# Electronic Supplementary Material (ESI) for ChemComm.
# 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_DG1
_database_code_depnum_ccdc_archive 'CCDC 2351712'
loop_
_audit_author_name
_audit_author_address
'Debajyoti Ghoshal'
;Jadavpur University
India
;
_audit_update_record             
;
2024-04-28 deposited with the CCDC.	2024-07-09 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT306_DG1                 
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) ....... O1W
RESPONSE: Due to disorderness, hydrogen can not be placed here.
However, it represents the best possible structure.
;
_vrf_PLAT315_DG1                 
;
PROBLEM: Singly Bonded Carbon Detected (H-atoms Missing). C1S
RESPONSE: Due to disorderness, hydrogen can not be placed here.
However, it represents the best possible structure.
;
_vrf_PLAT430_DG1                 
;
PROBLEM: Short Inter D...A Contact O1W ..O3W . 2.81 Ang.
RESPONSE: Due to hydrogen bonding between these two oxygen atom,
they are in close contact but, due to disorderness 
hydrogen can not be placed here. However,
it represents the best possible structure.
;
# end validation reply form

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H8 N4 O9 Zn'
_chemical_formula_weight         465.63

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.0263(14)
_cell_length_b                   8.9753(15)
_cell_length_c                   13.924(3)
_cell_angle_alpha                95.081(5)
_cell_angle_beta                 93.392(5)
_cell_angle_gamma                92.034(5)
_cell_volume                     996.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    250
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      27.8

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    1.288
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_T_max  0.884
_exptl_absorpt_process_details   
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;
_exptl_absorpt_special_details   
;
?
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35191
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.599
_diffrn_reflns_theta_max         27.513
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4576
_reflns_number_gt                4083
_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       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'
_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 > 2σ(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     
'w=1/[σ²(Fo²)+(0.0765P)²+0.8135P] 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         4576
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1292
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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 0.47888(4) 0.06906(3) 0.73453(2) 0.03426(13) Uani 1 1 d . . . . .
O6 O 1.1356(3) 0.2783(2) 0.47020(17) 0.0449(5) Uani 1 1 d . . . . .
O3 O 0.6510(3) -0.1418(3) 0.6282(2) 0.0614(7) Uani 1 1 d . . . . .
O2 O 0.7252(4) 0.2494(3) 0.8756(2) 0.0694(8) Uani 1 1 d . . . . .
O4 O 0.6361(3) 0.1041(3) 0.63507(18) 0.0516(6) Uani 1 1 d . . . . .
O1 O 0.6181(3) 0.0170(3) 0.84586(18) 0.0548(6) Uani 1 1 d . . . . .
N3 N 0.1560(3) 0.6940(3) 0.68498(18) 0.0361(5) Uani 1 1 d . . . . .
N4 N 0.2959(3) 0.9080(3) 0.71786(18) 0.0378(5) Uani 1 1 d . . . . .
N1 N 0.3461(3) 0.2543(3) 0.75051(18) 0.0370(5) Uani 1 1 d . . . . .
O5 O 1.0211(3) -0.3066(3) 1.00157(19) 0.0556(6) Uani 1 1 d . . . . .
N2 N 0.1904(3) 0.4345(3) 0.70733(18) 0.0373(5) Uani 1 1 d . . . . .
O1W O 0.7273(6) 0.4793(6) 0.7371(4) 0.1299(19) Uani 1 1 d . . . . .
O3W O 0.6266(7) 0.4117(6) 0.5408(4) 0.144(2) Uani 1 1 d . . . . .
C6 C 0.8564(3) -0.0080(3) 0.5514(2) 0.0365(6) Uani 1 1 d . . . . .
C10 C 0.3046(3) 0.3370(3) 0.6800(2) 0.0356(6) Uani 1 1 d . . . . .
H10 H 0.348661 0.328822 0.619559 0.043 Uiso 1 1 calc R U . . .
C8 C 1.0707(4) 0.1396(3) 0.4846(2) 0.0357(6) Uani 1 1 d . . . . .
C14 C 0.2948(3) 0.7742(3) 0.6702(2) 0.0367(6) Uani 1 1 d . . . . .
H14 H 0.378793 0.740121 0.631631 0.044 Uiso 1 1 calc R U . . .
C7 C 0.9294(4) 0.1305(3) 0.5356(2) 0.0387(6) Uani 1 1 d . . . . .
H7 H 0.881916 0.217971 0.559883 0.046 Uiso 1 1 calc R U . . .
C2 C 0.8662(4) 0.0552(4) 0.9468(2) 0.0391(6) Uani 1 1 d . . . . .
C13 C 0.0628(4) 0.7811(4) 0.7446(3) 0.0508(8) Uani 1 1 d . . . . .
H13 H -0.039691 0.754599 0.767500 0.061 Uiso 1 1 calc R U . . .
C5 C 0.7043(4) -0.0167(4) 0.6078(2) 0.0436(7) Uani 1 1 d . . . . .
C3 C 0.8805(4) -0.0980(4) 0.9511(2) 0.0408(6) Uani 1 1 d . . . . .
H3 H 0.799604 -0.163721 0.918687 0.049 Uiso 1 1 calc R U . . .
C4 C 1.0135(4) -0.1548(4) 1.0029(2) 0.0403(6) Uani 1 1 d . . . . .
C1 C 0.7274(4) 0.1130(4) 0.8859(2) 0.0474(7) Uani 1 1 d . . . . .
C12 C 0.1131(4) 0.5407(3) 0.6456(2) 0.0412(6) Uani 1 1 d . . . . .
C15 C 0.1489(4) 0.9132(4) 0.7637(3) 0.0517(8) Uani 1 1 d . . . . .
H15 H 0.114155 0.995137 0.802013 0.062 Uiso 1 1 calc R U . . .
C11 C 0.1570(5) 0.4129(4) 0.8005(3) 0.0538(8) Uani 1 1 d . . . . .
H11 H 0.082264 0.464345 0.838356 0.065 Uiso 1 1 calc R U . . .
C9 C 0.2543(5) 0.3021(4) 0.8263(2) 0.0505(8) Uani 1 1 d . . . . .
H9 H 0.258493 0.263988 0.886291 0.061 Uiso 1 1 calc R U . . .
C1S C 0.5590(9) -0.3123(8) 0.8262(5) 0.1019(18) Uiso 1 1 d . . . . .
O1S O 0.4771(18) -0.3199(15) 0.9147(11) 0.321(6) Uiso 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 O1 1.957(2) . ?
Zn1 O4 1.966(2) . ?
Zn1 N1 2.010(2) . ?
Zn1 N4 2.012(2) 1_545 ?
O6 C8 1.368(3) . ?
O3 C5 1.249(4) . ?
O2 C1 1.246(4) . ?
O4 C5 1.271(4) . ?
O1 C1 1.275(4) . ?
N3 C14 1.341(4) . ?
N3 C13 1.364(4) . ?
N3 C12 1.457(4) . ?
N4 C14 1.320(4) . ?
N4 C15 1.375(4) . ?
N1 C10 1.317(4) . ?
N1 C9 1.369(4) . ?
O5 C4 1.365(4) . ?
N2 C10 1.338(4) . ?
N2 C11 1.369(4) . ?
N2 C12 1.468(4) . ?
C6 C7 1.396(4) . ?
C6 C8 1.403(4) 2_756 ?
C6 C5 1.493(4) . ?
C8 C7 1.377(4) . ?
C2 C3 1.390(5) . ?
C2 C4 1.403(4) 2_757 ?
C2 C1 1.496(4) . ?
C13 C15 1.349(5) . ?
C3 C4 1.390(4) . ?
C11 C9 1.346(5) . ?
C1S O1S 1.437(14) . ?

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 105.07(11) . . ?
O1 Zn1 N1 117.93(11) . . ?
O4 Zn1 N1 106.14(10) . . ?
O1 Zn1 N4 104.02(11) . 1_545 ?
O4 Zn1 N4 123.42(11) . 1_545 ?
N1 Zn1 N4 101.26(10) . 1_545 ?
C5 O4 Zn1 110.4(2) . . ?
C1 O1 Zn1 119.0(2) . . ?
C14 N3 C13 107.7(2) . . ?
C14 N3 C12 126.3(3) . . ?
C13 N3 C12 126.0(3) . . ?
C14 N4 C15 105.8(2) . . ?
C14 N4 Zn1 129.0(2) . 1_565 ?
C15 N4 Zn1 124.9(2) . 1_565 ?
C10 N1 C9 106.1(2) . . ?
C10 N1 Zn1 124.3(2) . . ?
C9 N1 Zn1 128.3(2) . . ?
C10 N2 C11 107.6(3) . . ?
C10 N2 C12 125.0(3) . . ?
C11 N2 C12 127.3(3) . . ?
C7 C6 C8 119.4(3) . 2_756 ?
C7 C6 C5 120.6(3) . . ?
C8 C6 C5 120.0(3) 2_756 . ?
N1 C10 N2 110.6(3) . . ?
O6 C8 C7 118.5(3) . . ?
O6 C8 C6 121.9(3) . 2_756 ?
C7 C8 C6 119.7(3) . 2_756 ?
N4 C14 N3 110.7(3) . . ?
C8 C7 C6 121.0(3) . . ?
C3 C2 C4 119.5(3) . 2_757 ?
C3 C2 C1 120.2(3) . . ?
C4 C2 C1 120.3(3) 2_757 . ?
C15 C13 N3 106.3(3) . . ?
O3 C5 O4 122.4(3) . . ?
O3 C5 C6 119.0(3) . . ?
O4 C5 C6 118.6(3) . . ?
C2 C3 C4 121.3(3) . . ?
O5 C4 C3 117.8(3) . . ?
O5 C4 C2 123.0(3) . 2_757 ?
C3 C4 C2 119.2(3) . 2_757 ?
O2 C1 O1 123.7(3) . . ?
O2 C1 C2 119.4(3) . . ?
O1 C1 C2 117.0(3) . . ?
N3 C12 N2 110.3(2) . . ?
C13 C15 N4 109.4(3) . . ?
C9 C11 N2 106.1(3) . . ?
C11 C9 N1 109.5(3) . . ?

_refine_diff_density_max         1.015
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.082



