# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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. 
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data_KS130314_0m
_database_code_depnum_ccdc_archive 'CCDC 1571975'
_audit_update_record             
;
2017-09-01 deposited with the CCDC.
2017-12-17 downloaded from the CCDC.
;
_audit_creation_date             2015-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H13 N5 O4 Zn, 2(H2 O)'
_chemical_formula_sum            'C18 H17 N5 O6 Zn'
_chemical_formula_weight         464.73
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.617(8)
_cell_length_b                   22.95(2)
_cell_length_c                   10.243(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.365(15)
_cell_angle_gamma                90
_cell_volume                     1978(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    597
_cell_measurement_temperature    100
_cell_measurement_theta_max      16.51
_cell_measurement_theta_min      2.95
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.288
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0928 before and 0.0697 after correction. The Ratio of minimum to maximum transmission is 0.8545. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1647
_diffrn_reflns_av_unetI/netI     0.1503
_diffrn_reflns_Laue_measured_fraction_full 0.797
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12204
_diffrn_reflns_point_group_measured_fraction_full 0.797
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         23.322
_diffrn_reflns_theta_min         1.775
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.797
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1587
_reflns_number_total             2855
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.833
_refine_diff_density_rms         0.138
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         2855
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1372
_refine_ls_R_factor_gt           0.0597
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0825P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1312
_refine_ls_wR_factor_ref         0.1807
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O6(H6A,H6B), O5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C13(H13), C9(H9), C11(H11), C10(H10), C12(H12), C14(H14), C18(H18),
 C15(H15), C17(H17), C16(H16), C6(H6), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.06883(13) 0.59586(4) 0.57017(10) 0.0225(3) Uani 1 1 d . . . . .
O1 O 0.1435(6) 0.5515(2) 0.7358(5) 0.0211(14) Uani 1 1 d . . . . .
O2 O 0.0136(7) 0.6211(3) 0.8211(5) 0.0240(15) Uani 1 1 d . . . . .
C1 C 0.2890(10) 0.4739(4) 1.1093(8) 0.022(2) Uani 1 1 d . . . . .
C7 C 0.0965(10) 0.5765(4) 0.8329(8) 0.020(2) Uani 1 1 d . . . . .
C2 C 0.2444(10) 0.4994(4) 0.9837(8) 0.022(2) Uani 1 1 d . . . . .
H2 H 0.2794 0.4834 0.9094 0.026 Uiso 1 1 calc R . . . .
C3 C 0.1483(10) 0.5484(4) 0.9683(8) 0.019(2) Uani 1 1 d . . . . .
N2 N 0.4288(9) 0.4006(4) 1.0384(8) 0.034(2) Uani 1 1 d . . . . .
N1 N 0.3868(9) 0.4229(3) 1.1373(7) 0.033(2) Uani 1 1 d . . . . .
N3 N 0.4777(10) 0.3768(4) 0.9591(9) 0.049(3) Uani 1 1 d . . . . .
N4 N -0.1663(8) 0.6071(3) 0.5145(7) 0.0245(18) Uani 1 1 d . . . . .
C13 C -0.2408(11) 0.6519(4) 0.5602(8) 0.029(2) Uani 1 1 d . . . . .
H13 H -0.1787 0.6784 0.6210 0.034 Uiso 1 1 calc R . . . .
C9 C -0.2577(13) 0.5705(4) 0.4260(9) 0.033(3) Uani 1 1 d . . . . .
H9 H -0.2076 0.5393 0.3902 0.039 Uiso 1 1 calc R . . . .
C11 C -0.4919(13) 0.6229(6) 0.4368(11) 0.051(3) Uani 1 1 d . . . . .
H11 H -0.6038 0.6279 0.4113 0.061 Uiso 1 1 calc R . . . .
C10 C -0.4178(13) 0.5766(4) 0.3863(10) 0.040(3) Uani 1 1 d . . . . .
H10 H -0.4781 0.5497 0.3252 0.048 Uiso 1 1 calc R . . . .
C12 C -0.4006(12) 0.6612(5) 0.5239(9) 0.036(3) Uani 1 1 d . . . . .
H12 H -0.4479 0.6936 0.5582 0.043 Uiso 1 1 calc R . . . .
N5 N 0.1880(9) 0.6725(3) 0.6045(7) 0.0240(19) Uani 1 1 d . . . . .
C14 C 0.1508(11) 0.7208(4) 0.5281(9) 0.029(2) Uani 1 1 d . . . . .
H14 H 0.0705 0.7181 0.4487 0.035 Uiso 1 1 calc R . . . .
C18 C 0.2241(13) 0.7736(4) 0.5601(10) 0.037(3) Uani 1 1 d . . . . .
H18 H 0.1936 0.8064 0.5041 0.044 Uiso 1 1 calc R . . . .
C15 C 0.3060(12) 0.6794(4) 0.7159(9) 0.033(3) Uani 1 1 d . . . . .
H15 H 0.3366 0.6465 0.7717 0.039 Uiso 1 1 calc R . . . .
C17 C 0.3423(14) 0.7788(5) 0.6742(10) 0.044(3) Uani 1 1 d . . . . .
H17 H 0.3944 0.8149 0.6980 0.053 Uiso 1 1 calc R . . . .
C16 C 0.3819(13) 0.7306(5) 0.7516(10) 0.045(3) Uani 1 1 d . . . . .
H16 H 0.4628 0.7328 0.8307 0.054 Uiso 1 1 calc R . . . .
C6 C 0.2416(10) 0.4979(4) 1.2190(8) 0.022(2) Uani 1 1 d . . . . .
H6 H 0.2718 0.4800 1.3044 0.027 Uiso 1 1 calc R . . . .
C4 C 0.1047(9) 0.5734(4) 1.0778(8) 0.019(2) Uani 1 1 d . . . . .
H4 H 0.0434 0.6081 1.0674 0.022 Uiso 1 1 calc R . . . .
C5 C 0.1503(10) 0.5477(4) 1.2032(8) 0.022(2) Uani 1 1 d . . . . .
O4 O 0.0362(8) 0.6245(3) 0.3069(6) 0.0330(17) Uani 1 1 d . . . . .
O3 O 0.1362(7) 0.5485(3) 0.4321(5) 0.0259(15) Uani 1 1 d . . . . .
O6 O 0.1678(7) 0.2859(2) 0.8049(6) 0.0434(19) Uani 1 1 d . . . . .
H6A H 0.2571 0.3010 0.8023 0.065 Uiso 1 1 d G . . . .
H6B H 0.1501 0.2896 0.8830 0.065 Uiso 1 1 d G . . . .
O5 O 0.8009(7) 0.7060(2) 0.9056(6) 0.0378(18) Uani 1 1 d . . . . .
H5A H 0.8700 0.6805 0.8982 0.057 Uiso 1 1 d G . . . .
H5B H 0.8019 0.7330 0.8490 0.057 Uiso 1 1 d G . . . .
C8 C 0.1020(11) 0.5769(4) 0.3194(9) 0.027(2) Uani 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 1.965(5) . ?
Zn1 N4 2.000(7) . ?
Zn1 N5 2.028(7) . ?
Zn1 O3 1.968(6) . ?
O1 C7 1.288(9) . ?
O2 C7 1.238(10) . ?
C1 C2 1.391(11) . ?
C1 N1 1.434(11) . ?
C1 C6 1.389(11) . ?
C7 C3 1.509(11) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(12) . ?
C3 C4 1.381(11) . ?
N2 N1 1.255(11) . ?
N2 N3 1.132(10) . ?
N4 C13 1.347(11) . ?
N4 C9 1.357(11) . ?
C13 H13 0.9500 . ?
C13 C12 1.364(12) . ?
C9 H9 0.9500 . ?
C9 C10 1.359(13) . ?
C11 H11 0.9500 . ?
C11 C10 1.395(15) . ?
C11 C12 1.374(14) . ?
C10 H10 0.9500 . ?
C12 H12 0.9500 . ?
N5 C14 1.357(11) . ?
N5 C15 1.365(11) . ?
C14 H14 0.9500 . ?
C14 C18 1.372(13) . ?
C18 H18 0.9500 . ?
C18 C17 1.381(14) . ?
C15 H15 0.9500 . ?
C15 C16 1.356(13) . ?
C17 H17 0.9500 . ?
C17 C16 1.360(14) . ?
C16 H16 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.378(12) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(11) . ?
C5 C8 1.500(11) 1_556 ?
O4 C8 1.225(10) . ?
O3 C8 1.303(10) . ?
O6 H6A 0.8500 . ?
O6 H6B 0.8497 . ?
O5 H5A 0.8500 . ?
O5 H5B 0.8502 . ?
C8 C5 1.500(11) 1_554 ?

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 N4 115.9(3) . . ?
O1 Zn1 N5 103.9(3) . . ?
O1 Zn1 O3 104.0(2) . . ?
N4 Zn1 N5 112.4(3) . . ?
O3 Zn1 N4 107.7(3) . . ?
O3 Zn1 N5 112.8(3) . . ?
C7 O1 Zn1 109.7(5) . . ?
C2 C1 N1 124.2(8) . . ?
C6 C1 C2 120.7(8) . . ?
C6 C1 N1 115.1(7) . . ?
O1 C7 C3 116.0(8) . . ?
O2 C7 O1 124.3(8) . . ?
O2 C7 C3 119.7(7) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.1(8) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C7 120.3(7) . . ?
C4 C3 C7 119.3(8) . . ?
C4 C3 C2 120.3(8) . . ?
N3 N2 N1 172.3(9) . . ?
N2 N1 C1 115.4(7) . . ?
C13 N4 Zn1 121.9(6) . . ?
C13 N4 C9 116.8(8) . . ?
C9 N4 Zn1 121.2(7) . . ?
N4 C13 H13 118.2 . . ?
N4 C13 C12 123.7(9) . . ?
C12 C13 H13 118.2 . . ?
N4 C9 H9 118.5 . . ?
N4 C9 C10 122.9(9) . . ?
C10 C9 H9 118.5 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C12 C11 C10 119.0(10) . . ?
C9 C10 C11 118.9(10) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C13 C12 C11 118.7(10) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C14 N5 Zn1 124.1(6) . . ?
C14 N5 C15 115.3(8) . . ?
C15 N5 Zn1 120.3(6) . . ?
N5 C14 H14 118.5 . . ?
N5 C14 C18 123.0(9) . . ?
C18 C14 H14 118.5 . . ?
C14 C18 H18 120.1 . . ?
C14 C18 C17 119.7(9) . . ?
C17 C18 H18 120.1 . . ?
N5 C15 H15 118.1 . . ?
C16 C15 N5 123.8(9) . . ?
C16 C15 H15 118.1 . . ?
C18 C17 H17 120.9 . . ?
C16 C17 C18 118.1(10) . . ?
C16 C17 H17 120.9 . . ?
C15 C16 C17 120.0(11) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.6(8) . . ?
C5 C6 H6 120.2 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.1(8) . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.1(8) . . ?
C6 C5 C8 121.7(8) . 1_556 ?
C4 C5 C8 118.2(8) . 1_556 ?
C8 O3 Zn1 108.4(6) . . ?
H6A O6 H6B 109.5 . . ?
H5A O5 H5B 109.5 . . ?
O4 C8 C5 121.0(8) . 1_554 ?
O4 C8 O3 123.4(8) . . ?
O3 C8 C5 115.6(9) . 1_554 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13 H13 O6 0.95 2.58 3.375(12) 141.9 2_556
C9 H9 O1 0.95 2.57 3.501(11) 165.7 3_566
C14 H14 O4 0.95 2.57 3.168(12) 120.9 .
O6 H6B O5 0.85 2.12 2.925(12) 158.5 3_667
O5 H5A O2 0.85 2.11 2.930(8) 163.5 1_655
O5 H5B O6 0.85 2.05 2.886(8) 167.8 2_656

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
Zn1 O1 C7 O2 1.6(10) . . . . ?
Zn1 O1 C7 C3 -178.5(5) . . . . ?
Zn1 N4 C13 C12 179.6(7) . . . . ?
Zn1 N4 C9 C10 179.7(7) . . . . ?
Zn1 N5 C14 C18 174.0(7) . . . . ?
Zn1 N5 C15 C16 -174.3(7) . . . . ?
Zn1 O3 C8 C5 178.1(6) . . . 1_554 ?
Zn1 O3 C8 O4 -1.2(11) . . . . ?
O1 C7 C3 C2 1.7(12) . . . . ?
O1 C7 C3 C4 178.9(7) . . . . ?
O2 C7 C3 C2 -178.3(8) . . . . ?
O2 C7 C3 C4 -1.2(12) . . . . ?
C1 C2 C3 C7 -179.3(8) . . . . ?
C1 C2 C3 C4 3.6(12) . . . . ?
C1 C6 C5 C4 0.7(13) . . . . ?
C1 C6 C5 C8 -177.2(8) . . . 1_556 ?
C7 C3 C4 C5 179.5(7) . . . . ?
C2 C1 N1 N2 -1.7(13) . . . . ?
C2 C1 C6 C5 -0.5(13) . . . . ?
C2 C3 C4 C5 -3.3(13) . . . . ?
C3 C4 C5 C6 1.2(13) . . . . ?
C3 C4 C5 C8 179.2(7) . . . 1_556 ?
N1 C1 C2 C3 179.4(8) . . . . ?
N1 C1 C6 C5 178.6(8) . . . . ?
N4 C13 C12 C11 0.5(14) . . . . ?
N4 C9 C10 C11 1.0(14) . . . . ?
C13 N4 C9 C10 -1.9(12) . . . . ?
C9 N4 C13 C12 1.1(13) . . . . ?
C10 C11 C12 C13 -1.4(14) . . . . ?
C12 C11 C10 C9 0.6(14) . . . . ?
N5 C14 C18 C17 0.6(14) . . . . ?
N5 C15 C16 C17 -0.3(15) . . . . ?
C14 N5 C15 C16 0.8(13) . . . . ?
C14 C18 C17 C16 -0.1(14) . . . . ?
C18 C17 C16 C15 0.0(15) . . . . ?
C15 N5 C14 C18 -0.9(13) . . . . ?
C6 C1 C2 C3 -1.7(13) . . . . ?
C6 C1 N1 N2 179.4(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
