# Electronic Supplementary Material (ESI) 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. 
# 
#######################################################################

data_l
_database_code_depnum_ccdc_archive 'CCDC 2343053'
loop_
_audit_author_name
_audit_author_address
'Dong-Dong Zhou'
;Sun Yat Sen University
China
;
_audit_update_record             
;
2024-04-02 deposited with the CCDC.	2024-04-19 downloaded from the CCDC.
;
_audit_creation_date             2024-04-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H6 F6 N4 O2'
_chemical_formula_sum            'C16 H6 F6 N4 O2'
_chemical_formula_weight         400.25
_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 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   4.7256(3)
_cell_length_b                   16.4363(11)
_cell_length_c                   9.9536(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.715(6)
_cell_angle_gamma                90
_cell_volume                     772.76(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2789
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.0080
_cell_measurement_theta_min      5.1820
_shelx_estimated_absorpt_T_max   0.866
_shelx_estimated_absorpt_T_min   0.756
_exptl_absorpt_coefficient_mu    1.483
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
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    1.720
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1340
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        66.621
_diffrn_reflns_theta_max         66.621
_diffrn_reflns_theta_min         5.197
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1196
_reflns_number_total             1340
_reflns_special_details          
;
 _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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1340
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0788
_refine_ls_restrained_S_all      1.045
_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)+(0.0807P)²+1.2301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1939
_refine_ls_wR_factor_ref         0.1991
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.599(10)
 0.401(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Riding coordinates:
 N1(H1)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8)
;
_atom_sites_solution_hydrogens   mixed
_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
F1 F 0.8379(7) 0.88813(18) 0.6114(3) 0.0735(10) Uani 1 1 d . . . . .
F2 F 1.1743(6) 0.8346(2) 0.5039(3) 0.0783(10) Uani 1 1 d . . . . .
F3 F 0.8289(7) 0.88864(18) 0.3967(3) 0.0718(9) Uani 1 1 d . . . . .
O1 O -0.0084(7) 0.50300(17) 0.6425(2) 0.0472(8) Uani 1 1 d . . . . .
N1 N 0.6474(7) 0.7294(2) 0.6157(3) 0.0423(9) Uani 1 1 d . . . . .
H1 H 0.6626 0.7465 0.7004 0.053(13) Uiso 1 1 d R . . . .
N2 N 0.6577(7) 0.7262(2) 0.3912(3) 0.0414(8) Uani 1 1 d . . . . .
C1 C 0.8939(9) 0.8428(3) 0.5042(3) 0.0485(11) Uani 1 1 d . . . . .
C2 C 0.7388(9) 0.7638(3) 0.5025(3) 0.0420(10) Uani 1 1 d . . . . .
C3 C 0.4936(9) 0.6622(2) 0.4344(3) 0.0398(9) Uani 1 1 d . . . . .
C4 C 0.4850(9) 0.6640(2) 0.5752(3) 0.0396(9) Uani 1 1 d . . . . .
C5 C 0.3184(9) 0.6100(2) 0.6466(3) 0.0416(10) Uani 1 1 d . . . . .
H5 H 0.3146 0.6112 0.7419 0.050 Uiso 1 1 calc R U . . .
C6 C 0.1603(9) 0.5550(2) 0.5726(4) 0.0401(10) Uani 1 1 d . . . . .
C7 C 0.1691(9) 0.5524(2) 0.4312(4) 0.0395(10) Uani 1 1 d . . . . .
C8 C 0.3370(9) 0.6044(2) 0.3608(3) 0.0413(10) Uani 1 1 d . . . . .
H8 H 0.3465 0.6012 0.2657 0.050 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
F1 C1 1.334(5) . ?
F2 C1 1.332(5) . ?
F3 C1 1.336(5) . ?
O1 C6 1.373(5) . ?
O1 C7 1.382(5) 3_566 ?
N1 H1 0.8899 . ?
N1 C2 1.344(5) . ?
N1 C4 1.374(5) . ?
N2 C2 1.315(5) . ?
N2 C3 1.383(5) . ?
C1 C2 1.492(7) . ?
C3 C4 1.403(5) . ?
C3 C8 1.399(6) . ?
C4 C5 1.395(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.372(6) . ?
C6 C7 1.410(5) . ?
C7 O1 1.382(5) 3_566 ?
C7 C8 1.372(6) . ?
C8 H8 0.9500 . ?

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
C6 O1 C7 117.4(3) . 3_566 ?
C2 N1 H1 130.1 . . ?
C2 N1 C4 105.9(3) . . ?
C4 N1 H1 123.6 . . ?
C2 N2 C3 104.3(3) . . ?
F1 C1 F3 106.2(4) . . ?
F1 C1 C2 112.7(3) . . ?
F2 C1 F1 106.2(4) . . ?
F2 C1 F3 105.1(4) . . ?
F2 C1 C2 113.6(4) . . ?
F3 C1 C2 112.4(3) . . ?
N1 C2 C1 121.8(3) . . ?
N2 C2 N1 114.5(4) . . ?
N2 C2 C1 123.4(3) . . ?
N2 C3 C4 109.1(3) . . ?
N2 C3 C8 130.3(3) . . ?
C8 C3 C4 120.5(4) . . ?
N1 C4 C3 106.1(3) . . ?
N1 C4 C5 131.9(3) . . ?
C5 C4 C3 121.9(4) . . ?
C4 C5 H5 121.6 . . ?
C6 C5 C4 116.9(3) . . ?
C6 C5 H5 121.6 . . ?
O1 C6 C7 121.5(4) . . ?
C5 C6 O1 116.9(3) . . ?
C5 C6 C7 121.6(4) . . ?
O1 C7 C6 121.2(3) 3_566 . ?
C8 C7 O1 117.1(3) . 3_566 ?
C8 C7 C6 121.7(4) . . ?
C3 C8 H8 121.3 . . ?
C7 C8 C3 117.4(3) . . ?
C7 C8 H8 121.3 . . ?

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
F1 C1 C2 N1 -24.0(6) . . . . ?
F1 C1 C2 N2 149.5(4) . . . . ?
F2 C1 C2 N1 96.9(5) . . . . ?
F2 C1 C2 N2 -89.7(5) . . . . ?
F3 C1 C2 N1 -144.0(4) . . . . ?
F3 C1 C2 N2 29.5(6) . . . . ?
O1 C6 C7 O1 -0.2(6) . . . 3_566 ?
O1 C6 C7 C8 179.9(4) . . . . ?
O1 C7 C8 C3 178.1(3) 3_566 . . . ?
N1 C4 C5 C6 174.1(4) . . . . ?
N2 C3 C4 N1 -0.4(4) . . . . ?
N2 C3 C4 C5 175.4(3) . . . . ?
N2 C3 C8 C7 -173.4(4) . . . . ?
C2 N1 C4 C3 1.1(4) . . . . ?
C2 N1 C4 C5 -174.1(4) . . . . ?
C2 N2 C3 C4 -0.4(4) . . . . ?
C2 N2 C3 C8 175.7(4) . . . . ?
C3 N2 C2 N1 1.2(5) . . . . ?
C3 N2 C2 C1 -172.7(4) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?
C4 N1 C2 N2 -1.5(5) . . . . ?
C4 N1 C2 C1 172.5(4) . . . . ?
C4 C3 C8 C7 2.4(6) . . . . ?
C4 C5 C6 O1 -178.6(3) . . . . ?
C4 C5 C6 C7 1.0(6) . . . . ?
C5 C6 C7 O1 -179.8(4) . . . 3_566 ?
C5 C6 C7 C8 0.3(6) . . . . ?
C6 C7 C8 C3 -1.9(6) . . . . ?
C7 O1 C6 C5 179.8(3) 3_566 . . . ?
C7 O1 C6 C7 0.2(6) 3_566 . . . ?
C8 C3 C4 N1 -177.0(3) . . . . ?
C8 C3 C4 C5 -1.2(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.599(10)
2 0.401(10)

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 2343054'
loop_
_audit_author_name
_audit_author_address
'Dong-Dong Zhou'
;Sun Yat Sen University
China
;
_audit_update_record             
;
2024-03-25 deposited with the CCDC.	2024-04-19 downloaded from the CCDC.
;
_audit_creation_date             2024-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            MAF-50
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.08(C216 H96 F72 N48 O60 Zn24)'
_chemical_formula_sum            'C18 H8 F6 N4 O5 Zn2'
_chemical_formula_weight         605.02
_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 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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      hexagonal
_space_group_IT_number           193
_space_group_name_H-M_alt        'P 63/m c m'
_space_group_name_Hall           '-P 6c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'-y, -x, -z'
'-x+y, y, -z'
'x, x-y, -z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'x, y, -z-1/2'
'-y, x-y, -z-1/2'
'-x+y, -x, -z-1/2'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'y, x, z'
'x-y, -y, z'
'-x, -x+y, z'

_cell_length_a                   26.1617(4)
_cell_length_b                   26.1617(4)
_cell_length_c                   16.6663(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     9878.7(4)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    7768
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      72.1680
_cell_measurement_theta_min      4.2740
_shelx_estimated_absorpt_T_max   0.765
_shelx_estimated_absorpt_T_min   0.734
_exptl_absorpt_coefficient_mu    2.357
_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            ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3576
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20445
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.497
_diffrn_reflns_theta_max         67.497
_diffrn_reflns_theta_min         3.902
_diffrn_ambient_temperature      250.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2499
_reflns_number_total             3205
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.593
_refine_diff_density_min         -1.118
_refine_diff_density_rms         0.140
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3205
_refine_ls_number_restraints     156
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0891
_refine_ls_restrained_S_all      1.103
_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)+(0.1575P)²+43.4545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2478
_refine_ls_wR_factor_ref         0.2666
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F2-F3 = F3-F1 = F1-F2
 2.15 with sigma of 0.01
 F5-C13
 1.5 with sigma of 0.01
 F3-C3 = F1-C3 = F2-C3
 1.35 with sigma of 0.01
 C3-C4
 1.5 with sigma of 0.01
 C8-C9
 1.5 with sigma of 0.02
 C13-C9
 1.5 with sigma of 0.02
 F2-F3 \\sim F3-F1 \\sim F1-F2
 with sigma of 0.01
 F1-C3 \\sim F3-C3 \\sim F2-C3
 with sigma of 0.01
3. Restrained planarity
 N3, C9, C13, C14
 with sigma of 0.02
 N2, C8, C9, C10
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim C3: within 2A with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(O3) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.002
Uanis(C2) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C13) \\sim Ueq, Uanis(N3) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(F6) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F7) \\sim
Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(F6) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(F7) \\sim Ueq, Uanis(N3) \\sim
Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq,
Uanis(O5) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(F6) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C3) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C8) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C10) \\sim
Ueq, Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(O4) \\sim Ueq: with
sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O4) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C10)
\\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(F5) \\sim Ueq,
Uanis(F4) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
5. Others
 Sof(F6)=Sof(N3)=Sof(C14)=Sof(C15)=Sof(H15)=Sof(C16)=1-FVAR(1)
 Sof(F7)=Sof(O5)=Sof(C13)=0.5*(1-FVAR(2))
 Sof(F4)=Sof(O4)=Sof(C8)=0.5*FVAR(2)
 Sof(F5)=Sof(N2)=Sof(C10)=Sof(C11)=Sof(H11)=Sof(C12)=FVAR(1)
 Fixed Sof: F1(0.5) F2(0.5) F3(0.5) H1A(0.5) H1B(0.5) H1C(0.5)
6.a Riding coordinates:
 O1(H1), C1(H1A,H1B,H1C)
6.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C11(H11), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.22978(3) 0.36436(4) 0.43302(4) 0.0430(4) Uani 1 1 d . . . . .
F1 F 0.1966(4) 0.2211(4) 0.4883(6) 0.108(2) Uani 0.5 1 d D U . A -1
F2 F 0.2394(4) 0.1883(3) 0.4120(6) 0.089(2) Uani 0.5 1 d D U . A -1
F3 F 0.2087(4) 0.2450(5) 0.3644(6) 0.106(2) Uani 0.5 1 d D U . A -1
F4 F 0.3235(7) 0.3688(8) 0.2500 0.142(5) Uani 0.717(6) 2 d S TU P B 1
F5 F 0.3288(4) 0.4411(5) 0.3185(6) 0.106(4) Uani 0.717(6) 1 d D U . B 1
F6 F 0.3254(8) 0.4149(8) 0.3083(11) 0.059(5) Uani 0.283(6) 1 d . U . B 2
F7 F 0.306(3) 0.465(3) 0.2500 0.21(2) Uani 0.283(6) 2 d S TU P B 2
O1 O 0.16088(13) 0.3218(3) 0.5000 0.0423(12) Uani 1 2 d S T P B .
H1 H 0.1424 0.2848 0.5000 0.051 Uiso 1 2 d RS T P . .
O2 O 0.2605(2) 0.4457(2) 0.4680(4) 0.0690(14) Uani 1 1 d . . . . .
O3 O 0.46883(14) 0.53117(14) 0.5000 0.092(3) Uani 1 2 d S TU P C 1
O4 O 0.0000 0.3096(5) 0.3341(5) 0.071(3) Uani 0.717(6) 2 d S TU P B 1
O5 O 0.0000 0.1776(10) 0.3302(12) 0.054(6) Uani 0.283(6) 2 d S TU P B 2
N1 N 0.2931(2) 0.3430(2) 0.4509(3) 0.0446(11) Uani 1 1 d . . . . .
N2 N 0.2085(4) 0.3687(5) 0.3172(5) 0.047(2) Uani 0.717(6) 1 d . U . B 1
N3 N 0.2036(8) 0.3419(7) 0.3177(12) 0.025(4) Uani 0.283(6) 1 d . U . B 2
C1 C 0.2690(4) 0.5380(9) 0.5000 0.144(7) Uani 1 2 d S TU P . .
H1A H 0.3079 0.5513 0.5229 0.216 Uiso 0.5 1 d R . . D -1
H1B H 0.2476 0.5513 0.5317 0.216 Uiso 0.5 1 d R . . D -1
H1C H 0.2729 0.5513 0.4454 0.216 Uiso 0.5 1 d R . . D -1
C2 C 0.2352(3) 0.4703(5) 0.5000 0.070(3) Uani 1 2 d S TU P . .
C3 C 0.2362(3) 0.2362(3) 0.4272(6) 0.099(2) Uani 1 2 d DS TU P . .
C4 C 0.2922(3) 0.2922(3) 0.4421(5) 0.047(2) Uani 1 2 d DS T P A .
C5 C 0.3518(3) 0.3822(3) 0.4685(4) 0.0478(14) Uani 1 1 d . . . . .
C6 C 0.3803(3) 0.4429(3) 0.4800(5) 0.0564(18) Uani 1 1 d . . . . .
H6 H 0.3597 0.4638 0.4796 0.068 Uiso 1 1 calc R . . . .
C7 C 0.4391(3) 0.4704(3) 0.4918(6) 0.072(3) Uani 1 1 d . . . . .
C8 C 0.3018(6) 0.3969(7) 0.2500 0.076(5) Uani 0.717(6) 2 d DS TU P B 1
C9 C 0.2363(4) 0.3754(5) 0.2500 0.059(3) Uani 1 2 d DS T P . .
C10 C 0.1516(4) 0.3509(4) 0.2918(5) 0.055(3) Uani 0.717(6) 1 d . U . B 1
C11 C 0.1009(4) 0.3368(5) 0.3362(5) 0.060(3) Uani 0.717(6) 1 d . U . B 1
H11 H 0.1007 0.3368 0.3926 0.072 Uiso 0.717(6) 1 calc R . . B 1
C12 C 0.0510(4) 0.3228(5) 0.2918(5) 0.061(3) Uani 0.717(6) 1 d . U . B 1
C13 C 0.2923(7) 0.4209(8) 0.2500 0.032(6) Uani 0.283(6) 2 d DS TU P B 2
C14 C 0.1493(7) 0.3003(8) 0.2905(11) 0.034(4) Uani 0.283(6) 1 d . U . B 2
C15 C 0.0996(7) 0.2597(10) 0.3372(12) 0.043(5) Uani 0.283(6) 1 d . U . B 2
H15 H 0.0987 0.2604 0.3935 0.052 Uiso 0.283(6) 1 calc R . . B 2
C16 C 0.0511(8) 0.2178(11) 0.2891(12) 0.052(6) Uani 0.283(6) 1 d . U . B 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 O1 1.931(3) . ?
Zn1 O2 1.950(5) . ?
Zn1 N1 2.017(5) . ?
Zn1 N2 2.028(9) . ?
Zn1 N3 2.027(19) . ?
F1 C3 1.362(6) . ?
F2 C3 1.321(6) . ?
F3 C3 1.353(6) . ?
F4 C8 1.13(2) . ?
F5 C8 1.525(14) . ?
F6 C13 1.36(2) . ?
F7 C13 1.01(7) . ?
O1 Zn1 1.931(3) 11_556 ?
O1 H1 0.8372 . ?
O2 C2 1.252(7) . ?
O3 C7 1.384(7) 10_666 ?
O3 C7 1.384(7) . ?
O4 C12 1.393(10) . ?
O4 C12 1.393(10) 24 ?
O5 C16 1.40(2) . ?
O5 C16 1.40(2) 24 ?
N1 C4 1.324(6) . ?
N1 C5 1.387(7) . ?
N2 C9 1.299(9) . ?
N2 C10 1.385(11) . ?
N3 C9 1.423(19) . ?
N3 C14 1.36(3) . ?
C1 H1A 0.9743 . ?
C1 H1B 0.9529 . ?
C1 H1C 0.9624 . ?
C1 C2 1.53(2) . ?
C2 O2 1.252(7) 11_556 ?
C3 F1 1.362(6) 22 ?
C3 C4 1.488(8) . ?
C4 N1 1.324(6) 22 ?
C5 C5 1.379(11) 22 ?
C5 C6 1.390(9) . ?
C6 H6 0.9400 . ?
C6 C7 1.348(9) . ?
C7 C7 1.416(12) 22 ?
C8 F5 1.524(14) 16_556 ?
C8 C9 1.512(13) . ?
C9 N2 1.299(9) 16_556 ?
C9 N3 1.423(19) 16_556 ?
C9 C13 1.349(15) . ?
C10 C10 1.394(17) 16_556 ?
C10 C11 1.398(13) . ?
C11 H11 0.9400 . ?
C11 C12 1.380(12) . ?
C12 C12 1.392(17) 16_556 ?
C13 F6 1.36(2) 16_556 ?
C14 C14 1.35(4) 16_556 ?
C14 C15 1.43(3) . ?
C15 H15 0.9400 . ?
C15 C16 1.44(3) . ?
C16 C16 1.30(4) 16_556 ?

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 O2 102.3(2) . . ?
O1 Zn1 N1 114.41(18) . . ?
O1 Zn1 N2 112.3(2) . . ?
O1 Zn1 N3 107.3(5) . . ?
O2 Zn1 N1 108.1(2) . . ?
O2 Zn1 N2 101.4(3) . . ?
O2 Zn1 N3 119.7(5) . . ?
N1 Zn1 N2 116.2(3) . . ?
N1 Zn1 N3 105.4(5) . . ?
Zn1 O1 Zn1 120.0(3) 11_556 . ?
Zn1 O1 H1 120.0 11_556 . ?
Zn1 O1 H1 120.0 . . ?
C2 O2 Zn1 130.9(6) . . ?
C7 O3 C7 118.8(7) 10_666 . ?
C12 O4 C12 112.3(10) . 24 ?
C16 O5 C16 112(2) . 24 ?
C4 N1 Zn1 131.1(4) . . ?
C4 N1 C5 102.8(5) . . ?
C5 N1 Zn1 125.8(4) . . ?
C9 N2 Zn1 132.6(6) . . ?
C9 N2 C10 102.6(7) . . ?
C10 N2 Zn1 123.4(6) . . ?
C9 N3 Zn1 124.1(11) . . ?
C14 N3 Zn1 127.8(14) . . ?
C14 N3 C9 107.1(15) . . ?
H1A C1 H1B 110.4 . . ?
H1A C1 H1C 109.8 . . ?
H1B C1 H1C 111.5 . . ?
C2 C1 H1A 108.1 . . ?
C2 C1 H1B 108.5 . . ?
C2 C1 H1C 108.4 . . ?
O2 C2 O2 127.0(11) . 11_556 ?
O2 C2 C1 116.5(5) . . ?
O2 C2 C1 116.5(5) 11_556 . ?
F1 C3 F1 48.2(7) 22 . ?
F1 C3 C4 113.1(8) 22 . ?
F1 C3 C4 113.1(8) . . ?
F2 C3 F1 105.7(6) . . ?
F2 C3 F1 63.6(6) . 22 ?
F2 C3 F3 107.7(6) . . ?
F2 C3 C4 117.9(5) . . ?
F3 C3 F1 103.7(5) . . ?
F3 C3 F1 137.0(9) . 22 ?
F3 C3 C4 107.8(8) . . ?
N1 C4 N1 117.2(7) 22 . ?
N1 C4 C3 121.4(3) . . ?
N1 C4 C3 121.4(3) 22 . ?
N1 C5 C6 129.7(5) . . ?
C5 C5 N1 108.5(3) 22 . ?
C5 C5 C6 121.6(3) 22 . ?
C5 C6 H6 121.7 . . ?
C7 C6 C5 116.5(6) . . ?
C7 C6 H6 121.7 . . ?
O3 C7 C7 120.6(4) . 22 ?
C6 C7 O3 117.5(6) . . ?
C6 C7 C7 121.8(4) . 22 ?
F4 C8 F5 107.5(10) . . ?
F4 C8 F5 107.5(10) . 16_556 ?
F4 C8 C9 127.0(15) . . ?
F5 C8 F5 96.9(13) 16_556 . ?
C9 C8 F5 106.9(8) . 16_556 ?
C9 C8 F5 106.9(8) . . ?
N2 C9 N2 119.0(9) . 16_556 ?
N2 C9 C8 120.3(5) 16_556 . ?
N2 C9 C8 120.3(5) . . ?
N3 C9 N3 104.9(16) . 16_556 ?
C13 C9 N3 126.7(8) . 16_556 ?
C13 C9 N3 126.7(8) . . ?
N2 C10 C10 107.8(5) . 16_556 ?
N2 C10 C11 130.3(8) . . ?
C10 C10 C11 121.9(5) 16_556 . ?
C10 C11 H11 122.2 . . ?
C12 C11 C10 115.7(8) . . ?
C12 C11 H11 122.2 . . ?
C11 C12 O4 117.1(8) . . ?
C11 C12 C12 122.4(5) . 16_556 ?
C12 C12 O4 120.5(5) 16_556 . ?
F6 C13 F6 91(2) . 16_556 ?
F7 C13 F6 105(3) . . ?
F7 C13 F6 105(3) . 16_556 ?
F7 C13 C9 127(4) . . ?
C9 C13 F6 111.7(12) . . ?
C9 C13 F6 111.7(12) . 16_556 ?
N3 C14 C15 127.6(17) . . ?
C14 C14 N3 109.4(11) 16_556 . ?
C14 C14 C15 123.0(10) 16_556 . ?
C14 C15 H15 123.5 . . ?
C14 C15 C16 113.1(17) . . ?
C16 C15 H15 123.5 . . ?
O5 C16 C15 116.6(18) . . ?
C16 C16 O5 119.4(11) 16_556 . ?
C16 C16 C15 123.9(11) 16_556 . ?

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 C2 O2 15.3(4) . . . 11_556 ?
Zn1 O2 C2 C1 -164.7(4) . . . . ?
Zn1 N1 C4 N1 173.4(3) . . . 22 ?
Zn1 N1 C4 C3 -9.7(13) . . . . ?
Zn1 N1 C5 C5 -174.1(3) . . . 22 ?
Zn1 N1 C5 C6 1.9(11) . . . . ?
Zn1 N2 C9 N2 170.9(4) . . . 16_556 ?
Zn1 N2 C9 C8 -15.5(16) . . . . ?
Zn1 N2 C10 C10 -170.4(5) . . . 16_556 ?
Zn1 N2 C10 C11 11.9(17) . . . . ?
Zn1 N3 C9 N3 176.7(3) . . . 16_556 ?
Zn1 N3 C9 C13 11(2) . . . . ?
Zn1 N3 C14 C14 177.9(9) . . . 16_556 ?
Zn1 N3 C14 C15 -5(3) . . . . ?
F1 C3 C4 N1 114.7(8) . . . 22 ?
F1 C3 C4 N1 62.0(10) 22 . . 22 ?
F1 C3 C4 N1 -62.0(10) . . . . ?
F1 C3 C4 N1 -114.7(8) 22 . . . ?
F2 C3 C4 N1 -9.2(12) . . . 22 ?
F2 C3 C4 N1 174.0(8) . . . . ?
F3 C3 C4 N1 52.0(10) . . . . ?
F3 C3 C4 N1 -131.2(8) . . . 22 ?
F4 C8 C9 N2 -93.2(9) . . . 16_556 ?
F4 C8 C9 N2 93.2(9) . . . . ?
F5 C8 C9 N2 -35.3(13) . . . . ?
F5 C8 C9 N2 138.2(12) . . . 16_556 ?
F5 C8 C9 N2 -138.2(12) 16_556 . . . ?
F5 C8 C9 N2 35.3(13) 16_556 . . 16_556 ?
N1 C5 C6 C7 -176.1(8) . . . . ?
N2 C10 C11 C12 177.4(11) . . . . ?
N3 C9 C13 F6 131.7(16) . . . 16_556 ?
N3 C9 C13 F6 31(2) . . . . ?
N3 C9 C13 F6 -31(2) 16_556 . . 16_556 ?
N3 C9 C13 F6 -131.7(16) 16_556 . . . ?
N3 C9 C13 F7 98.5(13) 16_556 . . . ?
N3 C9 C13 F7 -98.5(13) . . . . ?
N3 C14 C15 C16 -174.0(19) . . . . ?
C4 N1 C5 C5 0.4(6) . . . 22 ?
C4 N1 C5 C6 176.4(8) . . . . ?
C5 N1 C4 N1 -0.7(11) . . . 22 ?
C5 N1 C4 C3 176.2(8) . . . . ?
C5 C5 C6 C7 -0.5(10) 22 . . . ?
C5 C6 C7 O3 177.3(7) . . . . ?
C5 C6 C7 C7 0.5(10) . . . 22 ?
C7 O3 C7 C6 -176.8(11) 10_666 . . . ?
C7 O3 C7 C7 -0.005(2) 10_666 . . 22 ?
C9 N2 C10 C10 -2.3(10) . . . 16_556 ?
C9 N2 C10 C11 -180.0(12) . . . . ?
C9 N3 C14 C14 8.9(14) . . . 16_556 ?
C9 N3 C14 C15 -174.3(18) . . . . ?
C10 N2 C9 N2 4.4(18) . . . 16_556 ?
C10 N2 C9 C8 178.0(5) . . . . ?
C10 C10 C11 C12 0.1(13) 16_556 . . . ?
C10 C11 C12 O4 -178.8(11) . . . . ?
C10 C11 C12 C12 -0.1(13) . . . 16_556 ?
C12 O4 C12 C11 -152.5(8) 24 . . . ?
C12 O4 C12 C12 28.8(15) 24 . . 16_556 ?
C14 N3 C9 N3 -14(2) . . . 16_556 ?
C14 N3 C9 C13 -179.7(6) . . . . ?
C14 C14 C15 C16 2(2) 16_556 . . . ?
C14 C15 C16 O5 -178(2) . . . . ?
C14 C15 C16 C16 -3(2) . . . 16_556 ?
C16 O5 C16 C15 141.8(18) 24 . . . ?
C16 O5 C16 C16 -34(3) 24 . . 16_556 ?

_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 0.000 0.000 -0.488 950.8 17.7 ?
2 -0.420 0.007 -0.178 3133.4 699.5 ?

_olex2_submission_special_instructions 'No special instructions were received'
