . . .
H8 H 0.8061 0.1880 0.9729 0.039 Uiso 1 1 calc R U . . .
Cu1 Cu 0.62961(2) 0.39886(3) 1.09938(3) 0.02070(10) Uani 1 1 d . . . . .
N1 N 0.62642(16) 0.48174(18) 0.8923(2) 0.0224(4) Uani 1 1 d . . . . .
C5 C 0.7143(2) 0.4922(2) 0.7892(3) 0.0245(5) Uani 1 1 d . . . . .
H5 H 0.7901 0.4582 0.8028 0.029 Uiso 1 1 calc R U . . .
N3 N 0.80060(16) 0.3545(2) 1.0914(2) 0.0238(4) Uani 1 1 d . . . . .
N4 N 0.9620(2) 0.2402(2) 1.0724(3) 0.0405(6) Uani 1 1 d . . . . .
H4 H 1.0089 0.1834 1.0479 0.060(11) Uiso 1 1 d R . . . .
O1 O 0.85413(16) 0.56827(18) 0.5202(2) 0.0355(4) Uani 1 1 d . . . . .
O2 O 0.69961(18) 0.6634(2) 0.4104(2) 0.0448(5) Uani 1 1 d . . . . .
H2 H 0.6297 0.6770 0.4304 0.067 Uiso 1 1 calc R U . . .
O3 O 0.47881(15) 0.71090(17) 0.47911(18) 0.0289(4) Uani 1 1 d . . . . .
O4 O 0.36355(14) 0.66722(17) 0.68167(18) 0.0286(4) 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
C1 O1 1.221(3) . ?
C1 O2 1.313(3) . ?
C1 C2 1.473(3) . ?
C2 C5 1.389(3) . ?
C2 C3 1.400(3) . ?
C3 N2 1.333(3) . ?
C3 C4 1.481(3) . ?
C4 O3 1.254(3) . ?
C4 O4 1.263(3) . ?
N2 N1 1.354(2) . ?
N2 Cu1 1.9934(17) 3_667 ?
C6 C7 1.345(4) . ?
C6 N3 1.365(3) . ?
C6 H6 0.9300 . ?
C7 N4 1.355(4) . ?
C7 H7 0.9300 . ?
C8 N3 1.314(3) . ?
C8 N4 1.335(3) . ?
C8 H8 0.9300 . ?
Cu1 N1 1.9696(18) . ?
Cu1 N3 1.9819(19) . ?
Cu1 N2 1.9934(17) 3_667 ?
Cu1 O4 1.9969(16) 3_667 ?
Cu1 O3 2.3831(17) 2_646 ?
N1 C5 1.340(3) . ?
C5 H5 0.9300 . ?
N4 H4 0.8176 . ?
O2 H2 0.8200 . ?
O3 Cu1 2.3831(17) 2_656 ?
O4 Cu1 1.9969(16) 3_667 ?

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 C1 O2 120.4(2) . . ?
O1 C1 C2 121.3(2) . . ?
O2 C1 C2 118.4(2) . . ?
C5 C2 C3 103.56(18) . . ?
C5 C2 C1 125.6(2) . . ?
C3 C2 C1 130.8(2) . . ?
N2 C3 C2 109.74(19) . . ?
N2 C3 C4 115.55(19) . . ?
C2 C3 C4 134.7(2) . . ?
O3 C4 O4 124.5(2) . . ?
O3 C4 C3 120.1(2) . . ?
O4 C4 C3 115.42(19) . . ?
C3 N2 N1 108.61(17) . . ?
C3 N2 Cu1 111.90(15) . 3_667 ?
N1 N2 Cu1 138.41(14) . 3_667 ?
C7 C6 N3 109.2(3) . . ?
C7 C6 H6 125.4 . . ?
N3 C6 H6 125.4 . . ?
C6 C7 N4 106.3(2) . . ?
C6 C7 H7 126.9 . . ?
N4 C7 H7 126.9 . . ?
N3 C8 N4 110.5(2) . . ?
N3 C8 H8 124.8 . . ?
N4 C8 H8 124.8 . . ?
N1 Cu1 N3 94.31(8) . . ?
N1 Cu1 N2 97.42(7) . 3_667 ?
N3 Cu1 N2 163.50(8) . 3_667 ?
N1 Cu1 O4 174.14(8) . 3_667 ?
N3 Cu1 O4 85.88(7) . 3_667 ?
N2 Cu1 O4 81.27(7) 3_667 3_667 ?
N1 Cu1 O3 95.46(7) . 2_646 ?
N3 Cu1 O3 107.31(7) . 2_646 ?
N2 Cu1 O3 83.12(7) 3_667 2_646 ?
O4 Cu1 O3 90.07(7) 3_667 2_646 ?
C5 N1 N2 107.90(18) . . ?
C5 N1 Cu1 128.65(16) . . ?
N2 N1 Cu1 123.45(13) . . ?
N1 C5 C2 110.2(2) . . ?
N1 C5 H5 124.9 . . ?
C2 C5 H5 124.9 . . ?
C8 N3 C6 106.1(2) . . ?
C8 N3 Cu1 126.79(18) . . ?
C6 N3 Cu1 126.03(17) . . ?
C8 N4 C7 107.9(2) . . ?
C8 N4 H4 127.5 . . ?
C7 N4 H4 124.6 . . ?
C1 O2 H2 109.5 . . ?
C4 O3 Cu1 119.87(14) . 2_656 ?
C4 O4 Cu1 114.59(14) . 3_667 ?

_refine_diff_density_max         0.553
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.089

_shelxl_version_number           2013-2

