# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_ZnL
_database_code_depnum_ccdc_archive 'CCDC 2004330'
loop_
_audit_author_name
_audit_author_address
Zn-A
;Zhejiang University
China
;
_audit_update_record             
;
2020-05-18 deposited with the CCDC.	2023-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H11 N O4 Zn'
_chemical_formula_weight         382.66

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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.
;

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

_cell_length_a                   8.3095(8)
_cell_length_b                   15.1037(11)
_cell_length_c                   15.3202(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.180(6)
_cell_angle_gamma                90
_cell_volume                     1921.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3622
_cell_measurement_theta_min      2.661
_cell_measurement_theta_max      25.965

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.298
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Bruker P4'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9655
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.894
_diffrn_reflns_theta_max         25.988
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1845
_reflns_number_gt                1485
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0454P)²+0.5555P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1845
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0819
_refine_ls_wR_factor_gt          0.0773
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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_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 0.2500 0.01717(2) -0.5000 0.04436(17) Uani 1 2 d S T P . .
O2 O 0.1497(2) 0.09193(12) -0.41355(11) 0.0537(5) Uani 1 1 d . . . . .
O15 O -0.0423(2) -0.00884(10) -0.39931(11) 0.0506(5) Uani 1 1 d . . . . .
N5 N -0.2500 0.38121(15) 0.0000 0.0347(6) Uani 1 2 d S T P . .
C2 C -0.2500 0.19824(19) 0.0000 0.0346(7) Uani 1 2 d S T P . .
H2 H -0.2500 0.1367 0.0000 0.042 Uiso 1 2 calc R U P . .
C3 C -0.1892(3) 0.33561(13) -0.06616(13) 0.0339(5) Uani 1 1 d . . . . .
H3 H -0.1448 0.3671 -0.1115 0.041 Uiso 1 1 calc R U . . .
C4 C 0.0319(3) 0.05984(15) -0.37552(14) 0.0431(6) Uani 1 1 d . . . . .
C6 C -0.1301(3) 0.19737(14) -0.14827(13) 0.0344(5) Uani 1 1 d . . . . .
C8 C -0.1892(3) 0.24400(13) -0.07050(13) 0.0314(5) Uani 1 1 d . . . . .
C9 C -0.1962(3) 0.11660(15) -0.17404(14) 0.0456(6) Uani 1 1 d . . . . .
H9 H -0.2776 0.0919 -0.1420 0.055 Uiso 1 1 calc R U . . .
C10 C -0.1434(3) 0.07249(15) -0.24615(15) 0.0471(6) Uani 1 1 d . . . . .
H10 H -0.1896 0.0185 -0.2622 0.056 Uiso 1 1 calc R U . . .
C12 C -0.0215(3) 0.10788(14) -0.29521(14) 0.0385(5) Uani 1 1 d . . . . .
C13 C -0.0081(3) 0.23269(15) -0.19779(14) 0.0399(5) Uani 1 1 d . . . . .
H13 H 0.0381 0.2867 -0.1819 0.048 Uiso 1 1 calc R U . . .
C15 C 0.0448(3) 0.18828(16) -0.27009(14) 0.0432(6) Uani 1 1 d . . . . .
H15 H 0.1262 0.2128 -0.3024 0.052 Uiso 1 1 calc R U . . .


_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 O2 1.9514(16) 2_554 ?
Zn1 O2 1.9514(16) . ?
Zn1 N5 2.053(2) 3_544 ?
Zn1 O15 2.2744(19) 5_554 ?
Zn1 O15 2.2744(19) 6_655 ?
O2 C4 1.255(3) . ?
O15 C4 1.253(3) . ?
O15 Zn1 2.2744(19) 5_554 ?
N5 C3 1.340(2) . ?
N5 C3 1.340(2) 2_455 ?
N5 Zn1 2.053(2) 3_455 ?
C2 C8 1.393(2) 2_455 ?
C2 C8 1.393(2) . ?
C2 H2 0.9300 . ?
C3 C8 1.385(3) . ?
C3 H3 0.9300 . ?
C4 C12 1.509(3) . ?
C6 C9 1.389(3) . ?
C6 C13 1.395(3) . ?
C6 C8 1.484(3) . ?
C9 C10 1.376(3) . ?
C9 H9 0.9300 . ?
C10 C12 1.391(3) . ?
C10 H10 0.9300 . ?
C12 C15 1.382(3) . ?
C13 C15 1.381(3) . ?
C13 H13 0.9300 . ?
C15 H15 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
O2 Zn1 O2 109.29(11) 2_554 . ?
O2 Zn1 N5 125.35(5) 2_554 3_544 ?
O2 Zn1 N5 125.35(5) . 3_544 ?
O2 Zn1 O15 84.52(7) 2_554 5_554 ?
O2 Zn1 O15 99.18(7) . 5_554 ?
N5 Zn1 O15 86.83(4) 3_544 5_554 ?
O2 Zn1 O15 99.18(7) 2_554 6_655 ?
O2 Zn1 O15 84.52(7) . 6_655 ?
N5 Zn1 O15 86.83(4) 3_544 6_655 ?
O15 Zn1 O15 173.65(8) 5_554 6_655 ?
C4 O2 Zn1 116.90(15) . . ?
C4 O15 Zn1 126.50(15) . 5_554 ?
C3 N5 C3 118.1(2) . 2_455 ?
C3 N5 Zn1 120.93(12) . 3_455 ?
C3 N5 Zn1 120.93(12) 2_455 3_455 ?
C8 C2 C8 120.5(3) 2_455 . ?
C8 C2 H2 119.7 2_455 . ?
C8 C2 H2 119.7 . . ?
N5 C3 C8 123.40(19) . . ?
N5 C3 H3 118.3 . . ?
C8 C3 H3 118.3 . . ?
O15 C4 O2 124.6(2) . . ?
O15 C4 C12 118.6(2) . . ?
O2 C4 C12 116.8(2) . . ?
C9 C6 C13 117.97(19) . . ?
C9 C6 C8 120.37(19) . . ?
C13 C6 C8 121.66(19) . . ?
C3 C8 C2 117.23(19) . . ?
C3 C8 C6 120.89(18) . . ?
C2 C8 C6 121.87(19) . . ?
C10 C9 C6 121.2(2) . . ?
C10 C9 H9 119.4 . . ?
C6 C9 H9 119.4 . . ?
C9 C10 C12 120.6(2) . . ?
C9 C10 H10 119.7 . . ?
C12 C10 H10 119.7 . . ?
C15 C12 C10 118.6(2) . . ?
C15 C12 C4 121.5(2) . . ?
C10 C12 C4 119.9(2) . . ?
C15 C13 C6 120.7(2) . . ?
C15 C13 H13 119.7 . . ?
C6 C13 H13 119.7 . . ?
C13 C15 C12 121.0(2) . . ?
C13 C15 H15 119.5 . . ?
C12 C15 H15 119.5 . . ?

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
C3 N5 C3 C8 1.45(16) 2_455 . . . ?
Zn1 N5 C3 C8 -178.55(16) 3_455 . . . ?
Zn1 O15 C4 O2 -86.0(3) 5_554 . . . ?
Zn1 O15 C4 C12 94.5(2) 5_554 . . . ?
Zn1 O2 C4 O15 -13.0(3) . . . . ?
Zn1 O2 C4 C12 166.40(15) . . . . ?
N5 C3 C8 C2 -2.8(3) . . . . ?
N5 C3 C8 C6 175.89(18) . . . . ?
C8 C2 C8 C3 1.29(14) 2_455 . . . ?
C8 C2 C8 C6 -177.4(2) 2_455 . . . ?
C9 C6 C8 C3 -148.4(2) . . . . ?
C13 C6 C8 C3 31.3(3) . . . . ?
C9 C6 C8 C2 30.2(3) . . . . ?
C13 C6 C8 C2 -150.1(2) . . . . ?
C13 C6 C9 C10 0.0(4) . . . . ?
C8 C6 C9 C10 179.7(2) . . . . ?
C6 C9 C10 C12 0.1(4) . . . . ?
C9 C10 C12 C15 -0.2(4) . . . . ?
C9 C10 C12 C4 -178.3(2) . . . . ?
O15 C4 C12 C15 -173.8(2) . . . . ?
O2 C4 C12 C15 6.7(3) . . . . ?
O15 C4 C12 C10 4.2(3) . . . . ?
O2 C4 C12 C10 -175.2(2) . . . . ?
C9 C6 C13 C15 -0.1(3) . . . . ?
C8 C6 C13 C15 -179.8(2) . . . . ?
C6 C13 C15 C12 0.0(4) . . . . ?
C10 C12 C15 C13 0.2(4) . . . . ?
C4 C12 C15 C13 178.3(2) . . . . ?

_refine_diff_density_max         0.307
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-2



