# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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 1834633'
loop_
_audit_author_name
_audit_author_address
'Xiao nan Li'
;Northeast Normal University
China
;
_audit_update_record             
;
2018-04-04 deposited with the CCDC.	2019-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 N O8 Zn'
_chemical_formula_weight         415.67

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1    '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5023(4)
_cell_length_b                   9.5077(5)
_cell_length_c                   10.6017(6)
_cell_angle_alpha                68.918(2)
_cell_angle_beta                 66.791(2)
_cell_angle_gamma                86.570(2)
_cell_volume                     817.62(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    8629
_cell_measurement_theta_min      2.306
_cell_measurement_theta_max      27.082

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             426
_exptl_absorpt_coefficient_mu    1.549
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.635
_exptl_absorpt_correction_T_max  0.679
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14332
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         27.16
_reflns_number_total             3587
_reflns_number_gt                3190
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0633P)²+0.1094P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3587
_refine_ls_number_parameters     247
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.1080
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.279
_refine_ls_restrained_S_all      1.278
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.88494(3) 0.13391(3) 0.40713(3) 0.02287(12) Uani 1 1 d . . .
O1 O 0.68107(18) 0.19844(19) 0.4339(2) 0.0281(4) Uani 1 1 d . . .
O2 O 0.17110(19) 0.07689(18) 0.4525(2) 0.0299(4) Uani 1 1 d . . .
O3 O 0.00114(19) 0.2480(2) 0.4665(2) 0.0315(4) Uani 1 1 d . . .
O4 O 1.0304(2) 0.1647(2) 0.2075(2) 0.0334(4) Uani 1 1 d . . .
O5 O 0.8549(2) 0.0711(2) 0.1611(2) 0.0408(5) Uani 1 1 d . . .
N1 N 0.8410(2) 0.3244(2) -0.0964(2) 0.0255(4) Uani 1 1 d . . .
O6 O 0.7948(2) 0.4186(2) 0.2581(3) 0.0483(6) Uani 1 1 d . . .
C1 C 0.1330(2) 0.2058(2) 0.4527(2) 0.0207(4) Uani 1 1 d . . .
C2 C 0.2551(2) 0.3187(2) 0.4243(2) 0.0194(4) Uani 1 1 d . . .
C3 C 0.9744(3) 0.1480(3) 0.1206(3) 0.0255(5) Uani 1 1 d . . .
C4 C 1.0698(3) 0.2334(3) -0.0415(3) 0.0294(5) Uani 1 1 d . . .
H4A H 1.1605 0.1812 -0.0728 0.035 Uiso 1 1 calc R . .
H4B H 1.1042 0.3335 -0.0542 0.035 Uiso 1 1 calc R . .
C5 C 0.5221(2) 0.3819(3) 0.3634(2) 0.0214(4) Uani 1 1 d . . .
C6 C 0.4939(3) 0.5324(3) 0.3406(3) 0.0251(5) Uani 1 1 d . . .
H6 H 0.5744 0.6049 0.3085 0.030 Uiso 1 1 calc R . .
C7 C 0.5721(3) 0.4627(3) -0.0187(2) 0.0222(4) Uani 1 1 d . . .
C8 C 0.4024(2) 0.2755(2) 0.4048(2) 0.0205(4) Uani 1 1 d . . .
H8 H 0.4210 0.1749 0.4196 0.025 Uiso 1 1 calc R . .
C9 C 0.2267(3) 0.4685(3) 0.4074(3) 0.0226(4) Uani 1 1 d . . .
H9 H 0.1277 0.4972 0.4240 0.027 Uiso 1 1 calc R . .
C10 C 0.7041(3) 0.2442(3) -0.0420(3) 0.0318(5) Uani 1 1 d . . .
H10 H 0.7007 0.1427 -0.0310 0.038 Uiso 1 1 calc R . .
C11 C 0.9853(3) 0.2501(3) -0.1409(3) 0.0325(5) Uani 1 1 d . . .
H11A H 1.0522 0.3097 -0.2419 0.039 Uiso 1 1 calc R . .
H11B H 0.9607 0.1508 -0.1373 0.039 Uiso 1 1 calc R . .
C12 C 0.6790(3) 0.3330(3) 0.3468(3) 0.0249(5) Uani 1 1 d . . .
C13 C 0.7158(3) 0.5412(3) -0.0729(3) 0.0262(5) Uani 1 1 d . . .
H13 H 0.7220 0.6422 -0.0829 0.031 Uiso 1 1 calc R . .
C14 C 0.8483(3) 0.4710(3) -0.1118(3) 0.0276(5) Uani 1 1 d . . .
H14 H 0.9434 0.5249 -0.1488 0.033 Uiso 1 1 calc R . .
C15 C 0.3460(3) 0.5748(3) 0.3657(3) 0.0254(5) Uani 1 1 d . . .
H15 H 0.3268 0.6747 0.3546 0.030 Uiso 1 1 calc R . .
C16 C 0.5701(3) 0.3109(3) -0.0029(3) 0.0318(6) Uani 1 1 d . . .
H16 H 0.4764 0.2541 0.0347 0.038 Uiso 1 1 calc R . .
O1W O 0.3191(3) 0.0133(3) 0.1524(3) 0.0590(6) Uani 1 1 d D . .
O2W O 0.5458(3) 0.9371(4) 0.2725(3) 0.0678(8) Uani 1 1 d D . .
H2WA H 0.495(5) 0.899(6) 0.3648(14) 0.102 Uiso 1 1 d D . .
H2WB H 0.630(3) 0.976(6) 0.260(5) 0.102 Uiso 1 1 d D . .
H1WA H 0.250(4) 0.037(6) 0.219(4) 0.102 Uiso 1 1 d D . .
H1WB H 0.389(4) -0.016(6) 0.185(5) 0.102 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 O1 1.9389(16) . ?
Zn1 O4 1.9420(19) . ?
Zn1 O2 1.9679(16) 2_656 ?
Zn1 O3 1.9931(17) 1_655 ?
O1 C12 1.285(3) . ?
O2 C1 1.258(3) . ?
O2 Zn1 1.9679(16) 2_656 ?
O3 C1 1.261(3) . ?
O3 Zn1 1.9931(17) 1_455 ?
O4 C3 1.289(3) . ?
O5 C3 1.224(3) . ?
N1 C14 1.346(3) . ?
N1 C10 1.348(3) . ?
N1 C11 1.489(3) . ?
O6 C12 1.224(3) . ?
C1 C2 1.493(3) . ?
C2 C8 1.391(3) . ?
C2 C9 1.393(3) . ?
C3 C4 1.514(3) . ?
C4 C11 1.520(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C8 1.391(3) . ?
C5 C6 1.391(3) . ?
C5 C12 1.497(3) . ?
C6 C15 1.386(3) . ?
C6 H6 0.9300 . ?
C7 C16 1.392(3) . ?
C7 C13 1.396(3) . ?
C7 C7 1.482(5) 2_665 ?
C8 H8 0.9300 . ?
C9 C15 1.386(3) . ?
C9 H9 0.9300 . ?
C10 C16 1.369(4) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 C14 1.374(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
O1W H1WA 0.844(10) . ?
O1W H1WB 0.851(10) . ?
O2W H2WA 0.845(10) . ?
O2W H2WB 0.845(10) . ?

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 Zn1 O4 117.67(8) . . ?
O1 Zn1 O2 99.58(7) . 2_656 ?
O4 Zn1 O2 116.58(8) . 2_656 ?
O1 Zn1 O3 112.64(7) . 1_655 ?
O4 Zn1 O3 100.66(8) . 1_655 ?
O2 Zn1 O3 110.13(8) 2_656 1_655 ?
C12 O1 Zn1 114.70(15) . . ?
C1 O2 Zn1 137.16(16) . 2_656 ?
C1 O3 Zn1 113.73(15) . 1_455 ?
C3 O4 Zn1 116.38(16) . . ?
C14 N1 C10 120.7(2) . . ?
C14 N1 C11 119.8(2) . . ?
C10 N1 C11 119.5(2) . . ?
O2 C1 O3 124.0(2) . . ?
O2 C1 C2 117.58(19) . . ?
O3 C1 C2 118.3(2) . . ?
C8 C2 C9 119.5(2) . . ?
C8 C2 C1 119.11(19) . . ?
C9 C2 C1 121.20(19) . . ?
O5 C3 O4 124.8(2) . . ?
O5 C3 C4 121.1(2) . . ?
O4 C3 C4 114.2(2) . . ?
C3 C4 C11 114.2(2) . . ?
C3 C4 H4A 108.7 . . ?
C11 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C11 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C8 C5 C6 119.6(2) . . ?
C8 C5 C12 119.8(2) . . ?
C6 C5 C12 120.6(2) . . ?
C15 C6 C5 120.2(2) . . ?
C15 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C16 C7 C13 117.0(2) . . ?
C16 C7 C7 121.3(2) . 2_665 ?
C13 C7 C7 121.7(3) . 2_665 ?
C5 C8 C2 120.4(2) . . ?
C5 C8 H8 119.8 . . ?
C2 C8 H8 119.8 . . ?
C15 C9 C2 120.1(2) . . ?
C15 C9 H9 120.0 . . ?
C2 C9 H9 120.0 . . ?
N1 C10 C16 120.5(2) . . ?
N1 C10 H10 119.7 . . ?
C16 C10 H10 119.7 . . ?
N1 C11 C4 112.0(2) . . ?
N1 C11 H11A 109.2 . . ?
C4 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
C4 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
O6 C12 O1 123.8(2) . . ?
O6 C12 C5 121.1(2) . . ?
O1 C12 C5 115.06(19) . . ?
C14 C13 C7 120.7(2) . . ?
C14 C13 H13 119.7 . . ?
C7 C13 H13 119.7 . . ?
N1 C14 C13 120.3(2) . . ?
N1 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C9 C15 C6 120.1(2) . . ?
C9 C15 H15 119.9 . . ?
C6 C15 H15 119.9 . . ?
C10 C16 C7 120.8(2) . . ?
C10 C16 H16 119.6 . . ?
C7 C16 H16 119.6 . . ?
H1WA O1W H1WB 104(2) . . ?
H2WA O2W H2WB 106(2) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.16
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.634
_refine_diff_density_min         -1.082
_refine_diff_density_rms         0.237
