# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1968474'
loop_
_audit_author_name
_audit_author_address
'M.R. Prathapachandra Kurup'
; Cochin University of Science and Technology
India
;
_audit_update_record             
;
2019-11-27 deposited with the CCDC.	2020-01-07 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         'C16 H14 N6 O2 Zn, 4(H O0.50)'
_chemical_formula_sum            'C16 H20 N6 O5 Zn'
_chemical_formula_weight         441.77

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'
Na Na 0.0362 0.0249 '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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

_cell_length_a                   12.9000(13)
_cell_length_b                   12.0879(12)
_cell_length_c                   12.4494(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1941.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7980
_cell_measurement_theta_min      2.2905
_cell_measurement_theta_max      28.2615

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   0.639
_exptl_transmission_factor_max   0.676
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    1.306
_shelx_estimated_absorpt_T_min   0.658
_shelx_estimated_absorpt_T_max   0.695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker AXS Kappa Apex2 diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21393
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.158
_diffrn_reflns_theta_max         26.677
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2056
_reflns_number_gt                1554
_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       ?
_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+0.9746P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2048
_refine_ls_number_parameters     145
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.500000 0.17949(3) 0.250000 0.02029(14) Uani 1 2 d S T P . .
O1 O 0.39839(12) 0.23828(13) 0.38631(13) 0.0315(4) Uani 1 1 d . . . . .
N1 N 0.11755(14) 0.26024(16) 0.65324(14) 0.0256(4) Uani 1 1 d . . . . .
N2 N 0.35761(15) 0.05242(16) 0.40426(14) 0.0284(5) Uani 1 1 d . . . . .
N3 N 0.43084(14) 0.04073(15) 0.32286(13) 0.0242(4) Uani 1 1 d . . . . .
C1 C 0.2039(2) 0.3175(2) 0.6380(2) 0.0371(6) Uani 1 1 d . . . . .
H1 H 0.213036 0.382576 0.676665 0.045 Uiso 1 1 calc R U . . .
C2 C 0.28072(19) 0.2856(2) 0.5680(2) 0.0372(6) Uani 1 1 d . . . . .
H2 H 0.339313 0.329426 0.558832 0.045 Uiso 1 1 calc R U . . .
C3 C 0.27015(18) 0.18837(19) 0.51174(18) 0.0260(5) Uani 1 1 d . . . . .
C4 C 0.1824(2) 0.1262(2) 0.5303(2) 0.0366(6) Uani 1 1 d . . . . .
H4 H 0.173596 0.058466 0.496042 0.044 Uiso 1 1 calc R U . . .
C5 C 0.1082(2) 0.1647(2) 0.5995(2) 0.0354(6) Uani 1 1 d . . . . .
H5 H 0.048572 0.122735 0.609562 0.042 Uiso 1 1 calc R U . . .
C6 C 0.34856(18) 0.15924(19) 0.42760(18) 0.0249(5) Uani 1 1 d . . . . .
C7 C 0.46177(19) -0.0559(2) 0.29525(19) 0.0286(5) Uani 1 1 d . . . . .
C8 C 0.4283(3) -0.1608(2) 0.3466(3) 0.0542(9) Uani 1 1 d . . . . .
H8A H 0.408947 -0.146764 0.419780 0.065 Uiso 1 1 calc R U . . .
H8B H 0.484342 -0.213028 0.344855 0.065 Uiso 1 1 calc R U . . .
H8C H 0.369989 -0.190459 0.308303 0.065 Uiso 1 1 calc R U . . .
O2 O 0.3332(2) 0.4494(2) 0.3205(2) 0.0724(7) Uani 1 1 d D . . . .
H2A H 0.278(2) 0.472(4) 0.352(3) 0.109 Uiso 1 1 d D U . . .
H2B H 0.345(4) 0.385(2) 0.349(3) 0.109 Uiso 1 1 d D U . . .
O3 O 0.4824(8) 0.5823(4) 0.2152(9) 0.101(3) Uani 0.5 1 d D . P A -1
H3A H 0.435(6) 0.550(11) 0.250(9) 0.151 Uiso 0.5 1 d D U P B -1
H3B H 0.532(7) 0.535(9) 0.214(10) 0.151 Uiso 0.5 1 d D U P C -1


_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 2.0691(18) 3_556 ?
Zn1 N1 2.0691(18) 2_554 ?
Zn1 N3 2.1053(18) . ?
Zn1 N3 2.1054(18) 4_655 ?
Zn1 O1 2.2589(15) . ?
Zn1 O1 2.2590(15) 4_655 ?
O1 C6 1.261(3) . ?
N1 C1 1.325(3) . ?
N1 C5 1.340(3) . ?
N2 C6 1.329(3) . ?
N2 N3 1.393(2) . ?
N3 C7 1.281(3) . ?
C1 C2 1.374(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(3) . ?
C3 C6 1.498(3) . ?
C4 C5 1.369(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C7 C8 1.485(3) . ?
C7 C7 1.497(5) 4_655 ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
O2 H2A 0.855(18) . ?
O2 H2B 0.869(19) . ?
O3 H3A 0.85(2) . ?
O3 H3B 0.85(2) . ?

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 N1 138.77(11) 3_556 2_554 ?
N1 Zn1 N3 109.89(7) 3_556 . ?
N1 Zn1 N3 102.75(7) 2_554 . ?
N1 Zn1 N3 102.75(7) 3_556 4_655 ?
N1 Zn1 N3 109.89(7) 2_554 4_655 ?
N3 Zn1 N3 74.36(10) . 4_655 ?
N1 Zn1 O1 82.94(7) 3_556 . ?
N1 Zn1 O1 84.34(7) 2_554 . ?
N3 Zn1 O1 71.40(6) . . ?
N3 Zn1 O1 145.10(7) 4_655 . ?
N1 Zn1 O1 84.34(7) 3_556 4_655 ?
N1 Zn1 O1 82.94(7) 2_554 4_655 ?
N3 Zn1 O1 145.10(7) . 4_655 ?
N3 Zn1 O1 71.40(6) 4_655 4_655 ?
O1 Zn1 O1 143.33(8) . 4_655 ?
C6 O1 Zn1 111.32(14) . . ?
C1 N1 C5 117.0(2) . . ?
C1 N1 Zn1 121.05(16) . 2 ?
C5 N1 Zn1 121.88(16) . 2 ?
C6 N2 N3 108.50(17) . . ?
C7 N3 N2 119.95(18) . . ?
C7 N3 Zn1 118.59(15) . . ?
N2 N3 Zn1 121.34(13) . . ?
N1 C1 C2 123.4(2) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C1 C2 C3 119.4(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 117.5(2) . . ?
C2 C3 C6 119.4(2) . . ?
C4 C3 C6 122.9(2) . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 123.0(2) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
O1 C6 N2 127.0(2) . . ?
O1 C6 C3 116.8(2) . . ?
N2 C6 C3 116.14(19) . . ?
N3 C7 C8 124.9(2) . . ?
N3 C7 C7 114.03(13) . 4_655 ?
C8 C7 C7 121.03(15) . 4_655 ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
H2A O2 H2B 104(4) . . ?
H3A O3 H3B 104(3) . . ?

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
C6 N2 N3 C7 171.9(2) . . . . ?
C6 N2 N3 Zn1 -4.0(2) . . . . ?
C5 N1 C1 C2 2.4(4) . . . . ?
Zn1 N1 C1 C2 -174.6(2) 2 . . . ?
N1 C1 C2 C3 -1.5(4) . . . . ?
C1 C2 C3 C4 -1.1(4) . . . . ?
C1 C2 C3 C6 174.0(2) . . . . ?
C2 C3 C4 C5 2.6(4) . . . . ?
C6 C3 C4 C5 -172.3(2) . . . . ?
C1 N1 C5 C4 -0.8(4) . . . . ?
Zn1 N1 C5 C4 176.2(2) 2 . . . ?
C3 C4 C5 N1 -1.7(4) . . . . ?
Zn1 O1 C6 N2 5.6(3) . . . . ?
Zn1 O1 C6 C3 -174.08(15) . . . . ?
N3 N2 C6 O1 -1.5(3) . . . . ?
N3 N2 C6 C3 178.14(18) . . . . ?
C2 C3 C6 O1 -23.8(3) . . . . ?
C4 C3 C6 O1 151.0(2) . . . . ?
C2 C3 C6 N2 156.5(2) . . . . ?
C4 C3 C6 N2 -28.8(3) . . . . ?
N2 N3 C7 C8 -2.4(4) . . . . ?
Zn1 N3 C7 C8 173.7(2) . . . . ?
N2 N3 C7 C7 178.4(2) . . . 4_655 ?
Zn1 N3 C7 C7 -5.6(4) . . . 4_655 ?

_refine_diff_density_max         0.447
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.061


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMF'
_chemical_properties_physical    Heat-sensitive
_exptl_crystal_preparation       Luminescent,Thermochromic
