# 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_sq
_database_code_depnum_ccdc_archive 'CCDC 1810642'
loop_
_audit_author_name
_audit_author_address
'Pengyan Wu'
;Jiangsu Normal University
China
;
_audit_update_record             
;
2019-07-05 deposited with the CCDC.	2019-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H10 N2 O7 Zn1.5, 2(C3 H7 N O), 3[C3H7NO]'
_chemical_formula_sum            'C33 H45 N7 O12 Zn1.50'
_chemical_formula_weight         829.81

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   5.9994(12)
_cell_length_b                   29.661(6)
_cell_length_c                   19.068(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.09
_cell_angle_gamma                90
_cell_volume                     3393.0(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3377
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      22.55

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_F_000             1732
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.146
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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 area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19162
_diffrn_reflns_av_unetI/netI     0.2190
_diffrn_reflns_av_R_equivalents  0.1398
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.740
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.940
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 0.940
_reflns_number_total             5607
_reflns_number_gt                2116
_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-2018/3 (Sheldrick, 2018)'
_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)+(0.0075P)²] 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         5607
_refine_ls_number_parameters     349
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.1747
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1262
_refine_ls_wR_factor_gt          0.1152
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.042
_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
Zn1 Zn 1.000000 0.500000 0.500000 0.0327(3) Uani 1 2 d S . P . .
Zn2 Zn 0.50583(12) 0.45101(2) 0.50392(4) 0.0376(2) Uani 1 1 d . . . . .
O1W O 0.6852(5) 0.50188(12) 0.54103(18) 0.0338(10) Uani 1 1 d . . . . .
O6 O 1.3659(8) 0.58616(15) 0.5668(2) 0.0556(14) Uani 1 1 d . . . . .
O4 O 1.6385(9) 0.91200(14) 0.9295(3) 0.0604(15) Uani 1 1 d . . . . .
O5 O 1.0787(7) 0.54091(16) 0.5881(2) 0.0615(15) Uani 1 1 d . . . . .
C14 C 1.1365(12) 0.6020(2) 0.6648(4) 0.0504(19) Uani 1 1 d . . . . .
O3 O 1.9715(8) 0.94185(14) 0.9362(2) 0.0627(15) Uani 1 1 d . . . . .
C8 C 2.1347(13) 0.8817(2) 0.8350(4) 0.055(2) Uani 1 1 d . . . . .
H8A H 2.226261 0.905721 0.847300 0.066 Uiso 1 1 calc R U . . .
C4 C 1.5829(16) 0.7532(2) 0.8291(4) 0.063(2) Uani 1 1 d . . . . .
C18 C 1.1946(13) 0.5738(2) 0.6013(4) 0.0419(19) Uani 1 1 d . . . . .
C1 C 1.4190(15) 0.7189(2) 0.8168(4) 0.074(2) Uani 1 1 d . . . . .
C6 C 1.7874(11) 0.8418(2) 0.8497(3) 0.0417(18) Uani 1 1 d . . . . .
H6A H 1.645195 0.839407 0.868677 0.050 Uiso 1 1 calc R U . . .
C5 C 1.8745(14) 0.8092(2) 0.8047(4) 0.057(2) Uani 1 1 d . U . . .
N1 N 1.7409(11) 0.7722(2) 0.7886(3) 0.0672(19) Uani 1 1 d . . . . .
H1A H 1.761755 0.760063 0.748130 0.081 Uiso 1 1 calc R U . . .
C11 C 1.8449(13) 0.9148(2) 0.9147(3) 0.0383(18) Uani 1 1 d . . . . .
C2 C 1.3309(19) 0.7211(3) 0.8880(5) 0.112(3) Uani 1 1 d . U . . .
C15 C 0.9425(14) 0.5952(3) 0.7021(4) 0.073(2) Uani 1 1 d . . . . .
H15A H 0.841283 0.573502 0.687101 0.087 Uiso 1 1 calc R U . . .
C7 C 1.9271(12) 0.8785(2) 0.8647(3) 0.0436(18) Uani 1 1 d . . . . .
C13 C 1.2788(11) 0.6359(2) 0.6848(4) 0.056(2) Uani 1 1 d . . . . .
H13A H 1.405599 0.641493 0.658115 0.067 Uiso 1 1 calc R U . . .
C12 C 1.2391(15) 0.6618(3) 0.7428(4) 0.069(2) Uani 1 1 d . U . . .
O2 O 1.1810(14) 0.7033(2) 0.9206(3) 0.138(3) Uani 1 1 d . U . . .
N2 N 1.3964(10) 0.69608(18) 0.7559(3) 0.073(2) Uani 1 1 d . . . . .
H2A H 1.485581 0.703033 0.722354 0.088 Uiso 1 1 calc R U . . .
C16 C 0.8951(14) 0.6211(3) 0.7633(5) 0.090(3) Uani 1 1 d . . . . .
H16A H 0.770411 0.615448 0.790833 0.107 Uiso 1 1 calc R U . . .
C17 C 1.0461(15) 0.6556(3) 0.7798(4) 0.080(2) Uani 1 1 d . U . . .
H17A H 1.014257 0.674802 0.816961 0.096 Uiso 1 1 calc R U . . .
O8 O 0.6097(11) 0.4995(2) 0.6842(3) 0.103(2) Uani 1 1 d D . . . .
C24 C 0.4263(16) 0.4909(3) 0.7027(5) 0.092(3) Uani 1 1 d D . . . .
H24A H 0.326439 0.482579 0.667666 0.110 Uiso 1 1 calc R U . . .
O1 O 1.5512(11) 0.77735(18) 0.9547(3) 0.112(2) Uani 1 1 d . . . . .
N4 N 0.3448(15) 0.4917(4) 0.7685(5) 0.161(4) Uani 1 1 d D . . . .
O7 O 1.7361(13) 0.7770(2) 1.1624(3) 0.117(3) Uani 1 1 d D . . . .
N3 N 1.9701(13) 0.7922(2) 1.0730(4) 0.085(2) Uani 1 1 d D . . . .
C20 C 2.0378(14) 0.8169(3) 1.0103(4) 0.106(3) Uani 1 1 d D . . . .
H20A H 2.180026 0.806087 0.994669 0.160 Uiso 1 1 calc R U . . .
H20B H 1.929088 0.812523 0.973922 0.160 Uiso 1 1 calc R U . . .
H20C H 2.048588 0.848485 1.021059 0.160 Uiso 1 1 calc R U . . .
C21 C 1.7777(17) 0.7981(4) 1.1103(5) 0.129(5) Uani 1 1 d D . . . .
H21A H 1.675085 0.819367 1.094710 0.154 Uiso 1 1 calc R U . . .
C19 C 2.1332(17) 0.7529(4) 1.0893(5) 0.165(5) Uani 1 1 d D . . . .
H19A H 2.257702 0.754303 1.057834 0.248 Uiso 1 1 calc R U . . .
H19B H 2.185242 0.755446 1.136772 0.248 Uiso 1 1 calc R U . . .
H19C H 2.057363 0.724641 1.083379 0.248 Uiso 1 1 calc R U . . .
C9 C 2.2117(12) 0.8504(3) 0.7874(4) 0.072(2) Uani 1 1 d . . . . .
H9A H 2.348254 0.853882 0.765007 0.087 Uiso 1 1 calc R U . . .
C3 C 1.4977(16) 0.7561(3) 0.9037(4) 0.080(3) Uani 1 1 d . . . . .
C10 C 2.0758(14) 0.8134(3) 0.7744(4) 0.070(2) Uani 1 1 d . U . . .
H10A H 2.125052 0.791059 0.743947 0.084 Uiso 1 1 calc R U . . .
C23 C 0.455(2) 0.5203(6) 0.8298(8) 0.368(14) Uani 1 1 d D . . . .
H23A H 0.370908 0.516164 0.872201 0.552 Uiso 1 1 calc R U . . .
H23B H 0.605382 0.510450 0.837128 0.552 Uiso 1 1 calc R U . . .
H23C H 0.454383 0.551674 0.817299 0.552 Uiso 1 1 calc R U . . .
C22 C 0.1012(18) 0.4771(4) 0.7871(7) 0.205(6) Uani 1 1 d D . . . .
H22A H 0.077928 0.480302 0.836635 0.308 Uiso 1 1 calc R U . . .
H22B H -0.002608 0.495895 0.762239 0.308 Uiso 1 1 calc R U . . .
H22C H 0.078992 0.446232 0.773780 0.308 Uiso 1 1 calc R U . . .


_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 O1W 2.046(3) . ?
Zn1 O1W 2.046(3) 3_766 ?
Zn1 O3 2.118(4) 4_475 ?
Zn1 O3 2.118(4) 2_846 ?
Zn1 O5 2.125(4) . ?
Zn1 O5 2.125(4) 3_766 ?
Zn2 O6 1.905(5) 3_766 ?
Zn2 O4 1.925(5) 2_746 ?
Zn2 O1W 1.983(3) . ?
Zn2 O1W 1.999(3) 3_666 ?
Zn2 Zn2 2.9108(14) 3_666 ?
O6 C18 1.275(8) . ?
O4 C11 1.273(7) . ?
O5 C18 1.224(7) . ?
C14 C13 1.375(8) . ?
C14 C15 1.380(9) . ?
C14 C18 1.511(9) . ?
O3 C11 1.177(7) . ?
C8 C7 1.373(9) . ?
C8 C9 1.378(8) . ?
C4 N1 1.348(9) . ?
C4 C1 1.433(10) . ?
C4 C3 1.515(11) . ?
C1 N2 1.351(8) . ?
C1 C2 1.458(12) . ?
C6 C5 1.396(9) . ?
C6 C7 1.401(8) . ?
C5 C10 1.345(10) . ?
C5 N1 1.394(8) . ?
C11 C7 1.522(9) . ?
C2 O2 1.214(10) . ?
C2 C3 1.473(11) . ?
C15 C16 1.427(10) . ?
C13 C12 1.369(9) . ?
C12 C17 1.368(11) . ?
C12 N2 1.409(8) . ?
C16 C17 1.401(9) . ?
O8 C24 1.184(7) . ?
C24 N4 1.347(9) . ?
O1 C3 1.202(8) . ?
N4 C22 1.565(11) . ?
N4 C23 1.588(11) . ?
O7 C21 1.201(8) . ?
N3 C21 1.368(9) . ?
N3 C20 1.462(8) . ?
N3 C19 1.552(9) . ?
C9 C10 1.388(8) . ?

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
O1W Zn1 O1W 180.0 . 3_766 ?
O1W Zn1 O3 97.11(16) . 4_475 ?
O1W Zn1 O3 82.89(16) 3_766 4_475 ?
O1W Zn1 O3 82.89(17) . 2_846 ?
O1W Zn1 O3 97.11(16) 3_766 2_846 ?
O3 Zn1 O3 180.00(13) 4_475 2_846 ?
O1W Zn1 O5 83.47(16) . . ?
O1W Zn1 O5 96.53(16) 3_766 . ?
O3 Zn1 O5 90.41(19) 4_475 . ?
O3 Zn1 O5 89.59(19) 2_846 . ?
O1W Zn1 O5 96.53(16) . 3_766 ?
O1W Zn1 O5 83.47(16) 3_766 3_766 ?
O3 Zn1 O5 89.59(19) 4_475 3_766 ?
O3 Zn1 O5 90.41(19) 2_846 3_766 ?
O5 Zn1 O5 180.0 . 3_766 ?
O6 Zn2 O4 107.6(2) 3_766 2_746 ?
O6 Zn2 O1W 118.26(18) 3_766 . ?
O4 Zn2 O1W 117.80(18) 2_746 . ?
O6 Zn2 O1W 109.44(18) 3_766 3_666 ?
O4 Zn2 O1W 116.41(18) 2_746 3_666 ?
O1W Zn2 O1W 86.07(12) . 3_666 ?
O6 Zn2 Zn2 123.45(16) 3_766 3_666 ?
O4 Zn2 Zn2 128.55(16) 2_746 3_666 ?
O1W Zn2 Zn2 43.26(10) . 3_666 ?
O1W Zn2 Zn2 42.82(9) 3_666 3_666 ?
Zn2 O1W Zn2 93.93(12) . 3_666 ?
Zn2 O1W Zn1 110.09(17) . . ?
Zn2 O1W Zn1 112.57(17) 3_666 . ?
C18 O6 Zn2 121.7(5) . 3_766 ?
C11 O4 Zn2 123.0(4) . 2_756 ?
C18 O5 Zn1 138.0(5) . . ?
C13 C14 C15 119.1(7) . . ?
C13 C14 C18 118.9(7) . . ?
C15 C14 C18 121.9(7) . . ?
C11 O3 Zn1 143.6(5) . 2_856 ?
C7 C8 C9 122.0(7) . . ?
N1 C4 C1 133.3(7) . . ?
N1 C4 C3 138.9(7) . . ?
C1 C4 C3 87.8(8) . . ?
O5 C18 O6 125.5(7) . . ?
O5 C18 C14 118.3(8) . . ?
O6 C18 C14 116.2(7) . . ?
N2 C1 C4 124.3(8) . . ?
N2 C1 C2 141.8(9) . . ?
C4 C1 C2 93.8(7) . . ?
C5 C6 C7 116.0(7) . . ?
C10 C5 N1 119.7(7) . . ?
C10 C5 C6 122.5(7) . . ?
N1 C5 C6 117.8(8) . . ?
C4 N1 C5 127.4(6) . . ?
O3 C11 O4 126.6(7) . . ?
O3 C11 C7 119.3(7) . . ?
O4 C11 C7 114.1(7) . . ?
O2 C2 C1 136.6(9) . . ?
O2 C2 C3 134.9(8) . . ?
C1 C2 C3 88.5(8) . . ?
C14 C15 C16 120.9(7) . . ?
C8 C7 C6 120.8(6) . . ?
C8 C7 C11 120.3(7) . . ?
C6 C7 C11 118.9(7) . . ?
C12 C13 C14 121.8(8) . . ?
C17 C12 C13 119.3(7) . . ?
C17 C12 N2 125.0(7) . . ?
C13 C12 N2 115.5(8) . . ?
C1 N2 C12 125.5(7) . . ?
C17 C16 C15 116.5(8) . . ?
C12 C17 C16 122.0(8) . . ?
O8 C24 N4 127.8(9) . . ?
C24 N4 C22 123.1(8) . . ?
C24 N4 C23 123.0(9) . . ?
C22 N4 C23 111.6(8) . . ?
C21 N3 C20 126.6(8) . . ?
C21 N3 C19 121.7(8) . . ?
C20 N3 C19 111.4(8) . . ?
O7 C21 N3 122.6(10) . . ?
C8 C9 C10 116.9(8) . . ?
O1 C3 C2 135.6(8) . . ?
O1 C3 C4 134.4(9) . . ?
C2 C3 C4 89.9(7) . . ?
C5 C10 C9 121.6(7) . . ?

_refine_diff_density_max         0.784
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.084

_smtbx_masks_special_details     
;
A solvent mask was calculated and 478 electrons were
found in a volume of 988Å^3 in 1 void per unit cell.
This is consistent with the presence of 3[C3H7NO]
per Formula Unit which account for 480 electrons
per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.461 0.000 0.500 494.3 239.5 '6 DMF'
2 -0.802 0.500 1.000 494.3 239.5 '6 DMF'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2



