# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_sq
_database_code_depnum_ccdc_archive 'CCDC 2173080'
loop_
_audit_author_name
_audit_author_address
'Junyan Li'
;Shenyang University of chemical technology
China
;
_audit_update_record             
;
2022-05-16 deposited with the CCDC.	2022-09-26 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            'C16 H7 Cu2 N0 O11'
_chemical_formula_weight         502.30

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.860
_cell_length_b                   18.909
_cell_length_c                   14.779
_cell_angle_alpha                90
_cell_angle_beta                 92.13
_cell_angle_gamma                90
_cell_volume                     3032.6
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4192
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      24.37

_exptl_crystal_description       Block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.100
_exptl_crystal_F_000             996
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.438
_shelx_estimated_absorpt_T_min   0.762
_shelx_estimated_absorpt_T_max   0.762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33249
_diffrn_reflns_av_unetI/netI     0.1626
_diffrn_reflns_av_R_equivalents  0.1635
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.750
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             5262
_reflns_number_gt                2511
_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.
 
 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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_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)+(0.0100P)²+50.0000P] 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_number_reflns         5262
_refine_ls_number_parameters     287
_refine_ls_number_restraints     199
_refine_ls_R_factor_all          0.2282
_refine_ls_R_factor_gt           0.1448
_refine_ls_wR_factor_ref         0.2983
_refine_ls_wR_factor_gt          0.2770
_refine_ls_goodness_of_fit_ref   1.217
_refine_ls_restrained_S_all      1.213
_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 0.5242(10) 0.5919(7) 0.2648(9) 0.074(6) Uani 1 1 d D . . . .
C2 C 0.3843(8) 0.5917(5) 0.2646(7) 0.053(4) Uani 1 1 d DG U . . .
C3 C 0.3175(10) 0.5553(5) 0.1974(6) 0.070(5) Uani 1 1 d G . . . .
H3 H 0.3585 0.5307 0.1531 0.084 Uiso 1 1 calc R U . . .
C4 C 0.1895(10) 0.5557(5) 0.1963(6) 0.068(5) Uani 1 1 d G . . . .
H4 H 0.1448 0.5314 0.1514 0.081 Uiso 1 1 calc R U . . .
C5 C 0.1282(8) 0.5925(5) 0.2625(7) 0.066(5) Uani 1 1 d DG . . . .
C6 C 0.1950(10) 0.6289(5) 0.3297(6) 0.059(5) Uani 1 1 d DG . . . .
H6 H 0.1539 0.6536 0.3740 0.071 Uiso 0.366(10) 1 calc R U P A 2
C7 C 0.3230(10) 0.6285(5) 0.3308(6) 0.058(4) Uani 1 1 d DG U . . .
H7 H 0.3677 0.6529 0.3757 0.070 Uiso 0.634(10) 1 calc R U P A 1
C8 C -0.0113(10) 0.5911(8) 0.2607(9) 0.063(5) Uani 1 1 d D . . . .
C12 C 0.2414(15) 0.5989(4) 0.6145(7) 0.067(3) Uani 1 1 d D U . . .
C13 C 0.2408(15) 0.6606(6) 0.6662(6) 0.072(3) Uani 1 1 d D U . . .
H13 H 0.2443 0.6588 0.7291 0.087 Uiso 1 1 calc R U . . .
C14 C 0.2349(17) 0.7256(5) 0.6204(7) 0.079(3) Uani 1 1 d D U . . .
C15 C 0.244(2) 0.5288(5) 0.6624(7) 0.082(6) Uani 1 1 d D U . . .
C16 C 0.2461(13) 0.7936(5) 0.6748(7) 0.044(4) Uani 1 1 d D U . . .
C9A C 0.184(3) 0.7274(6) 0.5329(10) 0.070(4) Uani 0.634(10) 1 d D U P A 1
H9A H 0.1495 0.7689 0.5093 0.084 Uiso 0.634(10) 1 calc R U P A 1
C10A C 0.184(3) 0.6659(7) 0.4812(7) 0.067(3) Uani 0.634(10) 1 d D U P A 1
C11A C 0.204(3) 0.6014(6) 0.5240(9) 0.067(4) Uani 0.634(10) 1 d D U P A 1
H11A H 0.1920 0.5596 0.4917 0.080 Uiso 0.634(10) 1 calc R U P A 1
O11A O 0.1444(15) 0.6782(7) 0.3892(7) 0.068(4) Uani 0.634(10) 1 d D U P A 1
C9B C 0.319(4) 0.7278(9) 0.5416(16) 0.070(4) Uani 0.366(10) 1 d D U P A 2
H9B H 0.3675 0.7666 0.5288 0.085 Uiso 0.366(10) 1 calc R U P A 2
C10B C 0.316(4) 0.6667(9) 0.4900(13) 0.068(3) Uani 0.366(10) 1 d D U P A 2
C11B C 0.299(4) 0.6009(8) 0.5307(17) 0.067(4) Uani 0.366(10) 1 d D U P A 2
H11B H 0.3248 0.5596 0.5032 0.080 Uiso 0.366(10) 1 calc R U P A 2
O11B O 0.365(2) 0.6741(11) 0.4018(10) 0.070(5) Uani 0.366(10) 1 d D U P A 2
Cu1 Cu 0.75822(19) 0.62422(9) 0.33779(13) 0.0538(6) Uani 1 1 d . . . . .
Cu2 Cu 0.2504(2) 0.94347(8) 0.68156(13) 0.0547(7) Uani 1 1 d . . . . .
O1 O 0.7734(15) 0.6755(7) 0.4679(9) 0.117(5) Uani 1 1 d . . . . .
O2 O 0.5741(12) 0.5617(6) 0.2002(7) 0.080(4) Uani 1 1 d D . . . .
O3 O 0.5860(11) 0.6197(5) 0.3288(7) 0.069(3) Uani 1 1 d D . . . .
O4 O -0.0660(11) 0.5630(5) 0.1946(8) 0.074(3) Uani 1 1 d D . . . .
H4O H -0.1395 0.5595 0.2046 0.089 Uiso 0.5 1 calc R U P . .
O5 O -0.0644(10) 0.6169(6) 0.3262(7) 0.069(3) Uani 1 1 d D . . . .
H5O H -0.1389 0.6108 0.3194 0.083 Uiso 0.5 1 calc R U P . .
O6 O 0.2442(11) 0.4742(4) 0.6149(7) 0.063(3) Uani 1 1 d D U . . .
O7 O 0.2417(11) 0.5304(5) 0.7463(7) 0.062(3) Uani 1 1 d D . . . .
O8 O 0.2572(12) 0.7903(4) 0.7572(6) 0.073(4) Uani 1 1 d D . . . .
O9 O 0.2431(12) 0.8485(5) 0.6286(7) 0.074(3) Uani 1 1 d D U . . .
O10 O 0.2385(14) 0.9920(6) 0.5519(8) 0.100(5) 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 O2 1.254(9) . ?
C1 O3 1.255(9) . ?
C1 C2 1.519(9) . ?
C2 C3 1.3900 . ?
C2 C7 1.3900 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 C8 1.515(9) . ?
C6 C7 1.3900 . ?
C6 O11A 1.407(9) . ?
C6 H6 0.9300 . ?
C7 O11B 1.421(10) . ?
C7 H7 0.9300 . ?
C8 O5 1.243(9) . ?
C8 O4 1.244(9) . ?
C12 C11A 1.385(8) . ?
C12 C13 1.396(8) . ?
C12 C11B 1.408(9) . ?
C12 C15 1.502(9) . ?
C13 C14 1.402(8) . ?
C13 H13 0.9300 . ?
C14 C9A 1.390(9) . ?
C14 C9B 1.50(3) . ?
C14 C16 1.519(8) . ?
C15 O7 1.241(8) . ?
C15 O6 1.249(8) . ?
C16 O8 1.221(8) . ?
C16 O9 1.242(8) . ?
C9A C10A 1.391(9) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.387(8) . ?
C10A O11A 1.430(9) . ?
C11A H11A 0.9300 . ?
C9B C10B 1.384(10) . ?
C9B H9B 0.9300 . ?
C10B C11B 1.397(10) . ?
C10B O11B 1.435(10) . ?
C11B H11B 0.9300 . ?
Cu1 O3 1.872(12) . ?
Cu1 O5 1.946(12) 1_655 ?
Cu1 O6 1.988(9) 3_666 ?
Cu1 O8 2.007(8) 4_675 ?
Cu1 O1 2.154(12) . ?
Cu1 Cu2 2.638(3) 4_675 ?
Cu2 O2 1.947(13) 4_576 ?
Cu2 O9 1.960(9) . ?
Cu2 O7 1.960(9) 2_556 ?
Cu2 O4 2.000(12) 4_676 ?
Cu2 O10 2.124(11) . ?
Cu2 Cu1 2.638(3) 4_576 ?
O2 Cu2 1.947(13) 4_675 ?
O4 Cu2 2.000(12) 4_575 ?
O4 H4O 0.8200 . ?
O5 Cu1 1.946(12) 1_455 ?
O5 H5O 0.8200 . ?
O6 Cu1 1.988(9) 3_666 ?
O7 Cu2 1.960(9) 2_546 ?
O8 Cu1 2.007(8) 4_576 ?

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 O3 122.1(11) . . ?
O2 C1 C2 117.2(11) . . ?
O3 C1 C2 120.7(11) . . ?
C3 C2 C7 120.0 . . ?
C3 C2 C1 119.9(9) . . ?
C7 C2 C1 120.1(9) . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 C8 121.0(9) . . ?
C4 C5 C8 118.9(9) . . ?
C5 C6 C7 120.0 . . ?
C5 C6 O11A 124.7(10) . . ?
C7 C6 O11A 114.2(10) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 120.0 . . ?
C6 C7 O11B 107.5(14) . . ?
C2 C7 O11B 132.3(13) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
O5 C8 O4 123.9(11) . . ?
O5 C8 C5 118.1(11) . . ?
O4 C8 C5 118.0(11) . . ?
C11A C12 C13 119.5(6) . . ?
C13 C12 C11B 117.9(9) . . ?
C11A C12 C15 119.0(10) . . ?
C13 C12 C15 118.7(8) . . ?
C11B C12 C15 116.1(13) . . ?
C12 C13 C14 118.1(5) . . ?
C12 C13 H13 121.0 . . ?
C14 C13 H13 121.0 . . ?
C9A C14 C13 118.7(7) . . ?
C13 C14 C9B 112.3(14) . . ?
C9A C14 C16 119.6(10) . . ?
C13 C14 C16 119.0(9) . . ?
C9B C14 C16 110.3(14) . . ?
O7 C15 O6 125.7(10) . . ?
O7 C15 C12 116.6(9) . . ?
O6 C15 C12 117.7(10) . . ?
O8 C16 O9 126.2(10) . . ?
O8 C16 C14 119.2(9) . . ?
O9 C16 C14 114.6(9) . . ?
C14 C9A C10A 118.7(7) . . ?
C14 C9A H9A 120.7 . . ?
C10A C9A H9A 120.7 . . ?
C11A C10A C9A 119.3(6) . . ?
C11A C10A O11A 127.8(10) . . ?
C9A C10A O11A 112.2(10) . . ?
C10A C11A C12 120.3(6) . . ?
C10A C11A H11A 119.8 . . ?
C12 C11A H11A 119.8 . . ?
C6 O11A C10A 112.0(12) . . ?
C10B C9B C14 113.8(15) . . ?
C10B C9B H9B 123.1 . . ?
C14 C9B H9B 123.1 . . ?
C9B C10B C11B 120.4(11) . . ?
C9B C10B O11B 114.8(15) . . ?
C11B C10B O11B 122.5(15) . . ?
C10B C11B C12 118.3(9) . . ?
C10B C11B H11B 120.8 . . ?
C12 C11B H11B 120.8 . . ?
C7 O11B C10B 119.4(17) . . ?
O3 Cu1 O5 168.7(4) . 1_655 ?
O3 Cu1 O6 87.5(5) . 3_666 ?
O5 Cu1 O6 89.4(5) 1_655 3_666 ?
O3 Cu1 O8 90.6(5) . 4_675 ?
O5 Cu1 O8 89.4(5) 1_655 4_675 ?
O6 Cu1 O8 164.2(4) 3_666 4_675 ?
O3 Cu1 O1 97.3(5) . . ?
O5 Cu1 O1 93.9(5) 1_655 . ?
O6 Cu1 O1 96.2(5) 3_666 . ?
O8 Cu1 O1 99.5(5) 4_675 . ?
O3 Cu1 Cu2 85.2(3) . 4_675 ?
O5 Cu1 Cu2 83.6(3) 1_655 4_675 ?
O6 Cu1 Cu2 81.6(3) 3_666 4_675 ?
O8 Cu1 Cu2 82.7(3) 4_675 4_675 ?
O1 Cu1 Cu2 176.6(4) . 4_675 ?
O2 Cu2 O9 89.1(5) 4_576 . ?
O2 Cu2 O7 89.3(5) 4_576 2_556 ?
O9 Cu2 O7 170.6(4) . 2_556 ?
O2 Cu2 O4 164.9(5) 4_576 4_676 ?
O9 Cu2 O4 90.4(5) . 4_676 ?
O7 Cu2 O4 88.6(5) 2_556 4_676 ?
O2 Cu2 O10 97.0(5) 4_576 . ?
O9 Cu2 O10 92.0(4) . . ?
O7 Cu2 O10 97.3(4) 2_556 . ?
O4 Cu2 O10 98.1(5) 4_676 . ?
O2 Cu2 Cu1 81.5(3) 4_576 4_576 ?
O9 Cu2 Cu1 84.5(3) . 4_576 ?
O7 Cu2 Cu1 86.1(3) 2_556 4_576 ?
O4 Cu2 Cu1 83.5(3) 4_676 4_576 ?
O10 Cu2 Cu1 176.2(4) . 4_576 ?
C1 O2 Cu2 125.8(9) . 4_675 ?
C1 O3 Cu1 125.3(9) . . ?
C8 O4 Cu2 123.2(9) . 4_575 ?
C8 O4 H4O 109.5 . . ?
Cu2 O4 H4O 15.9 4_575 . ?
C8 O5 Cu1 125.8(9) . 1_455 ?
C8 O5 H5O 109.5 . . ?
Cu1 O5 H5O 17.2 1_455 . ?
C15 O6 Cu1 125.1(8) . 3_666 ?
C15 O7 Cu2 121.4(7) . 2_546 ?
C16 O8 Cu1 123.3(7) . 4_576 ?
C16 O9 Cu2 123.1(8) . . ?

_refine_diff_density_max         1.369
_refine_diff_density_min         -1.874
_refine_diff_density_rms         0.161



