# Supplementary Information (SI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_GZ4-135a_a_sq
_audit_block_doi                 10.5517/ccdc.csd.cc2k7qcx
_database_code_depnum_ccdc_archive 'CCDC 2360909'
loop_
_audit_author_name
_audit_author_address
'Simon J. Teat'
;Advanced Light Source Lawrence Berkeley National Laboratory
United States of America
;
_audit_update_record             
;
2024-06-05 deposited with the CCDC.	2024-10-30 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            'C19 H14 N O4 Zn'
_chemical_formula_weight         385.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
H H 0.0000 0.0000
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
N N 0.0065 0.0035
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
O O 0.0115 0.0064
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'
Zn Zn 0.2768 1.5030
'XDISP Program in WinGX S.Brennan & P.L.Cowan Rev.Sci.Instrum.63,850 1992'

_space_group_crystal_system      tetragonal
_space_group_IT_number           140
_space_group_name_H-M_alt        'I 4/m c m'
_space_group_name_Hall           '-I 4 2c'

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

_cell_length_a                   15.3499(10)
_cell_length_b                   15.3499(10)
_cell_length_c                   19.0385(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4485.8(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9981
_cell_measurement_theta_min      2.9186
_cell_measurement_theta_max      34.2348

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_F_000             1576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.189
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            59973
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.721
_diffrn_reflns_theta_max         34.248
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2324
_reflns_number_gt                1989
_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       'Bruker APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.40a'
_computing_data_reduction        'Bruker SAINT v8.40a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_refine_special_details          
;
 All non-hydrogen atoms were refined anisotropically. Hydrogen
 atoms were placed geometrically on the carbon atoms constrained
 and refined using a riding model. 
 Once the refinement converged SQUEEZE was used to remove the electron
 density in the void region. SQUEEZE reported Solvent Accessible
 Volume of 1627 Ang3 and Electrons Found in S.A.V. to be 338. As this
 was a mixed solvent system no addition solvent was added to the formula
 based on the SQUEEZE output. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0384P)²+4.7558P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2324
_refine_ls_number_parameters     80
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0857
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_restrained_S_all      1.154
_refine_ls_shift/su_max          0.001
_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 0.500000 0.500000 0.17418(2) 0.01258(8) Uani 1 4 d S T P . .
O1 O 0.60690(5) 0.57460(5) 0.19406(4) 0.01804(15) Uani 1 1 d . . . . .
C1 C 0.61689(7) 0.61689(7) 0.250000 0.0160(2) Uani 1 2 d S T P . .
C2 C 0.68578(7) 0.68578(7) 0.250000 0.0171(3) Uani 1 2 d S T P . .
C3 C 0.76555(7) 0.66870(7) 0.28244(7) 0.0223(2) Uani 1 1 d . . . . .
C4 C 0.78382(10) 0.58711(9) 0.31543(10) 0.0380(4) Uani 1 1 d . . . . .
H4A H 0.740653 0.542761 0.315914 0.046 Uiso 1 1 calc R U . . .
C5 C 0.86237(12) 0.57237(12) 0.34612(15) 0.0613(7) Uani 1 1 d . . . . .
H5A H 0.873633 0.517769 0.367788 0.074 Uiso 1 1 calc R U . . .
N1 N 0.500000 0.500000 0.06732(10) 0.0154(3) Uani 1 4 d S T P . .
C6 C 0.5891(6) 0.516(2) 0.0403(3) 0.0271(13) Uani 0.25 1 d . . P . .
H6A H 0.628996 0.470331 0.057723 0.033 Uiso 0.25 1 calc R U P . .
H6B H 0.610353 0.573092 0.057724 0.033 Uiso 0.25 1 calc R U P . .
C7 C 0.472(3) 0.4142(8) 0.0402(3) 0.0269(14) Uani 0.25 1 d . . P . .
H7A H 0.412481 0.400961 0.057616 0.032 Uiso 0.25 1 calc R U P . .
H7B H 0.511687 0.368350 0.057616 0.032 Uiso 0.25 1 calc R U P . .
C8 C 0.442(2) 0.5686(17) 0.0403(3) 0.0275(13) Uani 0.25 1 d . . P . .
H8A H 0.461648 0.626103 0.057744 0.033 Uiso 0.25 1 calc R U P . .
H8B H 0.381948 0.558623 0.057745 0.033 Uiso 0.25 1 calc R U P . .


_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 2.0344(19) . ?
Zn1 O1 2.0364(8) 2_665 ?
Zn1 O1 2.0364(8) 3_655 ?
Zn1 O1 2.0364(8) 4_565 ?
Zn1 O1 2.0364(8) . ?
Zn1 Zn1 2.8871(5) 5_655 ?
O1 C1 1.2567(10) . ?
C1 C2 1.496(2) . ?
C2 C3 1.3962(13) 7 ?
C2 C3 1.3962(13) . ?
C3 C3 1.427(2) 31_665 ?
C3 C4 1.4289(18) . ?
C4 C5 1.359(2) . ?
C4 H4A 0.9500 . ?
C5 C5 1.417(3) 31_665 ?
C5 H5A 0.9500 . ?
N1 C8 1.473(6) . ?
N1 C7 1.479(6) . ?
N1 C6 1.482(6) . ?
C6 C6 1.534(12) 18 ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 H7B 0.735(19) 3_655 ?
C6 H8A 0.741(18) 4_565 ?
C7 C7 1.531(11) 18 ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 H8B 0.76(2) 3_655 ?
C8 C8 1.536(10) 18 ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?

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 O1 100.71(2) . 2_665 ?
N1 Zn1 O1 100.71(2) . 3_655 ?
O1 Zn1 O1 88.021(9) 2_665 3_655 ?
N1 Zn1 O1 100.71(2) . 4_565 ?
O1 Zn1 O1 88.021(9) 2_665 4_565 ?
O1 Zn1 O1 158.58(5) 3_655 4_565 ?
N1 Zn1 O1 100.71(2) . . ?
O1 Zn1 O1 158.58(5) 2_665 . ?
O1 Zn1 O1 88.020(9) 3_655 . ?
O1 Zn1 O1 88.021(9) 4_565 . ?
N1 Zn1 Zn1 180.0 . 5_655 ?
O1 Zn1 Zn1 79.29(2) 2_665 5_655 ?
O1 Zn1 Zn1 79.29(2) 3_655 5_655 ?
O1 Zn1 Zn1 79.29(2) 4_565 5_655 ?
O1 Zn1 Zn1 79.29(2) . 5_655 ?
C1 O1 Zn1 123.12(8) . . ?
O1 C1 O1 126.31(14) . 7 ?
O1 C1 C2 116.84(7) . . ?
O1 C1 C2 116.84(7) 7 . ?
C3 C2 C3 121.67(14) 7 . ?
C3 C2 C1 119.16(7) 7 . ?
C3 C2 C1 119.16(7) . . ?
C2 C3 C3 119.16(7) . 31_665 ?
C2 C3 C4 122.08(11) . . ?
C3 C3 C4 118.76(7) 31_665 . ?
C5 C4 C3 120.60(13) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C5 120.64(9) . 31_665 ?
C4 C5 H5A 119.7 . . ?
C5 C5 H5A 119.7 31_665 . ?
C8 N1 C7 109.7(4) . . ?
C8 N1 C6 108.5(4) . . ?
C7 N1 C6 107.3(4) . . ?
C8 N1 Zn1 110.4(2) . . ?
C7 N1 Zn1 110.4(2) . . ?
C6 N1 Zn1 110.3(2) . . ?
N1 C6 C6 110.3(2) . 18 ?
N1 C6 H6A 109.6 . . ?
C6 C6 H6A 109.6 18 . ?
N1 C6 H6B 109.6 . . ?
C6 C6 H6B 109.6 18 . ?
H6A C6 H6B 108.1 . . ?
N1 C7 C7 110.4(2) . 18 ?
N1 C7 H7A 109.6 . . ?
C7 C7 H7A 109.6 18 . ?
N1 C7 H7B 109.6 . . ?
C7 C7 H7B 109.6 18 . ?
H7A C7 H7B 108.1 . . ?
N1 C8 C8 110.4(2) . 18 ?
N1 C8 H8A 109.6 . . ?
C8 C8 H8A 109.6 18 . ?
N1 C8 H8B 109.6 . . ?
C8 C8 H8B 109.6 18 . ?
H8A C8 H8B 108.1 . . ?

_refine_diff_density_max         0.999
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.069




