# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_nn
_database_code_depnum_ccdc_archive 'CCDC 1400657'
_audit_update_record             
;
2015-05-13 deposited with the CCDC.
2018-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H4 N4 O4 Zn'
_chemical_formula_sum            'C9 H4 N4 O4 Zn'
_chemical_formula_weight         297.53

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.345(5)
_cell_length_b                   9.502(5)
_cell_length_c                   18.610(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 99.448(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2153.4(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.918
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    1.147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.758
_exptl_absorpt_correction_T_max  0.777
_exptl_absorpt_process_details   'SADABS(Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11092
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         25.20
_reflns_number_total             3870
_reflns_number_gt                2932
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97(Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 1990)'
_computing_publication_material  SHELXL-97

_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     
'calc w=1/[σ²(Fo²)+(0.1982P)²+0.8998P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3870
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0806
_refine_ls_wR_factor_ref         0.2790
_refine_ls_wR_factor_gt          0.2592
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2952(5) 0.1920(7) -0.0420(3) 0.0502(15) Uani 1 1 d . . .
C2 C 0.3896(5) 0.1147(8) -0.0515(3) 0.0530(16) Uani 1 1 d . . .
H2 H 0.4117 0.1141 -0.0969 0.064 Uiso 1 1 calc R . .
C3 C 0.4499(5) 0.0400(7) 0.0051(3) 0.0495(15) Uani 1 1 d . . .
C4 C 0.4138(5) 0.0412(7) 0.0727(3) 0.0507(16) Uani 1 1 d . . .
H4 H 0.4521 -0.0099 0.1113 0.061 Uiso 1 1 calc R . .
C5 C 0.3213(5) 0.1177(7) 0.0828(3) 0.0488(15) Uani 1 1 d . . .
C6 C 0.2635(5) 0.1941(8) 0.0255(3) 0.0543(16) Uani 1 1 d . . .
H6 H 0.2029 0.2471 0.0327 0.065 Uiso 1 1 calc R . .
C7 C 0.2843(5) 0.1139(8) 0.1562(3) 0.0526(16) Uani 1 1 d . . .
C8 C 0.2289(6) 0.2674(8) -0.1042(3) 0.0572(18) Uani 1 1 d . . .
N2 N 0.0888(4) -0.0369(5) 0.2601(3) 0.0451(11) Uani 1 1 d . . .
C9 C -0.0097(6) -0.0794(7) 0.2498(4) 0.0573(19) Uani 1 1 d . . .
N1 N 0.1465(7) -0.1500(8) 0.2786(10) 0.165(6) Uani 1 1 d . . .
H1 H 0.2168 -0.1524 0.2904 0.198 Uiso 1 1 calc R . .
O1 O 0.3331(5) 0.0401(7) 0.2050(3) 0.0881(19) Uani 1 1 d . . .
O2 O 0.2007(4) 0.1854(5) 0.1625(2) 0.0540(11) Uani 1 1 d . . .
O3 O 0.1475(6) 0.3343(7) -0.0947(3) 0.105(3) Uani 1 1 d . . .
O4 O 0.2592(4) 0.2579(5) -0.1657(2) 0.0596(13) Uani 1 1 d . . .
Zn1 Zn 0.15512(5) 0.15629(7) 0.25726(3) 0.0390(3) Uani 1 1 d . . .
N4 N -0.0204(4) -0.2150(6) 0.2545(3) 0.0496(13) Uani 1 1 d . . .
N3 N 0.0821(7) -0.2580(8) 0.2764(7) 0.145(5) Uani 1 1 d . . .
H3 H -0.049(6) -0.015(8) 0.240(4) 0.06(2) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.052(4) 0.069(4) 0.032(3) 0.005(3) 0.013(3) 0.017(3)
C2 0.051(4) 0.084(5) 0.027(3) 0.009(3) 0.016(3) 0.018(3)
C3 0.046(3) 0.076(4) 0.028(3) 0.007(3) 0.012(2) 0.014(3)
C4 0.044(3) 0.082(5) 0.028(3) 0.012(3) 0.012(2) 0.016(3)
C5 0.044(3) 0.075(4) 0.029(3) 0.004(3) 0.010(2) 0.010(3)
C6 0.049(4) 0.078(4) 0.038(3) 0.006(3) 0.015(3) 0.018(3)
C7 0.052(4) 0.073(4) 0.036(3) -0.002(3) 0.017(3) 0.008(3)
C8 0.055(4) 0.077(5) 0.043(3) 0.009(3) 0.016(3) 0.025(3)
N2 0.049(3) 0.038(3) 0.049(3) 0.002(2) 0.008(2) 0.000(2)
C9 0.048(4) 0.035(4) 0.092(6) 0.002(3) 0.021(4) 0.004(3)
N1 0.055(5) 0.063(6) 0.36(2) 0.043(7) -0.005(8) -0.007(4)
O1 0.086(4) 0.143(5) 0.039(3) 0.031(3) 0.021(2) 0.047(4)
O2 0.056(3) 0.074(3) 0.037(2) -0.001(2) 0.022(2) 0.010(2)
O3 0.108(5) 0.164(7) 0.048(3) 0.022(3) 0.027(3) 0.087(5)
O4 0.059(3) 0.087(4) 0.035(2) 0.015(2) 0.0119(19) 0.028(2)
Zn1 0.0439(5) 0.0435(5) 0.0312(5) -0.0037(2) 0.0109(3) -0.0051(3)
N4 0.046(3) 0.050(3) 0.056(3) 0.007(2) 0.018(2) 0.000(2)
N3 0.065(5) 0.058(5) 0.304(14) 0.045(7) 0.007(7) 0.001(4)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C6 1.376(8) . ?
C1 C2 1.413(9) . ?
C1 C8 1.487(8) . ?
C2 C3 1.382(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.402(7) . ?
C3 C3 1.492(11) 3_655 ?
C4 C5 1.392(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(9) . ?
C5 C7 1.510(8) . ?
C6 H6 0.9300 . ?
C7 O1 1.225(8) . ?
C7 O2 1.258(8) . ?
C8 O3 1.227(8) . ?
C8 O4 1.264(7) . ?
N2 C9 1.265(8) . ?
N2 N1 1.304(9) . ?
N2 Zn1 2.015(5) . ?
C9 N4 1.300(9) . ?
C9 H3 0.78(8) . ?
N1 N3 1.294(10) . ?
N1 H1 0.8600 . ?
O2 Zn1 1.956(4) . ?
O4 Zn1 1.940(4) 4_565 ?
Zn1 O4 1.940(4) 4_566 ?
Zn1 N4 2.047(5) 2 ?
N4 N3 1.328(9) . ?
N4 Zn1 2.047(5) 2_545 ?

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
C6 C1 C2 119.0(6) . . ?
C6 C1 C8 120.1(5) . . ?
C2 C1 C8 120.9(5) . . ?
C3 C2 C1 121.6(5) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 118.0(5) . . ?
C2 C3 C3 121.3(6) . 3_655 ?
C4 C3 C3 120.7(6) . 3_655 ?
C5 C4 C3 120.9(5) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C6 C5 C4 119.9(5) . . ?
C6 C5 C7 121.0(5) . . ?
C4 C5 C7 119.1(5) . . ?
C1 C6 C5 120.5(6) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O1 C7 O2 123.4(6) . . ?
O1 C7 C5 120.0(6) . . ?
O2 C7 C5 116.5(6) . . ?
O3 C8 O4 122.6(6) . . ?
O3 C8 C1 119.8(6) . . ?
O4 C8 C1 117.6(5) . . ?
C9 N2 N1 104.3(6) . . ?
C9 N2 Zn1 132.2(5) . . ?
N1 N2 Zn1 123.4(5) . . ?
N2 C9 N4 114.3(6) . . ?
N2 C9 H3 109(6) . . ?
N4 C9 H3 137(6) . . ?
N3 N1 N2 109.8(7) . . ?
N3 N1 H1 125.1 . . ?
N2 N1 H1 125.1 . . ?
C7 O2 Zn1 111.7(4) . . ?
C8 O4 Zn1 112.4(4) . 4_565 ?
O4 Zn1 O2 110.69(19) 4_566 . ?
O4 Zn1 N2 125.9(2) 4_566 . ?
O2 Zn1 N2 109.3(2) . . ?
O4 Zn1 N4 104.8(2) 4_566 2 ?
O2 Zn1 N4 99.6(2) . 2 ?
N2 Zn1 N4 102.7(2) . 2 ?
C9 N4 N3 102.9(6) . . ?
C9 N4 Zn1 132.4(5) . 2_545 ?
N3 N4 Zn1 124.5(5) . 2_545 ?
N1 N3 N4 108.4(7) . . ?

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 C1 C2 C3 0.8(12) . . . . ?
C8 C1 C2 C3 -177.7(7) . . . . ?
C1 C2 C3 C4 0.9(11) . . . . ?
C1 C2 C3 C3 -179.3(8) . . . 3_655 ?
C2 C3 C4 C5 -1.3(11) . . . . ?
C3 C3 C4 C5 178.9(8) 3_655 . . . ?
C3 C4 C5 C6 0.1(11) . . . . ?
C3 C4 C5 C7 179.0(6) . . . . ?
C2 C1 C6 C5 -2.1(11) . . . . ?
C8 C1 C6 C5 176.4(7) . . . . ?
C4 C5 C6 C1 1.7(11) . . . . ?
C7 C5 C6 C1 -177.2(7) . . . . ?
C6 C5 C7 O1 176.3(8) . . . . ?
C4 C5 C7 O1 -2.7(11) . . . . ?
C6 C5 C7 O2 -1.4(10) . . . . ?
C4 C5 C7 O2 179.7(7) . . . . ?
C6 C1 C8 O3 1.8(12) . . . . ?
C2 C1 C8 O3 -179.7(8) . . . . ?
C6 C1 C8 O4 -177.4(7) . . . . ?
C2 C1 C8 O4 1.0(11) . . . . ?
N1 N2 C9 N4 -5.2(11) . . . . ?
Zn1 N2 C9 N4 178.3(4) . . . . ?
C9 N2 N1 N3 2.3(16) . . . . ?
Zn1 N2 N1 N3 179.2(9) . . . . ?
O1 C7 O2 Zn1 -2.9(10) . . . . ?
C5 C7 O2 Zn1 174.7(5) . . . . ?
O3 C8 O4 Zn1 -5.9(10) . . . 4_565 ?
C1 C8 O4 Zn1 173.4(5) . . . 4_565 ?
C7 O2 Zn1 O4 70.6(5) . . . 4_566 ?
C7 O2 Zn1 N2 -72.2(5) . . . . ?
C7 O2 Zn1 N4 -179.4(5) . . . 2 ?
C9 N2 Zn1 O4 126.4(6) . . . 4_566 ?
N1 N2 Zn1 O4 -49.6(11) . . . 4_566 ?
C9 N2 Zn1 O2 -97.9(7) . . . . ?
N1 N2 Zn1 O2 86.1(10) . . . . ?
C9 N2 Zn1 N4 7.2(7) . . . 2 ?
N1 N2 Zn1 N4 -168.8(10) . . . 2 ?
N2 C9 N4 N3 5.9(9) . . . . ?
N2 C9 N4 Zn1 -179.4(5) . . . 2_545 ?
N2 N1 N3 N4 1.2(18) . . . . ?
C9 N4 N3 N1 -4.0(14) . . . . ?
Zn1 N4 N3 N1 -179.3(10) 2_545 . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.588
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.277
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.015 -0.017 0.004 1290 379 ' '
_platon_squeeze_details          
;
;
