# 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 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 
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data_111
_audit_block_doi                 10.5517/ccdc.csd.cc2h63vp
_database_code_depnum_ccdc_archive 'CCDC 2299792'
loop_
_audit_author_name
_audit_author_address
ZhuXiaoshuang
;Ningxia University
China
;
_audit_update_record             
;
2023-10-08 deposited with the CCDC.	2024-02-07 downloaded from the CCDC.
;
_audit_creation_date             2018-04-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C7 H5 F3 N O3 Zn0.5)'
_chemical_formula_sum            'C21 H15 F9 N3 O9 Zn1.50'
_chemical_formula_weight         722.41
_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'
F F 0.0171 0.0103 '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                   17.2579(10)
_cell_length_b                   6.5430(4)
_cell_length_c                   22.8388(14)
_cell_angle_alpha                90
_cell_angle_beta                 95.849(2)
_cell_angle_gamma                90
_cell_volume                     2565.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6729
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.998
_cell_measurement_theta_min      3.049
_shelx_estimated_absorpt_T_max   0.849
_shelx_estimated_absorpt_T_min   0.639
_exptl_absorpt_coefficient_mu    1.537
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0774 before and 0.0640 after correction.
The Ratio of minimum to maximum transmission is 0.8059.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.870
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1017
_diffrn_reflns_av_unetI/netI     0.0909
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            33792
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.581
_diffrn_reflns_theta_min         3.048
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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                3568
_reflns_number_total             5938
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.023
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5938
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1409
_refine_ls_R_factor_gt           0.0750
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0650P)²+8.7890P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1528
_refine_ls_wR_factor_ref         0.1750
_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
 H3B-H20
 2.2 with sigma of 0.02
3.a Rotating group:
 O3(H3A,H3B), O6(H6A,H6B), O7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C13(H13), C3(H3), C6(H6), C17(H17), C4(H4), C10(H10), C18(H18),
 C11(H11)
;
_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
Zn1 Zn 0.500000 0.000000 0.500000 0.0260(2) Uani 1 2 d S T P . .
Zn2 Zn 0.33276(4) 0.22489(10) 0.66149(3) 0.0263(2) Uani 1 1 d . . . . .
O5 O 0.3381(2) -0.0538(5) 0.61818(17) 0.0263(9) Uani 1 1 d . . . . .
F3 F 0.1920(2) 0.3236(7) 0.4786(2) 0.0714(14) Uani 1 1 d . . . . .
F2 F 0.1160(2) 0.1062(8) 0.4348(3) 0.0945(18) Uani 1 1 d . . . . .
F1 F 0.1809(3) 0.3085(8) 0.3860(2) 0.0794(15) Uani 1 1 d . . . . .
O2 O 0.5076(2) -0.2786(6) 0.45804(17) 0.0324(9) Uani 1 1 d . . . . .
O3 O 0.4748(2) -0.1551(6) 0.57740(17) 0.0356(10) Uani 1 1 d . . . . .
H3A H 0.445666 -0.079516 0.599162 0.053 Uiso 1 1 d GR . . . .
H3B H 0.517584 -0.175185 0.601920 0.053 Uiso 1 1 d DGR . . . .
F9 F 0.7165(2) 0.0995(7) 0.7308(2) 0.0770(15) Uani 1 1 d . . . . .
O8 O 0.3265(2) 0.4985(6) 0.70457(18) 0.0358(10) Uani 1 1 d . . . . .
O6 O 0.3559(2) 0.3815(6) 0.58369(17) 0.0370(10) Uani 1 1 d . . . . .
H6A H 0.404968 0.382249 0.580668 0.056 Uiso 1 1 d GR . . . .
H6B H 0.344313 0.507993 0.586882 0.056 Uiso 1 1 d GR . . . .
O7 O 0.3085(2) 0.0623(7) 0.73902(19) 0.0422(11) Uani 1 1 d . . . . .
H7A H 0.262064 0.088574 0.746308 0.063 Uiso 1 1 d GR . . . .
H7B H 0.336839 0.109323 0.768644 0.063 Uiso 1 1 d GR . . . .
N3 N 0.4502(2) 0.2510(7) 0.69998(19) 0.0249(10) Uani 1 1 d . . . . .
N1 N 0.3825(2) -0.0373(7) 0.4620(2) 0.0243(10) Uani 1 1 d . . . . .
F8 F 0.6502(2) -0.0998(7) 0.77922(18) 0.0635(12) Uani 1 1 d . . . . .
F7 F 0.6399(2) -0.1159(7) 0.6861(2) 0.0692(13) Uani 1 1 d . . . . .
O4 O 0.2643(3) -0.2853(6) 0.5684(2) 0.0463(12) Uani 1 1 d . . . . .
O9 O 0.4015(2) 0.7354(6) 0.75246(19) 0.0419(11) Uani 1 1 d . . . . .
O1 O 0.4359(3) -0.5111(6) 0.4053(2) 0.0472(12) Uani 1 1 d . . . . .
N2 N 0.2149(2) 0.1951(7) 0.62504(19) 0.0259(10) Uani 1 1 d . . . . .
C20 C 0.5099(3) 0.1197(9) 0.7007(2) 0.0291(13) Uani 1 1 d . . . . .
H20 H 0.502033 -0.006398 0.682254 0.035 Uiso 1 1 calc DR . . . .
C13 C 0.1550(3) 0.3219(9) 0.6273(2) 0.0287(13) Uani 1 1 d . . . . .
H13 H 0.163606 0.450005 0.644399 0.034 Uiso 1 1 calc R . . . .
C5 C 0.3724(3) -0.2166(8) 0.4345(2) 0.0260(12) Uani 1 1 d . . . . .
C7 C 0.4443(3) -0.3488(9) 0.4324(2) 0.0289(13) Uani 1 1 d . . . . .
C19 C 0.4616(3) 0.4301(8) 0.7269(2) 0.0233(12) Uani 1 1 d . . . . .
C14 C 0.2746(3) -0.1219(9) 0.5953(2) 0.0280(13) Uani 1 1 d . . . . .
C21 C 0.3908(3) 0.5689(9) 0.7284(2) 0.0292(13) Uani 1 1 d . . . . .
C3 C 0.2383(3) -0.1473(10) 0.4090(3) 0.0398(16) Uani 1 1 d . . . . .
H3 H 0.189242 -0.185748 0.391813 0.048 Uiso 1 1 calc R . . . .
C16 C 0.5829(3) 0.1668(9) 0.7281(3) 0.0294(13) Uani 1 1 d . . . . .
C12 C 0.2028(3) 0.0117(9) 0.5991(2) 0.0285(13) Uani 1 1 d . . . . .
C2 C 0.2497(3) 0.0402(9) 0.4358(3) 0.0303(13) Uani 1 1 d . . . . .
C6 C 0.3221(3) 0.0913(9) 0.4629(2) 0.0288(13) Uani 1 1 d . . . . .
H6 H 0.329156 0.216464 0.481948 0.035 Uiso 1 1 calc R . . . .
C1 C 0.1853(4) 0.1917(10) 0.4344(3) 0.0414(16) Uani 1 1 d . . . . .
C17 C 0.5947(4) 0.3551(10) 0.7554(3) 0.0405(16) Uani 1 1 d . . . . .
H17 H 0.643396 0.391157 0.773671 0.049 Uiso 1 1 calc R . . . .
C4 C 0.3008(4) -0.2756(9) 0.4082(3) 0.0408(16) Uani 1 1 d . . . . .
H4 H 0.294764 -0.402373 0.389845 0.049 Uiso 1 1 calc R . . . .
C9 C 0.0806(3) 0.2688(10) 0.6050(3) 0.0370(15) Uani 1 1 d . . . . .
C15 C 0.6472(3) 0.0134(10) 0.7308(3) 0.0389(15) Uani 1 1 d . . . . .
C10 C 0.0674(4) 0.0788(12) 0.5794(3) 0.055(2) Uani 1 1 d . . . . .
H10 H 0.017423 0.039613 0.564418 0.066 Uiso 1 1 calc R . . . .
C18 C 0.5331(4) 0.4861(10) 0.7548(3) 0.0432(17) Uani 1 1 d . . . . .
H18 H 0.539255 0.612847 0.773113 0.052 Uiso 1 1 calc R . . . .
C8 C 0.0154(4) 0.4148(13) 0.6073(3) 0.052(2) Uani 1 1 d . . . . .
C11 C 0.1296(4) -0.0513(10) 0.5764(3) 0.0461(17) Uani 1 1 d . . . . .
H11 H 0.122373 -0.179801 0.559320 0.055 Uiso 1 1 calc R . . . .
F4 F -0.0022(4) 0.5132(12) 0.5609(3) 0.157(4) Uani 1 1 d . . . . .
F5 F -0.0457(3) 0.3338(9) 0.6255(3) 0.121(2) Uani 1 1 d . . . . .
F6 F 0.0305(3) 0.5621(9) 0.6479(3) 0.115(2) 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 O2 2.070(4) . ?
Zn1 O2 2.070(4) 3_656 ?
Zn1 O3 2.122(4) 3_656 ?
Zn1 O3 2.122(4) . ?
Zn1 N1 2.138(4) . ?
Zn1 N1 2.138(4) 3_656 ?
Zn2 O5 2.081(4) . ?
Zn2 O8 2.051(4) . ?
Zn2 O6 2.124(4) . ?
Zn2 O7 2.143(4) . ?
Zn2 N3 2.132(4) . ?
Zn2 N2 2.126(4) . ?
O5 C14 1.248(6) . ?
F3 C1 1.324(8) . ?
F2 C1 1.321(7) . ?
F1 C1 1.339(8) . ?
O2 C7 1.271(7) . ?
F9 C15 1.322(7) . ?
O8 C21 1.273(7) . ?
N3 C20 1.340(7) . ?
N3 C19 1.329(7) . ?
N1 C5 1.333(7) . ?
N1 C6 1.341(6) . ?
F8 C15 1.327(7) . ?
F7 C15 1.322(7) . ?
O4 C14 1.237(7) . ?
O9 C21 1.225(7) . ?
O1 C7 1.231(7) . ?
N2 C13 1.331(7) . ?
N2 C12 1.346(7) . ?
C20 C16 1.382(8) . ?
C13 C9 1.377(8) . ?
C5 C7 1.517(8) . ?
C5 C4 1.375(8) . ?
C19 C21 1.525(8) . ?
C19 C18 1.378(8) . ?
C14 C12 1.525(8) . ?
C3 C2 1.376(8) . ?
C3 C4 1.369(8) . ?
C16 C17 1.387(8) . ?
C16 C15 1.493(8) . ?
C12 C11 1.378(8) . ?
C2 C6 1.376(7) . ?
C2 C1 1.487(8) . ?
C17 C18 1.365(8) . ?
C9 C10 1.384(9) . ?
C9 C8 1.481(9) . ?
C10 C11 1.378(9) . ?
C8 F4 1.249(8) . ?
C8 F5 1.286(8) . ?
C8 F6 1.345(9) . ?

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 180.0 . 3_656 ?
O2 Zn1 O3 90.42(16) 3_656 . ?
O2 Zn1 O3 89.58(16) 3_656 3_656 ?
O2 Zn1 O3 89.58(16) . . ?
O2 Zn1 O3 90.42(16) . 3_656 ?
O2 Zn1 N1 100.72(16) 3_656 . ?
O2 Zn1 N1 79.28(16) 3_656 3_656 ?
O2 Zn1 N1 100.72(16) . 3_656 ?
O2 Zn1 N1 79.28(16) . . ?
O3 Zn1 O3 180.0 . 3_656 ?
O3 Zn1 N1 89.04(16) 3_656 . ?
O3 Zn1 N1 90.97(16) . . ?
O3 Zn1 N1 90.96(16) 3_656 3_656 ?
O3 Zn1 N1 89.04(16) . 3_656 ?
N1 Zn1 N1 180.0 . 3_656 ?
O5 Zn2 O6 90.22(15) . . ?
O5 Zn2 O7 88.84(16) . . ?
O5 Zn2 N3 100.35(16) . . ?
O5 Zn2 N2 79.67(16) . . ?
O8 Zn2 O5 179.40(16) . . ?
O8 Zn2 O6 90.22(16) . . ?
O8 Zn2 O7 90.71(17) . . ?
O8 Zn2 N3 80.03(16) . . ?
O8 Zn2 N2 99.93(16) . . ?
O6 Zn2 O7 178.93(17) . . ?
O6 Zn2 N3 93.13(16) . . ?
O6 Zn2 N2 88.29(17) . . ?
N3 Zn2 O7 87.54(17) . . ?
N2 Zn2 O7 91.04(17) . . ?
N2 Zn2 N3 178.58(17) . . ?
C14 O5 Zn2 115.6(3) . . ?
C7 O2 Zn1 116.0(3) . . ?
C21 O8 Zn2 115.8(3) . . ?
C20 N3 Zn2 130.6(4) . . ?
C19 N3 Zn2 110.5(3) . . ?
C19 N3 C20 118.9(5) . . ?
C5 N1 Zn1 111.3(3) . . ?
C5 N1 C6 119.7(5) . . ?
C6 N1 Zn1 129.0(4) . . ?
C13 N2 Zn2 130.1(4) . . ?
C13 N2 C12 119.1(5) . . ?
C12 N2 Zn2 110.7(3) . . ?
N3 C20 C16 121.8(5) . . ?
N2 C13 C9 121.8(6) . . ?
N1 C5 C7 116.7(5) . . ?
N1 C5 C4 121.4(5) . . ?
C4 C5 C7 121.9(5) . . ?
O2 C7 C5 116.6(5) . . ?
O1 C7 O2 126.5(5) . . ?
O1 C7 C5 116.9(5) . . ?
N3 C19 C21 117.0(5) . . ?
N3 C19 C18 122.1(5) . . ?
C18 C19 C21 120.8(5) . . ?
O5 C14 C12 117.2(5) . . ?
O4 C14 O5 126.3(5) . . ?
O4 C14 C12 116.5(5) . . ?
O8 C21 C19 116.1(5) . . ?
O9 C21 O8 126.8(5) . . ?
O9 C21 C19 117.1(5) . . ?
C4 C3 C2 118.3(5) . . ?
C20 C16 C17 119.2(5) . . ?
C20 C16 C15 120.5(5) . . ?
C17 C16 C15 120.2(5) . . ?
N2 C12 C14 116.4(5) . . ?
N2 C12 C11 121.9(5) . . ?
C11 C12 C14 121.7(5) . . ?
C3 C2 C6 120.0(5) . . ?
C3 C2 C1 120.7(5) . . ?
C6 C2 C1 119.3(6) . . ?
N1 C6 C2 120.7(5) . . ?
F3 C1 F1 104.5(6) . . ?
F3 C1 C2 114.3(5) . . ?
F2 C1 F3 106.2(6) . . ?
F2 C1 F1 105.7(6) . . ?
F2 C1 C2 113.1(6) . . ?
F1 C1 C2 112.2(5) . . ?
C18 C17 C16 118.3(6) . . ?
C3 C4 C5 119.8(6) . . ?
C13 C9 C10 119.4(6) . . ?
C13 C9 C8 120.5(6) . . ?
C10 C9 C8 120.1(6) . . ?
F9 C15 F8 106.2(5) . . ?
F9 C15 F7 106.7(5) . . ?
F9 C15 C16 112.5(5) . . ?
F8 C15 C16 112.1(5) . . ?
F7 C15 F8 106.2(6) . . ?
F7 C15 C16 112.7(5) . . ?
C11 C10 C9 118.7(6) . . ?
C17 C18 C19 119.8(6) . . ?
F4 C8 C9 115.0(6) . . ?
F4 C8 F5 110.5(7) . . ?
F4 C8 F6 103.2(8) . . ?
F5 C8 C9 113.3(7) . . ?
F5 C8 F6 100.4(7) . . ?
F6 C8 C9 113.0(6) . . ?
C10 C11 C12 119.1(6) . . ?

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 O2 C7 O1 -179.7(5) . . . . ?
Zn1 O2 C7 C5 1.7(6) . . . . ?
Zn1 N1 C5 C7 -3.5(6) . . . . ?
Zn1 N1 C5 C4 178.3(5) . . . . ?
Zn1 N1 C6 C2 -179.8(4) . . . . ?
Zn2 O5 C14 O4 -178.8(5) . . . . ?
Zn2 O5 C14 C12 3.3(6) . . . . ?
Zn2 O8 C21 O9 174.2(5) . . . . ?
Zn2 O8 C21 C19 -6.0(6) . . . . ?
Zn2 N3 C20 C16 179.5(4) . . . . ?
Zn2 N3 C19 C21 3.7(6) . . . . ?
Zn2 N3 C19 C18 -179.2(5) . . . . ?
Zn2 N2 C13 C9 -174.4(4) . . . . ?
Zn2 N2 C12 C14 -6.2(6) . . . . ?
Zn2 N2 C12 C11 174.5(5) . . . . ?
O5 C14 C12 N2 2.2(8) . . . . ?
O5 C14 C12 C11 -178.5(6) . . . . ?
N3 C20 C16 C17 -0.2(9) . . . . ?
N3 C20 C16 C15 176.8(5) . . . . ?
N3 C19 C21 O8 1.3(7) . . . . ?
N3 C19 C21 O9 -178.9(5) . . . . ?
N3 C19 C18 C17 -0.3(10) . . . . ?
N1 C5 C7 O2 1.3(8) . . . . ?
N1 C5 C7 O1 -177.4(5) . . . . ?
N1 C5 C4 C3 1.1(9) . . . . ?
O4 C14 C12 N2 -175.9(5) . . . . ?
O4 C14 C12 C11 3.4(9) . . . . ?
N2 C13 C9 C10 -0.2(9) . . . . ?
N2 C13 C9 C8 -178.9(6) . . . . ?
N2 C12 C11 C10 1.3(10) . . . . ?
C20 N3 C19 C21 -176.2(5) . . . . ?
C20 N3 C19 C18 0.9(8) . . . . ?
C20 C16 C17 C18 0.8(9) . . . . ?
C20 C16 C15 F9 149.1(6) . . . . ?
C20 C16 C15 F8 -91.3(7) . . . . ?
C20 C16 C15 F7 28.5(8) . . . . ?
C13 N2 C12 C14 177.1(5) . . . . ?
C13 N2 C12 C11 -2.1(8) . . . . ?
C13 C9 C10 C11 -0.6(10) . . . . ?
C13 C9 C8 F4 97.7(9) . . . . ?
C13 C9 C8 F5 -133.8(7) . . . . ?
C13 C9 C8 F6 -20.5(9) . . . . ?
C5 N1 C6 C2 0.1(8) . . . . ?
C7 C5 C4 C3 -177.1(6) . . . . ?
C19 N3 C20 C16 -0.7(8) . . . . ?
C14 C12 C11 C10 -177.9(6) . . . . ?
C21 C19 C18 C17 176.7(6) . . . . ?
C3 C2 C6 N1 1.9(9) . . . . ?
C3 C2 C1 F3 154.5(6) . . . . ?
C3 C2 C1 F2 32.8(9) . . . . ?
C3 C2 C1 F1 -86.7(8) . . . . ?
C16 C17 C18 C19 -0.6(10) . . . . ?
C12 N2 C13 C9 1.6(8) . . . . ?
C2 C3 C4 C5 0.9(10) . . . . ?
C6 N1 C5 C7 176.6(5) . . . . ?
C6 N1 C5 C4 -1.6(8) . . . . ?
C6 C2 C1 F3 -27.4(9) . . . . ?
C6 C2 C1 F2 -149.1(6) . . . . ?
C6 C2 C1 F1 91.4(7) . . . . ?
C1 C2 C6 N1 -176.2(5) . . . . ?
C17 C16 C15 F9 -33.9(8) . . . . ?
C17 C16 C15 F8 85.7(7) . . . . ?
C17 C16 C15 F7 -154.6(6) . . . . ?
C4 C5 C7 O2 179.6(5) . . . . ?
C4 C5 C7 O1 0.9(9) . . . . ?
C4 C3 C2 C6 -2.4(9) . . . . ?
C4 C3 C2 C1 175.7(6) . . . . ?
C9 C10 C11 C12 0.1(11) . . . . ?
C15 C16 C17 C18 -176.2(6) . . . . ?
C10 C9 C8 F4 -81.0(10) . . . . ?
C10 C9 C8 F5 47.5(10) . . . . ?
C10 C9 C8 F6 160.8(7) . . . . ?
C18 C19 C21 O8 -175.8(5) . . . . ?
C18 C19 C21 O9 4.0(8) . . . . ?
C8 C9 C10 C11 178.1(6) . . . . ?

_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_1
_audit_block_doi                 10.5517/ccdc.csd.cc2h63wq
_database_code_depnum_ccdc_archive 'CCDC 2299793'
loop_
_audit_author_name
_audit_author_address
ZhuXiaoshuang
;Ningxia University
China
;
_audit_update_record             
;
2023-10-08 deposited with the CCDC.	2024-02-07 downloaded from the CCDC.
;
_audit_creation_date             2019-07-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C28 H20 F12 N4 O12 Zn2)'
_chemical_formula_sum            'C14 H10 F6 N2 O6 Zn'
_chemical_formula_weight         481.61
_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'
F F 0.0171 0.0103 '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                   12.0060(5)
_cell_length_b                   9.9453(4)
_cell_length_c                   7.2624(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.9081(12)
_cell_angle_gamma                90
_cell_volume                     829.67(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9304
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      3.55
_shelx_estimated_absorpt_T_max   0.797
_shelx_estimated_absorpt_T_min   0.764
_exptl_absorpt_coefficient_mu    1.584
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0893 before and 0.0409 after correction.
The Ratio of minimum to maximum transmission is 0.7444.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.928
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12653
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.547
_diffrn_reflns_theta_min         3.547
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_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                1742
_reflns_number_total             1902
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.732
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1902
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.086
_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)+(0.0470P)²+0.8360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0863
_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
 H3B_$1-H5_$2
 2.2 with sigma of 0.02
3.a Rotating group:
 O3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5)
;
_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
Zn1 Zn 0.500000 0.500000 0.500000 0.01912(12) Uani 1 2 d S T P . .
O1 O 0.43347(14) 0.54716(15) 0.7331(2) 0.0279(3) Uani 1 1 d . . . . .
O3 O 0.62208(14) 0.36882(15) 0.6689(2) 0.0265(3) Uani 1 1 d . . . . .
H3A H 0.587780 0.307374 0.717951 0.040 Uiso 1 1 d GR . . . .
H3B H 0.666206 0.409857 0.769570 0.040 Uiso 1 1 d DGR . . . .
F2 F 0.11574(15) 0.53627(19) 0.9633(3) 0.0499(4) Uani 1 1 d . . . . .
F3 F 0.00502(13) 0.41393(19) 0.7429(3) 0.0557(5) Uani 1 1 d . . . . .
O2 O 0.33805(13) 0.61832(14) 0.9340(2) 0.0238(3) Uani 1 1 d . . . . .
F1 F 0.11886(14) 0.55662(17) 0.6698(2) 0.0482(4) Uani 1 1 d . . . . .
N1 N 0.36796(15) 0.15419(16) 0.8978(2) 0.0197(3) Uani 1 1 d . . . . .
C1 C 0.39676(17) 0.28226(19) 0.8738(3) 0.0193(4) Uani 1 1 d . . . . .
H1 H 0.473182 0.300164 0.876092 0.023 Uiso 1 1 calc R . . . .
C7 C 0.36705(17) 0.5299(2) 0.8352(3) 0.0174(4) Uani 1 1 d . . . . .
C4 C 0.17283(18) 0.2277(2) 0.8520(3) 0.0263(4) Uani 1 1 d . . . . .
H4 H 0.095837 0.205792 0.840818 0.032 Uiso 1 1 calc R . . . .
C5 C 0.25613(18) 0.1287(2) 0.8835(3) 0.0241(4) Uani 1 1 d . . . . .
H5 H 0.233982 0.040236 0.895487 0.029 Uiso 1 1 calc DR . . . .
C2 C 0.31958(17) 0.38947(19) 0.8459(3) 0.0173(4) Uani 1 1 d . . . . .
C3 C 0.20431(17) 0.3607(2) 0.8370(3) 0.0210(4) Uani 1 1 d . . . . .
C6 C 0.1116(2) 0.4678(3) 0.8042(4) 0.0332(5) 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 O1 2.1236(14) . ?
Zn1 O1 2.1236(14) 3_666 ?
Zn1 O3 2.0759(15) . ?
Zn1 O3 2.0759(15) 3_666 ?
Zn1 N1 2.1752(17) 4_565 ?
Zn1 N1 2.1752(17) 2_656 ?
O1 C7 1.249(2) . ?
O3 H3A 0.8690 . ?
O3 H3B 0.8696 . ?
F2 C6 1.329(3) . ?
F3 C6 1.338(3) . ?
O2 C7 1.247(2) . ?
F1 C6 1.338(3) . ?
N1 C1 1.344(2) . ?
N1 C5 1.341(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.388(3) . ?
C7 C2 1.518(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(3) . ?
C4 C3 1.388(3) . ?
C5 H5 0.9300 . ?
C2 C3 1.396(3) . ?
C3 C6 1.509(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O1 180.00(7) 3_666 . ?
O1 Zn1 N1 91.26(6) . 4_565 ?
O1 Zn1 N1 88.74(6) 3_666 4_565 ?
O1 Zn1 N1 91.26(6) 3_666 2_656 ?
O1 Zn1 N1 88.74(6) . 2_656 ?
O3 Zn1 O1 91.85(6) . . ?
O3 Zn1 O1 91.85(6) 3_666 3_666 ?
O3 Zn1 O1 88.15(6) . 3_666 ?
O3 Zn1 O1 88.15(6) 3_666 . ?
O3 Zn1 O3 180.0 3_666 . ?
O3 Zn1 N1 94.47(6) 3_666 2_656 ?
O3 Zn1 N1 94.47(6) . 4_565 ?
O3 Zn1 N1 85.53(6) 3_666 4_565 ?
O3 Zn1 N1 85.53(6) . 2_656 ?
N1 Zn1 N1 180.00(6) 4_565 2_656 ?
C7 O1 Zn1 153.66(14) . . ?
Zn1 O3 H3A 110.3 . . ?
Zn1 O3 H3B 110.8 . . ?
H3A O3 H3B 103.4 . . ?
C1 N1 Zn1 121.52(13) . 2_646 ?
C5 N1 Zn1 120.45(13) . 2_646 ?
C5 N1 C1 117.33(17) . . ?
N1 C1 H1 117.9 . . ?
N1 C1 C2 124.10(18) . . ?
C2 C1 H1 117.9 . . ?
O1 C7 C2 118.08(17) . . ?
O2 C7 O1 125.29(19) . . ?
O2 C7 C2 116.60(17) . . ?
C5 C4 H4 120.2 . . ?
C5 C4 C3 119.62(19) . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 122.74(18) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C1 C2 C7 117.98(17) . . ?
C1 C2 C3 117.38(17) . . ?
C3 C2 C7 124.59(17) . . ?
C4 C3 C2 118.71(18) . . ?
C4 C3 C6 118.68(19) . . ?
C2 C3 C6 122.57(19) . . ?
F2 C6 F3 106.5(2) . . ?
F2 C6 F1 107.6(2) . . ?
F2 C6 C3 112.6(2) . . ?
F3 C6 C3 111.1(2) . . ?
F1 C6 F3 106.3(2) . . ?
F1 C6 C3 112.29(19) . . ?

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 O1 C7 O2 -155.4(2) . . . . ?
Zn1 O1 C7 C2 26.4(4) . . . . ?
Zn1 N1 C1 C2 -166.88(14) 2_646 . . . ?
Zn1 N1 C5 C4 168.52(16) 2_646 . . . ?
O1 C7 C2 C1 45.9(3) . . . . ?
O1 C7 C2 C3 -136.8(2) . . . . ?
O2 C7 C2 C1 -132.54(19) . . . . ?
O2 C7 C2 C3 44.9(3) . . . . ?
N1 C1 C2 C7 175.72(18) . . . . ?
N1 C1 C2 C3 -1.9(3) . . . . ?
C1 N1 C5 C4 -2.1(3) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C1 C2 C3 C6 -179.06(19) . . . . ?
C7 C2 C3 C4 -178.83(18) . . . . ?
C7 C2 C3 C6 3.5(3) . . . . ?
C4 C3 C6 F2 102.6(2) . . . . ?
C4 C3 C6 F3 -16.8(3) . . . . ?
C4 C3 C6 F1 -135.7(2) . . . . ?
C5 N1 C1 C2 3.6(3) . . . . ?
C5 C4 C3 C2 2.8(3) . . . . ?
C5 C4 C3 C6 -179.4(2) . . . . ?
C2 C3 C6 F2 -79.7(3) . . . . ?
C2 C3 C6 F3 160.8(2) . . . . ?
C2 C3 C6 F1 42.0(3) . . . . ?
C3 C4 C5 N1 -1.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
