# 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. 
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data_xb9884_0m_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1900699'
loop_
_audit_author_name
_audit_author_address
zzzlelezzz
;Northwest University
China
;
_audit_update_record             
;
2019-11-21 deposited with the CCDC.	2020-07-20 downloaded from the CCDC.
;
_audit_creation_date             2018-04-23
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H16 N6 O6 Zn'
_chemical_formula_sum            'C24 H16 N6 O6 Zn'
_chemical_formula_weight         549.80
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.0291(19)
_cell_length_b                   8.3132(10)
_cell_length_c                   17.158(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.520(2)
_cell_angle_gamma                90
_cell_volume                     2285.5(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3592
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.13
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.130
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0636 before and 0.0420 after correction. The Ratio of minimum to maximum transmission is 0.8924. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic whiteish colourless'
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12356
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.783
_diffrn_reflns_theta_min         2.375
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3819
_reflns_number_total             4807
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4807
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0348
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0445P)²+0.3940P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0911
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), N11(H11), C14(H14), C17(H17), C18(H18), C22(H22), C23(H23), C28(H28),
 C31(H31), C32(H32), C33(H33), C34(H34), C35(H35)
2.b Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.80059(2) 0.15173(3) 0.23047(2) 0.02983(10) Uani 1 1 d . . . . .
O5 O 0.89552(10) 0.0094(2) 0.19965(10) 0.0405(4) Uani 1 1 d . . . . .
N1 N 0.69453(11) 0.0416(2) 0.26095(11) 0.0331(4) Uani 1 1 d . . . . .
N3 N 0.76875(12) 0.3682(2) 0.18926(12) 0.0348(5) Uani 1 1 d . . . . .
O3 O 1.02453(12) 0.1170(2) 0.66178(10) 0.0476(5) Uani 1 1 d . . . . .
H3 H 1.0443 0.1000 0.7056 0.071 Uiso 1 1 calc GR . . . .
O1 O 0.84947(10) 0.2273(2) 0.32957(9) 0.0381(4) Uani 1 1 d . . . . .
C4 C 0.78006(17) 0.5084(3) 0.22515(15) 0.0430(6) Uani 1 1 d . . . . .
H4 H 0.8162 0.5248 0.2677 0.052 Uiso 1 1 calc R . . . .
N5 N 0.36800(13) -0.3470(3) 0.48151(13) 0.0425(5) Uani 1 1 d . . . . .
N2 N 0.68904(12) -0.0014(3) 0.33619(12) 0.0336(5) Uani 1 1 d . . . . .
C9 C 0.42707(14) -0.3318(3) 0.53762(14) 0.0326(5) Uani 1 1 d . . . . .
O2 O 0.82128(11) 0.0777(2) 0.43280(10) 0.0485(5) Uani 1 1 d . . . . .
N11 N 0.71195(12) 0.3979(2) 0.13129(11) 0.0341(5) Uani 1 1 d . . . . .
H11 H 0.6936 0.3265 0.0988 0.041 Uiso 1 1 calc R . . . .
C12 C 0.61377(14) -0.0610(3) 0.35194(14) 0.0329(5) Uani 1 1 d . . . . .
C13 C 0.86518(14) 0.1742(3) 0.39743(14) 0.0312(5) Uani 1 1 d . . . . .
C14 C 0.99693(14) 0.3283(3) 0.39063(13) 0.0307(5) Uani 1 1 d . . . . .
H14 H 0.9807 0.3550 0.3398 0.037 Uiso 1 1 calc R . . . .
C15 C 0.94442(14) 0.2350(3) 0.43549(13) 0.0293(5) Uani 1 1 d . . . . .
C16 C 1.04494(14) 0.2501(3) 0.54241(13) 0.0326(5) Uani 1 1 d . . . . .
C17 C 1.09666(15) 0.3425(3) 0.49662(14) 0.0342(5) Uani 1 1 d . . . . .
H17 H 1.1476 0.3785 0.5171 0.041 Uiso 1 1 calc R . . . .
C18 C 0.52261(14) -0.1986(3) 0.44672(14) 0.0333(5) Uani 1 1 d . . . . .
H18 H 0.4866 -0.2283 0.4058 0.040 Uiso 1 1 calc R . . . .
C19 C 0.50401(14) -0.2424(3) 0.52243(13) 0.0307(5) Uani 1 1 d . . . . .
O4 O 1.14097(13) 0.2609(3) 0.65033(11) 0.0625(6) Uani 1 1 d . . . . .
C21 C 0.59428(14) -0.1108(3) 0.43108(14) 0.0324(5) Uani 1 1 d . . . . .
C22 C 0.56819(16) -0.0570(4) 0.28273(14) 0.0440(6) Uani 1 1 d . . . . .
H22 H 0.5134 -0.0909 0.2744 0.053 Uiso 1 1 calc R . . . .
C23 C 0.55876(14) -0.1990(3) 0.58332(14) 0.0328(5) Uani 1 1 d . . . . .
H23 H 0.5474 -0.2295 0.6341 0.039 Uiso 1 1 calc R . . . .
C24 C 0.87213(15) -0.0190(3) 0.12957(14) 0.0348(5) Uani 1 1 d . . . . .
C25 C 1.07558(17) 0.2124(3) 0.62301(14) 0.0401(6) Uani 1 1 d . . . . .
O6 O 0.80535(11) 0.0385(2) 0.10394(10) 0.0498(5) Uani 1 1 d . . . . .
N6 N 0.30801(14) -0.4364(3) 0.51471(14) 0.0485(6) Uani 1 1 d . . . . .
C28 C 0.40310(17) -0.4090(4) 0.60514(16) 0.0499(7) Uani 1 1 d . . . . .
H28 H 0.4329 -0.4146 0.6523 0.060 Uiso 1 1 calc R . . . .
C29 C 1.07311(14) 0.3818(3) 0.42065(14) 0.0324(5) Uani 1 1 d . . . . .
C30 C 0.63020(14) -0.1104(3) 0.56857(13) 0.0318(5) Uani 1 1 d . . . . .
C31 C 0.96834(14) 0.1963(3) 0.51145(13) 0.0304(5) Uani 1 1 d . . . . .
H31 H 0.9334 0.1345 0.5418 0.037 Uiso 1 1 calc R . . . .
C32 C 0.64774(14) -0.0673(3) 0.49295(14) 0.0342(5) Uani 1 1 d . . . . .
H32 H 0.6957 -0.0085 0.4832 0.041 Uiso 1 1 calc R . . . .
C33 C 0.62061(15) 0.0075(3) 0.22840(15) 0.0408(6) Uani 1 1 d . . . . .
H33 H 0.6061 0.0247 0.1762 0.049 Uiso 1 1 calc R . . . .
C34 C 0.32677(18) -0.4751(4) 0.58814(17) 0.0535(8) Uani 1 1 d . . . . .
H34 H 0.2943 -0.5353 0.6215 0.064 Uiso 1 1 calc R . . . .
C35 C 0.73101(18) 0.6264(3) 0.19081(16) 0.0455(7) Uani 1 1 d . . . . .
H35 H 0.7279 0.7339 0.2054 0.055 Uiso 1 1 calc R . . . .
C36 C 0.68781(14) 0.5526(3) 0.13070(13) 0.0324(5) Uani 1 1 d . . . . .
H6 H 0.264(2) -0.456(4) 0.4822(19) 0.074(10) Uiso 1 1 d . . . . .
H2 H 0.7301(18) 0.015(3) 0.3692(17) 0.058(9) Uiso 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
Zn1 O5 2.0094(16) . ?
Zn1 N1 2.0120(19) . ?
Zn1 N3 1.9946(19) . ?
Zn1 O1 1.9568(16) . ?
Zn1 O6 2.3692(18) . ?
O5 C24 1.272(3) . ?
N1 N2 1.345(3) . ?
N1 C33 1.327(3) . ?
N3 C4 1.328(3) . ?
N3 N11 1.353(3) . ?
O3 C25 1.330(3) . ?
O1 C13 1.264(3) . ?
C4 C35 1.380(3) . ?
N5 C9 1.338(3) . ?
N5 N6 1.353(3) . ?
N2 C12 1.338(3) . ?
C9 C19 1.469(3) . ?
C9 C28 1.388(3) . ?
O2 C13 1.237(3) . ?
N11 C36 1.343(3) . ?
C12 C21 1.461(3) . ?
C12 C22 1.378(3) . ?
C13 C15 1.500(3) . ?
C14 C15 1.392(3) . ?
C14 C29 1.386(3) . ?
C15 C31 1.387(3) . ?
C16 C17 1.389(3) . ?
C16 C25 1.489(3) . ?
C16 C31 1.398(3) . ?
C17 C29 1.386(3) . ?
C18 C19 1.389(3) . ?
C18 C21 1.393(3) . ?
C19 C23 1.394(3) . ?
O4 C25 1.206(3) . ?
C21 C32 1.394(3) . ?
C22 C33 1.380(3) . ?
C23 C30 1.390(3) . ?
C24 O6 1.242(3) . ?
C24 C29 1.495(3) 2_745 ?
N6 C34 1.327(3) . ?
C28 C34 1.365(4) . ?
C29 C24 1.495(3) 2_755 ?
C30 C32 1.382(3) . ?
C30 C36 1.472(3) 4_566 ?
C35 C36 1.372(3) . ?
C36 C30 1.472(3) 4_565 ?

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 116.84(8) . . ?
O5 Zn1 O6 58.80(6) . . ?
N1 Zn1 O6 96.06(7) . . ?
N3 Zn1 O5 128.78(8) . . ?
N3 Zn1 N1 107.00(8) . . ?
N3 Zn1 O6 92.73(7) . . ?
O1 Zn1 O5 97.43(7) . . ?
O1 Zn1 N1 103.99(7) . . ?
O1 Zn1 N3 96.38(8) . . ?
O1 Zn1 O6 154.41(7) . . ?
C24 O5 Zn1 98.72(14) . . ?
N2 N1 Zn1 116.61(14) . . ?
C33 N1 Zn1 137.64(17) . . ?
C33 N1 N2 105.47(19) . . ?
C4 N3 Zn1 126.63(17) . . ?
C4 N3 N11 105.15(19) . . ?
N11 N3 Zn1 125.88(15) . . ?
C13 O1 Zn1 138.90(16) . . ?
N3 C4 C35 110.9(2) . . ?
C9 N5 N6 104.3(2) . . ?
C12 N2 N1 112.00(19) . . ?
N5 C9 C19 120.1(2) . . ?
N5 C9 C28 110.5(2) . . ?
C28 C9 C19 129.4(2) . . ?
C36 N11 N3 111.62(19) . . ?
N2 C12 C21 120.6(2) . . ?
N2 C12 C22 106.1(2) . . ?
C22 C12 C21 133.3(2) . . ?
O1 C13 C15 115.4(2) . . ?
O2 C13 O1 125.2(2) . . ?
O2 C13 C15 119.4(2) . . ?
C29 C14 C15 120.9(2) . . ?
C14 C15 C13 117.7(2) . . ?
C31 C15 C13 122.7(2) . . ?
C31 C15 C14 119.5(2) . . ?
C17 C16 C25 117.1(2) . . ?
C17 C16 C31 119.6(2) . . ?
C31 C16 C25 123.4(2) . . ?
C29 C17 C16 120.7(2) . . ?
C19 C18 C21 121.1(2) . . ?
C18 C19 C9 120.0(2) . . ?
C18 C19 C23 119.1(2) . . ?
C23 C19 C9 120.8(2) . . ?
C18 C21 C12 121.7(2) . . ?
C18 C21 C32 118.9(2) . . ?
C32 C21 C12 119.4(2) . . ?
C12 C22 C33 105.8(2) . . ?
C30 C23 C19 120.4(2) . . ?
O5 C24 C29 119.0(2) . 2_745 ?
O6 C24 O5 119.5(2) . . ?
O6 C24 C29 121.5(2) . 2_745 ?
O3 C25 C16 113.4(2) . . ?
O4 C25 O3 123.0(2) . . ?
O4 C25 C16 123.5(2) . . ?
C24 O6 Zn1 82.93(15) . . ?
C34 N6 N5 112.8(2) . . ?
C34 C28 C9 105.9(2) . . ?
C14 C29 C17 119.3(2) . . ?
C14 C29 C24 119.2(2) . 2_755 ?
C17 C29 C24 121.5(2) . 2_755 ?
C23 C30 C36 123.0(2) . 4_566 ?
C32 C30 C23 119.8(2) . . ?
C32 C30 C36 117.1(2) . 4_566 ?
C15 C31 C16 120.1(2) . . ?
C30 C32 C21 120.7(2) . . ?
N1 C33 C22 110.6(2) . . ?
N6 C34 C28 106.5(2) . . ?
C36 C35 C4 105.9(2) . . ?
N11 C36 C30 119.5(2) . 4_565 ?
N11 C36 C35 106.4(2) . . ?
C35 C36 C30 133.9(2) . 4_565 ?

_olex2_submission_special_instructions 'No special instructions were received'
