# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1d
_database_code_depnum_ccdc_archive 'CCDC 1899157'
loop_
_audit_author_name
_audit_author_address
'Yu-Xiao Zhang'
;Chinese Academy of Science
China
;
_audit_update_record             
;
2019-02-24 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;
_audit_creation_date             2019-02-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 N3 O6 Zn'
_chemical_formula_sum            'C16 H13 N3 O6 Zn'
_chemical_formula_weight         408.66
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   4.9797(4)
_cell_length_b                   11.2729(11)
_cell_length_c                   27.335(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1534.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4407
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      2.2352
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.644
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       platy
_exptl_crystal_F_000             832
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0820
_diffrn_reflns_av_unetI/netI     0.1063
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            13295
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_min         2.874
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2406
_reflns_number_total             3519
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 
;
 Flack x determined using 638 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.057(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3519
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      0.880
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0218P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0735
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Rotating group:
 O5W(H5WA,H5WB), O6W(H6WA)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15)
;
_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 -0.98884(13) 1.04316(5) -0.07340(2) 0.02839(16) Uani 1 1 d . . . . .
N1 N 0.2752(8) 0.9454(4) 0.17286(14) 0.0277(10) Uani 1 1 d . . . . .
N2 N 0.4060(9) 0.7605(4) 0.17509(15) 0.0327(12) Uani 1 1 d . . . . .
H2 H 0.493232 0.698138 0.183755 0.039 Uiso 1 1 calc R . . . .
N3 N 0.2135(9) 0.7632(3) 0.14013(15) 0.0304(11) Uani 1 1 d . . . . .
C1 C -0.6659(9) 1.0445(5) 0.00498(18) 0.0268(11) Uani 1 1 d . . . . .
C2 C -0.4630(11) 1.0018(4) 0.04170(17) 0.0251(12) Uani 1 1 d . . . . .
C3 C -0.3166(10) 1.0804(4) 0.0698(2) 0.0336(14) Uani 1 1 d . . . . .
H3 H -0.351116 1.161245 0.067290 0.040 Uiso 1 1 calc R . . . .
C4 C -0.1191(9) 1.0409(4) 0.10154(18) 0.0293(12) Uani 1 1 d . . . . .
H4 H -0.020470 1.095574 0.119580 0.035 Uiso 1 1 calc R . . . .
C5 C -0.0670(9) 0.9208(4) 0.10676(18) 0.0244(12) Uani 1 1 d . . . . .
C6 C -0.2184(11) 0.8414(4) 0.0785(2) 0.0330(14) Uani 1 1 d . . . . .
H6 H -0.186471 0.760385 0.081235 0.040 Uiso 1 1 calc R . . . .
C7 C -0.4136(10) 0.8810(4) 0.04657(18) 0.0285(13) Uani 1 1 d . . . . .
H7 H -0.512376 0.826724 0.028301 0.034 Uiso 1 1 calc R . . . .
C8 C 0.1386(9) 0.8775(4) 0.13988(18) 0.0252(12) Uani 1 1 d . . . . .
C9 C 0.4416(10) 0.8689(4) 0.19433(18) 0.0243(12) Uani 1 1 d . . . . .
C10 C 0.6317(10) 0.8914(4) 0.23357(19) 0.0273(13) Uani 1 1 d . . . . .
C11 C 0.7409(10) 1.0033(4) 0.23998(19) 0.0291(13) Uani 1 1 d . . . . .
H11 H 0.688164 1.065276 0.219692 0.035 Uiso 1 1 calc R . . . .
C12 C 0.9286(10) 1.0232(4) 0.27648(18) 0.0327(14) Uani 1 1 d . . . . .
H12 H 1.005512 1.097990 0.279738 0.039 Uiso 1 1 calc R . . . .
C13 C 1.0028(11) 0.9335(4) 0.30809(16) 0.0256(10) Uani 1 1 d . . . . .
C14 C 0.8909(11) 0.8226(4) 0.3021(2) 0.0368(15) Uani 1 1 d . . . . .
H14 H 0.939629 0.761331 0.323063 0.044 Uiso 1 1 calc R . . . .
C16 C 1.1994(10) 0.9566(5) 0.34800(19) 0.0294(12) Uani 1 1 d . . . . .
C15 C 0.7078(11) 0.8013(4) 0.2653(2) 0.0374(15) Uani 1 1 d . . . . .
H15 H 0.634493 0.725934 0.261758 0.045 Uiso 1 1 calc R . . . .
O2 O -0.7547(7) 1.1469(3) 0.00463(13) 0.0355(10) Uani 1 1 d . . . . .
O1 O -0.7395(7) 0.9671(3) -0.02732(12) 0.0289(8) Uani 1 1 d . . . . .
O3 O 1.2231(7) 0.8772(3) 0.38154(13) 0.0328(9) Uani 1 1 d . . . . .
O4 O 1.3327(7) 1.0493(3) 0.34981(13) 0.0425(10) Uani 1 1 d . . . . .
O5W O -1.2732(7) 0.9195(3) -0.07660(14) 0.0416(10) Uani 1 1 d . . . . .
H5WA H -1.290525 0.895384 -0.106191 0.062 Uiso 1 1 d GR . . . .
H5WB H -1.425547 0.950951 -0.069899 0.062 Uiso 1 1 d GR . . . .
O6W O -1.2511(8) 1.1737(3) -0.06665(18) 0.0383(11) Uani 1 1 d . . . . .
H6WA H -1.405211 1.150192 -0.076329 0.057 Uiso 1 1 d GR . . . .
H6WB H -1.243(15) 1.222(5) -0.048(2) 0.07(3) 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 C16 2.587(5) 2_574 ?
Zn1 O1 1.966(3) . ?
Zn1 O3 2.019(3) 2_574 ?
Zn1 O4 2.469(4) 2_574 ?
Zn1 O5W 1.989(3) . ?
Zn1 O6W 1.976(4) . ?
N1 C8 1.364(6) . ?
N1 C9 1.332(6) . ?
N2 H2 0.8600 . ?
N2 N3 1.354(5) . ?
N2 C9 1.342(5) . ?
N3 C8 1.342(6) . ?
C1 C2 1.503(7) . ?
C1 O2 1.237(6) . ?
C1 O1 1.294(5) . ?
C2 C3 1.380(6) . ?
C2 C7 1.390(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(6) . ?
C5 C6 1.403(6) . ?
C5 C8 1.451(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(6) . ?
C7 H7 0.9300 . ?
C9 C10 1.453(6) . ?
C10 C11 1.385(6) . ?
C10 C15 1.389(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(6) . ?
C13 C14 1.379(6) . ?
C13 C16 1.489(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(7) . ?
C16 O3 1.287(6) . ?
C16 O4 1.239(6) . ?
C15 H15 0.9300 . ?
O5W H5WA 0.8575 . ?
O5W H5WB 0.8575 . ?
O6W H6WA 0.8538 . ?
O6W H6WB 0.75(5) . ?

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 C16 100.41(14) . 2_574 ?
O1 Zn1 O3 99.84(14) . 2_574 ?
O1 Zn1 O4 99.31(13) . 2_574 ?
O1 Zn1 O5W 99.90(14) . . ?
O1 Zn1 O6W 133.05(17) . . ?
O3 Zn1 C16 29.26(14) 2_574 2_574 ?
O3 Zn1 O4 57.49(13) 2_574 2_574 ?
O4 Zn1 C16 28.24(13) 2_574 2_574 ?
O5W Zn1 C16 111.14(17) . 2_574 ?
O5W Zn1 O3 138.72(16) . 2_574 ?
O5W Zn1 O4 83.73(14) . 2_574 ?
O6W Zn1 C16 116.42(18) . 2_574 ?
O6W Zn1 O3 99.15(16) . 2_574 ?
O6W Zn1 O4 126.99(16) . 2_574 ?
O6W Zn1 O5W 93.19(15) . . ?
C9 N1 C8 103.8(4) . . ?
N3 N2 H2 124.8 . . ?
C9 N2 H2 124.8 . . ?
C9 N2 N3 110.5(4) . . ?
C8 N3 N2 102.8(4) . . ?
O2 C1 C2 123.0(5) . . ?
O2 C1 O1 121.5(5) . . ?
O1 C1 C2 115.4(4) . . ?
C3 C2 C1 121.3(4) . . ?
C3 C2 C7 118.9(5) . . ?
C7 C2 C1 119.8(5) . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.1(5) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.8(5) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 117.7(5) . . ?
C4 C5 C8 121.6(4) . . ?
C6 C5 C8 120.6(4) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.4(4) . . ?
C7 C6 H6 119.3 . . ?
C2 C7 H7 119.9 . . ?
C6 C7 C2 120.1(5) . . ?
C6 C7 H7 119.9 . . ?
N1 C8 C5 125.2(5) . . ?
N3 C8 N1 113.4(4) . . ?
N3 C8 C5 121.5(5) . . ?
N1 C9 N2 109.5(4) . . ?
N1 C9 C10 128.2(4) . . ?
N2 C9 C10 122.3(4) . . ?
C11 C10 C9 120.5(5) . . ?
C11 C10 C15 118.7(5) . . ?
C15 C10 C9 120.8(5) . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.3(5) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(5) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C16 120.4(5) . . ?
C14 C13 C12 118.8(5) . . ?
C14 C13 C16 120.8(5) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.8(5) . . ?
C15 C14 H14 119.6 . . ?
C13 C16 Zn1 167.1(4) . 2_575 ?
O3 C16 Zn1 50.1(2) . 2_575 ?
O3 C16 C13 117.4(5) . . ?
O4 C16 Zn1 70.6(3) . 2_575 ?
O4 C16 C13 122.0(5) . . ?
O4 C16 O3 120.6(5) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.6(5) . . ?
C14 C15 H15 119.7 . . ?
C1 O1 Zn1 108.8(3) . . ?
C16 O3 Zn1 100.7(3) . 2_575 ?
C16 O4 Zn1 81.2(3) . 2_575 ?
Zn1 O5W H5WA 109.6 . . ?
Zn1 O5W H5WB 109.3 . . ?
H5WA O5W H5WB 104.1 . . ?
Zn1 O6W H6WA 109.5 . . ?
Zn1 O6W H6WB 124(6) . . ?
H6WA O6W H6WB 119.2 . . ?

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
_geom_hbond_publ_flag
N2 H2 O4 0.86 2.10 2.798(6) 137.9 4_745 yes
O5W H5WA N3 0.86 2.01 2.694(5) 135.6 3_365 yes
O5W H5WB O1 0.86 1.96 2.738(5) 150.7 1_455 yes
O6W H6WA O3 0.85 1.98 2.803(5) 161.1 2_474 yes
O6W H6WB O2 0.75(5) 1.89(5) 2.639(5) 173(7) 3_475 yes

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
N1 C9 C10 C11 -27.1(8) . . . . ?
N1 C9 C10 C15 153.1(6) . . . . ?
N2 N3 C8 N1 0.0(6) . . . . ?
N2 N3 C8 C5 179.5(4) . . . . ?
N2 C9 C10 C11 154.9(5) . . . . ?
N2 C9 C10 C15 -25.0(8) . . . . ?
N3 N2 C9 N1 0.1(6) . . . . ?
N3 N2 C9 C10 178.4(4) . . . . ?
C1 C2 C3 C4 -176.3(5) . . . . ?
C1 C2 C7 C6 176.8(5) . . . . ?
C2 C1 O1 Zn1 -177.1(3) . . . . ?
C2 C3 C4 C5 -1.3(8) . . . . ?
C3 C2 C7 C6 -1.0(8) . . . . ?
C3 C4 C5 C6 0.7(8) . . . . ?
C3 C4 C5 C8 -179.9(5) . . . . ?
C4 C5 C6 C7 -0.2(8) . . . . ?
C4 C5 C8 N1 8.5(8) . . . . ?
C4 C5 C8 N3 -171.0(5) . . . . ?
C5 C6 C7 C2 0.4(8) . . . . ?
C6 C5 C8 N1 -172.2(5) . . . . ?
C6 C5 C8 N3 8.4(7) . . . . ?
C7 C2 C3 C4 1.5(8) . . . . ?
C8 N1 C9 N2 0.0(5) . . . . ?
C8 N1 C9 C10 -178.3(5) . . . . ?
C8 C5 C6 C7 -179.6(5) . . . . ?
C9 N1 C8 N3 0.0(6) . . . . ?
C9 N1 C8 C5 -179.5(5) . . . . ?
C9 N2 N3 C8 -0.1(5) . . . . ?
C9 C10 C11 C12 -177.9(5) . . . . ?
C9 C10 C15 C14 179.1(5) . . . . ?
C10 C11 C12 C13 -2.3(8) . . . . ?
C11 C10 C15 C14 -0.8(8) . . . . ?
C11 C12 C13 C14 1.3(8) . . . . ?
C11 C12 C13 C16 -178.4(5) . . . . ?
C12 C13 C14 C15 -0.2(8) . . . . ?
C12 C13 C16 Zn1 155.7(14) . . . 2_575 ?
C12 C13 C16 O3 167.4(5) . . . . ?
C12 C13 C16 O4 -11.3(8) . . . . ?
C13 C14 C15 C10 -0.1(9) . . . . ?
C13 C16 O3 Zn1 -176.6(4) . . . 2_575 ?
C13 C16 O4 Zn1 177.0(5) . . . 2_575 ?
C14 C13 C16 Zn1 -24(2) . . . 2_575 ?
C14 C13 C16 O3 -12.4(8) . . . . ?
C14 C13 C16 O4 168.9(5) . . . . ?
C16 C13 C14 C15 179.6(5) . . . . ?
C15 C10 C11 C12 2.0(8) . . . . ?
O2 C1 C2 C3 -15.6(8) . . . . ?
O2 C1 C2 C7 166.7(5) . . . . ?
O2 C1 O1 Zn1 1.7(6) . . . . ?
O1 C1 C2 C3 163.1(5) . . . . ?
O1 C1 C2 C7 -14.6(7) . . . . ?
O3 C16 O4 Zn1 -1.7(4) . . . 2_575 ?
O4 C16 O3 Zn1 2.1(6) . . . 2_575 ?

_olex2_submission_special_instructions 'No special instructions were received'
