# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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. 
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data_mo_2024010812_0m
_database_code_depnum_ccdc_archive 'CCDC 2324324'
loop_
_audit_author_name
_audit_author_address
'Jinjian liu'
;Shanxi Normal University
China
;
_audit_update_record             
;
2024-01-09 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
_audit_creation_date             2024-01-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 N O6 Zn'
_chemical_formula_sum            'C21 H14 N O6 Zn'
_chemical_formula_weight         441.70
_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                   20.1367(18)
_cell_length_b                   11.0593(11)
_cell_length_c                   21.1107(18)
_cell_angle_alpha                90
_cell_angle_beta                 127.242(2)
_cell_angle_gamma                90
_cell_volume                     3742.6(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7260
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.375
_cell_measurement_theta_min      2.237
_shelx_estimated_absorpt_T_max   0.774
_shelx_estimated_absorpt_T_min   0.774
_exptl_absorpt_coefficient_mu    1.352
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            26521
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.499
_diffrn_reflns_theta_min         2.147
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2902
_reflns_number_total             4736
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.839
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4736
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1225
_refine_ls_R_factor_gt           0.0577
_refine_ls_restrained_S_all      1.080
_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)+(0.0495P)²+5.2375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1320
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C22(H22), C6(H6), C2(H2), C3(H3), C17(H17), C18(H18), C9(H9),
 C4(H4), C12(H12), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.88305(2) 0.59832(4) 0.69344(2) 0.03962(15) Uani 1 1 d . . . . .
O5 O 0.56879(16) 0.7998(2) 0.34723(15) 0.0517(7) Uani 1 1 d . . . . .
O6 O 0.43622(16) 0.8279(3) 0.29828(15) 0.0561(7) Uani 1 1 d . . . . .
O3 O 0.76928(15) 0.6579(3) 0.61831(15) 0.0547(7) Uani 1 1 d . . . . .
N1 N 0.7156(2) -0.0302(3) 0.64198(19) 0.0473(8) Uani 1 1 d . . . . .
O1 O 0.8687(2) 0.4182(2) 0.7172(2) 0.0704(9) Uani 1 1 d . . . . .
C21 C 0.5092(2) 0.7910(3) 0.34999(19) 0.0384(8) Uani 1 1 d . . . . .
C20 C 0.5258(2) 0.7334(3) 0.42213(19) 0.0346(7) Uani 1 1 d . . . . .
O2 O 0.9112(2) 0.4398(3) 0.6473(2) 0.0848(11) Uani 1 1 d . . . . .
O4 O 0.7289(2) 0.6153(4) 0.69223(19) 0.0949(13) Uani 1 1 d . . . . .
C19 C 0.4616(2) 0.7100(3) 0.4269(2) 0.0447(9) Uani 1 1 d . . . . .
H19 H 0.4067 0.7247 0.3833 0.054 Uiso 1 1 calc R U . . .
C22 C 0.6074(2) 0.7090(3) 0.48733(19) 0.0369(8) Uani 1 1 d . . . . .
H22 H 0.6506 0.7224 0.4837 0.044 Uiso 1 1 calc R U . . .
C1 C 0.5455(2) -0.0074(3) 0.5297(2) 0.0431(9) Uani 1 1 d . . . . .
C16 C 0.6254(2) 0.6651(3) 0.5574(2) 0.0390(8) Uani 1 1 d . . . . .
C6 C 0.6656(3) -0.0480(4) 0.6624(2) 0.0511(10) Uani 1 1 d . . . . .
H6 H 0.6886 -0.0674 0.7148 0.061 Uiso 1 1 calc R U . . .
C15 C 0.7142(2) 0.6427(4) 0.6288(2) 0.0503(10) Uani 1 1 d . . . . .
C2 C 0.5813(3) -0.0382(3) 0.6079(2) 0.0487(10) Uani 1 1 d . . . . .
H2 H 0.5474 -0.0524 0.6233 0.058 Uiso 1 1 calc R U . . .
C3 C 0.5988(3) 0.0088(4) 0.5101(2) 0.0530(10) Uani 1 1 d . . . . .
H3 H 0.5775 0.0291 0.4582 0.064 Uiso 1 1 calc R U . . .
C17 C 0.5598(2) 0.6437(4) 0.5610(2) 0.0508(10) Uani 1 1 d . . . . .
H17 H 0.5709 0.6148 0.6079 0.061 Uiso 1 1 calc R U . . .
C18 C 0.4790(2) 0.6647(4) 0.4964(2) 0.0530(10) Uani 1 1 d . . . . .
H18 H 0.4357 0.6483 0.4994 0.064 Uiso 1 1 calc R U . . .
C9 C 0.8537(2) 0.1645(3) 0.6939(2) 0.0491(10) Uani 1 1 d . . . . .
H9 H 0.8285 0.1976 0.7150 0.059 Uiso 1 1 calc R U . . .
C4 C 0.6829(3) -0.0049(4) 0.5665(3) 0.0572(11) Uani 1 1 d . . . . .
H4 H 0.7180 0.0036 0.5519 0.069 Uiso 1 1 calc R U . . .
C8 C 0.8539(3) 0.0403(4) 0.6857(2) 0.0506(10) Uani 1 1 d . . . . .
C7 C 0.8083(3) -0.0406(4) 0.7044(3) 0.0582(11) Uani 1 1 d . . . . .
H7A H 0.8226 -0.0187 0.7558 0.070 Uiso 1 1 calc R U . . .
H7B H 0.8254 -0.1237 0.7074 0.070 Uiso 1 1 calc R U . . .
C14 C 0.8899(3) 0.3748(4) 0.6792(3) 0.0548(11) Uani 1 1 d . . . . .
C13 C 0.8905(2) 0.2395(3) 0.6713(2) 0.0490(9) Uani 1 1 d . . . . .
C12 C 0.9290(3) 0.1889(4) 0.6409(3) 0.0654(12) Uani 1 1 d . . . . .
H12 H 0.9535 0.2387 0.6248 0.078 Uiso 1 1 calc R U . . .
C10 C 0.8929(3) -0.0080(4) 0.6558(3) 0.0654(12) Uani 1 1 d . . . . .
H10 H 0.8933 -0.0913 0.6500 0.079 Uiso 1 1 calc R U . . .
C11 C 0.9312(3) 0.0660(4) 0.6347(3) 0.0743(14) Uani 1 1 d . . . . .
H11 H 0.9588 0.0325 0.6161 0.089 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 O5 1.989(2) 7_666 ?
Zn1 O6 1.961(3) 8_566 ?
Zn1 O3 1.950(3) . ?
Zn1 O1 2.116(3) . ?
Zn1 O2 2.238(3) . ?
Zn1 C14 2.504(4) . ?
O5 Zn1 1.989(2) 7_666 ?
O5 C21 1.240(4) . ?
O6 Zn1 1.960(3) 8_465 ?
O6 C21 1.255(4) . ?
O3 C15 1.267(4) . ?
N1 C6 1.326(5) . ?
N1 C4 1.335(5) . ?
N1 C7 1.502(5) . ?
O1 C14 1.213(5) . ?
C21 C20 1.491(5) . ?
C20 C19 1.379(5) . ?
C20 C22 1.390(5) . ?
O2 C14 1.226(5) . ?
O4 C15 1.222(5) . ?
C19 H19 0.9300 . ?
C19 C18 1.381(5) . ?
C22 H22 0.9300 . ?
C22 C16 1.382(5) . ?
C1 C1 1.475(8) 5_656 ?
C1 C2 1.385(5) . ?
C1 C3 1.376(5) . ?
C16 C15 1.506(5) . ?
C16 C17 1.386(5) . ?
C6 H6 0.9300 . ?
C6 C2 1.362(5) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.367(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.370(5) . ?
C18 H18 0.9300 . ?
C9 H9 0.9300 . ?
C9 C8 1.385(5) . ?
C9 C13 1.375(5) . ?
C4 H4 0.9300 . ?
C8 C7 1.498(5) . ?
C8 C10 1.378(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C14 C13 1.507(5) . ?
C13 C12 1.389(5) . ?
C12 H12 0.9300 . ?
C12 C11 1.369(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.371(6) . ?
C11 H11 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
O5 Zn1 O1 143.92(12) 7_666 . ?
O5 Zn1 O2 86.47(12) 7_666 . ?
O5 Zn1 C14 115.55(13) 7_666 . ?
O6 Zn1 O5 100.11(11) 8_566 7_666 ?
O6 Zn1 O1 100.60(12) 8_566 . ?
O6 Zn1 O2 135.09(14) 8_566 . ?
O6 Zn1 C14 120.97(13) 8_566 . ?
O3 Zn1 O5 95.57(11) . 7_666 ?
O3 Zn1 O6 110.34(12) . 8_566 ?
O3 Zn1 O1 104.41(13) . . ?
O3 Zn1 O2 113.15(14) . . ?
O3 Zn1 C14 111.04(13) . . ?
O1 Zn1 O2 58.18(11) . . ?
O1 Zn1 C14 28.91(13) . . ?
O2 Zn1 C14 29.28(12) . . ?
C21 O5 Zn1 143.4(2) . 7_666 ?
C21 O6 Zn1 132.0(2) . 8_465 ?
C15 O3 Zn1 122.4(2) . . ?
C6 N1 C4 119.7(4) . . ?
C6 N1 C7 119.2(3) . . ?
C4 N1 C7 121.1(3) . . ?
C14 O1 Zn1 93.6(3) . . ?
O5 C21 O6 126.2(3) . . ?
O5 C21 C20 117.2(3) . . ?
O6 C21 C20 116.6(3) . . ?
C19 C20 C21 120.9(3) . . ?
C19 C20 C22 119.4(3) . . ?
C22 C20 C21 119.6(3) . . ?
C14 O2 Zn1 87.5(3) . . ?
C20 C19 H19 120.0 . . ?
C20 C19 C18 119.9(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C22 H22 119.5 . . ?
C16 C22 C20 121.0(3) . . ?
C16 C22 H22 119.5 . . ?
C2 C1 C1 121.5(4) . 5_656 ?
C3 C1 C1 121.6(4) . 5_656 ?
C3 C1 C2 116.9(4) . . ?
C22 C16 C15 120.7(3) . . ?
C22 C16 C17 118.5(3) . . ?
C17 C16 C15 120.7(3) . . ?
N1 C6 H6 119.4 . . ?
N1 C6 C2 121.1(4) . . ?
C2 C6 H6 119.4 . . ?
O3 C15 C16 116.0(3) . . ?
O4 C15 O3 124.5(4) . . ?
O4 C15 C16 119.4(4) . . ?
C1 C2 H2 119.7 . . ?
C6 C2 C1 120.6(3) . . ?
C6 C2 H2 119.7 . . ?
C1 C3 H3 119.9 . . ?
C4 C3 C1 120.3(4) . . ?
C4 C3 H3 119.9 . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.0(4) . . ?
C18 C17 H17 119.5 . . ?
C19 C18 H18 119.9 . . ?
C17 C18 C19 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C8 C9 H9 119.6 . . ?
C13 C9 H9 119.6 . . ?
C13 C9 C8 120.7(4) . . ?
N1 C4 C3 121.3(4) . . ?
N1 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C9 C8 C7 120.7(4) . . ?
C10 C8 C9 119.2(4) . . ?
C10 C8 C7 120.0(4) . . ?
N1 C7 H7A 109.4 . . ?
N1 C7 H7B 109.4 . . ?
C8 C7 N1 111.0(3) . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
O1 C14 Zn1 57.5(2) . . ?
O1 C14 O2 120.7(4) . . ?
O1 C14 C13 119.7(4) . . ?
O2 C14 Zn1 63.3(2) . . ?
O2 C14 C13 119.5(4) . . ?
C13 C14 Zn1 176.9(3) . . ?
C9 C13 C14 121.2(4) . . ?
C9 C13 C12 119.1(4) . . ?
C12 C13 C14 119.7(4) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 C13 120.2(4) . . ?
C11 C12 H12 119.9 . . ?
C8 C10 H10 119.8 . . ?
C11 C10 C8 120.3(4) . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.3(4) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?

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
Zn1 O5 C21 O6 30.6(6) 7_666 . . . ?
Zn1 O5 C21 C20 -148.2(3) 7_666 . . . ?
Zn1 O6 C21 O5 4.2(6) 8_465 . . . ?
Zn1 O6 C21 C20 -177.0(2) 8_465 . . . ?
Zn1 O3 C15 O4 17.0(6) . . . . ?
Zn1 O3 C15 C16 -165.2(2) . . . . ?
Zn1 O1 C14 O2 1.9(5) . . . . ?
Zn1 O1 C14 C13 -178.5(3) . . . . ?
Zn1 O2 C14 O1 -1.8(4) . . . . ?
Zn1 O2 C14 C13 178.6(4) . . . . ?
O5 C21 C20 C19 -174.0(3) . . . . ?
O5 C21 C20 C22 9.7(5) . . . . ?
O6 C21 C20 C19 7.1(5) . . . . ?
O6 C21 C20 C22 -169.3(3) . . . . ?
N1 C6 C2 C1 -1.1(6) . . . . ?
O1 C14 C13 C9 11.7(6) . . . . ?
O1 C14 C13 C12 -168.1(4) . . . . ?
C21 C20 C19 C18 -175.3(3) . . . . ?
C21 C20 C22 C16 174.5(3) . . . . ?
C20 C19 C18 C17 0.5(6) . . . . ?
C20 C22 C16 C15 -177.9(3) . . . . ?
C20 C22 C16 C17 1.1(5) . . . . ?
O2 C14 C13 C9 -168.6(4) . . . . ?
O2 C14 C13 C12 11.6(6) . . . . ?
C19 C20 C22 C16 -1.9(5) . . . . ?
C22 C20 C19 C18 1.1(5) . . . . ?
C22 C16 C15 O3 -5.1(5) . . . . ?
C22 C16 C15 O4 172.9(4) . . . . ?
C22 C16 C17 C18 0.5(6) . . . . ?
C1 C1 C2 C6 -178.1(4) 5_656 . . . ?
C1 C1 C3 C4 179.7(4) 5_656 . . . ?
C1 C3 C4 N1 -2.2(6) . . . . ?
C16 C17 C18 C19 -1.3(6) . . . . ?
C6 N1 C4 C3 3.1(6) . . . . ?
C6 N1 C7 C8 -150.2(4) . . . . ?
C15 C16 C17 C18 179.5(4) . . . . ?
C2 C1 C3 C4 -0.4(6) . . . . ?
C3 C1 C2 C6 2.0(6) . . . . ?
C17 C16 C15 O3 175.9(4) . . . . ?
C17 C16 C15 O4 -6.1(6) . . . . ?
C9 C8 C7 N1 72.3(5) . . . . ?
C9 C8 C10 C11 0.1(7) . . . . ?
C9 C13 C12 C11 -0.9(7) . . . . ?
C4 N1 C6 C2 -1.5(6) . . . . ?
C4 N1 C7 C8 30.6(5) . . . . ?
C8 C9 C13 C14 179.3(4) . . . . ?
C8 C9 C13 C12 -0.9(6) . . . . ?
C8 C10 C11 C12 -1.9(8) . . . . ?
C7 N1 C6 C2 179.3(4) . . . . ?
C7 N1 C4 C3 -177.7(4) . . . . ?
C7 C8 C10 C11 176.7(4) . . . . ?
C14 C13 C12 C11 178.9(4) . . . . ?
C13 C9 C8 C7 -175.3(4) . . . . ?
C13 C9 C8 C10 1.3(6) . . . . ?
C13 C12 C11 C10 2.2(8) . . . . ?
C10 C8 C7 N1 -104.2(5) . . . . ?

_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 
# 
# 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_exp_437_auto
_database_code_depnum_ccdc_archive 'CCDC 2369674'
loop_
_audit_author_name
_audit_author_address
'Jinjian liu'
;Shanxi Normal University
China
;
_audit_update_record             
;
2024-08-08 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
_audit_creation_date             2024-08-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H13 N O7 Zn'
_chemical_formula_sum            'C18 H13 N O7 Zn'
_chemical_formula_weight         420.66
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.9146(4)
_cell_length_b                   10.0980(3)
_cell_length_c                   15.0368(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.246(3)
_cell_angle_gamma                90
_cell_volume                     1635.76(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6211
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0350
_cell_measurement_theta_min      4.0290
_shelx_estimated_absorpt_T_max   0.747
_shelx_estimated_absorpt_T_min   0.654
_exptl_absorpt_coefficient_mu    1.546
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            34381
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.965
_diffrn_reflns_theta_min         3.219
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0710
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00 -22.00   1.00    5.00    --  -18.75 126.00  96.00   51
  2  ω     10.00  37.00   1.00    5.00    --   20.16-145.00-147.00   27
  3  ω     49.00  74.00   1.00    5.00    --   20.16-126.00  19.00   25
  4  ω     -2.00  32.00   1.00    5.00    --   20.16-126.00  19.00   34
  5  ω    -32.00  -6.00   1.00    5.00    --  -18.75 -38.00  60.00   26
  6  ω    -88.00 -60.00   1.00    5.00    --  -18.75 -38.00  60.00   28
  7  ω    -82.00 -57.00   1.00    5.00    --  -18.75 145.00 -96.00   25
  8  ω    -19.00  11.00   1.00    5.00    --  -18.75 -99.00-150.00   30
  9  ω      6.00  87.00   1.00    5.00    --   20.16  57.00 150.00   81
 10  ω      0.00  74.00   1.00    5.00    --   20.16-125.00  87.03   74
 11  ω    -25.00  58.00   1.00    5.00    --   20.16 -99.00 -60.00   83
 12  ω    -25.00  59.00   1.00    5.00    --   20.16 -99.00-150.00   84
 13  ω      1.00  89.00   1.00    5.00    --   20.16  38.00-120.00   88
 14  ω     28.00  89.00   1.00    5.00    --   20.16  38.00 -60.00   61
 15  ω     17.00  87.00   1.00    5.00    --   20.16  57.00  60.00   70
 16  ω     -2.00  88.00   1.00    5.00    --   20.16  77.00 -30.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0029669000
_diffrn_orient_matrix_UB_12      -0.0591621000
_diffrn_orient_matrix_UB_13      0.0256600000
_diffrn_orient_matrix_UB_21      0.0057064000
_diffrn_orient_matrix_UB_22      0.0378486000
_diffrn_orient_matrix_UB_23      0.0401962000
_diffrn_orient_matrix_UB_31      -0.0655409000
_diffrn_orient_matrix_UB_32      0.0006253000
_diffrn_orient_matrix_UB_33      -0.0030582000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3118
_reflns_number_total             4871
_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       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.806
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4871
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.056
_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)+(0.0400P)²+1.9713P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1195
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O7-C17 = C17-O21
 1.25 with sigma of 0.02
 O6-C17 = C17-O20
 1.25 with sigma of 0.02
 O4-C14 = C14-O5
 1.25 with sigma of 0.02
 O8-C14 = C14-O9
 1.25 with sigma of 0.02
 O7-O21
 2.165 with sigma of 0.04
 O6-O20
 2.165 with sigma of 0.04
 O4-O5
 2.165 with sigma of 0.04
 O8-O9
 2.165 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C8 \\sim N1 \\sim C9 \\sim C11 \\sim C13 \\sim C12 \\sim C10 \\sim C7: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 O4, C14, O5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O8, C14, O9
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O20, C17, O6
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O21, C17, O7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(O7)=Sof(O21)=Sof(O8)=Sof(O9)=1-FVAR(1)
 Sof(O6)=Sof(O4)=Sof(O5)=Sof(O20)=FVAR(1)
6.a Rotating group:
 O3(H3A,H3B)
6.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
6.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C11(H11), C12(H12), C10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.72344(3) 0.43496(3) 0.65896(2) 0.04850(14) Uani 1 1 d . . . . .
O3 O 0.5689(2) 0.5464(2) 0.66705(16) 0.0593(6) Uani 1 1 d . . . . .
H3A H 0.512367 0.536808 0.618744 0.089 Uiso 1 1 d R U . . .
H3B H 0.586111 0.631356 0.666235 0.089 Uiso 1 1 d R U . . .
O6 O 0.8934(4) 0.7818(3) 0.8522(3) 0.0377(9) Uani 0.647(8) 1 d D . P A 1
O2 O 0.8036(2) 0.5238(3) 0.56662(16) 0.0650(7) Uani 1 1 d . . . . .
C16 C 0.9283(2) 0.5886(2) 0.94159(15) 0.0260(5) Uani 1 1 d . . . . .
O1 O 0.6368(2) 0.4721(3) 0.46846(18) 0.0805(9) Uani 1 1 d . . . . .
O4 O 0.8437(5) 0.4879(3) 0.7634(2) 0.0431(11) Uani 0.647(8) 1 d D . P A 1
C17 C 0.8506(2) 0.6905(3) 0.88592(16) 0.0342(5) Uani 1 1 d D . . . .
C18 C 0.9917(2) 0.6309(2) 1.02487(16) 0.0318(5) Uani 1 1 d . . . . .
H18 H 0.986474 0.719185 1.041380 0.038 Uiso 1 1 calc R U . . .
C15 C 0.9375(2) 0.4564(2) 0.91634(15) 0.0286(5) Uani 1 1 d . . . . .
C14 C 0.8717(3) 0.4059(3) 0.82632(17) 0.0373(6) Uani 1 1 d D . . . .
C2 C 0.7797(3) 0.6266(3) 0.4238(2) 0.0494(7) Uani 1 1 d . . . . .
N1 N 0.5872(3) 0.7480(4) 0.1591(2) 0.0776(10) Uani 1 1 d . U . . .
C3 C 0.6929(3) 0.6928(3) 0.3626(2) 0.0512(8) Uani 1 1 d . . . . .
H3 H 0.608863 0.677878 0.362691 0.061 Uiso 1 1 calc R U . . .
O7 O 0.7758(8) 0.7592(9) 0.9063(4) 0.049(2) Uani 0.353(8) 1 d D . P A 2
C1 C 0.7350(3) 0.5340(4) 0.4898(2) 0.0558(8) Uani 1 1 d . . . . .
O5 O 0.8383(7) 0.2872(4) 0.8194(4) 0.080(2) Uani 0.647(8) 1 d D . P A 1
C7 C 0.7293(3) 0.7819(4) 0.3007(3) 0.0615(9) Uani 1 1 d . U . . .
C4 C 0.9055(3) 0.6482(4) 0.4212(3) 0.0656(10) Uani 1 1 d . . . . .
H4 H 0.965467 0.604950 0.461947 0.079 Uiso 1 1 calc R U . . .
C5 C 0.9411(3) 0.7337(5) 0.3582(3) 0.0749(12) Uani 1 1 d . . . . .
H5 H 1.025007 0.745765 0.355711 0.090 Uiso 1 1 calc R U . . .
C6 C 0.8537(4) 0.8010(4) 0.2992(3) 0.0751(11) Uani 1 1 d . . . . .
H6 H 0.878797 0.859858 0.258042 0.090 Uiso 1 1 calc R U . . .
C13 C 0.5183(4) 0.5512(5) 0.0335(2) 0.0841(14) Uani 1 1 d . U . . .
C9 C 0.4743(4) 0.6968(6) 0.1497(3) 0.0927(15) Uani 1 1 d . U . . .
H9 H 0.418454 0.727593 0.185614 0.111 Uiso 1 1 calc R U . . .
C8 C 0.6323(4) 0.8453(4) 0.2313(3) 0.0824(12) Uani 1 1 d . U . . .
H8A H 0.563362 0.875278 0.259545 0.099 Uiso 1 1 calc R U . . .
H8B H 0.667369 0.921628 0.205334 0.099 Uiso 1 1 calc R U . . .
C11 C 0.4385(4) 0.5993(7) 0.0879(3) 0.1002(16) Uani 1 1 d . U . . .
H11 H 0.358666 0.564843 0.082474 0.120 Uiso 1 1 calc R U . . .
C12 C 0.6350(5) 0.6074(7) 0.0464(4) 0.1117(17) Uani 1 1 d . U . . .
H12 H 0.693278 0.577911 0.012065 0.134 Uiso 1 1 calc R U . . .
C10 C 0.6662(5) 0.7036(7) 0.1073(4) 0.1132(18) Uani 1 1 d . U . . .
H10 H 0.745257 0.740320 0.113497 0.136 Uiso 1 1 calc R U . . .
O21 O 0.9111(7) 0.7302(11) 0.8174(6) 0.057(2) Uani 0.353(8) 1 d D . P A 2
O8 O 0.7809(9) 0.4720(8) 0.7920(6) 0.052(2) Uani 0.353(8) 1 d D . P A 2
O20 O 0.7322(3) 0.6776(6) 0.8890(3) 0.0616(14) Uani 0.647(8) 1 d D . P A 1
O9 O 0.9189(10) 0.3116(8) 0.7944(4) 0.058(3) Uani 0.353(8) 1 d D . P A 2


_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 2.048(2) . ?
Zn1 O6 1.994(4) 2_646 ?
Zn1 O2 1.972(3) . ?
Zn1 O4 1.953(3) . ?
Zn1 O7 2.029(8) 2_646 ?
Zn1 O8 2.032(7) . ?
O6 C17 1.185(4) . ?
O2 C1 1.276(4) . ?
C16 C17 1.500(3) . ?
C16 C18 1.397(3) . ?
C16 C15 1.396(3) . ?
O1 C1 1.238(4) . ?
O4 C14 1.258(4) . ?
C17 O7 1.149(6) . ?
C17 O21 1.371(7) . ?
C17 O20 1.306(4) . ?
C18 C15 1.391(3) 3_767 ?
C15 C14 1.515(3) . ?
C14 O5 1.252(4) . ?
C14 O8 1.236(6) . ?
C14 O9 1.218(6) . ?
C2 C3 1.382(4) . ?
C2 C1 1.501(5) . ?
C2 C4 1.397(5) . ?
N1 C9 1.323(5) . ?
N1 C8 1.488(6) . ?
N1 C10 1.328(6) . ?
C3 C7 1.397(5) . ?
C7 C6 1.376(5) . ?
C7 C8 1.505(5) . ?
C4 C5 1.384(6) . ?
C5 C6 1.374(6) . ?
C13 C13 1.454(10) 3_665 ?
C13 C11 1.375(7) . ?
C13 C12 1.379(6) . ?
C9 C11 1.367(7) . ?
C12 C10 1.342(8) . ?

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
O6 Zn1 O3 84.80(12) 2_646 . ?
O6 Zn1 O7 48.2(2) 2_646 2_646 ?
O2 Zn1 O3 104.77(10) . . ?
O2 Zn1 O6 130.08(15) . 2_646 ?
O2 Zn1 O7 91.18(19) . 2_646 ?
O2 Zn1 O8 120.5(4) . . ?
O4 Zn1 O3 104.81(17) . . ?
O4 Zn1 O6 128.18(19) . 2_646 ?
O4 Zn1 O2 97.15(16) . . ?
O4 Zn1 O7 125.0(3) . 2_646 ?
O7 Zn1 O3 125.2(3) 2_646 . ?
O7 Zn1 O8 127.8(3) 2_646 . ?
O8 Zn1 O3 88.1(2) . . ?
C17 O6 Zn1 110.4(3) . 2_656 ?
C1 O2 Zn1 114.3(2) . . ?
C18 C16 C17 116.4(2) . . ?
C15 C16 C17 124.2(2) . . ?
C15 C16 C18 119.3(2) . . ?
C14 O4 Zn1 118.4(3) . . ?
O6 C17 C16 123.1(3) . . ?
O6 C17 O20 123.6(3) . . ?
O7 C17 C16 128.8(4) . . ?
O7 C17 O21 118.2(5) . . ?
O21 C17 C16 108.8(4) . . ?
O20 C17 C16 112.7(3) . . ?
C15 C18 C16 121.4(2) 3_767 . ?
C16 C15 C14 121.3(2) . . ?
C18 C15 C16 119.3(2) 3_767 . ?
C18 C15 C14 119.3(2) 3_767 . ?
O4 C14 C15 118.3(3) . . ?
O5 C14 O4 122.4(3) . . ?
O5 C14 C15 119.1(3) . . ?
O8 C14 C15 115.1(4) . . ?
O9 C14 C15 116.4(4) . . ?
O9 C14 O8 128.2(5) . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 C4 118.5(3) . . ?
C4 C2 C1 122.8(3) . . ?
C9 N1 C8 121.9(4) . . ?
C9 N1 C10 119.1(5) . . ?
C10 N1 C8 118.7(4) . . ?
C2 C3 C7 121.1(3) . . ?
C17 O7 Zn1 109.9(6) . 2_656 ?
O2 C1 C2 116.3(3) . . ?
O1 C1 O2 123.5(3) . . ?
O1 C1 C2 120.2(3) . . ?
C3 C7 C8 119.5(3) . . ?
C6 C7 C3 119.2(4) . . ?
C6 C7 C8 121.0(4) . . ?
C5 C4 C2 120.1(4) . . ?
C6 C5 C4 120.6(3) . . ?
C5 C6 C7 120.3(4) . . ?
C11 C13 C13 122.3(5) . 3_665 ?
C11 C13 C12 115.5(5) . . ?
C12 C13 C13 122.3(5) . 3_665 ?
N1 C9 C11 120.9(5) . . ?
N1 C8 C7 109.7(4) . . ?
C9 C11 C13 121.3(4) . . ?
C10 C12 C13 121.4(5) . . ?
N1 C10 C12 121.8(5) . . ?
C14 O8 Zn1 114.3(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.096
_oxdiff_exptl_absorpt_empirical_full_min 0.869
