# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_220425a
_audit_block_doi                 10.5517/ccdc.csd.cc2h45f8
_database_code_depnum_ccdc_archive 'CCDC 2297919'
loop_
_audit_author_name
_audit_author_address
'Xiaoxue Ma'
;Liaocheng University
China
;
_audit_update_record             
;
2023-09-28 deposited with the CCDC.	2024-04-12 downloaded from the CCDC.
;
_audit_creation_date             2023-09-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C7.385 H4.308 N3.692 Ni0.308 O2.462'
_chemical_formula_sum            'C7.38 H3.69 N3.69 Ni0.31 O2.46'
_chemical_formula_weight         201.59
_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'
Ni Ni 0.3393 1.1124 '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           57
_space_group_name_H-M_alt        'P b c m'
_space_group_name_Hall           '-P 2c 2b'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z-1/2'
'-x, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.2370(8)
_cell_length_b                   20.4549(19)
_cell_length_c                   24.962(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3695.2(6)
_cell_formula_units_Z            13
_cell_measurement_reflns_used    3608
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.033
_cell_measurement_theta_min      2.617
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.579
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2313
_diffrn_reflns_av_unetI/netI     0.1333
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14614
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        23.255
_diffrn_reflns_theta_max         23.255
_diffrn_reflns_theta_min         1.991
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1545
_reflns_number_total             2719
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 v6.02A (Bruker, 2001)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v6.02A (Bruker, 2001)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.054
_refine_diff_density_min         -0.842
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1601
_refine_ls_R_factor_gt           0.1072
_refine_ls_restrained_S_all      1.119
_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)+(0.1304P)²+13.9636P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2625
_refine_ls_wR_factor_ref         0.2932
_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) groups
2. Restrained distances
 C18-C23
 1.34 with sigma of 0.01
 C8-C12
 1.34 with sigma of 0.01
3.a Fixed occupancy and ADP/Uiso:
 Ni1, N1, O2, N2, O4
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C10(H10), C14(H14), C16(H16), C17(H17), C19(H19), C21(H21), C1(H1)
3.c Idealised tetrahedral OH refined as rotating group:
 O20(H20)
;
_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
Ni1 Ni 0.000000 0.500000 0.000000 0.031 Uani 1 2 d S . P . .
N1 N 0.2373(10) 0.4453(3) -0.0182(3) 0.035 Uani 1 1 d . . . . .
O2 O 0.8353(9) 0.4159(3) -0.0017(2) 0.038 Uani 1 1 d . . . . .
N2 N 0.4360(11) 0.3651(3) -0.0246(3) 0.038 Uani 1 1 d . . . . .
O4 O 0.9445(10) 0.3602(3) -0.0727(3) 0.052 Uani 1 1 d . . . . .
C5 C 0.077(2) 0.4147(6) 0.250000 0.039(3) Uani 1 2 d S T P . .
H5 H 0.096863 0.459623 0.250000 0.046 Uiso 1 2 calc R U P . .
N3 N 0.4733(13) 0.4031(4) -0.0670(4) 0.070(3) Uani 1 1 d . . . . .
N4 N 0.0485(11) 0.4760(4) 0.0801(3) 0.0380(19) Uani 1 1 d . . . . .
C8 C 0.8404(12) 0.3640(3) -0.0312(4) 0.034(2) Uani 1 1 d D . . . .
N5 N 0.0868(12) 0.4215(4) 0.1547(3) 0.043(2) Uani 1 1 d . . . . .
C10 C 0.823(2) 0.250000 0.000000 0.041(3) Uani 1 2 d S T P . .
H10 H 0.951370 0.250001 0.000002 0.050 Uiso 1 2 calc R U P . .
O11 O 0.1159(14) 0.2902(4) 0.1077(3) 0.084(3) Uani 1 1 d . . . . .
C12 C 0.7353(12) 0.3085(3) -0.0160(3) 0.032(2) Uani 1 1 d D . . . .
C14 C 0.007(2) 0.2817(8) 0.250000 0.061(5) Uani 1 2 d S T P . .
H14 H -0.018206 0.237091 0.250000 0.073 Uiso 1 2 calc R U P . .
C15 C 0.5401(12) 0.3068(4) -0.0138(4) 0.033(2) Uani 1 1 d . . . . .
C16 C 0.2991(13) 0.3905(4) 0.0029(4) 0.045(2) Uani 1 1 d . . . . .
H16 H 0.251135 0.371923 0.033914 0.053 Uiso 1 1 calc R U . . .
C17 C 0.3489(17) 0.4504(5) -0.0613(5) 0.065(3) Uani 1 1 d . . . . .
H17 H 0.339367 0.484819 -0.085462 0.079 Uiso 1 1 calc R U . . .
C18 C 0.0252(15) 0.3130(5) 0.1986(4) 0.051(3) Uani 1 1 d D . . . .
C19 C 0.4452(17) 0.250000 0.000000 0.038(3) Uani 1 2 d S T P . .
H19 H 0.316724 0.250000 0.000001 0.045 Uiso 1 2 calc R U P . .
O20 O -0.0702(16) 0.2209(4) 0.1515(4) 0.095(3) Uani 1 1 d . . . . .
H20 H -0.070207 0.204632 0.121468 0.142 Uiso 1 1 calc R U . . .
C21 C -0.0186(15) 0.4267(5) 0.1107(4) 0.049(3) Uani 1 1 d . . . . .
H21 H -0.120385 0.400769 0.102508 0.059 Uiso 1 1 calc R U . . .
C22 C 0.0620(15) 0.3817(5) 0.2027(4) 0.045(3) Uani 1 1 d . . . . .
C23 C 0.0297(18) 0.2772(5) 0.1509(4) 0.063(3) Uani 1 1 d D . . . .
C1 C 0.1917(15) 0.4999(5) 0.1087(4) 0.052(3) Uani 1 1 d . . . . .
H1 H 0.263284 0.535060 0.097395 0.062 Uiso 1 1 calc R U . . .
N6 N 0.2213(13) 0.4678(4) 0.1554(3) 0.054(3) 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
Ni1 N1 2.099(7) . ?
Ni1 N1 2.099(7) 5_565 ?
Ni1 O2 2.093(6) 5_665 ?
Ni1 O2 2.093(6) 1_455 ?
Ni1 N4 2.089(7) 5_565 ?
Ni1 N4 2.089(7) . ?
N1 C16 1.317(11) . ?
N1 C17 1.349(13) . ?
O2 C8 1.293(9) . ?
N2 N3 1.342(11) . ?
N2 C15 1.436(11) . ?
N2 C16 1.313(11) . ?
O4 C8 1.283(10) . ?
C5 H5 0.9300 . ?
C5 C22 1.365(11) . ?
C5 C22 1.365(11) 6_556 ?
N3 C17 1.330(13) . ?
N4 C21 1.354(12) . ?
N4 C1 1.351(12) . ?
C8 C12 1.418(8) . ?
N5 C21 1.343(12) . ?
N5 C22 1.460(12) . ?
N5 N6 1.358(10) . ?
C10 H10 0.9300 . ?
C10 C12 1.412(10) 3 ?
C10 C12 1.412(10) . ?
O11 C23 1.273(13) . ?
C12 C15 1.414(12) . ?
C14 H14 0.9300 . ?
C14 C18 1.439(12) 6_556 ?
C14 C18 1.439(12) . ?
C15 C19 1.392(11) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C22 1.433(13) . ?
C18 C23 1.400(9) . ?
C19 H19 0.9300 . ?
O20 H20 0.8200 . ?
O20 C23 1.359(13) . ?
C21 H21 0.9300 . ?
C1 H1 0.9300 . ?
C1 N6 1.357(12) . ?

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 Ni1 N1 180.0 . 5_565 ?
O2 Ni1 N1 88.6(2) 1_455 5_565 ?
O2 Ni1 N1 91.4(2) 1_455 . ?
O2 Ni1 N1 91.4(2) 5_665 5_565 ?
O2 Ni1 N1 88.6(2) 5_665 . ?
O2 Ni1 O2 180.0(3) 5_665 1_455 ?
N4 Ni1 N1 86.8(3) . . ?
N4 Ni1 N1 93.2(3) . 5_565 ?
N4 Ni1 N1 93.2(3) 5_565 . ?
N4 Ni1 N1 86.8(3) 5_565 5_565 ?
N4 Ni1 O2 85.5(3) . 1_455 ?
N4 Ni1 O2 94.5(3) 5_565 1_455 ?
N4 Ni1 O2 85.5(3) 5_565 5_665 ?
N4 Ni1 O2 94.5(3) . 5_665 ?
N4 Ni1 N4 180.0 5_565 . ?
C16 N1 Ni1 130.2(7) . . ?
C16 N1 C17 100.4(8) . . ?
C17 N1 Ni1 128.4(6) . . ?
C8 O2 Ni1 132.1(5) . 1_655 ?
N3 N2 C15 121.6(8) . . ?
C16 N2 N3 109.5(8) . . ?
C16 N2 C15 128.8(8) . . ?
C22 C5 H5 120.1 6_556 . ?
C22 C5 H5 120.1 . . ?
C22 C5 C22 119.8(12) 6_556 . ?
C17 N3 N2 101.5(8) . . ?
C21 N4 Ni1 130.9(7) . . ?
C1 N4 Ni1 123.3(6) . . ?
C1 N4 C21 104.3(8) . . ?
O2 C8 C12 119.4(8) . . ?
O4 C8 O2 121.7(7) . . ?
O4 C8 C12 118.8(7) . . ?
C21 N5 C22 130.3(9) . . ?
C21 N5 N6 111.3(8) . . ?
N6 N5 C22 117.8(8) . . ?
C12 C10 H10 116.7 3 . ?
C12 C10 H10 116.7 . . ?
C12 C10 C12 126.6(12) . 3 ?
C10 C12 C8 120.9(9) . . ?
C10 C12 C15 114.6(8) . . ?
C15 C12 C8 124.5(8) . . ?
C18 C14 H14 117.0 . . ?
C18 C14 H14 117.0 6_556 . ?
C18 C14 C18 125.9(14) 6_556 . ?
C12 C15 N2 119.7(8) . . ?
C19 C15 N2 118.7(8) . . ?
C19 C15 C12 121.6(8) . . ?
N1 C16 H16 123.7 . . ?
N2 C16 N1 112.7(9) . . ?
N2 C16 H16 123.7 . . ?
N1 C17 H17 122.1 . . ?
N3 C17 N1 115.8(9) . . ?
N3 C17 H17 122.1 . . ?
C22 C18 C14 113.0(9) . . ?
C23 C18 C14 121.8(11) . . ?
C23 C18 C22 124.7(10) . . ?
C15 C19 C15 120.9(11) 3 . ?
C15 C19 H19 119.6 3 . ?
C15 C19 H19 119.6 . . ?
C23 O20 H20 109.5 . . ?
N4 C21 H21 125.8 . . ?
N5 C21 N4 108.4(9) . . ?
N5 C21 H21 125.8 . . ?
C5 C22 N5 115.0(9) . . ?
C5 C22 C18 124.2(9) . . ?
C18 C22 N5 120.8(8) . . ?
O11 C23 C18 128.5(11) . . ?
O11 C23 O20 116.6(9) . . ?
O20 C23 C18 114.9(10) . . ?
N4 C1 H1 123.2 . . ?
N4 C1 N6 113.6(9) . . ?
N6 C1 H1 123.2 . . ?
C1 N6 N5 102.3(8) . . ?

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
Ni1 N1 C16 N2 169.5(6) . . . . ?
Ni1 N1 C17 N3 -170.0(8) . . . . ?
Ni1 O2 C8 O4 -10.2(13) 1_655 . . . ?
Ni1 O2 C8 C12 166.7(6) 1_655 . . . ?
Ni1 N4 C21 N5 164.5(6) . . . . ?
Ni1 N4 C1 N6 -166.4(7) . . . . ?
O2 C8 C12 C10 -113.3(9) . . . . ?
O2 C8 C12 C15 64.6(13) . . . . ?
N2 N3 C17 N1 0.6(14) . . . . ?
N2 C15 C19 C15 -176.4(9) . . . 3 ?
O4 C8 C12 C10 63.7(11) . . . . ?
O4 C8 C12 C15 -118.4(10) . . . . ?
N3 N2 C15 C12 46.7(13) . . . . ?
N3 N2 C15 C19 -134.8(9) . . . . ?
N3 N2 C16 N1 -0.1(12) . . . . ?
N4 C1 N6 N5 0.0(11) . . . . ?
C8 C12 C15 N2 -3.4(14) . . . . ?
C8 C12 C15 C19 178.1(7) . . . . ?
C10 C12 C15 N2 174.6(6) . . . . ?
C10 C12 C15 C19 -3.9(12) . . . . ?
C12 C10 C12 C8 180.0(9) 3 . . . ?
C12 C10 C12 C15 1.9(6) 3 . . . ?
C12 C15 C19 C15 2.1(6) . . . 3 ?
C14 C18 C22 C5 -0.7(18) . . . . ?
C14 C18 C22 N5 179.3(11) . . . . ?
C14 C18 C23 O11 -147.9(14) . . . . ?
C14 C18 C23 O20 31.4(18) . . . . ?
C15 N2 N3 C17 -179.3(9) . . . . ?
C15 N2 C16 N1 178.9(8) . . . . ?
C16 N1 C17 N3 -0.6(13) . . . . ?
C16 N2 N3 C17 -0.3(12) . . . . ?
C16 N2 C15 C12 -132.1(10) . . . . ?
C16 N2 C15 C19 46.4(13) . . . . ?
C17 N1 C16 N2 0.4(11) . . . . ?
C18 C14 C18 C22 -1(2) 6_556 . . . ?
C18 C14 C18 C23 171.4(12) 6_556 . . . ?
C21 N4 C1 N6 1.0(11) . . . . ?
C21 N5 C22 C5 -129.6(12) . . . . ?
C21 N5 C22 C18 50.4(15) . . . . ?
C21 N5 N6 C1 -1.1(11) . . . . ?
C22 C5 C22 N5 -177.9(9) 6_556 . . . ?
C22 C5 C22 C18 2(2) 6_556 . . . ?
C22 N5 C21 N4 172.3(9) . . . . ?
C22 N5 N6 C1 -173.0(8) . . . . ?
C22 C18 C23 O11 23(2) . . . . ?
C22 C18 C23 O20 -157.3(11) . . . . ?
C23 C18 C22 C5 -172.6(13) . . . . ?
C23 C18 C22 N5 7.4(18) . . . . ?
C1 N4 C21 N5 -1.6(11) . . . . ?
N6 N5 C21 N4 1.8(11) . . . . ?
N6 N5 C22 C5 40.4(14) . . . . ?
N6 N5 C22 C18 -139.5(10) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.592 -0.815 0.250 731.5 226.1 ?
2 -0.441 -0.396 0.750 731.5 226.1 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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 
# 
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data_210411d_sq
_database_code_depnum_ccdc_archive 'CCDC 2202297'
loop_
_audit_author_name
_audit_author_address
'Xiaoxue Ma'
;Liaocheng University
China
;
_audit_update_record             
;
2022-08-19 deposited with the CCDC.	2024-04-12 downloaded from the CCDC.
;
_audit_creation_date             2021-06-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 N6 O5 Zn'
_chemical_formula_sum            'C12 H8 N6 O5 Zn'
_chemical_formula_weight         381.61
_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                   10.2034(8)
_cell_length_b                   16.0013(13)
_cell_length_c                   8.7996(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.181(3)
_cell_angle_gamma                90
_cell_volume                     1422.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2776
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      28.407
_cell_measurement_theta_min      2.385
_shelx_estimated_absorpt_T_max   0.872
_shelx_estimated_absorpt_T_min   0.803
_exptl_absorpt_coefficient_mu    1.767
_exptl_absorpt_correction_T_max  0.868
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6647
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.014
_diffrn_reflns_theta_max         25.014
_diffrn_reflns_theta_min         2.016
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1988
_reflns_number_total             2509
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 V6.36A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V6.36A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2509
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.288
_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)+(0.0417P)²+1.0939P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0982
_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. Restrained distances
 O1_$1-O4_$2
 3.2 with sigma of 0.01
3.a Rotating group:
 O5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C6(H6), C9(H9), C10(H10), C11(H11), C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
N6 N 0.0574(3) 0.1429(2) 0.2863(4) 0.0236(8) Uani 1 1 d . . . . .
C12 C 0.1312(3) 0.0883(3) 0.3693(4) 0.0197(8) Uani 1 1 d . . . . .
H12 H 0.118355 0.030792 0.365181 0.024 Uiso 1 1 calc R U . . .
N4 N 0.2268(3) 0.1269(2) 0.4602(4) 0.0221(7) Uani 1 1 d . . . . .
O5 O 1.0462(3) 0.4040(2) 0.4767(3) 0.0362(8) Uani 1 1 d . . . . .
H5A H 1.097719 0.440786 0.523921 0.054 Uiso 1 1 d R U . . .
H5B H 1.013010 0.428331 0.393572 0.054 Uiso 1 1 d R U . . .
O1 O 0.2235(3) -0.06914(18) 0.7756(3) 0.0290(7) Uani 1 1 d . . . . .
C7 C 0.2103(4) 0.0023(3) 0.7173(4) 0.0227(9) Uani 1 1 d . . . . .
C1 C 0.3360(3) 0.0389(2) 0.6728(4) 0.0184(8) Uani 1 1 d . . . . .
C6 C 0.4553(3) 0.0175(2) 0.7626(4) 0.0192(8) Uani 1 1 d . . . . .
H6 H 0.454999 -0.024321 0.835942 0.023 Uiso 1 1 calc R U . . .
O4 O 0.7641(3) 0.10222(18) 0.9039(3) 0.0305(7) Uani 1 1 d . . . . .
C8 C 0.6967(3) 0.0393(3) 0.8608(4) 0.0209(9) Uani 1 1 d . . . . .
C5 C 0.5741(3) 0.0562(2) 0.7466(4) 0.0185(8) Uani 1 1 d . . . . .
C4 C 0.5729(3) 0.1134(2) 0.6280(4) 0.0179(8) Uani 1 1 d . . . . .
Zn1 Zn 0.90040(4) 0.37695(3) 0.60076(5) 0.01895(16) Uani 1 1 d . . . . .
N2 N 0.8046(3) 0.1163(2) 0.5894(4) 0.0251(8) Uani 1 1 d . . . . .
O3 O 0.7197(3) -0.03406(19) 0.9000(3) 0.0361(8) Uani 1 1 d . . . . .
N3 N 0.6905(3) 0.1574(2) 0.6055(3) 0.0189(7) Uani 1 1 d . . . . .
O2 O 0.1069(3) 0.0441(2) 0.6988(3) 0.0333(7) Uani 1 1 d . . . . .
N1 N 0.8337(3) 0.2551(2) 0.5939(4) 0.0214(7) Uani 1 1 d . . . . .
C9 C 0.8872(4) 0.1783(2) 0.5828(4) 0.0225(9) Uani 1 1 d . . . . .
H9 H 0.975580 0.170267 0.571360 0.027 Uiso 1 1 calc R U . . .
C10 C 0.7100(4) 0.2389(2) 0.6081(5) 0.0253(9) Uani 1 1 d . . . . .
H10 H 0.645757 0.278916 0.618456 0.030 Uiso 1 1 calc R U . . .
C11 C 0.1136(4) 0.2169(3) 0.3296(5) 0.0341(11) Uani 1 1 d . . . . .
H11 H 0.082362 0.267520 0.287058 0.041 Uiso 1 1 calc R U . . .
N5 N 0.2164(3) 0.2111(2) 0.4371(4) 0.0363(9) Uani 1 1 d . . . . .
C3 C 0.4596(4) 0.1322(2) 0.5314(4) 0.0222(9) Uani 1 1 d . . . . .
H3 H 0.462035 0.168360 0.449093 0.027 Uiso 1 1 calc R U . . .
C2 C 0.3412(4) 0.0967(2) 0.5582(4) 0.0200(9) 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
N6 C12 1.307(5) . ?
N6 Zn1 2.142(3) 4_465 ?
N6 C11 1.346(5) . ?
C12 H12 0.9300 . ?
C12 N4 1.322(5) . ?
N4 N5 1.366(5) . ?
N4 C2 1.433(5) . ?
O5 H5A 0.8556 . ?
O5 H5B 0.8550 . ?
O5 Zn1 2.014(3) . ?
O1 C7 1.252(5) . ?
O1 Zn1 1.979(3) 2_646 ?
C7 C1 1.511(5) . ?
C7 O2 1.241(5) . ?
C1 C6 1.396(5) . ?
C1 C2 1.375(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.386(5) . ?
O4 C8 1.248(5) . ?
O4 Zn1 2.088(3) 4_566 ?
C8 C5 1.514(5) . ?
C8 O3 1.236(5) . ?
C5 C4 1.387(5) . ?
C4 N3 1.430(5) . ?
C4 C3 1.367(5) . ?
Zn1 N1 2.063(3) . ?
N2 N3 1.361(4) . ?
N2 C9 1.309(5) . ?
N3 C10 1.319(5) . ?
N1 C9 1.354(5) . ?
N1 C10 1.312(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 N5 1.312(5) . ?
C3 H3 0.9300 . ?
C3 C2 1.386(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
C12 N6 Zn1 129.5(3) . 4_465 ?
C12 N6 C11 103.9(3) . . ?
C11 N6 Zn1 126.0(3) . 4_465 ?
N6 C12 H12 125.0 . . ?
N6 C12 N4 110.1(4) . . ?
N4 C12 H12 125.0 . . ?
C12 N4 N5 109.6(3) . . ?
C12 N4 C2 132.4(3) . . ?
N5 N4 C2 117.5(3) . . ?
H5A O5 H5B 104.1 . . ?
Zn1 O5 H5A 109.6 . . ?
Zn1 O5 H5B 109.2 . . ?
C7 O1 Zn1 125.6(3) . 2_646 ?
O1 C7 C1 114.5(3) . . ?
O2 C7 O1 125.9(4) . . ?
O2 C7 C1 119.6(4) . . ?
C6 C1 C7 117.5(3) . . ?
C2 C1 C7 125.0(3) . . ?
C2 C1 C6 117.3(3) . . ?
C1 C6 H6 118.7 . . ?
C5 C6 C1 122.5(4) . . ?
C5 C6 H6 118.7 . . ?
C8 O4 Zn1 130.9(3) . 4_566 ?
O4 C8 C5 115.2(4) . . ?
O3 C8 O4 127.4(4) . . ?
O3 C8 C5 117.4(3) . . ?
C6 C5 C8 120.4(3) . . ?
C6 C5 C4 117.2(3) . . ?
C4 C5 C8 122.3(3) . . ?
C5 C4 N3 120.8(3) . . ?
C3 C4 C5 122.0(3) . . ?
C3 C4 N3 117.2(3) . . ?
O5 Zn1 N6 85.11(12) . 4_666 ?
O5 Zn1 O4 88.43(11) . 4_565 ?
O5 Zn1 N1 116.98(13) . . ?
O1 Zn1 N6 96.49(12) 2_656 4_666 ?
O1 Zn1 O5 141.55(13) 2_656 . ?
O1 Zn1 O4 89.08(11) 2_656 4_565 ?
O1 Zn1 N1 101.19(12) 2_656 . ?
O4 Zn1 N6 173.48(12) 4_565 4_666 ?
N1 Zn1 N6 95.15(12) . 4_666 ?
N1 Zn1 O4 87.06(12) . 4_565 ?
C9 N2 N3 101.8(3) . . ?
N2 N3 C4 121.5(3) . . ?
C10 N3 C4 127.8(3) . . ?
C10 N3 N2 110.5(3) . . ?
C9 N1 Zn1 136.5(2) . . ?
C10 N1 Zn1 120.1(3) . . ?
C10 N1 C9 103.4(3) . . ?
N2 C9 N1 114.6(3) . . ?
N2 C9 H9 122.7 . . ?
N1 C9 H9 122.7 . . ?
N3 C10 H10 125.1 . . ?
N1 C10 N3 109.8(3) . . ?
N1 C10 H10 125.1 . . ?
N6 C11 H11 123.0 . . ?
N5 C11 N6 114.0(4) . . ?
N5 C11 H11 123.0 . . ?
C11 N5 N4 102.3(3) . . ?
C4 C3 H3 120.5 . . ?
C4 C3 C2 119.0(3) . . ?
C2 C3 H3 120.5 . . ?
C1 C2 N4 123.7(3) . . ?
C1 C2 C3 121.8(3) . . ?
C3 C2 N4 114.5(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
N6 C12 N4 N5 0.1(5) . . . . ?
N6 C12 N4 C2 -171.4(4) . . . . ?
N6 C11 N5 N4 1.4(5) . . . . ?
C12 N6 C11 N5 -1.3(5) . . . . ?
C12 N4 N5 C11 -0.9(5) . . . . ?
C12 N4 C2 C1 -55.7(6) . . . . ?
C12 N4 C2 C3 126.0(4) . . . . ?
O1 C7 C1 C6 -32.5(5) . . . . ?
O1 C7 C1 C2 152.9(4) . . . . ?
C7 C1 C6 C5 -170.6(3) . . . . ?
C7 C1 C2 N4 -3.2(6) . . . . ?
C7 C1 C2 C3 175.0(4) . . . . ?
C1 C6 C5 C8 171.5(4) . . . . ?
C1 C6 C5 C4 -5.1(6) . . . . ?
C6 C1 C2 N4 -177.9(3) . . . . ?
C6 C1 C2 C3 0.4(6) . . . . ?
C6 C5 C4 N3 178.6(3) . . . . ?
C6 C5 C4 C3 0.9(6) . . . . ?
O4 C8 C5 C6 -136.5(4) . . . . ?
O4 C8 C5 C4 40.0(5) . . . . ?
C8 C5 C4 N3 2.0(6) . . . . ?
C8 C5 C4 C3 -175.7(4) . . . . ?
C5 C4 N3 N2 54.6(5) . . . . ?
C5 C4 N3 C10 -120.1(4) . . . . ?
C5 C4 C3 C2 3.7(6) . . . . ?
C4 N3 C10 N1 175.3(3) . . . . ?
C4 C3 C2 N4 174.0(3) . . . . ?
C4 C3 C2 C1 -4.3(6) . . . . ?
Zn1 N6 C12 N4 172.7(2) 4_465 . . . ?
Zn1 N6 C11 N5 -173.7(3) 4_465 . . . ?
Zn1 O1 C7 C1 161.7(2) 2_646 . . . ?
Zn1 O1 C7 O2 -16.1(6) 2_646 . . . ?
Zn1 O4 C8 C5 157.9(3) 4_566 . . . ?
Zn1 O4 C8 O3 -22.6(6) 4_566 . . . ?
Zn1 N1 C9 N2 177.3(3) . . . . ?
Zn1 N1 C10 N3 -177.9(2) . . . . ?
N2 N3 C10 N1 0.2(5) . . . . ?
O3 C8 C5 C6 44.0(5) . . . . ?
O3 C8 C5 C4 -139.6(4) . . . . ?
N3 C4 C3 C2 -174.1(3) . . . . ?
N3 N2 C9 N1 0.2(4) . . . . ?
O2 C7 C1 C6 145.5(4) . . . . ?
O2 C7 C1 C2 -29.2(6) . . . . ?
C9 N2 N3 C4 -175.7(3) . . . . ?
C9 N2 N3 C10 -0.2(4) . . . . ?
C9 N1 C10 N3 -0.1(4) . . . . ?
C10 N1 C9 N2 -0.1(4) . . . . ?
C11 N6 C12 N4 0.7(4) . . . . ?
N5 N4 C2 C1 133.4(4) . . . . ?
N5 N4 C2 C3 -44.9(5) . . . . ?
C3 C4 N3 N2 -127.6(4) . . . . ?
C3 C4 N3 C10 57.7(5) . . . . ?
C2 N4 N5 C11 172.1(4) . . . . ?
C2 C1 C6 C5 4.5(6) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.419 0.250 -0.303 61.1 18.6 ?
2 0.581 0.750 0.921 61.1 18.8 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
