# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 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_ZJU_QCD_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1943053'
loop_
_audit_author_name
_audit_author_address
'Jun Zhang'
;Zhejiang University
China
;
_audit_update_record             
;
2019-07-25 deposited with the CCDC.	2021-07-02 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         ?
_chemical_formula_sum            'C16 H12 N2 O9 Zn2'
_chemical_formula_weight         507.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -2.7473 0.5279 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   32.9307(17)
_cell_length_b                   5.3798(3)
_cell_length_c                   9.1492(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.282(2)
_cell_angle_gamma                90
_cell_volume                     1611.14(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5664
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      63.46

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.090
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.795
_shelx_estimated_absorpt_T_min   0.605
_shelx_estimated_absorpt_T_max   0.605
_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      173(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8 VENTURE PHOTON II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6987
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.349
_diffrn_reflns_theta_max         63.551
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_point_group_measured_fraction_full 0.951
_reflns_number_total             3468
_reflns_number_gt                3343
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_max     0.783
_reflns_Friedel_fraction_full    0.910

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0611P)²+2.5251P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.41(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3468
_refine_ls_number_parameters     273
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1095
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
Zn2 Zn 0.74479(3) 0.24917(15) 0.74888(8) 0.0119(2) Uani 1 1 d . . . . .
N1 N 0.69659(13) 0.5017(9) 0.8055(5) 0.0128(9) Uani 1 1 d . . . . .
H1A H 0.705505 0.587483 0.888536 0.015 Uiso 1 1 calc R U . . .
H1B H 0.690619 0.613189 0.731418 0.015 Uiso 1 1 calc R U . . .
C1 C 0.54924(17) 0.3582(11) 0.6810(6) 0.0153(11) Uani 1 1 d . . . . .
O1 O 0.51558(12) 0.3639(8) 0.7390(4) 0.0202(8) Uani 1 1 d . . . . .
N2 N 0.29434(15) 0.4955(10) 0.1923(6) 0.0170(10) Uani 1 1 d . . . . .
H2A H 0.285985 0.579604 0.108076 0.020 Uiso 1 1 calc R U . . .
H2AB H 0.300276 0.608854 0.265379 0.020 Uiso 1 1 calc R U . . .
C2 C 0.58867(18) 0.2889(12) 0.7702(6) 0.0150(11) Uani 1 1 d . . . . .
O2 O 0.55068(12) 0.4165(8) 0.5491(5) 0.0224(9) Uani 1 1 d . . . . .
O3 O 0.70138(12) -0.0162(8) 1.1314(4) 0.0154(8) Uani 1 1 d . . . . .
C3 C 0.58979(17) 0.0934(12) 0.8685(7) 0.0182(11) Uani 1 1 d . . . . .
H3 H 0.565665 0.004207 0.883026 0.022 Uiso 1 1 calc R U . . .
O5 O 0.47181(12) 0.1716(10) 0.3165(4) 0.0252(9) Uani 1 1 d . . . . .
C5 C 0.66277(16) 0.1629(11) 0.9246(6) 0.0132(10) Uani 1 1 d . . . . .
O4 O 0.73456(11) 0.0699(7) 0.9389(4) 0.0123(8) Uani 1 1 d . . . . .
C4 C 0.62719(17) 0.0305(12) 0.9456(6) 0.0190(12) Uani 1 1 d . . . . .
H4 H 0.628615 -0.103920 1.013365 0.023 Uiso 1 1 calc R U . . .
O6 O 0.44395(14) 0.5024(10) 0.4053(5) 0.0289(10) Uani 1 1 d . . . . .
C6 C 0.70252(16) 0.0664(10) 1.0033(6) 0.0108(10) Uani 1 1 d . . . . .
C8 C 0.44154(17) 0.3167(14) 0.3237(6) 0.0191(12) Uani 1 1 d . . . . .
O8 O 0.28899(12) -0.0214(8) -0.1306(4) 0.0167(8) Uani 1 1 d . . . . .
C7 C 0.62322(16) 0.4254(11) 0.7494(6) 0.0133(10) Uani 1 1 d . . . . .
H7 H 0.621448 0.559863 0.681762 0.016 Uiso 1 1 calc R U . . .
O7 O 0.25496(11) 0.0711(7) 0.0596(4) 0.0120(7) Uani 1 1 d . . . . .
C9 C 0.40170(18) 0.2579(11) 0.2383(7) 0.0167(13) Uani 1 1 d . . . . .
O9 O 0.50227(14) 0.8925(8) 0.5510(5) 0.0232(9) Uani 1 1 d . . . . .
H9A H 0.499878 0.946735 0.637863 0.035 Uiso 1 1 d R U . A .
H9B H 0.494378 1.026735 0.503763 0.035 Uiso 1 1 d R U . . .
C00G C 0.66083(16) 0.3649(10) 0.8284(5) 0.0110(10) Uani 1 1 d . . . . .
C10 C 0.39811(17) 0.0536(14) 0.1471(7) 0.0232(14) Uani 1 1 d . . . . .
H10 H 0.420914 -0.052665 0.141278 0.028 Uiso 1 1 calc R U . . .
C11 C 0.36120(17) 0.0025(12) 0.0635(7) 0.0194(12) Uani 1 1 d . . . . .
H11 H 0.359372 -0.132981 -0.003461 0.023 Uiso 1 1 calc R U . . .
C12 C 0.32683(16) 0.1488(11) 0.0772(6) 0.0132(10) Uani 1 1 d . . . . .
C13 C 0.33025(15) 0.3547(11) 0.1726(6) 0.0128(11) Uani 1 1 d . . . . .
C14 C 0.36772(17) 0.4110(11) 0.2499(6) 0.0145(10) Uani 1 1 d . . . . .
H14 H 0.370387 0.554074 0.311015 0.017 Uiso 1 1 calc R U . . .
C15 C 0.28694(16) 0.0646(10) -0.0039(6) 0.0104(10) Uani 1 1 d . . . . .
Zn1 Zn 0.50310(3) 0.57317(18) 0.44332(9) 0.0132(3) Uani 0.869(4) 1 d . . P A 1
Zn1A Zn 0.48677(19) 0.5767(12) 0.5603(7) 0.014(2) Uani 0.131(4) 1 d . . P A 2


_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
Zn2 O7 2.043(4) 4 ?
Zn2 O4 2.048(4) . ?
Zn2 O3 2.105(4) 2_554 ?
Zn2 O8 2.123(4) 3_556 ?
Zn2 N1 2.194(5) . ?
Zn2 N2 2.202(5) 4 ?
N1 C00G 1.423(7) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
C1 O2 1.253(7) . ?
C1 O1 1.280(7) . ?
C1 C2 1.503(8) . ?
C1 Zn1A 2.517(8) . ?
O1 Zn1 1.986(4) 2_565 ?
O1 Zn1A 2.132(8) . ?
N2 C13 1.432(7) . ?
N2 H2A 0.9100 . ?
N2 H2AB 0.9100 . ?
C2 C3 1.381(9) . ?
C2 C7 1.385(8) . ?
O2 Zn1 1.942(4) . ?
O2 Zn1A 2.287(8) . ?
O3 C6 1.258(6) . ?
C3 C4 1.393(8) . ?
C3 H3 0.9500 . ?
O5 C8 1.273(8) . ?
C5 C00G 1.396(8) . ?
C5 C4 1.402(8) . ?
C5 C6 1.515(7) . ?
O4 C6 1.263(6) . ?
C4 H4 0.9500 . ?
O6 C8 1.244(8) . ?
O6 Zn1A 1.929(7) . ?
O6 Zn1 1.978(5) . ?
C8 C9 1.486(7) . ?
C8 Zn1 2.593(6) . ?
O8 C15 1.256(7) . ?
C7 C00G 1.402(7) . ?
C7 H7 0.9500 . ?
O7 C15 1.258(6) . ?
C9 C10 1.377(9) . ?
C9 C14 1.402(8) . ?
O9 Zn1A 1.779(8) . ?
O9 Zn1 1.982(4) . ?
O9 H9A 0.8583 . ?
O9 H9B 0.8667 . ?
C10 C11 1.391(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.395(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.407(8) . ?
C12 C15 1.506(7) . ?
C13 C14 1.387(7) . ?
C14 H14 0.9500 . ?
Zn1A H9A 2.1416 . ?

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
O7 Zn2 O4 179.8(2) 4 . ?
O7 Zn2 O3 90.81(16) 4 2_554 ?
O4 Zn2 O3 89.28(16) . 2_554 ?
O7 Zn2 O8 89.92(16) 4 3_556 ?
O4 Zn2 O8 89.99(16) . 3_556 ?
O3 Zn2 O8 179.0(2) 2_554 3_556 ?
O7 Zn2 N1 95.56(16) 4 . ?
O4 Zn2 N1 84.31(17) . . ?
O3 Zn2 N1 91.18(17) 2_554 . ?
O8 Zn2 N1 89.42(16) 3_556 . ?
O7 Zn2 N2 83.64(18) 4 4 ?
O4 Zn2 N2 96.48(17) . 4 ?
O3 Zn2 N2 90.20(18) 2_554 4 ?
O8 Zn2 N2 89.21(18) 3_556 4 ?
N1 Zn2 N2 178.4(2) . 4 ?
C00G N1 Zn2 110.3(3) . . ?
C00G N1 H1A 109.6 . . ?
Zn2 N1 H1A 109.6 . . ?
C00G N1 H1B 109.6 . . ?
Zn2 N1 H1B 109.6 . . ?
H1A N1 H1B 108.1 . . ?
O2 C1 O1 121.3(5) . . ?
O2 C1 C2 117.6(5) . . ?
O1 C1 C2 121.1(5) . . ?
O2 C1 Zn1A 64.9(3) . . ?
O1 C1 Zn1A 57.9(3) . . ?
C2 C1 Zn1A 166.0(5) . . ?
C1 O1 Zn1 132.2(4) . 2_565 ?
C1 O1 Zn1A 91.6(4) . . ?
C13 N2 Zn2 110.9(4) . 4_454 ?
C13 N2 H2A 109.5 . . ?
Zn2 N2 H2A 109.5 4_454 . ?
C13 N2 H2AB 109.5 . . ?
Zn2 N2 H2AB 109.5 4_454 . ?
H2A N2 H2AB 108.0 . . ?
C3 C2 C7 121.9(6) . . ?
C3 C2 C1 120.2(5) . . ?
C7 C2 C1 117.9(5) . . ?
C1 O2 Zn1 118.4(4) . . ?
C1 O2 Zn1A 85.4(4) . . ?
C6 O3 Zn2 126.7(3) . 2 ?
C2 C3 C4 118.3(5) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C00G C5 C4 120.1(5) . . ?
C00G C5 C6 122.9(5) . . ?
C4 C5 C6 116.9(5) . . ?
C6 O4 Zn2 128.8(4) . . ?
C3 C4 C5 120.8(5) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C8 O6 Zn1A 126.9(5) . . ?
C8 O6 Zn1 104.9(4) . . ?
O3 C6 O4 123.4(5) . . ?
O3 C6 C5 116.8(4) . . ?
O4 C6 C5 119.7(5) . . ?
O6 C8 O5 121.6(5) . . ?
O6 C8 C9 118.7(6) . . ?
O5 C8 C9 119.6(6) . . ?
O6 C8 Zn1 47.5(3) . . ?
O5 C8 Zn1 76.6(3) . . ?
C9 C8 Zn1 160.0(5) . . ?
C15 O8 Zn2 126.2(4) . 3_444 ?
C2 C7 C00G 120.0(5) . . ?
C2 C7 H7 120.0 . . ?
C00G C7 H7 120.0 . . ?
C15 O7 Zn2 128.9(4) . 4_454 ?
C10 C9 C14 119.9(5) . . ?
C10 C9 C8 120.0(6) . . ?
C14 C9 C8 120.1(5) . . ?
Zn1A O9 H9A 103.0 . . ?
Zn1 O9 H9A 139.7 . . ?
Zn1A O9 H9B 138.4 . . ?
Zn1 O9 H9B 119.6 . . ?
H9A O9 H9B 97.2 . . ?
C5 C00G C7 118.8(5) . . ?
C5 C00G N1 120.9(5) . . ?
C7 C00G N1 120.2(5) . . ?
C9 C10 C11 120.2(6) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 120.5(6) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 119.3(5) . . ?
C11 C12 C15 117.3(5) . . ?
C13 C12 C15 123.3(5) . . ?
C14 C13 C12 119.6(5) . . ?
C14 C13 N2 121.4(5) . . ?
C12 C13 N2 118.9(5) . . ?
C13 C14 C9 120.4(5) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
O8 C15 O7 124.6(5) . . ?
O8 C15 C12 115.7(5) . . ?
O7 C15 C12 119.6(5) . . ?
O2 Zn1 O6 136.8(2) . . ?
O2 Zn1 O9 100.55(19) . . ?
O6 Zn1 O9 100.8(2) . . ?
O2 Zn1 O1 107.71(18) . 2_564 ?
O6 Zn1 O1 99.70(19) . 2_564 ?
O9 Zn1 O1 109.60(18) . 2_564 ?
O2 Zn1 C8 122.0(2) . . ?
O6 Zn1 C8 27.6(2) . . ?
O9 Zn1 C8 128.2(2) . . ?
O1 Zn1 C8 85.78(18) 2_564 . ?
O9 Zn1A O6 110.7(4) . . ?
O9 Zn1A O1 116.3(4) . . ?
O6 Zn1A O1 132.9(4) . . ?
O9 Zn1A O2 95.0(4) . . ?
O6 Zn1A O2 119.4(4) . . ?
O1 Zn1A O2 59.8(2) . . ?
O9 Zn1A C1 104.0(3) . . ?
O6 Zn1A C1 136.2(4) . . ?
O1 Zn1A C1 30.56(19) . . ?
O2 Zn1A C1 29.74(19) . . ?
O9 Zn1A H9A 23.0 . . ?
O6 Zn1A H9A 122.7 . . ?
O1 Zn1A H9A 100.9 . . ?
O2 Zn1A H9A 102.2 . . ?
C1 Zn1A H9A 99.4 . . ?

_refine_diff_density_max         1.089
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.104

