# 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 2021

####################################################################### 
# 
# 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 2052456'
loop_
_audit_author_name
_audit_author_address
'Zhang Heyi'
;Northeast Normal University
China
;
_audit_update_record             
;
2020-12-25 deposited with the CCDC.	2021-07-20 downloaded from the CCDC.
;
_audit_creation_date             2020-12-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H8 O8 Zn, C26 H20 N4, 2(H2 O)'
_chemical_formula_sum            'C42 H32 N4 O10 Zn'
_chemical_formula_weight         818.08
_chemical_melting_point          ?
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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.270(2)
_cell_length_b                   12.2947(12)
_cell_length_c                   14.7085(12)
_cell_angle_alpha                90
_cell_angle_beta                 97.489(3)
_cell_angle_gamma                90
_cell_volume                     3813.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9506
_cell_measurement_temperature    297.2
_cell_measurement_theta_max      25.88
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   0.843
_shelx_estimated_absorpt_T_min   0.815
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0912 before and 0.0570 after correction.
The Ratio of minimum to maximum transmission is 0.8248.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1688
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27119
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.095
_diffrn_reflns_theta_min         2.445
_diffrn_ambient_temperature      297.2
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.9
_diffrn_source_power             0.0405
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3068
_reflns_number_total             3775
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3775
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+3.5618P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0938
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 H1WA-O1W
 0.85 with sigma of 0.02
 N2-H1WA
 2.1 with sigma of 0.02
 O2-H1WB
 2 with sigma of 0.02
 O1W-H1WB
 0.93 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C18(H18), C20(H20), C21(H21), C11(H11), C3(H3), C13(H13), C15(H15),
 C2(H2), C17(H17), C9(H9), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Zn1 Zn 0.500000 0.01994(3) 0.750000 0.02996(12) Uani 1 2 d S T P . .
O4 O 0.54513(8) 0.05769(14) 0.35369(10) 0.0409(4) Uani 1 1 d . . . . .
N1 N 0.94204(8) 0.73391(13) 0.48270(11) 0.0269(4) Uani 1 1 d . . . . .
O1 O 0.55137(9) 0.10038(15) 0.67303(11) 0.0517(5) Uani 1 1 d . . . . .
O2 O 0.60312(10) 0.23265(17) 0.75269(11) 0.0626(6) Uani 1 1 d D . . . .
C1 C 0.61134(10) 0.19061(17) 0.43079(14) 0.0298(5) Uani 1 1 d . . . . .
O3 O 0.59653(11) 0.16609(18) 0.26947(11) 0.0699(7) Uani 1 1 d . . . . .
C4 C 0.59127(10) 0.16126(16) 0.51324(13) 0.0252(4) Uani 1 1 d . . . . .
H4 H 0.561375 0.106159 0.513886 0.030 Uiso 1 1 calc R U . . .
C6 C 0.98769(9) 0.94365(17) 0.49636(13) 0.0266(4) Uani 1 1 d . . . . .
C8 C 0.61464(11) 0.21197(18) 0.59474(14) 0.0314(5) Uani 1 1 d . . . . .
C10 C 0.58274(11) 0.13494(19) 0.34334(14) 0.0349(5) Uani 1 1 d . . . . .
C12 C 0.84750(11) 0.61508(17) 0.47201(15) 0.0316(5) Uani 1 1 d . . . . .
C14 C 0.91813(11) 0.61944(17) 0.47628(15) 0.0337(5) Uani 1 1 d . . . . .
H14A H 0.937330 0.578744 0.529232 0.040 Uiso 1 1 calc R U . . .
H14B H 0.930584 0.585425 0.421867 0.040 Uiso 1 1 calc R U . . .
O1W O 0.58998(12) 0.4654(3) 0.76165(19) 0.0833(7) Uani 1 1 d D . . . .
C16 C 0.58865(12) 0.1802(2) 0.68162(14) 0.0376(5) Uani 1 1 d . . . . .
C18 C 0.81982(11) 0.60490(18) 0.55114(17) 0.0373(5) Uani 1 1 d . . . . .
H18 H 0.844910 0.600834 0.607753 0.045 Uiso 1 1 calc R U . . .
C20 C 0.97432(11) 0.88633(19) 0.57252(14) 0.0362(5) Uani 1 1 d . . . . .
H20 H 0.980921 0.918950 0.630020 0.043 Uiso 1 1 calc R U . . .
C21 C 0.95160(11) 0.78265(19) 0.56426(14) 0.0355(5) Uani 1 1 d . . . . .
H21 H 0.942677 0.745495 0.616145 0.043 Uiso 1 1 calc R U . . .
C11 C 0.65666(13) 0.2714(2) 0.43037(17) 0.0472(6) Uani 1 1 d . . . . .
H11 H 0.670644 0.292064 0.375596 0.057 Uiso 1 1 calc R U . . .
C3 C 0.95448(14) 0.78612(19) 0.40759(15) 0.0449(6) Uani 1 1 d . . . . .
H3 H 0.947463 0.751451 0.350980 0.054 Uiso 1 1 calc R U . . .
C13 C 0.97745(14) 0.89011(19) 0.41298(15) 0.0481(7) Uani 1 1 d . . . . .
H13 H 0.986279 0.925215 0.360089 0.058 Uiso 1 1 calc R U . . .
C7 C 0.75406(13) 0.6007(2) 0.5459(2) 0.0520(7) Uani 1 1 d . . . . .
C15 C 0.80937(15) 0.6218(2) 0.38836(19) 0.0577(7) Uani 1 1 d . . . . .
H15 H 0.827709 0.627934 0.334543 0.069 Uiso 1 1 calc R U . . .
C2 C 0.68089(15) 0.3207(2) 0.51107(19) 0.0608(8) Uani 1 1 d . . . . .
H2 H 0.711655 0.374392 0.510514 0.073 Uiso 1 1 calc R U . . .
C17 C 0.66031(13) 0.2921(2) 0.59325(17) 0.0526(7) Uani 1 1 d . . . . .
H17 H 0.677092 0.326442 0.647332 0.063 Uiso 1 1 calc R U . . .
C9 C 0.74428(17) 0.6193(3) 0.3847(3) 0.0824(11) Uani 1 1 d . . . . .
H9 H 0.718941 0.625745 0.328490 0.099 Uiso 1 1 calc R U . . .
C19 C 0.72461(16) 0.5884(3) 0.6277(3) 0.0797(11) Uani 1 1 d . . . . .
C5 C 0.71683(15) 0.6075(3) 0.4625(3) 0.0747(10) Uani 1 1 d . . . . .
H5 H 0.672918 0.603982 0.459272 0.090 Uiso 1 1 calc R U . . .
N2 N 0.69938(18) 0.5772(3) 0.6904(3) 0.1197(15) Uani 1 1 d D . . . .
H1WA H 0.618(2) 0.518(3) 0.751(4) 0.20(3) Uiso 1 1 d D . . . .
H1WB H 0.604(5) 0.3962(15) 0.744(8) 0.46(8) Uiso 1 1 d 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
Zn1 O4 1.9434(15) 5_656 ?
Zn1 O4 1.9434(15) 6_556 ?
Zn1 O1 1.9431(16) . ?
Zn1 O1 1.9431(16) 2_656 ?
O4 C10 1.264(3) . ?
N1 C14 1.495(3) . ?
N1 C21 1.333(3) . ?
N1 C3 1.334(3) . ?
O1 C16 1.258(3) . ?
O2 C16 1.232(3) . ?
C1 C4 1.385(3) . ?
C1 C10 1.513(3) . ?
C1 C11 1.384(3) . ?
O3 C10 1.223(3) . ?
C4 H4 0.9300 . ?
C4 C8 1.385(3) . ?
C6 C6 1.480(4) 5_776 ?
C6 C20 1.384(3) . ?
C6 C13 1.384(3) . ?
C8 C16 1.508(3) . ?
C8 C17 1.385(3) . ?
C12 C14 1.496(3) . ?
C12 C18 1.377(3) . ?
C12 C15 1.385(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
O1W H1WA 0.904(18) . ?
O1W H1WB 0.94(2) . ?
C18 H18 0.9300 . ?
C18 C7 1.392(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.363(3) . ?
C21 H21 0.9300 . ?
C11 H11 0.9300 . ?
C11 C2 1.372(4) . ?
C3 H3 0.9300 . ?
C3 C13 1.367(3) . ?
C13 H13 0.9300 . ?
C7 C19 1.435(4) . ?
C7 C5 1.373(5) . ?
C15 H15 0.9300 . ?
C15 C9 1.379(5) . ?
C2 H2 0.9300 . ?
C2 C17 1.384(4) . ?
C17 H17 0.9300 . ?
C9 H9 0.9300 . ?
C9 C5 1.358(5) . ?
C19 N2 1.134(4) . ?
C5 H5 0.9300 . ?

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
O4 Zn1 O4 121.17(10) 5_656 6_556 ?
O1 Zn1 O4 92.89(7) 2_656 6_556 ?
O1 Zn1 O4 92.89(7) . 5_656 ?
O1 Zn1 O4 116.71(8) 2_656 5_656 ?
O1 Zn1 O4 116.71(8) . 6_556 ?
O1 Zn1 O1 118.81(11) . 2_656 ?
C10 O4 Zn1 122.02(14) . 5_656 ?
C21 N1 C14 119.40(17) . . ?
C21 N1 C3 120.37(19) . . ?
C3 N1 C14 120.22(18) . . ?
C16 O1 Zn1 137.19(15) . . ?
C4 C1 C10 119.40(19) . . ?
C11 C1 C4 119.0(2) . . ?
C11 C1 C10 121.58(19) . . ?
C1 C4 H4 119.2 . . ?
C8 C4 C1 121.6(2) . . ?
C8 C4 H4 119.2 . . ?
C20 C6 C6 121.8(2) . 5_776 ?
C13 C6 C6 121.5(2) . 5_776 ?
C13 C6 C20 116.7(2) . . ?
C4 C8 C16 119.2(2) . . ?
C4 C8 C17 118.7(2) . . ?
C17 C8 C16 122.2(2) . . ?
O4 C10 C1 115.35(18) . . ?
O3 C10 O4 124.8(2) . . ?
O3 C10 C1 119.8(2) . . ?
C18 C12 C14 120.4(2) . . ?
C18 C12 C15 119.4(2) . . ?
C15 C12 C14 120.2(2) . . ?
N1 C14 C12 111.57(17) . . ?
N1 C14 H14A 109.3 . . ?
N1 C14 H14B 109.3 . . ?
C12 C14 H14A 109.3 . . ?
C12 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
H1WA O1W H1WB 111(5) . . ?
O1 C16 C8 114.37(19) . . ?
O2 C16 O1 125.3(2) . . ?
O2 C16 C8 120.3(2) . . ?
C12 C18 H18 120.2 . . ?
C12 C18 C7 119.6(2) . . ?
C7 C18 H18 120.2 . . ?
C6 C20 H20 119.6 . . ?
C21 C20 C6 120.8(2) . . ?
C21 C20 H20 119.6 . . ?
N1 C21 C20 120.76(19) . . ?
N1 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C1 C11 H11 120.1 . . ?
C2 C11 C1 119.8(2) . . ?
C2 C11 H11 120.1 . . ?
N1 C3 H3 119.7 . . ?
N1 C3 C13 120.7(2) . . ?
C13 C3 H3 119.7 . . ?
C6 C13 H13 119.7 . . ?
C3 C13 C6 120.7(2) . . ?
C3 C13 H13 119.7 . . ?
C18 C7 C19 120.2(3) . . ?
C5 C7 C18 120.4(3) . . ?
C5 C7 C19 119.4(3) . . ?
C12 C15 H15 119.9 . . ?
C9 C15 C12 120.1(3) . . ?
C9 C15 H15 119.9 . . ?
C11 C2 H2 119.4 . . ?
C11 C2 C17 121.1(2) . . ?
C17 C2 H2 119.4 . . ?
C8 C17 H17 120.1 . . ?
C2 C17 C8 119.8(2) . . ?
C2 C17 H17 120.1 . . ?
C15 C9 H9 119.7 . . ?
C5 C9 C15 120.6(3) . . ?
C5 C9 H9 119.7 . . ?
N2 C19 C7 177.4(5) . . ?
C7 C5 H5 120.1 . . ?
C9 C5 C7 119.8(3) . . ?
C9 C5 H5 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O4 C10 C1 176.88(14) 5_656 . . . ?
Zn1 O4 C10 O3 -2.9(4) 5_656 . . . ?
Zn1 O1 C16 O2 0.5(4) . . . . ?
Zn1 O1 C16 C8 -177.78(18) . . . . ?
N1 C3 C13 C6 -0.6(4) . . . . ?
C1 C4 C8 C16 177.1(2) . . . . ?
C1 C4 C8 C17 -1.6(3) . . . . ?
C1 C11 C2 C17 -0.7(5) . . . . ?
C4 C1 C10 O4 -5.4(3) . . . . ?
C4 C1 C10 O3 174.4(2) . . . . ?
C4 C1 C11 C2 0.0(4) . . . . ?
C4 C8 C16 O1 6.9(3) . . . . ?
C4 C8 C16 O2 -171.5(2) . . . . ?
C4 C8 C17 C2 0.9(4) . . . . ?
C6 C6 C20 C21 179.9(2) 5_776 . . . ?
C6 C6 C13 C3 -179.8(3) 5_776 . . . ?
C6 C20 C21 N1 0.3(4) . . . . ?
C10 C1 C4 C8 -178.1(2) . . . . ?
C10 C1 C11 C2 179.2(3) . . . . ?
C12 C18 C7 C19 179.0(2) . . . . ?
C12 C18 C7 C5 -0.5(4) . . . . ?
C12 C15 C9 C5 -1.7(5) . . . . ?
C14 N1 C21 C20 179.0(2) . . . . ?
C14 N1 C3 C13 -178.8(2) . . . . ?
C14 C12 C18 C7 -179.9(2) . . . . ?
C14 C12 C15 C9 -179.1(3) . . . . ?
C16 C8 C17 C2 -177.7(3) . . . . ?
C18 C12 C14 N1 -91.8(2) . . . . ?
C18 C12 C15 C9 0.6(4) . . . . ?
C18 C7 C5 C9 -0.6(5) . . . . ?
C20 C6 C13 C3 0.8(4) . . . . ?
C21 N1 C14 C12 83.5(2) . . . . ?
C21 N1 C3 C13 0.3(4) . . . . ?
C11 C1 C4 C8 1.1(3) . . . . ?
C11 C1 C10 O4 175.4(2) . . . . ?
C11 C1 C10 O3 -4.8(4) . . . . ?
C11 C2 C17 C8 0.2(5) . . . . ?
C3 N1 C14 C12 -97.4(2) . . . . ?
C3 N1 C21 C20 -0.1(3) . . . . ?
C13 C6 C20 C21 -0.6(4) . . . . ?
C15 C12 C14 N1 87.9(3) . . . . ?
C15 C12 C18 C7 0.4(3) . . . . ?
C15 C9 C5 C7 1.7(6) . . . . ?
C17 C8 C16 O1 -174.5(3) . . . . ?
C17 C8 C16 O2 7.1(4) . . . . ?
C19 C7 C5 C9 179.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
