# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_h111628_0m
_database_code_depnum_ccdc_archive 'CCDC 2089942'
loop_
_audit_author_name
_audit_author_address
'He liancheng'
;Yunnan university
China
;
_audit_update_record             
;
2021-06-15 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_audit_creation_date             2021-04-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H24 N4 O10 Zn2, H2 O'
_chemical_formula_sum            'C28 H26 N4 O11 Zn2'
_chemical_formula_weight         725.27
_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 0.0030 0.0020 '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 0.0110 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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.9486(9)
_cell_length_b                   12.9217(15)
_cell_length_c                   13.9630(17)
_cell_angle_alpha                90
_cell_angle_beta                 90.085(6)
_cell_angle_gamma                90
_cell_volume                     1434.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3509
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.742
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6320
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             740
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13943
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.467
_diffrn_reflns_theta_min         2.147
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2162
_reflns_number_total             2885
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.809
_refine_diff_density_min         -0.968
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2885
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.087
_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)+(0.0802P)²+2.4808P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1599
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: O6(0.5) H6a(0.5) H6b(0.5)
3.a Riding coordinates:
 O5(H5a,H5b), N2(H2a,H2b)
3.b Free rotating group:
 O6(H6a,H6b)
3.c Secondary CH2 refined with riding coordinates:
 N1(H1a,H1b)
3.d Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C3(H3), C11(H11), C14(H14), 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 0.26596(7) 0.46312(4) 0.44293(4) 0.0170(2) Uani 1 1 d . . . . .
O5 O 0.2457(4) 0.5049(3) 0.5791(2) 0.0197(8) Uani 1 1 d . . . . .
H5A H 0.329583 0.542788 0.594582 0.030 Uiso 1 1 d R U . A 2
H5B H 0.244903 0.471118 0.625322 0.030 Uiso 1 1 d R U . A 2
O1 O 0.4728(4) 0.3823(3) 0.4185(2) 0.0211(8) Uani 1 1 d . . . . .
O3 O 0.3288(4) 0.5910(3) 0.3742(2) 0.0223(8) Uani 1 1 d . . . . .
O4 O 0.0913(5) 0.6645(3) 0.4254(3) 0.0291(9) Uani 1 1 d . . . . .
O2 O 0.3518(5) 0.2505(3) 0.4958(3) 0.0276(9) Uani 1 1 d . . . . .
N1 N 0.0712(5) 0.3818(3) 0.3868(3) 0.0193(9) Uani 1 1 d . . . . .
H1A H 0.065421 0.319658 0.414216 0.023 Uiso 1 1 calc R U . B 1
H1B H -0.025118 0.414829 0.397734 0.023 Uiso 1 1 calc R U . B 1
N2 N 0.8224(5) 0.1551(4) 0.1903(3) 0.0243(10) Uani 1 1 d . . . . .
H2A H 0.929438 0.156806 0.174360 0.029 Uiso 1 1 d R U . . .
H2B H 0.779968 0.210326 0.163920 0.029 Uiso 1 1 d R U . . .
C8 C 0.1667(6) 0.2805(4) 0.2486(3) 0.0187(11) Uani 1 1 d . . . . .
H8 H 0.190935 0.225585 0.289366 0.022 Uiso 1 1 calc R U . . .
C9 C 0.2004(6) 0.2719(4) 0.1505(3) 0.0177(11) Uani 1 1 d . . . . .
C2 C 0.6158(6) 0.2193(4) 0.4214(3) 0.0179(11) Uani 1 1 d . . . . .
C7 C 0.0975(6) 0.3707(4) 0.2851(3) 0.0176(10) Uani 1 1 d . . . . .
C10 C 0.1621(6) 0.3551(4) 0.0889(3) 0.0194(11) Uani 1 1 d . . . . .
C1 C 0.4709(6) 0.2863(4) 0.4493(3) 0.0187(11) Uani 1 1 d . . . . .
C6 C 0.2301(6) 0.6695(4) 0.3865(3) 0.0205(11) Uani 1 1 d . . . . .
C13 C 0.1974(7) 0.3504(4) -0.0158(3) 0.0225(11) Uani 1 1 d . . . . .
C12 C 0.0610(6) 0.4546(4) 0.2260(4) 0.0223(11) Uani 1 1 d . . . . .
H12 H 0.015701 0.514993 0.251333 0.027 Uiso 1 1 calc R U . . .
C3 C 0.6613(6) 0.2231(4) 0.3250(3) 0.0207(11) Uani 1 1 d . . . . .
H3 H 0.609295 0.270340 0.284294 0.025 Uiso 1 1 calc R U . . .
C4 C 0.7843(6) 0.1567(4) 0.2894(3) 0.0215(11) Uani 1 1 d . . . . .
C11 C 0.0938(7) 0.4464(4) 0.1278(4) 0.0249(12) Uani 1 1 d . . . . .
H11 H 0.070093 0.502070 0.087702 0.030 Uiso 1 1 calc R U . . .
C14 C 0.3206(7) 0.4155(5) -0.0535(4) 0.0253(12) Uani 1 1 d . . . . .
H14 H 0.375362 0.461482 -0.012848 0.030 Uiso 1 1 calc R U . . .
C5 C 0.8640(7) 0.0860(5) 0.3507(4) 0.0264(12) Uani 1 1 d . . . . .
H5 H 0.945011 0.040738 0.327261 0.032 Uiso 1 1 calc R U . . .
O6 O 0.6087(11) 0.3429(6) 0.1140(6) 0.036(2) Uani 0.5 1 d G . P . .
H6A H 0.675051 0.343653 0.066302 0.053 Uiso 0.5 1 d G U P . .
H6B H 0.542680 0.291752 0.102949 0.053 Uiso 0.5 1 d G U P . .


_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 O5 1.983(3) . ?
Zn1 O1 1.978(3) . ?
Zn1 O3 1.975(3) . ?
Zn1 N1 2.028(4) . ?
O5 H5A 0.8544 . ?
O5 H5B 0.7796 . ?
O1 C1 1.314(6) . ?
O3 C6 1.295(6) . ?
O4 C6 1.232(6) . ?
O2 C1 1.239(6) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C7 1.444(6) . ?
N2 H2A 0.8803 . ?
N2 H2B 0.8712 . ?
N2 C4 1.417(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.401(6) . ?
C8 C7 1.386(7) . ?
C9 C10 1.409(7) . ?
C9 C6 1.524(7) 2_545 ?
C2 C1 1.493(7) . ?
C2 C13 1.414(7) 4_666 ?
C2 C3 1.395(6) . ?
C7 C12 1.392(7) . ?
C10 C13 1.490(6) . ?
C10 C11 1.409(7) . ?
C13 C14 1.395(7) . ?
C12 H12 0.9300 . ?
C12 C11 1.400(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.394(7) . ?
C4 C5 1.403(8) . ?
C11 H11 0.9300 . ?
C14 H14 0.9300 . ?
C14 C5 1.381(7) 4_565 ?
C5 H5 0.9300 . ?
O6 H6A 0.8498 . ?
O6 H6B 0.8580 . ?

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
O5 Zn1 N1 116.65(15) . . ?
O1 Zn1 O5 112.19(14) . . ?
O1 Zn1 N1 107.11(16) . . ?
O3 Zn1 O5 105.00(15) . . ?
O3 Zn1 O1 98.43(14) . . ?
O3 Zn1 N1 116.08(16) . . ?
Zn1 O5 H5A 109.5 . . ?
Zn1 O5 H5B 129.9 . . ?
H5A O5 H5B 96.8 . . ?
C1 O1 Zn1 115.6(3) . . ?
C6 O3 Zn1 116.0(3) . . ?
Zn1 N1 H1A 110.0 . . ?
Zn1 N1 H1B 110.0 . . ?
H1A N1 H1B 108.3 . . ?
C7 N1 Zn1 108.7(3) . . ?
C7 N1 H1A 110.0 . . ?
C7 N1 H1B 110.0 . . ?
H2A N2 H2B 104.2 . . ?
C4 N2 H2A 117.0 . . ?
C4 N2 H2B 108.5 . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.2(5) . . ?
C8 C9 C10 119.6(5) . . ?
C8 C9 C6 118.1(4) . 2_545 ?
C10 C9 C6 122.2(4) . 2_545 ?
C13 C2 C1 124.1(4) 4_666 . ?
C3 C2 C1 115.6(4) . . ?
C3 C2 C13 120.2(5) . 4_666 ?
C8 C7 N1 120.2(4) . . ?
C8 C7 C12 121.3(4) . . ?
C12 C7 N1 118.4(4) . . ?
C9 C10 C13 121.8(4) . . ?
C11 C10 C9 119.2(4) . . ?
C11 C10 C13 119.0(5) . . ?
O1 C1 C2 117.0(4) . . ?
O2 C1 O1 122.2(5) . . ?
O2 C1 C2 120.7(5) . . ?
O3 C6 C9 114.6(4) . 2 ?
O4 C6 O3 124.1(5) . . ?
O4 C6 C9 121.4(5) . 2 ?
C2 C13 C10 123.2(4) 4_565 . ?
C14 C13 C2 118.1(4) . 4_565 ?
C14 C13 C10 118.7(5) . . ?
C7 C12 H12 120.6 . . ?
C7 C12 C11 118.9(5) . . ?
C11 C12 H12 120.6 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(5) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 N2 120.6(5) . . ?
C3 C4 C5 120.0(4) . . ?
C5 C4 N2 119.3(5) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.8(5) . . ?
C12 C11 H11 119.6 . . ?
C13 C14 H14 118.9 . . ?
C5 C14 C13 122.3(5) 4_565 . ?
C5 C14 H14 118.9 4_565 . ?
C4 C5 H5 120.4 . . ?
C14 C5 C4 119.1(5) 4_666 . ?
C14 C5 H5 120.4 4_666 . ?
H6A O6 H6B 104.4 . . ?

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 O1 C1 O2 -4.4(6) . . . . ?
Zn1 O1 C1 C2 172.5(3) . . . . ?
Zn1 O3 C6 O4 -11.1(7) . . . . ?
Zn1 O3 C6 C9 168.3(3) . . . 2 ?
Zn1 N1 C7 C8 98.0(5) . . . . ?
Zn1 N1 C7 C12 -78.3(5) . . . . ?
N1 C7 C12 C11 176.9(4) . . . . ?
N2 C4 C5 C14 -176.9(5) . . . 4_666 ?
C8 C9 C10 C13 179.2(5) . . . . ?
C8 C9 C10 C11 1.4(7) . . . . ?
C8 C7 C12 C11 0.7(8) . . . . ?
C9 C8 C7 N1 -176.6(4) . . . . ?
C9 C8 C7 C12 -0.5(7) . . . . ?
C9 C10 C13 C2 65.3(7) . . . 4_565 ?
C9 C10 C13 C14 -112.6(6) . . . . ?
C9 C10 C11 C12 -1.2(8) . . . . ?
C2 C13 C14 C5 0.2(9) 4_565 . . 4_565 ?
C2 C3 C4 N2 175.4(5) . . . . ?
C2 C3 C4 C5 -0.5(8) . . . . ?
C7 C8 C9 C10 -0.6(7) . . . . ?
C7 C8 C9 C6 -177.5(4) . . . 2_545 ?
C7 C12 C11 C10 0.1(8) . . . . ?
C10 C13 C14 C5 178.2(5) . . . 4_565 ?
C1 C2 C3 C4 -174.0(5) . . . . ?
C6 C9 C10 C13 -3.9(7) 2_545 . . . ?
C6 C9 C10 C11 178.2(5) 2_545 . . . ?
C13 C2 C1 O1 137.6(5) 4_666 . . . ?
C13 C2 C1 O2 -45.4(7) 4_666 . . . ?
C13 C2 C3 C4 1.6(8) 4_666 . . . ?
C13 C10 C11 C12 -179.1(5) . . . . ?
C3 C2 C1 O1 -47.0(6) . . . . ?
C3 C2 C1 O2 130.0(5) . . . . ?
C3 C4 C5 C14 -0.9(8) . . . 4_666 ?
C11 C10 C13 C2 -116.8(6) . . . 4_565 ?
C11 C10 C13 C14 65.3(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
