# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B.
# 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 1845490'
_audit_update_record             
;
2018-05-26 deposited with the CCDC.
2019-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H20 N4 O12 Zn2'
_chemical_formula_weight         759.24

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -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                   24.696(2)
_cell_length_b                   8.3538(6)
_cell_length_c                   16.7962(14)
_cell_angle_alpha                90
_cell_angle_beta                 125.219(2)
_cell_angle_gamma                90
_cell_volume                     2830.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4302
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    1.773
_shelx_estimated_absorpt_T_min   0.729
_shelx_estimated_absorpt_T_max   0.753
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8125
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.639
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             2483
_reflns_number_gt                2138
_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.
 
 _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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0298P)²+7.4340P] 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         2483
_refine_ls_number_parameters     218
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0747
_refine_ls_wR_factor_gt          0.0706
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.035
_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 0.17058(2) 0.72939(4) 0.43349(2) 0.02337(12) Uani 1 1 d . U . . .
O4 O 0.11556(9) 0.2471(2) 0.37574(14) 0.0275(5) Uani 1 1 d . . . . .
O3 O 0.07478(11) 0.8914(3) 0.17067(16) 0.0439(6) Uani 1 1 d . U . . .
O1 O 0.09655(17) 0.8712(3) 0.31528(19) 0.0737(9) Uani 1 1 d . U . . .
O2 O 0.15614(13) 0.7484(4) 0.2852(2) 0.0811(11) Uani 1 1 d . . . . .
C4 C 0.22084(14) 0.2156(3) 0.3640(2) 0.0280(6) Uani 1 1 d . . . . .
H4 H 0.1880 0.1378 0.3402 0.034 Uiso 1 1 calc R U . . .
C6 C 0.26144(13) 0.4796(3) 0.43664(19) 0.0229(6) Uani 1 1 d . . . . .
C2 C 0.32231(14) 0.3039(3) 0.3967(2) 0.0280(7) Uani 1 1 d . . . . .
H2 H 0.3588 0.2878 0.3950 0.034 Uiso 1 1 calc R U . . .
C7 C 0.31636(13) 0.4503(3) 0.43196(19) 0.0237(6) Uani 1 1 d . . . . .
C5 C 0.21187(13) 0.3597(3) 0.39743(19) 0.0230(6) Uani 1 1 d . . . . .
C8 C 0.15229(13) 0.3812(3) 0.39404(19) 0.0238(6) Uani 1 1 d . . . . .
C10 C 0.06729(13) 0.4614(3) 0.3899(2) 0.0263(6) Uani 1 1 d . . . . .
C3 C 0.27600(14) 0.1827(3) 0.3646(2) 0.0285(7) Uani 1 1 d . . . . .
C9 C 0.06167(14) 0.2982(4) 0.3739(2) 0.0290(7) Uani 1 1 d . . . . .
C13 C -0.03817(16) 0.2908(4) 0.3583(2) 0.0399(8) Uani 1 1 d . . . . .
H13 H -0.0744 0.2356 0.3482 0.048 Uiso 1 1 calc R U . . .
C14 C 0.01004(15) 0.2065(4) 0.3586(2) 0.0376(8) Uani 1 1 d . . . . .
H14 H 0.0079 0.0963 0.3492 0.045 Uiso 1 1 calc R U . . .
C1 C 0.28579(16) 0.0235(4) 0.3317(2) 0.0381(8) Uani 1 1 d . . . . .
H1A H 0.2478 -0.0432 0.3086 0.057 Uiso 1 1 calc R U . . .
H1B H 0.3246 -0.0280 0.3856 0.057 Uiso 1 1 calc R U . . .
H1C H 0.2912 0.0406 0.2802 0.057 Uiso 1 1 calc R U . . .
C11 C 0.01830(14) 0.5450(4) 0.3886(2) 0.0342(7) Uani 1 1 d . . . . .
H11 H 0.0206 0.6552 0.3978 0.041 Uiso 1 1 calc R U . . .
C12 C -0.03436(15) 0.4552(5) 0.3727(2) 0.0416(8) Uani 1 1 d . . . . .
H12 H -0.0681 0.5068 0.3717 0.050 Uiso 1 1 calc R U . . .
N1 N 0.12696(10) 0.5100(3) 0.40389(16) 0.0232(5) Uani 1 1 d . . . . .
O5 O 0.25697(9) 0.6112(2) 0.47559(14) 0.0252(4) Uani 1 1 d . . . . .
N2 N 0.10783(14) 0.8379(3) 0.2543(2) 0.0397(7) Uani 1 1 d . U . . .
C15 C 0.36700(14) 0.5671(4) 0.4597(2) 0.0302(7) Uani 1 1 d . . . . .
H15 H 0.3989 0.5394 0.4491 0.036 Uiso 1 1 calc R U . . .
O6 O 0.37305(10) 0.6999(2) 0.49587(16) 0.0336(5) Uani 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 N1 2.037(2) . ?
Zn1 O5 2.0385(18) 7_566 ?
Zn1 O5 2.0705(18) . ?
Zn1 O6 2.096(2) 7_566 ?
Zn1 O1 2.121(3) . ?
Zn1 O2 2.310(3) . ?
O4 C8 1.360(3) . ?
O4 C9 1.381(4) . ?
O3 N2 1.231(3) . ?
O1 N2 1.238(4) . ?
O2 N2 1.240(4) . ?
C4 C3 1.385(4) . ?
C4 C5 1.398(4) . ?
C4 H4 0.9300 . ?
C6 O5 1.316(3) . ?
C6 C5 1.416(4) . ?
C6 C7 1.424(4) . ?
C2 C3 1.383(4) . ?
C2 C7 1.402(4) . ?
C2 H2 0.9300 . ?
C7 C15 1.436(4) . ?
C5 C8 1.450(4) . ?
C8 N1 1.302(4) . ?
C10 C9 1.381(4) . ?
C10 C11 1.386(4) . ?
C10 N1 1.412(3) . ?
C3 C1 1.512(4) . ?
C9 C14 1.379(4) . ?
C13 C14 1.381(5) . ?
C13 C12 1.389(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C11 C12 1.387(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
O5 Zn1 2.0385(18) 7_566 ?
C15 O6 1.232(3) . ?
C15 H15 0.9300 . ?
O6 Zn1 2.096(2) 7_566 ?

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
N1 Zn1 O5 151.99(8) . 7_566 ?
N1 Zn1 O5 87.14(8) . . ?
O5 Zn1 O5 76.66(8) 7_566 . ?
N1 Zn1 O6 91.13(9) . 7_566 ?
O5 Zn1 O6 84.69(8) 7_566 7_566 ?
O5 Zn1 O6 134.92(8) . 7_566 ?
N1 Zn1 O1 102.99(11) . . ?
O5 Zn1 O1 104.29(10) 7_566 . ?
O5 Zn1 O1 138.41(11) . . ?
O6 Zn1 O1 85.73(11) 7_566 . ?
N1 Zn1 O2 93.88(11) . . ?
O5 Zn1 O2 106.61(10) 7_566 . ?
O5 Zn1 O2 83.62(9) . . ?
O6 Zn1 O2 141.38(9) 7_566 . ?
O1 Zn1 O2 55.83(11) . . ?
C8 O4 C9 105.0(2) . . ?
N2 O1 Zn1 99.5(2) . . ?
N2 O2 Zn1 90.3(2) . . ?
C3 C4 C5 123.4(3) . . ?
C3 C4 H4 118.3 . . ?
C5 C4 H4 118.3 . . ?
O5 C6 C5 121.6(2) . . ?
O5 C6 C7 121.8(2) . . ?
C5 C6 C7 116.6(2) . . ?
C3 C2 C7 122.6(3) . . ?
C3 C2 H2 118.7 . . ?
C7 C2 H2 118.7 . . ?
C2 C7 C6 120.5(3) . . ?
C2 C7 C15 116.5(3) . . ?
C6 C7 C15 123.0(3) . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 C8 118.8(2) . . ?
C6 C5 C8 121.1(2) . . ?
N1 C8 O4 113.7(2) . . ?
N1 C8 C5 130.4(2) . . ?
O4 C8 C5 115.9(2) . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 N1 107.1(3) . . ?
C11 C10 N1 132.5(3) . . ?
C2 C3 C4 116.5(3) . . ?
C2 C3 C1 121.1(3) . . ?
C4 C3 C1 122.4(3) . . ?
C14 C9 C10 124.3(3) . . ?
C14 C9 O4 127.4(3) . . ?
C10 C9 O4 108.3(2) . . ?
C14 C13 C12 122.1(3) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C9 C14 C13 114.8(3) . . ?
C9 C14 H14 122.6 . . ?
C13 C14 H14 122.6 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C10 C11 C12 116.3(3) . . ?
C10 C11 H11 121.8 . . ?
C12 C11 H11 121.8 . . ?
C11 C12 C13 122.0(3) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C8 N1 C10 105.8(2) . . ?
C8 N1 Zn1 123.32(18) . . ?
C10 N1 Zn1 130.85(19) . . ?
C6 O5 Zn1 128.99(17) . 7_566 ?
C6 O5 Zn1 126.43(16) . . ?
Zn1 O5 Zn1 103.34(8) 7_566 . ?
O3 N2 O1 123.0(3) . . ?
O3 N2 O2 122.8(3) . . ?
O1 N2 O2 114.2(3) . . ?
O6 C15 C7 127.4(3) . . ?
O6 C15 H15 116.3 . . ?
C7 C15 H15 116.3 . . ?
C15 O6 Zn1 125.28(19) . 7_566 ?

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
C3 C2 C7 C6 0.5(4) . . . . ?
C3 C2 C7 C15 -177.9(3) . . . . ?
O5 C6 C7 C2 175.2(3) . . . . ?
C5 C6 C7 C2 -4.7(4) . . . . ?
O5 C6 C7 C15 -6.5(4) . . . . ?
C5 C6 C7 C15 173.6(3) . . . . ?
C3 C4 C5 C6 -1.7(4) . . . . ?
C3 C4 C5 C8 -179.7(3) . . . . ?
O5 C6 C5 C4 -174.7(2) . . . . ?
C7 C6 C5 C4 5.2(4) . . . . ?
O5 C6 C5 C8 3.3(4) . . . . ?
C7 C6 C5 C8 -176.8(2) . . . . ?
C9 O4 C8 N1 0.1(3) . . . . ?
C9 O4 C8 C5 -178.6(2) . . . . ?
C4 C5 C8 N1 -166.3(3) . . . . ?
C6 C5 C8 N1 15.7(5) . . . . ?
C4 C5 C8 O4 12.1(4) . . . . ?
C6 C5 C8 O4 -165.8(2) . . . . ?
C7 C2 C3 C4 3.2(4) . . . . ?
C7 C2 C3 C1 -177.0(3) . . . . ?
C5 C4 C3 C2 -2.6(4) . . . . ?
C5 C4 C3 C1 177.6(3) . . . . ?
C11 C10 C9 C14 -1.9(5) . . . . ?
N1 C10 C9 C14 179.0(3) . . . . ?
C11 C10 C9 O4 177.9(3) . . . . ?
N1 C10 C9 O4 -1.2(3) . . . . ?
C8 O4 C9 C14 -179.5(3) . . . . ?
C8 O4 C9 C10 0.7(3) . . . . ?
C10 C9 C14 C13 1.3(5) . . . . ?
O4 C9 C14 C13 -178.5(3) . . . . ?
C12 C13 C14 C9 -0.2(5) . . . . ?
C9 C10 C11 C12 1.4(4) . . . . ?
N1 C10 C11 C12 -179.8(3) . . . . ?
C10 C11 C12 C13 -0.4(5) . . . . ?
C14 C13 C12 C11 -0.2(5) . . . . ?
O4 C8 N1 C10 -0.8(3) . . . . ?
C5 C8 N1 C10 177.7(3) . . . . ?
O4 C8 N1 Zn1 179.16(16) . . . . ?
C5 C8 N1 Zn1 -2.3(4) . . . . ?
C9 C10 N1 C8 1.2(3) . . . . ?
C11 C10 N1 C8 -177.7(3) . . . . ?
C9 C10 N1 Zn1 -178.75(19) . . . . ?
C11 C10 N1 Zn1 2.3(5) . . . . ?
C5 C6 O5 Zn1 162.28(19) . . . 7_566 ?
C7 C6 O5 Zn1 -17.6(4) . . . 7_566 ?
C5 C6 O5 Zn1 -32.6(4) . . . . ?
C7 C6 O5 Zn1 147.5(2) . . . . ?
Zn1 O1 N2 O3 178.1(2) . . . . ?
Zn1 O1 N2 O2 -3.2(3) . . . . ?
Zn1 O2 N2 O3 -178.4(3) . . . . ?
Zn1 O2 N2 O1 2.9(3) . . . . ?
C2 C7 C15 O6 -176.8(3) . . . . ?
C6 C7 C15 O6 4.9(5) . . . . ?
C7 C15 O6 Zn1 19.5(4) . . . 7_566 ?

_refine_diff_density_max         0.721
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.064

_shelxl_version_number           2014-3

