# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_h1-9_a
_database_code_depnum_ccdc_archive 'CCDC 1976147'
loop_
_audit_author_name
_audit_author_address
Wang
;North University of China
China
;
_audit_update_record             
;
2020-01-08 deposited with the CCDC.	2020-05-01 downloaded from the CCDC.
;
_audit_creation_date             2020-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H15 N5 O4 Zn'
_chemical_formula_sum            'C23 H15 N5 O4 Zn'
_chemical_formula_weight         490.77
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.316(6)
_cell_length_b                   12.941(3)
_cell_length_c                   13.661(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.771(5)
_cell_angle_gamma                90
_cell_volume                     4019.3(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2530
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.266
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6544
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             2000
_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  0.2380
_diffrn_reflns_av_unetI/netI     0.3278
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25305
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.993
_diffrn_reflns_theta_min         2.615
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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                1841
_reflns_number_total             4815
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.094
_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     298
_refine_ls_number_reflns         4815
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2949
_refine_ls_R_factor_gt           0.0971
_refine_ls_restrained_S_all      1.002
_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)+(0.0193P)²+10.0518P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.1216
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C18(H18), C14(H14), C21(H21), C22(H22), C15(H15), C23(H23), C4(H4),
 C3(H3), C17(H17), C20(H20), C8(H8), C11(H11), C10(H10), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.35519(3) 0.40660(5) 0.67112(5) 0.0364(2) Uani 1 1 d . . . . .
O3 O 0.41980(15) 0.4586(3) 0.7908(3) 0.0431(11) Uani 1 1 d . . . . .
N1 N 0.3994(2) 0.3041(3) 0.6168(3) 0.0360(12) Uani 1 1 d . . . . .
N4 N 0.64034(18) 0.3342(3) 0.5027(3) 0.0289(11) Uani 1 1 d . . . . .
N2 N 0.46847(19) 0.2243(3) 0.5765(3) 0.0324(12) Uani 1 1 d . . . . .
N5 N 0.65953(19) 0.4694(3) 0.4233(3) 0.0308(12) Uani 1 1 d . . . . .
C16 C 0.5238(2) 0.2035(4) 0.5653(4) 0.0285(14) Uani 1 1 d . . . . .
C19 C 0.6073(2) 0.2573(4) 0.5308(4) 0.0283(14) Uani 1 1 d . . . . .
C13 C 0.4535(2) 0.3093(4) 0.6169(4) 0.0362(16) Uani 1 1 d . . . . .
H13 H 0.478439 0.365462 0.642153 0.043 Uiso 1 1 calc R . . . .
C18 C 0.5550(2) 0.2825(4) 0.5425(4) 0.0295(14) Uani 1 1 d . . . . .
H18 H 0.541301 0.350200 0.535163 0.035 Uiso 1 1 calc R . . . .
C6 C 0.3779(2) 0.7263(5) 0.7859(4) 0.0300(14) Uani 1 1 d . . . . .
C5 C 0.3792(2) 0.6215(5) 0.8156(4) 0.0314(15) Uani 1 1 d . . . . .
C14 C 0.3788(3) 0.2100(5) 0.5727(4) 0.0419(17) Uani 1 1 d . . . . .
H14 H 0.341271 0.184585 0.561665 0.050 Uiso 1 1 calc R . . . .
C21 C 0.6184(2) 0.4143(4) 0.4390(4) 0.0300(14) Uani 1 1 d . . . . .
H21 H 0.578478 0.429150 0.409212 0.036 Uiso 1 1 calc R . . . .
N3 N 0.5955(2) 0.0793(4) 0.5646(4) 0.0603(16) Uani 1 1 d . . . . .
O4 O 0.48004(18) 0.5823(4) 0.8705(4) 0.0973(19) Uani 1 1 d . . . . .
C22 C 0.7006(2) 0.3393(5) 0.5303(4) 0.0367(15) Uani 1 1 d . . . . .
H22 H 0.728041 0.293784 0.573846 0.044 Uiso 1 1 calc R . . . .
C15 C 0.4202(3) 0.1599(4) 0.5478(4) 0.0444(17) Uani 1 1 d . . . . .
H15 H 0.417040 0.094872 0.517252 0.053 Uiso 1 1 calc R . . . .
C2 C 0.2853(2) 0.7463(5) 0.8171(4) 0.0385(16) Uani 1 1 d . . . . .
C23 C 0.7118(2) 0.4231(5) 0.4820(4) 0.0408(16) Uani 1 1 d . . . . .
H23 H 0.749025 0.446017 0.487423 0.049 Uiso 1 1 calc R . . . .
C4 C 0.3333(2) 0.5815(5) 0.8388(4) 0.0406(16) Uani 1 1 d . . . . .
H4 H 0.332996 0.511384 0.853711 0.049 Uiso 1 1 calc R . . . .
C7 C 0.3297(2) 0.7890(5) 0.7861(4) 0.0351(15) Uani 1 1 d . . . . .
O1 O 0.1885(2) 0.8119(6) 0.7641(4) 0.130(3) Uani 1 1 d . . . . .
C12 C 0.4301(3) 0.5497(6) 0.8260(5) 0.0453(18) Uani 1 1 d . . . . .
C3 C 0.2867(3) 0.6443(5) 0.8405(5) 0.0485(18) Uani 1 1 d . . . . .
H3 H 0.256245 0.615659 0.857810 0.058 Uiso 1 1 calc R . . . .
C17 C 0.5453(3) 0.1044(5) 0.5777(4) 0.0481(17) Uani 1 1 d . . . . .
H17 H 0.524047 0.052815 0.595931 0.058 Uiso 1 1 calc R . . . .
C20 C 0.6254(3) 0.1555(5) 0.5416(5) 0.0507(18) Uani 1 1 d . . . . .
H20 H 0.660428 0.139337 0.532186 0.061 Uiso 1 1 calc R . . . .
C8 C 0.3281(3) 0.8924(6) 0.7545(4) 0.0556(18) Uani 1 1 d . . . . .
H8 H 0.297268 0.934255 0.755728 0.067 Uiso 1 1 calc R . . . .
C1 C 0.2352(4) 0.8142(6) 0.8253(7) 0.062(2) Uani 1 1 d . . . . .
C11 C 0.4213(3) 0.7718(6) 0.7532(5) 0.0553(19) Uani 1 1 d . . . . .
H11 H 0.453255 0.732298 0.753176 0.066 Uiso 1 1 calc R . . . .
C10 C 0.4173(3) 0.8717(7) 0.7217(5) 0.069(2) Uani 1 1 d . . . . .
H10 H 0.446263 0.899625 0.699697 0.083 Uiso 1 1 calc R . . . .
C9 C 0.3701(3) 0.9331(5) 0.7220(5) 0.071(2) Uani 1 1 d . . . . .
H9 H 0.367509 1.001510 0.700076 0.085 Uiso 1 1 calc R . . . .
O2 O 0.2450(3) 0.8663(6) 0.8997(6) 0.195(4) 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 O3 1.942(4) . ?
Zn1 N1 2.007(4) . ?
Zn1 N5 2.010(4) 5_666 ?
Zn1 O1 2.021(5) 4_546 ?
Zn1 C1 2.517(8) 4_546 ?
Zn1 O2 2.340(6) 4_546 ?
O3 C12 1.264(6) . ?
N1 C13 1.318(6) . ?
N1 C14 1.372(6) . ?
N4 C19 1.415(6) . ?
N4 C21 1.338(6) . ?
N4 C22 1.378(6) . ?
N2 C16 1.433(6) . ?
N2 C13 1.338(6) . ?
N2 C15 1.378(6) . ?
N5 C21 1.306(6) . ?
N5 C23 1.377(6) . ?
C16 C18 1.372(6) . ?
C16 C17 1.372(7) . ?
C19 C18 1.376(6) . ?
C19 C20 1.380(7) . ?
C13 H13 0.9300 . ?
C18 H18 0.9300 . ?
C6 C5 1.412(7) . ?
C6 C7 1.427(7) . ?
C6 C11 1.411(7) . ?
C5 C4 1.366(7) . ?
C5 C12 1.514(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.340(7) . ?
C21 H21 0.9300 . ?
N3 C17 1.335(6) . ?
N3 C20 1.327(7) . ?
O4 C12 1.224(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.347(7) . ?
C15 H15 0.9300 . ?
C2 C7 1.405(7) . ?
C2 C3 1.355(7) . ?
C2 C1 1.538(9) . ?
C23 H23 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.403(7) . ?
C7 C8 1.402(8) . ?
O1 C1 1.147(8) . ?
C3 H3 0.9300 . ?
C17 H17 0.9300 . ?
C20 H20 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.356(8) . ?
C1 O2 1.172(8) . ?
C11 H11 0.9300 . ?
C11 C10 1.356(8) . ?
C10 H10 0.9300 . ?
C10 C9 1.398(9) . ?
C9 H9 0.9300 . ?

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
O3 Zn1 N1 99.25(17) . . ?
O3 Zn1 N5 99.79(17) . 5_666 ?
O3 Zn1 O1 103.6(2) . 4_546 ?
O3 Zn1 C1 126.8(2) . 4_546 ?
O3 Zn1 O2 147.0(2) . 4_546 ?
N1 Zn1 N5 106.69(18) . 5_666 ?
N1 Zn1 O1 101.2(2) . 4_546 ?
N1 Zn1 C1 106.2(2) . 4_546 ?
N1 Zn1 O2 108.4(3) . 4_546 ?
N5 Zn1 O1 139.8(2) 5_666 4_546 ?
N5 Zn1 C1 115.7(2) 5_666 4_546 ?
N5 Zn1 O2 89.4(2) 5_666 4_546 ?
O1 Zn1 C1 26.5(2) 4_546 4_546 ?
O1 Zn1 O2 54.1(2) 4_546 4_546 ?
O2 Zn1 C1 27.61(19) 4_546 4_546 ?
C12 O3 Zn1 129.4(4) . . ?
C13 N1 Zn1 129.2(4) . . ?
C13 N1 C14 104.8(5) . . ?
C14 N1 Zn1 126.0(4) . . ?
C21 N4 C19 126.0(5) . . ?
C21 N4 C22 106.3(4) . . ?
C22 N4 C19 127.6(5) . . ?
C13 N2 C16 127.0(5) . . ?
C13 N2 C15 106.7(5) . . ?
C15 N2 C16 126.4(5) . . ?
C21 N5 Zn1 124.6(4) . 5_666 ?
C21 N5 C23 105.6(5) . . ?
C23 N5 Zn1 129.7(4) . 5_666 ?
C18 C16 N2 119.9(5) . . ?
C17 C16 N2 119.5(5) . . ?
C17 C16 C18 120.5(5) . . ?
C18 C19 N4 120.1(5) . . ?
C18 C19 C20 119.1(5) . . ?
C20 C19 N4 120.7(5) . . ?
N1 C13 N2 112.0(5) . . ?
N1 C13 H13 124.0 . . ?
N2 C13 H13 124.0 . . ?
C16 C18 C19 117.2(5) . . ?
C16 C18 H18 121.4 . . ?
C19 C18 H18 121.4 . . ?
C5 C6 C7 118.7(5) . . ?
C11 C6 C5 123.3(6) . . ?
C11 C6 C7 118.1(6) . . ?
C6 C5 C12 123.4(5) . . ?
C4 C5 C6 119.7(5) . . ?
C4 C5 C12 116.9(6) . . ?
N1 C14 H14 124.7 . . ?
C15 C14 N1 110.5(5) . . ?
C15 C14 H14 124.7 . . ?
N4 C21 H21 123.9 . . ?
N5 C21 N4 112.2(5) . . ?
N5 C21 H21 123.9 . . ?
C20 N3 C17 117.1(5) . . ?
N4 C22 H22 126.7 . . ?
C23 C22 N4 106.6(5) . . ?
C23 C22 H22 126.7 . . ?
N2 C15 H15 127.0 . . ?
C14 C15 N2 106.0(5) . . ?
C14 C15 H15 127.0 . . ?
C7 C2 C1 120.7(6) . . ?
C3 C2 C7 119.8(6) . . ?
C3 C2 C1 119.5(6) . . ?
N5 C23 H23 125.4 . . ?
C22 C23 N5 109.2(5) . . ?
C22 C23 H23 125.4 . . ?
C5 C4 H4 119.5 . . ?
C5 C4 C3 121.0(6) . . ?
C3 C4 H4 119.5 . . ?
C2 C7 C6 119.8(6) . . ?
C8 C7 C6 118.4(6) . . ?
C8 C7 C2 121.8(6) . . ?
C1 O1 Zn1 101.7(6) . 4_556 ?
O3 C12 C5 119.5(6) . . ?
O4 C12 O3 122.5(6) . . ?
O4 C12 C5 118.0(6) . . ?
C2 C3 C4 120.9(6) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C16 C17 H17 118.8 . . ?
N3 C17 C16 122.4(6) . . ?
N3 C17 H17 118.8 . . ?
C19 C20 H20 118.2 . . ?
N3 C20 C19 123.6(5) . . ?
N3 C20 H20 118.2 . . ?
C7 C8 H8 119.0 . . ?
C9 C8 C7 122.0(7) . . ?
C9 C8 H8 119.0 . . ?
C2 C1 Zn1 172.9(6) . 4_556 ?
O1 C1 Zn1 51.8(5) . 4_556 ?
O1 C1 C2 122.4(8) . . ?
O1 C1 O2 119.5(9) . . ?
O2 C1 Zn1 67.7(5) . 4_556 ?
O2 C1 C2 117.9(8) . . ?
C6 C11 H11 119.3 . . ?
C10 C11 C6 121.4(6) . . ?
C10 C11 H11 119.3 . . ?
C11 C10 H10 119.8 . . ?
C11 C10 C9 120.4(7) . . ?
C9 C10 H10 119.8 . . ?
C8 C9 C10 119.7(7) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C1 O2 Zn1 84.7(5) . 4_556 ?

_olex2_submission_special_instructions 'No special instructions were received'
